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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoIUCrDATA
ISSN: 2414-3146
Volume 3| Part 3| March 2018| x180427
https://doi.org/10.1107/S2414314618004273

tert-Butyl 4-{3-[6-(4-meth­­oxy­phen­yl)-2-methyl­pyrimidin-4-yl]quinolin-2-yl}piperazine-1-carboxyl­ate

CROSSMARK_Color_square_no_text.svg
Sumati Anthal,a Vikram. D. Singh,b N. R. Desai,c D. B. Arunakumar,c S. Sreenivasa,d Kamnib and Rajni Kanta*

aDepartment of Physics, University of Jammu, Jammu Tawi 180 006, India, bSchool of Physics, Shri Mata Vaishno Devi University, Katra 182 320, J&K, India, cDepartment of Chemistry, University College of Science, Tumkur University Tumkur 572 103, India, and dDepartment of Studies and Research in Chemistry, Tumkur University, Tumkur 572 103, Karnataka, India
*Correspondence e-mail: rkant.ju@gmail.com

Edited by A. J. Lough, University of Toronto, Canada (Received 5 February 2018; accepted 13 March 2018; online 15 March 2018)

The asymmetric unit of the title compound, C30H33N5O3, contains two independent mol­ecules, A and B. In mol­ecule A, the tert-butyl 4-methyl­piperazine-1-carboxyl­ate group was refined as disordered over two sets of sites with an occupancy ratio of 0.821 (4):0.179 (4). The piperazine ring adopts a chair conformation in both mol­ecules. The dihedral angles between the pyrimidine ring and meth­oxy­phenyl ring are 20.27 (14) and 8.72 (11)° for mol­ecules A and B, respectively. The quinoline ring system makes dihedral angles of 30.68 (11) and 37.76 (10)° with the pyrimidine ring in mol­ecules A and B, respectively. In the crystal, C—H⋯O hydrogen bonds link the mol­ecules into chains along [100].

CCDC reference: 1829297

Similar articles
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[Scheme 3D1]
Chemical scheme
[Scheme 1]

Structure description

Pyrimidine and its derivatives have a diverse array of biological and pharmacological activities including anti­convulsant, anti­bacterial, anti­fungal, anti­viral and anti­cancer properties (Jain et al., 2006[Jain, K. S., Chitre, T. S., Miniyar, P. B., Kathiravan, M. K., Bendre, V. S., Veer, V. S., Shahane, S. R. & Shishoo, C. J. (2006). Curr. Sci. 90, 793-803.]). An SAR study of the pyrimidine nucleus revealed that substitution at different positions may lead to compounds with a variation in their biological activities (Khanage et al., 2012[Khanage, S. G., Raju, S. A., Mohite, P. B. & Pandhare, R. B. (2012). Adv. Pharma. Bull. 2, 213-222.]). Compounds with a pyrimidine ring substituted at the 2 and 4 positions with keto or amino or mixed keto–amino groups have shown anti­cancer, anti­viral, anti­bacterial and anti­fungal activity and are used in the treatment of respiratory tract infections and liver disorders. Substitution at the 5 and 6 positions with a heterocyclic ring or a substituted aryl ring leads to anti­cancer, anti­viral, anti­bacterial and vasodilation activity and such compounds are also used in the treatment of urinary tract infections (Selvam et al., 2012[Selvam, T. P., James, C. R., Dniandev, P. V. & Valzita, S. K. (2012). Res. Pharm. 2, 1-9.]). On the other hand, quinoline derivatives also find importance owing to their wide occurrence in natural products and in biologically active compounds (Markees et al., 1970[Markees, D. G., Dewey, V. C. & Kidder, G. W. (1970). J. Med. Chem. 13, 324-326.]; Campbell et al., 1988[Campbell, S. F., Hardstone, J. D. & Palmer, M. J. (1988). J. Med. Chem. 31, 1031-1035.]; Kalluraya & Sreenivasa, 1998[Kalluraya, B. & Sreenivasa, S. (1998). Farmaco, 53, 399-404.]). As part of our studies in this area, we now describe the synthesis and structure of the title compound.

The asymmetric unit of the title compound comprises two independent mol­ecules, A and B (Figs. 1[link] and 2[link]). In both the mol­ecules, the piperazine ring adopts a chair conformation. In the major occupancy component of disordered mol­ecule A [0.821 (5) occupancy], the best mirror plane passes through atoms N4A and N5A and the best twofold rotational axis bis­ects the N5A—C23A bond [asymmetry parameter Cs(N4A) = 2.53 and C2(N5A—C23A) = 1.91] whereas for the minor [0.179 (5)] occupancy component, the best mirror plane passes through atoms C23C and C25C and the best twofold rotational axis bis­ects the C22C—C23C bond [asymmetry parameter Cs(C23C) = 1.06 and C2(C22C—C23C) = 0.71]. In mol­ecule B, the best mirror plane passes through atoms N4B and N5B and the best twofold rotational axis bis­ects the N5B—C24B bond [asymmetry parameter Cs(N4B) = 0.54 and C2(N5B—C24B) = 5.2] (Duax & Norton, 1975[Duax, W. L. & Norton, D. A. (1975). Atlas of Steroid Structures, Vol. 1. New York: Plenum Press.]). All bond lengths are in normal ranges and are comparable with those in previously reported related structures (Prasath et al., 2010[Prasath, R., Sarveswari, S., Vijayakumar, V., Narasimhamurthy, T. & Tiekink, E. R. T. (2010). Acta Cryst. E66, o1110.], 2011[Prasath, R., Bhavana, P., Ng, S. W. & Tiekink, E. R. T. (2011). Acta Cryst. E67, o796-o797.]; Sharma et al., 2017[Sharma, D. K., Desai, N. R., Sreenivasa, S., Anthal, S. & Kant, R. (2017). IUCrData, 2, x171600.]; Singh et al., 2018[Singh, V. D., Anthal, S., Desai, N. R., Arunakumar, D. B., Sreenivasa, S., Kamni & Kant, R. (2018). IUCr Data 3, x180030.]). The dihedral angle between the pyrimidine and meth­oxy­phenyl rings is 20.27 (14)° in mol­ecule A and 8.72 (11)° in mol­ecule B while the pyrimidine ring makes a dihedral angle of 30.68 (11)° in A and 37.76 (10)° in B with the quinoline ring system. The quinoline units are essentially planar with a maximum deviation of 0.0851 (1) Å for atom C21A and 0.0607 (1) Å for C21B.

[Figure 1]
Figure 1
The mol­ecular structure of mol­ecule A showing 30% probability displacement ellipsoids. The minor disorder component is shown with green dashed bonds. H atoms are omitted for clarity.
[Figure 2]
Figure 2
The mol­ecular structure of mol­ecule B showing 30% probability displacement ellipsoids.

In the crystal, adjacent mol­ecules are linked by C—H⋯O hydrogen bonds, forming chains along [100] (Table 1[link] and Fig. 3[link]).

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
C7B—H7BA⋯O2Bi 0.93 2.40 3.141 (2) 136
Symmetry code: (i) x+1, y, z.
[Figure 3]
Figure 3
Partial packing plot. Dashed lines indicate the C—H⋯O inter­molecular inter­actions forming chains along [100]. H atoms not involved in these inter­actions have been omitted for clarity.

Synthesis and crystallization

2-(4-N-Boc-piperazin-1-yl) quinoline chalcone (1000 mg, 0.00258 mmol), acetamidine hydro­chloride (199 mg, 0.002211 mmol) and NaOH (253 mg, 0.00633 mmol) were refluxed for 12 h in ethanol. The progress of the reaction was monitored by thin layer chromatography. After the completion of reaction, the reaction mixture was poured into water and extracted with ethyl acetate. The organic layer was washed with water, dried and concentrated under vacuum using a rotary evaporator to obtain a solid that was purified by column chromatography using 60–120 mesh silica gel. Crystals of the title compound were obtained by recrystallization from ethyl acetate solution.

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2[link]. Disorder was modeled for the tert-butyl 4-methyl piperazine-1-carboxyl­ate group in mol­ecule A with an occupancy ratio of 0.821 (4):0.179 (4). In addition, the methyl H atoms attached to C12A and C12B are also disordered with occupancy ratios of 0.68 (4):0.32 (4) and 0.53 (4):0.47 (4), respectively.

Table 2
Experimental details

Crystal data
Chemical formula C30H33N5O3
Mr 511.61
Crystal system, space group Triclinic, P[\overline{1}]
Temperature (K) 293
a, b, c (Å) 11.0894 (6), 12.6875 (6), 20.8953 (9)
α, β, γ (°) 83.663 (4), 75.335 (4), 86.259 (4)
V (Å3) 2824.6 (2)
Z 4
Radiation type Mo Kα
μ (mm−1) 0.08
Crystal size (mm) 0.30 × 0.20 × 0.20
 
Data collection
Diffractometer Oxford Diffraction Xcalibur Sapphire3
Absorption correction Multi-scan (CrysAlis RED; Oxford Diffraction, 2010[Oxford Diffraction (2010). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.])
Tmin, Tmax 0.869, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections 19560, 9886, 5244
Rint 0.042
(sin θ/λ)max (Å−1) 0.595
 
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.065, 0.181, 1.03
No. of reflections 9886
No. of parameters 751
No. of restraints 32
H-atom treatment H-atom parameters constrained
Δρmax, Δρmin (e Å−3) 0.27, −0.21
Computer programs: CrysAlis PRO (Oxford Diffraction, 2010[Oxford Diffraction (2010). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]), SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]), SHELXL2016 (Sheldrick, 2015[Sheldrick, G. M. (2015). Acta Cryst. C71, 3-8.]), ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).

Structural data

CCDC reference: 1829297

Crystal structure: contains datablocks I, New_Global_Publ_Block. DOI: https://doi.org/10.1107/S2414314618004273/lh4032sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314618004273/lh4032Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2414314618004273/lh4032Isup3.cml

checkCIF report


Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2010); cell refinement: CrysAlis PRO (Oxford Diffraction, 2010); data reduction: CrysAlis PRO (Oxford Diffraction, 2010); program(s) used to solve structure: SHELXL97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2016 (Sheldrick, 2015); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: PLATON (Spek, 2009).

tert-Butyl 4-{3-[6-(4-methoxyphenyl)-2-methylpyrimidin-4-yl]quinolin-2-yl}piperazine-1-carboxylate top
Crystal data top
C30H33N5O3Z = 4
Mr = 511.61F(000) = 1088
Triclinic, P1Dx = 1.203 Mg m−3
a = 11.0894 (6) ÅMo Kα radiation, λ = 0.71073 Å
b = 12.6875 (6) ÅCell parameters from 4885 reflections
c = 20.8953 (9) Åθ = 3.8–26.6°
α = 83.663 (4)°µ = 0.08 mm−1
β = 75.335 (4)°T = 293 K
γ = 86.259 (4)°Block, white
V = 2824.6 (2) Å30.30 × 0.20 × 0.20 mm
Data collection top
Oxford Diffraction Xcalibur Sapphire3
diffractometer		9886 independent reflections
Radiation source: fine-focus sealed tube5244 reflections with I > 2σ(I)
Detector resolution: 6.1049 pixels mm-1Rint = 0.042
ω scansθmax = 25.0°, θmin = 3.6°
Absorption correction: multi-scan
(CrysAlis RED; Oxford Diffraction, 2010)		h = −13→13
Tmin = 0.869, Tmax = 1.000k = −15→15
19560 measured reflectionsl = −24→24
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.065 w = 1/[σ2(Fo2) + (0.056P)2 + 0.4039P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.181(Δ/σ)max < 0.001
S = 1.03Δρmax = 0.27 e Å−3
9886 reflectionsΔρmin = −0.21 e Å−3
751 parametersExtinction correction: SHELXL2016 (Sheldrick, 2015), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
32 restraintsExtinction coefficient: 0.0055 (7)
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. All H atoms were positioned geometrically and were treated as riding on their parent C atoms, with C—H distances of 0.93–0.97 Å; and with Uiso(H) = 1.2Ueq(C), except for the methyl groups where Uiso(H) = 1.5Ueq(C).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
O1A0.4112 (2)0.24904 (15)0.89015 (12)0.0782 (7)
N1A0.4291 (2)0.74137 (18)0.90707 (12)0.0547 (7)
N2A0.3208 (2)0.90807 (18)0.89406 (12)0.0549 (7)
N3A−0.0740 (2)0.95687 (18)0.83629 (12)0.0535 (7)
C1A0.3435 (4)0.1902 (2)0.8577 (2)0.0910 (13)
H1AA0.3643780.1159250.8647130.137*
H1AB0.3647410.2124120.8108970.137*
H1AC0.2556350.2025710.8755080.137*
C2A0.3901 (3)0.3566 (2)0.88660 (16)0.0557 (8)
C3A0.4511 (3)0.4105 (2)0.92207 (17)0.0631 (9)
H3AA0.5034220.3732180.9458280.076*
C4A0.4352 (3)0.5183 (2)0.92263 (16)0.0577 (8)
H4AA0.4771790.5533360.9467960.069*
C5A0.3575 (3)0.5764 (2)0.88772 (13)0.0439 (7)
C6A0.2974 (3)0.5202 (2)0.85269 (15)0.0553 (8)
H6AA0.2444210.5567920.8290520.066*
C7A0.3135 (3)0.4115 (2)0.85170 (16)0.0607 (9)
H7AA0.2723510.3759250.8273920.073*
C8A0.3410 (3)0.6926 (2)0.88887 (13)0.0441 (7)
C9A0.2394 (3)0.7501 (2)0.87395 (13)0.0461 (7)
H9AA0.1774160.7163770.8620800.055*
C10A0.2319 (3)0.8586 (2)0.87707 (13)0.0447 (7)
C11A0.4142 (3)0.8467 (2)0.90806 (16)0.0573 (8)
C12A0.5128 (3)0.9007 (3)0.9286 (2)0.0883 (12)
H12D0.5230390.8669990.9704470.132*0.68 (4)
H12E0.4882400.9740790.9329710.132*0.68 (4)
H12F0.5903170.8957350.8955410.132*0.68 (4)
H12X0.5446920.9575430.8955260.132*0.32 (4)
H12Y0.5794900.8504630.9330010.132*0.32 (4)
H12Z0.4774140.9288070.9704320.132*0.32 (4)
C13A0.1206 (3)0.9268 (2)0.86981 (14)0.0453 (7)
C14A0.0897 (3)1.0104 (2)0.90780 (14)0.0514 (8)
H14B0.1443251.0275880.9319430.062*
C15A−0.0226 (3)1.0711 (2)0.91138 (14)0.0517 (8)
C16A−0.0554 (3)1.1607 (2)0.94699 (15)0.0657 (9)
H16B−0.0005881.1829850.9694150.079*
C17A−0.1658 (4)1.2153 (3)0.94927 (17)0.0763 (11)
H17B−0.1856621.2758670.9717210.092*
C18A−0.2483 (4)1.1787 (3)0.91735 (18)0.0811 (12)
H18B−0.3250761.2144410.9199400.097*
C19A−0.2206 (3)1.0926 (3)0.88262 (17)0.0693 (10)
H19B−0.2784271.0700250.8621750.083*
C20A−0.1046 (3)1.0368 (2)0.87717 (15)0.0534 (8)
C21A0.0360 (3)0.9066 (2)0.83122 (14)0.0471 (7)
N4A0.0650 (6)0.8296 (5)0.7862 (3)0.046 (2)0.821 (4)
N5A0.1156 (4)0.7165 (3)0.67279 (16)0.0595 (10)0.821 (4)
C22A0.1768 (6)0.8494 (5)0.7325 (3)0.0569 (17)0.821 (4)
H22A0.2432420.8691940.7507500.068*0.821 (4)
H22B0.1594890.9080890.7017800.068*0.821 (4)
C23A0.2187 (5)0.7528 (4)0.6955 (2)0.0584 (12)0.821 (4)
H23A0.2880560.7699400.6576500.070*0.821 (4)
H23B0.2467300.6967090.7244920.070*0.821 (4)
C24A0.0010 (5)0.7023 (3)0.7245 (2)0.0648 (12)0.821 (4)
H24A0.0129950.6439830.7567430.078*0.821 (4)
H24B−0.0649060.6845830.7051320.078*0.821 (4)
C25A−0.0367 (5)0.8018 (4)0.7589 (3)0.0580 (14)0.821 (4)
H25A−0.0543390.8592740.7275140.070*0.821 (4)
H25B−0.1116480.7904130.7943760.070*0.821 (4)
O2A0.0461 (3)0.6256 (2)0.60292 (15)0.0806 (10)0.821 (4)
O3A0.2454 (3)0.6779 (3)0.57806 (16)0.0736 (10)0.821 (4)
C26A0.1296 (4)0.6692 (3)0.6160 (2)0.0618 (12)0.821 (4)
C27A0.2787 (4)0.6395 (4)0.51153 (19)0.0716 (13)0.821 (4)
C28A0.1984 (12)0.6966 (7)0.4686 (3)0.115 (5)0.821 (4)
H28D0.1126010.6805920.4878110.173*0.821 (4)
H28E0.2240410.6736040.4247670.173*0.821 (4)
H28F0.2077610.7717340.4660980.173*0.821 (4)
C29A0.4124 (4)0.6716 (4)0.4865 (2)0.1048 (19)0.821 (4)
H29D0.4605970.6380890.5158670.157*0.821 (4)
H29E0.4157760.7472310.4849350.157*0.821 (4)
H29F0.4459580.6497470.4427100.157*0.821 (4)
C30A0.2686 (11)0.5201 (6)0.5179 (5)0.122 (6)0.821 (4)
H30D0.3081030.4883970.5516690.182*0.821 (4)
H30E0.3089710.4934010.4762540.182*0.821 (4)
H30F0.1822200.5028110.5299390.182*0.821 (4)
N4C0.085 (2)0.836 (2)0.7815 (14)0.047 (12)*0.179 (4)
N5C0.1755 (15)0.7272 (14)0.6637 (7)0.060 (6)*0.179 (4)
C22C0.206 (2)0.8579 (18)0.7344 (14)0.031 (6)*0.179 (4)
H22E0.2626620.8801940.7582370.037*0.179 (4)
H22F0.1942620.9158380.7018710.037*0.179 (4)
C23C0.2630 (15)0.763 (2)0.6988 (11)0.072 (10)*0.179 (4)
H23E0.3408640.7813750.6672390.087*0.179 (4)
H23F0.2806180.7058940.7305950.087*0.179 (4)
C24C0.0558 (16)0.7045 (16)0.7084 (10)0.058 (8)*0.179 (4)
H24E0.0651080.6442000.7398540.070*0.179 (4)
H24F−0.0009130.6858850.6832680.070*0.179 (4)
C25C0.0015 (17)0.7984 (18)0.7456 (13)0.050 (8)*0.179 (4)
H25E−0.0172920.8557140.7144190.060*0.179 (4)
H25F−0.0762940.7790320.7770630.060*0.179 (4)
O2C0.3282 (13)0.6920 (11)0.5751 (7)0.073 (5)*0.179 (4)
O3C0.1338 (15)0.6351 (13)0.5861 (7)0.083 (6)*0.179 (4)
C26C0.2201 (14)0.6809 (16)0.6060 (7)0.046 (6)*0.179 (4)
C27C0.1653 (14)0.5955 (12)0.5196 (7)0.070 (6)*0.179 (4)
C28C0.204 (4)0.6879 (19)0.4671 (11)0.065 (13)*0.179 (4)
H28A0.2246560.6627580.4238250.098*0.179 (4)
H28B0.1365050.7398990.4702070.098*0.179 (4)
H28C0.2754990.7193160.4741400.098*0.179 (4)
C29C0.0406 (14)0.5576 (13)0.5176 (9)0.076 (6)*0.179 (4)
H29A0.0477170.5291270.4760500.114*0.179 (4)
H29B0.0139940.5034440.5534920.114*0.179 (4)
H29C−0.0195170.6160140.5220180.114*0.179 (4)
C30C0.264 (3)0.507 (2)0.5163 (17)0.10 (2)*0.179 (4)
H30A0.2843810.4821740.4730140.145*0.179 (4)
H30B0.3379960.5338770.5242380.145*0.179 (4)
H30C0.2341720.4502450.5493860.145*0.179 (4)
O1B0.4659 (2)1.16589 (17)0.28836 (13)0.0853 (8)
N1B0.4623 (2)0.66522 (19)0.30835 (12)0.0557 (7)
N2B0.3734 (2)0.52099 (18)0.27451 (12)0.0551 (7)
N3B0.0359 (2)0.55788 (18)0.16688 (12)0.0520 (6)
N4B0.0356 (2)0.66254 (17)0.25152 (11)0.0498 (6)
N5B−0.1124 (2)0.7906 (2)0.34538 (12)0.0630 (8)
C1B0.3905 (4)1.2467 (3)0.26348 (19)0.0943 (13)
H1BA0.4225971.3147780.2645310.141*
H1BB0.3064941.2436040.2905430.141*
H1BC0.3912241.2364300.2185480.141*
C2B0.4366 (3)1.0626 (2)0.28821 (16)0.0606 (9)
C3B0.3370 (3)1.0326 (2)0.26817 (17)0.0663 (9)
H3BA0.2824131.0834860.2542460.080*
C4B0.3181 (3)0.9249 (2)0.26880 (16)0.0619 (9)
H4BA0.2494470.9045750.2558000.074*
C5B0.3986 (3)0.8478 (2)0.28824 (14)0.0488 (7)
C6B0.4954 (3)0.8812 (2)0.31091 (15)0.0598 (9)
H6BA0.5488750.8307660.3262070.072*
C7B0.5143 (3)0.9874 (2)0.31135 (16)0.0647 (9)
H7BA0.5794211.0080000.3272250.078*
C8B0.3852 (3)0.7341 (2)0.28273 (14)0.0471 (7)
C9B0.3023 (3)0.6982 (2)0.25148 (14)0.0506 (8)
H9BA0.2506630.7457400.2325520.061*
C10B0.2974 (3)0.5898 (2)0.24882 (13)0.0468 (7)
C11B0.4525 (3)0.5623 (2)0.30273 (15)0.0577 (9)
C12B0.5392 (4)0.4855 (3)0.33093 (18)0.0829 (12)
H12A0.4947060.4241780.3533270.124*0.53 (4)
H12B0.5711960.5190330.3618980.124*0.53 (4)
H12C0.6072000.4643570.2955660.124*0.53 (4)
H12H0.6206950.5142010.3205340.124*0.47 (4)
H12I0.5442050.4193460.3119630.124*0.47 (4)
H12J0.5082010.4740220.3782950.124*0.47 (4)
C13B0.2175 (3)0.5448 (2)0.21209 (14)0.0460 (7)
C14B0.2663 (3)0.4644 (2)0.17423 (14)0.0513 (8)
H14A0.3429920.4328130.1771780.062*
C15B0.2034 (3)0.4276 (2)0.13054 (15)0.0507 (8)
C16B0.2510 (3)0.3443 (2)0.09124 (16)0.0642 (9)
H16A0.3260800.3093440.0940950.077*
C17B0.1869 (4)0.3149 (3)0.04889 (18)0.0759 (10)
H17A0.2172220.2585150.0236530.091*
C18B0.0765 (4)0.3686 (3)0.04325 (18)0.0782 (11)
H18A0.0344900.3488400.0134480.094*
C19B0.0286 (3)0.4503 (3)0.08085 (16)0.0684 (9)
H19A−0.0453620.4858120.0764050.082*
C20B0.0911 (3)0.4806 (2)0.12621 (15)0.0505 (8)
C21B0.0952 (3)0.5863 (2)0.20887 (14)0.0459 (7)
C22B−0.0774 (3)0.7163 (2)0.23884 (15)0.0597 (9)
H22C−0.1469010.6696420.2544010.072*
H22D−0.0663870.7348480.1914770.072*
C23B−0.1044 (3)0.8159 (2)0.27487 (15)0.0661 (10)
H23C−0.0387720.8653910.2559230.079*
H23D−0.1825330.8495380.2690370.079*
C24B−0.0071 (3)0.7270 (3)0.36064 (16)0.0706 (10)
H24C−0.0252270.7048960.4079320.085*
H24D0.0664150.7693260.3490800.085*
C25B0.0178 (3)0.6312 (2)0.32272 (14)0.0609 (9)
H25C0.0918850.5925830.3305940.073*
H25D−0.0518740.5846880.3381090.073*
O2B−0.2597 (2)0.9194 (2)0.37400 (12)0.0920 (9)
O3B−0.1626 (2)0.8354 (2)0.44866 (12)0.0929 (9)
C26B−0.1844 (3)0.8539 (3)0.38876 (17)0.0651 (9)
C27B−0.2333 (5)0.8896 (4)0.5058 (2)0.0995 (14)
C28B−0.3655 (5)0.8573 (5)0.5203 (3)0.181 (3)
H28G−0.4017640.8866280.4848210.271*
H28H−0.4119780.8833390.5612240.271*
H28I−0.3676020.7813320.5242970.271*
C29B−0.1713 (6)0.8443 (5)0.5595 (2)0.182 (3)
H29G−0.0829310.8530150.5443780.274*
H29H−0.1876090.7702190.5699410.274*
H29I−0.2037140.8808770.5985060.274*
C30B−0.2271 (7)1.0048 (4)0.4932 (3)0.186 (3)
H30G−0.2767431.0304620.4627990.280*
H30H−0.1420851.0236230.4743880.280*
H30I−0.2584721.0362470.5342930.280*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O1A0.0893 (18)0.0390 (12)0.108 (2)0.0004 (12)−0.0272 (16)−0.0079 (12)
N1A0.0546 (16)0.0462 (14)0.0688 (17)−0.0004 (12)−0.0213 (14)−0.0169 (12)
N2A0.0581 (16)0.0428 (14)0.0682 (18)−0.0056 (12)−0.0198 (14)−0.0126 (12)
N3A0.0581 (17)0.0504 (14)0.0517 (16)0.0005 (13)−0.0136 (13)−0.0055 (12)
C1A0.101 (3)0.048 (2)0.125 (4)−0.014 (2)−0.020 (3)−0.023 (2)
C2A0.059 (2)0.0412 (18)0.065 (2)−0.0049 (15)−0.0103 (17)−0.0049 (15)
C3A0.063 (2)0.0474 (18)0.085 (2)0.0040 (16)−0.0331 (19)−0.0003 (17)
C4A0.060 (2)0.0477 (18)0.072 (2)−0.0038 (15)−0.0272 (18)−0.0056 (16)
C5A0.0491 (18)0.0383 (15)0.0447 (17)−0.0046 (13)−0.0109 (14)−0.0051 (13)
C6A0.064 (2)0.0456 (17)0.062 (2)0.0003 (15)−0.0264 (17)−0.0083 (15)
C7A0.079 (2)0.0421 (17)0.068 (2)−0.0072 (16)−0.0286 (19)−0.0107 (15)
C8A0.0508 (18)0.0411 (16)0.0408 (16)−0.0022 (14)−0.0095 (14)−0.0093 (12)
C9A0.0554 (19)0.0400 (16)0.0481 (17)−0.0066 (14)−0.0209 (15)−0.0056 (13)
C10A0.0523 (18)0.0391 (16)0.0438 (17)−0.0012 (14)−0.0125 (15)−0.0070 (13)
C11A0.057 (2)0.0511 (19)0.070 (2)−0.0077 (16)−0.0217 (18)−0.0173 (16)
C12A0.076 (3)0.063 (2)0.142 (4)−0.0108 (19)−0.044 (3)−0.032 (2)
C13A0.0521 (18)0.0370 (15)0.0469 (17)−0.0064 (13)−0.0117 (15)−0.0024 (13)
C14A0.060 (2)0.0443 (16)0.0505 (18)−0.0061 (15)−0.0131 (16)−0.0057 (14)
C15A0.063 (2)0.0421 (16)0.0436 (18)0.0016 (15)−0.0038 (16)−0.0019 (13)
C16A0.087 (3)0.0550 (19)0.051 (2)0.0082 (18)−0.0082 (19)−0.0168 (15)
C17A0.095 (3)0.066 (2)0.058 (2)0.019 (2)−0.003 (2)−0.0138 (17)
C18A0.083 (3)0.080 (3)0.068 (3)0.028 (2)−0.001 (2)−0.010 (2)
C19A0.063 (2)0.075 (2)0.064 (2)0.0113 (18)−0.0084 (19)−0.0092 (18)
C20A0.057 (2)0.0494 (18)0.0446 (18)0.0043 (15)−0.0003 (16)0.0020 (14)
C21A0.0544 (19)0.0398 (16)0.0439 (17)−0.0049 (14)−0.0067 (15)−0.0009 (13)
N4A0.049 (3)0.047 (3)0.044 (3)−0.007 (2)−0.0084 (18)−0.0108 (17)
N5A0.061 (3)0.071 (2)0.046 (2)−0.012 (2)−0.004 (2)−0.0205 (17)
C22A0.059 (4)0.062 (3)0.053 (3)−0.008 (3)−0.014 (3)−0.0139 (19)
C23A0.056 (3)0.074 (3)0.045 (3)−0.001 (3)−0.008 (2)−0.016 (2)
C24A0.065 (3)0.064 (3)0.066 (3)−0.015 (2)−0.007 (3)−0.021 (2)
C25A0.050 (3)0.066 (3)0.059 (3)−0.007 (2)−0.009 (3)−0.017 (2)
O2A0.088 (3)0.092 (2)0.068 (2)−0.0160 (19)−0.0164 (19)−0.0331 (16)
O3A0.073 (3)0.101 (2)0.047 (2)−0.0036 (19)−0.0081 (19)−0.0239 (18)
C26A0.066 (3)0.059 (3)0.062 (3)−0.006 (2)−0.017 (3)−0.010 (2)
C27A0.076 (3)0.100 (3)0.038 (2)0.011 (3)−0.011 (2)−0.021 (2)
C28A0.115 (7)0.174 (9)0.064 (4)0.007 (5)−0.044 (4)−0.002 (4)
C29A0.092 (4)0.163 (5)0.057 (3)0.006 (4)−0.005 (3)−0.039 (3)
C30A0.159 (9)0.108 (7)0.103 (7)0.031 (4)−0.031 (4)−0.061 (5)
O1B0.108 (2)0.0496 (14)0.108 (2)−0.0091 (13)−0.0438 (17)−0.0097 (13)
N1B0.0653 (17)0.0537 (15)0.0557 (16)0.0090 (13)−0.0282 (14)−0.0135 (12)
N2B0.0672 (18)0.0518 (15)0.0516 (15)0.0078 (13)−0.0257 (14)−0.0075 (12)
N3B0.0561 (16)0.0524 (14)0.0489 (15)−0.0057 (12)−0.0149 (13)−0.0043 (12)
N4B0.0564 (16)0.0491 (14)0.0442 (14)0.0047 (12)−0.0156 (13)−0.0025 (11)
N5B0.0701 (18)0.0679 (17)0.0520 (17)0.0253 (14)−0.0206 (15)−0.0134 (13)
C1B0.130 (4)0.049 (2)0.106 (3)0.004 (2)−0.039 (3)0.002 (2)
C2B0.069 (2)0.050 (2)0.065 (2)−0.0040 (17)−0.0184 (19)−0.0080 (16)
C3B0.073 (2)0.053 (2)0.078 (2)0.0089 (17)−0.029 (2)−0.0076 (17)
C4B0.063 (2)0.059 (2)0.072 (2)0.0022 (17)−0.0307 (18)−0.0136 (16)
C5B0.0519 (19)0.0482 (17)0.0494 (18)0.0014 (14)−0.0178 (15)−0.0083 (14)
C6B0.060 (2)0.058 (2)0.065 (2)0.0051 (16)−0.0235 (18)−0.0092 (16)
C7B0.067 (2)0.054 (2)0.081 (2)−0.0037 (17)−0.033 (2)−0.0084 (17)
C8B0.0467 (18)0.0489 (17)0.0456 (17)0.0016 (14)−0.0130 (15)−0.0030 (14)
C9B0.0528 (19)0.0492 (18)0.0518 (18)0.0018 (14)−0.0193 (16)−0.0008 (14)
C10B0.0510 (18)0.0490 (17)0.0394 (16)−0.0004 (14)−0.0090 (14)−0.0062 (13)
C11B0.069 (2)0.058 (2)0.0498 (19)0.0130 (17)−0.0233 (17)−0.0114 (15)
C12B0.101 (3)0.070 (2)0.094 (3)0.027 (2)−0.056 (2)−0.018 (2)
C13B0.0490 (18)0.0441 (16)0.0457 (17)−0.0028 (13)−0.0143 (15)−0.0007 (13)
C14B0.0511 (19)0.0492 (17)0.0535 (19)−0.0024 (14)−0.0122 (16)−0.0058 (14)
C15B0.0499 (19)0.0531 (18)0.0503 (18)−0.0103 (15)−0.0113 (16)−0.0072 (14)
C16B0.067 (2)0.061 (2)0.066 (2)−0.0021 (17)−0.0137 (19)−0.0208 (17)
C17B0.077 (3)0.079 (2)0.074 (3)−0.006 (2)−0.012 (2)−0.0313 (19)
C18B0.084 (3)0.089 (3)0.071 (2)−0.015 (2)−0.024 (2)−0.032 (2)
C19B0.064 (2)0.082 (2)0.067 (2)−0.0052 (18)−0.0238 (19)−0.0199 (19)
C20B0.053 (2)0.0516 (17)0.0480 (18)−0.0096 (15)−0.0121 (16)−0.0074 (14)
C21B0.0525 (19)0.0441 (16)0.0416 (17)−0.0030 (14)−0.0139 (15)0.0002 (13)
C22B0.058 (2)0.070 (2)0.056 (2)0.0096 (17)−0.0245 (17)−0.0090 (16)
C23B0.081 (2)0.065 (2)0.054 (2)0.0225 (18)−0.0256 (19)−0.0060 (16)
C24B0.078 (2)0.082 (2)0.051 (2)0.027 (2)−0.0206 (19)−0.0126 (17)
C25B0.068 (2)0.063 (2)0.0486 (19)0.0104 (17)−0.0133 (17)0.0002 (16)
O2B0.099 (2)0.0923 (18)0.0857 (19)0.0430 (16)−0.0306 (16)−0.0226 (14)
O3B0.108 (2)0.112 (2)0.0537 (15)0.0459 (17)−0.0173 (15)−0.0233 (14)
C26B0.070 (2)0.062 (2)0.060 (2)0.0113 (18)−0.013 (2)−0.0101 (17)
C27B0.107 (4)0.125 (4)0.063 (3)0.032 (3)−0.012 (3)−0.037 (2)
C28B0.119 (5)0.277 (8)0.124 (5)−0.027 (5)0.031 (4)−0.060 (5)
C29B0.210 (7)0.267 (7)0.069 (3)0.102 (6)−0.041 (4)−0.060 (4)
C30B0.289 (9)0.119 (4)0.166 (6)0.028 (5)−0.067 (6)−0.073 (4)
Geometric parameters (Å, º) top
O1A—C2A1.367 (3)O2C—C26C1.218 (10)
O1A—C1A1.423 (4)O3C—C26C1.325 (9)
N1A—C11A1.337 (3)O3C—C27C1.480 (10)
N1A—C8A1.342 (3)C27C—C29C1.505 (10)
N2A—C11A1.328 (4)C27C—C30C1.511 (12)
N2A—C10A1.341 (3)C27C—C28C1.518 (12)
N3A—C21A1.325 (3)C28C—H28A0.9600
N3A—C20A1.368 (4)C28C—H28B0.9600
C1A—H1AA0.9600C28C—H28C0.9600
C1A—H1AB0.9600C29C—H29A0.9600
C1A—H1AC0.9600C29C—H29B0.9600
C2A—C7A1.365 (4)C29C—H29C0.9600
C2A—C3A1.378 (4)C30C—H30A0.9600
C3A—C4A1.369 (4)C30C—H30B0.9600
C3A—H3AA0.9300C30C—H30C0.9600
C4A—C5A1.391 (4)O1B—C2B1.371 (4)
C4A—H4AA0.9300O1B—C1B1.419 (4)
C5A—C6A1.383 (4)N1B—C11B1.338 (4)
C5A—C8A1.476 (3)N1B—C8B1.346 (3)
C6A—C7A1.380 (4)N2B—C11B1.335 (4)
C6A—H6AA0.9300N2B—C10B1.337 (3)
C7A—H7AA0.9300N3B—C21B1.314 (3)
C8A—C9A1.386 (4)N3B—C20B1.379 (3)
C9A—C10A1.382 (3)N4B—C21B1.405 (3)
C9A—H9AA0.9300N4B—C22B1.457 (3)
C10A—C13A1.491 (4)N4B—C25B1.463 (3)
C11A—C12A1.500 (4)N5B—C26B1.347 (4)
C12A—H12D0.9600N5B—C23B1.454 (4)
C12A—H12E0.9600N5B—C24B1.458 (4)
C12A—H12F0.9600C1B—H1BA0.9600
C12A—H12X0.9600C1B—H1BB0.9600
C12A—H12Y0.9600C1B—H1BC0.9600
C12A—H12Z0.9600C2B—C3B1.365 (4)
C13A—C14A1.368 (4)C2B—C7B1.375 (4)
C13A—C21A1.434 (4)C3B—C4B1.394 (4)
C14A—C15A1.411 (4)C3B—H3BA0.9300
C14A—H14B0.9300C4B—C5B1.379 (4)
C15A—C16A1.404 (4)C4B—H4BA0.9300
C15A—C20A1.406 (4)C5B—C6B1.384 (4)
C16A—C17A1.360 (4)C5B—C8B1.481 (4)
C16A—H16B0.9300C6B—C7B1.378 (4)
C17A—C18A1.390 (5)C6B—H6BA0.9300
C17A—H17B0.9300C7B—H7BA0.9300
C18A—C19A1.353 (5)C8B—C9B1.379 (4)
C18A—H18B0.9300C9B—C10B1.388 (4)
C19A—C20A1.412 (4)C9B—H9BA0.9300
C19A—H19B0.9300C10B—C13B1.486 (4)
C21A—N4A1.397 (4)C11B—C12B1.503 (4)
C21A—N4C1.422 (9)C12B—H12A0.9600
N4A—C22A1.461 (5)C12B—H12B0.9600
N4A—C25A1.464 (5)C12B—H12C0.9600
N5A—C26A1.358 (5)C12B—H12H0.9600
N5A—C24A1.452 (6)C12B—H12I0.9600
N5A—C23A1.461 (6)C12B—H12J0.9600
C22A—C23A1.505 (4)C13B—C14B1.360 (4)
C22A—H22A0.9700C13B—C21B1.437 (4)
C22A—H22B0.9700C14B—C15B1.413 (4)
C23A—H23A0.9700C14B—H14A0.9300
C23A—H23B0.9700C15B—C20B1.395 (4)
C24A—C25A1.504 (5)C15B—C16B1.403 (4)
C24A—H24A0.9700C16B—C17B1.362 (4)
C24A—H24B0.9700C16B—H16A0.9300
C25A—H25A0.9700C17B—C18B1.387 (5)
C25A—H25B0.9700C17B—H17A0.9300
O2A—C26A1.211 (5)C18B—C19B1.368 (4)
O3A—C26A1.332 (5)C18B—H18A0.9300
O3A—C27A1.474 (5)C19B—C20B1.406 (4)
C27A—C29A1.509 (6)C19B—H19A0.9300
C27A—C30A1.515 (9)C22B—C23B1.516 (4)
C27A—C28A1.516 (9)C22B—H22C0.9700
C28A—H28D0.9600C22B—H22D0.9700
C28A—H28E0.9600C23B—H23C0.9700
C28A—H28F0.9600C23B—H23D0.9700
C29A—H29D0.9600C24B—C25B1.496 (4)
C29A—H29E0.9600C24B—H24C0.9700
C29A—H29F0.9600C24B—H24D0.9700
C30A—H30D0.9600C25B—H25C0.9700
C30A—H30E0.9600C25B—H25D0.9700
C30A—H30F0.9600O2B—C26B1.211 (3)
N4C—C25C1.464 (10)O3B—C26B1.327 (4)
N4C—C22C1.468 (10)O3B—C27B1.466 (4)
N5C—C26C1.364 (9)C27B—C30B1.460 (6)
N5C—C24C1.442 (10)C27B—C28B1.495 (7)
N5C—C23C1.474 (10)C27B—C29B1.502 (6)
C22C—C23C1.508 (9)C28B—H28G0.9600
C22C—H22E0.9700C28B—H28H0.9600
C22C—H22F0.9700C28B—H28I0.9600
C23C—H23E0.9700C29B—H29G0.9600
C23C—H23F0.9700C29B—H29H0.9600
C24C—C25C1.504 (10)C29B—H29I0.9600
C24C—H24E0.9700C30B—H30G0.9600
C24C—H24F0.9700C30B—H30H0.9600
C25C—H25E0.9700C30B—H30I0.9600
C25C—H25F0.9700
C2A—O1A—C1A117.2 (3)C24C—C25C—H25F109.0
C11A—N1A—C8A116.4 (3)H25E—C25C—H25F107.8
C11A—N2A—C10A116.2 (2)C26C—O3C—C27C119.5 (11)
C21A—N3A—C20A118.1 (3)O2C—C26C—O3C126.0 (12)
O1A—C1A—H1AA109.5O2C—C26C—N5C119.8 (11)
O1A—C1A—H1AB109.5O3C—C26C—N5C113.9 (10)
H1AA—C1A—H1AB109.5O3C—C27C—C29C100.6 (10)
O1A—C1A—H1AC109.5O3C—C27C—C30C110.0 (12)
H1AA—C1A—H1AC109.5C29C—C27C—C30C113.1 (15)
H1AB—C1A—H1AC109.5O3C—C27C—C28C109.0 (11)
C7A—C2A—O1A124.7 (3)C29C—C27C—C28C110.5 (14)
C7A—C2A—C3A119.6 (3)C30C—C27C—C28C112.9 (14)
O1A—C2A—C3A115.7 (3)C27C—C28C—H28A109.5
C4A—C3A—C2A120.5 (3)C27C—C28C—H28B109.5
C4A—C3A—H3AA119.7H28A—C28C—H28B109.5
C2A—C3A—H3AA119.7C27C—C28C—H28C109.5
C3A—C4A—C5A121.2 (3)H28A—C28C—H28C109.5
C3A—C4A—H4AA119.4H28B—C28C—H28C109.5
C5A—C4A—H4AA119.4C27C—C29C—H29A109.5
C6A—C5A—C4A117.0 (3)C27C—C29C—H29B109.5
C6A—C5A—C8A122.4 (3)H29A—C29C—H29B109.5
C4A—C5A—C8A120.7 (3)C27C—C29C—H29C109.5
C7A—C6A—C5A122.1 (3)H29A—C29C—H29C109.5
C7A—C6A—H6AA119.0H29B—C29C—H29C109.5
C5A—C6A—H6AA119.0C27C—C30C—H30A109.5
C2A—C7A—C6A119.6 (3)C27C—C30C—H30B109.5
C2A—C7A—H7AA120.2H30A—C30C—H30B109.5
C6A—C7A—H7AA120.2C27C—C30C—H30C109.5
N1A—C8A—C9A120.5 (2)H30A—C30C—H30C109.5
N1A—C8A—C5A116.4 (2)H30B—C30C—H30C109.5
C9A—C8A—C5A123.1 (3)C2B—O1B—C1B117.6 (3)
C10A—C9A—C8A118.7 (3)C11B—N1B—C8B116.8 (3)
C10A—C9A—H9AA120.7C11B—N2B—C10B116.5 (2)
C8A—C9A—H9AA120.7C21B—N3B—C20B118.3 (3)
N2A—C10A—C9A121.1 (3)C21B—N4B—C22B117.4 (2)
N2A—C10A—C13A115.1 (2)C21B—N4B—C25B116.1 (2)
C9A—C10A—C13A123.4 (3)C22B—N4B—C25B110.0 (2)
N2A—C11A—N1A127.1 (3)C26B—N5B—C23B118.7 (2)
N2A—C11A—C12A116.7 (3)C26B—N5B—C24B121.9 (3)
N1A—C11A—C12A116.2 (3)C23B—N5B—C24B114.9 (2)
C11A—C12A—H12D109.5O1B—C1B—H1BA109.5
C11A—C12A—H12E109.5O1B—C1B—H1BB109.5
H12D—C12A—H12E109.5H1BA—C1B—H1BB109.5
C11A—C12A—H12F109.5O1B—C1B—H1BC109.5
H12D—C12A—H12F109.5H1BA—C1B—H1BC109.5
H12E—C12A—H12F109.5H1BB—C1B—H1BC109.5
C11A—C12A—H12X109.5C3B—C2B—O1B124.4 (3)
H12D—C12A—H12X141.1C3B—C2B—C7B120.3 (3)
H12E—C12A—H12X56.3O1B—C2B—C7B115.3 (3)
H12F—C12A—H12X56.3C2B—C3B—C4B119.3 (3)
C11A—C12A—H12Y109.5C2B—C3B—H3BA120.3
H12D—C12A—H12Y56.3C4B—C3B—H3BA120.3
H12E—C12A—H12Y141.1C5B—C4B—C3B121.5 (3)
H12F—C12A—H12Y56.3C5B—C4B—H4BA119.2
H12X—C12A—H12Y109.5C3B—C4B—H4BA119.2
C11A—C12A—H12Z109.5C4B—C5B—C6B117.4 (3)
H12D—C12A—H12Z56.3C4B—C5B—C8B121.4 (3)
H12E—C12A—H12Z56.3C6B—C5B—C8B121.2 (3)
H12F—C12A—H12Z141.1C7B—C6B—C5B121.6 (3)
H12X—C12A—H12Z109.5C7B—C6B—H6BA119.2
H12Y—C12A—H12Z109.5C5B—C6B—H6BA119.2
C14A—C13A—C21A116.9 (3)C2B—C7B—C6B119.7 (3)
C14A—C13A—C10A117.3 (3)C2B—C7B—H7BA120.1
C21A—C13A—C10A125.5 (2)C6B—C7B—H7BA120.1
C13A—C14A—C15A121.8 (3)N1B—C8B—C9B120.4 (3)
C13A—C14A—H14B119.1N1B—C8B—C5B116.2 (3)
C15A—C14A—H14B119.1C9B—C8B—C5B123.3 (2)
C16A—C15A—C20A119.9 (3)C8B—C9B—C10B118.7 (3)
C16A—C15A—C14A123.9 (3)C8B—C9B—H9BA120.6
C20A—C15A—C14A116.2 (3)C10B—C9B—H9BA120.6
C17A—C16A—C15A121.2 (4)N2B—C10B—C9B121.1 (3)
C17A—C16A—H16B119.4N2B—C10B—C13B116.5 (2)
C15A—C16A—H16B119.4C9B—C10B—C13B122.2 (3)
C16A—C17A—C18A118.6 (3)N2B—C11B—N1B126.4 (3)
C16A—C17A—H17B120.7N2B—C11B—C12B116.8 (3)
C18A—C17A—H17B120.7N1B—C11B—C12B116.8 (3)
C19A—C18A—C17A122.1 (4)C11B—C12B—H12A109.5
C19A—C18A—H18B118.9C11B—C12B—H12B109.5
C17A—C18A—H18B118.9H12A—C12B—H12B109.5
C18A—C19A—C20A120.5 (4)C11B—C12B—H12C109.5
C18A—C19A—H19B119.7H12A—C12B—H12C109.5
C20A—C19A—H19B119.7H12B—C12B—H12C109.5
N3A—C20A—C15A123.1 (3)C11B—C12B—H12H109.5
N3A—C20A—C19A119.2 (3)H12A—C12B—H12H141.1
C15A—C20A—C19A117.6 (3)H12B—C12B—H12H56.3
N3A—C21A—N4A115.7 (4)H12C—C12B—H12H56.3
N3A—C21A—N4C122.0 (13)C11B—C12B—H12I109.5
N3A—C21A—C13A123.2 (3)H12A—C12B—H12I56.3
N4A—C21A—C13A121.0 (4)H12B—C12B—H12I141.1
N4C—C21A—C13A114.5 (12)H12C—C12B—H12I56.3
C21A—N4A—C22A114.4 (5)H12H—C12B—H12I109.5
C21A—N4A—C25A116.2 (5)C11B—C12B—H12J109.5
C22A—N4A—C25A109.8 (4)H12A—C12B—H12J56.3
C26A—N5A—C24A118.7 (4)H12B—C12B—H12J56.3
C26A—N5A—C23A124.3 (4)H12C—C12B—H12J141.1
C24A—N5A—C23A114.2 (3)H12H—C12B—H12J109.5
N4A—C22A—C23A111.3 (4)H12I—C12B—H12J109.5
N4A—C22A—H22A109.4C14B—C13B—C21B116.9 (3)
C23A—C22A—H22A109.4C14B—C13B—C10B118.3 (3)
N4A—C22A—H22B109.4C21B—C13B—C10B124.6 (3)
C23A—C22A—H22B109.4C13B—C14B—C15B121.7 (3)
H22A—C22A—H22B108.0C13B—C14B—H14A119.1
N5A—C23A—C22A109.9 (4)C15B—C14B—H14A119.1
N5A—C23A—H23A109.7C20B—C15B—C16B120.3 (3)
C22A—C23A—H23A109.7C20B—C15B—C14B116.7 (3)
N5A—C23A—H23B109.7C16B—C15B—C14B123.0 (3)
C22A—C23A—H23B109.7C17B—C16B—C15B119.8 (3)
H23A—C23A—H23B108.2C17B—C16B—H16A120.1
N5A—C24A—C25A110.7 (4)C15B—C16B—H16A120.1
N5A—C24A—H24A109.5C16B—C17B—C18B120.3 (3)
C25A—C24A—H24A109.5C16B—C17B—H17A119.9
N5A—C24A—H24B109.5C18B—C17B—H17A119.9
C25A—C24A—H24B109.5C19B—C18B—C17B121.0 (4)
H24A—C24A—H24B108.1C19B—C18B—H18A119.5
N4A—C25A—C24A109.0 (4)C17B—C18B—H18A119.5
N4A—C25A—H25A109.9C18B—C19B—C20B120.0 (3)
C24A—C25A—H25A109.9C18B—C19B—H19A120.0
N4A—C25A—H25B109.9C20B—C19B—H19A120.0
C24A—C25A—H25B109.9N3B—C20B—C15B122.7 (3)
H25A—C25A—H25B108.3N3B—C20B—C19B118.6 (3)
C26A—O3A—C27A120.1 (4)C15B—C20B—C19B118.7 (3)
O2A—C26A—O3A125.9 (4)N3B—C21B—N4B117.5 (3)
O2A—C26A—N5A123.2 (4)N3B—C21B—C13B123.2 (3)
O3A—C26A—N5A110.9 (4)N4B—C21B—C13B119.2 (3)
O3A—C27A—C29A101.2 (4)N4B—C22B—C23B109.1 (3)
O3A—C27A—C30A109.8 (4)N4B—C22B—H22C109.9
C29A—C27A—C30A111.7 (6)C23B—C22B—H22C109.9
O3A—C27A—C28A110.4 (5)N4B—C22B—H22D109.9
C29A—C27A—C28A110.7 (6)C23B—C22B—H22D109.9
C30A—C27A—C28A112.5 (6)H22C—C22B—H22D108.3
C27A—C28A—H28D109.5N5B—C23B—C22B110.7 (2)
C27A—C28A—H28E109.5N5B—C23B—H23C109.5
H28D—C28A—H28E109.5C22B—C23B—H23C109.5
C27A—C28A—H28F109.5N5B—C23B—H23D109.5
H28D—C28A—H28F109.5C22B—C23B—H23D109.5
H28E—C28A—H28F109.5H23C—C23B—H23D108.1
C27A—C29A—H29D109.5N5B—C24B—C25B110.4 (3)
C27A—C29A—H29E109.5N5B—C24B—H24C109.6
H29D—C29A—H29E109.5C25B—C24B—H24C109.6
C27A—C29A—H29F109.5N5B—C24B—H24D109.6
H29D—C29A—H29F109.5C25B—C24B—H24D109.6
H29E—C29A—H29F109.5H24C—C24B—H24D108.1
C27A—C30A—H30D109.5N4B—C25B—C24B110.4 (2)
C27A—C30A—H30E109.5N4B—C25B—H25C109.6
H30D—C30A—H30E109.5C24B—C25B—H25C109.6
C27A—C30A—H30F109.5N4B—C25B—H25D109.6
H30D—C30A—H30F109.5C24B—C25B—H25D109.6
H30E—C30A—H30F109.5H25C—C25B—H25D108.1
C21A—N4C—C25C119.0 (17)C26B—O3B—C27B122.9 (3)
C21A—N4C—C22C119.2 (17)O2B—C26B—O3B124.8 (3)
C25C—N4C—C22C108.6 (12)O2B—C26B—N5B123.2 (3)
C26C—N5C—C24C123.0 (11)O3B—C26B—N5B112.0 (3)
C26C—N5C—C23C120.0 (11)C30B—C27B—O3B112.3 (4)
C24C—N5C—C23C111.6 (11)C30B—C27B—C28B110.3 (5)
N4C—C22C—C23C112.8 (12)O3B—C27B—C28B107.3 (4)
N4C—C22C—H22E109.0C30B—C27B—C29B112.9 (5)
C23C—C22C—H22E109.0O3B—C27B—C29B102.1 (3)
N4C—C22C—H22F109.0C28B—C27B—C29B111.7 (5)
C23C—C22C—H22F109.0C27B—C28B—H28G109.5
H22E—C22C—H22F107.8C27B—C28B—H28H109.5
N5C—C23C—C22C109.2 (12)H28G—C28B—H28H109.5
N5C—C23C—H23E109.8C27B—C28B—H28I109.5
C22C—C23C—H23E109.8H28G—C28B—H28I109.5
N5C—C23C—H23F109.8H28H—C28B—H28I109.5
C22C—C23C—H23F109.8C27B—C29B—H29G109.5
H23E—C23C—H23F108.3C27B—C29B—H29H109.5
N5C—C24C—C25C111.2 (12)H29G—C29B—H29H109.5
N5C—C24C—H24E109.4C27B—C29B—H29I109.5
C25C—C24C—H24E109.4H29G—C29B—H29I109.5
N5C—C24C—H24F109.4H29H—C29B—H29I109.5
C25C—C24C—H24F109.4C27B—C30B—H30G109.5
H24E—C24C—H24F108.0C27B—C30B—H30H109.5
N4C—C25C—C24C113.0 (12)H30G—C30B—H30H109.5
N4C—C25C—H25E109.0C27B—C30B—H30I109.5
C24C—C25C—H25E109.0H30G—C30B—H30I109.5
N4C—C25C—H25F109.0H30H—C30B—H30I109.5
C1A—O1A—C2A—C7A−3.2 (5)C23C—N5C—C24C—C25C55 (2)
C1A—O1A—C2A—C3A176.0 (3)C21A—N4C—C25C—C24C−165 (3)
C7A—C2A—C3A—C4A0.1 (5)C22C—N4C—C25C—C24C54 (2)
O1A—C2A—C3A—C4A−179.2 (3)N5C—C24C—C25C—N4C−55 (2)
C2A—C3A—C4A—C5A0.1 (5)C27C—O3C—C26C—O2C−2 (3)
C3A—C4A—C5A—C6A0.0 (4)C27C—O3C—C26C—N5C171.3 (17)
C3A—C4A—C5A—C8A179.8 (3)C24C—N5C—C26C—O2C−170 (2)
C4A—C5A—C6A—C7A−0.4 (4)C23C—N5C—C26C—O2C−18 (3)
C8A—C5A—C6A—C7A179.8 (3)C24C—N5C—C26C—O3C16 (3)
O1A—C2A—C7A—C6A178.8 (3)C23C—N5C—C26C—O3C168.1 (19)
C3A—C2A—C7A—C6A−0.4 (5)C26C—O3C—C27C—C29C−176.8 (17)
C5A—C6A—C7A—C2A0.5 (5)C26C—O3C—C27C—C30C64 (2)
C11A—N1A—C8A—C9A−1.7 (4)C26C—O3C—C27C—C28C−61 (2)
C11A—N1A—C8A—C5A179.9 (2)C1B—O1B—C2B—C3B−2.6 (5)
C6A—C5A—C8A—N1A−160.9 (3)C1B—O1B—C2B—C7B178.5 (3)
C4A—C5A—C8A—N1A19.3 (4)O1B—C2B—C3B—C4B178.6 (3)
C6A—C5A—C8A—C9A20.8 (4)C7B—C2B—C3B—C4B−2.7 (5)
C4A—C5A—C8A—C9A−159.0 (3)C2B—C3B—C4B—C5B−1.0 (5)
N1A—C8A—C9A—C10A1.1 (4)C3B—C4B—C5B—C6B3.7 (5)
C5A—C8A—C9A—C10A179.4 (2)C3B—C4B—C5B—C8B−174.0 (3)
C11A—N2A—C10A—C9A−0.6 (4)C4B—C5B—C6B—C7B−2.9 (4)
C11A—N2A—C10A—C13A172.7 (2)C8B—C5B—C6B—C7B174.9 (3)
C8A—C9A—C10A—N2A0.1 (4)C3B—C2B—C7B—C6B3.5 (5)
C8A—C9A—C10A—C13A−172.7 (2)O1B—C2B—C7B—C6B−177.6 (3)
C10A—N2A—C11A—N1A0.0 (5)C5B—C6B—C7B—C2B−0.7 (5)
C10A—N2A—C11A—C12A−178.7 (3)C11B—N1B—C8B—C9B−1.0 (4)
C8A—N1A—C11A—N2A1.2 (5)C11B—N1B—C8B—C5B−178.9 (3)
C8A—N1A—C11A—C12A179.9 (3)C4B—C5B—C8B—N1B−174.6 (3)
N2A—C10A—C13A—C14A−29.4 (4)C6B—C5B—C8B—N1B7.8 (4)
C9A—C10A—C13A—C14A143.8 (3)C4B—C5B—C8B—C9B7.6 (4)
N2A—C10A—C13A—C21A157.0 (3)C6B—C5B—C8B—C9B−170.1 (3)
C9A—C10A—C13A—C21A−29.9 (4)N1B—C8B—C9B—C10B1.9 (4)
C21A—C13A—C14A—C15A2.8 (4)C5B—C8B—C9B—C10B179.7 (3)
C10A—C13A—C14A—C15A−171.5 (2)C11B—N2B—C10B—C9B0.3 (4)
C13A—C14A—C15A—C16A−176.7 (3)C11B—N2B—C10B—C13B174.7 (3)
C13A—C14A—C15A—C20A4.0 (4)C8B—C9B—C10B—N2B−1.6 (4)
C20A—C15A—C16A—C17A0.1 (4)C8B—C9B—C10B—C13B−175.6 (2)
C14A—C15A—C16A—C17A−179.2 (3)C10B—N2B—C11B—N1B0.7 (5)
C15A—C16A—C17A—C18A2.2 (5)C10B—N2B—C11B—C12B−179.2 (3)
C16A—C17A—C18A—C19A−2.0 (5)C8B—N1B—C11B—N2B−0.4 (5)
C17A—C18A—C19A—C20A−0.5 (5)C8B—N1B—C11B—C12B179.6 (3)
C21A—N3A—C20A—C15A3.1 (4)N2B—C10B—C13B—C14B−37.4 (4)
C21A—N3A—C20A—C19A179.1 (3)C9B—C10B—C13B—C14B136.9 (3)
C16A—C15A—C20A—N3A173.4 (3)N2B—C10B—C13B—C21B148.4 (3)
C14A—C15A—C20A—N3A−7.2 (4)C9B—C10B—C13B—C21B−37.4 (4)
C16A—C15A—C20A—C19A−2.6 (4)C21B—C13B—C14B—C15B3.9 (4)
C14A—C15A—C20A—C19A176.8 (3)C10B—C13B—C14B—C15B−170.8 (2)
C18A—C19A—C20A—N3A−173.4 (3)C13B—C14B—C15B—C20B2.4 (4)
C18A—C19A—C20A—C15A2.8 (4)C13B—C14B—C15B—C16B−179.5 (3)
C20A—N3A—C21A—N4A−176.8 (4)C20B—C15B—C16B—C17B−0.3 (5)
C20A—N3A—C21A—N4C−168.5 (17)C14B—C15B—C16B—C17B−178.2 (3)
C20A—N3A—C21A—C13A4.4 (4)C15B—C16B—C17B—C18B1.7 (5)
C14A—C13A—C21A—N3A−7.3 (4)C16B—C17B—C18B—C19B−1.4 (5)
C10A—C13A—C21A—N3A166.4 (2)C17B—C18B—C19B—C20B−0.2 (5)
C14A—C13A—C21A—N4A173.9 (4)C21B—N3B—C20B—C15B3.7 (4)
C10A—C13A—C21A—N4A−12.4 (6)C21B—N3B—C20B—C19B−179.6 (3)
C14A—C13A—C21A—N4C166.0 (16)C16B—C15B—C20B—N3B175.4 (3)
C10A—C13A—C21A—N4C−20.3 (17)C14B—C15B—C20B—N3B−6.5 (4)
N3A—C21A—N4A—C22A119.7 (5)C16B—C15B—C20B—C19B−1.3 (4)
C13A—C21A—N4A—C22A−61.4 (6)C14B—C15B—C20B—C19B176.8 (3)
N3A—C21A—N4A—C25A−9.8 (7)C18B—C19B—C20B—N3B−175.3 (3)
C13A—C21A—N4A—C25A169.0 (4)C18B—C19B—C20B—C15B1.6 (5)
C21A—N4A—C22A—C23A167.0 (6)C20B—N3B—C21B—N4B−177.9 (2)
C25A—N4A—C22A—C23A−60.2 (6)C20B—N3B—C21B—C13B3.3 (4)
C26A—N5A—C23A—C22A147.7 (5)C22B—N4B—C21B—N3B−9.6 (4)
C24A—N5A—C23A—C22A−51.5 (5)C25B—N4B—C21B—N3B123.5 (3)
N4A—C22A—C23A—N5A54.0 (6)C22B—N4B—C21B—C13B169.3 (2)
C26A—N5A—C24A—C25A−144.1 (4)C25B—N4B—C21B—C13B−57.7 (3)
C23A—N5A—C24A—C25A54.0 (5)C14B—C13B—C21B—N3B−7.0 (4)
C21A—N4A—C25A—C24A−167.2 (6)C10B—C13B—C21B—N3B167.3 (2)
C22A—N4A—C25A—C24A61.0 (5)C14B—C13B—C21B—N4B174.1 (2)
N5A—C24A—C25A—N4A−57.5 (5)C10B—C13B—C21B—N4B−11.5 (4)
C27A—O3A—C26A—O2A4.9 (6)C21B—N4B—C22B—C23B−162.8 (2)
C27A—O3A—C26A—N5A−175.2 (4)C25B—N4B—C22B—C23B61.5 (3)
C24A—N5A—C26A—O2A8.5 (6)C26B—N5B—C23B—C22B−152.0 (3)
C23A—N5A—C26A—O2A168.5 (4)C24B—N5B—C23B—C22B51.4 (4)
C24A—N5A—C26A—O3A−171.4 (3)N4B—C22B—C23B—N5B−55.4 (4)
C23A—N5A—C26A—O3A−11.4 (6)C26B—N5B—C24B—C25B153.4 (3)
C26A—O3A—C27A—C29A176.5 (4)C23B—N5B—C24B—C25B−50.8 (4)
C26A—O3A—C27A—C30A−65.3 (6)C21B—N4B—C25B—C24B161.7 (3)
C26A—O3A—C27A—C28A59.2 (7)C22B—N4B—C25B—C24B−61.9 (3)
N3A—C21A—N4C—C25C−15 (3)N5B—C24B—C25B—N4B54.8 (4)
C13A—C21A—N4C—C25C171.5 (19)C27B—O3B—C26B—O2B3.2 (6)
N3A—C21A—N4C—C22C121 (2)C27B—O3B—C26B—N5B−176.7 (3)
C13A—C21A—N4C—C22C−52 (3)C23B—N5B—C26B—O2B13.4 (5)
C21A—N4C—C22C—C23C163 (3)C24B—N5B—C26B—O2B168.3 (3)
C25C—N4C—C22C—C23C−56 (2)C23B—N5B—C26B—O3B−166.7 (3)
C26C—N5C—C23C—C22C149 (2)C24B—N5B—C26B—O3B−11.8 (5)
C24C—N5C—C23C—C22C−56 (2)C26B—O3B—C27B—C30B−57.1 (6)
N4C—C22C—C23C—N5C58 (2)C26B—O3B—C27B—C28B64.2 (5)
C26C—N5C—C24C—C25C−151 (2)C26B—O3B—C27B—C29B−178.2 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C7B—H7BA···O2Bi0.932.403.141 (2)136
Symmetry code: (i) x+1, y, z.
 

Funding information

Funding for this research was provided by: Indian Council of Medical Research (grant No. BIC/12(14)/2012 to RK); Department of Science and Technology (grant No. EMR/2014/000467 to RK; award No. SR/S2/CMP-47/2003). RK also acknowledges the Department of Science & Technology for a single-crystal X-ray diffractometer sanctioned as a National Facility under project No. SR/S2/CMP-47/2003.

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This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

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ISSN: 2414-3146
Volume 3| Part 3| March 2018| x180427
https://doi.org/10.1107/S2414314618004273
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