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

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ISSN: 2414-3146

1-(Pyridin-2-yl)-2,4-bis­­[(pyridin-2-yl)carbon­yl]-3,5-bis­(3,4,5-tri­meth­­oxy­phen­yl)cyclo­hexa­nol 2.25-hydrate

CROSSMARK_Color_square_no_text.svg

aPG and Research Department of Physics, Queen Mary's College, Chennai-4, Tamilnadu, India, bPG Department of Physics, Bhaktavatsalam Memorial College for Women, Chennai-80, Tamilnadu, India, and cDepartment of Physics, Bharathi Women's College, Chennai-108, Tamilnadu, India
*Correspondence e-mail: guqmc@yahoo.com

Edited by P. C. Healy, Griffith University, Australia (Received 28 October 2017; accepted 10 November 2017; online 21 November 2017)

In the title compound, C41H41N3O9·2.25H2O, the cyclo­hexa­nol ring adopts a chair conformation. The cyclo­hexa­nol ring makes dihedral angles of 87.89 (7) and 75.53 (8)° with the mean planes of the tri­meth­oxy­phenyl rings and dihedral angles of 84.18 (8), 85.07 (7) and 82.03 (8)° with the pyridine rings. In the crystal, the packing is stabilized by C—H⋯O, O—H⋯O and O—H⋯N hydrogen bonds involving water mol­ecules and meth­oxy O atoms, resulting in a supra­molecular network. One of the methoxy groups is disordered over two sets of sites with occupancy factors of 0.63 (3) and 0.37 (3).

3D view (loading...)
[Scheme 3D1]
Chemical scheme
[Scheme 1]

Structure description

The title compound (Fig. 1[link]) has a central cyclo­hexa­nol ring attached to two tri­meth­oxy­phenyl, one pyridine and two pyridine­carbonyl rings. The dihedral angle between the tri­meth­oxy­phenyl rings E and F is 69.65 (7)°. The cyclo­hexa­nol ring A (C39–C44) makes dihedral angles of 75.53 (8) and 87.89 (7)°, respectively, with the mean planes of the rings E (C10–C15) and F (C1–C6). The pyridine rings B (N2/C20–C24), C (N1/C25–C29) and D (N1/C25–C29) are inclined to the central cyclo­hexa­nol ring by dihedral angles of 85.07 (7), 82.03 (8) and 84.18 (8)°, respectively. The cyclo­hexa­nol ring A adopts a chair conformation with puckering parameters q2 = 0.034 (2), q3 = 0.595 (2) and QT = 0.597 (2) Å, φ2 = 288 (4) and θ2 = 3.81 (19)°, and is similar to that observed in reported structures (Çelik et al., 2016[Çelik, Í., Ersanlı, C. C., Akkurt, M., Gezegen, H. & Köseoğlu, R. (2016). Acta Cryst. E72, 976-979.]; Fun et al., 2012[Fun, H.-K., Ooi, C. W., Samshuddin, S., Narayana, B. & Sarojini, B. K. (2012). Acta Cryst. E68, o1633-o1634.]).

[Figure 1]
Figure 1
An ORTEP plot of the title compound with displacement ellipsoids drawn at the 20% probability level.

In the crystal, the mol­ecules are linked by C—H⋯O, O—H⋯O and O—H⋯N hydrogen bonds (Fig. 2[link], Table 1[link]). The trifurcated atom O10 (acting as donor to two hydrogen bonds and acceptor to one) and bifurcated atom O11 (acting as acceptor to two hydrogen bonds) of the water mol­ecules are actively involved in the formation of hydrogen bonds through carbonyl O and pyridine N atoms. The O9 atom from the hydroxyl group generates intra- and inter­molecular inter­actions with ketone atoms through O9—H9⋯O8 and O9—H9⋯O7 bonds. The packing of the mol­ecules viewed along the a axis is shown in Fig. 3[link].

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
C8—H8B⋯O3 0.96 2.40 2.918 (5) 114
C9—H9B⋯O7i 0.96 2.63 3.575 (4) 168
C11—H11⋯O8ii 0.93 2.55 3.450 (3) 163
C16—H16B⋯O12 0.96 2.16 2.951 (15) 139
C24—H24⋯O12iii 0.93 2.57 3.192 (15) 125
C27—H27⋯O4iv 0.93 2.62 3.408 (4) 143
C44—H44⋯O11v 0.98 2.56 3.464 (4) 153
O9—H9⋯O7ii 0.82 2.27 2.941 (2) 139
O9—H9⋯O8 0.82 2.17 2.760 (2) 129
O11—H11B⋯N2 0.85 (2) 2.02 (2) 2.861 (4) 169 (3)
O11—H11A⋯O10vi 0.87 (2) 1.91 (2) 2.771 (4) 171 (3)
O10—H10A⋯N3 0.86 (2) 2.00 (2) 2.857 (4) 175 (4)
O10—H10B⋯O1vi 0.86 (2) 2.16 (3) 2.939 (3) 151 (5)
Symmetry codes: (i) [-x+{\script{3\over 2}}, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]; (ii) -x+1, -y, -z+1; (iii) [-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]; (iv) [x-{\script{1\over 2}}, -y-{\script{1\over 2}}, z-{\script{1\over 2}}]; (v) [-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]; (vi) -x+1, -y, -z+2.
[Figure 2]
Figure 2
Linking of the mol­ecules and water mol­ecules by hydrogen bonds (dashed lines).
[Figure 3]
Figure 3
The crystal packing of the title compound, viewed along the a axis. Dashed lines indicate hydrogen bonds.

Synthesis and crystallization

The title compound was synthesized by the following Claisen–Schmidt reaction. In this procedure, 4-acetylpyridine­(1.5 ml, 0.01 mol) and 3,4,5-trimeth­oxybenzaldehyde (2.6 g, 0.01 mol) were dissolved in 50 ml of ethanol in a round-bottomed flask. After 15 minutes, NaOH (10%) was added and the reaction mixture was maintained at 283 K and stirred for 5 h. Then the mixture was poured onto ice. The white-coloured precipitate was collected and washed with distilled water. A colourless, diffraction-quality crystal was obtained from repeated recrystallization from ethanol solution (yield: 87%, m.p. 398 K).

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2[link]. Atom C7 and its attached H atoms are disordered over two sets of sites with occupancy factors of 0.63 (3) and 0.37 (3). Atom O12 was refined with a fixed occupancy factor of 0.25 and no H atoms attached.

Table 2
Experimental details

Crystal data
Chemical formula 4C41H41N3O9·9H2O
Mr 3039.20
Crystal system, space group Monoclinic, P21/n
Temperature (K) 293
a, b, c (Å) 15.2367 (10), 14.8923 (7), 18.8149 (9)
β (°) 111.474 (2)
V3) 3972.9 (4)
Z 1
Radiation type Mo Kα
μ (mm−1) 0.09
Crystal size (mm) 0.30 × 0.25 × 0.20
 
Data collection
Diffractometer Bruker Kappa APEXII CCD
Absorption correction Multi-scan (SADABS; Bruker, 2004[Bruker (2004). APEX2, SAINT, XPREP and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.])
Tmin, Tmax 0.972, 0.982
No. of measured, independent and observed [I > 2σ(I)] reflections 38138, 6999, 4142
Rint 0.042
(sin θ/λ)max−1) 0.595
 
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.047, 0.130, 1.08
No. of reflections 6995
No. of parameters 533
No. of restraints 13
H-atom treatment H atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3) 0.18, −0.20
Computer programs: APEX2 (Bruker, 2004[Bruker (2004). APEX2, SAINT, XPREP and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]), APEX2 and SAINT (Bruker, 2004[Bruker (2004). APEX2, SAINT, XPREP and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]), SAINT and XPREP (Bruker, 2004[Bruker (2004). APEX2, SAINT, XPREP and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]), SIR92 (Altomare et al., 1993[Altomare, A., Cascarano, G., Giacovazzo, C. & Guagliardi, A. (1993). J. Appl. Cryst. 26, 343-350.]), SHELXL2014 (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 Mercury (Macrae et al., 2008[Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.]).

Structural data


Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: APEX2 and SAINT (Bruker, 2004); data reduction: SAINT and XPREP (Bruker, 2004); program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL2014 (Sheldrick, 2015).

1-(Pyridin-2-yl)-2,4-bis[(pyridin-2-yl)carbonyl]-3,5-bis(3,4,5-trimethoxyphenyl)-cyclohexanol 2.25-hydrate top
Crystal data top
4C41H41N3O9·9H2OF(000) = 1608
Mr = 3039.20Dx = 1.270 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 15.2367 (10) ÅCell parameters from 7551 reflections
b = 14.8923 (7) Åθ = 2.5–21.9°
c = 18.8149 (9) ŵ = 0.09 mm1
β = 111.474 (2)°T = 293 K
V = 3972.9 (4) Å3Block, colourless
Z = 10.30 × 0.25 × 0.20 mm
Data collection top
Bruker Kappa APEXII CCD
diffractometer
6999 independent reflections
Radiation source: fine-focus sealed tube4142 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.042
ω and φ scanθmax = 25.0°, θmin = 2.2°
Absorption correction: multi-scan
(SADABS; Bruker, 2004)
h = 1518
Tmin = 0.972, Tmax = 0.982k = 1717
38138 measured reflectionsl = 2222
Refinement top
Refinement on F213 restraints
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.047H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.130 w = 1/[σ2(Fo2) + (0.0408P)2 + 2.0333P]
where P = (Fo2 + 2Fc2)/3
S = 1.08(Δ/σ)max < 0.001
6995 reflectionsΔρmax = 0.18 e Å3
533 parametersΔρmin = 0.20 e Å3
Special details top

Refinement. H atoms were positioned geometrically and treated as riding on their parent atoms and refined with, C—H = 0.93–0.96 Å and O—H = 0.82 Å, with Uiso(H) = 1.5 Ueq(c-methyl) and Uiso(H) = 1.2Ueq(O) for other H atoms. The water H atoms were identified through Fourier maps and fixed with their parent O atoms using DFIX 0.82 (2).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
C10.47583 (16)0.04020 (14)0.68518 (13)0.0309 (5)
C20.43319 (18)0.02820 (16)0.73806 (13)0.0393 (6)
H20.38820.01660.73080.047*
C30.4578 (2)0.08296 (18)0.80163 (14)0.0463 (7)
C40.5238 (2)0.15036 (18)0.81334 (15)0.0519 (7)
C50.5690 (2)0.15985 (17)0.76169 (16)0.0503 (7)
C60.54417 (18)0.10571 (16)0.69746 (14)0.0402 (6)
H60.57360.11350.66240.048*
C70.456 (2)0.019 (2)0.9148 (13)0.113 (7)0.37 (3)
H7A0.42120.02080.94810.170*0.37 (3)
H7B0.51990.03770.94210.170*0.37 (3)
H7C0.45630.04170.89690.170*0.37 (3)
C7'0.4051 (13)0.0152 (6)0.8755 (10)0.091 (4)0.63 (3)
H7'10.46350.04700.88720.136*0.63 (3)
H7'20.35680.04420.83370.136*0.63 (3)
H7'30.38730.01520.91950.136*0.63 (3)
C80.5355 (4)0.2949 (3)0.8708 (3)0.1271 (18)
H8A0.47570.30780.83140.191*
H8B0.58510.32030.85720.191*
H8C0.53720.32060.91810.191*
C90.7029 (3)0.2193 (3)0.7414 (2)0.0899 (12)
H9A0.73020.16030.74830.135*
H9B0.75170.26310.76290.135*
H9C0.67140.23090.68780.135*
C100.48096 (18)0.27134 (15)0.58138 (13)0.0354 (6)
C110.56584 (19)0.30086 (16)0.57766 (14)0.0424 (6)
H110.60170.26240.56020.051*
C120.5971 (2)0.38757 (17)0.59992 (15)0.0466 (7)
C130.5450 (2)0.44482 (16)0.62708 (14)0.0462 (7)
C140.4599 (2)0.41605 (17)0.62933 (14)0.0453 (7)
C150.42774 (19)0.32902 (16)0.60684 (14)0.0424 (6)
H150.37070.30990.60900.051*
C160.3273 (3)0.4507 (3)0.6625 (3)0.1220 (18)
H16A0.33830.39760.69350.183*
H16B0.30470.49780.68610.183*
H16C0.28110.43810.61290.183*
C170.5445 (3)0.5983 (2)0.6001 (2)0.0919 (13)
H17A0.47680.59690.58070.138*
H17B0.56610.65520.62400.138*
H17C0.56640.58990.55870.138*
C180.7276 (2)0.3747 (2)0.5590 (2)0.0798 (10)
H18A0.68830.36980.50600.120*
H18B0.78460.40600.56380.120*
H18C0.74290.31580.58070.120*
C190.32405 (17)0.09088 (16)0.54529 (13)0.0354 (6)
C200.28709 (19)0.14740 (16)0.59363 (14)0.0426 (7)
C210.3261 (3)0.23114 (19)0.61551 (18)0.0694 (9)
H210.37380.25240.60020.083*
C220.2919 (4)0.2829 (2)0.6613 (2)0.0973 (14)
H220.32000.33840.67810.117*
N20.2214 (3)0.2575 (3)0.68226 (19)0.0988 (12)
C230.1847 (3)0.1778 (3)0.6599 (2)0.0857 (11)
H230.13490.15930.67370.103*
C240.2162 (2)0.1203 (2)0.61726 (16)0.0599 (8)
H240.18960.06360.60450.072*
C250.21191 (18)0.05937 (15)0.44586 (13)0.0360 (6)
C260.1745 (2)0.03033 (18)0.37130 (14)0.0513 (7)
H260.21390.01600.34510.062*
C270.0774 (3)0.0226 (2)0.33555 (18)0.0712 (10)
H270.05370.00320.28510.085*
N10.01609 (19)0.04114 (19)0.36869 (16)0.0731 (8)
C280.0532 (2)0.0694 (2)0.44029 (18)0.0602 (8)
H280.01210.08320.46510.072*
C290.14823 (18)0.07962 (17)0.48042 (15)0.0457 (7)
H290.16970.10010.53060.055*
C300.57500 (18)0.12177 (15)0.68717 (13)0.0332 (6)
C310.59889 (17)0.14134 (15)0.77039 (13)0.0354 (6)
C320.67705 (19)0.10218 (18)0.82379 (14)0.0481 (7)
H320.71600.06500.80860.058*
C330.6968 (2)0.1188 (2)0.90010 (16)0.0590 (8)
H330.74980.09170.93550.071*
N30.64484 (19)0.17117 (17)0.92603 (13)0.0616 (7)
C340.5709 (2)0.2095 (2)0.87408 (17)0.0668 (9)
H340.53430.24770.89090.080*
C350.5443 (2)0.19640 (18)0.79624 (15)0.0541 (8)
H350.49080.22420.76210.065*
C390.44920 (16)0.01741 (14)0.61395 (12)0.0284 (5)
H390.48670.00270.58430.034*
C400.34386 (16)0.00810 (14)0.56285 (12)0.0294 (5)
H400.30610.02850.59220.035*
C410.31782 (16)0.06659 (14)0.48983 (12)0.0310 (5)
C420.34647 (17)0.16422 (15)0.51199 (13)0.0346 (6)
H42A0.33260.19960.46590.042*
H42B0.30900.18790.53970.042*
C430.45134 (16)0.17447 (14)0.56144 (12)0.0322 (6)
H430.48830.15010.53280.039*
C440.47249 (16)0.11756 (14)0.63428 (12)0.0302 (5)
H440.43320.13930.66190.036*
O10.41605 (17)0.07301 (15)0.85542 (12)0.0709 (6)
O20.54795 (17)0.20044 (15)0.87925 (12)0.0811 (7)
O30.63731 (17)0.22451 (15)0.77829 (13)0.0807 (7)
O40.41173 (16)0.47771 (12)0.65519 (12)0.0662 (6)
O50.58008 (15)0.52884 (11)0.65415 (11)0.0642 (6)
O60.67918 (16)0.42277 (13)0.59817 (13)0.0700 (6)
O70.63819 (12)0.10414 (11)0.66429 (9)0.0445 (4)
O80.34263 (16)0.12696 (11)0.49476 (11)0.0609 (6)
O90.36986 (11)0.04089 (10)0.44406 (8)0.0382 (4)
H90.35750.01130.43020.057*
O100.6558 (3)0.2192 (2)1.07603 (16)0.1056 (10)
O110.2246 (2)0.3390 (2)0.82088 (18)0.1155 (11)
O120.3307 (11)0.5495 (10)0.7994 (8)0.149 (5)*0.25
H11B0.219 (3)0.321 (2)0.7766 (11)0.125 (16)*
H11A0.257 (2)0.2982 (18)0.8533 (14)0.082 (13)*
H10A0.651 (3)0.202 (3)1.0309 (15)0.16 (2)*
H10B0.617 (3)0.188 (3)1.089 (2)0.16 (2)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0301 (14)0.0274 (12)0.0343 (13)0.0018 (11)0.0106 (11)0.0024 (10)
C20.0418 (16)0.0362 (14)0.0405 (14)0.0055 (12)0.0159 (12)0.0059 (11)
C30.0505 (18)0.0501 (16)0.0425 (15)0.0010 (14)0.0221 (13)0.0081 (13)
C40.0568 (19)0.0496 (17)0.0471 (16)0.0063 (15)0.0166 (15)0.0206 (14)
C50.0495 (18)0.0410 (15)0.0570 (17)0.0149 (14)0.0155 (15)0.0133 (14)
C60.0425 (16)0.0384 (14)0.0414 (14)0.0050 (12)0.0174 (12)0.0046 (12)
C70.117 (14)0.153 (17)0.076 (10)0.041 (12)0.041 (10)0.031 (12)
C7'0.120 (10)0.091 (6)0.093 (8)0.019 (5)0.078 (7)0.024 (5)
C80.176 (5)0.070 (3)0.153 (4)0.023 (3)0.081 (4)0.065 (3)
C90.080 (3)0.108 (3)0.078 (2)0.055 (2)0.024 (2)0.008 (2)
C100.0428 (16)0.0270 (13)0.0323 (13)0.0017 (12)0.0090 (11)0.0036 (10)
C110.0492 (18)0.0316 (14)0.0450 (15)0.0028 (12)0.0155 (13)0.0015 (11)
C120.0476 (18)0.0393 (15)0.0483 (16)0.0112 (14)0.0119 (14)0.0007 (13)
C130.0540 (19)0.0300 (14)0.0437 (15)0.0082 (13)0.0052 (14)0.0013 (12)
C140.0536 (19)0.0338 (14)0.0427 (15)0.0034 (14)0.0108 (13)0.0016 (12)
C150.0445 (17)0.0330 (14)0.0446 (15)0.0048 (12)0.0104 (13)0.0003 (12)
C160.114 (4)0.070 (3)0.218 (5)0.007 (3)0.103 (4)0.046 (3)
C170.098 (3)0.0373 (18)0.118 (3)0.0069 (18)0.012 (2)0.0150 (19)
C180.064 (2)0.081 (2)0.102 (3)0.0197 (19)0.040 (2)0.008 (2)
C190.0358 (15)0.0360 (14)0.0352 (14)0.0016 (11)0.0137 (12)0.0010 (11)
C200.0503 (18)0.0368 (15)0.0420 (15)0.0114 (13)0.0184 (13)0.0033 (12)
C210.097 (3)0.0397 (17)0.080 (2)0.0060 (17)0.042 (2)0.0069 (16)
C220.137 (4)0.051 (2)0.102 (3)0.016 (2)0.041 (3)0.023 (2)
N20.120 (3)0.104 (3)0.083 (2)0.040 (2)0.049 (2)0.016 (2)
C230.081 (3)0.105 (3)0.083 (3)0.031 (2)0.044 (2)0.009 (2)
C240.053 (2)0.068 (2)0.0656 (19)0.0098 (16)0.0309 (17)0.0069 (16)
C250.0397 (16)0.0300 (13)0.0355 (13)0.0021 (11)0.0103 (12)0.0025 (11)
C260.0461 (19)0.0629 (18)0.0377 (15)0.0048 (14)0.0068 (14)0.0035 (13)
C270.065 (3)0.081 (2)0.0473 (18)0.0097 (19)0.0024 (18)0.0069 (16)
N10.0465 (17)0.088 (2)0.0683 (19)0.0058 (15)0.0021 (15)0.0030 (15)
C280.0429 (19)0.069 (2)0.065 (2)0.0062 (15)0.0156 (16)0.0116 (16)
C290.0373 (17)0.0508 (16)0.0438 (15)0.0030 (13)0.0085 (13)0.0009 (13)
C300.0390 (16)0.0264 (12)0.0327 (13)0.0021 (11)0.0113 (12)0.0001 (10)
C310.0369 (15)0.0321 (13)0.0336 (13)0.0025 (11)0.0086 (12)0.0034 (11)
C320.0464 (18)0.0527 (17)0.0415 (15)0.0063 (14)0.0114 (13)0.0014 (13)
C330.061 (2)0.066 (2)0.0405 (16)0.0066 (16)0.0071 (15)0.0051 (15)
N30.0672 (19)0.0712 (17)0.0400 (14)0.0056 (15)0.0121 (13)0.0119 (13)
C340.071 (2)0.074 (2)0.0531 (19)0.0096 (18)0.0193 (18)0.0245 (17)
C350.0544 (19)0.0562 (17)0.0420 (16)0.0145 (15)0.0063 (14)0.0118 (13)
C390.0298 (14)0.0268 (12)0.0295 (12)0.0002 (10)0.0121 (10)0.0004 (10)
C400.0338 (14)0.0273 (12)0.0301 (12)0.0010 (10)0.0155 (11)0.0016 (10)
C410.0353 (15)0.0317 (13)0.0267 (12)0.0010 (11)0.0121 (11)0.0018 (10)
C420.0413 (16)0.0303 (13)0.0306 (12)0.0005 (11)0.0112 (11)0.0032 (10)
C430.0387 (15)0.0262 (12)0.0312 (12)0.0016 (11)0.0122 (11)0.0005 (10)
C440.0337 (14)0.0266 (12)0.0308 (12)0.0006 (10)0.0125 (11)0.0008 (10)
O10.0972 (18)0.0766 (15)0.0572 (13)0.0113 (13)0.0500 (13)0.0206 (12)
O20.1008 (19)0.0757 (16)0.0674 (14)0.0199 (13)0.0314 (13)0.0427 (12)
O30.0823 (17)0.0742 (15)0.0899 (16)0.0475 (13)0.0366 (14)0.0343 (13)
O40.0750 (16)0.0400 (11)0.0843 (15)0.0002 (11)0.0298 (13)0.0160 (10)
O50.0787 (15)0.0327 (10)0.0642 (13)0.0145 (10)0.0059 (11)0.0074 (9)
O60.0645 (15)0.0540 (12)0.0939 (16)0.0241 (11)0.0319 (13)0.0107 (11)
O70.0390 (11)0.0520 (11)0.0433 (10)0.0027 (9)0.0160 (9)0.0043 (8)
O80.1010 (17)0.0377 (10)0.0628 (12)0.0081 (10)0.0523 (12)0.0098 (9)
O90.0454 (11)0.0391 (9)0.0359 (9)0.0048 (8)0.0217 (8)0.0044 (7)
O100.161 (3)0.105 (2)0.0690 (18)0.051 (2)0.0637 (19)0.0157 (15)
O110.127 (3)0.152 (3)0.0771 (19)0.063 (2)0.0488 (19)0.011 (2)
Geometric parameters (Å, º) top
C1—C61.383 (3)C19—C401.517 (3)
C1—C21.385 (3)C20—C241.371 (4)
C1—C391.516 (3)C20—C211.378 (4)
C2—C31.381 (3)C21—C221.392 (5)
C2—H20.9300C21—H210.9300
C3—C41.380 (4)C22—N21.328 (5)
C3—O11.386 (3)C22—H220.9300
C4—O21.377 (3)N2—C231.314 (5)
C4—C51.389 (4)C23—C241.374 (4)
C5—O31.368 (3)C23—H230.9300
C5—C61.385 (3)C24—H240.9300
C6—H60.9300C25—C261.376 (3)
C7—O11.333 (11)C25—C291.385 (3)
C7—H7A0.9600C25—C411.524 (3)
C7—H7B0.9600C26—C271.387 (4)
C7—H7C0.9600C26—H260.9300
C7'—O11.394 (7)C27—N11.329 (4)
C7'—H7'10.9600C27—H270.9300
C7'—H7'20.9600N1—C281.324 (4)
C7'—H7'30.9600C28—C291.375 (4)
C8—O21.421 (4)C28—H280.9300
C8—H8A0.9600C29—H290.9300
C8—H8B0.9600C30—O71.218 (3)
C8—H8C0.9600C30—C311.501 (3)
C9—O31.413 (4)C30—C441.515 (3)
C9—H9A0.9600C31—C321.375 (3)
C9—H9B0.9600C31—C351.377 (3)
C9—H9C0.9600C32—C331.377 (4)
C10—C151.382 (3)C32—H320.9300
C10—C111.392 (3)C33—N31.325 (4)
C10—C431.517 (3)C33—H330.9300
C11—C121.387 (3)N3—C341.321 (4)
C11—H110.9300C34—C351.383 (4)
C12—O61.368 (3)C34—H340.9300
C12—C131.383 (4)C35—H350.9300
C13—C141.382 (4)C39—C401.546 (3)
C13—O51.383 (3)C39—C441.548 (3)
C14—O41.371 (3)C39—H390.9800
C14—C151.395 (3)C40—C411.551 (3)
C15—H150.9300C40—H400.9800
C16—O41.402 (4)C41—O91.420 (3)
C16—H16A0.9600C41—C421.531 (3)
C16—H16B0.9600C42—C431.534 (3)
C16—H16C0.9600C42—H42A0.9700
C17—O51.412 (3)C42—H42B0.9700
C17—H17A0.9600C43—C441.542 (3)
C17—H17B0.9600C43—H430.9800
C17—H17C0.9600C44—H440.9800
C18—O61.413 (4)O9—H90.8200
C18—H18A0.9600O10—H10A0.864 (18)
C18—H18B0.9600O10—H10B0.855 (19)
C18—H18C0.9600O11—H11B0.851 (18)
C19—O81.212 (3)O11—H11A0.873 (17)
C19—C201.493 (3)
C6—C1—C2119.6 (2)C21—C22—H22118.2
C6—C1—C39119.2 (2)C23—N2—C22117.3 (3)
C2—C1—C39121.2 (2)N2—C23—C24123.4 (4)
C3—C2—C1119.7 (2)N2—C23—H23118.3
C3—C2—H2120.1C24—C23—H23118.3
C1—C2—H2120.1C20—C24—C23119.4 (3)
C4—C3—C2121.2 (2)C20—C24—H24120.3
C4—C3—O1117.6 (2)C23—C24—H24120.3
C2—C3—O1121.2 (2)C26—C25—C29116.6 (2)
O2—C4—C3118.5 (3)C26—C25—C41122.5 (2)
O2—C4—C5122.5 (3)C29—C25—C41121.0 (2)
C3—C4—C5118.8 (2)C25—C26—C27119.4 (3)
O3—C5—C6123.4 (3)C25—C26—H26120.3
O3—C5—C4116.3 (2)C27—C26—H26120.3
C6—C5—C4120.3 (2)N1—C27—C26124.3 (3)
C1—C6—C5120.3 (2)N1—C27—H27117.9
C1—C6—H6119.9C26—C27—H27117.9
C5—C6—H6119.9C28—N1—C27115.6 (3)
O1—C7—H7A109.5N1—C28—C29124.4 (3)
O1—C7—H7B109.5N1—C28—H28117.8
H7A—C7—H7B109.5C29—C28—H28117.8
O1—C7—H7C109.5C28—C29—C25119.8 (3)
H7A—C7—H7C109.5C28—C29—H29120.1
H7B—C7—H7C109.5C25—C29—H29120.1
O1—C7'—H7'1109.5O7—C30—C31119.3 (2)
O1—C7'—H7'2109.5O7—C30—C44121.1 (2)
H7'1—C7'—H7'2109.5C31—C30—C44119.4 (2)
O1—C7'—H7'3109.5C32—C31—C35117.9 (2)
H7'1—C7'—H7'3109.5C32—C31—C30119.6 (2)
H7'2—C7'—H7'3109.5C35—C31—C30122.5 (2)
O2—C8—H8A109.5C31—C32—C33119.0 (3)
O2—C8—H8B109.5C31—C32—H32120.5
H8A—C8—H8B109.5C33—C32—H32120.5
O2—C8—H8C109.5N3—C33—C32123.9 (3)
H8A—C8—H8C109.5N3—C33—H33118.0
H8B—C8—H8C109.5C32—C33—H33118.0
O3—C9—H9A109.5C34—N3—C33116.4 (2)
O3—C9—H9B109.5N3—C34—C35124.2 (3)
H9A—C9—H9B109.5N3—C34—H34117.9
O3—C9—H9C109.5C35—C34—H34117.9
H9A—C9—H9C109.5C31—C35—C34118.5 (3)
H9B—C9—H9C109.5C31—C35—H35120.7
C15—C10—C11119.7 (2)C34—C35—H35120.7
C15—C10—C43121.2 (2)C1—C39—C40112.33 (18)
C11—C10—C43119.1 (2)C1—C39—C44111.33 (17)
C12—C11—C10120.1 (2)C40—C39—C44109.38 (18)
C12—C11—H11120.0C1—C39—H39107.9
C10—C11—H11120.0C40—C39—H39107.9
O6—C12—C13115.2 (2)C44—C39—H39107.9
O6—C12—C11124.4 (3)C19—C40—C39107.52 (18)
C13—C12—C11120.4 (3)C19—C40—C41112.77 (18)
C14—C13—O5120.7 (3)C39—C40—C41111.79 (18)
C14—C13—C12119.5 (2)C19—C40—H40108.2
O5—C13—C12119.8 (3)C39—C40—H40108.2
O4—C14—C13115.7 (2)C41—C40—H40108.2
O4—C14—C15123.8 (3)O9—C41—C25111.54 (18)
C13—C14—C15120.5 (3)O9—C41—C42104.72 (18)
C10—C15—C14119.8 (3)C25—C41—C42110.76 (19)
C10—C15—H15120.1O9—C41—C40111.55 (18)
C14—C15—H15120.1C25—C41—C40108.53 (18)
O4—C16—H16A109.5C42—C41—C40109.70 (17)
O4—C16—H16B109.5C41—C42—C43112.92 (19)
H16A—C16—H16B109.5C41—C42—H42A109.0
O4—C16—H16C109.5C43—C42—H42A109.0
H16A—C16—H16C109.5C41—C42—H42B109.0
H16B—C16—H16C109.5C43—C42—H42B109.0
O5—C17—H17A109.5H42A—C42—H42B107.8
O5—C17—H17B109.5C10—C43—C42113.21 (19)
H17A—C17—H17B109.5C10—C43—C44110.89 (18)
O5—C17—H17C109.5C42—C43—C44108.46 (18)
H17A—C17—H17C109.5C10—C43—H43108.0
H17B—C17—H17C109.5C42—C43—H43108.0
O6—C18—H18A109.5C44—C43—H43108.0
O6—C18—H18B109.5C30—C44—C43113.00 (19)
H18A—C18—H18B109.5C30—C44—C39106.86 (18)
O6—C18—H18C109.5C43—C44—C39110.83 (17)
H18A—C18—H18C109.5C30—C44—H44108.7
H18B—C18—H18C109.5C43—C44—H44108.7
O8—C19—C20118.5 (2)C39—C44—H44108.7
O8—C19—C40121.1 (2)C7—O1—C3119.0 (8)
C20—C19—C40120.3 (2)C3—O1—C7'115.6 (4)
C24—C20—C21118.3 (3)C4—O2—C8117.1 (3)
C24—C20—C19123.4 (2)C5—O3—C9117.7 (2)
C21—C20—C19118.3 (3)C14—O4—C16118.2 (2)
C20—C21—C22117.9 (4)C13—O5—C17113.7 (2)
C20—C21—H21121.0C12—O6—C18118.4 (2)
C22—C21—H21121.0C41—O9—H9109.5
N2—C22—C21123.6 (4)H10A—O10—H10B107 (3)
N2—C22—H22118.2H11B—O11—H11A107 (2)
C6—C1—C2—C31.4 (4)C30—C31—C35—C34179.0 (3)
C39—C1—C2—C3178.8 (2)N3—C34—C35—C311.3 (5)
C1—C2—C3—C40.6 (4)C6—C1—C39—C40119.8 (2)
C1—C2—C3—O1179.6 (2)C2—C1—C39—C4060.3 (3)
C2—C3—C4—O2177.6 (3)C6—C1—C39—C44117.1 (2)
O1—C3—C4—O23.4 (4)C2—C1—C39—C4462.8 (3)
C2—C3—C4—C53.0 (4)O8—C19—C40—C3981.9 (3)
O1—C3—C4—C5177.9 (3)C20—C19—C40—C3994.0 (3)
O2—C4—C5—O32.3 (4)O8—C19—C40—C4141.8 (3)
C3—C4—C5—O3176.6 (3)C20—C19—C40—C41142.3 (2)
O2—C4—C5—C6177.8 (3)C1—C39—C40—C1955.1 (2)
C3—C4—C5—C63.5 (4)C44—C39—C40—C19179.28 (18)
C2—C1—C6—C50.9 (4)C1—C39—C40—C41179.42 (18)
C39—C1—C6—C5179.3 (2)C44—C39—C40—C4156.4 (2)
O3—C5—C6—C1178.5 (3)C26—C25—C41—O90.6 (3)
C4—C5—C6—C11.6 (4)C29—C25—C41—O9178.7 (2)
C15—C10—C11—C120.4 (4)C26—C25—C41—C42116.8 (2)
C43—C10—C11—C12176.2 (2)C29—C25—C41—C4265.1 (3)
C10—C11—C12—O6179.8 (2)C26—C25—C41—C40122.7 (2)
C10—C11—C12—C131.0 (4)C29—C25—C41—C4055.4 (3)
O6—C12—C13—C14178.5 (2)C19—C40—C41—O960.3 (2)
C11—C12—C13—C142.3 (4)C39—C40—C41—O961.0 (2)
O6—C12—C13—O53.8 (4)C19—C40—C41—C2563.0 (2)
C11—C12—C13—O5175.4 (2)C39—C40—C41—C25175.68 (18)
O5—C13—C14—O43.9 (4)C19—C40—C41—C42175.8 (2)
C12—C13—C14—O4178.4 (2)C39—C40—C41—C4254.5 (2)
O5—C13—C14—C15175.6 (2)O9—C41—C42—C4363.8 (2)
C12—C13—C14—C152.1 (4)C25—C41—C42—C43175.82 (19)
C11—C10—C15—C140.6 (4)C40—C41—C42—C4356.0 (3)
C43—C10—C15—C14175.9 (2)C15—C10—C43—C4246.1 (3)
O4—C14—C15—C10179.9 (2)C11—C10—C43—C42137.3 (2)
C13—C14—C15—C100.6 (4)C15—C10—C43—C4476.0 (3)
O8—C19—C20—C24139.8 (3)C11—C10—C43—C44100.6 (2)
C40—C19—C20—C2444.3 (4)C41—C42—C43—C10178.05 (19)
O8—C19—C20—C2140.1 (4)C41—C42—C43—C4458.4 (2)
C40—C19—C20—C21135.9 (3)O7—C30—C44—C4354.1 (3)
C24—C20—C21—C220.8 (4)C31—C30—C44—C43130.5 (2)
C19—C20—C21—C22179.3 (3)O7—C30—C44—C3968.1 (3)
C20—C21—C22—N22.8 (6)C31—C30—C44—C39107.3 (2)
C21—C22—N2—C232.1 (6)C10—C43—C44—C3055.8 (3)
C22—N2—C23—C240.6 (6)C42—C43—C44—C30179.26 (18)
C21—C20—C24—C231.7 (4)C10—C43—C44—C39175.7 (2)
C19—C20—C24—C23178.2 (3)C42—C43—C44—C3959.4 (2)
N2—C23—C24—C202.5 (5)C1—C39—C44—C3052.7 (2)
C29—C25—C26—C270.3 (4)C40—C39—C44—C30177.41 (18)
C41—C25—C26—C27177.9 (2)C1—C39—C44—C43176.18 (19)
C25—C26—C27—N10.4 (5)C40—C39—C44—C4359.1 (2)
C26—C27—N1—C280.7 (5)C4—C3—O1—C790 (2)
C27—N1—C28—C290.3 (5)C2—C3—O1—C791 (2)
N1—C28—C29—C250.4 (4)C4—C3—O1—C7'138.1 (10)
C26—C25—C29—C280.6 (4)C2—C3—O1—C7'42.8 (10)
C41—C25—C29—C28177.6 (2)C3—C4—O2—C8122.9 (3)
O7—C30—C31—C3229.5 (3)C5—C4—O2—C862.8 (4)
C44—C30—C31—C32146.1 (2)C6—C5—O3—C918.4 (4)
O7—C30—C31—C35151.7 (3)C4—C5—O3—C9161.7 (3)
C44—C30—C31—C3532.8 (3)C13—C14—O4—C16176.7 (3)
C35—C31—C32—C330.6 (4)C15—C14—O4—C162.8 (4)
C30—C31—C32—C33178.3 (2)C14—C13—O5—C1784.7 (3)
C31—C32—C33—N30.2 (4)C12—C13—O5—C1797.6 (3)
C32—C33—N3—C340.9 (5)C13—C12—O6—C18169.1 (3)
C33—N3—C34—C351.6 (5)C11—C12—O6—C1811.8 (4)
C32—C31—C35—C340.1 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C8—H8B···O30.962.402.918 (5)114
C9—H9B···O7i0.962.633.575 (4)168
C11—H11···O8ii0.932.553.450 (3)163
C16—H16B···O120.962.162.951 (15)139
C24—H24···O12iii0.932.573.192 (15)125
C27—H27···O4iv0.932.623.408 (4)143
C44—H44···O11v0.982.563.464 (4)153
O9—H9···O7ii0.822.272.941 (2)139
O9—H9···O80.822.172.760 (2)129
O11—H11B···N20.85 (2)2.02 (2)2.861 (4)169 (3)
O11—H11A···O10vi0.87 (2)1.91 (2)2.771 (4)171 (3)
O10—H10A···N30.86 (2)2.00 (2)2.857 (4)175 (4)
O10—H10B···O1vi0.86 (2)2.16 (3)2.939 (3)151 (5)
Symmetry codes: (i) x+3/2, y+1/2, z+3/2; (ii) x+1, y, z+1; (iii) x+1/2, y+1/2, z+3/2; (iv) x1/2, y1/2, z1/2; (v) x+1/2, y1/2, z+3/2; (vi) x+1, y, z+2.
 

Acknowledgements

The authors thank the Central Instrumentation Facility (DST–FIST), Queen Mary's College, Chennai-4, for computing facilities and SAIF, IIT, Madras, for the X-ray data collection facilities.

References

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First citationFun, H.-K., Ooi, C. W., Samshuddin, S., Narayana, B. & Sarojini, B. K. (2012). Acta Cryst. E68, o1633–o1634.  CSD CrossRef CAS IUCr Journals Google Scholar
First citationMacrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466–470.  Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
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