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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 6| Part 2| February 2021| x210057
https://doi.org/10.1107/S2414314621000572

Di­methyl 3,3′-[(4-nitro­phen­yl)methyl­ene]bis­­(1H-indole-2-carboxyl­ate) ethanol hemisolvate

CROSSMARK_Color_square_no_text.svg
Yu-Long Li,a Jin Zhou,a,b Hong Jiang,a Hong-Shun Sun,a* Rui-Zhe Li,a Sha-Li Liua and Xu-Dong Zhanga

aTargeted MRI Contrast Agents Laboratory of Jiangsu Province, Nanjing Polytechnic Institute, Nanjing 210048, People's Republic of China, and bCollege of Chemistry and Molecular Engineering, Nanjing Tech University, Nanjing 211816, People's Republic of China
*Correspondence e-mail: njutshs@126.com

Edited by D.-J. Xu, Zhejiang University (Yuquan Campus), China (Received 6 January 2021; accepted 15 January 2021; online 26 January 2021)

There are two main molecules in asymmetric unit of the title compound, C27H21N3O6·0.5C2H5OH. In both, the indole ring systems are approximately perpendicular to each other, at dihedral angles of 69.3 (5) and 82.8(4)°. In the crystal, mol­ecules are linked by N—H⋯O and O—H⋯O hydrogen bonds into a three-dimensional supra­molecular architecture. The solvent ethanol mol­ecule acts as a donor, forming an O—H⋯O hydrogen bond, reinforcing the structure.

CCDC reference: 2056440

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

Structure description

There are abundant bis­(indol­yl)methane derivatives in various terrestrial and marine natural resources (Sundberg, 1996[Sundberg, R. J. (1996). The Chemistry of Indoles, p. 113 New York: Academic Press.]). They can be used as precursors for MRI necrosis avid contrast agents (Ni, 2008[Ni, Y.-C. (2008). Curr. Med. Imaging Rev. 4, 96-112.]). As part of our ongoing studies of bis­(indo­yl)methane compounds, we now report the synthesis and crystal structure of the title bis­(indoly)methane compound.

The mol­ecular structure of the title compound is shown in Fig. 1[link]. In the first bisindole molhe two indole ring systems are nearly perpendicular to one another [dihedral angle = 69.3 (5)°] while the benzene ring (C2–C7) is twisted to the N2/C8–C15 and N3/C18–C25 indole ring systems by dihedral angles of 44.3 (3) and 77.6 (4)°, respectively. The carboxyl groups are approximately co-planar with the attached indole ring systems, the dihedral angles between the carboxyl groups and the mean plane of the N2/C8–C15 and N3/C18–C25 indole ring systems being 20.7 (4) and 3.8 (5)°, respectively. For the second bisindole molecule, the two indole ring systems are also nearly perpendicular to one another [dihedral angle = 82.8 (4)°] while the benzene ring (C29–C34) is twisted to the N5/C35–C42 and N6/C45–C52 indole ring systems with dihedral angles of 88.5 (5) and 81.8 (4)°, respectively.

[Figure 1]
Figure 1
The mol­ecular structure of the title mol­ecule with the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level.

In the crystal, mol­ecules are linked by N—H⋯O and O—H⋯O hydrogen bonds into a three-dimensional supra­molecular architecture. The solvent ethanol mol­ecule acts as a donor, forming an O—H⋯O hydrogen bond, reinforcing the structure (Table 1[link], Fig. 2[link]).

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
N2—H2A⋯O13i 0.86 2.00 2.814 (7) 157
N3—H3A⋯O4ii 0.86 2.05 2.892 (6) 166
N5—H5A⋯O12iii 0.86 2.01 2.848 (6) 163
N6—H6B⋯O10iv 0.86 2.16 2.984 (6) 160
O13—H13B⋯O5 0.82 1.91 2.733 (7) 177
Symmetry codes: (i) x, y+1, z; (ii) [-x+2, -y+1, -z]; (iii) [-x+1, -y+1, -z+1]; (iv) [x, y-1, z].
[Figure 2]
Figure 2
A packing diagram of the title compound. Hydrogen bonds are shown as dashed lines.

Several similar structures have been reported previously, viz. diethyl 3,3′-(phenyl­methyl­ene)bis­(1H-indole-2-carboxyl­ate) (Sun et al., 2012[Sun, H.-S., Li, Y.-L., Xu, N., Xu, H. & Zhang, J.-D. (2012). Acta Cryst. E68, o2764.]), dimethyl 3,3′-[(3-nitro­phen­yl)methyl­ene]bis­(1H-indole-2-carboxyl­ate) ethanol monosolvate (Sun et al., 2014[Sun, H.-S., Li, Y.-L., Jiang, H., Xu, N. & Xu, H. (2014). Acta Cryst. E70, 370-372.]), diethyl 3,3′-[(4-nitro­phen­yl)methyl­ene]bis­(1H-indole-2-carb­oxyl­ate) (Sun et al., 2017[Sun, H.-S., Li, Y.-L., Jiang, H., Chen, Y.-L. & Hu, Y.-D. (2017). Acta Cryst. E73, 1956-1958.]) and diethyl 3,3′-[(3-fluoro­phen­yl)methyl­ene]bis­(1H-indole-2-carboxyl­ate) (Jiang et al., 2020[Jiang, H., Li, Y.-L., Zhou, J., Sun, H.-S., Zhang, Q.-Y., Shi, X.-H., Zhang, Z.-Y. & Ling, T. (2020). IUCrData, 5, x200912.]). In these structures, the indole ring systems are also nearly perpendicular to one another, making dihedral angles of 82.0 (5), 89.3 (5), 89.7 (5) and 88.3 (4)°, respectively.

Synthesis and crystallization

Methyl indole-2-carboxyl­ate (1.75 g, 10 mmol) was dissolved in 20 ml of ethanol, and 4-nitro­benzaldehyde (0.76 g, 5 mmol) and concentrated HCl (0.5 ml) were added and the mixture was heated to reflux temperature for 2 h. After cooling, the white product was filtered off and washed thoroughly with ethanol. The reaction was monitored by TLC (AcOEt: hexane = 1:3). Yield 90%. Single crystals of the title compound suitable for X-ray analysis were obtained by slow evaporation of an ethanol solution.

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2[link].

Table 2
Experimental details

Crystal data
Chemical formula 2C27H21N3O6·C2H6O
Mr 1013.00
Crystal system, space group Monoclinic, P21/c
Temperature (K) 293
a, b, c (Å) 18.248 (4), 10.304 (2), 27.541 (6)
β (°) 101.41 (3)
V (Å3) 5076.1 (18)
Z 4
Radiation type Mo Kα
μ (mm−1) 0.10
Crystal size (mm) 0.20 × 0.20 × 0.10
 
Data collection
Diffractometer Enraf–Nonius CAD-4
Absorption correction ψ scan (North et al., 1968[North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351-359.])
Tmin, Tmax 0.97, 0.98
No. of measured, independent and observed [I > 2σ(I)] reflections 9324, 9324, 4039
Rint 0.160
(sin θ/λ)max (Å−1) 0.603
 
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.104, 0.213, 1.20
No. of reflections 9324
No. of parameters 676
No. of restraints 2
H-atom treatment H-atom parameters constrained
Δρmax, Δρmin (e Å−3) 0.36, −0.28
Computer programs: CAD-4 EXPRESS (Enraf–Nonius, 1994[Enraf-Nonius (1994). CAD-4 EXPRESS. Enraf-Nonius, Delft, The Netherlands.]), XCAD4 (Harms & Wocadlo, 1995[Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany.]) and SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]).

Structural data

CCDC reference: 2056440

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2414314621000572/xu4043sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314621000572/xu4043Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2414314621000572/xu4043Isup3.cml

checkCIF report


Computing details top

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994); cell refinement: CAD-4 EXPRESS (Enraf–Nonius, 1994); data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Dimethyl 3,3'-[(4-nitrophenyl)methylene]bis(1H-indole-2-carboxylate) ethanol hemisolvate top
Crystal data top
2C27H21N3O6·C2H6OF(000) = 2120
Mr = 1013.00Dx = 1.326 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 18.248 (4) ÅCell parameters from 25 reflections
b = 10.304 (2) Åθ = 9–12°
c = 27.541 (6) ŵ = 0.10 mm−1
β = 101.41 (3)°T = 293 K
V = 5076.1 (18) Å3Block, colorless
Z = 40.20 × 0.20 × 0.10 mm
Data collection top
Enraf–Nonius CAD-4
diffractometer		9324 independent reflections
Radiation source: fine-focus sealed tube4039 reflections with I > 2σ(I)
Detector resolution: 28.5714 pixels mm-1Rint = 0.160
ω scansθmax = 25.4°, θmin = 1.1°
Absorption correction: ψ scan
(North et al., 1968)		h = 0→22
Tmin = 0.97, Tmax = 0.98k = 0→12
9324 measured reflectionsl = −33→32
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.104Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.213H-atom parameters constrained
S = 1.20 w = 1/[σ2(Fo2) + (0.050P)2 + 2.P]
where P = (Fo2 + 2Fc2)/3
9324 reflections(Δ/σ)max < 0.001
676 parametersΔρmax = 0.36 e Å−3
2 restraintsΔρmin = −0.28 e Å−3
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. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > 2sigma(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
N20.9831 (3)0.9393 (4)0.14010 (17)0.0539 (13)
H2A1.01271.00460.14110.065*
C10.9320 (3)0.5961 (5)0.11280 (19)0.0408 (14)
H1A0.98370.56460.11900.049*
N10.7905 (4)0.3205 (6)0.2503 (2)0.0752 (17)
O10.8245 (4)0.3088 (7)0.2916 (2)0.147 (3)
C20.8937 (3)0.5178 (5)0.1471 (2)0.0406 (13)
O20.7277 (3)0.2809 (5)0.23639 (18)0.0842 (15)
O31.1030 (2)0.8945 (4)0.10153 (16)0.0692 (13)
N30.8863 (2)0.4737 (4)−0.01617 (16)0.0488 (12)
H3A0.89030.4179−0.03870.059*
C30.9289 (3)0.5036 (6)0.1954 (2)0.0576 (16)
H3B0.97620.53960.20550.069*
N40.6521 (4)0.5750 (8)0.2207 (3)0.092 (2)
O41.0854 (2)0.6789 (4)0.09867 (14)0.0573 (11)
C40.8975 (4)0.4384 (6)0.2296 (2)0.0641 (18)
H4A0.92270.42960.26230.077*
O50.9967 (2)0.3403 (4)0.09448 (16)0.0741 (14)
C50.8273 (4)0.3867 (6)0.2139 (2)0.0556 (17)
N50.5897 (2)0.5494 (4)0.49143 (17)0.0487 (12)
H5A0.58500.61780.50850.058*
O60.9745 (2)0.2731 (3)0.01570 (14)0.0635 (12)
C60.7899 (3)0.3955 (5)0.1665 (2)0.0551 (17)
H6A0.74250.35950.15670.066*
N60.5217 (3)−0.0105 (4)0.39919 (18)0.0523 (13)
H6B0.5035−0.07590.41220.063*
O70.7097 (4)0.6377 (6)0.2306 (2)0.124 (2)
C70.8245 (3)0.4602 (6)0.1328 (2)0.0568 (16)
H7A0.80040.46470.09980.068*
O80.6225 (3)0.5476 (8)0.1784 (2)0.158 (3)
C80.9376 (3)0.7386 (5)0.12664 (18)0.0400 (13)
C90.8841 (3)0.8163 (5)0.14583 (18)0.0410 (14)
O90.4550 (2)0.5844 (4)0.37946 (17)0.0687 (13)
O100.4921 (2)0.7300 (4)0.43938 (17)0.0739 (13)
C100.8120 (3)0.7974 (6)0.1546 (2)0.0534 (16)
H10A0.78930.71650.14910.064*
C110.7748 (3)0.8978 (6)0.1714 (2)0.0627 (18)
H11A0.72690.88470.17730.075*
O110.4208 (2)0.0506 (4)0.45411 (17)0.0748 (14)
C120.8081 (4)1.0198 (6)0.1798 (2)0.071 (2)
H12A0.78211.08680.19150.085*
O120.4222 (2)0.2619 (4)0.43498 (14)0.0587 (11)
C130.8771 (4)1.0426 (6)0.1712 (2)0.0601 (18)
H13A0.89901.12400.17710.072*
O131.0623 (4)0.1713 (5)0.1666 (2)0.146 (3)
H13B1.04360.22400.14540.219*
C140.9146 (3)0.9412 (5)0.1535 (2)0.0476 (15)
C150.9967 (3)0.8174 (5)0.12499 (19)0.0434 (14)
C161.0642 (3)0.7862 (6)0.1073 (2)0.0462 (15)
C171.1726 (3)0.8759 (7)0.0856 (3)0.096 (3)
H17A1.19560.95860.08270.144*
H17B1.20530.82360.10940.144*
H17C1.16350.83310.05400.144*
C180.9023 (3)0.5722 (5)0.05790 (18)0.0379 (13)
C190.8530 (3)0.6490 (5)0.02260 (19)0.0415 (14)
C200.8157 (3)0.7670 (5)0.0226 (2)0.0546 (16)
H20A0.82000.81400.05190.066*
C210.7729 (3)0.8144 (6)−0.0200 (2)0.0617 (18)
H21A0.74880.8937−0.01940.074*
C220.7647 (3)0.7462 (6)−0.0643 (2)0.0653 (18)
H22A0.73480.7804−0.09270.078*
C230.8000 (3)0.6288 (6)−0.0669 (2)0.0634 (18)
H23A0.79400.5819−0.09630.076*
C240.8455 (3)0.5837 (5)−0.0231 (2)0.0448 (14)
C250.9202 (3)0.4655 (5)0.0326 (2)0.0436 (14)
C260.9679 (3)0.3557 (5)0.0517 (2)0.0478 (15)
C271.0198 (4)0.1602 (5)0.0313 (2)0.076 (2)
H27A1.02150.10640.00310.115*
H27B1.06960.18700.04620.115*
H27C0.99850.11210.05500.115*
C280.5378 (3)0.3441 (5)0.3791 (2)0.0435 (14)
H28A0.48410.36320.37250.052*
C290.5678 (3)0.4072 (5)0.3375 (2)0.0425 (14)
C300.5284 (3)0.4046 (6)0.2900 (2)0.0698 (19)
H30A0.48210.36360.28350.084*
C310.5543 (4)0.4603 (8)0.2512 (2)0.081 (2)
H31A0.52620.45760.21910.097*
C320.6227 (4)0.5199 (6)0.2613 (2)0.0579 (17)
C330.6644 (3)0.5235 (5)0.3077 (2)0.0572 (17)
H33A0.71130.56240.31380.069*
C340.6364 (3)0.4690 (5)0.3455 (2)0.0550 (16)
H34A0.66440.47360.37760.066*
C350.5697 (3)0.4046 (5)0.4289 (2)0.0424 (14)
C360.6299 (3)0.3608 (5)0.4667 (2)0.0402 (13)
C370.6785 (3)0.2536 (6)0.4714 (2)0.0560 (16)
H37A0.67310.19100.44670.067*
C380.7334 (3)0.2426 (6)0.5125 (2)0.0635 (17)
H38A0.76630.17300.51480.076*
C390.7419 (3)0.3308 (6)0.5509 (2)0.0626 (18)
H39A0.77920.31820.57890.075*
C400.6954 (3)0.4379 (6)0.5482 (2)0.0607 (17)
H40A0.70100.49820.57380.073*
C410.6397 (3)0.4520 (5)0.5056 (2)0.0483 (15)
C420.5479 (3)0.5207 (5)0.4455 (2)0.0465 (14)
C430.4962 (3)0.6238 (6)0.4224 (2)0.0506 (15)
C440.4048 (4)0.6789 (6)0.3526 (3)0.089 (2)
H44A0.37790.64090.32240.134*
H44B0.37010.70670.37250.134*
H44C0.43290.75220.34490.134*
C450.5442 (3)0.1959 (5)0.3796 (2)0.0434 (14)
C460.5886 (3)0.1132 (5)0.3559 (2)0.0469 (15)
C470.6385 (3)0.1274 (6)0.3240 (2)0.0561 (17)
H47A0.65130.20980.31470.067*
C480.6686 (4)0.0199 (7)0.3062 (3)0.073 (2)
H48A0.70190.03020.28490.088*
C490.6505 (4)−0.1041 (6)0.3196 (2)0.0636 (19)
H49A0.6721−0.17520.30710.076*
C500.6018 (3)−0.1247 (6)0.3504 (2)0.0596 (17)
H50A0.5888−0.20810.35840.072*
C510.5727 (3)−0.0167 (5)0.3692 (2)0.0455 (15)
C520.5040 (3)0.1183 (5)0.4053 (2)0.0475 (15)
C530.4451 (3)0.1516 (6)0.4333 (2)0.0460 (15)
C540.3624 (4)0.0783 (6)0.4808 (3)0.084 (2)
H54A0.3478−0.00050.49490.126*
H54B0.38040.13930.50680.126*
H54C0.32020.11440.45860.126*
C551.1147 (7)0.2243 (9)0.1965 (4)0.226 (8)
H55A1.15950.17740.19300.271*
H55B1.10600.20290.22920.271*
C561.1354 (5)0.3581 (9)0.1991 (4)0.151 (4)
H56A1.17760.37080.22560.227*
H56B1.14840.38380.16830.227*
H56C1.09420.40960.20490.227*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N20.070 (4)0.031 (3)0.059 (3)−0.009 (3)0.007 (3)−0.009 (2)
C10.042 (3)0.035 (3)0.045 (3)0.004 (3)0.007 (3)−0.010 (3)
N10.098 (5)0.071 (4)0.058 (4)−0.008 (4)0.018 (4)−0.002 (3)
O10.152 (6)0.222 (8)0.063 (4)−0.065 (5)0.013 (4)0.040 (5)
C20.048 (4)0.030 (3)0.041 (3)0.000 (3)0.004 (3)−0.004 (3)
O20.097 (4)0.074 (3)0.091 (4)−0.020 (3)0.041 (3)−0.009 (3)
O30.056 (3)0.062 (3)0.093 (4)−0.017 (2)0.024 (3)0.003 (3)
N30.071 (3)0.037 (3)0.036 (3)0.001 (3)0.005 (2)−0.002 (2)
C30.054 (4)0.068 (4)0.047 (4)−0.012 (3)0.001 (3)0.007 (3)
N40.079 (5)0.134 (6)0.064 (4)0.005 (4)0.016 (4)0.029 (5)
O40.063 (3)0.051 (3)0.062 (3)−0.002 (2)0.023 (2)−0.011 (2)
C40.081 (5)0.073 (4)0.033 (4)−0.014 (4)−0.001 (3)0.010 (3)
O50.107 (4)0.050 (3)0.054 (3)0.028 (3)−0.011 (3)−0.005 (2)
C50.070 (5)0.046 (4)0.059 (5)−0.006 (3)0.033 (4)−0.002 (3)
N50.061 (3)0.028 (3)0.057 (3)−0.006 (2)0.014 (3)−0.011 (2)
O60.093 (3)0.033 (2)0.060 (3)0.013 (2)0.004 (2)−0.008 (2)
C60.062 (4)0.053 (4)0.047 (4)−0.018 (3)0.005 (3)−0.012 (3)
N60.062 (3)0.021 (2)0.072 (4)0.001 (2)0.009 (3)0.000 (2)
O70.154 (6)0.131 (5)0.099 (5)−0.043 (5)0.055 (4)0.009 (4)
C70.059 (4)0.064 (4)0.046 (4)−0.008 (3)0.005 (3)−0.002 (3)
O80.111 (5)0.280 (9)0.076 (4)−0.012 (5)0.002 (4)0.062 (5)
C80.047 (4)0.032 (3)0.041 (3)−0.001 (3)0.008 (3)−0.001 (3)
C90.057 (4)0.034 (3)0.032 (3)−0.001 (3)0.008 (3)−0.002 (3)
O90.067 (3)0.043 (2)0.089 (4)0.019 (2)−0.002 (3)0.009 (2)
O100.094 (4)0.028 (2)0.100 (4)0.004 (2)0.020 (3)−0.005 (2)
C100.056 (4)0.044 (4)0.061 (4)−0.003 (3)0.014 (3)−0.011 (3)
C110.057 (4)0.062 (4)0.070 (5)0.022 (4)0.015 (4)0.008 (4)
O110.075 (3)0.049 (3)0.109 (4)−0.011 (2)0.040 (3)0.017 (3)
C120.079 (5)0.054 (4)0.084 (5)0.019 (4)0.025 (4)−0.005 (4)
O120.069 (3)0.040 (2)0.072 (3)0.004 (2)0.025 (2)−0.005 (2)
C130.074 (5)0.036 (3)0.071 (5)0.009 (3)0.017 (4)−0.005 (3)
O130.187 (6)0.069 (4)0.136 (5)−0.052 (4)−0.079 (5)0.024 (4)
C140.053 (4)0.046 (4)0.045 (4)0.004 (3)0.013 (3)−0.005 (3)
C150.051 (4)0.039 (3)0.039 (3)−0.009 (3)0.006 (3)−0.004 (3)
C160.041 (4)0.053 (4)0.042 (3)−0.012 (3)0.003 (3)−0.007 (3)
C170.054 (5)0.104 (6)0.138 (7)−0.024 (4)0.037 (5)−0.002 (5)
C180.039 (3)0.039 (3)0.036 (3)−0.009 (3)0.006 (3)0.000 (3)
C190.049 (4)0.038 (3)0.038 (3)−0.004 (3)0.009 (3)−0.005 (3)
C200.063 (4)0.046 (4)0.055 (4)0.006 (3)0.012 (3)0.001 (3)
C210.071 (5)0.058 (4)0.054 (4)0.019 (3)0.009 (4)0.004 (4)
C220.081 (5)0.062 (4)0.044 (4)0.020 (4)−0.010 (3)0.009 (3)
C230.069 (4)0.062 (4)0.057 (4)0.003 (4)0.005 (3)0.000 (4)
C240.056 (4)0.038 (3)0.040 (4)0.005 (3)0.009 (3)0.004 (3)
C250.056 (4)0.029 (3)0.047 (4)−0.003 (3)0.014 (3)−0.002 (3)
C260.053 (4)0.036 (3)0.056 (4)0.001 (3)0.015 (3)−0.009 (3)
C270.109 (6)0.042 (4)0.079 (5)0.021 (4)0.021 (4)0.007 (4)
C280.039 (3)0.033 (3)0.057 (4)−0.003 (3)0.005 (3)−0.006 (3)
C290.039 (3)0.030 (3)0.057 (4)0.004 (3)0.005 (3)0.005 (3)
C300.053 (4)0.082 (5)0.067 (5)−0.018 (4)−0.007 (4)0.007 (4)
C310.066 (5)0.128 (7)0.043 (4)−0.006 (5)−0.002 (4)0.015 (4)
C320.066 (5)0.057 (4)0.051 (4)0.009 (4)0.013 (4)0.017 (3)
C330.059 (4)0.047 (4)0.064 (5)−0.005 (3)0.009 (4)−0.005 (3)
C340.058 (4)0.052 (4)0.053 (4)−0.004 (3)0.005 (3)−0.004 (3)
C350.039 (3)0.028 (3)0.061 (4)−0.002 (3)0.012 (3)0.001 (3)
C360.044 (3)0.026 (3)0.050 (4)−0.004 (3)0.007 (3)0.005 (3)
C370.051 (4)0.055 (4)0.059 (4)−0.003 (3)0.005 (3)0.002 (3)
C380.070 (5)0.056 (4)0.059 (4)0.006 (4)−0.001 (4)0.001 (4)
C390.065 (4)0.057 (4)0.062 (5)−0.003 (4)0.002 (3)0.013 (4)
C400.075 (5)0.055 (4)0.049 (4)−0.022 (4)0.005 (3)0.001 (3)
C410.057 (4)0.037 (3)0.052 (4)−0.009 (3)0.014 (3)0.002 (3)
C420.040 (3)0.041 (3)0.057 (4)−0.004 (3)0.006 (3)0.006 (3)
C430.045 (4)0.042 (4)0.068 (5)−0.004 (3)0.016 (3)0.006 (3)
C440.071 (5)0.060 (4)0.129 (7)0.013 (4)0.000 (5)0.013 (5)
C450.038 (3)0.029 (3)0.058 (4)−0.009 (3)−0.002 (3)−0.002 (3)
C460.047 (4)0.031 (3)0.061 (4)0.001 (3)0.007 (3)−0.011 (3)
C470.056 (4)0.041 (4)0.074 (5)0.006 (3)0.020 (4)−0.005 (3)
C480.068 (5)0.073 (5)0.085 (5)0.009 (4)0.031 (4)−0.009 (4)
C490.074 (5)0.034 (4)0.080 (5)0.013 (3)0.007 (4)−0.010 (3)
C500.057 (4)0.040 (4)0.084 (5)0.002 (3)0.019 (4)−0.005 (3)
C510.040 (3)0.034 (3)0.062 (4)0.005 (3)0.011 (3)−0.013 (3)
C520.050 (4)0.032 (3)0.058 (4)−0.006 (3)0.004 (3)−0.003 (3)
C530.042 (4)0.045 (4)0.049 (4)−0.006 (3)0.005 (3)−0.011 (3)
C540.084 (5)0.072 (5)0.113 (6)−0.009 (4)0.060 (5)0.010 (4)
C550.255 (14)0.116 (9)0.228 (14)−0.099 (9)−0.142 (11)0.105 (9)
C560.115 (8)0.165 (10)0.157 (10)−0.038 (7)−0.013 (7)−0.020 (8)
Geometric parameters (Å, º) top
N2—C151.362 (6)C19—C241.410 (7)
N2—C141.371 (6)C20—C211.364 (7)
N2—H2A0.8600C20—H20A0.9300
C1—C81.516 (7)C21—C221.391 (8)
C1—C21.515 (7)C21—H21A0.9300
C1—C181.522 (7)C22—C231.380 (8)
C1—H1A0.9800C22—H22A0.9300
N1—O11.189 (7)C23—C241.402 (7)
N1—O21.205 (6)C23—H23A0.9300
N1—C51.479 (8)C25—C261.461 (7)
C2—C31.366 (7)C27—H27A0.9600
C2—C71.380 (7)C27—H27B0.9600
O3—C161.349 (6)C27—H27C0.9600
O3—C171.436 (6)C28—C291.509 (7)
N3—C241.349 (6)C28—C351.517 (7)
N3—C251.365 (6)C28—C451.531 (7)
N3—H3A0.8600C28—H28A0.9800
C3—C41.372 (7)C29—C301.364 (7)
C3—H3B0.9300C29—C341.383 (7)
N4—O81.217 (8)C30—C311.376 (8)
N4—O71.217 (7)C30—H30A0.9300
N4—C321.449 (8)C31—C321.368 (8)
O4—C161.211 (6)C31—H31A0.9300
C4—C51.375 (7)C32—C331.353 (8)
C4—H4A0.9300C33—C341.368 (7)
O5—C261.202 (6)C33—H33A0.9300
C5—C61.352 (8)C34—H34A0.9300
N5—C411.360 (6)C35—C421.367 (7)
N5—C421.375 (6)C35—C361.429 (7)
N5—H5A0.8600C36—C371.406 (7)
O6—C261.330 (6)C36—C411.409 (7)
O6—C271.442 (6)C37—C381.359 (7)
C6—C71.392 (7)C37—H37A0.9300
C6—H6A0.9300C38—C391.381 (8)
N6—C511.363 (6)C38—H38A0.9300
N6—C521.384 (6)C39—C401.385 (8)
N6—H6B0.8600C39—H39A0.9300
C7—H7A0.9300C40—C411.401 (7)
C8—C151.358 (7)C40—H40A0.9300
C8—C91.440 (7)C42—C431.478 (7)
C9—C101.399 (7)C44—H44A0.9600
C9—C141.402 (7)C44—H44B0.9600
O9—C431.333 (7)C44—H44C0.9600
O9—C441.437 (6)C45—C521.372 (7)
O10—C431.198 (6)C45—C461.422 (7)
C10—C111.367 (7)C46—C471.392 (7)
C10—H10A0.9300C46—C511.432 (7)
C11—C121.395 (8)C47—C481.369 (8)
C11—H11A0.9300C47—H47A0.9300
O11—C531.307 (6)C48—C491.388 (8)
O11—C541.438 (6)C48—H48A0.9300
C12—C131.346 (8)C49—C501.361 (8)
C12—H12A0.9300C49—H49A0.9300
O12—C531.214 (6)C50—C511.378 (7)
C13—C141.390 (7)C50—H50A0.9300
C13—H13A0.9300C52—C531.482 (7)
O13—C551.259 (9)C54—H54A0.9600
O13—H13B0.8200C54—H54B0.9600
C15—C161.447 (7)C54—H54C0.9600
C17—H17A0.9600C55—C561.427 (8)
C17—H17B0.9600C55—H55A0.9700
C17—H17C0.9600C55—H55B0.9700
C18—C251.376 (7)C56—H56A0.9600
C18—C191.426 (7)C56—H56B0.9600
C19—C201.394 (7)C56—H56C0.9600
C15—N2—C14109.1 (5)O6—C27—H27B109.5
C15—N2—H2A125.5H27A—C27—H27B109.5
C14—N2—H2A125.5O6—C27—H27C109.5
C8—C1—C2112.0 (4)H27A—C27—H27C109.5
C8—C1—C18113.5 (4)H27B—C27—H27C109.5
C2—C1—C18114.6 (4)C29—C28—C35112.2 (4)
C8—C1—H1A105.2C29—C28—C45113.6 (5)
C2—C1—H1A105.2C35—C28—C45112.7 (5)
C18—C1—H1A105.2C29—C28—H28A105.9
O1—N1—O2123.5 (7)C35—C28—H28A105.9
O1—N1—C5118.3 (7)C45—C28—H28A105.9
O2—N1—C5118.2 (6)C30—C29—C34116.7 (6)
C3—C2—C7117.4 (5)C30—C29—C28121.2 (5)
C3—C2—C1118.6 (5)C34—C29—C28122.1 (5)
C7—C2—C1124.0 (5)C29—C30—C31122.7 (6)
C16—O3—C17116.3 (5)C29—C30—H30A118.6
C24—N3—C25108.7 (5)C31—C30—H30A118.6
C24—N3—H3A125.6C32—C31—C30117.9 (6)
C25—N3—H3A125.6C32—C31—H31A121.0
C2—C3—C4122.7 (6)C30—C31—H31A121.0
C2—C3—H3B118.6C33—C32—C31121.7 (6)
C4—C3—H3B118.6C33—C32—N4119.5 (7)
O8—N4—O7122.5 (7)C31—C32—N4118.8 (6)
O8—N4—C32119.0 (7)C32—C33—C34118.9 (6)
O7—N4—C32118.1 (7)C32—C33—H33A120.6
C3—C4—C5117.6 (6)C34—C33—H33A120.6
C3—C4—H4A121.2C33—C34—C29122.1 (6)
C5—C4—H4A121.2C33—C34—H34A118.9
C6—C5—C4122.7 (6)C29—C34—H34A118.9
C6—C5—N1118.3 (6)C42—C35—C36105.5 (5)
C4—C5—N1119.1 (6)C42—C35—C28125.2 (5)
C41—N5—C42108.9 (5)C36—C35—C28129.2 (5)
C41—N5—H5A125.5C37—C36—C41118.1 (5)
C42—N5—H5A125.5C37—C36—C35134.0 (5)
C26—O6—C27115.2 (5)C41—C36—C35107.8 (5)
C5—C6—C7117.8 (6)C38—C37—C36119.3 (6)
C5—C6—H6A121.1C38—C37—H37A120.3
C7—C6—H6A121.1C36—C37—H37A120.3
C51—N6—C52108.8 (5)C37—C38—C39122.4 (6)
C51—N6—H6B125.6C37—C38—H38A118.8
C52—N6—H6B125.6C39—C38—H38A118.8
C2—C7—C6121.7 (6)C40—C39—C38120.6 (6)
C2—C7—H7A119.1C40—C39—H39A119.7
C6—C7—H7A119.1C38—C39—H39A119.7
C15—C8—C9106.3 (5)C39—C40—C41117.6 (6)
C15—C8—C1125.8 (5)C39—C40—H40A121.2
C9—C8—C1127.9 (5)C41—C40—H40A121.2
C10—C9—C14117.4 (5)N5—C41—C40130.6 (6)
C10—C9—C8135.7 (5)N5—C41—C36107.3 (5)
C14—C9—C8106.7 (5)C40—C41—C36122.0 (6)
C43—O9—C44116.1 (5)C35—C42—N5110.5 (5)
C11—C10—C9120.0 (6)C35—C42—C43133.6 (6)
C11—C10—H10A120.0N5—C42—C43115.6 (5)
C9—C10—H10A120.0O10—C43—O9123.8 (6)
C10—C11—C12120.6 (6)O10—C43—C42124.9 (6)
C10—C11—H11A119.7O9—C43—C42111.2 (5)
C12—C11—H11A119.7O9—C44—H44A109.5
C53—O11—C54114.6 (5)O9—C44—H44B109.5
C13—C12—C11121.3 (6)H44A—C44—H44B109.5
C13—C12—H12A119.3O9—C44—H44C109.5
C11—C12—H12A119.3H44A—C44—H44C109.5
C12—C13—C14118.3 (6)H44B—C44—H44C109.5
C12—C13—H13A120.9C52—C45—C46107.4 (5)
C14—C13—H13A120.9C52—C45—C28122.6 (5)
C55—O13—H13B109.5C46—C45—C28129.9 (5)
N2—C14—C13130.1 (6)C47—C46—C45137.0 (5)
N2—C14—C9107.6 (5)C47—C46—C51116.8 (5)
C13—C14—C9122.3 (6)C45—C46—C51106.2 (5)
C8—C15—N2110.3 (5)C48—C47—C46120.0 (6)
C8—C15—C16127.8 (5)C48—C47—H47A120.0
N2—C15—C16121.8 (5)C46—C47—H47A120.0
O4—C16—O3122.5 (5)C47—C48—C49121.1 (6)
O4—C16—C15126.5 (5)C47—C48—H48A119.5
O3—C16—C15111.0 (5)C49—C48—H48A119.5
O3—C17—H17A109.5C50—C49—C48121.9 (6)
O3—C17—H17B109.5C50—C49—H49A119.1
H17A—C17—H17B109.5C48—C49—H49A119.1
O3—C17—H17C109.5C49—C50—C51117.2 (6)
H17A—C17—H17C109.5C49—C50—H50A121.4
H17B—C17—H17C109.5C51—C50—H50A121.4
C25—C18—C19106.1 (5)N6—C51—C50128.8 (5)
C25—C18—C1124.0 (5)N6—C51—C46108.0 (5)
C19—C18—C1129.8 (5)C50—C51—C46123.1 (5)
C20—C19—C24117.1 (5)C45—C52—N6109.6 (5)
C20—C19—C18136.6 (5)C45—C52—C53130.5 (5)
C24—C19—C18106.3 (5)N6—C52—C53119.7 (5)
C21—C20—C19120.6 (6)O12—C53—O11125.5 (5)
C21—C20—H20A119.7O12—C53—C52121.8 (5)
C19—C20—H20A119.7O11—C53—C52112.8 (5)
C20—C21—C22121.2 (6)O11—C54—H54A109.5
C20—C21—H21A119.4O11—C54—H54B109.5
C22—C21—H21A119.4H54A—C54—H54B109.5
C23—C22—C21121.2 (6)O11—C54—H54C109.5
C23—C22—H22A119.4H54A—C54—H54C109.5
C21—C22—H22A119.4H54B—C54—H54C109.5
C22—C23—C24116.7 (6)O13—C55—C56127.6 (9)
C22—C23—H23A121.7O13—C55—H55A105.4
C24—C23—H23A121.7C56—C55—H55A105.4
N3—C24—C23128.0 (5)O13—C55—H55B105.4
N3—C24—C19108.8 (5)C56—C55—H55B105.4
C23—C24—C19123.2 (5)H55A—C55—H55B106.0
N3—C25—C18110.1 (5)C55—C56—H56A109.5
N3—C25—C26121.6 (5)C55—C56—H56B109.5
C18—C25—C26128.3 (5)H56A—C56—H56B109.5
O5—C26—O6124.0 (5)C55—C56—H56C109.5
O5—C26—C25124.7 (5)H56A—C56—H56C109.5
O6—C26—C25111.3 (5)H56B—C56—H56C109.5
O6—C27—H27A109.5
C8—C1—C2—C3−67.2 (6)C35—C28—C29—C30−154.9 (5)
C18—C1—C2—C3161.6 (5)C45—C28—C29—C3075.9 (7)
C8—C1—C2—C7112.2 (6)C35—C28—C29—C3425.8 (7)
C18—C1—C2—C7−19.0 (7)C45—C28—C29—C34−103.4 (6)
C7—C2—C3—C4−1.8 (9)C34—C29—C30—C31−0.2 (10)
C1—C2—C3—C4177.6 (5)C28—C29—C30—C31−179.5 (6)
C2—C3—C4—C5−0.4 (9)C29—C30—C31—C320.3 (11)
C3—C4—C5—C61.4 (9)C30—C31—C32—C330.6 (10)
C3—C4—C5—N1−177.5 (6)C30—C31—C32—N4177.8 (7)
O1—N1—C5—C6177.4 (7)O8—N4—C32—C33164.3 (7)
O2—N1—C5—C6−2.3 (9)O7—N4—C32—C33−9.2 (10)
O1—N1—C5—C4−3.6 (10)O8—N4—C32—C31−12.9 (11)
O2—N1—C5—C4176.7 (6)O7—N4—C32—C31173.5 (7)
C4—C5—C6—C7−0.2 (9)C31—C32—C33—C34−1.7 (10)
N1—C5—C6—C7178.8 (5)N4—C32—C33—C34−178.8 (6)
C3—C2—C7—C63.1 (8)C32—C33—C34—C291.8 (9)
C1—C2—C7—C6−176.3 (5)C30—C29—C34—C33−0.9 (8)
C5—C6—C7—C2−2.2 (9)C28—C29—C34—C33178.4 (5)
C2—C1—C8—C15141.4 (5)C29—C28—C35—C4277.0 (7)
C18—C1—C8—C15−86.9 (6)C45—C28—C35—C42−153.3 (5)
C2—C1—C8—C9−35.8 (7)C29—C28—C35—C36−98.6 (6)
C18—C1—C8—C995.9 (6)C45—C28—C35—C3631.1 (8)
C15—C8—C9—C10176.7 (6)C42—C35—C36—C37−176.1 (6)
C1—C8—C9—C10−5.7 (10)C28—C35—C36—C370.2 (10)
C15—C8—C9—C141.5 (6)C42—C35—C36—C412.2 (6)
C1—C8—C9—C14179.2 (5)C28—C35—C36—C41178.5 (5)
C14—C9—C10—C11−1.8 (8)C41—C36—C37—C38−0.9 (8)
C8—C9—C10—C11−176.5 (6)C35—C36—C37—C38177.3 (6)
C9—C10—C11—C120.2 (9)C36—C37—C38—C392.2 (9)
C10—C11—C12—C130.6 (10)C37—C38—C39—C40−2.1 (10)
C11—C12—C13—C140.4 (10)C38—C39—C40—C410.5 (9)
C15—N2—C14—C13179.8 (6)C42—N5—C41—C40178.0 (6)
C15—N2—C14—C9−0.8 (6)C42—N5—C41—C361.3 (6)
C12—C13—C14—N2177.2 (6)C39—C40—C41—N5−175.5 (6)
C12—C13—C14—C9−2.1 (9)C39—C40—C41—C360.7 (8)
C10—C9—C14—N2−176.6 (5)C37—C36—C41—N5176.5 (5)
C8—C9—C14—N2−0.5 (6)C35—C36—C41—N5−2.1 (6)
C10—C9—C14—C132.8 (8)C37—C36—C41—C40−0.6 (8)
C8—C9—C14—C13179.0 (5)C35—C36—C41—C40−179.2 (5)
C9—C8—C15—N2−2.1 (6)C36—C35—C42—N5−1.4 (6)
C1—C8—C15—N2−179.8 (5)C28—C35—C42—N5−177.9 (5)
C9—C8—C15—C16−178.3 (5)C36—C35—C42—C43170.9 (6)
C1—C8—C15—C164.0 (9)C28—C35—C42—C43−5.5 (9)
C14—N2—C15—C81.8 (6)C41—N5—C42—C350.1 (6)
C14—N2—C15—C16178.3 (5)C41—N5—C42—C43−173.8 (4)
C17—O3—C16—O4−1.4 (8)C44—O9—C43—O101.7 (9)
C17—O3—C16—C15178.1 (5)C44—O9—C43—C42−177.4 (5)
C8—C15—C16—O4−13.5 (9)C35—C42—C43—O10−167.3 (6)
N2—C15—C16—O4170.7 (6)N5—C42—C43—O104.7 (8)
C8—C15—C16—O3167.0 (5)C35—C42—C43—O911.8 (9)
N2—C15—C16—O3−8.8 (7)N5—C42—C43—O9−176.2 (5)
C8—C1—C18—C25151.5 (5)C29—C28—C45—C52−162.7 (5)
C2—C1—C18—C25−78.0 (6)C35—C28—C45—C5268.3 (7)
C8—C1—C18—C19−28.3 (8)C29—C28—C45—C4617.1 (8)
C2—C1—C18—C19102.1 (6)C35—C28—C45—C46−111.9 (7)
C25—C18—C19—C20−178.6 (6)C52—C45—C46—C47177.4 (7)
C1—C18—C19—C201.3 (10)C28—C45—C46—C47−2.4 (11)
C25—C18—C19—C24−1.4 (6)C52—C45—C46—C51−0.4 (6)
C1—C18—C19—C24178.5 (5)C28—C45—C46—C51179.8 (5)
C24—C19—C20—C211.3 (8)C45—C46—C47—C48−176.4 (7)
C18—C19—C20—C21178.2 (6)C51—C46—C47—C481.2 (9)
C19—C20—C21—C220.6 (9)C46—C47—C48—C49−0.1 (10)
C20—C21—C22—C23−0.5 (10)C47—C48—C49—C500.4 (11)
C21—C22—C23—C24−1.3 (9)C48—C49—C50—C51−1.9 (10)
C25—N3—C24—C23−178.0 (6)C52—N6—C51—C50−174.8 (6)
C25—N3—C24—C19−0.1 (6)C52—N6—C51—C460.4 (6)
C22—C23—C24—N3−179.1 (6)C49—C50—C51—N6177.6 (6)
C22—C23—C24—C193.3 (9)C49—C50—C51—C463.1 (9)
C20—C19—C24—N3178.7 (5)C47—C46—C51—N6−178.3 (5)
C18—C19—C24—N31.0 (6)C45—C46—C51—N60.0 (6)
C20—C19—C24—C23−3.3 (8)C47—C46—C51—C50−2.8 (9)
C18—C19—C24—C23179.0 (5)C45—C46—C51—C50175.5 (5)
C24—N3—C25—C18−0.8 (6)C46—C45—C52—N60.6 (6)
C24—N3—C25—C26179.4 (5)C28—C45—C52—N6−179.6 (5)
C19—C18—C25—N31.4 (6)C46—C45—C52—C53−174.8 (5)
C1—C18—C25—N3−178.5 (4)C28—C45—C52—C535.0 (10)
C19—C18—C25—C26−178.9 (5)C51—N6—C52—C45−0.6 (6)
C1—C18—C25—C261.2 (9)C51—N6—C52—C53175.4 (5)
C27—O6—C26—O5−0.1 (8)C54—O11—C53—O12−0.2 (9)
C27—O6—C26—C25−179.1 (5)C54—O11—C53—C52−178.7 (5)
N3—C25—C26—O5−176.8 (6)C45—C52—C53—O123.1 (10)
C18—C25—C26—O53.5 (10)N6—C52—C53—O12−171.9 (5)
N3—C25—C26—O62.2 (7)C45—C52—C53—O11−178.3 (6)
C18—C25—C26—O6−177.5 (5)N6—C52—C53—O116.7 (7)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2A···O13i0.862.002.814 (7)157
N3—H3A···O4ii0.862.052.892 (6)166
N5—H5A···O12iii0.862.012.848 (6)163
N6—H6B···O10iv0.862.162.984 (6)160
O13—H13B···O50.821.912.733 (7)177
Symmetry codes: (i) x, y+1, z; (ii) −x+2, −y+1, −z; (iii) −x+1, −y+1, −z+1; (iv) x, y−1, z.
 

Acknowledgements

The authors thank the Center of Testing and Analysis, Nanjing University, for support.

Funding information

Funding for this research was provided by: Natural Science Foundation of Jiangsu Province (grant No. BK20181486); Natural Science Foundation of the Jiangsu Higher Education Institutions (grant No. 17KJB320001); Qing Lan Project of Jiangsu Province; Training Program of Students Innovation and Entrepreneurship in Jiangsu Province (grant No. 202012920001Y).

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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.

Journal logoIUCrDATA
ISSN: 2414-3146
Volume 6| Part 2| February 2021| x210057
https://doi.org/10.1107/S2414314621000572
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