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Acta Crystallographica Section E: Structure Reports Online logoLink to Acta Crystallographica Section E: Structure Reports Online
. 2011 Jun 25;67(Pt 7):o1799. doi: 10.1107/S1600536811023890

9-Ethyl-N-(3-nitro­benzyl­idene)-9H-carbazol-3-amine

R Archana a, E Yamuna b, K J Rajendra Prasad b, A Thiruvalluvar a,*, R J Butcher c
PMCID: PMC3151935  PMID: 21837172

Abstract

The title compound, C21H17N3O2, crystallizes with two mol­ecules in the asymmetric unit. The carbazole groups show relatively small deviations from planarity [maximum displacements from the mean carbazole plane are 0.077 (7) and 0.101 (7) Å]. The dihedral angles between the 3-nitro­benzyl­idene­amine and carbazole groups are 37.9 (1) and 37.0 (1)° in the two mol­ecules.

Related literature

For anti-convulsant and diuretic activity of rimcazole (systematic name 9-{3-[(3R,5S)-3,5-dimethyl­piperazin-1-yl]prop­yl}-9H-carbazole) and other N-alkyl­amino carbazoles, see: Ferris et al. (1986 ▶), Shoeb et al. (1973 ▶). For a related structure, see: Archana et al. (2010 ▶).graphic file with name e-67-o1799-scheme1.jpg

Experimental

Crystal data

  • C21H17N3O2

  • M r = 343.38

  • Monoclinic, Inline graphic

  • a = 8.1550 (4) Å

  • b = 13.5093 (7) Å

  • c = 16.0248 (9) Å

  • β = 103.899 (5)°

  • V = 1713.74 (16) Å3

  • Z = 4

  • Cu Kα radiation

  • μ = 0.71 mm−1

  • T = 295 K

  • 0.44 × 0.41 × 0.35 mm

Data collection

  • Oxford Diffraction Xcalibur Ruby Gemini diffractometer

  • Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010 ▶) T min = 0.830, T max = 1.000

  • 6983 measured reflections

  • 3509 independent reflections

  • 2458 reflections with I > 2σ(I)

  • R int = 0.034

Refinement

  • R[F 2 > 2σ(F 2)] = 0.080

  • wR(F 2) = 0.246

  • S = 1.08

  • 3509 reflections

  • 471 parameters

  • 1 restraint

  • H-atom parameters constrained

  • Δρmax = 0.32 e Å−3

  • Δρmin = −0.29 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2010 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: PLATON.

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811023890/ya2140sup1.cif

e-67-o1799-sup1.cif (31.4KB, cif)

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811023890/ya2140Isup2.hkl

e-67-o1799-Isup2.hkl (168.6KB, hkl)

Supplementary material file. DOI: 10.1107/S1600536811023890/ya2140Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

RJB acknowledges the NSF MRI program (grant No. CHE-0619278) for providing funds for the purchase of an X-ray diffractometer.

supplementary crystallographic information

Comment

N-Alkylamino carbazoles show significant anti-convulsant and diuretic activity (Shoeb et al., 1973). One of them, rimcazole is a well known anti-pyretic and neuroleptic agent (Ferris et al., 1986). It was found to be a specific competitive antagonist of s-sites in the brain; it reverses psychotic conditions induced in humans by phencyclidine and/or s-opiod antagonists, probably by binding to receptors in the brain.

Archana et al. (2010) have reported a crystal structure of substituted carbazole derivative, in which the carbazole unit is almost planar. The title compound, C21H17N3O2, crystallizes with two molecules (A and B) in the asymmetric unit (Fig. 1). The carbazole groups show relatively small deviations from planarity [maximum displacement of the C9A atom from the mean carbazole plane in molecule A is equal to 0.077 (7) Å, displacement of the C9B atom in B is 0.101 (7) Å]. The dihedral angles between the 3-nitro-benzylideneamine group and the carbazole group are 37.9 (1)° and 37.0 (1)° in A and B respectively.

Experimental

Herein, we report a simple and effective method of high-yield synthesis of the title compound. A mixture of m-nitrobenzaldehyde (0.154 g, 0.001 mol), 3-amino-9-ethylcarbazole (0.210 g, 0.001 mol) and sodium bicarbonate (0.080 g, 0.001 mol) was ground and kept at room temperature for 2 h. The reaction was monitored by TLC. Then the solid was quenched with crushed ice under stirring and acidified with dilute hydrochloric acid till the solution became acidic (litmus color change from blue to red). The product was extracted with ethylacetate and dried over anhydrous sodium sulfate. Upon removal of the solvent, a yellow crude product was obtained. It was purified by column chromatography over silica gel using petroleum ether: ethylacetate (95:5, v/v) mixture as eluent to afford the title compound (yield: 0.274 g, 80%); the pale-orange product was recrystallized from ethanol.

Refinement

As there are no significant anomalous scatterers in the molecule, the Friedel pairs were merged. H atoms were positioned geometrically and allowed to ride on their parent atoms, with C—H = 0.93, 0.96 and 0.97 Å for Csp2, methyl and methylene H atoms, respectively. Uiso(H) = xUeq(C), where x = 1.5 for methyl H atoms and 1.2 for other C-bound H atoms.

Figures

Fig. 1.

Fig. 1.

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Asymmetric unit of the title compound; displacement ellipsoids are drawn at the 30% probability level. H atoms were omitted for clarity.

Crystal data

C21H17N3O2 F(000) = 720
Mr = 343.38 Dx = 1.331 Mg m−3
Monoclinic, P21 Melting point: 352 K
Hall symbol: P 2yb Cu Kα radiation, λ = 1.54184 Å
a = 8.1550 (4) Å Cell parameters from 2308 reflections
b = 13.5093 (7) Å θ = 5.6–73.4°
c = 16.0248 (9) Å µ = 0.71 mm−1
β = 103.899 (5)° T = 295 K
V = 1713.74 (16) Å3 Block, pale-orange
Z = 4 0.44 × 0.41 × 0.35 mm
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Data collection

Oxford Diffraction Xcalibur Ruby Gemini diffractometer 3509 independent reflections
Radiation source: Enhance (Cu) X-ray Source 2458 reflections with I > 2σ(I)
graphite Rint = 0.034
Detector resolution: 10.5081 pixels mm-1 θmax = 73.6°, θmin = 5.6°
ω scans h = −10→7
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010) k = −16→9
Tmin = 0.830, Tmax = 1.000 l = −19→18
6983 measured reflections
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Refinement

Refinement on F2 Primary atom site location: structure-invariant direct methods
Least-squares matrix: full Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.080 Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.246 H-atom parameters constrained
S = 1.08 w = 1/[σ2(Fo2) + (0.1348P)2 + 0.51P] where P = (Fo2 + 2Fc2)/3
3509 reflections (Δ/σ)max = 0.001
471 parameters Δρmax = 0.32 e Å−3
1 restraint Δρmin = −0.29 e Å−3
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Special details

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles
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 > 2σ(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.
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Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

x y z Uiso*/Ueq
O1A −0.0282 (8) 0.1393 (7) 0.4830 (4) 0.105 (3)
O2A 0.1202 (9) 0.1178 (9) 0.6087 (4) 0.140 (4)
N3A 0.1053 (9) 0.1305 (6) 0.5327 (4) 0.082 (3)
N12A 0.1520 (8) 0.1142 (5) −0.1190 (3) 0.068 (2)
N14A 0.2402 (7) 0.1332 (5) 0.2351 (3) 0.0687 (19)
C1A 0.3254 (9) 0.0611 (6) 0.0235 (4) 0.072 (3)
C2A 0.3430 (9) 0.0681 (6) 0.1102 (5) 0.068 (2)
C3A 0.2341 (9) 0.1275 (6) 0.1455 (4) 0.066 (2)
C4A 0.1066 (8) 0.1804 (6) 0.0897 (4) 0.064 (2)
C5A 0.0895 (8) 0.1752 (5) 0.0019 (4) 0.059 (2)
C6A −0.0291 (8) 0.2176 (5) −0.0709 (4) 0.061 (2)
C7A −0.1635 (9) 0.2809 (7) −0.0821 (5) 0.074 (3)
C8A −0.2614 (10) 0.3017 (7) −0.1638 (5) 0.079 (3)
C9A −0.2195 (10) 0.2607 (7) −0.2351 (5) 0.079 (3)
C10A −0.0813 (10) 0.1994 (6) −0.2275 (4) 0.068 (3)
C11A 0.0148 (9) 0.1772 (6) −0.1449 (5) 0.067 (2)
C13A 0.1988 (8) 0.1136 (5) −0.0308 (4) 0.063 (2)
C15A 0.3788 (9) 0.1236 (6) 0.2892 (4) 0.069 (3)
C16A 0.2434 (11) 0.0668 (7) −0.1766 (5) 0.077 (3)
C17A 0.3884 (10) 0.1283 (8) −0.1880 (5) 0.086 (3)
C31A 0.3893 (8) 0.1261 (6) 0.3828 (4) 0.066 (2)
C32A 0.2451 (9) 0.1300 (6) 0.4137 (4) 0.066 (2)
C33A 0.2603 (9) 0.1313 (6) 0.5004 (5) 0.070 (2)
C34A 0.4152 (11) 0.1297 (7) 0.5583 (5) 0.083 (3)
C35A 0.5585 (10) 0.1295 (8) 0.5269 (5) 0.083 (3)
C36A 0.5457 (9) 0.1265 (7) 0.4407 (5) 0.075 (3)
O1B 0.4490 (7) 0.8842 (5) 0.4146 (4) 0.093 (2)
O2B 0.6022 (9) 0.8772 (6) 0.5430 (4) 0.105 (3)
N3B 0.5850 (9) 0.8824 (5) 0.4656 (4) 0.079 (2)
N12B 0.6177 (7) 0.9094 (5) −0.1890 (3) 0.0683 (19)
N14B 0.7154 (7) 0.8953 (5) 0.1660 (4) 0.068 (2)
C1B 0.7939 (10) 0.9677 (6) −0.0465 (5) 0.076 (3)
C2B 0.8102 (9) 0.9611 (7) 0.0408 (4) 0.070 (3)
C3B 0.7059 (8) 0.8992 (6) 0.0763 (4) 0.063 (2)
C4B 0.5824 (8) 0.8446 (5) 0.0241 (4) 0.061 (2)
C5B 0.5615 (8) 0.8491 (5) −0.0652 (4) 0.060 (2)
C6B 0.4411 (8) 0.8060 (6) −0.1376 (4) 0.066 (3)
C7B 0.3071 (9) 0.7411 (7) −0.1470 (5) 0.072 (3)
C8B 0.2099 (10) 0.7211 (8) −0.2275 (5) 0.084 (3)
C9B 0.2454 (10) 0.7646 (7) −0.3004 (5) 0.083 (3)
C10B 0.3792 (10) 0.8263 (7) −0.2938 (4) 0.078 (3)
C11B 0.4788 (9) 0.8478 (5) −0.2124 (4) 0.063 (2)
C13B 0.6670 (9) 0.9118 (6) −0.0994 (4) 0.065 (2)
C15B 0.8523 (9) 0.9092 (6) 0.2203 (4) 0.069 (3)
C16B 0.7073 (11) 0.9593 (6) −0.2463 (5) 0.076 (3)
C17B 0.8592 (11) 0.9026 (8) −0.2563 (6) 0.093 (3)
C31B 0.8645 (9) 0.9048 (6) 0.3131 (5) 0.067 (2)
C32B 0.7214 (9) 0.8965 (6) 0.3455 (4) 0.068 (2)
C33B 0.7393 (9) 0.8892 (6) 0.4328 (4) 0.069 (2)
C34B 0.8935 (10) 0.8861 (7) 0.4902 (5) 0.077 (3)
C35B 1.0380 (10) 0.8944 (8) 0.4593 (5) 0.082 (3)
C36B 1.0220 (9) 0.9035 (7) 0.3711 (5) 0.075 (3)
H1A 0.39812 0.02142 0.00140 0.0854*
H2A 0.42871 0.03277 0.14695 0.0816*
H4A 0.03272 0.21936 0.11161 0.0771*
H7A −0.18962 0.31035 −0.03446 0.0883*
H8A −0.35475 0.34315 −0.17058 0.0944*
H9A −0.28628 0.27474 −0.28952 0.0952*
H10A −0.05286 0.17356 −0.27590 0.0819*
H15A 0.47691 0.11483 0.27022 0.0823*
H16A 0.16631 0.05586 −0.23212 0.0923*
H16B 0.28490 0.00285 −0.15317 0.0923*
H17A 0.34801 0.19211 −0.21020 0.1293*
H17B 0.44259 0.09613 −0.22762 0.1293*
H17C 0.46804 0.13625 −0.13358 0.1293*
H32A 0.13894 0.13171 0.37583 0.0799*
H34A 0.42308 0.12868 0.61717 0.0991*
H35A 0.66446 0.13148 0.56485 0.1003*
H36A 0.64332 0.12469 0.42032 0.0896*
H1B 0.86486 1.00789 −0.06921 0.0910*
H2B 0.89269 0.99862 0.07747 0.0833*
H4B 0.51235 0.80448 0.04761 0.0734*
H7B 0.28306 0.71125 −0.09897 0.0861*
H8B 0.11890 0.67795 −0.23384 0.1009*
H9B 0.17607 0.75097 −0.35428 0.0997*
H10B 0.40379 0.85356 −0.34270 0.0944*
H15B 0.94904 0.92260 0.20120 0.0821*
H16C 0.74254 1.02441 −0.22340 0.0911*
H16D 0.63074 0.96791 −0.30229 0.0911*
H17D 0.94256 0.90199 −0.20260 0.1391*
H17E 0.90551 0.93350 −0.29948 0.1391*
H17F 0.82695 0.83581 −0.27327 0.1391*
H32B 0.61443 0.89588 0.30842 0.0811*
H34B 0.90132 0.87866 0.54867 0.0927*
H35B 1.14430 0.89386 0.49703 0.0978*
H36B 1.11889 0.90875 0.35045 0.0896*
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Atomic displacement parameters (Å2)

U11 U22 U33 U12 U13 U23
O1A 0.083 (4) 0.151 (6) 0.090 (4) 0.013 (4) 0.037 (3) 0.013 (4)
O2A 0.117 (5) 0.254 (11) 0.058 (3) 0.014 (6) 0.039 (3) 0.011 (5)
N3A 0.088 (4) 0.101 (5) 0.059 (4) 0.005 (4) 0.023 (3) 0.001 (3)
N12A 0.081 (4) 0.075 (4) 0.052 (3) 0.007 (3) 0.026 (3) −0.001 (3)
N14A 0.068 (3) 0.089 (4) 0.052 (3) 0.003 (3) 0.020 (3) 0.003 (3)
C1A 0.077 (4) 0.073 (4) 0.071 (5) 0.014 (4) 0.030 (3) 0.004 (4)
C2A 0.067 (4) 0.067 (4) 0.071 (4) 0.012 (3) 0.018 (3) 0.005 (3)
C3A 0.065 (4) 0.077 (4) 0.060 (4) −0.006 (4) 0.025 (3) −0.003 (4)
C4A 0.061 (3) 0.076 (4) 0.061 (4) 0.001 (3) 0.024 (3) −0.002 (3)
C5A 0.054 (3) 0.071 (4) 0.055 (4) −0.005 (3) 0.019 (3) −0.003 (3)
C6A 0.053 (3) 0.071 (4) 0.062 (4) −0.009 (3) 0.019 (3) 0.001 (3)
C7A 0.068 (4) 0.088 (5) 0.066 (4) 0.003 (4) 0.019 (3) 0.007 (4)
C8A 0.071 (4) 0.092 (5) 0.073 (5) 0.006 (4) 0.017 (3) 0.009 (4)
C9A 0.072 (4) 0.095 (6) 0.070 (5) −0.002 (4) 0.015 (4) 0.018 (4)
C10A 0.080 (4) 0.076 (5) 0.051 (4) −0.005 (4) 0.020 (3) 0.003 (3)
C11A 0.072 (4) 0.072 (4) 0.062 (4) −0.015 (4) 0.026 (3) 0.000 (3)
C13A 0.063 (4) 0.064 (4) 0.065 (4) −0.003 (3) 0.021 (3) −0.003 (3)
C15A 0.060 (4) 0.084 (5) 0.066 (4) −0.002 (4) 0.023 (3) 0.002 (4)
C16A 0.087 (5) 0.081 (5) 0.070 (5) 0.014 (4) 0.033 (4) −0.008 (4)
C17A 0.090 (5) 0.100 (6) 0.079 (5) 0.009 (5) 0.041 (4) −0.003 (5)
C31A 0.066 (4) 0.073 (4) 0.060 (4) 0.000 (4) 0.020 (3) 0.003 (3)
C32A 0.065 (4) 0.076 (4) 0.055 (4) 0.000 (4) 0.009 (3) 0.004 (3)
C33A 0.071 (4) 0.077 (4) 0.066 (4) 0.009 (4) 0.025 (3) 0.005 (4)
C34A 0.097 (5) 0.099 (6) 0.051 (4) 0.007 (5) 0.015 (4) 0.004 (4)
C35A 0.078 (4) 0.102 (6) 0.064 (4) 0.004 (5) 0.005 (3) 0.004 (4)
C36A 0.067 (4) 0.086 (5) 0.071 (4) −0.002 (4) 0.017 (3) 0.006 (4)
O1B 0.071 (3) 0.120 (5) 0.088 (4) −0.006 (3) 0.022 (3) −0.009 (4)
O2B 0.120 (5) 0.140 (6) 0.066 (4) −0.005 (4) 0.043 (3) −0.001 (3)
N3B 0.086 (4) 0.088 (4) 0.069 (4) −0.010 (4) 0.030 (3) −0.006 (3)
N12B 0.076 (3) 0.079 (4) 0.055 (3) −0.005 (3) 0.026 (3) 0.000 (3)
N14B 0.065 (3) 0.076 (4) 0.064 (4) −0.002 (3) 0.020 (3) 0.001 (3)
C1B 0.080 (4) 0.081 (5) 0.070 (4) −0.014 (4) 0.024 (4) 0.002 (4)
C2B 0.070 (4) 0.084 (5) 0.054 (4) −0.011 (4) 0.014 (3) −0.005 (3)
C3B 0.056 (3) 0.076 (4) 0.057 (4) 0.003 (3) 0.015 (3) −0.002 (3)
C4B 0.060 (3) 0.066 (4) 0.057 (4) 0.000 (3) 0.012 (3) 0.001 (3)
C5B 0.065 (4) 0.057 (3) 0.059 (4) −0.005 (3) 0.018 (3) −0.001 (3)
C6B 0.062 (4) 0.083 (5) 0.056 (4) 0.006 (3) 0.023 (3) −0.005 (3)
C7B 0.070 (4) 0.087 (5) 0.061 (4) −0.006 (4) 0.021 (3) −0.007 (4)
C8B 0.068 (4) 0.104 (6) 0.083 (5) −0.007 (4) 0.024 (4) −0.011 (5)
C9B 0.074 (4) 0.115 (7) 0.060 (4) 0.005 (5) 0.015 (3) −0.010 (4)
C10B 0.077 (4) 0.107 (6) 0.053 (4) 0.006 (4) 0.019 (3) −0.008 (4)
C11B 0.069 (4) 0.071 (4) 0.051 (3) 0.006 (3) 0.019 (3) −0.003 (3)
C13B 0.072 (4) 0.071 (4) 0.055 (4) 0.005 (3) 0.020 (3) 0.002 (3)
C15B 0.066 (4) 0.084 (5) 0.057 (4) −0.001 (4) 0.018 (3) −0.003 (3)
C16B 0.098 (5) 0.075 (4) 0.060 (4) −0.003 (4) 0.029 (4) 0.005 (3)
C17B 0.102 (6) 0.105 (6) 0.084 (6) −0.008 (5) 0.048 (5) 0.003 (5)
C31B 0.063 (4) 0.076 (4) 0.061 (4) −0.001 (4) 0.014 (3) −0.004 (4)
C32B 0.071 (4) 0.075 (4) 0.056 (4) 0.004 (4) 0.013 (3) −0.004 (3)
C33B 0.069 (4) 0.075 (4) 0.062 (4) −0.001 (4) 0.016 (3) −0.005 (4)
C34B 0.079 (5) 0.092 (5) 0.058 (4) −0.005 (4) 0.012 (3) −0.004 (4)
C35B 0.071 (4) 0.103 (6) 0.064 (4) −0.002 (4) 0.002 (3) −0.010 (4)
C36B 0.068 (4) 0.090 (5) 0.068 (4) −0.007 (4) 0.019 (3) −0.007 (4)
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Geometric parameters (Å, °)

O1A—N3A 1.190 (10) C16A—H16B 0.9700
O2A—N3A 1.207 (9) C17A—H17B 0.9600
O1B—N3B 1.210 (9) C17A—H17C 0.9600
O2B—N3B 1.216 (9) C17A—H17A 0.9600
N3A—C33A 1.477 (11) C32A—H32A 0.9300
N12A—C13A 1.373 (8) C34A—H34A 0.9300
N12A—C11A 1.388 (10) C35A—H35A 0.9300
N12A—C16A 1.466 (11) C36A—H36A 0.9300
N14A—C15A 1.255 (9) C1B—C2B 1.376 (10)
N14A—C3A 1.427 (8) C1B—C13B 1.392 (11)
N3B—C33B 1.479 (10) C2B—C3B 1.407 (11)
N12B—C11B 1.383 (9) C3B—C4B 1.361 (10)
N12B—C13B 1.395 (8) C4B—C5B 1.401 (9)
N12B—C16B 1.468 (10) C5B—C6B 1.450 (9)
N14B—C3B 1.422 (9) C5B—C13B 1.409 (10)
N14B—C15B 1.254 (9) C6B—C7B 1.381 (11)
C1A—C13A 1.376 (10) C6B—C11B 1.424 (9)
C1A—C2A 1.365 (10) C7B—C8B 1.369 (11)
C2A—C3A 1.412 (11) C8B—C9B 1.399 (12)
C3A—C4A 1.395 (10) C9B—C10B 1.357 (12)
C4A—C5A 1.382 (9) C10B—C11B 1.392 (9)
C5A—C6A 1.443 (9) C15B—C31B 1.468 (10)
C5A—C13A 1.409 (9) C16B—C17B 1.497 (13)
C6A—C7A 1.368 (11) C31B—C32B 1.391 (11)
C6A—C11A 1.427 (10) C31B—C36B 1.393 (11)
C7A—C8A 1.389 (11) C32B—C33B 1.375 (9)
C8A—C9A 1.384 (12) C33B—C34B 1.369 (11)
C9A—C10A 1.380 (12) C34B—C35B 1.388 (12)
C10A—C11A 1.399 (10) C35B—C36B 1.393 (11)
C15A—C31A 1.482 (9) C1B—H1B 0.9300
C16A—C17A 1.492 (13) C2B—H2B 0.9300
C31A—C36A 1.385 (10) C4B—H4B 0.9300
C31A—C32A 1.382 (10) C7B—H7B 0.9300
C32A—C33A 1.365 (10) C8B—H8B 0.9300
C33A—C34A 1.376 (12) C9B—H9B 0.9300
C34A—C35A 1.379 (12) C10B—H10B 0.9300
C35A—C36A 1.361 (11) C15B—H15B 0.9300
C1A—H1A 0.9300 C16B—H16C 0.9700
C2A—H2A 0.9300 C16B—H16D 0.9700
C4A—H4A 0.9300 C17B—H17D 0.9600
C7A—H7A 0.9300 C17B—H17E 0.9600
C8A—H8A 0.9300 C17B—H17F 0.9600
C9A—H9A 0.9300 C32B—H32B 0.9300
C10A—H10A 0.9300 C34B—H34B 0.9300
C15A—H15A 0.9300 C35B—H35B 0.9300
C16A—H16A 0.9700 C36B—H36B 0.9300
O1A—N3A—O2A 122.9 (8) C33A—C32A—H32A 120.00
O1A—N3A—C33A 119.2 (6) C33A—C34A—H34A 121.00
O2A—N3A—C33A 117.9 (7) C35A—C34A—H34A 121.00
C11A—N12A—C13A 108.4 (6) C34A—C35A—H35A 120.00
C11A—N12A—C16A 125.1 (6) C36A—C35A—H35A 120.00
C13A—N12A—C16A 126.0 (6) C31A—C36A—H36A 120.00
C3A—N14A—C15A 119.8 (6) C35A—C36A—H36A 120.00
O1B—N3B—C33B 118.6 (6) C2B—C1B—C13B 117.4 (7)
O2B—N3B—C33B 117.8 (7) C1B—C2B—C3B 122.0 (7)
O1B—N3B—O2B 123.5 (8) N14B—C3B—C2B 122.7 (6)
C11B—N12B—C13B 107.9 (6) N14B—C3B—C4B 117.0 (6)
C13B—N12B—C16B 124.7 (6) C2B—C3B—C4B 120.2 (6)
C11B—N12B—C16B 127.3 (5) C3B—C4B—C5B 119.6 (6)
C3B—N14B—C15B 121.3 (6) C4B—C5B—C6B 133.9 (6)
C2A—C1A—C13A 119.2 (7) C4B—C5B—C13B 119.2 (6)
C1A—C2A—C3A 121.6 (7) C6B—C5B—C13B 106.8 (6)
N14A—C3A—C2A 124.1 (7) C5B—C6B—C7B 135.1 (6)
N14A—C3A—C4A 117.3 (6) C5B—C6B—C11B 105.8 (6)
C2A—C3A—C4A 118.6 (6) C7B—C6B—C11B 119.0 (6)
C3A—C4A—C5A 120.3 (6) C6B—C7B—C8B 119.5 (7)
C4A—C5A—C6A 133.4 (6) C7B—C8B—C9B 121.0 (8)
C4A—C5A—C13A 119.4 (6) C8B—C9B—C10B 121.1 (7)
C6A—C5A—C13A 107.1 (5) C9B—C10B—C11B 118.6 (7)
C7A—C6A—C11A 118.9 (6) N12B—C11B—C6B 109.8 (5)
C5A—C6A—C11A 105.5 (6) N12B—C11B—C10B 129.5 (6)
C5A—C6A—C7A 135.6 (6) C6B—C11B—C10B 120.7 (7)
C6A—C7A—C8A 120.8 (7) N12B—C13B—C1B 128.9 (7)
C7A—C8A—C9A 119.8 (8) N12B—C13B—C5B 109.5 (6)
C8A—C9A—C10A 121.7 (7) C1B—C13B—C5B 121.6 (6)
C9A—C10A—C11A 118.2 (7) N14B—C15B—C31B 122.0 (7)
N12A—C11A—C6A 109.4 (6) N12B—C16B—C17B 112.4 (7)
N12A—C11A—C10A 130.0 (7) C15B—C31B—C32B 121.5 (7)
C6A—C11A—C10A 120.6 (7) C15B—C31B—C36B 120.3 (7)
N12A—C13A—C1A 129.4 (6) C32B—C31B—C36B 118.1 (7)
N12A—C13A—C5A 109.6 (6) C31B—C32B—C33B 119.5 (7)
C1A—C13A—C5A 121.0 (6) N3B—C33B—C32B 118.4 (6)
N14A—C15A—C31A 121.4 (6) N3B—C33B—C34B 118.8 (6)
N12A—C16A—C17A 111.8 (7) C32B—C33B—C34B 122.8 (7)
C15A—C31A—C36A 119.9 (6) C33B—C34B—C35B 118.7 (7)
C15A—C31A—C32A 121.1 (6) C34B—C35B—C36B 119.2 (7)
C32A—C31A—C36A 119.1 (6) C31B—C36B—C35B 121.6 (7)
C31A—C32A—C33A 119.2 (7) C2B—C1B—H1B 121.00
C32A—C33A—C34A 122.0 (7) C13B—C1B—H1B 121.00
N3A—C33A—C32A 118.7 (7) C1B—C2B—H2B 119.00
N3A—C33A—C34A 119.2 (7) C3B—C2B—H2B 119.00
C33A—C34A—C35A 118.4 (7) C3B—C4B—H4B 120.00
C34A—C35A—C36A 120.4 (7) C5B—C4B—H4B 120.00
C31A—C36A—C35A 120.9 (7) C6B—C7B—H7B 120.00
C2A—C1A—H1A 120.00 C8B—C7B—H7B 120.00
C13A—C1A—H1A 120.00 C7B—C8B—H8B 120.00
C1A—C2A—H2A 119.00 C9B—C8B—H8B 119.00
C3A—C2A—H2A 119.00 C8B—C9B—H9B 119.00
C5A—C4A—H4A 120.00 C10B—C9B—H9B 119.00
C3A—C4A—H4A 120.00 C9B—C10B—H10B 121.00
C6A—C7A—H7A 120.00 C11B—C10B—H10B 121.00
C8A—C7A—H7A 120.00 N14B—C15B—H15B 119.00
C9A—C8A—H8A 120.00 C31B—C15B—H15B 119.00
C7A—C8A—H8A 120.00 N12B—C16B—H16C 109.00
C8A—C9A—H9A 119.00 N12B—C16B—H16D 109.00
C10A—C9A—H9A 119.00 C17B—C16B—H16C 109.00
C9A—C10A—H10A 121.00 C17B—C16B—H16D 109.00
C11A—C10A—H10A 121.00 H16C—C16B—H16D 108.00
N14A—C15A—H15A 119.00 C16B—C17B—H17D 110.00
C31A—C15A—H15A 119.00 C16B—C17B—H17E 109.00
N12A—C16A—H16A 109.00 C16B—C17B—H17F 109.00
N12A—C16A—H16B 109.00 H17D—C17B—H17E 109.00
C17A—C16A—H16A 109.00 H17D—C17B—H17F 109.00
C17A—C16A—H16B 109.00 H17E—C17B—H17F 109.00
H16A—C16A—H16B 108.00 C31B—C32B—H32B 120.00
H17B—C17A—H17C 109.00 C33B—C32B—H32B 120.00
C16A—C17A—H17A 110.00 C33B—C34B—H34B 121.00
C16A—C17A—H17B 109.00 C35B—C34B—H34B 121.00
C16A—C17A—H17C 110.00 C34B—C35B—H35B 120.00
H17A—C17A—H17B 109.00 C36B—C35B—H35B 120.00
H17A—C17A—H17C 109.00 C31B—C36B—H36B 119.00
C31A—C32A—H32A 120.00 C35B—C36B—H36B 119.00
O1A—N3A—C33A—C32A −7.9 (13) C6A—C7A—C8A—C9A −2.2 (13)
O1A—N3A—C33A—C34A 174.5 (9) C7A—C8A—C9A—C10A −0.3 (14)
O2A—N3A—C33A—C32A 169.9 (10) C8A—C9A—C10A—C11A 1.6 (13)
O2A—N3A—C33A—C34A −7.8 (13) C9A—C10A—C11A—N12A 175.9 (8)
C13A—N12A—C11A—C6A −0.6 (8) C9A—C10A—C11A—C6A −0.4 (12)
C13A—N12A—C11A—C10A −177.3 (8) N14A—C15A—C31A—C36A −172.7 (8)
C16A—N12A—C11A—C6A −173.6 (7) N14A—C15A—C31A—C32A 6.0 (12)
C16A—N12A—C11A—C10A 9.8 (13) C15A—C31A—C36A—C35A 179.5 (9)
C11A—N12A—C13A—C1A 178.7 (8) C15A—C31A—C32A—C33A 179.4 (8)
C11A—N12A—C13A—C5A 1.2 (8) C36A—C31A—C32A—C33A −1.9 (12)
C16A—N12A—C13A—C1A −8.5 (13) C32A—C31A—C36A—C35A 0.8 (14)
C16A—N12A—C13A—C5A 174.0 (7) C31A—C32A—C33A—C34A 0.6 (13)
C11A—N12A—C16A—C17A 91.1 (9) C31A—C32A—C33A—N3A −177.0 (7)
C13A—N12A—C16A—C17A −80.7 (10) N3A—C33A—C34A—C35A 179.4 (8)
C15A—N14A—C3A—C2A 32.0 (12) C32A—C33A—C34A—C35A 1.8 (14)
C15A—N14A—C3A—C4A −151.4 (8) C33A—C34A—C35A—C36A −2.9 (15)
C3A—N14A—C15A—C31A −178.2 (7) C34A—C35A—C36A—C31A 1.6 (15)
O1B—N3B—C33B—C34B −179.3 (8) C13B—C1B—C2B—C3B 1.2 (12)
O2B—N3B—C33B—C32B −179.1 (8) C2B—C1B—C13B—N12B 175.9 (8)
O1B—N3B—C33B—C32B −0.5 (11) C2B—C1B—C13B—C5B −1.4 (12)
O2B—N3B—C33B—C34B 2.1 (12) C1B—C2B—C3B—N14B −176.7 (8)
C16B—N12B—C11B—C6B 173.7 (7) C1B—C2B—C3B—C4B −1.1 (12)
C16B—N12B—C11B—C10B −7.8 (13) N14B—C3B—C4B—C5B 177.0 (6)
C11B—N12B—C16B—C17B −96.0 (9) C2B—C3B—C4B—C5B 1.1 (11)
C13B—N12B—C16B—C17B 79.7 (9) C3B—C4B—C5B—C6B −176.4 (8)
C16B—N12B—C13B—C1B 7.6 (13) C3B—C4B—C5B—C13B −1.3 (10)
C11B—N12B—C13B—C1B −176.0 (8) C4B—C5B—C6B—C7B −3.7 (15)
C11B—N12B—C13B—C5B 1.6 (8) C4B—C5B—C6B—C11B 174.1 (7)
C13B—N12B—C11B—C10B 176.0 (8) C13B—C5B—C6B—C7B −179.3 (9)
C16B—N12B—C13B—C5B −174.8 (7) C13B—C5B—C6B—C11B −1.5 (8)
C13B—N12B—C11B—C6B −2.6 (8) C4B—C5B—C13B—N12B −176.4 (6)
C15B—N14B—C3B—C2B −31.6 (12) C4B—C5B—C13B—C1B 1.4 (11)
C3B—N14B—C15B—C31B −179.6 (7) C6B—C5B—C13B—N12B 0.0 (8)
C15B—N14B—C3B—C4B 152.6 (8) C6B—C5B—C13B—C1B 177.8 (7)
C2A—C1A—C13A—N12A −176.3 (7) C5B—C6B—C7B—C8B 175.2 (9)
C13A—C1A—C2A—C3A 0.3 (12) C11B—C6B—C7B—C8B −2.3 (12)
C2A—C1A—C13A—C5A 0.9 (11) C5B—C6B—C11B—N12B 2.5 (8)
C1A—C2A—C3A—C4A −0.4 (12) C5B—C6B—C11B—C10B −176.2 (7)
C1A—C2A—C3A—N14A 176.2 (7) C7B—C6B—C11B—N12B −179.3 (7)
N14A—C3A—C4A—C5A −177.6 (7) C7B—C6B—C11B—C10B 2.0 (11)
C2A—C3A—C4A—C5A −0.7 (11) C6B—C7B—C8B—C9B 0.7 (14)
C3A—C4A—C5A—C13A 1.9 (11) C7B—C8B—C9B—C10B 1.4 (15)
C3A—C4A—C5A—C6A 177.9 (7) C8B—C9B—C10B—C11B −1.7 (14)
C4A—C5A—C6A—C11A −175.5 (8) C9B—C10B—C11B—N12B −178.4 (8)
C13A—C5A—C6A—C7A 179.5 (9) C9B—C10B—C11B—C6B 0.0 (12)
C13A—C5A—C6A—C11A 0.8 (8) N14B—C15B—C31B—C32B −7.7 (13)
C4A—C5A—C13A—N12A 175.7 (6) N14B—C15B—C31B—C36B 168.9 (8)
C4A—C5A—C13A—C1A −2.1 (10) C15B—C31B—C32B—C33B 177.8 (8)
C6A—C5A—C13A—N12A −1.3 (8) C36B—C31B—C32B—C33B 1.2 (12)
C6A—C5A—C13A—C1A −179.0 (7) C15B—C31B—C36B—C35B −176.8 (9)
C4A—C5A—C6A—C7A 3.1 (15) C32B—C31B—C36B—C35B −0.1 (13)
C11A—C6A—C7A—C8A 3.3 (12) C31B—C32B—C33B—N3B 178.8 (7)
C5A—C6A—C11A—N12A −0.2 (8) C31B—C32B—C33B—C34B −2.4 (13)
C5A—C6A—C11A—C10A 176.9 (7) N3B—C33B—C34B—C35B −178.8 (8)
C7A—C6A—C11A—N12A −179.1 (7) C32B—C33B—C34B—C35B 2.5 (14)
C7A—C6A—C11A—C10A −2.1 (11) C33B—C34B—C35B—C36B −1.3 (15)
C5A—C6A—C7A—C8A −175.2 (8) C34B—C35B—C36B—C31B 0.2 (15)
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Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: YA2140).

References

  1. Archana, R., Prabakaran, K., Rajendra Prasad, K. J., Thiruvalluvar, A. & Butcher, R. J. (2010). Acta Cryst. E66, o3146. [DOI] [PMC free article] [PubMed]
  2. Ferris, R. M., White, H. L., Tang, F. L. M., Russell, A. & Harfenist, M. (1986). Drug Dev. Res. 9, 171–188.
  3. Oxford Diffraction (2010). CrysAlis PRO Oxford Diffraction Ltd, Yarnton, England.
  4. Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [DOI] [PubMed]
  5. Shoeb, A., Anwer, F., Kapil, R. S., Popli, S. P., Dua, P. & Dhawan, B. N. (1973). J. Med. Chem. 16, 425–427. [DOI] [PubMed]
  6. Spek, A. L. (2009). Acta Cryst. D65, 148–155. [DOI] [PMC free article] [PubMed]

Associated Data

This section collects any data citations, data availability statements, or supplementary materials included in this article.

Supplementary Materials

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811023890/ya2140sup1.cif

e-67-o1799-sup1.cif (31.4KB, cif)

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811023890/ya2140Isup2.hkl

e-67-o1799-Isup2.hkl (168.6KB, hkl)

Supplementary material file. DOI: 10.1107/S1600536811023890/ya2140Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography

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