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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.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536811023890/ya2140sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536811023890/ya2140Isup2.hkl
Contains datablock I

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S1600536811023890/ya2140Isup3.cml
Supplementary material

CCDC reference: 834448

Key indicators

  • Single-crystal X-ray study
  • T = 295 K
  • Mean [sigma](C-C) = 0.010 Å
  • R factor = 0.080
  • wR factor = 0.246
  • Data-to-parameter ratio = 7.5

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT340_ALERT_3_B Low Bond Precision on C-C Bonds (x 1000) Ang .. 11
Alert level C PLAT089_ALERT_3_C Poor Data / Parameter Ratio (Zmax .LT. 18) ..... 7.45 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for N3A PLAT334_ALERT_2_C Small Average Benzene C-C Dist. C31A -C36A 1.37 Ang. PLAT910_ALERT_3_C Missing # of FCF Reflections Below Th(Min) ..... 2 PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L= 0.600 7 PLAT912_ALERT_4_C Missing # of FCF Reflections Above STh/L= 0.600 92
Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 73.60 From the CIF: _reflns_number_total 3509 Count of symmetry unique reflns 3613 Completeness (_total/calc) 97.12% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 0 Fraction of Friedel pairs measured 0.000 Are heavy atom types Z>Si present no PLAT072_ALERT_2_G SHELXL First Parameter in WGHT Unusually Large. 0.13
0 ALERT level A = Most likely a serious problem - resolve or explain 1 ALERT level B = A potentially serious problem, consider carefully 6 ALERT level C = Check. Ensure it is not caused by an omission or oversight 2 ALERT level G = General information/check it is not something unexpected 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 3 ALERT type 2 Indicator that the structure model may be wrong or deficient 4 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Comment top

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.

Related literature top

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).

Experimental top

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 top

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.

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: 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 (Spek, 2009).

Figures top
[Figure 1] Fig. 1. Asymmetric unit of the title compound; displacement ellipsoids are drawn at the 30% probability level. H atoms were omitted for clarity.
9-Ethyl-N-(3-nitrobenzylidene)-9H-carbazol-3-amine top
Crystal data top
C21H17N3O2F(000) = 720
Mr = 343.38Dx = 1.331 Mg m3
Monoclinic, P21Melting point: 352 K
Hall symbol: P 2ybCu Kα radiation, λ = 1.54184 Å
a = 8.1550 (4) ÅCell parameters from 2308 reflections
b = 13.5093 (7) Åθ = 5.6–73.4°
c = 16.0248 (9) ŵ = 0.71 mm1
β = 103.899 (5)°T = 295 K
V = 1713.74 (16) Å3Block, pale-orange
Z = 40.44 × 0.41 × 0.35 mm
Data collection top
Oxford Diffraction Xcalibur Ruby Gemini
diffractometer
3509 independent reflections
Radiation source: Enhance (Cu) X-ray Source2458 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.034
Detector resolution: 10.5081 pixels mm-1θmax = 73.6°, θmin = 5.6°
ω scansh = 107
Absorption correction: multi-scan
(CrysAlis PRO; Oxford Diffraction, 2010)
k = 169
Tmin = 0.830, Tmax = 1.000l = 1918
6983 measured reflections
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)] = 0.080Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.246H-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 parametersΔρmax = 0.32 e Å3
1 restraintΔρmin = 0.29 e Å3
Crystal data top
C21H17N3O2V = 1713.74 (16) Å3
Mr = 343.38Z = 4
Monoclinic, P21Cu Kα radiation
a = 8.1550 (4) ŵ = 0.71 mm1
b = 13.5093 (7) ÅT = 295 K
c = 16.0248 (9) Å0.44 × 0.41 × 0.35 mm
β = 103.899 (5)°
Data collection top
Oxford Diffraction Xcalibur Ruby Gemini
diffractometer
3509 independent reflections
Absorption correction: multi-scan
(CrysAlis PRO; Oxford Diffraction, 2010)
2458 reflections with I > 2σ(I)
Tmin = 0.830, Tmax = 1.000Rint = 0.034
6983 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0801 restraint
wR(F2) = 0.246H-atom parameters constrained
S = 1.08Δρmax = 0.32 e Å3
3509 reflectionsΔρmin = 0.29 e Å3
471 parameters
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O1A0.0282 (8)0.1393 (7)0.4830 (4)0.105 (3)
O2A0.1202 (9)0.1178 (9)0.6087 (4)0.140 (4)
N3A0.1053 (9)0.1305 (6)0.5327 (4)0.082 (3)
N12A0.1520 (8)0.1142 (5)0.1190 (3)0.068 (2)
N14A0.2402 (7)0.1332 (5)0.2351 (3)0.0687 (19)
C1A0.3254 (9)0.0611 (6)0.0235 (4)0.072 (3)
C2A0.3430 (9)0.0681 (6)0.1102 (5)0.068 (2)
C3A0.2341 (9)0.1275 (6)0.1455 (4)0.066 (2)
C4A0.1066 (8)0.1804 (6)0.0897 (4)0.064 (2)
C5A0.0895 (8)0.1752 (5)0.0019 (4)0.059 (2)
C6A0.0291 (8)0.2176 (5)0.0709 (4)0.061 (2)
C7A0.1635 (9)0.2809 (7)0.0821 (5)0.074 (3)
C8A0.2614 (10)0.3017 (7)0.1638 (5)0.079 (3)
C9A0.2195 (10)0.2607 (7)0.2351 (5)0.079 (3)
C10A0.0813 (10)0.1994 (6)0.2275 (4)0.068 (3)
C11A0.0148 (9)0.1772 (6)0.1449 (5)0.067 (2)
C13A0.1988 (8)0.1136 (5)0.0308 (4)0.063 (2)
C15A0.3788 (9)0.1236 (6)0.2892 (4)0.069 (3)
C16A0.2434 (11)0.0668 (7)0.1766 (5)0.077 (3)
C17A0.3884 (10)0.1283 (8)0.1880 (5)0.086 (3)
C31A0.3893 (8)0.1261 (6)0.3828 (4)0.066 (2)
C32A0.2451 (9)0.1300 (6)0.4137 (4)0.066 (2)
C33A0.2603 (9)0.1313 (6)0.5004 (5)0.070 (2)
C34A0.4152 (11)0.1297 (7)0.5583 (5)0.083 (3)
C35A0.5585 (10)0.1295 (8)0.5269 (5)0.083 (3)
C36A0.5457 (9)0.1265 (7)0.4407 (5)0.075 (3)
O1B0.4490 (7)0.8842 (5)0.4146 (4)0.093 (2)
O2B0.6022 (9)0.8772 (6)0.5430 (4)0.105 (3)
N3B0.5850 (9)0.8824 (5)0.4656 (4)0.079 (2)
N12B0.6177 (7)0.9094 (5)0.1890 (3)0.0683 (19)
N14B0.7154 (7)0.8953 (5)0.1660 (4)0.068 (2)
C1B0.7939 (10)0.9677 (6)0.0465 (5)0.076 (3)
C2B0.8102 (9)0.9611 (7)0.0408 (4)0.070 (3)
C3B0.7059 (8)0.8992 (6)0.0763 (4)0.063 (2)
C4B0.5824 (8)0.8446 (5)0.0241 (4)0.061 (2)
C5B0.5615 (8)0.8491 (5)0.0652 (4)0.060 (2)
C6B0.4411 (8)0.8060 (6)0.1376 (4)0.066 (3)
C7B0.3071 (9)0.7411 (7)0.1470 (5)0.072 (3)
C8B0.2099 (10)0.7211 (8)0.2275 (5)0.084 (3)
C9B0.2454 (10)0.7646 (7)0.3004 (5)0.083 (3)
C10B0.3792 (10)0.8263 (7)0.2938 (4)0.078 (3)
C11B0.4788 (9)0.8478 (5)0.2124 (4)0.063 (2)
C13B0.6670 (9)0.9118 (6)0.0994 (4)0.065 (2)
C15B0.8523 (9)0.9092 (6)0.2203 (4)0.069 (3)
C16B0.7073 (11)0.9593 (6)0.2463 (5)0.076 (3)
C17B0.8592 (11)0.9026 (8)0.2563 (6)0.093 (3)
C31B0.8645 (9)0.9048 (6)0.3131 (5)0.067 (2)
C32B0.7214 (9)0.8965 (6)0.3455 (4)0.068 (2)
C33B0.7393 (9)0.8892 (6)0.4328 (4)0.069 (2)
C34B0.8935 (10)0.8861 (7)0.4902 (5)0.077 (3)
C35B1.0380 (10)0.8944 (8)0.4593 (5)0.082 (3)
C36B1.0220 (9)0.9035 (7)0.3711 (5)0.075 (3)
H1A0.398120.021420.001400.0854*
H2A0.428710.032770.146950.0816*
H4A0.032720.219360.111610.0771*
H7A0.189620.310350.034460.0883*
H8A0.354750.343150.170580.0944*
H9A0.286280.274740.289520.0952*
H10A0.052860.173560.275900.0819*
H15A0.476910.114830.270220.0823*
H16A0.166310.055860.232120.0923*
H16B0.284900.002850.153170.0923*
H17A0.348010.192110.210200.1293*
H17B0.442590.096130.227620.1293*
H17C0.468040.136250.133580.1293*
H32A0.138940.131710.375830.0799*
H34A0.423080.128680.617170.0991*
H35A0.664460.131480.564850.1003*
H36A0.643320.124690.420320.0896*
H1B0.864861.007890.069210.0910*
H2B0.892690.998620.077470.0833*
H4B0.512350.804480.047610.0734*
H7B0.283060.711250.098970.0861*
H8B0.118900.677950.233840.1009*
H9B0.176070.750970.354280.0997*
H10B0.403790.853560.342700.0944*
H15B0.949040.922600.201200.0821*
H16C0.742541.024410.223400.0911*
H16D0.630740.967910.302290.0911*
H17D0.942560.901990.202600.1391*
H17E0.905510.933500.299480.1391*
H17F0.826950.835810.273270.1391*
H32B0.614430.895880.308420.0811*
H34B0.901320.878660.548670.0927*
H35B1.144300.893860.497030.0978*
H36B1.118890.908750.350450.0896*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O1A0.083 (4)0.151 (6)0.090 (4)0.013 (4)0.037 (3)0.013 (4)
O2A0.117 (5)0.254 (11)0.058 (3)0.014 (6)0.039 (3)0.011 (5)
N3A0.088 (4)0.101 (5)0.059 (4)0.005 (4)0.023 (3)0.001 (3)
N12A0.081 (4)0.075 (4)0.052 (3)0.007 (3)0.026 (3)0.001 (3)
N14A0.068 (3)0.089 (4)0.052 (3)0.003 (3)0.020 (3)0.003 (3)
C1A0.077 (4)0.073 (4)0.071 (5)0.014 (4)0.030 (3)0.004 (4)
C2A0.067 (4)0.067 (4)0.071 (4)0.012 (3)0.018 (3)0.005 (3)
C3A0.065 (4)0.077 (4)0.060 (4)0.006 (4)0.025 (3)0.003 (4)
C4A0.061 (3)0.076 (4)0.061 (4)0.001 (3)0.024 (3)0.002 (3)
C5A0.054 (3)0.071 (4)0.055 (4)0.005 (3)0.019 (3)0.003 (3)
C6A0.053 (3)0.071 (4)0.062 (4)0.009 (3)0.019 (3)0.001 (3)
C7A0.068 (4)0.088 (5)0.066 (4)0.003 (4)0.019 (3)0.007 (4)
C8A0.071 (4)0.092 (5)0.073 (5)0.006 (4)0.017 (3)0.009 (4)
C9A0.072 (4)0.095 (6)0.070 (5)0.002 (4)0.015 (4)0.018 (4)
C10A0.080 (4)0.076 (5)0.051 (4)0.005 (4)0.020 (3)0.003 (3)
C11A0.072 (4)0.072 (4)0.062 (4)0.015 (4)0.026 (3)0.000 (3)
C13A0.063 (4)0.064 (4)0.065 (4)0.003 (3)0.021 (3)0.003 (3)
C15A0.060 (4)0.084 (5)0.066 (4)0.002 (4)0.023 (3)0.002 (4)
C16A0.087 (5)0.081 (5)0.070 (5)0.014 (4)0.033 (4)0.008 (4)
C17A0.090 (5)0.100 (6)0.079 (5)0.009 (5)0.041 (4)0.003 (5)
C31A0.066 (4)0.073 (4)0.060 (4)0.000 (4)0.020 (3)0.003 (3)
C32A0.065 (4)0.076 (4)0.055 (4)0.000 (4)0.009 (3)0.004 (3)
C33A0.071 (4)0.077 (4)0.066 (4)0.009 (4)0.025 (3)0.005 (4)
C34A0.097 (5)0.099 (6)0.051 (4)0.007 (5)0.015 (4)0.004 (4)
C35A0.078 (4)0.102 (6)0.064 (4)0.004 (5)0.005 (3)0.004 (4)
C36A0.067 (4)0.086 (5)0.071 (4)0.002 (4)0.017 (3)0.006 (4)
O1B0.071 (3)0.120 (5)0.088 (4)0.006 (3)0.022 (3)0.009 (4)
O2B0.120 (5)0.140 (6)0.066 (4)0.005 (4)0.043 (3)0.001 (3)
N3B0.086 (4)0.088 (4)0.069 (4)0.010 (4)0.030 (3)0.006 (3)
N12B0.076 (3)0.079 (4)0.055 (3)0.005 (3)0.026 (3)0.000 (3)
N14B0.065 (3)0.076 (4)0.064 (4)0.002 (3)0.020 (3)0.001 (3)
C1B0.080 (4)0.081 (5)0.070 (4)0.014 (4)0.024 (4)0.002 (4)
C2B0.070 (4)0.084 (5)0.054 (4)0.011 (4)0.014 (3)0.005 (3)
C3B0.056 (3)0.076 (4)0.057 (4)0.003 (3)0.015 (3)0.002 (3)
C4B0.060 (3)0.066 (4)0.057 (4)0.000 (3)0.012 (3)0.001 (3)
C5B0.065 (4)0.057 (3)0.059 (4)0.005 (3)0.018 (3)0.001 (3)
C6B0.062 (4)0.083 (5)0.056 (4)0.006 (3)0.023 (3)0.005 (3)
C7B0.070 (4)0.087 (5)0.061 (4)0.006 (4)0.021 (3)0.007 (4)
C8B0.068 (4)0.104 (6)0.083 (5)0.007 (4)0.024 (4)0.011 (5)
C9B0.074 (4)0.115 (7)0.060 (4)0.005 (5)0.015 (3)0.010 (4)
C10B0.077 (4)0.107 (6)0.053 (4)0.006 (4)0.019 (3)0.008 (4)
C11B0.069 (4)0.071 (4)0.051 (3)0.006 (3)0.019 (3)0.003 (3)
C13B0.072 (4)0.071 (4)0.055 (4)0.005 (3)0.020 (3)0.002 (3)
C15B0.066 (4)0.084 (5)0.057 (4)0.001 (4)0.018 (3)0.003 (3)
C16B0.098 (5)0.075 (4)0.060 (4)0.003 (4)0.029 (4)0.005 (3)
C17B0.102 (6)0.105 (6)0.084 (6)0.008 (5)0.048 (5)0.003 (5)
C31B0.063 (4)0.076 (4)0.061 (4)0.001 (4)0.014 (3)0.004 (4)
C32B0.071 (4)0.075 (4)0.056 (4)0.004 (4)0.013 (3)0.004 (3)
C33B0.069 (4)0.075 (4)0.062 (4)0.001 (4)0.016 (3)0.005 (4)
C34B0.079 (5)0.092 (5)0.058 (4)0.005 (4)0.012 (3)0.004 (4)
C35B0.071 (4)0.103 (6)0.064 (4)0.002 (4)0.002 (3)0.010 (4)
C36B0.068 (4)0.090 (5)0.068 (4)0.007 (4)0.019 (3)0.007 (4)
Geometric parameters (Å, º) top
O1A—N3A1.190 (10)C16A—H16B0.9700
O2A—N3A1.207 (9)C17A—H17B0.9600
O1B—N3B1.210 (9)C17A—H17C0.9600
O2B—N3B1.216 (9)C17A—H17A0.9600
N3A—C33A1.477 (11)C32A—H32A0.9300
N12A—C13A1.373 (8)C34A—H34A0.9300
N12A—C11A1.388 (10)C35A—H35A0.9300
N12A—C16A1.466 (11)C36A—H36A0.9300
N14A—C15A1.255 (9)C1B—C2B1.376 (10)
N14A—C3A1.427 (8)C1B—C13B1.392 (11)
N3B—C33B1.479 (10)C2B—C3B1.407 (11)
N12B—C11B1.383 (9)C3B—C4B1.361 (10)
N12B—C13B1.395 (8)C4B—C5B1.401 (9)
N12B—C16B1.468 (10)C5B—C6B1.450 (9)
N14B—C3B1.422 (9)C5B—C13B1.409 (10)
N14B—C15B1.254 (9)C6B—C7B1.381 (11)
C1A—C13A1.376 (10)C6B—C11B1.424 (9)
C1A—C2A1.365 (10)C7B—C8B1.369 (11)
C2A—C3A1.412 (11)C8B—C9B1.399 (12)
C3A—C4A1.395 (10)C9B—C10B1.357 (12)
C4A—C5A1.382 (9)C10B—C11B1.392 (9)
C5A—C6A1.443 (9)C15B—C31B1.468 (10)
C5A—C13A1.409 (9)C16B—C17B1.497 (13)
C6A—C7A1.368 (11)C31B—C32B1.391 (11)
C6A—C11A1.427 (10)C31B—C36B1.393 (11)
C7A—C8A1.389 (11)C32B—C33B1.375 (9)
C8A—C9A1.384 (12)C33B—C34B1.369 (11)
C9A—C10A1.380 (12)C34B—C35B1.388 (12)
C10A—C11A1.399 (10)C35B—C36B1.393 (11)
C15A—C31A1.482 (9)C1B—H1B0.9300
C16A—C17A1.492 (13)C2B—H2B0.9300
C31A—C36A1.385 (10)C4B—H4B0.9300
C31A—C32A1.382 (10)C7B—H7B0.9300
C32A—C33A1.365 (10)C8B—H8B0.9300
C33A—C34A1.376 (12)C9B—H9B0.9300
C34A—C35A1.379 (12)C10B—H10B0.9300
C35A—C36A1.361 (11)C15B—H15B0.9300
C1A—H1A0.9300C16B—H16C0.9700
C2A—H2A0.9300C16B—H16D0.9700
C4A—H4A0.9300C17B—H17D0.9600
C7A—H7A0.9300C17B—H17E0.9600
C8A—H8A0.9300C17B—H17F0.9600
C9A—H9A0.9300C32B—H32B0.9300
C10A—H10A0.9300C34B—H34B0.9300
C15A—H15A0.9300C35B—H35B0.9300
C16A—H16A0.9700C36B—H36B0.9300
O1A—N3A—O2A122.9 (8)C33A—C32A—H32A120.00
O1A—N3A—C33A119.2 (6)C33A—C34A—H34A121.00
O2A—N3A—C33A117.9 (7)C35A—C34A—H34A121.00
C11A—N12A—C13A108.4 (6)C34A—C35A—H35A120.00
C11A—N12A—C16A125.1 (6)C36A—C35A—H35A120.00
C13A—N12A—C16A126.0 (6)C31A—C36A—H36A120.00
C3A—N14A—C15A119.8 (6)C35A—C36A—H36A120.00
O1B—N3B—C33B118.6 (6)C2B—C1B—C13B117.4 (7)
O2B—N3B—C33B117.8 (7)C1B—C2B—C3B122.0 (7)
O1B—N3B—O2B123.5 (8)N14B—C3B—C2B122.7 (6)
C11B—N12B—C13B107.9 (6)N14B—C3B—C4B117.0 (6)
C13B—N12B—C16B124.7 (6)C2B—C3B—C4B120.2 (6)
C11B—N12B—C16B127.3 (5)C3B—C4B—C5B119.6 (6)
C3B—N14B—C15B121.3 (6)C4B—C5B—C6B133.9 (6)
C2A—C1A—C13A119.2 (7)C4B—C5B—C13B119.2 (6)
C1A—C2A—C3A121.6 (7)C6B—C5B—C13B106.8 (6)
N14A—C3A—C2A124.1 (7)C5B—C6B—C7B135.1 (6)
N14A—C3A—C4A117.3 (6)C5B—C6B—C11B105.8 (6)
C2A—C3A—C4A118.6 (6)C7B—C6B—C11B119.0 (6)
C3A—C4A—C5A120.3 (6)C6B—C7B—C8B119.5 (7)
C4A—C5A—C6A133.4 (6)C7B—C8B—C9B121.0 (8)
C4A—C5A—C13A119.4 (6)C8B—C9B—C10B121.1 (7)
C6A—C5A—C13A107.1 (5)C9B—C10B—C11B118.6 (7)
C7A—C6A—C11A118.9 (6)N12B—C11B—C6B109.8 (5)
C5A—C6A—C11A105.5 (6)N12B—C11B—C10B129.5 (6)
C5A—C6A—C7A135.6 (6)C6B—C11B—C10B120.7 (7)
C6A—C7A—C8A120.8 (7)N12B—C13B—C1B128.9 (7)
C7A—C8A—C9A119.8 (8)N12B—C13B—C5B109.5 (6)
C8A—C9A—C10A121.7 (7)C1B—C13B—C5B121.6 (6)
C9A—C10A—C11A118.2 (7)N14B—C15B—C31B122.0 (7)
N12A—C11A—C6A109.4 (6)N12B—C16B—C17B112.4 (7)
N12A—C11A—C10A130.0 (7)C15B—C31B—C32B121.5 (7)
C6A—C11A—C10A120.6 (7)C15B—C31B—C36B120.3 (7)
N12A—C13A—C1A129.4 (6)C32B—C31B—C36B118.1 (7)
N12A—C13A—C5A109.6 (6)C31B—C32B—C33B119.5 (7)
C1A—C13A—C5A121.0 (6)N3B—C33B—C32B118.4 (6)
N14A—C15A—C31A121.4 (6)N3B—C33B—C34B118.8 (6)
N12A—C16A—C17A111.8 (7)C32B—C33B—C34B122.8 (7)
C15A—C31A—C36A119.9 (6)C33B—C34B—C35B118.7 (7)
C15A—C31A—C32A121.1 (6)C34B—C35B—C36B119.2 (7)
C32A—C31A—C36A119.1 (6)C31B—C36B—C35B121.6 (7)
C31A—C32A—C33A119.2 (7)C2B—C1B—H1B121.00
C32A—C33A—C34A122.0 (7)C13B—C1B—H1B121.00
N3A—C33A—C32A118.7 (7)C1B—C2B—H2B119.00
N3A—C33A—C34A119.2 (7)C3B—C2B—H2B119.00
C33A—C34A—C35A118.4 (7)C3B—C4B—H4B120.00
C34A—C35A—C36A120.4 (7)C5B—C4B—H4B120.00
C31A—C36A—C35A120.9 (7)C6B—C7B—H7B120.00
C2A—C1A—H1A120.00C8B—C7B—H7B120.00
C13A—C1A—H1A120.00C7B—C8B—H8B120.00
C1A—C2A—H2A119.00C9B—C8B—H8B119.00
C3A—C2A—H2A119.00C8B—C9B—H9B119.00
C5A—C4A—H4A120.00C10B—C9B—H9B119.00
C3A—C4A—H4A120.00C9B—C10B—H10B121.00
C6A—C7A—H7A120.00C11B—C10B—H10B121.00
C8A—C7A—H7A120.00N14B—C15B—H15B119.00
C9A—C8A—H8A120.00C31B—C15B—H15B119.00
C7A—C8A—H8A120.00N12B—C16B—H16C109.00
C8A—C9A—H9A119.00N12B—C16B—H16D109.00
C10A—C9A—H9A119.00C17B—C16B—H16C109.00
C9A—C10A—H10A121.00C17B—C16B—H16D109.00
C11A—C10A—H10A121.00H16C—C16B—H16D108.00
N14A—C15A—H15A119.00C16B—C17B—H17D110.00
C31A—C15A—H15A119.00C16B—C17B—H17E109.00
N12A—C16A—H16A109.00C16B—C17B—H17F109.00
N12A—C16A—H16B109.00H17D—C17B—H17E109.00
C17A—C16A—H16A109.00H17D—C17B—H17F109.00
C17A—C16A—H16B109.00H17E—C17B—H17F109.00
H16A—C16A—H16B108.00C31B—C32B—H32B120.00
H17B—C17A—H17C109.00C33B—C32B—H32B120.00
C16A—C17A—H17A110.00C33B—C34B—H34B121.00
C16A—C17A—H17B109.00C35B—C34B—H34B121.00
C16A—C17A—H17C110.00C34B—C35B—H35B120.00
H17A—C17A—H17B109.00C36B—C35B—H35B120.00
H17A—C17A—H17C109.00C31B—C36B—H36B119.00
C31A—C32A—H32A120.00C35B—C36B—H36B119.00
O1A—N3A—C33A—C32A7.9 (13)C6A—C7A—C8A—C9A2.2 (13)
O1A—N3A—C33A—C34A174.5 (9)C7A—C8A—C9A—C10A0.3 (14)
O2A—N3A—C33A—C32A169.9 (10)C8A—C9A—C10A—C11A1.6 (13)
O2A—N3A—C33A—C34A7.8 (13)C9A—C10A—C11A—N12A175.9 (8)
C13A—N12A—C11A—C6A0.6 (8)C9A—C10A—C11A—C6A0.4 (12)
C13A—N12A—C11A—C10A177.3 (8)N14A—C15A—C31A—C36A172.7 (8)
C16A—N12A—C11A—C6A173.6 (7)N14A—C15A—C31A—C32A6.0 (12)
C16A—N12A—C11A—C10A9.8 (13)C15A—C31A—C36A—C35A179.5 (9)
C11A—N12A—C13A—C1A178.7 (8)C15A—C31A—C32A—C33A179.4 (8)
C11A—N12A—C13A—C5A1.2 (8)C36A—C31A—C32A—C33A1.9 (12)
C16A—N12A—C13A—C1A8.5 (13)C32A—C31A—C36A—C35A0.8 (14)
C16A—N12A—C13A—C5A174.0 (7)C31A—C32A—C33A—C34A0.6 (13)
C11A—N12A—C16A—C17A91.1 (9)C31A—C32A—C33A—N3A177.0 (7)
C13A—N12A—C16A—C17A80.7 (10)N3A—C33A—C34A—C35A179.4 (8)
C15A—N14A—C3A—C2A32.0 (12)C32A—C33A—C34A—C35A1.8 (14)
C15A—N14A—C3A—C4A151.4 (8)C33A—C34A—C35A—C36A2.9 (15)
C3A—N14A—C15A—C31A178.2 (7)C34A—C35A—C36A—C31A1.6 (15)
O1B—N3B—C33B—C34B179.3 (8)C13B—C1B—C2B—C3B1.2 (12)
O2B—N3B—C33B—C32B179.1 (8)C2B—C1B—C13B—N12B175.9 (8)
O1B—N3B—C33B—C32B0.5 (11)C2B—C1B—C13B—C5B1.4 (12)
O2B—N3B—C33B—C34B2.1 (12)C1B—C2B—C3B—N14B176.7 (8)
C16B—N12B—C11B—C6B173.7 (7)C1B—C2B—C3B—C4B1.1 (12)
C16B—N12B—C11B—C10B7.8 (13)N14B—C3B—C4B—C5B177.0 (6)
C11B—N12B—C16B—C17B96.0 (9)C2B—C3B—C4B—C5B1.1 (11)
C13B—N12B—C16B—C17B79.7 (9)C3B—C4B—C5B—C6B176.4 (8)
C16B—N12B—C13B—C1B7.6 (13)C3B—C4B—C5B—C13B1.3 (10)
C11B—N12B—C13B—C1B176.0 (8)C4B—C5B—C6B—C7B3.7 (15)
C11B—N12B—C13B—C5B1.6 (8)C4B—C5B—C6B—C11B174.1 (7)
C13B—N12B—C11B—C10B176.0 (8)C13B—C5B—C6B—C7B179.3 (9)
C16B—N12B—C13B—C5B174.8 (7)C13B—C5B—C6B—C11B1.5 (8)
C13B—N12B—C11B—C6B2.6 (8)C4B—C5B—C13B—N12B176.4 (6)
C15B—N14B—C3B—C2B31.6 (12)C4B—C5B—C13B—C1B1.4 (11)
C3B—N14B—C15B—C31B179.6 (7)C6B—C5B—C13B—N12B0.0 (8)
C15B—N14B—C3B—C4B152.6 (8)C6B—C5B—C13B—C1B177.8 (7)
C2A—C1A—C13A—N12A176.3 (7)C5B—C6B—C7B—C8B175.2 (9)
C13A—C1A—C2A—C3A0.3 (12)C11B—C6B—C7B—C8B2.3 (12)
C2A—C1A—C13A—C5A0.9 (11)C5B—C6B—C11B—N12B2.5 (8)
C1A—C2A—C3A—C4A0.4 (12)C5B—C6B—C11B—C10B176.2 (7)
C1A—C2A—C3A—N14A176.2 (7)C7B—C6B—C11B—N12B179.3 (7)
N14A—C3A—C4A—C5A177.6 (7)C7B—C6B—C11B—C10B2.0 (11)
C2A—C3A—C4A—C5A0.7 (11)C6B—C7B—C8B—C9B0.7 (14)
C3A—C4A—C5A—C13A1.9 (11)C7B—C8B—C9B—C10B1.4 (15)
C3A—C4A—C5A—C6A177.9 (7)C8B—C9B—C10B—C11B1.7 (14)
C4A—C5A—C6A—C11A175.5 (8)C9B—C10B—C11B—N12B178.4 (8)
C13A—C5A—C6A—C7A179.5 (9)C9B—C10B—C11B—C6B0.0 (12)
C13A—C5A—C6A—C11A0.8 (8)N14B—C15B—C31B—C32B7.7 (13)
C4A—C5A—C13A—N12A175.7 (6)N14B—C15B—C31B—C36B168.9 (8)
C4A—C5A—C13A—C1A2.1 (10)C15B—C31B—C32B—C33B177.8 (8)
C6A—C5A—C13A—N12A1.3 (8)C36B—C31B—C32B—C33B1.2 (12)
C6A—C5A—C13A—C1A179.0 (7)C15B—C31B—C36B—C35B176.8 (9)
C4A—C5A—C6A—C7A3.1 (15)C32B—C31B—C36B—C35B0.1 (13)
C11A—C6A—C7A—C8A3.3 (12)C31B—C32B—C33B—N3B178.8 (7)
C5A—C6A—C11A—N12A0.2 (8)C31B—C32B—C33B—C34B2.4 (13)
C5A—C6A—C11A—C10A176.9 (7)N3B—C33B—C34B—C35B178.8 (8)
C7A—C6A—C11A—N12A179.1 (7)C32B—C33B—C34B—C35B2.5 (14)
C7A—C6A—C11A—C10A2.1 (11)C33B—C34B—C35B—C36B1.3 (15)
C5A—C6A—C7A—C8A175.2 (8)C34B—C35B—C36B—C31B0.2 (15)

Experimental details

Crystal data
Chemical formulaC21H17N3O2
Mr343.38
Crystal system, space groupMonoclinic, P21
Temperature (K)295
a, b, c (Å)8.1550 (4), 13.5093 (7), 16.0248 (9)
β (°) 103.899 (5)
V3)1713.74 (16)
Z4
Radiation typeCu Kα
µ (mm1)0.71
Crystal size (mm)0.44 × 0.41 × 0.35
Data collection
DiffractometerOxford Diffraction Xcalibur Ruby Gemini
diffractometer
Absorption correctionMulti-scan
(CrysAlis PRO; Oxford Diffraction, 2010)
Tmin, Tmax0.830, 1.000
No. of measured, independent and
observed [I > 2σ(I)] reflections
6983, 3509, 2458
Rint0.034
(sin θ/λ)max1)0.622
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.080, 0.246, 1.08
No. of reflections3509
No. of parameters471
No. of restraints1
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.32, 0.29

Computer programs: CrysAlis PRO (Oxford Diffraction, 2010), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009).

 

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