(±)-4a-(4-Nitro-benz-yl)-2,3,4,4a-tetra-hydro-1H-carbazole.

The title mol-ecule, C(19)H(18)N(2)O(2), is built up from three fused rings, viz. phenyl, pyrrole and cyclo-hexane, linked to a nitro-benzyl group. The C atom bearing the nitro-benzyl group is chiral and the compound is a racemate (R/S). The dihedral angle between the nitro-benzyl and indole rings is 57.49 (5)°. The cyclo-hexane ring adopts a slightly distorted chair conformation.

Related literature

For the biocativity of carbazole derivatives, see: Nakahara et al. (2002 ▶); Yukari et al. (2001 ▶, 2003 ▶). For crystallographic studies of carbazole derivatives, see: Gunaseelan et al. (2007 ▶); Murugavel et al. (2008 ▶).

Experimental

Crystal data

C19H18N2O2

M = 306.35

Monoclinic,

a = 8.7266 (3) Å

b = 16.6916 (6) Å

c = 11.0857 (4) Å

β = 105.790 (4)°

V = 1553.82 (10) Å3

Z = 4

Cu Kα radiation

μ = 0.69 mm−1

T = 295 K

0.5 × 0.4 × 0.3 mm

Data collection

Agilent Xcalibur Sapphire3 Gemini ultra diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010 ▶) T min = 0.967, T max = 1.000

4772 measured reflections

2479 independent reflections

2089 reflections with I > 2σ(I)

R int = 0.016

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.116

S = 1.04

2479 reflections

208 parameters

H-atom parameters constrained

Δρmax = 0.34 e Å−3

Δρmin = −0.27 e Å−3

Data collection: CrysAlis PRO (Agilent, 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: ORTEPIII (Burnett & Johnson, 1996 ▶) and ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811020277/dn2687sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811020277/dn2687Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811020277/dn2687Isup3.cml

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

C19H18N2O2	F(000) = 648
Mr = 306.35	Dx = 1.310 Mg m−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.5418 Å
a = 8.7266 (3) Å	Cell parameters from 2290 reflections
b = 16.6916 (6) Å	θ = 4.1–63.3°
c = 11.0857 (4) Å	µ = 0.69 mm−1
β = 105.790 (4)°	T = 295 K
V = 1553.82 (10) Å3	Block, colourless
Z = 4	0.5 × 0.4 × 0.3 mm

Agilent Xcalibur Sapphire3 Gemini ultra diffractometer	2479 independent reflections
Radiation source: Enhance Ultra (Cu) X-ray Source	2089 reflections with I > 2σ(I)
mirror	Rint = 0.016
Detector resolution: 16.0288 pixels mm-1	θmax = 63.4°, θmin = 4.9°
ω scans	h = −9→10
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	k = −19→15
Tmin = 0.967, Tmax = 1.000	l = −12→12
4772 measured reflections

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.116	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.053P)2 + 0.3423P] where P = (Fo2 + 2Fc2)/3
2479 reflections	(Δ/σ)max < 0.001
208 parameters	Δρmax = 0.34 e Å−3
0 restraints	Δρmin = −0.27 e Å−3

Experimental. Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm, CrysAlisPro (Agilent Technologies, 2010)

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

	x	y	z	Uiso*/Ueq
N1	−0.00300 (17)	0.11252 (9)	0.00877 (13)	0.0508 (4)
N2	−0.40823 (18)	−0.06469 (10)	0.32518 (16)	0.0606 (4)
O1	−0.45120 (19)	−0.11644 (11)	0.24495 (19)	0.0981 (6)
O2	−0.4868 (2)	−0.04523 (13)	0.39422 (19)	0.1103 (7)
C2	−0.26031 (19)	−0.02163 (10)	0.33128 (15)	0.0474 (4)
C4	−0.0688 (2)	0.26406 (11)	0.22420 (17)	0.0546 (5)
H4	−0.0133	0.2842	0.3020	0.066*
C5	−0.1638 (2)	−0.04885 (11)	0.26058 (16)	0.0522 (4)
H5	−0.1906	−0.0946	0.2115	0.063*
C6	0.01239 (19)	0.06249 (10)	0.33455 (14)	0.0447 (4)
C7	−0.0266 (2)	−0.00705 (11)	0.26372 (16)	0.0517 (4)
H7	0.0409	−0.0256	0.2178	0.062*
C8	−0.0060 (2)	0.20306 (10)	0.16888 (15)	0.0457 (4)
C9	0.14637 (19)	0.15610 (11)	0.21010 (15)	0.0465 (4)
C10	−0.2232 (2)	0.04547 (11)	0.40556 (16)	0.0512 (4)
H10	−0.2883	0.0621	0.4547	0.061*
C11	−0.0874 (2)	0.08749 (11)	0.40559 (15)	0.0490 (4)
H11	−0.0620	0.1335	0.4542	0.059*
C12	0.2623 (2)	0.05042 (12)	0.08696 (19)	0.0601 (5)
H12A	0.2364	0.0237	0.0063	0.072*
H12B	0.2832	0.0099	0.1521	0.072*
C13	−0.09041 (19)	0.17322 (10)	0.05232 (15)	0.0471 (4)
C14	0.1591 (2)	0.10996 (11)	0.33379 (15)	0.0503 (4)
H14A	0.2492	0.0737	0.3487	0.060*
H14B	0.1803	0.1480	0.4024	0.060*
C15	0.1269 (2)	0.10175 (10)	0.09656 (15)	0.0477 (4)
C16	0.2976 (2)	0.20659 (12)	0.22068 (19)	0.0603 (5)
H16A	0.2777	0.2442	0.1515	0.072*
H16B	0.3214	0.2372	0.2980	0.072*
C17	−0.2169 (2)	0.29487 (12)	0.1613 (2)	0.0623 (5)
H17	−0.2597	0.3370	0.1965	0.075*
C18	−0.3009 (2)	0.26371 (13)	0.04740 (19)	0.0636 (5)
H18	−0.4011	0.2842	0.0079	0.076*
C20	0.4094 (2)	0.10320 (15)	0.1016 (2)	0.0743 (6)
H20A	0.5013	0.0695	0.1060	0.089*
H20B	0.3941	0.1375	0.0286	0.089*
C22	−0.2390 (2)	0.20246 (13)	−0.00932 (17)	0.0588 (5)
H22	−0.2957	0.1817	−0.0864	0.071*
C23	0.4413 (2)	0.15502 (15)	0.2191 (2)	0.0717 (6)
H23A	0.4675	0.1208	0.2926	0.086*
H23B	0.5321	0.1894	0.2230	0.086*

	U11	U22	U33	U12	U13	U23
N1	0.0533 (8)	0.0569 (9)	0.0419 (7)	−0.0040 (7)	0.0123 (6)	−0.0011 (6)
N2	0.0532 (9)	0.0588 (10)	0.0678 (10)	−0.0018 (8)	0.0132 (8)	0.0018 (8)
O1	0.0780 (11)	0.0826 (11)	0.1356 (16)	−0.0255 (9)	0.0322 (10)	−0.0397 (11)
O2	0.0896 (12)	0.1405 (18)	0.1213 (14)	−0.0460 (12)	0.0636 (11)	−0.0443 (13)
C2	0.0457 (9)	0.0468 (9)	0.0473 (9)	0.0012 (7)	0.0087 (7)	0.0058 (8)
C4	0.0638 (11)	0.0508 (10)	0.0518 (10)	−0.0033 (9)	0.0201 (8)	−0.0001 (8)
C5	0.0608 (11)	0.0441 (10)	0.0511 (10)	−0.0018 (8)	0.0143 (8)	−0.0053 (8)
C6	0.0473 (9)	0.0479 (9)	0.0363 (8)	0.0040 (7)	0.0070 (7)	0.0062 (7)
C7	0.0590 (11)	0.0489 (10)	0.0510 (10)	0.0048 (8)	0.0214 (8)	−0.0013 (8)
C8	0.0490 (9)	0.0456 (9)	0.0435 (8)	−0.0043 (7)	0.0145 (7)	0.0031 (7)
C9	0.0444 (9)	0.0513 (10)	0.0426 (9)	−0.0050 (7)	0.0097 (7)	−0.0003 (7)
C10	0.0499 (10)	0.0577 (11)	0.0475 (9)	0.0047 (8)	0.0160 (8)	−0.0008 (8)
C11	0.0550 (10)	0.0481 (10)	0.0420 (8)	0.0014 (8)	0.0102 (7)	−0.0042 (7)
C12	0.0594 (11)	0.0656 (12)	0.0577 (11)	0.0043 (9)	0.0203 (9)	−0.0031 (9)
C13	0.0484 (9)	0.0517 (10)	0.0415 (9)	−0.0037 (8)	0.0124 (7)	0.0057 (7)
C14	0.0493 (9)	0.0576 (11)	0.0410 (9)	−0.0017 (8)	0.0070 (7)	0.0018 (8)
C15	0.0491 (9)	0.0507 (10)	0.0445 (9)	−0.0049 (8)	0.0151 (7)	0.0012 (7)
C16	0.0561 (11)	0.0632 (12)	0.0595 (11)	−0.0159 (9)	0.0121 (9)	−0.0002 (9)
C17	0.0689 (12)	0.0556 (11)	0.0716 (12)	0.0104 (9)	0.0346 (10)	0.0123 (10)
C18	0.0522 (11)	0.0729 (13)	0.0675 (12)	0.0094 (10)	0.0196 (9)	0.0230 (11)
C20	0.0561 (12)	0.0945 (16)	0.0787 (14)	0.0032 (11)	0.0295 (10)	0.0032 (12)
C22	0.0514 (10)	0.0734 (13)	0.0487 (10)	−0.0020 (9)	0.0090 (8)	0.0098 (9)
C23	0.0458 (10)	0.0912 (16)	0.0780 (14)	−0.0130 (10)	0.0165 (9)	0.0027 (12)

N1—C13	1.429 (2)	C10—C11	1.377 (2)
N1—C15	1.290 (2)	C11—H11	0.9300
C2—N2	1.463 (2)	C12—H12A	0.9700
C2—C5	1.375 (2)	C12—H12B	0.9700
C2—C10	1.376 (2)	C12—C15	1.487 (2)
N2—O1	1.223 (2)	C12—C20	1.529 (3)
N2—O2	1.203 (2)	C13—C22	1.380 (2)
C4—H4	0.9300	C14—H14A	0.9700
C4—C8	1.377 (2)	C14—H14B	0.9700
C4—C17	1.389 (3)	C16—H16A	0.9700
C5—H5	0.9300	C16—H16B	0.9700
C5—C7	1.378 (2)	C16—C23	1.525 (3)
C6—C7	1.391 (2)	C17—H17	0.9300
C6—C11	1.387 (2)	C17—C18	1.378 (3)
C6—C14	1.508 (2)	C18—H18	0.9300
C7—H7	0.9300	C18—C22	1.384 (3)
C8—C9	1.503 (2)	C20—H20A	0.9700
C8—C13	1.394 (2)	C20—H20B	0.9700
C9—C14	1.550 (2)	C20—C23	1.525 (3)
C9—C15	1.523 (2)	C22—H22	0.9300
C9—C16	1.543 (2)	C23—H23A	0.9700
C10—H10	0.9300	C23—H23B	0.9700
C15—N1—C13	106.51 (14)	C8—C13—N1	111.75 (15)
C5—C2—N2	118.76 (16)	C22—C13—N1	126.84 (16)
C5—C2—C10	121.97 (16)	C22—C13—C8	121.40 (17)
C10—C2—N2	119.26 (16)	C6—C14—C9	114.16 (13)
O1—N2—C2	118.20 (17)	C6—C14—H14A	108.7
O2—N2—C2	119.10 (17)	C6—C14—H14B	108.7
O2—N2—O1	122.58 (18)	C9—C14—H14A	108.7
C8—C4—H4	120.7	C9—C14—H14B	108.7
C8—C4—C17	118.61 (18)	H14A—C14—H14B	107.6
C17—C4—H4	120.7	N1—C15—C9	114.72 (15)
C2—C5—H5	120.6	N1—C15—C12	125.36 (16)
C2—C5—C7	118.76 (16)	C12—C15—C9	119.35 (15)
C7—C5—H5	120.6	C9—C16—H16A	109.1
C7—C6—C14	120.87 (15)	C9—C16—H16B	109.1
C11—C6—C7	118.46 (16)	H16A—C16—H16B	107.9
C11—C6—C14	120.67 (15)	C23—C16—C9	112.31 (17)
C5—C7—C6	120.96 (16)	C23—C16—H16A	109.1
C5—C7—H7	119.5	C23—C16—H16B	109.1
C6—C7—H7	119.5	C4—C17—H17	119.7
C4—C8—C9	132.56 (16)	C18—C17—C4	120.70 (19)
C4—C8—C13	120.21 (16)	C18—C17—H17	119.7
C13—C8—C9	107.22 (14)	C17—C18—H18	119.4
C8—C9—C14	111.88 (13)	C17—C18—C22	121.25 (18)
C8—C9—C15	99.71 (13)	C22—C18—H18	119.4
C8—C9—C16	113.94 (15)	C12—C20—H20A	109.3
C15—C9—C14	113.58 (14)	C12—C20—H20B	109.3
C15—C9—C16	106.80 (14)	H20A—C20—H20B	107.9
C16—C9—C14	110.48 (13)	C23—C20—C12	111.70 (16)
C2—C10—H10	120.7	C23—C20—H20A	109.3
C2—C10—C11	118.51 (16)	C23—C20—H20B	109.3
C11—C10—H10	120.7	C13—C22—C18	117.80 (18)
C6—C11—H11	119.4	C13—C22—H22	121.1
C10—C11—C6	121.29 (16)	C18—C22—H22	121.1
C10—C11—H11	119.4	C16—C23—C20	111.76 (16)
H12A—C12—H12B	108.3	C16—C23—H23A	109.3
C15—C12—H12A	109.9	C16—C23—H23B	109.3
C15—C12—H12B	109.9	C20—C23—H23A	109.3
C15—C12—C20	108.74 (17)	C20—C23—H23B	109.3
C20—C12—H12A	109.9	H23A—C23—H23B	107.9
C20—C12—H12B	109.9