2,3,4,9-Tetra-hydro-1H-carbazole.

In the title compound, C(12)H(13)N, two methyl-ene C atoms of the cyclo-hexene ring are disordered over two sites with occupancies of 0.591 (10) and 0.409 (10); both disorder components adopt half-chair conformations. The crystal structure is stabilized by inter-molecular N-H⋯π and C-H⋯π inter-actions.

Related literature

For a related structure, see: Arulmozhi et al. (2008 ▶). For general background, see: Mi et al. (2003 ▶); Hewlins et al. (1984 ▶); Mohanakrishnan & Srinivasan (1995a ▶,b ▶); Kansal & Potier (1986 ▶); Phillipson & Zenk (1980 ▶); Saxton (1983 ▶); Abraham (1975 ▶).

Experimental

Crystal data

C12H13N

M = 171.23

Orthorhombic,

a = 6.1067 (4) Å

b = 7.9488 (5) Å

c = 19.4512 (12) Å

V = 944.18 (10) Å3

Z = 4

Mo Kα radiation

μ = 0.07 mm−1

T = 293 (2) K

0.26 × 0.15 × 0.15 mm

Data collection

Bruker Kappa APEXII area-detector diffractometer

Absorption correction: none

13269 measured reflections

1777 independent reflections

1323 reflections with I > 2σ(I)

R int = 0.036

Refinement

R[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.123

S = 1.07

1777 reflections

137 parameters

15 restraints

H-atom parameters constrained

Δρmax = 0.14 e Å−3

Δρmin = −0.20 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2003 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808038713/ci2708sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808038713/ci2708Isup2.hkl

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

C12H13N	F000 = 368
Mr = 171.23	Dx = 1.205 Mg m−3
Orthorhombic, P212121	Mo Kα radiation λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 1778 reflections
a = 6.1067 (4) Å	θ = 2.1–31.1º
b = 7.9488 (5) Å	µ = 0.07 mm−1
c = 19.4512 (12) Å	T = 293 (2) K
V = 944.18 (10) Å3	Block, colourless
Z = 4	0.26 × 0.15 × 0.15 mm

Bruker Kappa APEXII area-detector diffractometer	1323 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.036
Monochromator: graphite	θmax = 31.1º
T = 293(2) K	θmin = 2.1º
ω and φ scans	h = −8→8
Absorption correction: none	k = −11→11
13269 measured reflections	l = −28→28
1777 independent reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.048	H-atom parameters constrained
wR(F2) = 0.123	w = 1/[σ2(Fo2) + (0.0603P)2 + 0.0496P] where P = (Fo2 + 2Fc2)/3
S = 1.07	(Δ/σ)max = 0.001
1777 reflections	Δρmax = 0.14 e Å−3
137 parameters	Δρmin = −0.20 e Å−3
15 restraints	Extinction correction: none
Primary atom site location: structure-invariant direct methods

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	Occ. (<1)
N1	0.7448 (2)	0.5987 (2)	0.95685 (8)	0.0547 (4)
H1A	0.8656	0.6513	0.9495	0.066*
C1	0.3210 (3)	0.4486 (2)	1.06567 (10)	0.0557 (5)
H1	0.1945	0.3846	1.0604	0.067*
C2	0.3803 (4)	0.5087 (3)	1.12920 (10)	0.0634 (5)
H2	0.2921	0.4854	1.1670	0.076*
C3	0.5689 (4)	0.6033 (3)	1.13826 (10)	0.0619 (5)
H3	0.6046	0.6419	1.1820	0.074*
C4	0.7035 (3)	0.6410 (2)	1.08415 (10)	0.0568 (5)
H4	0.8298	0.7045	1.0904	0.068*
C5	0.6448 (3)	0.5811 (2)	1.01954 (9)	0.0457 (4)
C6	0.4535 (3)	0.4849 (2)	1.00903 (9)	0.0429 (4)
C7	0.4433 (3)	0.4464 (2)	0.93742 (8)	0.0429 (4)
C8	0.6210 (3)	0.5184 (2)	0.90741 (9)	0.0473 (4)
C9	0.6730 (3)	0.5153 (3)	0.83301 (10)	0.0668 (6)
H9A	0.8252	0.4841	0.8267	0.080*	0.591 (10)
H9B	0.6521	0.6267	0.8138	0.080*	0.591 (10)
H9C	0.7893	0.4371	0.8240	0.080*	0.409 (10)
H9D	0.7193	0.6249	0.8182	0.080*	0.409 (10)
C10A	0.5287 (9)	0.3918 (9)	0.7958 (4)	0.0674 (15)	0.591 (10)
H10A	0.5876	0.2795	0.8019	0.101*	0.591 (10)
H10B	0.5318	0.4171	0.7470	0.101*	0.591 (10)
C11A	0.2927 (8)	0.3943 (9)	0.8204 (2)	0.0638 (13)	0.591 (10)
H11A	0.2083	0.3133	0.7941	0.096*	0.591 (10)
H11B	0.2308	0.5049	0.8122	0.096*	0.591 (10)
C10B	0.4709 (17)	0.4587 (13)	0.7953 (5)	0.076 (2)	0.409 (10)
H10C	0.3699	0.5527	0.7924	0.114*	0.409 (10)
H10D	0.5117	0.4282	0.7487	0.114*	0.409 (10)
C11B	0.3543 (15)	0.3125 (11)	0.8276 (3)	0.0651 (19)	0.409 (10)
H11C	0.2313	0.2806	0.7989	0.098*	0.409 (10)
H11D	0.4534	0.2173	0.8300	0.098*	0.409 (10)
C12	0.2741 (3)	0.3519 (3)	0.89757 (10)	0.0579 (5)
H12A	0.1293	0.3817	0.9141	0.069*	0.591 (10)
H12B	0.2943	0.2320	0.9043	0.069*	0.591 (10)
H12C	0.1428	0.4179	0.8941	0.069*	0.409 (10)
H12D	0.2390	0.2494	0.9212	0.069*	0.409 (10)

	U11	U22	U33	U12	U13	U23
N1	0.0455 (8)	0.0620 (9)	0.0565 (9)	−0.0161 (8)	0.0044 (7)	0.0019 (7)
C1	0.0518 (10)	0.0556 (11)	0.0597 (11)	−0.0079 (9)	0.0078 (9)	0.0039 (9)
C2	0.0707 (12)	0.0693 (12)	0.0502 (10)	0.0015 (12)	0.0120 (9)	0.0040 (9)
C3	0.0752 (13)	0.0599 (11)	0.0507 (11)	0.0054 (11)	−0.0054 (10)	−0.0048 (9)
C4	0.0577 (11)	0.0495 (10)	0.0631 (12)	−0.0038 (9)	−0.0095 (10)	−0.0022 (9)
C5	0.0447 (8)	0.0402 (8)	0.0522 (9)	−0.0020 (7)	−0.0005 (7)	0.0042 (7)
C6	0.0425 (8)	0.0374 (7)	0.0488 (8)	0.0012 (7)	0.0007 (7)	0.0036 (7)
C7	0.0422 (8)	0.0379 (8)	0.0487 (9)	0.0013 (7)	−0.0007 (7)	0.0010 (7)
C8	0.0440 (8)	0.0468 (9)	0.0511 (9)	0.0018 (8)	0.0023 (7)	0.0017 (8)
C9	0.0601 (11)	0.0876 (15)	0.0526 (10)	−0.0017 (12)	0.0084 (9)	0.0054 (11)
C10A	0.061 (3)	0.082 (4)	0.059 (2)	0.010 (3)	0.004 (2)	−0.007 (3)
C11A	0.057 (2)	0.076 (3)	0.058 (2)	0.003 (2)	−0.0071 (18)	−0.010 (2)
C10B	0.084 (6)	0.097 (6)	0.046 (3)	0.009 (5)	−0.008 (4)	−0.005 (4)
C11B	0.071 (4)	0.067 (4)	0.057 (3)	0.003 (4)	−0.011 (3)	−0.018 (3)
C12	0.0515 (10)	0.0590 (11)	0.0632 (11)	−0.0084 (9)	−0.0038 (9)	−0.0028 (9)

N1—C5	1.371 (2)	C9—H9B	0.97
N1—C8	1.379 (2)	C9—H9C	0.96
N1—H1A	0.86	C9—H9D	0.96
C1—C2	1.374 (3)	C10A—C11A	1.519 (7)
C1—C6	1.397 (2)	C10A—H10A	0.97
C1—H1	0.93	C10A—H10B	0.97
C2—C3	1.387 (3)	C11A—C12	1.542 (5)
C2—H2	0.93	C11A—H11A	0.97
C3—C4	1.369 (3)	C11A—H11B	0.97
C3—H3	0.93	C10B—C11B	1.501 (10)
C4—C5	1.391 (3)	C10B—H10C	0.97
C4—H4	0.93	C10B—H10D	0.97
C5—C6	1.411 (2)	C11B—C12	1.480 (6)
C6—C7	1.427 (2)	C11B—H11C	0.97
C7—C8	1.359 (2)	C11B—H11D	0.97
C7—C12	1.494 (2)	C12—H12A	0.97
C8—C9	1.482 (3)	C12—H12B	0.97
C9—C10B	1.505 (9)	C12—H12C	0.96
C9—C10A	1.505 (6)	C12—H12D	0.96
C9—H9A	0.97
C5—N1—C8	109.19 (14)	H9C—C9—H9D	108.3
C5—N1—H1A	125.4	C9—C10A—C11A	113.3 (5)
C8—N1—H1A	125.4	C9—C10A—H10A	108.9
C2—C1—C6	118.99 (18)	C11A—C10A—H10A	108.9
C2—C1—H1	120.5	C9—C10A—H10B	108.9
C6—C1—H1	120.5	C11A—C10A—H10B	108.9
C1—C2—C3	121.49 (19)	H10A—C10A—H10B	107.7
C1—C2—H2	119.3	C10A—C11A—C12	112.0 (5)
C3—C2—H2	119.3	C10A—C11A—H11A	109.2
C4—C3—C2	121.30 (18)	C12—C11A—H11A	109.2
C4—C3—H3	119.3	C10A—C11A—H11B	109.2
C2—C3—H3	119.3	C12—C11A—H11B	109.2
C3—C4—C5	117.72 (18)	H11A—C11A—H11B	107.9
C3—C4—H4	121.1	C11B—C10B—C9	114.6 (7)
C5—C4—H4	121.1	C11B—C10B—H10C	108.6
N1—C5—C4	130.84 (17)	C9—C10B—H10C	108.6
N1—C5—C6	107.17 (15)	C11B—C10B—H10D	108.6
C4—C5—C6	121.99 (17)	C9—C10B—H10D	108.6
C1—C6—C5	118.50 (16)	H10C—C10B—H10D	107.6
C1—C6—C7	134.42 (16)	C12—C11B—C10B	112.2 (7)
C5—C6—C7	107.08 (15)	C12—C11B—H11C	109.2
C8—C7—C6	107.10 (14)	C10B—C11B—H11C	109.2
C8—C7—C12	122.77 (16)	C12—C11B—H11D	109.2
C6—C7—C12	130.10 (15)	C10B—C11B—H11D	109.2
C7—C8—N1	109.45 (15)	H11C—C11B—H11D	107.9
C7—C8—C9	125.70 (17)	C11B—C12—C7	110.8 (3)
N1—C8—C9	124.85 (17)	C7—C12—C11A	110.1 (2)
C8—C9—C10B	107.8 (4)	C11B—C12—H12A	131.1
C8—C9—C10A	110.8 (3)	C7—C12—H12A	109.6
C8—C9—H9A	109.5	C11A—C12—H12A	109.6
C10B—C9—H9A	130.4	C11B—C12—H12B	82.7
C10A—C9—H9A	109.5	C7—C12—H12B	109.6
C8—C9—H9B	109.5	C11A—C12—H12B	109.6
C10B—C9—H9B	88.7	H12A—C12—H12B	108.1
C10A—C9—H9B	109.5	C11B—C12—H12C	109.1
H9A—C9—H9B	108.1	C7—C12—H12C	109.8
C8—C9—H9C	110.3	C11A—C12—H12C	82.8
C10B—C9—H9C	109.0	H12B—C12—H12C	130.7
C10A—C9—H9C	85.6	C11B—C12—H12D	109.5
H9B—C9—H9C	128.2	C7—C12—H12D	109.4
C8—C9—H9D	109.9	C11A—C12—H12D	131.9
C10B—C9—H9D	111.5	H12A—C12—H12D	81.1
C10A—C9—H9D	128.3	H12C—C12—H12D	108.1
H9A—C9—H9D	84.9
C6—C1—C2—C3	−0.4 (3)	C5—N1—C8—C7	−1.0 (2)
C1—C2—C3—C4	0.1 (3)	C5—N1—C8—C9	177.78 (18)
C2—C3—C4—C5	0.0 (3)	C7—C8—C9—C10B	14.1 (5)
C8—N1—C5—C4	−178.92 (19)	N1—C8—C9—C10B	−164.5 (5)
C8—N1—C5—C6	0.7 (2)	C7—C8—C9—C10A	−11.7 (4)
C3—C4—C5—N1	179.77 (19)	N1—C8—C9—C10A	169.7 (3)
C3—C4—C5—C6	0.2 (3)	C8—C9—C10A—C11A	40.6 (8)
C2—C1—C6—C5	0.6 (3)	C10B—C9—C10A—C11A	−46.8 (11)
C2—C1—C6—C7	−179.34 (19)	C9—C10A—C11A—C12	−59.6 (9)
N1—C5—C6—C1	179.87 (15)	C8—C9—C10B—C11B	−43.8 (11)
C4—C5—C6—C1	−0.4 (3)	C10A—C9—C10B—C11B	57.5 (12)
N1—C5—C6—C7	−0.20 (18)	C9—C10B—C11B—C12	61.8 (14)
C4—C5—C6—C7	179.48 (17)	C10B—C11B—C12—C7	−42.9 (10)
C1—C6—C7—C8	179.52 (19)	C10B—C11B—C12—C11A	51.4 (8)
C5—C6—C7—C8	−0.39 (18)	C8—C7—C12—C11B	14.2 (5)
C1—C6—C7—C12	1.6 (3)	C6—C7—C12—C11B	−168.1 (5)
C5—C6—C7—C12	−178.35 (17)	C8—C7—C12—C11A	−17.0 (4)
C6—C7—C8—N1	0.84 (19)	C6—C7—C12—C11A	160.7 (3)
C12—C7—C8—N1	178.98 (16)	C10A—C11A—C12—C11B	−51.7 (7)
C6—C7—C8—C9	−177.92 (18)	C10A—C11A—C12—C7	45.1 (7)
C12—C7—C8—C9	0.2 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···Cg2i	0.86	2.62	3.327 (1)	140
C4—H4···Cg1i	0.93	2.86	3.645 (1)	143
C12—H12B···Cg2ii	0.97	2.83	3.577 (2)	135
C12—H12D···Cg2ii	0.96	2.72	3.577 (2)	149

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯Cg2i	0.86	2.62	3.327 (1)	140
C4—H4⋯Cg1i	0.93	2.86	3.645 (1)	143
C12—H12B⋯Cg2ii	0.97	2.83	3.577 (2)	135
C12—H12D⋯Cg2ii	0.96	2.72	3.577 (2)	149

Symmetry codes: (i) ; (ii) .Cg1 and Cg2 are the centroids of the N1/C5–C8 and C1–C6 rings, respectively.