2-(1,2,3,4-Tetra-hydro-9H-carbazol-1-yl-idene)propane-dinitrile.

In the title compound, C(15)H(11)N(3), the cyclo-hexene ring adopts a sofa conformation. An intra-molecular N-H⋯N hydrogen bond generates an S(7) ring motif. In the crystal, mol-ecules are linked by inter-molecular N-H⋯N, C-H⋯N and C-H⋯π inter-actions into a three-dimensional network.

Related literature

For the biological activity of carbazole derivatives, see: Shufen et al. (1995 ▶); Magnus et al. (1992 ▶); Abraham (1975 ▶); Saxton (1983 ▶); Phillipson & Zenk (1980 ▶); Bergman & Pelcman (1990 ▶); Kirtikar & Basu (1933 ▶); Chakraborty et al. (1973 ▶). For puckering parameters, see: Cremer & Pople (1975 ▶). For asymmetry parameters, see: Nardelli (1983 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C15H11N3

M = 233.27

Triclinic,

a = 7.7631 (10) Å

b = 8.0003 (10) Å

c = 9.8933 (13) Å

α = 87.461 (8)°

β = 82.392 (8)°

γ = 75.038 (7)°

V = 588.35 (13) Å3

Z = 2

Mo Kα radiation

μ = 0.08 mm−1

T = 293 K

0.20 × 0.18 × 0.17 mm

Data collection

Bruker SMART APEXII area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T min = 0.984, T max = 0.986

10589 measured reflections

2924 independent reflections

2339 reflections with I > 2σ(I)

R int = 0.039

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.130

S = 1.06

2924 reflections

168 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.23 e Å−3

Δρmin = −0.15 e Å−3

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT (Bruker, 2008 ▶); 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, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810042649/bt5359sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810042649/bt5359Isup2.hkl

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

C15H11N3	Z = 2
Mr = 233.27	F(000) = 244
Triclinic, P1	Dx = 1.317 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.7631 (10) Å	Cell parameters from 1654 reflections
b = 8.0003 (10) Å	θ = 2.1–28.4°
c = 9.8933 (13) Å	µ = 0.08 mm−1
α = 87.461 (8)°	T = 293 K
β = 82.392 (8)°	Block, colorless
γ = 75.038 (7)°	0.20 × 0.18 × 0.17 mm
V = 588.35 (13) Å3

Bruker SMART APEXII area-detector diffractometer	2924 independent reflections
Radiation source: fine-focus sealed tube	2339 reflections with I > 2σ(I)
graphite	Rint = 0.039
ω and φ scans	θmax = 28.4°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −10→10
Tmin = 0.984, Tmax = 0.986	k = −10→10
10589 measured reflections	l = −12→13

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)] = 0.041	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.130	w = 1/[σ2(Fo2) + (0.0748P)2 + 0.0374P] where P = (Fo2 + 2Fc2)/3
S = 1.06	(Δ/σ)max = 0.003
2924 reflections	Δρmax = 0.23 e Å−3
168 parameters	Δρmin = −0.15 e Å−3
2 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.038 (8)

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	0.18203 (13)	0.14402 (13)	0.01388 (9)	0.0404 (2)
H1	0.118 (2)	0.252 (2)	0.0038 (17)	0.068 (4)*
C2	0.25866 (13)	0.06198 (14)	0.12645 (10)	0.0375 (2)
C3	0.26818 (13)	0.13570 (14)	0.25321 (10)	0.0380 (3)
C4	0.36565 (17)	0.01146 (17)	0.35406 (13)	0.0491 (3)
H4A	0.3179	0.0527	0.4456	0.059*
H4B	0.4918	0.0112	0.3398	0.059*
C5	0.35020 (18)	−0.17242 (16)	0.34360 (13)	0.0532 (3)
H5A	0.2257	−0.1756	0.3670	0.064*
H5B	0.4204	−0.2461	0.4078	0.064*
C6	0.41700 (17)	−0.23982 (16)	0.20031 (13)	0.0518 (3)
H6A	0.5464	−0.2582	0.1830	0.062*
H6B	0.3889	−0.3498	0.1910	0.062*
C7	0.32980 (14)	−0.11254 (14)	0.09931 (11)	0.0412 (3)
C8	0.29475 (14)	−0.13856 (15)	−0.03433 (12)	0.0430 (3)
C9	0.32862 (18)	−0.28496 (18)	−0.11570 (14)	0.0559 (3)
H9	0.3900	−0.3926	−0.0849	0.067*
C10	0.26989 (19)	−0.2670 (2)	−0.24143 (15)	0.0621 (4)
H10	0.2916	−0.3636	−0.2963	0.075*
C11	0.17753 (18)	−0.1052 (2)	−0.28854 (13)	0.0561 (3)
H11	0.1390	−0.0972	−0.3743	0.067*
C12	0.14204 (16)	0.04168 (17)	−0.21264 (11)	0.0486 (3)
H12	0.0815	0.1487	−0.2451	0.058*
C13	0.20122 (14)	0.02303 (15)	−0.08386 (11)	0.0407 (3)
C14	0.20193 (15)	0.30577 (15)	0.28668 (11)	0.0436 (3)
C15	0.11508 (19)	0.43809 (15)	0.19901 (13)	0.0519 (3)
N16	0.0464 (2)	0.54705 (16)	0.13082 (13)	0.0753 (4)
C17	0.22133 (19)	0.36577 (18)	0.41741 (14)	0.0575 (3)
N18	0.2367 (2)	0.4156 (2)	0.51944 (15)	0.0918 (5)

	U11	U22	U33	U12	U13	U23
N1	0.0490 (5)	0.0377 (5)	0.0343 (5)	−0.0091 (4)	−0.0075 (4)	−0.0041 (4)
C2	0.0391 (5)	0.0380 (5)	0.0360 (5)	−0.0103 (4)	−0.0051 (4)	−0.0024 (4)
C3	0.0375 (5)	0.0424 (6)	0.0356 (5)	−0.0120 (4)	−0.0056 (4)	−0.0026 (4)
C4	0.0505 (6)	0.0526 (7)	0.0441 (6)	−0.0081 (5)	−0.0158 (5)	0.0000 (5)
C5	0.0597 (7)	0.0476 (7)	0.0496 (7)	−0.0054 (5)	−0.0160 (5)	0.0062 (5)
C6	0.0517 (6)	0.0408 (6)	0.0591 (7)	−0.0023 (5)	−0.0114 (5)	−0.0020 (5)
C7	0.0392 (5)	0.0395 (6)	0.0435 (6)	−0.0073 (4)	−0.0035 (4)	−0.0055 (4)
C8	0.0418 (5)	0.0427 (6)	0.0433 (6)	−0.0102 (4)	0.0009 (4)	−0.0103 (5)
C9	0.0591 (7)	0.0477 (7)	0.0585 (8)	−0.0100 (5)	0.0009 (6)	−0.0191 (6)
C10	0.0647 (8)	0.0658 (9)	0.0577 (8)	−0.0225 (7)	0.0074 (6)	−0.0300 (7)
C11	0.0576 (7)	0.0769 (9)	0.0397 (6)	−0.0278 (7)	0.0000 (5)	−0.0173 (6)
C12	0.0521 (6)	0.0592 (7)	0.0371 (6)	−0.0183 (5)	−0.0043 (5)	−0.0075 (5)
C13	0.0418 (5)	0.0458 (6)	0.0357 (5)	−0.0140 (4)	−0.0010 (4)	−0.0075 (4)
C14	0.0511 (6)	0.0433 (6)	0.0391 (5)	−0.0133 (5)	−0.0107 (4)	−0.0061 (4)
C15	0.0725 (8)	0.0386 (6)	0.0466 (6)	−0.0132 (5)	−0.0150 (5)	−0.0068 (5)
N16	0.1197 (11)	0.0434 (6)	0.0624 (8)	−0.0100 (7)	−0.0318 (7)	0.0008 (6)
C17	0.0693 (8)	0.0528 (7)	0.0502 (7)	−0.0071 (6)	−0.0194 (6)	−0.0137 (6)
N18	0.1192 (12)	0.0874 (10)	0.0674 (9)	−0.0048 (9)	−0.0392 (8)	−0.0328 (8)

N1—C13	1.3655 (14)	C7—C8	1.4193 (16)
N1—C2	1.3906 (14)	C8—C9	1.3991 (16)
N1—H1	0.885 (17)	C8—C13	1.4114 (17)
C2—C7	1.3865 (15)	C9—C10	1.370 (2)
C2—C3	1.4278 (15)	C9—H9	0.9300
C3—C14	1.3634 (16)	C10—C11	1.401 (2)
C3—C4	1.5098 (16)	C10—H10	0.9300
C4—C5	1.5156 (19)	C11—C12	1.3698 (18)
C4—H4A	0.9700	C11—H11	0.9300
C4—H4B	0.9700	C12—C13	1.3997 (16)
C5—C6	1.5159 (18)	C12—H12	0.9300
C5—H5A	0.9700	C14—C15	1.4257 (17)
C5—H5B	0.9700	C14—C17	1.4386 (16)
C6—C7	1.4921 (16)	C15—N16	1.1413 (17)
C6—H6A	0.9700	C17—N18	1.1334 (17)
C6—H6B	0.9700
C13—N1—C2	108.44 (9)	C2—C7—C8	106.56 (10)
C13—N1—H1	121.1 (11)	C2—C7—C6	123.35 (10)
C2—N1—H1	130.1 (11)	C8—C7—C6	130.04 (10)
C7—C2—N1	109.30 (9)	C9—C8—C13	119.21 (12)
C7—C2—C3	122.29 (10)	C9—C8—C7	133.37 (12)
N1—C2—C3	128.42 (10)	C13—C8—C7	107.37 (10)
C14—C3—C2	125.47 (10)	C10—C9—C8	118.88 (13)
C14—C3—C4	119.15 (10)	C10—C9—H9	120.6
C2—C3—C4	115.36 (10)	C8—C9—H9	120.6
C3—C4—C5	113.84 (10)	C9—C10—C11	120.89 (12)
C3—C4—H4A	108.8	C9—C10—H10	119.6
C5—C4—H4A	108.8	C11—C10—H10	119.6
C3—C4—H4B	108.8	C12—C11—C10	122.23 (12)
C5—C4—H4B	108.8	C12—C11—H11	118.9
H4A—C4—H4B	107.7	C10—C11—H11	118.9
C4—C5—C6	110.58 (11)	C11—C12—C13	116.83 (13)
C4—C5—H5A	109.5	C11—C12—H12	121.6
C6—C5—H5A	109.5	C13—C12—H12	121.6
C4—C5—H5B	109.5	N1—C13—C12	129.73 (11)
C6—C5—H5B	109.5	N1—C13—C8	108.31 (10)
H5A—C5—H5B	108.1	C12—C13—C8	121.95 (11)
C7—C6—C5	109.78 (10)	C3—C14—C15	125.01 (10)
C7—C6—H6A	109.7	C3—C14—C17	120.54 (11)
C5—C6—H6A	109.7	C15—C14—C17	114.43 (11)
C7—C6—H6B	109.7	N16—C15—C14	178.28 (13)
C5—C6—H6B	109.7	N18—C17—C14	178.87 (17)
H6A—C6—H6B	108.2
C13—N1—C2—C7	0.92 (12)	C7—C8—C9—C10	177.34 (12)
C13—N1—C2—C3	−179.03 (10)	C8—C9—C10—C11	0.1 (2)
C7—C2—C3—C14	179.75 (10)	C9—C10—C11—C12	0.2 (2)
N1—C2—C3—C14	−0.31 (19)	C10—C11—C12—C13	−0.53 (18)
C7—C2—C3—C4	1.66 (15)	C2—N1—C13—C12	178.09 (11)
N1—C2—C3—C4	−178.40 (10)	C2—N1—C13—C8	−1.16 (12)
C14—C3—C4—C5	150.75 (11)	C11—C12—C13—N1	−178.53 (11)
C2—C3—C4—C5	−31.03 (14)	C11—C12—C13—C8	0.64 (17)
C3—C4—C5—C6	56.40 (14)	C9—C8—C13—N1	178.93 (10)
C4—C5—C6—C7	−50.35 (13)	C7—C8—C13—N1	0.97 (12)
N1—C2—C7—C8	−0.30 (12)	C9—C8—C13—C12	−0.40 (17)
C3—C2—C7—C8	179.65 (9)	C7—C8—C13—C12	−178.35 (10)
N1—C2—C7—C6	−177.95 (10)	C2—C3—C14—C15	−1.19 (19)
C3—C2—C7—C6	2.00 (17)	C4—C3—C14—C15	176.84 (11)
C5—C6—C7—C2	23.15 (15)	C2—C3—C14—C17	−179.26 (11)
C5—C6—C7—C8	−153.90 (12)	C4—C3—C14—C17	−1.23 (17)
C2—C7—C8—C9	−177.95 (12)	C3—C14—C15—N16	−161 (5)
C6—C7—C8—C9	−0.5 (2)	C17—C14—C15—N16	17 (5)
C2—C7—C8—C13	−0.40 (12)	C3—C14—C17—N18	149 (9)
C6—C7—C8—C13	177.03 (11)	C15—C14—C17—N18	−30 (9)
C13—C8—C9—C10	0.02 (18)

Cg3 is the centroid of the C8–C13 ring.

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···N16	0.885 (17)	2.623 (17)	3.3314 (16)	137.8 (13)
N1—H1···N16i	0.885 (17)	2.279 (17)	3.0656 (17)	148.1 (14)
C12—H12···N16i	0.93	2.62	3.3254 (19)	133
C4—H4B···Cg3ii	0.97	2.86	3.6950 (15)	145

Table 1

Hydrogen-bond geometry (Å, °)

Cg3 is the centroid of the C8–C13 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯N16	0.885 (17)	2.623 (17)	3.3314 (16)	137.8 (13)
N1—H1⋯N16i	0.885 (17)	2.279 (17)	3.0656 (17)	148.1 (14)
C12—H12⋯N16i	0.93	2.62	3.3254 (19)	133
C4—H4B⋯Cg3ii	0.97	2.86	3.6950 (15)	145

Symmetry codes: (i) ; (ii) .