9-p-Tolyl-9H-carbazole-3-carbonitrile.

In the title compound, C(20)H(14)N(2), the carbazole ring system is essentially planar (r.m.s. deviation = 0.187 Å) and is inclined at an angle of 54.33 (4) ° with respect to the benzene ring. The crystal packing is stabilized by weak C-H⋯N and C-H⋯π inter-actions.

Related literature

For the biological activity of carbazole derivatives, see: Ramsewak et al. (1999 ▶); Tachibana et al. (2001 ▶); Itoigawa et al. (2000 ▶). For related structures, see: Archana et al. (2010 ▶); Velmurugan et al. (2010 ▶); Yuan et al. (2010 ▶).

Experimental

Crystal data

C20H14N2

M = 282.33

Triclinic,

a = 8.6031 (3) Å

b = 8.8247 (3) Å

c = 10.4609 (4) Å

α = 80.514 (2)°

β = 87.499 (2)°

γ = 72.114 (2)°

V = 745.45 (5) Å3

Z = 2

Mo Kα radiation

μ = 0.08 mm−1

T = 295 K

0.22 × 0.19 × 0.17 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.984, T max = 0.987

13631 measured reflections

3724 independent reflections

2695 reflections with I > 2σ(I)

R int = 0.029

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.123

S = 1.04

3724 reflections

200 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.16 e Å−3

Δρmin = −0.21 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: PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811039286/pv2449sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811039286/pv2449Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811039286/pv2449Isup3.cml

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

C20H14N2	Z = 2
Mr = 282.33	F(000) = 296
Triclinic, P1	Dx = 1.258 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.6031 (3) Å	Cell parameters from 3724 reflections
b = 8.8247 (3) Å	θ = 2.0–28.4°
c = 10.4609 (4) Å	µ = 0.08 mm−1
α = 80.514 (2)°	T = 295 K
β = 87.499 (2)°	Block, colourless
γ = 72.114 (2)°	0.22 × 0.19 × 0.17 mm
V = 745.45 (5) Å3

Bruker Kappa APEXII CCD diffractometer	3724 independent reflections
Radiation source: fine-focus sealed tube	2695 reflections with I > 2σ(I)
graphite	Rint = 0.029
Detector resolution: 0 pixels mm-1	θmax = 28.4°, θmin = 2.0°
ω and φ scans	h = −11→9
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −11→11
Tmin = 0.984, Tmax = 0.987	l = −13→13
13631 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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.123	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0561P)2 + 0.1087P] where P = (Fo2 + 2Fc2)/3
3724 reflections	(Δ/σ)max = 0.002
200 parameters	Δρmax = 0.16 e Å−3
1 restraint	Δρmin = −0.21 e Å−3

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.

	x	y	z	Uiso*/Ueq
C1	1.15482 (15)	0.39757 (15)	0.76616 (11)	0.0428 (3)
C2	1.28283 (17)	0.27239 (16)	0.72999 (13)	0.0503 (3)
H2	1.2641	0.1969	0.6851	0.060*
C3	1.43894 (17)	0.26447 (17)	0.76330 (13)	0.0544 (3)
H3	1.5267	0.1814	0.7408	0.065*
C4	1.46875 (17)	0.37727 (17)	0.82957 (13)	0.0540 (3)
H4	1.5755	0.3684	0.8503	0.065*
C5	1.34207 (15)	0.50179 (16)	0.86478 (12)	0.0482 (3)
H5	1.3622	0.5774	0.9087	0.058*
C6	1.18294 (15)	0.51223 (14)	0.83321 (11)	0.0413 (3)
C7	1.02493 (14)	0.62392 (14)	0.85320 (11)	0.0408 (3)
C8	0.97472 (15)	0.75589 (15)	0.91712 (12)	0.0447 (3)
H8	1.0505	0.7899	0.9561	0.054*
C9	0.80848 (16)	0.83680 (15)	0.92188 (12)	0.0470 (3)
C10	0.69339 (16)	0.78683 (16)	0.86297 (13)	0.0513 (3)
H10	0.5829	0.8431	0.8670	0.062*
C11	0.74155 (16)	0.65580 (16)	0.79929 (13)	0.0497 (3)
H11	0.6653	0.6228	0.7599	0.060*
C12	0.90815 (15)	0.57363 (15)	0.79534 (11)	0.0428 (3)
C13	0.91238 (15)	0.35356 (16)	0.67085 (12)	0.0447 (3)
C14	0.81166 (17)	0.43835 (18)	0.56626 (12)	0.0531 (3)
H14	0.7938	0.5487	0.5431	0.064*
C15	0.73821 (18)	0.3594 (2)	0.49679 (13)	0.0588 (4)
H15	0.6688	0.4181	0.4282	0.071*
C16	0.76514 (18)	0.1943 (2)	0.52662 (14)	0.0582 (4)
C17	0.86723 (18)	0.11099 (18)	0.63019 (15)	0.0582 (4)
H17	0.8883	−0.0001	0.6512	0.070*
C18	0.93897 (17)	0.18914 (16)	0.70359 (13)	0.0517 (3)
H18	1.0047	0.1313	0.7745	0.062*
C19	0.6847 (3)	0.1091 (3)	0.4495 (2)	0.0915 (6)
H19A	0.5682	0.1520	0.4557	0.137*
H19B	0.7182	−0.0041	0.4832	0.137*
H19C	0.7163	0.1249	0.3603	0.137*
C20	0.75645 (17)	0.97199 (16)	0.99028 (14)	0.0537 (3)
N1	0.98705 (12)	0.43589 (13)	0.74328 (10)	0.0454 (3)
N2	0.72084 (16)	1.07784 (16)	1.04614 (14)	0.0700 (4)

	U11	U22	U33	U12	U13	U23
C1	0.0421 (6)	0.0455 (7)	0.0405 (6)	−0.0140 (5)	0.0003 (5)	−0.0053 (5)
C2	0.0519 (8)	0.0486 (7)	0.0508 (7)	−0.0142 (6)	0.0048 (6)	−0.0122 (6)
C3	0.0440 (7)	0.0523 (8)	0.0608 (8)	−0.0070 (6)	0.0063 (6)	−0.0083 (6)
C4	0.0411 (7)	0.0592 (8)	0.0590 (8)	−0.0140 (6)	−0.0018 (6)	−0.0039 (6)
C5	0.0438 (7)	0.0531 (7)	0.0482 (7)	−0.0157 (6)	−0.0035 (5)	−0.0061 (6)
C6	0.0420 (6)	0.0432 (6)	0.0386 (6)	−0.0137 (5)	0.0001 (5)	−0.0049 (5)
C7	0.0397 (6)	0.0426 (6)	0.0398 (6)	−0.0132 (5)	−0.0003 (5)	−0.0044 (5)
C8	0.0462 (7)	0.0432 (7)	0.0461 (6)	−0.0154 (5)	−0.0011 (5)	−0.0072 (5)
C9	0.0486 (7)	0.0412 (6)	0.0489 (7)	−0.0112 (5)	0.0020 (5)	−0.0060 (5)
C10	0.0409 (7)	0.0484 (7)	0.0616 (8)	−0.0097 (5)	0.0015 (6)	−0.0079 (6)
C11	0.0413 (7)	0.0525 (7)	0.0572 (7)	−0.0163 (6)	−0.0021 (6)	−0.0096 (6)
C12	0.0435 (7)	0.0425 (6)	0.0432 (6)	−0.0143 (5)	−0.0006 (5)	−0.0061 (5)
C13	0.0451 (7)	0.0519 (7)	0.0417 (6)	−0.0197 (6)	0.0029 (5)	−0.0120 (5)
C14	0.0586 (8)	0.0568 (8)	0.0467 (7)	−0.0234 (7)	−0.0034 (6)	−0.0040 (6)
C15	0.0592 (9)	0.0763 (10)	0.0456 (7)	−0.0267 (8)	−0.0038 (6)	−0.0098 (7)
C16	0.0549 (8)	0.0776 (10)	0.0552 (8)	−0.0319 (7)	0.0074 (6)	−0.0261 (7)
C17	0.0610 (9)	0.0531 (8)	0.0678 (9)	−0.0241 (7)	0.0063 (7)	−0.0184 (7)
C18	0.0529 (8)	0.0509 (7)	0.0524 (7)	−0.0168 (6)	−0.0016 (6)	−0.0085 (6)
C19	0.0912 (14)	0.1118 (16)	0.0975 (14)	−0.0513 (12)	−0.0035 (11)	−0.0491 (12)
C20	0.0492 (7)	0.0454 (7)	0.0637 (8)	−0.0097 (6)	0.0016 (6)	−0.0108 (6)
N1	0.0418 (6)	0.0472 (6)	0.0496 (6)	−0.0141 (5)	−0.0016 (4)	−0.0133 (5)
N2	0.0611 (8)	0.0583 (8)	0.0926 (10)	−0.0125 (6)	−0.0004 (7)	−0.0279 (7)

C1—C2	1.3894 (18)	C11—C12	1.3958 (18)
C1—N1	1.3995 (16)	C11—H11	0.9300
C1—C6	1.4048 (17)	C12—N1	1.3834 (16)
C2—C3	1.380 (2)	C13—C18	1.3835 (18)
C2—H2	0.9300	C13—C14	1.3865 (18)
C3—C4	1.392 (2)	C13—N1	1.4230 (16)
C3—H3	0.9300	C14—C15	1.3750 (19)
C4—C5	1.3761 (19)	C14—H14	0.9300
C4—H4	0.9300	C15—C16	1.386 (2)
C5—C6	1.3942 (17)	C15—H15	0.9300
C5—H5	0.9300	C16—C17	1.382 (2)
C6—C7	1.4434 (17)	C16—C19	1.505 (2)
C7—C8	1.3829 (17)	C17—C18	1.3869 (19)
C7—C12	1.4100 (17)	C17—H17	0.9300
C8—C9	1.3914 (18)	C18—H18	0.9300
C8—H8	0.9300	C19—H19A	0.9600
C9—C10	1.4021 (19)	C19—H19B	0.9600
C9—C20	1.4356 (18)	C19—H19C	0.9600
C10—C11	1.3740 (18)	C20—N2	1.1386 (17)
C10—H10	0.9300
C2—C1—N1	129.38 (12)	C12—C11—H11	120.9
C2—C1—C6	121.43 (12)	N1—C12—C11	129.52 (12)
N1—C1—C6	109.18 (11)	N1—C12—C7	109.05 (11)
C3—C2—C1	117.33 (13)	C11—C12—C7	121.40 (12)
C3—C2—H2	121.3	C18—C13—C14	119.34 (12)
C1—C2—H2	121.3	C18—C13—N1	120.73 (11)
C2—C3—C4	121.90 (13)	C14—C13—N1	119.93 (12)
C2—C3—H3	119.0	C15—C14—C13	120.07 (13)
C4—C3—H3	119.0	C15—C14—H14	120.0
C5—C4—C3	120.78 (13)	C13—C14—H14	120.0
C5—C4—H4	119.6	C14—C15—C16	121.56 (14)
C3—C4—H4	119.6	C14—C15—H15	119.2
C4—C5—C6	118.60 (13)	C16—C15—H15	119.2
C4—C5—H5	120.7	C17—C16—C15	117.77 (13)
C6—C5—H5	120.7	C17—C16—C19	121.14 (16)
C5—C6—C1	119.96 (12)	C15—C16—C19	121.09 (15)
C5—C6—C7	133.56 (12)	C16—C17—C18	121.52 (14)
C1—C6—C7	106.48 (11)	C16—C17—H17	119.2
C8—C7—C12	119.87 (11)	C18—C17—H17	119.2
C8—C7—C6	133.07 (11)	C13—C18—C17	119.71 (13)
C12—C7—C6	107.03 (10)	C13—C18—H18	120.1
C7—C8—C9	118.63 (11)	C17—C18—H18	120.1
C7—C8—H8	120.7	C16—C19—H19A	109.5
C9—C8—H8	120.7	C16—C19—H19B	109.5
C8—C9—C10	121.09 (12)	H19A—C19—H19B	109.5
C8—C9—C20	118.52 (12)	C16—C19—H19C	109.5
C10—C9—C20	120.38 (12)	H19A—C19—H19C	109.5
C11—C10—C9	120.90 (12)	H19B—C19—H19C	109.5
C11—C10—H10	119.6	N2—C20—C9	177.51 (16)
C9—C10—H10	119.6	C12—N1—C1	108.25 (10)
C10—C11—C12	118.11 (12)	C12—N1—C13	126.03 (10)
C10—C11—H11	120.9	C1—N1—C13	125.59 (10)
N1—C1—C2—C3	178.70 (12)	C8—C7—C12—C11	0.94 (18)
C6—C1—C2—C3	0.40 (19)	C6—C7—C12—C11	179.09 (11)
C1—C2—C3—C4	−0.5 (2)	C18—C13—C14—C15	0.5 (2)
C2—C3—C4—C5	0.1 (2)	N1—C13—C14—C15	−179.43 (12)
C3—C4—C5—C6	0.3 (2)	C13—C14—C15—C16	−1.6 (2)
C4—C5—C6—C1	−0.38 (18)	C14—C15—C16—C17	0.8 (2)
C4—C5—C6—C7	−179.43 (12)	C14—C15—C16—C19	−179.72 (14)
C2—C1—C6—C5	0.02 (18)	C15—C16—C17—C18	0.9 (2)
N1—C1—C6—C5	−178.58 (11)	C19—C16—C17—C18	−178.53 (14)
C2—C1—C6—C7	179.31 (11)	C14—C13—C18—C17	1.2 (2)
N1—C1—C6—C7	0.70 (13)	N1—C13—C18—C17	−178.86 (12)
C5—C6—C7—C8	−4.1 (2)	C16—C17—C18—C13	−1.9 (2)
C1—C6—C7—C8	176.79 (13)	C8—C9—C20—N2	−8(4)
C5—C6—C7—C12	178.13 (13)	C10—C9—C20—N2	171 (4)
C1—C6—C7—C12	−1.01 (13)	C11—C12—N1—C1	−178.47 (12)
C12—C7—C8—C9	−0.38 (17)	C7—C12—N1—C1	−0.55 (13)
C6—C7—C8—C9	−177.97 (12)	C11—C12—N1—C13	5.6 (2)
C7—C8—C9—C10	−0.23 (19)	C7—C12—N1—C13	−176.45 (11)
C7—C8—C9—C20	178.90 (11)	C2—C1—N1—C12	−178.57 (12)
C8—C9—C10—C11	0.3 (2)	C6—C1—N1—C12	−0.11 (13)
C20—C9—C10—C11	−178.79 (12)	C2—C1—N1—C13	−2.6 (2)
C9—C10—C11—C12	0.22 (19)	C6—C1—N1—C13	175.81 (11)
C10—C11—C12—N1	176.86 (12)	C18—C13—N1—C12	−128.91 (14)
C10—C11—C12—C7	−0.84 (19)	C14—C13—N1—C12	51.05 (17)
C8—C7—C12—N1	−177.18 (11)	C18—C13—N1—C1	55.88 (17)
C6—C7—C12—N1	0.97 (13)	C14—C13—N1—C1	−124.16 (14)

Cg2 is the centroid of the C1–C6 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8···N2i	0.93	2.57	3.434 (2)	154
C15—H15···Cg2ii	0.93	2.71	3.453 (1)	137

Table 1

Hydrogen-bond geometry (Å, °)

Cg2 is the centroid of the C1–C6 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C8—H8⋯N2i	0.93	2.57	3.434 (2)	154
C15—H15⋯Cg2ii	0.93	2.71	3.453 (1)	137

Symmetry codes: (i) ; (ii) .