2-Methyl-1-phenyl-1H-indole-3-carbo-nitrile.

In the title compound, C(16)H(12)N(2), the dihedral angle between the indole ring system and the pendant phenyl ring is 64.92 (5)°. The crystal packing features aromatic π-π stacking [centroid-centroid separation = 3.9504 (9) Å] and C-H⋯π inter-actions.

Related literature

For the synthesis of the title compound, see: Du et al. (2006 ▶). For its precursor, see: Jin et al. (2009 ▶). For related structures, see: Yang et al. (2011 ▶); Yan & Qi (2011a ▶,b ▶).

Experimental

Crystal data

C16H12N2

M = 232.28

Triclinic,

a = 6.3610 (5) Å

b = 9.497 (1) Å

c = 11.0210 (12) Å

α = 65.97 (2)°

β = 80.52 (2)°

γ = 88.13 (2)°

V = 599.34 (14) Å3

Z = 2

Mo Kα radiation

μ = 0.08 mm−1

T = 113 K

0.26 × 0.24 × 0.06 mm

Data collection

Rigaku Saturn724 CCD diffractometer

Absorption correction: multi-scan (CrystalClear-SM Expert; Rigaku, 2009 ▶) T min = 0.980, T max = 0.995

11425 measured reflections

3494 independent reflections

2309 reflections with I > 2σ(I)

R int = 0.040

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.120

S = 0.98

3494 reflections

164 parameters

H-atom parameters constrained

Δρmax = 0.45 e Å−3

Δρmin = −0.29 e Å−3

Data collection: CrystalClear-SM Expert (Rigaku 2009 ▶); cell refinement: CrystalClear-SM Expert; data reduction: CrystalClear-SM Expert; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: CrystalStructure (Rigaku, 2009 ▶); software used to prepare material for publication: CrystalStructure.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811039250/hb6411sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811039250/hb6411Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811039250/hb6411Isup3.cml

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

C16H12N2	Z = 2
Mr = 232.28	F(000) = 244
Triclinic, P1	Dx = 1.287 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71075 Å
a = 6.3610 (5) Å	Cell parameters from 2709 reflections
b = 9.497 (1) Å	θ = 2.1–33.5°
c = 11.0210 (12) Å	µ = 0.08 mm−1
α = 65.97 (2)°	T = 113 K
β = 80.52 (2)°	Prism, colorless
γ = 88.13 (2)°	0.26 × 0.24 × 0.06 mm
V = 599.34 (14) Å3

Rigaku Saturn724 CCD diffractometer	3494 independent reflections
Radiation source: rotating anode	2309 reflections with I > 2σ(I)
multilayer	Rint = 0.040
Detector resolution: 14.222 pixels mm-1	θmax = 30.0°, θmin = 2.1°
ω scans	h = −8→8
Absorption correction: multi-scan (CrystalClear-SM Expert; Rigaku, 2009)	k = −13→13
Tmin = 0.980, Tmax = 0.995	l = −15→15
11425 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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.120	H-atom parameters constrained
S = 0.98	w = 1/[σ2(Fo2) + (0.0674P)2] where P = (Fo2 + 2Fc2)/3
3494 reflections	(Δ/σ)max = 0.002
164 parameters	Δρmax = 0.45 e Å−3
0 restraints	Δρmin = −0.29 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.

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	0.44315 (14)	0.77239 (10)	0.77878 (9)	0.0185 (2)
N2	0.81470 (18)	0.84332 (13)	0.34779 (11)	0.0345 (3)
C1	0.60803 (17)	0.82767 (13)	0.67167 (11)	0.0194 (2)
C2	0.56979 (18)	0.77831 (13)	0.57514 (11)	0.0209 (2)
C3	0.37200 (18)	0.68851 (13)	0.62387 (11)	0.0202 (2)
C4	0.29646 (17)	0.68823 (12)	0.75088 (11)	0.0187 (2)
C5	0.10695 (18)	0.61245 (13)	0.82939 (11)	0.0216 (2)
H5	0.0582	0.6142	0.9150	0.026*
C6	−0.00823 (18)	0.53441 (14)	0.77872 (12)	0.0249 (3)
H6	−0.1391	0.4820	0.8299	0.030*
C7	0.06551 (19)	0.53158 (14)	0.65265 (12)	0.0275 (3)
H7	−0.0158	0.4763	0.6202	0.033*
C8	0.2539 (2)	0.60756 (14)	0.57463 (12)	0.0257 (3)
H8	0.3024	0.6049	0.4893	0.031*
C9	0.78658 (18)	0.92844 (14)	0.66577 (12)	0.0246 (3)
H9A	0.9227	0.8851	0.6449	0.030*
H9B	0.7777	0.9348	0.7530	0.030*
H9C	0.7772	1.0319	0.5955	0.030*
C10	0.70487 (19)	0.81451 (14)	0.44957 (12)	0.0240 (3)
C11	0.42676 (17)	0.78451 (12)	0.90546 (11)	0.0192 (2)
C12	0.57306 (19)	0.71355 (14)	0.98980 (12)	0.0248 (3)
H12	0.6857	0.6588	0.9629	0.030*
C13	0.5548 (2)	0.72252 (14)	1.11344 (12)	0.0285 (3)
H13	0.6578	0.6773	1.1701	0.034*
C14	0.3862 (2)	0.79746 (14)	1.15407 (12)	0.0293 (3)
H14	0.3723	0.8027	1.2393	0.035*
C15	0.2379 (2)	0.86476 (15)	1.07108 (12)	0.0313 (3)
H15	0.1207	0.9144	1.1002	0.038*
C16	0.25896 (19)	0.86032 (14)	0.94531 (12)	0.0261 (3)
H16	0.1589	0.9090	0.8873	0.031*

	U11	U22	U33	U12	U13	U23
N1	0.0180 (5)	0.0208 (5)	0.0170 (5)	0.0005 (4)	−0.0012 (3)	−0.0085 (4)
N2	0.0369 (6)	0.0412 (7)	0.0228 (5)	−0.0072 (5)	0.0039 (4)	−0.0131 (5)
C1	0.0185 (5)	0.0204 (5)	0.0174 (5)	0.0010 (4)	−0.0014 (4)	−0.0064 (4)
C2	0.0217 (6)	0.0224 (5)	0.0162 (5)	−0.0005 (4)	−0.0008 (4)	−0.0063 (4)
C3	0.0207 (6)	0.0209 (5)	0.0168 (5)	0.0004 (4)	−0.0029 (4)	−0.0054 (4)
C4	0.0187 (5)	0.0191 (5)	0.0177 (5)	0.0016 (4)	−0.0038 (4)	−0.0066 (4)
C5	0.0198 (6)	0.0236 (6)	0.0190 (5)	0.0003 (4)	−0.0006 (4)	−0.0071 (4)
C6	0.0198 (6)	0.0270 (6)	0.0247 (6)	−0.0036 (5)	−0.0030 (5)	−0.0072 (5)
C7	0.0279 (6)	0.0304 (6)	0.0253 (6)	−0.0051 (5)	−0.0080 (5)	−0.0108 (5)
C8	0.0306 (7)	0.0289 (6)	0.0178 (6)	−0.0019 (5)	−0.0056 (5)	−0.0089 (5)
C9	0.0235 (6)	0.0259 (6)	0.0228 (6)	−0.0043 (5)	0.0005 (4)	−0.0096 (5)
C10	0.0253 (6)	0.0261 (6)	0.0191 (6)	−0.0029 (5)	−0.0018 (4)	−0.0082 (5)
C11	0.0211 (5)	0.0191 (5)	0.0167 (5)	−0.0013 (4)	−0.0007 (4)	−0.0072 (4)
C12	0.0223 (6)	0.0291 (6)	0.0244 (6)	0.0048 (5)	−0.0032 (5)	−0.0127 (5)
C13	0.0323 (7)	0.0331 (7)	0.0220 (6)	0.0037 (5)	−0.0097 (5)	−0.0116 (5)
C14	0.0408 (8)	0.0278 (6)	0.0209 (6)	0.0001 (5)	−0.0030 (5)	−0.0121 (5)
C15	0.0363 (7)	0.0327 (7)	0.0267 (7)	0.0101 (6)	−0.0012 (5)	−0.0162 (5)
C16	0.0274 (6)	0.0287 (6)	0.0240 (6)	0.0086 (5)	−0.0059 (5)	−0.0123 (5)

N1—C1	1.3757 (14)	C7—H7	0.9500
N1—C4	1.3955 (14)	C8—H8	0.9500
N1—C11	1.4337 (13)	C9—H9A	0.9800
N2—C10	1.1514 (15)	C9—H9B	0.9800
C1—C2	1.3819 (16)	C9—H9C	0.9800
C1—C9	1.4853 (16)	C11—C16	1.3797 (16)
C2—C10	1.4183 (16)	C11—C12	1.3849 (16)
C2—C3	1.4398 (17)	C12—C13	1.3854 (16)
C3—C8	1.4006 (16)	C12—H12	0.9500
C3—C4	1.4020 (15)	C13—C14	1.3815 (17)
C4—C5	1.3877 (16)	C13—H13	0.9500
C5—C6	1.3804 (16)	C14—C15	1.3797 (17)
C5—H5	0.9500	C14—H14	0.9500
C6—C7	1.4021 (17)	C15—C16	1.3881 (16)
C6—H6	0.9500	C15—H15	0.9500
C7—C8	1.3813 (17)	C16—H16	0.9500
C1—N1—C4	109.22 (9)	C3—C8—H8	120.7
C1—N1—C11	127.12 (9)	C1—C9—H9A	109.5
C4—N1—C11	123.45 (9)	C1—C9—H9B	109.5
N1—C1—C2	108.27 (10)	H9A—C9—H9B	109.5
N1—C1—C9	123.13 (10)	C1—C9—H9C	109.5
C2—C1—C9	128.56 (10)	H9A—C9—H9C	109.5
C1—C2—C10	124.37 (11)	H9B—C9—H9C	109.5
C1—C2—C3	108.35 (10)	N2—C10—C2	179.74 (14)
C10—C2—C3	127.28 (11)	C16—C11—C12	120.47 (10)
C8—C3—C4	119.01 (11)	C16—C11—N1	119.62 (10)
C8—C3—C2	135.08 (11)	C12—C11—N1	119.82 (10)
C4—C3—C2	105.90 (10)	C11—C12—C13	119.86 (11)
C5—C4—N1	129.20 (10)	C11—C12—H12	120.1
C5—C4—C3	122.53 (10)	C13—C12—H12	120.1
N1—C4—C3	108.27 (10)	C14—C13—C12	119.80 (11)
C6—C5—C4	117.64 (11)	C14—C13—H13	120.1
C6—C5—H5	121.2	C12—C13—H13	120.1
C4—C5—H5	121.2	C15—C14—C13	120.11 (11)
C5—C6—C7	120.81 (11)	C15—C14—H14	119.9
C5—C6—H6	119.6	C13—C14—H14	119.9
C7—C6—H6	119.6	C14—C15—C16	120.38 (11)
C8—C7—C6	121.36 (11)	C14—C15—H15	119.8
C8—C7—H7	119.3	C16—C15—H15	119.8
C6—C7—H7	119.3	C11—C16—C15	119.33 (11)
C7—C8—C3	118.63 (11)	C11—C16—H16	120.3
C7—C8—H8	120.7	C15—C16—H16	120.3
C4—N1—C1—C2	−0.61 (12)	C3—C4—C5—C6	0.38 (17)
C11—N1—C1—C2	174.22 (9)	C4—C5—C6—C7	0.39 (17)
C4—N1—C1—C9	177.02 (10)	C5—C6—C7—C8	−0.60 (18)
C11—N1—C1—C9	−8.15 (16)	C6—C7—C8—C3	0.03 (18)
N1—C1—C2—C10	179.25 (10)	C4—C3—C8—C7	0.71 (17)
C9—C1—C2—C10	1.79 (19)	C2—C3—C8—C7	179.55 (12)
N1—C1—C2—C3	0.15 (12)	C1—C2—C10—N2	113 (37)
C9—C1—C2—C3	−177.31 (11)	C3—C2—C10—N2	−68 (37)
C1—C2—C3—C8	−178.58 (13)	C1—N1—C11—C16	119.92 (13)
C10—C2—C3—C8	2.4 (2)	C4—N1—C11—C16	−65.94 (14)
C1—C2—C3—C4	0.36 (12)	C1—N1—C11—C12	−63.31 (15)
C10—C2—C3—C4	−178.71 (11)	C4—N1—C11—C12	110.84 (13)
C1—N1—C4—C5	−179.85 (11)	C16—C11—C12—C13	−1.93 (18)
C11—N1—C4—C5	5.09 (17)	N1—C11—C12—C13	−178.67 (10)
C1—N1—C4—C3	0.85 (12)	C11—C12—C13—C14	2.34 (19)
C11—N1—C4—C3	−174.22 (9)	C12—C13—C14—C15	−0.77 (19)
C8—C3—C4—C5	−0.94 (16)	C13—C14—C15—C16	−1.2 (2)
C2—C3—C4—C5	179.91 (10)	C12—C11—C16—C15	−0.06 (18)
C8—C3—C4—N1	178.42 (10)	N1—C11—C16—C15	176.69 (10)
C2—C3—C4—N1	−0.73 (12)	C14—C15—C16—C11	1.64 (19)
N1—C4—C5—C6	−178.84 (10)

Cg2 and Cg3 are the centroids of the C3–C8 and C11–C16 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···Cg3i	0.95	2.85	3.719 (1)	152
C9—H9A···Cg2ii	0.98	2.94	3.799 (2)	147
C13—H13···Cg2iii	0.95	2.77	3.537 (2)	139

Table 1

Hydrogen-bond geometry (Å, °)

Cg2 and Cg3 are the centroids of the C3–C8 and C11–C16 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6⋯Cg3i	0.95	2.85	3.719 (1)	152
C9—H9A⋯Cg2ii	0.98	2.94	3.799 (2)	147
C13—H13⋯Cg2iii	0.95	2.77	3.537 (2)	139

Symmetry codes: (i) ; (ii) ; (iii) .