6-Meth-oxy-2-methyl-1-phenyl-1H-indole-3-carbonitrile.

In the title compound, C(17)H(14)N(2)O, the dihedral angle between the indole ring system and the phenyl ring is 64.48 (7)°. The crystal packing features weak 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

C17H14N2O

M = 262.30

Triclinic,

a = 6.3699 (7) Å

b = 10.6084 (10) Å

c = 10.8139 (11) Å

α = 70.059 (10)°

β = 79.455 (13)°

γ = 78.869 (12)°

V = 668.55 (12) Å3

Z = 2

Mo Kα radiation

μ = 0.08 mm−1

T = 113 K

0.24 × 0.20 × 0.20 mm

Data collection

Rigaku Saturn724 CCD diffractometer

Absorption correction: multi-scan (CrystalClear-SM Expert; Rigaku, 2009 ▶) T min = 0.981, T max = 0.984

7078 measured reflections

3157 independent reflections

1404 reflections with I > 2σ(I)

R int = 0.052

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.095

S = 0.89

3157 reflections

184 parameters

H-atom parameters constrained

Δρmax = 0.36 e Å−3

Δρmin = −0.25 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/S1600536811038724/bt5647sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811038724/bt5647Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811038724/bt5647Isup3.cml

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

C17H14N2O	Z = 2
Mr = 262.30	F(000) = 276
Triclinic, P1	Dx = 1.303 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.3699 (7) Å	Cell parameters from 2377 reflections
b = 10.6084 (10) Å	θ = 2.0–28.1°
c = 10.8139 (11) Å	µ = 0.08 mm−1
α = 70.059 (10)°	T = 113 K
β = 79.455 (13)°	Prism, colorless
γ = 78.869 (12)°	0.24 × 0.20 × 0.20 mm
V = 668.55 (12) Å3

Rigaku Saturn724 CCD diffractometer	3157 independent reflections
Radiation source: fine-focus sealed tube	1404 reflections with I > 2σ(I)
graphite	Rint = 0.052
Detector resolution: 14.22 pixels mm-1	θmax = 28.0°, θmin = 2.0°
ω and φ scans	h = −8→8
Absorption correction: multi-scan (CrystalClear; Rigaku, 2009)	k = −13→13
Tmin = 0.981, Tmax = 0.984	l = −14→14
7078 measured 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)] = 0.041	H-atom parameters constrained
wR(F2) = 0.095	w = 1/[σ2(Fo2) + (0.0296P)2] where P = (Fo2 + 2Fc2)/3
S = 0.89	(Δ/σ)max < 0.001
3157 reflections	Δρmax = 0.36 e Å−3
184 parameters	Δρmin = −0.25 e Å−3
0 restraints	Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.048 (4)

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
O1	1.04602 (18)	0.50144 (11)	0.16822 (10)	0.0270 (3)
N1	0.4880 (2)	0.22413 (13)	0.23013 (11)	0.0196 (3)
N2	0.1580 (2)	0.13570 (16)	0.67436 (13)	0.0360 (4)
C1	0.6199 (3)	0.29364 (16)	0.26611 (14)	0.0191 (4)
C2	0.7805 (3)	0.36887 (16)	0.18802 (15)	0.0211 (4)
H2	0.8173	0.3779	0.0965	0.025*
C3	0.8845 (3)	0.42998 (17)	0.24916 (15)	0.0226 (4)
C4	0.8278 (3)	0.41970 (18)	0.38350 (15)	0.0260 (4)
H4	0.9008	0.4634	0.4228	0.031*
C5	0.6652 (3)	0.34576 (17)	0.45878 (15)	0.0257 (4)
H5	0.6261	0.3392	0.5496	0.031*
C6	0.5590 (3)	0.28104 (17)	0.40116 (14)	0.0203 (4)
C7	0.3836 (3)	0.20116 (17)	0.44466 (14)	0.0220 (4)
C8	0.3453 (3)	0.16698 (17)	0.33986 (15)	0.0217 (4)
C9	0.1853 (3)	0.08298 (18)	0.33621 (15)	0.0264 (4)
H9A	0.2120	0.0657	0.2508	0.040*
H9B	0.0392	0.1314	0.3472	0.040*
H9C	0.1996	−0.0033	0.4082	0.040*
C10	1.1759 (3)	0.55522 (18)	0.22829 (15)	0.0303 (5)
H10A	1.0862	0.6254	0.2622	0.045*
H10B	1.2925	0.5947	0.1620	0.045*
H10C	1.2377	0.4823	0.3016	0.045*
C11	0.2601 (3)	0.16396 (18)	0.57217 (16)	0.0261 (4)
C12	0.5114 (3)	0.20522 (17)	0.10210 (14)	0.0194 (4)
C13	0.3439 (3)	0.25740 (17)	0.02478 (15)	0.0238 (4)
H13	0.2171	0.3088	0.0539	0.029*
C14	0.3643 (3)	0.23346 (17)	−0.09557 (15)	0.0266 (4)
H14	0.2488	0.2655	−0.1480	0.032*
C15	0.5530 (3)	0.16287 (17)	−0.13911 (15)	0.0251 (4)
H15	0.5666	0.1472	−0.2218	0.030*
C16	0.7218 (3)	0.11496 (17)	−0.06358 (15)	0.0253 (4)
H16	0.8522	0.0684	−0.0952	0.030*
C17	0.7001 (3)	0.13519 (17)	0.05889 (15)	0.0227 (4)
H17	0.8142	0.1011	0.1123	0.027*

	U11	U22	U33	U12	U13	U23
O1	0.0275 (8)	0.0277 (8)	0.0277 (6)	−0.0125 (6)	0.0001 (5)	−0.0083 (6)
N1	0.0208 (8)	0.0226 (9)	0.0161 (7)	−0.0061 (7)	0.0003 (6)	−0.0068 (6)
N2	0.0381 (11)	0.0441 (11)	0.0254 (8)	−0.0143 (8)	0.0003 (7)	−0.0082 (8)
C1	0.0194 (10)	0.0185 (9)	0.0192 (8)	−0.0011 (8)	−0.0035 (7)	−0.0061 (7)
C2	0.0219 (10)	0.0211 (10)	0.0181 (8)	−0.0020 (8)	−0.0005 (7)	−0.0052 (7)
C3	0.0215 (10)	0.0199 (10)	0.0243 (9)	−0.0040 (8)	0.0002 (8)	−0.0052 (7)
C4	0.0269 (11)	0.0283 (11)	0.0262 (9)	−0.0073 (9)	−0.0047 (8)	−0.0105 (8)
C5	0.0316 (11)	0.0274 (11)	0.0179 (8)	−0.0061 (9)	−0.0034 (8)	−0.0058 (8)
C6	0.0207 (10)	0.0218 (10)	0.0169 (8)	−0.0015 (8)	−0.0025 (7)	−0.0049 (7)
C7	0.0239 (11)	0.0213 (10)	0.0182 (8)	−0.0034 (8)	−0.0007 (7)	−0.0036 (7)
C8	0.0196 (10)	0.0210 (10)	0.0210 (9)	−0.0017 (8)	0.0007 (7)	−0.0046 (7)
C9	0.0274 (11)	0.0256 (11)	0.0248 (9)	−0.0066 (9)	0.0001 (8)	−0.0063 (8)
C10	0.0268 (11)	0.0261 (11)	0.0388 (11)	−0.0105 (9)	−0.0085 (8)	−0.0056 (9)
C11	0.0303 (11)	0.0261 (11)	0.0237 (9)	−0.0086 (9)	−0.0048 (8)	−0.0070 (8)
C12	0.0197 (10)	0.0195 (10)	0.0180 (8)	−0.0042 (8)	0.0010 (7)	−0.0057 (7)
C13	0.0210 (10)	0.0241 (11)	0.0265 (9)	0.0005 (8)	−0.0025 (8)	−0.0106 (8)
C14	0.0298 (11)	0.0260 (11)	0.0246 (9)	−0.0039 (9)	−0.0089 (8)	−0.0062 (8)
C15	0.0329 (12)	0.0238 (10)	0.0190 (9)	−0.0065 (9)	−0.0011 (8)	−0.0070 (8)
C16	0.0251 (11)	0.0239 (10)	0.0247 (9)	−0.0023 (8)	0.0011 (8)	−0.0079 (8)
C17	0.0222 (10)	0.0216 (10)	0.0234 (9)	−0.0027 (8)	−0.0040 (8)	−0.0057 (8)

O1—C3	1.3848 (17)	C8—C9	1.491 (2)
O1—C10	1.4367 (17)	C9—H9A	0.9800
N1—C8	1.3891 (18)	C9—H9B	0.9800
N1—C1	1.3984 (19)	C9—H9C	0.9800
N1—C12	1.4428 (18)	C10—H10A	0.9800
N2—C11	1.1491 (17)	C10—H10B	0.9800
C1—C2	1.392 (2)	C10—H10C	0.9800
C1—C6	1.4074 (18)	C12—C17	1.379 (2)
C2—C3	1.384 (2)	C12—C13	1.388 (2)
C2—H2	0.9500	C13—C14	1.388 (2)
C3—C4	1.4028 (19)	C13—H13	0.9500
C4—C5	1.386 (2)	C14—C15	1.383 (2)
C4—H4	0.9500	C14—H14	0.9500
C5—C6	1.394 (2)	C15—C16	1.382 (2)
C5—H5	0.9500	C15—H15	0.9500
C6—C7	1.445 (2)	C16—C17	1.3908 (19)
C7—C8	1.375 (2)	C16—H16	0.9500
C7—C11	1.424 (2)	C17—H17	0.9500
C3—O1—C10	118.09 (12)	H9A—C9—H9B	109.5
C8—N1—C1	109.28 (12)	C8—C9—H9C	109.5
C8—N1—C12	125.76 (13)	H9A—C9—H9C	109.5
C1—N1—C12	124.74 (12)	H9B—C9—H9C	109.5
C2—C1—N1	129.25 (13)	O1—C10—H10A	109.5
C2—C1—C6	122.54 (14)	O1—C10—H10B	109.5
N1—C1—C6	108.17 (13)	H10A—C10—H10B	109.5
C3—C2—C1	117.25 (13)	O1—C10—H10C	109.5
C3—C2—H2	121.4	H10A—C10—H10C	109.5
C1—C2—H2	121.4	H10B—C10—H10C	109.5
C2—C3—O1	115.18 (13)	N2—C11—C7	178.9 (2)
C2—C3—C4	121.71 (14)	C17—C12—C13	121.16 (15)
O1—C3—C4	123.10 (14)	C17—C12—N1	119.28 (15)
C5—C4—C3	119.96 (15)	C13—C12—N1	119.56 (14)
C5—C4—H4	120.0	C14—C13—C12	119.08 (15)
C3—C4—H4	120.0	C14—C13—H13	120.5
C4—C5—C6	119.97 (14)	C12—C13—H13	120.5
C4—C5—H5	120.0	C15—C14—C13	119.90 (16)
C6—C5—H5	120.0	C15—C14—H14	120.0
C5—C6—C1	118.55 (14)	C13—C14—H14	120.0
C5—C6—C7	135.72 (14)	C16—C15—C14	120.69 (15)
C1—C6—C7	105.69 (13)	C16—C15—H15	119.7
C8—C7—C11	123.12 (16)	C14—C15—H15	119.7
C8—C7—C6	108.95 (13)	C15—C16—C17	119.69 (16)
C11—C7—C6	127.90 (15)	C15—C16—H16	120.2
C7—C8—N1	107.91 (14)	C17—C16—H16	120.2
C7—C8—C9	129.08 (14)	C12—C17—C16	119.42 (16)
N1—C8—C9	123.01 (13)	C12—C17—H17	120.3
C8—C9—H9A	109.5	C16—C17—H17	120.3
C8—C9—H9B	109.5
C8—N1—C1—C2	−177.94 (16)	C11—C7—C8—N1	177.40 (15)
C12—N1—C1—C2	7.2 (3)	C6—C7—C8—N1	−0.93 (19)
C8—N1—C1—C6	−0.32 (18)	C11—C7—C8—C9	−3.4 (3)
C12—N1—C1—C6	−175.17 (14)	C6—C7—C8—C9	178.30 (17)
N1—C1—C2—C3	178.75 (16)	C1—N1—C8—C7	0.78 (19)
C6—C1—C2—C3	1.4 (2)	C12—N1—C8—C7	175.56 (15)
C1—C2—C3—O1	178.75 (14)	C1—N1—C8—C9	−178.50 (16)
C1—C2—C3—C4	−1.5 (2)	C12—N1—C8—C9	−3.7 (3)
C10—O1—C3—C2	−173.49 (15)	C8—C7—C11—N2	−83 (10)
C10—O1—C3—C4	6.8 (2)	C6—C7—C11—N2	95 (10)
C2—C3—C4—C5	0.6 (3)	C8—N1—C12—C17	−112.79 (18)
O1—C3—C4—C5	−179.64 (16)	C1—N1—C12—C17	61.2 (2)
C3—C4—C5—C6	0.4 (3)	C8—N1—C12—C13	67.1 (2)
C4—C5—C6—C1	−0.4 (3)	C1—N1—C12—C13	−118.94 (17)
C4—C5—C6—C7	−177.77 (18)	C17—C12—C13—C14	2.7 (2)
C2—C1—C6—C5	−0.5 (2)	N1—C12—C13—C14	−177.16 (14)
N1—C1—C6—C5	−178.30 (15)	C12—C13—C14—C15	−2.4 (2)
C2—C1—C6—C7	177.58 (15)	C13—C14—C15—C16	0.4 (2)
N1—C1—C6—C7	−0.24 (18)	C14—C15—C16—C17	1.5 (2)
C5—C6—C7—C8	178.28 (19)	C13—C12—C17—C16	−0.8 (2)
C1—C6—C7—C8	0.72 (19)	N1—C12—C17—C16	179.00 (14)
C5—C6—C7—C11	0.1 (3)	C15—C16—C17—C12	−1.3 (2)
C1—C6—C7—C11	−177.50 (17)

Cg1, Cg2 and Cg3 are the centroids of the N1/C1/C6–C8, C1–C6 and C12–C17 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9B···Cg2i	0.98	2.78	3.701 (2)	156
C10—H10B···Cg3ii	0.98	2.65	3.516 (2)	148
C10—H10C···Cg1iii	0.98	2.73	3.509 (2)	137

Table 1

Hydrogen-bond geometry (Å, °)

Cg1, Cg2 and Cg3 are the centroids of the N1/C1/C6–C8, C1–C6 and C12–C17 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C9—H9B⋯Cg2i	0.98	2.78	3.701 (2)	156
C10—H10B⋯Cg3ii	0.98	2.65	3.516 (2)	148
C10—H10C⋯Cg1iii	0.98	2.73	3.509 (2)	137

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