2-Methyl-1-phenyl-1H-indole-3-carbo­nitrile

Yang, K.; Li, P.-F.; Liu, Y.; Fang, Z.-Z.

doi:10.1107/S1600536811039250

organic compounds

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Volume 67| Part 11| November 2011| Page o2902

doi:10.1107/S1600536811039250

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2-Methyl-1-phenyl-1H-indole-3-carbonitrile

Kun Yang,^a ^* Pei-Fan Li,^b Yan Liu ^b and Zhi-Zhong Fang ^a

^aTeaching & Research Center, Tianjin Medical University, Tianjin 300070, People's Republic of China, and ^bPharmacy Department, Tianjin Medical College, Tianjin 300222, People's Republic of China
^*Correspondence e-mail: tijmu@tijmu.edu.cn

(Received 21 September 2011; accepted 24 September 2011; online 8 October 2011)

In the title compound, C₁₆H₁₂N₂, 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 interactions.

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_r = 232.28
Triclinic, $[P \overline 1]$
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[F² > 2σ(F²)] = 0.044
wR(F²) = 0.120
S = 0.98
3494 reflections
164 parameters
H-atom parameters constrained
Δρ_max = 0.45 e Å⁻³
Δρ_min = −0.29 e Å⁻³

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) -x+2, -y+1, -z; (ii) x-1, y, z; (iii) -x+1, -y+1, -z.

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.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811039250/hb6411sup1.cif

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

Supporting information file. DOI: 10.1107/S1600536811039250/hb6411Isup3.cml

checkCIF report

Comment top

Indoles are an important compound possessing pharmaceutical properties. Extensive investigation on the crystal structures of indoles helps disclose their structure-activity relationship. For continuing our reseach, herein, we reported the crystal structure of the title indole derivative, (I).

In the molecular structure (Fig. 1), the components of the indole ring system are almost coplanar with a dihedral angle of 0.89 (7)° between its pyrrole part and benzene part. The indole ring forms an angle of 64.92 (5)° with the benzene ring.

In the molecular packing, π-π stacking and C—H···π interactions were observed, helping solidify the packing.

Related literature top

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 top

The title compound was prepared according to the method of the literature (Du et al., 2006). Colourless prisms of (I) were grown from a mixture of ethyl actate and petroleum ether.

Computing details top

Data collection: CrystalClear-SM Expert (Rigaku 2009); cell refinement: CrystalClear-SM Expert (Rigaku 2009); data reduction: CrystalClear-SM Expert (Rigaku 2009); 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 (Rigaku, 2009).

Figures top

Fig. 1. The molecular structure of (I) with 50% probability displacement ellipsoids.

2-Methyl-1-phenyl-1H-indole-3-carbonitrile top

Crystal data top

C₁₆H₁₂N₂	Z = 2
M_r = 232.28	F(000) = 244
Triclinic, P1	D_x = 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

Data collection top

Rigaku Saturn724 CCD diffractometer	3494 independent reflections
Radiation source: rotating anode	2309 reflections with I > 2σ(I)
Multilayer monochromator	R_int = 0.040
Detector resolution: 14.222 pixels mm^-1	θ_max = 30.0°, θ_min = 2.1°
ω scans	h = −8→8
Absorption correction: multi-scan (CrystalClear-SM Expert; Rigaku, 2009)	k = −13→13
T_min = 0.980, T_max = 0.995	l = −15→15
11425 measured reflections

Refinement top

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(F_o²) + (0.0674P)²] where P = (F_o² + 2F_c²)/3
3494 reflections	(Δ/σ)_max = 0.002
164 parameters	Δρ_max = 0.45 e Å⁻³
0 restraints	Δρ_min = −0.29 e Å⁻³

Crystal data top

C₁₆H₁₂N₂	γ = 88.13 (2)°
M_r = 232.28	V = 599.34 (14) Å³
Triclinic, P1	Z = 2
a = 6.3610 (5) Å	Mo Kα radiation
b = 9.497 (1) Å	µ = 0.08 mm⁻¹
c = 11.0210 (12) Å	T = 113 K
α = 65.97 (2)°	0.26 × 0.24 × 0.06 mm
β = 80.52 (2)°

Data collection top

Rigaku Saturn724 CCD diffractometer	3494 independent reflections
Absorption correction: multi-scan (CrystalClear-SM Expert; Rigaku, 2009)	2309 reflections with I > 2σ(I)
T_min = 0.980, T_max = 0.995	R_int = 0.040
11425 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.044	0 restraints
wR(F²) = 0.120	H-atom parameters constrained
S = 0.98	Δρ_max = 0.45 e Å⁻³
3494 reflections	Δρ_min = −0.29 e Å⁻³
164 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) −x+2, −y+1, −z; (ii) x−1, y, z; (iii) −x+1, −y+1, −z.

Experimental details

Crystal data
Chemical formula	C₁₆H₁₂N₂
M_r	232.28
Crystal system, space group	Triclinic, P1
Temperature (K)	113
a, b, c (Å)	6.3610 (5), 9.497 (1), 11.0210 (12)
α, β, γ (°)	65.97 (2), 80.52 (2), 88.13 (2)
V (Å³)	599.34 (14)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.26 × 0.24 × 0.06

Data collection
Diffractometer	Rigaku Saturn724 CCD diffractometer
Absorption correction	Multi-scan (CrystalClear-SM Expert; Rigaku, 2009)
T_min, T_max	0.980, 0.995
No. of measured, independent and observed [I > 2σ(I)] reflections	11425, 3494, 2309
R_int	0.040
(sin θ/λ)_max (Å⁻¹)	0.704

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.044, 0.120, 0.98
No. of reflections	3494
No. of parameters	164
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.45, −0.29

Computer programs: CrystalClear-SM Expert (Rigaku 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), CrystalStructure (Rigaku, 2009).

Hydrogen-bond geometry (Å, º) top

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) −x+2, −y+1, −z; (ii) x−1, y, z; (iii) −x+1, −y+1, −z.

References

Du, Y., Liu, R., Linn, G. & Zhao, K. (2006). Org. Lett. 8, 5919–5922. Web of Science CSD CrossRef PubMed CAS Google Scholar
Jin, H., Li, P., Liu, B. & Cheng, X. (2009). Acta Cryst. E65, o236. Web of Science CSD CrossRef IUCr Journals Google Scholar
Rigaku (2009). CrystalClear-SM Expert and CrystalStructure. Rigaku Corporation, Tokyo, Japan. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Yan, Q. & Qi, X. (2011a). Acta Cryst. E67, o2312. Web of Science CSD CrossRef IUCr Journals Google Scholar
Yan, Q. & Qi, X. (2011b). Acta Cryst. E67, o2509. Web of Science CSD CrossRef IUCr Journals Google Scholar
Yang, K., Li, P.-F., Liu, Y. & Fang, Z.-Z. (2011). Acta Cryst. E67, o1041. Web of Science CSD CrossRef IUCr Journals Google Scholar

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doi:10.1107/S1600536811039250

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