1-(4-Meth­oxy­phen­yl)-2-methyl-1H-indole-3-carbonitrile

Yan, Q.; Qi, X.

doi:10.1107/S1600536811031035

organic compounds

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ISSN: 2056-9890

Volume 67| Part 9| September 2011| Page o2312

doi:10.1107/S1600536811031035

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1-(4-Methoxyphenyl)-2-methyl-1H-indole-3-carbonitrile

Qiao Yan ^a and Xiuxiang Qi ^a ^*

^aSchool of Pharmaceutical Science and Technology, Tianjin University, Tianjin 300072, People's Republic of China
^*Correspondence e-mail: qxx@zzu.edu.cn

(Received 22 July 2011; accepted 2 August 2011; online 11 August 2011)

In the title compound, C₁₇H₁₄N₂O, the dihedral angle between the indole ring system and the benzene ring is 58.41 (4)°. The crystal packing features π–π stacking [shortest centroid–centroid separation = 3.8040 (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 a related structure, see: Yang et al. (2011 ).

Experimental

Crystal data

C₁₇H₁₄N₂O
M_r = 262.30
Triclinic, $[P \overline 1]$
a = 7.7381 (10) Å
b = 9.4598 (14) Å
c = 9.7976 (16) Å
α = 95.983 (2)°
β = 95.464 (4)°
γ = 106.295 (5)°
V = 678.79 (17) Å³
Z = 2
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 113 K
0.20 × 0.18 × 0.16 mm

Data collection

Rigaku Saturn724 CCD diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku, 2009 ) T_min = 0.984, T_max = 0.987
8580 measured reflections
3210 independent reflections
2146 reflections with I > 2σ(I)
R_int = 0.035

Refinement

R[F² > 2σ(F²)] = 0.035
wR(F²) = 0.090
S = 1.01
3210 reflections
183 parameters
H-atom parameters constrained
Δρ_max = 0.19 e Å⁻³
Δρ_min = −0.24 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg2 and Cg3 are the centroids of the C2–C7 and C8–C13 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯Cg3ⁱ	0.95	2.83	3.6542 (14)	146
C10—H10⋯Cg2ⁱⁱ	0.95	2.95	3.7133 (14)	138
Symmetry codes: (i) x-1, y, z; (ii) -x+1, -y+1, -z+2.

Data collection: CrystalClear (Rigaku, 2009); cell refinement: CrystalClear; data reduction: CrystalClear; 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/S1600536811031035/hb6329sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811031035/hb6329Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811031035/hb6329Isup3.cml

checkCIF report

Comment top

In the molecular structure of the title compound, (I), (Fig. 1), the indole ring is almost planar with a dihedral angle of 2.66 (6)° between its pyrrole ring and fused benzene ring, which is greater than that [0.85 (6)°] of the 1-(2-chlorophenyl)- 6-fluoro-2-methyl-1H-indole-3-carbonitrile reported by Yang et al. (2011). The indole ring constructs an angle of 58.41 (4) ° with the methoxylbenzene ring, which is much less than that [80.91 (5)°] reported by Yang et al. (2011).

In the crystal packing, π-π stacking interaction and C—H···π interaction help establish the molecular packing. The shortest centroid-centroid separation is 3.8040 (9) Å, which occurs between the benzo part and pyrrole part of the molecules.

Related literature top

For the synthesis of the title compound, see: Du et al. (2006). For its precursor, see: Jin et al. (2009). For a related structure, see: Yang et al. (2011).

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 (Rigaku, 2009); cell refinement: CrystalClear (Rigaku, 2009); data reduction: CrystalClear (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 molecule one of (I) with 50% probability displacement ellipsoids.

1-(4-Methoxyphenyl)-2-methyl-1H-indole-3-carbonitrile top

Crystal data top

C₁₇H₁₄N₂O	Z = 2
M_r = 262.30	F(000) = 276
Triclinic, P1	D_x = 1.283 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.7381 (10) Å	Cell parameters from 2366 reflections
b = 9.4598 (14) Å	θ = 2.1–27.9°
c = 9.7976 (16) Å	µ = 0.08 mm⁻¹
α = 95.983 (2)°	T = 113 K
β = 95.464 (4)°	Prism, colorless
γ = 106.295 (5)°	0.20 × 0.18 × 0.16 mm
V = 678.79 (17) Å³

Data collection top

Rigaku Saturn724 CCD diffractometer	3210 independent reflections
Radiation source: rotating anode	2146 reflections with I > 2σ(I)
Multilayer monochromator	R_int = 0.035
Detector resolution: 14.22 pixels mm^-1	θ_max = 27.9°, θ_min = 2.1°
ω and ϕ scans	h = −10→10
Absorption correction: multi-scan (CrystalClear; Rigaku, 2009)	k = −12→12
T_min = 0.984, T_max = 0.987	l = −12→12
8580 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)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.090	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.038P)²] where P = (F_o² + 2F_c²)/3
3210 reflections	(Δ/σ)_max = 0.001
183 parameters	Δρ_max = 0.19 e Å⁻³
0 restraints	Δρ_min = −0.24 e Å⁻³

Crystal data top

C₁₇H₁₄N₂O	γ = 106.295 (5)°
M_r = 262.30	V = 678.79 (17) Å³
Triclinic, P1	Z = 2
a = 7.7381 (10) Å	Mo Kα radiation
b = 9.4598 (14) Å	µ = 0.08 mm⁻¹
c = 9.7976 (16) Å	T = 113 K
α = 95.983 (2)°	0.20 × 0.18 × 0.16 mm
β = 95.464 (4)°

Data collection top

Rigaku Saturn724 CCD diffractometer	3210 independent reflections
Absorption correction: multi-scan (CrystalClear; Rigaku, 2009)	2146 reflections with I > 2σ(I)
T_min = 0.984, T_max = 0.987	R_int = 0.035
8580 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.035	0 restraints
wR(F²) = 0.090	H-atom parameters constrained
S = 1.01	Δρ_max = 0.19 e Å⁻³
3210 reflections	Δρ_min = −0.24 e Å⁻³
183 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
O1	1.23428 (10)	0.89022 (9)	0.06414 (8)	0.0300 (2)
N1	0.63352 (12)	0.69683 (10)	0.34222 (9)	0.0207 (2)
N2	0.27094 (14)	0.77814 (11)	0.68887 (10)	0.0350 (3)
C1	1.34704 (16)	0.79705 (15)	0.03434 (14)	0.0386 (3)
H1A	1.3990	0.7732	0.1211	0.058*
H1B	1.4452	0.8492	−0.0148	0.058*
H1C	1.2741	0.7050	−0.0237	0.058*
C2	1.08888 (14)	0.83382 (12)	0.13188 (11)	0.0223 (3)
C3	1.04548 (15)	0.69409 (12)	0.17549 (11)	0.0246 (3)
H3	1.1173	0.6293	0.1573	0.030*
C4	0.89572 (14)	0.65052 (12)	0.24598 (11)	0.0241 (3)
H4	0.8661	0.5558	0.2771	0.029*
C5	0.78939 (14)	0.74363 (12)	0.27134 (11)	0.0207 (2)
C6	0.83139 (14)	0.88247 (12)	0.22493 (11)	0.0221 (2)
H6	0.7570	0.9457	0.2400	0.026*
C7	0.98146 (14)	0.92716 (12)	0.15712 (11)	0.0226 (2)
H7	1.0119	1.0225	0.1274	0.027*
C8	0.48670 (14)	0.57024 (11)	0.29653 (11)	0.0199 (2)
C9	0.45885 (14)	0.46469 (12)	0.17956 (11)	0.0239 (3)
H9	0.5482	0.4695	0.1186	0.029*
C10	0.29541 (15)	0.35277 (13)	0.15628 (12)	0.0279 (3)
H10	0.2715	0.2794	0.0774	0.033*
C11	0.16419 (15)	0.34554 (12)	0.24707 (12)	0.0273 (3)
H11	0.0531	0.2676	0.2283	0.033*
C12	0.19364 (15)	0.44962 (12)	0.36305 (12)	0.0235 (3)
H12	0.1051	0.4429	0.4248	0.028*
C13	0.35650 (14)	0.56517 (12)	0.38782 (11)	0.0205 (2)
C14	0.42996 (15)	0.69530 (12)	0.48926 (11)	0.0216 (2)
C15	0.59797 (14)	0.77272 (12)	0.45929 (11)	0.0213 (2)
C16	0.72912 (15)	0.91064 (12)	0.53687 (11)	0.0293 (3)
H16A	0.7311	0.9943	0.4852	0.044*
H16B	0.8506	0.8976	0.5486	0.044*
H16C	0.6920	0.9310	0.6280	0.044*
C17	0.34392 (15)	0.74071 (12)	0.60128 (12)	0.0246 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0284 (4)	0.0321 (5)	0.0346 (5)	0.0114 (4)	0.0121 (4)	0.0123 (4)
N1	0.0221 (5)	0.0197 (5)	0.0199 (5)	0.0056 (4)	0.0027 (4)	0.0018 (4)
N2	0.0394 (6)	0.0346 (6)	0.0341 (6)	0.0142 (5)	0.0124 (5)	0.0027 (5)
C1	0.0320 (7)	0.0475 (8)	0.0473 (8)	0.0209 (6)	0.0166 (6)	0.0203 (7)
C2	0.0222 (6)	0.0251 (6)	0.0184 (6)	0.0054 (5)	0.0012 (5)	0.0034 (5)
C3	0.0247 (6)	0.0267 (6)	0.0265 (6)	0.0128 (5)	0.0033 (5)	0.0070 (5)
C4	0.0266 (6)	0.0217 (6)	0.0255 (6)	0.0086 (5)	0.0018 (5)	0.0073 (5)
C5	0.0208 (5)	0.0225 (6)	0.0179 (5)	0.0057 (5)	0.0006 (4)	0.0024 (4)
C6	0.0259 (6)	0.0199 (6)	0.0203 (6)	0.0085 (5)	0.0002 (5)	0.0000 (5)
C7	0.0282 (6)	0.0178 (6)	0.0200 (6)	0.0048 (5)	0.0010 (5)	0.0019 (4)
C8	0.0208 (5)	0.0183 (5)	0.0212 (6)	0.0072 (4)	0.0000 (4)	0.0041 (4)
C9	0.0268 (6)	0.0237 (6)	0.0226 (6)	0.0098 (5)	0.0032 (5)	0.0024 (5)
C10	0.0307 (6)	0.0223 (6)	0.0287 (7)	0.0077 (5)	0.0005 (5)	−0.0022 (5)
C11	0.0238 (6)	0.0201 (6)	0.0361 (7)	0.0055 (5)	0.0001 (5)	0.0016 (5)
C12	0.0234 (6)	0.0219 (6)	0.0284 (6)	0.0098 (5)	0.0050 (5)	0.0067 (5)
C13	0.0237 (6)	0.0193 (5)	0.0209 (6)	0.0104 (5)	0.0011 (5)	0.0039 (4)
C14	0.0261 (6)	0.0216 (6)	0.0195 (6)	0.0107 (5)	0.0027 (4)	0.0038 (5)
C15	0.0262 (6)	0.0203 (6)	0.0184 (6)	0.0091 (5)	0.0014 (4)	0.0023 (4)
C16	0.0339 (6)	0.0258 (6)	0.0243 (6)	0.0046 (5)	0.0023 (5)	−0.0006 (5)
C17	0.0279 (6)	0.0213 (6)	0.0258 (6)	0.0090 (5)	0.0028 (5)	0.0040 (5)

Geometric parameters (Å, º) top

O1—C2	1.3675 (12)	C7—H7	0.9500
O1—C1	1.4317 (13)	C8—C9	1.3965 (14)
N1—C15	1.3805 (13)	C8—C13	1.4038 (14)
N1—C8	1.3976 (13)	C9—C10	1.3842 (15)
N1—C5	1.4342 (13)	C9—H9	0.9500
N2—C17	1.1497 (13)	C10—C11	1.4045 (15)
C1—H1A	0.9800	C10—H10	0.9500
C1—H1B	0.9800	C11—C12	1.3799 (15)
C1—H1C	0.9800	C11—H11	0.9500
C2—C7	1.3919 (15)	C12—C13	1.3984 (15)
C2—C3	1.3923 (15)	C12—H12	0.9500
C3—C4	1.3905 (15)	C13—C14	1.4391 (15)
C3—H3	0.9500	C14—C15	1.3770 (15)
C4—C5	1.3837 (14)	C14—C17	1.4261 (15)
C4—H4	0.9500	C15—C16	1.4877 (15)
C5—C6	1.3966 (14)	C16—H16A	0.9800
C6—C7	1.3779 (14)	C16—H16B	0.9800
C6—H6	0.9500	C16—H16C	0.9800

C2—O1—C1	117.18 (9)	N1—C8—C13	108.14 (9)
C15—N1—C8	109.22 (9)	C10—C9—C8	117.08 (10)
C15—N1—C5	126.23 (9)	C10—C9—H9	121.5
C8—N1—C5	124.42 (9)	C8—C9—H9	121.5
O1—C1—H1A	109.5	C9—C10—C11	121.28 (10)
O1—C1—H1B	109.5	C9—C10—H10	119.4
H1A—C1—H1B	109.5	C11—C10—H10	119.4
O1—C1—H1C	109.5	C12—C11—C10	121.21 (11)
H1A—C1—H1C	109.5	C12—C11—H11	119.4
H1B—C1—H1C	109.5	C10—C11—H11	119.4
O1—C2—C7	115.32 (10)	C11—C12—C13	118.65 (11)
O1—C2—C3	124.61 (10)	C11—C12—H12	120.7
C7—C2—C3	120.07 (10)	C13—C12—H12	120.7
C4—C3—C2	119.16 (10)	C12—C13—C8	119.40 (10)
C4—C3—H3	120.4	C12—C13—C14	134.75 (10)
C2—C3—H3	120.4	C8—C13—C14	105.80 (10)
C5—C4—C3	120.69 (10)	C15—C14—C17	124.72 (10)
C5—C4—H4	119.7	C15—C14—C13	108.77 (9)
C3—C4—H4	119.7	C17—C14—C13	126.50 (10)
C4—C5—C6	119.91 (10)	C14—C15—N1	108.06 (10)
C4—C5—N1	120.31 (10)	C14—C15—C16	128.79 (10)
C6—C5—N1	119.76 (10)	N1—C15—C16	123.11 (10)
C7—C6—C5	119.59 (10)	C15—C16—H16A	109.5
C7—C6—H6	120.2	C15—C16—H16B	109.5
C5—C6—H6	120.2	H16A—C16—H16B	109.5
C6—C7—C2	120.56 (10)	C15—C16—H16C	109.5
C6—C7—H7	119.7	H16A—C16—H16C	109.5
C2—C7—H7	119.7	H16B—C16—H16C	109.5
C9—C8—N1	129.45 (10)	N2—C17—C14	178.02 (12)
C9—C8—C13	122.36 (10)

C1—O1—C2—C7	−179.16 (9)	C9—C10—C11—C12	−0.16 (17)
C1—O1—C2—C3	1.16 (16)	C10—C11—C12—C13	1.13 (17)
O1—C2—C3—C4	178.73 (9)	C11—C12—C13—C8	−1.51 (16)
C7—C2—C3—C4	−0.94 (16)	C11—C12—C13—C14	175.65 (11)
C2—C3—C4—C5	0.76 (16)	C9—C8—C13—C12	0.98 (16)
C3—C4—C5—C6	0.52 (16)	N1—C8—C13—C12	178.74 (9)
C3—C4—C5—N1	179.03 (9)	C9—C8—C13—C14	−176.92 (9)
C15—N1—C5—C4	125.90 (12)	N1—C8—C13—C14	0.84 (11)
C8—N1—C5—C4	−58.75 (14)	C12—C13—C14—C15	−178.10 (11)
C15—N1—C5—C6	−55.59 (14)	C8—C13—C14—C15	−0.67 (12)
C8—N1—C5—C6	119.76 (11)	C12—C13—C14—C17	0.6 (2)
C4—C5—C6—C7	−1.62 (15)	C8—C13—C14—C17	178.00 (10)
N1—C5—C6—C7	179.86 (9)	C17—C14—C15—N1	−178.46 (10)
C5—C6—C7—C2	1.45 (16)	C13—C14—C15—N1	0.24 (12)
O1—C2—C7—C6	−179.86 (9)	C17—C14—C15—C16	3.84 (18)
C3—C2—C7—C6	−0.16 (16)	C13—C14—C15—C16	−177.46 (10)
C15—N1—C8—C9	176.83 (10)	C8—N1—C15—C14	0.29 (12)
C5—N1—C8—C9	0.80 (17)	C5—N1—C15—C14	176.23 (9)
C15—N1—C8—C13	−0.72 (12)	C8—N1—C15—C16	178.15 (9)
C5—N1—C8—C13	−176.75 (9)	C5—N1—C15—C16	−5.91 (16)
N1—C8—C9—C10	−177.26 (10)	C15—C14—C17—N2	110 (4)
C13—C8—C9—C10	−0.01 (16)	C13—C14—C17—N2	−68 (4)
C8—C9—C10—C11	−0.40 (16)

Hydrogen-bond geometry (Å, º) top

Cg2 and Cg3 are the centroids of the C2–C7 and C8–C13 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···Cg3ⁱ	0.95	2.83	3.6542 (14)	146
C10—H10···Cg2ⁱⁱ	0.95	2.95	3.7133 (14)	138

Symmetry codes: (i) x−1, y, z; (ii) −x+1, −y+1, −z+2.

Experimental details

Crystal data
Chemical formula	C₁₇H₁₄N₂O
M_r	262.30
Crystal system, space group	Triclinic, P1
Temperature (K)	113
a, b, c (Å)	7.7381 (10), 9.4598 (14), 9.7976 (16)
α, β, γ (°)	95.983 (2), 95.464 (4), 106.295 (5)
V (Å³)	678.79 (17)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.20 × 0.18 × 0.16

Data collection
Diffractometer	Rigaku Saturn724 CCD diffractometer
Absorption correction	Multi-scan (CrystalClear; Rigaku, 2009)
T_min, T_max	0.984, 0.987
No. of measured, independent and observed [I > 2σ(I)] reflections	8580, 3210, 2146
R_int	0.035
(sin θ/λ)_max (Å⁻¹)	0.658

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.035, 0.090, 1.01
No. of reflections	3210
No. of parameters	183
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.19, −0.24

Computer programs: CrystalClear (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 C2–C7 and C8–C13 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···Cg3ⁱ	0.95	2.83	3.6542 (14)	146
C10—H10···Cg2ⁱⁱ	0.95	2.95	3.7133 (14)	138

Symmetry codes: (i) x−1, y, z; (ii) −x+1, −y+1, −z+2.

Acknowledgements

XQ is grateful for financial support for this project from the China Postdoctoral Science Foundation (200904507610).

References

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ISSN: 2056-9890

Volume 67| Part 9| September 2011| Page o2312

doi:10.1107/S1600536811031035

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