1-(4-Bromo-phen-yl)-2-methyl-1H-indole-3-carbonitrile.

In the title compound, C(16)H(11)BrN(2), the dihedral angle between the indole ring system and the phenyl ring is 58.85 (11)°.

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 (2011 ▶).

Experimental

Crystal data

C16H11BrN2

M = 311.18

Monoclinic,

a = 9.170 (7) Å

b = 8.849 (6) Å

c = 16.337 (12) Å

β = 94.415 (15)°

V = 1321.7 (16) Å3

Z = 4

Mo Kα radiation

μ = 3.10 mm−1

T = 113 K

0.20 × 0.18 × 0.14 mm

Data collection

Rigaku Saturn724 CCD diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku, 2009 ▶) T min = 0.576, T max = 0.671

12992 measured reflections

3147 independent reflections

2309 reflections with I > 2σ(I)

R int = 0.052

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.106

S = 1.00

3147 reflections

173 parameters

H-atom parameters constrained

Δρmax = 0.90 e Å−3

Δρmin = −0.73 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/S1600536811034246/hb6373sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811034246/hb6373Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811034246/hb6373Isup3.cml

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

C16H11BrN2	F(000) = 624
Mr = 311.18	Dx = 1.564 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 4781 reflections
a = 9.170 (7) Å	θ = 2.2–27.9°
b = 8.849 (6) Å	µ = 3.10 mm−1
c = 16.337 (12) Å	T = 113 K
β = 94.415 (15)°	Prism, colorless
V = 1321.7 (16) Å3	0.20 × 0.18 × 0.14 mm
Z = 4

Rigaku Saturn724 CCD diffractometer	3147 independent reflections
Radiation source: rotating anode	2309 reflections with I > 2σ(I)
multilayer	Rint = 0.052
Detector resolution: 14.22 pixels mm-1	θmax = 27.9°, θmin = 2.5°
ω and φ scans	h = −12→11
Absorption correction: multi-scan (CrystalClear; Rigaku, 2009)	k = −11→11
Tmin = 0.576, Tmax = 0.671	l = −21→21
12992 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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.106	H-atom parameters constrained
S = 1.00	w = 1/[σ2(Fo2) + (0.0495P)2] where P = (Fo2 + 2Fc2)/3
3147 reflections	(Δ/σ)max < 0.001
173 parameters	Δρmax = 0.90 e Å−3
0 restraints	Δρmin = −0.73 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
Br1	1.31610 (4)	0.01069 (4)	0.08227 (2)	0.03260 (14)
N1	0.8376 (3)	0.4726 (3)	0.12974 (16)	0.0204 (6)
N2	0.3390 (3)	0.6165 (3)	0.11113 (18)	0.0341 (7)
C1	1.1681 (3)	0.1574 (3)	0.0968 (2)	0.0229 (7)
C2	1.1611 (4)	0.2252 (3)	0.1735 (2)	0.0248 (7)
H2	1.2302	0.2002	0.2178	0.030*
C3	1.0509 (4)	0.3301 (3)	0.18380 (19)	0.0243 (7)
H3	1.0444	0.3783	0.2354	0.029*
C4	0.9508 (3)	0.3642 (3)	0.11868 (19)	0.0205 (6)
C5	0.9610 (3)	0.2969 (3)	0.04233 (19)	0.0215 (7)
H5	0.8934	0.3230	−0.0024	0.026*
C6	1.0702 (3)	0.1913 (3)	0.0317 (2)	0.0236 (7)
H6	1.0770	0.1434	−0.0199	0.028*
C7	0.8620 (3)	0.6253 (3)	0.15065 (18)	0.0198 (6)
C8	0.9938 (3)	0.6992 (3)	0.17217 (18)	0.0225 (7)
H8	1.0846	0.6470	0.1749	0.027*
C9	0.9861 (4)	0.8520 (3)	0.18934 (19)	0.0250 (7)
H9	1.0732	0.9057	0.2058	0.030*
C10	0.8526 (4)	0.9285 (4)	0.18296 (19)	0.0264 (7)
H10	0.8513	1.0340	0.1938	0.032*
C11	0.7227 (4)	0.8555 (3)	0.16141 (18)	0.0236 (7)
H11	0.6327	0.9093	0.1574	0.028*
C12	0.7265 (3)	0.6991 (3)	0.14552 (18)	0.0206 (7)
C13	0.6191 (3)	0.5860 (3)	0.12233 (18)	0.0219 (7)
C14	0.6892 (3)	0.4497 (3)	0.11365 (19)	0.0218 (7)
C15	0.6229 (4)	0.2960 (3)	0.0985 (2)	0.0283 (8)
H15A	0.6327	0.2370	0.1494	0.042*
H15B	0.6736	0.2440	0.0560	0.042*
H15C	0.5190	0.3068	0.0803	0.042*
C16	0.4642 (4)	0.6019 (3)	0.11543 (19)	0.0245 (7)

	U11	U22	U33	U12	U13	U23
Br1	0.02374 (19)	0.0305 (2)	0.0430 (2)	0.01071 (15)	−0.00149 (15)	−0.00554 (15)
N1	0.0142 (12)	0.0235 (14)	0.0236 (14)	0.0045 (10)	0.0013 (11)	−0.0011 (10)
N2	0.0214 (16)	0.0380 (17)	0.0430 (18)	0.0044 (13)	0.0025 (14)	−0.0032 (13)
C1	0.0152 (15)	0.0197 (15)	0.0338 (18)	0.0052 (13)	0.0009 (13)	−0.0005 (13)
C2	0.0201 (16)	0.0257 (17)	0.0273 (17)	0.0019 (14)	−0.0059 (14)	0.0001 (13)
C3	0.0238 (17)	0.0261 (16)	0.0229 (17)	0.0023 (14)	0.0007 (14)	−0.0023 (12)
C4	0.0144 (15)	0.0214 (16)	0.0260 (16)	0.0040 (12)	0.0029 (13)	0.0004 (12)
C5	0.0185 (16)	0.0249 (16)	0.0211 (16)	0.0032 (13)	0.0018 (13)	−0.0012 (12)
C6	0.0219 (17)	0.0252 (16)	0.0238 (17)	0.0020 (13)	0.0017 (14)	−0.0027 (12)
C7	0.0184 (16)	0.0219 (16)	0.0194 (15)	0.0016 (13)	0.0031 (13)	−0.0001 (12)
C8	0.0164 (16)	0.0262 (17)	0.0249 (17)	0.0029 (13)	0.0021 (13)	0.0000 (12)
C9	0.0222 (18)	0.0271 (17)	0.0254 (17)	−0.0042 (14)	0.0004 (14)	0.0013 (13)
C10	0.0339 (19)	0.0220 (16)	0.0236 (17)	0.0031 (15)	0.0045 (15)	−0.0014 (12)
C11	0.0215 (17)	0.0245 (17)	0.0254 (17)	0.0059 (13)	0.0059 (14)	0.0000 (12)
C12	0.0190 (16)	0.0221 (16)	0.0211 (16)	0.0035 (13)	0.0039 (13)	0.0011 (12)
C13	0.0165 (15)	0.0259 (16)	0.0237 (16)	0.0034 (13)	0.0044 (13)	0.0022 (12)
C14	0.0180 (16)	0.0261 (16)	0.0216 (16)	−0.0003 (13)	0.0024 (13)	−0.0003 (12)
C15	0.0212 (17)	0.0278 (18)	0.036 (2)	0.0005 (14)	0.0003 (15)	−0.0058 (14)
C16	0.0201 (17)	0.0251 (17)	0.0283 (17)	0.0010 (14)	0.0019 (14)	−0.0014 (13)

Br1—C1	1.906 (3)	C7—C12	1.401 (4)
N1—C14	1.381 (4)	C8—C9	1.384 (4)
N1—C7	1.408 (4)	C8—H8	0.9500
N1—C4	1.435 (4)	C9—C10	1.396 (4)
N2—C16	1.152 (4)	C9—H9	0.9500
C1—C6	1.371 (4)	C10—C11	1.377 (4)
C1—C2	1.396 (4)	C10—H10	0.9500
C2—C3	1.393 (4)	C11—C12	1.410 (4)
C2—H2	0.9500	C11—H11	0.9500
C3—C4	1.384 (4)	C12—C13	1.434 (4)
C3—H3	0.9500	C13—C14	1.379 (4)
C4—C5	1.392 (4)	C13—C16	1.423 (4)
C5—C6	1.391 (4)	C14—C15	1.503 (4)
C5—H5	0.9500	C15—H15A	0.9800
C6—H6	0.9500	C15—H15B	0.9800
C7—C8	1.395 (4)	C15—H15C	0.9800
C14—N1—C7	108.8 (2)	C7—C8—H8	121.6
C14—N1—C4	126.1 (3)	C8—C9—C10	121.1 (3)
C7—N1—C4	124.7 (3)	C8—C9—H9	119.4
C6—C1—C2	122.1 (3)	C10—C9—H9	119.4
C6—C1—Br1	118.8 (2)	C11—C10—C9	121.9 (3)
C2—C1—Br1	119.1 (2)	C11—C10—H10	119.1
C3—C2—C1	118.6 (3)	C9—C10—H10	119.1
C3—C2—H2	120.7	C10—C11—C12	118.3 (3)
C1—C2—H2	120.7	C10—C11—H11	120.8
C4—C3—C2	119.8 (3)	C12—C11—H11	120.8
C4—C3—H3	120.1	C7—C12—C11	118.7 (3)
C2—C3—H3	120.1	C7—C12—C13	106.2 (3)
C3—C4—C5	120.6 (3)	C11—C12—C13	135.1 (3)
C3—C4—N1	119.5 (3)	C14—C13—C16	123.2 (3)
C5—C4—N1	119.9 (3)	C14—C13—C12	108.8 (3)
C6—C5—C4	119.9 (3)	C16—C13—C12	127.8 (3)
C6—C5—H5	120.0	C13—C14—N1	108.2 (3)
C4—C5—H5	120.0	C13—C14—C15	128.5 (3)
C1—C6—C5	119.0 (3)	N1—C14—C15	123.0 (3)
C1—C6—H6	120.5	C14—C15—H15A	109.5
C5—C6—H6	120.5	C14—C15—H15B	109.5
C8—C7—C12	123.0 (3)	H15A—C15—H15B	109.5
C8—C7—N1	129.0 (3)	C14—C15—H15C	109.5
C12—C7—N1	108.0 (3)	H15A—C15—H15C	109.5
C9—C8—C7	116.9 (3)	H15B—C15—H15C	109.5
C9—C8—H8	121.6	N2—C16—C13	178.7 (4)
C6—C1—C2—C3	0.1 (5)	C9—C10—C11—C12	0.0 (5)
Br1—C1—C2—C3	−178.9 (2)	C8—C7—C12—C11	1.1 (5)
C1—C2—C3—C4	0.4 (5)	N1—C7—C12—C11	−178.1 (3)
C2—C3—C4—C5	−1.4 (5)	C8—C7—C12—C13	−179.8 (3)
C2—C3—C4—N1	−179.9 (3)	N1—C7—C12—C13	1.0 (3)
C14—N1—C4—C3	−125.7 (3)	C10—C11—C12—C7	−1.3 (4)
C7—N1—C4—C3	61.5 (4)	C10—C11—C12—C13	179.9 (3)
C14—N1—C4—C5	55.8 (4)	C7—C12—C13—C14	−0.3 (3)
C7—N1—C4—C5	−117.1 (3)	C11—C12—C13—C14	178.6 (3)
C3—C4—C5—C6	1.7 (5)	C7—C12—C13—C16	174.7 (3)
N1—C4—C5—C6	−179.7 (3)	C11—C12—C13—C16	−6.4 (6)
C2—C1—C6—C5	0.2 (5)	C16—C13—C14—N1	−175.8 (3)
Br1—C1—C6—C5	179.2 (2)	C12—C13—C14—N1	−0.6 (3)
C4—C5—C6—C1	−1.1 (5)	C16—C13—C14—C15	−2.0 (5)
C14—N1—C7—C8	179.4 (3)	C12—C13—C14—C15	173.2 (3)
C4—N1—C7—C8	−6.7 (5)	C7—N1—C14—C13	1.2 (3)
C14—N1—C7—C12	−1.4 (3)	C4—N1—C14—C13	−172.6 (3)
C4—N1—C7—C12	172.5 (3)	C7—N1—C14—C15	−173.0 (3)
C12—C7—C8—C9	0.4 (5)	C4—N1—C14—C15	13.2 (5)
N1—C7—C8—C9	179.5 (3)	C14—C13—C16—N2	136 (18)
C7—C8—C9—C10	−1.8 (5)	C12—C13—C16—N2	−38 (18)
C8—C9—C10—C11	1.6 (5)