(4-Bromo-phen-yl)(1H-indol-7-yl)methanone.

In the crystal, the mol-ecules of the title compound, C(15)H(10)BrNO, are connected into centrosymmetric dimers by pairs of N-H⋯O hydrogen bonds. The dihedral angle between the planes of indole ring system and benzene ring is 50.13 (5)°. The indole plane is significantly less twisted from the plane of the central C-C(=O)-C bridge than the benzene plane [dihedral angles = 15.51 (3) and 40.13 (7)°, respectively]. The bond angles within the benzene ring show an approximately additive effect of the influence of both substituents.

Related literature

For applications of indoles, see: Murphy et al. (1997 ▶); Gupta et al. (1982 ▶); Al-Soud et al. (2004 ▶); Shigenaga et al. (1993 ▶); Butera et al. (2001 ▶). For synthethic procedures, see: Robinson (1982 ▶); Walsh et al. (1984 ▶). For related crystal structures of 7-pyridyl­indoles, see: Mudadu et al. (2006 ▶). For the influence of the substituent on the geometry of the phenyl ring, see: Domenicano (1988 ▶). For a description of the Cambridge Structural Database, see: Allen (2002 ▶).

Experimental

Crystal data

C15H10BrNO

M = 300.15

Monoclinic,

a = 11.3241 (4) Å

b = 7.4651 (3) Å

c = 14.9579 (5) Å

β = 103.100 (4)°

V = 1231.57 (8) Å3

Z = 4

Mo Kα radiation

μ = 3.32 mm−1

T = 291 K

0.4 × 0.2 × 0.15 mm

Data collection

Oxford Diffraction Xcalibur (Sapphire2, large Be window) diffractometer

Absorption correction: multi-scan (CrysAlis Pro; Oxford Diffraction, 2009 ▶) T min = 0.26, T max = 0.60

25357 measured reflections

2558 independent reflections

1864 reflections with I > 2σ(I)

R int = 0.036

Refinement

R[F 2 > 2σ(F 2)] = 0.024

wR(F 2) = 0.063

S = 1.06

2558 reflections

174 parameters

H-atom parameters constrained

Δρmax = 0.34 e Å−3

Δρmin = −0.29 e Å−3

Data collection: CrysAlis Pro (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis Pro; data reduction: CrysAlis Pro; program(s) used to solve structure: SIR92 (Altomare et al., 1993 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: Stereochemical Workstation Operation Manual (Siemens, 1989 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809040914/er2074sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809040914/er2074Isup2.hkl

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

C15H10BrNO	F(000) = 600
Mr = 300.15	Dx = 1.619 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 12183 reflections
a = 11.3241 (4) Å	θ = 2.0–26.8°
b = 7.4651 (3) Å	µ = 3.32 mm−1
c = 14.9579 (5) Å	T = 291 K
β = 103.100 (4)°	Block, colourless
V = 1231.57 (8) Å3	0.4 × 0.2 × 0.15 mm
Z = 4

Oxford Diffraction Xcalibur (Sapphire2, large Be window) diffractometer	2558 independent reflections
Radiation source: Enhance (Mo) X-ray Source	1864 reflections with I > 2σ(I)
graphite	Rint = 0.036
Detector resolution: 8.1929 pixels mm-1	θmax = 26.8°, θmin = 2.1°
ω scans	h = −13→14
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)	k = −9→9
Tmin = 0.26, Tmax = 0.60	l = −18→18
25357 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)] = 0.024	H-atom parameters constrained
wR(F2) = 0.063	w = 1/[σ2(Fo2) + (0.035P)2] where P = (Fo2 + 2Fc2)/3
S = 1.06	(Δ/σ)max = 0.001
2558 reflections	Δρmax = 0.34 e Å−3
174 parameters	Δρmin = −0.29 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0139 (9)

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	0.28642 (14)	−0.0239 (2)	0.94540 (10)	0.0386 (4)
H1	0.3601	−0.0274	0.9768	0.053 (6)*
C2	0.18656 (19)	−0.0579 (3)	0.97896 (14)	0.0459 (5)
H2	0.1876	−0.0872	1.0396	0.043 (5)*
C3	0.08506 (18)	−0.0424 (3)	0.91063 (14)	0.0449 (5)
H3	0.0056	−0.0604	0.9157	0.053 (6)*
C4	0.12356 (15)	0.0064 (3)	0.83002 (13)	0.0344 (4)
C5	0.25153 (15)	0.0167 (3)	0.85411 (11)	0.0315 (4)
C6	0.32088 (15)	0.0562 (2)	0.78996 (12)	0.0314 (4)
C7	0.25687 (16)	0.0912 (2)	0.70024 (12)	0.0353 (4)
H7	0.2995	0.1200	0.6559	0.035 (5)*
C8	0.13073 (17)	0.0839 (2)	0.67577 (13)	0.0400 (5)
H8	0.0908	0.1083	0.6155	0.046 (6)*
C9	0.06422 (17)	0.0413 (2)	0.73904 (14)	0.0387 (5)
H9	−0.0199	0.0357	0.7215	0.053 (6)*
C10	0.45391 (16)	0.0642 (2)	0.81808 (12)	0.0372 (4)
O10	0.50404 (12)	0.0723 (2)	0.90015 (9)	0.0593 (5)
C11	0.53044 (15)	0.0650 (2)	0.74900 (12)	0.0322 (4)
C12	0.50633 (16)	−0.0445 (2)	0.67135 (13)	0.0352 (4)
H12	0.4387	−0.1188	0.6605	0.041 (6)*
C13	0.58143 (17)	−0.0438 (2)	0.61058 (12)	0.0371 (5)
H13	0.5656	−0.1189	0.5596	0.035 (5)*
C14	0.68042 (16)	0.0694 (3)	0.62617 (12)	0.0363 (4)
Br14	0.779765 (18)	0.07710 (3)	0.539996 (14)	0.05633 (12)
C15	0.70737 (16)	0.1777 (3)	0.70285 (12)	0.0389 (5)
H15	0.7746	0.2529	0.7129	0.051 (6)*
C16	0.63296 (15)	0.1728 (3)	0.76455 (12)	0.0366 (4)
H16	0.6519	0.2428	0.8173	0.036 (5)*

	U11	U22	U33	U12	U13	U23
N1	0.0302 (9)	0.0511 (11)	0.0332 (8)	−0.0010 (8)	0.0045 (7)	0.0004 (7)
C2	0.0452 (12)	0.0568 (14)	0.0390 (10)	−0.0020 (10)	0.0167 (9)	−0.0002 (10)
C3	0.0309 (11)	0.0563 (14)	0.0504 (12)	−0.0031 (10)	0.0157 (9)	−0.0039 (10)
C4	0.0294 (10)	0.0291 (10)	0.0446 (10)	0.0011 (8)	0.0080 (8)	−0.0049 (9)
C5	0.0303 (10)	0.0275 (10)	0.0350 (10)	0.0002 (8)	0.0034 (7)	−0.0032 (8)
C6	0.0268 (9)	0.0303 (11)	0.0353 (9)	−0.0016 (8)	0.0032 (7)	−0.0017 (8)
C7	0.0326 (10)	0.0355 (11)	0.0367 (10)	−0.0008 (9)	0.0057 (8)	0.0033 (8)
C8	0.0348 (11)	0.0415 (12)	0.0387 (10)	0.0027 (9)	−0.0020 (8)	0.0028 (9)
C9	0.0248 (10)	0.0376 (12)	0.0502 (11)	0.0015 (8)	0.0011 (8)	−0.0024 (9)
C10	0.0320 (10)	0.0415 (12)	0.0358 (10)	−0.0035 (9)	0.0028 (8)	0.0037 (9)
O10	0.0339 (8)	0.1051 (14)	0.0347 (7)	−0.0108 (8)	−0.0010 (6)	0.0059 (8)
C11	0.0240 (9)	0.0341 (10)	0.0353 (9)	0.0015 (8)	−0.0004 (7)	0.0034 (8)
C12	0.0283 (10)	0.0321 (12)	0.0410 (10)	−0.0031 (8)	−0.0007 (8)	0.0021 (8)
C13	0.0354 (11)	0.0350 (12)	0.0363 (10)	0.0059 (9)	−0.0015 (8)	−0.0007 (9)
C14	0.0283 (10)	0.0428 (12)	0.0366 (9)	0.0071 (9)	0.0047 (8)	0.0086 (9)
Br14	0.04658 (16)	0.0801 (2)	0.04560 (15)	0.00255 (12)	0.01738 (10)	0.00603 (11)
C15	0.0268 (10)	0.0424 (12)	0.0454 (11)	−0.0057 (9)	0.0034 (8)	−0.0012 (9)
C16	0.0284 (10)	0.0402 (12)	0.0386 (10)	−0.0011 (9)	0.0020 (8)	−0.0045 (9)

N1—C2	1.361 (3)	C8—H8	0.9300
N1—C5	1.367 (2)	C9—H9	0.9300
N1—H1	0.8600	C10—O10	1.232 (2)
C2—C3	1.359 (3)	C10—C11	1.492 (2)
C2—H2	0.9300	C11—C16	1.388 (2)
C3—C4	1.419 (3)	C11—C12	1.395 (3)
C3—H3	0.9300	C12—C13	1.378 (3)
C4—C9	1.399 (3)	C12—H12	0.9300
C4—C5	1.414 (2)	C13—C14	1.381 (3)
C5—C6	1.402 (2)	C13—H13	0.9300
C6—C7	1.398 (2)	C14—C15	1.380 (3)
C6—C10	1.471 (2)	C14—Br14	1.8941 (18)
C7—C8	1.393 (2)	C15—C16	1.384 (2)
C7—H7	0.9300	C15—H15	0.9300
C8—C9	1.374 (3)	C16—H16	0.9300
C2—N1—C5	109.49 (16)	C8—C9—C4	119.72 (17)
C2—N1—H1	125.3	C8—C9—H9	120.1
C5—N1—H1	125.3	C4—C9—H9	120.1
C3—C2—N1	109.79 (18)	O10—C10—C6	119.87 (17)
C3—C2—H2	125.1	O10—C10—C11	118.77 (17)
N1—C2—H2	125.1	C6—C10—C11	121.36 (15)
C2—C3—C4	106.88 (17)	C16—C11—C12	118.51 (17)
C2—C3—H3	126.6	C16—C11—C10	118.77 (16)
C4—C3—H3	126.6	C12—C11—C10	122.66 (16)
C9—C4—C5	118.45 (17)	C13—C12—C11	120.89 (17)
C9—C4—C3	134.58 (18)	C13—C12—H12	119.6
C5—C4—C3	106.97 (16)	C11—C12—H12	119.6
N1—C5—C6	130.57 (15)	C12—C13—C14	119.29 (17)
N1—C5—C4	106.86 (16)	C12—C13—H13	120.4
C6—C5—C4	122.53 (15)	C14—C13—H13	120.4
C7—C6—C5	116.57 (16)	C15—C14—C13	121.14 (17)
C7—C6—C10	122.80 (16)	C15—C14—Br14	119.62 (14)
C5—C6—C10	120.61 (15)	C13—C14—Br14	119.24 (14)
C8—C7—C6	121.52 (17)	C14—C15—C16	119.04 (18)
C8—C7—H7	119.2	C14—C15—H15	120.5
C6—C7—H7	119.2	C16—C15—H15	120.5
C9—C8—C7	121.18 (17)	C15—C16—C11	121.07 (18)
C9—C8—H8	119.4	C15—C16—H16	119.5
C7—C8—H8	119.4	C11—C16—H16	119.5
C5—N1—C2—C3	0.7 (2)	C3—C4—C9—C8	−179.0 (2)
N1—C2—C3—C4	−0.8 (2)	C7—C6—C10—O10	163.69 (18)
C2—C3—C4—C9	179.9 (2)	C5—C6—C10—O10	−14.7 (3)
C2—C3—C4—C5	0.6 (2)	C7—C6—C10—C11	−15.5 (3)
C2—N1—C5—C6	−178.08 (19)	C5—C6—C10—C11	166.12 (17)
C2—N1—C5—C4	−0.3 (2)	O10—C10—C11—C16	−37.9 (3)
C9—C4—C5—N1	−179.61 (17)	C6—C10—C11—C16	141.34 (18)
C3—C4—C5—N1	−0.2 (2)	O10—C10—C11—C12	139.08 (19)
C9—C4—C5—C6	−1.6 (3)	C6—C10—C11—C12	−41.7 (3)
C3—C4—C5—C6	177.79 (17)	C16—C11—C12—C13	−1.0 (3)
N1—C5—C6—C7	179.52 (18)	C10—C11—C12—C13	−177.97 (16)
C4—C5—C6—C7	2.0 (3)	C11—C12—C13—C14	−1.2 (3)
N1—C5—C6—C10	−2.0 (3)	C12—C13—C14—C15	2.0 (3)
C4—C5—C6—C10	−179.52 (18)	C12—C13—C14—Br14	−177.47 (13)
C5—C6—C7—C8	−1.1 (3)	C13—C14—C15—C16	−0.4 (3)
C10—C6—C7—C8	−179.52 (17)	Br14—C14—C15—C16	179.00 (14)
C6—C7—C8—C9	−0.2 (3)	C14—C15—C16—C11	−1.9 (3)
C7—C8—C9—C4	0.7 (3)	C12—C11—C16—C15	2.5 (3)
C5—C4—C9—C8	0.2 (3)	C10—C11—C16—C15	179.66 (17)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O10i	0.86	2.14	2.935 (2)	153

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O10i	0.86	2.14	2.935 (2)	153

Symmetry code: (i) .