5-Chloro-3-[(E)-1,2-diphenyl-ethen-yl]-1H-indole.

In the title compound, C(22)H(16)ClN, the pyrrole system makes a dihedral angle of 68.9 (1)° with the plane of phenyl ring at the ethenyl 1-position. An intra-molecular C-H⋯π inter-action is observed. In the crystal, inter-molecular C-H⋯π inter-actions link the mol-ecules into infinite chains running along the b axis.

Related literature

For the synthesis and potential uses of indole derivatives, see: Bhuvaneswari et al. (2007 ▶); Ghosh & Maiti (2007 ▶); Sakai et al. (2008 ▶); Kakiuchi & Kochi (2008 ▶). For the general synthetic procedure and structure analysis of a derivative of the title compound, see: Bhaskar et al. (2010 ▶). For standard bond lengths, see Allen et al. (1987 ▶).

Experimental

Crystal data

C22H16ClN

M = 329.81

Monoclinic,

a = 10.8869 (6) Å

b = 14.0373 (8) Å

c = 10.7978 (4) Å

β = 91.706 (2)°

V = 1649.42 (14) Å3

Z = 4

Mo Kα radiation

μ = 0.23 mm−1

T = 298 K

0.35 × 0.22 × 0.20 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2004 ▶) T min = 0.923, T max = 0.955

12914 measured reflections

3928 independent reflections

2804 reflections with I > 2σ(I)

R int = 0.023

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.108

S = 1.32

3928 reflections

221 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.24 e Å−3

Δρmin = −0.23 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: APEX2 and SAINT (Bruker, 2004 ▶); data reduction: SAINT and XPREP (Bruker, 2004 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810034719/im2219sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810034719/im2219Isup2.hkl

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

C22H16ClN	F(000) = 688
Mr = 329.81	Dx = 1.328 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3737 reflections
a = 10.8869 (6) Å	θ = 2.4–27.7°
b = 14.0373 (8) Å	µ = 0.23 mm−1
c = 10.7978 (4) Å	T = 298 K
β = 91.706 (2)°	Block, colourless
V = 1649.42 (14) Å3	0.35 × 0.22 × 0.20 mm
Z = 4

Bruker Kappa APEXII CCD diffractometer	3928 independent reflections
Radiation source: fine-focus sealed tube	2804 reflections with I > 2σ(I)
graphite	Rint = 0.023
ω and φ scan	θmax = 28.3°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −14→10
Tmin = 0.923, Tmax = 0.955	k = −18→18
12914 measured reflections	l = −14→10

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.108	H atoms treated by a mixture of independent and constrained refinement
S = 1.32	w = 1/[σ2(Fo2) + (0.0422P)2] where P = (Fo2 + 2Fc2)/3
3928 reflections	(Δ/σ)max = 0.001
221 parameters	Δρmax = 0.24 e Å−3
0 restraints	Δρmin = −0.23 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
C1	0.50474 (15)	0.38298 (11)	0.55429 (14)	0.0442 (4)
H1	0.4308	0.4161	0.5542	0.053*
C2	0.52390 (13)	0.29966 (10)	0.49125 (12)	0.0353 (3)
C3	0.65154 (13)	0.27519 (10)	0.51474 (12)	0.0339 (3)
C4	0.72997 (13)	0.20455 (10)	0.47216 (13)	0.0381 (3)
H4	0.7013	0.1582	0.4169	0.046*
C5	0.85081 (13)	0.20491 (11)	0.51365 (13)	0.0417 (4)
C6	0.89718 (14)	0.27230 (12)	0.59749 (14)	0.0493 (4)
H6	0.9785	0.2686	0.6261	0.059*
C7	0.82271 (15)	0.34403 (12)	0.63776 (14)	0.0494 (4)
H7	0.8528	0.3903	0.6923	0.059*
C8	0.70140 (14)	0.34575 (11)	0.59495 (13)	0.0398 (4)
C9	0.43048 (12)	0.24722 (10)	0.41772 (12)	0.0353 (3)
C10	0.32774 (13)	0.30607 (10)	0.36239 (13)	0.0353 (3)
C11	0.22693 (15)	0.32999 (12)	0.42986 (14)	0.0508 (4)
H11	0.2238	0.3121	0.5127	0.061*
C12	0.13000 (16)	0.38050 (12)	0.37533 (16)	0.0580 (5)
H12	0.0624	0.3964	0.4217	0.070*
C13	0.13352 (15)	0.40699 (12)	0.25378 (16)	0.0524 (4)
H13	0.0676	0.4397	0.2171	0.063*
C14	0.23442 (15)	0.38539 (11)	0.18569 (15)	0.0502 (4)
H14	0.2377	0.4046	0.1034	0.060*
C15	0.33150 (13)	0.33484 (11)	0.23991 (13)	0.0417 (4)
H15	0.3996	0.3202	0.1936	0.050*
C16	0.43655 (13)	0.15227 (11)	0.40398 (12)	0.0393 (3)
H16	0.5036	0.1243	0.4451	0.047*
C17	0.35713 (13)	0.08460 (10)	0.33620 (12)	0.0358 (3)
C18	0.23999 (14)	0.10354 (11)	0.28396 (15)	0.0467 (4)
H18	0.2056	0.1637	0.2930	0.056*
C19	0.17550 (15)	0.03436 (12)	0.21967 (15)	0.0532 (4)
H19	0.0985	0.0488	0.1851	0.064*
C20	0.22244 (15)	−0.05556 (13)	0.20551 (15)	0.0524 (4)
H20	0.1780	−0.1015	0.1612	0.063*
C21	0.33554 (16)	−0.07694 (12)	0.25734 (14)	0.0494 (4)
H21	0.3679	−0.1378	0.2491	0.059*
C22	0.40145 (14)	−0.00790 (11)	0.32190 (13)	0.0425 (4)
H22	0.4778	−0.0236	0.3570	0.051*
Cl1	0.95028 (4)	0.11701 (3)	0.46169 (4)	0.06518 (18)
N1	0.60946 (13)	0.41032 (10)	0.61706 (13)	0.0498 (4)
H1N	0.6191 (16)	0.4607 (14)	0.6598 (16)	0.070 (6)*

	U11	U22	U33	U12	U13	U23
C1	0.0442 (9)	0.0412 (9)	0.0470 (9)	0.0070 (7)	0.0014 (7)	−0.0023 (7)
C2	0.0394 (8)	0.0331 (8)	0.0335 (8)	0.0034 (6)	0.0016 (6)	0.0022 (6)
C3	0.0386 (8)	0.0327 (7)	0.0303 (7)	−0.0002 (6)	−0.0013 (6)	0.0011 (6)
C4	0.0404 (8)	0.0362 (8)	0.0374 (8)	0.0014 (6)	−0.0048 (6)	−0.0033 (6)
C5	0.0386 (8)	0.0430 (9)	0.0431 (9)	0.0072 (7)	−0.0028 (6)	−0.0003 (7)
C6	0.0415 (9)	0.0549 (10)	0.0506 (9)	−0.0018 (8)	−0.0122 (7)	−0.0020 (8)
C7	0.0532 (10)	0.0476 (9)	0.0468 (9)	−0.0069 (8)	−0.0106 (7)	−0.0097 (8)
C8	0.0463 (9)	0.0365 (8)	0.0365 (8)	0.0006 (7)	−0.0013 (7)	−0.0024 (6)
C9	0.0328 (7)	0.0362 (8)	0.0368 (8)	0.0045 (6)	0.0015 (6)	0.0011 (6)
C10	0.0348 (7)	0.0313 (7)	0.0396 (8)	0.0016 (6)	−0.0016 (6)	−0.0022 (6)
C11	0.0505 (10)	0.0595 (11)	0.0427 (9)	0.0174 (8)	0.0055 (7)	0.0036 (8)
C12	0.0458 (10)	0.0673 (12)	0.0613 (12)	0.0218 (9)	0.0066 (8)	−0.0043 (9)
C13	0.0469 (10)	0.0491 (10)	0.0604 (11)	0.0137 (8)	−0.0133 (8)	−0.0027 (8)
C14	0.0548 (10)	0.0509 (10)	0.0442 (9)	0.0024 (8)	−0.0096 (8)	0.0077 (7)
C15	0.0376 (8)	0.0445 (9)	0.0431 (9)	−0.0006 (7)	0.0023 (7)	0.0012 (7)
C16	0.0365 (8)	0.0395 (8)	0.0417 (8)	0.0057 (7)	−0.0051 (6)	0.0043 (7)
C17	0.0374 (8)	0.0351 (8)	0.0351 (8)	−0.0011 (6)	0.0040 (6)	0.0035 (6)
C18	0.0363 (8)	0.0399 (9)	0.0637 (10)	0.0012 (7)	−0.0003 (7)	−0.0007 (7)
C19	0.0377 (9)	0.0542 (11)	0.0673 (11)	−0.0060 (8)	−0.0053 (8)	−0.0009 (9)
C20	0.0521 (10)	0.0496 (10)	0.0556 (10)	−0.0110 (8)	0.0011 (8)	−0.0076 (8)
C21	0.0581 (10)	0.0382 (9)	0.0522 (10)	0.0015 (8)	0.0045 (8)	−0.0049 (7)
C22	0.0444 (9)	0.0399 (9)	0.0430 (8)	0.0046 (7)	0.0010 (7)	0.0031 (7)
Cl1	0.0498 (3)	0.0732 (3)	0.0715 (3)	0.0262 (2)	−0.0158 (2)	−0.0199 (2)
N1	0.0554 (9)	0.0405 (8)	0.0536 (8)	0.0029 (7)	−0.0008 (7)	−0.0156 (7)

C1—N1	1.364 (2)	C12—C13	1.366 (2)
C1—C2	1.3723 (19)	C12—H12	0.9300
C1—H1	0.9300	C13—C14	1.374 (2)
C2—C3	1.4464 (19)	C13—H13	0.9300
C2—C9	1.4692 (19)	C14—C15	1.388 (2)
C3—C4	1.3955 (19)	C14—H14	0.9300
C3—C8	1.4134 (19)	C15—H15	0.9300
C4—C5	1.3770 (19)	C16—C17	1.4655 (19)
C4—H4	0.9300	C16—H16	0.9300
C5—C6	1.394 (2)	C17—C22	1.3954 (19)
C5—Cl1	1.7454 (15)	C17—C18	1.4044 (19)
C6—C7	1.371 (2)	C18—C19	1.374 (2)
C6—H6	0.9300	C18—H18	0.9300
C7—C8	1.386 (2)	C19—C20	1.372 (2)
C7—H7	0.9300	C19—H19	0.9300
C8—N1	1.376 (2)	C20—C21	1.371 (2)
C9—C16	1.343 (2)	C20—H20	0.9300
C9—C10	1.5003 (18)	C21—C22	1.382 (2)
C10—C11	1.3768 (19)	C21—H21	0.9300
C10—C15	1.3845 (19)	C22—H22	0.9300
C11—C12	1.388 (2)	N1—H1N	0.849 (19)
C11—H11	0.9300
N1—C1—C2	110.43 (14)	C11—C12—H12	119.9
N1—C1—H1	124.8	C12—C13—C14	119.99 (15)
C2—C1—H1	124.8	C12—C13—H13	120.0
C1—C2—C3	105.95 (13)	C14—C13—H13	120.0
C1—C2—C9	125.59 (13)	C13—C14—C15	119.88 (15)
C3—C2—C9	128.44 (12)	C13—C14—H14	120.1
C4—C3—C8	118.18 (13)	C15—C14—H14	120.1
C4—C3—C2	134.83 (12)	C10—C15—C14	120.54 (14)
C8—C3—C2	106.89 (12)	C10—C15—H15	119.7
C5—C4—C3	118.57 (13)	C14—C15—H15	119.7
C5—C4—H4	120.7	C9—C16—C17	131.93 (13)
C3—C4—H4	120.7	C9—C16—H16	114.0
C4—C5—C6	122.54 (14)	C17—C16—H16	114.0
C4—C5—Cl1	119.25 (11)	C22—C17—C18	116.39 (13)
C6—C5—Cl1	118.20 (12)	C22—C17—C16	117.23 (13)
C7—C6—C5	119.88 (14)	C18—C17—C16	126.38 (13)
C7—C6—H6	120.1	C19—C18—C17	120.89 (15)
C5—C6—H6	120.1	C19—C18—H18	119.6
C6—C7—C8	118.25 (14)	C17—C18—H18	119.6
C6—C7—H7	120.9	C20—C19—C18	121.33 (15)
C8—C7—H7	120.9	C20—C19—H19	119.3
N1—C8—C7	130.09 (14)	C18—C19—H19	119.3
N1—C8—C3	107.44 (13)	C21—C20—C19	119.28 (15)
C7—C8—C3	122.46 (14)	C21—C20—H20	120.4
C16—C9—C2	121.43 (13)	C19—C20—H20	120.4
C16—C9—C10	122.76 (13)	C20—C21—C22	119.93 (15)
C2—C9—C10	115.80 (12)	C20—C21—H21	120.0
C11—C10—C15	118.76 (13)	C22—C21—H21	120.0
C11—C10—C9	121.34 (13)	C21—C22—C17	122.16 (14)
C15—C10—C9	119.87 (12)	C21—C22—H22	118.9
C10—C11—C12	120.53 (15)	C17—C22—H22	118.9
C10—C11—H11	119.7	C1—N1—C8	109.26 (13)
C12—C11—H11	119.7	C1—N1—H1N	126.3 (12)
C13—C12—C11	120.27 (15)	C8—N1—H1N	124.3 (12)
C13—C12—H12	119.9
N1—C1—C2—C3	−1.52 (17)	C16—C9—C10—C15	−83.04 (18)
N1—C1—C2—C9	177.44 (13)	C2—C9—C10—C15	98.36 (15)
C1—C2—C3—C4	−174.63 (16)	C15—C10—C11—C12	1.1 (2)
C9—C2—C3—C4	6.5 (3)	C9—C10—C11—C12	−176.83 (15)
C1—C2—C3—C8	1.51 (16)	C10—C11—C12—C13	0.1 (3)
C9—C2—C3—C8	−177.41 (13)	C11—C12—C13—C14	−1.4 (3)
C8—C3—C4—C5	2.3 (2)	C12—C13—C14—C15	1.4 (3)
C2—C3—C4—C5	178.11 (15)	C11—C10—C15—C14	−1.1 (2)
C3—C4—C5—C6	0.8 (2)	C9—C10—C15—C14	176.88 (14)
C3—C4—C5—Cl1	179.88 (11)	C13—C14—C15—C10	−0.1 (2)
C4—C5—C6—C7	−2.7 (2)	C2—C9—C16—C17	−179.56 (14)
Cl1—C5—C6—C7	178.18 (12)	C10—C9—C16—C17	1.9 (2)
C5—C6—C7—C8	1.4 (2)	C9—C16—C17—C22	168.54 (15)
C6—C7—C8—N1	−177.70 (16)	C9—C16—C17—C18	−11.6 (3)
C6—C7—C8—C3	1.8 (2)	C22—C17—C18—C19	−1.7 (2)
C4—C3—C8—N1	175.92 (12)	C16—C17—C18—C19	178.39 (14)
C2—C3—C8—N1	−0.98 (16)	C17—C18—C19—C20	0.8 (3)
C4—C3—C8—C7	−3.7 (2)	C18—C19—C20—C21	0.5 (3)
C2—C3—C8—C7	179.42 (14)	C19—C20—C21—C22	−0.7 (2)
C1—C2—C9—C16	−150.83 (15)	C20—C21—C22—C17	−0.4 (2)
C3—C2—C9—C16	27.9 (2)	C18—C17—C22—C21	1.5 (2)
C1—C2—C9—C10	27.8 (2)	C16—C17—C22—C21	−178.55 (14)
C3—C2—C9—C10	−153.48 (13)	C2—C1—N1—C8	0.95 (18)
C16—C9—C10—C11	94.92 (18)	C7—C8—N1—C1	179.63 (16)
C2—C9—C10—C11	−83.68 (17)	C3—C8—N1—C1	0.06 (18)

Cg1and Cg2 are the centroids of the C10–C15 and C3–C8 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C18—H18···Cg1	0.93	2.74	3.573 (2)	150
C20—H20···Cg2i	0.93	2.97	3.690 (2)	136

Table 1

Hydrogen-bond geometry (Å, °)

Cg1and Cg2 are the centroids of the C10–C15 and C3–C8 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C18—H18⋯Cg1	0.93	2.74	3.573 (2)	150
C20—H20⋯Cg2i	0.93	2.97	3.690 (2)	136

Symmetry code: (i) .