2-Benzyl-6-chloro-1-(4-methyl-phen-yl)-1H-indole-3-carbonitrile.

In the title compound, C(23)H(17)ClN(2), the dihedral angle between the indole ring and the attached tolyl ring is 86.97 (8)°. Weak C-H⋯N(nitrile) hydrogen bonding, and C-H⋯π(aromatic) and short Cl⋯π(aromatic) [3.628 (1) Å] inter-actions consolidate the crystal packing.

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 ▶,c ▶). For standard bond lengths, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C23H17ClN2

M = 356.84

Monoclinic,

a = 10.0003 (10) Å

b = 9.8565 (8) Å

c = 18.539 (2) Å

β = 93.926 (9)°

V = 1823.1 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.22 mm−1

T = 113 K

0.20 × 0.16 × 0.10 mm

Data collection

Rigaku Saturn724 CCD diffractometer

Absorption correction: multi-scan (CrystalClear-SM Expert; Rigaku, 2009 ▶) T min = 0.958, T max = 0.979

18792 measured reflections

4382 independent reflections

1947 reflections with I > 2σ(I)

R int = 0.079

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.103

S = 0.85

4382 reflections

237 parameters

H-atom parameters constrained

Δρmax = 0.35 e Å−3

Δρmin = −0.30 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: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811048422/zl2420sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811048422/zl2420Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811048422/zl2420Isup3.cml

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

C23H17ClN2	F(000) = 744
Mr = 356.84	Dx = 1.300 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 6077 reflections
a = 10.0003 (10) Å	θ = 2.0–28.0°
b = 9.8565 (8) Å	µ = 0.22 mm−1
c = 18.539 (2) Å	T = 113 K
β = 93.926 (9)°	Prism, colorless
V = 1823.1 (3) Å3	0.20 × 0.16 × 0.10 mm
Z = 4

Rigaku Saturn724 CCD diffractometer	4382 independent reflections
Radiation source: rotating anode	1947 reflections with I > 2σ(I)
multilayer	Rint = 0.079
Detector resolution: 14.22 pixels mm-1	θmax = 28.0°, θmin = 2.0°
ω and φ scans	h = −12→13
Absorption correction: multi-scan (CrystalClear-SM Expert; Rigaku, 2009)	k = −12→12
Tmin = 0.958, Tmax = 0.979	l = −24→24
18792 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)] = 0.041	H-atom parameters constrained
wR(F2) = 0.103	w = 1/[σ2(Fo2) + (0.0361P)2] where P = (Fo2 + 2Fc2)/3
S = 0.85	(Δ/σ)max < 0.001
4382 reflections	Δρmax = 0.35 e Å−3
237 parameters	Δρmin = −0.30 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: 0.0033 (5)

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
Cl1	−0.03716 (5)	1.21324 (5)	0.09402 (3)	0.03050 (16)
N1	0.12552 (15)	0.71133 (16)	0.10904 (7)	0.0212 (4)
N2	0.54914 (18)	0.70088 (18)	0.00901 (9)	0.0377 (5)
C1	0.13022 (19)	0.84896 (19)	0.09184 (9)	0.0212 (4)
C2	0.0363 (2)	0.94986 (19)	0.10034 (9)	0.0231 (5)
H2	−0.0485	0.9312	0.1184	0.028*
C3	0.0728 (2)	1.0788 (2)	0.08114 (9)	0.0238 (5)
C4	0.19515 (19)	1.1085 (2)	0.05278 (9)	0.0260 (5)
H4	0.2159	1.1992	0.0403	0.031*
C5	0.2855 (2)	1.0062 (2)	0.04304 (10)	0.0251 (5)
H5	0.3684	1.0253	0.0230	0.030*
C6	0.25444 (19)	0.8741 (2)	0.06279 (9)	0.0216 (4)
C7	0.32207 (19)	0.7456 (2)	0.06210 (9)	0.0230 (5)
C8	0.24230 (19)	0.6490 (2)	0.09126 (9)	0.0236 (5)
C9	0.27113 (19)	0.50407 (19)	0.10918 (10)	0.0252 (5)
H9A	0.3431	0.4712	0.0795	0.030*
H9B	0.1899	0.4493	0.0966	0.030*
C10	0.31403 (19)	0.4831 (2)	0.18884 (10)	0.0235 (5)
C11	0.4009 (2)	0.5740 (2)	0.22559 (11)	0.0303 (5)
H11	0.4327	0.6509	0.2010	0.036*
C12	0.4411 (2)	0.5531 (2)	0.29759 (11)	0.0371 (6)
H12	0.5007	0.6154	0.3221	0.044*
C13	0.3951 (2)	0.4425 (2)	0.33395 (11)	0.0387 (6)
H13	0.4223	0.4290	0.3835	0.046*
C14	0.3092 (2)	0.3513 (2)	0.29807 (11)	0.0397 (6)
H14	0.2778	0.2746	0.3229	0.048*
C15	0.2687 (2)	0.3716 (2)	0.22582 (11)	0.0344 (5)
H15	0.2095	0.3087	0.2015	0.041*
C16	0.4488 (2)	0.7192 (2)	0.03379 (10)	0.0268 (5)
C17	0.00947 (19)	0.6386 (2)	0.12952 (9)	0.0220 (4)
C18	−0.0077 (2)	0.6062 (2)	0.20068 (10)	0.0328 (5)
H18	0.0541	0.6378	0.2381	0.039*
C19	−0.1160 (2)	0.5272 (2)	0.21686 (11)	0.0384 (6)
H19	−0.1279	0.5051	0.2659	0.046*
C20	−0.2076 (2)	0.4795 (2)	0.16341 (11)	0.0290 (5)
C21	−0.1911 (2)	0.5178 (2)	0.09294 (10)	0.0286 (5)
H21	−0.2551	0.4898	0.0557	0.034*
C22	−0.0833 (2)	0.59617 (19)	0.07563 (10)	0.0249 (5)
H22	−0.0730	0.6208	0.0268	0.030*
C23	−0.3186 (2)	0.3845 (2)	0.18130 (12)	0.0472 (7)
H23A	−0.3989	0.4038	0.1496	0.071*
H23B	−0.3389	0.3974	0.2318	0.071*
H23C	−0.2904	0.2906	0.1741	0.071*

	U11	U22	U33	U12	U13	U23
Cl1	0.0339 (3)	0.0245 (3)	0.0329 (3)	0.0083 (3)	0.0016 (2)	0.0004 (2)
N1	0.0207 (9)	0.0196 (9)	0.0233 (8)	0.0016 (8)	0.0017 (7)	−0.0009 (7)
N2	0.0329 (11)	0.0306 (11)	0.0507 (12)	0.0012 (10)	0.0121 (9)	−0.0055 (9)
C1	0.0258 (11)	0.0186 (10)	0.0186 (9)	−0.0005 (10)	−0.0025 (8)	−0.0004 (8)
C2	0.0237 (11)	0.0250 (11)	0.0201 (10)	0.0017 (9)	−0.0013 (8)	−0.0017 (9)
C3	0.0273 (12)	0.0218 (11)	0.0218 (10)	0.0062 (10)	−0.0027 (8)	−0.0017 (8)
C4	0.0303 (12)	0.0212 (11)	0.0259 (10)	0.0000 (10)	−0.0011 (9)	0.0008 (9)
C5	0.0251 (12)	0.0255 (12)	0.0248 (10)	−0.0005 (10)	0.0014 (8)	−0.0002 (9)
C6	0.0227 (11)	0.0211 (11)	0.0205 (10)	0.0016 (9)	−0.0016 (8)	−0.0009 (8)
C7	0.0214 (11)	0.0232 (12)	0.0245 (10)	0.0023 (9)	0.0014 (8)	−0.0032 (8)
C8	0.0266 (12)	0.0221 (11)	0.0217 (9)	0.0052 (10)	−0.0012 (8)	−0.0053 (9)
C9	0.0249 (12)	0.0218 (11)	0.0287 (11)	0.0001 (10)	0.0004 (9)	−0.0045 (9)
C10	0.0198 (11)	0.0211 (11)	0.0297 (11)	0.0053 (9)	0.0020 (8)	−0.0014 (9)
C11	0.0317 (13)	0.0227 (12)	0.0360 (12)	0.0037 (10)	−0.0008 (10)	0.0023 (9)
C12	0.0389 (14)	0.0317 (13)	0.0387 (13)	0.0050 (11)	−0.0107 (10)	−0.0059 (11)
C13	0.0474 (15)	0.0377 (14)	0.0303 (12)	0.0129 (12)	−0.0036 (11)	0.0014 (10)
C14	0.0456 (15)	0.0351 (14)	0.0387 (13)	0.0022 (13)	0.0044 (11)	0.0105 (11)
C15	0.0350 (13)	0.0285 (13)	0.0394 (12)	−0.0016 (11)	0.0005 (10)	0.0007 (10)
C16	0.0317 (13)	0.0177 (11)	0.0310 (11)	0.0018 (10)	0.0011 (9)	−0.0025 (9)
C17	0.0230 (11)	0.0197 (11)	0.0234 (10)	0.0043 (9)	0.0023 (8)	0.0028 (8)
C18	0.0313 (13)	0.0446 (14)	0.0222 (11)	0.0006 (11)	−0.0016 (9)	−0.0002 (10)
C19	0.0360 (14)	0.0543 (16)	0.0259 (11)	0.0043 (13)	0.0097 (10)	0.0115 (11)
C20	0.0264 (12)	0.0227 (12)	0.0387 (12)	0.0083 (10)	0.0092 (10)	0.0043 (10)
C21	0.0289 (12)	0.0266 (12)	0.0300 (11)	0.0008 (10)	0.0004 (9)	−0.0045 (9)
C22	0.0304 (12)	0.0239 (11)	0.0207 (10)	0.0009 (10)	0.0032 (8)	0.0006 (9)
C23	0.0372 (15)	0.0389 (15)	0.0681 (17)	0.0018 (13)	0.0230 (12)	0.0092 (13)

Cl1—C3	1.7487 (19)	C11—C12	1.383 (3)
N1—C8	1.379 (2)	C11—H11	0.9500
N1—C1	1.395 (2)	C12—C13	1.377 (3)
N1—C17	1.437 (2)	C12—H12	0.9500
N2—C16	1.146 (2)	C13—C14	1.382 (3)
C1—C2	1.385 (2)	C13—H13	0.9500
C1—C6	1.409 (2)	C14—C15	1.387 (3)
C2—C3	1.375 (2)	C14—H14	0.9500
C2—H2	0.9500	C15—H15	0.9500
C3—C4	1.396 (3)	C17—C18	1.379 (2)
C4—C5	1.374 (2)	C17—C22	1.381 (2)
C4—H4	0.9500	C18—C19	1.384 (3)
C5—C6	1.393 (3)	C18—H18	0.9500
C5—H5	0.9500	C19—C20	1.385 (3)
C6—C7	1.436 (3)	C19—H19	0.9500
C7—C8	1.376 (3)	C20—C21	1.381 (3)
C7—C16	1.428 (3)	C20—C23	1.506 (3)
C8—C9	1.490 (3)	C21—C22	1.382 (3)
C9—C10	1.523 (2)	C21—H21	0.9500
C9—H9A	0.9900	C22—H22	0.9500
C9—H9B	0.9900	C23—H23A	0.9800
C10—C15	1.387 (3)	C23—H23B	0.9800
C10—C11	1.393 (3)	C23—H23C	0.9800
C8—N1—C1	109.63 (16)	C10—C11—H11	119.8
C8—N1—C17	123.60 (16)	C13—C12—C11	120.4 (2)
C1—N1—C17	125.86 (16)	C13—C12—H12	119.8
C2—C1—N1	129.70 (18)	C11—C12—H12	119.8
C2—C1—C6	122.68 (18)	C12—C13—C14	119.8 (2)
N1—C1—C6	107.61 (17)	C12—C13—H13	120.1
C3—C2—C1	116.10 (18)	C14—C13—H13	120.1
C3—C2—H2	121.9	C13—C14—C15	120.1 (2)
C1—C2—H2	121.9	C13—C14—H14	119.9
C2—C3—C4	123.12 (19)	C15—C14—H14	119.9
C2—C3—Cl1	118.98 (16)	C14—C15—C10	120.5 (2)
C4—C3—Cl1	117.89 (15)	C14—C15—H15	119.7
C5—C4—C3	119.79 (19)	C10—C15—H15	119.7
C5—C4—H4	120.1	N2—C16—C7	177.6 (2)
C3—C4—H4	120.1	C18—C17—C22	120.01 (19)
C4—C5—C6	119.39 (19)	C18—C17—N1	121.59 (17)
C4—C5—H5	120.3	C22—C17—N1	118.34 (16)
C6—C5—H5	120.3	C17—C18—C19	119.23 (19)
C5—C6—C1	118.87 (18)	C17—C18—H18	120.4
C5—C6—C7	135.07 (18)	C19—C18—H18	120.4
C1—C6—C7	106.05 (17)	C18—C19—C20	121.69 (19)
C8—C7—C16	124.79 (18)	C18—C19—H19	119.2
C8—C7—C6	108.70 (16)	C20—C19—H19	119.2
C16—C7—C6	126.47 (18)	C21—C20—C19	117.9 (2)
C7—C8—N1	107.99 (17)	C21—C20—C23	121.1 (2)
C7—C8—C9	129.96 (18)	C19—C20—C23	120.98 (19)
N1—C8—C9	121.84 (18)	C20—C21—C22	121.22 (19)
C8—C9—C10	112.56 (15)	C20—C21—H21	119.4
C8—C9—H9A	109.1	C22—C21—H21	119.4
C10—C9—H9A	109.1	C17—C22—C21	119.84 (18)
C8—C9—H9B	109.1	C17—C22—H22	120.1
C10—C9—H9B	109.1	C21—C22—H22	120.1
H9A—C9—H9B	107.8	C20—C23—H23A	109.5
C15—C10—C11	118.79 (19)	C20—C23—H23B	109.5
C15—C10—C9	120.45 (18)	H23A—C23—H23B	109.5
C11—C10—C9	120.75 (18)	C20—C23—H23C	109.5
C12—C11—C10	120.42 (19)	H23A—C23—H23C	109.5
C12—C11—H11	119.8	H23B—C23—H23C	109.5
C8—N1—C1—C2	−179.86 (18)	C17—N1—C8—C9	−15.6 (3)
C17—N1—C1—C2	10.8 (3)	C7—C8—C9—C10	97.8 (2)
C8—N1—C1—C6	−0.43 (19)	N1—C8—C9—C10	−76.2 (2)
C17—N1—C1—C6	−169.82 (15)	C8—C9—C10—C15	140.01 (19)
N1—C1—C2—C3	177.05 (17)	C8—C9—C10—C11	−40.9 (2)
C6—C1—C2—C3	−2.3 (3)	C15—C10—C11—C12	0.1 (3)
C1—C2—C3—C4	1.7 (3)	C9—C10—C11—C12	−178.96 (17)
C1—C2—C3—Cl1	−177.16 (13)	C10—C11—C12—C13	−0.4 (3)
C2—C3—C4—C5	−0.1 (3)	C11—C12—C13—C14	0.6 (3)
Cl1—C3—C4—C5	178.81 (14)	C12—C13—C14—C15	−0.4 (3)
C3—C4—C5—C6	−1.0 (3)	C13—C14—C15—C10	0.1 (3)
C4—C5—C6—C1	0.5 (3)	C11—C10—C15—C14	0.0 (3)
C4—C5—C6—C7	−178.58 (19)	C9—C10—C15—C14	179.10 (18)
C2—C1—C6—C5	1.3 (3)	C8—N1—C17—C18	89.9 (2)
N1—C1—C6—C5	−178.18 (15)	C1—N1—C17—C18	−102.1 (2)
C2—C1—C6—C7	−179.42 (16)	C8—N1—C17—C22	−87.5 (2)
N1—C1—C6—C7	1.11 (19)	C1—N1—C17—C22	80.5 (2)
C5—C6—C7—C8	177.7 (2)	C22—C17—C18—C19	2.2 (3)
C1—C6—C7—C8	−1.4 (2)	N1—C17—C18—C19	−175.10 (18)
C5—C6—C7—C16	−4.4 (3)	C17—C18—C19—C20	0.1 (3)
C1—C6—C7—C16	176.51 (17)	C18—C19—C20—C21	−2.6 (3)
C16—C7—C8—N1	−176.80 (16)	C18—C19—C20—C23	175.09 (19)
C6—C7—C8—N1	1.2 (2)	C19—C20—C21—C22	2.9 (3)
C16—C7—C8—C9	8.5 (3)	C23—C20—C21—C22	−174.81 (18)
C6—C7—C8—C9	−173.51 (17)	C18—C17—C22—C21	−1.9 (3)
C1—N1—C8—C7	−0.5 (2)	N1—C17—C22—C21	175.46 (17)
C17—N1—C8—C7	169.21 (15)	C20—C21—C22—C17	−0.7 (3)
C1—N1—C8—C9	174.73 (16)

Cg is the centroid of the C17–C22 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9A···N2i	0.99	2.64	3.557 (3)	154
C14—H14···Cgii	0.95	2.84	3.735 (2)	157

Table 1

Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C17–C22 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C9—H9A⋯N2i	0.99	2.64	3.557 (3)	154
C14—H14⋯Cgii	0.95	2.84	3.735 (2)	157

Symmetry codes: (i) ; (ii) .