2-Benzyl-6-chloro-1-(4-methyl­phen­yl)-1H-indole-3-carbonitrile

Yan, Q.; Qi, X.

doi:10.1107/S1600536811048422

organic compounds

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Volume 67| Part 12| December 2011| Page o3388

https://doi.org/10.1107/S1600536811048422

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2-Benzyl-6-chloro-1-(4-methylphenyl)-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 21 October 2011; accepted 15 November 2011; online 23 November 2011)

In the title compound, C₂₃H₁₇ClN₂, 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] interactions 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_r = 356.84
Monoclinic, P 2₁ /c
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[F² > 2σ(F²)] = 0.041
wR(F²) = 0.103
S = 0.85
4382 reflections
237 parameters
H-atom parameters constrained
Δρ_max = 0.35 e Å⁻³
Δρ_min = −0.30 e Å⁻³

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) -x+1, -y+1, -z; (ii) $[-x, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

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.

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536811048422/zl2420sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536811048422/zl2420Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536811048422/zl2420Isup3.cml

checkCIF report

Comment top

Indoles are widely applied in many fields such as pharmaceuticals. In order to disclose their structure-activity relationship, we have studied the crystal structures of a series of indole derivatives (Yan & Qi, 2011a,b,c). In our continuous investigation of indole derivatives, we herein report the structure of the title compound (Fig. 1). The indole ring forms an angle of 86.97 (8)° with the tolyl ring connected to the N1 atom. This is similar as in ethyl 2-benzyl-1-propyl-1H-indole-3-carboxylate [80.91 (5)°] reported by Yang et al. (2011), but greater than in 1-(4-methoxyphenyl)-2-methyl-1H-indole-3-carbonitrile [58.41 (4)°] (Yan & Qi, 2011a) and 1-(4-bromophenyl)-2-methyl-1H-indole-3-carbonitrile [58.85 (11)°] (Yan & Qi, 2011b) reported by our group. All bond distances and angles of the title compound are within the normal ranges (Allen et al., 1987).

In the crystal packing, a weak intermolecular hydrogen-bond interaction occurs, affording a dimer with the nitrile N atom being a hydrogen-bond acceptor and the methylene being a hydrogen-bond donor (Table 1 & Fig. 2). Significant C—H···π interaction exists between H14 and the aromatic C17—C22 ring (Cg) (Table 1). A short Cl···π interaction is detected between Cl1 and the other face of the same toyly ring. These C—H···π and Cl···π interactions link molecules into columns along the b axis (Fig. 3).

Related literature top

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 top

The title compound was prepared according to the method of the literature (Du et al., 2006). Colourless prisms of the title compound were grown by evaporation from a mixture of ethyl actate and petroleum ether.

Structure description top

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).

Computing details top

Data collection: CrystalClear-SM Expert (Rigaku, 2009); cell refinement: CrystalClear-SM Expert (Rigaku, 2009); data reduction: CrystalClear-SM Expert (Rigaku, 2009); 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 (Sheldrick, 2008).

Figures top

	Fig. 1. View of the title compound showing displacement ellipsoids at the 50% probability level.
	Fig. 2. Molecular packing of the title compound, viewed down the a axis. The C—H···N H-bonding is represented by dashed lines.
	Fig. 3. Molecular packing of the title compound, viewed down the c axis. The C—H···π and Cl···π interactions are represented by dashed lines.

2-Benzyl-6-chloro-1-(4-methylphenyl)-1H-indole-3-carbonitrile top

Crystal data top

C₂₃H₁₇ClN₂	F(000) = 744
M_r = 356.84	D_x = 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

Data collection top

Rigaku Saturn724 CCD diffractometer	4382 independent reflections
Radiation source: rotating anode	1947 reflections with I > 2σ(I)
Multilayer monochromator	R_int = 0.079
Detector resolution: 14.22 pixels mm^-1	θ_max = 28.0°, θ_min = 2.0°
ω and φ scans	h = −12→13
Absorption correction: multi-scan (CrystalClear-SM Expert; Rigaku, 2009)	k = −12→12
T_min = 0.958, T_max = 0.979	l = −24→24
18792 measured reflections

Refinement top

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(F_o²) + (0.0361P)²] where P = (F_o² + 2F_c²)/3
S = 0.85	(Δ/σ)_max < 0.001
4382 reflections	Δρ_max = 0.35 e Å⁻³
237 parameters	Δρ_min = −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)

Crystal data top

C₂₃H₁₇ClN₂	V = 1823.1 (3) Å³
M_r = 356.84	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 10.0003 (10) Å	µ = 0.22 mm⁻¹
b = 9.8565 (8) Å	T = 113 K
c = 18.539 (2) Å	0.20 × 0.16 × 0.10 mm
β = 93.926 (9)°

Data collection top

Rigaku Saturn724 CCD diffractometer	4382 independent reflections
Absorption correction: multi-scan (CrystalClear-SM Expert; Rigaku, 2009)	1947 reflections with I > 2σ(I)
T_min = 0.958, T_max = 0.979	R_int = 0.079
18792 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	0 restraints
wR(F²) = 0.103	H-atom parameters constrained
S = 0.85	Δρ_max = 0.35 e Å⁻³
4382 reflections	Δρ_min = −0.30 e Å⁻³
237 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
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) −x+1, −y+1, −z; (ii) −x, y−1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₂₃H₁₇ClN₂
M_r	356.84
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	113
a, b, c (Å)	10.0003 (10), 9.8565 (8), 18.539 (2)
β (°)	93.926 (9)
V (Å³)	1823.1 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.22
Crystal size (mm)	0.20 × 0.16 × 0.10

Data collection
Diffractometer	Rigaku Saturn724 CCD
Absorption correction	Multi-scan (CrystalClear-SM Expert; Rigaku, 2009)
T_min, T_max	0.958, 0.979
No. of measured, independent and observed [I > 2σ(I)] reflections	18792, 4382, 1947
R_int	0.079
(sin θ/λ)_max (Å⁻¹)	0.660

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.103, 0.85
No. of reflections	4382
No. of parameters	237
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.35, −0.30

Computer programs: CrystalClear-SM Expert (Rigaku, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

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) −x+1, −y+1, −z; (ii) −x, y−1/2, −z+1/2.

Acknowledgements

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

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19. CSD CrossRef Web of Science Google Scholar
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