organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890

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

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[Du, Y., Liu, R., Linn, G. & Zhao, K. (2006). Org. Lett. 8, 5919-5922.]). For its precursor, see: Jin et al. (2009[Jin, H., Li, P., Liu, B. & Cheng, X. (2009). Acta Cryst. E65, o236.]). For related structures, see: Yang et al. (2011[Yang, K., Li, P.-F., Liu, Y. & Fang, Z.-Z. (2011). Acta Cryst. E67, o1041.]); Yan & Qi (2011a[Yan, Q. & Qi, X. (2011a). Acta Cryst. E67, o2312.],b[Yan, Q. & Qi, X. (2011b). Acta Cryst. E67, o2509.],c[Yan, Q. & Qi, X. (2011c). Acta Cryst. E67, o2798.]). For standard bond lengths, see: Allen et al. (1987[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.]).

[Scheme 1]

Experimental

Crystal data
  • C23H17ClN2

  • Mr = 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[Rigaku (2009). CrystalClear-SM Expert. Rigaku Corporation, Tokyo, Japan.]) Tmin = 0.958, Tmax = 0.979

  • 18792 measured reflections

  • 4382 independent reflections

  • 1947 reflections with I > 2σ(I)

  • Rint = 0.079

Refinement
  • R[F2 > 2σ(F2)] = 0.041

  • wR(F2) = 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

Table 1
Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C17–C22 ring.

D—H⋯A D—H H⋯A DA 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[Rigaku (2009). CrystalClear-SM Expert. Rigaku Corporation, Tokyo, Japan.]); cell refinement: CrystalClear-SM Expert; data reduction: CrystalClear-SM Expert; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXL97.

Supporting information


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.

Refinement top

All H atoms were positioned geometrically (C—H = 0.95, 0.98 and 0.99 Å) and refined as riding with Uiso(H) = 1.2Ueq(CH & CH2) or 1.5Ueq(CH3).

Structure description 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).

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
[Figure 1] Fig. 1. View of the title compound showing displacement ellipsoids at the 50% probability level.
[Figure 2] Fig. 2. Molecular packing of the title compound, viewed down the a axis. The C—H···N H-bonding is represented by dashed lines.
[Figure 3] 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
C23H17ClN2F(000) = 744
Mr = 356.84Dx = 1.300 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 6077 reflections
a = 10.0003 (10) Åθ = 2.0–28.0°
b = 9.8565 (8) ŵ = 0.22 mm1
c = 18.539 (2) ÅT = 113 K
β = 93.926 (9)°Prism, colorless
V = 1823.1 (3) Å30.20 × 0.16 × 0.10 mm
Z = 4
Data collection top
Rigaku Saturn724 CCD
diffractometer
4382 independent reflections
Radiation source: rotating anode1947 reflections with I > 2σ(I)
Multilayer monochromatorRint = 0.079
Detector resolution: 14.22 pixels mm-1θmax = 28.0°, θmin = 2.0°
ω and φ scansh = 1213
Absorption correction: multi-scan
(CrystalClear-SM Expert; Rigaku, 2009)
k = 1212
Tmin = 0.958, Tmax = 0.979l = 2424
18792 measured reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.041H-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 reflectionsΔρmax = 0.35 e Å3
237 parametersΔρmin = 0.30 e Å3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0033 (5)
Crystal data top
C23H17ClN2V = 1823.1 (3) Å3
Mr = 356.84Z = 4
Monoclinic, P21/cMo Kα radiation
a = 10.0003 (10) ŵ = 0.22 mm1
b = 9.8565 (8) ÅT = 113 K
c = 18.539 (2) Å0.20 × 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)
Tmin = 0.958, Tmax = 0.979Rint = 0.079
18792 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0410 restraints
wR(F2) = 0.103H-atom parameters constrained
S = 0.85Δρmax = 0.35 e Å3
4382 reflectionsΔρmin = 0.30 e Å3
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
xyzUiso*/Ueq
Cl10.03716 (5)1.21324 (5)0.09402 (3)0.03050 (16)
N10.12552 (15)0.71133 (16)0.10904 (7)0.0212 (4)
N20.54914 (18)0.70088 (18)0.00901 (9)0.0377 (5)
C10.13022 (19)0.84896 (19)0.09184 (9)0.0212 (4)
C20.0363 (2)0.94986 (19)0.10034 (9)0.0231 (5)
H20.04850.93120.11840.028*
C30.0728 (2)1.0788 (2)0.08114 (9)0.0238 (5)
C40.19515 (19)1.1085 (2)0.05278 (9)0.0260 (5)
H40.21591.19920.04030.031*
C50.2855 (2)1.0062 (2)0.04304 (10)0.0251 (5)
H50.36841.02530.02300.030*
C60.25444 (19)0.8741 (2)0.06279 (9)0.0216 (4)
C70.32207 (19)0.7456 (2)0.06210 (9)0.0230 (5)
C80.24230 (19)0.6490 (2)0.09126 (9)0.0236 (5)
C90.27113 (19)0.50407 (19)0.10918 (10)0.0252 (5)
H9A0.34310.47120.07950.030*
H9B0.18990.44930.09660.030*
C100.31403 (19)0.4831 (2)0.18884 (10)0.0235 (5)
C110.4009 (2)0.5740 (2)0.22559 (11)0.0303 (5)
H110.43270.65090.20100.036*
C120.4411 (2)0.5531 (2)0.29759 (11)0.0371 (6)
H120.50070.61540.32210.044*
C130.3951 (2)0.4425 (2)0.33395 (11)0.0387 (6)
H130.42230.42900.38350.046*
C140.3092 (2)0.3513 (2)0.29807 (11)0.0397 (6)
H140.27780.27460.32290.048*
C150.2687 (2)0.3716 (2)0.22582 (11)0.0344 (5)
H150.20950.30870.20150.041*
C160.4488 (2)0.7192 (2)0.03379 (10)0.0268 (5)
C170.00947 (19)0.6386 (2)0.12952 (9)0.0220 (4)
C180.0077 (2)0.6062 (2)0.20068 (10)0.0328 (5)
H180.05410.63780.23810.039*
C190.1160 (2)0.5272 (2)0.21686 (11)0.0384 (6)
H190.12790.50510.26590.046*
C200.2076 (2)0.4795 (2)0.16341 (11)0.0290 (5)
C210.1911 (2)0.5178 (2)0.09294 (10)0.0286 (5)
H210.25510.48980.05570.034*
C220.0833 (2)0.59617 (19)0.07563 (10)0.0249 (5)
H220.07300.62080.02680.030*
C230.3186 (2)0.3845 (2)0.18130 (12)0.0472 (7)
H23A0.39890.40380.14960.071*
H23B0.33890.39740.23180.071*
H23C0.29040.29060.17410.071*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0339 (3)0.0245 (3)0.0329 (3)0.0083 (3)0.0016 (2)0.0004 (2)
N10.0207 (9)0.0196 (9)0.0233 (8)0.0016 (8)0.0017 (7)0.0009 (7)
N20.0329 (11)0.0306 (11)0.0507 (12)0.0012 (10)0.0121 (9)0.0055 (9)
C10.0258 (11)0.0186 (10)0.0186 (9)0.0005 (10)0.0025 (8)0.0004 (8)
C20.0237 (11)0.0250 (11)0.0201 (10)0.0017 (9)0.0013 (8)0.0017 (9)
C30.0273 (12)0.0218 (11)0.0218 (10)0.0062 (10)0.0027 (8)0.0017 (8)
C40.0303 (12)0.0212 (11)0.0259 (10)0.0000 (10)0.0011 (9)0.0008 (9)
C50.0251 (12)0.0255 (12)0.0248 (10)0.0005 (10)0.0014 (8)0.0002 (9)
C60.0227 (11)0.0211 (11)0.0205 (10)0.0016 (9)0.0016 (8)0.0009 (8)
C70.0214 (11)0.0232 (12)0.0245 (10)0.0023 (9)0.0014 (8)0.0032 (8)
C80.0266 (12)0.0221 (11)0.0217 (9)0.0052 (10)0.0012 (8)0.0053 (9)
C90.0249 (12)0.0218 (11)0.0287 (11)0.0001 (10)0.0004 (9)0.0045 (9)
C100.0198 (11)0.0211 (11)0.0297 (11)0.0053 (9)0.0020 (8)0.0014 (9)
C110.0317 (13)0.0227 (12)0.0360 (12)0.0037 (10)0.0008 (10)0.0023 (9)
C120.0389 (14)0.0317 (13)0.0387 (13)0.0050 (11)0.0107 (10)0.0059 (11)
C130.0474 (15)0.0377 (14)0.0303 (12)0.0129 (12)0.0036 (11)0.0014 (10)
C140.0456 (15)0.0351 (14)0.0387 (13)0.0022 (13)0.0044 (11)0.0105 (11)
C150.0350 (13)0.0285 (13)0.0394 (12)0.0016 (11)0.0005 (10)0.0007 (10)
C160.0317 (13)0.0177 (11)0.0310 (11)0.0018 (10)0.0011 (9)0.0025 (9)
C170.0230 (11)0.0197 (11)0.0234 (10)0.0043 (9)0.0023 (8)0.0028 (8)
C180.0313 (13)0.0446 (14)0.0222 (11)0.0006 (11)0.0016 (9)0.0002 (10)
C190.0360 (14)0.0543 (16)0.0259 (11)0.0043 (13)0.0097 (10)0.0115 (11)
C200.0264 (12)0.0227 (12)0.0387 (12)0.0083 (10)0.0092 (10)0.0043 (10)
C210.0289 (12)0.0266 (12)0.0300 (11)0.0008 (10)0.0004 (9)0.0045 (9)
C220.0304 (12)0.0239 (11)0.0207 (10)0.0009 (10)0.0032 (8)0.0006 (9)
C230.0372 (15)0.0389 (15)0.0681 (17)0.0018 (13)0.0230 (12)0.0092 (13)
Geometric parameters (Å, º) top
Cl1—C31.7487 (19)C11—C121.383 (3)
N1—C81.379 (2)C11—H110.9500
N1—C11.395 (2)C12—C131.377 (3)
N1—C171.437 (2)C12—H120.9500
N2—C161.146 (2)C13—C141.382 (3)
C1—C21.385 (2)C13—H130.9500
C1—C61.409 (2)C14—C151.387 (3)
C2—C31.375 (2)C14—H140.9500
C2—H20.9500C15—H150.9500
C3—C41.396 (3)C17—C181.379 (2)
C4—C51.374 (2)C17—C221.381 (2)
C4—H40.9500C18—C191.384 (3)
C5—C61.393 (3)C18—H180.9500
C5—H50.9500C19—C201.385 (3)
C6—C71.436 (3)C19—H190.9500
C7—C81.376 (3)C20—C211.381 (3)
C7—C161.428 (3)C20—C231.506 (3)
C8—C91.490 (3)C21—C221.382 (3)
C9—C101.523 (2)C21—H210.9500
C9—H9A0.9900C22—H220.9500
C9—H9B0.9900C23—H23A0.9800
C10—C151.387 (3)C23—H23B0.9800
C10—C111.393 (3)C23—H23C0.9800
C8—N1—C1109.63 (16)C10—C11—H11119.8
C8—N1—C17123.60 (16)C13—C12—C11120.4 (2)
C1—N1—C17125.86 (16)C13—C12—H12119.8
C2—C1—N1129.70 (18)C11—C12—H12119.8
C2—C1—C6122.68 (18)C12—C13—C14119.8 (2)
N1—C1—C6107.61 (17)C12—C13—H13120.1
C3—C2—C1116.10 (18)C14—C13—H13120.1
C3—C2—H2121.9C13—C14—C15120.1 (2)
C1—C2—H2121.9C13—C14—H14119.9
C2—C3—C4123.12 (19)C15—C14—H14119.9
C2—C3—Cl1118.98 (16)C14—C15—C10120.5 (2)
C4—C3—Cl1117.89 (15)C14—C15—H15119.7
C5—C4—C3119.79 (19)C10—C15—H15119.7
C5—C4—H4120.1N2—C16—C7177.6 (2)
C3—C4—H4120.1C18—C17—C22120.01 (19)
C4—C5—C6119.39 (19)C18—C17—N1121.59 (17)
C4—C5—H5120.3C22—C17—N1118.34 (16)
C6—C5—H5120.3C17—C18—C19119.23 (19)
C5—C6—C1118.87 (18)C17—C18—H18120.4
C5—C6—C7135.07 (18)C19—C18—H18120.4
C1—C6—C7106.05 (17)C18—C19—C20121.69 (19)
C8—C7—C16124.79 (18)C18—C19—H19119.2
C8—C7—C6108.70 (16)C20—C19—H19119.2
C16—C7—C6126.47 (18)C21—C20—C19117.9 (2)
C7—C8—N1107.99 (17)C21—C20—C23121.1 (2)
C7—C8—C9129.96 (18)C19—C20—C23120.98 (19)
N1—C8—C9121.84 (18)C20—C21—C22121.22 (19)
C8—C9—C10112.56 (15)C20—C21—H21119.4
C8—C9—H9A109.1C22—C21—H21119.4
C10—C9—H9A109.1C17—C22—C21119.84 (18)
C8—C9—H9B109.1C17—C22—H22120.1
C10—C9—H9B109.1C21—C22—H22120.1
H9A—C9—H9B107.8C20—C23—H23A109.5
C15—C10—C11118.79 (19)C20—C23—H23B109.5
C15—C10—C9120.45 (18)H23A—C23—H23B109.5
C11—C10—C9120.75 (18)C20—C23—H23C109.5
C12—C11—C10120.42 (19)H23A—C23—H23C109.5
C12—C11—H11119.8H23B—C23—H23C109.5
C8—N1—C1—C2179.86 (18)C17—N1—C8—C915.6 (3)
C17—N1—C1—C210.8 (3)C7—C8—C9—C1097.8 (2)
C8—N1—C1—C60.43 (19)N1—C8—C9—C1076.2 (2)
C17—N1—C1—C6169.82 (15)C8—C9—C10—C15140.01 (19)
N1—C1—C2—C3177.05 (17)C8—C9—C10—C1140.9 (2)
C6—C1—C2—C32.3 (3)C15—C10—C11—C120.1 (3)
C1—C2—C3—C41.7 (3)C9—C10—C11—C12178.96 (17)
C1—C2—C3—Cl1177.16 (13)C10—C11—C12—C130.4 (3)
C2—C3—C4—C50.1 (3)C11—C12—C13—C140.6 (3)
Cl1—C3—C4—C5178.81 (14)C12—C13—C14—C150.4 (3)
C3—C4—C5—C61.0 (3)C13—C14—C15—C100.1 (3)
C4—C5—C6—C10.5 (3)C11—C10—C15—C140.0 (3)
C4—C5—C6—C7178.58 (19)C9—C10—C15—C14179.10 (18)
C2—C1—C6—C51.3 (3)C8—N1—C17—C1889.9 (2)
N1—C1—C6—C5178.18 (15)C1—N1—C17—C18102.1 (2)
C2—C1—C6—C7179.42 (16)C8—N1—C17—C2287.5 (2)
N1—C1—C6—C71.11 (19)C1—N1—C17—C2280.5 (2)
C5—C6—C7—C8177.7 (2)C22—C17—C18—C192.2 (3)
C1—C6—C7—C81.4 (2)N1—C17—C18—C19175.10 (18)
C5—C6—C7—C164.4 (3)C17—C18—C19—C200.1 (3)
C1—C6—C7—C16176.51 (17)C18—C19—C20—C212.6 (3)
C16—C7—C8—N1176.80 (16)C18—C19—C20—C23175.09 (19)
C6—C7—C8—N11.2 (2)C19—C20—C21—C222.9 (3)
C16—C7—C8—C98.5 (3)C23—C20—C21—C22174.81 (18)
C6—C7—C8—C9173.51 (17)C18—C17—C22—C211.9 (3)
C1—N1—C8—C70.5 (2)N1—C17—C22—C21175.46 (17)
C17—N1—C8—C7169.21 (15)C20—C21—C22—C170.7 (3)
C1—N1—C8—C9174.73 (16)
Hydrogen-bond geometry (Å, º) top
Cg is the centroid of the C17–C22 ring.
D—H···AD—HH···AD···AD—H···A
C9—H9A···N2i0.992.643.557 (3)154
C14—H14···Cgii0.952.843.735 (2)157
Symmetry codes: (i) x+1, y+1, z; (ii) x, y1/2, z+1/2.

Experimental details

Crystal data
Chemical formulaC23H17ClN2
Mr356.84
Crystal system, space groupMonoclinic, P21/c
Temperature (K)113
a, b, c (Å)10.0003 (10), 9.8565 (8), 18.539 (2)
β (°) 93.926 (9)
V3)1823.1 (3)
Z4
Radiation typeMo Kα
µ (mm1)0.22
Crystal size (mm)0.20 × 0.16 × 0.10
Data collection
DiffractometerRigaku Saturn724 CCD
Absorption correctionMulti-scan
(CrystalClear-SM Expert; Rigaku, 2009)
Tmin, Tmax0.958, 0.979
No. of measured, independent and
observed [I > 2σ(I)] reflections
18792, 4382, 1947
Rint0.079
(sin θ/λ)max1)0.660
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.041, 0.103, 0.85
No. of reflections4382
No. of parameters237
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)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···AD—HH···AD···AD—H···A
C9—H9A···N2i0.992.643.557 (3)154
C14—H14···Cgii0.952.843.735 (2)157
Symmetry codes: (i) x+1, y+1, z; (ii) x, y1/2, z+1/2.
 

Acknowledgements

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

References

First citationAllen, 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
First citationDu, Y., Liu, R., Linn, G. & Zhao, K. (2006). Org. Lett. 8, 5919–5922.  Web of Science CSD CrossRef PubMed CAS Google Scholar
First citationJin, H., Li, P., Liu, B. & Cheng, X. (2009). Acta Cryst. E65, o236.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationRigaku (2009). CrystalClear-SM Expert. Rigaku Corporation, Tokyo, Japan.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationYan, Q. & Qi, X. (2011a). Acta Cryst. E67, o2312.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationYan, Q. & Qi, X. (2011b). Acta Cryst. E67, o2509.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationYan, Q. & Qi, X. (2011c). Acta Cryst. E67, o2798.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationYang, K., Li, P.-F., Liu, Y. & Fang, Z.-Z. (2011). Acta Cryst. E67, o1041.  Web of Science CSD CrossRef IUCr Journals Google Scholar

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