3-(4-Chloro­benzo­yl)-6-(4-chloro­phen­yl)-2,4-dimethyl­benzonitrile

Wang, X.; Zhang, Y.-M.; Jia, X.-F.

doi:10.1107/S1600536812036409

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 68| Part 9| September 2012| Page o2787

doi:10.1107/S1600536812036409

Open

access

3-(4-Chlorobenzoyl)-6-(4-chlorophenyl)-2,4-dimethylbenzonitrile

Xin Wang,^a,^b Yi-Min Zhang ^a ^* and Xue-Fei Jia ^a

^aSchool of Chemistry and Environmental Science, Henan Normal University, Xinxiang, Henan 453007, People's Republic of China, and ^bXinyang Agricultural College, Xinyang, Henan 464000, People's Republic of China
^*Correspondence e-mail: hxxzhym@sina.com

(Received 19 August 2012; accepted 21 August 2012; online 25 August 2012)

In the title compound, C₂₂H₁₅Cl₂NO, the terminal chlorobenzene rings are oriented at 44.51 (15) and 86.06 (17)° with respect to the central polysubstituted benzene ring, and make a dihedral angle of 49.48 (17)°with each other. In the crystal, molecules are linked by weak C—H⋯O and C—H⋯N interactions.

Related literature

For background to the title compound, see: Ma (2003 , 2005 , 2007 ); Hoffmann-Röder et al. (2004 ). For related structures, see: Zhang et al. (2011 ); Fun et al. (2012 ); Jagadeesan et al. (2011 ).

Experimental

Crystal data

C₂₂H₁₅Cl₂NO
M_r = 380.25
Monoclinic, P 2₁ /c
a = 7.8102 (12) Å
b = 30.032 (5) Å
c = 8.2054 (13) Å
β = 103.739 (2)°
V = 1869.6 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.36 mm⁻¹
T = 296 K
0.39 × 0.33 × 0.23 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2007 ) T_min = 0.873, T_max = 0.922
11684 measured reflections
3442 independent reflections
2013 reflections with I > 2σ(I)
R_int = 0.034

Refinement

R[F² > 2σ(F²)] = 0.047
wR(F²) = 0.121
S = 1.08
3442 reflections
237 parameters
H-atom parameters constrained
Δρ_max = 0.21 e Å⁻³
Δρ_min = −0.24 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯N1ⁱ	0.93	2.61	3.305 (5)	132
C5—H5⋯O1ⁱⁱ	0.93	2.53	3.390 (5)	155
Symmetry codes: (i) x-1, y, z; (ii) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

Data collection: SMART (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812036409/xu5613sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812036409/xu5613Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812036409/xu5613Isup3.cdx

Supporting information file. DOI: 10.1107/S1600536812036409/xu5613Isup4.cml

checkCIF report

Comment top

It has been well documented that benzenoid compounds are ubiquitous structural units in a wide variety of naturally occurring compounds and a plethora of pharmaceuticals. On the other hand, allene derivatives are powerful synthetic intermediates toward a plethora of important organic compounds and frequent building blocks of natural products (Ma, 2003, 2005, 2007; Hoffmann-Röder et al., 2004). In this regard, Zhang et al. have developed a novel and efficient method for the preparation of polysubstituted benzenes by one-pot double Michael addition/intramolecular aldol reaction/ decarboxylation of 1,2-allenic ketones with cyanoacetate (Zhang et al., 2011). Herein, we would like to report the structure of one of the products obtained by this method.

In the title compound (Fig. 1), all the bond lengths and bond angles are within normal ranges. The central polysubstituted benzene ring (C7—C12) forms dihedral angles of 44.51 (15)° and 86.06 (17)° with the other two chloro-substituted phenyl rings (C1—C6) and (C17—C22), respectively. And the dihedral angle between the two chloro-substituted phenyl rings, (C1—C7) and (C7—C12), is 49.48 (17)°. The mean plane of the ketone group is almost co-planar with the neighboring chloro-substituted phenyl ring (C17-C22).

In the crystal structure, the molecules are connected via C—H···O and C—H···N interactions.

Related literature top

For background to the title compound, see: Ma (2003, 2005, 2007); Hoffmann-Röder et al. (2004). For related structures, see: Zhang et al. (2011); Fun et al. (2012); Jagadeesan et al. (2011).

Experimental top

A mixture of 1-(4-chlorophenyl)buta-2,3-dien-1-one (1 mmol), cyanoacetate (0.5 mmol) and K₂CO₃ (0.5 mmol) in acetone (5 ml) was refluxed for 15 min. Upon completion, the reaction mixture was cooled to room temperature, added with water (10 ml) and extracted with ethyl acetate. The combined organic phases were washed with brine, dried, filtered and concentrated under vacuum. The residue was purified by column chromatography on silica gel eluting with ethyl acetate/hexane (1:20 v/v) to give the title compound as Colorless solids with a yield of 80%. Single crystals, suitable for X-ray diffraction analysis, were obtained by slow evaporation of solvent from a petroleum ether-dichloromethane (2:1 v/v) solution.

Computing details top

Data collection: SMART (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

Fig. 1. Molecular structure of the title compound, with displacement ellipsoids drawn at the 30% probability level.

Fig. 2. Crystal structure of the title compound, viewed along the a axis. Intermolecular C—H···O and C—H···N hydrogen bonds are shown as dashed lines, only H atoms involved in hydrogen bonds are shown.

3-(4-Chlorobenzoyl)-6-(4-chlorophenyl)-2,4-dimethylbenzonitrile top

Crystal data top

C₂₂H₁₅Cl₂NO	F(000) = 784
M_r = 380.25	D_x = 1.351 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3123 reflections
a = 7.8102 (12) Å	θ = 2.6–22.9°
b = 30.032 (5) Å	µ = 0.36 mm⁻¹
c = 8.2054 (13) Å	T = 296 K
β = 103.739 (2)°	Block, colourless
V = 1869.6 (5) Å³	0.39 × 0.33 × 0.23 mm
Z = 4

Data collection top

Bruker SMART CCD area-detector diffractometer	3442 independent reflections
Radiation source: fine-focus sealed tube	2013 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.034
phi and ω scans	θ_max = 25.5°, θ_min = 2.6°
Absorption correction: multi-scan (SADABS; Bruker, 2007)	h = −9→9
T_min = 0.873, T_max = 0.922	k = −36→36
11684 measured reflections	l = −9→9

Refinement top

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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.121	H-atom parameters constrained
S = 1.08	w = 1/[σ²(F_o²) + (0.0235P)² + 1.9216P] where P = (F_o² + 2F_c²)/3
3442 reflections	(Δ/σ)_max < 0.001
237 parameters	Δρ_max = 0.21 e Å⁻³
0 restraints	Δρ_min = −0.24 e Å⁻³

Crystal data top

C₂₂H₁₅Cl₂NO	V = 1869.6 (5) Å³
M_r = 380.25	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 7.8102 (12) Å	µ = 0.36 mm⁻¹
b = 30.032 (5) Å	T = 296 K
c = 8.2054 (13) Å	0.39 × 0.33 × 0.23 mm
β = 103.739 (2)°

Data collection top

Bruker SMART CCD area-detector diffractometer	3442 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2007)	2013 reflections with I > 2σ(I)
T_min = 0.873, T_max = 0.922	R_int = 0.034
11684 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.047	0 restraints
wR(F²) = 0.121	H-atom parameters constrained
S = 1.08	Δρ_max = 0.21 e Å⁻³
3442 reflections	Δρ_min = −0.24 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
C1	0.7995 (4)	0.21705 (10)	0.1502 (4)	0.0402 (7)
C2	0.6497 (4)	0.20687 (10)	0.2063 (4)	0.0452 (8)
H2	0.5945	0.2292	0.2535	0.054*
C3	0.5808 (4)	0.16426 (11)	0.1934 (4)	0.0525 (9)
H3	0.4806	0.1580	0.2318	0.063*
C4	0.6621 (5)	0.13136 (10)	0.1233 (4)	0.0518 (9)
C5	0.8084 (5)	0.14040 (11)	0.0632 (4)	0.0529 (9)
H5	0.8606	0.1181	0.0131	0.063*
C6	0.8767 (4)	0.18288 (10)	0.0779 (4)	0.0483 (8)
H6	0.9767	0.1889	0.0386	0.058*
C7	0.8714 (4)	0.26288 (10)	0.1663 (4)	0.0398 (7)
C8	1.0517 (4)	0.27148 (10)	0.2239 (4)	0.0442 (8)
C9	1.1199 (4)	0.31495 (11)	0.2343 (4)	0.0483 (8)
C10	1.0020 (4)	0.35035 (10)	0.1930 (4)	0.0460 (8)
C11	0.8210 (4)	0.34288 (10)	0.1389 (4)	0.0467 (8)
C12	0.7596 (4)	0.29920 (10)	0.1238 (4)	0.0451 (8)
H12	0.6394	0.2942	0.0838	0.054*
C13	1.1720 (5)	0.23601 (12)	0.2910 (5)	0.0558 (9)
C14	1.3152 (5)	0.32286 (14)	0.2910 (5)	0.0772 (12)
H14A	1.3698	0.3164	0.2005	0.116*
H14B	1.3639	0.3038	0.3845	0.116*
H14C	1.3365	0.3534	0.3241	0.116*
C15	0.6925 (5)	0.38100 (11)	0.0981 (5)	0.0646 (10)
H15A	0.5752	0.3695	0.0592	0.097*
H15B	0.7215	0.3991	0.0122	0.097*
H15C	0.6988	0.3986	0.1969	0.097*
C16	1.0722 (5)	0.39731 (11)	0.2256 (5)	0.0547 (9)
C17	1.1277 (4)	0.42252 (11)	0.0920 (4)	0.0495 (8)
C18	1.2013 (5)	0.46432 (11)	0.1290 (5)	0.0634 (10)
H18	1.2167	0.4758	0.2367	0.076*
C19	1.2517 (5)	0.48886 (12)	0.0070 (5)	0.0693 (11)
H19	1.3029	0.5167	0.0326	0.083*
C20	1.2263 (5)	0.47210 (11)	−0.1532 (5)	0.0589 (10)
C21	1.1562 (5)	0.43075 (11)	−0.1909 (5)	0.0658 (11)
H21	1.1412	0.4194	−0.2988	0.079*
C22	1.1076 (5)	0.40580 (11)	−0.0673 (5)	0.0619 (10)
H22	1.0608	0.3774	−0.0924	0.074*
Cl1	0.57545 (16)	0.07788 (3)	0.10760 (15)	0.0838 (4)
Cl2	1.28408 (16)	0.50406 (3)	−0.30697 (14)	0.0848 (4)
N1	1.2698 (4)	0.20909 (12)	0.3525 (5)	0.0805 (11)
O1	1.0819 (4)	0.41318 (9)	0.3638 (3)	0.0857 (9)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0442 (18)	0.0436 (17)	0.0329 (18)	0.0008 (14)	0.0092 (14)	0.0012 (14)
C2	0.049 (2)	0.0429 (18)	0.045 (2)	0.0041 (15)	0.0140 (16)	−0.0021 (15)
C3	0.055 (2)	0.051 (2)	0.054 (2)	−0.0044 (17)	0.0172 (17)	0.0015 (17)
C4	0.067 (2)	0.0420 (18)	0.045 (2)	−0.0002 (17)	0.0117 (18)	0.0021 (16)
C5	0.069 (2)	0.050 (2)	0.041 (2)	0.0109 (18)	0.0164 (18)	−0.0040 (16)
C6	0.057 (2)	0.0477 (19)	0.044 (2)	0.0038 (17)	0.0204 (17)	0.0003 (16)
C7	0.0453 (19)	0.0439 (18)	0.0323 (18)	−0.0010 (15)	0.0130 (15)	−0.0001 (14)
C8	0.045 (2)	0.0508 (19)	0.040 (2)	0.0009 (16)	0.0165 (15)	−0.0008 (15)
C9	0.046 (2)	0.061 (2)	0.039 (2)	−0.0086 (17)	0.0138 (16)	−0.0054 (16)
C10	0.057 (2)	0.0502 (19)	0.0314 (19)	−0.0099 (17)	0.0125 (16)	−0.0035 (14)
C11	0.058 (2)	0.0470 (19)	0.0354 (19)	−0.0021 (16)	0.0117 (16)	0.0022 (15)
C12	0.0446 (19)	0.0485 (19)	0.042 (2)	−0.0017 (16)	0.0095 (15)	0.0012 (15)
C13	0.050 (2)	0.062 (2)	0.059 (2)	0.0008 (19)	0.0207 (19)	0.0016 (19)
C14	0.054 (2)	0.085 (3)	0.090 (3)	−0.016 (2)	0.013 (2)	−0.010 (2)
C15	0.070 (3)	0.044 (2)	0.076 (3)	0.0014 (18)	0.011 (2)	0.0032 (18)
C16	0.063 (2)	0.055 (2)	0.048 (2)	−0.0154 (18)	0.0178 (18)	−0.0095 (18)
C17	0.059 (2)	0.0467 (18)	0.044 (2)	−0.0116 (17)	0.0144 (17)	−0.0070 (16)
C18	0.083 (3)	0.053 (2)	0.057 (2)	−0.023 (2)	0.021 (2)	−0.0158 (18)
C19	0.092 (3)	0.043 (2)	0.077 (3)	−0.022 (2)	0.030 (2)	−0.010 (2)
C20	0.070 (3)	0.045 (2)	0.066 (3)	−0.0041 (18)	0.026 (2)	0.0057 (18)
C21	0.094 (3)	0.053 (2)	0.056 (2)	−0.020 (2)	0.028 (2)	−0.0097 (18)
C22	0.082 (3)	0.049 (2)	0.058 (3)	−0.0240 (19)	0.022 (2)	−0.0079 (18)
Cl1	0.1082 (9)	0.0465 (5)	0.1010 (9)	−0.0146 (5)	0.0337 (7)	−0.0085 (5)
Cl2	0.1219 (10)	0.0556 (6)	0.0896 (8)	−0.0063 (6)	0.0505 (7)	0.0130 (5)
N1	0.065 (2)	0.083 (2)	0.095 (3)	0.018 (2)	0.023 (2)	0.014 (2)
O1	0.127 (3)	0.0814 (19)	0.0601 (19)	−0.0443 (17)	0.0442 (18)	−0.0276 (15)

Geometric parameters (Å, º) top

C1—C2	1.389 (4)	C12—H12	0.9300
C1—C6	1.393 (4)	C13—N1	1.144 (4)
C1—C7	1.481 (4)	C14—H14A	0.9600
C2—C3	1.382 (4)	C14—H14B	0.9600
C2—H2	0.9300	C14—H14C	0.9600
C3—C4	1.373 (4)	C15—H15A	0.9600
C3—H3	0.9300	C15—H15B	0.9600
C4—C5	1.374 (5)	C15—H15C	0.9600
C4—Cl1	1.736 (3)	C16—O1	1.216 (4)
C5—C6	1.377 (4)	C16—C17	1.479 (4)
C5—H5	0.9300	C17—C22	1.374 (4)
C6—H6	0.9300	C17—C18	1.384 (4)
C7—C12	1.389 (4)	C18—C19	1.373 (5)
C7—C8	1.398 (4)	C18—H18	0.9300
C8—C9	1.405 (4)	C19—C20	1.377 (5)
C8—C13	1.440 (5)	C19—H19	0.9300
C9—C10	1.395 (4)	C20—C21	1.363 (5)
C9—C14	1.504 (5)	C20—Cl2	1.729 (3)
C10—C11	1.396 (4)	C21—C22	1.384 (5)
C10—C16	1.514 (4)	C21—H21	0.9300
C11—C12	1.392 (4)	C22—H22	0.9300
C11—C15	1.507 (4)

C2—C1—C6	117.6 (3)	C11—C12—H12	118.8
C2—C1—C7	120.4 (3)	N1—C13—C8	176.2 (4)
C6—C1—C7	122.0 (3)	C9—C14—H14A	109.5
C3—C2—C1	121.4 (3)	C9—C14—H14B	109.5
C3—C2—H2	119.3	H14A—C14—H14B	109.5
C1—C2—H2	119.3	C9—C14—H14C	109.5
C4—C3—C2	119.2 (3)	H14A—C14—H14C	109.5
C4—C3—H3	120.4	H14B—C14—H14C	109.5
C2—C3—H3	120.4	C11—C15—H15A	109.5
C3—C4—C5	121.0 (3)	C11—C15—H15B	109.5
C3—C4—Cl1	119.1 (3)	H15A—C15—H15B	109.5
C5—C4—Cl1	119.9 (3)	C11—C15—H15C	109.5
C4—C5—C6	119.3 (3)	H15A—C15—H15C	109.5
C4—C5—H5	120.3	H15B—C15—H15C	109.5
C6—C5—H5	120.3	O1—C16—C17	121.8 (3)
C5—C6—C1	121.5 (3)	O1—C16—C10	118.0 (3)
C5—C6—H6	119.3	C17—C16—C10	120.2 (3)
C1—C6—H6	119.3	C22—C17—C18	119.2 (3)
C12—C7—C8	117.5 (3)	C22—C17—C16	122.0 (3)
C12—C7—C1	120.3 (3)	C18—C17—C16	118.8 (3)
C8—C7—C1	122.2 (3)	C19—C18—C17	120.2 (3)
C7—C8—C9	121.9 (3)	C19—C18—H18	119.9
C7—C8—C13	120.4 (3)	C17—C18—H18	119.9
C9—C8—C13	117.4 (3)	C18—C19—C20	119.9 (3)
C10—C9—C8	118.4 (3)	C18—C19—H19	120.1
C10—C9—C14	121.1 (3)	C20—C19—H19	120.1
C8—C9—C14	120.5 (3)	C21—C20—C19	120.6 (3)
C9—C10—C11	121.0 (3)	C21—C20—Cl2	120.0 (3)
C9—C10—C16	118.5 (3)	C19—C20—Cl2	119.4 (3)
C11—C10—C16	120.2 (3)	C20—C21—C22	119.5 (3)
C12—C11—C10	118.8 (3)	C20—C21—H21	120.3
C12—C11—C15	119.9 (3)	C22—C21—H21	120.3
C10—C11—C15	121.3 (3)	C17—C22—C21	120.6 (3)
C7—C12—C11	122.3 (3)	C17—C22—H22	119.7
C7—C12—H12	118.8	C21—C22—H22	119.7

C6—C1—C2—C3	1.0 (5)	C16—C10—C11—C12	−174.6 (3)
C7—C1—C2—C3	−179.6 (3)	C9—C10—C11—C15	178.5 (3)
C1—C2—C3—C4	−0.2 (5)	C16—C10—C11—C15	5.1 (5)
C2—C3—C4—C5	−1.2 (5)	C8—C7—C12—C11	−0.9 (4)
C2—C3—C4—Cl1	179.9 (3)	C1—C7—C12—C11	179.2 (3)
C3—C4—C5—C6	1.8 (5)	C10—C11—C12—C7	2.4 (5)
Cl1—C4—C5—C6	−179.4 (3)	C15—C11—C12—C7	−177.3 (3)
C4—C5—C6—C1	−0.9 (5)	C7—C8—C13—N1	−119 (6)
C2—C1—C6—C5	−0.4 (5)	C9—C8—C13—N1	55 (6)
C7—C1—C6—C5	−179.9 (3)	C9—C10—C16—O1	−86.8 (4)
C2—C1—C7—C12	−44.8 (4)	C11—C10—C16—O1	86.8 (4)
C6—C1—C7—C12	134.6 (3)	C9—C10—C16—C17	92.8 (4)
C2—C1—C7—C8	135.3 (3)	C11—C10—C16—C17	−93.6 (4)
C6—C1—C7—C8	−45.3 (4)	O1—C16—C17—C22	−176.1 (4)
C12—C7—C8—C9	−1.9 (4)	C10—C16—C17—C22	4.3 (5)
C1—C7—C8—C9	178.1 (3)	O1—C16—C17—C18	3.5 (6)
C12—C7—C8—C13	171.8 (3)	C10—C16—C17—C18	−176.1 (3)
C1—C7—C8—C13	−8.3 (4)	C22—C17—C18—C19	0.7 (6)
C7—C8—C9—C10	3.0 (5)	C16—C17—C18—C19	−179.0 (4)
C13—C8—C9—C10	−170.8 (3)	C17—C18—C19—C20	1.0 (6)
C7—C8—C9—C14	−177.8 (3)	C18—C19—C20—C21	−1.9 (6)
C13—C8—C9—C14	8.4 (5)	C18—C19—C20—Cl2	178.0 (3)
C8—C9—C10—C11	−1.4 (4)	C19—C20—C21—C22	1.1 (6)
C14—C9—C10—C11	179.4 (3)	Cl2—C20—C21—C22	−178.9 (3)
C8—C9—C10—C16	172.1 (3)	C18—C17—C22—C21	−1.5 (6)
C14—C9—C10—C16	−7.1 (5)	C16—C17—C22—C21	178.1 (4)
C9—C10—C11—C12	−1.2 (5)	C20—C21—C22—C17	0.6 (6)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···N1ⁱ	0.93	2.61	3.305 (5)	132
C5—H5···O1ⁱⁱ	0.93	2.53	3.390 (5)	155

Symmetry codes: (i) x−1, y, z; (ii) x, −y+1/2, z−1/2.

Experimental details

Crystal data
Chemical formula	C₂₂H₁₅Cl₂NO
M_r	380.25
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	7.8102 (12), 30.032 (5), 8.2054 (13)
β (°)	103.739 (2)
V (Å³)	1869.6 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.36
Crystal size (mm)	0.39 × 0.33 × 0.23

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2007)
T_min, T_max	0.873, 0.922
No. of measured, independent and observed [I > 2σ(I)] reflections	11684, 3442, 2013
R_int	0.034
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.047, 0.121, 1.08
No. of reflections	3442
No. of parameters	237
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.21, −0.24

Computer programs: SMART (Bruker, 2007), SAINT (Bruker, 2007), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···N1ⁱ	0.93	2.61	3.305 (5)	132.0
C5—H5···O1ⁱⁱ	0.93	2.53	3.390 (5)	155.0

Symmetry codes: (i) x−1, y, z; (ii) x, −y+1/2, z−1/2.

Acknowledgements

This work was supported by the National Natural Science Foundation of China (No. 21172057).

References

Bruker (2007). SADABS, SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Fun, H.-K., Loh, W.-S., Samshuddin, S., Narayana, B. & Sarojini, B. K. (2012). Acta Cryst. E68, o1877–o1878. CSD CrossRef IUCr Journals Google Scholar
Hoffmann-Röder, A. & Krause, N. (2004). Angew. Chem. Int. Ed. 43, 1196–1216. Google Scholar
Jagadeesan, G., Sethusankar, K., Sivasakthikumaran, R. & Mohanakrishnan, A. K. (2011). Acta Cryst. E67, o2177. Web of Science CSD CrossRef IUCr Journals Google Scholar
Ma, S. (2003). Acc. Chem. Res. 36, 701–712. Web of Science CrossRef PubMed CAS Google Scholar
Ma, S. (2005). Chem. Rev. 105, 2829–2871. Web of Science CrossRef PubMed Google Scholar
Ma, S. (2007). Aldrichim. Acta, 40, 91–102. CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Zhang, X., Jia, X., Fang, L., Liu, N., Wang, J. & Fan, X. (2011). Org. Lett. 13, 5024–5027. Web of Science CSD CrossRef CAS PubMed Google Scholar