Ethyl (E)-1-(2-styryl-1H-benzimidazol-1-yl)acetate

Fu, X.; Xu, G.

doi:10.1107/S1600536809019825

organic compounds

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Volume 65| Part 7| July 2009| Page o1535

doi:10.1107/S1600536809019825

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Ethyl (E)-1-(2-styryl-1H-benzimidazol-1-yl)acetate

Xue-qun Fu ^a ^* and Guang-hai Xu ^a

^aOrdered Matter Science Research Center, Southeast UniVersity, Nanjing 210096, People's Republic of China
^*Correspondence e-mail: fuxuequn222@163.com

(Received 23 May 2009; accepted 25 May 2009; online 10 June 2009)

In the title compound, C₁₉H₁₈NO₂, the dihedral angle between the benzimidazole and phenyl ring planes is 18.18 (17)°. The atoms of the ethyl side chain are disordered over two sets of sites in a 0.50:0.50 ratio. In the crystal, intermolecular C—H⋯O hydrogen bonds and C—H⋯π contacts help to consolidate the packing.

Related literature

For further synthetic details, see: Hang & Ye (2008 ). For background on benzimidazoles, see: Göker et al. (1999 ); Özbey et al. (1998 ).

Experimental

Crystal data

C₁₉H₁₈N₂O₂
M_r = 307.36
Orthorhombic, P c a 2₁
a = 12.021 (2) Å
b = 14.369 (3) Å
c = 9.7517 (18) Å
V = 1684.4 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 298 (2) K
0.25 × 0.25 × 0.20 mm

Data collection

Rigaku SCXmini diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005) T_min = 0.884, T_max = 0.984
16640 measured reflections
2046 independent reflections
1545 reflections with I > 2σ(I)
R_int = 0.056

Refinement

R[F² > 2σ(F²)] = 0.058
wR(F²) = 0.151
S = 1.07
2046 reflections
215 parameters
43 restraints
H-atom parameters constrained
Δρ_max = 0.16 e Å⁻³
Δρ_min = −0.25 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4—H4B⋯O1ⁱ	0.97	2.47	3.409 (4)	162
C4—H4A⋯Cg2ⁱⁱ	0.97	2.67	3.577 (4)	156
Symmetry codes: (i) $[-x+{\script{1\over 2}}, y, z+{\script{1\over 2}}]$ ; (ii) $[x+{\script{1\over 2}}, -y, z]$ ; (iii) $[-x, -y, z-{\script{1\over 2}}]$ .

Data collection: CrystalClear (Rigaku, 2005 ); cell refinement: CrystalClear; data reduction: CrystalClear; 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: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809019825/hb2982sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809019825/hb2982Isup2.hkl

checkCIF report

Comment top

The benzimidazole ring system is of great interest because of its diverse biological activities while the synthesis and crystal structure analyses of several benzimidazoles have already been reported (Göker et al., 1999; Özbey et al., 1998).

In the structure of the title compound (Fig. 1), the benzimidazole system is essentially planar (dihedral angle 1.17 (2)°). The dihedral angle between the benzimidazole and styryl groups is 17.78 (1)°. The molecule is twisted with the N1—C4—C3—O1 torsion angle of 13.61 (4)° between the ethyl acetate and benzimidazole groups.

In the crystal, intermolecular C—H···O hydrogen bonds (Fig.2) link the molecules to chains along the b axis. In addition the C—H···π contacts (Table 1) further stabilize the crystal structure.

Related literature top

For further synthetic details, see: Hang & Ye (2008). For background on benzimidazoles, see: Göker et al. (1999); Özbey et al. (1998). Cg2 is the centroid of the C5–C10 ring.

Experimental top

The synthesis of (E)-2-styryl-1H-benzimidazole was reported previously (Hang & Ye, 2008). Ethyl 2-bromoacetate (1.65 g. 10 mmol) was added to a solution of (E)-2-styryl-1H-benzo[d]imidazole (2.2 g,10 mmol) and NaH (0.6 g, 26 mmol) in THF (30 ml). After the mixture was stirred for 12 h at room temperature, the precipitate was filtered off and the solution was evaporated in vacuum. The crude product was then crystallized from ethanol to yield colourless prisms of (I).

Computing details top

Data collection: CrystalClear (Rigaku, 2005); cell refinement: CrystalClear (Rigaku, 2005); data reduction: CrystalClear (Rigaku, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of (I) with displacement ellipsoids drawn at the 30% probability level (all H atoms have been omitted for clarity).
	Fig. 2. A view of the packing of the title compound, stacking along the b axis. Dashed lines indicate hydrogen bonds.

Ethyl (E)-1-(2-styryl-1H-benzimidazol-1-yl)acetate top

Crystal data top

C₁₉H₁₈N₂O₂	F(000) = 652
M_r = 307.36	D_x = 1.212 Mg m⁻³
Orthorhombic, Pca2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2ac	Cell parameters from 3237 reflections
a = 12.021 (2) Å	θ = 2.5–27.5°
b = 14.369 (3) Å	µ = 0.08 mm⁻¹
c = 9.7517 (18) Å	T = 298 K
V = 1684.4 (5) Å³	Prism, colourless
Z = 4	0.25 × 0.25 × 0.20 mm

Data collection top

Rigaku SCXmini diffractometer	2046 independent reflections
Radiation source: fine-focus sealed tube	1545 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.056
Detector resolution: 13.6612 pixels mm^-1	θ_max = 27.5°, θ_min = 2.8°
CCD_Profile_fitting scans	h = −15→15
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	k = −18→18
T_min = 0.884, T_max = 0.984	l = −12→12
16640 measured reflections

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)] = 0.058	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.151	H-atom parameters constrained
S = 1.07	w = 1/[σ²(F_o²) + (0.0802P)² + 0.1398P] where P = (F_o² + 2F_c²)/3
2046 reflections
215 parameters	Δρ_max = 0.16 e Å⁻³
43 restraints	Δρ_min = −0.25 e Å⁻³

Crystal data top

C₁₉H₁₈N₂O₂	V = 1684.4 (5) Å³
M_r = 307.36	Z = 4
Orthorhombic, Pca2₁	Mo Kα radiation
a = 12.021 (2) Å	µ = 0.08 mm⁻¹
b = 14.369 (3) Å	T = 298 K
c = 9.7517 (18) Å	0.25 × 0.25 × 0.20 mm

Data collection top

Rigaku SCXmini diffractometer	2046 independent reflections
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	1545 reflections with I > 2σ(I)
T_min = 0.884, T_max = 0.984	R_int = 0.056
16640 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.058	43 restraints
wR(F²) = 0.151	H-atom parameters constrained
S = 1.07	Δρ_max = 0.16 e Å⁻³
2046 reflections	Δρ_min = −0.25 e Å⁻³
215 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	Occ. (<1)
N1	0.1633 (2)	0.13879 (18)	0.1323 (3)	0.0509 (6)
N2	0.0004 (2)	0.14329 (18)	0.0204 (3)	0.0558 (7)
C5	0.1630 (2)	0.0626 (2)	0.0454 (3)	0.0500 (7)
O1	0.3290 (2)	0.2529 (2)	0.0215 (3)	0.0743 (7)
O2	0.4352 (2)	0.2271 (2)	0.2042 (3)	0.0925 (10)
C3	0.3424 (3)	0.2197 (2)	0.1332 (4)	0.0570 (8)
C6	0.0611 (3)	0.0668 (2)	−0.0229 (4)	0.0543 (8)
C11	0.0644 (2)	0.1847 (2)	0.1111 (3)	0.0493 (7)
C12	0.0354 (3)	0.2693 (2)	0.1853 (4)	0.0559 (8)
H12A	0.0799	0.2873	0.2586	0.067*
C13	−0.0510 (3)	0.3216 (2)	0.1534 (4)	0.0587 (8)
H13A	−0.0924	0.3024	0.0780	0.070*
C14	−0.0894 (3)	0.4059 (2)	0.2221 (4)	0.0586 (8)
C4	0.2583 (3)	0.1664 (2)	0.2144 (3)	0.0539 (7)
H4A	0.2932	0.1113	0.2524	0.065*
H4B	0.2329	0.2046	0.2903	0.065*
C7	0.0364 (3)	−0.0019 (3)	−0.1204 (4)	0.0675 (10)
H7A	−0.0309	−0.0015	−0.1675	0.081*
C15	−0.1778 (4)	0.4562 (3)	0.1668 (5)	0.0794 (12)
H15A	−0.2105	0.4360	0.0856	0.095*
C19	−0.0430 (3)	0.4385 (3)	0.3420 (4)	0.0715 (10)
H19A	0.0171	0.4072	0.3806	0.086*
C9	0.2151 (4)	−0.0720 (3)	−0.0755 (4)	0.0763 (11)
H9A	0.2658	−0.1190	−0.0953	0.092*
C18	−0.0843 (4)	0.5169 (3)	0.4058 (5)	0.0863 (13)
H18A	−0.0519	0.5378	0.4867	0.104*
C8	0.1142 (4)	−0.0697 (3)	−0.1441 (5)	0.0804 (12)
H8A	0.0987	−0.1157	−0.2085	0.096*
C10	0.2420 (3)	−0.0058 (2)	0.0215 (4)	0.0652 (9)
H10A	0.3094	−0.0070	0.0684	0.078*
C16	−0.2178 (4)	0.5352 (3)	0.2300 (6)	0.0944 (14)
H16A	−0.2757	0.5686	0.1902	0.113*
C17	−0.1726 (5)	0.5644 (3)	0.3512 (6)	0.0941 (15)
H17A	−0.2015	0.6161	0.3962	0.113*
C1	0.5262 (14)	0.283 (2)	0.143 (3)	0.128 (3)	0.50
H1A	0.5213	0.2820	0.0437	0.153*	0.50
H1B	0.5218	0.3470	0.1738	0.153*	0.50
C2	0.628 (3)	0.241 (2)	0.188 (3)	0.137 (8)	0.50
H2B	0.6899	0.2732	0.1468	0.206*	0.50
H2C	0.6296	0.1769	0.1606	0.206*	0.50
H2D	0.6336	0.2453	0.2858	0.206*	0.50
C1'	0.5333 (14)	0.271 (2)	0.137 (3)	0.128 (3)	0.50
H1'A	0.5564	0.2338	0.0590	0.153*	0.50
H1'B	0.5147	0.3327	0.1058	0.153*	0.50
C2'	0.621 (3)	0.275 (2)	0.237 (3)	0.137 (8)	0.50
H2'A	0.6839	0.3070	0.1982	0.206*	0.50
H2'B	0.6429	0.2130	0.2622	0.206*	0.50
H2'C	0.5958	0.3078	0.3167	0.206*	0.50

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0473 (13)	0.0574 (15)	0.0480 (13)	−0.0008 (12)	−0.0054 (12)	−0.0040 (13)
N2	0.0486 (13)	0.0628 (16)	0.0560 (15)	−0.0030 (13)	−0.0017 (13)	−0.0031 (15)
C5	0.0513 (17)	0.0551 (17)	0.0434 (17)	−0.0044 (15)	0.0014 (14)	−0.0030 (14)
O1	0.0745 (16)	0.0925 (18)	0.0560 (14)	−0.0139 (14)	−0.0052 (14)	0.0121 (15)
O2	0.0618 (15)	0.125 (2)	0.090 (2)	−0.0270 (16)	−0.0254 (16)	0.043 (2)
C3	0.0547 (18)	0.0639 (19)	0.0525 (19)	−0.0027 (16)	−0.0054 (15)	−0.0003 (17)
C6	0.0513 (18)	0.0607 (18)	0.0510 (17)	−0.0093 (15)	0.0032 (14)	−0.0006 (16)
C11	0.0451 (16)	0.0533 (16)	0.0495 (17)	−0.0047 (14)	0.0063 (14)	0.0020 (15)
C12	0.0571 (19)	0.0557 (18)	0.0550 (19)	−0.0045 (16)	0.0044 (15)	0.0012 (16)
C13	0.0571 (19)	0.0631 (19)	0.0560 (19)	0.0008 (16)	−0.0026 (15)	−0.0011 (17)
C14	0.0614 (19)	0.0538 (17)	0.0604 (19)	0.0014 (16)	0.0056 (18)	0.0043 (17)
C4	0.0559 (18)	0.0615 (16)	0.0442 (15)	−0.0003 (17)	−0.0074 (15)	0.0007 (16)
C7	0.060 (2)	0.074 (2)	0.068 (2)	−0.0138 (19)	−0.0028 (18)	−0.015 (2)
C15	0.082 (3)	0.071 (2)	0.085 (3)	0.016 (2)	−0.010 (2)	−0.005 (2)
C19	0.075 (2)	0.073 (2)	0.067 (2)	0.0104 (19)	0.0006 (19)	−0.005 (2)
C9	0.082 (3)	0.068 (2)	0.079 (2)	0.010 (2)	0.002 (2)	−0.017 (2)
C18	0.105 (3)	0.080 (3)	0.074 (3)	0.006 (3)	−0.003 (3)	−0.016 (2)
C8	0.089 (3)	0.072 (2)	0.080 (3)	−0.010 (2)	0.000 (2)	−0.027 (2)
C10	0.0597 (18)	0.0716 (19)	0.064 (2)	0.0050 (18)	−0.0025 (18)	−0.0081 (19)
C16	0.100 (4)	0.082 (3)	0.101 (3)	0.034 (3)	−0.008 (3)	−0.003 (3)
C17	0.112 (4)	0.074 (3)	0.096 (3)	0.025 (3)	0.022 (3)	−0.004 (3)
C1	0.078 (3)	0.160 (7)	0.145 (6)	−0.048 (4)	−0.024 (4)	0.068 (6)
C2	0.086 (5)	0.18 (2)	0.151 (19)	−0.025 (9)	−0.005 (10)	0.031 (12)
C1'	0.078 (3)	0.160 (7)	0.145 (6)	−0.048 (4)	−0.024 (4)	0.068 (6)
C2'	0.086 (5)	0.18 (2)	0.151 (19)	−0.025 (9)	−0.005 (10)	0.031 (12)

Geometric parameters (Å, º) top

N1—C11	1.376 (4)	C15—H15A	0.9300
N1—C5	1.384 (4)	C19—C18	1.380 (6)
N1—C4	1.450 (4)	C19—H19A	0.9300
N2—C11	1.314 (4)	C9—C10	1.380 (5)
N2—C6	1.385 (4)	C9—C8	1.387 (6)
C5—C10	1.387 (5)	C9—H9A	0.9300
C5—C6	1.395 (4)	C18—C17	1.369 (7)
O1—C3	1.200 (5)	C18—H18A	0.9300
O2—C3	1.318 (4)	C8—H8A	0.9300
O2—C1	1.482 (9)	C10—H10A	0.9300
O2—C1'	1.485 (9)	C16—C17	1.367 (8)
C3—C4	1.495 (5)	C16—H16A	0.9300
C6—C7	1.402 (5)	C17—H17A	0.9300
C11—C12	1.457 (5)	C1—C2	1.434 (10)
C12—C13	1.318 (5)	C1—H1A	0.9700
C12—H12A	0.9300	C1—H1B	0.9700
C13—C14	1.459 (5)	C2—H2B	0.9600
C13—H13A	0.9300	C2—H2C	0.9600
C14—C19	1.378 (5)	C2—H2D	0.9600
C14—C15	1.393 (5)	C1'—C2'	1.436 (10)
C4—H4A	0.9700	C1'—H1'A	0.9700
C4—H4B	0.9700	C1'—H1'B	0.9700
C7—C8	1.370 (6)	C2'—H2'A	0.9600
C7—H7A	0.9300	C2'—H2'B	0.9600
C15—C16	1.378 (6)	C2'—H2'C	0.9600

C11—N1—C5	106.6 (2)	C10—C9—C8	121.3 (4)
C11—N1—C4	129.2 (3)	C10—C9—H9A	119.3
C5—N1—C4	123.8 (3)	C8—C9—H9A	119.3
C11—N2—C6	104.9 (3)	C17—C18—C19	120.7 (5)
N1—C5—C10	131.4 (3)	C17—C18—H18A	119.6
N1—C5—C6	105.1 (3)	C19—C18—H18A	119.6
C10—C5—C6	123.5 (3)	C7—C8—C9	122.2 (4)
C3—O2—C1	117.2 (11)	C7—C8—H8A	118.9
C3—O2—C1'	118.4 (10)	C9—C8—H8A	118.9
C1—O2—C1'	8 (3)	C9—C10—C5	116.3 (4)
O1—C3—O2	124.0 (3)	C9—C10—H10A	121.8
O1—C3—C4	126.4 (3)	C5—C10—H10A	121.8
O2—C3—C4	109.6 (3)	C17—C16—C15	120.0 (5)
N2—C6—C5	110.6 (3)	C17—C16—H16A	120.0
N2—C6—C7	130.8 (3)	C15—C16—H16A	120.0
C5—C6—C7	118.7 (3)	C16—C17—C18	119.4 (4)
N2—C11—N1	112.9 (3)	C16—C17—H17A	120.3
N2—C11—C12	124.9 (3)	C18—C17—H17A	120.3
N1—C11—C12	122.2 (3)	C2—C1—O2	106 (2)
C13—C12—C11	123.1 (3)	C2—C1—H1A	110.5
C13—C12—H12A	118.4	O2—C1—H1A	110.5
C11—C12—H12A	118.4	C2—C1—H1B	110.5
C12—C13—C14	127.9 (3)	O2—C1—H1B	110.5
C12—C13—H13A	116.1	H1A—C1—H1B	108.6
C14—C13—H13A	116.1	C1—C2—H2B	109.5
C19—C14—C15	117.4 (4)	C1—C2—H2C	109.5
C19—C14—C13	122.9 (3)	H2B—C2—H2C	109.5
C15—C14—C13	119.6 (3)	C1—C2—H2D	109.5
N1—C4—C3	112.3 (3)	H2B—C2—H2D	109.5
N1—C4—H4A	109.1	H2C—C2—H2D	109.5
C3—C4—H4A	109.1	C2'—C1'—O2	108 (2)
N1—C4—H4B	109.1	C2'—C1'—H1'A	110.1
C3—C4—H4B	109.1	O2—C1'—H1'A	110.1
H4A—C4—H4B	107.9	C2'—C1'—H1'B	110.1
C8—C7—C6	118.0 (4)	O2—C1'—H1'B	110.1
C8—C7—H7A	121.0	H1'A—C1'—H1'B	108.4
C6—C7—H7A	121.0	C1'—C2'—H2'A	109.5
C16—C15—C14	121.4 (5)	C1'—C2'—H2'B	109.5
C16—C15—H15A	119.3	H2'A—C2'—H2'B	109.5
C14—C15—H15A	119.3	C1'—C2'—H2'C	109.5
C14—C19—C18	121.0 (4)	H2'A—C2'—H2'C	109.5
C14—C19—H19A	119.5	H2'B—C2'—H2'C	109.5
C18—C19—H19A	119.5

C11—N1—C5—C10	178.2 (4)	C12—C13—C14—C15	174.9 (4)
C4—N1—C5—C10	4.8 (5)	C11—N1—C4—C3	−91.5 (4)
C11—N1—C5—C6	−0.8 (3)	C5—N1—C4—C3	80.3 (4)
C4—N1—C5—C6	−174.2 (3)	O1—C3—C4—N1	13.5 (5)
C1—O2—C3—O1	2.3 (17)	O2—C3—C4—N1	−167.8 (3)
C1'—O2—C3—O1	−6.5 (17)	N2—C6—C7—C8	178.9 (4)
C1—O2—C3—C4	−176.4 (16)	C5—C6—C7—C8	−0.3 (5)
C1'—O2—C3—C4	174.8 (16)	C19—C14—C15—C16	−0.4 (6)
C11—N2—C6—C5	0.7 (4)	C13—C14—C15—C16	178.8 (4)
C11—N2—C6—C7	−178.6 (4)	C15—C14—C19—C18	1.2 (6)
N1—C5—C6—N2	0.1 (3)	C13—C14—C19—C18	−177.9 (4)
C10—C5—C6—N2	−179.0 (3)	C14—C19—C18—C17	0.0 (7)
N1—C5—C6—C7	179.5 (3)	C6—C7—C8—C9	−0.1 (7)
C10—C5—C6—C7	0.4 (5)	C10—C9—C8—C7	0.4 (7)
C6—N2—C11—N1	−1.2 (4)	C8—C9—C10—C5	−0.3 (6)
C6—N2—C11—C12	180.0 (3)	N1—C5—C10—C9	−178.9 (3)
C5—N1—C11—N2	1.3 (4)	C6—C5—C10—C9	−0.1 (5)
C4—N1—C11—N2	174.2 (3)	C14—C15—C16—C17	−1.7 (8)
C5—N1—C11—C12	−179.8 (3)	C15—C16—C17—C18	2.9 (8)
C4—N1—C11—C12	−7.0 (5)	C19—C18—C17—C16	−2.0 (8)
N2—C11—C12—C13	−11.1 (5)	C3—O2—C1—C2	−147.8 (16)
N1—C11—C12—C13	170.2 (3)	C1'—O2—C1—C2	−47 (14)
C11—C12—C13—C14	178.3 (3)	C3—O2—C1'—C2'	177.1 (14)
C12—C13—C14—C19	−5.9 (6)	C1—O2—C1'—C2'	94 (16)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4B···O1ⁱ	0.97	2.47	3.409 (4)	162
C4—H4A···Cg2ⁱⁱ	0.97	2.67	3.577 (4)	156

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

Experimental details

Crystal data
Chemical formula	C₁₉H₁₈N₂O₂
M_r	307.36
Crystal system, space group	Orthorhombic, Pca2₁
Temperature (K)	298
a, b, c (Å)	12.021 (2), 14.369 (3), 9.7517 (18)
V (Å³)	1684.4 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.25 × 0.25 × 0.20

Data collection
Diffractometer	Rigaku SCXmini diffractometer
Absorption correction	Multi-scan (CrystalClear; Rigaku, 2005)
T_min, T_max	0.884, 0.984
No. of measured, independent and observed [I > 2σ(I)] reflections	16640, 2046, 1545
R_int	0.056
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.058, 0.151, 1.07
No. of reflections	2046
No. of parameters	215
No. of restraints	43
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.16, −0.25

Computer programs: CrystalClear (Rigaku, 2005), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4B···O1ⁱ	0.97	2.47	3.409 (4)	161.5
C4—H4A···Cg2ⁱⁱ	0.97	2.6702	3.577 (4)	155.90

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

Acknowledgements

The authors are grateful to the starter fund of Southeast University for financial support to purchase the X-ray diffractometer.

References

Göker, H., Ayhan-Kõlcõgil, G., Tuncëbilek, M., Kusë, C., Ertan, R., Kendi, E., Özbey, S., Fort, M., Garcia, C. & Farre, A. (1999). J. Heterocycl. Chem. 51, 2561–2573. Google Scholar
Hang, T. & Ye, Q. (2008). Acta Cryst. E64, o964. Web of Science CSD CrossRef IUCr Journals Google Scholar
Özbey, S., Kendi, E., Göker, H. & Tuncëbilek, M. (1998). J. Chem. Crystallogr. 28, 461–464. Google Scholar
Rigaku (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar