Ethyl 1-(4-chloro­benz­yl)-3-phenyl-1H-pyrazole-5-carboxyl­ate

Hao, B.-Q.; Xu, W.-R.; Meng, F.-C.; Duan, G.-Y.

doi:10.1107/S1600536812007428

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 68| Part 3| March 2012| Page o877

doi:10.1107/S1600536812007428

Open

access

Ethyl 1-(4-chlorobenzyl)-3-phenyl-1H-pyrazole-5-carboxylate

Ben-Qian Hao,^a Wei-Ren Xu,^b Fan-Cui Meng ^b and Gui-Yun Duan ^a ^*

^aTaishan Medical College, Tai an 271016, People's Republic of China, and ^bTianjin Institute of Pharmaceutical Research, Tian Jin 300193, People's Republic of China
^*Correspondence e-mail: yqge@yahoo.cn

(Received 8 February 2012; accepted 19 February 2012; online 29 February 2012)

In the title compound, C₁₉H₁₇ClN₂O₂, the pyrazole ring makes dihedral angles of 6.97 (5) and 79.25 (1)°, respectively, with the phenyl and chlorophenyl rings, respectively. In the crystal, C—H⋯O hydrogen bonds are observed.

Related literature

For background to the title compound, see: Ge et al. (2007 , 2009 , 2011 ). For a related compound, see: Xia et al. (2007 ).

Experimental

Crystal data

C₁₉H₁₇ClN₂O₂
M_r = 340.80
Triclinic, $[P \overline 1]$
a = 8.1815 (10) Å
b = 10.4039 (12) Å
c = 11.0969 (13) Å
α = 109.981 (2)°
β = 90.107 (2)°
γ = 104.046 (2)°
V = 857.43 (18) Å³
Z = 2
Mo Kα radiation
μ = 0.24 mm⁻¹
T = 298 K
0.26 × 0.24 × 0.20 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2003 ) T_min = 0.941, T_max = 0.954
4495 measured reflections
3008 independent reflections
2554 reflections with I > 2σ(I)
R_int = 0.023

Refinement

R[F² > 2σ(F²)] = 0.039
wR(F²) = 0.107
S = 1.03
3008 reflections
218 parameters
H-atom parameters constrained
Δρ_max = 0.25 e Å⁻³
Δρ_min = −0.30 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6⋯O1ⁱ	0.93	2.56	3.281 (2)	135
C1—H1B⋯O1	0.97	2.42	2.921 (2)	111
Symmetry code: (i) -x+2, -y+1, -z+1.

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

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812007428/zj2059sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812007428/zj2059Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812007428/zj2059Isup3.cml

checkCIF report

Comment top

Synthesis of nitrogen-containing heterocyclic compounds has been a subject of great interest due to the wide application in agrochemical and pharmaceutical fields (Ge et al., 2009, 2011). Some pyrazole derivatives which belong to this category have been of interest for their biological activities. Considerable efforts have been devoted to the development of novel pyrazole compounds. The title pyrazole (I) (Fig. 1) was synthesized in order to study and compare its biological properties with other related compounds (Xia et al., 2007). (I) was screened for anticancer activities and found to be inactive. We report here the crystal structure of the title compound. In the title compound, C₁₉H₁₇ClN₂O₂, all bond lengths and angles show normal values. The pyrazole ring makes dihedral angles of 6.97° and 79.25°, respectively, with the C14–C19 and C2–C7 phenyl rings. There existed intermolecule C—H···O hydrogen bonds to stablized the crystal structure.

Related literature top

For background to the title compound, see: Ge et al. (2007, 2009, 2011). For a related compound, see: Xia et al. (2007). [Please check amended text]

Experimental top

A mixture of ethyl 3-phenyl-1H-pyrazole-5-carboxylate (0.02 mol), 1-chloro-4-(chloromethyl)benzene (0.0024 mol) and potassium carbonate (0.02 mol) in acetonitrile (100 ml) was heated to reflux for 3 h. The solvent was removed under reduced pressure and a product was isolated by column chromatography on silica gel (yield 82%). Crystals of (I) suitable for X-ray diffraction were obtained by allowing a refluxed solution of the product in ethyl acetate (0.10 M) to cool slowly to room temperature (without temperature control) and allowing the solvent to evaporate for 2 d.

Computing details top

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

Figures top

	Fig. 1. The molecular structure of (I), showing displacement ellipsoids drawn at the 50% probability level.
	Fig. 2. A packing diagram for (I).

Ethyl 1-(4-chlorobenzyl)-3-phenyl-1H-pyrazole-5-carboxylate top

Crystal data top

C₁₉H₁₇ClN₂O₂	Z = 2
M_r = 340.80	F(000) = 356
Triclinic, P1	D_x = 1.320 Mg m⁻³
a = 8.1815 (10) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.4039 (12) Å	Cell parameters from 2727 reflections
c = 11.0969 (13) Å	θ = 2.4–28.2°
α = 109.981 (2)°	µ = 0.24 mm⁻¹
β = 90.107 (2)°	T = 298 K
γ = 104.046 (2)°	Block, white
V = 857.43 (18) Å³	0.26 × 0.24 × 0.20 mm

Data collection top

Bruker SMART CCD diffractometer	3008 independent reflections
Radiation source: fine-focus sealed tube	2554 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.023
ϕ and ω scans	θ_max = 25.1°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	h = −9→9
T_min = 0.941, T_max = 0.954	k = −11→12
4495 measured reflections	l = −11→13

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)] = 0.039	H-atom parameters constrained
wR(F²) = 0.107	w = 1/[σ²(F_o²) + (0.0481P)² + 0.2205P] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max < 0.001
3008 reflections	Δρ_max = 0.25 e Å⁻³
218 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: 0.082 (5)

Crystal data top

C₁₉H₁₇ClN₂O₂	γ = 104.046 (2)°
M_r = 340.80	V = 857.43 (18) Å³
Triclinic, P1	Z = 2
a = 8.1815 (10) Å	Mo Kα radiation
b = 10.4039 (12) Å	µ = 0.24 mm⁻¹
c = 11.0969 (13) Å	T = 298 K
α = 109.981 (2)°	0.26 × 0.24 × 0.20 mm
β = 90.107 (2)°

Data collection top

Bruker SMART CCD diffractometer	3008 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	2554 reflections with I > 2σ(I)
T_min = 0.941, T_max = 0.954	R_int = 0.023
4495 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.039	0 restraints
wR(F²) = 0.107	H-atom parameters constrained
S = 1.03	Δρ_max = 0.25 e Å⁻³
3008 reflections	Δρ_min = −0.30 e Å⁻³
218 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	1.50815 (7)	0.95990 (7)	0.77388 (6)	0.0839 (2)
O1	0.84683 (18)	0.38892 (14)	0.64732 (11)	0.0665 (4)
O2	0.85747 (17)	0.25171 (13)	0.76392 (11)	0.0598 (3)
N1	0.75907 (17)	0.58814 (15)	0.87794 (13)	0.0492 (3)
N2	0.71786 (18)	0.65423 (15)	0.99660 (13)	0.0514 (4)
C1	0.7812 (2)	0.6630 (2)	0.78600 (17)	0.0561 (4)
H1A	0.7167	0.7334	0.8091	0.067*
H1B	0.7367	0.5960	0.7006	0.067*
C2	0.9642 (2)	0.73491 (18)	0.78307 (15)	0.0501 (4)
C3	1.0607 (3)	0.8300 (2)	0.89533 (17)	0.0650 (5)
H3	1.0125	0.8475	0.9733	0.078*
C4	1.2266 (3)	0.8989 (2)	0.89318 (18)	0.0707 (5)
H4	1.2900	0.9625	0.9689	0.085*
C5	1.2976 (2)	0.8726 (2)	0.77783 (18)	0.0584 (5)
C6	1.2062 (2)	0.77923 (19)	0.66533 (16)	0.0563 (4)
H6	1.2553	0.7623	0.5878	0.068*
C7	1.0400 (2)	0.71053 (19)	0.66882 (16)	0.0546 (4)
H7	0.9778	0.6465	0.5928	0.066*
C8	0.78772 (19)	0.46120 (17)	0.86693 (15)	0.0462 (4)
C9	0.8332 (2)	0.36663 (18)	0.74715 (15)	0.0491 (4)
C10	0.9062 (3)	0.1503 (2)	0.65285 (18)	0.0641 (5)
H10A	1.0026	0.1973	0.6190	0.077*
H10B	0.8133	0.1060	0.5855	0.077*
C11	0.9509 (3)	0.0421 (2)	0.6971 (2)	0.0779 (6)
H11A	1.0399	0.0877	0.7659	0.117*
H11B	0.9883	−0.0249	0.6267	0.117*
H11C	0.8533	−0.0063	0.7270	0.117*
C12	0.7612 (2)	0.44406 (18)	0.98320 (15)	0.0479 (4)
H12	0.7698	0.3673	1.0054	0.058*
C13	0.71823 (19)	0.56638 (17)	1.06121 (15)	0.0457 (4)
C14	0.67851 (19)	0.60557 (18)	1.19642 (15)	0.0473 (4)
C15	0.6985 (2)	0.5232 (2)	1.26854 (16)	0.0564 (4)
H15	0.7340	0.4412	1.2303	0.068*
C16	0.6660 (3)	0.5621 (2)	1.39691 (18)	0.0656 (5)
H16	0.6798	0.5062	1.4441	0.079*
C17	0.6135 (3)	0.6829 (2)	1.45453 (18)	0.0676 (5)
H17	0.5926	0.7095	1.5408	0.081*
C18	0.5921 (2)	0.7646 (2)	1.38374 (19)	0.0678 (5)
H18	0.5561	0.8462	1.4226	0.081*
C19	0.6235 (2)	0.7266 (2)	1.25547 (17)	0.0573 (4)
H19	0.6077	0.7823	1.2086	0.069*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0670 (3)	0.0917 (4)	0.0892 (4)	0.0145 (3)	0.0093 (3)	0.0313 (3)
O1	0.0907 (10)	0.0682 (8)	0.0420 (7)	0.0261 (7)	0.0127 (6)	0.0173 (6)
O2	0.0781 (8)	0.0569 (7)	0.0473 (7)	0.0281 (6)	0.0168 (6)	0.0146 (6)
N1	0.0541 (8)	0.0561 (8)	0.0408 (7)	0.0195 (6)	0.0075 (6)	0.0175 (6)
N2	0.0560 (8)	0.0559 (8)	0.0444 (8)	0.0206 (7)	0.0092 (6)	0.0162 (7)
C1	0.0677 (11)	0.0640 (11)	0.0460 (9)	0.0263 (9)	0.0052 (8)	0.0247 (8)
C2	0.0668 (11)	0.0502 (9)	0.0394 (8)	0.0232 (8)	0.0059 (7)	0.0179 (7)
C3	0.0789 (13)	0.0709 (12)	0.0386 (9)	0.0173 (10)	0.0123 (9)	0.0126 (9)
C4	0.0802 (14)	0.0731 (13)	0.0436 (10)	0.0107 (11)	−0.0019 (9)	0.0078 (9)
C5	0.0652 (11)	0.0596 (11)	0.0548 (10)	0.0218 (9)	0.0074 (8)	0.0217 (9)
C6	0.0716 (12)	0.0619 (11)	0.0425 (9)	0.0280 (9)	0.0133 (8)	0.0199 (8)
C7	0.0735 (12)	0.0567 (10)	0.0353 (8)	0.0233 (9)	0.0027 (8)	0.0138 (7)
C8	0.0446 (8)	0.0502 (9)	0.0416 (8)	0.0130 (7)	0.0028 (7)	0.0129 (7)
C9	0.0480 (9)	0.0523 (10)	0.0413 (9)	0.0101 (7)	0.0031 (7)	0.0116 (7)
C10	0.0764 (13)	0.0584 (11)	0.0516 (10)	0.0247 (10)	0.0141 (9)	0.0070 (9)
C11	0.0853 (15)	0.0660 (13)	0.0883 (16)	0.0333 (11)	0.0253 (12)	0.0252 (12)
C12	0.0499 (9)	0.0502 (9)	0.0439 (9)	0.0142 (7)	0.0049 (7)	0.0158 (7)
C13	0.0419 (8)	0.0513 (9)	0.0419 (8)	0.0117 (7)	0.0034 (6)	0.0144 (7)
C14	0.0408 (8)	0.0534 (9)	0.0426 (9)	0.0100 (7)	0.0042 (6)	0.0121 (7)
C15	0.0632 (11)	0.0588 (10)	0.0461 (9)	0.0171 (9)	0.0082 (8)	0.0161 (8)
C16	0.0717 (12)	0.0778 (13)	0.0475 (10)	0.0166 (10)	0.0096 (9)	0.0242 (10)
C17	0.0681 (12)	0.0852 (14)	0.0425 (10)	0.0185 (10)	0.0140 (8)	0.0149 (10)
C18	0.0641 (12)	0.0720 (13)	0.0585 (11)	0.0247 (10)	0.0132 (9)	0.0070 (10)
C19	0.0573 (10)	0.0629 (11)	0.0513 (10)	0.0220 (9)	0.0094 (8)	0.0151 (9)

Geometric parameters (Å, º) top

Cl1—C5	1.750 (2)	C8—C9	1.469 (2)
O1—C9	1.207 (2)	C10—C11	1.490 (3)
O2—C9	1.331 (2)	C10—H10A	0.9700
O2—C10	1.452 (2)	C10—H10B	0.9700
N1—N2	1.3475 (19)	C11—H11A	0.9600
N1—C8	1.362 (2)	C11—H11B	0.9600
N1—C1	1.468 (2)	C11—H11C	0.9600
N2—C13	1.341 (2)	C12—C13	1.399 (2)
C1—C2	1.508 (3)	C12—H12	0.9300
C1—H1A	0.9700	C13—C14	1.473 (2)
C1—H1B	0.9700	C14—C19	1.389 (2)
C2—C7	1.384 (2)	C14—C15	1.392 (2)
C2—C3	1.389 (3)	C15—C16	1.387 (2)
C3—C4	1.377 (3)	C15—H15	0.9300
C3—H3	0.9300	C16—C17	1.374 (3)
C4—C5	1.375 (3)	C16—H16	0.9300
C4—H4	0.9300	C17—C18	1.377 (3)
C5—C6	1.370 (3)	C17—H17	0.9300
C6—C7	1.381 (3)	C18—C19	1.384 (3)
C6—H6	0.9300	C18—H18	0.9300
C7—H7	0.9300	C19—H19	0.9300
C8—C12	1.372 (2)

C9—O2—C10	115.81 (13)	O2—C10—H10A	110.3
N2—N1—C8	111.51 (13)	C11—C10—H10A	110.3
N2—N1—C1	118.60 (14)	O2—C10—H10B	110.3
C8—N1—C1	129.64 (14)	C11—C10—H10B	110.3
C13—N2—N1	105.49 (13)	H10A—C10—H10B	108.6
N1—C1—C2	112.37 (13)	C10—C11—H11A	109.5
N1—C1—H1A	109.1	C10—C11—H11B	109.5
C2—C1—H1A	109.1	H11A—C11—H11B	109.5
N1—C1—H1B	109.1	C10—C11—H11C	109.5
C2—C1—H1B	109.1	H11A—C11—H11C	109.5
H1A—C1—H1B	107.9	H11B—C11—H11C	109.5
C7—C2—C3	118.03 (17)	C8—C12—C13	105.44 (15)
C7—C2—C1	121.30 (16)	C8—C12—H12	127.3
C3—C2—C1	120.66 (15)	C13—C12—H12	127.3
C4—C3—C2	121.10 (17)	N2—C13—C12	110.70 (14)
C4—C3—H3	119.5	N2—C13—C14	120.36 (14)
C2—C3—H3	119.5	C12—C13—C14	128.93 (15)
C5—C4—C3	119.29 (18)	C19—C14—C15	118.53 (16)
C5—C4—H4	120.4	C19—C14—C13	120.92 (15)
C3—C4—H4	120.4	C15—C14—C13	120.54 (15)
C6—C5—C4	121.16 (18)	C16—C15—C14	120.64 (17)
C6—C5—Cl1	119.15 (14)	C16—C15—H15	119.7
C4—C5—Cl1	119.69 (15)	C14—C15—H15	119.7
C5—C6—C7	118.99 (16)	C17—C16—C15	120.21 (19)
C5—C6—H6	120.5	C17—C16—H16	119.9
C7—C6—H6	120.5	C15—C16—H16	119.9
C6—C7—C2	121.43 (16)	C16—C17—C18	119.58 (18)
C6—C7—H7	119.3	C16—C17—H17	120.2
C2—C7—H7	119.3	C18—C17—H17	120.2
N1—C8—C12	106.85 (14)	C17—C18—C19	120.77 (18)
N1—C8—C9	122.81 (14)	C17—C18—H18	119.6
C12—C8—C9	130.33 (15)	C19—C18—H18	119.6
O1—C9—O2	124.39 (15)	C18—C19—C14	120.25 (18)
O1—C9—C8	125.32 (16)	C18—C19—H19	119.9
O2—C9—C8	110.29 (14)	C14—C19—H19	119.9
O2—C10—C11	107.06 (16)

C8—N1—N2—C13	−0.84 (18)	C12—C8—C9—O1	176.62 (18)
C1—N1—N2—C13	−175.68 (14)	N1—C8—C9—O2	178.64 (14)
N2—N1—C1—C2	96.41 (17)	C12—C8—C9—O2	−3.3 (2)
C8—N1—C1—C2	−77.4 (2)	C9—O2—C10—C11	171.93 (16)
N1—C1—C2—C7	126.30 (17)	N1—C8—C12—C13	−0.64 (17)
N1—C1—C2—C3	−55.0 (2)	C9—C8—C12—C13	−178.92 (16)
C7—C2—C3—C4	0.4 (3)	N1—N2—C13—C12	0.41 (18)
C1—C2—C3—C4	−178.33 (18)	N1—N2—C13—C14	179.81 (13)
C2—C3—C4—C5	−0.1 (3)	C8—C12—C13—N2	0.15 (18)
C3—C4—C5—C6	−0.1 (3)	C8—C12—C13—C14	−179.18 (15)
C3—C4—C5—Cl1	179.85 (16)	N2—C13—C14—C19	6.6 (2)
C4—C5—C6—C7	−0.1 (3)	C12—C13—C14—C19	−174.15 (17)
Cl1—C5—C6—C7	179.98 (13)	N2—C13—C14—C15	−172.21 (15)
C5—C6—C7—C2	0.5 (3)	C12—C13—C14—C15	7.1 (3)
C3—C2—C7—C6	−0.6 (3)	C19—C14—C15—C16	−0.7 (3)
C1—C2—C7—C6	178.15 (15)	C13—C14—C15—C16	178.08 (16)
N2—N1—C8—C12	0.95 (18)	C14—C15—C16—C17	0.0 (3)
C1—N1—C8—C12	175.06 (16)	C15—C16—C17—C18	0.5 (3)
N2—N1—C8—C9	179.39 (14)	C16—C17—C18—C19	−0.3 (3)
C1—N1—C8—C9	−6.5 (3)	C17—C18—C19—C14	−0.5 (3)
C10—O2—C9—O1	1.1 (3)	C15—C14—C19—C18	1.0 (3)
C10—O2—C9—C8	−178.97 (14)	C13—C14—C19—C18	−177.83 (16)
N1—C8—C9—O1	−1.4 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O1ⁱ	0.93	2.56	3.281 (2)	135
C1—H1B···O1	0.97	2.42	2.921 (2)	111

Symmetry code: (i) −x+2, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₉H₁₇ClN₂O₂
M_r	340.80
Crystal system, space group	Triclinic, P1
Temperature (K)	298
a, b, c (Å)	8.1815 (10), 10.4039 (12), 11.0969 (13)
α, β, γ (°)	109.981 (2), 90.107 (2), 104.046 (2)
V (Å³)	857.43 (18)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.24
Crystal size (mm)	0.26 × 0.24 × 0.20

Data collection
Diffractometer	Bruker SMART CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2003)
T_min, T_max	0.941, 0.954
No. of measured, independent and observed [I > 2σ(I)] reflections	4495, 3008, 2554
R_int	0.023
(sin θ/λ)_max (Å⁻¹)	0.596

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.039, 0.107, 1.03
No. of reflections	3008
No. of parameters	218
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.25, −0.30

Computer programs: SMART (Bruker, 2005), SAINT (Bruker, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), XP in SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O1ⁱ	0.93	2.56	3.281 (2)	135.2
C1—H1B···O1	0.97	2.42	2.921 (2)	111.4

Symmetry code: (i) −x+2, −y+1, −z+1.

References

Bruker (2005). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Ge, Y.-Q., Dong, W.-L., Xia, Y., Wei, F. & Zhao, B.-X. (2007). Acta Cryst. E63, o1313–o1314. Web of Science CSD CrossRef IUCr Journals Google Scholar
Ge, Y. Q., Hao, B. Q., Duan, G. Y. & Wang, J. W. (2011). J. Lumin. 131, 1070–1076. Web of Science CrossRef CAS Google Scholar
Ge, Y. Q., Jia, J., Li, Y., Yin, L. & Wang, J. W. (2009). Heterocycles, 42, 197–206. Google Scholar
Sheldrick, G. M. (2003). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Xia, Y., Dong, Z. W., Zhao, B. X., Ge, X., Meng, N., Shin, D. S. & Miao, J. Y. (2007). Bioorg. Med. Chem. 15, 6893–6899. Web of Science CrossRef PubMed CAS Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 68| Part 3| March 2012| Page o877

doi:10.1107/S1600536812007428

Open

access