[1-(4-Chloro­phen­yl)-5-hy­droxy-3-phenyl-1H-pyrazol-4-yl](thio­phen-2-yl)methanone

Deng, G.-M.; Zhang, H.-M.; Ou-Yang, L.-Q.; Tong, Q.-Z.; Li, S.

doi:10.1107/S1600536812019253

organic compounds

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ISSN: 2056-9890

Volume 68| Part 6| June 2012| Page o1639

doi:10.1107/S1600536812019253

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[1-(4-Chlorophenyl)-5-hydroxy-3-phenyl-1H-pyrazol-4-yl](thiophen-2-yl)methanone

Gui-Ming Deng,^a,^b He-Ming Zhang,^a ^* Lin-Qi Ou-Yang,^b Qiao-Zhen Tong ^b and Shan Li ^b

^aMOE Key Laboratory of Laser Life Science & Institute of Laser Life Science, College of Biophotonics, South China Normal University, Guangzhou 510631, People's Republic of China, and ^bThe First Affiliated Hospital of Hunan University of Chinese Medicine, Changsha 410007, People's Republic of China
^*Correspondence e-mail: zhang_heming88@yahoo.com.cn

(Received 27 April 2012; accepted 29 April 2012; online 5 May 2012)

In the title compound, C₂₀H₁₃ClN₂O₂S, the chlorophenyl, phenyl and thienoyl rings are oriented at dihedral angles 17.84 (7), 53.13 (8) and 34.03 (8)°, respectively, to the central pyrazole ring. An intramolecular O—H⋯O hydrogen bond occurs. In the crystal, pairs of bifurcated O—H⋯O hydrogen bonds link molecules into inversion dimers with R₂²(12) graph-set motifs.

Related literature

For general background to pyrazolone and its complexes, see: Li et al. (2000 ); Kimata et al. (2007 ). For related structures, see: Li et al. (2007 ); Cingolani et al. (2004 ); Holzer et al. (1999 ). For the synthesis of the title compound, see: Jensen (1959 ). For bond-length data, see: Allen et al. (1987 ); Foces-Foces et al. (1997 ). For graph-set motifs, see: Etter et al. (1990 ).

Experimental

Crystal data

C₂₀H₁₃ClN₂O₂S
M_r = 380.84
Monoclinic, P 2₁ /c
a = 6.0686 (2) Å
b = 18.6887 (5) Å
c = 14.9734 (4) Å
β = 91.559 (1)°
V = 1697.57 (9) Å³
Z = 4
Mo Kα radiation
μ = 0.37 mm⁻¹
T = 296 K
0.22 × 0.20 × 0.18 mm

Data collection

Bruker SMART CCD diffractometer
20900 measured reflections
3351 independent reflections
3072 reflections with I > 2σ(I)
R_int = 0.024

Refinement

R[F² > 2σ(F²)] = 0.031
wR(F²) = 0.088
S = 1.06
3351 reflections
235 parameters
H-atom parameters constrained
Δρ_max = 0.31 e Å⁻³
Δρ_min = −0.31 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O2	0.82	2.08	2.7233 (15)	135
O1—H1⋯O2ⁱ	0.82	2.12	2.7964 (15)	140
Symmetry code: (i) -x, -y+1, -z+2.

Data collection: SMART (Bruker, 1998 ); cell refinement: SAINT (Bruker, 1998); 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/S1600536812019253/xu5526sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812019253/xu5526Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812019253/xu5526Isup3.cml

checkCIF report

Comment top

Pyrazolone, as a prominent structural motif, is found in numerous active compounds. Due to the easy preparation and its rich biological activity of broad-spectrum antibacterial action, antitumor, antisepsis(Kimata et al., 2007). Pyrazolone and its complexes have both received considerable attention in coordination chemistry and medicinal chemistry(Li et al., 2000).We report here the crystal structure of a new 4-heterocyclic acylpyrazolone (Fig. 1).

The chlorophenyl ring is slightly twisted by 17.84 (1) with respect to the pyrazolone ring, whereas the benzene and 2-thienoyl rings make dihedral angles of 53.13 (3) and 34.03 (1), respectively, with the pyrazolone (Fig. 1). The clear evidence of the hydroxyl H atom in the difference Fourier synthesis and the absence of any residual electron density in the vicinity of C7 confirm that compound (I) crystallizes as a pure enol tautomer and that no desmotropism is present (Foces-Foces et al., 1997).

The molecular structure of (I) is shown in Fig. 1, and the intermolecular O—H···O hydrogen bond (Table 1) results in the formation of a dimer with an R₂²(12) graph-set motif(Etter et al., 1990)(Fig. 2.). The bond lengths and angles are within normal ranges (Allen et al., 1987). Similar crystal structure of some compounds have been reported (Li et al., 2007; Cingolani et al., 2004; Holzer et al.., 1999).

Related literature top

For general background to pyrazolone and its complexes, see: Li et al. (2000); Kimata et al. (2007). For related structures, see: Li et al. (2007); Cingolani et al. (2004); Holzer et al. (1999). For the synthesis of the title compound, see: Jensen (1959). For bond-length data, see: Allen et al. (1987); Foces-Foces et al. (1997). For graph-set motifs, see: Etter et al. (1990).

Experimental top

Compound (I) was synthesized and purified according to the method proposed by Jensen (1959). (yield 72.4%.). Analysis, required for C₂₀H₁₃ClN₂O₂S: C 63.07, H 3.44, N 9.31%, S 8.42; found: C 63.01, H 3.53, N 9.34%, S 8.47. Block-like yellow single crystals of (I) were grown from an ethanol solution by slow evaporation for several weeks.

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT (Bruker, 1998); 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. The molecular structure of (I) (thermal ellipsoids are shown at 30% probability levels).
	Fig. 2. The structure of a dimer of (I).

[1-(4-Chlorophenyl)-5-hydroxy-3-phenyl-1H-pyrazol-4-yl](thiophen- 2-yl)methanone top

Crystal data top

C₂₀H₁₃ClN₂O₂S	F(000) = 784.0
M_r = 380.84	D_x = 1.490 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 9988 reflections
a = 6.0686 (2) Å	θ = 3.1–28.2°
b = 18.6887 (5) Å	µ = 0.37 mm⁻¹
c = 14.9734 (4) Å	T = 296 K
β = 91.559 (1)°	Block, yellow
V = 1697.57 (9) Å³	0.22 × 0.20 × 0.18 mm
Z = 4

Data collection top

Bruker SMART CCD diffractometer	3072 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.024
Graphite monochromator	θ_max = 26.0°, θ_min = 1.7°
ω scans	h = −7→7
20900 measured reflections	k = −23→22
3351 independent reflections	l = −18→18

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)] = 0.031	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.088	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.0494P)² + 0.8P] where P = (F_o² + 2F_c²)/3
3351 reflections	(Δ/σ)_max = 0.002
235 parameters	Δρ_max = 0.31 e Å⁻³
0 restraints	Δρ_min = −0.31 e Å⁻³

Crystal data top

C₂₀H₁₃ClN₂O₂S	V = 1697.57 (9) Å³
M_r = 380.84	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 6.0686 (2) Å	µ = 0.37 mm⁻¹
b = 18.6887 (5) Å	T = 296 K
c = 14.9734 (4) Å	0.22 × 0.20 × 0.18 mm
β = 91.559 (1)°

Data collection top

Bruker SMART CCD diffractometer	3072 reflections with I > 2σ(I)
20900 measured reflections	R_int = 0.024
3351 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.031	0 restraints
wR(F²) = 0.088	H-atom parameters constrained
S = 1.06	Δρ_max = 0.31 e Å⁻³
3351 reflections	Δρ_min = −0.31 e Å⁻³
235 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	0.7121 (2)	0.56022 (8)	0.81785 (9)	0.0221 (3)
C2	0.6399 (2)	0.49761 (8)	0.77634 (10)	0.0261 (3)
H2	0.5030	0.4784	0.7892	0.031*
C3	0.7742 (3)	0.46391 (8)	0.71551 (10)	0.0269 (3)
H3	0.7280	0.4219	0.6876	0.032*
C4	0.9765 (2)	0.49323 (8)	0.69683 (10)	0.0241 (3)
C5	1.0483 (2)	0.55577 (8)	0.73728 (10)	0.0258 (3)
H5	1.1843	0.5752	0.7235	0.031*
C6	0.9166 (2)	0.58925 (8)	0.79828 (10)	0.0255 (3)
H6	0.9643	0.6311	0.8263	0.031*
C7	0.4045 (2)	0.57557 (8)	0.92592 (9)	0.0224 (3)
C8	0.3346 (2)	0.63263 (8)	0.97842 (9)	0.0222 (3)
C9	0.4825 (2)	0.68917 (8)	0.95717 (9)	0.0223 (3)
C10	0.4907 (2)	0.76450 (8)	0.98822 (9)	0.0218 (3)
C11	0.3064 (2)	0.80840 (8)	0.98391 (10)	0.0252 (3)
H11	0.1744	0.7912	0.9594	0.030*
C12	0.3185 (3)	0.87803 (8)	1.01608 (11)	0.0301 (3)
H12	0.1949	0.9074	1.0125	0.036*
C13	0.5140 (3)	0.90380 (8)	1.05335 (11)	0.0311 (3)
H13	0.5209	0.9501	1.0760	0.037*
C14	0.6989 (3)	0.86062 (9)	1.05681 (10)	0.0301 (3)
H14	0.8305	0.8779	1.0817	0.036*
C15	0.6887 (2)	0.79162 (8)	1.02331 (10)	0.0257 (3)
H15	0.8146	0.7632	1.0242	0.031*
C16	0.1539 (2)	0.62147 (8)	1.03925 (10)	0.0236 (3)
C17	0.1226 (2)	0.66529 (8)	1.11888 (10)	0.0234 (3)
C18	0.2674 (3)	0.71042 (8)	1.16592 (10)	0.0281 (3)
H18	0.4099	0.7209	1.1487	0.034*
C19	0.1698 (3)	0.73824 (9)	1.24312 (11)	0.0363 (4)
H19	0.2418	0.7694	1.2826	0.044*
C20	−0.0405 (3)	0.71486 (9)	1.25382 (11)	0.0367 (4)
H20	−0.1283	0.7290	1.3006	0.044*
Cl1	1.14533 (6)	0.45042 (2)	0.62109 (2)	0.03082 (12)
N1	0.5794 (2)	0.59767 (6)	0.87952 (8)	0.0233 (3)
N2	0.6279 (2)	0.66882 (6)	0.89840 (8)	0.0246 (3)
O1	0.33334 (17)	0.50886 (5)	0.91919 (7)	0.0258 (2)
H1	0.2308	0.5029	0.9530	0.039*
O2	0.02678 (19)	0.57078 (6)	1.02388 (8)	0.0355 (3)
S1	−0.12432 (6)	0.65709 (2)	1.17238 (3)	0.03080 (12)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0219 (7)	0.0224 (7)	0.0221 (7)	0.0033 (5)	0.0034 (5)	0.0018 (5)
C2	0.0230 (7)	0.0248 (7)	0.0308 (7)	−0.0007 (6)	0.0056 (6)	0.0006 (6)
C3	0.0303 (8)	0.0222 (7)	0.0283 (7)	0.0008 (6)	0.0039 (6)	−0.0027 (6)
C4	0.0258 (7)	0.0246 (7)	0.0221 (7)	0.0063 (6)	0.0047 (5)	0.0018 (5)
C5	0.0215 (7)	0.0282 (8)	0.0278 (7)	−0.0003 (6)	0.0049 (6)	0.0009 (6)
C6	0.0250 (7)	0.0242 (7)	0.0275 (7)	−0.0010 (6)	0.0029 (6)	−0.0013 (6)
C7	0.0215 (7)	0.0225 (7)	0.0233 (7)	−0.0011 (5)	0.0020 (5)	0.0015 (5)
C8	0.0214 (7)	0.0228 (7)	0.0226 (7)	0.0006 (5)	0.0027 (5)	0.0007 (5)
C9	0.0215 (7)	0.0209 (7)	0.0245 (7)	0.0012 (5)	0.0022 (5)	0.0021 (5)
C10	0.0241 (7)	0.0210 (7)	0.0206 (6)	−0.0004 (5)	0.0056 (5)	0.0024 (5)
C11	0.0222 (7)	0.0281 (8)	0.0254 (7)	0.0006 (6)	0.0009 (6)	−0.0005 (6)
C12	0.0309 (8)	0.0263 (8)	0.0335 (8)	0.0065 (6)	0.0054 (6)	−0.0001 (6)
C13	0.0410 (9)	0.0233 (7)	0.0293 (8)	−0.0034 (7)	0.0074 (7)	−0.0042 (6)
C14	0.0288 (8)	0.0323 (8)	0.0291 (8)	−0.0094 (6)	0.0004 (6)	0.0010 (6)
C15	0.0218 (7)	0.0263 (7)	0.0290 (7)	0.0005 (6)	0.0028 (6)	0.0054 (6)
C16	0.0221 (7)	0.0232 (7)	0.0257 (7)	0.0011 (6)	0.0038 (6)	0.0031 (6)
C17	0.0222 (7)	0.0240 (7)	0.0242 (7)	0.0038 (5)	0.0052 (6)	0.0049 (6)
C18	0.0340 (8)	0.0273 (7)	0.0231 (7)	0.0026 (6)	0.0070 (6)	0.0042 (6)
C19	0.0485 (10)	0.0318 (8)	0.0288 (8)	−0.0009 (7)	0.0050 (7)	−0.0022 (7)
C20	0.0466 (10)	0.0346 (9)	0.0297 (8)	0.0092 (7)	0.0148 (7)	0.0006 (7)
Cl1	0.0322 (2)	0.0302 (2)	0.0306 (2)	0.00225 (15)	0.01222 (15)	−0.00420 (14)
N1	0.0238 (6)	0.0194 (6)	0.0269 (6)	−0.0005 (5)	0.0062 (5)	−0.0010 (5)
N2	0.0248 (6)	0.0197 (6)	0.0298 (6)	−0.0007 (5)	0.0069 (5)	−0.0011 (5)
O1	0.0246 (5)	0.0227 (5)	0.0305 (5)	−0.0047 (4)	0.0081 (4)	−0.0014 (4)
O2	0.0344 (6)	0.0343 (6)	0.0386 (6)	−0.0122 (5)	0.0144 (5)	−0.0069 (5)
S1	0.0272 (2)	0.0344 (2)	0.0313 (2)	0.00437 (15)	0.01022 (16)	0.00459 (15)

Geometric parameters (Å, º) top

C1—C2	1.390 (2)	C11—C12	1.389 (2)
C1—C6	1.393 (2)	C11—H11	0.9300
C1—N1	1.4254 (18)	C12—C13	1.384 (2)
C2—C3	1.389 (2)	C12—H12	0.9300
C2—H2	0.9300	C13—C14	1.382 (2)
C3—C4	1.380 (2)	C13—H13	0.9300
C3—H3	0.9300	C14—C15	1.384 (2)
C4—C5	1.381 (2)	C14—H14	0.9300
C4—Cl1	1.7432 (14)	C15—H15	0.9300
C5—C6	1.380 (2)	C16—O2	1.2393 (19)
C5—H5	0.9300	C16—C17	1.463 (2)
C6—H6	0.9300	C17—C18	1.395 (2)
C7—O1	1.3224 (17)	C17—S1	1.7253 (14)
C7—N1	1.3491 (18)	C18—C19	1.412 (2)
C7—C8	1.397 (2)	C18—H18	0.9300
C8—C9	1.428 (2)	C19—C20	1.363 (3)
C8—C16	1.4595 (19)	C19—H19	0.9300
C9—N2	1.3191 (19)	C20—S1	1.6965 (19)
C9—C10	1.483 (2)	C20—H20	0.9300
C10—C11	1.387 (2)	N1—N2	1.3892 (17)
C10—C15	1.394 (2)	O1—H1	0.8200

C2—C1—C6	120.36 (13)	C13—C12—C11	120.18 (14)
C2—C1—N1	121.76 (13)	C13—C12—H12	119.9
C6—C1—N1	117.86 (13)	C11—C12—H12	119.9
C3—C2—C1	119.44 (14)	C14—C13—C12	119.87 (15)
C3—C2—H2	120.3	C14—C13—H13	120.1
C1—C2—H2	120.3	C12—C13—H13	120.1
C4—C3—C2	119.59 (14)	C13—C14—C15	120.14 (14)
C4—C3—H3	120.2	C13—C14—H14	119.9
C2—C3—H3	120.2	C15—C14—H14	119.9
C3—C4—C5	121.24 (14)	C14—C15—C10	120.32 (14)
C3—C4—Cl1	119.44 (12)	C14—C15—H15	119.8
C5—C4—Cl1	119.33 (11)	C10—C15—H15	119.8
C6—C5—C4	119.52 (14)	O2—C16—C8	117.89 (13)
C6—C5—H5	120.2	O2—C16—C17	119.04 (13)
C4—C5—H5	120.2	C8—C16—C17	123.02 (13)
C5—C6—C1	119.86 (14)	C18—C17—C16	131.02 (13)
C5—C6—H6	120.1	C18—C17—S1	111.24 (11)
C1—C6—H6	120.1	C16—C17—S1	117.53 (11)
O1—C7—N1	120.61 (13)	C17—C18—C19	111.34 (15)
O1—C7—C8	131.21 (13)	C17—C18—H18	124.3
N1—C7—C8	108.13 (12)	C19—C18—H18	124.3
C7—C8—C9	103.72 (12)	C20—C19—C18	113.14 (16)
C7—C8—C16	119.13 (13)	C20—C19—H19	123.4
C9—C8—C16	137.08 (13)	C18—C19—H19	123.4
N2—C9—C8	111.79 (13)	C19—C20—S1	112.52 (13)
N2—C9—C10	117.74 (13)	C19—C20—H20	123.7
C8—C9—C10	130.44 (13)	S1—C20—H20	123.7
C11—C10—C15	119.22 (14)	C7—N1—N2	110.71 (11)
C11—C10—C9	121.78 (13)	C7—N1—C1	130.51 (12)
C15—C10—C9	119.00 (13)	N2—N1—C1	118.78 (11)
C10—C11—C12	120.21 (14)	C9—N2—N1	105.65 (11)
C10—C11—H11	119.9	C7—O1—H1	109.5
C12—C11—H11	119.9	C20—S1—C17	91.72 (8)

C6—C1—C2—C3	0.4 (2)	C9—C10—C15—C14	−176.86 (13)
N1—C1—C2—C3	178.83 (13)	C7—C8—C16—O2	−21.5 (2)
C1—C2—C3—C4	−0.3 (2)	C9—C8—C16—O2	162.36 (17)
C2—C3—C4—C5	−0.2 (2)	C7—C8—C16—C17	155.84 (14)
C2—C3—C4—Cl1	179.53 (12)	C9—C8—C16—C17	−20.3 (3)
C3—C4—C5—C6	0.7 (2)	O2—C16—C17—C18	159.46 (16)
Cl1—C4—C5—C6	−179.03 (12)	C8—C16—C17—C18	−17.8 (2)
C4—C5—C6—C1	−0.6 (2)	O2—C16—C17—S1	−14.63 (19)
C2—C1—C6—C5	0.1 (2)	C8—C16—C17—S1	168.10 (11)
N1—C1—C6—C5	−178.40 (13)	C16—C17—C18—C19	−175.79 (15)
O1—C7—C8—C9	178.08 (15)	S1—C17—C18—C19	−1.42 (17)
N1—C7—C8—C9	0.69 (16)	C17—C18—C19—C20	0.0 (2)
O1—C7—C8—C16	0.8 (2)	C18—C19—C20—S1	1.4 (2)
N1—C7—C8—C16	−176.63 (12)	O1—C7—N1—N2	−178.57 (12)
C7—C8—C9—N2	−0.31 (17)	C8—C7—N1—N2	−0.85 (16)
C16—C8—C9—N2	176.25 (16)	O1—C7—N1—C1	1.4 (2)
C7—C8—C9—C10	177.61 (14)	C8—C7—N1—C1	179.14 (14)
C16—C8—C9—C10	−5.8 (3)	C2—C1—N1—C7	18.8 (2)
N2—C9—C10—C11	126.50 (15)	C6—C1—N1—C7	−162.77 (14)
C8—C9—C10—C11	−51.3 (2)	C2—C1—N1—N2	−161.23 (13)
N2—C9—C10—C15	−54.02 (19)	C6—C1—N1—N2	17.22 (19)
C8—C9—C10—C15	128.16 (17)	C8—C9—N2—N1	−0.18 (16)
C15—C10—C11—C12	−1.4 (2)	C10—C9—N2—N1	−178.39 (12)
C9—C10—C11—C12	178.06 (13)	C7—N1—N2—C9	0.64 (16)
C10—C11—C12—C13	−0.6 (2)	C1—N1—N2—C9	−179.36 (12)
C11—C12—C13—C14	1.4 (2)	C19—C20—S1—C17	−1.85 (14)
C12—C13—C14—C15	−0.2 (2)	C18—C17—S1—C20	1.86 (12)
C13—C14—C15—C10	−1.8 (2)	C16—C17—S1—C20	177.08 (12)
C11—C10—C15—C14	2.6 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2	0.82	2.08	2.7233 (15)	135
O1—H1···O2ⁱ	0.82	2.12	2.7964 (15)	140

Symmetry code: (i) −x, −y+1, −z+2.

Experimental details

Crystal data
Chemical formula	C₂₀H₁₃ClN₂O₂S
M_r	380.84
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	6.0686 (2), 18.6887 (5), 14.9734 (4)
β (°)	91.559 (1)
V (Å³)	1697.57 (9)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.37
Crystal size (mm)	0.22 × 0.20 × 0.18

Data collection
Diffractometer	Bruker SMART CCD diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	20900, 3351, 3072
R_int	0.024
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.031, 0.088, 1.06
No. of reflections	3351
No. of parameters	235
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.31, −0.31

Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1998), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2	0.82	2.08	2.7233 (15)	134.6
O1—H1···O2ⁱ	0.82	2.12	2.7964 (15)	139.9

Symmetry code: (i) −x, −y+1, −z+2.

Acknowledgements

This work was supported by the National Natural Science Foundation of China (30940094) and the Science Foundation for Excellent Youth Scholars of Educational Commission of Hunan Province, China (10B077).

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. CrossRef Web of Science Google Scholar
Bruker (1998). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Cingolani, A., Marchetti, F., Pettinari, C., Pettinari, R., Skelton, B. W. & White, A. H. (2004). Inorg. Chem. Commun. 7, 235–237. Web of Science CSD CrossRef CAS Google Scholar
Etter, M. C., MacDonald, J. C. & Bernstein, J. (1990). Acta Cryst. B46, 256–262. CrossRef CAS Web of Science IUCr Journals Google Scholar
Foces-Foces, C., Fontenas, C., Elguero, J. & Sobrados, I. (1997). An. Quim. Int. Ed. 93, 219–224. Google Scholar
Holzer, W., Mereiter, K. & Plagens, B. (1999). Heterocycles, 50, 799–818. CrossRef CAS Google Scholar
Jensen, B. S. (1959). Acta Chem. Scand. 13, 1668–1670. CrossRef CAS Web of Science Google Scholar
Kimata, A., Nakagawa, H., Ohyama, R., Fukuuchi, T., Ohta, S., Suzuki, T. & Miyata, N. (2007). J. Med. Chem. 50, 5053–5056. Web of Science CrossRef PubMed CAS Google Scholar
Li, J. Z., Li, G. & Yu, W. J. (2000). J. Rare Earths, 18, 233–236. Google Scholar
Li, J.-Z., Zhang, H.-Q., Li, H.-X., Che, P.-Z. & Wang, T.-C. (2007). Acta Cryst. E63, o1289–o1290. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 68| Part 6| June 2012| Page o1639

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