1-[5-(3,4-Dichlorophenyl)-3-(2-naphthyl)-4,5-dihydropyrazol-1-yl]ethanone

Lu, Z.-K.; Li, S.; Feng, Y.

doi:10.1107/S1600536808026858

organic compounds

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ISSN: 2056-9890

Volume 64| Part 9| September 2008| Page o1827

doi:10.1107/S1600536808026858

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1-[5-(3,4-Dichlorophenyl)-3-(2-naphthyl)-4,5-dihydropyrazol-1-yl]ethanone

Zhi-Ke Lu,^a ^* Shen Li ^a and Yan Feng ^b

^aForestry College, GuangXi University, Nanning 530005, People's Republic of China, and ^bChemistry Department, Guangxi Industrial Vocational Technical College, Nanning 530001, People's Republic of China
^*Correspondence e-mail: lukz1886@yahoo.com.cn

(Received 10 August 2008; accepted 20 August 2008; online 23 August 2008)

In the title compound, C₂₁H₁₆Cl₂N₂O, the central pyrazoline ring makes dihedral angles of 90.1 (3) and 7.8 (3)°, with the pendant benzene ring and naphthalene ring system, respectively. In the crystal structure, weak C—H⋯O interactions lead to chains of molecules.

Related literature

For related literature, see: Lu et al. (2006 ).

Experimental

Crystal data

C₂₁H₁₆Cl₂N₂O
M_r = 383.26
Triclinic, $[P \overline 1]$
a = 6.2154 (12) Å
b = 9.3505 (19) Å
c = 16.319 (3) Å
α = 97.42 (3)°
β = 99.07 (3)°
γ = 104.12 (3)°
V = 894.2 (3) Å³
Z = 2
Mo Kα radiation
μ = 0.38 mm⁻¹
T = 113 (2) K
0.22 × 0.20 × 0.12 mm

Data collection

Rigaku Saturn diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku, 2004 ) T_min = 0.922, T_max = 0.956
9131 measured reflections
3155 independent reflections
2709 reflections with I > 2σ(I)
R_int = 0.037

Refinement

R[F² > 2σ(F²)] = 0.033
wR(F²) = 0.090
S = 1.04
3155 reflections
236 parameters
H-atom parameters constrained
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.28 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	2.58	3.501 (2)	171
Symmetry code: (i) x-2, y-1, z.

Data collection: CrystalClear (Rigaku, 2004); 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 global, I. DOI: 10.1107/S1600536808026858/hb2778sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808026858/hb2778Isup2.hkl

checkCIF report

Comment top

The title compound, (I), (Fig. 1) was prepared and structurally characterized as part of our ongoing studies (Lu et al., 2006) of pyrazoline derivatives.

The pendant C14—C19 benzene ring and C1—C10 naphthalene ring make dihedral angles of 90.1 (3) and 7.8 (3)°, respectively, with the central N1/N2/C11/C12/C13 pyrazoline ring. The dihedral angle between the C14—C19 ring and the C1—C10 ring is 86.8 (3)°. The molecule of (I) is chiral: in the arbitrarily chosen asymmetric unit, C13 has R configuration, but crystal symmetry generates a racemic mixture. In the crystal of (I), molecules are linked by a weak C—H···O interaction (Table 1 and Fig. 2) into infinite chains.

Related literature top

For related literature, see: Lu et al. (2006).

Experimental top

A mixture of 1-(naphthalen-2-yl)-3-(3,4-dichlorophenyl)prop-2-en-1-one (5.0 mmol), hydrazine hydrate (25.0 mmol) and acetic acid (30 ml) was heated at reflux for 5 h, then poured onto crushed ice. The precipitate was separated by filtration, washed with petroleum ether, and crystallized from ethyl acetate-petroleum ether to obtain the title compound.

The title compound (40 mg) was dissolved in a mixture of ethyl acetate (10 ml) and petroleum ether (30 ml) and the solution was kept at room temperature for 8 d. Natural evaporation of the solution gave colourless slabs of (I) suitable for X-Ray analysis. M.p. 515–516 K.

Computing details top

Data collection: CrystalClear (Rigaku, 2004); cell refinement: CrystalClear (Rigaku, 2004); data reduction: CrystalClear (Rigaku, 2004); 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 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of (I), shown with 30% probability displacement ellipsoids (arbitrary spheres for H atoms).
	Fig. 2. Part of the crystal structure of (I) showing C—H···O interactions as dashed lines.

1-[5-(3,4-Dichlorophenyl)-3-(2-naphthyl)-4,5-dihydropyrazol-1-yl]ethanone top

Crystal data top

C₂₁H₁₆Cl₂N₂O	Z = 2
M_r = 383.26	F(000) = 396
Triclinic, P1	D_x = 1.423 Mg m⁻³
Hall symbol: -P 1	Melting point: 515-516 K K
a = 6.2154 (12) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.3505 (19) Å	Cell parameters from 2978 reflections
c = 16.319 (3) Å	θ = 2.3–27.5°
α = 97.42 (3)°	µ = 0.38 mm⁻¹
β = 99.07 (3)°	T = 113 K
γ = 104.12 (3)°	Slab, colourless
V = 894.2 (3) Å³	0.22 × 0.20 × 0.12 mm

Data collection top

Rigaku saturn diffractometer	3155 independent reflections
Radiation source: rotating anode	2709 reflections with I > 2σ(I)
Confocal monochromator	R_int = 0.037
ω scans	θ_max = 25.0°, θ_min = 2.3°
Absorption correction: multi-scan (CrystalClear; Rigaku, 2004)	h = −7→7
T_min = 0.922, T_max = 0.956	k = −11→10
9131 measured reflections	l = −18→19

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)] = 0.033	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.090	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0556P)² + 0.0148P] where P = (F_o² + 2F_c²)/3
3155 reflections	(Δ/σ)_max = 0.002
236 parameters	Δρ_max = 0.20 e Å⁻³
0 restraints	Δρ_min = −0.28 e Å⁻³

Crystal data top

C₂₁H₁₆Cl₂N₂O	γ = 104.12 (3)°
M_r = 383.26	V = 894.2 (3) Å³
Triclinic, P1	Z = 2
a = 6.2154 (12) Å	Mo Kα radiation
b = 9.3505 (19) Å	µ = 0.38 mm⁻¹
c = 16.319 (3) Å	T = 113 K
α = 97.42 (3)°	0.22 × 0.20 × 0.12 mm
β = 99.07 (3)°

Data collection top

Rigaku saturn diffractometer	3155 independent reflections
Absorption correction: multi-scan (CrystalClear; Rigaku, 2004)	2709 reflections with I > 2σ(I)
T_min = 0.922, T_max = 0.956	R_int = 0.037
9131 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.033	0 restraints
wR(F²) = 0.090	H-atom parameters constrained
S = 1.05	Δρ_max = 0.20 e Å⁻³
3155 reflections	Δρ_min = −0.28 e Å⁻³
236 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	1.32350 (7)	0.97267 (5)	1.10751 (3)	0.02660 (14)
Cl2	1.68608 (7)	0.78933 (5)	1.08859 (3)	0.02684 (14)
O1	1.53261 (19)	0.68503 (13)	0.74819 (7)	0.0286 (3)
N1	0.9532 (2)	0.50512 (15)	0.67138 (8)	0.0198 (3)
N2	1.1666 (2)	0.55742 (15)	0.72303 (8)	0.0206 (3)
C1	0.4859 (3)	0.37150 (18)	0.59400 (10)	0.0215 (4)
H1	0.5670	0.4456	0.5692	0.026*
C2	0.2643 (3)	0.30298 (19)	0.55983 (11)	0.0239 (4)
H2	0.1959	0.3315	0.5120	0.029*
C3	0.1354 (3)	0.18853 (18)	0.59586 (10)	0.0215 (4)
C4	−0.0965 (3)	0.11843 (19)	0.56347 (11)	0.0266 (4)
H4	−0.1698	0.1478	0.5170	0.032*
C5	−0.2152 (3)	0.0078 (2)	0.59938 (12)	0.0298 (4)
H5	−0.3681	−0.0362	0.5775	0.036*
C6	−0.1072 (3)	−0.03961 (19)	0.66921 (11)	0.0265 (4)
H6	−0.1882	−0.1154	0.6930	0.032*
C7	0.1177 (3)	0.02613 (19)	0.70205 (11)	0.0238 (4)
H7	0.1885	−0.0064	0.7478	0.029*
C8	0.2442 (3)	0.14301 (18)	0.66739 (10)	0.0195 (4)
C9	0.4748 (3)	0.21678 (18)	0.70202 (10)	0.0202 (4)
H9	0.5469	0.1879	0.7490	0.024*
C10	0.5944 (3)	0.33057 (17)	0.66748 (10)	0.0194 (4)
C11	0.8300 (3)	0.40644 (18)	0.70550 (10)	0.0185 (4)
C12	0.9545 (3)	0.37641 (18)	0.78625 (10)	0.0210 (4)
H12A	0.9740	0.2760	0.7790	0.025*
H12B	0.8751	0.3893	0.8321	0.025*
C13	1.1838 (3)	0.49564 (18)	0.80228 (10)	0.0205 (4)
H13	1.3077	0.4475	0.8076	0.025*
C14	1.2205 (3)	0.61660 (17)	0.87818 (10)	0.0188 (4)
C15	1.4098 (3)	0.64529 (18)	0.94150 (10)	0.0198 (4)
H15	1.5156	0.5910	0.9367	0.024*
C16	1.4433 (3)	0.75409 (18)	1.01202 (10)	0.0197 (4)
C17	1.2860 (3)	0.83565 (17)	1.01969 (10)	0.0204 (4)
C18	1.0972 (3)	0.80925 (19)	0.95591 (11)	0.0245 (4)
H18	0.9926	0.8645	0.9605	0.029*
C19	1.0647 (3)	0.70084 (19)	0.88558 (11)	0.0243 (4)
H19	0.9384	0.6838	0.8429	0.029*
C20	1.3468 (3)	0.64765 (18)	0.70068 (11)	0.0220 (4)
C21	1.3033 (3)	0.6979 (2)	0.61719 (11)	0.0283 (4)
H21A	1.2530	0.7871	0.6245	0.042*
H21B	1.1888	0.6204	0.5783	0.042*
H21C	1.4403	0.7182	0.5954	0.042*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0326 (3)	0.0253 (3)	0.0227 (2)	0.01150 (19)	0.00395 (18)	0.00158 (18)
Cl2	0.0236 (2)	0.0309 (3)	0.0231 (2)	0.00903 (19)	−0.00383 (17)	0.00134 (18)
O1	0.0188 (6)	0.0310 (7)	0.0312 (7)	−0.0007 (5)	0.0034 (5)	0.0045 (6)
N1	0.0164 (7)	0.0214 (7)	0.0185 (7)	0.0017 (6)	0.0020 (6)	0.0008 (6)
N2	0.0166 (7)	0.0245 (8)	0.0178 (7)	0.0005 (6)	0.0022 (6)	0.0046 (6)
C1	0.0215 (9)	0.0208 (9)	0.0212 (9)	0.0025 (7)	0.0054 (7)	0.0044 (7)
C2	0.0237 (9)	0.0251 (10)	0.0217 (9)	0.0047 (7)	0.0029 (7)	0.0052 (7)
C3	0.0204 (9)	0.0199 (9)	0.0222 (9)	0.0031 (7)	0.0054 (7)	−0.0006 (7)
C4	0.0210 (9)	0.0267 (10)	0.0282 (9)	0.0022 (7)	0.0017 (7)	0.0033 (8)
C5	0.0190 (9)	0.0273 (10)	0.0362 (11)	−0.0026 (8)	0.0040 (8)	−0.0001 (8)
C6	0.0260 (9)	0.0194 (9)	0.0307 (10)	−0.0022 (7)	0.0109 (8)	0.0023 (8)
C7	0.0263 (9)	0.0209 (9)	0.0228 (9)	0.0029 (7)	0.0064 (7)	0.0029 (7)
C8	0.0202 (8)	0.0172 (8)	0.0198 (8)	0.0029 (7)	0.0075 (7)	−0.0015 (7)
C9	0.0219 (9)	0.0194 (9)	0.0185 (8)	0.0043 (7)	0.0041 (7)	0.0024 (7)
C10	0.0189 (8)	0.0190 (9)	0.0194 (8)	0.0040 (7)	0.0056 (7)	0.0000 (7)
C11	0.0183 (8)	0.0176 (9)	0.0200 (8)	0.0051 (7)	0.0064 (7)	0.0018 (7)
C12	0.0201 (8)	0.0205 (9)	0.0202 (8)	0.0022 (7)	0.0021 (7)	0.0038 (7)
C13	0.0179 (8)	0.0237 (9)	0.0201 (8)	0.0046 (7)	0.0034 (7)	0.0066 (7)
C14	0.0177 (8)	0.0184 (9)	0.0202 (8)	0.0029 (7)	0.0045 (7)	0.0060 (7)
C15	0.0184 (8)	0.0211 (9)	0.0228 (9)	0.0074 (7)	0.0057 (7)	0.0079 (7)
C16	0.0181 (8)	0.0212 (9)	0.0183 (8)	0.0029 (7)	0.0007 (7)	0.0067 (7)
C17	0.0257 (9)	0.0171 (9)	0.0189 (8)	0.0049 (7)	0.0063 (7)	0.0042 (7)
C18	0.0230 (9)	0.0266 (10)	0.0274 (9)	0.0124 (8)	0.0054 (7)	0.0064 (8)
C19	0.0183 (8)	0.0288 (10)	0.0246 (9)	0.0064 (7)	−0.0001 (7)	0.0057 (8)
C20	0.0196 (9)	0.0190 (9)	0.0255 (9)	0.0023 (7)	0.0056 (7)	0.0014 (7)
C21	0.0261 (10)	0.0289 (10)	0.0283 (9)	0.0004 (8)	0.0090 (8)	0.0086 (8)

Geometric parameters (Å, º) top

Cl1—C17	1.7391 (17)	C9—C10	1.380 (2)
Cl2—C16	1.7329 (17)	C9—H9	0.9300
O1—C20	1.228 (2)	C10—C11	1.458 (2)
N1—C11	1.292 (2)	C11—C12	1.515 (2)
N1—N2	1.3905 (18)	C12—C13	1.541 (2)
N2—C20	1.359 (2)	C12—H12A	0.9700
N2—C13	1.482 (2)	C12—H12B	0.9700
C1—C2	1.361 (2)	C13—C14	1.513 (2)
C1—C10	1.424 (2)	C13—H13	0.9800
C1—H1	0.9300	C14—C15	1.384 (2)
C2—C3	1.423 (2)	C14—C19	1.399 (2)
C2—H2	0.9300	C15—C16	1.386 (2)
C3—C4	1.412 (2)	C15—H15	0.9300
C3—C8	1.422 (2)	C16—C17	1.390 (2)
C4—C5	1.370 (2)	C17—C18	1.389 (2)
C4—H4	0.9300	C18—C19	1.383 (2)
C5—C6	1.407 (2)	C18—H18	0.9300
C5—H5	0.9300	C19—H19	0.9300
C6—C7	1.370 (2)	C20—C21	1.504 (2)
C6—H6	0.9300	C21—H21A	0.9600
C7—C8	1.419 (2)	C21—H21B	0.9600
C7—H7	0.9300	C21—H21C	0.9600
C8—C9	1.418 (2)

C11—N1—N2	108.06 (13)	C11—C12—H12A	111.2
C20—N2—N1	123.49 (13)	C13—C12—H12A	111.2
C20—N2—C13	122.90 (14)	C11—C12—H12B	111.2
N1—N2—C13	113.44 (13)	C13—C12—H12B	111.2
C2—C1—C10	120.51 (16)	H12A—C12—H12B	109.1
C2—C1—H1	119.7	N2—C13—C14	111.22 (13)
C10—C1—H1	119.7	N2—C13—C12	101.19 (13)
C1—C2—C3	121.26 (16)	C14—C13—C12	114.05 (14)
C1—C2—H2	119.4	N2—C13—H13	110.0
C3—C2—H2	119.4	C14—C13—H13	110.0
C4—C3—C8	118.65 (15)	C12—C13—H13	110.0
C4—C3—C2	122.65 (16)	C15—C14—C19	119.04 (15)
C8—C3—C2	118.70 (15)	C15—C14—C13	120.14 (14)
C5—C4—C3	121.12 (17)	C19—C14—C13	120.82 (14)
C5—C4—H4	119.4	C14—C15—C16	120.68 (15)
C3—C4—H4	119.4	C14—C15—H15	119.7
C4—C5—C6	120.44 (16)	C16—C15—H15	119.7
C4—C5—H5	119.8	C15—C16—C17	120.00 (15)
C6—C5—H5	119.8	C15—C16—Cl2	119.11 (12)
C7—C6—C5	119.83 (16)	C17—C16—Cl2	120.87 (13)
C7—C6—H6	120.1	C18—C17—C16	119.75 (15)
C5—C6—H6	120.1	C18—C17—Cl1	119.24 (13)
C6—C7—C8	121.11 (16)	C16—C17—Cl1	121.01 (13)
C6—C7—H7	119.4	C19—C18—C17	120.04 (15)
C8—C7—H7	119.4	C19—C18—H18	120.0
C9—C8—C7	122.30 (16)	C17—C18—H18	120.0
C9—C8—C3	118.87 (15)	C18—C19—C14	120.47 (15)
C7—C8—C3	118.82 (15)	C18—C19—H19	119.8
C10—C9—C8	121.33 (15)	C14—C19—H19	119.8
C10—C9—H9	119.3	O1—C20—N2	119.98 (16)
C8—C9—H9	119.3	O1—C20—C21	123.45 (15)
C9—C10—C1	119.27 (15)	N2—C20—C21	116.56 (15)
C9—C10—C11	120.09 (15)	C20—C21—H21A	109.5
C1—C10—C11	120.64 (15)	C20—C21—H21B	109.5
N1—C11—C10	122.02 (15)	H21A—C21—H21B	109.5
N1—C11—C12	113.82 (14)	C20—C21—H21C	109.5
C10—C11—C12	124.16 (14)	H21A—C21—H21C	109.5
C11—C12—C13	102.71 (13)	H21B—C21—H21C	109.5

C11—N1—N2—C20	171.10 (14)	C10—C11—C12—C13	−174.36 (15)
C11—N1—N2—C13	−4.34 (17)	C20—N2—C13—C14	71.20 (19)
C10—C1—C2—C3	−0.4 (2)	N1—N2—C13—C14	−113.33 (15)
C1—C2—C3—C4	178.03 (16)	C20—N2—C13—C12	−167.31 (14)
C1—C2—C3—C8	−1.9 (2)	N1—N2—C13—C12	8.16 (16)
C8—C3—C4—C5	−0.5 (3)	C11—C12—C13—N2	−8.19 (14)
C2—C3—C4—C5	179.53 (16)	C11—C12—C13—C14	111.31 (15)
C3—C4—C5—C6	−0.7 (3)	N2—C13—C14—C15	−121.67 (16)
C4—C5—C6—C7	0.6 (3)	C12—C13—C14—C15	124.67 (16)
C5—C6—C7—C8	0.7 (3)	N2—C13—C14—C19	58.3 (2)
C6—C7—C8—C9	177.62 (15)	C12—C13—C14—C19	−55.3 (2)
C6—C7—C8—C3	−1.8 (2)	C19—C14—C15—C16	1.1 (2)
C4—C3—C8—C9	−177.73 (15)	C13—C14—C15—C16	−178.91 (14)
C2—C3—C8—C9	2.2 (2)	C14—C15—C16—C17	0.0 (2)
C4—C3—C8—C7	1.8 (2)	C14—C15—C16—Cl2	−178.49 (12)
C2—C3—C8—C7	−178.31 (15)	C15—C16—C17—C18	−1.0 (2)
C7—C8—C9—C10	−179.75 (15)	Cl2—C16—C17—C18	177.50 (13)
C3—C8—C9—C10	−0.3 (2)	C15—C16—C17—Cl1	179.93 (12)
C8—C9—C10—C1	−2.0 (2)	Cl2—C16—C17—Cl1	−1.6 (2)
C8—C9—C10—C11	178.74 (14)	C16—C17—C18—C19	0.8 (2)
C2—C1—C10—C9	2.3 (2)	Cl1—C17—C18—C19	179.94 (13)
C2—C1—C10—C11	−178.40 (15)	C17—C18—C19—C14	0.3 (3)
N2—N1—C11—C10	179.26 (13)	C15—C14—C19—C18	−1.2 (2)
N2—N1—C11—C12	−1.87 (18)	C13—C14—C19—C18	178.76 (14)
C9—C10—C11—N1	174.36 (14)	N1—N2—C20—O1	−177.25 (14)
C1—C10—C11—N1	−4.9 (2)	C13—N2—C20—O1	−2.2 (2)
C9—C10—C11—C12	−4.4 (2)	N1—N2—C20—C21	3.4 (2)
C1—C10—C11—C12	176.34 (14)	C13—N2—C20—C21	178.39 (14)
N1—C11—C12—C13	6.80 (17)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O1ⁱ	0.93	2.58	3.501 (2)	171

Symmetry code: (i) x−2, y−1, z.

Experimental details

Crystal data
Chemical formula	C₂₁H₁₆Cl₂N₂O
M_r	383.26
Crystal system, space group	Triclinic, P1
Temperature (K)	113
a, b, c (Å)	6.2154 (12), 9.3505 (19), 16.319 (3)
α, β, γ (°)	97.42 (3), 99.07 (3), 104.12 (3)
V (Å³)	894.2 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.38
Crystal size (mm)	0.22 × 0.20 × 0.12

Data collection
Diffractometer	Rigaku saturn diffractometer
Absorption correction	Multi-scan (CrystalClear; Rigaku, 2004)
T_min, T_max	0.922, 0.956
No. of measured, independent and observed [I > 2σ(I)] reflections	9131, 3155, 2709
R_int	0.037
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.033, 0.090, 1.05
No. of reflections	3155
No. of parameters	236
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.20, −0.28

Computer programs: CrystalClear (Rigaku, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), 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	2.58	3.501 (2)	171

Symmetry code: (i) x−2, y−1, z.

Acknowledgements

The authors thank Dr Haibin Song of Nankai University for helpful discussions, and the Science Foundation of GuangXi University for financial support (DD180021).

References

Lu, Z.-K., Li, S. & Huang, P.-M. (2006). Acta Cryst. E62, o5830–o5831. Web of Science CSD CrossRef IUCr Journals Google Scholar
Rigaku (2004). 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