9-(2,4-Dichloro­phen­yl)-3,3,6,6-tetra­methyl-3,4,5,6-tetra­hydro-9H-xanthene-1,8(2H,7H)-dione

Shi, H.

doi:10.1107/S1600536810046702

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 66| Part 12| December 2010| Page o3200

https://doi.org/10.1107/S1600536810046702

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9-(2,4-Dichlorophenyl)-3,3,6,6-tetramethyl-3,4,5,6-tetrahydro-9H-xanthene-1,8(2H,7H)-dione

Hao Shi ^a ^*

^aThe College of Pharmaceutical Science, Zhejiang University of Technology, Hangzhou 310014, People's Republic of China
^*Correspondence e-mail: shihao@zjut.edu.cn

(Received 7 November 2010; accepted 11 November 2010; online 17 November 2010)

The title compound, C₂₃H₂₄Cl₂O₃, was synthesized by reaction of 2,4-dichlorobenzaldehyde and 5,5-dimethylcyclohexane-1,3-dione in ethylene glycol. The central ring of the xanthene moiety is almost planar (with an r.m.s. deviation of 0.0268 Å from the least-squares plane) while the two outer rings, in a cis arrangement, display envelope conformations. The ring of the 2,4-dichlorophenyl substituent is nearly perpendicular [85.89 (4)°] to the xanthene ring system.

Related literature

For related structures, see: Odabaşoğlu et al. (2008 ); Bigdeli et al. (2007 ); Tu et al. (2002 , 2004 ); Jeyakanthan et al. (1999 ); Li et al. (2005 ); Shi et al. (1997 ). For applications of xanthene derivatives, see: Poupelin et al. (1978 ); Lambert et al. (1997 ); Menchen et al. (2003 ); Banerjee & Mukherjee (1981 ). For ring puckering parameters, see: Cremer & Pople (1975 ).

Experimental

Crystal data

C₂₃H₂₄Cl₂O₃
M_r = 419.32
Monoclinic, P 2₁ /c
a = 9.8154 (10) Å
b = 19.833 (2) Å
c = 11.4441 (11) Å
β = 111.873 (2)°
V = 2067.4 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.34 mm⁻¹
T = 296 K
0.20 × 0.10 × 0.10 mm

Data collection

Bruker APEX CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 1997 ) T_min = 0.936, T_max = 0.967
13137 measured reflections
4961 independent reflections
3331 reflections with I > 2σ(I)
R_int = 0.027

Refinement

R[F² > 2σ(F²)] = 0.045
wR(F²) = 0.124
S = 1.02
4961 reflections
257 parameters
H-atom parameters constrained
Δρ_max = 0.36 e Å⁻³
Δρ_min = −0.55 e Å⁻³

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997 ); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536810046702/dn2622sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810046702/dn2622Isup2.hkl

checkCIF report

Comment top

Xanthene-based compounds are biological importance and useful in drug discovery, such as anti-inflammatory effect (Poupelin et al., 1978) and antiviral activity (Lambert et al., 1997). Xanthenes are also an important class of organic compounds that find uses as dyes and fluorescent materials for visualization of bio-molecules and laser technologies due to their useful spectroscopic properties (Menchen et al., 2003; Banerjee & Mukherjee, 1981). In view of the importance of the title compound, herein its crystal structure is reported.

The bond lengths and angles in the title molecule (Fig. 1) are comparable with those reported for related structures (Odabaşoğlu et al., 2008; Bigdeli et al., 2007; Tu et al., 2002; Jeyakanthan et al., 1999; Li et al., 2005; Shi et al., 1997; Tu et al., 2004). The central pyran ring of the xanthene moiety is planar, and the two outer rings (ring A (C1—C4/C11/C10) and ring C (C5–C8/C13/C12)) are in envelope conformations, ring A with puckering parameters (Cremer & Pople, 1975) Q= 0.4511 (22) Å, θ= 125.45 (27)°, φ = 297.4 (3)° and ring C with puckering parameters Q= 0.4807 (22) Å, θ= 56.96 (25)°, φ = 58.0 (3)°. Rings A and C are in a cis conformation, atoms C3 and C6 displaced by 0.6311 (28) and 0.6684 (28) Å from the plane of the other ring atoms, respectively. Ring D (C18—C23) is, of course, planar. The dihedral angle between the least-squares plane of the xanthene ring and the benzene ring is 85.89 (4)°.

Related literature top

For related structures, see: Odabaşoğlu et al. (2008); Bigdeli et al. (2007); Tu et al. (2002, 2004); Jeyakanthan et al. (1999); Li et al. (2005); Shi et al. (1997). For applications of xanthene derivatives, see: Poupelin et al. (1978); Lambert et al. (1997); Menchen et al. (2003); Banerjee & Mukherjee (1981). For ring puckering parameters, see: Cremer & Pople (1975).

Experimental top

A mixture of 2,4-dichlorobenzaldehyde (5 mmol), 5,5-dimethyl-1,3- cyclohexanedione (10 mmol) and 15 ml of ethylene glycol was transferred into a flask connected with refluxing equipment. After stirring at 80°C for 1.5 h, the reaction mixture was cooled to room temperature and poured into 150 ml water, the precipitated product was filtered and recrystallized with ethanol to give the title compound. Crystals suitable for X-ray structure analysis were obtained by slow evaporation from a solution of methanol at room temperature.

Structure description top

For related structures, see: Odabaşoğlu et al. (2008); Bigdeli et al. (2007); Tu et al. (2002, 2004); Jeyakanthan et al. (1999); Li et al. (2005); Shi et al. (1997). For applications of xanthene derivatives, see: Poupelin et al. (1978); Lambert et al. (1997); Menchen et al. (2003); Banerjee & Mukherjee (1981). For ring puckering parameters, see: Cremer & Pople (1975).

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The preparation of the title compound.
	Fig. 2. Structure of the title compound, showing 30% probability displacement ellipsoids with atomic numbering scheme.

9-(2,4-Dichlorophenyl)-3,3,6,6-tetramethyl-3,4,5,6-tetrahydro-9H- xanthene-1,8(2H,7H)-dione top

Crystal data top

C₂₃H₂₄Cl₂O₃	F(000) = 880
M_r = 419.32	D_x = 1.347 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3489 reflections
a = 9.8154 (10) Å	θ = 2.2–27.1°
b = 19.833 (2) Å	µ = 0.34 mm⁻¹
c = 11.4441 (11) Å	T = 296 K
β = 111.873 (2)°	Prism, colorless
V = 2067.4 (4) Å³	0.20 × 0.10 × 0.10 mm
Z = 4

Data collection top

Bruker APEX CCD diffractometer	4961 independent reflections
Radiation source: fine-focus sealed tube	3331 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.027
ω scans	θ_max = 28.2°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 1997)	h = −13→11
T_min = 0.936, T_max = 0.967	k = −25→26
13137 measured reflections	l = −13→14

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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.124	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0573P)² + 0.4531P] where P = (F_o² + 2F_c²)/3
4961 reflections	(Δ/σ)_max < 0.001
257 parameters	Δρ_max = 0.36 e Å⁻³
0 restraints	Δρ_min = −0.55 e Å⁻³

Crystal data top

C₂₃H₂₄Cl₂O₃	V = 2067.4 (4) Å³
M_r = 419.32	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 9.8154 (10) Å	µ = 0.34 mm⁻¹
b = 19.833 (2) Å	T = 296 K
c = 11.4441 (11) Å	0.20 × 0.10 × 0.10 mm
β = 111.873 (2)°

Data collection top

Bruker APEX CCD diffractometer	4961 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 1997)	3331 reflections with I > 2σ(I)
T_min = 0.936, T_max = 0.967	R_int = 0.027
13137 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.045	0 restraints
wR(F²) = 0.124	H-atom parameters constrained
S = 1.02	Δρ_max = 0.36 e Å⁻³
4961 reflections	Δρ_min = −0.55 e Å⁻³
257 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	0.48123 (7)	0.49352 (3)	0.81227 (5)	0.05835 (18)
Cl2	0.17633 (9)	0.68975 (4)	0.92235 (7)	0.0867 (3)
O1	0.37359 (14)	0.63325 (7)	0.31501 (11)	0.0429 (3)
O2	0.69826 (15)	0.60451 (8)	0.73455 (13)	0.0535 (4)
O3	0.19747 (16)	0.47392 (7)	0.52949 (13)	0.0495 (4)
C1	0.6678 (2)	0.63036 (10)	0.63116 (18)	0.0396 (4)
C2	0.7753 (2)	0.67506 (10)	0.60270 (19)	0.0437 (5)
H2A	0.8411	0.6468	0.5785	0.052*
H2B	0.8341	0.6986	0.6793	0.052*
C3	0.7073 (2)	0.72708 (10)	0.49949 (18)	0.0399 (4)
C4	0.6005 (2)	0.68988 (11)	0.38461 (18)	0.0447 (5)
H4A	0.5426	0.7227	0.3233	0.054*
H4B	0.6561	0.6637	0.3461	0.054*
C5	0.1471 (2)	0.57908 (11)	0.20690 (17)	0.0450 (5)
H5A	0.1701	0.5446	0.1569	0.054*
H5B	0.1296	0.6209	0.1598	0.054*
C6	0.0085 (2)	0.55903 (10)	0.22869 (18)	0.0409 (4)
C7	0.0469 (2)	0.49772 (10)	0.31638 (19)	0.0426 (4)
H7A	−0.0365	0.4871	0.3390	0.051*
H7B	0.0636	0.4594	0.2708	0.051*
C8	0.1799 (2)	0.50728 (9)	0.43512 (18)	0.0369 (4)
C9	0.42019 (19)	0.56963 (9)	0.55622 (16)	0.0336 (4)
H9	0.4699	0.5268	0.5881	0.040*
C10	0.52669 (18)	0.61624 (9)	0.52976 (16)	0.0345 (4)
C11	0.50031 (19)	0.64432 (9)	0.41722 (17)	0.0368 (4)
C12	0.27441 (19)	0.58782 (9)	0.32733 (17)	0.0363 (4)
C13	0.29182 (19)	0.55638 (9)	0.43501 (17)	0.0342 (4)
C14	−0.0441 (2)	0.61645 (11)	0.2899 (2)	0.0544 (6)
H14A	0.0286	0.6256	0.3717	0.082*
H14B	−0.1346	0.6038	0.2980	0.082*
H14C	−0.0595	0.6561	0.2385	0.082*
C15	−0.1116 (2)	0.54084 (13)	0.1031 (2)	0.0561 (6)
H15A	−0.1238	0.5771	0.0444	0.084*
H15B	−0.2022	0.5335	0.1151	0.084*
H15C	−0.0845	0.5005	0.0707	0.084*
C16	0.6252 (2)	0.78085 (11)	0.5432 (2)	0.0560 (6)
H16A	0.5859	0.8140	0.4782	0.084*
H16B	0.6917	0.8021	0.6181	0.084*
H16C	0.5465	0.7601	0.5608	0.084*
C17	0.8269 (2)	0.76069 (11)	0.4648 (2)	0.0512 (5)
H17A	0.8768	0.7272	0.4351	0.077*
H17B	0.8958	0.7826	0.5377	0.077*
H17C	0.7833	0.7935	0.3998	0.077*
C18	0.36693 (19)	0.59939 (9)	0.65453 (16)	0.0342 (4)
C19	0.3866 (2)	0.56903 (10)	0.76900 (17)	0.0384 (4)
C20	0.3308 (2)	0.59704 (11)	0.85255 (18)	0.0453 (5)
H20	0.3460	0.5763	0.9293	0.054*
C21	0.2526 (2)	0.65597 (11)	0.8201 (2)	0.0492 (5)
C22	0.2324 (2)	0.68823 (11)	0.7101 (2)	0.0521 (5)
H22	0.1810	0.7287	0.6903	0.063*
C23	0.2899 (2)	0.65966 (10)	0.62823 (19)	0.0441 (5)
H23	0.2765	0.6816	0.5529	0.053*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0722 (4)	0.0568 (3)	0.0467 (3)	0.0159 (3)	0.0229 (3)	0.0185 (2)
Cl2	0.1098 (6)	0.0919 (5)	0.0885 (5)	−0.0067 (4)	0.0717 (5)	−0.0323 (4)
O1	0.0408 (7)	0.0571 (8)	0.0295 (7)	−0.0146 (6)	0.0117 (6)	0.0025 (6)
O2	0.0466 (8)	0.0693 (10)	0.0385 (8)	−0.0043 (7)	0.0090 (6)	0.0099 (7)
O3	0.0550 (8)	0.0487 (8)	0.0469 (9)	−0.0060 (7)	0.0217 (7)	0.0081 (7)
C1	0.0378 (10)	0.0441 (11)	0.0370 (10)	0.0025 (8)	0.0139 (8)	−0.0023 (8)
C2	0.0358 (10)	0.0477 (11)	0.0460 (12)	−0.0039 (8)	0.0136 (9)	−0.0014 (9)
C3	0.0368 (9)	0.0430 (10)	0.0417 (11)	−0.0042 (8)	0.0165 (8)	−0.0025 (8)
C4	0.0445 (11)	0.0556 (12)	0.0362 (10)	−0.0118 (9)	0.0178 (9)	0.0004 (9)
C5	0.0427 (11)	0.0608 (13)	0.0305 (10)	−0.0103 (9)	0.0125 (8)	−0.0009 (9)
C6	0.0366 (9)	0.0465 (11)	0.0399 (10)	−0.0028 (8)	0.0145 (8)	0.0024 (8)
C7	0.0381 (10)	0.0425 (11)	0.0492 (12)	−0.0048 (8)	0.0187 (9)	0.0006 (9)
C8	0.0402 (10)	0.0335 (9)	0.0424 (11)	0.0010 (8)	0.0215 (8)	−0.0003 (8)
C9	0.0362 (9)	0.0351 (9)	0.0323 (9)	0.0024 (7)	0.0160 (8)	0.0009 (7)
C10	0.0331 (9)	0.0401 (10)	0.0320 (9)	0.0000 (7)	0.0143 (8)	−0.0012 (7)
C11	0.0340 (9)	0.0450 (10)	0.0324 (9)	−0.0049 (8)	0.0136 (8)	−0.0034 (8)
C12	0.0358 (9)	0.0415 (10)	0.0352 (10)	−0.0054 (8)	0.0174 (8)	−0.0026 (8)
C13	0.0352 (9)	0.0366 (9)	0.0341 (9)	0.0000 (7)	0.0167 (8)	−0.0017 (7)
C14	0.0524 (12)	0.0540 (13)	0.0575 (14)	0.0137 (10)	0.0210 (11)	0.0055 (10)
C15	0.0432 (11)	0.0692 (15)	0.0485 (13)	−0.0118 (11)	0.0084 (10)	0.0017 (11)
C16	0.0478 (12)	0.0498 (12)	0.0728 (16)	−0.0003 (10)	0.0252 (11)	−0.0086 (11)
C17	0.0466 (11)	0.0529 (12)	0.0578 (14)	−0.0114 (10)	0.0236 (10)	−0.0036 (10)
C18	0.0356 (9)	0.0382 (10)	0.0303 (9)	−0.0028 (7)	0.0139 (7)	−0.0010 (7)
C19	0.0401 (10)	0.0422 (10)	0.0318 (9)	−0.0035 (8)	0.0120 (8)	0.0005 (8)
C20	0.0506 (11)	0.0550 (12)	0.0338 (10)	−0.0132 (10)	0.0198 (9)	−0.0049 (9)
C21	0.0542 (12)	0.0544 (13)	0.0502 (13)	−0.0108 (10)	0.0322 (11)	−0.0170 (10)
C22	0.0553 (12)	0.0459 (12)	0.0600 (14)	0.0058 (10)	0.0270 (11)	−0.0067 (10)
C23	0.0521 (11)	0.0431 (11)	0.0396 (11)	0.0056 (9)	0.0202 (9)	0.0033 (8)

Geometric parameters (Å, º) top

Cl1—C19	1.734 (2)	C9—C10	1.508 (2)
Cl2—C21	1.741 (2)	C9—C13	1.509 (2)
O1—C11	1.371 (2)	C9—C18	1.525 (2)
O1—C12	1.372 (2)	C9—H9	0.9800
O2—C1	1.220 (2)	C10—C11	1.337 (2)
O3—C8	1.223 (2)	C12—C13	1.334 (2)
C1—C10	1.465 (3)	C14—H14A	0.9600
C1—C2	1.504 (3)	C14—H14B	0.9600
C2—C3	1.522 (3)	C14—H14C	0.9600
C2—H2A	0.9700	C15—H15A	0.9600
C2—H2B	0.9700	C15—H15B	0.9600
C3—C17	1.526 (3)	C15—H15C	0.9600
C3—C16	1.528 (3)	C16—H16A	0.9600
C3—C4	1.531 (3)	C16—H16B	0.9600
C4—C11	1.482 (3)	C16—H16C	0.9600
C4—H4A	0.9700	C17—H17A	0.9600
C4—H4B	0.9700	C17—H17B	0.9600
C5—C12	1.486 (3)	C17—H17C	0.9600
C5—C6	1.525 (3)	C18—C23	1.386 (3)
C5—H5A	0.9700	C18—C19	1.388 (2)
C5—H5B	0.9700	C19—C20	1.384 (3)
C6—C15	1.524 (3)	C20—C21	1.371 (3)
C6—C14	1.524 (3)	C20—H20	0.9300
C6—C7	1.531 (3)	C21—C22	1.360 (3)
C7—C8	1.505 (3)	C22—C23	1.383 (3)
C7—H7A	0.9700	C22—H22	0.9300
C7—H7B	0.9700	C23—H23	0.9300
C8—C13	1.468 (2)

C11—O1—C12	118.07 (14)	C10—C11—O1	122.95 (16)
O2—C1—C10	120.39 (18)	C10—C11—C4	126.02 (16)
O2—C1—C2	121.29 (17)	O1—C11—C4	111.03 (15)
C10—C1—C2	118.28 (17)	C13—C12—O1	123.39 (16)
C1—C2—C3	115.27 (15)	C13—C12—C5	125.20 (17)
C1—C2—H2A	108.5	O1—C12—C5	111.40 (15)
C3—C2—H2A	108.5	C12—C13—C8	118.18 (16)
C1—C2—H2B	108.5	C12—C13—C9	122.91 (16)
C3—C2—H2B	108.5	C8—C13—C9	118.91 (15)
H2A—C2—H2B	107.5	C6—C14—H14A	109.5
C2—C3—C17	109.89 (16)	C6—C14—H14B	109.5
C2—C3—C16	110.57 (17)	H14A—C14—H14B	109.5
C17—C3—C16	109.31 (17)	C6—C14—H14C	109.5
C2—C3—C4	107.56 (16)	H14A—C14—H14C	109.5
C17—C3—C4	109.51 (16)	H14B—C14—H14C	109.5
C16—C3—C4	109.97 (16)	C6—C15—H15A	109.5
C11—C4—C3	112.57 (16)	C6—C15—H15B	109.5
C11—C4—H4A	109.1	H15A—C15—H15B	109.5
C3—C4—H4A	109.1	C6—C15—H15C	109.5
C11—C4—H4B	109.1	H15A—C15—H15C	109.5
C3—C4—H4B	109.1	H15B—C15—H15C	109.5
H4A—C4—H4B	107.8	C3—C16—H16A	109.5
C12—C5—C6	111.83 (15)	C3—C16—H16B	109.5
C12—C5—H5A	109.2	H16A—C16—H16B	109.5
C6—C5—H5A	109.2	C3—C16—H16C	109.5
C12—C5—H5B	109.2	H16A—C16—H16C	109.5
C6—C5—H5B	109.2	H16B—C16—H16C	109.5
H5A—C5—H5B	107.9	C3—C17—H17A	109.5
C15—C6—C14	109.56 (17)	C3—C17—H17B	109.5
C15—C6—C5	109.34 (16)	H17A—C17—H17B	109.5
C14—C6—C5	110.85 (17)	C3—C17—H17C	109.5
C15—C6—C7	110.20 (17)	H17A—C17—H17C	109.5
C14—C6—C7	109.58 (17)	H17B—C17—H17C	109.5
C5—C6—C7	107.28 (16)	C23—C18—C19	116.87 (17)
C8—C7—C6	114.26 (16)	C23—C18—C9	118.85 (16)
C8—C7—H7A	108.7	C19—C18—C9	124.25 (16)
C6—C7—H7A	108.7	C20—C19—C18	121.75 (18)
C8—C7—H7B	108.7	C20—C19—Cl1	117.22 (15)
C6—C7—H7B	108.7	C18—C19—Cl1	121.03 (15)
H7A—C7—H7B	107.6	C21—C20—C19	118.76 (19)
O3—C8—C13	120.01 (17)	C21—C20—H20	120.6
O3—C8—C7	121.26 (17)	C19—C20—H20	120.6
C13—C8—C7	118.70 (16)	C22—C21—C20	121.69 (19)
C10—C9—C13	109.02 (14)	C22—C21—Cl2	119.39 (18)
C10—C9—C18	111.39 (14)	C20—C21—Cl2	118.91 (17)
C13—C9—C18	110.31 (14)	C21—C22—C23	118.6 (2)
C10—C9—H9	108.7	C21—C22—H22	120.7
C13—C9—H9	108.7	C23—C22—H22	120.7
C18—C9—H9	108.7	C22—C23—C18	122.25 (19)
C11—C10—C1	118.05 (17)	C22—C23—H23	118.9
C11—C10—C9	123.28 (16)	C18—C23—H23	118.9
C1—C10—C9	118.66 (16)

Experimental details

Crystal data
Chemical formula	C₂₃H₂₄Cl₂O₃
M_r	419.32
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	9.8154 (10), 19.833 (2), 11.4441 (11)
β (°)	111.873 (2)
V (Å³)	2067.4 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.34
Crystal size (mm)	0.20 × 0.10 × 0.10

Data collection
Diffractometer	Bruker APEX CCD
Absorption correction	Multi-scan (SADABS; Bruker, 1997)
T_min, T_max	0.936, 0.967
No. of measured, independent and observed [I > 2σ(I)] reflections	13137, 4961, 3331
R_int	0.027
(sin θ/λ)_max (Å⁻¹)	0.665

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.045, 0.124, 1.02
No. of reflections	4961
No. of parameters	257
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.36, −0.55

Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), SHELXTL (Sheldrick, 2008).

Acknowledgements

The research was supported by the Natural Science Foundation of Zhejiang Province (grant No. Y2090552). The author thanks Dr Dan Zhao of the Henan Polytechnic University for the data collection and structure refinement.

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