3-Ethoxy­carbonyl-1-phenyl-1H-pyrazol-5-yl 4-chloro­benzoate

Zheng, P.-W.; Fan, M.-L.; Duan, X.-M.; Li, J.-S.; Huang, P.-M.

doi:10.1107/S1600536805041954

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3-Ethoxycarbonyl-1-phenyl-1H-pyrazol-5-yl 4-chlorobenzoate

P.-W. Zheng, M.-L. Fan, X.-M. Duan, J.-S. Li and P.-M. Huang

In the title compound, C₁₉H₁₅ClN₂O₄, the molecules are held together by π–π stacking interactions. The ethyl group was found to be disordered.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805041954/wn6407sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536805041954/wn6407Isup2.hkl Contains datablock I

CCDC reference: 296729

checkCIF report

Key indicators

Single-crystal X-ray study
T = 294 K
Mean (C-C) = 0.004 Å
Disorder in main residue
R factor = 0.046
wR factor = 0.131
Data-to-parameter ratio = 15.2

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low ....         43 Perc.
PLAT031_ALERT_4_C Refined Extinction Parameter within Range ......       3.12 Sigma
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.79 Ratio
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C17
PLAT301_ALERT_3_C Main Residue  Disorder .........................       7.00 Perc.
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........          5
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      12.70 Deg.
              C8'  -O1   -C8      1.555   1.555   1.555

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   8 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   3 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion

Comment top

3-Substituted pyrazole derivatives have active biological properties (Vasilev et al., 1981; Kim et al., 1989; Hwang & Kim, 1994; Liu & Li, 2004). Recently, various new pyrazole derivatives have been prepared and their crystal structures reported by our group (Li, Li et al., 2005; Li, Duan et al., 2005; Guo et al., 2005; Duan et al., 2005). As a continuation of our project, the title compound, (I), was obtained via 4-chlorobenzoylation of commercially available ethyl 5-oxo-1-phenyl-2,5-dihydro-1H-pyrazole-3-carboxylate.

The molecular structure of (I) is illustrated in Fig. 1. The dihedral angle between the pyrazole and phenyl rings is 31.19 (15)°, that between the pyrazole and chlorophenyl rings is 74.32 (15)°.

In the crystal structure (Fig. 2), π–π stacking interactions are observed. There is a weak π–π interaction between the phenyl ring at (x, y, z) and that at (−x, 1/2 + y, 1/2 − z), with a centroid–centroid separation of 5.543 (2) Å. There is a strong π–π interaction between the chlorophenyl ring at (x, y, z) and that at (1 − x, 1 − y, 1 − z), with centroid–centroid and interplanar separations of 3.918 (18) and 3.491 Å, respectively.

Experimental top

The title compound was obtained, according to the method of Li, Li et al. (2005) as colorless needles (yield 84.0%, m.p. 394.5–395.7 K). Single crystals suitable for X-ray diffraction were grown from a solution of ethyl acetate/n-hexane (1:1 v/v).

Computing details top

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

Figures top

	Fig. 1. The molecular structure of (I), with the atom-numbering scheme and displacement ellipsoids drawn at the 30% probability level. Only the major component of the disordered ethyl group is shown.
	Fig. 2. A partial packing diagram for (I). The molecules are held together by π–π stacking interactions. Only the major component of the disordered ethyl group is shown.

3-ethoxycarbonyl-1-phenyl-1H-pyrazol-5-yl 4-chlorobenzoate top

Crystal data top

C₁₉H₁₅ClN₂O₄	F(000) = 768
M_r = 370.78	D_x = 1.363 Mg m⁻³
Monoclinic, P2₁/c	Melting point = 394.5–395.7 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 13.426 (3) Å	Cell parameters from 1480 reflections
b = 5.9078 (11) Å	θ = 2.6–20.3°
c = 23.142 (4) Å	µ = 0.24 mm⁻¹
β = 100.051 (3)°	T = 294 K
V = 1807.4 (6) Å³	Needle, colorless
Z = 4	0.20 × 0.12 × 0.10 mm

Data collection top

Bruker SMART 1000 CCD area-detector diffractometer	3700 independent reflections
Radiation source: fine-focus sealed tube	1603 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.053
ϕ and ω scans	θ_max = 26.4°, θ_min = 1.5°
Absorption correction: multi-scan (SADABS; Bruker, 1997)	h = −16→16
T_min = 0.954, T_max = 0.977	k = −7→3
9758 measured reflections	l = −28→27

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)] = 0.046	H-atom parameters constrained
wR(F²) = 0.131	w = 1/[σ²(F_o²) + (0.0536P)²] where P = (F_o² + 2F_c²)/3
S = 0.97	(Δ/σ)_max < 0.001
3700 reflections	Δρ_max = 0.21 e Å⁻³
243 parameters	Δρ_min = −0.17 e Å⁻³
4 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc2^λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0025 (8)

Crystal data top

C₁₉H₁₅ClN₂O₄	V = 1807.4 (6) Å³
M_r = 370.78	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 13.426 (3) Å	µ = 0.24 mm⁻¹
b = 5.9078 (11) Å	T = 294 K
c = 23.142 (4) Å	0.20 × 0.12 × 0.10 mm
β = 100.051 (3)°

Data collection top

Bruker SMART 1000 CCD area-detector diffractometer	3700 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 1997)	1603 reflections with I > 2σ(I)
T_min = 0.954, T_max = 0.977	R_int = 0.053
9758 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.046	4 restraints
wR(F²) = 0.131	H-atom parameters constrained
S = 0.97	Δρ_max = 0.21 e Å⁻³
3700 reflections	Δρ_min = −0.17 e Å⁻³
243 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	Occ. (<1)
Cl1	0.21556 (7)	0.23298 (18)	0.46502 (4)	0.1156 (4)
O1	0.80920 (15)	1.1753 (4)	0.85760 (10)	0.1006 (8)
O2	0.65999 (16)	1.3456 (4)	0.82697 (9)	0.0864 (7)
O3	0.57029 (12)	0.6651 (3)	0.66820 (8)	0.0616 (5)
O4	0.56931 (15)	0.9459 (4)	0.60236 (9)	0.0837 (7)
N1	0.73063 (15)	0.7357 (4)	0.72675 (9)	0.0545 (6)
N2	0.77464 (16)	0.8733 (4)	0.77069 (9)	0.0599 (6)
C1	0.79160 (19)	0.5753 (5)	0.70214 (10)	0.0519 (7)
C2	0.8921 (2)	0.6267 (5)	0.70327 (12)	0.0655 (8)
H2	0.9191	0.7626	0.7192	0.079*
C3	0.9521 (2)	0.4720 (6)	0.68017 (14)	0.0779 (9)
H3	1.0202	0.5035	0.6807	0.094*
C4	0.9115 (3)	0.2724 (6)	0.65650 (14)	0.0845 (10)
H4	0.9521	0.1693	0.6410	0.101*
C5	0.8117 (3)	0.2246 (5)	0.65561 (13)	0.0789 (9)
H5	0.7846	0.0895	0.6392	0.095*
C6	0.7508 (2)	0.3750 (5)	0.67887 (12)	0.0639 (8)
H6	0.6831	0.3413	0.6788	0.077*
C7'	0.9360 (17)	1.336 (4)	0.9308 (12)	0.144 (6)	0.462 (18)
H7'A	0.9548	1.4722	0.9524	0.216*	0.462 (18)
H7'B	0.9745	1.3224	0.8997	0.216*	0.462 (18)
H7'C	0.9495	1.2077	0.9565	0.216*	0.462 (18)
C8'	0.8246 (19)	1.343 (4)	0.9051 (10)	0.133 (3)	0.462 (18)
H8'A	0.7844	1.3049	0.9347	0.159*	0.462 (18)
H8'B	0.8054	1.4926	0.8899	0.159*	0.462 (18)
C7	0.9132 (15)	1.235 (4)	0.9469 (10)	0.144 (6)	0.538 (18)
H7A	0.9278	1.3293	0.9811	0.216*	0.538 (18)
H7B	0.9750	1.1981	0.9336	0.216*	0.538 (18)
H7C	0.8810	1.0983	0.9565	0.216*	0.538 (18)
C8	0.8437 (18)	1.359 (3)	0.8991 (8)	0.133 (3)	0.538 (18)
H8A	0.7875	1.4284	0.9139	0.159*	0.538 (18)
H8B	0.8797	1.4750	0.8812	0.159*	0.538 (18)
C9	0.7193 (2)	1.1958 (6)	0.82344 (14)	0.0720 (9)
C10	0.7000 (2)	1.0107 (5)	0.78033 (12)	0.0600 (7)
C11	0.6086 (2)	0.9636 (5)	0.74324 (12)	0.0639 (8)
H11A	0.5465	1.0355	0.7417	0.077*
C12	0.63142 (19)	0.7894 (5)	0.71022 (12)	0.0562 (7)
C13	0.53768 (19)	0.7668 (5)	0.61449 (12)	0.0561 (7)
C14	0.46078 (18)	0.6257 (5)	0.57774 (11)	0.0517 (7)
C15	0.43060 (19)	0.4192 (5)	0.59615 (12)	0.0602 (7)
H15A	0.4612	0.3620	0.6324	0.072*
C16	0.3562 (2)	0.2967 (5)	0.56193 (14)	0.0734 (9)
H16A	0.3360	0.1575	0.5747	0.088*
C17	0.3118 (2)	0.3820 (6)	0.50862 (14)	0.0710 (8)
C18	0.3416 (2)	0.5875 (6)	0.48863 (13)	0.0730 (9)
H18A	0.3113	0.6430	0.4522	0.088*
C19	0.4167 (2)	0.7088 (5)	0.52337 (12)	0.0648 (8)
H19A	0.4379	0.8466	0.5103	0.078*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0910 (7)	0.1318 (9)	0.1103 (8)	−0.0283 (6)	−0.0206 (5)	−0.0321 (6)
O1	0.0611 (14)	0.131 (2)	0.1058 (17)	−0.0026 (13)	0.0030 (13)	−0.0619 (15)
O2	0.0715 (15)	0.0851 (16)	0.1049 (17)	−0.0034 (12)	0.0220 (13)	−0.0196 (14)
O3	0.0485 (11)	0.0661 (12)	0.0649 (13)	−0.0092 (9)	−0.0052 (9)	0.0053 (10)
O4	0.0903 (16)	0.0763 (15)	0.0792 (15)	−0.0295 (12)	0.0001 (12)	0.0126 (12)
N1	0.0418 (13)	0.0642 (15)	0.0551 (14)	−0.0035 (11)	0.0019 (11)	−0.0046 (12)
N2	0.0489 (13)	0.0726 (16)	0.0564 (14)	−0.0084 (13)	0.0045 (11)	−0.0073 (12)
C1	0.0459 (16)	0.0605 (19)	0.0468 (16)	0.0015 (14)	0.0009 (13)	0.0043 (13)
C2	0.0489 (18)	0.076 (2)	0.0681 (19)	0.0017 (16)	0.0013 (15)	0.0014 (16)
C3	0.0531 (19)	0.097 (3)	0.083 (2)	0.011 (2)	0.0108 (17)	0.012 (2)
C4	0.088 (3)	0.084 (3)	0.083 (2)	0.028 (2)	0.018 (2)	0.003 (2)
C5	0.091 (3)	0.065 (2)	0.077 (2)	0.008 (2)	0.0030 (19)	0.0007 (17)
C6	0.0605 (18)	0.064 (2)	0.0653 (19)	−0.0012 (17)	0.0042 (15)	0.0051 (16)
C7'	0.092 (9)	0.193 (17)	0.142 (12)	−0.049 (7)	0.009 (6)	−0.078 (12)
C8'	0.061 (8)	0.174 (5)	0.156 (5)	0.009 (4)	0.000 (4)	−0.104 (4)
C7	0.092 (9)	0.193 (17)	0.142 (12)	−0.049 (7)	0.009 (6)	−0.078 (12)
C8	0.061 (8)	0.174 (5)	0.156 (5)	0.009 (4)	0.000 (4)	−0.104 (4)
C9	0.054 (2)	0.086 (3)	0.079 (2)	−0.0139 (18)	0.0201 (18)	−0.014 (2)
C10	0.0480 (17)	0.072 (2)	0.0618 (18)	−0.0081 (16)	0.0136 (15)	−0.0041 (16)
C11	0.0438 (16)	0.077 (2)	0.071 (2)	−0.0016 (15)	0.0102 (15)	−0.0012 (17)
C12	0.0404 (16)	0.0666 (19)	0.0581 (18)	−0.0077 (14)	−0.0014 (13)	0.0026 (15)
C13	0.0458 (16)	0.065 (2)	0.0571 (18)	0.0022 (15)	0.0084 (14)	0.0043 (16)
C14	0.0422 (15)	0.0604 (18)	0.0528 (17)	−0.0012 (14)	0.0093 (13)	−0.0025 (14)
C15	0.0592 (18)	0.0616 (19)	0.0575 (17)	−0.0029 (15)	0.0038 (14)	0.0026 (15)
C16	0.071 (2)	0.071 (2)	0.075 (2)	−0.0122 (17)	0.0044 (18)	−0.0052 (17)
C17	0.0556 (18)	0.085 (2)	0.070 (2)	−0.0073 (17)	0.0033 (16)	−0.0161 (19)
C18	0.067 (2)	0.090 (2)	0.0557 (18)	0.0051 (18)	−0.0072 (16)	−0.0045 (18)
C19	0.0612 (18)	0.073 (2)	0.0584 (19)	−0.0038 (16)	0.0061 (15)	0.0047 (16)

Geometric parameters (Å, º) top

Cl1—C17	1.734 (3)	C7'—H7'B	0.9600
O1—C9	1.327 (3)	C7'—H7'C	0.9600
O1—C8'	1.466 (9)	C8'—H8'A	0.9700
O1—C8	1.471 (8)	C8'—H8'B	0.9700
O2—C9	1.203 (3)	C7—C8	1.509 (10)
O3—C12	1.371 (3)	C7—H7A	0.9600
O3—C13	1.381 (3)	C7—H7B	0.9600
O4—C13	1.192 (3)	C7—H7C	0.9600
N1—N2	1.354 (3)	C8—H8A	0.9700
N1—C12	1.358 (3)	C8—H8B	0.9700
N1—C1	1.434 (3)	C9—C10	1.473 (4)
N2—C10	1.338 (3)	C10—C11	1.398 (3)
C1—C6	1.374 (4)	C11—C12	1.349 (3)
C1—C2	1.379 (3)	C11—H11A	0.9300
C2—C3	1.386 (4)	C13—C14	1.476 (4)
C2—H2	0.9300	C14—C15	1.377 (3)
C3—C4	1.372 (4)	C14—C19	1.384 (3)
C3—H3	0.9300	C15—C16	1.368 (3)
C4—C5	1.366 (4)	C15—H15A	0.9300
C4—H4	0.9300	C16—C17	1.369 (4)
C5—C6	1.379 (4)	C16—H16A	0.9300
C5—H5	0.9300	C17—C18	1.383 (4)
C6—H6	0.9300	C18—C19	1.376 (4)
C7'—C8'	1.510 (10)	C18—H18A	0.9300
C7'—H7'A	0.9600	C19—H19A	0.9300

C9—O1—C8'	112.3 (11)	H7A—C7—H7C	109.5
C9—O1—C8	118.1 (10)	H7B—C7—H7C	109.5
C8'—O1—C8	12.7 (18)	O1—C8—C7	101.7 (13)
C12—O3—C13	117.5 (2)	O1—C8—H8A	111.4
N2—N1—C12	110.4 (2)	C7—C8—H8A	111.4
N2—N1—C1	119.4 (2)	O1—C8—H8B	111.4
C12—N1—C1	130.0 (2)	C7—C8—H8B	111.4
C10—N2—N1	104.4 (2)	H8A—C8—H8B	109.3
C6—C1—C2	121.3 (3)	O2—C9—O1	124.8 (3)
C6—C1—N1	120.6 (2)	O2—C9—C10	123.5 (3)
C2—C1—N1	118.1 (2)	O1—C9—C10	111.7 (3)
C1—C2—C3	118.7 (3)	N2—C10—C11	112.3 (2)
C1—C2—H2	120.6	N2—C10—C9	121.0 (3)
C3—C2—H2	120.6	C11—C10—C9	126.6 (3)
C4—C3—C2	120.2 (3)	C12—C11—C10	103.7 (2)
C4—C3—H3	119.9	C12—C11—H11A	128.1
C2—C3—H3	119.9	C10—C11—H11A	128.1
C5—C4—C3	120.3 (3)	C11—C12—N1	109.1 (2)
C5—C4—H4	119.8	C11—C12—O3	130.0 (2)
C3—C4—H4	119.8	N1—C12—O3	120.7 (3)
C4—C5—C6	120.5 (3)	O4—C13—O3	121.9 (3)
C4—C5—H5	119.8	O4—C13—C14	127.4 (3)
C6—C5—H5	119.8	O3—C13—C14	110.7 (2)
C1—C6—C5	119.1 (3)	C15—C14—C19	119.6 (3)
C1—C6—H6	120.5	C15—C14—C13	122.4 (3)
C5—C6—H6	120.5	C19—C14—C13	118.0 (3)
C8'—C7'—H7'A	109.5	C16—C15—C14	120.9 (3)
C8'—C7'—H7'B	109.5	C16—C15—H15A	119.5
H7'A—C7'—H7'B	109.5	C14—C15—H15A	119.5
C8'—C7'—H7'C	109.5	C15—C16—C17	119.1 (3)
H7'A—C7'—H7'C	109.5	C15—C16—H16A	120.5
H7'B—C7'—H7'C	109.5	C17—C16—H16A	120.5
O1—C8'—C7'	106.1 (16)	C16—C17—C18	121.2 (3)
O1—C8'—H8'A	110.5	C16—C17—Cl1	120.0 (3)
C7'—C8'—H8'A	110.5	C18—C17—Cl1	118.8 (3)
O1—C8'—H8'B	110.5	C19—C18—C17	119.2 (3)
C7'—C8'—H8'B	110.5	C19—C18—H18A	120.4
H8'A—C8'—H8'B	108.7	C17—C18—H18A	120.4
C8—C7—H7A	109.5	C18—C19—C14	120.0 (3)
C8—C7—H7B	109.5	C18—C19—H19A	120.0
H7A—C7—H7B	109.5	C14—C19—H19A	120.0
C8—C7—H7C	109.5

C12—N1—N2—C10	0.0 (3)	O1—C9—C10—C11	170.9 (3)
C1—N1—N2—C10	175.5 (2)	N2—C10—C11—C12	−0.1 (3)
N2—N1—C1—C6	150.6 (2)	C9—C10—C11—C12	176.3 (3)
C12—N1—C1—C6	−34.9 (4)	C10—C11—C12—N1	0.1 (3)
N2—N1—C1—C2	−28.6 (3)	C10—C11—C12—O3	176.4 (3)
C12—N1—C1—C2	145.9 (3)	N2—N1—C12—C11	−0.1 (3)
C6—C1—C2—C3	0.2 (4)	C1—N1—C12—C11	−174.9 (2)
N1—C1—C2—C3	179.3 (2)	N2—N1—C12—O3	−176.8 (2)
C1—C2—C3—C4	0.3 (4)	C1—N1—C12—O3	8.3 (4)
C2—C3—C4—C5	−0.1 (5)	C13—O3—C12—C11	74.0 (3)
C3—C4—C5—C6	−0.5 (5)	C13—O3—C12—N1	−110.0 (3)
C2—C1—C6—C5	−0.8 (4)	C12—O3—C13—O4	7.8 (4)
N1—C1—C6—C5	−179.9 (2)	C12—O3—C13—C14	−171.3 (2)
C4—C5—C6—C1	1.0 (4)	O4—C13—C14—C15	179.3 (3)
C9—O1—C8'—C7'	−167.0 (15)	O3—C13—C14—C15	−1.7 (3)
C8—O1—C8'—C7'	−47 (9)	O4—C13—C14—C19	−2.0 (4)
C9—O1—C8—C7	152.7 (12)	O3—C13—C14—C19	177.0 (2)
C8'—O1—C8—C7	87 (10)	C19—C14—C15—C16	−1.3 (4)
C8'—O1—C9—O2	6.3 (13)	C13—C14—C15—C16	177.4 (2)
C8—O1—C9—O2	−6.2 (11)	C14—C15—C16—C17	0.2 (4)
C8'—O1—C9—C10	−173.3 (12)	C15—C16—C17—C18	0.8 (4)
C8—O1—C9—C10	174.1 (10)	C15—C16—C17—Cl1	−178.7 (2)
N1—N2—C10—C11	0.0 (3)	C16—C17—C18—C19	−0.6 (4)
N1—N2—C10—C9	−176.6 (2)	Cl1—C17—C18—C19	178.9 (2)
O2—C9—C10—N2	167.3 (3)	C17—C18—C19—C14	−0.5 (4)
O1—C9—C10—N2	−13.0 (4)	C15—C14—C19—C18	1.5 (4)
O2—C9—C10—C11	−8.8 (5)	C13—C14—C19—C18	−177.3 (2)

Experimental details

Crystal data
Chemical formula	C₁₉H₁₅ClN₂O₄
M_r	370.78
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	294
a, b, c (Å)	13.426 (3), 5.9078 (11), 23.142 (4)
β (°)	100.051 (3)
V (Å³)	1807.4 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.24
Crystal size (mm)	0.20 × 0.12 × 0.10

Data collection
Diffractometer	Bruker SMART 1000 CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 1997)
T_min, T_max	0.954, 0.977
No. of measured, independent and observed [I > 2σ(I)] reflections	9758, 3700, 1603
R_int	0.053
(sin θ/λ)_max (Å⁻¹)	0.626

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.046, 0.131, 0.97
No. of reflections	3700
No. of parameters	243
No. of restraints	4
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.21, −0.17

Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1997), SHELXTL.

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