1-(4-tert-Butyl­benz­yl)-3-(4-chloro­phenyl)-1H-pyrazole-5-carboxylic acid

Ding, X.-L.; Dong, W.-L.; Xia, Y.; Zhao, B.-X.

doi:10.1107/S1600536807027006

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1-(4-tert-Butylbenzyl)-3-(4-chlorophenyl)-1H-pyrazole-5-carboxylic acid

X.-L. Ding, W.-L. Dong, Y. Xia and B.-X. Zhao

In the title compound, C₂₁H₂₁ClN₂O₂, the pyrazole and chlorobenzene rings are coplanar and make a dihedral angle of 79.7 (2)° with the tert-butylbenzene ring. The crystal structure displays intermolecular O—H

O hydrogen bonding.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807027006/bg2063sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807027006/bg2063Isup2.hkl Contains datablock I

CCDC reference: 654891

checkCIF report

Key indicators

Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.004 Å
R factor = 0.050
wR factor = 0.182
Data-to-parameter ratio = 18.4

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT242_ALERT_2_B Check Low       Ueq as Compared to Neighbors for        C18

Alert level C
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C18    -   C19     ..       5.07 su
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C16
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C17
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         C1
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C12
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C15

Alert level G
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature .        293 K

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

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   7 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Comment top

The pyrazole framework plays an essential role in biologically active compounds. Many pyrazole derivatives are known to exhibit a wide range of biological properties such as anticoagulant (Jia et al., 2004), antipyretic, antibacterial, hypoglycaemic, antihyperglycaemic, analgesic, anti-inflammatory, sedative–hypnotic (Cottineau et al., 2002; Finn et al., 2003), and antitumour (Wei et al., 2006) activities.

In the title compound, C₂₁H₂₁ClN₂O₂ (I), shown in Fig. 1, the pyrazole (C7—C9/N1/N2) and benzene (C1—C6) rings are coplanar within 0.01° and subtend a dihedral angle of 79.7 (2)° with the tert-butylbenzyl ring (C12—C17). The crystal structure displays a strong intermolecular O2—H2A···O1 interaction which leads to formation of hydrogen bonded dimeric units (Table 1 and Fig. 2).

Related literature top

For related literature, see: Jia et al. (2004); Cottineau et al. (2002); Finn et al. (2003); Wei et al. (2006); Xia et al. (2007).

Experimental top

A mixture of ethyl 1-(4-tert-butylbenzyl)-3-(4-chlorophenyl)-1H-pyrazole-5-carboxylate (0.01 mol) that was synthesized according to a literature procedure (Xia et al., 2007) and potassium hydroxide (0.02 mol) in ethanol (40 ml) was heated to reflux for 3 h. The solvent was removed under reduced pressure and the residue was dissolved in water and acidified with hydrochloric acid (10%). The precipitate was filtered and dried to give a white solid (yield 95%). Crystals of (I) suitable for X-ray diffraction were obtained by slow evaporation of a solution of the solid in acetone at room temperature for 3 d.

Structure description top

For related literature, see: Jia et al. (2004); Cottineau et al. (2002); Finn et al. (2003); Wei et al. (2006); Xia et al. (2007).

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2; data reduction: APEX2; program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top

	Fig. 1. The molecular structure of (I), showing displacement ellipsoids drawn at the 50% probability level for non-H atoms.
	Fig. 2. Packing view of (I), shown down the a axis. Hydrogen bonds leading to dimeric units are drawn as dashed lines.

1-(4-tert-Butylbenzyl)-3-(4-chlorophenyl)-1H-pyrazole-5-carboxylic acid top

Crystal data top

C₂₁H₂₁ClN₂O₂	Z = 2
M_r = 368.85	F(000) = 388
Triclinic, P1	D_x = 1.269 Mg m⁻³
a = 6.6835 (1) Å	Mo Kα radiation, λ = 0.71073 Å
b = 12.3218 (3) Å	Cell parameters from 3163 reflections
c = 12.6783 (3) Å	θ = 2.8–23.6°
α = 105.714 (2)°	µ = 0.22 mm⁻¹
β = 102.714 (1)°	T = 293 K
γ = 96.003 (2)°	Plate, colourless
V = 965.32 (4) Å³	0.48 × 0.24 × 0.09 mm

Data collection top

Bruker APEX II CCD area-detector diffractometer	4403 independent reflections
Radiation source: fine-focus sealed tube	2700 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.026
φ and ω scans	θ_max = 27.5°, θ_min = 1.7°
Absorption correction: multi-scan (APEX2; Bruker, 2005)	h = −8→8
T_min = 0.905, T_max = 0.980	k = −15→15
15167 measured reflections	l = −16→16

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)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.182	H-atom parameters constrained
S = 0.92	w = 1/[σ²(F_o²) + (0.1P)² + 0.244P] where P = (F_o² + 2F_c²)/3
4403 reflections	(Δ/σ)_max < 0.001
239 parameters	Δρ_max = 0.26 e Å⁻³
0 restraints	Δρ_min = −0.17 e Å⁻³

Crystal data top

C₂₁H₂₁ClN₂O₂	γ = 96.003 (2)°
M_r = 368.85	V = 965.32 (4) Å³
Triclinic, P1	Z = 2
a = 6.6835 (1) Å	Mo Kα radiation
b = 12.3218 (3) Å	µ = 0.22 mm⁻¹
c = 12.6783 (3) Å	T = 293 K
α = 105.714 (2)°	0.48 × 0.24 × 0.09 mm
β = 102.714 (1)°

Data collection top

Bruker APEX II CCD area-detector diffractometer	4403 independent reflections
Absorption correction: multi-scan (APEX2; Bruker, 2005)	2700 reflections with I > 2σ(I)
T_min = 0.905, T_max = 0.980	R_int = 0.026
15167 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.050	0 restraints
wR(F²) = 0.182	H-atom parameters constrained
S = 0.92	Δρ_max = 0.26 e Å⁻³
4403 reflections	Δρ_min = −0.17 e Å⁻³
239 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	0.1226 (4)	0.07086 (19)	0.3376 (2)	0.0712 (6)
C2	0.2138 (4)	0.1251 (2)	0.2756 (2)	0.0882 (8)
H2	0.1396	0.1232	0.2037	0.106*
C3	0.4169 (4)	0.1832 (2)	0.3194 (2)	0.0844 (7)
H3	0.4781	0.2203	0.2764	0.101*
C4	0.5299 (3)	0.18702 (17)	0.42565 (18)	0.0614 (5)
C5	0.4330 (4)	0.1310 (2)	0.4865 (2)	0.0762 (6)
H5	0.5053	0.1331	0.5588	0.091*
C6	0.2311 (4)	0.0718 (2)	0.4422 (2)	0.0829 (7)
H6	0.1697	0.0329	0.4836	0.099*
C7	0.7457 (3)	0.24819 (16)	0.47313 (18)	0.0604 (5)
C8	0.8730 (3)	0.30918 (17)	0.42691 (18)	0.0627 (5)
H8	0.8383	0.3212	0.3563	0.075*
C9	1.0592 (3)	0.34740 (16)	0.50741 (18)	0.0603 (5)
C10	1.2526 (4)	0.41398 (17)	0.50558 (19)	0.0635 (5)
C11	1.1879 (4)	0.32868 (19)	0.7064 (2)	0.0723 (6)
H11A	1.3256	0.3220	0.6951	0.087*
H11B	1.1483	0.2699	0.7392	0.087*
C12	1.1974 (3)	0.44418 (19)	0.78821 (18)	0.0649 (5)
C13	1.0193 (4)	0.4834 (2)	0.8071 (2)	0.0868 (8)
H13	0.8903	0.4379	0.7676	0.104*
C14	1.0277 (4)	0.5887 (2)	0.8832 (2)	0.0891 (8)
H14	0.9038	0.6122	0.8937	0.107*
C15	1.2125 (3)	0.65996 (19)	0.94393 (18)	0.0669 (6)
C16	1.3897 (4)	0.6194 (3)	0.9236 (3)	0.1062 (11)
H16	1.5190	0.6646	0.9627	0.127*
C17	1.3814 (4)	0.5149 (3)	0.8477 (3)	0.1017 (10)
H17	1.5051	0.4916	0.8364	0.122*
C18	1.2253 (4)	0.7780 (2)	1.0281 (2)	0.0778 (6)
C19	1.0071 (5)	0.8031 (3)	1.0371 (3)	0.1174 (11)
H19A	0.9430	0.7489	1.0670	0.176*
H19B	0.9226	0.7969	0.9632	0.176*
H19C	1.0201	0.8792	1.0867	0.176*
C20	1.3529 (7)	0.7854 (3)	1.1457 (3)	0.1262 (13)
H20A	1.2867	0.7292	1.1725	0.189*
H20B	1.3622	0.8604	1.1966	0.189*
H20C	1.4902	0.7713	1.1422	0.189*
C21	1.3251 (7)	0.8704 (3)	0.9879 (4)	0.1315 (13)
H21A	1.3187	0.9444	1.0358	0.197*
H21B	1.2517	0.8617	0.9111	0.197*
H21C	1.4680	0.8635	0.9913	0.197*
Cl1	−0.13478 (10)	−0.00033 (6)	0.28340 (6)	0.0938 (3)
N1	0.8497 (3)	0.24867 (15)	0.57708 (16)	0.0668 (5)
N2	1.0407 (3)	0.30882 (14)	0.59649 (15)	0.0643 (5)
O1	1.4087 (3)	0.44336 (14)	0.58439 (14)	0.0768 (4)
O2	1.2374 (3)	0.43813 (15)	0.41032 (14)	0.0803 (5)
H2A	1.3497	0.4729	0.4113	0.120*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0608 (13)	0.0616 (12)	0.0773 (14)	0.0088 (10)	0.0171 (11)	−0.0002 (10)
C2	0.0760 (16)	0.1025 (19)	0.0709 (15)	−0.0056 (14)	0.0053 (13)	0.0204 (14)
C3	0.0798 (16)	0.0944 (17)	0.0725 (15)	−0.0052 (13)	0.0172 (13)	0.0241 (13)
C4	0.0611 (12)	0.0511 (10)	0.0671 (12)	0.0102 (9)	0.0197 (10)	0.0072 (9)
C5	0.0665 (14)	0.0834 (15)	0.0759 (14)	0.0050 (12)	0.0143 (12)	0.0262 (12)
C6	0.0690 (15)	0.0851 (16)	0.0945 (18)	0.0018 (12)	0.0243 (14)	0.0289 (14)
C7	0.0623 (12)	0.0483 (10)	0.0639 (12)	0.0077 (9)	0.0169 (10)	0.0062 (8)
C8	0.0688 (13)	0.0545 (11)	0.0613 (11)	0.0077 (9)	0.0187 (10)	0.0112 (9)
C9	0.0655 (12)	0.0469 (10)	0.0656 (12)	0.0084 (9)	0.0211 (10)	0.0096 (9)
C10	0.0679 (13)	0.0520 (10)	0.0676 (13)	0.0081 (9)	0.0220 (11)	0.0106 (9)
C11	0.0684 (14)	0.0708 (13)	0.0747 (14)	0.0067 (11)	0.0081 (11)	0.0274 (11)
C12	0.0578 (12)	0.0715 (13)	0.0630 (12)	0.0026 (10)	0.0092 (10)	0.0247 (10)
C13	0.0565 (13)	0.0803 (16)	0.1011 (19)	−0.0058 (11)	0.0084 (13)	0.0070 (14)
C14	0.0572 (14)	0.0888 (17)	0.1026 (19)	0.0058 (12)	0.0121 (13)	0.0083 (14)
C15	0.0597 (12)	0.0746 (13)	0.0606 (12)	−0.0040 (10)	0.0091 (10)	0.0219 (10)
C16	0.0536 (14)	0.114 (2)	0.108 (2)	−0.0141 (14)	0.0096 (14)	−0.0162 (18)
C17	0.0515 (13)	0.111 (2)	0.111 (2)	0.0024 (13)	0.0132 (14)	−0.0079 (17)
C18	0.0788 (16)	0.0740 (14)	0.0697 (14)	−0.0030 (12)	0.0123 (12)	0.0157 (11)
C19	0.109 (2)	0.111 (2)	0.113 (2)	0.0151 (19)	0.035 (2)	−0.0011 (19)
C20	0.160 (3)	0.107 (2)	0.0766 (18)	0.007 (2)	−0.008 (2)	0.0073 (17)
C21	0.158 (3)	0.089 (2)	0.157 (3)	0.001 (2)	0.065 (3)	0.043 (2)
Cl1	0.0648 (4)	0.0897 (5)	0.1040 (5)	−0.0023 (3)	0.0161 (3)	0.0024 (4)
N1	0.0624 (11)	0.0606 (10)	0.0721 (11)	0.0007 (8)	0.0161 (9)	0.0165 (8)
N2	0.0618 (11)	0.0580 (9)	0.0677 (11)	0.0046 (8)	0.0137 (9)	0.0153 (8)
O1	0.0684 (10)	0.0830 (11)	0.0738 (10)	−0.0029 (8)	0.0172 (8)	0.0226 (8)
O2	0.0777 (11)	0.0827 (11)	0.0757 (10)	−0.0071 (9)	0.0174 (8)	0.0262 (8)

Geometric parameters (Å, º) top

C1—C2	1.359 (4)	C12—C13	1.375 (3)
C1—C6	1.360 (4)	C13—C14	1.379 (4)
C1—Cl1	1.743 (2)	C13—H13	0.9300
C2—C3	1.383 (4)	C14—C15	1.370 (3)
C2—H2	0.9300	C14—H14	0.9300
C3—C4	1.378 (3)	C15—C16	1.381 (4)
C3—H3	0.9300	C15—C18	1.534 (3)
C4—C5	1.380 (3)	C16—C17	1.371 (4)
C4—C7	1.468 (3)	C16—H16	0.9300
C5—C6	1.381 (3)	C17—H17	0.9300
C5—H5	0.9300	C18—C21	1.519 (4)
C6—H6	0.9300	C18—C20	1.519 (4)
C7—N1	1.346 (3)	C18—C19	1.544 (4)
C7—C8	1.399 (3)	C19—H19A	0.9600
C8—C9	1.368 (3)	C19—H19B	0.9600
C8—H8	0.9300	C19—H19C	0.9600
C9—N2	1.363 (3)	C20—H20A	0.9600
C9—C10	1.465 (3)	C20—H20B	0.9600
C10—O1	1.218 (3)	C20—H20C	0.9600
C10—O2	1.306 (3)	C21—H21A	0.9600
C11—N2	1.460 (3)	C21—H21B	0.9600
C11—C12	1.503 (3)	C21—H21C	0.9600
C11—H11A	0.9700	N1—N2	1.343 (2)
C11—H11B	0.9700	O2—H2A	0.8200
C12—C17	1.361 (3)

C2—C1—C6	120.3 (2)	C15—C14—C13	122.2 (2)
C2—C1—Cl1	120.1 (2)	C15—C14—H14	118.9
C6—C1—Cl1	119.6 (2)	C13—C14—H14	118.9
C1—C2—C3	120.1 (3)	C14—C15—C16	115.6 (2)
C1—C2—H2	119.9	C14—C15—C18	123.1 (2)
C3—C2—H2	119.9	C16—C15—C18	121.4 (2)
C4—C3—C2	120.9 (2)	C17—C16—C15	122.3 (2)
C4—C3—H3	119.5	C17—C16—H16	118.9
C2—C3—H3	119.5	C15—C16—H16	118.9
C3—C4—C5	117.6 (2)	C12—C17—C16	121.8 (2)
C3—C4—C7	121.5 (2)	C12—C17—H17	119.1
C5—C4—C7	120.8 (2)	C16—C17—H17	119.1
C4—C5—C6	121.4 (2)	C21—C18—C20	109.4 (3)
C4—C5—H5	119.3	C21—C18—C15	109.6 (2)
C6—C5—H5	119.3	C20—C18—C15	110.7 (2)
C1—C6—C5	119.6 (2)	C21—C18—C19	107.3 (3)
C1—C6—H6	120.2	C20—C18—C19	108.1 (3)
C5—C6—H6	120.2	C15—C18—C19	111.6 (2)
N1—C7—C8	110.39 (19)	C18—C19—H19A	109.5
N1—C7—C4	119.21 (19)	C18—C19—H19B	109.5
C8—C7—C4	130.4 (2)	H19A—C19—H19B	109.5
C9—C8—C7	105.5 (2)	C18—C19—H19C	109.5
C9—C8—H8	127.2	H19A—C19—H19C	109.5
C7—C8—H8	127.2	H19B—C19—H19C	109.5
N2—C9—C8	107.10 (19)	C18—C20—H20A	109.5
N2—C9—C10	122.7 (2)	C18—C20—H20B	109.5
C8—C9—C10	130.2 (2)	H20A—C20—H20B	109.5
O1—C10—O2	124.3 (2)	C18—C20—H20C	109.5
O1—C10—C9	123.5 (2)	H20A—C20—H20C	109.5
O2—C10—C9	112.2 (2)	H20B—C20—H20C	109.5
N2—C11—C12	113.02 (18)	C18—C21—H21A	109.5
N2—C11—H11A	109.0	C18—C21—H21B	109.5
C12—C11—H11A	109.0	H21A—C21—H21B	109.5
N2—C11—H11B	109.0	C18—C21—H21C	109.5
C12—C11—H11B	109.0	H21A—C21—H21C	109.5
H11A—C11—H11B	107.8	H21B—C21—H21C	109.5
C17—C12—C13	116.6 (2)	N2—N1—C7	105.68 (17)
C17—C12—C11	122.0 (2)	N1—N2—C9	111.31 (18)
C13—C12—C11	121.4 (2)	N1—N2—C11	118.34 (18)
C12—C13—C14	121.4 (2)	C9—N2—C11	130.25 (19)
C12—C13—H13	119.3	C10—O2—H2A	109.5
C14—C13—H13	119.3

C6—C1—C2—C3	−1.0 (4)	C11—C12—C13—C14	179.1 (3)
Cl1—C1—C2—C3	178.9 (2)	C12—C13—C14—C15	0.1 (5)
C1—C2—C3—C4	0.1 (4)	C13—C14—C15—C16	0.2 (4)
C2—C3—C4—C5	−0.1 (4)	C13—C14—C15—C18	179.3 (2)
C2—C3—C4—C7	179.9 (2)	C14—C15—C16—C17	0.0 (5)
C3—C4—C5—C6	0.9 (4)	C18—C15—C16—C17	−179.1 (3)
C7—C4—C5—C6	−179.1 (2)	C13—C12—C17—C16	0.8 (5)
C2—C1—C6—C5	1.8 (4)	C11—C12—C17—C16	−178.9 (3)
Cl1—C1—C6—C5	−178.16 (19)	C15—C16—C17—C12	−0.5 (5)
C4—C5—C6—C1	−1.7 (4)	C14—C15—C18—C21	−117.2 (3)
C3—C4—C7—N1	−179.6 (2)	C16—C15—C18—C21	61.9 (4)
C5—C4—C7—N1	0.4 (3)	C14—C15—C18—C20	122.0 (3)
C3—C4—C7—C8	−0.5 (3)	C16—C15—C18—C20	−58.9 (4)
C5—C4—C7—C8	179.5 (2)	C14—C15—C18—C19	1.6 (4)
N1—C7—C8—C9	−0.2 (2)	C16—C15—C18—C19	−179.3 (3)
C4—C7—C8—C9	−179.43 (19)	C8—C7—N1—N2	−0.2 (2)
C7—C8—C9—N2	0.6 (2)	C4—C7—N1—N2	179.10 (16)
C7—C8—C9—C10	178.73 (19)	C7—N1—N2—C9	0.6 (2)
N2—C9—C10—O1	−2.6 (3)	C7—N1—N2—C11	177.22 (17)
C8—C9—C10—O1	179.5 (2)	C8—C9—N2—N1	−0.7 (2)
N2—C9—C10—O2	177.59 (18)	C10—C9—N2—N1	−179.06 (17)
C8—C9—C10—O2	−0.3 (3)	C8—C9—N2—C11	−176.87 (19)
N2—C11—C12—C17	−131.2 (3)	C10—C9—N2—C11	4.8 (3)
N2—C11—C12—C13	49.1 (3)	C12—C11—N2—N1	−97.8 (2)
C17—C12—C13—C14	−0.6 (4)	C12—C11—N2—C9	78.1 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2A···O1ⁱ	0.82	1.81	2.624 (2)	177

Symmetry code: (i) −x+3, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	C₂₁H₂₁ClN₂O₂
M_r	368.85
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	6.6835 (1), 12.3218 (3), 12.6783 (3)
α, β, γ (°)	105.714 (2), 102.714 (1), 96.003 (2)
V (Å³)	965.32 (4)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.22
Crystal size (mm)	0.48 × 0.24 × 0.09

Data collection
Diffractometer	Bruker APEX II CCD area-detector
Absorption correction	Multi-scan (APEX2; Bruker, 2005)
T_min, T_max	0.905, 0.980
No. of measured, independent and observed [I > 2σ(I)] reflections	15167, 4403, 2700
R_int	0.026
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.050, 0.182, 0.92
No. of reflections	4403
No. of parameters	239
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.26, −0.17

Computer programs: APEX2 (Bruker, 2005), APEX2, SIR97 (Altomare et al., 1999), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1997), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2A···O1ⁱ	0.82	1.81	2.624 (2)	176.8

Symmetry code: (i) −x+3, −y+1, −z+1.

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