1-(4-Methyl­phen­yl)-5-oxo-2-phenyl­pyrrolidine-2-carboxamide–methanol (1/1)

Tamazyan, R.; Ayvazyan, A.; Martirosyan, A.; Harutyunyan, G.; Schinazi, R.

doi:10.1107/S1600536807043188

1-(4-Methylphenyl)-5-oxo-2-phenylpyrrolidine-2-carboxamide-methanol (1/1)

R. Tamazyan, A. Ayvazyan, A. Martirosyan, G. Harutyunyan and R. Schinazi

1-(4-Methylphenyl)-5-oxo-2-phenylpyrrolidine-2-carboxamide is a potential anti-human immunodeficiency virus type 1 (HIV-1) non-nucleoside reverse transcriptase inhibitor. In the title compound, C₁₈H₁₈N₂O₂·CH₄O, the pyrrolidine ring has a well expressed envelope conformation. The 1-(4-methylphenyl)-5-oxo-2-phenylpyrrolidine-2-carboxamide molecules are connected into infinite chains via hydrogen bonding with CH₃OH solvent molecules.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807043188/om2158sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807043188/om2158Isup2.hkl Contains datablock I

CCDC reference: 663733

checkCIF report

Key indicators

Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.002 Å
R factor = 0.043
wR factor = 0.110
Data-to-parameter ratio = 14.6

checkCIF/PLATON results

No syntax errors found



Datablock: I


Alert level C
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.57 Ratio
PLAT410_ALERT_2_C Short Intra H...H Contact  H2A    ..  H18     ..       1.96 Ang.
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........          2

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
PLAT793_ALERT_1_G Check the Absolute Configuration of C1     = ...          S

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

   3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 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 interest in the X-ray structural investigation of the title compound is stimulated by their potential HIV-1 RT inhibition properties (De Clercq, 1996). These compounds belong to a family of non-nucleoside reverse transcriptase inhibitors (NNRTIs). Related structures have been published by Karapetyan et al., 2002 and Tamazyan, et al., 2002.

A view of the molecule with our numbering scheme is depicted in Fig. 1. A l l intramolecular interatomic distances are in good agreement with their mean statistical values. The crystal structure consists of infinite chains along the [101] direction of crystal lattice. These chains molecules are formed by molecules of the title compound, C₁₈H₁₈N₂O₂, and solvent CH₃OH molecules via O2···H3o—O3···H2bⁱ—N2ⁱ hydrogen bonding (Fig.2).

Related literature top

For details of the synthesis, see: Martirosyan et al. (2000, 2004). For details of the pharmacological properties of compounds of this family, see: De Clercq (1996). For the crystal structures of some analogs of the title compound, see: Karapetyan et al. (2002) and Tamazyan et al. (2002).

Experimental top

The title compound was synthesized by the cycloalkylation of N1-cyano(phenyl)methyl-N1-(4-methylphenyl)-3-chloropropanamide under phase-transfer catalysis conditions and then by hydrolysis in concentrated sulfuric acid as it is described by Martirosyan et al., 2000, 2004. The compound as synthesized is a racemic mixture of molecules (2R and 2S)-1-(4-methylphenyl)-5-oxo-2-phenyltetrahydro-1H -2-pyrrolecarboxamide. The crystals were grown from a methanol solution of the compound.

Structure description top

Computing details top

Data collection: CAD-4 DATCOL (Enraf–Nonius, 1988); cell refinement: CAD-4 LS (Enraf–Nonius, 1988); data reduction: HELENA (Spek, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL-NT (Bruker, 2000) and ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXTL-NT (Bruker 2000).

Figures top

	Fig. 1. A view of the molecule with the atomic numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. H atoms are omitted for clarity.
	Fig. 2. The formation of infinite chain of molecules via hydrogen bonding. For clarity only H atoms participating in bonding are depicted. Symmetry codes: (i) 1/2 + x, 1/2 - y, -1/2 + z; (ii) 1 + x, y, -1 + z; (iii) 1.5 + x, 1/2 - y, -1.5 + z.

1-(4-methylphenyl)-5-oxo-2-phenylpyrrolidine-2-carboxamide –methanol (1/1) top

Crystal data top

C₁₈H₁₈N₂O₂·CH₄O	F(000) = 696
M_r = 326.39	D_x = 1.268 Mg m⁻³
Monoclinic, P2₁/n	Melting point: 96.0 K
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71073 Å
a = 7.9421 (16) Å	Cell parameters from 25 reflections
b = 20.761 (4) Å	θ = 10–15°
c = 10.403 (2) Å	µ = 0.09 mm⁻¹
β = 94.47 (3)°	T = 293 K
V = 1710.2 (6) Å³	Prism, colourless
Z = 4	0.35 × 0.28 × 0.23 mm

Data collection top

Enraf–Nonius CAD-4 diffractometer	R_int = 0.030
Radiation source: fine-focus sealed tube	θ_max = 28.0°, θ_min = 2.0°
Graphite monochromator	h = −10→10
θ/2θ scans	k = 0→27
8228 measured reflections	l = −13→13
4122 independent reflections	3 standard reflections every 180 min
2990 reflections with I > 2σ(I)	intensity decay: none

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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.110	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ²(F_o²) + (0.0491P)² + 0.3702P] where P = (F_o² + 2F_c²)/3
4122 reflections	(Δ/σ)_max < 0.001
283 parameters	Δρ_max = 0.22 e Å⁻³
0 restraints	Δρ_min = −0.22 e Å⁻³

Crystal data top

C₁₈H₁₈N₂O₂·CH₄O	V = 1710.2 (6) Å³
M_r = 326.39	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 7.9421 (16) Å	µ = 0.09 mm⁻¹
b = 20.761 (4) Å	T = 293 K
c = 10.403 (2) Å	0.35 × 0.28 × 0.23 mm
β = 94.47 (3)°

Data collection top

Enraf–Nonius CAD-4 diffractometer	R_int = 0.030
8228 measured reflections	3 standard reflections every 180 min
4122 independent reflections	intensity decay: none
2990 reflections with I > 2σ(I)

Refinement top

R[F² > 2σ(F²)] = 0.043	0 restraints
wR(F²) = 0.110	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	Δρ_max = 0.22 e Å⁻³
4122 reflections	Δρ_min = −0.22 e Å⁻³
283 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	0.09584 (16)	0.29428 (7)	0.70924 (12)	0.0236 (3)
N1	0.25160 (13)	0.28492 (5)	0.64212 (10)	0.0241 (2)
O1	0.46719 (12)	0.21200 (5)	0.63351 (11)	0.0363 (3)
C2	0.13038 (19)	0.24956 (8)	0.82787 (13)	0.0304 (3)
H2A	0.192 (2)	0.2739 (8)	0.8979 (16)	0.036 (4)*
H2B	0.024 (2)	0.2325 (8)	0.8585 (16)	0.041 (5)*
H2NA	−0.297 (2)	0.2556 (9)	0.6374 (18)	0.046 (5)*
H2NB	−0.222 (2)	0.3044 (9)	0.7367 (18)	0.043 (5)*
N2	−0.20793 (15)	0.27778 (7)	0.66831 (13)	0.0310 (3)
O2	−0.03691 (12)	0.22527 (5)	0.54227 (10)	0.0348 (3)
C3	0.24343 (19)	0.19719 (8)	0.77964 (15)	0.0326 (3)
H3A	0.320 (2)	0.1794 (9)	0.8450 (17)	0.042 (5)*
H3B	0.175 (2)	0.1615 (9)	0.7353 (17)	0.043 (5)*
C4	0.33748 (16)	0.23050 (7)	0.67804 (13)	0.0265 (3)
C5	0.30378 (16)	0.32782 (7)	0.54477 (13)	0.0242 (3)
C6	0.43874 (17)	0.36892 (7)	0.57445 (15)	0.0305 (3)
H6	0.493 (2)	0.3684 (8)	0.6611 (16)	0.033 (4)*
C7	0.4904 (2)	0.41026 (8)	0.48041 (16)	0.0362 (3)
H7	0.582 (2)	0.4392 (9)	0.4998 (17)	0.046 (5)*
C8	0.4083 (2)	0.41248 (7)	0.35797 (15)	0.0351 (3)
C9	0.4635 (3)	0.45847 (9)	0.25726 (19)	0.0544 (5)
H9A	0.4045	0.4986	0.2633	0.082*
H9B	0.4384	0.4403	0.1731	0.082*
H9C	0.5829	0.4658	0.2712	0.082*
C10	0.2733 (2)	0.37093 (8)	0.33059 (15)	0.0343 (3)
H10	0.215 (2)	0.3694 (8)	0.2450 (18)	0.042 (5)*
C11	0.22140 (18)	0.32872 (7)	0.42227 (14)	0.0292 (3)
H11	0.132 (2)	0.2979 (8)	0.4011 (16)	0.035 (4)*
C12	−0.05730 (16)	0.26366 (7)	0.62983 (12)	0.0243 (3)
C13	0.07342 (17)	0.36569 (7)	0.73870 (14)	0.0286 (3)
C14	−0.0165 (2)	0.40578 (8)	0.65111 (16)	0.0377 (4)
H14	−0.067 (2)	0.3876 (9)	0.5741 (19)	0.050 (5)*
C15	−0.0277 (2)	0.47155 (9)	0.6730 (2)	0.0475 (4)
H15	−0.092 (3)	0.4978 (11)	0.612 (2)	0.061 (6)*
C16	0.0504 (3)	0.49807 (9)	0.7833 (2)	0.0546 (5)
H16	0.042 (3)	0.5427 (11)	0.799 (2)	0.062 (6)*
C17	0.1403 (3)	0.45928 (10)	0.8694 (2)	0.0606 (6)
H17	0.197 (3)	0.4758 (12)	0.947 (2)	0.080 (7)*
C18	0.1530 (2)	0.39355 (9)	0.84826 (18)	0.0455 (4)
H18	0.224 (3)	0.3675 (10)	0.908 (2)	0.060 (6)*
O3	0.15641 (18)	0.15833 (7)	0.38084 (12)	0.0523 (4)
H3O	0.099 (3)	0.1805 (12)	0.430 (2)	0.078 (8)*
C19	0.2047 (3)	0.10171 (9)	0.44502 (18)	0.0544 (5)
H19A	0.2758	0.1118	0.5212	0.082*
H19B	0.2654	0.0749	0.3894	0.082*
H19C	0.1060	0.0793	0.4688	0.082*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0186 (6)	0.0312 (7)	0.0213 (6)	−0.0009 (5)	0.0034 (5)	−0.0005 (5)
N1	0.0175 (5)	0.0297 (6)	0.0253 (5)	0.0008 (4)	0.0037 (4)	0.0033 (5)
O1	0.0213 (5)	0.0366 (6)	0.0515 (6)	0.0041 (4)	0.0057 (4)	0.0027 (5)
C2	0.0288 (7)	0.0387 (8)	0.0235 (7)	−0.0044 (6)	0.0001 (6)	0.0048 (6)
N2	0.0194 (5)	0.0407 (7)	0.0334 (6)	−0.0021 (5)	0.0045 (5)	−0.0081 (6)
O2	0.0247 (5)	0.0455 (6)	0.0341 (5)	0.0002 (4)	0.0018 (4)	−0.0143 (5)
C3	0.0267 (7)	0.0361 (8)	0.0343 (8)	−0.0025 (6)	−0.0015 (6)	0.0106 (7)
C4	0.0192 (6)	0.0279 (7)	0.0318 (7)	−0.0024 (5)	−0.0028 (5)	0.0008 (6)
C5	0.0200 (6)	0.0265 (7)	0.0269 (6)	0.0034 (5)	0.0062 (5)	0.0006 (5)
C6	0.0264 (7)	0.0331 (8)	0.0321 (7)	−0.0014 (6)	0.0024 (6)	0.0010 (6)
C7	0.0317 (8)	0.0320 (8)	0.0459 (9)	−0.0056 (6)	0.0093 (7)	0.0032 (7)
C8	0.0388 (8)	0.0299 (8)	0.0386 (8)	0.0081 (6)	0.0166 (6)	0.0073 (6)
C9	0.0663 (12)	0.0456 (10)	0.0547 (11)	0.0038 (9)	0.0260 (9)	0.0187 (9)
C10	0.0392 (8)	0.0365 (8)	0.0275 (7)	0.0075 (7)	0.0042 (6)	0.0039 (6)
C11	0.0267 (7)	0.0323 (7)	0.0287 (7)	0.0005 (6)	0.0022 (5)	0.0005 (6)
C12	0.0210 (6)	0.0291 (7)	0.0230 (6)	0.0006 (5)	0.0021 (5)	0.0020 (5)
C13	0.0224 (6)	0.0324 (7)	0.0322 (7)	−0.0017 (5)	0.0093 (5)	−0.0035 (6)
C14	0.0421 (9)	0.0360 (8)	0.0359 (8)	0.0037 (7)	0.0083 (7)	−0.0008 (7)
C15	0.0505 (10)	0.0371 (9)	0.0570 (11)	0.0067 (8)	0.0173 (9)	0.0043 (8)
C16	0.0558 (11)	0.0317 (9)	0.0786 (14)	−0.0040 (8)	0.0191 (10)	−0.0131 (9)
C17	0.0626 (13)	0.0473 (12)	0.0702 (14)	−0.0063 (10)	−0.0055 (11)	−0.0251 (10)
C18	0.0433 (9)	0.0416 (10)	0.0501 (10)	−0.0011 (8)	−0.0055 (8)	−0.0125 (8)
O3	0.0678 (9)	0.0518 (8)	0.0404 (7)	0.0186 (7)	0.0246 (6)	0.0102 (6)
C19	0.0786 (14)	0.0398 (10)	0.0466 (10)	0.0067 (9)	0.0168 (9)	0.0003 (8)

Geometric parameters (Å, º) top

C1—N1	1.4800 (16)	C8—C9	1.508 (2)
C1—C13	1.527 (2)	C9—H9A	0.9600
C1—C2	1.5517 (19)	C9—H9B	0.9600
C1—C12	1.5522 (18)	C9—H9C	0.9600
N1—C4	1.3571 (17)	C10—C11	1.382 (2)
N1—C5	1.4338 (17)	C10—H10	0.973 (18)
O1—C4	1.2238 (17)	C11—H11	0.967 (17)
C2—C3	1.520 (2)	C13—C18	1.386 (2)
C2—H2A	0.985 (17)	C13—C14	1.390 (2)
C2—H2B	0.995 (18)	C14—C15	1.388 (2)
N2—C12	1.3236 (17)	C14—H14	0.947 (19)
N2—H2NA	0.88 (2)	C15—C16	1.376 (3)
N2—H2NB	0.915 (19)	C15—H15	0.95 (2)
O2—C12	1.2305 (16)	C16—C17	1.365 (3)
C3—C4	1.509 (2)	C16—H16	0.94 (2)
C3—H3A	0.953 (18)	C17—C18	1.387 (3)
C3—H3B	1.010 (18)	C17—H17	0.95 (2)
C5—C6	1.386 (2)	C18—H18	0.97 (2)
C5—C11	1.387 (2)	O3—C19	1.391 (2)
C6—C7	1.388 (2)	O3—H3O	0.84 (3)
C6—H6	0.970 (17)	C19—H19A	0.9600
C7—C8	1.386 (2)	C19—H19B	0.9600
C7—H7	0.954 (19)	C19—H19C	0.9600
C8—C10	1.388 (2)

N1—C1—C13	109.70 (10)	C8—C9—H9B	109.5
N1—C1—C2	101.20 (10)	H9A—C9—H9B	109.5
C13—C1—C2	115.94 (11)	C8—C9—H9C	109.5
N1—C1—C12	110.13 (10)	H9A—C9—H9C	109.5
C13—C1—C12	113.94 (11)	H9B—C9—H9C	109.5
C2—C1—C12	105.12 (11)	C11—C10—C8	121.32 (15)
C4—N1—C5	123.02 (11)	C11—C10—H10	117.6 (11)
C4—N1—C1	113.58 (11)	C8—C10—H10	121.0 (10)
C5—N1—C1	123.36 (11)	C10—C11—C5	119.88 (14)
C3—C2—C1	103.77 (11)	C10—C11—H11	121.0 (10)
C3—C2—H2A	109.7 (10)	C5—C11—H11	119.0 (10)
C1—C2—H2A	109.2 (10)	O2—C12—N2	122.78 (13)
C3—C2—H2B	113.0 (10)	O2—C12—C1	121.09 (12)
C1—C2—H2B	111.5 (10)	N2—C12—C1	115.95 (12)
H2A—C2—H2B	109.5 (14)	C18—C13—C14	117.86 (15)
C12—N2—H2NA	119.4 (12)	C18—C13—C1	121.16 (14)
C12—N2—H2NB	122.6 (11)	C14—C13—C1	120.78 (13)
H2NA—N2—H2NB	117.0 (17)	C15—C14—C13	121.18 (17)
C4—C3—C2	103.93 (12)	C15—C14—H14	120.1 (12)
C4—C3—H3A	110.7 (11)	C13—C14—H14	118.7 (12)
C2—C3—H3A	113.8 (11)	C16—C15—C14	120.00 (19)
C4—C3—H3B	107.2 (10)	C16—C15—H15	120.7 (13)
C2—C3—H3B	111.2 (10)	C14—C15—H15	119.3 (13)
H3A—C3—H3B	109.6 (15)	C17—C16—C15	119.35 (18)
O1—C4—N1	125.23 (13)	C17—C16—H16	120.4 (13)
O1—C4—C3	126.77 (13)	C15—C16—H16	120.2 (13)
N1—C4—C3	107.99 (12)	C16—C17—C18	121.15 (19)
C6—C5—C11	119.85 (13)	C16—C17—H17	122.0 (15)
C6—C5—N1	119.09 (12)	C18—C17—H17	116.8 (15)
C11—C5—N1	121.06 (12)	C13—C18—C17	120.46 (19)
C5—C6—C7	119.35 (14)	C13—C18—H18	119.8 (12)
C5—C6—H6	118.8 (10)	C17—C18—H18	119.6 (12)
C7—C6—H6	121.8 (10)	C19—O3—H3O	108.3 (17)
C8—C7—C6	121.63 (15)	O3—C19—H19A	109.5
C8—C7—H7	118.1 (11)	O3—C19—H19B	109.5
C6—C7—H7	120.2 (11)	H19A—C19—H19B	109.5
C7—C8—C10	117.95 (14)	O3—C19—H19C	109.5
C7—C8—C9	121.19 (16)	H19A—C19—H19C	109.5
C10—C8—C9	120.85 (16)	H19B—C19—H19C	109.5
C8—C9—H9A	109.5

C13—C1—N1—C4	142.23 (12)	C7—C8—C10—C11	0.2 (2)
C2—C1—N1—C4	19.24 (14)	C9—C8—C10—C11	−179.83 (15)
C12—C1—N1—C4	−91.60 (13)	C8—C10—C11—C5	0.6 (2)
C13—C1—N1—C5	−40.05 (16)	C6—C5—C11—C10	−0.5 (2)
C2—C1—N1—C5	−163.05 (12)	N1—C5—C11—C10	179.43 (13)
C12—C1—N1—C5	86.11 (15)	N1—C1—C12—O2	15.40 (18)
N1—C1—C2—C3	−29.06 (13)	C13—C1—C12—O2	139.14 (13)
C13—C1—C2—C3	−147.64 (12)	C2—C1—C12—O2	−92.85 (15)
C12—C1—C2—C3	85.58 (13)	N1—C1—C12—N2	−169.31 (12)
C1—C2—C3—C4	29.29 (14)	C13—C1—C12—N2	−45.57 (16)
C5—N1—C4—O1	0.5 (2)	C2—C1—C12—N2	82.44 (14)
C1—N1—C4—O1	178.18 (13)	N1—C1—C13—C18	−84.59 (16)
C5—N1—C4—C3	−178.68 (12)	C2—C1—C13—C18	29.21 (19)
C1—N1—C4—C3	−0.96 (15)	C12—C1—C13—C18	151.44 (14)
C2—C3—C4—O1	162.53 (14)	N1—C1—C13—C14	90.18 (15)
C2—C3—C4—N1	−18.35 (15)	C2—C1—C13—C14	−156.02 (13)
C4—N1—C5—C6	−76.02 (17)	C12—C1—C13—C14	−33.79 (17)
C1—N1—C5—C6	106.48 (15)	C18—C13—C14—C15	−0.6 (2)
C4—N1—C5—C11	104.04 (15)	C1—C13—C14—C15	−175.51 (14)
C1—N1—C5—C11	−73.46 (17)	C13—C14—C15—C16	−0.3 (3)
C11—C5—C6—C7	−0.4 (2)	C14—C15—C16—C17	0.9 (3)
N1—C5—C6—C7	179.62 (13)	C15—C16—C17—C18	−0.6 (3)
C5—C6—C7—C8	1.3 (2)	C14—C13—C18—C17	0.9 (3)
C6—C7—C8—C10	−1.2 (2)	C1—C13—C18—C17	175.77 (16)
C6—C7—C8—C9	178.85 (15)	C16—C17—C18—C13	−0.3 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3o···O2	0.84 (2)	1.90 (2)	2.741 (2)	176 (2)
N2ⁱ—H2nBⁱ···O3	0.91 (2)	2.00 (2)	2.860 (2)	156 (2)

Symmetry code: (i) x+1/2, −y+1/2, z−1/2.

Experimental details

Crystal data
Chemical formula	C₁₈H₁₈N₂O₂·CH₄O
M_r	326.39
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	293
a, b, c (Å)	7.9421 (16), 20.761 (4), 10.403 (2)
β (°)	94.47 (3)
V (Å³)	1710.2 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.35 × 0.28 × 0.23

Data collection
Diffractometer	Enraf–Nonius CAD-4
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	8228, 4122, 2990
R_int	0.030
(sin θ/λ)_max (Å⁻¹)	0.660

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.043, 0.110, 1.02
No. of reflections	4122
No. of parameters	283
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.22, −0.22

Computer programs: CAD-4 DATCOL (Enraf–Nonius, 1988), CAD-4 LS (Enraf–Nonius, 1988), HELENA (Spek, 1997), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL-NT (Bruker, 2000) and ORTEPII (Johnson, 1976), SHELXTL-NT (Bruker 2000).