1-Methyl-5-(4-methyl­benzo­yl)-4-(4-methyl­phen­yl)pyrimidine-2(1H)-thione

Dinçer, M.; Koca, İ.; Yıldırım, İ.; Özdemir, N.

doi:10.1107/S1600536807057923

1-Methyl-5-(4-methylbenzoyl)-4-(4-methylphenyl)pyrimidine-2(1H)-thione

M. Dinçer, İ. Koca, İ. Yıldırım and N. Özdemir

The title compound, C₂₀H₁₈N₂OS, contains three rings that are not coplanar. The benzene rings make dihedral angles of 31.37 (8) and 68.84 (5)° with the pyrimidine ring, while the dihedral angle between the two benzene rings is 76.70 (5)°. The structure is stabilized by intermolecular C—H

O hydrogen bonds, resulting in the formation of molecular chains along the [010] direction.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807057923/zl2088sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807057923/zl2088Isup2.hkl Contains datablock I

CCDC reference: 673000

checkCIF report

Key indicators

Single-crystal X-ray study
T = 296 K
Mean (C-C) = 0.003 Å
R factor = 0.039
wR factor = 0.107
Data-to-parameter ratio = 15.0

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size .......       0.61 mm
PLAT230_ALERT_2_C Hirshfeld Test Diff for    S2     -   C2      ..       5.16 su

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

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

Comment top

In general, pyrimidines have found much interest for their widespread potential biological activities (Kleemann & Engel, 1982) and medicinal applications, thus their chemistry has been investigated extensively (Brown, 1984, 1985; Lomis et al., 1988). In particular, various analogues of pyrimidine-thiones possess effective antibacterial, antifungal, antiviral, anti-AIDS, insecticidal and miticidal activities (De Clerq & Walker, 1985). Furthermore many condensed heterocyclic systems, especially when linked to a pyrimidine ring, play an important role as analgesic (Perrissin et al., 1988), antihypertensive (Cannito et al., 1990), antipyretic (Smith & Kan, 1964), and antiinflammatory drugs (Vega et al., 1990), also as pesticides (Tetsuo et al., 1987), herbicides (Chakaravorty et al., 1992), and plant growth regulators (Shishoo & Jain, 1992). In view of these important properties, we have undertaken the X-ray diffraction study of the title compound.

The structure of the title compound is shown in Fig. 1. The structure contains one central pyrimidine ring (N1/N3/C2/C4—C6) with a methyl substituent at N1, an S substituent at C2, a p-tolyl group (C41—C47) at C4 and a methylbenzoyl group (O5/C51—C58) at C5. The plane of the pyrimidine ring makes dihedral angles of 31.37 (8) and 68.84 (5)° with the (C41—C46) and (C52—C57) phenyl rings, respectively. The pyrimidine ring is planar with a maximum deviation of 0.0776 (12) Å for atom C2. The interatomic distances and angles show no anomalies.

The molecular structure of the title compound contains no significant intramolecular interactions. In the construction of the intermolecular connections, 2₁ screw symmetry-related molecules, which form pairs of neighbouring molecules translated linearly along the b axis of the unit cell, play an active bridging role. Atom C47 acts as a hydrogen-bond donor, via atom H47B, to atom O5 at (2 - x, -1/2 + y, 1/2 - z). Extension of this hydrogen-bonding interaction along b results in the formation of molecular chains along the [010] direction (Fig. 2).

Related literature top

The starting material was prepared in a manner similar to that described by Ziegler et al. (1967). Biological activities of pyrimidines and pyrimidinethiones are described by Brown (1984, 1985), Cannito et al. (1990), Chakaravorty et al. (1992), De Clerq & Walker (1985), Kleemann & Engel (1982), Lomis et al. (1988), Perrissin et al. (1988), Shishoo & Jain (1992), Smith & Kan (1964), Tetsuo et al. (1987) and Vega et al. (1990).

Experimental top

An equimolar mixture of 4-(4-methylbenzoyl)-5-(4-methylphenyl)-2,3-dihydro-2,3-furandione (0.50 g, 1.63 mmol), easily obtained from oxalyl chloride and 1,3-bis(4-methylphenyl)propane-1,3-dione, in a similar way as described by Ziegler et al. (1967), and N-methylthiourea (0.15 g, 1.63 mmol) were refluxed in 30 ml boiling benzene for 3 h. After the evaporation of the solvent, the oily residue was treated with dry diethylether to give a yellow precipitate, which was filtered off and recrystallized from acetic acid (yield: 0.35 g, 64%; m.p. 483 K). IR (KBr, ν, cm^-1): 3040–2840 (w, aromatic and aliphatic C—H), 1650 (s, C═O), 1603 s, 1567 w, 1514 s, 1492 m (C≐C, C≐N, phenyl and aromatic rings), 1185 (m, C═S); ¹H NMR (300 MHz, CDCl₃, p.p.m.): δ 8.16 (s, 1H at C-6), 7.56–6.99 (m, 8H, Ar—H), 3.97 (s, 3H, N—CH₃), 2.31, 2.24 (two s, 6H, Ar—CH₃). Analysis calculated for C₂₀H₁₈N2OS: C 71.83, H 5.42, N 8.38, S 9.59%; found: C 71.80, H 5.47, N 8.18, S 9.60%.

Computing details top

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA (Stoe & Cie, 2002); data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON (Spek, 2003).

Figures top

	Fig. 1. : An ORTEP-3 (Farrugia, 1997) drawing of the title compound, showing the atomic numbering scheme. Displacement ellipsoids are drawn at the 40% probability level.
	Fig. 2. : The molecular packing of the title compound, viewed along the c axis. Dashed lines show the C—H···O interactions.

1-Methyl-5-(4-methylbenzoyl)-4-(4-methylphenyl)pyrimidine-2(1H)-thione top

Crystal data top

C₂₀H₁₈N₂OS	F(000) = 704
M_r = 334.42	D_x = 1.300 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 20480 reflections
a = 5.8203 (5) Å	θ = 1.7–27.9°
b = 15.6178 (10) Å	µ = 0.20 mm⁻¹
c = 19.4161 (16) Å	T = 296 K
β = 104.466 (6)°	Prismatic rod, colorless
V = 1709.0 (2) Å³	0.61 × 0.35 × 0.20 mm
Z = 4

Data collection top

Stoe IPDSII diffractometer	3294 independent reflections
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus	2225 reflections with I > 2σ(I)
Plane graphite monochromator	R_int = 0.043
Detector resolution: 6.67 pixels mm^-1	θ_max = 26.0°, θ_min = 1.7°
w scans	h = −7→6
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	k = −19→19
T_min = 0.923, T_max = 0.978	l = −23→23
14819 measured reflections

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.107	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.0613P)²] where P = (F_o² + 2F_c²)/3
3294 reflections	(Δ/σ)_max = 0.001
220 parameters	Δρ_max = 0.17 e Å⁻³
0 restraints	Δρ_min = −0.27 e Å⁻³

Crystal data top

C₂₀H₁₈N₂OS	V = 1709.0 (2) Å³
M_r = 334.42	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 5.8203 (5) Å	µ = 0.20 mm⁻¹
b = 15.6178 (10) Å	T = 296 K
c = 19.4161 (16) Å	0.61 × 0.35 × 0.20 mm
β = 104.466 (6)°

Data collection top

Stoe IPDSII diffractometer	3294 independent reflections
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	2225 reflections with I > 2σ(I)
T_min = 0.923, T_max = 0.978	R_int = 0.043
14819 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.039	0 restraints
wR(F²) = 0.107	H-atom parameters constrained
S = 1.01	Δρ_max = 0.17 e Å⁻³
3294 reflections	Δρ_min = −0.27 e Å⁻³
220 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
S2	0.46693 (13)	0.34236 (4)	0.50064 (3)	0.0795 (2)
O5	0.6981 (3)	0.54459 (8)	0.24409 (7)	0.0582 (3)
N1	0.2814 (3)	0.44445 (10)	0.39131 (7)	0.0513 (4)
N3	0.5736 (3)	0.34751 (9)	0.37627 (8)	0.0522 (4)
C1	0.1086 (4)	0.47291 (14)	0.43011 (11)	0.0665 (6)
H1A	0.1881	0.5061	0.4707	0.100*
H1B	0.0355	0.4239	0.4456	0.100*
H1C	−0.0108	0.5074	0.3994	0.100*
C2	0.4422 (3)	0.37950 (12)	0.41885 (9)	0.0518 (4)
C4	0.5771 (3)	0.38456 (11)	0.31569 (9)	0.0450 (4)
C5	0.4461 (3)	0.46083 (11)	0.29287 (8)	0.0447 (4)
C6	0.2926 (3)	0.48546 (12)	0.33108 (9)	0.0502 (4)
H6	0.1924	0.5317	0.3155	0.060*
C41	0.7127 (3)	0.34048 (10)	0.27081 (9)	0.0464 (4)
C42	0.6388 (4)	0.34305 (11)	0.19719 (9)	0.0525 (5)
H42	0.5051	0.3747	0.1754	0.063*
C43	0.7608 (4)	0.29933 (12)	0.15594 (10)	0.0555 (5)
H43	0.7066	0.3014	0.1067	0.067*
C44	0.9619 (4)	0.25246 (11)	0.18617 (10)	0.0531 (4)
C45	1.0344 (4)	0.24938 (12)	0.25993 (10)	0.0598 (5)
H45	1.1682	0.2176	0.2815	0.072*
C46	0.9127 (3)	0.29225 (12)	0.30189 (10)	0.0539 (5)
H46	0.9646	0.2889	0.3512	0.065*
C47	1.0966 (4)	0.20643 (14)	0.14034 (12)	0.0702 (6)
H47A	0.9894	0.1908	0.0960	0.105*
H47B	1.1683	0.1558	0.1644	0.105*
H47C	1.2177	0.2434	0.1314	0.105*
C51	0.4959 (3)	0.51927 (10)	0.23664 (9)	0.0450 (4)
C52	0.2996 (3)	0.54438 (10)	0.17599 (8)	0.0447 (4)
C53	0.0838 (4)	0.50202 (11)	0.16035 (9)	0.0514 (4)
H53	0.0575	0.4584	0.1901	0.062*
C54	−0.0921 (4)	0.52392 (13)	0.10124 (10)	0.0581 (5)
H54	−0.2355	0.4945	0.0914	0.070*
C55	−0.0594 (4)	0.58882 (13)	0.05625 (9)	0.0566 (5)
C56	0.1566 (4)	0.63170 (13)	0.07211 (10)	0.0624 (5)
H56	0.1813	0.6759	0.0427	0.075*
C57	0.3338 (4)	0.60988 (12)	0.13040 (10)	0.0559 (5)
H57	0.4780	0.6388	0.1397	0.067*
C58	−0.2554 (5)	0.61164 (16)	−0.00808 (11)	0.0796 (7)
H58A	−0.3507	0.6566	0.0041	0.119*
H58B	−0.3525	0.5622	−0.0235	0.119*
H58C	−0.1875	0.6307	−0.0457	0.119*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S2	0.0944 (5)	0.0918 (4)	0.0535 (3)	−0.0007 (3)	0.0208 (3)	0.0217 (3)
O5	0.0490 (9)	0.0646 (8)	0.0613 (8)	−0.0083 (7)	0.0141 (6)	0.0010 (6)
N1	0.0519 (10)	0.0569 (9)	0.0478 (8)	−0.0017 (7)	0.0174 (7)	−0.0001 (6)
N3	0.0521 (10)	0.0539 (9)	0.0485 (8)	0.0008 (7)	0.0087 (7)	0.0058 (6)
C1	0.0691 (16)	0.0777 (14)	0.0615 (11)	0.0007 (11)	0.0330 (10)	−0.0042 (10)
C2	0.0502 (12)	0.0544 (10)	0.0494 (9)	−0.0073 (9)	0.0100 (8)	0.0030 (8)
C4	0.0392 (11)	0.0486 (9)	0.0444 (8)	−0.0035 (7)	0.0048 (7)	0.0002 (7)
C5	0.0430 (11)	0.0472 (9)	0.0428 (8)	0.0001 (8)	0.0088 (7)	0.0012 (7)
C6	0.0512 (12)	0.0528 (10)	0.0468 (9)	0.0026 (8)	0.0124 (8)	0.0034 (7)
C41	0.0449 (11)	0.0437 (9)	0.0494 (9)	−0.0019 (8)	0.0095 (7)	0.0007 (7)
C42	0.0497 (12)	0.0505 (10)	0.0518 (9)	0.0060 (8)	0.0020 (8)	−0.0040 (8)
C43	0.0617 (14)	0.0518 (10)	0.0500 (9)	0.0036 (9)	0.0084 (9)	−0.0049 (8)
C44	0.0531 (12)	0.0418 (9)	0.0668 (11)	−0.0025 (8)	0.0193 (9)	−0.0019 (8)
C45	0.0528 (13)	0.0585 (11)	0.0672 (12)	0.0133 (9)	0.0135 (9)	0.0079 (9)
C46	0.0517 (12)	0.0552 (11)	0.0521 (10)	0.0057 (9)	0.0078 (8)	0.0062 (8)
C47	0.0744 (17)	0.0586 (13)	0.0851 (14)	0.0067 (11)	0.0342 (12)	−0.0048 (10)
C51	0.0461 (12)	0.0441 (9)	0.0466 (9)	−0.0016 (8)	0.0151 (7)	−0.0043 (7)
C52	0.0495 (12)	0.0422 (9)	0.0442 (9)	0.0031 (8)	0.0151 (7)	0.0009 (7)
C53	0.0505 (13)	0.0534 (10)	0.0508 (9)	−0.0005 (8)	0.0138 (8)	0.0097 (8)
C54	0.0477 (13)	0.0680 (12)	0.0568 (10)	0.0016 (9)	0.0094 (8)	0.0054 (9)
C55	0.0635 (14)	0.0570 (11)	0.0481 (9)	0.0169 (10)	0.0118 (9)	0.0028 (8)
C56	0.0816 (17)	0.0527 (11)	0.0536 (11)	0.0070 (11)	0.0181 (10)	0.0144 (8)
C57	0.0636 (14)	0.0494 (10)	0.0560 (10)	−0.0073 (9)	0.0174 (9)	0.0033 (8)
C58	0.0835 (18)	0.0877 (16)	0.0610 (12)	0.0265 (13)	0.0054 (11)	0.0140 (11)

Geometric parameters (Å, º) top

S2—C2	1.6628 (18)	C44—C47	1.507 (3)
O5—C51	1.215 (2)	C45—C46	1.379 (3)
N1—C6	1.349 (2)	C45—H45	0.9300
N1—C2	1.393 (2)	C46—H46	0.9300
N1—C1	1.468 (2)	C47—H47A	0.9600
N3—C4	1.316 (2)	C47—H47B	0.9600
N3—C2	1.354 (2)	C47—H47C	0.9600
C1—H1A	0.9600	C51—C52	1.474 (2)
C1—H1B	0.9600	C52—C53	1.384 (3)
C1—H1C	0.9600	C52—C57	1.399 (2)
C4—C5	1.424 (2)	C53—C54	1.377 (3)
C4—C41	1.483 (2)	C53—H53	0.9300
C5—C6	1.352 (2)	C54—C55	1.382 (3)
C5—C51	1.506 (2)	C54—H54	0.9300
C6—H6	0.9300	C55—C56	1.390 (3)
C41—C42	1.387 (2)	C55—C58	1.509 (3)
C41—C46	1.391 (3)	C56—C57	1.370 (3)
C42—C43	1.377 (3)	C56—H56	0.9300
C42—H42	0.9300	C57—H57	0.9300
C43—C44	1.381 (3)	C58—H58A	0.9600
C43—H43	0.9300	C58—H58B	0.9600
C44—C45	1.389 (3)	C58—H58C	0.9600

C6—N1—C2	120.33 (16)	C45—C46—C41	120.27 (17)
C6—N1—C1	119.26 (16)	C45—C46—H46	119.9
C2—N1—C1	120.28 (15)	C41—C46—H46	119.9
C4—N3—C2	121.39 (16)	C44—C47—H47A	109.5
N1—C1—H1A	109.5	C44—C47—H47B	109.5
N1—C1—H1B	109.5	H47A—C47—H47B	109.5
H1A—C1—H1B	109.5	C44—C47—H47C	109.5
N1—C1—H1C	109.5	H47A—C47—H47C	109.5
H1A—C1—H1C	109.5	H47B—C47—H47C	109.5
H1B—C1—H1C	109.5	O5—C51—C52	122.87 (16)
N3—C2—N1	117.52 (15)	O5—C51—C5	117.83 (16)
N3—C2—S2	121.80 (15)	C52—C51—C5	119.29 (16)
N1—C2—S2	120.67 (14)	C53—C52—C57	118.39 (16)
N3—C4—C5	121.29 (16)	C53—C52—C51	121.85 (15)
N3—C4—C41	116.78 (15)	C57—C52—C51	119.68 (17)
C5—C4—C41	121.84 (15)	C54—C53—C52	120.61 (17)
C6—C5—C4	116.30 (15)	C54—C53—H53	119.7
C6—C5—C51	119.91 (15)	C52—C53—H53	119.7
C4—C5—C51	123.21 (16)	C53—C54—C55	121.2 (2)
N1—C6—C5	121.48 (17)	C53—C54—H54	119.4
N1—C6—H6	119.3	C55—C54—H54	119.4
C5—C6—H6	119.3	C54—C55—C56	118.24 (17)
C42—C41—C46	118.24 (17)	C54—C55—C58	120.1 (2)
C42—C41—C4	121.24 (16)	C56—C55—C58	121.65 (19)
C46—C41—C4	120.46 (16)	C57—C56—C55	121.07 (18)
C43—C42—C41	120.87 (18)	C57—C56—H56	119.5
C43—C42—H42	119.6	C55—C56—H56	119.5
C41—C42—H42	119.6	C56—C57—C52	120.49 (19)
C42—C43—C44	121.41 (17)	C56—C57—H57	119.8
C42—C43—H43	119.3	C52—C57—H57	119.8
C44—C43—H43	119.3	C55—C58—H58A	109.5
C43—C44—C45	117.60 (18)	C55—C58—H58B	109.5
C43—C44—C47	120.84 (18)	H58A—C58—H58B	109.5
C45—C44—C47	121.56 (19)	C55—C58—H58C	109.5
C46—C45—C44	121.58 (18)	H58A—C58—H58C	109.5
C46—C45—H45	119.2	H58B—C58—H58C	109.5
C44—C45—H45	119.2

C4—N3—C2—N1	10.2 (3)	C42—C43—C44—C47	−178.71 (19)
C4—N3—C2—S2	−170.65 (14)	C43—C44—C45—C46	−0.8 (3)
C6—N1—C2—N3	−13.5 (3)	C47—C44—C45—C46	179.28 (19)
C1—N1—C2—N3	170.69 (17)	C44—C45—C46—C41	−0.3 (3)
C6—N1—C2—S2	167.39 (14)	C42—C41—C46—C45	0.8 (3)
C1—N1—C2—S2	−8.4 (2)	C4—C41—C46—C45	178.15 (17)
C2—N3—C4—C5	1.1 (3)	C6—C5—C51—O5	118.22 (19)
C2—N3—C4—C41	−175.58 (16)	C4—C5—C51—O5	−52.7 (2)
N3—C4—C5—C6	−9.4 (3)	C6—C5—C51—C52	−60.9 (2)
C41—C4—C5—C6	167.09 (16)	C4—C5—C51—C52	128.16 (18)
N3—C4—C5—C51	161.81 (16)	O5—C51—C52—C53	166.43 (17)
C41—C4—C5—C51	−21.7 (3)	C5—C51—C52—C53	−14.5 (2)
C2—N1—C6—C5	5.2 (3)	O5—C51—C52—C57	−10.3 (2)
C1—N1—C6—C5	−178.97 (18)	C5—C51—C52—C57	168.79 (15)
C4—C5—C6—N1	6.1 (3)	C57—C52—C53—C54	0.1 (3)
C51—C5—C6—N1	−165.48 (16)	C51—C52—C53—C54	−176.60 (17)
N3—C4—C41—C42	145.70 (18)	C52—C53—C54—C55	−0.4 (3)
C5—C4—C41—C42	−31.0 (3)	C53—C54—C55—C56	0.1 (3)
N3—C4—C41—C46	−31.5 (2)	C53—C54—C55—C58	−179.87 (19)
C5—C4—C41—C46	151.79 (18)	C54—C55—C56—C57	0.6 (3)
C46—C41—C42—C43	−0.3 (3)	C58—C55—C56—C57	−179.47 (19)
C4—C41—C42—C43	−177.57 (17)	C55—C56—C57—C52	−0.9 (3)
C41—C42—C43—C44	−0.8 (3)	C53—C52—C57—C56	0.5 (3)
C42—C43—C44—C45	1.4 (3)	C51—C52—C57—C56	177.33 (17)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C47—H47B···O5ⁱ	0.96	2.47	3.393 (3)	162

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

Experimental details

Crystal data
Chemical formula	C₂₀H₁₈N₂OS
M_r	334.42
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	5.8203 (5), 15.6178 (10), 19.4161 (16)
β (°)	104.466 (6)
V (Å³)	1709.0 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.20
Crystal size (mm)	0.61 × 0.35 × 0.20

Data collection
Diffractometer	Stoe IPDSII diffractometer
Absorption correction	Integration (X-RED32; Stoe & Cie, 2002)
T_min, T_max	0.923, 0.978
No. of measured, independent and observed [I > 2σ(I)] reflections	14819, 3294, 2225
R_int	0.043
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.039, 0.107, 1.01
No. of reflections	3294
No. of parameters	220
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.17, −0.27

Computer programs: X-AREA (Stoe & Cie, 2002), X-RED32 (Stoe & Cie, 2002), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999) and PLATON (Spek, 2003).