7-Amino-1,3-dimethyl-5-(4-nitro­phen­yl)-2,4-dioxo-1,2,3,4-tetra­hydro­pyrido[2,3-d]pyrimidine-6-carbonitrile

Zhou, J.-X.; Niu, L.-H.; Li, X.-Y.; Shi, D.-Q.

doi:10.1107/S1600536807019356

7-Amino-1,3-dimethyl-5-(4-nitrophenyl)-2,4-dioxo-1,2,3,4-tetrahydropyrido[2,3-d]pyrimidine-6-carbonitrile

J.-X. Zhou, L.-H. Niu, X.-Y. Li and D.-Q. Shi

The title compound, C₁₆H₁₂N₆O₄, was synthesized by the reaction of 6-amino-1,3-dimethylpyrimidine-2,4(1H,3H)-dione and 4-nitrobenzaldehyde with malononitrile in water in the presence of triethylbenzylammonium chloride at 363 K. X-ray analysis reveals that the pyrimidine ring adopts a flattened envelope conformation. The dihedral angle between the pyridine and benzene rings is 81.83 (3)°. Molecules are linked by N—H

O, C—H

O and C—H

N hydrogen bonds, forming a three-dimensional network.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807019356/ci2368sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807019356/ci2368Isup2.hkl Contains datablock I

CCDC reference: 647687

checkCIF report

Key indicators

Single-crystal X-ray study
T = 193 K
Mean (C-C) = 0.002 Å
R factor = 0.046
wR factor = 0.122
Data-to-parameter ratio = 14.6

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT230_ALERT_2_C Hirshfeld Test Diff for    O3     -   N6      ..       5.14 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C4     -   C14     ..       5.33 su
PLAT371_ALERT_2_C Long   C(sp2)-C(sp1) Bond  C4     -   C14    ...       1.43 Ang.
PLAT432_ALERT_2_C Short Inter X...Y Contact  N4     ..  C6      ..       2.99 Ang.

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   5 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
   4 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
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Comment top

The importance of uracil and its annelated derivatives is well recognized in synthetic (Sasaki et al., 1980; Bhuyan et al., 1999) as well as biological (Griengl et al., 1987; Pontikis et al., 1994) chemistry. With the development of clinically useful anticancer and antiviral drugs (Clercq et al., 1986; Jones et al., 1979), there has recently been remarkable interest in the synthetic manipulations of uracils (Hirota et al., 1981). Pyrido[2,3-d]pyrimidines represent a heterocyclic ring system of considerable interest because of several biological activities associated with this scaffold. Some analogues have been found to act as anticancer agents inhibiting dihydrofolate reductases or tyrosine kinases (Gangjee et al., 1999), while others are known antiviral agents (Nasr et al., 2002). We report here the crystal structure of the title compound, (I).

The pyrimidine ring adopts a flattened envelope conformation, with atom C6 deviating from the C1/C2/C7/N2/N3 plane by 0.144 (2) Å (Fig. 1). The dihedral angle between the C1—C5/N1 and C1/C2/C7/N2/N3 planes is 0.56 (7)°. The dihedral angle between the pyridine and benzene rings is 81.83 (3)°. The nitro group is coplanar with the attached benzene ring.

In the crystal structure, the molecules are linked to form a three-dimensional network (Fig. 2) by N—H···O, C—H···O and C—H···N type hydrogen bonds (Table 1).

Related literature top

For general background, see: Bhuyan et al. (1999); Clercq (1986); Gangjee et al. (1999); Griengl et al. (1987); Hirota et al. (1981); Jones et al. (1979); Nasr & Gineinah (2002); Pontikis & Monneret (1994); Sasaki et al. (1980).

Experimental top

Compound (I) was prepared by the reaction of 6-amino-1,3-dimethylpyrimidine-2,4(1H,3H)-dione (2 mmol) and 4-nitrobenzaldehyde (2 mmol) with malononitrile (2 mmol) in water (10 ml) in the presence of triethylbenzylammonium chloride (0.15 g) at 363 K. Crystals of (I) suitable for X-ray diffraction were obtained by slow evaporation of an ethanol solution.

Structure description top

In the crystal structure, the molecules are linked to form a three-dimensional network (Fig. 2) by N—H···O, C—H···O and C—H···N type hydrogen bonds (Table 1).

Computing details top

Data collection: CrystalClear (Rigaku, 2000); cell refinement: CrystalClear; data reduction: CrystalStructure (Rigaku/MSC, 2003); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1999); software used to prepare material for publication: SHELXL97.

Figures top

	Fig. 1. The molecular structure of (I), showing 40% probability displacement ellipsoids and the atom-numbering scheme.
	Fig. 2. The crystal packing of (I). Hydrogen bonds are shown as dashed lines.

7-Amino-1,3-dimethyl-5-(4-nitrophenyl)-2,4-dioxo-1,2,3,4- tetrahydropyrido[2,3-d]pyrimidine-6-carbonitrile top

Crystal data top

C₁₆H₁₂N₆O₄	F(000) = 728
M_r = 352.32	D_x = 1.493 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71070 Å
Hall symbol: -P 2yn	Cell parameters from 6117 reflections
a = 9.6209 (9) Å	θ = 3.1–27.5°
b = 11.7064 (12) Å	µ = 0.11 mm⁻¹
c = 14.5493 (16) Å	T = 193 K
β = 106.939 (3)°	Block, gold
V = 1567.5 (3) Å³	0.60 × 0.40 × 0.32 mm
Z = 4

Data collection top

Rigaku Mercury diffractometer	3595 independent reflections
Radiation source: fine-focus sealed tube	3259 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.021
Detector resolution: 7.31 pixels mm^-1	θ_max = 27.5°, θ_min = 3.4°
ω scans	h = −12→10
Absorption correction: multi-scan (Jacobson, 1998)	k = −15→14
T_min = 0.936, T_max = 0.965	l = −18→18
17123 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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.122	H atoms treated by a mixture of independent and constrained refinement
S = 1.11	w = 1/[σ²(F_o²) + (0.0637P)² + 0.3577P] where P = (F_o² + 2F_c²)/3
3595 reflections	(Δ/σ)_max = 0.001
246 parameters	Δρ_max = 0.24 e Å⁻³
0 restraints	Δρ_min = −0.25 e Å⁻³

Crystal data top

C₁₆H₁₂N₆O₄	V = 1567.5 (3) Å³
M_r = 352.32	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 9.6209 (9) Å	µ = 0.11 mm⁻¹
b = 11.7064 (12) Å	T = 193 K
c = 14.5493 (16) Å	0.60 × 0.40 × 0.32 mm
β = 106.939 (3)°

Data collection top

Rigaku Mercury diffractometer	3595 independent reflections
Absorption correction: multi-scan (Jacobson, 1998)	3259 reflections with I > 2σ(I)
T_min = 0.936, T_max = 0.965	R_int = 0.021
17123 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.046	0 restraints
wR(F²) = 0.122	H atoms treated by a mixture of independent and constrained refinement
S = 1.11	Δρ_max = 0.24 e Å⁻³
3595 reflections	Δρ_min = −0.25 e Å⁻³
246 parameters

Special details top

Experimental. ¹H NMR (DMSO-d₆, δ): 3.08 (3H, s, CH₃), 3.51 (3H, s, CH₃), 7.57 (2H, d, J = 8.8 Hz, ArH), 8.02 (2H, s, NH₂), 8.32 (2H, d, J = 8.8 Hz, ArH).

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
O1	0.40040 (11)	0.58289 (9)	0.61943 (7)	0.0371 (3)
O2	0.27711 (11)	0.53458 (9)	0.89364 (8)	0.0408 (3)
O3	0.40782 (12)	0.88345 (11)	0.25427 (7)	0.0449 (3)
O4	0.58170 (12)	0.76386 (10)	0.26221 (7)	0.0434 (3)
N1	0.62792 (11)	0.80081 (9)	0.90036 (7)	0.0271 (2)
N2	0.32494 (12)	0.57102 (9)	0.75276 (8)	0.0297 (3)
N3	0.45263 (12)	0.66590 (10)	0.89615 (7)	0.0293 (3)
N4	0.86032 (13)	0.96383 (11)	0.68190 (8)	0.0362 (3)
N5	0.81041 (13)	0.93043 (10)	0.91201 (8)	0.0324 (3)
N6	0.50203 (12)	0.81687 (10)	0.29905 (8)	0.0314 (3)
C1	0.53176 (13)	0.72749 (11)	0.84755 (9)	0.0254 (3)
C2	0.50682 (13)	0.70913 (11)	0.74838 (9)	0.0250 (3)
C3	0.58756 (13)	0.77512 (10)	0.70202 (8)	0.0232 (3)
C4	0.69181 (13)	0.84923 (10)	0.75676 (8)	0.0252 (3)
C5	0.71081 (13)	0.85990 (11)	0.85729 (8)	0.0255 (3)
C6	0.40912 (14)	0.61853 (11)	0.70021 (9)	0.0273 (3)
C7	0.34766 (14)	0.58771 (12)	0.85086 (10)	0.0306 (3)
C8	0.56079 (13)	0.77645 (10)	0.59552 (8)	0.0233 (3)
C9	0.44885 (14)	0.84520 (11)	0.54105 (9)	0.0276 (3)
H9	0.3861	0.8832	0.5708	0.033*
C10	0.42892 (14)	0.85827 (11)	0.44323 (9)	0.0279 (3)
H10	0.3536	0.9057	0.4055	0.033*
C11	0.52071 (14)	0.80098 (11)	0.40213 (8)	0.0260 (3)
C12	0.63132 (14)	0.73093 (11)	0.45431 (9)	0.0291 (3)
H12	0.6916	0.6912	0.4236	0.035*
C13	0.65246 (14)	0.71979 (11)	0.55214 (9)	0.0277 (3)
H13	0.7293	0.6736	0.5896	0.033*
C14	0.78334 (13)	0.91355 (11)	0.71367 (9)	0.0267 (3)
C15	0.21570 (17)	0.48538 (13)	0.70592 (12)	0.0409 (4)
H15A	0.1877	0.4965	0.6362	0.061*
H15B	0.1299	0.4938	0.7288	0.061*
H15C	0.2565	0.4087	0.7216	0.061*
C16	0.48811 (17)	0.67789 (15)	1.00141 (10)	0.0394 (3)
H16A	0.4223	0.6301	1.0251	0.059*
H16B	0.4769	0.7579	1.0177	0.059*
H16C	0.5887	0.6537	1.0313	0.059*
H5A	0.8264 (18)	0.9259 (15)	0.9718 (13)	0.038 (4)*
H5B	0.877 (2)	0.9721 (17)	0.8866 (14)	0.056 (5)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0469 (6)	0.0400 (6)	0.0246 (5)	−0.0109 (4)	0.0107 (4)	−0.0044 (4)
O2	0.0414 (6)	0.0428 (6)	0.0466 (6)	−0.0009 (5)	0.0259 (5)	0.0087 (5)
O3	0.0447 (6)	0.0592 (7)	0.0266 (5)	0.0033 (5)	0.0037 (4)	0.0130 (5)
O4	0.0593 (7)	0.0475 (6)	0.0273 (5)	−0.0024 (5)	0.0185 (5)	−0.0043 (4)
N1	0.0302 (6)	0.0302 (6)	0.0209 (5)	0.0041 (4)	0.0072 (4)	0.0007 (4)
N2	0.0285 (6)	0.0288 (6)	0.0345 (6)	−0.0009 (4)	0.0135 (5)	−0.0006 (4)
N3	0.0314 (6)	0.0353 (6)	0.0244 (5)	0.0033 (4)	0.0132 (4)	0.0039 (4)
N4	0.0368 (6)	0.0375 (7)	0.0351 (6)	−0.0069 (5)	0.0116 (5)	−0.0008 (5)
N5	0.0383 (6)	0.0349 (6)	0.0211 (5)	−0.0030 (5)	0.0040 (5)	−0.0015 (5)
N6	0.0360 (6)	0.0352 (6)	0.0225 (5)	−0.0102 (5)	0.0077 (4)	0.0001 (4)
C1	0.0266 (6)	0.0273 (6)	0.0241 (6)	0.0063 (5)	0.0100 (5)	0.0037 (5)
C2	0.0271 (6)	0.0254 (6)	0.0231 (6)	0.0026 (5)	0.0084 (5)	0.0017 (5)
C3	0.0251 (6)	0.0236 (6)	0.0208 (5)	0.0047 (4)	0.0064 (4)	0.0017 (4)
C4	0.0283 (6)	0.0249 (6)	0.0224 (6)	0.0027 (5)	0.0072 (5)	0.0015 (5)
C5	0.0274 (6)	0.0254 (6)	0.0226 (6)	0.0062 (5)	0.0054 (5)	0.0012 (4)
C6	0.0272 (6)	0.0284 (6)	0.0264 (6)	0.0019 (5)	0.0079 (5)	0.0035 (5)
C7	0.0288 (7)	0.0318 (7)	0.0358 (7)	0.0060 (5)	0.0164 (5)	0.0048 (5)
C8	0.0262 (6)	0.0229 (6)	0.0205 (6)	−0.0030 (4)	0.0065 (4)	0.0009 (4)
C9	0.0287 (6)	0.0297 (6)	0.0252 (6)	0.0025 (5)	0.0091 (5)	0.0011 (5)
C10	0.0274 (6)	0.0291 (6)	0.0249 (6)	0.0010 (5)	0.0041 (5)	0.0046 (5)
C11	0.0294 (6)	0.0286 (6)	0.0194 (5)	−0.0078 (5)	0.0060 (5)	0.0007 (5)
C12	0.0320 (7)	0.0317 (7)	0.0256 (6)	0.0011 (5)	0.0116 (5)	−0.0016 (5)
C13	0.0297 (6)	0.0282 (6)	0.0248 (6)	0.0041 (5)	0.0074 (5)	0.0025 (5)
C14	0.0281 (6)	0.0264 (6)	0.0234 (6)	0.0009 (5)	0.0042 (5)	−0.0015 (5)
C15	0.0391 (8)	0.0370 (8)	0.0514 (9)	−0.0099 (6)	0.0205 (7)	−0.0088 (6)
C16	0.0392 (8)	0.0573 (9)	0.0248 (6)	0.0031 (7)	0.0139 (6)	0.0078 (6)

Geometric parameters (Å, º) top

O1—C6	1.2267 (16)	C3—C4	1.3883 (17)
O2—C7	1.2169 (16)	C3—C8	1.4950 (16)
O3—N6	1.2285 (16)	C4—C5	1.4257 (16)
O4—N6	1.2245 (15)	C4—C14	1.4343 (17)
N1—C1	1.3300 (17)	C8—C9	1.3922 (17)
N1—C5	1.3411 (17)	C8—C13	1.3930 (17)
N2—C6	1.3823 (16)	C9—C10	1.3881 (17)
N2—C7	1.3933 (17)	C9—H9	0.95
N2—C15	1.4686 (18)	C10—C11	1.3766 (18)
N3—C7	1.3799 (18)	C10—H10	0.95
N3—C1	1.3830 (16)	C11—C12	1.3822 (18)
N3—C16	1.4755 (17)	C12—C13	1.3841 (17)
N4—C14	1.1437 (17)	C12—H12	0.95
N5—C5	1.3376 (17)	C13—H13	0.95
N5—H5A	0.84 (2)	C15—H15A	0.98
N5—H5B	0.96 (2)	C15—H15B	0.98
N6—C11	1.4694 (15)	C15—H15C	0.98
C1—C2	1.4085 (17)	C16—H16A	0.98
C2—C3	1.4001 (17)	C16—H16B	0.98
C2—C6	1.4546 (18)	C16—H16C	0.98

C1—N1—C5	118.12 (10)	N3—C7—N2	117.17 (11)
C6—N2—C7	124.61 (11)	C9—C8—C13	120.28 (11)
C6—N2—C15	118.25 (11)	C9—C8—C3	117.85 (11)
C7—N2—C15	116.65 (11)	C13—C8—C3	121.60 (11)
C7—N3—C1	122.48 (11)	C10—C9—C8	120.02 (12)
C7—N3—C16	118.33 (11)	C10—C9—H9	120.0
C1—N3—C16	119.06 (11)	C8—C9—H9	120.0
C5—N5—H5A	117.4 (12)	C11—C10—C9	118.50 (11)
C5—N5—H5B	121.8 (12)	C11—C10—H10	120.7
H5A—N5—H5B	119.3 (17)	C9—C10—H10	120.7
O4—N6—O3	123.27 (11)	C10—C11—C12	122.63 (11)
O4—N6—C11	118.46 (11)	C10—C11—N6	118.58 (11)
O3—N6—C11	118.27 (11)	C12—C11—N6	118.78 (11)
N1—C1—N3	115.79 (11)	C11—C12—C13	118.66 (11)
N1—C1—C2	124.92 (11)	C11—C12—H12	120.7
N3—C1—C2	119.30 (12)	C13—C12—H12	120.7
C3—C2—C1	117.16 (11)	C12—C13—C8	119.89 (11)
C3—C2—C6	122.79 (11)	C12—C13—H13	120.1
C1—C2—C6	119.88 (11)	C8—C13—H13	120.1
C4—C3—C2	118.55 (11)	N4—C14—C4	177.66 (14)
C4—C3—C8	117.74 (10)	N2—C15—H15A	109.5
C2—C3—C8	123.56 (11)	N2—C15—H15B	109.5
C3—C4—C5	119.90 (11)	H15A—C15—H15B	109.5
C3—C4—C14	120.69 (11)	N2—C15—H15C	109.5
C5—C4—C14	119.40 (11)	H15A—C15—H15C	109.5
N5—C5—N1	117.43 (11)	H15B—C15—H15C	109.5
N5—C5—C4	121.35 (12)	N3—C16—H16A	109.5
N1—C5—C4	121.21 (11)	N3—C16—H16B	109.5
O1—C6—N2	120.37 (12)	H16A—C16—H16B	109.5
O1—C6—C2	124.32 (11)	N3—C16—H16C	109.5
N2—C6—C2	115.30 (11)	H16A—C16—H16C	109.5
O2—C7—N3	122.31 (13)	H16B—C16—H16C	109.5
O2—C7—N2	120.52 (13)

C5—N1—C1—N3	177.84 (10)	C1—C2—C6—O1	−166.42 (12)
C5—N1—C1—C2	−1.95 (18)	C3—C2—C6—N2	−172.61 (11)
C7—N3—C1—N1	179.16 (11)	C1—C2—C6—N2	12.36 (17)
C16—N3—C1—N1	−5.18 (17)	C1—N3—C7—O2	−179.17 (12)
C7—N3—C1—C2	−1.03 (18)	C16—N3—C7—O2	5.15 (19)
C16—N3—C1—C2	174.63 (11)	C1—N3—C7—N2	1.01 (18)
N1—C1—C2—C3	−1.43 (18)	C16—N3—C7—N2	−174.68 (11)
N3—C1—C2—C3	178.78 (10)	C6—N2—C7—O2	−173.21 (12)
N1—C1—C2—C6	173.87 (11)	C15—N2—C7—O2	−1.41 (19)
N3—C1—C2—C6	−5.92 (18)	C6—N2—C7—N3	6.62 (19)
C1—C2—C3—C4	3.48 (17)	C15—N2—C7—N3	178.41 (11)
C6—C2—C3—C4	−171.68 (11)	C4—C3—C8—C9	−94.22 (14)
C1—C2—C3—C8	−172.06 (11)	C2—C3—C8—C9	81.35 (15)
C6—C2—C3—C8	12.79 (18)	C4—C3—C8—C13	79.81 (15)
C2—C3—C4—C5	−2.33 (17)	C2—C3—C8—C13	−104.62 (15)
C8—C3—C4—C5	173.46 (10)	C13—C8—C9—C10	−0.53 (19)
C2—C3—C4—C14	176.22 (11)	C3—C8—C9—C10	173.59 (11)
C8—C3—C4—C14	−7.98 (17)	C8—C9—C10—C11	0.76 (19)
C1—N1—C5—N5	−177.77 (11)	C9—C10—C11—C12	0.19 (19)
C1—N1—C5—C4	3.20 (17)	C9—C10—C11—N6	−178.55 (11)
C3—C4—C5—N5	179.91 (11)	O4—N6—C11—C10	−178.40 (11)
C14—C4—C5—N5	1.34 (18)	O3—N6—C11—C10	2.14 (17)
C3—C4—C5—N1	−1.10 (18)	O4—N6—C11—C12	2.81 (18)
C14—C4—C5—N1	−179.67 (11)	O3—N6—C11—C12	−176.64 (12)
C7—N2—C6—O1	165.81 (12)	C10—C11—C12—C13	−1.3 (2)
C15—N2—C6—O1	−5.87 (19)	N6—C11—C12—C13	177.39 (11)
C7—N2—C6—C2	−13.03 (18)	C11—C12—C13—C8	1.55 (19)
C15—N2—C6—C2	175.30 (11)	C9—C8—C13—C12	−0.64 (19)
C3—C2—C6—O1	8.6 (2)	C3—C8—C13—C12	−174.53 (11)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N5—H5A···O1ⁱ	0.84 (2)	2.06 (2)	2.8912 (15)	171 (2)
N5—H5B···O1ⁱⁱ	0.96 (2)	2.53 (2)	3.4463 (17)	160 (2)
C9—H9···O2ⁱⁱⁱ	0.95	2.52	3.4275 (16)	160
C10—H10···N4^iv	0.95	2.58	3.5275 (18)	174
C13—H13···O3ⁱ	0.95	2.60	3.4547 (17)	151
C15—H15C···O4^v	0.98	2.52	3.464 (2)	162

Symmetry codes: (i) x+1/2, −y+3/2, z+1/2; (ii) −x+3/2, y+1/2, −z+3/2; (iii) −x+1/2, y+1/2, −z+3/2; (iv) −x+1, −y+2, −z+1; (v) −x+1, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₆H₁₂N₆O₄
M_r	352.32
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	193
a, b, c (Å)	9.6209 (9), 11.7064 (12), 14.5493 (16)
β (°)	106.939 (3)
V (Å³)	1567.5 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.11
Crystal size (mm)	0.60 × 0.40 × 0.32

Data collection
Diffractometer	Rigaku Mercury
Absorption correction	Multi-scan (Jacobson, 1998)
T_min, T_max	0.936, 0.965
No. of measured, independent and observed [I > 2σ(I)] reflections	17123, 3595, 3259
R_int	0.021
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.046, 0.122, 1.11
No. of reflections	3595
No. of parameters	246
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.24, −0.25

Computer programs: CrystalClear (Rigaku, 2000), CrystalClear, CrystalStructure (Rigaku/MSC, 2003), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1999), SHELXL97.