Ethyl 7-chloro­methyl-5-(2-chloro­phen­yl)-7-hydr­oxy-2-methyl­sulfanyl-4,5,6,7-tetra­hydro-1,2,4-triazolo[1,5-a]pyrimidine-6-carboxyl­ate

Huang, S.

doi:10.1107/S1600536809039373

Ethyl 7-chloromethyl-5-(2-chlorophenyl)-7-hydroxy-2-methylsulfanyl-4,5,6,7-tetrahydro-1,2,4-triazolo[1,5-a]pyrimidine-6-carboxylate

In the title compound, C₁₆H₁₈Cl₂N₄O₃S, the five-membered ring is almost planar [maximum deviation = 0.011 (3) Å] and the six-membered ring adopts an envelope conformation. In the crystal structure, N—H

N, O—H

N and C—H

O interactions link molecules into a three-dimensional network.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536809039373/hb5113sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536809039373/hb5113Isup2.hkl Contains datablock I

CCDC reference: 754267

checkCIF report

Key indicators

Single-crystal X-ray study
T = 292 K
Mean (C-C) = 0.004 Å
R factor = 0.053
wR factor = 0.141
Data-to-parameter ratio = 15.1

checkCIF/PLATON results

No syntax errors found



Alert level G
PLAT154_ALERT_1_G The su's on the Cell Angles are Equal  (x 10000)        300 Deg.
PLAT793_ALERT_4_G The Model has Chirality at C7      (Verify) ....          R
PLAT793_ALERT_4_G The Model has Chirality at C8      (Verify) ....          R
PLAT793_ALERT_4_G The Model has Chirality at C12     (Verify) ....          R

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

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 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
   3 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Comment top

In recent years, tetrahydro triazolo1,5-a]pyrimidine derivatives nave attracted interest as potential biologically active compounds (Pryadeina et al., 2004). In this paper, we present the structure of one such analogue, the title compound, (I) (Fig. 1), in which the bond lengths (Allen et al., 1987) and angles are within normal ranges.

The bicyclic triazolopyrimidine system is not on the same plane because they can not form a conjugated system. Ring A (N2-4/C14-15) is close to planarity with a maximum deviation of 0.011Å for C15. Rng B (N1-2/C7-8/C12/C14) dopt envelope conformations with atom C8 displaced by 0.333 (3) Å from the plane of the other ring atoms. The dihedral angle between the Ring (C1-C6) and the ring A is 51.86°.

In the crystal structure, weak N-H···N, O-H···N and C-H···O interactions link the molecules into a three-dimensional network (Fig. 2).

Related literature top

For general background to tetrahydro triazolo[1,5-a]pyrimidine derivatives as potential biologically active compounds, see: Pryadeina et al. (2004). For related structures, see: Chen et al. (2005); Hu et al. (2005). For bond-length data, see: Allen et al. (1987).

Experimental top

A solution of 4-chloro acetylacetic ester (1 mmol), 2-chloro benzaldehyde (1 mmol), and 3-amino-5-methylthio-1,2,4-triazole (1mmol) in water (3 ml) containing a catalytic amount of TSA was heated under 353 K for 10 h. The resulting mixture was extracted with CH₂Cl₂ and the extra was dried over sodium sulfate, filtered, the filtrate was condensed under reduced pressure and the residue was purified by chromatography on SiO₂ to afford the title compound. Colourless blocks of (I) were grown from an acetone solution at 293K. ¹H NMR (CDCl₃, 400 MHz): σ 7.03-7.40(m, 4 H), 6.42(s, 1H), 4.99(d, 1H), 4.35(d, 1H), 4.00(q,2 H), 3.91(d, 1H), 3.05(d, 1H), 2.35(s, 3H), 1.03(t,3H).

Structure description top

In the crystal structure, weak N-H···N, O-H···N and C-H···O interactions link the molecules into a three-dimensional network (Fig. 2).

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of (I) with displacement ellipsoids drawn at the 50% probability level.
	Fig. 2. A partial packing diagram of (I). Hydrogen bonds are shown as dashed lines. H atoms not involved in hydrogen bonding have been omitted for clarity.

Ethyl 7-chloromethyl-5-(2-chlorophenyl)-7-hydroxy-2-methylsulfanyl-4,5,6,7-tetrahydro-1,2,4-triazolo[1,5-a]pyrimidine-6-carboxylate top

Crystal data top

C₁₆H₁₈Cl₂N₄O₃S	Z = 2
M_r = 417.30	F(000) = 432
Triclinic, P1	D_x = 1.430 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.4534 (14) Å	Cell parameters from 2018 reflections
b = 10.5082 (17) Å	θ = 2.5–24.1°
c = 12.0846 (19) Å	µ = 0.47 mm⁻¹
α = 66.660 (3)°	T = 292 K
β = 79.519 (3)°	Block, colourless
γ = 84.795 (3)°	0.30 × 0.20 × 0.10 mm
V = 969.0 (3) Å³

Data collection top

Bruker SMART 4K CCD diffractometer	2661 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.025
Graphite monochromator	θ_max = 26.0°, θ_min = 1.9°
φ and ω scans	h = −10→10
6772 measured reflections	k = −12→12
3759 independent reflections	l = −14→14

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)] = 0.053	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.141	H atoms treated by a mixture of independent and constrained refinement
S = 1.08	w = 1/[σ²(F_o²) + (0.07P)²] where P = (F_o² + 2F_c²)/3
3759 reflections	(Δ/σ)_max = 0.001
249 parameters	Δρ_max = 0.43 e Å⁻³
0 restraints	Δρ_min = −0.33 e Å⁻³

Crystal data top

C₁₆H₁₈Cl₂N₄O₃S	γ = 84.795 (3)°
M_r = 417.30	V = 969.0 (3) Å³
Triclinic, P1	Z = 2
a = 8.4534 (14) Å	Mo Kα radiation
b = 10.5082 (17) Å	µ = 0.47 mm⁻¹
c = 12.0846 (19) Å	T = 292 K
α = 66.660 (3)°	0.30 × 0.20 × 0.10 mm
β = 79.519 (3)°

Data collection top

Bruker SMART 4K CCD diffractometer	2661 reflections with I > 2σ(I)
6772 measured reflections	R_int = 0.025
3759 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.053	0 restraints
wR(F²) = 0.141	H atoms treated by a mixture of independent and constrained refinement
S = 1.08	Δρ_max = 0.43 e Å⁻³
3759 reflections	Δρ_min = −0.33 e Å⁻³
249 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
Cl1	0.68839 (13)	0.60065 (10)	0.98954 (7)	0.0933 (4)
Cl2	0.60921 (11)	0.36582 (8)	0.66235 (7)	0.0709 (3)
S1	1.08176 (11)	0.90864 (8)	0.17205 (6)	0.0681 (3)
C1	0.6041 (4)	0.7582 (3)	0.9073 (2)	0.0571 (8)
C2	0.4887 (4)	0.8210 (4)	0.9701 (3)	0.0747 (10)
H2	0.4601	0.7782	1.0543	0.090*
C3	0.4181 (4)	0.9457 (4)	0.9068 (3)	0.0775 (11)
H3	0.3413	0.9870	0.9483	0.093*
C4	0.4602 (4)	1.0087 (3)	0.7840 (3)	0.0684 (9)
H4	0.4126	1.0933	0.7415	0.082*
C5	0.5738 (3)	0.9472 (3)	0.7221 (2)	0.0510 (7)
H5	0.6018	0.9919	0.6380	0.061*
C6	0.6471 (3)	0.8217 (3)	0.7812 (2)	0.0414 (6)
C7	0.7640 (3)	0.7517 (2)	0.7107 (2)	0.0382 (6)
H7	0.835 (3)	0.694 (3)	0.758 (2)	0.046*
C8	0.6777 (3)	0.6492 (2)	0.6789 (2)	0.0351 (5)
H8	0.645 (3)	0.574 (2)	0.755 (2)	0.042*
C9	0.5292 (3)	0.7157 (3)	0.6256 (2)	0.0441 (6)
C10	0.2503 (4)	0.7571 (4)	0.6852 (3)	0.0809 (11)
H10A	0.1955	0.7190	0.6417	0.097*
H10B	0.2709	0.8541	0.6349	0.097*
C11	0.1517 (4)	0.7428 (4)	0.8024 (3)	0.0821 (11)
H11A	0.1188	0.6484	0.8461	0.123*
H11B	0.0582	0.8025	0.7881	0.123*
H11C	0.2133	0.7680	0.8496	0.123*
C12	0.7963 (3)	0.5897 (2)	0.5979 (2)	0.0369 (6)
C13	0.7175 (3)	0.5062 (3)	0.5449 (2)	0.0461 (6)
H13A	0.7998	0.4709	0.4964	0.055*
H13B	0.6449	0.5662	0.4916	0.055*
C14	0.8996 (3)	0.8292 (2)	0.5003 (2)	0.0395 (6)
C15	0.9936 (3)	0.8369 (3)	0.3248 (2)	0.0441 (6)
C16	1.0255 (5)	0.7895 (3)	0.1151 (3)	0.0830 (11)
H16A	1.0832	0.7033	0.1477	0.125*
H16B	1.0510	0.8271	0.0276	0.125*
H16C	0.9119	0.7740	0.1392	0.125*
N1	0.8465 (3)	0.8568 (2)	0.59986 (19)	0.0461 (6)
H1	0.894 (3)	0.929 (3)	0.608 (2)	0.055*
N2	0.8708 (3)	0.7083 (2)	0.49519 (17)	0.0410 (5)
N3	0.9342 (3)	0.7110 (2)	0.37947 (17)	0.0417 (5)
N4	0.9794 (3)	0.9135 (2)	0.39433 (17)	0.0441 (5)
O1	0.5267 (3)	0.7939 (2)	0.52207 (17)	0.0682 (6)
O2	0.4005 (2)	0.6814 (2)	0.71234 (18)	0.0611 (6)
O3	0.9120 (2)	0.51348 (18)	0.66938 (16)	0.0448 (5)
H3A	0.953 (4)	0.458 (3)	0.647 (3)	0.067*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.1212 (8)	0.0852 (7)	0.0451 (5)	−0.0024 (6)	−0.0173 (5)	0.0064 (4)
Cl2	0.0932 (6)	0.0500 (5)	0.0662 (5)	−0.0327 (4)	−0.0159 (4)	−0.0111 (4)
S1	0.1055 (7)	0.0475 (5)	0.0361 (4)	−0.0024 (4)	0.0124 (4)	−0.0101 (3)
C1	0.073 (2)	0.0615 (19)	0.0356 (14)	−0.0172 (16)	0.0008 (14)	−0.0183 (13)
C2	0.084 (2)	0.101 (3)	0.0403 (16)	−0.028 (2)	0.0177 (16)	−0.0353 (18)
C3	0.078 (2)	0.087 (3)	0.081 (2)	−0.019 (2)	0.020 (2)	−0.056 (2)
C4	0.068 (2)	0.0568 (19)	0.084 (2)	−0.0057 (16)	0.0090 (18)	−0.0391 (17)
C5	0.0643 (18)	0.0407 (16)	0.0465 (15)	−0.0049 (14)	0.0028 (13)	−0.0194 (12)
C6	0.0477 (15)	0.0436 (15)	0.0343 (13)	−0.0110 (12)	0.0024 (11)	−0.0184 (11)
C7	0.0433 (15)	0.0344 (13)	0.0332 (12)	−0.0019 (11)	−0.0027 (11)	−0.0104 (10)
C8	0.0390 (14)	0.0291 (12)	0.0315 (12)	−0.0017 (10)	−0.0041 (10)	−0.0063 (10)
C9	0.0513 (16)	0.0398 (15)	0.0434 (15)	0.0048 (12)	−0.0119 (13)	−0.0179 (12)
C10	0.052 (2)	0.107 (3)	0.089 (3)	0.030 (2)	−0.0287 (18)	−0.043 (2)
C11	0.051 (2)	0.096 (3)	0.109 (3)	0.0175 (19)	−0.021 (2)	−0.051 (2)
C12	0.0450 (14)	0.0256 (12)	0.0385 (13)	−0.0016 (10)	−0.0073 (11)	−0.0102 (10)
C13	0.0582 (17)	0.0355 (14)	0.0434 (14)	−0.0058 (12)	−0.0109 (12)	−0.0117 (11)
C14	0.0477 (15)	0.0316 (13)	0.0369 (13)	−0.0033 (11)	0.0007 (11)	−0.0136 (10)
C15	0.0556 (16)	0.0331 (14)	0.0355 (13)	0.0054 (12)	0.0031 (11)	−0.0107 (11)
C16	0.141 (3)	0.067 (2)	0.0378 (16)	0.008 (2)	−0.0113 (18)	−0.0201 (15)
N1	0.0583 (14)	0.0386 (12)	0.0421 (12)	−0.0177 (11)	0.0107 (10)	−0.0208 (10)
N2	0.0537 (13)	0.0327 (11)	0.0351 (11)	−0.0054 (10)	0.0035 (9)	−0.0150 (8)
N3	0.0580 (14)	0.0316 (11)	0.0339 (11)	0.0016 (10)	−0.0019 (9)	−0.0138 (9)
N4	0.0567 (14)	0.0328 (11)	0.0374 (11)	−0.0029 (10)	0.0074 (10)	−0.0137 (9)
O1	0.0783 (15)	0.0711 (14)	0.0463 (12)	0.0242 (12)	−0.0219 (10)	−0.0138 (10)
O2	0.0390 (11)	0.0711 (14)	0.0615 (12)	0.0076 (10)	−0.0113 (9)	−0.0140 (10)
O3	0.0513 (11)	0.0359 (10)	0.0513 (11)	0.0109 (8)	−0.0149 (9)	−0.0207 (8)

Geometric parameters (Å, º) top

Cl1—C1	1.725 (3)	C10—O2	1.454 (3)
Cl2—C13	1.773 (2)	C10—C11	1.465 (5)
S1—C15	1.740 (2)	C10—H10A	0.9700
S1—C16	1.783 (4)	C10—H10B	0.9700
C1—C6	1.392 (3)	C11—H11A	0.9600
C1—C2	1.404 (4)	C11—H11B	0.9600
C2—C3	1.374 (5)	C11—H11C	0.9600
C2—H2	0.9300	C12—O3	1.401 (3)
C3—C4	1.356 (4)	C12—N2	1.456 (3)
C3—H3	0.9300	C12—C13	1.526 (3)
C4—C5	1.381 (4)	C13—H13A	0.9700
C4—H4	0.9300	C13—H13B	0.9700
C5—C6	1.378 (4)	C14—N4	1.332 (3)
C5—H5	0.9300	C14—N1	1.337 (3)
C6—C7	1.517 (4)	C14—N2	1.342 (3)
C7—N1	1.458 (3)	C15—N3	1.321 (3)
C7—C8	1.554 (3)	C15—N4	1.360 (3)
C7—H7	0.92 (3)	C16—H16A	0.9600
C8—C9	1.502 (3)	C16—H16B	0.9600
C8—C12	1.539 (3)	C16—H16C	0.9600
C8—H8	0.96 (2)	N1—H1	0.93 (3)
C9—O1	1.198 (3)	N2—N3	1.393 (3)
C9—O2	1.329 (3)	O3—H3A	0.77 (3)

C15—S1—C16	101.76 (14)	C10—C11—H11A	109.5
C6—C1—C2	120.3 (3)	C10—C11—H11B	109.5
C6—C1—Cl1	121.1 (2)	H11A—C11—H11B	109.5
C2—C1—Cl1	118.6 (2)	C10—C11—H11C	109.5
C3—C2—C1	119.9 (3)	H11A—C11—H11C	109.5
C3—C2—H2	120.0	H11B—C11—H11C	109.5
C1—C2—H2	120.0	O3—C12—N2	109.8 (2)
C4—C3—C2	120.2 (3)	O3—C12—C13	113.3 (2)
C4—C3—H3	119.9	N2—C12—C13	107.02 (19)
C2—C3—H3	119.9	O3—C12—C8	105.82 (18)
C3—C4—C5	120.0 (3)	N2—C12—C8	106.35 (18)
C3—C4—H4	120.0	C13—C12—C8	114.3 (2)
C5—C4—H4	120.0	C12—C13—Cl2	111.07 (17)
C6—C5—C4	122.1 (3)	C12—C13—H13A	109.4
C6—C5—H5	119.0	Cl2—C13—H13A	109.4
C4—C5—H5	119.0	C12—C13—H13B	109.4
C5—C6—C1	117.5 (2)	Cl2—C13—H13B	109.4
C5—C6—C7	121.2 (2)	H13A—C13—H13B	108.0
C1—C6—C7	121.2 (2)	N4—C14—N1	127.2 (2)
N1—C7—C6	109.5 (2)	N4—C14—N2	110.8 (2)
N1—C7—C8	110.5 (2)	N1—C14—N2	121.9 (2)
C6—C7—C8	111.7 (2)	N3—C15—N4	116.1 (2)
N1—C7—H7	112.1 (16)	N3—C15—S1	124.2 (2)
C6—C7—H7	111.0 (16)	N4—C15—S1	119.66 (19)
C8—C7—H7	101.9 (16)	S1—C16—H16A	109.5
C9—C8—C12	113.9 (2)	S1—C16—H16B	109.5
C9—C8—C7	110.8 (2)	H16A—C16—H16B	109.5
C12—C8—C7	110.40 (19)	S1—C16—H16C	109.5
C9—C8—H8	108.1 (15)	H16A—C16—H16C	109.5
C12—C8—H8	107.5 (14)	H16B—C16—H16C	109.5
C7—C8—H8	105.7 (14)	C14—N1—C7	120.7 (2)
O1—C9—O2	124.5 (3)	C14—N1—H1	118.2 (17)
O1—C9—C8	125.5 (3)	C7—N1—H1	117.4 (16)
O2—C9—C8	109.9 (2)	C14—N2—N3	109.23 (18)
O2—C10—C11	107.0 (3)	C14—N2—C12	124.9 (2)
O2—C10—H10A	110.3	N3—N2—C12	125.74 (19)
C11—C10—H10A	110.3	C15—N3—N2	101.43 (19)
O2—C10—H10B	110.3	C14—N4—C15	102.3 (2)
C11—C10—H10B	110.3	C9—O2—C10	118.2 (2)
H10A—C10—H10B	108.6	C12—O3—H3A	111 (2)

C6—C1—C2—C3	−0.1 (5)	N2—C12—C13—Cl2	−175.47 (17)
Cl1—C1—C2—C3	−179.3 (3)	C8—C12—C13—Cl2	−58.0 (2)
C1—C2—C3—C4	−0.4 (5)	C16—S1—C15—N3	12.5 (3)
C2—C3—C4—C5	0.3 (5)	C16—S1—C15—N4	−165.8 (2)
C3—C4—C5—C6	0.3 (5)	N4—C14—N1—C7	−178.5 (2)
C4—C5—C6—C1	−0.7 (4)	N2—C14—N1—C7	4.3 (4)
C4—C5—C6—C7	176.2 (3)	C6—C7—N1—C14	−151.3 (2)
C2—C1—C6—C5	0.6 (4)	C8—C7—N1—C14	−27.9 (3)
Cl1—C1—C6—C5	179.8 (2)	N4—C14—N2—N3	−0.1 (3)
C2—C1—C6—C7	−176.3 (3)	N1—C14—N2—N3	177.5 (2)
Cl1—C1—C6—C7	2.8 (4)	N4—C14—N2—C12	175.4 (2)
C5—C6—C7—N1	30.3 (3)	N1—C14—N2—C12	−7.0 (4)
C1—C6—C7—N1	−152.8 (2)	O3—C12—N2—C14	−82.2 (3)
C5—C6—C7—C8	−92.4 (3)	C13—C12—N2—C14	154.4 (2)
C1—C6—C7—C8	84.5 (3)	C8—C12—N2—C14	31.9 (3)
N1—C7—C8—C9	−74.3 (3)	O3—C12—N2—N3	92.6 (3)
C6—C7—C8—C9	47.9 (3)	C13—C12—N2—N3	−30.8 (3)
N1—C7—C8—C12	52.8 (3)	C8—C12—N2—N3	−153.3 (2)
C6—C7—C8—C12	175.02 (19)	N4—C15—N3—N2	1.9 (3)
C12—C8—C9—O1	−45.3 (3)	S1—C15—N3—N2	−176.39 (19)
C7—C8—C9—O1	79.9 (3)	C14—N2—N3—C15	−1.1 (3)
C12—C8—C9—O2	138.4 (2)	C12—N2—N3—C15	−176.5 (2)
C7—C8—C9—O2	−96.4 (2)	N1—C14—N4—C15	−176.3 (3)
C9—C8—C12—O3	−170.66 (19)	N2—C14—N4—C15	1.2 (3)
C7—C8—C12—O3	64.0 (2)	N3—C15—N4—C14	−2.0 (3)
C9—C8—C12—N2	72.6 (2)	S1—C15—N4—C14	176.38 (19)
C7—C8—C12—N2	−52.8 (2)	O1—C9—O2—C10	−8.7 (4)
C9—C8—C12—C13	−45.3 (3)	C8—C9—O2—C10	167.6 (3)
C7—C8—C12—C13	−170.64 (19)	C11—C10—O2—C9	−157.3 (3)
O3—C12—C13—Cl2	63.3 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···N4ⁱ	0.93 (3)	2.04 (3)	2.969 (3)	172 (2)
O3—H3A···N3ⁱⁱ	0.77 (3)	2.05 (3)	2.806 (3)	170 (3)
C16—H16A···O3ⁱⁱ	0.96	2.47	3.290 (4)	143

Symmetry codes: (i) −x+2, −y+2, −z+1; (ii) −x+2, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₆H₁₈Cl₂N₄O₃S
M_r	417.30
Crystal system, space group	Triclinic, P1
Temperature (K)	292
a, b, c (Å)	8.4534 (14), 10.5082 (17), 12.0846 (19)
α, β, γ (°)	66.660 (3), 79.519 (3), 84.795 (3)
V (Å³)	969.0 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.47
Crystal size (mm)	0.30 × 0.20 × 0.10

Data collection
Diffractometer	Bruker SMART 4K CCD
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	6772, 3759, 2661
R_int	0.025
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.053, 0.141, 1.08
No. of reflections	3759
No. of parameters	249
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.43, −0.33

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009), SHELXTL (Sheldrick, 2008).