1-(4-Chloro­phen­yl)-2-diethyl­amino-9-phenyl-1H-purin-6(9H)-one

Huang, N.-Y.; Zhong, Y.; Wang, W.-Q.; Chen, X.; Yang, J.-S.

doi:10.1107/S1600536807058187

1-(4-Chlorophenyl)-2-diethylamino-9-phenyl-1H-purin-6(9H)-one

N.-Y. Huang, Y. Zhong, W.-Q. Wang, X. Chen and J.-S. Yang

The molecule of the title compound, C₂₁H₂₀ClN₅O, has a planar bicyclic imidazolo[5,4-d]pyrimidine core. The planes of the phenyl and 4-chlorophenyl substituents form angles of 48.24 (11) and 71.34 (8)°, respectively, with the imidazolopyrimidine plane. The structure is stabilized by weak intermolecular C—H

N and C—H

O hydrogen bonds.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807058187/bt2605sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807058187/bt2605Isup2.hkl Contains datablock I

CCDC reference: 672961

checkCIF report

Key indicators

Single-crystal X-ray study
T = 292 K
Mean (C-C) = 0.003 Å
R factor = 0.051
wR factor = 0.126
Data-to-parameter ratio = 17.4

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    N5     -   C20     ..       6.98 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

   1 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
   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

Substituted purine derivatives may be used as potential biologically active compounds or pharmaceuticals (Xu et al., 1995). In recent years we have been developing aza-Wittig reaction for synthesis of heterocycles (Ding et al., 2004). In this context, we have synthesized the title compound, 1-(4-chlorophenyl)-2-(diethylamino)-9-phenyl-1H-purin-6(9H)-one, C₂₁H₂₀ClN₅O; herein we report its crystal and molecular structure.

In the molecule (Fig. 1), the bond lengths and angles are unexceptional. The bicyclic imidazolo[5,4-d]pyrimidine system is almost planar with maximum deviation of -0.023 (2) Å for atom C(8), and the angle between plane N1—C7—N2—C8—C9 and N3—C9—C8—C11—N4—C10 is equal to 2.40 (9)°. The torsion angles C9—C8—C11—O1 and O1—C11—N4—C10 are equal to -173.96 (17)° and 177.36 (16)° respectively. The planes of the phenyl rings C1—C6 and C12—C17 are twisted to imidazolo[5,4-d]pyrimidine system with dihedral angles of 48.24 (11)° and 71.34 (8)° respectively.

As can be seen from the packing diagram (Fig. 2), the structure stabilized by the interactions of C—H···N, C—H···O hydrogen bonds. (Table 1).

Related literature top

Related preparation and biological activity is described by Xu et al. (1995). For related literature, see: Ding et al. (2004).

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT-Plus (Bruker, 2001); data reduction: SAINT-Plus (Bruker, 2001; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXTL (Sheldrick, 2001).

Figures top

	Fig. 1. The molecular structure of the title compound, showing the atom-labeling scheme.
	Fig. 2. The packing in the crystal structure, showing the C—H···O hydrogen bonds as dashed lines.

1-(4-Chlorophenyl)-2-diethylamino-9-phenyl-1H-purin-6(9H)-one top

Crystal data top

C₂₁H₂₀ClN₅O	F(000) = 824
M_r = 393.87	D_x = 1.346 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2876 reflections
a = 13.4911 (12) Å	θ = 2.4–24.6°
b = 8.3947 (8) Å	µ = 0.22 mm⁻¹
c = 17.4615 (16) Å	T = 292 K
β = 100.674 (2)°	Block, colorless
V = 1943.4 (3) Å³	0.30 × 0.20 × 0.20 mm
Z = 4

Data collection top

Bruker SMART 4K CCD area-detector diffractometer	4431 independent reflections
Radiation source: fine-focus sealed tube	2979 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.060
ϕ and ω scans	θ_max = 27.5°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	h = −17→16
T_min = 0.937, T_max = 0.958	k = −9→10
12370 measured reflections	l = −22→21

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)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.126	H-atom parameters constrained
S = 0.94	w = 1/[σ²(F_o²) + (0.063P)²] where P = (F_o² + 2F_c²)/3
4431 reflections	(Δ/σ)_max < 0.001
255 parameters	Δρ_max = 0.25 e Å⁻³
0 restraints	Δρ_min = −0.28 e Å⁻³

Crystal data top

C₂₁H₂₀ClN₅O	V = 1943.4 (3) Å³
M_r = 393.87	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 13.4911 (12) Å	µ = 0.22 mm⁻¹
b = 8.3947 (8) Å	T = 292 K
c = 17.4615 (16) Å	0.30 × 0.20 × 0.20 mm
β = 100.674 (2)°

Data collection top

Bruker SMART 4K CCD area-detector diffractometer	4431 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	2979 reflections with I > 2σ(I)
T_min = 0.937, T_max = 0.958	R_int = 0.060
12370 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.051	0 restraints
wR(F²) = 0.126	H-atom parameters constrained
S = 0.94	Δρ_max = 0.25 e Å⁻³
4431 reflections	Δρ_min = −0.28 e Å⁻³
255 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	0.58415 (14)	0.3486 (3)	0.20261 (13)	0.0582 (5)
H1	0.5596	0.3982	0.1553	0.070*
C2	0.53522 (17)	0.3669 (3)	0.26485 (18)	0.0746 (7)
H2	0.4765	0.4274	0.2590	0.089*
C3	0.5719 (2)	0.2976 (3)	0.33449 (17)	0.0799 (8)
H3	0.5392	0.3120	0.3764	0.096*
C4	0.65702 (19)	0.2066 (3)	0.34277 (13)	0.0803 (8)
H4	0.6819	0.1589	0.3905	0.096*
C5	0.70677 (15)	0.1844 (3)	0.28114 (12)	0.0604 (6)
H5	0.7645	0.1218	0.2870	0.073*
C6	0.66952 (12)	0.2562 (2)	0.21152 (10)	0.0415 (4)
C7	0.67228 (13)	0.1855 (2)	0.07248 (11)	0.0487 (5)
H7	0.6030	0.1706	0.0582	0.058*
C8	0.82762 (12)	0.1991 (2)	0.06945 (10)	0.0387 (4)
C9	0.81868 (12)	0.2404 (2)	0.14362 (10)	0.0374 (4)
C10	0.98288 (12)	0.2842 (2)	0.18586 (10)	0.0374 (4)
C11	0.92328 (13)	0.2069 (2)	0.04677 (10)	0.0380 (4)
C12	1.09679 (12)	0.2904 (2)	0.08956 (10)	0.0374 (4)
C13	1.15729 (13)	0.1696 (2)	0.07040 (10)	0.0420 (4)
H13	1.1372	0.0639	0.0722	0.050*
C14	1.24807 (13)	0.2069 (2)	0.04857 (10)	0.0471 (5)
H14	1.2897	0.1268	0.0357	0.056*
C15	1.27571 (13)	0.3642 (2)	0.04617 (10)	0.0459 (5)
C16	1.21545 (13)	0.4855 (2)	0.06383 (10)	0.0453 (4)
H16	1.2352	0.5912	0.0611	0.054*
C17	1.12478 (13)	0.4475 (2)	0.08573 (10)	0.0418 (4)
H17	1.0829	0.5279	0.0978	0.050*
C18	1.15040 (13)	0.2194 (2)	0.26058 (11)	0.0473 (5)
H18A	1.1490	0.1454	0.2177	0.057*
H18B	1.1431	0.1579	0.3063	0.057*
C19	1.25144 (15)	0.3020 (3)	0.27618 (14)	0.0743 (7)
H19A	1.2586	0.3657	0.2319	0.111*
H19B	1.3042	0.2237	0.2854	0.111*
H19C	1.2558	0.3690	0.3212	0.111*
C20	1.04109 (15)	0.4238 (3)	0.30744 (12)	0.0630 (6)
H20A	0.9879	0.4987	0.2872	0.076*
H20B	1.1006	0.4853	0.3291	0.076*
C21	1.00919 (19)	0.3313 (3)	0.37215 (13)	0.0861 (8)
H21A	0.9473	0.2763	0.3526	0.129*
H21B	0.9992	0.4030	0.4129	0.129*
H21C	1.0606	0.2554	0.3924	0.129*
Cl1	1.38876 (4)	0.41047 (8)	0.01601 (3)	0.0754 (2)
N1	0.71771 (10)	0.23172 (18)	0.14620 (8)	0.0428 (4)
N2	0.73402 (11)	0.16444 (19)	0.02426 (9)	0.0472 (4)
N3	0.89291 (10)	0.28148 (17)	0.20361 (8)	0.0408 (4)
N4	1.00083 (10)	0.25229 (16)	0.11090 (8)	0.0370 (3)
N5	1.06403 (11)	0.32839 (18)	0.24143 (8)	0.0437 (4)
O1	0.94322 (9)	0.18633 (15)	−0.01760 (7)	0.0475 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0452 (12)	0.0614 (14)	0.0699 (14)	0.0045 (9)	0.0153 (10)	0.0086 (11)
C2	0.0559 (14)	0.0691 (16)	0.108 (2)	0.0071 (11)	0.0394 (14)	−0.0124 (15)
C3	0.0720 (17)	0.103 (2)	0.0773 (18)	−0.0217 (15)	0.0456 (15)	−0.0334 (16)
C4	0.0768 (18)	0.123 (2)	0.0439 (13)	−0.0107 (15)	0.0184 (12)	−0.0016 (13)
C5	0.0483 (12)	0.0885 (16)	0.0450 (12)	0.0071 (11)	0.0100 (9)	0.0057 (11)
C6	0.0313 (9)	0.0529 (11)	0.0415 (10)	−0.0029 (8)	0.0097 (8)	−0.0020 (8)
C7	0.0340 (10)	0.0687 (13)	0.0414 (11)	−0.0069 (9)	0.0013 (8)	0.0012 (9)
C8	0.0345 (9)	0.0461 (11)	0.0346 (9)	−0.0039 (7)	0.0038 (7)	0.0010 (8)
C9	0.0335 (9)	0.0459 (11)	0.0320 (9)	−0.0021 (7)	0.0042 (7)	0.0013 (8)
C10	0.0362 (9)	0.0396 (10)	0.0359 (10)	−0.0009 (7)	0.0053 (8)	−0.0007 (8)
C11	0.0400 (10)	0.0393 (10)	0.0347 (10)	−0.0021 (7)	0.0071 (8)	0.0003 (8)
C12	0.0328 (9)	0.0450 (11)	0.0344 (9)	−0.0034 (7)	0.0066 (7)	−0.0001 (8)
C13	0.0430 (10)	0.0409 (10)	0.0420 (10)	−0.0016 (8)	0.0074 (8)	−0.0006 (8)
C14	0.0383 (10)	0.0579 (13)	0.0456 (11)	0.0040 (9)	0.0094 (8)	−0.0054 (9)
C15	0.0325 (9)	0.0667 (13)	0.0382 (10)	−0.0076 (9)	0.0060 (8)	0.0016 (9)
C16	0.0463 (11)	0.0475 (11)	0.0412 (10)	−0.0110 (9)	0.0060 (8)	0.0039 (8)
C17	0.0427 (10)	0.0413 (11)	0.0413 (10)	0.0006 (8)	0.0076 (8)	−0.0007 (8)
C18	0.0380 (10)	0.0579 (12)	0.0443 (11)	−0.0025 (8)	0.0031 (8)	0.0064 (9)
C19	0.0405 (12)	0.0941 (19)	0.0826 (18)	−0.0129 (11)	−0.0036 (12)	0.0131 (13)
C20	0.0507 (12)	0.0825 (16)	0.0513 (13)	−0.0017 (11)	−0.0023 (10)	−0.0180 (11)
C21	0.0800 (17)	0.133 (2)	0.0433 (13)	0.0161 (16)	0.0075 (12)	−0.0050 (14)
Cl1	0.0437 (3)	0.1085 (5)	0.0790 (4)	−0.0164 (3)	0.0242 (3)	0.0026 (3)
N1	0.0312 (8)	0.0601 (10)	0.0369 (8)	−0.0022 (7)	0.0060 (6)	0.0012 (7)
N2	0.0385 (9)	0.0640 (11)	0.0376 (8)	−0.0082 (7)	0.0032 (7)	−0.0024 (7)
N3	0.0337 (8)	0.0550 (10)	0.0334 (8)	−0.0005 (7)	0.0057 (6)	−0.0015 (7)
N4	0.0323 (8)	0.0443 (9)	0.0346 (8)	−0.0036 (6)	0.0068 (6)	−0.0018 (6)
N5	0.0367 (8)	0.0555 (10)	0.0364 (8)	−0.0009 (7)	0.0002 (6)	−0.0062 (7)
O1	0.0461 (7)	0.0629 (9)	0.0353 (7)	−0.0066 (6)	0.0125 (6)	−0.0058 (6)

Geometric parameters (Å, º) top

C1—C6	1.373 (3)	C12—C13	1.381 (2)
C1—C2	1.381 (3)	C12—N4	1.448 (2)
C1—H1	0.9300	C13—C14	1.384 (2)
C2—C3	1.356 (4)	C13—H13	0.9300
C2—H2	0.9300	C14—C15	1.375 (3)
C3—C4	1.364 (3)	C14—H14	0.9300
C3—H3	0.9300	C15—C16	1.373 (3)
C4—C5	1.382 (3)	C15—Cl1	1.7469 (17)
C4—H4	0.9300	C16—C17	1.385 (2)
C5—C6	1.366 (3)	C16—H16	0.9300
C5—H5	0.9300	C17—H17	0.9300
C6—N1	1.428 (2)	C18—N5	1.470 (2)
C7—N2	1.302 (2)	C18—C19	1.508 (3)
C7—N1	1.375 (2)	C18—H18A	0.9700
C7—H7	0.9300	C18—H18B	0.9700
C8—C9	1.367 (2)	C19—H19A	0.9600
C8—N2	1.390 (2)	C19—H19B	0.9600
C8—C11	1.420 (2)	C19—H19C	0.9600
C9—N3	1.353 (2)	C20—N5	1.482 (2)
C9—N1	1.373 (2)	C20—C21	1.498 (3)
C10—N3	1.307 (2)	C20—H20A	0.9700
C10—N5	1.373 (2)	C20—H20B	0.9700
C10—N4	1.400 (2)	C21—H21A	0.9600
C11—O1	1.2155 (19)	C21—H21B	0.9600
C11—N4	1.435 (2)	C21—H21C	0.9600
C12—C17	1.377 (2)

C6—C1—C2	119.1 (2)	C16—C15—Cl1	119.28 (15)
C6—C1—H1	120.4	C14—C15—Cl1	118.65 (15)
C2—C1—H1	120.4	C15—C16—C17	118.74 (17)
C3—C2—C1	120.6 (2)	C15—C16—H16	120.6
C3—C2—H2	119.7	C17—C16—H16	120.6
C1—C2—H2	119.7	C12—C17—C16	119.91 (16)
C2—C3—C4	119.7 (2)	C12—C17—H17	120.0
C2—C3—H3	120.2	C16—C17—H17	120.0
C4—C3—H3	120.2	N5—C18—C19	114.00 (17)
C3—C4—C5	120.9 (2)	N5—C18—H18A	108.8
C3—C4—H4	119.6	C19—C18—H18A	108.8
C5—C4—H4	119.6	N5—C18—H18B	108.8
C6—C5—C4	118.8 (2)	C19—C18—H18B	108.8
C6—C5—H5	120.6	H18A—C18—H18B	107.6
C4—C5—H5	120.6	C18—C19—H19A	109.5
C5—C6—C1	120.82 (18)	C18—C19—H19B	109.5
C5—C6—N1	120.01 (16)	H19A—C19—H19B	109.5
C1—C6—N1	119.15 (17)	C18—C19—H19C	109.5
N2—C7—N1	114.60 (15)	H19A—C19—H19C	109.5
N2—C7—H7	122.7	H19B—C19—H19C	109.5
N1—C7—H7	122.7	N5—C20—C21	115.92 (19)
C9—C8—N2	111.13 (15)	N5—C20—H20A	108.3
C9—C8—C11	119.79 (15)	C21—C20—H20A	108.3
N2—C8—C11	128.91 (16)	N5—C20—H20B	108.3
N3—C9—C8	127.98 (15)	C21—C20—H20B	108.3
N3—C9—N1	125.78 (15)	H20A—C20—H20B	107.4
C8—C9—N1	106.24 (14)	C20—C21—H21A	109.5
N3—C10—N5	119.41 (15)	C20—C21—H21B	109.5
N3—C10—N4	123.17 (15)	H21A—C21—H21B	109.5
N5—C10—N4	117.32 (14)	C20—C21—H21C	109.5
O1—C11—C8	128.30 (16)	H21A—C21—H21C	109.5
O1—C11—N4	120.33 (15)	H21B—C21—H21C	109.5
C8—C11—N4	111.31 (14)	C9—N1—C7	104.90 (14)
C17—C12—C13	120.78 (16)	C9—N1—C6	128.28 (14)
C17—C12—N4	119.37 (15)	C7—N1—C6	126.74 (14)
C13—C12—N4	119.80 (15)	C7—N2—C8	103.13 (15)
C12—C13—C14	119.57 (17)	C10—N3—C9	114.05 (14)
C12—C13—H13	120.2	C10—N4—C11	123.56 (13)
C14—C13—H13	120.2	C10—N4—C12	121.07 (13)
C15—C14—C13	118.96 (17)	C11—N4—C12	114.53 (13)
C15—C14—H14	120.5	C10—N5—C18	119.17 (15)
C13—C14—H14	120.5	C10—N5—C20	116.20 (15)
C16—C15—C14	122.02 (16)	C18—N5—C20	115.46 (15)

C6—C1—C2—C3	1.4 (3)	C5—C6—N1—C9	−47.3 (3)
C1—C2—C3—C4	−1.1 (4)	C1—C6—N1—C9	134.52 (19)
C2—C3—C4—C5	0.2 (4)	C5—C6—N1—C7	128.9 (2)
C3—C4—C5—C6	0.4 (4)	C1—C6—N1—C7	−49.2 (3)
C4—C5—C6—C1	−0.1 (3)	N1—C7—N2—C8	0.1 (2)
C4—C5—C6—N1	−178.23 (19)	C9—C8—N2—C7	−0.1 (2)
C2—C1—C6—C5	−0.8 (3)	C11—C8—N2—C7	−175.35 (18)
C2—C1—C6—N1	177.37 (18)	N5—C10—N3—C9	178.26 (15)
N2—C8—C9—N3	179.92 (17)	N4—C10—N3—C9	1.8 (2)
C11—C8—C9—N3	−4.4 (3)	C8—C9—N3—C10	1.7 (3)
N2—C8—C9—N1	0.2 (2)	N1—C9—N3—C10	−178.59 (16)
C11—C8—C9—N1	175.87 (15)	N3—C10—N4—C11	−2.7 (3)
C9—C8—C11—O1	−173.96 (17)	N5—C10—N4—C11	−179.20 (15)
N2—C8—C11—O1	0.9 (3)	N3—C10—N4—C12	166.22 (15)
C9—C8—C11—N4	3.1 (2)	N5—C10—N4—C12	−10.3 (2)
N2—C8—C11—N4	177.92 (16)	O1—C11—N4—C10	177.36 (16)
C17—C12—C13—C14	1.3 (3)	C8—C11—N4—C10	0.0 (2)
N4—C12—C13—C14	178.75 (15)	O1—C11—N4—C12	7.8 (2)
C12—C13—C14—C15	−0.3 (3)	C8—C11—N4—C12	−169.53 (14)
C13—C14—C15—C16	−0.8 (3)	C17—C12—N4—C10	−66.8 (2)
C13—C14—C15—Cl1	−178.29 (14)	C13—C12—N4—C10	115.73 (18)
C14—C15—C16—C17	0.9 (3)	C17—C12—N4—C11	103.11 (18)
Cl1—C15—C16—C17	178.35 (13)	C13—C12—N4—C11	−74.41 (19)
C13—C12—C17—C16	−1.2 (3)	N3—C10—N5—C18	124.16 (18)
N4—C12—C17—C16	−178.68 (15)	N4—C10—N5—C18	−59.2 (2)
C15—C16—C17—C12	0.1 (3)	N3—C10—N5—C20	−21.3 (2)
N3—C9—N1—C7	−179.88 (17)	N4—C10—N5—C20	155.38 (16)
C8—C9—N1—C7	−0.12 (19)	C19—C18—N5—C10	142.09 (18)
N3—C9—N1—C6	−3.0 (3)	C19—C18—N5—C20	−72.2 (2)
C8—C9—N1—C6	176.78 (16)	C21—C20—N5—C10	82.7 (2)
N2—C7—N1—C9	0.0 (2)	C21—C20—N5—C18	−64.0 (2)
N2—C7—N1—C6	−176.93 (17)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C21—H21A···N3	0.96	2.57	3.096 (3)	115
C16—H16···N2ⁱ	0.93	2.61	3.443 (2)	149
C13—H13···O1ⁱⁱ	0.93	2.47	3.340 (2)	155
C3—H3···O1ⁱⁱⁱ	0.93	2.45	3.371 (3)	172

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

Experimental details

Crystal data
Chemical formula	C₂₁H₂₀ClN₅O
M_r	393.87
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	292
a, b, c (Å)	13.4911 (12), 8.3947 (8), 17.4615 (16)
β (°)	100.674 (2)
V (Å³)	1943.4 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.22
Crystal size (mm)	0.30 × 0.20 × 0.20

Data collection
Diffractometer	Bruker SMART 4K CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2003)
T_min, T_max	0.937, 0.958
No. of measured, independent and observed [I > 2σ(I)] reflections	12370, 4431, 2979
R_int	0.060
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.051, 0.126, 0.94
No. of reflections	4431
No. of parameters	255
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.25, −0.28

Computer programs: SMART (Bruker, 2001), SAINT-Plus (Bruker, 2001), SAINT-Plus (Bruker, 2001, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), PLATON (Spek, 2003), SHELXTL (Sheldrick, 2001).