2-(1H-Benzotriazol-1-yl)-1-(4-fluoro­benzo­yl)ethyl isonicotinate

Li, J.; Zeng, W.-L.; Wang, M.-H.; Wan, J.

doi:10.1107/S1600536807042900

2-(1H-Benzotriazol-1-yl)-1-(4-fluorobenzoyl)ethyl isonicotinate

J. Li, W.-L. Zeng, M.-H. Wang and J. Wan

Molecules of the title compound, C₂₁H₁₅FN₄O₃, are linked into chains along the b axis by intermolecular C—H

O hydrogen bonds. C—H

N interactions connect the chains into a three-dimensional network. The packing is further stabilized by C—H

π and π–π interactions [centroid–centroid distance 3.689 (2) Å].

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807042900/sj2347sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807042900/sj2347Isup2.hkl Contains datablock I

CCDC reference: 635804

checkCIF report

Key indicators

Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.005 Å
R factor = 0.057
wR factor = 0.156
Data-to-parameter ratio = 14.1

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         C3
PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ...          5
PLAT431_ALERT_2_C Short Inter HL..A Contact  F1     ..  O2      ..       2.95 Ang.

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 C8     = ...          S

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

   4 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
   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

Recently we have reported the structure of 2-(1H-benzotriazol-1-yl)-1-(4-chlorobenzoyl)ethyl isonicotinate (II) (Han et al., 2007). As part of our ongoing studies of triazole derivatives, the title compound, (I), was synthesized and its structure is presented here.

All bond lengths and angles are within normal ranges (Allen et al., 1987) and are comparable with those in the related compound, (II). The benzotriazole system is essentially planar, with a dihedral angle of 0.32 (2)/% between the triazole ring A (N1—N3/C10/C11) and benzene ring B (C10—C15). The mean plane of the benzotriazole group makes dihedral angles of 62.83 (1) and 51.71 (1)/% with the pyridine ring C (N4/C17—C21) and benzene ring D (C1—C6), respectively. The dihedral angle between the latter two aromatic C and D rings is 65.51 (2)/%.

In the crystal structure, molecules are linked into chains along the b axis by intermolecular C9—H9A···O1 and C15—H15B···O1 hydrogen bonds. C12—H12A···N4 interactions connect the chains into three-dimensional network (Fig. 2). The packing is further stabilized by a C—H···Cg1 (Table 1) interaction, Cg1 is the centroid of the C10···C15 ring. The distance of 3.689 /%A between the centroids of the triazole and pyridine rings with the symmetry code (1/2 - x, -1/2 + y, z) suggests a possible π-π interaction

Related literature top

For a related structure, see: Han et al. (2007). For reference structural data, see: Allen et al. (1987).

Experimental top

The title compound was prepared by the method of Han et al. (2007). Single crystals suitable for X-ray diffraction were obtained by slow evaporation of an ethyl acetate solution at room temperature over a period of one week.

Structure description top

For a related structure, see: Han et al. (2007). For reference structural data, see: Allen et al. (1987).

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT (Siemens, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL (Sheldrick, 1997b) and PLATON (Spek, 2003).

Figures top

	Fig. 1. The structure of the compound (I) showing 50% probability displacement ellipsoids and the atom numbering scheme.
	Fig. 2. A packing diagram of (I), viewed down the c axis. Hydrogen bonds are indicated by dashed lines.

2-(1H-Benzotriazol-1-yl)-1-(4-fluorobenzoyl)ethyl isonicotinate top

Crystal data top

C₂₁H₁₅FN₄O₃	F(000) = 1616
M_r = 390.37	D_x = 1.382 Mg m⁻³
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 1484 reflections
a = 18.475 (2) Å	θ = 2.3–18.3°
b = 10.3014 (13) Å	µ = 0.10 mm⁻¹
c = 19.723 (3) Å	T = 293 K
V = 3753.7 (8) Å³	Needle, colourless
Z = 8	0.40 × 0.05 × 0.03 mm

Data collection top

Siemens SMART 1000 CCD area-detector diffractometer	3706 independent reflections
Radiation source: fine-focus sealed tube	1930 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.073
Detector resolution: 8.33 pixels mm^-1	θ_max = 26.0°, θ_min = 2.1°
ω scans	h = −22→22
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −12→11
T_min = 0.960, T_max = 0.997	l = −24→19
19822 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)] = 0.057	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.156	H-atom parameters constrained
S = 0.94	w = 1/[σ²(F_o²) + (0.0656P)² + 0.9453P] where P = (F_o² + 2F_c²)/3
3706 reflections	(Δ/σ)_max < 0.001
262 parameters	Δρ_max = 0.14 e Å⁻³
0 restraints	Δρ_min = −0.14 e Å⁻³

Crystal data top

C₂₁H₁₅FN₄O₃	V = 3753.7 (8) Å³
M_r = 390.37	Z = 8
Orthorhombic, Pbca	Mo Kα radiation
a = 18.475 (2) Å	µ = 0.10 mm⁻¹
b = 10.3014 (13) Å	T = 293 K
c = 19.723 (3) Å	0.40 × 0.05 × 0.03 mm

Data collection top

Siemens SMART 1000 CCD area-detector diffractometer	3706 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1930 reflections with I > 2σ(I)
T_min = 0.960, T_max = 0.997	R_int = 0.073
19822 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.057	0 restraints
wR(F²) = 0.156	H-atom parameters constrained
S = 0.94	Δρ_max = 0.14 e Å⁻³
3706 reflections	Δρ_min = −0.14 e Å⁻³
262 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
O2	0.16082 (10)	0.45024 (19)	0.08610 (9)	0.0548 (5)
N1	0.30549 (13)	0.3692 (2)	0.11244 (11)	0.0514 (6)
C6	0.17406 (14)	0.3606 (3)	0.27131 (13)	0.0457 (7)
C8	0.17486 (15)	0.3570 (3)	0.13831 (12)	0.0496 (7)
H8A	0.1344	0.2959	0.1415	0.060*
O1	0.20182 (14)	0.5415 (2)	0.20452 (10)	0.0775 (7)
F1	0.14705 (13)	0.1940 (2)	0.45729 (9)	0.1040 (8)
N2	0.31636 (15)	0.4500 (3)	0.05856 (12)	0.0663 (7)
C7	0.18444 (16)	0.4281 (3)	0.20601 (13)	0.0509 (7)
C5	0.17641 (17)	0.4344 (3)	0.32980 (14)	0.0621 (8)
H5A	0.1847	0.5232	0.3265	0.074*
N3	0.37415 (16)	0.5183 (3)	0.06951 (14)	0.0735 (8)
C1	0.16128 (17)	0.2295 (3)	0.27654 (14)	0.0631 (9)
H1A	0.1582	0.1790	0.2376	0.076*
C9	0.24246 (16)	0.2864 (3)	0.11506 (13)	0.0533 (8)
H9A	0.2520	0.2148	0.1457	0.064*
H9B	0.2339	0.2503	0.0703	0.064*
C16	0.09670 (18)	0.5097 (3)	0.08663 (15)	0.0611 (8)
C4	0.16677 (17)	0.3796 (4)	0.39278 (15)	0.0691 (9)
H4A	0.1680	0.4298	0.4319	0.083*
O3	0.05007 (13)	0.4850 (3)	0.12680 (13)	0.0993 (9)
N4	0.0783 (2)	0.7918 (3)	−0.07079 (17)	0.0912 (10)
C10	0.35878 (15)	0.3866 (3)	0.15918 (14)	0.0507 (7)
C11	0.40250 (17)	0.4819 (3)	0.13141 (15)	0.0596 (8)
C17	0.09210 (16)	0.6081 (3)	0.03198 (14)	0.0571 (8)
C3	0.15539 (17)	0.2500 (4)	0.39558 (14)	0.0667 (9)
C18	0.14422 (17)	0.6214 (3)	−0.01731 (14)	0.0611 (8)
H18A	0.1853	0.5694	−0.0170	0.073*
C14	0.43413 (19)	0.3756 (4)	0.25411 (17)	0.0789 (11)
H14A	0.4464	0.3406	0.2960	0.095*
C2	0.1529 (2)	0.1726 (3)	0.33972 (16)	0.0749 (10)
H2B	0.1458	0.0836	0.3438	0.090*
C15	0.37350 (18)	0.3308 (3)	0.22210 (15)	0.0639 (9)
H15B	0.3440	0.2673	0.2410	0.077*
C19	0.1344 (2)	0.7133 (3)	−0.06715 (17)	0.0773 (10)
H19A	0.1698	0.7205	−0.1005	0.093*
C12	0.46429 (18)	0.5250 (4)	0.16520 (17)	0.0784 (10)
H12A	0.4945	0.5877	0.1465	0.094*
C13	0.47831 (18)	0.4714 (4)	0.22652 (18)	0.0844 (11)
H13A	0.5185	0.4994	0.2508	0.101*
C21	0.0339 (2)	0.6903 (4)	0.02977 (19)	0.0869 (12)
H21A	−0.0021	0.6859	0.0627	0.104*
C20	0.0296 (2)	0.7797 (4)	−0.0222 (2)	0.0998 (14)
H20A	−0.0102	0.8350	−0.0230	0.120*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O2	0.0634 (13)	0.0589 (13)	0.0421 (11)	0.0086 (10)	0.0004 (9)	0.0122 (9)
N1	0.0660 (16)	0.0480 (15)	0.0402 (14)	0.0042 (12)	−0.0008 (12)	0.0070 (11)
C6	0.0536 (17)	0.0422 (18)	0.0414 (16)	0.0001 (13)	−0.0018 (12)	0.0060 (13)
C8	0.0675 (19)	0.0447 (17)	0.0368 (16)	−0.0024 (14)	−0.0034 (13)	0.0077 (13)
O1	0.137 (2)	0.0401 (13)	0.0549 (13)	−0.0157 (14)	0.0077 (13)	0.0036 (10)
F1	0.1483 (19)	0.1130 (18)	0.0508 (12)	−0.0085 (15)	0.0038 (12)	0.0284 (11)
N2	0.0780 (18)	0.075 (2)	0.0454 (15)	0.0038 (16)	0.0014 (13)	0.0197 (14)
C7	0.0677 (19)	0.0369 (18)	0.0483 (18)	0.0003 (15)	0.0013 (14)	0.0045 (13)
C5	0.091 (2)	0.0508 (19)	0.0440 (18)	−0.0044 (17)	−0.0018 (16)	−0.0043 (15)
N3	0.0739 (18)	0.083 (2)	0.0630 (18)	−0.0079 (17)	0.0051 (15)	0.0218 (15)
C1	0.098 (2)	0.050 (2)	0.0415 (17)	−0.0105 (17)	0.0004 (16)	0.0020 (14)
C9	0.073 (2)	0.0443 (18)	0.0424 (16)	0.0017 (15)	−0.0057 (14)	−0.0009 (13)
C16	0.062 (2)	0.071 (2)	0.0502 (19)	0.0072 (18)	−0.0022 (16)	0.0056 (16)
C4	0.090 (2)	0.073 (3)	0.0442 (19)	0.001 (2)	−0.0027 (16)	−0.0060 (17)
O3	0.0814 (16)	0.130 (2)	0.0862 (18)	0.0203 (16)	0.0256 (15)	0.0442 (16)
N4	0.110 (3)	0.086 (2)	0.077 (2)	0.019 (2)	−0.015 (2)	0.0247 (18)
C10	0.0622 (18)	0.0475 (18)	0.0425 (16)	0.0096 (15)	0.0003 (14)	0.0016 (13)
C11	0.0651 (19)	0.069 (2)	0.0453 (18)	−0.0006 (17)	0.0068 (16)	0.0102 (16)
C17	0.0650 (19)	0.061 (2)	0.0454 (17)	0.0086 (17)	−0.0085 (15)	0.0043 (15)
C3	0.082 (2)	0.083 (3)	0.0350 (18)	−0.001 (2)	0.0016 (15)	0.0171 (18)
C18	0.068 (2)	0.063 (2)	0.0514 (19)	0.0053 (17)	−0.0052 (16)	0.0065 (16)
C14	0.075 (2)	0.106 (3)	0.056 (2)	−0.002 (2)	−0.0099 (18)	0.017 (2)
C2	0.118 (3)	0.052 (2)	0.054 (2)	−0.013 (2)	0.0018 (19)	0.0131 (17)
C15	0.072 (2)	0.069 (2)	0.0512 (19)	−0.0052 (18)	−0.0030 (16)	0.0142 (16)
C19	0.097 (3)	0.075 (3)	0.060 (2)	0.005 (2)	−0.0071 (19)	0.0194 (19)
C12	0.068 (2)	0.101 (3)	0.066 (2)	−0.018 (2)	0.0084 (18)	0.013 (2)
C13	0.065 (2)	0.120 (3)	0.068 (2)	−0.018 (2)	−0.0033 (18)	0.006 (2)
C21	0.081 (3)	0.103 (3)	0.077 (3)	0.031 (2)	−0.0013 (19)	0.020 (2)
C20	0.101 (3)	0.104 (3)	0.095 (3)	0.047 (3)	−0.016 (3)	0.021 (3)

Geometric parameters (Å, º) top

O2—C16	1.334 (3)	C4—H4A	0.9300
O2—C8	1.431 (3)	N4—C19	1.316 (4)
N1—C10	1.361 (3)	N4—C20	1.321 (5)
N1—N2	1.365 (3)	C10—C11	1.385 (4)
N1—C9	1.444 (4)	C10—C15	1.394 (4)
C6—C1	1.374 (4)	C11—C12	1.394 (4)
C6—C5	1.382 (4)	C17—C21	1.370 (4)
C6—C7	1.476 (4)	C17—C18	1.375 (4)
C8—C9	1.517 (4)	C3—C2	1.361 (4)
C8—C7	1.533 (4)	C18—C19	1.377 (4)
C8—H8A	0.9800	C18—H18A	0.9300
O1—C7	1.212 (3)	C14—C15	1.366 (4)
F1—C3	1.356 (3)	C14—C13	1.392 (5)
N2—N3	1.297 (3)	C14—H14A	0.9300
C5—C4	1.376 (4)	C2—H2B	0.9300
C5—H5A	0.9300	C15—H15B	0.9300
N3—C11	1.380 (4)	C19—H19A	0.9300
C1—C2	1.386 (4)	C12—C13	1.354 (4)
C1—H1A	0.9300	C12—H12A	0.9300
C9—H9A	0.9700	C13—H13A	0.9300
C9—H9B	0.9700	C21—C20	1.380 (5)
C16—O3	1.198 (3)	C21—H21A	0.9300
C16—C17	1.482 (4)	C20—H20A	0.9300
C4—C3	1.353 (5)

C16—O2—C8	117.6 (2)	N1—C10—C15	133.6 (3)
C10—N1—N2	109.9 (2)	C11—C10—C15	122.0 (3)
C10—N1—C9	129.6 (2)	N3—C11—C10	108.7 (3)
N2—N1—C9	120.4 (2)	N3—C11—C12	130.3 (3)
C1—C6—C5	118.9 (3)	C10—C11—C12	120.9 (3)
C1—C6—C7	123.4 (3)	C21—C17—C18	117.7 (3)
C5—C6—C7	117.7 (3)	C21—C17—C16	119.4 (3)
O2—C8—C9	104.7 (2)	C18—C17—C16	122.9 (3)
O2—C8—C7	109.1 (2)	C4—C3—F1	118.3 (3)
C9—C8—C7	113.4 (2)	C4—C3—C2	123.4 (3)
O2—C8—H8A	109.8	F1—C3—C2	118.3 (3)
C9—C8—H8A	109.8	C17—C18—C19	118.8 (3)
C7—C8—H8A	109.8	C17—C18—H18A	120.6
N3—N2—N1	108.8 (2)	C19—C18—H18A	120.6
O1—C7—C6	120.6 (3)	C15—C14—C13	122.7 (3)
O1—C7—C8	118.0 (2)	C15—C14—H14A	118.7
C6—C7—C8	121.3 (2)	C13—C14—H14A	118.7
C4—C5—C6	121.6 (3)	C3—C2—C1	118.4 (3)
C4—C5—H5A	119.2	C3—C2—H2B	120.8
C6—C5—H5A	119.2	C1—C2—H2B	120.8
N2—N3—C11	108.2 (2)	C14—C15—C10	115.6 (3)
C6—C1—C2	120.2 (3)	C14—C15—H15B	122.2
C6—C1—H1A	119.9	C10—C15—H15B	122.2
C2—C1—H1A	119.9	N4—C19—C18	124.4 (4)
N1—C9—C8	113.0 (2)	N4—C19—H19A	117.8
N1—C9—H9A	109.0	C18—C19—H19A	117.8
C8—C9—H9A	109.0	C13—C12—C11	117.0 (3)
N1—C9—H9B	109.0	C13—C12—H12A	121.5
C8—C9—H9B	109.0	C11—C12—H12A	121.5
H9A—C9—H9B	107.8	C12—C13—C14	121.7 (3)
O3—C16—O2	123.1 (3)	C12—C13—H13A	119.1
O3—C16—C17	125.8 (3)	C14—C13—H13A	119.1
O2—C16—C17	111.1 (3)	C17—C21—C20	118.8 (4)
C3—C4—C5	117.5 (3)	C17—C21—H21A	120.6
C3—C4—H4A	121.3	C20—C21—H21A	120.6
C5—C4—H4A	121.3	N4—C20—C21	124.2 (4)
C19—N4—C20	116.1 (3)	N4—C20—H20A	117.9
N1—C10—C11	104.3 (2)	C21—C20—H20A	117.9

C16—O2—C8—C9	167.5 (2)	N2—N3—C11—C12	179.0 (3)
C16—O2—C8—C7	−70.8 (3)	N1—C10—C11—N3	0.0 (3)
C10—N1—N2—N3	−0.3 (3)	C15—C10—C11—N3	−179.7 (3)
C9—N1—N2—N3	176.9 (2)	N1—C10—C11—C12	−179.3 (3)
C1—C6—C7—O1	−173.5 (3)	C15—C10—C11—C12	1.0 (5)
C5—C6—C7—O1	7.5 (4)	O3—C16—C17—C21	7.9 (5)
C1—C6—C7—C8	5.5 (4)	O2—C16—C17—C21	−171.9 (3)
C5—C6—C7—C8	−173.5 (3)	O3—C16—C17—C18	−172.3 (3)
O2—C8—C7—O1	−22.7 (4)	O2—C16—C17—C18	7.9 (4)
C9—C8—C7—O1	93.6 (3)	C5—C4—C3—F1	178.9 (3)
O2—C8—C7—C6	158.3 (2)	C5—C4—C3—C2	−0.1 (5)
C9—C8—C7—C6	−85.5 (3)	C21—C17—C18—C19	−1.9 (5)
C1—C6—C5—C4	0.4 (5)	C16—C17—C18—C19	178.3 (3)
C7—C6—C5—C4	179.5 (3)	C4—C3—C2—C1	−1.1 (5)
N1—N2—N3—C11	0.4 (3)	F1—C3—C2—C1	179.9 (3)
C5—C6—C1—C2	−1.7 (5)	C6—C1—C2—C3	2.1 (5)
C7—C6—C1—C2	179.2 (3)	C13—C14—C15—C10	0.6 (5)
C10—N1—C9—C8	96.4 (3)	N1—C10—C15—C14	179.8 (3)
N2—N1—C9—C8	−80.3 (3)	C11—C10—C15—C14	−0.6 (5)
O2—C8—C9—N1	65.1 (3)	C20—N4—C19—C18	0.7 (6)
C7—C8—C9—N1	−53.7 (3)	C17—C18—C19—N4	0.8 (5)
C8—O2—C16—O3	−3.0 (5)	N3—C11—C12—C13	179.5 (3)
C8—O2—C16—C17	176.8 (2)	C10—C11—C12—C13	−1.4 (5)
C6—C5—C4—C3	0.5 (5)	C11—C12—C13—C14	1.4 (6)
N2—N1—C10—C11	0.2 (3)	C15—C14—C13—C12	−1.1 (6)
C9—N1—C10—C11	−176.7 (3)	C18—C17—C21—C20	1.4 (5)
N2—N1—C10—C15	179.9 (3)	C16—C17—C21—C20	−178.7 (3)
C9—N1—C10—C15	3.0 (5)	C19—N4—C20—C21	−1.2 (6)
N2—N3—C11—C10	−0.3 (4)	C17—C21—C20—N4	0.1 (7)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9A···O1ⁱ	0.97	2.29	3.247 (4)	167
C12—H12A···N4ⁱⁱ	0.93	2.48	3.386 (5)	164
C13—H13A···O3ⁱⁱⁱ	0.93	2.49	3.185 (5)	132
C15—H15B···O1ⁱ	0.93	2.58	3.309 (4)	136
C1—H1A···Cg1^iv	0.93	3.08	3.811	137

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

Experimental details

Crystal data
Chemical formula	C₂₁H₁₅FN₄O₃
M_r	390.37
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	293
a, b, c (Å)	18.475 (2), 10.3014 (13), 19.723 (3)
V (Å³)	3753.7 (8)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.40 × 0.05 × 0.03

Data collection
Diffractometer	Siemens SMART 1000 CCD area-detector
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.960, 0.997
No. of measured, independent and observed [I > 2σ(I)] reflections	19822, 3706, 1930
R_int	0.073
(sin θ/λ)_max (Å⁻¹)	0.618

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.057, 0.156, 0.94
No. of reflections	3706
No. of parameters	262
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.14, −0.14

Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SHELXS97 (Sheldrick, 1997a), SHELXL97 (Sheldrick, 1997a), SHELXTL (Sheldrick, 1997b) and PLATON (Spek, 2003).