2-(1H-Benzimidazol-1-yl)-1-(2-fur­yl)-3-phenyl­propan-1-one

Özel Güven, Ö.; Erdoğan, T.; Çaylak, N.; Hökelek, T.

doi:10.1107/S1600536807036550

2-(1H-Benzimidazol-1-yl)-1-(2-furyl)-3-phenylpropan-1-one

Ö. Özel Güven, T. Erdoğan, N. Çaylak and T. Hökelek

In the molecule of the title compound, C₂₀H₁₆N₂O₂, the planar benzimidazole system is oriented with respect to the furan and phenyl rings with dihedral angles of 87.41 (10) and 61.65 (5)°, respectively. In the crystal structure, intermolecular C—H

O and C—H

N hydrogen bonds link the molecules to form a network structure.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807036550/xu2303sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807036550/xu2303Isup2.hkl Contains datablock I

CCDC reference: 659102

checkCIF report

Key indicators

Single-crystal X-ray study
T = 298 K
Mean (C-C) = 0.004 Å
R factor = 0.045
wR factor = 0.127
Data-to-parameter ratio = 11.9

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT222_ALERT_3_B Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       4.11 Ratio

Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C8     -   C9      ..       5.15 su
PLAT245_ALERT_2_C U(iso) H6      Smaller than U(eq) C6      by ...       0.01 AngSq
PLAT432_ALERT_2_C Short Inter X...Y Contact  O2     ..  C5      ..       2.92 Ang.

Alert level G
PLAT793_ALERT_1_G Check the Absolute Configuration of C6     = ...          S

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

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   3 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 recent years, the benzimidazole heterocyclic ring system has attracted considerable attention, due to its useful properties for the development of interesting new pharmaceutical compounds (Mann et al., 2001). Some of the substituted benzimidazole derivatives have antitumour, antiviral, antibacterial, anti-inflammatory (Roth et al., 1997; Evans et al., 1996; Chen et al., 1993) and therapeutic (Saito et al., 1993; Awouters et al., 1983; Brandstrom et al., 1985) activities. On the other hand, a series of benzimidazole derivatives are useful for central nervous system disorders (Preston, 1974). In literature, 2-(1H-imidazol-1-yl)-1,3-diphenylpropan-1-one and its derivatives have been reported that they show both high and selective thromboxane A2 receptor antagonist and thromboxane A2 synthase inhibitory activities (Cozzi et al., 1994). The structure determination of the title molecule, (I) was carried out in order to investigate the strength of the hydrogen bonding capability of the benzimidazole heterocyclic ring system.

In the molecule of the title compound (Fig. 1) the bond lengths and angles are generally within normal ranges (Allen et al., 1987). A (O1/C1—C4), B (C8—C13), C(N1/N2/C14/C15/C20) and D (C15—C20) rings are, of course, planar and the dihedral angles between the rings are A/B = 47.64 (11)° and C/D = 1.52 (8)°. Thus, the benzimidazole ring system E (N1/N2/C14—C20) is also planar and it is oriented with respect to rings A and B at dihedral angles of A/E = 87.41 (10)° and B/E = 61.65 (5)°.

In the crystal structure, intermolecular C—H···O and C—H···N hydrogen bonds (Table 1) link the molecules to form a network structure (Fig. 2), in which they seem to be effective in the stabilization of the structure.

Related literature top

For general background, see: Mann et al. (2001); Chen et al. (1993); Evans et al. (1996); Roth et al. (1997); Saito et al. (1993); Awouters et al. (1983); Brandstrom et al. (1985); Preston (1974); Cozzi et al. (1994). For related literature, see: Özel Güven et al. (2007). For bond-length data, see: Allen et al. (1987).

Experimental top

The title compound was synthesized as a byproduct in one-pot reaction from 2-(1H-benzimidazol-1-yl)-1-(furan-2-yl)ethanone (Özel Güven et al., 2007) (0.1 g, 0.44 mmol), hydroxylamine hydrogenchloride (0.037 g, 0.53 mmol), benzyl bromide (0.091 g, 0.53 mmol) and KOH (0.213 g, 3.8 mmol) in DMSO (0.53 ml) and water (0.22 ml). Reaction was completed in half an hour at room temperature by stirring. Then, ethyl acetate (3 ml) and brine (1 ml) were added and the reaction mixture was extracted with ethyl acetate. The organic layer was washed with brine three times, dried, filtered and evaporated. The crude residue was purified by column chromatography and recrystallized from methanol to obtain pink crystals (yield; 28 mg, 20%).

Structure description top

Computing details top

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995); 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).

Figures top

	Fig. 1. The molecular structure of the title molecule with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. A packing diagram of (I). Hydrogen bonds are shown as dashed lines. H atoms not involved in hydrogen bonding have been omitted for clarity [symmetry codes: (') -x, -y, -z; ('') x + 1/2, -y + 1/2, z + 1/2].

2-(1H-Benzimidazol-1-yl)-1-(2-furyl)-3-phenylpropan-1-one top

Crystal data top

C₂₀H₁₆N₂O₂	F(000) = 664
M_r = 316.35	D_x = 1.279 Mg m⁻³
Monoclinic, P2₁/n	Melting point = 426–427 K
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71073 Å
a = 16.3886 (2) Å	Cell parameters from 25 reflections
b = 6.5976 (2) Å	θ = 2.3–19.5°
c = 16.7166 (3) Å	µ = 0.08 mm⁻¹
β = 114.677 (9)°	T = 298 K
V = 1642.42 (13) Å³	Prism, pink
Z = 4	0.35 × 0.25 × 0.20 mm

Data collection top

Enraf–Nonius TurboCAD-4 diffractometer	1884 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.020
Graphite monochromator	θ_max = 26.3°, θ_min = 2.9°
Non–profiled ω scans	h = −20→0
Absorption correction: ψ scan (North et al., 1968)	k = 0→8
T_min = 0.971, T_max = 0.983	l = −18→20
3451 measured reflections	3 standard reflections every 120 min
3334 independent reflections	intensity decay: 1%

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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.127	All H-atom parameters refined
S = 0.99	w = 1/[σ²(F_o²) + (0.0555P)² + 0.2297P] where P = (F_o² + 2F_c²)/3
3334 reflections	(Δ/σ)_max < 0.001
281 parameters	Δρ_max = 0.14 e Å⁻³
0 restraints	Δρ_min = −0.15 e Å⁻³

Crystal data top

C₂₀H₁₆N₂O₂	V = 1642.42 (13) Å³
M_r = 316.35	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 16.3886 (2) Å	µ = 0.08 mm⁻¹
b = 6.5976 (2) Å	T = 298 K
c = 16.7166 (3) Å	0.35 × 0.25 × 0.20 mm
β = 114.677 (9)°

Data collection top

Enraf–Nonius TurboCAD-4 diffractometer	1884 reflections with I > 2σ(I)
Absorption correction: ψ scan (North et al., 1968)	R_int = 0.020
T_min = 0.971, T_max = 0.983	3 standard reflections every 120 min
3451 measured reflections	intensity decay: 1%
3334 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.045	0 restraints
wR(F²) = 0.127	All H-atom parameters refined
S = 0.99	Δρ_max = 0.14 e Å⁻³
3334 reflections	Δρ_min = −0.15 e Å⁻³
281 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
O1	1.16659 (12)	1.0691 (3)	0.07170 (10)	0.0713 (5)
O2	1.25039 (11)	0.9637 (2)	0.24119 (10)	0.0587 (4)
N1	1.06934 (11)	0.9260 (2)	0.26597 (10)	0.0416 (4)
N2	1.01229 (13)	0.6120 (3)	0.24342 (13)	0.0586 (5)
C1	1.13037 (15)	1.1210 (3)	0.12921 (13)	0.0491 (5)
C2	1.05646 (19)	1.2327 (4)	0.08763 (16)	0.0654 (7)
H2	1.0208 (15)	1.281 (3)	0.1103 (15)	0.059 (7)*
C3	1.0455 (3)	1.2498 (5)	−0.00107 (17)	0.0817 (9)
H3	0.997 (2)	1.315 (5)	−0.040 (2)	0.108 (11)*
C4	1.1125 (3)	1.1502 (5)	−0.00629 (18)	0.0827 (9)
H4	1.1326 (18)	1.122 (4)	−0.0526 (18)	0.092 (9)*
C5	1.17906 (14)	1.0521 (3)	0.21829 (13)	0.0435 (5)
C6	1.13654 (13)	1.0859 (3)	0.28278 (12)	0.0408 (5)
H6	1.1044 (11)	1.215 (3)	0.2708 (10)	0.027 (4)*
C7	1.20677 (15)	1.0837 (4)	0.37823 (13)	0.0503 (6)
H71	1.2514 (13)	1.187 (3)	0.3809 (13)	0.057 (6)*
H72	1.2361 (13)	0.952 (3)	0.3899 (13)	0.054 (6)*
C8	1.16775 (13)	1.1282 (3)	0.44258 (12)	0.0475 (5)
C9	1.14102 (18)	1.3217 (4)	0.45064 (17)	0.0668 (7)
H9	1.1472 (17)	1.423 (4)	0.4145 (18)	0.088 (9)*
C10	1.1036 (2)	1.3656 (6)	0.50851 (19)	0.0822 (9)
H10	1.0870 (18)	1.502 (4)	0.5123 (17)	0.085 (9)*
C11	1.09365 (19)	1.2166 (7)	0.56044 (18)	0.0858 (10)
H11	1.0705 (19)	1.237 (5)	0.602 (2)	0.111 (10)*
C12	1.1206 (2)	1.0237 (7)	0.55359 (19)	0.0863 (9)
H12	1.114 (2)	0.919 (4)	0.588 (2)	0.106 (10)*
C13	1.15763 (18)	0.9805 (5)	0.49538 (16)	0.0674 (7)
H13	1.1757 (17)	0.847 (4)	0.4899 (16)	0.084 (9)*
C14	1.08385 (16)	0.7231 (3)	0.26522 (15)	0.0530 (6)
H14	1.1436 (14)	0.672 (3)	0.2790 (13)	0.057 (6)*
C15	0.94413 (13)	0.7514 (3)	0.22835 (12)	0.0453 (5)
C16	0.85217 (15)	0.7207 (4)	0.20142 (15)	0.0567 (6)
H16	0.8277 (15)	0.585 (4)	0.1919 (14)	0.062 (7)*
C17	0.79920 (17)	0.8872 (4)	0.18858 (16)	0.0636 (7)
H17	0.7355 (17)	0.866 (4)	0.1711 (15)	0.079 (7)*
C18	0.83400 (16)	1.0828 (4)	0.20143 (17)	0.0631 (7)
H18	0.7947 (17)	1.201 (4)	0.1940 (17)	0.088 (8)*
C19	0.92461 (15)	1.1180 (4)	0.22888 (15)	0.0521 (6)
H19	0.9489 (14)	1.247 (4)	0.2400 (14)	0.066 (7)*
C20	0.97822 (13)	0.9480 (3)	0.24149 (11)	0.0393 (5)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0881 (12)	0.0851 (12)	0.0518 (10)	−0.0060 (10)	0.0402 (9)	−0.0032 (9)
O2	0.0528 (9)	0.0628 (10)	0.0674 (10)	0.0076 (8)	0.0318 (8)	0.0094 (8)
N1	0.0399 (9)	0.0418 (10)	0.0434 (9)	−0.0024 (8)	0.0176 (7)	0.0033 (8)
N2	0.0565 (12)	0.0452 (11)	0.0743 (13)	−0.0032 (10)	0.0275 (10)	0.0071 (10)
C1	0.0563 (13)	0.0509 (13)	0.0440 (12)	−0.0088 (12)	0.0249 (11)	−0.0027 (10)
C2	0.0739 (17)	0.0653 (17)	0.0517 (14)	0.0044 (15)	0.0210 (13)	0.0042 (13)
C3	0.101 (2)	0.078 (2)	0.0484 (16)	−0.0015 (19)	0.0126 (16)	0.0119 (15)
C4	0.117 (3)	0.085 (2)	0.0481 (16)	−0.014 (2)	0.0369 (17)	−0.0003 (15)
C5	0.0432 (12)	0.0399 (11)	0.0480 (12)	−0.0070 (10)	0.0195 (10)	0.0007 (10)
C6	0.0400 (11)	0.0416 (12)	0.0410 (11)	−0.0025 (10)	0.0170 (9)	0.0029 (9)
C7	0.0432 (12)	0.0614 (16)	0.0436 (12)	−0.0022 (13)	0.0155 (10)	0.0028 (11)
C8	0.0415 (11)	0.0593 (14)	0.0349 (11)	−0.0042 (11)	0.0093 (9)	0.0007 (10)
C9	0.0748 (18)	0.0720 (19)	0.0566 (15)	−0.0004 (15)	0.0304 (14)	0.0013 (14)
C10	0.081 (2)	0.094 (2)	0.0724 (19)	0.0038 (18)	0.0335 (16)	−0.0170 (18)
C11	0.0634 (17)	0.150 (3)	0.0486 (15)	−0.006 (2)	0.0277 (14)	−0.011 (2)
C12	0.083 (2)	0.122 (3)	0.0592 (17)	−0.004 (2)	0.0354 (16)	0.0227 (19)
C13	0.0724 (17)	0.076 (2)	0.0540 (14)	0.0010 (15)	0.0261 (13)	0.0160 (13)
C14	0.0489 (14)	0.0441 (14)	0.0669 (15)	0.0061 (12)	0.0249 (12)	0.0102 (11)
C15	0.0466 (12)	0.0498 (13)	0.0399 (11)	−0.0031 (11)	0.0184 (9)	0.0049 (10)
C16	0.0494 (14)	0.0606 (16)	0.0579 (14)	−0.0130 (13)	0.0200 (11)	0.0029 (12)
C17	0.0427 (14)	0.082 (2)	0.0648 (15)	−0.0060 (14)	0.0208 (12)	0.0016 (14)
C18	0.0493 (15)	0.0658 (18)	0.0775 (17)	0.0058 (13)	0.0296 (13)	−0.0001 (14)
C19	0.0491 (13)	0.0490 (15)	0.0611 (14)	0.0015 (12)	0.0259 (11)	−0.0028 (12)
C20	0.0382 (11)	0.0483 (12)	0.0334 (10)	−0.0022 (10)	0.0171 (8)	0.0020 (9)

Geometric parameters (Å, º) top

O1—C1	1.368 (2)	C9—C10	1.375 (4)
O1—C4	1.344 (3)	C9—H9	0.93 (3)
O2—C5	1.216 (2)	C10—H10	0.95 (3)
N1—C6	1.465 (2)	C11—C10	1.366 (4)
N1—C14	1.361 (3)	C11—C12	1.367 (5)
N2—C14	1.299 (3)	C11—H11	0.93 (3)
N2—C15	1.386 (3)	C12—H12	0.94 (3)
C1—C2	1.338 (3)	C13—C12	1.375 (4)
C2—C3	1.422 (4)	C13—H13	0.94 (3)
C2—H2	0.88 (2)	C14—H14	0.97 (2)
C3—H3	0.90 (3)	C15—C16	1.396 (3)
C4—C3	1.314 (4)	C16—H16	0.97 (2)
C4—H4	0.98 (3)	C17—C16	1.361 (3)
C5—C1	1.438 (3)	C17—C18	1.390 (4)
C6—C5	1.525 (3)	C17—H17	0.97 (2)
C6—C7	1.529 (3)	C18—C19	1.379 (3)
C6—H6	0.979 (17)	C18—H18	0.99 (3)
C7—C8	1.492 (3)	C19—H19	0.93 (2)
C7—H71	0.99 (2)	C20—N1	1.382 (2)
C7—H72	0.97 (2)	C20—C15	1.393 (3)
C8—C9	1.375 (3)	C20—C19	1.385 (3)
C8—C13	1.370 (3)

C4—O1—C1	106.1 (2)	C8—C9—H9	118.3 (17)
C14—N1—C20	105.79 (17)	C10—C9—H9	120.4 (17)
C14—N1—C6	126.14 (18)	C11—C10—C9	120.1 (3)
C20—N1—C6	127.91 (17)	C11—C10—H10	121.7 (17)
C14—N2—C15	103.98 (18)	C9—C10—H10	118.1 (17)
C2—C1—O1	109.7 (2)	C10—C11—C12	119.2 (3)
C2—C1—C5	134.6 (2)	C10—C11—H11	124 (2)
O1—C1—C5	115.6 (2)	C12—C11—H11	116 (2)
C1—C2—C3	106.2 (3)	C11—C12—C13	120.4 (3)
C1—C2—H2	126.6 (15)	C11—C12—H12	120.7 (19)
C3—C2—H2	127.2 (15)	C13—C12—H12	118.9 (19)
C4—C3—C2	106.5 (3)	C8—C13—C12	121.1 (3)
C4—C3—H3	135 (2)	C8—C13—H13	118.2 (16)
C2—C3—H3	119 (2)	C12—C13—H13	120.7 (16)
C3—C4—O1	111.5 (3)	N2—C14—N1	114.6 (2)
C3—C4—H4	135.7 (16)	N2—C14—H14	125.1 (13)
O1—C4—H4	112.8 (16)	N1—C14—H14	120.2 (13)
O2—C5—C1	121.48 (19)	N2—C15—C20	110.44 (17)
O2—C5—C6	120.70 (18)	N2—C15—C16	129.9 (2)
C1—C5—C6	117.77 (19)	C20—C15—C16	119.6 (2)
N1—C6—C5	106.74 (15)	C17—C16—C15	117.7 (2)
N1—C6—C7	111.81 (16)	C17—C16—H16	121.9 (13)
C5—C6—C7	111.68 (17)	C15—C16—H16	120.3 (13)
N1—C6—H6	106.9 (9)	C16—C17—C18	122.1 (2)
C5—C6—H6	110.4 (9)	C16—C17—H17	117.9 (15)
C7—C6—H6	109.2 (9)	C18—C17—H17	120.0 (15)
C8—C7—C6	112.83 (18)	C19—C18—C17	121.5 (2)
C8—C7—H71	111.3 (12)	C19—C18—H18	117.7 (15)
C6—C7—H71	105.1 (12)	C17—C18—H18	120.7 (15)
C8—C7—H72	110.9 (12)	C18—C19—C20	116.2 (2)
C6—C7—H72	108.1 (12)	C18—C19—H19	122.3 (14)
H71—C7—H72	108.2 (16)	C20—C19—H19	121.6 (14)
C13—C8—C9	117.9 (2)	N1—C20—C19	131.96 (19)
C13—C8—C7	121.9 (2)	N1—C20—C15	105.17 (17)
C9—C8—C7	120.2 (2)	C19—C20—C15	122.86 (19)
C8—C9—C10	121.2 (3)

C4—O1—C1—C2	−0.6 (3)	C6—C7—C8—C13	107.3 (3)
C4—O1—C1—C5	−178.9 (2)	C6—C7—C8—C9	−73.0 (3)
C1—O1—C4—C3	0.3 (3)	C13—C8—C9—C10	−1.3 (4)
C14—N1—C6—C5	54.1 (2)	C7—C8—C9—C10	179.0 (2)
C20—N1—C6—C5	−120.7 (2)	C9—C8—C13—C12	1.0 (4)
C14—N1—C6—C7	−68.3 (3)	C7—C8—C13—C12	−179.3 (2)
C20—N1—C6—C7	116.9 (2)	C8—C9—C10—C11	1.1 (4)
C6—N1—C14—N2	−176.05 (17)	C12—C11—C10—C9	−0.5 (4)
C20—N1—C14—N2	−0.3 (3)	C10—C11—C12—C13	0.3 (5)
C15—N2—C14—N1	−0.1 (3)	C8—C13—C12—C11	−0.5 (4)
C14—N2—C15—C20	0.4 (2)	N2—C15—C16—C17	−177.7 (2)
C14—N2—C15—C16	178.7 (2)	C20—C15—C16—C17	0.4 (3)
O1—C1—C2—C3	0.6 (3)	C18—C17—C16—C15	0.0 (4)
C5—C1—C2—C3	178.5 (2)	C16—C17—C18—C19	−0.7 (4)
C1—C2—C3—C4	−0.3 (3)	C17—C18—C19—C20	0.9 (4)
O1—C4—C3—C2	0.0 (3)	C19—C20—N1—C14	−178.3 (2)
O2—C5—C1—C2	−173.7 (2)	C15—C20—N1—C14	0.6 (2)
C6—C5—C1—C2	8.6 (4)	C19—C20—N1—C6	−2.7 (3)
O2—C5—C1—O1	4.1 (3)	C15—C20—N1—C6	176.18 (17)
C6—C5—C1—O1	−173.56 (17)	N1—C20—C15—N2	−0.6 (2)
N1—C6—C5—O2	−98.0 (2)	C19—C20—C15—N2	178.35 (19)
C7—C6—C5—O2	24.5 (3)	N1—C20—C15—C16	−179.07 (17)
N1—C6—C5—C1	79.6 (2)	C19—C20—C15—C16	−0.1 (3)
C7—C6—C5—C1	−157.90 (19)	N1—C20—C19—C18	178.1 (2)
N1—C6—C7—C8	−63.7 (3)	C15—C20—C19—C18	−0.5 (3)
C5—C6—C7—C8	176.73 (19)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C14—H14···O2	0.97 (2)	2.35 (2)	3.250 (3)	154.9 (17)
C19—H19···N2ⁱ	0.92 (3)	2.61 (3)	3.529 (3)	170.4 (18)

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

Experimental details

Crystal data
Chemical formula	C₂₀H₁₆N₂O₂
M_r	316.35
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	298
a, b, c (Å)	16.3886 (2), 6.5976 (2), 16.7166 (3)
β (°)	114.677 (9)
V (Å³)	1642.42 (13)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.35 × 0.25 × 0.20

Data collection
Diffractometer	Enraf–Nonius TurboCAD-4
Absorption correction	ψ scan (North et al., 1968)
T_min, T_max	0.971, 0.983
No. of measured, independent and observed [I > 2σ(I)] reflections	3451, 3334, 1884
R_int	0.020
(sin θ/λ)_max (Å⁻¹)	0.623

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.045, 0.127, 0.99
No. of reflections	3334
No. of parameters	281
H-atom treatment	All H-atom parameters refined
Δρ_max, Δρ_min (e Å⁻³)	0.14, −0.15

Computer programs: CAD-4 EXPRESS (Enraf–Nonius, 1994), CAD-4 EXPRESS, XCAD4 (Harms & Wocadlo, 1995), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999).