3-Cyclo­hexyl­sulfonyl-5-iodo-2,7-dimethyl-1-benzofuran

Seo, P.J.; Choi, H.D.; Son, B.W.; Lee, U.

doi:10.1107/S1600536811027395

organic compounds

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ISSN: 2056-9890

Volume 67| Part 8| August 2011| Page o2053

doi:10.1107/S1600536811027395

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3-Cyclohexylsulfonyl-5-iodo-2,7-dimethyl-1-benzofuran

Pil Ja Seo,^a Hong Dae Choi,^a Byeng Wha Son ^b and Uk Lee ^b ^*

^aDepartment of Chemistry, Dongeui University, San 24 Kaya-dong Busanjin-gu, Busan 614-714, Republic of Korea, and ^bDepartment of Chemistry, Pukyong National University, 599-1 Daeyeon 3-dong, Nam-gu, Busan 608-737, Republic of Korea
^*Correspondence e-mail: uklee@pknu.ac.kr

(Received 6 July 2011; accepted 8 July 2011; online 16 July 2011)

In the title compound, C₁₆H₁₉IO₃S, the cyclohexyl ring adopts a chair conformation. In the crystal, pairs of intermolecular I⋯O contacts [3.269 (2) Å] link the molecules into inversion dimers. These dimers are further stabilized by a slipped π–π interaction between the benzene and furan rings of adjacent molecules [centroid–centroid distance = 3.701 (3) Å, interplanar distance = 3.372 (3) Å and slippage = 1.525 (3) Å].

Related literature

For the pharmacological activity of benzofuran compounds, see: Aslam et al. (2009 ); Galal et al. (2009 ); Khan et al. (2005 ). For natural products with benzofuran rings, see: Akgul & Anil (2003 ); Soekamto et al. (2003 ). For structural studies of related 3-cyclohexylsulfonyl-5-halo-2-methyl-1-benzofuran derivatives, see: Choi et al. (2011a ,b ,c ). For a review on halogen bonding, see: Politzer et al. (2007 ).

Experimental

Crystal data

C₁₆H₁₉IO₃S
M_r = 418.27
Triclinic, $[P \overline 1]$
a = 6.8643 (2) Å
b = 8.4981 (2) Å
c = 14.2323 (3) Å
α = 102.512 (1)°
β = 99.846 (1)°
γ = 92.092 (1)°
V = 796.23 (3) Å³
Z = 2
Mo Kα radiation
μ = 2.15 mm⁻¹
T = 173 K
0.24 × 0.16 × 0.14 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.629, T_max = 0.759
15021 measured reflections
3997 independent reflections
3753 reflections with I > 2σ(I)
R_int = 0.035

Refinement

R[F² > 2σ(F²)] = 0.023
wR(F²) = 0.058
S = 1.06
3997 reflections
192 parameters
H-atom parameters constrained
Δρ_max = 0.68 e Å⁻³
Δρ_min = −0.63 e Å⁻³

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997 ) and DIAMOND (Brandenburg, 1998 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811027395/zl2384sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811027395/zl2384Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811027395/zl2384Isup3.cml

checkCIF report

Comment top

Recently, many compounds containing a benzofuran moiety have drawn much attention owing to their valuable pharmacological properties such as antibacterial and antifungal, antitumor and antiviral, and antimicrobial activities (Aslam et al., 2009, Galal et al., 2009, Khan et al., 2005). These benzofuran derivatives occur in a wide range of natural products (Akgul & Anil, 2003; Soekamto et al., 2003). As a part of our ongoing study of the substituent effect on the solid state structures of 3-cyclohexylsulfonyl-5-halo-2-methyl-1-benzofuran analogues (Choi et al., 2011a,b,c), we report herein the crystal structure of the title compound.

In the title molecule (Fig. 1), the benzofuran unit is essentially planar, with a mean deviation of 0.007 (2) Å from the least-squares plane defined by the nine constituent atoms. The cyclohexyl ring is in the chair form. The molecular packing (Fig. 2) is stabilized by I···O halogen-bondings between the iodine and the O atom of the sulfonyl group [I1···O2ⁱⁱ = 3.269 (2) Å; C4—11···O2ⁱⁱ = 168.48 (6)°] (Politzer et al., 2007). The crystal packing (Fig. 2) is further stabilized by a weak slipped π···π interaction between the benzene and furan rings of adjacent molecules, with a Cg1···Cg2ⁱ distance of 3.701 (3) Å and an interplanar distance of 3.372 (3) Å resulting in a slippage of 1.525 (3) Å (Cg1 and Cg2 are the centroids of the C2–C7 benzene ring and the C1/C2/C7/O1/C8 furan ring, respectively, see Fig. 2 for symmetry codes).

Related literature top

For the pharmacological activity of benzofuran compounds, see: Aslam et al. (2009); Galal et al. (2009); Khan et al. (2005). For natural products with benzofuran rings, see: Akgul & Anil (2003); Soekamto et al. (2003). For structural studies of related 3-cyclohexylsulfonyl-5-halo-2-methyl-1-benzofuran derivatives, see: Choi et al. (2011a,b,c). For a review on halogen bonding, see: Politzer et al. (2007).

Experimental top

77% 3-chloroperoxybenzoic acid (426 mg, 1.9 mmol) was added in small portions to a stirred solution of 3-cyclohexylsulfanyl-5-iodo-2,7-dimethyl-1-benzofuran (347 mg, 0.9 mmol) in dichloromethane (35 mL) at 273 K. After being stirred at room temperature for 8h, the mixture was washed with saturated sodium bicarbonate solution and the organic layer was separated, dried over magnesium sulfate, filtered and concentrated at reduced pressure. The residue was purified by column chromatography (hexane–ethyl acetate, 4:1 v/v) to afford the title compound as a colorless solid [yield 71%, m.p. 441–442 K; R_f = 0.63 (hexane–ethyl acetate, 4:1 v/v)]. Single crystals suitable for X-ray diffraction were prepared by slow evaporation of a solution of the title compound in acetone at room temperature.

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 1998); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound with the atom numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. H atoms are presented as a small spheres of arbitrary radius.
	Fig. 2. A view of the I···O and π···π interactions (dotted lines) in the crystal structure of the title compound. [Symmetry codes: (i) - x + 1, - y + 2, - z + 1; (ii) - x, - y + 1, - z + 1.]

3-Cyclohexylsulfonyl-5-iodo-2,7-dimethyl-1-benzofuran top

Crystal data top

C₁₆H₁₉IO₃S	Z = 2
M_r = 418.27	F(000) = 416
Triclinic, P1	D_x = 1.745 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.8643 (2) Å	Cell parameters from 8926 reflections
b = 8.4981 (2) Å	θ = 2.5–28.4°
c = 14.2323 (3) Å	µ = 2.15 mm⁻¹
α = 102.512 (1)°	T = 173 K
β = 99.846 (1)°	Block, colourless
γ = 92.092 (1)°	0.24 × 0.16 × 0.14 mm
V = 796.23 (3) Å³

Data collection top

Bruker SMART APEXII CCD diffractometer	3997 independent reflections
Radiation source: rotating anode	3753 reflections with I > 2σ(I)
Graphite multilayer monochromator	R_int = 0.035
Detector resolution: 10.0 pixels mm^-1	θ_max = 28.4°, θ_min = 1.5°
ϕ and ω scans	h = −7→9
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −11→11
T_min = 0.629, T_max = 0.759	l = −19→18
15021 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)] = 0.023	Hydrogen site location: difference Fourier map
wR(F²) = 0.058	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.0291P)² + 0.2895P] where P = (F_o² + 2F_c²)/3
3997 reflections	(Δ/σ)_max = 0.003
192 parameters	Δρ_max = 0.68 e Å⁻³
0 restraints	Δρ_min = −0.63 e Å⁻³

Crystal data top

C₁₆H₁₉IO₃S	γ = 92.092 (1)°
M_r = 418.27	V = 796.23 (3) Å³
Triclinic, P1	Z = 2
a = 6.8643 (2) Å	Mo Kα radiation
b = 8.4981 (2) Å	µ = 2.15 mm⁻¹
c = 14.2323 (3) Å	T = 173 K
α = 102.512 (1)°	0.24 × 0.16 × 0.14 mm
β = 99.846 (1)°

Data collection top

Bruker SMART APEXII CCD diffractometer	3997 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	3753 reflections with I > 2σ(I)
T_min = 0.629, T_max = 0.759	R_int = 0.035
15021 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.023	0 restraints
wR(F²) = 0.058	H-atom parameters constrained
S = 1.06	Δρ_max = 0.68 e Å⁻³
3997 reflections	Δρ_min = −0.63 e Å⁻³
192 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
I1	0.227778 (18)	0.565947 (15)	0.643317 (9)	0.02648 (5)
S1	0.19017 (7)	0.68116 (6)	0.21668 (4)	0.02476 (10)
O1	0.6820 (2)	0.89122 (16)	0.38987 (10)	0.0237 (3)
O2	0.0181 (2)	0.67742 (19)	0.26177 (12)	0.0329 (3)
O3	0.1832 (3)	0.76329 (19)	0.13777 (12)	0.0350 (4)
C1	0.3897 (3)	0.7652 (2)	0.30960 (14)	0.0224 (4)
C2	0.4132 (3)	0.7461 (2)	0.40933 (14)	0.0211 (4)
C3	0.3023 (3)	0.6713 (2)	0.46236 (14)	0.0234 (4)
H3	0.1761	0.6163	0.4336	0.028*
C4	0.3852 (3)	0.6808 (2)	0.55982 (14)	0.0229 (4)
C5	0.5707 (3)	0.7612 (2)	0.60332 (14)	0.0231 (4)
H5	0.6207	0.7642	0.6702	0.028*
C6	0.6829 (3)	0.8363 (2)	0.55159 (15)	0.0225 (4)
C7	0.5962 (3)	0.8262 (2)	0.45489 (14)	0.0211 (4)
C8	0.5545 (3)	0.8523 (2)	0.30207 (14)	0.0238 (4)
C9	0.8856 (3)	0.9191 (3)	0.59487 (16)	0.0278 (4)
H9A	0.9151	0.9214	0.6650	0.042*
H9B	0.8892	1.0300	0.5855	0.042*
H9C	0.9846	0.8600	0.5623	0.042*
C10	0.6225 (3)	0.9118 (3)	0.22258 (16)	0.0311 (4)
H10A	0.6478	1.0297	0.2421	0.047*
H10B	0.5201	0.8827	0.1633	0.047*
H10C	0.7449	0.8628	0.2094	0.047*
C11	0.2463 (3)	0.4764 (2)	0.17566 (14)	0.0252 (4)
H11	0.2952	0.4337	0.2349	0.030*
C12	0.0574 (3)	0.3736 (3)	0.11981 (17)	0.0342 (5)
H12A	−0.0438	0.3806	0.1622	0.041*
H12B	0.0030	0.4145	0.0614	0.041*
C13	0.1052 (4)	0.1980 (3)	0.0884 (2)	0.0461 (6)
H13A	0.1485	0.1550	0.1473	0.055*
H13B	−0.0160	0.1324	0.0500	0.055*
C14	0.2662 (4)	0.1825 (3)	0.0274 (2)	0.0446 (6)
H14A	0.2180	0.2151	−0.0346	0.054*
H14B	0.2979	0.0681	0.0112	0.054*
C15	0.4538 (4)	0.2879 (3)	0.08190 (18)	0.0365 (5)
H15A	0.5530	0.2811	0.0385	0.044*
H15B	0.5111	0.2470	0.1399	0.044*
C16	0.4094 (3)	0.4643 (3)	0.11478 (16)	0.0303 (4)
H16A	0.5310	0.5283	0.1541	0.036*
H16B	0.3672	0.5096	0.0567	0.036*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
I1	0.02413 (8)	0.02921 (8)	0.02755 (8)	0.00073 (5)	0.00534 (5)	0.00927 (5)
S1	0.0237 (2)	0.0259 (2)	0.0223 (2)	0.00194 (18)	−0.00089 (18)	0.00417 (18)
O1	0.0210 (7)	0.0248 (7)	0.0242 (7)	−0.0001 (5)	0.0038 (5)	0.0039 (5)
O2	0.0221 (7)	0.0389 (9)	0.0338 (8)	0.0025 (6)	0.0019 (6)	0.0022 (6)
O3	0.0392 (9)	0.0337 (8)	0.0312 (8)	0.0025 (7)	−0.0044 (7)	0.0138 (6)
C1	0.0218 (9)	0.0223 (9)	0.0211 (9)	0.0025 (7)	0.0017 (7)	0.0024 (7)
C2	0.0201 (9)	0.0189 (8)	0.0227 (9)	0.0030 (7)	0.0030 (7)	0.0020 (7)
C3	0.0197 (9)	0.0227 (9)	0.0256 (9)	−0.0006 (7)	0.0022 (7)	0.0024 (7)
C4	0.0226 (9)	0.0216 (9)	0.0254 (9)	0.0019 (7)	0.0064 (7)	0.0054 (7)
C5	0.0224 (9)	0.0237 (9)	0.0224 (9)	0.0041 (7)	0.0017 (7)	0.0046 (7)
C6	0.0204 (9)	0.0183 (8)	0.0257 (9)	0.0030 (7)	0.0009 (7)	0.0010 (7)
C7	0.0206 (9)	0.0189 (8)	0.0239 (9)	0.0021 (7)	0.0056 (7)	0.0039 (7)
C8	0.0249 (9)	0.0223 (9)	0.0230 (9)	0.0046 (7)	0.0025 (7)	0.0036 (7)
C9	0.0202 (9)	0.0300 (10)	0.0302 (10)	−0.0015 (8)	−0.0014 (8)	0.0054 (8)
C10	0.0329 (11)	0.0346 (11)	0.0277 (10)	0.0014 (9)	0.0071 (9)	0.0100 (8)
C11	0.0289 (10)	0.0245 (9)	0.0203 (9)	−0.0009 (8)	0.0019 (8)	0.0036 (7)
C12	0.0302 (11)	0.0368 (12)	0.0294 (11)	−0.0073 (9)	0.0045 (9)	−0.0034 (9)
C13	0.0499 (16)	0.0352 (13)	0.0436 (14)	−0.0134 (11)	0.0089 (12)	−0.0092 (10)
C14	0.0479 (15)	0.0363 (13)	0.0398 (13)	−0.0014 (11)	0.0066 (11)	−0.0106 (10)
C15	0.0369 (13)	0.0331 (12)	0.0353 (12)	0.0053 (9)	0.0057 (10)	−0.0009 (9)
C16	0.0304 (11)	0.0312 (11)	0.0286 (10)	0.0011 (8)	0.0068 (9)	0.0047 (8)

Geometric parameters (Å, º) top

I1—C4	2.097 (2)	C9—H9C	0.9800
I1—O2ⁱ	3.2688 (17)	C10—H10A	0.9800
S1—O2	1.4401 (17)	C10—H10B	0.9800
S1—O3	1.4403 (16)	C10—H10C	0.9800
S1—C1	1.742 (2)	C11—C16	1.522 (3)
S1—C11	1.790 (2)	C11—C12	1.530 (3)
O1—C8	1.365 (2)	C11—H11	1.0000
O1—C7	1.376 (2)	C12—C13	1.527 (3)
C1—C8	1.361 (3)	C12—H12A	0.9900
C1—C2	1.446 (3)	C12—H12B	0.9900
C2—C3	1.386 (3)	C13—C14	1.510 (4)
C2—C7	1.389 (3)	C13—H13A	0.9900
C3—C4	1.390 (3)	C13—H13B	0.9900
C3—H3	0.9500	C14—C15	1.528 (3)
C4—C5	1.398 (3)	C14—H14A	0.9900
C5—C6	1.380 (3)	C14—H14B	0.9900
C5—H5	0.9500	C15—C16	1.529 (3)
C6—C7	1.386 (3)	C15—H15A	0.9900
C6—C9	1.503 (3)	C15—H15B	0.9900
C8—C10	1.472 (3)	C16—H16A	0.9900
C9—H9A	0.9800	C16—H16B	0.9900
C9—H9B	0.9800

C4—I1—O2ⁱ	168.48 (6)	H10A—C10—H10B	109.5
O2—S1—O3	118.27 (10)	C8—C10—H10C	109.5
O2—S1—C1	107.00 (9)	H10A—C10—H10C	109.5
O3—S1—C1	109.53 (10)	H10B—C10—H10C	109.5
O2—S1—C11	107.41 (10)	C16—C11—C12	111.79 (17)
O3—S1—C11	109.40 (10)	C16—C11—S1	111.94 (14)
C1—S1—C11	104.32 (9)	C12—C11—S1	109.81 (15)
C8—O1—C7	107.13 (15)	C16—C11—H11	107.7
C8—C1—C2	107.46 (17)	C12—C11—H11	107.7
C8—C1—S1	127.49 (16)	S1—C11—H11	107.7
C2—C1—S1	124.98 (15)	C13—C12—C11	109.4 (2)
C3—C2—C7	119.59 (18)	C13—C12—H12A	109.8
C3—C2—C1	135.79 (18)	C11—C12—H12A	109.8
C7—C2—C1	104.61 (17)	C13—C12—H12B	109.8
C2—C3—C4	116.60 (18)	C11—C12—H12B	109.8
C2—C3—H3	121.7	H12A—C12—H12B	108.2
C4—C3—H3	121.7	C14—C13—C12	111.6 (2)
C3—C4—C5	122.42 (19)	C14—C13—H13A	109.3
C3—C4—I1	118.52 (14)	C12—C13—H13A	109.3
C5—C4—I1	119.05 (14)	C14—C13—H13B	109.3
C6—C5—C4	121.71 (18)	C12—C13—H13B	109.3
C6—C5—H5	119.1	H13A—C13—H13B	108.0
C4—C5—H5	119.1	C13—C14—C15	111.3 (2)
C5—C6—C7	114.71 (17)	C13—C14—H14A	109.4
C5—C6—C9	123.24 (19)	C15—C14—H14A	109.4
C7—C6—C9	122.03 (19)	C13—C14—H14B	109.4
O1—C7—C6	124.57 (17)	C15—C14—H14B	109.4
O1—C7—C2	110.47 (16)	H14A—C14—H14B	108.0
C6—C7—C2	124.95 (19)	C14—C15—C16	111.3 (2)
C1—C8—O1	110.33 (17)	C14—C15—H15A	109.4
C1—C8—C10	134.78 (19)	C16—C15—H15A	109.4
O1—C8—C10	114.89 (18)	C14—C15—H15B	109.4
C6—C9—H9A	109.5	C16—C15—H15B	109.4
C6—C9—H9B	109.5	H15A—C15—H15B	108.0
H9A—C9—H9B	109.5	C11—C16—C15	110.27 (19)
C6—C9—H9C	109.5	C11—C16—H16A	109.6
H9A—C9—H9C	109.5	C15—C16—H16A	109.6
H9B—C9—H9C	109.5	C11—C16—H16B	109.6
C8—C10—H10A	109.5	C15—C16—H16B	109.6
C8—C10—H10B	109.5	H16A—C16—H16B	108.1

O2—S1—C1—C8	−150.57 (18)	C9—C6—C7—C2	177.36 (18)
O3—S1—C1—C8	−21.2 (2)	C3—C2—C7—O1	179.81 (16)
C11—S1—C1—C8	95.78 (19)	C1—C2—C7—O1	0.2 (2)
O2—S1—C1—C2	32.94 (19)	C3—C2—C7—C6	1.2 (3)
O3—S1—C1—C2	162.28 (16)	C1—C2—C7—C6	−178.46 (18)
C11—S1—C1—C2	−80.70 (18)	C2—C1—C8—O1	−0.2 (2)
C8—C1—C2—C3	−179.5 (2)	S1—C1—C8—O1	−177.21 (14)
S1—C1—C2—C3	−2.4 (3)	C2—C1—C8—C10	179.9 (2)
C8—C1—C2—C7	0.0 (2)	S1—C1—C8—C10	2.9 (4)
S1—C1—C2—C7	177.11 (14)	C7—O1—C8—C1	0.3 (2)
C7—C2—C3—C4	−0.5 (3)	C7—O1—C8—C10	−179.77 (16)
C1—C2—C3—C4	179.0 (2)	O2—S1—C11—C16	172.45 (14)
C2—C3—C4—C5	0.0 (3)	O3—S1—C11—C16	42.91 (17)
C2—C3—C4—I1	−178.70 (13)	C1—S1—C11—C16	−74.20 (16)
O2ⁱ—I1—C4—C3	54.4 (4)	O2—S1—C11—C12	47.67 (17)
O2ⁱ—I1—C4—C5	−124.3 (3)	O3—S1—C11—C12	−81.87 (17)
C3—C4—C5—C6	0.0 (3)	C1—S1—C11—C12	161.02 (15)
I1—C4—C5—C6	178.69 (14)	C16—C11—C12—C13	57.2 (3)
C4—C5—C6—C7	0.5 (3)	S1—C11—C12—C13	−177.91 (17)
C4—C5—C6—C9	−177.95 (18)	C11—C12—C13—C14	−56.7 (3)
C8—O1—C7—C6	178.33 (18)	C12—C13—C14—C15	56.3 (3)
C8—O1—C7—C2	−0.3 (2)	C13—C14—C15—C16	−55.2 (3)
C5—C6—C7—O1	−179.56 (17)	C12—C11—C16—C15	−56.8 (2)
C9—C6—C7—O1	−1.1 (3)	S1—C11—C16—C15	179.57 (15)
C5—C6—C7—C2	−1.1 (3)	C14—C15—C16—C11	55.0 (3)

Symmetry code: (i) −x, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₆H₁₉IO₃S
M_r	418.27
Crystal system, space group	Triclinic, P1
Temperature (K)	173
a, b, c (Å)	6.8643 (2), 8.4981 (2), 14.2323 (3)
α, β, γ (°)	102.512 (1), 99.846 (1), 92.092 (1)
V (Å³)	796.23 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	2.15
Crystal size (mm)	0.24 × 0.16 × 0.14

Data collection
Diffractometer	Bruker SMART APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.629, 0.759
No. of measured, independent and observed [I > 2σ(I)] reflections	15021, 3997, 3753
R_int	0.035
(sin θ/λ)_max (Å⁻¹)	0.670

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.023, 0.058, 1.06
No. of reflections	3997
No. of parameters	192
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.68, −0.63

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 1998).

References

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