5-Chloro-3-ethyl­sulfinyl-7-methyl-2-(4-methyl­phen­yl)-1-benzo­furan

Choi, H.D.; Seo, P.J.; Lee, U.

doi:10.1107/S1600536814005601

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 70| Part 4| April 2014| Page o458

doi:10.1107/S1600536814005601

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5-Chloro-3-ethylsulfinyl-7-methyl-2-(4-methylphenyl)-1-benzofuran

Hong Dae Choi,^a Pil Ja Seo ^a 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 4 February 2014; accepted 11 March 2014; online 19 March 2014)

In the title compound, C₁₈H₁₇ClO₂S, the dihedral angle between the mean planes of the benzofuran ring system and the methylphenyl ring is 14.50 (4)°. The centroid–centroid distances between the benzene and the methylphenyl rings are 3.827 (2) and 3.741 (2) Å, while the centroid–centroid distance between the furan and methylphenyl rings is 3.843 (2) Å. These distances indicate π–π interactions; on the other hand, the interplanar angles between the benzene and methylphenyl rings, and between the furan and methylphenyl rings are 13.89 (4) and 15.53 (4)°, respectively. In the crystal, the molecules stack along the a-axis direction.

CCDC reference: 991267

Related literature

For background information about related compounds and their crystal structures, see Choi et al. (2010a ,b ). For π–π stacking in metal complexes with aromatic nitrogen ligands, see: Janiak (2000 ).

Experimental

Crystal data

C₁₈H₁₇ClO₂S
M_r = 332.83
Triclinic, $[P \overline 1]$
a = 7.3638 (5) Å
b = 10.2524 (6) Å
c = 11.8335 (7) Å
α = 68.949 (3)°
β = 89.362 (3)°
γ = 71.460 (3)°
V = 785.11 (8) Å³
Z = 2
Mo Kα radiation
μ = 0.38 mm⁻¹
T = 173 K
0.46 × 0.37 × 0.33 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.691, T_max = 0.746
13937 measured reflections
3759 independent reflections
3348 reflections with I > 2σ(I)
R_int = 0.031

Refinement

R[F² > 2σ(F²)] = 0.034
wR(F²) = 0.100
S = 1.06
3759 reflections
203 parameters
H-atom parameters constrained
Δρ_max = 0.31 e Å⁻³
Δρ_min = −0.29 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 for Windows (Farrugia, 2012 ) and DIAMOND (Brandenburg, 1998 ); software used to prepare material for publication: SHELXL97.

Supporting information

CCDC reference: 991267

Crystal structure: contains datablock I. DOI: 10.1107/S1600536814005601/fb2296sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536814005601/fb2296Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536814005601/fb2296Isup3.cml

checkCIF report

Comment top

As a part of our ongoing study of 5-chloro-3-ethylsulfinyl-7-methyl-1-benzofuran derivatives which contain 4-fluorophenyl and 4 iodophenyl substituents in the 2-position (Choi et al. (2010a,b) for the F and I-compound, respectively), we report the crystal structure of the title compound.

In the title molecule (Fig. 1), the benzofuran unit is essentially planar, with the mean deviation from the least-squares plane defined by the nine constituent atoms which equals to 0.016 (1) Å. The 4-methylphenyl ring is also essentially planar, with the mean deviation of 0.004 (1) Å from the least-squares plane defined by the six core-ring atoms. The dihedral angle between the benzofuran ring system and the core of the 4-methylphenyl rings is 14.50 (4)°.

Let the centroid names Cg1, Cg2 and Cg3 be assigned to the benzene ring (C2–C7), the furan ring (C1/C2/C7/O1/C8) and the core of 4-methylphenyl ring (C10–C15), respectively: The centroid–centroid separations of Cg1···Cg3ⁱ, Cg1···Cg3ⁱⁱ and Cg2···Cg3ⁱ are 3.827 (2), 3.741 (2) and 3.843 (2) Å, respectively. (The symmetry codes are: (i) -x + 1, -y + 1, -z + 1; (ii) -x, -y + 1, -z + 1.)

The interplanar angles between the benzene and the core of 4-methylphenyl ring and between the furan and the core of 4-methylphenyl ring equal to 13.89 (4) and 15.53 (4)°, respectively. These angles are quite large for the rings being in π-electron···π-electron interactions as it follows from the study by Janiak (2000) who investigated π–π stacking in metal complexes with aromatic nitrogen ligands. According to Fig. 8 of Janiak's study, the interplanar angles between the rings that are involved in π-electron···π-electron interactions are less than 10° in overwhelming majority of cases.

Related literature top

For the background information about related compounds and their crystal structures, see Choi et al. (2010a,b). For π–π stacking in metal complexes with aromatic nitrogen ligands, see: Janiak (2000).

Experimental top

3-Chloroperoxybenzoic acid (77%, 224 mg, 1.0 mmol) was added in small portions to the stirred solution of 5-chloro-3-ethylsulfanyl-7-methyl-2-(4-methylphenyl)-1-benzofuran (285 mg, 0.9 mmol) in dichloromethane (30 ml) at 273 K. The mixture was washed with saturated sodium hydrogen carbonate solution after having been stirred at room temperature for 4h. 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, 1:1v/v) to afford the title compound as a colourless solid [yield 71%, m.p. 392–393 K; R_f = 0.56 (hexane–ethyl acetate, 1:1 v/v)]. Single crystals suitable for X-ray diffraction were prepared by slow evaporation of the 5% solution of the title compound in acetone at room temperature. The average crystal size was approximately 1.1 × 1.3 × 0.8 mm. (The measured crystal was cut from a large one.) The crystals are soluble in polar solvents.

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 for Windows (Farrugia, 2012) and DIAMOND (Brandenburg, 1998); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The title molecule with the atom numbering scheme. The displacement ellipsoids are drawn at the 50% probability level. The hydrogen atoms are presented as small spheres of arbitrary radius.
	Fig. 2. A view of possible π···π interactions (dotted lines) in the crystal structure of the title compound. The H-atoms have been omitted for clarity. [Symmetry codes: (i) -x + 1, -y + 1, -z + 1; (ii) -x, -y + 1, -z + 1.]

5-Chloro-3-ethylsulfinyl-7-methyl-2-(4-methylphenyl)-1-benzofuran top

Crystal data top

C₁₈H₁₇ClO₂S	Z = 2
M_r = 332.83	F(000) = 348
Triclinic, P1	D_x = 1.408 Mg m⁻³
Hall symbol: -P 1	Melting point = 392–393 K
a = 7.3638 (5) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.2524 (6) Å	Cell parameters from 8286 reflections
c = 11.8335 (7) Å	θ = 2.3–28.4°
α = 68.949 (3)°	µ = 0.38 mm⁻¹
β = 89.362 (3)°	T = 173 K
γ = 71.460 (3)°	Block, colourless
V = 785.11 (8) Å³	0.46 × 0.37 × 0.33 mm

Data collection top

Bruker SMART APEXII CCD diffractometer	3759 independent reflections
Radiation source: rotating anode	3348 reflections with I > 2σ(I)
Graphite multilayer monochromator	R_int = 0.031
Detector resolution: 10.0 pixels mm^-1	θ_max = 28.0°, θ_min = 2.3°
ϕ and ω scans	h = −9→9
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −13→13
T_min = 0.691, T_max = 0.746	l = −15→15
13937 measured reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F² > 2σ(F²)] = 0.034	H-atom parameters constrained
wR(F²) = 0.100	w = 1/[σ²(F_o²) + (0.0517P)² + 0.2412P] where P = (F_o² + 2F_c²)/3
S = 1.06	(Δ/σ)_max < 0.001
3759 reflections	Δρ_max = 0.31 e Å⁻³
203 parameters	Δρ_min = −0.29 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.006 (2)

Crystal data top

C₁₈H₁₇ClO₂S	γ = 71.460 (3)°
M_r = 332.83	V = 785.11 (8) Å³
Triclinic, P1	Z = 2
a = 7.3638 (5) Å	Mo Kα radiation
b = 10.2524 (6) Å	µ = 0.38 mm⁻¹
c = 11.8335 (7) Å	T = 173 K
α = 68.949 (3)°	0.46 × 0.37 × 0.33 mm
β = 89.362 (3)°

Data collection top

Bruker SMART APEXII CCD diffractometer	3759 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	3348 reflections with I > 2σ(I)
T_min = 0.691, T_max = 0.746	R_int = 0.031
13937 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.034	0 restraints
wR(F²) = 0.100	H-atom parameters constrained
S = 1.06	Δρ_max = 0.31 e Å⁻³
3759 reflections	Δρ_min = −0.29 e Å⁻³
203 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	0.02297 (6)	0.70926 (4)	−0.07104 (3)	0.03932 (13)
S1	0.36271 (5)	0.19161 (4)	0.40911 (3)	0.02784 (11)
O1	0.19351 (14)	0.58273 (10)	0.44275 (8)	0.0265 (2)
O2	0.21419 (17)	0.18248 (12)	0.32973 (11)	0.0411 (3)
C1	0.29375 (19)	0.37881 (14)	0.39556 (12)	0.0251 (3)
C2	0.20899 (19)	0.50599 (14)	0.28375 (12)	0.0248 (3)
C3	0.1735 (2)	0.52797 (15)	0.16126 (13)	0.0279 (3)
H3	0.2128	0.4481	0.1335	0.033*
C4	0.0781 (2)	0.67216 (16)	0.08294 (13)	0.0290 (3)
C5	0.0153 (2)	0.79189 (15)	0.12135 (13)	0.0298 (3)
H5	−0.0515	0.8884	0.0634	0.036*
C7	0.14795 (19)	0.62695 (15)	0.31933 (12)	0.0251 (3)
C6	0.0489 (2)	0.77201 (15)	0.24256 (13)	0.0273 (3)
C8	0.28210 (19)	0.43087 (14)	0.48790 (12)	0.0249 (3)
C9	−0.0186 (2)	0.89610 (16)	0.28858 (15)	0.0343 (3)
H9A	−0.1057	0.9849	0.2243	0.052*
H9B	0.0929	0.9177	0.3116	0.052*
H9C	−0.0870	0.8668	0.3599	0.052*
C10	0.3426 (2)	0.36521 (15)	0.61893 (12)	0.0262 (3)
C11	0.2685 (2)	0.44896 (16)	0.69082 (13)	0.0299 (3)
H11	0.1763	0.5457	0.6543	0.036*
C12	0.3291 (2)	0.39130 (18)	0.81450 (14)	0.0343 (3)
H12	0.2787	0.4499	0.8615	0.041*
C13	0.4619 (2)	0.24959 (18)	0.87129 (13)	0.0339 (3)
C14	0.5333 (2)	0.16600 (17)	0.80041 (14)	0.0338 (3)
H14	0.6229	0.0683	0.8379	0.041*
C15	0.4761 (2)	0.22262 (16)	0.67607 (13)	0.0297 (3)
H15	0.5282	0.1639	0.6294	0.036*
C16	0.5257 (3)	0.1898 (2)	1.00639 (14)	0.0458 (4)
H16A	0.6069	0.0852	1.0331	0.069*
H16B	0.4121	0.1986	1.0509	0.069*
H16C	0.5994	0.2468	1.0229	0.069*
C17	0.5744 (2)	0.18473 (17)	0.32871 (14)	0.0336 (3)
H17A	0.6062	0.1004	0.3012	0.040*
H17B	0.5467	0.2772	0.2556	0.040*
C18	0.7460 (2)	0.16692 (17)	0.40993 (15)	0.0363 (3)
H18A	0.7127	0.2480	0.4401	0.054*
H18B	0.8561	0.1696	0.3630	0.054*
H18C	0.7798	0.0717	0.4791	0.054*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0511 (3)	0.0362 (2)	0.02820 (19)	−0.01466 (18)	−0.00402 (16)	−0.00909 (15)
S1	0.0307 (2)	0.02136 (17)	0.03107 (19)	−0.00773 (14)	0.00090 (14)	−0.01020 (13)
O1	0.0277 (5)	0.0223 (5)	0.0278 (5)	−0.0054 (4)	0.0023 (4)	−0.0101 (4)
O2	0.0422 (7)	0.0359 (6)	0.0484 (7)	−0.0158 (5)	−0.0071 (5)	−0.0166 (5)
C1	0.0235 (6)	0.0218 (6)	0.0280 (6)	−0.0057 (5)	0.0031 (5)	−0.0089 (5)
C2	0.0210 (6)	0.0230 (6)	0.0296 (7)	−0.0065 (5)	0.0029 (5)	−0.0098 (5)
C3	0.0274 (7)	0.0263 (6)	0.0304 (7)	−0.0080 (5)	0.0016 (5)	−0.0119 (5)
C4	0.0283 (7)	0.0304 (7)	0.0275 (7)	−0.0106 (6)	−0.0006 (5)	−0.0092 (5)
C5	0.0274 (7)	0.0240 (6)	0.0334 (7)	−0.0067 (5)	−0.0010 (6)	−0.0070 (5)
C7	0.0225 (6)	0.0241 (6)	0.0280 (6)	−0.0068 (5)	0.0017 (5)	−0.0100 (5)
C6	0.0226 (6)	0.0236 (6)	0.0338 (7)	−0.0059 (5)	0.0019 (5)	−0.0103 (5)
C8	0.0222 (6)	0.0216 (6)	0.0304 (7)	−0.0068 (5)	0.0041 (5)	−0.0098 (5)
C9	0.0339 (8)	0.0237 (7)	0.0410 (8)	−0.0028 (6)	0.0020 (6)	−0.0130 (6)
C10	0.0258 (7)	0.0275 (6)	0.0275 (6)	−0.0121 (5)	0.0056 (5)	−0.0102 (5)
C11	0.0320 (7)	0.0292 (7)	0.0318 (7)	−0.0132 (6)	0.0080 (6)	−0.0129 (6)
C12	0.0398 (8)	0.0396 (8)	0.0318 (7)	−0.0199 (7)	0.0115 (6)	−0.0173 (6)
C13	0.0327 (8)	0.0441 (8)	0.0278 (7)	−0.0205 (7)	0.0064 (6)	−0.0104 (6)
C14	0.0294 (7)	0.0340 (7)	0.0315 (7)	−0.0097 (6)	0.0021 (6)	−0.0058 (6)
C15	0.0270 (7)	0.0313 (7)	0.0304 (7)	−0.0088 (6)	0.0042 (5)	−0.0121 (6)
C16	0.0473 (10)	0.0616 (11)	0.0283 (8)	−0.0238 (9)	0.0054 (7)	−0.0117 (7)
C17	0.0341 (8)	0.0309 (7)	0.0331 (7)	−0.0029 (6)	0.0056 (6)	−0.0160 (6)
C18	0.0332 (8)	0.0325 (7)	0.0451 (9)	−0.0107 (6)	0.0082 (6)	−0.0172 (7)

Geometric parameters (Å, º) top

Cl1—C4	1.7465 (15)	C10—C15	1.397 (2)
S1—O2	1.4962 (12)	C10—C11	1.4054 (19)
S1—C1	1.7686 (13)	C11—C12	1.384 (2)
S1—C17	1.8129 (16)	C11—H11	0.9500
O1—C7	1.3746 (16)	C12—C13	1.389 (2)
O1—C8	1.3782 (15)	C12—H12	0.9500
C1—C8	1.3689 (19)	C13—C14	1.391 (2)
C1—C2	1.4498 (18)	C13—C16	1.510 (2)
C2—C7	1.3905 (18)	C14—C15	1.387 (2)
C2—C3	1.3988 (19)	C14—H14	0.9500
C3—C4	1.3811 (19)	C15—H15	0.9500
C3—H3	0.9500	C16—H16A	0.9800
C4—C5	1.401 (2)	C16—H16B	0.9800
C5—C6	1.388 (2)	C16—H16C	0.9800
C5—H5	0.9500	C17—C18	1.519 (2)
C7—C6	1.3868 (18)	C17—H17A	0.9900
C6—C9	1.5006 (19)	C17—H17B	0.9900
C8—C10	1.4597 (19)	C18—H18A	0.9800
C9—H9A	0.9800	C18—H18B	0.9800
C9—H9B	0.9800	C18—H18C	0.9800
C9—H9C	0.9800

O2—S1—C1	106.72 (6)	C15—C10—C8	122.50 (13)
O2—S1—C17	106.62 (7)	C11—C10—C8	119.29 (12)
C1—S1—C17	98.27 (7)	C12—C11—C10	120.40 (14)
C7—O1—C8	107.00 (10)	C12—C11—H11	119.8
C8—C1—C2	107.17 (12)	C10—C11—H11	119.8
C8—C1—S1	127.41 (10)	C11—C12—C13	121.40 (14)
C2—C1—S1	124.75 (10)	C11—C12—H12	119.3
C7—C2—C3	119.38 (12)	C13—C12—H12	119.3
C7—C2—C1	104.93 (12)	C12—C13—C14	118.17 (14)
C3—C2—C1	135.63 (13)	C12—C13—C16	120.22 (15)
C4—C3—C2	116.30 (13)	C14—C13—C16	121.61 (15)
C4—C3—H3	121.8	C15—C14—C13	121.24 (14)
C2—C3—H3	121.8	C15—C14—H14	119.4
C3—C4—C5	123.25 (13)	C13—C14—H14	119.4
C3—C4—Cl1	119.41 (11)	C14—C15—C10	120.58 (14)
C5—C4—Cl1	117.29 (11)	C14—C15—H15	119.7
C6—C5—C4	121.19 (13)	C10—C15—H15	119.7
C6—C5—H5	119.4	C13—C16—H16A	109.5
C4—C5—H5	119.4	C13—C16—H16B	109.5
O1—C7—C6	124.11 (12)	H16A—C16—H16B	109.5
O1—C7—C2	110.69 (11)	C13—C16—H16C	109.5
C6—C7—C2	125.17 (13)	H16A—C16—H16C	109.5
C7—C6—C5	114.68 (12)	H16B—C16—H16C	109.5
C7—C6—C9	122.11 (13)	C18—C17—S1	111.08 (10)
C5—C6—C9	123.20 (13)	C18—C17—H17A	109.4
C1—C8—O1	110.19 (12)	S1—C17—H17A	109.4
C1—C8—C10	135.60 (12)	C18—C17—H17B	109.4
O1—C8—C10	114.20 (11)	S1—C17—H17B	109.4
C6—C9—H9A	109.5	H17A—C17—H17B	108.0
C6—C9—H9B	109.5	C17—C18—H18A	109.5
H9A—C9—H9B	109.5	C17—C18—H18B	109.5
C6—C9—H9C	109.5	H18A—C18—H18B	109.5
H9A—C9—H9C	109.5	C17—C18—H18C	109.5
H9B—C9—H9C	109.5	H18A—C18—H18C	109.5
C15—C10—C11	118.19 (13)	H18B—C18—H18C	109.5

O2—S1—C1—C8	131.72 (13)	C4—C5—C6—C7	0.2 (2)
C17—S1—C1—C8	−118.07 (13)	C4—C5—C6—C9	−178.83 (14)
O2—S1—C1—C2	−37.66 (13)	C2—C1—C8—O1	0.68 (15)
C17—S1—C1—C2	72.54 (13)	S1—C1—C8—O1	−170.20 (10)
C8—C1—C2—C7	−1.27 (15)	C2—C1—C8—C10	−178.15 (15)
S1—C1—C2—C7	169.92 (10)	S1—C1—C8—C10	11.0 (2)
C8—C1—C2—C3	−178.44 (15)	C7—O1—C8—C1	0.20 (14)
S1—C1—C2—C3	−7.3 (2)	C7—O1—C8—C10	179.30 (11)
C7—C2—C3—C4	0.1 (2)	C1—C8—C10—C15	15.7 (2)
C1—C2—C3—C4	176.96 (15)	O1—C8—C10—C15	−163.06 (12)
C2—C3—C4—C5	−1.2 (2)	C1—C8—C10—C11	−165.94 (15)
C2—C3—C4—Cl1	−178.57 (10)	O1—C8—C10—C11	15.27 (18)
C3—C4—C5—C6	1.0 (2)	C15—C10—C11—C12	0.8 (2)
Cl1—C4—C5—C6	178.51 (11)	C8—C10—C11—C12	−177.59 (13)
C8—O1—C7—C6	176.97 (13)	C10—C11—C12—C13	−0.8 (2)
C8—O1—C7—C2	−1.06 (14)	C11—C12—C13—C14	0.0 (2)
C3—C2—C7—O1	179.17 (11)	C11—C12—C13—C16	179.84 (14)
C1—C2—C7—O1	1.44 (15)	C12—C13—C14—C15	0.9 (2)
C3—C2—C7—C6	1.2 (2)	C16—C13—C14—C15	−179.02 (14)
C1—C2—C7—C6	−176.57 (13)	C13—C14—C15—C10	−0.8 (2)
O1—C7—C6—C5	−179.01 (12)	C11—C10—C15—C14	0.0 (2)
C2—C7—C6—C5	−1.3 (2)	C8—C10—C15—C14	178.34 (13)
O1—C7—C6—C9	0.0 (2)	O2—S1—C17—C18	−170.38 (10)
C2—C7—C6—C9	177.75 (13)	C1—S1—C17—C18	79.34 (11)

Experimental details

Crystal data
Chemical formula	C₁₈H₁₇ClO₂S
M_r	332.83
Crystal system, space group	Triclinic, P1
Temperature (K)	173
a, b, c (Å)	7.3638 (5), 10.2524 (6), 11.8335 (7)
α, β, γ (°)	68.949 (3), 89.362 (3), 71.460 (3)
V (Å³)	785.11 (8)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.38
Crystal size (mm)	0.46 × 0.37 × 0.33

Data collection
Diffractometer	Bruker SMART APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.691, 0.746
No. of measured, independent and observed [I > 2σ(I)] reflections	13937, 3759, 3348
R_int	0.031
(sin θ/λ)_max (Å⁻¹)	0.661

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.034, 0.100, 1.06
No. of reflections	3759
No. of parameters	203
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.31, −0.29

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 2012) and DIAMOND (Brandenburg, 1998).

References

Brandenburg, K. (1998). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Bruker (2009). APEX2, SADABS and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2010a). Acta Cryst. E66, o886. Web of Science CrossRef IUCr Journals Google Scholar
Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2010b). Acta Cryst. E66, o2277. Web of Science CSD CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854. Web of Science CrossRef CAS IUCr Journals Google Scholar
Janiak, C. (2000). J. Chem. Soc. Dalton Trans. pp. 3885–3896. Web of Science CrossRef Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar