2-(3-Fluoro­phen­yl)-3-methyl­sulfanyl-5-phenyl-1-benzofuran

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

doi:10.1107/S1600536811042541

organic compounds

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ISSN: 2056-9890

Volume 67| Part 11| November 2011| Page o3006

doi:10.1107/S1600536811042541

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2-(3-Fluorophenyl)-3-methylsulfanyl-5-phenyl-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 10 October 2011; accepted 14 October 2011; online 22 October 2011)

In the title compound, C₂₁H₁₅FOS, the dihedral angles between the mean plane of the benzofuran fragment and the pendant 3-fluorophenyl and phenyl rings are 1.76 (5) and 32.29 (5)°, respectively. In the crystal, molecules are linked by a slipped π–π interaction between the furan and benzene rings of neighbouring molecules [centroid–centroid distance = 3.665 (2) Å, interplanar distance = 3.391 (2) Å and slippage = 1.390 (2) 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 related structures, see: Choi et al. (2009 , 2010 ).

Experimental

Crystal data

C₂₁H₁₅FOS
M_r = 334.39
Triclinic, $[P \overline 1]$
a = 4.7692 (1) Å
b = 9.6442 (2) Å
c = 17.4049 (3) Å
α = 89.7700 (1)°
β = 87.589 (1)°
γ = 80.061 (1)°
V = 787.82 (3) Å³
Z = 2
Mo Kα radiation
μ = 0.22 mm⁻¹
T = 296 K
0.34 × 0.25 × 0.12 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.929, T_max = 0.974
13895 measured reflections
3590 independent reflections
3234 reflections with I > 2σ(I)
R_int = 0.023

Refinement

R[F² > 2σ(F²)] = 0.034
wR(F²) = 0.091
S = 1.04
3590 reflections
218 parameters
H-atom parameters constrained
Δρ_max = 0.30 e Å⁻³
Δρ_min = −0.25 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/S1600536811042541/ff2033sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811042541/ff2033Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811042541/ff2033Isup3.cml

checkCIF report

Comment top

Recently, many compounds having a benzofuran moiety have drawn much attention due 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 benzofuranderivatives containing either 2-(4-fluorophenyl) (Choi et al., 2009) or 2-(4-chlorophenyl) (Choi et al., 2010) substituents, 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 (1) Å from the least-squares plane defined by the nine constituent atoms. The dihedral angles between the mean plane of the benzofuran fragment and the 4-fluorophenyl and phenyl rings are 1.76 (5)° and 32.29 (5)°, respectively. The crystal packing (Fig. 2) is stabilized by a slipped π–π interaction between the furan and benzene rings of adjacent molecules, with a Cg1···Cg2ⁱ distance of 3.665 (2) Å and an interplanar distance of 3.391 (2) Å resulting in a slippage of 1.390 (2) Å (Cg1 and Cg2 are the centroids of the C1/C2/C7/O1/C8 furan ring and the C2–C7 benzene ring, respectively).

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 related structures, see: Choi et al. (2009, 2010).

Experimental top

Zinc chloride (273 mg, 2.0 mmol) was added to a stirred solution of 4-phenylphenol (340 mg, 2.0 mmol) and 2-chloro-2-methylsulfanyl-3'-fluoroacetophenone (437 mg, 2.0 mmol) in dichloromethane (30 mL) at room temperature, and stirring was continued at the same temperature for 1h. The reaction was quenched by the addition of water and the organic layer was separated, dried over magnesium sulfate, filtered and concentrated at reduced pressure. The residue was purified by column chromatography (hexane–benzene, 5:2 v/v) to afford the title compound as a colorless solid [yield 54%, m.p. 357–358 K; R_f = 0.61 (hexane–benzene, 5:2 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 small spheres of arbitrary radius.
	Fig. 2. A view of the π–π interactions (dotted lines) in the crystal structure of the title compound. H atoms were omitted for clarity. [Symmetry codes: (i) x - 1, y, z; (ii) x + 1, y, z.]

2-(3-Fluorophenyl)-3-methylsulfanyl-5-phenyl-1-benzofuran top

Crystal data top

C₂₁H₁₅FOS	Z = 2
M_r = 334.39	F(000) = 348
Triclinic, P1	D_x = 1.410 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 4.7692 (1) Å	Cell parameters from 7407 reflections
b = 9.6442 (2) Å	θ = 2.3–27.5°
c = 17.4049 (3) Å	µ = 0.22 mm⁻¹
α = 89.7700 (1)°	T = 296 K
β = 87.589 (1)°	Block, colourless
γ = 80.061 (1)°	0.34 × 0.25 × 0.12 mm
V = 787.82 (3) Å³

Data collection top

Bruker SMART APEXII CCD diffractometer	3590 independent reflections
Radiation source: rotating anode	3234 reflections with I > 2σ(I)
Graphite multilayer monochromator	R_int = 0.023
Detector resolution: 10.0 pixels mm^-1	θ_max = 27.5°, θ_min = 2.1°
ϕ and ω scans	h = −6→6
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −12→12
T_min = 0.929, T_max = 0.974	l = −22→22
13895 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)] = 0.034	Hydrogen site location: difference Fourier map
wR(F²) = 0.091	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0451P)² + 0.3462P] where P = (F_o² + 2F_c²)/3
3590 reflections	(Δ/σ)_max < 0.001
218 parameters	Δρ_max = 0.30 e Å⁻³
0 restraints	Δρ_min = −0.25 e Å⁻³

Crystal data top

C₂₁H₁₅FOS	γ = 80.061 (1)°
M_r = 334.39	V = 787.82 (3) Å³
Triclinic, P1	Z = 2
a = 4.7692 (1) Å	Mo Kα radiation
b = 9.6442 (2) Å	µ = 0.22 mm⁻¹
c = 17.4049 (3) Å	T = 296 K
α = 89.7700 (1)°	0.34 × 0.25 × 0.12 mm
β = 87.589 (1)°

Data collection top

Bruker SMART APEXII CCD diffractometer	3590 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	3234 reflections with I > 2σ(I)
T_min = 0.929, T_max = 0.974	R_int = 0.023
13895 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.034	0 restraints
wR(F²) = 0.091	H-atom parameters constrained
S = 1.04	Δρ_max = 0.30 e Å⁻³
3590 reflections	Δρ_min = −0.25 e Å⁻³
218 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
S1	0.94952 (7)	0.43069 (3)	0.147672 (18)	0.02311 (10)
F1	0.2102 (2)	0.79398 (10)	0.01953 (5)	0.0391 (2)
O1	1.05781 (19)	0.76869 (9)	0.26561 (5)	0.0218 (2)
C1	1.0423 (3)	0.56199 (13)	0.20611 (7)	0.0196 (2)
C2	1.2552 (3)	0.53713 (13)	0.26345 (7)	0.0199 (2)
C3	1.4383 (3)	0.41893 (13)	0.28916 (7)	0.0198 (2)
H3	1.4391	0.3310	0.2674	0.024*
C4	1.6195 (3)	0.43454 (13)	0.34781 (7)	0.0200 (2)
C5	1.6144 (3)	0.56915 (14)	0.38003 (7)	0.0232 (3)
H5	1.7378	0.5787	0.4189	0.028*
C6	1.4325 (3)	0.68749 (14)	0.35590 (7)	0.0238 (3)
H6	1.4295	0.7757	0.3777	0.029*
C7	1.2556 (3)	0.66699 (13)	0.29759 (7)	0.0205 (2)
C8	0.9298 (3)	0.70255 (13)	0.20980 (7)	0.0203 (2)
C9	1.8215 (3)	0.31190 (13)	0.37610 (7)	0.0211 (3)
C10	1.9415 (3)	0.20260 (14)	0.32642 (8)	0.0248 (3)
H10	1.8910	0.2055	0.2753	0.030*
C11	2.1353 (3)	0.08960 (14)	0.35218 (8)	0.0308 (3)
H11	2.2143	0.0176	0.3184	0.037*
C12	2.2111 (4)	0.08401 (15)	0.42809 (9)	0.0367 (4)
H12	2.3420	0.0087	0.4453	0.044*
C13	2.0914 (4)	0.19081 (16)	0.47824 (9)	0.0362 (4)
H13	2.1406	0.1867	0.5294	0.043*
C14	1.8985 (3)	0.30393 (15)	0.45263 (8)	0.0279 (3)
H14	1.8195	0.3753	0.4868	0.034*
C15	0.7126 (3)	0.79758 (13)	0.16924 (7)	0.0212 (3)
C16	0.6597 (3)	0.94127 (15)	0.18697 (8)	0.0299 (3)
H16	0.7610	0.9756	0.2250	0.036*
C17	0.4572 (3)	1.03289 (16)	0.14822 (9)	0.0357 (3)
H17	0.4239	1.1281	0.1608	0.043*
C18	0.3041 (3)	0.98512 (16)	0.09120 (8)	0.0315 (3)
H18	0.1692	1.0464	0.0648	0.038*
C19	0.3592 (3)	0.84369 (15)	0.07508 (8)	0.0262 (3)
C20	0.5568 (3)	0.74876 (14)	0.11223 (7)	0.0237 (3)
H20	0.5859	0.6536	0.0995	0.028*
C21	1.2261 (3)	0.41386 (17)	0.07312 (9)	0.0352 (3)
H21A	1.2159	0.5014	0.0461	0.053*
H21B	1.2017	0.3410	0.0379	0.053*
H21C	1.4086	0.3902	0.0956	0.053*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.02386 (17)	0.02130 (17)	0.02495 (17)	−0.00512 (12)	−0.00487 (12)	−0.00323 (12)
F1	0.0392 (5)	0.0395 (5)	0.0387 (5)	−0.0029 (4)	−0.0205 (4)	−0.0007 (4)
O1	0.0230 (5)	0.0190 (4)	0.0229 (4)	−0.0008 (3)	−0.0057 (3)	−0.0021 (3)
C1	0.0188 (6)	0.0206 (6)	0.0196 (6)	−0.0038 (4)	−0.0018 (4)	−0.0009 (4)
C2	0.0189 (6)	0.0217 (6)	0.0194 (6)	−0.0048 (5)	−0.0001 (4)	−0.0014 (5)
C3	0.0204 (6)	0.0181 (6)	0.0212 (6)	−0.0042 (4)	−0.0001 (4)	−0.0014 (4)
C4	0.0204 (6)	0.0192 (6)	0.0204 (6)	−0.0033 (5)	−0.0001 (4)	0.0004 (4)
C5	0.0248 (6)	0.0236 (6)	0.0214 (6)	−0.0035 (5)	−0.0054 (5)	−0.0022 (5)
C6	0.0278 (7)	0.0193 (6)	0.0243 (6)	−0.0029 (5)	−0.0040 (5)	−0.0048 (5)
C7	0.0204 (6)	0.0186 (6)	0.0217 (6)	−0.0009 (4)	−0.0021 (5)	0.0003 (5)
C8	0.0204 (6)	0.0222 (6)	0.0189 (6)	−0.0051 (5)	−0.0018 (4)	−0.0016 (5)
C9	0.0208 (6)	0.0198 (6)	0.0235 (6)	−0.0053 (5)	−0.0033 (5)	0.0022 (5)
C10	0.0297 (7)	0.0203 (6)	0.0245 (6)	−0.0038 (5)	−0.0056 (5)	0.0008 (5)
C11	0.0365 (8)	0.0198 (6)	0.0342 (8)	0.0015 (5)	−0.0069 (6)	−0.0032 (5)
C12	0.0435 (9)	0.0221 (7)	0.0427 (9)	0.0034 (6)	−0.0199 (7)	0.0010 (6)
C13	0.0486 (9)	0.0287 (7)	0.0307 (7)	−0.0009 (6)	−0.0183 (7)	0.0010 (6)
C14	0.0344 (7)	0.0241 (7)	0.0245 (7)	−0.0015 (5)	−0.0061 (5)	−0.0022 (5)
C15	0.0189 (6)	0.0223 (6)	0.0219 (6)	−0.0024 (5)	0.0002 (5)	0.0012 (5)
C16	0.0318 (7)	0.0243 (7)	0.0328 (7)	−0.0010 (5)	−0.0093 (6)	−0.0027 (5)
C17	0.0408 (8)	0.0227 (7)	0.0413 (8)	0.0030 (6)	−0.0113 (7)	−0.0011 (6)
C18	0.0284 (7)	0.0310 (7)	0.0327 (7)	0.0030 (6)	−0.0067 (6)	0.0060 (6)
C19	0.0229 (6)	0.0330 (7)	0.0233 (6)	−0.0054 (5)	−0.0049 (5)	0.0007 (5)
C20	0.0235 (6)	0.0235 (6)	0.0240 (6)	−0.0031 (5)	−0.0023 (5)	0.0000 (5)
C21	0.0333 (8)	0.0419 (9)	0.0319 (7)	−0.0110 (6)	0.0015 (6)	−0.0137 (6)

Geometric parameters (Å, º) top

S1—C1	1.7537 (13)	C10—H10	0.9300
S1—C21	1.7984 (15)	C11—C12	1.383 (2)
F1—C19	1.3597 (16)	C11—H11	0.9300
O1—C7	1.3719 (14)	C12—C13	1.382 (2)
O1—C8	1.3830 (15)	C12—H12	0.9300
C1—C8	1.3698 (17)	C13—C14	1.3854 (19)
C1—C2	1.4435 (17)	C13—H13	0.9300
C2—C7	1.3887 (17)	C14—H14	0.9300
C2—C3	1.3955 (17)	C15—C20	1.3946 (18)
C3—C4	1.3897 (17)	C15—C16	1.3984 (19)
C3—H3	0.9300	C16—C17	1.387 (2)
C4—C5	1.4122 (18)	C16—H16	0.9300
C4—C9	1.4873 (17)	C17—C18	1.383 (2)
C5—C6	1.3843 (18)	C17—H17	0.9300
C5—H5	0.9300	C18—C19	1.372 (2)
C6—C7	1.3829 (18)	C18—H18	0.9300
C6—H6	0.9300	C19—C20	1.3758 (18)
C8—C15	1.4629 (17)	C20—H20	0.9300
C9—C10	1.3942 (18)	C21—H21A	0.9600
C9—C14	1.3948 (18)	C21—H21B	0.9600
C10—C11	1.3879 (18)	C21—H21C	0.9600

C1—S1—C21	101.72 (6)	C10—C11—H11	120.0
C7—O1—C8	106.60 (9)	C13—C12—C11	119.73 (13)
C8—C1—C2	106.46 (11)	C13—C12—H12	120.1
C8—C1—S1	129.09 (10)	C11—C12—H12	120.1
C2—C1—S1	124.41 (9)	C12—C13—C14	120.36 (13)
C7—C2—C3	119.37 (11)	C12—C13—H13	119.8
C7—C2—C1	105.75 (11)	C14—C13—H13	119.8
C3—C2—C1	134.88 (12)	C13—C14—C9	120.69 (13)
C4—C3—C2	119.05 (11)	C13—C14—H14	119.7
C4—C3—H3	120.5	C9—C14—H14	119.7
C2—C3—H3	120.5	C20—C15—C16	118.60 (12)
C3—C4—C5	119.45 (12)	C20—C15—C8	121.58 (12)
C3—C4—C9	120.87 (11)	C16—C15—C8	119.82 (12)
C5—C4—C9	119.67 (11)	C17—C16—C15	120.44 (13)
C6—C5—C4	122.43 (12)	C17—C16—H16	119.8
C6—C5—H5	118.8	C15—C16—H16	119.8
C4—C5—H5	118.8	C18—C17—C16	121.14 (14)
C7—C6—C5	116.14 (12)	C18—C17—H17	119.4
C7—C6—H6	121.9	C16—C17—H17	119.4
C5—C6—H6	121.9	C19—C18—C17	117.29 (13)
O1—C7—C6	125.91 (11)	C19—C18—H18	121.4
O1—C7—C2	110.53 (11)	C17—C18—H18	121.4
C6—C7—C2	123.56 (12)	F1—C19—C18	118.41 (12)
C1—C8—O1	110.66 (11)	F1—C19—C20	117.96 (13)
C1—C8—C15	135.74 (12)	C18—C19—C20	123.63 (13)
O1—C8—C15	113.59 (11)	C19—C20—C15	118.90 (12)
C10—C9—C14	118.30 (12)	C19—C20—H20	120.6
C10—C9—C4	120.71 (11)	C15—C20—H20	120.6
C14—C9—C4	120.98 (12)	S1—C21—H21A	109.5
C11—C10—C9	120.88 (12)	S1—C21—H21B	109.5
C11—C10—H10	119.6	H21A—C21—H21B	109.5
C9—C10—H10	119.6	S1—C21—H21C	109.5
C12—C11—C10	120.04 (13)	H21A—C21—H21C	109.5
C12—C11—H11	120.0	H21B—C21—H21C	109.5

C21—S1—C1—C8	100.68 (13)	C3—C4—C9—C10	32.27 (18)
C21—S1—C1—C2	−81.81 (12)	C5—C4—C9—C10	−146.70 (13)
C8—C1—C2—C7	−0.32 (13)	C3—C4—C9—C14	−148.48 (13)
S1—C1—C2—C7	−178.30 (9)	C5—C4—C9—C14	32.55 (18)
C8—C1—C2—C3	178.54 (13)	C14—C9—C10—C11	−0.8 (2)
S1—C1—C2—C3	0.6 (2)	C4—C9—C10—C11	178.47 (13)
C7—C2—C3—C4	−0.78 (18)	C9—C10—C11—C12	0.3 (2)
C1—C2—C3—C4	−179.52 (13)	C10—C11—C12—C13	0.5 (2)
C2—C3—C4—C5	0.00 (18)	C11—C12—C13—C14	−0.7 (3)
C2—C3—C4—C9	−178.97 (11)	C12—C13—C14—C9	0.1 (2)
C3—C4—C5—C6	0.65 (19)	C10—C9—C14—C13	0.6 (2)
C9—C4—C5—C6	179.63 (12)	C4—C9—C14—C13	−178.66 (14)
C4—C5—C6—C7	−0.48 (19)	C1—C8—C15—C20	2.0 (2)
C8—O1—C7—C6	−179.95 (12)	O1—C8—C15—C20	−178.56 (11)
C8—O1—C7—C2	−0.27 (13)	C1—C8—C15—C16	−177.34 (14)
C5—C6—C7—O1	179.30 (12)	O1—C8—C15—C16	2.05 (17)
C5—C6—C7—C2	−0.4 (2)	C20—C15—C16—C17	−0.3 (2)
C3—C2—C7—O1	−178.71 (10)	C8—C15—C16—C17	179.10 (13)
C1—C2—C7—O1	0.36 (14)	C15—C16—C17—C18	−0.3 (2)
C3—C2—C7—C6	0.99 (19)	C16—C17—C18—C19	0.5 (2)
C1—C2—C7—C6	−179.94 (12)	C17—C18—C19—F1	179.64 (13)
C2—C1—C8—O1	0.17 (14)	C17—C18—C19—C20	−0.1 (2)
S1—C1—C8—O1	178.03 (9)	F1—C19—C20—C15	179.80 (11)
C2—C1—C8—C15	179.58 (14)	C18—C19—C20—C15	−0.4 (2)
S1—C1—C8—C15	−2.6 (2)	C16—C15—C20—C19	0.63 (19)
C7—O1—C8—C1	0.05 (13)	C8—C15—C20—C19	−178.76 (12)
C7—O1—C8—C15	−179.50 (10)

Experimental details

Crystal data
Chemical formula	C₂₁H₁₅FOS
M_r	334.39
Crystal system, space group	Triclinic, P1
Temperature (K)	296
a, b, c (Å)	4.7692 (1), 9.6442 (2), 17.4049 (3)
α, β, γ (°)	89.7700 (1), 87.589 (1), 80.061 (1)
V (Å³)	787.82 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.22
Crystal size (mm)	0.34 × 0.25 × 0.12

Data collection
Diffractometer	Bruker SMART APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.929, 0.974
No. of measured, independent and observed [I > 2σ(I)] reflections	13895, 3590, 3234
R_int	0.023
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.034, 0.091, 1.04
No. of reflections	3590
No. of parameters	218
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.30, −0.25

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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