5-Chloro-3-(4-fluoro­phenyl­sulfon­yl)-2,7-dimethyl-1-benzo­furan

Choi, H.D.; Lee, U.

doi:10.1107/S1600536814019114

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 70| Part 9| September 2014| Pages o1065-o1066

doi:10.1107/S1600536814019114

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5-Chloro-3-(4-fluorophenylsulfonyl)-2,7-dimethyl-1-benzofuran

Hong Dae Choi ^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

Edited by J. T. Mague, Tulane University, USA (Received 5 August 2014; accepted 24 August 2014; online 30 August 2014)

In the title compound, C₁₆H₁₂ClFO₃S, the dihedral angle between the plane of the benzofuran ring system [r.m.s. deviation = 0.007 (1) Å] and that of the 4-fluorophenyl ring is 76.11 (5)°. In the crystal, molecules are linked into [010] chains via two different inversion-generated pairs of C—H⋯O hydrogen bonds. The crystal structure also exhibits weak π–π interactions between the benzene and furan rings of neighbouring molecules [centroid–centroid distance = 3.820 (2) Å].

Keywords: crystal structure; benzofuran; 4-fluorophenyl; C–H⋯O hydrogen bonds; π–π interactions.

CCDC reference: 1020842

1. Related literature

For the pharmaceutical properties of compounds containing benzofuran moieties, see: Aslam et al. (2009 ); Galal et al. (2009 ); Howlett et al. (1999 ); Khan et al. (2005 ); Ono et al. (2002 ). For natural products with a benzofuran ring, see: Akgul & Anil (2003 ); Soekamto et al. (2003 ). For the synthesis of the starting material 5-chloro-3-(4-fluorophenylsulfanyl)-2,7-dimethyl-1-benzofuran, see: Choi et al. (1999 ). For a related structure, see: Choi et al. (2014 ).

2. Experimental

2.1. Crystal data

C₁₆H₁₂ClFO₃S
M_r = 338.77
Triclinic, $[P \overline 1]$
a = 8.4338 (3) Å
b = 9.9171 (3) Å
c = 10.1059 (3) Å
α = 73.988 (2)°
β = 66.155 (2)°
γ = 73.629 (2)°
V = 729.02 (4) Å³
Z = 2
Mo Kα radiation
μ = 0.43 mm⁻¹
T = 173 K
0.47 × 0.31 × 0.15 mm

2.2. Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.825, T_max = 0.939
13460 measured reflections
3614 independent reflections
3163 reflections with I > 2σ(I)
R_int = 0.027

2.3. Refinement

R[F² > 2σ(F²)] = 0.037
wR(F²) = 0.098
S = 1.03
3614 reflections
202 parameters
H-atom parameters constrained
Δρ_max = 0.34 e Å⁻³
Δρ_min = −0.37 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C9—H9C⋯O2ⁱ	0.98	2.57	3.331 (2)	135
C16—H16⋯O3ⁱⁱ	0.95	2.53	3.230 (2)	130
Symmetry codes: (i) -x, -y+1, -z+1; (ii) -x, -y+2, -z.

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: 1020842

Crystal structure: contains datablock I. DOI: 10.1107/S1600536814019114/mw2126sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536814019114/mw2126Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536814019114/mw2126Isup3.cml

checkCIF report

Comment top

Molecules containing the benzofuran skeleton show interesting pharmacological properties such as antibacterial, antifungal, antitumor, antiviral and antimicrobial activities (Aslam et al. 2009, Galal et al., 2009, Khan et al., 2005) as well as being potential inhibitors of β-amyloid aggregation (Howlett et al., 1999, Ono et al., 2002). These benzofuran compounds are widely occurring in nature (Akgul & Anil, 2003, Soekamto et al., 2003). As a part of our ongoing project of 3-arylsulfonyl-5-chloro-2,7-dimethyl-1-benzofuran derivatives containing a 3-methylphenylsulfonyl substituent in the 3-position (Choi et al., 2014), we report herein on 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 4-fluorophenyl ring is essentially planar, with a mean deviation of 0.003 (1) Å from the least-squares plane defined by the six constituent atoms. The dihedral angle formed by the benzofuran ring system and the 4-fluorophenyl ring is 76.11 (5)°. In the crystal structure (Fig. 2), molecules are linked via pairs of C—H···O hydrogen bonds (Table 1), forming inversion dimers. The crystal packing (Fig. 2) also exhibits weak π–π interactions between the benzene and furan rings of neighbouring molecules, with a Cg1···Cg2ⁱ (i: -x, 1-y, 1-z) distance of 3.820 (2) Å and an interplanar distance of 3.641 (2) Å resulting in a slippage of 1.159 (2) Å (Cg1 and Cg2 are the centroids of the C2–C7 benzene ring and the C1/C2/C7/O1/C8 furan ring, respectively),

Related literature top

For the pharmaceutical properties of compounds containing benzofuran moieties, see: Aslam et al. (2009); Galal et al. (2009); Howlett et al. (1999); Khan et al. (2005); Ono et al. (2002). For natural products with a benzofuran ring, see: Akgul & Anil (2003); Soekamto et al. (2003). For the synthesis of the starting material 5-chloro-3-(4-fluorophenylsulfanyl)-2,7-dimethyl-1-benzofuran, see: Choi et al. (1999). For a related structure, see: Choi et al. (2014).

Experimental top

The starting material 5-chloro-3-(4-fluorophenylsulfanyl)-2,7-dimethyl-1-benzofuran was prepared by the literature method (Choi et al., 1999). 3-Chloroperoxybenzoic acid (77%, 515 mg, 2.3 mmol) was added in small portions to a stirred solution of 5-chloro-3-(4-fluorophenylsulfanyl)-2,7-dimethyl-1-benzofuran (337 mg, 1.1 mmol) in dichloromethane (35 mL) at 273 K. After being stirred at room temperature for 10h, the mixture was washed with saturated sodium bicarbonate solution (2 x 20 mL) 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% (240 mg); m.p. 468–469 K; R_f = 0.56 (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 (30 mg) in ethyl acetate (20 mL) 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 for Windows (Farrugia, 2012) and DIAMOND (Brandenburg, 1998); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of 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 the C—H···O and π–π interactions (dotted lines) in the crystal structure of the title compound. H atoms non-participating in hydrogen-bonding were omitted for clarity. [Symmetry codes: (i) - x, - y + 1, - z + 1; (ii) - x, - y + 2, - z.]

5-Chloro-3-(4-fluorophenylsulfonyl)-2,7-dimethyl-1-benzofuran top

Crystal data top

C₁₆H₁₂ClFO₃S	Z = 2
M_r = 338.77	F(000) = 348
Triclinic, P1	D_x = 1.543 Mg m⁻³
Hall symbol: -P 1	Melting point = 469–468 K
a = 8.4338 (3) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.9171 (3) Å	Cell parameters from 5949 reflections
c = 10.1059 (3) Å	θ = 2.2–28.3°
α = 73.988 (2)°	µ = 0.43 mm⁻¹
β = 66.155 (2)°	T = 173 K
γ = 73.629 (2)°	Block, colourless
V = 729.02 (4) Å³	0.47 × 0.31 × 0.15 mm

Data collection top

Bruker SMART APEXII CCD diffractometer	3614 independent reflections
Radiation source: rotating anode	3163 reflections with I > 2σ(I)
Graphite multilayer monochromator	R_int = 0.027
Detector resolution: 10.0 pixels mm^-1	θ_max = 28.3°, θ_min = 2.2°
ϕ and ω scans	h = −10→11
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −13→13
T_min = 0.825, T_max = 0.939	l = −13→13
13460 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)] = 0.037	H-atom parameters constrained
wR(F²) = 0.098	w = 1/[σ²(F_o²) + (0.0444P)² + 0.4675P] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max = 0.001
3614 reflections	Δρ_max = 0.34 e Å⁻³
202 parameters	Δρ_min = −0.37 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: 0.016 (2)

Crystal data top

C₁₆H₁₂ClFO₃S	γ = 73.629 (2)°
M_r = 338.77	V = 729.02 (4) Å³
Triclinic, P1	Z = 2
a = 8.4338 (3) Å	Mo Kα radiation
b = 9.9171 (3) Å	µ = 0.43 mm⁻¹
c = 10.1059 (3) Å	T = 173 K
α = 73.988 (2)°	0.47 × 0.31 × 0.15 mm
β = 66.155 (2)°

Data collection top

Bruker SMART APEXII CCD diffractometer	3614 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	3163 reflections with I > 2σ(I)
T_min = 0.825, T_max = 0.939	R_int = 0.027
13460 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.037	0 restraints
wR(F²) = 0.098	H-atom parameters constrained
S = 1.03	Δρ_max = 0.34 e Å⁻³
3614 reflections	Δρ_min = −0.37 e Å⁻³
202 parameters

Special details top

Experimental. 1H NMR (δ p.p.m., CDCl₃, 400 Hz): 7.98-8.03 (m, 2H), 7.67 (d, J = 2.04 Hz, 1H), 7.17-7.22 (m, 2H), 7.10 (s, 1H), 2.80 (s, 3H), 2.43 (s, 3H).

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	0.51698 (6)	0.19310 (5)	0.47396 (5)	0.03701 (14)
S1	0.13342 (5)	0.69006 (4)	0.14183 (4)	0.02143 (12)
F1	0.70966 (17)	0.98587 (15)	−0.25209 (14)	0.0518 (4)
O1	0.04838 (15)	0.74576 (13)	0.53640 (13)	0.0263 (3)
O2	0.18910 (16)	0.54497 (12)	0.11860 (13)	0.0272 (3)
O3	−0.02442 (16)	0.77606 (13)	0.11823 (13)	0.0291 (3)
C1	0.1165 (2)	0.68330 (17)	0.32016 (17)	0.0215 (3)
C2	0.2069 (2)	0.56854 (17)	0.40420 (17)	0.0217 (3)
C3	0.3177 (2)	0.43625 (17)	0.38227 (18)	0.0235 (3)
H3	0.3506	0.4013	0.2943	0.028*
C4	0.3767 (2)	0.35884 (18)	0.49555 (19)	0.0260 (3)
C5	0.3304 (2)	0.40691 (19)	0.62598 (19)	0.0285 (4)
H5	0.3761	0.3492	0.6996	0.034*
C6	0.2188 (2)	0.53740 (19)	0.65043 (18)	0.0267 (4)
C7	0.1604 (2)	0.61368 (18)	0.53606 (18)	0.0236 (3)
C8	0.0241 (2)	0.78571 (18)	0.40404 (18)	0.0240 (3)
C9	0.1674 (3)	0.5919 (2)	0.78961 (19)	0.0361 (4)
H9A	0.1210	0.6950	0.7737	0.054*
H9B	0.2713	0.5730	0.8175	0.054*
H9C	0.0764	0.5431	0.8685	0.054*
C10	−0.0915 (2)	0.92612 (19)	0.3815 (2)	0.0322 (4)
H10A	−0.0361	1.0018	0.3790	0.048*
H10B	−0.2059	0.9286	0.4625	0.048*
H10C	−0.1092	0.9411	0.2881	0.048*
C11	0.3084 (2)	0.78021 (17)	0.02639 (17)	0.0224 (3)
C12	0.4815 (2)	0.70757 (19)	0.0003 (2)	0.0306 (4)
H12	0.5062	0.6108	0.0468	0.037*
C13	0.6181 (3)	0.7776 (2)	−0.0943 (2)	0.0374 (4)
H13	0.7379	0.7301	−0.1138	0.045*
C14	0.5764 (3)	0.9174 (2)	−0.1594 (2)	0.0339 (4)
C15	0.4069 (3)	0.9914 (2)	−0.1352 (2)	0.0348 (4)
H15	0.3834	1.0880	−0.1825	0.042*
C16	0.2703 (2)	0.92165 (19)	−0.03976 (19)	0.0299 (4)
H16	0.1511	0.9706	−0.0198	0.036*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0373 (3)	0.0245 (2)	0.0429 (3)	−0.00018 (18)	−0.0175 (2)	0.00258 (18)
S1	0.0238 (2)	0.0211 (2)	0.01966 (19)	−0.00243 (15)	−0.00994 (15)	−0.00263 (14)
F1	0.0438 (7)	0.0607 (9)	0.0443 (7)	−0.0292 (7)	0.0018 (5)	−0.0068 (6)
O1	0.0261 (6)	0.0302 (6)	0.0231 (6)	−0.0035 (5)	−0.0074 (5)	−0.0100 (5)
O2	0.0366 (7)	0.0233 (6)	0.0244 (6)	−0.0044 (5)	−0.0133 (5)	−0.0062 (5)
O3	0.0253 (6)	0.0319 (7)	0.0299 (6)	−0.0029 (5)	−0.0148 (5)	−0.0005 (5)
C1	0.0220 (7)	0.0222 (8)	0.0199 (7)	−0.0032 (6)	−0.0077 (6)	−0.0042 (6)
C2	0.0229 (7)	0.0233 (8)	0.0186 (7)	−0.0066 (6)	−0.0072 (6)	−0.0015 (6)
C3	0.0250 (8)	0.0225 (8)	0.0216 (8)	−0.0042 (6)	−0.0082 (6)	−0.0025 (6)
C4	0.0252 (8)	0.0218 (8)	0.0285 (8)	−0.0057 (6)	−0.0106 (6)	0.0022 (6)
C5	0.0307 (9)	0.0319 (9)	0.0234 (8)	−0.0122 (7)	−0.0135 (7)	0.0063 (7)
C6	0.0280 (8)	0.0350 (9)	0.0190 (7)	−0.0138 (7)	−0.0076 (6)	−0.0010 (6)
C7	0.0221 (8)	0.0264 (8)	0.0217 (8)	−0.0063 (6)	−0.0053 (6)	−0.0056 (6)
C8	0.0224 (8)	0.0262 (8)	0.0245 (8)	−0.0045 (6)	−0.0086 (6)	−0.0062 (6)
C9	0.0388 (10)	0.0529 (12)	0.0211 (8)	−0.0162 (9)	−0.0100 (7)	−0.0075 (8)
C10	0.0290 (9)	0.0281 (9)	0.0395 (10)	0.0031 (7)	−0.0131 (8)	−0.0134 (8)
C11	0.0243 (8)	0.0240 (8)	0.0188 (7)	−0.0036 (6)	−0.0079 (6)	−0.0042 (6)
C12	0.0262 (9)	0.0245 (9)	0.0385 (10)	0.0002 (7)	−0.0105 (7)	−0.0084 (7)
C13	0.0257 (9)	0.0379 (11)	0.0455 (11)	−0.0041 (8)	−0.0049 (8)	−0.0168 (9)
C14	0.0347 (10)	0.0410 (11)	0.0260 (9)	−0.0166 (8)	−0.0031 (7)	−0.0084 (8)
C15	0.0421 (11)	0.0321 (10)	0.0291 (9)	−0.0124 (8)	−0.0145 (8)	0.0045 (7)
C16	0.0299 (9)	0.0277 (9)	0.0290 (9)	−0.0034 (7)	−0.0131 (7)	0.0012 (7)

Geometric parameters (Å, º) top

Cl1—C4	1.7440 (18)	C6—C9	1.501 (2)
S1—O3	1.4356 (12)	C8—C10	1.477 (2)
S1—O2	1.4361 (12)	C9—H9A	0.9800
S1—C1	1.7332 (16)	C9—H9B	0.9800
S1—C11	1.7648 (16)	C9—H9C	0.9800
F1—C14	1.353 (2)	C10—H10A	0.9800
O1—C8	1.368 (2)	C10—H10B	0.9800
O1—C7	1.382 (2)	C10—H10C	0.9800
C1—C8	1.361 (2)	C11—C16	1.386 (2)
C1—C2	1.448 (2)	C11—C12	1.386 (2)
C2—C7	1.392 (2)	C12—C13	1.385 (3)
C2—C3	1.395 (2)	C12—H12	0.9500
C3—C4	1.382 (2)	C13—C14	1.374 (3)
C3—H3	0.9500	C13—H13	0.9500
C4—C5	1.394 (3)	C14—C15	1.366 (3)
C5—C6	1.387 (3)	C15—C16	1.385 (2)
C5—H5	0.9500	C15—H15	0.9500
C6—C7	1.385 (2)	C16—H16	0.9500

O3—S1—O2	119.75 (8)	C6—C9—H9A	109.5
O3—S1—C1	109.59 (8)	C6—C9—H9B	109.5
O2—S1—C1	106.33 (7)	H9A—C9—H9B	109.5
O3—S1—C11	107.27 (8)	C6—C9—H9C	109.5
O2—S1—C11	107.36 (8)	H9A—C9—H9C	109.5
C1—S1—C11	105.71 (8)	H9B—C9—H9C	109.5
C8—O1—C7	107.05 (12)	C8—C10—H10A	109.5
C8—C1—C2	107.60 (14)	C8—C10—H10B	109.5
C8—C1—S1	126.93 (13)	H10A—C10—H10B	109.5
C2—C1—S1	125.40 (12)	C8—C10—H10C	109.5
C7—C2—C3	119.54 (15)	H10A—C10—H10C	109.5
C7—C2—C1	104.59 (14)	H10B—C10—H10C	109.5
C3—C2—C1	135.87 (15)	C16—C11—C12	121.04 (16)
C4—C3—C2	116.27 (15)	C16—C11—S1	119.36 (13)
C4—C3—H3	121.9	C12—C11—S1	119.58 (13)
C2—C3—H3	121.9	C13—C12—C11	119.27 (17)
C3—C4—C5	123.25 (16)	C13—C12—H12	120.4
C3—C4—Cl1	118.38 (14)	C11—C12—H12	120.4
C5—C4—Cl1	118.37 (13)	C14—C13—C12	118.39 (18)
C6—C5—C4	121.29 (16)	C14—C13—H13	120.8
C6—C5—H5	119.4	C12—C13—H13	120.8
C4—C5—H5	119.4	F1—C14—C15	118.07 (18)
C7—C6—C5	114.81 (15)	F1—C14—C13	118.47 (18)
C7—C6—C9	122.84 (17)	C15—C14—C13	123.45 (17)
C5—C6—C9	122.34 (16)	C14—C15—C16	118.13 (18)
O1—C7—C6	124.81 (15)	C14—C15—H15	120.9
O1—C7—C2	110.37 (14)	C16—C15—H15	120.9
C6—C7—C2	124.83 (16)	C15—C16—C11	119.71 (17)
C1—C8—O1	110.39 (15)	C15—C16—H16	120.1
C1—C8—C10	133.98 (16)	C11—C16—H16	120.1
O1—C8—C10	115.63 (14)

O3—S1—C1—C8	−29.69 (17)	C1—C2—C7—O1	0.51 (17)
O2—S1—C1—C8	−160.47 (15)	C3—C2—C7—C6	1.2 (2)
C11—S1—C1—C8	85.62 (16)	C1—C2—C7—C6	−179.20 (15)
O3—S1—C1—C2	153.51 (13)	C2—C1—C8—O1	0.14 (18)
O2—S1—C1—C2	22.72 (16)	S1—C1—C8—O1	−177.13 (11)
C11—S1—C1—C2	−91.19 (15)	C2—C1—C8—C10	179.67 (18)
C8—C1—C2—C7	−0.40 (18)	S1—C1—C8—C10	2.4 (3)
S1—C1—C2—C7	176.93 (12)	C7—O1—C8—C1	0.18 (18)
C8—C1—C2—C3	179.10 (17)	C7—O1—C8—C10	−179.45 (14)
S1—C1—C2—C3	−3.6 (3)	O3—S1—C11—C16	13.38 (16)
C7—C2—C3—C4	−1.0 (2)	O2—S1—C11—C16	143.30 (14)
C1—C2—C3—C4	179.57 (17)	C1—S1—C11—C16	−103.50 (15)
C2—C3—C4—C5	0.2 (2)	O3—S1—C11—C12	−164.96 (14)
C2—C3—C4—Cl1	−179.55 (12)	O2—S1—C11—C12	−35.04 (16)
C3—C4—C5—C6	0.6 (3)	C1—S1—C11—C12	78.15 (15)
Cl1—C4—C5—C6	−179.72 (13)	C16—C11—C12—C13	−0.5 (3)
C4—C5—C6—C7	−0.4 (2)	S1—C11—C12—C13	177.85 (14)
C4—C5—C6—C9	−179.76 (16)	C11—C12—C13—C14	−0.2 (3)
C8—O1—C7—C6	179.28 (15)	C12—C13—C14—F1	−179.88 (17)
C8—O1—C7—C2	−0.44 (17)	C12—C13—C14—C15	0.4 (3)
C5—C6—C7—O1	179.86 (14)	F1—C14—C15—C16	−179.67 (17)
C9—C6—C7—O1	−0.8 (3)	C13—C14—C15—C16	0.1 (3)
C5—C6—C7—C2	−0.5 (2)	C14—C15—C16—C11	−0.7 (3)
C9—C6—C7—C2	178.89 (16)	C12—C11—C16—C15	0.9 (3)
C3—C2—C7—O1	−179.08 (13)	S1—C11—C16—C15	−177.40 (14)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9C···O2ⁱ	0.98	2.57	3.331 (2)	135
C16—H16···O3ⁱⁱ	0.95	2.53	3.230 (2)	130

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9C···O2ⁱ	0.98	2.57	3.331 (2)	135
C16—H16···O3ⁱⁱ	0.95	2.53	3.230 (2)	130

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

Acknowledgements

The X-ray centre of the Gyeongsang National University is acknowledged for providing access to the single-crystal diffractometer.

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