3-(3-Chloro-4-methyl­phen­yl)-2-(4-fluoro­phen­yl)thia­zolidin-4-one

Sun, X.-J.; Zhou, J.-F.

doi:10.1107/S1600536807057133

organic compounds

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ISSN: 2056-9890

Volume 64| Part 1| January 2008| Page o214

https://doi.org/10.1107/S1600536807057133

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3-(3-Chloro-4-methylphenyl)-2-(4-fluorophenyl)thiazolidin-4-one

Xiao-Jun Sun ^a ^* and Jian-Feng Zhou ^a

^aJiangsu Key Laboratory of Chemistry of Low-Dimensional Materials, Department of Chemistry, Huaiyin Teachers' College, Huaian 223300, People's Republic of China
^*Correspondence e-mail: sunxiaojun100@126.com.cn

(Received 27 October 2007; accepted 8 November 2007; online 6 December 2007)

The title compound, C₁₆H₁₃ClFNOS, possesses potent antibacterial activity. The overall molecular conformation is described by the dihedral angles of 43.0 (1)° between the 3-chloro-4-methylbenzene and thiazolidinone rings, and 88.8 (5)° between the thiazolidinone and 4-fluorobenzene rings. The 3-chloro-4-methylbenzene ring is disordered over two positions with occupancy factors approximately 3:1.

Related literature

For related literature, see: Tumul Srivastava et al. (2002 ).

Experimental

Crystal data

C₁₆H₁₃ClFNOS
M_r = 321.78
Orthorhombic, P b c a
a = 12.265 (3) Å
b = 12.994 (3) Å
c = 18.192 (4) Å
V = 2899.3 (10) Å³
Z = 8
Mo Kα radiation
μ = 0.42 mm⁻¹
T = 113 (2) K
0.16 × 0.14 × 0.10 mm

Data collection

Rigaku Saturn diffractometer
Absorption correction: multi-scan (Jacobson, 1998 ) T_min = 0.937, T_max = 0.960
34208 measured reflections
3445 independent reflections
2796 reflections with I > 2σ(I)
R_int = 0.056

Refinement

R[F² > 2σ(F²)] = 0.048
wR(F²) = 0.125
S = 1.12
3445 reflections
240 parameters
8 restraints
H-atom parameters constrained
Δρ_max = 0.38 e Å⁻³
Δρ_min = −0.76 e Å⁻³

Data collection: CrystalClear (Rigaku/MSC, 2005 ); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997 ); molecular graphics: SHELXL97; software used to prepare material for publication: CrystalStructure (Rigaku/MSC, 2005).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536807057133/kp2144sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536807057133/kp2144Isup2.hkl

checkCIF report

Comment top

In recent years, 4-thiazolidinones are the most extensively investigated class of compounds, which exhibits various biological activities, such as anticancer, antitubercular, antibacterial and herbicidal activities. In view of these properties and in a continuation of our interest in the chemistry of 4-thiazolidinones, we have attempted to synthesize a series of 4-thiazolidinone derivatives, some of which have comparatively high antibacterial activity.The crystal structure determination of the title compound, (I), was undertaken to investigate the relationship between structure and antibacterial activity (Fig. 1). The molecular conformation is described by the dihedral angle between 3-chloro-4-methylbenzene ring and thiazolidinone ring of 43.0 (1)° and the dihedral angle between thiazolidinone ring and 4-fluorobenzene ring of 88.8 (5)°.

Related literature top

For related literature, see: Tumul Srivastava, Haq & Katti (2002).

Experimental top

Compound (I) was synthesized according to the procedure of Tumul Srivastava et al. (2002). A crystal of (I) suitable for X-ray analysis was grown from an ethanol solution by slow evaporation at room temperature.

Structure description top

For related literature, see: Tumul Srivastava, Haq & Katti (2002).

Computing details top

Data collection: CrystalClear (Rigaku/MSC, 2005); cell refinement: CrystalClear (Rigaku/MSC, 2005); data reduction: CrystalClear (Rigaku/MSC, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXL97 (Sheldrick, 1997); software used to prepare material for publication: CrystalStructure (Rigaku/MSC, 2005).

Figures top

Fig. 1. The molecular structure of (I) showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level and H atoms are shown as small spheres of arbitrary radii. Only the major component of the disorder is shown.

3-(3-Chloro-4-methylphenyl)-2-(4-fluorophenyl)thiazolidin-4-one top

Crystal data top

C₁₆H₁₃ClFNOS	D_x = 1.474 Mg m⁻³
M_r = 321.78	Mo Kα radiation, λ = 0.71070 Å
Orthorhombic, Pbca	Cell parameters from 6992 reflections
a = 12.265 (3) Å	θ = 2.0–27.9°
b = 12.994 (3) Å	µ = 0.42 mm⁻¹
c = 18.192 (4) Å	T = 113 K
V = 2899.3 (10) Å³	Block, colourless
Z = 8	0.16 × 0.14 × 0.10 mm
F(000) = 1328

Data collection top

Rigaku Saturn diffractometer	3445 independent reflections
Radiation source: Rotating anode	2796 reflections with I > 2σ(I)
Confocal monochromator	R_int = 0.056
Detector resolution: 7.31 pixels mm^-1	θ_max = 27.9°, θ_min = 2.5°
ω scans	h = −16→15
Absorption correction: multi-scan (Jacobson, 1998)	k = −17→17
T_min = 0.937, T_max = 0.960	l = −23→23
34208 measured reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.048	H-atom parameters constrained
wR(F²) = 0.125	w = 1/[σ²(F_o²) + (0.0666P)² + 0.3972P] where P = (F_o² + 2F_c²)/3
S = 1.12	(Δ/σ)_max = 0.001
3445 reflections	Δρ_max = 0.38 e Å⁻³
240 parameters	Δρ_min = −0.76 e Å⁻³
8 restraints	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0157 (15)

Crystal data top

C₁₆H₁₃ClFNOS	V = 2899.3 (10) Å³
M_r = 321.78	Z = 8
Orthorhombic, Pbca	Mo Kα radiation
a = 12.265 (3) Å	µ = 0.42 mm⁻¹
b = 12.994 (3) Å	T = 113 K
c = 18.192 (4) Å	0.16 × 0.14 × 0.10 mm

Data collection top

Rigaku Saturn diffractometer	3445 independent reflections
Absorption correction: multi-scan (Jacobson, 1998)	2796 reflections with I > 2σ(I)
T_min = 0.937, T_max = 0.960	R_int = 0.056
34208 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.048	8 restraints
wR(F²) = 0.125	H-atom parameters constrained
S = 1.12	Δρ_max = 0.38 e Å⁻³
3445 reflections	Δρ_min = −0.76 e Å⁻³
240 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	Occ. (<1)
S1	0.30373 (5)	0.52351 (4)	0.39652 (3)	0.0435 (2)
F1	0.49210 (13)	0.10913 (11)	0.54723 (7)	0.0612 (4)
O1	0.09023 (11)	0.42265 (11)	0.25825 (7)	0.0344 (3)
N1	0.25973 (12)	0.37796 (11)	0.29988 (7)	0.0258 (3)
C1	0.16844 (15)	0.43791 (14)	0.29819 (9)	0.0265 (4)
C2	0.17362 (16)	0.52700 (14)	0.35115 (10)	0.0299 (4)
H2A	0.1142	0.5215	0.3878	0.036*
H2B	0.1650	0.5928	0.3243	0.036*
C3	0.35104 (15)	0.40902 (14)	0.34646 (9)	0.0262 (4)
H3A	0.4140	0.4287	0.3145	0.031*
C4	0.38717 (14)	0.32583 (13)	0.39887 (8)	0.0226 (4)
C5	0.31314 (15)	0.27742 (14)	0.44550 (9)	0.0270 (4)
H5A	0.2380	0.2950	0.4430	0.032*
C6	0.34782 (18)	0.20378 (14)	0.49557 (10)	0.0342 (4)
H6A	0.2977	0.1707	0.5276	0.041*
C7	0.45733 (18)	0.18018 (15)	0.49737 (10)	0.0374 (5)
C8	0.53130 (18)	0.22326 (18)	0.45151 (10)	0.0408 (5)
H8A	0.6058	0.2034	0.4535	0.049*
C9	0.49613 (16)	0.29727 (17)	0.40134 (10)	0.0332 (4)
H9A	0.5469	0.3283	0.3687	0.040*
Cl1	0.10556 (6)	0.05302 (5)	0.18509 (4)	0.0425 (3)	0.7369 (16)
C10	0.2796 (3)	0.2928 (2)	0.2516 (2)	0.0241 (9)	0.7369 (16)
C11	0.3781 (2)	0.2805 (2)	0.21479 (19)	0.0251 (7)	0.7369 (16)
H11A	0.4354	0.3287	0.2220	0.030*	0.7369 (16)
C12	0.39283 (18)	0.19757 (18)	0.16753 (13)	0.0284 (7)	0.7369 (16)
H12A	0.4601	0.1891	0.1424	0.034*	0.7369 (16)
C13	0.3091 (2)	0.12703 (14)	0.15704 (10)	0.0273 (7)	0.7369 (16)
C14	0.2106 (2)	0.13939 (18)	0.19381 (13)	0.0285 (7)	0.7369 (16)
C15	0.1959 (2)	0.2223 (2)	0.24107 (18)	0.0259 (7)	0.7369 (16)
H15A	0.1286	0.2307	0.2662	0.031*	0.7369 (16)
C16	0.3251 (3)	0.0370 (2)	0.10336 (15)	0.0426 (8)	0.7369 (16)
H16A	0.3988	0.0398	0.0827	0.064*	0.7369 (16)
H16B	0.2715	0.0420	0.0636	0.064*	0.7369 (16)
H16C	0.3152	−0.0282	0.1296	0.064*	0.7369 (16)
Cl1'	0.46197 (17)	0.13594 (14)	0.12449 (10)	0.0381 (6)	0.2631 (16)
C10'	0.2546 (8)	0.2828 (6)	0.2566 (6)	0.023 (2)	0.2631 (16)
C11'	0.1642 (6)	0.2184 (6)	0.2549 (5)	0.0210 (18)	0.2631 (16)
H11B	0.1016	0.2344	0.2834	0.025*	0.2631 (16)
C12'	0.1654 (5)	0.1304 (5)	0.2114 (4)	0.032 (2)	0.2631 (16)
H12B	0.1036	0.0864	0.2102	0.039*	0.2631 (16)
C13'	0.2570 (6)	0.1070 (4)	0.1696 (3)	0.0234 (17)	0.2631 (16)
C14'	0.3474 (5)	0.1714 (5)	0.1714 (3)	0.0197 (16)	0.2631 (16)
C15'	0.3462 (6)	0.2594 (6)	0.2149 (5)	0.025 (2)	0.2631 (16)
H15B	0.4080	0.3034	0.2161	0.030*	0.2631 (16)
C16'	0.2502 (9)	0.0116 (6)	0.1187 (4)	0.0398 (19)	0.2631 (16)
H16D	0.1796	−0.0224	0.1256	0.060*	0.2631 (16)
H16E	0.3090	−0.0364	0.1310	0.060*	0.2631 (16)
H16F	0.2576	0.0334	0.0674	0.060*	0.2631 (16)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0665 (4)	0.0283 (3)	0.0359 (3)	0.0119 (2)	−0.0239 (2)	−0.0098 (2)
F1	0.1027 (12)	0.0462 (8)	0.0347 (7)	0.0305 (8)	−0.0128 (7)	0.0098 (6)
O1	0.0335 (8)	0.0393 (8)	0.0304 (7)	0.0034 (6)	−0.0069 (6)	−0.0027 (6)
N1	0.0324 (8)	0.0268 (8)	0.0182 (7)	0.0040 (6)	−0.0049 (6)	−0.0040 (6)
C1	0.0331 (10)	0.0275 (9)	0.0189 (8)	0.0015 (7)	0.0007 (7)	0.0017 (7)
C2	0.0391 (11)	0.0276 (9)	0.0231 (9)	0.0023 (8)	0.0050 (8)	−0.0024 (7)
C3	0.0309 (10)	0.0275 (9)	0.0203 (8)	−0.0011 (7)	−0.0025 (7)	−0.0002 (7)
C4	0.0276 (9)	0.0239 (9)	0.0162 (8)	−0.0001 (7)	−0.0035 (6)	−0.0031 (6)
C5	0.0311 (10)	0.0287 (9)	0.0214 (8)	−0.0012 (7)	0.0002 (7)	−0.0020 (7)
C6	0.0544 (13)	0.0268 (10)	0.0215 (9)	−0.0049 (9)	0.0008 (8)	0.0008 (7)
C7	0.0608 (13)	0.0305 (10)	0.0208 (8)	0.0152 (9)	−0.0100 (9)	−0.0014 (7)
C8	0.0393 (11)	0.0550 (13)	0.0282 (10)	0.0179 (10)	−0.0080 (9)	−0.0035 (9)
C9	0.0302 (10)	0.0452 (12)	0.0241 (9)	0.0022 (8)	−0.0018 (7)	−0.0011 (8)
Cl1	0.0535 (5)	0.0304 (4)	0.0437 (4)	−0.0209 (3)	−0.0178 (3)	0.0066 (3)
C10	0.032 (2)	0.0235 (16)	0.0173 (16)	−0.0010 (13)	−0.0065 (14)	−0.0009 (13)
C11	0.0264 (18)	0.0251 (15)	0.0238 (14)	−0.0027 (13)	−0.0027 (13)	−0.0022 (11)
C12	0.0331 (18)	0.0302 (16)	0.0220 (13)	−0.0030 (13)	0.0025 (13)	−0.0013 (11)
C13	0.044 (2)	0.0207 (16)	0.0173 (13)	−0.0017 (14)	−0.0014 (14)	0.0039 (11)
C14	0.036 (2)	0.0262 (15)	0.0233 (16)	−0.0052 (15)	−0.0077 (14)	0.0044 (12)
C15	0.024 (2)	0.0317 (15)	0.0223 (16)	−0.0002 (13)	−0.0019 (13)	0.0028 (11)
C16	0.073 (2)	0.0288 (15)	0.0263 (14)	0.0019 (15)	−0.0060 (14)	−0.0073 (11)
Cl1'	0.0519 (12)	0.0304 (10)	0.0321 (10)	0.0123 (8)	0.0154 (8)	0.0041 (7)
C10'	0.014 (4)	0.037 (6)	0.018 (4)	0.015 (4)	−0.003 (3)	−0.004 (4)
C11'	0.020 (4)	0.026 (4)	0.018 (4)	0.006 (3)	0.000 (3)	−0.011 (3)
C12'	0.037 (6)	0.034 (5)	0.026 (4)	0.008 (4)	0.000 (4)	−0.008 (3)
C13'	0.027 (5)	0.021 (4)	0.023 (4)	−0.005 (4)	−0.004 (4)	0.009 (3)
C14'	0.023 (5)	0.016 (4)	0.020 (3)	0.000 (3)	0.008 (3)	0.001 (3)
C15'	0.020 (5)	0.036 (5)	0.018 (4)	−0.004 (4)	0.001 (3)	0.009 (3)
C16'	0.060 (6)	0.032 (4)	0.027 (4)	0.005 (4)	−0.014 (4)	−0.009 (3)

Geometric parameters (Å, º) top

S1—C2	1.797 (2)	C11—C12	1.3900
S1—C3	1.8382 (19)	C11—H11A	0.9500
F1—C7	1.363 (2)	C12—C13	1.3900
O1—C1	1.220 (2)	C12—H12A	0.9500
N1—C1	1.364 (2)	C13—C14	1.3900
N1—C10	1.434 (2)	C13—C16	1.537 (3)
N1—C3	1.461 (2)	C14—C15	1.3900
N1—C10'	1.467 (4)	C15—H15A	0.9500
C1—C2	1.507 (2)	C16—H16A	0.9800
C2—H2A	0.9900	C16—H16B	0.9800
C2—H2B	0.9900	C16—H16C	0.9800
C3—C4	1.508 (2)	Cl1'—C14'	1.707 (5)
C3—H3A	1.0000	C10'—C11'	1.3900
C4—C9	1.388 (3)	C10'—C15'	1.3900
C4—C5	1.393 (2)	C11'—C12'	1.3900
C5—C6	1.388 (3)	C11'—H11B	0.9500
C5—H5A	0.9500	C12'—C13'	1.3900
C6—C7	1.378 (3)	C12'—H12B	0.9500
C6—H6A	0.9500	C13'—C14'	1.3900
C7—C8	1.354 (3)	C13'—C16'	1.549 (7)
C8—C9	1.394 (3)	C14'—C15'	1.3900
C8—H8A	0.9500	C15'—H15B	0.9500
C9—H9A	0.9500	C16'—H16D	0.9800
Cl1—C14	1.716 (2)	C16'—H16E	0.9800
C10—C11	1.3900	C16'—H16F	0.9800
C10—C15	1.3900

C2—S1—C3	94.20 (8)	C12—C11—H11A	120.0
C1—N1—C10	124.5 (2)	C10—C11—H11A	120.0
C1—N1—C3	118.97 (14)	C11—C12—C13	120.0
C10—N1—C3	116.0 (2)	C11—C12—H12A	120.0
C1—N1—C10'	115.7 (5)	C13—C12—H12A	120.0
C10—N1—C10'	13.6 (4)	C12—C13—C14	120.0
C3—N1—C10'	125.2 (5)	C12—C13—C16	119.7 (2)
O1—C1—N1	124.48 (16)	C14—C13—C16	120.3 (2)
O1—C1—C2	122.60 (16)	C15—C14—C13	120.0
N1—C1—C2	112.92 (15)	C15—C14—Cl1	117.82 (16)
C1—C2—S1	108.15 (13)	C13—C14—Cl1	122.16 (16)
C1—C2—H2A	110.1	C14—C15—C10	120.0
S1—C2—H2A	110.1	C14—C15—H15A	120.0
C1—C2—H2B	110.1	C10—C15—H15A	120.0
S1—C2—H2B	110.1	C13—C16—H16A	109.5
H2A—C2—H2B	108.4	C13—C16—H16B	109.5
N1—C3—C4	113.20 (14)	H16A—C16—H16B	109.5
N1—C3—S1	105.60 (12)	C13—C16—H16C	109.5
C4—C3—S1	111.08 (11)	H16A—C16—H16C	109.5
N1—C3—H3A	108.9	H16B—C16—H16C	109.5
C4—C3—H3A	108.9	C11'—C10'—C15'	120.0
S1—C3—H3A	108.9	C11'—C10'—N1	123.7 (5)
C9—C4—C5	119.17 (16)	C15'—C10'—N1	116.3 (5)
C9—C4—C3	119.69 (16)	C10'—C11'—C12'	120.0
C5—C4—C3	121.14 (16)	C10'—C11'—H11B	120.0
C6—C5—C4	120.75 (18)	C12'—C11'—H11B	120.0
C6—C5—H5A	119.6	C11'—C12'—C13'	120.0
C4—C5—H5A	119.6	C11'—C12'—H12B	120.0
C7—C6—C5	117.89 (18)	C13'—C12'—H12B	120.0
C7—C6—H6A	121.1	C12'—C13'—C14'	120.0
C5—C6—H6A	121.1	C12'—C13'—C16'	117.3 (6)
C8—C7—F1	118.72 (19)	C14'—C13'—C16'	122.6 (6)
C8—C7—C6	123.13 (18)	C13'—C14'—C15'	120.0
F1—C7—C6	118.14 (19)	C13'—C14'—Cl1'	118.8 (4)
C7—C8—C9	118.77 (19)	C15'—C14'—Cl1'	121.0 (4)
C7—C8—H8A	120.6	C14'—C15'—C10'	120.0
C9—C8—H8A	120.6	C14'—C15'—H15B	120.0
C4—C9—C8	120.24 (19)	C10'—C15'—H15B	120.0
C4—C9—H9A	119.9	C13'—C16'—H16D	109.5
C8—C9—H9A	119.9	C13'—C16'—H16E	109.5
C11—C10—C15	120.0	H16D—C16'—H16E	109.5
C11—C10—N1	122.16 (19)	C13'—C16'—H16F	109.5
C15—C10—N1	117.83 (19)	H16D—C16'—H16F	109.5
C12—C11—C10	120.0	H16E—C16'—H16F	109.5

C10—N1—C1—O1	4.4 (3)	C3—N1—C10—C15	141.68 (18)
C3—N1—C1—O1	175.57 (17)	C10'—N1—C10—C15	6 (3)
C10'—N1—C1—O1	−7.7 (5)	C15—C10—C11—C12	0.0
C10—N1—C1—C2	−175.3 (2)	N1—C10—C11—C12	−178.9 (4)
C3—N1—C1—C2	−4.1 (2)	C10—C11—C12—C13	0.0
C10'—N1—C1—C2	172.6 (5)	C11—C12—C13—C14	0.0
O1—C1—C2—S1	−178.03 (15)	C11—C12—C13—C16	178.6 (2)
N1—C1—C2—S1	1.69 (19)	C12—C13—C14—C15	0.0
C3—S1—C2—C1	0.67 (13)	C16—C13—C14—C15	−178.6 (2)
C1—N1—C3—C4	126.12 (17)	C12—C13—C14—Cl1	−178.2 (2)
C10—N1—C3—C4	−62.0 (3)	C16—C13—C14—Cl1	3.2 (3)
C10'—N1—C3—C4	−50.3 (5)	C13—C14—C15—C10	0.0
C1—N1—C3—S1	4.38 (19)	Cl1—C14—C15—C10	178.24 (19)
C10—N1—C3—S1	176.3 (2)	C11—C10—C15—C14	0.0
C10'—N1—C3—S1	−172.0 (5)	N1—C10—C15—C14	178.9 (4)
C2—S1—C3—N1	−2.61 (13)	C1—N1—C10'—C11'	−42.6 (8)
C2—S1—C3—C4	−125.71 (13)	C10—N1—C10'—C11'	−176 (4)
N1—C3—C4—C9	127.67 (17)	C3—N1—C10'—C11'	133.9 (4)
S1—C3—C4—C9	−113.73 (16)	C1—N1—C10'—C15'	136.3 (4)
N1—C3—C4—C5	−52.9 (2)	C10—N1—C10'—C15'	3 (3)
S1—C3—C4—C5	65.75 (18)	C3—N1—C10'—C15'	−47.2 (8)
C9—C4—C5—C6	2.0 (3)	C15'—C10'—C11'—C12'	0.0
C3—C4—C5—C6	−177.47 (16)	N1—C10'—C11'—C12'	178.9 (10)
C4—C5—C6—C7	−0.2 (3)	C10'—C11'—C12'—C13'	0.0
C5—C6—C7—C8	−1.8 (3)	C11'—C12'—C13'—C14'	0.0
C5—C6—C7—F1	178.96 (16)	C11'—C12'—C13'—C16'	−176.3 (7)
F1—C7—C8—C9	−178.89 (17)	C12'—C13'—C14'—C15'	0.0
C6—C7—C8—C9	1.9 (3)	C16'—C13'—C14'—C15'	176.1 (7)
C5—C4—C9—C8	−1.9 (3)	C12'—C13'—C14'—Cl1'	175.6 (5)
C3—C4—C9—C8	177.55 (17)	C16'—C13'—C14'—Cl1'	−8.4 (7)
C7—C8—C9—C4	0.0 (3)	C13'—C14'—C15'—C10'	0.0
C1—N1—C10—C11	132.0 (2)	Cl1'—C14'—C15'—C10'	−175.5 (5)
C3—N1—C10—C11	−39.4 (3)	C11'—C10'—C15'—C14'	0.0
C10'—N1—C10—C11	−175 (3)	N1—C10'—C15'—C14'	−179.0 (10)
C1—N1—C10—C15	−46.9 (3)

Experimental details

Crystal data
Chemical formula	C₁₆H₁₃ClFNOS
M_r	321.78
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	113
a, b, c (Å)	12.265 (3), 12.994 (3), 18.192 (4)
V (Å³)	2899.3 (10)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.42
Crystal size (mm)	0.16 × 0.14 × 0.10

Data collection
Diffractometer	Rigaku Saturn
Absorption correction	Multi-scan (Jacobson, 1998)
T_min, T_max	0.937, 0.960
No. of measured, independent and observed [I > 2σ(I)] reflections	34208, 3445, 2796
R_int	0.056
(sin θ/λ)_max (Å⁻¹)	0.658

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.048, 0.125, 1.12
No. of reflections	3445
No. of parameters	240
No. of restraints	8
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.38, −0.76

Computer programs: CrystalClear (Rigaku/MSC, 2005), SHELXS97 (Sheldrick, 1990), SHELXL97 (Sheldrick, 1997), CrystalStructure (Rigaku/MSC, 2005).

Acknowledgements

This work was supported by Jiangsu Key Laboratory of Chemistry of Low-Dimensional Materials.

References

Jacobson, R. (1998). Private communication to the Rigaku Corporation. Google Scholar
Rigaku/MSC (2005). CrystalClear (Version 1.36) and CrystalStructure (Version 3.7.0). Rigaku/MSC, Tokyo, Japan. Google Scholar
Sheldrick, G. M. (1990). Acta Cryst. A46, 467–473. CrossRef CAS Web of Science IUCr Journals Google Scholar
Sheldrick, G. M. (1997). SHELXL97. University of Göttingen, Germany. Google Scholar
Tumul Srivastava, Haq, W. & Katti, S. B. (2002). Tetrahedron, 58, 7619–7624. Web of Science CrossRef Google Scholar