10-(1,2,2-Trichloro­vin­yl)-10H-pheno­thia­zine 5,5-dioxide

Tabata, H.; Okuno, T.

doi:10.1107/S160053681203245X

organic compounds

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ISSN: 2056-9890

Volume 68| Part 8| August 2012| Page o2519

https://doi.org/10.1107/S160053681203245X

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10-(1,2,2-Trichlorovinyl)-10H-phenothiazine 5,5-dioxide

Hideyuki Tabata ^a and Tsunehisa Okuno ^a ^*

^aDepartment of Material Science and Chemistry, Wakayama University, Sakaedani, Wakayama 640-8510, Japan
^*Correspondence e-mail: okuno@center.wakayama-u.ac.jp

(Received 9 July 2012; accepted 17 July 2012; online 21 July 2012)

The title compound, C₁₄H₈Cl₃NO₂S, forms a dimeric structure by intermolecular Cl⋯O=S interactions. The dimers make a two-dimensional array parallel to (101) by other Cl⋯O=S interactions. The two-dimensional network is found to be kept unchanged, although the trichlorovinyl group is disordered (relative occupancies 0.65:0.35).

Related literature

For related reviews of halogen bonding, see: Auffinger et al. (2004 ); Politzer et al. (2007 ). For related structures of phenothiazine 5,5-dioxide compounds, see: Harrison et al. (2007 ); Kamtekar et al. (2011 ); Siddegowda et al. (2011a ,b ); Zhu et al. (2007 ). For related structures with intermolecular Cl⋯O=S contacts, see: Bandera et al. (2007 ); Choi et al. (2008 ); Douglas et al. (1993 ); Jovanovic et al. (1986 ). For the preparation of the title compound, see: Okuno et al. (2006 ).

Experimental

Crystal data

C₁₄H₈Cl₃NO₂S
M_r = 360.64
Monoclinic, P 2₁ /n
a = 7.703 (3) Å
b = 12.766 (5) Å
c = 14.884 (6) Å
β = 93.028 (6)°
V = 1461.7 (10) Å³
Z = 4
Mo Kα radiation
μ = 0.77 mm⁻¹
T = 93 K
0.10 × 0.10 × 0.10 mm

Data collection

Rigaku Saturn724+ diffractometer
Absorption correction: numerical (NUMABS; Rigaku, 1999 ) T_min = 0.964, T_max = 0.970
11979 measured reflections
3350 independent reflections
2660 reflections with F² > 2σ(F²)
R_int = 0.040

Refinement

R[F² > 2σ(F²)] = 0.040
wR(F²) = 0.097
S = 1.07
3350 reflections
217 parameters
H-atom parameters constrained
Δρ_max = 0.38 e Å⁻³
Δρ_min = −0.34 e Å⁻³

Table 1
The geometry of intermolecular Cl⋯O=S contacts (Å, °)

Atoms	Cl⋯O	C—Cl⋯O	Cl⋯O=S
C13A—Cl1⋯O1ⁱ=S1	3.1571 (19)	167.60 (14)	101.82 (9)
C14B—Cl1⋯O1ⁱ=S1	3.1571 (19)	157.5 (3)	101.82 (9)
C14A—Cl2⋯O1ⁱⁱ=S1	3.0521 (19)	175.00 (15)	166.90 (10)
C13B—Cl2⋯O1ⁱⁱ=S1	3.0521 (19)	144.7 (3)	166.90 (10)
C14A—Cl3A⋯O2ⁱⁱⁱ=S1	3.174 (5)	157.7 (3)	100.61 (13)
C14B—Cl3B⋯O2ⁱⁱⁱ=S1	3.175 (9)	160.8 (5)	104.74 (18)
Symmetry codes: (i) x + $[{1\over 2}]$ , −y + $[{1\over 2}]$ , z − $[{1\over 2}]$ ; (ii) −x, −y, −z + 1; (iii) −x + $[{1\over 2}]$ , y − $[{1\over 2}]$ , −z + $[{1\over 2}]$ .

Data collection: CrystalClear (Rigaku, 2008 ); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997 ); software used to prepare material for publication: CrystalStructure (Rigaku, 2010 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S160053681203245X/ff2076sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S160053681203245X/ff2076Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S160053681203245X/ff2076Isup3.cml

checkCIF report

Comment top

Halogen bondings between halogen atoms and Lewis bases have been paid attention from the viewpoint of protein chemistry because of their use for the design of supramolecular assemblies (Auffinger et al. 2004; Politzer et al., 2007). However, Cl···O=S interactions in heterocycles such as thiophenes and phenothiazines have been reported only in two cases (Douglas et al., 1993; Jovanovic et al., 1986). This is the first report of Cl···O=S interactions in phenothiazine 5,5-dioxide compounds.

The trichlorovinyl group is disordered to give two orientations, which are represented by the form A (C13A/C14A/Cl3A) and the form B (C13B/C14B/Cl3B) (Figure 1). The occupancies of A and B are determined to 0.65 for A and 0.35 for B as both disordered forms have similar thermal parameters. Both trichlorovinyl groups have a planar structure (the N1/C13A/C14A/Cl1/Cl2/Cl3A plane: r.m.s. deviation = 0.0465 Å and the N1/C13B/C14B/Cl1/Cl2/Cl3B plane: r.m.s. deviation = 0.0521 Å). The structures around N1 are pyramidal in A and planar in B, where the distances of N1 to the C1/C12/C13A plane and the C1/C12/C13B plane are 0.212 (2) Å and 0.071 (2) Å, respectively.

The phenothiazine moiety has a butterfly structure, where the dihedral angle between two benzene rings (the C1—C6 plane: r.m.s. deviation = 0.0103 Å and the C7—C12 plane: r.m.s. deviation = 0.0114 Å) is 162.51 (9)°. The central six-membered ring (the N1/C1/C6/S1/C7/C12 ring) has a boat form. The length of the equatorial S1—O2 bond is in the range of the reported values (1.4293 (14) Å - 1.4421 (11) Å) of phenothiazine 5,5-dioxide compounds (Harrison et al., 2007; Kamtekar et al., 2011; Siddegowda et al., 2011a,b; Zhu et al., 2007), while the axial S1—O1 bond shows a longer bond length compared with that of the reported values (1.4294 (13) Å - 1.4495 (17) Å). This elongation may be caused by the intermolecular Cl···O=S interactions.

The molecules form a dimeric structure by the intermolecular Cl2ⁱⁱ···O1 interactions [Symmetry code: (ii) -x, -y, -z + 1]. The dimers make a two-dimensional array on the (101) plane by other Cl···O=S interactions (Figure 2). The intermolecular Cl···O=S distances are in the range of reported values (2.741 (3) Å - 3.267 (2) Å (Bandera et al., 2007; Choi et al., 2008)). Remarkable contacts cannot be observed between the arrays. The two-dimensional network is found to be kept unchanged, although the trichlorovinyl group is disordered.

Related literature top

For related reviews of halogen bonding, see: Auffinger et al. (2004); Politzer et al. (2007). For related structures of phenothiazine 5,5-dioxide compounds, see: Harrison et al. (2007); Kamtekar et al. (2011); Siddegowda et al. (2011a,b); Zhu et al. (2007). For related structures with intermolecular Cl···O=S contacts, see: Bandera et al. (2007); Choi et al. (2008); Douglas et al. (1993); Jovanovic et al. (1986). For the preparation of the title compound, see: Okuno et al. (2006).

Experimental top

The title compound was prepared according to a reported procedure (Okuno et al., 2006). The single crystals with sufficient quality for X-ray analysis were obtained by concentration of a dichloromethane solution.

Structure description top

For related reviews of halogen bonding, see: Auffinger et al. (2004); Politzer et al. (2007). For related structures of phenothiazine 5,5-dioxide compounds, see: Harrison et al. (2007); Kamtekar et al. (2011); Siddegowda et al. (2011a,b); Zhu et al. (2007). For related structures with intermolecular Cl···O=S contacts, see: Bandera et al. (2007); Choi et al. (2008); Douglas et al. (1993); Jovanovic et al. (1986). For the preparation of the title compound, see: Okuno et al. (2006).

Computing details top

Data collection: CrystalClear (Rigaku, 2008); cell refinement: CrystalClear (Rigaku, 2008); data reduction: CrystalClear (Rigaku, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: CrystalStructure (Rigaku, 2010).

Figures top

	Fig. 1. The asymmetric unit of the title compound with atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level and H atoms are shown as small spheres. Disordered atoms are discriminated with A/B notation, and the minor disordered form is drawn as open bonds.
	Fig. 2. A view of the two-dimensional array on the (101) plane. Hydrogen atoms are omitted for clarity. The Cl···O=S interactions are shown as dashed lines. [Symmetry codes: (i) x + 1/2, -y + 1/2, z - 1/2; (ii) -x, -y, -z + 1; (iii) -x + 1/2, y - 1/2, -z + 1/2].

10-(1,2,2-Trichlorovinyl)-10H-phenothiazine 5,5-dioxide top

Crystal data top

C₁₄H₈Cl₃NO₂S	F(000) = 728.00
M_r = 360.64	D_x = 1.639 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71075 Å
Hall symbol: -P 2yn	Cell parameters from 4473 reflections
a = 7.703 (3) Å	θ = 2.1–31.1°
b = 12.766 (5) Å	µ = 0.77 mm⁻¹
c = 14.884 (6) Å	T = 93 K
β = 93.028 (6)°	Block, colourless
V = 1461.7 (10) Å³	0.10 × 0.10 × 0.10 mm
Z = 4

Data collection top

Rigaku Saturn724+ diffractometer	2660 reflections with F² > 2σ(F²)
Detector resolution: 7.111 pixels mm^-1	R_int = 0.040
ω scans	θ_max = 27.5°
Absorption correction: numerical (NUMABS; Rigaku, 1999)	h = −9→9
T_min = 0.964, T_max = 0.970	k = −16→16
11979 measured reflections	l = −16→19
3350 independent reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.097	H-atom parameters constrained
S = 1.07	w = 1/[σ²(F_o²) + (0.0468P)² + 0.463P] where P = (F_o² + 2F_c²)/3
3350 reflections	(Δ/σ)_max < 0.001
217 parameters	Δρ_max = 0.38 e Å⁻³
0 restraints	Δρ_min = −0.34 e Å⁻³
Primary atom site location: structure-invariant direct methods

Crystal data top

C₁₄H₈Cl₃NO₂S	V = 1461.7 (10) Å³
M_r = 360.64	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 7.703 (3) Å	µ = 0.77 mm⁻¹
b = 12.766 (5) Å	T = 93 K
c = 14.884 (6) Å	0.10 × 0.10 × 0.10 mm
β = 93.028 (6)°

Data collection top

Rigaku Saturn724+ diffractometer	3350 independent reflections
Absorption correction: numerical (NUMABS; Rigaku, 1999)	2660 reflections with F² > 2σ(F²)
T_min = 0.964, T_max = 0.970	R_int = 0.040
11979 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.040	0 restraints
wR(F²) = 0.097	H-atom parameters constrained
S = 1.07	Δρ_max = 0.38 e Å⁻³
3350 reflections	Δρ_min = −0.34 e Å⁻³
217 parameters

Special details top

Refinement. Refinement was performed using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F². R-factor (gt) are based on F. The threshold expression of F² > 2.0 σ(F²) is used only for calculating R-factor (gt).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
Cl1	0.35886 (7)	0.18970 (5)	0.16632 (4)	0.02359 (15)
Cl2	0.04748 (7)	−0.04673 (5)	0.28388 (4)	0.02550 (15)
Cl3A	0.1475 (6)	−0.0132 (4)	0.1010 (4)	0.0266 (6)	0.6500
Cl3B	0.1789 (11)	0.0075 (6)	0.0902 (6)	0.0245 (10)	0.3500
S1	0.22085 (7)	0.24593 (4)	0.51836 (3)	0.01767 (14)
O1	0.1318 (2)	0.16939 (13)	0.57137 (11)	0.0228 (4)
O2	0.2795 (2)	0.33968 (13)	0.56464 (11)	0.0249 (4)
N1	0.2211 (3)	0.14499 (17)	0.33098 (13)	0.0280 (5)
C1	0.3743 (3)	0.13499 (18)	0.38622 (15)	0.0215 (5)
C2	0.5134 (3)	0.0742 (2)	0.35768 (16)	0.0280 (6)
C3	0.6655 (3)	0.0672 (2)	0.40926 (17)	0.0284 (6)
C4	0.6877 (3)	0.1205 (3)	0.49020 (17)	0.0292 (6)
C5	0.5510 (3)	0.1783 (2)	0.52011 (17)	0.0278 (6)
C6	0.3943 (3)	0.18481 (18)	0.46904 (14)	0.0188 (5)
C7	0.0856 (3)	0.27768 (18)	0.42469 (14)	0.0177 (5)
C8	−0.0368 (3)	0.35745 (19)	0.43520 (15)	0.0226 (5)
C9	−0.1597 (4)	0.3786 (2)	0.36668 (16)	0.0277 (6)
C10	−0.1595 (4)	0.3195 (3)	0.28853 (16)	0.0303 (6)
C11	−0.0370 (3)	0.2424 (3)	0.27715 (16)	0.0296 (6)
C12	0.0911 (3)	0.22094 (19)	0.34472 (15)	0.0220 (5)
C13A	0.2397 (5)	0.1139 (3)	0.2389 (3)	0.0173 (7)	0.6500
C13B	0.1713 (9)	0.0641 (6)	0.2626 (5)	0.0179 (13)	0.3500
C14A	0.1559 (5)	0.0287 (3)	0.2101 (3)	0.0195 (7)	0.6500
C14B	0.2264 (9)	0.0852 (6)	0.1815 (6)	0.0189 (13)	0.3500
H1	0.5017	0.0377	0.3021	0.0336*
H2	0.7574	0.0250	0.3892	0.0341*
H3	0.7952	0.1173	0.5244	0.0351*
H4	0.5636	0.2141	0.5760	0.0334*
H5	−0.0352	0.3969	0.4894	0.0272*
H6	−0.2428	0.4327	0.3730	0.0332*
H7	−0.2457	0.3323	0.2418	0.0363*
H8	−0.0397	0.2034	0.2227	0.0355*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0269 (3)	0.0239 (3)	0.0204 (3)	−0.0051 (3)	0.0049 (3)	0.0012 (3)
Cl2	0.0266 (3)	0.0235 (3)	0.0266 (3)	−0.0077 (3)	0.0025 (3)	0.0016 (3)
Cl3A	0.0265 (14)	0.0306 (15)	0.0225 (12)	0.0019 (9)	−0.0008 (9)	−0.0111 (10)
Cl3B	0.027 (3)	0.030 (3)	0.0172 (18)	−0.0011 (15)	0.0001 (15)	−0.0085 (16)
S1	0.0181 (3)	0.0219 (3)	0.0130 (3)	0.0017 (2)	−0.0001 (2)	−0.0001 (2)
O1	0.0223 (8)	0.0271 (9)	0.0195 (8)	0.0016 (7)	0.0046 (7)	0.0054 (7)
O2	0.0280 (9)	0.0260 (9)	0.0203 (9)	0.0004 (7)	−0.0038 (7)	−0.0062 (7)
N1	0.0294 (11)	0.0345 (12)	0.0189 (10)	0.0166 (10)	−0.0087 (9)	−0.0110 (9)
C1	0.0207 (12)	0.0249 (12)	0.0186 (11)	0.0061 (10)	−0.0016 (9)	0.0001 (10)
C2	0.0289 (13)	0.0355 (15)	0.0196 (12)	0.0152 (12)	0.0007 (10)	−0.0018 (11)
C3	0.0245 (13)	0.0330 (14)	0.0280 (13)	0.0108 (11)	0.0045 (11)	0.0066 (11)
C4	0.0171 (12)	0.0405 (16)	0.0297 (14)	0.0038 (11)	−0.0028 (10)	0.0041 (12)
C5	0.0207 (12)	0.0398 (16)	0.0226 (12)	−0.0012 (11)	−0.0019 (10)	−0.0028 (11)
C6	0.0177 (11)	0.0219 (12)	0.0166 (11)	0.0006 (9)	0.0009 (9)	0.0020 (9)
C7	0.0175 (11)	0.0223 (12)	0.0132 (10)	0.0006 (9)	0.0012 (9)	0.0014 (9)
C8	0.0257 (12)	0.0244 (12)	0.0181 (11)	0.0054 (10)	0.0043 (10)	−0.0009 (9)
C9	0.0273 (13)	0.0331 (14)	0.0227 (12)	0.0148 (11)	0.0006 (10)	0.0004 (11)
C10	0.0280 (13)	0.0413 (16)	0.0210 (12)	0.0129 (12)	−0.0047 (11)	−0.0012 (11)
C11	0.0278 (13)	0.0416 (16)	0.0187 (12)	0.0138 (12)	−0.0049 (10)	−0.0056 (11)
C12	0.0237 (12)	0.0251 (12)	0.0168 (11)	0.0077 (10)	−0.0020 (9)	−0.0016 (9)
C13A	0.0180 (18)	0.0191 (19)	0.0148 (19)	0.0027 (16)	0.0002 (15)	0.0002 (17)
C13B	0.016 (4)	0.012 (3)	0.026 (4)	0.000 (3)	0.002 (3)	0.002 (4)
C14A	0.0204 (19)	0.021 (2)	0.0177 (19)	0.0048 (16)	0.0016 (15)	−0.0027 (17)
C14B	0.016 (4)	0.013 (3)	0.027 (4)	0.001 (3)	−0.002 (3)	−0.001 (3)

Geometric parameters (Å, º) top

Cl1—C13A	1.747 (4)	C4—C5	1.379 (4)
Cl1—C14B	1.703 (7)	C5—C6	1.394 (3)
Cl2—C13B	1.745 (8)	C7—C8	1.402 (4)
Cl2—C14A	1.711 (4)	C7—C12	1.396 (4)
Cl3A—C14A	1.707 (7)	C8—C9	1.381 (4)
Cl3B—C14B	1.707 (11)	C9—C10	1.387 (4)
S1—O1	1.4509 (18)	C10—C11	1.380 (4)
S1—O2	1.4415 (18)	C11—C12	1.399 (4)
S1—C6	1.743 (3)	C13A—C14A	1.324 (6)
S1—C7	1.743 (3)	C13B—C14B	1.328 (11)
N1—C1	1.408 (3)	C2—H1	0.950
N1—C12	1.416 (4)	C3—H2	0.950
N1—C13A	1.441 (5)	C4—H3	0.950
N1—C13B	1.485 (8)	C5—H4	0.950
C1—C2	1.407 (4)	C8—H5	0.950
C1—C6	1.388 (4)	C9—H6	0.950
C2—C3	1.369 (4)	C10—H7	0.950
C3—C4	1.387 (4)	C11—H8	0.950

O1—S1—O2	116.39 (10)	C7—C12—C11	117.3 (3)
O1—S1—C6	108.83 (11)	Cl1—C13A—N1	121.1 (3)
O1—S1—C7	108.16 (11)	Cl1—C13A—C14A	121.2 (4)
O2—S1—C6	110.19 (11)	N1—C13A—C14A	117.6 (4)
O2—S1—C7	110.36 (11)	Cl2—C13B—N1	124.3 (5)
C6—S1—C7	101.91 (11)	Cl2—C13B—C14B	122.2 (6)
C1—N1—C12	123.7 (2)	N1—C13B—C14B	113.5 (6)
C1—N1—C13A	114.1 (3)	Cl2—C14A—Cl3A	116.0 (3)
C1—N1—C13B	121.0 (4)	Cl2—C14A—C13A	120.1 (4)
C12—N1—C13A	115.6 (3)	Cl3A—C14A—C13A	123.9 (4)
C12—N1—C13B	114.6 (3)	Cl1—C14B—Cl3B	117.0 (6)
N1—C1—C2	120.1 (2)	Cl1—C14B—C13B	120.1 (6)
N1—C1—C6	121.8 (2)	Cl3B—C14B—C13B	122.8 (7)
C2—C1—C6	118.0 (2)	C1—C2—H1	119.668
C1—C2—C3	120.7 (3)	C3—C2—H1	119.665
C2—C3—C4	121.1 (3)	C2—C3—H2	119.434
C3—C4—C5	118.8 (3)	C4—C3—H2	119.419
C4—C5—C6	120.6 (3)	C3—C4—H3	120.585
S1—C6—C1	121.81 (17)	C5—C4—H3	120.590
S1—C6—C5	117.24 (18)	C4—C5—H4	119.689
C1—C6—C5	120.6 (2)	C6—C5—H4	119.683
S1—C7—C8	117.16 (17)	C7—C8—H5	120.053
S1—C7—C12	121.16 (18)	C9—C8—H5	120.047
C8—C7—C12	121.5 (2)	C8—C9—H6	120.592
C7—C8—C9	119.9 (3)	C10—C9—H6	120.585
C8—C9—C10	118.8 (3)	C9—C10—H7	119.271
C9—C10—C11	121.5 (3)	C11—C10—H7	119.270
C10—C11—C12	120.8 (3)	C10—C11—H8	119.575
N1—C12—C7	122.1 (2)	C12—C11—H8	119.581
N1—C12—C11	120.5 (2)

O1—S1—C6—C1	87.90 (18)	C13B—N1—C12—C11	−24.3 (5)
O1—S1—C6—C5	−85.66 (17)	N1—C1—C2—C3	177.5 (2)
O1—S1—C7—C8	86.33 (17)	N1—C1—C6—S1	10.3 (4)
O1—S1—C7—C12	−89.26 (17)	N1—C1—C6—C5	−176.39 (19)
O2—S1—C6—C1	−143.36 (16)	C2—C1—C6—S1	−170.48 (19)
O2—S1—C6—C5	43.07 (18)	C2—C1—C6—C5	2.9 (4)
O2—S1—C7—C8	−42.04 (18)	C6—C1—C2—C3	−1.8 (4)
O2—S1—C7—C12	142.37 (15)	C1—C2—C3—C4	−0.9 (4)
C6—S1—C7—C8	−159.07 (15)	C2—C3—C4—C5	2.4 (4)
C6—S1—C7—C12	25.34 (19)	C3—C4—C5—C6	−1.3 (4)
C7—S1—C6—C1	−26.21 (19)	C4—C5—C6—S1	172.3 (2)
C7—S1—C6—C5	160.23 (15)	C4—C5—C6—C1	−1.4 (4)
C1—N1—C12—C7	−14.0 (4)	S1—C7—C8—C9	−173.12 (15)
C1—N1—C12—C11	165.5 (2)	S1—C7—C12—N1	−8.8 (3)
C12—N1—C1—C2	−166.01 (19)	S1—C7—C12—C11	171.66 (14)
C12—N1—C1—C6	13.2 (4)	C8—C7—C12—N1	175.7 (2)
C1—N1—C13A—Cl1	−71.3 (4)	C8—C7—C12—C11	−3.7 (4)
C1—N1—C13A—C14A	112.1 (3)	C12—C7—C8—C9	2.5 (4)
C13A—N1—C1—C2	−15.9 (4)	C7—C8—C9—C10	0.3 (4)
C13A—N1—C1—C6	163.4 (3)	C8—C9—C10—C11	−1.7 (4)
C1—N1—C13B—Cl2	88.4 (6)	C9—C10—C11—C12	0.4 (4)
C1—N1—C13B—C14B	−93.3 (5)	C10—C11—C12—N1	−177.2 (3)
C13B—N1—C1—C2	24.4 (5)	C10—C11—C12—C7	2.3 (4)
C13B—N1—C1—C6	−156.4 (4)	Cl1—C13A—C14A—Cl2	177.4 (2)
C12—N1—C13A—Cl1	81.4 (3)	Cl1—C13A—C14A—Cl3A	−2.6 (5)
C12—N1—C13A—C14A	−95.2 (4)	N1—C13A—C14A—Cl2	−6.0 (5)
C13A—N1—C12—C7	−163.7 (3)	N1—C13A—C14A—Cl3A	174.0 (3)
C13A—N1—C12—C11	15.8 (4)	Cl2—C13B—C14B—Cl1	−175.6 (4)
C12—N1—C13B—Cl2	−82.2 (6)	Cl2—C13B—C14B—Cl3B	1.1 (9)
C12—N1—C13B—C14B	96.1 (5)	N1—C13B—C14B—Cl1	6.0 (8)
C13B—N1—C12—C7	156.3 (4)	N1—C13B—C14B—Cl3B	−177.2 (4)

Experimental details

Crystal data
Chemical formula	C₁₄H₈Cl₃NO₂S
M_r	360.64
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	93
a, b, c (Å)	7.703 (3), 12.766 (5), 14.884 (6)
β (°)	93.028 (6)
V (Å³)	1461.7 (10)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.77
Crystal size (mm)	0.10 × 0.10 × 0.10

Data collection
Diffractometer	Rigaku Saturn724+
Absorption correction	Numerical (NUMABS; Rigaku, 1999)
T_min, T_max	0.964, 0.970
No. of measured, independent and observed [F² > 2σ(F²)] reflections	11979, 3350, 2660
R_int	0.040
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.040, 0.097, 1.07
No. of reflections	3350
No. of parameters	217
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.38, −0.34

Computer programs: CrystalClear (Rigaku, 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), CrystalStructure (Rigaku, 2010).

The geometry of intermolecular Cl···O=S contacts (Å, °). top

Atoms	Cl···O	C-Cl···O	Cl···O=S
C13A-Cl1···O1ⁱ=S1	3.1571 (19)	167.60 (14)	101.82 (9)
C14B-Cl1···O1ⁱ=S1	3.1571 (19)	157.5 (3)	101.82 (9)
C14A-Cl2···O1ⁱⁱ=S1	3.0521 (19)	175.00 (15)	166.90 (10)
C13B-Cl2···O1ⁱⁱ=S1	3.0521 (19)	144.7 (3)	166.90 (10)
C14A-Cl3A···O2ⁱⁱⁱ=S1	3.174 (5)	157.7 (3)	100.61 (13)
C14B-Cl3B···O2ⁱⁱⁱ=S1	3.175 (9)	160.8 (5)	104.74 (18)

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

Acknowledgements

This work was supported by Research for Promoting Technological Seeds from the Japan Science and Technology Agency (JST).

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