10-(1,2,2-Trichloro-vin-yl)-10H-pheno-thia-zine 5,5-dioxide.

The title compound, C(14)H(8)Cl(3)NO(2)S, forms a dimeric structure by inter-molecular Cl⋯O=S inter-actions. The dimers make a two-dimensional array parallel to (101) by other Cl⋯O=S inter-actions. The two-dimensional network is found to be kept unchanged, although the trichloro-vinyl 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. (2011 ▶); 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 = 360.64

Monoclinic,

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 F 2 > 2σ(F 2)

R int = 0.040

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.097

S = 1.07

3350 reflections

217 parameters

H-atom parameters constrained

Δρmax = 0.38 e Å−3

Δρmin = −0.34 e Å−3

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 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S160053681203245X/ff2076sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681203245X/ff2076Isup2.hkl

Supplementary material file. DOI: 10.1107/S160053681203245X/ff2076Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C14H8Cl3NO2S	F(000) = 728.00
Mr = 360.64	Dx = 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

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

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(Fo2) + (0.0468P)2 + 0.463P] where P = (Fo2 + 2Fc2)/3
3350 reflections	(Δ/σ)max < 0.001
217 parameters	Δρmax = 0.38 e Å−3
0 restraints	Δρmin = −0.34 e Å−3
Primary atom site location: structure-invariant direct methods

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).

	x	y	z	Uiso*/Ueq	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*

	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)

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)

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)

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 + , −y + , z − ; (ii) −x, −y, −z + 1; (iii) −x + , y − , −z + .