Crystal structures of isomeric 3,5-di-chloro-N-(2,3-di-methyl-phen-yl)benzene-sulfonamide, 3,5-di-chloro-N-(2,6-di-methyl-phen-yl)benzene-sulfonamide and 3,5-di-chloro-N-(3,5-di-methyl-phen-yl)benzene-sulfonamide.

The crystal structures of three isomeric compounds of formula C14H13Cl2NO2S, namely 3,5-di-chloro-N-(2,3-di-methyl-phen-yl)-benzene-sulfonamide (I), 3,5-di-chloro-N-(2,6-di-methyl-phen-yl)benzene-sulfonamide (II) and 3,5-di-chloro-N-(3,5-di-methyl-phen-yl)benzene-sulfonamide (III) are described. The mol-ecules of all the three compounds are U-shaped with the two aromatic rings inclined at 41.3 (6)° in (I), 42.1 (2)° in (II) and 54.4 (3)° in (III). The mol-ecular conformation of (II) is stabilized by intra-molecular C-H⋯O hydrogen bonds and C-H⋯π inter-actions. The crystal structure of (I) features N-H⋯O hydrogen-bonded R22(8) loops inter-connected via C(7) chains of C-H⋯O inter-actions, forming a three-dimensional architecture. The structure also features π-π inter-actions [Cg⋯Cg = 3.6970 (14) Å]. In (II), N-H⋯O hydrogen-bonded R22(8) loops are inter-connected via π-π inter-actions [inter-centroid distance = 3.606 (3) Å] to form a one-dimensional architecture running parallel to the a axis. In (III), adjacent C(4) chains of N-H⋯O hydrogen-bonded mol-ecules running parallel to [010] are connected via C-H⋯π inter-actions, forming sheets parallel to the ab plane. Neighbouring sheets are linked via offset π-π inter-actions [inter-centroid distance = 3.8303 (16) Å] to form a three-dimensional architecture.

Chemical context

Sulfonamide drugs were the first chemotherapeutic agents to be used for curing and preventing bacterial infection in human beings (Shiva Prasad et al., 2011 ▸). They play a vital role as key constituents in a number of biologically active mol­ecules and are known to exhibit a wide variety of biological activities, such as anti­bacterial (Subhakara Reddy et al., 2012 ▸; Himel et al., 1971 ▸), anti­fungal (Hanafy et al., 2007 ▸), anti-inflammatory (Küçükgüzel et al., 2013 ▸), anti­tumor (Ghorab et al., 2011 ▸), anti­cancer (Al-Said et al., 2011 ▸), anti-HIV (Sahu et al., 2007 ▸) and anti­tubercular activities (Vora & Mehta, 2012 ▸). In recent years, extensive research studies have been carried out on the synthesis and evaluation of the pharmacological properties of mol­ecules containing the sulfonamide moiety, which have been reported to be important pharmacophores (Mohan et al., 2013 ▸).

With these considerations in mind and based on our structural study of 3,5-di­chloro-N-(substitutedphen­yl)benzene­sulfonamides (Shakuntala, Naveen et al., 2017 ▸; Shakuntala, Lokanath et al., 2017 ▸), we report herein the crystal structures of three isomers, viz. 3,5-di­chloro-N-(2,3-di­methyl­phen­yl)-benzene­sulfonamide (I), 3,5-di­chloro-N-(2,6-di­methyl­phen­yl)benzene­sulfonamide (II) and 3,5-di­chloro-N-(3,5-di­methyl­phen­yl)benzene­sulfonamide (III).

Structural commentary

The mol­ecule of (I) (Fig. 1 ▸) is U-shaped, with the sulfonyl­benzene ring and the aniline ring inclined by 41.3 (6)°. The N—C bond in the C–SO2–NH–C segment has a gauche torsion with respect to the S=O bonds, and the mol­ecule is twisted at the S—N bond, with a C1—S1—N1—C7 torsion angle of 60.9 (2)°.

Figure 1

The mol­ecular structure of (I) with displacement ellipsoids drawn at the 50% probability level.

In the U-shaped mol­ecules of (II) (Fig. 2 ▸), the dihedral angle between the sulfonyl­benzene ring and the aniline ring is 42.1 (2)°. The mol­ecule is twisted at the S—N bond, with a C1—S1—N1—C7 torsion angle of 69.8 (3)°. The mol­ecular conformation of (II) is stabilized by an intra­molecular C—H⋯O hydrogen bond and a C—H⋯π inter­action (Table 2 ▸). The N—C bond in the C–SO2–NH–C segment has a gauche torsion with respect to the S=O bonds.

Figure 2

The mol­ecular structure of (II) with displacement ellipsoids drawn at the 50% probability level. Intra­molecular C—H⋯O and C—H⋯π hydrogen inter­actions are shown as dotted lines.

Table 2

Hydrogen-bond geometry (Å, °) for (II)

Cg1 is the centroid of the C1–C6 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C14—H14C⋯O1	0.98	2.53	3.139 (8)	120
N1—H1⋯O2i	0.85 (4)	2.12 (4)	2.937 (5)	160 (4)
C13—H13A⋯Cg1	0.98	2.67	3.493 (5)	142

Symmetry code: (i) .

The mol­ecule of (III) (Fig. 3 ▸) is also U-shaped, with the sulfonyl­benzene ring tilted at an angle of 54.4 (3)° with respect to the aniline ring. The N—C bond in the C–SO2–NH–C segment has a gauche torsion with respect to the S=O bonds, and the mol­ecule is twisted at the S—N bond, with a C1—S1—N1—C7 torsion angle of 71.3 (2)°.

Figure 3

The mol­ecular structure of (III) with displacement ellipsoids drawn at the 50% probability level.

Supra­molecular features

The crystal structure of (I) features inversion-related dimers linked by N1—H1⋯O2i hydrogen bonds forming (8) loops (Fig. 4 ▸, Table 1 ▸). The (8) loops are inter­connected via C(7) chains of C4—H4⋯O1ii inter­molecular inter­actions, forming a three-dimensional supra­molecular architecture. The structure also features π–π inter­actions involving the benzene­sulfonyl ring and the aniline ring as illustrated in Fig. 4 ▸ [Cg1⋯Cg2iii = 3.6970 (14) Å; Cg1 and Cg2 are the centroids of the C1–C6 and C7–C12 rings, respectively; symmetry code: (iii)  − x, − + y,  − z].

Figure 4

The three-dimensional supra­molecular architecture of (I) viewed along the c axis. The N—H⋯O and C—H⋯O hydrogen bonds and π–π inter­actions are shown as thin blue dotted lines. H atoms not involved in hydrogen bonding are omitted for clarity.

Table 1

Hydrogen-bond geometry (Å, °) for (I)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O2i	0.86	2.14	2.9590	159
C4—H4⋯O1ii	0.95	2.41	3.332 (3)	164

Symmetry codes: (i) ; (ii) .

In (II), N1—H1⋯O2i hydrogen-bonded (8) loops (Fig. 5 ▸, Table 2 ▸) are connected via π–π inter­actions involving inversion-related benzene­sulfonyl rings, forming a one-dimensional architecture running parallel to the a axis, as shown in Fig. 5 ▸ [Cg1⋯Cg1ii = 3.606 (3) Å; Cg1 is the centroid of the C1–C6 ring; symmetry code: (ii) 2 − x, 1 − y, −z].

Figure 5

Partial crystal packing of (II) showing the formation of a one-dimensional architecture through N—H⋯O hydrogen bonds and π–π inter­actions (thin blue dotted lines).

In the crystal structure of (III), the mol­ecules are inter­linked via N1—H1⋯O1i hydrogen bonds (Fig. 6 ▸, Table 3 ▸) to form C(4) chains running parallel to [010]. Adjacent chains are connected by C14—H14B⋯π inter­actions involving the aniline ring, forming two-dimensional sheets parallel to the ab plane. Neighbouring sheets are further linked via offset π–π inter­actions involving inversion-related benzene­sulfonyl rings, forming a three dimensional architecture as as illustrated in Fig. 7 ▸ [Cg1⋯Cg1i = 3.8303 (16) Å, inter­planar distance = 3.3874 (11) Å, slippage 1.788 (3) Å; Cg1 is the centroid of the C1–C6 ring; symmetry code: (iii) 1 − x, −y, −z].

Figure 6

Partial crystal packing of (III) viewed down the c axis displaying two-dimensional sheets. Thin blue dotted lines denote N—H⋯O hydrogen bonds and C—H⋯π inter­actions. H atoms not involved in hydrogen bonding are omitted for clarity.

Table 3

Hydrogen-bond geometry (Å, °) for (III)

Cg2 is the centroid of the aniline ring C7–C12

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1i	0.87	2.13	2.9848	167
C14—H14B⋯Cg2ii	0.98	2.86	3.5135	124

Symmetry codes: (i) ; (ii) .

Figure 7

Crystal packing of (III) viewed approximately along the a axis, showing the π–π inter­actions (black dotted lines) between adjacent sheets. For clarity, only H atoms involved in N—H⋯O hydrogen bonds and C—H⋯π inter­actions (thin blue dotted lines) are included.

Database survey

Two 3,5-di­chloro-N-(substitutedphen­yl)-benzene­sulfon­amides, namely 3,5-di­chloro-N-(4-methyl­phen­yl)benzene­sulfonamide [Shakuntala, Naveen et al., 2017 ▸, (IV)] and 3,5-di­chloro-N-(2,4-di­chloro­phen­yl)benzene­sulfonamide [Shak­untala, Lokanath et al., 2017 ▸, (V)], have been reported previously. The mol­ecules of both (IV) and (V) are U-shaped with the central C–S–N–C segment having a torsion angle of 67.2 (4)° in (IV) and 58.7 (3)° in (V). The dihedral angle between the benzene rings is 57.0 (2)° in (IV) and 40.23 (2)° in (V). The crystal structure of (IV) displays a three-dimensional supra­molecular structure constructed via N—H⋯O and C—H⋯O hydrogen bonds and C—H⋯π inter­actions, whereas in (V) the three-dimensional supra­molecular architecture is built through N—H⋯O and C—H⋯O hydrogen bonds, Cl⋯Cl contacts and π–π inter­actions.

Synthesis and crystallization

The title compounds were prepared according to a literature method (Rodrigues et al., 2015 ▸). The purities of all the compounds were checked by determining their melting points. Colourless prismatic single crystals suitable for X-ray diffraction studies were obtained by slow evaporation of ethano­lic solutions of the compounds at room temperature.

Refinement details

Crystal data, data collection and structure refinement details are summarized in Table 4 ▸. The amino H atoms were located in difference-Fourier maps and refined isotropically with the N—H bond length restrained to be 0.88 (2) Å. All other H atoms were positioned geometrically and refined as riding with C—H = 0.95–0.98 Å and U iso(H) = 1.2 or 1.5U eq(C). A rotating model was applied to the methyl groups. To improve considerably the values of R1, wR2, and S (goodness-of-fit), a low-angle reflection partially obscured by the beam-stop (100) was omitted from the final refinement of (III).

Table 4

Experimental details

	(I)	(II)	(III)
Crystal data
Chemical formula	C14H13Cl2NO2S	C14H13Cl2NO2S	C14H13Cl2NO2S
M r	330.21	330.21	330.21
Crystal system, space group	Monoclinic, P21/n	Triclinic, P	Monoclinic, P21/c
Temperature (K)	100	100	100
a, b, c (Å)	8.2223 (3), 14.1546 (5), 12.7933 (4)	8.4817 (15), 8.6149 (15), 12.167 (2)	12.2268 (6), 7.0399 (3), 17.3130 (8)
α, β, γ (°)	90, 91.188 (1), 90	109.875 (5), 91.900 (5), 114.190 (5)	90, 100.409 (1), 90
V (Å3)	1488.61 (9)	747.1 (2)	1465.70 (12)
Z	4	2	4
Radiation type	Cu Kα	Cu Kα	Cu Kα
μ (mm−1)	5.24	5.22	5.32
Crystal size (mm)	0.28 × 0.25 × 0.22	0.29 × 0.26 × 0.22	0.27 × 0.24 × 0.21
Data collection
Diffractometer	Bruker APEXII CCD area detector	Bruker APEXII CCD area detector	Bruker APEXII CCD area detector
Absorption correction	Multi-scan (SADABS; Bruker, 2009 ▸)	Multi-scan (SADABS; Bruker, 2009 ▸)	Multi-scan (SADABS; Bruker,2009 ▸)
T min, T max	0.288, 0.316	0.275, 0.317	0.297, 0.327
No. of measured, independent and observed [I > 2σ(I)] reflections	10308, 2440, 2347	6977, 2400, 1960	11468, 2412, 2374
R int	0.053	0.124	0.056
(sin θ/λ)max (Å−1)	0.584	0.581	0.585
Refinement
R[F 2 > 2σ(F 2)], wR(F 2), S	0.057, 0.162, 1.07	0.074, 0.233, 1.02	0.058, 0.152, 0.99
No. of reflections	2440	2400	2412
No. of parameters	187	187	187
No. of restraints	1	1	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement	H atoms treated by a mixture of independent and constrained refinement	H atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3)	0.64, −0.63	0.99, −0.60	0.82, −0.88

Computer programs: APEX2, SAINT-Plus and XPREP (Bruker, 2009 ▸), SHELXT 2016/4 (Sheldrick, 2015a ▸), SHELXL2016/4 (Sheldrick, 2015b ▸) and Mercury (Macrae et al., 2008 ▸).

Crystal structure: contains datablock(s) I, II, III, shelx. DOI: 10.1107/S2056989017005230/rz5211sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989017005230/rz5211Isup2.hkl

Structure factors: contains datablock(s) II. DOI: 10.1107/S2056989017005230/rz5211IIsup3.hkl

Structure factors: contains datablock(s) III. DOI: 10.1107/S2056989017005230/rz5211IIIsup4.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S2056989017005230/rz5211Isup5.cml

Click here for additional data file.

Supporting information file. DOI: 10.1107/S2056989017005230/rz5211IIsup6.cml

Click here for additional data file.

Supporting information file. DOI: 10.1107/S2056989017005230/rz5211IIIsup7.cml

CCDC references: 1542706, 1542704, 1542705

Additional supporting information: crystallographic information; 3D view; checkCIF report

C14H13Cl2NO2S	Prism
Mr = 330.21	Dx = 1.473 Mg m−3
Monoclinic, P21/n	Melting point: 431 K
Hall symbol: -P 2yn	Cu Kα radiation, λ = 1.54178 Å
a = 8.2223 (3) Å	Cell parameters from 144 reflections
b = 14.1546 (5) Å	θ = 6.2–64.2°
c = 12.7933 (4) Å	µ = 5.24 mm−1
β = 91.188 (1)°	T = 100 K
V = 1488.61 (9) Å3	Prism, colourless
Z = 4	0.28 × 0.25 × 0.22 mm
F(000) = 680

Bruker APEXII CCD area detector diffractometer	2440 independent reflections
Radiation source: fine-focus sealed tube	2347 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.053
phi and φ scans	θmax = 64.2°, θmin = 6.2°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −9→9
Tmin = 0.288, Tmax = 0.316	k = −16→15
10308 measured reflections	l = −14→12

Refinement on F2	1 restraint
Least-squares matrix: full	Hydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.057	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.162	w = 1/[σ2(Fo2) + (0.1235P)2 + 0.7281P] where P = (Fo2 + 2Fc2)/3
S = 1.07	(Δ/σ)max < 0.001
2440 reflections	Δρmax = 0.64 e Å−3
187 parameters	Δρmin = −0.63 e Å−3

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.

	x	y	z	Uiso*/Ueq
C1	0.6064 (3)	0.35091 (16)	0.66816 (18)	0.0170 (5)
C2	0.7069 (3)	0.32517 (16)	0.75161 (18)	0.0189 (5)
H2	0.821571	0.332433	0.748662	0.023*
C3	0.6346 (3)	0.28862 (18)	0.83908 (19)	0.0222 (6)
C4	0.4689 (3)	0.27523 (17)	0.84477 (19)	0.0230 (6)
H4	0.421903	0.248689	0.905281	0.028*
C5	0.3733 (3)	0.30179 (17)	0.7592 (2)	0.0214 (6)
C6	0.4380 (3)	0.34137 (16)	0.67041 (19)	0.0191 (5)
H6	0.370447	0.361192	0.613395	0.023*
C7	0.8409 (3)	0.53406 (16)	0.67541 (19)	0.0200 (5)
C8	0.7774 (3)	0.56423 (17)	0.7703 (2)	0.0214 (6)
C9	0.8878 (3)	0.58319 (17)	0.8534 (2)	0.0255 (6)
C10	1.0528 (3)	0.57152 (19)	0.8392 (2)	0.0299 (6)
H10	1.126374	0.583905	0.895815	0.036*
C11	1.1130 (3)	0.5422 (2)	0.7444 (2)	0.0294 (6)
H11	1.226895	0.535041	0.736077	0.035*
C12	1.0071 (3)	0.52333 (18)	0.6620 (2)	0.0249 (6)
H12	1.047530	0.503204	0.596579	0.030*
C13	0.5980 (3)	0.5761 (2)	0.7852 (2)	0.0291 (6)
H13A	0.542286	0.578976	0.716866	0.044*
H13B	0.578180	0.634742	0.823689	0.044*
H13C	0.556474	0.522395	0.824971	0.044*
C14	0.8264 (4)	0.6143 (2)	0.9586 (2)	0.0349 (7)
H14A	0.918902	0.623555	1.007098	0.052*
H14B	0.754217	0.565655	0.986298	0.052*
H14C	0.766435	0.673737	0.950595	0.052*
N1	0.7344 (3)	0.51231 (14)	0.58726 (16)	0.0194 (5)
O1	0.8517 (2)	0.35517 (12)	0.54650 (13)	0.0237 (4)
O2	0.5832 (2)	0.40294 (13)	0.47232 (14)	0.0241 (4)
S1	0.69924 (7)	0.40208 (4)	0.55760 (4)	0.0177 (3)
CL1	0.75874 (9)	0.25743 (5)	0.94545 (5)	0.0355 (3)
CL2	0.16538 (7)	0.28217 (5)	0.76316 (6)	0.0356 (3)
H1	0.647 (3)	0.5457 (18)	0.585 (2)	0.017 (7)*

	U11	U22	U33	U12	U13	U23
C1	0.0190 (12)	0.0141 (11)	0.0178 (11)	−0.0010 (8)	0.0013 (9)	−0.0029 (9)
C2	0.0169 (12)	0.0171 (12)	0.0225 (12)	−0.0005 (9)	−0.0019 (9)	−0.0001 (9)
C3	0.0289 (14)	0.0171 (12)	0.0202 (13)	0.0006 (10)	−0.0053 (10)	0.0011 (9)
C4	0.0305 (15)	0.0193 (12)	0.0195 (13)	−0.0011 (10)	0.0068 (11)	0.0018 (10)
C5	0.0170 (12)	0.0185 (12)	0.0288 (13)	−0.0018 (9)	0.0041 (10)	−0.0033 (10)
C6	0.0191 (12)	0.0184 (12)	0.0196 (12)	0.0006 (9)	−0.0019 (10)	−0.0019 (9)
C7	0.0242 (13)	0.0164 (12)	0.0194 (12)	−0.0042 (9)	−0.0008 (10)	0.0030 (9)
C8	0.0254 (13)	0.0159 (12)	0.0229 (13)	0.0000 (10)	0.0012 (10)	0.0023 (9)
C9	0.0360 (15)	0.0178 (13)	0.0224 (14)	−0.0012 (10)	−0.0033 (11)	0.0012 (9)
C10	0.0322 (15)	0.0249 (14)	0.0322 (15)	−0.0020 (11)	−0.0100 (12)	0.0009 (11)
C11	0.0212 (13)	0.0273 (14)	0.0395 (16)	−0.0026 (10)	−0.0032 (12)	−0.0011 (12)
C12	0.0243 (13)	0.0208 (13)	0.0296 (14)	−0.0044 (10)	0.0044 (10)	−0.0020 (10)
C13	0.0300 (15)	0.0337 (15)	0.0235 (14)	0.0046 (11)	0.0012 (11)	−0.0033 (11)
C14	0.0444 (18)	0.0376 (17)	0.0225 (14)	0.0008 (13)	−0.0048 (13)	−0.0040 (12)
N1	0.0201 (11)	0.0197 (11)	0.0183 (10)	−0.0014 (8)	0.0001 (8)	0.0010 (8)
O1	0.0220 (9)	0.0251 (10)	0.0243 (9)	−0.0009 (7)	0.0067 (7)	−0.0038 (7)
O2	0.0294 (10)	0.0275 (10)	0.0153 (9)	−0.0031 (7)	−0.0014 (7)	−0.0009 (7)
S1	0.0193 (4)	0.0196 (4)	0.0144 (4)	−0.0022 (2)	0.0020 (3)	−0.0011 (2)
CL1	0.0443 (5)	0.0343 (5)	0.0270 (5)	−0.0034 (3)	−0.0159 (3)	0.0102 (3)
CL2	0.0172 (4)	0.0395 (5)	0.0504 (5)	−0.0054 (2)	0.0073 (3)	0.0049 (3)

C1—C2	1.385 (3)	C9—C10	1.382 (4)
C1—C6	1.392 (3)	C9—C14	1.512 (4)
C1—S1	1.776 (2)	C10—C11	1.384 (4)
C2—C3	1.379 (4)	C10—H10	0.9500
C2—H2	0.9500	C11—C12	1.380 (4)
C3—C4	1.379 (4)	C11—H11	0.9500
C3—CL1	1.741 (3)	C12—H12	0.9500
C4—C5	1.387 (4)	C13—H13A	0.9800
C4—H4	0.9500	C13—H13B	0.9800
C5—C6	1.383 (3)	C13—H13C	0.9800
C5—CL2	1.734 (2)	C14—H14A	0.9800
C6—H6	0.9500	C14—H14B	0.9800
C7—C12	1.390 (4)	C14—H14C	0.9800
C7—C8	1.398 (4)	N1—S1	1.630 (2)
C7—N1	1.446 (3)	N1—H1	0.862 (17)
C8—C9	1.410 (4)	O1—S1	1.4285 (18)
C8—C13	1.501 (4)	O2—S1	1.4346 (19)
C2—C1—C6	122.4 (2)	C11—C10—H10	119.3
C2—C1—S1	117.50 (17)	C12—C11—C10	119.8 (2)
C6—C1—S1	120.02 (18)	C12—C11—H11	120.1
C3—C2—C1	117.6 (2)	C10—C11—H11	120.1
C3—C2—H2	121.2	C11—C12—C7	119.4 (2)
C1—C2—H2	121.2	C11—C12—H12	120.3
C2—C3—C4	122.5 (2)	C7—C12—H12	120.3
C2—C3—CL1	118.3 (2)	C8—C13—H13A	109.5
C4—C3—CL1	119.19 (19)	C8—C13—H13B	109.5
C3—C4—C5	117.8 (2)	H13A—C13—H13B	109.5
C3—C4—H4	121.1	C8—C13—H13C	109.5
C5—C4—H4	121.1	H13A—C13—H13C	109.5
C6—C5—C4	122.4 (2)	H13B—C13—H13C	109.5
C6—C5—CL2	119.05 (19)	C9—C14—H14A	109.5
C4—C5—CL2	118.49 (19)	C9—C14—H14B	109.5
C5—C6—C1	117.1 (2)	H14A—C14—H14B	109.5
C5—C6—H6	121.4	C9—C14—H14C	109.5
C1—C6—H6	121.4	H14A—C14—H14C	109.5
C12—C7—C8	121.8 (2)	H14B—C14—H14C	109.5
C12—C7—N1	117.5 (2)	C7—N1—S1	119.12 (16)
C8—C7—N1	120.7 (2)	C7—N1—H1	113.9 (19)
C7—C8—C9	117.8 (2)	S1—N1—H1	111.8 (19)
C7—C8—C13	122.1 (2)	O1—S1—O2	119.99 (11)
C9—C8—C13	120.1 (2)	O1—S1—N1	108.44 (11)
C10—C9—C8	119.8 (2)	O2—S1—N1	106.30 (11)
C10—C9—C14	119.9 (3)	O1—S1—C1	106.41 (11)
C8—C9—C14	120.3 (2)	O2—S1—C1	108.61 (11)
C9—C10—C11	121.4 (3)	N1—S1—C1	106.38 (10)
C9—C10—H10	119.3
C6—C1—C2—C3	0.2 (3)	C13—C8—C9—C14	0.9 (4)
S1—C1—C2—C3	177.68 (17)	C8—C9—C10—C11	0.5 (4)
C1—C2—C3—C4	1.5 (4)	C14—C9—C10—C11	179.3 (3)
C1—C2—C3—CL1	−179.10 (18)	C9—C10—C11—C12	−0.5 (4)
C2—C3—C4—C5	−1.3 (4)	C10—C11—C12—C7	0.0 (4)
CL1—C3—C4—C5	179.28 (19)	C8—C7—C12—C11	0.5 (4)
C3—C4—C5—C6	−0.6 (4)	N1—C7—C12—C11	−179.2 (2)
C3—C4—C5—CL2	178.04 (19)	C12—C7—N1—S1	76.0 (3)
C4—C5—C6—C1	2.2 (4)	C8—C7—N1—S1	−103.7 (2)
CL2—C5—C6—C1	−176.42 (17)	C7—N1—S1—O1	−53.25 (19)
C2—C1—C6—C5	−2.0 (3)	C7—N1—S1—O2	176.48 (17)
S1—C1—C6—C5	−179.40 (17)	C7—N1—S1—C1	60.9 (2)
C12—C7—C8—C9	−0.4 (4)	C2—C1—S1—O1	36.2 (2)
N1—C7—C8—C9	179.3 (2)	C6—C1—S1—O1	−146.31 (18)
C12—C7—C8—C13	179.9 (2)	C2—C1—S1—O2	166.63 (17)
N1—C7—C8—C13	−0.4 (4)	C6—C1—S1—O2	−15.9 (2)
C7—C8—C9—C10	−0.1 (4)	C2—C1—S1—N1	−79.3 (2)
C13—C8—C9—C10	179.6 (2)	C6—C1—S1—N1	98.2 (2)
C7—C8—C9—C14	−178.8 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2i	0.86	2.14	2.9590	159
C4—H4···O1ii	0.95	2.41	3.332 (3)	164

C14H13Cl2NO2S	F(000) = 340
Mr = 330.21	Prism
Triclinic, P1	Dx = 1.468 Mg m−3
Hall symbol: -P 1	Melting point: 445 K
a = 8.4817 (15) Å	Cu Kα radiation, λ = 1.54178 Å
b = 8.6149 (15) Å	Cell parameters from 127 reflections
c = 12.167 (2) Å	θ = 7.7–63.7°
α = 109.875 (5)°	µ = 5.22 mm−1
β = 91.900 (5)°	T = 100 K
γ = 114.190 (5)°	Prism, colourless
V = 747.1 (2) Å3	0.29 × 0.26 × 0.22 mm
Z = 2

Bruker APEXII CCD area detector diffractometer	2400 independent reflections
Radiation source: fine-focus sealed tube	1960 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.124
phi and φ scans	θmax = 63.7°, θmin = 7.7°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −9→9
Tmin = 0.275, Tmax = 0.317	k = −9→9
6977 measured reflections	l = −14→14

Refinement on F2	1 restraint
Least-squares matrix: full	Hydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.074	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.233	w = 1/[σ2(Fo2) + (0.1757P)2 + 0.6254P] where P = (Fo2 + 2Fc2)/3
S = 1.02	(Δ/σ)max < 0.001
2400 reflections	Δρmax = 0.99 e Å−3
187 parameters	Δρmin = −0.60 e Å−3

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.

	x	y	z	Uiso*/Ueq
C1	0.8417 (4)	0.5358 (5)	0.1002 (4)	0.0203 (9)
C2	0.7459 (5)	0.3554 (5)	0.0217 (4)	0.0241 (10)
H2	0.644651	0.320522	−0.034335	0.029*
C3	0.8001 (5)	0.2253 (6)	0.0260 (4)	0.0249 (10)
C4	0.9467 (5)	0.2750 (6)	0.1103 (4)	0.0293 (11)
H4	0.981555	0.185462	0.115199	0.035*
C5	1.0386 (5)	0.4578 (6)	0.1860 (4)	0.0244 (9)
C6	0.9904 (5)	0.5912 (6)	0.1831 (4)	0.0238 (10)
H6	1.056523	0.716677	0.235918	0.029*
C7	0.6763 (5)	0.7502 (5)	0.3150 (4)	0.0211 (9)
C8	0.6651 (5)	0.6237 (6)	0.3668 (4)	0.0236 (9)
C9	0.7175 (5)	0.6907 (7)	0.4904 (5)	0.0317 (10)
H9	0.712684	0.607766	0.526909	0.038*
C10	0.7765 (7)	0.8761 (8)	0.5608 (5)	0.0444 (13)
H10	0.813297	0.919881	0.644715	0.053*
C11	0.7815 (7)	0.9971 (7)	0.5082 (5)	0.0438 (13)
H11	0.821341	1.123758	0.557153	0.053*
C12	0.7300 (6)	0.9386 (6)	0.3863 (4)	0.0316 (10)
C13	0.5959 (5)	0.4220 (6)	0.2945 (4)	0.0310 (11)
H13A	0.693639	0.395208	0.269174	0.046*
H13B	0.509594	0.386272	0.223963	0.046*
H13C	0.539097	0.352168	0.342708	0.046*
C14	0.7304 (8)	1.0734 (7)	0.3333 (6)	0.0472 (14)
H14A	0.728356	1.180297	0.395426	0.071*
H14B	0.626024	1.013250	0.269485	0.071*
H14C	0.837145	1.114337	0.300552	0.071*
N1	0.6231 (4)	0.6893 (4)	0.1889 (3)	0.0201 (8)
O1	0.9163 (3)	0.8797 (4)	0.1562 (3)	0.0251 (7)
O2	0.6731 (3)	0.6436 (4)	−0.0152 (3)	0.0230 (7)
S1	0.76785 (10)	0.70217 (12)	0.10237 (9)	0.0183 (4)
CL1	0.68515 (13)	−0.00070 (13)	−0.07437 (12)	0.0365 (4)
CL2	1.22462 (13)	0.52449 (17)	0.28944 (10)	0.0372 (4)
H1	0.529 (4)	0.590 (4)	0.154 (4)	0.029 (13)*

	U11	U22	U33	U12	U13	U23
C1	0.0210 (17)	0.0232 (19)	0.021 (2)	0.0095 (15)	0.0048 (14)	0.0138 (18)
C2	0.0242 (19)	0.028 (2)	0.026 (3)	0.0125 (17)	0.0086 (16)	0.015 (2)
C3	0.0255 (19)	0.025 (2)	0.030 (3)	0.0108 (16)	0.0127 (17)	0.017 (2)
C4	0.036 (2)	0.037 (2)	0.036 (3)	0.0227 (19)	0.018 (2)	0.028 (2)
C5	0.0274 (19)	0.036 (2)	0.020 (3)	0.0176 (17)	0.0061 (16)	0.017 (2)
C6	0.0248 (19)	0.031 (2)	0.021 (3)	0.0132 (17)	0.0061 (16)	0.0152 (19)
C7	0.0243 (18)	0.023 (2)	0.017 (2)	0.0111 (15)	0.0018 (14)	0.0093 (18)
C8	0.0214 (18)	0.027 (2)	0.027 (3)	0.0112 (16)	0.0060 (15)	0.0163 (19)
C9	0.036 (2)	0.039 (2)	0.028 (3)	0.0152 (19)	0.0064 (17)	0.024 (2)
C10	0.054 (3)	0.047 (3)	0.016 (3)	0.009 (2)	0.002 (2)	0.011 (2)
C11	0.071 (3)	0.025 (2)	0.019 (3)	0.012 (2)	0.004 (2)	0.003 (2)
C12	0.046 (2)	0.026 (2)	0.018 (3)	0.0152 (18)	0.0054 (17)	0.0052 (19)
C13	0.037 (2)	0.037 (2)	0.035 (3)	0.0208 (19)	0.0160 (18)	0.025 (2)
C14	0.084 (4)	0.028 (2)	0.038 (4)	0.032 (2)	0.014 (3)	0.014 (2)
N1	0.0240 (16)	0.0213 (17)	0.014 (2)	0.0091 (14)	0.0001 (13)	0.0080 (15)
O1	0.0289 (14)	0.0217 (14)	0.0246 (19)	0.0094 (12)	0.0039 (11)	0.0114 (13)
O2	0.0277 (13)	0.0266 (15)	0.0197 (19)	0.0136 (11)	0.0048 (11)	0.0128 (13)
S1	0.0223 (6)	0.0178 (6)	0.0160 (7)	0.0090 (4)	0.0011 (4)	0.0080 (5)
CL1	0.0340 (6)	0.0203 (6)	0.0533 (10)	0.0120 (5)	0.0106 (5)	0.0121 (6)
CL2	0.0392 (7)	0.0598 (8)	0.0266 (8)	0.0335 (6)	0.0034 (5)	0.0189 (6)

C1—C2	1.375 (6)	C9—C10	1.386 (8)
C1—C6	1.389 (6)	C9—H9	0.9500
C1—S1	1.777 (4)	C10—C11	1.385 (8)
C2—C3	1.390 (6)	C10—H10	0.9500
C2—H2	0.9500	C11—C12	1.383 (7)
C3—C4	1.401 (6)	C11—H11	0.9500
C3—CL1	1.726 (4)	C12—C14	1.506 (7)
C4—C5	1.377 (6)	C13—H13A	0.9800
C4—H4	0.9500	C13—H13B	0.9800
C5—C6	1.379 (6)	C13—H13C	0.9800
C5—CL2	1.743 (4)	C14—H14A	0.9800
C6—H6	0.9500	C14—H14B	0.9800
C7—C8	1.407 (6)	C14—H14C	0.9800
C7—C12	1.417 (6)	N1—S1	1.638 (3)
C7—N1	1.430 (5)	N1—H1	0.85 (2)
C8—C9	1.395 (6)	O1—S1	1.428 (3)
C8—C13	1.493 (6)	O2—S1	1.431 (3)
C2—C1—C6	122.0 (4)	C11—C10—H10	120.2
C2—C1—S1	119.5 (3)	C12—C11—C10	121.8 (5)
C6—C1—S1	118.3 (3)	C12—C11—H11	119.1
C1—C2—C3	118.7 (4)	C10—C11—H11	119.1
C1—C2—H2	120.7	C11—C12—C7	117.9 (5)
C3—C2—H2	120.7	C11—C12—C14	120.1 (4)
C2—C3—C4	120.9 (4)	C7—C12—C14	122.0 (4)
C2—C3—CL1	119.4 (3)	C8—C13—H13A	109.5
C4—C3—CL1	119.6 (3)	C8—C13—H13B	109.5
C5—C4—C3	117.8 (4)	H13A—C13—H13B	109.5
C5—C4—H4	121.1	C8—C13—H13C	109.5
C3—C4—H4	121.1	H13A—C13—H13C	109.5
C6—C5—C4	122.8 (4)	H13B—C13—H13C	109.5
C6—C5—CL2	118.4 (3)	C12—C14—H14A	109.5
C4—C5—CL2	118.8 (3)	C12—C14—H14B	109.5
C5—C6—C1	117.6 (4)	H14A—C14—H14B	109.5
C5—C6—H6	121.2	C12—C14—H14C	109.5
C1—C6—H6	121.2	H14A—C14—H14C	109.5
C8—C7—C12	121.2 (4)	H14B—C14—H14C	109.5
C8—C7—N1	120.7 (4)	C7—N1—S1	120.9 (2)
C12—C7—N1	118.0 (4)	C7—N1—H1	118 (4)
C9—C8—C7	118.2 (4)	S1—N1—H1	109 (3)
C9—C8—C13	119.6 (4)	O1—S1—O2	120.06 (18)
C7—C8—C13	122.2 (4)	O1—S1—N1	108.41 (17)
C10—C9—C8	121.2 (5)	O2—S1—N1	106.27 (16)
C10—C9—H9	119.4	O1—S1—C1	107.28 (17)
C8—C9—H9	119.4	O2—S1—C1	107.33 (18)
C9—C10—C11	119.6 (5)	N1—S1—C1	106.81 (17)
C9—C10—H10	120.2
C6—C1—C2—C3	0.1 (6)	C9—C10—C11—C12	−0.4 (8)
S1—C1—C2—C3	−176.4 (3)	C10—C11—C12—C7	−1.9 (8)
C1—C2—C3—C4	1.6 (6)	C10—C11—C12—C14	177.5 (5)
C1—C2—C3—CL1	−178.3 (3)	C8—C7—C12—C11	3.8 (6)
C2—C3—C4—C5	−2.2 (6)	N1—C7—C12—C11	180.0 (4)
CL1—C3—C4—C5	177.7 (3)	C8—C7—C12—C14	−175.5 (4)
C3—C4—C5—C6	1.1 (6)	N1—C7—C12—C14	0.7 (6)
C3—C4—C5—CL2	−178.5 (3)	C8—C7—N1—S1	−96.3 (4)
C4—C5—C6—C1	0.5 (6)	C12—C7—N1—S1	87.5 (4)
CL2—C5—C6—C1	−179.9 (3)	C7—N1—S1—O1	−45.5 (3)
C2—C1—C6—C5	−1.1 (6)	C7—N1—S1—O2	−175.8 (3)
S1—C1—C6—C5	175.4 (3)	C7—N1—S1—C1	69.8 (3)
C12—C7—C8—C9	−3.4 (5)	C2—C1—S1—O1	−159.3 (3)
N1—C7—C8—C9	−179.5 (3)	C6—C1—S1—O1	24.1 (4)
C12—C7—C8—C13	175.3 (4)	C2—C1—S1—O2	−29.0 (4)
N1—C7—C8—C13	−0.8 (5)	C6—C1—S1—O2	154.4 (3)
C7—C8—C9—C10	1.0 (6)	C2—C1—S1—N1	84.6 (4)
C13—C8—C9—C10	−177.7 (4)	C6—C1—S1—N1	−92.0 (3)
C8—C9—C10—C11	0.9 (7)

D—H···A	D—H	H···A	D···A	D—H···A
C14—H14C···O1	0.98	2.53	3.139 (8)	120
N1—H1···O2i	0.85 (4)	2.12 (4)	2.937 (5)	160 (4)
C13—H13A···Cg1	0.98	2.67	3.493 (5)	142

C14H13Cl2NO2S	Prism
Mr = 330.21	Dx = 1.496 Mg m−3
Monoclinic, P21/c	Melting point: 462 K
Hall symbol: -P 2ybc	Cu Kα radiation, λ = 1.54178 Å
a = 12.2268 (6) Å	Cell parameters from 128 reflections
b = 7.0399 (3) Å	θ = 6.8–64.4°
c = 17.3130 (8) Å	µ = 5.32 mm−1
β = 100.409 (1)°	T = 100 K
V = 1465.70 (12) Å3	Prism, colourless
Z = 4	0.27 × 0.24 × 0.21 mm
F(000) = 680

Bruker APEXII CCD area detector diffractometer	2412 independent reflections
Radiation source: fine-focus sealed tube	2374 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.056
phi and φ scans	θmax = 64.4°, θmin = 6.8°
Absorption correction: multi-scan (SADABS; Bruker,2009)	h = −14→14
Tmin = 0.297, Tmax = 0.327	k = −8→7
11468 measured reflections	l = −19→20

Refinement on F2	1 restraint
Least-squares matrix: full	Hydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.058	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.152	w = 1/[σ2(Fo2) + (0.1156P)2 + 2.094P] where P = (Fo2 + 2Fc2)/3
S = 0.99	(Δ/σ)max = 0.001
2412 reflections	Δρmax = 0.82 e Å−3
187 parameters	Δρmin = −0.88 e Å−3

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.

	x	y	z	Uiso*/Ueq
C1	0.4234 (2)	0.1933 (4)	0.62264 (15)	0.0107 (6)
C2	0.5280 (2)	0.2511 (4)	0.61112 (15)	0.0120 (6)
H2	0.586016	0.277777	0.654187	0.014*
C3	0.5443 (2)	0.2682 (4)	0.53442 (15)	0.0120 (6)
C4	0.4606 (2)	0.2341 (4)	0.47057 (15)	0.0138 (6)
H4	0.473647	0.246812	0.418356	0.017*
C5	0.3574 (2)	0.1810 (4)	0.48539 (16)	0.0133 (6)
C6	0.3366 (2)	0.1572 (4)	0.56068 (16)	0.0128 (6)
H6	0.265674	0.117738	0.569706	0.015*
C7	0.2216 (2)	0.4234 (4)	0.69407 (14)	0.0108 (6)
C8	0.2040 (2)	0.5888 (4)	0.64942 (15)	0.0126 (6)
H8	0.264930	0.668527	0.644084	0.015*
C9	0.0966 (2)	0.6368 (4)	0.61262 (16)	0.0146 (6)
C10	0.0089 (2)	0.5168 (4)	0.62049 (15)	0.0161 (6)
H10	−0.063981	0.547186	0.593959	0.019*
C11	0.0254 (2)	0.3533 (4)	0.66637 (16)	0.0144 (6)
C12	0.1329 (2)	0.3073 (4)	0.70360 (15)	0.0124 (6)
H12	0.145662	0.196778	0.735448	0.015*
C13	0.0756 (3)	0.8176 (4)	0.5651 (2)	0.0242 (7)
H13A	−0.000712	0.816863	0.535489	0.036*
H13B	0.127963	0.825736	0.528605	0.036*
H13C	0.085778	0.927260	0.600562	0.036*
C14	−0.0718 (2)	0.2318 (5)	0.67730 (18)	0.0244 (7)
H14A	−0.117650	0.300752	0.708934	0.037*
H14B	−0.044640	0.113872	0.704178	0.037*
H14C	−0.116566	0.201609	0.625895	0.037*
N1	0.33273 (18)	0.3807 (3)	0.73296 (12)	0.0111 (5)
O1	0.49846 (16)	0.1842 (3)	0.77286 (11)	0.0169 (5)
O2	0.31742 (16)	0.0286 (3)	0.72152 (11)	0.0159 (5)
S1	0.39385 (5)	0.18095 (9)	0.71907 (3)	0.0102 (3)
CL1	0.67420 (5)	0.33657 (9)	0.51672 (4)	0.0189 (3)
CL2	0.24931 (6)	0.14477 (11)	0.40666 (4)	0.0212 (3)
H1	0.379 (3)	0.475 (4)	0.739 (2)	0.027 (9)*

	U11	U22	U33	U12	U13	U23
C1	0.0138 (14)	0.0084 (12)	0.0104 (13)	0.0043 (10)	0.0040 (10)	0.0001 (9)
C2	0.0122 (13)	0.0108 (14)	0.0122 (13)	0.0013 (10)	0.0003 (10)	0.0004 (10)
C3	0.0135 (13)	0.0064 (13)	0.0175 (14)	0.0022 (10)	0.0066 (11)	0.0016 (10)
C4	0.0214 (14)	0.0108 (13)	0.0105 (13)	0.0039 (11)	0.0067 (11)	0.0022 (10)
C5	0.0161 (14)	0.0116 (14)	0.0111 (14)	0.0037 (10)	−0.0010 (11)	−0.0026 (10)
C6	0.0122 (13)	0.0117 (13)	0.0153 (14)	−0.0003 (9)	0.0043 (11)	0.0001 (10)
C7	0.0122 (13)	0.0148 (14)	0.0060 (11)	0.0012 (10)	0.0036 (10)	−0.0044 (10)
C8	0.0132 (13)	0.0133 (13)	0.0131 (13)	−0.0017 (10)	0.0071 (10)	−0.0018 (10)
C9	0.0170 (14)	0.0159 (14)	0.0116 (13)	0.0027 (11)	0.0044 (11)	0.0020 (10)
C10	0.0122 (13)	0.0231 (15)	0.0124 (13)	0.0024 (11)	0.0004 (10)	0.0007 (11)
C11	0.0137 (14)	0.0188 (14)	0.0109 (13)	−0.0026 (11)	0.0027 (11)	−0.0014 (10)
C12	0.0142 (13)	0.0157 (14)	0.0072 (12)	0.0007 (10)	0.0019 (10)	0.0006 (10)
C13	0.0195 (15)	0.0220 (16)	0.0321 (18)	0.0041 (12)	0.0072 (13)	0.0111 (13)
C14	0.0128 (13)	0.0310 (17)	0.0271 (16)	−0.0065 (13)	−0.0021 (12)	0.0065 (13)
N1	0.0103 (11)	0.0123 (12)	0.0108 (11)	−0.0017 (9)	0.0021 (9)	−0.0031 (9)
O1	0.0134 (10)	0.0264 (11)	0.0097 (10)	0.0052 (8)	−0.0014 (8)	0.0020 (8)
O2	0.0191 (10)	0.0123 (10)	0.0179 (10)	−0.0004 (8)	0.0072 (8)	0.0037 (7)
S1	0.0103 (4)	0.0134 (4)	0.0068 (4)	0.0015 (2)	0.0015 (3)	0.0016 (2)
CL1	0.0142 (4)	0.0199 (4)	0.0255 (5)	−0.0004 (2)	0.0112 (3)	0.0027 (2)
CL2	0.0202 (4)	0.0311 (5)	0.0103 (4)	−0.0013 (3)	−0.0029 (3)	−0.0028 (3)

C1—C6	1.389 (4)	C9—C10	1.391 (4)
C1—C2	1.391 (4)	C9—C13	1.512 (4)
C1—S1	1.773 (3)	C10—C11	1.393 (4)
C2—C3	1.383 (4)	C10—H10	0.9500
C2—H2	0.9500	C11—C12	1.394 (4)
C3—C4	1.385 (4)	C11—C14	1.504 (4)
C3—CL1	1.739 (3)	C12—H12	0.9500
C4—C5	1.385 (4)	C13—H13A	0.9800
C4—H4	0.9500	C13—H13B	0.9800
C5—C6	1.382 (4)	C13—H13C	0.9800
C5—CL2	1.737 (3)	C14—H14A	0.9800
C6—H6	0.9500	C14—H14B	0.9800
C7—C12	1.392 (4)	C14—H14C	0.9800
C7—C8	1.393 (4)	N1—S1	1.631 (2)
C7—N1	1.435 (3)	N1—H1	0.869 (19)
C8—C9	1.394 (4)	O1—S1	1.440 (2)
C8—H8	0.9500	O2—S1	1.428 (2)
C6—C1—C2	122.5 (2)	C11—C10—H10	119.2
C6—C1—S1	117.4 (2)	C10—C11—C12	118.9 (3)
C2—C1—S1	119.9 (2)	C10—C11—C14	120.3 (3)
C3—C2—C1	117.3 (2)	C12—C11—C14	120.7 (3)
C3—C2—H2	121.4	C7—C12—C11	119.9 (2)
C1—C2—H2	121.4	C7—C12—H12	120.0
C4—C3—C2	122.6 (2)	C11—C12—H12	120.0
C4—C3—CL1	118.27 (19)	C9—C13—H13A	109.5
C2—C3—CL1	119.2 (2)	C9—C13—H13B	109.5
C3—C4—C5	117.7 (2)	H13A—C13—H13B	109.5
C3—C4—H4	121.1	C9—C13—H13C	109.5
C5—C4—H4	121.1	H13A—C13—H13C	109.5
C6—C5—C4	122.4 (3)	H13B—C13—H13C	109.5
C6—C5—CL2	118.6 (2)	C11—C14—H14A	109.5
C4—C5—CL2	118.9 (2)	C11—C14—H14B	109.5
C5—C6—C1	117.5 (3)	H14A—C14—H14B	109.5
C5—C6—H6	121.3	C11—C14—H14C	109.5
C1—C6—H6	121.3	H14A—C14—H14C	109.5
C12—C7—C8	120.8 (2)	H14B—C14—H14C	109.5
C12—C7—N1	120.9 (2)	C7—N1—S1	122.12 (18)
C8—C7—N1	118.3 (2)	C7—N1—H1	116 (2)
C7—C8—C9	119.7 (2)	S1—N1—H1	112 (2)
C7—C8—H8	120.2	O2—S1—O1	120.14 (12)
C9—C8—H8	120.2	O2—S1—N1	108.89 (11)
C10—C9—C8	119.2 (2)	O1—S1—N1	105.56 (11)
C10—C9—C13	120.4 (3)	O2—S1—C1	108.09 (12)
C8—C9—C13	120.4 (3)	O1—S1—C1	107.45 (12)
C9—C10—C11	121.5 (2)	N1—S1—C1	105.85 (11)
C9—C10—H10	119.2
C6—C1—C2—C3	−1.3 (4)	C9—C10—C11—C12	−1.5 (4)
S1—C1—C2—C3	−176.48 (19)	C9—C10—C11—C14	176.7 (3)
C1—C2—C3—C4	1.4 (4)	C8—C7—C12—C11	1.9 (4)
C1—C2—C3—CL1	−179.05 (19)	N1—C7—C12—C11	178.9 (2)
C2—C3—C4—C5	0.0 (4)	C10—C11—C12—C7	−0.5 (4)
CL1—C3—C4—C5	−179.60 (19)	C14—C11—C12—C7	−178.7 (2)
C3—C4—C5—C6	−1.5 (4)	C12—C7—N1—S1	59.0 (3)
C3—C4—C5—CL2	177.90 (19)	C8—C7—N1—S1	−123.9 (2)
C4—C5—C6—C1	1.5 (4)	C7—N1—S1—O2	−44.7 (2)
CL2—C5—C6—C1	−177.86 (19)	C7—N1—S1—O1	−174.93 (19)
C2—C1—C6—C5	−0.1 (4)	C7—N1—S1—C1	71.3 (2)
S1—C1—C6—C5	175.20 (19)	C6—C1—S1—O2	37.4 (2)
C12—C7—C8—C9	−1.2 (4)	C2—C1—S1—O2	−147.2 (2)
N1—C7—C8—C9	−178.3 (2)	C6—C1—S1—O1	168.42 (19)
C7—C8—C9—C10	−0.7 (4)	C2—C1—S1—O1	−16.2 (2)
C7—C8—C9—C13	178.9 (2)	C6—C1—S1—N1	−79.1 (2)
C8—C9—C10—C11	2.1 (4)	C2—C1—S1—N1	96.2 (2)
C13—C9—C10—C11	−177.5 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1i	0.87	2.13	2.9848	167
C14—H14B···Cg2ii	0.98	2.86	3.5135	124