Chloro­thia­zide dimethyl sulfoxide solvate

Johnston, A.; Florence, A.J.; Fernandes, P.; Kennedy, A.R.

doi:10.1107/S1600536807016406

Chlorothiazide dimethyl sulfoxide solvate

A. Johnston, A. J. Florence, P. Fernandes and A. R. Kennedy

Chlorothiazide forms a 1:1 solvate with dimethyl sulfoxide (systematic name: 6-chloro-4H-1,2,4-benzothiadiazine-7-sulfonamide 1,1-dioxide dimethyl sulfoxide solvate), C₇H₆ClN₃O₄S₂·C₂H₆OS. The compound crystallizes with two molecules of solvent and two molecules of chlorothiazide in the asymmetric unit and displays an extensive network of hydrogen bonds.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807016406/at2266sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807016406/at2266Isup2.hkl Contains datablock I

CCDC reference: 647568

checkCIF report

Key indicators

Single-crystal X-ray study
T = 123 K
Mean (C-C) = 0.004 Å
R factor = 0.043
wR factor = 0.112
Data-to-parameter ratio = 15.7

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT154_ALERT_1_C The su's on the Cell Angles are Equal (x 10000)         200 Deg.
PLAT245_ALERT_2_C U(iso) H6N     Smaller than U(eq) N1A     by ...       0.01 AngSq
PLAT431_ALERT_2_C Short Inter HL..A Contact  Cl1    ..  O2      ..       3.20 Ang.
PLAT431_ALERT_2_C Short Inter HL..A Contact  Cl1A   ..  O4A     ..       3.12 Ang.

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   4 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   3 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Comment top

The title compound, (I), was synthesized by the same method as the similar compound chlorothiazide N,N-dimethylacetamide solvate (1/2) (Johnston, Florence, Fernandes et al., 2007). Here, we report the crystal structure of (I) determined by single-crystal X-ray diffraction (Fig. 1).

The molecules of (I) crystallize in space group P1 with two chlorothiazide (CT) and two dimethyl sulfoxide (DMSO) molecules in the asymmetric unit. Bond lengths and angles in the chlorothiazide group of (I) are

comparable with those of the related compound chlorothiazide N,N-dimethylacetamide solvate (1/2) (Johnston, Florence, Fernandes et al., 2007).

Hydrogen-bonded chains of CT molecules are formed via contacts 2 and 5 (Table 1) and connected to adjacent DMSO molecules via contacts 1, 3, 4 and 6 to form a layered structure of alternating CT and DMSO molecules (Fig. 2).

Related literature top

For related literature, see: Dupont & Dideberg (1970); Florence et al. (2003, 2006); Johnston, Florence, Fernandes et al. (2007); Johnston, Florence, Shankland et al. (2007); Shankland et al. (1997).

Experimental top

A single-crystal sample of the title compound, (I), was recrystallized from a saturated solution in dimethyl sulfoxide by isothermal solvent evaporation at 278 K.

Structure description top

comparable with those of the related compound chlorothiazide N,N-dimethylacetamide solvate (1/2) (Johnston, Florence, Fernandes et al., 2007).

Computing details top

Data collection: COLLECT (Nonius, 1998) and DENZO (Otwinowski & Minor, 1997); cell refinement: DENZO and COLLECT; data reduction: DENZO; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003) and ORTEP-3 (Farrugia, 1997; software used to prepare material for publication: SHELXL97.

Figures top

	Fig. 1. The asymmetric unit of (I), showing 50% probablility displacement ellipsoids.
	Fig. 2. A packing diagram for (I), showing alternating layers of CT and DMSO molecules, viewed down the b axis. Molecules are coloured by symmetry equivalence.

6-chloro-4H-1,2,4-benzothiadiazine-7-sulfonamide 1,1-dioxide dimethyl sulfoxide solvate top

Crystal data top

C₇H₆ClN₃O₄S₂·C₂H₆OS	Z = 4
M_r = 373.85	F(000) = 768
Triclinic, P1	D_x = 1.701 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.0965 (3) Å	Cell parameters from 6375 reflections
b = 11.2081 (4) Å	θ = 2.9–27.1°
c = 15.8916 (5) Å	µ = 0.71 mm⁻¹
α = 109.009 (2)°	T = 123 K
β = 103.384 (2)°	Cut block, colourless
γ = 96.246 (2)°	0.25 × 0.25 × 0.15 mm
V = 1460.07 (9) Å³

Data collection top

Nonius KappaCCD area-detector diffractometer	4748 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.057
Graphite monochromator	θ_max = 27.1°, θ_min = 3.1°
φ and ω scans	h = −11→11
36041 measured reflections	k = −14→14
6400 independent reflections	l = −20→20

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.112	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ²(F_o²) + (0.0496P)² + 1.3342P] where P = (F_o² + 2F_c²)/3
6400 reflections	(Δ/σ)_max = 0.001
407 parameters	Δρ_max = 0.71 e Å⁻³
0 restraints	Δρ_min = −0.52 e Å⁻³

Crystal data top

C₇H₆ClN₃O₄S₂·C₂H₆OS	γ = 96.246 (2)°
M_r = 373.85	V = 1460.07 (9) Å³
Triclinic, P1	Z = 4
a = 9.0965 (3) Å	Mo Kα radiation
b = 11.2081 (4) Å	µ = 0.71 mm⁻¹
c = 15.8916 (5) Å	T = 123 K
α = 109.009 (2)°	0.25 × 0.25 × 0.15 mm
β = 103.384 (2)°

Data collection top

Nonius KappaCCD area-detector diffractometer	4748 reflections with I > 2σ(I)
36041 measured reflections	R_int = 0.057
6400 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.043	0 restraints
wR(F²) = 0.112	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	Δρ_max = 0.71 e Å⁻³
6400 reflections	Δρ_min = −0.52 e Å⁻³
407 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
Cl1	0.78822 (8)	0.54314 (6)	0.48340 (5)	0.02664 (17)
Cl1A	0.22271 (8)	−0.04500 (6)	0.02658 (5)	0.02603 (17)
S1	0.19851 (7)	0.10617 (6)	0.29501 (5)	0.02128 (16)
S1A	0.78675 (8)	0.41554 (6)	0.19570 (5)	0.02323 (17)
S2	0.76779 (8)	0.28008 (6)	0.53626 (5)	0.02136 (16)
S2A	0.22252 (8)	0.19926 (6)	−0.04620 (5)	0.02154 (16)
O1	0.1121 (2)	0.12083 (19)	0.36173 (13)	0.0280 (5)
O1A	0.8685 (2)	0.4035 (2)	0.12706 (14)	0.0349 (5)
O3	0.2377 (2)	−0.01677 (18)	0.25809 (14)	0.0315 (5)
O3A	0.7356 (2)	0.53353 (18)	0.22984 (15)	0.0365 (5)
O2	0.8963 (2)	0.27955 (18)	0.49818 (13)	0.0257 (4)
O2A	0.2797 (2)	0.30466 (18)	−0.06949 (13)	0.0270 (4)
O4	0.7018 (2)	0.16690 (18)	0.54795 (13)	0.0270 (4)
O4A	0.0953 (2)	0.2041 (2)	−0.00693 (13)	0.0289 (5)
N3	0.0993 (3)	0.1405 (2)	0.20961 (16)	0.0241 (5)
N3A	0.8968 (3)	0.3918 (2)	0.28270 (15)	0.0242 (5)
N2	0.2675 (3)	0.3372 (2)	0.24384 (16)	0.0209 (5)
N2A	0.7405 (3)	0.1942 (2)	0.26051 (16)	0.0211 (5)
N1	0.8120 (3)	0.3972 (3)	0.63228 (18)	0.0299 (6)
N1A	0.1847 (3)	0.0712 (3)	−0.13469 (18)	0.0278 (6)
C3	0.1405 (3)	0.2460 (3)	0.19625 (18)	0.0227 (6)
H3	0.0724	0.2600	0.1468	0.027*
C3A	0.8641 (3)	0.2898 (3)	0.30293 (18)	0.0229 (6)
H3A	0.9369	0.2828	0.3538	0.027*
C2	0.3815 (3)	0.3307 (2)	0.31655 (18)	0.0190 (5)
C2A	0.6220 (3)	0.1890 (2)	0.18582 (18)	0.0182 (5)
C7	0.3671 (3)	0.2252 (2)	0.34459 (18)	0.0190 (5)
C7A	0.6268 (3)	0.2885 (2)	0.15053 (18)	0.0190 (5)
C1	0.4842 (3)	0.2148 (2)	0.41370 (18)	0.0199 (6)
H1	0.4739	0.1415	0.4311	0.024*
C1A	0.5055 (3)	0.2868 (2)	0.07812 (18)	0.0206 (6)
H1A	0.5092	0.3555	0.0556	0.025*
C5	0.6158 (3)	0.3102 (2)	0.45738 (18)	0.0199 (6)
C5A	0.3796 (3)	0.1857 (2)	0.03880 (18)	0.0193 (5)
C6	0.6271 (3)	0.4191 (2)	0.43066 (19)	0.0209 (6)
C6A	0.3772 (3)	0.0845 (2)	0.07322 (18)	0.0193 (5)
C4	0.5130 (3)	0.4285 (2)	0.36100 (18)	0.0202 (6)
H4	0.5234	0.5013	0.3431	0.024*
C4A	0.4955 (3)	0.0863 (2)	0.14576 (18)	0.0211 (6)
H4A	0.4911	0.0178	0.1685	0.025*
S3A	0.81126 (9)	0.94876 (7)	0.38266 (5)	0.02774 (18)
S3	0.27965 (11)	0.58546 (7)	0.12608 (5)	0.0363 (2)
O5A	0.7186 (2)	0.97587 (18)	0.29982 (13)	0.0262 (4)
O5	0.3151 (2)	0.56294 (19)	0.21714 (14)	0.0292 (5)
C8A	0.9157 (3)	0.8318 (3)	0.3362 (2)	0.0341 (7)
H8A	0.8484	0.7661	0.2784	0.051*
H9A	0.9523	0.7911	0.3810	0.051*
H10A	1.0041	0.8733	0.3234	0.051*
C9A	0.6747 (4)	0.8466 (3)	0.4064 (3)	0.0450 (9)
H11A	0.5953	0.8932	0.4249	0.068*
H12A	0.7274	0.8207	0.4569	0.068*
H13A	0.6264	0.7698	0.3506	0.068*
C8	0.4120 (4)	0.7282 (4)	0.1481 (3)	0.0505 (10)
H8	0.4029	0.7971	0.2024	0.076*
H9	0.3889	0.7540	0.0940	0.076*
H10	0.5173	0.7122	0.1602	0.076*
C9	0.1108 (4)	0.6518 (4)	0.1194 (3)	0.0667 (13)
H11	0.0234	0.5871	0.1133	0.100*
H12	0.0894	0.6777	0.0652	0.100*
H13	0.1263	0.7271	0.1758	0.100*
H1N	0.286 (4)	0.398 (3)	0.230 (2)	0.033 (9)*
H2N	0.893 (4)	0.450 (3)	0.647 (2)	0.033 (9)*
H3N	0.771 (4)	0.393 (3)	0.671 (2)	0.034 (10)*
H4N	0.737 (3)	0.137 (3)	0.2779 (19)	0.015 (7)*
H5N	0.110 (4)	0.023 (3)	−0.142 (2)	0.034 (10)*
H6N	0.218 (3)	0.070 (3)	−0.180 (2)	0.016 (7)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0221 (4)	0.0211 (3)	0.0306 (4)	−0.0037 (3)	0.0022 (3)	0.0076 (3)
Cl1A	0.0214 (3)	0.0224 (3)	0.0289 (4)	−0.0054 (3)	0.0015 (3)	0.0092 (3)
S1	0.0168 (3)	0.0201 (3)	0.0228 (4)	−0.0013 (3)	0.0014 (3)	0.0070 (3)
S1A	0.0189 (3)	0.0203 (3)	0.0263 (4)	−0.0031 (3)	0.0010 (3)	0.0091 (3)
S2	0.0173 (3)	0.0231 (3)	0.0218 (3)	0.0016 (3)	0.0023 (3)	0.0088 (3)
S2A	0.0176 (3)	0.0250 (4)	0.0207 (3)	0.0028 (3)	0.0023 (3)	0.0091 (3)
O1	0.0211 (10)	0.0343 (11)	0.0279 (11)	−0.0017 (8)	0.0057 (8)	0.0136 (9)
O1A	0.0268 (11)	0.0451 (13)	0.0325 (12)	−0.0064 (10)	0.0055 (9)	0.0200 (10)
O3	0.0284 (11)	0.0214 (10)	0.0351 (12)	−0.0002 (8)	0.0002 (9)	0.0059 (9)
O3A	0.0334 (12)	0.0166 (10)	0.0472 (13)	−0.0003 (9)	−0.0024 (10)	0.0071 (9)
O2	0.0196 (10)	0.0315 (11)	0.0273 (11)	0.0065 (8)	0.0064 (8)	0.0122 (9)
O2A	0.0268 (11)	0.0277 (11)	0.0263 (11)	0.0024 (8)	0.0019 (8)	0.0143 (9)
O4	0.0218 (10)	0.0277 (11)	0.0308 (11)	0.0024 (8)	0.0007 (8)	0.0153 (9)
O4A	0.0236 (11)	0.0397 (12)	0.0264 (11)	0.0099 (9)	0.0073 (9)	0.0146 (9)
N3	0.0201 (12)	0.0270 (12)	0.0209 (12)	−0.0008 (10)	0.0007 (9)	0.0084 (10)
N3A	0.0196 (12)	0.0273 (13)	0.0215 (12)	0.0003 (10)	0.0006 (9)	0.0084 (10)
N2	0.0216 (12)	0.0206 (12)	0.0214 (12)	0.0030 (10)	0.0045 (10)	0.0104 (10)
N2A	0.0224 (12)	0.0209 (12)	0.0215 (12)	0.0042 (10)	0.0043 (10)	0.0111 (10)
N1	0.0252 (14)	0.0360 (15)	0.0227 (14)	−0.0042 (12)	0.0053 (12)	0.0078 (12)
N1A	0.0253 (14)	0.0313 (14)	0.0202 (13)	−0.0058 (11)	0.0050 (11)	0.0055 (11)
C3	0.0208 (14)	0.0291 (15)	0.0196 (14)	0.0077 (12)	0.0052 (11)	0.0102 (12)
C3A	0.0186 (14)	0.0289 (15)	0.0188 (14)	0.0052 (11)	0.0028 (11)	0.0072 (11)
C2	0.0184 (13)	0.0211 (13)	0.0195 (13)	0.0060 (11)	0.0073 (11)	0.0079 (11)
C2A	0.0164 (13)	0.0195 (13)	0.0195 (13)	0.0039 (10)	0.0066 (10)	0.0068 (10)
C7	0.0181 (13)	0.0186 (13)	0.0199 (13)	0.0034 (10)	0.0060 (11)	0.0060 (11)
C7A	0.0169 (13)	0.0172 (13)	0.0197 (13)	−0.0001 (10)	0.0034 (11)	0.0050 (10)
C1	0.0181 (13)	0.0204 (13)	0.0221 (14)	0.0027 (11)	0.0064 (11)	0.0088 (11)
C1A	0.0236 (14)	0.0183 (13)	0.0212 (14)	0.0039 (11)	0.0066 (11)	0.0088 (11)
C5	0.0180 (13)	0.0223 (14)	0.0184 (13)	0.0033 (11)	0.0044 (11)	0.0067 (11)
C5A	0.0183 (13)	0.0201 (13)	0.0187 (13)	0.0039 (10)	0.0043 (11)	0.0066 (11)
C6	0.0160 (13)	0.0176 (13)	0.0247 (14)	−0.0016 (10)	0.0049 (11)	0.0043 (11)
C6A	0.0165 (13)	0.0160 (12)	0.0216 (14)	−0.0007 (10)	0.0042 (11)	0.0040 (10)
C4	0.0205 (14)	0.0176 (13)	0.0245 (14)	0.0032 (10)	0.0084 (11)	0.0090 (11)
C4A	0.0221 (14)	0.0189 (13)	0.0235 (14)	0.0034 (11)	0.0069 (11)	0.0090 (11)
S3A	0.0363 (4)	0.0231 (4)	0.0237 (4)	0.0067 (3)	0.0045 (3)	0.0110 (3)
S3	0.0579 (6)	0.0253 (4)	0.0265 (4)	0.0114 (4)	0.0091 (4)	0.0116 (3)
O5A	0.0290 (11)	0.0280 (11)	0.0263 (11)	0.0083 (9)	0.0067 (9)	0.0161 (9)
O5	0.0310 (11)	0.0316 (11)	0.0303 (11)	0.0071 (9)	0.0087 (9)	0.0178 (9)
C8A	0.0271 (16)	0.0289 (16)	0.0469 (19)	0.0074 (13)	0.0046 (14)	0.0178 (14)
C9A	0.053 (2)	0.052 (2)	0.050 (2)	0.0162 (18)	0.0238 (18)	0.0367 (18)
C8	0.041 (2)	0.063 (2)	0.073 (3)	0.0148 (18)	0.0268 (19)	0.048 (2)
C9	0.029 (2)	0.072 (3)	0.114 (4)	0.0059 (19)	0.003 (2)	0.067 (3)

Geometric parameters (Å, º) top

Cl1—C6	1.736 (3)	N1A—H5N	0.78 (4)
Cl1A—C6A	1.733 (3)	N1A—H6N	0.84 (3)
S1—O1	1.439 (2)	N2A—H4N	0.78 (3)
S1—N3	1.629 (3)	C1—C7	1.387 (4)
S1—C7	1.750 (3)	C1—C5	1.383 (4)
S1—O3	1.431 (2)	C2—C4	1.397 (4)
S2—O2	1.435 (2)	C2—C7	1.397 (3)
S2—N1	1.584 (3)	C4—C6	1.372 (4)
S2—C5	1.781 (3)	C5—C6	1.418 (4)
S2—O4	1.430 (2)	C1—H1	0.9500
S1A—O1A	1.436 (2)	C3—H3	0.9500
S1A—O3A	1.429 (2)	C4—H4	0.9500
S1A—N3A	1.625 (2)	C1A—C7A	1.391 (4)
S1A—C7A	1.749 (3)	C1A—C5A	1.382 (4)
S2A—O2A	1.430 (2)	C2A—C7A	1.403 (3)
S2A—O4A	1.434 (2)	C2A—C4A	1.396 (4)
S2A—N1A	1.584 (3)	C4A—C6A	1.376 (4)
S2A—C5A	1.782 (3)	C5A—C6A	1.411 (3)
S3A—C8A	1.770 (3)	C1A—H1A	0.9500
S3A—C9A	1.785 (4)	C3A—H3A	0.9500
S3A—O5A	1.529 (2)	C4A—H4A	0.9500
S3—O5	1.517 (2)	C8A—H10A	0.9800
S3—C8	1.776 (5)	C8A—H8A	0.9800
S3—C9	1.774 (4)	C8A—H9A	0.9800
N2—C3	1.337 (4)	C9A—H11A	0.9800
N2—C2	1.390 (4)	C9A—H12A	0.9800
N3—C3	1.299 (4)	C9A—H13A	0.9800
N1—H3N	0.80 (3)	C8—H8	0.9800
N1—H2N	0.83 (4)	C8—H9	0.9800
N2—H1N	0.79 (4)	C8—H10	0.9800
N2A—C3A	1.335 (4)	C9—H11	0.9800
N2A—C2A	1.387 (4)	C9—H12	0.9800
N3A—C3A	1.307 (4)	C9—H13	0.9800

O1—S1—O3	117.17 (13)	Cl1—C6—C5	120.9 (2)
O1—S1—N3	107.46 (13)	S1—C7—C1	119.00 (19)
O1—S1—C7	108.53 (13)	S1—C7—C2	120.4 (2)
O3—S1—N3	108.83 (13)	C1—C7—C2	120.6 (2)
O3—S1—C7	109.21 (12)	C7—C1—H1	120.00
N3—S1—C7	104.96 (13)	C5—C1—H1	120.00
O2—S2—O4	120.13 (13)	N3—C3—H3	116.00
O2—S2—N1	108.54 (14)	N2—C3—H3	116.00
O2—S2—C5	105.75 (12)	C2—C4—H4	120.00
O4—S2—N1	108.97 (15)	C6—C4—H4	120.00
O4—S2—C5	104.86 (12)	C5A—C1A—C7A	120.4 (2)
N1—S2—C5	107.96 (14)	N2A—C2A—C4A	120.7 (2)
O3A—S1A—N3A	108.85 (13)	N2A—C2A—C7A	120.2 (2)
O3A—S1A—C7A	108.47 (13)	C4A—C2A—C7A	119.1 (2)
N3A—S1A—C7A	105.22 (13)	N2A—C3A—N3A	127.7 (3)
O1A—S1A—O3A	117.48 (14)	C2A—C4A—C6A	119.8 (2)
O1A—S1A—N3A	107.72 (13)	S2A—C5A—C6A	124.1 (2)
O1A—S1A—C7A	108.43 (13)	C1A—C5A—C6A	118.7 (2)
O2A—S2A—O4A	120.19 (13)	S2A—C5A—C1A	117.00 (19)
O2A—S2A—N1A	108.56 (15)	Cl1A—C6A—C4A	117.83 (19)
O2A—S2A—C5A	105.70 (12)	Cl1A—C6A—C5A	120.8 (2)
N1A—S2A—C5A	106.90 (14)	C4A—C6A—C5A	121.3 (2)
O4A—S2A—N1A	109.18 (14)	S1A—C7A—C1A	118.89 (19)
O4A—S2A—C5A	105.52 (12)	C1A—C7A—C2A	120.6 (2)
C8A—S3A—C9A	97.75 (17)	S1A—C7A—C2A	120.5 (2)
O5A—S3A—C9A	104.75 (16)	C7A—C1A—H1A	120.00
O5A—S3A—C8A	105.48 (13)	C5A—C1A—H1A	120.00
O5—S3—C8	104.78 (17)	N3A—C3A—H3A	116.00
C8—S3—C9	97.3 (2)	N2A—C3A—H3A	116.00
O5—S3—C9	106.00 (17)	C2A—C4A—H4A	120.00
C2—N2—C3	123.8 (2)	C6A—C4A—H4A	120.00
S1—N3—C3	122.2 (2)	S3A—C8A—H9A	109.00
H2N—N1—H3N	120 (3)	H8A—C8A—H10A	109.00
S2—N1—H2N	118 (2)	S3A—C8A—H10A	109.00
S2—N1—H3N	119 (2)	H8A—C8A—H9A	109.00
C2—N2—H1N	115 (2)	S3A—C8A—H8A	109.00
C3—N2—H1N	122 (2)	H9A—C8A—H10A	110.00
C2A—N2A—C3A	124.1 (2)	S3A—C9A—H13A	110.00
S1A—N3A—C3A	122.1 (2)	H11A—C9A—H13A	109.00
S2A—N1A—H6N	120 (2)	H12A—C9A—H13A	109.00
S2A—N1A—H5N	115 (2)	H11A—C9A—H12A	109.00
H5N—N1A—H6N	120 (3)	S3A—C9A—H11A	109.00
C3A—N2A—H4N	117 (2)	S3A—C9A—H12A	109.00
C2A—N2A—H4N	119 (2)	S3—C8—H8	109.00
C5—C1—C7	120.5 (2)	S3—C8—H9	109.00
N2—C2—C4	120.2 (2)	S3—C8—H10	109.00
N2—C2—C7	120.4 (2)	H8—C8—H9	110.00
C4—C2—C7	119.4 (2)	H8—C8—H10	109.00
N2—C3—N3	127.7 (3)	H9—C8—H10	110.00
C2—C4—C6	119.8 (2)	S3—C9—H11	109.00
S2—C5—C1	117.00 (19)	S3—C9—H12	109.00
S2—C5—C6	124.2 (2)	S3—C9—H13	109.00
C1—C5—C6	118.5 (2)	H11—C9—H12	109.00
C4—C6—C5	121.2 (2)	H11—C9—H13	110.00
Cl1—C6—C4	117.87 (19)	H12—C9—H13	110.00

O1—S1—N3—C3	107.7 (3)	C3A—N2A—C2A—C7A	−0.4 (4)
O3—S1—N3—C3	−124.5 (2)	C2A—N2A—C3A—N3A	−0.7 (5)
C7—S1—N3—C3	−7.7 (3)	S1A—N3A—C3A—N2A	−1.9 (4)
O1—S1—C7—C1	72.2 (2)	C5—C1—C7—C2	1.4 (4)
O1—S1—C7—C2	−106.2 (2)	C5—C1—C7—S1	−176.9 (2)
O3—S1—C7—C1	−56.6 (3)	C7—C1—C5—S2	−173.6 (2)
O3—S1—C7—C2	125.0 (2)	C7—C1—C5—C6	0.8 (4)
N3—S1—C7—C1	−173.2 (2)	C7—C2—C4—C6	0.8 (4)
N3—S1—C7—C2	8.5 (3)	N2—C2—C7—S1	−5.2 (4)
O2—S2—C5—C1	117.5 (2)	N2—C2—C7—C1	176.5 (3)
O2—S2—C5—C6	−56.5 (3)	C4—C2—C7—S1	176.1 (2)
O4—S2—C5—C1	−10.4 (2)	N2—C2—C4—C6	−177.9 (3)
O4—S2—C5—C6	175.6 (2)	C4—C2—C7—C1	−2.2 (4)
N1—S2—C5—C1	−126.5 (2)	C2—C4—C6—Cl1	179.9 (2)
N1—S2—C5—C6	59.6 (3)	C2—C4—C6—C5	1.3 (4)
C7A—S1A—N3A—C3A	4.3 (3)	S2—C5—C6—C4	171.7 (2)
O1A—S1A—C7A—C1A	−69.2 (2)	C1—C5—C6—Cl1	179.4 (2)
O1A—S1A—C7A—C2A	109.9 (2)	C1—C5—C6—C4	−2.2 (4)
O3A—S1A—C7A—C1A	59.4 (3)	S2—C5—C6—Cl1	−6.8 (3)
O3A—S1A—C7A—C2A	−121.5 (2)	C7A—C1A—C5A—S2A	174.5 (2)
O1A—S1A—N3A—C3A	−111.2 (3)	C7A—C1A—C5A—C6A	−0.3 (4)
O3A—S1A—N3A—C3A	120.4 (2)	C5A—C1A—C7A—S1A	177.9 (2)
N3A—S1A—C7A—C2A	−5.2 (3)	C5A—C1A—C7A—C2A	−1.2 (4)
N3A—S1A—C7A—C1A	175.8 (2)	N2A—C2A—C4A—C6A	178.4 (3)
O4A—S2A—C5A—C6A	58.8 (3)	C7A—C2A—C4A—C6A	−0.6 (4)
O4A—S2A—C5A—C1A	−115.6 (2)	N2A—C2A—C7A—S1A	3.6 (4)
O2A—S2A—C5A—C1A	12.7 (2)	N2A—C2A—C7A—C1A	−177.3 (3)
N1A—S2A—C5A—C1A	128.2 (2)	C4A—C2A—C7A—S1A	−177.4 (2)
N1A—S2A—C5A—C6A	−57.3 (3)	C4A—C2A—C7A—C1A	1.6 (4)
O2A—S2A—C5A—C6A	−172.8 (2)	C2A—C4A—C6A—Cl1A	−179.7 (2)
C2—N2—C3—N3	1.8 (5)	C2A—C4A—C6A—C5A	−0.9 (4)
C3—N2—C2—C4	178.1 (3)	S2A—C5A—C6A—Cl1A	5.8 (3)
C3—N2—C2—C7	−0.6 (4)	S2A—C5A—C6A—C4A	−173.0 (2)
S1—N3—C3—N2	3.5 (4)	C1A—C5A—C6A—Cl1A	−179.9 (2)
C3A—N2A—C2A—C4A	−179.3 (3)	C1A—C5A—C6A—C4A	1.3 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H1N···O5	0.80 (3)	1.92 (3)	2.704 (3)	168 (3)
N1—H2N···N3Aⁱ	0.83 (3)	2.24 (4)	3.055 (4)	167 (3)
N1—H3N···O5ⁱⁱ	0.80 (3)	2.04 (3)	2.821 (3)	164 (3)
N2A—H4N···O5Aⁱⁱⁱ	0.78 (3)	1.94 (3)	2.714 (3)	171 (3)
N1A—H5N···N3^iv	0.78 (3)	2.27 (4)	3.020 (3)	162 (3)
N1A—H6N···O5A^v	0.85 (3)	2.03 (3)	2.865 (3)	167 (3)

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

Experimental details

Crystal data
Chemical formula	C₇H₆ClN₃O₄S₂·C₂H₆OS
M_r	373.85
Crystal system, space group	Triclinic, P1
Temperature (K)	123
a, b, c (Å)	9.0965 (3), 11.2081 (4), 15.8916 (5)
α, β, γ (°)	109.009 (2), 103.384 (2), 96.246 (2)
V (Å³)	1460.07 (9)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.71
Crystal size (mm)	0.25 × 0.25 × 0.15

Data collection
Diffractometer	Nonius KappaCCD area-detector
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	36041, 6400, 4748
R_int	0.057
(sin θ/λ)_max (Å⁻¹)	0.640

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.043, 0.112, 1.04
No. of reflections	6400
No. of parameters	407
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.71, −0.52

Computer programs: COLLECT (Nonius, 1998) and DENZO (Otwinowski & Minor, 1997), DENZO and COLLECT, DENZO, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), PLATON (Spek, 2003) and ORTEP-3 (Farrugia, 1997, SHELXL97.