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Chloro­thia­zide forms a 1:2 solvate with N,N-dimethyl­acetamide (systematic name: 6-chloro-4H-1,2,4-benzothia­diazine-7-sulfonamide 1,1-dioxide N,N-dimethyl­acetamide disolvate), C7H6ClN3O4S2·2C4H9NO. The compound crystallizes with one chloro­thia­zide and two solvent mol­ecules in the asymmetric unit, forming three intermolecular N—H...O hydrogen bonds.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807016388/at2264sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807016388/at2264Isup2.hkl
Contains datablock I

CCDC reference: 647567

Key indicators

  • Single-crystal X-ray study
  • T = 123 K
  • Mean [sigma](C-C) = 0.004 Å
  • Disorder in solvent or counterion
  • R factor = 0.044
  • wR factor = 0.098
  • Data-to-parameter ratio = 12.9

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.02 PLAT302_ALERT_4_C Anion/Solvent Disorder ......................... 25.00 Perc.
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 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 1 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 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Comment top

Chlorothiazide (CT) is a thiazide diuretic drug that is known to crystallize in at least one non-solvated form (Dupont & Dideberg, 1970; Shankland et al., 1997). The title compound, (I), was produced as part of an automated parallel crystallization study (Florence et al., 2006) of CT as part of a wider investigation that couples automated parallel crystallization with crystal structure prediction methodology to investigate the basic science underlying the solid-state diversity of CT and the related thiazide diuretic, hydrochlorothiazide (Johnston et al., 2007). The sample was identified as a novel form using multi-sample foil transmission X-ray powder diffraction analysis (Florence et al., 2003). Subsequent manual recrystallization from a saturated N,N-dimethylacetamide solution (DMA) by slow evaporation at 278 K yielded samples of (I) suitable for single-crystal X-ray diffraction (Fig. 1).

Compound (I) crystallizes with one CT and two DMA molecules in the asymmetric unit, with one of the solvent molecules (residue C) disordered over two sites.

The structure contains three N—H···O bonds (Table 1), with all available hydrogen-bond donors in CT (N3—H3N, N3—H2N and N2—H1N) forming contacts to adjacent acetyl O-atoms of DMA. Contacts 1 and 3 combine to form an R24(20) motif (Etter, 1990) between CT and DMA residue B, whilst contact 2 connects DMA residue C to CT (Fig. 2).

Related literature top

For related literature, see: Dupont & Dideberg (1970); Etter (1990); Florence et al. (2003,2006); Johnston et al. (2007); Shankland et al. (1997).

Experimental top

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

Refinement top

The three amine H atoms were found by difference synthesis and refined freely. All other H atoms were constrained to idealized geometry using riding models, with C—H = 0.98 Å and Uiso(H) = 1.5Ueq(C) for CH3 groups, and C—H =

0.95 Å and Uiso(H) = 1.2Ueq(C) for CH groups. One solvent molecule was modelled as disordered over two positions [occupancies refined to 0.58 (2):0.42 (2)] with shared C12 and C15 sites.

Structure description top

Chlorothiazide (CT) is a thiazide diuretic drug that is known to crystallize in at least one non-solvated form (Dupont & Dideberg, 1970; Shankland et al., 1997). The title compound, (I), was produced as part of an automated parallel crystallization study (Florence et al., 2006) of CT as part of a wider investigation that couples automated parallel crystallization with crystal structure prediction methodology to investigate the basic science underlying the solid-state diversity of CT and the related thiazide diuretic, hydrochlorothiazide (Johnston et al., 2007). The sample was identified as a novel form using multi-sample foil transmission X-ray powder diffraction analysis (Florence et al., 2003). Subsequent manual recrystallization from a saturated N,N-dimethylacetamide solution (DMA) by slow evaporation at 278 K yielded samples of (I) suitable for single-crystal X-ray diffraction (Fig. 1).

Compound (I) crystallizes with one CT and two DMA molecules in the asymmetric unit, with one of the solvent molecules (residue C) disordered over two sites.

The structure contains three N—H···O bonds (Table 1), with all available hydrogen-bond donors in CT (N3—H3N, N3—H2N and N2—H1N) forming contacts to adjacent acetyl O-atoms of DMA. Contacts 1 and 3 combine to form an R24(20) motif (Etter, 1990) between CT and DMA residue B, whilst contact 2 connects DMA residue C to CT (Fig. 2).

For related literature, see: Dupont & Dideberg (1970); Etter (1990); Florence et al. (2003,2006); Johnston et al. (2007); Shankland et al. (1997).

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
[Figure 1] Fig. 1. The asymmetric unit of (I), showing 50% probablility displacement ellipsoids. Minor occupancy disordered atomic sites (residue C) have been omitted for clarity.
[Figure 2] Fig. 2. The packing motif of (I), showing the centrosymmetric R24(20) motif between CT and DMA (residue B) molecules, as well as the N—H···O contact between CT and disordered DMA residue C. Hydrogen bonds are shown as dashed lines and minor disorder components have been omitted for clarity. [Symmetry codes:(i) 1 - x, 2 - y, 1 - z; (ii) 1/2 - x, 1/2 + y, 3/2 - z; (iii) 1/2 + x, 3/2 - y, -1/2 + z.]
6-chloro-2H-1,2,4-benzothiadiazine-7-sulfonamide 1,1-dioxide N,N-dimethylacetamide disolvate top
Crystal data top
C7H6ClN3O4S2·2C4H9NOF(000) = 984
Mr = 469.96Dx = 1.511 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 8879 reflections
a = 8.2037 (3) Åθ = 1.0–27.1°
b = 24.5226 (6) ŵ = 0.43 mm1
c = 10.6443 (3) ÅT = 123 K
β = 105.231 (2)°Bar, colourless
V = 2066.16 (11) Å30.25 × 0.12 × 0.06 mm
Z = 4
Data collection top
Nonius Kappa CCD area-detector
diffractometer
2579 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.094
Graphite monochromatorθmax = 26.0°, θmin = 1.7°
φ and ω scansh = 910
15173 measured reflectionsk = 3030
4061 independent reflectionsl = 1313
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.044Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.098H atoms treated by a mixture of independent and constrained refinement
S = 1.02 w = 1/[σ2(Fo2) + (0.0359P)2 + 1.0897P]
where P = (Fo2 + 2Fc2)/3
4061 reflections(Δ/σ)max = 0.002
315 parametersΔρmax = 0.34 e Å3
0 restraintsΔρmin = 0.39 e Å3
Crystal data top
C7H6ClN3O4S2·2C4H9NOV = 2066.16 (11) Å3
Mr = 469.96Z = 4
Monoclinic, P21/nMo Kα radiation
a = 8.2037 (3) ŵ = 0.43 mm1
b = 24.5226 (6) ÅT = 123 K
c = 10.6443 (3) Å0.25 × 0.12 × 0.06 mm
β = 105.231 (2)°
Data collection top
Nonius Kappa CCD area-detector
diffractometer
2579 reflections with I > 2σ(I)
15173 measured reflectionsRint = 0.094
4061 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0440 restraints
wR(F2) = 0.098H atoms treated by a mixture of independent and constrained refinement
S = 1.02Δρmax = 0.34 e Å3
4061 reflectionsΔρmin = 0.39 e Å3
315 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
xyzUiso*/UeqOcc. (<1)
Cl10.86503 (9)1.06818 (3)0.36097 (7)0.0287 (2)
S10.62335 (10)0.87377 (3)0.64178 (7)0.0265 (2)
S20.75667 (9)0.95507 (3)0.20371 (7)0.0266 (2)
O10.4740 (3)0.84724 (8)0.56543 (18)0.0371 (6)
O20.7733 (3)0.84094 (8)0.68134 (19)0.0378 (6)
O30.6779 (2)0.99953 (8)0.12360 (17)0.0321 (5)
O40.9323 (2)0.94450 (9)0.21843 (18)0.0364 (5)
N10.5850 (3)0.89908 (9)0.7715 (2)0.0275 (6)
N20.6902 (3)0.98702 (10)0.7444 (2)0.0215 (6)
N30.6539 (4)0.90121 (12)0.1483 (2)0.0287 (6)
C10.6280 (3)0.94856 (12)0.8083 (3)0.0251 (7)
H10.61360.95890.89070.030*
C20.7069 (3)0.97998 (11)0.6192 (2)0.0195 (6)
C30.6686 (3)0.93016 (10)0.5563 (2)0.0189 (6)
C40.6775 (3)0.92372 (10)0.4284 (2)0.0197 (6)
H40.64510.89000.38490.024*
C50.7329 (3)0.96583 (11)0.3640 (2)0.0197 (6)
C60.7786 (3)1.01539 (10)0.4309 (3)0.0205 (6)
C70.7605 (3)1.02315 (10)0.5543 (3)0.0203 (6)
H70.78441.05770.59530.024*
O50.3012 (2)0.90969 (8)0.15126 (19)0.0310 (5)
N40.1638 (3)0.83042 (10)0.1039 (3)0.0398 (7)
C80.0491 (4)0.91005 (12)0.0279 (3)0.0350 (8)
H8A0.07940.94850.03220.053*
H8B0.06330.90740.01240.053*
H8C0.04800.89210.11030.053*
C90.1766 (4)0.88256 (13)0.0817 (3)0.0353 (8)
C100.2902 (4)0.80452 (13)0.2124 (3)0.0485 (9)
H10A0.39860.80210.19020.073*
H10B0.25190.76780.22740.073*
H10C0.30390.82650.29140.073*
C110.0204 (4)0.79663 (14)0.0324 (3)0.0557 (11)
H11A0.04180.81600.04610.084*
H11B0.05500.78940.08820.084*
H11C0.06300.76200.00750.084*
O60.2074 (16)0.7032 (6)0.7823 (13)0.030 (2)0.582 (18)
N50.4587 (10)0.7349 (4)0.8926 (6)0.031 (2)0.582 (18)
C120.2503 (4)0.80107 (12)0.7830 (3)0.0365 (8)
H12A0.30690.81450.71890.055*0.582 (18)
H12B0.27630.82490.85940.055*0.582 (18)
H12C0.12740.80070.74400.055*0.582 (18)
H12D0.28260.81350.70540.055*0.418 (18)
H12E0.23520.83270.83510.055*0.418 (18)
H12F0.14420.78060.75660.055*0.418 (18)
C130.3049 (12)0.7419 (5)0.8214 (7)0.025 (2)0.582 (18)
C140.577 (2)0.7779 (6)0.9476 (19)0.039 (3)0.582 (18)
H14A0.53010.81320.91320.059*0.582 (18)
H14B0.68370.77170.92410.059*0.582 (18)
H14C0.59860.77781.04260.059*0.582 (18)
C150.5077 (4)0.67715 (13)0.9299 (3)0.0446 (9)
H15A0.45110.66490.99540.067*0.582 (18)
H15B0.63040.67490.96600.067*0.582 (18)
H15C0.47360.65380.85270.067*0.582 (18)
H15D0.47540.66851.01000.067*0.418 (18)
H15E0.61680.69600.95180.067*0.418 (18)
H15F0.51740.64340.88320.067*0.418 (18)
O70.248 (3)0.6938 (8)0.7573 (19)0.036 (3)0.418 (18)
N60.3880 (17)0.7667 (5)0.8636 (9)0.033 (3)0.418 (18)
C160.371 (2)0.7123 (5)0.8437 (12)0.032 (4)0.418 (18)
C170.533 (3)0.7924 (10)0.955 (3)0.063 (8)0.418 (18)
H17A0.56350.77161.03630.094*0.418 (18)
H17B0.50430.82980.97290.094*0.418 (18)
H17C0.62920.79290.91620.094*0.418 (18)
H1N0.706 (4)1.0162 (12)0.776 (3)0.031 (9)*
H2N0.697 (4)0.8701 (13)0.187 (3)0.041 (10)*
H3N0.546 (4)0.9047 (12)0.137 (3)0.040 (10)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0314 (4)0.0265 (4)0.0280 (4)0.0046 (3)0.0075 (3)0.0036 (3)
S10.0337 (5)0.0215 (4)0.0259 (4)0.0019 (4)0.0107 (4)0.0002 (3)
S20.0223 (4)0.0386 (5)0.0189 (4)0.0005 (4)0.0052 (3)0.0045 (3)
O10.0433 (14)0.0351 (12)0.0332 (12)0.0194 (11)0.0107 (11)0.0067 (10)
O20.0448 (14)0.0272 (11)0.0444 (14)0.0129 (10)0.0169 (11)0.0095 (10)
O30.0330 (13)0.0418 (12)0.0198 (11)0.0004 (10)0.0036 (9)0.0048 (9)
O40.0199 (12)0.0648 (15)0.0259 (11)0.0032 (10)0.0084 (9)0.0102 (10)
N10.0322 (15)0.0275 (14)0.0246 (13)0.0023 (12)0.0106 (11)0.0001 (11)
N20.0261 (15)0.0167 (14)0.0216 (14)0.0010 (12)0.0061 (11)0.0035 (12)
N30.0243 (18)0.0359 (17)0.0237 (14)0.0013 (14)0.0025 (13)0.0092 (13)
C10.0233 (17)0.0341 (18)0.0177 (15)0.0035 (14)0.0046 (13)0.0004 (13)
C20.0180 (16)0.0241 (16)0.0149 (14)0.0040 (13)0.0016 (12)0.0016 (12)
C30.0165 (15)0.0181 (14)0.0223 (15)0.0008 (12)0.0055 (12)0.0021 (12)
C40.0162 (16)0.0179 (15)0.0234 (15)0.0005 (12)0.0026 (12)0.0068 (12)
C50.0141 (15)0.0263 (16)0.0170 (14)0.0006 (12)0.0013 (12)0.0018 (12)
C60.0139 (15)0.0204 (15)0.0258 (16)0.0015 (12)0.0028 (12)0.0026 (12)
C70.0200 (16)0.0171 (15)0.0211 (15)0.0021 (12)0.0009 (13)0.0024 (12)
O50.0272 (12)0.0276 (11)0.0373 (12)0.0051 (10)0.0066 (10)0.0117 (10)
N40.0436 (18)0.0343 (17)0.0447 (17)0.0038 (14)0.0175 (14)0.0015 (13)
C80.036 (2)0.0411 (19)0.0276 (17)0.0008 (16)0.0078 (15)0.0015 (15)
C90.042 (2)0.035 (2)0.039 (2)0.0099 (17)0.0288 (18)0.0001 (16)
C100.049 (2)0.036 (2)0.058 (2)0.0086 (17)0.010 (2)0.0145 (17)
C110.054 (3)0.056 (2)0.057 (2)0.034 (2)0.015 (2)0.0084 (19)
O60.027 (5)0.023 (5)0.036 (4)0.004 (3)0.003 (3)0.001 (3)
N50.030 (4)0.028 (5)0.029 (3)0.013 (4)0.000 (3)0.001 (3)
C120.048 (2)0.0283 (18)0.0331 (18)0.0088 (16)0.0103 (16)0.0038 (14)
C130.031 (5)0.022 (5)0.025 (4)0.003 (5)0.014 (3)0.004 (4)
C140.043 (7)0.034 (8)0.035 (5)0.020 (6)0.001 (5)0.001 (6)
C150.038 (2)0.038 (2)0.049 (2)0.0049 (17)0.0038 (17)0.0163 (17)
O70.032 (8)0.022 (6)0.044 (8)0.002 (5)0.007 (5)0.007 (4)
N60.048 (7)0.024 (6)0.027 (4)0.008 (6)0.011 (5)0.001 (4)
C160.048 (9)0.021 (7)0.032 (7)0.004 (8)0.019 (7)0.003 (6)
C170.071 (15)0.034 (10)0.054 (12)0.005 (8)0.035 (10)0.007 (8)
Geometric parameters (Å, º) top
Cl1—C61.735 (3)C10—H10A0.9800
S1—O11.436 (2)C10—H10B0.9800
S1—O21.437 (2)C10—H10C0.9800
S1—N11.619 (2)C11—H11A0.9800
S1—C31.748 (3)C11—H11B0.9800
S2—O31.4297 (19)C11—H11C0.9800
S2—O41.431 (2)O6—C131.24 (2)
S2—N31.595 (3)N5—C131.300 (16)
S2—C51.786 (3)N5—C141.45 (2)
N1—C11.295 (3)N5—C151.498 (11)
N2—C11.339 (3)C12—C131.541 (12)
N2—C21.386 (3)C12—H12A0.9783
N2—H1N0.79 (3)C12—H12B0.9770
N3—H2N0.89 (3)C12—H12C0.9843
N3—H3N0.87 (3)C12—H12D0.9800
C1—H10.9500C12—H12E0.9800
C2—C31.389 (3)C12—H12F0.9800
C2—C71.397 (4)C14—H14A0.9800
C3—C41.392 (4)C14—H14B0.9800
C4—C51.381 (4)C14—H14C0.9800
C4—H40.9500C15—H15A0.9800
C5—C61.409 (4)C15—H15B0.9800
C6—C71.373 (4)C15—H15C0.9800
C7—H70.9500C15—H15D0.9800
O5—C91.280 (4)C15—H15E0.9800
N4—C91.310 (4)C15—H15F0.9801
N4—C111.476 (4)O7—C161.26 (3)
N4—C101.477 (4)N6—C161.35 (2)
C8—C91.506 (4)N6—C171.47 (3)
C8—H8A0.9800C17—H17A0.9800
C8—H8B0.9800C17—H17B0.9800
C8—H8C0.9800C17—H17C0.9800
O1—S1—O2116.70 (13)N4—C9—C8120.3 (3)
O1—S1—N1109.17 (13)N4—C10—H10A109.5
O2—S1—N1107.95 (12)N4—C10—H10B109.5
O1—S1—C3109.28 (12)H10A—C10—H10B109.5
O2—S1—C3108.26 (13)N4—C10—H10C109.5
N1—S1—C3104.83 (12)H10A—C10—H10C109.5
O3—S2—O4119.20 (13)H10B—C10—H10C109.5
O3—S2—N3107.38 (14)N4—C11—H11A109.5
O4—S2—N3108.05 (15)N4—C11—H11B109.5
O3—S2—C5108.13 (12)H11A—C11—H11B109.5
O4—S2—C5106.33 (12)N4—C11—H11C109.5
N3—S2—C5107.20 (13)H11A—C11—H11C109.5
C1—N1—S1121.2 (2)H11B—C11—H11C109.5
C1—N2—C2123.2 (2)C13—N5—C14125.8 (14)
C1—N2—H1N117 (2)C13—N5—C15115.5 (12)
C2—N2—H1N119 (2)C14—N5—C15118.4 (8)
S2—N3—H2N115 (2)C13—C12—H12A110.1
S2—N3—H3N113 (2)C13—C12—H12B110.9
H2N—N3—H3N115 (3)H12A—C12—H12B109.9
N1—C1—N2128.1 (3)C13—C12—H12C107.3
N1—C1—H1116.0H12A—C12—H12C109.3
N2—C1—H1116.0H12B—C12—H12C109.4
N2—C2—C3120.4 (2)C13—C12—H12D113.1
N2—C2—C7120.3 (2)C13—C12—H12E131.8
C3—C2—C7119.3 (2)H12D—C12—H12E109.5
C2—C3—C4120.5 (2)C13—C12—H12F76.6
C2—C3—S1119.8 (2)H12D—C12—H12F109.5
C4—C3—S1119.50 (19)H12E—C12—H12F109.5
C5—C4—C3120.7 (2)O6—C13—N5122.4 (15)
C5—C4—H4119.7O6—C13—C12121.0 (9)
C3—C4—H4119.7N5—C13—C12116.6 (12)
C4—C5—C6118.2 (2)N5—C15—H15A109.5
C4—C5—S2119.8 (2)N5—C15—H15B109.5
C6—C5—S2121.9 (2)H15A—C15—H15B109.5
C7—C6—C5121.5 (2)N5—C15—H15C109.5
C7—C6—Cl1117.8 (2)H15A—C15—H15C109.5
C5—C6—Cl1120.7 (2)H15B—C15—H15C109.5
C6—C7—C2119.7 (2)N5—C15—H15D108.7
C6—C7—H7120.2N5—C15—H15E77.3
C2—C7—H7120.2H15A—C15—H15E123.3
C9—N4—C11123.1 (3)N5—C15—H15F135.8
C9—N4—C10119.2 (3)H15D—C15—H15F109.6
C11—N4—C10117.5 (3)H15E—C15—H15F109.2
C9—C8—H8A109.5C16—N6—C17124.0 (18)
C9—C8—H8B109.5O7—C16—N6120 (2)
H8A—C8—H8B109.5N6—C17—H17A109.5
C9—C8—H8C109.5N6—C17—H17B109.6
H8A—C8—H8C109.5H17A—C17—H17B109.5
H8B—C8—H8C109.5N6—C17—H17C109.2
O5—C9—N4119.5 (3)H17A—C17—H17C109.5
O5—C9—C8120.2 (3)H17B—C17—H17C109.5
O1—S1—N1—C1132.9 (2)O4—S2—C5—C498.6 (2)
O2—S1—N1—C199.3 (2)N3—S2—C5—C416.8 (3)
C3—S1—N1—C115.9 (3)O3—S2—C5—C651.5 (2)
S1—N1—C1—N27.4 (4)O4—S2—C5—C677.7 (2)
C2—N2—C1—N15.0 (5)N3—S2—C5—C6167.0 (2)
C1—N2—C2—C34.2 (4)C4—C5—C6—C73.4 (4)
C1—N2—C2—C7175.1 (3)S2—C5—C6—C7179.7 (2)
N2—C2—C3—C4177.0 (2)C4—C5—C6—Cl1174.9 (2)
C7—C2—C3—C42.3 (4)S2—C5—C6—Cl11.4 (3)
N2—C2—C3—S17.6 (4)C5—C6—C7—C24.5 (4)
C7—C2—C3—S1173.1 (2)Cl1—C6—C7—C2173.8 (2)
O1—S1—C3—C2133.0 (2)N2—C2—C7—C6179.1 (2)
O2—S1—C3—C298.9 (2)C3—C2—C7—C61.6 (4)
N1—S1—C3—C216.1 (3)C11—N4—C9—O5177.2 (3)
O1—S1—C3—C451.5 (2)C10—N4—C9—O52.3 (4)
O2—S1—C3—C476.6 (2)C11—N4—C9—C84.9 (4)
N1—S1—C3—C4168.4 (2)C10—N4—C9—C8179.7 (3)
C2—C3—C4—C53.4 (4)C14—N5—C13—O6176.7 (11)
S1—C3—C4—C5172.1 (2)C15—N5—C13—O63.0 (10)
C3—C4—C5—C60.5 (4)C14—N5—C13—C125.5 (12)
C3—C4—C5—S2175.8 (2)C15—N5—C13—C12179.2 (4)
O3—S2—C5—C4132.3 (2)C17—N6—C16—O7175.2 (17)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N3—H3N···O50.87 (3)2.06 (3)2.909 (4)168 (3)
N3—H2N···O6i0.89 (3)2.05 (3)2.906 (14)159 (3)
N2—H1N···O5ii0.79 (3)1.98 (3)2.759 (3)170 (3)
N3—H2N···O7i0.89 (3)1.74 (4)2.628 (18)171 (3)
Symmetry codes: (i) x+1/2, y+3/2, z1/2; (ii) x+1, y+2, z+1.

Experimental details

Crystal data
Chemical formulaC7H6ClN3O4S2·2C4H9NO
Mr469.96
Crystal system, space groupMonoclinic, P21/n
Temperature (K)123
a, b, c (Å)8.2037 (3), 24.5226 (6), 10.6443 (3)
β (°) 105.231 (2)
V3)2066.16 (11)
Z4
Radiation typeMo Kα
µ (mm1)0.43
Crystal size (mm)0.25 × 0.12 × 0.06
Data collection
DiffractometerNonius Kappa CCD area-detector
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
15173, 4061, 2579
Rint0.094
(sin θ/λ)max1)0.617
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.044, 0.098, 1.02
No. of reflections4061
No. of parameters315
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.34, 0.39

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.

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N3—H3N···O50.87 (3)2.06 (3)2.909 (4)168 (3)
N3—H2N···O6i0.89 (3)2.05 (3)2.906 (14)159 (3)
N2—H1N···O5ii0.79 (3)1.98 (3)2.759 (3)170 (3)
N3—H2N···O7i0.89 (3)1.74 (4)2.628 (18)171 (3)
Symmetry codes: (i) x+1/2, y+3/2, z1/2; (ii) x+1, y+2, z+1.
 

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