Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807016388/at2264sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807016388/at2264Isup2.hkl |
CCDC reference: 647567
Key indicators
- Single-crystal X-ray study
- T = 123 K
- Mean (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
For related literature, see: Dupont & Dideberg (1970); Etter (1990); Florence et al. (2003,2006); Johnston et al. (2007); Shankland et al. (1997).
A single-crystal sample of the title compound, (I), was recrystallized from a saturated dimethylacetamide solution by isothermal solvent evaporation at 278 K.
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.
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).
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.
C7H6ClN3O4S2·2C4H9NO | F(000) = 984 |
Mr = 469.96 | Dx = 1.511 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 8879 reflections |
a = 8.2037 (3) Å | θ = 1.0–27.1° |
b = 24.5226 (6) Å | µ = 0.43 mm−1 |
c = 10.6443 (3) Å | T = 123 K |
β = 105.231 (2)° | Bar, colourless |
V = 2066.16 (11) Å3 | 0.25 × 0.12 × 0.06 mm |
Z = 4 |
Nonius Kappa CCD area-detector diffractometer | 2579 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.094 |
Graphite monochromator | θmax = 26.0°, θmin = 1.7° |
φ and ω scans | h = −9→10 |
15173 measured reflections | k = −30→30 |
4061 independent reflections | l = −13→13 |
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)] = 0.044 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.098 | H 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 parameters | Δρmax = 0.34 e Å−3 |
0 restraints | Δρmin = −0.39 e Å−3 |
C7H6ClN3O4S2·2C4H9NO | V = 2066.16 (11) Å3 |
Mr = 469.96 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 8.2037 (3) Å | µ = 0.43 mm−1 |
b = 24.5226 (6) Å | T = 123 K |
c = 10.6443 (3) Å | 0.25 × 0.12 × 0.06 mm |
β = 105.231 (2)° |
Nonius Kappa CCD area-detector diffractometer | 2579 reflections with I > 2σ(I) |
15173 measured reflections | Rint = 0.094 |
4061 independent reflections |
R[F2 > 2σ(F2)] = 0.044 | 0 restraints |
wR(F2) = 0.098 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.02 | Δρmax = 0.34 e Å−3 |
4061 reflections | Δρmin = −0.39 e Å−3 |
315 parameters |
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. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
Cl1 | 0.86503 (9) | 1.06818 (3) | 0.36097 (7) | 0.0287 (2) | |
S1 | 0.62335 (10) | 0.87377 (3) | 0.64178 (7) | 0.0265 (2) | |
S2 | 0.75667 (9) | 0.95507 (3) | 0.20371 (7) | 0.0266 (2) | |
O1 | 0.4740 (3) | 0.84724 (8) | 0.56543 (18) | 0.0371 (6) | |
O2 | 0.7733 (3) | 0.84094 (8) | 0.68134 (19) | 0.0378 (6) | |
O3 | 0.6779 (2) | 0.99953 (8) | 0.12360 (17) | 0.0321 (5) | |
O4 | 0.9323 (2) | 0.94450 (9) | 0.21843 (18) | 0.0364 (5) | |
N1 | 0.5850 (3) | 0.89908 (9) | 0.7715 (2) | 0.0275 (6) | |
N2 | 0.6902 (3) | 0.98702 (10) | 0.7444 (2) | 0.0215 (6) | |
N3 | 0.6539 (4) | 0.90121 (12) | 0.1483 (2) | 0.0287 (6) | |
C1 | 0.6280 (3) | 0.94856 (12) | 0.8083 (3) | 0.0251 (7) | |
H1 | 0.6136 | 0.9589 | 0.8907 | 0.030* | |
C2 | 0.7069 (3) | 0.97998 (11) | 0.6192 (2) | 0.0195 (6) | |
C3 | 0.6686 (3) | 0.93016 (10) | 0.5563 (2) | 0.0189 (6) | |
C4 | 0.6775 (3) | 0.92372 (10) | 0.4284 (2) | 0.0197 (6) | |
H4 | 0.6451 | 0.8900 | 0.3849 | 0.024* | |
C5 | 0.7329 (3) | 0.96583 (11) | 0.3640 (2) | 0.0197 (6) | |
C6 | 0.7786 (3) | 1.01539 (10) | 0.4309 (3) | 0.0205 (6) | |
C7 | 0.7605 (3) | 1.02315 (10) | 0.5543 (3) | 0.0203 (6) | |
H7 | 0.7844 | 1.0577 | 0.5953 | 0.024* | |
O5 | 0.3012 (2) | 0.90969 (8) | 0.15126 (19) | 0.0310 (5) | |
N4 | 0.1638 (3) | 0.83042 (10) | 0.1039 (3) | 0.0398 (7) | |
C8 | 0.0491 (4) | 0.91005 (12) | −0.0279 (3) | 0.0350 (8) | |
H8A | 0.0794 | 0.9485 | −0.0322 | 0.053* | |
H8B | −0.0633 | 0.9074 | −0.0124 | 0.053* | |
H8C | 0.0480 | 0.8921 | −0.1103 | 0.053* | |
C9 | 0.1766 (4) | 0.88256 (13) | 0.0817 (3) | 0.0353 (8) | |
C10 | 0.2902 (4) | 0.80452 (13) | 0.2124 (3) | 0.0485 (9) | |
H10A | 0.3986 | 0.8021 | 0.1902 | 0.073* | |
H10B | 0.2519 | 0.7678 | 0.2274 | 0.073* | |
H10C | 0.3039 | 0.8265 | 0.2914 | 0.073* | |
C11 | 0.0204 (4) | 0.79663 (14) | 0.0324 (3) | 0.0557 (11) | |
H11A | −0.0418 | 0.8160 | −0.0461 | 0.084* | |
H11B | −0.0550 | 0.7894 | 0.0882 | 0.084* | |
H11C | 0.0630 | 0.7620 | 0.0075 | 0.084* | |
O6 | 0.2074 (16) | 0.7032 (6) | 0.7823 (13) | 0.030 (2) | 0.582 (18) |
N5 | 0.4587 (10) | 0.7349 (4) | 0.8926 (6) | 0.031 (2) | 0.582 (18) |
C12 | 0.2503 (4) | 0.80107 (12) | 0.7830 (3) | 0.0365 (8) | |
H12A | 0.3069 | 0.8145 | 0.7189 | 0.055* | 0.582 (18) |
H12B | 0.2763 | 0.8249 | 0.8594 | 0.055* | 0.582 (18) |
H12C | 0.1274 | 0.8007 | 0.7440 | 0.055* | 0.582 (18) |
H12D | 0.2826 | 0.8135 | 0.7054 | 0.055* | 0.418 (18) |
H12E | 0.2352 | 0.8327 | 0.8351 | 0.055* | 0.418 (18) |
H12F | 0.1442 | 0.7806 | 0.7566 | 0.055* | 0.418 (18) |
C13 | 0.3049 (12) | 0.7419 (5) | 0.8214 (7) | 0.025 (2) | 0.582 (18) |
C14 | 0.577 (2) | 0.7779 (6) | 0.9476 (19) | 0.039 (3) | 0.582 (18) |
H14A | 0.5301 | 0.8132 | 0.9132 | 0.059* | 0.582 (18) |
H14B | 0.6837 | 0.7717 | 0.9241 | 0.059* | 0.582 (18) |
H14C | 0.5986 | 0.7778 | 1.0426 | 0.059* | 0.582 (18) |
C15 | 0.5077 (4) | 0.67715 (13) | 0.9299 (3) | 0.0446 (9) | |
H15A | 0.4511 | 0.6649 | 0.9954 | 0.067* | 0.582 (18) |
H15B | 0.6304 | 0.6749 | 0.9660 | 0.067* | 0.582 (18) |
H15C | 0.4736 | 0.6538 | 0.8527 | 0.067* | 0.582 (18) |
H15D | 0.4754 | 0.6685 | 1.0100 | 0.067* | 0.418 (18) |
H15E | 0.6168 | 0.6960 | 0.9518 | 0.067* | 0.418 (18) |
H15F | 0.5174 | 0.6434 | 0.8832 | 0.067* | 0.418 (18) |
O7 | 0.248 (3) | 0.6938 (8) | 0.7573 (19) | 0.036 (3) | 0.418 (18) |
N6 | 0.3880 (17) | 0.7667 (5) | 0.8636 (9) | 0.033 (3) | 0.418 (18) |
C16 | 0.371 (2) | 0.7123 (5) | 0.8437 (12) | 0.032 (4) | 0.418 (18) |
C17 | 0.533 (3) | 0.7924 (10) | 0.955 (3) | 0.063 (8) | 0.418 (18) |
H17A | 0.5635 | 0.7716 | 1.0363 | 0.094* | 0.418 (18) |
H17B | 0.5043 | 0.8298 | 0.9729 | 0.094* | 0.418 (18) |
H17C | 0.6292 | 0.7929 | 0.9162 | 0.094* | 0.418 (18) |
H1N | 0.706 (4) | 1.0162 (12) | 0.776 (3) | 0.031 (9)* | |
H2N | 0.697 (4) | 0.8701 (13) | 0.187 (3) | 0.041 (10)* | |
H3N | 0.546 (4) | 0.9047 (12) | 0.137 (3) | 0.040 (10)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.0314 (4) | 0.0265 (4) | 0.0280 (4) | −0.0046 (3) | 0.0075 (3) | 0.0036 (3) |
S1 | 0.0337 (5) | 0.0215 (4) | 0.0259 (4) | −0.0019 (4) | 0.0107 (4) | −0.0002 (3) |
S2 | 0.0223 (4) | 0.0386 (5) | 0.0189 (4) | −0.0005 (4) | 0.0052 (3) | −0.0045 (3) |
O1 | 0.0433 (14) | 0.0351 (12) | 0.0332 (12) | −0.0194 (11) | 0.0107 (11) | −0.0067 (10) |
O2 | 0.0448 (14) | 0.0272 (11) | 0.0444 (14) | 0.0129 (10) | 0.0169 (11) | 0.0095 (10) |
O3 | 0.0330 (13) | 0.0418 (12) | 0.0198 (11) | 0.0004 (10) | 0.0036 (9) | 0.0048 (9) |
O4 | 0.0199 (12) | 0.0648 (15) | 0.0259 (11) | 0.0032 (10) | 0.0084 (9) | −0.0102 (10) |
N1 | 0.0322 (15) | 0.0275 (14) | 0.0246 (13) | −0.0023 (12) | 0.0106 (11) | −0.0001 (11) |
N2 | 0.0261 (15) | 0.0167 (14) | 0.0216 (14) | 0.0010 (12) | 0.0061 (11) | −0.0035 (12) |
N3 | 0.0243 (18) | 0.0359 (17) | 0.0237 (14) | 0.0013 (14) | 0.0025 (13) | −0.0092 (13) |
C1 | 0.0233 (17) | 0.0341 (18) | 0.0177 (15) | 0.0035 (14) | 0.0046 (13) | 0.0004 (13) |
C2 | 0.0180 (16) | 0.0241 (16) | 0.0149 (14) | 0.0040 (13) | 0.0016 (12) | −0.0016 (12) |
C3 | 0.0165 (15) | 0.0181 (14) | 0.0223 (15) | 0.0008 (12) | 0.0055 (12) | −0.0021 (12) |
C4 | 0.0162 (16) | 0.0179 (15) | 0.0234 (15) | 0.0005 (12) | 0.0026 (12) | −0.0068 (12) |
C5 | 0.0141 (15) | 0.0263 (16) | 0.0170 (14) | −0.0006 (12) | 0.0013 (12) | −0.0018 (12) |
C6 | 0.0139 (15) | 0.0204 (15) | 0.0258 (16) | 0.0015 (12) | 0.0028 (12) | 0.0026 (12) |
C7 | 0.0200 (16) | 0.0171 (15) | 0.0211 (15) | 0.0021 (12) | 0.0009 (13) | −0.0024 (12) |
O5 | 0.0272 (12) | 0.0276 (11) | 0.0373 (12) | −0.0051 (10) | 0.0066 (10) | −0.0117 (10) |
N4 | 0.0436 (18) | 0.0343 (17) | 0.0447 (17) | −0.0038 (14) | 0.0175 (14) | −0.0015 (13) |
C8 | 0.036 (2) | 0.0411 (19) | 0.0276 (17) | 0.0008 (16) | 0.0078 (15) | 0.0015 (15) |
C9 | 0.042 (2) | 0.035 (2) | 0.039 (2) | 0.0099 (17) | 0.0288 (18) | −0.0001 (16) |
C10 | 0.049 (2) | 0.036 (2) | 0.058 (2) | 0.0086 (17) | 0.010 (2) | 0.0145 (17) |
C11 | 0.054 (3) | 0.056 (2) | 0.057 (2) | −0.034 (2) | 0.015 (2) | −0.0084 (19) |
O6 | 0.027 (5) | 0.023 (5) | 0.036 (4) | −0.004 (3) | 0.003 (3) | 0.001 (3) |
N5 | 0.030 (4) | 0.028 (5) | 0.029 (3) | −0.013 (4) | 0.000 (3) | −0.001 (3) |
C12 | 0.048 (2) | 0.0283 (18) | 0.0331 (18) | 0.0088 (16) | 0.0103 (16) | 0.0038 (14) |
C13 | 0.031 (5) | 0.022 (5) | 0.025 (4) | −0.003 (5) | 0.014 (3) | −0.004 (4) |
C14 | 0.043 (7) | 0.034 (8) | 0.035 (5) | −0.020 (6) | 0.001 (5) | 0.001 (6) |
C15 | 0.038 (2) | 0.038 (2) | 0.049 (2) | 0.0049 (17) | −0.0038 (17) | 0.0163 (17) |
O7 | 0.032 (8) | 0.022 (6) | 0.044 (8) | −0.002 (5) | −0.007 (5) | −0.007 (4) |
N6 | 0.048 (7) | 0.024 (6) | 0.027 (4) | −0.008 (6) | 0.011 (5) | 0.001 (4) |
C16 | 0.048 (9) | 0.021 (7) | 0.032 (7) | −0.004 (8) | 0.019 (7) | −0.003 (6) |
C17 | 0.071 (15) | 0.034 (10) | 0.054 (12) | −0.005 (8) | −0.035 (10) | 0.007 (8) |
Cl1—C6 | 1.735 (3) | C10—H10A | 0.9800 |
S1—O1 | 1.436 (2) | C10—H10B | 0.9800 |
S1—O2 | 1.437 (2) | C10—H10C | 0.9800 |
S1—N1 | 1.619 (2) | C11—H11A | 0.9800 |
S1—C3 | 1.748 (3) | C11—H11B | 0.9800 |
S2—O3 | 1.4297 (19) | C11—H11C | 0.9800 |
S2—O4 | 1.431 (2) | O6—C13 | 1.24 (2) |
S2—N3 | 1.595 (3) | N5—C13 | 1.300 (16) |
S2—C5 | 1.786 (3) | N5—C14 | 1.45 (2) |
N1—C1 | 1.295 (3) | N5—C15 | 1.498 (11) |
N2—C1 | 1.339 (3) | C12—C13 | 1.541 (12) |
N2—C2 | 1.386 (3) | C12—H12A | 0.9783 |
N2—H1N | 0.79 (3) | C12—H12B | 0.9770 |
N3—H2N | 0.89 (3) | C12—H12C | 0.9843 |
N3—H3N | 0.87 (3) | C12—H12D | 0.9800 |
C1—H1 | 0.9500 | C12—H12E | 0.9800 |
C2—C3 | 1.389 (3) | C12—H12F | 0.9800 |
C2—C7 | 1.397 (4) | C14—H14A | 0.9800 |
C3—C4 | 1.392 (4) | C14—H14B | 0.9800 |
C4—C5 | 1.381 (4) | C14—H14C | 0.9800 |
C4—H4 | 0.9500 | C15—H15A | 0.9800 |
C5—C6 | 1.409 (4) | C15—H15B | 0.9800 |
C6—C7 | 1.373 (4) | C15—H15C | 0.9800 |
C7—H7 | 0.9500 | C15—H15D | 0.9800 |
O5—C9 | 1.280 (4) | C15—H15E | 0.9800 |
N4—C9 | 1.310 (4) | C15—H15F | 0.9801 |
N4—C11 | 1.476 (4) | O7—C16 | 1.26 (3) |
N4—C10 | 1.477 (4) | N6—C16 | 1.35 (2) |
C8—C9 | 1.506 (4) | N6—C17 | 1.47 (3) |
C8—H8A | 0.9800 | C17—H17A | 0.9800 |
C8—H8B | 0.9800 | C17—H17B | 0.9800 |
C8—H8C | 0.9800 | C17—H17C | 0.9800 |
O1—S1—O2 | 116.70 (13) | N4—C9—C8 | 120.3 (3) |
O1—S1—N1 | 109.17 (13) | N4—C10—H10A | 109.5 |
O2—S1—N1 | 107.95 (12) | N4—C10—H10B | 109.5 |
O1—S1—C3 | 109.28 (12) | H10A—C10—H10B | 109.5 |
O2—S1—C3 | 108.26 (13) | N4—C10—H10C | 109.5 |
N1—S1—C3 | 104.83 (12) | H10A—C10—H10C | 109.5 |
O3—S2—O4 | 119.20 (13) | H10B—C10—H10C | 109.5 |
O3—S2—N3 | 107.38 (14) | N4—C11—H11A | 109.5 |
O4—S2—N3 | 108.05 (15) | N4—C11—H11B | 109.5 |
O3—S2—C5 | 108.13 (12) | H11A—C11—H11B | 109.5 |
O4—S2—C5 | 106.33 (12) | N4—C11—H11C | 109.5 |
N3—S2—C5 | 107.20 (13) | H11A—C11—H11C | 109.5 |
C1—N1—S1 | 121.2 (2) | H11B—C11—H11C | 109.5 |
C1—N2—C2 | 123.2 (2) | C13—N5—C14 | 125.8 (14) |
C1—N2—H1N | 117 (2) | C13—N5—C15 | 115.5 (12) |
C2—N2—H1N | 119 (2) | C14—N5—C15 | 118.4 (8) |
S2—N3—H2N | 115 (2) | C13—C12—H12A | 110.1 |
S2—N3—H3N | 113 (2) | C13—C12—H12B | 110.9 |
H2N—N3—H3N | 115 (3) | H12A—C12—H12B | 109.9 |
N1—C1—N2 | 128.1 (3) | C13—C12—H12C | 107.3 |
N1—C1—H1 | 116.0 | H12A—C12—H12C | 109.3 |
N2—C1—H1 | 116.0 | H12B—C12—H12C | 109.4 |
N2—C2—C3 | 120.4 (2) | C13—C12—H12D | 113.1 |
N2—C2—C7 | 120.3 (2) | C13—C12—H12E | 131.8 |
C3—C2—C7 | 119.3 (2) | H12D—C12—H12E | 109.5 |
C2—C3—C4 | 120.5 (2) | C13—C12—H12F | 76.6 |
C2—C3—S1 | 119.8 (2) | H12D—C12—H12F | 109.5 |
C4—C3—S1 | 119.50 (19) | H12E—C12—H12F | 109.5 |
C5—C4—C3 | 120.7 (2) | O6—C13—N5 | 122.4 (15) |
C5—C4—H4 | 119.7 | O6—C13—C12 | 121.0 (9) |
C3—C4—H4 | 119.7 | N5—C13—C12 | 116.6 (12) |
C4—C5—C6 | 118.2 (2) | N5—C15—H15A | 109.5 |
C4—C5—S2 | 119.8 (2) | N5—C15—H15B | 109.5 |
C6—C5—S2 | 121.9 (2) | H15A—C15—H15B | 109.5 |
C7—C6—C5 | 121.5 (2) | N5—C15—H15C | 109.5 |
C7—C6—Cl1 | 117.8 (2) | H15A—C15—H15C | 109.5 |
C5—C6—Cl1 | 120.7 (2) | H15B—C15—H15C | 109.5 |
C6—C7—C2 | 119.7 (2) | N5—C15—H15D | 108.7 |
C6—C7—H7 | 120.2 | N5—C15—H15E | 77.3 |
C2—C7—H7 | 120.2 | H15A—C15—H15E | 123.3 |
C9—N4—C11 | 123.1 (3) | N5—C15—H15F | 135.8 |
C9—N4—C10 | 119.2 (3) | H15D—C15—H15F | 109.6 |
C11—N4—C10 | 117.5 (3) | H15E—C15—H15F | 109.2 |
C9—C8—H8A | 109.5 | C16—N6—C17 | 124.0 (18) |
C9—C8—H8B | 109.5 | O7—C16—N6 | 120 (2) |
H8A—C8—H8B | 109.5 | N6—C17—H17A | 109.5 |
C9—C8—H8C | 109.5 | N6—C17—H17B | 109.6 |
H8A—C8—H8C | 109.5 | H17A—C17—H17B | 109.5 |
H8B—C8—H8C | 109.5 | N6—C17—H17C | 109.2 |
O5—C9—N4 | 119.5 (3) | H17A—C17—H17C | 109.5 |
O5—C9—C8 | 120.2 (3) | H17B—C17—H17C | 109.5 |
O1—S1—N1—C1 | −132.9 (2) | O4—S2—C5—C4 | −98.6 (2) |
O2—S1—N1—C1 | 99.3 (2) | N3—S2—C5—C4 | 16.8 (3) |
C3—S1—N1—C1 | −15.9 (3) | O3—S2—C5—C6 | −51.5 (2) |
S1—N1—C1—N2 | 7.4 (4) | O4—S2—C5—C6 | 77.7 (2) |
C2—N2—C1—N1 | 5.0 (5) | N3—S2—C5—C6 | −167.0 (2) |
C1—N2—C2—C3 | −4.2 (4) | C4—C5—C6—C7 | −3.4 (4) |
C1—N2—C2—C7 | 175.1 (3) | S2—C5—C6—C7 | −179.7 (2) |
N2—C2—C3—C4 | 177.0 (2) | C4—C5—C6—Cl1 | 174.9 (2) |
C7—C2—C3—C4 | −2.3 (4) | S2—C5—C6—Cl1 | −1.4 (3) |
N2—C2—C3—S1 | −7.6 (4) | C5—C6—C7—C2 | 4.5 (4) |
C7—C2—C3—S1 | 173.1 (2) | Cl1—C6—C7—C2 | −173.8 (2) |
O1—S1—C3—C2 | 133.0 (2) | N2—C2—C7—C6 | 179.1 (2) |
O2—S1—C3—C2 | −98.9 (2) | C3—C2—C7—C6 | −1.6 (4) |
N1—S1—C3—C2 | 16.1 (3) | C11—N4—C9—O5 | 177.2 (3) |
O1—S1—C3—C4 | −51.5 (2) | C10—N4—C9—O5 | 2.3 (4) |
O2—S1—C3—C4 | 76.6 (2) | C11—N4—C9—C8 | −4.9 (4) |
N1—S1—C3—C4 | −168.4 (2) | C10—N4—C9—C8 | −179.7 (3) |
C2—C3—C4—C5 | 3.4 (4) | C14—N5—C13—O6 | −176.7 (11) |
S1—C3—C4—C5 | −172.1 (2) | C15—N5—C13—O6 | −3.0 (10) |
C3—C4—C5—C6 | −0.5 (4) | C14—N5—C13—C12 | 5.5 (12) |
C3—C4—C5—S2 | 175.8 (2) | C15—N5—C13—C12 | 179.2 (4) |
O3—S2—C5—C4 | 132.3 (2) | C17—N6—C16—O7 | −175.2 (17) |
D—H···A | D—H | H···A | D···A | D—H···A |
N3—H3N···O5 | 0.87 (3) | 2.06 (3) | 2.909 (4) | 168 (3) |
N3—H2N···O6i | 0.89 (3) | 2.05 (3) | 2.906 (14) | 159 (3) |
N2—H1N···O5ii | 0.79 (3) | 1.98 (3) | 2.759 (3) | 170 (3) |
N3—H2N···O7i | 0.89 (3) | 1.74 (4) | 2.628 (18) | 171 (3) |
Symmetry codes: (i) x+1/2, −y+3/2, z−1/2; (ii) −x+1, −y+2, −z+1. |
Experimental details
Crystal data | |
Chemical formula | C7H6ClN3O4S2·2C4H9NO |
Mr | 469.96 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 123 |
a, b, c (Å) | 8.2037 (3), 24.5226 (6), 10.6443 (3) |
β (°) | 105.231 (2) |
V (Å3) | 2066.16 (11) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.43 |
Crystal size (mm) | 0.25 × 0.12 × 0.06 |
Data collection | |
Diffractometer | Nonius Kappa CCD area-detector |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 15173, 4061, 2579 |
Rint | 0.094 |
(sin θ/λ)max (Å−1) | 0.617 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.044, 0.098, 1.02 |
No. of reflections | 4061 |
No. of parameters | 315 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 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.
D—H···A | D—H | H···A | D···A | D—H···A |
N3—H3N···O5 | 0.87 (3) | 2.06 (3) | 2.909 (4) | 168 (3) |
N3—H2N···O6i | 0.89 (3) | 2.05 (3) | 2.906 (14) | 159 (3) |
N2—H1N···O5ii | 0.79 (3) | 1.98 (3) | 2.759 (3) | 170 (3) |
N3—H2N···O7i | 0.89 (3) | 1.74 (4) | 2.628 (18) | 171 (3) |
Symmetry codes: (i) x+1/2, −y+3/2, z−1/2; (ii) −x+1, −y+2, −z+1. |
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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).