Hydrochlorothiazide dimethyl sulfoxide solvate

Hydrochlorothiazide (HCT) is a thiazide diuretic which is known to crystallize in at least two non-solvated forms; form I (Dupont & Dideberg, 1972) and form II (Florence et al., 2005). The dimethyl sulfoxide (DMSO) solvate, (I), was produced during an automated parallel crystallization polymorph search on HCT. The sample was identified as a new form using multisample X-ray powder diffraction analysis of all recrystallized samples (Florence et al., 2003). Subsequent manual recrystallization by slow evaporation of a saturated DMSO solution at 278 K yielded samples of (I) suitable for single-crystal X-ray analysis (Fig. 1).


Comment
Hydrochlorothiazide (HCT) is a thiazide diuretic which is known to crystallize in at least two non-solvated forms; form I (Dupont & Dideberg, 1972) and form II (Florence et al., 2005). The dimethyl sulfoxide (DMSO) solvate, (I), was produced during an automated parallel crystallization polymorph search on HCT. The sample was identified as a new form using multisample X-ray powder diffraction analysis of all recrystallized samples (Florence et al., 2003). Subsequent manual recrystallization by slow evaporation of a saturated DMSO solution at 278 K yielded samples of (I) suitable for single-crystal X-ray analysis (Fig. 1).
H atoms bonded to N atoms were found in difference maps and refined isotropically, but all other H atoms were constrained to idealized geometry using a riding model; U iso (H) = 1.2U eq (C) and C-H = 0.95 (CH group) or 0.99 Å (CH 2 groups).

Figure 3
The R 2 2 (8) hydrogen-bonded motif in the crystal structure of (I). Control

Special details
Experimental. Although no formal absorption correction was applied, the standard Kappa CCD methodology involves collecting a large number of redundant reflections and processing via SCALEPACK. This effectively introduces a multiscan type correction suitable for weakly absorbing molecules.

sup-2
Acta Cryst. (2006). E62, o2288-o2290 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 F 2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F 2 , conventional R-factors R are based on F, with F set to zero for negative F 2 . The threshold expression of F 2 > σ(F 2 ) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F 2 are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger.