Tizoxanide pyridine monosolvate.

IN THE TITLE COMPOUND [SYSTEMATIC NAME: 2-hy-droxy-N-(5-nitro-1,3-thia-zol-2-yl)benzamide pyridine monosolvate], C(10)H(7)N(3)O(4)S·C(5)H(5)N, the dihedral angle between the pyridine and benzamide rings is 80.55 (7)°. An intamolecular O-H⋯N hydrogen bond occurs in the tizoxanide. In the crystal, the components are linked by an O-H⋯N hydrogen bond, forming a zigzag chain along the c axis. Aromatic π-π inter-actions between inversion-related pyridine rings [centroid-centroid distance = 3.803 (6) Å] are also observed.

Related literature

For the biological activity of tizoxanide, see: Rao et al. (2009 ▶); Gargala et al. (2000 ▶); Dubreuil et al. (1996 ▶); Ashton et al. (2010 ▶); Korba, Elazar et al. (2008 ▶); Zhao et al. (2010 ▶). For related structures and background to the bioactivity of tizoxanide, see: Pankuch & Appelbaum (2006 ▶); Stettler et al. (2003 ▶); Broekhuysen et al. (2000 ▶). For details on experimental methods used to obtain this form and analogues, see: Navarrete-Vazquez et al. (2011 ▶). For a pyridine-solvated forms, see: Dong et al. (2011 ▶). For additional literature on related tizoxanide thiazolide compounds, see: Megraud et al. (1998 ▶); Chan-Bacab et al. (2009 ▶); Korba, Montero et al. (2008 ▶); Stachulski et al. (2011a ▶ b ▶). For the biological activity of the anti-parasitic agent nitazoxanide {systematic name: [2-[(5-nitro-1,3-thiazol-2-yl)carbamoyl]phenyl]ethanoate}, see: Hemp­hill et al. (2006 ▶); Rossignol et al. (2006 ▶). For the structure of nitazoxanide, see: Bruno et al. (2010 ▶). For the effect of crystallization from different solvents on drug properties, see: Trask et al. (2004 ▶).

Experimental

Crystal data

C10H7N3O4S·C5H5N

M = 344.35

Triclinic,

a = 6.9826 (3) Å

b = 10.0462 (5) Å

c = 11.8387 (7) Å

α = 102.998 (5)°

β = 99.037 (5)°

γ = 104.367 (4)°

V = 763.69 (7) Å3

Z = 2

Cu Kα radiation

μ = 2.16 mm−1

T = 293 K

0.20 × 0.15 × 0.10 mm

Data collection

Agilent Xcalibur Onyx Nova diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011 ▶) T min = 0.712, T max = 0.806

4493 measured reflections

2481 independent reflections

2349 reflections with I > 2σ(I)

R int = 0.016

Refinement

R[F 2 > 2σ(F 2)] = 0.028

wR(F 2) = 0.075

S = 1.08

2481 reflections

265 parameters

All H-atom parameters refined

Δρmax = 0.20 e Å−3

Δρmin = −0.25 e Å−3

Data collection: CrysAlis PRO (Agilent, 2011 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: OLEX2 (Dolomanov et al., 2009 ▶); software used to prepare material for publication: OLEX2.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812016133/qm2062sup1.cif

Supplementary material file. DOI: 10.1107/S1600536812016133/qm2062Isup2.mol

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812016133/qm2062Isup3.hkl

Supplementary material file. DOI: 10.1107/S1600536812016133/qm2062Isup4.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C10H7N3O4S·C5H5N	Z = 2
Mr = 344.35	F(000) = 356
Triclinic, P1	Dx = 1.497 Mg m−3
a = 6.9826 (3) Å	Cu Kα radiation, λ = 1.5418 Å
b = 10.0462 (5) Å	Cell parameters from 3840 reflections
c = 11.8387 (7) Å	θ = 3.9–65.7°
α = 102.998 (5)°	µ = 2.16 mm−1
β = 99.037 (5)°	T = 293 K
γ = 104.367 (4)°	Rod, colorless
V = 763.69 (7) Å3	0.20 × 0.15 × 0.10 mm

Agilent Xcalibur Onyx Nova diffractometer	2481 independent reflections
Radiation source: Nova (Cu) X-ray Source	2349 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.016
Detector resolution: 8.2417 pixels mm-1	θmax = 64.0°, θmin = 3.9°
ω scans	h = −4→8
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	k = −11→11
Tmin = 0.712, Tmax = 0.806	l = −13→13
4493 measured reflections

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)] = 0.028	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.075	All H-atom parameters refined
S = 1.08	w = 1/[σ2(Fo2) + (0.0385P)2 + 0.2467P] where P = (Fo2 + 2Fc2)/3
2481 reflections	(Δ/σ)max = 0.001
265 parameters	Δρmax = 0.20 e Å−3
0 restraints	Δρmin = −0.25 e Å−3

Experimental. Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

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
S1	0.13956 (5)	0.44049 (4)	−0.18461 (3)	0.02193 (13)
O2	0.38793 (16)	0.69194 (12)	−0.07942 (9)	0.0287 (3)
O4	−0.09371 (17)	0.24233 (13)	−0.40776 (9)	0.0379 (3)
O5	−0.23353 (17)	0.06550 (12)	−0.34113 (10)	0.0375 (3)
N6	−0.12170 (18)	0.18630 (14)	−0.32633 (11)	0.0274 (3)
N7	0.31757 (17)	0.56377 (13)	0.04990 (11)	0.0200 (3)
N8	0.59845 (19)	0.69146 (13)	0.49121 (11)	0.0275 (3)
C9	0.5749 (2)	0.80811 (15)	0.24522 (13)	0.0208 (3)
C10	0.5468 (2)	0.80762 (15)	0.12457 (12)	0.0201 (3)
N11	0.09847 (18)	0.33048 (13)	−0.00698 (11)	0.0225 (3)
C12	0.4136 (2)	0.68695 (15)	0.02405 (12)	0.0208 (3)
C13	−0.0197 (2)	0.22865 (17)	−0.10729 (14)	0.0241 (3)
C14	−0.0158 (2)	0.26888 (16)	−0.20893 (13)	0.0230 (3)
C15	0.8152 (2)	1.04417 (17)	0.29859 (14)	0.0290 (4)
C16	0.1899 (2)	0.44557 (15)	−0.03509 (12)	0.0196 (3)
C17	0.7287 (2)	0.61931 (18)	0.51622 (16)	0.0344 (4)
C18	0.5727 (3)	0.7465 (2)	0.69334 (16)	0.0470 (5)
C19	0.6541 (2)	0.92756 (16)	0.09458 (14)	0.0252 (3)
C20	0.7871 (2)	1.04502 (17)	0.17969 (15)	0.0296 (4)
C21	0.5227 (3)	0.75377 (18)	0.57844 (15)	0.0354 (4)
C22	0.7067 (3)	0.6728 (2)	0.71945 (17)	0.0518 (6)
C23	0.7866 (3)	0.6082 (2)	0.6301 (2)	0.0489 (5)
C24	0.7100 (2)	0.92842 (16)	0.33129 (14)	0.0251 (3)
O1	0.47188 (15)	0.69476 (11)	0.27650 (9)	0.0237 (2)
H19	0.631 (3)	0.9235 (18)	0.0134 (17)	0.029 (4)*
H24	0.725 (3)	0.9313 (19)	0.4158 (17)	0.032 (4)*
H20	0.857 (3)	1.127 (2)	0.1564 (17)	0.040 (5)*
H13	−0.093 (3)	0.138 (2)	−0.1026 (15)	0.028 (4)*
H15	0.906 (3)	1.122 (2)	0.3591 (17)	0.035 (5)*
H7	0.332 (3)	0.561 (2)	0.1221 (18)	0.033 (5)*
H17	0.779 (3)	0.575 (2)	0.4501 (18)	0.040 (5)*
H21	0.427 (3)	0.805 (2)	0.5559 (19)	0.052 (6)*
H22	0.739 (4)	0.670 (3)	0.799 (2)	0.075 (7)*
H18	0.514 (4)	0.800 (3)	0.762 (2)	0.068 (7)*
H23	0.877 (3)	0.558 (2)	0.641 (2)	0.056 (6)*
H25	0.525 (4)	0.698 (3)	0.355 (2)	0.073 (8)*

	U11	U22	U33	U12	U13	U23
S1	0.0230 (2)	0.0258 (2)	0.01336 (19)	0.00558 (15)	0.00094 (14)	0.00226 (14)
O2	0.0343 (6)	0.0325 (6)	0.0151 (5)	0.0044 (5)	0.0018 (4)	0.0073 (4)
O4	0.0353 (6)	0.0502 (7)	0.0181 (6)	0.0042 (5)	0.0012 (5)	0.0023 (5)
O5	0.0310 (6)	0.0309 (6)	0.0347 (7)	−0.0005 (5)	−0.0007 (5)	−0.0057 (5)
N6	0.0209 (6)	0.0329 (8)	0.0206 (7)	0.0062 (6)	0.0005 (5)	−0.0030 (6)
N7	0.0223 (6)	0.0237 (6)	0.0121 (6)	0.0062 (5)	0.0014 (5)	0.0033 (5)
N8	0.0310 (7)	0.0258 (7)	0.0186 (6)	−0.0012 (5)	0.0002 (5)	0.0063 (5)
C9	0.0200 (7)	0.0237 (7)	0.0195 (7)	0.0088 (6)	0.0045 (6)	0.0049 (6)
C10	0.0200 (7)	0.0232 (7)	0.0176 (7)	0.0096 (6)	0.0037 (6)	0.0035 (6)
N11	0.0227 (6)	0.0238 (6)	0.0200 (6)	0.0071 (5)	0.0034 (5)	0.0044 (5)
C12	0.0194 (7)	0.0249 (8)	0.0186 (7)	0.0086 (6)	0.0038 (6)	0.0051 (6)
C13	0.0208 (7)	0.0237 (8)	0.0249 (8)	0.0062 (6)	0.0032 (6)	0.0027 (6)
C14	0.0192 (7)	0.0255 (8)	0.0197 (7)	0.0064 (6)	0.0010 (6)	−0.0006 (6)
C15	0.0291 (8)	0.0231 (8)	0.0263 (8)	0.0031 (7)	0.0008 (7)	−0.0009 (7)
C16	0.0186 (7)	0.0247 (7)	0.0158 (7)	0.0097 (6)	0.0031 (5)	0.0030 (6)
C17	0.0292 (8)	0.0318 (9)	0.0379 (10)	0.0005 (7)	0.0043 (7)	0.0128 (8)
C18	0.0652 (13)	0.0402 (10)	0.0225 (9)	−0.0032 (9)	0.0079 (9)	0.0052 (8)
C19	0.0273 (8)	0.0267 (8)	0.0220 (8)	0.0086 (6)	0.0044 (6)	0.0078 (6)
C20	0.0320 (8)	0.0247 (8)	0.0300 (9)	0.0047 (7)	0.0058 (7)	0.0084 (7)
C21	0.0433 (10)	0.0320 (9)	0.0248 (9)	0.0046 (8)	0.0050 (7)	0.0047 (7)
C22	0.0655 (13)	0.0449 (11)	0.0231 (10)	−0.0172 (10)	−0.0096 (9)	0.0168 (9)
C23	0.0374 (10)	0.0422 (11)	0.0595 (14)	−0.0019 (9)	−0.0110 (9)	0.0292 (10)
C24	0.0268 (8)	0.0264 (8)	0.0187 (8)	0.0074 (6)	0.0022 (6)	0.0018 (6)
O1	0.0269 (5)	0.0253 (6)	0.0146 (5)	0.0025 (4)	0.0018 (4)	0.0048 (4)

S1—C14	1.7269 (15)	C13—H13	0.944 (18)
S1—C16	1.7363 (14)	C15—C20	1.393 (2)
O2—C12	1.2240 (18)	C15—C24	1.382 (2)
O4—N6	1.2381 (17)	C15—H15	0.94 (2)
O5—N6	1.2265 (18)	C17—C23	1.383 (3)
N6—C14	1.4217 (19)	C17—H17	0.97 (2)
N7—C12	1.3775 (19)	C18—C21	1.373 (3)
N7—C16	1.3684 (19)	C18—C22	1.369 (3)
N7—H7	0.85 (2)	C18—H18	1.06 (2)
N8—C17	1.334 (2)	C19—C20	1.377 (2)
N8—C21	1.335 (2)	C19—H19	0.939 (18)
C9—C10	1.410 (2)	C20—H20	0.97 (2)
C9—C24	1.403 (2)	C21—H21	0.98 (2)
C9—O1	1.3483 (18)	C22—C23	1.381 (3)
C10—C12	1.481 (2)	C22—H22	0.94 (3)
C10—C19	1.403 (2)	C23—H23	0.92 (2)
N11—C13	1.365 (2)	C24—H24	0.983 (19)
N11—C16	1.3148 (19)	O1—H25	0.93 (3)
C13—C14	1.355 (2)
C14—S1—C16	86.32 (7)	N11—C16—S1	116.83 (11)
O4—N6—C14	116.98 (13)	N11—C16—N7	121.36 (13)
O5—N6—O4	124.16 (13)	N8—C17—C23	121.43 (18)
O5—N6—C14	118.86 (13)	N8—C17—H17	116.3 (11)
C12—N7—H7	119.5 (13)	C23—C17—H17	122.3 (11)
C16—N7—C12	123.00 (12)	C21—C18—H18	121.1 (13)
C16—N7—H7	117.4 (13)	C22—C18—C21	118.52 (19)
C17—N8—C21	118.94 (14)	C22—C18—H18	120.4 (13)
C24—C9—C10	118.84 (13)	C10—C19—H19	116.6 (11)
O1—C9—C10	120.13 (13)	C20—C19—C10	121.77 (14)
O1—C9—C24	121.02 (13)	C20—C19—H19	121.6 (11)
C9—C10—C12	124.80 (13)	C15—C20—H20	121.2 (11)
C19—C10—C9	118.97 (13)	C19—C20—C15	118.89 (15)
C19—C10—C12	116.22 (13)	C19—C20—H20	119.8 (11)
C16—N11—C13	109.77 (12)	N8—C21—C18	122.73 (18)
O2—C12—N7	119.41 (13)	N8—C21—H21	116.0 (13)
O2—C12—C10	123.02 (13)	C18—C21—H21	121.2 (13)
N7—C12—C10	117.56 (12)	C18—C22—C23	119.32 (17)
N11—C13—H13	120.4 (11)	C18—C22—H22	116.7 (16)
C14—C13—N11	114.35 (14)	C23—C22—H22	124.0 (16)
C14—C13—H13	125.2 (11)	C17—C23—H23	116.4 (15)
N6—C14—S1	120.07 (11)	C22—C23—C17	119.06 (19)
C13—C14—S1	112.72 (11)	C22—C23—H23	124.5 (15)
C13—C14—N6	127.21 (14)	C9—C24—H24	119.1 (11)
C20—C15—H15	121.3 (11)	C15—C24—C9	120.72 (14)
C24—C15—C20	120.79 (15)	C15—C24—H24	120.1 (11)
C24—C15—H15	117.9 (11)	C9—O1—H25	111.8 (16)
N7—C16—S1	121.81 (11)

D—H···A	D—H	H···A	D···A	D—H···A
N7—H7···O1	0.85 (2)	1.95 (2)	2.6248 (16)	135.9 (18)
O1—H25···N8	0.94 (2)	1.64 (2)	2.5671 (16)	175 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N7—H7⋯O1	0.85 (2)	1.95 (2)	2.6248 (16)	135.9 (18)
O1—H25⋯N8	0.94 (2)	1.64 (2)	2.5671 (16)	175 (3)