3,5-Dinitro-N-(1,3-thia-zol-2-yl)benzamide monohydrate.

In the title compound, C(10)H(6)N(4)O(5)S·H(2)O, the thia-zole ring is twisted at a dihedral angle of 25.87 (7)° with respect to the benzene ring. The water mol-ecule is linked with the benzamide mol-ecules via N-H⋯O, O-H⋯N and O-H⋯O hydrogen bonds. In the crystal, π-π stacking is observed between nearly parallel [dihedral angle = 7.02 (7)°] thia-zole and benzene rings of adjacent mol-ecules, the centroid-centroid distances being 3.7107 (9) and 3.7158 (9) Å, respectively.

Related literature

For the effect of substituents on the structures of benzanilides, see: Gowda et al. (2008 ▶).

Experimental

Crystal data

C10H6N4O5S·H2O

M = 312.26

Monoclinic,

a = 13.7075 (12) Å

b = 6.9734 (6) Å

c = 13.8507 (13) Å

β = 108.512 (1)°

V = 1255.45 (19) Å3

Z = 4

Mo Kα radiation

μ = 0.30 mm−1

T = 296 K

0.28 × 0.07 × 0.06 mm

Data collection

Bruker SMART 1000 CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ▶) T min = 0.922, T max = 0.983

6750 measured reflections

2214 independent reflections

1937 reflections with I > 2σ(I)

R int = 0.015

Refinement

R[F 2 > 2σ(F 2)] = 0.029

wR(F 2) = 0.088

S = 1.02

2214 reflections

203 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.19 e Å−3

Δρmin = −0.21 e Å−3

Data collection: SMART (Bruker, 1998 ▶); cell refinement: SAINT (Bruker, 2006 ▶); data reduction: SAINT and CrystalStructure (Rigaku/MSC, 2006 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEPII (Johnson, 1976 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811005228/xu5155sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811005228/xu5155Isup2.hkl

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

C10H6N4O5S·H2O	F(000) = 640
Mr = 312.26	Dx = 1.652 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 9023 reflections
a = 13.7075 (12) Å	θ = 1.8–25.0°
b = 6.9734 (6) Å	µ = 0.30 mm−1
c = 13.8507 (13) Å	T = 296 K
β = 108.512 (1)°	Needle, colourless
V = 1255.45 (19) Å3	0.28 × 0.07 × 0.06 mm
Z = 4

Bruker SMART 1000 CCD diffractometer	2214 independent reflections
Radiation source: fine-focus sealed tube	1937 reflections with I > 2σ(I)
graphite	Rint = 0.015
ω scans	θmax = 25.0°, θmin = 3.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	h = −16→15
Tmin = 0.922, Tmax = 0.983	k = −8→8
6750 measured reflections	l = −16→16

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.029	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.088	w = 1/[σ2(Fo2) + (0.0569P)2 + 0.2612P] where P = (Fo2 + 2Fc2)/3
S = 1.02	(Δ/σ)max = 0.001
2214 reflections	Δρmax = 0.19 e Å−3
203 parameters	Δρmin = −0.21 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0069 (14)

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	−0.17423 (3)	0.90512 (6)	0.12088 (3)	0.03884 (16)
O1	0.02312 (8)	0.95294 (19)	0.11971 (8)	0.0469 (3)
O2	0.35736 (11)	1.1250 (3)	0.08520 (11)	0.0793 (5)
O3	0.49514 (9)	1.0180 (3)	0.19517 (10)	0.0669 (4)
O4	0.48076 (9)	0.7824 (2)	0.51780 (10)	0.0590 (4)
O5	0.34262 (11)	0.8314 (3)	0.55577 (10)	0.0777 (5)
N1	−0.14748 (10)	0.9651 (2)	0.31080 (10)	0.0403 (3)
N2	0.00921 (9)	0.94048 (19)	0.27755 (10)	0.0351 (3)
H2N	0.0335 (15)	0.929 (3)	0.3435 (15)	0.046 (5)*
N3	0.40286 (11)	1.0453 (2)	0.16479 (11)	0.0505 (4)
N4	0.39071 (10)	0.8282 (2)	0.49550 (10)	0.0453 (4)
C1	−0.28028 (12)	0.9200 (2)	0.16129 (13)	0.0425 (4)
H1	−0.3480	0.9069	0.1193	0.051*
C2	−0.25176 (12)	0.9531 (2)	0.26157 (13)	0.0429 (4)
H2	−0.2996	0.9672	0.2960	0.052*
C3	−0.09807 (11)	0.9410 (2)	0.24567 (11)	0.0331 (3)
C4	0.06477 (11)	0.9452 (2)	0.21168 (11)	0.0338 (3)
C5	0.17976 (11)	0.9424 (2)	0.25696 (11)	0.0324 (3)
C6	0.23598 (11)	0.9885 (2)	0.19236 (12)	0.0368 (4)
H6	0.2027	1.0230	0.1251	0.044*
C7	0.34216 (11)	0.9820 (2)	0.23006 (12)	0.0379 (4)
C8	0.39520 (12)	0.9255 (2)	0.32777 (12)	0.0382 (4)
H8	0.4665	0.9150	0.3507	0.046*
C9	0.33678 (11)	0.8856 (2)	0.38975 (11)	0.0352 (3)
C10	0.23081 (11)	0.8948 (2)	0.35798 (11)	0.0340 (3)
H10	0.1944	0.8698	0.4029	0.041*
O6	0.07962 (11)	0.8457 (2)	0.48713 (10)	0.0503 (3)
H6B	0.0571 (18)	0.752 (4)	0.4970 (18)	0.076 (9)*
H6C	0.0932 (18)	0.912 (3)	0.5399 (19)	0.073 (8)*

	U11	U22	U33	U12	U13	U23
S1	0.0299 (2)	0.0482 (3)	0.0354 (2)	−0.00058 (15)	0.00610 (16)	0.00073 (16)
O1	0.0341 (6)	0.0737 (9)	0.0322 (6)	0.0033 (5)	0.0092 (5)	0.0028 (5)
O2	0.0531 (8)	0.1362 (15)	0.0526 (8)	−0.0101 (8)	0.0222 (7)	0.0276 (9)
O3	0.0322 (7)	0.1079 (12)	0.0660 (9)	−0.0099 (7)	0.0233 (6)	−0.0043 (8)
O4	0.0356 (6)	0.0801 (10)	0.0533 (7)	0.0133 (6)	0.0030 (5)	0.0077 (7)
O5	0.0573 (9)	0.1376 (15)	0.0406 (7)	0.0245 (9)	0.0190 (6)	0.0190 (8)
N1	0.0314 (7)	0.0498 (8)	0.0414 (7)	0.0005 (6)	0.0139 (6)	0.0001 (6)
N2	0.0260 (7)	0.0474 (8)	0.0312 (7)	−0.0003 (5)	0.0078 (5)	−0.0010 (6)
N3	0.0379 (8)	0.0734 (11)	0.0447 (8)	−0.0118 (7)	0.0197 (7)	−0.0075 (7)
N4	0.0388 (8)	0.0546 (9)	0.0393 (7)	0.0046 (6)	0.0076 (6)	0.0011 (6)
C1	0.0275 (8)	0.0450 (9)	0.0529 (10)	−0.0009 (6)	0.0096 (7)	0.0055 (7)
C2	0.0289 (8)	0.0485 (10)	0.0540 (10)	0.0014 (6)	0.0170 (7)	0.0057 (8)
C3	0.0285 (7)	0.0355 (8)	0.0349 (8)	0.0006 (6)	0.0097 (6)	0.0016 (6)
C4	0.0299 (8)	0.0377 (8)	0.0340 (8)	0.0001 (6)	0.0107 (6)	−0.0008 (6)
C5	0.0280 (8)	0.0339 (8)	0.0355 (8)	−0.0005 (5)	0.0106 (6)	−0.0036 (6)
C6	0.0329 (8)	0.0437 (9)	0.0339 (8)	−0.0024 (6)	0.0107 (6)	−0.0032 (7)
C7	0.0329 (8)	0.0449 (9)	0.0398 (8)	−0.0054 (6)	0.0169 (7)	−0.0069 (7)
C8	0.0281 (7)	0.0435 (9)	0.0424 (9)	−0.0005 (6)	0.0105 (6)	−0.0091 (7)
C9	0.0322 (8)	0.0377 (8)	0.0341 (8)	0.0024 (6)	0.0082 (6)	−0.0037 (6)
C10	0.0330 (8)	0.0358 (8)	0.0352 (8)	0.0008 (6)	0.0137 (6)	−0.0021 (6)
O6	0.0545 (8)	0.0628 (9)	0.0371 (7)	−0.0040 (7)	0.0195 (6)	−0.0006 (6)

S1—C1	1.7187 (16)	C1—H1	0.9300
S1—C3	1.7304 (15)	C2—H2	0.9300
O1—C4	1.2205 (18)	C4—C5	1.500 (2)
O2—N3	1.215 (2)	C5—C10	1.391 (2)
O3—N3	1.2147 (18)	C5—C6	1.391 (2)
O4—N4	1.2162 (17)	C6—C7	1.382 (2)
O5—N4	1.2171 (18)	C6—H6	0.9300
N1—C3	1.299 (2)	C7—C8	1.375 (2)
N1—C2	1.377 (2)	C8—C9	1.376 (2)
N2—C4	1.3618 (19)	C8—H8	0.9300
N2—C3	1.3947 (19)	C9—C10	1.379 (2)
N2—H2N	0.871 (19)	C10—H10	0.9300
N3—C7	1.477 (2)	O6—H6B	0.75 (3)
N4—C9	1.471 (2)	O6—H6C	0.84 (3)
C1—C2	1.338 (2)
C1—S1—C3	88.30 (8)	O1—C4—C5	121.21 (13)
C3—N1—C2	109.65 (14)	N2—C4—C5	117.15 (13)
C4—N2—C3	123.06 (13)	C10—C5—C6	119.83 (13)
C4—N2—H2N	126.6 (12)	C10—C5—C4	123.35 (13)
C3—N2—H2N	110.2 (12)	C6—C5—C4	116.81 (13)
O3—N3—O2	124.34 (15)	C7—C6—C5	118.77 (14)
O3—N3—C7	117.90 (15)	C7—C6—H6	120.6
O2—N3—C7	117.74 (14)	C5—C6—H6	120.6
O4—N4—O5	123.90 (14)	C8—C7—C6	123.06 (14)
O4—N4—C9	118.23 (13)	C8—C7—N3	117.61 (14)
O5—N4—C9	117.87 (13)	C6—C7—N3	119.28 (14)
C2—C1—S1	110.49 (12)	C7—C8—C9	116.21 (14)
C2—C1—H1	124.8	C7—C8—H8	121.9
S1—C1—H1	124.8	C9—C8—H8	121.9
C1—C2—N1	116.08 (14)	C8—C9—C10	123.66 (14)
C1—C2—H2	122.0	C8—C9—N4	117.92 (14)
N1—C2—H2	122.0	C10—C9—N4	118.41 (13)
N1—C3—N2	120.67 (14)	C9—C10—C5	118.33 (13)
N1—C3—S1	115.47 (11)	C9—C10—H10	120.8
N2—C3—S1	123.84 (11)	C5—C10—H10	120.8
O1—C4—N2	121.63 (13)	H6B—O6—H6C	108 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2N···O6	0.871 (19)	1.974 (19)	2.8313 (18)	167.9 (17)
O6—H6B···O1i	0.75 (3)	2.38 (2)	3.0350 (19)	147 (2)
O6—H6C···N1ii	0.84 (3)	2.14 (3)	2.964 (2)	168 (2)

I	J	CgI···CgJ	Dihedral angle	CgI_Perp	CgJ_Perp
1	2i	3.7158 (9)	7.02 (7)	3.3718 (6)	-3.4374 (6)
1	2ii	3.7107 (9)	7.02 (7)	-3.3175 (6)	3.4409 (6)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2N⋯O6	0.871 (19)	1.974 (19)	2.8313 (18)	167.9 (17)
O6—H6B⋯O1i	0.75 (3)	2.38 (2)	3.0350 (19)	147 (2)
O6—H6C⋯N1ii	0.84 (3)	2.14 (3)	2.964 (2)	168 (2)

Symmetry codes: (i) ; (ii) .