Crystal structure of 2-nitro-N-(5-nitro-1,3-thia-zol-2-yl)benzamide.

In the title compound, C10H6N4O5S, the mean plane of the non-H atoms of the central amide fragment C-N-C(=O)-C [r.m.s. deviation = 0.0294 Å] forms dihedral angles of 12.48 (7) and 46.66 (9)° with the planes of the thia-zole and benzene rings, respectively. In the crystal, mol-ecules are linked by N-H⋯O hydrogen bonds, forming chains along [001]. In addition, weak C-H⋯O hydrogen bonds link these chains, forming a two-dimensional network, containing R (4) 4(28) ring motifs parallel to (100).

Related literature

For related structures, see: Bruno et al. (2010 ▶, 2013 ▶); Liu et al. (2013 ▶). For anti­viral and anti­parasitic properties of thia­zolides, see: Korba et al. (2008 ▶). For hydrogen-bond details, see: n class="Chemical">Nardelli (1995 ▶).

Experimental

Crystal data

C10H6N4O5S

M = 294.25

Monoclinic,

a = 9.6949 (2) Å

b = 12.4192 (2) Å

c = 9.8763 (2) Å

β = 94.948 (1)°

V = 1184.70 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.30 mm−1

T = 295 K

0.20 × 0.17 × 0.12 mm

Data collection

Nonius KappaCCD diffractometer

4714 measured reflections

2424 independent reflections

1867 reflections with I > 2σ(I)

R int = 0.017

Refinement

R[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.136

S = 0.97

2424 reflections

181 parameters

H-atom parameters constrained

Δρmax = 0.51 e Å−3

Δρmin = −0.27 e Å−3

Data collection: COLLECT (Nonius, 2000 ▶); cell refinement: SCALEPACK (Otwinowski & Minor, 1997 ▶); data reduction: DEn class="Chemical">NZO (Otwinowski & Minor, 1997 ▶) and SCALEPACK; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶) and Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: WinGX (Farrugia, 2012 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536814024374/lh5737sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814024374/lh5737Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814024374/lh5737Isup3.cml

Click here for additional data file.

. DOI: 10.1107/S1600536814024374/lh5737fig1.tif

The mol­ecular structure of (I) with displacement ellipsoids drawn at the 50% probability level. H atoms are shown as spheres of arbitrary radius.

Click here for additional data file.

4 4 . DOI: 10.1107/S1600536814024374/lh5737fig2.tif

Part of the crystal structure of (I), showing the formation of R4 4(28) rings within a 2-D hydrogen-bonded network (dashed lines) running parallel to (100) [Symmetry codes: (i) x, −y+1/2, z-1/2; (ii) x, y-1, z].

CCDC reference: 1032923

Additional supporting information: crystallographic information; 3D view; checkCIF report

C10H6N4O5S	F(000) = 600
Mr = 294.25	Dx = 1.650 Mg m−3
Monoclinic, P21/c	Melting point: 515(1) K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 9.6949 (2) Å	Cell parameters from 2543 reflections
b = 12.4192 (2) Å	θ = 2.9–26.4°
c = 9.8763 (2) Å	µ = 0.30 mm−1
β = 94.948 (1)°	T = 295 K
V = 1184.70 (4) Å3	Block, brown
Z = 4	0.20 × 0.17 × 0.12 mm

Nonius KappaCCD diffractometer	1867 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.017
Graphite monochromator	θmax = 26.4°, θmin = 3.3°
CCD rotation images, thick slices scans	h = −12→12
4714 measured reflections	k = −15→15
2424 independent reflections	l = −12→12

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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.136	H-atom parameters constrained
S = 0.97	w = 1/[σ2(Fo2) + (0.0901P)2 + 0.3259P] where P = (Fo2 + 2Fc2)/3
2424 reflections	(Δ/σ)max < 0.001
181 parameters	Δρmax = 0.51 e Å−3
0 restraints	Δρmin = −0.27 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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	0.33684 (6)	0.47701 (4)	0.20035 (5)	0.0441 (2)
O3	0.22493 (17)	0.28583 (12)	0.26475 (14)	0.0502 (4)
N1	0.4288 (2)	0.68288 (15)	0.16636 (19)	0.0473 (4)
N2	0.3021 (2)	0.46806 (14)	−0.06343 (17)	0.0463 (5)
N3	0.24829 (18)	0.30650 (13)	0.04092 (17)	0.0420 (4)
H3	0.2390	0.2766	−0.0379	0.050*
O2	0.4626 (2)	0.75643 (14)	0.09317 (19)	0.0648 (5)
C6	0.0858 (2)	0.07681 (18)	0.1823 (2)	0.0449 (5)
C5	0.1907 (2)	0.13054 (16)	0.12231 (19)	0.0400 (5)
C10	0.2795 (2)	0.06972 (18)	0.0508 (2)	0.0470 (5)
H10	0.3508	0.1032	0.0096	0.056*
C1	0.3749 (2)	0.58660 (17)	0.1039 (2)	0.0421 (5)
C3	0.2907 (2)	0.41287 (16)	0.04889 (19)	0.0395 (5)
C4	0.2206 (2)	0.24675 (16)	0.1504 (2)	0.0401 (5)
O1	0.4402 (2)	0.68685 (15)	0.29129 (17)	0.0706 (5)
C8	0.1593 (3)	−0.09204 (19)	0.1018 (2)	0.0576 (6)
H8	0.1498	−0.1664	0.0950	0.069*
N4	−0.0150 (2)	0.1388 (2)	0.2531 (3)	0.0650 (6)
C2	0.3492 (2)	0.56887 (17)	−0.0307 (2)	0.0458 (5)
H2	0.3624	0.6212	−0.0957	0.055*
C9	0.2627 (3)	−0.04074 (18)	0.0405 (2)	0.0536 (6)
H9	0.3224	−0.0807	−0.0086	0.064*
O5	−0.0429 (3)	0.1061 (2)	0.3650 (3)	0.1011 (8)
C7	0.0691 (3)	−0.03301 (19)	0.1736 (2)	0.0545 (6)
H7	−0.0015	−0.0670	0.2153	0.065*
O4	−0.0647 (2)	0.2185 (2)	0.1957 (3)	0.0905 (7)

	U11	U22	U33	U12	U13	U23
S1	0.0603 (4)	0.0397 (3)	0.0326 (3)	−0.0048 (2)	0.0058 (2)	−0.0005 (2)
O3	0.0742 (11)	0.0441 (8)	0.0327 (8)	−0.0080 (7)	0.0074 (7)	−0.0032 (6)
N1	0.0534 (11)	0.0408 (10)	0.0477 (11)	−0.0016 (8)	0.0051 (8)	0.0001 (8)
N2	0.0615 (11)	0.0440 (10)	0.0331 (9)	−0.0017 (8)	0.0025 (8)	0.0043 (7)
N3	0.0559 (11)	0.0386 (9)	0.0318 (9)	−0.0032 (8)	0.0054 (7)	−0.0030 (7)
O2	0.0838 (13)	0.0436 (9)	0.0664 (11)	−0.0114 (8)	0.0033 (9)	0.0092 (8)
C6	0.0490 (12)	0.0471 (12)	0.0388 (11)	−0.0053 (10)	0.0044 (9)	−0.0067 (9)
C5	0.0490 (12)	0.0394 (11)	0.0313 (10)	−0.0029 (9)	0.0019 (8)	−0.0002 (8)
C10	0.0580 (13)	0.0458 (12)	0.0382 (11)	0.0012 (10)	0.0100 (10)	0.0018 (9)
C1	0.0463 (12)	0.0400 (11)	0.0403 (11)	−0.0003 (9)	0.0060 (9)	0.0015 (8)
C3	0.0453 (11)	0.0400 (11)	0.0337 (10)	0.0002 (9)	0.0061 (8)	0.0009 (8)
C4	0.0447 (11)	0.0405 (11)	0.0349 (10)	−0.0008 (9)	0.0029 (8)	−0.0020 (8)
O1	0.1054 (15)	0.0597 (11)	0.0466 (10)	−0.0183 (10)	0.0060 (9)	−0.0093 (8)
C8	0.0830 (18)	0.0375 (12)	0.0515 (14)	−0.0025 (12)	0.0019 (13)	0.0042 (10)
N4	0.0504 (12)	0.0725 (16)	0.0738 (15)	−0.0156 (11)	0.0157 (11)	−0.0284 (12)
C2	0.0539 (13)	0.0413 (12)	0.0426 (12)	−0.0009 (10)	0.0074 (10)	0.0081 (9)
C9	0.0742 (16)	0.0411 (12)	0.0464 (13)	0.0118 (11)	0.0107 (11)	0.0009 (10)
O5	0.0955 (17)	0.130 (2)	0.0857 (16)	−0.0291 (15)	0.0539 (14)	−0.0220 (14)
C7	0.0674 (15)	0.0508 (14)	0.0458 (13)	−0.0162 (11)	0.0072 (11)	0.0017 (10)
O4	0.0802 (15)	0.0786 (15)	0.1127 (18)	0.0220 (12)	0.0079 (13)	−0.0326 (14)

S1—C3	1.720 (2)	C5—C10	1.384 (3)
S1—C1	1.720 (2)	C5—C4	1.493 (3)
O3—C4	1.227 (2)	C10—C9	1.384 (3)
N1—O2	1.227 (2)	C10—H10	0.9300
N1—O1	1.230 (2)	C1—C2	1.349 (3)
N1—C1	1.424 (3)	C8—C9	1.372 (4)
N2—C3	1.317 (2)	C8—C7	1.383 (4)
N2—C2	1.362 (3)	C8—H8	0.9300
N3—C4	1.357 (3)	N4—O4	1.218 (4)
N3—C3	1.384 (3)	N4—O5	1.230 (3)
N3—H3	0.8600	C2—H2	0.9300
C6—C7	1.375 (3)	C9—H9	0.9300
C6—C5	1.391 (3)	C7—H7	0.9300
C6—N4	1.468 (3)
C3—S1—C1	86.39 (10)	N2—C3—S1	117.22 (16)
O2—N1—O1	123.74 (19)	N3—C3—S1	123.06 (15)
O2—N1—C1	118.47 (18)	O3—C4—N3	121.59 (19)
O1—N1—C1	117.78 (18)	O3—C4—C5	122.95 (18)
C3—N2—C2	109.22 (17)	N3—C4—C5	115.42 (17)
C4—N3—C3	123.71 (17)	C9—C8—C7	119.9 (2)
C4—N3—H3	118.1	C9—C8—H8	120.0
C3—N3—H3	118.1	C7—C8—H8	120.0
C7—C6—C5	122.4 (2)	O4—N4—O5	125.2 (3)
C7—C6—N4	118.1 (2)	O4—N4—C6	117.3 (2)
C5—C6—N4	119.5 (2)	O5—N4—C6	117.5 (3)
C10—C5—C6	117.7 (2)	C1—C2—N2	114.44 (18)
C10—C5—C4	120.18 (19)	C1—C2—H2	122.8
C6—C5—C4	121.46 (18)	N2—C2—H2	122.8
C5—C10—C9	120.3 (2)	C8—C9—C10	120.9 (2)
C5—C10—H10	119.9	C8—C9—H9	119.6
C9—C10—H10	119.9	C10—C9—H9	119.6
C2—C1—N1	126.41 (19)	C6—C7—C8	118.8 (2)
C2—C1—S1	112.72 (16)	C6—C7—H7	120.6
N1—C1—S1	120.87 (16)	C8—C7—H7	120.6
N2—C3—N3	119.67 (18)
C7—C6—C5—C10	0.5 (3)	C3—N3—C4—O3	3.8 (3)
N4—C6—C5—C10	−176.9 (2)	C3—N3—C4—C5	−173.84 (18)
C7—C6—C5—C4	−170.5 (2)	C10—C5—C4—O3	−127.2 (2)
N4—C6—C5—C4	12.1 (3)	C6—C5—C4—O3	43.6 (3)
C6—C5—C10—C9	0.1 (3)	C10—C5—C4—N3	50.3 (3)
C4—C5—C10—C9	171.2 (2)	C6—C5—C4—N3	−138.8 (2)
O2—N1—C1—C2	−4.0 (3)	C7—C6—N4—O4	−131.6 (3)
O1—N1—C1—C2	176.9 (2)	C5—C6—N4—O4	45.9 (3)
O2—N1—C1—S1	175.42 (16)	C7—C6—N4—O5	48.1 (3)
O1—N1—C1—S1	−3.7 (3)	C5—C6—N4—O5	−134.4 (2)
C3—S1—C1—C2	1.01 (17)	N1—C1—C2—N2	177.9 (2)
C3—S1—C1—N1	−178.52 (19)	S1—C1—C2—N2	−1.6 (3)
C2—N2—C3—N3	−178.09 (18)	C3—N2—C2—C1	1.4 (3)
C2—N2—C3—S1	−0.6 (3)	C7—C8—C9—C10	0.8 (4)
C4—N3—C3—N2	−173.3 (2)	C5—C10—C9—C8	−0.7 (3)
C4—N3—C3—S1	9.4 (3)	C5—C6—C7—C8	−0.5 (3)
C1—S1—C3—N2	−0.22 (18)	N4—C6—C7—C8	177.0 (2)
C1—S1—C3—N3	177.18 (19)	C9—C8—C7—C6	−0.2 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3···O3i	0.86	2.09	2.949 (2)	175
C9—H9···O2ii	0.93	2.59	3.193 (3)	123

Table 1

Hydrogen-bond geometry (, )

DHA	DH	HA	D A	DHA
N3H3O3i	0.86	2.09	2.949(2)	175
C9H9O2ii	0.93	2.59	3.193(3)	123

Symmetry codes: (i) ; (ii) .