N-(2-Nitro-phen-yl)thio-phene-2-carbox-amide.

The title compound, C11H8N2O3S, shows two mol-ecules per asymmetric unit, with the dihedral angles between the benzene and thio-phene rings of 13.53 (6) and 8.50 (5)° being a notable difference between them. An intra-molecular N-H⋯O hydrogen-bond in each mol-ecule generates an S(6) ring motif. The crystal packing shows no classical hydrogen bonds with the mol-ecules being packed to form weak C-H⋯O and C-H⋯S inter-actions leading to R 2 (2)(9) and R 4 (4)(25) rings which are edge-shared, giving layers parallel to (010).

Related literature

For the anti­bacterial and anti­fungal activity of amide compounds, see: Aytemir et al. (2003 ▶); Hrelia et al. (1995 ▶). For a similar compound, see: Moreno-Fuquen et al. (2013 ▶). For hydrogen-bonding information, see: Nardelli (1995 ▶). For hydrogen-bond motifs, see: Etter et al. (1990 ▶).

Experimental

Crystal data

C11H8N2O3S

M = 248.25

Monoclinic,

a = 11.6359 (3) Å

b = 13.2501 (3) Å

c = 17.7412 (4) Å

β = 129.898 (1)°

V = 2098.47 (9) Å3

Z = 8

Mo Kα radiation

μ = 0.31 mm−1

T = 123 K

0.28 × 0.15 × 0.05 mm

Data collection

Oxford Diffraction Xcalibur E diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010 ▶) T min = 0.953, T max = 1.000

10418 measured reflections

5093 independent reflections

4012 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.116

S = 1.04

5093 reflections

315 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.49 e Å−3

Δρmin = −0.43 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2010 ▶); 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: 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/S160053681400912X/tk5309sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681400912X/tk5309Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S160053681400912X/tk5309Isup3.cml

CCDC reference: 998902

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

C11H8N2O3S	F(000) = 1024
Mr = 248.25	Dx = 1.572 Mg m−3
Monoclinic, P21/c	Melting point: 397(1) K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 11.6359 (3) Å	Cell parameters from 4181 reflections
b = 13.2501 (3) Å	θ = 3.4–29.4°
c = 17.7412 (4) Å	µ = 0.31 mm−1
β = 129.898 (1)°	T = 123 K
V = 2098.47 (9) Å3	Tablet, yellow
Z = 8	0.28 × 0.15 × 0.05 mm

Oxford Diffraction Xcalibur E diffractometer	5093 independent reflections
Radiation source: fine-focus sealed tube	4012 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.028
ω scans	θmax = 29.4°, θmin = 3.4°
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)	h = −15→14
Tmin = 0.953, Tmax = 1.000	k = −15→17
10418 measured reflections	l = −22→24

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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.116	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ2(Fo2) + (0.042P)2 + 1.7613P] where P = (Fo2 + 2Fc2)/3
5093 reflections	(Δ/σ)max < 0.001
315 parameters	Δρmax = 0.49 e Å−3
0 restraints	Δρmin = −0.43 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	0.60696 (6)	0.81889 (4)	−0.07981 (4)	0.02441 (14)
S2	0.98321 (6)	0.64159 (5)	0.30229 (4)	0.03015 (16)
O1	0.38729 (16)	0.85064 (13)	−0.05031 (11)	0.0255 (4)
O2	0.77371 (16)	0.93931 (13)	0.29784 (11)	0.0262 (4)
O3	0.73314 (17)	0.91094 (13)	0.39862 (11)	0.0274 (4)
O4	0.70355 (17)	0.70186 (12)	0.26329 (11)	0.0269 (4)
O5	0.38579 (16)	0.59679 (13)	−0.08094 (11)	0.0268 (4)
O6	0.15254 (17)	0.63885 (14)	−0.18258 (11)	0.0303 (4)
N1	0.5542 (2)	0.90436 (14)	0.10981 (13)	0.0184 (4)
N2	0.68724 (19)	0.92377 (13)	0.31503 (12)	0.0193 (4)
N3	0.54164 (19)	0.64179 (14)	0.10488 (13)	0.0189 (4)
N4	0.26905 (19)	0.62585 (14)	−0.09860 (13)	0.0217 (4)
C1	0.7915 (3)	0.82021 (17)	−0.02508 (16)	0.0247 (5)
H1	0.8288	0.8029	−0.0578	0.030*
C2	0.8804 (2)	0.84884 (17)	0.07096 (16)	0.0220 (4)
H2	0.9864	0.8533	0.1126	0.026*
C3	0.7965 (2)	0.87137 (16)	0.10222 (15)	0.0182 (4)
H3	0.8395	0.8922	0.1667	0.022*
C4	0.6440 (2)	0.85876 (15)	0.02591 (14)	0.0171 (4)
C5	0.5153 (2)	0.87066 (16)	0.02341 (14)	0.0180 (4)
C6	0.4632 (2)	0.91537 (15)	0.13495 (14)	0.0171 (4)
C7	0.5258 (2)	0.92336 (15)	0.23390 (15)	0.0173 (4)
C8	0.4367 (2)	0.93183 (16)	0.26042 (16)	0.0218 (4)
H8	0.4816	0.9355	0.3278	0.026*
C9	0.2828 (2)	0.93496 (17)	0.18862 (17)	0.0240 (5)
H9	0.2211	0.9416	0.2060	0.029*
C10	0.2195 (2)	0.92823 (17)	0.09095 (16)	0.0230 (5)
H10	0.1136	0.9307	0.0414	0.028*
C11	0.3066 (2)	0.91801 (16)	0.06396 (15)	0.0200 (4)
H11	0.2599	0.9127	−0.0036	0.024*
C12	1.0568 (2)	0.60694 (18)	0.24879 (17)	0.0268 (5)
H12	1.1610	0.5988	0.2838	0.032*
C13	0.9500 (2)	0.59212 (17)	0.15022 (16)	0.0230 (5)
H13	0.9720	0.5724	0.1092	0.028*
C14	0.8015 (2)	0.60940 (16)	0.11495 (15)	0.0185 (4)
H14	0.7132	0.6030	0.0483	0.022*
C15	0.8039 (2)	0.63702 (16)	0.19220 (14)	0.0188 (4)
C16	0.6807 (2)	0.66372 (16)	0.19215 (15)	0.0194 (4)
C17	0.4018 (2)	0.65097 (15)	0.08063 (14)	0.0172 (4)
C18	0.2688 (2)	0.64194 (16)	−0.01743 (15)	0.0182 (4)
C19	0.1290 (2)	0.64708 (17)	−0.04208 (16)	0.0232 (5)
H19	0.0408	0.6408	−0.1088	0.028*
C20	0.1180 (3)	0.66121 (17)	0.03006 (18)	0.0256 (5)
H20	0.0227	0.6636	0.0137	0.031*
C21	0.2479 (3)	0.67189 (17)	0.12687 (17)	0.0240 (5)
H21	0.2409	0.6827	0.1767	0.029*
C22	0.3873 (2)	0.66709 (16)	0.15197 (16)	0.0212 (4)
H22	0.4747	0.6749	0.2187	0.025*
H3N	0.536 (3)	0.6175 (18)	0.0592 (18)	0.020 (6)*
H1N	0.642 (3)	0.914 (2)	0.156 (2)	0.033 (7)*

	U11	U22	U33	U12	U13	U23
S1	0.0264 (3)	0.0289 (3)	0.0169 (2)	0.0012 (2)	0.0134 (2)	−0.0021 (2)
S2	0.0209 (3)	0.0372 (4)	0.0198 (3)	−0.0010 (2)	0.0073 (2)	−0.0030 (2)
O1	0.0176 (7)	0.0359 (9)	0.0171 (7)	−0.0009 (7)	0.0085 (6)	−0.0018 (6)
O2	0.0178 (7)	0.0417 (10)	0.0203 (7)	−0.0054 (7)	0.0129 (6)	−0.0059 (7)
O3	0.0270 (8)	0.0359 (9)	0.0166 (7)	−0.0021 (7)	0.0128 (7)	0.0020 (7)
O4	0.0264 (8)	0.0321 (9)	0.0173 (7)	0.0015 (7)	0.0118 (6)	−0.0039 (7)
O5	0.0185 (7)	0.0425 (10)	0.0209 (7)	−0.0019 (7)	0.0134 (6)	−0.0061 (7)
O6	0.0232 (8)	0.0442 (10)	0.0150 (7)	0.0044 (7)	0.0084 (6)	0.0006 (7)
N1	0.0128 (8)	0.0254 (10)	0.0147 (8)	−0.0009 (7)	0.0077 (7)	−0.0020 (7)
N2	0.0199 (8)	0.0193 (9)	0.0179 (8)	−0.0012 (7)	0.0117 (7)	−0.0020 (7)
N3	0.0182 (8)	0.0236 (9)	0.0138 (8)	−0.0002 (7)	0.0098 (7)	−0.0025 (7)
N4	0.0191 (9)	0.0257 (10)	0.0179 (8)	−0.0016 (8)	0.0109 (7)	−0.0025 (7)
C1	0.0308 (12)	0.0253 (11)	0.0261 (11)	0.0032 (10)	0.0220 (10)	0.0014 (9)
C2	0.0204 (10)	0.0241 (11)	0.0230 (10)	−0.0010 (9)	0.0147 (9)	0.0006 (9)
C3	0.0210 (10)	0.0174 (10)	0.0203 (10)	−0.0003 (8)	0.0150 (9)	0.0010 (8)
C4	0.0213 (10)	0.0165 (10)	0.0148 (9)	0.0010 (8)	0.0122 (8)	0.0008 (7)
C5	0.0205 (10)	0.0170 (10)	0.0159 (9)	0.0011 (8)	0.0114 (8)	0.0024 (8)
C6	0.0191 (10)	0.0150 (10)	0.0183 (9)	0.0004 (8)	0.0125 (8)	0.0012 (8)
C7	0.0166 (9)	0.0154 (10)	0.0191 (9)	−0.0010 (8)	0.0112 (8)	−0.0005 (8)
C8	0.0268 (11)	0.0205 (11)	0.0243 (10)	−0.0044 (9)	0.0191 (9)	−0.0035 (8)
C9	0.0243 (11)	0.0228 (11)	0.0336 (12)	−0.0039 (9)	0.0225 (10)	−0.0041 (9)
C10	0.0167 (10)	0.0220 (11)	0.0268 (11)	−0.0008 (9)	0.0124 (9)	0.0003 (9)
C11	0.0178 (10)	0.0200 (10)	0.0192 (10)	0.0012 (8)	0.0106 (8)	0.0026 (8)
C12	0.0165 (10)	0.0279 (12)	0.0274 (11)	−0.0012 (9)	0.0102 (9)	0.0028 (9)
C13	0.0225 (10)	0.0215 (11)	0.0275 (11)	−0.0006 (9)	0.0172 (9)	0.0016 (9)
C14	0.0160 (9)	0.0175 (10)	0.0232 (10)	0.0005 (8)	0.0131 (8)	0.0041 (8)
C15	0.0168 (9)	0.0171 (10)	0.0157 (9)	−0.0015 (8)	0.0073 (8)	0.0006 (8)
C16	0.0213 (10)	0.0162 (10)	0.0156 (9)	0.0012 (8)	0.0095 (8)	0.0033 (8)
C17	0.0186 (10)	0.0158 (10)	0.0174 (9)	0.0009 (8)	0.0117 (8)	0.0015 (8)
C18	0.0214 (10)	0.0172 (10)	0.0175 (9)	0.0006 (8)	0.0132 (8)	0.0008 (8)
C19	0.0203 (10)	0.0234 (11)	0.0233 (10)	0.0007 (9)	0.0128 (9)	0.0026 (9)
C20	0.0254 (11)	0.0236 (11)	0.0375 (13)	0.0031 (9)	0.0246 (10)	0.0047 (10)
C21	0.0334 (12)	0.0210 (11)	0.0293 (11)	0.0036 (9)	0.0255 (10)	0.0033 (9)
C22	0.0265 (11)	0.0202 (11)	0.0193 (10)	0.0021 (9)	0.0158 (9)	0.0022 (8)

S1—C1	1.697 (2)	C6—C11	1.401 (3)
S1—C4	1.716 (2)	C6—C7	1.408 (3)
S2—C12	1.699 (3)	C7—C8	1.391 (3)
S2—C15	1.716 (2)	C8—C9	1.380 (3)
O1—C5	1.225 (2)	C8—H8	0.9500
O2—N2	1.242 (2)	C9—C10	1.384 (3)
O3—N2	1.224 (2)	C9—H9	0.9500
O4—C16	1.220 (3)	C10—C11	1.376 (3)
O5—N4	1.243 (2)	C10—H10	0.9500
O6—N4	1.223 (2)	C11—H11	0.9500
N1—C5	1.366 (3)	C12—C13	1.361 (3)
N1—C6	1.395 (3)	C12—H12	0.9500
N1—H1N	0.81 (3)	C13—C14	1.430 (3)
N2—O2	1.242 (2)	C13—H13	0.9500
N2—C7	1.460 (3)	C14—C15	1.401 (3)
N3—C16	1.373 (3)	C14—H14	0.9500
N3—C17	1.396 (3)	C15—C16	1.476 (3)
N3—H3N	0.84 (2)	C17—C22	1.396 (3)
N4—O5	1.243 (2)	C17—C18	1.408 (3)
N4—C18	1.457 (3)	C18—C19	1.390 (3)
C1—C2	1.362 (3)	C19—C20	1.378 (3)
C1—H1	0.9500	C19—H19	0.9500
C2—C3	1.429 (3)	C20—C21	1.387 (3)
C2—H2	0.9500	C20—H20	0.9500
C3—C4	1.388 (3)	C21—C22	1.381 (3)
C3—H3	0.9500	C21—H21	0.9500
C4—C5	1.478 (3)	C22—H22	0.9500
C1—S1—C4	91.88 (10)	C8—C9—C10	119.2 (2)
C12—S2—C15	92.00 (11)	C8—C9—H9	120.4
C5—N1—C6	128.35 (18)	C10—C9—H9	120.4
C5—N1—H1N	118.8 (19)	C11—C10—C9	121.5 (2)
C6—N1—H1N	112.4 (19)	C11—C10—H10	119.3
O3—N2—O2	121.89 (17)	C9—C10—H10	119.3
O3—N2—O2	121.89 (17)	C10—C11—C6	120.8 (2)
O3—N2—C7	118.65 (17)	C10—C11—H11	119.6
O2—N2—C7	119.44 (17)	C6—C11—H11	119.6
O2—N2—C7	119.44 (17)	C13—C12—S2	112.66 (17)
C16—N3—C17	128.81 (18)	C13—C12—H12	123.7
C16—N3—H3N	118.3 (16)	S2—C12—H12	123.7
C17—N3—H3N	112.9 (16)	C12—C13—C14	112.9 (2)
O6—N4—O5	121.92 (18)	C12—C13—H13	123.5
O6—N4—O5	121.92 (18)	C14—C13—H13	123.5
O6—N4—C18	118.68 (18)	C15—C14—C13	110.71 (18)
O5—N4—C18	119.36 (17)	C15—C14—H14	124.6
O5—N4—C18	119.36 (17)	C13—C14—H14	124.6
C2—C1—S1	112.67 (17)	C14—C15—C16	130.68 (18)
C2—C1—H1	123.7	C14—C15—S2	111.69 (16)
S1—C1—H1	123.7	C16—C15—S2	117.62 (15)
C1—C2—C3	112.57 (19)	O4—C16—N3	124.8 (2)
C1—C2—H2	123.7	O4—C16—C15	122.12 (19)
C3—C2—H2	123.7	N3—C16—C15	113.07 (18)
C4—C3—C2	111.11 (18)	C22—C17—N3	121.89 (18)
C4—C3—H3	124.4	C22—C17—C18	117.21 (19)
C2—C3—H3	124.4	N3—C17—C18	120.89 (18)
C3—C4—C5	130.78 (18)	C19—C18—C17	121.45 (19)
C3—C4—S1	111.76 (15)	C19—C18—N4	116.11 (18)
C5—C4—S1	117.42 (15)	C17—C18—N4	122.44 (18)
O1—C5—N1	124.7 (2)	C20—C19—C18	120.1 (2)
O1—C5—C4	121.59 (19)	C20—C19—H19	119.9
N1—C5—C4	113.69 (17)	C18—C19—H19	119.9
N1—C6—C11	122.09 (18)	C19—C20—C21	119.1 (2)
N1—C6—C7	120.96 (18)	C19—C20—H20	120.4
C11—C6—C7	116.95 (18)	C21—C20—H20	120.4
C8—C7—C6	121.73 (19)	C22—C21—C20	121.1 (2)
C8—C7—N2	115.67 (18)	C22—C21—H21	119.4
C6—C7—N2	122.60 (18)	C20—C21—H21	119.4
C9—C8—C7	119.8 (2)	C21—C22—C17	121.0 (2)
C9—C8—H8	120.1	C21—C22—H22	119.5
C7—C8—H8	120.1	C17—C22—H22	119.5
O2—O2—N2—O3	0.0 (5)	N1—C6—C11—C10	179.5 (2)
O2—O2—N2—C7	0.0 (5)	C7—C6—C11—C10	0.1 (3)
O5—O5—N4—O6	0.00 (11)	C15—S2—C12—C13	0.07 (19)
O5—O5—N4—C18	0.00 (6)	S2—C12—C13—C14	0.1 (3)
C4—S1—C1—C2	0.65 (18)	C12—C13—C14—C15	−0.4 (3)
S1—C1—C2—C3	−0.3 (3)	C13—C14—C15—C16	178.9 (2)
C1—C2—C3—C4	−0.3 (3)	C13—C14—C15—S2	0.4 (2)
C2—C3—C4—C5	178.5 (2)	C12—S2—C15—C14	−0.27 (17)
C2—C3—C4—S1	0.8 (2)	C12—S2—C15—C16	−178.96 (17)
C1—S1—C4—C3	−0.82 (17)	C17—N3—C16—O4	−4.7 (4)
C1—S1—C4—C5	−178.85 (17)	C17—N3—C16—C15	175.74 (19)
C6—N1—C5—O1	5.4 (4)	C14—C15—C16—O4	−167.8 (2)
C6—N1—C5—C4	−174.01 (19)	S2—C15—C16—O4	10.6 (3)
C3—C4—C5—O1	−175.9 (2)	C14—C15—C16—N3	11.8 (3)
S1—C4—C5—O1	1.7 (3)	S2—C15—C16—N3	−169.80 (15)
C3—C4—C5—N1	3.6 (3)	C16—N3—C17—C22	−12.8 (3)
S1—C4—C5—N1	−178.86 (15)	C16—N3—C17—C18	168.7 (2)
C5—N1—C6—C11	−17.6 (3)	C22—C17—C18—C19	−1.1 (3)
C5—N1—C6—C7	161.8 (2)	N3—C17—C18—C19	177.51 (19)
N1—C6—C7—C8	−178.37 (19)	C22—C17—C18—N4	179.48 (19)
C11—C6—C7—C8	1.0 (3)	N3—C17—C18—N4	−1.9 (3)
N1—C6—C7—N2	1.9 (3)	O6—N4—C18—C19	15.1 (3)
C11—C6—C7—N2	−178.70 (19)	O5—N4—C18—C19	−162.99 (19)
O3—N2—C7—C8	14.5 (3)	O5—N4—C18—C19	−162.99 (19)
O2—N2—C7—C8	−163.90 (19)	O6—N4—C18—C17	−165.5 (2)
O2—N2—C7—C8	−163.90 (19)	O5—N4—C18—C17	16.5 (3)
O3—N2—C7—C6	−165.80 (19)	O5—N4—C18—C17	16.5 (3)
O2—N2—C7—C6	15.8 (3)	C17—C18—C19—C20	−0.1 (3)
O2—N2—C7—C6	15.8 (3)	N4—C18—C19—C20	179.4 (2)
C6—C7—C8—C9	−1.5 (3)	C18—C19—C20—C21	1.1 (3)
N2—C7—C8—C9	178.20 (19)	C19—C20—C21—C22	−1.0 (3)
C7—C8—C9—C10	0.8 (3)	C20—C21—C22—C17	−0.2 (3)
C8—C9—C10—C11	0.3 (3)	N3—C17—C22—C21	−177.4 (2)
C9—C10—C11—C6	−0.8 (3)	C18—C17—C22—C21	1.2 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O2	0.81 (3)	1.96 (3)	2.634 (2)	140 (3)
N3—H3N···O5	0.84 (2)	1.93 (2)	2.616 (2)	138 (2)
C1—H1···O4i	0.95	2.50	3.209 (3)	131
C8—H8···O5ii	0.95	2.52	3.248 (3)	133
C19—H19···O2iii	0.95	2.63	3.377 (3)	136
C11—H11···S2iii	0.95	2.92	3.732 (2)	144
C22—H22···S1ii	0.95	2.84	3.689 (2)	149
C12—H12···O1iv	0.95	2.47	3.198 (3)	133

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O2	0.81 (3)	1.96 (3)	2.634 (2)	140 (3)
N3—H3N⋯O5	0.84 (2)	1.93 (2)	2.616 (2)	138 (2)
C1—H1⋯O4i	0.95	2.50	3.209 (3)	131
C8—H8⋯O5ii	0.95	2.52	3.248 (3)	133
C19—H19⋯O2iii	0.95	2.63	3.377 (3)	136
C11—H11⋯S2iii	0.95	2.92	3.732 (2)	144
C22—H22⋯S1ii	0.95	2.84	3.689 (2)	149
C12—H12⋯O1iv	0.95	2.47	3.198 (3)	133

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .