(E)-1-(2,4-Dinitro-phen-yl)-2-[1-(thio-phen-2-yl)ethyl-idene]hydrazine.

The mol-ecule of the title compound, C(12)H(10)N(4)O(4)S, is slightly twisted, with a dihedral angle of 8.23 (9)° between the benzene and thio-phene rings. One nitro group is co-planar [O-N-C-C torsion angles = -0.5 (3) and -1.9 (3)°] whereas the other is slightly twisted with respect to the benzene ring [O-N-C-C torsion angles = -5.1 (3) and -5.7 (3)°]. In the crystal, the mol-ecules are linked by weak C-H⋯O inter-actions into screw chains along the b axis. The mol-ecular conformation is consolidated by an intra-molecular N-H⋯O hydrogen bond.

Related literature

For bond-length data, see: Allen et al. (1987 ▶). For related structures, see: Chantrapromma et al. (2010 ▶); Fun et al. (2010 ▶); Jansrisewangwong et al. (2010 ▶); Shan et al. (2008 ▶). For background to and the biological activity of hydrazones, see: Baughman et al. (2004 ▶); Bedia et al. (2006 ▶); El-Tabl et al. (2008) ▶; Ramamohan et al. (1995 ▶); Rollas & Küçükgüzel (2007 ▶). For the stability of the temperature controller used in the data collection, see Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C12H10N4O4S

M = 306.30

Monoclinic,

a = 9.4868 (5) Å

b = 15.3912 (8) Å

c = 8.9756 (4) Å

β = 91.672 (2)°

V = 1310.00 (11) Å3

Z = 4

Mo Kα radiation

μ = 0.27 mm−1

T = 100 K

0.60 × 0.19 × 0.16 mm

Data collection

Bruker APEXII CCD area detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.854, T max = 0.959

10366 measured reflections

2414 independent reflections

2176 reflections with I > 2σ(I)

R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.109

S = 1.08

2414 reflections

195 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.38 e Å−3

Δρmin = −0.44 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811011135/rz2573sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811011135/rz2573Isup2.hkl

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

C12H10N4O4S	F(000) = 632
Mr = 306.30	Dx = 1.553 Mg m−3
Monoclinic, P21/c	Melting point = 516–518 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 9.4868 (5) Å	Cell parameters from 2414 reflections
b = 15.3912 (8) Å	θ = 2.2–25.5°
c = 8.9756 (4) Å	µ = 0.27 mm−1
β = 91.672 (2)°	T = 100 K
V = 1310.00 (11) Å3	Block, orange
Z = 4	0.60 × 0.19 × 0.16 mm

Bruker APEXII CCD area detector diffractometer	2414 independent reflections
Radiation source: sealed tube	2176 reflections with I > 2σ(I)
graphite	Rint = 0.027
φ and ω scans	θmax = 25.5°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −10→11
Tmin = 0.854, Tmax = 0.959	k = −18→14
10366 measured reflections	l = −10→10

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.109	H atoms treated by a mixture of independent and constrained refinement
S = 1.08	w = 1/[σ2(Fo2) + (0.0504P)2 + 1.3252P] where P = (Fo2 + 2Fc2)/3
2414 reflections	(Δ/σ)max < 0.001
195 parameters	Δρmax = 0.38 e Å−3
0 restraints	Δρmin = −0.44 e Å−3

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 120.0 (1) K.

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	0.18528 (6)	0.07603 (4)	1.08312 (6)	0.02114 (18)
O1	0.38055 (16)	0.48642 (10)	0.89817 (17)	0.0234 (4)
O2	0.5358 (2)	0.53354 (10)	0.7464 (2)	0.0367 (5)
O3	0.82477 (16)	0.34691 (11)	0.46978 (17)	0.0263 (4)
O4	0.82742 (17)	0.20890 (11)	0.51711 (18)	0.0295 (4)
N1	0.29668 (17)	0.24567 (11)	1.00495 (18)	0.0165 (4)
N2	0.35684 (18)	0.31993 (13)	0.9518 (2)	0.0169 (4)
H1N2	0.328 (2)	0.3673 (18)	0.967 (3)	0.018 (6)*
N3	0.47704 (19)	0.47362 (12)	0.8097 (2)	0.0219 (4)
N4	0.78273 (18)	0.28269 (13)	0.53639 (19)	0.0212 (4)
C1	0.4601 (2)	0.31302 (13)	0.8510 (2)	0.0150 (4)
C2	0.5214 (2)	0.38567 (13)	0.7812 (2)	0.0165 (4)
C3	0.6272 (2)	0.37572 (14)	0.6779 (2)	0.0185 (5)
H3A	0.6662	0.4239	0.6322	0.022*
C4	0.6724 (2)	0.29369 (14)	0.6451 (2)	0.0170 (4)
C5	0.6148 (2)	0.22010 (14)	0.7110 (2)	0.0169 (4)
H5A	0.6469	0.1649	0.6866	0.020*
C6	0.5112 (2)	0.23004 (13)	0.8115 (2)	0.0158 (4)
H6A	0.4731	0.1810	0.8553	0.019*
C7	0.2011 (2)	0.25572 (14)	1.1041 (2)	0.0166 (4)
C8	0.1380 (2)	0.17563 (14)	1.1560 (2)	0.0173 (4)
C9	0.0380 (2)	0.16528 (15)	1.2632 (2)	0.0202 (5)
H9A	−0.0017	0.2113	1.3144	0.024*
C10	0.0020 (2)	0.07644 (14)	1.2874 (2)	0.0188 (5)
H10A	−0.0628	0.0581	1.3565	0.023*
C11	0.0736 (2)	0.02170 (16)	1.1973 (2)	0.0237 (5)
H11A	0.0630	−0.0384	1.1977	0.028*
C12	0.1551 (2)	0.34159 (14)	1.1648 (2)	0.0211 (5)
H12A	0.2364	0.3740	1.1986	0.032*
H12B	0.0941	0.3321	1.2468	0.032*
H12C	0.1054	0.3736	1.0880	0.032*

	U11	U22	U33	U12	U13	U23
S1	0.0239 (3)	0.0203 (3)	0.0198 (3)	−0.0021 (2)	0.0103 (2)	−0.0022 (2)
O1	0.0255 (8)	0.0191 (8)	0.0262 (8)	0.0024 (6)	0.0095 (7)	−0.0037 (6)
O2	0.0487 (11)	0.0151 (9)	0.0478 (11)	−0.0032 (8)	0.0247 (9)	0.0050 (8)
O3	0.0254 (8)	0.0333 (10)	0.0206 (8)	−0.0092 (7)	0.0095 (6)	0.0043 (7)
O4	0.0300 (9)	0.0300 (10)	0.0297 (9)	0.0039 (7)	0.0190 (7)	−0.0033 (7)
N1	0.0174 (8)	0.0171 (9)	0.0152 (8)	−0.0018 (7)	0.0052 (7)	−0.0004 (7)
N2	0.0190 (9)	0.0125 (10)	0.0194 (9)	0.0006 (8)	0.0072 (7)	−0.0015 (7)
N3	0.0272 (10)	0.0163 (10)	0.0225 (9)	−0.0019 (8)	0.0058 (8)	0.0020 (8)
N4	0.0188 (9)	0.0277 (11)	0.0174 (9)	−0.0020 (8)	0.0063 (7)	−0.0013 (8)
C1	0.0150 (9)	0.0188 (11)	0.0113 (9)	−0.0003 (8)	0.0024 (7)	−0.0001 (8)
C2	0.0181 (10)	0.0142 (10)	0.0173 (10)	−0.0011 (8)	0.0035 (8)	−0.0003 (8)
C3	0.0205 (10)	0.0188 (11)	0.0162 (10)	−0.0045 (9)	0.0026 (8)	0.0037 (8)
C4	0.0160 (10)	0.0234 (12)	0.0120 (9)	−0.0024 (9)	0.0075 (8)	0.0008 (8)
C5	0.0182 (10)	0.0173 (11)	0.0152 (10)	0.0023 (8)	0.0029 (8)	−0.0026 (8)
C6	0.0182 (10)	0.0147 (10)	0.0148 (9)	−0.0012 (8)	0.0048 (8)	0.0009 (8)
C7	0.0172 (10)	0.0199 (11)	0.0127 (9)	0.0008 (8)	0.0020 (8)	−0.0018 (8)
C8	0.0160 (10)	0.0216 (12)	0.0143 (10)	0.0004 (8)	0.0031 (8)	−0.0027 (8)
C9	0.0187 (10)	0.0261 (12)	0.0163 (10)	0.0004 (9)	0.0065 (8)	−0.0025 (9)
C10	0.0168 (10)	0.0256 (12)	0.0146 (10)	−0.0032 (9)	0.0094 (8)	0.0001 (9)
C11	0.0251 (11)	0.0236 (12)	0.0229 (11)	−0.0064 (9)	0.0076 (9)	0.0018 (9)
C12	0.0228 (11)	0.0219 (12)	0.0191 (11)	0.0001 (9)	0.0093 (9)	−0.0025 (9)

S1—C11	1.714 (2)	C3—H3A	0.9300
S1—C8	1.731 (2)	C4—C5	1.396 (3)
O1—N3	1.245 (2)	C5—C6	1.362 (3)
O2—N3	1.226 (2)	C5—H5A	0.9300
O3—N4	1.228 (2)	C6—H6A	0.9300
O4—N4	1.226 (2)	C7—C8	1.453 (3)
N1—C7	1.298 (3)	C7—C12	1.499 (3)
N1—N2	1.370 (3)	C8—C9	1.380 (3)
N2—C1	1.357 (3)	C9—C10	1.428 (3)
N2—H1N2	0.79 (3)	C9—H9A	0.9300
N3—C2	1.443 (3)	C10—C11	1.363 (3)
N4—C4	1.462 (3)	C10—H10A	0.9300
C1—C2	1.415 (3)	C11—H11A	0.9300
C1—C6	1.415 (3)	C12—H12A	0.9600
C2—C3	1.394 (3)	C12—H12B	0.9600
C3—C4	1.368 (3)	C12—H12C	0.9600
C11—S1—C8	91.98 (11)	C4—C5—H5A	120.4
C7—N1—N2	116.47 (18)	C5—C6—C1	121.80 (19)
C1—N2—N1	118.89 (18)	C5—C6—H6A	119.1
C1—N2—H1N2	116.4 (18)	C1—C6—H6A	119.1
N1—N2—H1N2	124.2 (18)	N1—C7—C8	114.90 (19)
O2—N3—O1	121.94 (18)	N1—C7—C12	124.81 (19)
O2—N3—C2	119.03 (18)	C8—C7—C12	120.30 (18)
O1—N3—C2	119.03 (17)	C9—C8—C7	128.3 (2)
O4—N4—O3	123.94 (18)	C9—C8—S1	110.63 (16)
O4—N4—C4	117.31 (18)	C7—C8—S1	121.11 (15)
O3—N4—C4	118.75 (18)	C8—C9—C10	112.89 (19)
N2—C1—C2	123.19 (19)	C8—C9—H9A	123.6
N2—C1—C6	119.84 (18)	C10—C9—H9A	123.6
C2—C1—C6	116.98 (18)	C11—C10—C9	112.11 (19)
C3—C2—C1	121.38 (19)	C11—C10—H10A	123.9
C3—C2—N3	116.11 (18)	C9—C10—H10A	123.9
C1—C2—N3	122.50 (18)	C10—C11—S1	112.39 (18)
C4—C3—C2	118.73 (19)	C10—C11—H11A	123.8
C4—C3—H3A	120.6	S1—C11—H11A	123.8
C2—C3—H3A	120.6	C7—C12—H12A	109.5
C3—C4—C5	121.90 (19)	C7—C12—H12B	109.5
C3—C4—N4	119.07 (19)	H12A—C12—H12B	109.5
C5—C4—N4	119.03 (19)	C7—C12—H12C	109.5
C6—C5—C4	119.21 (19)	H12A—C12—H12C	109.5
C6—C5—H5A	120.4	H12B—C12—H12C	109.5
C7—N1—N2—C1	178.22 (17)	C3—C4—C5—C6	−0.4 (3)
N1—N2—C1—C2	175.14 (17)	N4—C4—C5—C6	−179.49 (17)
N1—N2—C1—C6	−4.9 (3)	C4—C5—C6—C1	0.0 (3)
N2—C1—C2—C3	−179.90 (18)	N2—C1—C6—C5	−179.89 (18)
C6—C1—C2—C3	0.2 (3)	C2—C1—C6—C5	0.1 (3)
N2—C1—C2—N3	−1.2 (3)	N2—N1—C7—C8	178.99 (16)
C6—C1—C2—N3	178.88 (17)	N2—N1—C7—C12	−1.1 (3)
O2—N3—C2—C3	−1.9 (3)	N1—C7—C8—C9	177.69 (19)
O1—N3—C2—C3	178.29 (17)	C12—C7—C8—C9	−2.2 (3)
O2—N3—C2—C1	179.28 (19)	N1—C7—C8—S1	−2.2 (2)
O1—N3—C2—C1	−0.5 (3)	C12—C7—C8—S1	177.89 (15)
C1—C2—C3—C4	−0.5 (3)	C11—S1—C8—C9	−0.67 (16)
N3—C2—C3—C4	−179.26 (17)	C11—S1—C8—C7	179.21 (17)
C2—C3—C4—C5	0.6 (3)	C7—C8—C9—C10	−178.97 (19)
C2—C3—C4—N4	179.69 (17)	S1—C8—C9—C10	0.9 (2)
O4—N4—C4—C3	175.19 (18)	C8—C9—C10—C11	−0.7 (3)
O3—N4—C4—C3	−5.1 (3)	C9—C10—C11—S1	0.2 (2)
O4—N4—C4—C5	−5.7 (3)	C8—S1—C11—C10	0.27 (17)
O3—N4—C4—C5	174.08 (18)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H1N2···O1	0.79 (3)	2.00 (3)	2.618 (3)	134 (2)
C6—H6A···O2i	0.93	2.45	3.099 (3)	127
C9—H9A···O4ii	0.93	2.47	3.147 (2)	129
C11—H11A···O3i	0.93	2.57	3.240 (3)	129

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H1N2⋯O1	0.79 (3)	2.00 (3)	2.618 (3)	134 (2)
C6—H6A⋯O2i	0.93	2.45	3.099 (3)	127
C9—H9A⋯O4ii	0.93	2.47	3.147 (2)	129
C11—H11A⋯O3i	0.93	2.57	3.240 (3)	129

Symmetry codes: (i) ; (ii) .