Thio-phene-2-carbaldehyde 2,4-dinitro-phenyl-hydrazone.

In the approximately planar molecule of the title compound, C(11)H(8)N(4)O(4)S, the dihedral angle between the thio-phene and benzene rings is 5.73 (10)°. In the crystal structure, bifurcated inter/intra-molecular N-H⋯(O,O) hydrogen bonds are present. The intermolecular links lead to inversion dimers containing an R(2) (2)(12) graph-set motif.

Related literature

For general background, see: Okabe et al. (1993 ▶). For graph-set notation, see: Etter et al. (1990 ▶); Bernstein et al. (1995 ▶).

Experimental

Crystal data

C11H8N4O4S

M = 292.27

Monoclinic,

a = 4.8994 (17) Å

b = 9.520 (3) Å

c = 25.708 (8) Å

β = 92.71 (2)°

V = 1197.7 (7) Å3

Z = 4

Mo Kα radiation

μ = 0.29 mm−1

T = 291 (2) K

0.30 × 0.26 × 0.24 mm

Data collection

Bruker SMART APEX CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T min = 0.915, T max = 0.929

11010 measured reflections

2285 independent reflections

1718 reflections with I > 2σ(I)

R int = 0.047

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.087

S = 1.02

2285 reflections

184 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.16 e Å−3

Δρmin = −0.19 e Å−3

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL and PLATON (Spek, 2003 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808038397/dn2406sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808038397/dn2406Isup2.hkl

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

C11H8N4O4S	F000 = 600
Mr = 292.27	Dx = 1.621 Mg m−3
Monoclinic, P21/c	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5391 reflections
a = 4.8994 (17) Å	θ = 2.3–27.4º
b = 9.520 (3) Å	µ = 0.29 mm−1
c = 25.708 (8) Å	T = 291 (2) K
β = 92.71 (2)º	Block, purple
V = 1197.7 (7) Å3	0.30 × 0.26 × 0.24 mm
Z = 4

Bruker SMART APEX CCD diffractometer	2285 independent reflections
Radiation source: sealed tube	1718 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.047
T = 291(2) K	θmax = 26.0º
φ and ω scans	θmin = 1.6º
Absorption correction: multi-scan(SADABS; Bruker, 2000)	h = −6→5
Tmin = 0.915, Tmax = 0.929	k = −11→11
11010 measured reflections	l = −31→29

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)] = 0.045	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.087	w = 1/[σ2(Fo2) + (0.04P)2] where P = (Fo2 + 2Fc2)/3
S = 1.02	(Δ/σ)max < 0.001
2285 reflections	Δρmax = 0.16 e Å−3
184 parameters	Δρmin = −0.19 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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
C1	0.1154 (4)	0.2360 (2)	0.04553 (7)	0.0342 (4)
C2	−0.0759 (4)	0.1287 (2)	0.04720 (7)	0.0350 (4)
H2	−0.2010	0.1150	0.0193	0.042*
C3	−0.0801 (4)	0.04351 (18)	0.08984 (7)	0.0315 (4)
C4	0.1065 (4)	0.0673 (2)	0.13207 (7)	0.0383 (5)
H4	0.1048	0.0087	0.1610	0.046*
C5	0.2882 (4)	0.1738 (2)	0.13141 (7)	0.0350 (4)
H5	0.4096	0.1870	0.1599	0.042*
C6	0.2980 (4)	0.26512 (18)	0.08856 (7)	0.0291 (4)
C7	0.8165 (4)	0.49823 (19)	0.13079 (7)	0.0389 (5)
H7	0.7974	0.5614	0.1033	0.047*
C8	1.0163 (4)	0.52284 (19)	0.17283 (7)	0.0341 (4)
C9	1.1994 (5)	0.6353 (2)	0.17481 (8)	0.0418 (5)
H9	1.2066	0.7050	0.1496	0.050*
C10	1.3738 (5)	0.6289 (2)	0.22076 (9)	0.0465 (5)
H10	1.5107	0.6939	0.2290	0.056*
C11	1.3173 (5)	0.5174 (2)	0.25090 (8)	0.0522 (6)
H11	1.4113	0.4975	0.2823	0.063*
N1	0.0973 (4)	0.31477 (18)	0.00000 (6)	0.0394 (4)
N2	−0.2778 (4)	−0.06932 (17)	0.09065 (7)	0.0414 (4)
N3	0.4846 (4)	0.37052 (17)	0.08923 (6)	0.0378 (4)
H1	0.483 (5)	0.426 (2)	0.0624 (9)	0.045*
N4	0.6631 (3)	0.38663 (15)	0.13180 (6)	0.0321 (4)
O1	0.2484 (4)	0.41150 (16)	−0.00353 (6)	0.0545 (4)
O2	−0.0594 (3)	0.29004 (14)	−0.03604 (5)	0.0461 (4)
O3	−0.4272 (3)	−0.08987 (16)	0.05310 (6)	0.0526 (4)
O4	−0.2847 (3)	−0.13710 (15)	0.12986 (6)	0.0513 (4)
S1	1.05706 (12)	0.41736 (6)	0.22559 (2)	0.04762 (18)

	U11	U22	U33	U12	U13	U23
C1	0.0302 (10)	0.0438 (10)	0.0277 (10)	−0.0016 (8)	−0.0096 (8)	−0.0034 (7)
C2	0.0330 (10)	0.0410 (10)	0.0303 (10)	−0.0007 (8)	−0.0046 (8)	−0.0039 (7)
C3	0.0326 (10)	0.0290 (8)	0.0325 (9)	−0.0001 (7)	−0.0024 (8)	−0.0025 (7)
C4	0.0414 (12)	0.0417 (10)	0.0314 (10)	0.0038 (8)	−0.0038 (9)	0.0075 (8)
C5	0.0259 (10)	0.0463 (10)	0.0323 (10)	0.0090 (8)	−0.0035 (8)	−0.0005 (8)
C6	0.0270 (9)	0.0339 (8)	0.0262 (9)	0.0002 (7)	−0.0004 (7)	−0.0062 (7)
C7	0.0510 (12)	0.0394 (10)	0.0257 (9)	−0.0026 (9)	−0.0057 (8)	−0.0013 (8)
C8	0.0316 (10)	0.0353 (9)	0.0349 (9)	−0.0023 (8)	−0.0025 (8)	−0.0079 (7)
C9	0.0473 (13)	0.0361 (9)	0.0412 (11)	−0.0042 (9)	−0.0073 (9)	−0.0059 (8)
C10	0.0387 (12)	0.0416 (10)	0.0581 (14)	−0.0045 (9)	−0.0105 (10)	−0.0220 (10)
C11	0.0629 (15)	0.0558 (13)	0.0357 (11)	0.0052 (11)	−0.0222 (11)	−0.0131 (9)
N1	0.0383 (10)	0.0452 (9)	0.0335 (9)	−0.0104 (8)	−0.0120 (8)	−0.0013 (7)
N2	0.0360 (10)	0.0421 (9)	0.0453 (10)	−0.0026 (7)	−0.0074 (8)	0.0047 (8)
N3	0.0387 (10)	0.0443 (9)	0.0290 (9)	−0.0077 (7)	−0.0126 (7)	−0.0001 (7)
N4	0.0345 (8)	0.0344 (8)	0.0266 (8)	−0.0003 (6)	−0.0087 (7)	−0.0040 (6)
O1	0.0659 (11)	0.0525 (9)	0.0435 (9)	−0.0225 (8)	−0.0163 (8)	0.0158 (7)
O2	0.0471 (9)	0.0505 (8)	0.0383 (8)	−0.0317 (7)	−0.0222 (7)	0.0182 (6)
O3	0.0488 (10)	0.0534 (9)	0.0537 (9)	−0.0260 (7)	−0.0185 (8)	−0.0002 (7)
O4	0.0566 (10)	0.0451 (8)	0.0519 (9)	−0.0169 (7)	−0.0008 (8)	0.0131 (7)
S1	0.0480 (3)	0.0553 (3)	0.0385 (3)	−0.0071 (2)	−0.0093 (2)	0.0040 (2)

C1—C2	1.388 (3)	C8—C9	1.396 (3)
C1—N1	1.389 (2)	C8—S1	1.692 (2)
C1—C6	1.417 (2)	C9—C10	1.426 (3)
C2—C3	1.365 (3)	C9—H9	0.9300
C2—H2	0.9300	C10—C11	1.351 (3)
C3—C4	1.404 (2)	C10—H10	0.9300
C3—N2	1.447 (2)	C11—S1	1.696 (2)
C4—C5	1.350 (3)	C11—H11	0.9300
C4—H4	0.9300	N1—O1	1.188 (2)
C5—C6	1.406 (3)	N1—O2	1.1983 (19)
C5—H5	0.9300	N2—O4	1.199 (2)
C6—N3	1.357 (2)	N2—O3	1.199 (2)
C7—N4	1.302 (2)	N3—N4	1.377 (2)
C7—C8	1.442 (2)	N3—H1	0.87 (2)
C7—H7	0.9300
C2—C1—N1	114.01 (15)	C9—C8—S1	112.01 (14)
C2—C1—C6	121.47 (17)	C7—C8—S1	123.66 (14)
N1—C1—C6	124.40 (17)	C8—C9—C10	110.86 (19)
C3—C2—C1	119.87 (17)	C8—C9—H9	124.6
C3—C2—H2	120.1	C10—C9—H9	124.6
C1—C2—H2	120.1	C11—C10—C9	112.19 (18)
C2—C3—C4	119.41 (17)	C11—C10—H10	123.9
C2—C3—N2	119.22 (15)	C9—C10—H10	123.9
C4—C3—N2	121.36 (16)	C10—C11—S1	113.08 (15)
C5—C4—C3	121.14 (18)	C10—C11—H11	123.5
C5—C4—H4	119.4	S1—C11—H11	123.5
C3—C4—H4	119.4	O1—N1—O2	118.16 (16)
C4—C5—C6	121.43 (17)	O1—N1—C1	117.89 (14)
C4—C5—H5	119.3	O2—N1—C1	123.94 (16)
C6—C5—H5	119.3	O4—N2—O3	123.26 (17)
N3—C6—C5	119.70 (15)	O4—N2—C3	117.21 (15)
N3—C6—C1	123.69 (17)	O3—N2—C3	119.53 (16)
C5—C6—C1	116.55 (17)	C6—N3—N4	119.65 (16)
N4—C7—C8	119.31 (16)	C6—N3—H1	117.6 (14)
N4—C7—H7	120.3	N4—N3—H1	122.8 (14)
C8—C7—H7	120.3	C7—N4—N3	114.87 (15)
C9—C8—C7	124.33 (18)	C8—S1—C11	91.85 (11)
N1—C1—C2—C3	180.00 (18)	C8—C9—C10—C11	−0.6 (3)
C6—C1—C2—C3	−3.8 (3)	C9—C10—C11—S1	0.1 (3)
C1—C2—C3—C4	1.3 (3)	C2—C1—N1—O1	177.51 (19)
C1—C2—C3—N2	−178.99 (18)	C6—C1—N1—O1	1.5 (3)
C2—C3—C4—C5	0.6 (3)	C2—C1—N1—O2	−3.3 (3)
N2—C3—C4—C5	−179.16 (18)	C6—C1—N1—O2	−179.4 (2)
C3—C4—C5—C6	0.1 (3)	C2—C3—N2—O4	−176.10 (19)
C4—C5—C6—N3	−179.66 (19)	C4—C3—N2—O4	3.6 (3)
C4—C5—C6—C1	−2.5 (3)	C2—C3—N2—O3	3.1 (3)
C2—C1—C6—N3	−178.60 (18)	C4—C3—N2—O3	−177.21 (19)
N1—C1—C6—N3	−2.8 (3)	C5—C6—N3—N4	0.2 (3)
C2—C1—C6—C5	4.3 (3)	C1—C6—N3—N4	−176.76 (17)
N1—C1—C6—C5	−179.88 (19)	C8—C7—N4—N3	−178.20 (17)
N4—C7—C8—C9	177.13 (19)	C6—N3—N4—C7	−173.88 (18)
N4—C7—C8—S1	−2.5 (3)	C9—C8—S1—C11	−0.66 (18)
C7—C8—C9—C10	−178.8 (2)	C7—C8—S1—C11	179.01 (19)
S1—C8—C9—C10	0.8 (2)	C10—C11—S1—C8	0.3 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H1···O1i	0.87 (2)	2.57 (2)	3.338 (2)	148.2 (19)
N3—H1···O1	0.87 (2)	2.01 (2)	2.630 (2)	127.4 (19)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H1⋯O1i	0.87 (2)	2.57 (2)	3.338 (2)	148.2 (19)
N3—H1⋯O1	0.87 (2)	2.01 (2)	2.630 (2)	127.4 (19)

Symmetry code: (i) .