3-Nitro-benzaldehyde thio-semicarbazone.

The mol-ecule of the title compound, C(8)H(8)N(4)O(2)S, adopts an E configuration about both the C-N bonds. In the crystal structure, adjacent mol-ecules are linked by inter-molecular N-H⋯S hydrogen-bonding inter-actions, forming chains running parallel to the b axis.

Related literature

For general background to thio­semicarbazone compounds, see: Casas et al. (2000 ▶); Tarafder et al. (2000 ▶); Deschamps et al. (2003 ▶); Liu et al. (1999 ▶); Wu et al. (2000 ▶). For similar structures, see: Sutton (1965 ▶).

Experimental

Crystal data

C8H8N4O2S

M = 224.25

Monoclinic,

a = 13.276 (3) Å

b = 8.225 (7) Å

c = 10.491 (4) Å

β = 112.78 (5)°

V = 1056.2 (11) Å3

Z = 4

Mo Kα radiation

μ = 0.29 mm−1

T = 291 (2) K

0.20 × 0.20 × 0.20 mm

Data collection

Rigaku Mercury2 diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ▶) T min = 0.930, T max = 0.940

9317 measured reflections

2071 independent reflections

1343 reflections with I > 2σ(I)

R int = 0.081

Refinement

R[F 2 > 2σ(F 2)] = 0.069

wR(F 2) = 0.117

S = 1.01

2071 reflections

136 parameters

H-atom parameters constrained

Δρmax = 0.23 e Å−3

Δρmin = −0.18 e Å−3

Data collection: CrystalClear (Rigaku, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808042645/rz2279sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808042645/rz2279Isup2.hkl

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

C8H8N4O2S	F(000) = 464
Mr = 224.25	Dx = 1.410 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1712 reflections
a = 13.276 (3) Å	θ = 3.0–27.4°
b = 8.225 (7) Å	µ = 0.29 mm−1
c = 10.491 (4) Å	T = 291 K
β = 112.78 (5)°	Block, yellow
V = 1056.2 (11) Å3	0.20 × 0.20 × 0.20 mm
Z = 4

Rigaku Mercury2 diffractometer	2071 independent reflections
Radiation source: fine-focus sealed tube	1343 reflections with I > 2σ(I)
graphite	Rint = 0.081
Detector resolution: 13.6612 pixels mm-1	θmax = 26.0°, θmin = 3.0°
CCD_Profile_fitting scans	h = −16→16
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	k = −10→10
Tmin = 0.930, Tmax = 0.940	l = −12→12
9317 measured reflections

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)] = 0.069	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.117	H-atom parameters constrained
S = 1.01	w = 1/[σ2(Fo2) + (0.0122P)2 + 1.5479P] where P = (Fo2 + 2Fc2)/3
2071 reflections	(Δ/σ)max < 0.001
136 parameters	Δρmax = 0.23 e Å−3
0 restraints	Δρmin = −0.18 e Å−3

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	0.9248 (3)	1.1141 (4)	1.1340 (3)	0.0416 (8)
C2	0.8132 (3)	0.8365 (4)	0.8634 (3)	0.0444 (9)
H2A	0.8406	0.7429	0.9149	0.053*
C3	0.7415 (3)	0.8218 (4)	0.7163 (3)	0.0412 (9)
C4	0.7111 (3)	0.6666 (4)	0.6615 (3)	0.0441 (9)
H4A	0.7375	0.5743	0.7153	0.053*
C5	0.6401 (3)	0.6545 (5)	0.5237 (4)	0.0476 (10)
C6	0.5984 (3)	0.7864 (5)	0.4403 (4)	0.0584 (11)
H6A	0.5501	0.7733	0.3490	0.070*
C7	0.6301 (3)	0.9401 (5)	0.4955 (4)	0.0603 (12)
H7A	0.6036	1.0314	0.4404	0.072*
C8	0.7017 (3)	0.9588 (5)	0.6334 (4)	0.0512 (10)
H8A	0.7229	1.0622	0.6697	0.061*
N1	0.8999 (3)	1.2497 (4)	1.0619 (3)	0.0572 (10)
H1A	0.8691	1.2460	0.9732	0.069*
H1B	0.9145	1.3420	1.1036	0.069*
N2	0.9000 (2)	0.9732 (3)	1.0633 (3)	0.0425 (8)
H2B	0.9222	0.8823	1.1055	0.051*
N3	0.8385 (2)	0.9751 (3)	0.9216 (3)	0.0411 (7)
N4	0.6100 (3)	0.4887 (5)	0.4659 (4)	0.0656 (10)
O1	0.6466 (3)	0.3718 (4)	0.5411 (4)	0.0905 (11)
O2	0.5489 (3)	0.4772 (5)	0.3440 (3)	0.1039 (13)
S1	0.98388 (9)	1.10945 (12)	1.30902 (9)	0.0529 (3)

	U11	U22	U33	U12	U13	U23
C1	0.046 (2)	0.038 (2)	0.0381 (19)	−0.0034 (18)	0.0136 (17)	0.0019 (17)
C2	0.048 (2)	0.041 (2)	0.0373 (19)	0.0029 (18)	0.0093 (17)	0.0012 (17)
C3	0.045 (2)	0.044 (2)	0.0326 (18)	−0.0016 (17)	0.0121 (17)	−0.0025 (16)
C4	0.043 (2)	0.047 (2)	0.041 (2)	0.0013 (17)	0.0138 (18)	−0.0016 (17)
C5	0.038 (2)	0.056 (3)	0.047 (2)	−0.0044 (18)	0.0144 (18)	−0.0142 (19)
C6	0.048 (3)	0.077 (3)	0.040 (2)	0.003 (2)	0.007 (2)	−0.008 (2)
C7	0.063 (3)	0.061 (3)	0.046 (2)	0.016 (2)	0.010 (2)	0.009 (2)
C8	0.054 (3)	0.047 (2)	0.045 (2)	0.0008 (19)	0.0120 (19)	−0.0025 (18)
N1	0.084 (3)	0.0394 (19)	0.0371 (17)	−0.0042 (17)	0.0120 (18)	−0.0012 (14)
N2	0.054 (2)	0.0345 (17)	0.0332 (16)	−0.0005 (14)	0.0102 (15)	−0.0003 (13)
N3	0.0443 (19)	0.0418 (18)	0.0335 (15)	−0.0040 (14)	0.0110 (14)	−0.0023 (13)
N4	0.056 (3)	0.076 (3)	0.063 (3)	−0.017 (2)	0.022 (2)	−0.029 (2)
O1	0.107 (3)	0.056 (2)	0.095 (3)	−0.016 (2)	0.024 (2)	−0.0196 (19)
O2	0.104 (3)	0.110 (3)	0.069 (2)	−0.028 (2)	0.003 (2)	−0.042 (2)
S1	0.0735 (7)	0.0436 (5)	0.0345 (5)	−0.0028 (5)	0.0130 (5)	−0.0035 (4)

C1—N1	1.316 (4)	C6—C7	1.386 (5)
C1—N2	1.346 (4)	C6—H6A	0.9300
C1—S1	1.695 (3)	C7—C8	1.398 (5)
C2—N3	1.276 (4)	C7—H7A	0.9300
C2—C3	1.471 (4)	C8—H8A	0.9300
C2—H2A	0.9300	N1—H1A	0.8600
C3—C4	1.394 (5)	N1—H1B	0.8600
C3—C8	1.396 (5)	N2—N3	1.392 (4)
C4—C5	1.391 (5)	N2—H2B	0.8600
C4—H4A	0.9300	N4—O1	1.219 (5)
C5—C6	1.369 (5)	N4—O2	1.225 (4)
C5—N4	1.483 (5)
N1—C1—N2	117.4 (3)	C7—C6—H6A	120.9
N1—C1—S1	123.3 (3)	C6—C7—C8	120.5 (4)
N2—C1—S1	119.3 (3)	C6—C7—H7A	119.8
N3—C2—C3	121.3 (3)	C8—C7—H7A	119.8
N3—C2—H2A	119.4	C3—C8—C7	119.9 (4)
C3—C2—H2A	119.4	C3—C8—H8A	120.1
C4—C3—C8	120.2 (3)	C7—C8—H8A	120.1
C4—C3—C2	118.3 (3)	C1—N1—H1A	120.0
C8—C3—C2	121.5 (3)	C1—N1—H1B	120.0
C5—C4—C3	117.8 (3)	H1A—N1—H1B	120.0
C5—C4—H4A	121.1	C1—N2—N3	119.7 (3)
C3—C4—H4A	121.1	C1—N2—H2B	120.1
C6—C5—C4	123.5 (4)	N3—N2—H2B	120.1
C6—C5—N4	119.3 (3)	C2—N3—N2	116.0 (3)
C4—C5—N4	117.2 (4)	O1—N4—O2	123.5 (4)
C5—C6—C7	118.3 (4)	O1—N4—C5	118.9 (3)
C5—C6—H6A	120.9	O2—N4—C5	117.6 (4)
N3—C2—C3—C4	−175.8 (4)	C2—C3—C8—C7	−177.4 (4)
N3—C2—C3—C8	2.5 (6)	C6—C7—C8—C3	−0.1 (6)
C8—C3—C4—C5	−0.6 (5)	N1—C1—N2—N3	−7.7 (5)
C2—C3—C4—C5	177.7 (3)	S1—C1—N2—N3	171.4 (2)
C3—C4—C5—C6	−0.4 (6)	C3—C2—N3—N2	175.3 (3)
C3—C4—C5—N4	178.9 (3)	C1—N2—N3—C2	−176.1 (3)
C4—C5—C6—C7	1.1 (6)	C6—C5—N4—O1	−179.3 (4)
N4—C5—C6—C7	−178.2 (4)	C4—C5—N4—O1	1.3 (6)
C5—C6—C7—C8	−0.8 (6)	C6—C5—N4—O2	0.5 (6)
C4—C3—C8—C7	0.9 (6)	C4—C5—N4—O2	−178.9 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1B···S1i	0.86	2.56	3.369 (4)	158
N2—H2B···S1ii	0.86	2.56	3.394 (4)	165

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1B⋯S1i	0.86	2.56	3.369 (4)	158
N2—H2B⋯S1ii	0.86	2.56	3.394 (4)	165

Symmetry codes: (i) ; (ii) .