4-Cyano-benzaldehyde thio-semi-carbazone.

The mol-ecule of the title compound, C(9)H(8)N(4)S, adopts an E configuration about both the C=N and C-NH 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 a 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 reference structural data, see: Sutton (1965 ▶).

Experimental

Crystal data

C9H8N4S

M = 204.26

Monoclinic,

a = 12.284 (6) Å

b = 8.209 (4) Å

c = 10.058 (3) Å

β = 92.20 (3)°

V = 1013.5 (8) Å3

Z = 4

Mo Kα radiation

μ = 0.28 mm−1

T = 291 (2) K

0.25 × 0.17 × 0.15 mm

Data collection

Rigaku Mercury2 diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ▶) T min = 0.94, T max = 0.96

10019 measured reflections

2309 independent reflections

1596 reflections with I > 2σ(I)

R int = 0.055

Refinement

R[F 2 > 2σ(F 2)] = 0.055

wR(F 2) = 0.109

S = 1.01

2309 reflections

127 parameters

H-atom parameters constrained

Δρmax = 0.17 e Å−3

Δρmin = −0.19 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/S1600536808041792/rz2264sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808041792/rz2264Isup2.hkl

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

C9H8N4S	F(000) = 424
Mr = 204.26	Dx = 1.339 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1740 reflections
a = 12.284 (6) Å	θ = 2.5–27.5°
b = 8.209 (4) Å	µ = 0.28 mm−1
c = 10.058 (3) Å	T = 291 K
β = 92.20 (3)°	Block, colourless
V = 1013.5 (8) Å3	0.25 × 0.17 × 0.15 mm
Z = 4

Rigaku Mercury2 diffractometer	2309 independent reflections
Radiation source: fine-focus sealed tube	1596 reflections with I > 2σ(I)
graphite	Rint = 0.055
Detector resolution: 13.6612 pixels mm-1	θmax = 27.5°, θmin = 3.0°
CCD_Profile_fitting scans	h = −15→15
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	k = −10→10
Tmin = 0.94, Tmax = 0.96	l = −12→13
10019 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)] = 0.055	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.109	H-atom parameters constrained
S = 1.01	w = 1/[σ2(Fo2) + (0.0258P)2 + 0.6908P] where P = (Fo2 + 2Fc2)/3
2309 reflections	(Δ/σ)max < 0.001
127 parameters	Δρmax = 0.17 e Å−3
0 restraints	Δρmin = −0.19 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	0.07786 (19)	0.5792 (3)	0.6753 (2)	0.0446 (6)
C2	0.18757 (19)	0.2982 (3)	0.4587 (2)	0.0454 (6)
H2	0.1575	0.2048	0.4946	0.054*
C3	0.26310 (18)	0.2841 (3)	0.3506 (2)	0.0426 (6)
C4	0.30116 (19)	0.1304 (3)	0.3163 (2)	0.0482 (6)
H4	0.2748	0.0384	0.3583	0.058*
C5	0.3781 (2)	0.1135 (3)	0.2198 (2)	0.0532 (7)
H5	0.4029	0.0108	0.1964	0.064*
C6	0.4175 (2)	0.2517 (3)	0.1588 (2)	0.0509 (6)
C7	0.3777 (2)	0.4058 (3)	0.1891 (2)	0.0541 (7)
H7	0.4028	0.4973	0.1452	0.065*
C8	0.3008 (2)	0.4214 (3)	0.2846 (2)	0.0500 (6)
H8	0.2740	0.5239	0.3052	0.060*
C9	0.5021 (2)	0.2377 (4)	0.0632 (3)	0.0616 (7)
N1	0.1138 (2)	0.7144 (3)	0.6221 (2)	0.0717 (8)
H1A	0.1485	0.7106	0.5496	0.086*
H1B	0.1026	0.8065	0.6600	0.086*
N2	0.09749 (15)	0.4384 (2)	0.61235 (17)	0.0436 (5)
H2A	0.0694	0.3490	0.6396	0.052*
N3	0.16254 (15)	0.4379 (2)	0.50426 (18)	0.0441 (5)
N4	0.5709 (2)	0.2293 (3)	−0.0102 (3)	0.0853 (9)
S1	0.01195 (6)	0.57476 (8)	0.81966 (6)	0.0544 (2)

	U11	U22	U33	U12	U13	U23
C1	0.0526 (14)	0.0390 (12)	0.0423 (12)	0.0019 (12)	0.0033 (11)	0.0001 (11)
C2	0.0475 (14)	0.0477 (14)	0.0414 (13)	−0.0021 (12)	0.0063 (11)	−0.0010 (11)
C3	0.0399 (13)	0.0479 (14)	0.0402 (12)	−0.0015 (11)	0.0030 (10)	−0.0042 (10)
C4	0.0505 (14)	0.0477 (14)	0.0467 (13)	−0.0025 (12)	0.0053 (12)	−0.0032 (11)
C5	0.0533 (15)	0.0568 (17)	0.0498 (14)	0.0051 (13)	0.0050 (12)	−0.0093 (12)
C6	0.0463 (14)	0.0659 (17)	0.0406 (13)	0.0036 (14)	0.0050 (11)	−0.0039 (13)
C7	0.0540 (15)	0.0593 (17)	0.0496 (14)	−0.0012 (14)	0.0094 (12)	0.0056 (13)
C8	0.0533 (15)	0.0469 (14)	0.0500 (14)	0.0026 (13)	0.0072 (11)	−0.0046 (12)
C9	0.0626 (17)	0.0696 (19)	0.0535 (15)	0.0057 (15)	0.0115 (14)	0.0018 (14)
N1	0.112 (2)	0.0411 (13)	0.0645 (15)	−0.0058 (13)	0.0407 (14)	−0.0043 (11)
N2	0.0546 (12)	0.0375 (11)	0.0396 (10)	0.0007 (10)	0.0111 (9)	−0.0008 (9)
N3	0.0492 (11)	0.0464 (12)	0.0372 (10)	0.0016 (10)	0.0068 (8)	−0.0027 (9)
N4	0.088 (2)	0.091 (2)	0.0797 (18)	0.0167 (17)	0.0398 (16)	0.0100 (16)
S1	0.0765 (5)	0.0431 (3)	0.0448 (3)	0.0083 (4)	0.0184 (3)	0.0010 (3)

C1—N1	1.316 (3)	C5—H5	0.9300
C1—N2	1.344 (3)	C6—C7	1.394 (4)
C1—S1	1.689 (2)	C6—C9	1.447 (3)
C2—N3	1.277 (3)	C7—C8	1.378 (3)
C2—C3	1.461 (3)	C7—H7	0.9300
C2—H2	0.9300	C8—H8	0.9300
C3—C4	1.394 (3)	C9—N4	1.146 (3)
C3—C8	1.396 (3)	N1—H1A	0.8600
C4—C5	1.387 (3)	N1—H1B	0.8600
C4—H4	0.9300	N2—N3	1.374 (2)
C5—C6	1.385 (4)	N2—H2A	0.8600
N1—C1—N2	117.7 (2)	C5—C6—C9	120.1 (3)
N1—C1—S1	123.15 (19)	C7—C6—C9	118.9 (2)
N2—C1—S1	119.15 (18)	C8—C7—C6	119.4 (2)
N3—C2—C3	120.5 (2)	C8—C7—H7	120.3
N3—C2—H2	119.8	C6—C7—H7	120.3
C3—C2—H2	119.8	C7—C8—C3	120.4 (2)
C4—C3—C8	119.5 (2)	C7—C8—H8	119.8
C4—C3—C2	119.0 (2)	C3—C8—H8	119.8
C8—C3—C2	121.4 (2)	N4—C9—C6	178.1 (3)
C5—C4—C3	120.5 (2)	C1—N1—H1A	120.0
C5—C4—H4	119.7	C1—N1—H1B	120.0
C3—C4—H4	119.7	H1A—N1—H1B	120.0
C6—C5—C4	119.1 (2)	C1—N2—N3	119.73 (19)
C6—C5—H5	120.4	C1—N2—H2A	120.1
C4—C5—H5	120.4	N3—N2—H2A	120.1
C5—C6—C7	121.0 (2)	C2—N3—N2	116.2 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···S1i	0.86	2.50	3.355 (2)	171
N1—H1B···S1ii	0.86	2.63	3.399 (3)	150

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯S1i	0.86	2.50	3.355 (2)	171
N1—H1B⋯S1ii	0.86	2.63	3.399 (3)	150

Symmetry codes: (i) ; (ii) .