Pyridine-2-carbaldehyde thio-semi-carbazone.

The asymmetric unit of the title compound, C(7)H(8)N(4)S, contains two independent mol-ecules with slightly different conformations; the dihedral angles between the pyridine ring and mean plane of the thio-semicarbazone unit in the two mol-ecules are 2.88 (5) and 6.30 (5)°. Inter-molecular N-H⋯N and N-H⋯S hydrogen bonds link the mol-ecules into layers parallel to the ab plane.

Related literature

For the properties of thio­semicarbazones, see: Beraldo & Gambino (2004 ▶). For the crystal structure of a related compound, see: Gu et al. (2008 ▶).

Experimental

Crystal data

C7H8N4S

M = 180.23

Orthorhombic,

a = 20.725 (2) Å

b = 4.7857 (6) Å

c = 17.393 (2) Å

V = 1725.1 (4) Å3

Z = 8

Mo Kα radiation

μ = 0.32 mm−1

T = 298 (2) K

0.45 × 0.20 × 0.19 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.868, T max = 0.941

7296 measured reflections

2797 independent reflections

1951 reflections with I > 2σ(I)

R int = 0.059

Refinement

R[F 2 > 2σ(F 2)] = 0.066

wR(F 2) = 0.165

S = 0.96

2797 reflections

218 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.97 e Å−3

Δρmin = −0.96 e Å−3

Absolute structure: Flack (1983 ▶), 1218 Friedel pairs

Flack parameter: 0.02 (19)

Data collection: SMART (Siemens, 1996 ▶); cell refinement: SAINT (Siemens, 1996 ▶); data reduction: SAINT; 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/S1600536809001962/cv2504sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809001962/cv2504Isup2.hkl

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

C7H8N4S	Dx = 1.388 Mg m−3
Mr = 180.23	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pna21	Cell parameters from 1607 reflections
a = 20.725 (2) Å	θ = 2.3–21.6°
b = 4.7857 (6) Å	µ = 0.32 mm−1
c = 17.393 (2) Å	T = 298 K
V = 1725.1 (4) Å3	Block, orange
Z = 8	0.45 × 0.20 × 0.19 mm
F(000) = 752

Bruker SMART CCD area-detector diffractometer	2797 independent reflections
Radiation source: fine-focus sealed tube	1951 reflections with I > 2σ(I)
graphite	Rint = 0.059
φ and ω scans	θmax = 25.0°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −24→20
Tmin = 0.868, Tmax = 0.941	k = −5→5
7296 measured reflections	l = −20→17

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)] = 0.066	H-atom parameters constrained
wR(F2) = 0.165	w = 1/[σ2(Fo2) + (0.0511P)2 + 6.2026P] where P = (Fo2 + 2Fc2)/3
S = 0.96	(Δ/σ)max = 0.001
2797 reflections	Δρmax = 0.97 e Å−3
218 parameters	Δρmin = −0.96 e Å−3
1 restraint	Absolute structure: Flack (1983), 1218 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.02 (19)

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
N8	0.6201 (3)	−0.1518 (12)	0.5432 (3)	0.0387 (14)
N1	0.5188 (3)	0.9637 (13)	0.4216 (3)	0.0405 (15)
H1	0.5464	0.9533	0.4584	0.049*
N2	0.5264 (3)	0.8019 (12)	0.3566 (3)	0.0385 (14)
N3	0.4295 (3)	1.1564 (14)	0.3672 (3)	0.0514 (18)
H3A	0.4376	1.0591	0.3267	0.062*
H3B	0.3965	1.2651	0.3682	0.062*
N4	0.6451 (3)	0.3132 (13)	0.2989 (3)	0.0443 (15)
N5	0.7451 (3)	0.5151 (13)	0.4275 (3)	0.0411 (14)
H5	0.7213	0.4881	0.3877	0.049*
N6	0.7334 (3)	0.3664 (12)	0.4937 (3)	0.0371 (14)
N7	0.8267 (3)	0.7425 (15)	0.4879 (4)	0.0493 (17)
H7A	0.8170	0.6506	0.5288	0.059*
H7B	0.8580	0.8603	0.4885	0.059*
S1	0.45768 (9)	1.3182 (4)	0.50951 (10)	0.0483 (5)
S2	0.80649 (9)	0.8767 (4)	0.34251 (11)	0.0480 (5)
C1	0.4677 (3)	1.1390 (15)	0.4274 (4)	0.0352 (16)
C2	0.5761 (3)	0.6438 (14)	0.3561 (4)	0.0383 (17)
H2	0.6046	0.6495	0.3975	0.046*
C3	0.5892 (3)	0.4557 (14)	0.2926 (4)	0.0362 (16)
C4	0.5478 (3)	0.4143 (16)	0.2310 (4)	0.0438 (18)
H4	0.5097	0.5157	0.2272	0.053*
C5	0.5637 (4)	0.2228 (17)	0.1758 (5)	0.054 (2)
H5A	0.5367	0.1944	0.1338	0.064*
C6	0.6199 (4)	0.0727 (17)	0.1829 (5)	0.054 (2)
H6	0.6310	−0.0623	0.1468	0.065*
C7	0.6591 (4)	0.1270 (17)	0.2447 (4)	0.049 (2)
H7	0.6976	0.0283	0.2488	0.058*
C8	0.7935 (3)	0.7027 (15)	0.4244 (4)	0.0365 (17)
C9	0.6886 (3)	0.1868 (15)	0.4895 (4)	0.0383 (18)
H9	0.6667	0.1636	0.4432	0.046*
C10	0.6706 (3)	0.0160 (14)	0.5554 (4)	0.0351 (16)
C11	0.7028 (4)	0.0259 (17)	0.6248 (4)	0.049 (2)
H11	0.7375	0.1461	0.6317	0.058*
C12	0.6825 (4)	−0.1454 (17)	0.6836 (5)	0.053 (2)
H12	0.7030	−0.1408	0.7311	0.063*
C13	0.6313 (3)	−0.3245 (16)	0.6709 (4)	0.0471 (19)
H13	0.6166	−0.4438	0.7093	0.057*
C14	0.6029 (3)	−0.3205 (17)	0.6003 (5)	0.047 (2)
H14	0.5691	−0.4445	0.5914	0.057*

	U11	U22	U33	U12	U13	U23
N8	0.044 (3)	0.040 (3)	0.033 (3)	0.004 (3)	−0.004 (3)	0.003 (3)
N1	0.044 (3)	0.044 (4)	0.033 (3)	0.003 (3)	−0.006 (3)	−0.004 (3)
N2	0.043 (3)	0.039 (3)	0.034 (4)	−0.002 (3)	−0.003 (3)	−0.001 (3)
N3	0.049 (4)	0.064 (4)	0.041 (4)	0.013 (3)	−0.013 (3)	−0.018 (3)
N4	0.043 (3)	0.050 (4)	0.040 (4)	0.002 (3)	−0.005 (3)	−0.002 (3)
N5	0.048 (4)	0.047 (4)	0.029 (3)	0.001 (3)	−0.002 (3)	−0.003 (3)
N6	0.042 (3)	0.037 (3)	0.032 (4)	−0.001 (3)	−0.003 (2)	−0.007 (3)
N7	0.053 (3)	0.057 (4)	0.038 (4)	0.014 (3)	−0.003 (3)	−0.013 (3)
S1	0.0529 (10)	0.0535 (11)	0.0384 (11)	0.0042 (10)	−0.0040 (9)	−0.0095 (10)
S2	0.0506 (10)	0.0558 (11)	0.0377 (10)	0.0049 (10)	−0.0046 (9)	−0.0140 (10)
C1	0.035 (4)	0.034 (4)	0.037 (4)	−0.006 (3)	0.003 (3)	0.001 (3)
C2	0.040 (4)	0.040 (4)	0.034 (4)	0.000 (3)	−0.003 (3)	0.001 (3)
C3	0.043 (4)	0.033 (4)	0.033 (4)	0.001 (3)	0.003 (3)	−0.001 (3)
C4	0.040 (4)	0.050 (5)	0.041 (4)	0.010 (4)	−0.010 (3)	−0.003 (4)
C5	0.058 (5)	0.061 (5)	0.042 (5)	0.000 (5)	−0.014 (4)	−0.004 (4)
C6	0.070 (5)	0.056 (5)	0.038 (5)	0.003 (4)	0.002 (4)	−0.008 (4)
C7	0.044 (4)	0.058 (5)	0.044 (5)	0.008 (4)	0.005 (4)	−0.002 (4)
C8	0.034 (4)	0.037 (4)	0.038 (4)	−0.010 (3)	0.000 (3)	−0.004 (3)
C9	0.043 (4)	0.039 (4)	0.033 (4)	0.001 (3)	−0.003 (3)	−0.002 (3)
C10	0.039 (4)	0.034 (4)	0.033 (4)	0.000 (3)	−0.005 (3)	0.001 (3)
C11	0.050 (4)	0.056 (5)	0.040 (5)	0.008 (4)	−0.011 (3)	−0.006 (4)
C12	0.060 (5)	0.067 (6)	0.031 (4)	−0.006 (4)	−0.011 (4)	−0.006 (4)
C13	0.048 (4)	0.052 (5)	0.042 (5)	0.001 (4)	0.000 (3)	−0.013 (4)
C14	0.041 (4)	0.050 (5)	0.050 (5)	0.003 (4)	−0.002 (3)	0.003 (4)

N8—C14	1.328 (9)	C2—C3	1.450 (9)
N8—C10	1.336 (8)	C2—H2	0.9300
N1—C1	1.354 (8)	C3—C4	1.388 (9)
N1—N2	1.380 (8)	C4—C5	1.367 (10)
N1—H1	0.8600	C4—H4	0.9300
N2—C2	1.278 (8)	C5—C6	1.373 (10)
N3—C1	1.316 (9)	C5—H5A	0.9300
N3—H3A	0.8600	C6—C7	1.372 (10)
N3—H3B	0.8600	C6—H6	0.9300
N4—C7	1.330 (9)	C7—H7	0.9300
N4—C3	1.348 (8)	C9—C10	1.458 (10)
N5—C8	1.347 (8)	C9—H9	0.9300
N5—N6	1.375 (8)	C10—C11	1.379 (9)
N5—H5	0.8600	C11—C12	1.376 (11)
N6—C9	1.267 (9)	C11—H11	0.9300
N7—C8	1.314 (9)	C12—C13	1.382 (10)
N7—H7A	0.8600	C12—H12	0.9300
N7—H7B	0.8600	C13—C14	1.362 (10)
S1—C1	1.679 (7)	C13—H13	0.9300
S2—C8	1.671 (8)	C14—H14	0.9300
C14—N8—C10	117.2 (6)	C4—C5—H5A	120.3
C1—N1—N2	119.9 (6)	C6—C5—H5A	120.3
C1—N1—H1	120.1	C7—C6—C5	118.3 (7)
N2—N1—H1	120.1	C7—C6—H6	120.8
C2—N2—N1	115.5 (6)	C5—C6—H6	120.8
C1—N3—H3A	120.0	N4—C7—C6	123.5 (7)
C1—N3—H3B	120.0	N4—C7—H7	118.2
H3A—N3—H3B	120.0	C6—C7—H7	118.2
C7—N4—C3	118.0 (6)	N7—C8—N5	116.9 (7)
C8—N5—N6	120.7 (6)	N7—C8—S2	124.0 (6)
C8—N5—H5	119.7	N5—C8—S2	119.1 (5)
N6—N5—H5	119.7	N6—C9—C10	121.4 (7)
C9—N6—N5	115.6 (6)	N6—C9—H9	119.3
C8—N7—H7A	120.0	C10—C9—H9	119.3
C8—N7—H7B	120.0	N8—C10—C11	122.6 (7)
H7A—N7—H7B	120.0	N8—C10—C9	114.3 (6)
N3—C1—N1	116.8 (6)	C11—C10—C9	123.1 (7)
N3—C1—S1	124.8 (6)	C12—C11—C10	118.8 (7)
N1—C1—S1	118.5 (5)	C12—C11—H11	120.6
N2—C2—C3	121.5 (6)	C10—C11—H11	120.6
N2—C2—H2	119.2	C11—C12—C13	119.0 (7)
C3—C2—H2	119.2	C11—C12—H12	120.5
N4—C3—C4	121.4 (6)	C13—C12—H12	120.5
N4—C3—C2	114.4 (6)	C14—C13—C12	117.8 (8)
C4—C3—C2	124.2 (6)	C14—C13—H13	121.1
C5—C4—C3	119.3 (7)	C12—C13—H13	121.1
C5—C4—H4	120.4	N8—C14—C13	124.5 (8)
C3—C4—H4	120.4	N8—C14—H14	117.8
C4—C5—C6	119.5 (7)	C13—C14—H14	117.8

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···N8i	0.86	2.18	3.032 (8)	169
N3—H3B···S2ii	0.86	2.57	3.417 (6)	168
N7—H7B···S1iii	0.86	2.60	3.455 (7)	172
N5—H5···N4	0.86	2.36	3.199 (8)	164

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯N8i	0.86	2.18	3.032 (8)	169
N3—H3B⋯S2ii	0.86	2.57	3.417 (6)	168
N7—H7B⋯S1iii	0.86	2.60	3.455 (7)	172
N5—H5⋯N4	0.86	2.36	3.199 (8)	164

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