Benzaldehyde thio-semicarbazone.

The title compound, C(8)H(9)N(3)S, contains two mol-ecules in the asymmetric unit. One mol-ecule is close to being planar (r.m.s. deviation from the mean plane = 0.06 Å for the non-H atoms), while the other exhibits a dihedral angle of 21.7 (1)° between the benzene ring and the mean plane of the thio-semicarbazone unit. Inter-molecular N-H⋯S hydrogen bonds link the mol-ecules into layers parallel to the (010) plane.

Related literature

For background literature concerning aryl­hydrazone compounds, see: Beraldo & Gambino (2004 ▶); Bondock et al. (2007 ▶). For the related 2,4-dichloro­benzyl­idene compound, see: Jing et al. (2006 ▶).

Experimental

Crystal data

C8H9N3S

M = 179.24

Triclinic,

a = 5.8692 (13) Å

b = 12.513 (2) Å

c = 13.519 (2) Å

α = 112.735 (3)°

β = 95.384 (2)°

γ = 96.153 (2)°

V = 900.4 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.31 mm−1

T = 298 (2) K

0.24 × 0.13 × 0.10 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.930, T max = 0.970

4740 measured reflections

3124 independent reflections

1846 reflections with I > 2σ(I)

R int = 0.039

Refinement

R[F 2 > 2σ(F 2)] = 0.058

wR(F 2) = 0.162

S = 0.95

3124 reflections

217 parameters

H-atom parameters constrained

Δρmax = 0.31 e Å−3

Δρmin = −0.27 e Å−3

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/S1600536808038270/bi2310sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808038270/bi2310Isup2.hkl

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

C8H9N3S	Z = 4
Mr = 179.24	F000 = 376
Triclinic, P1	Dx = 1.322 Mg m−3
Hall symbol: -P 1	Mo Kα radiation λ = 0.71073 Å
a = 5.8692 (13) Å	Cell parameters from 1310 reflections
b = 12.513 (2) Å	θ = 2.9–25.0º
c = 13.519 (2) Å	µ = 0.31 mm−1
α = 112.735 (3)º	T = 298 (2) K
β = 95.384 (2)º	Block, orange
γ = 96.153 (2)º	0.24 × 0.13 × 0.10 mm
V = 900.4 (3) Å3

Bruker SMART CCD area-detector diffractometer	3124 independent reflections
Radiation source: fine-focus sealed tube	1846 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.039
T = 298(2) K	θmax = 25.0º
φ and ω scans	θmin = 1.7º
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)	h = −6→6
Tmin = 0.930, Tmax = 0.970	k = −12→14
4740 measured reflections	l = −16→14

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)] = 0.058	H-atom parameters constrained
wR(F2) = 0.162	w = 1/[σ2(Fo2) + (0.0856P)2] where P = (Fo2 + 2Fc2)/3
S = 0.95	(Δ/σ)max < 0.001
3124 reflections	Δρmax = 0.31 e Å−3
217 parameters	Δρmin = −0.27 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
N1	0.9674 (5)	0.8260 (3)	0.9684 (2)	0.0484 (8)
N2	1.1667 (5)	0.8822 (3)	0.9512 (2)	0.0504 (8)
H2	1.2934	0.8999	0.9956	0.061*
N3	0.9536 (5)	0.8863 (3)	0.8034 (2)	0.0550 (9)
H3A	0.8331	0.8563	0.8208	0.066*
H3B	0.9414	0.9020	0.7467	0.066*
N4	0.3374 (5)	0.7659 (3)	0.4823 (2)	0.0486 (8)
N5	0.4649 (5)	0.8653 (3)	0.5625 (2)	0.0518 (8)
H5	0.4200	0.8950	0.6249	0.062*
N6	0.7036 (6)	0.8737 (3)	0.4423 (3)	0.0612 (10)
H6A	0.6092	0.8166	0.3930	0.073*
H6B	0.8262	0.9031	0.4259	0.073*
S1	1.40293 (17)	0.96409 (10)	0.83250 (8)	0.0561 (3)
S2	0.83277 (19)	1.02721 (9)	0.64490 (8)	0.0610 (4)
C1	0.9813 (7)	0.8063 (3)	1.0543 (3)	0.0500 (9)
H1	1.1169	0.8341	1.1040	0.060*
C2	0.7837 (7)	0.7398 (3)	1.0749 (3)	0.0493 (10)
C3	0.5747 (7)	0.7039 (3)	1.0076 (3)	0.0569 (10)
H3	0.5566	0.7229	0.9475	0.068*
C4	0.3920 (8)	0.6403 (4)	1.0277 (4)	0.0660 (12)
H4	0.2516	0.6167	0.9814	0.079*
C5	0.4178 (9)	0.6118 (4)	1.1169 (4)	0.0700 (13)
H5A	0.2950	0.5690	1.1309	0.084*
C6	0.6255 (9)	0.6472 (4)	1.1845 (4)	0.0675 (12)
H6	0.6431	0.6283	1.2447	0.081*
C7	0.8081 (8)	0.7104 (3)	1.1640 (3)	0.0584 (11)
H7	0.9486	0.7336	1.2100	0.070*
C8	1.1574 (6)	0.9084 (3)	0.8637 (3)	0.0438 (9)
C9	0.1484 (7)	0.7251 (3)	0.5034 (3)	0.0484 (9)
H9	0.0969	0.7658	0.5687	0.058*
C10	0.0129 (6)	0.6152 (3)	0.4263 (3)	0.0455 (9)
C11	−0.2018 (7)	0.5775 (4)	0.4462 (4)	0.0607 (11)
H11	−0.2622	0.6246	0.5065	0.073*
C12	−0.3267 (8)	0.4700 (4)	0.3766 (4)	0.0695 (13)
H12	−0.4716	0.4453	0.3898	0.083*
C13	−0.2378 (9)	0.4002 (4)	0.2889 (4)	0.0736 (13)
H13	−0.3205	0.3270	0.2435	0.088*
C14	−0.0287 (9)	0.4368 (4)	0.2671 (4)	0.0730 (13)
H14	0.0287	0.3893	0.2060	0.088*
C15	0.0981 (7)	0.5436 (3)	0.3350 (3)	0.0576 (11)
H15	0.2410	0.5680	0.3198	0.069*
C16	0.6604 (6)	0.9162 (3)	0.5434 (3)	0.0443 (9)

	U11	U22	U33	U12	U13	U23
N1	0.0460 (19)	0.0479 (18)	0.0522 (19)	0.0088 (15)	0.0119 (15)	0.0195 (15)
N2	0.0434 (18)	0.056 (2)	0.0511 (19)	0.0056 (15)	0.0037 (15)	0.0225 (16)
N3	0.0415 (19)	0.072 (2)	0.0521 (19)	−0.0021 (16)	0.0018 (16)	0.0296 (17)
N4	0.0452 (19)	0.0479 (18)	0.0471 (18)	−0.0024 (15)	0.0008 (15)	0.0170 (15)
N5	0.048 (2)	0.0513 (19)	0.0488 (19)	−0.0080 (15)	0.0049 (15)	0.0170 (15)
N6	0.055 (2)	0.063 (2)	0.055 (2)	−0.0165 (17)	0.0107 (17)	0.0171 (17)
S1	0.0434 (6)	0.0700 (7)	0.0494 (6)	0.0008 (5)	0.0081 (5)	0.0196 (5)
S2	0.0595 (7)	0.0634 (7)	0.0504 (6)	−0.0189 (5)	−0.0037 (5)	0.0224 (5)
C1	0.054 (2)	0.046 (2)	0.049 (2)	0.0123 (19)	0.0080 (19)	0.0165 (18)
C2	0.060 (3)	0.039 (2)	0.047 (2)	0.0102 (19)	0.014 (2)	0.0133 (17)
C3	0.058 (3)	0.057 (3)	0.056 (2)	0.012 (2)	0.004 (2)	0.023 (2)
C4	0.054 (3)	0.060 (3)	0.082 (3)	0.013 (2)	0.011 (2)	0.024 (2)
C5	0.078 (3)	0.053 (3)	0.083 (3)	0.010 (2)	0.033 (3)	0.028 (2)
C6	0.088 (4)	0.058 (3)	0.060 (3)	0.011 (3)	0.021 (3)	0.026 (2)
C7	0.071 (3)	0.048 (2)	0.050 (2)	0.004 (2)	0.006 (2)	0.0163 (19)
C8	0.044 (2)	0.043 (2)	0.040 (2)	0.0094 (17)	0.0079 (18)	0.0112 (17)
C9	0.044 (2)	0.050 (2)	0.051 (2)	0.0031 (18)	0.0108 (18)	0.0215 (18)
C10	0.039 (2)	0.044 (2)	0.054 (2)	0.0005 (16)	0.0022 (17)	0.0224 (18)
C11	0.049 (2)	0.062 (3)	0.074 (3)	−0.001 (2)	0.013 (2)	0.032 (2)
C12	0.047 (3)	0.070 (3)	0.094 (4)	−0.012 (2)	−0.001 (2)	0.043 (3)
C13	0.078 (3)	0.048 (3)	0.081 (3)	−0.012 (2)	−0.015 (3)	0.022 (2)
C14	0.078 (3)	0.062 (3)	0.066 (3)	0.002 (3)	0.005 (3)	0.015 (2)
C15	0.052 (2)	0.053 (2)	0.063 (3)	0.000 (2)	0.007 (2)	0.020 (2)
C16	0.044 (2)	0.044 (2)	0.048 (2)	−0.0003 (17)	0.0004 (18)	0.0248 (18)

N1—C1	1.274 (5)	C3—H3	0.930
N1—N2	1.385 (4)	C4—C5	1.384 (6)
N2—C8	1.342 (5)	C4—H4	0.930
N2—H2	0.860	C5—C6	1.371 (7)
N3—C8	1.320 (5)	C5—H5A	0.930
N3—H3A	0.860	C6—C7	1.377 (6)
N3—H3B	0.860	C6—H6	0.930
N4—C9	1.274 (5)	C7—H7	0.930
N4—N5	1.375 (4)	C9—C10	1.453 (5)
N5—C16	1.347 (4)	C9—H9	0.930
N5—H5	0.860	C10—C11	1.385 (5)
N6—C16	1.321 (4)	C10—C15	1.390 (5)
N6—H6A	0.860	C11—C12	1.383 (6)
N6—H6B	0.860	C11—H11	0.930
S1—C8	1.693 (4)	C12—C13	1.362 (6)
S2—C16	1.674 (4)	C12—H12	0.930
C1—C2	1.466 (5)	C13—C14	1.362 (6)
C1—H1	0.930	C13—H13	0.930
C2—C3	1.375 (5)	C14—C15	1.376 (6)
C2—C7	1.388 (5)	C14—H14	0.930
C3—C4	1.377 (6)	C15—H15	0.930
C1—N1—N2	116.5 (3)	C7—C6—H6	119.8
C8—N2—N1	118.4 (3)	C6—C7—C2	120.4 (4)
C8—N2—H2	120.8	C6—C7—H7	119.8
N1—N2—H2	120.8	C2—C7—H7	119.8
C8—N3—H3A	120.0	N3—C8—N2	117.6 (3)
C8—N3—H3B	120.0	N3—C8—S1	122.5 (3)
H3A—N3—H3B	120.0	N2—C8—S1	119.9 (3)
C9—N4—N5	117.1 (3)	N4—C9—C10	120.4 (4)
C16—N5—N4	120.0 (3)	N4—C9—H9	119.8
C16—N5—H5	120.0	C10—C9—H9	119.8
N4—N5—H5	120.0	C11—C10—C15	118.8 (4)
C16—N6—H6A	120.0	C11—C10—C9	119.6 (4)
C16—N6—H6B	120.0	C15—C10—C9	121.6 (3)
H6A—N6—H6B	120.0	C12—C11—C10	120.1 (4)
N1—C1—C2	120.0 (4)	C12—C11—H11	119.9
N1—C1—H1	120.0	C10—C11—H11	119.9
C2—C1—H1	120.0	C13—C12—C11	120.1 (4)
C3—C2—C7	118.8 (4)	C13—C12—H12	119.9
C3—C2—C1	121.9 (4)	C11—C12—H12	119.9
C7—C2—C1	119.3 (4)	C14—C13—C12	120.5 (4)
C2—C3—C4	121.0 (4)	C14—C13—H13	119.8
C2—C3—H3	119.5	C12—C13—H13	119.8
C4—C3—H3	119.5	C13—C14—C15	120.4 (5)
C3—C4—C5	119.8 (5)	C13—C14—H14	119.8
C3—C4—H4	120.1	C15—C14—H14	119.8
C5—C4—H4	120.1	C14—C15—C10	120.1 (4)
C6—C5—C4	119.7 (4)	C14—C15—H15	119.9
C6—C5—H5A	120.2	C10—C15—H15	119.9
C4—C5—H5A	120.2	N6—C16—N5	116.4 (3)
C5—C6—C7	120.4 (4)	N6—C16—S2	123.6 (3)
C5—C6—H6	119.8	N5—C16—S2	120.0 (3)
C1—N1—N2—C8	−177.7 (3)	N1—N2—C8—S1	−173.6 (2)
C9—N4—N5—C16	−176.7 (3)	N5—N4—C9—C10	−175.1 (3)
N2—N1—C1—C2	−175.6 (3)	N4—C9—C10—C11	−174.2 (4)
N1—C1—C2—C3	−4.5 (6)	N4—C9—C10—C15	8.9 (6)
N1—C1—C2—C7	174.5 (4)	C15—C10—C11—C12	0.6 (6)
C7—C2—C3—C4	0.2 (6)	C9—C10—C11—C12	−176.4 (4)
C1—C2—C3—C4	179.3 (4)	C10—C11—C12—C13	0.8 (7)
C2—C3—C4—C5	0.0 (6)	C11—C12—C13—C14	−1.9 (7)
C3—C4—C5—C6	0.0 (6)	C12—C13—C14—C15	1.7 (7)
C4—C5—C6—C7	−0.2 (7)	C13—C14—C15—C10	−0.2 (7)
C5—C6—C7—C2	0.4 (6)	C11—C10—C15—C14	−0.9 (6)
C3—C2—C7—C6	−0.4 (6)	C9—C10—C15—C14	176.0 (4)
C1—C2—C7—C6	−179.5 (3)	N4—N5—C16—N6	7.6 (5)
N1—N2—C8—N3	4.7 (5)	N4—N5—C16—S2	−172.6 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···S1i	0.86	2.64	3.443 (3)	155
N3—H3A···S1ii	0.86	2.98	3.488 (3)	120
N5—H5···S1ii	0.86	2.61	3.441 (3)	162
N6—H6B···S2iii	0.86	2.51	3.368 (3)	173

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯S1i	0.86	2.64	3.443 (3)	155
N3—H3A⋯S1ii	0.86	2.98	3.488 (3)	120
N5—H5⋯S1ii	0.86	2.61	3.441 (3)	162
N6—H6B⋯S2iii	0.86	2.51	3.368 (3)	173

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