Benzaldehyde thio-semicarbazone monohydrate.

In the title compound, C(8)H(9)N(3)S·H(2)O, intra-molecular N-H⋯N hydrogen bonding contributes to the mol-ecular conformation. Water mol-ecules are involved in inter-molecular N-H⋯O and O-H⋯S hydrogen bonds, which link the mol-ecules into ribbons extended along the a axis. Weak inter-molecular N-H⋯S hydrogen bonds link these ribbons into layers parallel to the ab plane with the phenyl rings pointing up and down.

Related literature

For related crystal structures, see Beraldo et al. (2004 ▶); Bondock et al. (2007 ▶); Jing et al. (2006 ▶).

Experimental

Crystal data

C8H9N3S·H2O

M = 197.26

Orthorhombic,

a = 6.1685 (10) Å

b = 7.6733 (12) Å

c = 21.131 (2) Å

V = 1000.2 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.29 mm−1

T = 298 (2) K

0.49 × 0.30 × 0.28 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.871, T max = 0.923

4749 measured reflections

1764 independent reflections

1438 reflections with I > 2σ(I)

R int = 0.065

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.105

S = 1.07

1764 reflections

118 parameters

H-atom parameters constrained

Δρmax = 0.24 e Å−3

Δρmin = −0.17 e Å−3

Absolute structure: Flack (1983 ▶), 689 Friedel pairs

Flack parameter: −0.05 (13)

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/S1600536808022769/cv2428sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808022769/cv2428Isup2.hkl

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

C8H9N3S·H2O	Dx = 1.310 Mg m−3
Mr = 197.26	Mo Kα radiation λ = 0.71073 Å
Orthorhombic, P212121	Cell parameters from 1572 reflections
a = 6.1685 (10) Å	θ = 2.8–22.5º
b = 7.6733 (12) Å	µ = 0.29 mm−1
c = 21.131 (2) Å	T = 298 (2) K
V = 1000.2 (2) Å3	Block, orange
Z = 4	0.49 × 0.30 × 0.28 mm
F000 = 416

Bruker SMART CCD area-detector diffractometer	1764 independent reflections
Radiation source: fine-focus sealed tube	1438 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.065
T = 298(2) K	θmax = 25.0º
φ and ω scans	θmin = 1.9º
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)	h = −7→7
Tmin = 0.871, Tmax = 0.924	k = −9→6
4749 measured reflections	l = −25→24

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.045	w = 1/[σ2(Fo2) + (0.0438P)2 + 0.0825P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.105	(Δ/σ)max < 0.001
S = 1.08	Δρmax = 0.25 e Å−3
1764 reflections	Δρmin = −0.17 e Å−3
118 parameters	Extinction correction: none
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983), 689 Friedel pairs
Secondary atom site location: difference Fourier map	Flack parameter: −0.05 (13)

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	0.5077 (4)	0.4006 (3)	0.35842 (11)	0.0430 (6)
N2	0.4610 (4)	0.4442 (3)	0.42017 (10)	0.0402 (6)
H2	0.5473	0.5107	0.4412	0.048*
N3	0.1572 (5)	0.2820 (4)	0.41293 (12)	0.0616 (9)
H3A	0.1923	0.2576	0.3746	0.074*
H3B	0.0400	0.2401	0.4289	0.074*
O1	0.2807 (3)	0.8582 (3)	0.51847 (12)	0.0681 (7)
H1A	0.2874	0.7483	0.5138	0.082*
H1B	0.4026	0.9030	0.5091	0.082*
S1	0.22368 (12)	0.43397 (10)	0.52322 (3)	0.0473 (3)
C1	0.2821 (5)	0.3831 (3)	0.44708 (14)	0.0398 (7)
C2	0.6891 (5)	0.4535 (4)	0.33743 (13)	0.0436 (7)
H2A	0.7840	0.5112	0.3645	0.052*
C3	0.7511 (4)	0.4251 (4)	0.27170 (12)	0.0412 (7)
C4	0.6111 (6)	0.3517 (4)	0.22810 (15)	0.0534 (9)
H4	0.4745	0.3146	0.2409	0.064*
C5	0.6728 (7)	0.3333 (5)	0.16566 (16)	0.0640 (11)
H5	0.5766	0.2870	0.1362	0.077*
C6	0.8751 (7)	0.3834 (5)	0.14733 (17)	0.0636 (11)
H6	0.9180	0.3671	0.1056	0.076*
C7	1.0158 (6)	0.4572 (5)	0.18932 (16)	0.0630 (10)
H7	1.1523	0.4940	0.1762	0.076*
C8	0.9527 (5)	0.4761 (4)	0.25132 (15)	0.0536 (9)
H8	1.0490	0.5248	0.2802	0.064*

	U11	U22	U33	U12	U13	U23
N1	0.0480 (15)	0.0477 (15)	0.0332 (13)	0.0000 (13)	0.0012 (12)	−0.0020 (11)
N2	0.0443 (14)	0.0422 (14)	0.0342 (12)	−0.0074 (14)	−0.0004 (11)	−0.0034 (12)
N3	0.061 (2)	0.079 (2)	0.0456 (17)	−0.0290 (17)	0.0118 (14)	−0.0121 (15)
O1	0.0524 (15)	0.0609 (13)	0.0910 (19)	0.0017 (12)	0.0204 (15)	−0.0130 (13)
S1	0.0467 (5)	0.0576 (5)	0.0376 (4)	0.0009 (4)	0.0015 (4)	−0.0018 (4)
C1	0.0402 (17)	0.0381 (16)	0.0411 (16)	0.0008 (15)	−0.0035 (15)	0.0036 (12)
C2	0.0415 (17)	0.0469 (17)	0.0422 (16)	0.0035 (17)	−0.0009 (14)	−0.0018 (14)
C3	0.0421 (17)	0.0433 (14)	0.0383 (15)	0.0013 (18)	0.0036 (14)	0.0015 (14)
C4	0.056 (2)	0.061 (2)	0.0429 (19)	−0.0134 (17)	0.0061 (17)	−0.0012 (17)
C5	0.083 (3)	0.065 (2)	0.044 (2)	−0.013 (2)	0.0033 (19)	−0.0067 (18)
C6	0.086 (3)	0.061 (2)	0.043 (2)	0.005 (2)	0.017 (2)	0.0038 (18)
C7	0.053 (2)	0.080 (3)	0.057 (2)	−0.002 (2)	0.0154 (18)	0.010 (2)
C8	0.050 (2)	0.066 (2)	0.0446 (17)	−0.0061 (17)	0.0023 (16)	0.0054 (16)

N1—C2	1.270 (3)	C3—C8	1.373 (4)
N1—N2	1.378 (3)	C3—C4	1.382 (4)
N2—C1	1.327 (3)	C4—C5	1.380 (4)
N2—H2	0.8600	C4—H4	0.9300
N3—C1	1.310 (4)	C5—C6	1.362 (5)
N3—H3A	0.8600	C5—H5	0.9300
N3—H3B	0.8600	C6—C7	1.364 (5)
O1—H1A	0.8499	C6—H6	0.9300
O1—H1B	0.8499	C7—C8	1.375 (5)
S1—C1	1.695 (3)	C7—H7	0.9300
C2—C3	1.457 (4)	C8—H8	0.9300
C2—H2A	0.9300
C2—N1—N2	115.9 (3)	C4—C3—C2	122.2 (3)
C1—N2—N1	119.6 (2)	C5—C4—C3	120.4 (3)
C1—N2—H2	120.2	C5—C4—H4	119.8
N1—N2—H2	120.2	C3—C4—H4	119.8
C1—N3—H3A	120.0	C6—C5—C4	119.7 (4)
C1—N3—H3B	120.0	C6—C5—H5	120.2
H3A—N3—H3B	120.0	C4—C5—H5	120.2
H1A—O1—H1B	109.4	C5—C6—C7	121.0 (3)
N3—C1—N2	117.6 (3)	C5—C6—H6	119.5
N3—C1—S1	122.3 (2)	C7—C6—H6	119.5
N2—C1—S1	120.1 (2)	C6—C7—C8	118.9 (3)
N1—C2—C3	121.1 (3)	C6—C7—H7	120.5
N1—C2—H2A	119.5	C8—C7—H7	120.5
C3—C2—H2A	119.5	C3—C8—C7	121.7 (3)
C8—C3—C4	118.2 (3)	C3—C8—H8	119.2
C8—C3—C2	119.6 (3)	C7—C8—H8	119.2

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3A···N1	0.86	2.26	2.613 (4)	105
N2—H2···O1i	0.86	1.95	2.805 (3)	171
N3—H3B···S1ii	0.86	2.57	3.423 (3)	170
O1—H1A···S1	0.85	2.45	3.276 (2)	164
O1—H1B···S1i	0.85	2.44	3.284 (2)	172

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3A⋯N1	0.86	2.26	2.613 (4)	105
N2—H2⋯O1i	0.86	1.95	2.805 (3)	171
N3—H3B⋯S1ii	0.86	2.57	3.423 (3)	170
O1—H1A⋯S1	0.85	2.45	3.276 (2)	164
O1—H1B⋯S1i	0.85	2.44	3.284 (2)	172

Symmetry codes: (i) ; (ii) .