(E)-2-[(1H-Imidazol-4-yl)methyl-idene]hydrazinecarbo-thio-amide monohydrate.

In the title compound, C5H7N5S·H2O, the main mol-ecule is approximately planar, with a maximum deviation from the mean plane through the non-H atoms of 0.1478 (12) Å for the amine N atom. In the crystal, the components are connected via N-H⋯O, N-H⋯S and O-H⋯N hydrogen bonds, forming a three-dimensional network.

Related literature

For the biological activity of thio­simecarbazone derivatives, see: Finch et al. (2000 ▶). For the crystal structures of related compounds, see: Alomar et al. (2013 ▶).

Experimental

Crystal data

C5H7N5S·H2O

M = 187.23

Monoclinic,

a = 10.8734 (5) Å

b = 11.2416 (5) Å

c = 7.0822 (3) Å

β = 75.601 (2)°

V = 838.50 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.35 mm−1

T = 150 K

0.4 × 0.23 × 0.16 mm

Data collection

Bruker APEXII CCD diffractometer

6537 measured reflections

1903 independent reflections

1726 reflections with I > 2σ(I)

R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.030

wR(F 2) = 0.083

S = 1.06

1903 reflections

127 parameters

H-atom parameters not refined

Δρmax = 0.38 e Å−3

Δρmin = −0.22 e Å−3

Data collection: APEX2 (Bruker, 2006 ▶); cell refinement: SAINT (Bruker, 2006 ▶); data reduction: SAINT; program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1999 ▶); software used to prepare material for publication: WinGX publication routines (Farrugia, 2012 ▶) and CRYSCAL (T. Roisnel, local program).

Crystal structure: contains datablock(s) I, publication_text. DOI: 10.1107/S1600536813022927/lh5642sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813022927/lh5642Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813022927/lh5642Isup3.docx

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813022927/lh5642Isup4.cml

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

C5H7N5S·H2O	Dx = 1.483 Mg m−3
Mr = 187.23	Melting point: 0 K
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 10.8734 (5) Å	Cell parameters from 3274 reflections
b = 11.2416 (5) Å	θ = 2.7–27.5°
c = 7.0822 (3) Å	µ = 0.35 mm−1
β = 75.601 (2)°	T = 150 K
V = 838.50 (6) Å3	Prism, colourless
Z = 4	0.4 × 0.23 × 0.16 mm
F(000) = 392

Bruker APEXII CCD diffractometer	Rint = 0.031
Graphite monochromator	θmax = 27.5°, θmin = 3.5°
CCD rotation images, thin slices scans	h = −13→14
6537 measured reflections	k = −14→13
1903 independent reflections	l = −9→9
1726 reflections with I > 2σ(I)

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)] = 0.030	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.083	H-atom parameters not refined
S = 1.06	w = 1/[σ2(Fo2) + (0.0438P)2 + 0.2645P] where P = (Fo2 + 2Fc2)/3
1903 reflections	(Δ/σ)max = 0.003
127 parameters	Δρmax = 0.38 e Å−3
0 restraints	Δρmin = −0.22 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
S1	−0.87437 (3)	0.64372 (3)	0.33879 (5)	0.02064 (13)
N1	−0.66924 (10)	0.51441 (11)	0.17680 (17)	0.0192 (3)
H1A	−0.6294 (19)	0.443 (2)	0.140 (3)	0.05*
H1B	−0.6319 (19)	0.583 (2)	0.135 (3)	0.05*
C2	−0.79042 (12)	0.51613 (11)	0.27634 (18)	0.0154 (3)
N3	−0.84841 (10)	0.41073 (10)	0.32669 (17)	0.0177 (2)
H3	−0.928 (2)	0.408 (2)	0.406 (3)	0.05*
N4	−0.77834 (10)	0.30715 (10)	0.28202 (16)	0.0170 (2)
C5	−0.84105 (12)	0.21003 (12)	0.32281 (19)	0.0168 (3)
H5	−0.9299	0.2125	0.38	0.02*
C6	−0.77714 (12)	0.09669 (12)	0.28214 (18)	0.0165 (3)
C7	−0.82981 (13)	−0.01458 (12)	0.3055 (2)	0.0203 (3)
H7	−0.9172	−0.0336	0.3521	0.024*
N8	−0.73164 (11)	−0.09260 (11)	0.24822 (17)	0.0214 (3)
H8	−0.743 (2)	−0.172 (2)	0.251 (3)	0.05*
C9	−0.62411 (13)	−0.02867 (13)	0.1925 (2)	0.0218 (3)
H9	−0.5421	−0.0627	0.1467	0.026*
N10	−0.64591 (10)	0.08743 (10)	0.20915 (17)	0.0191 (3)
O21	−0.50826 (10)	0.29013 (9)	−0.04044 (17)	0.0250 (2)
H21A	−0.552 (2)	0.3077 (19)	−0.118 (3)	0.05*
H21B	−0.552 (2)	0.237 (2)	0.038 (3)	0.05*

	U11	U22	U33	U12	U13	U23
S1	0.01797 (19)	0.01144 (19)	0.0285 (2)	0.00167 (11)	0.00184 (13)	0.00089 (13)
N1	0.0159 (5)	0.0133 (6)	0.0254 (6)	−0.0002 (4)	0.0004 (4)	0.0000 (5)
C2	0.0159 (6)	0.0146 (6)	0.0152 (6)	0.0002 (5)	−0.0030 (4)	−0.0003 (5)
N3	0.0154 (5)	0.0117 (6)	0.0224 (6)	0.0018 (4)	0.0025 (4)	−0.0001 (4)
N4	0.0174 (5)	0.0131 (6)	0.0185 (6)	0.0028 (4)	−0.0009 (4)	−0.0010 (4)
C5	0.0158 (6)	0.0158 (7)	0.0178 (6)	−0.0005 (5)	−0.0022 (5)	−0.0003 (5)
C6	0.0171 (6)	0.0162 (7)	0.0158 (6)	−0.0002 (5)	−0.0030 (5)	−0.0002 (5)
C7	0.0207 (6)	0.0163 (7)	0.0230 (7)	−0.0019 (5)	−0.0034 (5)	−0.0006 (5)
N8	0.0279 (6)	0.0114 (6)	0.0240 (6)	−0.0005 (5)	−0.0046 (5)	−0.0013 (5)
C9	0.0224 (7)	0.0167 (7)	0.0240 (7)	0.0032 (5)	−0.0015 (5)	−0.0012 (5)
N10	0.0177 (5)	0.0139 (6)	0.0233 (6)	0.0013 (4)	−0.0006 (4)	−0.0001 (4)
O21	0.0221 (5)	0.0221 (6)	0.0298 (6)	−0.0038 (4)	−0.0047 (4)	0.0068 (4)

S1—C2	1.6986 (13)	C6—C7	1.3685 (18)
N1—C2	1.3309 (17)	C6—N10	1.3955 (16)
N1—H1A	0.92 (2)	C7—N8	1.3630 (18)
N1—H1B	0.88 (2)	C7—H7	0.95
C2—N3	1.3480 (17)	N8—C9	1.3453 (18)
N3—N4	1.3844 (15)	N8—H8	0.90 (2)
N3—H3	0.90 (2)	C9—N10	1.3264 (18)
N4—C5	1.2816 (17)	C9—H9	0.95
C5—C6	1.4456 (18)	O21—H21A	0.83 (2)
C5—H5	0.95	O21—H21B	0.87 (2)
C2—N1—H1A	119.8 (13)	C7—C6—C5	127.99 (12)
C2—N1—H1B	118.5 (14)	N10—C6—C5	122.42 (12)
H1A—N1—H1B	121.2 (19)	N8—C7—C6	106.20 (12)
N1—C2—N3	117.63 (12)	N8—C7—H7	126.9
N1—C2—S1	123.18 (10)	C6—C7—H7	126.9
N3—C2—S1	119.18 (10)	C9—N8—C7	107.62 (12)
C2—N3—N4	118.96 (11)	C9—N8—H8	129.8 (14)
C2—N3—H3	120.5 (14)	C7—N8—H8	122.6 (14)
N4—N3—H3	119.7 (14)	N10—C9—N8	112.12 (12)
C5—N4—N3	115.68 (11)	N10—C9—H9	123.9
N4—C5—C6	120.23 (12)	N8—C9—H9	123.9
N4—C5—H5	119.9	C9—N10—C6	104.47 (11)
C6—C5—H5	119.9	H21A—O21—H21B	106 (2)
C7—C6—N10	109.59 (11)
N1—C2—N3—N4	3.30 (18)	C5—C6—C7—N8	−179.86 (12)
S1—C2—N3—N4	−177.56 (9)	C6—C7—N8—C9	−0.07 (15)
C2—N3—N4—C5	−175.73 (11)	C7—N8—C9—N10	−0.24 (16)
N3—N4—C5—C6	180.00 (11)	N8—C9—N10—C6	0.43 (15)
N4—C5—C6—C7	−175.90 (13)	C7—C6—N10—C9	−0.46 (15)
N4—C5—C6—N10	3.9 (2)	C5—C6—N10—C9	179.72 (12)
N10—C6—C7—N8	0.33 (15)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O21	0.92 (2)	2.34 (2)	3.2325 (16)	163.2 (18)
N8—H8···S1i	0.90 (2)	2.51 (2)	3.3334 (13)	153.0 (18)
O21—H21B···N10	0.87 (2)	2.17 (2)	3.0399 (15)	172 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O21	0.92 (2)	2.34 (2)	3.2325 (16)	163.2 (18)
N8—H8⋯S1i	0.90 (2)	2.51 (2)	3.3334 (13)	153.0 (18)
O21—H21B⋯N10	0.87 (2)	2.17 (2)	3.0399 (15)	172 (2)

Symmetry code: (i) .