1,5-Bis[(E)-1-(2-hydroxyphenyl)ethyl-idene]thiocarbonohydrazide mono-hydrate.

In the title compound, C(17)H(18)N(4)O(2)S·H(2)O, the thio-urea derivative is almost planar, with an r.m.s. deviation for the non-H atoms of 0.057 Å. The hydroxyl groups lie to the same side of the mol-ecule as the thione S atom, a conformation that allows the formation of intra-molecular O-H⋯S and O-H⋯N hydrogen bonds. In the crystal structure, the thio-urea and water mol-ecules self-assemble into a two-dimensional array by a combination of O(water)-H⋯O(hydrox-yl), N-H⋯O(water) and O(water)-H⋯S hydrogen bonds and C-H⋯π inter-actions.

Related literature

For background and recent studies of the biological activity of organotin compounds, see: Gielen & Tiekink (2005 ▶); Affan et al. (2009 ▶). For the structure of the ketone analogue of the title compound, see: Zukerman-Schpector et al. (2009 ▶).

Experimental

Crystal data

C17H18N4O2S·n class="Chemical">H2O

M = 360.43

Monoclinic,

a = 15.8654 (3) Å

b = 7.3938 (1) Å

c = 16.3697 (3) Å

β = 115.922 (1)°

V = 1727.06 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.21 mm−1

T = 100 K

0.44 × 0.13 × 0.07 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.905, T max = 1

15464 measured reflections

3968 independent reflections

3136 reflections with I > 2σ(I)

R int = 0.033

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.102

S = 1.03

3968 reflections

246 parameters

7 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.35 e Å−3

Δρmin = −0.27 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS86 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810004241/hb5327sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810004241/hb5327Isup2.hkl

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

C17H18N4O2S·H2O	F(000) = 760
Mr = 360.43	Dx = 1.386 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 4324 reflections
a = 15.8654 (3) Å	θ = 2.9–27.4°
b = 7.3938 (1) Å	µ = 0.21 mm−1
c = 16.3697 (3) Å	T = 100 K
β = 115.922 (1)°	Prism, colourless
V = 1727.06 (5) Å3	0.44 × 0.13 × 0.07 mm
Z = 4

Bruker SMART APEXII CCD diffractometer	3968 independent reflections
Radiation source: sealed tube	3136 reflections with I > 2σ(I)
graphite	Rint = 0.033
φ and ω scans	θmax = 27.5°, θmin = 1.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −20→20
Tmin = 0.905, Tmax = 1	k = −9→8
15464 measured reflections	l = −21→21

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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.102	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ2(Fo2) + (0.0487P)2 + 0.7503P] where P = (Fo2 + 2Fc2)/3
3968 reflections	(Δ/σ)max = 0.001
246 parameters	Δρmax = 0.35 e Å−3
7 restraints	Δρmin = −0.27 e Å−3

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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	0.65089 (3)	0.17338 (6)	0.56929 (3)	0.02002 (12)
O1	0.65341 (7)	0.31213 (16)	0.77557 (8)	0.0213 (3)
H1O	0.6224 (14)	0.300 (3)	0.7201 (15)	0.032*
O2	0.70052 (8)	−0.01110 (17)	0.38996 (7)	0.0225 (3)
H2O	0.6629 (14)	0.041 (3)	0.4040 (14)	0.034*
O3	0.82009 (8)	0.13214 (18)	0.86971 (9)	0.0240 (3)
H3O	0.7673 (15)	0.180 (3)	0.8392 (15)	0.036*
H4O	0.8143 (14)	0.022 (3)	0.8646 (15)	0.036*
N1	0.47863 (9)	0.29267 (19)	0.53363 (9)	0.0179 (3)
H1N	0.4205 (13)	0.313 (2)	0.4972 (12)	0.022*
N2	0.51214 (9)	0.33207 (18)	0.62387 (8)	0.0166 (3)
N3	0.49527 (9)	0.19563 (19)	0.41174 (9)	0.0179 (3)
H3N	0.4365 (13)	0.229 (3)	0.3827 (13)	0.021*
N4	0.54462 (9)	0.12100 (18)	0.36967 (9)	0.0172 (3)
C1	0.53819 (10)	0.2217 (2)	0.50290 (11)	0.0170 (3)
C2	0.45776 (10)	0.4008 (2)	0.65560 (10)	0.0158 (3)
C3	0.35589 (10)	0.4419 (2)	0.59818 (11)	0.0203 (3)
H3A	0.3499	0.5603	0.5693	0.030*
H3B	0.3227	0.4433	0.6365	0.030*
H3C	0.3287	0.3488	0.5513	0.030*
C4	0.50342 (10)	0.4407 (2)	0.75353 (10)	0.0163 (3)
C5	0.59838 (11)	0.3942 (2)	0.80910 (11)	0.0175 (3)
C6	0.63916 (11)	0.4332 (2)	0.90125 (11)	0.0206 (3)
H6	0.7024	0.3997	0.9379	0.025*
C7	0.58878 (11)	0.5202 (2)	0.94020 (11)	0.0225 (4)
H7	0.6175	0.5468	1.0033	0.027*
C8	0.49609 (11)	0.5689 (2)	0.88708 (11)	0.0223 (4)
H8	0.4613	0.6295	0.9136	0.027*
C9	0.45484 (11)	0.5287 (2)	0.79543 (11)	0.0191 (3)
H9	0.3913	0.5619	0.7598	0.023*
C10	0.50214 (11)	0.0843 (2)	0.28371 (10)	0.0172 (3)
C11	0.39945 (11)	0.1186 (2)	0.22693 (11)	0.0235 (4)
H11A	0.3647	0.0869	0.2618	0.035*
H11B	0.3771	0.0445	0.1718	0.035*
H11C	0.3896	0.2468	0.2101	0.035*
C12	0.56124 (11)	0.0036 (2)	0.24484 (10)	0.0178 (3)
C13	0.65610 (11)	−0.0429 (2)	0.29941 (11)	0.0187 (3)
C14	0.70852 (11)	−0.1286 (2)	0.26121 (11)	0.0227 (4)
H14	0.7713	−0.1634	0.2990	0.027*
C15	0.67062 (12)	−0.1635 (2)	0.16938 (12)	0.0242 (4)
H15	0.7073	−0.2212	0.1440	0.029*
C16	0.57851 (12)	−0.1140 (2)	0.11390 (11)	0.0247 (4)
H16	0.5523	−0.1360	0.0504	0.030*
C17	0.52543 (12)	−0.0331 (2)	0.15140 (11)	0.0217 (4)
H17	0.4624	−0.0010	0.1128	0.026*

	U11	U22	U33	U12	U13	U23
S1	0.01439 (18)	0.0259 (2)	0.01724 (19)	0.00368 (15)	0.00456 (14)	0.00086 (17)
O1	0.0168 (5)	0.0242 (6)	0.0187 (6)	0.0036 (5)	0.0039 (5)	−0.0026 (5)
O2	0.0162 (5)	0.0326 (7)	0.0167 (6)	0.0010 (5)	0.0054 (5)	−0.0034 (5)
O3	0.0144 (5)	0.0226 (7)	0.0283 (6)	0.0009 (5)	0.0031 (5)	−0.0023 (6)
N1	0.0135 (6)	0.0230 (8)	0.0150 (6)	0.0015 (5)	0.0042 (5)	−0.0006 (6)
N2	0.0165 (6)	0.0166 (7)	0.0148 (6)	−0.0005 (5)	0.0049 (5)	0.0007 (5)
N3	0.0142 (6)	0.0210 (7)	0.0162 (6)	0.0020 (5)	0.0046 (5)	−0.0002 (6)
N4	0.0170 (6)	0.0167 (7)	0.0176 (6)	−0.0003 (5)	0.0075 (5)	0.0003 (5)
C1	0.0168 (7)	0.0155 (8)	0.0180 (8)	−0.0017 (6)	0.0069 (6)	0.0014 (6)
C2	0.0152 (7)	0.0135 (8)	0.0181 (7)	−0.0021 (6)	0.0066 (6)	0.0014 (6)
C3	0.0165 (7)	0.0247 (9)	0.0182 (8)	−0.0006 (6)	0.0062 (6)	−0.0005 (7)
C4	0.0162 (7)	0.0139 (8)	0.0179 (7)	−0.0031 (6)	0.0066 (6)	0.0008 (6)
C5	0.0175 (7)	0.0130 (8)	0.0212 (8)	−0.0013 (6)	0.0078 (6)	0.0005 (6)
C6	0.0179 (7)	0.0185 (9)	0.0200 (8)	−0.0027 (6)	0.0032 (6)	0.0014 (7)
C7	0.0253 (8)	0.0226 (9)	0.0177 (8)	−0.0057 (7)	0.0075 (7)	−0.0023 (7)
C8	0.0247 (8)	0.0211 (9)	0.0243 (8)	−0.0022 (7)	0.0136 (7)	−0.0031 (7)
C9	0.0167 (7)	0.0194 (8)	0.0209 (8)	−0.0015 (6)	0.0081 (6)	0.0008 (7)
C10	0.0186 (7)	0.0132 (8)	0.0176 (7)	−0.0033 (6)	0.0058 (6)	0.0015 (6)
C11	0.0193 (8)	0.0236 (9)	0.0226 (8)	−0.0014 (6)	0.0046 (7)	0.0001 (7)
C12	0.0212 (8)	0.0136 (8)	0.0170 (7)	−0.0025 (6)	0.0069 (6)	0.0014 (6)
C13	0.0206 (7)	0.0181 (8)	0.0172 (7)	−0.0049 (6)	0.0080 (6)	0.0006 (6)
C14	0.0190 (8)	0.0249 (9)	0.0243 (8)	−0.0027 (6)	0.0096 (7)	0.0006 (7)
C15	0.0319 (9)	0.0202 (9)	0.0263 (9)	−0.0032 (7)	0.0181 (7)	−0.0024 (7)
C16	0.0360 (9)	0.0202 (9)	0.0169 (8)	−0.0018 (7)	0.0105 (7)	−0.0019 (7)
C17	0.0248 (8)	0.0168 (8)	0.0186 (8)	0.0003 (6)	0.0050 (7)	0.0008 (7)

S1—C1	1.6754 (15)	C6—C7	1.380 (2)
O1—C5	1.3606 (19)	C6—H6	0.9500
O1—H1O	0.83 (2)	C7—C8	1.389 (2)
O2—C13	1.3550 (19)	C7—H7	0.9500
O2—H2O	0.82 (2)	C8—C9	1.382 (2)
O3—H3O	0.84 (2)	C8—H8	0.9500
O3—H4O	0.82 (2)	C9—H9	0.9500
N1—C1	1.355 (2)	C10—C12	1.470 (2)
N1—N2	1.3649 (18)	C10—C11	1.503 (2)
N1—H1N	0.865 (18)	C11—H11A	0.9800
N2—C2	1.290 (2)	C11—H11B	0.9800
N3—C1	1.356 (2)	C11—H11C	0.9800
N3—N4	1.3650 (18)	C12—C17	1.406 (2)
N3—H3N	0.876 (18)	C12—C13	1.416 (2)
N4—C10	1.2956 (19)	C13—C14	1.392 (2)
C2—C4	1.472 (2)	C14—C15	1.378 (2)
C2—C3	1.503 (2)	C14—H14	0.9500
C3—H3A	0.9800	C15—C16	1.391 (2)
C3—H3B	0.9800	C15—H15	0.9500
C3—H3C	0.9800	C16—C17	1.377 (2)
C4—C9	1.396 (2)	C16—H16	0.9500
C4—C5	1.420 (2)	C17—H17	0.9500
C5—C6	1.387 (2)
C5—O1—H1O	108.2 (14)	C8—C7—H7	120.0
C13—O2—H2O	107.0 (14)	C9—C8—C7	119.54 (16)
H3O—O3—H4O	109 (2)	C9—C8—H8	120.2
C1—N1—N2	118.65 (13)	C7—C8—H8	120.2
C1—N1—H1N	121.2 (12)	C8—C9—C4	122.18 (14)
N2—N1—H1N	120.2 (12)	C8—C9—H9	118.9
C2—N2—N1	120.48 (12)	C4—C9—H9	118.9
C1—N3—N4	119.32 (13)	N4—C10—C12	115.31 (13)
C1—N3—H3N	117.4 (12)	N4—C10—C11	123.03 (15)
N4—N3—H3N	123.3 (12)	C12—C10—C11	121.65 (14)
C10—N4—N3	119.45 (13)	C10—C11—H11A	109.5
N1—C1—N3	111.55 (13)	C10—C11—H11B	109.5
N1—C1—S1	124.15 (12)	H11A—C11—H11B	109.5
N3—C1—S1	124.30 (12)	C10—C11—H11C	109.5
N2—C2—C4	114.84 (13)	H11A—C11—H11C	109.5
N2—C2—C3	123.59 (14)	H11B—C11—H11C	109.5
C4—C2—C3	121.55 (14)	C17—C12—C13	116.86 (15)
C2—C3—H3A	109.5	C17—C12—C10	121.22 (14)
C2—C3—H3B	109.5	C13—C12—C10	121.91 (14)
H3A—C3—H3B	109.5	O2—C13—C14	116.31 (14)
C2—C3—H3C	109.5	O2—C13—C12	123.28 (15)
H3A—C3—H3C	109.5	C14—C13—C12	120.40 (15)
H3B—C3—H3C	109.5	C15—C14—C13	120.93 (15)
C9—C4—C5	117.19 (14)	C15—C14—H14	119.5
C9—C4—C2	120.92 (13)	C13—C14—H14	119.5
C5—C4—C2	121.88 (14)	C14—C15—C16	119.74 (16)
O1—C5—C6	117.06 (14)	C14—C15—H15	120.1
O1—C5—C4	122.53 (14)	C16—C15—H15	120.1
C6—C5—C4	120.40 (15)	C17—C16—C15	119.75 (15)
C7—C6—C5	120.68 (15)	C17—C16—H16	120.1
C7—C6—H6	119.7	C15—C16—H16	120.1
C5—C6—H6	119.7	C16—C17—C12	122.27 (15)
C6—C7—C8	120.00 (15)	C16—C17—H17	118.9
C6—C7—H7	120.0	C12—C17—H17	118.9
C1—N1—N2—C2	179.58 (14)	C7—C8—C9—C4	−0.4 (3)
C1—N3—N4—C10	175.22 (15)	C5—C4—C9—C8	−0.4 (2)
N2—N1—C1—N3	−178.03 (13)	C2—C4—C9—C8	−179.56 (15)
N2—N1—C1—S1	1.7 (2)	N3—N4—C10—C12	−179.77 (13)
N4—N3—C1—N1	−178.53 (13)	N3—N4—C10—C11	−0.5 (2)
N4—N3—C1—S1	1.8 (2)	N4—C10—C12—C17	−176.26 (15)
N1—N2—C2—C4	−178.58 (13)	C11—C10—C12—C17	4.5 (2)
N1—N2—C2—C3	0.2 (2)	N4—C10—C12—C13	4.6 (2)
N2—C2—C4—C9	174.83 (15)	C11—C10—C12—C13	−174.62 (15)
C3—C2—C4—C9	−4.0 (2)	C17—C12—C13—O2	178.25 (15)
N2—C2—C4—C5	−4.3 (2)	C10—C12—C13—O2	−2.6 (2)
C3—C2—C4—C5	176.85 (15)	C17—C12—C13—C14	−2.9 (2)
C9—C4—C5—O1	−178.43 (14)	C10—C12—C13—C14	176.31 (15)
C2—C4—C5—O1	0.8 (2)	O2—C13—C14—C15	−178.53 (15)
C9—C4—C5—C6	1.0 (2)	C12—C13—C14—C15	2.5 (3)
C2—C4—C5—C6	−179.76 (15)	C13—C14—C15—C16	−0.5 (3)
O1—C5—C6—C7	178.47 (15)	C14—C15—C16—C17	−1.0 (3)
C4—C5—C6—C7	−1.0 (2)	C15—C16—C17—C12	0.6 (3)
C5—C6—C7—C8	0.3 (3)	C13—C12—C17—C16	1.4 (2)
C6—C7—C8—C9	0.4 (3)	C10—C12—C17—C16	−177.81 (15)

Cg1 is the centroid of the C4–C9 ring.

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O···N2	0.83 (2)	1.79 (2)	2.5191 (17)	147 (2)
O1—H1O···S1	0.83 (2)	2.86 (2)	3.5126 (13)	138 (2)
O2—H2O···N4	0.82 (2)	1.81 (2)	2.542 (2)	148 (2)
O2—H2O···S1	0.82 (2)	2.96 (2)	3.6220 (15)	139 (2)
O3—H3O···O1	0.84 (2)	1.91 (2)	2.7525 (18)	174 (2)
O3—H4O···S1i	0.82 (2)	2.76 (2)	3.5089 (14)	154 (2)
N1—H1N···O3ii	0.87 (2)	2.04 (2)	2.8169 (19)	150 (2)
N3—H3N···O3ii	0.88 (2)	2.04 (2)	2.854 (2)	154 (2)
C11—H11C···Cg1iii	0.98	2.61	3.4497 (17)	144

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C4–C9 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1O⋯N2	0.83 (2)	1.79 (2)	2.5191 (17)	147 (2)
O1—H1O⋯S1	0.83 (2)	2.86 (2)	3.5126 (13)	138 (2)
O2—H2O⋯N4	0.82 (2)	1.81 (2)	2.542 (2)	148 (2)
O2—H2O⋯S1	0.82 (2)	2.96 (2)	3.6220 (15)	139 (2)
O3—H3O⋯O1	0.84 (2)	1.91 (2)	2.7525 (18)	174 (2)
O3—H4O⋯S1i	0.82 (2)	2.76 (2)	3.5089 (14)	154 (2)
N1—H1N⋯O3ii	0.87 (2)	2.04 (2)	2.8169 (19)	150 (2)
N3—H3N⋯O3ii	0.88 (2)	2.04 (2)	2.854 (2)	154 (2)
C11—H11C⋯Cg1iii	0.98	2.61	3.4497 (17)	144

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