(E)-1-(3-Eth-oxy-2-hy-droxy-benzyl-idene)thio-semicarbazide.

The title compound, C(10)H(13)N(3)O(2)S, crystallizes with two independent mol-ecules (A and B) in the asymmetric unit. In the crystal, the A and B mol-ecules are linked via pairs of N-H⋯O and O-H⋯S hydrogen bonds, forming dimers with R(2) (2)(14) and R(2) (2)(6) ring motifs. These dimers are linked via a pair of N-H⋯S hydrogen bonds with an R(2) (2)(8) ring motif, forming chains propagating along the c-axis direction. The crystal was refined as an inversion twin with a final BASF ratio of 0.54 (11):0.46 (11).

Related literature

For standard bond lengths, see: Allen et al. (1987 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For background to thio­semicarbazones in coordination chemistry, see: Casas et al. (2000 ▶). For their biological applications, see: for example, Maccioni et al. (2003 ▶); Ferrari et al. (2000 ▶). For related structures, see: Kargar et al. (2010 ▶).

Experimental

Crystal data

C10H13N3O2S

M = 239.29

Monoclinic,

a = 6.0728 (3) Å

b = 16.1595 (8) Å

c = 12.8490 (6) Å

β = 90.238 (3)°

V = 1260.91 (11) Å3

Z = 4

Mo Kα radiation

μ = 0.25 mm−1

T = 291 K

0.24 × 0.14 × 0.08 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.800, T max = 0.926

12062 measured reflections

5428 independent reflections

2303 reflections with I > 2σ(I)

R int = 0.075

Refinement

R[F 2 > 2σ(F 2)] = 0.056

wR(F 2) = 0.119

S = 0.92

5428 reflections

293 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.21 e Å−3

Δρmin = −0.21 e Å−3

Absolute structure: Flack (1983 ▶), 2232 Friedel pairs

Flack parameter: 0.54 (11)

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); 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 and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812000487/su2360sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812000487/su2360Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812000487/su2360Isup3.cml

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

C10H13N3O2S	F(000) = 504
Mr = 239.29	Dx = 1.261 Mg m−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 2525 reflections
a = 6.0728 (3) Å	θ = 2.5–29.5°
b = 16.1595 (8) Å	µ = 0.25 mm−1
c = 12.8490 (6) Å	T = 291 K
β = 90.238 (3)°	Plate, colourless
V = 1260.91 (11) Å3	0.24 × 0.14 × 0.08 mm
Z = 4

Bruker SMART APEX CCD area-detector diffractometer	5428 independent reflections
Radiation source: fine-focus sealed tube	2303 reflections with I > 2σ(I)
graphite	Rint = 0.075
φ and ω scans	θmax = 28.3°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −8→7
Tmin = 0.800, Tmax = 0.926	k = −21→19
12062 measured reflections	l = −17→17

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.056	w = 1/[σ2(Fo2) + (0.0341P)2] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.119	(Δ/σ)max < 0.001
S = 0.92	Δρmax = 0.21 e Å−3
5428 reflections	Δρmin = −0.21 e Å−3
293 parameters	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
1 restraint	Extinction coefficient: 0.0087 (9)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983), 2232 Friedel pairs
Secondary atom site location: difference Fourier map	Flack parameter: 0.54 (11)

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
C1	0.2843 (8)	0.3987 (3)	1.0328 (4)	0.0372 (13)
C2	0.1042 (9)	0.3625 (4)	1.0844 (4)	0.0424 (15)
C3	−0.0613 (8)	0.3257 (4)	1.0275 (4)	0.0485 (16)
H3	−0.1804	0.3020	1.0617	0.058*
C4	−0.0523 (9)	0.3236 (4)	0.9203 (4)	0.0562 (16)
H4	−0.1637	0.2980	0.8824	0.067*
C5	0.1241 (9)	0.3600 (3)	0.8695 (4)	0.0478 (15)
H5	0.1287	0.3594	0.7972	0.057*
C6	0.2951 (8)	0.3976 (3)	0.9255 (4)	0.0381 (13)
C7	−0.0470 (9)	0.3298 (4)	1.2529 (4)	0.062 (2)
H7A	−0.0526	0.2708	1.2390	0.074*
H7B	−0.1900	0.3534	1.2367	0.074*
C8	0.0081 (10)	0.3445 (4)	1.3637 (4)	0.079 (2)
H8A	0.1469	0.3190	1.3798	0.118*
H8B	−0.1046	0.3211	1.4069	0.118*
H8C	0.0177	0.4029	1.3763	0.118*
C9	0.4833 (8)	0.4345 (3)	0.8726 (4)	0.0420 (14)
H9	0.5945	0.4587	0.9121	0.050*
C10	0.7230 (8)	0.4779 (3)	0.6336 (4)	0.0528 (17)
N1	0.4996 (7)	0.4345 (3)	0.7738 (3)	0.0486 (13)
N2	0.6925 (7)	0.4696 (3)	0.7372 (3)	0.0530 (14)
H2N	0.7890	0.4848	0.7866	0.064*
N3	0.5579 (7)	0.4547 (3)	0.5733 (3)	0.0652 (15)
H3NA	0.4296	0.4346	0.5911	0.078*
H3NB	0.5698	0.4611	0.5043	0.078*
O1	0.4483 (5)	0.4339 (2)	1.0882 (2)	0.0512 (12)
H1O	0.4206	0.4284	1.1511	0.077*
O2	0.1182 (6)	0.3677 (2)	1.1904 (3)	0.0550 (10)
S1	0.9596 (2)	0.51784 (12)	0.58949 (9)	0.0666 (5)
C11	0.2184 (8)	0.6114 (3)	0.8747 (4)	0.0383 (13)
C12	0.3909 (9)	0.6490 (4)	0.8233 (4)	0.0451 (15)
C13	0.5576 (9)	0.6839 (4)	0.8776 (5)	0.0503 (17)
H13	0.6739	0.7091	0.8430	0.060*
C14	0.5540 (9)	0.6818 (3)	0.9861 (5)	0.0528 (17)
H14	0.6696	0.7051	1.0236	0.063*
C15	0.3844 (9)	0.6461 (4)	1.0377 (4)	0.0427 (15)
H15	0.3829	0.6460	1.1101	0.051*
C16	0.2128 (8)	0.6097 (3)	0.9825 (4)	0.0353 (13)
C17	0.5280 (10)	0.6936 (4)	0.6567 (4)	0.071 (2)
H17A	0.6758	0.6724	0.6673	0.086*
H17B	0.5247	0.7512	0.6779	0.086*
C18	0.4616 (12)	0.6855 (4)	0.5436 (4)	0.102 (3)
H18A	0.4782	0.6290	0.5219	0.152*
H18B	0.5537	0.7203	0.5018	0.152*
H18C	0.3106	0.7020	0.5353	0.152*
C19	−0.2344 (8)	0.5427 (3)	1.2735 (4)	0.0509 (16)
C20	0.0220 (8)	0.5732 (3)	1.0337 (4)	0.0389 (15)
H20	−0.0841	0.5461	0.9940	0.047*
N4	−0.0013 (6)	0.5781 (3)	1.1322 (3)	0.0391 (11)
N5	−0.1924 (6)	0.5445 (3)	1.1704 (3)	0.0479 (13)
H5N	−0.2845	0.5167	1.1315	0.058*
N6	−0.0761 (8)	0.5723 (3)	1.3345 (3)	0.0693 (16)
H6NA	0.0549	0.5759	1.3077	0.083*
H6NB	−0.0989	0.5638	1.4014	0.083*
O3	0.0473 (5)	0.5768 (2)	0.8190 (2)	0.0515 (11)
H3O	0.0650	0.5791	0.7552	0.077*
O4	0.3715 (6)	0.6459 (2)	0.7167 (3)	0.0589 (11)
S2	−0.4755 (2)	0.50462 (12)	1.31643 (9)	0.0625 (5)

	U11	U22	U33	U12	U13	U23
C1	0.034 (3)	0.040 (4)	0.038 (3)	−0.002 (3)	0.004 (3)	0.000 (3)
C2	0.040 (3)	0.048 (4)	0.039 (3)	0.001 (3)	0.009 (3)	0.005 (3)
C3	0.036 (3)	0.050 (4)	0.059 (4)	−0.006 (3)	0.012 (3)	0.001 (3)
C4	0.046 (4)	0.059 (5)	0.064 (4)	−0.011 (3)	−0.003 (3)	0.001 (3)
C5	0.054 (4)	0.044 (4)	0.045 (3)	−0.003 (3)	−0.003 (3)	0.004 (3)
C6	0.037 (3)	0.041 (4)	0.037 (3)	0.002 (3)	−0.002 (2)	0.000 (3)
C7	0.061 (4)	0.057 (5)	0.068 (5)	−0.002 (3)	0.032 (3)	0.020 (4)
C8	0.090 (5)	0.096 (7)	0.051 (4)	−0.002 (4)	0.028 (4)	0.014 (4)
C9	0.038 (3)	0.049 (4)	0.040 (3)	−0.002 (3)	−0.001 (2)	0.000 (3)
C10	0.047 (3)	0.077 (5)	0.035 (3)	−0.010 (3)	0.002 (3)	−0.005 (3)
N1	0.048 (3)	0.069 (4)	0.029 (3)	−0.006 (3)	0.007 (2)	0.003 (3)
N2	0.048 (3)	0.084 (4)	0.027 (2)	−0.011 (3)	0.001 (2)	0.002 (2)
N3	0.062 (3)	0.105 (5)	0.029 (3)	−0.030 (3)	0.000 (2)	0.002 (3)
O1	0.049 (2)	0.077 (3)	0.027 (2)	−0.016 (2)	0.0058 (18)	−0.005 (2)
O2	0.060 (3)	0.068 (3)	0.037 (2)	−0.010 (2)	0.0164 (19)	0.004 (2)
S1	0.0488 (9)	0.1187 (16)	0.0325 (8)	−0.0175 (10)	0.0068 (7)	0.0012 (10)
C11	0.038 (3)	0.039 (4)	0.038 (3)	−0.001 (3)	0.004 (3)	−0.008 (3)
C12	0.043 (3)	0.053 (4)	0.039 (3)	−0.007 (3)	0.014 (3)	−0.001 (3)
C13	0.037 (4)	0.054 (4)	0.060 (4)	−0.005 (3)	0.015 (3)	0.009 (3)
C14	0.043 (3)	0.047 (4)	0.068 (4)	−0.008 (3)	0.007 (3)	0.001 (3)
C15	0.045 (4)	0.041 (4)	0.042 (3)	0.003 (3)	−0.007 (3)	−0.005 (3)
C16	0.034 (3)	0.034 (4)	0.037 (3)	0.002 (3)	0.003 (2)	0.001 (3)
C17	0.081 (4)	0.077 (5)	0.056 (4)	−0.013 (4)	0.038 (4)	0.009 (4)
C18	0.131 (6)	0.123 (7)	0.050 (4)	0.001 (5)	0.039 (4)	0.008 (4)
C19	0.048 (3)	0.072 (5)	0.032 (3)	0.000 (3)	0.002 (3)	0.003 (3)
C20	0.038 (3)	0.050 (4)	0.030 (3)	0.006 (3)	−0.002 (2)	−0.002 (3)
N4	0.032 (2)	0.051 (3)	0.034 (3)	−0.006 (2)	−0.0008 (19)	0.005 (2)
N5	0.041 (3)	0.072 (4)	0.031 (2)	−0.010 (2)	−0.0018 (19)	0.000 (2)
N6	0.063 (3)	0.113 (5)	0.032 (3)	−0.025 (3)	−0.003 (3)	−0.004 (3)
O3	0.051 (2)	0.070 (3)	0.034 (2)	−0.017 (2)	0.0040 (18)	−0.0036 (19)
O4	0.063 (3)	0.067 (3)	0.047 (2)	−0.013 (2)	0.019 (2)	0.001 (2)
S2	0.0463 (9)	0.1101 (15)	0.0313 (8)	−0.0101 (10)	0.0066 (6)	0.0014 (9)

C1—O1	1.347 (5)	C11—O3	1.378 (5)
C1—C6	1.381 (6)	C11—C12	1.382 (6)
C1—C2	1.409 (6)	C11—C16	1.385 (6)
C2—O2	1.367 (6)	C12—C13	1.351 (7)
C2—C3	1.375 (7)	C12—O4	1.375 (6)
C3—C4	1.379 (7)	C13—C14	1.395 (8)
C3—H3	0.9300	C13—H13	0.9300
C4—C5	1.387 (6)	C14—C15	1.356 (6)
C4—H4	0.9300	C14—H14	0.9300
C5—C6	1.399 (6)	C15—C16	1.389 (7)
C5—H5	0.9300	C15—H15	0.9300
C6—C9	1.460 (6)	C16—C20	1.459 (6)
C7—O2	1.426 (5)	C17—O4	1.447 (5)
C7—C8	1.480 (8)	C17—C18	1.513 (8)
C7—H7A	0.9700	C17—H17A	0.9700
C7—H7B	0.9700	C17—H17B	0.9700
C8—H8A	0.9600	C18—H18A	0.9600
C8—H8B	0.9600	C18—H18B	0.9600
C8—H8C	0.9600	C18—H18C	0.9600
C9—N1	1.273 (6)	C19—N6	1.327 (6)
C9—H9	0.9300	C19—N5	1.350 (5)
C10—N3	1.319 (6)	C19—S2	1.684 (5)
C10—N2	1.351 (5)	C20—N4	1.277 (6)
C10—S1	1.676 (5)	C20—H20	0.9300
N1—N2	1.386 (5)	N4—N5	1.374 (5)
N2—H2N	0.8964	N5—H5N	0.8736
N3—H3NA	0.8753	N6—H6NA	0.8703
N3—H3NB	0.8958	N6—H6NB	0.8816
O1—H1O	0.8316	O3—H3O	0.8286
O1—C1—C6	119.7 (4)	O3—C11—C12	120.1 (5)
O1—C1—C2	120.0 (5)	O3—C11—C16	119.3 (4)
C6—C1—C2	120.3 (5)	C12—C11—C16	120.6 (5)
O2—C2—C3	126.7 (5)	C13—C12—O4	126.2 (5)
O2—C2—C1	113.5 (5)	C13—C12—C11	120.3 (5)
C3—C2—C1	119.8 (5)	O4—C12—C11	113.5 (5)
C2—C3—C4	120.6 (5)	C12—C13—C14	119.5 (5)
C2—C3—H3	119.7	C12—C13—H13	120.3
C4—C3—H3	119.7	C14—C13—H13	120.3
C3—C4—C5	119.6 (5)	C15—C14—C13	120.9 (5)
C3—C4—H4	120.2	C15—C14—H14	119.5
C5—C4—H4	120.2	C13—C14—H14	119.5
C4—C5—C6	121.0 (5)	C14—C15—C16	120.0 (5)
C4—C5—H5	119.5	C14—C15—H15	120.0
C6—C5—H5	119.5	C16—C15—H15	120.0
C1—C6—C5	118.7 (5)	C11—C16—C15	118.7 (5)
C1—C6—C9	120.0 (5)	C11—C16—C20	118.8 (5)
C5—C6—C9	121.3 (5)	C15—C16—C20	122.4 (5)
O2—C7—C8	108.4 (5)	O4—C17—C18	107.0 (5)
O2—C7—H7A	110.0	O4—C17—H17A	110.3
C8—C7—H7A	110.0	C18—C17—H17A	110.3
O2—C7—H7B	110.0	O4—C17—H17B	110.3
C8—C7—H7B	110.0	C18—C17—H17B	110.3
H7A—C7—H7B	108.4	H17A—C17—H17B	108.6
C7—C8—H8A	109.5	C17—C18—H18A	109.5
C7—C8—H8B	109.5	C17—C18—H18B	109.5
H8A—C8—H8B	109.5	H18A—C18—H18B	109.5
C7—C8—H8C	109.5	C17—C18—H18C	109.5
H8A—C8—H8C	109.5	H18A—C18—H18C	109.5
H8B—C8—H8C	109.5	H18B—C18—H18C	109.5
N1—C9—C6	121.9 (5)	N6—C19—N5	115.6 (4)
N1—C9—H9	119.0	N6—C19—S2	124.6 (4)
C6—C9—H9	119.0	N5—C19—S2	119.8 (4)
N3—C10—N2	116.4 (4)	N4—C20—C16	120.9 (5)
N3—C10—S1	124.1 (4)	N4—C20—H20	119.5
N2—C10—S1	119.5 (4)	C16—C20—H20	119.5
C9—N1—N2	114.1 (5)	C20—N4—N5	115.3 (4)
C10—N2—N1	119.6 (4)	C19—N5—N4	121.5 (4)
C10—N2—H2N	125.4	C19—N5—H5N	115.4
N1—N2—H2N	115.0	N4—N5—H5N	122.6
C10—N3—H3NA	128.8	C19—N6—H6NA	116.8
C10—N3—H3NB	119.0	C19—N6—H6NB	113.8
H3NA—N3—H3NB	112.1	H6NA—N6—H6NB	122.9
C1—O1—H1O	108.4	C11—O3—H3O	113.3
C2—O2—C7	119.6 (4)	C12—O4—C17	117.2 (4)
O1—C1—C2—O2	0.0 (7)	O3—C11—C12—C13	179.2 (5)
C6—C1—C2—O2	179.3 (5)	C16—C11—C12—C13	0.7 (8)
O1—C1—C2—C3	−179.1 (5)	O3—C11—C12—O4	−1.1 (7)
C6—C1—C2—C3	0.1 (8)	C16—C11—C12—O4	−179.6 (4)
O2—C2—C3—C4	−178.7 (5)	O4—C12—C13—C14	−179.8 (5)
C1—C2—C3—C4	0.3 (8)	C11—C12—C13—C14	−0.1 (8)
C2—C3—C4—C5	−0.9 (8)	C12—C13—C14—C15	−0.8 (8)
C3—C4—C5—C6	1.1 (8)	C13—C14—C15—C16	1.2 (8)
O1—C1—C6—C5	179.3 (4)	O3—C11—C16—C15	−178.9 (5)
C2—C1—C6—C5	0.1 (7)	C12—C11—C16—C15	−0.3 (7)
O1—C1—C6—C9	−0.1 (7)	O3—C11—C16—C20	−1.7 (7)
C2—C1—C6—C9	−179.4 (5)	C12—C11—C16—C20	176.8 (5)
C4—C5—C6—C1	−0.7 (8)	C14—C15—C16—C11	−0.6 (8)
C4—C5—C6—C9	178.7 (5)	C14—C15—C16—C20	−177.6 (5)
C1—C6—C9—N1	179.8 (5)	C11—C16—C20—N4	−172.5 (5)
C5—C6—C9—N1	0.4 (8)	C15—C16—C20—N4	4.5 (8)
C6—C9—N1—N2	−177.9 (4)	C16—C20—N4—N5	177.3 (4)
N3—C10—N2—N1	2.9 (8)	N6—C19—N5—N4	−2.6 (8)
S1—C10—N2—N1	−178.2 (4)	S2—C19—N5—N4	177.4 (4)
C9—N1—N2—C10	−175.9 (5)	C20—N4—N5—C19	177.6 (5)
C3—C2—O2—C7	2.3 (8)	C13—C12—O4—C17	−8.7 (8)
C1—C2—O2—C7	−176.8 (5)	C11—C12—O4—C17	171.6 (5)
C8—C7—O2—C2	179.8 (5)	C18—C17—O4—C12	−175.6 (5)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O···S2i	0.83	2.53	3.180 (4)	135
O3—H3O···S1ii	0.83	2.43	3.143 (4)	145
N2—H2N···O3i	0.90	2.20	2.954 (6)	142
N5—H5N···O1ii	0.87	2.17	3.009 (5)	160
N3—H3NB···S2iii	0.90	2.53	3.403 (4)	166
N6—H6NB···S1iv	0.88	2.55	3.398 (5)	161

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1O⋯S2i	0.83	2.53	3.180 (4)	135
O3—H3O⋯S1ii	0.83	2.43	3.143 (4)	145
N2—H2N⋯O3i	0.90	2.20	2.954 (6)	142
N5—H5N⋯O1ii	0.87	2.17	3.009 (5)	160
N3—H3NB⋯S2iii	0.90	2.53	3.403 (4)	166
N6—H6NB⋯S1iv	0.88	2.55	3.398 (5)	161

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