1-(2,3,4-Trihydroxy-benzyl-idene)-4-ethyl-thio-semicarbazide.

In the title mol-ecule, C(10)H(13)N(3)O(3)S, the thio-semicarbazide =N-NH-C(=S)-NH- fragment is twisted with respect to the aromatic ring [dihedral angle = 20.5 (1)°]. A weak N-H⋯S hydrogen bond [3.480 (1) Å] links two mol-ecules about a center of inversion to generate a ring. The hydr-oxy groups are engaged in inter-molecular hydrogen bonding; the O-H⋯O and O-H⋯S hydrogen bonds generate a layer motif.

Related literature

For the crystal structures of 3,4-dihydroxy­benzaldehyde 4-ethyl­thio­semicarbazone and 2,4-dihydroxy­benzaldehyde 4-ethyl­thio­semicarbazone, see: Kayed et al. (2008 ▶); Tan et al. (2008 ▶).

Experimental

Crystal data

C10H13N3O3S

M = 255.29

Monoclinic,

a = 7.5668 (5) Å

b = 14.6754 (10) Å

c = 10.8700 (7) Å

β = 104.711 (1)°

V = 1167.50 (13) Å3

Z = 4

Mo Kα radiation

μ = 0.28 mm−1

T = 100 K

0.30 × 0.20 × 0.10 mm

Data collection

Bruker SMART APEX diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.921, T max = 0.973

10870 measured reflections

2660 independent reflections

2364 reflections with I > 2σ(I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.029

wR(F 2) = 0.082

S = 1.04

2660 reflections

174 parameters

5 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.34 e Å−3

Δρmin = −0.22 e Å−3

Data collection: APEX2 software (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: X-SEED (Barbour, 2001 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810014078/pk2241sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810014078/pk2241Isup2.hkl

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

C10H13N3O3S	F(000) = 536
Mr = 255.29	Dx = 1.452 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5730 reflections
a = 7.5668 (5) Å	θ = 2.4–28.3°
b = 14.6754 (10) Å	µ = 0.28 mm−1
c = 10.8700 (7) Å	T = 100 K
β = 104.711 (1)°	Prism, colorless
V = 1167.50 (13) Å3	0.30 × 0.20 × 0.10 mm
Z = 4

Bruker SMART APEX diffractometer	2660 independent reflections
Radiation source: fine-focus sealed tube	2364 reflections with I > 2σ(I)
graphite	Rint = 0.026
ω scans	θmax = 27.5°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→9
Tmin = 0.921, Tmax = 0.973	k = −19→19
10870 measured reflections	l = −14→13

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)] = 0.029	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.082	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ2(Fo2) + (0.0437P)2 + 0.4981P] where P = (Fo2 + 2Fc2)/3
2660 reflections	(Δ/σ)max = 0.001
174 parameters	Δρmax = 0.34 e Å−3
5 restraints	Δρmin = −0.21 e Å−3

	x	y	z	Uiso*/Ueq
S1	0.70929 (4)	0.59538 (2)	0.58991 (3)	0.01292 (10)
O1	0.50792 (13)	0.28115 (6)	0.03429 (8)	0.0153 (2)
O2	0.54351 (14)	0.26317 (6)	−0.20701 (9)	0.0176 (2)
O3	0.73079 (14)	0.39064 (6)	−0.30899 (9)	0.0167 (2)
N1	0.73526 (15)	0.49383 (7)	0.26113 (10)	0.0133 (2)
N2	0.69204 (15)	0.50533 (7)	0.37631 (10)	0.0132 (2)
N3	0.91494 (16)	0.61386 (8)	0.42338 (11)	0.0150 (2)
C1	0.66760 (17)	0.42305 (8)	0.05845 (12)	0.0114 (2)
C2	0.59670 (17)	0.34728 (8)	−0.01603 (12)	0.0114 (2)
C3	0.61719 (17)	0.33861 (8)	−0.13940 (12)	0.0122 (2)
C4	0.71179 (18)	0.40505 (8)	−0.18813 (12)	0.0123 (2)
C5	0.78291 (17)	0.48082 (9)	−0.11516 (12)	0.0134 (3)
H5	0.8474	0.5261	−0.1486	0.016*
C6	0.75918 (17)	0.48975 (8)	0.00612 (12)	0.0127 (2)
H6	0.8059	0.5421	0.0550	0.015*
C7	0.64158 (17)	0.43394 (8)	0.18633 (12)	0.0124 (2)
H7	0.5559	0.3969	0.2138	0.015*
C8	0.77826 (17)	0.57177 (8)	0.45530 (12)	0.0118 (2)
C9	1.01416 (19)	0.69298 (9)	0.48851 (13)	0.0168 (3)
H9A	1.1456	0.6869	0.4917	0.020*
H9B	1.0020	0.6951	0.5770	0.020*
C10	0.9416 (2)	0.78045 (10)	0.42107 (17)	0.0283 (4)
H10A	1.0080	0.8323	0.4678	0.042*
H10B	0.8112	0.7863	0.4171	0.042*
H10C	0.9584	0.7795	0.3346	0.042*
H1O	0.472 (3)	0.2409 (11)	−0.0195 (16)	0.039 (6)*
H2O	0.554 (3)	0.2673 (15)	−0.2817 (11)	0.045 (6)*
H3O	0.731 (3)	0.4420 (9)	−0.343 (2)	0.047 (6)*
H2N	0.5992 (17)	0.4785 (11)	0.3933 (15)	0.021 (4)*
H3N	0.936 (2)	0.5975 (11)	0.3531 (11)	0.023 (4)*

	U11	U22	U33	U12	U13	U23
S1	0.01775 (18)	0.01251 (16)	0.00958 (16)	−0.00113 (11)	0.00547 (12)	−0.00111 (10)
O1	0.0228 (5)	0.0130 (4)	0.0113 (4)	−0.0065 (4)	0.0064 (4)	−0.0022 (3)
O2	0.0281 (5)	0.0147 (5)	0.0114 (5)	−0.0064 (4)	0.0078 (4)	−0.0041 (4)
O3	0.0259 (5)	0.0153 (5)	0.0110 (5)	0.0000 (4)	0.0089 (4)	0.0007 (3)
N1	0.0157 (5)	0.0150 (5)	0.0104 (5)	−0.0001 (4)	0.0056 (4)	−0.0018 (4)
N2	0.0155 (5)	0.0149 (5)	0.0109 (5)	−0.0040 (4)	0.0063 (4)	−0.0028 (4)
N3	0.0185 (6)	0.0158 (5)	0.0126 (5)	−0.0046 (4)	0.0075 (4)	−0.0047 (4)
C1	0.0116 (6)	0.0122 (5)	0.0103 (6)	0.0016 (4)	0.0024 (4)	0.0003 (4)
C2	0.0118 (6)	0.0105 (5)	0.0124 (6)	0.0007 (4)	0.0038 (5)	0.0015 (4)
C3	0.0144 (6)	0.0109 (6)	0.0109 (6)	0.0011 (5)	0.0023 (5)	−0.0012 (4)
C4	0.0137 (6)	0.0144 (6)	0.0096 (6)	0.0034 (5)	0.0042 (5)	0.0009 (4)
C5	0.0132 (6)	0.0129 (6)	0.0144 (6)	−0.0004 (5)	0.0040 (5)	0.0027 (5)
C6	0.0127 (6)	0.0118 (6)	0.0126 (6)	−0.0003 (5)	0.0016 (5)	−0.0010 (5)
C7	0.0138 (6)	0.0111 (6)	0.0128 (6)	0.0005 (5)	0.0042 (5)	0.0002 (4)
C8	0.0140 (6)	0.0104 (5)	0.0110 (6)	0.0015 (5)	0.0028 (5)	0.0011 (4)
C9	0.0182 (7)	0.0164 (6)	0.0167 (6)	−0.0067 (5)	0.0060 (5)	−0.0043 (5)
C10	0.0201 (8)	0.0167 (7)	0.0444 (10)	−0.0032 (6)	0.0012 (7)	0.0005 (6)

S1—C8	1.7092 (13)	C1—C6	1.4007 (17)
O1—C2	1.3707 (15)	C1—C7	1.4613 (17)
O1—H1O	0.827 (9)	C2—C3	1.3944 (17)
O2—C3	1.3669 (15)	C3—C4	1.3914 (17)
O2—H2O	0.838 (9)	C4—C5	1.3923 (17)
O3—C4	1.3738 (15)	C5—C6	1.3811 (17)
O3—H3O	0.841 (9)	C5—H5	0.9500
N1—C7	1.2819 (16)	C6—H6	0.9500
N1—N2	1.3824 (14)	C7—H7	0.9500
N2—C8	1.3523 (16)	C9—C10	1.511 (2)
N2—H2N	0.866 (9)	C9—H9A	0.9900
N3—C8	1.3244 (17)	C9—H9B	0.9900
N3—C9	1.4639 (16)	C10—H10A	0.9800
N3—H3N	0.853 (9)	C10—H10B	0.9800
C1—C2	1.3996 (17)	C10—H10C	0.9800
C2—O1—H1O	109.3 (15)	C6—C5—H5	120.2
C3—O2—H2O	109.6 (15)	C4—C5—H5	120.2
C4—O3—H3O	107.5 (15)	C5—C6—C1	121.26 (11)
C7—N1—N2	115.99 (11)	C5—C6—H6	119.4
C8—N2—N1	118.43 (11)	C1—C6—H6	119.4
C8—N2—H2N	118.7 (11)	N1—C7—C1	119.47 (11)
N1—N2—H2N	122.0 (11)	N1—C7—H7	120.3
C8—N3—C9	125.59 (11)	C1—C7—H7	120.3
C8—N3—H3N	116.0 (12)	N3—C8—N2	116.93 (11)
C9—N3—H3N	117.8 (12)	N3—C8—S1	123.94 (10)
C2—C1—C6	118.47 (11)	N2—C8—S1	119.13 (10)
C2—C1—C7	120.84 (11)	N3—C9—C10	111.14 (11)
C6—C1—C7	120.66 (11)	N3—C9—H9A	109.4
O1—C2—C3	120.30 (11)	C10—C9—H9A	109.4
O1—C2—C1	119.11 (11)	N3—C9—H9B	109.4
C3—C2—C1	120.59 (11)	C10—C9—H9B	109.4
O2—C3—C4	122.81 (11)	H9A—C9—H9B	108.0
O2—C3—C2	117.46 (11)	C9—C10—H10A	109.5
C4—C3—C2	119.72 (11)	C9—C10—H10B	109.5
O3—C4—C3	116.43 (11)	H10A—C10—H10B	109.5
O3—C4—C5	123.27 (11)	C9—C10—H10C	109.5
C3—C4—C5	120.30 (12)	H10A—C10—H10C	109.5
C6—C5—C4	119.63 (12)	H10B—C10—H10C	109.5
C7—N1—N2—C8	−175.71 (11)	O3—C4—C5—C6	−179.39 (12)
C6—C1—C2—O1	179.53 (11)	C3—C4—C5—C6	0.03 (19)
C7—C1—C2—O1	−2.47 (18)	C4—C5—C6—C1	1.21 (19)
C6—C1—C2—C3	0.05 (18)	C2—C1—C6—C5	−1.25 (19)
C7—C1—C2—C3	178.06 (11)	C7—C1—C6—C5	−179.26 (12)
O1—C2—C3—O2	0.95 (18)	N2—N1—C7—C1	174.75 (11)
C1—C2—C3—O2	−179.58 (11)	C2—C1—C7—N1	167.00 (12)
O1—C2—C3—C4	−178.31 (11)	C6—C1—C7—N1	−15.04 (18)
C1—C2—C3—C4	1.16 (19)	C9—N3—C8—N2	173.77 (12)
O2—C3—C4—O3	−0.96 (18)	C9—N3—C8—S1	−7.36 (19)
C2—C3—C4—O3	178.26 (11)	N1—N2—C8—N3	−8.18 (17)
O2—C3—C4—C5	179.58 (12)	N1—N2—C8—S1	172.89 (9)
C2—C3—C4—C5	−1.20 (19)	C8—N3—C9—C10	−97.70 (16)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1o···O2	0.83 (1)	2.26 (2)	2.717 (1)	115 (2)
O1—H1o···S1i	0.83 (1)	2.55 (1)	3.291 (1)	150 (2)
O2—H2o···O3	0.84 (1)	2.31 (2)	2.745 (1)	112 (2)
O2—H2o···O1ii	0.84 (1)	2.07 (1)	2.832 (1)	151 (2)
O3—H3o···S1iii	0.84 (1)	2.36 (1)	3.189 (1)	170 (2)
N2—H2N···S1iv	0.87	2.62	3.480 (1)	171

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1O⋯O2	0.83 (1)	2.26 (2)	2.717 (1)	115 (2)
O1—H1O⋯S1i	0.83 (1)	2.55 (1)	3.291 (1)	150 (2)
O2—H2O⋯O3	0.84 (1)	2.31 (2)	2.745 (1)	112 (2)
O2—H2O⋯O1ii	0.84 (1)	2.07 (1)	2.832 (1)	151 (2)
O3—H3O⋯S1iii	0.84 (1)	2.36 (1)	3.189 (1)	170 (2)
N2—H2N⋯S1iv	0.87	2.62	3.480 (1)	171

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