2,4-Dihydroxy-benzaldehyde 4-ethyl-thio-semicarbazone.

The mol-ecular conformation of the title compound, C(10)H(13)N(3)O(2)S, is stabilized by an intramolecular O-H⋯N hydrogen bond. Adjacent mol-ecules are linked by O-H⋯O hydrogen bonds to furnish a zigzag chain.

Related literature

For the structure of 3,4-dihydroxy­benzaldehyde 4-ethyl­thio­semicarbazone, see: Kayed et al. (2008 ▶).

Experimental

Crystal data

C10H13N3O2S

M = 239.29

Monoclinic,

a = 4.6592 (6) Å

b = 24.067 (3) Å

c = 10.047 (1) Å

β = 99.060 (2)°

V = 1112.5 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.28 mm−1

T = 100 (2) K

0.40 × 0.12 × 0.06 mm

Data collection

Bruker SMART APEX diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.896, T max = 0.983

6303 measured reflections

2517 independent reflections

1972 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.109

S = 1.08

2517 reflections

148 parameters

H-atom parameters constrained

Δρmax = 0.38 e Å−3

Δρmin = −0.25 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); 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, 2008 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053680803300X/bt2806sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680803300X/bt2806Isup2.hkl

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

C10H13N3O2S	F(000) = 504
Mr = 239.29	Dx = 1.429 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 1634 reflections
a = 4.6592 (6) Å	θ = 2.6–28.1°
b = 24.067 (3) Å	µ = 0.28 mm−1
c = 10.047 (1) Å	T = 100 K
β = 99.060 (2)°	Plate, yellow
V = 1112.5 (2) Å3	0.40 × 0.12 × 0.06 mm
Z = 4

Bruker SMART APEX diffractometer	2517 independent reflections
Radiation source: fine-focus sealed tube	1972 reflections with I > 2σ(I)
graphite	Rint = 0.028
ω scans	θmax = 27.5°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −6→4
Tmin = 0.896, Tmax = 0.983	k = −30→31
6303 measured reflections	l = −13→12

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.109	H-atom parameters constrained
S = 1.08	w = 1/[σ2(Fo2) + (0.0512P)2 + 0.3651P] where P = (Fo2 + 2Fc2)/3
2517 reflections	(Δ/σ)max = 0.001
148 parameters	Δρmax = 0.38 e Å−3
0 restraints	Δρmin = −0.25 e Å−3

	x	y	z	Uiso*/Ueq
S1	1.01421 (11)	0.514276 (19)	0.28484 (5)	0.02112 (15)
O1	0.1480 (3)	0.32859 (6)	0.28304 (13)	0.0240 (3)
H1	0.2707	0.3544	0.2908	0.036*
O2	−0.4004 (3)	0.21979 (5)	0.53651 (13)	0.0238 (3)
H2	−0.4152	0.2117	0.6165	0.036*
N1	0.6825 (4)	0.43087 (7)	0.17727 (16)	0.0225 (4)
H1N	0.5495	0.4056	0.1845	0.027*
N2	0.6791 (3)	0.44770 (6)	0.40159 (15)	0.0175 (3)
H2N	0.7378	0.4666	0.4760	0.021*
N3	0.4854 (3)	0.40468 (6)	0.40248 (15)	0.0169 (3)
C1	0.6265 (5)	0.39432 (9)	−0.0504 (2)	0.0270 (5)
H1A	0.6985	0.3971	−0.1367	0.040*
H1B	0.4169	0.4015	−0.0644	0.040*
H1C	0.6644	0.3569	−0.0132	0.040*
C2	0.7804 (5)	0.43673 (9)	0.0471 (2)	0.0276 (5)
H2A	0.9932	0.4309	0.0578	0.033*
H2B	0.7371	0.4747	0.0115	0.033*
C3	0.7800 (4)	0.46113 (7)	0.28620 (18)	0.0174 (4)
C4	0.3905 (4)	0.39384 (7)	0.51361 (17)	0.0162 (4)
H4	0.4568	0.4152	0.5920	0.019*
C5	0.1834 (4)	0.34936 (7)	0.51966 (18)	0.0154 (4)
C6	0.0690 (4)	0.31772 (7)	0.40586 (18)	0.0174 (4)
C7	−0.1245 (4)	0.27525 (8)	0.41357 (19)	0.0195 (4)
H7	−0.1983	0.2545	0.3352	0.023*
C8	−0.2121 (4)	0.26265 (7)	0.53563 (18)	0.0179 (4)
C9	−0.1092 (4)	0.29412 (7)	0.65039 (18)	0.0181 (4)
H9	−0.1729	0.2864	0.7338	0.022*
C10	0.0857 (4)	0.33653 (7)	0.64102 (18)	0.0171 (4)
H10	0.1560	0.3577	0.7192	0.021*

	U11	U22	U33	U12	U13	U23
S1	0.0235 (3)	0.0188 (2)	0.0214 (2)	−0.0054 (2)	0.00430 (19)	0.00073 (18)
O1	0.0316 (9)	0.0240 (7)	0.0169 (6)	−0.0099 (6)	0.0059 (6)	−0.0026 (5)
O2	0.0275 (8)	0.0207 (7)	0.0225 (7)	−0.0089 (6)	0.0019 (6)	0.0036 (5)
N1	0.0235 (9)	0.0242 (8)	0.0207 (8)	−0.0087 (7)	0.0063 (7)	−0.0028 (7)
N2	0.0181 (8)	0.0176 (8)	0.0167 (7)	−0.0047 (6)	0.0022 (6)	−0.0009 (6)
N3	0.0154 (8)	0.0139 (7)	0.0211 (8)	−0.0016 (6)	0.0019 (6)	0.0017 (6)
C1	0.0302 (12)	0.0283 (11)	0.0228 (10)	−0.0037 (9)	0.0056 (9)	−0.0022 (8)
C2	0.0301 (12)	0.0332 (11)	0.0209 (10)	−0.0089 (10)	0.0081 (9)	−0.0025 (8)
C3	0.0141 (10)	0.0168 (9)	0.0209 (9)	0.0029 (7)	0.0017 (7)	0.0019 (7)
C4	0.0151 (10)	0.0162 (8)	0.0165 (9)	0.0004 (7)	0.0004 (7)	−0.0011 (7)
C5	0.0138 (9)	0.0133 (8)	0.0185 (9)	0.0021 (7)	0.0006 (7)	0.0002 (7)
C6	0.0176 (10)	0.0179 (9)	0.0166 (9)	0.0025 (7)	0.0027 (7)	0.0007 (7)
C7	0.0208 (10)	0.0169 (9)	0.0195 (9)	−0.0012 (8)	−0.0010 (8)	−0.0014 (7)
C8	0.0154 (10)	0.0139 (8)	0.0232 (9)	−0.0007 (7)	−0.0005 (8)	0.0031 (7)
C9	0.0184 (10)	0.0190 (9)	0.0168 (9)	0.0012 (7)	0.0021 (7)	0.0033 (7)
C10	0.0180 (10)	0.0170 (9)	0.0155 (8)	0.0015 (8)	−0.0003 (7)	−0.0017 (7)

S1—C3	1.6826 (19)	C1—H1C	0.9800
O1—C6	1.367 (2)	C2—H2A	0.9900
O1—H1	0.8400	C2—H2B	0.9900
O2—C8	1.355 (2)	C4—C5	1.449 (2)
O2—H2	0.8400	C4—H4	0.9500
N1—C3	1.333 (2)	C5—C10	1.401 (2)
N1—C2	1.458 (2)	C5—C6	1.407 (2)
N1—H1N	0.8800	C6—C7	1.373 (3)
N2—C3	1.357 (2)	C7—C8	1.386 (3)
N2—N3	1.374 (2)	C7—H7	0.9500
N2—H2N	0.8800	C8—C9	1.400 (3)
N3—C4	1.291 (2)	C9—C10	1.379 (3)
C1—C2	1.515 (3)	C9—H9	0.9500
C1—H1A	0.9800	C10—H10	0.9500
C1—H1B	0.9800
C6—O1—H1	109.5	N2—C3—S1	120.03 (14)
C8—O2—H2	109.5	N3—C4—C5	120.45 (16)
C3—N1—C2	124.66 (16)	N3—C4—H4	119.8
C3—N1—H1N	117.7	C5—C4—H4	119.8
C2—N1—H1N	117.7	C10—C5—C6	117.04 (17)
C3—N2—N3	120.08 (15)	C10—C5—C4	120.59 (16)
C3—N2—H2N	120.0	C6—C5—C4	122.37 (16)
N3—N2—H2N	120.0	O1—C6—C7	117.76 (17)
C4—N3—N2	118.21 (15)	O1—C6—C5	120.57 (17)
C2—C1—H1A	109.5	C7—C6—C5	121.67 (17)
C2—C1—H1B	109.5	C6—C7—C8	120.03 (17)
H1A—C1—H1B	109.5	C6—C7—H7	120.0
C2—C1—H1C	109.5	C8—C7—H7	120.0
H1A—C1—H1C	109.5	O2—C8—C7	116.98 (17)
H1B—C1—H1C	109.5	O2—C8—C9	123.01 (17)
N1—C2—C1	109.36 (17)	C7—C8—C9	120.00 (17)
N1—C2—H2A	109.8	C10—C9—C8	119.21 (17)
C1—C2—H2A	109.8	C10—C9—H9	120.4
N1—C2—H2B	109.8	C8—C9—H9	120.4
C1—C2—H2B	109.8	C9—C10—C5	122.00 (17)
H2A—C2—H2B	108.3	C9—C10—H10	119.0
N1—C3—N2	116.86 (17)	C5—C10—H10	119.0
N1—C3—S1	123.11 (14)
C3—N2—N3—C4	−178.76 (17)	C10—C5—C6—C7	−1.5 (3)
C3—N1—C2—C1	178.52 (18)	C4—C5—C6—C7	179.20 (17)
C2—N1—C3—N2	−175.78 (18)	O1—C6—C7—C8	−179.83 (17)
C2—N1—C3—S1	4.9 (3)	C5—C6—C7—C8	0.1 (3)
N3—N2—C3—N1	0.0 (2)	C6—C7—C8—O2	−179.15 (16)
N3—N2—C3—S1	179.30 (13)	C6—C7—C8—C9	1.6 (3)
N2—N3—C4—C5	179.27 (15)	O2—C8—C9—C10	179.01 (17)
N3—C4—C5—C10	178.30 (17)	C7—C8—C9—C10	−1.8 (3)
N3—C4—C5—C6	−2.4 (3)	C8—C9—C10—C5	0.3 (3)
C10—C5—C6—O1	178.39 (16)	C6—C5—C10—C9	1.3 (3)
C4—C5—C6—O1	−0.9 (3)	C4—C5—C10—C9	−179.39 (17)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N3	0.84	1.84	2.583 (2)	147
O2—H2···O1i	0.84	1.92	2.714 (2)	158

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N3	0.84	1.84	2.583 (2)	147
O2—H2⋯O1i	0.84	1.92	2.714 (2)	158

Symmetry code: (i) .