(E)-1-(2,4,6-Trihy­droxy­benzyl­idene)-4-ethyl­thio­semicarbazide dihydrate

Shawish, H.B.; Tan, K.W.; Maah, M.J.; Ng, S.W.

doi:10.1107/S1600536810030783

organic compounds

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ISSN: 2056-9890

Volume 66| Part 9| September 2010| Page o2230

https://doi.org/10.1107/S1600536810030783

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(E)-1-(2,4,6-Trihydroxybenzylidene)-4-ethylthiosemicarbazide dihydrate

Hana Bashir Shawish,^a Kong Wai Tan,^a M. Jamil Maah ^a ^* and Seik Weng Ng ^a

^aDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: mjamil@um.edu.my

(Received 1 August 2010; accepted 2 August 2010; online 11 August 2010)

In the title molecule, C₁₀H₁₃N₃O₃S·2H₂O, the thiosemicarbazide =N—NH—C(=S)—NH– fragment [torsion angle = 0.2 (1)°] is nearly coplanar with the benzene ring [dihedral angle = 2.4 (1)°]. The benzene ring and semicarbazide moiety are located on opposite sites of the C=N bond, showing an E configuration. The hydroxy, imino and water H atoms are engaged in extensive hydrogen bonding, forming a three-dimensional network.

Related literature

For the crystal structure of a related compound, 1-(2,3,4-trihydroxybenzylidene)-4-ethylthiosemicarbazide, see: Shawish et al. (2010 ).

Experimental

Crystal data

C₁₀H₁₃N₃O₃S·2H₂O
M_r = 291.33
Monoclinic, P 2₁
a = 4.6645 (4) Å
b = 10.4006 (9) Å
c = 13.5381 (11) Å
β = 98.674 (1)°
V = 649.27 (10) Å³
Z = 2
Mo Kα radiation
μ = 0.27 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 = 0.923, T_max = 0.973
6232 measured reflections
2937 independent reflections
2826 reflections with I > 2σ(I)
R_int = 0.025

Refinement

R[F² > 2σ(F²)] = 0.028
wR(F²) = 0.074
S = 1.03
2937 reflections
208 parameters
12 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.24 e Å⁻³
Δρ_min = −0.19 e Å⁻³
Absolute structure: Flack (1983 ), 1370 Friedel pairs
Flack parameter: −0.05 (6)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1o⋯N1	0.85 (1)	1.99 (2)	2.722 (2)	144 (2)
O2—H2o⋯O1ⁱ	0.83 (1)	2.27 (2)	2.955 (2)	140 (2)
O3—H3o⋯O1W	0.85 (2)	1.76 (2)	2.598 (2)	174 (2)
O1w—H11⋯O2w	0.84 (1)	1.94 (1)	2.785 (2)	177 (3)
O1w—H12⋯O3ⁱⁱ	0.84 (1)	2.22 (1)	3.002 (2)	155 (2)
O2w—H21⋯S1ⁱⁱⁱ	0.84 (1)	2.45 (1)	3.279 (1)	169 (2)
O2w—H22⋯S1^iv	0.84 (1)	2.49 (1)	3.292 (1)	162 (2)
N2—H2n⋯O2w^v	0.86 (1)	2.13 (1)	2.965 (2)	166 (2)
N3—H3n⋯O2^vi	0.86 (1)	2.26 (2)	2.934 (2)	136 (2)
Symmetry codes: (i) $[-x+1, y-{\script{1\over 2}}, -z+1]$ ; (ii) x-1, y, z; (iii) x-2, y-1, z; (iv) x-1, y-1, z; (v) $[-x+1, y+{\script{1\over 2}}, -z]$ ; (vi) $[-x+2, y+{\script{1\over 2}}, -z+1]$ .

Data collection: APEX2 (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 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536810030783/xu5011sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810030783/xu5011Isup2.hkl

checkCIF report

Related literature top

For the crystal structure of a related compound, 1-(2,3,4-trihydroxybenzylidene)-4-ethylthiosemicarbazide, see: Shawish et al. (2010).

Experimental top

2,4,6-Trihydroxybenzaldehyde (1.54 g, 10 mmol) and 4-ethylthiosemicarbazide (1.19 g, 1 mmol) were heated in ethanol (20 ml) for 2 h; acetic acid (0.5 ml) was also added. A brown solid separated from the cool solution; this was recrystallized from methanol.

Structure description top

For the crystal structure of a related compound, 1-(2,3,4-trihydroxybenzylidene)-4-ethylthiosemicarbazide, see: Shawish et al. (2010).

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); 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).

Figures top

Fig. 1. Thermal ellipsoid plot (Barbour, 2001) of C₁₀H₁₃N₃O₃S^.2H₂O at the 70% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.

(E)-1-(2,4,6-Trihydroxybenzylidene)-4-ethylthiosemicarbazide dihydrate top

Crystal data top

C₁₀H₁₃N₃O₃S·2H₂O	F(000) = 308
M_r = 291.33	D_x = 1.490 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 3449 reflections
a = 4.6645 (4) Å	θ = 2.5–28.2°
b = 10.4006 (9) Å	µ = 0.27 mm⁻¹
c = 13.5381 (11) Å	T = 100 K
β = 98.674 (1)°	Prism, yellow
V = 649.27 (10) Å³	0.30 × 0.20 × 0.10 mm
Z = 2

Data collection top

Bruker SMART APEX diffractometer	2937 independent reflections
Radiation source: fine-focus sealed tube	2826 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.025
ω scans	θ_max = 27.5°, θ_min = 1.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −6→5
T_min = 0.923, T_max = 0.973	k = −13→13
6232 measured reflections	l = −17→17

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.028	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.074	w = 1/[σ²(F_o²) + (0.0442P)² + 0.0466P] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max = 0.001
2937 reflections	Δρ_max = 0.24 e Å⁻³
208 parameters	Δρ_min = −0.19 e Å⁻³
12 restraints	Absolute structure: Flack (1983), 1370 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.05 (6)

Crystal data top

C₁₀H₁₃N₃O₃S·2H₂O	V = 649.27 (10) Å³
M_r = 291.33	Z = 2
Monoclinic, P2₁	Mo Kα radiation
a = 4.6645 (4) Å	µ = 0.27 mm⁻¹
b = 10.4006 (9) Å	T = 100 K
c = 13.5381 (11) Å	0.30 × 0.20 × 0.10 mm
β = 98.674 (1)°

Data collection top

Bruker SMART APEX diffractometer	2937 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2826 reflections with I > 2σ(I)
T_min = 0.923, T_max = 0.973	R_int = 0.025
6232 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.028	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.074	Δρ_max = 0.24 e Å⁻³
S = 1.03	Δρ_min = −0.19 e Å⁻³
2937 reflections	Absolute structure: Flack (1983), 1370 Friedel pairs
208 parameters	Absolute structure parameter: −0.05 (6)
12 restraints

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
S1	1.52160 (9)	1.00002 (4)	0.04613 (3)	0.01642 (10)
O1	1.0480 (3)	0.82234 (12)	0.44254 (9)	0.0175 (3)
O2	0.4114 (3)	0.51122 (13)	0.53548 (9)	0.0185 (3)
O3	0.5005 (3)	0.56687 (12)	0.18897 (9)	0.0171 (3)
O1W	0.0357 (3)	0.42702 (13)	0.15044 (10)	0.0204 (3)
O2W	0.0077 (3)	0.21977 (12)	0.01907 (10)	0.0197 (3)
N1	1.1216 (3)	0.83376 (14)	0.24708 (10)	0.0136 (3)
N2	1.2187 (3)	0.87300 (14)	0.16047 (10)	0.0139 (3)
N3	1.5378 (3)	1.01558 (15)	0.24590 (10)	0.0147 (3)
C1	0.8575 (3)	0.72575 (16)	0.41274 (13)	0.0133 (3)
C2	0.7317 (4)	0.66456 (16)	0.48651 (13)	0.0152 (3)
H2	0.7859	0.6873	0.5547	0.018*
C3	0.5256 (4)	0.56959 (17)	0.45936 (12)	0.0149 (3)
C4	0.4389 (4)	0.53585 (15)	0.36022 (12)	0.0142 (3)
H4	0.2932	0.4726	0.3427	0.017*
C5	0.5697 (4)	0.59662 (15)	0.28686 (13)	0.0136 (3)
C6	0.7848 (4)	0.69196 (15)	0.31126 (13)	0.0126 (3)
C7	0.9158 (4)	0.74927 (16)	0.23201 (13)	0.0135 (3)
H7	0.8477	0.7237	0.1652	0.016*
C8	1.4257 (3)	0.96307 (15)	0.15970 (13)	0.0131 (3)
C9	1.7695 (4)	1.11131 (17)	0.25974 (13)	0.0179 (4)
H9A	1.8548	1.1188	0.1973	0.021*
H9B	1.9242	1.0822	0.3133	0.021*
C10	1.6620 (5)	1.24156 (18)	0.28688 (17)	0.0274 (4)
H10A	1.8236	1.3028	0.2953	0.041*
H10B	1.5812	1.2350	0.3495	0.041*
H10C	1.5113	1.2715	0.2335	0.041*
H1O	1.132 (4)	0.846 (2)	0.3945 (12)	0.022 (6)*
H2O	0.280 (4)	0.462 (2)	0.5106 (17)	0.036 (7)*
H3O	0.356 (4)	0.517 (2)	0.1785 (17)	0.029 (6)*
H11	0.024 (5)	0.3659 (19)	0.1092 (18)	0.048 (8)*
H12	−0.122 (4)	0.467 (2)	0.1412 (19)	0.059 (10)*
H21	−0.127 (3)	0.1711 (18)	0.0304 (18)	0.029 (7)*
H22	0.162 (3)	0.178 (2)	0.022 (2)	0.047 (8)*
H2N	1.140 (4)	0.841 (2)	0.1046 (10)	0.020 (5)*
H3N	1.476 (4)	0.9852 (19)	0.2978 (10)	0.014 (5)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.01776 (19)	0.0203 (2)	0.01189 (19)	−0.00408 (18)	0.00442 (14)	0.00107 (17)
O1	0.0181 (6)	0.0191 (6)	0.0151 (6)	−0.0046 (5)	0.0025 (5)	−0.0017 (5)
O2	0.0223 (6)	0.0215 (6)	0.0122 (6)	−0.0044 (6)	0.0042 (5)	0.0020 (5)
O3	0.0195 (6)	0.0208 (6)	0.0113 (6)	−0.0057 (5)	0.0031 (5)	−0.0035 (5)
O1W	0.0173 (7)	0.0228 (7)	0.0204 (7)	−0.0006 (5)	0.0009 (5)	−0.0031 (5)
O2W	0.0190 (7)	0.0185 (7)	0.0215 (7)	−0.0023 (6)	0.0033 (6)	0.0019 (5)
N1	0.0141 (7)	0.0146 (6)	0.0128 (7)	0.0017 (5)	0.0042 (6)	0.0024 (5)
N2	0.0155 (7)	0.0167 (7)	0.0097 (7)	−0.0028 (5)	0.0029 (6)	0.0004 (5)
N3	0.0158 (7)	0.0176 (7)	0.0117 (6)	−0.0026 (6)	0.0052 (5)	−0.0001 (6)
C1	0.0114 (8)	0.0134 (7)	0.0150 (8)	0.0024 (6)	0.0014 (6)	−0.0002 (6)
C2	0.0165 (9)	0.0182 (8)	0.0102 (8)	0.0027 (7)	0.0001 (6)	−0.0001 (6)
C3	0.0168 (8)	0.0146 (8)	0.0142 (8)	0.0038 (7)	0.0057 (6)	0.0033 (6)
C4	0.0139 (8)	0.0136 (8)	0.0153 (8)	−0.0008 (6)	0.0033 (6)	−0.0008 (6)
C5	0.0141 (8)	0.0137 (7)	0.0133 (8)	0.0026 (6)	0.0033 (6)	0.0004 (6)
C6	0.0115 (8)	0.0129 (7)	0.0137 (8)	0.0025 (6)	0.0027 (6)	0.0011 (6)
C7	0.0150 (8)	0.0141 (8)	0.0115 (8)	0.0028 (6)	0.0020 (6)	0.0000 (6)
C8	0.0118 (8)	0.0134 (7)	0.0146 (8)	0.0019 (6)	0.0033 (6)	0.0020 (6)
C9	0.0164 (9)	0.0202 (8)	0.0171 (9)	−0.0032 (7)	0.0031 (7)	−0.0027 (7)
C10	0.0308 (11)	0.0174 (9)	0.0363 (12)	−0.0024 (8)	0.0122 (9)	0.0012 (8)

Geometric parameters (Å, º) top

S1—C8	1.7085 (17)	N3—H3N	0.86 (1)
O1—C1	1.362 (2)	C1—C2	1.387 (2)
O1—H1O	0.85 (1)	C1—C6	1.409 (2)
O2—C3	1.3710 (19)	C2—C3	1.389 (2)
O2—H2O	0.83 (1)	C2—H2	0.9500
O3—C5	1.352 (2)	C3—C4	1.387 (2)
O3—H3O	0.85 (1)	C4—C5	1.393 (2)
O1W—H11	0.84 (1)	C4—H4	0.9500
O1W—H12	0.84 (1)	C5—C6	1.414 (2)
O2W—H21	0.84 (1)	C6—C7	1.442 (2)
O2W—H22	0.84 (1)	C7—H7	0.9500
N1—C7	1.294 (2)	C9—C10	1.509 (3)
N1—N2	1.3809 (19)	C9—H9A	0.9900
N2—C8	1.346 (2)	C9—H9B	0.9900
N2—H2N	0.86 (1)	C10—H10A	0.9800
N3—C8	1.323 (2)	C10—H10B	0.9800
N3—C9	1.461 (2)	C10—H10C	0.9800

C1—O1—H1O	110.3 (16)	O3—C5—C4	121.98 (15)
C3—O2—H2O	108.4 (17)	O3—C5—C6	116.47 (15)
C5—O3—H3O	111.8 (16)	C4—C5—C6	121.55 (15)
H11—O1W—H12	107.8 (15)	C1—C6—C5	117.44 (15)
H21—O2W—H22	109.8 (15)	C1—C6—C7	123.77 (15)
C7—N1—N2	113.40 (14)	C5—C6—C7	118.80 (15)
C8—N2—N1	122.67 (15)	N1—C7—C6	123.43 (15)
C8—N2—H2N	118.4 (15)	N1—C7—H7	118.3
N1—N2—H2N	118.9 (15)	C6—C7—H7	118.3
C8—N3—C9	125.54 (14)	N3—C8—N2	117.97 (15)
C8—N3—H3N	115.7 (14)	N3—C8—S1	125.35 (13)
C9—N3—H3N	118.6 (14)	N2—C8—S1	116.68 (13)
O1—C1—C2	116.95 (15)	N3—C9—C10	112.11 (15)
O1—C1—C6	121.56 (15)	N3—C9—H9A	109.2
C2—C1—C6	121.46 (15)	C10—C9—H9A	109.2
C1—C2—C3	119.14 (15)	N3—C9—H9B	109.2
C1—C2—H2	120.4	C10—C9—H9B	109.2
C3—C2—H2	120.4	H9A—C9—H9B	107.9
O2—C3—C4	121.71 (16)	C9—C10—H10A	109.5
O2—C3—C2	116.61 (15)	C9—C10—H10B	109.5
C4—C3—C2	121.67 (15)	H10A—C10—H10B	109.5
C3—C4—C5	118.68 (16)	C9—C10—H10C	109.5
C3—C4—H4	120.7	H10A—C10—H10C	109.5
C5—C4—H4	120.7	H10B—C10—H10C	109.5

C7—N1—N2—C8	178.00 (15)	O3—C5—C6—C1	179.15 (15)
O1—C1—C2—C3	176.95 (15)	C4—C5—C6—C1	−1.5 (2)
C6—C1—C2—C3	−1.2 (2)	O3—C5—C6—C7	−0.6 (2)
C1—C2—C3—O2	179.17 (15)	C4—C5—C6—C7	178.74 (15)
C1—C2—C3—C4	−1.1 (2)	N2—N1—C7—C6	178.51 (14)
O2—C3—C4—C5	−178.27 (15)	C1—C6—C7—N1	2.9 (3)
C2—C3—C4—C5	2.0 (2)	C5—C6—C7—N1	−177.42 (15)
C3—C4—C5—O3	178.64 (15)	C9—N3—C8—N2	177.96 (15)
C3—C4—C5—C6	−0.6 (2)	C9—N3—C8—S1	−2.1 (2)
O1—C1—C6—C5	−175.63 (14)	N1—N2—C8—N3	−0.2 (2)
C2—C1—C6—C5	2.5 (2)	N1—N2—C8—S1	179.78 (12)
O1—C1—C6—C7	4.1 (3)	C8—N3—C9—C10	110.57 (19)
C2—C1—C6—C7	−177.80 (15)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1o···N1	0.85 (1)	1.99 (2)	2.722 (2)	144 (2)
O2—H2o···O1ⁱ	0.83 (1)	2.27 (2)	2.955 (2)	140 (2)
O3—H3o···O1W	0.85 (2)	1.76 (2)	2.598 (2)	174 (2)
O1w—H11···O2w	0.84 (1)	1.94 (1)	2.785 (2)	177 (3)
O1w—H12···O3ⁱⁱ	0.84 (1)	2.22 (1)	3.002 (2)	155 (2)
O2w—H21···S1ⁱⁱⁱ	0.84 (1)	2.45 (1)	3.279 (1)	169 (2)
O2w—H22···S1^iv	0.84 (1)	2.49 (1)	3.292 (1)	162 (2)
N2—H2n···O2w^v	0.86 (1)	2.13 (1)	2.965 (2)	166 (2)
N3—H3n···O2^vi	0.86 (1)	2.26 (2)	2.934 (2)	136 (2)

Symmetry codes: (i) −x+1, y−1/2, −z+1; (ii) x−1, y, z; (iii) x−2, y−1, z; (iv) x−1, y−1, z; (v) −x+1, y+1/2, −z; (vi) −x+2, y+1/2, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₀H₁₃N₃O₃S·2H₂O
M_r	291.33
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	100
a, b, c (Å)	4.6645 (4), 10.4006 (9), 13.5381 (11)
β (°)	98.674 (1)
V (Å³)	649.27 (10)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.27
Crystal size (mm)	0.30 × 0.20 × 0.10

Data collection
Diffractometer	Bruker SMART APEX diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.923, 0.973
No. of measured, independent and observed [I > 2σ(I)] reflections	6232, 2937, 2826
R_int	0.025
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.028, 0.074, 1.03
No. of reflections	2937
No. of parameters	208
No. of restraints	12
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.24, −0.19
Absolute structure	Flack (1983), 1370 Friedel pairs
Absolute structure parameter	−0.05 (6)

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1o···N1	0.85 (1)	1.99 (2)	2.722 (2)	144 (2)
O2—H2o···O1ⁱ	0.83 (1)	2.27 (2)	2.955 (2)	140 (2)
O3—H3o···O1W	0.85 (2)	1.76 (2)	2.598 (2)	174 (2)
O1w—H11···O2w	0.84 (1)	1.94 (1)	2.785 (2)	177 (3)
O1w—H12···O3ⁱⁱ	0.84 (1)	2.22 (1)	3.002 (2)	155 (2)
O2w—H21···S1ⁱⁱⁱ	0.84 (1)	2.45 (1)	3.279 (1)	169 (2)
O2w—H22···S1^iv	0.84 (1)	2.49 (1)	3.292 (1)	162 (2)
N2—H2n···O2w^v	0.86 (1)	2.13 (1)	2.965 (2)	166 (2)
N3—H3n···O2^vi	0.86 (1)	2.26 (2)	2.934 (2)	136 (2)

Symmetry codes: (i) −x+1, y−1/2, −z+1; (ii) x−1, y, z; (iii) x−2, y−1, z; (iv) x−1, y−1, z; (v) −x+1, y+1/2, −z; (vi) −x+2, y+1/2, −z+1.

Acknowledgements

We thank the University of Malaya (PS354/2009) and MOHE (FRGS-FP001/2009) for supporting this study. HBS also thanks the Libyan People's Bureau in Malaysia for a scholarship.

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