(E)-1-(3-Eth­oxy-2-hy­droxy­benzyl­idene)thio­semicarbazide

Adabi Ardakani, A.; Kargar, H.; Kia, R.; Tahir, M.N.

doi:10.1107/S1600536812000487

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 68| Part 2| February 2012| Pages o340-o341

doi:10.1107/S1600536812000487

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(E)-1-(3-Ethoxy-2-hydroxybenzylidene)thiosemicarbazide

Amir Adabi Ardakani,^a ^* Hadi Kargar,^b Reza Kia ^c,^d and Muhammad Nawaz Tahir ^e ^*

^aArdakan Branch, Islamic Azad University, Ardakan, Iran, ^bDepartment of Chemistry, Payame Noor University, PO BOX 19395-3697 Tehran, I. R. of IRAN, ^cX-ray Crystallography Lab., Plasma Physics Research Center, Science and Research Branch, Islamic Azad University, Tehran, Iran, ^dDepartment of Chemistry, Science and Research Branch, Islamic Azad University, Tehran, Iran, and ^eDepartment of Physics, University of Sargodha, Punjab, Pakistan
^*Correspondence e-mail: A.Adabi@iauardakan.ac.ir, dmntahir_uos@yahoo.com

(Received 27 December 2011; accepted 5 January 2012; online 11 January 2012)

The title compound, C₁₀H₁₃N₃O₂S, crystallizes with two independent molecules (A and B) in the asymmetric unit. In the crystal, the A and B molecules are linked via pairs of N—H⋯O and O—H⋯S hydrogen bonds, forming dimers with R₂²(14) and R₂²(6) ring motifs. These dimers are linked via a pair of N—H⋯S hydrogen bonds with an R₂²(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. (2010a ,b ).

Experimental

Crystal data

C₁₀H₁₃N₃O₂S
M_r = 239.29
Monoclinic, P 2₁
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[F² > 2σ(F²)] = 0.056
wR(F²) = 0.119
S = 0.92
5428 reflections
293 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.21 e Å⁻³
Δρ_min = −0.21 e Å⁻³
Absolute structure: Flack (1983 ), 2232 Friedel pairs
Flack parameter: 0.54 (11)

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⋯S1^iv	0.88	2.55	3.398 (5)	161
Symmetry codes: (i) x+1, y, z; (ii) x-1, y, z; (iii) x+1, y, z-1; (iv) x-1, y, z+1.

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 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812000487/su2360sup1.cif

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

Supporting information file. DOI: 10.1107/S1600536812000487/su2360Isup3.cml

checkCIF report

Comment top

Thiosemicarbazones constitute an important class of N,S donor ligands due to their propensity to react with a wide range of metals (Casas et al., 2000). Thiosemicarbazones exhibit various biological activities and have therefore attracted considerable pharmaceutical interest (Maccioni et al., 2003; Ferrari et al., 2000). Herein, we report on the crystal structure of the new title thiosemicarbazone compound.

The title compound crystallized with two independent molecules (A and B) in the asymmetric unit, Fig. 1. The bond lengths (Allen et al., 1987) and angles are within the normal ranges and are comparable to those observed for related structures (Kargar et al., 2010a,b).

In the crystal, the A and B molecules are linked via pairs of N-H···O and O-H···S hydrogen bonds (Table 1 and Fig. 2) to form dimers, with R²₂(14) and R²₂(6) ring motifs (Bernstein et al., 1995). These dimers are further linked via a pair of N-H···S hydrogen bonds, with an R²₂(8) ring motif, to form chains that extend in direction [0 0 1] (Table 1 and Fig. 2).

The crystal was refined as an inversion twin with a final refined BASF ratio of 0.54 (11)/0.46 (11) for 2232 Friedel pairs.

Related literature top

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. (2010a,b).

Experimental top

A mixture of 3-ethoxysalicylalehyde (0.01 mol) and hydrazinecarbothioamide (0.01 mol) in 20 ml of ethanol was refluxed for about 2 h. On cooling, the solid separated was filtered and recrystallized from ethanol. Colourless plate-like crystals of the title compound, suitable for X-ray diffraction, were obtained by slow evaporation of a solution in ethanol.

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); 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 (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of the two independent molecules of the title compound, showing 40% probability displacement ellipsoids and the atomic numbering.
	Fig. 2. A partial crystal packing diagram of the title compound, viewed down the a-axis, showing a one-dimensional extended chain along the c-axis formed via intermolecular O—H···S, N—H···O, and N—H···S hydrogen bonds [dashed lines; see Table 1 for details; only the H atoms involved in these interactions are shown].

(E)-1-(3-Ethoxy-2-hydroxybenzylidene)thiosemicarbazide top

Crystal data top

C₁₀H₁₃N₃O₂S	F(000) = 504
M_r = 239.29	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.0341P)²] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.119	(Δ/σ)_max < 0.001
S = 0.92	Δρ_max = 0.21 e Å⁻³
5428 reflections	Δρ_min = −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	Absolute structure parameter: 0.54 (11)

Crystal data top

C₁₀H₁₃N₃O₂S	V = 1260.91 (11) Å³
M_r = 239.29	Z = 4
Monoclinic, P2₁	Mo Kα radiation
a = 6.0728 (3) Å	µ = 0.25 mm⁻¹
b = 16.1595 (8) Å	T = 291 K
c = 12.8490 (6) Å	0.24 × 0.14 × 0.08 mm
β = 90.238 (3)°

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	5428 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	2303 reflections with I > 2σ(I)
T_min = 0.800, T_max = 0.926	R_int = 0.075
12062 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.056	H-atom parameters constrained
wR(F²) = 0.119	Δρ_max = 0.21 e Å⁻³
S = 0.92	Δρ_min = −0.21 e Å⁻³
5428 reflections	Absolute structure: Flack (1983), 2232 Friedel pairs
293 parameters	Absolute structure parameter: 0.54 (11)
1 restraint

Special details top

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.

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

	x	y	z	U_iso*/U_eq
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)

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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···S1^iv	0.88	2.55	3.398 (5)	161

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

Experimental details

Crystal data
Chemical formula	C₁₀H₁₃N₃O₂S
M_r	239.29
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	291
a, b, c (Å)	6.0728 (3), 16.1595 (8), 12.8490 (6)
β (°)	90.238 (3)
V (Å³)	1260.91 (11)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.25
Crystal size (mm)	0.24 × 0.14 × 0.08

Data collection
Diffractometer	Bruker SMART APEX CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.800, 0.926
No. of measured, independent and observed [I > 2σ(I)] reflections	12062, 5428, 2303
R_int	0.075
(sin θ/λ)_max (Å⁻¹)	0.667

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.056, 0.119, 0.92
No. of reflections	5428
No. of parameters	293
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.21, −0.21
Absolute structure	Flack (1983), 2232 Friedel pairs
Absolute structure parameter	0.54 (11)

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

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···S1^iv	0.88	2.55	3.398 (5)	161

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

Acknowledgements

AAA thanks the Islamic Azad University, Ardakan Branch (this paper was extracted from the research project). HK thanks PNU for financial support. MNT thanks Sargodha University for research facilities.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19. CrossRef Web of Science Google Scholar
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573. CrossRef CAS Web of Science Google Scholar
Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Casas, J. S., Garcia-Tasende, M. S. & Sordo, J. (2000). Coord. Chem. Rev. 209, 197–261. Web of Science CrossRef CAS Google Scholar
Ferrari, M. B., Capacchi, S., Reffo, G., Pelosi, G., Tarasconi, P., Albertini, R., Pinelli, S. & Lunghi, P. (2000). J. Inorg. Biochem. 81, 89–97. Web of Science CSD CrossRef PubMed CAS Google Scholar
Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
Kargar, H., Kia, R., Akkurt, M. & Büyükgüngör, O. (2010a). Acta Cryst. E66, o2999. Web of Science CSD CrossRef IUCr Journals Google Scholar
Kargar, H., Kia, R., Akkurt, M. & Büyükgüngör, O. (2010b). Acta Cryst. E66, o2982. Web of Science CSD CrossRef IUCr Journals Google Scholar
Maccioni, E., Cardia, M. C., Distinto, S., Bonsignore, L. & De Logu, A. (2003). Farmaco 58, 951–959. CrossRef PubMed CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar