1-(2-Chloro­phen­yl)-3-(2-ethyl­hexa­noyl)thio­urea

Santhakumari, R.; Selvanayagam, S.; Ramamurthi, K.; Radha, N.; Yamin, B.M.

doi:10.1107/S160053681301828X

organic compounds

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ISSN: 2056-9890

Volume 69| Part 8| August 2013| Page o1220

doi:10.1107/S160053681301828X

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1-(2-Chlorophenyl)-3-(2-ethylhexanoyl)thiourea

R. Santhakumari,^a ^* S. Selvanayagam,^b K. Ramamurthi,^c N. Radha ^d and Bohari M. Yamin ^e

^aDepartment of Physics, Government Arts College for Women (Autonomous), Pudukkottai 622 001, India, ^bDepartment of Physics, Kalasalingam University, Krishnankoil 626 126, India, ^cDepartment of Physics and Nanotechnology, SRM University, Kattankulathur 603 203, India, ^dDepartment of Chemistry, Government Arts College, Karaikudi 630 303, India, and ^eSchool of Chemical Sciences and Food Technology, Kebangsaan Universiti, Bangi, Selangor 43650, Malaysia
^*Correspondence e-mail: santhasrinithi@yahoo.co.in

(Received 18 June 2013; accepted 2 July 2013; online 10 July 2013)

In the title compound, C₁₅H₂₁ClN₂OS, the central chromophore moiety (C₂N₂OS) is approximately planar, with a maximum deviation of −0.027 (1) Å, and is oriented at a dihedral angle of 86.7 (1)° with respect to the chlorophenyl ring. An intramolecular N—H⋯O hydrogen bond stabilizes the molecular conformation. In the crystal, molecules associate via N—H⋯S hydrogen bonds, forming inversion dimers with motif R₂²(8). These dimers are further connected by N—H⋯O hydrogen bonds, forming R₂²(12) dimers. As a result, hydrogen-bonded chains running along [110] are formed. C—H⋯S interactions also occur. The terminal two C atoms of the butyl chain are disordered over two positions with an occupancy ratio of 0.54:0.46.

Related literature

For general background to the biological activity of thiourea derivatives, see: Yang et al. (2012 ); Wu et al. (2012 ); Abbas et al. (2013 ); Ryu et al. (2012 ).

Experimental

Crystal data

C₁₅H₂₁ClN₂OS
M_r = 312.85
Triclinic, $[P \overline 1]$
a = 7.264 (5) Å
b = 10.056 (7) Å
c = 11.935 (9) Å
α = 97.748 (17)°
β = 98.100 (17)°
γ = 103.72 (2)°
V = 825.5 (11) Å³
Z = 2
Mo Kα radiation
μ = 0.36 mm⁻¹
T = 292 K
0.22 × 0.20 × 0.18 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer
8136 measured reflections
2878 independent reflections
1700 reflections with I > 2σ(I)
R_int = 0.067

Refinement

R[F² > 2σ(F²)] = 0.076
wR(F²) = 0.230
S = 1.02
2878 reflections
200 parameters
4 restraints
H-atom parameters constrained
Δρ_max = 0.37 e Å⁻³
Δρ_min = −0.26 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1	0.86	1.98	2.652 (4)	134
N1—H1⋯O1ⁱ	0.86	2.49	3.184 (5)	139
N2—H2⋯S1ⁱⁱ	0.86	2.61	3.451 (4)	168
C9—H9⋯S1ⁱⁱ	0.98	2.81	3.725 (5)	157
Symmetry codes: (i) -x, -y+1, -z; (ii) -x+1, -y+2, -z.

Data collection: SMART (Bruker, 2001 ); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ) and PLATON (Spek, 2009 ); software used to prepare material for publication: SHELXL97 and PLATON.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053681301828X/bt6917sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053681301828X/bt6917Isup2.hkl

Supporting information file. DOI: 10.1107/S160053681301828X/bt6917Isup3.cml

checkCIF report

Comment top

Thiourea derivatives are an important class of organic compounds in which sulfur is the major ligand atom which plays an important role in coordination chemistry. Thiourea derivatives possess a wide range of biological activities such as antibacterial (Yang et al., 2012), antifungal (Wu et al., 2012; Abbas et al., 2013) activities. These derivatives sensitizes human H1299 lung carcinoma cells (Ryu et al., 2012). In view of the biological importance of thioureas, we have undertaken a single-crystal X-ray diffraction study of the title compound, and the results are presented here.

The molecular structure and atomic connectivity for the title compound are illustrated in Fig. 1. The central chromophore moiety (C₂N₂OS) is planar with a maximum deviation of -0.027 (1) Å for atom C8. The dihedral angle between the chlorophenyl ring and the chromophor moiety is 86.7 (1)°.

The molecular structure is stabilized by an intramolecular N—H···O hydrogen bond (Table 1). In the molecular packing, N—H···S hydrogen bonds involving atoms N2 and S1 link inversion-related molecules to form R₂²(8) graph set dimer (Fig. 2). These dimers are further connected by N—H···O hydrogen bonds forming R₂²(12) dimers (Fig. 3). As a result of that, hydrogen bonded chains running along [110] are formed.

Related literature top

For general background to the biological activity of thiourea derivatives, see: Yang et al. (2012); Wu et al. (2012); Abbas et al. (2013); Ryu et al. (2012).

Experimental top

A mixture of supersaturated solutions of 2-chlorophenol (1 mmol), thiourea (1 mmol) and 2-ethylhexanoic acid (1mmol) were dissolved in ethanol (20ml). The mixture was stirred well and refluxed to 3hours. The reaction was ensured with a yellow crystalline solid deposited at the bottom of the beaker. Single crystals of (I) were obtained by slow evaporation method using ethanol as solvent at at room temperature.

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of the title compound, showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level. The minor occupied atoms of the disordered part have been omitted for clarity.
	Fig. 2. Molecular packing of the title compound, viewed along the b axis; H-bonds are shown as dashed lines. For the sake of clarity, H atoms, not involved in hydrogen bonds, have been omitted. The minor occupied atoms of the disordered part have been omitted for clarity.
	Fig. 3. Molecular packing of the title compound, viewed down the a axis; H-bonds are shown as dashed lines. For the sake of clarity, H atoms, not involved in hydrogen bonds, have been omitted. Minor component of the disorder have been omitted for clarity.

1-(2-Chlorophenyl)-3-(2-ethylhexanoyl)thiourea top

Crystal data top

C₁₅H₂₁ClN₂OS	Z = 2
M_r = 312.85	F(000) = 332
Triclinic, P1	D_x = 1.259 Mg m⁻³
a = 7.264 (5) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.056 (7) Å	Cell parameters from 6222 reflections
c = 11.935 (9) Å	θ = 2.3–24.8°
α = 97.748 (17)°	µ = 0.36 mm⁻¹
β = 98.100 (17)°	T = 292 K
γ = 103.72 (2)°	Block, colourless
V = 825.5 (11) Å³	0.22 × 0.20 × 0.18 mm

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	R_int = 0.067
Radiation source: fine-focus sealed tube	θ_max = 25.0°, θ_min = 1.8°
ω scans	h = −8→8
8136 measured reflections	k = −11→11
2878 independent reflections	l = −14→14
1700 reflections with I > 2σ(I)

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)] = 0.076	H-atom parameters constrained
wR(F²) = 0.230	w = 1/[σ²(F_o²) + (0.125P)²] where P = (F_o² + 2F_c²)/3
S = 1.02	(Δ/σ)_max < 0.001
2878 reflections	Δρ_max = 0.37 e Å⁻³
200 parameters	Δρ_min = −0.26 e Å⁻³
4 restraints

Crystal data top

C₁₅H₂₁ClN₂OS	γ = 103.72 (2)°
M_r = 312.85	V = 825.5 (11) Å³
Triclinic, P1	Z = 2
a = 7.264 (5) Å	Mo Kα radiation
b = 10.056 (7) Å	µ = 0.36 mm⁻¹
c = 11.935 (9) Å	T = 292 K
α = 97.748 (17)°	0.22 × 0.20 × 0.18 mm
β = 98.100 (17)°

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	1700 reflections with I > 2σ(I)
8136 measured reflections	R_int = 0.067
2878 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.076	4 restraints
wR(F²) = 0.230	H-atom parameters constrained
S = 1.02	Δρ_max = 0.37 e Å⁻³
2878 reflections	Δρ_min = −0.26 e Å⁻³
200 parameters

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.

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
Cl1	0.0875 (2)	0.56892 (16)	−0.31845 (12)	0.0787 (5)
S1	0.23733 (18)	0.95432 (13)	−0.12264 (10)	0.0649 (5)
O1	0.1744 (4)	0.6032 (3)	0.0822 (3)	0.0589 (9)
N1	0.0376 (5)	0.7093 (4)	−0.0934 (3)	0.0478 (9)
H1	0.0249	0.6407	−0.0566	0.057*
N2	0.3169 (5)	0.8104 (4)	0.0374 (3)	0.0480 (9)
H2	0.4181	0.8790	0.0578	0.058*
C1	−0.2560 (7)	0.7626 (5)	−0.1733 (4)	0.0581 (12)
H1A	−0.2591	0.8089	−0.1010	0.070*
C2	−0.4017 (7)	0.7532 (6)	−0.2651 (5)	0.0677 (15)
H2A	−0.5034	0.7921	−0.2547	0.081*
C3	−0.3938 (8)	0.6860 (6)	−0.3712 (5)	0.0733 (16)
H3	−0.4911	0.6795	−0.4329	0.088*
C4	−0.2470 (8)	0.6287 (5)	−0.3879 (4)	0.0645 (14)
H4	−0.2441	0.5826	−0.4604	0.077*
C5	−0.1014 (6)	0.6392 (5)	−0.2968 (4)	0.0514 (12)
C6	−0.1079 (6)	0.7039 (4)	−0.1892 (3)	0.0425 (10)
C7	0.1916 (6)	0.8164 (4)	−0.0593 (3)	0.0455 (11)
C8	0.3017 (6)	0.7097 (5)	0.1054 (3)	0.0454 (10)
C9	0.4490 (7)	0.7445 (5)	0.2141 (4)	0.0563 (13)
H9	0.5358	0.8356	0.2147	0.068*
C10	0.5689 (8)	0.6399 (6)	0.2138 (4)	0.0719 (15)
H10A	0.6536	0.6587	0.2878	0.086*
H10B	0.4831	0.5478	0.2056	0.086*
C11	0.6883 (9)	0.6393 (7)	0.1219 (5)	0.094 (2)
H11A	0.6062	0.6196	0.0480	0.142*
H11B	0.7572	0.5693	0.1274	0.142*
H11C	0.7783	0.7287	0.1312	0.142*
C12	0.3511 (8)	0.7576 (6)	0.3165 (4)	0.0711 (15)
H12A	0.2709	0.6665	0.3194	0.085*
H12B	0.4495	0.7845	0.3853	0.085*
C13	0.2284 (12)	0.8584 (8)	0.3208 (5)	0.110 (2)
H13A	0.1449	0.8468	0.2473	0.132*	0.46
H13B	0.3081	0.9534	0.3400	0.132*	0.46
H13C	0.1402	0.8344	0.2478	0.132*	0.54
H13D	0.3138	0.9487	0.3212	0.132*	0.54
C14	0.104 (3)	0.8234 (19)	0.4181 (15)	0.109 (8)	0.46
H14A	−0.0231	0.8385	0.4033	0.131*	0.46
H14B	0.0991	0.7324	0.4382	0.131*	0.46
C15	0.251 (4)	0.941 (2)	0.499 (3)	0.187 (13)	0.46
H15A	0.2142	0.9492	0.5737	0.280*	0.46
H15B	0.2567	1.0259	0.4705	0.280*	0.46
H15C	0.3751	0.9218	0.5057	0.280*	0.46
C14'	0.105 (3)	0.882 (2)	0.4141 (13)	0.174 (14)	0.54
H14C	0.0756	0.9708	0.4128	0.209*	0.54
H14D	−0.0164	0.8103	0.3945	0.209*	0.54
C15'	0.197 (3)	0.879 (2)	0.5325 (13)	0.141 (10)	0.54
H15D	0.1141	0.8968	0.5853	0.211*	0.54
H15E	0.3176	0.9491	0.5529	0.211*	0.54
H15F	0.2200	0.7893	0.5360	0.211*	0.54

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0737 (10)	0.0888 (11)	0.0753 (9)	0.0267 (8)	0.0178 (7)	0.0058 (8)
S1	0.0619 (8)	0.0570 (8)	0.0629 (8)	−0.0092 (6)	−0.0105 (6)	0.0332 (6)
O1	0.056 (2)	0.054 (2)	0.0582 (19)	−0.0049 (17)	−0.0026 (15)	0.0277 (16)
N1	0.048 (2)	0.047 (2)	0.0413 (19)	−0.0009 (18)	−0.0026 (16)	0.0199 (17)
N2	0.046 (2)	0.047 (2)	0.0398 (19)	−0.0049 (16)	−0.0046 (15)	0.0137 (16)
C1	0.055 (3)	0.061 (3)	0.057 (3)	0.010 (2)	0.007 (2)	0.015 (2)
C2	0.045 (3)	0.066 (3)	0.093 (4)	0.012 (3)	0.004 (3)	0.029 (3)
C3	0.065 (4)	0.081 (4)	0.067 (4)	0.010 (3)	−0.014 (3)	0.030 (3)
C4	0.073 (4)	0.066 (3)	0.044 (3)	0.003 (3)	−0.005 (2)	0.014 (2)
C5	0.043 (3)	0.057 (3)	0.051 (3)	0.003 (2)	0.004 (2)	0.022 (2)
C6	0.035 (2)	0.045 (2)	0.042 (2)	−0.0019 (19)	−0.0005 (18)	0.016 (2)
C7	0.044 (2)	0.050 (3)	0.035 (2)	0.000 (2)	0.0018 (18)	0.010 (2)
C8	0.044 (2)	0.051 (3)	0.042 (2)	0.007 (2)	0.0069 (19)	0.018 (2)
C9	0.057 (3)	0.062 (3)	0.046 (3)	0.003 (2)	−0.003 (2)	0.028 (2)
C10	0.068 (4)	0.083 (4)	0.063 (3)	0.023 (3)	−0.008 (3)	0.023 (3)
C11	0.086 (4)	0.123 (6)	0.089 (4)	0.045 (4)	0.018 (4)	0.033 (4)
C12	0.090 (4)	0.069 (3)	0.046 (3)	0.006 (3)	0.004 (3)	0.014 (3)
C13	0.161 (7)	0.129 (6)	0.063 (4)	0.081 (6)	0.025 (4)	0.017 (4)
C14	0.113 (14)	0.079 (15)	0.15 (2)	0.065 (12)	0.018 (12)	−0.013 (12)
C15	0.14 (2)	0.12 (2)	0.27 (4)	0.027 (16)	−0.07 (2)	0.04 (2)
C14'	0.27 (3)	0.13 (2)	0.144 (18)	0.16 (2)	−0.006 (17)	−0.049 (15)
C15'	0.27 (3)	0.143 (17)	0.089 (11)	0.130 (19)	0.113 (15)	0.073 (12)

Geometric parameters (Å, º) top

Cl1—C5	1.720 (5)	C10—H10B	0.9700
S1—C7	1.655 (4)	C11—H11A	0.9600
O1—C8	1.206 (5)	C11—H11B	0.9600
N1—C7	1.326 (5)	C11—H11C	0.9600
N1—C6	1.430 (5)	C12—C13	1.501 (8)
N1—H1	0.8600	C12—H12A	0.9700
N2—C8	1.374 (5)	C12—H12B	0.9700
N2—C7	1.384 (5)	C13—C14'	1.553 (10)
N2—H2	0.8600	C13—C14	1.592 (10)
C1—C6	1.367 (6)	C13—H13A	0.9700
C1—C2	1.388 (7)	C13—H13B	0.9700
C1—H1A	0.9300	C13—H13C	0.9700
C2—C3	1.367 (7)	C13—H13D	0.9700
C2—H2A	0.9300	C14—C15	1.507 (10)
C3—C4	1.352 (7)	C14—H14A	0.9700
C3—H3	0.9300	C14—H14B	0.9700
C4—C5	1.379 (6)	C15—H15A	0.9600
C4—H4	0.9300	C15—H15B	0.9600
C5—C6	1.372 (6)	C15—H15C	0.9600
C8—C9	1.503 (6)	C14'—C15'	1.484 (10)
C9—C12	1.505 (7)	C14'—H14C	0.9700
C9—C10	1.516 (7)	C14'—H14D	0.9700
C9—H9	0.9800	C15'—H15D	0.9600
C10—C11	1.492 (8)	C15'—H15E	0.9600
C10—H10A	0.9700	C15'—H15F	0.9600

C7—N1—C6	122.2 (3)	C10—C11—H11C	109.5
C7—N1—H1	118.9	H11A—C11—H11C	109.5
C6—N1—H1	118.9	H11B—C11—H11C	109.5
C8—N2—C7	128.9 (4)	C13—C12—C9	116.9 (4)
C8—N2—H2	115.6	C13—C12—H12A	108.1
C7—N2—H2	115.6	C9—C12—H12A	108.1
C6—C1—C2	120.0 (5)	C13—C12—H12B	108.1
C6—C1—H1A	120.0	C9—C12—H12B	108.1
C2—C1—H1A	120.0	H12A—C12—H12B	107.3
C3—C2—C1	119.2 (5)	C12—C13—C14'	125.5 (8)
C3—C2—H2A	120.4	C12—C13—C14	105.6 (9)
C1—C2—H2A	120.4	C12—C13—H13A	110.6
C4—C3—C2	121.1 (5)	C14—C13—H13A	110.6
C4—C3—H3	119.4	C12—C13—H13B	110.6
C2—C3—H3	119.4	C14—C13—H13B	110.6
C3—C4—C5	119.6 (5)	H13A—C13—H13B	108.7
C3—C4—H4	120.2	C12—C13—H13C	105.9
C5—C4—H4	120.2	C14'—C13—H13C	105.9
C6—C5—C4	120.3 (5)	C12—C13—H13D	105.9
C6—C5—Cl1	120.0 (3)	C14'—C13—H13D	105.9
C4—C5—Cl1	119.7 (4)	H13C—C13—H13D	106.3
C1—C6—C5	119.7 (4)	C15—C14—C13	87.7 (19)
C1—C6—N1	119.8 (4)	C15—C14—H14A	114.0
C5—C6—N1	120.6 (4)	C13—C14—H14A	114.0
N1—C7—N2	116.1 (3)	C15—C14—H14B	114.0
N1—C7—S1	124.4 (3)	C13—C14—H14B	114.0
N2—C7—S1	119.5 (3)	H14A—C14—H14B	111.2
O1—C8—N2	122.6 (4)	C14—C15—H15A	109.5
O1—C8—C9	122.1 (4)	C14—C15—H15B	109.5
N2—C8—C9	115.3 (4)	H15A—C15—H15B	109.5
C8—C9—C12	109.7 (4)	C14—C15—H15C	109.5
C8—C9—C10	110.0 (4)	H15A—C15—H15C	109.5
C12—C9—C10	114.5 (4)	H15B—C15—H15C	109.5
C8—C9—H9	107.5	C15'—C14'—C13	114.4 (11)
C12—C9—H9	107.5	C15'—C14'—H14C	108.7
C10—C9—H9	107.5	C13—C14'—H14C	108.7
C11—C10—C9	115.2 (4)	C15'—C14'—H14D	108.7
C11—C10—H10A	108.5	C13—C14'—H14D	108.7
C9—C10—H10A	108.5	H14C—C14'—H14D	107.6
C11—C10—H10B	108.5	C14'—C15'—H15D	109.5
C9—C10—H10B	108.5	C14'—C15'—H15E	109.5
H10A—C10—H10B	107.5	H15D—C15'—H15E	109.5
C10—C11—H11A	109.5	C14'—C15'—H15F	109.5
C10—C11—H11B	109.5	H15D—C15'—H15F	109.5
H11A—C11—H11B	109.5	H15E—C15'—H15F	109.5

C6—C1—C2—C3	−0.7 (7)	C7—N2—C8—O1	5.4 (7)
C1—C2—C3—C4	0.0 (8)	C7—N2—C8—C9	−171.6 (4)
C2—C3—C4—C5	−0.6 (8)	O1—C8—C9—C12	−62.7 (6)
C3—C4—C5—C6	1.7 (7)	N2—C8—C9—C12	114.3 (4)
C3—C4—C5—Cl1	−178.9 (4)	O1—C8—C9—C10	64.0 (6)
C2—C1—C6—C5	1.8 (7)	N2—C8—C9—C10	−119.0 (4)
C2—C1—C6—N1	−177.5 (4)	C8—C9—C10—C11	64.0 (6)
C4—C5—C6—C1	−2.3 (7)	C12—C9—C10—C11	−172.0 (5)
Cl1—C5—C6—C1	178.3 (3)	C8—C9—C12—C13	−55.1 (6)
C4—C5—C6—N1	177.0 (4)	C10—C9—C12—C13	−179.3 (5)
Cl1—C5—C6—N1	−2.4 (6)	C9—C12—C13—C14'	176.0 (12)
C7—N1—C6—C1	−86.5 (5)	C9—C12—C13—C14	166.2 (9)
C7—N1—C6—C5	94.1 (5)	C12—C13—C14—C15	97.6 (12)
C6—N1—C7—N2	177.5 (4)	C14'—C13—C14—C15	−60 (3)
C6—N1—C7—S1	−1.0 (6)	C12—C13—C14'—C15'	39 (2)
C8—N2—C7—N1	−1.8 (7)	C14—C13—C14'—C15'	66 (4)
C8—N2—C7—S1	176.8 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1	0.86	1.98	2.652 (4)	134
N1—H1···O1ⁱ	0.86	2.49	3.184 (5)	139
N2—H2···S1ⁱⁱ	0.86	2.61	3.451 (4)	168
C9—H9···S1ⁱⁱ	0.98	2.81	3.725 (5)	157

Symmetry codes: (i) −x, −y+1, −z; (ii) −x+1, −y+2, −z.

Experimental details

Crystal data
Chemical formula	C₁₅H₂₁ClN₂OS
M_r	312.85
Crystal system, space group	Triclinic, P1
Temperature (K)	292
a, b, c (Å)	7.264 (5), 10.056 (7), 11.935 (9)
α, β, γ (°)	97.748 (17), 98.100 (17), 103.72 (2)
V (Å³)	825.5 (11)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.36
Crystal size (mm)	0.22 × 0.20 × 0.18

Data collection
Diffractometer	Bruker SMART APEX CCD area-detector diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	8136, 2878, 1700
R_int	0.067
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.076, 0.230, 1.02
No. of reflections	2878
No. of parameters	200
No. of restraints	4
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.37, −0.26

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL2013 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 2012) and PLATON (Spek, 2009), SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1	0.86	1.98	2.652 (4)	134.2
N1—H1···O1ⁱ	0.86	2.49	3.184 (5)	138.5
N2—H2···S1ⁱⁱ	0.86	2.61	3.451 (4)	167.9
C9—H9···S1ⁱⁱ	0.98	2.81	3.725 (5)	156.6

Symmetry codes: (i) −x, −y+1, −z; (ii) −x+1, −y+2, −z.

References

Abbas, S. Y., El-Sharief, M. A., Basyouni, W. M., Fakhr, I. M. & El-Gammal, E. W. (2013). Eur. J. Med. Chem. 64, 111–120. Web of Science CrossRef CAS PubMed Google Scholar
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Volume 69| Part 8| August 2013| Page o1220

doi:10.1107/S160053681301828X

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