1-Furoyl-3-methyl-3-phenyl­thio­urea

Pérez, H.; Mascarenhas, Y.; Estévez-Hernández, O.; Santos Jr, S.; Duque, J.

doi:10.1107/S1600536807068687

organic compounds

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ISSN: 2056-9890

Volume 64| Part 2| February 2008| Page o513

doi:10.1107/S1600536807068687

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1-Furoyl-3-methyl-3-phenylthiourea

Hiram Pérez,^a ^* Yvonne Mascarenhas,^b Osvaldo Estévez-Hernández,^c Sauli Santos Jr ^d and Julio Duque ^c

^aDepartamento de Química Inorgánica, Facultad de Química, Universidad de la Habana, Habana 10400, Cuba, ^bInstituto de Física de São Carlos, Universidade de São Paulo, São Carlos, Brazil, ^cInstituto de Ciencia y Tecnología de Materiales, Universidad de la Habana, Habana 10400, Cuba, and ^dLaboratório de Física, Universidade Federal do Tocantins, CEP 77020-120, Palmas, Tocantins, Brazil
^*Correspondence e-mail: hperez@fq.uh.cu

(Received 19 December 2007; accepted 29 December 2007; online 25 January 2008)

The title compound, C₁₃H₁₂N₂O₂S, crystallizes with two independent molecules in the asymmetric unit. The two molecules differ in the conformation of the thiocarbonyl and carbonyl groups, and show the typical geometric parameters of substituted thiourea derivatives. The crystal structure is mainly stabilized by intermolecular N—H⋯O hydrogen bonding.

Related literature

For general background, see: Estévez-Hernández et al. (2007 ); Otazo et al. (2001 ). For related structures, see: Koch et al. (1995 ); Morales et al. (1997 ). For synthesis, see: Otazo et al. (2001).

Experimental

Crystal data

C₁₃H₁₂N₂O₂S
M_r = 260.31
Monoclinic, P 2₁ /c
a = 10.242 (1) Å
b = 13.525 (1) Å
c = 18.432 (2) Å
β = 96.115 (4)°
V = 2538.7 (4) Å³
Z = 8
Mo Kα radiation
μ = 0.25 mm⁻¹
T = 150 (2) K
0.12 × 0.08 × 0.06 mm

Data collection

Nonius KappaCCD diffractometer
Absorption correction: none
23939 measured reflections
4440 independent reflections
2828 reflections with I > 2σ(I)
R_int = 0.093

Refinement

R[F² > 2σ(F²)] = 0.046
wR(F²) = 0.117
S = 1.01
4440 reflections
327 parameters
H-atom parameters constrained
Δρ_max = 0.26 e Å⁻³
Δρ_min = −0.39 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O3ⁱ	0.88	2.54	3.331 (3)	149
N4—H4⋯O1ⁱⁱ	0.88	2.17	3.010 (2)	159
Symmetry codes: (i) $[-x, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: COLLECT (Nonius, 2000 ); cell refinement: HKL SCALEPACK (Otwinowski & Minor, 1997 ); data reduction: HKL DENZO (Otwinowski & Minor, 1997) and SCALEPACK; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536807068687/xu2395sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536807068687/xu2395Isup2.hkl

checkCIF report

Comment top

Substituted N-acylthioureas have been a subject of investigations, due to their ability to form stable metal complexes and as ionophores in potenciometric and amperometric sensors for Cd(II), Hg(II) and Pb(II) (Otazo et al., 2001; Estévez-Hernández et al., 2007). The title compound, (I) (Fig. 1), is another example of our newly synthesized furoylthiourea derivatives, which shows outstanding complexation properties.

The main bond lengths and angles are given in Table 1, and are within the ranges obtained for similar compounds (Koch et al., 1995; Morales et al., 1997). The C—S and C3—O1, C16—O3 bonds show typical double-bond character. However, the C—N bond lengths, C2—N1, C2—N2, C3—N2, and the corresponding lengths for the other molecule are shorter than the normal C—N single-bond length of about 1.48 Å. These results can be explained by the existence of resonance in this part of the molecule. The crystal structure is stabilized by intermolecular N2—H2···O3 and N4—H4···O1 hydrogen-bonds (Table 2) between asymmetric units (Fig. 2).

The dihedral angles of two independent molecules between the furan and benzene ring planes are 67.8 (1)° and 82.8 (1)°, respectively. In addition, the conformation with respect to the thiocarbonyl and carbonyl moieties is twisted, as reflected by the torsion angles O1—C3—N2—C2 and C3—N2—C2—N1 of 0.3 (4) and -66.0 (3)° for one molecule, and O3—C16—N4—C15 and C16—N4—C15—N3 of -21.2 (4) and 61.9 (3)° for the other one.

Related literature top

For general background, see: Estévez-Hernández et al. (2007); Otazo et al. (2001). For related structures, see: Koch et al. (1995); Morales et al. (1997). For synthesis, see: Otazo et al. (2001).

Experimental top

The title compound, (I), was synthesized according to a procedure described by Otazo et al. (2001), by converting furoyl chloride into furoyl isothiocyanate and then condensing with the appropriate amine. The resulting solid product was crystallized from a dichlorometane-methanol (1:1) mixture yielding X-ray quality single crystals (m.p. 374.5 K). Elemental analysis for C₁₃H₁₂N₂O₂S found: C 55.7, H 7.5, N 9.6, S 22.1%; calculated: C 56.34, H 7.43, N 9.4, S 21.5%.

Computing details top

Data collection: Collect (Nonius, 2000); cell refinement: HKL SCALEPACK (Otwinowski & Minor, 1997); data reduction: HKL DENZO and SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top

	Fig. 1. The molecular structure of title compound. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. Intermolecular interaction observed between asymmetric units. Hydrogen-bonding is indicated by a dashed line.

1-Furoyl-3-methyl-3-phenylthiourea top

Crystal data top

C₁₃H₁₂N₂O₂S	F(000) = 1088
M_r = 260.31	D_x = 1.362 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 17369 reflections
a = 10.242 (1) Å	θ = 2.9–26.0°
b = 13.525 (1) Å	µ = 0.25 mm⁻¹
c = 18.432 (2) Å	T = 150 K
β = 96.115 (4)°	Prism, colourless
V = 2538.7 (4) Å³	0.12 × 0.08 × 0.06 mm
Z = 8

Data collection top

Nonius KappaCCD diffractometer	R_int = 0.093
CCD scans	θ_max = 25.0°, θ_min = 3.2°
23939 measured reflections	h = −12→12
4440 independent reflections	k = −15→16
2828 reflections with I > 2σ(I)	l = −21→21

Refinement top

Refinement on F²	0 restraints
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.046	w = 1/[σ²(F_o²) + (0.0586P)² + 0.0231P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.117	(Δ/σ)_max = 0.004
S = 1.01	Δρ_max = 0.26 e Å⁻³
4440 reflections	Δρ_min = −0.39 e Å⁻³
327 parameters

Crystal data top

C₁₃H₁₂N₂O₂S	V = 2538.7 (4) Å³
M_r = 260.31	Z = 8
Monoclinic, P2₁/c	Mo Kα radiation
a = 10.242 (1) Å	µ = 0.25 mm⁻¹
b = 13.525 (1) Å	T = 150 K
c = 18.432 (2) Å	0.12 × 0.08 × 0.06 mm
β = 96.115 (4)°

Data collection top

Nonius KappaCCD diffractometer	2828 reflections with I > 2σ(I)
23939 measured reflections	R_int = 0.093
4440 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.046	0 restraints
wR(F²) = 0.117	H-atom parameters constrained
S = 1.01	Δρ_max = 0.26 e Å⁻³
4440 reflections	Δρ_min = −0.39 e Å⁻³
327 parameters

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

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

	x	y	z	U_iso*/U_eq
C1	0.2294 (3)	0.8708 (2)	0.23749 (18)	0.0532 (8)
H1A	0.2926	0.8939	0.2049	0.08*
H1B	0.2749	0.8593	0.2863	0.08*
H1C	0.1611	0.921	0.2403	0.08*
C14	0.2728 (3)	0.3832 (2)	0.26750 (17)	0.0560 (9)
H14A	0.3457	0.4205	0.2506	0.084*
H14B	0.2145	0.4285	0.2903	0.084*
H14C	0.2234	0.3502	0.2259	0.084*
C2	0.1449 (2)	0.76315 (19)	0.13688 (16)	0.0351 (7)
C15	0.3838 (2)	0.22823 (19)	0.29748 (14)	0.0339 (6)
C3	0.1874 (2)	0.58628 (18)	0.12911 (14)	0.0302 (6)
C16	0.3287 (2)	0.10391 (18)	0.38668 (14)	0.0309 (6)
C4	0.1288 (2)	0.49232 (18)	0.10477 (14)	0.0298 (6)
C17	0.3758 (2)	0.00693 (18)	0.41385 (14)	0.0302 (6)
C5	0.0051 (2)	0.4590 (2)	0.09248 (17)	0.0452 (8)
H5	−0.0726	0.4963	0.0957	0.054*
C18	0.4789 (2)	−0.04906 (19)	0.40147 (15)	0.0355 (7)
H18	0.547	−0.0316	0.3727	0.043*
C6	0.0122 (3)	0.3574 (2)	0.07366 (17)	0.0450 (8)
H6	−0.0592	0.3132	0.0626	0.054*
C19	0.4675 (2)	−0.13922 (19)	0.43928 (16)	0.0386 (7)
H19	0.5266	−0.1935	0.4413	0.046*
C7	0.1390 (3)	0.3370 (2)	0.07479 (15)	0.0398 (7)
H7	0.173	0.274	0.0637	0.048*
C20	0.3574 (3)	−0.13276 (19)	0.47157 (16)	0.0396 (7)
H20	0.3249	−0.1833	0.5006	0.047*
C8	0.1275 (2)	0.70935 (19)	0.26202 (15)	0.0341 (6)
C21	0.3303 (2)	0.33719 (18)	0.39653 (15)	0.0341 (6)
C9	0.2181 (2)	0.6730 (2)	0.31625 (16)	0.0389 (7)
H9	0.3079	0.6915	0.3179	0.047*
C22	0.4509 (3)	0.34928 (19)	0.43744 (17)	0.0437 (7)
H22	0.5303	0.3339	0.4175	0.052*
C10	0.1775 (3)	0.6096 (2)	0.36825 (16)	0.0463 (8)
H10	0.2396	0.5842	0.4056	0.056*
C23	0.4529 (4)	0.3848 (2)	0.5091 (2)	0.0604 (10)
H23	0.5343	0.393	0.5384	0.072*
C11	0.0467 (3)	0.5832 (2)	0.36605 (17)	0.0445 (7)
H11	0.0191	0.5394	0.4017	0.053*
C24	0.3370 (4)	0.4078 (2)	0.53737 (19)	0.0632 (10)
H24	0.3388	0.4324	0.5857	0.076*
C12	−0.0436 (3)	0.6203 (2)	0.31213 (18)	0.0451 (8)
H12	−0.1333	0.6017	0.3106	0.054*
C25	0.2198 (4)	0.3950 (2)	0.4957 (2)	0.0555 (9)
H25	0.1403	0.4111	0.5152	0.067*
C13	−0.0042 (2)	0.6846 (2)	0.26012 (16)	0.0415 (7)
H13	−0.0666	0.7113	0.2236	0.05*
C26	0.2157 (3)	0.3593 (2)	0.42587 (17)	0.0428 (7)
H26	0.1335	0.3498	0.3977	0.051*
O1	0.29958 (15)	0.59531 (12)	0.15853 (10)	0.0392 (5)
O3	0.21895 (15)	0.13554 (12)	0.39322 (10)	0.0390 (5)
O2	0.21429 (15)	0.41764 (12)	0.09384 (10)	0.0385 (5)
O4	0.29752 (15)	−0.04324 (13)	0.45720 (10)	0.0399 (5)
N1	0.16896 (19)	0.77824 (15)	0.20905 (13)	0.0362 (5)
N3	0.32476 (19)	0.30851 (16)	0.32120 (12)	0.0370 (6)
N2	0.10521 (19)	0.66592 (15)	0.11680 (12)	0.0352 (6)
H2	0.0251	0.6562	0.0957	0.042*
N4	0.41900 (18)	0.15394 (15)	0.35015 (12)	0.0324 (5)
H4	0.5026	0.139	0.36	0.039*
S1	0.16001 (7)	0.84691 (5)	0.07255 (4)	0.0453 (2)
S2	0.41662 (7)	0.21011 (6)	0.21239 (4)	0.0489 (2)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.068 (2)	0.0363 (18)	0.054 (2)	−0.0138 (14)	−0.0010 (16)	−0.0080 (15)
C14	0.077 (2)	0.052 (2)	0.039 (2)	0.0213 (16)	0.0060 (16)	0.0122 (16)
C2	0.0294 (13)	0.0317 (16)	0.044 (2)	0.0030 (11)	0.0016 (12)	0.0027 (14)
C15	0.0277 (13)	0.0402 (17)	0.0344 (17)	0.0004 (11)	0.0063 (11)	0.0031 (14)
C3	0.0323 (15)	0.0325 (16)	0.0268 (16)	0.0011 (11)	0.0080 (11)	−0.0008 (12)
C16	0.0300 (14)	0.0341 (16)	0.0286 (17)	−0.0020 (11)	0.0037 (11)	−0.0026 (12)
C4	0.0317 (14)	0.0283 (15)	0.0295 (16)	0.0059 (11)	0.0031 (11)	0.0014 (12)
C17	0.0274 (13)	0.0321 (15)	0.0308 (17)	−0.0074 (11)	0.0014 (11)	0.0004 (12)
C5	0.0313 (15)	0.0412 (18)	0.062 (2)	0.0021 (12)	0.0024 (13)	−0.0063 (16)
C18	0.0315 (14)	0.0323 (16)	0.0444 (18)	−0.0015 (12)	0.0122 (12)	0.0007 (14)
C6	0.0445 (17)	0.0326 (17)	0.056 (2)	−0.0088 (12)	−0.0020 (14)	−0.0038 (15)
C19	0.0378 (15)	0.0346 (17)	0.0436 (19)	0.0020 (12)	0.0062 (13)	−0.0012 (14)
C7	0.0495 (18)	0.0266 (16)	0.0420 (19)	−0.0019 (13)	−0.0013 (13)	−0.0048 (13)
C20	0.0490 (17)	0.0304 (16)	0.0389 (19)	−0.0007 (12)	0.0028 (13)	0.0062 (13)
C8	0.0402 (15)	0.0288 (15)	0.0334 (17)	−0.0011 (11)	0.0045 (12)	−0.0053 (13)
C21	0.0412 (15)	0.0284 (15)	0.0334 (18)	−0.0001 (11)	0.0070 (12)	0.0053 (13)
C9	0.0358 (15)	0.0438 (17)	0.0376 (18)	−0.0029 (12)	0.0066 (13)	−0.0033 (14)
C22	0.0453 (17)	0.0353 (17)	0.049 (2)	−0.0010 (13)	−0.0010 (14)	0.0050 (15)
C10	0.0451 (17)	0.053 (2)	0.041 (2)	0.0050 (14)	0.0053 (14)	0.0009 (16)
C23	0.084 (3)	0.0342 (19)	0.056 (3)	−0.0078 (16)	−0.0251 (19)	0.0051 (17)
C11	0.0477 (17)	0.0416 (18)	0.047 (2)	0.0020 (13)	0.0177 (14)	−0.0003 (15)
C24	0.123 (3)	0.0331 (19)	0.035 (2)	0.0044 (19)	0.012 (2)	0.0034 (15)
C12	0.0379 (16)	0.0438 (18)	0.055 (2)	−0.0028 (13)	0.0122 (14)	−0.0054 (16)
C25	0.081 (2)	0.0375 (19)	0.052 (2)	0.0048 (16)	0.0279 (19)	0.0048 (17)
C13	0.0358 (15)	0.0379 (17)	0.050 (2)	0.0019 (12)	0.0020 (13)	−0.0054 (15)
C26	0.0473 (16)	0.0383 (18)	0.045 (2)	0.0007 (13)	0.0127 (14)	0.0042 (15)
O1	0.0276 (10)	0.0407 (11)	0.0491 (13)	−0.0014 (8)	0.0033 (8)	−0.0089 (9)
O3	0.0271 (10)	0.0377 (11)	0.0534 (14)	0.0017 (8)	0.0096 (8)	0.0049 (9)
O2	0.0369 (10)	0.0320 (11)	0.0463 (13)	0.0014 (8)	0.0033 (8)	−0.0040 (9)
O4	0.0359 (10)	0.0405 (12)	0.0448 (13)	0.0017 (8)	0.0111 (8)	0.0081 (9)
N1	0.0414 (12)	0.0281 (13)	0.0381 (16)	−0.0031 (9)	−0.0002 (10)	−0.0016 (11)
N3	0.0417 (12)	0.0370 (14)	0.0327 (15)	0.0092 (10)	0.0060 (10)	0.0061 (11)
N2	0.0304 (11)	0.0299 (13)	0.0431 (15)	0.0005 (9)	−0.0060 (9)	−0.0039 (11)
N4	0.0249 (11)	0.0361 (13)	0.0367 (15)	0.0017 (9)	0.0051 (9)	0.0079 (11)
S1	0.0509 (4)	0.0379 (4)	0.0480 (5)	0.0009 (3)	0.0090 (3)	0.0061 (4)
S2	0.0498 (4)	0.0634 (6)	0.0351 (5)	0.0115 (4)	0.0115 (3)	0.0031 (4)

Geometric parameters (Å, º) top

C1—N1	1.468 (3)	C19—H19	0.95
C1—H1A	0.98	C7—O2	1.360 (3)
C1—H1B	0.98	C7—H7	0.95
C1—H1C	0.98	C20—O4	1.370 (3)
C14—N3	1.473 (3)	C20—H20	0.95
C14—H14A	0.98	C8—C9	1.380 (4)
C14—H14B	0.98	C8—C13	1.386 (3)
C14—H14C	0.98	C8—N1	1.446 (3)
C2—N1	1.342 (3)	C21—C26	1.376 (4)
C2—N2	1.414 (3)	C21—C22	1.387 (4)
C2—S1	1.659 (3)	C21—N3	1.437 (3)
C15—N3	1.339 (3)	C9—C10	1.383 (4)
C15—N4	1.417 (3)	C9—H9	0.95
C15—S2	1.657 (3)	C22—C23	1.404 (5)
C3—O1	1.223 (3)	C22—H22	0.95
C3—N2	1.371 (3)	C10—C11	1.383 (4)
C3—C4	1.456 (3)	C10—H10	0.95
C16—O3	1.221 (3)	C23—C24	1.381 (5)
C16—N4	1.378 (3)	C23—H23	0.95
C16—C17	1.467 (3)	C11—C12	1.378 (4)
C4—C5	1.341 (3)	C11—H11	0.95
C4—O2	1.366 (3)	C24—C25	1.365 (5)
C17—C18	1.338 (3)	C24—H24	0.95
C17—O4	1.371 (3)	C12—C13	1.386 (4)
C5—C6	1.421 (4)	C12—H12	0.95
C5—H5	0.95	C25—C26	1.371 (4)
C18—C19	1.416 (4)	C25—H25	0.95
C18—H18	0.95	C13—H13	0.95
C6—C7	1.326 (3)	C26—H26	0.95
C6—H6	0.95	N2—H2	0.88
C19—C20	1.333 (4)	N4—H4	0.88

N1—C1—H1A	109.5	C9—C8—N1	119.7 (2)
N1—C1—H1B	109.5	C13—C8—N1	119.6 (2)
H1A—C1—H1B	109.5	C26—C21—C22	120.5 (3)
N1—C1—H1C	109.5	C26—C21—N3	119.4 (2)
H1A—C1—H1C	109.5	C22—C21—N3	119.9 (2)
H1B—C1—H1C	109.5	C8—C9—C10	119.6 (2)
N3—C14—H14A	109.5	C8—C9—H9	120.2
N3—C14—H14B	109.5	C10—C9—H9	120.2
H14A—C14—H14B	109.5	C21—C22—C23	118.3 (3)
N3—C14—H14C	109.5	C21—C22—H22	120.8
H14A—C14—H14C	109.5	C23—C22—H22	120.8
H14B—C14—H14C	109.5	C9—C10—C11	120.1 (3)
N1—C2—N2	114.7 (2)	C9—C10—H10	119.9
N1—C2—S1	125.7 (2)	C11—C10—H10	119.9
N2—C2—S1	119.6 (2)	C24—C23—C22	120.3 (3)
N3—C15—N4	116.2 (2)	C24—C23—H23	119.8
N3—C15—S2	125.0 (2)	C22—C23—H23	119.8
N4—C15—S2	118.77 (19)	C12—C11—C10	120.0 (3)
O1—C3—N2	121.7 (2)	C12—C11—H11	120
O1—C3—C4	124.1 (2)	C10—C11—H11	120
N2—C3—C4	114.2 (2)	C25—C24—C23	119.9 (3)
O3—C16—N4	123.3 (2)	C25—C24—H24	120
O3—C16—C17	123.5 (2)	C23—C24—H24	120
N4—C16—C17	113.1 (2)	C11—C12—C13	120.3 (3)
C5—C4—O2	109.6 (2)	C11—C12—H12	119.9
C5—C4—C3	134.1 (2)	C13—C12—H12	119.9
O2—C4—C3	116.2 (2)	C24—C25—C26	120.7 (3)
C18—C17—O4	109.9 (2)	C24—C25—H25	119.7
C18—C17—C16	133.2 (2)	C26—C25—H25	119.7
O4—C17—C16	116.7 (2)	C12—C13—C8	119.3 (3)
C4—C5—C6	107.1 (2)	C12—C13—H13	120.4
C4—C5—H5	126.4	C8—C13—H13	120.4
C6—C5—H5	126.4	C25—C26—C21	120.2 (3)
C17—C18—C19	107.2 (2)	C25—C26—H26	119.9
C17—C18—H18	126.4	C21—C26—H26	119.9
C19—C18—H18	126.4	C7—O2—C4	106.06 (19)
C7—C6—C5	105.8 (2)	C20—O4—C17	105.79 (19)
C7—C6—H6	127.1	C2—N1—C8	122.3 (2)
C5—C6—H6	127.1	C2—N1—C1	120.6 (2)
C20—C19—C18	106.3 (2)	C8—N1—C1	116.8 (2)
C20—C19—H19	126.8	C15—N3—C21	124.2 (2)
C18—C19—H19	126.8	C15—N3—C14	118.7 (2)
C6—C7—O2	111.4 (2)	C21—N3—C14	116.0 (2)
C6—C7—H7	124.3	C3—N2—C2	122.2 (2)
O2—C7—H7	124.3	C3—N2—H2	118.9
C19—C20—O4	110.8 (2)	C2—N2—H2	118.9
C19—C20—H20	124.6	C16—N4—C15	123.24 (19)
O4—C20—H20	124.6	C16—N4—H4	118.4
C9—C8—C13	120.6 (3)	C15—N4—H4	118.4

O1—C3—C4—C5	156.2 (3)	N3—C21—C26—C25	−174.3 (2)
N2—C3—C4—C5	−23.3 (4)	C6—C7—O2—C4	−0.3 (3)
O1—C3—C4—O2	−20.7 (4)	C5—C4—O2—C7	−0.3 (3)
N2—C3—C4—O2	159.7 (2)	C3—C4—O2—C7	177.3 (2)
O3—C16—C17—C18	165.5 (3)	C19—C20—O4—C17	0.0 (3)
N4—C16—C17—C18	−11.8 (4)	C18—C17—O4—C20	0.4 (3)
O3—C16—C17—O4	−9.2 (4)	C16—C17—O4—C20	176.3 (2)
N4—C16—C17—O4	173.5 (2)	N2—C2—N1—C8	−14.4 (3)
O2—C4—C5—C6	0.8 (3)	S1—C2—N1—C8	166.46 (18)
C3—C4—C5—C6	−176.3 (3)	N2—C2—N1—C1	170.9 (2)
O4—C17—C18—C19	−0.7 (3)	S1—C2—N1—C1	−8.2 (3)
C16—C17—C18—C19	−175.7 (3)	C9—C8—N1—C2	126.6 (3)
C4—C5—C6—C7	−0.9 (3)	C13—C8—N1—C2	−56.9 (3)
C17—C18—C19—C20	0.7 (3)	C9—C8—N1—C1	−58.6 (3)
C5—C6—C7—O2	0.8 (3)	C13—C8—N1—C1	118.0 (3)
C18—C19—C20—O4	−0.4 (3)	N4—C15—N3—C21	19.3 (3)
C13—C8—C9—C10	1.4 (4)	S2—C15—N3—C21	−161.15 (19)
N1—C8—C9—C10	177.9 (2)	N4—C15—N3—C14	−173.3 (2)
C26—C21—C22—C23	−0.2 (4)	S2—C15—N3—C14	6.2 (3)
N3—C21—C22—C23	175.1 (2)	C26—C21—N3—C15	−129.9 (3)
C8—C9—C10—C11	−0.3 (4)	C22—C21—N3—C15	54.7 (3)
C21—C22—C23—C24	−0.7 (4)	C26—C21—N3—C14	62.4 (3)
C9—C10—C11—C12	−0.2 (4)	C22—C21—N3—C14	−112.9 (3)
C22—C23—C24—C25	0.7 (5)	O1—C3—N2—C2	0.3 (4)
C10—C11—C12—C13	−0.4 (4)	C4—C3—N2—C2	179.9 (2)
C23—C24—C25—C26	0.1 (5)	N1—C2—N2—C3	−66.0 (3)
C11—C12—C13—C8	1.4 (4)	S1—C2—N2—C3	113.1 (2)
C9—C8—C13—C12	−2.0 (4)	O3—C16—N4—C15	−21.2 (4)
N1—C8—C13—C12	−178.5 (2)	C17—C16—N4—C15	156.1 (2)
C24—C25—C26—C21	−1.0 (4)	N3—C15—N4—C16	61.9 (3)
C22—C21—C26—C25	1.0 (4)	S2—C15—N4—C16	−117.7 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O3ⁱ	0.88	2.54	3.331 (3)	149
N4—H4···O1ⁱⁱ	0.88	2.17	3.010 (2)	159
C5—H5···O3ⁱ	0.95	2.43	3.341 (3)	161
C5—H5···O4ⁱ	0.95	2.46	3.137 (3)	128
C14—H14C···O2	0.98	2.59	3.227 (4)	123
C18—H18···O1ⁱⁱ	0.95	2.44	3.274 (3)	147
C18—H18···O2ⁱⁱ	0.95	2.55	3.167 (3)	123

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

Experimental details

Crystal data
Chemical formula	C₁₃H₁₂N₂O₂S
M_r	260.31
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	150
a, b, c (Å)	10.242 (1), 13.525 (1), 18.432 (2)
β (°)	96.115 (4)
V (Å³)	2538.7 (4)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.25
Crystal size (mm)	0.12 × 0.08 × 0.06

Data collection
Diffractometer	Nonius KappaCCD diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	23939, 4440, 2828
R_int	0.093
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.046, 0.117, 1.01
No. of reflections	4440
No. of parameters	327
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.26, −0.39

Computer programs: Collect (Nonius, 2000), HKL SCALEPACK (Otwinowski & Minor, 1997), HKL DENZO and SCALEPACK (Otwinowski & Minor, 1997), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999).

Selected bond lengths (Å) top

C2—N1	1.342 (3)	C15—S2	1.657 (3)
C2—N2	1.414 (3)	C3—O1	1.223 (3)
C2—S1	1.659 (3)	C3—N2	1.371 (3)
C15—N3	1.339 (3)	C16—O3	1.221 (3)
C15—N4	1.417 (3)	C16—N4	1.378 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O3ⁱ	0.88	2.54	3.331 (3)	149.00
N4—H4···O1ⁱⁱ	0.88	2.17	3.010 (2)	159.00

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

Acknowledgements

The authors thank the Crystallography Group, São Carlos Physics Institute, USP, Brazil, for allowing X-ray data collection. The authors acknowledge financial support from the Brazilian agency CAPES (project 018/05).

References

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