1-Furoyl-3-[3-(trifluoro­meth­yl)phen­yl]thio­urea

Theodoro, J.E.; Estévez-Hernández, O.; Ellena, J.; Duque, J.; Corrêa, R.S.

doi:10.1107/S1600536809013038

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 65| Part 5| May 2009| Page o1012

doi:10.1107/S1600536809013038

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1-Furoyl-3-[3-(trifluoromethyl)phenyl]thiourea

Jahyr E. Theodoro,^a O. Estévez-Hernández,^b ^* J. Ellena,^a J. Duque ^b and Rodrigo S. Corrêa ^a

^aGrupo de Cristalografía, Instituto de Física de São Carlos, Universidade de São Paulo, São Carlos, Brazil, and ^bLaboratory of Molecular Ingeniery, Institute of Materials, University of Havana, Cuba
^*Correspondence e-mail: osvaldo@imre.oc.uh.cu

(Received 6 March 2009; accepted 6 April 2009; online 10 April 2009)

The title compound, C₁₃H₉F₃N₂O₂S, crystallizes with two independent molecules in the asymmetric unit. The central thiourea core is roughly coplanar with the furan and benzene rings, showing O—C—N—C(S) torsion angles of 2.3 (4) and −11.4 (2)° and (S)C—N—C—C torsion angles of −2.4 (4) and −28.8 (4)°, respectively, in the two independent molecules. The trans–cis geometry of the thiourea fragment is stabilized by an intramolecular N—H⋯O hydrogen bond between the H atom of the cis thioamide and the carbonyl O atom. In the crystal structure, intermolecular N—H⋯S hydrogen bonds form centrosymmetric dimers extending along the b axis.

Related literature

For general background to aroylthioureas, see: Aly et al. (2007 ); Koch (2001 ); Estévez-Hernández et al. (2007 ); Otazo-Sánchez et al. (2002 ). For related structures, see: Theodoro et al. (2008 ); Pérez et al. (2008 ). For the synthesis, see: Otazo-Sánchez et al. (2001 ).

Experimental

Crystal data

C₁₃H₉F₃N₂O₂S
M_r = 314.29
Triclinic, $[P \overline 1]$
a = 7.5540 (14) Å
b = 13.684 (5) Å
c = 14.210 (3) Å
α = 86.124 (13)°
β = 74.779 (7)°
γ = 74.065 (8)°
V = 1362.9 (6) Å³
Z = 4
Mo Kα radiation
μ = 0.28 mm⁻¹
T = 294 K
0.09 × 0.07 × 0.03 mm

Data collection

Enraf–Nonius KappaCCD diffractometer
Absorption correction: none
9271 measured reflections
4953 independent reflections
2925 reflections with I > 2σ(I)
R_int = 0.035

Refinement

R[F² > 2σ(F²)] = 0.044
wR(F²) = 0.123
S = 1.01
4953 reflections
433 parameters
H-atom parameters constrained
Δρ_max = 0.14 e Å⁻³
Δρ_min = −0.24 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯S1Aⁱ	0.86	2.78	3.643 (2)	176
N1—H1⋯O2	0.86	2.27	2.692 (3)	110
N1A—H1A⋯S1ⁱⁱ	0.86	2.74	3.592 (2)	173
N1A—H1A⋯O2A	0.86	2.30	2.700 (3)	108
N2—H2⋯O1	0.86	1.88	2.625 (3)	144
N2A—H2A⋯O1A	0.86	1.92	2.640 (3)	140
Symmetry codes: (i) x, y-1, z; (ii) x, y+1, z.

Data collection: COLLECT (Nonius, 2000 ); cell refinement: SCALEPACK (Otwinowski & Minor, 1997 ); data reduction: 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 ) and Mercury (Macrae et al., 2006 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809013038/fj2202sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809013038/fj2202Isup2.hkl

checkCIF report

Comment top

The importance of aroylthioureas is found largely in heterocyclic syntheses and many of these substrates have interesting biological activities. Aroylthioureas have also been found to have applications in metal complexes and molecular electronics (Aly et al., 2007). The title compound (I), Fig. 1, was synthesized from furoyl isothiocyanate and 3-trifluorometylaniline in dry acetone. This thiourea derivative has been successfully used as ionophore in amperometric sensor for Cd(II) (Estévez-Hernández et al., 2007). The title compound crystallizes in the thioamide form with two independent molecules in the asymmetric unit. The main bond lengths are within the ranges obtained for similar compounds (Koch et al., 2001 and Pérez et al., 2008). The C2—S1 and C1—O1 bonds (Table 1) both show the expected double-bond character. The short values of the C2—N1, C2—N2 and C1—N2 bonds indicate partial double bond character. These results can be explained by the existence of resonance in this part of the molecule. The C=S distance for compound I (two unique molecules) averages 1.648 Å. The furan carbonyl (O1—C1—C3—O2 and O1a—C1a—C3a—O2a, two unique molecules) groups are inclined 2.3 (4)° and -11.4 (2)° with respect to the plane formed by the thiourea moiety (N1—C2—S1—N2 and N1a—C2a—S2—N2a, two unique molecules)in each molecule, while the 3-trifluoromethylphenyl (C7—C8—C9—C10—C11 and C7a—C8a—C9a—C10a—C11a, two unique molecules) rings are inclined -2.4 (4)° and -28.8 (4)°, respectively. In addition, the dihedral angles of two independent molecules between the furan and benzene ring planes are 18.91 (1)° and 14.78 (1)°, respectively. The trans-cis geometry in the thiourea moiety is stabilized by the N2—H2···.O1 intramolecular hydrogen bond. This strong interaction is also observed in solution (Otazo-Sánchez et al., 2002) and locks the –CONHCSNHR– unit into a stable planar six-membered ring structure (Fig.1 and Table 1). In this S-shaped conformation between the C=O and C=S groups (two donors sites rich in electron density), the O—S distance is maximum, contributing to a minimum conformational energy of the molecule as a whole (Koch et al., 2001). Another weaker intramolecular hydrogen interaction between the furan oxygen atom O2 and the N1—H1 hydrogen atom is observed. The crystal structure is stabilized by two intermolecular N1—H1···.S1 hydrogen bonds (Fig.2 and Table 1) between related molecules forming dimers pilled within the unit cell along the [010] direction.

Related literature top

For general background to aroylthioureas, see: Aly et al. (2007); Koch (2001); Estévez-Hernández et al. (2007); Otazo-Sánchez et al. (2002). For related structures, see: Theodoro et al. (2008); Pérez et al. (2008). For the synthesis, see: Otazo-Sánchez et al. (2001).

Experimental top

The title compound (I) was synthesized according to a previous report (Otazo-Sánchez et al., 2001), by converting furoyl chloride into furoyl isothiocyanate and then condensing with 3-trifluorometylaniline. The resulting solid product was crystallized from ethanol yielding X-ray quality single crystals (m.p 112–113 °C). Elemental analysis (%) for C₁₃H₉N₂O₂F₃S calculated: C 49.68, H 2.87, N 8.92, S 10.19; found: C 49.46, H 2.86, N 15.79, S 10.09.

Computing details top

Data collection: COLLECT (Nonius, 2000); cell refinement: SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO and SCALEPACK (Otwinowski & Minor, 1997); 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) and Mercury (Macrae et al., 2006); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top

	Fig. 1. The molecular structure of the title compound. Displacement ellipsoids are drawn at the 50% probability level. The intramolecular N—H···O hydrogen bond is shown as a dashed line. For clarity reason the atoms (C13, C13a, F1, F1a, F2, F2a, F3 and F3a) of the trifluoromethyl groups are not labeled.
	Fig. 2. View of the crystal packing of the title compound. Intermolecular hydrogen bonds are shown as dashed lines.

1-Furoyl-3-[3-(trifluoromethyl)phenyl]thiourea top

Crystal data top

C₁₃H₉F₃N₂O₂S	Z = 4
M_r = 314.29	F(000) = 640
Triclinic, P1	D_x = 1.532 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.5540 (14) Å	Cell parameters from 8001 reflections
b = 13.684 (5) Å	θ = 2.9–26.7°
c = 14.210 (3) Å	µ = 0.28 mm⁻¹
α = 86.124 (13)°	T = 294 K
β = 74.779 (7)°	Prism, colourless
γ = 74.065 (8)°	0.09 × 0.07 × 0.03 mm
V = 1362.9 (6) Å³

Data collection top

Enraf–Nonius KappaCCD diffractometer	2925 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube Enraf Nonius FR590	R_int = 0.035
Horizontally mounted graphite crystal monochromator	θ_max = 25.4°, θ_min = 2.9°
ϕ scans and ω scans winth κ offsets	h = −9→9
9271 measured reflections	k = −16→16
4953 independent reflections	l = −17→17

Refinement top

Refinement on F²	0 restraints
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.044	w = 1/[σ²(F_o²) + (0.058P)² + 0.0881P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.123	(Δ/σ)_max < 0.001
S = 1.01	Δρ_max = 0.14 e Å⁻³
4953 reflections	Δρ_min = −0.24 e Å⁻³
433 parameters

Crystal data top

C₁₃H₉F₃N₂O₂S	γ = 74.065 (8)°
M_r = 314.29	V = 1362.9 (6) Å³
Triclinic, P1	Z = 4
a = 7.5540 (14) Å	Mo Kα radiation
b = 13.684 (5) Å	µ = 0.28 mm⁻¹
c = 14.210 (3) Å	T = 294 K
α = 86.124 (13)°	0.09 × 0.07 × 0.03 mm
β = 74.779 (7)°

Data collection top

Enraf–Nonius KappaCCD diffractometer	2925 reflections with I > 2σ(I)
9271 measured reflections	R_int = 0.035
4953 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.044	0 restraints
wR(F²) = 0.123	H-atom parameters constrained
S = 1.01	Δρ_max = 0.14 e Å⁻³
4953 reflections	Δρ_min = −0.24 e Å⁻³
433 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	Occ. (<1)
C1	0.3542 (4)	0.0592 (2)	0.38462 (18)	0.0710 (7)
C2	0.1946 (3)	0.02259 (17)	0.55546 (17)	0.0645 (6)
C3	0.4502 (4)	0.01038 (19)	0.29077 (17)	0.0710 (7)
C4	0.5248 (4)	0.0463 (2)	0.2042 (2)	0.0936 (9)
H4	0.5281	0.1131	0.1895	0.112*
C5	0.5978 (5)	−0.0373 (3)	0.1393 (2)	0.1019 (10)
H5	0.6575	−0.036	0.0733	0.122*
C6	0.5654 (5)	−0.1173 (3)	0.1899 (2)	0.1062 (10)
H6	0.5997	−0.1828	0.1647	0.127*
C7	0.0783 (3)	0.17521 (17)	0.66537 (17)	0.0655 (6)
C8	−0.0076 (4)	0.13680 (18)	0.75310 (17)	0.0712 (6)
H8	−0.0151	0.0699	0.7569	0.085*
C9	−0.0816 (4)	0.19813 (18)	0.83429 (18)	0.0707 (6)
C10	−0.0735 (4)	0.2979 (2)	0.8295 (2)	0.0869 (8)
H10	−0.1238	0.339	0.8849	0.104*
C11	0.0087 (4)	0.3353 (2)	0.7432 (2)	0.0930 (9)
H11	0.0132	0.4028	0.7395	0.112*
C12	0.0852 (4)	0.27506 (19)	0.6615 (2)	0.0782 (7)
H12	0.1422	0.3017	0.6031	0.094*
C13	−0.1660 (6)	0.1558 (3)	0.9296 (2)	0.0923 (9)
O1	0.3279 (3)	0.15065 (15)	0.39493 (13)	0.0941 (6)
O2	0.4751 (3)	−0.09106 (15)	0.28394 (13)	0.0929 (6)
N1	0.2953 (3)	−0.00303 (14)	0.45947 (13)	0.0678 (5)
H1	0.3248	−0.0665	0.445	0.081*
N2	0.1654 (3)	0.11989 (15)	0.57768 (15)	0.0745 (6)
H2	0.2079	0.1556	0.5293	0.089*
S1	0.12519 (11)	−0.06681 (5)	0.62741 (5)	0.0817 (2)
F2	−0.3379 (18)	0.2058 (8)	0.9735 (10)	0.145 (5)	0.6
F1	−0.0713 (15)	0.1517 (11)	0.9950 (9)	0.138 (4)	0.6
F3	−0.1806 (18)	0.0624 (6)	0.9246 (6)	0.135 (4)	0.6
F11	−0.121 (4)	0.1867 (19)	1.0000 (13)	0.206 (11)	0.4
F21	−0.356 (3)	0.1899 (16)	0.9474 (15)	0.158 (8)	0.4
F31	−0.125 (3)	0.0578 (8)	0.9282 (11)	0.161 (7)	0.4
C1A	0.0472 (3)	0.6271 (2)	0.62271 (17)	0.0678 (6)
C2A	0.2779 (3)	0.65003 (18)	0.46698 (16)	0.0631 (6)
C3A	−0.0434 (3)	0.67263 (18)	0.71851 (17)	0.0677 (6)
C4A	−0.1499 (4)	0.6405 (2)	0.79957 (19)	0.0834 (8)
H4A	−0.1881	0.5808	0.8067	0.1*
C5A	−0.1920 (4)	0.7148 (2)	0.8713 (2)	0.0939 (9)
H5A	−0.2637	0.7136	0.9353	0.113*
C6A	−0.1105 (4)	0.7871 (2)	0.8307 (2)	0.0924 (9)
H6A	−0.1161	0.8454	0.8626	0.111*
C7A	0.4030 (3)	0.49953 (18)	0.35601 (16)	0.0629 (6)
C8A	0.4819 (3)	0.54077 (18)	0.26840 (17)	0.0693 (6)
H8A	0.4581	0.6109	0.2612	0.083*
C9A	0.5957 (3)	0.47733 (19)	0.19206 (17)	0.0673 (6)
C10A	0.6284 (4)	0.3734 (2)	0.2009 (2)	0.0793 (7)
H10A	0.7044	0.3309	0.149	0.095*
C11A	0.5474 (4)	0.3332 (2)	0.2875 (2)	0.0841 (8)
H11A	0.5688	0.2632	0.2941	0.101*
C12A	0.4355 (4)	0.39553 (18)	0.36399 (19)	0.0724 (7)
H12A	0.3807	0.3674	0.422	0.087*
C13A	0.6833 (5)	0.5235 (3)	0.1000 (2)	0.0856 (8)
O1A	0.0331 (3)	0.54417 (14)	0.60375 (13)	0.0879 (6)
O2A	−0.0178 (2)	0.76400 (13)	0.73597 (12)	0.0789 (5)
N1A	0.1507 (3)	0.68170 (14)	0.55649 (13)	0.0672 (5)
H1A	0.1345	0.7436	0.5726	0.081*
N2A	0.2842 (3)	0.55799 (14)	0.43803 (13)	0.0693 (5)
H2A	0.2028	0.5299	0.4754	0.083*
S1A	0.40615 (12)	0.72621 (6)	0.40944 (5)	0.0884 (3)
F2A	0.5546 (12)	0.5748 (9)	0.0533 (6)	0.136 (3)	0.6
F3A	0.7983 (13)	0.4580 (9)	0.0347 (7)	0.137 (5)	0.6
F1A	0.7723 (19)	0.5875 (10)	0.1111 (4)	0.138 (4)	0.6
F2B	0.594 (3)	0.6154 (10)	0.0881 (10)	0.157 (6)	0.4
F1B	0.8549 (18)	0.5299 (15)	0.1025 (12)	0.171 (8)	0.4
F3B	0.710 (4)	0.4729 (16)	0.0251 (10)	0.193 (9)	0.4

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0753 (17)	0.0767 (17)	0.0623 (16)	−0.0278 (13)	−0.0144 (13)	0.0109 (13)
C2	0.0713 (15)	0.0653 (15)	0.0570 (14)	−0.0215 (12)	−0.0131 (12)	0.0013 (11)
C3	0.0786 (17)	0.0744 (17)	0.0596 (15)	−0.0261 (13)	−0.0130 (13)	0.0086 (12)
C4	0.103 (2)	0.098 (2)	0.0745 (19)	−0.0383 (17)	−0.0082 (16)	0.0213 (17)
C5	0.107 (2)	0.133 (3)	0.0561 (17)	−0.032 (2)	−0.0066 (16)	0.0116 (19)
C6	0.128 (3)	0.109 (2)	0.0667 (19)	−0.027 (2)	−0.0025 (18)	−0.0139 (18)
C7	0.0716 (16)	0.0600 (14)	0.0641 (15)	−0.0196 (12)	−0.0131 (12)	−0.0012 (11)
C8	0.0893 (18)	0.0601 (14)	0.0639 (15)	−0.0234 (13)	−0.0149 (13)	−0.0012 (12)
C9	0.0757 (17)	0.0664 (16)	0.0665 (16)	−0.0149 (12)	−0.0150 (13)	−0.0047 (12)
C10	0.098 (2)	0.0719 (18)	0.082 (2)	−0.0179 (15)	−0.0083 (16)	−0.0175 (14)
C11	0.114 (2)	0.0604 (16)	0.098 (2)	−0.0283 (15)	−0.0061 (18)	−0.0100 (15)
C12	0.0861 (19)	0.0638 (16)	0.0819 (18)	−0.0268 (13)	−0.0108 (14)	0.0053 (13)
C13	0.109 (3)	0.089 (2)	0.068 (2)	−0.020 (2)	−0.008 (2)	−0.0094 (17)
O1	0.1232 (16)	0.0742 (12)	0.0787 (13)	−0.0397 (11)	−0.0029 (11)	0.0077 (9)
O2	0.1157 (16)	0.0851 (13)	0.0658 (12)	−0.0288 (11)	−0.0009 (10)	0.0022 (9)
N1	0.0818 (14)	0.0638 (12)	0.0560 (12)	−0.0253 (10)	−0.0094 (10)	0.0037 (9)
N2	0.0982 (16)	0.0621 (12)	0.0620 (13)	−0.0322 (11)	−0.0071 (11)	0.0015 (10)
S1	0.1117 (6)	0.0647 (4)	0.0625 (4)	−0.0339 (4)	−0.0004 (4)	−0.0005 (3)
F2	0.136 (8)	0.138 (5)	0.089 (5)	0.021 (5)	0.031 (4)	0.016 (4)
F1	0.163 (4)	0.182 (10)	0.086 (5)	−0.060 (4)	−0.054 (3)	0.026 (5)
F3	0.207 (8)	0.123 (7)	0.074 (3)	−0.091 (6)	0.020 (3)	−0.015 (3)
F11	0.41 (3)	0.196 (16)	0.067 (6)	−0.151 (18)	−0.075 (12)	0.003 (7)
F21	0.113 (8)	0.227 (14)	0.118 (12)	−0.063 (8)	0.011 (7)	0.006 (8)
F31	0.217 (12)	0.073 (7)	0.106 (8)	0.011 (6)	0.045 (6)	0.038 (5)
C1A	0.0672 (16)	0.0751 (16)	0.0594 (14)	−0.0291 (13)	−0.0031 (12)	0.0023 (12)
C2A	0.0668 (15)	0.0703 (15)	0.0507 (13)	−0.0261 (12)	−0.0040 (11)	−0.0008 (11)
C3A	0.0679 (16)	0.0687 (15)	0.0607 (15)	−0.0226 (12)	−0.0024 (12)	0.0025 (12)
C4A	0.0832 (19)	0.0805 (17)	0.0715 (17)	−0.0252 (14)	0.0075 (14)	0.0086 (14)
C5A	0.103 (2)	0.094 (2)	0.0589 (16)	−0.0181 (17)	0.0139 (15)	0.0060 (15)
C6A	0.110 (2)	0.091 (2)	0.0592 (17)	−0.0194 (17)	0.0034 (15)	−0.0131 (14)
C7A	0.0622 (14)	0.0672 (15)	0.0573 (14)	−0.0245 (11)	−0.0042 (11)	−0.0004 (11)
C8A	0.0800 (17)	0.0635 (15)	0.0594 (14)	−0.0247 (13)	−0.0023 (12)	−0.0035 (11)
C9A	0.0635 (15)	0.0742 (16)	0.0630 (15)	−0.0253 (12)	−0.0045 (12)	−0.0073 (12)
C10A	0.0750 (18)	0.0735 (17)	0.0778 (18)	−0.0154 (14)	−0.0004 (14)	−0.0146 (14)
C11A	0.0845 (19)	0.0595 (15)	0.101 (2)	−0.0181 (14)	−0.0119 (16)	−0.0042 (15)
C12A	0.0759 (17)	0.0647 (16)	0.0743 (17)	−0.0261 (13)	−0.0091 (13)	0.0072 (13)
C13A	0.091 (2)	0.095 (2)	0.0635 (19)	−0.031 (2)	0.0036 (17)	−0.0125 (17)
O1A	0.1020 (14)	0.0825 (12)	0.0745 (12)	−0.0487 (11)	0.0130 (10)	−0.0082 (9)
O2A	0.0917 (13)	0.0776 (11)	0.0596 (10)	−0.0294 (9)	0.0022 (9)	−0.0031 (8)
N1A	0.0781 (13)	0.0646 (12)	0.0553 (11)	−0.0304 (10)	0.0014 (10)	−0.0011 (9)
N2A	0.0778 (13)	0.0687 (13)	0.0573 (12)	−0.0334 (10)	0.0050 (10)	−0.0022 (10)
S1A	0.1139 (6)	0.0870 (5)	0.0643 (4)	−0.0586 (4)	0.0135 (4)	−0.0097 (3)
F2A	0.133 (4)	0.177 (9)	0.094 (4)	−0.046 (6)	−0.026 (4)	0.039 (5)
F3A	0.149 (5)	0.118 (4)	0.096 (6)	−0.033 (4)	0.059 (5)	−0.031 (4)
F1A	0.197 (9)	0.189 (8)	0.072 (2)	−0.150 (7)	−0.003 (5)	−0.005 (4)
F2B	0.178 (14)	0.104 (6)	0.094 (7)	0.020 (7)	0.056 (7)	0.040 (5)
F1B	0.106 (6)	0.248 (17)	0.164 (11)	−0.091 (8)	−0.016 (5)	0.084 (11)
F3B	0.35 (2)	0.20 (2)	0.059 (5)	−0.14 (2)	−0.011 (11)	−0.030 (7)

Geometric parameters (Å, º) top

C1—O1	1.224 (3)	C1A—O1A	1.223 (3)
C1—N1	1.376 (3)	C1A—N1A	1.376 (3)
C1—C3	1.448 (3)	C1A—C3A	1.449 (3)
C2—N2	1.334 (3)	C2A—N2A	1.336 (3)
C2—N1	1.391 (3)	C2A—N1A	1.390 (3)
C2—S1	1.649 (2)	C2A—S1A	1.648 (2)
C3—C4	1.333 (3)	C3A—C4A	1.344 (3)
C3—O2	1.355 (3)	C3A—O2A	1.365 (3)
C4—C5	1.412 (4)	C4A—C5A	1.401 (4)
C4—H4	0.93	C4A—H4A	0.93
C5—C6	1.312 (4)	C5A—C6A	1.328 (4)
C5—H5	0.93	C5A—H5A	0.93
C6—O2	1.354 (3)	C6A—O2A	1.357 (3)
C6—H6	0.93	C6A—H6A	0.93
C7—C12	1.379 (3)	C7A—C12A	1.378 (3)
C7—C8	1.388 (3)	C7A—C8A	1.387 (3)
C7—N2	1.408 (3)	C7A—N2A	1.409 (3)
C8—C9	1.372 (3)	C8A—C9A	1.377 (3)
C8—H8	0.93	C8A—H8A	0.93
C9—C10	1.380 (4)	C9A—C10A	1.379 (3)
C9—C13	1.490 (4)	C9A—C13A	1.487 (4)
C10—C11	1.357 (4)	C10A—C11A	1.374 (4)
C10—H10	0.93	C10A—H10A	0.93
C11—C12	1.371 (4)	C11A—C12A	1.368 (4)
C11—H11	0.93	C11A—H11A	0.93
C12—H12	0.93	C12A—H12A	0.93
C13—F2	1.299 (12)	C13A—F1A	1.281 (7)
C13—F1	1.303 (11)	C13A—F3A	1.296 (9)
C13—F3	1.322 (8)	C13A—F2A	1.335 (8)
N1—H1	0.86	N1A—H1A	0.86
N2—H2	0.86	N2A—H2A	0.86

O1—C1—N1	123.1 (2)	O1A—C1A—N1A	122.9 (2)
O1—C1—C3	121.0 (2)	O1A—C1A—C3A	120.9 (2)
N1—C1—C3	116.0 (2)	N1A—C1A—C3A	116.2 (2)
N2—C2—N1	114.0 (2)	N2A—C2A—N1A	114.75 (19)
N2—C2—S1	127.68 (18)	N2A—C2A—S1A	127.02 (17)
N1—C2—S1	118.35 (17)	N1A—C2A—S1A	118.22 (18)
C4—C3—O2	109.7 (2)	C4A—C3A—O2A	109.9 (2)
C4—C3—C1	132.1 (3)	C4A—C3A—C1A	132.0 (2)
O2—C3—C1	118.2 (2)	O2A—C3A—C1A	118.1 (2)
C3—C4—C5	106.4 (3)	C3A—C4A—C5A	106.5 (2)
C3—C4—H4	126.8	C3A—C4A—H4A	126.8
C5—C4—H4	126.8	C5A—C4A—H4A	126.8
C6—C5—C4	107.0 (3)	C6A—C5A—C4A	107.2 (2)
C6—C5—H5	126.5	C6A—C5A—H5A	126.4
C4—C5—H5	126.5	C4A—C5A—H5A	126.4
C5—C6—O2	110.4 (3)	C5A—C6A—O2A	110.5 (3)
C5—C6—H6	124.8	C5A—C6A—H6A	124.8
O2—C6—H6	124.8	O2A—C6A—H6A	124.8
C12—C7—C8	119.0 (2)	C12A—C7A—C8A	119.2 (2)
C12—C7—N2	115.4 (2)	C12A—C7A—N2A	116.9 (2)
C8—C7—N2	125.5 (2)	C8A—C7A—N2A	123.9 (2)
C9—C8—C7	119.6 (2)	C9A—C8A—C7A	119.7 (2)
C9—C8—H8	120.2	C9A—C8A—H8A	120.2
C7—C8—H8	120.2	C7A—C8A—H8A	120.2
C8—C9—C10	120.8 (2)	C8A—C9A—C10A	120.8 (2)
C8—C9—C13	119.8 (2)	C8A—C9A—C13A	118.5 (2)
C10—C9—C13	119.4 (3)	C10A—C9A—C13A	120.7 (2)
C11—C10—C9	119.2 (3)	C11A—C10A—C9A	119.2 (2)
C11—C10—H10	120.4	C11A—C10A—H10A	120.4
C9—C10—H10	120.4	C9A—C10A—H10A	120.4
C10—C11—C12	120.9 (3)	C12A—C11A—C10A	120.5 (2)
C10—C11—H11	119.6	C12A—C11A—H11A	119.7
C12—C11—H11	119.6	C10A—C11A—H11A	119.7
C11—C12—C7	120.4 (3)	C11A—C12A—C7A	120.7 (2)
C11—C12—H12	119.8	C11A—C12A—H12A	119.6
C7—C12—H12	119.8	C7A—C12A—H12A	119.6
F2—C13—F1	103.4 (9)	F1A—C13A—F3A	107.4 (7)
F2—C13—F3	103.2 (9)	F1A—C13A—F2A	104.8 (6)
F1—C13—F3	104.9 (8)	F3A—C13A—F2A	102.3 (6)
F2—C13—C9	115.6 (5)	F1A—C13A—C9A	114.6 (4)
F1—C13—C9	114.0 (6)	F3A—C13A—C9A	114.2 (6)
F3—C13—C9	114.4 (5)	F2A—C13A—C9A	112.4 (4)
C6—O2—C3	106.6 (2)	C6A—O2A—C3A	106.0 (2)
C1—N1—C2	128.9 (2)	C1A—N1A—C2A	128.6 (2)
C1—N1—H1	115.6	C1A—N1A—H1A	115.7
C2—N1—H1	115.6	C2A—N1A—H1A	115.7
C2—N2—C7	132.2 (2)	C2A—N2A—C7A	130.37 (19)
C2—N2—H2	113.9	C2A—N2A—H2A	114.8
C7—N2—H2	113.9	C7A—N2A—H2A	114.8

O1—C1—C3—C4	0.4 (5)	O1A—C1A—C3A—C4A	0.3 (5)
N1—C1—C3—C4	−179.9 (3)	N1A—C1A—C3A—C4A	−178.7 (3)
O1—C1—C3—O2	180.0 (2)	O1A—C1A—C3A—O2A	178.2 (2)
N1—C1—C3—O2	−0.3 (3)	N1A—C1A—C3A—O2A	−0.8 (3)
O2—C3—C4—C5	0.9 (3)	O2A—C3A—C4A—C5A	−0.4 (3)
C1—C3—C4—C5	−179.4 (3)	C1A—C3A—C4A—C5A	177.6 (3)
C3—C4—C5—C6	−0.7 (4)	C3A—C4A—C5A—C6A	0.1 (4)
C4—C5—C6—O2	0.2 (4)	C4A—C5A—C6A—O2A	0.2 (4)
C12—C7—C8—C9	−0.8 (4)	C12A—C7A—C8A—C9A	−1.9 (4)
N2—C7—C8—C9	177.7 (2)	N2A—C7A—C8A—C9A	−179.7 (2)
C7—C8—C9—C10	0.7 (4)	C7A—C8A—C9A—C10A	1.6 (4)
C7—C8—C9—C13	−177.2 (3)	C7A—C8A—C9A—C13A	−178.1 (3)
C8—C9—C10—C11	0.1 (4)	C8A—C9A—C10A—C11A	−0.6 (4)
C13—C9—C10—C11	178.0 (3)	C13A—C9A—C10A—C11A	179.1 (3)
C9—C10—C11—C12	−0.8 (5)	C9A—C10A—C11A—C12A	0.1 (4)
C10—C11—C12—C7	0.7 (5)	C10A—C11A—C12A—C7A	−0.5 (4)
C8—C7—C12—C11	0.1 (4)	C8A—C7A—C12A—C11A	1.4 (4)
N2—C7—C12—C11	−178.5 (3)	N2A—C7A—C12A—C11A	179.3 (2)
C8—C9—C13—F2	−126.8 (9)	C8A—C9A—C13A—F1A	51.0 (9)
C10—C9—C13—F2	55.2 (10)	C10A—C9A—C13A—F1A	−128.7 (9)
C8—C9—C13—F1	113.5 (7)	C8A—C9A—C13A—F3A	175.5 (6)
C10—C9—C13—F1	−64.4 (8)	C10A—C9A—C13A—F3A	−4.2 (7)
C8—C9—C13—F3	−7.2 (7)	C8A—C9A—C13A—F2A	−68.5 (7)
C10—C9—C13—F3	174.9 (6)	C10A—C9A—C13A—F2A	111.8 (7)
C5—C6—O2—C3	0.4 (4)	C5A—C6A—O2A—C3A	−0.4 (3)
C4—C3—O2—C6	−0.8 (3)	C4A—C3A—O2A—C6A	0.5 (3)
C1—C3—O2—C6	179.4 (2)	C1A—C3A—O2A—C6A	−177.8 (2)
O1—C1—N1—C2	2.3 (4)	O1A—C1A—N1A—C2A	−11.4 (4)
C3—C1—N1—C2	−177.4 (2)	C3A—C1A—N1A—C2A	167.5 (2)
N2—C2—N1—C1	−5.4 (4)	N2A—C2A—N1A—C1A	7.6 (4)
S1—C2—N1—C1	174.32 (19)	S1A—C2A—N1A—C1A	−171.20 (19)
N1—C2—N2—C7	−177.3 (2)	N1A—C2A—N2A—C7A	−175.4 (2)
S1—C2—N2—C7	3.0 (4)	S1A—C2A—N2A—C7A	3.3 (4)
C12—C7—N2—C2	176.1 (3)	C12A—C7A—N2A—C2A	153.4 (2)
C8—C7—N2—C2	−2.4 (4)	C8A—C7A—N2A—C2A	−28.8 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···S1Aⁱ	0.86	2.78	3.643 (2)	176
N1—H1···O2	0.86	2.27	2.692 (3)	110
N1A—H1A···S1ⁱⁱ	0.86	2.74	3.592 (2)	173
N1A—H1A···O2A	0.86	2.30	2.700 (3)	108
N2—H2···O1	0.86	1.88	2.625 (3)	144
N2A—H2A···O1A	0.86	1.92	2.640 (3)	140

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

Experimental details

Crystal data
Chemical formula	C₁₃H₉F₃N₂O₂S
M_r	314.29
Crystal system, space group	Triclinic, P1
Temperature (K)	294
a, b, c (Å)	7.5540 (14), 13.684 (5), 14.210 (3)
α, β, γ (°)	86.124 (13), 74.779 (7), 74.065 (8)
V (Å³)	1362.9 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.28
Crystal size (mm)	0.09 × 0.07 × 0.03

Data collection
Diffractometer	Enraf–Nonius KappaCCD diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	9271, 4953, 2925
R_int	0.035
(sin θ/λ)_max (Å⁻¹)	0.602

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.044, 0.123, 1.01
No. of reflections	4953
No. of parameters	433
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.14, −0.24

Computer programs: COLLECT (Nonius, 2000), DENZO and SCALEPACK (Otwinowski & Minor, 1997), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997) and Mercury (Macrae et al., 2006), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···S1Aⁱ	0.86	2.78	3.643 (2)	176
N1—H1···O2	0.86	2.27	2.692 (3)	110
N1A—H1A···S1ⁱⁱ	0.86	2.74	3.592 (2)	173
N1A—H1A···O2A	0.86	2.30	2.700 (3)	108
N2—H2···O1	0.86	1.88	2.625 (3)	144
N2A—H2A···O1A	0.86	1.92	2.640 (3)	140

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

Acknowledgements

The authors acknowledge financial support from the Brazilian agency CNPq. OEH thanks CONACyT of Mexico for research grant No. 61541.

References

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