1-Furoyl-3-[3-(trifluoro-meth-yl)phen-yl]thio-urea.

The title compound, C(13)H(9)F(3)N(2)O(2)S, crystallizes with two independent mol-ecules in the asymmetric unit. The central thio-urea 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 mol-ecules. The trans-cis geometry of the thio-urea fragment is stabilized by an intra-molecular N-H⋯O hydrogen bond between the H atom of the cis thio-amide and the carbonyl O atom. In the crystal structure, inter-molecular 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 = 314.29

Triclinic,

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[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.123

S = 1.01

4953 reflections

433 parameters

H-atom parameters constrained

Δρmax = 0.14 e Å−3

Δρmin = −0.24 e Å−3

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 ▶).

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

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

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C13H9F3N2O2S	Z = 4
Mr = 314.29	F(000) = 640
Triclinic, P1	Dx = 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

Enraf–Nonius KappaCCD diffractometer	2925 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube Enraf Nonius FR590	Rint = 0.035
horizontally mounted graphite crystal	θmax = 25.4°, θmin = 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 on F2	0 restraints
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.044	w = 1/[σ2(Fo2) + (0.058P)2 + 0.0881P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.123	(Δ/σ)max < 0.001
S = 1.01	Δρmax = 0.14 e Å−3
4953 reflections	Δρmin = −0.24 e Å−3
433 parameters

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.

	x	y	z	Uiso*/Ueq	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

	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)

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)

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

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) ; (ii) .