N-(5-Nitro-1,3-thia­zol-2-yl)-4-(tri­fluoro­meth­yl)benzamide

Liu, X.-W.; Zhang, H.; Yang, Y.-J.; Li, J.-Y.; Zhang, J.-Y.

doi:10.1107/S1600536813011264

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 69| Part 6| June 2013| Page o943

doi:10.1107/S1600536813011264

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N-(5-Nitro-1,3-thiazol-2-yl)-4-(trifluoromethyl)benzamide

Xi-Wang Liu,^a Han Zhang,^a Ya-Jun Yang,^a Jian-Yong Li ^a ^* and Ji-Yu Zhang ^a

^aKey Laboratory of New Animal Drug Project, Gansu Province, Key Laboratory of Veterinary Pharmaceutical Development, Ministry of Agriculture, Lanzhou Institute of Animal Science and Veterinary Pharmaceutics of CAAS, Lanzhou 730050, People's Republic of China
^*Correspondence e-mail: lijy1971@163.com

(Received 16 April 2013; accepted 25 April 2013; online 22 May 2013)

There are two independent and conformationally dissimilar molecules (A and B) in the asymmetric unit of the title compound, C₁₁H₆F₃N₃O₃S; the dihedral angles between the benzene and thiazole rings are 33.8 (2)° in A and 59.7 (2)° in B. The similarity of the C—N bond lengths in the amide group [1.379 (5) and 1.358 (5) Å for A, and 1.365 (5) and 1.363 (5) Å for B] indicates the presence of conjugation between the two rings. In the crystal, molecules are linked by N—H⋯N hydrogen bonds, forming chains extending along [010]; weak N—H⋯O_amide interactions are also present in the structure.

Related literature

For the antiparasitic activity of nitazoxanide, see: Fox & Saravolatz (2005 ) and for the antibacterial activity of thiazolides, see: Gargala et al. (2010 ); Stachulski et al. (2011 ). For the synthesis and antibacterial activity of the title compound, see: Ballard et al. (2011 ).

Experimental

Crystal data

C₁₁H₆F₃N₃O₃S
M_r = 317.26
Monoclinic, P 2₁ /c
a = 12.362 (4) Å
b = 8.946 (3) Å
c = 23.261 (8) Å
β = 100.762 (4)°
V = 2527.2 (15) Å³
Z = 8
Mo Kα radiation
μ = 0.31 mm⁻¹
T = 296 K
0.34 × 0.32 × 0.25 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.903, T_max = 0.927
11671 measured reflections
4588 independent reflections
3183 reflections with I > 2σ(I)
R_int = 0.039

Refinement

R[F² > 2σ(F²)] = 0.069
wR(F²) = 0.175
S = 1.06
4588 reflections
379 parameters
H-atom parameters constrained
Δρ_max = 0.50 e Å⁻³
Δρ_min = −0.48 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯N5ⁱ	0.86	2.32	3.044 (5)	142
N1—H1⋯O3ⁱ	0.86	2.57	3.023 (5)	115
N4—H4⋯N2ⁱⁱ	0.86	2.18	2.939 (5)	147
N4—H4⋯O2	0.86	2.62	3.146 (5)	121
Symmetry codes: (i) $[-x, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) $[-x, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2008 ); cell refinement: SAINT (Bruker, 2008); 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.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536813011264/zs2257sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813011264/zs2257Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536813011264/zs2257Isup3.cml

checkCIF report

Comment top

Parasitic and bacterial infections represnt a significant cause of morbidity and mortality worldwide (Fox & Saravolatz, 2005). Nitazoxanide is a novel antiparasitic compound developed for both human and animal use and is the parent compound of a class of drugs named thiazolides. Recently, a number of thiazolides were synthesized and their biological activities were also evaluated (Gargala et al., 2010); Stachulski et al., 2011). The title compound C₁₁H₆F₃N₃O₃S is a new thiazolide which displays higher antibacterial activity than nitazoxanide (Ballard et al., 2011) and the crystal structure is reported herein.

In this structure, there are two independent and conformationally dissimilar molecules in the asymmetric unit (Fig. 1) [dihedral angles between the benzene and thiazole rings: 33.8 (2) and 59.7 (2)°]. In the crystal, the molecules are linked by intermolecular N—H···N hydrogen bonds (Table 2), giving one-dimensional chains extending along [010]. Also present in the structure are intra- and intermolecular N—H···O_amide interactions within the chains.

The similarity of the C—N bond lengths [N1—C8, 1.379 (5) Å and N1—C9, 1.358 (5) Å] in the amide group indicates the presence of conjugation between the two rings, which confirms the hypothetical mechanism with thiazolides that the amin anion may interact with the target PFOR enzyme.

Related literature top

For the antiparasitic activity of nitazoxanide, see: Fox & Saravolatz (2005) and for the antibacterial activity of thiazolides, see: Gargala et al. (2010); Stachulski et al. (2011). For the synthesis and antibacterial activity of the title compound, see: Ballard et al. (2011).

Experimental top

To a solution of 5-nitrothiazol-2-amine (1 mmol) in distilled pyridine was added a equimolar amount of 4-trifluorobenzoyl chloride with stirring. After the addition was complete, the reaction mixture was allowed to stand overnight. The reaction was judged complete by TLC analysis. The crude product that separated on dilution was filtered, washed with 10% sodium bicarbonate solution, then several times with water. The dry solid was purified by chromatography to give the pure title compound and crystals suitable for single crystal X-ray analysis were obtained by recrystallization from methanol.

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); 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).

Figures top

Fig. 1. The molecular conformation and atom numbering scheme for the two independent molecules in the asymmetric unit of title compound, with displacement ellipsoids drawn at the 30% probability level.

N-(5-Nitro-1,3-thiazol-2-yl)-4-(trifluoromethyl)benzamide top

Crystal data top

C₁₁H₆F₃N₃O₃S	F(000) = 1280
M_r = 317.26	D_x = 1.668 Mg m⁻³
Monoclinic, P2₁/c	Melting point = 487–489 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 12.362 (4) Å	Cell parameters from 2723 reflections
b = 8.946 (3) Å	θ = 2.4–24.6°
c = 23.261 (8) Å	µ = 0.31 mm⁻¹
β = 100.762 (4)°	T = 296 K
V = 2527.2 (15) Å³	Block, colourless
Z = 8	0.34 × 0.32 × 0.25 mm

Data collection top

Bruker APEXII CCD diffractometer	4588 independent reflections
Radiation source: fine-focus sealed tube	3183 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.039
ϕ and ω scans	θ_max = 25.5°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −14→14
T_min = 0.903, T_max = 0.927	k = −9→10
11671 measured reflections	l = −28→26

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.069	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.175	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.0692P)² + 3.2322P] where P = (F_o² + 2F_c²)/3
4588 reflections	(Δ/σ)_max = 0.001
379 parameters	Δρ_max = 0.50 e Å⁻³
0 restraints	Δρ_min = −0.48 e Å⁻³

Crystal data top

C₁₁H₆F₃N₃O₃S	V = 2527.2 (15) Å³
M_r = 317.26	Z = 8
Monoclinic, P2₁/c	Mo Kα radiation
a = 12.362 (4) Å	µ = 0.31 mm⁻¹
b = 8.946 (3) Å	T = 296 K
c = 23.261 (8) Å	0.34 × 0.32 × 0.25 mm
β = 100.762 (4)°

Data collection top

Bruker APEXII CCD diffractometer	4588 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3183 reflections with I > 2σ(I)
T_min = 0.903, T_max = 0.927	R_int = 0.039
11671 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.069	0 restraints
wR(F²) = 0.175	H-atom parameters constrained
S = 1.06	Δρ_max = 0.50 e Å⁻³
4588 reflections	Δρ_min = −0.48 e Å⁻³
379 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.

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 > σ(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	0.2871 (3)	0.2306 (5)	0.10652 (16)	0.0387 (10)
C2	0.2390 (3)	0.1247 (5)	0.06679 (17)	0.0448 (11)
H2	0.1799	0.0687	0.0743	0.054*
C3	0.2787 (4)	0.1018 (5)	0.01590 (18)	0.0483 (11)
H3	0.2467	0.0296	−0.0107	0.058*
C4	0.3654 (3)	0.1855 (5)	0.00447 (18)	0.0471 (11)
C5	0.4138 (4)	0.2911 (6)	0.0439 (2)	0.0549 (13)
H5	0.4721	0.3481	0.0360	0.066*
C6	0.3758 (3)	0.3125 (5)	0.09514 (19)	0.0498 (12)
H6	0.4098	0.3821	0.1223	0.060*
C7	0.4053 (5)	0.1639 (8)	−0.0515 (2)	0.0687 (16)
C8	0.2493 (3)	0.2599 (5)	0.16232 (17)	0.0391 (10)
C9	0.0895 (3)	0.2764 (5)	0.20673 (16)	0.0357 (9)
C10	−0.0463 (4)	0.3137 (5)	0.25281 (17)	0.0459 (11)
H10	−0.1190	0.3152	0.2583	0.055*
C11	0.0372 (3)	0.3595 (5)	0.29379 (16)	0.0388 (10)
C12	0.3086 (3)	0.8380 (5)	0.34839 (17)	0.0401 (10)
C13	0.3064 (4)	0.7008 (5)	0.32116 (18)	0.0461 (11)
H13	0.2820	0.6166	0.3384	0.055*
C14	0.3405 (4)	0.6892 (5)	0.26822 (19)	0.0490 (11)
H14	0.3404	0.5965	0.2502	0.059*
C15	0.3746 (3)	0.8129 (5)	0.24206 (18)	0.0436 (10)
C16	0.3762 (4)	0.9502 (6)	0.2691 (2)	0.0554 (12)
H16	0.3984	1.0348	0.2512	0.066*
C17	0.3448 (4)	0.9620 (6)	0.32261 (19)	0.0545 (12)
H17	0.3481	1.0541	0.3414	0.065*
C18	0.4075 (4)	0.8034 (7)	0.1841 (2)	0.0587 (13)
C19	0.2738 (3)	0.8557 (5)	0.40602 (17)	0.0426 (10)
C20	0.1252 (3)	0.8112 (5)	0.45709 (16)	0.0377 (9)
C21	0.0747 (4)	0.8551 (5)	0.54822 (17)	0.0417 (10)
C22	−0.0063 (4)	0.7988 (5)	0.50768 (17)	0.0454 (11)
H22	−0.0763	0.7793	0.5151	0.054*
F1	0.4126 (4)	0.0182 (5)	−0.06394 (15)	0.1155 (15)
F2	0.3376 (3)	0.2148 (5)	−0.09695 (13)	0.0960 (12)
F3	0.5002 (3)	0.2196 (7)	−0.05158 (16)	0.158 (2)
F4	0.4257 (4)	0.6685 (5)	0.16786 (16)	0.1311 (18)
F5	0.3324 (4)	0.8501 (5)	0.14227 (14)	0.1252 (17)
F6	0.4934 (4)	0.8772 (8)	0.18052 (17)	0.184 (3)
N1	0.1382 (3)	0.2403 (4)	0.16086 (13)	0.0382 (8)
H1	0.0982	0.2039	0.1298	0.046*
N2	−0.0176 (3)	0.2646 (4)	0.20246 (14)	0.0445 (9)
N3	0.0305 (3)	0.4175 (4)	0.34971 (15)	0.0446 (9)
N4	0.1728 (3)	0.7979 (4)	0.40900 (13)	0.0416 (9)
H4	0.1375	0.7507	0.3791	0.050*
N5	0.0219 (3)	0.7725 (4)	0.45493 (14)	0.0437 (9)
N6	0.0665 (4)	0.8983 (4)	0.60621 (15)	0.0503 (10)
O1	0.3090 (2)	0.3016 (4)	0.20642 (12)	0.0560 (9)
O2	0.1160 (3)	0.4596 (4)	0.38111 (13)	0.0638 (9)
O3	−0.0597 (3)	0.4226 (4)	0.36369 (13)	0.0587 (9)
O4	0.3288 (2)	0.9184 (4)	0.44772 (13)	0.0632 (10)
O5	0.1513 (3)	0.9334 (4)	0.63961 (14)	0.0713 (11)
O6	−0.0250 (3)	0.8991 (4)	0.61955 (13)	0.0647 (10)
S1	0.16224 (9)	0.34362 (13)	0.27209 (4)	0.0429 (3)
S2	0.19504 (9)	0.88052 (14)	0.52279 (4)	0.0469 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.037 (2)	0.045 (3)	0.035 (2)	0.0080 (19)	0.0076 (17)	0.0032 (19)
C2	0.046 (3)	0.046 (3)	0.045 (2)	−0.001 (2)	0.014 (2)	−0.002 (2)
C3	0.051 (3)	0.051 (3)	0.044 (2)	0.002 (2)	0.012 (2)	−0.006 (2)
C4	0.041 (2)	0.062 (3)	0.039 (2)	0.012 (2)	0.0087 (19)	0.004 (2)
C5	0.041 (3)	0.072 (4)	0.056 (3)	−0.003 (2)	0.020 (2)	0.000 (3)
C6	0.041 (2)	0.061 (3)	0.048 (3)	−0.008 (2)	0.010 (2)	−0.011 (2)
C7	0.063 (3)	0.103 (5)	0.046 (3)	0.000 (3)	0.024 (3)	−0.009 (3)
C8	0.041 (2)	0.041 (3)	0.036 (2)	0.0028 (19)	0.0087 (18)	0.0055 (19)
C9	0.043 (2)	0.034 (2)	0.0299 (19)	−0.0021 (18)	0.0073 (17)	0.0037 (17)
C10	0.044 (2)	0.058 (3)	0.037 (2)	0.001 (2)	0.0133 (19)	0.001 (2)
C11	0.048 (2)	0.040 (3)	0.030 (2)	0.0028 (19)	0.0099 (18)	0.0008 (17)
C12	0.030 (2)	0.049 (3)	0.041 (2)	−0.0009 (19)	0.0060 (17)	−0.004 (2)
C13	0.051 (3)	0.044 (3)	0.045 (2)	0.000 (2)	0.016 (2)	0.002 (2)
C14	0.051 (3)	0.048 (3)	0.050 (3)	0.004 (2)	0.016 (2)	−0.006 (2)
C15	0.038 (2)	0.053 (3)	0.040 (2)	0.004 (2)	0.0078 (18)	0.003 (2)
C16	0.064 (3)	0.049 (3)	0.056 (3)	−0.007 (2)	0.018 (2)	0.005 (2)
C17	0.068 (3)	0.047 (3)	0.053 (3)	−0.005 (2)	0.023 (2)	−0.008 (2)
C18	0.059 (3)	0.074 (4)	0.045 (3)	0.003 (3)	0.016 (2)	0.005 (3)
C19	0.039 (2)	0.050 (3)	0.037 (2)	0.002 (2)	0.0039 (18)	−0.003 (2)
C20	0.039 (2)	0.042 (3)	0.031 (2)	0.0013 (19)	0.0056 (17)	−0.0026 (18)
C21	0.056 (3)	0.037 (3)	0.033 (2)	0.001 (2)	0.0115 (19)	0.0004 (18)
C22	0.050 (3)	0.051 (3)	0.039 (2)	0.000 (2)	0.0152 (19)	0.003 (2)
F1	0.169 (4)	0.117 (3)	0.075 (2)	0.048 (3)	0.059 (2)	−0.008 (2)
F2	0.112 (3)	0.133 (3)	0.0448 (17)	0.011 (2)	0.0194 (17)	0.0211 (19)
F3	0.090 (3)	0.313 (7)	0.089 (3)	−0.080 (4)	0.064 (2)	−0.076 (3)
F4	0.226 (5)	0.101 (3)	0.092 (3)	0.061 (3)	0.098 (3)	0.013 (2)
F5	0.147 (4)	0.181 (4)	0.0498 (19)	0.073 (3)	0.024 (2)	0.027 (2)
F6	0.158 (4)	0.329 (8)	0.090 (3)	−0.157 (5)	0.085 (3)	−0.081 (4)
N1	0.0384 (19)	0.046 (2)	0.0310 (17)	−0.0039 (16)	0.0083 (14)	−0.0060 (15)
N2	0.038 (2)	0.062 (3)	0.0349 (18)	−0.0076 (18)	0.0106 (15)	−0.0049 (17)
N3	0.065 (3)	0.036 (2)	0.0355 (19)	0.0040 (18)	0.0157 (19)	0.0006 (16)
N4	0.0377 (19)	0.055 (2)	0.0325 (17)	−0.0058 (16)	0.0077 (14)	−0.0091 (16)
N5	0.044 (2)	0.053 (2)	0.0353 (18)	−0.0043 (18)	0.0119 (15)	−0.0030 (16)
N6	0.081 (3)	0.034 (2)	0.037 (2)	0.002 (2)	0.014 (2)	−0.0004 (17)
O1	0.0428 (17)	0.088 (3)	0.0343 (16)	0.0002 (17)	0.0013 (13)	−0.0087 (16)
O2	0.078 (2)	0.073 (3)	0.0379 (17)	−0.006 (2)	0.0045 (17)	−0.0150 (17)
O3	0.073 (2)	0.056 (2)	0.0556 (19)	0.0123 (17)	0.0336 (17)	−0.0024 (16)
O4	0.0457 (18)	0.097 (3)	0.0468 (18)	−0.0171 (18)	0.0080 (15)	−0.0243 (18)
O5	0.101 (3)	0.070 (3)	0.0410 (18)	−0.009 (2)	0.0067 (19)	−0.0184 (17)
O6	0.092 (3)	0.058 (2)	0.054 (2)	0.0106 (19)	0.0380 (19)	0.0038 (16)
S1	0.0430 (6)	0.0545 (8)	0.0309 (5)	−0.0044 (5)	0.0063 (4)	−0.0053 (5)
S2	0.0490 (7)	0.0570 (8)	0.0335 (5)	−0.0026 (6)	0.0046 (5)	−0.0070 (5)

Geometric parameters (Å, º) top

C1—C2	1.379 (6)	C13—C14	1.378 (6)
C1—C6	1.385 (6)	C13—H13	0.9300
C1—C8	1.483 (5)	C14—C15	1.367 (6)
C2—C3	1.378 (6)	C14—H14	0.9300
C2—H2	0.9300	C15—C16	1.379 (6)
C3—C4	1.374 (6)	C15—C18	1.482 (6)
C3—H3	0.9300	C16—C17	1.374 (6)
C4—C5	1.375 (6)	C16—H16	0.9300
C4—C7	1.488 (6)	C17—H17	0.9300
C5—C6	1.372 (6)	C18—F6	1.266 (6)
C5—H5	0.9300	C18—F5	1.283 (6)
C6—H6	0.9300	C18—F4	1.297 (6)
C7—F3	1.275 (6)	C19—O4	1.213 (5)
C7—F2	1.303 (6)	C19—N4	1.365 (5)
C7—F1	1.342 (7)	C20—N5	1.314 (5)
C8—O1	1.205 (5)	C20—N4	1.363 (5)
C8—N1	1.379 (5)	C20—S2	1.724 (4)
C9—N2	1.314 (5)	C21—C22	1.339 (6)
C9—N1	1.358 (5)	C21—N6	1.425 (5)
C9—S1	1.723 (4)	C21—S2	1.716 (4)
C10—C11	1.333 (6)	C22—N5	1.358 (5)
C10—N2	1.359 (5)	C22—H22	0.9300
C10—H10	0.9300	N1—H1	0.8600
C11—N3	1.417 (5)	N3—O3	1.220 (4)
C11—S1	1.719 (4)	N3—O2	1.227 (5)
C12—C17	1.375 (6)	N4—H4	0.8600
C12—C13	1.379 (6)	N6—O5	1.224 (5)
C12—C19	1.491 (5)	N6—O6	1.227 (5)

C2—C1—C6	119.5 (4)	C13—C14—H14	119.7
C2—C1—C8	122.8 (4)	C14—C15—C16	119.8 (4)
C6—C1—C8	117.7 (4)	C14—C15—C18	121.3 (4)
C3—C2—C1	120.0 (4)	C16—C15—C18	118.9 (4)
C3—C2—H2	120.0	C17—C16—C15	120.0 (4)
C1—C2—H2	120.0	C17—C16—H16	120.0
C2—C3—C4	120.1 (4)	C15—C16—H16	120.0
C2—C3—H3	120.0	C16—C17—C12	120.2 (4)
C4—C3—H3	120.0	C16—C17—H17	119.9
C5—C4—C3	120.2 (4)	C12—C17—H17	119.9
C5—C4—C7	120.0 (4)	F6—C18—F5	106.1 (5)
C3—C4—C7	119.8 (4)	F6—C18—F4	105.9 (5)
C6—C5—C4	119.9 (4)	F5—C18—F4	102.8 (5)
C6—C5—H5	120.0	F6—C18—C15	114.0 (4)
C4—C5—H5	120.0	F5—C18—C15	112.9 (4)
C5—C6—C1	120.2 (4)	F4—C18—C15	114.2 (4)
C5—C6—H6	119.9	O4—C19—N4	121.1 (4)
C1—C6—H6	119.9	O4—C19—C12	123.8 (4)
F3—C7—F2	108.3 (5)	N4—C19—C12	115.2 (3)
F3—C7—F1	106.3 (5)	N5—C20—N4	120.7 (3)
F2—C7—F1	102.9 (5)	N5—C20—S2	116.8 (3)
F3—C7—C4	114.0 (5)	N4—C20—S2	122.5 (3)
F2—C7—C4	113.4 (4)	C22—C21—N6	126.4 (4)
F1—C7—C4	111.2 (5)	C22—C21—S2	112.9 (3)
O1—C8—N1	120.6 (4)	N6—C21—S2	120.6 (3)
O1—C8—C1	123.9 (4)	C21—C22—N5	114.7 (4)
N1—C8—C1	115.6 (3)	C21—C22—H22	122.7
N2—C9—N1	120.6 (3)	N5—C22—H22	122.7
N2—C9—S1	116.6 (3)	C9—N1—C8	122.4 (3)
N1—C9—S1	122.8 (3)	C9—N1—H1	118.8
C11—C10—N2	115.0 (4)	C8—N1—H1	118.8
C11—C10—H10	122.5	C9—N2—C10	109.3 (3)
N2—C10—H10	122.5	O3—N3—O2	124.0 (4)
C10—C11—N3	126.8 (4)	O3—N3—C11	118.1 (4)
C10—C11—S1	112.6 (3)	O2—N3—C11	117.9 (4)
N3—C11—S1	120.6 (3)	C19—N4—C20	123.2 (3)
C17—C12—C13	119.9 (4)	C19—N4—H4	118.4
C17—C12—C19	118.6 (4)	C20—N4—H4	118.4
C13—C12—C19	121.6 (4)	C20—N5—C22	109.4 (3)
C14—C13—C12	119.6 (4)	O5—N6—O6	124.0 (4)
C14—C13—H13	120.2	O5—N6—C21	117.8 (4)
C12—C13—H13	120.2	O6—N6—C21	118.2 (4)
C15—C14—C13	120.6 (4)	C11—S1—C9	86.47 (19)
C15—C14—H14	119.7	C21—S2—C20	86.26 (19)

C6—C1—C2—C3	−0.6 (6)	C16—C15—C18—F4	166.3 (5)
C8—C1—C2—C3	−179.4 (4)	C17—C12—C19—O4	−50.0 (6)
C1—C2—C3—C4	−0.6 (7)	C13—C12—C19—O4	129.2 (5)
C2—C3—C4—C5	0.7 (7)	C17—C12—C19—N4	129.0 (4)
C2—C3—C4—C7	−177.9 (4)	C13—C12—C19—N4	−51.8 (6)
C3—C4—C5—C6	0.4 (7)	N6—C21—C22—N5	177.4 (4)
C7—C4—C5—C6	179.1 (5)	S2—C21—C22—N5	0.2 (5)
C4—C5—C6—C1	−1.7 (7)	N2—C9—N1—C8	175.9 (4)
C2—C1—C6—C5	1.8 (7)	S1—C9—N1—C8	−2.5 (6)
C8—C1—C6—C5	−179.4 (4)	O1—C8—N1—C9	4.8 (6)
C5—C4—C7—F3	17.1 (8)	C1—C8—N1—C9	−173.6 (4)
C3—C4—C7—F3	−164.2 (5)	N1—C9—N2—C10	−177.1 (4)
C5—C4—C7—F2	−107.4 (6)	S1—C9—N2—C10	1.3 (5)
C3—C4—C7—F2	71.3 (7)	C11—C10—N2—C9	−0.6 (6)
C5—C4—C7—F1	137.3 (5)	C10—C11—N3—O3	2.6 (7)
C3—C4—C7—F1	−44.1 (7)	S1—C11—N3—O3	−178.0 (3)
C2—C1—C8—O1	149.3 (4)	C10—C11—N3—O2	−177.3 (4)
C6—C1—C8—O1	−29.5 (6)	S1—C11—N3—O2	2.1 (5)
C2—C1—C8—N1	−32.4 (6)	O4—C19—N4—C20	2.8 (7)
C6—C1—C8—N1	148.8 (4)	C12—C19—N4—C20	−176.2 (4)
N2—C10—C11—N3	179.1 (4)	N5—C20—N4—C19	170.2 (4)
N2—C10—C11—S1	−0.3 (5)	S2—C20—N4—C19	−9.0 (6)
C17—C12—C13—C14	0.0 (7)	N4—C20—N5—C22	−178.9 (4)
C19—C12—C13—C14	−179.2 (4)	S2—C20—N5—C22	0.4 (5)
C12—C13—C14—C15	−1.2 (7)	C21—C22—N5—C20	−0.3 (6)
C13—C14—C15—C16	0.8 (7)	C22—C21—N6—O5	172.6 (4)
C13—C14—C15—C18	−177.6 (4)	S2—C21—N6—O5	−10.3 (6)
C14—C15—C16—C17	0.8 (7)	C22—C21—N6—O6	−7.9 (7)
C18—C15—C16—C17	179.2 (4)	S2—C21—N6—O6	169.2 (3)
C15—C16—C17—C12	−2.0 (7)	C10—C11—S1—C9	0.8 (4)
C13—C12—C17—C16	1.6 (7)	N3—C11—S1—C9	−178.7 (4)
C19—C12—C17—C16	−179.2 (4)	N2—C9—S1—C11	−1.2 (3)
C14—C15—C18—F6	−137.1 (6)	N1—C9—S1—C11	177.2 (4)
C16—C15—C18—F6	44.5 (7)	C22—C21—S2—C20	0.0 (4)
C14—C15—C18—F5	101.7 (6)	N6—C21—S2—C20	−177.4 (4)
C16—C15—C18—F5	−76.7 (6)	N5—C20—S2—C21	−0.3 (4)
C14—C15—C18—F4	−15.3 (7)	N4—C20—S2—C21	179.0 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···N5ⁱ	0.86	2.32	3.044 (5)	142
N1—H1···O3ⁱ	0.86	2.57	3.023 (5)	115
N4—H4···N2ⁱⁱ	0.86	2.18	2.939 (5)	147
N4—H4···O2	0.86	2.62	3.146 (5)	121

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

Experimental details

Crystal data
Chemical formula	C₁₁H₆F₃N₃O₃S
M_r	317.26
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	12.362 (4), 8.946 (3), 23.261 (8)
β (°)	100.762 (4)
V (Å³)	2527.2 (15)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.31
Crystal size (mm)	0.34 × 0.32 × 0.25

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.903, 0.927
No. of measured, independent and observed [I > 2σ(I)] reflections	11671, 4588, 3183
R_int	0.039
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.069, 0.175, 1.06
No. of reflections	4588
No. of parameters	379
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.50, −0.48

Computer programs: APEX2 (Bruker, 2008), SAINT (Bruker, 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···N5ⁱ	0.86	2.32	3.044 (5)	142
N1—H1···O3ⁱ	0.86	2.57	3.023 (5)	115
N4—H4···N2ⁱⁱ	0.86	2.18	2.939 (5)	147
N4—H4···O2	0.86	2.62	3.146 (5)	121

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

Acknowledgements

This study was supported by the earmarked fund for China Agriculture Research System (cars-38) and the program funded by the Basic Scientific Research Funds in Central Agricultural Scientific Research Institutions (1610322013005).

References

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