N-[(4-Carbamoylphen­yl)carbamothio­yl]-2,3,4,5-tetra­fluoro­benzamide

Zhang, L.-D.; Gao, C.; Song, X.-J.; Yu, L.-T.

doi:10.1107/S1600536811005915

organic compounds

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ISSN: 2056-9890

Volume 67| Part 3| March 2011| Page o688

doi:10.1107/S1600536811005915

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N-[(4-Carbamoylphenyl)carbamothioyl]-2,3,4,5-tetrafluorobenzamide

Li-Dan Zhang,^a Chao Gao,^b Xue-Jiao Song ^c and Luo-Ting Yu ^b ^*

^aDepartment of Pharmaceutical and Bioengineering, School of Chemical Engineering, Sichuan University, Chengdu 610065, People's Republic of China, ^bState Key Laboratory of Biotherapy and Cancer Center, West China Hospital, West China Medical School, Sichuan University, Chengdu 610041, People's Republic of China, and ^cWest China School of Pharmacy, Sichuan University, Chengdu 610041, People's Republic of China
^*Correspondence e-mail: yuluot@scu.edu.cn

(Received 14 December 2010; accepted 17 February 2011; online 23 February 2011)

In the title compound, C₁₅H₉F₄N₃O₂S, the N,N′-disubstituted thiourea fragment adopts a cis,trans geometry, stabilized by an intramolecular N—H⋯O hydrogen bond to the carbonyl O atom of the tetrafluorobenzoyl group. The central thiourea group makes dihedral angles of 47.79 (7) and 35.54 (8)° with the two aromatic rings. In the crystal, molecules are linked via N—H⋯O and N—H⋯S hydrogen bonds into two-dimensional polymeric structures parallel to (100). In turn, π–π stacking interactions between tetrafluorobenzene and benzene units [centroid–centroid distance = 3.996 (10) Å; dihedral angle = 13.60 (8)°] organize these two-dimensional assemblies into a three-dimensional framework.

Related literature

For the biological activity of thiourea derivatives, see: Zeng et al. (2003 ); Saeed et al. (2010 ). For the synthesis of thiourea derivatives, see: Nosova et al. (2007 ). For related structures, see: Saeed et al. (2008 , 2009 ).

Experimental

Crystal data

C₁₅H₉F₄N₃O₂S
M_r = 371.31
Monoclinic, P 2₁ /c
a = 7.4246 (3) Å
b = 20.3368 (7) Å
c = 9.8954 (4) Å
β = 95.554 (3)°
V = 1487.12 (9) Å³
Z = 4
Mo Kα radiation
μ = 0.28 mm⁻¹
T = 294 K
0.38 × 0.30 × 0.26 mm

Data collection

Oxford Diffraction Xcalibur E CCD diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2006 $[Oxford Diffraction (2006). CrysAlis PRO. Oxford Diffraction Ltd, Abingdon, England.]$ ) T_min = 0.860, T_max = 1.0
6598 measured reflections
3031 independent reflections
2263 reflections with I > 2σ(I)
R_int = 0.014

Refinement

R[F² > 2σ(F²)] = 0.036
wR(F²) = 0.103
S = 1.13
3031 reflections
226 parameters
H-atom parameters constrained
Δρ_max = 0.31 e Å⁻³
Δρ_min = −0.34 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1B⋯S1ⁱ	0.86	2.69	3.4861 (16)	155
N1—H1A⋯O1ⁱⁱ	0.86	2.23	2.8654 (17)	130
N2—H2⋯O2	0.86	1.97	2.6708 (18)	138
N3—H3⋯O1ⁱⁱⁱ	0.86	2.09	2.9062 (18)	157
Symmetry codes: (i) $[-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) $[x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ ; (iii) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: CrysAlis PRO (Oxford Diffraction, 2006 $[Oxford Diffraction (2006). CrysAlis PRO. Oxford Diffraction Ltd, Abingdon, England.]$ ); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: OLEX2 (Dolomanov et al., 2009 ) and Mercury (Macrae et al., 2006 ); software used to prepare material for publication: OLEX2.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811005915/gk2335sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811005915/gk2335Isup2.hkl

checkCIF report

Comment top

N-(4-Carbamoylphenylcarbamothioyl)-2,3,4,5-tetrafluorobenzamide derivatives are of great importance owing to their interesting biological properties (Zeng et al., 2003; Saeed et al., 2010). The title compound is one of the key intermediates in our synthetic route to antiviral drugs. We report here its crystal structure.

In the title compound, C₁₅H₉F₄N₃O₂S, (Fig.1), the cis,trans geometry of the thiourea moiety is stabilized by intramolecular N2—H2···O2 and N3—H3···F1 hydrogen bonds. The central thiourea group makes dihedral angles of 47.79 (7) and 35.54 (8)° with the benzamide unit and the fluorobenzene ring, respectively. A combination of intermolecular π–π stacking interactions, N—H···O, N—H···F and N—H···S hydrogen bonds helps to stabilize the crystal structure (Table 1 and Fig.2).

Related literature top

For the biological activity of thiourea derivatives, see: Zeng et al. (2003); Saeed et al. (2010). For the synthesis of thiourea derivatives, see: Nosova et al. (2007). For related structures, see: Saeed et al. (2008, 2009).

Experimental top

A solution of 0.23 g (3 mmol) of ammonium thiocyanate in 7 ml of acetonitrile was added to a solution of 0.64 g (3 mmol) of 2,3,4,5-tetrafluorobenzoyl chloride in 2.5 ml of toluene. The mixture was heated for 5 min at 40°C and filtered from ammonium chloride, the filtrate was added to a solution of 0.32 g (3 mmol) of 4-aminobenzamide in 5 ml of acetonitrile, the mixture was stirred for 2 h at room temperature and evaporated, and the residue was washed with ethanol and recrystallized from ethanol. Yield 0.91 g (82%). Crystals suitable for X-ray analysis were obtained by slow evaporation from ethyl acetate solution.

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2006); cell refinement: CrysAlis PRO (Oxford Diffraction, 2006); data reduction: CrysAlis PRO (Oxford Diffraction, 2006); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: OLEX2 (Dolomanov et al., 2009) and Mercury (Macrae et al., 2006); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

Figures top

	Fig. 1. The molecular structure of the title compound, with displacement ellipsoids drawn at the 30% probability level.
	Fig. 2. A packing diagram of the title compound, showing classical hydrogen bonds of N1—H1A···O1, N2—H2···O2 and N3—H3···O1 as green dashed lines.

N-[(4-Carbamoylphenyl)carbamothioyl]-2,3,4,5-tetrafluorobenzamide top

Crystal data top

C₁₅H₉F₄N₃O₂S	F(000) = 752
M_r = 371.31	D_x = 1.658 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.7107 Å
Hall symbol: -P 2ybc	Cell parameters from 3669 reflections
a = 7.4246 (3) Å	θ = 3.3–29.2°
b = 20.3368 (7) Å	µ = 0.28 mm⁻¹
c = 9.8954 (4) Å	T = 294 K
β = 95.554 (3)°	Block, colourless
V = 1487.12 (9) Å³	0.38 × 0.30 × 0.26 mm
Z = 4

Data collection top

Oxford Diffraction Xcalibur E CCD diffractometer	3031 independent reflections
Radiation source: fine-focus sealed tube	2263 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.014
Detector resolution: 16.0874 pixels mm^-1	θ_max = 26.4°, θ_min = 3.4°
ω scans	h = −9→9
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2006)	k = −25→21
T_min = 0.860, T_max = 1.0	l = −11→12
6598 measured reflections

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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.103	H-atom parameters constrained
S = 1.13	w = 1/[σ²(F_o²) + (0.056P)²] where P = (F_o² + 2F_c²)/3
3031 reflections	(Δ/σ)_max < 0.001
226 parameters	Δρ_max = 0.31 e Å⁻³
0 restraints	Δρ_min = −0.34 e Å⁻³

Crystal data top

C₁₅H₉F₄N₃O₂S	V = 1487.12 (9) Å³
M_r = 371.31	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 7.4246 (3) Å	µ = 0.28 mm⁻¹
b = 20.3368 (7) Å	T = 294 K
c = 9.8954 (4) Å	0.38 × 0.30 × 0.26 mm
β = 95.554 (3)°

Data collection top

Oxford Diffraction Xcalibur E CCD diffractometer	3031 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2006)	2263 reflections with I > 2σ(I)
T_min = 0.860, T_max = 1.0	R_int = 0.014
6598 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.036	0 restraints
wR(F²) = 0.103	H-atom parameters constrained
S = 1.13	Δρ_max = 0.31 e Å⁻³
3031 reflections	Δρ_min = −0.34 e Å⁻³
226 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
S1	0.41600 (7)	0.40876 (2)	0.28889 (6)	0.05125 (18)
F	0.98701 (18)	0.10215 (6)	−0.07009 (12)	0.0623 (4)
F1	0.66951 (14)	0.21050 (5)	0.34645 (9)	0.0445 (3)
F2	0.72451 (16)	0.08149 (5)	0.33952 (12)	0.0543 (3)
F3	0.87569 (17)	0.02540 (5)	0.12899 (13)	0.0635 (4)
O1	0.66762 (17)	0.73716 (6)	0.33958 (11)	0.0386 (3)
O2	0.91223 (18)	0.33325 (6)	0.09914 (14)	0.0471 (3)
N1	0.7405 (2)	0.75363 (7)	0.12865 (14)	0.0434 (4)
H1B	0.7340	0.7956	0.1382	0.052*
H1A	0.7683	0.7373	0.0532	0.052*
N2	0.7175 (2)	0.43553 (7)	0.17165 (14)	0.0390 (4)
H2	0.8046	0.4200	0.1300	0.047*
N3	0.64026 (19)	0.32604 (7)	0.18763 (14)	0.0356 (3)
H3	0.5580	0.2981	0.2036	0.043*
C1	0.7076 (2)	0.71401 (8)	0.23066 (16)	0.0304 (4)
C2	0.7164 (2)	0.64135 (8)	0.21097 (16)	0.0286 (4)
C3	0.7548 (3)	0.61151 (9)	0.09123 (18)	0.0392 (4)
H3A	0.7823	0.6372	0.0182	0.047*
C4	0.7524 (3)	0.54374 (9)	0.07970 (18)	0.0425 (5)
H4	0.7771	0.5241	−0.0013	0.051*
C5	0.7133 (2)	0.50499 (8)	0.18833 (17)	0.0343 (4)
C6	0.6795 (2)	0.53412 (8)	0.30877 (17)	0.0367 (4)
H6	0.6566	0.5083	0.3828	0.044*
C7	0.6796 (2)	0.60191 (8)	0.31958 (16)	0.0329 (4)
H7	0.6546	0.6214	0.4007	0.039*
C8	0.6006 (2)	0.39170 (8)	0.21371 (17)	0.0345 (4)
C9	0.7920 (2)	0.30012 (9)	0.14025 (17)	0.0338 (4)
C10	0.8043 (2)	0.22623 (8)	0.14010 (16)	0.0315 (4)
C11	0.8887 (2)	0.19686 (9)	0.03581 (18)	0.0369 (4)
H11	0.9315	0.2228	−0.0316	0.044*
C12	0.9089 (2)	0.13022 (9)	0.03208 (19)	0.0410 (4)
C13	0.8521 (3)	0.09051 (8)	0.1325 (2)	0.0414 (5)
C14	0.7735 (2)	0.11852 (8)	0.23825 (18)	0.0369 (4)
C15	0.7476 (2)	0.18583 (8)	0.24020 (16)	0.0326 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0543 (3)	0.0289 (3)	0.0750 (4)	0.0028 (2)	0.0295 (3)	−0.0031 (2)
F	0.0717 (9)	0.0532 (7)	0.0638 (8)	0.0202 (6)	0.0162 (6)	−0.0171 (6)
F1	0.0550 (7)	0.0402 (6)	0.0394 (6)	0.0026 (5)	0.0093 (5)	0.0001 (5)
F2	0.0617 (8)	0.0366 (6)	0.0643 (7)	−0.0022 (5)	0.0052 (6)	0.0184 (5)
F3	0.0688 (8)	0.0237 (6)	0.0975 (10)	0.0083 (5)	0.0051 (7)	−0.0067 (6)
O1	0.0568 (8)	0.0293 (7)	0.0305 (6)	0.0036 (6)	0.0085 (6)	−0.0027 (5)
O2	0.0453 (8)	0.0312 (7)	0.0677 (9)	−0.0037 (6)	0.0199 (7)	0.0007 (6)
N1	0.0702 (11)	0.0250 (8)	0.0374 (8)	−0.0013 (7)	0.0174 (8)	0.0019 (7)
N2	0.0480 (9)	0.0228 (7)	0.0488 (9)	−0.0001 (7)	0.0181 (7)	−0.0001 (7)
N3	0.0392 (8)	0.0215 (7)	0.0481 (9)	0.0008 (6)	0.0145 (7)	0.0009 (6)
C1	0.0333 (9)	0.0274 (9)	0.0303 (9)	0.0002 (7)	0.0031 (7)	0.0003 (7)
C2	0.0310 (9)	0.0245 (9)	0.0303 (8)	0.0002 (7)	0.0028 (7)	0.0005 (7)
C3	0.0559 (12)	0.0280 (9)	0.0359 (10)	−0.0041 (8)	0.0166 (9)	0.0013 (8)
C4	0.0614 (12)	0.0293 (10)	0.0398 (10)	−0.0009 (9)	0.0206 (9)	−0.0057 (8)
C5	0.0409 (10)	0.0213 (9)	0.0416 (10)	−0.0004 (7)	0.0075 (8)	0.0002 (7)
C6	0.0509 (11)	0.0273 (9)	0.0319 (9)	−0.0022 (8)	0.0037 (8)	0.0056 (7)
C7	0.0432 (10)	0.0288 (9)	0.0269 (8)	−0.0004 (7)	0.0042 (7)	−0.0007 (7)
C8	0.0434 (10)	0.0233 (9)	0.0371 (9)	0.0023 (7)	0.0060 (8)	0.0010 (7)
C9	0.0368 (10)	0.0271 (9)	0.0377 (9)	0.0016 (7)	0.0045 (7)	0.0004 (7)
C10	0.0310 (9)	0.0252 (9)	0.0380 (9)	0.0018 (7)	0.0015 (7)	−0.0003 (7)
C11	0.0342 (9)	0.0341 (10)	0.0426 (10)	0.0040 (8)	0.0043 (8)	0.0013 (8)
C12	0.0387 (10)	0.0364 (10)	0.0475 (11)	0.0104 (8)	0.0022 (8)	−0.0113 (9)
C13	0.0389 (10)	0.0221 (9)	0.0612 (12)	0.0040 (8)	−0.0061 (9)	−0.0046 (9)
C14	0.0350 (10)	0.0275 (9)	0.0469 (10)	−0.0027 (7)	−0.0032 (8)	0.0060 (8)
C15	0.0296 (9)	0.0313 (9)	0.0366 (9)	0.0018 (7)	0.0022 (7)	−0.0011 (8)

Geometric parameters (Å, º) top

S1—C8	1.6583 (18)	C2—C7	1.389 (2)
F—C12	1.341 (2)	C3—H3A	0.9300
F1—C15	1.3458 (18)	C3—C4	1.383 (2)
F2—C14	1.332 (2)	C4—H4	0.9300
F3—C13	1.3365 (18)	C4—C5	1.386 (2)
O1—C1	1.2383 (18)	C5—C6	1.376 (2)
O2—C9	1.219 (2)	C6—H6	0.9300
N1—H1B	0.8600	C6—C7	1.383 (2)
N1—H1A	0.8600	C7—H7	0.9300
N1—C1	1.333 (2)	C9—C10	1.505 (2)
N2—H2	0.8600	C10—C11	1.393 (2)
N2—C5	1.423 (2)	C10—C15	1.384 (2)
N2—C8	1.338 (2)	C11—H11	0.9300
N3—H3	0.8600	C11—C12	1.364 (2)
N3—C8	1.397 (2)	C12—C13	1.378 (3)
N3—C9	1.367 (2)	C13—C14	1.370 (3)
C1—C2	1.493 (2)	C14—C15	1.383 (2)
C2—C3	1.385 (2)

F—C12—C11	119.99 (18)	C4—C3—H3A	119.8
F—C12—C13	118.62 (16)	C4—C5—N2	117.77 (15)
F1—C15—C10	121.45 (14)	C5—N2—H2	116.5
F1—C15—C14	116.81 (15)	C5—C4—H4	119.8
F2—C14—C13	120.47 (15)	C5—C6—H6	120.1
F2—C14—C15	120.04 (16)	C5—C6—C7	119.84 (15)
F3—C13—C12	120.80 (18)	C6—C5—N2	122.40 (15)
F3—C13—C14	119.87 (18)	C6—C5—C4	119.77 (15)
O1—C1—N1	120.43 (15)	C6—C7—C2	120.96 (15)
O1—C1—C2	120.47 (14)	C6—C7—H7	119.5
O2—C9—N3	123.76 (16)	C7—C2—C1	117.15 (14)
O2—C9—C10	120.32 (15)	C7—C6—H6	120.1
N1—C1—C2	119.09 (14)	C8—N2—H2	116.5
H1B—N1—H1A	120.0	C8—N2—C5	127.09 (15)
N2—C8—S1	126.10 (13)	C8—N3—H3	115.6
N2—C8—N3	115.14 (15)	C9—N3—H3	115.6
N3—C8—S1	118.75 (12)	C9—N3—C8	128.85 (14)
N3—C9—C10	115.92 (14)	C10—C11—H11	119.9
C1—N1—H1B	120.0	C11—C10—C9	117.41 (15)
C1—N1—H1A	120.0	C11—C12—C13	121.38 (17)
C2—C3—H3A	119.8	C12—C11—C10	120.29 (17)
C2—C7—H7	119.5	C12—C11—H11	119.9
C3—C2—C1	124.10 (15)	C13—C14—C15	119.49 (16)
C3—C2—C7	118.74 (15)	C14—C13—C12	119.32 (15)
C3—C4—H4	119.8	C14—C15—C10	121.71 (15)
C3—C4—C5	120.31 (16)	C15—C10—C9	124.72 (15)
C4—C3—C2	120.34 (16)	C15—C10—C11	117.75 (15)

F—C12—C13—F3	0.6 (3)	C5—N2—C8—N3	−178.02 (15)
F—C12—C13—C14	179.40 (16)	C5—C6—C7—C2	−1.1 (3)
F2—C14—C15—F1	−1.0 (2)	C7—C2—C3—C4	1.4 (3)
F2—C14—C15—C10	177.00 (15)	C8—N2—C5—C4	−138.63 (19)
F3—C13—C14—F2	1.7 (3)	C8—N2—C5—C6	44.1 (3)
F3—C13—C14—C15	−179.20 (15)	C8—N3—C9—O2	−8.1 (3)
O1—C1—C2—C3	178.02 (16)	C8—N3—C9—C10	172.27 (16)
O1—C1—C2—C7	−0.5 (2)	C9—N3—C8—S1	−172.62 (14)
O2—C9—C10—C11	−33.5 (2)	C9—N3—C8—N2	8.7 (3)
O2—C9—C10—C15	142.48 (18)	C9—C10—C11—C12	178.10 (15)
N1—C1—C2—C3	−0.9 (3)	C9—C10—C15—F1	2.2 (2)
N1—C1—C2—C7	−179.44 (15)	C9—C10—C15—C14	−175.74 (15)
N2—C5—C6—C7	179.11 (16)	C10—C11—C12—F	178.65 (16)
N3—C9—C10—C11	146.16 (16)	C10—C11—C12—C13	−2.0 (3)
N3—C9—C10—C15	−37.9 (2)	C11—C10—C15—F1	178.11 (14)
C1—C2—C3—C4	−177.14 (16)	C11—C10—C15—C14	0.2 (2)
C1—C2—C7—C6	178.11 (16)	C11—C12—C13—F3	−178.74 (16)
C2—C3—C4—C5	−0.6 (3)	C11—C12—C13—C14	0.1 (3)
C3—C2—C7—C6	−0.5 (3)	C12—C13—C14—F2	−177.14 (15)
C3—C4—C5—N2	−178.38 (17)	C12—C13—C14—C15	2.0 (3)
C3—C4—C5—C6	−1.0 (3)	C13—C14—C15—F1	179.87 (15)
C4—C5—C6—C7	1.9 (3)	C13—C14—C15—C10	−2.1 (3)
C5—N2—C8—S1	3.4 (3)	C15—C10—C11—C12	1.9 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1B···S1ⁱ	0.86	2.69	3.4861 (16)	155
N1—H1A···O1ⁱⁱ	0.86	2.23	2.8654 (17)	130
N2—H2···O2	0.86	1.97	2.6708 (18)	138
N3—H3···F1	0.86	2.37	2.8234 (17)	113
N3—H3···O1ⁱⁱⁱ	0.86	2.09	2.9062 (18)	157

Symmetry codes: (i) −x+1, y+1/2, −z+1/2; (ii) x, −y+3/2, z−1/2; (iii) −x+1, y−1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₅H₉F₄N₃O₂S
M_r	371.31
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	294
a, b, c (Å)	7.4246 (3), 20.3368 (7), 9.8954 (4)
β (°)	95.554 (3)
V (Å³)	1487.12 (9)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.28
Crystal size (mm)	0.38 × 0.30 × 0.26

Data collection
Diffractometer	Oxford Diffraction Xcalibur E CCD diffractometer
Absorption correction	Multi-scan (CrysAlis PRO; Oxford Diffraction, 2006)
T_min, T_max	0.860, 1.0
No. of measured, independent and observed [I > 2σ(I)] reflections	6598, 3031, 2263
R_int	0.014
(sin θ/λ)_max (Å⁻¹)	0.625

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.036, 0.103, 1.13
No. of reflections	3031
No. of parameters	226
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.31, −0.34

Computer programs: CrysAlis PRO (Oxford Diffraction, 2006), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), OLEX2 (Dolomanov et al., 2009) and Mercury (Macrae et al., 2006), OLEX2 (Dolomanov et al., 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1B···S1ⁱ	0.86	2.69	3.4861 (16)	155
N1—H1A···O1ⁱⁱ	0.86	2.23	2.8654 (17)	130
N2—H2···O2	0.86	1.97	2.6708 (18)	138
N3—H3···F1	0.86	2.37	2.8234 (17)	113
N3—H3···O1ⁱⁱⁱ	0.86	2.09	2.9062 (18)	157

Symmetry codes: (i) −x+1, y+1/2, −z+1/2; (ii) x, −y+3/2, z−1/2; (iii) −x+1, y−1/2, −z+1/2.

Acknowledgements

We thank the Analytical and Testing Center of Sichuan University for the X-ray measurements.

References

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