2,2-Diphenyl-N-{[2-(tri­fluoro­meth­yl)phen­yl]carbamo­thio­yl}acetamide

Yusof, M.S.M.; Razali, N.R.; Arshad, S.; Rahman, A.A.; Razak, I.A.

doi:10.1107/S1600536813018680

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 69| Part 8| August 2013| Pages o1255-o1256

doi:10.1107/S1600536813018680

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2,2-Diphenyl-N-{[2-(trifluoromethyl)phenyl]carbamothioyl}acetamide

Mohd Sukeri Mohd Yusof,^a Nur Rafikah Razali,^a Suhana Arshad,^b ‡ Azhar Abdul Rahman ^b and Ibrahim Abdul Razak ^b ^*§

^aDepartment of Chemical Sciences, Faculty of Science and Technology, Universiti Malaysia Terengganu, Mengabang Telipot, 21030 Kuala Terengganu, Malaysia, and ^bSchool of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
^*Correspondence e-mail: arazaki@usm.my

(Received 12 June 2013; accepted 5 July 2013; online 13 July 2013)

The title molecule, C₂₂H₁₇F₃N₂OS, adopts a trans–cis conformation with respect to the positions of the carbonyl and trifluoromethylbenzene groups against the thiocarbonyl group across the C—N bonds. The molecular structure is stabilized by an intramolecular N—H⋯O hydrogen bond with an S(6) ring motif. The trifluoromethyl-substituted benzene ring forms dihedral angles of 66.05 (9) and 47.19 (9)° with the terminal phenyl rings and is twisted from the O=C—N—(C=S)—N carbonylthiourea plane [maximum deviation = 0.0535 (12) Å], making a dihedral angle of 63.59 (8)°. In the crystal, N—H⋯O and C—H⋯F hydrogen bonds link the molecules into a layer parallel to the bc plane. A C—H⋯π interaction is also observed.

Related literature

For the biological activity of thiourea derivatives, see: Vankatachalam et al. (2001 ). For related structures, see: Yusof, Arshad et al. (2012 ); Yusof, Embong et al. (2012 ); Yusof, Mutalib et al. (2012 ). For hydrogen-bond motifs, see: Bernstein et al. (1995 ). For bond-length data, see: Allen et al. (1987 ). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986 ).

Experimental

Crystal data

C₂₂H₁₇F₃N₂OS
M_r = 414.44
Orthorhombic, P c a 2₁
a = 20.0318 (4) Å
b = 10.2866 (2) Å
c = 9.5351 (2) Å
V = 1964.79 (7) Å³
Z = 4
Mo Kα radiation
μ = 0.21 mm⁻¹
T = 100 K
0.56 × 0.18 × 0.06 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.892, T_max = 0.987
21265 measured reflections
5618 independent reflections
4608 reflections with I > 2σ(I)
R_int = 0.047

Refinement

R[F² > 2σ(F²)] = 0.044
wR(F²) = 0.081
S = 1.02
5618 reflections
270 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.24 e Å⁻³
Δρ_min = −0.25 e Å⁻³
Absolute structure: Flack (1983 ), 2568 Freidel pairs
Flack parameter: 0.01 (6)

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C1–C6 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N1⋯O1	0.96 (3)	1.93 (2)	2.6237 (19)	127 (2)
N2—H1N2⋯O1ⁱ	0.81 (2)	2.04 (2)	2.838 (2)	174 (2)
C9—H9A⋯F1ⁱⁱ	0.95	2.53	3.395 (2)	151
C7—H7A⋯Cg1ⁱⁱⁱ	1.00	2.84	3.7826 (19)	158
Symmetry codes: (i) $[-x+{\script{1\over 2}}, y, z+{\script{1\over 2}}]$ ; (ii) $[-x+{\script{1\over 2}}, y+1, z+{\script{1\over 2}}]$ ; (iii) $[x+{\script{1\over 2}}, -y, z]$ .

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536813018680/is5283sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813018680/is5283Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536813018680/is5283Isup3.cml

checkCIF report

Comment top

Recent studies have shown that thiourea derivatives are potential biologically active agents, such as antimicrobials and HIV inhibitors (Vankatachalam et al., 2001). The molecular structure of the title compound is shown in Fig. 1. The bond lengths (Allen et al., 1987) and angles are within normal ranges and are comparable to the related structures (Yusof, Arshad et al., 2012; Yusof, Embong et al., 2012; Yusof, Mutalib et al., 2012). The molecule adopts a trans-cis configuration with respect to the positions of diphenylmethane and trifluoromethylbenzene (F1–F3/C16–C22) groups, respectively, to the sulfur (S1) atom across the C—N bond. The trifluoromethyl-substituted benzene ring (C16–C21) forms dihedral angles of 66.05 (9) and 47.19 (9)° with the terminal phenyl rings, C1–C6 and C8–C13, respectively. Furthermore, the trifluoromethylbenzene plane (C16–C22) is slightly twisted from the carbonyl thiourea moiety (S1/O1/N1/N2/C15/C14) with a C15—N1—C16—C21 torsion angle of 119.3 (2)°. In the molecule, an intramolecular N2—H1N2···O1 hydrogen bond forms an S(6) graph-set motif (Bernstein et al., 1995).

In the crystal (Fig. 2), molecules are linked into a one-dimensional chain along the c-axis via intermolecular N2—H1N2···O1 hydrogen bonds (Table 1) and further connected into a two dimensional layer parallel to the bc-plane by intermolecular C9—H9A···F1 hydrogen bonds (Table 1). In addition, a C7—H7A···Cg1 (Table 1) interaction is also observed in the crystal structure (Cg1 is the centroid of C1–C6).

Related literature top

For the biological activity of thiourea derivatives, see: Vankatachalam et al. (2001). For related structures, see: Yusof, Arshad et al. (2012); Yusof, Embong et al. (2012); Yusof, Mutalib et al. (2012). For hydrogen-bond motifs, see: Bernstein et al. (1995). For bond-length data, see: Allen et al. (1987). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986).

Experimental top

An acetone (30 ml) solution of 2-triflouroaniline (1.25 g, 8.4 mmol) was added to a round-bottom flask containing 2,2-diphenylacetyl chloride (1.93 g, 8.4 mmol) and ammonium thiocyanate (0.64 g, 8.4 mmol). The mixture was put at reflux for 1.5 H then filtered off and left to evaporate at room temperature. The colourless precipitate obtained was washed with water and cold ethanol. Colourless crystals suitable for X-ray analysis were obtained by recrystallization of the precipitate in acetone.

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of the title compound with atom labels with 50% probability displacement ellipsoids. The dashed line represents the intramolecular hydrogen bond.
	Fig. 2. The crystal packing of the title compound. The H atoms not involved in the intermolecular interactions (dashed lines) have been omitted for clarity.

2,2-Diphenyl-N-{[2-(trifluoromethyl)phenyl]carbamothioyl}acetamide top

Crystal data top

C₂₂H₁₇F₃N₂OS	F(000) = 856
M_r = 414.44	D_x = 1.401 Mg m⁻³
Orthorhombic, Pca2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2ac	Cell parameters from 5325 reflections
a = 20.0318 (4) Å	θ = 2.2–27.2°
b = 10.2866 (2) Å	µ = 0.21 mm⁻¹
c = 9.5351 (2) Å	T = 100 K
V = 1964.79 (7) Å³	Plate, colourless
Z = 4	0.56 × 0.18 × 0.06 mm

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	5618 independent reflections
Radiation source: fine-focus sealed tube	4608 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.047
ϕ and ω scans	θ_max = 30.1°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −27→28
T_min = 0.892, T_max = 0.987	k = −14→14
21265 measured reflections	l = −13→13

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.044	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.081	w = 1/[σ²(F_o²) + (0.0299P)² + 0.2655P] where P = (F_o² + 2F_c²)/3
S = 1.02	(Δ/σ)_max = 0.001
5618 reflections	Δρ_max = 0.24 e Å⁻³
270 parameters	Δρ_min = −0.25 e Å⁻³
2 restraints	Absolute structure: Flack (1983), 2568 Freidel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.01 (6)

Crystal data top

C₂₂H₁₇F₃N₂OS	V = 1964.79 (7) Å³
M_r = 414.44	Z = 4
Orthorhombic, Pca2₁	Mo Kα radiation
a = 20.0318 (4) Å	µ = 0.21 mm⁻¹
b = 10.2866 (2) Å	T = 100 K
c = 9.5351 (2) Å	0.56 × 0.18 × 0.06 mm

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	5618 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	4608 reflections with I > 2σ(I)
T_min = 0.892, T_max = 0.987	R_int = 0.047
21265 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.044	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.081	Δρ_max = 0.24 e Å⁻³
S = 1.02	Δρ_min = −0.25 e Å⁻³
5618 reflections	Absolute structure: Flack (1983), 2568 Freidel pairs
270 parameters	Absolute structure parameter: 0.01 (6)
2 restraints

Special details top

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

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
F1	0.34230 (6)	0.45765 (11)	−0.02227 (17)	0.0418 (4)
F2	0.32081 (5)	0.66244 (10)	−0.02775 (14)	0.0327 (3)
F3	0.29424 (5)	0.54911 (10)	0.15416 (15)	0.0328 (3)
S1	0.35402 (2)	0.73635 (4)	0.50740 (6)	0.02441 (11)
N1	0.36053 (7)	0.78665 (14)	0.2330 (2)	0.0187 (3)
N2	0.28048 (8)	0.90001 (14)	0.3579 (2)	0.0174 (3)
O1	0.27383 (6)	0.95082 (11)	0.12731 (15)	0.0193 (3)
C1	0.14450 (8)	1.10138 (16)	0.0592 (2)	0.0181 (4)
H1A	0.1299	1.0144	0.0731	0.022*
C2	0.12280 (9)	1.16913 (18)	−0.0574 (2)	0.0224 (4)
H2A	0.0944	1.1282	−0.1238	0.027*
C3	0.14277 (9)	1.29838 (18)	−0.0774 (2)	0.0257 (5)
H3A	0.1276	1.3458	−0.1568	0.031*
C4	0.18467 (8)	1.35616 (16)	0.0193 (2)	0.0243 (5)
H4A	0.1982	1.4439	0.0065	0.029*
C5	0.20734 (8)	1.28682 (16)	0.1358 (2)	0.0222 (4)
H5A	0.2365	1.3272	0.2012	0.027*
C6	0.18726 (8)	1.15807 (15)	0.1565 (2)	0.0168 (4)
C7	0.20977 (8)	1.08378 (15)	0.2869 (2)	0.0152 (4)
H7A	0.2368	1.1458	0.3444	0.018*
C8	0.14922 (8)	1.04613 (16)	0.3756 (2)	0.0161 (4)
C9	0.12615 (9)	1.13343 (17)	0.4758 (2)	0.0217 (4)
H9A	0.1498	1.2121	0.4917	0.026*
C10	0.06891 (9)	1.10700 (18)	0.5532 (2)	0.0253 (4)
H10A	0.0533	1.1678	0.6206	0.030*
C11	0.03473 (9)	0.99143 (19)	0.5314 (2)	0.0273 (5)
H11A	−0.0043	0.9727	0.5843	0.033*
C12	0.05759 (9)	0.90365 (18)	0.4329 (2)	0.0240 (5)
H12A	0.0341	0.8246	0.4183	0.029*
C13	0.11465 (9)	0.92994 (16)	0.3548 (2)	0.0201 (4)
H13A	0.1301	0.8689	0.2874	0.024*
C14	0.25639 (8)	0.97102 (14)	0.2475 (2)	0.0148 (3)
C15	0.33231 (8)	0.80792 (16)	0.3580 (2)	0.0176 (4)
C16	0.41583 (8)	0.70043 (16)	0.2104 (2)	0.0185 (4)
C17	0.47773 (9)	0.72797 (17)	0.2680 (2)	0.0216 (4)
H17A	0.4830	0.8010	0.3280	0.026*
C18	0.53209 (9)	0.64879 (18)	0.2380 (2)	0.0260 (5)
H18A	0.5745	0.6681	0.2774	0.031*
C19	0.52477 (9)	0.54208 (18)	0.1511 (3)	0.0295 (5)
H19A	0.5619	0.4874	0.1320	0.035*
C20	0.46349 (9)	0.51515 (18)	0.0922 (3)	0.0269 (5)
H20A	0.4586	0.4424	0.0317	0.032*
C21	0.40852 (9)	0.59409 (16)	0.1208 (2)	0.0213 (4)
C22	0.34224 (9)	0.56611 (17)	0.0566 (3)	0.0261 (5)
H1N2	0.2679 (10)	0.9143 (17)	0.4368 (17)	0.015 (6)*
H1N1	0.3439 (11)	0.823 (2)	0.147 (3)	0.049 (7)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
F1	0.0392 (7)	0.0294 (6)	0.0567 (11)	−0.0032 (5)	−0.0016 (8)	−0.0226 (7)
F2	0.0323 (6)	0.0328 (6)	0.0330 (8)	−0.0032 (5)	−0.0084 (6)	−0.0004 (6)
F3	0.0265 (5)	0.0316 (6)	0.0403 (9)	−0.0078 (4)	0.0048 (6)	−0.0017 (6)
S1	0.0327 (2)	0.02260 (19)	0.0179 (2)	0.00898 (17)	0.0012 (3)	0.0045 (2)
N1	0.0213 (7)	0.0191 (7)	0.0156 (9)	0.0036 (6)	−0.0009 (8)	−0.0003 (7)
N2	0.0215 (7)	0.0200 (7)	0.0107 (9)	0.0040 (6)	0.0024 (8)	−0.0003 (7)
O1	0.0197 (6)	0.0248 (6)	0.0135 (8)	0.0022 (5)	−0.0008 (6)	0.0012 (6)
C1	0.0161 (7)	0.0196 (8)	0.0187 (10)	−0.0002 (6)	0.0020 (8)	0.0020 (8)
C2	0.0202 (8)	0.0273 (9)	0.0196 (11)	0.0014 (7)	−0.0015 (9)	0.0023 (9)
C3	0.0211 (9)	0.0286 (9)	0.0274 (13)	0.0056 (7)	0.0021 (9)	0.0119 (9)
C4	0.0224 (8)	0.0200 (7)	0.0306 (13)	0.0011 (6)	0.0028 (10)	0.0105 (9)
C5	0.0185 (8)	0.0188 (7)	0.0293 (13)	−0.0021 (6)	0.0018 (10)	0.0033 (9)
C6	0.0150 (7)	0.0169 (7)	0.0186 (11)	0.0018 (6)	0.0020 (8)	0.0023 (8)
C7	0.0163 (7)	0.0154 (7)	0.0138 (10)	−0.0015 (6)	−0.0004 (8)	−0.0005 (7)
C8	0.0165 (7)	0.0195 (8)	0.0124 (10)	0.0018 (6)	−0.0008 (8)	0.0021 (7)
C9	0.0228 (8)	0.0226 (7)	0.0196 (12)	0.0038 (6)	−0.0019 (9)	0.0013 (8)
C10	0.0252 (9)	0.0319 (9)	0.0188 (11)	0.0098 (7)	0.0021 (9)	0.0015 (9)
C11	0.0180 (8)	0.0378 (10)	0.0260 (14)	0.0047 (7)	0.0044 (10)	0.0123 (10)
C12	0.0190 (8)	0.0265 (9)	0.0266 (13)	−0.0021 (7)	−0.0007 (9)	0.0081 (9)
C13	0.0188 (8)	0.0209 (8)	0.0205 (11)	0.0003 (6)	−0.0009 (9)	0.0038 (9)
C14	0.0132 (7)	0.0164 (7)	0.0147 (10)	−0.0030 (6)	−0.0007 (8)	0.0026 (8)
C15	0.0199 (8)	0.0142 (7)	0.0187 (10)	−0.0012 (6)	0.0015 (9)	0.0011 (8)
C16	0.0195 (8)	0.0176 (7)	0.0184 (11)	0.0030 (6)	0.0024 (9)	0.0021 (8)
C17	0.0239 (9)	0.0209 (8)	0.0199 (11)	0.0006 (7)	−0.0005 (9)	0.0008 (8)
C18	0.0201 (8)	0.0277 (9)	0.0303 (13)	0.0017 (7)	0.0004 (10)	0.0047 (10)
C19	0.0255 (9)	0.0252 (9)	0.0378 (15)	0.0072 (7)	0.0066 (11)	0.0030 (10)
C20	0.0301 (9)	0.0196 (8)	0.0309 (14)	0.0026 (7)	0.0053 (10)	−0.0042 (9)
C21	0.0231 (8)	0.0162 (7)	0.0247 (12)	−0.0007 (6)	0.0029 (9)	−0.0006 (8)
C22	0.0275 (9)	0.0197 (8)	0.0313 (13)	−0.0021 (7)	0.0027 (10)	−0.0066 (9)

Geometric parameters (Å, º) top

F1—C22	1.345 (2)	C7—C14	1.536 (2)
F2—C22	1.346 (2)	C7—H7A	1.0000
F3—C22	1.349 (2)	C8—C9	1.391 (3)
S1—C15	1.661 (2)	C8—C13	1.395 (2)
N1—C15	1.337 (3)	C9—C10	1.390 (3)
N1—C16	1.435 (2)	C9—H9A	0.9500
N1—H1N1	0.96 (3)	C10—C11	1.388 (3)
N2—C14	1.369 (3)	C10—H10A	0.9500
N2—C15	1.405 (2)	C11—C12	1.382 (3)
N2—H1N2	0.807 (15)	C11—H11A	0.9500
O1—C14	1.216 (2)	C12—C13	1.391 (3)
C1—C2	1.382 (3)	C12—H12A	0.9500
C1—C6	1.391 (3)	C13—H13A	0.9500
C1—H1A	0.9500	C16—C17	1.386 (2)
C2—C3	1.402 (3)	C16—C21	1.395 (3)
C2—H2A	0.9500	C17—C18	1.390 (2)
C3—C4	1.382 (3)	C17—H17A	0.9500
C3—H3A	0.9500	C18—C19	1.383 (3)
C4—C5	1.396 (3)	C18—H18A	0.9500
C4—H4A	0.9500	C19—C20	1.378 (3)
C5—C6	1.398 (2)	C19—H19A	0.9500
C5—H5A	0.9500	C20—C21	1.395 (2)
C6—C7	1.527 (3)	C20—H20A	0.9500
C7—C8	1.529 (2)	C21—C22	1.490 (3)

C15—N1—C16	124.13 (18)	C12—C11—C10	119.86 (18)
C15—N1—H1N1	123.6 (14)	C12—C11—H11A	120.1
C16—N1—H1N1	112.2 (15)	C10—C11—H11A	120.1
C14—N2—C15	128.37 (19)	C11—C12—C13	120.64 (18)
C14—N2—H1N2	120.6 (14)	C11—C12—H12A	119.7
C15—N2—H1N2	110.6 (14)	C13—C12—H12A	119.7
C2—C1—C6	121.25 (16)	C12—C13—C8	119.89 (19)
C2—C1—H1A	119.4	C12—C13—H13A	120.1
C6—C1—H1A	119.4	C8—C13—H13A	120.1
C1—C2—C3	119.90 (18)	O1—C14—N2	122.15 (15)
C1—C2—H2A	120.1	O1—C14—C7	122.26 (17)
C3—C2—H2A	120.1	N2—C14—C7	115.46 (18)
C4—C3—C2	119.35 (19)	N1—C15—N2	114.95 (19)
C4—C3—H3A	120.3	N1—C15—S1	125.53 (14)
C2—C3—H3A	120.3	N2—C15—S1	119.53 (16)
C3—C4—C5	120.61 (16)	C17—C16—C21	119.80 (16)
C3—C4—H4A	119.7	C17—C16—N1	120.32 (16)
C5—C4—H4A	119.7	C21—C16—N1	119.68 (16)
C4—C5—C6	120.18 (18)	C16—C17—C18	119.99 (18)
C4—C5—H5A	119.9	C16—C17—H17A	120.0
C6—C5—H5A	119.9	C18—C17—H17A	120.0
C1—C6—C5	118.69 (17)	C19—C18—C17	120.36 (18)
C1—C6—C7	120.99 (14)	C19—C18—H18A	119.8
C5—C6—C7	120.27 (17)	C17—C18—H18A	119.8
C6—C7—C8	110.06 (13)	C20—C19—C18	119.87 (17)
C6—C7—C14	111.04 (16)	C20—C19—H19A	120.1
C8—C7—C14	115.23 (13)	C18—C19—H19A	120.1
C6—C7—H7A	106.7	C19—C20—C21	120.42 (18)
C8—C7—H7A	106.7	C19—C20—H20A	119.8
C14—C7—H7A	106.7	C21—C20—H20A	119.8
C9—C8—C13	119.07 (17)	C20—C21—C16	119.55 (17)
C9—C8—C7	118.72 (15)	C20—C21—C22	120.68 (17)
C13—C8—C7	122.14 (17)	C16—C21—C22	119.77 (16)
C10—C9—C8	120.82 (17)	F1—C22—F2	106.09 (19)
C10—C9—H9A	119.6	F1—C22—F3	106.16 (14)
C8—C9—H9A	119.6	F2—C22—F3	106.26 (15)
C11—C10—C9	119.71 (18)	F1—C22—C21	112.90 (15)
C11—C10—H10A	120.1	F2—C22—C21	112.79 (15)
C9—C10—H10A	120.1	F3—C22—C21	112.10 (19)

C6—C1—C2—C3	−1.4 (3)	C8—C7—C14—O1	128.74 (18)
C1—C2—C3—C4	0.7 (3)	C6—C7—C14—N2	178.66 (14)
C2—C3—C4—C5	0.3 (3)	C8—C7—C14—N2	−55.4 (2)
C3—C4—C5—C6	−0.6 (3)	C16—N1—C15—N2	177.55 (15)
C2—C1—C6—C5	1.1 (3)	C16—N1—C15—S1	−2.0 (3)
C2—C1—C6—C7	178.57 (16)	C14—N2—C15—N1	−1.1 (3)
C4—C5—C6—C1	−0.1 (3)	C14—N2—C15—S1	178.46 (14)
C4—C5—C6—C7	−177.58 (16)	C15—N1—C16—C17	−65.9 (2)
C1—C6—C7—C8	−60.0 (2)	C15—N1—C16—C21	119.3 (2)
C5—C6—C7—C8	117.41 (17)	C21—C16—C17—C18	−0.8 (3)
C1—C6—C7—C14	68.76 (19)	N1—C16—C17—C18	−175.70 (19)
C5—C6—C7—C14	−113.78 (17)	C16—C17—C18—C19	−0.2 (3)
C6—C7—C8—C9	−88.1 (2)	C17—C18—C19—C20	1.0 (3)
C14—C7—C8—C9	145.37 (17)	C18—C19—C20—C21	−0.7 (3)
C6—C7—C8—C13	88.9 (2)	C19—C20—C21—C16	−0.4 (3)
C14—C7—C8—C13	−37.6 (3)	C19—C20—C21—C22	179.5 (2)
C13—C8—C9—C10	−1.0 (3)	C17—C16—C21—C20	1.1 (3)
C7—C8—C9—C10	176.08 (17)	N1—C16—C21—C20	176.01 (19)
C8—C9—C10—C11	0.8 (3)	C17—C16—C21—C22	−178.75 (18)
C9—C10—C11—C12	−0.3 (3)	N1—C16—C21—C22	−3.9 (3)
C10—C11—C12—C13	0.0 (3)	C20—C21—C22—F1	2.8 (3)
C11—C12—C13—C8	−0.2 (3)	C16—C21—C22—F1	−177.32 (18)
C9—C8—C13—C12	0.7 (3)	C20—C21—C22—F2	−117.5 (2)
C7—C8—C13—C12	−176.30 (18)	C16—C21—C22—F2	62.4 (3)
C15—N2—C14—O1	8.3 (3)	C20—C21—C22—F3	122.6 (2)
C15—N2—C14—C7	−167.60 (16)	C16—C21—C22—F3	−57.5 (2)
C6—C7—C14—O1	2.8 (2)

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C1–C6 ring.

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N1···O1	0.96 (3)	1.93 (2)	2.6237 (19)	127 (2)
N2—H1N2···O1ⁱ	0.81 (2)	2.04 (2)	2.838 (2)	174 (2)
C9—H9A···F1ⁱⁱ	0.95	2.53	3.395 (2)	151
C7—H7A···Cg1ⁱⁱⁱ	1.00	2.84	3.7826 (19)	158

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

Experimental details

Crystal data
Chemical formula	C₂₂H₁₇F₃N₂OS
M_r	414.44
Crystal system, space group	Orthorhombic, Pca2₁
Temperature (K)	100
a, b, c (Å)	20.0318 (4), 10.2866 (2), 9.5351 (2)
V (Å³)	1964.79 (7)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.21
Crystal size (mm)	0.56 × 0.18 × 0.06

Data collection
Diffractometer	Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.892, 0.987
No. of measured, independent and observed [I > 2σ(I)] reflections	21265, 5618, 4608
R_int	0.047
(sin θ/λ)_max (Å⁻¹)	0.705

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.044, 0.081, 1.02
No. of reflections	5618
No. of parameters	270
No. of restraints	2
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.24, −0.25
Absolute structure	Flack (1983), 2568 Freidel pairs
Absolute structure parameter	0.01 (6)

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C1–C6 ring.

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N1···O1	0.96 (3)	1.93 (2)	2.6237 (19)	127 (2)
N2—H1N2···O1ⁱ	0.807 (15)	2.035 (15)	2.838 (2)	174 (2)
C9—H9A···F1ⁱⁱ	0.95	2.53	3.395 (2)	151
C7—H7A···Cg1ⁱⁱⁱ	1.00	2.84	3.7826 (19)	158

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

Footnotes

‡Thomson Reuters ResearcherID: F-9119-2012.

§Thomson Reuters ResearcherID: A-5599-2009.

Acknowledgements

The authors thank the Malaysian Government and Universiti Sains Malaysia (USM) for the USM Short Term Grant, No. 304/PFIZIK/6312078, to conduct this work. SA thanks the Malaysian Government and USM for an Academic Staff Training Scheme Fellowship (ASTS).

References

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Volume 69| Part 8| August 2013| Pages o1255-o1256

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