4-(5-Phenyl-3-trifluoro­meth­yl-1H-pyrazol-1-­yl)benzene­sulfonamide

Asiri, A.M.; Al-Youbi, A.O.; Faidallah, H.M.; Ng, S.W.; Tiekink, E.R.T.

doi:10.1107/S1600536811033435

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 67| Part 9| September 2011| Page o2424

doi:10.1107/S1600536811033435

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4-(5-Phenyl-3-trifluoromethyl-1H-pyrazol-1-yl)benzenesulfonamide

Abdullah M. Asiri,^a,^b ‡ Abdulrahman O. Al-Youbi,^a Hassan M. Faidallah,^a Seik Weng Ng ^c,^a and Edward R. T. Tiekink ^c ^*

^aChemistry Department, Faculty of Science, King Abdulaziz University, PO Box 80203, Jeddah, Saudi Arabia, ^bThe Center of Excellence for Advanced Materials Research, King Abdulaziz University, Jeddah, PO Box 80203, Saudi Arabia, and ^cDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: edward.tiekink@gmail.com

(Received 16 August 2011; accepted 17 August 2011; online 27 August 2011)

Significant twists between the aromatic rings are evident in the structure of the title compound, C₁₆H₁₂F₃N₃O₂S. With reference to the pyrazole plane, the N- and C-bound benzene rings form dihedral angles of 57.12 (11) and 29.75 (11)°, respectively. The dihedral angle between the benzene rings is 52.82 (11)°. The presence of N—H⋯O(sulfonamide) and N—H⋯N(pyrazole) hydrogen bonds lead to supramolecular tubes along the b-axis direction. These are connected into layers via C—H⋯O interactions involving a bifurcated O atom (not involved in the N—H⋯O hydrogen bonding). Layers stack along the a-axis direction.

Related literature

For background to the biological applications of related species, see: Faidallah et al. (2007 ); Al-Saadi et al. (2008 ). For the crystal structure of a related species, see: Dev et al. (1999 ).

Experimental

Crystal data

C₁₆H₁₂F₃N₃O₂S
M_r = 367.35
Monoclinic, P 2₁ /c
a = 16.2430 (7) Å
b = 4.9461 (2) Å
c = 21.2383 (8) Å
β = 111.231 (5)°
V = 1590.47 (11) Å³
Z = 4
Mo Kα radiation
μ = 0.25 mm⁻¹
T = 100 K
0.40 × 0.10 × 0.05 mm

Data collection

Agilent SuperNova Dual diffractometer with an Atlas detector
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010 ) T_min = 0.735, T_max = 1.000
7901 measured reflections
3560 independent reflections
2876 reflections with I > 2σ(I)
R_int = 0.031

Refinement

R[F² > 2σ(F²)] = 0.043
wR(F²) = 0.113
S = 1.06
3560 reflections
234 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.34 e Å⁻³
Δρ_min = −0.49 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H1⋯O1ⁱ	0.84 (3)	2.14 (3)	2.911 (2)	153 (2)
N3—H2⋯N2ⁱⁱ	0.87 (2)	2.21 (3)	3.049 (3)	164 (2)
C9—H9⋯O2ⁱⁱⁱ	0.95	2.49	3.376 (3)	155
C16—H16⋯O2^iv	0.95	2.55	3.137 (2)	120
Symmetry codes: (i) x, y-1, z; (ii) -x+1, -y+1, -z+1; (iii) $[-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iv) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: CrysAlis PRO (Agilent, 2010); 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: ORTEP-3 (Farrugia, 1997 ) and DIAMOND (Brandenburg, 2006 ); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811033435/hg5083sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811033435/hg5083Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811033435/hg5083Isup3.cml

checkCIF report

Comment top

The crystallographic study of the title compound, (I), which is related to the anti-inflammatory drug, Celecoxib (Dev et al., 1999), was motivated by the recent reports of the biological activities exhibited by related pyrazole compounds (Faidallah et al., 2007; Al-Saadi et al., 2008).

Significant twists are evident in the molecule of (I), Fig. 1. With reference to the pyrazole (N1,N2,C2—C4) plane (r.m.s. deviation = 0,003 Å), the N-bound benzene ring (C11–C16) forms a dihedral angle of 57.12 (11) ° whereas the C-bound benzene ring (C5–C10) forms a dihedral angle of 29.75 (11) °; the dihedral angle formed between the two benzene rings is 52.82 (11) °. The orientations of the benzene rings in (I) differ from those in Celecoxib (Dev et al., 1999), the 4-methylphenyl derivative, with the dihedral angles formed between the N– and C-bound benzene rings and the pyrazole plane being 86.00 (12) and 15.25 (13) °, respectively.

Supramolecular tubes along the b axis feature in the crystal packing, Fig. 2. These are stabilized by amino-H hydrogen bonds to the pyrazole-N and to one of the sulfonamide-O atoms, Table 1. Tubes are linked into layers in the bc plane by C—H···O interactions whereby the sulfonamide-O2 atom is bifurcated, Table 1 and Fig. 3. Layers stack along the a axis, Fig. 4.

Related literature top

For background to the biological applications of related species, see: Faidallah et al. (2007); Al-Saadi et al. (2008). For the crystal structure of a related species, see: Dev et al. (1999).

Experimental top

A solution of 4,4,4-trifluoro-1-phenyl-1,3-butanedione (2.01 g, 10 mmol) in ethanol (50 ml) was refluxed with 4-hydrazinobenzenesulfonamide hydrochloride (2.2 g, 10 mmol) for 4 h, cooled and diluted with water. The precipitated crude product was filtered and recrystallized from ethanol as colourless crystals; M.pt. 431–433 K.

Computing details top

Data collection: CrysAlis PRO (Agilent, 2010); cell refinement: CrysAlis PRO (Agilent, 2010); data reduction: CrysAlis PRO (Agilent, 2010); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2006); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

	Fig. 1. The molecular structure of (I) showing the atom-labelling scheme and displacement ellipsoids at the 50% probability level.
	Fig. 2. Supramolecular tube aligned along the b axis in (I) mediated by N—H···O and N—H···N hydrogen bonds shown as orange and blue dashed lines, respectively.
	Fig. 3. A view in projection down the a axis of the unit-cell contents of (I). The N—H···O and N—H···N hydrogen bonds and C—H···O interactions are shown as orange, blue and purple dashed lines, respectively.
	Fig. 4. A view in projection down the b axis of the unit-cell contents of (I) highlighting the stacking of layers along the a direction. The N—H···O and N—H···N hydrogen bonds and C—H···O interactions are shown as orange, blue and purple dashed lines, respectively.

4-(5-Phenyl-3-trifluoromethyl-1H-pyrazol-1-yl)benzenesulfonamide top

Crystal data top

C₁₆H₁₂F₃N₃O₂S	F(000) = 752
M_r = 367.35	D_x = 1.534 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3338 reflections
a = 16.2430 (7) Å	θ = 2.5–29.3°
b = 4.9461 (2) Å	µ = 0.25 mm⁻¹
c = 21.2383 (8) Å	T = 100 K
β = 111.231 (5)°	Prism, colourless
V = 1590.47 (11) Å³	0.40 × 0.10 × 0.05 mm
Z = 4

Data collection top

Agilent SuperNova Dual diffractometer with an Atlas detector	3560 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	2876 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.031
Detector resolution: 10.4041 pixels mm^-1	θ_max = 27.5°, θ_min = 2.7°
ω scans	h = −16→21
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	k = −6→4
T_min = 0.735, T_max = 1.000	l = −27→27
7901 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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.113	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ²(F_o²) + (0.0453P)² + 1.0489P] where P = (F_o² + 2F_c²)/3
3560 reflections	(Δ/σ)_max < 0.001
234 parameters	Δρ_max = 0.34 e Å⁻³
0 restraints	Δρ_min = −0.49 e Å⁻³

Crystal data top

C₁₆H₁₂F₃N₃O₂S	V = 1590.47 (11) Å³
M_r = 367.35	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 16.2430 (7) Å	µ = 0.25 mm⁻¹
b = 4.9461 (2) Å	T = 100 K
c = 21.2383 (8) Å	0.40 × 0.10 × 0.05 mm
β = 111.231 (5)°

Data collection top

Agilent SuperNova Dual diffractometer with an Atlas detector	3560 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	2876 reflections with I > 2σ(I)
T_min = 0.735, T_max = 1.000	R_int = 0.031
7901 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.043	0 restraints
wR(F²) = 0.113	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	Δρ_max = 0.34 e Å⁻³
3560 reflections	Δρ_min = −0.49 e Å⁻³
234 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	0.38822 (3)	0.81404 (10)	0.32626 (2)	0.01565 (14)
F1	0.90203 (11)	0.1680 (3)	0.69086 (6)	0.0425 (4)
F2	0.94604 (9)	−0.1249 (3)	0.63638 (7)	0.0399 (4)
F3	0.81737 (9)	−0.1604 (3)	0.64239 (8)	0.0432 (4)
O1	0.37971 (9)	1.0737 (3)	0.35369 (8)	0.0244 (4)
O2	0.38267 (9)	0.7931 (3)	0.25777 (7)	0.0231 (3)
N1	0.74390 (11)	0.3994 (3)	0.49401 (8)	0.0156 (4)
N2	0.75444 (11)	0.2540 (4)	0.55074 (8)	0.0177 (4)
N3	0.31318 (11)	0.6258 (4)	0.33572 (9)	0.0164 (4)
H1	0.3186 (17)	0.461 (6)	0.3280 (12)	0.030 (7)*
H2	0.3050 (15)	0.658 (5)	0.3732 (12)	0.020 (6)*
C1	0.87573 (14)	0.0151 (5)	0.63544 (11)	0.0243 (5)
C2	0.83889 (13)	0.1780 (4)	0.57227 (10)	0.0179 (4)
C3	0.88288 (13)	0.2711 (4)	0.53112 (10)	0.0183 (4)
H3	0.9429	0.2415	0.5367	0.022*
C4	0.82048 (13)	0.4154 (4)	0.48055 (10)	0.0163 (4)
C5	0.82969 (13)	0.5586 (4)	0.42273 (9)	0.0159 (4)
C6	0.89089 (13)	0.4628 (4)	0.39583 (10)	0.0195 (4)
H6	0.9266	0.3111	0.4160	0.023*
C7	0.90027 (14)	0.5854 (5)	0.34033 (10)	0.0225 (5)
H7	0.9422	0.5181	0.3226	0.027*
C8	0.84853 (14)	0.8061 (4)	0.31056 (10)	0.0224 (5)
H8	0.8542	0.8885	0.2719	0.027*
C9	0.78859 (14)	0.9066 (4)	0.33714 (11)	0.0229 (5)
H9	0.7532	1.0587	0.3168	0.027*
C10	0.77983 (14)	0.7863 (4)	0.39346 (10)	0.0201 (4)
H10	0.7397	0.8595	0.4122	0.024*
C11	0.65665 (12)	0.4914 (4)	0.45432 (9)	0.0151 (4)
C12	0.61316 (15)	0.6612 (5)	0.48304 (11)	0.0324 (6)
H12	0.6395	0.7133	0.5291	0.039*
C13	0.52997 (16)	0.7552 (6)	0.44350 (12)	0.0372 (7)
H13	0.4985	0.8704	0.4627	0.045*
C14	0.49304 (12)	0.6820 (4)	0.37671 (10)	0.0157 (4)
C15	0.53662 (14)	0.5093 (4)	0.34853 (10)	0.0207 (5)
H15	0.5103	0.4580	0.3024	0.025*
C16	0.61907 (14)	0.4107 (4)	0.38786 (10)	0.0209 (4)
H16	0.6494	0.2889	0.3692	0.025*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0135 (2)	0.0142 (3)	0.0179 (2)	0.00119 (19)	0.00409 (19)	0.00217 (18)
F1	0.0559 (10)	0.0483 (9)	0.0155 (6)	0.0101 (8)	0.0035 (6)	0.0034 (6)
F2	0.0336 (8)	0.0494 (9)	0.0404 (8)	0.0254 (7)	0.0179 (7)	0.0220 (7)
F3	0.0308 (8)	0.0513 (10)	0.0446 (9)	−0.0026 (7)	0.0104 (7)	0.0283 (7)
O1	0.0196 (8)	0.0133 (7)	0.0360 (9)	0.0023 (6)	0.0051 (7)	−0.0020 (6)
O2	0.0185 (7)	0.0320 (9)	0.0189 (7)	0.0016 (7)	0.0068 (6)	0.0080 (6)
N1	0.0152 (8)	0.0185 (9)	0.0130 (8)	0.0028 (7)	0.0050 (6)	0.0008 (7)
N2	0.0190 (9)	0.0194 (9)	0.0143 (8)	0.0009 (7)	0.0056 (7)	0.0017 (7)
N3	0.0170 (9)	0.0144 (9)	0.0187 (9)	0.0009 (7)	0.0075 (7)	−0.0001 (7)
C1	0.0202 (11)	0.0282 (12)	0.0247 (11)	0.0059 (9)	0.0083 (9)	0.0065 (9)
C2	0.0174 (10)	0.0186 (10)	0.0167 (9)	0.0034 (8)	0.0048 (8)	0.0006 (8)
C3	0.0147 (10)	0.0214 (10)	0.0187 (10)	0.0024 (8)	0.0061 (8)	−0.0001 (8)
C4	0.0136 (9)	0.0174 (10)	0.0175 (9)	0.0005 (8)	0.0053 (8)	−0.0026 (8)
C5	0.0137 (9)	0.0180 (10)	0.0145 (9)	−0.0032 (8)	0.0034 (7)	−0.0013 (8)
C6	0.0150 (10)	0.0226 (11)	0.0195 (10)	0.0024 (8)	0.0043 (8)	0.0015 (8)
C7	0.0224 (11)	0.0276 (12)	0.0201 (10)	0.0000 (9)	0.0110 (9)	−0.0006 (9)
C8	0.0234 (11)	0.0266 (11)	0.0173 (10)	−0.0043 (9)	0.0073 (9)	0.0025 (9)
C9	0.0213 (11)	0.0205 (11)	0.0243 (11)	0.0018 (9)	0.0052 (9)	0.0048 (9)
C10	0.0191 (10)	0.0199 (11)	0.0231 (10)	0.0010 (9)	0.0099 (9)	−0.0015 (9)
C11	0.0129 (9)	0.0166 (10)	0.0152 (9)	0.0010 (8)	0.0043 (8)	0.0025 (8)
C12	0.0244 (12)	0.0470 (15)	0.0183 (10)	0.0133 (11)	−0.0013 (9)	−0.0148 (10)
C13	0.0272 (13)	0.0526 (16)	0.0243 (12)	0.0208 (12)	0.0003 (10)	−0.0182 (11)
C14	0.0134 (9)	0.0151 (10)	0.0176 (9)	0.0004 (8)	0.0046 (8)	0.0013 (8)
C15	0.0191 (10)	0.0263 (11)	0.0151 (9)	0.0022 (9)	0.0045 (8)	−0.0036 (9)
C16	0.0185 (10)	0.0249 (11)	0.0194 (10)	0.0065 (9)	0.0070 (8)	−0.0034 (9)

Geometric parameters (Å, º) top

S1—O2	1.4283 (15)	C6—C7	1.382 (3)
S1—O1	1.4373 (15)	C6—H6	0.9500
S1—N3	1.6033 (18)	C7—C8	1.383 (3)
S1—C14	1.7754 (19)	C7—H7	0.9500
F1—C1	1.332 (3)	C8—C9	1.383 (3)
F2—C1	1.330 (2)	C8—H8	0.9500
F3—C1	1.332 (3)	C9—C10	1.389 (3)
N1—N2	1.359 (2)	C9—H9	0.9500
N1—C4	1.376 (3)	C10—H10	0.9500
N1—C11	1.436 (2)	C11—C12	1.374 (3)
N2—C2	1.333 (3)	C11—C16	1.378 (3)
N3—H1	0.84 (3)	C12—C13	1.387 (3)
N3—H2	0.87 (2)	C12—H12	0.9500
C1—C2	1.492 (3)	C13—C14	1.374 (3)
C2—C3	1.392 (3)	C13—H13	0.9500
C3—C4	1.379 (3)	C14—C15	1.377 (3)
C3—H3	0.9500	C15—C16	1.385 (3)
C4—C5	1.471 (3)	C15—H15	0.9500
C5—C6	1.397 (3)	C16—H16	0.9500
C5—C10	1.395 (3)

O2—S1—O1	119.85 (9)	C7—C6—H6	119.5
O2—S1—N3	108.36 (9)	C5—C6—H6	119.5
O1—S1—N3	106.20 (10)	C6—C7—C8	120.0 (2)
O2—S1—C14	106.32 (9)	C6—C7—H7	120.0
O1—S1—C14	107.22 (9)	C8—C7—H7	120.0
N3—S1—C14	108.50 (9)	C9—C8—C7	119.9 (2)
N2—N1—C4	112.43 (16)	C9—C8—H8	120.1
N2—N1—C11	117.95 (15)	C7—C8—H8	120.1
C4—N1—C11	129.36 (16)	C8—C9—C10	120.3 (2)
C2—N2—N1	103.70 (16)	C8—C9—H9	119.9
S1—N3—H1	113.6 (18)	C10—C9—H9	119.9
S1—N3—H2	112.6 (16)	C9—C10—C5	120.4 (2)
H1—N3—H2	115 (2)	C9—C10—H10	119.8
F2—C1—F1	106.47 (18)	C5—C10—H10	119.8
F2—C1—F3	107.48 (19)	C12—C11—C16	121.55 (19)
F1—C1—F3	106.57 (18)	C12—C11—N1	119.34 (17)
F2—C1—C2	110.94 (18)	C16—C11—N1	119.11 (18)
F1—C1—C2	112.57 (19)	C11—C12—C13	118.7 (2)
F3—C1—C2	112.45 (18)	C11—C12—H12	120.6
N2—C2—C3	112.93 (18)	C13—C12—H12	120.6
N2—C2—C1	119.24 (18)	C14—C13—C12	120.1 (2)
C3—C2—C1	127.82 (19)	C14—C13—H13	119.9
C4—C3—C2	105.10 (18)	C12—C13—H13	119.9
C4—C3—H3	127.5	C13—C14—C15	120.76 (19)
C2—C3—H3	127.5	C13—C14—S1	119.41 (16)
N1—C4—C3	105.85 (17)	C15—C14—S1	119.83 (15)
N1—C4—C5	125.03 (17)	C14—C15—C16	119.55 (19)
C3—C4—C5	129.12 (18)	C14—C15—H15	120.2
C6—C5—C10	118.42 (19)	C16—C15—H15	120.2
C6—C5—C4	118.74 (18)	C11—C16—C15	119.24 (19)
C10—C5—C4	122.85 (18)	C11—C16—H16	120.4
C7—C6—C5	121.0 (2)	C15—C16—H16	120.4

C4—N1—N2—C2	−0.4 (2)	C6—C7—C8—C9	1.1 (3)
C11—N1—N2—C2	174.33 (17)	C7—C8—C9—C10	−0.3 (3)
N1—N2—C2—C3	0.2 (2)	C8—C9—C10—C5	−1.7 (3)
N1—N2—C2—C1	179.01 (18)	C6—C5—C10—C9	2.7 (3)
F2—C1—C2—N2	156.75 (19)	C4—C5—C10—C9	−177.26 (19)
F1—C1—C2—N2	−84.1 (2)	N2—N1—C11—C12	60.5 (3)
F3—C1—C2—N2	36.3 (3)	C4—N1—C11—C12	−125.9 (2)
F2—C1—C2—C3	−24.6 (3)	N2—N1—C11—C16	−120.6 (2)
F1—C1—C2—C3	94.6 (3)	C4—N1—C11—C16	53.0 (3)
F3—C1—C2—C3	−145.0 (2)	C16—C11—C12—C13	−0.8 (4)
N2—C2—C3—C4	0.1 (2)	N1—C11—C12—C13	178.1 (2)
C1—C2—C3—C4	−178.6 (2)	C11—C12—C13—C14	−1.0 (4)
N2—N1—C4—C3	0.4 (2)	C12—C13—C14—C15	1.8 (4)
C11—N1—C4—C3	−173.52 (19)	C12—C13—C14—S1	−177.8 (2)
N2—N1—C4—C5	179.93 (17)	O2—S1—C14—C13	158.1 (2)
C11—N1—C4—C5	6.0 (3)	O1—S1—C14—C13	28.8 (2)
C2—C3—C4—N1	−0.3 (2)	N3—S1—C14—C13	−85.5 (2)
C2—C3—C4—C5	−179.8 (2)	O2—S1—C14—C15	−21.5 (2)
N1—C4—C5—C6	−149.8 (2)	O1—S1—C14—C15	−150.81 (17)
C3—C4—C5—C6	29.6 (3)	N3—S1—C14—C15	94.88 (19)
N1—C4—C5—C10	30.2 (3)	C13—C14—C15—C16	−0.7 (3)
C3—C4—C5—C10	−150.4 (2)	S1—C14—C15—C16	178.87 (16)
C10—C5—C6—C7	−1.8 (3)	C12—C11—C16—C15	1.9 (3)
C4—C5—C6—C7	178.14 (19)	N1—C11—C16—C15	−176.98 (18)
C5—C6—C7—C8	−0.1 (3)	C14—C15—C16—C11	−1.1 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H1···O1ⁱ	0.84 (3)	2.14 (3)	2.911 (2)	153 (2)
N3—H2···N2ⁱⁱ	0.87 (2)	2.21 (3)	3.049 (3)	164 (2)
C9—H9···O2ⁱⁱⁱ	0.95	2.49	3.376 (3)	155
C16—H16···O2^iv	0.95	2.55	3.137 (2)	120

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

Experimental details

Crystal data
Chemical formula	C₁₆H₁₂F₃N₃O₂S
M_r	367.35
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	16.2430 (7), 4.9461 (2), 21.2383 (8)
β (°)	111.231 (5)
V (Å³)	1590.47 (11)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.25
Crystal size (mm)	0.40 × 0.10 × 0.05

Data collection
Diffractometer	Agilent SuperNova Dual diffractometer with an Atlas detector
Absorption correction	Multi-scan (CrysAlis PRO; Agilent, 2010)
T_min, T_max	0.735, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	7901, 3560, 2876
R_int	0.031
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.043, 0.113, 1.06
No. of reflections	3560
No. of parameters	234
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.34, −0.49

Computer programs: CrysAlis PRO (Agilent, 2010), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2006), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H1···O1ⁱ	0.84 (3)	2.14 (3)	2.911 (2)	153 (2)
N3—H2···N2ⁱⁱ	0.87 (2)	2.21 (3)	3.049 (3)	164 (2)
C9—H9···O2ⁱⁱⁱ	0.95	2.49	3.376 (3)	155
C16—H16···O2^iv	0.95	2.55	3.137 (2)	120

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

Footnotes

‡Additional correspondence author, e-mail: aasiri2@kau.edu.sa.

Acknowledgements

The authors thank King Abdulaziz University and the University of Malaya for supporting this study.

References

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