4-(5-Phenyl-3-trifluoro-meth-yl-1H-pyrazol-1--yl)benzene-sulfonamide.

Significant twists between the aromatic rings are evident in the structure of the title compound, C(16)H(12)F(3)N(3)O(2)S. 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 supra-molecular tubes along the b-axis direction. These are connected into layers via C-H⋯O inter-actions 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 = 367.35

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.113

S = 1.06

3560 reflections

234 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.34 e Å−3

Δρmin = −0.49 e Å−3

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 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811033435/hg5083sup1.cif

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

Supplementary material file. DOI: 10.1107/S1600536811033435/hg5083Isup3.cml

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

C16H12F3N3O2S	F(000) = 752
Mr = 367.35	Dx = 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

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	Rint = 0.031
Detector resolution: 10.4041 pixels mm-1	θmax = 27.5°, θmin = 2.7°
ω scans	h = −16→21
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	k = −6→4
Tmin = 0.735, Tmax = 1.000	l = −27→27
7901 measured reflections

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(Fo2) + (0.0453P)2 + 1.0489P] where P = (Fo2 + 2Fc2)/3
3560 reflections	(Δ/σ)max < 0.001
234 parameters	Δρmax = 0.34 e Å−3
0 restraints	Δρmin = −0.49 e Å−3

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.

	x	y	z	Uiso*/Ueq
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*

	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)

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)

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···O2iv	0.95	2.55	3.137 (2)	120

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⋯O2iv	0.95	2.55	3.137 (2)	120

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .