4-[5-(Furan-2-yl)-3-trifluoro-methyl-1H-pyrazol-1-yl]benzene-sulfonamide.

In the title compound, C(14)H(10)F(3)N(3)O(3)S, there are significant twists in the mol-ecule, as seen in the values of the dihedral angles between the pyrazole ring and each of the furan [31.1 (2)°] and benzene rings [55.58 (10)°]. The amino N atom occupies a position almost normal to the benzene ring [N-S-C(ar)-C(ar) (ar = aromatic) torsion angle = 83.70 (19)°]. One amino H atom forms a hydrogen bond to the tricoordinate pyrazole N atom and the other inter-acts with a sulfonamide O atom, forming a supra-molecular chain along [010]. The chains are consolidated into a supra-molecular layers via C-H⋯O inter-actions involving the second sulfonamide O atom; layers stack along [10-1]. The furan ring was found to be disordered over two diagonally opposite orientations of equal occupancy.

Related literature

For background to the biological applications of sulfonamides, see: Croitoru et al. (2004 ▶); Dogruer et al. (2010 ▶). For the biological efficacy of F and CF3 in medicinal chemistry, see: Fokin & Kolomiyets (1988 ▶); Bonacorso et al. (2006 ▶). For related structures, see: Asiri et al. (2011 ▶, 2012 ▶).

Experimental

Crystal data

C14H10F3N3O3S

M = 357.31

Monoclinic,

a = 16.0536 (13) Å

b = 4.8173 (4) Å

c = 20.6202 (15) Å

β = 110.728 (8)°

V = 1491.4 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.27 mm−1

T = 100 K

0.25 × 0.10 × 0.05 mm

Data collection

Agilent SuperNova Dual diffractometer with an Atlas detector

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011 ▶) T min = 0.935, T max = 0.987

6503 measured reflections

3431 independent reflections

2400 reflections with I > 2σ(I)

R int = 0.051

Refinement

R[F 2 > 2σ(F 2)] = 0.069

wR(F 2) = 0.189

S = 1.06

3431 reflections

210 parameters

33 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.57 e Å−3

Δρmin = −0.63 e Å−3

Data collection: CrysAlis PRO (Agilent, 2011 ▶); 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: X-SEED (Barbour, 2001 ▶) and DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812011920/hb6693sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812011920/hb6693Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812011920/hb6693Isup3.cml

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

C14H10F3N3O3S	F(000) = 728
Mr = 357.31	Dx = 1.591 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 1899 reflections
a = 16.0536 (13) Å	θ = 2.5–27.5°
b = 4.8173 (4) Å	µ = 0.27 mm−1
c = 20.6202 (15) Å	T = 100 K
β = 110.728 (8)°	Prism, colourless
V = 1491.4 (2) Å3	0.25 × 0.10 × 0.05 mm
Z = 4

Agilent SuperNova Dual diffractometer with an Atlas detector	3431 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	2400 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.051
Detector resolution: 10.4041 pixels mm-1	θmax = 27.6°, θmin = 2.7°
ω scan	h = −20→15
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	k = −6→6
Tmin = 0.935, Tmax = 0.987	l = −26→25
6503 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)] = 0.069	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.189	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ2(Fo2) + (0.0768P)2 + 1.5964P] where P = (Fo2 + 2Fc2)/3
3431 reflections	(Δ/σ)max = 0.001
210 parameters	Δρmax = 0.57 e Å−3
33 restraints	Δρmin = −0.63 e Å−3

	x	y	z	Uiso*/Ueq	Occ. (<1)
S1	0.55947 (6)	0.78623 (17)	0.68278 (5)	0.0271 (3)
F1	0.67465 (17)	−0.1684 (5)	0.34173 (13)	0.0506 (7)
F2	0.7248 (2)	0.1593 (5)	0.29748 (11)	0.0559 (7)
F3	0.81166 (17)	−0.1668 (6)	0.35146 (14)	0.0605 (8)
O1	0.8796 (3)	0.7601 (14)	0.6001 (3)	0.0229 (13)	0.50
C5	0.9023 (5)	0.5273 (19)	0.5738 (4)	0.0223 (8)	0.50
C6	0.9876 (5)	0.4658 (18)	0.6122 (5)	0.0330 (13)	0.50
H6	1.0207	0.3124	0.6052	0.040*	0.50
C7	1.0177 (3)	0.6606 (15)	0.6621 (3)	0.0298 (17)	0.50
H7	1.0757	0.6683	0.6965	0.036*	0.50
C8	0.9510 (4)	0.8425 (11)	0.6547 (3)	0.035 (2)	0.50
H8	0.9537	1.0006	0.6829	0.042*	0.50
O1'	0.9946 (4)	0.4216 (15)	0.5961 (3)	0.0330 (13)	0.50
C5'	0.9085 (4)	0.501 (2)	0.5745 (4)	0.0223 (8)	0.50
C6'	0.9012 (4)	0.7080 (18)	0.6164 (4)	0.0229 (13)	0.50
H6'	0.8480	0.8029	0.6130	0.028*	0.50
C7'	0.9829 (4)	0.7561 (13)	0.6638 (3)	0.035 (2)	0.50
H7'	0.9972	0.8908	0.6998	0.042*	0.50
C8'	1.0406 (3)	0.5791 (14)	0.6513 (3)	0.0298 (17)	0.50
H8'	1.1027	0.5675	0.6768	0.036*	0.50
O2	0.61854 (18)	0.7401 (7)	0.75194 (14)	0.0456 (8)
O3	0.5296 (2)	1.0621 (5)	0.65989 (17)	0.0512 (9)
N1	0.70506 (19)	0.2448 (6)	0.44062 (14)	0.0242 (6)
N2	0.75031 (18)	0.3840 (6)	0.50020 (14)	0.0233 (6)
N3	0.4716 (2)	0.6093 (6)	0.67061 (15)	0.0246 (6)
C1	0.7446 (2)	−0.0041 (8)	0.35257 (17)	0.0289 (8)
C2	0.7692 (2)	0.1556 (7)	0.41875 (17)	0.0263 (7)
C3	0.8543 (2)	0.2312 (7)	0.46230 (17)	0.0254 (7)
H3	0.9094	0.1894	0.4571	0.030*
C4	0.8404 (2)	0.3810 (7)	0.51480 (17)	0.0240 (7)
C9	0.70348 (15)	0.4776 (5)	0.54273 (10)	0.0215 (7)
C10	0.72944 (14)	0.3863 (5)	0.61097 (11)	0.0441 (11)
H10	0.7778	0.2604	0.6285	0.053*
C11	0.68462 (16)	0.4790 (6)	0.65348 (8)	0.0384 (10)
H11	0.7024	0.4165	0.7001	0.046*
C12	0.61384 (15)	0.6630 (5)	0.62776 (10)	0.0238 (7)
C13	0.58788 (17)	0.7544 (5)	0.55953 (12)	0.0555 (14)
H13	0.5395	0.8802	0.5419	0.067*
C14	0.63270 (18)	0.6617 (5)	0.51701 (9)	0.0457 (11)
H14	0.6150	0.7242	0.4704	0.055*
H1	0.481 (2)	0.430 (3)	0.6746 (19)	0.032 (10)*
H2	0.4245 (17)	0.659 (8)	0.6352 (14)	0.041 (12)*

	U11	U22	U33	U12	U13	U23
S1	0.0345 (5)	0.0213 (4)	0.0295 (5)	−0.0030 (4)	0.0161 (4)	−0.0064 (3)
F1	0.0543 (16)	0.0558 (15)	0.0475 (15)	−0.0290 (13)	0.0251 (13)	−0.0239 (12)
F2	0.094 (2)	0.0472 (14)	0.0228 (12)	−0.0098 (14)	0.0162 (13)	−0.0029 (11)
F3	0.0408 (15)	0.0808 (19)	0.0521 (16)	0.0169 (13)	0.0069 (12)	−0.0314 (14)
O1	0.012 (3)	0.026 (3)	0.025 (3)	0.009 (2)	−0.001 (2)	−0.002 (3)
C5	0.0209 (18)	0.024 (2)	0.0233 (16)	0.0009 (15)	0.0097 (14)	0.0001 (15)
C6	0.0217 (18)	0.035 (3)	0.042 (3)	0.0019 (17)	0.012 (2)	−0.011 (2)
C7	0.011 (3)	0.042 (5)	0.032 (3)	−0.003 (3)	0.002 (2)	0.001 (3)
C8	0.048 (5)	0.032 (4)	0.030 (3)	−0.008 (4)	0.020 (3)	−0.008 (3)
O1'	0.0217 (18)	0.035 (3)	0.042 (3)	0.0019 (17)	0.012 (2)	−0.011 (2)
C5'	0.0209 (18)	0.024 (2)	0.0233 (16)	0.0009 (15)	0.0097 (14)	0.0001 (15)
C6'	0.012 (3)	0.026 (3)	0.025 (3)	0.009 (2)	−0.001 (2)	−0.002 (3)
C7'	0.048 (5)	0.032 (4)	0.030 (3)	−0.008 (4)	0.020 (3)	−0.008 (3)
C8'	0.011 (3)	0.042 (5)	0.032 (3)	−0.003 (3)	0.002 (2)	0.001 (3)
O2	0.0350 (15)	0.077 (2)	0.0248 (14)	−0.0097 (14)	0.0100 (12)	−0.0201 (14)
O3	0.082 (2)	0.0163 (13)	0.079 (2)	0.0030 (13)	0.058 (2)	−0.0024 (13)
N1	0.0237 (14)	0.0303 (15)	0.0172 (14)	−0.0032 (12)	0.0054 (11)	−0.0016 (11)
N2	0.0215 (14)	0.0286 (14)	0.0202 (14)	−0.0026 (12)	0.0079 (12)	−0.0006 (11)
N3	0.0285 (16)	0.0206 (14)	0.0247 (16)	0.0029 (12)	0.0094 (13)	0.0014 (12)
C1	0.0273 (18)	0.0350 (19)	0.0242 (17)	−0.0031 (15)	0.0089 (15)	−0.0037 (15)
C2	0.0258 (18)	0.0289 (17)	0.0242 (18)	−0.0009 (14)	0.0090 (15)	−0.0004 (14)
C3	0.0226 (17)	0.0306 (18)	0.0243 (17)	−0.0025 (14)	0.0100 (14)	−0.0011 (14)
C4	0.0199 (17)	0.0304 (17)	0.0224 (17)	−0.0006 (13)	0.0084 (14)	0.0028 (14)
C9	0.0215 (16)	0.0230 (16)	0.0200 (16)	−0.0025 (13)	0.0073 (13)	0.0004 (13)
C10	0.033 (2)	0.078 (3)	0.0251 (19)	0.031 (2)	0.0155 (17)	0.020 (2)
C11	0.027 (2)	0.066 (3)	0.0211 (18)	0.0152 (19)	0.0077 (15)	0.0105 (18)
C12	0.0291 (18)	0.0192 (15)	0.0249 (18)	−0.0011 (13)	0.0118 (15)	−0.0011 (13)
C13	0.082 (4)	0.057 (3)	0.036 (2)	0.054 (3)	0.032 (2)	0.024 (2)
C14	0.071 (3)	0.046 (2)	0.028 (2)	0.033 (2)	0.026 (2)	0.0176 (18)

S1—O2	1.423 (3)	C7'—H7'	0.9500
S1—O3	1.435 (3)	C8'—H8'	0.9500
S1—N3	1.590 (3)	N1—C2	1.334 (4)
S1—C12	1.7614 (17)	N1—N2	1.362 (4)
F1—C1	1.327 (4)	N2—C4	1.369 (4)
F2—C1	1.325 (4)	N2—C9	1.416 (3)
F3—C1	1.338 (4)	N3—H1	0.878 (10)
O1—C5	1.3500	N3—H2	0.878 (10)
O1—C8	1.3500	C1—C2	1.493 (5)
C5—C6	1.3500	C2—C3	1.391 (5)
C5—C4	1.452 (5)	C3—C4	1.383 (5)
C6—C7	1.3500	C3—H3	0.9500
C6—H6	0.9500	C9—C10	1.3900
C7—C8	1.3500	C9—C14	1.3900
C7—H7	0.9500	C10—C11	1.3900
C8—H8	0.9500	C10—H10	0.9500
O1'—C5'	1.3500	C11—C12	1.3900
O1'—C8'	1.3500	C11—H11	0.9500
C5'—C6'	1.3500	C12—C13	1.3900
C5'—C4	1.446 (5)	C13—C14	1.3900
C6'—C7'	1.3500	C13—H13	0.9500
C6'—H6'	0.9500	C14—H14	0.9500
C7'—C8'	1.3500
O2—S1—O3	120.06 (19)	S1—N3—H2	116 (3)
O2—S1—N3	108.29 (17)	H1—N3—H2	115 (4)
O3—S1—N3	105.67 (18)	F2—C1—F1	106.1 (3)
O2—S1—C12	106.65 (14)	F2—C1—F3	106.5 (3)
O3—S1—C12	106.52 (14)	F1—C1—F3	106.6 (3)
N3—S1—C12	109.37 (14)	F2—C1—C2	112.5 (3)
C5—O1—C8	108.0	F1—C1—C2	113.3 (3)
C6—C5—O1	108.0	F3—C1—C2	111.3 (3)
C6—C5—C4	129.5 (5)	N1—C2—C3	113.4 (3)
O1—C5—C4	122.5 (5)	N1—C2—C1	119.3 (3)
C5—C6—C7	108.0	C3—C2—C1	127.4 (3)
C5—C6—H6	126.0	C4—C3—C2	104.4 (3)
C7—C6—H6	126.0	C4—C3—H3	127.8
C8—C7—C6	108.0	C2—C3—H3	127.8
C8—C7—H7	126.0	N2—C4—C3	106.5 (3)
C6—C7—H7	126.0	N2—C4—C5'	127.1 (4)
C7—C8—O1	108.0	C3—C4—C5'	126.3 (4)
C7—C8—H8	126.0	N2—C4—C5	122.4 (4)
O1—C8—H8	126.0	C3—C4—C5	131.1 (5)
C5'—O1'—C8'	108.0	C10—C9—C14	120.0
O1'—C5'—C6'	108.0	C10—C9—N2	119.44 (17)
O1'—C5'—C4	122.9 (5)	C14—C9—N2	120.56 (17)
C6'—C5'—C4	129.0 (5)	C9—C10—C11	120.0
C7'—C6'—C5'	108.0	C9—C10—H10	120.0
C7'—C6'—H6'	126.0	C11—C10—H10	120.0
C5'—C6'—H6'	126.0	C12—C11—C10	120.0
C8'—C7'—C6'	108.0	C12—C11—H11	120.0
C8'—C7'—H7'	126.0	C10—C11—H11	120.0
C6'—C7'—H7'	126.0	C13—C12—C11	120.0
C7'—C8'—O1'	108.0	C13—C12—S1	120.39 (12)
C7'—C8'—H8'	126.0	C11—C12—S1	119.58 (12)
O1'—C8'—H8'	126.0	C12—C13—C14	120.0
C2—N1—N2	103.6 (3)	C12—C13—H13	120.0
N1—N2—C4	112.2 (3)	C14—C13—H13	120.0
N1—N2—C9	119.0 (3)	C13—C14—C9	120.0
C4—N2—C9	128.2 (3)	C13—C14—H14	120.0
S1—N3—H1	113 (3)	C9—C14—H14	120.0
C8—O1—C5—C6	0.0	C2—C3—C4—C5	−176.4 (7)
C8—O1—C5—C4	179.3 (12)	O1'—C5'—C4—N2	159.5 (5)
O1—C5—C6—C7	0.0	C6'—C5'—C4—N2	−22.8 (12)
C4—C5—C6—C7	−179.3 (13)	O1'—C5'—C4—C3	−18.1 (12)
C5—C6—C7—C8	0.0	C6'—C5'—C4—C3	159.7 (6)
C6—C7—C8—O1	0.0	O1'—C5'—C4—C5	−159 (10)
C5—O1—C8—C7	0.0	C6'—C5'—C4—C5	18 (9)
C8'—O1'—C5'—C6'	0.0	C6—C5—C4—N2	150.0 (6)
C8'—O1'—C5'—C4	178.2 (12)	O1—C5—C4—N2	−29.1 (12)
O1'—C5'—C6'—C7'	0.0	C6—C5—C4—C3	−33.5 (12)
C4—C5'—C6'—C7'	−178.0 (13)	O1—C5—C4—C3	147.3 (6)
C5'—C6'—C7'—C8'	0.0	C6—C5—C4—C5'	8 (9)
C6'—C7'—C8'—O1'	0.0	O1—C5—C4—C5'	−171 (10)
C5'—O1'—C8'—C7'	0.0	N1—N2—C9—C10	121.0 (3)
C2—N1—N2—C4	0.0 (3)	C4—N2—C9—C10	−49.5 (4)
C2—N1—N2—C9	−171.9 (3)	N1—N2—C9—C14	−59.7 (3)
N2—N1—C2—C3	0.3 (4)	C4—N2—C9—C14	129.8 (3)
N2—N1—C2—C1	−178.7 (3)	C14—C9—C10—C11	0.0
F2—C1—C2—N1	85.1 (4)	N2—C9—C10—C11	179.3 (2)
F1—C1—C2—N1	−35.3 (5)	C9—C10—C11—C12	0.0
F3—C1—C2—N1	−155.4 (3)	C10—C11—C12—C13	0.0
F2—C1—C2—C3	−93.8 (4)	C10—C11—C12—S1	−178.32 (19)
F1—C1—C2—C3	145.8 (4)	O2—S1—C12—C13	−159.41 (19)
F3—C1—C2—C3	25.7 (5)	O3—S1—C12—C13	−30.1 (2)
N1—C2—C3—C4	−0.5 (4)	N3—S1—C12—C13	83.70 (19)
C1—C2—C3—C4	178.4 (3)	O2—S1—C12—C11	18.9 (2)
N1—N2—C4—C3	−0.3 (4)	O3—S1—C12—C11	148.3 (2)
C9—N2—C4—C3	170.6 (3)	N3—S1—C12—C11	−98.0 (2)
N1—N2—C4—C5'	−178.3 (7)	C11—C12—C13—C14	0.0
C9—N2—C4—C5'	−7.3 (8)	S1—C12—C13—C14	178.31 (19)
N1—N2—C4—C5	176.9 (6)	C12—C13—C14—C9	0.0
C9—N2—C4—C5	−12.1 (8)	C10—C9—C14—C13	0.0
C2—C3—C4—N2	0.5 (4)	N2—C9—C14—C13	−179.3 (2)
C2—C3—C4—C5'	178.4 (7)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H1···O3i	0.88 (1)	2.00 (2)	2.830 (4)	158 (3)
N3—H2···N1ii	0.88 (1)	2.17 (1)	3.032 (4)	170 (4)
C8—H8···O2iii	0.95	2.36	3.185 (7)	145
C10—H10···O2iv	0.95	2.44	3.092 (4)	126

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H1⋯O3i	0.88 (1)	2.00 (2)	2.830 (4)	158 (3)
N3—H2⋯N1ii	0.88 (1)	2.17 (1)	3.032 (4)	170 (4)
C8—H8⋯O2iii	0.95	2.36	3.185 (7)	145
C10—H10⋯O2iv	0.95	2.44	3.092 (4)	126

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