4-[(1,3-Thia-zol-2-yl)sulfamo-yl]phenyl 2,2,2-trifluoro-acetate.

In the title compound, C(11)H(7)F(3)N(2)O(4)S(2), the 1,3-thia-zol-2-amine residue is almost perpendicular to the central benzene ring [dihedral angle = 84.3 (2)°]. There is a small twist between the benzene ring and the ester group [C-O-C-C torsion angle = 9.8 (6)°]. Thus, the mol-ecule has an L-shape. Inversion-related dimers are connected in the crystal packing by pairs of N-H⋯N hydrogen bonds formed between the amine H and thia-zole N atom via eight-membered {⋯HNCN}(2) synthons.

Related literature

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

Experimental

Crystal data

C11H7F3N2O4S2

M = 352.31

Monoclinic,

a = 8.7498 (5) Å

b = 14.4343 (9) Å

c = 10.7225 (5) Å

β = 96.749 (5)°

V = 1344.84 (13) Å3

Z = 4

Mo Kα radiation

μ = 0.45 mm−1

T = 100 K

0.30 × 0.30 × 0.10 mm

Data collection

Agilent SuperNova Dual diffractometer with an Atlas detector

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011 ▶) T min = 0.876, T max = 0.956

12068 measured reflections

3105 independent reflections

2252 reflections with I > 2σ(I)

R int = 0.036

Refinement

R[F 2 > 2σ(F 2)] = 0.071

wR(F 2) = 0.215

S = 1.06

3105 reflections

199 parameters

H-atom parameters constrained

Δρmax = 0.69 e Å−3

Δρmin = −0.41 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/S1600536812011683/hg5192sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812011683/hg5192Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812011683/hg5192Isup3.cml

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

C11H7F3N2O4S2	F(000) = 712
Mr = 352.31	Dx = 1.740 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 3265 reflections
a = 8.7498 (5) Å	θ = 2.3–27.5°
b = 14.4343 (9) Å	µ = 0.45 mm−1
c = 10.7225 (5) Å	T = 100 K
β = 96.749 (5)°	Irregular, light-yellow
V = 1344.84 (13) Å3	0.30 × 0.30 × 0.10 mm
Z = 4

Agilent SuperNova Dual diffractometer with an Atlas detector	3105 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	2252 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.036
Detector resolution: 10.4041 pixels mm-1	θmax = 27.6°, θmin = 2.4°
ω scan	h = −11→11
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	k = −13→18
Tmin = 0.876, Tmax = 0.956	l = −13→13
12068 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)] = 0.071	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.215	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.1054P)2 + 2.1576P] where P = (Fo2 + 2Fc2)/3
3105 reflections	(Δ/σ)max = 0.001
199 parameters	Δρmax = 0.69 e Å−3
0 restraints	Δρmin = −0.41 e Å−3

	x	y	z	Uiso*/Ueq
S1	0.83675 (13)	0.46698 (8)	0.30886 (10)	0.0500 (3)
S2	0.55748 (13)	0.61673 (8)	0.24923 (9)	0.0454 (3)
F1	1.4449 (3)	0.9101 (2)	0.4037 (3)	0.0707 (8)
F2	1.2781 (3)	1.0011 (2)	0.4699 (3)	0.0679 (8)
F3	1.3609 (4)	1.0282 (2)	0.2933 (3)	0.0684 (8)
O1	0.4182 (4)	0.6682 (2)	0.2516 (3)	0.0549 (8)
O2	0.5788 (4)	0.5696 (2)	0.1331 (2)	0.0547 (8)
O3	1.0875 (4)	0.8720 (2)	0.3708 (3)	0.0540 (8)
O4	1.2090 (4)	0.8779 (3)	0.1895 (3)	0.0621 (9)
N1	0.6932 (4)	0.4364 (2)	0.4965 (3)	0.0429 (8)
N2	0.5655 (4)	0.5461 (2)	0.3653 (3)	0.0407 (8)
H2	0.4899	0.5458	0.4127	0.049*
C1	0.9139 (5)	0.3890 (3)	0.4238 (4)	0.0525 (11)
H1	1.0078	0.3563	0.4215	0.063*
C2	0.8241 (5)	0.3813 (3)	0.5146 (4)	0.0487 (10)
H2A	0.8471	0.3419	0.5853	0.058*
C3	0.6816 (5)	0.4886 (3)	0.3920 (3)	0.0393 (9)
C4	0.7160 (5)	0.6916 (3)	0.2825 (3)	0.0390 (9)
C5	0.8250 (5)	0.7001 (3)	0.1993 (3)	0.0444 (10)
H5	0.8150	0.6645	0.1242	0.053*
C6	0.9482 (5)	0.7601 (3)	0.2248 (3)	0.0422 (9)
H6	1.0222	0.7663	0.1672	0.051*
C7	0.9628 (4)	0.8114 (3)	0.3362 (3)	0.0356 (8)
C8	0.8530 (5)	0.8018 (3)	0.4203 (3)	0.0408 (9)
H8	0.8636	0.8362	0.4963	0.049*
C9	0.7304 (5)	0.7431 (3)	0.3940 (3)	0.0414 (9)
H9	0.6556	0.7374	0.4510	0.050*
C10	1.1941 (5)	0.8985 (3)	0.2972 (4)	0.0484 (10)
C11	1.3199 (6)	0.9613 (4)	0.3672 (5)	0.0544 (11)

	U11	U22	U33	U12	U13	U23
S1	0.0531 (7)	0.0573 (7)	0.0405 (6)	−0.0071 (5)	0.0083 (5)	−0.0031 (5)
S2	0.0539 (6)	0.0557 (6)	0.0244 (5)	−0.0088 (5)	−0.0045 (4)	0.0085 (4)
F1	0.0512 (16)	0.0725 (19)	0.086 (2)	0.0087 (14)	−0.0015 (14)	0.0160 (17)
F2	0.0624 (17)	0.081 (2)	0.0607 (17)	−0.0100 (15)	0.0071 (13)	−0.0193 (15)
F3	0.0685 (19)	0.0635 (18)	0.0730 (19)	−0.0053 (14)	0.0073 (15)	0.0189 (15)
O1	0.0508 (17)	0.073 (2)	0.0385 (15)	−0.0029 (15)	−0.0064 (13)	0.0167 (15)
O2	0.076 (2)	0.0631 (19)	0.0219 (13)	−0.0207 (17)	−0.0062 (13)	0.0018 (13)
O3	0.062 (2)	0.0564 (19)	0.0436 (16)	0.0032 (15)	0.0051 (14)	0.0015 (14)
O4	0.071 (2)	0.073 (2)	0.0442 (18)	−0.0039 (18)	0.0159 (15)	−0.0029 (16)
N1	0.059 (2)	0.0393 (18)	0.0288 (15)	0.0003 (16)	−0.0016 (14)	−0.0013 (13)
N2	0.0466 (18)	0.051 (2)	0.0247 (14)	−0.0051 (15)	0.0032 (13)	0.0077 (13)
C1	0.054 (3)	0.049 (2)	0.053 (3)	0.003 (2)	−0.002 (2)	−0.013 (2)
C2	0.063 (3)	0.042 (2)	0.038 (2)	0.003 (2)	−0.0043 (19)	−0.0034 (17)
C3	0.051 (2)	0.041 (2)	0.0248 (17)	−0.0051 (18)	−0.0011 (15)	−0.0027 (15)
C4	0.050 (2)	0.042 (2)	0.0229 (16)	−0.0013 (17)	−0.0038 (15)	0.0024 (15)
C5	0.063 (3)	0.048 (2)	0.0211 (16)	−0.004 (2)	0.0020 (16)	−0.0050 (15)
C6	0.054 (2)	0.047 (2)	0.0266 (17)	0.0037 (19)	0.0092 (16)	−0.0010 (16)
C7	0.046 (2)	0.0314 (18)	0.0282 (17)	0.0078 (16)	−0.0004 (15)	0.0033 (14)
C8	0.057 (2)	0.041 (2)	0.0239 (16)	0.0028 (18)	0.0035 (16)	−0.0042 (15)
C9	0.053 (2)	0.049 (2)	0.0231 (16)	−0.0024 (18)	0.0067 (15)	0.0023 (16)
C10	0.051 (2)	0.050 (2)	0.044 (2)	0.0062 (19)	0.0088 (19)	0.0039 (19)
C11	0.050 (3)	0.062 (3)	0.051 (3)	0.007 (2)	0.006 (2)	0.007 (2)

S1—C3	1.738 (4)	N2—H2	0.8800
S1—C1	1.745 (5)	C1—C2	1.326 (6)
S2—O1	1.430 (4)	C1—H1	0.9500
S2—O2	1.450 (3)	C2—H2A	0.9500
S2—N2	1.604 (3)	C4—C5	1.386 (6)
S2—C4	1.762 (4)	C4—C9	1.400 (5)
F1—C11	1.339 (5)	C5—C6	1.385 (6)
F2—C11	1.331 (5)	C5—H5	0.9500
F3—C11	1.325 (5)	C6—C7	1.398 (5)
O3—C10	1.346 (5)	C6—H6	0.9500
O3—C7	1.414 (5)	C7—C8	1.399 (5)
O4—C10	1.214 (5)	C8—C9	1.370 (6)
N1—C3	1.344 (5)	C8—H8	0.9500
N1—C2	1.389 (6)	C9—H9	0.9500
N2—C3	1.317 (5)	C10—C11	1.550 (7)
C3—S1—C1	90.8 (2)	C6—C5—C4	120.4 (3)
O1—S2—O2	117.08 (19)	C6—C5—H5	119.8
O1—S2—N2	106.00 (19)	C4—C5—H5	119.8
O2—S2—N2	111.73 (19)	C5—C6—C7	119.4 (4)
O1—S2—C4	109.3 (2)	C5—C6—H6	120.3
O2—S2—C4	106.50 (19)	C7—C6—H6	120.3
N2—S2—C4	105.72 (17)	C6—C7—C8	119.8 (4)
C10—O3—C7	126.0 (3)	C6—C7—O3	122.8 (3)
C3—N1—C2	114.7 (4)	C8—C7—O3	117.3 (3)
C3—N2—S2	122.1 (3)	C9—C8—C7	120.6 (3)
C3—N2—H2	119.0	C9—C8—H8	119.7
S2—N2—H2	119.0	C7—C8—H8	119.7
C2—C1—S1	111.0 (4)	C8—C9—C4	119.5 (4)
C2—C1—H1	124.5	C8—C9—H9	120.2
S1—C1—H1	124.5	C4—C9—H9	120.2
C1—C2—N1	113.6 (4)	O4—C10—O3	130.4 (5)
C1—C2—H2A	123.2	O4—C10—C11	117.0 (4)
N1—C2—H2A	123.2	O3—C10—C11	112.6 (4)
N2—C3—N1	121.0 (4)	F3—C11—F2	107.4 (4)
N2—C3—S1	129.1 (3)	F3—C11—F1	107.9 (4)
N1—C3—S1	109.9 (3)	F2—C11—F1	106.9 (4)
C5—C4—C9	120.2 (4)	F3—C11—C10	111.3 (4)
C5—C4—S2	120.6 (3)	F2—C11—C10	113.9 (4)
C9—C4—S2	119.2 (3)	F1—C11—C10	109.2 (4)
O1—S2—N2—C3	−178.9 (3)	S2—C4—C5—C6	179.0 (3)
O2—S2—N2—C3	52.5 (4)	C4—C5—C6—C7	0.7 (6)
C4—S2—N2—C3	−63.0 (4)	C5—C6—C7—C8	−0.1 (6)
C3—S1—C1—C2	0.9 (4)	C5—C6—C7—O3	178.1 (3)
S1—C1—C2—N1	−0.1 (5)	C10—O3—C7—C6	9.8 (6)
C3—N1—C2—C1	−1.1 (5)	C10—O3—C7—C8	−171.9 (4)
S2—N2—C3—N1	173.6 (3)	C6—C7—C8—C9	−0.6 (6)
S2—N2—C3—S1	−6.0 (5)	O3—C7—C8—C9	−178.9 (3)
C2—N1—C3—N2	−178.0 (4)	C7—C8—C9—C4	0.7 (6)
C2—N1—C3—S1	1.7 (4)	C5—C4—C9—C8	−0.1 (6)
C1—S1—C3—N2	178.2 (4)	S2—C4—C9—C8	−179.7 (3)
C1—S1—C3—N1	−1.5 (3)	C7—O3—C10—O4	−0.2 (8)
O1—S2—C4—C5	−123.6 (3)	C7—O3—C10—C11	−176.8 (3)
O2—S2—C4—C5	3.7 (4)	O4—C10—C11—F3	41.5 (6)
N2—S2—C4—C5	122.7 (3)	O3—C10—C11—F3	−141.4 (4)
O1—S2—C4—C9	56.0 (4)	O4—C10—C11—F2	163.1 (4)
O2—S2—C4—C9	−176.7 (3)	O3—C10—C11—F2	−19.8 (5)
N2—S2—C4—C9	−57.7 (4)	O4—C10—C11—F1	−77.6 (5)
C9—C4—C5—C6	−0.6 (6)	O3—C10—C11—F1	99.5 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···N1i	0.88	1.99	2.858 (5)	171

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯N1i	0.88	1.99	2.858 (5)	171

Symmetry code: (i) .