N-(4-Chloro­phen­yl)-1,1,1-trifluoro-N-(trifluoro­methyl­sulfon­yl)methane­sulfonamide

Boechat, N.; Santos Lages, A. dos; Kover, W.B.; Tiekink, E.R.T.; Wardell, J.L.; Wardell, S.M.S.V.

doi:10.1107/S1600536810003326

organic compounds

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ISSN: 2056-9890

Volume 66| Part 3| March 2010| Pages o506-o507

doi:10.1107/S1600536810003326

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N-(4-Chlorophenyl)-1,1,1-trifluoro-N-(trifluoromethylsulfonyl)methanesulfonamide

Núbia Boechat,^a Adriana dos Santos Lages,^a Warner B. Kover,^b Edward R. T. Tiekink,^c ^* James L. Wardell ^d ‡ and Solange M. S. V. Wardell ^e

^aFundação Oswaldo Cruz, Instituto de Tecnologia em Fármacos, Departamento de Síntese Orgânica, Manguinhos, CEP 21041250 Rio de Janeiro, RJ, Brazil, ^bUniversidade Federal do Rio de Janeiro, Departamento de Química Orgânica, Instituto de Quıímica, Cidade Universitária, 21949-900 Rio de Janeiro, RJ, Brazil, ^cDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia, ^dCentro de Desenvolvimento Tecnológico em Saúde (CDTS), Fundação Oswaldo Cruz (FIOCRUZ), Casa Amarela, Campus de Manguinhos, Av. Brasil 4365, 21040-900 Rio de Janeiro, RJ, Brazil, and ^eCHEMSOL, 1 Harcourt Road, Aberdeen AB15 5NY, Scotland
^*Correspondence e-mail: edward.tiekink@gmail.com

(Received 26 January 2010; accepted 27 January 2010; online 3 February 2010)

The title molecule, also called 4-chloro-N,N-bis(trifluoromethanesulfonyl)aniline, C₈H₄ClF₆NO₄S₂, has non-crystallographic twofold symmetry with the pseudo-axis aligned along the Cl—C⋯C—N backbone of the molecule: the SO₂CF₃ residues lie to either side of the benzene ring. In the crystal, the presence of C—H⋯O contacts lead to the formation of a sequence of 12-membered {⋯HC₂NSO}₂ synthons within a supramolecular chain aligned along [101].

Related literature

For uses of N,N-bis(trifluoromethanesulfonyl)aniline derivatives, see: Zeller (2001 ); Wulff et al. (1986 ). For general background to the synthesis, see: Deprez et al. (1995 ); Greenfield & Crosanu (2008 ). For a previous synthesis of the title compound, see: Laali et al. (2007 ).

Experimental

Crystal data

C₈H₄ClF₆NO₄S₂
M_r = 391.70
Monoclinic, P 2₁ /c
a = 11.5998 (3) Å
b = 13.4423 (4) Å
c = 9.0548 (2) Å
β = 108.014 (2)°
V = 1342.69 (6) Å³
Z = 4
Mo Kα radiation
μ = 0.68 mm⁻¹
T = 120 K
0.40 × 0.25 × 0.25 mm

Data collection

Nonius KappaCCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2007 ) T_min = 0.821, T_max = 1.000
17100 measured reflections
3047 independent reflections
2806 reflections with I > 2σ(I)
R_int = 0.023

Refinement

R[F² > 2σ(F²)] = 0.031
wR(F²) = 0.082
S = 1.04
3047 reflections
199 parameters
H-atom parameters constrained
Δρ_max = 0.62 e Å⁻³
Δρ_min = −0.41 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯O3ⁱ	0.95	2.57	3.496 (2)	164
C5—H5⋯O1ⁱⁱ	0.95	2.59	3.385 (2)	141
Symmetry codes: (i) -x+1, -y+2, -z+1; (ii) -x+2, -y+2, -z+2.

Data collection: COLLECT (Hooft, 1998 ); cell refinement: DENZO (Otwinowski & Minor, 1997 ) and COLLECT; data reduction: DENZO and COLLECT; 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/S1600536810003326/hb5319sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810003326/hb5319Isup2.hkl

checkCIF report

Comment top

N,N-Bis(trifluoromethanesulfonyl)aniline derivatives find use in synthetic chemistry such as mild triflating reagents (Zeller, 2001; Wulff et al., 1986). Following a literature procedure to p-ClC₆H₄NHSO₂CF₃, using p-ClC₆H₄NH₂, (F₃CSO₂)O and Et₃N in CH₂Cl₂ at 213 K, a little of the di-substituted compound, p-ClC₆H₄(NSO₂CF₃), (I), was isolated as a side-product (Greenfield & Crosanu, 2008; Deprez et al., 1995). Compound (I) has been reported previously (Laali et al., 2007) and the X-ray structure determination is reported herein.

In (I), the SO₂CF₃ groups occupy approximately orthogonal positions to either side of the aromatic ring: the C3/C4/N1/S1, S2 torsion angles are 77.44 (17) and -101.55 (15) °, respectively; the dihedral angle formed between the benzene ring and NS₂ group is 78.13 (6) °. The CF₃ groups lie to either side of the molecule and fold back over the benzene ring so that, overall, the molecule has non-crystallographic 2-fold symmetry when viewed down the Cl1–C1–C4–N1 axis.

Supramolecular aggregation in (I) is dominated by C–H···O interactions that lead to the formation of a sequence of 12-membered {···HC₂NSO}₂ synthons aligned along [1 0 1], Fig. 2 and Table 1. Chains are connected into layers through the agency of C–Cl···π interactions between centrosymmetrically related residues [C1–Cl1···ring centroid(C1–C6)ⁱ = 3.4592 (8) Å with angle at Cl1 = 92.46 (6) ° for i: 2-x, 2-y, 1-z]. The layers thus formed stack along the b axis with the closest contacts between successive layers being of the type C–F···π [C8–F4···ring centroid(C1–C6)ⁱⁱ = 3.4708 (16) Å with angle at F4 = 122.83 (11) ° for ii: x, 3/2-y,1/2+z].

Related literature top

For uses of N,N-bis(trifluoromethanesulfonyl)aniline derivatives, see: Zeller (2001); Wulff et al. (1986). For general background to the synthesis, see: Deprez et al. (1995); Greenfield & Crosanu (2008). For a previous synthesis of the title compound, see: Laali et al. (2007).

Experimental top

To a cooled (213 K) solution of p-ClC₆H₄NH₂ (11.5 g, 9.0 mmol) and triethylamine (1.50 ml; 10.8 mmol, 1.20 eq.) in CH₂Cl₂ (40 ml) was slowly added a solution of trifluoromethanesulfonic anhydride (2.40 ml; 13.5 mmol, 1.50 eq) in CH₂Cl₂ (40 ml). After the mixture was stirred at 213-223 K for 1 h, water (30 ml) was added. The mixture was allowed to warm to room temperature, and the organic layer was decanted, washed with water, dried, and evaporated. The products, N-(4-chlorophenyl)trifluoromethylsulfonamide and N-(4-chlorophenyl)-bis-trifluoromethylsulfonamide, (I), were purified by chromatography on silica gel with hexane as eluent. Products were recrystallized from hexane. Characterisation data for (I): m.pt. 346-348 K, ¹H-NMR (500 MHz, CDCl₃) δ: 7.34 (2H), 7.50 (2H) p.p.m. ¹³C-NMR (125 MHz, CDCl₃) δ: 119.36 (q, ¹J(C,F) = 325 Hz), 125.17 (C3), 130.06, 132.18, 138.84 p.p.m. ¹⁹F-NMR (376 MHz, CDCl₃) δ: 71.11 p.p.m.

Computing details top

Data collection: COLLECT (Hooft, 1998); cell refinement: DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998); data reduction: DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998); 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 displacement ellipsoids at the 50% probability level.
	Fig. 2. A view of the supramolecular chain in (I) aligned along [1 0 1] and mediated by C–H···O interactions (blue dashed lines). Colour code: Cl, cyan; S, yellow; F, pink; O, red; N, blue; C, grey; and H, green.
	Fig. 3. View of the stacking of layers in (I). The C–H···O interactions are shown as blue dashed lines. Colour code: Cl, cyan; S, yellow; F, pink; O, red; N, blue; C, grey; and H, green.

N-(4-Chlorophenyl)-1,1,1-trifluoro-N- (trifluoromethylsulfonyl)methanesulfonamide top

Crystal data top

C₈H₄ClF₆NO₄S₂	F(000) = 776
M_r = 391.70	D_x = 1.938 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2983 reflections
a = 11.5998 (3) Å	θ = 2.9–27.5°
b = 13.4423 (4) Å	µ = 0.68 mm⁻¹
c = 9.0548 (2) Å	T = 120 K
β = 108.014 (2)°	Block, colourless
V = 1342.69 (6) Å³	0.40 × 0.25 × 0.25 mm
Z = 4

Data collection top

Nonius KappaCCD area-detector diffractometer	3047 independent reflections
Radiation source: Enraf Nonius FR591 rotating anode	2806 reflections with I > 2σ(I)
10 cm confocal mirrors monochromator	R_int = 0.023
Detector resolution: 9.091 pixels mm^-1	θ_max = 27.5°, θ_min = 2.9°
ϕ and ω scans	h = −15→15
Absorption correction: multi-scan (SADABS; Sheldrick, 2007)	k = −17→17
T_min = 0.821, T_max = 1.000	l = −11→11
17100 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)] = 0.031	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.082	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0407P)² + 1.1662P] where P = (F_o² + 2F_c²)/3
3047 reflections	(Δ/σ)_max = 0.001
199 parameters	Δρ_max = 0.62 e Å⁻³
0 restraints	Δρ_min = −0.41 e Å⁻³

Crystal data top

C₈H₄ClF₆NO₄S₂	V = 1342.69 (6) Å³
M_r = 391.70	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 11.5998 (3) Å	µ = 0.68 mm⁻¹
b = 13.4423 (4) Å	T = 120 K
c = 9.0548 (2) Å	0.40 × 0.25 × 0.25 mm
β = 108.014 (2)°

Data collection top

Nonius KappaCCD area-detector diffractometer	3047 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2007)	2806 reflections with I > 2σ(I)
T_min = 0.821, T_max = 1.000	R_int = 0.023
17100 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.031	0 restraints
wR(F²) = 0.082	H-atom parameters constrained
S = 1.04	Δρ_max = 0.62 e Å⁻³
3047 reflections	Δρ_min = −0.41 e Å⁻³
199 parameters

Special details top

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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
Cl1	0.97286 (4)	0.86092 (3)	0.34987 (5)	0.02733 (12)
S1	0.78053 (4)	1.09197 (3)	0.91222 (4)	0.01889 (11)
S2	0.59031 (4)	0.94255 (3)	0.78741 (5)	0.01943 (11)
F1	0.70006 (16)	1.20000 (9)	0.66292 (14)	0.0497 (4)
F2	0.75847 (13)	1.28200 (9)	0.87505 (16)	0.0449 (3)
F3	0.58975 (12)	1.20628 (11)	0.8139 (2)	0.0551 (4)
F4	0.69058 (14)	0.77016 (10)	0.86879 (18)	0.0525 (4)
F5	0.71980 (16)	0.87281 (11)	1.05802 (17)	0.0663 (5)
F6	0.54674 (13)	0.80495 (10)	0.96076 (16)	0.0478 (3)
O1	0.90194 (11)	1.10259 (10)	0.91208 (15)	0.0280 (3)
O2	0.74816 (13)	1.08338 (10)	1.04986 (15)	0.0293 (3)
O3	0.54372 (11)	0.89593 (10)	0.64061 (14)	0.0254 (3)
O4	0.52094 (12)	1.00882 (11)	0.84680 (16)	0.0308 (3)
N1	0.72049 (12)	0.99798 (10)	0.79108 (15)	0.0167 (3)
C1	0.89885 (15)	0.90047 (12)	0.4795 (2)	0.0192 (3)
C2	0.79853 (15)	0.96166 (12)	0.42518 (19)	0.0201 (3)
H2	0.7706	0.9812	0.3192	0.024*
C3	0.73954 (14)	0.99385 (12)	0.52852 (18)	0.0182 (3)
H3	0.6704	1.0358	0.4943	0.022*
C4	0.78292 (14)	0.96396 (12)	0.68241 (18)	0.0162 (3)
C5	0.88287 (15)	0.90243 (12)	0.73621 (19)	0.0198 (3)
H5	0.9106	0.8824	0.8420	0.024*
C6	0.94185 (15)	0.87055 (12)	0.6327 (2)	0.0218 (3)
H6	1.0110	0.8286	0.6668	0.026*
C7	0.70024 (18)	1.20199 (13)	0.8072 (2)	0.0258 (4)
C8	0.64203 (18)	0.84073 (14)	0.9298 (2)	0.0301 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0291 (2)	0.0285 (2)	0.0294 (2)	−0.00347 (16)	0.01644 (18)	−0.01089 (17)
S1	0.0231 (2)	0.0187 (2)	0.01481 (19)	−0.00119 (14)	0.00583 (15)	−0.00231 (13)
S2	0.0178 (2)	0.0220 (2)	0.0187 (2)	−0.00101 (14)	0.00585 (15)	0.00126 (14)
F1	0.0996 (12)	0.0286 (6)	0.0236 (6)	0.0191 (7)	0.0229 (7)	0.0060 (5)
F2	0.0691 (9)	0.0188 (5)	0.0461 (7)	−0.0062 (6)	0.0167 (7)	−0.0067 (5)
F3	0.0402 (7)	0.0402 (7)	0.0918 (12)	0.0177 (6)	0.0303 (8)	0.0267 (7)
F4	0.0650 (9)	0.0347 (7)	0.0620 (9)	0.0206 (7)	0.0257 (8)	0.0194 (6)
F5	0.0872 (11)	0.0427 (8)	0.0367 (7)	−0.0277 (8)	−0.0281 (7)	0.0189 (6)
F6	0.0593 (9)	0.0433 (7)	0.0469 (8)	−0.0179 (6)	0.0252 (7)	0.0100 (6)
O1	0.0216 (6)	0.0317 (7)	0.0290 (7)	−0.0046 (5)	0.0053 (5)	−0.0099 (5)
O2	0.0462 (8)	0.0276 (7)	0.0174 (6)	−0.0026 (6)	0.0146 (6)	−0.0025 (5)
O3	0.0211 (6)	0.0313 (7)	0.0216 (6)	−0.0065 (5)	0.0032 (5)	−0.0025 (5)
O4	0.0267 (7)	0.0358 (7)	0.0357 (7)	0.0025 (6)	0.0182 (6)	−0.0020 (6)
N1	0.0178 (6)	0.0171 (6)	0.0158 (6)	−0.0006 (5)	0.0060 (5)	−0.0025 (5)
C1	0.0216 (8)	0.0159 (7)	0.0226 (8)	−0.0044 (6)	0.0105 (6)	−0.0059 (6)
C2	0.0241 (8)	0.0204 (8)	0.0152 (7)	−0.0020 (6)	0.0055 (6)	−0.0020 (6)
C3	0.0182 (7)	0.0175 (7)	0.0171 (7)	0.0018 (6)	0.0027 (6)	0.0002 (6)
C4	0.0163 (7)	0.0166 (7)	0.0160 (7)	−0.0004 (6)	0.0055 (6)	−0.0015 (6)
C5	0.0197 (8)	0.0207 (8)	0.0176 (8)	0.0021 (6)	0.0038 (6)	0.0024 (6)
C6	0.0190 (8)	0.0193 (8)	0.0269 (8)	0.0029 (6)	0.0069 (7)	−0.0003 (6)
C7	0.0371 (10)	0.0185 (8)	0.0244 (9)	0.0017 (7)	0.0134 (7)	0.0002 (6)
C8	0.0360 (10)	0.0247 (9)	0.0258 (9)	−0.0082 (7)	0.0040 (8)	0.0053 (7)

Geometric parameters (Å, º) top

Cl1—C1	1.7380 (16)	F5—C8	1.304 (2)
S1—O2	1.4131 (13)	F6—C8	1.313 (2)
S1—O1	1.4160 (13)	N1—C4	1.4637 (19)
S1—N1	1.6769 (13)	C1—C6	1.381 (2)
S1—C7	1.8470 (18)	C1—C2	1.385 (2)
S2—O4	1.4135 (13)	C2—C3	1.388 (2)
S2—O3	1.4168 (13)	C2—H2	0.9500
S2—N1	1.6749 (14)	C3—C4	1.387 (2)
S2—C8	1.8483 (19)	C3—H3	0.9500
F1—C7	1.306 (2)	C4—C5	1.384 (2)
F2—C7	1.317 (2)	C5—C6	1.388 (2)
F3—C7	1.303 (2)	C5—H5	0.9500
F4—C8	1.309 (3)	C6—H6	0.9500

O2—S1—O1	123.00 (9)	C2—C3—H3	120.5
O2—S1—N1	110.21 (8)	C5—C4—C3	122.06 (15)
O1—S1—N1	106.70 (7)	C5—C4—N1	119.00 (14)
O2—S1—C7	106.88 (8)	C3—C4—N1	118.94 (14)
O1—S1—C7	105.19 (9)	C4—C5—C6	118.75 (15)
N1—S1—C7	103.02 (8)	C4—C5—H5	120.6
O4—S2—O3	122.60 (8)	C6—C5—H5	120.6
O4—S2—N1	109.14 (8)	C1—C6—C5	119.21 (15)
O3—S2—N1	107.18 (7)	C1—C6—H6	120.4
O4—S2—C8	107.55 (9)	C5—C6—H6	120.4
O3—S2—C8	105.91 (8)	F3—C7—F1	110.51 (18)
N1—S2—C8	102.67 (8)	F3—C7—F2	108.18 (16)
C4—N1—S2	118.56 (10)	F1—C7—F2	109.00 (16)
C4—N1—S1	118.91 (10)	F3—C7—S1	110.98 (13)
S2—N1—S1	122.53 (8)	F1—C7—S1	110.08 (12)
C6—C1—C2	122.17 (15)	F2—C7—S1	108.03 (13)
C6—C1—Cl1	119.27 (13)	F5—C8—F4	110.23 (19)
C2—C1—Cl1	118.56 (13)	F5—C8—F6	109.09 (18)
C1—C2—C3	118.74 (15)	F4—C8—F6	108.97 (16)
C1—C2—H2	120.6	F5—C8—S2	111.24 (13)
C3—C2—H2	120.6	F4—C8—S2	109.37 (13)
C4—C3—C2	119.07 (15)	F6—C8—S2	107.89 (14)
C4—C3—H3	120.5

O4—S2—N1—C4	−155.34 (12)	N1—C4—C5—C6	−179.88 (14)
O3—S2—N1—C4	−20.57 (14)	C2—C1—C6—C5	0.1 (3)
C8—S2—N1—C4	90.75 (13)	Cl1—C1—C6—C5	179.81 (13)
O4—S2—N1—S1	23.61 (12)	C4—C5—C6—C1	−0.4 (2)
O3—S2—N1—S1	158.38 (9)	O2—S1—C7—F3	−40.94 (16)
C8—S2—N1—S1	−90.29 (11)	O1—S1—C7—F3	−173.17 (14)
O2—S1—N1—C4	−151.50 (12)	N1—S1—C7—F3	75.21 (15)
O1—S1—N1—C4	−15.75 (14)	O2—S1—C7—F1	−163.59 (14)
C7—S1—N1—C4	94.75 (13)	O1—S1—C7—F1	64.17 (16)
O2—S1—N1—S2	29.55 (12)	N1—S1—C7—F1	−47.44 (16)
O1—S1—N1—S2	165.30 (9)	O2—S1—C7—F2	77.50 (14)
C7—S1—N1—S2	−84.20 (11)	O1—S1—C7—F2	−54.73 (14)
C6—C1—C2—C3	0.0 (2)	N1—S1—C7—F2	−166.35 (12)
Cl1—C1—C2—C3	−179.66 (12)	O4—S2—C8—F5	−67.64 (18)
C1—C2—C3—C4	0.1 (2)	O3—S2—C8—F5	159.68 (16)
C2—C3—C4—C5	−0.4 (2)	N1—S2—C8—F5	47.42 (18)
C2—C3—C4—N1	−179.97 (14)	O4—S2—C8—F4	170.36 (13)
S2—N1—C4—C5	−102.12 (15)	O3—S2—C8—F4	37.69 (16)
S1—N1—C4—C5	78.89 (17)	N1—S2—C8—F4	−74.58 (15)
S2—N1—C4—C3	77.44 (17)	O4—S2—C8—F6	51.97 (16)
S1—N1—C4—C3	−101.55 (15)	O3—S2—C8—F6	−80.71 (15)
C3—C4—C5—C6	0.6 (2)	N1—S2—C8—F6	167.02 (13)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O3ⁱ	0.95	2.57	3.496 (2)	164
C5—H5···O1ⁱⁱ	0.95	2.59	3.385 (2)	141

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

Experimental details

Crystal data
Chemical formula	C₈H₄ClF₆NO₄S₂
M_r	391.70
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	120
a, b, c (Å)	11.5998 (3), 13.4423 (4), 9.0548 (2)
β (°)	108.014 (2)
V (Å³)	1342.69 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.68
Crystal size (mm)	0.40 × 0.25 × 0.25

Data collection
Diffractometer	Nonius KappaCCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2007)
T_min, T_max	0.821, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	17100, 3047, 2806
R_int	0.023
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.031, 0.082, 1.04
No. of reflections	3047
No. of parameters	199
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.62, −0.41

Computer programs: , DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998), 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
C3—H3···O3ⁱ	0.95	2.57	3.496 (2)	164
C5—H5···O1ⁱⁱ	0.95	2.59	3.385 (2)	141

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

Footnotes

‡Additional correspondence author, e-mail: j.wardell@abdn.ac.uk.

Acknowledgements

The use of the EPSRC X-ray crystallographic service at the University of Southampton, England, and the valuable assistance of the staff there is gratefully acknowledged. JLW acknowledges support from CAPES (Brazil).

References

Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Deprez, P., Guillaume, J., Becker, R., Corbier, A., Didierlaurent, S., Fortin, M., Frechet, D., Hamon, G., Heckman, B., Heitsch, H., Kleeman, H.-W., Vevert, J. P., Vincent, J. C., Wagner, A. & Zhang, J. (1995). J. Med. Chem. 38, 2357–2377. CrossRef CAS PubMed Web of Science Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Greenfield, L. A. & Crosanu, C. (2008). Tetrahedron Lett. 49, 6300–6303. Web of Science CrossRef CAS Google Scholar
Hooft, R. W. W. (1998). COLLECT. Nonius BV, Delft, The Netherlands. Google Scholar
Laali, K. K., Okazaki, T. & Bunge, S. D. (2007). J. Org. Chem. 72, 6758–6762. Web of Science CSD CrossRef PubMed CAS Google Scholar
Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307–326. New York: Academic Press. Google Scholar
Sheldrick, G. M. (2007). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Westrip, S. P. (2010). publCIF. In preparation. Google Scholar
Wulff, W., Peterson, G., Bauta, W., Chan, K. S., Faron, K., Gilbertson, S., Kaesler, R., Yang, D. & Murray, C. (1986). J. Org. Chem. 51, 277–279. CrossRef CAS Web of Science Google Scholar
Zeller, W. E. (2001). In E-EROS Encyclopedia of Reagents for Organic Synthesis. Chichester: Wiley. Google Scholar

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Volume 66| Part 3| March 2010| Pages o506-o507

doi:10.1107/S1600536810003326

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

N-(4-Chloro­phen­yl)-1,1,1-tri­fluoro-N-(tri­fluoro­methyl­sulfon­yl)methane­sulfonamide

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Footnotes

Acknowledgements

References

organic compounds

N-(4-Chlorophenyl)-1,1,1-trifluoro-N-(trifluoromethylsulfonyl)methanesulfonamide