N-(4-Chloro-phen-yl)-1,1,1-trifluoro-N-(trifluoro-methyl-sulfon-yl)methane-sulfonamide.

The title mol-ecule, also called 4-chloro-N,N-bis-(trifluoro-methane-sulfon-yl)aniline, C(8)H(4)ClF(6)NO(4)S(2), has non-crystallographic twofold symmetry with the pseudo-axis aligned along the Cl-C⋯C-N backbone of the mol-ecule: the SO(2)CF(3) 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 {⋯HC(2)NSO}(2) synthons within a supra-molecular chain aligned along [101].

Related literature

For uses of N,n class="Chemical">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 = 391.70

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.031

wR(F 2) = 0.082

S = 1.04

3047 reflections

199 parameters

H-atom parameters constrained

Δρmax = 0.62 e Å−3

Δρmin = −0.41 e Å−3

Data collection: COLLECT (Hooft, 1998 ▶); cell refinement: DENZO (Otwinowski & Minor, 1997 ▶) and COLLECT; data reduction: DEn class="Chemical">NZO 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 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810003326/hb5319sup1.cif

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

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

C8H4ClF6NO4S2	F(000) = 776
Mr = 391.70	Dx = 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

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	Rint = 0.023
Detector resolution: 9.091 pixels mm-1	θmax = 27.5°, θmin = 2.9°
φ and ω scans	h = −15→15
Absorption correction: multi-scan (SADABS; Sheldrick, 2007)	k = −17→17
Tmin = 0.821, Tmax = 1.000	l = −11→11
17100 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)] = 0.031	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.082	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0407P)2 + 1.1662P] where P = (Fo2 + 2Fc2)/3
3047 reflections	(Δ/σ)max = 0.001
199 parameters	Δρmax = 0.62 e Å−3
0 restraints	Δρmin = −0.41 e Å−3

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.

	x	y	z	Uiso*/Ueq
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)

	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)

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)

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

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) ; (ii) .