N,N-Bis­(tri­fluoro­methyl­sulfonyl)­aniline

The title mol­ecule, C₈H₅F₆NO₄S₂, has crystallographic twofold symmetry. The crystal packing consists of three intermolecular C—H...O contacts, resulting in a two-dimensional network. In the third direction, only a very weak C—H...F interaction, with an H...F distance of 2.83 Å, is found.

Key indicators

• Single-crystal X-ray study
• T = 143 K
• Mean [sigma](C-C) = 0.001 Å
• R factor = 0.026
• wR factor = 0.069
• Data-to-parameter ratio = 25.8

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry

General Notes



ABSTY_01  Extra text has been found in the _exptl_absorpt_correction_type
          field, which should be only a single keyword. A literature
          citation should be included in the _exptl_absorpt_process_details
          field.

REFLT_03
         From the CIF: _diffrn_reflns_theta_max           35.00
         From the CIF: _reflns_number_total               2529
         Count of symmetry unique reflns         1442
         Completeness (_total/calc)            175.38%
         TEST3: Check Friedels for noncentro structure
         Estimate of Friedel pairs measured      1087
         Fraction of Friedel pairs measured     0.754
         Are heavy atom types Z>Si present          yes
          Please check that the estimate of the number of Friedel pairs is
          correct. If it is not, please give the correct count in the
          _publ_section_exptl_refinement section of the submitted CIF.

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Computing details

Data collection: SMART (Siemens, 1995); cell refinement: SMART; data reduction: SAINT (Siemens, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP in SHELXTL (Sheldrick, 1996); software used to prepare material for publication: SHELXL97.

N,N-Bis-(trifluoromethylsulfonyl)-aniline

Crystal data

C8H5F6NO4S2	Dx = 1.863 Mg m^−3
Mr = 357.25	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Fdd2	Cell parameters from 234 reflections
a = 24.871 (4) Å	θ = 3–36°
b = 5.6208 (6) Å	µ = 0.51 mm^−1
c = 18.2216 (19) Å	T = 143 K
V = 2547.3 (6) Å^3	Rod, colorless
Z = 8	0.50 × 0.18 × 0.12 mm
F(000) = 1424

Data collection

Siemens SMART CCD diffractometer	2529 independent reflections
Radiation source: normal-focus sealed tube	2334 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.029
ω scans	θmax = 35.0°, θmin = 2.8°
Absorption correction: numerical (SHELXTL; sheldrick, 1996)	h = −33→39
Tmin = 0.823, Tmax = 0.946	k = −8→9
13534 measured reflections	l = −28→26

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.026	w = 1/[σ^2(Fo^2) + (0.04P)^2] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.069	(Δ/σ)max = 0.001
S = 1.20	Δρmax = 0.29 e Å^−3
2529 reflections	Δρmin = −0.24 e Å^−3
98 parameters	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
1 restraint	Extinction coefficient: 0.00060 (14)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983), 1139 Friedel pairs
Secondary atom site location: difference Fourier map	Absolute structure parameter: 0.00 (5)

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
S	0.045399 (12)	0.33278 (5)	0.157580 (14)	0.02032 (7)
F1	0.12037 (4)	0.6093 (2)	0.10422 (6)	0.0471 (3)
F2	0.08986 (4)	0.72280 (18)	0.20794 (6)	0.0420 (2)
F3	0.14160 (4)	0.41756 (18)	0.20250 (6)	0.0437 (2)
O1	0.02663 (5)	0.2793 (2)	0.22910 (5)	0.0317 (2)
O2	0.06291 (5)	0.15571 (18)	0.10745 (5)	0.0307 (2)
N	0.0000	0.5000	0.11348 (7)	0.0169 (2)
C1	0.0000	0.5000	0.03301 (8)	0.0160 (3)
C2	0.02426 (5)	0.68779 (19)	−0.00387 (6)	0.0185 (2)
H2	0.0405	0.8147	0.0224	0.022*
C3	0.02420 (5)	0.6858 (2)	−0.08032 (6)	0.0220 (2)
H3	0.0408	0.8118	−0.1067	0.026*
C4	0.0000	0.5000	−0.11796 (9)	0.0230 (3)
H4	0.0000	0.5000	−0.1701	0.028*
C5	0.10330 (5)	0.5364 (2)	0.16854 (7)	0.0273 (2)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S	0.02467 (13)	0.01993 (11)	0.01635 (11)	0.00063 (10)	−0.00424 (10)	0.00125 (10)
F1	0.0316 (5)	0.0763 (8)	0.0334 (5)	−0.0213 (5)	−0.0039 (4)	0.0126 (5)
F2	0.0382 (5)	0.0328 (4)	0.0549 (6)	−0.0053 (4)	−0.0085 (4)	−0.0127 (4)
F3	0.0316 (5)	0.0477 (6)	0.0518 (6)	0.0035 (4)	−0.0213 (4)	0.0042 (5)
O1	0.0405 (5)	0.0356 (5)	0.0189 (4)	−0.0034 (4)	−0.0027 (4)	0.0098 (4)
O2	0.0369 (5)	0.0261 (5)	0.0292 (5)	0.0105 (4)	−0.0083 (4)	−0.0076 (4)
N	0.0187 (6)	0.0198 (6)	0.0123 (5)	0.0011 (5)	0.000	0.000
C1	0.0175 (7)	0.0183 (6)	0.0121 (6)	0.0000 (5)	0.000	0.000
C2	0.0207 (5)	0.0171 (5)	0.0177 (5)	−0.0029 (4)	0.0005 (4)	−0.0015 (3)
C3	0.0262 (6)	0.0217 (5)	0.0182 (5)	−0.0022 (4)	0.0039 (4)	0.0031 (4)
C4	0.0305 (9)	0.0238 (7)	0.0147 (6)	−0.0011 (6)	0.000	0.000
C5	0.0240 (6)	0.0333 (6)	0.0246 (6)	−0.0030 (5)	−0.0072 (5)	0.0015 (5)

Geometric parameters (Å, º)

S—O1	1.4164 (10)	C1—C2^i	1.3891 (13)
S—O2	1.4194 (10)	C1—C2	1.3891 (13)
S—N	1.6746 (7)	C2—C3	1.3930 (16)
S—C5	1.8502 (14)	C2—H2	0.9500
F1—C5	1.3122 (17)	C3—C4	1.3867 (15)
F2—C5	1.3134 (17)	C3—H3	0.9500
F3—C5	1.3177 (15)	C4—C3^i	1.3867 (15)
N—C1	1.4664 (18)	C4—H4	0.9500
N—S^i	1.6745 (7)
O1—S—O2	122.99 (7)	C3—C2—H2	120.8
O1—S—N	109.77 (6)	C4—C3—C2	120.08 (12)
O2—S—N	106.96 (6)	C4—C3—H3	120.0
O1—S—C5	106.76 (7)	C2—C3—H3	120.0
O2—S—C5	105.33 (7)	C3^i—C4—C3	120.71 (16)
N—S—C5	103.26 (5)	C3^i—C4—H4	119.6
C1—N—S^i	118.67 (4)	C3—C4—H4	119.6
C1—N—S	118.68 (4)	F1—C5—F2	108.74 (12)
S^i—N—S	122.65 (8)	F1—C5—F3	110.11 (12)
C2^i—C1—C2	122.14 (13)	F2—C5—F3	109.37 (11)
C2^i—C1—N	118.93 (7)	F1—C5—S	110.40 (9)
C2—C1—N	118.93 (7)	F2—C5—S	110.77 (10)
C1—C2—C3	118.50 (11)	F3—C5—S	107.45 (9)
C1—C2—H2	120.8
O1—S—N—C1	−156.60 (5)	C1—C2—C3—C4	0.42 (17)
O2—S—N—C1	−20.99 (6)	C2—C3—C4—C3^i	−0.22 (9)
C5—S—N—C1	89.86 (5)	O1—S—C5—F1	−175.02 (10)
O1—S—N—S^i	23.40 (5)	O2—S—C5—F1	52.74 (11)
O2—S—N—S^i	159.01 (6)	N—S—C5—F1	−59.31 (11)
C5—S—N—S^i	−90.14 (5)	O1—S—C5—F2	−54.52 (11)
S^i—N—C1—C2^i	−100.03 (6)	O2—S—C5—F2	173.25 (10)
S—N—C1—C2^i	79.97 (6)	N—S—C5—F2	61.20 (11)
S^i—N—C1—C2	79.98 (6)	O1—S—C5—F3	64.89 (11)
S—N—C1—C2	−100.03 (6)	O2—S—C5—F3	−67.35 (11)
C2^i—C1—C2—C3	−0.21 (8)	N—S—C5—F3	−179.40 (9)
N—C1—C2—C3	179.79 (8)

Symmetry code: (i) −x, −y+1, z.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O2^ii	0.95	2.53	3.458 (2)	167
C4—H4···O1^iii	0.95	2.51	3.267 (2)	137
C4—H4···O1^iv	0.95	2.51	3.267 (2)	137

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