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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.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680200764X/na6160sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S160053680200764X/na6160Isup2.hkl
Contains datablock I

CCDC reference: 189309

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.

Computing details top

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 top
Crystal data top
C8H5F6NO4S2Dx = 1.863 Mg m3
Mr = 357.25Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Fdd2Cell parameters from 234 reflections
a = 24.871 (4) Åθ = 3–36°
b = 5.6208 (6) ŵ = 0.51 mm1
c = 18.2216 (19) ÅT = 143 K
V = 2547.3 (6) Å3Rod, colorless
Z = 80.50 × 0.18 × 0.12 mm
F(000) = 1424
Data collection top
Siemens SMART CCD
diffractometer
2529 independent reflections
Radiation source: normal-focus sealed tube2334 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.029
ω scansθmax = 35.0°, θmin = 2.8°
Absorption correction: numerical (SHELXTL; sheldrick, 1996)h = 3339
Tmin = 0.823, Tmax = 0.946k = 89
13534 measured reflectionsl = 2826
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.026 w = 1/[σ2(Fo2) + (0.04P)2]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.069(Δ/σ)max = 0.001
S = 1.20Δρmax = 0.29 e Å3
2529 reflectionsΔρmin = 0.24 e Å3
98 parametersExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
1 restraintExtinction coefficient: 0.00060 (14)
Primary atom site location: structure-invariant direct methodsAbsolute structure: Flack (1983), 1139 Friedel pairs
Secondary atom site location: difference Fourier mapAbsolute structure parameter: 0.00 (5)
Special details top

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 (Å2) top
xyzUiso*/Ueq
S0.045399 (12)0.33278 (5)0.157580 (14)0.02032 (7)
F10.12037 (4)0.6093 (2)0.10422 (6)0.0471 (3)
F20.08986 (4)0.72280 (18)0.20794 (6)0.0420 (2)
F30.14160 (4)0.41756 (18)0.20250 (6)0.0437 (2)
O10.02663 (5)0.2793 (2)0.22910 (5)0.0317 (2)
O20.06291 (5)0.15571 (18)0.10745 (5)0.0307 (2)
N0.00000.50000.11348 (7)0.0169 (2)
C10.00000.50000.03301 (8)0.0160 (3)
C20.02426 (5)0.68779 (19)0.00387 (6)0.0185 (2)
H20.04050.81470.02240.022*
C30.02420 (5)0.6858 (2)0.08032 (6)0.0220 (2)
H30.04080.81180.10670.026*
C40.00000.50000.11796 (9)0.0230 (3)
H40.00000.50000.17010.028*
C50.10330 (5)0.5364 (2)0.16854 (7)0.0273 (2)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S0.02467 (13)0.01993 (11)0.01635 (11)0.00063 (10)0.00424 (10)0.00125 (10)
F10.0316 (5)0.0763 (8)0.0334 (5)0.0213 (5)0.0039 (4)0.0126 (5)
F20.0382 (5)0.0328 (4)0.0549 (6)0.0053 (4)0.0085 (4)0.0127 (4)
F30.0316 (5)0.0477 (6)0.0518 (6)0.0035 (4)0.0213 (4)0.0042 (5)
O10.0405 (5)0.0356 (5)0.0189 (4)0.0034 (4)0.0027 (4)0.0098 (4)
O20.0369 (5)0.0261 (5)0.0292 (5)0.0105 (4)0.0083 (4)0.0076 (4)
N0.0187 (6)0.0198 (6)0.0123 (5)0.0011 (5)0.0000.000
C10.0175 (7)0.0183 (6)0.0121 (6)0.0000 (5)0.0000.000
C20.0207 (5)0.0171 (5)0.0177 (5)0.0029 (4)0.0005 (4)0.0015 (3)
C30.0262 (6)0.0217 (5)0.0182 (5)0.0022 (4)0.0039 (4)0.0031 (4)
C40.0305 (9)0.0238 (7)0.0147 (6)0.0011 (6)0.0000.000
C50.0240 (6)0.0333 (6)0.0246 (6)0.0030 (5)0.0072 (5)0.0015 (5)
Geometric parameters (Å, º) top
S—O11.4164 (10)C1—C2i1.3891 (13)
S—O21.4194 (10)C1—C21.3891 (13)
S—N1.6746 (7)C2—C31.3930 (16)
S—C51.8502 (14)C2—H20.9500
F1—C51.3122 (17)C3—C41.3867 (15)
F2—C51.3134 (17)C3—H30.9500
F3—C51.3177 (15)C4—C3i1.3867 (15)
N—C11.4664 (18)C4—H40.9500
N—Si1.6745 (7)
O1—S—O2122.99 (7)C3—C2—H2120.8
O1—S—N109.77 (6)C4—C3—C2120.08 (12)
O2—S—N106.96 (6)C4—C3—H3120.0
O1—S—C5106.76 (7)C2—C3—H3120.0
O2—S—C5105.33 (7)C3i—C4—C3120.71 (16)
N—S—C5103.26 (5)C3i—C4—H4119.6
C1—N—Si118.67 (4)C3—C4—H4119.6
C1—N—S118.68 (4)F1—C5—F2108.74 (12)
Si—N—S122.65 (8)F1—C5—F3110.11 (12)
C2i—C1—C2122.14 (13)F2—C5—F3109.37 (11)
C2i—C1—N118.93 (7)F1—C5—S110.40 (9)
C2—C1—N118.93 (7)F2—C5—S110.77 (10)
C1—C2—C3118.50 (11)F3—C5—S107.45 (9)
C1—C2—H2120.8
O1—S—N—C1156.60 (5)C1—C2—C3—C40.42 (17)
O2—S—N—C120.99 (6)C2—C3—C4—C3i0.22 (9)
C5—S—N—C189.86 (5)O1—S—C5—F1175.02 (10)
O1—S—N—Si23.40 (5)O2—S—C5—F152.74 (11)
O2—S—N—Si159.01 (6)N—S—C5—F159.31 (11)
C5—S—N—Si90.14 (5)O1—S—C5—F254.52 (11)
Si—N—C1—C2i100.03 (6)O2—S—C5—F2173.25 (10)
S—N—C1—C2i79.97 (6)N—S—C5—F261.20 (11)
Si—N—C1—C279.98 (6)O1—S—C5—F364.89 (11)
S—N—C1—C2100.03 (6)O2—S—C5—F367.35 (11)
C2i—C1—C2—C30.21 (8)N—S—C5—F3179.40 (9)
N—C1—C2—C3179.79 (8)
Symmetry code: (i) x, y+1, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C2—H2···O2ii0.952.533.458 (2)167
C4—H4···O1iii0.952.513.267 (2)137
C4—H4···O1iv0.952.513.267 (2)137
Symmetry codes: (ii) x, y+1, z; (iii) x, y+1/2, z1/2; (iv) x, y+1/2, z1/2.
 

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