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In the title compound, C7H6FNO4S, the average S—C and S=O bond lengths are 1.762 (2) and 1.4266 (19) Å, respectively. The crystal structure is stabilized by intra- and inter­molecular C—H...O hydrogen bonds.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806048975/rz2092sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806048975/rz2092Isup2.hkl
Contains datablock I

CCDC reference: 630224

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.044
  • wR factor = 0.115
  • Data-to-parameter ratio = 12.5

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for N1 PLAT431_ALERT_2_C Short Inter HL..A Contact F1 .. O2 .. 2.93 Ang.
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 2 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP (Bruker, 2002); software used to prepare material for publication: SHELXL97.

4-Fluoro-3-nitrophenyl methyl sulfone top
Crystal data top
C7H6FNO4SF(000) = 448
Mr = 219.19Dx = 1.636 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 2588 reflections
a = 7.8514 (15) Åθ = 2.7–25.1°
b = 9.7882 (18) ŵ = 0.37 mm1
c = 12.215 (2) ÅT = 298 K
β = 108.595 (3)°Block, colourless
V = 889.8 (3) Å30.38 × 0.31 × 0.30 mm
Z = 4
Data collection top
Bruker APEX area-detector
diffractometer
1603 independent reflections
Radiation source: fine-focus sealed tube1525 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.015
φ and ω scansθmax = 25.2°, θmin = 2.7°
Absorption correction: multi-scan
(SADABS; Bruker, 2002)
h = 59
Tmin = 0.873, Tmax = 0.898k = 1111
4551 measured reflectionsl = 1412
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.044Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.115H-atom parameters constrained
S = 1.13 w = 1/[σ2(Fo2) + (0.0563P)2 + 0.4108P]
where P = (Fo2 + 2Fc2)/3
1603 reflections(Δ/σ)max < 0.001
128 parametersΔρmax = 0.26 e Å3
0 restraintsΔρmin = 0.25 e Å3
Special details top

Experimental. Spectroscopic analysis: 1H NMR (CDCl3, δ, p.p.m.): 8.66–8.69 (m, 1H), 8.22–8.27 (m, 1H), 7.59 (t, 1H), 3.14 (s, 3H).

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
S10.58945 (7)0.19920 (5)0.01371 (5)0.0433 (2)
F10.8607 (2)0.75129 (16)0.03459 (17)0.0730 (5)
O11.0051 (3)0.7317 (2)0.1871 (2)0.0914 (8)
O20.8927 (4)0.5852 (3)0.27171 (19)0.1057 (9)
O30.5782 (3)0.18000 (18)0.09938 (16)0.0630 (5)
O40.4271 (2)0.18760 (19)0.10874 (17)0.0649 (5)
N10.9155 (3)0.6317 (2)0.1867 (2)0.0587 (6)
C10.8032 (3)0.6243 (2)0.0284 (2)0.0465 (5)
C20.8260 (3)0.5627 (2)0.07696 (19)0.0409 (5)
C30.7626 (3)0.4323 (2)0.08157 (17)0.0380 (5)
H30.77780.39020.15230.046*
C40.6765 (3)0.3652 (2)0.02005 (17)0.0368 (5)
C50.6533 (3)0.4269 (2)0.12623 (18)0.0470 (6)
H50.59460.38070.19440.056*
C60.7177 (3)0.5566 (3)0.1296 (2)0.0536 (6)
H60.70350.59870.20020.064*
C70.7502 (4)0.0879 (3)0.0342 (3)0.0668 (8)
H7A0.86190.10030.02680.100*
H7B0.76720.10680.10710.100*
H7C0.71010.00470.03340.100*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0432 (3)0.0362 (3)0.0521 (4)0.0063 (2)0.0175 (3)0.0062 (2)
F10.0786 (11)0.0418 (8)0.1059 (13)0.0099 (8)0.0398 (10)0.0149 (8)
O10.0836 (15)0.0756 (14)0.1075 (19)0.0394 (13)0.0198 (14)0.0332 (13)
O20.162 (3)0.0996 (18)0.0507 (12)0.0459 (18)0.0273 (15)0.0256 (12)
O30.0811 (13)0.0532 (10)0.0635 (11)0.0150 (9)0.0355 (10)0.0036 (8)
O40.0514 (10)0.0615 (12)0.0727 (12)0.0115 (8)0.0069 (9)0.0159 (9)
N10.0572 (12)0.0506 (13)0.0637 (14)0.0069 (10)0.0129 (10)0.0200 (11)
C10.0451 (12)0.0339 (11)0.0659 (15)0.0009 (9)0.0252 (11)0.0079 (10)
C20.0400 (11)0.0370 (11)0.0464 (12)0.0002 (9)0.0146 (9)0.0062 (9)
C30.0425 (11)0.0379 (11)0.0338 (10)0.0022 (9)0.0124 (9)0.0021 (8)
C40.0394 (11)0.0345 (10)0.0371 (11)0.0003 (9)0.0132 (8)0.0007 (8)
C50.0511 (13)0.0537 (14)0.0340 (11)0.0010 (11)0.0105 (9)0.0006 (10)
C60.0619 (15)0.0563 (14)0.0455 (13)0.0069 (12)0.0211 (11)0.0175 (11)
C70.0618 (16)0.0364 (13)0.113 (2)0.0021 (11)0.0433 (16)0.0095 (14)
Geometric parameters (Å, º) top
S1—O31.4244 (19)C2—C31.378 (3)
S1—O41.4287 (18)C3—C41.376 (3)
S1—C71.745 (3)C3—H30.9300
S1—C41.774 (2)C4—C51.389 (3)
F1—C11.333 (3)C5—C61.373 (4)
O1—N11.205 (3)C5—H50.9300
O2—N11.199 (3)C6—H60.9300
N1—C21.465 (3)C7—H7A0.9600
C1—C61.373 (4)C7—H7B0.9600
C1—C21.381 (3)C7—H7C0.9600
O3—S1—O4117.55 (12)C2—C3—H3120.5
O3—S1—C7109.13 (14)C3—C4—C5121.1 (2)
O4—S1—C7109.43 (14)C3—C4—S1118.86 (16)
O3—S1—C4107.88 (10)C5—C4—S1120.07 (16)
O4—S1—C4107.08 (10)C6—C5—C4119.3 (2)
C7—S1—C4105.02 (11)C6—C5—H5120.3
O2—N1—O1123.6 (2)C4—C5—H5120.3
O2—N1—C2117.2 (2)C5—C6—C1119.9 (2)
O1—N1—C2119.2 (2)C5—C6—H6120.1
F1—C1—C6118.4 (2)C1—C6—H6120.1
F1—C1—C2120.9 (2)S1—C7—H7A109.5
C6—C1—C2120.6 (2)S1—C7—H7B109.5
C3—C2—C1120.1 (2)H7A—C7—H7B109.5
C3—C2—N1117.7 (2)S1—C7—H7C109.5
C1—C2—N1122.2 (2)H7A—C7—H7C109.5
C4—C3—C2119.00 (19)H7B—C7—H7C109.5
C4—C3—H3120.5
F1—C1—C2—C3178.8 (2)O3—S1—C4—C317.3 (2)
C6—C1—C2—C30.1 (3)O4—S1—C4—C3144.72 (17)
F1—C1—C2—N10.8 (3)C7—S1—C4—C399.0 (2)
C6—C1—C2—N1179.7 (2)O3—S1—C4—C5161.02 (18)
O2—N1—C2—C316.7 (3)O4—S1—C4—C533.6 (2)
O1—N1—C2—C3164.3 (2)C7—S1—C4—C582.7 (2)
O2—N1—C2—C1162.9 (3)C3—C4—C5—C60.2 (3)
O1—N1—C2—C116.1 (3)S1—C4—C5—C6178.45 (18)
C1—C2—C3—C40.1 (3)C4—C5—C6—C10.4 (4)
N1—C2—C3—C4179.47 (19)F1—C1—C6—C5178.5 (2)
C2—C3—C4—C50.1 (3)C2—C1—C6—C50.4 (4)
C2—C3—C4—S1178.20 (16)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C3—H3···O30.932.542.906 (3)104
C5—H5···O3i0.932.553.379 (3)148
C6—H6···O4ii0.932.393.292 (3)162
Symmetry codes: (i) x, y+1/2, z1/2; (ii) x+1, y+1/2, z1/2.
 

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