Download citation
Download citation
link to html
The asymmetric unit of the title compound, C7H6FO2S, contains only one half-mol­ecule; a mirror plane passes through F, S, and the methylene C atom, and bisects the benzene ring. The S atom is sp3 hybridized.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806034726/hk2112sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806034726/hk2112Isup2.hkl
Contains datablock I

CCDC reference: 624724

Key indicators

  • Single-crystal X-ray study
  • T = 294 K
  • Mean [sigma](C-C) = 0.007 Å
  • R factor = 0.043
  • wR factor = 0.115
  • Data-to-parameter ratio = 7.8

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT230_ALERT_2_B Hirshfeld Test Diff for S1 - O1 .. 10.76 su
Alert level C PLAT034_ALERT_1_C No Flack Parameter Given. Z .GT. Si, NonCentro . ? PLAT089_ALERT_3_C Poor Data / Parameter Ratio (Zmax .LT. 18) ..... 7.81 PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 7 PLAT764_ALERT_4_C Overcomplete CIF Bond List Detected (Rep/Expd) . 1.11 Ratio
Alert level G REFLT03_ALERT_4_G WARNING: Large fraction of Friedel related reflns may be needed to determine absolute structure From the CIF: _diffrn_reflns_theta_max 25.97 From the CIF: _reflns_number_total 461 Count of symmetry unique reflns 461 Completeness (_total/calc) 100.00% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 0 Fraction of Friedel pairs measured 0.000 Are heavy atom types Z>Si present yes
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 4 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXL97; software used to prepare material for publication: SHELXL97.

Phenylmethanesulfonyl fluoride top
Crystal data top
C7H6FO2SF(000) = 178
Mr = 173.18Dx = 1.460 Mg m3
Orthorhombic, Pmn21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac -2Cell parameters from 236 reflections
a = 9.2880 (19) Åθ = 2.5–25.4°
b = 8.8160 (18) ŵ = 0.37 mm1
c = 4.812 (1) ÅT = 294 K
V = 394.02 (14) Å3Block, colorless
Z = 20.30 × 0.20 × 0.10 mm
Data collection top
Bruker SMART CCD
diffractometer
461 independent reflections
Radiation source: fine-focus sealed tube383 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.025
φ and ω scansθmax = 26.0°, θmin = 2.3°
Absorption correction: multi-scan
(SADABS; Bruker, 2001)
h = 1111
Tmin = 0.897, Tmax = 0.964k = 100
867 measured reflectionsl = 05
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.043H-atom parameters constrained
wR(F2) = 0.115 w = 1/[σ2(Fo2) + (0.0555P)2 + 0.106P]
where P = (Fo2 + 2Fc2)/3
S = 1.10(Δ/σ)max < 0.001
461 reflectionsΔρmax = 0.29 e Å3
59 parametersΔρmin = 0.21 e Å3
1 restraintExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.103 (17)
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*/UeqOcc. (<1)
S10.00001.08611 (15)0.2480 (3)0.0589 (6)
F10.00001.2043 (4)0.0324 (11)0.0974 (16)
O10.1283 (3)1.0952 (3)0.4147 (8)0.0699 (10)
C10.00000.5503 (7)0.6537 (18)0.085 (2)
H10.00000.47010.77920.102*
C20.1279 (6)0.6089 (5)0.5621 (13)0.0768 (14)
H20.21460.57070.62910.092*
C30.1277 (5)0.7243 (5)0.3708 (9)0.0606 (12)
H30.21410.76310.30390.073*
C40.00000.7817 (5)0.2794 (12)0.0412 (11)
C50.00000.9118 (5)0.0698 (12)0.0500 (13)
H50.08380.90550.04650.060*0.50
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0712 (10)0.0563 (8)0.0493 (9)0.0000.0000.0011 (9)
F10.136 (4)0.074 (2)0.082 (3)0.0000.0000.024 (3)
O10.0610 (18)0.083 (2)0.066 (2)0.0078 (15)0.0212 (19)0.0103 (17)
C10.144 (8)0.054 (3)0.057 (4)0.0000.0000.015 (3)
C20.090 (3)0.076 (3)0.064 (3)0.026 (3)0.007 (3)0.011 (3)
C30.063 (3)0.064 (2)0.054 (3)0.0127 (19)0.008 (2)0.007 (2)
C40.055 (3)0.047 (2)0.022 (3)0.0000.0000.002 (3)
C50.060 (3)0.060 (3)0.031 (3)0.0000.0000.001 (3)
Geometric parameters (Å, º) top
S1—O11.439 (3)C2—C31.372 (6)
S1—O1i1.439 (3)C2—H20.9300
S1—F11.471 (4)C3—C41.362 (5)
S1—C51.759 (5)C3—H30.9300
C1—C2i1.369 (6)C4—C3i1.362 (5)
C1—C21.369 (6)C4—C51.527 (7)
C1—H10.9300C5—H50.9600
O1—S1—O1i111.8 (3)C3—C2—H2120.2
O1—S1—F1110.73 (17)C4—C3—C2119.6 (4)
O1i—S1—F1110.73 (17)C4—C3—H3120.2
O1—S1—C5108.68 (16)C2—C3—H3120.2
O1i—S1—C5108.68 (16)C3—C4—C3i121.0 (5)
F1—S1—C5106.0 (3)C3—C4—C5119.5 (3)
C2i—C1—C2120.5 (6)C3i—C4—C5119.5 (3)
C2i—C1—H1119.7C4—C5—S1109.5 (4)
C2—C1—H1119.7C4—C5—H5110.0
C1—C2—C3119.6 (5)S1—C5—H5109.6
C1—C2—H2120.2
C2i—C1—C2—C31.9 (11)C3i—C4—C5—S190.2 (4)
C1—C2—C3—C41.6 (8)O1—S1—C5—C460.97 (17)
C2—C3—C4—C3i1.4 (8)O1i—S1—C5—C460.97 (17)
C2—C3—C4—C5179.1 (4)F1—S1—C5—C4180.000 (2)
C3—C4—C5—S190.2 (4)
Symmetry code: (i) x, y, z.
 

Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds