Phenyl­methane­sulfonyl fluoride

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.

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

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Computing details

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

Crystal data

C7H6FO2S	F(000) = 178
Mr = 173.18	Dx = 1.460 Mg m^−3
Orthorhombic, Pmn21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac -2	Cell parameters from 236 reflections
a = 9.2880 (19) Å	θ = 2.5–25.4°
b = 8.8160 (18) Å	µ = 0.37 mm^−1
c = 4.812 (1) Å	T = 294 K
V = 394.02 (14) Å^3	Block, colorless
Z = 2	0.30 × 0.20 × 0.10 mm

Data collection

Bruker SMART CCD diffractometer	461 independent reflections
Radiation source: fine-focus sealed tube	383 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.025
φ and ω scans	θmax = 26.0°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −11→11
Tmin = 0.897, Tmax = 0.964	k = −10→0
867 measured reflections	l = 0→5

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.043	H-atom parameters constrained
wR(F^2) = 0.115	w = 1/[σ^2(Fo^2) + (0.0555P)^2 + 0.106P] where P = (Fo^2 + 2Fc^2)/3
S = 1.10	(Δ/σ)max < 0.001
461 reflections	Δρmax = 0.29 e Å^−3
59 parameters	Δρmin = −0.21 e Å^−3
1 restraint	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.103 (17)

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	Occ. (<1)
S1	0.0000	1.08611 (15)	0.2480 (3)	0.0589 (6)
F1	0.0000	1.2043 (4)	0.0324 (11)	0.0974 (16)
O1	0.1283 (3)	1.0952 (3)	0.4147 (8)	0.0699 (10)
C1	0.0000	0.5503 (7)	0.6537 (18)	0.085 (2)
H1	0.0000	0.4701	0.7792	0.102*
C2	0.1279 (6)	0.6089 (5)	0.5621 (13)	0.0768 (14)
H2	0.2146	0.5707	0.6291	0.092*
C3	0.1277 (5)	0.7243 (5)	0.3708 (9)	0.0606 (12)
H3	0.2141	0.7631	0.3039	0.073*
C4	0.0000	0.7817 (5)	0.2794 (12)	0.0412 (11)
C5	0.0000	0.9118 (5)	0.0698 (12)	0.0500 (13)
H5	0.0838	0.9055	−0.0465	0.060*	0.50

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0712 (10)	0.0563 (8)	0.0493 (9)	0.000	0.000	−0.0011 (9)
F1	0.136 (4)	0.074 (2)	0.082 (3)	0.000	0.000	0.024 (3)
O1	0.0610 (18)	0.083 (2)	0.066 (2)	−0.0078 (15)	−0.0212 (19)	−0.0103 (17)
C1	0.144 (8)	0.054 (3)	0.057 (4)	0.000	0.000	0.015 (3)
C2	0.090 (3)	0.076 (3)	0.064 (3)	0.026 (3)	−0.007 (3)	0.011 (3)
C3	0.063 (3)	0.064 (2)	0.054 (3)	0.0127 (19)	0.008 (2)	0.007 (2)
C4	0.055 (3)	0.047 (2)	0.022 (3)	0.000	0.000	−0.002 (3)
C5	0.060 (3)	0.060 (3)	0.031 (3)	0.000	0.000	0.001 (3)

Geometric parameters (Å, º)

S1—O1	1.439 (3)	C2—C3	1.372 (6)
S1—O1^i	1.439 (3)	C2—H2	0.9300
S1—F1	1.471 (4)	C3—C4	1.362 (5)
S1—C5	1.759 (5)	C3—H3	0.9300
C1—C2^i	1.369 (6)	C4—C3^i	1.362 (5)
C1—C2	1.369 (6)	C4—C5	1.527 (7)
C1—H1	0.9300	C5—H5	0.9600
O1—S1—O1^i	111.8 (3)	C3—C2—H2	120.2
O1—S1—F1	110.73 (17)	C4—C3—C2	119.6 (4)
O1^i—S1—F1	110.73 (17)	C4—C3—H3	120.2
O1—S1—C5	108.68 (16)	C2—C3—H3	120.2
O1^i—S1—C5	108.68 (16)	C3—C4—C3^i	121.0 (5)
F1—S1—C5	106.0 (3)	C3—C4—C5	119.5 (3)
C2^i—C1—C2	120.5 (6)	C3^i—C4—C5	119.5 (3)
C2^i—C1—H1	119.7	C4—C5—S1	109.5 (4)
C2—C1—H1	119.7	C4—C5—H5	110.0
C1—C2—C3	119.6 (5)	S1—C5—H5	109.6
C1—C2—H2	120.2
C2^i—C1—C2—C3	−1.9 (11)	C3^i—C4—C5—S1	90.2 (4)
C1—C2—C3—C4	1.6 (8)	O1—S1—C5—C4	60.97 (17)
C2—C3—C4—C3^i	−1.4 (8)	O1^i—S1—C5—C4	−60.97 (17)
C2—C3—C4—C5	179.1 (4)	F1—S1—C5—C4	180.000 (2)
C3—C4—C5—S1	−90.2 (4)

Symmetry code: (i) −x, y, z.