1-(4-Bromo­phenyl)-2-(2-propenyl­sulfonyl)­ethano­ne

The title compound, C₁₁H₁₁BrO₃S, was prepared by reaction of sodium allyl­sulfinate with p-bromo­phen­acyl bromide to confirm the identity of the former.

Key indicators

• Single-crystal X-ray study
• T = 295 K
• Mean [sigma](C-C) = 0.007 Å
• R factor = 0.034
• wR factor = 0.088
• Data-to-parameter ratio = 14.8

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.91 Ratio
PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          7
PLAT431_ALERT_2_C Short Inter HL..A Contact  Br1    ..  O3      ..       3.21 Ang.

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   3 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
   1 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: MSC/AFC7 Diffractometer Control Software (Molecular Structure Corporation, 1999); cell refinement: MSC/AFC7 Diffractometer Control Software; data reduction: TEXSAN for Windows (Molecular Structure Corporation, 2001); program(s) used to solve structure: TEXSAN for Windows; program(s) used to refine structure: TEXSAN for Windows and SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: TEXSAN for Windows and PLATON (Spek, 2003).

1-(4-bromophenyl)-2-(2-propenylsulfonyl)ethanone

Crystal data

C11H11BrO3S	Z = 2
Mr = 303.17	F(000) = 304
Triclinic, P1	Dx = 1.658 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.7107 Å
a = 5.2868 (13) Å	Cell parameters from 25 reflections
b = 8.5968 (11) Å	θ = 11.9–15.9°
c = 13.878 (2) Å	µ = 3.54 mm^−1
α = 74.39 (19)°	T = 295 K
β = 89.598 (18)°	Needle, pale yellow
γ = 88.87 (1)°	0.25 × 0.10 × 0.04 mm
V = 607.4 (6) Å^3

Data collection

Rigaku AFC7R diffractometer	1185 reflections with I > 2σ(I)
Radiation source: Rigaku rotating anode	Rint = 0.030
Graphite monochromator	θmax = 25.0°, θmin = 2.5°
ω–2θ scans	h = −6→6
Absorption correction: ψ scan (North et al., 1968)	k = 0→10
Tmin = 0.471, Tmax = 0.871	l = −15→16
2298 measured reflections	3 standard reflections every 150 reflections
2142 independent reflections	intensity decay: 1.2%

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.088	H-atom parameters constrained
S = 1.02	w = 1/[σ^2(Fo^2) + (0.0259P)^2] where P = (Fo^2 + 2Fc^2)/3
2142 reflections	(Δ/σ)max = 0.001
145 parameters	Δρmax = 0.29 e Å^−3
0 restraints	Δρmin = −0.29 e Å^−3

Special details

Experimental. The scan width was (0.89 + 0.35tanθ)° with an ω scan speed of 16° per minute (up to 4 scans to achieve I/σ(I) > 15). Stationary background counts were recorded at each end of the scan, and the scan time:background time ratio was 2:1.

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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 > 2σ(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
Br1	−0.30096 (10)	1.00340 (7)	0.37914 (4)	0.0634 (2)
S1	0.3386 (2)	0.39662 (15)	0.14114 (8)	0.0444 (4)
O1	0.2619 (6)	0.5626 (4)	0.1056 (2)	0.0636 (14)
O2	0.6045 (5)	0.3614 (4)	0.1544 (2)	0.0618 (14)
O3	0.4382 (6)	0.3394 (4)	0.3890 (2)	0.0627 (12)
C1	0.1675 (16)	−0.0027 (9)	0.1139 (5)	0.111 (4)
C2	0.3015 (12)	0.1172 (8)	0.0850 (5)	0.085 (3)
C3	0.2159 (9)	0.2899 (6)	0.0589 (3)	0.0538 (19)
C4	0.1832 (8)	0.3112 (5)	0.2564 (3)	0.0424 (17)
C5	0.2601 (8)	0.3943 (5)	0.3354 (3)	0.0417 (17)
C6	0.1175 (8)	0.5406 (5)	0.3439 (3)	0.0381 (16)
C7	−0.0956 (8)	0.6000 (6)	0.2873 (3)	0.0466 (17)
C8	−0.2216 (8)	0.7373 (6)	0.2979 (3)	0.0514 (17)
C9	−0.1328 (8)	0.8141 (5)	0.3650 (3)	0.0446 (17)
C10	0.0784 (9)	0.7576 (6)	0.4224 (3)	0.0499 (17)
C11	0.2017 (8)	0.6211 (6)	0.4115 (3)	0.0513 (17)
H1A	−0.00970	0.01030	0.12140	0.1330*
H1B	0.24200	−0.10800	0.12860	0.1330*
H2	0.47750	0.09740	0.07880	0.1020*
H3A	0.03640	0.29400	0.06190	0.0650*
H3B	0.27020	0.34120	−0.00720	0.0650*
H4A	0.00550	0.32320	0.24660	0.0510*
H4B	0.22730	0.19960	0.27890	0.0510*
H7	−0.15570	0.54610	0.24070	0.0560*
H8	−0.36790	0.77760	0.25910	0.0610*
H10	0.13780	0.81210	0.46880	0.0600*
H11	0.34700	0.58120	0.45100	0.0610*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br1	0.0644 (4)	0.0512 (3)	0.0793 (4)	0.0089 (3)	0.0050 (3)	−0.0263 (3)
S1	0.0434 (7)	0.0511 (8)	0.0405 (7)	−0.0049 (6)	−0.0015 (5)	−0.0152 (6)
O1	0.086 (3)	0.047 (2)	0.054 (2)	−0.0056 (19)	0.0068 (18)	−0.0071 (17)
O2	0.0371 (19)	0.096 (3)	0.058 (2)	−0.0079 (18)	−0.0019 (15)	−0.030 (2)
O3	0.073 (2)	0.063 (2)	0.056 (2)	0.0269 (19)	−0.0254 (19)	−0.0243 (18)
C1	0.158 (8)	0.086 (5)	0.093 (5)	−0.017 (5)	−0.030 (5)	−0.031 (4)
C2	0.092 (5)	0.085 (5)	0.095 (5)	0.000 (4)	−0.020 (4)	−0.053 (4)
C3	0.053 (3)	0.073 (4)	0.043 (3)	−0.007 (3)	−0.007 (2)	−0.028 (3)
C4	0.041 (3)	0.038 (3)	0.050 (3)	−0.002 (2)	−0.001 (2)	−0.015 (2)
C5	0.043 (3)	0.049 (3)	0.033 (3)	−0.001 (2)	0.001 (2)	−0.011 (2)
C6	0.042 (3)	0.038 (3)	0.034 (2)	−0.003 (2)	0.004 (2)	−0.009 (2)
C7	0.042 (3)	0.052 (3)	0.050 (3)	0.002 (2)	−0.008 (2)	−0.021 (2)
C8	0.046 (3)	0.057 (3)	0.055 (3)	0.007 (2)	−0.010 (2)	−0.022 (3)
C9	0.040 (3)	0.043 (3)	0.050 (3)	−0.002 (2)	0.006 (2)	−0.011 (2)
C10	0.061 (3)	0.051 (3)	0.046 (3)	−0.004 (3)	−0.001 (2)	−0.027 (2)
C11	0.049 (3)	0.056 (3)	0.051 (3)	0.006 (3)	−0.012 (2)	−0.018 (3)

Geometric parameters (Å, º)

Br1—C9	1.895 (4)	C9—C10	1.379 (6)
S1—O1	1.430 (4)	C10—C11	1.375 (7)
S1—O2	1.435 (3)	C1—H1A	0.9500
S1—C3	1.778 (5)	C1—H1B	0.9500
S1—C4	1.774 (4)	C2—H2	0.9500
O3—C5	1.211 (5)	C3—H3A	0.9500
C1—C2	1.236 (11)	C3—H3B	0.9500
C2—C3	1.492 (9)	C4—H4A	0.9500
C4—C5	1.522 (6)	C4—H4B	0.9500
C5—C6	1.485 (6)	C7—H7	0.9500
C6—C7	1.386 (6)	C8—H8	0.9500
C6—C11	1.387 (6)	C10—H10	0.9500
C7—C8	1.386 (7)	C11—H11	0.9500
C8—C9	1.368 (6)
Br1···O3^i	3.213 (4)	C8···C1^x	3.575 (9)
Br1···H4B^i	3.1000	C11···C8^iv	3.461 (6)
Br1···H10^ii	3.1000	C11···C11^xi	3.502 (6)
O1···C6	3.345 (5)	C2···H4B	2.9800
O1···C7	3.222 (5)	C4···H7	2.6400
O1···C3^iii	3.406 (5)	C7···H4A	2.6300
O2···C4^iv	3.351 (5)	H1A···H3A	2.3700
O3···Br1^v	3.213 (4)	H2···O2	2.8400
O3···C7^iv	3.398 (6)	H3A···O2^ix	2.7400
O1···H7	2.8700	H3A···H1A	2.3700
O1···H3A^iii	2.8000	H3A···O1^iii	2.8000
O1···H3B^vi	2.8400	H3B···O1^vi	2.8400
O2···H3A^iv	2.7400	H3B···O2^vi	2.9000
O2···H2	2.8400	H4A···O2^ix	2.4500
O2···H3B^vi	2.9000	H4A···C7	2.6300
O2···H4A^iv	2.4500	H4A···H7	2.0600
O2···H7^iv	2.5900	H4B···Br1^v	3.1000
O3···H11	2.4900	H4B···C2	2.9800
O3···H11^vii	2.7500	H7···O1	2.8700
C1···C8^viii	3.575 (9)	H7···O2^ix	2.5900
C3···O1^iii	3.406 (5)	H7···C4	2.6400
C4···O2^ix	3.351 (5)	H7···H4A	2.0600
C6···O1	3.345 (5)	H10···Br1^ii	3.1000
C7···O3^ix	3.398 (6)	H11···O3	2.4900
C7···O1	3.222 (5)	H11···O3^vii	2.7500
C8···C11^ix	3.461 (6)	H11···H11^vii	2.3100
O1—S1—O2	117.5 (5)	C2—C1—H1B	120.00
O1—S1—C3	108.5 (5)	H1A—C1—H1B	120.00
O1—S1—C4	108.6 (5)	C1—C2—H2	117.00
O2—S1—C3	109.0 (5)	C3—C2—H2	117.00
O2—S1—C4	108.5 (5)	S1—C3—H3A	109.00
C3—S1—C4	104.1 (5)	S1—C3—H3B	109.00
C1—C2—C3	126.8 (8)	C2—C3—H3A	109.00
S1—C3—C2	112.8 (6)	C2—C3—H3B	109.00
S1—C4—C5	111.0 (6)	H3A—C3—H3B	109.00
O3—C5—C4	118.6 (6)	S1—C4—H4A	109.00
O3—C5—C6	122.0 (6)	S1—C4—H4B	109.00
C4—C5—C6	119.4 (6)	C5—C4—H4A	109.00
C5—C6—C7	122.9 (6)	C5—C4—H4B	109.00
C5—C6—C11	118.4 (6)	H4A—C4—H4B	109.00
C7—C6—C11	118.7 (7)	C6—C7—H7	120.00
C6—C7—C8	120.6 (7)	C8—C7—H7	120.00
C7—C8—C9	119.2 (6)	C7—C8—H8	120.00
Br1—C9—C8	119.6 (6)	C9—C8—H8	120.00
Br1—C9—C10	118.9 (6)	C9—C10—H10	121.00
C8—C9—C10	121.5 (7)	C11—C10—H10	121.00
C9—C10—C11	118.9 (7)	C6—C11—H11	119.00
C6—C11—C10	121.1 (6)	C10—C11—H11	119.00
C2—C1—H1A	120.00
O1—S1—C3—C2	175.7 (6)	C4—C5—C6—C7	4.5 (8)
O2—S1—C3—C2	46.7 (7)	C5—C6—C7—C8	−179.9 (6)
C4—S1—C3—C2	−68.8 (6)	C11—C6—C7—C8	0.2 (8)
O1—S1—C4—C5	−62.5 (6)	C5—C6—C11—C10	179.7 (6)
O2—S1—C4—C5	66.3 (6)	C7—C6—C11—C10	−0.3 (8)
C3—S1—C4—C5	−177.9 (6)	C6—C7—C8—C9	0.1 (8)
C1—C2—C3—S1	115.0 (9)	C7—C8—C9—C10	−0.2 (8)
S1—C4—C5—O3	−91.4 (7)	C7—C8—C9—Br1	179.3 (6)
S1—C4—C5—C6	87.9 (6)	C8—C9—C10—C11	0.1 (8)
O3—C5—C6—C7	−176.2 (6)	Br1—C9—C10—C11	−179.4 (6)
O3—C5—C6—C11	3.8 (8)	C9—C10—C11—C6	0.2 (8)
C4—C5—C6—C11	−175.5 (6)

Symmetry codes: (i) x−1, y+1, z; (ii) −x, −y+2, −z+1; (iii) −x, −y+1, −z; (iv) x+1, y, z; (v) x+1, y−1, z; (vi) −x+1, −y+1, −z; (vii) −x+1, −y+1, −z+1; (viii) x, y−1, z; (ix) x−1, y, z; (x) x, y+1, z; (xi) −x, −y+1, −z+1.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4A···O2^ix	0.95	2.45	3.351 (5)	157
C7—H7···O2^ix	0.95	2.59	3.511 (6)	164

Symmetry code: (ix) x−1, y, z.