The title compound, C11H11BrO3S, was prepared by reaction of sodium allylsulfinate with p-bromophenacyl bromide to confirm the identity of the former.
Supporting information
CCDC reference: 274325
Key indicators
- Single-crystal X-ray study
- T = 295 K
- Mean (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
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
top
Crystal data top
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) Å3 | |
Data collection top
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 top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.034 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.088 | H-atom parameters constrained |
S = 1.02 | w = 1/[σ2(Fo2) + (0.0259P)2] where P = (Fo2 + 2Fc2)/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 top
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 (Å2) top | 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 (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
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) top
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···O3i | 3.213 (4) | C8···C1x | 3.575 (9) |
Br1···H4Bi | 3.1000 | C11···C8iv | 3.461 (6) |
Br1···H10ii | 3.1000 | C11···C11xi | 3.502 (6) |
O1···C6 | 3.345 (5) | C2···H4B | 2.9800 |
O1···C7 | 3.222 (5) | C4···H7 | 2.6400 |
O1···C3iii | 3.406 (5) | C7···H4A | 2.6300 |
O2···C4iv | 3.351 (5) | H1A···H3A | 2.3700 |
O3···Br1v | 3.213 (4) | H2···O2 | 2.8400 |
O3···C7iv | 3.398 (6) | H3A···O2ix | 2.7400 |
O1···H7 | 2.8700 | H3A···H1A | 2.3700 |
O1···H3Aiii | 2.8000 | H3A···O1iii | 2.8000 |
O1···H3Bvi | 2.8400 | H3B···O1vi | 2.8400 |
O2···H3Aiv | 2.7400 | H3B···O2vi | 2.9000 |
O2···H2 | 2.8400 | H4A···O2ix | 2.4500 |
O2···H3Bvi | 2.9000 | H4A···C7 | 2.6300 |
O2···H4Aiv | 2.4500 | H4A···H7 | 2.0600 |
O2···H7iv | 2.5900 | H4B···Br1v | 3.1000 |
O3···H11 | 2.4900 | H4B···C2 | 2.9800 |
O3···H11vii | 2.7500 | H7···O1 | 2.8700 |
C1···C8viii | 3.575 (9) | H7···O2ix | 2.5900 |
C3···O1iii | 3.406 (5) | H7···C4 | 2.6400 |
C4···O2ix | 3.351 (5) | H7···H4A | 2.0600 |
C6···O1 | 3.345 (5) | H10···Br1ii | 3.1000 |
C7···O3ix | 3.398 (6) | H11···O3 | 2.4900 |
C7···O1 | 3.222 (5) | H11···O3vii | 2.7500 |
C8···C11ix | 3.461 (6) | H11···H11vii | 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) top
D—H···A | D—H | H···A | D···A | D—H···A |
C4—H4A···O2ix | 0.95 | 2.45 | 3.351 (5) | 157 |
C7—H7···O2ix | 0.95 | 2.59 | 3.511 (6) | 164 |
Symmetry code: (ix) x−1, y, z. |