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The mol­ecules of the title compound, C15H13BrO3S, are almost planar and do not show unusual geometric parameters. The crystal packing is characterized by short C—H...O contacts.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806033563/hb2128sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806033563/hb2128Isup2.hkl
Contains datablock I

CCDC reference: 621338

Key indicators

  • Single-crystal X-ray study
  • T = 173 K
  • Mean [sigma](C-C) = 0.009 Å
  • R factor = 0.067
  • wR factor = 0.181
  • Data-to-parameter ratio = 14.2

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.96 PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 9 PLAT431_ALERT_2_C Short Inter HL..A Contact Br1 .. O18 .. 3.22 Ang.
Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 27.07 From the CIF: _reflns_number_total 2604 Count of symmetry unique reflns 1688 Completeness (_total/calc) 154.27% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 916 Fraction of Friedel pairs measured 0.543 Are heavy atom types Z>Si present yes
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 0 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 1 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: X-AREA (Stoe & Cie, 2001); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97.

; top
Crystal data top
C15H13BrO3SF(000) = 356
Mr = 353.22Dx = 1.624 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ybCell parameters from 4269 reflections
a = 5.2240 (5) Åθ = 3.9–27.2°
b = 9.3265 (14) ŵ = 2.99 mm1
c = 14.8968 (16) ÅT = 173 K
β = 95.622 (9)°Block, yellow
V = 722.31 (15) Å30.36 × 0.33 × 0.32 mm
Z = 2
Data collection top
STOE IPDS II two-circle-
diffractometer
2604 independent reflections
Radiation source: fine-focus sealed tube2465 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.052
ω scansθmax = 27.1°, θmin = 3.9°
Absorption correction: multi-scan
MULABS (Spek, 2003; Blessing, 1995)
h = 66
Tmin = 0.362, Tmax = 0.398k = 911
4264 measured reflectionsl = 1818
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)] = 0.067H-atom parameters constrained
wR(F2) = 0.181 w = 1/[σ2(Fo2) + (0.1481P)2 + 0.1692P]
where P = (Fo2 + 2Fc2)/3
S = 1.06(Δ/σ)max < 0.001
2604 reflectionsΔρmax = 1.14 e Å3
183 parametersΔρmin = 1.75 e Å3
1 restraintAbsolute structure: Flack (1983), 926 Friedel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.025 (18)
Special details top

Experimental. ;

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
Br11.09630 (12)0.81513 (9)0.68278 (4)0.0350 (2)
S11.4130 (3)0.7167 (2)0.96232 (12)0.0311 (4)
C11.2067 (10)0.6933 (7)0.8656 (4)0.0233 (12)
C21.2728 (11)0.7872 (7)0.7994 (5)0.0270 (14)
C31.4884 (13)0.8753 (9)0.8266 (6)0.0376 (17)
H31.55900.94440.78920.045*
C41.5812 (12)0.8470 (8)0.9144 (6)0.0356 (18)
H41.72430.89530.94500.043*
C51.0062 (10)0.5797 (7)0.8720 (4)0.0213 (12)
O50.9973 (8)0.5182 (6)0.9453 (3)0.0306 (11)
C60.8324 (11)0.5413 (8)0.7922 (4)0.0241 (12)
H60.86140.57820.73460.029*
C70.6320 (10)0.4535 (7)0.8009 (4)0.0208 (11)
H70.60650.42170.85990.025*
C110.4479 (10)0.4026 (6)0.7258 (4)0.0199 (11)
C120.2620 (10)0.2964 (7)0.7433 (4)0.0235 (13)
C130.0862 (11)0.2487 (9)0.6719 (5)0.0323 (16)
H130.03920.17880.68300.039*
C140.0942 (10)0.3021 (9)0.5865 (4)0.0294 (14)
H140.02510.26860.53880.035*
C150.2793 (11)0.4068 (8)0.5687 (4)0.0248 (13)
C160.4514 (11)0.4560 (7)0.6388 (5)0.0228 (12)
H160.57360.52740.62720.027*
O170.2671 (9)0.2485 (6)0.8297 (4)0.0340 (12)
C170.0607 (13)0.1581 (8)0.8519 (5)0.0305 (14)
H17A0.10360.20740.83700.046*
H17B0.08210.13630.91660.046*
H17C0.06250.06870.81740.046*
O180.2698 (10)0.4542 (8)0.4806 (4)0.0434 (15)
C180.4678 (14)0.5515 (11)0.4598 (5)0.0383 (18)
H18A0.45320.64080.49360.057*
H18B0.44900.57210.39500.057*
H18C0.63650.50800.47660.057*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.0486 (4)0.0279 (4)0.0266 (4)0.0057 (3)0.0056 (2)0.0030 (3)
S10.0256 (6)0.0385 (10)0.0267 (8)0.0033 (6)0.0104 (5)0.0117 (7)
C10.020 (2)0.025 (3)0.024 (3)0.001 (2)0.0054 (19)0.007 (3)
C20.031 (3)0.020 (4)0.030 (3)0.003 (2)0.002 (2)0.007 (3)
C30.030 (3)0.033 (4)0.049 (5)0.006 (3)0.000 (3)0.003 (4)
C40.026 (3)0.029 (5)0.049 (4)0.003 (2)0.009 (2)0.016 (3)
C50.023 (2)0.025 (3)0.015 (3)0.003 (2)0.0044 (18)0.002 (2)
O50.033 (2)0.033 (3)0.025 (3)0.0001 (18)0.0062 (17)0.002 (2)
C60.027 (3)0.025 (3)0.018 (3)0.001 (2)0.006 (2)0.006 (3)
C70.023 (2)0.019 (3)0.019 (3)0.002 (2)0.002 (2)0.000 (2)
C110.022 (2)0.009 (3)0.029 (3)0.0007 (18)0.000 (2)0.001 (2)
C120.027 (2)0.016 (4)0.027 (3)0.000 (2)0.0017 (19)0.003 (3)
C130.026 (3)0.032 (4)0.037 (4)0.006 (2)0.005 (2)0.001 (3)
C140.029 (3)0.031 (4)0.026 (3)0.008 (3)0.0061 (19)0.009 (3)
C150.028 (2)0.024 (3)0.021 (3)0.000 (2)0.003 (2)0.000 (3)
C160.025 (2)0.019 (3)0.024 (3)0.000 (2)0.005 (2)0.000 (2)
O170.037 (2)0.036 (3)0.029 (3)0.011 (2)0.0007 (18)0.007 (2)
C170.034 (3)0.025 (4)0.033 (4)0.001 (2)0.006 (2)0.004 (3)
O180.044 (3)0.063 (4)0.021 (3)0.014 (3)0.007 (2)0.007 (3)
C180.040 (3)0.048 (5)0.027 (4)0.002 (3)0.002 (3)0.014 (4)
Geometric parameters (Å, º) top
Br1—C21.903 (7)C12—O171.361 (8)
S1—C41.698 (8)C12—C131.407 (9)
S1—C11.726 (6)C13—C141.371 (11)
C1—C21.388 (10)C13—H130.9500
C1—C51.499 (9)C14—C151.418 (9)
C2—C31.421 (9)C14—H140.9500
C3—C41.375 (12)C15—O181.380 (9)
C3—H30.9500C15—C161.388 (8)
C4—H40.9500C16—H160.9500
C5—O51.239 (8)O17—C171.433 (8)
C5—C61.467 (7)C17—H17A0.9800
C6—C71.345 (9)C17—H17B0.9800
C6—H60.9500C17—H17C0.9800
C7—C111.481 (8)O18—C181.433 (10)
C7—H70.9500C18—H18A0.9800
C11—C161.390 (9)C18—H18B0.9800
C11—C121.428 (8)C18—H18C0.9800
C4—S1—C192.6 (3)C13—C12—C11119.1 (6)
C2—C1—C5135.6 (6)C14—C13—C12120.6 (6)
C2—C1—S1109.6 (4)C14—C13—H13119.7
C5—C1—S1114.8 (5)C12—C13—H13119.7
C1—C2—C3114.0 (6)C13—C14—C15120.5 (6)
C1—C2—Br1127.1 (4)C13—C14—H14119.8
C3—C2—Br1118.8 (6)C15—C14—H14119.8
C4—C3—C2110.9 (7)O18—C15—C16124.8 (6)
C4—C3—H3124.6O18—C15—C14115.9 (6)
C2—C3—H3124.6C16—C15—C14119.3 (6)
C3—C4—S1112.9 (5)C15—C16—C11121.1 (6)
C3—C4—H4123.6C15—C16—H16119.4
S1—C4—H4123.6C11—C16—H16119.4
O5—C5—C6121.8 (6)C12—O17—C17117.8 (5)
O5—C5—C1118.0 (5)O17—C17—H17A109.5
C6—C5—C1120.1 (6)O17—C17—H17B109.5
C7—C6—C5119.8 (6)H17A—C17—H17B109.5
C7—C6—H6120.1O17—C17—H17C109.5
C5—C6—H6120.1H17A—C17—H17C109.5
C6—C7—C11125.2 (6)H17B—C17—H17C109.5
C6—C7—H7117.4C15—O18—C18116.7 (6)
C11—C7—H7117.4O18—C18—H18A109.5
C16—C11—C12119.3 (5)O18—C18—H18B109.5
C16—C11—C7121.5 (5)H18A—C18—H18B109.5
C12—C11—C7119.2 (6)O18—C18—H18C109.5
O17—C12—C13124.2 (6)H18A—C18—H18C109.5
O17—C12—C11116.7 (6)H18B—C18—H18C109.5
C4—S1—C1—C20.3 (5)C6—C7—C11—C12172.7 (6)
C4—S1—C1—C5179.2 (5)C16—C11—C12—O17179.8 (6)
C5—C1—C2—C3178.8 (7)C7—C11—C12—O170.0 (8)
S1—C1—C2—C30.6 (8)C16—C11—C12—C130.1 (9)
C5—C1—C2—Br14.9 (11)C7—C11—C12—C13179.6 (6)
S1—C1—C2—Br1175.7 (4)O17—C12—C13—C14179.8 (7)
C1—C2—C3—C40.6 (10)C11—C12—C13—C140.6 (11)
Br1—C2—C3—C4176.0 (5)C12—C13—C14—C150.3 (12)
C2—C3—C4—S10.3 (9)C13—C14—C15—O18179.6 (7)
C1—S1—C4—C30.0 (6)C13—C14—C15—C160.6 (11)
C2—C1—C5—O5177.4 (7)O18—C15—C16—C11180.0 (6)
S1—C1—C5—O53.3 (8)C14—C15—C16—C111.1 (10)
C2—C1—C5—C64.3 (11)C12—C11—C16—C150.7 (9)
S1—C1—C5—C6175.1 (5)C7—C11—C16—C15179.5 (6)
O5—C5—C6—C710.5 (10)C13—C12—O17—C178.5 (10)
C1—C5—C6—C7171.2 (6)C11—C12—O17—C17171.1 (6)
C5—C6—C7—C11177.8 (5)C16—C15—O18—C185.9 (11)
C6—C7—C11—C167.5 (10)C14—C15—O18—C18175.2 (7)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C4—H4···O5i0.952.373.296 (8)164
C17—H17B···O5ii0.982.413.331 (9)157
C7—H7···O50.952.472.798 (8)100
C7—H7···O170.952.412.763 (8)102
Symmetry codes: (i) x+3, y+1/2, z+2; (ii) x+1, y1/2, z+2.
 

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