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In the title compound, C8H9BrO3S, the six-membered ring has a boat conformation, the two O-containing five-membered rings have envelope conformations and the tetra­hydro­thio­phene ring has a twist conformation. The mol­ecules are linked only by weak van der Waals inter­actions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680603090X/bt2156sup1.cif
Contains datablocks global, 2

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S160053680603090X/bt21562sup2.hkl
Contains datablock 2

CCDC reference: 600522

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.006 Å
  • R factor = 0.035
  • wR factor = 0.069
  • Data-to-parameter ratio = 14.0

checkCIF/PLATON results

No syntax errors found



Alert level C RINTA01_ALERT_3_C The value of Rint is greater than 0.10 Rint given 0.102 PLAT020_ALERT_3_C The value of Rint is greater than 0.10 ......... 0.10 PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT164_ALERT_4_C Nr. of Refined C-H H-Atoms in Heavy-At Struct... 3
Alert level G PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 5 ALERT level C = Check and explain 2 ALERT level G = General alerts; check 3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 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: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

5-Bromo-10-oxa-3-thiatricyclo[5.2.1.01,5]dec-8-ene 3,3-dioxide top
Crystal data top
C8H9BrO3SDx = 1.899 Mg m3
Mr = 265.12Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, PbcaCell parameters from 1326 reflections
a = 10.1723 (6) Åθ = 2.0–27.2°
b = 10.3446 (9) ŵ = 4.63 mm1
c = 17.6278 (10) ÅT = 293 K
V = 1854.9 (2) Å3Plate, colorless
Z = 80.50 × 0.27 × 0.03 mm
F(000) = 1056
Data collection top
Stoe IPDS-2
diffractometer
1823 independent reflections
Radiation source: fine-focus sealed tube1370 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.102
Detector resolution: 6.67 pixels mm-1θmax = 26.0°, θmin = 2.3°
ω scansh = 1212
Absorption correction: integration
(X-RED32; Stoe & Cie, 2002)
k = 1212
Tmin = 0.232, Tmax = 0.870l = 2121
12215 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.035Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.069H atoms treated by a mixture of independent and constrained refinement
S = 0.95 w = 1/[σ2(Fo2) + (0.024P)2 + 1.8112P]
where P = (Fo2 + 2Fc2)/3
1823 reflections(Δ/σ)max = 0.001
130 parametersΔρmax = 0.30 e Å3
0 restraintsΔρmin = 0.34 e Å3
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*/Ueq
C10.3675 (3)0.3491 (3)0.1318 (2)0.0289 (8)
C20.2726 (4)0.3455 (4)0.0635 (2)0.0405 (10)
H2A0.30710.39340.02060.049*
H2B0.18640.37870.07670.049*
C30.2693 (5)0.1977 (5)0.0478 (3)0.0471 (11)
C40.3972 (5)0.1597 (5)0.0135 (3)0.0549 (12)
C50.4847 (5)0.1633 (4)0.0686 (2)0.0457 (10)
C60.4096 (3)0.2027 (4)0.1384 (2)0.0299 (8)
C70.4602 (3)0.1737 (4)0.2160 (2)0.0332 (8)
H7A0.55460.18610.21810.040*
H7B0.44040.08510.22990.040*
C80.3031 (3)0.3825 (4)0.2069 (2)0.0320 (8)
H8A0.20950.36530.20470.038*
H8B0.31590.47330.21840.038*
O10.2818 (2)0.1473 (3)0.12498 (16)0.0391 (6)
O20.2803 (2)0.2182 (3)0.32180 (17)0.0499 (8)
O30.4752 (2)0.3582 (3)0.31915 (16)0.0462 (7)
S10.37909 (8)0.28371 (10)0.27840 (5)0.0321 (2)
Br10.52124 (3)0.46010 (4)0.11588 (2)0.04199 (13)
H30.189 (4)0.169 (5)0.029 (3)0.054 (13)*
H50.579 (5)0.146 (6)0.064 (3)0.090 (18)*
H40.411 (5)0.146 (6)0.037 (3)0.084 (18)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0339 (16)0.0251 (18)0.028 (2)0.0026 (13)0.0025 (13)0.0019 (16)
C20.054 (2)0.034 (2)0.034 (2)0.0027 (17)0.0133 (17)0.006 (2)
C30.067 (3)0.037 (2)0.037 (2)0.009 (2)0.021 (2)0.004 (2)
C40.094 (3)0.037 (3)0.034 (3)0.004 (2)0.001 (2)0.004 (2)
C50.065 (3)0.033 (2)0.039 (2)0.0075 (19)0.008 (2)0.0047 (19)
C60.0298 (16)0.0276 (18)0.032 (2)0.0026 (13)0.0030 (13)0.0005 (16)
C70.0319 (16)0.0326 (18)0.035 (2)0.0047 (15)0.0018 (15)0.0006 (17)
C80.0295 (16)0.032 (2)0.035 (2)0.0062 (15)0.0021 (14)0.0032 (17)
O10.0431 (13)0.0319 (14)0.0424 (17)0.0123 (11)0.0107 (12)0.0061 (14)
O20.0367 (14)0.065 (2)0.0477 (19)0.0016 (14)0.0138 (11)0.0171 (17)
O30.0441 (13)0.0552 (18)0.0392 (16)0.0045 (14)0.0098 (12)0.0080 (15)
S10.0286 (4)0.0399 (5)0.0278 (4)0.0006 (4)0.0012 (3)0.0033 (5)
Br10.0454 (2)0.0385 (2)0.0421 (2)0.01290 (17)0.00634 (17)0.0009 (2)
Geometric parameters (Å, º) top
C1—C81.517 (5)C5—C61.504 (5)
C1—C21.542 (5)C5—H50.98 (5)
C1—C61.578 (5)C6—O11.440 (4)
C1—Br11.961 (3)C6—C71.492 (5)
C2—C31.554 (6)C7—S11.785 (4)
C2—H2A0.9700C7—H7A0.9700
C2—H2B0.9700C7—H7B0.9700
C3—O11.463 (5)C8—S11.797 (4)
C3—C41.487 (7)C8—H8A0.9700
C3—H30.93 (4)C8—H8B0.9700
C4—C51.318 (7)O2—S11.433 (3)
C4—H40.91 (6)O3—S11.437 (3)
C8—C1—C2114.6 (3)O1—C6—C5102.5 (3)
C8—C1—C6105.7 (3)C7—C6—C5121.3 (3)
C2—C1—C6101.8 (3)O1—C6—C197.2 (2)
C8—C1—Br1109.6 (2)C7—C6—C1110.8 (3)
C2—C1—Br1113.7 (3)C5—C6—C1109.7 (3)
C6—C1—Br1110.8 (2)C6—C7—S1106.1 (2)
C1—C2—C3100.1 (3)C6—C7—H7A110.5
C1—C2—H2A111.7S1—C7—H7A110.5
C3—C2—H2A111.7C6—C7—H7B110.5
C1—C2—H2B111.7S1—C7—H7B110.5
C3—C2—H2B111.7H7A—C7—H7B108.7
H2A—C2—H2B109.5C1—C8—S1107.3 (2)
O1—C3—C4102.0 (3)C1—C8—H8A110.3
O1—C3—C2100.6 (3)S1—C8—H8A110.3
C4—C3—C2108.3 (4)C1—C8—H8B110.3
O1—C3—H3107 (3)S1—C8—H8B110.3
C4—C3—H3123 (3)H8A—C8—H8B108.5
C2—C3—H3113 (3)C6—O1—C395.1 (3)
C5—C4—C3106.5 (4)O2—S1—O3117.62 (18)
C5—C4—H4128 (3)O2—S1—C7110.6 (2)
C3—C4—H4125 (3)O3—S1—C7109.59 (16)
C4—C5—C6105.5 (4)O2—S1—C8110.00 (16)
C4—C5—H5127 (4)O3—S1—C8109.77 (19)
C6—C5—H5128 (4)C7—S1—C897.41 (17)
O1—C6—C7112.5 (3)
C8—C1—C2—C3109.4 (4)Br1—C1—C6—C556.7 (3)
C6—C1—C2—C34.2 (4)O1—C6—C7—S179.1 (3)
Br1—C1—C2—C3123.5 (3)C5—C6—C7—S1159.2 (3)
C1—C2—C3—O133.9 (4)C1—C6—C7—S128.4 (3)
C1—C2—C3—C472.6 (4)C2—C1—C8—S1141.4 (3)
O1—C3—C4—C532.3 (5)C6—C1—C8—S130.1 (3)
C2—C3—C4—C573.2 (5)Br1—C1—C8—S189.4 (2)
C3—C4—C5—C60.7 (5)C7—C6—O1—C3179.2 (3)
C4—C5—C6—O131.8 (4)C5—C6—O1—C348.9 (3)
C4—C5—C6—C7158.1 (4)C1—C6—O1—C363.2 (3)
C4—C5—C6—C170.6 (4)C4—C3—O1—C649.3 (4)
C8—C1—C6—O178.6 (3)C2—C3—O1—C662.2 (3)
C2—C1—C6—O141.5 (3)C6—C7—S1—O2105.8 (3)
Br1—C1—C6—O1162.7 (2)C6—C7—S1—O3122.9 (2)
C8—C1—C6—C738.8 (3)C6—C7—S1—C88.8 (3)
C2—C1—C6—C7158.8 (3)C1—C8—S1—O2128.5 (3)
Br1—C1—C6—C779.9 (3)C1—C8—S1—O3100.6 (3)
C8—C1—C6—C5175.3 (3)C1—C8—S1—C713.4 (3)
C2—C1—C6—C564.6 (4)
 

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