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The title compound, C6H3Br3O2, possesses normal geometrical parameters. The crystal packing is controlled by bifurcated O—H...(Br,Br) and O—H...(O,Br) hydrogen bonds and possible weak π–π stacking interactions, resulting in a chiral structure containing a herring-bone-like motif of constituent mol­ecules.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804000571/fl6075sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804000571/fl6075Isup2.hkl
Contains datablock I

CCDC reference: 234873

Key indicators

  • Single-crystal X-ray study
  • T = 120 K
  • Mean [sigma](C-C) = 0.009 Å
  • R factor = 0.038
  • wR factor = 0.056
  • Data-to-parameter ratio = 17.0

checkCIF/PLATON results

No syntax errors found



Alert level C 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 .. Br2 = 3.51 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 27.44 From the CIF: _reflns_number_total 1820 Count of symmetry unique reflns 1118 Completeness (_total/calc) 162.79% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 702 Fraction of Friedel pairs measured 0.628 Are heavy atom types Z>Si present yes
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 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 1 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: COLLECT (Nonius, 1998); cell refinement: HKL SCALEPACK (Otwinowski & Minor 1997); data reduction: HKL DENZO and SCALEPACK (Otwinowski & Minor 1997) and SORTAV (Blessing, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97.

(I) top
Crystal data top
C6H3Br3O2Dx = 2.853 Mg m3
Mr = 346.81Melting point: 280 K
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 12216 reflections
a = 4.1071 (3) Åθ = 2.9–27.5°
b = 12.855 (1) ŵ = 14.93 mm1
c = 15.296 (1) ÅT = 120 K
V = 807.6 (1) Å3Needle, colourless
Z = 40.38 × 0.04 × 0.03 mm
F(000) = 640
Data collection top
Enraf-Nonius KappaCCD
diffractometer
1820 independent reflections
Radiation source: fine-focus sealed tube1390 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.066
ω and φ scansθmax = 27.4°, θmin = 3.1°
Absorption correction: multi-scan
(SORTAV; Blessing, 1995)
h = 55
Tmin = 0.067, Tmax = 0.636k = 1616
7322 measured reflectionsl = 1719
Refinement top
Refinement on F2Hydrogen site location: difmap (O-H) and geom (C-H)
Least-squares matrix: fullH atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.038 w = 1/[σ2(Fo2) + (0.0143P)2]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.056(Δ/σ)max < 0.001
S = 1.00Δρmax = 0.73 e Å3
1820 reflectionsΔρmin = 0.63 e Å3
107 parametersExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
0 restraintsExtinction coefficient: 0.0021 (3)
Primary atom site location: structure-invariant direct methodsAbsolute structure: Flack H D (1983), 727 Friedel pairs
Secondary atom site location: difference Fourier mapAbsolute structure parameter: 0.04 (3)
Special details top

Experimental. Melting points were determined on a Gallenkamp melting point apparatus and are uncorrected. IR measurements were recorded on a ATI Mattson Genesis FTIR spectrometer. 250 MHz 1H and 62.5 MHz 13C NMR spectra were determined on a Bruker 250 MHz s pectrometer. TLC chromatography plates were aluminium backed with a coating of Merck 60 F254 silica.

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
C10.7209 (15)0.0499 (4)0.4241 (4)0.0172 (14)
C20.6566 (14)0.0039 (4)0.3483 (4)0.0167 (15)
C30.4764 (15)0.0959 (4)0.3527 (4)0.0172 (15)
C40.3643 (14)0.1321 (5)0.4326 (4)0.0192 (14)
H40.24280.19490.43570.023*
C50.4303 (15)0.0766 (4)0.5075 (4)0.0148 (14)
C60.6087 (15)0.0159 (4)0.5058 (4)0.0176 (14)
O10.7570 (11)0.0285 (3)0.2683 (3)0.0237 (11)
H10.849 (14)0.085 (4)0.270 (4)0.028*
O20.6795 (11)0.0752 (3)0.5767 (3)0.0219 (12)
H20.634 (16)0.043 (5)0.617 (4)0.026*
Br10.95355 (16)0.17647 (5)0.41737 (4)0.02168 (17)
Br20.38328 (13)0.17109 (5)0.24986 (4)0.02274 (18)
Br30.26244 (16)0.12500 (5)0.61575 (4)0.02241 (18)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.022 (3)0.012 (3)0.018 (4)0.004 (3)0.003 (3)0.003 (3)
C20.017 (4)0.021 (3)0.013 (4)0.008 (3)0.002 (3)0.003 (3)
C30.019 (3)0.017 (3)0.015 (4)0.001 (3)0.006 (3)0.003 (3)
C40.021 (4)0.015 (3)0.022 (4)0.001 (3)0.006 (3)0.001 (3)
C50.017 (3)0.019 (3)0.008 (3)0.002 (3)0.003 (3)0.002 (3)
C60.024 (3)0.016 (3)0.013 (4)0.006 (3)0.006 (3)0.005 (3)
O10.033 (2)0.020 (2)0.018 (3)0.004 (2)0.005 (2)0.003 (2)
O20.031 (3)0.020 (2)0.015 (3)0.000 (2)0.001 (2)0.0017 (19)
Br10.0239 (3)0.0182 (3)0.0230 (4)0.0023 (3)0.0018 (3)0.0014 (3)
Br20.0281 (3)0.0229 (3)0.0173 (4)0.0016 (3)0.0019 (3)0.0025 (3)
Br30.0245 (3)0.0252 (3)0.0175 (3)0.0024 (3)0.0016 (3)0.0007 (3)
Geometric parameters (Å, º) top
C1—C21.376 (8)C4—C51.377 (8)
C1—C61.401 (8)C4—H40.9500
C1—Br11.890 (5)C5—C61.397 (8)
C2—O11.358 (7)C5—Br31.898 (6)
C2—C31.396 (7)C6—O21.358 (7)
C3—C41.387 (8)O1—H10.82 (5)
C3—Br21.886 (6)O2—H20.77 (6)
C2—C1—C6122.1 (5)C5—C4—H4120.2
C2—C1—Br1119.0 (5)C3—C4—H4120.2
C6—C1—Br1118.9 (4)C4—C5—C6121.9 (5)
O1—C2—C1123.2 (5)C4—C5—Br3118.9 (5)
O1—C2—C3117.7 (5)C6—C5—Br3119.1 (4)
C1—C2—C3119.2 (5)O2—C6—C5125.1 (5)
C4—C3—C2120.2 (5)O2—C6—C1117.9 (5)
C4—C3—Br2119.7 (4)C5—C6—C1117.1 (5)
C2—C3—Br2120.1 (5)C2—O1—H1112 (5)
C5—C4—C3119.6 (5)C6—O2—H2107 (5)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···Br10.82 (5)2.57 (6)3.078 (4)121 (5)
O1—H1···Br3i0.82 (5)2.90 (6)3.298 (4)112 (5)
O2—H2···O1ii0.77 (6)2.52 (6)3.229 (6)153 (6)
O2—H2···Br30.77 (6)2.64 (6)3.148 (4)125 (6)
Symmetry codes: (i) x+3/2, y, z1/2; (ii) x+3/2, y, z+1/2.
 

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