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The title compound, C7H5BrO3, crystallizes with two independent mol­ecules in the asymmetric unit. All the O atoms in the two mol­ecules contribute to the formation of a three-dimensional hydrogen-bonded network.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804016411/su6123sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804016411/su6123Isup2.hkl
Contains datablock I

CCDC reference: 248775

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.008 Å
  • R factor = 0.048
  • wR factor = 0.111
  • Data-to-parameter ratio = 14.5

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.98 PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 8
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 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 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 0 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SMART; data reduction: SAINT (Siemens, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL.

(I) top
Crystal data top
C7H5BrO3Z = 4
Mr = 217.02F(000) = 424
Triclinic, P1Dx = 1.904 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 4.805 (1) ÅCell parameters from 2884 reflections
b = 12.047 (2) Åθ = 6–27.5°
c = 14.666 (3) ŵ = 5.38 mm1
α = 114.06 (3)°T = 293 K
β = 90.40 (3)°Needle, colorless
γ = 101.19 (3)°0.14 × 0.06 × 0.05 mm
V = 756.9 (3) Å3
Data collection top
Bruker SMART CCD area-detector
diffractometer
2884 independent reflections
Radiation source: fine-focus sealed tube1786 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.036
φ and ω scansθmax = 26.0°, θmin = 1.5°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 55
Tmin = 0.514, Tmax = 0.767k = 1414
5095 measured reflectionsl = 1818
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)] = 0.048Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.111H-atom parameters constrained
S = 0.95 w = 1/[σ2(Fo2) + (0.0474P)2]
where P = (Fo2 + 2Fc2)/3
2884 reflections(Δ/σ)max = 0.003
199 parametersΔρmax = 0.52 e Å3
0 restraintsΔρmin = 0.29 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
Br10.25119 (15)0.48915 (6)1.17770 (5)0.0856 (3)
Br21.18701 (11)0.81837 (5)0.36237 (4)0.0617 (2)
C10.5842 (9)0.1934 (5)0.9862 (4)0.0453 (12)
C20.4840 (10)0.1796 (5)0.8913 (4)0.0517 (13)
C30.3207 (11)0.2593 (5)0.8842 (4)0.0569 (14)
H3A0.25260.24950.81910.080*
C40.2555 (12)0.3509 (5)0.9682 (5)0.0631 (15)
H4A0.14270.40590.96270.080*
C50.3520 (11)0.3630 (5)1.0618 (4)0.0539 (13)
C60.5135 (10)0.2875 (5)1.0717 (4)0.0520 (13)
H6A0.58010.29821.13720.080*
C70.7631 (10)0.1111 (5)0.9956 (4)0.0527 (13)
C80.6147 (9)0.7144 (4)0.5390 (4)0.0425 (12)
C90.7277 (11)0.7988 (5)0.6366 (4)0.0478 (12)
C100.9752 (11)0.8867 (5)0.6504 (4)0.0543 (14)
H10A1.05270.94490.71710.080*
C111.1106 (11)0.8911 (5)0.5699 (4)0.0523 (13)
H11A1.28390.95170.58000.080*
C120.9997 (10)0.8090 (5)0.4732 (4)0.0458 (12)
C130.7562 (10)0.7204 (4)0.4573 (4)0.0429 (12)
H13A0.68140.66270.39010.080*
C140.3498 (10)0.6208 (4)0.5223 (4)0.0415 (11)
O10.8472 (8)0.1329 (3)1.0875 (3)0.0646 (10)
H1A0.94950.08201.08570.080*
O20.8317 (8)0.0295 (4)0.9219 (3)0.0626 (10)
O30.5389 (8)0.0905 (4)0.8053 (3)0.0647 (10)
H3B0.64310.04850.81870.080*
O40.2719 (7)0.5438 (3)0.4282 (2)0.0548 (9)
H4B0.11530.49420.42440.080*
O50.2157 (7)0.6147 (3)0.5919 (3)0.0535 (9)
O60.6054 (8)0.8009 (3)0.7193 (3)0.0674 (11)
H6C0.45360.74460.70260.080*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.0976 (5)0.0739 (5)0.0734 (5)0.0245 (4)0.0197 (4)0.0159 (4)
Br20.0565 (4)0.0695 (4)0.0670 (4)0.0087 (3)0.0087 (3)0.0383 (3)
C10.039 (3)0.051 (3)0.044 (3)0.001 (2)0.003 (2)0.023 (3)
C20.043 (3)0.052 (3)0.051 (3)0.002 (3)0.001 (2)0.019 (3)
C30.059 (3)0.057 (4)0.054 (4)0.006 (3)0.006 (3)0.026 (3)
C40.065 (4)0.058 (4)0.072 (4)0.011 (3)0.002 (3)0.035 (3)
C50.052 (3)0.050 (3)0.059 (4)0.005 (3)0.005 (3)0.025 (3)
C60.052 (3)0.058 (4)0.049 (3)0.003 (3)0.002 (3)0.029 (3)
C70.039 (3)0.060 (4)0.056 (4)0.007 (3)0.001 (3)0.029 (3)
C80.038 (3)0.038 (3)0.052 (3)0.012 (2)0.001 (2)0.017 (3)
C90.050 (3)0.043 (3)0.045 (3)0.008 (3)0.001 (2)0.013 (3)
C100.050 (3)0.048 (3)0.051 (3)0.002 (3)0.003 (3)0.010 (3)
C110.047 (3)0.039 (3)0.064 (4)0.001 (2)0.004 (3)0.018 (3)
C120.043 (3)0.047 (3)0.052 (3)0.012 (2)0.003 (2)0.023 (3)
C130.044 (3)0.037 (3)0.043 (3)0.011 (2)0.002 (2)0.011 (2)
C140.042 (3)0.038 (3)0.043 (3)0.011 (2)0.004 (2)0.015 (3)
O10.074 (3)0.075 (3)0.055 (2)0.026 (2)0.0056 (19)0.033 (2)
O20.067 (2)0.062 (3)0.053 (2)0.015 (2)0.0026 (19)0.019 (2)
O30.069 (2)0.070 (3)0.048 (2)0.021 (2)0.0042 (18)0.015 (2)
O40.049 (2)0.053 (2)0.048 (2)0.0019 (17)0.0023 (16)0.0119 (19)
O50.054 (2)0.051 (2)0.047 (2)0.0015 (17)0.0045 (17)0.0165 (18)
O60.063 (2)0.073 (3)0.047 (2)0.005 (2)0.0054 (18)0.013 (2)
Geometric parameters (Å, º) top
Br1—C51.904 (5)C8—C131.403 (6)
Br2—C121.897 (5)C8—C141.471 (6)
C1—C61.403 (7)C9—O61.345 (6)
C1—C21.404 (7)C9—C101.381 (7)
C1—C71.476 (7)C10—C111.367 (7)
C2—O31.350 (6)C10—H10A0.9600
C2—C31.386 (7)C11—C121.384 (7)
C3—C41.366 (7)C11—H11A0.9600
C3—H3A0.9601C12—C131.368 (7)
C4—C51.387 (7)C13—H13A0.9600
C4—H4A0.9602C14—O51.231 (5)
C5—C61.353 (7)C14—O41.312 (5)
C6—H6A0.9601O1—H1A0.8499
C7—O21.227 (6)O3—H3B0.8500
C7—O11.309 (6)O4—H4B0.8500
C8—C91.402 (6)O6—H6C0.8500
C6—C1—C2118.7 (5)C13—C8—C14120.3 (4)
C6—C1—C7120.9 (5)O6—C9—C10117.1 (4)
C2—C1—C7120.5 (5)O6—C9—C8123.5 (5)
O3—C2—C3118.0 (5)C10—C9—C8119.4 (5)
O3—C2—C1122.5 (5)C11—C10—C9120.5 (5)
C3—C2—C1119.5 (5)C11—C10—H10A119.8
C4—C3—C2121.0 (5)C9—C10—H10A119.7
C4—C3—H3A119.8C10—C11—C12120.5 (5)
C2—C3—H3A119.2C10—C11—H11A120.1
C3—C4—C5119.2 (5)C12—C11—H11A119.3
C3—C4—H4A120.5C13—C12—C11120.3 (5)
C5—C4—H4A120.2C13—C12—Br2119.8 (4)
C6—C5—C4121.4 (5)C11—C12—Br2119.9 (4)
C6—C5—Br1120.2 (4)C12—C13—C8119.9 (4)
C4—C5—Br1118.4 (4)C12—C13—H13A120.0
C5—C6—C1120.1 (5)C8—C13—H13A120.0
C5—C6—H6A120.0O5—C14—O4123.0 (4)
C1—C6—H6A119.8O5—C14—C8122.2 (5)
O2—C7—O1122.6 (5)O4—C14—C8114.8 (4)
O2—C7—C1122.0 (5)C7—O1—H1A108.8
O1—C7—C1115.3 (5)C2—O3—H3B109.7
C9—C8—C13119.3 (5)C14—O4—H4B109.4
C9—C8—C14120.4 (5)C9—O6—H6C109.6
C6—C1—C2—O3179.1 (4)C13—C8—C9—O6179.3 (4)
C7—C1—C2—O31.6 (7)C14—C8—C9—O60.4 (7)
C6—C1—C2—C30.5 (7)C13—C8—C9—C100.3 (7)
C7—C1—C2—C3178.8 (4)C14—C8—C9—C10179.4 (4)
O3—C2—C3—C4179.5 (5)O6—C9—C10—C11179.4 (5)
C1—C2—C3—C40.1 (8)C8—C9—C10—C110.4 (8)
C2—C3—C4—C50.7 (8)C9—C10—C11—C121.0 (8)
C3—C4—C5—C61.2 (8)C10—C11—C12—C131.5 (8)
C3—C4—C5—Br1178.7 (4)C10—C11—C12—Br2178.9 (4)
C4—C5—C6—C10.8 (8)C11—C12—C13—C81.4 (7)
Br1—C5—C6—C1179.1 (3)Br2—C12—C13—C8179.0 (3)
C2—C1—C6—C50.1 (7)C9—C8—C13—C120.8 (7)
C7—C1—C6—C5179.3 (4)C14—C8—C13—C12178.9 (4)
C6—C1—C7—O2178.8 (5)C9—C8—C14—O51.6 (7)
C2—C1—C7—O20.5 (7)C13—C8—C14—O5178.1 (4)
C6—C1—C7—O10.0 (7)C9—C8—C14—O4177.2 (4)
C2—C1—C7—O1179.3 (4)C13—C8—C14—O43.1 (6)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1A···O2i0.851.832.681 (5)179
O3—H3B···O20.851.872.614 (5)145
O4—H4B···O5ii0.851.802.648 (5)177
O6—H6C···O50.851.902.633 (5)144
Symmetry codes: (i) x+2, y, z+2; (ii) x, y+1, z+1.
 

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