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The title compound, C8H12Br2O4, has crystallographic inversion symmetry. Mol­ecules adopt a pleated conformation, the OCH2-CH2CH2 torsion angles of the butane­diol residue being close to 60 and -60°. The mol­ecular packing is stabilized by a network of weak inter­molecular hydrogen bonds between the methyl­ene and the carbonyl groups of the bromo­acetate units. Each mol­ecule inter­acts with its four closest neighbours.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805007609/ac6162sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805007609/ac6162Isup2.hkl
Contains datablock I

CCDC reference: 270221

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.009 Å
  • R factor = 0.065
  • wR factor = 0.180
  • Data-to-parameter ratio = 25.1

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low .... 45 Perc. PLAT199_ALERT_1_C Check the Reported cell_measurement_temperature 293 PLAT200_ALERT_1_C Check the Reported cell_ambient_temperature .... 293 PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 9
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 4 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 2 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: CAD-4 Software (Kiers, 1994); cell refinement: CAD-4 Software; data reduction: local program; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97 and WinGX-PC (Version 1.64.05; Farrugia, 1999).

butane-1,4-diyl bis(bromoacetate) top
Crystal data top
C8H12Br2O4F(000) = 324
Mr = 331.98Dx = 1.902 Mg m3
Monoclinic, P21/cMelting point: 68 K
Hall symbol: -P 2ybcMo Kα radiation, λ = 0.71073 Å
a = 8.048 (3) ÅCell parameters from 25 reflections
b = 10.039 (2) Åθ = 12–21°
c = 7.298 (2) ŵ = 6.98 mm1
β = 100.58 (3)°T = 293 K
V = 579.6 (3) Å3Prism, colourless
Z = 20.52 × 0.17 × 0.13 mm
Data collection top
Enraf-Nonius CAD-4
diffractometer
764 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.086
Graphite monochromatorθmax = 30.0°, θmin = 2.6°
ω/2θ scansh = 110
Absorption correction: gaussian
(PLATON; Spek, 2003)
k = 140
Tmin = 0.302, Tmax = 0.463l = 1010
1784 measured reflections1 standard reflections every 120 min
1684 independent reflections intensity decay: none
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)] = 0.065Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.180Only H-atom displacement parameters refined
S = 1.01 w = 1/[σ2(Fo2) + (0.0813P)2 + 0.3508P]
where P = (Fo2 + 2Fc2)/3
1684 reflections(Δ/σ)max < 0.001
67 parametersΔρmax = 0.57 e Å3
0 restraintsΔρmin = 0.84 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.

Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane)

2.4152 (0.0306) x + 6.1541 (0.0295) y - 5.6452 (0.0158) z = 1.2376 (0.0361)

* -0.0047 (0.0015) C2 * 0.0169 (0.0053) C3 * -0.0070 (0.0022) O3 * -0.0053 (0.0017) O4

Rms deviation of fitted atoms = 0.0098

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
Br10.24280 (9)0.90348 (9)0.54678 (11)0.0742 (4)
O40.7021 (5)0.9159 (4)0.8666 (6)0.0445 (10)
O30.5924 (6)0.7638 (5)0.6542 (8)0.0728 (15)
C30.5779 (8)0.8588 (7)0.7474 (9)0.0478 (15)
C60.9865 (8)0.9290 (6)1.0295 (10)0.0511 (16)
H6A1.09460.88351.05480.057 (13)*
H6B0.94170.93051.14420.057 (13)*
C20.4162 (8)0.9308 (7)0.7605 (10)0.0591 (19)
H2A0.43931.02540.77490.10 (2)*
H2B0.37590.90040.87060.10 (2)*
C50.8676 (8)0.8524 (7)0.8846 (10)0.0542 (16)
H5A0.90640.85450.76640.072 (15)*
H5B0.86130.76020.92270.072 (15)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.0614 (5)0.0853 (7)0.0660 (5)0.0109 (4)0.0140 (3)0.0012 (4)
O40.038 (2)0.047 (2)0.048 (2)0.0002 (18)0.0074 (18)0.0080 (18)
O30.069 (3)0.066 (3)0.080 (3)0.000 (3)0.004 (3)0.038 (3)
C30.052 (4)0.045 (4)0.045 (3)0.007 (3)0.006 (3)0.004 (3)
C60.037 (3)0.051 (4)0.062 (4)0.006 (3)0.000 (3)0.006 (3)
C20.046 (4)0.074 (5)0.054 (4)0.001 (3)0.001 (3)0.018 (3)
C50.048 (4)0.050 (4)0.062 (4)0.006 (3)0.002 (3)0.006 (3)
Geometric parameters (Å, º) top
Br1—C21.912 (6)C6—H6A0.9700
O4—C31.329 (7)C6—H6B0.9700
O4—C51.461 (7)C2—H2A0.9700
O3—C31.190 (7)C2—H2B0.9700
C3—C21.507 (9)C5—H5A0.9700
C6—C51.501 (9)C5—H5B0.9700
C6—C6i1.517 (12)
C3—O4—C5115.7 (5)C3—C2—H2A109.0
O3—C3—O4125.4 (6)Br1—C2—H2A109.0
O3—C3—C2126.7 (6)C3—C2—H2B109.0
O4—C3—C2107.8 (5)Br1—C2—H2B109.0
C5—C6—C6i112.8 (7)H2A—C2—H2B107.8
C5—C6—H6A109.0O4—C5—C6107.0 (5)
C6i—C6—H6A109.0O4—C5—H5A110.3
C5—C6—H6B109.0C6—C5—H5A110.3
C6i—C6—H6B109.0O4—C5—H5B110.3
H6A—C6—H6B107.8C6—C5—H5B110.3
C3—C2—Br1112.9 (4)H5A—C5—H5B108.6
C5—O4—C3—O31.5 (9)O4—C3—C2—Br1160.3 (4)
C5—O4—C3—C2175.2 (5)C3—O4—C5—C6178.0 (5)
O3—C3—C2—Br123.0 (9)C6ii—C6—C5—O465.0 (9)
Symmetry codes: (i) x+2, y+2, z+2; (ii) x+1, y+1, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C2—H2A···O3iii0.972.473.403 (9)161
Symmetry code: (iii) x+1, y+1/2, z+3/2.
 

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