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The six-membered ring of the title compound, C16H23BrO10, adopts a chair conformation. The mol­ecules are interconnected by weak C—H...O hydrogen bonds into a three-dimensional network.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805022555/dn6234sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805022555/dn6234Isup2.hkl
Contains datablock I

CCDC reference: 282337

Key indicators

  • Single-crystal X-ray study
  • T = 295 K
  • Mean [sigma](C-C) = 0.006 Å
  • R factor = 0.047
  • wR factor = 0.142
  • Data-to-parameter ratio = 15.6

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT220_ALERT_2_C Large Non-Solvent O Ueq(max)/Ueq(min) ... 2.75 Ratio PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.13 Ratio PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C7 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C9 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C13 PLAT480_ALERT_4_C Long H...A H-Bond Reported H6B .. O9 .. 2.73 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H10B .. O9 .. 2.63 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H12C .. O1 .. 2.66 Ang. PLAT726_ALERT_1_C H...A Calc 2.61723, Rep 2.63000 Dev... 0.01 Ang. H10B -O9 1.555 2.746
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 26.06 From the CIF: _reflns_number_total 3873 Count of symmetry unique reflns 2162 Completeness (_total/calc) 179.14% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 1711 Fraction of Friedel pairs measured 0.791 Are heavy atom types Z>Si present yes
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 9 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 4 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 4 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2003); cell refinement: CrysAlis RED (Oxford Diffraction, 2003); data reduction: CrysAlis RED; 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.

2-Bromoethyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside top
Crystal data top
C16H23BrO10F(000) = 468
Mr = 455.25Dx = 1.466 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ybCell parameters from 2233 reflections
a = 9.4153 (12) Åθ = 2.8–18.3°
b = 9.8326 (14) ŵ = 2.04 mm1
c = 11.2069 (19) ÅT = 295 K
β = 96.391 (12)°Prismatic, colourless
V = 1031.1 (3) Å30.45 × 0.10 × 0.08 mm
Z = 2
Data collection top
Oxford Xcalibur 3 CCD area-detector
diffractometer
3873 independent reflections
Radiation source: fine-focus sealed tube3044 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.040
ω scansθmax = 26.1°, θmin = 3.6°
Absorption correction: analytical
(Alcock, 1970)
h = 1111
Tmin = 0.686, Tmax = 0.871k = 1211
13961 measured reflectionsl = 1313
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)] = 0.047H-atom parameters constrained
wR(F2) = 0.142 w = 1/[σ2(Fo2) + (0.0929P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max = 0.001
3873 reflectionsΔρmax = 0.39 e Å3
249 parametersΔρmin = 0.58 e Å3
1 restraintAbsolute structure: Flack & Bernardinelli (2000), with how many Friedel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.005 (13)
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
Br0.44532 (6)0.87439 (9)0.10552 (6)0.0997 (3)
O10.7903 (3)0.7113 (3)0.4259 (2)0.0461 (6)
O41.1191 (3)0.6509 (3)0.6177 (2)0.0455 (6)
O61.2101 (3)0.8151 (3)0.4228 (2)0.0407 (6)
O81.0379 (3)0.7442 (3)0.2001 (2)0.0473 (7)
O100.7438 (3)0.7440 (3)0.2230 (2)0.0483 (7)
C10.8439 (4)0.6935 (4)0.3131 (3)0.0428 (9)
H10.86120.59680.29930.051*
C20.9815 (4)0.7729 (4)0.3119 (3)0.0378 (8)
H20.96370.87050.31950.045*
C31.0884 (4)0.7245 (4)0.4132 (3)0.0382 (8)
H31.11980.63240.39550.046*
C50.8828 (4)0.6483 (4)0.5194 (3)0.0420 (8)
H50.89940.55400.49630.050*
C41.0243 (4)0.7236 (4)0.5307 (3)0.0390 (8)
H41.01130.81690.55800.047*
C150.6246 (5)0.6522 (6)0.1936 (4)0.0580 (11)
H15A0.56500.64970.25880.070*
H15B0.65930.56100.18120.070*
C60.8085 (5)0.6476 (5)0.6302 (4)0.0535 (10)
H6A0.71210.61280.61190.064*
H6B0.85920.58890.69020.064*
C70.7320 (5)0.8035 (6)0.7730 (4)0.0601 (12)
O71.3641 (3)0.6423 (4)0.4314 (4)0.0809 (11)
C131.0254 (5)0.8379 (5)0.1129 (4)0.0528 (11)
C121.4549 (4)0.8683 (7)0.4627 (5)0.0712 (13)
H12C1.54770.82700.47680.107*
H12B1.43610.91910.53240.107*
H12A1.45230.92830.39490.107*
C91.2020 (5)0.7217 (5)0.7020 (4)0.0550 (10)
O51.1933 (5)0.8428 (4)0.7112 (4)0.0947 (14)
C160.5404 (5)0.7028 (6)0.0816 (4)0.0676 (13)
H16A0.46920.63530.05350.081*
H16B0.60380.71430.01980.081*
O90.9856 (5)0.9510 (4)0.1280 (3)0.0803 (11)
O20.8040 (3)0.7848 (3)0.6761 (2)0.0544 (7)
C111.3429 (4)0.7591 (5)0.4376 (4)0.0490 (10)
C101.3017 (5)0.6327 (7)0.7772 (4)0.0733 (14)
H10A1.35740.58070.72680.110*
H10B1.24840.57210.82260.110*
H10C1.36420.68730.83120.110*
C141.0672 (6)0.7818 (7)0.0004 (4)0.0768 (15)
H14A0.99490.71990.03440.115*
H14B1.15640.73440.01550.115*
H14C1.07740.85460.05580.115*
O30.6779 (6)0.7089 (6)0.8173 (4)0.1114 (18)
C80.7405 (9)0.9464 (7)0.8188 (6)0.094 (2)
H8A0.67891.00350.76630.141*
H8B0.83710.97840.82150.141*
H8C0.71090.94910.89810.141*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br0.0768 (4)0.0924 (5)0.1193 (5)0.0015 (3)0.0365 (3)0.0122 (4)
O10.0330 (12)0.0562 (17)0.0490 (14)0.0002 (12)0.0032 (10)0.0013 (13)
O40.0478 (14)0.0390 (15)0.0474 (13)0.0043 (12)0.0056 (11)0.0036 (12)
O60.0302 (12)0.0378 (14)0.0534 (13)0.0016 (10)0.0011 (10)0.0015 (11)
O80.0477 (14)0.0526 (18)0.0417 (13)0.0073 (12)0.0057 (11)0.0015 (13)
O100.0369 (12)0.0529 (18)0.0521 (14)0.0066 (12)0.0082 (10)0.0030 (13)
C10.0411 (19)0.043 (2)0.0432 (19)0.0016 (16)0.0000 (15)0.0006 (16)
C20.0361 (16)0.041 (2)0.0370 (16)0.0001 (15)0.0066 (13)0.0016 (16)
C30.0368 (16)0.033 (2)0.0447 (18)0.0015 (15)0.0042 (14)0.0051 (16)
C50.0430 (18)0.034 (2)0.0487 (18)0.0003 (16)0.0020 (15)0.0066 (17)
C40.0394 (17)0.034 (2)0.0425 (18)0.0033 (15)0.0006 (14)0.0006 (16)
C150.046 (2)0.066 (3)0.059 (2)0.017 (2)0.0037 (18)0.000 (2)
C60.059 (2)0.051 (3)0.052 (2)0.005 (2)0.0140 (18)0.002 (2)
C70.057 (2)0.073 (3)0.052 (2)0.005 (2)0.013 (2)0.009 (2)
O70.0457 (17)0.058 (2)0.139 (3)0.0170 (16)0.0129 (19)0.001 (2)
C130.048 (2)0.061 (3)0.048 (2)0.0013 (19)0.0007 (17)0.003 (2)
C120.0366 (18)0.076 (3)0.099 (3)0.006 (3)0.0028 (19)0.003 (3)
C90.061 (2)0.058 (3)0.044 (2)0.001 (2)0.0022 (18)0.001 (2)
O50.131 (4)0.062 (3)0.079 (2)0.005 (2)0.041 (2)0.013 (2)
C160.054 (2)0.091 (4)0.055 (2)0.018 (2)0.0069 (19)0.002 (2)
O90.114 (3)0.066 (3)0.063 (2)0.002 (2)0.017 (2)0.0188 (19)
O20.0599 (17)0.0510 (18)0.0568 (15)0.0041 (14)0.0256 (14)0.0043 (14)
C110.0325 (18)0.055 (3)0.060 (2)0.0081 (18)0.0063 (16)0.002 (2)
C100.059 (3)0.093 (4)0.063 (3)0.000 (3)0.016 (2)0.006 (3)
C140.086 (3)0.102 (4)0.043 (2)0.001 (3)0.009 (2)0.000 (3)
O30.140 (4)0.106 (4)0.103 (3)0.038 (3)0.077 (3)0.012 (3)
C80.124 (5)0.083 (4)0.083 (4)0.034 (4)0.045 (4)0.005 (3)
Geometric parameters (Å, º) top
Br—C161.943 (6)C6—H6A0.9700
O1—C11.422 (5)C6—H6B0.9700
O1—C51.427 (5)C7—O31.194 (7)
O4—C91.350 (5)C7—O21.356 (5)
O4—C41.436 (4)C7—C81.495 (9)
O6—C111.360 (5)O7—C111.169 (6)
O6—C31.446 (4)C13—O91.191 (6)
O8—C131.338 (5)C13—C141.477 (7)
O8—C21.443 (4)C12—C111.510 (7)
O10—C11.394 (5)C12—H12C0.9600
O10—C151.449 (5)C12—H12B0.9600
C1—C21.514 (5)C12—H12A0.9600
C1—H10.9800C9—O51.199 (6)
C2—C31.507 (5)C9—C101.478 (7)
C2—H20.9800C16—H16A0.9700
C3—C41.508 (5)C16—H16B0.9700
C3—H30.9800C10—H10A0.9600
C5—C61.492 (5)C10—H10B0.9600
C5—C41.517 (5)C10—H10C0.9600
C5—H50.9800C14—H14A0.9600
C4—H40.9800C14—H14B0.9600
C15—C161.494 (7)C14—H14C0.9600
C15—H15A0.9700C8—H8A0.9600
C15—H15B0.9700C8—H8B0.9600
C6—O21.446 (6)C8—H8C0.9600
C1—O1—C5110.6 (3)C5—C6—H6B109.9
C9—O4—C4119.1 (3)H6A—C6—H6B108.3
C11—O6—C3118.0 (3)O3—C7—O2120.1 (5)
C13—O8—C2119.3 (3)O3—C7—C8126.8 (5)
C1—O10—C15112.8 (3)O2—C7—C8113.0 (4)
O10—C1—O1108.8 (3)O9—C13—O8122.9 (4)
O10—C1—C2108.7 (3)O9—C13—C14126.1 (5)
O1—C1—C2109.4 (3)O8—C13—C14111.1 (4)
O10—C1—H1110.0C11—C12—H12C109.5
O1—C1—H1110.0C11—C12—H12B109.5
C2—C1—H1110.0H12C—C12—H12B109.5
O8—C2—C3108.3 (3)C11—C12—H12A109.5
O8—C2—C1107.8 (3)H12C—C12—H12A109.5
C3—C2—C1109.3 (3)H12B—C12—H12A109.5
O8—C2—H2110.5O5—C9—O4122.2 (4)
C3—C2—H2110.5O5—C9—C10125.8 (5)
C1—C2—H2110.5O4—C9—C10112.0 (4)
O6—C3—C2108.6 (3)C15—C16—Br112.5 (4)
O6—C3—C4109.2 (3)C15—C16—H16A109.1
C2—C3—C4111.2 (3)Br—C16—H16A109.1
O6—C3—H3109.3C15—C16—H16B109.1
C2—C3—H3109.3Br—C16—H16B109.1
C4—C3—H3109.3H16A—C16—H16B107.8
O1—C5—C6108.0 (3)C7—O2—C6116.6 (4)
O1—C5—C4107.9 (3)O7—C11—O6123.5 (4)
C6—C5—C4114.9 (3)O7—C11—C12126.1 (4)
O1—C5—H5108.6O6—C11—C12110.4 (4)
C6—C5—H5108.6C9—C10—H10A109.5
C4—C5—H5108.6C9—C10—H10B109.5
O4—C4—C3108.5 (3)H10A—C10—H10B109.5
O4—C4—C5106.7 (3)C9—C10—H10C109.5
C3—C4—C5111.3 (3)H10A—C10—H10C109.5
O4—C4—H4110.1H10B—C10—H10C109.5
C3—C4—H4110.1C13—C14—H14A109.5
C5—C4—H4110.1C13—C14—H14B109.5
O10—C15—C16108.0 (4)H14A—C14—H14B109.5
O10—C15—H15A110.1C13—C14—H14C109.5
C16—C15—H15A110.1H14A—C14—H14C109.5
O10—C15—H15B110.1H14B—C14—H14C109.5
C16—C15—H15B110.1C7—C8—H8A109.5
H15A—C15—H15B108.4C7—C8—H8B109.5
O2—C6—C5109.1 (3)H8A—C8—H8B109.5
O2—C6—H6A109.9C7—C8—H8C109.5
C5—C6—H6A109.9H8A—C8—H8C109.5
O2—C6—H6B109.9H8B—C8—H8C109.5
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C1—H1···O5i0.982.553.479 (6)157
C6—H6B···O9i0.972.733.697 (6)173
C10—H10B···O9i0.962.633.497 (8)154
C8—H8A···O7ii0.962.603.459 (8)149
C12—H12C···O1iii0.962.663.581 (6)158
C16—H16B···O3iv0.972.453.367 (7)157
Symmetry codes: (i) x+2, y1/2, z+1; (ii) x+2, y+1/2, z+1; (iii) x+1, y, z; (iv) x, y, z1.
 

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