The six-membered ring of the title compound, C
16H
23BrO
10, adopts a chair conformation. The molecules are interconnected by weak C—H
O hydrogen bonds into a three-dimensional network.
Supporting information
CCDC reference: 282337
Key indicators
- Single-crystal X-ray study
- T = 295 K
- Mean (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
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
C16H23BrO10 | F(000) = 468 |
Mr = 455.25 | Dx = 1.466 Mg m−3 |
Monoclinic, P21 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2yb | Cell parameters from 2233 reflections |
a = 9.4153 (12) Å | θ = 2.8–18.3° |
b = 9.8326 (14) Å | µ = 2.04 mm−1 |
c = 11.2069 (19) Å | T = 295 K |
β = 96.391 (12)° | Prismatic, colourless |
V = 1031.1 (3) Å3 | 0.45 × 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 tube | 3044 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.040 |
ω scans | θmax = 26.1°, θmin = 3.6° |
Absorption correction: analytical (Alcock, 1970) | h = −11→11 |
Tmin = 0.686, Tmax = 0.871 | k = −12→11 |
13961 measured reflections | l = −13→13 |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.047 | H-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 reflections | Δρmax = 0.39 e Å−3 |
249 parameters | Δρmin = −0.58 e Å−3 |
1 restraint | Absolute structure: Flack & Bernardinelli (2000), with how many Friedel pairs |
Primary atom site location: structure-invariant direct methods | Absolute 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 | x | y | z | Uiso*/Ueq | |
Br | 0.44532 (6) | 0.87439 (9) | 0.10552 (6) | 0.0997 (3) | |
O1 | 0.7903 (3) | 0.7113 (3) | 0.4259 (2) | 0.0461 (6) | |
O4 | 1.1191 (3) | 0.6509 (3) | 0.6177 (2) | 0.0455 (6) | |
O6 | 1.2101 (3) | 0.8151 (3) | 0.4228 (2) | 0.0407 (6) | |
O8 | 1.0379 (3) | 0.7442 (3) | 0.2001 (2) | 0.0473 (7) | |
O10 | 0.7438 (3) | 0.7440 (3) | 0.2230 (2) | 0.0483 (7) | |
C1 | 0.8439 (4) | 0.6935 (4) | 0.3131 (3) | 0.0428 (9) | |
H1 | 0.8612 | 0.5968 | 0.2993 | 0.051* | |
C2 | 0.9815 (4) | 0.7729 (4) | 0.3119 (3) | 0.0378 (8) | |
H2 | 0.9637 | 0.8705 | 0.3195 | 0.045* | |
C3 | 1.0884 (4) | 0.7245 (4) | 0.4132 (3) | 0.0382 (8) | |
H3 | 1.1198 | 0.6324 | 0.3955 | 0.046* | |
C5 | 0.8828 (4) | 0.6483 (4) | 0.5194 (3) | 0.0420 (8) | |
H5 | 0.8994 | 0.5540 | 0.4963 | 0.050* | |
C4 | 1.0243 (4) | 0.7236 (4) | 0.5307 (3) | 0.0390 (8) | |
H4 | 1.0113 | 0.8169 | 0.5580 | 0.047* | |
C15 | 0.6246 (5) | 0.6522 (6) | 0.1936 (4) | 0.0580 (11) | |
H15A | 0.5650 | 0.6497 | 0.2588 | 0.070* | |
H15B | 0.6593 | 0.5610 | 0.1812 | 0.070* | |
C6 | 0.8085 (5) | 0.6476 (5) | 0.6302 (4) | 0.0535 (10) | |
H6A | 0.7121 | 0.6128 | 0.6119 | 0.064* | |
H6B | 0.8592 | 0.5889 | 0.6902 | 0.064* | |
C7 | 0.7320 (5) | 0.8035 (6) | 0.7730 (4) | 0.0601 (12) | |
O7 | 1.3641 (3) | 0.6423 (4) | 0.4314 (4) | 0.0809 (11) | |
C13 | 1.0254 (5) | 0.8379 (5) | 0.1129 (4) | 0.0528 (11) | |
C12 | 1.4549 (4) | 0.8683 (7) | 0.4627 (5) | 0.0712 (13) | |
H12C | 1.5477 | 0.8270 | 0.4768 | 0.107* | |
H12B | 1.4361 | 0.9191 | 0.5324 | 0.107* | |
H12A | 1.4523 | 0.9283 | 0.3949 | 0.107* | |
C9 | 1.2020 (5) | 0.7217 (5) | 0.7020 (4) | 0.0550 (10) | |
O5 | 1.1933 (5) | 0.8428 (4) | 0.7112 (4) | 0.0947 (14) | |
C16 | 0.5404 (5) | 0.7028 (6) | 0.0816 (4) | 0.0676 (13) | |
H16A | 0.4692 | 0.6353 | 0.0535 | 0.081* | |
H16B | 0.6038 | 0.7143 | 0.0198 | 0.081* | |
O9 | 0.9856 (5) | 0.9510 (4) | 0.1280 (3) | 0.0803 (11) | |
O2 | 0.8040 (3) | 0.7848 (3) | 0.6761 (2) | 0.0544 (7) | |
C11 | 1.3429 (4) | 0.7591 (5) | 0.4376 (4) | 0.0490 (10) | |
C10 | 1.3017 (5) | 0.6327 (7) | 0.7772 (4) | 0.0733 (14) | |
H10A | 1.3574 | 0.5807 | 0.7268 | 0.110* | |
H10B | 1.2484 | 0.5721 | 0.8226 | 0.110* | |
H10C | 1.3642 | 0.6873 | 0.8312 | 0.110* | |
C14 | 1.0672 (6) | 0.7818 (7) | −0.0004 (4) | 0.0768 (15) | |
H14A | 0.9949 | 0.7199 | −0.0344 | 0.115* | |
H14B | 1.1564 | 0.7344 | 0.0155 | 0.115* | |
H14C | 1.0774 | 0.8546 | −0.0558 | 0.115* | |
O3 | 0.6779 (6) | 0.7089 (6) | 0.8173 (4) | 0.1114 (18) | |
C8 | 0.7405 (9) | 0.9464 (7) | 0.8188 (6) | 0.094 (2) | |
H8A | 0.6789 | 1.0035 | 0.7663 | 0.141* | |
H8B | 0.8371 | 0.9784 | 0.8215 | 0.141* | |
H8C | 0.7109 | 0.9491 | 0.8981 | 0.141* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Br | 0.0768 (4) | 0.0924 (5) | 0.1193 (5) | −0.0015 (3) | −0.0365 (3) | 0.0122 (4) |
O1 | 0.0330 (12) | 0.0562 (17) | 0.0490 (14) | 0.0002 (12) | 0.0032 (10) | 0.0013 (13) |
O4 | 0.0478 (14) | 0.0390 (15) | 0.0474 (13) | 0.0043 (12) | −0.0056 (11) | 0.0036 (12) |
O6 | 0.0302 (12) | 0.0378 (14) | 0.0534 (13) | 0.0016 (10) | 0.0011 (10) | 0.0015 (11) |
O8 | 0.0477 (14) | 0.0526 (18) | 0.0417 (13) | 0.0073 (12) | 0.0057 (11) | −0.0015 (13) |
O10 | 0.0369 (12) | 0.0529 (18) | 0.0521 (14) | −0.0066 (12) | −0.0082 (10) | 0.0030 (13) |
C1 | 0.0411 (19) | 0.043 (2) | 0.0432 (19) | −0.0016 (16) | 0.0000 (15) | 0.0006 (16) |
C2 | 0.0361 (16) | 0.041 (2) | 0.0370 (16) | 0.0001 (15) | 0.0066 (13) | −0.0016 (16) |
C3 | 0.0368 (16) | 0.033 (2) | 0.0447 (18) | 0.0015 (15) | 0.0042 (14) | −0.0051 (16) |
C5 | 0.0430 (18) | 0.034 (2) | 0.0487 (18) | 0.0003 (16) | 0.0020 (15) | 0.0066 (17) |
C4 | 0.0394 (17) | 0.034 (2) | 0.0425 (18) | 0.0033 (15) | 0.0006 (14) | 0.0006 (16) |
C15 | 0.046 (2) | 0.066 (3) | 0.059 (2) | −0.017 (2) | −0.0037 (18) | 0.000 (2) |
C6 | 0.059 (2) | 0.051 (3) | 0.052 (2) | −0.005 (2) | 0.0140 (18) | 0.002 (2) |
C7 | 0.057 (2) | 0.073 (3) | 0.052 (2) | 0.005 (2) | 0.013 (2) | 0.009 (2) |
O7 | 0.0457 (17) | 0.058 (2) | 0.139 (3) | 0.0170 (16) | 0.0129 (19) | −0.001 (2) |
C13 | 0.048 (2) | 0.061 (3) | 0.048 (2) | −0.0013 (19) | 0.0007 (17) | 0.003 (2) |
C12 | 0.0366 (18) | 0.076 (3) | 0.099 (3) | −0.006 (3) | −0.0028 (19) | −0.003 (3) |
C9 | 0.061 (2) | 0.058 (3) | 0.044 (2) | −0.001 (2) | −0.0022 (18) | 0.001 (2) |
O5 | 0.131 (4) | 0.062 (3) | 0.079 (2) | −0.005 (2) | −0.041 (2) | −0.013 (2) |
C16 | 0.054 (2) | 0.091 (4) | 0.055 (2) | −0.018 (2) | −0.0069 (19) | 0.002 (2) |
O9 | 0.114 (3) | 0.066 (3) | 0.063 (2) | 0.002 (2) | 0.017 (2) | 0.0188 (19) |
O2 | 0.0599 (17) | 0.0510 (18) | 0.0568 (15) | 0.0041 (14) | 0.0256 (14) | 0.0043 (14) |
C11 | 0.0325 (18) | 0.055 (3) | 0.060 (2) | 0.0081 (18) | 0.0063 (16) | 0.002 (2) |
C10 | 0.059 (3) | 0.093 (4) | 0.063 (3) | 0.000 (3) | −0.016 (2) | 0.006 (3) |
C14 | 0.086 (3) | 0.102 (4) | 0.043 (2) | 0.001 (3) | 0.009 (2) | 0.000 (3) |
O3 | 0.140 (4) | 0.106 (4) | 0.103 (3) | −0.038 (3) | 0.077 (3) | −0.012 (3) |
C8 | 0.124 (5) | 0.083 (4) | 0.083 (4) | 0.034 (4) | 0.045 (4) | 0.005 (3) |
Geometric parameters (Å, º) top
Br—C16 | 1.943 (6) | C6—H6A | 0.9700 |
O1—C1 | 1.422 (5) | C6—H6B | 0.9700 |
O1—C5 | 1.427 (5) | C7—O3 | 1.194 (7) |
O4—C9 | 1.350 (5) | C7—O2 | 1.356 (5) |
O4—C4 | 1.436 (4) | C7—C8 | 1.495 (9) |
O6—C11 | 1.360 (5) | O7—C11 | 1.169 (6) |
O6—C3 | 1.446 (4) | C13—O9 | 1.191 (6) |
O8—C13 | 1.338 (5) | C13—C14 | 1.477 (7) |
O8—C2 | 1.443 (4) | C12—C11 | 1.510 (7) |
O10—C1 | 1.394 (5) | C12—H12C | 0.9600 |
O10—C15 | 1.449 (5) | C12—H12B | 0.9600 |
C1—C2 | 1.514 (5) | C12—H12A | 0.9600 |
C1—H1 | 0.9800 | C9—O5 | 1.199 (6) |
C2—C3 | 1.507 (5) | C9—C10 | 1.478 (7) |
C2—H2 | 0.9800 | C16—H16A | 0.9700 |
C3—C4 | 1.508 (5) | C16—H16B | 0.9700 |
C3—H3 | 0.9800 | C10—H10A | 0.9600 |
C5—C6 | 1.492 (5) | C10—H10B | 0.9600 |
C5—C4 | 1.517 (5) | C10—H10C | 0.9600 |
C5—H5 | 0.9800 | C14—H14A | 0.9600 |
C4—H4 | 0.9800 | C14—H14B | 0.9600 |
C15—C16 | 1.494 (7) | C14—H14C | 0.9600 |
C15—H15A | 0.9700 | C8—H8A | 0.9600 |
C15—H15B | 0.9700 | C8—H8B | 0.9600 |
C6—O2 | 1.446 (6) | C8—H8C | 0.9600 |
| | | |
C1—O1—C5 | 110.6 (3) | C5—C6—H6B | 109.9 |
C9—O4—C4 | 119.1 (3) | H6A—C6—H6B | 108.3 |
C11—O6—C3 | 118.0 (3) | O3—C7—O2 | 120.1 (5) |
C13—O8—C2 | 119.3 (3) | O3—C7—C8 | 126.8 (5) |
C1—O10—C15 | 112.8 (3) | O2—C7—C8 | 113.0 (4) |
O10—C1—O1 | 108.8 (3) | O9—C13—O8 | 122.9 (4) |
O10—C1—C2 | 108.7 (3) | O9—C13—C14 | 126.1 (5) |
O1—C1—C2 | 109.4 (3) | O8—C13—C14 | 111.1 (4) |
O10—C1—H1 | 110.0 | C11—C12—H12C | 109.5 |
O1—C1—H1 | 110.0 | C11—C12—H12B | 109.5 |
C2—C1—H1 | 110.0 | H12C—C12—H12B | 109.5 |
O8—C2—C3 | 108.3 (3) | C11—C12—H12A | 109.5 |
O8—C2—C1 | 107.8 (3) | H12C—C12—H12A | 109.5 |
C3—C2—C1 | 109.3 (3) | H12B—C12—H12A | 109.5 |
O8—C2—H2 | 110.5 | O5—C9—O4 | 122.2 (4) |
C3—C2—H2 | 110.5 | O5—C9—C10 | 125.8 (5) |
C1—C2—H2 | 110.5 | O4—C9—C10 | 112.0 (4) |
O6—C3—C2 | 108.6 (3) | C15—C16—Br | 112.5 (4) |
O6—C3—C4 | 109.2 (3) | C15—C16—H16A | 109.1 |
C2—C3—C4 | 111.2 (3) | Br—C16—H16A | 109.1 |
O6—C3—H3 | 109.3 | C15—C16—H16B | 109.1 |
C2—C3—H3 | 109.3 | Br—C16—H16B | 109.1 |
C4—C3—H3 | 109.3 | H16A—C16—H16B | 107.8 |
O1—C5—C6 | 108.0 (3) | C7—O2—C6 | 116.6 (4) |
O1—C5—C4 | 107.9 (3) | O7—C11—O6 | 123.5 (4) |
C6—C5—C4 | 114.9 (3) | O7—C11—C12 | 126.1 (4) |
O1—C5—H5 | 108.6 | O6—C11—C12 | 110.4 (4) |
C6—C5—H5 | 108.6 | C9—C10—H10A | 109.5 |
C4—C5—H5 | 108.6 | C9—C10—H10B | 109.5 |
O4—C4—C3 | 108.5 (3) | H10A—C10—H10B | 109.5 |
O4—C4—C5 | 106.7 (3) | C9—C10—H10C | 109.5 |
C3—C4—C5 | 111.3 (3) | H10A—C10—H10C | 109.5 |
O4—C4—H4 | 110.1 | H10B—C10—H10C | 109.5 |
C3—C4—H4 | 110.1 | C13—C14—H14A | 109.5 |
C5—C4—H4 | 110.1 | C13—C14—H14B | 109.5 |
O10—C15—C16 | 108.0 (4) | H14A—C14—H14B | 109.5 |
O10—C15—H15A | 110.1 | C13—C14—H14C | 109.5 |
C16—C15—H15A | 110.1 | H14A—C14—H14C | 109.5 |
O10—C15—H15B | 110.1 | H14B—C14—H14C | 109.5 |
C16—C15—H15B | 110.1 | C7—C8—H8A | 109.5 |
H15A—C15—H15B | 108.4 | C7—C8—H8B | 109.5 |
O2—C6—C5 | 109.1 (3) | H8A—C8—H8B | 109.5 |
O2—C6—H6A | 109.9 | C7—C8—H8C | 109.5 |
C5—C6—H6A | 109.9 | H8A—C8—H8C | 109.5 |
O2—C6—H6B | 109.9 | H8B—C8—H8C | 109.5 |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C1—H1···O5i | 0.98 | 2.55 | 3.479 (6) | 157 |
C6—H6B···O9i | 0.97 | 2.73 | 3.697 (6) | 173 |
C10—H10B···O9i | 0.96 | 2.63 | 3.497 (8) | 154 |
C8—H8A···O7ii | 0.96 | 2.60 | 3.459 (8) | 149 |
C12—H12C···O1iii | 0.96 | 2.66 | 3.581 (6) | 158 |
C16—H16B···O3iv | 0.97 | 2.45 | 3.367 (7) | 157 |
Symmetry codes: (i) −x+2, y−1/2, −z+1; (ii) −x+2, y+1/2, −z+1; (iii) x+1, y, z; (iv) x, y, z−1. |