In the title compound, C
16H
23ClO
10, the galactopyranoside ring adopts the
4C1 chair conformation with the acetyl group at C4 positioned axially and all other substituents equatorially. In the crystal structure, molecules are linked into chains along the
b axis by C—H
O interactions.
Supporting information
CCDC reference: 621395
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.005 Å
- R factor = 0.050
- wR factor = 0.141
- Data-to-parameter ratio = 15.7
checkCIF/PLATON results
No syntax errors found
Alert level B
PLAT220_ALERT_2_B Large Non-Solvent O Ueq(max)/Ueq(min) ... 3.55 Ratio
PLAT242_ALERT_2_B Check Low Ueq as Compared to Neighbors for C7
Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ?
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ?
PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for O2
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 C11
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C13
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 5
PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety C10
PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety C12
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 1
C16 H23 Cl O10
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 26.07
From the CIF: _reflns_number_total 3826
Count of symmetry unique reflns 2218
Completeness (_total/calc) 172.50%
TEST3: Check Friedels for noncentro structure
Estimate of Friedel pairs measured 1608
Fraction of Friedel pairs measured 0.725
Are heavy atom types Z>Si present yes
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C1 = . R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C2 = . R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C3 = . S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C4 = . S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C5 = . R
0 ALERT level A = In general: serious problem
2 ALERT level B = Potentially serious problem
10 ALERT level C = Check and explain
8 ALERT level G = General alerts; check
8 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
6 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
5 ALERT type 4 Improvement, methodology, query or suggestion
0 ALERT type 5 Informative message, check
Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; 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, PARST (Nardelli, 1995) and PLATON (Spek, 2003).
2,3,4,6-tetra-
O-acetyl-2-chloroethyl-
β-
D-galactopyranoside
top
Crystal data top
C16H23ClO10 | F(000) = 432 |
Mr = 410.79 | Dx = 1.291 Mg m−3 |
Monoclinic, P21 | Mo Kα radiation, λ = 0.71073 Å |
a = 10.554 (2) Å | Cell parameters from 2515 reflections |
b = 9.708 (2) Å | θ = 2.9–23.7° |
c = 10.599 (3) Å | µ = 0.23 mm−1 |
β = 103.299 (3)° | T = 293 K |
V = 1056.8 (4) Å3 | Block, colourless |
Z = 2 | 0.44 × 0.28 × 0.19 mm |
Data collection top
Siemens SMART 1000 CCD area-detector diffractometer | 3826 independent reflections |
Radiation source: fine-focus sealed tube | 3238 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.015 |
Detector resolution: 8.33 pixels mm-1 | θmax = 26.1°, θmin = 2.0° |
ω scans | h = −13→7 |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | k = −11→11 |
Tmin = 0.907, Tmax = 0.958 | l = −12→13 |
5996 measured reflections | |
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)] = 0.050 | H-atom parameters constrained |
wR(F2) = 0.141 | w = 1/[σ2(Fo2) + (0.0789P)2 + 0.1466P] where P = (Fo2 + 2Fc2)/3 |
S = 1.04 | (Δ/σ)max < 0.001 |
3826 reflections | Δρmax = 0.24 e Å−3 |
244 parameters | Δρmin = −0.23 e Å−3 |
1 restraint | Absolute structure: Flack (1983) |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.09 (11) |
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 | |
Cl1 | 0.89002 (14) | 0.90394 (14) | 0.94714 (16) | 0.1285 (5) | |
O1 | 0.70833 (16) | 0.78698 (19) | 1.27713 (17) | 0.0541 (4) | |
O2 | 0.9002 (2) | 0.7179 (4) | 1.5091 (2) | 0.1000 (9) | |
O3 | 0.9080 (5) | 0.6575 (7) | 1.7054 (4) | 0.192 (3) | |
O4 | 0.53350 (19) | 0.5680 (2) | 1.29663 (18) | 0.0634 (5) | |
O5 | 0.4092 (3) | 0.4689 (3) | 1.4127 (3) | 0.1026 (9) | |
O6 | 0.31615 (17) | 0.7485 (2) | 1.26063 (18) | 0.0639 (5) | |
O7 | 0.2828 (2) | 0.8094 (4) | 1.4538 (3) | 0.1085 (10) | |
O8 | 0.40841 (18) | 0.9640 (2) | 1.12690 (19) | 0.0626 (5) | |
O9 | 0.3064 (3) | 0.8437 (3) | 0.9542 (2) | 0.0921 (8) | |
O10 | 0.66859 (18) | 0.9294 (2) | 1.10408 (18) | 0.0652 (5) | |
C1 | 0.6280 (2) | 0.8946 (3) | 1.2145 (3) | 0.0534 (6) | |
H1A | 0.6360 | 0.9746 | 1.2722 | 0.064* | |
C2 | 0.4868 (2) | 0.8469 (3) | 1.1783 (3) | 0.0527 (6) | |
H2A | 0.4756 | 0.7725 | 1.1141 | 0.063* | |
C3 | 0.4468 (2) | 0.8000 (3) | 1.2989 (2) | 0.0551 (6) | |
H3A | 0.4473 | 0.8798 | 1.3556 | 0.066* | |
C4 | 0.5407 (3) | 0.6923 (3) | 1.3724 (2) | 0.0581 (7) | |
H4A | 0.5187 | 0.6718 | 1.4553 | 0.070* | |
C5 | 0.6780 (2) | 0.7478 (3) | 1.3964 (2) | 0.0578 (6) | |
H5A | 0.6841 | 0.8295 | 1.4518 | 0.069* | |
C6 | 0.7788 (3) | 0.6456 (4) | 1.4612 (3) | 0.0810 (9) | |
H6A | 0.7512 | 0.6013 | 1.5325 | 0.097* | |
H6B | 0.7900 | 0.5752 | 1.3998 | 0.097* | |
C7 | 0.9525 (4) | 0.7219 (4) | 1.6308 (3) | 0.0868 (10) | |
C8 | 1.0632 (4) | 0.8156 (6) | 1.6632 (4) | 0.1056 (13) | |
H8A | 1.0993 | 0.8134 | 1.7550 | 0.158* | |
H8B | 1.0350 | 0.9075 | 1.6375 | 0.158* | |
H8C | 1.1283 | 0.7876 | 1.6183 | 0.158* | |
C9 | 0.4661 (3) | 0.4626 (4) | 1.3279 (3) | 0.0726 (9) | |
C10 | 0.4715 (5) | 0.3392 (4) | 1.2456 (4) | 0.0998 (12) | |
H10A | 0.4223 | 0.2656 | 1.2717 | 0.150* | |
H10B | 0.5604 | 0.3108 | 1.2557 | 0.150* | |
H10C | 0.4352 | 0.3617 | 1.1564 | 0.150* | |
C11 | 0.2429 (3) | 0.7621 (4) | 1.3488 (3) | 0.0807 (10) | |
C12 | 0.1101 (4) | 0.7043 (7) | 1.2961 (5) | 0.123 (2) | |
H12A | 0.0586 | 0.7148 | 1.3592 | 0.185* | |
H12B | 0.1170 | 0.6084 | 1.2769 | 0.185* | |
H12C | 0.0695 | 0.7527 | 1.2183 | 0.185* | |
C13 | 0.3189 (3) | 0.9480 (3) | 1.0138 (3) | 0.0644 (7) | |
C14 | 0.2433 (4) | 1.0773 (4) | 0.9794 (5) | 0.0991 (13) | |
H14A | 0.1794 | 1.0643 | 0.8997 | 0.149* | |
H14B | 0.3011 | 1.1505 | 0.9690 | 0.149* | |
H14C | 0.2004 | 1.1005 | 1.0472 | 0.149* | |
C15 | 0.7839 (4) | 1.0146 (4) | 1.1337 (4) | 0.0854 (10) | |
H15A | 0.8531 | 0.9663 | 1.1933 | 0.102* | |
H15B | 0.7654 | 1.0989 | 1.1753 | 0.102* | |
C16 | 0.8259 (4) | 1.0480 (4) | 1.0158 (4) | 0.0938 (11) | |
H16A | 0.8920 | 1.1193 | 1.0351 | 0.113* | |
H16B | 0.7525 | 1.0848 | 0.9524 | 0.113* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cl1 | 0.1351 (9) | 0.1031 (8) | 0.1770 (12) | −0.0114 (7) | 0.0971 (9) | −0.0063 (8) |
O1 | 0.0501 (9) | 0.0579 (10) | 0.0582 (9) | 0.0038 (8) | 0.0204 (7) | −0.0001 (8) |
O2 | 0.0601 (12) | 0.163 (3) | 0.0725 (13) | −0.0117 (15) | 0.0053 (10) | 0.0390 (17) |
O3 | 0.218 (5) | 0.252 (6) | 0.090 (2) | −0.117 (5) | 0.005 (3) | 0.036 (3) |
O4 | 0.0720 (12) | 0.0636 (12) | 0.0584 (10) | −0.0074 (10) | 0.0224 (9) | 0.0016 (9) |
O5 | 0.1077 (19) | 0.108 (2) | 0.1021 (18) | −0.0235 (16) | 0.0442 (16) | 0.0265 (16) |
O6 | 0.0485 (9) | 0.0852 (14) | 0.0618 (10) | −0.0037 (9) | 0.0207 (8) | −0.0089 (10) |
O7 | 0.0867 (16) | 0.163 (3) | 0.0895 (16) | −0.0169 (18) | 0.0482 (14) | −0.0455 (19) |
O8 | 0.0585 (11) | 0.0511 (10) | 0.0742 (12) | 0.0046 (8) | 0.0070 (9) | −0.0054 (9) |
O9 | 0.1017 (17) | 0.0809 (17) | 0.0780 (14) | 0.0014 (14) | −0.0118 (13) | −0.0116 (13) |
O10 | 0.0628 (11) | 0.0688 (13) | 0.0668 (11) | −0.0083 (10) | 0.0207 (9) | 0.0068 (10) |
C1 | 0.0545 (14) | 0.0509 (13) | 0.0570 (14) | −0.0059 (11) | 0.0174 (11) | −0.0052 (12) |
C2 | 0.0518 (13) | 0.0497 (14) | 0.0569 (13) | 0.0018 (11) | 0.0134 (10) | −0.0060 (12) |
C3 | 0.0506 (13) | 0.0634 (16) | 0.0544 (13) | −0.0037 (12) | 0.0186 (11) | −0.0128 (12) |
C4 | 0.0600 (15) | 0.0725 (17) | 0.0465 (12) | −0.0009 (13) | 0.0217 (11) | 0.0022 (13) |
C5 | 0.0527 (14) | 0.0720 (17) | 0.0495 (12) | −0.0021 (13) | 0.0136 (10) | −0.0045 (13) |
C6 | 0.0648 (18) | 0.099 (3) | 0.0758 (19) | 0.0042 (18) | 0.0089 (15) | 0.0209 (19) |
C7 | 0.095 (2) | 0.094 (3) | 0.0687 (19) | −0.002 (2) | 0.0126 (18) | 0.018 (2) |
C8 | 0.084 (2) | 0.122 (4) | 0.102 (3) | −0.005 (2) | 0.004 (2) | 0.010 (3) |
C9 | 0.0658 (17) | 0.082 (2) | 0.0673 (17) | −0.0120 (16) | 0.0091 (15) | 0.0261 (17) |
C10 | 0.120 (3) | 0.065 (2) | 0.110 (3) | −0.013 (2) | 0.017 (2) | 0.005 (2) |
C11 | 0.0631 (17) | 0.109 (3) | 0.0791 (19) | −0.0080 (17) | 0.0339 (15) | −0.022 (2) |
C12 | 0.073 (2) | 0.193 (6) | 0.118 (3) | −0.041 (3) | 0.053 (2) | −0.042 (4) |
C13 | 0.0576 (15) | 0.0608 (18) | 0.0725 (17) | −0.0093 (13) | 0.0098 (13) | 0.0055 (16) |
C14 | 0.084 (2) | 0.077 (2) | 0.121 (3) | 0.0096 (19) | −0.007 (2) | 0.022 (2) |
C15 | 0.084 (2) | 0.083 (2) | 0.093 (2) | −0.0259 (19) | 0.0271 (18) | 0.004 (2) |
C16 | 0.100 (3) | 0.079 (2) | 0.112 (3) | −0.014 (2) | 0.043 (2) | 0.011 (2) |
Geometric parameters (Å, º) top
Cl1—C16 | 1.781 (4) | C5—C6 | 1.501 (4) |
O1—C1 | 1.412 (3) | C5—H5A | 0.9800 |
O1—C5 | 1.425 (3) | C6—H6A | 0.9700 |
O2—C7 | 1.282 (4) | C6—H6B | 0.9700 |
O2—C6 | 1.447 (4) | C7—C8 | 1.459 (6) |
O3—C7 | 1.186 (5) | C8—H8A | 0.9600 |
O4—C9 | 1.332 (4) | C8—H8B | 0.9600 |
O4—C4 | 1.442 (4) | C8—H8C | 0.9600 |
O5—C9 | 1.191 (4) | C9—C10 | 1.491 (6) |
O6—C11 | 1.349 (4) | C10—H10A | 0.9600 |
O6—C3 | 1.435 (3) | C10—H10B | 0.9600 |
O7—C11 | 1.188 (4) | C10—H10C | 0.9600 |
O8—C13 | 1.354 (3) | C11—C12 | 1.493 (5) |
O8—C2 | 1.438 (3) | C12—H12A | 0.9600 |
O9—C13 | 1.185 (4) | C12—H12B | 0.9600 |
O10—C1 | 1.378 (3) | C12—H12C | 0.9600 |
O10—C15 | 1.445 (4) | C13—C14 | 1.487 (5) |
C1—C2 | 1.523 (3) | C14—H14A | 0.9600 |
C1—H1A | 0.9800 | C14—H14B | 0.9600 |
C2—C3 | 1.507 (4) | C14—H14C | 0.9600 |
C2—H2A | 0.9800 | C15—C16 | 1.455 (5) |
C3—C4 | 1.525 (4) | C15—H15A | 0.9700 |
C3—H3A | 0.9800 | C15—H15B | 0.9700 |
C4—C5 | 1.512 (4) | C16—H16A | 0.9700 |
C4—H4A | 0.9800 | C16—H16B | 0.9700 |
| | | |
C1—O1—C5 | 112.42 (19) | C7—C8—H8A | 109.5 |
C7—O2—C6 | 120.6 (3) | C7—C8—H8B | 109.5 |
C9—O4—C4 | 117.9 (2) | H8A—C8—H8B | 109.5 |
C11—O6—C3 | 115.9 (2) | C7—C8—H8C | 109.5 |
C13—O8—C2 | 117.9 (2) | H8A—C8—H8C | 109.5 |
C1—O10—C15 | 111.5 (2) | H8B—C8—H8C | 109.5 |
O10—C1—O1 | 108.1 (2) | O5—C9—O4 | 122.6 (4) |
O10—C1—C2 | 109.8 (2) | O5—C9—C10 | 125.2 (3) |
O1—C1—C2 | 109.9 (2) | O4—C9—C10 | 112.2 (3) |
O10—C1—H1A | 109.7 | C9—C10—H10A | 109.5 |
O1—C1—H1A | 109.7 | C9—C10—H10B | 109.5 |
C2—C1—H1A | 109.7 | H10A—C10—H10B | 109.5 |
O8—C2—C3 | 108.2 (2) | C9—C10—H10C | 109.5 |
O8—C2—C1 | 107.4 (2) | H10A—C10—H10C | 109.5 |
C3—C2—C1 | 109.1 (2) | H10B—C10—H10C | 109.5 |
O8—C2—H2A | 110.7 | O7—C11—O6 | 123.4 (3) |
C3—C2—H2A | 110.7 | O7—C11—C12 | 126.5 (3) |
C1—C2—H2A | 110.7 | O6—C11—C12 | 110.0 (3) |
O6—C3—C2 | 107.7 (2) | C11—C12—H12A | 109.5 |
O6—C3—C4 | 112.0 (2) | C11—C12—H12B | 109.5 |
C2—C3—C4 | 111.4 (2) | H12A—C12—H12B | 109.5 |
O6—C3—H3A | 108.6 | C11—C12—H12C | 109.5 |
C2—C3—H3A | 108.6 | H12A—C12—H12C | 109.5 |
C4—C3—H3A | 108.6 | H12B—C12—H12C | 109.5 |
O4—C4—C5 | 108.5 (2) | O9—C13—O8 | 122.7 (3) |
O4—C4—C3 | 110.2 (2) | O9—C13—C14 | 127.1 (3) |
C5—C4—C3 | 109.1 (2) | O8—C13—C14 | 110.2 (3) |
O4—C4—H4A | 109.7 | C13—C14—H14A | 109.5 |
C5—C4—H4A | 109.7 | C13—C14—H14B | 109.5 |
C3—C4—H4A | 109.7 | H14A—C14—H14B | 109.5 |
O1—C5—C6 | 107.6 (2) | C13—C14—H14C | 109.5 |
O1—C5—C4 | 110.4 (2) | H14A—C14—H14C | 109.5 |
C6—C5—C4 | 113.1 (3) | H14B—C14—H14C | 109.5 |
O1—C5—H5A | 108.6 | O10—C15—C16 | 110.4 (3) |
C6—C5—H5A | 108.6 | O10—C15—H15A | 109.6 |
C4—C5—H5A | 108.6 | C16—C15—H15A | 109.6 |
O2—C6—C5 | 108.5 (3) | O10—C15—H15B | 109.6 |
O2—C6—H6A | 110.0 | C16—C15—H15B | 109.6 |
C5—C6—H6A | 110.0 | H15A—C15—H15B | 108.1 |
O2—C6—H6B | 110.0 | C15—C16—Cl1 | 113.3 (3) |
C5—C6—H6B | 110.0 | C15—C16—H16A | 108.9 |
H6A—C6—H6B | 108.4 | Cl1—C16—H16A | 108.9 |
O3—C7—O2 | 120.7 (4) | C15—C16—H16B | 108.9 |
O3—C7—C8 | 126.2 (4) | Cl1—C16—H16B | 108.9 |
O2—C7—C8 | 113.0 (4) | H16A—C16—H16B | 107.7 |
| | | |
C15—O10—C1—O1 | −78.5 (3) | C2—C3—C4—C5 | 53.1 (3) |
C15—O10—C1—C2 | 161.7 (3) | C1—O1—C5—C6 | −173.4 (2) |
C5—O1—C1—O10 | 177.2 (2) | C1—O1—C5—C4 | 62.8 (3) |
C5—O1—C1—C2 | −63.1 (3) | O4—C4—C5—O1 | 64.2 (3) |
C13—O8—C2—C3 | −110.7 (3) | C3—C4—C5—O1 | −55.9 (3) |
C13—O8—C2—C1 | 131.7 (2) | O4—C4—C5—C6 | −56.4 (3) |
O10—C1—C2—O8 | −66.9 (3) | C3—C4—C5—C6 | −176.5 (2) |
O1—C1—C2—O8 | 174.4 (2) | C7—O2—C6—C5 | 117.4 (4) |
O10—C1—C2—C3 | 176.1 (2) | O1—C5—C6—O2 | 72.2 (3) |
O1—C1—C2—C3 | 57.4 (3) | C4—C5—C6—O2 | −165.6 (2) |
C11—O6—C3—C2 | −150.1 (3) | C6—O2—C7—O3 | 6.0 (8) |
C11—O6—C3—C4 | 87.1 (3) | C6—O2—C7—C8 | −171.4 (4) |
O8—C2—C3—O6 | 66.7 (3) | C4—O4—C9—O5 | 2.3 (5) |
C1—C2—C3—O6 | −176.8 (2) | C4—O4—C9—C10 | −177.6 (3) |
O8—C2—C3—C4 | −170.1 (2) | C3—O6—C11—O7 | −2.2 (6) |
C1—C2—C3—C4 | −53.6 (3) | C3—O6—C11—C12 | −180.0 (4) |
C9—O4—C4—C5 | 138.7 (2) | C2—O8—C13—O9 | −2.7 (4) |
C9—O4—C4—C3 | −101.9 (3) | C2—O8—C13—C14 | 177.2 (3) |
O6—C3—C4—O4 | 54.7 (3) | C1—O10—C15—C16 | 179.1 (3) |
C2—C3—C4—O4 | −66.0 (3) | O10—C15—C16—Cl1 | −69.8 (4) |
O6—C3—C4—C5 | 173.7 (2) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C2—H2A···O9 | 0.98 | 2.27 | 2.681 (4) | 104 |
C4—H4A···O5 | 0.98 | 2.28 | 2.662 (4) | 102 |
C5—H5A···O5i | 0.98 | 2.35 | 3.226 (4) | 149 |
C6—H6A···O3 | 0.97 | 2.24 | 2.636 (5) | 103 |
C12—H12A···O2ii | 0.96 | 2.56 | 3.510 (5) | 172 |
Symmetry codes: (i) −x+1, y+1/2, −z+3; (ii) x−1, y, z. |