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In the title compound, C16H23ClO10, 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

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806029242/kp2040sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806029242/kp2040Isup2.hkl
Contains datablock I

CCDC reference: 621395

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](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

Computing details top

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
C16H23ClO10F(000) = 432
Mr = 410.79Dx = 1.291 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
a = 10.554 (2) ÅCell parameters from 2515 reflections
b = 9.708 (2) Åθ = 2.9–23.7°
c = 10.599 (3) ŵ = 0.23 mm1
β = 103.299 (3)°T = 293 K
V = 1056.8 (4) Å3Block, colourless
Z = 20.44 × 0.28 × 0.19 mm
Data collection top
Siemens SMART 1000 CCD area-detector
diffractometer
3826 independent reflections
Radiation source: fine-focus sealed tube3238 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.015
Detector resolution: 8.33 pixels mm-1θmax = 26.1°, θmin = 2.0°
ω scansh = 137
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
k = 1111
Tmin = 0.907, Tmax = 0.958l = 1213
5996 measured reflections
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)] = 0.050H-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 reflectionsΔρmax = 0.24 e Å3
244 parametersΔρmin = 0.23 e Å3
1 restraintAbsolute structure: Flack (1983)
Primary atom site location: structure-invariant direct methodsAbsolute 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
xyzUiso*/Ueq
Cl10.89002 (14)0.90394 (14)0.94714 (16)0.1285 (5)
O10.70833 (16)0.78698 (19)1.27713 (17)0.0541 (4)
O20.9002 (2)0.7179 (4)1.5091 (2)0.1000 (9)
O30.9080 (5)0.6575 (7)1.7054 (4)0.192 (3)
O40.53350 (19)0.5680 (2)1.29663 (18)0.0634 (5)
O50.4092 (3)0.4689 (3)1.4127 (3)0.1026 (9)
O60.31615 (17)0.7485 (2)1.26063 (18)0.0639 (5)
O70.2828 (2)0.8094 (4)1.4538 (3)0.1085 (10)
O80.40841 (18)0.9640 (2)1.12690 (19)0.0626 (5)
O90.3064 (3)0.8437 (3)0.9542 (2)0.0921 (8)
O100.66859 (18)0.9294 (2)1.10408 (18)0.0652 (5)
C10.6280 (2)0.8946 (3)1.2145 (3)0.0534 (6)
H1A0.63600.97461.27220.064*
C20.4868 (2)0.8469 (3)1.1783 (3)0.0527 (6)
H2A0.47560.77251.11410.063*
C30.4468 (2)0.8000 (3)1.2989 (2)0.0551 (6)
H3A0.44730.87981.35560.066*
C40.5407 (3)0.6923 (3)1.3724 (2)0.0581 (7)
H4A0.51870.67181.45530.070*
C50.6780 (2)0.7478 (3)1.3964 (2)0.0578 (6)
H5A0.68410.82951.45180.069*
C60.7788 (3)0.6456 (4)1.4612 (3)0.0810 (9)
H6A0.75120.60131.53250.097*
H6B0.79000.57521.39980.097*
C70.9525 (4)0.7219 (4)1.6308 (3)0.0868 (10)
C81.0632 (4)0.8156 (6)1.6632 (4)0.1056 (13)
H8A1.09930.81341.75500.158*
H8B1.03500.90751.63750.158*
H8C1.12830.78761.61830.158*
C90.4661 (3)0.4626 (4)1.3279 (3)0.0726 (9)
C100.4715 (5)0.3392 (4)1.2456 (4)0.0998 (12)
H10A0.42230.26561.27170.150*
H10B0.56040.31081.25570.150*
H10C0.43520.36171.15640.150*
C110.2429 (3)0.7621 (4)1.3488 (3)0.0807 (10)
C120.1101 (4)0.7043 (7)1.2961 (5)0.123 (2)
H12A0.05860.71481.35920.185*
H12B0.11700.60841.27690.185*
H12C0.06950.75271.21830.185*
C130.3189 (3)0.9480 (3)1.0138 (3)0.0644 (7)
C140.2433 (4)1.0773 (4)0.9794 (5)0.0991 (13)
H14A0.17941.06430.89970.149*
H14B0.30111.15050.96900.149*
H14C0.20041.10051.04720.149*
C150.7839 (4)1.0146 (4)1.1337 (4)0.0854 (10)
H15A0.85310.96631.19330.102*
H15B0.76541.09891.17530.102*
C160.8259 (4)1.0480 (4)1.0158 (4)0.0938 (11)
H16A0.89201.11931.03510.113*
H16B0.75251.08480.95240.113*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.1351 (9)0.1031 (8)0.1770 (12)0.0114 (7)0.0971 (9)0.0063 (8)
O10.0501 (9)0.0579 (10)0.0582 (9)0.0038 (8)0.0204 (7)0.0001 (8)
O20.0601 (12)0.163 (3)0.0725 (13)0.0117 (15)0.0053 (10)0.0390 (17)
O30.218 (5)0.252 (6)0.090 (2)0.117 (5)0.005 (3)0.036 (3)
O40.0720 (12)0.0636 (12)0.0584 (10)0.0074 (10)0.0224 (9)0.0016 (9)
O50.1077 (19)0.108 (2)0.1021 (18)0.0235 (16)0.0442 (16)0.0265 (16)
O60.0485 (9)0.0852 (14)0.0618 (10)0.0037 (9)0.0207 (8)0.0089 (10)
O70.0867 (16)0.163 (3)0.0895 (16)0.0169 (18)0.0482 (14)0.0455 (19)
O80.0585 (11)0.0511 (10)0.0742 (12)0.0046 (8)0.0070 (9)0.0054 (9)
O90.1017 (17)0.0809 (17)0.0780 (14)0.0014 (14)0.0118 (13)0.0116 (13)
O100.0628 (11)0.0688 (13)0.0668 (11)0.0083 (10)0.0207 (9)0.0068 (10)
C10.0545 (14)0.0509 (13)0.0570 (14)0.0059 (11)0.0174 (11)0.0052 (12)
C20.0518 (13)0.0497 (14)0.0569 (13)0.0018 (11)0.0134 (10)0.0060 (12)
C30.0506 (13)0.0634 (16)0.0544 (13)0.0037 (12)0.0186 (11)0.0128 (12)
C40.0600 (15)0.0725 (17)0.0465 (12)0.0009 (13)0.0217 (11)0.0022 (13)
C50.0527 (14)0.0720 (17)0.0495 (12)0.0021 (13)0.0136 (10)0.0045 (13)
C60.0648 (18)0.099 (3)0.0758 (19)0.0042 (18)0.0089 (15)0.0209 (19)
C70.095 (2)0.094 (3)0.0687 (19)0.002 (2)0.0126 (18)0.018 (2)
C80.084 (2)0.122 (4)0.102 (3)0.005 (2)0.004 (2)0.010 (3)
C90.0658 (17)0.082 (2)0.0673 (17)0.0120 (16)0.0091 (15)0.0261 (17)
C100.120 (3)0.065 (2)0.110 (3)0.013 (2)0.017 (2)0.005 (2)
C110.0631 (17)0.109 (3)0.0791 (19)0.0080 (17)0.0339 (15)0.022 (2)
C120.073 (2)0.193 (6)0.118 (3)0.041 (3)0.053 (2)0.042 (4)
C130.0576 (15)0.0608 (18)0.0725 (17)0.0093 (13)0.0098 (13)0.0055 (16)
C140.084 (2)0.077 (2)0.121 (3)0.0096 (19)0.007 (2)0.022 (2)
C150.084 (2)0.083 (2)0.093 (2)0.0259 (19)0.0271 (18)0.004 (2)
C160.100 (3)0.079 (2)0.112 (3)0.014 (2)0.043 (2)0.011 (2)
Geometric parameters (Å, º) top
Cl1—C161.781 (4)C5—C61.501 (4)
O1—C11.412 (3)C5—H5A0.9800
O1—C51.425 (3)C6—H6A0.9700
O2—C71.282 (4)C6—H6B0.9700
O2—C61.447 (4)C7—C81.459 (6)
O3—C71.186 (5)C8—H8A0.9600
O4—C91.332 (4)C8—H8B0.9600
O4—C41.442 (4)C8—H8C0.9600
O5—C91.191 (4)C9—C101.491 (6)
O6—C111.349 (4)C10—H10A0.9600
O6—C31.435 (3)C10—H10B0.9600
O7—C111.188 (4)C10—H10C0.9600
O8—C131.354 (3)C11—C121.493 (5)
O8—C21.438 (3)C12—H12A0.9600
O9—C131.185 (4)C12—H12B0.9600
O10—C11.378 (3)C12—H12C0.9600
O10—C151.445 (4)C13—C141.487 (5)
C1—C21.523 (3)C14—H14A0.9600
C1—H1A0.9800C14—H14B0.9600
C2—C31.507 (4)C14—H14C0.9600
C2—H2A0.9800C15—C161.455 (5)
C3—C41.525 (4)C15—H15A0.9700
C3—H3A0.9800C15—H15B0.9700
C4—C51.512 (4)C16—H16A0.9700
C4—H4A0.9800C16—H16B0.9700
C1—O1—C5112.42 (19)C7—C8—H8A109.5
C7—O2—C6120.6 (3)C7—C8—H8B109.5
C9—O4—C4117.9 (2)H8A—C8—H8B109.5
C11—O6—C3115.9 (2)C7—C8—H8C109.5
C13—O8—C2117.9 (2)H8A—C8—H8C109.5
C1—O10—C15111.5 (2)H8B—C8—H8C109.5
O10—C1—O1108.1 (2)O5—C9—O4122.6 (4)
O10—C1—C2109.8 (2)O5—C9—C10125.2 (3)
O1—C1—C2109.9 (2)O4—C9—C10112.2 (3)
O10—C1—H1A109.7C9—C10—H10A109.5
O1—C1—H1A109.7C9—C10—H10B109.5
C2—C1—H1A109.7H10A—C10—H10B109.5
O8—C2—C3108.2 (2)C9—C10—H10C109.5
O8—C2—C1107.4 (2)H10A—C10—H10C109.5
C3—C2—C1109.1 (2)H10B—C10—H10C109.5
O8—C2—H2A110.7O7—C11—O6123.4 (3)
C3—C2—H2A110.7O7—C11—C12126.5 (3)
C1—C2—H2A110.7O6—C11—C12110.0 (3)
O6—C3—C2107.7 (2)C11—C12—H12A109.5
O6—C3—C4112.0 (2)C11—C12—H12B109.5
C2—C3—C4111.4 (2)H12A—C12—H12B109.5
O6—C3—H3A108.6C11—C12—H12C109.5
C2—C3—H3A108.6H12A—C12—H12C109.5
C4—C3—H3A108.6H12B—C12—H12C109.5
O4—C4—C5108.5 (2)O9—C13—O8122.7 (3)
O4—C4—C3110.2 (2)O9—C13—C14127.1 (3)
C5—C4—C3109.1 (2)O8—C13—C14110.2 (3)
O4—C4—H4A109.7C13—C14—H14A109.5
C5—C4—H4A109.7C13—C14—H14B109.5
C3—C4—H4A109.7H14A—C14—H14B109.5
O1—C5—C6107.6 (2)C13—C14—H14C109.5
O1—C5—C4110.4 (2)H14A—C14—H14C109.5
C6—C5—C4113.1 (3)H14B—C14—H14C109.5
O1—C5—H5A108.6O10—C15—C16110.4 (3)
C6—C5—H5A108.6O10—C15—H15A109.6
C4—C5—H5A108.6C16—C15—H15A109.6
O2—C6—C5108.5 (3)O10—C15—H15B109.6
O2—C6—H6A110.0C16—C15—H15B109.6
C5—C6—H6A110.0H15A—C15—H15B108.1
O2—C6—H6B110.0C15—C16—Cl1113.3 (3)
C5—C6—H6B110.0C15—C16—H16A108.9
H6A—C6—H6B108.4Cl1—C16—H16A108.9
O3—C7—O2120.7 (4)C15—C16—H16B108.9
O3—C7—C8126.2 (4)Cl1—C16—H16B108.9
O2—C7—C8113.0 (4)H16A—C16—H16B107.7
C15—O10—C1—O178.5 (3)C2—C3—C4—C553.1 (3)
C15—O10—C1—C2161.7 (3)C1—O1—C5—C6173.4 (2)
C5—O1—C1—O10177.2 (2)C1—O1—C5—C462.8 (3)
C5—O1—C1—C263.1 (3)O4—C4—C5—O164.2 (3)
C13—O8—C2—C3110.7 (3)C3—C4—C5—O155.9 (3)
C13—O8—C2—C1131.7 (2)O4—C4—C5—C656.4 (3)
O10—C1—C2—O866.9 (3)C3—C4—C5—C6176.5 (2)
O1—C1—C2—O8174.4 (2)C7—O2—C6—C5117.4 (4)
O10—C1—C2—C3176.1 (2)O1—C5—C6—O272.2 (3)
O1—C1—C2—C357.4 (3)C4—C5—C6—O2165.6 (2)
C11—O6—C3—C2150.1 (3)C6—O2—C7—O36.0 (8)
C11—O6—C3—C487.1 (3)C6—O2—C7—C8171.4 (4)
O8—C2—C3—O666.7 (3)C4—O4—C9—O52.3 (5)
C1—C2—C3—O6176.8 (2)C4—O4—C9—C10177.6 (3)
O8—C2—C3—C4170.1 (2)C3—O6—C11—O72.2 (6)
C1—C2—C3—C453.6 (3)C3—O6—C11—C12180.0 (4)
C9—O4—C4—C5138.7 (2)C2—O8—C13—O92.7 (4)
C9—O4—C4—C3101.9 (3)C2—O8—C13—C14177.2 (3)
O6—C3—C4—O454.7 (3)C1—O10—C15—C16179.1 (3)
C2—C3—C4—O466.0 (3)O10—C15—C16—Cl169.8 (4)
O6—C3—C4—C5173.7 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C2—H2A···O90.982.272.681 (4)104
C4—H4A···O50.982.282.662 (4)102
C5—H5A···O5i0.982.353.226 (4)149
C6—H6A···O30.972.242.636 (5)103
C12—H12A···O2ii0.962.563.510 (5)172
Symmetry codes: (i) x+1, y+1/2, z+3; (ii) x1, y, z.
 

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