2-[(2-Chloro­ethoxy)eth­yl]-2,3,4,6-tetra-O-acetyl-β-d-glucopyran­oside

Zhang, X.-R.; Zhang, H.-Q.; Yang, X.-H.; Bi, S.

doi:10.1107/S1600536807028127

2-[(2-Chloroethoxy)ethyl]-2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside

X.-R. Zhang, H.-Q. Zhang, X.-H. Yang and S. Bi

In the title compound, C₁₈H₂₇ClO₁₁, the glucopyranoside ring adopts a chair conformation. All the substituents attached to the six-membered ring are in equatorial positions. In the crystal structure, molecules related by translation along the a axis are linked into chains by weak intermolecular C—H

O hydrogen bonds. The chloroethyl unit is disordered over two sites in a ratio of 0.7:0.3.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807028127/cv2250sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807028127/cv2250Isup2.hkl Contains datablock I

CCDC reference: 654926

checkCIF report

Key indicators

Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.005 Å
Disorder in main residue
R factor = 0.048
wR factor = 0.140
Data-to-parameter ratio = 14.2

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
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
PLAT301_ALERT_3_C Main Residue  Disorder .........................       9.00 Perc.
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         C8
PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety        C10
PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety        C12
PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety        C14
PLAT410_ALERT_2_C Short Intra H...H Contact  H16B   ..  H17C    ..       1.93 Ang.
PLAT410_ALERT_2_C Short Intra H...H Contact  H16B   ..  H17D    ..       1.91 Ang.
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      31.40 Deg.
              C17  -O11  -C17'    1.555   1.555   1.555

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           25.09
           From the CIF: _reflns_number_total               4018
           Count of symmetry unique reflns         2313
           Completeness (_total/calc)            173.71%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured      1705
           Fraction of Friedel pairs measured     0.737
           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     = .          R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C5     = .          R
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......          6

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
  13 ALERT level C = Check and explain
   9 ALERT level G = General alerts; check

   7 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
   3 ALERT type 3 Indicator that the structure quality may be low
   6 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Comment top

In the title compound, (I) (Fig. 1), all bond lengths and angles are within normal ranges. The galactopyranoside ring adopts a chair conformation. All the substituents attached to the six-membered ring are in equatorial positions, assumed to be the most stable of all possible conformations due to the relatively low energy. There exist five intramolecular hydrogen bonds, forming five closed five-membered rings which contribute to the planarity of the substituents. In the crystal, the molecules are linked into chains along the a axis by C15—H15B···O5 and C18—H18B···O9 intermolecular hydrogen bonds.

Related literature top

For the crystal structure of 2,3,4,6-tetra-O-acetyl-2-chloroethyl-β-D-galactopyranoside, see: Zhang et al. (2006).

Experimental top

Compound (I) was prepared according to the method of Zhang et al. (2006). Single crystals suitable for X-ray diffraction analysis were obtained by slow evaporation of an ethanol-water (3:1 v/v) solution over a period of 5 d.

Structure description top

For the crystal structure of 2,3,4,6-tetra-O-acetyl-2-chloroethyl-β-D-galactopyranoside, see: Zhang et al. (2006).

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SMART; data reduction: SAINT (Siemens, 1996); program(s) used to solve structure: SHELXTL (Sheldrick, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXTL and PARST95 (Nardelli, 1995).

Figures top

Fig. 1. The molecular structure of (I) showing 50% probability displacement ellipsoids and the atom numbering scheme.

2-[(2-Chloroethoxy)ethyl]-2,3,4,6-tetra-O-acetyl-β-D-galactopyranoside top

Crystal data top

C₁₈H₂₇ClO₁₁	D_x = 1.332 Mg m⁻³
M_r = 454.85	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P2₁2₁2₁	Cell parameters from 3522 reflections
a = 7.5382 (13) Å	θ = 2.4–21.1°
b = 14.195 (3) Å	µ = 0.22 mm⁻¹
c = 21.204 (4) Å	T = 293 K
V = 2269.0 (8) Å³	Column, colourless
Z = 4	0.50 × 0.22 × 0.16 mm
F(000) = 960

Data collection top

Bruker SMART CCD area-detector diffractometer	4018 independent reflections
Radiation source: fine-focus sealed tube	3116 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.024
φ and ω scans	θ_max = 25.1°, θ_min = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −8→8
T_min = 0.932, T_max = 0.956	k = −16→8
11900 measured reflections	l = −25→25

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)] = 0.048	H-atom parameters constrained
wR(F²) = 0.140	w = 1/[σ²(F_o²) + (0.0807P)² + 0.2077P] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max = 0.002
4018 reflections	Δρ_max = 0.24 e Å⁻³
282 parameters	Δρ_min = −0.14 e Å⁻³
6 restraints	Absolute structure: Flack (1983), 1705 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.04 (15)

Crystal data top

C₁₈H₂₇ClO₁₁	V = 2269.0 (8) Å³
M_r = 454.85	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 7.5382 (13) Å	µ = 0.22 mm⁻¹
b = 14.195 (3) Å	T = 293 K
c = 21.204 (4) Å	0.50 × 0.22 × 0.16 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	4018 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3116 reflections with I > 2σ(I)
T_min = 0.932, T_max = 0.956	R_int = 0.024
11900 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.048	H-atom parameters constrained
wR(F²) = 0.140	Δρ_max = 0.24 e Å⁻³
S = 1.04	Δρ_min = −0.14 e Å⁻³
4018 reflections	Absolute structure: Flack (1983), 1705 Friedel pairs
282 parameters	Absolute structure parameter: −0.04 (15)
6 restraints

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	U_iso*/U_eq	Occ. (<1)
C1	0.1755 (4)	0.9731 (2)	0.01052 (13)	0.0561 (7)
H1A	0.2538	1.0274	0.0167	0.067*
C2	0.0221 (4)	0.99883 (18)	−0.03236 (13)	0.0533 (6)
H2A	−0.0508	0.9431	−0.0409	0.064*
C3	−0.0896 (4)	1.07522 (18)	−0.00178 (13)	0.0510 (6)
H3A	−0.0239	1.1348	−0.0008	0.061*
C4	−0.1426 (4)	1.04628 (18)	0.06463 (13)	0.0528 (7)
H4A	−0.2280	0.9943	0.0626	0.063*
C5	0.0189 (4)	1.01584 (19)	0.10235 (13)	0.0568 (7)
H5A	0.1002	1.0693	0.1064	0.068*
C6	−0.0264 (5)	0.9797 (2)	0.16670 (14)	0.0681 (8)
H6A	0.0792	0.9560	0.1874	0.082*
H6B	−0.0755	1.0301	0.1923	0.082*
C7	−0.2576 (6)	0.8854 (3)	0.20918 (16)	0.0835 (10)
C8	−0.3918 (7)	0.8146 (3)	0.1925 (2)	0.1123 (16)
H8A	−0.4642	0.8014	0.2287	0.169*
H8B	−0.3340	0.7578	0.1790	0.169*
H8C	−0.4648	0.8383	0.1590	0.169*
C9	−0.3865 (5)	1.1182 (3)	0.11907 (16)	0.0731 (9)
C10	−0.4441 (6)	1.2082 (3)	0.14768 (19)	0.0982 (12)
H10A	−0.5614	1.2011	0.1647	0.147*
H10B	−0.4447	1.2566	0.1161	0.147*
H10C	−0.3636	1.2253	0.1808	0.147*
C11	−0.3081 (4)	1.1719 (2)	−0.05358 (14)	0.0629 (8)
C12	−0.4690 (5)	1.1648 (3)	−0.09423 (18)	0.0873 (11)
H12A	−0.5117	1.2269	−0.1038	0.131*
H12B	−0.5595	1.1303	−0.0724	0.131*
H12C	−0.4394	1.1328	−0.1327	0.131*
C13	0.0893 (4)	0.9785 (2)	−0.14137 (14)	0.0649 (8)
C14	0.1764 (6)	1.0232 (3)	−0.19647 (15)	0.0890 (11)
H14A	0.1723	0.9810	−0.2318	0.133*
H14B	0.2977	1.0371	−0.1863	0.133*
H14C	0.1155	1.0805	−0.2069	0.133*
C15	0.4186 (5)	0.8690 (3)	0.02034 (18)	0.0858 (11)
H15A	0.3777	0.8406	0.0593	0.103*
H15B	0.4904	0.9234	0.0311	0.103*
C16	0.5271 (5)	0.8010 (3)	−0.0143 (2)	0.0939 (12)
H16A	0.6003	0.7662	0.0153	0.113*
H16B	0.4502	0.7564	−0.0356	0.113*
C17	0.5595 (11)	0.8630 (5)	−0.1191 (2)	0.117 (2)	0.70
H17A	0.5916	0.9248	−0.1349	0.140*	0.70
H17B	0.4313	0.8569	−0.1185	0.140*	0.70
C18	0.6461 (7)	0.7849 (4)	−0.1571 (2)	0.106 (2)	0.70
H18A	0.6190	0.7244	−0.1381	0.127*	0.70
H18B	0.7739	0.7930	−0.1566	0.127*	0.70
Cl1	0.5667 (5)	0.7865 (3)	−0.23801 (13)	0.1242 (10)	0.70
C17'	0.556 (3)	0.8083 (14)	−0.1155 (5)	0.125 (4)*	0.30
H17C	0.4302	0.8229	−0.1149	0.150*	0.30
H17D	0.5673	0.7403	−0.1149	0.150*	0.30
C18'	0.634 (2)	0.8447 (14)	−0.1780 (5)	0.125 (4)*	0.30
H18C	0.7555	0.8237	−0.1822	0.150*	0.30
H18D	0.6327	0.9130	−0.1782	0.150*	0.30
Cl1'	0.5049 (10)	0.8012 (7)	−0.2426 (4)	0.109 (3)*	0.30
O1	0.1055 (3)	0.94203 (13)	0.06919 (9)	0.0574 (5)
O2	−0.1540 (3)	0.90570 (15)	0.15955 (9)	0.0677 (6)
O3	−0.2416 (5)	0.9234 (2)	0.25869 (13)	0.1206 (11)
O4	−0.2231 (3)	1.12583 (13)	0.09468 (9)	0.0610 (5)
O5	−0.4716 (4)	1.0471 (2)	0.11726 (17)	0.1170 (11)
O6	−0.2470 (3)	1.08482 (13)	−0.03989 (9)	0.0584 (5)
O7	−0.2418 (4)	1.24259 (16)	−0.03553 (13)	0.0889 (8)
O8	0.0921 (3)	1.03612 (13)	−0.09056 (9)	0.0583 (5)
O9	0.0267 (4)	0.90214 (19)	−0.14093 (12)	0.0970 (9)
O10	0.2679 (3)	0.89899 (14)	−0.01624 (10)	0.0624 (5)
O11	0.6350 (4)	0.8454 (3)	−0.05836 (16)	0.1156 (10)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0485 (15)	0.0545 (16)	0.0653 (16)	−0.0021 (14)	0.0042 (13)	−0.0006 (14)
C2	0.0530 (16)	0.0462 (14)	0.0606 (15)	−0.0032 (12)	0.0048 (13)	−0.0032 (12)
C3	0.0485 (15)	0.0427 (13)	0.0618 (15)	−0.0042 (12)	−0.0019 (13)	−0.0019 (12)
C4	0.0554 (16)	0.0424 (13)	0.0608 (15)	−0.0020 (13)	0.0029 (13)	−0.0095 (12)
C5	0.0564 (16)	0.0522 (15)	0.0618 (15)	−0.0027 (14)	−0.0002 (14)	−0.0060 (13)
C6	0.079 (2)	0.0680 (18)	0.0573 (16)	0.0038 (19)	−0.0069 (15)	−0.0057 (15)
C7	0.096 (3)	0.091 (3)	0.063 (2)	0.002 (2)	0.014 (2)	0.0059 (19)
C8	0.129 (4)	0.114 (3)	0.094 (3)	−0.038 (3)	0.021 (3)	0.013 (2)
C9	0.063 (2)	0.078 (2)	0.077 (2)	0.005 (2)	0.0022 (17)	−0.0216 (18)
C10	0.089 (3)	0.103 (3)	0.103 (3)	0.024 (2)	0.005 (2)	−0.039 (2)
C11	0.0656 (19)	0.062 (2)	0.0616 (17)	0.0128 (16)	0.0067 (15)	0.0019 (15)
C12	0.079 (2)	0.092 (2)	0.091 (2)	0.027 (2)	−0.016 (2)	0.001 (2)
C13	0.0557 (17)	0.073 (2)	0.0663 (18)	0.0036 (17)	0.0045 (15)	−0.0106 (16)
C14	0.100 (3)	0.105 (3)	0.0617 (18)	0.009 (3)	0.0110 (19)	0.0005 (19)
C15	0.0603 (19)	0.104 (3)	0.093 (2)	0.024 (2)	−0.0085 (19)	−0.009 (2)
C16	0.060 (2)	0.090 (3)	0.132 (3)	0.012 (2)	0.009 (2)	0.009 (2)
C17	0.114 (5)	0.088 (4)	0.148 (7)	0.032 (4)	0.001 (5)	0.005 (4)
C18	0.065 (3)	0.076 (3)	0.177 (7)	0.002 (3)	0.024 (4)	0.014 (4)
Cl1	0.145 (3)	0.139 (2)	0.0891 (13)	−0.035 (2)	0.0098 (17)	0.0194 (12)
O1	0.0567 (11)	0.0563 (11)	0.0592 (10)	0.0046 (10)	0.0045 (9)	0.0007 (9)
O2	0.0847 (14)	0.0658 (12)	0.0525 (10)	−0.0044 (12)	0.0109 (10)	−0.0010 (9)
O3	0.142 (3)	0.152 (3)	0.0684 (16)	−0.023 (2)	0.0269 (18)	−0.0157 (17)
O4	0.0615 (12)	0.0511 (10)	0.0703 (11)	0.0006 (10)	0.0083 (10)	−0.0140 (10)
O5	0.0772 (16)	0.103 (2)	0.171 (3)	−0.0158 (17)	0.0454 (19)	−0.047 (2)
O6	0.0555 (11)	0.0503 (10)	0.0693 (11)	0.0037 (10)	−0.0078 (10)	−0.0021 (9)
O7	0.0963 (18)	0.0514 (13)	0.1189 (19)	0.0061 (13)	−0.0167 (16)	−0.0007 (13)
O8	0.0637 (12)	0.0525 (10)	0.0588 (10)	−0.0018 (10)	0.0076 (9)	0.0005 (9)
O9	0.113 (2)	0.0815 (16)	0.0962 (17)	−0.0266 (17)	0.0265 (16)	−0.0324 (14)
O10	0.0503 (11)	0.0623 (12)	0.0747 (12)	0.0105 (10)	0.0024 (10)	−0.0038 (10)
O11	0.0740 (17)	0.148 (3)	0.125 (2)	−0.0122 (19)	0.0188 (18)	−0.013 (2)

Geometric parameters (Å, º) top

C1—O10	1.383 (3)	C11—O6	1.351 (4)
C1—O1	1.421 (3)	C11—C12	1.492 (5)
C1—C2	1.516 (4)	C12—H12A	0.9600
C1—H1A	0.9800	C12—H12B	0.9600
C2—O8	1.443 (3)	C12—H12C	0.9600
C2—C3	1.518 (4)	C13—O9	1.182 (4)
C2—H2A	0.9800	C13—O8	1.353 (4)
C3—O6	1.442 (3)	C13—C14	1.483 (5)
C3—C4	1.521 (4)	C14—H14A	0.9600
C3—H3A	0.9800	C14—H14B	0.9600
C4—O4	1.432 (3)	C14—H14C	0.9600
C4—C5	1.519 (4)	C15—O10	1.440 (4)
C4—H4A	0.9800	C15—C16	1.462 (5)
C5—O1	1.421 (3)	C15—H15A	0.9700
C5—C6	1.497 (4)	C15—H15B	0.9700
C5—H5A	0.9800	C16—O11	1.390 (5)
C6—O2	1.432 (4)	C16—H16A	0.9700
C6—H6A	0.9700	C16—H16B	0.9700
C6—H6B	0.9700	C17—O11	1.430 (4)
C7—O3	1.186 (4)	C17—C18	1.518 (4)
C7—O2	1.342 (4)	C17—H17A	0.9700
C7—C8	1.469 (6)	C17—H17B	0.9700
C8—H8A	0.9600	C18—Cl1	1.817 (4)
C8—H8B	0.9600	C18—H18A	0.9700
C8—H8C	0.9600	C18—H18B	0.9700
C9—O5	1.197 (4)	C17'—O11	1.450 (5)
C9—O4	1.340 (4)	C17'—C18'	1.536 (5)
C9—C10	1.479 (5)	C17'—H17C	0.9700
C10—H10A	0.9600	C17'—H17D	0.9700
C10—H10B	0.9600	C18'—Cl1'	1.789 (5)
C10—H10C	0.9600	C18'—H18C	0.9700
C11—O7	1.184 (4)	C18'—H18D	0.9700

O10—C1—O1	108.1 (2)	H12A—C12—H12B	109.5
O10—C1—C2	108.7 (2)	C11—C12—H12C	109.5
O1—C1—C2	108.5 (2)	H12A—C12—H12C	109.5
O10—C1—H1A	110.5	H12B—C12—H12C	109.5
O1—C1—H1A	110.5	O9—C13—O8	123.7 (3)
C2—C1—H1A	110.5	O9—C13—C14	125.1 (3)
O8—C2—C1	108.8 (2)	O8—C13—C14	111.2 (3)
O8—C2—C3	107.8 (2)	C13—C14—H14A	109.5
C1—C2—C3	109.8 (2)	C13—C14—H14B	109.5
O8—C2—H2A	110.1	H14A—C14—H14B	109.5
C1—C2—H2A	110.1	C13—C14—H14C	109.5
C3—C2—H2A	110.1	H14A—C14—H14C	109.5
O6—C3—C2	106.5 (2)	H14B—C14—H14C	109.5
O6—C3—C4	109.1 (2)	O10—C15—C16	111.5 (3)
C2—C3—C4	110.4 (2)	O10—C15—H15A	109.3
O6—C3—H3A	110.2	C16—C15—H15A	109.3
C2—C3—H3A	110.2	O10—C15—H15B	109.3
C4—C3—H3A	110.2	C16—C15—H15B	109.3
O4—C4—C5	109.3 (2)	H15A—C15—H15B	108.0
O4—C4—C3	108.1 (2)	O11—C16—C15	111.5 (3)
C5—C4—C3	110.7 (2)	O11—C16—H16A	109.3
O4—C4—H4A	109.6	C15—C16—H16A	109.3
C5—C4—H4A	109.6	O11—C16—H16B	109.3
C3—C4—H4A	109.6	C15—C16—H16B	109.3
O1—C5—C6	107.7 (2)	H16A—C16—H16B	108.0
O1—C5—C4	108.5 (2)	O11—C17—C18	100.3 (4)
C6—C5—C4	113.2 (3)	O11—C17—H17A	111.7
O1—C5—H5A	109.1	C18—C17—H17A	111.7
C6—C5—H5A	109.1	O11—C17—H17B	111.7
C4—C5—H5A	109.1	C18—C17—H17B	111.7
O2—C6—C5	107.9 (2)	H17A—C17—H17B	109.5
O2—C6—H6A	110.1	C17—C18—Cl1	110.5 (4)
C5—C6—H6A	110.1	C17—C18—H18A	109.5
O2—C6—H6B	110.1	Cl1—C18—H18A	109.5
C5—C6—H6B	110.1	C17—C18—H18B	109.5
H6A—C6—H6B	108.4	Cl1—C18—H18B	109.5
O3—C7—O2	122.5 (4)	H18A—C18—H18B	108.1
O3—C7—C8	126.4 (4)	O11—C17'—C18'	116.2 (9)
O2—C7—C8	111.1 (3)	O11—C17'—H17C	108.2
C7—C8—H8A	109.5	C18'—C17'—H17C	108.2
C7—C8—H8B	109.5	O11—C17'—H17D	108.2
H8A—C8—H8B	109.5	C18'—C17'—H17D	108.2
C7—C8—H8C	109.5	H17C—C17'—H17D	107.4
H8A—C8—H8C	109.5	C17'—C18'—Cl1'	109.7 (8)
H8B—C8—H8C	109.5	C17'—C18'—H18C	109.7
O5—C9—O4	123.2 (3)	Cl1'—C18'—H18C	109.7
O5—C9—C10	125.8 (3)	C17'—C18'—H18D	109.7
O4—C9—C10	111.0 (3)	Cl1'—C18'—H18D	109.7
C9—C10—H10A	109.5	H18C—C18'—H18D	108.2
C9—C10—H10B	109.5	C1—O1—C5	112.0 (2)
H10A—C10—H10B	109.5	C7—O2—C6	117.7 (3)
C9—C10—H10C	109.5	C9—O4—C4	119.9 (2)
H10A—C10—H10C	109.5	C11—O6—C3	119.2 (2)
H10B—C10—H10C	109.5	C13—O8—C2	117.0 (2)
O7—C11—O6	124.2 (3)	C1—O10—C15	113.6 (2)
O7—C11—C12	126.0 (3)	C16—O11—C17	116.9 (5)
O6—C11—C12	109.9 (3)	C16—O11—C17'	99.1 (7)
C11—C12—H12A	109.5	C17—O11—C17'	31.4 (8)
C11—C12—H12B	109.5

O10—C1—C2—O8	−66.3 (3)	O3—C7—O2—C6	−3.4 (6)
O1—C1—C2—O8	176.4 (2)	C8—C7—O2—C6	174.6 (3)
O10—C1—C2—C3	175.9 (2)	C5—C6—O2—C7	−157.5 (3)
O1—C1—C2—C3	58.6 (3)	O5—C9—O4—C4	0.0 (5)
O8—C2—C3—O6	70.8 (3)	C10—C9—O4—C4	−180.0 (3)
C1—C2—C3—O6	−170.8 (2)	C5—C4—O4—C9	−115.0 (3)
O8—C2—C3—C4	−170.8 (2)	C3—C4—O4—C9	124.5 (3)
C1—C2—C3—C4	−52.4 (3)	O7—C11—O6—C3	−1.0 (4)
O6—C3—C4—O4	−72.1 (3)	C12—C11—O6—C3	178.9 (3)
C2—C3—C4—O4	171.1 (2)	C2—C3—O6—C11	−137.0 (2)
O6—C3—C4—C5	168.3 (2)	C4—C3—O6—C11	103.8 (3)
C2—C3—C4—C5	51.5 (3)	O9—C13—O8—C2	3.3 (5)
O4—C4—C5—O1	−175.2 (2)	C14—C13—O8—C2	−176.0 (3)
C3—C4—C5—O1	−56.3 (3)	C1—C2—O8—C13	103.5 (3)
O4—C4—C5—C6	65.3 (3)	C3—C2—O8—C13	−137.4 (2)
C3—C4—C5—C6	−175.7 (2)	O1—C1—O10—C15	−63.0 (3)
O1—C5—C6—O2	−65.3 (3)	C2—C1—O10—C15	179.4 (3)
C4—C5—C6—O2	54.6 (3)	C16—C15—O10—C1	−171.2 (3)
O10—C15—C16—O11	78.8 (4)	C15—C16—O11—C17	−86.4 (5)
O11—C17—C18—Cl1	177.8 (4)	C15—C16—O11—C17'	−113.8 (11)
O11—C17'—C18'—Cl1'	−173.9 (14)	C18—C17—O11—C16	−103.0 (6)
O10—C1—O1—C5	175.8 (2)	C18—C17—O11—C17'	−42.3 (17)
C2—C1—O1—C5	−66.5 (3)	C18'—C17'—O11—C16	177.2 (19)
C6—C5—O1—C1	−172.1 (2)	C18'—C17'—O11—C17	49.2 (14)
C4—C5—O1—C1	65.1 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C15—H15B···O5ⁱ	0.97	2.55	3.361 (5)	141
C18—H18B···O9ⁱ	0.97	2.48	3.335 (7)	147

Symmetry code: (i) x+1, y, z.

Experimental details

Crystal data
Chemical formula	C₁₈H₂₇ClO₁₁
M_r	454.85
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	293
a, b, c (Å)	7.5382 (13), 14.195 (3), 21.204 (4)
V (Å³)	2269.0 (8)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.22
Crystal size (mm)	0.50 × 0.22 × 0.16

Data collection
Diffractometer	Bruker SMART CCD area-detector
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.932, 0.956
No. of measured, independent and observed [I > 2σ(I)] reflections	11900, 4018, 3116
R_int	0.024
(sin θ/λ)_max (Å⁻¹)	0.597

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.048, 0.140, 1.04
No. of reflections	4018
No. of parameters	282
No. of restraints	6
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.24, −0.14
Absolute structure	Flack (1983), 1705 Friedel pairs
Absolute structure parameter	−0.04 (15)

Computer programs: SMART (Siemens, 1996), SMART, SAINT (Siemens, 1996), SHELXTL (Sheldrick, 1997), PLATON (Spek, 2003), SHELXTL and PARST95 (Nardelli, 1995).