6-(Acetoxy­meth­yl)-5-chloro-2-[(2R,3R,4R,5S)-3,4-diacet­oxy-2,5-bis­(chloro­meth­yl)-2,3,4,5-tetra­hydro­furan-2-yl­oxy]-3,4,5,6-tetra­hydro-2H-pyran-3,4-diyl diacetate toluene solvate

In sugar molecule of the title compound, C₂₂H₂₉Cl₃O₁₃·C₇H₈, the pyran­ose ring adopts the expected chair conformation. The acetoxy­methyl and two acet­oxy substituents are in the equatorial positions of this ring. In the crystal structure, there is a single weak C—H...O inter­molecular inter­action (H...O = 2.46 Å), which links mol­ecules into chains in the a-axis dirextion.

Key indicators

• Single-crystal X-ray study
• T = 294 K
• Mean [sigma](C-C) = 0.010 Å
• R factor = 0.063
• wR factor = 0.153
• Data-to-parameter ratio = 17.0

checkCIF/PLATON results

No syntax errors found



Alert level C
ABSTM02_ALERT_3_C  The ratio of expected to reported Tmax/Tmin(RR') is < 0.90
            Tmin and Tmax reported:      0.756     0.960
            Tmin(prime) and Tmax expected:      0.930     0.962
            RR(prime) =      0.815
            Please check that your absorption correction is appropriate.
PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large .............       0.81
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       3.00 Ratio
PLAT220_ALERT_2_C Large Non-Solvent    O     Ueq(max)/Ueq(min) ...       2.77 Ratio
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.51 Ratio
PLAT231_ALERT_4_C Hirshfeld Test (Solvent)   C23    -   C24     ..       6.99 su
PLAT231_ALERT_4_C Hirshfeld Test (Solvent)   C24    -   C25     ..       5.56 su
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        C21
PLAT244_ALERT_4_C Low   'Solvent' Ueq as Compared to Neighbors for        C24
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...         10
PLAT431_ALERT_2_C Short Inter HL..A Contact  Cl2    ..  O9      ..       3.25 Ang.
PLAT850_ALERT_2_C Check Flack Parameter Exact Value 0.00 and su ..       0.10

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           26.32
           From the CIF: _reflns_number_total               7000
           Count of symmetry unique reflns         3989
           Completeness (_total/calc)            175.48%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured      3011
           Fraction of Friedel pairs measured     0.755
           Are heavy atom types Z>Si present        yes

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

   0 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
   4 ALERT type 3 Indicator that the structure quality may be low
   4 ALERT type 4 Improvement, methodology, query or suggestion

---

Computing details

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1998) and PLATON (Spek,2003); software used to prepare material for publication: SHELXTL.

6-(Acetoxymethyl)-2-[(2R,3R,4R,5S)-3,4-diacetoxy-2,5-bis(chloromethyl)- 2,3,4,5-tetrahydrofuran-2-yloxy]-5-chloro-3,4,5,6-tetrahydro-2H-pyran-3,4-diyl diacetate toluene solvate

Crystal data

C22H29Cl3O13·C7H8	F(000) = 1464
Mr = 699.94	Dx = 1.345 Mg m^−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 4347 reflections
a = 8.3693 (13) Å	θ = 2.5–26.1°
b = 13.072 (2) Å	µ = 0.33 mm^−1
c = 31.603 (5) Å	T = 294 K
V = 3457.4 (9) Å^3	Prism, colorless
Z = 4	0.22 × 0.16 × 0.12 mm

Data collection

Bruker SMART-CCD area detector diffractometer	7000 independent reflections
Radiation source: fine-focus sealed tube	3951 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.057
φ and ω scans	θmax = 26.3°, θmin = 1.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→10
Tmin = 0.756, Tmax = 0.960	k = −16→16
18609 measured reflections	l = −39→24

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.063	H-atom parameters constrained
wR(F^2) = 0.153	w = 1/[σ^2(Fo^2) + (0.0387P)^2 + 3.6447P] where P = (Fo^2 + 2Fc^2)/3
S = 1.09	(Δ/σ)max = 0.003
7000 reflections	Δρmax = 0.54 e Å^−3
411 parameters	Δρmin = −0.53 e Å^−3
85 restraints	Absolute structure: Flack (1983) 3019 Friedels
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.00 (10)

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
Cl1	0.2840 (2)	0.67875 (13)	0.75256 (5)	0.0669 (4)
Cl2	−0.13401 (19)	0.77361 (11)	0.53609 (5)	0.0621 (4)
Cl3	0.6040 (2)	0.99967 (14)	0.54147 (8)	0.1070 (8)
O1	0.0582 (7)	0.3711 (3)	0.65823 (16)	0.0846 (16)
O2	0.0791 (5)	0.5309 (3)	0.63401 (12)	0.0533 (10)
O3	0.0943 (4)	0.7362 (2)	0.67020 (10)	0.0387 (8)
O4	0.5315 (4)	0.8293 (3)	0.71966 (11)	0.0488 (9)
O5	0.7083 (6)	0.8535 (4)	0.66702 (14)	0.0793 (14)
O6	0.3292 (5)	0.9725 (3)	0.67954 (12)	0.0504 (10)
O7	0.1404 (7)	1.0464 (4)	0.71937 (17)	0.0952 (17)
O8	0.2100 (4)	0.8459 (2)	0.61970 (9)	0.0343 (8)
O9	0.2153 (4)	0.8268 (2)	0.54918 (10)	0.0405 (8)
O10	0.2070 (5)	1.0821 (3)	0.52470 (11)	0.0523 (10)
O11	0.2715 (7)	1.2103 (3)	0.56887 (19)	0.0914 (16)
O12	0.0064 (4)	1.0106 (3)	0.61086 (10)	0.0430 (9)
O13	−0.0931 (5)	1.1397 (3)	0.57194 (13)	0.0635 (12)
C1	0.3543 (6)	0.6907 (4)	0.69967 (16)	0.0434 (13)
H1	0.4441	0.6436	0.6957	0.052*
C2	0.2240 (6)	0.6641 (3)	0.66745 (16)	0.0418 (12)
H2	0.2701	0.6680	0.6390	0.050*
C3	0.1403 (6)	0.8385 (3)	0.66090 (14)	0.0355 (11)
H3	0.0476	0.8841	0.6630	0.043*
C4	0.2700 (6)	0.8724 (3)	0.69174 (17)	0.0406 (12)
H4	0.2274	0.8747	0.7206	0.049*
C5	0.4108 (6)	0.7994 (4)	0.68954 (16)	0.0398 (12)
H5	0.4563	0.8008	0.6610	0.048*
C6	0.1547 (7)	0.5587 (4)	0.67368 (18)	0.0521 (15)
H6A	0.2384	0.5102	0.6807	0.062*
H6B	0.0769	0.5592	0.6964	0.062*
C7	0.0370 (8)	0.4315 (4)	0.6305 (2)	0.0579 (17)
C8	−0.0386 (8)	0.4101 (5)	0.5886 (2)	0.075 (2)
H8A	−0.1517	0.4214	0.5905	0.113*
H8B	−0.0186	0.3404	0.5807	0.113*
H8C	0.0060	0.4550	0.5676	0.113*
C9	0.6800 (7)	0.8518 (4)	0.70433 (19)	0.0494 (14)
C10	0.7928 (7)	0.8730 (5)	0.7387 (2)	0.075 (2)
H10A	0.8701	0.9223	0.7293	0.112*
H10B	0.8462	0.8109	0.7466	0.112*
H10C	0.7359	0.8997	0.7626	0.112*
C11	0.2524 (9)	1.0541 (5)	0.6955 (2)	0.0632 (17)
C12	0.3232 (10)	1.1531 (4)	0.6794 (2)	0.088 (2)
H12A	0.3445	1.1977	0.7029	0.132*
H12B	0.2491	1.1854	0.6605	0.132*
H12C	0.4211	1.1389	0.6647	0.132*
C13	0.1117 (6)	0.8525 (3)	0.58239 (14)	0.0336 (11)
C14	0.3120 (6)	0.9145 (4)	0.53856 (18)	0.0432 (13)
H14	0.3161	0.9220	0.5077	0.052*
C15	0.2293 (6)	1.0081 (4)	0.55783 (15)	0.0398 (12)
H15	0.2916	1.0367	0.5813	0.048*
C16	0.0712 (6)	0.9646 (3)	0.57325 (16)	0.0373 (12)
H16	−0.0078	0.9681	0.5504	0.045*
C17	−0.0253 (6)	0.7773 (4)	0.58385 (17)	0.0439 (13)
H17A	−0.0968	0.7961	0.6067	0.053*
H17B	0.0163	0.7096	0.5898	0.053*
C18	0.4817 (7)	0.8967 (4)	0.5555 (2)	0.068 (2)
H18A	0.5246	0.8339	0.5438	0.082*
H18B	0.4787	0.8900	0.5861	0.082*
C19	−0.0816 (7)	1.0972 (4)	0.60531 (19)	0.0464 (14)
C20	−0.1572 (8)	1.1316 (5)	0.64519 (19)	0.072 (2)
H20A	−0.2629	1.1035	0.6472	0.107*
H20B	−0.1631	1.2049	0.6455	0.107*
H20C	−0.0945	1.1086	0.6688	0.107*
C21	0.2283 (8)	1.1823 (4)	0.5353 (2)	0.0634 (17)
C22	0.1852 (10)	1.2474 (6)	0.4985 (3)	0.101 (3)
H22A	0.2743	1.2902	0.4912	0.151*
H22B	0.0952	1.2894	0.5057	0.151*
H22C	0.1583	1.2047	0.4749	0.151*
C23	0.4355 (15)	0.5347 (10)	0.5589 (3)	0.184 (5)
H23A	0.4892	0.5871	0.5430	0.277*
H23B	0.3273	0.5554	0.5643	0.277*
H23C	0.4356	0.4722	0.5429	0.277*
C24	0.5194 (11)	0.5184 (8)	0.5996 (3)	0.103 (3)
C25	0.6193 (11)	0.5915 (7)	0.6157 (3)	0.097 (3)
H25	0.6358	0.6525	0.6012	0.116*
C26	0.6930 (12)	0.5740 (8)	0.6526 (4)	0.118 (3)
H26	0.7642	0.6225	0.6629	0.141*
C27	0.6666 (13)	0.4867 (9)	0.6754 (3)	0.121 (3)
H27	0.7150	0.4788	0.7017	0.145*
C28	0.5715 (12)	0.4121 (8)	0.6603 (4)	0.115 (3)
H28	0.5569	0.3520	0.6756	0.138*
C29	0.4936 (11)	0.4261 (7)	0.6208 (4)	0.107 (3)
H29	0.4279	0.3757	0.6094	0.128*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0805 (11)	0.0765 (10)	0.0437 (8)	−0.0161 (9)	−0.0032 (9)	0.0166 (7)
Cl2	0.0634 (9)	0.0625 (9)	0.0604 (10)	−0.0065 (8)	−0.0116 (8)	−0.0087 (8)
Cl3	0.0586 (10)	0.0735 (12)	0.189 (2)	−0.0128 (10)	0.0192 (14)	0.0313 (14)
O1	0.117 (4)	0.042 (2)	0.095 (4)	−0.018 (3)	−0.019 (3)	0.014 (2)
O2	0.074 (3)	0.037 (2)	0.049 (2)	−0.002 (2)	−0.015 (2)	0.0029 (17)
O3	0.0374 (19)	0.0332 (18)	0.045 (2)	−0.0046 (16)	0.0017 (17)	0.0044 (15)
O4	0.042 (2)	0.066 (2)	0.038 (2)	−0.014 (2)	−0.0060 (18)	0.0010 (19)
O5	0.063 (3)	0.118 (4)	0.057 (3)	−0.027 (3)	0.012 (3)	−0.012 (3)
O6	0.060 (3)	0.034 (2)	0.057 (2)	−0.0081 (17)	0.004 (2)	−0.0038 (18)
O7	0.121 (5)	0.062 (3)	0.102 (4)	0.022 (3)	0.027 (4)	−0.010 (3)
O8	0.0391 (19)	0.0338 (18)	0.0301 (16)	−0.0053 (16)	−0.0020 (16)	0.0057 (14)
O9	0.0450 (19)	0.0339 (18)	0.0427 (19)	0.0016 (17)	0.0152 (18)	−0.0060 (15)
O10	0.071 (3)	0.036 (2)	0.050 (2)	0.0056 (19)	0.012 (2)	0.0198 (17)
O11	0.120 (4)	0.045 (3)	0.109 (4)	−0.009 (3)	0.003 (4)	−0.006 (3)
O12	0.054 (2)	0.0366 (19)	0.038 (2)	0.0097 (17)	0.0081 (18)	0.0022 (16)
O13	0.077 (3)	0.049 (2)	0.065 (3)	0.018 (2)	0.000 (2)	0.016 (2)
C1	0.039 (3)	0.042 (3)	0.049 (3)	−0.002 (2)	−0.006 (3)	0.003 (2)
C2	0.048 (3)	0.031 (3)	0.046 (3)	0.000 (3)	−0.010 (3)	0.000 (2)
C3	0.043 (3)	0.031 (3)	0.032 (3)	0.000 (2)	0.002 (2)	0.003 (2)
C4	0.046 (3)	0.031 (3)	0.044 (3)	−0.005 (2)	−0.002 (3)	−0.004 (2)
C5	0.042 (3)	0.042 (3)	0.035 (3)	−0.006 (2)	−0.004 (3)	−0.004 (2)
C6	0.069 (4)	0.040 (3)	0.048 (3)	−0.007 (3)	−0.013 (3)	0.011 (3)
C7	0.064 (4)	0.035 (3)	0.075 (5)	−0.005 (3)	−0.001 (4)	−0.014 (3)
C8	0.083 (5)	0.064 (4)	0.079 (5)	−0.001 (4)	−0.016 (4)	−0.025 (4)
C9	0.044 (4)	0.051 (3)	0.053 (4)	−0.016 (3)	−0.005 (3)	−0.001 (3)
C10	0.054 (4)	0.103 (5)	0.066 (4)	−0.025 (4)	−0.013 (4)	−0.013 (4)
C11	0.079 (5)	0.050 (4)	0.061 (4)	0.000 (4)	−0.011 (4)	−0.010 (3)
C12	0.120 (7)	0.039 (3)	0.104 (6)	−0.019 (4)	−0.022 (5)	−0.007 (4)
C13	0.037 (3)	0.034 (3)	0.030 (2)	0.002 (2)	0.001 (2)	−0.002 (2)
C14	0.048 (3)	0.034 (3)	0.048 (3)	−0.001 (2)	0.010 (3)	0.003 (2)
C15	0.047 (3)	0.034 (3)	0.038 (3)	−0.003 (3)	0.005 (3)	0.007 (2)
C16	0.047 (3)	0.027 (2)	0.038 (3)	0.002 (2)	0.006 (3)	−0.004 (2)
C17	0.044 (3)	0.030 (3)	0.057 (3)	−0.003 (2)	−0.003 (3)	−0.005 (2)
C18	0.046 (4)	0.047 (3)	0.110 (6)	0.000 (3)	0.011 (4)	0.022 (4)
C19	0.045 (3)	0.035 (3)	0.060 (4)	0.006 (3)	0.009 (3)	−0.006 (3)
C20	0.087 (5)	0.059 (4)	0.069 (4)	0.022 (4)	0.024 (4)	−0.002 (3)
C21	0.067 (4)	0.040 (3)	0.083 (5)	0.008 (3)	0.023 (4)	0.017 (4)
C22	0.137 (7)	0.056 (4)	0.109 (6)	0.026 (5)	0.043 (6)	0.043 (4)
C23	0.166 (8)	0.243 (9)	0.145 (8)	0.037 (8)	0.020 (7)	−0.013 (7)
C24	0.084 (5)	0.132 (6)	0.094 (5)	0.036 (5)	0.012 (5)	0.001 (5)
C25	0.078 (5)	0.087 (5)	0.125 (6)	0.006 (5)	0.025 (5)	−0.003 (5)
C26	0.089 (6)	0.127 (7)	0.138 (7)	0.018 (5)	0.028 (6)	−0.025 (6)
C27	0.107 (6)	0.138 (7)	0.118 (6)	0.031 (6)	0.017 (5)	−0.002 (6)
C28	0.108 (6)	0.097 (6)	0.140 (7)	0.013 (5)	0.031 (6)	0.019 (5)
C29	0.095 (6)	0.090 (5)	0.136 (7)	−0.008 (5)	0.026 (5)	−0.011 (5)

Geometric parameters (Å, º)

Cl1—C1	1.779 (5)	C10—H10B	0.9600
Cl2—C17	1.763 (5)	C10—H10C	0.9600
Cl3—C18	1.748 (6)	C11—C12	1.511 (9)
O1—C7	1.191 (7)	C12—H12A	0.9600
O2—C7	1.351 (6)	C12—H12B	0.9600
O2—C6	1.451 (6)	C12—H12C	0.9600
O3—C3	1.423 (5)	C13—C17	1.511 (6)
O3—C2	1.440 (6)	C13—C16	1.531 (6)
O4—C9	1.366 (6)	C14—C15	1.533 (7)
O4—C5	1.442 (6)	C14—C18	1.536 (8)
O5—C9	1.203 (7)	C14—H14	0.9800
O6—C11	1.344 (7)	C15—C16	1.520 (7)
O6—C4	1.451 (6)	C15—H15	0.9800
O7—C11	1.207 (8)	C16—H16	0.9800
O8—C3	1.430 (5)	C17—H17A	0.9700
O8—C13	1.440 (5)	C17—H17B	0.9700
O9—C13	1.402 (5)	C18—H18A	0.9700
O9—C14	1.444 (6)	C18—H18B	0.9700
O10—C21	1.364 (7)	C19—C20	1.480 (7)
O10—C15	1.437 (5)	C20—H20A	0.9600
O11—C21	1.180 (8)	C20—H20B	0.9600
O12—C19	1.361 (6)	C20—H20C	0.9600
O12—C16	1.439 (5)	C21—C22	1.483 (9)
O13—C19	1.196 (6)	C22—H22A	0.9600
C1—C5	1.531 (7)	C22—H22B	0.9600
C1—C2	1.532 (7)	C22—H22C	0.9600
C1—H1	0.9800	C23—C24	1.481 (8)
C2—C6	1.509 (7)	C23—H23A	0.9600
C2—H2	0.9800	C23—H23B	0.9600
C3—C4	1.525 (7)	C23—H23C	0.9600
C3—H3	0.9800	C24—C25	1.367 (12)
C4—C5	1.519 (7)	C24—C29	1.397 (12)
C4—H4	0.9800	C25—C26	1.339 (12)
C5—H5	0.9800	C25—H25	0.9300
C6—H6A	0.9700	C26—C27	1.369 (13)
C6—H6B	0.9700	C26—H26	0.9300
C7—C8	1.496 (9)	C27—C28	1.346 (13)
C8—H8A	0.9600	C27—H27	0.9300
C8—H8B	0.9600	C28—C29	1.422 (13)
C8—H8C	0.9600	C28—H28	0.9300
C9—C10	1.465 (8)	C29—H29	0.9300
C10—H10A	0.9600
C7—O2—C6	115.2 (4)	O8—C13—C16	109.8 (4)
C3—O3—C2	113.5 (4)	C17—C13—C16	117.4 (4)
C9—O4—C5	117.5 (4)	O9—C14—C15	106.8 (4)
C11—O6—C4	116.9 (5)	O9—C14—C18	108.5 (4)
C3—O8—C13	121.1 (4)	C15—C14—C18	113.6 (5)
C13—O9—C14	109.3 (3)	O9—C14—H14	109.3
C21—O10—C15	116.8 (5)	C15—C14—H14	109.3
C19—O12—C16	116.5 (4)	C18—C14—H14	109.3
C5—C1—C2	106.9 (4)	O10—C15—C16	111.9 (4)
C5—C1—Cl1	112.3 (4)	O10—C15—C14	107.8 (4)
C2—C1—Cl1	111.7 (4)	C16—C15—C14	102.8 (4)
C5—C1—H1	108.6	O10—C15—H15	111.3
C2—C1—H1	108.6	C16—C15—H15	111.3
Cl1—C1—H1	108.6	C14—C15—H15	111.3
O3—C2—C6	107.4 (4)	O12—C16—C15	115.9 (4)
O3—C2—C1	110.4 (4)	O12—C16—C13	109.2 (4)
C6—C2—C1	113.2 (4)	C15—C16—C13	103.1 (4)
O3—C2—H2	108.6	O12—C16—H16	109.5
C6—C2—H2	108.6	C15—C16—H16	109.5
C1—C2—H2	108.6	C13—C16—H16	109.5
O3—C3—O8	111.2 (4)	C13—C17—Cl2	112.6 (4)
O3—C3—C4	109.5 (4)	C13—C17—H17A	109.1
O8—C3—C4	105.8 (4)	Cl2—C17—H17A	109.1
O3—C3—H3	110.1	C13—C17—H17B	109.1
O8—C3—H3	110.1	Cl2—C17—H17B	109.1
C4—C3—H3	110.1	H17A—C17—H17B	107.8
O6—C4—C5	106.9 (4)	C14—C18—Cl3	109.6 (4)
O6—C4—C3	109.6 (4)	C14—C18—H18A	109.7
C5—C4—C3	109.9 (4)	Cl3—C18—H18A	109.7
O6—C4—H4	110.1	C14—C18—H18B	109.7
C5—C4—H4	110.1	Cl3—C18—H18B	109.7
C3—C4—H4	110.1	H18A—C18—H18B	108.2
O4—C5—C4	110.1 (4)	O13—C19—O12	122.9 (5)
O4—C5—C1	109.3 (4)	O13—C19—C20	125.1 (5)
C4—C5—C1	109.5 (4)	O12—C19—C20	112.0 (5)
O4—C5—H5	109.3	C19—C20—H20A	109.5
C4—C5—H5	109.3	C19—C20—H20B	109.5
C1—C5—H5	109.3	H20A—C20—H20B	109.5
O2—C6—C2	106.5 (4)	C19—C20—H20C	109.5
O2—C6—H6A	110.4	H20A—C20—H20C	109.5
C2—C6—H6A	110.4	H20B—C20—H20C	109.5
O2—C6—H6B	110.4	O11—C21—O10	123.9 (6)
C2—C6—H6B	110.4	O11—C21—C22	126.9 (7)
H6A—C6—H6B	108.6	O10—C21—C22	109.1 (7)
O1—C7—O2	122.5 (6)	C21—C22—H22A	109.5
O1—C7—C8	126.2 (6)	C21—C22—H22B	109.5
O2—C7—C8	111.2 (6)	H22A—C22—H22B	109.5
C7—C8—H8A	109.5	C21—C22—H22C	109.5
C7—C8—H8B	109.5	H22A—C22—H22C	109.5
H8A—C8—H8B	109.5	H22B—C22—H22C	109.5
C7—C8—H8C	109.5	C24—C23—H23A	109.5
H8A—C8—H8C	109.5	C24—C23—H23B	109.5
H8B—C8—H8C	109.5	H23A—C23—H23B	109.5
O5—C9—O4	122.1 (5)	C24—C23—H23C	109.5
O5—C9—C10	126.6 (6)	H23A—C23—H23C	109.5
O4—C9—C10	111.4 (5)	H23B—C23—H23C	109.5
C9—C10—H10A	109.5	C25—C24—C29	121.3 (9)
C9—C10—H10B	109.5	C25—C24—C23	120.8 (11)
H10A—C10—H10B	109.5	C29—C24—C23	117.9 (11)
C9—C10—H10C	109.5	C26—C25—C24	119.1 (10)
H10A—C10—H10C	109.5	C26—C25—H25	120.4
H10B—C10—H10C	109.5	C24—C25—H25	120.4
O7—C11—O6	122.6 (6)	C25—C26—C27	121.8 (11)
O7—C11—C12	125.9 (6)	C25—C26—H26	119.1
O6—C11—C12	111.4 (6)	C27—C26—H26	119.1
C11—C12—H12A	109.5	C28—C27—C26	120.8 (11)
C11—C12—H12B	109.5	C28—C27—H27	119.6
H12A—C12—H12B	109.5	C26—C27—H27	119.6
C11—C12—H12C	109.5	C27—C28—C29	119.3 (10)
H12A—C12—H12C	109.5	C27—C28—H28	120.4
H12B—C12—H12C	109.5	C29—C28—H28	120.4
O9—C13—O8	104.2 (4)	C24—C29—C28	117.5 (9)
O9—C13—C17	109.6 (4)	C24—C29—H29	121.2
O8—C13—C17	111.7 (4)	C28—C29—H29	121.2
O9—C13—C16	103.0 (4)
C3—O3—C2—C6	−174.4 (4)	C3—O8—C13—C17	−44.0 (5)
C3—O3—C2—C1	61.7 (5)	C3—O8—C13—C16	87.9 (5)
C5—C1—C2—O3	−59.0 (5)	C13—O9—C14—C15	−17.1 (5)
Cl1—C1—C2—O3	64.3 (5)	C13—O9—C14—C18	105.7 (5)
C5—C1—C2—C6	−179.4 (5)	C21—O10—C15—C16	105.9 (5)
Cl1—C1—C2—C6	−56.2 (5)	C21—O10—C15—C14	−141.8 (5)
C2—O3—C3—O8	57.2 (5)	O9—C14—C15—O10	−126.5 (4)
C2—O3—C3—C4	−59.3 (5)	C18—C14—C15—O10	113.9 (5)
C13—O8—C3—O3	81.7 (5)	O9—C14—C15—C16	−8.2 (5)
C13—O8—C3—C4	−159.5 (4)	C18—C14—C15—C16	−127.7 (5)
C11—O6—C4—C5	−152.4 (5)	C19—O12—C16—C15	84.5 (5)
C11—O6—C4—C3	88.6 (5)	C19—O12—C16—C13	−159.7 (4)
O3—C3—C4—O6	173.9 (4)	O10—C15—C16—O12	−97.5 (5)
O8—C3—C4—O6	54.0 (5)	C14—C15—C16—O12	147.1 (4)
O3—C3—C4—C5	56.8 (5)	O10—C15—C16—C13	143.4 (4)
O8—C3—C4—C5	−63.1 (5)	C14—C15—C16—C13	27.9 (5)
C9—O4—C5—C4	−121.0 (5)	O9—C13—C16—O12	−162.6 (4)
C9—O4—C5—C1	118.8 (5)	O8—C13—C16—O12	−52.0 (5)
O6—C4—C5—O4	63.1 (5)	C17—C13—C16—O12	76.9 (5)
C3—C4—C5—O4	−178.1 (4)	O9—C13—C16—C15	−38.9 (5)
O6—C4—C5—C1	−176.8 (4)	O8—C13—C16—C15	71.7 (5)
C3—C4—C5—C1	−58.0 (5)	C17—C13—C16—C15	−159.4 (4)
C2—C1—C5—O4	178.7 (4)	O9—C13—C17—Cl2	−58.3 (5)
Cl1—C1—C5—O4	55.8 (5)	O8—C13—C17—Cl2	−173.3 (3)
C2—C1—C5—C4	58.1 (5)	C16—C13—C17—Cl2	58.7 (5)
Cl1—C1—C5—C4	−64.8 (5)	O9—C14—C18—Cl3	177.8 (4)
C7—O2—C6—C2	167.7 (5)	C15—C14—C18—Cl3	−63.6 (6)
O3—C2—C6—O2	77.5 (5)	C16—O12—C19—O13	−7.2 (8)
C1—C2—C6—O2	−160.4 (4)	C16—O12—C19—C20	173.7 (5)
C6—O2—C7—O1	1.1 (9)	C15—O10—C21—O11	4.2 (10)
C6—O2—C7—C8	−179.6 (5)	C15—O10—C21—C22	−174.5 (5)
C5—O4—C9—O5	4.8 (8)	C29—C24—C25—C26	−0.3 (13)
C5—O4—C9—C10	−175.6 (5)	C23—C24—C25—C26	180.0 (9)
C4—O6—C11—O7	0.9 (8)	C24—C25—C26—C27	−2.5 (14)
C4—O6—C11—C12	−178.5 (5)	C25—C26—C27—C28	3.7 (15)
C14—O9—C13—O8	−79.7 (4)	C26—C27—C28—C29	−2.1 (15)
C14—O9—C13—C17	160.6 (4)	C25—C24—C29—C28	1.8 (13)
C14—O9—C13—C16	34.9 (5)	C23—C24—C29—C28	−178.5 (8)
C3—O8—C13—O9	−162.3 (3)	C27—C28—C29—C24	−0.6 (14)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C22—H22A···O13^i	0.96	2.46	3.252 (10)	140

Symmetry code: (i) x+1/2, −y+5/2, −z+1.