(–)-Nomilin chloro­form solvate

The absolute stereochemistry of the title compound, C₂₈H₃₃O₉·CHCl₃, has been determined by single-crystal X-ray diffraction by incorporation of the heavy-atom-containing solvent chloro­form. The A/B, B/C and C/D ring junctions are all trans-fused. Five-membered ring E is equatorially attached to ring D. The crystal structure is stabilized by weak inter­molecular C—H...O inter­actions.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.007 Å
• Disorder in solvent or counterion
• R factor = 0.054
• wR factor = 0.165
• Data-to-parameter ratio = 13.3

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.73 Ratio
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         O9
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C18
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C22
PLAT244_ALERT_4_C Low   'Solvent' Ueq as Compared to Neighbors for        C29
PLAT302_ALERT_4_C Anion/Solvent Disorder .........................      43.00 Perc.
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          7
PLAT480_ALERT_4_C Long H...A H-Bond Reported H24C   ..  O5      ..       2.76 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H11B   ..  O8      ..       2.67 Ang.
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      22.80 Deg.
              CL3' -C29  -CL3     1.555   1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      18.40 Deg.
              CL1' -C29  -CL1     1.555   1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      27.90 Deg.
              CL2' -C29  -CL2     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           25.01
           From the CIF: _reflns_number_total               5361
           Count of symmetry unique reflns         3058
           Completeness (_total/calc)            175.31%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured      2303
           Fraction of Friedel pairs measured     0.753
           Are heavy atom types Z>Si present        yes

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
  12 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
   7 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

---

Computing details

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); 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, 2000); software used to prepare material for publication: SHELXTL.

(-)-Nomilin chloroform solvate

Crystal data

C28H33O9·CHCl3	F(000) = 1324
Mr = 632.91	Dx = 1.385 Mg m^−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 3156 reflections
a = 8.599 (4) Å	θ = 2.5–19.9°
b = 12.951 (6) Å	µ = 0.35 mm^−1
c = 27.252 (12) Å	T = 298 K
V = 3035 (2) Å^3	Prism, colourless
Z = 4	0.45 × 0.38 × 0.31 mm

Data collection

Bruker SMART CCD area-detector diffractometer	5361 independent reflections
Radiation source: fine-focus sealed tube	3162 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.050
φ and ω scans	θmax = 25.0°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −10→10
Tmin = 0.857, Tmax = 0.898	k = −15→14
16041 measured reflections	l = −27→32

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)] = 0.054	H-atom parameters constrained
wR(F^2) = 0.165	w = 1/[σ^2(Fo^2) + (0.0796P)^2 + 0.9994P] where P = (Fo^2 + 2Fc^2)/3
S = 1.00	(Δ/σ)max = 0.016
5361 reflections	Δρmax = 0.32 e Å^−3
404 parameters	Δρmin = −0.29 e Å^−3
138 restraints	Absolute structure: Flack (1983), 2303 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.10 (14)

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	Occ. (<1)
Cl1	0.9764 (13)	0.5117 (5)	0.3464 (5)	0.139 (3)	0.615 (19)
Cl2	0.8483 (10)	0.3190 (5)	0.3254 (4)	0.173 (3)	0.615 (19)
Cl3	1.0178 (11)	0.3485 (11)	0.4127 (3)	0.179 (4)	0.615 (19)
Cl1'	1.004 (2)	0.5093 (9)	0.3643 (8)	0.150 (5)	0.385 (19)
Cl2'	0.910 (2)	0.3440 (14)	0.3051 (6)	0.207 (5)	0.385 (19)
Cl3'	0.998 (2)	0.3059 (11)	0.4008 (5)	0.174 (5)	0.385 (19)
O1	−0.0023 (4)	0.2984 (2)	0.72700 (10)	0.0534 (8)
O2	−0.1624 (5)	0.1963 (3)	0.69016 (13)	0.0731 (11)
O3	0.0345 (3)	0.3556 (2)	0.60736 (10)	0.0485 (8)
O4	−0.1338 (6)	0.3518 (4)	0.54467 (16)	0.1087 (16)
O5	0.5194 (4)	0.5546 (3)	0.67950 (12)	0.0659 (9)
O6	0.3947 (4)	0.7595 (2)	0.58078 (11)	0.0513 (8)
O7	0.6450 (4)	0.6671 (3)	0.52380 (12)	0.0612 (9)
O8	0.7971 (4)	0.7337 (3)	0.58006 (13)	0.0726 (10)
O9	0.6380 (7)	0.4822 (4)	0.40481 (18)	0.1157 (18)
C1	−0.1146 (6)	0.2837 (4)	0.69400 (16)	0.0517 (12)
C2	−0.1776 (6)	0.3694 (3)	0.66366 (17)	0.0530 (12)
H2A	−0.2832	0.3850	0.6632	0.064*
C3	−0.0612 (5)	0.4304 (3)	0.63345 (14)	0.0407 (10)
H3A	−0.1201	0.4691	0.6088	0.049*
C4	0.0463 (5)	0.5074 (3)	0.65964 (14)	0.0380 (9)
C5	0.1660 (5)	0.5466 (3)	0.62080 (13)	0.0363 (9)
H5A	0.2250	0.4846	0.6119	0.044*
C6	0.2930 (5)	0.6240 (3)	0.63898 (14)	0.0377 (10)
C7	0.3791 (5)	0.5664 (3)	0.67925 (15)	0.0441 (10)
C8	0.2780 (5)	0.5226 (3)	0.71881 (15)	0.0475 (11)
H8A	0.2319	0.5791	0.7371	0.057*
H8B	0.3424	0.4834	0.7413	0.057*
C9	0.1460 (5)	0.4516 (3)	0.69945 (14)	0.0421 (10)
H9A	0.1992	0.3957	0.6820	0.051*
C10	0.0637 (6)	0.3985 (3)	0.74359 (15)	0.0507 (12)
C11	0.1067 (5)	0.5876 (3)	0.57168 (15)	0.0459 (11)
H11A	0.0096	0.5539	0.5632	0.055*
H11B	0.0877	0.6613	0.5741	0.055*
C12	0.2281 (5)	0.5665 (4)	0.53206 (15)	0.0494 (11)
H12A	0.2093	0.6125	0.5046	0.059*
H12B	0.2151	0.4963	0.5204	0.059*
C13	0.3985 (5)	0.5807 (3)	0.54956 (14)	0.0418 (10)
C14	0.3973 (5)	0.6516 (3)	0.59457 (14)	0.0391 (10)
C15	0.5340 (5)	0.7188 (3)	0.60161 (17)	0.0483 (11)
H15A	0.5574	0.7393	0.6354	0.058*
C16	0.6683 (6)	0.7070 (4)	0.56815 (19)	0.0533 (12)
C17	0.4901 (6)	0.6359 (3)	0.50815 (15)	0.0503 (11)
H17A	0.4322	0.6978	0.4983	0.060*
C18	0.5167 (7)	0.5701 (4)	0.46333 (17)	0.0595 (13)
C19	0.6545 (9)	0.5410 (5)	0.4459 (2)	0.099 (2)
H19A	0.7495	0.5584	0.4599	0.119*
C20	0.4843 (11)	0.4750 (5)	0.3971 (2)	0.091 (2)
H20A	0.4390	0.4384	0.3715	0.109*
C21	0.4057 (9)	0.5269 (5)	0.43090 (19)	0.0859 (19)
H21A	0.2982	0.5336	0.4329	0.103*
C22	−0.0149 (8)	0.3236 (4)	0.56235 (19)	0.0652 (14)
C23	0.1015 (8)	0.2550 (5)	0.53875 (19)	0.0839 (18)
H23A	0.0515	0.2141	0.5139	0.126*
H23B	0.1464	0.2103	0.5630	0.126*
H23C	0.1818	0.2961	0.5240	0.126*
C24	−0.0598 (5)	0.5954 (3)	0.67788 (16)	0.0507 (12)
H24A	−0.0701	0.6465	0.6526	0.076*
H24B	−0.0148	0.6264	0.7066	0.076*
H24C	−0.1604	0.5681	0.6858	0.076*
C25	0.2318 (6)	0.7255 (3)	0.66129 (17)	0.0563 (12)
H25A	0.3174	0.7714	0.6674	0.084*
H25B	0.1793	0.7110	0.6916	0.084*
H25C	0.1605	0.7574	0.6388	0.084*
C26	0.1807 (7)	0.3583 (4)	0.78089 (18)	0.0724 (16)
H26A	0.1309	0.3089	0.8020	0.109*
H26B	0.2193	0.4147	0.8002	0.109*
H26C	0.2656	0.3257	0.7640	0.109*
C27	−0.0613 (7)	0.4595 (4)	0.77091 (17)	0.0684 (16)
H27A	−0.0906	0.4229	0.8001	0.103*
H27C	−0.1506	0.4678	0.7502	0.103*
H27D	−0.0212	0.5262	0.7796	0.103*
C28	0.4823 (6)	0.4791 (3)	0.56219 (16)	0.0527 (12)
H28C	0.4434	0.4528	0.5928	0.079*
H28D	0.5920	0.4916	0.5650	0.079*
H28A	0.4639	0.4294	0.5367	0.079*
C29	1.0102 (9)	0.3821 (5)	0.3526 (2)	0.108 (2)
H29	1.1066	0.3626	0.3359	0.130*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.115 (5)	0.091 (3)	0.210 (7)	0.011 (3)	0.071 (5)	0.031 (3)
Cl2	0.183 (5)	0.153 (4)	0.183 (5)	−0.060 (4)	0.039 (5)	−0.077 (4)
Cl3	0.154 (5)	0.212 (8)	0.170 (5)	−0.024 (5)	−0.046 (5)	0.063 (5)
Cl1'	0.122 (7)	0.094 (6)	0.234 (12)	−0.024 (5)	0.014 (8)	0.004 (6)
Cl2'	0.180 (10)	0.276 (11)	0.165 (8)	−0.054 (8)	0.004 (7)	−0.025 (8)
Cl3'	0.211 (10)	0.134 (7)	0.178 (8)	0.069 (6)	0.085 (8)	0.091 (6)
O1	0.065 (2)	0.0471 (16)	0.0477 (17)	−0.0145 (16)	−0.0056 (17)	0.0020 (14)
O2	0.090 (3)	0.057 (2)	0.072 (2)	−0.027 (2)	−0.014 (2)	0.0021 (18)
O3	0.0531 (19)	0.0502 (16)	0.0422 (16)	−0.0045 (15)	−0.0044 (15)	−0.0094 (14)
O4	0.099 (4)	0.150 (4)	0.077 (3)	0.014 (3)	−0.042 (3)	−0.033 (3)
O5	0.044 (2)	0.087 (2)	0.067 (2)	−0.0041 (19)	−0.0001 (17)	0.0213 (18)
O6	0.0534 (19)	0.0370 (16)	0.0635 (19)	0.0032 (14)	0.0097 (16)	0.0089 (14)
O7	0.057 (2)	0.069 (2)	0.057 (2)	−0.0035 (17)	0.0175 (18)	0.0064 (17)
O8	0.049 (2)	0.086 (3)	0.083 (3)	−0.0103 (19)	0.0070 (19)	0.021 (2)
O9	0.135 (5)	0.112 (4)	0.100 (3)	−0.026 (3)	0.069 (3)	−0.038 (3)
C1	0.059 (3)	0.050 (3)	0.046 (3)	−0.013 (2)	0.004 (2)	−0.002 (2)
C2	0.039 (3)	0.058 (3)	0.062 (3)	−0.006 (2)	0.004 (2)	0.009 (2)
C3	0.038 (2)	0.043 (2)	0.042 (2)	−0.001 (2)	−0.0020 (19)	−0.0016 (19)
C4	0.038 (2)	0.037 (2)	0.038 (2)	−0.0010 (18)	0.0018 (19)	0.0024 (18)
C5	0.034 (2)	0.037 (2)	0.038 (2)	−0.0005 (18)	0.0003 (18)	−0.0016 (17)
C6	0.037 (2)	0.037 (2)	0.039 (2)	−0.0015 (19)	0.0069 (19)	−0.0032 (18)
C7	0.044 (3)	0.047 (2)	0.041 (2)	−0.005 (2)	−0.001 (2)	−0.001 (2)
C8	0.046 (3)	0.057 (3)	0.039 (2)	−0.014 (2)	0.002 (2)	−0.001 (2)
C9	0.045 (3)	0.045 (2)	0.036 (2)	−0.006 (2)	−0.002 (2)	−0.0056 (19)
C10	0.066 (3)	0.048 (2)	0.039 (2)	−0.019 (2)	0.002 (2)	−0.004 (2)
C11	0.045 (3)	0.044 (2)	0.048 (2)	0.005 (2)	0.003 (2)	0.005 (2)
C12	0.057 (3)	0.051 (3)	0.040 (2)	0.003 (2)	0.005 (2)	0.005 (2)
C13	0.049 (3)	0.042 (2)	0.035 (2)	0.002 (2)	0.008 (2)	0.0049 (18)
C14	0.042 (2)	0.030 (2)	0.045 (2)	0.0038 (18)	0.004 (2)	0.0058 (18)
C15	0.045 (3)	0.048 (2)	0.052 (3)	−0.003 (2)	0.002 (2)	0.004 (2)
C16	0.041 (3)	0.054 (3)	0.065 (3)	−0.001 (2)	0.009 (3)	0.020 (3)
C17	0.057 (3)	0.053 (3)	0.041 (2)	0.002 (2)	0.009 (2)	0.009 (2)
C18	0.073 (4)	0.059 (3)	0.047 (3)	−0.002 (3)	0.022 (3)	0.008 (2)
C19	0.099 (5)	0.105 (5)	0.092 (5)	−0.021 (4)	0.049 (4)	−0.035 (4)
C20	0.131 (6)	0.096 (4)	0.044 (3)	−0.003 (5)	0.022 (4)	−0.009 (3)
C21	0.105 (5)	0.107 (5)	0.046 (3)	0.020 (4)	0.004 (3)	−0.003 (3)
C22	0.079 (4)	0.068 (3)	0.048 (3)	−0.009 (3)	−0.010 (3)	−0.012 (2)
C23	0.116 (5)	0.079 (4)	0.057 (3)	0.008 (4)	0.007 (3)	−0.022 (3)
C24	0.048 (3)	0.050 (3)	0.054 (3)	0.004 (2)	0.016 (2)	−0.003 (2)
C25	0.062 (3)	0.042 (2)	0.065 (3)	−0.003 (2)	0.019 (3)	−0.011 (2)
C26	0.086 (4)	0.080 (4)	0.051 (3)	−0.038 (3)	−0.011 (3)	0.016 (3)
C27	0.090 (4)	0.068 (3)	0.047 (3)	−0.027 (3)	0.025 (3)	−0.011 (2)
C28	0.066 (3)	0.044 (2)	0.048 (2)	0.010 (2)	0.015 (2)	0.003 (2)
C29	0.103 (5)	0.101 (5)	0.120 (5)	0.017 (4)	0.029 (5)	−0.001 (4)

Geometric parameters (Å, º)

Cl1—C29	1.712 (10)	C10—C26	1.522 (7)
Cl2—C29	1.776 (10)	C11—C12	1.527 (6)
Cl3—C29	1.696 (10)	C11—H11A	0.9700
Cl1'—C29	1.679 (13)	C11—H11B	0.9700
Cl2'—C29	1.633 (11)	C12—C13	1.552 (6)
Cl3'—C29	1.646 (11)	C12—H12A	0.9700
O1—C1	1.333 (6)	C12—H12B	0.9700
O1—C10	1.487 (5)	C13—C14	1.532 (6)
O2—C1	1.208 (5)	C13—C28	1.540 (6)
O3—C22	1.363 (6)	C13—C17	1.551 (6)
O3—C3	1.456 (5)	C14—C15	1.475 (6)
O4—C22	1.187 (7)	C15—C16	1.479 (6)
O5—C7	1.216 (5)	C15—H15A	0.9800
O6—C15	1.426 (5)	C17—C18	1.508 (6)
O6—C14	1.447 (5)	C17—H17A	0.9800
O7—C16	1.329 (6)	C18—C19	1.331 (8)
O7—C17	1.456 (6)	C18—C21	1.417 (8)
O8—C16	1.205 (6)	C19—H19A	0.9300
O9—C20	1.341 (9)	C20—C21	1.326 (8)
O9—C19	1.361 (7)	C20—H20A	0.9300
C1—C2	1.487 (7)	C21—H21A	0.9300
C2—C3	1.517 (6)	C22—C23	1.486 (8)
C2—H2A	0.9300	C23—H23A	0.9600
C3—C4	1.536 (6)	C23—H23B	0.9600
C3—H3A	0.9800	C23—H23C	0.9600
C4—C24	1.542 (6)	C24—H24A	0.9600
C4—C5	1.561 (5)	C24—H24B	0.9600
C4—C9	1.560 (6)	C24—H24C	0.9600
C5—C11	1.528 (5)	C25—H25A	0.9600
C5—C6	1.564 (5)	C25—H25B	0.9600
C5—H5A	0.9800	C25—H25C	0.9600
C6—C7	1.520 (6)	C26—H26A	0.9600
C6—C25	1.541 (6)	C26—H26B	0.9600
C6—C14	1.548 (6)	C26—H26C	0.9600
C7—C8	1.496 (6)	C27—H27A	0.9600
C8—C9	1.553 (6)	C27—H27C	0.9600
C8—H8A	0.9700	C27—H27D	0.9600
C8—H8B	0.9700	C28—H28C	0.9600
C9—C10	1.556 (6)	C28—H28D	0.9600
C9—H9A	0.9800	C28—H28A	0.9600
C10—C27	1.527 (7)	C29—H29	0.9800
C1—O1—C10	127.3 (3)	C14—C15—H15A	116.5
C22—O3—C3	117.7 (4)	C16—C15—H15A	116.5
C15—O6—C14	61.8 (3)	O8—C16—O7	119.7 (4)
C16—O7—C17	120.8 (3)	O8—C16—C15	121.5 (5)
C20—O9—C19	105.7 (5)	O7—C16—C15	118.9 (4)
O2—C1—O1	116.0 (4)	O7—C17—C18	104.8 (4)
O2—C1—C2	121.8 (5)	O7—C17—C13	112.3 (4)
O1—C1—C2	122.2 (4)	C18—C17—C13	113.9 (4)
C1—C2—C3	116.7 (4)	O7—C17—H17A	108.5
C1—C2—H2A	121.6	C18—C17—H17A	108.5
C3—C2—H2A	121.6	C13—C17—H17A	108.5
O3—C3—C2	106.9 (3)	C19—C18—C21	105.4 (5)
O3—C3—C4	108.6 (3)	C19—C18—C17	125.8 (6)
C2—C3—C4	118.9 (3)	C21—C18—C17	128.8 (5)
O3—C3—H3A	107.3	C18—C19—O9	111.0 (6)
C2—C3—H3A	107.3	C18—C19—H19A	124.5
C4—C3—H3A	107.3	O9—C19—H19A	124.5
C3—C4—C24	105.9 (3)	C21—C20—O9	111.0 (6)
C3—C4—C5	107.0 (3)	C21—C20—H20A	124.5
C24—C4—C5	111.6 (3)	O9—C20—H20A	124.5
C3—C4—C9	110.7 (3)	C20—C21—C18	106.8 (7)
C24—C4—C9	116.3 (3)	C20—C21—H21A	126.6
C5—C4—C9	105.0 (3)	C18—C21—H21A	126.6
C11—C5—C4	119.2 (3)	O4—C22—O3	122.7 (5)
C11—C5—C6	106.7 (3)	O4—C22—C23	126.0 (5)
C4—C5—C6	117.0 (3)	O3—C22—C23	111.2 (5)
C11—C5—H5A	104.0	C22—C23—H23A	109.5
C4—C5—H5A	104.0	C22—C23—H23B	109.5
C6—C5—H5A	104.0	H23A—C23—H23B	109.5
C7—C6—C25	107.5 (3)	C22—C23—H23C	109.5
C7—C6—C14	113.3 (3)	H23A—C23—H23C	109.5
C25—C6—C14	108.0 (3)	H23B—C23—H23C	109.5
C7—C6—C5	104.7 (3)	C4—C24—H24A	109.5
C25—C6—C5	115.7 (3)	C4—C24—H24B	109.5
C14—C6—C5	107.8 (3)	H24A—C24—H24B	109.5
O5—C7—C8	121.7 (4)	C4—C24—H24C	109.5
O5—C7—C6	123.3 (4)	H24A—C24—H24C	109.5
C8—C7—C6	115.0 (4)	H24B—C24—H24C	109.5
C7—C8—C9	113.8 (3)	C6—C25—H25A	109.5
C7—C8—H8A	108.8	C6—C25—H25B	109.5
C9—C8—H8A	108.8	H25A—C25—H25B	109.5
C7—C8—H8B	108.8	C6—C25—H25C	109.5
C9—C8—H8B	108.8	H25A—C25—H25C	109.5
H8A—C8—H8B	107.7	H25B—C25—H25C	109.5
C10—C9—C8	109.3 (3)	C10—C26—H26A	109.5
C10—C9—C4	119.5 (4)	C10—C26—H26B	109.5
C8—C9—C4	111.3 (3)	H26A—C26—H26B	109.5
C10—C9—H9A	105.1	C10—C26—H26C	109.5
C8—C9—H9A	105.1	H26A—C26—H26C	109.5
C4—C9—H9A	105.1	H26B—C26—H26C	109.5
O1—C10—C27	109.3 (4)	C10—C27—H27A	109.5
O1—C10—C26	99.0 (3)	C10—C27—H27C	109.5
C27—C10—C26	108.5 (4)	H27A—C27—H27C	109.5
O1—C10—C9	108.9 (3)	C10—C27—H27D	109.5
C27—C10—C9	117.9 (4)	H27A—C27—H27D	109.5
C26—C10—C9	111.5 (4)	H27C—C27—H27D	109.5
C12—C11—C5	109.2 (3)	C13—C28—H28C	109.5
C12—C11—H11A	109.8	C13—C28—H28D	109.5
C5—C11—H11A	109.8	H28C—C28—H28D	109.5
C12—C11—H11B	109.8	C13—C28—H28A	109.5
C5—C11—H11B	109.8	H28C—C28—H28A	109.5
H11A—C11—H11B	108.3	H28D—C28—H28A	109.5
C11—C12—C13	114.0 (3)	Cl2'—C29—Cl3'	114.8 (8)
C11—C12—H12A	108.7	Cl2'—C29—Cl1'	115.5 (9)
C13—C12—H12A	108.7	Cl3'—C29—Cl1'	115.8 (8)
C11—C12—H12B	108.7	Cl2'—C29—Cl3	135.1 (8)
C13—C12—H12B	108.7	Cl3'—C29—Cl3	22.8 (6)
H12A—C12—H12B	107.6	Cl1'—C29—Cl3	94.0 (8)
C14—C13—C28	109.7 (3)	Cl2'—C29—Cl1	97.4 (8)
C14—C13—C12	108.1 (3)	Cl3'—C29—Cl1	131.1 (7)
C28—C13—C12	114.1 (4)	Cl1'—C29—Cl1	18.4 (9)
C14—C13—C17	108.0 (3)	Cl3—C29—Cl1	110.7 (6)
C28—C13—C17	108.6 (4)	Cl2'—C29—Cl2	27.9 (6)
C12—C13—C17	108.1 (3)	Cl3'—C29—Cl2	90.5 (8)
O6—C14—C15	58.4 (3)	Cl1'—C29—Cl2	120.4 (9)
O6—C14—C13	111.7 (3)	Cl3—C29—Cl2	108.3 (5)
C15—C14—C13	116.9 (4)	Cl1—C29—Cl2	106.1 (6)
O6—C14—C6	114.7 (3)	Cl2'—C29—H29	90.0
C15—C14—C6	119.8 (3)	Cl3'—C29—H29	105.6
C13—C14—C6	119.4 (3)	Cl1'—C29—H29	111.7
O6—C15—C14	59.8 (3)	Cl3—C29—H29	110.5
O6—C15—C16	116.6 (4)	Cl1—C29—H29	110.5
C14—C15—C16	118.8 (4)	Cl2—C29—H29	110.5
O6—C15—H15A	116.5
C10—O1—C1—O2	−171.9 (4)	C11—C12—C13—C28	100.3 (4)
C10—O1—C1—C2	8.1 (7)	C11—C12—C13—C17	−138.7 (4)
O2—C1—C2—C3	−124.3 (5)	C15—O6—C14—C13	−109.1 (4)
O1—C1—C2—C3	55.8 (6)	C15—O6—C14—C6	111.0 (4)
C22—O3—C3—C2	89.3 (4)	C28—C13—C14—O6	151.1 (4)
C22—O3—C3—C4	−141.3 (4)	C12—C13—C14—O6	−83.8 (4)
C1—C2—C3—O3	48.8 (5)	C17—C13—C14—O6	32.9 (5)
C1—C2—C3—C4	−74.5 (5)	C28—C13—C14—C15	86.6 (4)
O3—C3—C4—C24	169.3 (3)	C12—C13—C14—C15	−148.4 (4)
C2—C3—C4—C24	−68.2 (4)	C17—C13—C14—C15	−31.6 (5)
O3—C3—C4—C5	50.1 (4)	C28—C13—C14—C6	−71.1 (5)
C2—C3—C4—C5	172.6 (4)	C12—C13—C14—C6	54.0 (5)
O3—C3—C4—C9	−63.8 (4)	C17—C13—C14—C6	170.7 (4)
C2—C3—C4—C9	58.7 (5)	C7—C6—C14—O6	−127.2 (4)
C3—C4—C5—C11	51.1 (4)	C25—C6—C14—O6	−8.2 (5)
C24—C4—C5—C11	−64.3 (4)	C5—C6—C14—O6	117.4 (4)
C9—C4—C5—C11	168.8 (3)	C7—C6—C14—C15	−60.8 (5)
C3—C4—C5—C6	−178.1 (3)	C25—C6—C14—C15	58.1 (5)
C24—C4—C5—C6	66.5 (4)	C5—C6—C14—C15	−176.2 (3)
C9—C4—C5—C6	−60.4 (4)	C7—C6—C14—C13	96.2 (4)
C11—C5—C6—C7	−164.6 (3)	C25—C6—C14—C13	−144.8 (4)
C4—C5—C6—C7	59.0 (4)	C5—C6—C14—C13	−19.2 (5)
C11—C5—C6—C25	77.3 (4)	C14—O6—C15—C16	109.3 (4)
C4—C5—C6—C25	−59.1 (5)	C13—C14—C15—O6	100.1 (4)
C11—C5—C6—C14	−43.7 (4)	C6—C14—C15—O6	−102.3 (4)
C4—C5—C6—C14	179.9 (3)	O6—C14—C15—C16	−105.8 (4)
C25—C6—C7—O5	−110.5 (5)	C13—C14—C15—C16	−5.7 (5)
C14—C6—C7—O5	8.8 (6)	C6—C14—C15—C16	151.9 (4)
C5—C6—C7—O5	126.0 (5)	C17—O7—C16—O8	−178.9 (4)
C25—C6—C7—C8	70.6 (4)	C17—O7—C16—C15	0.3 (6)
C14—C6—C7—C8	−170.1 (3)	O6—C15—C16—O8	135.0 (4)
C5—C6—C7—C8	−53.0 (4)	C14—C15—C16—O8	−156.5 (4)
O5—C7—C8—C9	−124.5 (5)	O6—C15—C16—O7	−44.2 (6)
C6—C7—C8—C9	54.5 (5)	C14—C15—C16—O7	24.3 (6)
C7—C8—C9—C10	172.1 (4)	C16—O7—C17—C18	−165.1 (4)
C7—C8—C9—C4	−53.7 (5)	C16—O7—C17—C13	−41.0 (5)
C3—C4—C9—C10	−62.6 (4)	C14—C13—C17—O7	54.4 (4)
C24—C4—C9—C10	58.3 (5)	C28—C13—C17—O7	−64.5 (4)
C5—C4—C9—C10	−177.7 (3)	C12—C13—C17—O7	171.2 (3)
C3—C4—C9—C8	168.4 (3)	C14—C13—C17—C18	173.3 (4)
C24—C4—C9—C8	−70.7 (4)	C28—C13—C17—C18	54.5 (5)
C5—C4—C9—C8	53.2 (4)	C12—C13—C17—C18	−69.9 (5)
C1—O1—C10—C27	65.8 (5)	O7—C17—C18—C19	5.5 (7)
C1—O1—C10—C26	179.1 (4)	C13—C17—C18—C19	−117.6 (6)
C1—O1—C10—C9	−64.4 (6)	O7—C17—C18—C21	−174.0 (5)
C8—C9—C10—O1	−152.5 (4)	C13—C17—C18—C21	62.9 (7)
C4—C9—C10—O1	77.6 (5)	C21—C18—C19—O9	−0.1 (7)
C8—C9—C10—C27	82.2 (5)	C17—C18—C19—O9	−179.7 (5)
C4—C9—C10—C27	−47.7 (5)	C20—O9—C19—C18	−0.3 (8)
C8—C9—C10—C26	−44.3 (5)	C19—O9—C20—C21	0.6 (8)
C4—C9—C10—C26	−174.2 (4)	O9—C20—C21—C18	−0.7 (7)
C4—C5—C11—C12	−149.7 (4)	C19—C18—C21—C20	0.5 (7)
C6—C5—C11—C12	75.1 (4)	C17—C18—C21—C20	−179.9 (5)
C5—C11—C12—C13	−38.3 (5)	C3—O3—C22—O4	−2.4 (7)
C11—C12—C13—C14	−22.0 (5)	C3—O3—C22—C23	175.0 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C24—H24C···O5^i	0.96	2.76	3.657 (6)	155
C11—H11B···O8^i	0.97	2.67	3.274 (6)	120
C20—H20A···O2^ii	0.93	2.57	3.489 (8)	168
C17—H17A···O8^iii	0.98	2.59	3.374 (6)	137

Symmetry codes: (i) x−1, y, z; (ii) x+1/2, −y+1/2, −z+1; (iii) x−1/2, −y+3/2, −z+1.