8,13-Diisopropyl-10,11-dimethyl-bis([1,3]dioxolo[4′,5′:6,7]naphtho)­[1,2-d;2,1-f][1,3]dioxepine

The title compound, C₃₁H₃₀O₆, was obtained by protecting the six hy­droxy groups of apogossypol by acetalization with di­chloro­methane. The mol­ecule has a bridging dioxepine unit which hinders the rotation around the 2,2′-inter­naphthyl bond. The dihedral angle between the naphthyl units is 55.73 (3)°. In the crystal, very weak C—H...O inter­actions may help to consolidate the packing.

Key indicators

• Single-crystal X-ray study
• T = 150 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.045
• wR factor = 0.138
• Data-to-parameter ratio = 17.4

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       2.12 Report
PLAT410_ALERT_2_C Short Intra H...H Contact  H4       ..H25      .       1.97 Ang.
                                                      x,y,z  =      1_555 Check
PLAT410_ALERT_2_C Short Intra H...H Contact  H14      ..H29      .       1.99 Ang.
                                                      x,y,z  =      1_555 Check
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.600          2 Report

Alert level G
PLAT154_ALERT_1_G The s.u.'s on the Cell Angles are Equal ..(Note)     0.0016 Degree
PLAT398_ALERT_2_G Deviating  C-O-C    Angle From 120 for O1             105.2 Degree
PLAT398_ALERT_2_G Deviating  C-O-C    Angle From 120 for O2             104.4 Degree
PLAT398_ALERT_2_G Deviating  C-O-C    Angle From 120 for O5             105.2 Degree
PLAT398_ALERT_2_G Deviating  C-O-C    Angle From 120 for O6             106.0 Degree
PLAT933_ALERT_2_G Number of OMIT Records in Embedded .res File ...          2 Note
PLAT960_ALERT_3_G Number of Intensities with I  <   - 2*sig(I) ...          2 Check
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.         20 Info

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   4 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   8 ALERT level G = General information/check it is not something unexpected

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   9 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

---

Computing details

Data collection: APEX2 (Bruker, 2014); cell refinement: SAINT (Bruker, 2013); data reduction: SAINT (Bruker, 2013); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014/7 (Sheldrick, 2015); molecular graphics: XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: publCIF (Westrip, 2010).

8,13-Diisopropyl-10,11-dimethyl-bis([1,3]dioxolo[4',5':6,7]naphtho)[1,2-d;2,1-f][1,3]dioxepine

Crystal data

C31H30O6	Z = 2
Mr = 498.55	F(000) = 528
Triclinic, P1	Dx = 1.350 Mg m^−3
a = 9.7053 (6) Å	Mo Kα radiation, λ = 0.71073 Å
b = 11.0901 (7) Å	Cell parameters from 9929 reflections
c = 12.4156 (8) Å	θ = 2.8–30.6°
α = 68.0282 (16)°	µ = 0.09 mm^−1
β = 81.7012 (16)°	T = 150 K
γ = 86.4672 (16)°	Part of a plate, orange
V = 1226.25 (13) Å^3	0.46 × 0.33 × 0.18 mm

Data collection

Bruker APEXII CCD diffractometer	5923 independent reflections
Radiation source: fine-focus sealed tube	4941 reflections with I > 2σ(I)
Detector resolution: 8.3333 pixels mm^-1	Rint = 0.023
φ and ω scans	θmax = 28.0°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2014)	h = −12→12
Tmin = 0.95, Tmax = 0.98	k = −14→14
43308 measured reflections	l = −16→16

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.045	H-atom parameters constrained
wR(F^2) = 0.138	w = 1/[σ^2(Fo^2) + (0.0747P)^2 + 0.4119P] where P = (Fo^2 + 2Fc^2)/3
S = 1.05	(Δ/σ)max < 0.001
5923 reflections	Δρmax = 0.50 e Å^−3
340 parameters	Δρmin = −0.24 e Å^−3
0 restraints

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. All H atoms were placed in idealized positions with d(C—H) = 0.95–1.00 Å (CH), 0.99 (CH₂), 0.98 Å (CH₃) and refined using a riding model with U_iso(H) fixed at 1.2 U_eq(C) for CH, CH₂ and 1.5 U_eq(C) for CH₃.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
C1	0.82699 (13)	0.25631 (12)	0.23443 (11)	0.0250 (3)
C2	0.76549 (13)	0.22345 (11)	0.34917 (11)	0.0241 (2)
C3	0.61762 (13)	0.21611 (12)	0.37149 (11)	0.0261 (3)
C4	0.54302 (13)	0.23621 (12)	0.27978 (11)	0.0264 (3)
H4	0.4443	0.2325	0.2958	0.032*
C5	0.60517 (13)	0.26203 (12)	0.16310 (11)	0.0252 (3)
C6	0.52512 (14)	0.27466 (12)	0.06984 (12)	0.0279 (3)
C7	0.60147 (14)	0.29242 (13)	−0.03592 (12)	0.0310 (3)
C8	0.74758 (15)	0.30407 (14)	−0.05803 (12)	0.0316 (3)
C9	0.82598 (14)	0.29600 (13)	0.02588 (11)	0.0288 (3)
H9	0.9243	0.3051	0.0098	0.035*
C10	0.75335 (13)	0.27314 (11)	0.13981 (11)	0.0248 (3)
C11	0.94951 (13)	0.31227 (12)	0.41291 (11)	0.0241 (2)
C12	0.85840 (13)	0.21138 (12)	0.43837 (11)	0.0240 (2)
C13	0.86743 (13)	0.10115 (12)	0.54305 (11)	0.0258 (3)
C14	0.96098 (14)	0.10164 (12)	0.61658 (11)	0.0272 (3)
H14	0.9651	0.0277	0.6866	0.033*
C15	1.05123 (13)	0.20650 (12)	0.59326 (11)	0.0249 (3)
C16	1.14992 (14)	0.20510 (12)	0.67065 (11)	0.0265 (3)
C17	1.22813 (13)	0.31411 (12)	0.63546 (11)	0.0266 (3)
C18	1.22056 (13)	0.42122 (12)	0.53020 (12)	0.0261 (3)
C19	1.13326 (13)	0.42565 (12)	0.45361 (11)	0.0265 (3)
H19	1.1302	0.4978	0.3821	0.032*
C20	1.04574 (13)	0.31570 (12)	0.48625 (11)	0.0239 (2)
C21	0.67417 (17)	0.2882 (2)	−0.21373 (14)	0.0475 (4)
H21A	0.6668	0.3455	−0.2959	0.057*
H21B	0.6843	0.1971	−0.2094	0.057*
C22	1.01188 (14)	0.39371 (14)	0.21042 (12)	0.0324 (3)
H22A	1.1140	0.3928	0.2104	0.039*
H22B	0.9894	0.4647	0.1381	0.039*
C23	1.36283 (15)	0.47149 (13)	0.63326 (13)	0.0329 (3)
H23A	1.4647	0.4831	0.6241	0.039*
H23B	1.3167	0.5232	0.6784	0.039*
C24	0.53967 (15)	0.19488 (15)	0.49121 (12)	0.0334 (3)
H24A	0.4524	0.2450	0.4830	0.050*
H24B	0.5969	0.2237	0.5358	0.050*
H24C	0.5190	0.1022	0.5326	0.050*
C25	0.36832 (14)	0.25869 (15)	0.08976 (13)	0.0337 (3)
H25	0.3333	0.2680	0.1661	0.040*
C26	0.33202 (18)	0.12209 (17)	0.10137 (15)	0.0454 (4)
H26A	0.3637	0.1103	0.0273	0.068*
H26B	0.2310	0.1104	0.1201	0.068*
H26C	0.3781	0.0578	0.1641	0.068*
C27	0.29569 (16)	0.36318 (17)	−0.00509 (15)	0.0431 (4)
H27A	0.3218	0.4495	−0.0107	0.065*
H27B	0.1946	0.3532	0.0152	0.065*
H27C	0.3242	0.3538	−0.0806	0.065*
C28	0.78370 (15)	−0.01978 (13)	0.57202 (12)	0.0321 (3)
H28A	0.8394	−0.0967	0.6103	0.048*
H28B	0.7583	−0.0236	0.4998	0.048*
H28C	0.6990	−0.0176	0.6248	0.048*
C29	1.16247 (16)	0.09451 (13)	0.78629 (12)	0.0340 (3)
H29	1.1097	0.0188	0.7884	0.041*
C30	1.31337 (18)	0.05092 (15)	0.80179 (14)	0.0426 (4)
H30A	1.3551	0.0262	0.7362	0.064*
H30B	1.3154	−0.0238	0.8755	0.064*
H30C	1.3662	0.1225	0.8036	0.064*
C31	1.09481 (18)	0.13534 (19)	0.88678 (14)	0.0481 (4)
H31A	1.1403	0.2137	0.8828	0.072*
H31B	1.1052	0.0649	0.9618	0.072*
H31C	0.9956	0.1535	0.8801	0.072*
O1	0.55313 (11)	0.30220 (11)	−0.13812 (9)	0.0404 (3)
O2	0.79134 (11)	0.32419 (12)	−0.17393 (9)	0.0414 (3)
O3	0.97105 (9)	0.27298 (9)	0.20978 (8)	0.0295 (2)
O4	0.94521 (9)	0.41888 (8)	0.30849 (8)	0.0278 (2)
O5	1.31535 (10)	0.51336 (9)	0.52047 (9)	0.0330 (2)
O6	1.32875 (11)	0.33807 (9)	0.69250 (9)	0.0336 (2)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0229 (6)	0.0248 (6)	0.0275 (6)	−0.0008 (4)	−0.0039 (5)	−0.0095 (5)
C2	0.0255 (6)	0.0221 (5)	0.0258 (6)	−0.0024 (4)	−0.0046 (5)	−0.0093 (5)
C3	0.0274 (6)	0.0243 (6)	0.0270 (6)	−0.0044 (5)	−0.0015 (5)	−0.0101 (5)
C4	0.0234 (6)	0.0253 (6)	0.0307 (6)	−0.0034 (4)	−0.0024 (5)	−0.0105 (5)
C5	0.0265 (6)	0.0211 (5)	0.0282 (6)	−0.0013 (4)	−0.0060 (5)	−0.0083 (5)
C6	0.0270 (6)	0.0266 (6)	0.0297 (6)	−0.0006 (5)	−0.0073 (5)	−0.0085 (5)
C7	0.0325 (7)	0.0320 (7)	0.0276 (6)	−0.0011 (5)	−0.0107 (5)	−0.0075 (5)
C8	0.0332 (7)	0.0347 (7)	0.0230 (6)	−0.0018 (5)	−0.0028 (5)	−0.0064 (5)
C9	0.0256 (6)	0.0318 (6)	0.0266 (6)	−0.0018 (5)	−0.0038 (5)	−0.0077 (5)
C10	0.0259 (6)	0.0218 (6)	0.0256 (6)	−0.0004 (4)	−0.0048 (5)	−0.0071 (5)
C11	0.0258 (6)	0.0220 (6)	0.0233 (6)	0.0000 (4)	−0.0036 (5)	−0.0070 (5)
C12	0.0248 (6)	0.0248 (6)	0.0235 (6)	−0.0021 (4)	−0.0026 (4)	−0.0101 (5)
C13	0.0293 (6)	0.0235 (6)	0.0246 (6)	−0.0047 (5)	−0.0018 (5)	−0.0087 (5)
C14	0.0340 (7)	0.0235 (6)	0.0228 (6)	−0.0031 (5)	−0.0045 (5)	−0.0064 (5)
C15	0.0291 (6)	0.0230 (6)	0.0244 (6)	−0.0005 (5)	−0.0048 (5)	−0.0103 (5)
C16	0.0326 (6)	0.0231 (6)	0.0253 (6)	0.0002 (5)	−0.0072 (5)	−0.0094 (5)
C17	0.0284 (6)	0.0261 (6)	0.0285 (6)	0.0014 (5)	−0.0081 (5)	−0.0124 (5)
C18	0.0234 (6)	0.0229 (6)	0.0321 (6)	−0.0027 (4)	−0.0029 (5)	−0.0103 (5)
C19	0.0261 (6)	0.0232 (6)	0.0277 (6)	−0.0021 (5)	−0.0036 (5)	−0.0063 (5)
C20	0.0250 (6)	0.0220 (5)	0.0251 (6)	−0.0010 (4)	−0.0035 (5)	−0.0092 (5)
C21	0.0429 (9)	0.0684 (11)	0.0304 (8)	−0.0067 (8)	−0.0077 (6)	−0.0152 (7)
C22	0.0289 (6)	0.0376 (7)	0.0272 (6)	−0.0094 (5)	−0.0025 (5)	−0.0071 (5)
C23	0.0303 (7)	0.0305 (7)	0.0386 (7)	−0.0030 (5)	−0.0112 (6)	−0.0107 (6)
C24	0.0296 (6)	0.0419 (8)	0.0298 (7)	−0.0062 (6)	0.0008 (5)	−0.0154 (6)
C25	0.0267 (6)	0.0435 (8)	0.0318 (7)	−0.0026 (5)	−0.0069 (5)	−0.0134 (6)
C26	0.0417 (8)	0.0469 (9)	0.0433 (9)	−0.0145 (7)	−0.0093 (7)	−0.0085 (7)
C27	0.0325 (7)	0.0484 (9)	0.0479 (9)	0.0061 (6)	−0.0130 (6)	−0.0153 (7)
C28	0.0381 (7)	0.0271 (6)	0.0305 (7)	−0.0085 (5)	−0.0056 (5)	−0.0081 (5)
C29	0.0433 (8)	0.0274 (6)	0.0305 (7)	−0.0062 (6)	−0.0142 (6)	−0.0056 (5)
C30	0.0509 (9)	0.0321 (7)	0.0402 (8)	0.0095 (6)	−0.0125 (7)	−0.0073 (6)
C31	0.0428 (9)	0.0621 (11)	0.0313 (8)	−0.0035 (8)	−0.0034 (6)	−0.0082 (7)
O1	0.0369 (5)	0.0571 (7)	0.0278 (5)	−0.0021 (5)	−0.0118 (4)	−0.0135 (5)
O2	0.0380 (6)	0.0606 (7)	0.0227 (5)	−0.0051 (5)	−0.0055 (4)	−0.0106 (5)
O3	0.0223 (4)	0.0379 (5)	0.0281 (5)	−0.0021 (4)	−0.0028 (3)	−0.0119 (4)
O4	0.0289 (5)	0.0245 (4)	0.0261 (5)	−0.0035 (3)	−0.0055 (4)	−0.0037 (4)
O5	0.0303 (5)	0.0294 (5)	0.0379 (5)	−0.0079 (4)	−0.0102 (4)	−0.0075 (4)
O6	0.0378 (5)	0.0282 (5)	0.0381 (5)	−0.0032 (4)	−0.0166 (4)	−0.0114 (4)

Geometric parameters (Å, º)

C1—C2	1.3825 (18)	C21—O1	1.433 (2)
C1—O3	1.3959 (15)	C21—O2	1.4362 (19)
C1—C10	1.4098 (17)	C21—H21A	0.9900
C2—C3	1.4233 (17)	C21—H21B	0.9900
C2—C12	1.4900 (16)	C22—O4	1.4085 (17)
C3—C4	1.3779 (17)	C22—O3	1.4226 (17)
C3—C24	1.5075 (18)	C22—H22A	0.9900
C4—C5	1.4152 (18)	C22—H22B	0.9900
C4—H4	0.9500	C23—O6	1.4197 (17)
C5—C10	1.4290 (17)	C23—O5	1.4362 (17)
C5—C6	1.4453 (17)	C23—H23A	0.9900
C6—C7	1.362 (2)	C23—H23B	0.9900
C6—C25	1.5167 (18)	C24—H24A	0.9800
C7—O1	1.3801 (16)	C24—H24B	0.9800
C7—C8	1.4094 (19)	C24—H24C	0.9800
C8—C9	1.3502 (18)	C25—C26	1.526 (2)
C8—O2	1.3769 (16)	C25—C27	1.531 (2)
C9—C10	1.4241 (18)	C25—H25	1.0000
C9—H9	0.9500	C26—H26A	0.9800
C11—C12	1.3821 (17)	C26—H26B	0.9800
C11—O4	1.3939 (14)	C26—H26C	0.9800
C11—C20	1.4066 (17)	C27—H27A	0.9800
C12—C13	1.4219 (17)	C27—H27B	0.9800
C13—C14	1.3789 (17)	C27—H27C	0.9800
C13—C28	1.5091 (17)	C28—H28A	0.9800
C14—C15	1.4155 (17)	C28—H28B	0.9800
C14—H14	0.9500	C28—H28C	0.9800
C15—C20	1.4293 (17)	C29—C30	1.530 (2)
C15—C16	1.4470 (17)	C29—C31	1.530 (2)
C16—C17	1.3604 (18)	C29—H29	1.0000
C16—C29	1.5149 (18)	C30—H30A	0.9800
C17—O6	1.3777 (15)	C30—H30B	0.9800
C17—C18	1.4070 (18)	C30—H30C	0.9800
C18—C19	1.3479 (18)	C31—H31A	0.9800
C18—O5	1.3771 (15)	C31—H31B	0.9800
C19—C20	1.4252 (17)	C31—H31C	0.9800
C19—H19	0.9500
C2—C1—O3	118.53 (11)	O4—C22—O3	112.29 (10)
C2—C1—C10	124.07 (11)	O4—C22—H22A	109.1
O3—C1—C10	117.40 (11)	O3—C22—H22A	109.1
C1—C2—C3	117.75 (11)	O4—C22—H22B	109.1
C1—C2—C12	117.17 (11)	O3—C22—H22B	109.1
C3—C2—C12	124.79 (11)	H22A—C22—H22B	107.9
C4—C3—C2	119.11 (11)	O6—C23—O5	107.43 (10)
C4—C3—C24	118.90 (12)	O6—C23—H23A	110.2
C2—C3—C24	121.90 (11)	O5—C23—H23A	110.2
C3—C4—C5	123.69 (12)	O6—C23—H23B	110.2
C3—C4—H4	118.2	O5—C23—H23B	110.2
C5—C4—H4	118.2	H23A—C23—H23B	108.5
C4—C5—C10	117.31 (11)	C3—C24—H24A	109.5
C4—C5—C6	122.60 (12)	C3—C24—H24B	109.5
C10—C5—C6	120.08 (12)	H24A—C24—H24B	109.5
C7—C6—C5	115.21 (12)	C3—C24—H24C	109.5
C7—C6—C25	121.96 (12)	H24A—C24—H24C	109.5
C5—C6—C25	122.65 (12)	H24B—C24—H24C	109.5
C6—C7—O1	127.54 (13)	C6—C25—C26	110.01 (12)
C6—C7—C8	124.16 (12)	C6—C25—C27	112.64 (12)
O1—C7—C8	108.30 (12)	C26—C25—C27	111.63 (12)
C9—C8—O2	128.09 (13)	C6—C25—H25	107.4
C9—C8—C7	122.49 (12)	C26—C25—H25	107.4
O2—C8—C7	109.42 (12)	C27—C25—H25	107.4
C8—C9—C10	116.41 (12)	C25—C26—H26A	109.5
C8—C9—H9	121.8	C25—C26—H26B	109.5
C10—C9—H9	121.8	H26A—C26—H26B	109.5
C1—C10—C9	120.48 (11)	C25—C26—H26C	109.5
C1—C10—C5	117.89 (11)	H26A—C26—H26C	109.5
C9—C10—C5	121.59 (11)	H26B—C26—H26C	109.5
C12—C11—O4	118.23 (11)	C25—C27—H27A	109.5
C12—C11—C20	124.36 (11)	C25—C27—H27B	109.5
O4—C11—C20	117.41 (10)	H27A—C27—H27B	109.5
C11—C12—C13	117.62 (11)	C25—C27—H27C	109.5
C11—C12—C2	116.91 (11)	H27A—C27—H27C	109.5
C13—C12—C2	125.32 (11)	H27B—C27—H27C	109.5
C14—C13—C12	119.25 (11)	C13—C28—H28A	109.5
C14—C13—C28	119.01 (11)	C13—C28—H28B	109.5
C12—C13—C28	121.62 (11)	H28A—C28—H28B	109.5
C13—C14—C15	123.47 (11)	C13—C28—H28C	109.5
C13—C14—H14	118.3	H28A—C28—H28C	109.5
C15—C14—H14	118.3	H28B—C28—H28C	109.5
C14—C15—C20	117.46 (11)	C16—C29—C30	112.64 (12)
C14—C15—C16	122.87 (11)	C16—C29—C31	109.28 (12)
C20—C15—C16	119.64 (11)	C30—C29—C31	110.71 (12)
C17—C16—C15	115.30 (11)	C16—C29—H29	108.0
C17—C16—C29	121.16 (11)	C30—C29—H29	108.0
C15—C16—C29	123.47 (11)	C31—C29—H29	108.0
C16—C17—O6	127.12 (12)	C29—C30—H30A	109.5
C16—C17—C18	124.26 (12)	C29—C30—H30B	109.5
O6—C17—C18	108.60 (11)	H30A—C30—H30B	109.5
C19—C18—O5	127.98 (12)	C29—C30—H30C	109.5
C19—C18—C17	122.69 (11)	H30A—C30—H30C	109.5
O5—C18—C17	109.32 (11)	H30B—C30—H30C	109.5
C18—C19—C20	116.05 (11)	C29—C31—H31A	109.5
C18—C19—H19	122.0	C29—C31—H31B	109.5
C20—C19—H19	122.0	H31A—C31—H31B	109.5
C11—C20—C19	120.23 (11)	C29—C31—H31C	109.5
C11—C20—C15	117.76 (11)	H31A—C31—H31C	109.5
C19—C20—C15	122.01 (11)	H31B—C31—H31C	109.5
O1—C21—O2	106.62 (12)	C7—O1—C21	105.23 (11)
O1—C21—H21A	110.4	C8—O2—C21	104.42 (11)
O2—C21—H21A	110.4	C1—O3—C22	112.20 (10)
O1—C21—H21B	110.4	C11—O4—C22	112.54 (10)
O2—C21—H21B	110.4	C18—O5—C23	105.17 (10)
H21A—C21—H21B	108.6	C17—O6—C23	106.00 (10)
O3—C1—C2—C3	175.54 (10)	C13—C14—C15—C16	−179.34 (12)
C10—C1—C2—C3	−5.07 (19)	C14—C15—C16—C17	−179.62 (12)
O3—C1—C2—C12	1.47 (17)	C20—C15—C16—C17	2.43 (18)
C10—C1—C2—C12	−179.13 (11)	C14—C15—C16—C29	−2.7 (2)
C1—C2—C3—C4	2.77 (18)	C20—C15—C16—C29	179.38 (12)
C12—C2—C3—C4	176.34 (11)	C15—C16—C17—O6	179.85 (12)
C1—C2—C3—C24	−173.52 (12)	C29—C16—C17—O6	2.8 (2)
C12—C2—C3—C24	0.05 (19)	C15—C16—C17—C18	−2.0 (2)
C2—C3—C4—C5	1.10 (19)	C29—C16—C17—C18	−179.06 (12)
C24—C3—C4—C5	177.50 (12)	C16—C17—C18—C19	0.2 (2)
C3—C4—C5—C10	−2.82 (18)	O6—C17—C18—C19	178.63 (12)
C3—C4—C5—C6	176.00 (12)	C16—C17—C18—O5	−178.74 (12)
C4—C5—C6—C7	−176.55 (12)	O6—C17—C18—O5	−0.33 (15)
C10—C5—C6—C7	2.23 (18)	O5—C18—C19—C20	179.94 (12)
C4—C5—C6—C25	−1.22 (19)	C17—C18—C19—C20	1.19 (19)
C10—C5—C6—C25	177.56 (12)	C12—C11—C20—C19	−178.50 (12)
C5—C6—C7—O1	177.26 (12)	O4—C11—C20—C19	0.63 (17)
C25—C6—C7—O1	1.9 (2)	C12—C11—C20—C15	1.13 (19)
C5—C6—C7—C8	−2.8 (2)	O4—C11—C20—C15	−179.73 (11)
C25—C6—C7—C8	−178.14 (13)	C18—C19—C20—C11	178.95 (12)
C6—C7—C8—C9	1.3 (2)	C18—C19—C20—C15	−0.67 (18)
O1—C7—C8—C9	−178.72 (13)	C14—C15—C20—C11	1.14 (18)
C6—C7—C8—O2	−178.55 (13)	C16—C15—C20—C11	179.20 (11)
O1—C7—C8—O2	1.42 (16)	C14—C15—C20—C19	−179.23 (11)
O2—C8—C9—C10	−179.36 (13)	C16—C15—C20—C19	−1.18 (19)
C7—C8—C9—C10	0.8 (2)	C7—C6—C25—C26	76.33 (16)
C2—C1—C10—C9	−174.57 (12)	C5—C6—C25—C26	−98.68 (15)
O3—C1—C10—C9	4.83 (17)	C7—C6—C25—C27	−48.91 (18)
C2—C1—C10—C5	3.33 (19)	C5—C6—C25—C27	136.07 (14)
O3—C1—C10—C5	−177.27 (10)	C17—C16—C29—C30	−50.79 (18)
C8—C9—C10—C1	176.59 (12)	C15—C16—C29—C30	132.44 (14)
C8—C9—C10—C5	−1.23 (19)	C17—C16—C29—C31	72.70 (17)
C4—C5—C10—C1	0.65 (17)	C15—C16—C29—C31	−104.07 (15)
C6—C5—C10—C1	−178.19 (11)	C6—C7—O1—C21	−166.34 (15)
C4—C5—C10—C9	178.53 (11)	C8—C7—O1—C21	13.69 (16)
C6—C5—C10—C9	−0.31 (18)	O2—C21—O1—C7	−23.43 (17)
O4—C11—C12—C13	177.72 (11)	C9—C8—O2—C21	164.34 (16)
C20—C11—C12—C13	−3.15 (19)	C7—C8—O2—C21	−15.81 (16)
O4—C11—C12—C2	1.94 (17)	O1—C21—O2—C8	24.11 (17)
C20—C11—C12—C2	−178.93 (11)	C2—C1—O3—C22	−76.37 (14)
C1—C2—C12—C11	49.07 (16)	C10—C1—O3—C22	104.20 (12)
C3—C2—C12—C11	−124.53 (13)	O4—C22—O3—C1	46.28 (14)
C1—C2—C12—C13	−126.35 (13)	C12—C11—O4—C22	−77.59 (14)
C3—C2—C12—C13	60.04 (18)	C20—C11—O4—C22	103.22 (13)
C11—C12—C13—C14	2.84 (18)	O3—C22—O4—C11	47.28 (14)
C2—C12—C13—C14	178.23 (12)	C19—C18—O5—C23	170.18 (13)
C11—C12—C13—C28	−173.25 (12)	C17—C18—O5—C23	−10.94 (14)
C2—C12—C13—C28	2.1 (2)	O6—C23—O5—C18	18.06 (14)
C12—C13—C14—C15	−0.7 (2)	C16—C17—O6—C23	−170.02 (14)
C28—C13—C14—C15	175.52 (12)	C18—C17—O6—C23	11.63 (14)
C13—C14—C15—C20	−1.35 (19)	O5—C23—O6—C17	−18.38 (14)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C23—H23A···O5^i	0.99	2.58	3.3956 (18)	140
C23—H23B···O4^ii	0.99	2.58	3.2442 (18)	124

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