Crystal structure of (±)-(1SR,5SR,6SR,7SR,10SR,11SR,13SR)-13-benz­yloxy-7-meth­oxy­meth­oxy-11,15,18,18-tetra­methyl-3-oxo-2,4-dioxa­tetra­cyclo­[12.3.1.0^1,5.0^6,11]octa­deca-14,16-dien-10-yl benzoate

In the title compound, the ring conformations of the tetra­cycle are twist, chair, half-chair and chair–boat forms. In the crystal, inter­molecular C—H...O and C—H...π inter­actions link mol­ecules to construct a three-dimensional architecture.

Key indicators

• Single-crystal X-ray study
• T = 90 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.047
• wR factor = 0.120
• Data-to-parameter ratio = 13.3

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       2.55 Report
PLAT410_ALERT_2_C Short Intra H...H Contact  H2     ..  H9B     ..       1.98 Ang.
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L=  0.595          4 Report

Alert level G
PLAT005_ALERT_5_G No _iucr_refine_instructions_details  in the CIF     Please Do !
PLAT066_ALERT_1_G Predicted and Reported Tmin&Tmax Range Identical          ? Check
PLAT154_ALERT_1_G The su's on the Cell Angles are Equal ..........    0.00200 Degree
PLAT793_ALERT_4_G The Model has Chirality at C1      (Centro SPGR)          S Verify
PLAT793_ALERT_4_G The Model has Chirality at C2      (Centro SPGR)          S Verify
PLAT793_ALERT_4_G The Model has Chirality at C3      (Centro SPGR)          S Verify
PLAT793_ALERT_4_G The Model has Chirality at C4      (Centro SPGR)          S Verify
PLAT793_ALERT_4_G The Model has Chirality at C7      (Centro SPGR)          S Verify
PLAT793_ALERT_4_G The Model has Chirality at C8      (Centro SPGR)          S Verify
PLAT793_ALERT_4_G The Model has Chirality at C10     (Centro SPGR)          S Verify
PLAT909_ALERT_3_G Percentage of Observed Data at Theta(Max) still          55 %
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Th(Min) ...          3 Report

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

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 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
   7 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check


checkCIF publication errors

Alert level A
PUBL024_ALERT_1_A The number of authors is greater than 5.
              Please specify the role of each of the co-authors
              for your paper.

Author Response: Contributions and roles for this paper are following: Oishi, T.; X-ray analysis and description for the paper. Fukaya, K., Yamaguchi, Y., Sugai, T., Watanabe, A., Sato, T. and Chida, N.; Synthesis (linear 29 and more steps from 3-methylanisole) of the title compound, purification, crystallization and other spectroscopic characterization.

   1 ALERT level A = Data missing that is essential or data in wrong format
   0 ALERT level G = General alerts. Data that may be required is missing

---

Computing details

Data collection: APEX2 (Bruker, 2014); cell refinement: SAINT (Bruker, 2014); data reduction: SAINT (Bruker, 2014); program(s) used to solve structure: SHELXS2013 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: Mercury (Macrae et al., 2006); software used to prepare material for publication: publCIF (Westrip, 2010) and PLATON (Spek, 2009).

(±)-(1SR,5SR,6SR,7SR,10SR,11SR,13SR)-13-Benzyloxy-7-methoxymethoxy-11,15,18,18-tetramethyl-3-oxo-2,4-dioxatetracyclo[12.3.1.0^1,5.0^6,11]octadeca-14,16-dien-10-yl benzoate

Crystal data

C36H42O8	F(000) = 644
Mr = 602.69	Dx = 1.320 Mg m^−3
Triclinic, P1	Melting point: 465.2 K
a = 10.9358 (6) Å	Mo Kα radiation, λ = 0.71073 Å
b = 11.6121 (6) Å	Cell parameters from 9212 reflections
c = 13.6833 (7) Å	θ = 2.2–25.0°
α = 72.148 (2)°	µ = 0.09 mm^−1
β = 86.447 (2)°	T = 90 K
γ = 66.766 (2)°	Prism, colorless
V = 1516.36 (14) Å^3	0.32 × 0.27 × 0.16 mm
Z = 2

Data collection

Bruker D8 Venture diffractometer	5346 independent reflections
Radiation source: fine-focus sealed tube	4078 reflections with I > 2σ(I)
Multilayered confocal mirror monochromator	Rint = 0.052
Detector resolution: 8.333 pixels mm^-1	θmax = 25.0°, θmin = 2.1°
φ and ω scans	h = −13→13
Absorption correction: multi-scan (SADABS; Bruker, 2014)	k = −13→13
Tmin = 0.97, Tmax = 0.98	l = −16→16
27885 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.120	H-atom parameters constrained
S = 1.04	w = 1/[σ^2(Fo^2) + (0.0504P)^2 + 1.0416P] where P = (Fo^2 + 2Fc^2)/3
5346 reflections	(Δ/σ)max = 0.001
402 parameters	Δρmax = 0.59 e Å^−3
0 restraints	Δρmin = −0.23 e Å^−3

Special details

Experimental. M.p. 462.2–465.2 K (not corrected); IR (film): 2940, 1806, 1716, 1274, 1109, 1043, 713 cm^-1; ¹H NMR (500 MHz, CDCl₃): δ (p.p.m.) 8.03 (dd, J = 8.3, 1.2 Hz, 2H), 7.61 (tt, J = 7.5, 1.2 Hz, 1H), 7.49 (ddd, J = 8.3, 7.5, 1.7 Hz, 2H), 7.23–7.12 (m, 5H), 6.17 (d, J = 9.2 Hz, 1H), 5.63 (d, J = 9.2 Hz, 1H), 4.94 (d, J = 4.9 Hz, 1H), 4.90 (dd, J = 11.3, 5.2 Hz, 1H), 4.75 (d, J = 6.9 Hz, 1H), 4.65 (dd, J = 11.7, 5.4 Hz, 1H), 4.50 (d, J = 6.9 Hz, 1H), 4.47 (d, J = 12.0 Hz, 1H), 4.24 (d, J = 12.0 Hz, 1H), 3.70 (ddd, J = 10.5, 10.5, 4.9 Hz, 1H), 3.33 (s, 3H), 2.26 (dddd, J = 13.4, 5.0, 4.9, 2.6 Hz, 1H), 2.12 (dd, J = 15.9, 5.4 Hz, 1H), 2.04 (dd, J = 10.5, 4.9 Hz, 1H), 1.99 (dd, J = 15.9, 11.7 Hz, 1H), 1.91–1.85 (m, 1H), 1.84–1.73 (m, 1H), 1.80 (s, 3H), 1.58 (s, 3H), 1.50 (s, 3H), 1.35–1.24 (m, 1H), 1.18 (s, 3H); ¹³C NMR (125 MHz, CDCl₃): δ (p.p.m.) 165.9 (C), 154.6 (C), 138.3 (C), 138.2 (C), 137.8 (C), 135.5 (CH), 133.5 (CH), 130.6 (CH), 130.1 (C), 129.8 (CH), 128.7 (CH), 128.5 (CH), 127.7 (CH), 127.4 (CH), 97.6 (CH₂), 93.1 (C), 79.7 (CH), 74.2 (CH), 74.1 (CH), 73.4 (CH), 69.9 (CH₂), 56.0 (CH₃), 45.7 (CH), 42.8 (C), 39.8 (CH₂), 37.9 (C), 32.5 (CH₂), 29.5 (CH₃), 25.8 (CH₂), 19.33 (CH₃), 19.27 (CH₃), 17.7 (CH₃); HRMS (ESI): calcd for C₃₆H₄₂O₈Na⁺ [M+Na]⁺ 625.2777, found 625.2777.

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.

Problematic one reflection with |I(obs)-I(calc)|/σW(I) greater than 10 (–2 3 1) has been omitted in the final refinement.

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

	x	y	z	Uiso*/Ueq
C1	0.2090 (2)	0.1750 (2)	0.91158 (15)	0.0210 (5)
C2	0.3204 (2)	0.0817 (2)	0.86310 (15)	0.0198 (5)
H2	0.3938	0.1143	0.8498	0.024*
C3	0.2821 (2)	0.0698 (2)	0.76154 (15)	0.0184 (4)
H3	0.1858	0.1295	0.7447	0.022*
C4	0.2914 (2)	−0.0675 (2)	0.76837 (15)	0.0207 (5)
H4	0.3848	−0.1344	0.7883	0.025*
C5	0.2414 (2)	−0.0651 (2)	0.66551 (15)	0.0225 (5)
H5B	0.2627	−0.1569	0.6672	0.027*
H5A	0.1431	−0.0182	0.6578	0.027*
C6	0.2999 (2)	0.0002 (2)	0.57150 (15)	0.0214 (5)
H6A	0.3951	−0.0565	0.5704	0.026*
H6B	0.2523	0.0104	0.5082	0.026*
C7	0.2877 (2)	0.1337 (2)	0.57361 (15)	0.0191 (5)
H7	0.191	0.191	0.5717	0.023*
C8	0.3583 (2)	0.1246 (2)	0.67110 (15)	0.0183 (4)
C9	0.3595 (2)	0.2595 (2)	0.66630 (16)	0.0199 (5)
H9B	0.4203	0.242	0.7246	0.024*
H9A	0.4028	0.2871	0.6028	0.024*
C10	0.2330 (2)	0.3811 (2)	0.66790 (16)	0.0198 (5)
H10	0.1778	0.413	0.602	0.024*
C11	0.1476 (2)	0.35654 (19)	0.75632 (16)	0.0197 (5)
C12	0.0331 (2)	0.3454 (2)	0.73994 (15)	0.0204 (5)
C13	−0.0137 (2)	0.2618 (2)	0.82427 (16)	0.0230 (5)
H13	−0.1038	0.2705	0.8228	0.028*
C14	0.0722 (2)	0.1738 (2)	0.90249 (16)	0.0229 (5)
H14	0.0479	0.1105	0.9525	0.027*
C15	0.1993 (2)	0.3171 (2)	0.86995 (15)	0.0207 (5)
C16	0.3299 (2)	0.3293 (2)	0.88962 (16)	0.0229 (5)
H16B	0.3555	0.2938	0.9636	0.034*
H16C	0.317	0.4222	0.865	0.034*
H16A	0.4005	0.2795	0.8529	0.034*
C17	0.0958 (2)	0.4076 (2)	0.92429 (16)	0.0243 (5)
H17A	0.0079	0.4077	0.9138	0.036*
H17B	0.092	0.4974	0.8955	0.036*
H17C	0.1216	0.3753	0.9981	0.036*
C18	−0.0437 (2)	0.3934 (2)	0.63817 (16)	0.0255 (5)
H18A	−0.0215	0.4638	0.5908	0.038*
H18B	−0.1396	0.4273	0.648	0.038*
H18C	−0.0202	0.3204	0.6094	0.038*
C19	0.5062 (2)	0.0313 (2)	0.68131 (16)	0.0211 (5)
H19B	0.5135	−0.0561	0.6827	0.032*
H19C	0.5482	0.0244	0.7452	0.032*
H19A	0.5512	0.0659	0.6225	0.032*
O20	0.36857 (14)	−0.04110 (14)	0.94740 (10)	0.0226 (3)
C21	0.3358 (2)	−0.0133 (2)	1.03550 (16)	0.0229 (5)
O22	0.25645 (14)	0.11453 (14)	1.01974 (10)	0.0241 (3)
O23	0.37257 (15)	−0.09211 (15)	1.11907 (11)	0.0301 (4)
O24	0.34533 (13)	0.19559 (14)	0.48470 (10)	0.0200 (3)
C25	0.2682 (2)	0.2569 (2)	0.39610 (15)	0.0204 (5)
O26	0.16003 (15)	0.25445 (15)	0.38570 (11)	0.0290 (4)
C27	0.3292 (2)	0.3303 (2)	0.31322 (15)	0.0192 (4)
C28	0.2699 (2)	0.3799 (2)	0.21389 (16)	0.0269 (5)
H28	0.1964	0.362	0.1999	0.032*
C29	0.3180 (2)	0.4553 (2)	0.13538 (17)	0.0300 (5)
H29	0.2785	0.4879	0.0673	0.036*
C30	0.4233 (2)	0.4832 (2)	0.15603 (17)	0.0299 (5)
H30	0.4553	0.5363	0.1023	0.036*
C31	0.4824 (2)	0.4342 (2)	0.25464 (17)	0.0279 (5)
H31	0.5552	0.4534	0.2684	0.033*
C32	0.4363 (2)	0.3575 (2)	0.33317 (16)	0.0218 (5)
H32	0.4776	0.3234	0.4008	0.026*
O33	0.28434 (14)	0.47725 (14)	0.66845 (11)	0.0239 (3)
C34	0.1863 (2)	0.6092 (2)	0.63828 (16)	0.0246 (5)
H34A	0.1914	0.653	0.6887	0.029*
H34B	0.0964	0.6075	0.6389	0.029*
C35	0.2054 (2)	0.6865 (2)	0.53358 (16)	0.0217 (5)
C36	0.1191 (2)	0.8177 (2)	0.49309 (17)	0.0260 (5)
H36	0.0481	0.8562	0.5317	0.031*
C37	0.1356 (2)	0.8926 (2)	0.39732 (17)	0.0313 (5)
H37	0.0773	0.9827	0.3712	0.038*
C38	0.2363 (2)	0.8373 (3)	0.33917 (18)	0.0346 (6)
H38	0.2465	0.8885	0.2727	0.041*
C39	0.3217 (2)	0.7074 (3)	0.37825 (18)	0.0334 (6)
H39	0.3909	0.6689	0.3383	0.04*
C40	0.3080 (2)	0.6325 (2)	0.47451 (17)	0.0269 (5)
H40	0.3688	0.5433	0.501	0.032*
O41	0.20301 (14)	−0.09407 (14)	0.84612 (10)	0.0234 (3)
C42	0.2292 (2)	−0.2270 (2)	0.89614 (17)	0.0287 (5)
H42B	0.194	−0.2359	0.9653	0.034*
H42A	0.3269	−0.2778	0.9054	0.034*
O43	0.17233 (17)	−0.28080 (15)	0.84205 (12)	0.0328 (4)
C44	0.0307 (2)	−0.2202 (2)	0.83398 (19)	0.0352 (6)
H44C	−0.0029	−0.2401	0.9026	0.053*
H44A	−0.0046	−0.254	0.7899	0.053*
H44B	0.0019	−0.1246	0.8039	0.053*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0266 (11)	0.0233 (12)	0.0175 (11)	−0.0112 (9)	0.0021 (9)	−0.0108 (9)
C2	0.0242 (11)	0.0197 (11)	0.0184 (11)	−0.0102 (9)	0.0022 (9)	−0.0081 (9)
C3	0.0212 (10)	0.0200 (11)	0.0184 (10)	−0.0088 (9)	0.0023 (8)	−0.0110 (9)
C4	0.0234 (11)	0.0212 (12)	0.0221 (11)	−0.0102 (9)	0.0056 (9)	−0.0118 (9)
C5	0.0293 (12)	0.0228 (12)	0.0238 (11)	−0.0148 (10)	0.0043 (9)	−0.0129 (9)
C6	0.0250 (11)	0.0233 (12)	0.0208 (11)	−0.0103 (9)	0.0021 (9)	−0.0124 (9)
C7	0.0210 (11)	0.0224 (11)	0.0182 (11)	−0.0104 (9)	0.0059 (9)	−0.0102 (9)
C8	0.0208 (11)	0.0191 (11)	0.0191 (10)	−0.0086 (9)	0.0026 (8)	−0.0108 (9)
C9	0.0224 (11)	0.0222 (12)	0.0201 (11)	−0.0115 (9)	0.0036 (9)	−0.0102 (9)
C10	0.0230 (11)	0.0192 (11)	0.0232 (11)	−0.0112 (9)	0.0006 (9)	−0.0105 (9)
C11	0.0204 (11)	0.0151 (11)	0.0264 (11)	−0.0057 (9)	0.0014 (9)	−0.0118 (9)
C12	0.0216 (11)	0.0181 (11)	0.0244 (11)	−0.0058 (9)	0.0037 (9)	−0.0137 (9)
C13	0.0203 (11)	0.0268 (12)	0.0281 (12)	−0.0094 (10)	0.0054 (9)	−0.0176 (10)
C14	0.0256 (12)	0.0237 (12)	0.0271 (12)	−0.0122 (10)	0.0105 (10)	−0.0168 (10)
C15	0.0224 (11)	0.0222 (12)	0.0228 (11)	−0.0097 (9)	0.0032 (9)	−0.0132 (9)
C16	0.0272 (12)	0.0264 (12)	0.0225 (11)	−0.0127 (10)	0.0007 (9)	−0.0143 (9)
C17	0.0287 (12)	0.0237 (12)	0.0256 (12)	−0.0107 (10)	0.0043 (9)	−0.0146 (10)
C18	0.0238 (11)	0.0270 (13)	0.0300 (12)	−0.0107 (10)	0.0004 (10)	−0.0136 (10)
C19	0.0236 (11)	0.0244 (12)	0.0206 (11)	−0.0104 (9)	0.0040 (9)	−0.0135 (9)
O20	0.0280 (8)	0.0228 (8)	0.0176 (7)	−0.0086 (7)	0.0013 (6)	−0.0086 (6)
C21	0.0209 (11)	0.0281 (13)	0.0234 (12)	−0.0109 (10)	0.0025 (9)	−0.0115 (10)
O22	0.0316 (8)	0.0251 (9)	0.0187 (8)	−0.0111 (7)	0.0022 (6)	−0.0112 (6)
O23	0.0337 (9)	0.0333 (9)	0.0214 (9)	−0.0122 (7)	−0.0010 (7)	−0.0064 (7)
O24	0.0216 (7)	0.0235 (8)	0.0181 (7)	−0.0104 (6)	0.0018 (6)	−0.0088 (6)
C25	0.0211 (11)	0.0186 (11)	0.0229 (11)	−0.0053 (9)	−0.0003 (9)	−0.0112 (9)
O26	0.0252 (9)	0.0362 (10)	0.0278 (8)	−0.0154 (7)	−0.0016 (7)	−0.0080 (7)
C27	0.0208 (11)	0.0173 (11)	0.0211 (11)	−0.0066 (9)	0.0018 (9)	−0.0095 (9)
C28	0.0292 (12)	0.0304 (13)	0.0271 (12)	−0.0163 (11)	−0.0025 (10)	−0.0098 (10)
C29	0.0380 (14)	0.0318 (14)	0.0219 (12)	−0.0148 (11)	−0.0017 (10)	−0.0084 (10)
C30	0.0365 (13)	0.0330 (13)	0.0246 (12)	−0.0198 (11)	0.0044 (10)	−0.0073 (10)
C31	0.0286 (12)	0.0316 (13)	0.0308 (13)	−0.0171 (11)	0.0036 (10)	−0.0130 (10)
C32	0.0218 (11)	0.0227 (12)	0.0209 (11)	−0.0065 (9)	−0.0013 (9)	−0.0092 (9)
O33	0.0247 (8)	0.0195 (8)	0.0317 (8)	−0.0110 (7)	−0.0002 (6)	−0.0101 (7)
C34	0.0248 (11)	0.0210 (12)	0.0322 (12)	−0.0088 (10)	0.0035 (10)	−0.0146 (10)
C35	0.0232 (11)	0.0249 (12)	0.0252 (11)	−0.0134 (9)	−0.0005 (9)	−0.0131 (9)
C36	0.0247 (12)	0.0270 (13)	0.0317 (13)	−0.0109 (10)	0.0004 (10)	−0.0153 (10)
C37	0.0319 (13)	0.0323 (14)	0.0318 (13)	−0.0165 (11)	−0.0032 (11)	−0.0065 (11)
C38	0.0395 (14)	0.0462 (16)	0.0291 (13)	−0.0300 (13)	0.0020 (11)	−0.0090 (12)
C39	0.0321 (13)	0.0495 (17)	0.0345 (14)	−0.0269 (13)	0.0136 (11)	−0.0221 (12)
C40	0.0232 (12)	0.0292 (13)	0.0371 (13)	−0.0128 (10)	0.0031 (10)	−0.0191 (11)
O41	0.0320 (8)	0.0214 (8)	0.0227 (8)	−0.0143 (7)	0.0076 (6)	−0.0108 (6)
C42	0.0376 (13)	0.0233 (13)	0.0267 (12)	−0.0149 (11)	0.0049 (10)	−0.0063 (10)
O43	0.0443 (10)	0.0288 (9)	0.0386 (9)	−0.0219 (8)	0.0153 (8)	−0.0207 (7)
C44	0.0416 (15)	0.0379 (15)	0.0379 (14)	−0.0252 (12)	0.0096 (11)	−0.0164 (12)

Geometric parameters (Å, º)

C1—O22	1.457 (2)	C18—H18B	0.98
C1—C14	1.514 (3)	C18—H18C	0.98
C1—C15	1.533 (3)	C19—H19B	0.98
C1—C2	1.548 (3)	C19—H19C	0.98
C2—O20	1.454 (2)	C19—H19A	0.98
C2—C3	1.537 (3)	O20—C21	1.334 (2)
C2—H2	1.0	C21—O23	1.196 (3)
C3—C4	1.530 (3)	C21—O22	1.347 (3)
C3—C8	1.561 (3)	O24—C25	1.346 (2)
C3—H3	1.0	C25—O26	1.213 (2)
C4—O41	1.438 (2)	C25—C27	1.490 (3)
C4—C5	1.530 (3)	C27—C32	1.389 (3)
C4—H4	1.0	C27—C28	1.391 (3)
C5—C6	1.524 (3)	C28—C29	1.383 (3)
C5—H5B	0.99	C28—H28	0.95
C5—H5A	0.99	C29—C30	1.379 (3)
C6—C7	1.512 (3)	C29—H29	0.95
C6—H6A	0.99	C30—C31	1.382 (3)
C6—H6B	0.99	C30—H30	0.95
C7—O24	1.456 (2)	C31—C32	1.379 (3)
C7—C8	1.537 (3)	C31—H31	0.95
C7—H7	1.0	C32—H32	0.95
C8—C19	1.537 (3)	O33—C34	1.428 (2)
C8—C9	1.553 (3)	C34—C35	1.491 (3)
C9—C10	1.543 (3)	C34—H34A	0.99
C9—H9B	0.99	C34—H34B	0.99
C9—H9A	0.99	C35—C36	1.390 (3)
C10—O33	1.436 (2)	C35—C40	1.396 (3)
C10—C11	1.508 (3)	C36—C37	1.379 (3)
C10—H10	1.0	C36—H36	0.95
C11—C12	1.348 (3)	C37—C38	1.380 (3)
C11—C15	1.554 (3)	C37—H37	0.95
C12—C13	1.473 (3)	C38—C39	1.374 (4)
C12—C18	1.502 (3)	C38—H38	0.95
C13—C14	1.330 (3)	C39—C40	1.375 (3)
C13—H13	0.95	C39—H39	0.95
C14—H14	0.95	C40—H40	0.95
C15—C16	1.537 (3)	O41—C42	1.400 (3)
C15—C17	1.541 (3)	C42—O43	1.405 (3)
C16—H16B	0.98	C42—H42B	0.99
C16—H16C	0.98	C42—H42A	0.99
C16—H16A	0.98	O43—C44	1.421 (3)
C17—H17A	0.98	C44—H44C	0.98
C17—H17B	0.98	C44—H44A	0.98
C17—H17C	0.98	C44—H44B	0.98
C18—H18A	0.98
O22—C1—C14	107.39 (16)	C15—C17—H17A	109.5
O22—C1—C15	112.26 (16)	C15—C17—H17B	109.5
C14—C1—C15	109.44 (17)	H17A—C17—H17B	109.5
O22—C1—C2	100.39 (15)	C15—C17—H17C	109.5
C14—C1—C2	115.12 (16)	H17A—C17—H17C	109.5
C15—C1—C2	111.91 (17)	H17B—C17—H17C	109.5
O20—C2—C3	114.77 (16)	C12—C18—H18A	109.5
O20—C2—C1	102.39 (15)	C12—C18—H18B	109.5
C3—C2—C1	116.91 (17)	H18A—C18—H18B	109.5
O20—C2—H2	107.4	C12—C18—H18C	109.5
C3—C2—H2	107.4	H18A—C18—H18C	109.5
C1—C2—H2	107.4	H18B—C18—H18C	109.5
C4—C3—C2	114.36 (16)	C8—C19—H19B	109.5
C4—C3—C8	112.76 (16)	C8—C19—H19C	109.5
C2—C3—C8	111.37 (16)	H19B—C19—H19C	109.5
C4—C3—H3	105.9	C8—C19—H19A	109.5
C2—C3—H3	105.9	H19B—C19—H19A	109.5
C8—C3—H3	105.9	H19C—C19—H19A	109.5
O41—C4—C3	104.79 (15)	C21—O20—C2	108.37 (16)
O41—C4—C5	109.40 (16)	O23—C21—O20	124.3 (2)
C3—C4—C5	109.75 (17)	O23—C21—O22	123.56 (19)
O41—C4—H4	110.9	O20—C21—O22	112.13 (18)
C3—C4—H4	110.9	C21—O22—C1	108.85 (15)
C5—C4—H4	110.9	C25—O24—C7	116.56 (15)
C6—C5—C4	114.71 (17)	O26—C25—O24	123.60 (19)
C6—C5—H5B	108.6	O26—C25—C27	123.88 (19)
C4—C5—H5B	108.6	O24—C25—C27	112.51 (17)
C6—C5—H5A	108.6	C32—C27—C28	119.65 (19)
C4—C5—H5A	108.6	C32—C27—C25	122.37 (18)
H5B—C5—H5A	107.6	C28—C27—C25	117.85 (19)
C7—C6—C5	110.62 (16)	C29—C28—C27	120.1 (2)
C7—C6—H6A	109.5	C29—C28—H28	120.0
C5—C6—H6A	109.5	C27—C28—H28	120.0
C7—C6—H6B	109.5	C30—C29—C28	120.0 (2)
C5—C6—H6B	109.5	C30—C29—H29	120.0
H6A—C6—H6B	108.1	C28—C29—H29	120.0
O24—C7—C6	110.82 (15)	C29—C30—C31	120.2 (2)
O24—C7—C8	108.01 (15)	C29—C30—H30	119.9
C6—C7—C8	112.06 (17)	C31—C30—H30	119.9
O24—C7—H7	108.6	C32—C31—C30	120.3 (2)
C6—C7—H7	108.6	C32—C31—H31	119.8
C8—C7—H7	108.6	C30—C31—H31	119.8
C19—C8—C7	110.94 (16)	C31—C32—C27	119.86 (19)
C19—C8—C9	104.78 (16)	C31—C32—H32	120.1
C7—C8—C9	111.49 (16)	C27—C32—H32	120.1
C19—C8—C3	110.89 (16)	C34—O33—C10	113.59 (15)
C7—C8—C3	104.62 (15)	O33—C34—C35	111.86 (17)
C9—C8—C3	114.26 (16)	O33—C34—H34A	109.2
C10—C9—C8	123.76 (17)	C35—C34—H34A	109.2
C10—C9—H9B	106.4	O33—C34—H34B	109.2
C8—C9—H9B	106.4	C35—C34—H34B	109.2
C10—C9—H9A	106.4	H34A—C34—H34B	107.9
C8—C9—H9A	106.4	C36—C35—C40	118.3 (2)
H9B—C9—H9A	106.5	C36—C35—C34	119.20 (19)
O33—C10—C11	113.16 (16)	C40—C35—C34	122.5 (2)
O33—C10—C9	103.42 (15)	C37—C36—C35	120.6 (2)
C11—C10—C9	114.58 (17)	C37—C36—H36	119.7
O33—C10—H10	108.5	C35—C36—H36	119.7
C11—C10—H10	108.5	C36—C37—C38	120.4 (2)
C9—C10—H10	108.5	C36—C37—H37	119.8
C12—C11—C10	119.94 (18)	C38—C37—H37	119.8
C12—C11—C15	117.22 (18)	C39—C38—C37	119.4 (2)
C10—C11—C15	121.82 (17)	C39—C38—H38	120.3
C11—C12—C13	118.68 (19)	C37—C38—H38	120.3
C11—C12—C18	126.2 (2)	C38—C39—C40	120.7 (2)
C13—C12—C18	114.38 (18)	C38—C39—H39	119.6
C14—C13—C12	118.85 (19)	C40—C39—H39	119.6
C14—C13—H13	120.6	C39—C40—C35	120.5 (2)
C12—C13—H13	120.6	C39—C40—H40	119.8
C13—C14—C1	119.8 (2)	C35—C40—H40	119.8
C13—C14—H14	120.1	C42—O41—C4	116.28 (16)
C1—C14—H14	120.1	O41—C42—O43	112.97 (18)
C1—C15—C16	112.74 (17)	O41—C42—H42B	109.0
C1—C15—C17	111.81 (17)	O43—C42—H42B	109.0
C16—C15—C17	104.00 (16)	O41—C42—H42A	109.0
C1—C15—C11	101.58 (15)	O43—C42—H42A	109.0
C16—C15—C11	117.71 (17)	H42B—C42—H42A	107.8
C17—C15—C11	109.19 (17)	C42—O43—C44	112.09 (17)
C15—C16—H16B	109.5	O43—C44—H44C	109.5
C15—C16—H16C	109.5	O43—C44—H44A	109.5
H16B—C16—H16C	109.5	H44C—C44—H44A	109.5
C15—C16—H16A	109.5	O43—C44—H44B	109.5
H16B—C16—H16A	109.5	H44C—C44—H44B	109.5
H16C—C16—H16A	109.5	H44A—C44—H44B	109.5
O22—C1—C2—O20	26.87 (18)	C3—C8—C9—C10	−51.5 (3)
C14—C1—C2—O20	−88.07 (19)	C8—C9—C10—O33	176.60 (17)
C15—C1—C2—O20	146.14 (16)	C8—C9—C10—C11	53.0 (3)
O22—C1—C2—C3	153.21 (16)	O33—C10—C11—C12	137.37 (19)
C14—C1—C2—C3	38.3 (3)	C9—C10—C11—C12	−104.4 (2)
C15—C1—C2—C3	−87.5 (2)	O33—C10—C11—C15	−54.5 (2)
O20—C2—C3—C4	4.3 (2)	C9—C10—C11—C15	63.8 (2)
C1—C2—C3—C4	−115.6 (2)	C10—C11—C12—C13	150.34 (18)
O20—C2—C3—C8	−124.98 (18)	C15—C11—C12—C13	−18.4 (3)
C1—C2—C3—C8	115.07 (19)	C10—C11—C12—C18	−19.5 (3)
C2—C3—C4—O41	58.5 (2)	C15—C11—C12—C18	171.80 (18)
C8—C3—C4—O41	−172.95 (15)	C11—C12—C13—C14	−17.7 (3)
C2—C3—C4—C5	175.84 (17)	C18—C12—C13—C14	153.33 (19)
C8—C3—C4—C5	−55.6 (2)	C12—C13—C14—C1	9.1 (3)
O41—C4—C5—C6	163.01 (17)	O22—C1—C14—C13	155.28 (18)
C3—C4—C5—C6	48.5 (2)	C15—C1—C14—C13	33.2 (2)
C4—C5—C6—C7	−50.2 (2)	C2—C1—C14—C13	−93.9 (2)
C5—C6—C7—O24	179.13 (16)	O22—C1—C15—C16	53.1 (2)
C5—C6—C7—C8	58.4 (2)	C14—C1—C15—C16	172.27 (16)
O24—C7—C8—C19	−65.5 (2)	C2—C1—C15—C16	−58.9 (2)
C6—C7—C8—C19	56.9 (2)	O22—C1—C15—C17	−63.6 (2)
O24—C7—C8—C9	50.9 (2)	C14—C1—C15—C17	55.5 (2)
C6—C7—C8—C9	173.24 (16)	C2—C1—C15—C17	−175.65 (16)
O24—C7—C8—C3	174.89 (15)	O22—C1—C15—C11	−179.97 (16)
C6—C7—C8—C3	−62.8 (2)	C14—C1—C15—C11	−60.82 (19)
C4—C3—C8—C19	−57.8 (2)	C2—C1—C15—C11	68.0 (2)
C2—C3—C8—C19	72.3 (2)	C12—C11—C15—C1	56.4 (2)
C4—C3—C8—C7	61.8 (2)	C10—C11—C15—C1	−112.1 (2)
C2—C3—C8—C7	−168.02 (16)	C12—C11—C15—C16	179.97 (18)
C4—C3—C8—C9	−175.95 (16)	C10—C11—C15—C16	11.5 (3)
C2—C3—C8—C9	−45.8 (2)	C12—C11—C15—C17	−61.8 (2)
C19—C8—C9—C10	−173.02 (18)	C10—C11—C15—C17	129.69 (19)
C7—C8—C9—C10	66.9 (2)	C3—C2—O20—C21	−149.52 (17)

Hydrogen-bond geometry (Å, º)

Cg is the centroid of the C35–C40 benzene ring.

D—H···A	D—H	H···A	D···A	D—H···A
C34—H34A···O43^i	0.99	2.42	3.377 (3)	163
C38—H38···O23^ii	0.95	2.44	3.295 (3)	149
C31—H31···O33^iii	0.95	2.49	3.426 (3)	168
C2—H2···O23^iv	1.00	2.51	3.433 (3)	153
C16—H16A···O23^iv	0.98	2.53	3.357 (3)	142
C19—H19C···O23^iv	0.98	2.54	3.477 (3)	160
C18—H18C···Cg^v	0.98	2.89	3.492 (3)	121

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