5-tert-Butyl-3-{[6-(2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyl­tetra­hydro­furo[3,4-d][1,3]dioxol-4-yl­oxy]meth­yl}-2-hydroxy­benzaldehyde

Theare are two independent mol­ecules in the asymmetric unit of the title compound, C₂₄H₃₄O_8. The crystal packing is mainly determined by weak inter­molecular C—H...O hydrogen bonds and van der Waals inter­actions.

Key indicators

• Single-crystal X-ray study
• T = 113 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.041
• wR factor = 0.104
• Data-to-parameter ratio = 9.9

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT127_ALERT_1_C Implicit Hall Symbol  Inconsistent with Explicit    -P 2ybc
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       3.26 Ratio
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.82 Ratio

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           27.87
           From the CIF: _reflns_number_total               5939
           Count of symmetry unique reflns         6000
           Completeness (_total/calc)             98.98%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured         0
           Fraction of Friedel pairs measured     0.000
           Are heavy atom types Z>Si present         no

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

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 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
   1 ALERT type 4 Improvement, methodology, query or suggestion

---

Computing details

Data collection: CrystalClear (Rigaku/MSC, 2005); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: CrystalStructure (Rigaku/MSC, 2005); software used to prepare material for publication: CrystalStructure.

5-tert-Butyl-3-{[6-(2,2-dimethyl-1,3-dioxolan-4-yl)-2,2- dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yloxy]methyl}-2- hydroxybenzaldehyde

Crystal data

C24H34O8	F(000) = 968
Mr = 450.51	Dx = 1.287 Mg m^−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71070 Å
Hall symbol: -P 2ybc	Cell parameters from 6830 reflections
a = 12.7880 (19) Å	θ = 1.6–27.9°
b = 6.7749 (10) Å	µ = 0.10 mm^−1
c = 26.859 (4) Å	T = 113 K
β = 92.118 (2)°	Block, colourless
V = 2325.4 (6) Å^3	0.32 × 0.20 × 0.16 mm
Z = 4

Data collection

Rigaku Saturn CCD area-detector diffractometer	5939 independent reflections
Radiation source: rotating anode	4809 reflections with I > 2σ(I)
Confocal monochromator	Rint = 0.038
Detector resolution: 7.31 pixels mm^-1	θmax = 27.9°, θmin = 1.6°
ω scans	h = −16→16
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −8→7
Tmin = 0.970, Tmax = 0.985	l = −34→34
20584 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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.104	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	w = 1/[σ^2(Fo^2) + (0.0633P)^2] where P = (Fo^2 + 2Fc^2)/3
5939 reflections	(Δ/σ)max = 0.001
598 parameters	Δρmax = 0.36 e Å^−3
1 restraint	Δρmin = −0.23 e Å^−3

Special details

Experimental. Analysis calculated for C₂₄H₃₄O₈: C 63.98, H7.61%; found: C 63.78, H 7.45%. ¹H NMR (CDCl₃, δ, p.p.m.): 1.33(s,9H), 1.44(s,12H), 3.61(q, J=3.6, 4.2, 3.6 Hz, 1H), 4.06(d, J=5.4 Hz, 2H), 4.46–4.90(m,6H), 7.46(d, J=2.7 Hz,1H), 7.79(d, J=2.4 Hz,1H), 9.90(s,1H), 11.09(s,1H). ¹³C NMR (CDCl₃, δ, p.p.m.): 197.0, 157.4, 142.69, 134.6, 129.4, 126.0, 120.0, 114.1, 109.5, 103.0, 80.1, 79.4, 77.3, 73.6, 67.1, 66.4, 31.5,27.3, 26.0, 25.5, 25.4. IR (KBr): ν (cm^-1) 3423, 2972, 2938, 2870, 1666, 1620, 1461, 1437, 1379, 1290, 1275, 1258, 1246, 1215, 1146, 1119, 1089, 1070, 1057, 1005, 901, 847.

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
O1	0.91593 (10)	0.3987 (2)	0.53454 (5)	0.0196 (3)
O2	1.02030 (11)	0.6998 (3)	0.65133 (5)	0.0271 (4)
O3	1.08587 (11)	0.6557 (3)	0.57443 (6)	0.0296 (5)
O4	0.76486 (11)	0.7683 (2)	0.54200 (6)	0.0199 (4)
O5	0.65579 (11)	0.5508 (2)	0.50069 (6)	0.0215 (4)
O6	0.75627 (10)	0.3427 (2)	0.57202 (5)	0.0177 (3)
O7	0.89507 (11)	0.2272 (3)	0.69972 (6)	0.0258 (4)
H7	0.913 (2)	0.240 (5)	0.7300 (10)	0.039*
O8	0.88326 (11)	0.2509 (3)	0.79662 (6)	0.0263 (4)
O9	0.58285 (11)	0.0076 (3)	0.96376 (5)	0.0192 (3)
O10	0.48277 (11)	0.2354 (3)	0.85229 (6)	0.0289 (4)
O11	0.41827 (11)	0.2964 (3)	0.92771 (5)	0.0250 (4)
O12	0.73800 (11)	0.3717 (2)	0.95802 (5)	0.0199 (3)
O13	0.84706 (11)	0.1416 (3)	0.99473 (6)	0.0219 (4)
O14	0.73971 (10)	−0.0635 (2)	0.92468 (5)	0.0176 (3)
O15	0.59794 (11)	−0.2747 (3)	0.79814 (6)	0.0221 (4)
H15	0.579 (2)	−0.282 (5)	0.7684 (10)	0.033*
O16	0.61340 (11)	−0.3151 (3)	0.70180 (6)	0.0252 (4)
C1	0.92996 (16)	0.6050 (4)	0.52297 (8)	0.0186 (5)
H1	0.9790	0.6131	0.4949	0.022*
C2	0.82470 (16)	0.6815 (4)	0.50394 (8)	0.0194 (5)
H2	0.8308	0.7704	0.4745	0.023*
C3	0.76042 (15)	0.4975 (4)	0.49166 (8)	0.0194 (5)
H3	0.7679	0.4579	0.4561	0.023*
C4	0.80899 (15)	0.3417 (4)	0.52716 (8)	0.0193 (5)
H4	0.8044	0.2080	0.5115	0.023*
C5	0.97909 (15)	0.7186 (4)	0.56669 (8)	0.0214 (5)
H5	0.9783	0.8626	0.5585	0.026*
C6	0.93160 (16)	0.6890 (4)	0.61768 (7)	0.0204 (5)
H6A	0.8804	0.7942	0.6246	0.024*
H6B	0.8967	0.5591	0.6197	0.024*
C7	1.10545 (17)	0.6165 (5)	0.62707 (9)	0.0283 (6)
C8	1.11021 (19)	0.3940 (5)	0.63521 (10)	0.0352 (7)
H8A	1.1232	0.3664	0.6707	0.053*
H8B	1.1669	0.3382	0.6161	0.053*
H8C	1.0435	0.3345	0.6241	0.053*
C9	1.20460 (18)	0.7193 (6)	0.64393 (9)	0.0407 (7)
H9A	1.1980	0.8610	0.6372	0.061*
H9B	1.2634	0.6658	0.6258	0.061*
H9C	1.2171	0.6981	0.6797	0.061*
C10	0.65674 (16)	0.7317 (4)	0.52891 (8)	0.0218 (5)
C11	0.59823 (16)	0.7074 (4)	0.57620 (8)	0.0249 (5)
H11A	0.6257	0.5926	0.5946	0.037*
H11B	0.5237	0.6877	0.5679	0.037*
H11C	0.6073	0.8260	0.5968	0.037*
C12	0.61268 (18)	0.8966 (4)	0.49570 (9)	0.0312 (6)
H12A	0.6117	1.0201	0.5147	0.047*
H12B	0.5413	0.8628	0.4842	0.047*
H12C	0.6567	0.9128	0.4669	0.047*
C13	0.79383 (16)	0.1888 (4)	0.60520 (8)	0.0194 (5)
H13A	0.8698	0.2057	0.6125	0.023*
H13B	0.7826	0.0582	0.5894	0.023*
C14	0.73549 (16)	0.2002 (4)	0.65257 (8)	0.0173 (4)
C15	0.78955 (15)	0.2165 (4)	0.69860 (8)	0.0184 (4)
C16	0.73270 (15)	0.2205 (4)	0.74268 (8)	0.0176 (4)
C17	0.62358 (15)	0.2100 (4)	0.74022 (8)	0.0186 (4)
H17	0.5865	0.2128	0.7702	0.022*
C18	0.56744 (15)	0.1954 (4)	0.69456 (8)	0.0180 (5)
C19	0.62634 (16)	0.1927 (4)	0.65201 (8)	0.0185 (5)
H19	0.5900	0.1851	0.6206	0.022*
C20	0.78781 (16)	0.2378 (4)	0.79084 (8)	0.0224 (5)
H20	0.7472	0.2390	0.8198	0.027*
C21	0.44747 (16)	0.1876 (4)	0.69335 (8)	0.0214 (5)
C22	0.41108 (18)	0.0097 (4)	0.72357 (10)	0.0314 (6)
H22A	0.3344	0.0065	0.7231	0.047*
H22B	0.4383	0.0212	0.7580	0.047*
H22C	0.4373	−0.1122	0.7089	0.047*
C23	0.40579 (18)	0.3771 (4)	0.71705 (10)	0.0315 (6)
H23A	0.4252	0.4914	0.6970	0.047*
H23B	0.4362	0.3911	0.7509	0.047*
H23C	0.3294	0.3697	0.7183	0.047*
C24	0.40202 (17)	0.1704 (5)	0.64015 (9)	0.0343 (7)
H24A	0.4279	0.0495	0.6248	0.051*
H24B	0.4235	0.2850	0.6207	0.051*
H24C	0.3255	0.1658	0.6407	0.051*
C25	0.57271 (15)	0.2129 (4)	0.97700 (8)	0.0181 (4)
H25	0.5236	0.2220	1.0050	0.022*
C26	0.67982 (16)	0.2804 (4)	0.99632 (8)	0.0198 (5)
H26	0.6761	0.3646	1.0268	0.024*
C27	0.74244 (15)	0.0923 (4)	1.00574 (8)	0.0186 (5)
H27	0.7379	0.0491	1.0412	0.022*
C28	0.68843 (15)	−0.0578 (4)	0.97029 (8)	0.0180 (5)
H28	0.6900	−0.1917	0.9860	0.022*
C29	0.52813 (15)	0.3369 (4)	0.93401 (7)	0.0188 (5)
H29	0.5382	0.4799	0.9421	0.023*
C30	0.57120 (16)	0.2942 (4)	0.88228 (7)	0.0193 (5)
H30A	0.6038	0.4139	0.8685	0.023*
H30B	0.6241	0.1875	0.8843	0.023*
C31	0.39389 (17)	0.3107 (5)	0.87526 (9)	0.0312 (6)
C32	0.3010 (2)	0.1842 (7)	0.86324 (11)	0.0557 (11)
H32A	0.2868	0.1836	0.8271	0.084*
H32B	0.2400	0.2367	0.8799	0.084*
H32C	0.3150	0.0492	0.8748	0.084*
C33	0.3774 (2)	0.5282 (5)	0.86059 (9)	0.0389 (7)
H33A	0.4405	0.6039	0.8697	0.058*
H33B	0.3179	0.5818	0.8782	0.058*
H33C	0.3632	0.5376	0.8246	0.058*
C34	0.84638 (16)	0.3301 (4)	0.96909 (8)	0.0203 (5)
C35	0.89372 (17)	0.4858 (4)	1.00377 (9)	0.0299 (6)
H35A	0.8940	0.6135	0.9866	0.045*
H35B	0.9656	0.4485	1.0135	0.045*
H35C	0.8521	0.4960	1.0336	0.045*
C36	0.90176 (17)	0.3086 (4)	0.92078 (8)	0.0253 (5)
H36A	0.8719	0.1970	0.9019	0.038*
H36B	0.9764	0.2851	0.9279	0.038*
H36C	0.8929	0.4298	0.9012	0.038*
C37	0.69266 (16)	−0.2076 (4)	0.89179 (8)	0.0210 (5)
H37A	0.6201	−0.1676	0.8825	0.025*
H37B	0.6901	−0.3369	0.9089	0.025*
C38	0.75537 (16)	−0.2256 (3)	0.84562 (8)	0.0171 (5)
C39	0.70394 (15)	−0.2600 (4)	0.79991 (8)	0.0173 (5)
C40	0.76215 (15)	−0.2783 (4)	0.75646 (8)	0.0178 (4)
C41	0.87189 (16)	−0.2680 (4)	0.76004 (8)	0.0191 (5)
H41	0.9107	−0.2817	0.7307	0.023*
C42	0.92517 (16)	−0.2382 (3)	0.80565 (8)	0.0192 (5)
C43	0.86457 (16)	−0.2152 (3)	0.84735 (8)	0.0184 (5)
H43	0.8994	−0.1913	0.8786	0.022*
C44	0.70873 (16)	−0.3062 (4)	0.70828 (8)	0.0217 (5)
H44	0.7504	−0.3184	0.6799	0.026*
C45	1.04541 (16)	−0.2330 (4)	0.80789 (9)	0.0220 (5)
C46	1.08826 (17)	−0.1983 (5)	0.86128 (9)	0.0317 (6)
H46A	1.0654	−0.3056	0.8828	0.047*
H46B	1.0618	−0.0723	0.8736	0.047*
H46C	1.1649	−0.1948	0.8616	0.047*
C47	1.08636 (18)	−0.4316 (4)	0.78949 (10)	0.0322 (6)
H47A	1.1630	−0.4306	0.7911	0.048*
H47B	1.0613	−0.4533	0.7550	0.048*
H47C	1.0609	−0.5379	0.8106	0.048*
C48	1.08484 (17)	−0.0666 (5)	0.77467 (9)	0.0296 (6)
H48A	1.1615	−0.0678	0.7753	0.044*
H48B	1.0603	0.0607	0.7870	0.044*
H48C	1.0579	−0.0865	0.7404	0.044*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0167 (7)	0.0188 (9)	0.0236 (8)	−0.0002 (6)	0.0040 (6)	−0.0004 (7)
O2	0.0225 (8)	0.0409 (11)	0.0179 (8)	0.0003 (9)	−0.0002 (6)	−0.0010 (8)
O3	0.0160 (7)	0.0532 (14)	0.0198 (8)	−0.0020 (8)	0.0033 (6)	−0.0026 (8)
O4	0.0197 (7)	0.0206 (9)	0.0193 (8)	0.0015 (6)	−0.0005 (6)	−0.0024 (6)
O5	0.0175 (7)	0.0251 (9)	0.0217 (8)	0.0006 (7)	−0.0027 (6)	−0.0058 (7)
O6	0.0187 (7)	0.0192 (8)	0.0154 (7)	0.0017 (6)	0.0051 (6)	0.0012 (7)
O7	0.0152 (7)	0.0402 (11)	0.0222 (8)	−0.0023 (8)	0.0021 (6)	0.0003 (9)
O8	0.0203 (7)	0.0352 (11)	0.0233 (9)	0.0001 (8)	−0.0017 (7)	0.0017 (8)
O9	0.0152 (7)	0.0200 (8)	0.0224 (8)	−0.0001 (6)	0.0028 (6)	−0.0011 (7)
O10	0.0243 (8)	0.0415 (11)	0.0209 (8)	−0.0042 (9)	0.0008 (6)	−0.0109 (8)
O11	0.0149 (7)	0.0405 (11)	0.0197 (8)	0.0006 (7)	0.0024 (6)	0.0006 (8)
O12	0.0163 (7)	0.0214 (9)	0.0220 (8)	−0.0024 (7)	−0.0001 (6)	0.0029 (7)
O13	0.0163 (7)	0.0271 (9)	0.0220 (8)	0.0002 (7)	−0.0008 (6)	0.0037 (7)
O14	0.0180 (6)	0.0195 (8)	0.0156 (7)	−0.0025 (6)	0.0043 (6)	−0.0021 (6)
O15	0.0149 (7)	0.0319 (9)	0.0196 (8)	−0.0002 (8)	0.0010 (6)	−0.0001 (8)
O16	0.0216 (8)	0.0315 (11)	0.0222 (8)	−0.0010 (8)	−0.0022 (7)	0.0009 (8)
C1	0.0184 (9)	0.0205 (12)	0.0170 (11)	−0.0040 (9)	0.0022 (8)	0.0001 (9)
C2	0.0224 (10)	0.0224 (13)	0.0135 (11)	−0.0013 (10)	0.0026 (8)	0.0016 (9)
C3	0.0198 (10)	0.0234 (12)	0.0150 (10)	−0.0002 (9)	0.0014 (8)	−0.0026 (9)
C4	0.0187 (10)	0.0225 (12)	0.0168 (11)	−0.0023 (9)	0.0038 (8)	−0.0030 (9)
C5	0.0189 (10)	0.0261 (12)	0.0194 (11)	−0.0032 (10)	0.0022 (8)	0.0000 (11)
C6	0.0204 (10)	0.0247 (13)	0.0161 (11)	−0.0004 (10)	0.0015 (8)	−0.0021 (10)
C7	0.0203 (11)	0.0455 (17)	0.0189 (12)	0.0003 (12)	0.0002 (9)	−0.0030 (12)
C8	0.0297 (12)	0.0391 (17)	0.0369 (15)	0.0044 (13)	0.0038 (11)	−0.0008 (13)
C9	0.0254 (12)	0.063 (2)	0.0335 (15)	−0.0135 (15)	−0.0027 (11)	0.0017 (16)
C10	0.0193 (10)	0.0221 (12)	0.0237 (12)	0.0010 (10)	−0.0022 (9)	−0.0023 (10)
C11	0.0215 (10)	0.0287 (13)	0.0245 (12)	0.0028 (11)	0.0003 (9)	−0.0042 (11)
C12	0.0301 (12)	0.0321 (15)	0.0309 (14)	0.0083 (12)	−0.0067 (11)	0.0035 (12)
C13	0.0225 (10)	0.0164 (12)	0.0194 (11)	0.0020 (9)	0.0029 (9)	0.0007 (9)
C14	0.0203 (9)	0.0129 (11)	0.0189 (11)	−0.0003 (9)	0.0045 (8)	0.0001 (9)
C15	0.0172 (9)	0.0150 (11)	0.0232 (11)	−0.0003 (10)	0.0038 (8)	0.0028 (10)
C16	0.0181 (9)	0.0167 (11)	0.0182 (11)	−0.0006 (10)	0.0017 (8)	0.0021 (10)
C17	0.0183 (9)	0.0183 (11)	0.0194 (11)	−0.0001 (10)	0.0039 (8)	0.0021 (10)
C18	0.0182 (10)	0.0149 (11)	0.0209 (11)	0.0005 (10)	0.0008 (8)	0.0023 (10)
C19	0.0204 (10)	0.0180 (12)	0.0172 (10)	0.0021 (9)	0.0004 (8)	−0.0008 (9)
C20	0.0233 (10)	0.0235 (13)	0.0206 (11)	0.0007 (11)	0.0032 (9)	0.0040 (10)
C21	0.0166 (9)	0.0237 (13)	0.0239 (12)	0.0001 (10)	−0.0002 (9)	−0.0012 (10)
C22	0.0187 (11)	0.0289 (15)	0.0465 (16)	−0.0040 (11)	0.0005 (11)	0.0068 (13)
C23	0.0198 (10)	0.0324 (16)	0.0426 (15)	0.0048 (11)	0.0027 (11)	−0.0068 (13)
C24	0.0192 (10)	0.052 (2)	0.0310 (14)	0.0010 (12)	−0.0016 (10)	−0.0038 (13)
C25	0.0172 (9)	0.0195 (11)	0.0179 (11)	0.0012 (10)	0.0051 (8)	−0.0003 (9)
C26	0.0220 (10)	0.0223 (13)	0.0153 (11)	−0.0004 (10)	0.0018 (9)	−0.0007 (9)
C27	0.0164 (9)	0.0240 (12)	0.0155 (11)	0.0007 (9)	0.0008 (8)	0.0014 (9)
C28	0.0170 (9)	0.0215 (12)	0.0158 (10)	0.0017 (9)	0.0051 (8)	0.0046 (9)
C29	0.0149 (9)	0.0243 (12)	0.0175 (10)	0.0007 (9)	0.0023 (8)	0.0000 (10)
C30	0.0190 (9)	0.0216 (12)	0.0174 (11)	0.0013 (9)	0.0022 (8)	0.0013 (9)
C31	0.0199 (11)	0.0546 (19)	0.0191 (12)	−0.0010 (13)	0.0006 (9)	−0.0011 (13)
C32	0.0324 (14)	0.092 (3)	0.0426 (18)	−0.0242 (18)	−0.0015 (13)	−0.0113 (19)
C33	0.0313 (13)	0.058 (2)	0.0276 (14)	0.0159 (14)	0.0030 (11)	0.0058 (14)
C34	0.0174 (9)	0.0200 (12)	0.0234 (12)	−0.0010 (9)	−0.0018 (9)	0.0014 (10)
C35	0.0249 (11)	0.0329 (15)	0.0318 (13)	−0.0063 (11)	−0.0022 (10)	−0.0022 (12)
C36	0.0226 (10)	0.0312 (14)	0.0222 (12)	−0.0022 (11)	0.0031 (9)	0.0042 (11)
C37	0.0227 (10)	0.0184 (12)	0.0222 (12)	−0.0061 (10)	0.0042 (9)	−0.0029 (9)
C38	0.0193 (9)	0.0155 (12)	0.0167 (11)	−0.0020 (9)	0.0032 (8)	0.0000 (8)
C39	0.0150 (9)	0.0147 (11)	0.0224 (11)	0.0011 (9)	0.0031 (8)	0.0025 (9)
C40	0.0180 (9)	0.0166 (11)	0.0189 (11)	0.0004 (10)	0.0006 (8)	−0.0001 (10)
C41	0.0177 (9)	0.0192 (12)	0.0207 (11)	0.0015 (10)	0.0035 (8)	−0.0016 (10)
C42	0.0156 (9)	0.0189 (13)	0.0232 (12)	0.0009 (9)	0.0019 (9)	−0.0011 (9)
C43	0.0193 (9)	0.0168 (12)	0.0191 (11)	−0.0018 (9)	−0.0007 (9)	−0.0015 (9)
C44	0.0203 (10)	0.0215 (13)	0.0233 (12)	−0.0005 (10)	0.0014 (9)	0.0009 (10)
C45	0.0159 (9)	0.0258 (14)	0.0245 (12)	−0.0015 (9)	0.0003 (9)	−0.0048 (10)
C46	0.0185 (10)	0.0418 (17)	0.0342 (14)	−0.0029 (12)	−0.0040 (10)	−0.0051 (13)
C47	0.0208 (11)	0.0310 (16)	0.0446 (16)	0.0044 (11)	−0.0009 (11)	−0.0090 (13)
C48	0.0182 (10)	0.0383 (16)	0.0327 (14)	−0.0063 (11)	0.0044 (10)	−0.0010 (13)

Geometric parameters (Å, º)

O1—C4	1.428 (2)	C18—C21	1.534 (3)
O1—C1	1.444 (3)	C19—H19	0.9500
O2—C7	1.407 (3)	C20—H20	0.9500
O2—C6	1.426 (2)	C21—C24	1.527 (3)
O3—C5	1.438 (2)	C21—C22	1.535 (4)
O3—C7	1.451 (3)	C21—C23	1.537 (4)
O4—C2	1.426 (3)	C22—H22A	0.9800
O4—C10	1.436 (2)	C22—H22B	0.9800
O5—C3	1.415 (2)	C22—H22C	0.9800
O5—C10	1.441 (3)	C23—H23A	0.9800
O6—C4	1.402 (2)	C23—H23B	0.9800
O6—C13	1.442 (3)	C23—H23C	0.9800
O7—C15	1.351 (2)	C24—H24A	0.9800
O7—H7	0.84 (3)	C24—H24B	0.9800
O8—C20	1.228 (2)	C24—H24C	0.9800
O9—C28	1.426 (2)	C25—C26	1.517 (3)
O9—C25	1.443 (3)	C25—C29	1.521 (3)
O10—C31	1.409 (3)	C25—H25	1.0000
O10—C30	1.421 (2)	C26—C27	1.521 (3)
O11—C31	1.435 (3)	C26—H26	1.0000
O11—C29	1.435 (2)	C27—C28	1.539 (3)
O12—C26	1.432 (3)	C27—H27	1.0000
O12—C34	1.435 (2)	C28—H28	1.0000
O13—C27	1.421 (2)	C29—C30	1.541 (3)
O13—C34	1.451 (3)	C29—H29	1.0000
O14—C28	1.411 (2)	C30—H30A	0.9900
O14—C37	1.433 (3)	C30—H30B	0.9900
O15—C39	1.358 (2)	C31—C32	1.491 (4)
O15—H15	0.83 (3)	C31—C33	1.538 (5)
O16—C44	1.227 (2)	C32—H32A	0.9800
C1—C2	1.513 (3)	C32—H32B	0.9800
C1—C5	1.520 (3)	C32—H32C	0.9800
C1—H1	1.0000	C33—H33A	0.9800
C2—C3	1.522 (3)	C33—H33B	0.9800
C2—H2	1.0000	C33—H33C	0.9800
C3—C4	1.538 (3)	C34—C36	1.508 (3)
C3—H3	1.0000	C34—C35	1.519 (3)
C4—H4	1.0000	C35—H35A	0.9800
C5—C6	1.532 (3)	C35—H35B	0.9800
C5—H5	1.0000	C35—H35C	0.9800
C6—H6A	0.9900	C36—H36A	0.9800
C6—H6B	0.9900	C36—H36B	0.9800
C7—C9	1.502 (3)	C36—H36C	0.9800
C7—C8	1.524 (4)	C37—C38	1.506 (3)
C8—H8A	0.9800	C37—H37A	0.9900
C8—H8B	0.9800	C37—H37B	0.9900
C8—H8C	0.9800	C38—C39	1.391 (3)
C9—H9A	0.9800	C38—C43	1.397 (3)
C9—H9B	0.9800	C39—C40	1.413 (3)
C9—H9C	0.9800	C40—C41	1.405 (3)
C10—C11	1.507 (3)	C40—C44	1.453 (3)
C10—C12	1.524 (4)	C41—C42	1.394 (3)
C11—H11A	0.9800	C41—H41	0.9500
C11—H11B	0.9800	C42—C43	1.394 (3)
C11—H11C	0.9800	C42—C45	1.537 (3)
C12—H12A	0.9800	C43—H43	0.9500
C12—H12B	0.9800	C44—H44	0.9500
C12—H12C	0.9800	C45—C47	1.532 (4)
C13—C14	1.501 (3)	C45—C46	1.534 (3)
C13—H13A	0.9900	C45—C48	1.534 (4)
C13—H13B	0.9900	C46—H46A	0.9800
C14—C19	1.396 (3)	C46—H46B	0.9800
C14—C15	1.398 (3)	C46—H46C	0.9800
C15—C16	1.412 (3)	C47—H47A	0.9800
C16—C17	1.396 (3)	C47—H47B	0.9800
C16—C20	1.455 (3)	C47—H47C	0.9800
C17—C18	1.402 (3)	C48—H48A	0.9800
C17—H17	0.9500	C48—H48B	0.9800
C18—C19	1.392 (3)	C48—H48C	0.9800
C4—O1—C1	110.96 (16)	H23B—C23—H23C	109.5
C7—O2—C6	107.28 (17)	C21—C24—H24A	109.5
C5—O3—C7	108.89 (16)	C21—C24—H24B	109.5
C2—O4—C10	106.89 (16)	H24A—C24—H24B	109.5
C3—O5—C10	108.51 (16)	C21—C24—H24C	109.5
C4—O6—C13	111.59 (16)	H24A—C24—H24C	109.5
C15—O7—H7	105.5 (19)	H24B—C24—H24C	109.5
C28—O9—C25	111.28 (16)	O9—C25—C26	106.65 (17)
C31—O10—C30	106.76 (18)	O9—C25—C29	112.30 (18)
C31—O11—C29	106.21 (16)	C26—C25—C29	113.68 (19)
C26—O12—C34	106.83 (16)	O9—C25—H25	108.0
C27—O13—C34	108.45 (16)	C26—C25—H25	108.0
C28—O14—C37	110.84 (16)	C29—C25—H25	108.0
C39—O15—H15	106.7 (18)	O12—C26—C25	111.77 (17)
O1—C1—C2	106.72 (17)	O12—C26—C27	101.37 (17)
O1—C1—C5	112.01 (19)	C25—C26—C27	105.53 (19)
C2—C1—C5	115.1 (2)	O12—C26—H26	112.5
O1—C1—H1	107.6	C25—C26—H26	112.5
C2—C1—H1	107.6	C27—C26—H26	112.5
C5—C1—H1	107.6	O13—C27—C26	105.22 (18)
O4—C2—C1	113.15 (16)	O13—C27—C28	115.52 (18)
O4—C2—C3	101.15 (17)	C26—C27—C28	103.24 (16)
C1—C2—C3	105.04 (19)	O13—C27—H27	110.8
O4—C2—H2	112.3	C26—C27—H27	110.8
C1—C2—H2	112.3	C28—C27—H27	110.8
C3—C2—H2	112.3	O14—C28—O9	111.72 (15)
O5—C3—C2	105.09 (19)	O14—C28—C27	110.05 (17)
O5—C3—C4	115.56 (18)	O9—C28—C27	105.77 (18)
C2—C3—C4	103.00 (16)	O14—C28—H28	109.7
O5—C3—H3	110.9	O9—C28—H28	109.7
C2—C3—H3	110.9	C27—C28—H28	109.7
C4—C3—H3	110.9	O11—C29—C25	108.77 (18)
O6—C4—O1	111.58 (16)	O11—C29—C30	103.81 (16)
O6—C4—C3	109.49 (17)	C25—C29—C30	116.39 (19)
O1—C4—C3	105.27 (18)	O11—C29—H29	109.2
O6—C4—H4	110.1	C25—C29—H29	109.2
O1—C4—H4	110.1	C30—C29—H29	109.2
C3—C4—H4	110.1	O10—C30—C29	105.09 (16)
O3—C5—C1	108.94 (19)	O10—C30—H30A	110.7
O3—C5—C6	103.74 (16)	C29—C30—H30A	110.7
C1—C5—C6	117.27 (19)	O10—C30—H30B	110.7
O3—C5—H5	108.9	C29—C30—H30B	110.7
C1—C5—H5	108.9	H30A—C30—H30B	108.8
C6—C5—H5	108.9	O10—C31—O11	104.82 (18)
O2—C6—C5	103.16 (16)	O10—C31—C32	110.3 (3)
O2—C6—H6A	111.1	O11—C31—C32	108.4 (2)
C5—C6—H6A	111.1	O10—C31—C33	109.9 (2)
O2—C6—H6B	111.1	O11—C31—C33	109.8 (2)
C5—C6—H6B	111.1	C32—C31—C33	113.2 (2)
H6A—C6—H6B	109.1	C31—C32—H32A	109.5
O2—C7—O3	105.62 (18)	C31—C32—H32B	109.5
O2—C7—C9	109.5 (2)	H32A—C32—H32B	109.5
O3—C7—C9	108.8 (2)	C31—C32—H32C	109.5
O2—C7—C8	110.9 (2)	H32A—C32—H32C	109.5
O3—C7—C8	109.0 (2)	H32B—C32—H32C	109.5
C9—C7—C8	112.7 (2)	C31—C33—H33A	109.5
C7—C8—H8A	109.5	C31—C33—H33B	109.5
C7—C8—H8B	109.5	H33A—C33—H33B	109.5
H8A—C8—H8B	109.5	C31—C33—H33C	109.5
C7—C8—H8C	109.5	H33A—C33—H33C	109.5
H8A—C8—H8C	109.5	H33B—C33—H33C	109.5
H8B—C8—H8C	109.5	O12—C34—O13	105.10 (17)
C7—C9—H9A	109.5	O12—C34—C36	108.75 (17)
C7—C9—H9B	109.5	O13—C34—C36	109.2 (2)
H9A—C9—H9B	109.5	O12—C34—C35	110.53 (19)
C7—C9—H9C	109.5	O13—C34—C35	108.97 (17)
H9A—C9—H9C	109.5	C36—C34—C35	113.9 (2)
H9B—C9—H9C	109.5	C34—C35—H35A	109.5
O4—C10—O5	105.38 (17)	C34—C35—H35B	109.5
O4—C10—C11	108.44 (17)	H35A—C35—H35B	109.5
O5—C10—C11	110.8 (2)	C34—C35—H35C	109.5
O4—C10—C12	110.4 (2)	H35A—C35—H35C	109.5
O5—C10—C12	108.63 (17)	H35B—C35—H35C	109.5
C11—C10—C12	112.9 (2)	C34—C36—H36A	109.5
C10—C11—H11A	109.5	C34—C36—H36B	109.5
C10—C11—H11B	109.5	H36A—C36—H36B	109.5
H11A—C11—H11B	109.5	C34—C36—H36C	109.5
C10—C11—H11C	109.5	H36A—C36—H36C	109.5
H11A—C11—H11C	109.5	H36B—C36—H36C	109.5
H11B—C11—H11C	109.5	O14—C37—C38	109.77 (17)
C10—C12—H12A	109.5	O14—C37—H37A	109.7
C10—C12—H12B	109.5	C38—C37—H37A	109.7
H12A—C12—H12B	109.5	O14—C37—H37B	109.7
C10—C12—H12C	109.5	C38—C37—H37B	109.7
H12A—C12—H12C	109.5	H37A—C37—H37B	108.2
H12B—C12—H12C	109.5	C39—C38—C43	118.5 (2)
O6—C13—C14	108.80 (18)	C39—C38—C37	119.44 (18)
O6—C13—H13A	109.9	C43—C38—C37	122.03 (18)
C14—C13—H13A	109.9	O15—C39—C38	118.80 (19)
O6—C13—H13B	109.9	O15—C39—C40	121.36 (18)
C14—C13—H13B	109.9	C38—C39—C40	119.84 (18)
H13A—C13—H13B	108.3	C41—C40—C39	119.64 (18)
C19—C14—C15	118.28 (19)	C41—C40—C44	120.20 (19)
C19—C14—C13	121.14 (18)	C39—C40—C44	120.15 (18)
C15—C14—C13	120.58 (18)	C42—C41—C40	121.5 (2)
O7—C15—C14	119.00 (19)	C42—C41—H41	119.3
O7—C15—C16	121.68 (18)	C40—C41—H41	119.3
C14—C15—C16	119.32 (18)	C43—C42—C41	117.00 (19)
C17—C16—C15	120.26 (18)	C43—C42—C45	123.45 (18)
C17—C16—C20	119.78 (19)	C41—C42—C45	119.56 (19)
C15—C16—C20	119.96 (19)	C42—C43—C38	123.53 (19)
C16—C17—C18	121.58 (19)	C42—C43—H43	118.2
C16—C17—H17	119.2	C38—C43—H43	118.2
C18—C17—H17	119.2	O16—C44—C40	124.4 (2)
C19—C18—C17	116.38 (18)	O16—C44—H44	117.8
C19—C18—C21	123.58 (18)	C40—C44—H44	117.8
C17—C18—C21	120.03 (19)	C47—C45—C46	108.8 (2)
C18—C19—C14	124.17 (18)	C47—C45—C48	109.5 (2)
C18—C19—H19	117.9	C46—C45—C48	108.5 (2)
C14—C19—H19	117.9	C47—C45—C42	108.71 (19)
O8—C20—C16	124.4 (2)	C46—C45—C42	111.24 (19)
O8—C20—H20	117.8	C48—C45—C42	110.11 (18)
C16—C20—H20	117.8	C45—C46—H46A	109.5
C24—C21—C18	111.61 (18)	C45—C46—H46B	109.5
C24—C21—C22	108.8 (2)	H46A—C46—H46B	109.5
C18—C21—C22	109.78 (19)	C45—C46—H46C	109.5
C24—C21—C23	109.0 (2)	H46A—C46—H46C	109.5
C18—C21—C23	108.90 (19)	H46B—C46—H46C	109.5
C22—C21—C23	108.7 (2)	C45—C47—H47A	109.5
C21—C22—H22A	109.5	C45—C47—H47B	109.5
C21—C22—H22B	109.5	H47A—C47—H47B	109.5
H22A—C22—H22B	109.5	C45—C47—H47C	109.5
C21—C22—H22C	109.5	H47A—C47—H47C	109.5
H22A—C22—H22C	109.5	H47B—C47—H47C	109.5
H22B—C22—H22C	109.5	C45—C48—H48A	109.5
C21—C23—H23A	109.5	C45—C48—H48B	109.5
C21—C23—H23B	109.5	H48A—C48—H48B	109.5
H23A—C23—H23B	109.5	C45—C48—H48C	109.5
C21—C23—H23C	109.5	H48A—C48—H48C	109.5
H23A—C23—H23C	109.5	H48B—C48—H48C	109.5
C4—O1—C1—C2	−3.5 (2)	C28—O9—C25—C26	−3.4 (2)
C4—O1—C1—C5	123.40 (18)	C28—O9—C25—C29	121.77 (17)
C10—O4—C2—C1	−148.0 (2)	C34—O12—C26—C25	−148.42 (19)
C10—O4—C2—C3	−36.1 (2)	C34—O12—C26—C27	−36.4 (2)
O1—C1—C2—O4	93.8 (2)	O9—C25—C26—O12	95.1 (2)
C5—C1—C2—O4	−31.2 (3)	C29—C25—C26—O12	−29.2 (3)
O1—C1—C2—C3	−15.7 (2)	O9—C25—C26—C27	−14.2 (2)
C5—C1—C2—C3	−140.6 (2)	C29—C25—C26—C27	−138.54 (19)
C10—O5—C3—C2	−14.4 (2)	C34—O13—C27—C26	−12.6 (2)
C10—O5—C3—C4	98.4 (2)	C34—O13—C27—C28	100.6 (2)
O4—C2—C3—O5	30.8 (2)	O12—C26—C27—O13	29.8 (2)
C1—C2—C3—O5	148.66 (17)	C25—C26—C27—O13	146.42 (17)
O4—C2—C3—C4	−90.62 (17)	O12—C26—C27—C28	−91.75 (17)
C1—C2—C3—C4	27.3 (2)	C25—C26—C27—C28	24.9 (2)
C13—O6—C4—O1	−68.2 (2)	C37—O14—C28—O9	−64.8 (2)
C13—O6—C4—C3	175.67 (17)	C37—O14—C28—C27	178.02 (17)
C1—O1—C4—O6	−97.7 (2)	C25—O9—C28—O14	−100.3 (2)
C1—O1—C4—C3	21.0 (2)	C25—O9—C28—C27	19.4 (2)
O5—C3—C4—O6	−23.5 (3)	O13—C27—C28—O14	−20.6 (3)
C2—C3—C4—O6	90.49 (19)	C26—C27—C28—O14	93.68 (19)
O5—C3—C4—O1	−143.57 (18)	O13—C27—C28—O9	−141.43 (18)
C2—C3—C4—O1	−29.6 (2)	C26—C27—C28—O9	−27.1 (2)
C7—O3—C5—C1	−132.7 (2)	C31—O11—C29—C25	−146.1 (2)
C7—O3—C5—C6	−7.0 (3)	C31—O11—C29—C30	−21.6 (3)
O1—C1—C5—O3	69.0 (2)	O9—C25—C29—O11	74.2 (2)
C2—C1—C5—O3	−168.88 (19)	C26—C25—C29—O11	−164.64 (18)
O1—C1—C5—C6	−48.4 (3)	O9—C25—C29—C30	−42.6 (3)
C2—C1—C5—C6	73.8 (3)	C26—C25—C29—C30	78.6 (3)
C7—O2—C6—C5	−34.3 (3)	C31—O10—C30—C29	21.7 (3)
O3—C5—C6—O2	24.7 (3)	O11—C29—C30—O10	0.2 (3)
C1—C5—C6—O2	144.8 (2)	C25—C29—C30—O10	119.7 (2)
C6—O2—C7—O3	30.4 (3)	C30—O10—C31—O11	−35.8 (3)
C6—O2—C7—C9	147.5 (2)	C30—O10—C31—C32	−152.3 (2)
C6—O2—C7—C8	−87.5 (2)	C30—O10—C31—C33	82.2 (2)
C5—O3—C7—O2	−13.6 (3)	C29—O11—C31—O10	35.8 (3)
C5—O3—C7—C9	−131.1 (2)	C29—O11—C31—C32	153.6 (3)
C5—O3—C7—C8	105.7 (2)	C29—O11—C31—C33	−82.2 (2)
C2—O4—C10—O5	28.5 (2)	C26—O12—C34—O13	29.7 (2)
C2—O4—C10—C11	147.2 (2)	C26—O12—C34—C36	146.5 (2)
C2—O4—C10—C12	−88.6 (2)	C26—O12—C34—C35	−87.7 (2)
C3—O5—C10—O4	−7.7 (2)	C27—O13—C34—O12	−9.6 (2)
C3—O5—C10—C11	−124.79 (19)	C27—O13—C34—C36	−126.14 (18)
C3—O5—C10—C12	110.62 (19)	C27—O13—C34—C35	108.85 (19)
C4—O6—C13—C14	179.15 (17)	C28—O14—C37—C38	−174.24 (17)
O6—C13—C14—C19	55.7 (3)	O14—C37—C38—C39	−144.3 (2)
O6—C13—C14—C15	−125.0 (2)	O14—C37—C38—C43	37.8 (3)
C19—C14—C15—O7	−178.9 (2)	C43—C38—C39—O15	178.5 (2)
C13—C14—C15—O7	1.7 (4)	C37—C38—C39—O15	0.6 (3)
C19—C14—C15—C16	1.4 (4)	C43—C38—C39—C40	−1.7 (3)
C13—C14—C15—C16	−178.0 (2)	C37—C38—C39—C40	−179.6 (2)
O7—C15—C16—C17	179.7 (2)	O15—C39—C40—C41	−178.1 (2)
C14—C15—C16—C17	−0.6 (4)	C38—C39—C40—C41	2.1 (4)
O7—C15—C16—C20	0.4 (4)	O15—C39—C40—C44	2.3 (4)
C14—C15—C16—C20	−179.9 (2)	C38—C39—C40—C44	−177.5 (2)
C15—C16—C17—C18	0.0 (4)	C39—C40—C41—C42	−0.6 (4)
C20—C16—C17—C18	179.3 (2)	C44—C40—C41—C42	179.0 (2)
C16—C17—C18—C19	−0.2 (4)	C40—C41—C42—C43	−1.2 (4)
C16—C17—C18—C21	−179.0 (2)	C40—C41—C42—C45	178.5 (2)
C17—C18—C19—C14	1.1 (4)	C41—C42—C43—C38	1.6 (4)
C21—C18—C19—C14	179.8 (2)	C45—C42—C43—C38	−178.1 (2)
C15—C14—C19—C18	−1.7 (4)	C39—C38—C43—C42	−0.2 (4)
C13—C14—C19—C18	177.7 (2)	C37—C38—C43—C42	177.7 (2)
C17—C16—C20—O8	−178.8 (2)	C41—C40—C44—O16	−179.3 (2)
C15—C16—C20—O8	0.5 (4)	C39—C40—C44—O16	0.2 (4)
C19—C18—C21—C24	1.7 (3)	C43—C42—C45—C47	119.3 (3)
C17—C18—C21—C24	−179.6 (2)	C41—C42—C45—C47	−60.4 (3)
C19—C18—C21—C22	122.4 (3)	C43—C42—C45—C46	−0.4 (3)
C17—C18—C21—C22	−58.8 (3)	C41—C42—C45—C46	179.9 (2)
C19—C18—C21—C23	−118.7 (3)	C43—C42—C45—C48	−120.7 (2)
C17—C18—C21—C23	60.0 (3)	C41—C42—C45—C48	59.6 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O15—H15···O16	0.83 (3)	1.87 (3)	2.617 (2)	150 (3)
O7—H7···O8	0.84 (3)	1.84 (3)	2.618 (2)	152 (3)
C13—H13B···O4^i	0.99	2.35	3.330 (3)	172
C37—H37B···O12^i	0.99	2.44	3.398 (3)	163

Symmetry code: (i) x, y−1, z.