Crystal structure and Hirshfeld surface analysis of 2,2′-[(3,5-di-tert-butyl-4-hy­droxy­phen­yl)methanedi­yl]bis­(3-hy­droxy-5,5-di­methyl­cyclo­hex-2-en-1-one)

In the title compound, mol­ecules are linked together by O—H...O and C—H...O hydrogen bonds, forming zigzag chains that are parallel to the (001) plane and run along the b-axis direction. van der Waals inter­actions between these chains along the a and c axes maintain the mol­ecular packing.

Key indicators

Structure: I

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.039
• wR factor = 0.104
• Data-to-parameter ratio = 16.9

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT414_ALERT_2_B Short Intra D-H..H-X       H5O      ..H27A     .       1.86 Ang.
                                                      x,y,z  =      1_555 Check

Alert level C
PLAT414_ALERT_2_C Short Intra D-H..H-X       H5O      ..H26C     .       1.91 Ang.
                                                      x,y,z  =      1_555 Check
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.600          3 Report

Alert level G
PLAT142_ALERT_4_G s.u. on b - Axis Small or Missing ..............    0.00010 Ang.
PLAT143_ALERT_4_G s.u. on c - Axis Small or Missing ..............    0.00017 Ang.
PLAT802_ALERT_4_G CIF Input Record(s) with more than 80 Characters          1 Info
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         51 Note
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
   1 ALERT level B = A potentially serious problem, consider carefully
   2 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   5 ALERT level G = General information/check it is not something unexpected

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   3 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
   4 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

---

Computing details

Data collection: CrysAlis PRO 1.171.42.72a (Rigaku OD, 2022); cell refinement: CrysAlis PRO 1.171.42.72a (Rigaku OD, 2022); data reduction: CrysAlis PRO 1.171.42.72a (Rigaku OD, 2022); program(s) used to solve structure: SHELXT2014/5 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2018/3 (Sheldrick, 2015b); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: PLATON (Spek, 2020).

2,2'-[(3,5-Di-tert-butyl-4-hydroxyphenyl)methanediyl]bis(3-hydroxy-5,5-dimethylcyclohex-2-en-1-one)

Crystal data

C31H44O5	F(000) = 1080
Mr = 496.66	Dx = 1.189 Mg m^−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.54184 Å
a = 12.40591 (9) Å	Cell parameters from 41183 reflections
b = 10.98934 (10) Å	θ = 3.6–77.8°
c = 20.58063 (17) Å	µ = 0.63 mm^−1
β = 98.4293 (7)°	T = 100 K
V = 2775.50 (4) Å^3	Prism, colourless
Z = 4	0.33 × 0.21 × 0.18 mm

Data collection

XtaLAB Synergy, Dualflex, HyPix diffractometer	5540 reflections with I > 2σ(I)
Radiation source: micro-focus sealed X-ray tube	Rint = 0.047
φ and ω scans	θmax = 77.9°, θmin = 3.6°
Absorption correction: gaussian (CrysAlisPro; Rigaku OD, 2022)	h = −13→15
Tmin = 0.362, Tmax = 1.000	k = −13→13
61789 measured reflections	l = −26→26
5870 independent reflections

Refinement

Refinement on F^2	Primary atom site location: difference Fourier map
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.039	Hydrogen site location: mixed
wR(F^2) = 0.104	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ^2(Fo^2) + (0.0581P)^2 + 0.9674P] where P = (Fo^2 + 2Fc^2)/3
5870 reflections	(Δ/σ)max = 0.001
347 parameters	Δρmax = 0.27 e Å^−3
0 restraints	Δρmin = −0.26 e Å^−3

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.

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

	x	y	z	Uiso*/Ueq
O1	0.67352 (6)	0.68092 (7)	0.79581 (4)	0.02223 (17)
H1O	0.7151 (15)	0.6706 (16)	0.7621 (9)	0.046 (5)*
O2	0.39003 (6)	0.48506 (8)	0.65828 (4)	0.02641 (18)
O3	0.47791 (6)	0.57142 (7)	0.55974 (4)	0.02175 (17)
H3O	0.4532 (15)	0.5356 (17)	0.5969 (9)	0.049 (5)*
O4	0.79022 (6)	0.69306 (7)	0.69970 (3)	0.01951 (16)
O5	0.99582 (6)	0.26695 (8)	0.81386 (4)	0.02279 (17)
H5O	1.0464 (15)	0.2572 (16)	0.7907 (9)	0.041 (4)*
C1	0.61903 (8)	0.51072 (9)	0.68241 (5)	0.0160 (2)
H1	0.5758	0.4455	0.6566	0.019*
C2	0.54278 (8)	0.56043 (9)	0.72776 (5)	0.0171 (2)
C3	0.57463 (8)	0.63356 (9)	0.78073 (5)	0.0186 (2)
C4	0.50033 (9)	0.66692 (11)	0.82932 (6)	0.0245 (2)
H4A	0.4701	0.7491	0.8186	0.029*
H4B	0.5435	0.6707	0.8737	0.029*
C5	0.40583 (9)	0.57748 (10)	0.83053 (5)	0.0217 (2)
C6	0.35058 (9)	0.56319 (12)	0.75965 (6)	0.0265 (2)
H6A	0.2947	0.4985	0.7579	0.032*
H6B	0.3127	0.6401	0.7454	0.032*
C7	0.42799 (9)	0.53188 (10)	0.71194 (5)	0.0211 (2)
C8	0.32572 (10)	0.62886 (12)	0.87359 (6)	0.0307 (3)
H8A	0.3632	0.6401	0.9185	0.046*
H8B	0.2650	0.5719	0.8739	0.046*
H8C	0.2977	0.7073	0.8559	0.046*
C9	0.44652 (10)	0.45389 (12)	0.85835 (6)	0.0304 (3)
H9A	0.4965	0.4189	0.8307	0.046*
H9B	0.3844	0.3991	0.8590	0.046*
H9C	0.4848	0.4646	0.9031	0.046*
C10	0.64598 (8)	0.60075 (9)	0.63062 (5)	0.0162 (2)
C11	0.57732 (8)	0.61877 (9)	0.57293 (5)	0.0176 (2)
C12	0.60567 (8)	0.69745 (10)	0.51805 (5)	0.0197 (2)
H12A	0.5757	0.7800	0.5224	0.024*
H12B	0.5709	0.6634	0.4756	0.024*
C13	0.72887 (8)	0.70697 (10)	0.51767 (5)	0.0192 (2)
C14	0.78192 (8)	0.74319 (10)	0.58701 (5)	0.0193 (2)
H14A	0.8614	0.7292	0.5905	0.023*
H14B	0.7707	0.8315	0.5926	0.023*
C15	0.74074 (8)	0.67709 (9)	0.64281 (5)	0.0169 (2)
C16	0.75463 (10)	0.80530 (11)	0.46958 (6)	0.0266 (2)
H16A	0.7221	0.8826	0.4804	0.040*
H16B	0.7244	0.7814	0.4247	0.040*
H16C	0.8338	0.8148	0.4728	0.040*
C17	0.77368 (9)	0.58492 (10)	0.49695 (5)	0.0231 (2)
H17A	0.8532	0.5899	0.5002	0.035*
H17B	0.7422	0.5667	0.4515	0.035*
H17C	0.7543	0.5202	0.5259	0.035*
C18	0.72031 (8)	0.44419 (9)	0.71819 (5)	0.0169 (2)
C19	0.80443 (8)	0.41235 (9)	0.68346 (5)	0.0176 (2)
H19	0.7982	0.4341	0.6384	0.021*
C20	0.89755 (8)	0.34983 (9)	0.71204 (5)	0.0174 (2)
C21	0.90520 (8)	0.32072 (9)	0.77939 (5)	0.0177 (2)
C22	0.82019 (8)	0.34622 (9)	0.81580 (5)	0.0175 (2)
C23	0.72883 (8)	0.40755 (9)	0.78330 (5)	0.0177 (2)
H23	0.6702	0.4248	0.8068	0.021*
C24	0.98864 (9)	0.31798 (10)	0.67141 (5)	0.0206 (2)
C25	0.95624 (10)	0.35071 (13)	0.59845 (5)	0.0307 (3)
H25A	0.8885	0.3087	0.5811	0.046*
H25B	1.0142	0.3255	0.5738	0.046*
H25C	0.9454	0.4388	0.5941	0.046*
C26	1.09148 (9)	0.39337 (11)	0.69613 (6)	0.0249 (2)
H26A	1.0742	0.4803	0.6916	0.037*
H26B	1.1491	0.3734	0.6700	0.037*
H26C	1.1164	0.3743	0.7424	0.037*
C27	1.01253 (9)	0.17986 (11)	0.67306 (6)	0.0249 (2)
H27A	1.0304	0.1529	0.7188	0.037*
H27B	1.0742	0.1632	0.6496	0.037*
H27C	0.9481	0.1359	0.6519	0.037*
C28	0.82892 (9)	0.31386 (10)	0.88945 (5)	0.0190 (2)
C29	0.72191 (9)	0.33977 (11)	0.91629 (5)	0.0248 (2)
H29A	0.7048	0.4267	0.9118	0.037*
H29B	0.7299	0.3167	0.9628	0.037*
H29C	0.6628	0.2924	0.8914	0.037*
C30	0.85384 (9)	0.17769 (10)	0.90225 (5)	0.0221 (2)
H30A	0.7966	0.1284	0.8769	0.033*
H30B	0.8564	0.1604	0.9492	0.033*
H30C	0.9244	0.1578	0.8888	0.033*
C31	0.91838 (9)	0.39252 (10)	0.92908 (5)	0.0235 (2)
H31A	0.9879	0.3783	0.9130	0.035*
H31B	0.9254	0.3705	0.9757	0.035*
H31C	0.8987	0.4787	0.9237	0.035*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0206 (4)	0.0269 (4)	0.0198 (4)	−0.0059 (3)	0.0049 (3)	−0.0048 (3)
O2	0.0183 (4)	0.0367 (5)	0.0231 (4)	−0.0052 (3)	−0.0008 (3)	−0.0003 (3)
O3	0.0160 (4)	0.0296 (4)	0.0183 (4)	−0.0029 (3)	−0.0017 (3)	−0.0008 (3)
O4	0.0183 (4)	0.0242 (4)	0.0154 (3)	−0.0040 (3)	0.0005 (3)	−0.0014 (3)
O5	0.0179 (4)	0.0335 (4)	0.0168 (3)	0.0085 (3)	0.0021 (3)	0.0044 (3)
C1	0.0152 (5)	0.0165 (5)	0.0156 (4)	−0.0006 (4)	0.0002 (3)	−0.0001 (4)
C2	0.0156 (5)	0.0178 (5)	0.0178 (5)	0.0016 (4)	0.0017 (4)	0.0031 (4)
C3	0.0178 (5)	0.0184 (5)	0.0196 (5)	0.0007 (4)	0.0030 (4)	0.0029 (4)
C4	0.0252 (6)	0.0245 (5)	0.0254 (5)	−0.0009 (4)	0.0093 (4)	−0.0035 (4)
C5	0.0180 (5)	0.0250 (5)	0.0231 (5)	0.0034 (4)	0.0061 (4)	0.0048 (4)
C6	0.0157 (5)	0.0384 (7)	0.0255 (6)	0.0018 (4)	0.0034 (4)	0.0043 (5)
C7	0.0175 (5)	0.0236 (5)	0.0215 (5)	0.0004 (4)	0.0008 (4)	0.0044 (4)
C8	0.0269 (6)	0.0366 (7)	0.0312 (6)	0.0074 (5)	0.0129 (5)	0.0055 (5)
C9	0.0268 (6)	0.0315 (6)	0.0352 (6)	0.0062 (5)	0.0124 (5)	0.0131 (5)
C10	0.0162 (5)	0.0165 (5)	0.0157 (4)	0.0008 (4)	0.0015 (4)	−0.0007 (3)
C11	0.0169 (5)	0.0182 (5)	0.0173 (5)	0.0016 (4)	0.0009 (4)	−0.0022 (4)
C12	0.0198 (5)	0.0221 (5)	0.0161 (5)	0.0021 (4)	−0.0007 (4)	0.0009 (4)
C13	0.0203 (5)	0.0225 (5)	0.0145 (5)	0.0002 (4)	0.0015 (4)	0.0016 (4)
C14	0.0191 (5)	0.0210 (5)	0.0177 (5)	−0.0030 (4)	0.0022 (4)	0.0002 (4)
C15	0.0165 (5)	0.0180 (5)	0.0159 (4)	0.0018 (4)	0.0016 (4)	−0.0009 (4)
C16	0.0274 (6)	0.0315 (6)	0.0210 (5)	−0.0006 (5)	0.0033 (4)	0.0075 (4)
C17	0.0234 (5)	0.0273 (6)	0.0185 (5)	0.0028 (4)	0.0033 (4)	−0.0015 (4)
C18	0.0160 (5)	0.0163 (5)	0.0177 (5)	0.0002 (4)	0.0005 (4)	0.0001 (4)
C19	0.0189 (5)	0.0190 (5)	0.0147 (4)	0.0002 (4)	0.0015 (4)	0.0004 (4)
C20	0.0165 (5)	0.0188 (5)	0.0166 (5)	0.0005 (4)	0.0017 (4)	−0.0007 (4)
C21	0.0167 (5)	0.0184 (5)	0.0170 (5)	0.0018 (4)	−0.0003 (4)	0.0011 (4)
C22	0.0193 (5)	0.0175 (5)	0.0155 (5)	0.0004 (4)	0.0017 (4)	0.0007 (4)
C23	0.0168 (5)	0.0183 (5)	0.0182 (5)	0.0012 (4)	0.0036 (4)	0.0004 (4)
C24	0.0178 (5)	0.0278 (6)	0.0164 (5)	0.0046 (4)	0.0032 (4)	0.0019 (4)
C25	0.0249 (6)	0.0499 (8)	0.0182 (5)	0.0127 (5)	0.0067 (4)	0.0051 (5)
C26	0.0192 (5)	0.0281 (6)	0.0279 (5)	0.0018 (4)	0.0048 (4)	0.0071 (4)
C27	0.0223 (5)	0.0286 (6)	0.0235 (5)	0.0050 (4)	0.0024 (4)	−0.0053 (4)
C28	0.0211 (5)	0.0209 (5)	0.0151 (5)	0.0025 (4)	0.0029 (4)	0.0012 (4)
C29	0.0258 (6)	0.0315 (6)	0.0184 (5)	0.0060 (4)	0.0072 (4)	0.0039 (4)
C30	0.0265 (5)	0.0211 (5)	0.0186 (5)	0.0018 (4)	0.0028 (4)	0.0031 (4)
C31	0.0272 (6)	0.0237 (5)	0.0189 (5)	0.0006 (4)	0.0011 (4)	−0.0018 (4)

Geometric parameters (Å, º)

O1—C3	1.3268 (13)	C14—H14B	0.9900
O1—H1O	0.930 (19)	C16—H16A	0.9800
O2—C7	1.2466 (14)	C16—H16B	0.9800
O3—C11	1.3293 (13)	C16—H16C	0.9800
O3—H3O	0.950 (19)	C17—H17A	0.9800
O4—C15	1.2521 (12)	C17—H17B	0.9800
O5—C21	1.3720 (12)	C17—H17C	0.9800
O5—H5O	0.848 (19)	C18—C23	1.3882 (14)
C1—C2	1.5241 (14)	C18—C19	1.3931 (14)
C1—C10	1.5270 (14)	C19—C20	1.3977 (14)
C1—C18	1.5442 (13)	C19—H19	0.9500
C1—H1	1.0000	C20—C21	1.4121 (14)
C2—C3	1.3654 (15)	C20—C24	1.5414 (14)
C2—C7	1.4479 (14)	C21—C22	1.4085 (14)
C3—C4	1.5015 (14)	C22—C23	1.4014 (14)
C4—C5	1.5329 (15)	C22—C28	1.5453 (13)
C4—H4A	0.9900	C23—H23	0.9500
C4—H4B	0.9900	C24—C25	1.5390 (14)
C5—C6	1.5262 (16)	C24—C26	1.5436 (16)
C5—C9	1.5305 (15)	C24—C27	1.5459 (16)
C5—C8	1.5329 (15)	C25—H25A	0.9800
C6—C7	1.5104 (15)	C25—H25B	0.9800
C6—H6A	0.9900	C25—H25C	0.9800
C6—H6B	0.9900	C26—H26A	0.9800
C8—H8A	0.9800	C26—H26B	0.9800
C8—H8B	0.9800	C26—H26C	0.9800
C8—H8C	0.9800	C27—H27A	0.9800
C9—H9A	0.9800	C27—H27B	0.9800
C9—H9B	0.9800	C27—H27C	0.9800
C9—H9C	0.9800	C28—C29	1.5373 (14)
C10—C11	1.3703 (14)	C28—C31	1.5423 (15)
C10—C15	1.4361 (14)	C28—C30	1.5429 (14)
C11—C12	1.5044 (14)	C29—H29A	0.9800
C12—C13	1.5332 (14)	C29—H29B	0.9800
C12—H12A	0.9900	C29—H29C	0.9800
C12—H12B	0.9900	C30—H30A	0.9800
C13—C16	1.5305 (15)	C30—H30B	0.9800
C13—C14	1.5338 (14)	C30—H30C	0.9800
C13—C17	1.5360 (15)	C31—H31A	0.9800
C14—C15	1.5098 (14)	C31—H31B	0.9800
C14—H14A	0.9900	C31—H31C	0.9800
C3—O1—H1O	111.9 (11)	H16A—C16—H16B	109.5
C11—O3—H3O	113.4 (11)	C13—C16—H16C	109.5
C21—O5—H5O	112.4 (12)	H16A—C16—H16C	109.5
C2—C1—C10	114.48 (8)	H16B—C16—H16C	109.5
C2—C1—C18	114.35 (8)	C13—C17—H17A	109.5
C10—C1—C18	113.17 (8)	C13—C17—H17B	109.5
C2—C1—H1	104.4	H17A—C17—H17B	109.5
C10—C1—H1	104.4	C13—C17—H17C	109.5
C18—C1—H1	104.4	H17A—C17—H17C	109.5
C3—C2—C7	117.84 (9)	H17B—C17—H17C	109.5
C3—C2—C1	124.54 (9)	C23—C18—C19	117.75 (9)
C7—C2—C1	117.58 (9)	C23—C18—C1	122.62 (9)
O1—C3—C2	124.54 (9)	C19—C18—C1	119.51 (9)
O1—C3—C4	112.67 (9)	C18—C19—C20	122.87 (9)
C2—C3—C4	122.78 (10)	C18—C19—H19	118.6
C3—C4—C5	113.58 (9)	C20—C19—H19	118.6
C3—C4—H4A	108.9	C19—C20—C21	117.18 (9)
C5—C4—H4A	108.9	C19—C20—C24	120.65 (9)
C3—C4—H4B	108.9	C21—C20—C24	122.14 (9)
C5—C4—H4B	108.9	O5—C21—C22	115.54 (9)
H4A—C4—H4B	107.7	O5—C21—C20	122.49 (9)
C6—C5—C9	110.09 (10)	C22—C21—C20	121.96 (9)
C6—C5—C4	106.73 (9)	C23—C22—C21	117.25 (9)
C9—C5—C4	111.35 (9)	C23—C22—C28	120.95 (9)
C6—C5—C8	110.61 (9)	C21—C22—C28	121.73 (9)
C9—C5—C8	108.47 (9)	C18—C23—C22	122.82 (9)
C4—C5—C8	109.60 (10)	C18—C23—H23	118.6
C7—C6—C5	113.92 (9)	C22—C23—H23	118.6
C7—C6—H6A	108.8	C25—C24—C20	111.64 (9)
C5—C6—H6A	108.8	C25—C24—C26	106.33 (9)
C7—C6—H6B	108.8	C20—C24—C26	109.60 (9)
C5—C6—H6B	108.8	C25—C24—C27	105.83 (9)
H6A—C6—H6B	107.7	C20—C24—C27	111.38 (9)
O2—C7—C2	121.33 (10)	C26—C24—C27	111.91 (9)
O2—C7—C6	118.45 (10)	C24—C25—H25A	109.5
C2—C7—C6	120.18 (10)	C24—C25—H25B	109.5
C5—C8—H8A	109.5	H25A—C25—H25B	109.5
C5—C8—H8B	109.5	C24—C25—H25C	109.5
H8A—C8—H8B	109.5	H25A—C25—H25C	109.5
C5—C8—H8C	109.5	H25B—C25—H25C	109.5
H8A—C8—H8C	109.5	C24—C26—H26A	109.5
H8B—C8—H8C	109.5	C24—C26—H26B	109.5
C5—C9—H9A	109.5	H26A—C26—H26B	109.5
C5—C9—H9B	109.5	C24—C26—H26C	109.5
H9A—C9—H9B	109.5	H26A—C26—H26C	109.5
C5—C9—H9C	109.5	H26B—C26—H26C	109.5
H9A—C9—H9C	109.5	C24—C27—H27A	109.5
H9B—C9—H9C	109.5	C24—C27—H27B	109.5
C11—C10—C15	117.13 (9)	H27A—C27—H27B	109.5
C11—C10—C1	121.77 (9)	C24—C27—H27C	109.5
C15—C10—C1	120.93 (8)	H27A—C27—H27C	109.5
O3—C11—C10	124.11 (9)	H27B—C27—H27C	109.5
O3—C11—C12	112.55 (8)	C29—C28—C31	107.37 (9)
C10—C11—C12	123.32 (9)	C29—C28—C30	106.28 (9)
C11—C12—C13	112.71 (8)	C31—C28—C30	110.04 (9)
C11—C12—H12A	109.1	C29—C28—C22	111.71 (8)
C13—C12—H12A	109.0	C31—C28—C22	109.34 (8)
C11—C12—H12B	109.0	C30—C28—C22	111.97 (8)
C13—C12—H12B	109.1	C28—C29—H29A	109.5
H12A—C12—H12B	107.8	C28—C29—H29B	109.5
C16—C13—C12	110.75 (9)	H29A—C29—H29B	109.5
C16—C13—C14	108.46 (9)	C28—C29—H29C	109.5
C12—C13—C14	107.76 (8)	H29A—C29—H29C	109.5
C16—C13—C17	108.58 (9)	H29B—C29—H29C	109.5
C12—C13—C17	110.09 (9)	C28—C30—H30A	109.5
C14—C13—C17	111.20 (8)	C28—C30—H30B	109.5
C15—C14—C13	115.84 (9)	H30A—C30—H30B	109.5
C15—C14—H14A	108.3	C28—C30—H30C	109.5
C13—C14—H14A	108.3	H30A—C30—H30C	109.5
C15—C14—H14B	108.3	H30B—C30—H30C	109.5
C13—C14—H14B	108.3	C28—C31—H31A	109.5
H14A—C14—H14B	107.4	C28—C31—H31B	109.5
O4—C15—C10	121.45 (9)	H31A—C31—H31B	109.5
O4—C15—C14	118.02 (9)	C28—C31—H31C	109.5
C10—C15—C14	120.51 (9)	H31A—C31—H31C	109.5
C13—C16—H16A	109.5	H31B—C31—H31C	109.5
C13—C16—H16B	109.5
C10—C1—C2—C3	−80.31 (12)	C11—C10—C15—O4	159.09 (10)
C18—C1—C2—C3	52.59 (13)	C1—C10—C15—O4	−16.20 (15)
C10—C1—C2—C7	97.16 (11)	C11—C10—C15—C14	−19.37 (14)
C18—C1—C2—C7	−129.95 (9)	C1—C10—C15—C14	165.34 (9)
C7—C2—C3—O1	−170.29 (10)	C13—C14—C15—O4	171.74 (9)
C1—C2—C3—O1	7.17 (16)	C13—C14—C15—C10	−9.75 (14)
C7—C2—C3—C4	10.96 (15)	C2—C1—C18—C23	14.42 (14)
C1—C2—C3—C4	−171.58 (9)	C10—C1—C18—C23	147.93 (10)
O1—C3—C4—C5	−156.69 (9)	C2—C1—C18—C19	−169.61 (9)
C2—C3—C4—C5	22.20 (15)	C10—C1—C18—C19	−36.10 (13)
C3—C4—C5—C6	−51.77 (12)	C23—C18—C19—C20	−2.46 (15)
C3—C4—C5—C9	68.40 (12)	C1—C18—C19—C20	−178.62 (9)
C3—C4—C5—C8	−171.58 (9)	C18—C19—C20—C21	−1.08 (15)
C9—C5—C6—C7	−69.22 (12)	C18—C19—C20—C24	−179.42 (10)
C4—C5—C6—C7	51.76 (13)	C19—C20—C21—O5	−175.48 (9)
C8—C5—C6—C7	170.91 (10)	C24—C20—C21—O5	2.84 (16)
C3—C2—C7—O2	166.72 (10)	C19—C20—C21—C22	3.91 (15)
C1—C2—C7—O2	−10.92 (15)	C24—C20—C21—C22	−177.77 (10)
C3—C2—C7—C6	−10.86 (15)	O5—C21—C22—C23	176.38 (9)
C1—C2—C7—C6	171.50 (9)	C20—C21—C22—C23	−3.06 (15)
C5—C6—C7—O2	159.86 (10)	O5—C21—C22—C28	−0.72 (14)
C5—C6—C7—C2	−22.50 (15)	C20—C21—C22—C28	179.85 (9)
C2—C1—C10—C11	−82.41 (12)	C19—C18—C23—C22	3.40 (15)
C18—C1—C10—C11	144.14 (9)	C1—C18—C23—C22	179.43 (9)
C2—C1—C10—C15	92.66 (11)	C21—C22—C23—C18	−0.72 (15)
C18—C1—C10—C15	−40.79 (12)	C28—C22—C23—C18	176.40 (10)
C15—C10—C11—O3	−167.64 (9)	C19—C20—C24—C25	−6.12 (15)
C1—C10—C11—O3	7.61 (15)	C21—C20—C24—C25	175.62 (10)
C15—C10—C11—C12	10.77 (15)	C19—C20—C24—C26	111.43 (11)
C1—C10—C11—C12	−173.97 (9)	C21—C20—C24—C26	−66.83 (13)
O3—C11—C12—C13	−155.18 (9)	C19—C20—C24—C27	−124.18 (10)
C10—C11—C12—C13	26.24 (14)	C21—C20—C24—C27	57.56 (13)
C11—C12—C13—C16	−169.61 (9)	C23—C22—C28—C29	8.36 (14)
C11—C12—C13—C14	−51.12 (11)	C21—C22—C28—C29	−174.66 (10)
C11—C12—C13—C17	70.30 (11)	C23—C22—C28—C31	−110.35 (11)
C16—C13—C14—C15	163.76 (9)	C21—C22—C28—C31	66.63 (12)
C12—C13—C14—C15	43.82 (12)	C23—C22—C28—C30	127.43 (10)
C17—C13—C14—C15	−76.92 (11)	C21—C22—C28—C30	−55.59 (13)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O···O4	0.930 (19)	1.711 (19)	2.6201 (11)	164.7 (17)
O3—H3O···O2	0.950 (19)	1.68 (2)	2.6174 (11)	170.3 (17)
O5—H5O···O4^i	0.848 (19)	2.128 (18)	2.8285 (11)	139.7 (16)
C14—H14A···O5^ii	0.99	2.48	3.1912 (12)	128

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