(+)-Cedrol hemihydrate: a natural product derived from drying eastern red cedar (Juniperus virginiana) wood

Cedrol-like com­pounds are of pharmacological inter­est due to their diverse range of medicinal effects and are used globally in traditional medicines and cosmetics. Many cedrol tautomers are known from mol­ecular studies but few have been studied in crystalline form by X-ray diffraction. Acicular white crystals collected from the wood of eastern red cedar (Juniperus virginiana) are determined to be (+)-cedrol hemihydrate, namely, (1S,2R,5S,7R,8R)-2,6,6,8-tetra­methyl­tri­cyclo­[5.3.1.0^1,5]undecan-8-ol hemihydrate, C₁₅H₂₆O·0.5H₂O, a novel packing of two unique cedrol mol­ecules (Z′ = 2) with a single water mol­ecule [space group P2₁2₁2₁; a = 6.1956 (1), b = 14.5363 (1), and c = 30.9294 (4) Å]. The hydrogen bonding forms a one-dimensional spiral chain running along the a axis, following the chirality of the cedrol mol­ecule, through hydrogen-bonding inter­actions with a right-handed helical configuration in graph-set notation Δ-C₃³(6) > a > c > b. The crystal packing and symmetry are different from crystalline isocedrol due to the different hydrogen-bonding geometry.

Computing details

(1S,2R,5S,7R,8R)-2,6,6,8-Tetramethyltricyclo[5.3.1.01,5]undecan-8-ol hemihydrate

Crystal data

C15H26O·0.5H2O	Dx = 1.103 Mg m^−3
Mr = 231.36	Cu Kα radiation, λ = 1.54184 Å
Orthorhombic, P212121	Cell parameters from 19499 reflections
a = 6.1956 (1) Å	θ = 3.4–67.3°
b = 14.5363 (1) Å	µ = 0.52 mm^−1
c = 30.9294 (4) Å	T = 250 K
V = 2785.54 (6) Å^3	Acicular prism, white
Z = 8	0.33 × 0.04 × 0.03 mm
F(000) = 1032

Data collection

Rigaku HighFlux HomeLab instrument equipped with a MicroMax-007 HF X-ray generator, Osmic VariMax optics and Dectris EIGER R 4M hybrid photon-counting detector diffractometer	5019 independent reflections
Radiation source: Rotating-anode X-ray tube, Rigaku (Cu) X-ray Source	4632 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.033
ω scans	θmax = 67.8°, θmin = 3.4°
Absorption correction: multi-scan (CrysAlis PRO; Rigaku OD, 2019)	h = −6→7
Tmin = 0.876, Tmax = 1.000	k = −16→17
39835 measured reflections	l = −37→37

Refinement

Refinement on F^2	Hydrogen site location: mixed
Least-squares matrix: full	Only H-atom displacement parameters refined
R[F^2 > 2σ(F^2)] = 0.036	w = 1/[σ^2(Fo^2) + (0.0597P)^2 + 0.2164P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.099	(Δ/σ)max < 0.001
S = 1.06	Δρmax = 0.16 e Å^−3
5019 reflections	Δρmin = −0.14 e Å^−3
373 parameters	Absolute structure: Flack x determined using 1836 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
3 restraints	Absolute structure parameter: −0.02 (6)
Primary atom site location: structure-invariant direct methods

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	0.0778 (3)	0.37262 (9)	0.07694 (5)	0.0533 (4)
H1	0.182 (6)	0.353 (2)	0.0599 (11)	0.088 (10)*
C1	0.0831 (4)	0.65872 (13)	0.08169 (7)	0.0474 (5)
C2	0.0810 (5)	0.76594 (14)	0.08433 (9)	0.0649 (6)
H2A	−0.067022	0.784586	0.092597	0.092 (10)*
C3	0.2275 (6)	0.78799 (17)	0.12246 (9)	0.0787 (8)
H3A	0.379064	0.789311	0.113438	0.134 (16)*
H3B	0.190034	0.847706	0.135111	0.082 (9)*
C4	0.1884 (6)	0.71133 (16)	0.15440 (9)	0.0759 (8)
H4A	0.051703	0.720048	0.169818	0.110 (13)*
H4B	0.306124	0.707107	0.175457	0.116 (13)*
C5	0.1804 (4)	0.62575 (13)	0.12536 (7)	0.0491 (5)
H5	0.330804	0.605862	0.119881	0.050 (6)*
C6	0.0485 (4)	0.53953 (13)	0.13939 (6)	0.0487 (5)
C7	−0.0862 (3)	0.51652 (12)	0.09785 (6)	0.0438 (4)
H7	−0.220609	0.484153	0.106078	0.050 (6)*
C8	0.0270 (3)	0.46414 (13)	0.06118 (6)	0.0450 (4)
C9	0.2351 (4)	0.51310 (14)	0.04771 (7)	0.0515 (5)
H9A	0.282715	0.488452	0.019803	0.062 (7)*
H9B	0.347744	0.499521	0.069016	0.050 (6)*
C10	0.2105 (4)	0.61814 (14)	0.04380 (7)	0.0536 (5)
H10A	0.353917	0.646474	0.042809	0.073 (8)*
H10B	0.136229	0.632797	0.016678	0.063 (7)*
C11	−0.1400 (3)	0.61380 (13)	0.08172 (8)	0.0511 (5)
H11A	−0.202779	0.612504	0.052644	0.057 (6)*
H11B	−0.239145	0.645456	0.101423	0.056 (7)*
C12	0.1383 (9)	0.81825 (19)	0.04430 (11)	0.1017 (14)
H12A	0.123814	0.883686	0.049730	0.093 (9)*
H12B	0.042073	0.800457	0.021013	0.159 (19)*
H12C	0.286056	0.804546	0.036196	0.108 (14)*
C13	−0.1111 (5)	0.55957 (19)	0.17635 (8)	0.0747 (8)
H13A	−0.207037	0.609122	0.167865	0.080 (9)*
H13B	−0.031748	0.577432	0.202042	0.086 (9)*
H13C	−0.195160	0.504769	0.182419	0.085 (9)*
C14	0.1981 (5)	0.46415 (16)	0.15599 (8)	0.0631 (6)
H14A	0.267068	0.484465	0.182472	0.085 (9)*
H14B	0.307434	0.451109	0.134393	0.057 (6)*
H14C	0.114988	0.408897	0.161654	0.079 (8)*
C15	−0.1232 (5)	0.45165 (16)	0.02239 (8)	0.0644 (6)
H15A	−0.261720	0.428660	0.032227	0.080 (9)*
H15B	−0.059842	0.408040	0.002334	0.098 (10)*
H15C	−0.143247	0.510335	0.008016	0.077 (8)*
O2	0.7904 (3)	0.22351 (10)	0.07159 (5)	0.0565 (4)
H2	0.896 (6)	0.269 (2)	0.0768 (10)	0.092 (10)*
C16	0.7290 (3)	0.03607 (12)	0.17296 (6)	0.0426 (4)
C17	0.7014 (4)	−0.03382 (14)	0.21057 (7)	0.0527 (5)
H17	0.818646	−0.021103	0.231489	0.065 (7)*
C18	0.4923 (4)	−0.00440 (17)	0.23210 (8)	0.0597 (6)
H18A	0.483791	−0.027480	0.261823	0.076 (8)*
H18B	0.366689	−0.026315	0.215840	0.072 (8)*
C19	0.5064 (4)	0.09999 (16)	0.23125 (8)	0.0610 (6)
H19A	0.611071	0.122752	0.252454	0.075 (8)*
H19B	0.365479	0.128176	0.236915	0.103 (11)*
C20	0.5818 (3)	0.11896 (13)	0.18485 (7)	0.0472 (4)
H20	0.453291	0.116434	0.165871	0.052 (6)*
C21	0.7102 (4)	0.20785 (14)	0.17309 (7)	0.0528 (5)
C22	0.9003 (3)	0.16950 (13)	0.14461 (7)	0.0454 (4)
H22	1.025059	0.211966	0.145996	0.059 (6)*
C23	0.8527 (3)	0.14417 (13)	0.09714 (6)	0.0464 (5)
C24	0.6650 (4)	0.07661 (15)	0.09405 (7)	0.0526 (5)
H24A	0.665044	0.048909	0.065163	0.065 (7)*
H24B	0.529497	0.110652	0.097373	0.050 (6)*
C25	0.6721 (4)	−0.00077 (14)	0.12801 (6)	0.0508 (5)
H25A	0.531090	−0.031242	0.129173	0.077 (8)*
H25B	0.779546	−0.046671	0.119335	0.063 (7)*
C26	0.9524 (3)	0.08041 (14)	0.16943 (7)	0.0465 (5)
H26A	1.052784	0.041314	0.153241	0.058 (6)*
H26B	1.013250	0.093598	0.198019	0.061 (7)*
C27	0.7155 (6)	−0.13548 (16)	0.19953 (10)	0.0784 (8)
H27A	0.598905	−0.151680	0.180028	0.077 (9)*
H27B	0.703671	−0.171561	0.225801	0.091 (9)*
H27C	0.852859	−0.148095	0.185699	0.121 (14)*
C28	0.8098 (6)	0.25455 (19)	0.21342 (9)	0.0764 (8)
H28A	0.695210	0.275691	0.232346	0.102 (11)*
H28B	0.897010	0.306576	0.204453	0.110 (12)*
H28C	0.899540	0.210646	0.228739	0.119 (13)*
C29	0.5644 (5)	0.27917 (17)	0.15182 (10)	0.0746 (8)
H29A	0.458457	0.300579	0.172605	0.083 (9)*
H29B	0.491120	0.251580	0.127331	0.069 (8)*
H29C	0.650875	0.330722	0.142003	0.101 (11)*
C30	1.0536 (4)	0.10505 (17)	0.07512 (8)	0.0618 (6)
H30A	1.024791	0.096276	0.044569	0.084 (9)*
H30B	1.090533	0.046459	0.088172	0.082 (8)*
H30C	1.172917	0.147600	0.078635	0.073 (8)*
O3	0.3991 (3)	0.28423 (12)	0.02900 (6)	0.0679 (5)
H31	0.529 (6)	0.261 (3)	0.0381 (12)	0.126 (14)*
H32	0.383 (7)	0.285 (3)	0.0004 (11)	0.134 (16)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0580 (8)	0.0362 (7)	0.0659 (9)	0.0021 (7)	0.0078 (8)	0.0014 (6)
C1	0.0474 (11)	0.0374 (9)	0.0573 (11)	−0.0002 (8)	−0.0029 (10)	0.0039 (8)
C2	0.0708 (15)	0.0385 (11)	0.0855 (17)	−0.0007 (10)	−0.0080 (13)	0.0072 (10)
C3	0.115 (3)	0.0465 (12)	0.0747 (17)	−0.0130 (14)	−0.0051 (17)	−0.0056 (11)
C4	0.108 (2)	0.0514 (13)	0.0678 (15)	−0.0086 (14)	−0.0096 (17)	−0.0090 (11)
C5	0.0506 (11)	0.0425 (10)	0.0543 (11)	0.0002 (9)	−0.0034 (9)	−0.0009 (8)
C6	0.0563 (12)	0.0441 (10)	0.0456 (10)	0.0024 (9)	0.0032 (9)	0.0014 (8)
C7	0.0347 (9)	0.0411 (9)	0.0557 (11)	0.0000 (8)	0.0045 (8)	0.0022 (8)
C8	0.0481 (11)	0.0375 (9)	0.0496 (10)	0.0004 (8)	0.0016 (8)	0.0007 (8)
C9	0.0507 (12)	0.0502 (11)	0.0536 (11)	0.0004 (9)	0.0121 (9)	0.0000 (9)
C10	0.0567 (12)	0.0490 (11)	0.0551 (12)	−0.0076 (10)	0.0046 (10)	0.0090 (9)
C11	0.0424 (10)	0.0434 (10)	0.0676 (13)	0.0065 (8)	−0.0034 (10)	0.0025 (9)
C12	0.166 (4)	0.0473 (13)	0.091 (2)	−0.012 (2)	−0.012 (3)	0.0184 (13)
C13	0.094 (2)	0.0687 (15)	0.0614 (15)	0.0020 (15)	0.0241 (14)	−0.0022 (12)
C14	0.0773 (15)	0.0530 (12)	0.0589 (13)	0.0038 (12)	−0.0102 (12)	0.0096 (10)
C15	0.0757 (17)	0.0549 (12)	0.0625 (13)	−0.0071 (12)	−0.0129 (12)	−0.0032 (11)
O2	0.0531 (8)	0.0519 (8)	0.0647 (9)	−0.0030 (7)	−0.0090 (7)	0.0164 (7)
C16	0.0404 (9)	0.0395 (9)	0.0478 (10)	0.0008 (8)	−0.0035 (8)	0.0029 (8)
C17	0.0542 (12)	0.0513 (11)	0.0525 (11)	−0.0007 (10)	−0.0033 (10)	0.0098 (9)
C18	0.0554 (13)	0.0660 (13)	0.0577 (12)	−0.0060 (11)	0.0031 (11)	0.0126 (11)
C19	0.0577 (13)	0.0645 (13)	0.0608 (13)	0.0043 (11)	0.0112 (11)	0.0007 (11)
C20	0.0410 (10)	0.0475 (10)	0.0532 (11)	0.0025 (9)	0.0015 (9)	0.0024 (8)
C21	0.0561 (12)	0.0402 (9)	0.0623 (13)	0.0023 (9)	0.0049 (11)	−0.0020 (9)
C22	0.0375 (10)	0.0416 (9)	0.0571 (11)	−0.0040 (8)	−0.0036 (9)	0.0018 (8)
C23	0.0444 (10)	0.0433 (10)	0.0513 (11)	0.0020 (8)	−0.0037 (9)	0.0084 (8)
C24	0.0525 (12)	0.0533 (11)	0.0519 (11)	−0.0084 (9)	−0.0092 (10)	0.0043 (9)
C25	0.0565 (12)	0.0429 (10)	0.0529 (11)	−0.0091 (9)	−0.0060 (9)	0.0011 (8)
C26	0.0374 (10)	0.0493 (10)	0.0529 (11)	0.0015 (8)	−0.0054 (9)	0.0032 (8)
C27	0.100 (2)	0.0499 (13)	0.0858 (18)	0.0021 (14)	0.0069 (18)	0.0188 (12)
C28	0.101 (2)	0.0573 (13)	0.0711 (15)	−0.0182 (15)	0.0088 (16)	−0.0150 (13)
C29	0.0770 (17)	0.0526 (13)	0.094 (2)	0.0223 (13)	0.0194 (16)	0.0136 (13)
C30	0.0575 (13)	0.0669 (14)	0.0611 (14)	0.0059 (11)	0.0101 (11)	0.0061 (11)
O3	0.0657 (11)	0.0685 (10)	0.0697 (11)	0.0124 (9)	0.0082 (9)	0.0003 (8)

Geometric parameters (Å, º)

O1—C8	1.451 (2)	O2—H2	0.95 (4)
O1—H1	0.88 (4)	C16—C26	1.531 (3)
C1—C11	1.529 (3)	C16—C25	1.531 (3)
C1—C10	1.531 (3)	C16—C17	1.554 (3)
C1—C5	1.555 (3)	C16—C20	1.555 (3)
C1—C2	1.561 (3)	C17—C18	1.518 (3)
C2—C12	1.496 (4)	C17—C27	1.519 (3)
C2—C3	1.522 (4)	C17—H17	0.9900
C2—H2A	0.9900	C18—C19	1.520 (3)
C3—C4	1.509 (4)	C18—H18A	0.9800
C3—H3A	0.9800	C18—H18B	0.9800
C3—H3B	0.9800	C19—C20	1.535 (3)
C4—C5	1.535 (3)	C19—H19A	0.9800
C4—H4A	0.9800	C19—H19B	0.9800
C4—H4B	0.9800	C20—C21	1.560 (3)
C5—C6	1.558 (3)	C20—H20	0.9900
C5—H5	0.9900	C21—C29	1.524 (3)
C6—C14	1.524 (3)	C21—C28	1.548 (3)
C6—C13	1.539 (3)	C21—C22	1.573 (3)
C6—C7	1.568 (3)	C22—C26	1.540 (3)
C7—C8	1.535 (3)	C22—C23	1.542 (3)
C7—C11	1.536 (3)	C22—H22	0.9900
C7—H7	0.9900	C23—C24	1.525 (3)
C8—C15	1.529 (3)	C23—C30	1.528 (3)
C8—C9	1.531 (3)	C24—C25	1.540 (3)
C9—C10	1.539 (3)	C24—H24A	0.9800
C9—H9A	0.9800	C24—H24B	0.9800
C9—H9B	0.9800	C25—H25A	0.9800
C10—H10A	0.9800	C25—H25B	0.9800
C10—H10B	0.9800	C26—H26A	0.9800
C11—H11A	0.9800	C26—H26B	0.9800
C11—H11B	0.9800	C27—H27A	0.9700
C12—H12A	0.9700	C27—H27B	0.9700
C12—H12B	0.9700	C27—H27C	0.9700
C12—H12C	0.9700	C28—H28A	0.9700
C13—H13A	0.9700	C28—H28B	0.9700
C13—H13B	0.9700	C28—H28C	0.9700
C13—H13C	0.9700	C29—H29A	0.9700
C14—H14A	0.9700	C29—H29B	0.9700
C14—H14B	0.9700	C29—H29C	0.9700
C14—H14C	0.9700	C30—H30A	0.9700
C15—H15A	0.9700	C30—H30B	0.9700
C15—H15B	0.9700	C30—H30C	0.9700
C15—H15C	0.9700	O3—H31	0.91 (3)
O2—C23	1.450 (2)	O3—H32	0.89 (3)
C8—O1—H1	105 (2)	C26—C16—C25	106.92 (16)
C11—C1—C10	107.57 (17)	C26—C16—C17	115.34 (16)
C11—C1—C5	102.62 (17)	C25—C16—C17	115.20 (16)
C10—C1—C5	110.25 (17)	C26—C16—C20	102.76 (15)
C11—C1—C2	114.78 (19)	C25—C16—C20	110.53 (16)
C10—C1—C2	115.40 (19)	C17—C16—C20	105.37 (16)
C5—C1—C2	105.41 (17)	C18—C17—C27	114.9 (2)
C12—C2—C3	113.1 (3)	C18—C17—C16	103.77 (17)
C12—C2—C1	117.6 (2)	C27—C17—C16	117.5 (2)
C3—C2—C1	104.23 (19)	C18—C17—H17	106.7
C12—C2—H2A	107.1	C27—C17—H17	106.7
C3—C2—H2A	107.1	C16—C17—H17	106.7
C1—C2—H2A	107.1	C17—C18—C19	102.99 (19)
C4—C3—C2	104.8 (2)	C17—C18—H18A	111.2
C4—C3—H3A	110.8	C19—C18—H18A	111.2
C2—C3—H3A	110.8	C17—C18—H18B	111.2
C4—C3—H3B	110.8	C19—C18—H18B	111.2
C2—C3—H3B	110.8	H18A—C18—H18B	109.1
H3A—C3—H3B	108.9	C18—C19—C20	102.30 (19)
C3—C4—C5	102.7 (2)	C18—C19—H19A	111.3
C3—C4—H4A	111.2	C20—C19—H19A	111.3
C5—C4—H4A	111.2	C18—C19—H19B	111.3
C3—C4—H4B	111.2	C20—C19—H19B	111.3
C5—C4—H4B	111.2	H19A—C19—H19B	109.2
H4A—C4—H4B	109.1	C19—C20—C16	105.11 (16)
C4—C5—C1	105.71 (18)	C19—C20—C21	121.48 (18)
C4—C5—C6	120.4 (2)	C16—C20—C21	106.71 (16)
C1—C5—C6	106.65 (17)	C19—C20—H20	107.6
C4—C5—H5	107.9	C16—C20—H20	107.6
C1—C5—H5	107.9	C21—C20—H20	107.6
C6—C5—H5	107.9	C29—C21—C28	106.6 (2)
C14—C6—C13	106.06 (19)	C29—C21—C20	111.2 (2)
C14—C6—C5	110.68 (19)	C28—C21—C20	112.24 (19)
C13—C6—C5	113.07 (18)	C29—C21—C22	116.30 (19)
C14—C6—C7	116.49 (17)	C28—C21—C22	108.0 (2)
C13—C6—C7	107.9 (2)	C20—C21—C22	102.63 (15)
C5—C6—C7	102.85 (15)	C26—C22—C23	108.30 (16)
C8—C7—C11	108.41 (16)	C26—C22—C21	100.13 (16)
C8—C7—C6	117.92 (16)	C23—C22—C21	118.34 (17)
C11—C7—C6	100.68 (15)	C26—C22—H22	109.8
C8—C7—H7	109.8	C23—C22—H22	109.8
C11—C7—H7	109.8	C21—C22—H22	109.8
C6—C7—H7	109.8	O2—C23—C24	105.95 (16)
O1—C8—C15	106.67 (16)	O2—C23—C30	105.65 (17)
O1—C8—C9	109.56 (16)	C24—C23—C30	110.69 (18)
C15—C8—C9	110.75 (18)	O2—C23—C22	112.33 (16)
O1—C8—C7	107.79 (15)	C24—C23—C22	111.05 (16)
C15—C8—C7	111.15 (18)	C30—C23—C22	110.95 (18)
C9—C8—C7	110.79 (16)	C23—C24—C25	113.96 (17)
C8—C9—C10	113.53 (18)	C23—C24—H24A	108.8
C8—C9—H9A	108.9	C25—C24—H24A	108.8
C10—C9—H9A	108.9	C23—C24—H24B	108.8
C8—C9—H9B	108.9	C25—C24—H24B	108.8
C10—C9—H9B	108.9	H24A—C24—H24B	107.7
H9A—C9—H9B	107.7	C16—C25—C24	111.74 (16)
C1—C10—C9	111.90 (17)	C16—C25—H25A	109.3
C1—C10—H10A	109.2	C24—C25—H25A	109.3
C9—C10—H10A	109.2	C16—C25—H25B	109.3
C1—C10—H10B	109.2	C24—C25—H25B	109.3
C9—C10—H10B	109.2	H25A—C25—H25B	107.9
H10A—C10—H10B	107.9	C16—C26—C22	101.54 (15)
C1—C11—C7	101.37 (15)	C16—C26—H26A	111.5
C1—C11—H11A	111.5	C22—C26—H26A	111.5
C7—C11—H11A	111.5	C16—C26—H26B	111.5
C1—C11—H11B	111.5	C22—C26—H26B	111.5
C7—C11—H11B	111.5	H26A—C26—H26B	109.3
H11A—C11—H11B	109.3	C17—C27—H27A	109.5
C2—C12—H12A	109.5	C17—C27—H27B	109.5
C2—C12—H12B	109.5	H27A—C27—H27B	109.5
H12A—C12—H12B	109.5	C17—C27—H27C	109.5
C2—C12—H12C	109.5	H27A—C27—H27C	109.5
H12A—C12—H12C	109.5	H27B—C27—H27C	109.5
H12B—C12—H12C	109.5	C21—C28—H28A	109.5
C6—C13—H13A	109.5	C21—C28—H28B	109.5
C6—C13—H13B	109.5	H28A—C28—H28B	109.5
H13A—C13—H13B	109.5	C21—C28—H28C	109.5
C6—C13—H13C	109.5	H28A—C28—H28C	109.5
H13A—C13—H13C	109.5	H28B—C28—H28C	109.5
H13B—C13—H13C	109.5	C21—C29—H29A	109.5
C6—C14—H14A	109.5	C21—C29—H29B	109.5
C6—C14—H14B	109.5	H29A—C29—H29B	109.5
H14A—C14—H14B	109.5	C21—C29—H29C	109.5
C6—C14—H14C	109.5	H29A—C29—H29C	109.5
H14A—C14—H14C	109.5	H29B—C29—H29C	109.5
H14B—C14—H14C	109.5	C23—C30—H30A	109.5
C8—C15—H15A	109.5	C23—C30—H30B	109.5
C8—C15—H15B	109.5	H30A—C30—H30B	109.5
H15A—C15—H15B	109.5	C23—C30—H30C	109.5
C8—C15—H15C	109.5	H30A—C30—H30C	109.5
H15A—C15—H15C	109.5	H30B—C30—H30C	109.5
H15B—C15—H15C	109.5	H31—O3—H32	114 (3)
C23—O2—H2	106 (2)
C11—C1—C2—C12	−107.2 (3)	C26—C16—C17—C18	131.56 (18)
C10—C1—C2—C12	18.8 (4)	C25—C16—C17—C18	−103.1 (2)
C5—C1—C2—C12	140.6 (3)	C20—C16—C17—C18	19.0 (2)
C11—C1—C2—C3	126.7 (2)	C26—C16—C17—C27	−100.4 (3)
C10—C1—C2—C3	−107.4 (2)	C25—C16—C17—C27	25.0 (3)
C5—C1—C2—C3	14.5 (3)	C20—C16—C17—C27	147.1 (2)
C12—C2—C3—C4	−164.1 (3)	C27—C17—C18—C19	−169.6 (2)
C1—C2—C3—C4	−35.3 (3)	C16—C17—C18—C19	−40.0 (2)
C2—C3—C4—C5	42.1 (3)	C17—C18—C19—C20	45.5 (2)
C3—C4—C5—C1	−32.3 (3)	C18—C19—C20—C16	−33.0 (2)
C3—C4—C5—C6	−152.9 (2)	C18—C19—C20—C21	−153.9 (2)
C11—C1—C5—C4	−109.6 (2)	C26—C16—C20—C19	−112.49 (18)
C10—C1—C5—C4	136.0 (2)	C25—C16—C20—C19	133.71 (18)
C2—C1—C5—C4	10.9 (3)	C17—C16—C20—C19	8.7 (2)
C11—C1—C5—C6	19.6 (2)	C26—C16—C20—C21	17.7 (2)
C10—C1—C5—C6	−94.77 (19)	C25—C16—C20—C21	−96.06 (19)
C2—C1—C5—C6	140.07 (19)	C17—C16—C20—C21	138.88 (17)
C4—C5—C6—C14	−103.4 (2)	C19—C20—C21—C29	−101.4 (2)
C1—C5—C6—C14	136.37 (18)	C16—C20—C21—C29	138.5 (2)
C4—C5—C6—C13	15.4 (3)	C19—C20—C21—C28	18.0 (3)
C1—C5—C6—C13	−104.8 (2)	C16—C20—C21—C28	−102.2 (2)
C4—C5—C6—C7	131.5 (2)	C19—C20—C21—C22	133.6 (2)
C1—C5—C6—C7	11.3 (2)	C16—C20—C21—C22	13.4 (2)
C14—C6—C7—C8	−41.3 (3)	C29—C21—C22—C26	−160.8 (2)
C13—C6—C7—C8	−160.33 (18)	C28—C21—C22—C26	79.5 (2)
C5—C6—C7—C8	79.94 (19)	C20—C21—C22—C26	−39.21 (19)
C14—C6—C7—C11	−158.90 (19)	C29—C21—C22—C23	−43.5 (3)
C13—C6—C7—C11	82.0 (2)	C28—C21—C22—C23	−163.19 (18)
C5—C6—C7—C11	−37.69 (18)	C20—C21—C22—C23	78.1 (2)
C11—C7—C8—O1	179.71 (16)	C26—C22—C23—O2	176.92 (16)
C6—C7—C8—O1	66.3 (2)	C21—C22—C23—O2	64.0 (2)
C11—C7—C8—C15	−63.7 (2)	C26—C22—C23—C24	58.5 (2)
C6—C7—C8—C15	−177.15 (17)	C21—C22—C23—C24	−54.4 (2)
C11—C7—C8—C9	59.8 (2)	C26—C22—C23—C30	−65.1 (2)
C6—C7—C8—C9	−53.6 (2)	C21—C22—C23—C30	−177.95 (17)
O1—C8—C9—C10	−162.39 (17)	O2—C23—C24—C25	−164.97 (18)
C15—C8—C9—C10	80.2 (2)	C30—C23—C24—C25	81.0 (2)
C7—C8—C9—C10	−43.6 (2)	C22—C23—C24—C25	−42.7 (2)
C11—C1—C10—C9	−59.7 (2)	C26—C16—C25—C24	−60.4 (2)
C5—C1—C10—C9	51.5 (2)	C17—C16—C25—C24	169.95 (18)
C2—C1—C10—C9	170.8 (2)	C20—C16—C25—C24	50.7 (2)
C8—C9—C10—C1	44.0 (3)	C23—C24—C25—C16	44.2 (3)
C10—C1—C11—C7	72.7 (2)	C25—C16—C26—C22	73.57 (18)
C5—C1—C11—C7	−43.6 (2)	C17—C16—C26—C22	−156.90 (17)
C2—C1—C11—C7	−157.35 (19)	C20—C16—C26—C22	−42.83 (19)
C8—C7—C11—C1	−73.5 (2)	C23—C22—C26—C16	−73.22 (19)
C6—C7—C11—C1	50.9 (2)	C21—C22—C26—C16	51.31 (18)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O3	0.88 (4)	1.93 (4)	2.795 (2)	167 (3)
O2—H2···O1^i	0.95 (4)	1.87 (4)	2.810 (2)	168 (3)
O3—H31···O2	0.91 (3)	2.00 (3)	2.897 (3)	166 (4)
O3—H32···O2^ii	0.89 (3)	2.30 (3)	3.185 (3)	171 (4)

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