2,4-Bis[1-(4-hydroxy­phen­yl)-1-methyl­ethyl]phenol: a three-dimensional framework built from O—H...O hydrogen bonds

In the crystal structure of the title compound, C₂₄H₂₆O₃, (I), there are three different O—H...O hydrogen bonds, which individually form chains of C(10), C(12) and C(16) types. The combined effect of all these hydrogen bonds is the formation of a three-dimensional network, which is additionally stabilized by a single inter­molecular C—H...π inter­action. The significance of this study lies in the comparison drawn between the mol­ecular structure of (I) and those of several of its analogues, which shows a close similarity in the almost perpendicular orientation of the benzene rings.

S1. Comment

The present investigation of the title compound, (I), is a continuation of our work on the structural study of compounds formed as by-products during the industrial production of 4,4'-isopropylidenediphenol, (II) (commonly referred to as bisphenol-A or p,p-BPA). In previous papers, the structures of two such by-products, i.e. 2,4'-isopropylidenediphenol, (III) [o,p-BPA; Cambridge Structural Database (CSD; Allen, 2002) refcode GALCAY (Rozycka-Sokolowska et al., 2005)], and 2,2'-isopropylidenediphenol, (IV) [o,o-BPA; CSD refcode UCOFIC (Rozycka-Sokolowska et al. 2006)], were reported. Now, the structure of a third by-product, (I), i.e. 2,4-bis[1-(4-hydroxyphenyl)-1-methylethyl]phenol (commonly referred to as BPX-1), is reported. We note that the 2,4-bis(α,α-dimethylbenzyl)phenol skeleton also occurs in WOBROU, (V) (Bryan, 2000), and VACKUF, (VI) (Kurashev et al., 1986)], while (I) may be treated as a (4-hydroxyphenyl)isopropyl derivative of p,p-BPA, (II) (CEGYOC02; Okada, 1996), or of o,p-BPA, (III), sharing structural features with these two isomers of BPA.

Compound (I) is constructed around a benzene ring (C10–C15), which has (4-hydroxyphenyl)isopropyl substituents at positions 2 and 4 and a hydroxy substituent at position 1 (Fig. 1). This ring and the two benzene rings belonging to the former substituents, i.e. the C1–C6 and C19–C24 rings, are planar, with largest deviations from planarity of -0.008 (2), 0.013 (2) and 0.011 (2) Å for atoms C4, C11 and C22, respectively. Similarly to the case of the three isomers of isopropylidenediphenol, each hydroxy O atom attached to the benzene ring is nearly coplanar with it. Namely, atom O22 lies only 0.017 (2) Å above the plane of the C19–C24 ring, whereas atoms O1 and O11 lie 0.037 (2) and 0.001 (2) Å below the planes formed by atoms C1–C6 and C10–C15, respectively. The dihedral angles between the least-squares plane defined by the C atoms of the central benzene ring (C10–C15) and the C1–C6 and C19–C24 planes are 87.2 (1) and 82.4 (1)°, respectively, while the latter two planes are inclined at 82.8 (1)° to one another. As can be seen in Fig. 1, there is one weak intramolecular C—H···O hydrogen bond, which links the methyl atom C8, via H8A, with the hydroxy atom O11 and generates an S(6) graph-set motif (Bernstein et al., 1995). The non-coplanar practically perpendicular orientation of the benzene rings belonging to the molecule of (I), and the presence of an intramolecular C—H···O hydrogen bond with such a graph-set descriptor, are in agreement with the structures observed for compounds (III)–(VI).

The crystal structure of (I) contains three strong, nearly linear O—H···O hydrogen bonds (Table 1), which connect each molecule to six others. These interactions result in the formation of a continuous three-dimensional framework, which can be analysed in terms of three independent one-dimensional substructures, each generated by one of the O—H···O hydrogen bonds.

In the first substructure, atom O1 in the molecule at (x, y, z) acts as a hydrogen-bond donor, via H1, to atom O11 belonging to the molecule at (x + 1/2, y - 1/2, z), so forming a C(10) chain running parallel to the [110] direction (Fig. 2). Two chains of this type pass through each unit cell, parallel to [110] and [110], where the component molecules are related by the c-glide plane at y = 1/2. In the second substructure, hydroxy atom O11 acts as a hydrogen bond donor, via H11, to atom O22 belonging to the molecule at (x + 1/2, -y + 1/2, z + 1/2), so forming a zigzag C(12) chain (Fig. 3), which runs parallel to the [101] direction and is built from molecules related by the c-glide plane at y = 1/4. The third substructure is generated by the O—H···O hydrogen bond that links hydroxy atom O22 at (x, y, z), via H22, with hydroxy atom O1 belonging to the molecule at (x, -y, z - 1/2), so generating a zigzag C(16) chain (Fig. 4). This chain runs along the [001] direction and comprises molecules related by the c-glide plane at y = 0. Two parallel C(12) and two parallel C(16) chains pass through each unit cell.

The combined effect of the C(10), C(12) and C(16) chains parallel to the [110] and [110], [101], and [001] directions, respectively, is sufficient to generate the continuous three-dimensional network. This network is additionally stabilized by a weak C—H···π interaction, which connects aromatic atom C12 at (x, y, z), via atom H12, with the centroid of the C1–C6 benzene ring (Cg1) of the molecule at (x + 1/2, y + 1/2, z) (Fig. 5).

Related literature

For related literature, see: Bernstein et al. (1995); Bryan (2000); Kurashev et al. (1986); Okada (1996); Rozycka-Sokolowska, Marciniak & Pavlyuk (2006); Rozycka-Sokolowska, Marciniak, Pavlyuk & Dziwinski (2005).

S2. Experimental

A crystal of (I) [or Crystals of (I)?] suitable for X-ray diffraction measurement was obtained from solution by slow evaporation of ethanol used as a solvent at a constant temperature of 279 K.

S3. Refinement

All aromatic H atoms were positioned geometrically and constrained to ride on their parent atoms, with C—H distances of 0.93 Å and with U_iso(H) values of 1.2U_eq(C). H atoms of hydroxy and methyl groups were located in difference maps and refined isotropically, giving O—H distances in the range 0.87 (4)–0.92 (3) Å and C—H distances of 0.94 (4)–1.03 (4) Å. In the absence of significant resonant scattering, the Flack (1983) parameter was indeterminate (Flack & Bernardinelli, 2000), and the Friedel equivalent reflections were merged prior to the final refinement.

Computing details

Data collection: CrysAlis CCD (Oxford Diffraction, 2004); cell refinement: CrysAlis RED (Oxford Diffraction, 2005); data reduction: CrysAlis RED (Oxford Diffraction, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek,2003) and DIAMOND (Brandenburg, 2006); software used to prepare material for publication: publCIF (Westrip, 2008).

Figures

	Fig. 1. A view of the molecule of (I), showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 40% probability level. The dashed line depicts the intramolecular hydrogen bond forming a pattern with the S(6) descriptor. H atoms as drawn as spheres of arbitrary radii.
	Fig. 2. Part of the crystal structure of (I), showing the formation of two antiparallel hydrogen-bonded C(10) chains along the [110] and [110] directions. The C atoms of methyl groups and all H atoms not involved in the motifs have been omitted for clarity. [Symmetry codes: (i) x + 1/2, y - 1/2, z; (v) x - 1/2, y + 1/2, z; (vi) x - 1, -y, z + 1/2; (vii) x - 1/2, -y + 1/2, z + 1/2; (viii) x, 1 - y, z + 1/2.]
	Fig. 3. Part of the crystal structure of (I), showing the formation of two parallel hydrogen-bonded C(12) chains along the [101] direction. The C atoms of methyl groups and all H atoms not involved in the motifs have been omitted for clarity. [Symmetry codes: (ii) x + 1/2, -y + 1/2, z + 1/2; (iv) x + 1/2, y + 1/2, z; (ix) x - 1/2, -y + 1/2, z - 1/2; (x) x, -y + 1, z - 1/2; (xi) x + 1, -y + 1, z + 1/2.]
	Fig. 4. Part of the crystal structure of (I), showing the formation of two parallel hydrogen-bonded C(16) chains along the [001] direction. The C atoms of methyl groups and all H atoms not involved in the motifs have been omitted for clarity. [Symmetry codes: (ii) x + 1/2, -y + 1/2, z + 1/2; (iii) x, -y, z - 1/2; (iv) x + 1/2, y + 1/2, z; (xii) x, -y, z + 1/2; (xiii) x + 1/2, -y + 1/2, z - 1/2.]
	Fig. 5. Part of the crystal structure of (I), showing the intermolecular C—H···π interaction. The C atoms of methyl groups and all H atoms not involved in this interaction have been omitted for clarity. [Symmetry codes: (iv) x + 1/2, y + 1/2, z; (xiv) x - 1/2, y - 1/2, z.]

2,4-Bis[1-(4-hydroxyphenyl)-1-methylethyl]phenol

Crystal data

C24H26O3	F(000) = 776
Mr = 362.45	Dx = 1.217 Mg m^−3
Monoclinic, Cc	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C -2yc	Cell parameters from 7160 reflections
a = 6.2143 (2) Å	θ = 3.7–28.5°
b = 15.3978 (5) Å	µ = 0.08 mm^−1
c = 20.7130 (7) Å	T = 290 K
β = 93.729 (3)°	Plate, colourless
V = 1977.76 (11) Å^3	0.30 × 0.27 × 0.07 mm
Z = 4

Data collection

Oxford Diffraction Xcalibur3 CCD diffractometer	1729 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.027
Graphite monochromator	θmax = 28.5°, θmin = 3.7°
ω scans	h = −4→8
7160 measured reflections	k = −20→20
2469 independent reflections	l = −27→27

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.033	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.082	w = 1/[σ^2(Fo^2) + (0.037P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.08	(Δ/σ)max < 0.001
2469 reflections	Δρmax = 0.12 e Å^−3
305 parameters	Δρmin = −0.11 e Å^−3
2 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0061 (10)

Special details

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	0.5406 (3)	−0.02012 (11)	0.37253 (9)	0.0444 (5)
H1	0.644 (5)	−0.0497 (19)	0.3517 (14)	0.046 (8)*
O11	0.3346 (3)	0.36520 (12)	0.31969 (9)	0.0421 (5)
H11	0.452 (6)	0.368 (2)	0.3444 (19)	0.082 (12)*
O22	0.2115 (3)	0.13003 (13)	−0.09752 (9)	0.0493 (5)
H22	0.324 (6)	0.095 (2)	−0.1009 (17)	0.073 (11)*
C1	0.4471 (4)	0.04760 (14)	0.33657 (12)	0.0341 (5)
C2	0.2680 (4)	0.08643 (15)	0.35965 (12)	0.0370 (6)
H2	0.2163	0.0678	0.3984	0.044*
C3	0.1646 (4)	0.15324 (16)	0.32527 (12)	0.0373 (6)
H3	0.0440	0.1790	0.3415	0.045*
C4	0.2362 (4)	0.18258 (15)	0.26741 (11)	0.0322 (5)
C5	0.4198 (4)	0.14290 (16)	0.24596 (12)	0.0379 (6)
H5	0.4735	0.1620	0.2076	0.046*
C6	0.5253 (4)	0.07605 (16)	0.27973 (13)	0.0410 (6)
H6	0.6475	0.0507	0.2641	0.049*
C7	0.1159 (4)	0.25118 (16)	0.22496 (12)	0.0353 (6)
C8	−0.0735 (5)	0.2919 (2)	0.25791 (18)	0.0512 (7)
H8A	−0.018 (5)	0.319 (2)	0.3016 (16)	0.055 (8)*
H8B	−0.142 (6)	0.336 (2)	0.2310 (17)	0.069 (10)*
H8C	−0.179 (5)	0.249 (2)	0.2671 (13)	0.051 (8)*
C9	0.0197 (5)	0.2034 (2)	0.16419 (16)	0.0490 (7)
H9A	−0.071 (5)	0.155 (2)	0.1803 (15)	0.061 (9)*
H9B	−0.055 (5)	0.249 (2)	0.1370 (15)	0.057 (8)*
H9C	0.139 (7)	0.176 (3)	0.1388 (19)	0.085 (12)*
C10	0.2722 (3)	0.32353 (15)	0.20750 (11)	0.0319 (5)
C11	0.3749 (3)	0.37685 (16)	0.25467 (11)	0.0324 (5)
C12	0.5089 (4)	0.44322 (16)	0.23846 (12)	0.0372 (6)
H12	0.5710	0.4790	0.2707	0.045*
C13	0.5527 (4)	0.45744 (16)	0.17467 (11)	0.0350 (6)
H13	0.6452	0.5021	0.1645	0.042*
C14	0.4591 (4)	0.40529 (15)	0.12558 (11)	0.0328 (5)
C15	0.3191 (4)	0.34027 (15)	0.14352 (12)	0.0338 (5)
H15	0.2529	0.3060	0.1111	0.041*
C16	0.5051 (4)	0.42310 (17)	0.05480 (12)	0.0388 (6)
C17	0.3854 (7)	0.5065 (2)	0.03364 (18)	0.0584 (9)
H17A	0.226 (5)	0.5046 (19)	0.0364 (13)	0.051 (8)*
H17B	0.434 (5)	0.557 (2)	0.0574 (16)	0.063 (9)*
H17C	0.414 (6)	0.515 (3)	−0.010 (2)	0.092 (13)*
C18	0.7485 (6)	0.4386 (3)	0.05002 (17)	0.0613 (9)
H18A	0.786 (6)	0.445 (2)	0.005 (2)	0.077 (10)*
H18B	0.803 (6)	0.491 (3)	0.0760 (18)	0.081 (11)*
H18C	0.838 (7)	0.393 (3)	0.068 (2)	0.095 (14)*
C19	0.4320 (4)	0.34605 (16)	0.01130 (11)	0.0360 (6)
C20	0.2422 (4)	0.34647 (18)	−0.02746 (13)	0.0452 (7)
H20	0.1594	0.3968	−0.0294	0.054*
C21	0.1703 (4)	0.27551 (17)	−0.06331 (14)	0.0482 (7)
H21	0.0417	0.2786	−0.0888	0.058*
C22	0.2888 (4)	0.20039 (17)	−0.06122 (12)	0.0385 (6)
C23	0.4811 (5)	0.1982 (2)	−0.02430 (15)	0.0580 (8)
H23	0.5651	0.1482	−0.0232	0.070*
C24	0.5490 (5)	0.2701 (2)	0.01098 (15)	0.0579 (8)
H24	0.6794	0.2672	0.0356	0.070*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0530 (11)	0.0345 (10)	0.0450 (11)	0.0063 (9)	−0.0027 (9)	0.0064 (8)
O11	0.0441 (10)	0.0495 (11)	0.0321 (10)	−0.0020 (8)	−0.0023 (8)	−0.0019 (8)
O22	0.0548 (12)	0.0431 (11)	0.0489 (12)	0.0019 (9)	−0.0059 (9)	−0.0106 (9)
C1	0.0405 (13)	0.0263 (12)	0.0345 (13)	−0.0018 (10)	−0.0037 (10)	0.0020 (10)
C2	0.0509 (15)	0.0328 (13)	0.0271 (13)	−0.0017 (11)	0.0017 (10)	−0.0003 (10)
C3	0.0426 (14)	0.0335 (14)	0.0362 (14)	0.0038 (11)	0.0063 (10)	−0.0046 (11)
C4	0.0331 (12)	0.0296 (13)	0.0335 (13)	−0.0002 (10)	−0.0004 (9)	−0.0001 (10)
C5	0.0376 (13)	0.0376 (14)	0.0391 (14)	0.0015 (11)	0.0060 (10)	0.0084 (11)
C6	0.0361 (13)	0.0380 (15)	0.0495 (16)	0.0062 (11)	0.0079 (11)	0.0046 (12)
C7	0.0352 (12)	0.0307 (14)	0.0390 (14)	0.0014 (9)	−0.0058 (10)	0.0029 (10)
C8	0.0333 (14)	0.0453 (17)	0.075 (2)	0.0061 (14)	0.0015 (14)	0.0054 (17)
C9	0.0514 (18)	0.0419 (17)	0.0512 (18)	−0.0119 (14)	−0.0163 (14)	0.0066 (14)
C10	0.0349 (12)	0.0262 (12)	0.0337 (13)	0.0054 (10)	−0.0036 (10)	−0.0009 (10)
C11	0.0316 (12)	0.0353 (14)	0.0297 (13)	0.0039 (10)	−0.0025 (9)	−0.0027 (10)
C12	0.0405 (13)	0.0354 (14)	0.0347 (14)	0.0013 (10)	−0.0047 (10)	−0.0077 (10)
C13	0.0377 (12)	0.0306 (13)	0.0364 (15)	−0.0061 (10)	−0.0006 (10)	−0.0046 (11)
C14	0.0354 (12)	0.0311 (13)	0.0313 (13)	0.0046 (10)	−0.0025 (9)	−0.0015 (10)
C15	0.0364 (13)	0.0289 (13)	0.0350 (13)	−0.0008 (9)	−0.0055 (10)	−0.0025 (10)
C16	0.0462 (14)	0.0404 (15)	0.0289 (13)	−0.0047 (11)	−0.0048 (10)	0.0010 (10)
C17	0.089 (3)	0.0381 (17)	0.0461 (19)	0.0001 (17)	−0.0117 (17)	0.0037 (14)
C18	0.058 (2)	0.086 (3)	0.041 (2)	−0.0192 (19)	0.0080 (15)	−0.0067 (17)
C19	0.0414 (13)	0.0396 (14)	0.0265 (12)	0.0028 (11)	−0.0012 (10)	0.0007 (10)
C20	0.0431 (14)	0.0429 (16)	0.0484 (16)	0.0109 (12)	−0.0076 (12)	−0.0067 (12)
C21	0.0393 (14)	0.0483 (17)	0.0543 (17)	0.0098 (12)	−0.0161 (12)	−0.0097 (13)
C22	0.0462 (14)	0.0384 (15)	0.0307 (13)	0.0002 (11)	0.0010 (10)	−0.0050 (11)
C23	0.0616 (18)	0.0461 (17)	0.063 (2)	0.0259 (14)	−0.0187 (15)	−0.0146 (14)
C24	0.0597 (17)	0.0546 (18)	0.0556 (18)	0.0137 (14)	−0.0270 (14)	−0.0161 (14)

Geometric parameters (Å, º)

O1—C1	1.387 (3)	C11—C12	1.374 (3)
O1—H1	0.92 (3)	C12—C13	1.384 (3)
O11—C11	1.397 (3)	C12—H12	0.9300
O11—H11	0.87 (4)	C13—C14	1.393 (3)
O22—C22	1.386 (3)	C13—H13	0.9300
O22—H22	0.89 (4)	C14—C15	1.393 (3)
C1—C6	1.374 (4)	C14—C16	1.536 (3)
C1—C2	1.376 (3)	C15—H15	0.9300
C2—C3	1.385 (3)	C16—C17	1.534 (4)
C2—H2	0.9300	C16—C19	1.540 (3)
C3—C4	1.381 (3)	C16—C18	1.541 (4)
C3—H3	0.9300	C17—H17A	0.99 (3)
C4—C5	1.392 (3)	C17—H17B	0.95 (3)
C4—C7	1.537 (3)	C17—H17C	0.94 (4)
C5—C6	1.385 (3)	C18—H18A	0.98 (4)
C5—H5	0.9300	C18—H18B	1.01 (4)
C6—H6	0.9300	C18—H18C	0.96 (4)
C7—C8	1.532 (4)	C19—C24	1.377 (4)
C7—C10	1.537 (3)	C19—C20	1.383 (3)
C7—C9	1.545 (4)	C20—C21	1.379 (4)
C8—H8A	1.03 (3)	C20—H20	0.9300
C8—H8B	0.96 (4)	C21—C22	1.370 (4)
C8—H8C	0.96 (3)	C21—H21	0.9300
C9—H9A	1.00 (3)	C22—C23	1.377 (4)
C9—H9B	1.00 (3)	C23—C24	1.378 (4)
C9—H9C	1.03 (4)	C23—H23	0.9300
C10—C11	1.398 (3)	C24—H24	0.9300
C10—C15	1.399 (3)
C1—O1—H1	113.7 (17)	C13—C12—H12	119.6
C11—O11—H11	111 (3)	C12—C13—C14	120.5 (2)
C22—O22—H22	106 (2)	C12—C13—H13	119.8
C6—C1—C2	119.9 (2)	C14—C13—H13	119.8
C6—C1—O1	122.8 (2)	C15—C14—C13	117.3 (2)
C2—C1—O1	117.4 (2)	C15—C14—C16	122.8 (2)
C1—C2—C3	120.2 (2)	C13—C14—C16	119.9 (2)
C1—C2—H2	119.9	C14—C15—C10	123.9 (2)
C3—C2—H2	119.9	C14—C15—H15	118.1
C4—C3—C2	121.6 (2)	C10—C15—H15	118.1
C4—C3—H3	119.2	C17—C16—C14	107.8 (2)
C2—C3—H3	119.2	C17—C16—C19	111.0 (2)
C3—C4—C5	116.8 (2)	C14—C16—C19	110.8 (2)
C3—C4—C7	123.3 (2)	C17—C16—C18	108.1 (3)
C5—C4—C7	119.8 (2)	C14—C16—C18	109.5 (2)
C6—C5—C4	122.4 (2)	C19—C16—C18	109.6 (2)
C6—C5—H5	118.8	C16—C17—H17A	115.1 (17)
C4—C5—H5	118.8	C16—C17—H17B	113.5 (19)
C1—C6—C5	119.2 (2)	H17A—C17—H17B	106 (3)
C1—C6—H6	120.4	C16—C17—H17C	106 (2)
C5—C6—H6	120.4	H17A—C17—H17C	108 (3)
C8—C7—C10	108.9 (2)	H17B—C17—H17C	108 (3)
C8—C7—C4	112.7 (2)	C16—C18—H18A	112 (2)
C10—C7—C4	109.96 (18)	C16—C18—H18B	113 (2)
C8—C7—C9	106.9 (2)	H18A—C18—H18B	110 (3)
C10—C7—C9	111.8 (2)	C16—C18—H18C	114 (2)
C4—C7—C9	106.7 (2)	H18A—C18—H18C	106 (3)
C7—C8—H8A	109.5 (17)	H18B—C18—H18C	102 (3)
C7—C8—H8B	111 (2)	C24—C19—C20	115.6 (2)
H8A—C8—H8B	110 (3)	C24—C19—C16	121.4 (2)
C7—C8—H8C	111.2 (17)	C20—C19—C16	122.9 (2)
H8A—C8—H8C	107 (2)	C21—C20—C19	122.9 (2)
H8B—C8—H8C	108 (3)	C21—C20—H20	118.6
C7—C9—H9A	106.0 (18)	C19—C20—H20	118.6
C7—C9—H9B	105.3 (18)	C22—C21—C20	119.8 (2)
H9A—C9—H9B	117 (3)	C22—C21—H21	120.1
C7—C9—H9C	111 (2)	C20—C21—H21	120.1
H9A—C9—H9C	108 (3)	C21—C22—C23	118.9 (2)
H9B—C9—H9C	109 (3)	C21—C22—O22	118.4 (2)
C11—C10—C15	116.1 (2)	C23—C22—O22	122.6 (2)
C11—C10—C7	121.9 (2)	C22—C23—C24	120.0 (2)
C15—C10—C7	122.0 (2)	C22—C23—H23	120.0
C12—C11—O11	118.7 (2)	C24—C23—H23	120.0
C12—C11—C10	121.5 (2)	C19—C24—C23	122.8 (2)
O11—C11—C10	119.7 (2)	C19—C24—H24	118.6
C11—C12—C13	120.7 (2)	C23—C24—H24	118.6
C11—C12—H12	119.6
C6—C1—C2—C3	0.9 (3)	C12—C13—C14—C15	1.0 (3)
O1—C1—C2—C3	−178.7 (2)	C12—C13—C14—C16	178.6 (2)
C1—C2—C3—C4	0.2 (3)	C13—C14—C15—C10	−1.6 (3)
C2—C3—C4—C5	−1.2 (3)	C16—C14—C15—C10	−179.1 (2)
C2—C3—C4—C7	174.8 (2)	C11—C10—C15—C14	0.2 (3)
C3—C4—C5—C6	1.2 (3)	C7—C10—C15—C14	179.8 (2)
C7—C4—C5—C6	−175.0 (2)	C15—C14—C16—C17	105.4 (3)
C2—C1—C6—C5	−0.9 (4)	C13—C14—C16—C17	−72.0 (3)
O1—C1—C6—C5	178.6 (2)	C15—C14—C16—C19	−16.2 (3)
C4—C5—C6—C1	−0.1 (4)	C13—C14—C16—C19	166.3 (2)
C3—C4—C7—C8	7.7 (3)	C15—C14—C16—C18	−137.2 (3)
C5—C4—C7—C8	−176.4 (2)	C13—C14—C16—C18	45.4 (3)
C3—C4—C7—C10	129.4 (2)	C17—C16—C19—C24	164.9 (3)
C5—C4—C7—C10	−54.8 (3)	C14—C16—C19—C24	−75.4 (3)
C3—C4—C7—C9	−109.3 (3)	C18—C16—C19—C24	45.5 (4)
C5—C4—C7—C9	66.6 (3)	C17—C16—C19—C20	−18.2 (4)
C8—C7—C10—C11	60.7 (3)	C14—C16—C19—C20	101.6 (3)
C4—C7—C10—C11	−63.2 (3)	C18—C16—C19—C20	−137.5 (3)
C9—C7—C10—C11	178.5 (2)	C24—C19—C20—C21	1.3 (4)
C8—C7—C10—C15	−118.9 (3)	C16—C19—C20—C21	−175.9 (3)
C4—C7—C10—C15	117.2 (2)	C19—C20—C21—C22	0.2 (5)
C9—C7—C10—C15	−1.1 (3)	C20—C21—C22—C23	−1.6 (4)
C15—C10—C11—C12	1.8 (3)	C20—C21—C22—O22	179.6 (3)
C7—C10—C11—C12	−177.8 (2)	C21—C22—C23—C24	1.5 (5)
C15—C10—C11—O11	179.1 (2)	O22—C22—C23—C24	−179.7 (3)
C7—C10—C11—O11	−0.5 (3)	C20—C19—C24—C23	−1.3 (4)
O11—C11—C12—C13	−179.7 (2)	C16—C19—C24—C23	175.9 (3)
C10—C11—C12—C13	−2.3 (3)	C22—C23—C24—C19	0.0 (5)
C11—C12—C13—C14	0.8 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O11^i	0.92 (3)	1.91 (3)	2.813 (3)	166 (3)
O11—H11···O22^ii	0.87 (4)	1.95 (4)	2.813 (3)	177 (4)
O22—H22···O1^iii	0.89 (4)	1.88 (4)	2.756 (3)	167 (3)
C8—H8A···O11	1.03 (3)	2.31 (3)	2.987 (4)	122 (2)
C12—H12···Cg1^iv	0.93	2.74	3.564 (3)	148

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