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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.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270108006045/gd3195sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270108006045/gd3195Isup2.hkl
Contains datablock I

CCDC reference: 686452

Comment top

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 top

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).

Experimental top

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.

Refinement top

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 Uiso(H) values of 1.2Ueq(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 top

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 top
[Figure 1] 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.
[Figure 2] 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.]
[Figure 3] 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.]
[Figure 4] 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.]
[Figure 5] 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 top
Crystal data top
C24H26O3F(000) = 776
Mr = 362.45Dx = 1.217 Mg m3
Monoclinic, CcMo Kα radiation, λ = 0.71073 Å
Hall symbol: C -2ycCell parameters from 7160 reflections
a = 6.2143 (2) Åθ = 3.7–28.5°
b = 15.3978 (5) ŵ = 0.08 mm1
c = 20.7130 (7) ÅT = 290 K
β = 93.729 (3)°Plate, colourless
V = 1977.76 (11) Å30.30 × 0.27 × 0.07 mm
Z = 4
Data collection top
Oxford Diffraction Xcalibur3 CCD
diffractometer
1729 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.027
Graphite monochromatorθmax = 28.5°, θmin = 3.7°
ω scansh = 48
7160 measured reflectionsk = 2020
2469 independent reflectionsl = 2727
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.033H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.082 w = 1/[σ2(Fo2) + (0.037P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.08(Δ/σ)max < 0.001
2469 reflectionsΔρmax = 0.12 e Å3
305 parametersΔρmin = 0.11 e Å3
2 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0061 (10)
Crystal data top
C24H26O3V = 1977.76 (11) Å3
Mr = 362.45Z = 4
Monoclinic, CcMo Kα radiation
a = 6.2143 (2) ŵ = 0.08 mm1
b = 15.3978 (5) ÅT = 290 K
c = 20.7130 (7) Å0.30 × 0.27 × 0.07 mm
β = 93.729 (3)°
Data collection top
Oxford Diffraction Xcalibur3 CCD
diffractometer
1729 reflections with I > 2σ(I)
7160 measured reflectionsRint = 0.027
2469 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0332 restraints
wR(F2) = 0.082H atoms treated by a mixture of independent and constrained refinement
S = 1.08Δρmax = 0.12 e Å3
2469 reflectionsΔρmin = 0.11 e Å3
305 parameters
Special details top

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 (Å2) top
xyzUiso*/Ueq
O10.5406 (3)0.02012 (11)0.37253 (9)0.0444 (5)
H10.644 (5)0.0497 (19)0.3517 (14)0.046 (8)*
O110.3346 (3)0.36520 (12)0.31969 (9)0.0421 (5)
H110.452 (6)0.368 (2)0.3444 (19)0.082 (12)*
O220.2115 (3)0.13003 (13)0.09752 (9)0.0493 (5)
H220.324 (6)0.095 (2)0.1009 (17)0.073 (11)*
C10.4471 (4)0.04760 (14)0.33657 (12)0.0341 (5)
C20.2680 (4)0.08643 (15)0.35965 (12)0.0370 (6)
H20.21630.06780.39840.044*
C30.1646 (4)0.15324 (16)0.32527 (12)0.0373 (6)
H30.04400.17900.34150.045*
C40.2362 (4)0.18258 (15)0.26741 (11)0.0322 (5)
C50.4198 (4)0.14290 (16)0.24596 (12)0.0379 (6)
H50.47350.16200.20760.046*
C60.5253 (4)0.07605 (16)0.27973 (13)0.0410 (6)
H60.64750.05070.26410.049*
C70.1159 (4)0.25118 (16)0.22496 (12)0.0353 (6)
C80.0735 (5)0.2919 (2)0.25791 (18)0.0512 (7)
H8A0.018 (5)0.319 (2)0.3016 (16)0.055 (8)*
H8B0.142 (6)0.336 (2)0.2310 (17)0.069 (10)*
H8C0.179 (5)0.249 (2)0.2671 (13)0.051 (8)*
C90.0197 (5)0.2034 (2)0.16419 (16)0.0490 (7)
H9A0.071 (5)0.155 (2)0.1803 (15)0.061 (9)*
H9B0.055 (5)0.249 (2)0.1370 (15)0.057 (8)*
H9C0.139 (7)0.176 (3)0.1388 (19)0.085 (12)*
C100.2722 (3)0.32353 (15)0.20750 (11)0.0319 (5)
C110.3749 (3)0.37685 (16)0.25467 (11)0.0324 (5)
C120.5089 (4)0.44322 (16)0.23846 (12)0.0372 (6)
H120.57100.47900.27070.045*
C130.5527 (4)0.45744 (16)0.17467 (11)0.0350 (6)
H130.64520.50210.16450.042*
C140.4591 (4)0.40529 (15)0.12558 (11)0.0328 (5)
C150.3191 (4)0.34027 (15)0.14352 (12)0.0338 (5)
H150.25290.30600.11110.041*
C160.5051 (4)0.42310 (17)0.05480 (12)0.0388 (6)
C170.3854 (7)0.5065 (2)0.03364 (18)0.0584 (9)
H17A0.226 (5)0.5046 (19)0.0364 (13)0.051 (8)*
H17B0.434 (5)0.557 (2)0.0574 (16)0.063 (9)*
H17C0.414 (6)0.515 (3)0.010 (2)0.092 (13)*
C180.7485 (6)0.4386 (3)0.05002 (17)0.0613 (9)
H18A0.786 (6)0.445 (2)0.005 (2)0.077 (10)*
H18B0.803 (6)0.491 (3)0.0760 (18)0.081 (11)*
H18C0.838 (7)0.393 (3)0.068 (2)0.095 (14)*
C190.4320 (4)0.34605 (16)0.01130 (11)0.0360 (6)
C200.2422 (4)0.34647 (18)0.02746 (13)0.0452 (7)
H200.15940.39680.02940.054*
C210.1703 (4)0.27551 (17)0.06331 (14)0.0482 (7)
H210.04170.27860.08880.058*
C220.2888 (4)0.20039 (17)0.06122 (12)0.0385 (6)
C230.4811 (5)0.1982 (2)0.02430 (15)0.0580 (8)
H230.56510.14820.02320.070*
C240.5490 (5)0.2701 (2)0.01098 (15)0.0579 (8)
H240.67940.26720.03560.070*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0530 (11)0.0345 (10)0.0450 (11)0.0063 (9)0.0027 (9)0.0064 (8)
O110.0441 (10)0.0495 (11)0.0321 (10)0.0020 (8)0.0023 (8)0.0019 (8)
O220.0548 (12)0.0431 (11)0.0489 (12)0.0019 (9)0.0059 (9)0.0106 (9)
C10.0405 (13)0.0263 (12)0.0345 (13)0.0018 (10)0.0037 (10)0.0020 (10)
C20.0509 (15)0.0328 (13)0.0271 (13)0.0017 (11)0.0017 (10)0.0003 (10)
C30.0426 (14)0.0335 (14)0.0362 (14)0.0038 (11)0.0063 (10)0.0046 (11)
C40.0331 (12)0.0296 (13)0.0335 (13)0.0002 (10)0.0004 (9)0.0001 (10)
C50.0376 (13)0.0376 (14)0.0391 (14)0.0015 (11)0.0060 (10)0.0084 (11)
C60.0361 (13)0.0380 (15)0.0495 (16)0.0062 (11)0.0079 (11)0.0046 (12)
C70.0352 (12)0.0307 (14)0.0390 (14)0.0014 (9)0.0058 (10)0.0029 (10)
C80.0333 (14)0.0453 (17)0.075 (2)0.0061 (14)0.0015 (14)0.0054 (17)
C90.0514 (18)0.0419 (17)0.0512 (18)0.0119 (14)0.0163 (14)0.0066 (14)
C100.0349 (12)0.0262 (12)0.0337 (13)0.0054 (10)0.0036 (10)0.0009 (10)
C110.0316 (12)0.0353 (14)0.0297 (13)0.0039 (10)0.0025 (9)0.0027 (10)
C120.0405 (13)0.0354 (14)0.0347 (14)0.0013 (10)0.0047 (10)0.0077 (10)
C130.0377 (12)0.0306 (13)0.0364 (15)0.0061 (10)0.0006 (10)0.0046 (11)
C140.0354 (12)0.0311 (13)0.0313 (13)0.0046 (10)0.0025 (9)0.0015 (10)
C150.0364 (13)0.0289 (13)0.0350 (13)0.0008 (9)0.0055 (10)0.0025 (10)
C160.0462 (14)0.0404 (15)0.0289 (13)0.0047 (11)0.0048 (10)0.0010 (10)
C170.089 (3)0.0381 (17)0.0461 (19)0.0001 (17)0.0117 (17)0.0037 (14)
C180.058 (2)0.086 (3)0.041 (2)0.0192 (19)0.0080 (15)0.0067 (17)
C190.0414 (13)0.0396 (14)0.0265 (12)0.0028 (11)0.0012 (10)0.0007 (10)
C200.0431 (14)0.0429 (16)0.0484 (16)0.0109 (12)0.0076 (12)0.0067 (12)
C210.0393 (14)0.0483 (17)0.0543 (17)0.0098 (12)0.0161 (12)0.0097 (13)
C220.0462 (14)0.0384 (15)0.0307 (13)0.0002 (11)0.0010 (10)0.0050 (11)
C230.0616 (18)0.0461 (17)0.063 (2)0.0259 (14)0.0187 (15)0.0146 (14)
C240.0597 (17)0.0546 (18)0.0556 (18)0.0137 (14)0.0270 (14)0.0161 (14)
Geometric parameters (Å, º) top
O1—C11.387 (3)C11—C121.374 (3)
O1—H10.92 (3)C12—C131.384 (3)
O11—C111.397 (3)C12—H120.9300
O11—H110.87 (4)C13—C141.393 (3)
O22—C221.386 (3)C13—H130.9300
O22—H220.89 (4)C14—C151.393 (3)
C1—C61.374 (4)C14—C161.536 (3)
C1—C21.376 (3)C15—H150.9300
C2—C31.385 (3)C16—C171.534 (4)
C2—H20.9300C16—C191.540 (3)
C3—C41.381 (3)C16—C181.541 (4)
C3—H30.9300C17—H17A0.99 (3)
C4—C51.392 (3)C17—H17B0.95 (3)
C4—C71.537 (3)C17—H17C0.94 (4)
C5—C61.385 (3)C18—H18A0.98 (4)
C5—H50.9300C18—H18B1.01 (4)
C6—H60.9300C18—H18C0.96 (4)
C7—C81.532 (4)C19—C241.377 (4)
C7—C101.537 (3)C19—C201.383 (3)
C7—C91.545 (4)C20—C211.379 (4)
C8—H8A1.03 (3)C20—H200.9300
C8—H8B0.96 (4)C21—C221.370 (4)
C8—H8C0.96 (3)C21—H210.9300
C9—H9A1.00 (3)C22—C231.377 (4)
C9—H9B1.00 (3)C23—C241.378 (4)
C9—H9C1.03 (4)C23—H230.9300
C10—C111.398 (3)C24—H240.9300
C10—C151.399 (3)
C1—O1—H1113.7 (17)C13—C12—H12119.6
C11—O11—H11111 (3)C12—C13—C14120.5 (2)
C22—O22—H22106 (2)C12—C13—H13119.8
C6—C1—C2119.9 (2)C14—C13—H13119.8
C6—C1—O1122.8 (2)C15—C14—C13117.3 (2)
C2—C1—O1117.4 (2)C15—C14—C16122.8 (2)
C1—C2—C3120.2 (2)C13—C14—C16119.9 (2)
C1—C2—H2119.9C14—C15—C10123.9 (2)
C3—C2—H2119.9C14—C15—H15118.1
C4—C3—C2121.6 (2)C10—C15—H15118.1
C4—C3—H3119.2C17—C16—C14107.8 (2)
C2—C3—H3119.2C17—C16—C19111.0 (2)
C3—C4—C5116.8 (2)C14—C16—C19110.8 (2)
C3—C4—C7123.3 (2)C17—C16—C18108.1 (3)
C5—C4—C7119.8 (2)C14—C16—C18109.5 (2)
C6—C5—C4122.4 (2)C19—C16—C18109.6 (2)
C6—C5—H5118.8C16—C17—H17A115.1 (17)
C4—C5—H5118.8C16—C17—H17B113.5 (19)
C1—C6—C5119.2 (2)H17A—C17—H17B106 (3)
C1—C6—H6120.4C16—C17—H17C106 (2)
C5—C6—H6120.4H17A—C17—H17C108 (3)
C8—C7—C10108.9 (2)H17B—C17—H17C108 (3)
C8—C7—C4112.7 (2)C16—C18—H18A112 (2)
C10—C7—C4109.96 (18)C16—C18—H18B113 (2)
C8—C7—C9106.9 (2)H18A—C18—H18B110 (3)
C10—C7—C9111.8 (2)C16—C18—H18C114 (2)
C4—C7—C9106.7 (2)H18A—C18—H18C106 (3)
C7—C8—H8A109.5 (17)H18B—C18—H18C102 (3)
C7—C8—H8B111 (2)C24—C19—C20115.6 (2)
H8A—C8—H8B110 (3)C24—C19—C16121.4 (2)
C7—C8—H8C111.2 (17)C20—C19—C16122.9 (2)
H8A—C8—H8C107 (2)C21—C20—C19122.9 (2)
H8B—C8—H8C108 (3)C21—C20—H20118.6
C7—C9—H9A106.0 (18)C19—C20—H20118.6
C7—C9—H9B105.3 (18)C22—C21—C20119.8 (2)
H9A—C9—H9B117 (3)C22—C21—H21120.1
C7—C9—H9C111 (2)C20—C21—H21120.1
H9A—C9—H9C108 (3)C21—C22—C23118.9 (2)
H9B—C9—H9C109 (3)C21—C22—O22118.4 (2)
C11—C10—C15116.1 (2)C23—C22—O22122.6 (2)
C11—C10—C7121.9 (2)C22—C23—C24120.0 (2)
C15—C10—C7122.0 (2)C22—C23—H23120.0
C12—C11—O11118.7 (2)C24—C23—H23120.0
C12—C11—C10121.5 (2)C19—C24—C23122.8 (2)
O11—C11—C10119.7 (2)C19—C24—H24118.6
C11—C12—C13120.7 (2)C23—C24—H24118.6
C11—C12—H12119.6
C6—C1—C2—C30.9 (3)C12—C13—C14—C151.0 (3)
O1—C1—C2—C3178.7 (2)C12—C13—C14—C16178.6 (2)
C1—C2—C3—C40.2 (3)C13—C14—C15—C101.6 (3)
C2—C3—C4—C51.2 (3)C16—C14—C15—C10179.1 (2)
C2—C3—C4—C7174.8 (2)C11—C10—C15—C140.2 (3)
C3—C4—C5—C61.2 (3)C7—C10—C15—C14179.8 (2)
C7—C4—C5—C6175.0 (2)C15—C14—C16—C17105.4 (3)
C2—C1—C6—C50.9 (4)C13—C14—C16—C1772.0 (3)
O1—C1—C6—C5178.6 (2)C15—C14—C16—C1916.2 (3)
C4—C5—C6—C10.1 (4)C13—C14—C16—C19166.3 (2)
C3—C4—C7—C87.7 (3)C15—C14—C16—C18137.2 (3)
C5—C4—C7—C8176.4 (2)C13—C14—C16—C1845.4 (3)
C3—C4—C7—C10129.4 (2)C17—C16—C19—C24164.9 (3)
C5—C4—C7—C1054.8 (3)C14—C16—C19—C2475.4 (3)
C3—C4—C7—C9109.3 (3)C18—C16—C19—C2445.5 (4)
C5—C4—C7—C966.6 (3)C17—C16—C19—C2018.2 (4)
C8—C7—C10—C1160.7 (3)C14—C16—C19—C20101.6 (3)
C4—C7—C10—C1163.2 (3)C18—C16—C19—C20137.5 (3)
C9—C7—C10—C11178.5 (2)C24—C19—C20—C211.3 (4)
C8—C7—C10—C15118.9 (3)C16—C19—C20—C21175.9 (3)
C4—C7—C10—C15117.2 (2)C19—C20—C21—C220.2 (5)
C9—C7—C10—C151.1 (3)C20—C21—C22—C231.6 (4)
C15—C10—C11—C121.8 (3)C20—C21—C22—O22179.6 (3)
C7—C10—C11—C12177.8 (2)C21—C22—C23—C241.5 (5)
C15—C10—C11—O11179.1 (2)O22—C22—C23—C24179.7 (3)
C7—C10—C11—O110.5 (3)C20—C19—C24—C231.3 (4)
O11—C11—C12—C13179.7 (2)C16—C19—C24—C23175.9 (3)
C10—C11—C12—C132.3 (3)C22—C23—C24—C190.0 (5)
C11—C12—C13—C140.8 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···O11i0.92 (3)1.91 (3)2.813 (3)166 (3)
O11—H11···O22ii0.87 (4)1.95 (4)2.813 (3)177 (4)
O22—H22···O1iii0.89 (4)1.88 (4)2.756 (3)167 (3)
C8—H8A···O111.03 (3)2.31 (3)2.987 (4)122 (2)
C12—H12···Cg1iv0.932.743.564 (3)148
Symmetry codes: (i) x+1/2, y1/2, z; (ii) x+1/2, y+1/2, z+1/2; (iii) x, y, z1/2; (iv) x+1/2, y+1/2, z.

Experimental details

Crystal data
Chemical formulaC24H26O3
Mr362.45
Crystal system, space groupMonoclinic, Cc
Temperature (K)290
a, b, c (Å)6.2143 (2), 15.3978 (5), 20.7130 (7)
β (°) 93.729 (3)
V3)1977.76 (11)
Z4
Radiation typeMo Kα
µ (mm1)0.08
Crystal size (mm)0.30 × 0.27 × 0.07
Data collection
DiffractometerOxford Diffraction Xcalibur3 CCD
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
7160, 2469, 1729
Rint0.027
(sin θ/λ)max1)0.671
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.033, 0.082, 1.08
No. of reflections2469
No. of parameters305
No. of restraints2
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.12, 0.11

Computer programs: CrysAlis CCD (Oxford Diffraction, 2004), CrysAlis RED (Oxford Diffraction, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek,2003) and DIAMOND (Brandenburg, 2006), publCIF (Westrip, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···O11i0.92 (3)1.91 (3)2.813 (3)166 (3)
O11—H11···O22ii0.87 (4)1.95 (4)2.813 (3)177 (4)
O22—H22···O1iii0.89 (4)1.88 (4)2.756 (3)167 (3)
C8—H8A···O111.03 (3)2.31 (3)2.987 (4)122 (2)
C12—H12···Cg1iv0.932.743.564 (3)148
Symmetry codes: (i) x+1/2, y1/2, z; (ii) x+1/2, y+1/2, z+1/2; (iii) x, y, z1/2; (iv) x+1/2, y+1/2, z.
 

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