3-(Biphenyl-1-yl)-1-(4-tert-butyl­phen­yl)-3-hydroxy­prop-2-en-1-one

Zheng, C.-Y.; Zheng, J.; Wang, D.-J.

doi:10.1107/S1600536807031133

3-(Biphenyl-1-yl)-1-(4-tert-butylphenyl)-3-hydroxyprop-2-en-1-one

In the title compound, C₂₅H₂₄O₂, the molecular structure exists in a cis-enol form which is stabilized by an intramolecular O—H

O hydrogen bond. This hydrogen bond is described as an approximately symmetrical hydrogen bond. The three methyl groups are disordered over two positions, with a site occupancy ratio of ca 4:1.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807031133/is2173sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807031133/is2173Isup2.hkl Contains datablock I

CCDC reference: 657866

checkCIF report

Key indicators

Single-crystal X-ray study
T = 292 K
Mean (C-C) = 0.003 Å
Disorder in main residue
R factor = 0.056
wR factor = 0.157
Data-to-parameter ratio = 13.7

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT242_ALERT_2_B Check Low       Ueq as Compared to Neighbors for         C4

Alert level C
PLAT154_ALERT_1_C The su's on the Cell Angles are Equal  (x 10000)        200 Deg.
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.72 Ratio
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.12 Ratio
PLAT301_ALERT_3_C Main Residue  Disorder .........................      10.00 Perc.
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........          9

Alert level G
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......         48

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

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 ALERT type 2 Indicator that the structure model may be wrong or deficient
   3 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Comment top

1,3-Diketones posses a broad spectrum of useful and sometimes unique chemical properties, which make them extremely attractive as intermediates (Hasegawa et al., 1997; Morris et al., 1996). They are also used widely in the chemistry of metallocomplexes (Gorczynski et al., 2005; Liang et al., 2003), and 1,3-diketones structure has received increasing attention for studying tautomerism (Vila et al., 1991; Bertolasi et al., 1991; Gilli et al., 2004). The crystal structure of the title compound, (I), is in the enol form stabilized by an intramolecular hydrogen bond (Fig. 1 and Table 1). The distances of O1—H1 and O2—H1 are 1.28 (4) and 1.21 (3) Å, respectively. The central benzene ring (C14—C19) makes the dihedral angles of 4.22 (10) and 37.82 (11)° with benzene (C5—C10) and phenyl (C20—C25) rings, respectively.

Related literature top

For related literature, see: Bertolasi et al. (1991); Gilli et al. (2004); Gorczynski et al. (2005); Hasegawa et al. (1997); Liang et al. (2003); Morris et al. (1996); Vila et al. (1991).

Experimental top

1-(4-Phenylphenyl)ethanone (7.84 g, 0.04 mol), methyl 4-tert-butylbenzoate (7.68 g, 0.04 mol), NaNH₂ (1.95 g, 0.05 mol) and dry diethylether (60 ml) were mixed and stirred 6 h at room temperature under nitrogen. The mixture was then acidified with dilute hydrochloric acid and stirred until all solids dissolved. The ether layer was separated, washed with a saturated NaHCO₃ solution and dried over anhydrous Na₂SO₄. The solvent was removed by evaporation. The residual solid was recrystallized from an ethanol solution to give the title compound, (I) (yield 6.91 g, 48.5%; m.p. 396 K). Single crystals suitable for X-ray diffraction were grown by slow evaporation of a CH₂Cl₂—EtOH (2:1) solution at room temperature. ¹H NMR (CDCl₃, 400 MHz): 1.38(s, 9H, C(CH₃)₃), 6.89(s, 1H, enol C—H), 7.40–7.50(m, 3H, Ar—H), 7.52(d, 2H, 8.4 Hz), 7.64–7.67(m, 2H), 7.72(d, 2H, 8.4 Hz, Ar—H), 7.95(d, 2H, 8.4 Hz), 8.06(d, 2H, 8.4 Hz), 16.95(br s, 1H, enol O—H). Analysis, calculated for C₂₅H₂₄O₂: C 84.24, H 6.79%; found: C 84.26, H 6.74%.

Structure description top

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2001); software used to prepare material for publication: SHELXTL.

Figures top

Fig. 1. The molecular structure of (I), showing the atom-labeling scheme. Displacement ellipsoids are drawn at the 50% probability level. Only one component of the disordered methyl groups is shown. The dashed line indicates an intramolecular hydrogen bond.

3-(Biphenyl-1-yl)-1-(4-tert-butylphenyl)-3-hydroxyprop-2-en-1-one top

Crystal data top

C₂₅H₂₄O₂	Z = 2
M_r = 356.44	F(000) = 380
Triclinic, P1	D_x = 1.186 Mg m⁻³
Hall symbol: -P 1	Melting point: 396 K
a = 6.5578 (6) Å	Mo Kα radiation, λ = 0.71073 Å
b = 11.3548 (13) Å	Cell parameters from 1576 reflections
c = 14.1560 (13) Å	θ = 2.2–24.1°
α = 99.040 (2)°	µ = 0.07 mm⁻¹
β = 90.873 (2)°	T = 292 K
γ = 106.053 (2)°	Block, colorless
V = 998.49 (17) Å³	0.20 × 0.10 × 0.10 mm

Data collection top

Bruker APEX CCD area-detector diffractometer	2189 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.039
Graphite monochromator	θ_max = 26.0°, θ_min = 1.9°
Detector resolution: 0 pixels mm^-1	h = −7→8
φ and ω scans	k = −13→13
6592 measured reflections	l = −13→17
3845 independent reflections

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.056	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.157	H atoms treated by a mixture of independent and constrained refinement
S = 0.94	w = 1/[σ²(F_o²) + (0.0781P)²] where P = (F_o² + 2F_c²)/3
3845 reflections	(Δ/σ)_max = 0.001
281 parameters	Δρ_max = 0.15 e Å⁻³
48 restraints	Δρ_min = −0.20 e Å⁻³

Crystal data top

C₂₅H₂₄O₂	γ = 106.053 (2)°
M_r = 356.44	V = 998.49 (17) Å³
Triclinic, P1	Z = 2
a = 6.5578 (6) Å	Mo Kα radiation
b = 11.3548 (13) Å	µ = 0.07 mm⁻¹
c = 14.1560 (13) Å	T = 292 K
α = 99.040 (2)°	0.20 × 0.10 × 0.10 mm
β = 90.873 (2)°

Data collection top

Bruker APEX CCD area-detector diffractometer	2189 reflections with I > 2σ(I)
6592 measured reflections	R_int = 0.039
3845 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.056	48 restraints
wR(F²) = 0.157	H atoms treated by a mixture of independent and constrained refinement
S = 0.94	Δρ_max = 0.15 e Å⁻³
3845 reflections	Δρ_min = −0.20 e Å⁻³
281 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

	x	y	z	U_iso*/U_eq	Occ. (<1)
C1	0.1848 (7)	1.1478 (4)	0.4765 (3)	0.132 (2)	0.795 (5)
H1A	0.0733	1.1238	0.5188	0.197*	0.795 (5)
H1B	0.2174	1.0750	0.4439	0.197*	0.795 (5)
H1C	0.1393	1.1902	0.4303	0.197*	0.795 (5)
C2	0.3222 (8)	1.3461 (4)	0.5847 (3)	0.126 (2)	0.795 (5)
H2A	0.2566	1.3792	0.5380	0.189*	0.795 (5)
H2B	0.4452	1.4088	0.6155	0.189*	0.795 (5)
H2C	0.2229	1.3206	0.6318	0.189*	0.795 (5)
C3	0.5520 (7)	1.2707 (6)	0.4652 (3)	0.150 (3)	0.795 (5)
H3A	0.4936	1.3017	0.4150	0.225*	0.795 (5)
H3B	0.5944	1.1987	0.4384	0.225*	0.795 (5)
H3C	0.6734	1.3338	0.4969	0.225*	0.795 (5)
C1'	0.1691 (13)	1.2492 (14)	0.5431 (11)	0.101 (5)	0.205 (5)
H1'1	0.1317	1.2811	0.4885	0.151*	0.205 (5)
H1'2	0.1632	1.3055	0.6006	0.151*	0.205 (5)
H1'3	0.0710	1.1694	0.5450	0.151*	0.205 (5)
C2'	0.547 (2)	1.3667 (9)	0.5480 (12)	0.121 (6)	0.205 (5)
H2'1	0.5053	1.4136	0.5043	0.181*	0.205 (5)
H2'2	0.6867	1.3591	0.5346	0.181*	0.205 (5)
H2'3	0.5496	1.4088	0.6126	0.181*	0.205 (5)
C3'	0.417 (3)	1.1610 (13)	0.4444 (7)	0.116 (6)	0.205 (5)
H3'1	0.3188	1.0796	0.4374	0.174*	0.205 (5)
H3'2	0.5601	1.1540	0.4446	0.174*	0.205 (5)
H3'3	0.3928	1.2006	0.3919	0.174*	0.205 (5)
C4	0.3878 (4)	1.2363 (2)	0.53598 (17)	0.0765 (7)
C5	0.4578 (4)	1.17304 (19)	0.61368 (15)	0.0641 (6)
C6	0.3148 (4)	1.0916 (2)	0.65980 (17)	0.0771 (7)
H6	0.1705	1.0735	0.6430	0.092*
C7	0.3788 (3)	1.0358 (2)	0.73024 (16)	0.0714 (6)
H7	0.2772	0.9821	0.7604	0.086*
C8	0.5911 (3)	1.05849 (18)	0.75651 (14)	0.0582 (5)
C9	0.7339 (4)	1.1413 (2)	0.71199 (17)	0.0757 (7)
H9	0.8782	1.1599	0.7289	0.091*
C10	0.6680 (4)	1.1978 (2)	0.64268 (17)	0.0780 (7)
H10	0.7694	1.2545	0.6147	0.094*
C11	0.6698 (3)	0.99895 (19)	0.82931 (15)	0.0626 (6)
C12	0.5408 (3)	0.91601 (18)	0.88072 (14)	0.0600 (5)
H12	0.3940	0.8946	0.8695	0.072*
C13	0.6269 (3)	0.86427 (19)	0.94871 (15)	0.0617 (5)
C14	0.5022 (3)	0.77346 (18)	1.00488 (14)	0.0565 (5)
C15	0.2822 (3)	0.73328 (18)	0.99912 (15)	0.0611 (5)
H15	0.2061	0.7648	0.9584	0.073*
C16	0.1744 (3)	0.64730 (19)	1.05277 (15)	0.0619 (6)
H16	0.0265	0.6230	1.0485	0.074*
C17	0.2820 (3)	0.59616 (18)	1.11318 (14)	0.0555 (5)
C18	0.5022 (3)	0.6383 (2)	1.11969 (16)	0.0695 (6)
H18	0.5784	0.6070	1.1605	0.083*
C19	0.6108 (3)	0.7254 (2)	1.06730 (16)	0.0689 (6)
H19	0.7585	0.7524	1.0737	0.083*
C20	0.1692 (3)	0.50258 (18)	1.17043 (14)	0.0574 (5)
C21	−0.0199 (3)	0.5076 (2)	1.21068 (17)	0.0740 (6)
H21	−0.0777	0.5713	1.2015	0.089*
C22	−0.1241 (4)	0.4204 (2)	1.26393 (19)	0.0876 (8)
H22	−0.2509	0.4256	1.2903	0.105*
C23	−0.0412 (4)	0.3262 (2)	1.27805 (18)	0.0879 (8)
H23	−0.1102	0.2680	1.3150	0.105*
C24	0.1417 (4)	0.3177 (2)	1.23808 (18)	0.0884 (8)
H24	0.1961	0.2524	1.2466	0.106*
C25	0.2482 (4)	0.4050 (2)	1.18479 (16)	0.0747 (7)
H25	0.3742	0.3982	1.1583	0.090*
O1	0.8736 (2)	1.02827 (16)	0.84284 (13)	0.0910 (6)
O2	0.8298 (2)	0.89287 (17)	0.96452 (13)	0.0948 (6)
H1	0.887 (4)	0.966 (3)	0.909 (2)	0.142*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.161 (5)	0.128 (4)	0.103 (3)	0.020 (3)	−0.031 (3)	0.050 (3)
C2	0.187 (5)	0.108 (3)	0.113 (3)	0.083 (4)	0.009 (3)	0.031 (3)
C3	0.130 (4)	0.246 (7)	0.120 (4)	0.070 (4)	0.055 (3)	0.127 (5)
C1'	0.103 (8)	0.098 (9)	0.108 (9)	0.036 (7)	0.007 (7)	0.027 (7)
C2'	0.149 (10)	0.097 (8)	0.126 (10)	0.024 (7)	−0.007 (8)	0.063 (8)
C3'	0.153 (11)	0.133 (10)	0.080 (8)	0.056 (8)	−0.001 (7)	0.043 (7)
C4	0.1001 (18)	0.0725 (15)	0.0668 (16)	0.0307 (14)	0.0176 (13)	0.0285 (13)
C5	0.0808 (15)	0.0606 (13)	0.0561 (13)	0.0245 (11)	0.0183 (11)	0.0158 (11)
C6	0.0668 (14)	0.0888 (17)	0.0811 (17)	0.0176 (12)	0.0080 (12)	0.0382 (14)
C7	0.0631 (14)	0.0764 (15)	0.0761 (16)	0.0097 (11)	0.0108 (11)	0.0346 (13)
C8	0.0660 (13)	0.0561 (12)	0.0521 (13)	0.0149 (10)	0.0106 (10)	0.0111 (10)
C9	0.0665 (14)	0.0820 (16)	0.0796 (17)	0.0128 (12)	0.0138 (12)	0.0299 (14)
C10	0.0806 (17)	0.0782 (15)	0.0780 (17)	0.0142 (13)	0.0244 (13)	0.0345 (14)
C11	0.0619 (14)	0.0594 (13)	0.0622 (14)	0.0120 (11)	0.0009 (11)	0.0076 (11)
C12	0.0613 (12)	0.0597 (12)	0.0579 (13)	0.0128 (10)	0.0039 (10)	0.0142 (11)
C13	0.0595 (13)	0.0615 (13)	0.0588 (13)	0.0089 (10)	−0.0013 (10)	0.0100 (11)
C14	0.0636 (13)	0.0574 (12)	0.0495 (12)	0.0196 (10)	−0.0017 (10)	0.0081 (10)
C15	0.0610 (13)	0.0606 (13)	0.0637 (14)	0.0161 (10)	−0.0084 (10)	0.0197 (11)
C16	0.0541 (12)	0.0675 (13)	0.0671 (14)	0.0170 (10)	−0.0015 (10)	0.0206 (12)
C17	0.0619 (13)	0.0592 (12)	0.0491 (12)	0.0236 (10)	0.0003 (9)	0.0089 (10)
C18	0.0625 (14)	0.0919 (16)	0.0677 (14)	0.0329 (12)	0.0038 (11)	0.0337 (13)
C19	0.0579 (13)	0.0850 (15)	0.0700 (15)	0.0241 (11)	0.0029 (11)	0.0248 (13)
C20	0.0653 (13)	0.0621 (13)	0.0481 (12)	0.0229 (10)	0.0000 (10)	0.0106 (10)
C21	0.0718 (15)	0.0766 (15)	0.0821 (17)	0.0280 (12)	0.0105 (12)	0.0254 (13)
C22	0.0848 (17)	0.0919 (18)	0.0937 (19)	0.0264 (15)	0.0245 (14)	0.0341 (16)
C23	0.113 (2)	0.0825 (17)	0.0712 (17)	0.0225 (15)	0.0186 (15)	0.0314 (14)
C24	0.124 (2)	0.0828 (17)	0.0775 (18)	0.0476 (16)	0.0210 (16)	0.0357 (15)
C25	0.0949 (17)	0.0795 (15)	0.0662 (15)	0.0428 (13)	0.0163 (12)	0.0274 (13)
O1	0.0634 (11)	0.1048 (13)	0.1033 (13)	0.0045 (9)	−0.0041 (9)	0.0489 (11)
O2	0.0619 (10)	0.1084 (13)	0.1079 (14)	−0.0043 (9)	−0.0178 (9)	0.0530 (12)

Geometric parameters (Å, º) top

C1—C4	1.566 (4)	C9—C10	1.377 (3)
C1—H1A	0.9600	C9—H9	0.9300
C1—H1B	0.9600	C10—H10	0.9300
C1—H1C	0.9600	C11—O1	1.289 (2)
C2—C4	1.500 (4)	C11—C12	1.388 (3)
C2—H2A	0.9600	C12—C13	1.391 (3)
C2—H2B	0.9600	C12—H12	0.9300
C2—H2C	0.9600	C13—O2	1.287 (2)
C3—C4	1.496 (3)	C13—C14	1.475 (3)
C3—H3A	0.9600	C14—C15	1.384 (3)
C3—H3B	0.9600	C14—C19	1.390 (3)
C3—H3C	0.9600	C15—C16	1.378 (3)
C1'—C4	1.484 (6)	C15—H15	0.9300
C1'—H1'1	0.9600	C16—C17	1.389 (3)
C1'—H1'2	0.9600	C16—H16	0.9300
C1'—H1'3	0.9600	C17—C18	1.387 (3)
C2'—C4	1.541 (7)	C17—C20	1.479 (3)
C2'—H2'1	0.9600	C18—C19	1.375 (3)
C2'—H2'2	0.9600	C18—H18	0.9300
C2'—H2'3	0.9600	C19—H19	0.9300
C3'—C4	1.484 (7)	C20—C21	1.384 (3)
C3'—H3'1	0.9600	C20—C25	1.387 (3)
C3'—H3'2	0.9600	C21—C22	1.375 (3)
C3'—H3'3	0.9600	C21—H21	0.9300
C4—C5	1.534 (3)	C22—C23	1.365 (3)
C5—C10	1.371 (3)	C22—H22	0.9300
C5—C6	1.375 (3)	C23—C24	1.355 (3)
C6—C7	1.380 (3)	C23—H23	0.9300
C6—H6	0.9300	C24—C25	1.381 (3)
C7—C8	1.378 (3)	C24—H24	0.9300
C7—H7	0.9300	C25—H25	0.9300
C8—C9	1.370 (3)	O1—H1	1.28 (4)
C8—C11	1.477 (3)	O2—H1	1.21 (3)

C4—C1—H1A	109.5	C9—C8—C7	117.1 (2)
C4—C1—H1B	109.5	C9—C8—C11	119.3 (2)
C4—C1—H1C	109.5	C7—C8—C11	123.53 (18)
C4—C2—H2A	109.5	C8—C9—C10	121.4 (2)
C4—C2—H2B	109.5	C8—C9—H9	119.3
C4—C2—H2C	109.5	C10—C9—H9	119.3
C4—C3—H3A	109.5	C5—C10—C9	122.1 (2)
C4—C3—H3B	109.5	C5—C10—H10	119.0
C4—C3—H3C	109.5	C9—C10—H10	119.0
C4—C1'—H1'1	109.5	O1—C11—C12	120.27 (19)
C4—C1'—H1'2	109.5	O1—C11—C8	115.13 (19)
H1'1—C1'—H1'2	109.5	C12—C11—C8	124.6 (2)
C4—C1'—H1'3	109.5	C11—C12—C13	121.2 (2)
H1'1—C1'—H1'3	109.5	C11—C12—H12	119.4
H1'2—C1'—H1'3	109.5	C13—C12—H12	119.4
C4—C2'—H2'1	109.5	O2—C13—C12	119.88 (19)
C4—C2'—H2'2	109.5	O2—C13—C14	115.25 (19)
H2'1—C2'—H2'2	109.5	C12—C13—C14	124.85 (19)
C4—C2'—H2'3	109.5	C15—C14—C19	117.93 (19)
H2'1—C2'—H2'3	109.5	C15—C14—C13	123.62 (18)
H2'2—C2'—H2'3	109.5	C19—C14—C13	118.45 (19)
C4—C3'—H3'1	109.5	C16—C15—C14	121.01 (18)
C4—C3'—H3'2	109.5	C16—C15—H15	119.5
H3'1—C3'—H3'2	109.5	C14—C15—H15	119.5
C4—C3'—H3'3	109.5	C15—C16—C17	121.36 (18)
H3'1—C3'—H3'3	109.5	C15—C16—H16	119.3
H3'2—C3'—H3'3	109.5	C17—C16—H16	119.3
C3'—C4—C1'	113.2 (6)	C18—C17—C16	117.25 (18)
C3'—C4—C3	51.7 (6)	C18—C17—C20	120.55 (17)
C1'—C4—C3	131.9 (6)	C16—C17—C20	122.18 (18)
C3'—C4—C2	147.5 (6)	C19—C18—C17	121.67 (19)
C1'—C4—C2	52.3 (5)	C19—C18—H18	119.2
C3—C4—C2	112.4 (3)	C17—C18—H18	119.2
C3'—C4—C5	104.4 (6)	C18—C19—C14	120.7 (2)
C1'—C4—C5	114.6 (6)	C18—C19—H19	119.6
C3—C4—C5	113.5 (2)	C14—C19—H19	119.6
C2—C4—C5	108.1 (2)	C21—C20—C25	117.32 (19)
C3'—C4—C2'	109.7 (6)	C21—C20—C17	121.70 (18)
C1'—C4—C2'	109.1 (5)	C25—C20—C17	120.97 (18)
C3—C4—C2'	58.2 (6)	C22—C21—C20	121.5 (2)
C2—C4—C2'	60.9 (6)	C22—C21—H21	119.3
C5—C4—C2'	105.5 (5)	C20—C21—H21	119.3
C3'—C4—C1	62.0 (6)	C23—C22—C21	120.0 (2)
C1'—C4—C1	54.5 (6)	C23—C22—H22	120.0
C3—C4—C1	106.2 (3)	C21—C22—H22	120.0
C2—C4—C1	105.8 (3)	C24—C23—C22	119.8 (2)
C5—C4—C1	110.6 (2)	C24—C23—H23	120.1
C2'—C4—C1	143.9 (5)	C22—C23—H23	120.1
C10—C5—C6	116.3 (2)	C23—C24—C25	120.7 (2)
C10—C5—C4	121.3 (2)	C23—C24—H24	119.7
C6—C5—C4	122.3 (2)	C25—C24—H24	119.7
C5—C6—C7	122.0 (2)	C24—C25—C20	120.7 (2)
C5—C6—H6	119.0	C24—C25—H25	119.7
C7—C6—H6	119.0	C20—C25—H25	119.7
C8—C7—C6	121.00 (19)	C11—O1—H1	99.3 (13)
C8—C7—H7	119.5	C13—O2—H1	100.4 (14)
C6—C7—H7	119.5

C3'—C4—C5—C10	82.9 (7)	C11—C12—C13—O2	−0.3 (3)
C1'—C4—C5—C10	−152.7 (7)	C11—C12—C13—C14	−178.54 (17)
C3—C4—C5—C10	28.8 (4)	O2—C13—C14—C15	178.66 (19)
C2—C4—C5—C10	−96.6 (3)	C12—C13—C14—C15	−3.0 (3)
C2'—C4—C5—C10	−32.8 (7)	O2—C13—C14—C19	−1.2 (3)
C1—C4—C5—C10	148.0 (3)	C12—C13—C14—C19	177.1 (2)
C3'—C4—C5—C6	−98.9 (7)	C19—C14—C15—C16	−0.7 (3)
C1'—C4—C5—C6	25.5 (7)	C13—C14—C15—C16	179.40 (19)
C3—C4—C5—C6	−153.0 (3)	C14—C15—C16—C17	−1.2 (3)
C2—C4—C5—C6	81.6 (3)	C15—C16—C17—C18	2.1 (3)
C2'—C4—C5—C6	145.4 (7)	C15—C16—C17—C20	−179.21 (18)
C1—C4—C5—C6	−33.8 (3)	C16—C17—C18—C19	−1.3 (3)
C10—C5—C6—C7	−1.1 (3)	C20—C17—C18—C19	−179.93 (19)
C4—C5—C6—C7	−179.4 (2)	C17—C18—C19—C14	−0.6 (3)
C5—C6—C7—C8	−0.9 (4)	C15—C14—C19—C18	1.6 (3)
C6—C7—C8—C9	2.0 (3)	C13—C14—C19—C18	−178.52 (19)
C6—C7—C8—C11	−178.2 (2)	C18—C17—C20—C21	142.2 (2)
C7—C8—C9—C10	−1.1 (3)	C16—C17—C20—C21	−36.4 (3)
C11—C8—C9—C10	179.1 (2)	C18—C17—C20—C25	−38.7 (3)
C6—C5—C10—C9	2.0 (3)	C16—C17—C20—C25	142.7 (2)
C4—C5—C10—C9	−179.7 (2)	C25—C20—C21—C22	0.9 (3)
C8—C9—C10—C5	−0.9 (4)	C17—C20—C21—C22	−179.9 (2)
C9—C8—C11—O1	−2.2 (3)	C20—C21—C22—C23	0.0 (4)
C7—C8—C11—O1	178.0 (2)	C21—C22—C23—C24	−1.2 (4)
C9—C8—C11—C12	178.42 (19)	C22—C23—C24—C25	1.4 (4)
C7—C8—C11—C12	−1.4 (3)	C23—C24—C25—C20	−0.5 (4)
O1—C11—C12—C13	1.0 (3)	C21—C20—C25—C24	−0.6 (3)
C8—C11—C12—C13	−179.59 (19)	C17—C20—C25—C24	−179.8 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2	1.28 (3)	1.22 (3)	2.453 (3)	159 (3)
O1—H1···O2ⁱ	1.28 (4)	2.56 (3)	3.183 (2)	107.1 (17)

Symmetry code: (i) −x+2, −y+2, −z+2.

Experimental details

Crystal data
Chemical formula	C₂₅H₂₄O₂
M_r	356.44
Crystal system, space group	Triclinic, P1
Temperature (K)	292
a, b, c (Å)	6.5578 (6), 11.3548 (13), 14.1560 (13)
α, β, γ (°)	99.040 (2), 90.873 (2), 106.053 (2)
V (Å³)	998.49 (17)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.07
Crystal size (mm)	0.20 × 0.10 × 0.10

Data collection
Diffractometer	Bruker APEX CCD area-detector
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	6592, 3845, 2189
R_int	0.039
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.056, 0.157, 0.94
No. of reflections	3845
No. of parameters	281
No. of restraints	48
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.15, −0.20

Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1999), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 2001), SHELXTL.