Crystal structure of (2S/2R,3S/3R)-3-hydroxy-2-phenyl­chroman-4-one

In the title mol­ecule, C₁₅H₁₂O₃, the C atoms bearing the hy­droxy group and the phenyl ring are disordered over two sets of sites with refined occupancies of 0.573 (7) and 0.427 (7). There is also disorder of the phenyl ring but the hy­droxy group was refined as ordered. The dihedral angles between the benzene ring of the chromane ring system and the phenyl ring are 89.7 (2)° for the major component of disorder and 72.1 (3)° for the minor component. Both disorder components of the the di­hydro­pyran ring are in a half-chair conformation. In the crystal, mol­ecules are linked by pairs of O—H...O hydrogen bonds, forming inversion dimers with an R₂²(10) graph-set motif. Weak C—H...π inter­actions link these dimers into ladders along [001].

Key indicators

• Single-crystal X-ray study
• T = 295 K
• Mean [sigma](C-C) = 0.004 Å
• Disorder in main residue
• R factor = 0.058
• wR factor = 0.148
• Data-to-parameter ratio = 10.9

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT241_ALERT_2_C High      Ueq as Compared to Neighbors for .....         O3 Check
PLAT340_ALERT_3_C Low Bond Precision on  C-C Bonds ...............     0.0043 Ang.
PLAT906_ALERT_3_C Large K value in the Analysis of Variance ......      3.979 Check
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L=  0.600          5 Report

Alert level G
PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite         10 Note
PLAT003_ALERT_2_G Number of Uiso or Uij Restrained non-H Atoms ...         12 Report
PLAT005_ALERT_5_G No _iucr_refine_instructions_details  in the CIF     Please Do !
PLAT176_ALERT_4_G The CIF-Embedded .res File Contains SADI Records          1 Report
PLAT300_ALERT_4_G Atom Site Occupancy of >C8     is Constrained at      0.573 Check
PLAT300_ALERT_4_G Atom Site Occupancy of >C9     is Constrained at      0.573 Check
PLAT300_ALERT_4_G Atom Site Occupancy of >C10    is Constrained at      0.573 Check
PLAT300_ALERT_4_G Atom Site Occupancy of >C11    is Constrained at      0.573 Check
PLAT300_ALERT_4_G Atom Site Occupancy of >C12    is Constrained at      0.573 Check
PLAT300_ALERT_4_G Atom Site Occupancy of >C13    is Constrained at      0.573 Check
PLAT300_ALERT_4_G Atom Site Occupancy of >C14    is Constrained at      0.573 Check
PLAT300_ALERT_4_G Atom Site Occupancy of >C15    is Constrained at      0.573 Check
PLAT300_ALERT_4_G Atom Site Occupancy of <C8A    is Constrained at      0.427 Check
PLAT300_ALERT_4_G Atom Site Occupancy of <C9A    is Constrained at      0.427 Check
PLAT300_ALERT_4_G Atom Site Occupancy of <C10A   is Constrained at      0.427 Check
PLAT300_ALERT_4_G Atom Site Occupancy of <C11A   is Constrained at      0.427 Check
PLAT300_ALERT_4_G Atom Site Occupancy of <C12A   is Constrained at      0.427 Check
PLAT300_ALERT_4_G Atom Site Occupancy of <C13A   is Constrained at      0.427 Check
PLAT300_ALERT_4_G Atom Site Occupancy of <C14A   is Constrained at      0.427 Check
PLAT300_ALERT_4_G Atom Site Occupancy of <C15A   is Constrained at      0.427 Check
PLAT301_ALERT_3_G Main Residue  Disorder ............ Percentage =         44 Note
PLAT720_ALERT_4_G Number of Unusual/Non-Standard Labels ..........          2 Note
PLAT779_ALERT_4_G Suspect or Irrelevant (Bond) Angle in CIF .... #          3 Check
              C9A  -O1   -C9      1.555   1.555   1.555             31.30 Deg.
PLAT779_ALERT_4_G Suspect or Irrelevant (Bond) Angle in CIF .... #          4 Check
              C8   -O3   -C8A     1.555   1.555   1.555             29.90 Deg.
PLAT779_ALERT_4_G Suspect or Irrelevant (Bond) Angle in CIF .... #         30 Check
              C8   -C7   -C8A     1.555   1.555   1.555             27.10 Deg.
PLAT793_ALERT_4_G The Model has Chirality at C8      (Centro SPGR)          R Verify
PLAT793_ALERT_4_G The Model has Chirality at C9      (Centro SPGR)          R Verify
PLAT793_ALERT_4_G The Model has Chirality at C8A     (Centro SPGR)          S Verify
PLAT793_ALERT_4_G The Model has Chirality at C9A     (Centro SPGR)          S Verify
PLAT811_ALERT_5_G No ADDSYM Analysis: Too Many Excluded Atoms ....          ! Info
PLAT860_ALERT_3_G Number of Least-Squares Restraints .............         30 Note
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Th(Min) ...          2 Report
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600          9 Note

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   4 ALERT level C = Check. Ensure it is not caused by an omission or oversight
  33 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
   6 ALERT type 3 Indicator that the structure quality may be low
  26 ALERT type 4 Improvement, methodology, query or suggestion
   2 ALERT type 5 Informative message, check

---

S1. Comment

Flavonoids are natural products derived from secondary metabolism of plants and play an important role in various biological processes (Harborne & Williams, 2000). All classes of flavonoids exhibit a variety of biological activities (Gaspar et al., 2014; Huang et al., 2007; Yu et al., 2003; Phosrithong et al., 2012). On the other hand, the Algar, Flynn and Oyamada (AFO) oxidation of substituted 2'-hydroxychalcones with alkaline hydrogen peroxide give flavonol derivatives (Juvale et al., 2013). Dihydroflavonol was also obtained by this reaction (Saxena et al., 1985; Tanaka & Sugino (2001). In this paper, we report the structure determination of the title compound resulting from the oxidation of 2'-hydroxychalcone using AFO reaction conditions.

The molecular structure of the title compound is shown in Fig. 1. The carbon atoms [C8 and C9] bearing the hydroxy group and the phenyl ring are disordered over two sets of sites with refined occupancies 0.573 (7) and 0.427 (7). This causes disorder of the phenyl ring [C10–C15] but the hydroxy group was refined as ordered. Atom O3 and the attached hydrogen atom occupy a single site. The dihedral angles between the benzene ring of the chromane ring system [C1–C6] and the phenyl ring are 89.7 (2)° for the major component of disorder [C10–C15] and 72.1 (3) for the minor component of disorder [C10A–C15A]. Both disorder components of the the dihydropyran are ring in a half-chair conformation. This type of geometry is comparable a published structure with a similar type of disorder (Piaskowska et al., 2013).

In the crystal, pairs of molecules are linked by O—H···O hydrogen bonds (Table 1), forming inversion dimers with R₂²(10) graph set motif. Weak C—H···pi interactions link these dimers into ladders along [001] (Fig. 2).

Related literature

For the synthesis and applications of flavone derivatives, see: Gaspar et al. (2014); Huang et al. (2007); Yu et al. (2003); Phosrithong et al. (2012); Harborne & Williams (2000); Tanaka & Sugino (2001); Saxena et al. (1985). For the synthesis of the title compound, see: Juvale et al. (2013). For a related structure, see: Piaskowska et al. (2013).

S2. Experimental

The title compound was obtained by subjecting the (E)-1-(2-hydroxyphenyl)-3-phenylprop-2-en-1-one to Algar-Flynn-Oymanda (AFO) conditions using aqueous hydrogen peroxide in the presence of sodium hydroxide. Colorless crystals of the title compound I with melting point: 449–251 K (yield: 52%) were grown by slow evaporation of a solution of the title compound in diethylether. The 1H NMR spectra is in full agreement with the proposed structure (Tanaka & Sugino, 2001). The relative position of the hydroxyl and phenyl ring on the new heterocyclic ring could not be determined efficiently by NMR spectroscopy (J H2—H3 ≈ 12.4 Hz). However, the X-ray structure determination revealed a trans-configuration.

S3. Refinement

Hydrogen atoms were located in differnce Fourier maps but introduced in calculated positions and treated as riding on their parent atom (C) with C—H = 0.93 and 0.98 Å and U_iso(H) = 1.2U_eq(C). The hydrogen atom of the hydroxy group was located in a difference map and refined isotropically with an O—H distance restraint of 0.85 (2) Å. The DELU and SADI commands in SHELXL (Sheldrick, 2008) were used in the refinment the disorder.

Computing details

Data collection: APEX2 (Bruker, 2011); cell refinement: SAINT (Bruker, 2011); data reduction: SAINT (Bruker, 2011); program(s) used to solve structure: SIR2002 (Burla et al., 2005); program(s) used to refine structure: SHELXL97 (Sheldrick, 2015); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: WinGX (Farrugia, 2012).

Figures

	Fig. 1. The molecule structure of the title compound. Displacement are drawn at the 30% probability level. H atoms are represented as small spheres of arbitrary radius. The minor component of disorder is not shown.
	Fig. 2. Part of the crystal structure of the title compound with hydrogen bonds shown as dashed lines and C—H···π intectations as green unbroken lines. The minor component of disorder is not shown.

3-Hydroxy-2-phenylchroman-4-one

Crystal data

C15H12O3	F(000) = 504
Mr = 240.25	Dx = 1.34 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1712 reflections
a = 5.3068 (3) Å	θ = 2.5–23.2°
b = 26.7110 (18) Å	µ = 0.09 mm^−1
c = 9.4679 (6) Å	T = 295 K
β = 117.431 (3)°	Prism, colorless
V = 1191.18 (13) Å^3	0.16 × 0.11 × 0.08 mm
Z = 4

Data collection

Bruker APEXII diffractometer	2356 independent reflections
Radiation source: Enraf Nonius FR590	1517 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.031
CCD rotation images, thick slices scans	θmax = 26.1°, θmin = 2.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 2002)	h = −5→6
Tmin = 0.615, Tmax = 0.745	k = −32→31
6701 measured reflections	l = −11→11

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.058	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.148	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ^2(Fo^2) + (0.0475P)^2 + 0.5327P] where P = (Fo^2 + 2Fc^2)/3
2356 reflections	(Δ/σ)max < 0.001
216 parameters	Δρmax = 0.14 e Å^−3
30 restraints	Δρmin = −0.16 e Å^−3

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	Occ. (<1)
O1	0.4498 (4)	0.85751 (6)	0.56442 (18)	0.0538 (5)
O2	0.8643 (5)	0.98972 (7)	0.6185 (2)	0.0768 (6)
O3	0.7507 (5)	0.93216 (8)	0.3576 (2)	0.0811 (7)
C1	0.5095 (5)	0.88656 (9)	0.6949 (3)	0.0487 (6)
C2	0.4263 (6)	0.86841 (11)	0.8046 (3)	0.0654 (8)
H2A	0.3327	0.8379	0.7875	0.079*
C3	0.4833 (7)	0.89589 (12)	0.9380 (3)	0.0782 (9)
H3A	0.428	0.8837	1.0116	0.094*
C4	0.6224 (8)	0.94163 (13)	0.9653 (3)	0.0826 (10)
H4A	0.6623	0.9598	1.057	0.099*
C5	0.7001 (7)	0.95974 (11)	0.8560 (3)	0.0694 (8)
H5A	0.7888	0.9908	0.8725	0.083*
C6	0.6481 (5)	0.93229 (9)	0.7201 (3)	0.0504 (6)
C7	0.7425 (6)	0.95026 (10)	0.6059 (3)	0.0590 (7)
C8	0.7356 (10)	0.91069 (15)	0.4871 (5)	0.0480 (15)	0.573 (7)
H8A	0.8973	0.888	0.5412	0.058*	0.573 (7)
C9	0.4642 (10)	0.88120 (18)	0.4324 (4)	0.0440 (14)	0.573 (7)
H9A	0.3063	0.905	0.386	0.053*	0.573 (7)
C8A	0.6023 (12)	0.9234 (2)	0.4446 (5)	0.048 (2)	0.427 (7)
H8AA	0.4052	0.9346	0.3836	0.058*	0.427 (7)
C9A	0.6092 (14)	0.8684 (2)	0.4818 (8)	0.0491 (18)	0.427 (7)
H9AA	0.8071	0.859	0.5506	0.059*	0.427 (7)
C10	0.4143 (17)	0.8417 (2)	0.3093 (6)	0.0438 (19)	0.573 (7)
C11	0.1560 (16)	0.8427 (3)	0.1717 (8)	0.066 (2)	0.573 (7)
H11A	0.0207	0.8667	0.1596	0.08*	0.573 (7)
C12	0.0997 (14)	0.8077 (3)	0.0521 (6)	0.082 (3)	0.573 (7)
H12A	−0.0731	0.8083	−0.0399	0.099*	0.573 (7)
C13	0.3018 (18)	0.7718 (3)	0.0702 (8)	0.075 (4)	0.573 (7)
H13A	0.2642	0.7484	−0.0098	0.09*	0.573 (7)
C14	0.5602 (16)	0.7708 (3)	0.2078 (9)	0.0589 (19)	0.573 (7)
H14A	0.6954	0.7468	0.2199	0.071*	0.573 (7)
C15	0.6165 (13)	0.8058 (3)	0.3273 (7)	0.0531 (19)	0.573 (7)
H15A	0.7893	0.8052	0.4194	0.064*	0.573 (7)
C10A	0.499 (2)	0.8360 (4)	0.3363 (9)	0.054 (3)	0.427 (7)
C11A	0.212 (2)	0.8324 (3)	0.2302 (10)	0.053 (2)	0.427 (7)
H11B	0.0805	0.8519	0.2447	0.063*	0.427 (7)
C12A	0.1204 (18)	0.7995 (4)	0.1023 (10)	0.063 (3)	0.427 (7)
H12B	−0.0718	0.797	0.0313	0.076*	0.427 (7)
C13A	0.317 (3)	0.7703 (3)	0.0806 (11)	0.063 (5)	0.427 (7)
H13B	0.2555	0.7482	−0.005	0.076*	0.427 (7)
C14A	0.604 (2)	0.7739 (5)	0.1867 (13)	0.081 (4)	0.427 (7)
H14B	0.735	0.7544	0.1721	0.097*	0.427 (7)
C15A	0.6950 (16)	0.8068 (5)	0.3145 (11)	0.066 (3)	0.427 (7)
H15B	0.8872	0.8093	0.3855	0.079*	0.427 (7)
H3O	0.843 (9)	0.9610 (11)	0.382 (5)	0.160 (18)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0702 (11)	0.0484 (10)	0.0507 (10)	−0.0118 (8)	0.0346 (9)	−0.0009 (7)
O2	0.0990 (16)	0.0637 (12)	0.0829 (14)	−0.0364 (11)	0.0548 (13)	−0.0229 (10)
O3	0.1237 (19)	0.0708 (14)	0.0775 (13)	−0.0378 (13)	0.0709 (14)	−0.0188 (11)
C1	0.0544 (14)	0.0501 (14)	0.0424 (12)	0.0046 (12)	0.0229 (11)	0.0071 (11)
C2	0.085 (2)	0.0643 (17)	0.0572 (16)	0.0026 (15)	0.0411 (16)	0.0131 (13)
C3	0.110 (3)	0.082 (2)	0.0583 (18)	0.0144 (19)	0.0524 (18)	0.0184 (16)
C4	0.124 (3)	0.080 (2)	0.0492 (16)	0.016 (2)	0.0449 (19)	0.0012 (15)
C5	0.092 (2)	0.0647 (18)	0.0500 (15)	−0.0016 (15)	0.0312 (15)	−0.0051 (13)
C6	0.0578 (15)	0.0511 (15)	0.0414 (12)	0.0033 (12)	0.0220 (12)	0.0015 (11)
C7	0.0714 (17)	0.0544 (16)	0.0567 (16)	−0.0152 (14)	0.0340 (14)	−0.0079 (12)
C8	0.046 (3)	0.052 (3)	0.049 (3)	−0.006 (2)	0.024 (2)	0.003 (2)
C9	0.049 (3)	0.045 (3)	0.046 (3)	−0.008 (2)	0.029 (2)	−0.003 (2)
C8A	0.067 (5)	0.040 (4)	0.044 (4)	0.003 (3)	0.030 (4)	0.005 (3)
C9A	0.040 (4)	0.053 (4)	0.053 (4)	−0.001 (3)	0.021 (3)	−0.001 (3)
C10	0.046 (5)	0.046 (4)	0.053 (4)	−0.013 (3)	0.034 (4)	−0.005 (3)
C11	0.050 (3)	0.058 (5)	0.073 (5)	0.002 (3)	0.013 (4)	−0.007 (4)
C12	0.067 (5)	0.085 (6)	0.075 (5)	0.000 (4)	0.016 (4)	−0.021 (4)
C13	0.062 (6)	0.088 (9)	0.080 (8)	−0.031 (5)	0.038 (6)	−0.027 (6)
C14	0.068 (4)	0.044 (4)	0.073 (4)	0.017 (3)	0.040 (4)	0.002 (3)
C15	0.051 (4)	0.061 (4)	0.044 (3)	0.001 (4)	0.018 (3)	0.000 (3)
C10A	0.053 (7)	0.051 (6)	0.061 (5)	−0.012 (4)	0.029 (4)	−0.005 (4)
C11A	0.052 (6)	0.045 (5)	0.067 (7)	0.014 (4)	0.032 (6)	0.002 (4)
C12A	0.052 (5)	0.063 (5)	0.058 (5)	−0.013 (4)	0.011 (4)	−0.014 (5)
C13A	0.101 (11)	0.022 (6)	0.064 (9)	0.011 (6)	0.036 (8)	−0.008 (5)
C14A	0.090 (7)	0.078 (8)	0.084 (8)	−0.001 (6)	0.050 (6)	−0.012 (6)
C15A	0.059 (5)	0.078 (6)	0.076 (5)	−0.002 (5)	0.045 (5)	−0.004 (4)

Geometric parameters (Å, º)

O1—C1	1.367 (3)	C8A—H8AA	0.98
O1—C9A	1.422 (4)	C9A—C10A	1.498 (4)
O1—C9	1.434 (4)	C9A—H9AA	0.98
O2—C7	1.213 (3)	C10—C11	1.39
O3—C8	1.389 (4)	C10—C15	1.39
O3—C8A	1.396 (4)	C11—C12	1.39
O3—H3O	0.885 (19)	C11—H11A	0.93
C1—C6	1.388 (3)	C12—C13	1.39
C1—C2	1.390 (3)	C12—H12A	0.93
C2—C3	1.369 (4)	C13—C14	1.39
C2—H2A	0.93	C13—H13A	0.93
C3—C4	1.389 (4)	C14—C15	1.39
C3—H3A	0.93	C14—H14A	0.93
C4—C5	1.367 (4)	C15—H15A	0.93
C4—H4A	0.93	C10A—C11A	1.39
C5—C6	1.394 (3)	C10A—C15A	1.39
C5—H5A	0.93	C11A—C12A	1.39
C6—C7	1.466 (3)	C11A—H11B	0.93
C7—C8	1.532 (4)	C12A—C13A	1.39
C7—C8A	1.534 (5)	C12A—H12B	0.93
C8—C9	1.509 (4)	C13A—C14A	1.39
C8—H8A	0.98	C13A—H13B	0.93
C9—C10	1.502 (4)	C14A—C15A	1.39
C9—H9A	0.98	C14A—H14B	0.93
C8A—C9A	1.507 (5)	C15A—H15B	0.93
C1—O1—C9A	115.6 (3)	O3—C8A—H8AA	109.9
C1—O1—C9	117.0 (2)	C9A—C8A—H8AA	109.9
C9A—O1—C9	31.3 (2)	C7—C8A—H8AA	109.9
C8—O3—C8A	29.9 (3)	O1—C9A—C10A	107.9 (5)
C8—O3—H3O	113 (3)	O1—C9A—C8A	111.8 (4)
C8A—O3—H3O	113 (3)	C10A—C9A—C8A	113.0 (6)
O1—C1—C6	122.6 (2)	O1—C9A—H9AA	108
O1—C1—C2	117.1 (2)	C10A—C9A—H9AA	108
C6—C1—C2	120.3 (2)	C8A—C9A—H9AA	108
C3—C2—C1	119.4 (3)	C11—C10—C15	120
C3—C2—H2A	120.3	C11—C10—C9	117.4 (5)
C1—C2—H2A	120.3	C15—C10—C9	122.6 (5)
C2—C3—C4	121.0 (3)	C12—C11—C10	120
C2—C3—H3A	119.5	C12—C11—H11A	120
C4—C3—H3A	119.5	C10—C11—H11A	120
C5—C4—C3	119.4 (3)	C11—C12—C13	120
C5—C4—H4A	120.3	C11—C12—H12A	120
C3—C4—H4A	120.3	C13—C12—H12A	120
C4—C5—C6	120.8 (3)	C14—C13—C12	120
C4—C5—H5A	119.6	C14—C13—H13A	120
C6—C5—H5A	119.6	C12—C13—H13A	120
C1—C6—C5	119.0 (2)	C13—C14—C15	120
C1—C6—C7	119.7 (2)	C13—C14—H14A	120
C5—C6—C7	121.3 (2)	C15—C14—H14A	120
O2—C7—C6	124.0 (2)	C14—C15—C10	120
O2—C7—C8	120.2 (2)	C14—C15—H15A	120
C6—C7—C8	114.5 (2)	C10—C15—H15A	120
O2—C7—C8A	119.7 (3)	C11A—C10A—C15A	120
C6—C7—C8A	114.0 (3)	C11A—C10A—C9A	122.6 (8)
C8—C7—C8A	27.1 (2)	C15A—C10A—C9A	117.3 (8)
O3—C8—C9	110.3 (3)	C12A—C11A—C10A	120
O3—C8—C7	111.8 (3)	C12A—C11A—H11B	120
C9—C8—C7	107.9 (3)	C10A—C11A—H11B	120
O3—C8—H8A	108.9	C11A—C12A—C13A	120
C9—C8—H8A	108.9	C11A—C12A—H12B	120
C7—C8—H8A	108.9	C13A—C12A—H12B	120
O1—C9—C10	107.8 (4)	C12A—C13A—C14A	120
O1—C9—C8	110.9 (3)	C12A—C13A—H13B	120
C10—C9—C8	115.6 (5)	C14A—C13A—H13B	120
O1—C9—H9A	107.4	C15A—C14A—C13A	120
C10—C9—H9A	107.4	C15A—C14A—H14B	120
C8—C9—H9A	107.4	C13A—C14A—H14B	120
O3—C8A—C9A	109.9 (4)	C14A—C15A—C10A	120
O3—C8A—C7	111.2 (3)	C14A—C15A—H15B	120
C9A—C8A—C7	105.9 (4)	C10A—C15A—H15B	120
C9A—O1—C1—C6	18.5 (4)	O2—C7—C8A—O3	32.0 (6)
C9—O1—C1—C6	−16.6 (4)	C6—C7—C8A—O3	−164.2 (3)
C9A—O1—C1—C2	−161.2 (4)	C8—C7—C8A—O3	−67.0 (5)
C9—O1—C1—C2	163.7 (3)	O2—C7—C8A—C9A	151.4 (4)
O1—C1—C2—C3	179.4 (2)	C6—C7—C8A—C9A	−44.8 (5)
C6—C1—C2—C3	−0.3 (4)	C8—C7—C8A—C9A	52.5 (5)
C1—C2—C3—C4	0.1 (5)	C1—O1—C9A—C10A	−175.4 (5)
C2—C3—C4—C5	0.9 (5)	C9—O1—C9A—C10A	−75.0 (9)
C3—C4—C5—C6	−1.7 (5)	C1—O1—C9A—C8A	−50.5 (6)
O1—C1—C6—C5	179.8 (2)	C9—O1—C9A—C8A	49.9 (5)
C2—C1—C6—C5	−0.5 (4)	O3—C8A—C9A—O1	−177.4 (4)
O1—C1—C6—C7	−1.6 (4)	C7—C8A—C9A—O1	62.3 (6)
C2—C1—C6—C7	178.1 (2)	O3—C8A—C9A—C10A	−55.4 (7)
C4—C5—C6—C1	1.5 (4)	C7—C8A—C9A—C10A	−175.7 (5)
C4—C5—C6—C7	−177.1 (3)	O1—C9—C10—C11	107.8 (5)
C1—C6—C7—O2	179.8 (3)	C8—C9—C10—C11	−127.5 (4)
C5—C6—C7—O2	−1.6 (4)	O1—C9—C10—C15	−73.4 (6)
C1—C6—C7—C8	−13.0 (4)	C8—C9—C10—C15	51.3 (6)
C5—C6—C7—C8	165.6 (3)	C15—C10—C11—C12	0
C1—C6—C7—C8A	16.8 (4)	C9—C10—C11—C12	178.8 (6)
C5—C6—C7—C8A	−164.6 (3)	C10—C11—C12—C13	0
C8A—O3—C8—C9	51.2 (5)	C11—C12—C13—C14	0
C8A—O3—C8—C7	−68.9 (4)	C12—C13—C14—C15	0
O2—C7—C8—O3	−28.7 (5)	C13—C14—C15—C10	0
C6—C7—C8—O3	163.6 (3)	C11—C10—C15—C14	0
C8A—C7—C8—O3	68.3 (4)	C9—C10—C15—C14	−178.7 (6)
O2—C7—C8—C9	−150.2 (3)	O1—C9A—C10A—C11A	50.0 (9)
C6—C7—C8—C9	42.1 (4)	C8A—C9A—C10A—C11A	−74.2 (8)
C8A—C7—C8—C9	−53.2 (5)	O1—C9A—C10A—C15A	−126.3 (6)
C1—O1—C9—C10	175.6 (4)	C8A—C9A—C10A—C15A	109.5 (6)
C9A—O1—C9—C10	80.1 (8)	C15A—C10A—C11A—C12A	0
C1—O1—C9—C8	48.1 (5)	C9A—C10A—C11A—C12A	−176.2 (9)
C9A—O1—C9—C8	−47.4 (5)	C10A—C11A—C12A—C13A	0
O3—C8—C9—O1	178.2 (3)	C11A—C12A—C13A—C14A	0
C7—C8—C9—O1	−59.4 (5)	C12A—C13A—C14A—C15A	0
O3—C8—C9—C10	55.1 (5)	C13A—C14A—C15A—C10A	0
C7—C8—C9—C10	177.6 (4)	C11A—C10A—C15A—C14A	0
C8—O3—C8A—C9A	−48.9 (5)	C9A—C10A—C15A—C14A	176.4 (9)
C8—O3—C8A—C7	68.1 (5)

Hydrogen-bond geometry (Å, º)

Cg1 and Cg2 are the centroids of the C10–C15 and C10A–C15A rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3O···O2^i	0.89 (4)	2.04 (4)	2.856 (3)	153 (4)
C3—H3A···Cg1^ii	0.93	2.74	3.596 (5)	153
C3—H3A···Cg2^ii	0.93	2.92	3.756 (5)	151

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