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The title compound, C18H14O4, forms a supramolecular structure via [pi]-[pi] stacking and weak C-H...O and C-H...[pi] interactions. The benzo­pyran moiety is almost planar. The benzene ring of the phenyl­methyl acetate substituent is nearly perpendicular to the fused benzene and pyran rings and also to the methyl acetate group.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270104020712/sk1758sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270104020712/sk1758Isup2.hkl
Contains datablock I

CCDC reference: 254952

Comment top

Chromone and coumarin derivatives exhibit a wide spectrum of biological activity, including spasmolytic, antiarrhythmic, cardiothonic, antiviral, and anticancer and alkylating properties (Gabor, 1988; Valenti et al., 1993, 1998). In general, alkylating agents are the first class of cytostatics used for therapy (Zon, 1982). Under in vivo conditions, these agents alkylate nucleophilic centres of nucleobases and amino acids, resulting in either cleavage or cross-linking of double-stranded DNA molecules or proteins. Such cleavage causes damage of DNA, while covalent cross-links prevent unwinding of nucleic acids, which is functionally important in replication and transcription processes (Lindermann & Harbers, 1980).

In the multistep reaction of α-bromoketone, (I), with trimethyl phosphate, we obtained two products of the Perkov- and Arbuzov-type (Budzisz et al., 2002). This compound cyclizes to form a mixture of diastereoisomers which, subsequently, either lose dimethyl phosphate to give the Wittig-type (March, 1992) product, (III), or undergo 1,2-trans-elimination of water on the column to give the 3-phosphonic chromone derivative, (II). \sch

The alkylating properties of the test derivatives can be determined by an in vitro Preussmann test (Preussmann et al., 1969). This test permits the estimation of the direct ability of the compound to alkylate the model target molecule, 4-(4-nitrobenzyl)pyridine, and it provides a useful indication of alkylation potential for nucleophilic centres of aminoacids and nucleobases. However, due to its simplicity, the Preussmann test does not allow the determination of the mode of DNA alkylation. The title compound, (III), possesses very high (+++) alkylating activity (Budzisz et al., 2002). Against this background, and in order to obtain detailed information about the molecular structure of the title compund in the solid state, an X-ray structure investigation was carried out and the results are presented here.

Fig. 1 shows a perspective view of the molecule of (III) with the atom-numbering scheme. Most of the bond lengths and angles are comparable with expected values (Allen et al., 1987). The molecule of (III) consists of two condensed rings, a benzene and a pyran ring. The phenylmethylacetate group is attached in position 2. The two fused rings are almost coplanar; the dihedral angle between the best planes of rings A (C5—C10) and B (O1/C2—C4/C10/C9) is 3.61 (5)°. The best plane of ring B is nearly planar; the deviations of atoms O1, C2, C3, C4, C10 and C9 from the weighted least-squares plane are −0.023, 0.029, 0.017, −0.045, 0.030 and 0.014 Å, respectively, and this is typical for 255 structures with the benzopyran moiety found in the Cambridge Structural Database (CSD, Version 5.25, November, 2003; Allen, 2002). The planarity of the benzopyran moiety is confirmation of the aromatic character of this system. Neverthertheless, a lengthening of the C4—C10 and C4—C3 bonds is observed, to 1.469 (2) and 1.443 (2) Å, respectively, and the angle of the C3—C4—C10 valence bond decreases to 114.4 (1)°. In contrast, the shortest bond length and the largest angle are observed for atom C2, viz. 1.339 (2) Å and 123.6 (1)°, respectively. The C10—C9—C8 and C9—C10—C5 angles are 121.9 (1) and 118.0 (1)°, respectively. Similar variations in the geometric parameters of the pyran ring in the benzopyran system have been reported previously (Rybarczyk-Pirek & Nawrot-Modranka, 2004; Thinagar et al., 2003). It is worth mentioning that a search of the CSD for structures containing the benzopyran fragment, (IV), revealed similar geometric parameters for 255 fragments. Mean values for the geometric parameters of the above analyzed fragment are: C4—C10 1.45 (2), C4—C3 1.44 (2) and C2—C3 1.35 (2) Å, and C10—C4—C3 115 (2), C3—C2—O1 122 (2), C8—C9—C10 122 (2) and C5—C10—C9 117 (2)°.

Benzene ring C (C22—C27) of (III) is almost perpendicular to both the benzopyran moiety and the methylacetate group. The dihedral angle between ring C and rings A and B is 86.49 (2)°, and the O1—C2—C21—C22 and C3—C2—C21—C22 torsion angles are 63.5 (2) and −116.7 (2)°, respectively, showing a +synclinal (+sc) orientation of ring C with respect to the benzopyran system. The C22—C21—O28—C29 torsion angle of −76.2 (2)° confirms it is perpendicular to the methylacetate group. The structural parameters for the above-mentioned group are consistent with those of 14 similar structures found in the CSD that have a methylacetate group.

In compound (III), the supramolecular aggregation is stabilized by a combination of ππ stacking interactions and weak C—H···O and C—H···π interactions. Aromatic ππ stacking interactions are formed between rings A and B. The distances between the ring centroids, CgA···CgAv and CgB···CgBvi, are 3.682 (1) and 4.228 (1) Å, respectively [CgA is the centroid of ring A and CgB is the centroid of ring B; symmetry codes: (v) −x, −y, 1 − z; (vi) 1 − x, −y, 2 − z]. The perpendicular distances are 3.298 (1) and 3.290 (1) Å for rings A and B, respectively.

An analysis of the hydrogen bonding in (III) shows many non-conventional C—H···O and C—H···π interactions. Atom C7 is involved in a weak C—H···O intermolecular interaction with atom O4(x, y, z − 1), so generating a C(7) chain motif (Bernstein et al., 1995). Atom O4(-x, −y, 2 − z) is also an acceptor for a weak C4—H4···O4 interaction, which produces an R22(16) motif centred at (0, 0, 1). Atom C25 acts as a donor in an intermolecular interaction [graph set C(9)] with atom O29(x − 1, 1/2 − y, z − 1/2). Weak Csp3—H···πarene interactions, for instance C6—H6···CgCvii [CgC is the centroid of ring C; symmetry code: (vii) −x, −y, 1 − z Can this be replaced with (v), as the symmetry operator is the same for both?] complete the range of intermolecular interactions.

Experimental top

To acetate (I) (10 mmol) melted in a flask, trimethyl phosphite (12 mmol) was added dropwise at 383–388 K. After 30 min of heating, excess phosphite was removed by distillation, and the resulting yellow oil was applied on a silica gel column, which was then eluted with a mixture of chloroform-acetone (5:1, v/v). The product was purified by crystallization from acetone (yield 9%) Spectroscopic analysis: absorption (diethyl ether): Rf = 0.86; IR (KBr, ν, cm−1): 1764.1, 1658.8 (CO), 1620 (CC), 1034 (C—O—C); 1H NMR (CDCl3, δ, p.p.m.): 2.22 (s, 3H, CH3), 6.48 (s, 1H, CH), 6.62 (s, 1H, CH), 7.42–7.58 (m, 9H, aromatic); 13C NMR (75.5 MHz, CDCl3, δ, p.p.m.): 20.54 (–C—CH3), 74.43 (CH), 76.59 (CH), 123.98, 128.08, 131.16, 146.22, 170.39 (CO), 189.82 (CO); EIMS, m/z (%): 295 (100, M+ +1), 245 (16).

Refinement top

All H atoms were positioned geometrically and refined with a riding model; for phenyl H atoms, C—H = 0.93 Å and Uiso(H) = 1.2Ueq(C); for methyl H atoms, C—H = 0.96° and Uiso(H) = 1.5Ueq (C). The H atoms of the methyl group at C30 showed orientational disorder and were modelled with alternative positions occupied by 21 (1)%. Please clarify − 0.20 (2) in CIF table.

Computing details top

Data collection: WIN-EXPOSE in X-AREA (Stoe, 2000); cell refinement: WIN-CELL in X-AREA; data reduction: WIN-INTEGRATE in X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 1998); software used to prepare material for publication: PARST97 (Nardelli, 1996).

Figures top
[Figure 1] Fig. 1. A view of the molecule of (III), with the atom-labelling scheme. Displacement ellipsoids are drawn at the 50% probability level and H atoms are shown as msall spheres of arbitrary radii.
[Figure 2] Fig. 2. Part of the molecular packing of (III), showing the C—H···O and C—H···π interactions [symmetry codes: (i) x, y, z − 1; (ii) x − 1, 1/2 − y, z − 1/2; (iii) −x, −y, 2 − z; (iv) −x, −y, 1 − z. All H atoms, apart from H7, H25, H26 and H6, have been omitted for clarity.
[Figure 3] Fig. 3. A crystal packing diagram for (III), showing the intermolecular ππ stacking between benzopyran rings.
(±)-(4-Oxo-4H-chromen-2-yl)(phenyl)methyl acetate top
Crystal data top
C18H14O4F(000) = 616
Mr = 294.29Dx = 1.343 Mg m3
Monoclinic, P21/cMelting point = 304–305 K
Hall symbol: -P 2ybcMo Kα radiation, λ = 0.71073 Å
a = 6.8750 (6) ÅCell parameters from 15217 reflections
b = 25.3741 (17) Åθ = 1.6–26.2°
c = 8.3964 (8) ŵ = 0.10 mm1
β = 96.303 (8)°T = 193 K
V = 1455.9 (2) Å3Block, colourless
Z = 40.5 × 0.24 × 0.2 mm
Data collection top
Stoe IPDS II
diffractometer
2206 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.087
Graphite monochromatorθmax = 26.2°, θmin = 1.6°
Detector resolution: 150 pixels mm-1h = 88
ϕ scansk = 3031
15217 measured reflectionsl = 1010
2926 independent reflections
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)] = 0.042H-atom parameters constrained
wR(F2) = 0.118 w = 1/[σ2(Fo2) + (0.0763P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.00(Δ/σ)max < 0.001
2926 reflectionsΔρmax = 0.19 e Å3
202 parametersΔρmin = 0.18 e Å3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.059 (7)
Crystal data top
C18H14O4V = 1455.9 (2) Å3
Mr = 294.29Z = 4
Monoclinic, P21/cMo Kα radiation
a = 6.8750 (6) ŵ = 0.10 mm1
b = 25.3741 (17) ÅT = 193 K
c = 8.3964 (8) Å0.5 × 0.24 × 0.2 mm
β = 96.303 (8)°
Data collection top
Stoe IPDS II
diffractometer
2206 reflections with I > 2σ(I)
15217 measured reflectionsRint = 0.087
2926 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0420 restraints
wR(F2) = 0.118H-atom parameters constrained
S = 1.00Δρmax = 0.19 e Å3
2926 reflectionsΔρmin = 0.18 e Å3
202 parameters
Special details top

Experimental. The MS data were obtained on a Finnigan Matt mass spectrometer (100 eV ionization energy) with isobutane as reagent. UV/VIS spectra were obtained at 800–400 nm on a Lambda 19 Perkin-Elmer instrument. Satisfactory elemental analysis (± 0.4% of calculated values) were obtained using a Perkin Elmer PE 2400 CHNS analyser.

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*/UeqOcc. (<1)
O10.32755 (14)0.05141 (4)0.70955 (11)0.0409 (3)
O40.19011 (15)0.05977 (4)1.02986 (11)0.0468 (3)
O280.39522 (15)0.12629 (4)1.06871 (11)0.0434 (3)
O290.58368 (16)0.19774 (4)1.04834 (13)0.0544 (3)
C20.3266 (2)0.06268 (5)0.86765 (15)0.0382 (3)
C30.2782 (2)0.02777 (6)0.97622 (16)0.0402 (3)
C40.2212 (2)0.02541 (6)0.93165 (16)0.0401 (3)
C50.1308 (2)0.08337 (6)0.69206 (18)0.0466 (4)
C60.1177 (2)0.09178 (6)0.52962 (18)0.0492 (4)
C70.1818 (2)0.05319 (6)0.42925 (17)0.0480 (4)
C80.2535 (2)0.00584 (6)0.49045 (16)0.0444 (3)
C90.2612 (2)0.00269 (5)0.65502 (16)0.0398 (3)
C100.2041 (2)0.03573 (6)0.75852 (16)0.0406 (3)
C210.3880 (2)0.11900 (5)0.89722 (15)0.0402 (3)
C220.2443 (2)0.15729 (5)0.80935 (16)0.0384 (3)
C230.3011 (2)0.18872 (6)0.68748 (16)0.0423 (3)
C240.1694 (2)0.22378 (6)0.60799 (17)0.0457 (4)
C250.0182 (2)0.22833 (6)0.65152 (17)0.0452 (4)
C260.0755 (2)0.19683 (6)0.77386 (17)0.0438 (3)
C270.0545 (2)0.16113 (5)0.85138 (16)0.0412 (3)
C290.4964 (2)0.16907 (6)1.12943 (17)0.0452 (4)
C300.4775 (3)0.17515 (7)1.30329 (18)0.0551 (4)
H30.28140.03801.08280.048*
H50.09050.10960.75870.056*
H60.06610.12320.48660.059*
H70.17610.05950.31970.058*
H80.29590.01990.42340.053*
H270.01500.13970.93170.049*
H210.51860.12450.86350.048*
H230.42780.18630.65900.051*
H240.20730.24430.52500.055*
H250.10550.25230.59930.054*
H260.20140.19980.80360.053*
H30A0.38010.15121.33370.083*0.20 (2)
H30B0.43940.21071.32440.083*0.20 (2)
H30C0.60090.16761.36400.083*0.20 (2)
H30D0.56680.20181.34770.083*0.80 (2)
H30E0.50750.14231.35700.083*0.80 (2)
H30F0.34600.18541.31740.083*0.80 (2)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0480 (6)0.0426 (5)0.0325 (5)0.0022 (4)0.0062 (4)0.0004 (4)
O280.0524 (6)0.0438 (6)0.0334 (5)0.0029 (4)0.0019 (4)0.0010 (4)
C20.0389 (7)0.0437 (8)0.0318 (6)0.0024 (5)0.0030 (5)0.0014 (5)
O40.0553 (6)0.0458 (6)0.0394 (5)0.0059 (5)0.0058 (4)0.0050 (4)
C270.0462 (8)0.0424 (8)0.0354 (7)0.0046 (6)0.0064 (6)0.0020 (5)
C40.0385 (7)0.0435 (8)0.0386 (7)0.0017 (6)0.0053 (6)0.0019 (6)
C90.0397 (7)0.0418 (7)0.0379 (7)0.0027 (6)0.0040 (6)0.0022 (6)
C220.0437 (7)0.0375 (7)0.0339 (6)0.0020 (6)0.0032 (6)0.0031 (5)
C260.0418 (8)0.0477 (8)0.0420 (7)0.0008 (6)0.0052 (6)0.0060 (6)
C80.0456 (8)0.0528 (8)0.0351 (7)0.0034 (7)0.0056 (6)0.0003 (6)
C210.0448 (7)0.0437 (7)0.0320 (6)0.0008 (6)0.0043 (5)0.0007 (5)
C230.0429 (7)0.0448 (8)0.0398 (7)0.0005 (6)0.0068 (6)0.0011 (6)
O290.0542 (6)0.0560 (6)0.0532 (6)0.0111 (5)0.0074 (5)0.0080 (5)
C50.0512 (8)0.0434 (8)0.0443 (8)0.0015 (6)0.0017 (6)0.0001 (6)
C100.0404 (7)0.0440 (8)0.0372 (7)0.0033 (6)0.0027 (6)0.0003 (6)
C30.0443 (8)0.0437 (8)0.0325 (6)0.0007 (6)0.0034 (6)0.0000 (5)
C250.0473 (8)0.0427 (8)0.0446 (8)0.0031 (6)0.0002 (6)0.0028 (6)
C70.0490 (8)0.0561 (9)0.0383 (7)0.0083 (7)0.0025 (6)0.0066 (7)
C60.0546 (9)0.0457 (8)0.0460 (8)0.0015 (7)0.0014 (7)0.0077 (7)
C290.0454 (8)0.0454 (8)0.0437 (8)0.0019 (6)0.0009 (6)0.0042 (6)
C300.0674 (10)0.0560 (9)0.0404 (8)0.0033 (8)0.0001 (7)0.0067 (7)
C240.0540 (9)0.0423 (8)0.0413 (7)0.0009 (6)0.0072 (6)0.0052 (6)
Geometric parameters (Å, º) top
O1—C21.3586 (16)C23—C241.387 (2)
O1—C91.3784 (16)C23—H230.9300
O28—C291.3579 (18)O29—C291.2012 (19)
O28—C211.4472 (16)C5—C61.374 (2)
C2—C31.3391 (19)C5—C101.402 (2)
C2—C211.5030 (19)C5—H50.9300
O4—C41.2348 (17)C3—H30.9300
C27—C261.384 (2)C25—C241.383 (2)
C27—C221.392 (2)C25—H250.9300
C27—H270.9300C7—C61.395 (2)
C4—C31.443 (2)C7—H70.9300
C4—C101.4690 (19)C6—H60.9300
C9—C101.391 (2)C29—C301.488 (2)
C9—C81.3938 (19)C30—H30A0.9600
C22—C231.3869 (19)C30—H30B0.9600
C22—C211.5181 (19)C30—H30C0.9600
C26—C251.392 (2)C30—H30D0.9600
C26—H260.9300C30—H30E0.9600
C8—C71.376 (2)C30—H30F0.9600
C8—H80.9300C24—H240.9300
C21—H210.9800
C2—O1—C9118.46 (11)C2—C3—H3119.2
C29—O28—C21115.84 (11)C4—C3—H3119.2
C3—C2—O1123.64 (13)C24—C25—C26119.65 (13)
C3—C2—C21127.07 (12)C24—C25—H25120.2
O1—C2—C21109.28 (11)C26—C25—H25120.2
C26—C27—C22120.10 (13)C8—C7—C6120.74 (14)
C26—C27—H27120.0C8—C7—H7119.6
C22—C27—H27120.0C6—C7—H7119.6
O4—C4—C3123.30 (12)C5—C6—C7120.02 (14)
O4—C4—C10122.28 (13)C5—C6—H6120.0
C3—C4—C10114.41 (12)C7—C6—H6120.0
O1—C9—C10121.79 (12)O29—C29—O28122.58 (13)
O1—C9—C8116.33 (12)O29—C29—C30126.59 (14)
C10—C9—C8121.88 (13)O28—C29—C30110.81 (14)
C23—C22—C27119.64 (13)C29—C30—H30A109.5
C23—C22—C21120.38 (13)C29—C30—H30B109.5
C27—C22—C21119.98 (12)H30A—C30—H30B109.5
C27—C26—C25120.15 (13)C29—C30—H30C109.5
C27—C26—H26119.9H30A—C30—H30C109.5
C25—C26—H26119.9H30B—C30—H30C109.5
C7—C8—C9118.59 (14)C29—C30—H30D109.5
C7—C8—H8120.7H30A—C30—H30D141.1
C9—C8—H8120.7H30B—C30—H30D56.3
O28—C21—C2105.32 (11)H30C—C30—H30D56.3
O28—C21—C22110.55 (11)C29—C30—H30E109.5
C2—C21—C22111.85 (11)H30A—C30—H30E56.3
O28—C21—H21109.7H30B—C30—H30E141.1
C2—C21—H21109.7H30C—C30—H30E56.3
C22—C21—H21109.7H30D—C30—H30E109.5
C22—C23—C24120.12 (14)C29—C30—H30F109.5
C22—C23—H23119.9H30A—C30—H30F56.3
C24—C23—H23119.9H30B—C30—H30F56.3
C6—C5—C10120.71 (15)H30C—C30—H30F141.1
C6—C5—H5119.6H30D—C30—H30F109.5
C10—C5—H5119.6H30E—C30—H30F109.5
C9—C10—C5118.00 (13)C25—C24—C23120.32 (14)
C9—C10—C4119.74 (13)C25—C24—H24119.8
C5—C10—C4122.26 (13)C23—C24—H24119.8
C2—C3—C4121.52 (12)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C7—H7···O4i0.932.453.364 (1)169
C25—H25···O29ii0.932.483.353 (1)156
C27—H27···O4iii0.932.513.286 (1)141
C6—H6···CgCiv0.932.733.615 (1)160
Symmetry codes: (i) x, y, z1; (ii) x1, y+1/2, z1/2; (iii) x, y, z+2; (iv) x, y, z+1.

Experimental details

Crystal data
Chemical formulaC18H14O4
Mr294.29
Crystal system, space groupMonoclinic, P21/c
Temperature (K)193
a, b, c (Å)6.8750 (6), 25.3741 (17), 8.3964 (8)
β (°) 96.303 (8)
V3)1455.9 (2)
Z4
Radiation typeMo Kα
µ (mm1)0.10
Crystal size (mm)0.5 × 0.24 × 0.2
Data collection
DiffractometerStoe IPDS II
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
15217, 2926, 2206
Rint0.087
(sin θ/λ)max1)0.621
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.042, 0.118, 1.00
No. of reflections2926
No. of parameters202
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.19, 0.18

Computer programs: WIN-EXPOSE in X-AREA (Stoe, 2000), WIN-CELL in X-AREA, WIN-INTEGRATE in X-AREA, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), PLATON (Spek, 1998), PARST97 (Nardelli, 1996).

Selected geometric parameters (Å, º) top
O1—C21.3586 (16)C9—C81.3938 (19)
O1—C91.3784 (16)C22—C231.3869 (19)
O28—C291.3579 (18)C22—C211.5181 (19)
O28—C211.4472 (16)C26—C251.392 (2)
C2—C31.3391 (19)C8—C71.376 (2)
C2—C211.5030 (19)C23—C241.387 (2)
O4—C41.2348 (17)O29—C291.2012 (19)
C27—C261.384 (2)C5—C61.374 (2)
C27—C221.392 (2)C5—C101.402 (2)
C4—C31.443 (2)C25—C241.383 (2)
C4—C101.4690 (19)C7—C61.395 (2)
C9—C101.391 (2)C29—C301.488 (2)
C2—O1—C9118.46 (11)O1—C9—C8116.33 (12)
C29—O28—C21115.84 (11)O28—C21—C2105.32 (11)
C3—C2—O1123.64 (13)O28—C21—C22110.55 (11)
O1—C2—C21109.28 (11)O29—C29—O28122.58 (13)
O4—C4—C3123.30 (12)O29—C29—C30126.59 (14)
O4—C4—C10122.28 (13)O28—C29—C30110.81 (14)
O1—C9—C10121.79 (12)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C7—H7···O4i0.932.453.364 (1)169
C25—H25···O29ii0.932.483.353 (1)156
C27—H27···O4iii0.932.513.286 (1)141
C6—H6···CgCiv0.932.733.615 (1)160
Symmetry codes: (i) x, y, z1; (ii) x1, y+1/2, z1/2; (iii) x, y, z+2; (iv) x, y, z+1.
 

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