3-(1-Hydroxy-2-phenylprop-2-en-1-yl)-
phenol

Ignez Caracelli,a* Julio Zukerman-Schpector,b Fateh V.

Singh,c Hélio A. Stefanic and Edward R. T. Tiekinkd

aBioMat-Physics Department, Univ Estadual Paulista, UNESP, 17033-360 Bauru, SP,

Brazil, bDepartment of Chemistry, Universidade Federal de São Carlos, 13565-905

São Carlos, SP, Brazil, cDepartamento de Farmácia, Faculdade de Ciências

Farmacêuticas, Universidade de São Paulo, São Paulo-SP, Brazil, and dDepartment of

Chemistry, University of Malaya, Kuala Lumpur 50603, Malaysia

Correspondence e-mail: ignez@fc.unesp.br

Received 29 March 2010; accepted 30 March 2010

Key indicators: single-crystal X-ray study; T = 100 K; mean �(C–C) = 0.004 Å;

R factor = 0.035; wR factor = 0.084; data-to-parameter ratio = 7.6.

Two independent pseudo-enantiomeric molecules comprise

the asymmetric unit in the title compound, C15H14O2. While

the central O—C—C—C residue approaches planarity

[torsion angles = �15.8 (3) (molecule a) and 15.4 (3)�

(molecule b)], the benzene rings are approximately ortho-

gonal [the dihedral angles formed between the benzene rings

are 62.89 (12) (molecule a) and 80.15 (12)� (molecule b)].

Two-dimensional arrays in the ab plane sustained by O—

H� � �O hydrogen bonding are found in the crystal structure.

Related literature

For the synthesis of the title compound and the motivation for

its study, see: Singh et al. (2010).

Experimental

Crystal data

C15H14O2

Mr = 226.28
Orthorhombic, P212121

a = 9.1301 (2) Å

b = 10.2026 (2) Å
c = 24.8379 (6) Å
V = 2313.67 (9) Å3

Z = 8

Mo K� radiation
� = 0.09 mm�1

T = 100 K
0.27 � 0.13 � 0.13 mm

Data collection

Bruker SMART APEXII
diffractometer

Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
Tmin = 0.883, Tmax = 1

31791 measured reflections
2368 independent reflections
2150 reflections with I > 2�(I)
Rint = 0.042

Refinement

R[F 2 > 2�(F 2)] = 0.035
wR(F 2) = 0.084
S = 1.15
2368 reflections

311 parameters
H-atom parameters constrained
��max = 0.17 e �3

��min = �0.15 e �3

Table 1
Hydrogen-bond geometry (Å, �).

D—H� � �A D—H H� � �A D� � �A D—H� � �A

O1—H1O� � �O4 0.84 1.89 2.727 (2) 175
O2—H2O� � �O1i 0.84 2.00 2.823 (2) 168
O3—H3O� � �O2ii 0.84 1.89 2.728 (2) 174
O4—H4O� � �O3iii 0.84 2.02 2.825 (2) 161

Symmetry codes: (i) �xþ 2; yþ 1
2;�zþ 1

2; (ii) x; y� 1; z; (iii) �xþ 1; yþ 1
2;�zþ 1

2.

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT

(Bruker, 2007); data reduction: SAINT; program(s) used to solve

structure: SIR97 (Altomare et al., 1999); program(s) used to refine

structure: SHELXL97 (Sheldrick, 2008); molecular graphics:

ORTEP-3 (Farrugia, 1997), DIAMOND (Brandenburg, 2006) and

MarvinSketch (Chemaxon, 2009); software used to prepare material

for publication: publCIF (Westrip, 2010).

We thank FAPESP (07/59404–2 to HAS), CNPq (472237/

2008–0 to IC, 300613/2007 to HAS, and 306532/2009–3 to JZ-

S) and CAPES (808/2009 to JZ-S and IC) for financial support.

Supplementary data and figures for this paper are available from the
IUCr electronic archives (Reference: HG2665).

References

Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C.,
Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J.
Appl. Cryst. 32, 115–119.

Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany.
Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin,

USA.
Chemaxon (2009). MarvinSketch. URL: www.chemaxon.com.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.
Singh, F. V., Pena, J. M. & Stefani, H. A. (2010). Tetrahedron Lett. 51, 1671–

1673.
Westrip, S. P. (2010). publCIF. In preparation.

organic compounds

Acta Cryst. (2010). E66, o1033 doi:10.1107/S1600536810012018 Caracelli et al. o1033

Acta Crystallographica Section E

Structure Reports
Online

ISSN 1600-5368

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supplementary materials



supplementary materials

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Acta Cryst. (2010). E66, o1033    [ doi:10.1107/S1600536810012018 ]

3-(1-Hydroxy-2-phenylprop-2-en-1-yl)phenol

I. Caracelli, J. Zukerman-Schpector, F. V. Singh, H. A. Stefani and E. R. T. Tiekink

Comment

The title compound, (I), was prepared in connection with a study of the synthesis of α,β-epoxy ketones using a palladium-
catalyzed epoxidation-oxidation sequence (Singh et al., 2010). Two independent molecules, molecule a (Fig. 1) and mo-
lecule b (Fig. 2), comprise the crystallographic asymmetric unit. Molecules a and b are related by a non-crystallographic
centre of inversion. Close intramolecular O2···H9b and O4···H24b contacts which close S(6) motifs are noted, Table 1. These
interactions are probably responsible for the near planarity of the O2–C7–C8–C9 and O4–C22–C23–C24 residues as seen
in the respective torsion angles of -15.8 (3) and 15.4 (3)°. The benzene rings are approximately orthogonal [the dihedral
angles formed between the benzene rings is 62.89 (12) ° (molecule a) and 80.15 (12) ° (molecule b)].

In the crystal packing, O–H···O interactions predominate, Table 1, and lead to the formation of two-dimensional arrays
in the ab plane, Fig. 3, that stack along the c axis, Fig. 4.

Experimental

The synthesis was described in Singh et al. (2010) and crystals were grown by slow evaporation from a solution of 15%
of acetyl acetate in hexane.

Refinement

The H atoms were geometrically placed (O–H = 0.84 Å and C–H = 0.95–1.00 Å) and refined as riding with Uiso(H) =

1.2Ueq(C) and Uiso(H) = 1.5Ueq(O). In the absence of significant anomalous scattering effects, 1752 Friedel pairs were

averaged in the final refinement.

Figures

Fig. 1. The molecular structure of the first independent molecule in (I) showing atom la-
belling scheme and displacement ellipsoids at the 50% probability level (arbitrary spheres for
the H atoms).

Fig. 2. The molecular structure of the second independent molecule in (I) showing atom la-
belling scheme and displacement ellipsoids at the 50% probability level (arbitrary spheres for
the H atoms).

http://dx.doi.org/10.1107/S1600536810012018
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http://scripts.iucr.org/cgi-bin/citedin?search_on=name&author_name=Singh,%20F.V.
http://scripts.iucr.org/cgi-bin/citedin?search_on=name&author_name=Stefani,%20H.A.
http://scripts.iucr.org/cgi-bin/citedin?search_on=name&author_name=Tiekink,%20E.R.T.


supplementary materials

sup-2

Fig. 3. The supramolecular arrangement showing the formation of two-dimensional arrays in
the ab plane.

Fig. 4. The stacking of the two-dimensional arrays along the c axis.

3-(1-Hydroxy-2-phenylprop-2-en-1-yl)phenol

Crystal data

C15H14O2 F(000) = 960

Mr = 226.28 Dx = 1.299 Mg m−3

Orthorhombic, P212121 Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab Cell parameters from 9974 reflections
a = 9.1301 (2) Å θ = 2.5–25.0°
b = 10.2026 (2) Å µ = 0.09 mm−1

c = 24.8379 (6) Å T = 100 K

V = 2313.67 (9) Å3 Block, colourless
Z = 8 0.27 × 0.13 × 0.13 mm

Data collection

Bruker SMART APEXII
diffractometer 2368 independent reflections

Radiation source: sealed tube 2150 reflections with I > 2σ(I)
graphite Rint = 0.042

φ and ω scans θmax = 25.1°, θmin = 1.6°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996) h = −10→10

Tmin = 0.883, Tmax = 1 k = −12→11
31791 measured reflections l = −29→29

Refinement

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)] = 0.035
Hydrogen site location: inferred from neighbouring
sites



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sup-3

wR(F2) = 0.084 H-atom parameters constrained

S = 1.15
w = 1/[σ2(Fo

2) + (0.0381P)2 + 0.6989P]
where P = (Fo

2 + 2Fc
2)/3

2368 reflections (Δ/σ)max < 0.001

311 parameters Δρmax = 0.17 e Å−3

0 restraints Δρmin = −0.15 e Å−3

Special details

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The
cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between
s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is
used for estimating s.u.'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, convention-

al 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)

x y z Uiso*/Ueq

O1 1.06075 (18) 0.29142 (16) 0.21652 (7) 0.0217 (4)
H1O 0.9766 0.2581 0.2163 0.033*
O2 0.70773 (18) 0.69539 (17) 0.21929 (6) 0.0203 (4)
H2O 0.7719 0.7160 0.2420 0.031*
C1 1.0535 (3) 0.4174 (2) 0.19749 (8) 0.0177 (5)
C2 0.9221 (3) 0.4834 (3) 0.19232 (9) 0.0177 (5)
H2 0.8332 0.4418 0.2023 0.021*
C3 0.9201 (3) 0.6112 (2) 0.17244 (9) 0.0169 (5)
C4 1.0502 (3) 0.6719 (3) 0.15824 (9) 0.0189 (5)
H4 1.0492 0.7590 0.1447 0.023*
C5 1.1816 (3) 0.6054 (2) 0.16377 (9) 0.0194 (5)
H5 1.2708 0.6474 0.1541 0.023*
C6 1.1841 (3) 0.4781 (3) 0.18328 (9) 0.0194 (5)
H6 1.2744 0.4327 0.1869 0.023*
C7 0.7742 (2) 0.6817 (2) 0.16736 (9) 0.0176 (5)
H7 0.7917 0.7710 0.1520 0.021*
C8 0.6701 (3) 0.6085 (2) 0.13080 (9) 0.0177 (5)
C9 0.5564 (3) 0.5408 (2) 0.14915 (10) 0.0204 (5)
H9A 0.4929 0.4973 0.1247 0.025*
H9B 0.5384 0.5359 0.1868 0.025*
C10 0.7000 (3) 0.6172 (2) 0.07155 (9) 0.0182 (5)
C11 0.6005 (3) 0.6817 (3) 0.03877 (10) 0.0260 (6)
H11 0.5163 0.7213 0.0543 0.031*
C12 0.6225 (3) 0.6892 (3) −0.01631 (10) 0.0288 (6)
H12 0.5540 0.7345 −0.0383 0.035*



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sup-4

C13 0.7432 (3) 0.6313 (3) −0.03926 (10) 0.0270 (6)
H13 0.7582 0.6362 −0.0771 0.032*
C14 0.8429 (3) 0.5659 (3) −0.00699 (10) 0.0286 (6)
H14 0.9257 0.5247 −0.0228 0.034*
C15 0.8223 (3) 0.5602 (3) 0.04816 (10) 0.0242 (6)
H15 0.8925 0.5171 0.0701 0.029*
O3 0.43410 (18) −0.19891 (17) 0.22734 (7) 0.0221 (4)
H3O 0.5183 −0.2321 0.2274 0.033*
O4 0.78763 (17) 0.18479 (17) 0.20933 (6) 0.0200 (4)
H4O 0.7310 0.2091 0.2341 0.030*
C16 0.4372 (3) −0.0816 (2) 0.20043 (9) 0.0171 (5)
C17 0.5664 (3) −0.0131 (2) 0.19299 (9) 0.0186 (5)
H17 0.6560 −0.0481 0.2061 0.022*
C18 0.5656 (3) 0.1067 (2) 0.16646 (9) 0.0168 (5)
C19 0.4346 (3) 0.1569 (2) 0.14687 (9) 0.0205 (5)
H19 0.4335 0.2381 0.1282 0.025*
C20 0.3058 (3) 0.0881 (2) 0.15472 (9) 0.0208 (5)
H20 0.2162 0.1228 0.1415 0.025*
C21 0.3063 (3) −0.0308 (3) 0.18165 (9) 0.0188 (5)
H21 0.2173 −0.0772 0.1872 0.023*
C22 0.7091 (3) 0.1805 (2) 0.15946 (9) 0.0180 (5)
H22 0.6873 0.2722 0.1476 0.022*
C23 0.8034 (3) 0.1145 (2) 0.11719 (9) 0.0181 (5)
C24 0.9210 (3) 0.0451 (3) 0.13067 (10) 0.0237 (6)
H24A 0.9762 0.0015 0.1036 0.028*
H24B 0.9499 0.0391 0.1673 0.028*
C25 0.7532 (3) 0.1273 (2) 0.06044 (9) 0.0198 (5)
C26 0.6886 (3) 0.2420 (3) 0.04143 (10) 0.0291 (6)
H26 0.6748 0.3136 0.0653 0.035*
C27 0.6439 (3) 0.2536 (3) −0.01169 (11) 0.0367 (7)
H27 0.5991 0.3323 −0.0239 0.044*
C28 0.6648 (3) 0.1505 (3) −0.04687 (11) 0.0349 (7)
H28 0.6359 0.1585 −0.0835 0.042*
C29 0.7273 (3) 0.0368 (3) −0.02884 (10) 0.0325 (7)
H29 0.7414 −0.0342 −0.0530 0.039*
C30 0.7702 (3) 0.0245 (3) 0.02443 (10) 0.0258 (6)
H30 0.8119 −0.0556 0.0365 0.031*

Atomic displacement parameters (Å2)

U11 U22 U33 U12 U13 U23

O1 0.0130 (8) 0.0196 (9) 0.0326 (9) −0.0014 (8) −0.0031 (8) 0.0047 (8)
O2 0.0157 (9) 0.0261 (9) 0.0192 (8) 0.0022 (8) −0.0011 (7) −0.0020 (8)
C1 0.0173 (12) 0.0196 (13) 0.0163 (11) −0.0006 (11) −0.0021 (10) −0.0016 (10)
C2 0.0105 (11) 0.0241 (14) 0.0186 (11) −0.0027 (11) −0.0003 (9) −0.0010 (10)
C3 0.0148 (12) 0.0191 (13) 0.0167 (11) 0.0003 (11) −0.0027 (9) −0.0034 (10)
C4 0.0194 (12) 0.0205 (14) 0.0169 (11) −0.0013 (11) −0.0009 (10) −0.0009 (10)
C5 0.0140 (12) 0.0239 (14) 0.0205 (11) −0.0079 (11) 0.0009 (10) −0.0031 (11)



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sup-5

C6 0.0120 (12) 0.0251 (14) 0.0212 (11) 0.0015 (11) −0.0011 (10) −0.0029 (10)
C7 0.0157 (12) 0.0172 (12) 0.0197 (11) −0.0014 (11) −0.0002 (9) 0.0015 (10)
C8 0.0124 (12) 0.0159 (13) 0.0248 (12) 0.0032 (11) −0.0013 (10) −0.0007 (10)
C9 0.0142 (12) 0.0235 (14) 0.0236 (12) −0.0002 (11) −0.0026 (10) −0.0011 (11)
C10 0.0151 (12) 0.0131 (12) 0.0263 (12) −0.0042 (11) −0.0008 (10) −0.0006 (10)
C11 0.0214 (14) 0.0273 (14) 0.0293 (13) 0.0040 (12) −0.0024 (11) 0.0007 (12)
C12 0.0275 (15) 0.0305 (15) 0.0283 (13) 0.0014 (13) −0.0069 (12) 0.0050 (12)
C13 0.0319 (15) 0.0264 (14) 0.0226 (12) −0.0094 (13) 0.0003 (11) 0.0001 (11)
C14 0.0243 (14) 0.0334 (16) 0.0282 (13) −0.0034 (13) 0.0043 (11) −0.0058 (12)
C15 0.0186 (13) 0.0274 (14) 0.0266 (12) 0.0011 (12) −0.0021 (11) −0.0010 (11)
O3 0.0142 (9) 0.0208 (9) 0.0313 (9) 0.0014 (8) 0.0024 (7) 0.0046 (8)
O4 0.0149 (8) 0.0252 (9) 0.0198 (8) −0.0019 (8) 0.0012 (7) −0.0015 (7)
C16 0.0157 (12) 0.0163 (12) 0.0194 (11) −0.0012 (11) 0.0025 (10) −0.0034 (10)
C17 0.0137 (12) 0.0216 (14) 0.0204 (11) 0.0005 (11) −0.0003 (10) −0.0025 (10)
C18 0.0143 (12) 0.0183 (13) 0.0178 (11) −0.0012 (11) −0.0001 (9) −0.0036 (10)
C19 0.0198 (13) 0.0191 (14) 0.0227 (12) 0.0015 (11) 0.0001 (10) −0.0006 (10)
C20 0.0123 (12) 0.0244 (14) 0.0255 (12) −0.0001 (11) −0.0031 (10) −0.0018 (11)
C21 0.0136 (12) 0.0216 (13) 0.0211 (11) −0.0045 (11) 0.0017 (10) −0.0037 (10)
C22 0.0181 (12) 0.0167 (12) 0.0192 (11) −0.0018 (11) −0.0024 (10) 0.0012 (10)
C23 0.0146 (12) 0.0163 (12) 0.0235 (11) −0.0056 (11) 0.0025 (10) −0.0004 (10)
C24 0.0175 (13) 0.0263 (14) 0.0273 (13) −0.0031 (12) 0.0021 (11) −0.0024 (11)
C25 0.0137 (12) 0.0219 (13) 0.0239 (12) −0.0058 (11) 0.0033 (10) 0.0012 (10)
C26 0.0357 (16) 0.0253 (14) 0.0262 (13) −0.0008 (13) 0.0011 (12) −0.0013 (11)
C27 0.0452 (19) 0.0330 (16) 0.0318 (15) −0.0030 (14) −0.0044 (13) 0.0088 (14)
C28 0.0398 (17) 0.0419 (18) 0.0229 (13) −0.0148 (15) −0.0025 (13) 0.0022 (12)
C29 0.0343 (16) 0.0360 (16) 0.0272 (13) −0.0089 (14) 0.0029 (12) −0.0085 (12)
C30 0.0230 (14) 0.0271 (14) 0.0273 (13) −0.0030 (12) 0.0024 (11) −0.0026 (11)

Geometric parameters (Å, °)

O1—C1 1.371 (3) O3—C16 1.371 (3)
O1—H1O 0.8400 O3—H3O 0.8400
O2—C7 1.432 (3) O4—C22 1.432 (3)
O2—H2O 0.8400 O4—H4O 0.8400
C1—C2 1.382 (3) C16—C21 1.383 (3)
C1—C6 1.389 (4) C16—C17 1.384 (3)
C2—C3 1.394 (4) C17—C18 1.389 (3)
C2—H2 0.9500 C17—H17 0.9500
C3—C4 1.385 (3) C18—C19 1.388 (3)
C3—C7 1.520 (3) C18—C22 1.521 (3)
C4—C5 1.386 (3) C19—C20 1.383 (3)
C4—H4 0.9500 C19—H19 0.9500
C5—C6 1.387 (4) C20—C21 1.386 (4)
C5—H5 0.9500 C20—H20 0.9500
C6—H6 0.9500 C21—H21 0.9500
C7—C8 1.512 (3) C22—C23 1.516 (3)
C7—H7 1.0000 C22—H22 1.0000
C8—C9 1.327 (3) C23—C24 1.329 (3)
C8—C10 1.499 (3) C23—C25 1.488 (3)



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C9—H9A 0.9500 C24—H24A 0.9500
C9—H9B 0.9500 C24—H24B 0.9500
C10—C11 1.386 (3) C25—C30 1.388 (3)
C10—C15 1.387 (3) C25—C26 1.393 (4)
C11—C12 1.385 (4) C26—C27 1.386 (4)
C11—H11 0.9500 C26—H26 0.9500
C12—C13 1.374 (4) C27—C28 1.381 (4)
C12—H12 0.9500 C27—H27 0.9500
C13—C14 1.384 (4) C28—C29 1.368 (4)
C13—H13 0.9500 C28—H28 0.9500
C14—C15 1.384 (3) C29—C30 1.385 (4)
C14—H14 0.9500 C29—H29 0.9500
C15—H15 0.9500 C30—H30 0.9500

C1—O1—H1O 109.5 C16—O3—H3O 109.5
C7—O2—H2O 109.5 C22—O4—H4O 109.5
O1—C1—C2 122.1 (2) O3—C16—C21 118.3 (2)
O1—C1—C6 117.6 (2) O3—C16—C17 121.6 (2)
C2—C1—C6 120.3 (2) C21—C16—C17 120.1 (2)
C1—C2—C3 120.0 (2) C16—C17—C18 120.2 (2)
C1—C2—H2 120.0 C16—C17—H17 119.9
C3—C2—H2 120.0 C18—C17—H17 119.9
C4—C3—C2 119.8 (2) C19—C18—C17 119.7 (2)
C4—C3—C7 121.3 (2) C19—C18—C22 121.3 (2)
C2—C3—C7 118.9 (2) C17—C18—C22 119.0 (2)
C3—C4—C5 119.9 (2) C20—C19—C18 119.7 (2)
C3—C4—H4 120.0 C20—C19—H19 120.1
C5—C4—H4 120.0 C18—C19—H19 120.1
C4—C5—C6 120.5 (2) C19—C20—C21 120.6 (2)
C4—C5—H5 119.8 C19—C20—H20 119.7
C6—C5—H5 119.8 C21—C20—H20 119.7
C5—C6—C1 119.5 (2) C16—C21—C20 119.6 (2)
C5—C6—H6 120.3 C16—C21—H21 120.2
C1—C6—H6 120.3 C20—C21—H21 120.2
O2—C7—C8 108.83 (18) O4—C22—C23 109.16 (19)
O2—C7—C3 110.03 (18) O4—C22—C18 110.34 (18)
C8—C7—C3 111.52 (19) C23—C22—C18 110.42 (19)
O2—C7—H7 108.8 O4—C22—H22 109.0
C8—C7—H7 108.8 C23—C22—H22 109.0
C3—C7—H7 108.8 C18—C22—H22 109.0
C9—C8—C10 120.7 (2) C24—C23—C25 122.3 (2)
C9—C8—C7 122.8 (2) C24—C23—C22 121.4 (2)
C10—C8—C7 116.5 (2) C25—C23—C22 116.2 (2)
C8—C9—H9A 120.0 C23—C24—H24A 120.0
C8—C9—H9B 120.0 C23—C24—H24B 120.0
H9A—C9—H9B 120.0 H24A—C24—H24B 120.0
C11—C10—C15 118.7 (2) C30—C25—C26 117.7 (2)
C11—C10—C8 119.1 (2) C30—C25—C23 120.6 (2)
C15—C10—C8 122.2 (2) C26—C25—C23 121.7 (2)
C12—C11—C10 120.8 (2) C27—C26—C25 121.3 (3)



supplementary materials

sup-7

C12—C11—H11 119.6 C27—C26—H26 119.4
C10—C11—H11 119.6 C25—C26—H26 119.4
C13—C12—C11 120.1 (2) C28—C27—C26 119.8 (3)
C13—C12—H12 119.9 C28—C27—H27 120.1
C11—C12—H12 119.9 C26—C27—H27 120.1
C12—C13—C14 119.6 (2) C29—C28—C27 119.8 (2)
C12—C13—H13 120.2 C29—C28—H28 120.1
C14—C13—H13 120.2 C27—C28—H28 120.1
C15—C14—C13 120.3 (3) C28—C29—C30 120.5 (3)
C15—C14—H14 119.9 C28—C29—H29 119.7
C13—C14—H14 119.9 C30—C29—H29 119.7
C14—C15—C10 120.4 (2) C29—C30—C25 121.0 (3)
C14—C15—H15 119.8 C29—C30—H30 119.5
C10—C15—H15 119.8 C25—C30—H30 119.5

O1—C1—C2—C3 −179.59 (19) O3—C16—C17—C18 −178.75 (19)
C6—C1—C2—C3 0.4 (3) C21—C16—C17—C18 −0.2 (3)
C1—C2—C3—C4 −0.4 (3) C16—C17—C18—C19 −0.7 (3)
C1—C2—C3—C7 −179.8 (2) C16—C17—C18—C22 179.3 (2)
C2—C3—C4—C5 0.1 (3) C17—C18—C19—C20 1.1 (3)
C7—C3—C4—C5 179.4 (2) C22—C18—C19—C20 −179.0 (2)
C3—C4—C5—C6 0.3 (3) C18—C19—C20—C21 −0.4 (4)
C4—C5—C6—C1 −0.2 (3) O3—C16—C21—C20 179.43 (19)
O1—C1—C6—C5 179.91 (19) C17—C16—C21—C20 0.9 (3)
C2—C1—C6—C5 −0.1 (3) C19—C20—C21—C16 −0.5 (3)
C4—C3—C7—O2 −117.5 (2) C19—C18—C22—O4 132.6 (2)
C2—C3—C7—O2 61.8 (3) C17—C18—C22—O4 −47.4 (3)
C4—C3—C7—C8 121.6 (2) C19—C18—C22—C23 −106.6 (2)
C2—C3—C7—C8 −59.0 (3) C17—C18—C22—C23 73.3 (3)
O2—C7—C8—C9 −15.8 (3) O4—C22—C23—C24 15.4 (3)
C3—C7—C8—C9 105.8 (3) C18—C22—C23—C24 −106.1 (3)
O2—C7—C8—C10 163.3 (2) O4—C22—C23—C25 −167.12 (19)
C3—C7—C8—C10 −75.2 (3) C18—C22—C23—C25 71.4 (3)
C9—C8—C10—C11 65.5 (3) C24—C23—C25—C30 33.9 (4)
C7—C8—C10—C11 −113.6 (3) C22—C23—C25—C30 −143.6 (2)
C9—C8—C10—C15 −113.0 (3) C24—C23—C25—C26 −145.8 (3)
C7—C8—C10—C15 67.9 (3) C22—C23—C25—C26 36.8 (3)
C15—C10—C11—C12 0.1 (4) C30—C25—C26—C27 −0.6 (4)
C8—C10—C11—C12 −178.5 (2) C23—C25—C26—C27 179.1 (3)
C10—C11—C12—C13 0.6 (4) C25—C26—C27—C28 −0.7 (4)
C11—C12—C13—C14 −0.2 (4) C26—C27—C28—C29 1.1 (4)
C12—C13—C14—C15 −0.9 (4) C27—C28—C29—C30 −0.2 (4)
C13—C14—C15—C10 1.6 (4) C28—C29—C30—C25 −1.1 (4)
C11—C10—C15—C14 −1.2 (4) C26—C25—C30—C29 1.4 (4)
C8—C10—C15—C14 177.3 (2) C23—C25—C30—C29 −178.3 (2)

Hydrogen-bond geometry (Å, °)

D—H···A D—H H···A D···A D—H···A
C9—H9b···O2 0.95 2.39 2.726 (3) 101



supplementary materials

sup-8

C24—H24b···O4 0.95 2.34 2.708 (3) 102
O1—H1O···O4 0.84 1.89 2.727 (2) 175

O2—H2O···O1i 0.84 2.00 2.823 (2) 168

O3—H3O···O2ii 0.84 1.89 2.728 (2) 174

O4—H4O···O3iii 0.84 2.02 2.825 (2) 161
Symmetry codes: (i) −x+2, y+1/2, −z+1/2; (ii) x, y−1, z; (iii) −x+1, y+1/2, −z+1/2.



supplementary materials

sup-9

Fig. 1



supplementary materials

sup-10

Fig. 2



supplementary materials

sup-11

Fig. 3



supplementary materials

sup-12

Fig. 4