data reports

IUCrData (2019). 4, x191526 https://doi.org/10.1107/S2414314619015268 1 of 3

Ethyl 5-[(ethoxycarbonyl)oxy]-5,5-diphenylpent-2-
ynoate

Jorge A Cabezas* and Cristian Saul Campos Fernandez

Escuela de Quimica, Universidad de Costa Rica, 2060, San Pedro, San Jose, Costa Rica. *Correspondence e-mail:

jorge.cabezas@ucr.ac.cr

The title compound, C22H22O5, crystallizes with two molecules in the

asymmetric unit, one of which shows disorder of its ethyl acetate group over

two sets of sites in a 0.880 (2):0.120 (2) ratio. The C C distances in the two

molecules are almost the same [1.1939 (16) and 1.199 (2) Å], but the Csp3—

C C angles differ somewhat [175.92 (12) and 172.53 (16)�]. In the crystal,

several weak C—H� � �O interactions are seen.

Structure description

Highly functionalized homopropagyl alcohols are useful building blocks in organic

synthesis (Kim et al., 2017; Foley & Leighton, 2015; Francais et al., 2010; Hosseyni et al.,

2016; Gao et al., 2014; Trost & Rhee 2003; Yadav & Maiti, 2002). For instance, the title

compound, where the homopropargyl alcohol is masked as a carbonate, might serve as an

intermediate in the synthesis of �, �-unsaturated �-lactones The aim of this work is to

report the synthesis and crystal structure of the title compound.

The title compound crystallizes with two molecules in the asymmetric unit, as shown in

Fig. 1. The bond distances for the sp carbon-atom triple bonds are almost the same

[1.1939 (16) for C15 C16 and 1.199 (2) Å for C34 C35] but a greater difference is

present between the bond angles of C14—C15 C16 [175.92 (12)] and C33—C34 C35

[172.53 (16)�]. There is disorder in the ethyl ester grouping of the C20 molecule and

atoms C35, C36, O6 and C37 and their attached H atoms (if any) were modelled with two

sets of sites in a 0.880 (2):0.120 (2) ratio. In the crystal, several weak C—H� � �O inter-

actions occur (Table 1, Fig. 2).

Received 4 October 2019

Accepted 12 November 2019

Edited by W. T. A. Harrison, University of

Aberdeen, Scotland

Keywords: crystal structure; homopropargyl

alcohols; 1,3-dilithiopropyne; propargylation;

alkynes.

CCDC reference: 1901024

Structural data: full structural data are available

from iucrdata.iucr.org

ISSN 2414-3146

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2 of 3 Cabezas and Fernandez � C22H22O5 IUCrData (2019). 4, x191526

data reports

Synthesis and crystallization

The title compound, 1, was synthesized in a one-pot reaction

by the treatment of propargyl bromide, 2, with n-butyllithium

in the presence of TMEDA at �78�C to generate the

equivalent of 1,3-dilithiopropyne, 3, followed by addition of

benzophenone, 4; and after stirring overnight, the reaction

mixture was treated with ethyl chloroformate, 5, according to

the literature procedure (Cabezas et al., 2001) (Fig. 3). The

product was purified by column chromatography using

hexane-ether mixtures, and then recrystallized from ethyl

acetate solution.

Refinement

Crystal data, data collection and structure refinement are

summarized in Table 2.

Acknowledgements

We thank Dr Vojtech Jancik for crystallographic assistance.

Funding information

We acknowledge the Vicerrectorı́a de Investigación (UCR)

for financial support

Figure 2
The crystal packing of the title compound.

Figure 3
A synthetic scheme for the preparation of the title compound.

Table 2
Experimental details.

Crystal data
Chemical formula C22H22O5

Mr 366.39
Crystal system, space group Triclinic, P1
Temperature (K) 100
a, b, c (Å) 9.9461 (4), 12.1510 (5), 16.8171 (7)
�, �, � (�) 105.006 (1), 94.220 (1), 104.926 (1)
V (Å3) 1875.34 (13)
Z 4
Radiation type Mo K�
� (mm�1) 0.09
Crystal size (mm) 0.22 � 0.17 � 0.13

Data collection
Diffractometer Bruker D8 Venture
Absorption correction Multi-scan (SADABS; Bruker,

2015)
Tmin, Tmax 0.721, 0.746
No. of measured, independent and

observed [I > 2�(I)] reflections
54801, 8599, 7059

Rint 0.028
(sin �/�)max (�1) 0.650

Refinement
R[F 2 > 2�(F 2)], wR(F 2), S 0.036, 0.093, 1.02
No. of reflections 8599
No. of parameters 532
No. of restraints 186
H-atom treatment H-atom parameters constrained
�	max, �	min (e �3) 0.36, �0.25

Computer programs: APEX3 and SAINT (Bruker, 2015), SHELXT2014/5 (Sheldrick,
2015a), SHELXL2018/3 (Sheldrick, 2015b), shelXle (Hübschle et al., 2011), Mercury
(Macrae et al., 2006) and publCIF (Westrip, 2010).

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

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

C8—H8� � �O7 0.95 2.56 3.4079 (14) 149
C14—H14A� � �O7 0.99 2.61 3.4398 (14) 142
C18—H18A� � �O1i 0.99 2.62 3.4119 (15) 137
C31—H31� � �O1 0.95 2.43 3.3617 (15) 169
C33—H33B� � �O1 0.99 2.61 3.3008 (13) 127

Symmetry code: (i) �x þ 2;�yþ 1;�zþ 2.

Figure 1
The title molecule with 50% probability ellipsoids. The minor disorder
component for the C20 molecule is not shown.



data reports

IUCrData (2019). 4, x191526 Cabezas and Fernandez � C22H22O5 3 of 3

References

Bruker (2015). APEX3, SAINT and SADABS. Bruker AXS Inc.,
Madison, Wisconsin, USA.

Cabezas, J. A., Pereira, A. & Amey, A. (2001). Tetrahedron Lett. 42,
6819–6822.

Foley, C. N. & Leighton, J. L. (2015). Org. Lett. 17, 5858–5861.
Francais, A., Leyva, A., Etxebarria-Jardi, G. & Ley, S. V. (2010). Org.

Lett. 12, 340–343.
Gao, P., Li, H. X., Hao, X. H., Jin, D. P., Chen, D. Q., Yan, X. B., Wu,

X. X., Song, X. R., Liu, X. Y. & Liang, Y. M. (2014). Org. Lett. 16,
6298–6301.

Hosseyni, S., Wojtas, L., Li, M. & Shi, X. (2016). J. Am. Chem. Soc.
138, 3994–3997.

Hübschle, C. B., Sheldrick, G. M. & Dittrich, B. (2011). J. Appl. Cryst.
44, 1281–1284.

Kim, J., Jeong, W. & Rhee, Y. H. (2017). Org. Lett. 19, 242–245.
Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P.,

Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39,
453–457.

Sheldrick, G. M. (2015a). Acta Cryst. A71, 3–8.
Sheldrick, G. M. (2015b). Acta Cryst. C71, 3–8.
Trost, B. M. & Rhee, Y. H. (2003). J. Am. Chem. Soc. 125, 7482–7483.
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925.
Yadav, J. S. & Maiti, A. (2002). Tetrahedron, 58, 4955–4961.

http://scripts.iucr.org/cgi-bin/cr.cgi?rm=pdfbb&cnor=hb4323&bbid=BB1
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http://scripts.iucr.org/cgi-bin/cr.cgi?rm=pdfbb&cnor=hb4323&bbid=BB14
http://scripts.iucr.org/cgi-bin/cr.cgi?rm=pdfbb&cnor=hb4323&bbid=BB15


data reports

data-1IUCrData (2019). 4, x191526    

full crystallographic data

IUCrData (2019). 4, x191526    [https://doi.org/10.1107/S2414314619015268]

Ethyl 5-[(ethoxycarbonyl)oxy]-5,5-diphenylpent-2-ynoate

Jorge A Cabezas and Cristian Saul Campos Fernandez

Ethyl 5-[(ethoxycarbonyl)oxy]-5,5-diphenylpent-2-ynoate 

Crystal data 

C22H22O5

Mr = 366.39
Triclinic, P1
a = 9.9461 (4) Å
b = 12.1510 (5) Å
c = 16.8171 (7) Å
α = 105.006 (1)°
β = 94.220 (1)°
γ = 104.926 (1)°
V = 1875.34 (13) Å3

Z = 4
F(000) = 776
Dx = 1.298 Mg m−3

Mo Kα radiation, λ = 0.71073 Å
Cell parameters from 9767 reflections
θ = 2.8–27.5°
µ = 0.09 mm−1

T = 100 K
Block, light yellow
0.22 × 0.17 × 0.13 mm

Data collection 

Bruker D8 Venture 
diffractometer

Radiation source: Incoatec Microsource
Detector resolution: 10.4167 pixels mm-1

ω scans
Absorption correction: multi-scan 

(SADABS; Bruker, 2015)
Tmin = 0.721, Tmax = 0.746

54801 measured reflections
8599 independent reflections
7059 reflections with I > 2σ(I)
Rint = 0.028
θmax = 27.5°, θmin = 2.6°
h = −12→12
k = −15→15
l = −21→21

Refinement 

Refinement on F2

Least-squares matrix: full
R[F2 > 2σ(F2)] = 0.036
wR(F2) = 0.093
S = 1.02
8599 reflections
532 parameters
186 restraints
Primary atom site location: structure-invariant 

direct methods

Secondary atom site location: difference Fourier 
map

Hydrogen site location: inferred from 
neighbouring sites

H-atom parameters constrained
w = 1/[σ2(Fo

2) + (0.0454P)2 + 0.5843P] 
where P = (Fo

2 + 2Fc
2)/3

(Δ/σ)max = 0.001
Δρmax = 0.36 e Å−3

Δρmin = −0.24 e Å−3

Special details 

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



data reports

data-2IUCrData (2019). 4, x191526    

Refinement. All H atoms were located initially by difference Fourier synthesis and then relocated to idealized locations 
for refinement as riding atoms.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) 

x y z Uiso*/Ueq Occ. (<1)

O1 0.81699 (8) 0.40080 (8) 0.89228 (5) 0.02350 (19)
C1 0.27160 (11) −0.01485 (10) 0.83753 (7) 0.0148 (2)
O2 0.77716 (8) 0.29149 (7) 0.98210 (5) 0.01976 (18)
C2 0.38374 (12) −0.03498 (10) 0.88071 (7) 0.0189 (2)
H2 0.436404 0.023699 0.929750 0.023*
O3 0.28485 (8) 0.14591 (7) 0.95391 (5) 0.01491 (16)
C3 0.41879 (13) −0.14048 (11) 0.85231 (8) 0.0231 (3)
H3 0.494787 −0.153900 0.882312 0.028*
O4 0.25585 (8) 0.32945 (7) 0.96811 (5) 0.02070 (18)
C4 0.34348 (13) −0.22619 (10) 0.78046 (8) 0.0234 (3)
H4 0.368287 −0.297905 0.760986 0.028*
O5 0.34124 (8) 0.27211 (7) 1.07449 (5) 0.01890 (17)
C5 0.23196 (13) −0.20709 (10) 0.73711 (8) 0.0222 (2)
H5 0.180079 −0.265766 0.687853 0.027*
C6 0.19596 (12) −0.10203 (10) 0.76568 (7) 0.0184 (2)
H6 0.118989 −0.089543 0.735906 0.022*
C7 0.07917 (11) 0.08796 (9) 0.84860 (7) 0.0144 (2)
C8 0.01672 (12) 0.12322 (10) 0.78644 (7) 0.0178 (2)
H8 0.072736 0.159065 0.751442 0.021*
O8 0.70969 (8) 0.34032 (7) 0.55046 (5) 0.01559 (16)
C9 −0.12827 (12) 0.10579 (10) 0.77571 (7) 0.0202 (2)
H9 −0.170739 0.129795 0.733164 0.024*
O9 0.74620 (9) 0.16970 (7) 0.56704 (5) 0.02059 (18)
C11 −0.14925 (12) 0.01679 (11) 0.88751 (7) 0.0210 (2)
H11 −0.205526 −0.019704 0.922125 0.025*
C10 −0.21110 (12) 0.05387 (10) 0.82637 (7) 0.0204 (2)
H10 −0.309631 0.043666 0.819345 0.024*
O10 0.63254 (9) 0.18044 (7) 0.44917 (5) 0.01925 (17)
C13 0.23688 (11) 0.10354 (9) 0.86421 (6) 0.0138 (2)
C12 −0.00532 (12) 0.03314 (10) 0.89790 (7) 0.0184 (2)
H12 0.036339 0.006570 0.939264 0.022*
C14 0.32186 (11) 0.18946 (10) 0.81982 (7) 0.0153 (2)
H14A 0.310036 0.147821 0.759660 0.018*
H14B 0.283466 0.258206 0.825833 0.018*
C16 0.59229 (12) 0.27350 (10) 0.88425 (7) 0.0174 (2)
C15 0.47165 (11) 0.23273 (10) 0.85321 (7) 0.0160 (2)
C17 0.73983 (11) 0.32921 (10) 0.91892 (7) 0.0167 (2)
C18 0.92621 (12) 0.33846 (12) 1.01716 (8) 0.0260 (3)
H18A 0.952370 0.426111 1.039938 0.031*
H18B 0.984914 0.318049 0.973701 0.031*
C19 0.94828 (14) 0.28291 (13) 1.08508 (8) 0.0295 (3)
H19A 0.917726 0.196104 1.062224 0.044*



data reports

data-3IUCrData (2019). 4, x191526    

H19B 0.893208 0.307004 1.128952 0.044*
H19C 1.048331 0.309309 1.108453 0.044*
C20 0.73795 (11) 0.52715 (10) 0.64707 (7) 0.0153 (2)
C21 0.82971 (12) 0.62948 (10) 0.70272 (7) 0.0190 (2)
H21 0.915297 0.625844 0.729476 0.023*
C22 0.79681 (13) 0.73670 (10) 0.71929 (8) 0.0228 (3)
H22 0.859448 0.805802 0.757828 0.027*
C23 0.67345 (13) 0.74343 (11) 0.68001 (8) 0.0230 (3)
H23 0.650630 0.816698 0.692060 0.028*
C24 0.58307 (13) 0.64285 (11) 0.62293 (8) 0.0232 (3)
H24 0.499279 0.647760 0.594908 0.028*
C25 0.61448 (12) 0.53500 (10) 0.60654 (7) 0.0190 (2)
H25 0.551812 0.466300 0.567642 0.023*
C26 0.92255 (11) 0.41887 (9) 0.65338 (7) 0.0163 (2)
C27 1.00433 (13) 0.44168 (12) 0.59285 (8) 0.0259 (3)
H27 0.961109 0.445615 0.541776 0.031*
C28 1.14856 (14) 0.45879 (12) 0.60613 (9) 0.0319 (3)
H28 1.203468 0.474016 0.564177 0.038*
C29 1.21224 (13) 0.45368 (11) 0.68038 (9) 0.0291 (3)
H29 1.310988 0.465572 0.689682 0.035*
C30 1.13185 (13) 0.43123 (11) 0.74099 (9) 0.0267 (3)
H30 1.175639 0.427590 0.792012 0.032*
C31 0.98712 (12) 0.41386 (10) 0.72797 (8) 0.0217 (2)
H31 0.932545 0.398593 0.770051 0.026*
C32 0.76597 (11) 0.40682 (9) 0.63736 (7) 0.0141 (2)
C33 0.68114 (11) 0.34551 (10) 0.69605 (7) 0.0150 (2)
H33A 0.719010 0.280635 0.703897 0.018*
H33B 0.692982 0.404137 0.751197 0.018*
C34 0.53171 (12) 0.29679 (10) 0.66250 (7) 0.0158 (2)
O7 0.17896 (8) 0.13603 (8) 0.61612 (5) 0.02321 (19)
O6 0.26944 (9) 0.16917 (9) 0.50205 (6) 0.0206 (2) 0.880 (2)
C35 0.4135 (2) 0.2486 (3) 0.62745 (19) 0.0171 (5) 0.880 (2)
C36 0.27374 (17) 0.17945 (14) 0.58293 (10) 0.0169 (4) 0.880 (2)
C37 0.13761 (18) 0.09582 (16) 0.44892 (11) 0.0230 (4) 0.880 (2)
H37A 0.099484 0.025072 0.468075 0.028* 0.880 (2)
H37B 0.155490 0.067932 0.391025 0.028* 0.880 (2)
C38 0.03124 (16) 0.16443 (14) 0.45078 (9) 0.0276 (3) 0.880 (2)
H38A 0.008023 0.186784 0.507262 0.041* 0.880 (2)
H38B −0.054173 0.114859 0.412056 0.041* 0.880 (2)
H38C 0.070539 0.236371 0.434222 0.041* 0.880 (2)
O6A 0.2498 (7) 0.2460 (7) 0.5284 (4) 0.0205 (12) 0.120 (2)
C35A 0.4113 (15) 0.266 (3) 0.6382 (17) 0.0171 (5) 0.120 (2)
C36A 0.2675 (13) 0.2105 (12) 0.5967 (8) 0.0185 (14) 0.120 (2)
C37A 0.1103 (11) 0.1935 (9) 0.4795 (6) 0.0259 (15) 0.120 (2)
H37C 0.091324 0.245720 0.446239 0.031* 0.120 (2)
H37D 0.038483 0.185552 0.517038 0.031* 0.120 (2)
C38A 0.1017 (16) 0.0761 (13) 0.4239 (9) 0.031 (3) 0.120 (2)
H38D 0.176341 0.083822 0.389005 0.046* 0.120 (2)



data reports

data-4IUCrData (2019). 4, x191526    

H38E 0.009810 0.043031 0.388383 0.046* 0.120 (2)
H38F 0.113397 0.022896 0.457184 0.046* 0.120 (2)
C39 0.29032 (11) 0.25774 (10) 0.99560 (7) 0.0157 (2)
C40 0.38139 (13) 0.39366 (10) 1.12861 (7) 0.0221 (2)
H40A 0.378894 0.393053 1.187235 0.026*
H40B 0.313650 0.435068 1.114143 0.026*
C41 0.52676 (13) 0.45870 (11) 1.11907 (9) 0.0285 (3)
H41A 0.526216 0.467934 1.062873 0.043*
H41B 0.592009 0.413303 1.127947 0.043*
H41C 0.556999 0.537323 1.160174 0.043*
C42 0.70128 (11) 0.22392 (10) 0.52654 (7) 0.0156 (2)
C43 0.61129 (12) 0.05383 (10) 0.41182 (7) 0.0196 (2)
H43A 0.587446 0.009968 0.453347 0.024*
H43B 0.697986 0.039704 0.391396 0.024*
C44 0.49251 (12) 0.01266 (10) 0.34075 (7) 0.0209 (2)
H44A 0.516001 0.058708 0.301126 0.031*
H44B 0.406551 0.024303 0.362050 0.031*
H44C 0.477412 −0.071917 0.312674 0.031*

Atomic displacement parameters (Å2) 

U11 U22 U33 U12 U13 U23

O1 0.0173 (4) 0.0282 (5) 0.0221 (4) −0.0020 (3) −0.0007 (3) 0.0120 (4)
C1 0.0136 (5) 0.0152 (5) 0.0168 (5) 0.0033 (4) 0.0045 (4) 0.0067 (4)
O2 0.0137 (4) 0.0241 (4) 0.0211 (4) 0.0017 (3) −0.0010 (3) 0.0105 (3)
C2 0.0170 (5) 0.0187 (6) 0.0214 (6) 0.0053 (4) 0.0012 (4) 0.0070 (5)
O3 0.0157 (4) 0.0148 (4) 0.0131 (4) 0.0039 (3) −0.0009 (3) 0.0034 (3)
C3 0.0209 (6) 0.0223 (6) 0.0310 (7) 0.0097 (5) 0.0046 (5) 0.0122 (5)
O4 0.0212 (4) 0.0190 (4) 0.0229 (4) 0.0081 (3) 0.0009 (3) 0.0060 (3)
C4 0.0248 (6) 0.0158 (6) 0.0325 (7) 0.0077 (5) 0.0114 (5) 0.0084 (5)
O5 0.0208 (4) 0.0172 (4) 0.0155 (4) 0.0038 (3) −0.0017 (3) 0.0019 (3)
C5 0.0224 (6) 0.0175 (6) 0.0226 (6) 0.0018 (5) 0.0054 (5) 0.0023 (5)
C6 0.0159 (5) 0.0192 (6) 0.0188 (6) 0.0031 (4) 0.0020 (4) 0.0053 (5)
C7 0.0123 (5) 0.0131 (5) 0.0159 (5) 0.0029 (4) 0.0010 (4) 0.0020 (4)
C8 0.0152 (5) 0.0183 (5) 0.0202 (6) 0.0035 (4) 0.0014 (4) 0.0075 (5)
O8 0.0189 (4) 0.0138 (4) 0.0133 (4) 0.0048 (3) 0.0007 (3) 0.0029 (3)
C9 0.0173 (6) 0.0191 (6) 0.0232 (6) 0.0062 (4) −0.0028 (4) 0.0053 (5)
O9 0.0237 (4) 0.0195 (4) 0.0203 (4) 0.0101 (3) 0.0006 (3) 0.0056 (3)
C11 0.0167 (6) 0.0226 (6) 0.0209 (6) 0.0017 (5) 0.0055 (4) 0.0049 (5)
C10 0.0119 (5) 0.0190 (6) 0.0254 (6) 0.0038 (4) 0.0006 (4) −0.0007 (5)
O10 0.0259 (4) 0.0146 (4) 0.0159 (4) 0.0070 (3) −0.0010 (3) 0.0021 (3)
C13 0.0127 (5) 0.0151 (5) 0.0126 (5) 0.0027 (4) −0.0002 (4) 0.0044 (4)
C12 0.0172 (5) 0.0208 (6) 0.0165 (5) 0.0038 (4) 0.0011 (4) 0.0060 (4)
C14 0.0125 (5) 0.0173 (5) 0.0167 (5) 0.0026 (4) 0.0008 (4) 0.0077 (4)
C16 0.0173 (6) 0.0176 (5) 0.0184 (5) 0.0042 (4) 0.0029 (4) 0.0077 (4)
C15 0.0164 (6) 0.0156 (5) 0.0168 (5) 0.0041 (4) 0.0032 (4) 0.0064 (4)
C17 0.0152 (5) 0.0178 (5) 0.0161 (5) 0.0039 (4) 0.0013 (4) 0.0041 (4)
C18 0.0128 (6) 0.0373 (7) 0.0255 (6) 0.0000 (5) −0.0031 (5) 0.0139 (6)



data reports

data-5IUCrData (2019). 4, x191526    

C19 0.0224 (6) 0.0400 (8) 0.0258 (7) 0.0054 (6) −0.0029 (5) 0.0144 (6)
C20 0.0164 (5) 0.0156 (5) 0.0153 (5) 0.0050 (4) 0.0042 (4) 0.0058 (4)
C21 0.0172 (5) 0.0185 (6) 0.0202 (6) 0.0042 (4) 0.0019 (4) 0.0049 (5)
C22 0.0243 (6) 0.0153 (6) 0.0256 (6) 0.0026 (5) 0.0051 (5) 0.0033 (5)
C23 0.0281 (6) 0.0167 (6) 0.0289 (6) 0.0101 (5) 0.0094 (5) 0.0091 (5)
C24 0.0234 (6) 0.0242 (6) 0.0266 (6) 0.0115 (5) 0.0026 (5) 0.0106 (5)
C25 0.0196 (6) 0.0173 (5) 0.0191 (6) 0.0049 (4) −0.0001 (4) 0.0050 (4)
C26 0.0143 (5) 0.0121 (5) 0.0216 (6) 0.0039 (4) 0.0020 (4) 0.0033 (4)
C27 0.0203 (6) 0.0305 (7) 0.0258 (6) 0.0042 (5) 0.0050 (5) 0.0089 (5)
C28 0.0201 (6) 0.0345 (7) 0.0376 (8) 0.0037 (5) 0.0124 (5) 0.0063 (6)
C29 0.0137 (6) 0.0211 (6) 0.0471 (8) 0.0046 (5) 0.0026 (5) 0.0017 (6)
C30 0.0181 (6) 0.0227 (6) 0.0369 (7) 0.0045 (5) −0.0049 (5) 0.0085 (5)
C31 0.0172 (6) 0.0205 (6) 0.0270 (6) 0.0037 (5) 0.0010 (5) 0.0086 (5)
C32 0.0135 (5) 0.0141 (5) 0.0133 (5) 0.0027 (4) 0.0001 (4) 0.0032 (4)
C33 0.0137 (5) 0.0162 (5) 0.0152 (5) 0.0040 (4) 0.0011 (4) 0.0051 (4)
C34 0.0176 (5) 0.0158 (5) 0.0168 (5) 0.0065 (4) 0.0045 (4) 0.0072 (4)
O7 0.0169 (4) 0.0292 (5) 0.0237 (4) 0.0031 (3) 0.0045 (3) 0.0111 (4)
O6 0.0144 (4) 0.0276 (6) 0.0172 (5) 0.0016 (4) 0.0014 (3) 0.0067 (4)
C35 0.0172 (6) 0.0184 (12) 0.0182 (11) 0.0069 (5) 0.0042 (5) 0.0074 (8)
C36 0.0145 (6) 0.0179 (8) 0.0198 (8) 0.0068 (6) 0.0024 (5) 0.0059 (6)
C37 0.0173 (9) 0.0275 (9) 0.0179 (9) 0.0005 (7) −0.0004 (6) 0.0027 (7)
C38 0.0198 (8) 0.0376 (9) 0.0235 (7) 0.0063 (6) −0.0009 (6) 0.0084 (6)
O6A 0.0176 (19) 0.023 (2) 0.0191 (19) 0.0049 (18) −0.0009 (17) 0.0056 (17)
C35A 0.0172 (6) 0.0184 (12) 0.0182 (11) 0.0069 (5) 0.0042 (5) 0.0074 (8)
C36A 0.018 (2) 0.021 (2) 0.018 (2) 0.007 (2) 0.002 (2) 0.008 (2)
C37A 0.019 (2) 0.032 (2) 0.022 (2) 0.003 (2) −0.003 (2) 0.006 (2)
C38A 0.023 (4) 0.037 (4) 0.021 (4) −0.002 (4) −0.002 (4) 0.002 (4)
C39 0.0111 (5) 0.0167 (5) 0.0177 (5) 0.0023 (4) 0.0023 (4) 0.0039 (4)
C40 0.0255 (6) 0.0176 (6) 0.0179 (6) 0.0051 (5) −0.0007 (5) −0.0016 (5)
C41 0.0249 (6) 0.0213 (6) 0.0349 (7) 0.0014 (5) −0.0050 (5) 0.0086 (5)
C42 0.0143 (5) 0.0163 (5) 0.0165 (5) 0.0049 (4) 0.0041 (4) 0.0039 (4)
C43 0.0249 (6) 0.0144 (5) 0.0188 (6) 0.0077 (5) 0.0020 (5) 0.0019 (4)
C44 0.0224 (6) 0.0157 (6) 0.0219 (6) 0.0037 (5) 0.0006 (5) 0.0032 (5)

Geometric parameters (Å, º) 

O1—C17 1.2062 (14) C23—C24 1.3866 (18)
C1—C6 1.3933 (16) C23—H23 0.9500
C1—C2 1.3943 (15) C24—C25 1.3883 (16)
C1—C13 1.5279 (15) C24—H24 0.9500
O2—C17 1.3261 (13) C25—H25 0.9500
O2—C18 1.4603 (14) C26—C27 1.3879 (17)
C2—C3 1.3895 (16) C26—C31 1.3896 (16)
C2—H2 0.9500 C26—C32 1.5230 (15)
O3—C39 1.3431 (13) C27—C28 1.3878 (18)
O3—C13 1.4608 (13) C27—H27 0.9500
C3—C4 1.3852 (18) C28—C29 1.381 (2)
C3—H3 0.9500 C28—H28 0.9500



data reports

data-6IUCrData (2019). 4, x191526    

O4—C39 1.1957 (13) C29—C30 1.380 (2)
C4—C5 1.3845 (18) C29—H29 0.9500
C4—H4 0.9500 C30—C31 1.3921 (16)
O5—C39 1.3353 (13) C30—H30 0.9500
O5—C40 1.4545 (13) C31—H31 0.9500
C5—C6 1.3899 (16) C32—C33 1.5558 (15)
C5—H5 0.9500 C33—C34 1.4588 (15)
C6—H6 0.9500 C33—H33A 0.9900
C7—C8 1.3912 (15) C33—H33B 0.9900
C7—C12 1.3919 (15) C34—C35A 1.166 (13)
C7—C13 1.5251 (14) C34—C35 1.199 (2)
C8—C9 1.3934 (16) O7—C36 1.2052 (18)
C8—H8 0.9500 O7—C36A 1.219 (12)
O8—C42 1.3450 (13) O6—C36 1.3297 (18)
O8—C32 1.4620 (13) O6—C37 1.4577 (18)
C9—C10 1.3843 (17) C35—C36 1.455 (2)
C9—H9 0.9500 C37—C38 1.504 (2)
O9—C42 1.1986 (14) C37—H37A 0.9900
C11—C12 1.3850 (16) C37—H37B 0.9900
C11—C10 1.3887 (17) C38—H38A 0.9800
C11—H11 0.9500 C38—H38B 0.9800
C10—H10 0.9500 C38—H38C 0.9800
O10—C42 1.3292 (13) O6A—C36A 1.343 (12)
O10—C43 1.4556 (13) O6A—C37A 1.453 (11)
C13—C14 1.5504 (14) C35A—C36A 1.448 (14)
C12—H12 0.9500 C37A—C38A 1.468 (14)
C14—C15 1.4601 (15) C37A—H37C 0.9900
C14—H14A 0.9900 C37A—H37D 0.9900
C14—H14B 0.9900 C38A—H38D 0.9800
C16—C15 1.1939 (16) C38A—H38E 0.9800
C16—C17 1.4524 (15) C38A—H38F 0.9800
C18—C19 1.4989 (17) C40—C41 1.5006 (18)
C18—H18A 0.9900 C40—H40A 0.9900
C18—H18B 0.9900 C40—H40B 0.9900
C19—H19A 0.9800 C41—H41A 0.9800
C19—H19B 0.9800 C41—H41B 0.9800
C19—H19C 0.9800 C41—H41C 0.9800
C20—C21 1.3935 (16) C43—C44 1.5008 (16)
C20—C25 1.3973 (15) C43—H43A 0.9900
C20—C32 1.5281 (15) C43—H43B 0.9900
C21—C22 1.3882 (16) C44—H44A 0.9800
C21—H21 0.9500 C44—H44B 0.9800
C22—C23 1.3817 (18) C44—H44C 0.9800
C22—H22 0.9500

C6—C1—C2 118.89 (10) C28—C27—H27 119.6
C6—C1—C13 119.69 (10) C26—C27—H27 119.6
C2—C1—C13 121.30 (10) C29—C28—C27 119.97 (12)



data reports

data-7IUCrData (2019). 4, x191526    

C17—O2—C18 114.95 (9) C29—C28—H28 120.0
C3—C2—C1 120.29 (11) C27—C28—H28 120.0
C3—C2—H2 119.9 C30—C29—C28 119.74 (12)
C1—C2—H2 119.9 C30—C29—H29 120.1
C39—O3—C13 119.10 (8) C28—C29—H29 120.1
C4—C3—C2 120.33 (11) C29—C30—C31 120.54 (12)
C4—C3—H3 119.8 C29—C30—H30 119.7
C2—C3—H3 119.8 C31—C30—H30 119.7
C5—C4—C3 119.85 (11) C26—C31—C30 119.95 (12)
C5—C4—H4 120.1 C26—C31—H31 120.0
C3—C4—H4 120.1 C30—C31—H31 120.0
C39—O5—C40 115.48 (9) O8—C32—C26 109.63 (8)
C4—C5—C6 119.97 (11) O8—C32—C20 104.17 (8)
C4—C5—H5 120.0 C26—C32—C20 112.04 (9)
C6—C5—H5 120.0 O8—C32—C33 109.97 (8)
C5—C6—C1 120.67 (11) C26—C32—C33 112.54 (9)
C5—C6—H6 119.7 C20—C32—C33 108.15 (9)
C1—C6—H6 119.7 C34—C33—C32 111.71 (9)
C8—C7—C12 119.15 (10) C34—C33—H33A 109.3
C8—C7—C13 123.00 (10) C32—C33—H33A 109.3
C12—C7—C13 117.84 (9) C34—C33—H33B 109.3
C7—C8—C9 119.76 (11) C32—C33—H33B 109.3
C7—C8—H8 120.1 H33A—C33—H33B 107.9
C9—C8—H8 120.1 C35A—C34—C33 175.3 (14)
C42—O8—C32 117.61 (8) C35—C34—C33 172.53 (16)
C10—C9—C8 120.72 (11) C36—O6—C37 116.13 (12)
C10—C9—H9 119.6 C34—C35—C36 174.5 (3)
C8—C9—H9 119.6 O7—C36—O6 126.34 (14)
C12—C11—C10 119.83 (11) O7—C36—C35 123.46 (19)
C12—C11—H11 120.1 O6—C36—C35 110.17 (18)
C10—C11—H11 120.1 O6—C37—C38 111.08 (14)
C9—C10—C11 119.58 (10) O6—C37—H37A 109.4
C9—C10—H10 120.2 C38—C37—H37A 109.4
C11—C10—H10 120.2 O6—C37—H37B 109.4
C42—O10—C43 115.04 (9) C38—C37—H37B 109.4
O3—C13—C7 108.81 (8) H37A—C37—H37B 108.0
O3—C13—C1 103.54 (8) C37—C38—H38A 109.5
C7—C13—C1 112.21 (9) C37—C38—H38B 109.5
O3—C13—C14 110.73 (8) H38A—C38—H38B 109.5
C7—C13—C14 112.37 (9) C37—C38—H38C 109.5
C1—C13—C14 108.83 (9) H38A—C38—H38C 109.5
C11—C12—C7 120.93 (11) H38B—C38—H38C 109.5
C11—C12—H12 119.5 C36A—O6A—C37A 114.6 (8)
C7—C12—H12 119.5 C34—C35A—C36A 170 (2)
C15—C14—C13 112.62 (9) O7—C36A—O6A 124.6 (10)
C15—C14—H14A 109.1 O7—C36A—C35A 125.9 (15)
C13—C14—H14A 109.1 O6A—C36A—C35A 109.3 (15)
C15—C14—H14B 109.1 O6A—C37A—C38A 109.6 (10)



data reports

data-8IUCrData (2019). 4, x191526    

C13—C14—H14B 109.1 O6A—C37A—H37C 109.8
H14A—C14—H14B 107.8 C38A—C37A—H37C 109.8
C15—C16—C17 176.04 (12) O6A—C37A—H37D 109.8
C16—C15—C14 175.92 (12) C38A—C37A—H37D 109.8
O1—C17—O2 125.22 (10) H37C—C37A—H37D 108.2
O1—C17—C16 122.99 (10) C37A—C38A—H38D 109.5
O2—C17—C16 111.78 (9) C37A—C38A—H38E 109.5
O2—C18—C19 106.98 (10) H38D—C38A—H38E 109.5
O2—C18—H18A 110.3 C37A—C38A—H38F 109.5
C19—C18—H18A 110.3 H38D—C38A—H38F 109.5
O2—C18—H18B 110.3 H38E—C38A—H38F 109.5
C19—C18—H18B 110.3 O4—C39—O5 127.00 (10)
H18A—C18—H18B 108.6 O4—C39—O3 127.29 (10)
C18—C19—H19A 109.5 O5—C39—O3 105.70 (9)
C18—C19—H19B 109.5 O5—C40—C41 110.11 (10)
H19A—C19—H19B 109.5 O5—C40—H40A 109.6
C18—C19—H19C 109.5 C41—C40—H40A 109.6
H19A—C19—H19C 109.5 O5—C40—H40B 109.6
H19B—C19—H19C 109.5 C41—C40—H40B 109.6
C21—C20—C25 118.95 (10) H40A—C40—H40B 108.2
C21—C20—C32 119.96 (10) C40—C41—H41A 109.5
C25—C20—C32 120.84 (10) C40—C41—H41B 109.5
C22—C21—C20 120.41 (11) H41A—C41—H41B 109.5
C22—C21—H21 119.8 C40—C41—H41C 109.5
C20—C21—H21 119.8 H41A—C41—H41C 109.5
C23—C22—C21 120.34 (11) H41B—C41—H41C 109.5
C23—C22—H22 119.8 O9—C42—O10 126.63 (10)
C21—C22—H22 119.8 O9—C42—O8 126.88 (10)
C22—C23—C24 119.75 (11) O10—C42—O8 106.49 (9)
C22—C23—H23 120.1 O10—C43—C44 107.14 (9)
C24—C23—H23 120.1 O10—C43—H43A 110.3
C23—C24—C25 120.30 (11) C44—C43—H43A 110.3
C23—C24—H24 119.9 O10—C43—H43B 110.3
C25—C24—H24 119.9 C44—C43—H43B 110.3
C24—C25—C20 120.23 (11) H43A—C43—H43B 108.5
C24—C25—H25 119.9 C43—C44—H44A 109.5
C20—C25—H25 119.9 C43—C44—H44B 109.5
C27—C26—C31 119.08 (11) H44A—C44—H44B 109.5
C27—C26—C32 118.58 (10) C43—C44—H44C 109.5
C31—C26—C32 122.26 (10) H44A—C44—H44C 109.5
C28—C27—C26 120.73 (12) H44B—C44—H44C 109.5

C6—C1—C2—C3 −0.11 (17) C31—C26—C27—C28 0.28 (18)
C13—C1—C2—C3 −175.99 (10) C32—C26—C27—C28 177.03 (11)
C1—C2—C3—C4 0.57 (18) C26—C27—C28—C29 −0.3 (2)
C2—C3—C4—C5 −0.55 (18) C27—C28—C29—C30 0.2 (2)
C3—C4—C5—C6 0.07 (18) C28—C29—C30—C31 −0.10 (19)
C4—C5—C6—C1 0.39 (17) C27—C26—C31—C30 −0.21 (17)



data reports

data-9IUCrData (2019). 4, x191526    

C2—C1—C6—C5 −0.37 (17) C32—C26—C31—C30 −176.84 (10)
C13—C1—C6—C5 175.58 (10) C29—C30—C31—C26 0.12 (18)
C12—C7—C8—C9 1.47 (17) C42—O8—C32—C26 69.26 (11)
C13—C7—C8—C9 179.81 (10) C42—O8—C32—C20 −170.67 (8)
C7—C8—C9—C10 0.12 (17) C42—O8—C32—C33 −54.98 (11)
C8—C9—C10—C11 −1.20 (18) C27—C26—C32—O8 40.24 (13)
C12—C11—C10—C9 0.68 (17) C31—C26—C32—O8 −143.12 (10)
C39—O3—C13—C7 −70.88 (11) C27—C26—C32—C20 −74.91 (13)
C39—O3—C13—C1 169.59 (8) C31—C26—C32—C20 101.74 (12)
C39—O3—C13—C14 53.10 (12) C27—C26—C32—C33 162.96 (10)
C8—C7—C13—O3 137.44 (10) C31—C26—C32—C33 −20.40 (14)
C12—C7—C13—O3 −44.20 (12) C21—C20—C32—O8 −148.68 (10)
C8—C7—C13—C1 −108.59 (12) C25—C20—C32—O8 37.21 (13)
C12—C7—C13—C1 69.77 (12) C21—C20—C32—C26 −30.25 (14)
C8—C7—C13—C14 14.44 (15) C25—C20—C32—C26 155.64 (10)
C12—C7—C13—C14 −167.19 (10) C21—C20—C32—C33 94.36 (11)
C6—C1—C13—O3 155.22 (9) C25—C20—C32—C33 −79.75 (12)
C2—C1—C13—O3 −28.94 (13) O8—C32—C33—C34 −37.14 (12)
C6—C1—C13—C7 38.05 (13) C26—C32—C33—C34 −159.68 (9)
C2—C1—C13—C7 −146.10 (10) C20—C32—C33—C34 76.01 (11)
C6—C1—C13—C14 −86.96 (12) C37—O6—C36—O7 −1.5 (2)
C2—C1—C13—C14 88.89 (12) C37—O6—C36—C35 176.50 (17)
C10—C11—C12—C7 0.93 (17) C36—O6—C37—C38 81.27 (17)
C8—C7—C12—C11 −2.00 (17) C37A—O6A—C36A—O7 3.5 (18)
C13—C7—C12—C11 179.57 (10) C37A—O6A—C36A—C35A 178.1 (14)
O3—C13—C14—C15 40.91 (12) C34—C35A—C36A—O7 95 (16)
C7—C13—C14—C15 162.82 (9) C34—C35A—C36A—O6A −79 (16)
C1—C13—C14—C15 −72.27 (11) C36A—O6A—C37A—C38A −83.3 (13)
C18—O2—C17—O1 −3.28 (17) C40—O5—C39—O4 −11.57 (16)
C18—O2—C17—C16 176.62 (10) C40—O5—C39—O3 168.94 (8)
C17—O2—C18—C19 −178.12 (10) C13—O3—C39—O4 2.35 (16)
C25—C20—C21—C22 1.80 (17) C13—O3—C39—O5 −178.17 (8)
C32—C20—C21—C22 −172.42 (10) C39—O5—C40—C41 −83.02 (12)
C20—C21—C22—C23 −0.77 (18) C43—O10—C42—O9 0.13 (16)
C21—C22—C23—C24 −0.87 (18) C43—O10—C42—O8 −179.54 (8)
C22—C23—C24—C25 1.46 (18) C32—O8—C42—O9 −6.90 (16)
C23—C24—C25—C20 −0.42 (18) C32—O8—C42—O10 172.76 (8)
C21—C20—C25—C24 −1.20 (17) C42—O10—C43—C44 160.11 (9)
C32—C20—C25—C24 172.96 (10)

Hydrogen-bond geometry (Å, º) 

D—H···A D—H H···A D···A D—H···A

C8—H8···O7 0.95 2.56 3.4079 (14) 149
C14—H14A···O7 0.99 2.61 3.4398 (14) 142
C18—H18A···O1i 0.99 2.62 3.4119 (15) 137



data reports

data-10IUCrData (2019). 4, x191526    

C31—H31···O1 0.95 2.43 3.3617 (15) 169
C33—H33B···O1 0.99 2.61 3.3008 (13) 127

Symmetry code: (i) −x+2, −y+1, −z+2.