organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoIUCrDATA
ISSN: 2414-3146

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

aEscuela de Quimica, Universidad de Costa Rica, 2060, San Pedro, San Jose, Costa Rica
*Correspondence e-mail: jorge.cabezas@ucr.ac.cr

Edited by W. T. A. Harrison, University of Aberdeen, Scotland (Received 4 October 2019; accepted 12 November 2019; online 15 November 2019)

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.

3D view (loading...)
[Scheme 3D1]
Chemical scheme
[Scheme 1]

Structure description

Highly functionalized homopropagyl alcohols are useful building blocks in organic synthesis (Kim et al., 2017[Kim, J., Jeong, W. & Rhee, Y. H. (2017). Org. Lett. 19, 242-245.]; Foley & Leighton, 2015[Foley, C. N. & Leighton, J. L. (2015). Org. Lett. 17, 5858-5861.]; Francais et al., 2010[Francais, A., Leyva, A., Etxebarria-Jardi, G. & Ley, S. V. (2010). Org. Lett. 12, 340-343.]; Hosseyni et al., 2016[Hosseyni, S., Wojtas, L., Li, M. & Shi, X. (2016). J. Am. Chem. Soc. 138, 3994-3997.]; Gao et al., 2014[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.]; Trost & Rhee 2003[Trost, B. M. & Rhee, Y. H. (2003). J. Am. Chem. Soc. 125, 7482-7483.]; Yadav & Maiti, 2002[Yadav, J. S. & Maiti, A. (2002). Tetrahedron, 58, 4955-4961.]). For instance, the title compound, where the homopropargyl alcohol is masked as a carbonate, might serve as an inter­mediate in the synthesis of α, β-unsaturated γ-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[link]. 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 inter­actions occur (Table 1[link], Fig. 2[link]).

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA 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+2, -y+1, -z+2.
[Figure 1]
Figure 1
The title mol­ecule with 50% probability ellipsoids. The minor disorder component for the C20 mol­ecule is not shown.
[Figure 2]
Figure 2
The crystal packing of the title compound.

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[Cabezas, J. A., Pereira, A. & Amey, A. (2001). Tetrahedron Lett. 42, 6819-6822.]) (Fig. 3[link]). The product was purified by column chromatography using hexane-ether mixtures, and then recrystallized from ethyl acetate solution.

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

Refinement

Crystal data, data collection and structure refinement are summarized in Table 2[link].

Table 2
Experimental details

Crystal data
Chemical formula C22H22O5
Mr 366.39
Crystal system, space group Triclinic, P[\overline{1}]
Temperature (K) 100
a, b, c (Å) 9.9461 (4), 12.1510 (5), 16.8171 (7)
α, β, γ (°) 105.006 (1), 94.220 (1), 104.926 (1)
V3) 1875.34 (13)
Z 4
Radiation type Mo Kα
μ (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[Bruker (2015). APEX3, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.])
Tmin, Tmax 0.721, 0.746
No. of measured, independent and observed [I > 2σ(I)] reflections 54801, 8599, 7059
Rint 0.028
(sin θ/λ)max−1) 0.650
 
Refinement
R[F2 > 2σ(F2)], wR(F2), 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
Δρmax, Δρmin (e Å−3) 0.36, −0.25
Computer programs: APEX3 and SAINT (Bruker, 2015[Bruker (2015). APEX3, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]), SHELXT2014/5 (Sheldrick, 2015a[Sheldrick, G. M. (2015a). Acta Cryst. A71, 3-8.]), SHELXL2018/3 (Sheldrick, 2015b[Sheldrick, G. M. (2015b). Acta Cryst. C71, 3-8.]), shelXle (Hübschle et al., 2011[Hübschle, C. B., Sheldrick, G. M. & Dittrich, B. (2011). J. Appl. Cryst. 44, 1281-1284.]), Mercury (Macrae et al., 2006[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.]) and publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).

Structural data


Computing details top

Data collection: APEX3 (Bruker, 2015); cell refinement: SAINT (Bruker, 2015); data reduction: SAINT (Bruker, 2015); program(s) used to solve structure: SHELXT2014/5 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2018/3 (Sheldrick, 2015b); molecular graphics: shelXle (Hübschle et al., 2011); software used to prepare material for publication: Mercury (Macrae et al., 2006) and publCIF (Westrip, 2010).

Ethyl 5-[(ethoxycarbonyl)oxy]-5,5-diphenylpent-2-ynoate top
Crystal data top
C22H22O5Z = 4
Mr = 366.39F(000) = 776
Triclinic, P1Dx = 1.298 Mg m3
a = 9.9461 (4) ÅMo Kα radiation, λ = 0.71073 Å
b = 12.1510 (5) ÅCell parameters from 9767 reflections
c = 16.8171 (7) Åθ = 2.8–27.5°
α = 105.006 (1)°µ = 0.09 mm1
β = 94.220 (1)°T = 100 K
γ = 104.926 (1)°Block, light yellow
V = 1875.34 (13) Å30.22 × 0.17 × 0.13 mm
Data collection top
Bruker D8 Venture
diffractometer
8599 independent reflections
Radiation source: Incoatec Microsource7059 reflections with I > 2σ(I)
Detector resolution: 10.4167 pixels mm-1Rint = 0.028
ω scansθmax = 27.5°, θmin = 2.6°
Absorption correction: multi-scan
(SADABS; Bruker, 2015)
h = 1212
Tmin = 0.721, Tmax = 0.746k = 1515
54801 measured reflectionsl = 2121
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.036Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.093H-atom parameters constrained
S = 1.02 w = 1/[σ2(Fo2) + (0.0454P)2 + 0.5843P]
where P = (Fo2 + 2Fc2)/3
8599 reflections(Δ/σ)max = 0.001
532 parametersΔρmax = 0.36 e Å3
186 restraintsΔρmin = 0.24 e Å3
Special details top

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.

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) top
xyzUiso*/UeqOcc. (<1)
O10.81699 (8)0.40080 (8)0.89228 (5)0.02350 (19)
C10.27160 (11)0.01485 (10)0.83753 (7)0.0148 (2)
O20.77716 (8)0.29149 (7)0.98210 (5)0.01976 (18)
C20.38374 (12)0.03498 (10)0.88071 (7)0.0189 (2)
H20.4364040.0236990.9297500.023*
O30.28485 (8)0.14591 (7)0.95391 (5)0.01491 (16)
C30.41879 (13)0.14048 (11)0.85231 (8)0.0231 (3)
H30.4947870.1539000.8823120.028*
O40.25585 (8)0.32945 (7)0.96811 (5)0.02070 (18)
C40.34348 (13)0.22619 (10)0.78046 (8)0.0234 (3)
H40.3682870.2979050.7609860.028*
O50.34124 (8)0.27211 (7)1.07449 (5)0.01890 (17)
C50.23196 (13)0.20709 (10)0.73711 (8)0.0222 (2)
H50.1800790.2657660.6878530.027*
C60.19596 (12)0.10203 (10)0.76568 (7)0.0184 (2)
H60.1189890.0895430.7359060.022*
C70.07917 (11)0.08796 (9)0.84860 (7)0.0144 (2)
C80.01672 (12)0.12322 (10)0.78644 (7)0.0178 (2)
H80.0727360.1590650.7514420.021*
O80.70969 (8)0.34032 (7)0.55046 (5)0.01559 (16)
C90.12827 (12)0.10579 (10)0.77571 (7)0.0202 (2)
H90.1707390.1297950.7331640.024*
O90.74620 (9)0.16970 (7)0.56704 (5)0.02059 (18)
C110.14925 (12)0.01679 (11)0.88751 (7)0.0210 (2)
H110.2055260.0197040.9221250.025*
C100.21110 (12)0.05387 (10)0.82637 (7)0.0204 (2)
H100.3096310.0436660.8193450.024*
O100.63254 (9)0.18044 (7)0.44917 (5)0.01925 (17)
C130.23688 (11)0.10354 (9)0.86421 (6)0.0138 (2)
C120.00532 (12)0.03314 (10)0.89790 (7)0.0184 (2)
H120.0363390.0065700.9392640.022*
C140.32186 (11)0.18946 (10)0.81982 (7)0.0153 (2)
H14A0.3100360.1478210.7596600.018*
H14B0.2834660.2582060.8258330.018*
C160.59229 (12)0.27350 (10)0.88425 (7)0.0174 (2)
C150.47165 (11)0.23273 (10)0.85321 (7)0.0160 (2)
C170.73983 (11)0.32921 (10)0.91892 (7)0.0167 (2)
C180.92621 (12)0.33846 (12)1.01716 (8)0.0260 (3)
H18A0.9523700.4261111.0399380.031*
H18B0.9849140.3180490.9737010.031*
C190.94828 (14)0.28291 (13)1.08508 (8)0.0295 (3)
H19A0.9177260.1961041.0622240.044*
H19B0.8932080.3070041.1289520.044*
H19C1.0483310.3093091.1084530.044*
C200.73795 (11)0.52715 (10)0.64707 (7)0.0153 (2)
C210.82971 (12)0.62948 (10)0.70272 (7)0.0190 (2)
H210.9152970.6258440.7294760.023*
C220.79681 (13)0.73670 (10)0.71929 (8)0.0228 (3)
H220.8594480.8058020.7578280.027*
C230.67345 (13)0.74343 (11)0.68001 (8)0.0230 (3)
H230.6506300.8166980.6920600.028*
C240.58307 (13)0.64285 (11)0.62293 (8)0.0232 (3)
H240.4992790.6477600.5949080.028*
C250.61448 (12)0.53500 (10)0.60654 (7)0.0190 (2)
H250.5518120.4663000.5676420.023*
C260.92255 (11)0.41887 (9)0.65338 (7)0.0163 (2)
C271.00433 (13)0.44168 (12)0.59285 (8)0.0259 (3)
H270.9611090.4456150.5417760.031*
C281.14856 (14)0.45879 (12)0.60613 (9)0.0319 (3)
H281.2034680.4740160.5641770.038*
C291.21224 (13)0.45368 (11)0.68038 (9)0.0291 (3)
H291.3109880.4655720.6896820.035*
C301.13185 (13)0.43123 (11)0.74099 (9)0.0267 (3)
H301.1756390.4275900.7920120.032*
C310.98712 (12)0.41386 (10)0.72797 (8)0.0217 (2)
H310.9325450.3985930.7700510.026*
C320.76597 (11)0.40682 (9)0.63736 (7)0.0141 (2)
C330.68114 (11)0.34551 (10)0.69605 (7)0.0150 (2)
H33A0.7190100.2806350.7038970.018*
H33B0.6929820.4041370.7511970.018*
C340.53171 (12)0.29679 (10)0.66250 (7)0.0158 (2)
O70.17896 (8)0.13603 (8)0.61612 (5)0.02321 (19)
O60.26944 (9)0.16917 (9)0.50205 (6)0.0206 (2)0.880 (2)
C350.4135 (2)0.2486 (3)0.62745 (19)0.0171 (5)0.880 (2)
C360.27374 (17)0.17945 (14)0.58293 (10)0.0169 (4)0.880 (2)
C370.13761 (18)0.09582 (16)0.44892 (11)0.0230 (4)0.880 (2)
H37A0.0994840.0250720.4680750.028*0.880 (2)
H37B0.1554900.0679320.3910250.028*0.880 (2)
C380.03124 (16)0.16443 (14)0.45078 (9)0.0276 (3)0.880 (2)
H38A0.0080230.1867840.5072620.041*0.880 (2)
H38B0.0541730.1148590.4120560.041*0.880 (2)
H38C0.0705390.2363710.4342220.041*0.880 (2)
O6A0.2498 (7)0.2460 (7)0.5284 (4)0.0205 (12)0.120 (2)
C35A0.4113 (15)0.266 (3)0.6382 (17)0.0171 (5)0.120 (2)
C36A0.2675 (13)0.2105 (12)0.5967 (8)0.0185 (14)0.120 (2)
C37A0.1103 (11)0.1935 (9)0.4795 (6)0.0259 (15)0.120 (2)
H37C0.0913240.2457200.4462390.031*0.120 (2)
H37D0.0384830.1855520.5170380.031*0.120 (2)
C38A0.1017 (16)0.0761 (13)0.4239 (9)0.031 (3)0.120 (2)
H38D0.1763410.0838220.3890050.046*0.120 (2)
H38E0.0098100.0430310.3883830.046*0.120 (2)
H38F0.1133970.0228960.4571840.046*0.120 (2)
C390.29032 (11)0.25774 (10)0.99560 (7)0.0157 (2)
C400.38139 (13)0.39366 (10)1.12861 (7)0.0221 (2)
H40A0.3788940.3930531.1872350.026*
H40B0.3136500.4350681.1141430.026*
C410.52676 (13)0.45870 (11)1.11907 (9)0.0285 (3)
H41A0.5262160.4679341.0628730.043*
H41B0.5920090.4133031.1279470.043*
H41C0.5569990.5373231.1601740.043*
C420.70128 (11)0.22392 (10)0.52654 (7)0.0156 (2)
C430.61129 (12)0.05383 (10)0.41182 (7)0.0196 (2)
H43A0.5874460.0099680.4533470.024*
H43B0.6979860.0397040.3913960.024*
C440.49251 (12)0.01266 (10)0.34075 (7)0.0209 (2)
H44A0.5160010.0587080.3011260.031*
H44B0.4065510.0243030.3620500.031*
H44C0.4774120.0719170.3126740.031*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0173 (4)0.0282 (5)0.0221 (4)0.0020 (3)0.0007 (3)0.0120 (4)
C10.0136 (5)0.0152 (5)0.0168 (5)0.0033 (4)0.0045 (4)0.0067 (4)
O20.0137 (4)0.0241 (4)0.0211 (4)0.0017 (3)0.0010 (3)0.0105 (3)
C20.0170 (5)0.0187 (6)0.0214 (6)0.0053 (4)0.0012 (4)0.0070 (5)
O30.0157 (4)0.0148 (4)0.0131 (4)0.0039 (3)0.0009 (3)0.0034 (3)
C30.0209 (6)0.0223 (6)0.0310 (7)0.0097 (5)0.0046 (5)0.0122 (5)
O40.0212 (4)0.0190 (4)0.0229 (4)0.0081 (3)0.0009 (3)0.0060 (3)
C40.0248 (6)0.0158 (6)0.0325 (7)0.0077 (5)0.0114 (5)0.0084 (5)
O50.0208 (4)0.0172 (4)0.0155 (4)0.0038 (3)0.0017 (3)0.0019 (3)
C50.0224 (6)0.0175 (6)0.0226 (6)0.0018 (5)0.0054 (5)0.0023 (5)
C60.0159 (5)0.0192 (6)0.0188 (6)0.0031 (4)0.0020 (4)0.0053 (5)
C70.0123 (5)0.0131 (5)0.0159 (5)0.0029 (4)0.0010 (4)0.0020 (4)
C80.0152 (5)0.0183 (5)0.0202 (6)0.0035 (4)0.0014 (4)0.0075 (5)
O80.0189 (4)0.0138 (4)0.0133 (4)0.0048 (3)0.0007 (3)0.0029 (3)
C90.0173 (6)0.0191 (6)0.0232 (6)0.0062 (4)0.0028 (4)0.0053 (5)
O90.0237 (4)0.0195 (4)0.0203 (4)0.0101 (3)0.0006 (3)0.0056 (3)
C110.0167 (6)0.0226 (6)0.0209 (6)0.0017 (5)0.0055 (4)0.0049 (5)
C100.0119 (5)0.0190 (6)0.0254 (6)0.0038 (4)0.0006 (4)0.0007 (5)
O100.0259 (4)0.0146 (4)0.0159 (4)0.0070 (3)0.0010 (3)0.0021 (3)
C130.0127 (5)0.0151 (5)0.0126 (5)0.0027 (4)0.0002 (4)0.0044 (4)
C120.0172 (5)0.0208 (6)0.0165 (5)0.0038 (4)0.0011 (4)0.0060 (4)
C140.0125 (5)0.0173 (5)0.0167 (5)0.0026 (4)0.0008 (4)0.0077 (4)
C160.0173 (6)0.0176 (5)0.0184 (5)0.0042 (4)0.0029 (4)0.0077 (4)
C150.0164 (6)0.0156 (5)0.0168 (5)0.0041 (4)0.0032 (4)0.0064 (4)
C170.0152 (5)0.0178 (5)0.0161 (5)0.0039 (4)0.0013 (4)0.0041 (4)
C180.0128 (6)0.0373 (7)0.0255 (6)0.0000 (5)0.0031 (5)0.0139 (6)
C190.0224 (6)0.0400 (8)0.0258 (7)0.0054 (6)0.0029 (5)0.0144 (6)
C200.0164 (5)0.0156 (5)0.0153 (5)0.0050 (4)0.0042 (4)0.0058 (4)
C210.0172 (5)0.0185 (6)0.0202 (6)0.0042 (4)0.0019 (4)0.0049 (5)
C220.0243 (6)0.0153 (6)0.0256 (6)0.0026 (5)0.0051 (5)0.0033 (5)
C230.0281 (6)0.0167 (6)0.0289 (6)0.0101 (5)0.0094 (5)0.0091 (5)
C240.0234 (6)0.0242 (6)0.0266 (6)0.0115 (5)0.0026 (5)0.0106 (5)
C250.0196 (6)0.0173 (5)0.0191 (6)0.0049 (4)0.0001 (4)0.0050 (4)
C260.0143 (5)0.0121 (5)0.0216 (6)0.0039 (4)0.0020 (4)0.0033 (4)
C270.0203 (6)0.0305 (7)0.0258 (6)0.0042 (5)0.0050 (5)0.0089 (5)
C280.0201 (6)0.0345 (7)0.0376 (8)0.0037 (5)0.0124 (5)0.0063 (6)
C290.0137 (6)0.0211 (6)0.0471 (8)0.0046 (5)0.0026 (5)0.0017 (6)
C300.0181 (6)0.0227 (6)0.0369 (7)0.0045 (5)0.0049 (5)0.0085 (5)
C310.0172 (6)0.0205 (6)0.0270 (6)0.0037 (5)0.0010 (5)0.0086 (5)
C320.0135 (5)0.0141 (5)0.0133 (5)0.0027 (4)0.0001 (4)0.0032 (4)
C330.0137 (5)0.0162 (5)0.0152 (5)0.0040 (4)0.0011 (4)0.0051 (4)
C340.0176 (5)0.0158 (5)0.0168 (5)0.0065 (4)0.0045 (4)0.0072 (4)
O70.0169 (4)0.0292 (5)0.0237 (4)0.0031 (3)0.0045 (3)0.0111 (4)
O60.0144 (4)0.0276 (6)0.0172 (5)0.0016 (4)0.0014 (3)0.0067 (4)
C350.0172 (6)0.0184 (12)0.0182 (11)0.0069 (5)0.0042 (5)0.0074 (8)
C360.0145 (6)0.0179 (8)0.0198 (8)0.0068 (6)0.0024 (5)0.0059 (6)
C370.0173 (9)0.0275 (9)0.0179 (9)0.0005 (7)0.0004 (6)0.0027 (7)
C380.0198 (8)0.0376 (9)0.0235 (7)0.0063 (6)0.0009 (6)0.0084 (6)
O6A0.0176 (19)0.023 (2)0.0191 (19)0.0049 (18)0.0009 (17)0.0056 (17)
C35A0.0172 (6)0.0184 (12)0.0182 (11)0.0069 (5)0.0042 (5)0.0074 (8)
C36A0.018 (2)0.021 (2)0.018 (2)0.007 (2)0.002 (2)0.008 (2)
C37A0.019 (2)0.032 (2)0.022 (2)0.003 (2)0.003 (2)0.006 (2)
C38A0.023 (4)0.037 (4)0.021 (4)0.002 (4)0.002 (4)0.002 (4)
C390.0111 (5)0.0167 (5)0.0177 (5)0.0023 (4)0.0023 (4)0.0039 (4)
C400.0255 (6)0.0176 (6)0.0179 (6)0.0051 (5)0.0007 (5)0.0016 (5)
C410.0249 (6)0.0213 (6)0.0349 (7)0.0014 (5)0.0050 (5)0.0086 (5)
C420.0143 (5)0.0163 (5)0.0165 (5)0.0049 (4)0.0041 (4)0.0039 (4)
C430.0249 (6)0.0144 (5)0.0188 (6)0.0077 (5)0.0020 (5)0.0019 (4)
C440.0224 (6)0.0157 (6)0.0219 (6)0.0037 (5)0.0006 (5)0.0032 (5)
Geometric parameters (Å, º) top
O1—C171.2062 (14)C23—C241.3866 (18)
C1—C61.3933 (16)C23—H230.9500
C1—C21.3943 (15)C24—C251.3883 (16)
C1—C131.5279 (15)C24—H240.9500
O2—C171.3261 (13)C25—H250.9500
O2—C181.4603 (14)C26—C271.3879 (17)
C2—C31.3895 (16)C26—C311.3896 (16)
C2—H20.9500C26—C321.5230 (15)
O3—C391.3431 (13)C27—C281.3878 (18)
O3—C131.4608 (13)C27—H270.9500
C3—C41.3852 (18)C28—C291.381 (2)
C3—H30.9500C28—H280.9500
O4—C391.1957 (13)C29—C301.380 (2)
C4—C51.3845 (18)C29—H290.9500
C4—H40.9500C30—C311.3921 (16)
O5—C391.3353 (13)C30—H300.9500
O5—C401.4545 (13)C31—H310.9500
C5—C61.3899 (16)C32—C331.5558 (15)
C5—H50.9500C33—C341.4588 (15)
C6—H60.9500C33—H33A0.9900
C7—C81.3912 (15)C33—H33B0.9900
C7—C121.3919 (15)C34—C35A1.166 (13)
C7—C131.5251 (14)C34—C351.199 (2)
C8—C91.3934 (16)O7—C361.2052 (18)
C8—H80.9500O7—C36A1.219 (12)
O8—C421.3450 (13)O6—C361.3297 (18)
O8—C321.4620 (13)O6—C371.4577 (18)
C9—C101.3843 (17)C35—C361.455 (2)
C9—H90.9500C37—C381.504 (2)
O9—C421.1986 (14)C37—H37A0.9900
C11—C121.3850 (16)C37—H37B0.9900
C11—C101.3887 (17)C38—H38A0.9800
C11—H110.9500C38—H38B0.9800
C10—H100.9500C38—H38C0.9800
O10—C421.3292 (13)O6A—C36A1.343 (12)
O10—C431.4556 (13)O6A—C37A1.453 (11)
C13—C141.5504 (14)C35A—C36A1.448 (14)
C12—H120.9500C37A—C38A1.468 (14)
C14—C151.4601 (15)C37A—H37C0.9900
C14—H14A0.9900C37A—H37D0.9900
C14—H14B0.9900C38A—H38D0.9800
C16—C151.1939 (16)C38A—H38E0.9800
C16—C171.4524 (15)C38A—H38F0.9800
C18—C191.4989 (17)C40—C411.5006 (18)
C18—H18A0.9900C40—H40A0.9900
C18—H18B0.9900C40—H40B0.9900
C19—H19A0.9800C41—H41A0.9800
C19—H19B0.9800C41—H41B0.9800
C19—H19C0.9800C41—H41C0.9800
C20—C211.3935 (16)C43—C441.5008 (16)
C20—C251.3973 (15)C43—H43A0.9900
C20—C321.5281 (15)C43—H43B0.9900
C21—C221.3882 (16)C44—H44A0.9800
C21—H210.9500C44—H44B0.9800
C22—C231.3817 (18)C44—H44C0.9800
C22—H220.9500
C6—C1—C2118.89 (10)C28—C27—H27119.6
C6—C1—C13119.69 (10)C26—C27—H27119.6
C2—C1—C13121.30 (10)C29—C28—C27119.97 (12)
C17—O2—C18114.95 (9)C29—C28—H28120.0
C3—C2—C1120.29 (11)C27—C28—H28120.0
C3—C2—H2119.9C30—C29—C28119.74 (12)
C1—C2—H2119.9C30—C29—H29120.1
C39—O3—C13119.10 (8)C28—C29—H29120.1
C4—C3—C2120.33 (11)C29—C30—C31120.54 (12)
C4—C3—H3119.8C29—C30—H30119.7
C2—C3—H3119.8C31—C30—H30119.7
C5—C4—C3119.85 (11)C26—C31—C30119.95 (12)
C5—C4—H4120.1C26—C31—H31120.0
C3—C4—H4120.1C30—C31—H31120.0
C39—O5—C40115.48 (9)O8—C32—C26109.63 (8)
C4—C5—C6119.97 (11)O8—C32—C20104.17 (8)
C4—C5—H5120.0C26—C32—C20112.04 (9)
C6—C5—H5120.0O8—C32—C33109.97 (8)
C5—C6—C1120.67 (11)C26—C32—C33112.54 (9)
C5—C6—H6119.7C20—C32—C33108.15 (9)
C1—C6—H6119.7C34—C33—C32111.71 (9)
C8—C7—C12119.15 (10)C34—C33—H33A109.3
C8—C7—C13123.00 (10)C32—C33—H33A109.3
C12—C7—C13117.84 (9)C34—C33—H33B109.3
C7—C8—C9119.76 (11)C32—C33—H33B109.3
C7—C8—H8120.1H33A—C33—H33B107.9
C9—C8—H8120.1C35A—C34—C33175.3 (14)
C42—O8—C32117.61 (8)C35—C34—C33172.53 (16)
C10—C9—C8120.72 (11)C36—O6—C37116.13 (12)
C10—C9—H9119.6C34—C35—C36174.5 (3)
C8—C9—H9119.6O7—C36—O6126.34 (14)
C12—C11—C10119.83 (11)O7—C36—C35123.46 (19)
C12—C11—H11120.1O6—C36—C35110.17 (18)
C10—C11—H11120.1O6—C37—C38111.08 (14)
C9—C10—C11119.58 (10)O6—C37—H37A109.4
C9—C10—H10120.2C38—C37—H37A109.4
C11—C10—H10120.2O6—C37—H37B109.4
C42—O10—C43115.04 (9)C38—C37—H37B109.4
O3—C13—C7108.81 (8)H37A—C37—H37B108.0
O3—C13—C1103.54 (8)C37—C38—H38A109.5
C7—C13—C1112.21 (9)C37—C38—H38B109.5
O3—C13—C14110.73 (8)H38A—C38—H38B109.5
C7—C13—C14112.37 (9)C37—C38—H38C109.5
C1—C13—C14108.83 (9)H38A—C38—H38C109.5
C11—C12—C7120.93 (11)H38B—C38—H38C109.5
C11—C12—H12119.5C36A—O6A—C37A114.6 (8)
C7—C12—H12119.5C34—C35A—C36A170 (2)
C15—C14—C13112.62 (9)O7—C36A—O6A124.6 (10)
C15—C14—H14A109.1O7—C36A—C35A125.9 (15)
C13—C14—H14A109.1O6A—C36A—C35A109.3 (15)
C15—C14—H14B109.1O6A—C37A—C38A109.6 (10)
C13—C14—H14B109.1O6A—C37A—H37C109.8
H14A—C14—H14B107.8C38A—C37A—H37C109.8
C15—C16—C17176.04 (12)O6A—C37A—H37D109.8
C16—C15—C14175.92 (12)C38A—C37A—H37D109.8
O1—C17—O2125.22 (10)H37C—C37A—H37D108.2
O1—C17—C16122.99 (10)C37A—C38A—H38D109.5
O2—C17—C16111.78 (9)C37A—C38A—H38E109.5
O2—C18—C19106.98 (10)H38D—C38A—H38E109.5
O2—C18—H18A110.3C37A—C38A—H38F109.5
C19—C18—H18A110.3H38D—C38A—H38F109.5
O2—C18—H18B110.3H38E—C38A—H38F109.5
C19—C18—H18B110.3O4—C39—O5127.00 (10)
H18A—C18—H18B108.6O4—C39—O3127.29 (10)
C18—C19—H19A109.5O5—C39—O3105.70 (9)
C18—C19—H19B109.5O5—C40—C41110.11 (10)
H19A—C19—H19B109.5O5—C40—H40A109.6
C18—C19—H19C109.5C41—C40—H40A109.6
H19A—C19—H19C109.5O5—C40—H40B109.6
H19B—C19—H19C109.5C41—C40—H40B109.6
C21—C20—C25118.95 (10)H40A—C40—H40B108.2
C21—C20—C32119.96 (10)C40—C41—H41A109.5
C25—C20—C32120.84 (10)C40—C41—H41B109.5
C22—C21—C20120.41 (11)H41A—C41—H41B109.5
C22—C21—H21119.8C40—C41—H41C109.5
C20—C21—H21119.8H41A—C41—H41C109.5
C23—C22—C21120.34 (11)H41B—C41—H41C109.5
C23—C22—H22119.8O9—C42—O10126.63 (10)
C21—C22—H22119.8O9—C42—O8126.88 (10)
C22—C23—C24119.75 (11)O10—C42—O8106.49 (9)
C22—C23—H23120.1O10—C43—C44107.14 (9)
C24—C23—H23120.1O10—C43—H43A110.3
C23—C24—C25120.30 (11)C44—C43—H43A110.3
C23—C24—H24119.9O10—C43—H43B110.3
C25—C24—H24119.9C44—C43—H43B110.3
C24—C25—C20120.23 (11)H43A—C43—H43B108.5
C24—C25—H25119.9C43—C44—H44A109.5
C20—C25—H25119.9C43—C44—H44B109.5
C27—C26—C31119.08 (11)H44A—C44—H44B109.5
C27—C26—C32118.58 (10)C43—C44—H44C109.5
C31—C26—C32122.26 (10)H44A—C44—H44C109.5
C28—C27—C26120.73 (12)H44B—C44—H44C109.5
C6—C1—C2—C30.11 (17)C31—C26—C27—C280.28 (18)
C13—C1—C2—C3175.99 (10)C32—C26—C27—C28177.03 (11)
C1—C2—C3—C40.57 (18)C26—C27—C28—C290.3 (2)
C2—C3—C4—C50.55 (18)C27—C28—C29—C300.2 (2)
C3—C4—C5—C60.07 (18)C28—C29—C30—C310.10 (19)
C4—C5—C6—C10.39 (17)C27—C26—C31—C300.21 (17)
C2—C1—C6—C50.37 (17)C32—C26—C31—C30176.84 (10)
C13—C1—C6—C5175.58 (10)C29—C30—C31—C260.12 (18)
C12—C7—C8—C91.47 (17)C42—O8—C32—C2669.26 (11)
C13—C7—C8—C9179.81 (10)C42—O8—C32—C20170.67 (8)
C7—C8—C9—C100.12 (17)C42—O8—C32—C3354.98 (11)
C8—C9—C10—C111.20 (18)C27—C26—C32—O840.24 (13)
C12—C11—C10—C90.68 (17)C31—C26—C32—O8143.12 (10)
C39—O3—C13—C770.88 (11)C27—C26—C32—C2074.91 (13)
C39—O3—C13—C1169.59 (8)C31—C26—C32—C20101.74 (12)
C39—O3—C13—C1453.10 (12)C27—C26—C32—C33162.96 (10)
C8—C7—C13—O3137.44 (10)C31—C26—C32—C3320.40 (14)
C12—C7—C13—O344.20 (12)C21—C20—C32—O8148.68 (10)
C8—C7—C13—C1108.59 (12)C25—C20—C32—O837.21 (13)
C12—C7—C13—C169.77 (12)C21—C20—C32—C2630.25 (14)
C8—C7—C13—C1414.44 (15)C25—C20—C32—C26155.64 (10)
C12—C7—C13—C14167.19 (10)C21—C20—C32—C3394.36 (11)
C6—C1—C13—O3155.22 (9)C25—C20—C32—C3379.75 (12)
C2—C1—C13—O328.94 (13)O8—C32—C33—C3437.14 (12)
C6—C1—C13—C738.05 (13)C26—C32—C33—C34159.68 (9)
C2—C1—C13—C7146.10 (10)C20—C32—C33—C3476.01 (11)
C6—C1—C13—C1486.96 (12)C37—O6—C36—O71.5 (2)
C2—C1—C13—C1488.89 (12)C37—O6—C36—C35176.50 (17)
C10—C11—C12—C70.93 (17)C36—O6—C37—C3881.27 (17)
C8—C7—C12—C112.00 (17)C37A—O6A—C36A—O73.5 (18)
C13—C7—C12—C11179.57 (10)C37A—O6A—C36A—C35A178.1 (14)
O3—C13—C14—C1540.91 (12)C34—C35A—C36A—O795 (16)
C7—C13—C14—C15162.82 (9)C34—C35A—C36A—O6A79 (16)
C1—C13—C14—C1572.27 (11)C36A—O6A—C37A—C38A83.3 (13)
C18—O2—C17—O13.28 (17)C40—O5—C39—O411.57 (16)
C18—O2—C17—C16176.62 (10)C40—O5—C39—O3168.94 (8)
C17—O2—C18—C19178.12 (10)C13—O3—C39—O42.35 (16)
C25—C20—C21—C221.80 (17)C13—O3—C39—O5178.17 (8)
C32—C20—C21—C22172.42 (10)C39—O5—C40—C4183.02 (12)
C20—C21—C22—C230.77 (18)C43—O10—C42—O90.13 (16)
C21—C22—C23—C240.87 (18)C43—O10—C42—O8179.54 (8)
C22—C23—C24—C251.46 (18)C32—O8—C42—O96.90 (16)
C23—C24—C25—C200.42 (18)C32—O8—C42—O10172.76 (8)
C21—C20—C25—C241.20 (17)C42—O10—C43—C44160.11 (9)
C32—C20—C25—C24172.96 (10)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C8—H8···O70.952.563.4079 (14)149
C14—H14A···O70.992.613.4398 (14)142
C18—H18A···O1i0.992.623.4119 (15)137
C31—H31···O10.952.433.3617 (15)169
C33—H33B···O10.992.613.3008 (13)127
Symmetry code: (i) x+2, y+1, z+2.
 

Acknowledgements

We thank Dr Vojtech Jancik for crystallographic assistance.

Funding information

We acknowledge the Vicerrectoría de Investigación (UCR) for financial support

References

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