In the title compound, the ring conformations of the tetracycle are twist, chair, half-chair and chair–boat forms. In the crystal, intermolecular C—H⋯O and C—H⋯π interactions link molecules to construct a three-dimensional architecture.
Keywords: crystal structure, hydrogen bonds, taxane skeleton, paclitaxel, hydrogen bonding, C—H⋯π interactions
Abstract
In the title compound, C36H42O8, the dioxolane ring adopts a twist conformation; the two adjacent C atoms deviate alternately from the mean plane of other atoms by −0.287 (5) and 0.174 (5) Å. The cyclohexane, cyclohexadiene and central cyclooctane rings show chair, half-chair and boat–chair forms, respectively. As a result of the strained ring system, the tetrasubsituted olefin in the cyclohexadiene is skewed from an ideal planar structure. In the crystal, C—H⋯O hydrogen bonds connect the molecules into a sheet parallel to (100). The sheets are further linked by other weak C—H⋯O and C—H⋯π interactions, forming a three-dimensional network.
Chemical context
Paclitaxel is a well-known natural diterpenoid containing a taxane framework (tricyclo[9.3.1.03,8]pentadecane; Fig. 1 ▸), with a potent antitumor activity (Wall & Wani, 1995 ▸). The complicated structure and significant bioactivity have attracted chemical and medicinal interest. Previously, we have reported the crystal structures of the precursor for cyclization to build the taxane skeleton (Oishi, Yamaguchi et al., 2015 ▸), and cyclized compounds (Oishi, Fukaya et al., 2015 ▸) obtained in the synthetic study of paclitaxel. The title compound was afforded by further manipulation of functional groups of the cyclized compounds (Fukaya et al., 2015 ▸).
Figure 1.
Left: Structure of the tricyclo[9.3.1.03,8]pentadecane (taxane) skeleton; Right: The title compound, indicating the taxane skeleton with red lines. R 1 = OC(=O)Ph, R 2 = OCH2OCH3, R 3 = OCH2Ph.
Structural commentary
The molecular structure of the title compound is shown in Fig. 2 ▸. The dioxolane ring (C1/C2/O20/C21/O22) adopts a twist form with puckering parameters of Q(2) = 0.272 (2) Å and ϕ(2) = 58.3 (5)°. Atoms C1 and C2 deviate from the mean plane of the other atoms by −0.287 (5) and 0.174 (5) Å, respectively. The cyclohexane ring (C3–C8) adopts a chair form with puckering parameters of Q = 0.590 (2) Å, θ = 10.97 (19)°, ϕ = 294.8 (12)°, Q(2) = 0.110 (2) Å and Q(3) = 0.579 (2) Å. The large substituents (C3—C2, C7—O24 and C8—C9) are in equatorial positions, while the methoxymethoxy group (C4–O41) is slightly tilted from the ideal equatorial position with an angle to the Cremer & Pople plane of 59.01 (14)°.
Figure 2.
The molecular structure of the title compound with the atom labeling. Displacement ellipsoids are drawn at the 30% probability level. The purple dotted line indicates the intramolecular short contact. For clarity, only the H atoms attached to the chiral C atoms and related to the short contact are shown.
The cyclohexadiene ring (C1/C14/C13/C12/C11/C15) adopts a half-boat form with puckering parameters of Q = 0.598 (2) Å, θ = 115.68 (19)°, ϕ = 131.4 (3)°, Q(2) = 0.539 (2)° and Q(3) = 0.259 (2)°. The tetrasubstituted olefin (C10/C15/C11=C12/C13/C18) is skewed from an ideal planar structure as a result of the strain in the fused-ring system, the C10—C11=C12—C18, C15—C11=C12—C13, C10—C11=C12—C13 and C15—C11=C12—C18 torsion angles being −19.5 (3), −18.4 (3), 150.34 (18) and 171.80 (18)°, respectively. The dihedral angle between the C10/C11/C15 and C18/C12/C13 planes is 26.4 (3)°. The other olefin (C12/C13=C14/C1) slightly deviates from planarity with a C12—C13=C14—C1 torsion angle of 9.1 (3)°. The diene moiety shows a C11=C12—C13=C14 torsion angle of −17.7 (3)°. The central cyclooctane ring (C1–C3/C8–C11/C15) adopts a boat-chair form with puckering parameters of Q = 1.182 (2) Å, Q(2) = 0.897 (2) Å, ϕ(2) = 179.75 (15)°, Q(3) = 0.627 (2) Å, ϕ(3) = 2.7 (2)° and Q(4) = 0.441 (2) Å. There is an intramolecular short contact of 1.98 Å between atoms H2 and H9B (Fig. 2 ▸).
Supramolecular features
Intermolecular C—H⋯O interactions (C34—H34A⋯O43i and C38—H38⋯O23ii; Table 1 ▸ and Fig. 3 ▸) lead to the formation of a sheet parallel to (100). These sheets are further linked through weak intermolecular C—H⋯O and C—H⋯π interactions (C31—H31⋯O33iii, C2—H2⋯O23iv, C16—H16A⋯O23iv, C19—H19C⋯O23iv and C18—H18C⋯Cg v; Table 1 ▸, Figs. 4 ▸ and 5 ▸) into a three-dimensional network.
Table 1. Hydrogen-bond geometry (, ).
Cg is the centroid of the C35C40 benzene ring.
| DHA | DH | HA | D A | DHA |
|---|---|---|---|---|
| C34H34AO43i | 0.99 | 2.42 | 3.377(3) | 163 |
| C38H38O23ii | 0.95 | 2.44 | 3.295(3) | 149 |
| C31H31O33iii | 0.95 | 2.49 | 3.426(3) | 168 |
| C2H2O23iv | 1.00 | 2.51 | 3.433(3) | 153 |
| C16H16AO23iv | 0.98 | 2.53 | 3.357(3) | 142 |
| C19H19CO23iv | 0.98 | 2.54 | 3.477(3) | 160 |
| C18H18C Cg v | 0.98 | 2.89 | 3.492(3) | 121 |
Symmetry codes: (i) 
; (ii) 
; (iii) 
; (iv) 
; (v) 
.
Figure 3.
A partial packing view showing a sheet parallel to (100). Black dashed lines indicate the intermolecular C—H⋯O interactions. Only H atoms involved in hydrogen bonds are shown for clarity. [Symmetry codes: (i) x, y + 1, z; (ii) x, y + 1, z − 1.]
Figure 4.
A packing diagram showing the connections between enantiomers. Black dashed lines indicate the intermolecular C—H⋯O interactions. Only H atoms involved in hydrogen bonds are shown for clarity. [Symmetry codes: (ii) x, y + 1, z − 1; (iii) −x + 1, −y + 1, −z + 1; (iv) −x + 1, −y, −z + 2.]
Figure 5.
A packing diagram viewed down the c axis. Black dashed lines indicate the intermolecular C—H⋯O and C—H⋯π interactions. Cg is the centroid of the C35–C40 benzene ring. Only H atoms involved in hydrogen bonds are shown for clarity. [Symmetry codes: (iii) −x + 1, −y + 1, −z + 1; (v) −x, −y + 1, −z + 1.]
Database survey
In the Cambridge Structural Database (CSD, Version 5.36, November 2014; Groom & Allen, 2014 ▸), 85 structures containing a tricyclo[9.3.1.03,8]pentadec-11-ene skeleton, (a), are registered (Fig. 6 ▸). These include a large number of paclitaxels and its analogues, and one compound (NEGBOQ; Poujol et al., 1997 ▸) containing a 2,4-dioxatetracyclo[12.3.1.01,5.06,11]octadec-14-ene skeleton, (e), which is a dihydro derivative for the tetracyclic core of the title compound, (d). Another related structure (SOJWOD; Paquette & Zhao, 1998 ▸) containing a tricyclo[9.3.1.03,8]pentadec-13-ene skeleton, (b), has also been reported.
Figure 6.
Core structures for database survey; tricyclo[9.3.1.03,8]pentadecane (taxane) and its (a) 11-ene and (b) 13-ene derivatives, (c) bicyclo[5.3.1]undeca-7,9-diene, (d) the tetracyclic core of the title compound with ring labelling and (e) its dihydro derivative and (f) the regioisomer of olefin. The ring-fusion geometries are similar to the title compound in each of the related structures, as cis-AB, trans-BC and trans-BD.
On the other hand, there are two related structures (GOQBET and GOQBIX; Keil et al., 1994 ▸) containing a bicyclo[5.3.1]undeca-7,9-diene skeleton, (c). Additionally, related tetracyclic taxoid (ILIQUP; Ohba et al., 2003 ▸) and cyclic precursors for a taxane framework (NOTROF; Oishi, Yamaguchi et al., 2015 ▸) were obtained in our previous study. Furthermore, the structures of the three related tetracyclic compounds have been reported (Oishi, Fukaya et al., 2015 ▸). There are other crystalline compounds, closely related to the title compound with 2,4-dioxatetracyclo[12.3.1.01,5.06,11]octadeca-8,14-diene skeleton, (f) (Nicolaou, Ueno et al., 1995 ▸; Nicolaou, Yang et al., 1995 ▸), but they have not been deposited in the CSD.
Synthesis and crystallization
The title compound was provided in a synthetic study on paclitaxel (Fukaya et al., 2015 ▸). The cyclohexadiene unit (C1/C14/C13/C12/C11/C15) was synthesized according to the reported procedure (Nicolaou, Liu et al., 1995 ▸), and coupled with the substituted cyclohexane unit (C3–C8) prepared from 3-methylanisole by a Shapiro reaction (Nicolaou, Liu et al., 1995 ▸). A cyclization reaction followed by further manipulations of the functional groups afforded the title compound. Purification was carried out by silica gel chromatography, and colorless crystals were obtained from a benzene solution under a pentane-saturated atmosphere by slow evaporation at ambient temperature.
Refinement
Crystal data, data collection and structure refinement details are summarized in Table 2 ▸. C-bound H atoms were positioned geometrically with C—H = 0.95–1.00 Å, and constrained to ride on their parent atoms with U iso(H) = 1.2U eq(C) or 1.5U eq(methyl C).
Table 2. Experimental details.
| Crystal data | |
| Chemical formula | C36H42O8 |
| M r | 602.69 |
| Crystal system, space group | Triclinic, P
|
| Temperature (K) | 90 |
| a, b, c () | 10.9358(6), 11.6121(6), 13.6833(7) |
| , , () | 72.148(2), 86.447(2), 66.766(2) |
| V (3) | 1516.36(14) |
| Z | 2 |
| Radiation type | Mo K |
| (mm1) | 0.09 |
| Crystal size (mm) | 0.32 0.27 0.16 |
| Data collection | |
| Diffractometer | Bruker D8 Venture |
| Absorption correction | Multi-scan (SADABS; Bruker, 2014 ▸) |
| T min, T max | 0.97, 0.98 |
| No. of measured, independent and observed [I > 2(I)] reflections | 27885, 5346, 4078 |
| R int | 0.052 |
| (sin /)max (1) | 0.595 |
| Refinement | |
| R[F 2 > 2(F 2)], wR(F 2), S | 0.047, 0.120, 1.04 |
| No. of reflections | 5346 |
| No. of parameters | 402 |
| H-atom treatment | H-atom parameters constrained |
| max, min (e 3) | 0.59, 0.23 |
Supplementary Material
Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S2056989015007136/is5396sup1.cif
Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015007136/is5396Isup2.hkl
CCDC reference: 1058739
Additional supporting information: crystallographic information; 3D view; checkCIF report
Acknowledgments
This research was partially supported by the Keio Gijuku Fukuzawa Memorial Fund for the Advancement of Education and Research. We thank Professor T. Noda (Kanagawa Institute of Technology, Japan) for providing a mass spectrometry apparatus for our use. We also thank Professor S. Ohba (Keio University, Japan) for his valuable advice.
supplementary crystallographic information
Crystal data
| C36H42O8 | F(000) = 644 |
| Mr = 602.69 | Dx = 1.320 Mg m−3 |
| Triclinic, P1 | Melting point: 465.2 K |
| a = 10.9358 (6) Å | Mo Kα radiation, λ = 0.71073 Å |
| b = 11.6121 (6) Å | Cell parameters from 9212 reflections |
| c = 13.6833 (7) Å | θ = 2.2–25.0° |
| α = 72.148 (2)° | µ = 0.09 mm−1 |
| β = 86.447 (2)° | T = 90 K |
| γ = 66.766 (2)° | Prism, colorless |
| V = 1516.36 (14) Å3 | 0.32 × 0.27 × 0.16 mm |
| Z = 2 |
Data collection
| Bruker D8 Venture diffractometer | 5346 independent reflections |
| Radiation source: fine-focus sealed tube | 4078 reflections with I > 2σ(I) |
| Multilayered confocal mirror monochromator | Rint = 0.052 |
| Detector resolution: 8.333 pixels mm-1 | θmax = 25.0°, θmin = 2.1° |
| φ and ω scans | h = −13→13 |
| Absorption correction: multi-scan (SADABS; Bruker, 2014) | k = −13→13 |
| Tmin = 0.97, Tmax = 0.98 | l = −16→16 |
| 27885 measured reflections |
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)] = 0.047 | Hydrogen site location: inferred from neighbouring sites |
| wR(F2) = 0.120 | H-atom parameters constrained |
| S = 1.04 | w = 1/[σ2(Fo2) + (0.0504P)2 + 1.0416P] where P = (Fo2 + 2Fc2)/3 |
| 5346 reflections | (Δ/σ)max = 0.001 |
| 402 parameters | Δρmax = 0.59 e Å−3 |
| 0 restraints | Δρmin = −0.23 e Å−3 |
Special details
| Experimental. M.p. 462.2–465.2 K (not corrected); IR (film): 2940, 1806, 1716, 1274, 1109, 1043, 713 cm-1; 1H NMR (500 MHz, CDCl3): δ (p.p.m.) 8.03 (dd, J = 8.3, 1.2 Hz, 2H), 7.61 (tt, J = 7.5, 1.2 Hz, 1H), 7.49 (ddd, J = 8.3, 7.5, 1.7 Hz, 2H), 7.23–7.12 (m, 5H), 6.17 (d, J = 9.2 Hz, 1H), 5.63 (d, J = 9.2 Hz, 1H), 4.94 (d, J = 4.9 Hz, 1H), 4.90 (dd, J = 11.3, 5.2 Hz, 1H), 4.75 (d, J = 6.9 Hz, 1H), 4.65 (dd, J = 11.7, 5.4 Hz, 1H), 4.50 (d, J = 6.9 Hz, 1H), 4.47 (d, J = 12.0 Hz, 1H), 4.24 (d, J = 12.0 Hz, 1H), 3.70 (ddd, J = 10.5, 10.5, 4.9 Hz, 1H), 3.33 (s, 3H), 2.26 (dddd, J = 13.4, 5.0, 4.9, 2.6 Hz, 1H), 2.12 (dd, J = 15.9, 5.4 Hz, 1H), 2.04 (dd, J = 10.5, 4.9 Hz, 1H), 1.99 (dd, J = 15.9, 11.7 Hz, 1H), 1.91–1.85 (m, 1H), 1.84–1.73 (m, 1H), 1.80 (s, 3H), 1.58 (s, 3H), 1.50 (s, 3H), 1.35–1.24 (m, 1H), 1.18 (s, 3H); 13C NMR (125 MHz, CDCl3): δ (p.p.m.) 165.9 (C), 154.6 (C), 138.3 (C), 138.2 (C), 137.8 (C), 135.5 (CH), 133.5 (CH), 130.6 (CH), 130.1 (C), 129.8 (CH), 128.7 (CH), 128.5 (CH), 127.7 (CH), 127.4 (CH), 97.6 (CH2), 93.1 (C), 79.7 (CH), 74.2 (CH), 74.1 (CH), 73.4 (CH), 69.9 (CH2), 56.0 (CH3), 45.7 (CH), 42.8 (C), 39.8 (CH2), 37.9 (C), 32.5 (CH2), 29.5 (CH3), 25.8 (CH2), 19.33 (CH3), 19.27 (CH3), 17.7 (CH3); HRMS (ESI): calcd for C36H42O8Na+ [M+Na]+ 625.2777, found 625.2777. |
| 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.Problematic one reflection with |I(obs)-I(calc)|/σW(I) greater than 10 (–2 3 1) has been omitted in the final refinement. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)
| x | y | z | Uiso*/Ueq | ||
| C1 | 0.2090 (2) | 0.1750 (2) | 0.91158 (15) | 0.0210 (5) | |
| C2 | 0.3204 (2) | 0.0817 (2) | 0.86310 (15) | 0.0198 (5) | |
| H2 | 0.3938 | 0.1143 | 0.8498 | 0.024* | |
| C3 | 0.2821 (2) | 0.0698 (2) | 0.76154 (15) | 0.0184 (4) | |
| H3 | 0.1858 | 0.1295 | 0.7447 | 0.022* | |
| C4 | 0.2914 (2) | −0.0675 (2) | 0.76837 (15) | 0.0207 (5) | |
| H4 | 0.3848 | −0.1344 | 0.7883 | 0.025* | |
| C5 | 0.2414 (2) | −0.0651 (2) | 0.66551 (15) | 0.0225 (5) | |
| H5B | 0.2627 | −0.1569 | 0.6672 | 0.027* | |
| H5A | 0.1431 | −0.0182 | 0.6578 | 0.027* | |
| C6 | 0.2999 (2) | 0.0002 (2) | 0.57150 (15) | 0.0214 (5) | |
| H6A | 0.3951 | −0.0565 | 0.5704 | 0.026* | |
| H6B | 0.2523 | 0.0104 | 0.5082 | 0.026* | |
| C7 | 0.2877 (2) | 0.1337 (2) | 0.57361 (15) | 0.0191 (5) | |
| H7 | 0.191 | 0.191 | 0.5717 | 0.023* | |
| C8 | 0.3583 (2) | 0.1246 (2) | 0.67110 (15) | 0.0183 (4) | |
| C9 | 0.3595 (2) | 0.2595 (2) | 0.66630 (16) | 0.0199 (5) | |
| H9B | 0.4203 | 0.242 | 0.7246 | 0.024* | |
| H9A | 0.4028 | 0.2871 | 0.6028 | 0.024* | |
| C10 | 0.2330 (2) | 0.3811 (2) | 0.66790 (16) | 0.0198 (5) | |
| H10 | 0.1778 | 0.413 | 0.602 | 0.024* | |
| C11 | 0.1476 (2) | 0.35654 (19) | 0.75632 (16) | 0.0197 (5) | |
| C12 | 0.0331 (2) | 0.3454 (2) | 0.73994 (15) | 0.0204 (5) | |
| C13 | −0.0137 (2) | 0.2618 (2) | 0.82427 (16) | 0.0230 (5) | |
| H13 | −0.1038 | 0.2705 | 0.8228 | 0.028* | |
| C14 | 0.0722 (2) | 0.1738 (2) | 0.90249 (16) | 0.0229 (5) | |
| H14 | 0.0479 | 0.1105 | 0.9525 | 0.027* | |
| C15 | 0.1993 (2) | 0.3171 (2) | 0.86995 (15) | 0.0207 (5) | |
| C16 | 0.3299 (2) | 0.3293 (2) | 0.88962 (16) | 0.0229 (5) | |
| H16B | 0.3555 | 0.2938 | 0.9636 | 0.034* | |
| H16C | 0.317 | 0.4222 | 0.865 | 0.034* | |
| H16A | 0.4005 | 0.2795 | 0.8529 | 0.034* | |
| C17 | 0.0958 (2) | 0.4076 (2) | 0.92429 (16) | 0.0243 (5) | |
| H17A | 0.0079 | 0.4077 | 0.9138 | 0.036* | |
| H17B | 0.092 | 0.4974 | 0.8955 | 0.036* | |
| H17C | 0.1216 | 0.3753 | 0.9981 | 0.036* | |
| C18 | −0.0437 (2) | 0.3934 (2) | 0.63817 (16) | 0.0255 (5) | |
| H18A | −0.0215 | 0.4638 | 0.5908 | 0.038* | |
| H18B | −0.1396 | 0.4273 | 0.648 | 0.038* | |
| H18C | −0.0202 | 0.3204 | 0.6094 | 0.038* | |
| C19 | 0.5062 (2) | 0.0313 (2) | 0.68131 (16) | 0.0211 (5) | |
| H19B | 0.5135 | −0.0561 | 0.6827 | 0.032* | |
| H19C | 0.5482 | 0.0244 | 0.7452 | 0.032* | |
| H19A | 0.5512 | 0.0659 | 0.6225 | 0.032* | |
| O20 | 0.36857 (14) | −0.04110 (14) | 0.94740 (10) | 0.0226 (3) | |
| C21 | 0.3358 (2) | −0.0133 (2) | 1.03550 (16) | 0.0229 (5) | |
| O22 | 0.25645 (14) | 0.11453 (14) | 1.01974 (10) | 0.0241 (3) | |
| O23 | 0.37257 (15) | −0.09211 (15) | 1.11907 (11) | 0.0301 (4) | |
| O24 | 0.34533 (13) | 0.19559 (14) | 0.48470 (10) | 0.0200 (3) | |
| C25 | 0.2682 (2) | 0.2569 (2) | 0.39610 (15) | 0.0204 (5) | |
| O26 | 0.16003 (15) | 0.25445 (15) | 0.38570 (11) | 0.0290 (4) | |
| C27 | 0.3292 (2) | 0.3303 (2) | 0.31322 (15) | 0.0192 (4) | |
| C28 | 0.2699 (2) | 0.3799 (2) | 0.21389 (16) | 0.0269 (5) | |
| H28 | 0.1964 | 0.362 | 0.1999 | 0.032* | |
| C29 | 0.3180 (2) | 0.4553 (2) | 0.13538 (17) | 0.0300 (5) | |
| H29 | 0.2785 | 0.4879 | 0.0673 | 0.036* | |
| C30 | 0.4233 (2) | 0.4832 (2) | 0.15603 (17) | 0.0299 (5) | |
| H30 | 0.4553 | 0.5363 | 0.1023 | 0.036* | |
| C31 | 0.4824 (2) | 0.4342 (2) | 0.25464 (17) | 0.0279 (5) | |
| H31 | 0.5552 | 0.4534 | 0.2684 | 0.033* | |
| C32 | 0.4363 (2) | 0.3575 (2) | 0.33317 (16) | 0.0218 (5) | |
| H32 | 0.4776 | 0.3234 | 0.4008 | 0.026* | |
| O33 | 0.28434 (14) | 0.47725 (14) | 0.66845 (11) | 0.0239 (3) | |
| C34 | 0.1863 (2) | 0.6092 (2) | 0.63828 (16) | 0.0246 (5) | |
| H34A | 0.1914 | 0.653 | 0.6887 | 0.029* | |
| H34B | 0.0964 | 0.6075 | 0.6389 | 0.029* | |
| C35 | 0.2054 (2) | 0.6865 (2) | 0.53358 (16) | 0.0217 (5) | |
| C36 | 0.1191 (2) | 0.8177 (2) | 0.49309 (17) | 0.0260 (5) | |
| H36 | 0.0481 | 0.8562 | 0.5317 | 0.031* | |
| C37 | 0.1356 (2) | 0.8926 (2) | 0.39732 (17) | 0.0313 (5) | |
| H37 | 0.0773 | 0.9827 | 0.3712 | 0.038* | |
| C38 | 0.2363 (2) | 0.8373 (3) | 0.33917 (18) | 0.0346 (6) | |
| H38 | 0.2465 | 0.8885 | 0.2727 | 0.041* | |
| C39 | 0.3217 (2) | 0.7074 (3) | 0.37825 (18) | 0.0334 (6) | |
| H39 | 0.3909 | 0.6689 | 0.3383 | 0.04* | |
| C40 | 0.3080 (2) | 0.6325 (2) | 0.47451 (17) | 0.0269 (5) | |
| H40 | 0.3688 | 0.5433 | 0.501 | 0.032* | |
| O41 | 0.20301 (14) | −0.09407 (14) | 0.84612 (10) | 0.0234 (3) | |
| C42 | 0.2292 (2) | −0.2270 (2) | 0.89614 (17) | 0.0287 (5) | |
| H42B | 0.194 | −0.2359 | 0.9653 | 0.034* | |
| H42A | 0.3269 | −0.2778 | 0.9054 | 0.034* | |
| O43 | 0.17233 (17) | −0.28080 (15) | 0.84205 (12) | 0.0328 (4) | |
| C44 | 0.0307 (2) | −0.2202 (2) | 0.83398 (19) | 0.0352 (6) | |
| H44C | −0.0029 | −0.2401 | 0.9026 | 0.053* | |
| H44A | −0.0046 | −0.254 | 0.7899 | 0.053* | |
| H44B | 0.0019 | −0.1246 | 0.8039 | 0.053* |
Atomic displacement parameters (Å2)
| U11 | U22 | U33 | U12 | U13 | U23 | |
| C1 | 0.0266 (11) | 0.0233 (12) | 0.0175 (11) | −0.0112 (9) | 0.0021 (9) | −0.0108 (9) |
| C2 | 0.0242 (11) | 0.0197 (11) | 0.0184 (11) | −0.0102 (9) | 0.0022 (9) | −0.0081 (9) |
| C3 | 0.0212 (10) | 0.0200 (11) | 0.0184 (10) | −0.0088 (9) | 0.0023 (8) | −0.0110 (9) |
| C4 | 0.0234 (11) | 0.0212 (12) | 0.0221 (11) | −0.0102 (9) | 0.0056 (9) | −0.0118 (9) |
| C5 | 0.0293 (12) | 0.0228 (12) | 0.0238 (11) | −0.0148 (10) | 0.0043 (9) | −0.0129 (9) |
| C6 | 0.0250 (11) | 0.0233 (12) | 0.0208 (11) | −0.0103 (9) | 0.0021 (9) | −0.0124 (9) |
| C7 | 0.0210 (11) | 0.0224 (11) | 0.0182 (11) | −0.0104 (9) | 0.0059 (9) | −0.0102 (9) |
| C8 | 0.0208 (11) | 0.0191 (11) | 0.0191 (10) | −0.0086 (9) | 0.0026 (8) | −0.0108 (9) |
| C9 | 0.0224 (11) | 0.0222 (12) | 0.0201 (11) | −0.0115 (9) | 0.0036 (9) | −0.0102 (9) |
| C10 | 0.0230 (11) | 0.0192 (11) | 0.0232 (11) | −0.0112 (9) | 0.0006 (9) | −0.0105 (9) |
| C11 | 0.0204 (11) | 0.0151 (11) | 0.0264 (11) | −0.0057 (9) | 0.0014 (9) | −0.0118 (9) |
| C12 | 0.0216 (11) | 0.0181 (11) | 0.0244 (11) | −0.0058 (9) | 0.0037 (9) | −0.0137 (9) |
| C13 | 0.0203 (11) | 0.0268 (12) | 0.0281 (12) | −0.0094 (10) | 0.0054 (9) | −0.0176 (10) |
| C14 | 0.0256 (12) | 0.0237 (12) | 0.0271 (12) | −0.0122 (10) | 0.0105 (10) | −0.0168 (10) |
| C15 | 0.0224 (11) | 0.0222 (12) | 0.0228 (11) | −0.0097 (9) | 0.0032 (9) | −0.0132 (9) |
| C16 | 0.0272 (12) | 0.0264 (12) | 0.0225 (11) | −0.0127 (10) | 0.0007 (9) | −0.0143 (9) |
| C17 | 0.0287 (12) | 0.0237 (12) | 0.0256 (12) | −0.0107 (10) | 0.0043 (9) | −0.0146 (10) |
| C18 | 0.0238 (11) | 0.0270 (13) | 0.0300 (12) | −0.0107 (10) | 0.0004 (10) | −0.0136 (10) |
| C19 | 0.0236 (11) | 0.0244 (12) | 0.0206 (11) | −0.0104 (9) | 0.0040 (9) | −0.0135 (9) |
| O20 | 0.0280 (8) | 0.0228 (8) | 0.0176 (7) | −0.0086 (7) | 0.0013 (6) | −0.0086 (6) |
| C21 | 0.0209 (11) | 0.0281 (13) | 0.0234 (12) | −0.0109 (10) | 0.0025 (9) | −0.0115 (10) |
| O22 | 0.0316 (8) | 0.0251 (9) | 0.0187 (8) | −0.0111 (7) | 0.0022 (6) | −0.0112 (6) |
| O23 | 0.0337 (9) | 0.0333 (9) | 0.0214 (9) | −0.0122 (7) | −0.0010 (7) | −0.0064 (7) |
| O24 | 0.0216 (7) | 0.0235 (8) | 0.0181 (7) | −0.0104 (6) | 0.0018 (6) | −0.0088 (6) |
| C25 | 0.0211 (11) | 0.0186 (11) | 0.0229 (11) | −0.0053 (9) | −0.0003 (9) | −0.0112 (9) |
| O26 | 0.0252 (9) | 0.0362 (10) | 0.0278 (8) | −0.0154 (7) | −0.0016 (7) | −0.0080 (7) |
| C27 | 0.0208 (11) | 0.0173 (11) | 0.0211 (11) | −0.0066 (9) | 0.0018 (9) | −0.0095 (9) |
| C28 | 0.0292 (12) | 0.0304 (13) | 0.0271 (12) | −0.0163 (11) | −0.0025 (10) | −0.0098 (10) |
| C29 | 0.0380 (14) | 0.0318 (14) | 0.0219 (12) | −0.0148 (11) | −0.0017 (10) | −0.0084 (10) |
| C30 | 0.0365 (13) | 0.0330 (13) | 0.0246 (12) | −0.0198 (11) | 0.0044 (10) | −0.0073 (10) |
| C31 | 0.0286 (12) | 0.0316 (13) | 0.0308 (13) | −0.0171 (11) | 0.0036 (10) | −0.0130 (10) |
| C32 | 0.0218 (11) | 0.0227 (12) | 0.0209 (11) | −0.0065 (9) | −0.0013 (9) | −0.0092 (9) |
| O33 | 0.0247 (8) | 0.0195 (8) | 0.0317 (8) | −0.0110 (7) | −0.0002 (6) | −0.0101 (7) |
| C34 | 0.0248 (11) | 0.0210 (12) | 0.0322 (12) | −0.0088 (10) | 0.0035 (10) | −0.0146 (10) |
| C35 | 0.0232 (11) | 0.0249 (12) | 0.0252 (11) | −0.0134 (9) | −0.0005 (9) | −0.0131 (9) |
| C36 | 0.0247 (12) | 0.0270 (13) | 0.0317 (13) | −0.0109 (10) | 0.0004 (10) | −0.0153 (10) |
| C37 | 0.0319 (13) | 0.0323 (14) | 0.0318 (13) | −0.0165 (11) | −0.0032 (11) | −0.0065 (11) |
| C38 | 0.0395 (14) | 0.0462 (16) | 0.0291 (13) | −0.0300 (13) | 0.0020 (11) | −0.0090 (12) |
| C39 | 0.0321 (13) | 0.0495 (17) | 0.0345 (14) | −0.0269 (13) | 0.0136 (11) | −0.0221 (12) |
| C40 | 0.0232 (12) | 0.0292 (13) | 0.0371 (13) | −0.0128 (10) | 0.0031 (10) | −0.0191 (11) |
| O41 | 0.0320 (8) | 0.0214 (8) | 0.0227 (8) | −0.0143 (7) | 0.0076 (6) | −0.0108 (6) |
| C42 | 0.0376 (13) | 0.0233 (13) | 0.0267 (12) | −0.0149 (11) | 0.0049 (10) | −0.0063 (10) |
| O43 | 0.0443 (10) | 0.0288 (9) | 0.0386 (9) | −0.0219 (8) | 0.0153 (8) | −0.0207 (7) |
| C44 | 0.0416 (15) | 0.0379 (15) | 0.0379 (14) | −0.0252 (12) | 0.0096 (11) | −0.0164 (12) |
Geometric parameters (Å, º)
| C1—O22 | 1.457 (2) | C18—H18B | 0.98 |
| C1—C14 | 1.514 (3) | C18—H18C | 0.98 |
| C1—C15 | 1.533 (3) | C19—H19B | 0.98 |
| C1—C2 | 1.548 (3) | C19—H19C | 0.98 |
| C2—O20 | 1.454 (2) | C19—H19A | 0.98 |
| C2—C3 | 1.537 (3) | O20—C21 | 1.334 (2) |
| C2—H2 | 1.0 | C21—O23 | 1.196 (3) |
| C3—C4 | 1.530 (3) | C21—O22 | 1.347 (3) |
| C3—C8 | 1.561 (3) | O24—C25 | 1.346 (2) |
| C3—H3 | 1.0 | C25—O26 | 1.213 (2) |
| C4—O41 | 1.438 (2) | C25—C27 | 1.490 (3) |
| C4—C5 | 1.530 (3) | C27—C32 | 1.389 (3) |
| C4—H4 | 1.0 | C27—C28 | 1.391 (3) |
| C5—C6 | 1.524 (3) | C28—C29 | 1.383 (3) |
| C5—H5B | 0.99 | C28—H28 | 0.95 |
| C5—H5A | 0.99 | C29—C30 | 1.379 (3) |
| C6—C7 | 1.512 (3) | C29—H29 | 0.95 |
| C6—H6A | 0.99 | C30—C31 | 1.382 (3) |
| C6—H6B | 0.99 | C30—H30 | 0.95 |
| C7—O24 | 1.456 (2) | C31—C32 | 1.379 (3) |
| C7—C8 | 1.537 (3) | C31—H31 | 0.95 |
| C7—H7 | 1.0 | C32—H32 | 0.95 |
| C8—C19 | 1.537 (3) | O33—C34 | 1.428 (2) |
| C8—C9 | 1.553 (3) | C34—C35 | 1.491 (3) |
| C9—C10 | 1.543 (3) | C34—H34A | 0.99 |
| C9—H9B | 0.99 | C34—H34B | 0.99 |
| C9—H9A | 0.99 | C35—C36 | 1.390 (3) |
| C10—O33 | 1.436 (2) | C35—C40 | 1.396 (3) |
| C10—C11 | 1.508 (3) | C36—C37 | 1.379 (3) |
| C10—H10 | 1.0 | C36—H36 | 0.95 |
| C11—C12 | 1.348 (3) | C37—C38 | 1.380 (3) |
| C11—C15 | 1.554 (3) | C37—H37 | 0.95 |
| C12—C13 | 1.473 (3) | C38—C39 | 1.374 (4) |
| C12—C18 | 1.502 (3) | C38—H38 | 0.95 |
| C13—C14 | 1.330 (3) | C39—C40 | 1.375 (3) |
| C13—H13 | 0.95 | C39—H39 | 0.95 |
| C14—H14 | 0.95 | C40—H40 | 0.95 |
| C15—C16 | 1.537 (3) | O41—C42 | 1.400 (3) |
| C15—C17 | 1.541 (3) | C42—O43 | 1.405 (3) |
| C16—H16B | 0.98 | C42—H42B | 0.99 |
| C16—H16C | 0.98 | C42—H42A | 0.99 |
| C16—H16A | 0.98 | O43—C44 | 1.421 (3) |
| C17—H17A | 0.98 | C44—H44C | 0.98 |
| C17—H17B | 0.98 | C44—H44A | 0.98 |
| C17—H17C | 0.98 | C44—H44B | 0.98 |
| C18—H18A | 0.98 | ||
| O22—C1—C14 | 107.39 (16) | C15—C17—H17A | 109.5 |
| O22—C1—C15 | 112.26 (16) | C15—C17—H17B | 109.5 |
| C14—C1—C15 | 109.44 (17) | H17A—C17—H17B | 109.5 |
| O22—C1—C2 | 100.39 (15) | C15—C17—H17C | 109.5 |
| C14—C1—C2 | 115.12 (16) | H17A—C17—H17C | 109.5 |
| C15—C1—C2 | 111.91 (17) | H17B—C17—H17C | 109.5 |
| O20—C2—C3 | 114.77 (16) | C12—C18—H18A | 109.5 |
| O20—C2—C1 | 102.39 (15) | C12—C18—H18B | 109.5 |
| C3—C2—C1 | 116.91 (17) | H18A—C18—H18B | 109.5 |
| O20—C2—H2 | 107.4 | C12—C18—H18C | 109.5 |
| C3—C2—H2 | 107.4 | H18A—C18—H18C | 109.5 |
| C1—C2—H2 | 107.4 | H18B—C18—H18C | 109.5 |
| C4—C3—C2 | 114.36 (16) | C8—C19—H19B | 109.5 |
| C4—C3—C8 | 112.76 (16) | C8—C19—H19C | 109.5 |
| C2—C3—C8 | 111.37 (16) | H19B—C19—H19C | 109.5 |
| C4—C3—H3 | 105.9 | C8—C19—H19A | 109.5 |
| C2—C3—H3 | 105.9 | H19B—C19—H19A | 109.5 |
| C8—C3—H3 | 105.9 | H19C—C19—H19A | 109.5 |
| O41—C4—C3 | 104.79 (15) | C21—O20—C2 | 108.37 (16) |
| O41—C4—C5 | 109.40 (16) | O23—C21—O20 | 124.3 (2) |
| C3—C4—C5 | 109.75 (17) | O23—C21—O22 | 123.56 (19) |
| O41—C4—H4 | 110.9 | O20—C21—O22 | 112.13 (18) |
| C3—C4—H4 | 110.9 | C21—O22—C1 | 108.85 (15) |
| C5—C4—H4 | 110.9 | C25—O24—C7 | 116.56 (15) |
| C6—C5—C4 | 114.71 (17) | O26—C25—O24 | 123.60 (19) |
| C6—C5—H5B | 108.6 | O26—C25—C27 | 123.88 (19) |
| C4—C5—H5B | 108.6 | O24—C25—C27 | 112.51 (17) |
| C6—C5—H5A | 108.6 | C32—C27—C28 | 119.65 (19) |
| C4—C5—H5A | 108.6 | C32—C27—C25 | 122.37 (18) |
| H5B—C5—H5A | 107.6 | C28—C27—C25 | 117.85 (19) |
| C7—C6—C5 | 110.62 (16) | C29—C28—C27 | 120.1 (2) |
| C7—C6—H6A | 109.5 | C29—C28—H28 | 120.0 |
| C5—C6—H6A | 109.5 | C27—C28—H28 | 120.0 |
| C7—C6—H6B | 109.5 | C30—C29—C28 | 120.0 (2) |
| C5—C6—H6B | 109.5 | C30—C29—H29 | 120.0 |
| H6A—C6—H6B | 108.1 | C28—C29—H29 | 120.0 |
| O24—C7—C6 | 110.82 (15) | C29—C30—C31 | 120.2 (2) |
| O24—C7—C8 | 108.01 (15) | C29—C30—H30 | 119.9 |
| C6—C7—C8 | 112.06 (17) | C31—C30—H30 | 119.9 |
| O24—C7—H7 | 108.6 | C32—C31—C30 | 120.3 (2) |
| C6—C7—H7 | 108.6 | C32—C31—H31 | 119.8 |
| C8—C7—H7 | 108.6 | C30—C31—H31 | 119.8 |
| C19—C8—C7 | 110.94 (16) | C31—C32—C27 | 119.86 (19) |
| C19—C8—C9 | 104.78 (16) | C31—C32—H32 | 120.1 |
| C7—C8—C9 | 111.49 (16) | C27—C32—H32 | 120.1 |
| C19—C8—C3 | 110.89 (16) | C34—O33—C10 | 113.59 (15) |
| C7—C8—C3 | 104.62 (15) | O33—C34—C35 | 111.86 (17) |
| C9—C8—C3 | 114.26 (16) | O33—C34—H34A | 109.2 |
| C10—C9—C8 | 123.76 (17) | C35—C34—H34A | 109.2 |
| C10—C9—H9B | 106.4 | O33—C34—H34B | 109.2 |
| C8—C9—H9B | 106.4 | C35—C34—H34B | 109.2 |
| C10—C9—H9A | 106.4 | H34A—C34—H34B | 107.9 |
| C8—C9—H9A | 106.4 | C36—C35—C40 | 118.3 (2) |
| H9B—C9—H9A | 106.5 | C36—C35—C34 | 119.20 (19) |
| O33—C10—C11 | 113.16 (16) | C40—C35—C34 | 122.5 (2) |
| O33—C10—C9 | 103.42 (15) | C37—C36—C35 | 120.6 (2) |
| C11—C10—C9 | 114.58 (17) | C37—C36—H36 | 119.7 |
| O33—C10—H10 | 108.5 | C35—C36—H36 | 119.7 |
| C11—C10—H10 | 108.5 | C36—C37—C38 | 120.4 (2) |
| C9—C10—H10 | 108.5 | C36—C37—H37 | 119.8 |
| C12—C11—C10 | 119.94 (18) | C38—C37—H37 | 119.8 |
| C12—C11—C15 | 117.22 (18) | C39—C38—C37 | 119.4 (2) |
| C10—C11—C15 | 121.82 (17) | C39—C38—H38 | 120.3 |
| C11—C12—C13 | 118.68 (19) | C37—C38—H38 | 120.3 |
| C11—C12—C18 | 126.2 (2) | C38—C39—C40 | 120.7 (2) |
| C13—C12—C18 | 114.38 (18) | C38—C39—H39 | 119.6 |
| C14—C13—C12 | 118.85 (19) | C40—C39—H39 | 119.6 |
| C14—C13—H13 | 120.6 | C39—C40—C35 | 120.5 (2) |
| C12—C13—H13 | 120.6 | C39—C40—H40 | 119.8 |
| C13—C14—C1 | 119.8 (2) | C35—C40—H40 | 119.8 |
| C13—C14—H14 | 120.1 | C42—O41—C4 | 116.28 (16) |
| C1—C14—H14 | 120.1 | O41—C42—O43 | 112.97 (18) |
| C1—C15—C16 | 112.74 (17) | O41—C42—H42B | 109.0 |
| C1—C15—C17 | 111.81 (17) | O43—C42—H42B | 109.0 |
| C16—C15—C17 | 104.00 (16) | O41—C42—H42A | 109.0 |
| C1—C15—C11 | 101.58 (15) | O43—C42—H42A | 109.0 |
| C16—C15—C11 | 117.71 (17) | H42B—C42—H42A | 107.8 |
| C17—C15—C11 | 109.19 (17) | C42—O43—C44 | 112.09 (17) |
| C15—C16—H16B | 109.5 | O43—C44—H44C | 109.5 |
| C15—C16—H16C | 109.5 | O43—C44—H44A | 109.5 |
| H16B—C16—H16C | 109.5 | H44C—C44—H44A | 109.5 |
| C15—C16—H16A | 109.5 | O43—C44—H44B | 109.5 |
| H16B—C16—H16A | 109.5 | H44C—C44—H44B | 109.5 |
| H16C—C16—H16A | 109.5 | H44A—C44—H44B | 109.5 |
| O22—C1—C2—O20 | 26.87 (18) | C3—C8—C9—C10 | −51.5 (3) |
| C14—C1—C2—O20 | −88.07 (19) | C8—C9—C10—O33 | 176.60 (17) |
| C15—C1—C2—O20 | 146.14 (16) | C8—C9—C10—C11 | 53.0 (3) |
| O22—C1—C2—C3 | 153.21 (16) | O33—C10—C11—C12 | 137.37 (19) |
| C14—C1—C2—C3 | 38.3 (3) | C9—C10—C11—C12 | −104.4 (2) |
| C15—C1—C2—C3 | −87.5 (2) | O33—C10—C11—C15 | −54.5 (2) |
| O20—C2—C3—C4 | 4.3 (2) | C9—C10—C11—C15 | 63.8 (2) |
| C1—C2—C3—C4 | −115.6 (2) | C10—C11—C12—C13 | 150.34 (18) |
| O20—C2—C3—C8 | −124.98 (18) | C15—C11—C12—C13 | −18.4 (3) |
| C1—C2—C3—C8 | 115.07 (19) | C10—C11—C12—C18 | −19.5 (3) |
| C2—C3—C4—O41 | 58.5 (2) | C15—C11—C12—C18 | 171.80 (18) |
| C8—C3—C4—O41 | −172.95 (15) | C11—C12—C13—C14 | −17.7 (3) |
| C2—C3—C4—C5 | 175.84 (17) | C18—C12—C13—C14 | 153.33 (19) |
| C8—C3—C4—C5 | −55.6 (2) | C12—C13—C14—C1 | 9.1 (3) |
| O41—C4—C5—C6 | 163.01 (17) | O22—C1—C14—C13 | 155.28 (18) |
| C3—C4—C5—C6 | 48.5 (2) | C15—C1—C14—C13 | 33.2 (2) |
| C4—C5—C6—C7 | −50.2 (2) | C2—C1—C14—C13 | −93.9 (2) |
| C5—C6—C7—O24 | 179.13 (16) | O22—C1—C15—C16 | 53.1 (2) |
| C5—C6—C7—C8 | 58.4 (2) | C14—C1—C15—C16 | 172.27 (16) |
| O24—C7—C8—C19 | −65.5 (2) | C2—C1—C15—C16 | −58.9 (2) |
| C6—C7—C8—C19 | 56.9 (2) | O22—C1—C15—C17 | −63.6 (2) |
| O24—C7—C8—C9 | 50.9 (2) | C14—C1—C15—C17 | 55.5 (2) |
| C6—C7—C8—C9 | 173.24 (16) | C2—C1—C15—C17 | −175.65 (16) |
| O24—C7—C8—C3 | 174.89 (15) | O22—C1—C15—C11 | −179.97 (16) |
| C6—C7—C8—C3 | −62.8 (2) | C14—C1—C15—C11 | −60.82 (19) |
| C4—C3—C8—C19 | −57.8 (2) | C2—C1—C15—C11 | 68.0 (2) |
| C2—C3—C8—C19 | 72.3 (2) | C12—C11—C15—C1 | 56.4 (2) |
| C4—C3—C8—C7 | 61.8 (2) | C10—C11—C15—C1 | −112.1 (2) |
| C2—C3—C8—C7 | −168.02 (16) | C12—C11—C15—C16 | 179.97 (18) |
| C4—C3—C8—C9 | −175.95 (16) | C10—C11—C15—C16 | 11.5 (3) |
| C2—C3—C8—C9 | −45.8 (2) | C12—C11—C15—C17 | −61.8 (2) |
| C19—C8—C9—C10 | −173.02 (18) | C10—C11—C15—C17 | 129.69 (19) |
| C7—C8—C9—C10 | 66.9 (2) | C3—C2—O20—C21 | −149.52 (17) |
Hydrogen-bond geometry (Å, º)
Cg is the centroid of the C35–C40 benzene ring.
| D—H···A | D—H | H···A | D···A | D—H···A |
| C34—H34A···O43i | 0.99 | 2.42 | 3.377 (3) | 163 |
| C38—H38···O23ii | 0.95 | 2.44 | 3.295 (3) | 149 |
| C31—H31···O33iii | 0.95 | 2.49 | 3.426 (3) | 168 |
| C2—H2···O23iv | 1.00 | 2.51 | 3.433 (3) | 153 |
| C16—H16A···O23iv | 0.98 | 2.53 | 3.357 (3) | 142 |
| C19—H19C···O23iv | 0.98 | 2.54 | 3.477 (3) | 160 |
| C18—H18C···Cgv | 0.98 | 2.89 | 3.492 (3) | 121 |
Symmetry codes: (i) x, y+1, z; (ii) x, y+1, z−1; (iii) −x+1, −y+1, −z+1; (iv) −x+1, −y, −z+2; (v) −x, −y+1, −z+1.
References
- Bruker (2014). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
- Fukaya, K., Sugai, T., Yamaguchi, Y., Watanabe, A., Sato, T. & Chida, N. (2015). In preparation.
- Groom, C. R. & Allen, F. H. (2014). Angew. Chem. Int. Ed. 53, 662–671. [DOI] [PubMed]
- Keil, J. M., Massa, W., Riedel, R., Seitz, G. & Wocadlo, S. (1994). Tetrahedron Lett. 35, 7923–7926.
- 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.
- Nicolaou, K. C., Liu, J.-J., Yang, Z., Ueno, H., Sorensen, E. J., Claiborne, C. F., Guy, R. K., Hwang, C.-K., Nakada, M. & Nantermet, P. G. (1995). J. Am. Chem. Soc. 117, 634–644.
- Nicolaou, K. C., Ueno, H., Liu, J.-J., Nantermet, P. G., Yang, Z., Renaud, J., Paulvannan, K. & Chadha, R. (1995). J. Am. Chem. Soc. 117, 653–659.
- Nicolaou, K. C., Yang, Z., Liu, J.-J., Nantermet, P. G., Claiborne, C. F., Renaud, J., Guy, R. K. & Shibayama, K. (1995). J. Am. Chem. Soc. 117, 645–652.
- Ohba, S., Chinen, A., Matsumoto, Y. & Chida, N. (2003). Acta Cryst. E59, o1476–o1477.
- Oishi, T., Fukaya, K., Yamaguchi, Y., Sugai, T., Watanabe, A., Sato, T. & Chida, N. (2015). Acta Cryst. E71, 466–472. [DOI] [PMC free article] [PubMed]
- Oishi, T., Yamaguchi, Y., Fukaya, K., Sugai, T., Watanabe, A., Sato, T. & Chida, N. (2015). Acta Cryst. E71, 8–11. [DOI] [PMC free article] [PubMed]
- Paquette, L. A. & Zhao, M. (1998). J. Am. Chem. Soc. 120, 5203–5212.
- Poujol, H., Ahond, A., Al Mourabit, A., Chiaroni, A., Poupat, C., Riche, C. & Potier, P. (1997). Tetrahedron, 53, 5169–5184.
- Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [DOI] [PubMed]
- Sheldrick, G. M. (2015). Acta Cryst. C71, 3–8.
- Spek, A. L. (2009). Acta Cryst. D65, 148–155. [DOI] [PMC free article] [PubMed]
- Wall, M. E. & Wani, M. C. (1995). ACS Symp. Ser. 583, 18–30.
- Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925.
Associated Data
This section collects any data citations, data availability statements, or supplementary materials included in this article.
Supplementary Materials
Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S2056989015007136/is5396sup1.cif
Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015007136/is5396Isup2.hkl
CCDC reference: 1058739
Additional supporting information: crystallographic information; 3D view; checkCIF report