# Supplementary Material (ESI) for Chemical Communications
# This journal is (c) The Royal Society of Chemistry 2010
data_global
_journal_name_full Chem.Commun.
_journal_coden_cambridge 0182
_publ_contact_author_name
;Marinetti, Angela
;
_publ_contact_author_address
;Centre de Recherche de Gif
Institut de Chimie des Substances Naturelles-CNRS
1 avenue de la Terrasse
91198 Gif sur Yvette
France
;
_publ_contact_author_email angela.marinetti@icsn.cnrs-gif.fr
_publ_contact_author_phone +33169823036
_publ_contact_author_fax +33169077247
loop_
_publ_author_name
_publ_author_address
N.Pinto
;Institut de Chimie des Substances Naturelles-CNRS
1 avenue de la Terrasse
91198 Gif sur Yvette
France
;
P.Retailleau
;Institut de Chimie des Substances Naturelles-CNRS
1 avenue de la Terrasse
91198 Gif sur Yvette
France
;
A.Voituriez
;Institut de Chimie des Substances Naturelles-CNRS
1 avenue de la Terrasse
91198 Gif sur Yvette
France
;
A.Marinetti
;Institut de Chimie des Substances Naturelles-CNRS
1 avenue de la Terrasse
91198 Gif sur Yvette
France
;
_audit_creation_date 09-08-10
_publ_contact_letter
;
;
_publ_requested_category FM
_publ_section_title
;
Organocatalytic Enantioselective Desymmetrization of Cyclic Enones
via Phosphine Promoted [3+2] Annulations
;
_publ_section_abstract
; ?
;
_publ_section_comment
; ?
;
_publ_section_exptl_prep
; ?
;
_publ_section_exptl_refinement
; ?
;
_publ_section_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.
Nonius, B. V. (1999). COLLECT, data collection software.
Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Volume 276,
Macromolecular Crystallography, part A, edited by C.W. Carter, Jr. & R.M.
Sweet, 307-326, 1997, New York: Academic Press.
Sheldrick, G.M. (2008).Acta Cryst. A64, 112-122.
Spek, A. L. (2003). J.Appl. Cryst. 36, 7-13.
Welter, R. (2006). The Crystalbuilder Project
Acta Cryst. A62, s252.
;
_publ_section_figure_captions
; ?
;
_publ_section_acknowledgements
; ?
;
data_npt524
_database_code_depnum_ccdc_archive 'CCDC 787941'
#TrackingRef '2071_web_deposit_cif_file_0_PascalRETAILLEAU_1281344269.cif'
_audit_creation_method SHELXL-97
_chemical_name_systematic
;
(4R,9R,E)-ethyl 7-benzylidene-9-methyl-6-oxo-4-phenylspiro
[4.5]dec-1-ene-1-carboxylate
;
_chemical_name_common ?
_chemical_melting_point ?
_chemical_formula_moiety 'C27 H28 O3'
_chemical_formula_sum 'C27 H28 O3'
_chemical_formula_weight 400.49
_chemical_absolute_configuration .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_symmetry_cell_setting triclinic
_symmetry_space_group_name_H-M 'P -1'
_symmetry_space_group_name_Hall '-P 1'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
_cell_length_a 6.273(3)
_cell_length_b 10.862(4)
_cell_length_c 16.439(4)
_cell_angle_alpha 89.178(2)
_cell_angle_beta 81.131(8)
_cell_angle_gamma 89.707(5)
_cell_volume 1106.6(7)
_cell_formula_units_Z 2
_cell_measurement_temperature 293(2)
_cell_measurement_reflns_used 3101
_cell_measurement_theta_min 0.998
_cell_measurement_theta_max 26.022
_exptl_crystal_description 'parallelepipedic block'
_exptl_crystal_colour colourless
_exptl_crystal_size_max 0.58
_exptl_crystal_size_mid 0.32
_exptl_crystal_size_min 0.17
_exptl_crystal_density_meas ?
_exptl_crystal_density_diffrn 1.202
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 428
_exptl_absorpt_coefficient_mu 0.077
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_correction_T_min 0.887
_exptl_absorpt_correction_T_max 0.987
_exptl_absorpt_process_details 'Scalepack (Otwinowski & Minor, 1997)'
_exptl_special_details
;
?
;
_diffrn_ambient_temperature 293(2)
_diffrn_radiation_wavelength 0.71069
_diffrn_radiation_type MoK\a
_diffrn_radiation_source 'fine-focus sealed tube'
_diffrn_radiation_monochromator graphite
_diffrn_measurement_device_type 'Nonius kappa-CCD diffractometer'
_diffrn_measurement_method 'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time ?
_diffrn_standards_decay_% ?
_diffrn_reflns_number 18785
_diffrn_reflns_av_R_equivalents 0.0254
_diffrn_reflns_av_sigmaI/netI 0.0352
_diffrn_reflns_limit_h_min -6
_diffrn_reflns_limit_h_max 7
_diffrn_reflns_limit_k_min -13
_diffrn_reflns_limit_k_max 12
_diffrn_reflns_limit_l_min -19
_diffrn_reflns_limit_l_max 19
_diffrn_reflns_theta_min 2.27
_diffrn_reflns_theta_max 25.30
_reflns_number_total 4005
_reflns_number_gt 2871
_reflns_threshold_expression >2sigma(I)
_computing_data_collection
'DENZO (Otwinowski & Minor, 1997); COLLECT (Nonius B.V., 1999)'
_computing_cell_refinement
'DENZO (Otwinowski & Minor, 1997); COLLECT (Nonius B.V., 1999)'
_computing_data_reduction 'SCALEPACK (Otwinowski & Minor, 1997)'
_computing_structure_solution 'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement
'SHELXL97 (Sheldrick, 2008); CRYSTALBUILDER (Welter, 2006)'
_computing_molecular_graphics 'PLATON (Spek, 2003)'
_computing_publication_material 'SHELXL97 (Sheldrick, 2008)'
_refine_special_details
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type full
_refine_ls_weighting_scheme calc
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0718P)^2^+0.2490P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_atom_sites_solution_hydrogens difmap
_refine_ls_hydrogen_treatment constr
_refine_ls_extinction_method SHELXL
_refine_ls_extinction_coef 0.046(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_number_reflns 4005
_refine_ls_number_parameters 283
_refine_ls_number_restraints 2
_refine_ls_R_factor_all 0.0750
_refine_ls_R_factor_gt 0.0504
_refine_ls_wR_factor_ref 0.1458
_refine_ls_wR_factor_gt 0.1290
_refine_ls_goodness_of_fit_ref 1.034
_refine_ls_restrained_S_all 1.067
_refine_ls_shift/su_max 0.000
_refine_ls_shift/su_mean 0.000
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O11 O 0.3530(2) -0.04448(14) 0.84387(9) 0.0632(4) Uani 1 1 d . . .
O27 O -0.0952(3) -0.21268(14) 0.81568(10) 0.0703(5) Uani 1 1 d . . .
O28 O -0.2886(3) -0.20365(15) 0.94248(10) 0.0746(5) Uani 1 1 d . A .
C1 C 0.0253(3) 0.04736(16) 0.81867(11) 0.0422(4) Uani 1 1 d . . .
C2 C -0.0985(3) 0.07558(19) 0.74672(12) 0.0504(5) Uani 1 1 d . . .
H2A H -0.1968 0.0082 0.7424 0.061 Uiso 1 1 calc R . .
H2B H -0.1848 0.1491 0.7595 0.061 Uiso 1 1 calc R . .
C3 C 0.0403(3) 0.09447(19) 0.66458(13) 0.0550(5) Uani 1 1 d . . .
H3 H 0.1409 0.1621 0.6684 0.066 Uiso 1 1 calc R . .
C13 C -0.0990(5) 0.1267(3) 0.59872(15) 0.0796(8) Uani 1 1 d . . .
H13A H -0.2033 0.0629 0.5968 0.119 Uiso 1 1 calc R . .
H13B H -0.0090 0.1341 0.5461 0.119 Uiso 1 1 calc R . .
H13C H -0.1722 0.2034 0.6119 0.119 Uiso 1 1 calc R . .
C4 C 0.1677(3) -0.02236(19) 0.64128(12) 0.0528(5) Uani 1 1 d . . .
H4A H 0.0687 -0.0861 0.6302 0.063 Uiso 1 1 calc R . .
H4B H 0.2669 -0.0069 0.5908 0.063 Uiso 1 1 calc R . .
C5 C 0.2935(3) -0.06885(16) 0.70605(11) 0.0426(4) Uani 1 1 d . . .
C6 C 0.2366(3) -0.02398(17) 0.79236(12) 0.0443(4) Uani 1 1 d . . .
C7 C -0.1204(3) -0.02417(18) 0.88586(12) 0.0473(5) Uani 1 1 d . . .
C8 C -0.2058(3) 0.0467(2) 0.94726(13) 0.0542(5) Uani 1 1 d . . .
H8 H -0.3006 0.0189 0.9929 0.065 Uiso 1 1 calc R . .
C9 C -0.1320(3) 0.1758(2) 0.93438(13) 0.0569(5) Uani 1 1 d . . .
H9A H -0.0970 0.2101 0.9848 0.068 Uiso 1 1 calc R . .
H9B H -0.2408 0.2269 0.9145 0.068 Uiso 1 1 calc R . .
C10 C 0.0703(3) 0.16435(17) 0.86895(12) 0.0463(5) Uani 1 1 d . . .
H10 H 0.1885 0.1415 0.8989 0.056 Uiso 1 1 calc R . .
C12 C 0.1440(3) 0.27811(18) 0.81923(12) 0.0509(5) Uani 1 1 d . . .
C14 C 0.4542(3) -0.15185(17) 0.69465(12) 0.0460(5) Uani 1 1 d . . .
H14 H 0.5182 -0.1674 0.7412 0.055 Uiso 1 1 calc R . .
C15 C 0.5476(3) -0.22251(17) 0.62234(12) 0.0488(5) Uani 1 1 d . . .
C16 C 0.3594(4) 0.2903(2) 0.78598(15) 0.0655(6) Uani 1 1 d . . .
H16 H 0.4560 0.2288 0.7960 0.079 Uiso 1 1 calc R . .
C17 C 0.4349(5) 0.3913(3) 0.73840(18) 0.0862(8) Uani 1 1 d . . .
H17 H 0.5801 0.3963 0.7160 0.103 Uiso 1 1 calc R . .
C18 C 0.2952(6) 0.4846(3) 0.7242(2) 0.0957(10) Uani 1 1 d . . .
H18 H 0.3450 0.5531 0.6925 0.115 Uiso 1 1 calc R . .
C19 C 0.0828(6) 0.4749(3) 0.7572(2) 0.1003(10) Uani 1 1 d . . .
H19 H -0.0123 0.5377 0.7481 0.120 Uiso 1 1 calc R . .
C20 C 0.0065(4) 0.3729(2) 0.80429(17) 0.0760(7) Uani 1 1 d . . .
H20 H -0.1391 0.3681 0.8261 0.091 Uiso 1 1 calc R . .
C21 C 0.7374(4) -0.2858(2) 0.62700(15) 0.0629(6) Uani 1 1 d . . .
H21 H 0.8021 -0.2793 0.6740 0.075 Uiso 1 1 calc R . .
C22 C 0.8323(5) -0.3583(3) 0.56344(18) 0.0856(8) Uani 1 1 d . . .
H22 H 0.9604 -0.3997 0.5677 0.103 Uiso 1 1 calc R . .
C23 C 0.7388(5) -0.3696(3) 0.49403(19) 0.0916(9) Uani 1 1 d . . .
H23 H 0.8025 -0.4190 0.4512 0.110 Uiso 1 1 calc R . .
C24 C 0.5533(5) -0.3085(3) 0.48794(17) 0.0900(9) Uani 1 1 d . . .
H24 H 0.4906 -0.3155 0.4405 0.108 Uiso 1 1 calc R . .
C25 C 0.4563(4) -0.2361(2) 0.55138(15) 0.0736(7) Uani 1 1 d . . .
H25 H 0.3277 -0.1957 0.5465 0.088 Uiso 1 1 calc R . .
C26 C -0.1641(3) -0.1551(2) 0.87617(13) 0.0553(5) Uani 1 1 d . . .
C29 C -0.3310(7) -0.3356(3) 0.9404(2) 0.1100(12) Uani 1 1 d D . .
H29A H -0.2000 -0.3769 0.9157 0.132 Uiso 0.676(7) 1 calc PR A 1
H29B H -0.3667 -0.3663 0.9966 0.132 Uiso 0.676(7) 1 calc PR A 1
H29C H -0.4714 -0.3502 0.9730 0.132 Uiso 0.324(7) 1 calc PR A 2
H29D H -0.3433 -0.3556 0.8840 0.132 Uiso 0.324(7) 1 calc PR A 2
C30A C -0.4975(8) -0.3669(4) 0.8971(3) 0.1045(19) Uani 0.676(7) 1 d PD A 1
H30A H -0.5154 -0.4547 0.8986 0.157 Uiso 0.676(7) 1 calc PR A 1
H30B H -0.4623 -0.3390 0.8410 0.157 Uiso 0.676(7) 1 calc PR A 1
H30C H -0.6292 -0.3285 0.9220 0.157 Uiso 0.676(7) 1 calc PR A 1
C30B C -0.1875(19) -0.4198(8) 0.9672(8) 0.124(5) Uani 0.324(7) 1 d PD A 2
H30D H -0.2394 -0.5019 0.9623 0.185 Uiso 0.324(7) 1 calc PR A 2
H30E H -0.1760 -0.4045 1.0237 0.185 Uiso 0.324(7) 1 calc PR A 2
H30F H -0.0483 -0.4109 0.9341 0.185 Uiso 0.324(7) 1 calc PR A 2
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O11 0.0620(9) 0.0874(10) 0.0446(8) -0.0142(7) -0.0220(7) 0.0301(8)
O27 0.0864(11) 0.0621(9) 0.0596(10) -0.0097(8) -0.0018(8) -0.0046(8)
O28 0.0915(11) 0.0694(10) 0.0591(10) 0.0016(8) 0.0012(9) -0.0228(8)
C1 0.0402(9) 0.0503(10) 0.0373(10) -0.0049(8) -0.0092(8) 0.0057(8)
C2 0.0459(10) 0.0615(12) 0.0462(12) -0.0059(9) -0.0146(9) 0.0123(9)
C3 0.0602(12) 0.0610(12) 0.0462(12) 0.0020(9) -0.0158(9) 0.0098(10)
C13 0.0936(18) 0.0953(18) 0.0552(15) 0.0002(13) -0.0296(13) 0.0325(15)
C4 0.0583(11) 0.0638(12) 0.0376(11) -0.0041(9) -0.0115(9) 0.0135(10)
C5 0.0434(9) 0.0474(10) 0.0376(10) -0.0037(8) -0.0080(8) 0.0037(8)
C6 0.0448(10) 0.0497(10) 0.0400(11) -0.0028(8) -0.0110(8) 0.0070(8)
C7 0.0452(10) 0.0575(11) 0.0407(11) -0.0029(9) -0.0111(8) 0.0010(8)
C8 0.0466(10) 0.0730(14) 0.0420(11) -0.0031(10) -0.0038(9) 0.0013(9)
C9 0.0569(12) 0.0667(13) 0.0464(12) -0.0112(10) -0.0048(9) 0.0113(10)
C10 0.0455(10) 0.0520(11) 0.0428(11) -0.0076(8) -0.0107(8) 0.0087(8)
C12 0.0583(11) 0.0496(11) 0.0464(12) -0.0091(9) -0.0127(9) 0.0030(9)
C14 0.0469(10) 0.0515(11) 0.0409(11) -0.0039(8) -0.0104(8) 0.0053(8)
C15 0.0511(10) 0.0468(10) 0.0481(12) -0.0045(9) -0.0064(9) 0.0064(8)
C16 0.0583(13) 0.0693(14) 0.0696(16) -0.0016(12) -0.0124(11) -0.0047(11)
C17 0.0865(18) 0.092(2) 0.0804(19) 0.0073(15) -0.0121(15) -0.0318(16)
C18 0.136(3) 0.0679(17) 0.085(2) 0.0130(15) -0.023(2) -0.0287(18)
C19 0.134(3) 0.0632(16) 0.104(2) 0.0140(16) -0.020(2) 0.0195(18)
C20 0.0783(16) 0.0626(14) 0.0849(18) 0.0067(13) -0.0068(13) 0.0178(12)
C21 0.0644(13) 0.0637(13) 0.0613(14) -0.0083(11) -0.0122(11) 0.0198(11)
C22 0.0842(17) 0.0909(18) 0.0812(19) -0.0230(15) -0.0108(15) 0.0419(15)
C23 0.106(2) 0.0936(19) 0.0732(19) -0.0327(15) -0.0072(16) 0.0399(17)
C24 0.107(2) 0.105(2) 0.0633(17) -0.0363(15) -0.0292(15) 0.0409(17)
C25 0.0788(15) 0.0863(16) 0.0605(15) -0.0274(13) -0.0250(12) 0.0334(13)
C26 0.0575(12) 0.0647(13) 0.0446(12) 0.0004(10) -0.0109(10) -0.0051(10)
C29 0.145(3) 0.088(2) 0.087(2) 0.0004(18) 0.015(2) -0.044(2)
C30A 0.123(4) 0.089(3) 0.099(4) -0.015(3) -0.009(3) -0.036(3)
C30B 0.174(12) 0.065(6) 0.131(10) -0.013(6) -0.021(9) -0.004(7)
_geom_special_details
;
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.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O11 C6 1.218(2) . ?
O27 C26 1.204(3) . ?
O28 C26 1.342(3) . ?
O28 C29 1.461(4) . ?
C1 C7 1.526(3) . ?
C1 C2 1.538(3) . ?
C1 C6 1.538(2) . ?
C1 C10 1.576(3) . ?
C2 C3 1.501(3) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.518(3) . ?
C3 C13 1.528(3) . ?
C3 H3 0.9800 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C4 C5 1.500(3) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C14 1.343(3) . ?
C5 C6 1.497(3) . ?
C7 C8 1.323(3) . ?
C7 C26 1.466(3) . ?
C8 C9 1.481(3) . ?
C8 H8 0.9300 . ?
C9 C10 1.538(3) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C12 1.506(3) . ?
C10 H10 0.9800 . ?
C12 C20 1.383(3) . ?
C12 C16 1.383(3) . ?
C14 C15 1.467(3) . ?
C14 H14 0.9300 . ?
C15 C21 1.384(3) . ?
C15 C25 1.387(3) . ?
C16 C17 1.380(4) . ?
C16 H16 0.9300 . ?
C17 C18 1.377(5) . ?
C17 H17 0.9300 . ?
C18 C19 1.363(5) . ?
C18 H18 0.9300 . ?
C19 C20 1.386(4) . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?
C21 C22 1.376(3) . ?
C21 H21 0.9300 . ?
C22 C23 1.368(4) . ?
C22 H22 0.9300 . ?
C23 C24 1.353(4) . ?
C23 H23 0.9300 . ?
C24 C25 1.379(3) . ?
C24 H24 0.9300 . ?
C25 H25 0.9300 . ?
C29 C30B 1.394(8) . ?
C29 C30A 1.398(5) . ?
C29 H29A 0.9700 . ?
C29 H29B 0.9700 . ?
C29 H29C 0.9700 . ?
C29 H29D 0.9700 . ?
C30A H30A 0.9600 . ?
C30A H30B 0.9600 . ?
C30A H30C 0.9600 . ?
C30B H30D 0.9600 . ?
C30B H30E 0.9600 . ?
C30B H30F 0.9600 . ?
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C26 O28 C29 116.4(2) . . ?
C7 C1 C2 109.43(15) . . ?
C7 C1 C6 110.16(15) . . ?
C2 C1 C6 113.11(15) . . ?
C7 C1 C10 99.49(14) . . ?
C2 C1 C10 113.86(15) . . ?
C6 C1 C10 109.95(14) . . ?
C3 C2 C1 115.06(16) . . ?
C3 C2 H2A 108.5 . . ?
C1 C2 H2A 108.5 . . ?
C3 C2 H2B 108.5 . . ?
C1 C2 H2B 108.5 . . ?
H2A C2 H2B 107.5 . . ?
C2 C3 C4 109.30(17) . . ?
C2 C3 C13 110.42(18) . . ?
C4 C3 C13 109.78(17) . . ?
C2 C3 H3 109.1 . . ?
C4 C3 H3 109.1 . . ?
C13 C3 H3 109.1 . . ?
C3 C13 H13A 109.5 . . ?
C3 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C3 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C5 C4 C3 113.95(16) . . ?
C5 C4 H4A 108.8 . . ?
C3 C4 H4A 108.8 . . ?
C5 C4 H4B 108.8 . . ?
C3 C4 H4B 108.8 . . ?
H4A C4 H4B 107.7 . . ?
C14 C5 C6 115.02(16) . . ?
C14 C5 C4 125.70(17) . . ?
C6 C5 C4 119.26(15) . . ?
O11 C6 C5 121.37(16) . . ?
O11 C6 C1 118.23(16) . . ?
C5 C6 C1 120.39(15) . . ?
C8 C7 C26 126.67(19) . . ?
C8 C7 C1 112.49(18) . . ?
C26 C7 C1 120.71(16) . . ?
C7 C8 C9 111.66(18) . . ?
C7 C8 H8 124.2 . . ?
C9 C8 H8 124.2 . . ?
C8 C9 C10 102.96(16) . . ?
C8 C9 H9A 111.2 . . ?
C10 C9 H9A 111.2 . . ?
C8 C9 H9B 111.2 . . ?
C10 C9 H9B 111.2 . . ?
H9A C9 H9B 109.1 . . ?
C12 C10 C9 117.39(16) . . ?
C12 C10 C1 116.33(16) . . ?
C9 C10 C1 104.00(15) . . ?
C12 C10 H10 106.1 . . ?
C9 C10 H10 106.1 . . ?
C1 C10 H10 106.1 . . ?
C20 C12 C16 117.2(2) . . ?
C20 C12 C10 123.4(2) . . ?
C16 C12 C10 119.43(18) . . ?
C5 C14 C15 131.86(18) . . ?
C5 C14 H14 114.1 . . ?
C15 C14 H14 114.1 . . ?
C21 C15 C25 117.25(19) . . ?
C21 C15 C14 117.17(18) . . ?
C25 C15 C14 125.50(18) . . ?
C17 C16 C12 121.9(2) . . ?
C17 C16 H16 119.1 . . ?
C12 C16 H16 119.1 . . ?
C18 C17 C16 120.0(3) . . ?
C18 C17 H17 120.0 . . ?
C16 C17 H17 120.0 . . ?
C19 C18 C17 119.0(3) . . ?
C19 C18 H18 120.5 . . ?
C17 C18 H18 120.5 . . ?
C18 C19 C20 121.0(3) . . ?
C18 C19 H19 119.5 . . ?
C20 C19 H19 119.5 . . ?
C12 C20 C19 120.9(3) . . ?
C12 C20 H20 119.5 . . ?
C19 C20 H20 119.5 . . ?
C22 C21 C15 121.3(2) . . ?
C22 C21 H21 119.4 . . ?
C15 C21 H21 119.4 . . ?
C23 C22 C21 120.2(2) . . ?
C23 C22 H22 119.9 . . ?
C21 C22 H22 119.9 . . ?
C24 C23 C22 119.7(2) . . ?
C24 C23 H23 120.1 . . ?
C22 C23 H23 120.1 . . ?
C23 C24 C25 120.6(3) . . ?
C23 C24 H24 119.7 . . ?
C25 C24 H24 119.7 . . ?
C24 C25 C15 121.0(2) . . ?
C24 C25 H25 119.5 . . ?
C15 C25 H25 119.5 . . ?
O27 C26 O28 123.9(2) . . ?
O27 C26 C7 123.7(2) . . ?
O28 C26 C7 112.38(18) . . ?
C30B C29 C30A 124.5(6) . . ?
C30B C29 O28 120.0(5) . . ?
C30A C29 O28 114.5(4) . . ?
C30A C29 H29A 108.6 . . ?
O28 C29 H29A 108.6 . . ?
C30B C29 H29B 63.3 . . ?
C30A C29 H29B 108.6 . . ?
O28 C29 H29B 108.6 . . ?
H29A C29 H29B 107.6 . . ?
C30B C29 H29C 107.3 . . ?
C30A C29 H29C 63.5 . . ?
O28 C29 H29C 107.3 . . ?
H29A C29 H29C 142.8 . . ?
H29B C29 H29C 50.6 . . ?
C30B C29 H29D 107.3 . . ?
O28 C29 H29D 107.3 . . ?
H29A C29 H29D 71.0 . . ?
H29B C29 H29D 142.1 . . ?
H29C C29 H29D 106.9 . . ?
C29 C30A H30A 109.5 . . ?
C29 C30A H30B 109.5 . . ?
H30A C30A H30B 109.5 . . ?
C29 C30A H30C 109.5 . . ?
H30A C30A H30C 109.5 . . ?
H30B C30A H30C 109.5 . . ?
C29 C30B H30D 109.5 . . ?
C29 C30B H30E 109.5 . . ?
H30D C30B H30E 109.5 . . ?
C29 C30B H30F 109.5 . . ?
H30D C30B H30F 109.5 . . ?
H30E C30B H30F 109.5 . . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C7 C1 C2 C3 -154.76(17) . . . . ?
C6 C1 C2 C3 -31.5(2) . . . . ?
C10 C1 C2 C3 94.9(2) . . . . ?
C1 C2 C3 C4 61.3(2) . . . . ?
C1 C2 C3 C13 -177.79(18) . . . . ?
C2 C3 C4 C5 -53.1(2) . . . . ?
C13 C3 C4 C5 -174.3(2) . . . . ?
C3 C4 C5 C14 -164.09(19) . . . . ?
C3 C4 C5 C6 17.7(3) . . . . ?
C14 C5 C6 O11 12.7(3) . . . . ?
C4 C5 C6 O11 -168.93(19) . . . . ?
C14 C5 C6 C1 -166.03(17) . . . . ?
C4 C5 C6 C1 12.4(3) . . . . ?
C7 C1 C6 O11 -61.5(2) . . . . ?
C2 C1 C6 O11 175.71(18) . . . . ?
C10 C1 C6 O11 47.2(2) . . . . ?
C7 C1 C6 C5 117.24(18) . . . . ?
C2 C1 C6 C5 -5.6(2) . . . . ?
C10 C1 C6 C5 -134.09(17) . . . . ?
C2 C1 C7 C8 -100.34(19) . . . . ?
C6 C1 C7 C8 134.72(17) . . . . ?
C10 C1 C7 C8 19.3(2) . . . . ?
C2 C1 C7 C26 75.9(2) . . . . ?
C6 C1 C7 C26 -49.1(2) . . . . ?
C10 C1 C7 C26 -164.55(17) . . . . ?
C26 C7 C8 C9 -177.18(19) . . . . ?
C1 C7 C8 C9 -1.3(2) . . . . ?
C7 C8 C9 C10 -18.0(2) . . . . ?
C8 C9 C10 C12 159.01(17) . . . . ?
C8 C9 C10 C1 28.9(2) . . . . ?
C7 C1 C10 C12 -159.36(16) . . . . ?
C2 C1 C10 C12 -43.1(2) . . . . ?
C6 C1 C10 C12 85.03(19) . . . . ?
C7 C1 C10 C9 -28.63(17) . . . . ?
C2 C1 C10 C9 87.65(19) . . . . ?
C6 C1 C10 C9 -144.25(16) . . . . ?
C9 C10 C12 C20 -26.6(3) . . . . ?
C1 C10 C12 C20 97.5(2) . . . . ?
C9 C10 C12 C16 153.59(19) . . . . ?
C1 C10 C12 C16 -82.3(2) . . . . ?
C6 C5 C14 C15 175.74(19) . . . . ?
C4 C5 C14 C15 -2.5(3) . . . . ?
C5 C14 C15 C21 169.4(2) . . . . ?
C5 C14 C15 C25 -14.0(4) . . . . ?
C20 C12 C16 C17 -1.3(3) . . . . ?
C10 C12 C16 C17 178.5(2) . . . . ?
C12 C16 C17 C18 1.2(4) . . . . ?
C16 C17 C18 C19 -0.4(5) . . . . ?
C17 C18 C19 C20 -0.3(5) . . . . ?
C16 C12 C20 C19 0.6(4) . . . . ?
C10 C12 C20 C19 -179.2(2) . . . . ?
C18 C19 C20 C12 0.2(5) . . . . ?
C25 C15 C21 C22 0.6(4) . . . . ?
C14 C15 C21 C22 177.5(2) . . . . ?
C15 C21 C22 C23 -0.4(4) . . . . ?
C21 C22 C23 C24 0.4(5) . . . . ?
C22 C23 C24 C25 -0.7(5) . . . . ?
C23 C24 C25 C15 0.9(5) . . . . ?
C21 C15 C25 C24 -0.8(4) . . . . ?
C14 C15 C25 C24 -177.5(2) . . . . ?
C29 O28 C26 O27 3.0(4) . . . . ?
C29 O28 C26 C7 -176.7(3) . . . . ?
C8 C7 C26 O27 173.7(2) . . . . ?
C1 C7 C26 O27 -1.9(3) . . . . ?
C8 C7 C26 O28 -6.7(3) . . . . ?
C1 C7 C26 O28 177.68(17) . . . . ?
C26 O28 C29 C30B 87.1(7) . . . . ?
C26 O28 C29 C30A -82.0(4) . . . . ?
_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full 25.30
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max 0.403
_refine_diff_density_min -0.197
_refine_diff_density_rms 0.034