# Copyright The Royal Society of Chemistry, 1999 # CCDC Number: 188/169 data_oshima1 _publ_section_title ; Crystal and molecular structure of 6a\a ; _publ_section_abstract ; We present the crystal and molecular structure of 6a\a. ; _publ_section_comment ; The study of the titled structure was undertaken to establish its three dimensional structure. Geometries are tabulated below. All Diagrams and calculations were performed using Crystan (MacScience, Japan). ; loop_ _publ_author_name _publ_author_address 'T. Oshima' ; Osaka University ; _chemical_compound_source 'Local laboratory' _exptl_crystal_description 'Prism' _exptl_crystal_colour 'Colourless' _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.45 _exptl_crystal_size_min 0.45 _chemical_formula_sum 'C23 H20 O2 ' _chemical_formula_weight 328.41 _cell_length_a 14.601(5) _cell_length_b 9.958(2) _cell_length_c 12.509(7) _cell_angle_alpha 90.0 _cell_angle_beta 109.35(3) _cell_angle_gamma 90.0 _cell_volume 1716(1) _cell_measurement_reflns_used '22' _cell_measurement_theta_min '14.5' _cell_measurement_theta_max '17.5' _cell_formula_units_Z 4 _exptl_crystal_density_diffrn 1.271 _exptl_crystal_density_meas ? _exptl_crystal_F_000 696.0 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _exptl_absorpt_coefficient_mu 0.080 _cell_measurement_temperature '298' _diffrn_measurement_device 'Mac Science MXC3' _diffrn_measurement_method '\q/2\q' _diffrn_standards_number 3 _diffrn_standards_interval_count 100 _diffrn_standards_decay_% 'not significant' _exptl_absorpt_correction_type 'none' _diffrn_reflns_number 4185 _reflns_number_total 2904 _reflns_number_observed 2273 _reflns_observed_criterion 'refl_observed_if_I_>_2.00_sigma(I)' _diffrn_reflns_av_R_equivalents 0.113 _diffrn_reflns_theta_max 26.39 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 0 _refine_ls_structure_factor_coef F _refine_ls_R_factor_obs 0.069 _refine_ls_wR_factor_obs 0.077 _refine_ls_hydrogen_treatment 'refall' _refine_ls_number_reflns 2273 _refine_ls_number_parameters 303 _refine_ls_goodness_of_fit_obs 3.088 _refine_ls_weighting_scheme 'w = exp(10.0sin^2^\q/\l^2^)/\s^2^(Fo)' _refine_ls_shift/esd_max 0.6178 _refine_ls_shift/esd_mean 0.0218 _refine_diff_density_min -0.36 _refine_diff_density_max 0.51 _refine_ls_extinction_method 'None' _atom_type_scat_source 'International Tables (1974)' _computing_cell_refinement 'MXC(MAC Science)' _computing_data_collection 'MXC(MAC Science)' _computing_data_reduction 'Crystan' _computing_molecular_graphics 'Crystan' _computing_publication_material 'Crystan' _computing_structure_refinement 'Crystan' _computing_structure_solution 'Crystan' _symmetry_space_group_name_H-M 'P21/c ' _symmetry_cell_setting 'Monoclinic' #================================================== # ATOMIC COORDINATES AND THERMAL PARAMETERS loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_occupancy _atom_site_thermal_displace_type O1 0.07213(11) -0.06625(19) 0.23304(16) 0.0724(9) 1.000 Uij O2 0.43570(9) 0.08060(16) 0.39397(12) 0.0525(7) 1.000 Uij C1 0.15491(13) -0.04080(22) 0.29534(15) 0.0453(9) 1.000 Uij C2 0.18252(13) 0.09723(21) 0.33863(16) 0.0445(9) 1.000 Uij C3 0.27693(13) 0.12882(19) 0.38180(15) 0.0411(8) 1.000 Uij C4 0.35722(11) 0.03487(20) 0.38673(13) 0.0372(8) 1.000 Uij C5 0.33720(12) -0.11254(18) 0.37756(13) 0.0360(8) 1.000 Uij C6 0.22903(13) -0.14757(19) 0.32931(13) 0.0391(8) 1.000 Uij C7 0.10212(17) 0.19462(31) 0.32802(30) 0.073(1) 1.000 Uij C8 0.40670(17) -0.19313(25) 0.33682(17) 0.053(1) 1.000 Uij C9 0.28606(11) -0.17326(18) 0.45522(13) 0.0341(7) 1.000 Uij C10 0.26724(12) -0.09305(18) 0.54832(13) 0.0351(7) 1.000 Uij C11 0.34219(12) -0.01251(18) 0.61801(14) 0.0378(8) 1.000 Uij C12 0.32920(16) 0.05595(21) 0.70867(16) 0.051(1) 1.000 Uij C13 0.24401(19) 0.04421(25) 0.73074(19) 0.063(1) 1.000 Uij C14 0.17026(16) -0.03831(24) 0.66307(19) 0.057(1) 1.000 Uij C15 0.18145(13) -0.10921(19) 0.57271(15) 0.0419(8) 1.000 Uij C16 0.09878(15) -0.20286(27) 0.50918(22) 0.062(1) 1.000 Uij C17 0.11912(18) -0.32776(28) 0.44996(22) 0.063(1) 1.000 Uij C18 0.21918(15) -0.38968(21) 0.49728(16) 0.050(1) 1.000 Uij C19 0.2325(2) -0.5175(2) 0.5443(2) 0.067(1) 1.000 Uij C20 0.3235(3) -0.5755(2) 0.5854(2) 0.078(2) 1.000 Uij C21 0.4045(2) -0.5045(2) 0.5814(2) 0.064(1) 1.000 Uij C22 0.39322(16) -0.37395(21) 0.53756(15) 0.049(1) 1.000 Uij C23 0.30069(14) -0.31835(19) 0.49319(13) 0.0409(8) 1.000 Uij H3 0.3008(13) 0.2158(20) 0.4074(15) 0.030(5) 1.000 Uiso H6 0.2093(18) -0.2320(26) 0.2806(20) 0.061(7) 1.000 Uiso H7A 0.064(3) 0.161(4) 0.371(3) 0.10(1) 1.000 Uiso H7B 0.116(3) 0.275(4) 0.361(3) 0.11(1) 1.000 Uiso H7C 0.041(4) 0.193(6) 0.257(4) 0.20(2) 1.000 Uiso H8A 0.3968(17) -0.2833(27) 0.3367(19) 0.055(7) 1.000 Uiso H8B 0.4278(18) -0.1574(26) 0.2717(21) 0.067(7) 1.000 Uiso H8C 0.478(2) -0.190(3) 0.392(2) 0.073(8) 1.000 Uiso H11 0.4033(14) -0.0038(22) 0.5982(17) 0.042(5) 1.000 Uiso H12 0.3874(17) 0.1129(25) 0.7545(19) 0.059(7) 1.000 Uiso H13 0.225(2) 0.090(3) 0.786(2) 0.079(9) 1.000 Uiso H14 0.1128(15) -0.0450(22) 0.6803(17) 0.042(5) 1.000 Uiso H16A 0.056(2) -0.230(3) 0.557(2) 0.076(8) 1.000 Uiso H16B 0.033(2) -0.136(3) 0.456(3) 0.10(1) 1.000 Uiso H17A 0.0705(19) -0.3955(28) 0.4572(22) 0.074(8) 1.000 Uiso H17B 0.116(2) -0.313(3) 0.381(3) 0.09(1) 1.000 Uiso H19 0.1785(17) -0.5630(24) 0.5542(19) 0.052(6) 1.000 Uiso H20 0.3305(19) -0.6647(29) 0.6127(22) 0.071(8) 1.000 Uiso H21 0.4806(19) -0.5473(28) 0.6102(21) 0.073(8) 1.000 Uiso H22 0.4560(16) -0.3351(23) 0.5361(18) 0.048(6) 1.000 Uiso loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 O1 0.0430(8) 0.0678(12) 0.0834(12) -.0063(8) -.0200(8) 0.0046(9) O2 0.0361(6) 0.0543(9) 0.0603(8) -.0021(6) 0.0133(6) 0.0047(7) C1 0.0341(8) 0.0534(11) 0.0400(8) -.0046(8) 0.0019(7) 0.0078(8) C2 0.0368(8) 0.0426(10) 0.0462(9) 0.0045(8) 0.0067(7) 0.0100(8) C3 0.0405(9) 0.0331(10) 0.0422(9) -.0016(7) 0.0071(7) 0.0064(7) C4 0.0310(7) 0.0444(10) 0.0313(7) -.0001(7) 0.0075(6) 0.0044(7) C5 0.0360(8) 0.0388(9) 0.0281(7) 0.0022(7) 0.0076(6) 0.0036(7) C6 0.0410(9) 0.0392(10) 0.0300(7) -.0017(7) 0.0040(6) -.0014(7) C7 0.037(1) 0.059(2) 0.111(2) 0.011(1) 0.013(1) -0.002(2) C8 0.062(1) 0.049(1) 0.044(1) 0.009(1) 0.029(1) 0.003(1) C9 0.0316(7) 0.0358(9) 0.0293(7) 0.0001(7) 0.0046(6) 0.0006(6) C10 0.0358(7) 0.0332(9) 0.0316(7) 0.0013(7) 0.0096(6) 0.0039(7) C11 0.0379(8) 0.0353(9) 0.0339(8) -.0013(7) 0.0072(6) 0.0014(7) C12 0.060(1) 0.043(1) 0.040(1) 0.002(1) 0.010(1) -0.006(1) C13 0.082(2) 0.051(1) 0.051(1) 0.001(1) 0.035(1) -0.010(1) C14 0.057(1) 0.055(1) 0.058(1) 0.008(1) 0.035(1) 0.004(1) C15 0.0377(8) 0.0402(10) 0.0426(8) 0.0024(8) 0.0127(6) 0.0072(8) C16 0.038(1) 0.068(2) 0.072(1) -0.010(1) 0.016(1) -0.008(1) C17 0.054(1) 0.064(2) 0.061(1) -0.023(1) 0.013(1) -0.006(1) C18 0.062(1) 0.038(1) 0.042(1) -0.008(1) 0.016(1) -0.004(1) C19 0.101(2) 0.040(1) 0.052(1) -0.014(1) 0.032(1) -0.002(1) C20 0.142(3) 0.033(1) 0.049(1) 0.009(1) 0.035(1) 0.003(1) C21 0.091(2) 0.047(1) 0.044(1) 0.025(1) 0.016(1) 0.004(1) C22 0.059(1) 0.043(1) 0.037(1) 0.009(1) 0.013(1) 0.000(1) C23 0.055(1) 0.034(1) 0.027(1) 0.002(1) 0.010(1) -0.001(1) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C1 1.228(3) . . yes O2 C4 1.208(3) . . yes C1 C2 1.484(3) . . yes C1 C6 1.476(3) . . yes C2 C3 1.341(3) . . yes C2 C7 1.494(4) . . yes C3 C4 1.485(3) . . yes C4 C5 1.494(3) . . yes C5 C6 1.533(3) . . yes C5 C8 1.509(3) . . yes C5 C9 1.532(3) . . yes C6 C9 1.540(3) . . yes C9 C10 1.511(3) . . yes C9 C23 1.514(3) . . yes C10 C11 1.403(3) . . yes C10 C15 1.393(3) . . yes C11 C12 1.389(3) . . yes C12 C13 1.365(4) . . yes C13 C14 1.396(4) . . yes C14 C15 1.388(3) . . yes C15 C16 1.524(4) . . yes C16 C17 1.527(4) . . yes C17 C18 1.514(4) . . yes C18 C19 1.388(4) . . yes C18 C23 1.401(3) . . yes C19 C20 1.382(5) . . yes C20 C21 1.393(5) . . yes C21 C22 1.399(4) . . yes C22 C23 1.394(3) . . yes C3 H3 0.95(2) . . ? C6 H6 1.02(3) . . ? C7 H7A 0.96(4) . . ? C7 H7B 0.90(4) . . ? C7 H7C 1.03(6) . . ? C8 H8A 0.91(3) . . ? C8 H8B 1.03(3) . . ? C8 H8C 1.05(3) . . ? C11 H11 1.01(2) . . ? C12 H12 1.02(3) . . ? C13 H13 0.94(3) . . ? C14 H14 0.93(3) . . ? C16 H16A 1.04(3) . . ? C16 H16B 1.18(4) . . ? C17 H17A 1.00(3) . . ? C17 H17B 0.86(4) . . ? C19 H19 0.95(3) . . ? C20 H20 0.95(3) . . ? C21 H21 1.13(3) . . ? C22 H22 1.00(3) . . ? 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 C1 C2 120.9(2) . . . yes O1 C1 C6 120.5(2) . . . yes C2 C1 C6 118.5(2) . . . yes C1 C2 C3 118.9(2) . . . yes C1 C2 C7 117.3(2) . . . yes C3 C2 C7 123.8(3) . . . yes C2 C3 C4 124.1(2) . . . yes O2 C4 C3 118.8(2) . . . yes O2 C4 C5 122.2(2) . . . yes C3 C4 C5 119.0(2) . . . yes C4 C5 C6 113.8(2) . . . yes C4 C5 C8 114.4(2) . . . yes C4 C5 C9 117.6(2) . . . yes C6 C5 C8 117.8(2) . . . yes C6 C5 C9 60.3(2) . . . yes C8 C5 C9 121.9(2) . . . yes C1 C6 C5 120.7(2) . . . yes C1 C6 C9 120.7(2) . . . yes C5 C6 C9 59.8(2) . . . yes C5 C9 C6 59.9(2) . . . yes C5 C9 C10 122.1(2) . . . yes C5 C9 C23 121.8(2) . . . yes C6 C9 C10 121.7(2) . . . yes C6 C9 C23 116.8(2) . . . yes C10 C9 C23 107.8(2) . . . yes C9 C10 C11 118.5(2) . . . yes C9 C10 C15 120.9(2) . . . yes C11 C10 C15 120.2(2) . . . yes C10 C11 C12 119.9(2) . . . yes C11 C12 C13 120.2(2) . . . yes C12 C13 C14 119.9(3) . . . yes C13 C14 C15 121.2(3) . . . yes C10 C15 C14 118.5(2) . . . yes C10 C15 C16 124.8(2) . . . yes C14 C15 C16 116.7(2) . . . yes C15 C16 C17 120.3(2) . . . yes C16 C17 C18 117.4(3) . . . yes C17 C18 C19 121.4(3) . . . yes C17 C18 C23 120.0(2) . . . yes C19 C18 C23 118.6(3) . . . yes C18 C19 C20 121.5(3) . . . yes C19 C20 C21 119.9(3) . . . yes C20 C21 C22 119.6(3) . . . yes C21 C22 C23 119.8(3) . . . yes C9 C23 C18 117.5(2) . . . yes C9 C23 C22 121.4(2) . . . yes C18 C23 C22 120.5(2) . . . yes C2 C3 H3 124.4(12) . . . ? C4 C3 H3 111.3(12) . . . ? C1 C6 H6 112.7(14) . . . ? C5 C6 H6 118.1(14) . . . ? C9 C6 H6 115.1(14) . . . ? C2 C7 H7A 108.2(23) . . . ? C2 C7 H7B 119.2(24) . . . ? C2 C7 H7C 119.8(31) . . . ? H7A C7 H7B 98.4(33) . . . ? H7A C7 H7C 88.6(36) . . . ? H7B C7 H7C 114.5(40) . . . ? C5 C8 H8A 113.6(16) . . . ? C5 C8 H8B 119.8(15) . . . ? C5 C8 H8C 113.4(15) . . . ? H8A C8 H8B 115.5(21) . . . ? H8A C8 H8C 98.7(22) . . . ? H8B C8 H8C 91.2(21) . . . ? C10 C11 H11 118.0(12) . . . ? C12 C11 H11 122.1(12) . . . ? C11 C12 H12 114.6(14) . . . ? C13 C12 H12 125.2(14) . . . ? C12 C13 H13 128.2(17) . . . ? C14 C13 H13 111.8(17) . . . ? C13 C14 H14 118.2(13) . . . ? C15 C14 H14 120.5(13) . . . ? C15 C16 H16A 112.4(16) . . . ? C15 C16 H16B 108.0(16) . . . ? C17 C16 H16A 108.9(16) . . . ? C17 C16 H16B 116.2(16) . . . ? H16A C16 H16B 86.0(22) . . . ? C16 C17 H17A 104.3(16) . . . ? C16 C17 H17B 112.8(23) . . . ? C18 C17 H17A 108.1(16) . . . ? C18 C17 H17B 101.0(22) . . . ? H17A C17 H17B 113.6(27) . . . ? C18 C19 H19 119.1(15) . . . ? C20 C19 H19 119.2(15) . . . ? C19 C20 H20 120.2(17) . . . ? C21 C20 H20 119.9(17) . . . ? C20 C21 H21 123.6(14) . . . ? C22 C21 H21 116.7(14) . . . ? C21 C22 H22 112.1(13) . . . ? C23 C22 H22 127.7(13) . . . ? 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 O1 C1 C2 C3 -163.5(3) . . . . yes O1 C1 C2 C7 14.7(3) . . . . yes O1 C1 C6 C5 162.6(3) . . . . yes O1 C1 C6 C9 -126.5(3) . . . . yes C6 C1 C2 C3 16.9(2) . . . . yes C2 C1 C6 C5 -17.8(2) . . . . yes C6 C1 C2 C7 -164.9(3) . . . . yes C2 C1 C6 C9 53.1(2) . . . . yes C1 C2 C3 C4 1.7(2) . . . . yes C7 C2 C3 C4 -176.4(4) . . . . yes C2 C3 C4 O2 157.7(3) . . . . yes C2 C3 C4 C5 -19.6(2) . . . . yes O2 C4 C5 C6 -160.1(3) . . . . yes O2 C4 C5 C8 -20.7(2) . . . . yes O2 C4 C5 C9 132.2(3) . . . . yes C3 C4 C5 C6 17.2(2) . . . . yes C3 C4 C5 C8 156.6(3) . . . . yes C3 C4 C5 C9 -50.5(2) . . . . yes C4 C5 C6 C1 0.6(2) . . . . yes C4 C5 C6 C9 -109.3(2) . . . . yes C4 C5 C9 C6 103.1(2) . . . . yes C4 C5 C9 C10 -7.6(2) . . . . yes C4 C5 C9 C23 -152.2(3) . . . . yes C8 C5 C6 C1 -137.3(3) . . . . yes C8 C5 C6 C9 112.7(2) . . . . yes C9 C5 C6 C1 110.0(2) . . . . yes C6 C5 C9 C6 0.0(2) . . . . yes C9 C5 C6 C9 0.0(1) . . . . yes C6 C5 C9 C10 -110.7(2) . . . . yes C6 C5 C9 C23 104.7(2) . . . . yes C8 C5 C9 C6 -106.1(2) . . . . yes C8 C5 C9 C10 143.1(3) . . . . yes C8 C5 C9 C23 -1.4(2) . . . . yes C1 C6 C9 C5 -110.0(2) . . . . yes C1 C6 C9 C10 1.3(2) . . . . yes C1 C6 C9 C23 137.0(3) . . . . yes C5 C6 C9 C5 0.0(2) . . . . yes C5 C6 C9 C10 111.3(2) . . . . yes C5 C6 C9 C23 -113.0(2) . . . . yes C5 C9 C10 C11 -44.7(2) . . . . yes C5 C9 C10 C15 142.1(3) . . . . yes C5 C9 C23 C18 -140.0(3) . . . . yes C5 C9 C23 C22 48.8(2) . . . . yes C6 C9 C10 C11 -116.7(3) . . . . yes C6 C9 C10 C15 70.1(2) . . . . yes C6 C9 C23 C18 -70.4(2) . . . . yes C6 C9 C23 C22 118.4(3) . . . . yes C23 C9 C10 C11 104.2(2) . . . . yes C23 C9 C10 C15 -69.0(2) . . . . yes C10 C9 C23 C18 71.0(2) . . . . yes C10 C9 C23 C22 -100.2(3) . . . . yes C9 C10 C11 C12 -176.0(3) . . . . yes C9 C10 C15 C14 176.6(3) . . . . yes C9 C10 C15 C16 -1.6(2) . . . . yes C15 C10 C11 C12 -2.8(2) . . . . yes C11 C10 C15 C14 3.5(2) . . . . yes C11 C10 C15 C16 -174.7(3) . . . . yes C10 C11 C12 C13 0.5(2) . . . . yes C11 C12 C13 C14 0.9(3) . . . . yes C12 C13 C14 C15 -0.2(3) . . . . yes C13 C14 C15 C10 -2.0(2) . . . . yes C13 C14 C15 C16 176.3(4) . . . . yes C10 C15 C16 C17 26.8(3) . . . . yes C14 C15 C16 C17 -151.5(3) . . . . yes C15 C16 C17 C18 27.3(3) . . . . yes C16 C17 C18 C19 115.4(4) . . . . yes C16 C17 C18 C23 -65.3(3) . . . . yes C17 C18 C19 C20 178.6(4) . . . . yes C17 C18 C23 C9 8.1(2) . . . . yes C17 C18 C23 C22 179.4(3) . . . . yes C19 C18 C23 C9 -172.5(3) . . . . yes C23 C18 C19 C20 -0.8(3) . . . . yes C19 C18 C23 C22 -1.3(3) . . . . yes C18 C19 C20 C21 0.8(3) . . . . yes C19 C20 C21 C22 1.2(3) . . . . yes C20 C21 C22 C23 -3.1(3) . . . . yes C21 C22 C23 C9 174.1(3) . . . . yes C21 C22 C23 C18 3.2(2) . . . . yes O1 C1 C6 H6 15.0(16) . . . . ? C2 C1 C6 H6 -165.3(16) . . . . ? C1 C2 C3 H3 176.4(14) . . . . ? C1 C2 C7 H7A 61.6(24) . . . . ? C1 C2 C7 H7B 172.7(28) . . . . ? C1 C2 C7 H7C -37.4(34) . . . . ? C7 C2 C3 H3 -1.7(14) . . . . ? C3 C2 C7 H7A -120.2(24) . . . . ? C3 C2 C7 H7B -9.2(28) . . . . ? C3 C2 C7 H7C 140.7(34) . . . . ? H3 C3 C4 O2 -17.6(13) . . . . ? H3 C3 C4 C5 165.0(13) . . . . ? C4 C5 C6 H6 146.5(16) . . . . ? C4 C5 C8 H8A 175.6(18) . . . . ? C4 C5 C8 H8B -42.0(17) . . . . ? C4 C5 C8 H8C 63.9(17) . . . . ? C8 C5 C6 H6 8.6(16) . . . . ? C6 C5 C8 H8A -46.7(17) . . . . ? C6 C5 C8 H8B 95.7(17) . . . . ? C6 C5 C8 H8C -158.4(17) . . . . ? C9 C5 C6 H6 -104.2(16) . . . . ? C9 C5 C8 H8A 23.9(17) . . . . ? C9 C5 C8 H8B 166.4(17) . . . . ? C9 C5 C8 H8C -87.8(17) . . . . ? H6 C6 C9 C5 109.3(16) . . . . ? H6 C6 C9 C10 -139.4(16) . . . . ? H6 C6 C9 C23 -3.7(16) . . . . ? C9 C10 C11 H11 6.2(14) . . . . ? C15 C10 C11 H11 179.4(14) . . . . ? C10 C11 C12 H12 -179.5(15) . . . . ? H11 C11 C12 C13 178.2(14) . . . . ? H11 C11 C12 H12 -1.8(21) . . . . ? C11 C12 C13 H13 -174.9(22) . . . . ? H12 C12 C13 C14 -179.0(17) . . . . ? H12 C12 C13 H13 5.1(27) . . . . ? C12 C13 C14 H14 179.6(15) . . . . ? H13 C13 C14 C15 176.3(19) . . . . ? H13 C13 C14 H14 -3.9(24) . . . . ? H14 C14 C15 C10 178.2(15) . . . . ? H14 C14 C15 C16 -3.4(15) . . . . ? C10 C15 C16 H16A 157.0(17) . . . . ? C10 C15 C16 H16B -109.9(17) . . . . ? C14 C15 C16 H16A -21.2(17) . . . . ? C14 C15 C16 H16B 71.9(17) . . . . ? C15 C16 C17 H17A 146.9(17) . . . . ? C15 C16 C17 H17B -89.4(24) . . . . ? H16A C16 C17 C18 -104.5(17) . . . . ? H16A C16 C17 H17A 15.1(23) . . . . ? H16A C16 C17 H17B 138.8(29) . . . . ? H16B C16 C17 C18 160.6(18) . . . . ? H16B C16 C17 H17A -79.9(24) . . . . ? H16B C16 C17 H17B 43.8(29) . . . . ? H17A C17 C18 C19 -2.1(17) . . . . ? H17A C17 C18 C23 177.2(17) . . . . ? H17B C17 C18 C19 -121.6(22) . . . . ? H17B C17 C18 C23 57.7(22) . . . . ? C17 C18 C19 H19 -6.8(16) . . . . ? C23 C18 C19 H19 173.8(17) . . . . ? C18 C19 C20 H20 -176.0(20) . . . . ? H19 C19 C20 C21 -173.8(17) . . . . ? H19 C19 C20 H20 9.4(25) . . . . ? C19 C20 C21 H21 -177.5(17) . . . . ? H20 C20 C21 C22 178.0(20) . . . . ? H20 C20 C21 H21 -0.6(25) . . . . ? C20 C21 C22 H22 -177.5(14) . . . . ? H21 C21 C22 C23 175.6(16) . . . . ? H21 C21 C22 H22 1.2(21) . . . . ? H22 C22 C23 C9 -12.5(16) . . . . ? H22 C22 C23 C18 176.6(17) . . . . ? #======END data_oshima2 _publ_section_title ; Crystal and molecular structure of 6a\b ; _publ_section_abstract ; We present the crystal and molecular structure of 6a\b. ; _publ_section_comment ; The study of the titled structure was undertaken to establish its three dimensional structure. Geometries are tabulated below. All Diagrams and calculations were performed using Crystan (MacScience, Japan). ; loop_ _publ_author_name _publ_author_address 'T. Oshima' ; Osaka University ; _chemical_compound_source 'Local laboratory' _exptl_crystal_description 'Plate' _exptl_crystal_colour 'Colourless' _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.45 _exptl_crystal_size_min 0.20 _chemical_formula_sum 'C23 H20 O2 ' _chemical_formula_weight 328.41 _cell_length_a 15.689(5) _cell_length_b 25.081(8) _cell_length_c 8.880(3) _cell_angle_alpha 90.0 _cell_angle_beta 90.0 _cell_angle_gamma 90.0 _cell_volume 3494(2) _cell_measurement_reflns_used '22' _cell_measurement_theta_min '10.7' _cell_measurement_theta_max '12.1' _cell_formula_units_Z 8 _exptl_crystal_density_diffrn 1.249 _exptl_crystal_density_meas ? _exptl_crystal_F_000 1392 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _exptl_absorpt_coefficient_mu 0.078 _cell_measurement_temperature '298' _diffrn_measurement_device 'Mac Science MXC3' _diffrn_measurement_method '\q/2\q' _diffrn_standards_number 3 _diffrn_standards_interval_count 100 _diffrn_standards_decay_% 'not significant' _exptl_absorpt_correction_type 'empirical, \y scans' _exptl_absorpt_correction_T_min .658 _exptl_absorpt_correction_T_max .998 _diffrn_reflns_number 2983 _reflns_number_total 1629 _reflns_number_observed 1629 _reflns_observed_criterion 'refl_observed_if_I_>_0.00_sigma(I)' _diffrn_reflns_av_R_equivalents 0.019 _diffrn_reflns_theta_max 23.99 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 0 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 29 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 9 _refine_ls_structure_factor_coef F^2^ _refine_ls_R_factor_obs 0.095 _refine_ls_wR_factor_obs 0.097 _refine_ls_hydrogen_treatment 'refU' _refine_ls_number_reflns 1692 _refine_ls_number_parameters 244 _refine_ls_goodness_of_fit_obs 1.658 _refine_ls_weighting_scheme ;w = 1/(\s^2^(Fo) + 0.01Fo^2^) ; _refine_ls_shift/esd_max 0.1475 _refine_ls_shift/esd_mean 0.0399 _refine_diff_density_min -0.30 _refine_diff_density_max 0.25 _refine_ls_extinction_method 'None' _atom_type_scat_source 'International Tables (1974)' _computing_cell_refinement 'MXC(MAC Science)' _computing_data_collection 'MXC(MAC Science)' _computing_data_reduction 'Crystan' _computing_molecular_graphics 'Crystan' _computing_publication_material 'Crystan' _computing_structure_refinement 'Crystan' _computing_structure_solution 'Crystan' _symmetry_space_group_name_H-M 'P c c n ' _symmetry_cell_setting 'Orthorhombic' #================================================== # ATOMIC COORDINATES AND THERMAL PARAMETERS loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_occupancy _atom_site_thermal_displace_type O1 -0.6195(4) -0.7424(3) -0.1263(7) 0.082(4) 1.000 Uij O2 -0.6637(4) -0.5437(2) -0.3117(7) 0.080(4) 1.000 Uij C1 -0.6154(6) -0.6951(3) -0.1577(9) 0.060(5) 1.000 Uij C2 -0.6582(5) -0.6544(4) -0.0631(9) 0.060(5) 1.000 Uij C3 -0.6658(6) -0.6046(3) -0.1127(9) 0.058(5) 1.000 Uij C4 -0.6380(5) -0.5861(3) -0.2640(9) 0.058(5) 1.000 Uij C5 -0.5815(5) -0.6210(3) -0.3540(9) 0.052(5) 1.000 Uij C6 -0.5698(5) -0.6772(3) -0.2957(9) 0.058(5) 1.000 Uij C7 -0.6917(8) -0.6728(5) 0.0853(11) 0.086(8) 1.000 Uij C8 -0.5849(6) -0.6118(4) -0.5240(10) 0.070(6) 1.000 Uij C9 -0.4955(5) -0.6384(3) -0.2856(8) 0.049(5) 1.000 Uij C10 -0.4666(5) -0.6164(3) -0.1344(9) 0.053(5) 1.000 Uij C11 -0.4588(6) -0.6488(3) -0.0078(10) 0.063(5) 1.000 Uij C12 -0.4310(6) -0.6281(4) 0.1268(11) 0.077(7) 1.000 Uij C13 -0.4087(7) -0.5748(4) 0.1356(11) 0.078(7) 1.000 Uij C14 -0.4137(6) -0.5436(4) 0.0086(11) 0.070(6) 1.000 Uij C15 -0.4411(5) -0.5639(3) -0.1285(9) 0.057(5) 1.000 Uij C16 -0.4397(6) -0.5301(3) -0.2687(10) 0.067(6) 1.000 Uij C17 -0.3694(7) -0.5476(4) -0.3765(11) 0.078(7) 1.000 Uij C18 -0.3655(6) -0.6055(3) -0.4309(10) 0.060(6) 1.000 Uij C19 -0.2981(6) -0.6165(4) -0.5282(11) 0.075(7) 1.000 Uij C20 -0.2847(7) -0.6657(5) -0.5849(13) 0.092(8) 1.000 Uij C21 -0.3380(7) -0.7076(4) -0.5448(14) 0.096(8) 1.000 Uij C22 -0.4043(6) -0.6970(4) -0.4477(13) 0.082(7) 1.000 Uij C23 -0.4207(5) -0.6464(3) -0.3911(10) 0.060(5) 1.000 Uij H7A -0.719(6) -0.646(4) 0.144(11) 0.07(3) 1.000 Uiso H7B -0.645(6) -0.687(4) 0.144(11) 0.14(5) 1.000 Uiso H7C -0.732(8) -0.701(4) 0.067(12) 0.16(6) 1.000 Uiso H3 -0.689(6) -0.579(4) -0.043(11) 0.09(3) 1.000 Uiso H22 -0.440(9) -0.726(4) -0.417(14) 0.07(3) 1.000 Uiso H21 -0.329(6) -0.743(3) -0.586(10) 0.10(3) 1.000 Uiso H20 -0.236(7) -0.672(4) -0.649(12) 0.11(4) 1.000 Uiso H19 -0.261(7) -0.588(4) -0.559(12) 0.08(3) 1.000 Uiso H16A -0.43195 -0.49326 -0.24287 0.07(3) 1.000 Uiso H16B -0.49355 -0.53416 -0.31887 0.06(2) 1.000 Uiso H17A -0.316(9) -0.540(6) -0.327(16) 0.15(5) 1.000 Uiso H17B -0.374(5) -0.526(4) -0.466(10) 0.10(7) 1.000 Uiso H11 -0.472(6) -0.686(4) -0.015(10) 0.05(2) 1.000 Uiso H12 -0.427(6) -0.650(3) 0.215(9) 0.12(4) 1.000 Uiso H13 -0.39027 -0.56040 0.23026 0.1(1) 1.000 Uiso H14 -0.39686 -0.50691 0.01594 0.06(2) 1.000 Uiso H8A -0.548(7) -0.635(4) -0.579(11) 0.08(3) 1.000 Uiso H8B -0.570(9) -0.576(5) -0.548(15) 0.15(5) 1.000 Uiso H8C -0.643(6) -0.618(5) -0.555(12) 0.10(4) 1.000 Uiso H6 -0.54605 -0.70400 -0.36042 0.10(3) 1.000 Uiso loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 O1 0.113(5) 0.068(4) 0.064(4) -0.009(4) 0.009(4) 0.006(3) O2 0.098(5) 0.077(4) 0.064(4) 0.021(4) 0.003(4) 0.013(4) C1 0.069(6) 0.068(6) 0.043(5) -0.003(5) -0.006(5) 0.007(5) C2 0.061(5) 0.080(6) 0.041(5) -0.006(5) 0.000(4) 0.007(5) C3 0.065(6) 0.067(6) 0.042(5) -0.002(5) 0.001(4) -0.005(5) C4 0.061(5) 0.064(5) 0.048(5) -0.001(5) -0.006(5) 0.004(5) C5 0.057(5) 0.061(5) 0.037(5) 0.001(4) -0.001(4) 0.005(4) C6 0.067(6) 0.066(5) 0.041(5) 0.008(5) 0.003(4) -0.003(4) C7 0.092(8) 0.114(9) 0.053(6) 0.011(8) 0.028(6) 0.011(6) C8 0.070(7) 0.098(8) 0.042(6) 0.011(6) 0.001(5) -0.001(5) C9 0.060(5) 0.051(4) 0.036(5) 0.000(4) -0.002(4) -0.004(4) C10 0.056(5) 0.062(5) 0.041(5) 0.007(4) 0.002(4) 0.000(4) C11 0.065(6) 0.072(6) 0.051(6) 0.001(5) -0.002(5) 0.008(5) C12 0.082(7) 0.112(8) 0.036(5) 0.010(6) -0.007(5) 0.007(6) C13 0.084(7) 0.103(8) 0.047(6) 0.013(6) -0.009(5) -0.014(6) C14 0.078(6) 0.073(6) 0.061(6) -0.004(5) 0.001(5) -0.019(5) C15 0.064(5) 0.060(5) 0.046(5) 0.004(4) -0.003(5) -0.007(5) C16 0.072(6) 0.065(6) 0.065(6) -0.006(5) -0.003(6) 0.002(5) C17 0.092(8) 0.082(7) 0.062(6) -0.016(6) 0.004(6) 0.013(5) C18 0.062(6) 0.070(6) 0.048(5) -0.001(5) -0.009(5) 0.006(4) C19 0.053(6) 0.110(8) 0.063(7) 0.004(6) 0.006(5) 0.018(6) C20 0.062(7) 0.118(10) 0.096(9) 0.020(7) 0.012(6) -0.003(7) C21 0.074(7) 0.096(8) 0.118(10) 0.021(6) 0.013(7) -0.034(7) C22 0.063(6) 0.080(7) 0.102(8) 0.010(6) 0.009(6) -0.003(6) C23 0.055(5) 0.072(6) 0.053(6) 0.004(5) -0.005(4) 0.001(5) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C1 1.219(11) . . yes O2 C4 1.213(11) . . yes C1 C2 1.484(13) . . yes C1 C6 1.488(12) . . yes C2 C3 1.329(13) . . yes C2 C7 1.491(14) . . yes C3 C4 1.487(12) . . yes C4 C5 1.481(12) . . yes C5 C6 1.513(12) . . yes C5 C8 1.528(12) . . yes C5 C9 1.543(12) . . yes C6 C9 1.520(12) . . yes C9 C10 1.520(11) . . yes C9 C23 1.515(12) . . yes C10 C11 1.393(12) . . yes C10 C15 1.377(12) . . yes C11 C12 1.374(14) . . yes C12 C13 1.384(16) . . yes C13 C14 1.374(14) . . yes C14 C15 1.389(13) . . yes C15 C16 1.506(13) . . yes C16 C17 1.526(14) . . yes C17 C18 1.530(13) . . yes C18 C19 1.394(14) . . yes C18 C23 1.388(13) . . yes C19 C20 1.351(17) . . yes C20 C21 1.389(17) . . yes C21 C22 1.377(16) . . yes C22 C23 1.389(14) . . yes C3 H3 0.96(10) . . ? C6 H6 0.959(9) . . ? C7 H7A 0.96(10) . . ? C7 H7B 0.96(10) . . ? C7 H7C 0.96(12) . . ? C8 H8A 0.96(11) . . ? C8 H8B 0.96(14) . . ? C8 H8C 0.96(11) . . ? C11 H11 0.96(10) . . ? C12 H12 0.96(8) . . ? C13 H13 0.960(10) . . ? C14 H14 0.960(10) . . ? C16 H16A 0.959(9) . . ? C16 H16B 0.960(9) . . ? C17 H17A 0.96(15) . . ? C17 H17B 0.96(9) . . ? C19 H19 0.96(11) . . ? C20 H20 0.96(11) . . ? C21 H21 0.96(9) . . ? C22 H22 0.96(13) . . ? 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 C1 C2 121.0(8) . . . yes O1 C1 C6 120.5(8) . . . yes C2 C1 C6 118.4(8) . . . yes C1 C2 C3 119.9(8) . . . yes C1 C2 C7 116.6(9) . . . yes C3 C2 C7 123.5(9) . . . yes C2 C3 C4 124.6(8) . . . yes O2 C4 C3 119.5(8) . . . yes O2 C4 C5 121.9(8) . . . yes C3 C4 C5 118.6(8) . . . yes C4 C5 C6 116.1(7) . . . yes C4 C5 C8 115.0(8) . . . yes C4 C5 C9 118.6(7) . . . yes C6 C5 C8 118.9(7) . . . yes C6 C5 C9 59.7(5) . . . yes C8 C5 C9 117.5(7) . . . yes C1 C6 C5 120.3(7) . . . yes C1 C6 C9 120.9(7) . . . yes C5 C6 C9 61.1(6) . . . yes C5 C9 C6 59.2(6) . . . yes C5 C9 C10 120.3(7) . . . yes C5 C9 C23 118.1(7) . . . yes C6 C9 C10 120.9(7) . . . yes C6 C9 C23 118.2(7) . . . yes C10 C9 C23 111.3(7) . . . yes C9 C10 C11 121.8(7) . . . yes C9 C10 C15 117.9(7) . . . yes C11 C10 C15 120.1(8) . . . yes C10 C11 C12 120.6(9) . . . yes C11 C12 C13 119.6(10) . . . yes C12 C13 C14 119.3(10) . . . yes C13 C14 C15 121.9(9) . . . yes C10 C15 C14 118.3(8) . . . yes C10 C15 C16 120.8(8) . . . yes C14 C15 C16 120.9(8) . . . yes C15 C16 C17 111.5(8) . . . yes C16 C17 C18 120.1(9) . . . yes C17 C18 C19 114.4(9) . . . yes C17 C18 C23 126.5(9) . . . yes C19 C18 C23 119.0(9) . . . yes C18 C19 C20 122.0(10) . . . yes C19 C20 C21 120.2(11) . . . yes C20 C21 C22 117.9(11) . . . yes C21 C22 C23 122.9(10) . . . yes C9 C23 C18 122.9(8) . . . yes C9 C23 C22 119.2(8) . . . yes C18 C23 C22 117.9(9) . . . yes C2 C3 H3 116.7(59) . . . ? C4 C3 H3 118.7(59) . . . ? C1 C6 H6 117.9(8) . . . ? C5 C6 H6 119.7(8) . . . ? C9 C6 H6 100.8(7) . . . ? C2 C7 H7A 114.8(57) . . . ? C2 C7 H7B 108.8(60) . . . ? C2 C7 H7C 108.2(64) . . . ? H7A C7 H7B 107.9(82) . . . ? H7A C7 H7C 108.0(87) . . . ? H7B C7 H7C 109.0(87) . . . ? C5 C8 H8A 112.8(61) . . . ? C5 C8 H8B 110.6(78) . . . ? C5 C8 H8C 106.6(64) . . . ? H8A C8 H8B 108.9(100) . . . ? H8A C8 H8C 108.8(96) . . . ? H8B C8 H8C 109.0(115) . . . ? C10 C11 H11 119.5(56) . . . ? C12 C11 H11 119.8(56) . . . ? C11 C12 H12 120.5(49) . . . ? C13 C12 H12 119.9(48) . . . ? C12 C13 H13 119.3(10) . . . ? C14 C13 H13 121.4(11) . . . ? C13 C14 H14 118.4(10) . . . ? C15 C14 H14 119.7(9) . . . ? C15 C16 H16A 110.3(9) . . . ? C15 C16 H16B 108.1(8) . . . ? C17 C16 H16A 109.6(9) . . . ? C17 C16 H16B 108.3(9) . . . ? H16A C16 H16B 109.0(9) . . . ? C16 C17 H17A 106.3(88) . . . ? C16 C17 H17B 107.7(53) . . . ? C18 C17 H17A 107.5(87) . . . ? C18 C17 H17B 106.0(54) . . . ? H17A C17 H17B 109.0(102) . . . ? C18 C19 H19 119.4(63) . . . ? C20 C19 H19 118.6(63) . . . ? C19 C20 H20 119.9(65) . . . ? C21 C20 H20 119.8(65) . . . ? C20 C21 H21 120.6(56) . . . ? C22 C21 H21 121.5(56) . . . ? C21 C22 H22 118.5(76) . . . ? C23 C22 H22 118.5(76) . . . ? 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 O1 C1 C2 C3 -168.2(13) . . . . yes O1 C1 C2 C7 11.3(9) . . . . yes O1 C1 C6 C5 165.8(13) . . . . yes O1 C1 C6 C9 -121.7(12) . . . . yes C6 C1 C2 C3 9.5(8) . . . . yes C2 C1 C6 C5 -11.9(8) . . . . yes C6 C1 C2 C7 -171.0(12) . . . . yes C2 C1 C6 C9 60.6(9) . . . . yes C1 C2 C3 C4 3.5(8) . . . . yes C7 C2 C3 C4 -175.9(15) . . . . yes C2 C3 C4 O2 164.0(14) . . . . yes C2 C3 C4 C5 -14.2(9) . . . . yes O2 C4 C5 C6 -167.3(12) . . . . yes O2 C4 C5 C8 -22.1(9) . . . . yes O2 C4 C5 C9 124.6(11) . . . . yes C3 C4 C5 C6 10.8(8) . . . . yes C3 C4 C5 C8 156.1(11) . . . . yes C3 C4 C5 C9 -57.2(9) . . . . yes C4 C5 C6 C1 1.5(8) . . . . yes C4 C5 C6 C9 -109.3(8) . . . . yes C4 C5 C9 C6 105.1(9) . . . . yes C4 C5 C9 C10 -5.0(7) . . . . yes C4 C5 C9 C23 -147.1(11) . . . . yes C8 C5 C6 C1 -142.3(11) . . . . yes C8 C5 C6 C9 106.8(9) . . . . yes C9 C5 C6 C1 110.9(9) . . . . yes C6 C5 C9 C6 0.0(6) . . . . yes C9 C5 C6 C9 0.0(5) . . . . yes C6 C5 C9 C10 -110.1(8) . . . . yes C6 C5 C9 C23 107.8(8) . . . . yes C8 C5 C9 C6 -109.0(9) . . . . yes C8 C5 C9 C10 140.9(11) . . . . yes C8 C5 C9 C23 -1.2(8) . . . . yes C1 C6 C9 C5 -110.0(9) . . . . yes C1 C6 C9 C10 -0.8(8) . . . . yes C1 C6 C9 C23 142.4(11) . . . . yes C5 C6 C9 C5 0.0(5) . . . . yes C5 C6 C9 C10 109.2(8) . . . . yes C5 C6 C9 C23 -107.6(8) . . . . yes C5 C9 C10 C11 113.7(11) . . . . yes C5 C9 C10 C15 -71.8(9) . . . . yes C5 C9 C23 C18 88.4(10) . . . . yes C5 C9 C23 C22 -93.6(10) . . . . yes C6 C9 C10 C11 43.7(9) . . . . yes C6 C9 C10 C15 -141.9(11) . . . . yes C6 C9 C23 C18 156.6(12) . . . . yes C6 C9 C23 C22 -25.5(9) . . . . yes C23 C9 C10 C11 -101.8(10) . . . . yes C23 C9 C10 C15 72.7(9) . . . . yes C10 C9 C23 C18 -56.9(9) . . . . yes C10 C9 C23 C22 121.0(11) . . . . yes C9 C10 C11 C12 178.8(13) . . . . yes C9 C10 C15 C14 -179.2(12) . . . . yes C9 C10 C15 C16 -1.6(8) . . . . yes C15 C10 C11 C12 4.4(9) . . . . yes C11 C10 C15 C14 -4.7(9) . . . . yes C11 C10 C15 C16 173.0(13) . . . . yes C10 C11 C12 C13 -1.6(9) . . . . yes C11 C12 C13 C14 -0.8(10) . . . . yes C12 C13 C14 C15 0.5(10) . . . . yes C13 C14 C15 C10 2.3(9) . . . . yes C13 C14 C15 C16 -175.3(14) . . . . yes C10 C15 C16 C17 -69.8(10) . . . . yes C14 C15 C16 C17 107.8(11) . . . . yes C15 C16 C17 C18 55.5(9) . . . . yes C16 C17 C18 C19 -179.7(13) . . . . yes C16 C17 C18 C23 -0.6(9) . . . . yes C17 C18 C19 C20 179.0(15) . . . . yes C17 C18 C23 C9 0.7(9) . . . . yes C17 C18 C23 C22 -177.3(14) . . . . yes C19 C18 C23 C9 179.7(14) . . . . yes C23 C18 C19 C20 -0.1(10) . . . . yes C19 C18 C23 C22 1.8(9) . . . . yes C18 C19 C20 C21 -1.0(11) . . . . yes C19 C20 C21 C22 0.5(11) . . . . yes C20 C21 C22 C23 1.2(11) . . . . yes C21 C22 C23 C9 179.6(15) . . . . yes C21 C22 C23 C18 -2.3(10) . . . . yes O1 C1 C6 H6 2.5(8) . . . . ? C2 C1 C6 H6 -175.2(12) . . . . ? C1 C2 C3 H3 -174.1(66) . . . . ? C1 C2 C7 H7A -179.6(63) . . . . ? C1 C2 C7 H7B 59.3(63) . . . . ? C1 C2 C7 H7C -59.0(69) . . . . ? C3 C2 C7 H7A -0.2(63) . . . . ? C3 C2 C7 H7B -121.3(63) . . . . ? C3 C2 C7 H7C 120.4(70) . . . . ? C7 C2 C3 H3 6.5(65) . . . . ? H3 C3 C4 O2 -18.4(66) . . . . ? H3 C3 C4 C5 163.4(67) . . . . ? C4 C5 C6 H6 164.6(12) . . . . ? C4 C5 C8 H8A -179.3(67) . . . . ? C4 C5 C8 H8B 58.5(86) . . . . ? C4 C5 C8 H8C -59.9(72) . . . . ? C6 C5 C8 H8A -35.1(66) . . . . ? C6 C5 C8 H8B -157.3(87) . . . . ? C6 C5 C8 H8C 84.3(72) . . . . ? C8 C5 C6 H6 20.7(8) . . . . ? C9 C5 C6 H6 -86.1(9) . . . . ? C9 C5 C8 H8A 33.6(66) . . . . ? C9 C5 C8 H8B -88.6(86) . . . . ? C9 C5 C8 H8C 153.1(72) . . . . ? H6 C6 C9 C5 118.1(8) . . . . ? H6 C6 C9 C10 -132.7(10) . . . . ? H6 C6 C9 C23 10.5(7) . . . . ? C9 C10 C11 H11 -0.7(65) . . . . ? C15 C10 C11 H11 -175.1(66) . . . . ? C10 C11 C12 H12 178.2(59) . . . . ? H11 C11 C12 C13 177.9(67) . . . . ? H11 C11 C12 H12 -2.3(87) . . . . ? C11 C12 C13 H13 178.9(16) . . . . ? H12 C12 C13 C14 179.4(59) . . . . ? H12 C12 C13 H13 -0.9(58) . . . . ? C12 C13 C14 H14 -178.7(16) . . . . ? H13 C13 C14 C15 -179.3(17) . . . . ? H13 C13 C14 H14 1.5(10) . . . . ? H14 C14 C15 C10 -178.5(14) . . . . ? H14 C14 C15 C16 3.9(9) . . . . ? C10 C15 C16 H16A 168.2(12) . . . . ? C10 C15 C16 H16B 49.1(9) . . . . ? C14 C15 C16 H16A -14.2(9) . . . . ? C14 C15 C16 H16B -133.3(12) . . . . ? C15 C16 C17 H17A -66.6(91) . . . . ? C15 C16 C17 H17B 176.7(57) . . . . ? H16A C16 C17 C18 177.9(13) . . . . ? H16A C16 C17 H17A 55.8(91) . . . . ? H16A C16 C17 H17B -60.9(56) . . . . ? H16B C16 C17 C18 -63.3(10) . . . . ? H16B C16 C17 H17A 174.7(91) . . . . ? H16B C16 C17 H17B 58.0(56) . . . . ? H17A C17 C18 C19 -58.2(92) . . . . ? H17A C17 C18 C23 120.9(92) . . . . ? H17B C17 C18 C19 58.2(56) . . . . ? H17B C17 C18 C23 -122.7(56) . . . . ? C17 C18 C19 H19 -3.1(72) . . . . ? C23 C18 C19 H19 177.7(73) . . . . ? C18 C19 C20 H20 -177.9(76) . . . . ? H19 C19 C20 C21 -178.9(73) . . . . ? H19 C19 C20 H20 4.3(103) . . . . ? C19 C20 C21 H21 179.3(64) . . . . ? H20 C20 C21 C22 177.3(76) . . . . ? H20 C20 C21 H21 -3.9(97) . . . . ? C20 C21 C22 H22 -178.2(89) . . . . ? H21 C21 C22 C23 -177.5(65) . . . . ? H21 C21 C22 H22 3.0(107) . . . . ? H22 C22 C23 C9 -0.9(87) . . . . ? H22 C22 C23 C18 177.1(88) . . . . ? #===================================================