#------------------------------------------------------------------------------ #$Date: 2016-02-14 16:26:36 +0200 (Sun, 14 Feb 2016) $ #$Revision: 176435 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/01/43/2014361.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/. The original data for this entry # were provided by IUCr Journals, http://journals.iucr.org/. # # The file may be used within the scientific community so long as # proper attribution is given to the journal article from which the # data were obtained. # data_2014361 loop_ _publ_author_name ' Asahara, Haruyasu ' ' Koizumi, Takuya ' ' Mochizuki, Eiko ' ' Oshima, Takumi ' _publ_section_title ; Two conformers of 10,11-dihydro-5H-dibenzo[a,d]cycloheptene spiro-linked with homobenzoquinone epoxide ; _journal_coeditor_code HJ1087 _journal_issue 3 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first o136 _journal_page_last o138 _journal_paper_doi 10.1107/S0108270106002800 _journal_volume 62 _journal_year 2006 _chemical_formula_iupac 'C23 H20 O3 ' _chemical_formula_moiety 'C23 H20 O3 ' _chemical_formula_sum 'C23 H20 O3' _chemical_formula_weight 344.41 _chemical_melting_point 152.6(5) _space_group_IT_number 61 _symmetry_cell_setting orthorhombic _symmetry_space_group_name_Hall '-P 2ac 2ab' _symmetry_space_group_name_H-M 'P b c a' _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_formula_units_Z 8 _cell_length_a 9.4653(3) _cell_length_b 14.6974(4) _cell_length_c 25.3890(9) _cell_measurement_reflns_used 38732 _cell_measurement_temperature 213.2 _cell_measurement_theta_max 27.5 _cell_measurement_theta_min 1.6 _cell_volume 3532.00(19) _computing_cell_refinement PROCESS-AUTO _computing_data_collection 'PROCESS-AUTO (Rigaku Corporation, 1998)' _computing_data_reduction 'TEXSAN (Molecular Structure Corporation & Rigaku Corporation, 2000' _computing_publication_material TEXSAN _computing_structure_refinement TEXSAN _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _diffrn_detector_area_resol_mean 8.00 _diffrn_measured_fraction_theta_full 0.9828 _diffrn_measured_fraction_theta_max 0.9828 _diffrn_measurement_device_type 'Rigaku R-AXIS RAPID imaging-plate' _diffrn_measurement_method \w _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.7107 _diffrn_reflns_av_R_equivalents 0.085 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_l_max 32 _diffrn_reflns_limit_l_min -32 _diffrn_reflns_number 26252 _diffrn_reflns_theta_full 27.42 _diffrn_reflns_theta_max 27.42 _exptl_absorpt_coefficient_mu 0.085 _exptl_absorpt_correction_T_max 0.992 _exptl_absorpt_correction_T_min 0.974 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(Higashi, 1995)' _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.295 _exptl_crystal_density_method 'not measured' _exptl_crystal_description platelet _exptl_crystal_size_max 0.300 _exptl_crystal_size_mid 0.300 _exptl_crystal_size_min 0.100 _refine_diff_density_max 0.54 _refine_diff_density_min -0.45 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.900 _refine_ls_hydrogen_treatment constr _refine_ls_number_parameters 235 _refine_ls_number_reflns 3955 _refine_ls_R_factor_gt 0.0770 _refine_ls_shift/su_max 0.0079 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^) + (0.05000(Max(Fo^2^,0) + 2Fc^2^)/3)^2^]' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_ref 0.1761 _reflns_number_gt 2670 _reflns_number_total 3955 _reflns_threshold_expression F^2^>2.0\s(F^2^) _cod_data_source_file hj1087.cif _cod_data_source_block IIb _cod_depositor_comments ; The following automatic conversions were performed: '_chemical_melting_point' value '152.2-153.1' was changed to '152.6(5)' - the average value was taken and precision was estimated. Automatic conversion script Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana The following automatic conversions were performed: '_chemical_melting_point' value '152.2-153.1' was changed to '152.6(5)' - the average value was taken and precision was estimated. Automatic conversion script Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana ; _cod_original_cell_volume 3532.0(2) _cod_original_sg_symbol_H-M 'P bca' _cod_original_formula_sum 'C23 H20 O3 ' _cod_database_code 2014361 loop_ _symmetry_equiv_pos_as_xyz x,y,z 1/2+x,1/2-y,-z -x,1/2+y,1/2-z 1/2-x,-y,1/2+z -x,-y,-z 1/2-x,1/2+y,z x,1/2-y,1/2+z 1/2+x,y,1/2-z loop_ _atom_site_type_symbol _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_disorder_assembly _atom_site_disorder_group O O1 0.6459(2) 0.03250(10) 0.04870(8) 0.0353(6) Uani d . 1.00 . . O O2 0.3140(2) -0.03760(10) 0.21843(8) 0.0312(5) Uani d . 1.00 . . O O3 0.6056(2) -0.09130(10) 0.15553(8) 0.0319(5) Uani d . 1.00 . . C C1 0.7844(3) 0.0335(2) 0.14810(10) 0.0372(9) Uani d . 1.00 . . C C2 0.6357(3) 0.0025(2) 0.14030(10) 0.0246(7) Uani d . 1.00 . . C C3 0.5413(3) -0.0170(2) 0.18470(10) 0.0246(7) Uani d . 1.00 . . C C4 0.3845(3) -0.0178(2) 0.17990(10) 0.0224(7) Uani d . 1.00 . . C C5 0.3176(3) -0.00190(10) 0.12730(10) 0.0200(6) Uani d . 1.00 . . C C6 0.4138(3) 0.0210(2) 0.08210(10) 0.0198(6) Uani d . 1.00 . . C C7 0.5697(3) 0.0209(2) 0.08680(10) 0.0243(7) Uani d . 1.00 . . C C8 0.1849(3) -0.0564(2) 0.11680(10) 0.0302(8) Uani d . 1.00 . . C C9 0.3270(2) 0.0978(2) 0.10680(10) 0.0176(6) Uani d . 1.00 . . C C10 0.4003(3) 0.16860(10) 0.14060(10) 0.0178(6) Uani d . 1.00 . . C C11 0.5259(3) 0.2098(2) 0.12540(10) 0.0226(7) Uani d . 1.00 . . C C12 0.5885(3) 0.2760(2) 0.15630(10) 0.0277(7) Uani d . 1.00 . . C C13 0.5242(3) 0.3032(2) 0.20250(10) 0.0311(8) Uani d . 1.00 . . C C14 0.3967(3) 0.2648(2) 0.21720(10) 0.0268(7) Uani d . 1.00 . . C C15 0.3327(3) 0.1977(2) 0.18670(10) 0.0216(6) Uani d . 1.00 . . C C16 0.1862(3) 0.1642(2) 0.19850(10) 0.0253(7) Uani d . 1.00 . . C C17 0.0798(3) 0.2058(2) 0.16080(10) 0.0262(7) Uani d . 1.00 . . C C18 0.0918(3) 0.1841(2) 0.10230(10) 0.0237(7) Uani d . 1.00 . . C C19 -0.0192(3) 0.2169(2) 0.07090(10) 0.0365(9) Uani d . 1.00 . . C C20 -0.0256(3) 0.2029(2) 0.01750(10) 0.0426(9) Uani d . 1.00 . . C C21 0.0826(4) 0.1559(2) -0.00720(10) 0.0377(9) Uani d . 1.00 . . C C22 0.1952(3) 0.1237(2) 0.02230(10) 0.0264(7) Uani d . 1.00 . . C C23 0.2013(3) 0.1354(2) 0.07700(10) 0.0204(6) Uani d . 1.00 . . H H1 0.7937 0.0955 0.1372 0.0469 Uiso calc . 1.00 . . H H2 0.8098 0.0290 0.1843 0.0469 Uiso calc . 1.00 . . H H3 0.8477 -0.0028 0.1278 0.0469 Uiso calc . 1.00 . . H H4 0.5789 -0.0051 0.2194 0.0297 Uiso calc . 1.00 . . H H5 0.3796 0.0011 0.0484 0.0231 Uiso calc . 1.00 . . H H6 0.1151 -0.0415 0.1426 0.0374 Uiso calc . 1.00 . . H H7 0.1493 -0.0428 0.0829 0.0374 Uiso calc . 1.00 . . H H8 0.2050 -0.1198 0.1191 0.0374 Uiso calc . 1.00 . . H H9 0.5695 0.1914 0.0925 0.0275 Uiso calc . 1.00 . . H H10 0.6768 0.3032 0.1456 0.0337 Uiso calc . 1.00 . . H H11 0.5672 0.3484 0.2244 0.0380 Uiso calc . 1.00 . . H H12 0.3506 0.2849 0.2495 0.0344 Uiso calc . 1.00 . . H H13 0.1619 0.1807 0.2340 0.0305 Uiso calc . 1.00 . . H H14 0.1831 0.0996 0.1956 0.0305 Uiso calc . 1.00 . . H H15 0.0863 0.2703 0.1643 0.0304 Uiso calc . 1.00 . . H H16 -0.0123 0.1870 0.1719 0.0304 Uiso calc . 1.00 . . H H17 -0.0948 0.2493 0.0881 0.0438 Uiso calc . 1.00 . . H H18 -0.1042 0.2259 -0.0029 0.0500 Uiso calc . 1.00 . . H H19 0.0787 0.1452 -0.0441 0.0435 Uiso calc . 1.00 . . H H20 0.2708 0.0922 0.0045 0.0321 Uiso calc . 1.00 . . 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 0.0270(10) 0.0450(10) 0.0330(10) -0.0003(9) 0.0090(10) -0.0073(10) O2 0.0330(10) 0.0295(10) 0.0310(10) 0.0044(8) 0.0040(10) 0.0102(9) O3 0.0249(10) 0.0199(8) 0.0510(10) 0.0030(7) -0.0010(10) 0.0028(9) C1 0.0240(10) 0.038(2) 0.050(2) -0.0030(10) -0.009(2) 0.0060(10) C2 0.0200(10) 0.0160(10) 0.038(2) 0.0022(10) -0.0050(10) -0.0010(10) C3 0.0260(10) 0.0220(10) 0.025(2) 0.0010(10) -0.0040(10) 0.0040(10) C4 0.0270(10) 0.0150(10) 0.025(2) 0.0009(10) 0.0000(10) 0.0020(10) C5 0.0190(10) 0.0160(10) 0.026(2) -0.0012(9) -0.0010(10) 0.0000(10) C6 0.0210(10) 0.0200(10) 0.0180(10) 0.0009(10) -0.0020(10) -0.0020(10) C7 0.0240(10) 0.0220(10) 0.027(2) 0.0040(10) 0.0030(10) -0.0040(10) C8 0.0260(10) 0.0220(10) 0.043(2) -0.0050(10) -0.0060(10) 0.0020(10) C9 0.0160(10) 0.0190(10) 0.0170(10) -0.0006(9) 0.0020(10) -0.0010(10) C10 0.0180(10) 0.0160(10) 0.0200(10) 0.0022(9) -0.0030(10) 0.0019(10) C11 0.0220(10) 0.0200(10) 0.026(2) 0.0032(10) 0.0000(10) 0.0030(10) C12 0.0240(10) 0.0190(10) 0.041(2) -0.0030(10) -0.0080(10) 0.0020(10) C13 0.037(2) 0.0190(10) 0.037(2) 0.0030(10) -0.020(2) -0.0060(10) C14 0.035(2) 0.0220(10) 0.0230(10) 0.0100(10) -0.0060(10) -0.0030(10) C15 0.0230(10) 0.0200(10) 0.0210(10) 0.0075(10) -0.0030(10) 0.0000(10) C16 0.0280(10) 0.0220(10) 0.025(2) 0.0060(10) 0.0060(10) -0.0040(10) C17 0.0190(10) 0.0260(10) 0.034(2) 0.0020(10) 0.0030(10) -0.0050(10) C18 0.0200(10) 0.0200(10) 0.032(2) 0.0015(10) -0.0010(10) 0.0020(10) C19 0.0270(10) 0.0340(10) 0.048(2) 0.0100(10) 0.000(2) 0.0030(10) C20 0.036(2) 0.045(2) 0.047(2) 0.0120(10) -0.013(2) 0.010(2) C21 0.045(2) 0.040(2) 0.028(2) 0.0060(10) -0.011(2) 0.0050(10) C22 0.0250(10) 0.0270(10) 0.027(2) 0.0040(10) -0.0020(10) 0.0010(10) C23 0.0210(10) 0.0160(10) 0.025(2) -0.0012(9) -0.0030(10) 0.0010(10) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.003 0.002 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; H H 0.000 0.000 ;International Tables for Crystallography (1992, Vol. C, Table 6.1.1.2) ; O O 0.011 0.006 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_publ_flag C2 O3 C3 60.4(2) no C2 C1 H1 109.8 no C2 C1 H2 110.2 no C2 C1 H3 110.5 no H1 C1 H2 108.7 no H1 C1 H3 108.5 no H2 C1 H3 109.0 no O3 C2 C1 115.9(2) no O3 C2 C3 59.5(2) no O3 C2 C7 108.9(2) no C1 C2 C3 122.2(3) no C1 C2 C7 116.9(2) no C3 C2 C7 118.1(2) no O3 C3 C2 60.1(2) no O3 C3 C4 111.7(2) no O3 C3 H4 116.5 no C2 C3 C4 123.1(2) no C2 C3 H4 116.1 no C4 C3 H4 116.3 no O2 C4 C3 118.8(2) no O2 C4 C5 121.5(2) no C3 C4 C5 119.6(2) no C4 C5 C6 117.4(2) no C4 C5 C8 115.2(2) no C4 C5 C9 114.9(2) no C6 C5 C8 119.1(2) no C6 C5 C9 60.0(2) no C8 C5 C9 119.1(2) no C5 C6 C7 122.9(2) no C5 C6 C9 61.8(2) no C5 C6 H5 114.1 no C7 C6 C9 120.2(2) no C7 C6 H5 114.0 no C9 C6 H5 114.1 no O1 C7 C2 119.4(2) no O1 C7 C6 121.8(3) no C2 C7 C6 118.8(2) no C5 C8 H6 109.4 no C5 C8 H7 110.1 no C5 C8 H8 109.9 no H6 C8 H7 109.3 no H6 C8 H8 108.6 no H7 C8 H8 109.5 no C5 C9 C6 58.2(2) no C5 C9 C10 118.8(2) no C5 C9 C23 117.7(2) no C6 C9 C10 119.5(2) no C6 C9 C23 119.1(2) no C10 C9 C23 113.0(2) yes C9 C10 C11 122.1(2) no C9 C10 C15 118.3(2) no C11 C10 C15 119.4(2) no C10 C11 C12 120.9(2) no C10 C11 H9 118.9 no C12 C11 H9 120.1 no C11 C12 C13 119.8(2) no C11 C12 H10 120.1 no C13 C12 H10 120.1 no C12 C13 C14 119.8(3) no C12 C13 H11 120.6 no C14 C13 H11 119.7 no C13 C14 C15 121.2(3) no C13 C14 H12 119.6 no C15 C14 H12 119.2 no C10 C15 C14 118.8(2) no C10 C15 C16 119.2(2) no C14 C15 C16 121.6(2) no C15 C16 C17 110.8(2) no C15 C16 H13 108.9 no C15 C16 H14 109.9 no C17 C16 H13 109.3 no C17 C16 H14 109.5 no H13 C16 H14 108.4 no C16 C17 C18 118.7(2) no C16 C17 H15 107.4 no C16 C17 H16 107.6 no C18 C17 H15 107.2 no C18 C17 H16 107.1 no H15 C17 H16 108.5 no C17 C18 C19 115.2(2) no C17 C18 C23 127.1(2) no C19 C18 C23 117.7(3) no C18 C19 C20 122.8(3) no C18 C19 H17 118.0 no C20 C19 H17 119.2 no C19 C20 C21 119.2(3) no C19 C20 H18 120.7 no C21 C20 H18 120.1 no C20 C21 C22 119.7(3) no C20 C21 H19 120.0 no C22 C21 H19 120.3 no C21 C22 C23 121.7(3) no C21 C22 H20 118.8 no C23 C22 H20 119.6 no C9 C23 C18 122.3(2) no C9 C23 C22 118.8(2) no C18 C23 C22 118.8(2) no loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag O1 C7 . . 1.218(4) yes O2 C4 . . 1.220(3) yes O3 C2 . . 1.460(3) yes O3 C3 . . 1.452(3) yes C1 C2 . . 1.492(4) no C1 H1 . . 0.957 no C1 H2 . . 0.952 no C1 H3 . . 0.954 no C2 C3 . . 1.466(4) yes C2 C7 . . 1.521(4) no C3 C4 . . 1.490(4) no C3 H4 . . 0.967 no C4 C5 . . 1.495(4) no C5 C6 . . 1.503(4) yes C5 C8 . . 1.514(4) no C5 C9 . . 1.557(3) yes C6 C7 . . 1.480(4) no C6 C9 . . 1.530(3) yes C6 H5 . . 0.961 no C8 H6 . . 0.956 no C8 H7 . . 0.946 no C8 H8 . . 0.954 no C9 C10 . . 1.517(3) yes C9 C23 . . 1.515(4) yes C10 C11 . . 1.390(4) no C10 C15 . . 1.400(4) yes C11 C12 . . 1.384(4) no C11 H9 . . 0.970 no C12 C13 . . 1.379(4) no C12 H10 . . 0.966 no C13 C14 . . 1.384(4) no C13 H11 . . 0.958 no C14 C15 . . 1.393(4) no C14 H12 . . 0.975 no C15 C16 . . 1.502(4) yes C16 C17 . . 1.518(4) yes C16 H13 . . 0.961 no C16 H14 . . 0.952 no C17 C18 . . 1.524(4) yes C17 H15 . . 0.954 no C17 H16 . . 0.957 no C18 C19 . . 1.404(4) no C18 C23 . . 1.413(4) yes C19 C20 . . 1.374(5) no C19 H17 . . 0.963 no C20 C21 . . 1.385(5) no C20 H18 . . 0.966 no C21 C22 . . 1.385(4) no C21 H19 . . 0.950 no C22 C23 . . 1.401(4) no C22 H20 . . 0.965 no loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_2 O3 C17 3.462(3) 6_545 O3 C12 3.491(3) 6_645 O1 C22 3.284(3) 5_655 O1 C6 3.460(3) 5_655 O2 C13 3.444(3) 3_645 O2 C14 3.523(3) 6_545 O2 C1 3.557(4) 8_455 O2 C3 3.578(3) 8_455 C8 C13 3.593(4) 6_545 C13 C16 3.585(4) 8_555 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_publ_flag O3 C2 C3 C4 -97.7(3) no O3 C2 C7 O1 -111.3(3) no O3 C2 C7 C6 66.7(3) no O3 C3 C2 C1 -103.2(3) no O3 C3 C2 C7 96.4(2) no O3 C3 C4 O2 110.2(3) no O3 C3 C4 C5 -65.0(3) no O1 C7 C2 C1 22.4(3) no O1 C7 C2 C3 -176.1(2) yes O1 C7 C6 C5 174.1(2) no O1 C7 C6 C9 -111.9(3) no O2 C4 C3 C2 177.8(2) yes O2 C4 C5 C6 -179.3(2) no O2 C4 C5 C8 -31.1(3) no O2 C4 C5 C9 113.1(3) no C1 C2 O3 C3 113.7(3) no C1 C2 C3 C4 159.1(2) no C1 C2 C7 C6 -159.6(2) no C2 O3 C3 C4 116.7(3) no C2 C3 C4 C5 2.6(3) no C2 C7 C6 C5 -3.9(3) no C2 C7 C6 C9 70.1(3) no C3 O3 C2 C7 -112.1(2) no C3 C2 C7 C6 1.9(3) no C3 C4 C5 C6 -4.3(3) no C3 C4 C5 C8 143.9(2) no C3 C4 C5 C9 -71.9(3) no C4 C3 C2 C7 -1.3(3) no C4 C5 C6 C7 5.1(3) no C4 C5 C6 C9 -104.4(2) no C4 C5 C9 C6 108.5(2) no C4 C5 C9 C10 -0.2(3) no C4 C5 C9 C23 -142.8(2) no C5 C6 C9 C10 107.6(2) no C5 C6 C9 C23 -106.4(2) no C5 C9 C6 C7 -113.6(3) no C5 C9 C10 C11 113.4(3) no C5 C9 C10 C15 -71.4(3) no C5 C9 C23 C18 92.6(3) no C5 C9 C23 C22 -89.1(3) no C6 C5 C9 C10 -108.7(2) no C6 C5 C9 C23 108.7(2) no C6 C9 C5 C8 -108.8(3) no C6 C9 C10 C11 45.7(3) no C6 C9 C10 C15 -139.1(2) no C6 C9 C23 C18 159.8(2) no C6 C9 C23 C22 -21.9(3) no C7 C6 C5 C8 -141.8(2) no C7 C6 C5 C9 109.5(2) no C7 C6 C9 C10 -6.0(3) no C7 C6 C9 C23 140.1(2) no C8 C5 C6 C9 108.7(2) no C8 C5 C9 C10 142.5(2) no C8 C5 C9 C23 -0.1(4) no C9 C10 C11 C12 178.2(2) no C9 C10 C15 C14 -178.0(2) no C9 C10 C15 C16 -5.2(3) no C9 C23 C18 C17 -0.5(4) no C9 C23 C18 C19 179.3(2) no C9 C23 C22 C21 179.5(2) no C10 C9 C23 C18 -52.1(3) no C10 C9 C23 C22 126.2(2) no C10 C11 C12 C13 -1.3(4) no C10 C15 C14 C13 0.6(4) no C10 C15 C16 C17 -70.4(3) no C11 C10 C9 C23 -102.3(3) no C11 C10 C15 C14 -2.7(4) no C11 C10 C15 C16 170.1(2) no C11 C12 C13 C14 -0.8(4) no C12 C11 C10 C15 3.1(4) no C12 C13 C14 C15 1.1(4) no C13 C14 C15 C16 -172.0(2) no C14 C15 C16 C17 102.2(3) no C15 C10 C9 C23 72.9(3) no C15 C16 C17 C18 63.6(3) yes C16 C17 C18 C19 173.3(2) no C16 C17 C18 C23 -6.9(4) no C17 C18 C19 C20 -179.6(3) no C17 C18 C23 C22 -178.8(2) no C18 C19 C20 C21 -1.2(5) no C18 C23 C22 C21 -2.2(4) no C19 C18 C23 C22 1.0(3) no C19 C20 C21 C22 0.1(4) no C20 C19 C18 C23 0.6(4) no C20 C21 C22 C23 1.6(4) no C20 C21 C22 C23 1.6(4) no