#------------------------------------------------------------------------------ #$Date: 2012-02-03 19:16:24 +0200 (Fri, 03 Feb 2012) $ #$Revision: 32112 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/00/56/2005687.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_2005687 loop_ _publ_author_name 'Muneer, M.' 'George, M. V.' 'Rath, N. P.' _publ_section_title ; The Photoproduct Derived from 9-Cyanodibenzobarrelene ; _journal_issue 11 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 2800 _journal_page_last 2802 _journal_volume 52 _journal_year 1996 _chemical_formula_moiety 'C31 H19 N1 O2' _chemical_formula_sum 'C31 H19 N O2' _chemical_formula_weight 437.47 _chemical_name_systematic ; ; _space_group_IT_number 14 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2yn' _symmetry_space_group_name_H-M 'P 1 21/n 1' _audit_creation_method SHELXL _cell_angle_alpha 90. _cell_angle_beta 91.73(3) _cell_angle_gamma 90. _cell_formula_units_Z 4 _cell_length_a 9.078(2) _cell_length_b 14.909(3) _cell_length_c 16.576(3) _cell_measurement_reflns_used 25 _cell_measurement_temperature 298(2) _cell_measurement_theta_max 15.0 _cell_measurement_theta_min 10.0 _cell_volume 2242.4(8) _computing_cell_refinement XSCANS _computing_data_collection 'XSCANS (Siemens, 1994)' _computing_data_reduction 'SHELXTL-Plus (Sheldrick, 1995)' _computing_molecular_graphics SHELXTL-Plus _computing_publication_material SHELXTL-Plus _computing_structure_refinement SHELXTL-Plus _computing_structure_solution 'SHELXS86 (Sheldrick, 1990)' _diffrn_ambient_temperature 298(2) _diffrn_measurement_device 'Siemens P4' _diffrn_measurement_method \w-2\q _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54178 _diffrn_reflns_av_R_equivalents 0.0325 _diffrn_reflns_av_sigmaI/netI 0.0359 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -1 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_k_min -1 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_number 3943 _diffrn_reflns_theta_max 56.70 _diffrn_reflns_theta_min 3.99 _diffrn_standards_decay_% 3 _diffrn_standards_interval_count 100 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu 0.639 _exptl_absorpt_correction_type none _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.296 _exptl_crystal_density_meas no _exptl_crystal_density_method none _exptl_crystal_description rectangular _exptl_crystal_F_000 912 _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.30 _refine_diff_density_max 0.127 _refine_diff_density_min -0.188 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_all 1.304 _refine_ls_goodness_of_fit_obs 1.378 _refine_ls_hydrogen_treatment noref _refine_ls_matrix_type full _refine_ls_number_parameters 307 _refine_ls_number_reflns 2951 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.337 _refine_ls_restrained_S_obs 1.378 _refine_ls_R_factor_all 0.0539 _refine_ls_R_factor_obs 0.0423 _refine_ls_shift/esd_max 0.000 _refine_ls_shift/esd_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_scheme ; calc w = 1/[\s^2^(F~o~^2^) + (0.057P)^2^] where P = (F~o~^2^ + 2F~c~^2^)/3 ; _refine_ls_wR_factor_all 0.1184 _refine_ls_wR_factor_obs 0.1098 _reflns_number_observed 2455 _reflns_number_total 2969 _reflns_observed_criterion >2sigma(I) _[local]_cod_data_source_file sz1023.cif _[local]_cod_data_source_block mvg2594 _[local]_cod_cif_authors_sg_H-M 'P 21/n' _[local]_cod_chemical_formula_sum_orig 'C31 H19 N1 O2' _cod_database_code 2005687 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' loop_ _atom_site_label _atom_site_occupancy _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_thermal_displace_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_type_symbol O1 1 0.0850(2) 0.94300(10) 0.07783(9) 0.0637(4) Uani d . O O2 1 0.3348(2) 0.78629(10) 0.11312(10) 0.0682(5) Uani d . O N 1 -0.0374(2) 0.7790(2) 0.20924(12) 0.0756(6) Uani d . N C1 1 0.2382(2) 0.58254(13) -0.05034(12) 0.0481(5) Uani d . C H1a 1 0.2733(2) 0.55153(13) -0.00503(12) 0.058 Uiso calc R H C2 1 0.2590(2) 0.54931(15) -0.12697(13) 0.0566(6) Uani d . C H2a 1 0.3109(2) 0.49606(15) -0.13294(13) 0.068 Uiso calc R H C3 1 0.2049(3) 0.5930(2) -0.19460(13) 0.0598(6) Uani d . C H3a 1 0.2226(3) 0.5701(2) -0.24557(13) 0.072 Uiso calc R H C4 1 0.1237(2) 0.67161(15) -0.18692(12) 0.0542(6) Uani d . C H4a 1 0.0827(2) 0.69992(15) -0.23227(12) 0.065 Uiso calc R H C4a 1 0.1050(2) 0.70678(13) -0.11104(11) 0.0427(5) Uani d . C C4b 1 0.0157(2) 0.78803(13) -0.08573(11) 0.0437(5) Uani d . C H4ba 1 0.0177(2) 0.83847(13) -0.12359(11) 0.052 Uiso calc R H C4c 1 -0.1375(2) 0.75190(12) -0.07033(11) 0.0443(5) Uani d . C C5 1 -0.2544(2) 0.73652(14) -0.12426(13) 0.0548(6) Uani d . C H5a 1 -0.2491(2) 0.75376(14) -0.17800(13) 0.066 Uiso calc R H C6 1 -0.3797(2) 0.6949(2) -0.09635(14) 0.0615(6) Uani d . C H6a 1 -0.4599(2) 0.6852(2) -0.13152(14) 0.074 Uiso calc R H C7 1 -0.3866(2) 0.6677(2) -0.01713(15) 0.0614(6) Uani d . C H7a 1 -0.4708(2) 0.6387(2) 0.00013(15) 0.074 Uiso calc R H C8 1 -0.2706(2) 0.68272(14) 0.03716(13) 0.0522(5) Uani d . C H8a 1 -0.2760(2) 0.66472(14) 0.09071(13) 0.063 Uiso calc R H C8a 1 -0.1466(2) 0.72518(12) 0.00971(11) 0.0426(5) Uani d . C C8b 1 -0.0126(2) 0.75429(12) 0.05621(11) 0.0417(5) Uani d . C C8c 1 0.0803(2) 0.80965(12) 0.00045(11) 0.0416(5) Uani d . C C8d 1 0.1470(2) 0.72218(12) 0.02983(11) 0.0399(4) Uani d . C C8e 1 0.1637(2) 0.66325(12) -0.04245(11) 0.0403(5) Uani d . C C9 1 -0.0256(2) 0.77227(14) 0.14103(13) 0.0503(5) Uani d . C C10 1 0.1362(2) 0.90259(13) 0.02140(12) 0.0454(5) Uani d . C C11 1 0.2483(2) 0.94290(13) -0.03103(12) 0.0458(5) Uani d . C C12 1 0.2790(2) 1.03365(14) -0.02334(13) 0.0545(5) Uani d . C H12a 1 0.2262(2) 1.06842(14) 0.01232(13) 0.065 Uiso calc R H C13 1 0.3872(3) 1.07272(15) -0.06822(15) 0.0624(6) Uani d . C H13a 1 0.4071(3) 1.13364(15) -0.06271(15) 0.075 Uiso calc R H C14 1 0.4657(3) 1.0219(2) -0.12100(15) 0.0630(6) Uani d . C H14a 1 0.5392(3) 1.0484(2) -0.15078(15) 0.076 Uiso calc R H C15 1 0.4359(3) 0.9320(2) -0.12997(14) 0.0630(6) Uani d . C H15a 1 0.4883(3) 0.8979(2) -0.16631(14) 0.076 Uiso calc R H C16 1 0.3279(2) 0.89227(14) -0.08489(13) 0.0539(5) Uani d . C H16a 1 0.3085(2) 0.83132(14) -0.09070(13) 0.065 Uiso calc R H C17 1 0.2611(2) 0.71994(13) 0.09812(12) 0.0443(5) Uani d . C C18 1 0.2779(2) 0.63601(13) 0.14522(11) 0.0436(5) Uani d . C C19 1 0.4050(2) 0.6228(2) 0.19261(12) 0.0558(6) Uani d . C H19a 1 0.4793(2) 0.6657(2) 0.19365(12) 0.067 Uiso calc R H C20 1 0.4206(3) 0.5450(2) 0.23851(13) 0.0679(7) Uani d . C H20a 1 0.5054(3) 0.5360(2) 0.27033(13) 0.081 Uiso calc R H C21 1 0.3113(3) 0.4817(2) 0.23689(14) 0.0718(7) Uani d . C H21a 1 0.3222(3) 0.4300(2) 0.26787(14) 0.086 Uiso calc R H C22 1 0.1870(3) 0.4938(2) 0.19040(14) 0.0686(7) Uani d . C H22a 1 0.1139(3) 0.4501(2) 0.18932(14) 0.082 Uiso calc R H C23 1 0.1689(2) 0.57061(14) 0.14481(13) 0.0537(5) Uani d . C H23a 1 0.0831(2) 0.57869(14) 0.11359(13) 0.064 Uiso calc R H 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 0.0782(11) 0.0522(9) 0.0611(9) -0.0089(8) 0.0098(8) -0.0135(8) O2 0.0679(10) 0.0558(9) 0.0794(11) -0.0234(8) -0.0208(8) 0.0112(8) N 0.0809(15) 0.095(2) 0.0516(13) 0.0000(12) 0.0086(10) -0.0086(11) C1 0.0446(11) 0.0448(12) 0.0551(12) -0.0023(9) 0.0027(9) 0.0002(10) C2 0.0567(13) 0.0482(13) 0.0654(14) 0.0016(10) 0.0092(11) -0.0089(11) C3 0.0649(14) 0.0612(14) 0.0539(13) -0.0067(11) 0.0122(11) -0.0137(11) C4 0.0595(13) 0.0588(14) 0.0446(11) -0.0074(11) 0.0025(9) -0.0022(10) C4a 0.0410(11) 0.0405(10) 0.0465(11) -0.0082(8) 0.0018(8) 0.0007(9) C4b 0.0493(11) 0.0389(10) 0.0427(10) -0.0039(9) -0.0028(8) 0.0028(8) C4c 0.0446(11) 0.0370(10) 0.0512(11) 0.0011(9) -0.0017(9) -0.0024(9) C5 0.0537(13) 0.0560(13) 0.0541(12) 0.0028(10) -0.0092(10) -0.0035(10) C6 0.0418(12) 0.0679(15) 0.074(2) -0.0026(11) -0.0110(11) -0.0130(13) C7 0.0399(11) 0.0640(15) 0.080(2) -0.0089(11) 0.0030(10) -0.0070(13) C8 0.0441(12) 0.0501(12) 0.0627(13) -0.0046(9) 0.0062(10) -0.0002(10) C8a 0.0397(11) 0.0366(10) 0.0513(11) 0.0001(8) -0.0008(9) -0.0022(9) C8b 0.0408(11) 0.0398(10) 0.0446(10) -0.0010(8) 0.0027(8) 0.0013(9) C8c 0.0437(11) 0.0365(10) 0.0446(10) -0.0038(8) 0.0012(8) 0.0022(9) C8d 0.0386(10) 0.0378(10) 0.0435(10) -0.0037(8) 0.0014(8) 0.0021(8) C8e 0.0376(10) 0.0378(10) 0.0457(10) -0.0073(8) 0.0038(8) -0.0009(9) C9 0.0465(12) 0.0512(12) 0.0533(14) -0.0026(9) 0.0048(9) -0.0006(10) C10 0.0484(12) 0.0382(11) 0.0493(11) -0.0014(9) -0.0040(9) -0.0006(10) C11 0.0444(11) 0.0380(11) 0.0545(12) -0.0058(9) -0.0064(9) 0.0037(9) C12 0.0551(12) 0.0396(11) 0.0684(13) -0.0026(10) -0.0055(10) 0.0015(10) C13 0.0611(14) 0.0407(12) 0.085(2) -0.0125(11) -0.0078(12) 0.0143(12) C14 0.0589(14) 0.0611(15) 0.0687(14) -0.0149(12) -0.0017(11) 0.0187(13) C15 0.0616(14) 0.0612(15) 0.0666(14) -0.0077(12) 0.0095(11) 0.0025(12) C16 0.0560(13) 0.0420(11) 0.0638(13) -0.0091(10) 0.0036(11) -0.0011(10) C17 0.0388(11) 0.0444(11) 0.0497(11) -0.0072(9) 0.0015(8) -0.0004(9) C18 0.0428(11) 0.0481(12) 0.0401(10) 0.0012(9) 0.0028(8) -0.0015(9) C19 0.0516(13) 0.0606(14) 0.0548(12) 0.0077(10) -0.0045(10) -0.0076(11) C20 0.080(2) 0.070(2) 0.0526(13) 0.0292(14) -0.0144(11) -0.0053(12) C21 0.102(2) 0.0544(14) 0.0589(14) 0.0118(15) 0.0006(14) 0.0087(12) C22 0.082(2) 0.0538(14) 0.0702(15) -0.0060(12) 0.0069(13) 0.0142(12) C23 0.0517(12) 0.0513(13) 0.0580(12) -0.0020(10) 0.0025(10) 0.0090(11) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 C1 C8e 118.5(2) ? C3 C2 C1 121.6(2) ? C2 C3 C4 120.1(2) ? C4a C4 C3 118.9(2) ? C4 C4a C8e 120.7(2) yes C4 C4a C4b 129.4(2) yes C8e C4a C4b 109.7(2) yes C4c C4b C4a 105.1(2) yes C4c C4b C8c 103.86(15) yes C4a C4b C8c 103.18(15) yes C5 C4c C8a 120.1(2) yes C5 C4c C4b 129.6(2) yes C8a C4c C4b 110.1(2) yes C4c C5 C6 118.6(2) ? C7 C6 C5 120.7(2) ? C6 C7 C8 121.1(2) ? C8a C8 C7 118.2(2) ? C8 C8a C4c 121.2(2) yes C8 C8a C8b 128.8(2) yes C4c C8a C8b 109.9(2) yes C9 C8b C8a 118.1(2) yes C9 C8b C8c 123.9(2) yes C8a C8b C8c 107.8(2) yes C9 C8b C8d 115.1(2) yes C8a C8b C8d 120.3(2) yes C8c C8b C8d 58.02(12) yes C8d C8c C10 126.0(2) yes C8d C8c C8b 63.79(12) yes C10 C8c C8b 123.2(2) yes C8d C8c C4b 104.61(15) yes C10 C8c C4b 120.9(2) yes C8b C8c C4b 104.19(15) yes C8e C8d C8c 107.33(15) yes C8e C8d C17 120.1(2) yes C8c C8d C17 121.3(2) yes C8e C8d C8b 120.62(15) yes C8c C8d C8b 58.19(12) yes C17 C8d C8b 114.08(15) yes C1 C8e C4a 120.0(2) yes C1 C8e C8d 130.2(2) yes C4a C8e C8d 109.4(2) yes N C9 C8b 174.3(2) yes O1 C10 C11 122.3(2) yes O1 C10 C8c 119.8(2) yes C11 C10 C8c 117.9(2) ? C12 C11 C16 118.8(2) ? C12 C11 C10 118.7(2) ? C16 C11 C10 122.4(2) ? C13 C12 C11 120.5(2) ? C14 C13 C12 120.2(2) ? C13 C14 C15 120.2(2) ? C14 C15 C16 119.9(2) ? C15 C16 C11 120.4(2) ? O2 C17 C18 122.2(2) yes O2 C17 C8d 119.7(2) yes C18 C17 C8d 118.1(2) ? C23 C18 C19 118.8(2) ? C23 C18 C17 121.9(2) ? C19 C18 C17 119.2(2) ? C18 C19 C20 119.7(2) ? C21 C20 C19 120.1(2) ? C22 C21 C20 120.6(2) ? C21 C22 C23 120.3(2) ? C22 C23 C18 120.5(2) ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag O1 C10 1.217(2) yes O2 C17 1.216(2) yes N C9 1.143(3) yes C1 C2 1.382(3) ? C1 C8e 1.388(3) yes C2 C3 1.375(3) ? C3 C4 1.392(3) ? C4 C4A 1.378(3) yes C4a C8e 1.401(3) yes C4a C4b 1.523(3) yes C4b C4c 1.520(3) yes C4b C8c 1.561(3) yes C4c C5 1.386(3) yes C4c C8a 1.390(3) yes C5 C6 1.387(3) ? C6 C7 1.378(3) ? C7 C8 1.383(3) ? C8 C8a 1.381(3) yes C8a C8b 1.485(3) yes C8b C9 1.440(3) yes C8b C8c 1.515(3) yes C8b C8d 1.599(3) yes C8c C8d 1.512(3) yes C8c C10 1.512(3) yes C8d C8e 1.497(3) yes C8d C17 1.512(3) yes C10 C11 1.485(3) ? C11 C12 1.386(3) ? C11 C16 1.389(3) ? C12 C13 1.379(3) ? C13 C14 1.372(3) ? C14 C15 1.374(3) ? C15 C16 1.384(3) ? C17 C18 1.480(3) ? C18 C23 1.389(3) ? C18 C19 1.391(3) ? C19 C20 1.392(3) ? C20 C21 1.369(4) ? C21 C22 1.359(3) ? C22 C23 1.379(3) ? 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 C8e C1 C2 C3 -1.6(3) C1 C2 C3 C4 -1.6(3) C2 C3 C4 C4a 3.1(3) C3 C4 C4a C8e -1.4(3) C3 C4 C4a C4b -176.5(2) C4 C4a C4b C4c 89.3(2) C8e C4a C4b C4c -86.2(2) C4 C4a C4b C8c -162.1(2) C8e C4a C4b C8c 22.4(2) C4a C4b C4c C5 -84.4(2) C8c C4b C4c C5 167.5(2) C4a C4b C4c C8a 89.5(2) C8c C4b C4c C8a -18.5(2) C8a C4c C5 C6 0.5(3) C4b C4c C5 C6 173.9(2) C4c C5 C6 C7 -1.3(3) C5 C6 C7 C8 1.4(4) C6 C7 C8 C8a -0.5(3) C7 C8 C8a C4c -0.3(3) C7 C8 C8a C8b 175.6(2) C5 C4c C8a C8 0.3(3) C4b C4c C8a C8 -174.3(2) C5 C4c C8a C8b -176.3(2) C4b C4c C8a C8b 9.1(2) C8 C8a C8b C9 -25.0(3) C4c C8a C8b C9 151.3(2) C8 C8a C8b C8c -171.7(2) C4c C8a C8b C8c 4.6(2) C8 C8a C8b C8d 125.5(2) C4c C8a C8b C8d -58.2(2) C9 C8b C8c C8d 100.5(2) C8a C8b C8c C8d -115.2(2) C8d C8b C8c C8d 0.0 C9 C8b C8c C10 -16.9(3) C8a C8b C8c C10 127.4(2) C8d C8b C8c C10 -117.4(2) C9 C8b C8c C4b -159.9(2) C8a C8b C8c C4b -15.6(2) C8d C8b C8c C4b 99.5(2) C4c C4b C8c C8d 86.3(2) C4a C4b C8c C8d -23.2(2) C4c C4b C8c C10 -124.0(2) C4a C4b C8c C10 126.5(2) C4c C4b C8c C8b 20.2(2) C4a C4b C8c C8b -89.4(2) C10 C8c C8d C8e -130.8(2) C8b C8c C8d C8e 115.7(2) C4b C8c C8d C8e 16.9(2) C10 C8c C8d C17 12.8(3) C8b C8c C8d C17 -100.7(2) C4b C8c C8d C17 160.5(2) C10 C8c C8d C8b 113.4(2) C8b C8c C8d C8b 0.0 C4b C8c C8d C8b -98.9(2) C9 C8b C8d C8e 152.0(2) C8a C8b C8d C8e 0.6(3) C8c C8b C8d C8e -92.3(2) C9 C8b C8d C8c -115.7(2) C8a C8b C8d C8c 92.9(2) C8c C8b C8d C8c 0.0 C9 C8b C8d C17 -2.7(2) C8a C8b C8d C17 -154.0(2) C8c C8b C8d C17 113.1(2) C2 C1 C8e C4a 3.3(3) C2 C1 C8e C8d -168.6(2) C4 C4a C8e C1 -1.8(3) C4b C4a C8e C1 174.1(2) C4 C4a C8e C8d 171.6(2) C4b C4a C8e C8d -12.4(2) C8c C8d C8e C1 169.3(2) C17 C8d C8e C1 25.2(3) C8b C8d C8e C1 -127.9(2) C8c C8d C8e C4a -3.3(2) C17 C8d C8e C4a -147.4(2) C8b C8d C8e C4a 59.5(2) C8a C8b C9 N 70.(2) C8c C8b C9 N -149.(2) C8d C8b C9 N -82.(2) C8d C8c C10 O1 -93.8(2) C8b C8c C10 O1 -13.9(3) C4b C8c C10 O1 123.3(2) C8d C8c C10 C11 89.1(2) C8b C8c C10 C11 168.9(2) C4b C8c C10 C11 -53.9(2) O1 C10 C11 C12 -10.1(3) C8c C10 C11 C12 167.1(2) O1 C10 C11 C16 167.1(2) C8c C10 C11 C16 -15.8(3) C16 C11 C12 C13 -0.3(3) C10 C11 C12 C13 176.9(2) C11 C12 C13 C14 0.0(3) C12 C13 C14 C15 0.6(3) C13 C14 C15 C16 -0.9(4) C14 C15 C16 C11 0.6(3) C12 C11 C16 C15 0.0(3) C10 C11 C16 C15 -177.1(2) C8e C8d C17 O2 115.5(2) C8c C8d C17 O2 -23.5(3) C8b C8d C17 O2 -89.7(2) C8e C8d C17 C18 -65.0(2) C8c C8d C17 C18 155.9(2) C8b C8d C17 C18 89.7(2) O2 C17 C18 C23 160.7(2) C8d C17 C18 C23 -18.7(3) O2 C17 C18 C19 -17.9(3) C8d C17 C18 C19 162.6(2) C23 C18 C19 C20 -0.1(3) C17 C18 C19 C20 178.6(2) C18 C19 C20 C21 0.1(3) C19 C20 C21 C22 0.3(4) C20 C21 C22 C23 -0.6(4) C21 C22 C23 C18 0.7(3) C19 C18 C23 C22 -0.3(3) C17 C18 C23 C22 -179.0(2)