#------------------------------------------------------------------------------ #$Date: 2012-12-19 13:35:58 +0200 (Wed, 19 Dec 2012) $ #$Revision: 69511 $ #$URL: file:///home/coder/svn-repositories/cod/cif/5/00/03/5000396.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/ # # All data on this site have been placed in the public domain by the # contributors. # data_5000396 loop_ _publ_author_name 'Jiajia Zhang' 'Douglas M. Ho' 'Robert A. Pascal' _publ_section_title ; Synthesis of an Extremely Crowded Naphthalene via a Stable Norbornadienone ; _journal_name_full 'Journal of the American Chemical Society' _journal_volume 123 _journal_page_first 10919 _journal_page_last 10926 _journal_year 2001 _audit_creation_method SHELXL _chemical_name_systematic ; 1,2,4-Tri(t-butyl)-5,6,7,8-tetraphenyl-9-oxo-1,4-dihydro-1,4-methanonaphthalene ; _chemical_formula_iupac 'C47 H48 O' _chemical_formula_moiety 'C47 H48 O' _chemical_formula_structural 'C47 H48 O' _chemical_formula_sum 'C47 H48 O' _[local]_cod_chemical_formula_sum_orig 'C47 H48 O1' _chemical_formula_weight 628.85 _chemical_compound_source 'chemical synthesis' 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 'monoclinic' _space_group_IT_number 15 _symmetry_space_group_name_Hall '-C 2yc' _symmetry_space_group_name_H-M 'C 1 2/c 1' _[local]_cod_cif_authors_sg_H-M 'C 2/c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 22.8785(5) _cell_length_b 12.4546(3) _cell_length_c 25.6155(5) _cell_angle_alpha 90.00 _cell_angle_beta 93.510(1) _cell_angle_gamma 90.00 _cell_volume 7285.3(3) _cell_formula_units_Z 8 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used 23848 _cell_measurement_theta_min 1.59 _cell_measurement_theta_max 24.98 _exptl_crystal_description 'Needle' _exptl_crystal_colour 'Colorless' _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.12 _exptl_crystal_density_diffrn 1.147 _exptl_crystal_F_000 2704 _exptl_absorpt_coefficient_mu 0.066 _exptl_absorpt_correction_type 'none' _exptl_special_details ; Sample mounted on a glass fiber with silicone grease ; _diffrn_ambient_temperature 200(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'Nonius KappaCCD' _diffrn_measurement_method 'omega scans; 800 0.5-degree frames' _diffrn_standards_number 0 _diffrn_reflns_number 23848 _diffrn_reflns_av_R_equivalents 0.0480 _diffrn_reflns_av_sigmaI/netI 0.0470 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 27 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -30 _diffrn_reflns_limit_l_max 30 _diffrn_reflns_theta_min 1.59 _diffrn_reflns_theta_max 24.98 _reflns_number_total 6408 _reflns_number_observed 4347 _reflns_observed_criterion >2sigma(I) _computing_data_collection 'Nonius COLLECT' _computing_cell_refinement 'DENZO-SMN' _computing_data_reduction 'DENZO-SMN' _computing_structure_solution 'Siemens SHELXTL' _computing_structure_refinement 'Siemens SHELXTL' _computing_molecular_graphics 'Siemens SHELXTL' _computing_publication_material 'Siemens SHELXTL' _refine_special_details ; Refinement on F^2^ for ALL reflections except for 1 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 'w=1/[\s^2^(Fo^2^)+(0.0549P)^2^+4.0221P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment 'XYZ riding, U(H) = 1.2U(C) or 1.5U(Cmethyl)' _refine_ls_extinction_method 'none' _refine_ls_extinction_coef 'none' _refine_ls_number_reflns 6407 _refine_ls_number_parameters 442 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0856 _refine_ls_R_factor_obs 0.0502 _refine_ls_wR_factor_all 0.1285 _refine_ls_wR_factor_obs 0.1122 _refine_ls_goodness_of_fit_all 1.028 _refine_ls_goodness_of_fit_obs 1.108 _refine_ls_restrained_S_all 1.029 _refine_ls_restrained_S_obs 1.108 _refine_ls_shift/esd_max 0.000 _refine_ls_shift/esd_mean 0.000 _refine_diff_density_max 0.156 _refine_diff_density_min -0.203 _refine_diff_density_rms 0.035 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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group O1 O 0.04512(5) 0.70626(12) 0.01946(5) 0.0435(4) Uani 1 d . . C1 C 0.11248(7) 0.6744(2) 0.09891(7) 0.0324(4) Uani 1 d . . C2 C 0.08789(8) 0.7290(2) 0.14890(6) 0.0328(4) Uani 1 d . . C3 C 0.03085(8) 0.7050(2) 0.14799(7) 0.0330(4) Uani 1 d . . H3 H 0.00559(8) 0.7298(2) 0.17349(7) 0.040 Uiso 1 calc R . C4 C 0.01054(7) 0.6345(2) 0.10243(6) 0.0313(4) Uani 1 d . . C4A C 0.04515(7) 0.5275(2) 0.11120(6) 0.0297(4) Uani 1 d . . C5 C 0.02603(7) 0.4240(2) 0.12148(6) 0.0307(4) Uani 1 d . . C6 C 0.06657(8) 0.3389(2) 0.12108(7) 0.0331(4) Uani 1 d . . C7 C 0.12601(7) 0.3597(2) 0.11614(7) 0.0338(5) Uani 1 d . . C8 C 0.14677(7) 0.4655(2) 0.11191(6) 0.0323(4) Uani 1 d . . C8A C 0.10613(7) 0.5503(2) 0.10773(6) 0.0299(4) Uani 1 d . . C9 C 0.05377(8) 0.6794(2) 0.06415(7) 0.0328(4) Uani 1 d . . C10 C 0.16268(8) 0.7269(2) 0.06853(7) 0.0367(5) Uani 1 d . . C11 C 0.22349(8) 0.7344(2) 0.09781(7) 0.0426(5) Uani 1 d . . H11A H 0.2502(2) 0.7740(9) 0.0764(2) 0.064 Uiso 1 calc R . H11B H 0.2388(2) 0.6619(2) 0.1046(4) 0.064 Uiso 1 calc R . H11C H 0.22004(12) 0.7720(9) 0.1311(2) 0.064 Uiso 1 calc R . C12 C 0.14477(9) 0.8433(2) 0.05340(8) 0.0500(6) Uani 1 d . . H12A H 0.1779(2) 0.8799(4) 0.0386(5) 0.075 Uiso 1 calc R . H12B H 0.1336(5) 0.8819(4) 0.08461(12) 0.075 Uiso 1 calc R . H12C H 0.1115(4) 0.8417(2) 0.0274(4) 0.075 Uiso 1 calc R . C13 C 0.17035(9) 0.6641(2) 0.01746(7) 0.0467(6) Uani 1 d . . H13A H 0.2082(3) 0.6824(8) 0.0038(3) 0.070 Uiso 1 calc R . H13B H 0.1387(3) 0.6831(8) -0.0084(2) 0.070 Uiso 1 calc R . H13C H 0.1690(6) 0.5868(2) 0.02459(12) 0.070 Uiso 1 calc R . C14 C 0.12030(8) 0.7831(2) 0.19629(7) 0.0400(5) Uani 1 d . . C15 C 0.14777(10) 0.8921(2) 0.18483(8) 0.0568(6) Uani 1 d . . H15A H 0.1785(4) 0.8825(2) 0.1602(4) 0.085 Uiso 1 calc R . H15B H 0.1648(6) 0.9232(6) 0.21745(12) 0.085 Uiso 1 calc R . H15C H 0.11757(15) 0.9404(4) 0.1695(5) 0.085 Uiso 1 calc R . C16 C 0.16632(9) 0.7064(2) 0.22059(8) 0.0572(6) Uani 1 d . . H16A H 0.1959(4) 0.6919(9) 0.1954(2) 0.086 Uiso 1 calc R . H16B H 0.14749(14) 0.6389(5) 0.2299(5) 0.086 Uiso 1 calc R . H16C H 0.1851(4) 0.7390(5) 0.2521(3) 0.086 Uiso 1 calc R . C17 C 0.07665(9) 0.8049(2) 0.23851(7) 0.0517(6) Uani 1 d . . H17A H 0.0588(5) 0.7371(2) 0.2487(4) 0.077 Uiso 1 calc R . H17B H 0.0460(4) 0.8539(9) 0.2246(2) 0.077 Uiso 1 calc R . H17C H 0.0973(2) 0.8375(11) 0.2692(2) 0.077 Uiso 1 calc R . C18 C -0.05507(7) 0.6459(2) 0.08210(7) 0.0362(5) Uani 1 d . . C19 C -0.09991(8) 0.6199(2) 0.12262(8) 0.0473(5) Uani 1 d . . H19A H -0.1374(2) 0.6539(9) 0.1122(3) 0.071 Uiso 1 calc R . H19B H -0.0857(3) 0.6472(10) 0.15696(14) 0.071 Uiso 1 calc R . H19C H -0.1052(4) 0.5419(2) 0.1246(4) 0.071 Uiso 1 calc R . C20 C -0.06787(8) 0.5765(2) 0.03331(7) 0.0429(5) Uani 1 d . . H20A H -0.10947(14) 0.5822(8) 0.0220(3) 0.064 Uiso 1 calc R . H20B H -0.0583(5) 0.5015(2) 0.04154(15) 0.064 Uiso 1 calc R . H20C H -0.0441(4) 0.6015(7) 0.0052(2) 0.064 Uiso 1 calc R . C21 C -0.06590(9) 0.7650(2) 0.06829(8) 0.0475(5) Uani 1 d . . H21A H -0.1049(2) 0.7731(2) 0.0508(4) 0.071 Uiso 1 calc R . H21B H -0.0363(3) 0.7896(3) 0.0450(4) 0.071 Uiso 1 calc R . H21C H -0.0634(6) 0.8080(2) 0.10038(9) 0.071 Uiso 1 calc R . C22 C -0.03303(7) 0.3981(2) 0.14019(7) 0.0334(4) Uani 1 d . . C23 C -0.07363(8) 0.3338(2) 0.11225(7) 0.0402(5) Uani 1 d . . H23 H -0.06618(8) 0.3102(2) 0.07802(7) 0.048 Uiso 1 calc R . C24 C -0.12491(9) 0.3044(2) 0.13442(9) 0.0561(6) Uani 1 d . . H24 H -0.15274(9) 0.2611(2) 0.11511(9) 0.067 Uiso 1 calc R . C25 C -0.13601(10) 0.3372(2) 0.18409(10) 0.0660(7) Uani 1 d . . H25 H -0.17137(10) 0.3165(2) 0.19892(10) 0.079 Uiso 1 calc R . C26 C -0.09595(9) 0.3999(2) 0.21234(8) 0.0612(7) Uani 1 d . . H26 H -0.10337(9) 0.4221(2) 0.24678(8) 0.073 Uiso 1 calc R . C27 C -0.04470(8) 0.4303(2) 0.19025(7) 0.0459(5) Uani 1 d . . H27 H -0.01716(8) 0.4739(2) 0.20972(7) 0.055 Uiso 1 calc R . C28 C 0.04622(8) 0.2260(2) 0.12657(7) 0.0373(5) Uani 1 d . . C29 C 0.03989(10) 0.1607(2) 0.08288(9) 0.0556(6) Uani 1 d . . H29 H 0.05000(10) 0.1878(2) 0.04996(9) 0.067 Uiso 1 calc R . C30 C 0.01916(11) 0.0569(2) 0.08617(12) 0.0718(8) Uani 1 d . . H30 H 0.01524(11) 0.0134(2) 0.05571(12) 0.086 Uiso 1 calc R . C31 C 0.00432(12) 0.0170(2) 0.13307(14) 0.0782(8) Uani 1 d . . H31 H -0.00969(12) -0.0545(2) 0.13559(14) 0.094 Uiso 1 calc R . C32 C 0.00979(13) 0.0804(2) 0.17608(12) 0.0800(8) Uani 1 d . . H32 H -0.00118(13) 0.0531(2) 0.20870(12) 0.096 Uiso 1 calc R . C33 C 0.03091(10) 0.1835(2) 0.17344(9) 0.0572(6) Uani 1 d . . H33 H 0.03497(10) 0.2259(2) 0.20428(9) 0.069 Uiso 1 calc R . C34 C 0.16779(8) 0.2668(2) 0.11863(7) 0.0381(5) Uani 1 d . . C35 C 0.18623(10) 0.2197(2) 0.07360(9) 0.0600(6) Uani 1 d . . H35 H 0.17337(10) 0.2480(2) 0.04044(9) 0.072 Uiso 1 calc R . C36 C 0.22345(11) 0.1310(2) 0.07631(12) 0.0742(8) Uani 1 d . . H36 H 0.23573(11) 0.0994(2) 0.04506(12) 0.089 Uiso 1 calc R . C37 C 0.24221(10) 0.0898(2) 0.12338(14) 0.0698(8) Uani 1 d . . H37 H 0.26734(10) 0.0290(2) 0.12511(14) 0.084 Uiso 1 calc R . C38 C 0.22493(10) 0.1356(2) 0.16809(11) 0.0649(7) Uani 1 d . . H38 H 0.23853(10) 0.1073(2) 0.20106(11) 0.078 Uiso 1 calc R . C39 C 0.18785(9) 0.2230(2) 0.16597(9) 0.0512(6) Uani 1 d . . H39 H 0.17587(9) 0.2535(2) 0.19757(9) 0.061 Uiso 1 calc R . C40 C 0.21242(8) 0.4778(2) 0.11589(8) 0.0394(5) Uani 1 d . . C41 C 0.24611(9) 0.4627(2) 0.07295(9) 0.0550(6) Uani 1 d . . H41 H 0.22742(9) 0.4452(2) 0.03991(9) 0.066 Uiso 1 calc R . C42 C 0.30617(10) 0.4728(2) 0.07780(12) 0.0725(8) Uani 1 d . . H42 H 0.32857(10) 0.4632(2) 0.04813(12) 0.087 Uiso 1 calc R . C43 C 0.33359(11) 0.4969(2) 0.12535(15) 0.0801(9) Uani 1 d . . H43 H 0.37484(11) 0.5066(2) 0.12834(15) 0.096 Uiso 1 calc R . C44 C 0.30161(10) 0.5069(2) 0.16874(11) 0.0674(7) Uani 1 d . . H44 H 0.32083(10) 0.5214(2) 0.20191(11) 0.081 Uiso 1 calc R . C45 C 0.24098(9) 0.4958(2) 0.16401(9) 0.0496(6) Uani 1 d . . H45 H 0.21908(9) 0.5006(2) 0.19426(9) 0.060 Uiso 1 calc R . 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 O1 0.0375(8) 0.0585(10) 0.0336(8) 0.0044(6) -0.0038(6) -0.0011(7) C1 0.0255(9) 0.0404(12) 0.0310(10) 0.0017(8) 0.0004(7) -0.0044(9) C2 0.0320(10) 0.0363(12) 0.0299(10) 0.0004(8) 0.0011(8) -0.0032(9) C3 0.0305(10) 0.0371(12) 0.0317(10) -0.0018(8) 0.0038(8) -0.0010(9) C4 0.0242(9) 0.0376(12) 0.0319(10) -0.0024(8) 0.0006(7) -0.0001(8) C4A 0.0228(9) 0.0400(12) 0.0262(9) -0.0035(8) -0.0008(7) -0.0011(8) C5 0.0246(9) 0.0397(12) 0.0275(9) -0.0021(8) -0.0005(7) -0.0042(9) C6 0.0293(10) 0.0386(12) 0.0311(10) -0.0018(8) -0.0008(7) -0.0023(9) C7 0.0284(10) 0.0416(12) 0.0314(10) -0.0023(8) 0.0010(7) 0.0014(9) C8 0.0235(10) 0.0425(13) 0.0309(10) -0.0009(8) 0.0018(7) -0.0001(9) C8A 0.0249(10) 0.0392(12) 0.0254(9) -0.0017(8) 0.0002(7) -0.0036(9) C9 0.0314(10) 0.0355(12) 0.0313(11) -0.0027(8) -0.0002(8) 0.0003(9) C10 0.0294(10) 0.0469(13) 0.0339(10) 0.0057(9) 0.0026(8) -0.0055(9) C11 0.0300(10) 0.0549(14) 0.0430(11) 0.0044(10) 0.0026(8) -0.0112(10) C12 0.0433(12) 0.056(2) 0.0508(13) 0.0137(11) 0.0021(10) -0.0097(11) C13 0.0358(11) 0.068(2) 0.0367(11) 0.0020(10) 0.0065(8) -0.0052(11) C14 0.0363(11) 0.0497(14) 0.0338(10) -0.0043(9) -0.0010(8) -0.0085(10) C15 0.0521(14) 0.060(2) 0.0584(14) -0.0158(12) 0.0038(11) -0.0226(12) C16 0.0496(13) 0.075(2) 0.0448(12) -0.0013(11) -0.0106(10) -0.0014(12) C17 0.0521(13) 0.067(2) 0.0362(11) -0.0136(10) 0.0022(9) -0.0113(12) C18 0.0232(10) 0.0408(13) 0.0438(11) -0.0032(9) -0.0027(8) -0.0006(9) C19 0.0265(10) 0.0556(15) 0.0599(13) -0.0072(11) 0.0038(9) 0.0014(10) C20 0.0340(11) 0.0464(14) 0.0468(12) -0.0051(10) -0.0085(9) -0.0005(10) C21 0.0338(11) 0.0500(14) 0.0576(13) -0.0045(11) -0.0064(9) 0.0061(10) C22 0.0248(10) 0.0415(12) 0.0335(10) 0.0043(8) -0.0007(8) 0.0002(9) C23 0.0282(10) 0.0474(13) 0.0440(11) 0.0062(9) -0.0047(8) -0.0056(9) C24 0.0334(12) 0.066(2) 0.068(2) 0.0175(12) -0.0077(11) -0.0158(11) C25 0.0319(12) 0.101(2) 0.066(2) 0.0272(15) 0.0098(11) -0.0096(13) C26 0.0427(13) 0.099(2) 0.0426(12) 0.0133(13) 0.0114(10) 0.0040(13) C27 0.0314(11) 0.070(2) 0.0365(11) 0.0021(10) 0.0006(8) -0.0028(11) C28 0.0264(10) 0.0395(12) 0.0450(12) -0.0015(10) -0.0049(8) -0.0003(9) C29 0.0617(15) 0.049(2) 0.0551(14) -0.0072(11) -0.0086(11) -0.0007(12) C30 0.074(2) 0.045(2) 0.092(2) -0.0172(15) -0.0260(15) -0.0025(14) C31 0.067(2) 0.042(2) 0.124(3) 0.007(2) -0.015(2) -0.0127(13) C32 0.100(2) 0.054(2) 0.087(2) 0.020(2) 0.012(2) -0.016(2) C33 0.074(2) 0.0447(15) 0.0537(14) 0.0044(11) 0.0082(11) -0.0089(12) C34 0.0256(10) 0.0397(13) 0.0489(12) -0.0033(10) 0.0008(8) -0.0033(9) C35 0.0587(15) 0.062(2) 0.0607(15) -0.0052(12) 0.0127(11) 0.0119(13) C36 0.063(2) 0.061(2) 0.103(2) -0.015(2) 0.034(2) 0.0080(15) C37 0.0314(13) 0.044(2) 0.134(3) 0.002(2) 0.0069(15) 0.0015(11) C38 0.0495(14) 0.045(2) 0.096(2) 0.0092(14) -0.0232(13) -0.0015(12) C39 0.0508(13) 0.0434(14) 0.0577(14) 0.0002(11) -0.0107(10) 0.0007(11) C40 0.0265(10) 0.0392(12) 0.0523(12) 0.0031(9) 0.0001(9) 0.0002(9) C41 0.0332(12) 0.060(2) 0.074(2) -0.0063(12) 0.0162(11) 0.0010(11) C42 0.0369(14) 0.069(2) 0.114(2) 0.002(2) 0.0260(14) 0.0062(13) C43 0.0274(13) 0.069(2) 0.143(3) 0.023(2) -0.002(2) 0.0011(13) C44 0.0427(14) 0.061(2) 0.095(2) 0.0228(14) -0.0265(14) -0.0066(12) C45 0.0367(12) 0.0497(15) 0.0607(14) 0.0139(11) -0.0118(10) -0.0057(10) _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 O1 C9 1.197(2) . yes C1 C9 1.567(2) . yes C1 C10 1.569(2) . yes C1 C8A 1.570(3) . yes C1 C2 1.583(2) . yes C2 C3 1.338(2) . yes C2 C14 1.539(2) . yes C3 C4 1.510(2) . yes C3 H3 0.95 . ? C4 C9 1.540(2) . yes C4 C4A 1.560(3) . yes C4 C18 1.565(2) . yes C4A C5 1.391(3) . yes C4A C8A 1.432(2) . yes C5 C6 1.409(3) . yes C5 C22 1.496(2) . yes C6 C7 1.398(2) . yes C6 C28 1.491(3) . yes C7 C8 1.406(3) . yes C7 C34 1.500(3) . yes C8 C8A 1.407(3) . yes C8 C40 1.507(2) . yes C10 C11 1.542(2) . yes C10 C13 1.544(3) . yes C10 C12 1.549(3) . yes C11 H11A 0.98 . ? C11 H11B 0.98 . ? C11 H11C 0.98 . ? C12 H12A 0.98 . ? C12 H12B 0.98 . ? C12 H12C 0.98 . ? C13 H13A 0.98 . ? C13 H13B 0.98 . ? C13 H13C 0.98 . ? C14 C16 1.526(3) . yes C14 C15 1.532(3) . yes C14 C17 1.540(3) . yes C15 H15A 0.98 . ? C15 H15B 0.98 . ? C15 H15C 0.98 . ? C16 H16A 0.98 . ? C16 H16B 0.98 . ? C16 H16C 0.98 . ? C17 H17A 0.98 . ? C17 H17B 0.98 . ? C17 H17C 0.98 . ? C18 C20 1.533(3) . yes C18 C19 1.538(3) . yes C18 C21 1.541(3) . yes C19 H19A 0.98 . ? C19 H19B 0.98 . ? C19 H19C 0.98 . ? C20 H20A 0.98 . ? C20 H20B 0.98 . ? C20 H20C 0.98 . ? C21 H21A 0.98 . ? C21 H21B 0.98 . ? C21 H21C 0.98 . ? C22 C27 1.385(3) . yes C22 C23 1.390(3) . yes C23 C24 1.384(3) . yes C23 H23 0.95 . ? C24 C25 1.375(3) . yes C24 H24 0.95 . ? C25 C26 1.375(3) . yes C25 H25 0.95 . ? C26 C27 1.386(3) . yes C26 H26 0.95 . ? C27 H27 0.95 . ? C28 C33 1.376(3) . yes C28 C29 1.384(3) . yes C29 C30 1.381(3) . yes C29 H29 0.95 . ? C30 C31 1.362(4) . yes C30 H30 0.95 . ? C31 C32 1.355(4) . yes C31 H31 0.95 . ? C32 C33 1.376(3) . yes C32 H32 0.95 . ? C33 H33 0.95 . ? C34 C39 1.382(3) . yes C34 C35 1.383(3) . yes C35 C36 1.393(3) . yes C35 H35 0.95 . ? C36 C37 1.356(4) . yes C36 H36 0.95 . ? C37 C38 1.360(4) . yes C37 H37 0.95 . ? C38 C39 1.378(3) . yes C38 H38 0.95 . ? C39 H39 0.95 . ? C40 C45 1.378(3) . yes C40 C41 1.394(3) . yes C41 C42 1.378(3) . yes C41 H41 0.95 . ? C42 C43 1.368(4) . yes C42 H42 0.95 . ? C43 C44 1.373(4) . yes C43 H43 0.95 . ? C44 C45 1.392(3) . yes C44 H44 0.95 . ? C45 H45 0.95 . ? 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 C9 C1 C10 109.25(14) . . yes C9 C1 C8A 92.14(13) . . yes C10 C1 C8A 123.9(2) . . yes C9 C1 C2 96.19(13) . . yes C10 C1 C2 122.0(2) . . yes C8A C1 C2 105.42(13) . . yes C3 C2 C14 122.3(2) . . yes C3 C2 C1 106.52(15) . . yes C14 C2 C1 130.4(2) . . yes C2 C3 C4 113.4(2) . . yes C2 C3 H3 123.30(11) . . ? C4 C3 H3 123.30(9) . . ? C3 C4 C9 95.84(14) . . yes C3 C4 C4A 104.83(13) . . yes C9 C4 C4A 93.55(13) . . yes C3 C4 C18 116.62(15) . . yes C9 C4 C18 113.30(14) . . yes C4A C4 C18 126.4(2) . . yes C5 C4A C8A 120.9(2) . . yes C5 C4A C4 131.0(2) . . yes C8A C4A C4 108.0(2) . . yes C4A C5 C6 118.7(2) . . yes C4A C5 C22 124.1(2) . . yes C6 C5 C22 116.6(2) . . yes C7 C6 C5 120.4(2) . . yes C7 C6 C28 119.6(2) . . yes C5 C6 C28 120.0(2) . . yes C6 C7 C8 121.0(2) . . yes C6 C7 C34 118.3(2) . . yes C8 C7 C34 120.6(2) . . yes C7 C8 C8A 119.0(2) . . yes C7 C8 C40 115.5(2) . . yes C8A C8 C40 125.5(2) . . yes C8 C8A C4A 119.2(2) . . yes C8 C8A C1 133.1(2) . . yes C4A C8A C1 107.66(15) . . yes O1 C9 C4 129.4(2) . . yes O1 C9 C1 129.8(2) . . yes C4 C9 C1 100.69(14) . . yes C11 C10 C13 107.3(2) . . yes C11 C10 C12 106.4(2) . . yes C13 C10 C12 107.7(2) . . yes C11 C10 C1 116.74(14) . . yes C13 C10 C1 109.5(2) . . yes C12 C10 C1 108.9(2) . . yes C10 C11 H11A 109.47(10) . . ? C10 C11 H11B 109.47(11) . . ? H11A C11 H11B 109.5 . . ? C10 C11 H11C 109.47(10) . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C10 C12 H12A 109.47(10) . . ? C10 C12 H12B 109.47(10) . . ? H12A C12 H12B 109.5 . . ? C10 C12 H12C 109.47(10) . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C10 C13 H13A 109.47(10) . . ? C10 C13 H13B 109.47(10) . . ? H13A C13 H13B 109.5 . . ? C10 C13 H13C 109.47(11) . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C16 C14 C15 110.6(2) . . yes C16 C14 C2 109.5(2) . . yes C15 C14 C2 114.9(2) . . yes C16 C14 C17 106.5(2) . . yes C15 C14 C17 105.7(2) . . yes C2 C14 C17 109.22(15) . . yes C14 C15 H15A 109.47(11) . . ? C14 C15 H15B 109.47(10) . . ? H15A C15 H15B 109.5 . . ? C14 C15 H15C 109.47(12) . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C14 C16 H16A 109.47(11) . . ? C14 C16 H16B 109.47(12) . . ? H16A C16 H16B 109.5 . . ? C14 C16 H16C 109.47(11) . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C14 C17 H17A 109.47(12) . . ? C14 C17 H17B 109.47(11) . . ? H17A C17 H17B 109.5 . . ? C14 C17 H17C 109.47(10) . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C20 C18 C19 109.2(2) . . yes C20 C18 C21 109.6(2) . . yes C19 C18 C21 104.7(2) . . yes C20 C18 C4 110.59(15) . . yes C19 C18 C4 115.0(2) . . yes C21 C18 C4 107.5(2) . . yes C18 C19 H19A 109.47(10) . . ? C18 C19 H19B 109.47(10) . . ? H19A C19 H19B 109.5 . . ? C18 C19 H19C 109.47(11) . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C18 C20 H20A 109.47(10) . . ? C18 C20 H20B 109.47(11) . . ? H20A C20 H20B 109.5 . . ? C18 C20 H20C 109.47(11) . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C18 C21 H21A 109.47(10) . . ? C18 C21 H21B 109.47(10) . . ? H21A C21 H21B 109.5 . . ? C18 C21 H21C 109.47(10) . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C27 C22 C23 118.9(2) . . yes C27 C22 C5 117.6(2) . . yes C23 C22 C5 123.2(2) . . yes C24 C23 C22 119.8(2) . . yes C24 C23 H23 120.08(13) . . ? C22 C23 H23 120.08(11) . . ? C25 C24 C23 120.7(2) . . yes C25 C24 H24 119.66(13) . . ? C23 C24 H24 119.66(13) . . ? C24 C25 C26 120.0(2) . . yes C24 C25 H25 119.98(13) . . ? C26 C25 H25 119.98(13) . . ? C25 C26 C27 119.6(2) . . yes C25 C26 H26 120.20(13) . . ? C27 C26 H26 120.20(13) . . ? C22 C27 C26 121.0(2) . . yes C22 C27 H27 119.52(11) . . ? C26 C27 H27 119.52(13) . . ? C33 C28 C29 117.4(2) . . yes C33 C28 C6 122.8(2) . . yes C29 C28 C6 119.7(2) . . yes C30 C29 C28 121.3(2) . . yes C30 C29 H29 119.3(2) . . ? C28 C29 H29 119.34(13) . . ? C31 C30 C29 120.1(3) . . yes C31 C30 H30 120.0(2) . . ? C29 C30 H30 120.0(2) . . ? C32 C31 C30 119.2(3) . . yes C32 C31 H31 120.4(2) . . ? C30 C31 H31 120.4(2) . . ? C31 C32 C33 121.3(3) . . yes C31 C32 H32 119.3(2) . . ? C33 C32 H32 119.3(2) . . ? C32 C33 C28 120.7(2) . . yes C32 C33 H33 119.7(2) . . ? C28 C33 H33 119.66(13) . . ? C39 C34 C35 117.5(2) . . yes C39 C34 C7 121.2(2) . . yes C35 C34 C7 121.2(2) . . yes C34 C35 C36 120.8(2) . . yes C34 C35 H35 119.62(13) . . ? C36 C35 H35 119.6(2) . . ? C37 C36 C35 120.3(2) . . yes C37 C36 H36 119.9(2) . . ? C35 C36 H36 119.9(2) . . ? C36 C37 C38 119.8(2) . . yes C36 C37 H37 120.1(2) . . ? C38 C37 H37 120.1(2) . . ? C37 C38 C39 120.5(2) . . yes C37 C38 H38 119.7(2) . . ? C39 C38 H38 119.7(2) . . ? C38 C39 C34 121.1(2) . . yes C38 C39 H39 119.4(2) . . ? C34 C39 H39 119.45(13) . . ? C45 C40 C41 118.2(2) . . yes C45 C40 C8 119.5(2) . . yes C41 C40 C8 122.0(2) . . yes C42 C41 C40 120.9(2) . . yes C42 C41 H41 119.6(2) . . ? C40 C41 H41 119.57(12) . . ? C43 C42 C41 120.0(2) . . yes C43 C42 H42 120.0(2) . . ? C41 C42 H42 120.0(2) . . ? C42 C43 C44 120.2(2) . . yes C42 C43 H43 119.9(2) . . ? C44 C43 H43 119.9(2) . . ? C43 C44 C45 119.9(2) . . yes C43 C44 H44 120.1(2) . . ? C45 C44 H44 120.1(2) . . ? C40 C45 C44 120.6(2) . . yes C40 C45 H45 119.69(12) . . ? C44 C45 H45 119.7(2) . . ? _cod_database_code 5000396