#------------------------------------------------------------------------------ #$Date: 2019-10-12 03:03:16 +0300 (Sat, 12 Oct 2019) $ #$Revision: 219301 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/12/43/7124301.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_7124301 loop_ _publ_author_name 'Xu, Kai' 'Liu, Hao' 'Hou, Yilin' 'Shen, Jiefeng' 'Liu, Delong' 'Zhang, Wanbin' _publ_section_title ; Pd-Catalyzed Asymmetric Allylic Substitution Cascade via An Asymmetric Desymmetrization for the Synthesis of Bicyclic Dihydrofurans ; _journal_name_full 'Chemical Communications' _journal_paper_doi 10.1039/C9CC07204G _journal_year 2019 _chemical_absolute_configuration ad _chemical_formula_moiety 'C15 H17 N O' _chemical_formula_sum 'C15 H17 N O' _chemical_formula_weight 227.29 _space_group_crystal_system orthorhombic _space_group_IT_number 19 _space_group_name_Hall 'P 2ac 2ab' _space_group_name_H-M_alt 'P 21 21 21' _symmetry_space_group_name_Hall 'P 2ac 2ab' _symmetry_space_group_name_H-M 'P 21 21 21' _atom_sites_solution_hydrogens geom _audit_block_doi 10.5517/ccdc.csd.cc2396rd _audit_creation_method SHELXL-2018/3 _audit_update_record ; 2019-08-05 deposited with the CCDC. 2019-10-11 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 5.93000(10) _cell_length_b 8.7765(2) _cell_length_c 24.7421(6) _cell_measurement_reflns_used 7455 _cell_measurement_temperature 297(2) _cell_measurement_theta_max 68.02 _cell_measurement_theta_min 3.57 _cell_volume 1287.69(5) _computing_structure_refinement 'SHELXL-2018/3 (Sheldrick, 2018)' _computing_structure_solution 'SHELXT 2014/5 (Sheldrick, 2014)' _diffrn_ambient_temperature 297(2) _diffrn_measured_fraction_theta_full 0.994 _diffrn_measured_fraction_theta_max 0.994 _diffrn_measurement_device_type 'Bruker D8 Venture' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54178 _diffrn_reflns_av_R_equivalents 0.0433 _diffrn_reflns_av_unetI/netI 0.0224 _diffrn_reflns_Laue_measured_fraction_full 0.994 _diffrn_reflns_Laue_measured_fraction_max 0.994 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_number 18841 _diffrn_reflns_point_group_measured_fraction_full 0.996 _diffrn_reflns_point_group_measured_fraction_max 0.995 _diffrn_reflns_theta_full 67.679 _diffrn_reflns_theta_max 68.308 _diffrn_reflns_theta_min 3.573 _exptl_absorpt_coefficient_mu 0.571 _exptl_crystal_colour coulorless _exptl_crystal_density_diffrn 1.172 _exptl_crystal_description block _exptl_crystal_F_000 488 _exptl_crystal_size_max 0.200 _exptl_crystal_size_mid 0.180 _exptl_crystal_size_min 0.160 _exptl_transmission_factor_max 0.7531 _exptl_transmission_factor_min 0.6789 _refine_diff_density_max 0.103 _refine_diff_density_min -0.142 _refine_diff_density_rms 0.026 _refine_ls_abs_structure_details ; Flack x determined using 825 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). ; _refine_ls_abs_structure_Flack -0.16(12) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.046 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 154 _refine_ls_number_reflns 2353 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.046 _refine_ls_R_factor_all 0.0424 _refine_ls_R_factor_gt 0.0387 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0619P)^2^+0.0791P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1033 _refine_ls_wR_factor_ref 0.1079 _reflns_Friedel_coverage 0.681 _reflns_Friedel_fraction_full 0.999 _reflns_Friedel_fraction_max 0.997 _reflns_number_gt 2161 _reflns_number_total 2353 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file c9cc07204g2.cif _cod_data_source_block b_a _cod_depositor_comments ; The following automatic conversions were performed: '_chemical_absolute_configuration' value 'AD' changed to 'ad' according to /home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26. Automatic conversion script Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas ; _cod_database_code 7124301 _shelx_shelxl_version_number 2018/3 _shelx_space_group_comment ; The symmetry employed for this shelxl refinement is uniquely defined by the following loop, which should always be used as a source of symmetry information in preference to the above space-group names. They are only intended as comments. ; _shelx_estimated_absorpt_t_min 0.894 _shelx_estimated_absorpt_t_max 0.914 _shelx_res_file ; TITL b_a.res in P2(1)2(1)2(1) b_a.res created by SHELXL-2018/3 at 17:47:44 on 29-Jul-2019 REM Old TITL b in P2(1)2(1)2(1) REM SHELXT solution in P2(1)2(1)2(1) REM R1 0.161, Rweak 0.035, Alpha 0.010, Orientation as input REM Flack x = -0.019 ( 0.121 ) from Parsons' quotients REM Formula found by SHELXT: C14 N2 O CELL 1.54178 5.9300 8.7765 24.7421 90.000 90.000 90.000 ZERR 4.000 0.0001 0.0002 0.0006 0.000 0.000 0.000 LATT -1 SYMM 1/2-X, -Y, 1/2+Z SYMM -X, 1/2+Y, 1/2-Z SYMM 1/2+X, 1/2-Y, -Z SFAC C H N O UNIT 60 68 4 4 TEMP 24.070 L.S. 10 ACTA SIZE 0.2 0.18 0.16 CONF BOND $H LIST 6 FMAP 2 PLAN 20 WGHT 0.061900 0.079100 FVAR 1.41541 O1 4 0.456989 0.498382 0.652475 11.00000 0.06523 0.08086 = 0.05696 0.00432 0.01013 -0.00756 N1 3 0.978366 0.613367 0.526334 11.00000 0.08712 0.10014 = 0.08038 0.02051 0.02536 0.00368 C1 1 0.700534 0.334391 0.601482 11.00000 0.06323 0.06064 = 0.05905 0.01102 0.00488 -0.01044 C2 1 0.702268 0.220424 0.562911 11.00000 0.11755 0.07762 = 0.06348 0.00471 0.00117 0.00541 AFIX 43 H2 2 0.586364 0.215016 0.537662 11.00000 -1.20000 AFIX 0 C3 1 0.873182 0.115302 0.561518 11.00000 0.15649 0.08481 = 0.08563 0.00909 0.02825 0.03338 AFIX 43 H3 2 0.873559 0.040094 0.535038 11.00000 -1.20000 AFIX 0 C4 1 1.043404 0.120404 0.598903 11.00000 0.09517 0.07636 = 0.15098 0.03544 0.03831 0.01983 AFIX 43 H4 2 1.161052 0.050480 0.597303 11.00000 -1.20000 AFIX 0 C5 1 1.039447 0.230003 0.639021 11.00000 0.07206 0.07461 = 0.15144 0.03137 -0.01845 -0.00712 AFIX 43 H5 2 1.152624 0.232297 0.665028 11.00000 -1.20000 AFIX 0 C7 1 0.520140 0.452656 0.599436 11.00000 0.05219 0.07389 = 0.05398 0.00128 -0.00208 -0.01037 AFIX 13 H7 2 0.387608 0.407438 0.582041 11.00000 -1.20000 AFIX 0 C6 1 0.867553 0.336090 0.640507 11.00000 0.07216 0.06442 = 0.09578 0.00892 -0.01800 -0.00909 AFIX 43 H6 2 0.864080 0.408862 0.667816 11.00000 -1.20000 AFIX 0 C8 1 0.577275 0.605921 0.569063 11.00000 0.05929 0.07542 = 0.05270 0.00987 -0.00221 0.00538 AFIX 13 H8 2 0.466989 0.619750 0.539976 11.00000 -1.20000 AFIX 0 C9 1 0.535654 0.729421 0.611897 11.00000 0.06471 0.06865 = 0.06873 0.00755 0.00275 0.01421 AFIX 13 H9 2 0.468118 0.820005 0.595333 11.00000 -1.20000 AFIX 0 C10 1 0.364115 0.648011 0.647563 11.00000 0.04876 0.10024 = 0.06685 -0.00320 0.00032 0.00775 AFIX 13 H10 2 0.220128 0.641729 0.628251 11.00000 -1.20000 AFIX 0 C11 1 0.324132 0.717514 0.702620 11.00000 0.06682 0.11956 = 0.07823 -0.01334 0.00980 0.01559 AFIX 23 H11A 2 0.240345 0.645842 0.724697 11.00000 -1.20000 H11B 2 0.232730 0.808452 0.698551 11.00000 -1.20000 AFIX 0 C12 1 0.541052 0.758883 0.731364 11.00000 0.08395 0.13583 = 0.07480 -0.03458 -0.00109 0.01811 AFIX 23 H12A 2 0.622249 0.666725 0.740832 11.00000 -1.20000 H12B 2 0.506496 0.813247 0.764478 11.00000 -1.20000 AFIX 0 C13 1 0.687535 0.857927 0.695332 11.00000 0.08246 0.10075 = 0.11992 -0.04554 -0.00338 0.00243 AFIX 23 H13A 2 0.607679 0.951047 0.686411 11.00000 -1.20000 H13B 2 0.824781 0.885213 0.714340 11.00000 -1.20000 AFIX 0 C14 1 0.746022 0.772646 0.643922 11.00000 0.06437 0.06850 = 0.09293 -0.00942 0.00887 -0.00451 AFIX 23 H14A 2 0.829018 0.680966 0.653071 11.00000 -1.20000 H14B 2 0.842631 0.835905 0.621621 11.00000 -1.20000 AFIX 0 C15 1 0.803980 0.609903 0.545161 11.00000 0.07497 0.06949 = 0.05639 0.01329 0.00911 0.00457 HKLF 4 REM b_a.res in P2(1)2(1)2(1) REM wR2 = 0.107888, GooF = S = 1.04555, Restrained GooF = 1.04555 for all data REM R1 = 0.038671 for 2161 Fo > 4sig(Fo) and 0.042389 for all 2353 data REM 154 parameters refined using 0 restraints END WGHT 0.0474 0.1026 REM Highest difference peak 0.103, deepest hole -0.142, 1-sigma level 0.026 Q1 1 0.8445 0.2582 0.5628 11.00000 0.05 0.10 Q2 1 0.6027 0.5090 0.6715 11.00000 0.05 0.09 Q3 1 0.6357 1.1122 0.6567 11.00000 0.05 0.08 Q4 1 0.9536 0.3450 0.6167 11.00000 0.05 0.08 Q5 1 1.1293 0.3242 0.6030 11.00000 0.05 0.07 Q6 1 1.1731 0.3407 0.6075 11.00000 0.05 0.07 Q7 1 0.7378 0.1729 0.6912 11.00000 0.05 0.07 Q8 1 0.8388 0.5747 0.6693 11.00000 0.05 0.07 Q9 1 0.7013 0.5743 0.6902 11.00000 0.05 0.07 Q10 1 1.2807 0.2570 0.6172 11.00000 0.05 0.07 Q11 1 0.6833 0.5979 0.7399 11.00000 0.05 0.07 Q12 1 0.8168 0.4470 0.6862 11.00000 0.05 0.07 Q13 1 1.0977 0.2408 0.6997 11.00000 0.05 0.07 Q14 1 0.5983 0.9591 0.6696 11.00000 0.05 0.07 Q15 1 1.0352 0.4192 0.6041 11.00000 0.05 0.06 Q16 1 0.8051 0.3600 0.6083 11.00000 0.05 0.06 Q17 1 0.9416 0.4675 0.6475 11.00000 0.05 0.06 Q18 1 0.6472 0.4013 0.6016 11.00000 0.05 0.06 Q19 1 0.4992 0.5217 0.7168 11.00000 0.05 0.06 Q20 1 0.8181 0.5521 0.6394 11.00000 0.05 0.06 ; _shelx_res_checksum 15534 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' 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_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp O1 O 0.4570(3) 0.49838(18) 0.65247(6) 0.0677(4) Uani 1 1 d . . N1 N 0.9784(4) 0.6134(3) 0.52633(9) 0.0892(7) Uani 1 1 d . . C1 C 0.7005(4) 0.3344(2) 0.60148(8) 0.0610(5) Uani 1 1 d . . C2 C 0.7023(6) 0.2204(3) 0.56291(10) 0.0862(8) Uani 1 1 d . . H2 H 0.586364 0.215016 0.537662 0.103 Uiso 1 1 calc R U C3 C 0.8732(8) 0.1153(4) 0.56152(14) 0.1090(11) Uani 1 1 d . . H3 H 0.873559 0.040094 0.535038 0.131 Uiso 1 1 calc R U C4 C 1.0434(6) 0.1204(4) 0.59890(17) 0.1075(12) Uani 1 1 d . . H4 H 1.161052 0.050480 0.597303 0.129 Uiso 1 1 calc R U C5 C 1.0394(5) 0.2300(3) 0.63902(17) 0.0994(10) Uani 1 1 d . . H5 H 1.152624 0.232297 0.665028 0.119 Uiso 1 1 calc R U C7 C 0.5201(3) 0.4527(3) 0.59944(8) 0.0600(5) Uani 1 1 d . . H7 H 0.387608 0.407438 0.582041 0.072 Uiso 1 1 calc R U C6 C 0.8676(4) 0.3361(3) 0.64051(12) 0.0775(7) Uani 1 1 d . . H6 H 0.864080 0.408862 0.667816 0.093 Uiso 1 1 calc R U C8 C 0.5773(4) 0.6059(3) 0.56906(8) 0.0625(5) Uani 1 1 d . . H8 H 0.466989 0.619750 0.539976 0.075 Uiso 1 1 calc R U C9 C 0.5357(4) 0.7294(3) 0.61190(9) 0.0674(6) Uani 1 1 d . . H9 H 0.468118 0.820005 0.595333 0.081 Uiso 1 1 calc R U C10 C 0.3641(4) 0.6480(3) 0.64756(10) 0.0719(6) Uani 1 1 d . . H10 H 0.220128 0.641729 0.628251 0.086 Uiso 1 1 calc R U C11 C 0.3241(5) 0.7175(4) 0.70262(11) 0.0882(8) Uani 1 1 d . . H11A H 0.240345 0.645842 0.724697 0.106 Uiso 1 1 calc R U H11B H 0.232730 0.808452 0.698551 0.106 Uiso 1 1 calc R U C12 C 0.5411(5) 0.7589(4) 0.73136(12) 0.0982(10) Uani 1 1 d . . H12A H 0.622249 0.666725 0.740832 0.118 Uiso 1 1 calc R U H12B H 0.506496 0.813247 0.764478 0.118 Uiso 1 1 calc R U C13 C 0.6875(6) 0.8579(4) 0.69533(14) 0.1010(10) Uani 1 1 d . . H13A H 0.607679 0.951047 0.686411 0.121 Uiso 1 1 calc R U H13B H 0.824781 0.885213 0.714340 0.121 Uiso 1 1 calc R U C14 C 0.7460(4) 0.7726(3) 0.64392(12) 0.0753(6) Uani 1 1 d . . H14A H 0.829018 0.680966 0.653071 0.090 Uiso 1 1 calc R U H14B H 0.842631 0.835905 0.621621 0.090 Uiso 1 1 calc R U C15 C 0.8040(4) 0.6099(3) 0.54516(9) 0.0670(6) Uani 1 1 d . . 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 0.0652(8) 0.0809(9) 0.0570(8) 0.0043(7) 0.0101(7) -0.0076(8) N1 0.0871(15) 0.1001(16) 0.0804(13) 0.0205(12) 0.0254(12) 0.0037(13) C1 0.0632(12) 0.0606(11) 0.0590(11) 0.0110(9) 0.0049(9) -0.0104(9) C2 0.118(2) 0.0776(15) 0.0635(14) 0.0047(12) 0.0012(14) 0.0054(16) C3 0.156(3) 0.0848(18) 0.0856(19) 0.0091(16) 0.028(2) 0.033(2) C4 0.095(2) 0.0764(17) 0.151(3) 0.035(2) 0.038(2) 0.0198(16) C5 0.0721(15) 0.0746(15) 0.151(3) 0.0314(19) -0.0184(18) -0.0071(14) C7 0.0522(10) 0.0739(12) 0.0540(10) 0.0013(9) -0.0021(9) -0.0104(9) C6 0.0722(14) 0.0644(12) 0.0958(17) 0.0089(12) -0.0180(13) -0.0091(11) C8 0.0593(11) 0.0754(13) 0.0527(10) 0.0099(10) -0.0022(8) 0.0054(10) C9 0.0647(12) 0.0686(12) 0.0687(13) 0.0076(10) 0.0027(10) 0.0142(10) C10 0.0488(10) 0.1002(17) 0.0669(13) -0.0032(12) 0.0003(9) 0.0078(11) C11 0.0668(14) 0.120(2) 0.0782(16) -0.0133(15) 0.0098(12) 0.0156(15) C12 0.0839(17) 0.136(3) 0.0748(16) -0.0346(16) -0.0011(14) 0.0181(18) C13 0.0825(17) 0.101(2) 0.120(2) -0.0455(18) -0.0034(17) 0.0024(17) C14 0.0644(13) 0.0685(12) 0.0929(17) -0.0094(13) 0.0089(12) -0.0045(10) C15 0.0750(14) 0.0695(13) 0.0564(11) 0.0133(10) 0.0091(11) 0.0046(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 C7 O1 C10 106.39(17) C2 C1 C6 119.0(2) C2 C1 C7 119.0(2) C6 C1 C7 122.0(2) C3 C2 C1 120.6(3) C3 C2 H2 119.7 C1 C2 H2 119.7 C4 C3 C2 120.4(3) C4 C3 H3 119.8 C2 C3 H3 119.8 C3 C4 C5 119.7(3) C3 C4 H4 120.2 C5 C4 H4 120.2 C6 C5 C4 120.0(3) C6 C5 H5 120.0 C4 C5 H5 120.0 O1 C7 C1 110.72(17) O1 C7 C8 104.80(17) C1 C7 C8 117.10(17) O1 C7 H7 108.0 C1 C7 H7 108.0 C8 C7 H7 108.0 C5 C6 C1 120.2(3) C5 C6 H6 119.9 C1 C6 H6 119.9 C15 C8 C9 114.1(2) C15 C8 C7 114.11(18) C9 C8 C7 103.80(16) C15 C8 H8 108.2 C9 C8 H8 108.2 C7 C8 H8 108.2 C10 C9 C14 111.19(19) C10 C9 C8 100.13(18) C14 C9 C8 113.73(19) C10 C9 H9 110.5 C14 C9 H9 110.5 C8 C9 H9 110.5 O1 C10 C11 110.8(2) O1 C10 C9 102.87(17) C11 C10 C9 115.9(2) O1 C10 H10 109.0 C11 C10 H10 109.0 C9 C10 H10 109.0 C10 C11 C12 112.8(2) C10 C11 H11A 109.0 C12 C11 H11A 109.0 C10 C11 H11B 109.0 C12 C11 H11B 109.0 H11A C11 H11B 107.8 C11 C12 C13 110.3(3) C11 C12 H12A 109.6 C13 C12 H12A 109.6 C11 C12 H12B 109.6 C13 C12 H12B 109.6 H12A C12 H12B 108.1 C14 C13 C12 109.9(2) C14 C13 H13A 109.7 C12 C13 H13A 109.7 C14 C13 H13B 109.7 C12 C13 H13B 109.7 H13A C13 H13B 108.2 C13 C14 C9 111.8(2) C13 C14 H14A 109.3 C9 C14 H14A 109.3 C13 C14 H14B 109.3 C9 C14 H14B 109.3 H14A C14 H14B 107.9 N1 C15 C8 179.5(3) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance O1 C7 1.422(3) O1 C10 1.429(3) N1 C15 1.135(3) C1 C2 1.383(3) C1 C6 1.383(3) C1 C7 1.491(3) C2 C3 1.371(5) C2 H2 0.9300 C3 C4 1.370(6) C3 H3 0.9300 C4 C5 1.382(5) C4 H4 0.9300 C5 C6 1.381(4) C5 H5 0.9300 C7 C8 1.578(3) C7 H7 0.9800 C6 H6 0.9300 C8 C15 1.469(3) C8 C9 1.536(3) C8 H8 0.9800 C9 C10 1.524(3) C9 C14 1.526(3) C9 H9 0.9800 C10 C11 1.511(3) C10 H10 0.9800 C11 C12 1.514(4) C11 H11A 0.9700 C11 H11B 0.9700 C12 C13 1.518(5) C12 H12A 0.9700 C12 H12B 0.9700 C13 C14 1.516(4) C13 H13A 0.9700 C13 H13B 0.9700 C14 H14A 0.9700 C14 H14B 0.9700 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 C6 C1 C2 C3 -3.4(4) C7 C1 C2 C3 176.0(2) C1 C2 C3 C4 0.9(5) C2 C3 C4 C5 1.6(5) C3 C4 C5 C6 -1.6(5) C10 O1 C7 C1 155.87(17) C10 O1 C7 C8 28.7(2) C2 C1 C7 O1 145.2(2) C6 C1 C7 O1 -35.5(3) C2 C1 C7 C8 -94.8(2) C6 C1 C7 C8 84.5(3) C4 C5 C6 C1 -0.9(4) C2 C1 C6 C5 3.4(4) C7 C1 C6 C5 -176.0(2) O1 C7 C8 C15 124.6(2) C1 C7 C8 C15 1.5(3) O1 C7 C8 C9 -0.2(2) C1 C7 C8 C9 -123.3(2) C15 C8 C9 C10 -150.60(19) C7 C8 C9 C10 -25.8(2) C15 C8 C9 C14 -31.9(3) C7 C8 C9 C14 92.9(2) C7 O1 C10 C11 -171.3(2) C7 O1 C10 C9 -46.8(2) C14 C9 C10 O1 -76.6(2) C8 C9 C10 O1 44.0(2) C14 C9 C10 C11 44.5(3) C8 C9 C10 C11 165.0(2) O1 C10 C11 C12 70.8(3) C9 C10 C11 C12 -45.9(3) C10 C11 C12 C13 52.8(3) C11 C12 C13 C14 -60.3(3) C12 C13 C14 C9 60.3(3) C10 C9 C14 C13 -51.3(3) C8 C9 C14 C13 -163.4(2)