#------------------------------------------------------------------------------ #$Date: 2020-03-04 09:43:11 +0200 (Wed, 04 Mar 2020) $ #$Revision: 248751 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/55/74/1557448.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_1557448 loop_ _publ_author_name 'Lei, Guangyue' 'Zhang, Hanwen' 'Chen, Bin' 'Xu, Meichen' 'Zhang, Guozhu' _publ_section_title ; Copper-catalyzed enantioselective arylalkynylation of alkenes ; _journal_issue 6 _journal_name_full 'Chemical Science' _journal_page_first 1623 _journal_paper_doi 10.1039/C9SC04029C _journal_volume 11 _journal_year 2020 _chemical_absolute_configuration unk _chemical_formula_sum 'C26 H26' _chemical_formula_weight 338.47 _space_group_crystal_system monoclinic _space_group_IT_number 4 _space_group_name_Hall 'P 2yb' _space_group_name_H-M_alt 'P 1 21 1' _atom_sites_solution_hydrogens geom _audit_creation_method SHELXL-2013 _audit_update_record ; 2019-04-05 deposited with the CCDC. 2019-11-26 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 104.61(2) _cell_angle_gamma 90 _cell_formula_units_Z 2 _cell_length_a 9.423(7) _cell_length_b 10.032(6) _cell_length_c 11.391(7) _cell_measurement_reflns_used 2851 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 54.685 _cell_measurement_theta_min 4.467 _cell_volume 1042.0(12) _computing_cell_refinement 'Bruker SAINT' _computing_data_collection 'Bruker APEX2' _computing_data_reduction 'Bruker SAINT' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _computing_structure_refinement 'SHELXL-2013 (Sheldrick, 2013)' _computing_structure_solution 'SHELXS-97 (Sheldrick 2008)' _diffrn_ambient_temperature 293(2) _diffrn_measured_fraction_theta_full 0.959 _diffrn_measured_fraction_theta_max 0.987 _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0520 _diffrn_reflns_av_unetI/netI 0.0629 _diffrn_reflns_Laue_measured_fraction_full 0.959 _diffrn_reflns_Laue_measured_fraction_max 0.987 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_number 9901 _diffrn_reflns_point_group_measured_fraction_full 0.940 _diffrn_reflns_point_group_measured_fraction_max 0.969 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 24.996 _diffrn_reflns_theta_min 2.514 _exptl_absorpt_coefficient_mu 0.061 _exptl_absorpt_correction_T_max 0.7456 _exptl_absorpt_correction_T_min 0.5795 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details sadabs _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.079 _exptl_crystal_description prismatic _exptl_crystal_F_000 364 _exptl_crystal_size_max 0.200 _exptl_crystal_size_mid 0.150 _exptl_crystal_size_min 0.100 _refine_diff_density_max 0.208 _refine_diff_density_min -0.155 _refine_diff_density_rms 0.032 _refine_ls_abs_structure_details ; Flack x determined using 810 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons and Flack (2004), Acta Cryst. A60, s61). ; _refine_ls_abs_structure_Flack 2.3(10) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method SHELXL _refine_ls_goodness_of_fit_ref 1.046 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 269 _refine_ls_number_reflns 3551 _refine_ls_number_restraints 55 _refine_ls_restrained_S_all 1.103 _refine_ls_R_factor_all 0.1028 _refine_ls_R_factor_gt 0.0628 _refine_ls_shift/su_max 0.003 _refine_ls_shift/su_mean 0.001 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0974P)^2^+0.0743P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1624 _refine_ls_wR_factor_ref 0.1939 _reflns_Friedel_coverage 0.846 _reflns_Friedel_fraction_full 0.919 _reflns_Friedel_fraction_max 0.948 _reflns_number_gt 2326 _reflns_number_total 3551 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file c9sc04029c2.cif _cod_data_source_block mo_d8v19247_0m _cod_original_cell_volume 1042.1(12) _cod_original_sg_symbol_H-M 'P 21' _cod_database_code 1557448 _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 0.988 _shelx_estimated_absorpt_t_max 0.994 _shelxl_version_number 2013-4 _shelx_res_file ; TITL mo_d8v19247_0m_a.res in P2(1) CELL 0.71073 9.4233 10.0324 11.3907 90 104.607 90 ZERR 2 0.0069 0.0059 0.007 0 0.021 0 LATT -1 SYMM -X,0.5+Y,-Z SFAC C H UNIT 52 52 OMIT 0 0 1 OMIT 2 1 1 OMIT 2 -1 0 OMIT 3 -3 4 OMIT 3 0 3 OMIT 3 3 4 OMIT -3.00 50.00 L.S. 10 ACTA BOND $H FMAP 2 PLAN 20 LIST 4 simu 0.004 c24 c25 c26 c2 c3 c4 c24' c25' c26' dfix 1.55 0.02 c23 c24 c23 c25 c23 c26 c23 c24' c23 c25' c23 c26' size 0.20 0.15 0.10 wpdb -1 mpla c1 > c6 mpla c11 > c16 mpla c17 > c22 htab conf TEMP 20.29 WGHT 0.097400 0.074300 EXTI 0.082297 FVAR 1.77947 C1 1 0.253002 0.402067 0.365612 11.00000 0.08023 0.13843 = 0.09857 -0.00381 0.03563 -0.00900 AFIX 43 H1 2 0.288608 0.347282 0.432414 11.00000 -1.20000 AFIX 0 C2 1 0.110268 0.389115 0.299106 11.00000 0.07780 0.18475 = 0.15463 -0.04645 0.03414 -0.02347 AFIX 43 H2 2 0.048165 0.327979 0.322134 11.00000 -1.20000 AFIX 0 C3 1 0.059824 0.467983 0.197472 11.00000 0.07199 0.17974 = 0.14307 -0.05963 0.00985 0.00530 AFIX 43 H3 2 -0.036158 0.458649 0.151095 11.00000 -1.20000 AFIX 0 C4 1 0.149885 0.559099 0.165032 11.00000 0.08772 0.17385 = 0.11837 -0.04663 0.01325 0.02751 AFIX 43 H4 2 0.115539 0.612544 0.097087 11.00000 -1.20000 AFIX 0 C5 1 0.289600 0.571417 0.232218 11.00000 0.08151 0.10566 = 0.09114 -0.00870 0.02442 0.02169 AFIX 43 H5 2 0.350467 0.633168 0.208396 11.00000 -1.20000 AFIX 0 C6 1 0.344943 0.496811 0.333673 11.00000 0.06195 0.08723 = 0.06626 -0.02224 0.02520 -0.00004 C7 1 0.499736 0.511579 0.407263 11.00000 0.07507 0.09724 = 0.06825 -0.02014 0.02665 -0.00030 AFIX 23 H7A 2 0.502673 0.495084 0.491751 11.00000 -1.20000 H7B 2 0.530471 0.602987 0.400835 11.00000 -1.20000 AFIX 0 C8 1 0.610937 0.417581 0.369594 11.00000 0.06611 0.07332 = 0.05817 -0.00654 0.02025 -0.00863 AFIX 13 H8 2 0.575701 0.325881 0.371373 11.00000 -1.20000 AFIX 0 C9 1 0.619849 0.446658 0.245966 11.00000 0.05661 0.07770 = 0.05442 -0.00977 0.01165 0.00273 C10 1 0.627982 0.472197 0.146800 11.00000 0.05690 0.07696 = 0.05739 -0.00964 0.01020 0.00433 C11 1 0.646520 0.504585 0.028299 11.00000 0.05091 0.08705 = 0.05143 -0.00348 0.00974 0.00379 C12 1 0.627617 0.632953 -0.016231 11.00000 0.09634 0.08619 = 0.07370 -0.00141 0.01944 0.01197 AFIX 43 H12 2 0.594946 0.699365 0.027555 11.00000 -1.20000 AFIX 0 C13 1 0.657152 0.662447 -0.125351 11.00000 0.11280 0.10421 = 0.07879 0.02063 0.02197 0.00522 AFIX 43 H13 2 0.646041 0.749452 -0.154404 11.00000 -1.20000 AFIX 0 C14 1 0.702235 0.566422 -0.191123 11.00000 0.09996 0.12604 = 0.07530 0.00042 0.03355 -0.01514 AFIX 43 H14 2 0.722656 0.587643 -0.264640 11.00000 -1.20000 AFIX 0 C15 1 0.717337 0.441350 -0.150386 11.00000 0.09952 0.10002 = 0.08309 -0.00637 0.04548 -0.00029 AFIX 43 H15 2 0.747744 0.375708 -0.196300 11.00000 -1.20000 AFIX 0 C16 1 0.688689 0.407786 -0.041567 11.00000 0.08444 0.08254 = 0.07275 -0.00612 0.03288 -0.00356 AFIX 43 H16 2 0.697809 0.319730 -0.015213 11.00000 -1.20000 AFIX 0 C17 1 0.759452 0.428286 0.461181 11.00000 0.06738 0.06795 = 0.04943 -0.00159 0.01800 -0.00388 C18 1 0.851670 0.533568 0.461543 11.00000 0.07916 0.07926 = 0.07933 0.02269 0.00549 -0.01453 AFIX 43 H18 2 0.826488 0.597308 0.400540 11.00000 -1.20000 AFIX 0 C19 1 0.981045 0.547754 0.549972 11.00000 0.07797 0.07797 = 0.08919 0.01761 0.00631 -0.01354 AFIX 43 H19 2 1.039396 0.622116 0.548205 11.00000 -1.20000 AFIX 0 C20 1 1.026334 0.454959 0.640836 11.00000 0.06650 0.06740 = 0.05629 -0.00297 0.01095 0.00203 C21 1 0.936278 0.347208 0.638607 11.00000 0.09437 0.06514 = 0.05196 0.00503 0.01943 0.00177 AFIX 43 H21 2 0.963796 0.281243 0.697313 11.00000 -1.20000 AFIX 0 C22 1 0.804699 0.334322 0.550533 11.00000 0.07759 0.07338 = 0.05831 -0.00095 0.02366 -0.01159 AFIX 43 H22 2 0.745862 0.260264 0.552146 11.00000 -1.20000 AFIX 0 C23 1 1.169040 0.472136 0.739363 11.00000 0.07447 0.08036 = 0.07117 -0.00801 -0.00218 0.00545 PART 1 C24 1 1.292189 0.412944 0.703243 10.50000 0.08676 0.14707 = 0.10444 -0.01693 -0.00140 -0.00540 AFIX 137 H24A 2 1.317189 0.467303 0.642048 10.50000 -1.50000 H24B 2 1.265907 0.325254 0.671391 10.50000 -1.50000 H24C 2 1.374872 0.407151 0.772413 10.50000 -1.50000 AFIX 0 C25 1 1.156386 0.387943 0.856448 10.50000 0.11759 0.14507 = 0.08380 0.01263 -0.01139 0.00281 AFIX 137 H25A 2 1.161639 0.294463 0.840037 10.50000 -1.50000 H25B 2 1.064509 0.407284 0.874738 10.50000 -1.50000 H25C 2 1.235455 0.411827 0.924460 10.50000 -1.50000 AFIX 0 C26 1 1.177668 0.609860 0.792693 10.50000 0.11260 0.11996 = 0.10461 -0.01682 -0.01539 0.00017 AFIX 137 H26A 2 1.267749 0.619243 0.854316 10.50000 -1.50000 H26B 2 1.096287 0.623663 0.827780 10.50000 -1.50000 H26C 2 1.174478 0.674626 0.730039 10.50000 -1.50000 PART 2 AFIX 0 C24' 1 1.271717 0.348775 0.736647 10.50000 0.09715 0.11900 = 0.07709 0.01418 -0.00544 0.00781 AFIX 137 H24D 2 1.365560 0.363634 0.792113 10.50000 -1.50000 H24E 2 1.284082 0.337625 0.656109 10.50000 -1.50000 H24F 2 1.228050 0.269925 0.760065 10.50000 -1.50000 AFIX 0 C25' 1 1.141567 0.487258 0.859768 10.50000 0.11330 0.13414 = 0.07474 -0.02419 0.00653 0.00462 AFIX 137 H25D 2 1.095979 0.571940 0.864689 10.50000 -1.50000 H25E 2 1.232813 0.482604 0.920644 10.50000 -1.50000 H25F 2 1.077924 0.417129 0.872799 10.50000 -1.50000 AFIX 0 C26' 1 1.260518 0.597715 0.712749 10.50000 0.07830 0.11192 = 0.11009 0.00592 -0.00693 -0.02310 AFIX 137 H26D 2 1.200439 0.676168 0.704128 10.50000 -1.50000 H26E 2 1.290348 0.582810 0.639220 10.50000 -1.50000 H26F 2 1.345718 0.609601 0.778911 10.50000 -1.50000 PART 0 AFIX 0 HKLF 4 REM mo_d8v19247_0m_a.res in P2(1) REM R1 = 0.0628 for 2326 Fo > 4sig(Fo) and 0.1028 for all 3551 data REM 269 parameters refined using 55 restraints END WGHT 0.0798 0.1113 REM No hydrogen bonds found for HTAB generation REM Highest difference peak 0.208, deepest hole -0.155, 1-sigma level 0.032 Q1 1 0.0863 0.5191 0.1572 11.00000 0.05 0.21 Q2 1 0.0596 0.4402 0.2528 11.00000 0.05 0.18 Q3 1 1.2524 0.6061 0.6603 11.00000 0.05 0.15 Q4 1 1.2828 0.5038 0.6763 11.00000 0.05 0.13 Q5 1 -0.0667 0.4802 0.0211 11.00000 0.05 0.12 Q6 1 0.5203 0.4115 0.5284 11.00000 0.05 0.11 Q7 1 0.9017 0.4596 0.5578 11.00000 0.05 0.10 Q8 1 1.2262 0.6225 0.7381 11.00000 0.05 0.10 Q9 1 0.9158 0.3209 0.6029 11.00000 0.05 0.10 Q10 1 0.8211 0.4129 0.0625 11.00000 0.05 0.10 Q11 1 1.2715 0.5927 0.9260 11.00000 0.05 0.10 Q12 1 0.8580 0.3963 0.6150 11.00000 0.05 0.10 Q13 1 1.4660 0.2980 0.7753 11.00000 0.05 0.09 Q14 1 1.2783 0.7953 0.7301 11.00000 0.05 0.09 Q15 1 0.5420 0.7838 -0.1586 11.00000 0.05 0.09 Q16 1 1.0909 0.3535 0.7122 11.00000 0.05 0.09 Q17 1 1.0969 0.4590 0.6820 11.00000 0.05 0.09 Q18 1 0.5883 0.5183 -0.0402 11.00000 0.05 0.09 Q19 1 0.5251 0.3652 0.1603 11.00000 0.05 0.09 Q20 1 0.4823 0.5938 0.5491 11.00000 0.05 0.09 ; _shelx_res_checksum 89662 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, 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 _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.2530(7) 0.4021(8) 0.3656(6) 0.103(2) Uani 1 1 d . . . . . H1 H 0.2886 0.3473 0.4324 0.124 Uiso 1 1 calc R U . . . C2 C 0.1103(9) 0.3891(11) 0.2991(8) 0.138(3) Uani 1 1 d . U . . . H2 H 0.0482 0.3280 0.3221 0.166 Uiso 1 1 calc R U . . . C3 C 0.0598(9) 0.4680(11) 0.1975(8) 0.135(3) Uani 1 1 d . U . . . H3 H -0.0362 0.4586 0.1511 0.162 Uiso 1 1 calc R U . . . C4 C 0.1499(9) 0.5591(10) 0.1650(7) 0.129(3) Uani 1 1 d . U . . . H4 H 0.1155 0.6125 0.0971 0.155 Uiso 1 1 calc R U . . . C5 C 0.2896(7) 0.5714(7) 0.2322(6) 0.0923(18) Uani 1 1 d . . . . . H5 H 0.3505 0.6332 0.2084 0.111 Uiso 1 1 calc R U . . . C6 C 0.3449(6) 0.4968(5) 0.3337(4) 0.0702(14) Uani 1 1 d . . . . . C7 C 0.4997(6) 0.5116(6) 0.4073(4) 0.0786(15) Uani 1 1 d . . . . . H7A H 0.5027 0.4951 0.4918 0.094 Uiso 1 1 calc R U . . . H7B H 0.5305 0.6030 0.4008 0.094 Uiso 1 1 calc R U . . . C8 C 0.6109(5) 0.4176(5) 0.3696(4) 0.0650(12) Uani 1 1 d . . . . . H8 H 0.5757 0.3259 0.3714 0.078 Uiso 1 1 calc R U . . . C9 C 0.6198(5) 0.4467(5) 0.2460(4) 0.0633(12) Uani 1 1 d . . . . . C10 C 0.6280(5) 0.4722(5) 0.1468(4) 0.0645(12) Uani 1 1 d . . . . . C11 C 0.6465(5) 0.5046(5) 0.0283(4) 0.0637(13) Uani 1 1 d . . . . . C12 C 0.6276(7) 0.6330(6) -0.0162(5) 0.0858(17) Uani 1 1 d . . . . . H12 H 0.5949 0.6994 0.0276 0.103 Uiso 1 1 calc R U . . . C13 C 0.6572(8) 0.6624(7) -0.1254(5) 0.099(2) Uani 1 1 d . . . . . H13 H 0.6460 0.7495 -0.1544 0.119 Uiso 1 1 calc R U . . . C14 C 0.7022(8) 0.5664(8) -0.1911(6) 0.098(2) Uani 1 1 d . . . . . H14 H 0.7227 0.5876 -0.2646 0.118 Uiso 1 1 calc R U . . . C15 C 0.7173(7) 0.4414(7) -0.1504(5) 0.0902(18) Uani 1 1 d . . . . . H15 H 0.7477 0.3757 -0.1963 0.108 Uiso 1 1 calc R U . . . C16 C 0.6887(6) 0.4078(6) -0.0416(4) 0.0776(15) Uani 1 1 d . . . . . H16 H 0.6978 0.3197 -0.0152 0.093 Uiso 1 1 calc R U . . . C17 C 0.7595(5) 0.4283(5) 0.4612(3) 0.0610(12) Uani 1 1 d . . . . . C18 C 0.8517(6) 0.5336(6) 0.4615(5) 0.0818(16) Uani 1 1 d . . . . . H18 H 0.8265 0.5973 0.4005 0.098 Uiso 1 1 calc R U . . . C19 C 0.9810(6) 0.5478(6) 0.5500(5) 0.0844(16) Uani 1 1 d . . . . . H19 H 1.0394 0.6221 0.5482 0.101 Uiso 1 1 calc R U . . . C20 C 1.0263(5) 0.4550(5) 0.6408(4) 0.0642(12) Uani 1 1 d . . . . . C21 C 0.9363(6) 0.3472(5) 0.6386(4) 0.0703(14) Uani 1 1 d . . . . . H21 H 0.9638 0.2812 0.6973 0.084 Uiso 1 1 calc R U . . . C22 C 0.8047(6) 0.3343(5) 0.5505(4) 0.0686(13) Uani 1 1 d . . . . . H22 H 0.7459 0.2603 0.5521 0.082 Uiso 1 1 calc R U . . . C23 C 1.1690(6) 0.4721(5) 0.7394(5) 0.0790(15) Uani 1 1 d D . . . . C24 C 1.2922(19) 0.413(2) 0.7032(16) 0.117(4) Uani 0.5 1 d D U P A 1 H24A H 1.3172 0.4673 0.6420 0.176 Uiso 0.5 1 calc R U P A 1 H24B H 1.2659 0.3253 0.6714 0.176 Uiso 0.5 1 calc R U P A 1 H24C H 1.3749 0.4072 0.7724 0.176 Uiso 0.5 1 calc R U P A 1 C25 C 1.156(2) 0.388(2) 0.8564(13) 0.122(4) Uani 0.5 1 d D U P A 1 H25A H 1.1616 0.2945 0.8400 0.183 Uiso 0.5 1 calc R U P A 1 H25B H 1.0645 0.4073 0.8747 0.183 Uiso 0.5 1 calc R U P A 1 H25C H 1.2355 0.4118 0.9245 0.183 Uiso 0.5 1 calc R U P A 1 C26 C 1.1777(19) 0.6099(14) 0.7927(14) 0.120(4) Uani 0.5 1 d D U P A 1 H26A H 1.2677 0.6192 0.8543 0.180 Uiso 0.5 1 calc R U P A 1 H26B H 1.0963 0.6237 0.8278 0.180 Uiso 0.5 1 calc R U P A 1 H26C H 1.1745 0.6746 0.7300 0.180 Uiso 0.5 1 calc R U P A 1 C24' C 1.2717(19) 0.3488(16) 0.7366(14) 0.103(4) Uani 0.5 1 d D U P A 2 H24D H 1.3656 0.3636 0.7921 0.154 Uiso 0.5 1 calc R U P A 2 H24E H 1.2841 0.3376 0.6561 0.154 Uiso 0.5 1 calc R U P A 2 H24F H 1.2281 0.2699 0.7601 0.154 Uiso 0.5 1 calc R U P A 2 C25' C 1.1416(19) 0.487(2) 0.8598(12) 0.110(4) Uani 0.5 1 d D U P A 2 H25D H 1.0960 0.5719 0.8647 0.166 Uiso 0.5 1 calc R U P A 2 H25E H 1.2328 0.4826 0.9206 0.166 Uiso 0.5 1 calc R U P A 2 H25F H 1.0779 0.4171 0.8728 0.166 Uiso 0.5 1 calc R U P A 2 C26' C 1.2605(15) 0.5977(14) 0.7127(13) 0.106(4) Uani 0.5 1 d D U P A 2 H26D H 1.2004 0.6762 0.7041 0.158 Uiso 0.5 1 calc R U P A 2 H26E H 1.2903 0.5828 0.6392 0.158 Uiso 0.5 1 calc R U P A 2 H26F H 1.3457 0.6096 0.7789 0.158 Uiso 0.5 1 calc R U P A 2 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 C1 0.080(4) 0.138(6) 0.099(4) -0.004(4) 0.036(4) -0.009(4) C2 0.078(4) 0.185(7) 0.155(5) -0.046(5) 0.034(4) -0.023(4) C3 0.072(4) 0.180(6) 0.143(5) -0.060(5) 0.010(4) 0.005(4) C4 0.088(5) 0.174(7) 0.118(5) -0.047(5) 0.013(4) 0.028(4) C5 0.082(4) 0.106(4) 0.091(4) -0.009(4) 0.024(4) 0.022(4) C6 0.062(3) 0.087(4) 0.066(3) -0.022(3) 0.025(3) 0.000(3) C7 0.075(3) 0.097(4) 0.068(3) -0.020(3) 0.027(3) 0.000(3) C8 0.066(3) 0.073(3) 0.058(2) -0.007(2) 0.020(2) -0.009(2) C9 0.057(3) 0.078(3) 0.054(2) -0.010(2) 0.012(2) 0.003(2) C10 0.057(3) 0.077(3) 0.057(3) -0.010(2) 0.010(2) 0.004(2) C11 0.051(3) 0.087(4) 0.051(2) -0.003(2) 0.010(2) 0.004(2) C12 0.096(4) 0.086(4) 0.074(3) -0.001(3) 0.019(3) 0.012(3) C13 0.113(5) 0.104(5) 0.079(4) 0.021(4) 0.022(4) 0.005(4) C14 0.100(5) 0.126(6) 0.075(4) 0.000(4) 0.034(3) -0.015(4) C15 0.100(5) 0.100(5) 0.083(4) -0.006(3) 0.045(3) 0.000(4) C16 0.084(4) 0.083(4) 0.073(3) -0.006(3) 0.033(3) -0.004(3) C17 0.067(3) 0.068(3) 0.049(2) -0.002(2) 0.018(2) -0.004(2) C18 0.079(4) 0.079(4) 0.079(3) 0.023(3) 0.005(3) -0.015(3) C19 0.078(4) 0.078(3) 0.089(4) 0.018(3) 0.006(3) -0.014(3) C20 0.066(3) 0.067(3) 0.056(2) -0.003(2) 0.011(2) 0.002(3) C21 0.094(4) 0.065(3) 0.052(2) 0.005(2) 0.019(3) 0.002(3) C22 0.078(3) 0.073(3) 0.058(3) -0.001(2) 0.024(2) -0.012(3) C23 0.074(4) 0.080(4) 0.071(3) -0.008(3) -0.002(3) 0.005(3) C24 0.087(7) 0.147(10) 0.104(8) -0.017(8) -0.001(6) -0.005(8) C25 0.118(7) 0.145(9) 0.084(6) 0.013(7) -0.011(6) 0.003(8) C26 0.113(8) 0.120(8) 0.105(7) -0.017(7) -0.015(6) 0.000(7) C24' 0.097(7) 0.119(9) 0.077(7) 0.014(6) -0.005(6) 0.008(7) C25' 0.113(7) 0.134(9) 0.075(6) -0.024(7) 0.007(5) 0.005(8) C26' 0.078(7) 0.112(7) 0.110(7) 0.006(6) -0.007(6) -0.023(6) 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' 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 C2 C1 C6 120.5(8) . . ? C2 C1 H1 119.8 . . ? C6 C1 H1 119.8 . . ? C1 C2 C3 119.3(9) . . ? C1 C2 H2 120.3 . . ? C3 C2 H2 120.3 . . ? C4 C3 C2 120.4(8) . . ? C4 C3 H3 119.8 . . ? C2 C3 H3 119.8 . . ? C5 C4 C3 119.5(9) . . ? C5 C4 H4 120.2 . . ? C3 C4 H4 120.2 . . ? C4 C5 C6 122.6(7) . . ? C4 C5 H5 118.7 . . ? C6 C5 H5 118.7 . . ? C5 C6 C1 117.7(6) . . ? C5 C6 C7 122.0(5) . . ? C1 C6 C7 120.2(5) . . ? C6 C7 C8 114.6(4) . . ? C6 C7 H7A 108.6 . . ? C8 C7 H7A 108.6 . . ? C6 C7 H7B 108.6 . . ? C8 C7 H7B 108.6 . . ? H7A C7 H7B 107.6 . . ? C9 C8 C17 112.3(4) . . ? C9 C8 C7 110.7(4) . . ? C17 C8 C7 109.6(4) . . ? C9 C8 H8 108.0 . . ? C17 C8 H8 108.0 . . ? C7 C8 H8 108.0 . . ? C10 C9 C8 178.9(6) . . ? C9 C10 C11 176.8(5) . . ? C16 C11 C12 118.4(5) . . ? C16 C11 C10 120.2(5) . . ? C12 C11 C10 121.3(5) . . ? C13 C12 C11 119.8(6) . . ? C13 C12 H12 120.1 . . ? C11 C12 H12 120.1 . . ? C14 C13 C12 120.8(6) . . ? C14 C13 H13 119.6 . . ? C12 C13 H13 119.6 . . ? C15 C14 C13 119.9(6) . . ? C15 C14 H14 120.1 . . ? C13 C14 H14 120.1 . . ? C14 C15 C16 121.1(6) . . ? C14 C15 H15 119.5 . . ? C16 C15 H15 119.5 . . ? C15 C16 C11 120.0(6) . . ? C15 C16 H16 120.0 . . ? C11 C16 H16 120.0 . . ? C18 C17 C22 116.7(5) . . ? C18 C17 C8 122.0(4) . . ? C22 C17 C8 121.2(4) . . ? C17 C18 C19 121.7(5) . . ? C17 C18 H18 119.1 . . ? C19 C18 H18 119.1 . . ? C20 C19 C18 121.9(5) . . ? C20 C19 H19 119.1 . . ? C18 C19 H19 119.1 . . ? C21 C20 C19 116.5(5) . . ? C21 C20 C23 121.9(4) . . ? C19 C20 C23 121.6(5) . . ? C20 C21 C22 121.5(4) . . ? C20 C21 H21 119.3 . . ? C22 C21 H21 119.3 . . ? C17 C22 C21 121.6(4) . . ? C17 C22 H22 119.2 . . ? C21 C22 H22 119.2 . . ? C24 C23 C26 121.6(12) . . ? C24 C23 C20 111.3(8) . . ? C25' C23 C20 111.6(8) . . ? C26 C23 C20 110.4(7) . . ? C25' C23 C24' 110.7(10) . . ? C20 C23 C24' 109.1(7) . . ? C25' C23 C26' 109.1(10) . . ? C20 C23 C26' 111.5(6) . . ? C24' C23 C26' 104.6(9) . . ? C24 C23 C25 104.6(11) . . ? C26 C23 C25 98.9(11) . . ? C20 C23 C25 108.3(7) . . ? C23 C24 H24A 109.5 . . ? C23 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C23 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? C23 C25 H25A 109.5 . . ? C23 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? C23 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? C23 C26 H26A 109.5 . . ? C23 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? C23 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? C23 C24' H24D 109.5 . . ? C23 C24' H24E 109.5 . . ? H24D C24' H24E 109.5 . . ? C23 C24' H24F 109.5 . . ? H24D C24' H24F 109.5 . . ? H24E C24' H24F 109.5 . . ? C23 C25' H25D 109.5 . . ? C23 C25' H25E 109.5 . . ? H25D C25' H25E 109.5 . . ? C23 C25' H25F 109.5 . . ? H25D C25' H25F 109.5 . . ? H25E C25' H25F 109.5 . . ? C23 C26' H26D 109.5 . . ? C23 C26' H26E 109.5 . . ? H26D C26' H26E 109.5 . . ? C23 C26' H26F 109.5 . . ? H26D C26' H26F 109.5 . . ? H26E C26' H26F 109.5 . . ? 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 C1 C2 1.373(9) . ? C1 C6 1.395(8) . ? C1 H1 0.9300 . ? C2 C3 1.384(12) . ? C2 H2 0.9300 . ? C3 C4 1.360(13) . ? C3 H3 0.9300 . ? C4 C5 1.351(9) . ? C4 H4 0.9300 . ? C5 C6 1.365(8) . ? C5 H5 0.9300 . ? C6 C7 1.495(7) . ? C7 C8 1.549(7) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 C9 1.461(6) . ? C8 C17 1.524(7) . ? C8 H8 0.9800 . ? C9 C10 1.179(6) . ? C10 C11 1.441(6) . ? C11 C16 1.376(7) . ? C11 C12 1.379(8) . ? C12 C13 1.373(8) . ? C12 H12 0.9300 . ? C13 C14 1.353(9) . ? C13 H13 0.9300 . ? C14 C15 1.333(9) . ? C14 H14 0.9300 . ? C15 C16 1.375(7) . ? C15 H15 0.9300 . ? C16 H16 0.9300 . ? C17 C18 1.367(7) . ? C17 C22 1.374(6) . ? C18 C19 1.379(7) . ? C18 H18 0.9300 . ? C19 C20 1.377(7) . ? C19 H19 0.9300 . ? C20 C21 1.371(7) . ? C20 C23 1.529(7) . ? C21 C22 1.390(7) . ? C21 H21 0.9300 . ? C22 H22 0.9300 . ? C23 C24 1.452(17) . ? C23 C25' 1.466(13) . ? C23 C26 1.503(14) . ? C23 C24' 1.576(15) . ? C23 C26' 1.598(13) . ? C23 C25 1.608(15) . ? C24 H24A 0.9600 . ? C24 H24B 0.9600 . ? C24 H24C 0.9600 . ? C25 H25A 0.9600 . ? C25 H25B 0.9600 . ? C25 H25C 0.9600 . ? C26 H26A 0.9600 . ? C26 H26B 0.9600 . ? C26 H26C 0.9600 . ? C24' H24D 0.9600 . ? C24' H24E 0.9600 . ? C24' H24F 0.9600 . ? C25' H25D 0.9600 . ? C25' H25E 0.9600 . ? C25' H25F 0.9600 . ? C26' H26D 0.9600 . ? C26' H26E 0.9600 . ? C26' H26F 0.9600 . ? 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 C6 C1 C2 C3 2.2(11) . . . . ? C1 C2 C3 C4 -1.2(12) . . . . ? C2 C3 C4 C5 0.5(12) . . . . ? C3 C4 C5 C6 -0.9(10) . . . . ? C4 C5 C6 C1 1.9(8) . . . . ? C4 C5 C6 C7 -179.9(6) . . . . ? C2 C1 C6 C5 -2.5(9) . . . . ? C2 C1 C6 C7 179.3(6) . . . . ? C5 C6 C7 C8 -91.4(6) . . . . ? C1 C6 C7 C8 86.8(6) . . . . ? C6 C7 C8 C9 63.3(6) . . . . ? C6 C7 C8 C17 -172.3(5) . . . . ? C16 C11 C12 C13 -2.9(9) . . . . ? C10 C11 C12 C13 175.0(5) . . . . ? C11 C12 C13 C14 1.2(10) . . . . ? C12 C13 C14 C15 0.5(11) . . . . ? C13 C14 C15 C16 -0.4(10) . . . . ? C14 C15 C16 C11 -1.3(9) . . . . ? C12 C11 C16 C15 2.9(8) . . . . ? C10 C11 C16 C15 -174.9(5) . . . . ? C9 C8 C17 C18 46.2(7) . . . . ? C7 C8 C17 C18 -77.3(6) . . . . ? C9 C8 C17 C22 -136.3(5) . . . . ? C7 C8 C17 C22 100.3(5) . . . . ? C22 C17 C18 C19 -2.5(8) . . . . ? C8 C17 C18 C19 175.2(5) . . . . ? C17 C18 C19 C20 1.8(9) . . . . ? C18 C19 C20 C21 0.3(8) . . . . ? C18 C19 C20 C23 -179.3(5) . . . . ? C19 C20 C21 C22 -1.4(7) . . . . ? C23 C20 C21 C22 178.2(5) . . . . ? C18 C17 C22 C21 1.4(7) . . . . ? C8 C17 C22 C21 -176.3(4) . . . . ? C20 C21 C22 C17 0.5(7) . . . . ? C21 C20 C23 C24 91.1(10) . . . . ? C19 C20 C23 C24 -89.4(10) . . . . ? C21 C20 C23 C25' -63.7(10) . . . . ? C19 C20 C23 C25' 115.9(10) . . . . ? C21 C20 C23 C26 -130.7(9) . . . . ? C19 C20 C23 C26 48.9(11) . . . . ? C21 C20 C23 C24' 59.0(9) . . . . ? C19 C20 C23 C24' -121.4(8) . . . . ? C21 C20 C23 C26' 174.1(8) . . . . ? C19 C20 C23 C26' -6.4(9) . . . . ? C21 C20 C23 C25 -23.4(10) . . . . ? C19 C20 C23 C25 156.2(9) . . . . ?