#------------------------------------------------------------------------------ #$Date: 2019-05-18 04:25:56 +0300 (Sat, 18 May 2019) $ #$Revision: 215290 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/55/10/1551070.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_1551070 loop_ _publ_author_name 'Alexy, Eric J.' 'Fulton, Tyler J.' 'Zhang, Haiming' 'Stoltz, Brian M.' _publ_section_title ; Palladium-catalyzed enantioselective decarboxylative allylic alkylation of fully substituted N-acyl indole-derived enol carbonates ; _journal_name_full 'Chemical Science' _journal_paper_doi 10.1039/C9SC01726G _journal_year 2019 _chemical_absolute_configuration ad _chemical_formula_sum 'C26 H23 N O' _chemical_formula_weight 365.45 _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' _symmetry_space_group_name_Hall 'P 2yb' _symmetry_space_group_name_H-M 'P 1 21 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-2017/1 _audit_update_record ; 2019-04-08 deposited with the CCDC. 2019-04-26 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 99.6595(18) _cell_angle_gamma 90 _cell_formula_units_Z 2 _cell_length_a 11.2225(10) _cell_length_b 6.4382(6) _cell_length_c 14.0893(13) _cell_measurement_reflns_used 9956 _cell_measurement_temperature 100(2) _cell_measurement_theta_max 79.79 _cell_measurement_theta_min 3.18 _cell_volume 1003.56(16) _computing_cell_refinement 'SAINT v8.38A (Bruker-AXS, 2013)' _computing_data_collection 'APEX3 v2017.3-0 (Bruker-AXS, 2017)' _computing_data_reduction 'SAINT v8.38A (Bruker-AXS, 2013)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _computing_structure_refinement 'SHELXL-2017/1 (Sheldrick, 2017)' _computing_structure_solution 'SHELXS-2013/1 (Sheldrick, 2013)' _diffrn_ambient_temperature 100(2) _diffrn_detector_area_resol_mean 7.69 _diffrn_measured_fraction_theta_full 0.990 _diffrn_measured_fraction_theta_max 0.972 _diffrn_measurement_device_type 'Bruker D8 VENTURE Kappa Duo PHOTON II CPAD' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54178 _diffrn_reflns_av_R_equivalents 0.0282 _diffrn_reflns_av_unetI/netI 0.0182 _diffrn_reflns_Laue_measured_fraction_full 0.990 _diffrn_reflns_Laue_measured_fraction_max 0.972 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_number 34321 _diffrn_reflns_point_group_measured_fraction_full 0.976 _diffrn_reflns_point_group_measured_fraction_max 0.943 _diffrn_reflns_theta_full 67.679 _diffrn_reflns_theta_max 80.104 _diffrn_reflns_theta_min 3.182 _diffrn_source 'I\mS HB micro-focus sealed tube' _exptl_absorpt_coefficient_mu 0.564 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_correction_T_min 0.8766 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS-2016/2 (Sheldrick, 2014)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.209 _exptl_crystal_density_method 'not measured' _exptl_crystal_description Block _exptl_crystal_F_000 388 _exptl_crystal_size_max 0.500 _exptl_crystal_size_mid 0.500 _exptl_crystal_size_min 0.300 _refine_diff_density_max 0.201 _refine_diff_density_min -0.133 _refine_diff_density_rms 0.027 _refine_ls_abs_structure_details ; Flack x determined using 1799 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). ; _refine_ls_abs_structure_Flack 0.05(4) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.038 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 253 _refine_ls_number_reflns 4134 _refine_ls_number_restraints 1 _refine_ls_restrained_S_all 1.038 _refine_ls_R_factor_all 0.0265 _refine_ls_R_factor_gt 0.0265 _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^)+(0.0359P)^2^+0.1777P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0681 _refine_ls_wR_factor_ref 0.0682 _reflns_Friedel_coverage 0.777 _reflns_Friedel_fraction_full 0.960 _reflns_Friedel_fraction_max 0.907 _reflns_number_gt 4116 _reflns_number_total 4134 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file c9sc01726g3.cif _cod_data_source_block v18448 _cod_database_code 1551070 _shelx_shelxl_version_number 2017/1 _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 0.766 _shelx_estimated_absorpt_t_max 0.849 _shelx_res_file ; TITL V18448 in P2(1) v18448.res created by SHELXL-2017/1 at 07:38:30 on 12-Sep-2018 CELL 1.54178 11.22250 6.43820 14.08930 90.0000 99.6595 90.0000 ZERR 2.00 0.00100 0.00060 0.00130 0.0000 0.0018 0.0000 LATT -1 SYMM -X, 0.5+Y, -Z SFAC C H N O UNIT 52 46 2 2 TEMP -173 SIZE 0.30 0.50 0.50 ACTA WPDB -2 CONF L.S. 10 BOND $H FMAP 2 PLAN 20 HTAB HTAB C37 O1 WGHT 0.035900 0.177700 FVAR 0.64825 O1 4 0.578557 0.181336 0.727260 11.00000 0.02294 0.01482 = 0.03897 -0.00326 -0.00095 0.00216 C1 1 0.578282 0.363795 0.747603 11.00000 0.01783 0.01575 = 0.01838 0.00109 0.00345 -0.00091 C2 1 0.468836 0.506586 0.714104 11.00000 0.01583 0.01393 = 0.01635 0.00034 0.00237 0.00072 C11 1 0.420002 0.596586 0.800622 11.00000 0.01444 0.02013 = 0.01628 -0.00252 0.00219 -0.00299 C12 1 0.414955 0.471089 0.880567 11.00000 0.02101 0.03114 = 0.02086 0.00396 0.00262 -0.00193 AFIX 43 H12 2 0.445787 0.333478 0.882218 11.00000 -1.20000 AFIX 0 C13 1 0.365154 0.545794 0.957868 11.00000 0.02712 0.05861 = 0.01904 0.00112 0.00563 -0.00894 AFIX 43 H13 2 0.362699 0.459358 1.012153 11.00000 -1.20000 AFIX 0 C14 1 0.319275 0.744946 0.956084 11.00000 0.02651 0.06053 = 0.02720 -0.01898 0.01274 -0.00931 AFIX 43 H14 2 0.284589 0.795276 1.008681 11.00000 -1.20000 AFIX 0 C15 1 0.324083 0.870080 0.877689 11.00000 0.02824 0.03391 = 0.04327 -0.01735 0.01471 -0.00214 AFIX 43 H15 2 0.292936 1.007432 0.876516 11.00000 -1.20000 AFIX 0 C16 1 0.374185 0.797320 0.800012 11.00000 0.02359 0.02289 = 0.02793 -0.00367 0.00767 0.00026 AFIX 43 H16 2 0.377069 0.885321 0.746322 11.00000 -1.20000 AFIX 0 C3 1 0.368285 0.366972 0.655921 11.00000 0.01774 0.01673 = 0.01978 -0.00114 0.00093 -0.00118 AFIX 23 H3A 2 0.399872 0.305272 0.600753 11.00000 -1.20000 H3B 2 0.350281 0.251637 0.697786 11.00000 -1.20000 AFIX 0 C21 1 0.252018 0.480295 0.618330 11.00000 0.01629 0.01500 = 0.02208 -0.00202 0.00066 -0.00236 C22 1 0.160151 0.490742 0.673691 11.00000 0.01984 0.02797 = 0.02416 -0.00212 0.00230 -0.00502 AFIX 43 H22 2 0.171027 0.425692 0.735061 11.00000 -1.20000 AFIX 0 C23 1 0.053028 0.594974 0.640266 11.00000 0.01824 0.03167 = 0.03717 -0.00723 0.00711 -0.00197 AFIX 43 H23 2 -0.008287 0.602070 0.679165 11.00000 -1.20000 AFIX 0 C24 1 0.035048 0.688836 0.550348 11.00000 0.01685 0.02456 = 0.04607 -0.00077 -0.00248 0.00199 AFIX 43 H24 2 -0.038356 0.759879 0.527488 11.00000 -1.20000 AFIX 0 C25 1 0.125189 0.678057 0.494096 11.00000 0.02311 0.02310 = 0.03205 0.00612 -0.00303 -0.00166 AFIX 43 H25 2 0.113385 0.741564 0.432366 11.00000 -1.20000 AFIX 0 C26 1 0.232717 0.574630 0.527776 11.00000 0.01854 0.02147 = 0.02350 0.00001 0.00118 -0.00300 AFIX 43 H26 2 0.293855 0.568031 0.488698 11.00000 -1.20000 AFIX 0 C4 1 0.508951 0.676128 0.647411 11.00000 0.01775 0.01545 = 0.01743 0.00170 0.00313 -0.00014 AFIX 23 H4A 2 0.436460 0.749319 0.613668 11.00000 -1.20000 H4B 2 0.560178 0.779274 0.687389 11.00000 -1.20000 AFIX 0 C5 1 0.578123 0.588169 0.574004 11.00000 0.02762 0.02211 = 0.01868 0.00079 0.00726 0.00038 AFIX 43 H5 2 0.535055 0.508510 0.522666 11.00000 -1.20000 AFIX 0 C6 1 0.695268 0.615342 0.576842 11.00000 0.02972 0.03298 = 0.02780 0.00801 0.01257 0.00678 AFIX 93 H6A 2 0.740684 0.694291 0.627331 11.00000 -1.20000 H6B 2 0.734148 0.555946 0.528394 11.00000 -1.20000 AFIX 0 N1 3 0.682606 0.454834 0.799784 11.00000 0.01593 0.01543 = 0.01882 0.00099 0.00227 0.00115 C31 1 0.693549 0.651009 0.843826 11.00000 0.01998 0.01815 = 0.02008 -0.00178 0.00133 -0.00013 AFIX 43 H31 2 0.629286 0.747358 0.843088 11.00000 -1.20000 AFIX 0 C32 1 0.808741 0.682864 0.887409 11.00000 0.02162 0.02415 = 0.02118 -0.00088 0.00019 -0.00264 AFIX 43 H32 2 0.838854 0.803216 0.922462 11.00000 -1.20000 AFIX 0 C33 1 0.877363 0.502403 0.871249 11.00000 0.01897 0.02709 = 0.01740 0.00414 0.00318 -0.00154 C34 1 0.999558 0.450667 0.898361 11.00000 0.01702 0.03962 = 0.02445 0.00646 0.00142 -0.00026 AFIX 43 H34 2 1.054086 0.543561 0.935835 11.00000 -1.20000 AFIX 0 C35 1 1.038879 0.261608 0.869361 11.00000 0.01692 0.04366 = 0.03112 0.01043 0.00491 0.00743 AFIX 43 H35 2 1.121273 0.223517 0.887957 11.00000 -1.20000 AFIX 0 C36 1 0.959851 0.125392 0.813235 11.00000 0.02640 0.03270 = 0.03400 0.00701 0.01007 0.01134 AFIX 43 H36 2 0.990084 -0.002376 0.793316 11.00000 -1.20000 AFIX 0 C37 1 0.837914 0.171858 0.785689 11.00000 0.02289 0.02441 = 0.02706 0.00321 0.00633 0.00417 AFIX 43 H37 2 0.784230 0.078601 0.747637 11.00000 -1.20000 AFIX 0 C38 1 0.798166 0.360869 0.816349 11.00000 0.01534 0.02250 = 0.01711 0.00624 0.00387 0.00134 HKLF 4 REM V18448 in P2(1) REM R1 = 0.0265 for 4116 Fo > 4sig(Fo) and 0.0265 for all 4134 data REM 253 parameters refined using 1 restraints END WGHT 0.0359 0.1776 REM Instructions for potential hydrogen bonds HTAB C37 O1 REM Highest difference peak 0.201, deepest hole -0.133, 1-sigma level 0.027 Q1 1 0.4440 0.5550 0.7598 11.00000 0.05 0.20 Q2 1 0.3149 0.4412 0.6377 11.00000 0.05 0.18 Q3 1 0.5226 0.4387 0.7282 11.00000 0.05 0.17 Q4 1 0.4234 0.4468 0.6814 11.00000 0.05 0.17 Q5 1 0.4953 0.5832 0.6822 11.00000 0.05 0.16 Q6 1 0.7402 0.3975 0.8060 11.00000 0.05 0.15 Q7 1 0.8412 0.5776 0.8972 11.00000 0.05 0.15 Q8 1 0.8470 0.4304 0.8426 11.00000 0.05 0.15 Q9 1 0.2213 0.5520 0.6578 11.00000 0.05 0.14 Q10 1 0.8544 0.4516 0.8226 11.00000 0.05 0.14 Q11 1 0.1048 0.7245 0.5376 11.00000 0.05 0.13 Q12 1 0.5504 0.6332 0.6161 11.00000 0.05 0.13 Q13 1 0.9377 0.4921 0.8673 11.00000 0.05 0.13 Q14 1 0.4118 0.5404 0.8403 11.00000 0.05 0.12 Q15 1 0.6418 0.5408 0.6010 11.00000 0.05 0.12 Q16 1 0.2017 0.4447 0.6347 11.00000 0.05 0.12 Q17 1 0.1823 0.6367 0.5205 11.00000 0.05 0.12 Q18 1 0.7596 0.7038 0.8414 11.00000 0.05 0.11 Q19 1 0.2237 0.4659 0.5651 11.00000 0.05 0.11 Q20 1 0.4266 0.7115 0.8125 11.00000 0.05 0.11 ; _shelx_res_checksum 58596 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 O1 O 0.57856(9) 0.18134(17) 0.72726(8) 0.0263(2) Uani 1 1 d . . C1 C 0.57828(12) 0.3638(2) 0.74760(9) 0.0173(3) Uani 1 1 d . . C2 C 0.46884(11) 0.5066(2) 0.71410(9) 0.0154(3) Uani 1 1 d . . C11 C 0.42000(11) 0.5966(2) 0.80062(9) 0.0170(3) Uani 1 1 d . . C12 C 0.41495(13) 0.4711(3) 0.88057(10) 0.0244(3) Uani 1 1 d . . H12 H 0.445787 0.333478 0.882218 0.029 Uiso 1 1 calc R U C13 C 0.36515(15) 0.5458(3) 0.95787(11) 0.0347(4) Uani 1 1 d . . H13 H 0.362699 0.459358 1.012153 0.042 Uiso 1 1 calc R U C14 C 0.31927(15) 0.7449(3) 0.95608(12) 0.0371(4) Uani 1 1 d . . H14 H 0.284589 0.795276 1.008681 0.045 Uiso 1 1 calc R U C15 C 0.32408(15) 0.8701(3) 0.87769(13) 0.0341(4) Uani 1 1 d . . H15 H 0.292936 1.007432 0.876516 0.041 Uiso 1 1 calc R U C16 C 0.37418(13) 0.7973(2) 0.80001(11) 0.0244(3) Uani 1 1 d . . H16 H 0.377069 0.885321 0.746322 0.029 Uiso 1 1 calc R U C3 C 0.36828(12) 0.3670(2) 0.65592(10) 0.0183(3) Uani 1 1 d . . H3A H 0.399872 0.305272 0.600753 0.022 Uiso 1 1 calc R U H3B H 0.350281 0.251637 0.697786 0.022 Uiso 1 1 calc R U C21 C 0.25202(12) 0.4803(2) 0.61833(9) 0.0181(3) Uani 1 1 d . . C22 C 0.16015(13) 0.4907(3) 0.67369(10) 0.0242(3) Uani 1 1 d . . H22 H 0.171027 0.425692 0.735061 0.029 Uiso 1 1 calc R U C23 C 0.05303(13) 0.5950(3) 0.64027(12) 0.0287(3) Uani 1 1 d . . H23 H -0.008287 0.602070 0.679165 0.034 Uiso 1 1 calc R U C24 C 0.03505(13) 0.6888(3) 0.55035(12) 0.0301(3) Uani 1 1 d . . H24 H -0.038356 0.759879 0.527488 0.036 Uiso 1 1 calc R U C25 C 0.12519(13) 0.6781(3) 0.49410(11) 0.0270(3) Uani 1 1 d . . H25 H 0.113385 0.741564 0.432366 0.032 Uiso 1 1 calc R U C26 C 0.23272(12) 0.5746(2) 0.52778(10) 0.0214(3) Uani 1 1 d . . H26 H 0.293855 0.568031 0.488698 0.026 Uiso 1 1 calc R U C4 C 0.50895(11) 0.6761(2) 0.64741(9) 0.0169(3) Uani 1 1 d . . H4A H 0.436460 0.749319 0.613668 0.020 Uiso 1 1 calc R U H4B H 0.560178 0.779274 0.687389 0.020 Uiso 1 1 calc R U C5 C 0.57812(13) 0.5882(2) 0.57400(10) 0.0224(3) Uani 1 1 d . . H5 H 0.535055 0.508510 0.522666 0.027 Uiso 1 1 calc R U C6 C 0.69527(15) 0.6153(3) 0.57684(11) 0.0293(3) Uani 1 1 d . . H6A H 0.740684 0.694291 0.627331 0.035 Uiso 1 1 calc R U H6B H 0.734148 0.555946 0.528394 0.035 Uiso 1 1 calc R U N1 N 0.68261(10) 0.45483(18) 0.79978(8) 0.0168(2) Uani 1 1 d . . C31 C 0.69355(12) 0.6510(2) 0.84383(9) 0.0196(3) Uani 1 1 d . . H31 H 0.629286 0.747358 0.843088 0.024 Uiso 1 1 calc R U C32 C 0.80874(13) 0.6829(3) 0.88741(10) 0.0227(3) Uani 1 1 d . . H32 H 0.838854 0.803216 0.922462 0.027 Uiso 1 1 calc R U C33 C 0.87736(12) 0.5024(2) 0.87125(9) 0.0211(3) Uani 1 1 d . . C34 C 0.99956(13) 0.4507(3) 0.89836(10) 0.0273(3) Uani 1 1 d . . H34 H 1.054086 0.543561 0.935835 0.033 Uiso 1 1 calc R U C35 C 1.03888(13) 0.2616(3) 0.86936(11) 0.0305(4) Uani 1 1 d . . H35 H 1.121273 0.223517 0.887957 0.037 Uiso 1 1 calc R U C36 C 0.95985(14) 0.1254(3) 0.81324(12) 0.0305(4) Uani 1 1 d . . H36 H 0.990084 -0.002376 0.793316 0.037 Uiso 1 1 calc R U C37 C 0.83791(13) 0.1719(3) 0.78569(10) 0.0245(3) Uani 1 1 d . . H37 H 0.784230 0.078601 0.747637 0.029 Uiso 1 1 calc R U C38 C 0.79817(12) 0.3609(2) 0.81635(9) 0.0182(3) 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 0.0229(5) 0.0148(6) 0.0390(6) -0.0033(4) -0.0009(4) 0.0022(4) C1 0.0178(6) 0.0158(7) 0.0184(6) 0.0011(5) 0.0034(5) -0.0009(5) C2 0.0158(6) 0.0139(7) 0.0164(6) 0.0003(5) 0.0024(5) 0.0007(5) C11 0.0144(6) 0.0201(7) 0.0163(6) -0.0025(5) 0.0022(4) -0.0030(5) C12 0.0210(7) 0.0311(8) 0.0209(6) 0.0040(6) 0.0026(5) -0.0019(6) C13 0.0271(8) 0.0586(12) 0.0190(7) 0.0011(7) 0.0056(6) -0.0089(8) C14 0.0265(8) 0.0605(12) 0.0272(8) -0.0190(8) 0.0127(6) -0.0093(8) C15 0.0282(8) 0.0339(9) 0.0433(9) -0.0174(7) 0.0147(7) -0.0021(7) C16 0.0236(7) 0.0229(8) 0.0279(7) -0.0037(6) 0.0077(6) 0.0003(6) C3 0.0177(6) 0.0167(7) 0.0198(6) -0.0011(5) 0.0009(5) -0.0012(5) C21 0.0163(6) 0.0150(7) 0.0221(6) -0.0020(5) 0.0007(5) -0.0024(5) C22 0.0198(6) 0.0280(8) 0.0242(7) -0.0021(6) 0.0023(5) -0.0050(6) C23 0.0182(7) 0.0317(9) 0.0372(8) -0.0072(7) 0.0071(6) -0.0020(6) C24 0.0169(7) 0.0246(8) 0.0461(9) -0.0008(7) -0.0025(6) 0.0020(6) C25 0.0231(7) 0.0231(8) 0.0320(7) 0.0061(6) -0.0030(6) -0.0017(6) C26 0.0185(6) 0.0215(7) 0.0235(7) 0.0000(5) 0.0012(5) -0.0030(6) C4 0.0178(6) 0.0155(6) 0.0174(6) 0.0017(5) 0.0031(4) -0.0001(5) C5 0.0276(7) 0.0221(8) 0.0187(6) 0.0008(5) 0.0073(5) 0.0004(6) C6 0.0297(8) 0.0330(9) 0.0278(7) 0.0080(6) 0.0126(6) 0.0068(6) N1 0.0159(5) 0.0154(6) 0.0188(5) 0.0010(4) 0.0023(4) 0.0011(4) C31 0.0200(6) 0.0181(7) 0.0201(6) -0.0018(5) 0.0013(5) -0.0001(5) C32 0.0216(7) 0.0241(8) 0.0212(6) -0.0009(6) 0.0002(5) -0.0026(6) C33 0.0190(6) 0.0271(8) 0.0174(6) 0.0041(6) 0.0032(5) -0.0015(5) C34 0.0170(7) 0.0396(9) 0.0244(7) 0.0065(6) 0.0014(5) -0.0003(6) C35 0.0169(7) 0.0437(10) 0.0311(8) 0.0104(7) 0.0049(6) 0.0074(7) C36 0.0264(8) 0.0327(9) 0.0340(8) 0.0070(7) 0.0101(6) 0.0113(6) C37 0.0229(7) 0.0244(8) 0.0271(7) 0.0032(6) 0.0063(5) 0.0042(6) C38 0.0153(6) 0.0225(7) 0.0171(6) 0.0062(5) 0.0039(5) 0.0013(5) 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 O1 C1 N1 119.69(12) O1 C1 C2 122.66(12) N1 C1 C2 117.58(12) C11 C2 C1 110.77(10) C11 C2 C4 113.19(11) C1 C2 C4 107.86(10) C11 C2 C3 108.16(10) C1 C2 C3 106.58(11) C4 C2 C3 110.09(10) C16 C11 C12 118.57(13) C16 C11 C2 121.87(12) C12 C11 C2 119.46(13) C13 C12 C11 120.54(16) C13 C12 H12 119.7 C11 C12 H12 119.7 C14 C13 C12 120.31(16) C14 C13 H13 119.8 C12 C13 H13 119.8 C15 C14 C13 119.60(15) C15 C14 H14 120.2 C13 C14 H14 120.2 C14 C15 C16 120.62(17) C14 C15 H15 119.7 C16 C15 H15 119.7 C11 C16 C15 120.36(15) C11 C16 H16 119.8 C15 C16 H16 119.8 C21 C3 C2 114.28(11) C21 C3 H3A 108.7 C2 C3 H3A 108.7 C21 C3 H3B 108.7 C2 C3 H3B 108.7 H3A C3 H3B 107.6 C22 C21 C26 118.29(13) C22 C21 C3 120.20(12) C26 C21 C3 121.50(12) C23 C22 C21 120.85(14) C23 C22 H22 119.6 C21 C22 H22 119.6 C24 C23 C22 120.35(14) C24 C23 H23 119.8 C22 C23 H23 119.8 C23 C24 C25 119.44(14) C23 C24 H24 120.3 C25 C24 H24 120.3 C24 C25 C26 120.22(14) C24 C25 H25 119.9 C26 C25 H25 119.9 C25 C26 C21 120.85(13) C25 C26 H26 119.6 C21 C26 H26 119.6 C5 C4 C2 112.72(12) C5 C4 H4A 109.0 C2 C4 H4A 109.0 C5 C4 H4B 109.0 C2 C4 H4B 109.0 H4A C4 H4B 107.8 C6 C5 C4 123.74(14) C6 C5 H5 118.1 C4 C5 H5 118.1 C5 C6 H6A 120.0 C5 C6 H6B 120.0 H6A C6 H6B 120.0 C1 N1 C31 127.69(12) C1 N1 C38 124.72(12) C31 N1 C38 107.59(11) C32 C31 N1 110.11(13) C32 C31 H31 124.9 N1 C31 H31 124.9 C31 C32 C33 107.67(13) C31 C32 H32 126.2 C33 C32 H32 126.2 C34 C33 C38 119.61(15) C34 C33 C32 132.62(15) C38 C33 C32 107.76(12) C35 C34 C33 118.44(15) C35 C34 H34 120.8 C33 C34 H34 120.8 C34 C35 C36 121.20(14) C34 C35 H35 119.4 C36 C35 H35 119.4 C37 C36 C35 121.68(16) C37 C36 H36 119.2 C35 C36 H36 119.2 C38 C37 C36 116.98(15) C38 C37 H37 121.5 C36 C37 H37 121.5 C37 C38 C33 122.06(13) C37 C38 N1 131.03(13) C33 C38 N1 106.87(12) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance O1 C1 1.2093(19) C1 N1 1.4021(17) C1 C2 1.5434(18) C2 C11 1.5317(17) C2 C4 1.5553(17) C2 C3 1.5630(18) C11 C16 1.390(2) C11 C12 1.3950(19) C12 C13 1.391(2) C12 H12 0.9500 C13 C14 1.380(3) C13 H13 0.9500 C14 C15 1.375(3) C14 H14 0.9500 C15 C16 1.393(2) C15 H15 0.9500 C16 H16 0.9500 C3 C21 1.5111(18) C3 H3A 0.9900 C3 H3B 0.9900 C21 C22 1.3949(19) C21 C26 1.3967(19) C22 C23 1.388(2) C22 H22 0.9500 C23 C24 1.387(2) C23 H23 0.9500 C24 C25 1.388(2) C24 H24 0.9500 C25 C26 1.390(2) C25 H25 0.9500 C26 H26 0.9500 C4 C5 1.5041(18) C4 H4A 0.9900 C4 H4B 0.9900 C5 C6 1.320(2) C5 H5 0.9500 C6 H6A 0.9500 C6 H6B 0.9500 N1 C31 1.4035(18) N1 C38 1.4145(17) C31 C32 1.3505(19) C31 H31 0.9500 C32 C33 1.433(2) C32 H32 0.9500 C33 C34 1.4006(19) C33 C38 1.410(2) C34 C35 1.380(3) C34 H34 0.9500 C35 C36 1.395(3) C35 H35 0.9500 C36 C37 1.391(2) C36 H36 0.9500 C37 C38 1.390(2) C37 H37 0.9500 loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_publ_flag C37 H37 O1 0.95 2.37 2.8895(18) 113.8 yes 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 O1 C1 C2 C11 118.88(14) N1 C1 C2 C11 -64.19(15) O1 C1 C2 C4 -116.74(14) N1 C1 C2 C4 60.19(14) O1 C1 C2 C3 1.45(17) N1 C1 C2 C3 178.38(10) C1 C2 C11 C16 144.05(13) C4 C2 C11 C16 22.77(17) C3 C2 C11 C16 -99.49(14) C1 C2 C11 C12 -39.49(16) C4 C2 C11 C12 -160.77(12) C3 C2 C11 C12 76.97(14) C16 C11 C12 C13 0.0(2) C2 C11 C12 C13 -176.61(13) C11 C12 C13 C14 0.5(2) C12 C13 C14 C15 -0.6(2) C13 C14 C15 C16 0.3(2) C12 C11 C16 C15 -0.2(2) C2 C11 C16 C15 176.26(14) C14 C15 C16 C11 0.1(2) C11 C2 C3 C21 59.85(14) C1 C2 C3 C21 178.99(11) C4 C2 C3 C21 -64.29(14) C2 C3 C21 C22 -90.62(15) C2 C3 C21 C26 90.14(15) C26 C21 C22 C23 -1.0(2) C3 C21 C22 C23 179.75(14) C21 C22 C23 C24 0.7(2) C22 C23 C24 C25 -0.1(2) C23 C24 C25 C26 -0.2(2) C24 C25 C26 C21 0.0(2) C22 C21 C26 C25 0.6(2) C3 C21 C26 C25 179.89(14) C11 C2 C4 C5 169.03(11) C1 C2 C4 C5 46.13(14) C3 C2 C4 C5 -69.79(14) C2 C4 C5 C6 -108.85(16) O1 C1 N1 C31 -168.09(13) C2 C1 N1 C31 14.88(19) O1 C1 N1 C38 12.5(2) C2 C1 N1 C38 -164.51(11) C1 N1 C31 C32 179.91(13) C38 N1 C31 C32 -0.61(15) N1 C31 C32 C33 0.49(16) C31 C32 C33 C34 179.27(15) C31 C32 C33 C38 -0.18(16) C38 C33 C34 C35 0.6(2) C32 C33 C34 C35 -178.82(15) C33 C34 C35 C36 0.9(2) C34 C35 C36 C37 -1.3(2) C35 C36 C37 C38 0.2(2) C36 C37 C38 C33 1.3(2) C36 C37 C38 N1 178.78(14) C34 C33 C38 C37 -1.7(2) C32 C33 C38 C37 177.85(12) C34 C33 C38 N1 -179.72(12) C32 C33 C38 N1 -0.19(14) C1 N1 C38 C37 2.2(2) C31 N1 C38 C37 -177.32(14) C1 N1 C38 C33 179.98(12) C31 N1 C38 C33 0.48(14)