#------------------------------------------------------------------------------ #$Date: 2020-07-06 06:48:41 +0300 (Mon, 06 Jul 2020) $ #$Revision: 253990 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/15/75/7157503.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_7157503 loop_ _publ_author_name 'Zhao, Jia-Hui' 'Zhou, Zhao-Zhao' 'Zhang, Yue' 'Su, Xuan' 'Chen, Xi-Meng' 'Liang, Yong-Min' _publ_section_title ; Visible-light-mediated borylation of aryl and alkyl halides with a palladium complex. ; _journal_issue 23 _journal_name_full 'Organic & biomolecular chemistry' _journal_page_first 4390 _journal_paper_doi 10.1039/d0ob00028k _journal_volume 18 _journal_year 2020 _chemical_formula_moiety 'C14 H18 B N O2' _chemical_formula_sum 'C14 H18 B N O2' _chemical_formula_weight 243.10 _space_group_crystal_system orthorhombic _space_group_IT_number 61 _space_group_name_Hall '-P 2ac 2ab' _space_group_name_H-M_alt 'P b c a' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _audit_creation_date 2019-10-25 _audit_creation_method ; Olex2 1.2 (compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506) ; _audit_update_record ; 2020-05-04 deposited with the CCDC. 2020-05-13 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_formula_units_Z 8 _cell_length_a 10.3720(3) _cell_length_b 12.8487(4) _cell_length_c 21.0007(8) _cell_measurement_reflns_used 2329 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 69.7650 _cell_measurement_theta_min 8.0750 _cell_volume 2798.69(16) _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) (compiled Feb 1 2013,16:14:44) ; _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) (compiled Feb 1 2013,16:14:44) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) (compiled Feb 1 2013,16:14:44) ; _computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 (Dolomanov et al., 2009)' _computing_structure_refinement 'ShelXL (Sheldrick, 2015)' _computing_structure_solution 'ShelXS (Sheldrick, 2008)' _diffrn_ambient_temperature 293(2) _diffrn_detector_area_resol_mean 16.0733 _diffrn_measured_fraction_theta_full 0.976 _diffrn_measured_fraction_theta_max 0.976 _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega -41.00 10.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - -8.5000 111.0000 120.0000 51 #__ type_ start__ end____ width___ exp.time_ 2 omega -28.00 8.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - -8.5000 111.0000 0.0000 36 #__ type_ start__ end____ width___ exp.time_ 3 omega -58.00 -30.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - -8.5000 111.0000 0.0000 28 #__ type_ start__ end____ width___ exp.time_ 4 omega 40.00 66.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 54.0000 -38.0000 -120.0000 26 #__ type_ start__ end____ width___ exp.time_ 5 omega 21.00 68.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 54.0000 -57.0000 120.0000 47 #__ type_ start__ end____ width___ exp.time_ 6 omega -17.00 9.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 54.0000 -38.0000 -120.0000 26 #__ type_ start__ end____ width___ exp.time_ 7 omega -13.00 17.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 54.0000 -57.0000 120.0000 30 #__ type_ start__ end____ width___ exp.time_ 8 omega 88.00 114.00 1.0000 3.0000 omega____ theta____ kappa____ phi______ frames - 108.0000 -111.0000 0.0000 26 #__ type_ start__ end____ width___ exp.time_ 9 omega 48.00 82.00 1.0000 3.0000 omega____ theta____ kappa____ phi______ frames - 108.0000 -111.0000 0.0000 34 #__ type_ start__ end____ width___ exp.time_ 10 omega 36.00 82.00 1.0000 3.0000 omega____ theta____ kappa____ phi______ frames - 108.0000 -25.0000 -90.0000 46 #__ type_ start__ end____ width___ exp.time_ 11 omega 48.00 104.00 1.0000 3.0000 omega____ theta____ kappa____ phi______ frames - 108.0000 -50.0000 -150.0000 56 #__ type_ start__ end____ width___ exp.time_ 12 omega 100.00 136.00 1.0000 3.0000 omega____ theta____ kappa____ phi______ frames - 108.0000 111.0000 -150.0000 36 #__ type_ start__ end____ width___ exp.time_ 13 omega 102.00 165.00 1.0000 3.0000 omega____ theta____ kappa____ phi______ frames - 108.0000 111.0000 -90.0000 63 #__ type_ start__ end____ width___ exp.time_ 14 omega 48.00 84.00 1.0000 3.0000 omega____ theta____ kappa____ phi______ frames - 108.0000 -38.0000 -180.0000 36 #__ type_ start__ end____ width___ exp.time_ 15 omega 54.00 101.00 1.0000 3.0000 omega____ theta____ kappa____ phi______ frames - 108.0000 -50.0000 0.0000 47 #__ type_ start__ end____ width___ exp.time_ 16 omega 142.00 171.00 1.0000 3.0000 omega____ theta____ kappa____ phi______ frames - 108.0000 63.0000 0.0000 29 ; _diffrn_measurement_device_type 'SuperNova, Dual, Cu at zero, Eos' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 0.0098954000 _diffrn_orient_matrix_UB_12 0.0411805000 _diffrn_orient_matrix_UB_13 -0.0687388000 _diffrn_orient_matrix_UB_21 0.1129913000 _diffrn_orient_matrix_UB_22 0.0708417000 _diffrn_orient_matrix_UB_23 0.0198248000 _diffrn_orient_matrix_UB_31 0.0959472000 _diffrn_orient_matrix_UB_32 -0.0874632000 _diffrn_orient_matrix_UB_33 -0.0162916000 _diffrn_radiation_monochromator mirror _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54184 _diffrn_reflns_av_R_equivalents 0.0264 _diffrn_reflns_av_unetI/netI 0.0301 _diffrn_reflns_Laue_measured_fraction_full 0.976 _diffrn_reflns_Laue_measured_fraction_max 0.976 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_number 6308 _diffrn_reflns_point_group_measured_fraction_full 0.976 _diffrn_reflns_point_group_measured_fraction_max 0.976 _diffrn_reflns_theta_full 66.589 _diffrn_reflns_theta_max 66.589 _diffrn_reflns_theta_min 4.210 _diffrn_source 'SuperNova (Cu) X-ray Source' _exptl_absorpt_coefficient_mu 0.598 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.60606 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) (compiled Feb 1 2013,16:14:44) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour 'clear light colourless' _exptl_crystal_colour_lustre clear _exptl_crystal_colour_modifier light _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.154 _exptl_crystal_description block _exptl_crystal_F_000 1040 _exptl_crystal_size_max 0.21 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.14 _refine_diff_density_max 0.137 _refine_diff_density_min -0.244 _refine_diff_density_rms 0.039 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.055 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 216 _refine_ls_number_reflns 2414 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.055 _refine_ls_R_factor_all 0.0613 _refine_ls_R_factor_gt 0.0518 _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^)+(0.0770P)^2^+0.3437P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1352 _refine_ls_wR_factor_ref 0.1471 _reflns_Friedel_coverage 0.000 _reflns_number_gt 1963 _reflns_number_total 2414 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d0ob00028k2.cif _cod_data_source_block zhaojh_1022 _cod_depositor_comments 'Adding full bibliography for 7157503.cif.' _cod_original_cell_volume 2798.70(15) _cod_database_code 7157503 _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. ; _reflns_odcompleteness_completeness 96.76 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 66.97 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups, All N(H) groups At 1.5 times of: All C(H,H,H) groups 2. Others Fixed Sof: C10(0.6) C11(0.6) H11A(0.6) H11B(0.6) H11C(0.6) C12(0.6) H12A(0.6) H12B(0.6) H12C(0.6) C13(0.6) H13A(0.6) H13B(0.6) H13C(0.6) C14(0.6) H14A(0.6) H14B(0.6) H14C(0.6) C10'(0.4) C11'(0.4) H11D(0.4) H11E(0.4) H11F(0.4) C12'(0.4) H12D(0.4) H12E(0.4) H12F(0.4) C13'(0.4) H13D(0.4) H13E(0.4) H13F(0.4) C14'(0.4) H14D(0.4) H14E(0.4) H14F(0.4) 3.a Aromatic/amide H refined with riding coordinates: N1(H1), C1(H1A), C2(H2), C4(H4), C6(H6), C7(H7) 3.b Idealised Me refined as rotating group: C11(H11A,H11B,H11C), C12(H12A,H12B,H12C), C13(H13A,H13B,H13C), C14(H14A,H14B, H14C), C11'(H11D,H11E,H11F), C12'(H12D,H12E,H12F), C13'(H13D,H13E,H13F), C14'(H14D,H14E,H14F) ; _shelx_res_file ; TITL zhaojh_1022 in Pbca #61 zhaojh_1022.res created by SHELXL-2018/3 at 16:37:54 on 25-Oct-2019 REM reset to Pbca #61 CELL 1.54184 10.372015 12.848719 21.000715 90 90 90 ZERR 8 0.000287 0.00037 0.000776 0 0 0 LATT 1 SYMM 0.5-X,-Y,0.5+Z SYMM 0.5+X,0.5-Y,-Z SYMM -X,0.5+Y,0.5-Z SFAC C H B N O UNIT 112 144 8 8 16 L.S. 10 PLAN 20 BOND $H HTAB CONF fmap 2 acta SHEL 999 0.84 REM REM REM WGHT 0.077000 0.343700 FVAR 7.85190 O1 5 0.065829 0.801436 0.134171 11.00000 0.04813 0.04709 = 0.07262 -0.00343 0.01320 -0.00600 O2 5 0.143746 0.674951 0.069587 11.00000 0.06016 0.05759 = 0.09631 -0.01300 0.02670 -0.00636 N1 4 -0.393581 0.469396 0.181219 11.00000 0.05219 0.05829 = 0.09492 -0.00039 -0.00429 -0.01864 AFIX 43 H1 2 -0.423213 0.408818 0.171779 11.00000 -1.20000 AFIX 0 C1 1 -0.449818 0.538044 0.221972 11.00000 0.05100 0.07667 = 0.08374 -0.00376 0.00881 -0.01505 AFIX 43 H1A 2 -0.526616 0.526558 0.243721 11.00000 -1.20000 AFIX 0 C2 1 -0.377860 0.625212 0.226208 11.00000 0.05129 0.07107 = 0.07516 -0.01069 0.00949 -0.01313 AFIX 43 H2 2 -0.395639 0.683417 0.251024 11.00000 -1.20000 AFIX 0 C3 1 -0.268778 0.611093 0.185195 11.00000 0.04457 0.05234 = 0.05408 -0.00071 -0.00345 -0.00670 C4 1 -0.161439 0.671548 0.169352 11.00000 0.04734 0.04472 = 0.05377 -0.00436 -0.00220 -0.00736 AFIX 43 H4 2 -0.151719 0.737102 0.187503 11.00000 -1.20000 AFIX 0 C5 1 -0.069369 0.635385 0.127070 11.00000 0.04183 0.04681 = 0.05142 0.00195 -0.00523 -0.00130 C6 1 -0.086655 0.535376 0.100370 11.00000 0.04989 0.05019 = 0.06872 -0.00615 -0.00016 0.00330 AFIX 43 H6 2 -0.025434 0.510366 0.071863 11.00000 -1.20000 AFIX 0 C7 1 -0.190919 0.473780 0.115108 11.00000 0.05780 0.04427 = 0.08615 -0.01171 -0.00750 -0.00327 AFIX 43 H7 2 -0.200249 0.408068 0.097123 11.00000 -1.20000 AFIX 0 C8 1 -0.281743 0.512160 0.157459 11.00000 0.04372 0.04842 = 0.06682 0.00127 -0.00788 -0.00600 C9 1 0.184320 0.843347 0.106988 11.00000 0.07079 0.07313 = 0.08268 -0.01196 0.02828 -0.02953 B1 3 0.048628 0.703756 0.109932 11.00000 0.04396 0.04716 = 0.05174 0.00340 0.00050 0.00090 PART 1 C10 1 0.247240 0.754036 0.077178 10.60000 0.05197 0.05211 = 0.07780 0.00097 0.01437 -0.00511 C11 1 0.348258 0.713381 0.124233 10.60000 0.06093 0.07541 = 0.13895 0.00329 -0.00207 0.00733 AFIX 137 H11A 2 0.310449 0.707679 0.165812 10.60000 -1.50000 H11B 2 0.419725 0.760793 0.125767 10.60000 -1.50000 H11C 2 0.377899 0.646196 0.110607 10.60000 -1.50000 AFIX 0 C12 1 0.307171 0.767437 0.013175 10.60000 0.11451 0.10602 = 0.10316 -0.01115 0.05754 -0.01689 AFIX 137 H12A 2 0.346408 0.703177 0.000199 10.60000 -1.50000 H12B 2 0.371630 0.820954 0.015191 10.60000 -1.50000 H12C 2 0.242067 0.786810 -0.017078 10.60000 -1.50000 AFIX 0 C13 1 0.244314 0.915619 0.151704 10.60000 0.05775 0.08935 = 0.11252 -0.02961 0.01434 -0.01908 AFIX 137 H13A 2 0.186509 0.972388 0.159965 10.60000 -1.50000 H13B 2 0.322903 0.941974 0.133728 10.60000 -1.50000 H13C 2 0.262980 0.880019 0.190822 10.60000 -1.50000 AFIX 0 C14 1 0.120278 0.921039 0.051279 10.60000 0.09132 0.07893 = 0.11713 0.04222 0.00563 0.00273 AFIX 137 H14A 2 0.077700 0.879419 0.019672 10.60000 -1.50000 H14B 2 0.187425 0.961062 0.031525 10.60000 -1.50000 H14C 2 0.059009 0.967158 0.070717 10.60000 -1.50000 AFIX 0 PART 0 PART 2 C10' 1 0.217235 0.767564 0.051092 10.40000 0.04250 0.06675 = 0.07722 0.00952 0.01433 0.00103 C11' 1 0.355928 0.729774 0.038360 10.40000 0.05993 0.08941 = 0.14612 0.00690 0.04648 0.00432 AFIX 137 H11D 2 0.388637 0.695412 0.075599 10.40000 -1.50000 H11E 2 0.409716 0.788339 0.028359 10.40000 -1.50000 H11F 2 0.355796 0.682037 0.003194 10.40000 -1.50000 AFIX 0 C12' 1 0.161377 0.817195 -0.007997 10.40000 0.07954 0.12741 = 0.07312 0.03230 0.00498 -0.02269 AFIX 137 H12D 2 0.157116 0.766492 -0.041506 10.40000 -1.50000 H12E 2 0.215244 0.874061 -0.021089 10.40000 -1.50000 H12F 2 0.076274 0.842573 0.001056 10.40000 -1.50000 AFIX 0 C13' 1 0.295498 0.800955 0.166247 10.40000 0.06201 0.14214 = 0.08727 0.01734 -0.01343 -0.04477 AFIX 137 H13D 2 0.274677 0.833118 0.206206 10.40000 -1.50000 H13E 2 0.381373 0.820222 0.153925 10.40000 -1.50000 H13F 2 0.290340 0.726685 0.170538 10.40000 -1.50000 AFIX 0 C14' 1 0.200537 0.947123 0.100656 10.40000 0.08636 0.05579 = 0.12843 -0.00472 0.03218 -0.01809 AFIX 137 H14D 2 0.130184 0.975590 0.076593 10.40000 -1.50000 H14E 2 0.280128 0.960689 0.078848 10.40000 -1.50000 H14F 2 0.202826 0.978859 0.142024 10.40000 -1.50000 AFIX 0 HKLF 4 REM zhaojh_1022 in Pbca #61 REM wR2 = 0.1471, GooF = S = 1.055, Restrained GooF = 1.055 for all data REM R1 = 0.0518 for 1963 Fo > 4sig(Fo) and 0.0613 for all 2414 data REM 216 parameters refined using 0 restraints END WGHT 0.0768 0.3453 REM Instructions for potential hydrogen bonds EQIV $1 -x-1/2, y-1/2, z HTAB N1 O1_$1 REM Highest difference peak 0.137, deepest hole -0.244, 1-sigma level 0.039 Q1 1 -0.0064 0.6583 0.1242 11.00000 0.05 0.14 Q2 1 -0.4351 0.4153 0.1378 11.00000 0.05 0.12 Q3 1 -0.2761 0.5737 0.1581 11.00000 0.05 0.12 Q4 1 0.2395 0.8219 0.1359 11.00000 0.05 0.12 Q5 1 0.2694 0.9971 0.0610 11.00000 0.05 0.11 Q6 1 -0.1893 0.6183 0.1882 11.00000 0.05 0.11 Q7 1 -0.4775 0.7777 0.2696 11.00000 0.05 0.11 Q8 1 0.2335 0.9443 0.0214 11.00000 0.05 0.11 Q9 1 -0.1239 0.7154 0.2175 11.00000 0.05 0.11 Q10 1 0.2311 0.8022 0.0911 11.00000 0.05 0.11 Q11 1 0.1636 0.6587 0.1116 11.00000 0.05 0.10 Q12 1 -0.0228 0.9643 0.1117 11.00000 0.05 0.10 Q13 1 0.1806 0.9026 0.0014 11.00000 0.05 0.10 Q14 1 -0.3407 0.5176 0.0820 11.00000 0.05 0.10 Q15 1 -0.1126 0.6783 0.2529 11.00000 0.05 0.10 Q16 1 -0.0687 0.6554 0.1627 11.00000 0.05 0.10 Q17 1 -0.0702 0.7547 0.1996 11.00000 0.05 0.09 Q18 1 0.0516 0.5519 0.0461 11.00000 0.05 0.09 Q19 1 0.1627 0.8849 0.0105 11.00000 0.05 0.09 Q20 1 -0.1585 0.7789 0.1793 11.00000 0.05 0.09 ; _shelx_res_checksum 22617 _olex2_date_sample_data_collection 2019-10-23 _olex2_submission_special_instructions 'No special instructions were received' loop_ _space_group_symop_operation_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z-1/2' '-x-1/2, y-1/2, z' 'x, -y-1/2, z-1/2' 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 O1 O 0.06583(11) 0.80144(9) 0.13417(6) 0.0559(3) Uani 1 1 d . . . . . O2 O 0.14375(13) 0.67495(10) 0.06959(7) 0.0714(4) Uani 1 1 d . . . . . N1 N -0.39358(15) 0.46940(12) 0.18122(9) 0.0685(5) Uani 1 1 d . . . . . H1 H -0.423213 0.408818 0.171779 0.082 Uiso 1 1 calc R . . . . C1 C -0.44982(18) 0.53804(17) 0.22197(10) 0.0705(5) Uani 1 1 d . . . . . H1A H -0.526616 0.526558 0.243721 0.085 Uiso 1 1 calc R . . . . C2 C -0.37786(18) 0.62521(16) 0.22621(10) 0.0658(5) Uani 1 1 d . . . . . H2 H -0.395639 0.683417 0.251024 0.079 Uiso 1 1 calc R . . . . C3 C -0.26878(15) 0.61109(13) 0.18519(8) 0.0503(4) Uani 1 1 d . . . . . C4 C -0.16144(15) 0.67155(12) 0.16935(7) 0.0486(4) Uani 1 1 d . . . . . H4 H -0.151719 0.737102 0.187503 0.058 Uiso 1 1 calc R . . . . C5 C -0.06937(14) 0.63538(12) 0.12707(7) 0.0467(4) Uani 1 1 d . . . . . C6 C -0.08666(17) 0.53538(13) 0.10037(9) 0.0563(4) Uani 1 1 d . . . . . H6 H -0.025434 0.510366 0.071863 0.068 Uiso 1 1 calc R . . . . C7 C -0.19092(18) 0.47378(13) 0.11511(9) 0.0627(5) Uani 1 1 d . . . . . H7 H -0.200249 0.408068 0.097123 0.075 Uiso 1 1 calc R . . . . C8 C -0.28174(15) 0.51216(13) 0.15746(8) 0.0530(4) Uani 1 1 d . . . . . C9 C 0.1843(2) 0.84335(17) 0.10699(11) 0.0755(6) Uani 1 1 d . . . . . B1 B 0.04863(17) 0.70376(14) 0.10993(9) 0.0476(4) Uani 1 1 d . . . . . C10 C 0.2472(5) 0.7540(4) 0.0772(2) 0.0606(11) Uani 0.6 1 d . . P A 1 C11 C 0.3483(4) 0.7134(3) 0.1242(2) 0.0918(12) Uani 0.6 1 d . . P A 1 H11A H 0.310449 0.707679 0.165812 0.138 Uiso 0.6 1 calc GR . P A 1 H11B H 0.419725 0.760793 0.125767 0.138 Uiso 0.6 1 calc GR . P A 1 H11C H 0.377899 0.646196 0.110607 0.138 Uiso 0.6 1 calc GR . P A 1 C12 C 0.3072(6) 0.7674(5) 0.0132(3) 0.1079(19) Uani 0.6 1 d . . P A 1 H12A H 0.346408 0.703177 0.000199 0.162 Uiso 0.6 1 calc GR . P A 1 H12B H 0.371630 0.820954 0.015191 0.162 Uiso 0.6 1 calc GR . P A 1 H12C H 0.242067 0.786810 -0.017078 0.162 Uiso 0.6 1 calc GR . P A 1 C13 C 0.2443(4) 0.9156(3) 0.1517(2) 0.0865(12) Uani 0.6 1 d . . P A 1 H13A H 0.186509 0.972388 0.159965 0.130 Uiso 0.6 1 calc GR . P A 1 H13B H 0.322903 0.941974 0.133728 0.130 Uiso 0.6 1 calc GR . P A 1 H13C H 0.262980 0.880019 0.190822 0.130 Uiso 0.6 1 calc GR . P A 1 C14 C 0.1203(4) 0.9210(3) 0.0513(2) 0.0958(13) Uani 0.6 1 d . . P A 1 H14A H 0.077700 0.879419 0.019672 0.144 Uiso 0.6 1 calc GR . P A 1 H14B H 0.187425 0.961062 0.031525 0.144 Uiso 0.6 1 calc GR . P A 1 H14C H 0.059009 0.967158 0.070717 0.144 Uiso 0.6 1 calc GR . P A 1 C10' C 0.2172(7) 0.7676(7) 0.0511(3) 0.0622(17) Uani 0.4 1 d . . P A 2 C11' C 0.3559(7) 0.7298(7) 0.0384(5) 0.098(3) Uani 0.4 1 d . . P A 2 H11D H 0.388637 0.695412 0.075599 0.148 Uiso 0.4 1 calc GR . P A 2 H11E H 0.409716 0.788339 0.028359 0.148 Uiso 0.4 1 calc GR . P A 2 H11F H 0.355796 0.682037 0.003194 0.148 Uiso 0.4 1 calc GR . P A 2 C12' C 0.1614(6) 0.8172(6) -0.0080(3) 0.093(2) Uani 0.4 1 d . . P A 2 H12D H 0.157116 0.766492 -0.041506 0.140 Uiso 0.4 1 calc GR . P A 2 H12E H 0.215244 0.874061 -0.021089 0.140 Uiso 0.4 1 calc GR . P A 2 H12F H 0.076274 0.842573 0.001056 0.140 Uiso 0.4 1 calc GR . P A 2 C13' C 0.2955(6) 0.8010(6) 0.1662(3) 0.097(2) Uani 0.4 1 d . . P A 2 H13D H 0.274677 0.833118 0.206206 0.146 Uiso 0.4 1 calc GR . P A 2 H13E H 0.381373 0.820222 0.153925 0.146 Uiso 0.4 1 calc GR . P A 2 H13F H 0.290340 0.726685 0.170538 0.146 Uiso 0.4 1 calc GR . P A 2 C14' C 0.2005(7) 0.9471(4) 0.1007(4) 0.0902(19) Uani 0.4 1 d . . P A 2 H14D H 0.130184 0.975590 0.076593 0.135 Uiso 0.4 1 calc GR . P A 2 H14E H 0.280128 0.960689 0.078848 0.135 Uiso 0.4 1 calc GR . P A 2 H14F H 0.202826 0.978859 0.142024 0.135 Uiso 0.4 1 calc GR . 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 O1 0.0481(6) 0.0471(6) 0.0726(8) -0.0034(5) 0.0132(5) -0.0060(5) O2 0.0602(8) 0.0576(7) 0.0963(10) -0.0130(6) 0.0267(7) -0.0064(6) N1 0.0522(8) 0.0583(9) 0.0949(12) -0.0004(8) -0.0043(8) -0.0186(7) C1 0.0510(10) 0.0767(12) 0.0837(13) -0.0038(10) 0.0088(9) -0.0151(9) C2 0.0513(9) 0.0711(11) 0.0752(11) -0.0107(9) 0.0095(9) -0.0131(8) C3 0.0446(8) 0.0523(8) 0.0541(9) -0.0007(7) -0.0034(7) -0.0067(7) C4 0.0473(8) 0.0447(8) 0.0538(8) -0.0044(6) -0.0022(7) -0.0074(6) C5 0.0418(8) 0.0468(8) 0.0514(8) 0.0019(6) -0.0052(6) -0.0013(6) C6 0.0499(9) 0.0502(9) 0.0687(10) -0.0061(8) -0.0002(8) 0.0033(7) C7 0.0578(10) 0.0443(8) 0.0861(12) -0.0117(8) -0.0075(9) -0.0033(8) C8 0.0437(8) 0.0484(8) 0.0668(9) 0.0013(7) -0.0079(7) -0.0060(7) C9 0.0708(13) 0.0731(12) 0.0827(13) -0.0120(10) 0.0283(11) -0.0295(10) B1 0.0440(9) 0.0472(9) 0.0517(9) 0.0034(7) 0.0005(7) 0.0009(7) C10 0.052(3) 0.052(2) 0.078(3) 0.001(2) 0.014(2) -0.0051(17) C11 0.061(2) 0.075(2) 0.139(4) 0.003(2) -0.002(2) 0.0073(18) C12 0.115(5) 0.106(4) 0.103(4) -0.011(3) 0.058(4) -0.017(3) C13 0.058(2) 0.089(3) 0.113(3) -0.030(2) 0.014(2) -0.0191(19) C14 0.091(3) 0.079(2) 0.117(3) 0.042(2) 0.006(3) 0.003(2) C10' 0.043(3) 0.067(3) 0.077(5) 0.010(4) 0.014(3) 0.001(3) C11' 0.060(4) 0.089(5) 0.146(8) 0.007(5) 0.046(5) 0.004(3) C12' 0.080(4) 0.127(5) 0.073(3) 0.032(3) 0.005(3) -0.023(4) C13' 0.062(3) 0.142(6) 0.087(4) 0.017(4) -0.013(3) -0.045(4) C14' 0.086(4) 0.056(3) 0.128(5) -0.005(3) 0.032(4) -0.018(3) 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' B B 0.0090 0.0039 '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_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag B1 O1 C9 107.67(14) . . ? B1 O2 C10 105.8(2) . . ? B1 O2 C10' 108.9(3) . . ? C1 N1 H1 125.4 . . ? C1 N1 C8 109.29(15) . . ? C8 N1 H1 125.4 . . ? N1 C1 H1A 125.0 . . ? C2 C1 N1 110.04(17) . . ? C2 C1 H1A 125.0 . . ? C1 C2 H2 126.5 . . ? C1 C2 C3 106.98(18) . . ? C3 C2 H2 126.5 . . ? C4 C3 C2 134.54(16) . . ? C4 C3 C8 118.72(15) . . ? C8 C3 C2 106.74(15) . . ? C3 C4 H4 119.5 . . ? C5 C4 C3 121.04(14) . . ? C5 C4 H4 119.5 . . ? C4 C5 C6 118.17(15) . . ? C4 C5 B1 120.25(14) . . ? C6 C5 B1 121.58(15) . . ? C5 C6 H6 118.9 . . ? C7 C6 C5 122.25(16) . . ? C7 C6 H6 118.9 . . ? C6 C7 H7 120.9 . . ? C6 C7 C8 118.29(16) . . ? C8 C7 H7 120.9 . . ? N1 C8 C3 106.94(16) . . ? N1 C8 C7 131.53(16) . . ? C7 C8 C3 121.53(15) . . ? O1 C9 C10 104.7(2) . . ? O1 C9 C13 110.0(2) . . ? O1 C9 C14 99.2(2) . . ? O1 C9 C10' 104.4(3) . . ? O1 C9 C13' 99.2(2) . . ? C10 C9 C14 110.2(3) . . ? C13 C9 C10 125.8(3) . . ? C13 C9 C14 103.8(3) . . ? C10' C9 C13' 101.1(4) . . ? C14' C9 O1 120.5(3) . . ? C14' C9 C10' 120.9(4) . . ? C14' C9 C13' 106.9(5) . . ? O1 B1 C5 122.53(15) . . ? O2 B1 O1 112.94(15) . . ? O2 B1 C5 124.53(16) . . ? O2 C10 C11 109.3(3) . . ? O2 C10 C12 106.5(4) . . ? C9 C10 O2 105.1(3) . . ? C9 C10 C11 107.3(4) . . ? C9 C10 C12 118.8(4) . . ? C12 C10 C11 109.6(5) . . ? C10 C11 H11A 109.5 . . ? C10 C11 H11B 109.5 . . ? C10 C11 H11C 109.5 . . ? H11A C11 H11B 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C10 C12 H12A 109.5 . . ? C10 C12 H12B 109.5 . . ? C10 C12 H12C 109.5 . . ? H12A C12 H12B 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C9 C13 H13A 109.5 . . ? C9 C13 H13B 109.5 . . ? C9 C13 H13C 109.5 . . ? H13A C13 H13B 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C9 C14 H14A 109.5 . . ? C9 C14 H14B 109.5 . . ? C9 C14 H14C 109.5 . . ? H14A C14 H14B 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? O2 C10' C9 101.1(4) . . ? O2 C10' C11' 106.0(6) . . ? O2 C10' C12' 111.2(6) . . ? C11' C10' C9 122.0(7) . . ? C12' C10' C9 105.7(6) . . ? C12' C10' C11' 110.4(6) . . ? C10' C11' H11D 109.5 . . ? C10' C11' H11E 109.5 . . ? C10' C11' H11F 109.5 . . ? H11D C11' H11E 109.5 . . ? H11D C11' H11F 109.5 . . ? H11E C11' H11F 109.5 . . ? C10' C12' H12D 109.5 . . ? C10' C12' H12E 109.5 . . ? C10' C12' H12F 109.5 . . ? H12D C12' H12E 109.5 . . ? H12D C12' H12F 109.5 . . ? H12E C12' H12F 109.5 . . ? C9 C13' H13D 109.5 . . ? C9 C13' H13E 109.5 . . ? C9 C13' H13F 109.5 . . ? H13D C13' H13E 109.5 . . ? H13D C13' H13F 109.5 . . ? H13E C13' H13F 109.5 . . ? C9 C14' H14D 109.5 . . ? C9 C14' H14E 109.5 . . ? C9 C14' H14F 109.5 . . ? H14D C14' H14E 109.5 . . ? H14D C14' H14F 109.5 . . ? H14E C14' H14F 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 O1 C9 1.458(2) . ? O1 B1 1.366(2) . ? O2 B1 1.352(2) . ? O2 C10 1.487(5) . ? O2 C10' 1.466(8) . ? N1 H1 0.8600 . ? N1 C1 1.360(3) . ? N1 C8 1.377(2) . ? C1 H1A 0.9300 . ? C1 C2 1.349(3) . ? C2 H2 0.9300 . ? C2 C3 1.433(3) . ? C3 C4 1.398(2) . ? C3 C8 1.405(2) . ? C4 H4 0.9300 . ? C4 C5 1.384(2) . ? C5 C6 1.413(2) . ? C5 B1 1.549(2) . ? C6 H6 0.9300 . ? C6 C7 1.375(3) . ? C7 H7 0.9300 . ? C7 C8 1.386(3) . ? C9 C10 1.461(5) . ? C9 C13 1.460(4) . ? C9 C14 1.675(5) . ? C9 C10' 1.563(9) . ? C9 C13' 1.782(6) . ? C9 C14' 1.351(6) . ? C10 C11 1.532(6) . ? C10 C12 1.491(7) . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 0.9600 . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 0.9600 . ? C10' C11' 1.542(9) . ? C10' C12' 1.511(8) . ? C11' H11D 0.9600 . ? C11' H11E 0.9600 . ? C11' H11F 0.9600 . ? C12' H12D 0.9600 . ? C12' H12E 0.9600 . ? C12' H12F 0.9600 . ? C13' H13D 0.9600 . ? C13' H13E 0.9600 . ? C13' H13F 0.9600 . ? C14' H14D 0.9600 . ? C14' H14E 0.9600 . ? C14' H14F 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 O1 C9 C10 O2 18.6(3) . . . . ? O1 C9 C10 C11 -97.6(3) . . . . ? O1 C9 C10 C12 137.5(4) . . . . ? O1 C9 C10' O2 -20.6(4) . . . . ? O1 C9 C10' C11' -137.6(6) . . . . ? O1 C9 C10' C12' 95.4(5) . . . . ? N1 C1 C2 C3 0.2(3) . . . . ? C1 N1 C8 C3 0.3(2) . . . . ? C1 N1 C8 C7 179.7(2) . . . . ? C1 C2 C3 C4 -179.6(2) . . . . ? C1 C2 C3 C8 0.0(2) . . . . ? C2 C3 C4 C5 179.75(19) . . . . ? C2 C3 C8 N1 -0.2(2) . . . . ? C2 C3 C8 C7 -179.67(17) . . . . ? C3 C4 C5 C6 -0.1(2) . . . . ? C3 C4 C5 B1 179.76(15) . . . . ? C4 C3 C8 N1 179.51(15) . . . . ? C4 C3 C8 C7 0.0(3) . . . . ? C4 C5 C6 C7 -0.1(3) . . . . ? C4 C5 B1 O1 -1.3(3) . . . . ? C4 C5 B1 O2 179.53(16) . . . . ? C5 C6 C7 C8 0.3(3) . . . . ? C6 C5 B1 O1 178.63(16) . . . . ? C6 C5 B1 O2 -0.6(3) . . . . ? C6 C7 C8 N1 -179.57(18) . . . . ? C6 C7 C8 C3 -0.2(3) . . . . ? C8 N1 C1 C2 -0.3(3) . . . . ? C8 C3 C4 C5 0.2(2) . . . . ? C9 O1 B1 O2 0.5(2) . . . . ? C9 O1 B1 C5 -178.78(17) . . . . ? B1 O1 C9 C10 -12.4(3) . . . . ? B1 O1 C9 C13 -150.1(3) . . . . ? B1 O1 C9 C14 101.5(2) . . . . ? B1 O1 C9 C10' 13.1(3) . . . . ? B1 O1 C9 C13' -91.0(3) . . . . ? B1 O1 C9 C14' 153.2(5) . . . . ? B1 O2 C10 C9 -18.6(3) . . . . ? B1 O2 C10 C11 96.2(3) . . . . ? B1 O2 C10 C12 -145.5(4) . . . . ? B1 O2 C10' C9 21.6(4) . . . . ? B1 O2 C10' C11' 149.9(5) . . . . ? B1 O2 C10' C12' -90.2(6) . . . . ? B1 C5 C6 C7 -179.98(17) . . . . ? C10 O2 B1 O1 11.5(3) . . . . ? C10 O2 B1 C5 -169.3(2) . . . . ? C13 C9 C10 O2 147.3(3) . . . . ? C13 C9 C10 C11 31.1(5) . . . . ? C13 C9 C10 C12 -93.8(6) . . . . ? C14 C9 C10 O2 -87.2(3) . . . . ? C14 C9 C10 C11 156.6(3) . . . . ? C14 C9 C10 C12 31.7(6) . . . . ? C10' O2 B1 O1 -15.2(3) . . . . ? C10' O2 B1 C5 164.1(3) . . . . ? C13' C9 C10' O2 82.0(4) . . . . ? C13' C9 C10' C11' -35.0(7) . . . . ? C13' C9 C10' C12' -162.1(5) . . . . ? C14' C9 C10' O2 -160.5(5) . . . . ? C14' C9 C10' C11' 82.5(8) . . . . ? C14' C9 C10' C12' -44.5(7) . . . . ?