#------------------------------------------------------------------------------ #$Date: 2024-06-01 01:14:32 +0300 (Sat, 01 Jun 2024) $ #$Revision: 292134 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/57/17/1571745.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_1571745 loop_ _publ_author_name 'Zhu, Mengjie' 'Wang, Puzhao' 'Wu, Zhengqiu' 'Zhong, Yangfa' 'Su, Laiman' 'Xin, Yuquan' 'Spokoyny, Alex' 'Zou, Chao' 'mu, xin' _publ_section_title ; A Pd-Catalyzed Route to Carborane-Fused Boron Heterocycles ; _journal_name_full 'Chemical Science' _journal_paper_doi 10.1039/D4SC02214A _journal_year 2024 _chemical_formula_moiety 'C7 H9 B5 N2 O4' _chemical_formula_sum 'C7 H9 B5 N2 O4' _chemical_formula_weight 239.21 _space_group_crystal_system monoclinic _space_group_IT_number 15 _space_group_name_Hall '-C 2yc' _space_group_name_H-M_alt 'C 1 2/c 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary dual _audit_creation_date 2023-06-08 _audit_creation_method ; Olex2 1.5 (compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748) ; _audit_update_record ; 2024-01-04 deposited with the CCDC. 2024-05-28 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 100.8020(10) _cell_angle_gamma 90 _cell_formula_units_Z 8 _cell_length_a 15.2441(3) _cell_length_b 11.0252(2) _cell_length_c 12.8370(3) _cell_measurement_reflns_used 6036 _cell_measurement_temperature 213.00 _cell_measurement_theta_max 54.783 _cell_measurement_theta_min 3.050 _cell_volume 2119.28(8) _computing_cell_refinement 'SAINT v8.37A (Bruker, 2015)' _computing_data_reduction 'SAINT v8.37A (Bruker, 2015)' _computing_molecular_graphics 'Olex2 1.5 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 1.5 (Dolomanov et al., 2009)' _computing_structure_refinement 'SHELXL 2018/3 (Sheldrick, 2015)' _computing_structure_solution 'SHELXT 2018/2 (Sheldrick, 2018)' _diffrn_ambient_temperature 213.00 _diffrn_measured_fraction_theta_full 0.980 _diffrn_measured_fraction_theta_max 0.980 _diffrn_measurement_device_type 'Bruker D8 Venture' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_type GaK\a _diffrn_radiation_wavelength 1.34139 _diffrn_reflns_av_R_equivalents 0.0479 _diffrn_reflns_av_unetI/netI 0.0382 _diffrn_reflns_Laue_measured_fraction_full 0.980 _diffrn_reflns_Laue_measured_fraction_max 0.980 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_number 9005 _diffrn_reflns_point_group_measured_fraction_full 0.980 _diffrn_reflns_point_group_measured_fraction_max 0.980 _diffrn_reflns_theta_full 53.594 _diffrn_reflns_theta_max 54.941 _diffrn_reflns_theta_min 5.015 _diffrn_source_current 2.85 _diffrn_source_power 0.19887300000000002 _diffrn_source_voltage 69.78 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.578 _exptl_absorpt_correction_T_max 0.7508 _exptl_absorpt_correction_T_min 0.5428 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1187 before and 0.0696 after correction. The Ratio of minimum to maximum transmission is 0.7230. The \l/2 correction factor is Not present. ; _exptl_crystal_colour red _exptl_crystal_colour_primary red _exptl_crystal_density_diffrn 1.499 _exptl_crystal_description block _exptl_crystal_F_000 976 _exptl_crystal_size_max 0.07 _exptl_crystal_size_mid 0.07 _exptl_crystal_size_min 0.05 _refine_diff_density_max 0.213 _refine_diff_density_min -0.225 _refine_diff_density_rms 0.042 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.056 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 164 _refine_ls_number_reflns 1974 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.056 _refine_ls_R_factor_all 0.0502 _refine_ls_R_factor_gt 0.0457 _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^)+(0.0714P)^2^+1.3868P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1265 _refine_ls_wR_factor_ref 0.1308 _reflns_Friedel_coverage 0.000 _reflns_number_gt 1777 _reflns_number_total 1974 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d4sc02214a2.cif _cod_data_source_block mj23379_0m _cod_database_code 1571745 _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_max 0.972 _shelx_estimated_absorpt_t_min 0.961 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All B(H) groups, All C(H) groups At 1.5 times of: All C(H,H,H) groups 2.a Aromatic/amide H refined with riding coordinates: C4(H4A) 2.b Idealised Me refined as rotating group: C7(H7A,H7B,H7C) 2.c Boron cage BH refined with riding coordinates: B1(H1), C1(H1A), B2(H2), B3(H3), B4(H4) ; _shelx_res_file ; TITL mj23379_0m_a.res in C2/c mj23379_0m.res created by SHELXL-2018/3 at 14:43:19 on 08-Jun-2023 REM Old TITL mj23379_0m in C2/c REM SHELXT solution in C2/c: R1 0.153, Rweak 0.005, Alpha 0.038 REM 1.430 for 112 systematic absences, Orientation as input REM Formula found by SHELXT: C8 B5 N2 O3 CELL 1.34139 15.2441 11.0252 12.837 90 100.802 90 ZERR 8 0.0003 0.0002 0.0003 0 0.001 0 LATT 7 SYMM -X,+Y,0.5-Z SFAC C H B N O DISP B 0.007 0.0029 26.6 DISP C 0.0137 0.0067 57.1 DISP H -0 0 0.6481 DISP N 0.0241 0.0134 109.9 DISP O 0.0389 0.0241 193.4 UNIT 56 72 40 16 32 L.S. 4 PLAN 5 SIZE 0.05 0.07 0.07 TEMP -60.15 CONF BOND list 4 fmap 2 MORE -1 BOND $H ACTA REM REM REM WGHT 0.071400 1.386800 FVAR 0.88002 B1 3 0.469389 0.876870 0.803215 11.00000 0.04250 0.02951 = 0.05785 -0.00411 0.02037 -0.00019 AFIX 153 H1 2 0.449443 0.962588 0.837708 11.00000 -1.20000 AFIX 0 C1 1 0.574353 0.822239 0.818986 11.00000 0.03629 0.03498 = 0.05027 -0.00898 0.01192 -0.00603 AFIX 153 H1A 2 0.628124 0.876203 0.868299 11.00000 -1.20000 AFIX 0 N1 4 0.559810 0.493337 0.668050 11.00000 0.03995 0.02835 = 0.03398 -0.00008 0.01422 0.00010 O1 5 0.635946 0.630697 0.508882 11.00000 0.07766 0.04807 = 0.06570 0.01831 0.03709 0.01325 B2 3 0.501063 0.749000 0.883951 11.00000 0.03780 0.03387 = 0.04014 -0.00715 0.01011 -0.00269 AFIX 153 H2 2 0.502866 0.750012 0.970791 11.00000 -1.20000 AFIX 0 C2 1 0.538078 0.393803 0.723655 11.00000 0.03783 0.02692 = 0.03167 -0.00111 0.00972 -0.00134 N2 4 0.613081 0.190157 0.770232 11.00000 0.03780 0.02978 = 0.04630 -0.00004 0.00651 0.00048 O2 5 0.746559 0.493413 0.530441 11.00000 0.04497 0.05174 = 0.04441 0.00070 0.02161 -0.00382 B3 3 0.582001 0.669846 0.826770 11.00000 0.03298 0.03460 = 0.03654 -0.00165 0.00533 0.00235 AFIX 153 H3 2 0.636752 0.619301 0.877859 11.00000 -1.20000 AFIX 0 C3 1 0.600449 0.304035 0.714975 11.00000 0.03693 0.02868 = 0.03589 -0.00125 0.00780 0.00027 O3 5 0.672130 0.123542 0.748297 11.00000 0.05637 0.04033 = 0.09380 0.00999 0.02543 0.01612 B4 3 0.600342 0.748695 0.711363 11.00000 0.03280 0.03194 = 0.04402 -0.00153 0.01145 -0.00139 AFIX 153 H4 2 0.666708 0.749335 0.687615 11.00000 -1.20000 AFIX 0 C4 1 0.658699 0.345930 0.651378 11.00000 0.03596 0.03476 = 0.04097 -0.00430 0.01144 0.00208 AFIX 43 H4A 2 0.706081 0.302671 0.631478 11.00000 -1.20000 AFIX 0 O4 5 0.568279 0.165431 0.836938 11.00000 0.05649 0.04329 = 0.04779 0.01062 0.01179 0.00249 B5 3 0.530825 0.618313 0.696953 11.00000 0.03450 0.02735 = 0.03258 0.00073 0.00909 0.00031 C5 1 0.633489 0.462252 0.623562 11.00000 0.03787 0.03425 = 0.03312 -0.00365 0.01228 -0.00187 C6 1 0.670264 0.540487 0.549902 11.00000 0.04707 0.03746 = 0.03628 -0.00521 0.01638 -0.00423 C7 1 0.787736 0.559015 0.454861 11.00000 0.05952 0.06832 = 0.05117 0.00063 0.02969 -0.01516 AFIX 137 H7A 2 0.747791 0.559663 0.386486 11.00000 -1.50000 H7B 2 0.843334 0.519734 0.448115 11.00000 -1.50000 H7C 2 0.799731 0.641700 0.479230 11.00000 -1.50000 AFIX 0 HKLF 4 REM mj23379_0m_a.res in C2/c REM wR2 = 0.1308, GooF = S = 1.056, Restrained GooF = 1.056 for all data REM R1 = 0.0457 for 1777 Fo > 4sig(Fo) and 0.0502 for all 1974 data REM 164 parameters refined using 0 restraints END WGHT 0.0714 1.3868 REM Highest difference peak 0.213, deepest hole -0.225, 1-sigma level 0.042 Q1 1 0.5000 0.3917 0.7500 10.50000 0.05 0.21 Q2 1 0.6595 0.4942 0.5964 11.00000 0.05 0.21 Q3 1 0.6384 0.3983 0.6143 11.00000 0.05 0.19 Q4 1 0.8046 0.4848 0.4103 11.00000 0.05 0.19 Q5 1 0.5983 0.8615 0.8394 11.00000 0.05 0.18 ; _shelx_res_checksum 78804 _olex2_submission_special_instructions 'No special instructions were received' loop_ _space_group_symop_operation_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' 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 B1 B 0.46939(13) 0.87687(16) 0.80321(17) 0.0419(5) Uani 1 1 d . . . . . H1 H 0.449443 0.962588 0.837708 0.050 Uiso 1 1 calc R U . . . C1 C 0.57435(11) 0.82224(15) 0.81899(14) 0.0400(4) Uani 1 1 d . . . . . H1A H 0.628124 0.876203 0.868299 0.048 Uiso 1 1 calc R U . . . N1 N 0.55981(9) 0.49334(11) 0.66805(10) 0.0331(3) Uani 1 1 d . . . . . O1 O 0.63595(10) 0.63070(13) 0.50888(12) 0.0607(4) Uani 1 1 d . . . . . B2 B 0.50106(12) 0.74900(16) 0.88395(15) 0.0369(4) Uani 1 1 d . . . . . H2 H 0.502866 0.750012 0.970791 0.044 Uiso 1 1 calc R U . . . C2 C 0.53808(10) 0.39380(13) 0.72366(12) 0.0317(4) Uani 1 1 d . . . . . N2 N 0.61308(9) 0.19016(12) 0.77023(11) 0.0381(4) Uani 1 1 d . . . . . O2 O 0.74656(8) 0.49341(11) 0.53044(10) 0.0453(3) Uani 1 1 d . . . . . B3 B 0.58200(11) 0.66985(16) 0.82677(14) 0.0349(4) Uani 1 1 d . . . . . H3 H 0.636752 0.619301 0.877859 0.042 Uiso 1 1 calc R U . . . C3 C 0.60045(10) 0.30404(14) 0.71497(12) 0.0337(4) Uani 1 1 d . . . . . O3 O 0.67213(9) 0.12354(12) 0.74830(14) 0.0620(4) Uani 1 1 d . . . . . B4 B 0.60034(12) 0.74870(15) 0.71136(15) 0.0357(4) Uani 1 1 d . . . . . H4 H 0.666708 0.749335 0.687615 0.043 Uiso 1 1 calc R U . . . C4 C 0.65870(10) 0.34593(15) 0.65138(13) 0.0367(4) Uani 1 1 d . . . . . H4A H 0.706081 0.302671 0.631478 0.044 Uiso 1 1 calc R U . . . O4 O 0.56828(9) 0.16543(11) 0.83694(10) 0.0489(4) Uani 1 1 d . . . . . B5 B 0.53083(11) 0.61831(15) 0.69695(13) 0.0311(4) Uani 1 1 d . . . . . C5 C 0.63349(10) 0.46225(14) 0.62356(12) 0.0344(4) Uani 1 1 d . . . . . C6 C 0.67026(12) 0.54049(15) 0.54990(13) 0.0392(4) Uani 1 1 d . . . . . C7 C 0.78774(14) 0.5590(2) 0.45486(16) 0.0572(5) Uani 1 1 d . . . . . H7A H 0.747791 0.559663 0.386486 0.086 Uiso 1 1 calc R U . . . H7B H 0.843334 0.519734 0.448115 0.086 Uiso 1 1 calc R U . . . H7C H 0.799731 0.641700 0.479230 0.086 Uiso 1 1 calc R U . . . 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 B1 0.0425(10) 0.0295(9) 0.0578(12) -0.0041(8) 0.0204(9) -0.0002(7) C1 0.0363(8) 0.0350(9) 0.0503(10) -0.0090(7) 0.0119(7) -0.0060(6) N1 0.0400(7) 0.0283(7) 0.0340(7) -0.0001(5) 0.0142(6) 0.0001(5) O1 0.0777(10) 0.0481(8) 0.0657(9) 0.0183(7) 0.0371(8) 0.0132(7) B2 0.0378(9) 0.0339(9) 0.0401(10) -0.0071(7) 0.0101(8) -0.0027(7) C2 0.0378(8) 0.0269(7) 0.0317(7) -0.0011(6) 0.0097(6) -0.0013(6) N2 0.0378(7) 0.0298(7) 0.0463(8) 0.0000(6) 0.0065(6) 0.0005(5) O2 0.0450(7) 0.0517(8) 0.0444(7) 0.0007(5) 0.0216(6) -0.0038(5) B3 0.0330(9) 0.0346(9) 0.0365(9) -0.0016(7) 0.0053(7) 0.0023(7) C3 0.0369(8) 0.0287(8) 0.0359(8) -0.0012(6) 0.0078(6) 0.0003(6) O3 0.0564(8) 0.0403(7) 0.0938(11) 0.0100(7) 0.0254(8) 0.0161(6) B4 0.0328(9) 0.0319(9) 0.0440(10) -0.0015(7) 0.0115(8) -0.0014(7) C4 0.0360(8) 0.0348(8) 0.0410(9) -0.0043(6) 0.0114(7) 0.0021(6) O4 0.0565(8) 0.0433(7) 0.0478(7) 0.0106(5) 0.0118(6) 0.0025(6) B5 0.0345(9) 0.0274(8) 0.0326(9) 0.0007(6) 0.0091(7) 0.0003(6) C5 0.0379(8) 0.0343(8) 0.0331(8) -0.0037(6) 0.0123(6) -0.0019(6) C6 0.0471(9) 0.0375(9) 0.0363(8) -0.0052(7) 0.0164(7) -0.0042(7) C7 0.0595(12) 0.0683(13) 0.0512(11) 0.0006(9) 0.0297(9) -0.0152(10) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0137 0.0067 '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 0.0070 0.0029 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0241 0.0134 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0389 0.0241 '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 B1 H1 121.6 2_656 . ? C1 B1 B1 57.71(12) 2_656 2_656 ? C1 B1 B1 58.25(11) . 2_656 ? C1 B1 H1 125.6 2_656 . ? C1 B1 H1 125.5 . . ? C1 B1 C1 100.60(13) . 2_656 ? C1 B1 B2 59.63(11) . . ? C1 B1 B2 106.06(12) 2_656 . ? C1 B1 B4 59.39(10) 2_656 2_656 ? C1 B1 B4 105.49(12) . 2_656 ? B2 B1 B1 108.88(11) . 2_656 ? B2 B1 H1 120.8 . . ? B4 B1 B1 108.04(12) 2_656 2_656 ? B4 B1 H1 121.4 2_656 . ? B4 B1 B2 60.85(10) 2_656 . ? B1 C1 B1 64.04(13) . 2_656 ? B1 C1 H1A 117.4 . . ? B1 C1 H1A 117.2 2_656 . ? B1 C1 B2 115.96(13) 2_656 . ? B1 C1 B2 62.41(10) . . ? B1 C1 B4 62.09(11) 2_656 . ? B1 C1 B4 115.49(14) . . ? B2 C1 H1A 117.0 . . ? B3 C1 B1 114.81(13) . 2_656 ? B3 C1 B1 114.63(12) . . ? B3 C1 H1A 117.7 . . ? B3 C1 B2 63.02(10) . . ? B3 C1 B4 63.37(10) . . ? B4 C1 H1A 117.2 . . ? B4 C1 B2 116.09(12) . . ? C2 N1 B5 119.11(12) . . ? C2 N1 C5 107.79(12) . . ? C5 N1 B5 128.19(13) . . ? B1 B2 H2 122.3 . . ? B1 B2 B3 106.53(13) . . ? B1 B2 B4 59.42(11) . 2_656 ? B1 B2 B5 106.74(13) . 2_656 ? C1 B2 B1 57.96(10) . . ? C1 B2 H2 126.0 . . ? C1 B2 B3 57.66(10) . . ? C1 B2 B4 103.13(13) . 2_656 ? C1 B2 B5 103.16(12) . 2_656 ? B3 B2 H2 122.1 . . ? B3 B2 B4 107.17(12) . 2_656 ? B3 B2 B5 59.95(10) . 2_656 ? B4 B2 H2 123.0 2_656 . ? B4 B2 B5 59.59(10) 2_656 2_656 ? B5 B2 H2 123.0 2_656 . ? N1 C2 C2 122.10(10) . 2_656 ? N1 C2 C3 106.84(13) . . ? C3 C2 C2 131.05(10) . 2_656 ? O3 N2 C3 116.30(14) . . ? O4 N2 C3 120.00(13) . . ? O4 N2 O3 123.66(14) . . ? C6 O2 C7 115.67(15) . . ? C1 B3 B2 59.32(10) . . ? C1 B3 H3 124.8 . . ? C1 B3 B4 59.01(10) . . ? C1 B3 B5 104.70(12) . 2_656 ? C1 B3 B5 104.32(13) . . ? B2 B3 H3 120.4 . . ? B2 B3 B4 109.42(13) . . ? B2 B3 B5 108.91(12) . . ? B2 B3 B5 60.33(9) . 2_656 ? B4 B3 H3 121.2 . . ? B4 B3 B5 59.46(10) . . ? B5 B3 H3 122.4 2_656 . ? B5 B3 H3 122.5 . . ? B5 B3 B4 108.04(12) 2_656 . ? B5 B3 B5 60.19(11) 2_656 . ? C2 C3 N2 127.76(14) . . ? C2 C3 C4 109.35(14) . . ? C4 C3 N2 122.54(14) . . ? B1 B4 B2 59.73(11) 2_656 2_656 ? B1 B4 B3 107.13(12) 2_656 . ? B1 B4 H4 122.0 2_656 . ? B1 B4 B5 107.63(12) 2_656 . ? C1 B4 B1 58.53(11) . 2_656 ? C1 B4 B2 104.54(12) . 2_656 ? C1 B4 B3 57.62(10) . . ? C1 B4 H4 125.4 . . ? C1 B4 B5 104.11(12) . . ? B2 B4 B3 108.67(12) 2_656 . ? B2 B4 H4 122.0 2_656 . ? B3 B4 H4 121.6 . . ? B5 B4 B2 60.39(10) . 2_656 ? B5 B4 B3 60.56(10) . . ? B5 B4 H4 122.3 . . ? C3 C4 H4A 126.7 . . ? C5 C4 C3 106.58(13) . . ? C5 C4 H4A 126.7 . . ? N1 B5 B2 130.58(13) . 2_656 ? N1 B5 B3 124.38(13) . 2_656 ? N1 B5 B3 114.81(13) . . ? N1 B5 B4 124.51(13) . . ? N1 B5 B5 113.86(8) . 2_656 ? B2 B5 B3 107.91(12) 2_656 . ? B2 B5 B5 108.46(10) 2_656 2_656 ? B3 B5 B2 59.72(10) 2_656 2_656 ? B3 B5 B3 107.17(12) 2_656 . ? B3 B5 B5 60.24(11) 2_656 2_656 ? B4 B5 B2 60.02(10) . 2_656 ? B4 B5 B3 107.32(12) . 2_656 ? B4 B5 B3 59.98(10) . . ? B4 B5 B5 107.96(10) . 2_656 ? B5 B5 B3 59.57(11) 2_656 . ? N1 C5 C6 123.63(15) . . ? C4 C5 N1 109.40(13) . . ? C4 C5 C6 126.69(15) . . ? O1 C6 O2 124.22(15) . . ? O1 C6 C5 125.67(16) . . ? O2 C6 C5 110.04(15) . . ? O2 C7 H7A 109.5 . . ? O2 C7 H7B 109.5 . . ? O2 C7 H7C 109.5 . . ? H7A C7 H7B 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 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 B1 B1 1.793(4) 2_656 ? B1 H1 1.1100 . ? B1 C1 1.686(2) . ? B1 C1 1.696(3) 2_656 ? B1 B2 1.763(3) . ? B1 B4 1.757(3) 2_656 ? C1 H1A 1.1100 . ? C1 B2 1.716(2) . ? C1 B3 1.686(3) . ? C1 B4 1.711(2) . ? N1 C2 1.3828(19) . ? N1 B5 1.514(2) . ? N1 C5 1.3948(19) . ? O1 C6 1.199(2) . ? B2 H2 1.1100 . ? B2 B3 1.778(2) . ? B2 B4 1.783(3) 2_656 ? B2 B5 1.789(2) 2_656 ? C2 C2 1.449(3) 2_656 ? C2 C3 1.391(2) . ? N2 C3 1.437(2) . ? N2 O3 1.2345(18) . ? N2 O4 1.2220(18) . ? O2 C6 1.339(2) . ? O2 C7 1.445(2) . ? B3 H3 1.1100 . ? B3 B4 1.784(3) . ? B3 B5 1.783(2) 2_656 ? B3 B5 1.795(2) . ? C3 C4 1.393(2) . ? B4 H4 1.1100 . ? B4 B5 1.775(2) . ? C4 H4A 0.9400 . ? C4 C5 1.367(2) . ? B5 B5 1.794(3) 2_656 ? C5 C6 1.467(2) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C7 H7C 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 _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag B1 B1 C1 B2 -143.49(12) 2_656 . . . ? B1 B1 C1 B3 -106.87(14) 2_656 . . . ? B1 B1 C1 B4 -36.00(10) 2_656 . . . ? B1 B1 B2 C1 32.33(14) 2_656 . . . ? B1 B1 B2 B3 -0.1(2) 2_656 . . . ? B1 B1 B2 B4 -100.61(17) 2_656 . . 2_656 ? B1 B1 B2 B5 -62.96(18) 2_656 . . 2_656 ? B1 C1 B2 B1 -36.51(13) 2_656 . . . ? B1 C1 B2 B3 106.01(15) 2_656 . . . ? B1 C1 B2 B3 142.53(14) . . . . ? B1 C1 B2 B4 3.82(17) 2_656 . . 2_656 ? B1 C1 B2 B4 40.33(12) . . . 2_656 ? B1 C1 B2 B5 65.18(16) 2_656 . . 2_656 ? B1 C1 B2 B5 101.69(14) . . . 2_656 ? B1 C1 B3 B2 -107.80(15) 2_656 . . . ? B1 C1 B3 B2 -36.38(14) . . . . ? B1 C1 B3 B4 36.03(13) 2_656 . . . ? B1 C1 B3 B4 107.45(15) . . . . ? B1 C1 B3 B5 -66.45(16) 2_656 . . 2_656 ? B1 C1 B3 B5 67.36(16) . . . . ? B1 C1 B3 B5 -4.06(17) 2_656 . . . ? B1 C1 B3 B5 4.97(18) . . . 2_656 ? B1 C1 B4 B1 36.73(12) . . . 2_656 ? B1 C1 B4 B2 -39.70(12) 2_656 . . 2_656 ? B1 C1 B4 B2 -2.97(17) . . . 2_656 ? B1 C1 B4 B3 -142.83(13) 2_656 . . . ? B1 C1 B4 B3 -106.10(14) . . . . ? B1 C1 B4 B5 -102.25(13) 2_656 . . . ? B1 C1 B4 B5 -65.51(16) . . . . ? B1 B2 B3 C1 32.55(12) . . . . ? B1 B2 B3 B4 0.10(17) . . . . ? B1 B2 B3 B5 -63.23(15) . . . . ? B1 B2 B3 B5 -100.10(13) . . . 2_656 ? B1 B4 B5 N1 158.90(15) 2_656 . . . ? B1 B4 B5 B2 37.92(12) 2_656 . . 2_656 ? B1 B4 B5 B3 -100.11(14) 2_656 . . . ? B1 B4 B5 B3 0.09(16) 2_656 . . 2_656 ? B1 B4 B5 B5 -63.46(17) 2_656 . . 2_656 ? C1 B1 C1 B1 40.98(15) 2_656 . . 2_656 ? C1 B1 C1 B2 -102.51(12) 2_656 . . . ? C1 B1 C1 B3 -65.89(15) 2_656 . . . ? C1 B1 C1 B4 4.97(18) 2_656 . . . ? C1 B1 B2 C1 93.05(13) 2_656 . . . ? C1 B1 B2 B3 60.62(15) 2_656 . . . ? C1 B1 B2 B3 -32.43(12) . . . . ? C1 B1 B2 B4 -39.88(12) 2_656 . . 2_656 ? C1 B1 B2 B4 -132.93(13) . . . 2_656 ? C1 B1 B2 B5 -95.29(13) . . . 2_656 ? C1 B1 B2 B5 -2.24(16) 2_656 . . 2_656 ? C1 B2 B3 B4 -32.44(12) . . . . ? C1 B2 B3 B5 -95.78(14) . . . . ? C1 B2 B3 B5 -132.65(13) . . . 2_656 ? C1 B3 B4 B1 -32.63(12) . . . 2_656 ? C1 B3 B4 B2 -95.71(13) . . . 2_656 ? C1 B3 B4 B5 -133.58(13) . . . . ? C1 B3 B5 N1 156.85(12) . . . . ? C1 B3 B5 B2 2.36(15) . . . 2_656 ? C1 B3 B5 B3 -60.59(13) . . . 2_656 ? C1 B3 B5 B4 39.86(11) . . . . ? C1 B3 B5 B5 -98.95(11) . . . 2_656 ? C1 B4 B5 N1 -140.11(15) . . . . ? C1 B4 B5 B2 98.91(13) . . . 2_656 ? C1 B4 B5 B3 61.08(15) . . . 2_656 ? C1 B4 B5 B3 -39.11(11) . . . . ? C1 B4 B5 B5 -2.47(17) . . . 2_656 ? N1 C2 C3 N2 171.18(14) . . . . ? N1 C2 C3 C4 -2.03(17) . . . . ? N1 C5 C6 O1 -10.3(3) . . . . ? N1 C5 C6 O2 172.76(14) . . . . ? B2 B1 C1 B1 143.49(12) . . . 2_656 ? B2 B1 C1 B3 36.62(14) . . . . ? B2 B1 C1 B4 107.48(14) . . . . ? B2 C1 B3 B4 143.83(13) . . . . ? B2 C1 B3 B5 41.36(12) . . . 2_656 ? B2 C1 B3 B5 103.74(13) . . . . ? B2 C1 B4 B1 106.99(15) . . . 2_656 ? B2 C1 B4 B2 67.28(15) . . . 2_656 ? B2 C1 B4 B3 -35.85(13) . . . . ? B2 C1 B4 B5 4.74(17) . . . . ? B2 B3 B4 B1 -0.07(17) . . . 2_656 ? B2 B3 B4 C1 32.56(12) . . . . ? B2 B3 B4 B2 -63.15(14) . . . 2_656 ? B2 B3 B4 B5 -101.02(13) . . . . ? B2 B3 B5 N1 -141.13(13) . . . . ? B2 B3 B5 B2 64.37(16) . . . 2_656 ? B2 B3 B5 B3 1.43(18) . . . 2_656 ? B2 B3 B5 B4 101.88(14) . . . . ? B2 B3 B5 B5 -36.94(9) . . . 2_656 ? B2 B4 B5 N1 120.98(17) 2_656 . . . ? B2 B4 B5 B3 -138.02(13) 2_656 . . . ? B2 B4 B5 B3 -37.83(12) 2_656 . . 2_656 ? B2 B4 B5 B5 -101.38(14) 2_656 . . 2_656 ? C2 N1 B5 B2 -147.06(15) . . . 2_656 ? C2 N1 B5 B3 65.59(18) . . . . ? C2 N1 B5 B3 -69.7(2) . . . 2_656 ? C2 N1 B5 B4 135.04(15) . . . . ? C2 N1 B5 B5 -0.5(2) . . . 2_656 ? C2 N1 C5 C4 -0.71(18) . . . . ? C2 N1 C5 C6 173.56(15) . . . . ? C2 C2 C3 N2 -9.8(3) 2_656 . . . ? C2 C2 C3 C4 177.0(2) 2_656 . . . ? C2 C3 C4 C5 1.59(18) . . . . ? N2 C3 C4 C5 -172.04(14) . . . . ? B3 C1 B2 B1 -142.53(14) . . . . ? B3 C1 B2 B4 -102.19(13) . . . 2_656 ? B3 C1 B2 B5 -40.83(12) . . . 2_656 ? B3 C1 B4 B1 142.83(13) . . . 2_656 ? B3 C1 B4 B2 103.13(12) . . . 2_656 ? B3 C1 B4 B5 40.58(11) . . . . ? B3 B4 B5 N1 -101.00(16) . . . . ? B3 B4 B5 B2 138.02(13) . . . 2_656 ? B3 B4 B5 B3 100.19(12) . . . 2_656 ? B3 B4 B5 B5 36.65(13) . . . 2_656 ? C3 C4 C5 N1 -0.53(18) . . . . ? C3 C4 C5 C6 -174.59(16) . . . . ? O3 N2 C3 C2 178.85(15) . . . . ? O3 N2 C3 C4 -8.8(2) . . . . ? B4 B1 C1 B1 101.92(15) 2_656 . . 2_656 ? B4 B1 C1 B2 -41.57(12) 2_656 . . . ? B4 B1 C1 B3 -4.96(19) 2_656 . . . ? B4 B1 C1 B4 65.91(18) 2_656 . . . ? B4 B1 B2 C1 132.93(13) 2_656 . . . ? B4 B1 B2 B3 100.51(13) 2_656 . . . ? B4 B1 B2 B5 37.64(11) 2_656 . . 2_656 ? B4 C1 B2 B1 -106.55(15) . . . . ? B4 C1 B2 B3 35.97(13) . . . . ? B4 C1 B2 B4 -66.22(15) . . . 2_656 ? B4 C1 B2 B5 -4.86(18) . . . 2_656 ? B4 C1 B3 B2 -143.83(13) . . . . ? B4 C1 B3 B5 -102.47(13) . . . 2_656 ? B4 C1 B3 B5 -40.08(11) . . . . ? B4 B2 B3 C1 94.92(13) 2_656 . . . ? B4 B2 B3 B4 62.47(14) 2_656 . . . ? B4 B2 B3 B5 -0.86(16) 2_656 . . . ? B4 B2 B3 B5 -37.73(11) 2_656 . . 2_656 ? B4 B3 B5 N1 116.99(14) . . . . ? B4 B3 B5 B2 -37.50(11) . . . 2_656 ? B4 B3 B5 B3 -100.45(11) . . . 2_656 ? B4 B3 B5 B5 -138.81(11) . . . 2_656 ? C4 C5 C6 O1 163.00(18) . . . . ? C4 C5 C6 O2 -14.0(2) . . . . ? O4 N2 C3 C2 -3.2(2) . . . . ? O4 N2 C3 C4 169.22(14) . . . . ? B5 N1 C2 C2 25.3(3) . . . 2_656 ? B5 N1 C2 C3 -155.54(14) . . . . ? B5 N1 C5 C4 153.78(15) . . . . ? B5 N1 C5 C6 -32.0(2) . . . . ? B5 B2 B3 C1 132.65(13) 2_656 . . . ? B5 B2 B3 B4 100.21(13) 2_656 . . . ? B5 B2 B3 B5 36.87(11) 2_656 . . . ? B5 B3 B4 B1 64.01(15) 2_656 . . 2_656 ? B5 B3 B4 B1 100.95(13) . . . 2_656 ? B5 B3 B4 C1 133.58(13) . . . . ? B5 B3 B4 C1 96.64(13) 2_656 . . . ? B5 B3 B4 B2 37.87(11) . . . 2_656 ? B5 B3 B4 B2 0.93(16) 2_656 . . 2_656 ? B5 B3 B4 B5 -36.94(11) 2_656 . . . ? B5 B3 B5 N1 -104.20(10) 2_656 . . . ? B5 B3 B5 B2 101.31(12) 2_656 . . 2_656 ? B5 B3 B5 B3 38.36(14) 2_656 . . 2_656 ? B5 B3 B5 B4 138.81(11) 2_656 . . . ? C5 N1 C2 C2 -177.47(17) . . . 2_656 ? C5 N1 C2 C3 1.66(17) . . . . ? C5 N1 B5 B2 60.9(2) . . . 2_656 ? C5 N1 B5 B3 -86.41(18) . . . . ? C5 N1 B5 B3 138.32(16) . . . 2_656 ? C5 N1 B5 B4 -17.0(2) . . . . ? C5 N1 B5 B5 -152.47(16) . . . 2_656 ? C7 O2 C6 O1 0.2(3) . . . . ? C7 O2 C6 C5 177.23(14) . . . . ?