#------------------------------------------------------------------------------ #$Date: 2023-03-19 01:49:00 +0200 (Sun, 19 Mar 2023) $ #$Revision: 281942 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/71/26/7712655.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_7712655 loop_ _publ_author_name 'Jiang, Xiue' 'Yang, Yalin' 'Du, Huiying' 'Yang, Bo' 'Tang, Pengfei' 'Wu, Bo' 'Ma, Congming' _publ_section_title ; Triazene Bridged Energetic Materials Based on Nitrotriazole: Synthesis, Characterization and Laser Ignited Combustion Performance ; _journal_name_full 'Dalton Transactions' _journal_paper_doi 10.1039/D2DT04007G _journal_year 2023 _chemical_formula_moiety 'C8 H12 K6 N22 O14, H2 O' _chemical_formula_sum 'C8 H14 K6 N22 O15' _chemical_formula_weight 893.01 _space_group_crystal_system monoclinic _space_group_IT_number 13 _space_group_name_Hall '-P 2yc' _space_group_name_H-M_alt 'P 1 2/c 1' _atom_sites_solution_hydrogens difmap _atom_sites_solution_primary dual _audit_creation_date 2022-06-08 _audit_creation_method ; Olex2 1.5 (compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498) ; _audit_update_record ; 2022-12-12 deposited with the CCDC. 2023-03-17 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 106.260(2) _cell_angle_gamma 90 _cell_formula_units_Z 2 _cell_length_a 12.0707(5) _cell_length_b 7.3415(3) _cell_length_c 18.2512(7) _cell_measurement_reflns_used 5972 _cell_measurement_temperature 150.00 _cell_measurement_theta_max 56.876 _cell_measurement_theta_min 3.318 _cell_volume 1552.67(11) _computing_cell_refinement 'SAINT V8.38A (Bruker, 2018)' _computing_data_collection 'Bruker SMART APEX II diffractrometer' _computing_data_reduction 'SAINT V8.38A (Bruker, 2018)' _computing_molecular_graphics 'Olex2 1.5 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 1.5 (Dolomanov et al., 2009)' _computing_structure_refinement 'SHELXL 2019/2 (Sheldrick, 2015)' _computing_structure_solution 'SHELXT 2018/2 (Sheldrick, 2018)' _diffrn_ambient_temperature 150.00 _diffrn_detector 'CCD area detector' _diffrn_measured_fraction_theta_full 0.997 _diffrn_measured_fraction_theta_max 0.996 _diffrn_measurement_device 'three-circle diffractometer' _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_radiation_type GaK\a _diffrn_radiation_wavelength 1.34139 _diffrn_reflns_av_R_equivalents 0.0582 _diffrn_reflns_av_unetI/netI 0.0527 _diffrn_reflns_Laue_measured_fraction_full 0.997 _diffrn_reflns_Laue_measured_fraction_max 0.996 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_k_min -5 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_number 12463 _diffrn_reflns_point_group_measured_fraction_full 0.997 _diffrn_reflns_point_group_measured_fraction_max 0.996 _diffrn_reflns_theta_full 53.594 _diffrn_reflns_theta_max 56.933 _diffrn_reflns_theta_min 3.318 _diffrn_source 'sealed X-ray tube' _diffrn_source_current 2.86 _diffrn_source_power 0.1997996 _diffrn_source_target Mo _diffrn_source_voltage 69.86 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 5.652 _exptl_absorpt_correction_T_max 0.7512 _exptl_absorpt_correction_T_min 0.5035 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1821 before and 0.0600 after correction. The Ratio of minimum to maximum transmission is 0.6703. The \l/2 correction factor is Not present. ; _exptl_crystal_colour 'clear light red' _exptl_crystal_colour_lustre clear _exptl_crystal_colour_modifier light _exptl_crystal_colour_primary red _exptl_crystal_density_diffrn 1.910 _exptl_crystal_description block _exptl_crystal_F_000 900 _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.13 _refine_diff_density_max 0.618 _refine_diff_density_min -0.591 _refine_diff_density_rms 0.091 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.045 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 256 _refine_ls_number_reflns 3165 _refine_ls_number_restraints 11 _refine_ls_restrained_S_all 1.044 _refine_ls_R_factor_all 0.0681 _refine_ls_R_factor_gt 0.0508 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0639P)^2^+2.7858P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1312 _refine_ls_wR_factor_ref 0.1401 _reflns_Friedel_coverage 0.000 _reflns_number_gt 2506 _reflns_number_total 3165 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d2dt04007g2.cif _cod_data_source_block 6 _cod_database_code 7712655 _shelx_shelxl_version_number 2019/2 _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 0.527 _shelx_estimated_absorpt_t_min 0.429 _olex2_refinement_description ; 1. Fixed Uiso At 1.5 times of: All O(H,H) groups, H9 of O9 At 1.2 times of: H7 of O7 2. Restrained distances K2-O6A \\sim K2-O6 with sigma of 0.02 3. Uiso/Uaniso restraints and constraints O6A \\sim O6: within 2A with sigma of 0.01 and sigma for terminal atoms of 0.02 within 2A 4. Rigid body (RIGU) restrains K2, O6 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002 K2, O6A with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002 5. Others Sof(K3A)=1-FVAR(1) Sof(K3)=FVAR(1) Sof(O6A)=Sof(H6AA)=Sof(H6AB)=1-FVAR(2) Sof(O6)=Sof(H6A)=Sof(H6B)=FVAR(2) Fixed Sof: O8(0.5) H8A(0.5) H8B(0.5) 6.a Riding coordinates: O5(H5A,H5B), O6(H6A,H6B), O7(H7), O8(H8A,H8B), O9(H9), O6A(H6AA,H6AB) ; _shelx_res_file ; TITL 20220531al_a.res in P2/c 20220531al.res created by SHELXL-2019/2 at 11:07:20 on 08-Jun-2022 REM Old TITL 20220531aL in P2/c REM SHELXT solution in P2/c: R1 0.262, Rweak 0.013, Alpha 0.037 REM 1.331 for 254 systematic absences, Orientation as input REM Formula found by SHELXT: C17 N4 O3 K3A CELL 1.34139 12.0707 7.3415 18.2512 90 106.26 90 ZERR 2 0.0005 0.0003 0.0007 0 0.002 0 LATT 1 SYMM -X,+Y,0.5-Z SFAC C H K N O DISP C 0.0137 0.0067 57.1 DISP H 0 0 0.6 DISP K 0.3778 0.831 6349 DISP N 0.0241 0.0134 109.9 DISP O 0.0389 0.0241 193.4 UNIT 16 28 12 44 30 EQIV $1 2-X,+Y,0.5-Z EQIV $2 1-X,-Y,1-Z EQIV $3 1-X,1-Y,1-Z EQIV $4 1-X,1+Y,0.5-Z EQIV $5 +X,1-Y,-0.5+Z EQIV $6 2-X,1-Y,1-Z EQIV $7 2-X,2-Y,1-Z SADI 0.02 K2 O6A K2 O6 RIGU 0.001 0.002 K2 O6 RIGU 0.001 0.002 K2 O6A SIMU 0.01 0.02 2 O6A O6 L.S. 10 PLAN 2 SIZE 0.13 0.16 0.18 TEMP -123.15 CONF HTAB O5 N5_$5 HTAB O6 O5_$2 HTAB O6 O9 HTAB O7 N7_$6 HTAB O9 N3 HTAB O6A O1_$2 HTAB O6A O5_$2 HTAB O8 N9_$7 FREE K1 H6Aa_$2 FREE K2 K1_$2 FREE K2 C4_$3 FREE K2 H6Ab FREE K2 H6b FREE K3 H7_$1 FREE K3 K3_$1 FREE K3 K1 FREE K3 K2_$3 FREE K3 K2_$4 FREE K3 H6b_$3 FREE O8 O8_$1 FREE K3A H7_$1 FREE K3A O8_$1 FREE K3A K3A_$1 FREE K3A H8a FREE K3A H8b FREE K3A K2_$3 FREE K3A K2_$4 FREE C2 C1 BOND list 4 MORE -1 BOND $H fmap 2 acta OMIT 2 2 2 OMIT 3 1 3 REM REM REM WGHT 0.063900 2.785800 FVAR 0.47761 0.45457 0.88786 K1 3 0.702248 0.501016 0.409652 11.00000 0.02558 0.03828 = 0.02173 -0.00135 0.00556 -0.00327 K2 3 0.265217 -0.010688 0.547114 11.00000 0.02319 0.03272 = 0.03193 0.00352 0.00803 -0.00657 PART 1 K3 3 0.797985 0.881181 0.218039 21.00000 0.02997 0.02927 = 0.02104 -0.00631 -0.00285 0.00127 PART 2 K3A 3 0.844381 0.942774 0.221102 -21.00000 0.04887 0.08725 = 0.02052 0.01659 0.00975 0.03447 PART 0 O1 5 0.458623 0.193582 0.362842 11.00000 0.03933 0.06303 = 0.01848 -0.00577 0.00646 -0.01442 O2 5 0.325461 0.093446 0.412353 11.00000 0.02567 0.03931 = 0.02845 -0.00278 -0.00153 -0.01146 O3 5 0.903180 0.850485 0.370939 11.00000 0.03083 0.05115 = 0.01743 0.00396 0.00093 0.00074 O4 5 1.088583 0.896139 0.412969 11.00000 0.03122 0.04060 = 0.02461 0.00153 0.00972 -0.01096 O5 5 0.744312 0.458928 0.274295 11.00000 0.04029 0.11302 = 0.02720 0.00726 0.00461 0.00399 PART 2 AFIX 3 H5A 2 0.696162 0.471778 0.229165 11.00000 -1.50000 H5B 2 0.783852 0.361988 0.270555 11.00000 -1.50000 AFIX 0 PART 1 O6 5 0.315097 -0.088861 0.697964 31.00000 0.03337 0.08636 = 0.03459 0.01535 0.00435 0.00661 AFIX 3 H6A 2 0.319557 -0.199221 0.715934 31.00000 -1.50000 H6B 2 0.383577 -0.043441 0.717574 31.00000 -1.50000 AFIX 0 PART 0 O7 5 1.000000 0.658529 0.250000 10.50000 0.04353 0.03220 = 0.02163 0.00000 -0.00279 0.00000 AFIX 3 H7 2 1.037290 0.591319 0.286920 11.00000 -1.20000 AFIX 0 O8 5 0.951341 1.160589 0.249055 10.50000 0.08376 0.03351 = 0.01597 -0.00159 0.01097 -0.00858 AFIX 3 H8A 2 0.950441 1.211389 0.291965 10.50000 -1.50000 H8B 2 0.930001 1.246679 0.215295 10.50000 -1.50000 AFIX 0 N1 4 0.590309 0.306528 0.501235 11.00000 0.01950 0.03163 = 0.02052 -0.00124 0.00344 -0.00692 N2 4 0.445747 0.222320 0.551335 11.00000 0.02120 0.03314 = 0.01997 0.00180 0.00257 -0.00582 N3 4 0.532423 0.296193 0.609144 11.00000 0.02266 0.03479 = 0.02023 -0.00122 0.00405 -0.00914 N4 4 0.419217 0.170217 0.417338 11.00000 0.02412 0.03375 = 0.01966 -0.00074 0.00012 -0.00424 N5 4 0.717796 0.420580 0.621733 11.00000 0.02350 0.04838 = 0.01682 -0.00091 0.00505 -0.01181 N6 4 0.777468 0.492586 0.579777 11.00000 0.01925 0.03235 = 0.01712 -0.00120 0.00252 -0.00553 N7 4 0.877411 0.552585 0.620684 11.00000 0.01944 0.03972 = 0.01671 0.00081 0.00118 -0.01126 N8 4 0.896261 0.694547 0.502748 11.00000 0.01906 0.03129 = 0.01563 0.00020 0.00266 -0.00360 N9 4 1.051983 0.666646 0.606082 11.00000 0.02067 0.03178 = 0.01714 0.00373 0.00045 -0.00675 N10 4 1.089168 0.747399 0.549577 11.00000 0.02190 0.03087 = 0.01798 0.00281 0.00288 -0.00572 N11 4 0.995942 0.839467 0.420921 11.00000 0.02815 0.02680 = 0.01874 -0.00135 0.00525 -0.00274 C1 1 0.485620 0.234857 0.490828 11.00000 0.02314 0.02871 = 0.01777 0.00061 0.00279 -0.00365 C2 1 0.615818 0.344411 0.576583 11.00000 0.02165 0.03392 = 0.01626 0.00106 0.00459 -0.00719 C3 1 0.938823 0.636272 0.575580 11.00000 0.01999 0.02766 = 0.01454 -0.00138 0.00142 -0.00313 C4 1 0.994502 0.758625 0.491690 11.00000 0.02263 0.02438 = 0.01585 0.00014 0.00347 -0.00252 O9 5 0.500000 0.157159 0.750000 10.50000 0.10866 0.05261 = 0.04670 0.00000 0.04333 0.00000 AFIX 3 H9 2 0.508880 0.229709 0.714380 11.00000 -1.50000 AFIX 0 PART 2 O6A 5 0.348823 -0.168499 0.687065 -31.00000 0.04445 0.07833 = 0.04302 0.01686 0.01026 0.00161 AFIX 3 H6AA 2 0.334274 -0.270869 0.706535 -31.00000 -1.50000 H6AB 2 0.422264 -0.173219 0.690925 -31.00000 -1.50000 AFIX 0 HKLF 4 REM 20220531al_a.res in P2/c REM wR2 = 0.1401, GooF = S = 1.045, Restrained GooF = 1.044 for all data REM R1 = 0.0508 for 2506 Fo > 4sig(Fo) and 0.0681 for all 3165 data REM 256 parameters refined using 11 restraints END WGHT 0.0639 2.7855 REM Highest difference peak 0.618, deepest hole -0.591, 1-sigma level 0.091 Q1 1 0.3566 0.1860 0.7310 11.00000 0.05 0.62 Q2 1 0.8024 0.2993 0.2474 11.00000 0.05 0.60 ; _shelx_res_checksum 1075 _olex2_submission_special_instructions 'No special instructions were received' loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y, -z+1/2' '-x, -y, -z' 'x, -y, 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 K1 K 0.70225(6) 0.50102(10) 0.40965(4) 0.0288(2) Uani 1 1 d . . . . . K2 K 0.26522(6) -0.01069(10) 0.54711(4) 0.0292(2) Uani 1 1 d D . . . . K3 K 0.7980(6) 0.8812(5) 0.21804(16) 0.0288(11) Uani 0.455(16) 1 d . . P A 1 K3A K 0.8444(7) 0.9428(13) 0.22110(19) 0.052(2) Uani 0.545(16) 1 d . . P A 2 O1 O 0.4586(2) 0.1936(4) 0.36284(14) 0.0406(7) Uani 1 1 d . . . . . O2 O 0.3255(2) 0.0934(3) 0.41235(14) 0.0330(6) Uani 1 1 d . . . . . O3 O 0.9032(2) 0.8505(4) 0.37094(13) 0.0343(6) Uani 1 1 d . . . . . O4 O 1.0886(2) 0.8961(3) 0.41297(14) 0.0318(6) Uani 1 1 d . . . . . O5 O 0.7443(3) 0.4589(6) 0.27429(17) 0.0612(10) Uani 1 1 d . . . . . H5A H 0.696162 0.471778 0.229165 0.092 Uiso 1 1 d R U . A 2 H5B H 0.783852 0.361988 0.270555 0.092 Uiso 1 1 d R U . A 2 O6 O 0.3151(4) -0.0889(10) 0.6980(2) 0.0525(16) Uani 0.888(17) 1 d D U P B 1 H6A H 0.319557 -0.199221 0.715934 0.079 Uiso 0.888(17) 1 d R U P B 1 H6B H 0.383577 -0.043441 0.717574 0.079 Uiso 0.888(17) 1 d R U P B 1 O7 O 1.000000 0.6585(5) 0.250000 0.0349(8) Uani 1 2 d S T P . . H7 H 1.037290 0.591319 0.286920 0.042 Uiso 1 1 d R U . A . O8 O 0.9513(5) 1.1606(7) 0.2491(3) 0.0450(16) Uani 0.5 1 d . . P . . H8A H 0.950441 1.211389 0.291965 0.068 Uiso 0.5 1 d R U P A . H8B H 0.930001 1.246679 0.215295 0.068 Uiso 0.5 1 d R U P . . N1 N 0.5903(2) 0.3065(4) 0.50124(15) 0.0243(6) Uani 1 1 d . . . . . N2 N 0.4457(2) 0.2223(4) 0.55133(15) 0.0254(6) Uani 1 1 d . . . . . N3 N 0.5324(2) 0.2962(4) 0.60914(16) 0.0263(6) Uani 1 1 d . . . . . N4 N 0.4192(2) 0.1702(4) 0.41734(16) 0.0271(6) Uani 1 1 d . . . . . N5 N 0.7178(3) 0.4206(4) 0.62173(16) 0.0297(7) Uani 1 1 d . . . . . N6 N 0.7775(2) 0.4926(4) 0.57978(15) 0.0234(6) Uani 1 1 d . . . . . N7 N 0.8774(2) 0.5526(4) 0.62068(15) 0.0261(6) Uani 1 1 d . . . . . N8 N 0.8963(2) 0.6945(4) 0.50275(15) 0.0224(6) Uani 1 1 d . . . . . N9 N 1.0520(2) 0.6666(4) 0.60608(15) 0.0242(6) Uani 1 1 d . . . . . N10 N 1.0892(2) 0.7474(4) 0.54958(15) 0.0241(6) Uani 1 1 d . . . . . N11 N 0.9959(2) 0.8395(4) 0.42092(15) 0.0248(6) Uani 1 1 d . . . . . C1 C 0.4856(3) 0.2349(5) 0.49083(18) 0.0238(7) Uani 1 1 d . . . . . C2 C 0.6158(3) 0.3444(5) 0.57658(18) 0.0241(7) Uani 1 1 d . . . . . C3 C 0.9388(3) 0.6363(4) 0.57558(18) 0.0214(7) Uani 1 1 d . . . . . C4 C 0.9945(3) 0.7586(4) 0.49169(17) 0.0213(7) Uani 1 1 d . . . . . O9 O 0.500000 0.1572(7) 0.750000 0.0650(14) Uani 1 2 d S T P . . H9 H 0.508880 0.229709 0.714380 0.097 Uiso 1 1 d R U . . . O6A O 0.349(4) -0.168(7) 0.6871(17) 0.056(5) Uani 0.112(17) 1 d D U P B 2 H6AA H 0.334274 -0.270869 0.706535 0.084 Uiso 0.112(17) 1 d R U P B 2 H6AB H 0.422264 -0.173219 0.690925 0.084 Uiso 0.112(17) 1 d R U P B 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 K1 0.0256(4) 0.0383(4) 0.0217(4) -0.0014(3) 0.0056(3) -0.0033(3) K2 0.0232(4) 0.0327(4) 0.0319(4) 0.0035(3) 0.0080(3) -0.0066(3) K3 0.030(2) 0.0293(14) 0.0210(10) -0.0063(8) -0.0028(10) 0.0013(12) K3A 0.049(3) 0.087(4) 0.0205(10) 0.0166(14) 0.0097(13) 0.034(3) O1 0.0393(16) 0.0630(18) 0.0185(13) -0.0058(12) 0.0065(12) -0.0144(14) O2 0.0257(13) 0.0393(15) 0.0284(13) -0.0028(11) -0.0015(11) -0.0115(11) O3 0.0308(14) 0.0511(16) 0.0174(12) 0.0040(11) 0.0009(11) 0.0007(12) O4 0.0312(14) 0.0406(15) 0.0246(13) 0.0015(11) 0.0097(11) -0.0110(11) O5 0.0403(18) 0.113(3) 0.0272(15) 0.0073(17) 0.0046(14) 0.0040(18) O6 0.033(2) 0.086(4) 0.0346(18) 0.0153(18) 0.0044(14) 0.007(2) O7 0.044(2) 0.0322(19) 0.0216(18) 0.000 -0.0028(16) 0.000 O8 0.084(5) 0.034(3) 0.016(2) -0.002(2) 0.011(4) -0.009(3) N1 0.0195(14) 0.0316(15) 0.0205(14) -0.0012(12) 0.0034(12) -0.0069(11) N2 0.0212(14) 0.0331(16) 0.0200(14) 0.0018(12) 0.0026(12) -0.0058(12) N3 0.0227(14) 0.0348(15) 0.0202(14) -0.0012(12) 0.0041(12) -0.0091(12) N4 0.0241(15) 0.0337(16) 0.0197(15) -0.0007(12) 0.0001(12) -0.0042(12) N5 0.0235(15) 0.0484(19) 0.0168(14) -0.0009(13) 0.0051(12) -0.0118(13) N6 0.0193(14) 0.0324(15) 0.0171(14) -0.0012(11) 0.0025(12) -0.0055(11) N7 0.0194(14) 0.0397(16) 0.0167(14) 0.0008(12) 0.0012(12) -0.0113(12) N8 0.0191(14) 0.0313(15) 0.0156(13) 0.0002(11) 0.0027(11) -0.0036(11) N9 0.0207(14) 0.0318(15) 0.0171(14) 0.0037(11) 0.0004(12) -0.0067(11) N10 0.0219(14) 0.0309(15) 0.0180(14) 0.0028(11) 0.0029(12) -0.0057(11) N11 0.0282(16) 0.0268(15) 0.0187(14) -0.0013(11) 0.0053(13) -0.0027(12) C1 0.0231(17) 0.0287(18) 0.0178(16) 0.0006(13) 0.0028(14) -0.0036(13) C2 0.0216(17) 0.0339(18) 0.0163(16) 0.0011(13) 0.0046(14) -0.0072(14) C3 0.0200(16) 0.0277(16) 0.0145(15) -0.0014(13) 0.0014(13) -0.0031(13) C4 0.0226(16) 0.0244(16) 0.0158(15) 0.0001(12) 0.0035(13) -0.0025(13) O9 0.109(4) 0.053(3) 0.047(3) 0.000 0.043(3) 0.000 O6A 0.044(10) 0.078(10) 0.043(7) 0.017(7) 0.010(6) 0.002(8) 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' K K 0.3778 0.8310 '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 K2 K1 K2 156.10(3) 3_656 3_666 ? K2 K1 H6AA 62.1(6) 3_656 3_656 ? K2 K1 H6AA 140.7(6) 3_666 3_656 ? O5 K1 K2 92.78(9) . 3_656 ? O5 K1 K2 105.58(9) . 3_666 ? O5 K1 N1 137.43(11) . . ? O5 K1 N2 126.33(10) . 3_666 ? O5 K1 N3 110.69(9) . 3_666 ? O5 K1 N6 151.39(9) . . ? O5 K1 N8 105.71(9) . . ? O5 K1 N9 57.90(9) . 3_766 ? O5 K1 N10 78.33(9) . 3_766 ? O5 K1 O6A 54.5(6) . 3_656 ? O5 K1 H6AA 38.7(7) . 3_656 ? N1 K1 K2 54.34(6) . 3_656 ? N1 K1 K2 114.38(6) . 3_666 ? N1 K1 N2 77.29(8) . 3_666 ? N1 K1 N3 74.72(8) . 3_666 ? N1 K1 N6 55.11(8) . . ? N1 K1 N8 110.42(8) . . ? N1 K1 N9 117.10(8) . 3_766 ? N1 K1 N10 93.03(8) . 3_766 ? N1 K1 O6A 83.2(7) . 3_656 ? N1 K1 H6AA 98.7(7) . 3_656 ? N2 K1 K2 131.54(6) 3_666 3_656 ? N2 K1 K2 45.85(6) 3_666 3_666 ? N2 K1 N3 25.90(7) 3_666 3_666 ? N2 K1 N6 77.84(8) 3_666 . ? N2 K1 N9 155.10(8) 3_666 3_766 ? N2 K1 N10 151.87(8) 3_666 3_766 ? N2 K1 O6A 132.5(10) 3_666 3_656 ? N2 K1 H6AA 131.5(10) 3_666 3_656 ? N3 K1 K2 121.80(6) 3_666 3_656 ? N3 K1 K2 66.10(5) 3_666 3_666 ? N3 K1 N9 167.35(7) 3_666 3_766 ? N3 K1 H6AA 105.8(11) 3_666 3_656 ? N6 K1 K2 76.91(6) . 3_656 ? N6 K1 K2 79.72(6) . 3_666 ? N6 K1 N3 97.25(8) . 3_666 ? N6 K1 N9 93.66(7) . 3_766 ? N6 K1 N10 75.04(8) . 3_766 ? N6 K1 H6AA 138.9(6) . 3_656 ? N8 K1 K2 50.99(6) . 3_666 ? N8 K1 K2 109.77(6) . 3_656 ? N8 K1 N2 87.97(8) . 3_666 ? N8 K1 N3 113.22(8) . 3_666 ? N8 K1 N6 55.33(7) . . ? N8 K1 N9 68.27(7) . 3_766 ? N8 K1 N10 70.53(8) . 3_766 ? N8 K1 O6A 139.5(10) . 3_656 ? N8 K1 H6AA 135.9(11) . 3_656 ? N9 K1 K2 67.00(5) 3_766 3_656 ? N9 K1 K2 109.91(5) 3_766 3_666 ? N9 K1 H6AA 69.2(11) 3_766 3_656 ? N10 K1 K2 120.57(6) 3_766 3_666 ? N10 K1 K2 47.72(5) 3_766 3_656 ? N10 K1 N3 167.75(8) 3_766 3_666 ? N10 K1 N9 24.53(7) 3_766 3_766 ? N10 K1 H6AA 75.7(10) 3_766 3_656 ? O6A K1 N6 123.6(4) 3_656 . ? K1 K2 K3 69.14(6) 3_666 3_666 ? K1 K2 K3A 105.56(12) 3_666 2_645 ? K1 K2 H6B 82.8 3_666 . ? K1 K2 H6AB 101.8 3_666 . ? K3 K2 K3A 154.19(19) 3_666 2_645 ? K3 K2 H6B 39.4 3_666 . ? K3A K2 H6AB 143.1 2_645 . ? O2 K2 K1 83.08(5) . 3_666 ? O2 K2 K3 152.17(9) . 3_666 ? O2 K2 K3A 35.93(6) . 2_645 ? O2 K2 O3 132.73(8) . 3_666 ? O2 K2 H6B 137.8 . . ? O2 K2 N1 68.86(8) . 3_656 ? O2 K2 N8 80.35(7) . 3_666 ? O2 K2 H6AB 127.2 . . ? O3 K2 K1 64.45(5) 3_666 3_666 ? O3 K2 K3 34.24(8) 3_666 3_666 ? O3 K2 K3A 120.10(15) 3_666 2_645 ? O3 K2 H6B 73.6 3_666 . ? O3 K2 H6AB 93.9 3_666 . ? O4 K2 K1 114.98(6) 1_445 3_666 ? O4 K2 K3 124.40(10) 1_445 3_666 ? O4 K2 K3A 33.21(7) 1_445 2_645 ? O4 K2 O2 68.49(7) 1_445 . ? O4 K2 O3 94.15(7) 1_445 3_666 ? O4 K2 H6B 152.1 1_445 . ? O4 K2 N1 86.08(8) 1_445 3_656 ? O4 K2 N8 70.03(8) 1_445 3_666 ? O4 K2 H6AB 142.2 1_445 . ? O6 K2 K1 90.96(16) . 3_666 ? O6 K2 K3 32.35(17) . 3_666 ? O6 K2 K3A 163.33(18) . 2_645 ? O6 K2 O2 153.32(11) . . ? O6 K2 O3 64.91(16) . 3_666 ? O6 K2 O4 136.35(10) . 1_445 ? O6 K2 H6B 16.0 . . ? O6 K2 N1 99.20(18) . 3_656 ? O6 K2 N2 98.87(11) . . ? O6 K2 N8 114.34(18) . 3_666 ? O6 K2 N10 78.56(11) . 1_445 ? N1 K2 K1 135.99(6) 3_656 3_666 ? N1 K2 K3 131.49(6) 3_656 3_666 ? N1 K2 K3A 70.52(16) 3_656 2_645 ? N1 K2 O3 156.60(8) 3_656 3_666 ? N1 K2 H6B 95.5 3_656 . ? N1 K2 H6AB 72.6 3_656 . ? N2 K2 K1 49.56(6) . 3_666 ? N2 K2 K3 100.35(11) . 3_666 ? N2 K2 K3A 93.66(7) . 2_645 ? N2 K2 O2 57.85(7) . . ? N2 K2 O3 111.99(8) . 3_666 ? N2 K2 O4 124.76(8) . 1_445 ? N2 K2 H6B 83.1 . . ? N2 K2 N1 86.49(8) . 3_656 ? N2 K2 N8 88.27(8) . 3_666 ? N2 K2 N10 177.24(9) . 1_445 ? N2 K2 H6AB 85.5 . . ? N8 K2 K1 47.65(5) 3_666 3_666 ? N8 K2 K3 82.04(6) 3_666 3_666 ? N8 K2 K3A 76.80(16) 3_666 2_645 ? N8 K2 O3 52.44(7) 3_666 3_666 ? N8 K2 H6B 116.7 3_666 . ? N8 K2 N1 146.46(8) 3_666 3_656 ? N8 K2 H6AB 139.9 3_666 . ? N10 K2 K1 131.08(6) 1_445 3_666 ? N10 K2 K3 78.03(10) 1_445 3_666 ? N10 K2 K3A 88.68(6) 1_445 2_645 ? N10 K2 O2 124.40(8) 1_445 . ? N10 K2 O3 67.91(8) 1_445 3_666 ? N10 K2 O4 57.85(7) 1_445 1_445 ? N10 K2 H6B 94.3 1_445 . ? N10 K2 N1 92.93(8) 1_445 3_656 ? N10 K2 N8 93.69(8) 1_445 3_666 ? N10 K2 H6AB 91.7 1_445 . ? O6A K2 O2 143.4(12) . . ? O6A K2 N2 98.9(8) . . ? O6A K2 H6AB 16.4 . . ? O2 K3 O4 65.07(12) 2_665 2_755 ? O2 K3 O5 130.3(2) 2_665 . ? O2 K3 H6B 81.02(14) 2_665 3_666 ? O2 K3 H7 124.38(17) 2_665 2_755 ? O2 K3 C2 63.40(10) 2_665 4_565 ? O3 K3 O2 150.67(12) . 2_665 ? O3 K3 O4 128.1(3) . 2_755 ? O3 K3 O5 71.84(13) . . ? O3 K3 O6 68.97(13) . 3_666 ? O3 K3 H6B 79.32(15) . 3_666 ? O3 K3 O7 67.56(10) . . ? O3 K3 H7 81.16(10) . 2_755 ? O3 K3 N5 123.44(16) . 4_565 ? O3 K3 C2 140.2(2) . 4_565 ? O4 K3 O5 115.70(10) 2_755 . ? O4 K3 H6B 145.32(13) 2_755 3_666 ? O4 K3 H7 63.12(13) 2_755 2_755 ? O4 K3 C2 75.85(9) 2_755 4_565 ? O5 K3 H6B 91.3(2) . 3_666 ? O5 K3 H7 62.19(9) . 2_755 ? O6 K3 O2 86.48(14) 3_666 2_665 ? O6 K3 O4 143.63(19) 3_666 2_755 ? O6 K3 O5 99.8(2) 3_666 . ? O6 K3 H6B 16.69(6) 3_666 3_666 ? O6 K3 O7 136.46(12) 3_666 . ? O6 K3 H7 149.13(15) 3_666 2_755 ? O6 K3 N5 129.7(3) 3_666 4_565 ? O6 K3 C2 112.4(2) 3_666 4_565 ? O7 K3 O2 133.8(2) . 2_665 ? O7 K3 O4 68.80(15) . 2_755 ? O7 K3 O5 68.84(10) . . ? O7 K3 H6B 145.14(16) . 3_666 ? O7 K3 H7 16.92(3) . 2_755 ? O7 K3 C2 102.39(10) . 4_565 ? H7 K3 H6B 151.0 2_755 3_666 ? O8 K3 O2 85.89(19) . 2_665 ? O8 K3 O3 75.79(17) . . ? O8 K3 O4 73.1(2) . 2_755 ? O8 K3 O5 143.72(18) . . ? O8 K3 O6 83.22(17) . 3_666 ? O8 K3 H6B 98.52(17) . 3_666 ? O8 K3 O7 84.1(2) . . ? O8 K3 H7 97.2(3) . 2_755 ? O8 K3 N5 144.8(3) . 4_565 ? O8 K3 C2 143.3(2) . 4_565 ? N5 K3 O2 84.41(11) 4_565 2_665 ? N5 K3 O4 72.15(11) 4_565 2_755 ? N5 K3 O5 53.79(12) 4_565 . ? N5 K3 H6B 113.2(3) 4_565 3_666 ? N5 K3 O7 78.61(10) 4_565 . ? N5 K3 H7 61.88(8) 4_565 2_755 ? N5 K3 C2 24.47(9) 4_565 4_565 ? C2 K3 O5 68.80(13) 4_565 . ? C2 K3 H6B 96.0(2) 4_565 3_666 ? C2 K3 H7 85.48(8) 4_565 2_755 ? O2 K3A H7 121.4(2) 2_665 2_755 ? O2 K3A H8A 105.7 2_665 . ? O2 K3A H8B 80.0 2_665 . ? O2 K3A N5 75.1(2) 2_665 4_565 ? O3 K3A O2 149.13(19) . 2_665 ? O3 K3A O4 142.30(12) . 2_755 ? O3 K3A O7 69.28(8) . . ? O3 K3A H7 80.74(12) . 2_755 ? O3 K3A H8A 74.0 . . ? O3 K3A H8B 105.9 . . ? O3 K3A N5 107.4(3) . 4_565 ? O4 K3A O2 68.04(9) 2_755 2_665 ? O4 K3A H7 65.87(9) 2_755 2_755 ? O4 K3A H8A 108.4 2_755 . ? O4 K3A H8B 81.2 2_755 . ? O4 K3A N5 68.24(19) 2_755 4_565 ? O7 K3A O2 136.6(2) . 2_665 ? O7 K3A O4 74.16(8) . 2_755 ? O7 K3A H7 16.61(4) . 2_755 ? O7 K3A H8A 105.9 . . ? O7 K3A H8B 114.9 . . ? O7 K3A N5 71.6(2) . 4_565 ? O8 K3A O2 99.2(3) . 2_665 ? O8 K3A O3 88.6(3) . . ? O8 K3A O4 89.8(3) . 2_755 ? O8 K3A O7 101.4(3) . . ? O8 K3A H7 114.6(3) . 2_755 ? O8 K3A H8A 18.6 . . ? O8 K3A H8B 19.2 . . ? O8 K3A N5 158.0(2) . 4_565 ? H8A K3A H7 121.7 . 2_755 ? H8A K3A H8B 32.1 . . ? H8B K3A H7 124.6 . 2_755 ? N5 K3A H7 55.52(18) 4_565 2_755 ? N5 K3A H8A 176.2 4_565 . ? N5 K3A H8B 146.0 4_565 . ? K2 O2 K3 111.61(13) . 2_645 ? K2 O2 K3A 109.12(9) . 2_645 ? K3 O2 K3A 14.01(10) 2_645 2_645 ? N4 O2 K2 120.2(2) . . ? N4 O2 K3 123.6(2) . 2_645 ? N4 O2 K3A 130.0(2) . 2_645 ? K3 O3 K2 106.49(15) . 3_666 ? N11 O3 K2 104.61(18) . 3_666 ? N11 O3 K3 145.8(3) . . ? N11 O3 K3A 133.6(3) . . ? K2 O4 K3 106.78(11) 1_665 2_755 ? N11 O4 K2 117.62(19) . 1_665 ? N11 O4 K3 133.8(2) . 2_755 ? N11 O4 K3A 129.3(2) . 2_755 ? K1 O5 K3 106.04(14) . . ? K1 O5 H5A 127.8 . . ? K1 O5 H5B 114.6 . . ? H5A O5 H5B 104.5 . . ? K2 O6 K3 116.2(2) . 3_666 ? K2 O6 H6A 123.6 . . ? K2 O6 H6B 104.6 . . ? K3 O6 H6A 106.9 3_666 . ? K3 O6 H6B 96.9 3_666 . ? H6A O6 H6B 104.5 . . ? K3 O7 K3 110.2(3) 2_755 . ? K3 O7 H7 136.3 . . ? K3 O7 H7 136.25(11) 2_755 2_755 ? K3 O7 H7 86.5 2_755 . ? K3 O7 H7 86.47(8) . 2_755 ? K3A O7 K3A 81.7(5) 2_755 . ? K3A O7 H7 96.1 2_755 . ? K3A O7 H7 140.2 . . ? H7 O7 H7 109.5 . 2_755 ? K3 O8 K3A 96.80(17) . 2_755 ? K3 O8 H8A 109.4 . . ? K3 O8 H8B 110.6 . . ? K3A O8 H8A 107.2 2_755 . ? K3A O8 H8A 113.4 . . ? K3A O8 H8B 127.6 2_755 . ? K3A O8 H8B 110.7 . . ? H8A O8 H8B 104.5 . . ? K1 N1 K2 77.42(7) . 3_656 ? C1 N1 K1 135.2(2) . . ? C1 N1 K2 105.8(2) . 3_656 ? C1 N1 C2 99.4(3) . . ? C2 N1 K1 119.3(2) . . ? C2 N1 K2 116.9(2) . 3_656 ? K2 N2 K1 84.59(8) . 3_666 ? N3 N2 K1 85.67(18) . 3_666 ? N3 N2 K2 133.93(19) . . ? C1 N2 K1 123.0(2) . 3_666 ? C1 N2 K2 119.3(2) . . ? C1 N2 N3 103.7(3) . . ? N2 N3 K1 68.43(17) . 3_666 ? C2 N3 K1 126.1(2) . 3_666 ? C2 N3 N2 105.5(3) . . ? O1 N4 O2 123.7(3) . . ? O1 N4 C1 117.9(3) . . ? O2 N4 C1 118.4(3) . . ? K3 N5 K3A 9.02(9) 4_566 4_566 ? N6 N5 K3 122.3(3) . 4_566 ? N6 N5 K3A 113.5(2) . 4_566 ? N6 N5 C2 111.0(3) . . ? C2 N5 K3 98.4(2) . 4_566 ? C2 N5 K3A 101.2(2) . 4_566 ? N5 N6 K1 124.3(2) . . ? N5 N6 N7 112.1(3) . . ? N7 N6 K1 123.51(19) . . ? N6 N7 C3 111.7(3) . . ? K1 N8 K2 81.36(7) . 3_666 ? C3 N8 K1 116.7(2) . . ? C3 N8 K2 125.3(2) . 3_666 ? C4 N8 K1 134.1(2) . . ? C4 N8 K2 102.1(2) . 3_666 ? C4 N8 C3 98.6(3) . . ? N10 N9 K1 66.64(16) . 3_766 ? C3 N9 K1 137.6(2) . 3_766 ? C3 N9 N10 105.7(3) . . ? K2 N10 K1 78.58(7) 1_665 3_766 ? N9 N10 K1 88.83(18) . 3_766 ? N9 N10 K2 134.59(19) . 1_665 ? C4 N10 K1 134.9(2) . 3_766 ? C4 N10 K2 116.1(2) . 1_665 ? C4 N10 N9 103.7(2) . . ? O3 N11 O4 123.6(3) . . ? O3 N11 C4 117.3(3) . . ? O4 N11 C4 119.1(3) . . ? N1 C1 N4 121.5(3) . . ? N2 C1 N1 117.4(3) . . ? N2 C1 N4 121.1(3) . . ? N1 C2 K3 126.9(3) . 4_566 ? N1 C2 N3 114.1(3) . . ? N1 C2 N5 126.6(3) . . ? N3 C2 K3 86.6(2) . 4_566 ? N3 C2 N5 119.3(3) . . ? N5 C2 K3 57.17(19) . 4_566 ? N8 C3 N7 126.9(3) . . ? N9 C3 N7 118.4(3) . . ? N9 C3 N8 114.7(3) . . ? N8 C4 K2 56.13(17) . 3_666 ? N8 C4 N11 121.2(3) . . ? N10 C4 K2 135.3(2) . 3_666 ? N10 C4 N8 117.4(3) . . ? N10 C4 N11 121.5(3) . . ? N11 C4 K2 80.55(18) . 3_666 ? H9 O9 H9 104.5 . 2_656 ? K1 O6A H6AA 60.1 3_656 . ? K1 O6A H6AB 93.0 3_656 . ? K2 O6A K1 80.3(10) . 3_656 ? K2 O6A H6AA 133.3 . . ? K2 O6A H6AB 101.2 . . ? H6AA O6A H6AB 104.5 . . ? 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 K1 K2 3.8215(11) 3_666 ? K1 K2 3.6826(11) 3_656 ? K1 O5 2.676(3) . ? K1 N1 2.815(3) . ? K1 N2 2.922(3) 3_666 ? K1 N3 3.133(3) 3_666 ? K1 N6 2.982(3) . ? K1 N8 2.857(3) . ? K1 N9 3.298(3) 3_766 ? K1 N10 3.028(3) 3_766 ? K1 O6A 2.97(5) 3_656 ? K1 H6AA 2.65(5) 3_656 ? K2 K3 4.657(5) 3_666 ? K2 K3A 4.712(3) 2_645 ? K2 O2 2.857(3) . ? K2 O3 3.075(3) 3_666 ? K2 O4 2.843(3) 1_445 ? K2 O6 2.710(3) . ? K2 H6B 3.0478 . ? K2 N1 3.066(3) 3_656 ? K2 N2 2.754(3) . ? K2 N8 3.003(3) 3_666 ? K2 N10 2.779(3) 1_445 ? K2 O6A 2.728(17) . ? K2 H6AB 3.0200 . ? K3 O2 2.886(4) 2_665 ? K3 O3 2.732(3) . ? K3 O4 3.072(7) 2_755 ? K3 O5 3.385(7) . ? K3 O6 2.777(9) 3_666 ? K3 H6B 3.008(9) 3_666 ? K3 O7 2.857(5) . ? K3 H7 2.931(5) 2_755 ? K3 O8 2.714(9) . ? K3 N5 2.825(5) 4_565 ? K3 C2 3.326(5) 4_565 ? K3A O2 2.926(4) 2_665 ? K3A O3 2.712(3) . ? K3A O4 2.805(3) 2_755 ? K3A O7 2.758(4) . ? K3A H7 2.973(6) 2_755 ? K3A O8 2.029(14) . ? K3A H8A 2.5047 . ? K3A H8B 2.4736 . ? K3A N5 3.345(12) 4_565 ? O1 N4 1.229(4) . ? O2 N4 1.245(4) . ? O3 N11 1.233(4) . ? O4 N11 1.239(4) . ? O5 H5A 0.8701 . ? O5 H5B 0.8702 . ? O6 H6A 0.8701 . ? O6 H6B 0.8700 . ? O7 H7 0.8546 . ? O7 H7 0.8546 2_755 ? O8 H8A 0.8702 . ? O8 H8B 0.8698 . ? N1 C1 1.332(4) . ? N1 C2 1.351(4) . ? N2 N3 1.373(4) . ? N2 C1 1.326(4) . ? N3 C2 1.352(4) . ? N4 C1 1.437(4) . ? N5 N6 1.301(4) . ? N5 C2 1.392(4) . ? N6 N7 1.305(4) . ? N7 C3 1.395(4) . ? N8 C3 1.353(4) . ? N8 C4 1.342(4) . ? N9 N10 1.370(4) . ? N9 C3 1.341(4) . ? N10 C4 1.324(4) . ? N11 C4 1.426(4) . ? O9 H9 0.8700 . ? O9 H9 0.8700 2_656 ? O6A H6AA 0.8700 . ? O6A H6AB 0.8701 . ? 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_site_symmetry_A _geom_hbond_publ_flag O5 H5A N5 0.87 2.20 2.853(4) 132.0 4_565 yes O6 H6A O5 0.87 2.08 2.891(7) 154.1 3_656 yes O6 H6B O9 0.87 2.01 2.821(6) 155.3 . yes O7 H7 N7 0.85 2.01 2.865(3) 175.6 3_766 yes O8 H8A N9 0.87 2.07 2.943(6) 179.8 3_776 yes O9 H9 N3 0.87 2.08 2.893(3) 155.8 . yes O6A H6AA O5 0.87 1.76 2.60(3) 159.7 3_656 yes O6A H6AB O1 0.87 1.96 2.73(6) 146.7 3_656 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 _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag K1 N1 C1 N2 -151.6(2) . . . . ? K1 N1 C1 N4 29.6(5) . . . . ? K1 N1 C2 K3 -98.0(3) . . . 4_566 ? K1 N1 C2 N3 157.3(2) . . . . ? K1 N1 C2 N5 -24.6(5) . . . . ? K1 N2 N3 C2 -123.2(2) 3_666 . . . ? K1 N2 C1 N1 94.7(3) 3_666 . . . ? K1 N2 C1 N4 -86.5(3) 3_666 . . . ? K1 N3 C2 K3 156.19(18) 3_666 . . 4_566 ? K1 N3 C2 N1 -74.6(4) 3_666 . . . ? K1 N3 C2 N5 107.2(3) 3_666 . . . ? K1 N6 N7 C3 5.8(4) . . . . ? K1 N8 C3 N7 -29.7(4) . . . . ? K1 N8 C3 N9 151.3(2) . . . . ? K1 N8 C4 K2 89.6(2) . . . 3_666 ? K1 N8 C4 N10 -142.3(3) . . . . ? K1 N8 C4 N11 39.2(5) . . . . ? K1 N9 N10 K2 -72.6(2) 3_766 . . 1_665 ? K1 N9 N10 C4 136.2(2) 3_766 . . . ? K1 N9 C3 N7 107.2(3) 3_766 . . . ? K1 N9 C3 N8 -73.7(4) 3_766 . . . ? K1 N10 C4 K2 170.85(11) 3_766 . . 3_666 ? K1 N10 C4 N8 102.5(3) 3_766 . . . ? K1 N10 C4 N11 -79.0(4) 3_766 . . . ? K2 O2 N4 O1 168.4(3) . . . . ? K2 O2 N4 C1 -11.4(4) . . . . ? K2 O3 N11 O4 -131.1(3) 3_666 . . . ? K2 O3 N11 C4 48.1(3) 3_666 . . . ? K2 O4 N11 O3 155.5(2) 1_665 . . . ? K2 O4 N11 C4 -23.7(4) 1_665 . . . ? K2 N1 C1 N2 120.5(3) 3_656 . . . ? K2 N1 C1 N4 -58.3(3) 3_656 . . . ? K2 N1 C2 K3 -7.7(3) 3_656 . . 4_566 ? K2 N1 C2 N3 -112.4(3) 3_656 . . . ? K2 N1 C2 N5 65.6(4) 3_656 . . . ? K2 N2 N3 K1 -78.2(2) . . . 3_666 ? K2 N2 N3 C2 158.6(2) . . . . ? K2 N2 C1 N1 -161.8(2) . . . . ? K2 N2 C1 N4 17.0(4) . . . . ? K2 N8 C3 N7 68.9(4) 3_666 . . . ? K2 N8 C3 N9 -110.1(3) 3_666 . . . ? K2 N8 C4 N10 128.1(3) 3_666 . . . ? K2 N8 C4 N11 -50.4(3) 3_666 . . . ? K2 N10 C4 K2 -88.9(3) 1_665 . . 3_666 ? K2 N10 C4 N8 -157.3(2) 1_665 . . . ? K2 N10 C4 N11 21.2(4) 1_665 . . . ? K3 O2 N4 O1 14.3(5) 2_645 . . . ? K3 O2 N4 C1 -165.5(2) 2_645 . . . ? K3 O3 N11 O4 23.7(6) . . . . ? K3 O3 N11 C4 -157.1(3) . . . . ? K3 O4 N11 O3 -42.0(5) 2_755 . . . ? K3 O4 N11 C4 138.8(3) 2_755 . . . ? K3 N5 N6 K1 116.7(2) 4_566 . . . ? K3 N5 N6 N7 -59.9(3) 4_566 . . . ? K3 N5 C2 N1 -114.2(4) 4_566 . . . ? K3 N5 C2 N3 63.7(4) 4_566 . . . ? K3A O2 N4 O1 -1.3(6) 2_645 . . . ? K3A O2 N4 C1 178.9(4) 2_645 . . . ? K3A O3 N11 O4 10.2(6) . . . . ? K3A O3 N11 C4 -170.6(3) . . . . ? K3A O4 N11 O3 -25.8(6) 2_755 . . . ? K3A O4 N11 C4 155.0(4) 2_755 . . . ? K3A N5 N6 K1 114.66(18) 4_566 . . . ? K3A N5 N6 N7 -61.9(3) 4_566 . . . ? K3A N5 C2 N1 -105.5(4) 4_566 . . . ? K3A N5 C2 N3 72.4(3) 4_566 . . . ? O1 N4 C1 N1 -4.6(5) . . . . ? O1 N4 C1 N2 176.6(3) . . . . ? O2 N4 C1 N1 175.2(3) . . . . ? O2 N4 C1 N2 -3.6(5) . . . . ? O3 N11 C4 K2 -39.4(3) . . . 3_666 ? O3 N11 C4 N8 1.1(5) . . . . ? O3 N11 C4 N10 -177.4(3) . . . . ? O4 N11 C4 K2 139.9(3) . . . 3_666 ? O4 N11 C4 N8 -179.7(3) . . . . ? O4 N11 C4 N10 1.9(5) . . . . ? N2 N3 C2 K3 -129.5(2) . . . 4_566 ? N2 N3 C2 N1 -0.3(4) . . . . ? N2 N3 C2 N5 -178.5(3) . . . . ? N3 N2 C1 N1 0.9(4) . . . . ? N3 N2 C1 N4 179.7(3) . . . . ? N5 N6 N7 C3 -177.5(3) . . . . ? N6 N5 C2 K3 129.5(3) . . . 4_566 ? N6 N5 C2 N1 15.2(5) . . . . ? N6 N5 C2 N3 -166.8(3) . . . . ? N6 N7 C3 N8 16.2(5) . . . . ? N6 N7 C3 N9 -164.8(3) . . . . ? N9 N10 C4 K2 68.6(3) . . . 3_666 ? N9 N10 C4 N8 0.2(4) . . . . ? N9 N10 C4 N11 178.8(3) . . . . ? N10 N9 C3 N7 179.5(3) . . . . ? N10 N9 C3 N8 -1.4(4) . . . . ? C1 N1 C2 K3 105.5(3) . . . 4_566 ? C1 N1 C2 N3 0.8(4) . . . . ? C1 N1 C2 N5 178.8(4) . . . . ? C1 N2 N3 K1 122.9(2) . . . 3_666 ? C1 N2 N3 C2 -0.3(4) . . . . ? C2 N1 C1 N2 -1.1(4) . . . . ? C2 N1 C1 N4 -179.9(3) . . . . ? C2 N5 N6 K1 1.4(4) . . . . ? C2 N5 N6 N7 -175.1(3) . . . . ? C3 N8 C4 K2 -129.0(2) . . . 3_666 ? C3 N8 C4 N10 -1.0(4) . . . . ? C3 N8 C4 N11 -179.5(3) . . . . ? C3 N9 N10 K1 -135.6(2) . . . 3_766 ? C3 N9 N10 K2 151.8(2) . . . 1_665 ? C3 N9 N10 C4 0.6(3) . . . . ? C4 N8 C3 N7 -179.6(3) . . . . ? C4 N8 C3 N9 1.4(4) . . . . ?