#------------------------------------------------------------------------------ #$Date: 2018-01-17 07:26:35 +0200 (Wed, 17 Jan 2018) $ #$Revision: 205299 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/22/99/7229990.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_7229990 loop_ _publ_author_name 'Yepremyan, Akop' 'Mehmood, Arshad' 'Brewer, Samantha M.' 'Barnett, Madalyn M.' 'Janesko, Benjamin G.' 'Akkaraju, Giridhar' 'Simanek, Eric E.' 'Green, Kayla N.' _publ_section_title ; A new triazine bearing a pyrazolone group capable of copper, nickel, and zinc chelation ; _journal_issue 6 _journal_name_full 'RSC Advances' _journal_page_first 3024 _journal_paper_doi 10.1039/C7RA09459K _journal_volume 8 _journal_year 2018 _chemical_formula_moiety 'C22 H32 N16 Ni O4, 0.269(O2), 2(Cl), 2.462(O)' _chemical_formula_sum 'C22 H32 Cl2 N16 Ni O7' _chemical_formula_weight 762.23 _chemical_melting_point ? _chemical_name_common none _space_group_crystal_system triclinic _space_group_IT_number 2 _space_group_name_Hall '-P 1' _space_group_name_H-M_alt 'P -1' _symmetry_space_group_name_Hall '-P 1' _symmetry_space_group_name_H-M 'P -1' _atom_sites_solution_hydrogens mixed _atom_sites_solution_primary mixed _audit_creation_date 2017-08-06 _audit_creation_method SHELXL-2014/7 _audit_update_record ; 2017-06-09 deposited with the CCDC. 2018-01-02 downloaded from the CCDC. ; _cell_angle_alpha 74.133(8) _cell_angle_beta 70.006(8) _cell_angle_gamma 64.470(7) _cell_formula_units_Z 2 _cell_length_a 12.261(3) _cell_length_b 12.784(4) _cell_length_c 13.598(4) _cell_measurement_reflns_used 9953 _cell_measurement_temperature 100(2) _cell_measurement_theta_max 26.928 _cell_measurement_theta_min 3.053 _cell_volume 1787.3(9) _computing_cell_refinement 'Apex3 (Bruker AXS Inc., 2016)' _computing_data_collection 'Apex3 (Bruker AXS Inc., 2016)' _computing_data_reduction 'SAINT V8.32B (Bruker AXS Inc., 2013)' _computing_molecular_graphics ; ORTEp-3 (Farrugia, 2012) and Olex2 (Dolomanov et al., 2009) ; _computing_publication_material 'WinGX2014.1 (Farrugia, 2012)' _computing_structure_refinement 'SHELXL-2014/7 (Sheldrick, 2014)' _computing_structure_solution 'SHELXT (Sheldrick, 2013)' _diffrn_ambient_temperature 100(2) _diffrn_detector 'Photon 100 CMOS detector' _diffrn_detector_area_resol_mean 10.24 _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.983 _diffrn_measurement_device_type ; Bruker D8 Quest with Photon 100 CMOS Detector ; _diffrn_measurement_method ; \f and \w scans with 0.5 deg/frame and 20 seconds of exposure time. Detector was at 50mm from crystal. ; _diffrn_radiation_monochromator 'Multi-layer X-ray mirror' _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.1408 _diffrn_reflns_av_unetI/netI 0.1003 _diffrn_reflns_Laue_measured_fraction_full 0.998 _diffrn_reflns_Laue_measured_fraction_max 0.983 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_number 68001 _diffrn_reflns_point_group_measured_fraction_full 0.998 _diffrn_reflns_point_group_measured_fraction_max 0.983 _diffrn_reflns_theta_full 25.000 _diffrn_reflns_theta_max 27.310 _diffrn_reflns_theta_min 2.796 _diffrn_source 'fine-focused sealed tube' _exptl_absorpt_coefficient_mu 0.754 _exptl_absorpt_correction_T_max 0.944 _exptl_absorpt_correction_T_min 0.868 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.1185 before and 0.0752 after correction. The Ratio of minimum to maximum transmission is 0.9073. The \l/2 correction factor is 0.00150. ; _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.416 _exptl_crystal_density_meas ? _exptl_crystal_density_method none _exptl_crystal_description Needle _exptl_crystal_F_000 788 _exptl_crystal_size_max 0.288 _exptl_crystal_size_mid 0.156 _exptl_crystal_size_min 0.076 _exptl_transmission_factor_max 0.977 _exptl_transmission_factor_min 0.968 _refine_diff_density_max 2.176 _refine_diff_density_min -1.198 _refine_diff_density_rms 0.202 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.099 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 462 _refine_ls_number_reflns 7929 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.099 _refine_ls_R_factor_all 0.1972 _refine_ls_R_factor_gt 0.1218 _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^)+(0.1734P)^2^+12.0684P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.3076 _refine_ls_wR_factor_ref 0.3581 _reflns_Friedel_coverage 0.000 _reflns_number_gt 4657 _reflns_number_total 7929 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file c7ra09459k5.cif _cod_data_source_block Complex-7 _cod_depositor_comments ; The following automatic conversions were performed: '_chemical_melting_point' value 'not measured' was changed to '?' - the value is undefined or not given. '_exptl_crystal_density_meas' value 'not measured' was changed to '?' - the value is perceived as not measured. Automatic conversion script Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas ; _cod_database_code 7229990 _shelx_shelxl_version_number 2014/7 _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 0.812 _shelx_estimated_absorpt_t_max 0.945 _exptl_absorpt_special_details ; The crystal was mounted using Paratone-N oil (cryoprotectant) on the tip of MiTeGen MicroLoops LD?. It was placed on magnetic head of goniometer directly into the cold gas stream of a liquid-nitrogen based cryostat. ; _shelx_res_file ; shelx.res created by SHELXL-2014/7 TITL AMakop13_0m_a.res in P-1 CELL 0.71073 12.2608 12.7844 13.598 74.133 70.006 64.47 ZERR 4 0.0034 0.0036 0.0038 0.008 0.008 0.007 LATT 1 SFAC C H Cl N Ni O UNIT 44 64 4 32 2 14 EQIV $1 1-X,-Y,1-Z EQIV $2 -X,1-Y,2-Z EQIV $3 1-X,-Y,2-Z EQIV $4 1-X,1-Y,1-Z EQIV $5 1+X,+Y,+Z EADP Cl1A Cl1B EADP O5A O5B EADP O6A O6B EADP C19A C19B EADP C20A C20B EADP C22A C22B EADP O4A O4B L.S. 50 PLAN 50 SIZE 0.076 0.156 0.288 TEMP -173.16 HTAB N8 O5A_$1 HTAB N8 O5B_$1 HTAB N9 Cl2_$2 HTAB N9 O6A HTAB N9 O6A_$3 HTAB N9 O6B HTAB N7 Cl1A HTAB N7 Cl1B HTAB N10 O1_$5 HTAB N16 O2_$4 HTAB N5 Cl2 HTAB BOND $H LIST 4 fmap 2 acta 50 MERG 2 REM REM REM WGHT 0.173400 12.068400 FVAR 0.39580 0.53812 PART 1 CL1A 3 0.345824 -0.141564 0.715010 21.00000 0.51932 0.06863 = 0.12788 -0.00225 -0.02889 -0.04391 O5A 6 0.372264 -0.076415 0.500741 21.00000 0.17517 0.02176 = 0.04600 -0.01275 0.04683 -0.01726 O6A 6 0.484289 -0.006982 0.972511 21.00000 0.06754 C19A 1 0.935764 0.334515 0.424391 21.00000 0.03064 AFIX 23 H19A 2 0.921005 0.285098 0.389398 21.00000 -1.20000 H19B 2 0.888807 0.417161 0.398861 21.00000 -1.20000 AFIX 0 C20A 1 1.058726 0.316769 0.389539 21.00000 0.04703 0.08347 = 0.02896 -0.00002 -0.00541 -0.04920 AFIX 23 H20A 2 1.068534 0.375375 0.325695 21.00000 -1.20000 H20B 2 1.102712 0.238906 0.365778 21.00000 -1.20000 AFIX 0 C21A 1 0.968884 0.266707 0.603019 21.00000 0.02769 AFIX 23 H21A 2 0.923473 0.262214 0.678892 21.00000 -1.20000 H21B 2 1.029953 0.187327 0.588989 21.00000 -1.20000 AFIX 0 C22A 1 1.032267 0.347829 0.575601 21.00000 0.04803 0.07349 = 0.04154 0.00575 -0.02692 -0.03634 AFIX 23 H22A 2 1.080712 0.332130 0.626743 21.00000 -1.20000 H22B 2 0.972024 0.430054 0.573108 21.00000 -1.20000 AFIX 0 O4A 6 1.126374 0.320629 0.456127 21.00000 0.01482 0.07058 = 0.03060 -0.01322 0.00115 -0.01999 PART 0 PART 2 CL1B 3 0.338050 -0.140254 0.716356 -21.00000 0.51932 0.06863 = 0.12788 -0.00225 -0.02889 -0.04391 O5B 6 0.611780 -0.137249 0.534380 -21.00000 0.17517 0.02176 = 0.04600 -0.01275 0.04683 -0.01726 O6B 6 0.539495 -0.019929 0.934442 -21.00000 0.06754 C19B 1 0.919015 0.385578 0.430578 -21.00000 0.03064 AFIX 23 H19C 2 0.933701 0.341243 0.374911 -21.00000 -1.20000 H19D 2 0.844165 0.457714 0.424526 -21.00000 -1.20000 AFIX 0 C20B 1 0.995642 0.413347 0.408258 -21.00000 0.04703 0.08347 = 0.02896 -0.00002 -0.00541 -0.04920 AFIX 23 H20C 2 0.959379 0.499679 0.404471 -21.00000 -1.20000 H20D 2 1.041714 0.396853 0.335136 -21.00000 -1.20000 AFIX 0 C21B 1 0.947153 0.317612 0.611282 -21.00000 0.02688 AFIX 23 H21C 2 0.922458 0.275465 0.682780 -21.00000 -1.20000 H21D 2 0.927166 0.399803 0.617028 -21.00000 -1.20000 AFIX 0 C22B 1 1.089500 0.256084 0.558640 -21.00000 0.04803 0.07349 = 0.04154 0.00575 -0.02692 -0.03634 AFIX 23 H22C 2 1.109022 0.184499 0.530580 -21.00000 -1.20000 H22D 2 1.144125 0.240014 0.604661 -21.00000 -1.20000 AFIX 0 O4B 6 1.087420 0.369785 0.467348 -21.00000 0.01482 0.07058 = 0.03060 -0.01322 0.00115 -0.01999 PART 0 NI1 5 0.364853 0.299474 0.720626 11.00000 0.01835 0.03403 = 0.03116 -0.00704 -0.00033 -0.01321 O1 6 -0.335301 0.171682 0.987336 11.00000 0.03034 0.05620 = 0.04557 -0.00950 -0.01394 -0.01389 O2 6 0.287191 0.469561 0.749184 11.00000 0.02507 0.03633 = 0.02511 -0.00658 -0.00211 -0.01793 O3 6 0.320042 0.350795 0.579447 11.00000 0.02480 0.05726 = 0.03078 -0.01687 0.00112 -0.02410 N1 4 -0.116043 0.216389 0.904187 11.00000 0.02705 0.03708 = 0.06749 -0.00868 -0.00113 -0.01624 N2 4 0.095442 0.151360 0.832278 11.00000 0.02374 0.02781 = 0.03738 -0.00317 -0.00188 -0.01281 N3 4 -0.019997 0.347550 0.871446 11.00000 0.02033 0.03030 = 0.04693 -0.00874 0.00199 -0.01102 N4 4 0.198676 0.283039 0.796010 11.00000 0.02154 0.02492 = 0.01806 -0.00398 -0.00453 -0.00871 N5 4 -0.027652 0.555325 0.881058 11.00000 0.02358 0.03088 = 0.03021 -0.00859 0.00229 -0.01004 N6 4 0.083411 0.472145 0.837115 11.00000 0.02308 0.03005 = 0.02426 -0.00792 -0.00150 -0.01124 N7 4 0.303215 0.096770 0.753935 11.00000 0.02376 0.02297 = 0.03738 -0.00390 -0.00453 -0.00756 N8 4 0.411262 0.125490 0.705959 11.00000 0.01896 0.04273 = 0.05690 -0.01943 0.00784 -0.01181 AFIX 23 H8A 2 0.439192 0.116765 0.636380 11.00000 -1.20000 H8B 2 0.473219 0.076766 0.738219 11.00000 -1.20000 AFIX 0 N9 4 0.441754 0.245935 0.850147 11.00000 0.02600 0.03400 = 0.03181 -0.00082 -0.00107 -0.01810 AFIX 23 H9A 2 0.396775 0.298026 0.896966 11.00000 -1.20000 H9B 2 0.439918 0.174400 0.883791 11.00000 -1.20000 AFIX 0 N10 4 0.566481 0.240075 0.812314 11.00000 0.01918 0.05301 = 0.02738 0.00124 -0.00711 -0.01366 N11 4 0.534012 0.306405 0.647199 11.00000 0.02285 0.03227 = 0.02175 -0.00366 -0.00662 -0.01074 N12 4 0.727824 0.272230 0.678573 11.00000 0.02650 0.04750 = 0.02837 -0.00435 -0.00663 -0.02008 N13 4 0.697208 0.341470 0.503094 11.00000 0.01902 0.04312 = 0.02793 -0.00951 -0.00016 -0.01626 N14 4 0.880655 0.312406 0.536439 11.00000 0.02190 0.07342 = 0.03020 -0.00311 -0.00658 -0.02762 N15 4 0.509040 0.374448 0.476489 11.00000 0.02109 0.03476 = 0.02265 -0.00985 -0.00088 -0.01435 N16 4 0.557827 0.401414 0.369560 11.00000 0.02492 0.04154 = 0.02344 -0.00844 -0.00432 -0.01843 C1 1 -0.217233 0.076020 0.981469 11.00000 0.03161 0.04735 = 0.07414 -0.00593 -0.01434 -0.01767 AFIX 23 H1A 2 -0.224200 0.005595 0.971244 11.00000 -1.20000 H1B 2 -0.193996 0.058010 1.048842 11.00000 -1.20000 AFIX 0 C2 1 -0.330098 0.272444 1.005339 11.00000 0.02505 0.05629 = 0.07021 -0.02853 -0.01268 -0.00713 AFIX 23 H2A 2 -0.308298 0.255330 1.073254 11.00000 -1.20000 H2B 2 -0.413703 0.336144 1.011417 11.00000 -1.20000 AFIX 0 C3 1 -0.118994 0.104443 0.893393 11.00000 0.04090 0.03861 = 0.06606 -0.01561 0.00256 -0.02028 AFIX 23 H3A 2 -0.136344 0.112812 0.825105 11.00000 -1.20000 H3B 2 -0.036750 0.040322 0.894485 11.00000 -1.20000 AFIX 0 C4 1 -0.239408 0.311568 0.921645 11.00000 0.03377 0.04023 = 0.05764 -0.01048 -0.01142 -0.00629 AFIX 23 H4A 2 -0.233526 0.378109 0.940551 11.00000 -1.20000 H4B 2 -0.267124 0.339303 0.855534 11.00000 -1.20000 AFIX 0 C5 1 -0.011052 0.237773 0.868295 11.00000 0.02465 0.03212 = 0.04232 -0.00538 -0.00268 -0.01241 C6 1 0.196959 0.177738 0.795907 11.00000 0.02036 0.02546 = 0.02755 -0.00126 -0.00924 -0.00766 C7 1 0.087872 0.360929 0.835540 11.00000 0.02303 0.03070 = 0.01830 0.00030 -0.00543 -0.01333 C8 1 -0.113553 0.761576 0.907218 11.00000 0.05106 0.03395 = 0.04481 -0.01625 -0.00448 -0.01268 AFIX 137 H8C 2 -0.146163 0.812667 0.847138 11.00000 -1.50000 H8D 2 -0.083024 0.802804 0.936346 11.00000 -1.50000 H8E 2 -0.180376 0.740596 0.961951 11.00000 -1.50000 AFIX 0 C9 1 -0.009108 0.653440 0.871170 11.00000 0.04260 0.03139 = 0.02436 -0.00515 -0.00906 -0.01080 C10 1 0.114172 0.636719 0.822529 11.00000 0.03861 0.03616 = 0.02866 -0.00607 -0.00573 -0.01905 AFIX 43 H10A 2 0.151262 0.692792 0.808161 11.00000 -1.20000 AFIX 0 C11 1 0.175649 0.522555 0.797812 11.00000 0.02593 0.03550 = 0.02143 -0.00403 -0.00137 -0.01741 C12 1 0.389103 0.373506 0.491860 11.00000 0.01689 0.04000 = 0.03692 -0.01507 -0.00068 -0.01503 C13 1 0.368635 0.405031 0.390476 11.00000 0.02627 0.05050 = 0.02812 -0.01270 -0.00745 -0.01823 AFIX 43 H13 2 0.295997 0.412544 0.374077 11.00000 -1.20000 AFIX 0 C14 1 0.472085 0.423161 0.318975 11.00000 0.01946 0.03606 = 0.02601 -0.01411 -0.00365 -0.00976 C15 1 0.498714 0.458991 0.202700 11.00000 0.02706 0.05204 = 0.02712 -0.00851 -0.00627 -0.01731 AFIX 137 H15A 2 0.485063 0.542567 0.186100 11.00000 -1.50000 H15B 2 0.442846 0.444865 0.175197 11.00000 -1.50000 H15C 2 0.585840 0.413234 0.169911 11.00000 -1.50000 AFIX 0 C16 1 0.585710 0.337168 0.544893 11.00000 0.02865 0.02991 = 0.02732 -0.00949 -0.00725 -0.01298 C17 1 0.612575 0.272565 0.708731 11.00000 0.02414 0.03125 = 0.03838 -0.00783 -0.01023 -0.00772 C18 1 0.766134 0.308071 0.573876 11.00000 0.02550 0.04587 = 0.02545 -0.01165 -0.00626 -0.01362 CL2 3 -0.308970 0.594729 0.962970 11.00000 0.02702 0.05438 = 0.06487 -0.01997 0.00022 -0.01086 O7 6 -0.413713 0.793500 0.796357 11.00000 0.14635 0.13048 = 0.15266 0.05293 -0.06217 -0.08101 H7 2 0.299750 0.023046 0.750138 11.00000 0.02952 H10 2 0.605201 0.205743 0.863760 11.00000 0.03231 H16 2 0.615406 0.423931 0.358829 11.00000 0.02498 H5 2 -0.101030 0.539524 0.906659 11.00000 0.02884 HKLF 4 REM AMakop13_0m_a.res in P-1 REM R1 = 0.1218 for 4657 Fo > 4sig(Fo) and 0.1972 for all 7929 data REM 462 parameters refined using 0 restraints END WGHT 0.1734 12.0618 REM Instructions for potential hydrogen bonds HTAB C19B O3_$4 EQIV $6 -x+2, -y+1, -z+1 HTAB C20B O4B_$6 HTAB N8 O5A_$1 HTAB N8 O5B_$1 HTAB N9 Cl2_$2 HTAB N9 O6A HTAB N9 O6A_$3 HTAB N9 O6B EQIV $7 -x, -y, -z+2 HTAB C2 Cl1A_$7 HTAB C4 Cl2 HTAB C8 Cl2 EQIV $8 x-1, y, z HTAB C13 O4A_$8 HTAB C13 O4B_$8 HTAB C15 N10_$4 HTAB N7 Cl1A HTAB N10 O1_$5 HTAB N16 O2_$4 HTAB N5 Cl2 REM Highest difference peak 2.176, deepest hole -1.198, 1-sigma level 0.202 Q1 1 0.5980 -0.0263 0.8147 11.00000 0.05 2.18 Q2 1 0.7173 -0.0230 0.7030 11.00000 0.05 2.02 Q3 1 0.0272 -0.0603 0.6785 11.00000 0.05 1.91 Q4 1 1.0011 0.0454 0.3636 11.00000 0.05 1.61 Q5 1 0.7123 -0.1579 0.6035 11.00000 0.05 1.53 Q6 1 1.2003 0.0121 0.3232 11.00000 0.05 1.44 Q7 1 0.4603 -0.0617 0.4951 11.00000 0.05 1.40 Q8 1 0.1181 -0.0764 0.6857 11.00000 0.05 1.08 Q9 1 1.1277 0.0038 0.3945 11.00000 0.05 1.07 Q10 1 -0.1106 0.0834 0.9850 11.00000 0.05 1.06 Q11 1 1.0399 -0.0007 0.4726 11.00000 0.05 1.04 Q12 1 -0.2134 0.2878 1.0191 11.00000 0.05 1.03 Q13 1 0.1598 -0.1183 0.7554 11.00000 0.05 1.03 Q14 1 -0.1038 0.1966 0.9787 11.00000 0.05 1.01 Q15 1 1.0373 -0.0223 0.5286 11.00000 0.05 0.98 Q16 1 1.0654 -0.0332 0.5442 11.00000 0.05 0.95 Q17 1 0.3190 -0.0557 0.4582 11.00000 0.05 0.93 Q18 1 0.4994 -0.0336 0.8835 11.00000 0.05 0.84 Q19 1 -0.1978 0.1074 0.9081 11.00000 0.05 0.84 Q20 1 0.3803 0.2242 0.7177 11.00000 0.05 0.82 Q21 1 -0.4037 0.8863 0.8221 11.00000 0.05 0.75 Q22 1 0.2033 -0.0591 0.5851 11.00000 0.05 0.73 Q23 1 0.3040 -0.0764 0.5109 11.00000 0.05 0.71 Q24 1 0.0069 0.2191 0.9264 11.00000 0.05 0.69 Q25 1 0.2421 -0.0424 0.5016 11.00000 0.05 0.68 Q26 1 0.2182 -0.0362 0.4105 11.00000 0.05 0.68 Q27 1 -0.2973 0.6475 0.9048 11.00000 0.05 0.66 Q28 1 0.2998 0.3604 0.7261 11.00000 0.05 0.58 Q29 1 0.9637 0.2812 0.4269 11.00000 0.05 0.57 Q30 1 0.6244 -0.1192 0.5012 11.00000 0.05 0.57 Q31 1 0.5931 -0.1018 0.5231 11.00000 0.05 0.51 Q32 1 -0.3173 0.1397 0.9968 11.00000 0.05 0.51 Q33 1 0.3753 0.3952 0.4418 11.00000 0.05 0.50 Q34 1 -0.0095 0.0352 0.9667 11.00000 0.05 0.47 Q35 1 0.2624 0.4380 0.7304 11.00000 0.05 0.46 Q36 1 0.5267 0.4062 0.1891 11.00000 0.05 0.46 Q37 1 -0.0073 0.3253 0.9286 11.00000 0.05 0.46 Q38 1 0.8687 0.3771 0.3884 11.00000 0.05 0.46 Q39 1 0.0624 0.1643 0.8822 11.00000 0.05 0.45 Q40 1 -0.2970 0.2018 0.9604 11.00000 0.05 0.45 Q41 1 0.2385 0.2799 0.7603 11.00000 0.05 0.44 Q42 1 0.3613 0.3964 0.7306 11.00000 0.05 0.43 Q43 1 0.5540 0.4911 0.1591 11.00000 0.05 0.43 Q44 1 0.2095 0.3012 0.8178 11.00000 0.05 0.43 Q45 1 0.5439 0.3162 0.6102 11.00000 0.05 0.43 Q46 1 0.7272 0.3385 0.4706 11.00000 0.05 0.42 Q47 1 -0.1216 0.1709 0.9006 11.00000 0.05 0.42 Q48 1 -0.0153 0.2989 0.8598 11.00000 0.05 0.42 Q49 1 1.0280 0.3995 0.3865 11.00000 0.05 0.42 Q50 1 0.3325 0.4027 0.5829 11.00000 0.05 0.42 ; _shelx_res_checksum 51093 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, -y, -z' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group Cl1A Cl 0.35(6) -0.14(2) 0.72(3) 0.28(2) Uani 0.538(7) 1 d . . P A 1 O5A O 0.372(2) -0.0764(11) 0.5007(12) 0.108(6) Uani 0.538(7) 1 d . . P A 1 O6A O 0.4843(17) -0.0070(15) 0.9725(14) 0.068(3) Uiso 0.538(7) 1 d . . P A 1 C19A C 0.9358(14) 0.3345(15) 0.4244(12) 0.031(3) Uiso 0.538(7) 1 d . . P A 1 H19A H 0.9210 0.2851 0.3894 0.037 Uiso 0.538(7) 1 calc R U P A 1 H19B H 0.8888 0.4172 0.3989 0.037 Uiso 0.538(7) 1 calc R U P A 1 C20A C 1.0587(17) 0.317(2) 0.3895(13) 0.047(4) Uani 0.538(7) 1 d . . P A 1 H20A H 1.0685 0.3754 0.3257 0.056 Uiso 0.538(7) 1 calc R U P A 1 H20B H 1.1027 0.2389 0.3658 0.056 Uiso 0.538(7) 1 calc R U P A 1 C21A C 0.9689(14) 0.2667(16) 0.6030(12) 0.028(3) Uiso 0.538(7) 1 d . . P A 1 H21A H 0.9235 0.2622 0.6789 0.033 Uiso 0.538(7) 1 calc R U P A 1 H21B H 1.0300 0.1873 0.5890 0.033 Uiso 0.538(7) 1 calc R U P A 1 C22A C 1.0323(18) 0.3478(19) 0.5756(14) 0.048(4) Uani 0.538(7) 1 d . . P A 1 H22A H 1.0807 0.3321 0.6267 0.058 Uiso 0.538(7) 1 calc R U P A 1 H22B H 0.9720 0.4301 0.5731 0.058 Uiso 0.538(7) 1 calc R U P A 1 O4A O 1.1264(14) 0.3206(16) 0.4561(16) 0.038(4) Uani 0.538(7) 1 d . . P A 1 Cl1B Cl 0.34(7) -0.14(3) 0.72(3) 0.28(2) Uani 0.462(7) 1 d . . P A 2 O5B O 0.612(2) -0.1372(13) 0.5344(14) 0.108(6) Uani 0.462(7) 1 d . . P A 2 O6B O 0.5395(19) -0.0199(17) 0.9344(16) 0.068(3) Uiso 0.462(7) 1 d . . P A 2 C19B C 0.9190(17) 0.3856(18) 0.4306(14) 0.031(3) Uiso 0.462(7) 1 d . . P A 2 H19C H 0.9337 0.3412 0.3749 0.037 Uiso 0.462(7) 1 calc R U P A 2 H19D H 0.8442 0.4577 0.4245 0.037 Uiso 0.462(7) 1 calc R U P A 2 C20B C 0.996(2) 0.413(2) 0.4083(16) 0.047(4) Uani 0.462(7) 1 d . . P A 2 H20C H 0.9594 0.4997 0.4045 0.056 Uiso 0.462(7) 1 calc R U P A 2 H20D H 1.0417 0.3969 0.3351 0.056 Uiso 0.462(7) 1 calc R U P A 2 C21B C 0.9472(16) 0.3176(19) 0.6113(14) 0.027(4) Uiso 0.462(7) 1 d . . P A 2 H21C H 0.9225 0.2755 0.6828 0.032 Uiso 0.462(7) 1 calc R U P A 2 H21D H 0.9272 0.3998 0.6170 0.032 Uiso 0.462(7) 1 calc R U P A 2 C22B C 1.089(2) 0.256(2) 0.5586(17) 0.048(4) Uani 0.462(7) 1 d . . P A 2 H22C H 1.1090 0.1845 0.5306 0.058 Uiso 0.462(7) 1 calc R U P A 2 H22D H 1.1441 0.2400 0.6047 0.058 Uiso 0.462(7) 1 calc R U P A 2 O4B O 1.0874(17) 0.3698(19) 0.467(2) 0.038(4) Uani 0.462(7) 1 d . . P A 2 Ni1 Ni 0.36485(8) 0.29947(9) 0.72063(8) 0.0278(3) Uani 1 1 d . . . . . O1 O -0.3353(5) 0.1717(6) 0.9873(5) 0.0433(15) Uani 1 1 d . . . . . O2 O 0.2872(5) 0.4696(5) 0.7492(4) 0.0272(12) Uani 1 1 d . . . . . O3 O 0.3200(5) 0.3508(5) 0.5794(4) 0.0344(13) Uani 1 1 d . . . . . N1 N -0.1160(6) 0.2164(6) 0.9042(7) 0.045(2) Uani 1 1 d . . . . . N2 N 0.0954(6) 0.1514(6) 0.8323(5) 0.0305(15) Uani 1 1 d . . . . . N3 N -0.0200(6) 0.3475(6) 0.8714(6) 0.0343(16) Uani 1 1 d . . . . . N4 N 0.1987(5) 0.2830(5) 0.7960(5) 0.0215(12) Uani 1 1 d . . . . . N5 N -0.0277(6) 0.5553(6) 0.8811(5) 0.0300(15) Uani 1 1 d . . . . . N6 N 0.0834(6) 0.4721(5) 0.8371(5) 0.0258(13) Uani 1 1 d . . . . . N7 N 0.3032(6) 0.0968(6) 0.7539(5) 0.0295(15) Uani 1 1 d . . . . . N8 N 0.4113(6) 0.1255(6) 0.7060(7) 0.0417(18) Uani 1 1 d . . . . . H8A H 0.4392 0.1168 0.6364 0.050 Uiso 1 1 calc R U . . . H8B H 0.4732 0.0768 0.7382 0.050 Uiso 1 1 calc R U . . . N9 N 0.4418(6) 0.2459(6) 0.8501(5) 0.0308(15) Uani 1 1 d . . . . . H9A H 0.3968 0.2980 0.8970 0.037 Uiso 1 1 calc R U . . . H9B H 0.4399 0.1744 0.8838 0.037 Uiso 1 1 calc R U . . . N10 N 0.5665(6) 0.2401(7) 0.8123(6) 0.0344(16) Uani 1 1 d . . . . . N11 N 0.5340(6) 0.3064(6) 0.6472(5) 0.0253(13) Uani 1 1 d . . . . . N12 N 0.7278(6) 0.2722(6) 0.6786(5) 0.0322(15) Uani 1 1 d . . . . . N13 N 0.6972(6) 0.3415(6) 0.5031(5) 0.0290(15) Uani 1 1 d . . . . . N14 N 0.8807(6) 0.3124(7) 0.5364(6) 0.0393(18) Uani 1 1 d . . . . . N15 N 0.5090(5) 0.3744(6) 0.4765(5) 0.0248(13) Uani 1 1 d . . . . . N16 N 0.5578(6) 0.4014(6) 0.3696(5) 0.0275(14) Uani 1 1 d . . . . . C1 C -0.2172(8) 0.0760(9) 0.9815(9) 0.050(3) Uani 1 1 d . . . . . H1A H -0.2242 0.0056 0.9712 0.061 Uiso 1 1 calc R U . . . H1B H -0.1940 0.0580 1.0488 0.061 Uiso 1 1 calc R U . . . C2 C -0.3301(8) 0.2724(9) 1.0053(9) 0.049(2) Uani 1 1 d . . . . . H2A H -0.3083 0.2553 1.0733 0.059 Uiso 1 1 calc R U . . . H2B H -0.4137 0.3361 1.0114 0.059 Uiso 1 1 calc R U . . . C3 C -0.1190(9) 0.1044(8) 0.8934(9) 0.049(2) Uani 1 1 d . . . . . H3A H -0.1363 0.1128 0.8251 0.059 Uiso 1 1 calc R U . . . H3B H -0.0367 0.0403 0.8945 0.059 Uiso 1 1 calc R U . . . C4 C -0.2394(8) 0.3116(8) 0.9216(8) 0.046(2) Uani 1 1 d . . . . . H4A H -0.2335 0.3781 0.9406 0.055 Uiso 1 1 calc R U . . . H4B H -0.2671 0.3393 0.8555 0.055 Uiso 1 1 calc R U . . . C5 C -0.0111(7) 0.2378(7) 0.8683(7) 0.0341(19) Uani 1 1 d . . . . . C6 C 0.1970(6) 0.1777(6) 0.7959(6) 0.0245(16) Uani 1 1 d . . . . . C7 C 0.0879(7) 0.3609(6) 0.8355(6) 0.0236(15) Uani 1 1 d . . . . . C8 C -0.1136(9) 0.7616(8) 0.9072(8) 0.044(2) Uani 1 1 d . . . . . H8C H -0.1462 0.8127 0.8471 0.067 Uiso 1 1 calc R U . . . H8D H -0.0830 0.8028 0.9363 0.067 Uiso 1 1 calc R U . . . H8E H -0.1804 0.7406 0.9620 0.067 Uiso 1 1 calc R U . . . C9 C -0.0091(8) 0.6534(7) 0.8712(6) 0.0336(18) Uani 1 1 d . . . . . C10 C 0.1142(8) 0.6367(7) 0.8225(6) 0.0332(18) Uani 1 1 d . . . . . H10A H 0.1513 0.6928 0.8082 0.040 Uiso 1 1 calc R U . . . C11 C 0.1756(7) 0.5226(7) 0.7978(6) 0.0268(16) Uani 1 1 d . . . . . C12 C 0.3891(7) 0.3735(7) 0.4919(7) 0.0293(17) Uani 1 1 d . . . . . C13 C 0.3686(7) 0.4050(8) 0.3905(6) 0.0319(18) Uani 1 1 d . . . . . H13 H 0.2960 0.4125 0.3741 0.038 Uiso 1 1 calc R U . . . C14 C 0.4721(6) 0.4232(7) 0.3190(6) 0.0259(16) Uani 1 1 d . . . . . C15 C 0.4987(7) 0.4590(8) 0.2027(6) 0.0341(19) Uani 1 1 d . . . . . H15A H 0.4851 0.5426 0.1861 0.051 Uiso 1 1 calc R U . . . H15B H 0.4428 0.4449 0.1752 0.051 Uiso 1 1 calc R U . . . H15C H 0.5858 0.4132 0.1699 0.051 Uiso 1 1 calc R U . . . C16 C 0.5857(7) 0.3372(7) 0.5449(6) 0.0267(16) Uani 1 1 d . . . . . C17 C 0.6126(7) 0.2726(7) 0.7087(7) 0.0310(18) Uani 1 1 d . . . . . C18 C 0.7661(7) 0.3081(7) 0.5739(6) 0.0309(18) Uani 1 1 d . . . . . Cl2 Cl -0.3090(2) 0.5947(2) 0.9630(2) 0.0513(7) Uani 1 1 d . . . . . O7 O -0.4137(14) 0.7935(12) 0.7964(12) 0.142(5) Uani 1 1 d . . . . . H7 H 0.300(7) 0.023(8) 0.750(7) 0.03(2) Uiso 1 1 d . . . . . H10 H 0.605(8) 0.206(8) 0.864(7) 0.03(2) Uiso 1 1 d . . . . . H16 H 0.615(8) 0.424(7) 0.359(6) 0.02(2) Uiso 1 1 d . . . . . H5 H -0.101(8) 0.540(7) 0.907(7) 0.03(2) Uiso 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 Cl1A 0.52(6) 0.069(5) 0.128(8) -0.002(5) -0.029(19) -0.044(14) O5A 0.175(14) 0.022(5) 0.046(7) -0.013(5) 0.047(8) -0.017(7) C20A 0.047(9) 0.083(11) 0.029(7) 0.000(8) -0.005(6) -0.049(8) C22A 0.048(9) 0.073(10) 0.042(8) 0.006(8) -0.027(7) -0.036(8) O4A 0.015(9) 0.071(13) 0.031(6) -0.013(8) 0.001(7) -0.020(7) Cl1B 0.52(6) 0.069(5) 0.128(8) -0.002(5) -0.029(19) -0.044(14) O5B 0.175(14) 0.022(5) 0.046(7) -0.013(5) 0.047(8) -0.017(7) C20B 0.047(9) 0.083(11) 0.029(7) 0.000(8) -0.005(6) -0.049(8) C22B 0.048(9) 0.073(10) 0.042(8) 0.006(8) -0.027(7) -0.036(8) O4B 0.015(9) 0.071(13) 0.031(6) -0.013(8) 0.001(7) -0.020(7) Ni1 0.0183(5) 0.0340(6) 0.0312(6) -0.0070(4) -0.0003(4) -0.0132(4) O1 0.030(3) 0.056(4) 0.046(4) -0.009(3) -0.014(3) -0.014(3) O2 0.025(3) 0.036(3) 0.025(3) -0.007(2) -0.002(2) -0.018(2) O3 0.025(3) 0.057(4) 0.031(3) -0.017(3) 0.001(2) -0.024(3) N1 0.027(4) 0.037(4) 0.067(6) -0.009(4) -0.001(4) -0.016(3) N2 0.024(3) 0.028(3) 0.037(4) -0.003(3) -0.002(3) -0.013(3) N3 0.020(3) 0.030(4) 0.047(4) -0.009(3) 0.002(3) -0.011(3) N4 0.022(3) 0.025(3) 0.018(3) -0.004(2) -0.005(2) -0.009(2) N5 0.024(3) 0.031(4) 0.030(4) -0.009(3) 0.002(3) -0.010(3) N6 0.023(3) 0.030(3) 0.024(3) -0.008(3) -0.002(3) -0.011(3) N7 0.024(3) 0.023(3) 0.037(4) -0.004(3) -0.005(3) -0.008(3) N8 0.019(3) 0.043(4) 0.057(5) -0.019(4) 0.008(3) -0.012(3) N9 0.026(3) 0.034(4) 0.032(4) -0.001(3) -0.001(3) -0.018(3) N10 0.019(3) 0.053(5) 0.027(4) 0.001(3) -0.007(3) -0.014(3) N11 0.023(3) 0.032(3) 0.022(3) -0.004(3) -0.007(3) -0.011(3) N12 0.027(3) 0.048(4) 0.028(4) -0.004(3) -0.007(3) -0.020(3) N13 0.019(3) 0.043(4) 0.028(4) -0.010(3) 0.000(3) -0.016(3) N14 0.022(3) 0.073(5) 0.030(4) -0.003(4) -0.007(3) -0.028(3) N15 0.021(3) 0.035(3) 0.023(3) -0.010(3) -0.001(2) -0.014(3) N16 0.025(3) 0.042(4) 0.023(3) -0.008(3) -0.004(3) -0.018(3) C1 0.032(5) 0.047(6) 0.074(7) -0.006(5) -0.014(5) -0.018(4) C2 0.025(4) 0.056(6) 0.070(7) -0.029(5) -0.013(4) -0.007(4) C3 0.041(5) 0.039(5) 0.066(7) -0.016(5) 0.003(5) -0.020(4) C4 0.034(5) 0.040(5) 0.058(6) -0.010(4) -0.011(4) -0.006(4) C5 0.025(4) 0.032(4) 0.042(5) -0.005(4) -0.003(3) -0.012(3) C6 0.020(3) 0.025(4) 0.028(4) -0.001(3) -0.009(3) -0.008(3) C7 0.023(3) 0.031(4) 0.018(4) 0.000(3) -0.005(3) -0.013(3) C8 0.051(5) 0.034(5) 0.045(6) -0.016(4) -0.004(4) -0.013(4) C9 0.043(5) 0.031(4) 0.024(4) -0.005(3) -0.009(4) -0.011(4) C10 0.039(4) 0.036(4) 0.029(4) -0.006(3) -0.006(4) -0.019(4) C11 0.026(4) 0.036(4) 0.021(4) -0.004(3) -0.001(3) -0.017(3) C12 0.017(3) 0.040(4) 0.037(5) -0.015(4) -0.001(3) -0.015(3) C13 0.026(4) 0.050(5) 0.028(4) -0.013(4) -0.007(3) -0.018(4) C14 0.019(3) 0.036(4) 0.026(4) -0.014(3) -0.004(3) -0.010(3) C15 0.027(4) 0.052(5) 0.027(4) -0.009(4) -0.006(3) -0.017(4) C16 0.029(4) 0.030(4) 0.027(4) -0.009(3) -0.007(3) -0.013(3) C17 0.024(4) 0.031(4) 0.038(5) -0.008(4) -0.010(3) -0.008(3) C18 0.025(4) 0.046(5) 0.025(4) -0.012(4) -0.006(3) -0.014(4) Cl2 0.0270(11) 0.0544(14) 0.0649(17) -0.0200(12) 0.0002(10) -0.0109(10) O7 0.146(11) 0.130(11) 0.153(12) 0.053(9) -0.062(10) -0.081(9) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ni Ni 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 '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 C20A C19A N14 119.4(13) C20A C19A H19A 107.5 N14 C19A H19A 107.5 C20A C19A H19B 107.5 N14 C19A H19B 107.5 H19A C19A H19B 107.0 C19A C20A O4A 121.9(16) C19A C20A H20A 106.8 O4A C20A H20A 106.8 C19A C20A H20B 106.8 O4A C20A H20B 106.8 H20A C20A H20B 106.7 C22A C21A N14 106.4(13) C22A C21A H21A 110.4 N14 C21A H21A 110.4 C22A C21A H21B 110.4 N14 C21A H21B 110.4 H21A C21A H21B 108.6 C21A C22A O4A 102.8(16) C21A C22A H22A 111.2 O4A C22A H22A 111.2 C21A C22A H22B 111.2 O4A C22A H22B 111.2 H22A C22A H22B 109.1 C20A O4A C22A 110.5(13) C20B C19B N14 124.9(19) C20B C19B H19C 106.1 N14 C19B H19C 106.1 C20B C19B H19D 106.1 N14 C19B H19D 106.1 H19C C19B H19D 106.3 C19B C20B O4B 123(2) C19B C20B H20C 106.6 O4B C20B H20C 106.6 C19B C20B H20D 106.6 O4B C20B H20D 106.6 H20C C20B H20D 106.6 N14 C21B C22B 104.3(14) N14 C21B H21C 110.9 C22B C21B H21C 110.9 N14 C21B H21D 110.9 C22B C21B H21D 110.9 H21C C21B H21D 108.9 C21B C22B O4B 91.1(16) C21B C22B H22C 113.4 O4B C22B H22C 113.4 C21B C22B H22D 113.4 O4B C22B H22D 113.4 H22C C22B H22D 110.7 C20B O4B C22B 118.1(19) N11 Ni1 N4 176.9(3) N11 Ni1 O3 90.0(2) N4 Ni1 O3 91.0(2) N11 Ni1 O2 93.4(2) N4 Ni1 O2 89.4(2) O3 Ni1 O2 91.4(2) N11 Ni1 N9 80.1(2) N4 Ni1 N9 98.8(2) O3 Ni1 N9 170.1(2) O2 Ni1 N9 90.2(2) N11 Ni1 N8 97.1(3) N4 Ni1 N8 80.0(2) O3 Ni1 N8 88.7(3) O2 Ni1 N8 169.5(2) N9 Ni1 N8 91.6(3) C2 O1 C1 111.1(7) C11 O2 Ni1 126.5(5) C12 O3 Ni1 125.8(5) C5 N1 C4 121.6(7) C5 N1 C3 121.6(7) C4 N1 C3 113.6(7) C6 N2 C5 115.7(7) C7 N3 C5 113.5(6) C7 N4 C6 114.2(6) C7 N4 Ni1 131.1(5) C6 N4 Ni1 114.3(5) C9 N5 N6 108.7(6) C9 N5 H5 131(5) N6 N5 H5 120(5) N5 N6 C7 119.7(6) N5 N6 C11 108.1(6) C7 N6 C11 132.1(6) C6 N7 N8 119.1(6) C6 N7 H7 117(5) N8 N7 H7 123(5) N7 N8 Ni1 108.7(5) N7 N8 H8A 109.9 Ni1 N8 H8A 109.9 N7 N8 H8B 109.9 Ni1 N8 H8B 109.9 H8A N8 H8B 108.3 N10 N9 Ni1 108.2(5) N10 N9 H9A 110.1 Ni1 N9 H9A 110.1 N10 N9 H9B 110.1 Ni1 N9 H9B 110.1 H9A N9 H9B 108.4 C17 N10 N9 119.9(7) C17 N10 H10 130(6) N9 N10 H10 110(6) C16 N11 C17 112.8(6) C16 N11 Ni1 131.2(5) C17 N11 Ni1 115.9(5) C17 N12 C18 113.6(7) C16 N13 C18 113.9(7) C18 N14 C19A 121.7(8) C18 N14 C21A 121.8(9) C19A N14 C21A 114.9(10) C18 N14 C19B 122.3(9) C18 N14 C21B 120.5(9) C19B N14 C21B 106.8(11) N16 N15 C16 119.2(6) N16 N15 C12 108.2(6) C16 N15 C12 131.7(7) C14 N16 N15 108.6(6) C14 N16 H16 135(6) N15 N16 H16 111(6) O1 C1 C3 111.0(8) O1 C1 H1A 109.4 C3 C1 H1A 109.4 O1 C1 H1B 109.4 C3 C1 H1B 109.4 H1A C1 H1B 108.0 O1 C2 C4 112.2(8) O1 C2 H2A 109.2 C4 C2 H2A 109.2 O1 C2 H2B 109.2 C4 C2 H2B 109.2 H2A C2 H2B 107.9 C1 C3 N1 109.3(8) C1 C3 H3A 109.8 N1 C3 H3A 109.8 C1 C3 H3B 109.8 N1 C3 H3B 109.8 H3A C3 H3B 108.3 C2 C4 N1 110.9(8) C2 C4 H4A 109.5 N1 C4 H4A 109.5 C2 C4 H4B 109.5 N1 C4 H4B 109.5 H4A C4 H4B 108.1 N1 C5 N2 118.1(7) N1 C5 N3 117.4(7) N2 C5 N3 124.5(7) N7 C6 N2 117.6(7) N7 C6 N4 117.8(6) N2 C6 N4 124.6(7) N3 C7 N4 127.5(7) N3 C7 N6 115.6(6) N4 C7 N6 116.9(6) C9 C8 H8C 109.5 C9 C8 H8D 109.5 H8C C8 H8D 109.5 C9 C8 H8E 109.5 H8C C8 H8E 109.5 H8D C8 H8E 109.5 N5 C9 C10 109.8(7) N5 C9 C8 121.5(8) C10 C9 C8 128.6(8) C9 C10 C11 108.0(7) C9 C10 H10A 126.0 C11 C10 H10A 126.0 O2 C11 C10 131.0(7) O2 C11 N6 123.6(7) C10 C11 N6 105.3(6) O3 C12 C13 130.0(7) O3 C12 N15 124.7(7) C13 C12 N15 105.3(6) C14 C13 C12 108.1(7) C14 C13 H13 125.9 C12 C13 H13 125.9 N16 C14 C13 109.6(7) N16 C14 C15 119.9(7) C13 C14 C15 130.5(7) C14 C15 H15A 109.5 C14 C15 H15B 109.5 H15A C15 H15B 109.5 C14 C15 H15C 109.5 H15A C15 H15C 109.5 H15B C15 H15C 109.5 N13 C16 N11 127.5(7) N13 C16 N15 116.4(7) N11 C16 N15 116.0(6) N12 C17 N11 126.8(8) N12 C17 N10 117.3(7) N11 C17 N10 115.8(7) N14 C18 N12 117.9(7) N14 C18 N13 116.9(7) N12 C18 N13 125.2(7) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 O6A O6A 1.03(3) 2_657 C19A C20A 1.35(2) . C19A N14 1.443(17) . C19A H19A 0.9900 . C19A H19B 0.9900 . C20A O4A 1.44(3) . C20A H20A 0.9900 . C20A H20B 0.9900 . C21A C22A 1.45(2) . C21A N14 1.472(16) . C21A H21A 0.9900 . C21A H21B 0.9900 . C22A O4A 1.67(3) . C22A H22A 0.9900 . C22A H22B 0.9900 . O6B O6B 1.81(4) 2_657 C19B C20B 1.07(2) . C19B N14 1.532(19) . C19B H19C 0.9900 . C19B H19D 0.9900 . C20B O4B 1.43(3) . C20B H20C 0.9900 . C20B H20D 0.9900 . C21B N14 1.535(18) . C21B C22B 1.56(3) . C21B H21C 0.9900 . C21B H21D 0.9900 . C22B O4B 1.63(3) . C22B H22C 0.9900 . C22B H22D 0.9900 . Ni1 N11 2.000(6) . Ni1 N4 2.017(6) . Ni1 O3 2.035(6) . Ni1 O2 2.052(5) . Ni1 N9 2.093(7) . Ni1 N8 2.094(7) . O1 C2 1.406(11) . O1 C1 1.430(11) . O2 C11 1.263(9) . O3 C12 1.246(9) . N1 C5 1.331(10) . N1 C4 1.467(11) . N1 C3 1.495(11) . N2 C6 1.326(9) . N2 C5 1.334(10) . N3 C7 1.313(9) . N3 C5 1.371(10) . N4 C7 1.324(9) . N4 C6 1.356(9) . N5 C9 1.333(11) . N5 N6 1.373(9) . N5 H5 0.94(9) . N6 C7 1.405(10) . N6 C11 1.417(9) . N7 C6 1.322(10) . N7 N8 1.419(9) . N7 H7 0.98(9) . N8 H8A 0.9100 . N8 H8B 0.9100 . N9 N10 1.412(9) . N9 H9A 0.9100 . N9 H9B 0.9100 . N10 C17 1.347(11) . N10 H10 0.89(9) . N11 C16 1.343(10) . N11 C17 1.345(10) . N12 C17 1.328(10) . N12 C18 1.352(10) . N13 C16 1.308(9) . N13 C18 1.358(10) . N14 C18 1.340(10) . N15 N16 1.378(9) . N15 C16 1.395(10) . N15 C12 1.418(9) . N16 C14 1.339(10) . N16 H16 0.83(9) . C1 C3 1.473(13) . C1 H1A 0.9900 . C1 H1B 0.9900 . C2 C4 1.444(14) . C2 H2A 0.9900 . C2 H2B 0.9900 . C3 H3A 0.9900 . C3 H3B 0.9900 . C4 H4A 0.9900 . C4 H4B 0.9900 . C8 C9 1.485(12) . C8 H8C 0.9800 . C8 H8D 0.9800 . C8 H8E 0.9800 . C9 C10 1.372(12) . C10 C11 1.399(11) . C10 H10A 0.9500 . C12 C13 1.404(12) . C13 C14 1.376(11) . C13 H13 0.9500 . C14 C15 1.482(11) . C15 H15A 0.9800 . C15 H15B 0.9800 . C15 H15C 0.9800 . 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 N8 H8A O5A 0.91 2.37 3.125(16) 139.8 2_656 N8 H8A O5B 0.91 2.52 3.33(2) 148.4 2_656 N9 H9A Cl2 0.91 2.33 3.225(7) 168.6 2_567 N9 H9B O6A 0.91 2.23 3.113(19) 164.5 . N9 H9B O6A 0.91 2.55 3.324(19) 143.2 2_657 N9 H9B O6B 0.91 2.27 3.10(2) 150.8 . N7 H7 Cl1A 0.98(9) 2.1(4) 3.0(4) 163(19) . N7 H7 Cl1B 0.98(9) 2.1(5) 3.0(5) 165(21) . N10 H10 O1 0.89(9) 1.93(10) 2.792(9) 165(8) 1_655 N16 H16 O2 0.83(9) 2.13(9) 2.844(8) 144(8) 2_666 N5 H5 Cl2 0.94(9) 2.23(9) 3.094(7) 152(7) .