#------------------------------------------------------------------------------ #$Date: 2016-08-07 11:22:46 +0300 (Sun, 07 Aug 2016) $ #$Revision: 185227 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/22/51/7225192.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_7225192 loop_ _publ_author_name 'Beldon, Patrick J.' 'Henke, Sebastian' 'Monserrat, Bartomeu' 'Tominaka, Satoshi' 'Stock, Norbert' 'Cheetham, Anthony K.' _publ_section_title ; Transition metal coordination complexes of chrysazin ; _journal_issue 27 _journal_name_full CrystEngComm _journal_page_first 5121 _journal_paper_doi 10.1039/C5CE00792E _journal_volume 18 _journal_year 2016 _chemical_formula_moiety 'C40 H36 N8 Ni2 O20' _chemical_formula_sum 'C40 H36 N8 Ni2 O20' _chemical_formula_weight 1066.19 _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_Hall '-P 2yn' _space_group_name_H-M_alt 'P 1 21/n 1' _symmetry_space_group_name_Hall '-P 2yn' _symmetry_space_group_name_H-M 'P 1 21/n 1' _atom_sites_solution_hydrogens geom _audit_creation_date 2016-01-18 _audit_creation_method ; Olex2 1.2 (compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103) ; _audit_update_record ; 2016-04-20 deposited with the CCDC. 2016-05-11 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 99.517(6) _cell_angle_gamma 90 _cell_formula_units_Z 2 _cell_length_a 9.5780(7) _cell_length_b 11.0933(8) _cell_length_c 20.1508(14) _cell_measurement_reflns_used 13941 _cell_measurement_temperature 100 _cell_measurement_theta_max 27.5 _cell_measurement_theta_min 2.1 _cell_volume 2111.6(3) _computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 (Dolomanov et al., 2009)' _computing_structure_refinement 'ShelXL (Sheldrick, 2015)' _diffrn_ambient_temperature 100 _diffrn_detector_area_resol_mean 28.5714 _diffrn_measured_fraction_theta_full 0.979 _diffrn_measured_fraction_theta_max 0.979 _diffrn_measurement_details ; scan: Number of images: 108 Slice: -35.0000 - 73.0000 Image width: 1.0000 Exp time: 90.0000 Rotation axis: Omega Omega: 0.0000 Kappa: 72.0000 Phi: 150.0000 XTD: 45.1653 2theta: -16.9738 scan: Number of images: 91 Slice: -69.0000 - 22.0000 Image width: 1.0000 Exp time: 90.0000 Rotation axis: Omega Omega: 0.0000 Kappa: -72.0000 Phi: 30.0000 XTD: 45.1653 2theta: -16.9738 scan: Number of images: 90 Slice: -68.0000 - 22.0000 Image width: 1.0000 Exp time: 90.0000 Rotation axis: Omega Omega: 0.0000 Kappa: -72.0000 Phi: -150.0000 XTD: 45.1653 2theta: -16.9738 scan: Number of images: 64 Slice: -56.0000 - 8.0000 Image width: 1.0000 Exp time: 90.0000 Rotation axis: Omega Omega: 0.0000 Kappa: 0.0000 Phi: -180.0000 XTD: 45.1653 2theta: -16.9738 scan: Number of images: 20 Slice: -2.0000 - 18.0000 Image width: 1.0000 Exp time: 90.0000 Rotation axis: Omega Omega: 0.0000 Kappa: -36.0000 Phi: -150.0000 XTD: 45.1653 2theta: -16.9738 scan: Number of images: 95 Slice: -63.0000 - 32.0000 Image width: 1.0000 Exp time: 90.0000 Rotation axis: Omega Omega: 0.0000 Kappa: 18.0000 Phi: -90.0000 XTD: 45.1653 2theta: -16.9738 ; _diffrn_measurement_device_type 'Rigaku Saturn724+ (2x2 bin mode)' _diffrn_measurement_method 'profile data from \w-scans' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71075 _diffrn_reflns_av_R_equivalents 0.117 _diffrn_reflns_av_unetI/netI 0.063 _diffrn_reflns_Laue_measured_fraction_full 0.979 _diffrn_reflns_Laue_measured_fraction_max 0.979 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_number 15440 _diffrn_reflns_point_group_measured_fraction_full 0.979 _diffrn_reflns_point_group_measured_fraction_max 0.979 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 27.453 _diffrn_reflns_theta_min 2.752 _exptl_absorpt_coefficient_mu 0.988 _exptl_absorpt_correction_T_max 1.00 _exptl_absorpt_correction_T_min 0.632 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'Blessing, Acta Cryst. A51 (1995) 33-38' _exptl_crystal_colour red _exptl_crystal_colour_primary red _exptl_crystal_density_diffrn 1.677 _exptl_crystal_description plate _exptl_crystal_F_000 1096 _exptl_crystal_size_max 0.04 _exptl_crystal_size_mid 0.04 _exptl_crystal_size_min 0.01 _refine_diff_density_max 0.951 _refine_diff_density_min -0.659 _refine_diff_density_rms 0.129 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.135 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 320 _refine_ls_number_reflns 4722 _refine_ls_number_restraints 30 _refine_ls_restrained_S_all 1.137 _refine_ls_R_factor_all 0.1422 _refine_ls_R_factor_gt 0.0765 _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^)+(0.0486P)^2^+6.9532P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1479 _refine_ls_wR_factor_ref 0.1696 _reflns_Friedel_coverage 0.000 _reflns_number_gt 2879 _reflns_number_total 4722 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file c5ce00792e2.cif _cod_data_source_block NiNOChrys-1 _cod_depositor_comments 'Adding full bibliography for 7225182--7225192.cif.' _cod_database_code 7225192 _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. ; _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups At 1.5 times of: All C(H,H,H) groups 2. Uiso/Uaniso restraints and constraints Uanis(C3) \\sim Ueq, Uanis(C4) \\sim Ueq, Uanis(C6) \\sim Ueq, Uanis(O2) \\sim Ueq, Uanis(O5) \\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.01 3.a Aromatic/amide H refined with riding coordinates: C2(H2), C3(H3), C12(H12), C13(H13), C15(H15), C18(H18) 3.b Idealised Me refined as rotating group: C16(H16A,H16B,H16C), C17(H17A,H17B,H17C), C19(H19A,H19B,H19C), C20(H20A,H20B, H20C) ; _shelx_res_file ; TITL NINOCHRYS-1 CELL 0.71075 9.578 11.0933 20.1508 90 99.517 90 ZERR 2 0.0007 0.0008 0.0014 0 0.006 0 LATT 1 SYMM 0.5-X,0.5+Y,0.5-Z SFAC C H N Ni O UNIT 80 72 16 4 40 ISOR 0.005 0.01 C3 C4 C6 O2 O5 L.S. 4 PLAN 20 TEMP -173.15 MORE -1 BOND $H CONF fmap 2 53 acta REM REM REM WGHT 0.048600 6.953200 FVAR 0.58219 NI1 4 0.112101 0.512999 0.563016 11.00000 0.01681 0.00456 = 0.01965 0.00037 0.00264 -0.00188 O1 5 0.179781 0.661675 0.612715 11.00000 0.02336 0.00646 = 0.02232 0.00149 0.00581 -0.00313 O2 5 -0.012164 0.625683 0.495290 11.00000 0.01817 0.00441 = 0.02338 0.00191 0.00405 -0.00210 O3 5 -0.226199 0.616422 0.386666 11.00000 0.02143 0.00831 = 0.02602 0.00306 0.00373 -0.00189 O4 5 0.232947 0.965197 0.384394 11.00000 0.02903 0.01628 = 0.03289 0.00227 0.01301 -0.00309 O5 5 0.432528 1.140936 0.527003 11.00000 0.03284 0.02215 = 0.05690 0.00252 -0.00425 -0.01796 O6 5 0.220855 1.159689 0.468285 11.00000 0.03591 0.00802 = 0.04024 0.00328 0.00842 0.00233 O7 5 0.016260 1.126410 0.337909 11.00000 0.04809 0.00715 = 0.03749 -0.00237 0.01370 -0.00135 O8 5 -0.007767 1.049865 0.237007 11.00000 0.04295 0.02441 = 0.02772 0.00562 0.00919 -0.00554 O9 5 -0.032617 0.489379 0.628521 11.00000 0.02297 0.01116 = 0.02374 -0.00096 0.00640 -0.00208 O10 5 0.259890 0.539516 0.502229 11.00000 0.01916 0.00914 = 0.02256 0.00118 0.00636 -0.00179 N1 3 0.312188 1.102654 0.506449 11.00000 0.03223 0.01157 = 0.02869 -0.00099 0.00358 -0.00641 N2 3 -0.012550 1.041782 0.297180 11.00000 0.02238 0.01126 = 0.02421 0.00483 0.00392 0.00148 N3 3 -0.107787 0.551653 0.724247 11.00000 0.02630 0.01083 = 0.02968 -0.00454 0.01284 -0.00206 N4 3 0.390913 0.478539 0.424477 11.00000 0.02242 0.00687 = 0.02527 -0.00214 0.00740 -0.00128 C1 1 0.199555 0.762420 0.583754 11.00000 0.01912 0.00797 = 0.02547 -0.00483 0.00839 -0.00160 C2 1 0.295898 0.846605 0.623070 11.00000 0.02384 0.01260 = 0.02454 -0.00101 0.00078 0.00344 AFIX 43 H2 2 0.335607 0.826447 0.668059 11.00000 -1.20000 AFIX 0 C3 1 0.330863 0.953987 0.597025 11.00000 0.01860 0.00841 = 0.03182 -0.00412 -0.00205 -0.00617 AFIX 43 H3 2 0.393410 1.007971 0.623842 11.00000 -1.20000 AFIX 0 C4 1 0.273766 0.984177 0.530303 11.00000 0.01724 0.00930 = 0.02911 0.00251 0.00271 -0.00489 C5 1 0.181441 0.909203 0.490451 11.00000 0.01394 0.00440 = 0.03047 -0.00287 0.00718 -0.00124 C6 1 0.137001 0.797651 0.516408 11.00000 0.01678 0.00487 = 0.01901 -0.00299 0.00425 -0.00187 C7 1 0.027076 0.727080 0.473821 11.00000 0.01863 0.00521 = 0.02242 -0.00048 0.00751 -0.00168 C8 1 -0.047009 0.772955 0.409334 11.00000 0.02252 0.00942 = 0.01659 -0.00406 0.00699 -0.00371 C9 1 0.004917 0.880649 0.382614 11.00000 0.02967 0.00678 = 0.02205 -0.00170 0.01085 0.00011 C10 1 0.145000 0.926124 0.416223 11.00000 0.02321 0.00452 = 0.02247 -0.00097 0.00726 0.00335 C11 1 -0.169999 0.715672 0.370231 11.00000 0.02143 0.00582 = 0.02473 -0.00065 0.00692 0.00454 C12 1 -0.231703 0.771761 0.308180 11.00000 0.02576 0.01158 = 0.02247 -0.00084 0.00035 -0.00348 AFIX 43 H12 2 -0.313572 0.736026 0.282701 11.00000 -1.20000 AFIX 0 C13 1 -0.179249 0.873002 0.284068 11.00000 0.02753 0.01148 = 0.02052 -0.00069 -0.00003 0.00273 AFIX 43 H13 2 -0.221934 0.906638 0.242252 11.00000 -1.20000 AFIX 0 C14 1 -0.060579 0.926734 0.322354 11.00000 0.02410 0.00860 = 0.01875 0.00455 0.00614 0.00178 C15 1 -0.060244 0.570343 0.667283 11.00000 0.02400 0.00978 = 0.02727 0.00401 0.00609 -0.00136 AFIX 43 H15 2 -0.046005 0.651480 0.654878 11.00000 -1.20000 AFIX 0 C16 1 -0.141987 0.652701 0.766757 11.00000 0.04090 0.00888 = 0.04056 -0.00321 0.02447 0.00248 AFIX 137 H16A 2 -0.081010 0.648571 0.810830 11.00000 -1.50000 H16B 2 -0.241347 0.647060 0.772592 11.00000 -1.50000 H16C 2 -0.126252 0.729381 0.744998 11.00000 -1.50000 AFIX 0 C17 1 -0.130386 0.429565 0.748132 11.00000 0.03711 0.01112 = 0.02937 0.00013 0.00970 -0.00612 AFIX 137 H17A 2 -0.231610 0.416872 0.748224 11.00000 -1.50000 H17B 2 -0.078145 0.419583 0.793894 11.00000 -1.50000 H17C 2 -0.096517 0.370589 0.718251 11.00000 -1.50000 AFIX 0 C18 1 0.309961 0.457933 0.470226 11.00000 0.02024 0.00744 = 0.02596 0.00067 0.00425 -0.00348 AFIX 43 H18 2 0.288451 0.376641 0.479405 11.00000 -1.20000 AFIX 0 C19 1 0.423053 0.603011 0.407449 11.00000 0.02534 0.01280 = 0.02638 0.00204 0.00849 -0.00459 AFIX 137 H19A 2 0.353916 0.630126 0.368971 11.00000 -1.50000 H19B 2 0.518384 0.606569 0.395855 11.00000 -1.50000 H19C 2 0.418320 0.655451 0.446152 11.00000 -1.50000 AFIX 0 C20 1 0.447508 0.379775 0.388372 11.00000 0.02186 0.01700 = 0.03154 -0.00493 0.00754 0.00084 AFIX 137 H20A 2 0.551082 0.384585 0.395610 11.00000 -1.50000 H20B 2 0.410649 0.386407 0.340162 11.00000 -1.50000 H20C 2 0.418583 0.302385 0.405235 11.00000 -1.50000 AFIX 0 HKLF 4 REM NINOCHRYS-1 REM R1 = 0.0765 for 2879 Fo > 4sig(Fo) and 0.1422 for all 4722 data REM 320 parameters refined using 30 restraints END WGHT 0.0487 6.9524 REM Highest difference peak 0.951, deepest hole -0.659, 1-sigma level 0.129 Q1 1 0.0066 0.5183 0.5386 11.00000 0.05 0.95 Q2 1 0.2033 0.5144 0.6015 11.00000 0.05 0.95 Q3 1 0.2208 0.5028 0.5820 11.00000 0.05 0.87 Q4 1 -0.1128 0.6195 0.4640 11.00000 0.05 0.60 Q5 1 -0.1470 0.4809 0.6026 11.00000 0.05 0.55 Q6 1 -0.1754 0.5672 0.6785 11.00000 0.05 0.53 Q7 1 0.3329 0.5378 0.5590 11.00000 0.05 0.53 Q8 1 0.2664 0.9924 0.5658 11.00000 0.05 0.44 Q9 1 -0.3181 0.6426 0.7385 11.00000 0.05 0.43 Q10 1 0.3683 0.3605 0.3602 11.00000 0.05 0.43 Q11 1 0.0366 0.4983 0.6789 11.00000 0.05 0.42 Q12 1 0.0899 1.1100 0.3787 11.00000 0.05 0.42 Q13 1 0.0102 0.5802 0.6025 11.00000 0.05 0.41 Q14 1 0.0170 0.9307 0.2554 11.00000 0.05 0.41 Q15 1 -0.2266 0.6797 0.7315 11.00000 0.05 0.40 Q16 1 0.3357 0.9897 0.4198 11.00000 0.05 0.40 Q17 1 0.1416 0.4839 0.6586 11.00000 0.05 0.40 Q18 1 -0.3425 0.6203 0.3817 11.00000 0.05 0.40 Q19 1 0.3832 0.5204 0.5265 11.00000 0.05 0.40 Q20 1 0.1647 0.5446 0.4983 11.00000 0.05 0.40 REM The information below was added by Olex2. REM REM R1 = 0.0765 for 2879 Fo > 4sig(Fo) and 0.1422 for all 15761 data REM n/a parameters refined using n/a restraints REM Highest difference peak 0.95, deepest hole -0.66 REM Mean Shift 0, Max Shift 0.000. REM +++ Tabular Listing of Refinement Information +++ REM R1_all = 0.1422 REM R1_gt = 0.0765 REM wR_ref = 0.1696 REM GOOF = 1.135 REM Shift_max = 0.000 REM Shift_mean = 0 REM Reflections_all = 15761 REM Reflections_gt = 2879 REM Parameters = n/a REM Hole = -0.66 REM Peak = 0.95 REM Flack = n/a ; _shelx_shelxl_version_number 2014/7 _olex2_submission_special_instructions 'No special instructions were received' loop_ _space_group_symop_operation_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -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 Ni1 Ni 0.11210(8) 0.51300(6) 0.56302(4) 0.01371(19) Uani 1 1 d . . O1 O 0.1798(5) 0.6617(3) 0.6127(2) 0.0171(9) Uani 1 1 d . . O2 O -0.0122(4) 0.6257(3) 0.4953(2) 0.0153(8) Uani 1 1 d . U O3 O -0.2262(4) 0.6164(3) 0.3867(2) 0.0186(9) Uani 1 1 d . . O4 O 0.2329(5) 0.9652(4) 0.3844(2) 0.0252(10) Uani 1 1 d . . O5 O 0.4325(5) 1.1409(4) 0.5270(3) 0.0386(12) Uani 1 1 d . U O6 O 0.2209(5) 1.1597(4) 0.4683(2) 0.0278(11) Uani 1 1 d . . O7 O 0.0163(6) 1.1264(4) 0.3379(2) 0.0302(11) Uani 1 1 d . . O8 O -0.0078(5) 1.0499(4) 0.2370(2) 0.0313(11) Uani 1 1 d . . O9 O -0.0326(4) 0.4894(3) 0.62852(19) 0.0190(8) Uani 1 1 d . . O10 O 0.2599(4) 0.5395(3) 0.50223(19) 0.0166(9) Uani 1 1 d . . N1 N 0.3122(6) 1.1027(4) 0.5064(3) 0.0243(12) Uani 1 1 d . . N2 N -0.0125(5) 1.0418(4) 0.2972(2) 0.0193(11) Uani 1 1 d . . N3 N -0.1078(6) 0.5517(4) 0.7242(3) 0.0213(12) Uani 1 1 d . . N4 N 0.3909(5) 0.4785(4) 0.4245(2) 0.0178(10) Uani 1 1 d . . C1 C 0.1996(6) 0.7624(5) 0.5838(3) 0.0170(12) Uani 1 1 d . . C2 C 0.2959(7) 0.8466(5) 0.6231(3) 0.0207(13) Uani 1 1 d . . H2 H 0.3356 0.8264 0.6681 0.025 Uiso 1 1 calc R . C3 C 0.3309(6) 0.9540(5) 0.5970(3) 0.0203(13) Uani 1 1 d . U H3 H 0.3934 1.0080 0.6238 0.024 Uiso 1 1 calc R . C4 C 0.2738(6) 0.9842(5) 0.5303(3) 0.0187(12) Uani 1 1 d . U C5 C 0.1814(6) 0.9092(5) 0.4905(3) 0.0159(12) Uani 1 1 d . . C6 C 0.1370(6) 0.7977(5) 0.5164(3) 0.0134(11) Uani 1 1 d . U C7 C 0.0271(6) 0.7271(5) 0.4738(3) 0.0150(12) Uani 1 1 d . . C8 C -0.0470(6) 0.7730(5) 0.4093(3) 0.0157(12) Uani 1 1 d . . C9 C 0.0049(7) 0.8806(5) 0.3826(3) 0.0188(13) Uani 1 1 d . . C10 C 0.1450(6) 0.9261(5) 0.4162(3) 0.0163(12) Uani 1 1 d . . C11 C -0.1700(6) 0.7157(5) 0.3702(3) 0.0170(12) Uani 1 1 d . . C12 C -0.2317(7) 0.7718(5) 0.3082(3) 0.0203(13) Uani 1 1 d . . H12 H -0.3136 0.7360 0.2827 0.024 Uiso 1 1 calc R . C13 C -0.1792(7) 0.8730(5) 0.2841(3) 0.0203(13) Uani 1 1 d . . H13 H -0.2219 0.9066 0.2423 0.024 Uiso 1 1 calc R . C14 C -0.0606(7) 0.9267(5) 0.3224(3) 0.0169(12) Uani 1 1 d . . C15 C -0.0602(6) 0.5703(5) 0.6673(3) 0.0201(13) Uani 1 1 d . . H15 H -0.0460 0.6515 0.6549 0.024 Uiso 1 1 calc R . C16 C -0.1420(8) 0.6527(5) 0.7668(3) 0.0281(16) Uani 1 1 d . . H16A H -0.0810 0.6486 0.8108 0.042 Uiso 1 1 calc GR . H16B H -0.2413 0.6471 0.7726 0.042 Uiso 1 1 calc GR . H16C H -0.1263 0.7294 0.7450 0.042 Uiso 1 1 calc GR . C17 C -0.1304(8) 0.4296(5) 0.7481(3) 0.0254(14) Uani 1 1 d . . H17A H -0.2316 0.4169 0.7482 0.038 Uiso 1 1 calc GR . H17B H -0.0781 0.4196 0.7939 0.038 Uiso 1 1 calc GR . H17C H -0.0965 0.3706 0.7183 0.038 Uiso 1 1 calc GR . C18 C 0.3100(6) 0.4579(5) 0.4702(3) 0.0178(12) Uani 1 1 d . . H18 H 0.2885 0.3766 0.4794 0.021 Uiso 1 1 calc R . C19 C 0.4231(7) 0.6030(5) 0.4074(3) 0.0210(13) Uani 1 1 d . . H19A H 0.3539 0.6301 0.3690 0.032 Uiso 1 1 calc GR . H19B H 0.5184 0.6066 0.3959 0.032 Uiso 1 1 calc GR . H19C H 0.4183 0.6555 0.4462 0.032 Uiso 1 1 calc GR . C20 C 0.4475(7) 0.3798(5) 0.3884(3) 0.0231(14) Uani 1 1 d . . H20A H 0.5511 0.3846 0.3956 0.035 Uiso 1 1 calc GR . H20B H 0.4106 0.3864 0.3402 0.035 Uiso 1 1 calc GR . H20C H 0.4186 0.3024 0.4052 0.035 Uiso 1 1 calc GR . 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 Ni1 0.0168(4) 0.0046(3) 0.0197(3) 0.0004(3) 0.0026(3) -0.0019(3) O1 0.023(2) 0.0065(18) 0.022(2) 0.0015(15) 0.0058(18) -0.0031(17) O2 0.018(2) 0.0044(17) 0.0234(19) 0.0019(14) 0.0041(16) -0.0021(15) O3 0.021(2) 0.008(2) 0.026(2) 0.0031(16) 0.0037(19) -0.0019(17) O4 0.029(2) 0.016(2) 0.033(2) 0.0023(18) 0.013(2) -0.0031(19) O5 0.033(3) 0.022(2) 0.057(3) 0.003(2) -0.004(2) -0.018(2) O6 0.036(3) 0.008(2) 0.040(3) 0.0033(19) 0.008(2) 0.002(2) O7 0.048(3) 0.007(2) 0.037(3) -0.0024(18) 0.014(2) -0.001(2) O8 0.043(3) 0.024(2) 0.028(2) 0.0056(19) 0.009(2) -0.006(2) O9 0.023(2) 0.0112(19) 0.024(2) -0.0010(17) 0.0064(17) -0.0021(18) O10 0.019(2) 0.0091(19) 0.023(2) 0.0012(15) 0.0064(17) -0.0018(16) N1 0.032(3) 0.012(2) 0.029(3) -0.001(2) 0.004(3) -0.006(2) N2 0.022(3) 0.011(2) 0.024(3) 0.0048(19) 0.004(2) 0.001(2) N3 0.026(3) 0.011(2) 0.030(3) -0.005(2) 0.013(2) -0.002(2) N4 0.022(2) 0.007(2) 0.025(3) -0.0021(19) 0.007(2) -0.001(2) C1 0.019(3) 0.008(3) 0.025(3) -0.005(2) 0.008(2) -0.002(2) C2 0.024(3) 0.013(3) 0.025(3) -0.001(2) 0.001(3) 0.003(3) C3 0.019(3) 0.008(2) 0.032(3) -0.004(2) -0.002(2) -0.006(2) C4 0.017(2) 0.009(2) 0.029(3) 0.003(2) 0.003(2) -0.005(2) C5 0.014(3) 0.004(2) 0.030(3) -0.003(2) 0.007(3) -0.001(2) C6 0.017(3) 0.005(2) 0.019(2) -0.0030(19) 0.004(2) -0.002(2) C7 0.019(3) 0.005(2) 0.022(3) 0.000(2) 0.008(2) -0.002(2) C8 0.023(3) 0.009(3) 0.017(3) -0.004(2) 0.007(2) -0.004(2) C9 0.030(4) 0.007(3) 0.022(3) -0.002(2) 0.011(3) 0.000(2) C10 0.023(3) 0.005(2) 0.022(3) -0.001(2) 0.007(3) 0.003(2) C11 0.021(3) 0.006(3) 0.025(3) -0.001(2) 0.007(3) 0.005(2) C12 0.026(3) 0.012(3) 0.022(3) -0.001(2) 0.000(3) -0.003(3) C13 0.028(3) 0.011(3) 0.021(3) -0.001(2) 0.000(3) 0.003(3) C14 0.024(3) 0.009(3) 0.019(3) 0.005(2) 0.006(3) 0.002(2) C15 0.024(3) 0.010(3) 0.027(3) 0.004(2) 0.006(3) -0.001(2) C16 0.041(4) 0.009(3) 0.041(4) -0.003(3) 0.024(3) 0.002(3) C17 0.037(4) 0.011(3) 0.029(3) 0.000(2) 0.010(3) -0.006(3) C18 0.020(3) 0.007(3) 0.026(3) 0.001(2) 0.004(3) -0.003(2) C19 0.025(3) 0.013(3) 0.026(3) 0.002(2) 0.008(3) -0.005(3) C20 0.022(3) 0.017(3) 0.032(3) -0.005(3) 0.008(3) 0.001(3) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 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' 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 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 O1 Ni1 O2 170.52(18) . 3_566 O1 Ni1 O2 86.28(17) . . O1 Ni1 O9 88.90(15) . . O1 Ni1 O10 88.97(16) . . O2 Ni1 O2 85.03(14) 3_566 . O2 Ni1 O9 97.07(16) . . O2 Ni1 O9 88.43(15) 3_566 . O3 Ni1 O1 103.77(17) 3_566 . O3 Ni1 O2 169.16(16) 3_566 . O3 Ni1 O2 85.18(16) 3_566 3_566 O3 Ni1 O9 87.31(16) 3_566 . O3 Ni1 O10 91.89(16) 3_566 . O10 Ni1 O2 84.13(16) . . O10 Ni1 O2 93.89(15) . 3_566 O10 Ni1 O9 177.48(16) . . C1 O1 Ni1 123.6(4) . . Ni1 O2 Ni1 94.97(14) 3_566 . C7 O2 Ni1 125.6(4) . . C7 O2 Ni1 126.4(4) . 3_566 C11 O3 Ni1 122.1(4) . 3_566 C15 O9 Ni1 122.6(4) . . C18 O10 Ni1 124.6(3) . . O5 N1 O6 123.9(5) . . O5 N1 C4 118.0(5) . . O6 N1 C4 118.1(5) . . O7 N2 C14 118.2(5) . . O8 N2 O7 123.8(5) . . O8 N2 C14 118.0(5) . . C15 N3 C16 121.7(5) . . C15 N3 C17 121.5(5) . . C17 N3 C16 116.8(5) . . C18 N4 C19 119.8(5) . . C18 N4 C20 121.7(5) . . C19 N4 C20 118.5(4) . . O1 C1 C2 116.0(5) . . O1 C1 C6 126.2(5) . . C6 C1 C2 117.8(5) . . C1 C2 H2 119.2 . . C3 C2 C1 121.7(6) . . C3 C2 H2 119.2 . . C2 C3 H3 120.2 . . C2 C3 C4 119.6(5) . . C4 C3 H3 120.2 . . C3 C4 N1 116.6(5) . . C5 C4 N1 121.6(5) . . C5 C4 C3 121.8(5) . . C4 C5 C6 120.7(5) . . C4 C5 C10 122.2(5) . . C6 C5 C10 116.1(5) . . C1 C6 C7 123.4(5) . . C5 C6 C1 118.3(5) . . C5 C6 C7 118.3(5) . . O2 C7 C6 119.4(5) . . O2 C7 C8 118.5(5) . . C8 C7 C6 121.9(5) . . C9 C8 C7 118.4(5) . . C9 C8 C11 117.5(5) . . C11 C8 C7 124.1(5) . . C8 C9 C10 117.0(5) . . C14 C9 C8 120.5(6) . . C14 C9 C10 121.6(5) . . O4 C10 C5 120.3(6) . . O4 C10 C9 122.0(5) . . C9 C10 C5 117.3(5) . . O3 C11 C8 124.7(5) . . O3 C11 C12 117.7(5) . . C12 C11 C8 117.7(5) . . C11 C12 H12 118.3 . . C13 C12 C11 123.3(6) . . C13 C12 H12 118.3 . . C12 C13 H13 120.9 . . C12 C13 C14 118.2(6) . . C14 C13 H13 120.9 . . C9 C14 N2 120.3(5) . . C9 C14 C13 122.8(5) . . C13 C14 N2 116.8(5) . . O9 C15 N3 124.8(5) . . O9 C15 H15 117.6 . . N3 C15 H15 117.6 . . N3 C16 H16A 109.5 . . N3 C16 H16B 109.5 . . N3 C16 H16C 109.5 . . H16A C16 H16B 109.5 . . H16A C16 H16C 109.5 . . H16B C16 H16C 109.5 . . N3 C17 H17A 109.5 . . N3 C17 H17B 109.5 . . N3 C17 H17C 109.5 . . H17A C17 H17B 109.5 . . H17A C17 H17C 109.5 . . H17B C17 H17C 109.5 . . O10 C18 N4 123.7(5) . . O10 C18 H18 118.2 . . N4 C18 H18 118.2 . . N4 C19 H19A 109.5 . . N4 C19 H19B 109.5 . . N4 C19 H19C 109.5 . . H19A C19 H19B 109.5 . . H19A C19 H19C 109.5 . . H19B C19 H19C 109.5 . . N4 C20 H20A 109.5 . . N4 C20 H20B 109.5 . . N4 C20 H20C 109.5 . . H20A C20 H20B 109.5 . . H20A C20 H20C 109.5 . . H20B C20 H20C 109.5 . . loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 Ni1 O1 1.982(4) . Ni1 O2 2.075(4) . Ni1 O2 2.072(4) 3_566 Ni1 O3 1.979(4) 3_566 Ni1 O9 2.083(4) . Ni1 O10 2.041(4) . O1 C1 1.289(7) . O2 Ni1 2.072(4) 3_566 O2 C7 1.284(6) . O3 Ni1 1.979(4) 3_566 O3 C11 1.293(7) . O4 C10 1.220(7) . O5 N1 1.234(7) . O6 N1 1.239(7) . O7 N2 1.247(6) . O8 N2 1.224(6) . O9 C15 1.247(7) . O10 C18 1.252(6) . N1 C4 1.467(7) . N2 C14 1.475(7) . N3 C15 1.319(7) . N3 C16 1.480(7) . N3 C17 1.465(7) . N4 C18 1.319(7) . N4 C19 1.468(7) . N4 C20 1.468(7) . C1 C2 1.452(8) . C1 C6 1.444(8) . C2 H2 0.9500 . C2 C3 1.366(8) . C3 H3 0.9500 . C3 C4 1.406(8) . C4 C5 1.373(8) . C5 C6 1.435(7) . C5 C10 1.491(8) . C6 C7 1.469(8) . C7 C8 1.465(8) . C8 C9 1.433(8) . C8 C11 1.451(8) . C9 C10 1.488(9) . C9 C14 1.370(8) . C11 C12 1.434(8) . C12 H12 0.9500 . C12 C13 1.353(8) . C13 H13 0.9500 . C13 C14 1.397(9) . C15 H15 0.9500 . C16 H16A 0.9800 . C16 H16B 0.9800 . C16 H16C 0.9800 . C17 H17A 0.9800 . C17 H17B 0.9800 . C17 H17C 0.9800 . C18 H18 0.9500 . C19 H19A 0.9800 . C19 H19B 0.9800 . C19 H19C 0.9800 . C20 H20A 0.9800 . C20 H20B 0.9800 . C20 H20C 0.9800 . 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 Ni1 O1 C1 C2 -157.8(4) . Ni1 O1 C1 C6 21.2(8) . Ni1 O2 C7 C6 -159.0(4) 3_566 Ni1 O2 C7 C6 -27.8(7) . Ni1 O2 C7 C8 25.4(7) 3_566 Ni1 O2 C7 C8 156.6(4) . Ni1 O3 C11 C8 -31.7(7) 3_566 Ni1 O3 C11 C12 146.8(4) 3_566 Ni1 O9 C15 N3 -154.7(5) . Ni1 O10 C18 N4 170.7(4) . O1 C1 C2 C3 176.9(5) . O1 C1 C6 C5 -174.4(5) . O1 C1 C6 C7 7.5(9) . O2 C7 C8 C9 -174.6(5) . O2 C7 C8 C11 5.1(8) . O3 C11 C12 C13 -177.2(5) . O5 N1 C4 C3 35.4(8) . O5 N1 C4 C5 -147.6(6) . O6 N1 C4 C3 -142.7(6) . O6 N1 C4 C5 34.3(8) . O7 N2 C14 C9 -42.6(8) . O7 N2 C14 C13 133.6(6) . O8 N2 C14 C9 139.7(6) . O8 N2 C14 C13 -44.0(7) . N1 C4 C5 C6 -175.3(5) . N1 C4 C5 C10 16.9(8) . C1 C2 C3 C4 -0.6(9) . C1 C6 C7 O2 -3.5(8) . C1 C6 C7 C8 171.9(5) . C2 C1 C6 C5 4.6(8) . C2 C1 C6 C7 -173.5(5) . C2 C3 C4 N1 178.0(5) . C2 C3 C4 C5 1.0(9) . C3 C4 C5 C6 1.5(9) . C3 C4 C5 C10 -166.3(5) . C4 C5 C6 C1 -4.4(8) . C4 C5 C6 C7 173.8(5) . C4 C5 C10 O4 33.3(8) . C4 C5 C10 C9 -153.5(5) . C5 C6 C7 O2 178.4(5) . C5 C6 C7 C8 -6.1(8) . C6 C1 C2 C3 -2.2(8) . C6 C5 C10 O4 -135.0(5) . C6 C5 C10 C9 38.2(7) . C6 C7 C8 C9 10.0(8) . C6 C7 C8 C11 -170.4(5) . C7 C8 C9 C10 10.5(7) . C7 C8 C9 C14 179.8(5) . C7 C8 C11 O3 -1.9(9) . C7 C8 C11 C12 179.6(5) . C8 C9 C10 O4 138.5(5) . C8 C9 C10 C5 -34.5(7) . C8 C9 C14 N2 176.0(5) . C8 C9 C14 C13 0.0(9) . C8 C11 C12 C13 1.4(9) . C9 C8 C11 O3 177.8(5) . C9 C8 C11 C12 -0.8(8) . C10 C5 C6 C1 164.2(5) . C10 C5 C6 C7 -17.7(7) . C10 C9 C14 N2 -15.2(8) . C10 C9 C14 C13 168.8(5) . C11 C8 C9 C10 -169.2(5) . C11 C8 C9 C14 0.1(8) . C11 C12 C13 C14 -1.3(9) . C12 C13 C14 N2 -175.6(5) . C12 C13 C14 C9 0.6(9) . C14 C9 C10 O4 -30.7(8) . C14 C9 C10 C5 156.3(5) . C16 N3 C15 O9 -178.3(6) . C17 N3 C15 O9 1.2(10) . C19 N4 C18 O10 -1.8(9) . C20 N4 C18 O10 179.8(6) .