# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_I _chemical_name_systematic ? _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_sum 'C19 H13 Co Cu N2 O6' _chemical_formula_iupac ? _chemical_formula_weight 487.78 _chemical_absolute_configuration ? _chemical_melting_point ? _space_group_crystal_system orthorhombic _space_group_name_H-M_alt 'C 2 2 21' _space_group_name_Hall 'C 2c 2' loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, -y, z+1/2' '-x, y, -z+1/2' 'x, -y, -z' 'x+1/2, y+1/2, z' '-x+1/2, -y+1/2, z+1/2' '-x+1/2, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 12.3843(6) _cell_length_b 15.8374(7) _cell_length_c 19.3284(10) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 3791.0(3) _cell_formula_units_Z 8 _cell_measurement_reflns_used 7149 _cell_measurement_theta_min 2.3385 _cell_measurement_theta_max 30.4810 _cell_measurement_temperature 103.(2) _exptl_crystal_description block _exptl_crystal_colour red _exptl_crystal_size_max 0.340 _exptl_crystal_size_mid 0.340 _exptl_crystal_size_min 0.200 _exptl_crystal_density_diffrn 1.709 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1960 _exptl_absorpt_coefficient_mu 2.037 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS V2012/1 (Bruker AXS Inc.)' _exptl_absorpt_correction_T_min 0.47 _exptl_absorpt_correction_T_max 0.69 _exptl_special_details ; ; _diffrn_ambient_temperature 103.(2) _diffrn_source ? _diffrn_source_type ? _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean 8.3333 _diffrn_reflns_number 17858 _diffrn_reflns_av_R_equivalents 0.0392 _diffrn_reflns_av_unetI/netI 0.0386 _diffrn_reflns_theta_min 2.09 _diffrn_reflns_theta_max 27.00 _diffrn_reflns_theta_full 27.00 _diffrn_measured_fraction_theta_max 0.998 _diffrn_measured_fraction_theta_full 0.998 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. The pyridine groups bonded to Cu1 is disorder with the occupancy of 0.56 for the carbon atoms. The distance between the Pyridine N and adjacent C was restrained using SADI for the disorder part. The atomic displacement parameters of the disordered atoms were restrained using DELU, SIMU and ISOR. ; _reflns_number_total 4134 _reflns_number_gt 3935 _reflns_threshold_expression >2sigma(I) _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_R_factor_all 0.0309 _refine_ls_R_factor_gt 0.0266 _refine_ls_wR_factor_gt 0.0740 _refine_ls_wR_factor_ref 0.1011 _refine_ls_goodness_of_fit_ref 1.177 _refine_ls_restrained_S_all 1.117 _refine_ls_number_reflns 4134 _refine_ls_number_parameters 356 _refine_ls_number_restraints 490 _refine_ls_hydrogen_treatment constr _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0629P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.529 _refine_diff_density_min -0.530 _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.014(17) _audit_creation_method SHELXL-97 _iucr_refine_instructions_details ; TITL ext2 in C222(1) CELL 0.71073 12.3843 15.8374 19.3284 90.000 90.000 90.000 ZERR 8.00 0.0006 0.0007 0.0010 0.000 0.000 0.000 LATT -7 SYMM -X, -Y, 0.5+Z SYMM -X, Y, 0.5-Z SYMM X, -Y, -Z SFAC C H N O Co Cu UNIT 152 104 16 48 8 8 L.S. 4 BOND $H acta omit -3 54 FMAP 2 PLAN 5 delu 0.02 c13 > n2 simu 0.01 c13 > n2 isor 0.01 c13 > n2 SIZE 0.20 0.34 0.34 TEMP -170 sadi n2 c18 n2 c18a n2 c22 n2 c22a WGHT 0.062900 FVAR 0.04292 0.44119 CU1 6 -0.049926 0.522524 0.420864 11.00000 0.01510 0.02033 = 0.02439 0.00026 -0.00233 0.00191 CO1 5 0.627419 0.564622 0.268247 11.00000 0.00557 0.00876 = 0.01140 0.00008 0.00071 0.00206 C1 1 0.796190 0.490727 0.252784 11.00000 0.00698 0.01551 = 0.01396 -0.00432 0.00092 0.00127 C2 1 0.512108 0.531533 0.373799 11.00000 0.02506 0.01224 = 0.01244 0.00060 0.00436 0.00575 C3 1 0.500000 0.721194 0.250000 10.50000 0.01048 0.00837 = 0.01582 0.00000 0.00110 0.00000 C4 1 0.500000 0.815481 0.250000 10.50000 0.00685 0.01237 = 0.01102 0.00000 0.00096 0.00000 C5 1 0.597319 0.859231 0.250120 11.00000 0.00572 0.01262 = 0.01465 0.00120 -0.00123 0.00099 AFIX 43 H5 2 0.663688 0.829153 0.250370 11.00000 -1.20000 AFIX 0 C6 1 0.597486 0.947446 0.249873 11.00000 0.00750 0.00841 = 0.01157 0.00093 -0.00056 -0.00154 C7 1 0.500000 0.991445 0.250000 10.50000 0.01065 0.01104 = 0.01273 0.00000 0.00000 0.00000 AFIX 43 H7 2 0.500001 1.051430 0.249998 10.50000 -1.20000 AFIX 0 C8 1 0.506587 0.500000 0.500000 10.50000 0.01117 0.01163 = 0.01183 0.00099 0.00000 0.00000 AFIX 43 H8 2 0.583297 0.500002 0.500000 10.50000 -1.20000 AFIX 0 C9 1 0.449750 0.514013 0.438613 11.00000 0.01784 0.00992 = 0.01143 0.00011 0.00011 0.00157 C10 1 0.338770 0.512406 0.438955 11.00000 0.01700 0.01374 = 0.01358 0.00398 -0.00469 0.00047 AFIX 43 H10 2 0.300377 0.519888 0.396847 11.00000 -1.20000 AFIX 0 C11 1 0.282206 0.500000 0.500000 10.50000 0.01106 0.01681 = 0.02097 0.00171 0.00000 0.00000 C12 1 0.160704 0.500000 0.500000 10.50000 0.01416 0.02282 = 0.02496 0.01119 0.00000 0.00000 PART 1 21.00 C13 1 -0.039646 0.336883 0.434208 21.00000 0.02675 0.02322 = 0.02535 -0.00273 -0.00536 0.00631 AFIX 43 H13 2 0.036570 0.343091 0.436479 21.00000 -1.20000 AFIX 0 C14 1 -0.082187 0.255432 0.437430 21.00000 0.03097 0.02136 = 0.03695 -0.00214 -0.00017 0.00302 AFIX 43 H14 2 -0.035012 0.208137 0.438031 21.00000 -1.20000 AFIX 0 C15 1 -0.191146 0.243344 0.439722 21.00000 0.03216 0.02597 = 0.04517 -0.00396 0.00401 -0.00229 AFIX 43 H15 2 -0.220593 0.188104 0.443052 21.00000 -1.20000 AFIX 0 C16 1 -0.257776 0.313287 0.437090 21.00000 0.03288 0.02779 = 0.03723 -0.00312 0.00131 0.00107 AFIX 43 H16 2 -0.333909 0.306856 0.439995 21.00000 -1.20000 AFIX 0 C17 1 -0.213032 0.392013 0.430252 21.00000 0.02844 0.02285 = 0.02774 -0.00263 -0.00384 0.00162 AFIX 43 H17 2 -0.260312 0.439057 0.426769 21.00000 -1.20000 AFIX 0 PART 2 -21.00 same c13 > c17 C13A 1 -0.019138 0.348277 0.431235 -21.00000 0.02953 0.01969 = 0.02349 0.00013 0.00088 0.00439 AFIX 43 H13A 2 0.054509 0.365058 0.431150 -21.00000 -1.20000 AFIX 0 C14A 1 -0.047371 0.262540 0.434602 -21.00000 0.03181 0.02130 = 0.03330 -0.00262 0.00182 0.00220 AFIX 43 H14A 2 0.007132 0.220601 0.438520 -21.00000 -1.20000 AFIX 0 C15A 1 -0.154001 0.239712 0.432202 -21.00000 0.03659 0.02019 = 0.04638 -0.00202 0.00514 -0.00010 AFIX 43 H15A 2 -0.174308 0.181930 0.434404 -21.00000 -1.20000 AFIX 0 C16A 1 -0.231755 0.302222 0.426515 -21.00000 0.03080 0.02295 = 0.03892 -0.00280 0.00349 -0.00140 AFIX 43 H16A 2 -0.306186 0.287957 0.424333 -21.00000 -1.20000 AFIX 0 C17A 1 -0.199477 0.385228 0.424078 -21.00000 0.02981 0.02115 = 0.02602 -0.00421 -0.00203 0.00365 AFIX 43 H17A 2 -0.252899 0.427870 0.419252 -21.00000 -1.20000 AFIX 0 PART 1 21.00 C18 1 0.017231 0.675322 0.362097 21.00000 0.02161 0.02383 = 0.02232 0.00365 -0.00222 -0.00003 AFIX 43 H18 2 0.082966 0.644514 0.359965 21.00000 -1.20000 AFIX 0 C19 1 0.015376 0.758604 0.337669 21.00000 0.02204 0.02548 = 0.02512 0.00160 -0.00175 0.00722 AFIX 43 H19 2 0.079747 0.784988 0.321944 21.00000 -1.20000 AFIX 0 C20 1 -0.080651 0.801315 0.336827 21.00000 0.02316 0.02418 = 0.02904 0.00451 0.00037 0.00054 AFIX 43 H20 2 -0.083792 0.857398 0.319508 21.00000 -1.20000 AFIX 0 C21 1 -0.170008 0.763821 0.360468 21.00000 0.02494 0.02473 = 0.02628 0.00001 -0.00605 0.00444 AFIX 43 H21 2 -0.236895 0.793184 0.359961 21.00000 -1.20000 AFIX 0 C22 1 -0.164812 0.680534 0.386183 21.00000 0.02270 0.02117 = 0.02194 -0.00118 -0.00960 -0.00041 AFIX 43 H22 2 -0.229077 0.654274 0.402224 21.00000 -1.20000 AFIX 0 PART 2 -21.00 same c18 > c22 C18A 1 0.009956 0.687015 0.366472 -21.00000 0.02050 0.02225 = 0.02335 0.00039 -0.00335 -0.00006 AFIX 43 H18A 2 0.081721 0.665904 0.367964 -21.00000 -1.20000 AFIX 0 C19A 1 -0.007907 0.768763 0.341346 -21.00000 0.02562 0.02867 = 0.02903 0.00482 -0.00068 0.00094 AFIX 43 H19A 2 0.050059 0.801554 0.323614 -21.00000 -1.20000 AFIX 0 C20A 1 -0.110412 0.800267 0.342899 -21.00000 0.02231 0.02362 = 0.02645 0.00556 -0.00319 0.00374 AFIX 43 H20A 2 -0.124120 0.855903 0.326761 -21.00000 -1.20000 AFIX 0 C21A 1 -0.192687 0.752509 0.367364 -21.00000 0.01993 0.01921 = 0.02464 0.00354 -0.00454 0.00278 AFIX 43 H21A 2 -0.263884 0.774729 0.369175 -21.00000 -1.20000 AFIX 0 C22A 1 -0.171787 0.669578 0.390112 -21.00000 0.02225 0.02059 = 0.02144 -0.00256 -0.01055 0.00113 AFIX 43 H22A 2 -0.229657 0.635882 0.406803 -21.00000 -1.20000 AFIX 0 PART 0 N1 3 -0.099962 0.407341 0.428072 11.00000 0.02996 0.01769 = 0.01777 -0.00111 -0.00392 0.00457 N2 3 -0.071406 0.637275 0.388622 11.00000 0.02054 0.01769 = 0.02117 -0.00314 -0.00864 0.00066 O1 4 0.790473 0.570657 0.246461 11.00000 0.00680 0.00845 = 0.02922 -0.00033 0.00081 0.00196 O2 4 0.711609 0.448260 0.262650 11.00000 0.00681 0.01248 = 0.03730 0.00069 0.00328 0.00073 O3 4 0.611778 0.544772 0.376425 11.00000 0.01887 0.02445 = 0.01935 0.00601 0.00547 0.00085 O4 4 0.462594 0.531698 0.317688 11.00000 0.02993 0.02830 = 0.01179 0.00318 -0.00082 0.00016 O5 4 0.587743 0.685728 0.265074 11.00000 0.00642 0.01072 = 0.03164 0.00388 -0.00152 0.00157 O6 4 0.114910 0.523890 0.445567 11.00000 0.00792 0.05677 = 0.03762 0.02103 -0.00267 0.00049 HKLF 4 REM ext2 in C222(1) REM R1 = 0.0266 for 3935 Fo > 4sig(Fo) and 0.0309 for all 4134 data REM 356 parameters refined using 490 restraints END WGHT 0.0613 0.0000 REM Highest difference peak 0.529, deepest hole -0.530, 1-sigma level 0.134 Q1 1 0.3078 0.5177 0.5297 11.00000 0.05 0.53 Q2 1 0.3124 0.5264 0.4742 11.00000 0.05 0.52 Q3 1 0.2441 0.5000 0.5000 10.50000 0.05 0.46 Q4 1 0.3982 0.5254 0.4507 11.00000 0.05 0.43 Q5 1 0.4725 0.5184 0.4597 11.00000 0.05 0.41 ; 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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Co Co 0.3494 0.9721 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _computing_data_collection 'Bruker Apex2' _computing_cell_refinement 'SAINT V8.27B (Bruker AXS Inc., 2012)' _computing_data_reduction 'SAINT V8.27B (Bruker AXS Inc., 2012)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker Apex2' _computing_publication_material 'Bruker Apex2' loop_ _atom_site_type_symbol _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_disorder_assembly _atom_site_disorder_group Cu Cu1 -0.04993(4) 0.52252(3) 0.42086(2) 0.01994(13) Uani d . 1.0 A . Co Co1 0.62742(3) 0.56462(2) 0.26825(2) 0.00858(11) Uani d . 1.0 . . C C1 0.7962(3) 0.4907(2) 0.25278(16) 0.0122(6) Uani d . 1.0 . . C C2 0.5121(3) 0.5315(2) 0.37380(18) 0.0166(7) Uani d . 1.0 . . C C3 0.5 0.7212(3) 0.25 0.0116(9) Uani d S 1.0 . . C C4 0.5 0.8155(3) 0.25 0.0101(9) Uani d S 1.0 . . C C5 0.5973(3) 0.8592(2) 0.25012(17) 0.0110(6) Uani d . 1.0 . . H H5 0.6637 0.8292 0.2504 0.013 Uiso calc R 1.0 . . C C6 0.5975(3) 0.94745(18) 0.24987(16) 0.0092(6) Uani d . 1.0 . . C C7 0.5 0.9914(3) 0.25 0.0115(9) Uani d S 1.0 . . H H7 0.5 1.0514 0.25 0.014 Uiso calc SR 1.0 . . C C8 0.5066(4) 0.5 0.5 0.0115(9) Uani d S 1.0 . . H H8 0.5833 0.5 0.5 0.014 Uiso calc SR 1.0 . . C C9 0.4497(3) 0.51401(19) 0.43861(16) 0.0131(7) Uani d . 1.0 . . C C10 0.3388(3) 0.5124(2) 0.43895(17) 0.0148(7) Uani d . 1.0 . . H H10 0.3004 0.5199 0.3968 0.018 Uiso calc R 1.0 . . C C11 0.2822(4) 0.5 0.5 0.0163(10) Uani d S 1.0 . . C C12 0.1607(4) 0.5 0.5 0.0206(11) Uani d S 1.0 . . C C13 -0.0396(15) 0.3369(11) 0.4342(14) 0.025(2) Uani d PDU 0.44(3) A 1 H H13 0.0366 0.3431 0.4365 0.03 Uiso calc PR 0.44(3) A 1 C C14 -0.0822(17) 0.2554(10) 0.4374(10) 0.030(2) Uani d PDU 0.44(3) A 1 H H14 -0.035 0.2081 0.438 0.036 Uiso calc PR 0.44(3) A 1 C C15 -0.1911(17) 0.2433(9) 0.4397(9) 0.034(2) Uani d PDU 0.44(3) A 1 H H15 -0.2206 0.1881 0.4431 0.041 Uiso calc PR 0.44(3) A 1 C C16 -0.2578(15) 0.3133(11) 0.4371(10) 0.033(2) Uani d PDU 0.44(3) A 1 H H16 -0.3339 0.3069 0.44 0.039 Uiso calc PR 0.44(3) A 1 C C17 -0.2130(17) 0.3920(11) 0.4303(16) 0.026(2) Uani d PDU 0.44(3) A 1 H H17 -0.2603 0.4391 0.4268 0.032 Uiso calc PR 0.44(3) A 1 C C13A -0.0191(12) 0.3483(8) 0.4312(10) 0.024(2) Uani d PDU 0.56(3) A 2 H H13A 0.0545 0.3651 0.4311 0.029 Uiso calc PR 0.56(3) A 2 C C14A -0.0474(14) 0.2625(7) 0.4346(7) 0.029(2) Uani d PDU 0.56(3) A 2 H H14A 0.0071 0.2206 0.4385 0.035 Uiso calc PR 0.56(3) A 2 C C15A -0.1540(15) 0.2397(7) 0.4322(7) 0.034(2) Uani d PDU 0.56(3) A 2 H H15A -0.1743 0.1819 0.4344 0.041 Uiso calc PR 0.56(3) A 2 C C16A -0.2318(12) 0.3022(8) 0.4265(8) 0.031(2) Uani d PDU 0.56(3) A 2 H H16A -0.3062 0.288 0.4243 0.037 Uiso calc PR 0.56(3) A 2 C C17A -0.1995(13) 0.3852(9) 0.4241(12) 0.026(2) Uani d PDU 0.56(3) A 2 H H17A -0.2529 0.4279 0.4193 0.031 Uiso calc PR 0.56(3) A 2 C C18 0.0172(12) 0.6753(11) 0.3621(15) 0.023(2) Uani d PDU 0.44(3) A 1 H H18 0.083 0.6445 0.36 0.027 Uiso calc PR 0.44(3) A 1 C C19 0.0154(14) 0.7586(11) 0.3377(11) 0.024(2) Uani d PDU 0.44(3) A 1 H H19 0.0797 0.785 0.3219 0.029 Uiso calc PR 0.44(3) A 1 C C20 -0.0807(16) 0.8013(10) 0.3368(10) 0.025(2) Uani d PDU 0.44(3) A 1 H H20 -0.0838 0.8574 0.3195 0.031 Uiso calc PR 0.44(3) A 1 C C21 -0.1700(14) 0.7638(11) 0.3605(11) 0.025(2) Uani d PDU 0.44(3) A 1 H H21 -0.2369 0.7932 0.36 0.03 Uiso calc PR 0.44(3) A 1 C C22 -0.1648(11) 0.6805(12) 0.3862(18) 0.022(2) Uani d PDU 0.44(3) A 1 H H22 -0.2291 0.6543 0.4022 0.026 Uiso calc PR 0.44(3) A 1 C C18A 0.0100(10) 0.6870(8) 0.3665(11) 0.022(2) Uani d PDU 0.56(3) A 2 H H18A 0.0817 0.6659 0.368 0.026 Uiso calc PR 0.56(3) A 2 C C19A -0.0079(12) 0.7688(9) 0.3413(9) 0.028(2) Uani d PDU 0.56(3) A 2 H H19A 0.0501 0.8016 0.3236 0.033 Uiso calc PR 0.56(3) A 2 C C20A -0.1104(12) 0.8003(8) 0.3429(8) 0.0241(19) Uani d PDU 0.56(3) A 2 H H20A -0.1241 0.8559 0.3268 0.029 Uiso calc PR 0.56(3) A 2 C C21A -0.1927(11) 0.7525(8) 0.3674(8) 0.0213(18) Uani d PDU 0.56(3) A 2 H H21A -0.2639 0.7747 0.3692 0.026 Uiso calc PR 0.56(3) A 2 C C22A -0.1718(9) 0.6696(10) 0.3901(14) 0.0214(19) Uani d PDU 0.56(3) A 2 H H22A -0.2297 0.6359 0.4068 0.026 Uiso calc PR 0.56(3) A 2 N N1 -0.1000(3) 0.40734(18) 0.42807(17) 0.0218(7) Uani d U 1.0 . . N N2 -0.0714(3) 0.63727(18) 0.38862(16) 0.0198(6) Uani d DU 1.0 . . O O1 0.79047(19) 0.57066(14) 0.24646(13) 0.0148(5) Uani d . 1.0 . . O O2 0.71161(19) 0.44826(14) 0.26265(14) 0.0189(5) Uani d . 1.0 . . O O3 0.6118(2) 0.54477(15) 0.37642(13) 0.0209(6) Uani d . 1.0 . . O O4 0.4626(2) 0.53170(17) 0.31769(13) 0.0233(6) Uani d . 1.0 . . O O5 0.58774(19) 0.68573(14) 0.26507(14) 0.0163(5) Uani d . 1.0 . . O O6 0.1149(2) 0.5239(2) 0.44557(15) 0.0341(7) Uani d . 1.0 . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 Cu1 0.0151(2) 0.0203(2) 0.0244(2) 0.00191(19) -0.00233(19) 0.00026(18) Co1 0.0056(2) 0.00876(19) 0.0114(2) 0.00206(17) 0.00071(18) 0.00008(16) C1 0.0070(14) 0.0155(15) 0.0140(16) 0.0013(13) 0.0009(12) -0.0043(12) C2 0.0251(19) 0.0122(14) 0.0124(16) 0.0057(14) 0.0044(14) 0.0006(13) C3 0.010(2) 0.008(2) 0.016(2) 0 0.0011(18) 0 C4 0.007(2) 0.012(2) 0.011(2) 0 0.0010(17) 0 C5 0.0057(15) 0.0126(14) 0.0147(16) 0.0010(12) -0.0012(12) 0.0012(12) C6 0.0075(14) 0.0084(13) 0.0116(14) -0.0015(11) -0.0006(11) 0.0009(11) C7 0.011(2) 0.011(2) 0.013(2) 0 0.0000(17) 0 C8 0.011(2) 0.012(2) 0.012(2) 0 0 0.0010(17) C9 0.0178(17) 0.0099(14) 0.0114(15) 0.0016(14) 0.0001(13) 0.0001(11) C10 0.0170(17) 0.0137(15) 0.0136(16) 0.0005(13) -0.0047(13) 0.0040(12) C11 0.011(2) 0.017(2) 0.021(2) 0 0 0.0017(18) C12 0.014(2) 0.023(3) 0.025(3) 0 0 0.011(2) C13 0.027(4) 0.023(4) 0.025(4) 0.006(4) -0.005(4) -0.003(4) C14 0.031(5) 0.021(3) 0.037(4) 0.003(4) 0.000(4) -0.002(3) C15 0.032(5) 0.026(4) 0.045(4) -0.002(4) 0.004(4) -0.004(3) C16 0.033(5) 0.028(4) 0.037(4) 0.001(4) 0.001(4) -0.003(4) C17 0.028(4) 0.023(4) 0.028(4) 0.002(4) -0.004(4) -0.003(4) C13A 0.030(4) 0.020(3) 0.023(3) 0.004(3) 0.001(4) 0.000(3) C14A 0.032(4) 0.021(3) 0.033(3) 0.002(4) 0.002(4) -0.003(3) C15A 0.037(5) 0.020(3) 0.046(4) 0.000(4) 0.005(4) -0.002(3) C16A 0.031(4) 0.023(3) 0.039(4) -0.001(3) 0.003(3) -0.003(3) C17A 0.030(4) 0.021(3) 0.026(4) 0.004(3) -0.002(4) -0.004(3) C18 0.022(4) 0.024(4) 0.022(4) 0.000(3) -0.002(3) 0.004(4) C19 0.022(4) 0.025(4) 0.025(3) 0.007(3) -0.002(4) 0.002(3) C20 0.023(5) 0.024(3) 0.029(4) 0.001(4) 0.000(4) 0.005(3) C21 0.025(4) 0.025(4) 0.026(4) 0.004(4) -0.006(4) 0.000(3) C22 0.023(4) 0.021(4) 0.022(4) 0.000(3) -0.010(3) -0.001(4) C18A 0.021(3) 0.022(4) 0.023(4) 0.000(3) -0.003(3) 0.000(3) C19A 0.026(4) 0.029(3) 0.029(3) 0.001(3) -0.001(4) 0.005(3) C20A 0.022(4) 0.024(3) 0.026(3) 0.004(3) -0.003(4) 0.006(3) C21A 0.020(4) 0.019(3) 0.025(3) 0.003(3) -0.005(3) 0.004(3) C22A 0.022(3) 0.021(4) 0.021(4) 0.001(3) -0.011(3) -0.003(3) N1 0.0300(17) 0.0177(13) 0.0178(14) 0.0046(13) -0.0039(13) -0.0011(11) N2 0.0205(16) 0.0177(13) 0.0212(15) 0.0007(12) -0.0086(13) -0.0031(12) O1 0.0068(10) 0.0084(10) 0.0292(13) 0.0020(9) 0.0008(10) -0.0003(9) O2 0.0068(11) 0.0125(11) 0.0373(15) 0.0007(9) 0.0033(12) 0.0007(10) O3 0.0189(14) 0.0244(13) 0.0193(13) 0.0009(11) 0.0055(11) 0.0060(10) O4 0.0299(15) 0.0283(13) 0.0118(11) 0.0002(12) -0.0008(12) 0.0032(10) O5 0.0064(11) 0.0107(10) 0.0316(14) 0.0016(9) -0.0015(12) 0.0039(10) O6 0.0079(13) 0.0568(18) 0.0376(17) 0.0005(14) -0.0027(12) 0.0210(15) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag Cu1 N1 . 1.932(3) ? Cu1 N2 . 1.940(3) ? Cu1 O6 . 2.097(3) ? Co1 O5 . 1.981(2) ? Co1 O1 . 2.065(2) ? Co1 O4 3_655 2.067(3) ? Co1 O2 . 2.120(2) ? Co1 O3 . 2.123(3) ? Co1 O4 . 2.313(3) ? Co1 C1 . 2.414(3) ? C1 O2 . 1.259(4) ? C1 O1 . 1.274(4) ? C1 C6 7_645 1.485(4) ? C2 O4 . 1.246(4) ? C2 O3 . 1.253(5) ? C2 C9 . 1.498(5) ? C3 O5 . 1.257(3) ? C3 O5 3_655 1.257(3) ? C3 C4 . 1.493(6) ? C4 C5 . 1.390(4) ? C4 C5 3_655 1.390(4) ? C5 C6 . 1.397(4) ? C5 H5 . 0.95 ? C6 C7 . 1.394(4) ? C6 C1 7_655 1.485(4) ? C7 C6 3_655 1.394(4) ? C7 H7 . 0.95 ? C8 C9 4_566 1.397(4) ? C8 C9 . 1.397(4) ? C8 H8 . 0.95 ? C9 C10 . 1.375(5) ? C10 C11 . 1.386(4) ? C10 H10 . 0.95 ? C11 C10 4_566 1.386(4) ? C11 C12 . 1.505(7) ? C12 O6 . 1.254(4) ? C12 O6 4_566 1.254(4) ? C13 N1 . 1.348(18) ? C13 C14 . 1.395(13) ? C13 H13 . 0.95 ? C14 C15 . 1.364(14) ? C14 H14 . 0.95 ? C15 C16 . 1.382(13) ? C15 H15 . 0.95 ? C16 C17 . 1.371(12) ? C16 H16 . 0.95 ? C17 N1 . 1.42(2) ? C17 H17 . 0.95 ? C13A N1 . 1.371(14) ? C13A C14A . 1.404(11) ? C13A H13A . 0.95 ? C14A C15A . 1.370(12) ? C14A H14A . 0.95 ? C15A C16A . 1.385(12) ? C15A H15A . 0.95 ? C16A C17A . 1.375(10) ? C16A H16A . 0.95 ? C17A N1 . 1.284(17) ? C17A H17A . 0.95 ? C18 N2 . 1.353(11) ? C18 C19 . 1.401(12) ? C18 H18 . 0.95 ? C19 C20 . 1.368(12) ? C19 H19 . 0.95 ? C20 C21 . 1.336(13) ? C20 H20 . 0.95 ? C21 C22 . 1.411(12) ? C21 H21 . 0.95 ? C22 N2 . 1.345(11) ? C22 H22 . 0.95 ? C18A N2 . 1.349(9) ? C18A C19A . 1.400(10) ? C18A H18A . 0.95 ? C19A C20A . 1.364(10) ? C19A H19A . 0.95 ? C20A C21A . 1.354(10) ? C20A H20A . 0.95 ? C21A C22A . 1.409(10) ? C21A H21A . 0.95 ? C22A N2 . 1.345(9) ? C22A H22A . 0.95 ? O4 Co1 3_655 2.067(3) ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag N1 Cu1 N2 . . 149.78(13) ? N1 Cu1 O6 . . 107.80(14) ? N2 Cu1 O6 . . 101.36(13) ? O5 Co1 O1 . . 101.04(9) ? O5 Co1 O4 . 3_655 94.91(10) ? O1 Co1 O4 . 3_655 112.03(11) ? O5 Co1 O2 . . 164.16(10) ? O1 Co1 O2 . . 63.19(9) ? O4 Co1 O2 3_655 . 90.28(11) ? O5 Co1 O3 . . 98.70(10) ? O1 Co1 O3 . . 107.27(10) ? O4 Co1 O3 3_655 . 134.81(11) ? O2 Co1 O3 . . 88.08(10) ? O5 Co1 O4 . . 90.70(10) ? O1 Co1 O4 . . 163.24(9) ? O4 Co1 O4 3_655 . 78.42(11) ? O2 Co1 O4 . . 105.02(9) ? O3 Co1 O4 . . 58.62(10) ? O5 Co1 C1 . . 132.87(10) ? O1 Co1 C1 . . 31.84(10) ? O4 Co1 C1 3_655 . 104.19(11) ? O2 Co1 C1 . . 31.40(10) ? O3 Co1 C1 . . 97.42(10) ? O4 Co1 C1 . . 134.90(10) ? O2 C1 O1 . . 119.9(3) ? O2 C1 C6 . 7_645 119.7(3) ? O1 C1 C6 . 7_645 120.3(3) ? O2 C1 Co1 . . 61.31(16) ? O1 C1 Co1 . . 58.80(17) ? C6 C1 Co1 7_645 . 174.6(2) ? O4 C2 O3 . . 121.3(3) ? O4 C2 C9 . . 118.3(3) ? O3 C2 C9 . . 120.3(3) ? O5 C3 O5 . 3_655 126.9(4) ? O5 C3 C4 . . 116.5(2) ? O5 C3 C4 3_655 . 116.5(2) ? C5 C4 C5 . 3_655 120.2(4) ? C5 C4 C3 . . 119.9(2) ? C5 C4 C3 3_655 . 119.9(2) ? C4 C5 C6 . . 120.0(3) ? C4 C5 H5 . . 120.0 ? C6 C5 H5 . . 120.0 ? C7 C6 C5 . . 119.9(3) ? C7 C6 C1 . 7_655 122.5(3) ? C5 C6 C1 . 7_655 117.6(3) ? C6 C7 C6 . 3_655 120.0(4) ? C6 C7 H7 . . 120.0 ? C6 C7 H7 3_655 . 120.0 ? C9 C8 C9 4_566 . 119.5(5) ? C9 C8 H8 4_566 . 120.2 ? C9 C8 H8 . . 120.2 ? C10 C9 C8 . . 119.8(3) ? C10 C9 C2 . . 121.5(3) ? C8 C9 C2 . . 118.7(4) ? C9 C10 C11 . . 120.8(3) ? C9 C10 H10 . . 119.6 ? C11 C10 H10 . . 119.6 ? C10 C11 C10 4_566 . 119.3(5) ? C10 C11 C12 4_566 . 120.4(2) ? C10 C11 C12 . . 120.4(2) ? O6 C12 O6 . 4_566 126.2(5) ? O6 C12 C11 . . 116.9(3) ? O6 C12 C11 4_566 . 116.9(3) ? N1 C13 C14 . . 124.1(13) ? N1 C13 H13 . . 118.0 ? C14 C13 H13 . . 118.0 ? C15 C14 C13 . . 120.3(12) ? C15 C14 H14 . . 119.8 ? C13 C14 H14 . . 119.8 ? C14 C15 C16 . . 118.5(11) ? C14 C15 H15 . . 120.8 ? C16 C15 H15 . . 120.8 ? C17 C16 C15 . . 119.4(12) ? C17 C16 H16 . . 120.3 ? C15 C16 H16 . . 120.3 ? C16 C17 N1 . . 123.8(13) ? C16 C17 H17 . . 118.1 ? N1 C17 H17 . . 118.1 ? N1 C13A C14A . . 118.7(9) ? N1 C13A H13A . . 120.7 ? C14A C13A H13A . . 120.7 ? C15A C14A C13A . . 119.6(9) ? C15A C14A H14A . . 120.2 ? C13A C14A H14A . . 120.2 ? C14A C15A C16A . . 119.0(9) ? C14A C15A H15A . . 120.5 ? C16A C15A H15A . . 120.5 ? C17A C16A C15A . . 118.9(10) ? C17A C16A H16A . . 120.5 ? C15A C16A H16A . . 120.5 ? N1 C17A C16A . . 122.5(11) ? N1 C17A H17A . . 118.7 ? C16A C17A H17A . . 118.7 ? N2 C18 C19 . . 122.2(13) ? N2 C18 H18 . . 118.9 ? C19 C18 H18 . . 118.9 ? C20 C19 C18 . . 118.9(13) ? C20 C19 H19 . . 120.5 ? C18 C19 H19 . . 120.5 ? C21 C20 C19 . . 119.7(12) ? C21 C20 H20 . . 120.1 ? C19 C20 H20 . . 120.1 ? C20 C21 C22 . . 119.9(13) ? C20 C21 H21 . . 120.1 ? C22 C21 H21 . . 120.1 ? N2 C22 C21 . . 121.8(13) ? N2 C22 H22 . . 119.1 ? C21 C22 H22 . . 119.1 ? N2 C18A C19A . . 122.1(11) ? N2 C18A H18A . . 118.9 ? C19A C18A H18A . . 118.9 ? C20A C19A C18A . . 118.5(10) ? C20A C19A H19A . . 120.7 ? C18A C19A H19A . . 120.7 ? C21A C20A C19A . . 120.2(9) ? C21A C20A H20A . . 119.9 ? C19A C20A H20A . . 119.9 ? C20A C21A C22A . . 119.4(9) ? C20A C21A H21A . . 120.3 ? C22A C21A H21A . . 120.3 ? N2 C22A C21A . . 121.2(10) ? N2 C22A H22A . . 119.4 ? C21A C22A H22A . . 119.4 ? C17A N1 C13 . . 108.1(9) ? C17A N1 C13A . . 121.2(8) ? C13 N1 C13A . . 13.3(9) ? C17A N1 C17 . . 7.9(18) ? C13 N1 C17 . . 113.7(10) ? C13A N1 C17 . . 126.9(9) ? C17A N1 Cu1 . . 124.2(7) ? C13 N1 Cu1 . . 127.6(8) ? C13A N1 Cu1 . . 114.4(6) ? C17 N1 Cu1 . . 118.6(7) ? C22A N2 C22 . . 8.9(12) ? C22A N2 C18A . . 118.4(8) ? C22 N2 C18A . . 109.5(9) ? C22A N2 C18 . . 126.1(9) ? C22 N2 C18 . . 117.2(11) ? C18A N2 C18 . . 9.5(15) ? C22A N2 Cu1 . . 118.5(6) ? C22 N2 Cu1 . . 127.3(8) ? C18A N2 Cu1 . . 123.1(6) ? C18 N2 Cu1 . . 115.3(8) ? C1 O1 Co1 . . 89.4(2) ? C1 O2 Co1 . . 87.28(18) ? C2 O3 Co1 . . 94.3(2) ? C2 O4 Co1 . 3_655 164.9(3) ? C2 O4 Co1 . . 85.7(2) ? Co1 O4 Co1 3_655 . 94.99(10) ? C3 O5 Co1 . . 130.8(2) ? C12 O6 Cu1 . . 128.9(3) ? _database_code_depnum_ccdc_archive 'CCDC 932108' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_NTU-Z7c _iucr_refine_instructions_details ; TITL NTU-Z7c in C222(1) CELL 0.71073 12.4188 15.5787 19.6801 90.000 90.000 90.000 ZERR 8.00 0.0025 0.0031 0.0039 0.000 0.000 0.000 LATT -7 SYMM -X, -Y, 0.5+Z SYMM -X, Y, 0.5-Z SYMM X, -Y, -Z SFAC C H N O Ni CU UNIT 152 34 16 48 8 8 acta 50 isor 0.01 o1 c15 c8 c9 c7 isor 0.001 o2 o6 simu 0.005 0.01 3.8 o2 o6 DFIX 1.50 0.01 C15 C17 L.S. 12 BOND FMAP 2 PLAN -10 WGHT 0.120000 FVAR 0.05415 CU1 6 0.959374 0.021994 0.419965 11.00000 0.06525 0.06192 = 0.09031 0.01051 -0.00255 0.00698 NI1 5 1.627825 0.059141 0.266354 11.00000 0.02579 0.02565 = 0.04120 0.00132 0.00316 0.00523 N1 3 0.938878 0.138371 0.386281 11.00000 0.06997 0.05197 = 0.06587 -0.00797 -0.01861 0.00813 N2 3 0.904084 -0.093950 0.429635 11.00000 0.08442 0.05603 = 0.05410 0.00002 -0.00826 0.01651 O1 4 1.124063 0.020032 0.446286 11.00000 0.09119 0.14987 = 0.17623 0.05797 -0.01237 -0.01083 O2 4 1.619227 0.053313 0.385907 11.00000 0.10082 O3 4 1.791916 0.070158 0.240226 11.00000 0.05667 0.02997 = 0.08532 0.00441 0.01912 0.01489 O4 4 1.712149 -0.048801 0.267417 11.00000 0.03882 0.03794 = 0.09450 0.01371 0.01474 0.00611 O5 4 1.590099 0.178671 0.258377 11.00000 0.03807 0.02678 = 0.07424 -0.00459 -0.00499 0.00235 O6 4 1.488015 0.023754 0.320652 11.00000 0.08698 C1 1 0.842629 0.174617 0.384996 11.00000 0.06821 0.07109 = 0.07981 -0.01448 -0.02526 0.01643 AFIX 43 H1A 2 0.783994 0.142452 0.399686 11.00000 -1.20000 AFIX 0 C2 1 0.824080 0.258325 0.362866 11.00000 0.13416 0.08472 = 0.10540 -0.01645 -0.04062 0.05345 AFIX 43 H2A 2 0.755688 0.282611 0.363852 11.00000 -1.20000 AFIX 0 C3 1 0.912835 0.303645 0.339273 11.00000 0.17700 0.07397 = 0.07685 0.00700 -0.03385 0.00840 AFIX 43 H3A 2 0.904700 0.359766 0.324005 11.00000 -1.20000 AFIX 0 C4 1 1.012243 0.265771 0.338480 11.00000 0.16664 0.09315 = 0.07363 0.00975 0.00551 -0.02613 AFIX 43 H4A 2 1.071860 0.294544 0.321187 11.00000 -1.20000 AFIX 0 C5 1 1.021479 0.183370 0.364171 11.00000 0.09315 0.07460 = 0.06908 -0.00017 -0.00710 -0.02068 AFIX 43 H5A 2 1.089522 0.158534 0.365897 11.00000 -1.20000 AFIX 0 C6 1 0.800363 -0.109265 0.431689 11.00000 0.07819 0.07464 = 0.09757 -0.00149 -0.01854 -0.01133 AFIX 43 H6A 2 0.753341 -0.062958 0.428699 11.00000 -1.20000 AFIX 0 C7 1 0.757734 -0.189690 0.437991 11.00000 0.13885 0.11540 = 0.12966 0.00555 -0.01838 -0.01069 AFIX 43 H7A 2 0.683842 -0.199007 0.440123 11.00000 -1.20000 AFIX 0 C8 1 0.831581 -0.256989 0.441038 11.00000 0.14277 0.08542 = 0.13440 -0.00211 0.00094 -0.00984 AFIX 43 H8A 2 0.806125 -0.312855 0.445438 11.00000 -1.20000 AFIX 0 C9 1 0.940199 -0.243465 0.437763 11.00000 0.14238 0.08231 = 0.12089 -0.01428 -0.00134 0.01700 AFIX 43 H9A 2 0.989493 -0.288360 0.439352 11.00000 -1.20000 AFIX 0 C10 1 0.972516 -0.157593 0.431857 11.00000 0.14043 0.06914 = 0.06465 0.00309 -0.00959 0.03370 AFIX 43 H10A 2 1.045723 -0.145402 0.429418 11.00000 -1.20000 AFIX 0 C11 1 1.168149 0.000000 0.500000 10.50000 0.03629 0.11361 = 0.22442 0.12475 0.00000 0.00000 C12 1 1.288935 0.000000 0.500000 10.50000 0.04628 0.04978 = 0.09734 0.02531 0.00000 0.00000 C13 1 1.344742 0.012160 0.440392 11.00000 0.08223 0.05199 = 0.05580 0.01506 -0.03116 -0.00886 AFIX 43 H13A 2 1.306681 0.018905 0.400047 11.00000 -1.20000 AFIX 0 C15 1 1.526708 0.031645 0.376646 11.00000 0.12433 0.04726 = 0.04718 -0.01030 -0.01022 0.01126 C17 1 1.455060 0.014583 0.438981 11.00000 0.06952 0.04748 = 0.02487 0.00329 -0.00412 -0.00185 C18 1 1.511459 0.000000 0.500000 10.50000 0.05525 0.04582 = 0.03820 0.00073 0.00000 0.00000 AFIX 43 H18A 2 1.586345 0.000000 0.500000 10.50000 -1.20000 AFIX 0 C19 1 1.798183 -0.007939 0.253414 11.00000 0.04799 0.03051 = 0.05295 0.00154 -0.00019 0.01314 C21 1 1.902942 -0.144386 0.250852 11.00000 0.02441 0.03741 = 0.04425 -0.00435 0.00285 -0.00382 AFIX 43 H21A 2 1.837845 -0.173880 0.251628 11.00000 -1.20000 AFIX 0 C22 1 1.903516 -0.054564 0.250540 11.00000 0.03526 0.03130 = 0.04403 0.00031 0.00533 0.00256 C23 1 2.000000 -0.010785 0.250000 10.50000 0.04663 0.02687 = 0.04458 0.00000 0.01345 0.00000 AFIX 43 H23A 2 2.000000 0.048912 0.250000 10.50000 -1.20000 AFIX 0 C24 1 1.500000 0.213713 0.250000 10.50000 0.02642 0.02759 = 0.04447 0.00000 0.00021 0.00000 C20 1 2.000000 -0.189944 0.250000 10.50000 0.03034 0.02226 = 0.04682 0.00000 0.00109 0.00000 HKLF 4 REM m in C222(1) REM R1 = 0.0694 for 2975 Fo > 4sig(Fo) and 0.1019 for all 4349 data REM 255 parameters refined using 32 restraints END ; _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C19 H4.25 Cu N2 Ni O6' _chemical_formula_weight 478.74 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' O O 0.0106 0.0060 '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' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M c2221 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' '-x, y, -z+1/2' 'x, -y, -z' 'x+1/2, y+1/2, z' '-x+1/2, -y+1/2, z+1/2' '-x+1/2, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 12.419(3) _cell_length_b 15.579(3) _cell_length_c 19.680(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3807.5(13) _cell_formula_units_Z 8 _cell_measurement_temperature 103(2) _cell_measurement_reflns_used 17893 _cell_measurement_theta_min 3.10 _cell_measurement_theta_max 27.78 _exptl_crystal_description Block _exptl_crystal_colour green _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.09 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.670 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1898 _exptl_absorpt_coefficient_mu 2.144 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.7405 _exptl_absorpt_correction_T_max 0.7405 _exptl_absorpt_process_details 'SADABS(Sheldrick, 1996)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 103(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'APEX II CCD detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number none _diffrn_standards_interval_count none _diffrn_standards_interval_time none _diffrn_standards_decay_% none _diffrn_reflns_number 17874 _diffrn_reflns_av_R_equivalents 0.1031 _diffrn_reflns_av_unetI/netI 0.0928 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 3.28 _diffrn_reflns_theta_max 27.48 _reflns_number_total 4349 _reflns_number_gt 2975 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Siemens SMART' _computing_cell_refinement 'Siemens SMART & SAINT' _computing_data_reduction 'Siemens XPERP' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. The Ueq for atom O1 and O2 and O6 are higher as compared to neighbors, so the atomic displacement parameters of these atoms were restrained using SIMU and ISOR. A long bond distance between C15 and C17 was displayed. The bond distance between C15 and C17 was restrained using DFIX. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1200P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.02(4) _refine_ls_number_reflns 4349 _refine_ls_number_parameters 255 _refine_ls_number_restraints 32 _refine_ls_R_factor_all 0.1019 _refine_ls_R_factor_gt 0.0694 _refine_ls_wR_factor_ref 0.1987 _refine_ls_wR_factor_gt 0.1728 _refine_ls_goodness_of_fit_ref 0.985 _refine_ls_restrained_S_all 1.002 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu 0.95937(13) 0.02199(9) 0.41996(8) 0.0725(5) Uani 1 1 d . . . Ni1 Ni 1.62782(7) 0.05914(5) 0.26635(4) 0.0309(2) Uani 1 1 d . . . N1 N 0.9389(8) 0.1384(5) 0.3863(4) 0.063(2) Uani 1 1 d . . . N2 N 0.9041(9) -0.0939(5) 0.4296(4) 0.065(2) Uani 1 1 d . . . O1 O 1.1241(11) 0.0200(9) 0.4463(7) 0.139(4) Uani 1 1 d U . . O2 O 1.6192(10) 0.0533(6) 0.3859(5) 0.101(2) Uiso 1 1 d U . . O3 O 1.7919(5) 0.0702(3) 0.2402(4) 0.0573(16) Uani 1 1 d . . . O4 O 1.7121(5) -0.0488(3) 0.2674(4) 0.0571(15) Uani 1 1 d . . . O5 O 1.5901(5) 0.1787(3) 0.2584(3) 0.0464(14) Uani 1 1 d . . . O6 O 1.4880(8) 0.0238(5) 0.3207(5) 0.087(2) Uiso 1 1 d U . . C1 C 0.8426(10) 0.1746(7) 0.3850(6) 0.073(3) Uani 1 1 d . . . H1A H 0.7840 0.1425 0.3997 0.088 Uiso 1 1 calc R . . C2 C 0.8241(17) 0.2583(10) 0.3629(8) 0.108(6) Uani 1 1 d . . . H2A H 0.7557 0.2826 0.3639 0.130 Uiso 1 1 calc R . . C3 C 0.913(2) 0.3036(10) 0.3393(8) 0.109(6) Uani 1 1 d . . . H3A H 0.9047 0.3598 0.3240 0.131 Uiso 1 1 calc R . . C4 C 1.0122(18) 0.2658(10) 0.3385(7) 0.111(6) Uani 1 1 d . . . H4A H 1.0719 0.2945 0.3212 0.133 Uiso 1 1 calc R . . C5 C 1.0215(12) 0.1834(7) 0.3642(6) 0.079(4) Uani 1 1 d . . . H5A H 1.0895 0.1585 0.3659 0.095 Uiso 1 1 calc R . . C6 C 0.8004(12) -0.1093(8) 0.4317(7) 0.083(4) Uani 1 1 d . . . H6A H 0.7533 -0.0630 0.4287 0.100 Uiso 1 1 calc R . . C7 C 0.7577(19) -0.1897(12) 0.4380(10) 0.128(6) Uani 1 1 d U . . H7A H 0.6838 -0.1990 0.4401 0.154 Uiso 1 1 calc R . . C8 C 0.8316(18) -0.2570(11) 0.4410(10) 0.121(6) Uani 1 1 d U . . H8A H 0.8061 -0.3129 0.4454 0.145 Uiso 1 1 calc R . . C9 C 0.9402(18) -0.2435(9) 0.4378(9) 0.115(5) Uani 1 1 d U . . H9A H 0.9895 -0.2884 0.4394 0.138 Uiso 1 1 calc R . . C10 C 0.9725(15) -0.1576(7) 0.4319(6) 0.091(5) Uani 1 1 d . . . H10A H 1.0457 -0.1454 0.4294 0.110 Uiso 1 1 calc R . . C11 C 1.1681(14) 0.0000 0.5000 0.125(11) Uani 1 2 d S . . C12 C 1.2889(13) 0.0000 0.5000 0.064(4) Uani 1 2 d S . . C13 C 1.3447(9) 0.0122(6) 0.4404(5) 0.063(3) Uani 1 1 d . . . H13A H 1.3067 0.0189 0.4000 0.076 Uiso 1 1 calc R . . C15 C 1.5267(11) 0.0316(6) 0.3766(5) 0.073(3) Uani 1 1 d DU . . C17 C 1.4551(8) 0.0146(5) 0.4390(3) 0.047(2) Uani 1 1 d D . . C18 C 1.5115(12) 0.0000 0.5000 0.046(3) Uani 1 2 d S . . H18A H 1.5863 0.0000 0.5000 0.056 Uiso 1 2 calc SR . . C19 C 1.7982(7) -0.0079(4) 0.2534(4) 0.044(2) Uani 1 1 d . . . C21 C 1.9029(6) -0.1444(4) 0.2509(4) 0.0354(16) Uani 1 1 d . . . H21A H 1.8378 -0.1739 0.2516 0.042 Uiso 1 1 calc R . . C22 C 1.9035(6) -0.0546(4) 0.2505(3) 0.0369(16) Uani 1 1 d . . . C23 C 2.0000 -0.0108(6) 0.2500 0.039(3) Uani 1 2 d S . . H23A H 2.0000 0.0489 0.2500 0.047 Uiso 1 2 calc SR . . C24 C 1.5000 0.2137(6) 0.2500 0.033(2) Uani 1 2 d S . . C20 C 2.0000 -0.1899(5) 0.2500 0.033(2) Uani 1 2 d S . . 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 Cu1 0.0652(10) 0.0619(7) 0.0903(10) 0.0105(7) -0.0026(8) 0.0070(6) Ni1 0.0258(4) 0.0256(3) 0.0412(4) 0.0013(3) 0.0032(4) 0.0052(4) N1 0.070(7) 0.052(4) 0.066(5) -0.008(4) -0.019(5) 0.008(4) N2 0.084(8) 0.056(4) 0.054(5) 0.000(3) -0.008(4) 0.017(4) O1 0.091(7) 0.150(7) 0.176(8) 0.058(7) -0.012(7) -0.011(6) O3 0.057(4) 0.030(3) 0.085(4) 0.004(3) 0.019(4) 0.015(3) O4 0.039(3) 0.038(3) 0.095(4) 0.014(3) 0.015(4) 0.006(2) O5 0.038(3) 0.027(2) 0.074(4) -0.005(2) -0.005(3) 0.002(2) C1 0.068(8) 0.071(6) 0.080(7) -0.014(5) -0.025(6) 0.016(5) C2 0.134(16) 0.085(9) 0.105(11) -0.016(8) -0.041(10) 0.053(10) C3 0.18(2) 0.074(9) 0.077(9) 0.007(6) -0.034(11) 0.008(11) C4 0.17(2) 0.093(10) 0.074(9) 0.010(8) 0.006(10) -0.026(11) C5 0.093(11) 0.075(7) 0.069(7) 0.000(5) -0.007(7) -0.021(7) C6 0.078(10) 0.075(7) 0.098(10) -0.001(6) -0.019(8) -0.011(7) C7 0.139(11) 0.115(9) 0.130(9) 0.006(7) -0.018(8) -0.011(8) C8 0.143(10) 0.085(7) 0.134(9) -0.002(7) 0.001(8) -0.010(7) C9 0.142(10) 0.082(7) 0.121(9) -0.014(6) -0.001(8) 0.017(7) C10 0.140(15) 0.069(7) 0.065(7) 0.003(6) -0.010(8) 0.034(8) C11 0.036(9) 0.114(16) 0.22(3) 0.125(19) 0.000 0.000 C12 0.046(8) 0.050(7) 0.097(11) 0.025(7) 0.000 0.000 C13 0.082(9) 0.052(5) 0.056(6) 0.015(4) -0.031(5) -0.009(5) C15 0.124(8) 0.047(4) 0.047(5) -0.010(4) -0.010(5) 0.011(5) C17 0.070(7) 0.047(4) 0.025(4) 0.003(3) -0.004(4) -0.002(4) C18 0.055(8) 0.046(6) 0.038(6) 0.001(5) 0.000 0.000 C19 0.048(5) 0.031(3) 0.053(5) 0.002(3) 0.000(4) 0.013(3) C21 0.024(4) 0.037(3) 0.044(4) -0.004(3) 0.003(3) -0.004(3) C22 0.035(4) 0.031(3) 0.044(4) 0.000(3) 0.005(3) 0.003(3) C23 0.047(7) 0.027(4) 0.045(7) 0.000 0.013(4) 0.000 C24 0.026(5) 0.028(4) 0.044(6) 0.000 0.000(4) 0.000 C20 0.030(6) 0.022(4) 0.047(7) 0.000 0.001(4) 0.000 _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; 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 Cu1 N2 1.942(9) . ? Cu1 N1 1.947(8) . ? Cu1 O1 2.110(14) . ? Ni1 O5 1.927(5) . ? Ni1 O4 1.981(5) . ? Ni1 O3 2.109(7) . ? Ni1 O6 2.112(10) . ? Ni1 O6 2.303(9) 3_855 ? Ni1 O2 2.357(10) . ? Ni1 C19 2.373(8) . ? N1 C5 1.316(16) . ? N1 C1 1.322(14) . ? N2 C10 1.307(15) . ? N2 C6 1.311(17) . ? O1 C11 1.231(14) . ? O2 C15 1.211(15) . ? O3 C19 1.246(9) . ? O4 C19 1.274(10) . ? O5 C24 1.256(7) . ? O6 C15 1.208(13) . ? O6 Ni1 2.303(9) 3_855 ? C1 C2 1.394(18) . ? C2 C3 1.39(3) . ? C3 C4 1.37(3) . ? C4 C5 1.384(19) . ? C6 C7 1.37(2) . ? C7 C8 1.39(3) . ? C8 C9 1.37(2) . ? C9 C10 1.40(2) . ? C11 O1 1.231(14) 4_556 ? C11 C12 1.50(2) . ? C12 C13 1.376(14) 4_556 ? C12 C13 1.376(14) . ? C13 C17 1.371(15) . ? C15 C17 1.539(9) . ? C17 C18 1.409(11) . ? C18 C17 1.409(11) 4_556 ? C19 C22 1.497(10) . ? C21 C20 1.399(8) . ? C21 C22 1.399(10) . ? C22 C23 1.379(9) . ? C23 C22 1.379(9) 3_955 ? C24 O5 1.256(7) 3_855 ? C24 C20 1.501(12) 5_455 ? C20 C21 1.399(8) 3_955 ? C20 C24 1.501(12) 5_545 ? 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 N2 Cu1 N1 148.6(4) . . ? N2 Cu1 O1 107.8(5) . . ? N1 Cu1 O1 102.9(5) . . ? O5 Ni1 O4 161.8(3) . . ? O5 Ni1 O3 97.8(2) . . ? O4 Ni1 O3 63.9(2) . . ? O5 Ni1 O6 95.4(3) . . ? O4 Ni1 O6 102.0(3) . . ? O3 Ni1 O6 159.9(3) . . ? O5 Ni1 O6 91.1(3) . 3_855 ? O4 Ni1 O6 97.7(3) . 3_855 ? O3 Ni1 O6 116.2(3) . 3_855 ? O6 Ni1 O6 78.5(4) . 3_855 ? O5 Ni1 O2 96.2(3) . . ? O4 Ni1 O2 88.9(3) . . ? O3 Ni1 O2 106.9(4) . . ? O6 Ni1 O2 56.5(4) . . ? O6 Ni1 O2 134.8(4) 3_855 . ? O5 Ni1 C19 129.3(3) . . ? O4 Ni1 C19 32.5(2) . . ? O3 Ni1 C19 31.6(2) . . ? O6 Ni1 C19 132.2(3) . . ? O6 Ni1 C19 111.8(3) 3_855 . ? O2 Ni1 C19 97.5(3) . . ? C5 N1 C1 118.1(11) . . ? C5 N1 Cu1 120.4(9) . . ? C1 N1 Cu1 121.5(9) . . ? C10 N2 C6 120.0(12) . . ? C10 N2 Cu1 118.6(11) . . ? C6 N2 Cu1 121.3(8) . . ? C11 O1 Cu1 130.2(12) . . ? C15 O2 Ni1 84.5(7) . . ? C19 O3 Ni1 86.0(5) . . ? C19 O4 Ni1 91.0(4) . . ? C24 O5 Ni1 130.4(5) . . ? C15 O6 Ni1 96.2(8) . . ? C15 O6 Ni1 154.4(8) . 3_855 ? Ni1 O6 Ni1 94.3(3) . 3_855 ? N1 C1 C2 123.7(15) . . ? C3 C2 C1 116.7(15) . . ? C4 C3 C2 120.0(14) . . ? C3 C4 C5 118.1(17) . . ? N1 C5 C4 123.4(16) . . ? N2 C6 C7 123.4(15) . . ? C6 C7 C8 116(2) . . ? C9 C8 C7 122.1(19) . . ? C8 C9 C10 115.7(17) . . ? N2 C10 C9 122.7(18) . . ? O1 C11 O1 127(2) 4_556 . ? O1 C11 C12 116.4(10) 4_556 . ? O1 C11 C12 116.4(10) . . ? C13 C12 C13 119.5(14) 4_556 . ? C13 C12 C11 120.3(7) 4_556 . ? C13 C12 C11 120.3(7) . . ? C17 C13 C12 121.6(9) . . ? O6 C15 O2 122.9(10) . . ? O6 C15 C17 118.7(11) . . ? O2 C15 C17 118.5(10) . . ? C13 C17 C18 118.4(8) . . ? C13 C17 C15 126.8(8) . . ? C18 C17 C15 114.8(10) . . ? C17 C18 C17 120.4(13) . 4_556 ? O3 C19 O4 118.7(8) . . ? O3 C19 C22 121.3(8) . . ? O4 C19 C22 119.9(6) . . ? O3 C19 Ni1 62.4(5) . . ? O4 C19 Ni1 56.6(4) . . ? C22 C19 Ni1 175.2(6) . . ? C20 C21 C22 120.2(7) . . ? C23 C22 C21 119.9(7) . . ? C23 C22 C19 121.3(7) . . ? C21 C22 C19 118.7(7) . . ? C22 C23 C22 120.7(9) . 3_955 ? O5 C24 O5 128.5(9) 3_855 . ? O5 C24 C20 115.8(4) 3_855 5_455 ? O5 C24 C20 115.8(4) . 5_455 ? C21 C20 C21 119.0(8) . 3_955 ? C21 C20 C24 120.5(4) . 5_545 ? C21 C20 C24 120.5(4) 3_955 5_545 ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 1.373 _refine_diff_density_min -0.698 _refine_diff_density_rms 0.116 _database_code_depnum_ccdc_archive 'CCDC 932109'