# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2012 ####################################################################### # # 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_1 _database_code_depnum_ccdc_archive 'CCDC 751631' #TrackingRef 'web_deposit_cif_file_0_AsitR.Sarkar_1352717091.united_structures.cif' ##################################################################### # CHEMICAL INFORMATION # ##################################################################### _chemical_formula_moiety 'C23 H31 Cu N5 O4' _chemical_formula_sum 'C23 H31 Cu N5 O4' _chemical_formula_weight 505.08 ##################################################################### # UNIT CELL INFORMATION # ##################################################################### _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 1 2/c 1 ' _symmetry_space_group_name_Hall '-C 2yc' loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z x+1/2,y+1/2,z -x+1/2,-y+1/2,-z -x,y,-z+1/2 x,-y,z+1/2 -x+1/2,y+1/2,-z+1/2 x+1/2,-y+1/2,z+1/2 _cell_length_a 22.701(6) _cell_length_b 7.0563(19) _cell_length_c 16.741(5) _cell_angle_alpha 90 _cell_angle_beta 121.675(12) _cell_angle_gamma 90 _cell_volume 2282.2(12) _cell_formula_units_Z 4 _cell_measurement_temperature 293 _cell_measurement_reflns_used 435 _cell_measurement_theta_min 4.84 _cell_measurement_theta_max 22.78 ##################################################################### # CRYSTAL INFORMATION # ##################################################################### _exptl_crystal_description rectangular _exptl_crystal_colour 'dark green' _exptl_crystal_size_min 0.09 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_max 0.13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.464 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1060 _exptl_special_details ? ##################################################################### # ABSORPTION CORRECTION # ##################################################################### _exptl_absorpt_coefficient_mu 0.997 _exptl_absorpt_correction_type empirical _exptl_absorpt_process_details 'SADABS (Bruker, 2008)' _exptl_absorpt_correction_T_min 0.729 _exptl_absorpt_correction_T_max 0.905 ##################################################################### # DATA COLLECTION # ##################################################################### _diffrn_ambient_temperature 293 _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART APEX CCD' _diffrn_measurement_method '\j-\w scans' _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8729 _diffrn_reflns_av_R_equivalents 0.057 _diffrn_reflns_limit_h_min -24 _diffrn_reflns_limit_h_max 24 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _reflns_limit_h_min -23 _reflns_limit_h_max 23 _reflns_limit_k_min 0 _reflns_limit_k_max 7 _reflns_limit_l_min 0 _reflns_limit_l_max 18 _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 27.040 _diffrn_measured_fraction_theta_full 0.999 _diffrn_reflns_theta_min 2.508 _diffrn_reflns_theta_max 23.510 _reflns_number_total 3169 _reflns_number_gt 2075 _reflns_threshold_expression I>0.0\s(I) ##################################################################### # COMPUTING PROGRAMS # ##################################################################### _computing_data_collection 'SMART 5.628 (Bruker, 2003)' _computing_cell_refinement 'SAINT 6.45 ( Bruker, 2003)' _computing_data_reduction 'SAINT 6.45 ( Bruker, 2003)' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)' _audit_creation_method 'CRYSTALS (Betteridge et al., 2003)' _computing_publication_material 'CRYSTALS (Betteridge et al., 2003)' _computing_molecular_graphics 'DIAMOND 3.0(Brandenburg,199)' ##################################################################### # REFINEMENT INFORMATION # ##################################################################### _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 > 2sigma(F) 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 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.In the absence of significant anomalous scattering, Friedel pairs were merged. For regularizing the geometry the distance between C17 and C8 restrained to 1.5 angstrom with E.S.D. = 0.05. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method= Modified Sheldrick w=1/[\s^2^(F^2^) + ( 0.10P)^2^ + 0.00P] ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 ; _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method None _refine_ls_extinction_coef ? _refine_ls_number_reflns 1670 _refine_ls_number_parameters 155 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0736 _refine_ls_R_factor_gt 0.0491 _refine_ls_wR_factor_ref 0.1534 _refine_ls_wR_factor_gt 0.1367 _refine_ls_goodness_of_fit_ref 1.0615 _refine_ls_abs_structure_Flack ? _refine_ls_abs_structure_details ? _refine_ls_shift/su_max 0.0001498 _refine_ls_shift/su_mean 0.0000175 _refine_diff_density_max 0.58 _refine_diff_density_min -0.69 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 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C 4.2.6.8 and 6.1.1.4' 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_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_attached_hydrogens Cu1 Cu 0.5000 0.26412(10) 0.2500 0.0535 Uani 1.0000 S T . . . . O2 O 0.56398(16) 0.2009(5) 0.3804(2) 0.0585 Uani 1.0000 . . . . . . C3 C 0.6258(2) 0.1250(5) 0.4170(3) 0.0422 Uani 1.0000 . . . . . . C4 C 0.6634(2) 0.1196(6) 0.3717(3) 0.0436 Uani 1.0000 . . . . . . C5 C 0.6386(2) 0.2108(7) 0.2826(3) 0.0540 Uani 1.0000 . . . . . . N6 N 0.5776(2) 0.2753(5) 0.2292(3) 0.0608 Uani 1.0000 . . . . . . C7 C 0.5642(3) 0.3854(12) 0.1478(5) 0.1037 Uani 1.0000 . . . . . . C8 C 0.5643(9) 0.589(3) 0.1644(12) 0.1798 Uani 1.0000 D . . . . . C9 C 0.7300(2) 0.0339(6) 0.4202(3) 0.0478 Uani 1.0000 . . . . . . C10 C 0.7542(2) -0.0321(7) 0.5081(4) 0.0571 Uani 1.0000 . . . . . . N11 N 0.7194(2) -0.0301(5) 0.5529(3) 0.0563 Uani 1.0000 . . . . . . C12 C 0.6562(2) 0.0453(6) 0.5078(3) 0.0514 Uani 1.0000 . . . . . . C13 C 0.6169(3) 0.0431(10) 0.5571(4) 0.0910 Uani 1.0000 . . . . . . C14 C 0.7732(2) 0.0029(7) 0.3770(4) 0.0617 Uani 1.0000 . . . . . . O15 O 0.74992(17) -0.1552(5) 0.3150(2) 0.0672 Uani 1.0000 . . . . . . N16 N 0.5000 0.5977(9) 0.2500 0.1131 Uani 1.0000 S T . . . . C17 C 0.5693(5) 0.6546(14) 0.2590(17) 0.1705 Uani 1.0000 D . . . . . C18 C 0.5247(13) 0.661(2) 0.3398(14) 0.1669 Uani 0.5000 . . . . . . H51 H 0.6683 0.2212 0.2607 0.0668 Uiso 1.0000 . . . . . . H71 H 0.6008 0.3516 0.1353 0.1268 Uiso 1.0000 . . . . . . H72 H 0.5210 0.3503 0.0945 0.1267 Uiso 1.0000 . . . . . . H81 H 0.6084 0.6389 0.1672 0.2212 Uiso 1.0000 . . . . . . H82 H 0.5282 0.6478 0.1105 0.2212 Uiso 1.0000 . . . . . . H101 H 0.7987 -0.0844 0.5399 0.0697 Uiso 1.0000 . . . . . . H131 H 0.6457 -0.0009 0.6204 0.1329 Uiso 1.0000 . . . . . . H132 H 0.6013 0.1690 0.5567 0.1329 Uiso 1.0000 . . . . . . H133 H 0.5788 -0.0390 0.5254 0.1328 Uiso 1.0000 . . . . . . H141 H 0.8222 -0.0159 0.4277 0.0748 Uiso 1.0000 . . . . . . H142 H 0.7713 0.1137 0.3397 0.0752 Uiso 1.0000 . . . . . . H151 H 0.7633 -0.2367 0.3574 0.1017 Uiso 1.0000 . . . . . . H171 H 0.6108 0.6074 0.3278 0.4910 Uiso 1.00000 . . . . . . H172 H 0.5769 0.8000 0.2822 0.4910 Uiso 1.0000 . . . . . . H181 H 0.4811 0.6400 0.3537 0.1961 Uiso 0.5000 . . . . . . H182 H 0.5288 0.7952 0.3517 0.1961 Uiso 0.5000 . . . . . . H183 H 0.5583 0.5954 0.3912 0.1961 Uiso 0.5000 . . . . . . 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 0.0362(5) 0.0495(5) 0.0655(6) 0.0000 0.0202(4) 0.0000 O2 0.0423(19) 0.072(2) 0.061(2) 0.0022(16) 0.0274(17) 0.0141(16) C3 0.039(2) 0.036(2) 0.049(3) -0.0050(19) 0.022(2) 0.0011(19) C4 0.031(2) 0.042(2) 0.051(3) -0.003(2) 0.018(2) -0.0012(18) C5 0.038(3) 0.066(3) 0.058(3) 0.010(2) 0.025(2) -0.005(2) N6 0.038(2) 0.073(3) 0.061(2) 0.026(2) 0.019(2) -0.0035(19) C7 0.050(3) 0.136(6) 0.099(5) 0.066(5) 0.022(3) -0.016(4) C8 0.135(17) 0.097(2) 0.194(15) 0.110(17) 0.008(13) -0.017(14) C9 0.037(3) 0.046(2) 0.056(3) -0.005(2) 0.022(2) -0.001(2) C10 0.039(3) 0.058(3) 0.058(3) -0.002(2) 0.015(2) 0.010(2) N11 0.055(3) 0.060(2) 0.048(2) 0.0003(19) 0.023(2) 0.004(2) C12 0.050(3) 0.049(3) 0.054(3) -0.007(2) 0.026(2) 0.002(2) C13 0.073(4) 0.142(6) 0.068(4) 0.003(4) 0.044(3) 0.010(4) C14 0.048(3) 0.069(3) 0.072(3) 0.001(3) 0.034(3) 0.004(2) O15 0.072(2) 0.075(2) 0.061(2) 0.0043(19) 0.0391(19) 0.018(2) N16 0.050(4) 0.038(3) 0.151(8) 0.0000 -0.016(4) 0.0000 C17 0.26(7) 0.083(8) 0.091(6) -0.065(19) 0.040(17) 0.007(6) C18 0.21(2) 0.043(8) 0.170(17) -0.061(10) 0.043(16) 0.006(11) ##################################################################### # MOLECULAR GEOMETRY # ##################################################################### 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 N6 1.968(4) 5_655 yes Cu1 O2 1.935(3) 5_655 yes Cu1 O2 1.935(3) . yes Cu1 N6 1.968(4) . yes Cu1 N16 2.354(6) . yes O2 C3 1.314(5) . yes C3 C4 1.410(6) . yes C3 C12 1.414(6) . yes C4 C5 1.440(6) . yes C4 C9 1.422(6) . yes C5 N6 1.275(6) . yes C5 H51 0.923 . no N6 C7 1.456(7) . yes C7 C8 1.47(2) . yes C7 H71 0.986 . no C7 H72 0.948 . no C8 C17 1.596(19) . yes C8 H81 1.038 . no C8 H82 0.938 . no C9 C10 1.355(7) . yes C9 C14 1.510(7) . yes C10 N11 1.345(6) . yes C10 H101 0.936 . no N11 C12 1.331(6) . yes C12 C13 1.500(7) . yes C13 H131 0.960 . no C13 H132 0.956 . no C13 H133 0.940 . no C14 O15 1.423(6) . yes C14 H141 0.993 . no C14 H142 0.987 . no O15 H151 0.838 . no N16 C17 1.552(16) 5_655 yes N16 C18 1.374(18) 5_655 yes N16 C17 1.552(16) . yes N16 C18 1.374(18) . yes C17 H171 1.089 . no C17 H172 1.078 . no C18 H181 1.137 . no C18 H182 0.964 . no C18 H183 0.919 . no 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 N6 Cu1 O2 89.86(15) 5_655 5_655 yes N6 Cu1 O2 91.20(15) 5_655 . yes O2 Cu1 O2 153.4(2) 5_655 . yes N6 Cu1 N6 175.4(2) 5_655 . yes O2 Cu1 N6 91.20(16) 5_655 . yes O2 Cu1 N6 89.86(15) . . yes N6 Cu1 N16 87.69(12) 5_655 . yes O2 Cu1 N16 103.32(11) 5_655 . yes O2 Cu1 N16 103.32(11) . . yes N6 Cu1 N16 87.69(12) . . yes Cu1 O2 C3 127.2(3) . . yes O2 C3 C4 124.0(4) . . yes O2 C3 C12 117.6(4) . . yes C4 C3 C12 118.4(4) . . yes C3 C4 C5 121.9(4) . . yes C3 C4 C9 117.8(4) . . yes C5 C4 C9 120.1(4) . . yes C4 C5 N6 125.1(4) . . yes C4 C5 H51 118.5 . . no N6 C5 H51 116.4 . . no C5 N6 Cu1 127.3(3) . . yes C5 N6 C7 117.5(4) . . yes Cu1 N6 C7 114.9(3) . . yes N6 C7 C8 111.5(9) . . yes N6 C7 H71 106.5 . . no C8 C7 H71 111.1 . . no N6 C7 H72 110.2 . . no C8 C7 H72 109.4 . . no H71 C7 H72 108.0 . . no C7 C8 C17 117.7(8) . . yes C7 C8 H81 104.2 . . no C17 C8 H81 107.1 . . no C7 C8 H82 109.6 . . no C17 C8 H82 113.5 . . no H81 C8 H82 103.3 . . no C4 C9 C10 118.0(4) . . yes C4 C9 C14 123.5(4) . . yes C10 C9 C14 118.4(4) . . yes C9 C10 N11 125.4(4) . . yes C9 C10 H101 117.1 . . no N11 C10 H101 117.5 . . no C10 N11 C12 117.5(4) . . yes C3 C12 N11 122.8(4) . . yes C3 C12 C13 119.9(4) . . yes N11 C12 C13 117.3(4) . . yes C12 C13 H131 110.8 . . no C12 C13 H132 108.2 . . no H131 C13 H132 110.0 . . no C12 C13 H133 109.5 . . no H131 C13 H133 108.3 . . no H132 C13 H133 109.9 . . no C9 C14 O15 112.2(4) . . yes C9 C14 H141 109.1 . . no O15 C14 H141 109.9 . . no C9 C14 H142 111.4 . . no O15 C14 H142 106.5 . . no H141 C14 H142 107.6 . . no C14 O15 H151 95.1 . . no C17 N16 Cu1 105.0(5) 5_655 . yes C17 N16 C18 90.0(13) 5_655 5_655 yes Cu1 N16 C18 108.9(8) . 5_655 yes C17 N16 C17 150.0(10) 5_655 . yes Cu1 N16 C17 105.0(5) . . yes C18 N16 C17 80.4(12) 5_655 . yes C17 N16 C18 80.4(12) 5_655 . yes Cu1 N16 C18 108.9(8) . . yes C18 N16 C18 142.3(16) 5_655 . yes C17 N16 C18 90.0(13) . . yes N16 C17 C8 106.8(11) . . yes N16 C17 H171 107.2 . . no C8 C17 H171 122.1 . . no N16 C17 H172 104.2 . . no C8 C17 H172 123.1 . . no H171 C17 H172 91.4 . . no N16 C18 H181 106.5 . . no N16 C18 H182 119.0 . . no H181 C18 H182 94.8 . . no N16 C18 H183 121.6 . . no H181 C18 H183 97.4 . . no H182 C18 H183 110.9 . . no loop_ _geom_hbond_atom_site_label_D _geom_hbond_site_symmetry_D _geom_hbond_atom_site_label_H _geom_hbond_site_symmetry_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_angle_DHA _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_publ_flag O15 . H151 . N11 4_646 169.6(3) 0.838 2.120 2.948(13) yes C18 . H181 . C7 5_655 126.2(7) 1.137 2.064 2.885(13) yes C8 5_655 H181 . C18 . 150.8(11) 0.978 1.137 2.046(13) yes data_2 _database_code_depnum_ccdc_archive 'CCDC 902897' #TrackingRef 'web_deposit_cif_file_0_AsitR.Sarkar_1352717091.united_structures.cif' ##################################################################### # CHEMICAL INFORMATION # ##################################################################### _chemical_name_systematic ? _chemical_name_common ? _chemical_formula_moiety 'C23 H31 N5 Ni O4, 2(H2 O)' _chemical_formula_sum 'C23 H35 N5 Ni O6' _chemical_formula_weight 536.25 _chemical_melting_point ? _chemical_compound_source ? ##################################################################### # UNIT CELL INFORMATION # ##################################################################### _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 2/c' _symmetry_space_group_name_Hall '-C 2yc' loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z x+1/2,y+1/2,z -x+1/2,-y+1/2,-z -x,y,-z+1/2 x,-y,z+1/2 -x+1/2,y+1/2,-z+1/2 x+1/2,-y+1/2,z+1/2 _cell_length_a 22.768(4) _cell_length_b 7.0751(10) _cell_length_c 18.218(3) _cell_angle_alpha 90 _cell_angle_beta 118.618(8) _cell_angle_gamma 90 _cell_volume 2576.1(7) _cell_formula_units_Z 4 _cell_measurement_temperature 293 _cell_measurement_reflns_used 432 _cell_measurement_theta_min 5.04 _cell_measurement_theta_max 23.66 ##################################################################### # CRYSTAL INFORMATION # ##################################################################### _exptl_crystal_description rectangular _exptl_crystal_colour green _exptl_crystal_size_min 0.07 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_max 0.17 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.383 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1136 _exptl_special_details ? ##################################################################### # ABSORPTION CORRECTION # ##################################################################### _exptl_absorpt_coefficient_mu 0.800 _exptl_absorpt_correction_type empirical _exptl_absorpt_process_details 'SADABS (Bruker, 2008)' _exptl_absorpt_correction_T_min 0.9091 _exptl_absorpt_correction_T_max 0.9450 ##################################################################### # DATA COLLECTION # ##################################################################### _diffrn_ambient_temperature 293 _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 'Bruker SMART APEX CCD' _diffrn_measurement_method '\j-\w scans' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 14273 _diffrn_reflns_av_R_equivalents 0.066 _diffrn_reflns_limit_h_min -27 _diffrn_reflns_limit_h_max 27 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 25.265 _diffrn_measured_fraction_theta_full 0.996 _diffrn_reflns_theta_min 2.038 _diffrn_reflns_theta_max 25.265 _reflns_number_total 2322 _reflns_number_gt 1950 _reflns_threshold_expression I>2.0\s(I) ##################################################################### # COMPUTING PROGRAMS # ##################################################################### _computing_data_collection 'SMART 5.628 (Bruker, 2003)' _computing_cell_refinement 'SMART 5.628 (Bruker, 2003)' _computing_data_reduction 'SAINT 6.45 ( Bruker, 2003)' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)' _audit_creation_method 'CRYSTALS (Betteridge et al., 2003)' _computing_publication_material 'CRYSTALS (Betteridge et al., 2003)' _computing_molecular_graphics 'DIAMOND 3.0(Brandenburg,199)' ##################################################################### # REFINEMENT INFORMATION # ##################################################################### _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 > 2sigma(F) 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 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.In the absence of significant anomalous scattering, Friedel pairs were merged. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method= Modified Sheldrick w=1/[\s^2^(F^2^) + ( 0.08P)^2^ +10.49P], where P=(max(Fo^2^,0) + 2Fc^2^)/3 ; _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2320 _refine_ls_number_parameters 173 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0605 _refine_ls_R_factor_gt 0.0494 _refine_ls_wR_factor_ref 0.1531 _refine_ls_wR_factor_gt 0.1439 _refine_ls_goodness_of_fit_ref 1.0490 _refine_ls_restrained_S_all 1.0490 _refine_ls_abs_structure_Flack ? _refine_ls_abs_structure_details ? _refine_ls_shift/su_max 0.0001899 _refine_ls_shift/su_mean 0.0000176 _refine_diff_density_max 0.66 _refine_diff_density_min -0.61 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 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C 4.2.6.8 and 6.1.1.4' Ni Ni 0.3393 1.1124 'International Tables Vol C 4.2.6.8 and 6.1.1.4' 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_occupancy _atom_site_adp_type _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group Ni1 Ni 0.5000 0.69035(10) 0.2500 0.0272 1.0000 Uani S T . . . O2 O 0.55714(14) 0.7804(4) 0.36458(17) 0.0334 1.0000 Uani . . . . . C3 C 0.6183(2) 0.8510(5) 0.3970(2) 0.0270 1.0000 Uani . . . . . C4 C 0.65893(19) 0.8435(5) 0.3590(2) 0.0265 1.0000 Uani . . . . . C5 C 0.63817(19) 0.7564(5) 0.2780(2) 0.0264 1.0000 Uani . . . . . N6 N 0.57930(17) 0.6919(5) 0.2299(2) 0.0302 1.0000 Uani . . . . . C7 C 0.5680(2) 0.5915(6) 0.1542(2) 0.0345 1.0000 Uani . . . . . C8 C 0.5619(2) 0.3786(7) 0.1650(3) 0.0460 1.0000 Uani . . . . . C9 C 0.5574(4) 0.3161(14) 0.2429(6) 0.0410 0.5000 Uani . . . 1 1 C10 C 0.4984(5) 0.3278(13) 0.1731(6) 0.0412 0.5000 Uani D . . 1 1 N11 N 0.5000 0.3942(7) 0.2500 0.0340 1.0000 Uani S T . . . C12 C 0.4362(4) 0.3258(13) 0.1732(6) 0.0420 0.5000 Uani . . . . . C13 C 0.72459(19) 0.9185(5) 0.4034(2) 0.0256 1.0000 Uani . . . . . C14 C 0.7444(2) 0.9996(5) 0.4805(2) 0.0291 1.0000 Uani . . . . . N15 N 0.70445(17) 1.0122(5) 0.51576(19) 0.0302 1.0000 Uani . . . . . C16 C 0.6437(2) 0.9422(6) 0.4763(2) 0.0293 1.0000 Uani . . . . . C17 C 0.5999(2) 0.9586(7) 0.5165(3) 0.0375 1.0000 Uani . . . . . C18 C 0.7730(2) 0.9138(6) 0.3692(2) 0.0313 1.0000 Uani . . . . . O19 O 0.75064(15) 1.0227(4) 0.29466(17) 0.0352 1.0000 Uani . . . . . O20 O 0.77714(14) 1.1337(4) 0.67841(16) 0.0324 1.0000 Uani . . . . . H51 H 0.6698 0.7482 0.2595 0.0318 1.0000 Uiso R . . . . H72 H 0.6040 0.6151 0.1423 0.0407 1.0000 Uiso R . . . . H71 H 0.5267 0.6366 0.1092 0.0404 1.0000 Uiso R . . . . H141 H 0.7877 1.0489 0.5101 0.0343 1.0000 Uiso R . . . . H171 H 0.6239 1.0278 0.5670 0.0559 1.0000 Uiso R . . . . H172 H 0.5591 1.0237 0.4818 0.0560 1.0000 Uiso R . . . . H173 H 0.5902 0.8358 0.5294 0.0559 1.0000 Uiso R . . . . H182 H 0.8150 0.9703 0.4117 0.0376 1.0000 Uiso R . . . . H181 H 0.7810 0.7835 0.3583 0.0378 1.0000 Uiso R . . . . H201 H 0.7743 1.0802 0.7164 0.0484 1.0000 Uiso R . . . . H202 H 0.7539 1.0989 0.6302 0.0485 1.0000 Uiso R . . . . H191 H 0.7330 1.1220 0.2971 0.0530 1.0000 Uiso R . . . . H121 H 0.3979 0.3754 0.1746 0.0505 0.5000 Uiso DR . . . . H122 H 0.4367 0.3735 0.1241 0.0505 0.5000 Uiso R . . . . H123 H 0.4353 0.1940 0.1721 0.0505 0.5000 Uiso R . . . . H101 H 0.4943 0.1924 0.1722 0.0492 0.5000 Uiso R . . 1 1 H102 H 0.4605 0.3797 0.1278 0.0492 0.5000 Uiso DR . . 1 1 H91 H 0.5975 0.3541 0.2914 0.0494 0.5000 Uiso R . . 1 1 H92 H 0.5543 0.1818 0.2426 0.0494 0.5000 Uiso R . . 1 1 H81 H 0.6006 0.3368 0.2134 0.0550 1.0000 Uiso R . . . . H82 H 0.5595 0.3137 0.1172 0.0550 1.0000 Uiso R . . . . 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 0.0294(4) 0.0296(4) 0.0223(4) 0.0000 0.0122(3) 0.0000 O2 0.0336(16) 0.0404(17) 0.0286(14) -0.0070(12) 0.0169(12) -0.0067(13) C3 0.035(2) 0.0219(19) 0.0195(17) 0.0020(14) 0.0095(16) 0.0011(16) C4 0.031(2) 0.0216(19) 0.0250(18) 0.0052(15) 0.0124(16) 0.0037(15) C5 0.032(2) 0.0243(19) 0.0248(18) 0.0013(15) 0.0147(17) 0.0013(16) N6 0.0342(19) 0.0304(18) 0.0274(16) -0.0020(14) 0.0157(15) 0.0019(15) C7 0.032(2) 0.046(3) 0.028(2) -0.0122(18) 0.0162(17) -0.0021(19) C8 0.052(3) 0.040(3) 0.054(3) -0.021(2) 0.031(2) -0.003(2) C9 0.032(5) 0.037(5) 0.051(5) -0.005(4) 0.018(4) -0.004(4) C10 0.044(5) 0.032(5) 0.046(5) -0.008(4) 0.021(4) -0.002(4) N11 0.029(3) 0.031(3) 0.037(3) 0.0000 0.013(2) 0.0000 C12 0.035(5) 0.031(5) 0.049(5) -0.002(4) 0.012(4) 0.000(4) C13 0.032(2) 0.0213(19) 0.0230(17) 0.0037(14) 0.0131(16) 0.0022(16) C14 0.035(2) 0.0263(19) 0.0227(18) 0.0029(15) 0.0110(17) -0.0034(17) N15 0.042(2) 0.0267(17) 0.0212(15) 0.0006(13) 0.0149(15) -0.0020(15) C16 0.038(2) 0.027(2) 0.0238(18) 0.0038(16) 0.0155(17) 0.0028(17) C17 0.043(3) 0.047(3) 0.028(2) -0.0031(19) 0.0213(19) 0.001(2) C18 0.036(2) 0.032(2) 0.0267(19) 0.0021(17) 0.0162(17) -0.0022(18) O19 0.0550(19) 0.0297(15) 0.0304(14) 0.0017(12) 0.0282(14) 0.0013(13) O20 0.0434(17) 0.0308(15) 0.0225(13) -0.0009(11) 0.0154(12) -0.0032(12) ##################################################################### # MOLECULAR GEOMETRY # ##################################################################### 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 Ni1 N6 2.006(3) 5_655 yes Ni1 O2 1.963(3) 5_655 yes Ni1 O2 1.963(3) . yes Ni1 N6 2.006(3) . yes Ni1 N11 2.095(5) . yes O2 C3 1.322(5) . yes C3 C4 1.397(6) . yes C3 C16 1.427(5) . yes C4 C5 1.454(5) . yes C4 C13 1.418(6) . yes C5 N6 1.283(5) . yes C5 H51 0.931 . no N6 C7 1.462(5) . yes C7 C8 1.534(7) . yes C7 H72 0.957 . no C7 H71 0.959 . no C8 C9 1.535(11) . yes C8 C10 1.563(10) . yes C8 H81 0.944 . no C8 H82 0.958 . no C9 N11 1.481(9) . yes C9 H92 0.950 . no C9 H91 0.965 . no C10 N11 1.462(9) . yes C10 H101 0.960 . no C10 H102 0.940 . no N11 C12 1.535(9) 5_655 yes N11 C12 1.535(9) . yes C12 H123 0.930 . no C12 H121 0.949 . no C12 H122 0.951 . no C13 C14 1.378(5) . yes C13 C18 1.505(5) . yes C14 N15 1.345(5) . yes C14 H141 0.936 . no N15 C16 1.313(5) . yes C16 C17 1.497(5) . yes C17 H171 0.951 . no C17 H172 0.954 . no C17 H173 0.954 . no C18 O19 1.426(5) . yes C18 H182 0.982 . no C18 H181 0.978 . no O19 H191 0.821 . no O20 H201 0.817 . no O20 H202 0.816 . no loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_3 _geom_angle_publ_flag N6 Ni1 O2 89.77(12) 5_655 5_655 yes N6 Ni1 O2 90.02(12) 5_655 . yes O2 Ni1 O2 142.12(18) 5_655 . yes N6 Ni1 N6 179.4(2) 5_655 . yes O2 Ni1 N6 90.02(12) 5_655 . yes O2 Ni1 N6 89.77(12) . . yes N6 Ni1 N11 90.32(10) 5_655 . yes O2 Ni1 N11 108.94(9) 5_655 . yes O2 Ni1 N11 108.94(9) . . yes N6 Ni1 N11 90.32(10) . . yes Ni1 O2 C3 128.1(2) . . yes O2 C3 C4 124.8(3) . . yes O2 C3 C16 116.9(3) . . yes C4 C3 C16 118.4(4) . . yes C3 C4 C5 123.3(4) . . yes C3 C4 C13 118.1(3) . . yes C5 C4 C13 118.6(3) . . yes C4 C5 N6 124.7(4) . . yes C4 C5 H51 117.5 . . no N6 C5 H51 117.8 . . no C5 N6 Ni1 127.9(3) . . yes C5 N6 C7 118.1(3) . . yes Ni1 N6 C7 113.8(3) . . yes N6 C7 C8 110.0(3) . . yes N6 C7 H72 110.3 . . no C8 C7 H72 110.0 . . no N6 C7 H71 107.6 . . no C8 C7 H71 108.9 . . no H72 C7 H71 110.1 . . no C7 C8 C9 116.9(5) . . yes C7 C8 C10 112.5(5) . . yes C9 C8 C10 51.2(5) . . yes C7 C8 H81 116.6 . . no C9 C8 H81 126.1 . . no C10 C8 H81 101.7 . . no C7 C8 H82 116.9 . . no C9 C8 H82 98.8 . . no C10 C8 H82 130.1 . . no H81 C8 H82 61.3 . . no C8 C9 N11 115.2(7) . . yes C8 C9 H92 119.2 . . no N11 C9 H92 106.6 . . no C8 C9 H91 109.0 . . no N11 C9 H91 109.3 . . no H92 C9 H91 95.5 . . no C8 C10 N11 114.7(6) . . yes C8 C10 H101 106.3 . . no N11 C10 H101 106.3 . . no C8 C10 H102 111.3 . . no N11 C10 H102 109.7 . . no H101 C10 H102 108.1 . . no C12 N11 C9 58.2(5) 5_655 . yes C12 N11 C9 107.0(5) 5_655 5_655 yes C9 N11 C9 136.1(8) . 5_655 yes C12 N11 C10 110.5(6) 5_655 . yes C9 N11 C10 54.1(5) . . yes C9 N11 C10 110.3(5) 5_655 . yes C12 N11 C10 56.4(5) 5_655 5_655 yes C9 N11 C10 110.3(5) . 5_655 yes C9 N11 C10 54.1(5) 5_655 5_655 yes C10 N11 C10 142.5(8) . 5_655 yes C12 N11 Ni1 108.4(4) 5_655 . yes C9 N11 Ni1 111.9(4) . . yes C9 N11 Ni1 111.9(4) 5_655 . yes C10 N11 Ni1 108.8(4) . . yes C10 N11 Ni1 108.8(4) 5_655 . yes C12 N11 C12 143.2(8) 5_655 . yes C9 N11 C12 107.0(5) . . yes C9 N11 C12 58.2(5) 5_655 . yes C10 N11 C12 56.4(5) . . yes C10 N11 C12 110.5(6) 5_655 . yes Ni1 N11 C12 108.4(4) . . yes N11 C12 H123 97.2 . . no N11 C12 H121 109.0 . . no H123 C12 H121 115.2 . . no N11 C12 H122 110.8 . . no H123 C12 H122 112.5 . . no H121 C12 H122 111.3 . . no C4 C13 C14 118.5(3) . . yes C4 C13 C18 122.5(3) . . yes C14 C13 C18 119.0(4) . . yes C13 C14 N15 123.3(4) . . yes C13 C14 H141 118.9 . . no N15 C14 H141 117.9 . . no C14 N15 C16 119.3(3) . . yes C3 C16 N15 122.3(4) . . yes C3 C16 C17 119.2(4) . . yes N15 C16 C17 118.5(3) . . yes C16 C17 H171 107.8 . . no C16 C17 H172 112.3 . . no H171 C17 H172 108.5 . . no C16 C17 H173 109.7 . . no H171 C17 H173 108.8 . . no H172 C17 H173 109.6 . . no C13 C18 O19 112.6(3) . . yes C13 C18 H182 107.1 . . no O19 C18 H182 107.4 . . no C13 C18 H181 110.4 . . no O19 C18 H181 109.4 . . no H182 C18 H181 109.8 . . no C18 O19 H191 111.8 . . no H201 O20 H202 119.8 . . no loop_ _geom_hbond_atom_site_label_D _geom_hbond_site_symmetry_D _geom_hbond_atom_site_label_H _geom_hbond_site_symmetry_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_angle_DHA _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_publ_flag O20 . H201 . O19 6_575 168.67(12) 0.817 1.895 2.701(8) yes O20 . H202 . N15 . 176.00(13) 0.816 1.935 2.750(8) yes O19 . H191 . O20 4_676 160.97(13) 0.821 1.827 2.617(8) yes