# Supplementary Material (ESI) for CrystEngComm # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_coden_Cambridge 1350 loop_ _publ_author_name 'Cincic, Dominik' 'Kaitner, Branko' _publ_contact_author_name 'Cincic, Dominik' _publ_contact_author_email dominik@chem.pmf.hr _publ_section_title ; Schiff base derived from 2-hydroxy-1-naphthaldehyde and liquid-assisted mechanochemical synthesis of its isostructural Cu(II) and Co(II) complexes ; # Attachment '- Compound 1_Cincic.cif' data_Compound_1_Cincic&Kaitner _database_code_depnum_ccdc_archive 'CCDC 784718' #TrackingRef '- Compound 1_Cincic.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 1-[(2-biphenylamino)methylen]naphtalen-2(1H)-one _chemical_melting_point ? _chemical_formula_moiety 'C23 H17 N O' _chemical_formula_sum 'C23 H17 N O' _chemical_formula_weight 323.38 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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 6.1078(2) _cell_length_b 9.0766(3) _cell_length_c 30.1945(11) _cell_angle_alpha 90.00 _cell_angle_beta 92.094(3) _cell_angle_gamma 90.00 _cell_volume 1672.81(10) _cell_formula_units_Z 4 _cell_measurement_temperature 293 _cell_measurement_reflns_used 2109 _cell_measurement_theta_min 5 _cell_measurement_theta_max 25 _exptl_crystal_description prisms _exptl_crystal_colour yellow _exptl_crystal_size_max 0.49 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.284 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 680 _exptl_absorpt_coefficient_mu 0.078 _exptl_absorpt_correction_type analytical _exptl_absorpt_correction_T_min 0.97712 _exptl_absorpt_correction_T_max 0.99442 _exptl_absorpt_process_details 'N.W. Alcock (1970). Cryst. Computing, p271' _exptl_special_details ; ? ; _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 ; Oxford Diffraction Xcalibur CCD diffractometer ; _diffrn_measurement_method 'omega scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11315 _diffrn_reflns_av_R_equivalents 0.0426 _diffrn_reflns_av_sigmaI/netI 0.0624 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -38 _diffrn_reflns_limit_l_max 38 _diffrn_reflns_theta_min 4.05 _diffrn_reflns_theta_max 25.99 _reflns_number_total 3251 _reflns_number_gt 1781 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlis CCD 170 (Oxford Diffraction, 2003) ; _computing_cell_refinement ; CrysAlis RED 170 (Oxford Diffraction, 2003) ; _computing_data_reduction ; CrysAlis RED 170 (Oxford Diffraction, 2003) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-3 (Farrugia, 1997)' _computing_publication_material ? _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. ; _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^)+(0.0563P)^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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3251 _refine_ls_number_parameters 227 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1223 _refine_ls_R_factor_gt 0.0528 _refine_ls_wR_factor_ref 0.1174 _refine_ls_wR_factor_gt 0.0995 _refine_ls_goodness_of_fit_ref 0.949 _refine_ls_restrained_S_all 0.949 _refine_ls_shift/su_max 0.000 _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 O1 O 0.2236(2) 0.39147(17) 0.40358(5) 0.0618(4) Uani 1 1 d . . . N1 N 0.4417(2) 0.17550(18) 0.37411(5) 0.0417(4) Uani 1 1 d . . . C1 C 0.1174(3) 0.2684(2) 0.33679(6) 0.0387(5) Uani 1 1 d . . . C2 C 0.0844(3) 0.3743(2) 0.37074(7) 0.0448(5) Uani 1 1 d . . . C3 C -0.1114(3) 0.4603(2) 0.36895(7) 0.0525(6) Uani 1 1 d . . . H3 H -0.1360 0.5280 0.3914 0.063 Uiso 1 1 calc R . . C4 C -0.2604(3) 0.4453(2) 0.33552(7) 0.0503(6) Uani 1 1 d . . . H4 H -0.3875 0.5016 0.3357 0.060 Uiso 1 1 calc R . . C5 C -0.2304(3) 0.3457(2) 0.29968(6) 0.0411(5) Uani 1 1 d . . . C6 C -0.3880(3) 0.3333(2) 0.26480(7) 0.0515(6) Uani 1 1 d . . . H6 H -0.5139 0.3908 0.2651 0.062 Uiso 1 1 calc R . . C7 C -0.3594(3) 0.2383(3) 0.23054(7) 0.0561(6) Uani 1 1 d . . . H7 H -0.4653 0.2306 0.2077 0.067 Uiso 1 1 calc R . . C8 C -0.1712(3) 0.1531(2) 0.23003(7) 0.0531(6) Uani 1 1 d . . . H8 H -0.1513 0.0884 0.2066 0.064 Uiso 1 1 calc R . . C9 C -0.0144(3) 0.1626(2) 0.26338(7) 0.0481(5) Uani 1 1 d . . . H9 H 0.1117 0.1056 0.2620 0.058 Uiso 1 1 calc R . . C10 C -0.0402(3) 0.2575(2) 0.29995(6) 0.0389(5) Uani 1 1 d . . . C11 C 0.2941(3) 0.1694(2) 0.34153(6) 0.0415(5) Uani 1 1 d . . . H11 H 0.3068 0.0956 0.3204 0.050 Uiso 1 1 calc R . . C12 C 0.6217(3) 0.0783(2) 0.37976(7) 0.0399(5) Uani 1 1 d . . . C13 C 0.6867(3) -0.0135(2) 0.34589(7) 0.0521(6) Uani 1 1 d . . . H13 H 0.6075 -0.0139 0.3190 0.063 Uiso 1 1 calc R . . C14 C 0.8663(3) -0.1040(3) 0.35150(8) 0.0616(6) Uani 1 1 d . . . H14 H 0.9062 -0.1663 0.3287 0.074 Uiso 1 1 calc R . . C15 C 0.9871(3) -0.1020(3) 0.39095(9) 0.0610(6) Uani 1 1 d . . . H15 H 1.1093 -0.1623 0.3949 0.073 Uiso 1 1 calc R . . C16 C 0.9252(3) -0.0098(2) 0.42448(7) 0.0522(6) Uani 1 1 d . . . H16 H 1.0082 -0.0085 0.4509 0.063 Uiso 1 1 calc R . . C17 C 0.7424(3) 0.0816(2) 0.42015(7) 0.0424(5) Uani 1 1 d . . . C18 C 0.6832(3) 0.1759(2) 0.45809(6) 0.0419(5) Uani 1 1 d . . . C19 C 0.8355(3) 0.2713(2) 0.47745(7) 0.0534(6) Uani 1 1 d . . . H19 H 0.9730 0.2804 0.4655 0.064 Uiso 1 1 calc R . . C20 C 0.7859(4) 0.3528(3) 0.51417(8) 0.0617(7) Uani 1 1 d . . . H20 H 0.8908 0.4156 0.5269 0.074 Uiso 1 1 calc R . . C21 C 0.5835(4) 0.3427(3) 0.53222(7) 0.0609(6) Uani 1 1 d . . . H21 H 0.5506 0.3985 0.5569 0.073 Uiso 1 1 calc R . . C22 C 0.4304(3) 0.2492(3) 0.51340(8) 0.0589(6) Uani 1 1 d . . . H22 H 0.2930 0.2413 0.5255 0.071 Uiso 1 1 calc R . . C23 C 0.4791(3) 0.1668(2) 0.47658(7) 0.0530(6) Uani 1 1 d . . . H23 H 0.3735 0.1042 0.4640 0.064 Uiso 1 1 calc R . . H1 H 0.4182 0.2585 0.3974 0.146(12) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0632(9) 0.0713(11) 0.0498(9) -0.0189(8) -0.0109(8) 0.0034(8) N1 0.0413(9) 0.0457(10) 0.0378(9) -0.0008(8) -0.0019(8) -0.0020(8) C1 0.0393(10) 0.0406(12) 0.0363(11) 0.0014(10) 0.0018(9) -0.0020(9) C2 0.0483(12) 0.0464(13) 0.0397(12) 0.0007(10) 0.0014(10) -0.0029(11) C3 0.0651(13) 0.0483(14) 0.0444(13) -0.0048(11) 0.0060(11) 0.0068(11) C4 0.0505(12) 0.0461(14) 0.0545(14) 0.0042(11) 0.0039(11) 0.0114(10) C5 0.0444(11) 0.0364(12) 0.0427(12) 0.0065(10) 0.0029(9) -0.0008(10) C6 0.0478(12) 0.0494(14) 0.0567(14) 0.0092(12) -0.0059(11) 0.0061(11) C7 0.0552(13) 0.0594(15) 0.0524(14) 0.0024(12) -0.0172(11) -0.0003(12) C8 0.0572(13) 0.0572(15) 0.0443(13) -0.0069(11) -0.0054(11) -0.0017(12) C9 0.0439(11) 0.0557(14) 0.0444(12) -0.0037(11) -0.0018(10) 0.0041(10) C10 0.0407(11) 0.0395(12) 0.0367(11) 0.0037(10) 0.0023(9) -0.0042(10) C11 0.0427(10) 0.0458(13) 0.0357(11) 0.0000(10) -0.0004(9) -0.0063(10) C12 0.0366(10) 0.0383(12) 0.0447(12) 0.0007(10) -0.0006(9) -0.0038(10) C13 0.0506(12) 0.0529(14) 0.0523(14) -0.0074(12) -0.0048(11) 0.0024(11) C14 0.0612(14) 0.0530(15) 0.0708(17) -0.0094(13) 0.0030(13) 0.0087(12) C15 0.0469(12) 0.0588(15) 0.0771(18) 0.0083(14) 0.0011(13) 0.0079(12) C16 0.0418(11) 0.0634(15) 0.0511(14) 0.0092(12) -0.0032(10) -0.0007(11) C17 0.0348(10) 0.0467(13) 0.0453(13) 0.0084(10) -0.0019(9) -0.0075(10) C18 0.0373(11) 0.0510(13) 0.0371(11) 0.0079(10) -0.0040(9) -0.0023(10) C19 0.0433(12) 0.0706(16) 0.0461(13) 0.0029(12) -0.0024(10) -0.0109(11) C20 0.0576(14) 0.0721(17) 0.0546(15) -0.0040(14) -0.0087(12) -0.0146(13) C21 0.0683(15) 0.0673(16) 0.0470(14) -0.0044(12) -0.0006(12) 0.0010(13) C22 0.0492(13) 0.0763(17) 0.0515(14) 0.0039(14) 0.0087(11) -0.0015(12) C23 0.0415(12) 0.0647(15) 0.0524(14) 0.0012(12) -0.0018(10) -0.0096(11) _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 O1 C2 1.292(2) . ? N1 C11 1.311(2) . ? N1 C12 1.415(2) . ? N1 H1 1.0440 . ? C1 C11 1.407(3) . ? C1 C2 1.425(3) . ? C1 C10 1.447(2) . ? C2 C3 1.428(3) . ? C3 C4 1.341(3) . ? C3 H3 0.9300 . ? C4 C5 1.426(3) . ? C4 H4 0.9300 . ? C5 C6 1.405(3) . ? C5 C10 1.411(2) . ? C6 C7 1.363(3) . ? C6 H6 0.9300 . ? C7 C8 1.386(3) . ? C7 H7 0.9300 . ? C8 C9 1.367(3) . ? C8 H8 0.9300 . ? C9 C10 1.413(3) . ? C9 H9 0.9300 . ? C11 H11 0.9300 . ? C12 C13 1.388(3) . ? C12 C17 1.402(2) . ? C13 C14 1.376(3) . ? C13 H13 0.9300 . ? C14 C15 1.378(3) . ? C14 H14 0.9300 . ? C15 C16 1.377(3) . ? C15 H15 0.9300 . ? C16 C17 1.393(3) . ? C16 H16 0.9300 . ? C17 C18 1.485(3) . ? C18 C19 1.385(3) . ? C18 C23 1.387(3) . ? C19 C20 1.376(3) . ? C19 H19 0.9300 . ? C20 C21 1.372(3) . ? C20 H20 0.9300 . ? C21 C22 1.370(3) . ? C21 H21 0.9300 . ? C22 C23 1.382(3) . ? C22 H22 0.9300 . ? C23 H23 0.9300 . ? 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 C11 N1 C12 125.02(17) . . ? C11 N1 H1 115.34 . . ? C12 N1 H1 119.63 . . ? C11 C1 C2 119.06(17) . . ? C11 C1 C10 121.35(18) . . ? C2 C1 C10 119.42(17) . . ? O1 C2 C1 121.81(18) . . ? O1 C2 C3 119.32(19) . . ? C1 C2 C3 118.84(18) . . ? C4 C3 C2 121.1(2) . . ? C4 C3 H3 119.4 . . ? C2 C3 H3 119.4 . . ? C3 C4 C5 122.24(19) . . ? C3 C4 H4 118.9 . . ? C5 C4 H4 118.9 . . ? C6 C5 C10 120.00(19) . . ? C6 C5 C4 121.08(18) . . ? C10 C5 C4 118.91(17) . . ? C7 C6 C5 121.1(2) . . ? C7 C6 H6 119.4 . . ? C5 C6 H6 119.4 . . ? C6 C7 C8 119.40(19) . . ? C6 C7 H7 120.3 . . ? C8 C7 H7 120.3 . . ? C9 C8 C7 121.0(2) . . ? C9 C8 H8 119.5 . . ? C7 C8 H8 119.5 . . ? C8 C9 C10 121.27(19) . . ? C8 C9 H9 119.4 . . ? C10 C9 H9 119.4 . . ? C5 C10 C9 117.16(17) . . ? C5 C10 C1 119.34(18) . . ? C9 C10 C1 123.51(18) . . ? N1 C11 C1 123.57(18) . . ? N1 C11 H11 118.2 . . ? C1 C11 H11 118.2 . . ? C13 C12 C17 119.88(18) . . ? C13 C12 N1 121.82(17) . . ? C17 C12 N1 118.22(18) . . ? C14 C13 C12 121.0(2) . . ? C14 C13 H13 119.5 . . ? C12 C13 H13 119.5 . . ? C13 C14 C15 119.9(2) . . ? C13 C14 H14 120.1 . . ? C15 C14 H14 120.1 . . ? C16 C15 C14 119.4(2) . . ? C16 C15 H15 120.3 . . ? C14 C15 H15 120.3 . . ? C15 C16 C17 122.2(2) . . ? C15 C16 H16 118.9 . . ? C17 C16 H16 118.9 . . ? C16 C17 C12 117.57(19) . . ? C16 C17 C18 119.19(18) . . ? C12 C17 C18 123.24(17) . . ? C19 C18 C23 117.87(19) . . ? C19 C18 C17 120.46(18) . . ? C23 C18 C17 121.60(18) . . ? C20 C19 C18 120.8(2) . . ? C20 C19 H19 119.6 . . ? C18 C19 H19 119.6 . . ? C21 C20 C19 120.8(2) . . ? C21 C20 H20 119.6 . . ? C19 C20 H20 119.6 . . ? C22 C21 C20 119.2(2) . . ? C22 C21 H21 120.4 . . ? C20 C21 H21 120.4 . . ? C21 C22 C23 120.3(2) . . ? C21 C22 H22 119.8 . . ? C23 C22 H22 119.8 . . ? C22 C23 C18 121.0(2) . . ? C22 C23 H23 119.5 . . ? C18 C23 H23 119.5 . . ? _diffrn_measured_fraction_theta_max 0.983 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.987 _refine_diff_density_max 0.126 _refine_diff_density_min -0.158 _refine_diff_density_rms 0.040 # Attachment '- Compound 2_Cincic.cif' data_Compound_2_Cincic&Kaitner _database_code_depnum_ccdc_archive 'CCDC 784719' #TrackingRef '- Compound 2_Cincic.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common bis[N-(2-biphenyl)-2-oxy-1-naphthaldiminato]copper(II) _chemical_melting_point ? _chemical_formula_moiety 'C46 H32 Cu N2 O2' _chemical_formula_sum 'C46 H32 Cu N2 O2' _chemical_formula_weight 708.28 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' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _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+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 25.3539(10) _cell_length_b 9.1936(2) _cell_length_c 15.1458(6) _cell_angle_alpha 90.00 _cell_angle_beta 106.930(4) _cell_angle_gamma 90.00 _cell_volume 3377.4(2) _cell_formula_units_Z 4 _cell_measurement_temperature 293 _cell_measurement_reflns_used 4888 _cell_measurement_theta_min 5 _cell_measurement_theta_max 28 _exptl_crystal_description prisms _exptl_crystal_colour black _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.393 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1468 _exptl_absorpt_coefficient_mu 0.691 _exptl_absorpt_correction_type analytical _exptl_absorpt_correction_T_min 0.77851 _exptl_absorpt_correction_T_max 0.91668 _exptl_absorpt_process_details 'N.W. Alcock (1970). Cryst. Computing, p271' _exptl_special_details ; ? ; _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 ; Oxford Diffraction Xcalibur CCD diffractometer ; _diffrn_measurement_method 'omega scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 16611 _diffrn_reflns_av_R_equivalents 0.0191 _diffrn_reflns_av_sigmaI/netI 0.0183 _diffrn_reflns_limit_h_min -32 _diffrn_reflns_limit_h_max 32 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 3.67 _diffrn_reflns_theta_max 27.00 _reflns_number_total 3678 _reflns_number_gt 3272 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlis CCD 170 (Oxford Diffraction, 2003) ; _computing_cell_refinement ; CrysAlis RED 170 (Oxford Diffraction, 2003) ; _computing_data_reduction ; CrysAlis RED 170 (Oxford Diffraction, 2003) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-3 (Farrugia, 1997)' _computing_publication_material ? _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. ; _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^)+(0.0529P)^2^+0.5860P] 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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3678 _refine_ls_number_parameters 231 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0315 _refine_ls_R_factor_gt 0.0275 _refine_ls_wR_factor_ref 0.0804 _refine_ls_wR_factor_gt 0.0794 _refine_ls_goodness_of_fit_ref 1.158 _refine_ls_restrained_S_all 1.158 _refine_ls_shift/su_max 0.000 _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 0.5000 0.70385(2) 0.7500 0.01445(9) Uani 1 2 d S . . O1 O 0.54957(4) 0.85144(11) 0.73627(7) 0.0206(2) Uani 1 1 d . . . N1 N 0.52931(5) 0.56520(12) 0.67754(8) 0.0150(2) Uani 1 1 d . . . C1 C 0.61093(6) 0.70653(15) 0.67773(10) 0.0171(3) Uani 1 1 d . . . C2 C 0.59450(6) 0.83568(16) 0.71340(10) 0.0185(3) Uani 1 1 d . . . C3 C 0.62923(7) 0.96204(17) 0.72271(11) 0.0246(3) Uani 1 1 d . . . H3 H 0.6186 1.0480 0.7450 0.030 Uiso 1 1 calc R . . C4 C 0.67681(7) 0.95864(18) 0.69983(11) 0.0277(4) Uani 1 1 d . . . H4 H 0.6978 1.0429 0.7057 0.033 Uiso 1 1 calc R . . C5 C 0.69573(7) 0.82965(19) 0.66692(11) 0.0258(3) Uani 1 1 d . . . C6 C 0.74650(7) 0.8272(2) 0.64576(13) 0.0360(4) Uani 1 1 d . . . H6 H 0.7675 0.9116 0.6530 0.043 Uiso 1 1 calc R . . C7 C 0.76531(7) 0.7035(2) 0.61495(13) 0.0392(5) Uani 1 1 d . . . H7 H 0.7986 0.7037 0.6006 0.047 Uiso 1 1 calc R . . C8 C 0.73380(7) 0.5765(2) 0.60527(12) 0.0339(4) Uani 1 1 d . . . H8 H 0.7463 0.4920 0.5843 0.041 Uiso 1 1 calc R . . C9 C 0.68461(6) 0.57462(19) 0.62622(11) 0.0262(3) Uani 1 1 d . . . H9 H 0.6649 0.4881 0.6203 0.031 Uiso 1 1 calc R . . C10 C 0.66327(6) 0.70109(17) 0.65653(10) 0.0202(3) Uani 1 1 d . . . C11 C 0.57515(6) 0.58392(15) 0.65617(9) 0.0163(3) Uani 1 1 d . . . H11 H 0.5856 0.5092 0.6234 0.020 Uiso 1 1 calc R . . C12 C 0.49954(6) 0.43362(14) 0.64679(9) 0.0157(3) Uani 1 1 d . . . C13 C 0.44239(6) 0.43956(15) 0.60459(10) 0.0166(3) Uani 1 1 d . . . C14 C 0.41392(7) 0.30812(15) 0.58156(11) 0.0220(3) Uani 1 1 d . . . H14 H 0.3760 0.3099 0.5536 0.026 Uiso 1 1 calc R . . C15 C 0.44074(7) 0.17539(16) 0.59939(11) 0.0263(4) Uani 1 1 d . . . H15 H 0.4208 0.0894 0.5840 0.032 Uiso 1 1 calc R . . C16 C 0.49706(7) 0.17065(16) 0.64004(11) 0.0242(3) Uani 1 1 d . . . H16 H 0.5152 0.0817 0.6514 0.029 Uiso 1 1 calc R . . C17 C 0.52638(6) 0.29943(15) 0.66378(10) 0.0198(3) Uani 1 1 d . . . H17 H 0.5643 0.2963 0.6913 0.024 Uiso 1 1 calc R . . C18 C 0.41135(6) 0.57848(15) 0.58100(10) 0.0171(3) Uani 1 1 d . . . C19 C 0.36128(6) 0.59619(17) 0.60088(10) 0.0220(3) Uani 1 1 d . . . H19 H 0.3493 0.5246 0.6340 0.026 Uiso 1 1 calc R . . C20 C 0.32912(7) 0.71922(18) 0.57192(11) 0.0271(3) Uani 1 1 d . . . H20 H 0.2961 0.7302 0.5863 0.033 Uiso 1 1 calc R . . C21 C 0.34622(7) 0.82570(17) 0.52155(11) 0.0282(4) Uani 1 1 d . . . H21 H 0.3244 0.9072 0.5010 0.034 Uiso 1 1 calc R . . C22 C 0.39605(7) 0.81025(16) 0.50184(11) 0.0246(3) Uani 1 1 d . . . H22 H 0.4076 0.8817 0.4681 0.030 Uiso 1 1 calc R . . C23 C 0.42876(6) 0.68856(15) 0.53226(10) 0.0190(3) Uani 1 1 d . . . H23 H 0.4625 0.6802 0.5201 0.023 Uiso 1 1 calc 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 Cu1 0.01512(14) 0.01072(12) 0.01929(14) 0.000 0.00779(10) 0.000 O1 0.0201(5) 0.0139(5) 0.0302(6) 0.0004(4) 0.0112(5) -0.0014(4) N1 0.0154(6) 0.0138(5) 0.0162(6) 0.0004(4) 0.0053(5) -0.0011(4) C1 0.0143(7) 0.0214(7) 0.0151(6) 0.0030(5) 0.0038(5) -0.0018(6) C2 0.0176(7) 0.0193(7) 0.0178(7) 0.0044(5) 0.0037(6) -0.0032(5) C3 0.0252(8) 0.0192(7) 0.0279(8) 0.0032(6) 0.0051(6) -0.0062(6) C4 0.0225(8) 0.0294(8) 0.0291(8) 0.0082(7) 0.0043(7) -0.0109(7) C5 0.0181(8) 0.0369(9) 0.0210(7) 0.0076(6) 0.0038(6) -0.0070(6) C6 0.0215(9) 0.0511(11) 0.0368(10) 0.0098(8) 0.0107(7) -0.0101(8) C7 0.0174(8) 0.0671(14) 0.0371(10) 0.0084(9) 0.0140(7) -0.0019(8) C8 0.0200(8) 0.0548(11) 0.0285(9) -0.0015(8) 0.0096(7) 0.0046(8) C9 0.0169(8) 0.0389(9) 0.0224(8) -0.0012(7) 0.0050(6) -0.0008(7) C10 0.0148(7) 0.0313(8) 0.0134(6) 0.0040(6) 0.0026(5) -0.0016(6) C11 0.0153(7) 0.0184(7) 0.0158(7) 0.0005(5) 0.0055(5) 0.0016(5) C12 0.0202(7) 0.0145(6) 0.0151(7) -0.0016(5) 0.0096(6) -0.0018(5) C13 0.0203(7) 0.0167(6) 0.0142(6) -0.0002(5) 0.0073(6) -0.0023(5) C14 0.0225(8) 0.0223(7) 0.0207(7) -0.0018(6) 0.0054(6) -0.0072(6) C15 0.0376(10) 0.0156(7) 0.0267(8) -0.0042(6) 0.0109(7) -0.0087(6) C16 0.0347(9) 0.0142(7) 0.0268(8) -0.0005(6) 0.0139(7) 0.0025(6) C17 0.0219(8) 0.0182(7) 0.0214(7) 0.0001(5) 0.0100(6) 0.0025(6) C18 0.0179(7) 0.0171(7) 0.0145(6) -0.0029(5) 0.0020(5) -0.0029(5) C19 0.0187(8) 0.0246(7) 0.0218(7) -0.0007(6) 0.0045(6) -0.0029(6) C20 0.0172(8) 0.0338(9) 0.0290(8) -0.0047(7) 0.0046(6) 0.0041(7) C21 0.0297(9) 0.0243(8) 0.0258(8) 0.0002(6) 0.0008(7) 0.0094(6) C22 0.0312(9) 0.0204(7) 0.0203(7) 0.0021(6) 0.0045(6) 0.0010(6) C23 0.0209(7) 0.0185(7) 0.0170(7) -0.0021(5) 0.0045(6) -0.0017(6) _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 O1 1.9016(10) . ? Cu1 O1 1.9016(10) 2_656 ? Cu1 N1 1.9638(11) . ? Cu1 N1 1.9638(11) 2_656 ? O1 C2 1.2918(18) . ? N1 C11 1.3056(18) . ? N1 C12 1.4301(17) . ? C1 C2 1.416(2) . ? C1 C11 1.4239(19) . ? C1 C10 1.454(2) . ? C2 C3 1.440(2) . ? C3 C4 1.349(2) . ? C3 H3 0.9300 . ? C4 C5 1.423(3) . ? C4 H4 0.9300 . ? C5 C6 1.414(2) . ? C5 C10 1.423(2) . ? C6 C7 1.367(3) . ? C6 H6 0.9300 . ? C7 C8 1.398(3) . ? C7 H7 0.9300 . ? C8 C9 1.374(2) . ? C8 H8 0.9300 . ? C9 C10 1.414(2) . ? C9 H9 0.9300 . ? C11 H11 0.9300 . ? C12 C17 1.3962(19) . ? C12 C13 1.404(2) . ? C13 C14 1.3987(19) . ? C13 C18 1.4880(19) . ? C14 C15 1.385(2) . ? C14 H14 0.9300 . ? C15 C16 1.381(3) . ? C15 H15 0.9300 . ? C16 C17 1.389(2) . ? C16 H16 0.9300 . ? C17 H17 0.9300 . ? C18 C19 1.397(2) . ? C18 C23 1.398(2) . ? C19 C20 1.389(2) . ? C19 H19 0.9300 . ? C20 C21 1.386(2) . ? C20 H20 0.9300 . ? C21 C22 1.387(2) . ? C21 H21 0.9300 . ? C22 C23 1.389(2) . ? C22 H22 0.9300 . ? C23 H23 0.9300 . ? 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 O1 Cu1 O1 88.95(6) . 2_656 ? O1 Cu1 N1 91.86(5) . . ? O1 Cu1 N1 153.37(5) 2_656 . ? O1 Cu1 N1 153.37(5) . 2_656 ? O1 Cu1 N1 91.86(5) 2_656 2_656 ? N1 Cu1 N1 99.05(7) . 2_656 ? C2 O1 Cu1 127.72(9) . . ? C11 N1 C12 117.01(12) . . ? C11 N1 Cu1 124.20(9) . . ? C12 N1 Cu1 118.78(9) . . ? C2 C1 C11 120.85(13) . . ? C2 C1 C10 120.10(13) . . ? C11 C1 C10 118.91(13) . . ? O1 C2 C1 125.21(13) . . ? O1 C2 C3 116.44(13) . . ? C1 C2 C3 118.32(13) . . ? C4 C3 C2 121.56(15) . . ? C4 C3 H3 119.2 . . ? C2 C3 H3 119.2 . . ? C3 C4 C5 121.82(15) . . ? C3 C4 H4 119.1 . . ? C5 C4 H4 119.1 . . ? C6 C5 C10 119.82(16) . . ? C6 C5 C4 120.96(16) . . ? C10 C5 C4 119.21(14) . . ? C7 C6 C5 121.42(17) . . ? C7 C6 H6 119.3 . . ? C5 C6 H6 119.3 . . ? C6 C7 C8 119.02(16) . . ? C6 C7 H7 120.5 . . ? C8 C7 H7 120.5 . . ? C9 C8 C7 121.07(17) . . ? C9 C8 H8 119.5 . . ? C7 C8 H8 119.5 . . ? C8 C9 C10 121.56(16) . . ? C8 C9 H9 119.2 . . ? C10 C9 H9 119.2 . . ? C9 C10 C5 117.09(15) . . ? C9 C10 C1 124.05(14) . . ? C5 C10 C1 118.86(14) . . ? N1 C11 C1 126.95(13) . . ? N1 C11 H11 116.5 . . ? C1 C11 H11 116.5 . . ? C17 C12 C13 120.08(13) . . ? C17 C12 N1 120.32(13) . . ? C13 C12 N1 119.47(12) . . ? C14 C13 C12 117.97(13) . . ? C14 C13 C18 118.90(13) . . ? C12 C13 C18 123.11(12) . . ? C15 C14 C13 121.62(15) . . ? C15 C14 H14 119.2 . . ? C13 C14 H14 119.2 . . ? C16 C15 C14 119.99(14) . . ? C16 C15 H15 120.0 . . ? C14 C15 H15 120.0 . . ? C15 C16 C17 119.65(14) . . ? C15 C16 H16 120.2 . . ? C17 C16 H16 120.2 . . ? C16 C17 C12 120.67(14) . . ? C16 C17 H17 119.7 . . ? C12 C17 H17 119.7 . . ? C19 C18 C23 118.43(13) . . ? C19 C18 C13 119.91(13) . . ? C23 C18 C13 121.46(13) . . ? C20 C19 C18 120.92(14) . . ? C20 C19 H19 119.5 . . ? C18 C19 H19 119.5 . . ? C21 C20 C19 120.00(15) . . ? C21 C20 H20 120.0 . . ? C19 C20 H20 120.0 . . ? C20 C21 C22 119.77(14) . . ? C20 C21 H21 120.1 . . ? C22 C21 H21 120.1 . . ? C21 C22 C23 120.29(15) . . ? C21 C22 H22 119.9 . . ? C23 C22 H22 119.9 . . ? C22 C23 C18 120.55(15) . . ? C22 C23 H23 119.7 . . ? C18 C23 H23 119.7 . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 27.00 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.374 _refine_diff_density_min -0.208 _refine_diff_density_rms 0.065 # Attachment '- Compound 3_Cincic.cif' data_Compound_3_Cincic&Kaitner _database_code_depnum_ccdc_archive 'CCDC 784720' #TrackingRef '- Compound 3_Cincic.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common bis[N-(2-biphenyl)-2-oxy-1-naphthaldiminato]cobalt(II) _chemical_melting_point ? _chemical_formula_moiety 'C46 H32 Co N2 O2' _chemical_formula_sum 'C46 H32 Co N2 O2' _chemical_formula_weight 703.67 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' _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+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 25.3808(13) _cell_length_b 8.8392(4) _cell_length_c 16.2656(10) _cell_angle_alpha 90.00 _cell_angle_beta 105.756(6) _cell_angle_gamma 90.00 _cell_volume 3512.0(3) _cell_formula_units_Z 4 _cell_measurement_temperature 293 _cell_measurement_reflns_used 2935 _cell_measurement_theta_min 5 _cell_measurement_theta_max 28 _exptl_crystal_description prisms _exptl_crystal_colour red _exptl_crystal_size_max 0.51 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.331 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1460 _exptl_absorpt_coefficient_mu 0.531 _exptl_absorpt_correction_type analytical _exptl_absorpt_correction_T_min 0.82268 _exptl_absorpt_correction_T_max 0.97049 _exptl_absorpt_process_details 'N.W. Alcock (1970). Cryst. Computing, p271' _exptl_special_details ; ? ; _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 ; Oxford Diffraction Xcalibur CCD diffractometer ; _diffrn_measurement_method 'omega scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 19239 _diffrn_reflns_av_R_equivalents 0.1050 _diffrn_reflns_av_sigmaI/netI 0.0706 _diffrn_reflns_limit_h_min -32 _diffrn_reflns_limit_h_max 32 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 3.74 _diffrn_reflns_theta_max 27.12 _reflns_number_total 3820 _reflns_number_gt 2622 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlis CCD 170 (Oxford Diffraction, 2003) ; _computing_cell_refinement ; CrysAlis RED 170 (Oxford Diffraction, 2003) ; _computing_data_reduction ; CrysAlis RED 170 (Oxford Diffraction, 2003) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-3 (Farrugia, 1997)' _computing_publication_material ? _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. ; _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^)+(0.0504P)^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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3820 _refine_ls_number_parameters 231 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0685 _refine_ls_R_factor_gt 0.0409 _refine_ls_wR_factor_ref 0.1039 _refine_ls_wR_factor_gt 0.0979 _refine_ls_goodness_of_fit_ref 0.908 _refine_ls_restrained_S_all 0.908 _refine_ls_shift/su_max 0.000 _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 Co1 Co 0.5000 0.72069(4) 0.7500 0.03815(14) Uani 1 2 d S . . O1 O 0.56062(6) 0.85566(16) 0.76823(9) 0.0452(4) Uani 1 1 d . . . N1 N 0.52906(6) 0.58608(18) 0.67456(9) 0.0347(4) Uani 1 1 d . . . C1 C 0.61374(8) 0.7300(2) 0.68687(11) 0.0378(5) Uani 1 1 d . . . C2 C 0.60248(8) 0.8498(2) 0.73684(13) 0.0414(5) Uani 1 1 d . . . C3 C 0.63876(9) 0.9776(3) 0.75395(15) 0.0532(6) Uani 1 1 d . . . H3 H 0.6310 1.0585 0.7853 0.064 Uiso 1 1 calc R . . C4 C 0.68381(9) 0.9825(3) 0.72540(15) 0.0586(7) Uani 1 1 d . . . H4 H 0.7058 1.0683 0.7360 0.070 Uiso 1 1 calc R . . C5 C 0.69869(9) 0.8608(3) 0.67964(13) 0.0498(6) Uani 1 1 d . . . C6 C 0.74803(10) 0.8661(3) 0.65410(15) 0.0642(7) Uani 1 1 d . . . H6 H 0.7705 0.9507 0.6674 0.077 Uiso 1 1 calc R . . C7 C 0.76273(10) 0.7499(3) 0.61073(16) 0.0682(8) Uani 1 1 d . . . H7 H 0.7949 0.7553 0.5938 0.082 Uiso 1 1 calc R . . C8 C 0.72970(10) 0.6231(3) 0.59171(15) 0.0633(7) Uani 1 1 d . . . H8 H 0.7400 0.5430 0.5623 0.076 Uiso 1 1 calc R . . C9 C 0.68171(9) 0.6140(3) 0.61577(13) 0.0519(6) Uani 1 1 d . . . H9 H 0.6602 0.5275 0.6023 0.062 Uiso 1 1 calc R . . C10 C 0.66448(8) 0.7323(3) 0.66010(11) 0.0420(5) Uani 1 1 d . . . C11 C 0.57713(8) 0.6063(2) 0.66056(12) 0.0388(5) Uani 1 1 d . . . H11 H 0.5887 0.5306 0.6297 0.047 Uiso 1 1 calc R . . C12 C 0.50287(8) 0.4450(2) 0.64693(11) 0.0360(5) Uani 1 1 d . . . C13 C 0.44716(8) 0.4421(2) 0.60183(12) 0.0392(5) Uani 1 1 d . . . C14 C 0.42266(10) 0.3008(3) 0.58130(14) 0.0527(6) Uani 1 1 d . . . H14 H 0.3859 0.2962 0.5509 0.063 Uiso 1 1 calc R . . C15 C 0.45114(11) 0.1682(3) 0.60458(15) 0.0580(6) Uani 1 1 d . . . H15 H 0.4336 0.0756 0.5904 0.070 Uiso 1 1 calc R . . C16 C 0.50523(11) 0.1729(3) 0.64866(15) 0.0555(6) Uani 1 1 d . . . H16 H 0.5247 0.0836 0.6643 0.067 Uiso 1 1 calc R . . C17 C 0.53080(9) 0.3108(2) 0.66990(13) 0.0464(5) Uani 1 1 d . . . H17 H 0.5676 0.3133 0.7003 0.056 Uiso 1 1 calc R . . C18 C 0.41425(8) 0.5810(2) 0.57349(12) 0.0415(5) Uani 1 1 d . . . C19 C 0.36392(9) 0.5987(3) 0.59201(14) 0.0535(6) Uani 1 1 d . . . H19 H 0.3529 0.5271 0.6258 0.064 Uiso 1 1 calc R . . C20 C 0.33030(11) 0.7206(3) 0.56107(18) 0.0698(7) Uani 1 1 d . . . H20 H 0.2971 0.7313 0.5743 0.084 Uiso 1 1 calc R . . C21 C 0.34623(12) 0.8254(3) 0.51073(17) 0.0718(8) Uani 1 1 d . . . H21 H 0.3235 0.9071 0.4893 0.086 Uiso 1 1 calc R . . C22 C 0.39562(12) 0.8109(3) 0.49151(15) 0.0646(7) Uani 1 1 d . . . H22 H 0.4060 0.8823 0.4568 0.078 Uiso 1 1 calc R . . C23 C 0.42975(9) 0.6911(3) 0.52343(12) 0.0481(6) Uani 1 1 d . . . H23 H 0.4635 0.6837 0.5114 0.058 Uiso 1 1 calc 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 Co1 0.0339(2) 0.0349(2) 0.0486(2) 0.000 0.01622(17) 0.000 O1 0.0379(8) 0.0417(9) 0.0598(9) -0.0091(7) 0.0200(7) -0.0075(7) N1 0.0305(9) 0.0356(10) 0.0385(9) -0.0011(7) 0.0100(7) -0.0039(7) C1 0.0307(10) 0.0449(13) 0.0370(10) 0.0012(9) 0.0075(8) -0.0046(9) C2 0.0361(11) 0.0421(13) 0.0447(11) 0.0024(10) 0.0088(9) -0.0042(10) C3 0.0493(14) 0.0477(15) 0.0631(14) -0.0090(11) 0.0162(11) -0.0143(11) C4 0.0500(15) 0.0614(17) 0.0642(15) -0.0011(12) 0.0150(12) -0.0232(13) C5 0.0387(12) 0.0648(17) 0.0454(12) 0.0060(11) 0.0105(10) -0.0106(11) C6 0.0422(14) 0.090(2) 0.0617(15) 0.0095(14) 0.0165(12) -0.0207(14) C7 0.0396(13) 0.111(3) 0.0598(15) 0.0092(15) 0.0229(12) -0.0033(14) C8 0.0433(14) 0.092(2) 0.0572(15) -0.0069(13) 0.0186(12) 0.0027(14) C9 0.0369(12) 0.0720(17) 0.0481(13) -0.0047(11) 0.0141(10) -0.0031(11) C10 0.0312(11) 0.0606(15) 0.0328(10) 0.0036(10) 0.0062(8) -0.0039(10) C11 0.0363(11) 0.0439(13) 0.0367(11) -0.0025(9) 0.0110(9) 0.0019(9) C12 0.0396(11) 0.0372(12) 0.0343(10) -0.0024(8) 0.0154(9) -0.0053(9) C13 0.0405(12) 0.0405(13) 0.0386(11) -0.0029(9) 0.0140(9) -0.0073(9) C14 0.0490(14) 0.0553(17) 0.0528(13) -0.0054(11) 0.0122(11) -0.0170(12) C15 0.0771(18) 0.0374(13) 0.0618(14) -0.0053(11) 0.0225(13) -0.0153(13) C16 0.0700(17) 0.0375(13) 0.0613(14) 0.0025(11) 0.0216(13) 0.0036(12) C17 0.0473(13) 0.0441(14) 0.0499(12) -0.0007(10) 0.0168(10) 0.0010(10) C18 0.0393(12) 0.0456(13) 0.0365(11) -0.0061(9) 0.0052(9) -0.0091(10) C19 0.0412(13) 0.0564(16) 0.0617(14) -0.0027(12) 0.0118(11) -0.0073(11) C20 0.0437(14) 0.083(2) 0.0788(17) -0.0089(16) 0.0100(13) 0.0092(15) C21 0.0629(18) 0.0669(19) 0.0741(18) -0.0015(15) -0.0012(14) 0.0228(15) C22 0.0781(19) 0.0596(18) 0.0501(13) 0.0080(12) 0.0071(13) 0.0034(14) C23 0.0504(14) 0.0520(15) 0.0407(11) -0.0010(10) 0.0105(10) -0.0016(11) _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 Co1 O1 1.9055(14) 2_656 ? Co1 O1 1.9055(14) . ? Co1 N1 1.9893(16) 2_656 ? Co1 N1 1.9893(15) . ? O1 C2 1.299(2) . ? N1 C11 1.313(2) . ? N1 C12 1.427(2) . ? C1 C2 1.411(3) . ? C1 C11 1.423(3) . ? C1 C10 1.467(3) . ? C2 C3 1.436(3) . ? C3 C4 1.347(3) . ? C3 H3 0.9300 . ? C4 C5 1.417(3) . ? C4 H4 0.9300 . ? C5 C10 1.412(3) . ? C5 C6 1.423(3) . ? C6 C7 1.355(3) . ? C6 H6 0.9300 . ? C7 C8 1.384(3) . ? C7 H7 0.9300 . ? C8 C9 1.379(3) . ? C8 H8 0.9300 . ? C9 C10 1.406(3) . ? C9 H9 0.9300 . ? C11 H11 0.9300 . ? C12 C17 1.380(3) . ? C12 C13 1.405(3) . ? C13 C14 1.395(3) . ? C13 C18 1.486(3) . ? C14 C15 1.375(3) . ? C14 H14 0.9300 . ? C15 C16 1.366(3) . ? C15 H15 0.9300 . ? C16 C17 1.380(3) . ? C16 H16 0.9300 . ? C17 H17 0.9300 . ? C18 C23 1.392(3) . ? C18 C19 1.399(3) . ? C19 C20 1.381(3) . ? C19 H19 0.9300 . ? C20 C21 1.368(4) . ? C20 H20 0.9300 . ? C21 C22 1.378(4) . ? C21 H21 0.9300 . ? C22 C23 1.377(3) . ? C22 H22 0.9300 . ? C23 H23 0.9300 . ? 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 O1 Co1 O1 102.48(9) 2_656 . ? O1 Co1 N1 92.95(6) 2_656 2_656 ? O1 Co1 N1 134.23(6) . 2_656 ? O1 Co1 N1 134.23(6) 2_656 . ? O1 Co1 N1 92.95(6) . . ? N1 Co1 N1 106.53(9) 2_656 . ? C2 O1 Co1 128.77(13) . . ? C11 N1 C12 116.08(16) . . ? C11 N1 Co1 122.91(13) . . ? C12 N1 Co1 119.86(12) . . ? C2 C1 C11 122.14(18) . . ? C2 C1 C10 119.45(18) . . ? C11 C1 C10 118.40(18) . . ? O1 C2 C1 124.85(19) . . ? O1 C2 C3 116.3(2) . . ? C1 C2 C3 118.86(19) . . ? C4 C3 C2 121.2(2) . . ? C4 C3 H3 119.4 . . ? C2 C3 H3 119.4 . . ? C3 C4 C5 122.0(2) . . ? C3 C4 H4 119.0 . . ? C5 C4 H4 119.0 . . ? C10 C5 C4 119.6(2) . . ? C10 C5 C6 119.8(2) . . ? C4 C5 C6 120.6(2) . . ? C7 C6 C5 121.0(2) . . ? C7 C6 H6 119.5 . . ? C5 C6 H6 119.5 . . ? C6 C7 C8 119.7(2) . . ? C6 C7 H7 120.2 . . ? C8 C7 H7 120.2 . . ? C9 C8 C7 120.8(2) . . ? C9 C8 H8 119.6 . . ? C7 C8 H8 119.6 . . ? C8 C9 C10 121.6(2) . . ? C8 C9 H9 119.2 . . ? C10 C9 H9 119.2 . . ? C9 C10 C5 117.11(19) . . ? C9 C10 C1 124.20(19) . . ? C5 C10 C1 118.7(2) . . ? N1 C11 C1 127.89(19) . . ? N1 C11 H11 116.1 . . ? C1 C11 H11 116.1 . . ? C17 C12 C13 119.72(19) . . ? C17 C12 N1 120.32(18) . . ? C13 C12 N1 119.77(18) . . ? C14 C13 C12 117.5(2) . . ? C14 C13 C18 119.28(19) . . ? C12 C13 C18 123.25(18) . . ? C15 C14 C13 122.0(2) . . ? C15 C14 H14 119.0 . . ? C13 C14 H14 119.0 . . ? C16 C15 C14 119.8(2) . . ? C16 C15 H15 120.1 . . ? C14 C15 H15 120.1 . . ? C15 C16 C17 119.7(2) . . ? C15 C16 H16 120.1 . . ? C17 C16 H16 120.1 . . ? C16 C17 C12 121.3(2) . . ? C16 C17 H17 119.4 . . ? C12 C17 H17 119.4 . . ? C23 C18 C19 117.9(2) . . ? C23 C18 C13 122.31(19) . . ? C19 C18 C13 119.66(19) . . ? C20 C19 C18 121.2(2) . . ? C20 C19 H19 119.4 . . ? C18 C19 H19 119.4 . . ? C21 C20 C19 119.5(3) . . ? C21 C20 H20 120.2 . . ? C19 C20 H20 120.2 . . ? C20 C21 C22 120.5(2) . . ? C20 C21 H21 119.8 . . ? C22 C21 H21 119.8 . . ? C23 C22 C21 120.3(2) . . ? C23 C22 H22 119.9 . . ? C21 C22 H22 119.9 . . ? C22 C23 C18 120.6(2) . . ? C22 C23 H23 119.7 . . ? C18 C23 H23 119.7 . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 27.00 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.512 _refine_diff_density_min -0.266 _refine_diff_density_rms 0.056