Electronic Supplementary Material for CrystEngComm This journal is (c) The Royal Society of Chemistry 2006 data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 _publ_contact_author_name 'Berta Covelo' _publ_contact_author_address ; Departamento de Quimica Inorganica Facultade de Quimica Edificio de Ciencias Experimentais Universidade de Vigo 36310 Vigo Galicia, Spain ; _publ_contact_author_email bcovelo@uvigo.es _publ_contact_author_fax '0034 86 812556' _publ_contact_author_phone '0034 86 812273' _publ_contact_letter ; Please consider this CIF submission as supplementary material of article to be submitted to CrystEngComm ; #=============================================================================== # 2. TITLE AND AUTHOR LIST _publ_section_title ; Supramolecular architecture of neutral and cationic complexes of transition metals with lactate and 1,10-phenathroline. ; loop_ _publ_author_name _publ_author_address R.Carballo ; Departamento de Quimica Inorganica Facultade de Quimica Edificio de Ciencias Experimentais Universidade de Vigo 36310-Vigo, Galicia Spain ; E.M.Vazquez-Lopez ; Departamento de Quimica Inorganica Facultade de Quimica Edificio de Ciencias Experimentais Universidade de Vigo 36310-Vigo, Galicia Spain ; B.Covelo ; Departamento de Quimica Inorganica Facultade de Quimica Edificio de Ciencias Experimentais Universidade de Vigo 36310-Vigo, Galicia Spain ; E.Garcia-Martinez ; Departamento de Quimica Inorg`'anica Facultade de Quimica Edificio de Ciencias Experimentais Universidade de Vigo 36310-Vigo, Galicia Spain ; ; A.Castineiras ; ; Departamento de Quimica Inorganica Facultade de Farmacia Universidade de Santiago de Compostela 15706-Santiago de Compostela, Galicia Spain ; S.Balboa ; Departamento de Quimica Inorganica Facultade de Farmacia Universidade de Santiago de Compostela 15706-Santiago de Compostela, Galicia Spain ; J.Niclos ; Departamento de Quimica Inorganica Facultad de Farmacia Universidad de Granada E-18071 Granada Spain ; #=================================================================== data_cold2_colphen _database_code_depnum_ccdc_archive 'CCDC 288312' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H22 Co N2 O8' _chemical_formula_weight 453.31 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 Orthorhombic _symmetry_space_group_name_H-M Fdd2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z' 'x+1/4, -y+1/4, z+1/4' '-x+1/4, y+1/4, z+1/4' 'x, y+1/2, z+1/2' '-x, -y+1/2, z+1/2' 'x+1/4, -y+3/4, z+3/4' '-x+1/4, y+3/4, z+3/4' 'x+1/2, y, z+1/2' '-x+1/2, -y, z+1/2' 'x+3/4, -y+1/4, z+3/4' '-x+3/4, y+1/4, z+3/4' 'x+1/2, y+1/2, z' '-x+1/2, -y+1/2, z' 'x+3/4, -y+3/4, z+1/4' '-x+3/4, y+3/4, z+1/4' _cell_length_a 13.1537(15) _cell_length_b 28.617(3) _cell_length_c 10.3650(11) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3901.6(7) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prism _exptl_crystal_colour orange _exptl_crystal_size_max .30 _exptl_crystal_size_mid .14 _exptl_crystal_size_min .08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.543 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1880 _exptl_absorpt_coefficient_mu 0.929 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7752 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5846 _diffrn_reflns_av_R_equivalents 0.0565 _diffrn_reflns_av_sigmaI/netI 0.0902 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -37 _diffrn_reflns_limit_k_max 33 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 7 _diffrn_reflns_theta_min 2.60 _diffrn_reflns_theta_max 28.05 _reflns_number_total 1965 _reflns_number_gt 1122 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _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. ; _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^)+(0.0234P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _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 0.07(2) _refine_ls_number_reflns 1965 _refine_ls_number_parameters 139 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.1026 _refine_ls_R_factor_gt 0.0432 _refine_ls_wR_factor_ref 0.0747 _refine_ls_wR_factor_gt 0.0642 _refine_ls_goodness_of_fit_ref 0.856 _refine_ls_restrained_S_all 0.857 _refine_ls_shift/su_max 0.003 _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 Co Co 0.2500 0.2500 0.03810(8) 0.0530(2) Uani 1 2 d S . . O11 O 0.2090(3) 0.30090(11) 0.1660(3) 0.0631(10) Uani 1 1 d . . . O12 O 0.0886(3) 0.32761(9) 0.2939(4) 0.0790(9) Uani 1 1 d . . . O13 O 0.0944(2) 0.23692(10) 0.0645(3) 0.0591(9) Uani 1 1 d D . . H13 H 0.066(3) 0.2102(10) 0.047(5) 0.105(19) Uiso 1 1 d D . . C11 C 0.1219(4) 0.29867(15) 0.2141(4) 0.0558(13) Uani 1 1 d . . . C12 C 0.0501(4) 0.25820(14) 0.1770(4) 0.0611(13) Uani 1 1 d . . . H12 H -0.0162 0.2712 0.1536 0.073 Uiso 1 1 calc R . . C13 C 0.0358(3) 0.22432(14) 0.2858(6) 0.0844(16) Uani 1 1 d . . . H13A H -0.0099 0.2000 0.2594 0.127 Uiso 1 1 calc R . . H13B H 0.0079 0.2404 0.3591 0.127 Uiso 1 1 calc R . . H13C H 0.1003 0.2109 0.3087 0.127 Uiso 1 1 calc R . . N1 N 0.2599(3) 0.20389(15) -0.1222(3) 0.0538(12) Uani 1 1 d . . . C1 C 0.2700(4) 0.15760(16) -0.1226(4) 0.0611(14) Uani 1 1 d . . . H1 H 0.2714 0.1423 -0.0435 0.073 Uiso 1 1 calc R . . C2 C 0.2785(4) 0.13107(16) -0.2327(5) 0.0720(14) Uani 1 1 d . . . H2 H 0.2867 0.0988 -0.2272 0.086 Uiso 1 1 calc R . . C3 C 0.2749(4) 0.15252(17) -0.3500(5) 0.0716(16) Uani 1 1 d . . . H3 H 0.2808 0.1349 -0.4251 0.086 Uiso 1 1 calc R . . C4 C 0.2621(4) 0.20121(15) -0.3574(5) 0.0570(13) Uani 1 1 d . . . C5 C 0.2561(3) 0.22501(12) -0.2396(4) 0.0453(10) Uani 1 1 d . . . C6 C 0.2559(5) 0.22659(13) -0.4741(6) 0.0718(13) Uani 1 1 d . . . H6 H 0.2601 0.2107 -0.5523 0.086 Uiso 1 1 calc R . . O1 O 0.2331(2) 0.40365(10) 0.2728(4) 0.0783(10) Uani 1 1 d . . . H1W H 0.2767 0.4069 0.1939 0.096(18) Uiso 1 1 d . . . H2W H 0.2066 0.3719 0.2654 0.13(2) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Co 0.0719(6) 0.0429(4) 0.0442(5) 0.000 0.000 -0.0064(6) O11 0.079(3) 0.0439(19) 0.066(3) -0.0141(17) 0.012(2) -0.009(2) O12 0.116(3) 0.0473(17) 0.074(2) -0.0108(19) 0.012(2) 0.0103(17) O13 0.080(2) 0.055(2) 0.042(2) -0.0086(15) 0.0030(16) -0.0120(17) C11 0.086(4) 0.040(3) 0.041(3) 0.007(2) -0.002(3) 0.007(3) C12 0.076(4) 0.051(3) 0.057(3) 0.001(2) 0.003(2) 0.006(3) C13 0.118(5) 0.071(3) 0.065(3) 0.005(4) 0.005(5) -0.008(3) N1 0.067(3) 0.048(3) 0.047(3) 0.0048(19) 0.003(2) -0.005(2) C1 0.078(4) 0.050(3) 0.055(3) 0.003(2) 0.007(3) -0.007(3) C2 0.107(4) 0.045(3) 0.064(4) -0.014(3) 0.011(3) -0.001(3) C3 0.085(4) 0.068(3) 0.062(3) -0.025(3) 0.009(3) -0.002(3) C4 0.067(4) 0.054(3) 0.050(3) -0.010(2) 0.002(3) -0.001(3) C5 0.048(3) 0.052(2) 0.036(3) -0.0041(19) -0.001(2) -0.005(2) C6 0.090(4) 0.086(3) 0.039(3) -0.001(4) -0.004(3) 0.008(4) O1 0.100(3) 0.0477(19) 0.087(3) -0.0132(17) 0.014(3) 0.0011(17) _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 Co O11 2.042(3) 14 ? Co O11 2.042(3) . ? Co O13 2.098(3) 14 ? Co O13 2.098(3) . ? Co N1 2.126(4) . ? Co N1 2.126(4) 14 ? O11 C11 1.252(6) . ? O12 C11 1.249(5) . ? O13 C12 1.439(5) . ? C11 C12 1.543(6) . ? C12 C13 1.499(6) . ? N1 C1 1.331(6) . ? N1 C5 1.359(4) . ? C1 C2 1.375(6) . ? C2 C3 1.363(6) . ? C3 C4 1.406(5) . ? C4 C5 1.401(5) . ? C4 C6 1.413(6) . ? C5 C5 1.439(7) 14 ? C6 C6 1.349(7) 14 ? 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 O11 Co O11 99.0(2) 14 . ? O11 Co O13 77.60(14) 14 14 ? O11 Co O13 92.61(13) . 14 ? O11 Co O13 92.61(13) 14 . ? O11 Co O13 77.60(14) . . ? O13 Co O13 165.02(17) 14 . ? O11 Co N1 92.78(12) 14 . ? O11 Co N1 165.11(17) . . ? O13 Co N1 98.79(13) 14 . ? O13 Co N1 92.92(13) . . ? O11 Co N1 165.11(17) 14 14 ? O11 Co N1 92.78(12) . 14 ? O13 Co N1 92.92(13) 14 14 ? O13 Co N1 98.79(13) . 14 ? N1 Co N1 77.2(2) . 14 ? C11 O11 Co 117.6(3) . . ? C12 O13 Co 115.2(3) . . ? O12 C11 O11 123.4(5) . . ? O12 C11 C12 116.6(5) . . ? O11 C11 C12 120.0(4) . . ? O13 C12 C13 112.8(3) . . ? O13 C12 C11 105.8(4) . . ? C13 C12 C11 112.0(4) . . ? C1 N1 C5 116.3(4) . . ? C1 N1 Co 128.8(3) . . ? C5 N1 Co 114.9(3) . . ? N1 C1 C2 124.1(4) . . ? C3 C2 C1 119.2(4) . . ? C2 C3 C4 120.0(5) . . ? C5 C4 C3 116.2(4) . . ? C5 C4 C6 119.5(4) . . ? C3 C4 C6 124.3(4) . . ? N1 C5 C4 124.2(4) . . ? N1 C5 C5 116.5(2) . 14 ? C4 C5 C5 119.3(2) . 14 ? C6 C6 C4 121.1(3) 14 . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O13 H13 O1 0.868(19) 1.76(2) 2.628(4) 175(5) 8_544 O1 H1W O12 1.00 1.81 2.800(5) 168 7_554 O1 H2W O12 0.98 2.02 2.898(4) 148 . O1 H2W O11 0.98 2.28 3.158(4) 149 . C1 H1 O12 0.93 2.52 3.203(5) 130.8 8_544 _diffrn_measured_fraction_theta_max 0.986 _diffrn_reflns_theta_full 28.05 _diffrn_measured_fraction_theta_full 0.986 _refine_diff_density_max 0.522 _refine_diff_density_min -0.250 _refine_diff_density_rms 0.045 #======================================================================== data_culd_culphen _database_code_depnum_ccdc_archive 'CCDC 288313' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H22 Cu N2 O8' _chemical_formula_weight 457.92 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 Orthorhombic _symmetry_space_group_name_H-M Fdd2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z' 'x+1/4, -y+1/4, z+1/4' '-x+1/4, y+1/4, z+1/4' 'x, y+1/2, z+1/2' '-x, -y+1/2, z+1/2' 'x+1/4, -y+3/4, z+3/4' '-x+1/4, y+3/4, z+3/4' 'x+1/2, y, z+1/2' '-x+1/2, -y, z+1/2' 'x+3/4, -y+1/4, z+3/4' '-x+3/4, y+1/4, z+3/4' 'x+1/2, y+1/2, z' '-x+1/2, -y+1/2, z' 'x+3/4, -y+3/4, z+1/4' '-x+3/4, y+3/4, z+1/4' _cell_length_a 12.6879(12) _cell_length_b 27.985(3) _cell_length_c 10.8363(11) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3847.7(7) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prism _exptl_crystal_colour blue _exptl_crystal_size_max .23 _exptl_crystal_size_mid .14 _exptl_crystal_size_min .13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.581 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1896 _exptl_absorpt_coefficient_mu 1.185 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8128 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5975 _diffrn_reflns_av_R_equivalents 0.0487 _diffrn_reflns_av_sigmaI/netI 0.0756 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -36 _diffrn_reflns_limit_k_max 34 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.58 _diffrn_reflns_theta_max 27.96 _reflns_number_total 2024 _reflns_number_gt 1449 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _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. ; _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^)+(0.0229P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _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 0.020(19) _refine_ls_number_reflns 2024 _refine_ls_number_parameters 145 _refine_ls_number_restraints 4 _refine_ls_R_factor_all 0.0666 _refine_ls_R_factor_gt 0.0404 _refine_ls_wR_factor_ref 0.0681 _refine_ls_wR_factor_gt 0.0628 _refine_ls_goodness_of_fit_ref 0.883 _refine_ls_restrained_S_all 0.885 _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 Cu Cu 0.2500 0.2500 0.03214(5) 0.03684(17) Uani 1 2 d S . . O11 O 0.2194(2) 0.30005(11) 0.1550(3) 0.0410(7) Uani 1 1 d . . . O12 O 0.1195(2) 0.32832(8) 0.3042(3) 0.0528(7) Uani 1 1 d . . . O13 O 0.0700(2) 0.24391(10) 0.0715(2) 0.0454(7) Uani 1 1 d D . . H13 H 0.046(3) 0.2195(11) 0.037(4) 0.087(17) Uiso 1 1 d D . . C11 C 0.1367(3) 0.29930(12) 0.2183(3) 0.0354(9) Uani 1 1 d . . . C12 C 0.0513(3) 0.26169(13) 0.1908(3) 0.0394(9) Uani 1 1 d . . . H12 H -0.0171 0.2779 0.1903 0.047 Uiso 1 1 calc R . . C13 C 0.0483(3) 0.22344(12) 0.2900(4) 0.0471(10) Uani 1 1 d . . . H13A H 0.0015 0.1983 0.2650 0.071 Uiso 1 1 calc R . . H13B H 0.0237 0.2371 0.3659 0.071 Uiso 1 1 calc R . . H13C H 0.1178 0.2107 0.3017 0.071 Uiso 1 1 calc R . . N1 N 0.2588(2) 0.20320(15) -0.1086(3) 0.0345(9) Uani 1 1 d . . . C1 C 0.2668(3) 0.15596(14) -0.1070(4) 0.0441(10) Uani 1 1 d . . . H1 H 0.2688 0.1406 -0.0309 0.053 Uiso 1 1 calc R . . C2 C 0.2724(3) 0.12826(13) -0.2137(4) 0.0468(9) Uani 1 1 d . . . H2 H 0.2775 0.0952 -0.2081 0.056 Uiso 1 1 calc R . . C3 C 0.2703(3) 0.14977(14) -0.3248(4) 0.0484(11) Uani 1 1 d . . . H3 H 0.2755 0.1316 -0.3964 0.058 Uiso 1 1 calc R . . C4 C 0.2603(3) 0.19981(13) -0.3330(3) 0.0392(9) Uani 1 1 d . . . C5 C 0.2555(2) 0.22429(11) -0.2214(3) 0.0342(8) Uani 1 1 d . . . C6 C 0.2557(4) 0.22559(13) -0.4464(4) 0.0512(11) Uani 1 1 d . . . H6 H 0.2605 0.2092 -0.5209 0.061 Uiso 1 1 calc R . . O1 O 0.2579(3) 0.40686(12) 0.2762(3) 0.0618(8) Uani 1 1 d D . . H1W H 0.292(3) 0.4112(14) 0.204(2) 0.060(14) Uiso 1 1 d D . . H2W H 0.209(4) 0.3863(19) 0.257(6) 0.16(3) Uiso 1 1 d 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 Cu 0.0471(3) 0.0319(3) 0.0316(3) 0.000 0.000 -0.0014(5) O11 0.0498(15) 0.0329(17) 0.0402(18) -0.0050(13) 0.0061(14) -0.0024(15) O12 0.0770(19) 0.0354(15) 0.0458(16) -0.0103(14) 0.0144(15) 0.0020(13) O13 0.0582(16) 0.0452(17) 0.0328(17) -0.0024(15) -0.0073(11) -0.0113(15) C11 0.047(2) 0.028(2) 0.032(2) 0.0048(17) -0.0036(19) 0.0081(18) C12 0.040(2) 0.040(2) 0.039(2) 0.0044(18) 0.0048(18) 0.0016(18) C13 0.058(2) 0.039(2) 0.044(2) 0.009(2) 0.010(3) -0.0026(17) N1 0.0383(18) 0.032(2) 0.0328(19) 0.0031(15) -0.0010(16) -0.0050(17) C1 0.050(3) 0.037(2) 0.046(2) 0.0067(19) 0.002(2) 0.000(2) C2 0.062(2) 0.027(2) 0.052(2) -0.006(2) 0.005(3) 0.0035(18) C3 0.055(3) 0.044(2) 0.047(3) -0.014(2) 0.002(2) -0.004(2) C4 0.042(2) 0.035(2) 0.040(2) -0.0095(17) 0.003(2) 0.004(2) C5 0.0290(16) 0.0351(19) 0.038(2) 0.0013(17) 0.005(3) 0.0005(15) C6 0.057(2) 0.063(2) 0.034(3) -0.015(2) 0.000(2) 0.009(3) O1 0.072(2) 0.0476(19) 0.066(2) -0.0163(17) 0.021(2) -0.0066(16) _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 Cu O11 1.971(3) . ? Cu O11 1.971(3) 14 ? Cu N1 2.013(4) . ? Cu N1 2.013(4) 14 ? Cu O13 2.330(3) 14 ? Cu O13 2.330(3) . ? O11 C11 1.253(4) . ? O12 C11 1.254(4) . ? O13 C12 1.405(4) . ? C11 C12 1.540(5) . ? C12 C13 1.517(5) . ? N1 C1 1.326(5) . ? N1 C5 1.358(5) . ? C1 C2 1.394(6) . ? C2 C3 1.347(6) . ? C3 C4 1.409(5) . ? C4 C5 1.392(5) . ? C4 C6 1.426(5) . ? C5 C5 1.445(6) 14 ? C6 C6 1.374(7) 14 ? 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 O11 Cu O11 95.02(17) . 14 ? O11 Cu N1 170.00(14) . . ? O11 Cu N1 92.20(10) 14 . ? O11 Cu N1 92.20(10) . 14 ? O11 Cu N1 170.00(14) 14 14 ? N1 Cu N1 81.5(2) . 14 ? O11 Cu O13 91.00(10) . 14 ? O11 Cu O13 74.63(11) 14 14 ? N1 Cu O13 97.58(10) . 14 ? N1 Cu O13 98.38(11) 14 14 ? O11 Cu O13 74.63(11) . . ? O11 Cu O13 91.00(10) 14 . ? N1 Cu O13 98.38(10) . . ? N1 Cu O13 97.58(10) 14 . ? O13 Cu O13 158.88(12) 14 . ? C11 O11 Cu 121.5(3) . . ? C12 O13 Cu 107.9(2) . . ? O11 C11 O12 122.7(4) . . ? O11 C11 C12 119.6(3) . . ? O12 C11 C12 117.6(3) . . ? O13 C12 C13 113.9(3) . . ? O13 C12 C11 107.5(3) . . ? C13 C12 C11 111.3(3) . . ? C1 N1 C5 116.6(4) . . ? C1 N1 Cu 130.0(3) . . ? C5 N1 Cu 113.4(3) . . ? N1 C1 C2 123.2(4) . . ? C3 C2 C1 119.5(3) . . ? C2 C3 C4 120.1(4) . . ? C5 C4 C3 116.0(3) . . ? C5 C4 C6 119.9(3) . . ? C3 C4 C6 124.1(3) . . ? N1 C5 C4 124.5(3) . . ? N1 C5 C5 115.8(2) . 14 ? C4 C5 C5 119.6(2) . 14 ? C6 C6 C4 120.5(2) 14 . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O13 H13 O1 0.834(19) 1.89(3) 2.674(4) 157(5) 8_544 O1 H1W O12 0.904(19) 1.92(2) 2.823(4) 177(4) 7_554 O1 H2W O12 0.87(2) 2.04(4) 2.829(4) 149(6) . C1 H1 O12 0.93 2.64 3.281(5) 126.7 8_544 _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 27.96 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.591 _refine_diff_density_min -0.256 _refine_diff_density_rms 0.052 #====================================================================== data_znld_znlphen _database_code_depnum_ccdc_archive 'CCDC 288314' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H22 N2 O8 Zn' _chemical_formula_weight 459.75 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' Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Fdd2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z' 'x+1/4, -y+1/4, z+1/4' '-x+1/4, y+1/4, z+1/4' 'x, y+1/2, z+1/2' '-x, -y+1/2, z+1/2' 'x+1/4, -y+3/4, z+3/4' '-x+1/4, y+3/4, z+3/4' 'x+1/2, y, z+1/2' '-x+1/2, -y, z+1/2' 'x+3/4, -y+1/4, z+3/4' '-x+3/4, y+1/4, z+3/4' 'x+1/2, y+1/2, z' '-x+1/2, -y+1/2, z' 'x+3/4, -y+3/4, z+1/4' '-x+3/4, y+3/4, z+1/4' _cell_length_a 12.880(3) _cell_length_b 28.401(6) _cell_length_c 10.376(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3795.6(14) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.16 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.609 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1904 _exptl_absorpt_coefficient_mu 1.345 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5836 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5531 _diffrn_reflns_av_R_equivalents 0.0592 _diffrn_reflns_av_sigmaI/netI 0.1080 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 37 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.62 _diffrn_reflns_theta_max 28.01 _reflns_number_total 2169 _reflns_number_gt 1279 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _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. ; _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^)+(0.0076P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _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 0.048(15) _refine_ls_number_reflns 2169 _refine_ls_number_parameters 145 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0961 _refine_ls_R_factor_gt 0.0414 _refine_ls_wR_factor_ref 0.0531 _refine_ls_wR_factor_gt 0.0451 _refine_ls_goodness_of_fit_ref 0.816 _refine_ls_restrained_S_all 0.815 _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 Zn Zn 0.0000 0.0000 0.96205(7) 0.04415(18) Uani 1 2 d S . . O11 O 0.0409(2) -0.05142(11) 0.8347(3) 0.0512(8) Uani 1 1 d . . . O12 O 0.1611(2) -0.07800(8) 0.7056(3) 0.0645(7) Uani 1 1 d . . . O13 O 0.1599(2) 0.01188(10) 0.9351(3) 0.0475(9) Uani 1 1 d . . . C11 C 0.1295(4) -0.04920(14) 0.7858(3) 0.0456(11) Uani 1 1 d . . . C12 C 0.2011(3) -0.00885(14) 0.8226(3) 0.0455(10) Uani 1 1 d . . . H12 H 0.2697 -0.0218 0.8429 0.055 Uiso 1 1 calc R . . C13 C 0.2127(2) 0.02591(12) 0.7143(4) 0.0550(11) Uani 1 1 d . . . H13A H 0.2589 0.0507 0.7403 0.082 Uiso 1 1 calc R . . H13B H 0.1461 0.0390 0.6936 0.082 Uiso 1 1 calc R . . H13C H 0.2406 0.0103 0.6400 0.082 Uiso 1 1 calc R . . N1 N -0.0100(3) 0.04646(14) 1.1228(3) 0.0411(10) Uani 1 1 d . . . C1 C -0.0199(3) 0.09226(15) 1.1233(4) 0.0496(12) Uani 1 1 d . . . H1 H -0.0204 0.1078 1.0444 0.059 Uiso 1 1 calc R . . C2 C -0.0295(3) 0.11903(16) 1.2339(5) 0.0587(12) Uani 1 1 d . . . H2 H -0.0375 0.1515 1.2284 0.070 Uiso 1 1 calc R . . C3 C -0.0271(3) 0.09782(15) 1.3490(4) 0.0569(13) Uani 1 1 d . . . H3 H -0.0348 0.1154 1.4240 0.068 Uiso 1 1 calc R . . C4 C -0.0128(3) 0.04885(15) 1.3561(4) 0.0470(11) Uani 1 1 d . . . C5 C -0.0058(3) 0.02490(11) 1.2398(3) 0.0367(9) Uani 1 1 d . . . C6 C -0.0072(4) 0.02296(12) 1.4737(5) 0.0567(11) Uani 1 1 d . . . H6 H -0.0137 0.0388 1.5518 0.068 Uiso 1 1 calc R . . O1 O 0.0148(3) -0.15404(13) 0.7258(4) 0.0650(10) Uani 1 1 d . . . H13 H 0.187(3) 0.0341(11) 0.937(4) 0.033(14) Uiso 1 1 d . . . H1W H -0.001(4) -0.1595(17) 0.811(4) 0.11(2) Uiso 1 1 d . . . H2W H 0.043(4) -0.1330(16) 0.720(7) 0.09(2) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Zn 0.0523(4) 0.0415(4) 0.0387(3) 0.000 0.000 -0.0044(5) O11 0.057(2) 0.042(2) 0.054(2) -0.0142(17) 0.0055(17) -0.0048(18) O12 0.096(2) 0.0412(16) 0.0568(16) -0.0080(18) 0.013(2) 0.0110(16) O13 0.0557(18) 0.051(2) 0.036(2) -0.0027(17) -0.0026(13) -0.0098(17) C11 0.072(3) 0.031(2) 0.033(2) 0.004(2) -0.007(2) 0.011(2) C12 0.046(2) 0.048(3) 0.043(2) 0.007(2) 0.0017(18) 0.004(2) C13 0.060(3) 0.054(2) 0.051(2) 0.005(3) 0.011(3) -0.0022(18) N1 0.039(2) 0.038(2) 0.047(3) 0.0058(18) 0.0060(19) -0.008(2) C1 0.052(3) 0.047(3) 0.050(3) 0.005(2) 0.003(2) -0.007(2) C2 0.066(3) 0.042(3) 0.068(3) -0.010(3) 0.008(3) 0.002(2) C3 0.053(3) 0.058(3) 0.059(3) -0.020(3) 0.006(2) 0.004(3) C4 0.041(3) 0.058(3) 0.043(2) -0.007(2) 0.002(2) 0.000(3) C5 0.0278(19) 0.045(2) 0.037(2) -0.0022(18) 0.001(2) -0.005(2) C6 0.058(3) 0.081(3) 0.032(2) -0.008(3) -0.003(3) 0.001(4) O1 0.075(2) 0.046(2) 0.074(3) -0.008(2) 0.007(3) -0.0032(19) _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 Zn O11 2.038(3) . ? Zn O11 2.038(3) 2 ? Zn O13 2.105(3) 2 ? Zn O13 2.105(3) . ? Zn N1 2.131(4) 2 ? Zn N1 2.131(4) . ? O11 C11 1.250(5) . ? O12 C11 1.236(4) . ? O13 C12 1.411(4) . ? C11 C12 1.520(5) . ? C12 C13 1.503(5) . ? N1 C1 1.307(5) . ? N1 C5 1.361(4) . ? C1 C2 1.382(6) . ? C2 C3 1.337(6) . ? C3 C4 1.405(5) . ? C4 C5 1.388(5) . ? C4 C6 1.427(6) . ? C5 C5 1.422(6) 2 ? C6 C6 1.317(7) 2 ? 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 O11 Zn O11 99.21(17) . 2 ? O11 Zn O13 92.98(12) . 2 ? O11 Zn O13 77.04(13) 2 2 ? O11 Zn O13 77.04(13) . . ? O11 Zn O13 92.98(12) 2 . ? O13 Zn O13 164.72(16) 2 . ? O11 Zn N1 92.75(11) . 2 ? O11 Zn N1 165.16(15) 2 2 ? O13 Zn N1 93.67(12) 2 2 ? O13 Zn N1 98.28(12) . 2 ? O11 Zn N1 165.16(15) . . ? O11 Zn N1 92.75(11) 2 . ? O13 Zn N1 98.28(12) 2 . ? O13 Zn N1 93.67(12) . . ? N1 Zn N1 77.0(2) 2 . ? C11 O11 Zn 117.6(3) . . ? C12 O13 Zn 114.3(2) . . ? O12 C11 O11 122.8(4) . . ? O12 C11 C12 117.9(4) . . ? O11 C11 C12 119.3(4) . . ? O13 C12 C13 112.4(3) . . ? O13 C12 C11 107.1(3) . . ? C13 C12 C11 111.6(3) . . ? C1 N1 C5 116.6(4) . . ? C1 N1 Zn 128.7(3) . . ? C5 N1 Zn 114.7(3) . . ? N1 C1 C2 124.0(4) . . ? C3 C2 C1 119.4(4) . . ? C2 C3 C4 119.7(4) . . ? C5 C4 C3 116.6(4) . . ? C5 C4 C6 119.2(4) . . ? C3 C4 C6 124.2(4) . . ? N1 C5 C4 123.5(3) . . ? N1 C5 C5 116.8(2) . 2 ? C4 C5 C5 119.6(2) . 2 ? C6 C6 C4 121.2(2) 2 . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O13 H13 O1 0.72(3) 1.91(3) 2.612(5) 166(4) 4 O1 H1W O12 0.92(4) 1.91(4) 2.780(5) 156(4) 15_445 O1 H2W O12 0.70(4) 2.18(4) 2.874(5) 168(5) . O1 H2W O11 0.70(4) 2.61(5) 3.144(5) 135(7) . C1 H1 O12 0.93 2.48 3.181(5) 132 4 _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 28.01 _diffrn_measured_fraction_theta_full 0.987 _refine_diff_density_max 0.583 _refine_diff_density_min -0.210 _refine_diff_density_rms 0.051 #=========================================================================== data_znslphen _database_code_depnum_ccdc_archive 'CCDC 288315' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H18 N2 O6 Zn' _chemical_formula_weight 423.71 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' Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2 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' _cell_length_a 11.325(2) _cell_length_b 16.241(3) _cell_length_c 9.881(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1817.2(6) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.09 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.549 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 872 _exptl_absorpt_coefficient_mu 1.389 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9067 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11059 _diffrn_reflns_av_R_equivalents 0.0497 _diffrn_reflns_av_sigmaI/netI 0.1014 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.06 _diffrn_reflns_theta_max 27.97 _reflns_number_total 4180 _reflns_number_gt 2470 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _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. ; _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^)+(0.0120P)^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 0.024(15) _refine_ls_number_reflns 4180 _refine_ls_number_parameters 256 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0861 _refine_ls_R_factor_gt 0.0375 _refine_ls_wR_factor_ref 0.0556 _refine_ls_wR_factor_gt 0.0491 _refine_ls_goodness_of_fit_ref 0.809 _refine_ls_restrained_S_all 0.809 _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 Zn1 Zn 0.0000 0.0000 0.86212(4) 0.03514(15) Uani 1 2 d S . . O11 O 0.1517(2) 0.06550(16) 0.8303(2) 0.0423(7) Uani 1 1 d . . . O12 O 0.2413(2) 0.1625(2) 0.7081(3) 0.0553(13) Uani 1 1 d . . . O13 O -0.0536(2) 0.09306(16) 0.7216(2) 0.0364(7) Uani 1 1 d D . . C11 C 0.1523(3) 0.1233(2) 0.7469(4) 0.0345(10) Uani 1 1 d . . . C12 C 0.0348(3) 0.1511(2) 0.6849(4) 0.0387(10) Uani 1 1 d . . . H12 H 0.0429 0.1507 0.5861 0.046 Uiso 1 1 calc R . . C13 C 0.0049(5) 0.2373(2) 0.7292(4) 0.0976(15) Uani 1 1 d . . . H13A H -0.0697 0.2531 0.6913 0.146 Uiso 1 1 calc R . . H13B H 0.0651 0.2745 0.6984 0.146 Uiso 1 1 calc R . . H13C H 0.0004 0.2393 0.8262 0.146 Uiso 1 1 calc R . . N1 N -0.0826(3) 0.0595(2) 1.0329(3) 0.0472(9) Uani 1 1 d . . . C14 C -0.1675(4) 0.1150(3) 1.0315(5) 0.0638(14) Uani 1 1 d . . . H14 H -0.1943 0.1345 0.9485 0.077 Uiso 1 1 calc R . . C15 C -0.2192(5) 0.1461(4) 1.1509(6) 0.092(2) Uani 1 1 d . . . H15 H -0.2788 0.1854 1.1467 0.110 Uiso 1 1 calc R . . C16 C -0.1803(6) 0.1173(4) 1.2722(6) 0.105(3) Uani 1 1 d . . . H16 H -0.2143 0.1368 1.3517 0.126 Uiso 1 1 calc R . . C17 C -0.0899(5) 0.0589(4) 1.2788(5) 0.0830(19) Uani 1 1 d . . . C18 C -0.0452(3) 0.0306(2) 1.1544(4) 0.0524(15) Uani 1 1 d . . . C19 C -0.0429(5) 0.0266(5) 1.4023(4) 0.124(5) Uani 1 1 d . . . H19 H -0.0745 0.0439 1.4844 0.149 Uiso 1 1 calc R . . H13 H -0.120(2) 0.117(2) 0.699(4) 0.064(16) Uiso 1 1 d D . . Zn2 Zn 0.5000 0.0000 0.55450(4) 0.03610(15) Uani 1 2 d S . . O21 O 0.6535(2) 0.06188(17) 0.5905(2) 0.0459(7) Uani 1 1 d . . . O22 O 0.7421(2) 0.1656(2) 0.6956(4) 0.0589(13) Uani 1 1 d . . . O23 O 0.4489(2) 0.09622(16) 0.6903(3) 0.0392(7) Uani 1 1 d D . . C21 C 0.6529(3) 0.1262(3) 0.6596(4) 0.0393(11) Uani 1 1 d . . . C22 C 0.5326(3) 0.1614(2) 0.7007(4) 0.0376(10) Uani 1 1 d . . . H22 H 0.5109 0.2046 0.6360 0.045 Uiso 1 1 calc R . . C23 C 0.5325(3) 0.1984(2) 0.8428(3) 0.0571(12) Uani 1 1 d . . . H23A H 0.4542 0.2166 0.8652 0.086 Uiso 1 1 calc R . . H23B H 0.5857 0.2445 0.8457 0.086 Uiso 1 1 calc R . . H23C H 0.5575 0.1576 0.9069 0.086 Uiso 1 1 calc R . . N2 N 0.4077(3) 0.0520(2) 0.3828(3) 0.0468(9) Uani 1 1 d . . . C24 C 0.3110(4) 0.0979(3) 0.3857(5) 0.0584(13) Uani 1 1 d . . . H24 H 0.2818 0.1155 0.4688 0.070 Uiso 1 1 calc R . . C25 C 0.2516(4) 0.1207(3) 0.2671(6) 0.080(2) Uani 1 1 d . . . H25 H 0.1835 0.1527 0.2721 0.096 Uiso 1 1 calc R . . C26 C 0.2937(6) 0.0961(4) 0.1450(6) 0.099(3) Uani 1 1 d . . . H26 H 0.2548 0.1113 0.0660 0.119 Uiso 1 1 calc R . . C27 C 0.3940(5) 0.0486(3) 0.1386(5) 0.0754(18) Uani 1 1 d . . . C28 C 0.4492(3) 0.0258(2) 0.2608(4) 0.0506(14) Uani 1 1 d . . . C29 C 0.4511(5) 0.0215(5) 0.0146(4) 0.118(4) Uani 1 1 d . . . H29 H 0.4169 0.0352 -0.0679 0.142 Uiso 1 1 calc R . . H23 H 0.378(2) 0.122(2) 0.688(4) 0.061(16) Uiso 1 1 d 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 Zn1 0.0293(3) 0.0462(4) 0.0299(3) 0.000 0.000 0.0014(5) O11 0.0285(15) 0.0520(18) 0.0465(16) 0.0085(15) -0.0081(13) -0.0036(14) O12 0.0218(19) 0.051(3) 0.093(4) 0.0109(19) 0.0064(18) -0.0048(13) O13 0.0201(14) 0.0459(18) 0.0431(16) 0.0005(14) -0.0027(12) -0.0010(14) C11 0.027(2) 0.034(3) 0.043(3) -0.012(2) -0.001(2) 0.0049(19) C12 0.021(2) 0.047(3) 0.047(2) 0.007(2) -0.0075(15) -0.0016(18) C13 0.040(2) 0.040(2) 0.212(5) -0.002(3) -0.008(5) 0.009(3) N1 0.040(2) 0.056(2) 0.046(2) -0.012(2) 0.0109(18) -0.0074(18) C14 0.054(3) 0.063(3) 0.074(3) -0.028(3) 0.021(3) -0.010(3) C15 0.071(4) 0.088(5) 0.117(5) -0.050(5) 0.048(4) -0.013(3) C16 0.116(6) 0.129(7) 0.069(4) -0.057(5) 0.059(5) -0.069(5) C17 0.098(4) 0.099(5) 0.052(3) -0.033(4) 0.031(3) -0.057(3) C18 0.064(3) 0.066(4) 0.0271(19) -0.015(2) 0.0114(18) -0.037(2) C19 0.176(10) 0.163(12) 0.035(2) -0.026(4) 0.021(3) -0.129(8) Zn2 0.0270(3) 0.0496(4) 0.0317(3) 0.000 0.000 -0.0050(5) O21 0.0279(15) 0.0521(19) 0.0579(18) -0.0206(16) 0.0065(14) -0.0023(14) O22 0.023(2) 0.049(3) 0.104(4) -0.017(2) -0.0026(19) -0.0033(14) O23 0.0174(14) 0.0478(18) 0.0525(17) -0.0081(15) -0.0016(12) 0.0021(14) C21 0.023(2) 0.047(3) 0.047(3) 0.008(2) 0.000(2) 0.002(2) C22 0.024(2) 0.041(2) 0.048(2) 0.005(2) -0.0052(16) 0.0028(18) C23 0.045(3) 0.050(3) 0.076(3) -0.022(2) 0.011(2) -0.006(2) N2 0.048(2) 0.053(2) 0.040(2) 0.009(2) -0.0071(18) -0.0136(18) C24 0.055(3) 0.055(3) 0.065(3) 0.017(3) -0.021(3) -0.017(3) C25 0.072(4) 0.067(4) 0.100(5) 0.043(4) -0.042(4) -0.027(3) C26 0.130(6) 0.086(5) 0.080(5) 0.051(4) -0.067(5) -0.064(5) C27 0.114(5) 0.068(4) 0.045(3) 0.021(3) -0.035(3) -0.053(3) C28 0.069(3) 0.047(4) 0.037(2) 0.010(2) -0.0091(19) -0.034(2) C29 0.227(11) 0.097(9) 0.031(2) 0.010(3) -0.029(3) -0.088(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 Zn1 O11 2.045(2) 2 ? Zn1 O11 2.045(2) . ? Zn1 O13 2.140(3) 2 ? Zn1 O13 2.140(3) . ? Zn1 N1 2.158(3) . ? Zn1 N1 2.158(3) 2 ? O11 C11 1.249(4) . ? O12 C11 1.252(4) . ? O13 C12 1.422(4) . ? C11 C12 1.533(5) . ? C12 C13 1.506(4) . ? N1 C14 1.317(5) . ? N1 C18 1.358(4) . ? C14 C15 1.411(6) . ? C15 C16 1.359(8) . ? C16 C17 1.397(8) . ? C17 C18 1.407(5) . ? C17 C19 1.431(6) . ? C18 C18 1.426(7) 2 ? C19 C19 1.299(13) 2 ? Zn2 O21 2.039(2) . ? Zn2 O21 2.039(2) 2_655 ? Zn2 O23 2.139(2) . ? Zn2 O23 2.139(2) 2_655 ? Zn2 N2 2.164(3) . ? Zn2 N2 2.164(3) 2_655 ? O21 C21 1.248(4) . ? O22 C21 1.247(4) . ? O23 C22 1.425(4) . ? C21 C22 1.532(5) . ? C22 C23 1.528(4) . ? N2 C24 1.326(5) . ? N2 C28 1.361(4) . ? C24 C25 1.401(5) . ? C25 C26 1.358(8) . ? C26 C27 1.375(7) . ? C27 C28 1.409(5) . ? C27 C29 1.454(6) . ? C28 C28 1.425(7) 2_655 ? C29 C29 1.308(11) 2_655 ? 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 O11 Zn1 O11 162.34(13) 2 . ? O11 Zn1 O13 76.77(10) 2 2 ? O11 Zn1 O13 91.70(10) . 2 ? O11 Zn1 O13 91.70(10) 2 . ? O11 Zn1 O13 76.77(10) . . ? O13 Zn1 O13 99.09(13) 2 . ? O11 Zn1 N1 89.36(11) 2 . ? O11 Zn1 N1 104.55(10) . . ? O13 Zn1 N1 161.19(11) 2 . ? O13 Zn1 N1 93.89(11) . . ? O11 Zn1 N1 104.55(10) 2 2 ? O11 Zn1 N1 89.36(11) . 2 ? O13 Zn1 N1 93.89(11) 2 2 ? O13 Zn1 N1 161.19(11) . 2 ? N1 Zn1 N1 77.15(18) . 2 ? C11 O11 Zn1 119.8(2) . . ? C12 O13 Zn1 115.70(19) . . ? O11 C11 O12 126.1(4) . . ? O11 C11 C12 118.7(3) . . ? O12 C11 C12 115.3(4) . . ? O13 C12 C13 112.6(3) . . ? O13 C12 C11 108.3(3) . . ? C13 C12 C11 110.7(3) . . ? C14 N1 C18 118.3(4) . . ? C14 N1 Zn1 127.9(3) . . ? C18 N1 Zn1 113.6(3) . . ? N1 C14 C15 122.6(5) . . ? C16 C15 C14 118.7(6) . . ? C15 C16 C17 120.8(6) . . ? C16 C17 C18 116.4(6) . . ? C16 C17 C19 124.2(6) . . ? C18 C17 C19 119.4(6) . . ? N1 C18 C17 123.2(4) . . ? N1 C18 C18 117.7(2) . 2 ? C17 C18 C18 119.1(3) . 2 ? C19 C19 C17 121.5(3) 2 . ? O21 Zn2 O21 159.93(14) . 2_655 ? O21 Zn2 O23 76.20(9) . . ? O21 Zn2 O23 91.15(10) 2_655 . ? O21 Zn2 O23 91.15(10) . 2_655 ? O21 Zn2 O23 76.20(9) 2_655 2_655 ? O23 Zn2 O23 102.33(14) . 2_655 ? O21 Zn2 N2 110.86(11) . . ? O21 Zn2 N2 85.25(11) 2_655 . ? O23 Zn2 N2 94.36(11) . . ? O23 Zn2 N2 155.12(11) 2_655 . ? O21 Zn2 N2 85.25(11) . 2_655 ? O21 Zn2 N2 110.86(11) 2_655 2_655 ? O23 Zn2 N2 155.12(11) . 2_655 ? O23 Zn2 N2 94.36(11) 2_655 2_655 ? N2 Zn2 N2 76.74(19) . 2_655 ? C21 O21 Zn2 120.2(2) . . ? C22 O23 Zn2 114.1(2) . . ? O22 C21 O21 125.5(4) . . ? O22 C21 C22 116.9(4) . . ? O21 C21 C22 117.5(3) . . ? O23 C22 C23 111.0(3) . . ? O23 C22 C21 107.2(3) . . ? C23 C22 C21 113.0(3) . . ? C24 N2 C28 118.6(4) . . ? C24 N2 Zn2 127.0(3) . . ? C28 N2 Zn2 114.0(3) . . ? N2 C24 C25 121.9(5) . . ? C26 C25 C24 119.8(6) . . ? C25 C26 C27 119.8(6) . . ? C26 C27 C28 118.3(5) . . ? C26 C27 C29 125.2(5) . . ? C28 C27 C29 116.5(6) . . ? N2 C28 C27 121.6(4) . . ? N2 C28 C28 117.5(2) . 2_655 ? C27 C28 C28 120.9(3) . 2_655 ? C29 C29 C27 122.5(3) 2_655 . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O13 H13 O22 0.88 1.75 2.610(4) 166 1_455 O23 H23 O12 0.90 1.70 2.592(3) 171 . C13 H13A O22 0.96 2.56 3.214(6) 125 1_455 C19 H19 O13 0.93 2.49 3.336(5) 152 1_556 C24 H24 O12 0.93 2.53 3.446(6) 170 . _diffrn_measured_fraction_theta_max 0.980 _diffrn_reflns_theta_full 27.97 _diffrn_measured_fraction_theta_full 0.980 _refine_diff_density_max 0.582 _refine_diff_density_min -0.293 _refine_diff_density_rms 0.052 #====================================================================== data_mnld _database_code_depnum_ccdc_archive 'CCDC 288316' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 H17 Cl Mn N2 O5' _chemical_formula_weight 395.70 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Mn Mn 0.3368 0.7283 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c 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 7.9432(7) _cell_length_b 9.6697(8) _cell_length_c 22.3743(19) _cell_angle_alpha 90.00 _cell_angle_beta 92.791(2) _cell_angle_gamma 90.00 _cell_volume 1716.5(3) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prism _exptl_crystal_colour orange _exptl_crystal_size_max 0.33 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.23 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.531 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 812 _exptl_absorpt_coefficient_mu 0.951 _exptl_absorpt_correction_type multiscan _exptl_absorpt_correction_T_min 0.8169 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10157 _diffrn_reflns_av_R_equivalents 0.0298 _diffrn_reflns_av_sigmaI/netI 0.0537 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 1.82 _diffrn_reflns_theta_max 28.06 _reflns_number_total 3977 _reflns_number_gt 2774 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _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. ; _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^)+(0.0366P)^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_number_reflns 3977 _refine_ls_number_parameters 238 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0631 _refine_ls_R_factor_gt 0.0353 _refine_ls_wR_factor_ref 0.0779 _refine_ls_wR_factor_gt 0.0724 _refine_ls_goodness_of_fit_ref 0.916 _refine_ls_restrained_S_all 0.916 _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 Mn Mn 0.35377(4) 0.12655(3) 0.189913(13) 0.02873(10) Uani 1 1 d . . . O1 O 0.6160(2) 0.1689(2) 0.18501(9) 0.0475(5) Uani 1 1 d . . . H1A H 0.654(3) 0.226(3) 0.1680(12) 0.064(10) Uiso 1 1 d . . . H2B H 0.367(3) -0.011(3) 0.2948(12) 0.057(9) Uiso 1 1 d . . . H1B H 0.680(4) 0.109(3) 0.1909(12) 0.067(10) Uiso 1 1 d . . . O2 O 0.4225(3) 0.0062(2) 0.26687(9) 0.0575(6) Uani 1 1 d . . . H2A H 0.510(4) -0.044(3) 0.2696(13) 0.076(10) Uiso 1 1 d . . . O11 O 0.31936(17) 0.32276(14) 0.23483(6) 0.0350(4) Uani 1 1 d . . . O13 O 0.09467(19) 0.13328(16) 0.21919(7) 0.0427(4) Uani 1 1 d . . . O12 O 0.16249(18) 0.45674(15) 0.29052(7) 0.0435(4) Uani 1 1 d . . . C11 C 0.1849(3) 0.3499(2) 0.26034(10) 0.0335(5) Uani 1 1 d . . . C12 C 0.0385(3) 0.2492(2) 0.25187(11) 0.0459(6) Uani 1 1 d . . . H12 H -0.0494 0.2953 0.2269 0.055 Uiso 1 1 calc R . . C13 C -0.0363(4) 0.2106(3) 0.30842(12) 0.0714(9) Uani 1 1 d . . . H13A H -0.1331 0.1531 0.3001 0.107 Uiso 1 1 calc R . . H13B H -0.0697 0.2927 0.3289 0.107 Uiso 1 1 calc R . . H13C H 0.0453 0.1609 0.3331 0.107 Uiso 1 1 calc R . . N1 N 0.3604(2) -0.05299(17) 0.12433(8) 0.0338(4) Uani 1 1 d . . . N2 N 0.2690(2) 0.21251(18) 0.10020(8) 0.0362(4) Uani 1 1 d . . . C101 C 0.4169(3) -0.1807(2) 0.13508(11) 0.0417(6) Uani 1 1 d . . . H101 H 0.4534 -0.2036 0.1740 0.050 Uiso 1 1 calc R . . C102 C 0.4241(3) -0.2816(3) 0.09099(12) 0.0530(7) Uani 1 1 d . . . H102 H 0.4670 -0.3689 0.1002 0.064 Uiso 1 1 calc R . . C103 C 0.3674(3) -0.2507(3) 0.03404(12) 0.0552(7) Uani 1 1 d . . . H103 H 0.3692 -0.3176 0.0042 0.066 Uiso 1 1 calc R . . C104 C 0.3064(3) -0.1178(2) 0.02069(10) 0.0452(6) Uani 1 1 d . . . C105 C 0.3091(3) -0.0206(2) 0.06730(9) 0.0334(5) Uani 1 1 d . . . C106 C 0.2586(3) 0.1196(2) 0.05441(9) 0.0342(5) Uani 1 1 d . . . C107 C 0.2059(3) 0.1575(3) -0.00429(10) 0.0452(6) Uani 1 1 d . . . C108 C 0.1645(3) 0.2975(3) -0.01429(11) 0.0570(7) Uani 1 1 d . . . H108 H 0.1301 0.3271 -0.0525 0.068 Uiso 1 1 calc R . . C109 C 0.1746(3) 0.3890(3) 0.03128(12) 0.0597(7) Uani 1 1 d . . . H109 H 0.1479 0.4816 0.0248 0.072 Uiso 1 1 calc R . . C110 C 0.2256(3) 0.3422(2) 0.08806(11) 0.0515(7) Uani 1 1 d . . . H110 H 0.2295 0.4056 0.1193 0.062 Uiso 1 1 calc R . . C111 C 0.2463(4) -0.0763(3) -0.03826(11) 0.0629(8) Uani 1 1 d . . . H111 H 0.2402 -0.1413 -0.0689 0.075 Uiso 1 1 calc R . . C112 C 0.1992(4) 0.0540(3) -0.04976(11) 0.0626(8) Uani 1 1 d . . . H112 H 0.1611 0.0779 -0.0884 0.075 Uiso 1 1 calc R . . Cl Cl 0.75112(9) 0.42000(6) 0.11953(3) 0.05517(19) Uani 1 1 d . . . H13 H 0.019(3) 0.075(2) 0.2174(10) 0.046(7) 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 Mn 0.03204(17) 0.02451(17) 0.02964(18) -0.00100(14) 0.00154(13) 0.00093(14) O1 0.0350(10) 0.0351(11) 0.0728(13) 0.0150(10) 0.0058(9) 0.0008(9) O2 0.0618(13) 0.0634(13) 0.0491(12) 0.0289(10) 0.0227(10) 0.0299(10) O11 0.0293(8) 0.0293(8) 0.0468(9) -0.0095(7) 0.0053(7) -0.0035(6) O13 0.0347(9) 0.0316(9) 0.0627(11) -0.0165(8) 0.0129(8) -0.0103(7) O12 0.0380(9) 0.0273(8) 0.0652(11) -0.0166(8) 0.0035(8) 0.0033(7) C11 0.0304(12) 0.0273(12) 0.0425(13) -0.0003(10) -0.0012(10) 0.0019(9) C12 0.0379(13) 0.0380(14) 0.0625(16) -0.0116(12) 0.0099(12) -0.0041(11) C13 0.073(2) 0.076(2) 0.0686(19) -0.0221(17) 0.0312(16) -0.0279(16) N1 0.0365(10) 0.0282(10) 0.0366(11) 0.0005(8) 0.0010(8) 0.0006(8) N2 0.0439(11) 0.0297(10) 0.0349(10) 0.0026(8) 0.0000(8) 0.0028(8) C101 0.0439(14) 0.0326(13) 0.0482(14) -0.0008(11) -0.0018(11) 0.0002(11) C102 0.0597(17) 0.0311(14) 0.0686(19) -0.0062(13) 0.0073(15) 0.0057(12) C103 0.0718(19) 0.0408(15) 0.0539(17) -0.0187(13) 0.0120(14) -0.0027(13) C104 0.0531(15) 0.0435(14) 0.0395(13) -0.0104(12) 0.0073(11) -0.0046(12) C105 0.0332(12) 0.0353(13) 0.0321(12) -0.0043(10) 0.0058(10) -0.0026(9) C106 0.0350(12) 0.0385(12) 0.0295(11) 0.0012(10) 0.0043(9) -0.0022(10) C107 0.0494(15) 0.0524(16) 0.0336(13) 0.0062(11) 0.0004(11) -0.0031(12) C108 0.0698(19) 0.0625(18) 0.0379(14) 0.0187(14) -0.0062(13) 0.0058(15) C109 0.075(2) 0.0418(16) 0.0611(18) 0.0184(14) -0.0067(15) 0.0087(14) C110 0.0702(18) 0.0348(15) 0.0490(15) 0.0032(12) -0.0038(13) 0.0082(12) C111 0.086(2) 0.067(2) 0.0349(15) -0.0148(14) 0.0023(14) -0.0024(16) C112 0.087(2) 0.073(2) 0.0274(14) -0.0013(14) -0.0047(13) -0.0017(17) Cl 0.0846(5) 0.0380(3) 0.0448(4) 0.0001(3) 0.0228(3) -0.0048(3) _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 Mn O2 2.1275(18) . ? Mn O1 2.1305(17) . ? Mn O11 2.1706(13) . ? Mn O13 2.1909(15) . ? Mn N2 2.2455(17) . ? Mn N1 2.2754(17) . ? O11 C11 1.263(2) . ? O13 C12 1.422(2) . ? O12 C11 1.252(2) . ? C11 C12 1.521(3) . ? C12 C13 1.472(3) . ? N1 C101 1.332(3) . ? N1 C105 1.357(3) . ? N2 C110 1.325(3) . ? N2 C106 1.362(3) . ? C101 C102 1.390(3) . ? C102 C103 1.364(3) . ? C103 C104 1.400(3) . ? C104 C105 1.403(3) . ? C104 C111 1.438(3) . ? C105 C106 1.439(3) . ? C106 C107 1.408(3) . ? C107 C108 1.408(3) . ? C107 C112 1.426(3) . ? C108 C109 1.349(3) . ? C109 C110 1.390(3) . ? C111 C112 1.337(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O2 Mn O1 86.20(8) . . ? O2 Mn O11 97.86(7) . . ? O1 Mn O11 90.08(6) . . ? O2 Mn O13 88.98(7) . . ? O1 Mn O13 160.82(7) . . ? O11 Mn O13 72.20(5) . . ? O2 Mn N2 168.52(7) . . ? O1 Mn N2 97.71(8) . . ? O11 Mn N2 92.94(6) . . ? O13 Mn N2 90.63(7) . . ? O2 Mn N1 95.24(7) . . ? O1 Mn N1 93.44(7) . . ? O11 Mn N1 166.63(6) . . ? O13 Mn N1 105.49(6) . . ? N2 Mn N1 73.82(6) . . ? C11 O11 Mn 121.26(13) . . ? C12 O13 Mn 120.00(12) . . ? O12 C11 O11 124.09(19) . . ? O12 C11 C12 117.89(18) . . ? O11 C11 C12 117.98(18) . . ? O13 C12 C13 113.1(2) . . ? O13 C12 C11 108.15(17) . . ? C13 C12 C11 113.1(2) . . ? C101 N1 C105 117.83(19) . . ? C101 N1 Mn 127.53(15) . . ? C105 N1 Mn 114.52(13) . . ? C110 N2 C106 117.7(2) . . ? C110 N2 Mn 126.67(16) . . ? C106 N2 Mn 115.64(13) . . ? N1 C101 C102 123.2(2) . . ? C103 C102 C101 119.1(2) . . ? C102 C103 C104 119.7(2) . . ? C103 C104 C105 117.6(2) . . ? C103 C104 C111 123.2(2) . . ? C105 C104 C111 119.2(2) . . ? N1 C105 C104 122.5(2) . . ? N1 C105 C106 118.28(18) . . ? C104 C105 C106 119.2(2) . . ? N2 C106 C107 122.3(2) . . ? N2 C106 C105 117.69(19) . . ? C107 C106 C105 120.0(2) . . ? C106 C107 C108 117.1(2) . . ? C106 C107 C112 118.8(2) . . ? C108 C107 C112 124.1(2) . . ? C109 C108 C107 120.3(2) . . ? C108 C109 C110 118.8(2) . . ? N2 C110 C109 123.8(2) . . ? C112 C111 C104 121.1(2) . . ? C111 C112 C107 121.6(2) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1 H1A Cl 0.74(3) 2.32(3) 3.058(2) 174(3) . O2 H2B Cl 0.80(3) 2.28(3) 3.066(2) 170(2) 2_645 O1 H1B O12 0.78(3) 1.96(3) 2.741(2) 177(3) 2_645 O2 H2A O11 0.85(3) 1.87(3) 2.712(2) 169(3) 2_645 O13 H13 O12 0.82(2) 1.84(2) 2.663(2) 174(2) 2_545 C101 H101 O11 0.93 2.67 3.502(3) 149 2_645 _diffrn_measured_fraction_theta_max 0.951 _diffrn_reflns_theta_full 28.06 _diffrn_measured_fraction_theta_full 0.951 _refine_diff_density_max 0.561 _refine_diff_density_min -0.331 _refine_diff_density_rms 0.050 #====================================================================== data_colphencl _database_code_depnum_ccdc_archive 'CCDC 288317' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 H17 Cl Co N2 O5' _chemical_formula_weight 399.69 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 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21/c 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 7.8296(7) _cell_length_b 9.5624(8) _cell_length_c 22.1549(18) _cell_angle_alpha 90.00 _cell_angle_beta 93.724(2) _cell_angle_gamma 90.00 _cell_volume 1655.2(2) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prism _exptl_crystal_colour orange _exptl_crystal_size_max .15 _exptl_crystal_size_mid .11 _exptl_crystal_size_min .06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.604 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 820 _exptl_absorpt_coefficient_mu 1.226 _exptl_absorpt_correction_type MULTI-SCAN _exptl_absorpt_correction_T_min 0.851 _exptl_absorpt_correction_T_max 0.929 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9565 _diffrn_reflns_av_R_equivalents 0.0630 _diffrn_reflns_av_sigmaI/netI 0.1389 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_theta_min 1.84 _diffrn_reflns_theta_max 28.01 _reflns_number_total 3825 _reflns_number_gt 1998 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _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. ; _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^)+(0.0179P)^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_number_reflns 3825 _refine_ls_number_parameters 236 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1240 _refine_ls_R_factor_gt 0.0469 _refine_ls_wR_factor_ref 0.0768 _refine_ls_wR_factor_gt 0.0643 _refine_ls_goodness_of_fit_ref 0.838 _refine_ls_restrained_S_all 0.838 _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 Co Co 0.34920(6) 0.12105(4) 0.18947(2) 0.02554(14) Uani 1 1 d . . . O1 O 0.6054(4) 0.1572(3) 0.18189(15) 0.0444(9) Uani 1 1 d . . . H1A H 0.644(6) 0.215(4) 0.164(2) 0.067 Uiso 1 1 d . . . H2B H 0.358(5) -0.015(4) 0.2931(16) 0.048(14) Uiso 1 1 d . . . H1B H 0.672(5) 0.100(4) 0.1864(17) 0.042(15) Uiso 1 1 d . . . O2 O 0.4231(4) 0.0059(3) 0.26540(14) 0.0468(8) Uani 1 1 d . . . H2A H 0.505(5) -0.044(4) 0.2671(19) 0.070 Uiso 1 1 d . . . O11 O 0.3256(3) 0.3081(2) 0.23673(10) 0.0300(6) Uani 1 1 d . . . O13 O 0.0976(4) 0.1184(3) 0.21698(12) 0.0382(7) Uani 1 1 d . . . O12 O 0.1663(3) 0.4403(2) 0.29314(11) 0.0380(7) Uani 1 1 d . . . C11 C 0.1895(5) 0.3335(3) 0.26157(16) 0.0300(9) Uani 1 1 d . . . C12 C 0.0396(5) 0.2328(4) 0.2517(2) 0.0507(12) Uani 1 1 d . . . H12 H -0.0470 0.2817 0.2256 0.061 Uiso 1 1 calc R . . C13 C -0.0418(6) 0.1956(4) 0.30558(19) 0.0730(15) Uani 1 1 d . . . H13A H -0.1423 0.1411 0.2950 0.110 Uiso 1 1 calc R . . H13B H -0.0736 0.2789 0.3262 0.110 Uiso 1 1 calc R . . H13C H 0.0359 0.1417 0.3316 0.110 Uiso 1 1 calc R . . N1 N 0.3559(4) -0.0527(3) 0.12812(13) 0.0279(7) Uani 1 1 d . . . N2 N 0.2658(4) 0.2146(3) 0.10593(12) 0.0307(8) Uani 1 1 d . . . C101 C 0.4126(5) -0.1813(4) 0.13792(17) 0.0361(10) Uani 1 1 d . . . H101 H 0.4484 -0.2061 0.1773 0.043 Uiso 1 1 calc R . . C102 C 0.4219(5) -0.2821(4) 0.09276(19) 0.0448(11) Uani 1 1 d . . . H102 H 0.4649 -0.3707 0.1019 0.054 Uiso 1 1 calc R . . C103 C 0.3664(5) -0.2483(4) 0.03444(19) 0.0472(11) Uani 1 1 d . . . H103 H 0.3700 -0.3142 0.0037 0.057 Uiso 1 1 calc R . . C104 C 0.3044(5) -0.1132(4) 0.02195(16) 0.0384(9) Uani 1 1 d . . . C105 C 0.3060(4) -0.0176(3) 0.07023(16) 0.0283(9) Uani 1 1 d . . . C106 C 0.2561(4) 0.1246(4) 0.05802(15) 0.0297(8) Uani 1 1 d . . . C107 C 0.2048(5) 0.1661(4) -0.00110(17) 0.0388(10) Uani 1 1 d . . . C108 C 0.1654(5) 0.3082(4) -0.01017(18) 0.0496(12) Uani 1 1 d . . . H108 H 0.1329 0.3412 -0.0487 0.060 Uiso 1 1 calc R . . C109 C 0.1750(5) 0.3972(4) 0.03781(19) 0.0535(12) Uani 1 1 d . . . H109 H 0.1495 0.4915 0.0322 0.064 Uiso 1 1 calc R . . C110 C 0.2234(5) 0.3466(4) 0.09528(18) 0.0430(11) Uani 1 1 d . . . H110 H 0.2260 0.4085 0.1277 0.052 Uiso 1 1 calc R . . C111 C 0.2462(6) -0.0684(5) -0.03727(18) 0.0583(13) Uani 1 1 d . . . H111 H 0.2407 -0.1327 -0.0688 0.070 Uiso 1 1 calc R . . C112 C 0.1993(6) 0.0649(5) -0.04845(18) 0.0557(13) Uani 1 1 d . . . H112 H 0.1627 0.0914 -0.0876 0.067 Uiso 1 1 calc R . . Cl Cl 0.74332(15) 0.41499(9) 0.11937(4) 0.0503(3) Uani 1 1 d . . . H13 H 0.028(5) 0.067(4) 0.2155(17) 0.042(14) 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 Co 0.0311(3) 0.0212(2) 0.0244(3) -0.0007(2) 0.0023(2) 0.0006(2) O1 0.036(2) 0.034(2) 0.064(2) 0.0138(15) 0.0107(16) 0.0043(15) O2 0.053(2) 0.0517(19) 0.0374(18) 0.0190(15) 0.0184(17) 0.0235(15) O11 0.0278(16) 0.0267(13) 0.0358(15) -0.0070(11) 0.0045(12) -0.0028(11) O13 0.0355(18) 0.0282(15) 0.0523(18) -0.0130(15) 0.0142(14) -0.0111(15) O12 0.0382(18) 0.0276(14) 0.0487(18) -0.0123(12) 0.0072(14) 0.0023(12) C11 0.034(3) 0.024(2) 0.031(2) -0.0025(17) 0.0009(19) 0.0026(17) C12 0.052(3) 0.038(3) 0.065(3) -0.023(2) 0.026(2) -0.013(2) C13 0.092(4) 0.070(3) 0.062(3) -0.030(3) 0.040(3) -0.034(3) N1 0.034(2) 0.0232(16) 0.0268(18) 0.0018(14) 0.0006(15) -0.0016(13) N2 0.039(2) 0.0236(17) 0.0292(18) -0.0001(14) 0.0028(15) 0.0035(14) C101 0.042(3) 0.032(2) 0.035(2) -0.0045(19) 0.001(2) 0.0006(19) C102 0.056(3) 0.026(2) 0.053(3) -0.010(2) 0.004(2) 0.0061(19) C103 0.058(3) 0.036(2) 0.048(3) -0.019(2) 0.009(2) -0.004(2) C104 0.049(3) 0.034(2) 0.032(2) -0.005(2) 0.0077(19) -0.003(2) C105 0.031(2) 0.027(2) 0.027(2) -0.0025(17) 0.0027(18) -0.0009(17) C106 0.033(2) 0.035(2) 0.022(2) 0.0014(19) 0.0061(16) -0.0020(19) C107 0.044(3) 0.046(3) 0.028(2) 0.0057(19) 0.0038(19) 0.0028(19) C108 0.063(3) 0.053(3) 0.032(2) 0.012(2) -0.006(2) 0.005(2) C109 0.072(3) 0.037(3) 0.051(3) 0.019(2) -0.006(2) 0.003(2) C110 0.058(3) 0.028(2) 0.043(3) 0.0017(19) 0.000(2) 0.0048(19) C111 0.091(4) 0.058(3) 0.027(3) -0.011(2) 0.006(2) -0.001(3) C112 0.078(4) 0.066(3) 0.022(2) -0.003(2) -0.002(2) 0.001(3) Cl 0.0800(9) 0.0344(6) 0.0386(6) -0.0005(5) 0.0200(6) -0.0055(5) _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 Co O1 2.053(3) . ? Co O2 2.062(3) . ? Co O11 2.087(2) . ? Co O13 2.100(3) . ? Co N2 2.120(3) . ? Co N1 2.150(3) . ? O11 C11 1.254(4) . ? O13 C12 1.428(4) . ? O12 C11 1.258(4) . ? C11 C12 1.522(5) . ? C12 C13 1.435(5) . ? N1 C101 1.320(4) . ? N1 C105 1.358(4) . ? N2 C110 1.323(4) . ? N2 C106 1.365(4) . ? C101 C102 1.395(5) . ? C102 C103 1.375(5) . ? C103 C104 1.402(5) . ? C104 C105 1.406(4) . ? C104 C111 1.426(5) . ? C105 C106 1.435(4) . ? C106 C107 1.402(4) . ? C107 C108 1.405(5) . ? C107 C112 1.426(5) . ? C108 C109 1.360(5) . ? C109 C110 1.391(5) . ? C111 C112 1.345(5) . ? 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 Co O2 86.14(13) . . ? O1 Co O11 90.90(11) . . ? O2 Co O11 94.46(11) . . ? O1 Co O13 164.99(12) . . ? O2 Co O13 88.60(12) . . ? O11 Co O13 75.49(10) . . ? O1 Co N2 96.01(12) . . ? O2 Co N2 172.67(12) . . ? O11 Co N2 92.52(10) . . ? O13 Co N2 90.98(11) . . ? O1 Co N1 90.81(12) . . ? O2 Co N1 94.93(12) . . ? O11 Co N1 170.54(10) . . ? O13 Co N1 103.66(11) . . ? N2 Co N1 78.05(11) . . ? C11 O11 Co 119.4(2) . . ? C12 O13 Co 118.9(2) . . ? O11 C11 O12 123.9(3) . . ? O11 C11 C12 118.9(3) . . ? O12 C11 C12 117.1(4) . . ? O13 C12 C13 115.6(3) . . ? O13 C12 C11 107.0(3) . . ? C13 C12 C11 114.7(4) . . ? C101 N1 C105 117.3(3) . . ? C101 N1 Co 129.6(2) . . ? C105 N1 Co 112.9(2) . . ? C110 N2 C106 117.6(3) . . ? C110 N2 Co 128.2(3) . . ? C106 N2 Co 114.3(2) . . ? N1 C101 C102 123.9(4) . . ? C103 C102 C101 118.9(4) . . ? C102 C103 C104 119.1(4) . . ? C103 C104 C105 117.6(3) . . ? C103 C104 C111 123.0(4) . . ? C105 C104 C111 119.4(3) . . ? N1 C105 C104 123.1(3) . . ? N1 C105 C106 118.0(3) . . ? C104 C105 C106 118.9(3) . . ? N2 C106 C107 123.0(3) . . ? N2 C106 C105 116.8(3) . . ? C107 C106 C105 120.2(3) . . ? C106 C107 C108 117.1(4) . . ? C106 C107 C112 119.2(3) . . ? C108 C107 C112 123.7(4) . . ? C109 C108 C107 119.5(4) . . ? C108 C109 C110 119.7(4) . . ? N2 C110 C109 123.0(4) . . ? C112 C111 C104 121.4(4) . . ? C111 C112 C107 120.8(4) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O13 H13 O12 0.74(3) 1.94(3) 2.675(3) 176(4) 2_545 O2 H2A O11 0.80(4) 1.95(4) 2.732(3) 169(4) 2_645 O1 H1B O12 0.76(3) 2.02(3) 2.770(4) 173(4) 2_645 O2 H2B Cl 0.85(4) 2.24(4) 3.066(3) 164(3) 2_645 O1 H1A Cl 0.75(4) 2.32(4) 3.059(3) 171(5) . C101 H101 O11 0.93 2.52 3.345(4) 148.3 2_645 _diffrn_measured_fraction_theta_max 0.955 _diffrn_reflns_theta_full 28.01 _diffrn_measured_fraction_theta_full 0.955 _refine_diff_density_max 0.577 _refine_diff_density_min -0.365 _refine_diff_density_rms 0.071 #================================================================= data_nilphencl _database_code_depnum_ccdc_archive 'CCDC 288318' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 H17 Cl N2 Ni O5' _chemical_formula_weight 399.47 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c 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 7.7833(7) _cell_length_b 9.5585(9) _cell_length_c 22.055(2) _cell_angle_alpha 90.00 _cell_angle_beta 94.027(2) _cell_angle_gamma 90.00 _cell_volume 1636.8(3) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description 'hexagonal p' _exptl_crystal_colour 'light blue' _exptl_crystal_size_max .18 _exptl_crystal_size_mid .18 _exptl_crystal_size_min .08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.621 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 824 _exptl_absorpt_coefficient_mu 1.377 _exptl_absorpt_correction_type MULTI-SCAN _exptl_absorpt_correction_T_min 0.8223 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9682 _diffrn_reflns_av_R_equivalents 0.0517 _diffrn_reflns_av_sigmaI/netI 0.0760 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 1.85 _diffrn_reflns_theta_max 28.03 _reflns_number_total 3784 _reflns_number_gt 2516 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _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. ; _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^)+(0.0615P)^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_number_reflns 3784 _refine_ls_number_parameters 236 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0881 _refine_ls_R_factor_gt 0.0507 _refine_ls_wR_factor_ref 0.1194 _refine_ls_wR_factor_gt 0.1085 _refine_ls_goodness_of_fit_ref 0.950 _refine_ls_restrained_S_all 0.951 _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 Ni Ni 0.34746(6) 0.12056(4) 0.18894(2) 0.02522(14) Uani 1 1 d . . . O1 O 0.6021(4) 0.1549(3) 0.18039(15) 0.0457(8) Uani 1 1 d . . . H1A H 0.644(6) 0.213(5) 0.163(2) 0.069 Uiso 1 1 d . . . H2B H 0.348(5) -0.021(5) 0.287(2) 0.080(19) Uiso 1 1 d D . . H1B H 0.675(6) 0.087(4) 0.189(2) 0.051(14) Uiso 1 1 d . . . O2 O 0.4281(4) 0.0117(3) 0.26651(13) 0.0442(8) Uani 1 1 d D . . H2A H 0.503(6) -0.047(5) 0.267(2) 0.066 Uiso 1 1 d . . . O11 O 0.3293(3) 0.3033(2) 0.23673(11) 0.0309(6) Uani 1 1 d . . . O13 O 0.0977(3) 0.1142(3) 0.21579(13) 0.0397(7) Uani 1 1 d . . . O12 O 0.1686(3) 0.4358(3) 0.29304(13) 0.0399(7) Uani 1 1 d . . . C11 C 0.1922(5) 0.3285(4) 0.26186(17) 0.0310(8) Uani 1 1 d . . . C12 C 0.0448(6) 0.2266(5) 0.2519(3) 0.0644(15) Uani 1 1 d . . . H12 H -0.0409 0.2768 0.2255 0.077 Uiso 1 1 calc R . . C13 C -0.0433(7) 0.1907(7) 0.3034(3) 0.093(2) Uani 1 1 d . . . H13A H -0.1444 0.1376 0.2909 0.139 Uiso 1 1 calc R . . H13B H -0.0763 0.2743 0.3237 0.139 Uiso 1 1 calc R . . H13C H 0.0307 0.1356 0.3306 0.139 Uiso 1 1 calc R . . N1 N 0.3516(4) -0.0505(3) 0.13040(13) 0.0304(7) Uani 1 1 d . . . N2 N 0.2675(4) 0.2167(3) 0.10773(13) 0.0322(7) Uani 1 1 d . . . C101 C 0.4065(5) -0.1804(4) 0.14073(19) 0.0381(9) Uani 1 1 d . . . H101 H 0.4402 -0.2058 0.1805 0.046 Uiso 1 1 calc R . . C102 C 0.4165(6) -0.2812(4) 0.0951(2) 0.0458(11) Uani 1 1 d . . . H102 H 0.4592 -0.3701 0.1044 0.055 Uiso 1 1 calc R . . C103 C 0.3621(6) -0.2466(4) 0.0363(2) 0.0482(11) Uani 1 1 d . . . H103 H 0.3655 -0.3126 0.0054 0.058 Uiso 1 1 calc R . . C104 C 0.3022(6) -0.1121(4) 0.02365(18) 0.0431(10) Uani 1 1 d . . . C105 C 0.3037(5) -0.0156(4) 0.07190(16) 0.0309(8) Uani 1 1 d . . . C106 C 0.2565(5) 0.1261(4) 0.05959(16) 0.0324(8) Uani 1 1 d . . . C107 C 0.2055(6) 0.1694(4) 0.00016(18) 0.0422(10) Uani 1 1 d . . . C108 C 0.1666(6) 0.3113(5) -0.00896(19) 0.0520(12) Uani 1 1 d . . . H108 H 0.1344 0.3443 -0.0478 0.062 Uiso 1 1 calc R . . C109 C 0.1760(6) 0.4008(4) 0.0393(2) 0.0532(12) Uani 1 1 d . . . H109 H 0.1494 0.4950 0.0338 0.064 Uiso 1 1 calc R . . C110 C 0.2264(6) 0.3486(4) 0.09716(19) 0.0455(11) Uani 1 1 d . . . H110 H 0.2310 0.4103 0.1298 0.055 Uiso 1 1 calc R . . C111 C 0.2437(6) -0.0655(5) -0.03657(19) 0.0551(12) Uani 1 1 d . . . H111 H 0.2369 -0.1295 -0.0684 0.066 Uiso 1 1 calc R . . C112 C 0.1991(7) 0.0675(5) -0.04764(19) 0.0581(13) Uani 1 1 d . . . H112 H 0.1633 0.0944 -0.0870 0.070 Uiso 1 1 calc R . . Cl Cl 0.74199(16) 0.41357(10) 0.11853(5) 0.0482(3) Uani 1 1 d . . . H13 H 0.013(5) 0.050(4) 0.2149(18) 0.046(13) 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 Ni 0.0321(3) 0.0244(2) 0.0196(2) -0.00052(19) 0.00469(17) -0.0005(2) O1 0.0383(17) 0.0378(18) 0.063(2) 0.0167(15) 0.0160(15) 0.0034(14) O2 0.057(2) 0.0467(18) 0.0304(16) 0.0136(13) 0.0155(15) 0.0181(15) O11 0.0318(14) 0.0306(14) 0.0308(14) -0.0054(11) 0.0050(11) -0.0015(11) O13 0.0368(15) 0.0319(14) 0.0525(18) -0.0146(13) 0.0192(13) -0.0082(13) O12 0.0438(16) 0.0286(14) 0.0484(17) -0.0130(12) 0.0100(14) 0.0027(12) C11 0.034(2) 0.0262(18) 0.033(2) -0.0012(16) 0.0023(17) 0.0001(16) C12 0.061(3) 0.049(3) 0.088(4) -0.026(3) 0.042(3) -0.019(2) C13 0.094(4) 0.108(5) 0.084(4) -0.053(4) 0.059(4) -0.050(4) N1 0.0388(18) 0.0275(16) 0.0249(16) -0.0003(13) 0.0022(14) 0.0016(14) N2 0.0414(19) 0.0293(17) 0.0262(16) 0.0017(13) 0.0044(14) 0.0033(14) C101 0.043(2) 0.034(2) 0.037(2) -0.0030(18) -0.0027(18) -0.0006(18) C102 0.056(3) 0.029(2) 0.052(3) -0.0090(19) 0.002(2) 0.0018(19) C103 0.063(3) 0.042(2) 0.041(3) -0.0151(19) 0.014(2) -0.001(2) C104 0.054(3) 0.047(2) 0.028(2) -0.0058(18) 0.0076(18) -0.001(2) C105 0.035(2) 0.036(2) 0.0229(19) -0.0028(15) 0.0068(16) -0.0007(17) C106 0.037(2) 0.038(2) 0.0224(18) 0.0024(16) 0.0036(15) -0.0010(17) C107 0.053(3) 0.047(2) 0.027(2) 0.0065(18) 0.0054(19) -0.001(2) C108 0.066(3) 0.059(3) 0.030(2) 0.017(2) -0.001(2) 0.005(2) C109 0.072(3) 0.039(3) 0.048(3) 0.016(2) 0.000(2) 0.008(2) C110 0.062(3) 0.035(2) 0.039(2) 0.0009(18) 0.001(2) 0.007(2) C111 0.080(3) 0.061(3) 0.024(2) -0.013(2) 0.005(2) 0.002(3) C112 0.083(4) 0.072(3) 0.019(2) 0.002(2) 0.002(2) 0.005(3) Cl 0.0791(8) 0.0334(5) 0.0349(6) -0.0009(4) 0.0238(5) -0.0075(5) _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 Ni O1 2.031(3) . ? Ni O11 2.050(2) . ? Ni O2 2.062(3) . ? Ni N2 2.070(3) . ? Ni O13 2.072(3) . ? Ni N1 2.085(3) . ? O11 C11 1.260(4) . ? O13 C12 1.416(5) . ? O12 C11 1.255(4) . ? C11 C12 1.509(6) . ? C12 C13 1.409(6) . ? N1 C101 1.328(5) . ? N1 C105 1.359(4) . ? N2 C110 1.317(5) . ? N2 C106 1.368(5) . ? C101 C102 1.399(5) . ? C102 C103 1.376(6) . ? C103 C104 1.390(6) . ? C104 C105 1.408(5) . ? C104 C111 1.444(6) . ? C105 C106 1.424(5) . ? C106 C107 1.405(5) . ? C107 C108 1.401(6) . ? C107 C112 1.434(6) . ? C108 C109 1.363(6) . ? C109 C110 1.401(6) . ? C111 C112 1.335(6) . ? 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 Ni O11 90.73(11) . . ? O1 Ni O2 85.21(13) . . ? O11 Ni O2 91.79(11) . . ? O1 Ni N2 94.81(13) . . ? O11 Ni N2 92.25(11) . . ? O2 Ni N2 175.96(12) . . ? O1 Ni O13 166.51(12) . . ? O11 Ni O13 77.19(10) . . ? O2 Ni O13 89.14(12) . . ? N2 Ni O13 91.68(12) . . ? O1 Ni N1 90.68(13) . . ? O11 Ni N1 172.38(11) . . ? O2 Ni N1 95.80(12) . . ? N2 Ni N1 80.17(11) . . ? O13 Ni N1 102.09(11) . . ? C11 O11 Ni 118.7(2) . . ? C12 O13 Ni 117.0(2) . . ? O12 C11 O11 123.9(3) . . ? O12 C11 C12 117.9(3) . . ? O11 C11 C12 118.1(3) . . ? C13 C12 O13 116.4(4) . . ? C13 C12 C11 116.6(4) . . ? O13 C12 C11 108.9(3) . . ? C101 N1 C105 117.1(3) . . ? C101 N1 Ni 130.2(3) . . ? C105 N1 Ni 112.3(2) . . ? C110 N2 C106 117.9(3) . . ? C110 N2 Ni 129.2(3) . . ? C106 N2 Ni 112.9(2) . . ? N1 C101 C102 123.7(4) . . ? C103 C102 C101 118.9(4) . . ? C102 C103 C104 119.2(4) . . ? C103 C104 C105 118.0(4) . . ? C103 C104 C111 123.4(4) . . ? C105 C104 C111 118.6(4) . . ? N1 C105 C104 122.9(3) . . ? N1 C105 C106 117.7(3) . . ? C104 C105 C106 119.4(3) . . ? N2 C106 C107 122.4(4) . . ? N2 C106 C105 116.9(3) . . ? C107 C106 C105 120.7(4) . . ? C108 C107 C106 117.6(4) . . ? C108 C107 C112 123.8(4) . . ? C106 C107 C112 118.6(4) . . ? C109 C108 C107 119.7(4) . . ? C108 C109 C110 119.0(4) . . ? N2 C110 C109 123.4(4) . . ? C112 C111 C104 121.6(4) . . ? C111 C112 C107 121.1(4) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1 H1A Cl 0.76(5) 2.31(5) 3.061(3) 171(5) . O2 H2B Cl 0.852(19) 2.34(3) 3.088(3) 147(4) 2_645 O1 H1B O12 0.87(4) 1.92(5) 2.788(4) 179(4) 2_645 O2 H2A O11 0.81(5) 1.94(5) 2.749(4) 175(5) 2_645 O13 H13 O12 0.90(4) 1.79(4) 2.681(4) 173(4) 2_545 C101 H101 O11 0.93 2.47 3.283(5) 146.1 2_645 _diffrn_measured_fraction_theta_max 0.954 _diffrn_reflns_theta_full 28.03 _diffrn_measured_fraction_theta_full 0.954 _refine_diff_density_max 0.595 _refine_diff_density_min -0.904 _refine_diff_density_rms 0.098 #==================================================================== data_nilphenbr _database_code_depnum_ccdc_archive 'CCDC 288319' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 H17 Br N2 Ni O5' _chemical_formula_weight 443.93 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' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c 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 7.7340(8) _cell_length_b 9.6848(9) _cell_length_c 22.313(2) _cell_angle_alpha 90.00 _cell_angle_beta 94.977(2) _cell_angle_gamma 90.00 _cell_volume 1665.0(3) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prism _exptl_crystal_colour blue _exptl_crystal_size_max .08 _exptl_crystal_size_mid .03 _exptl_crystal_size_min .03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.771 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 896 _exptl_absorpt_coefficient_mu 3.593 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.879 _exptl_absorpt_correction_T_max 0.898 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8781 _diffrn_reflns_av_R_equivalents 0.0917 _diffrn_reflns_av_sigmaI/netI 0.2717 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.83 _diffrn_reflns_theta_max 27.93 _reflns_number_total 3634 _reflns_number_gt 1395 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _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. ; _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^)+(0.0068P)^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_number_reflns 3634 _refine_ls_number_parameters 236 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.1884 _refine_ls_R_factor_gt 0.0515 _refine_ls_wR_factor_ref 0.0756 _refine_ls_wR_factor_gt 0.0565 _refine_ls_goodness_of_fit_ref 0.736 _refine_ls_restrained_S_all 0.736 _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 Ni Ni 0.34589(11) 0.12052(8) 0.18932(4) 0.0269(2) Uani 1 1 d . . . O1 O 0.6020(6) 0.1499(4) 0.1809(3) 0.0452(15) Uani 1 1 d D . . H1A H 0.639(8) 0.233(4) 0.167(3) 0.068 Uiso 1 1 d D . . H2B H 0.373(8) 0.012(6) 0.297(3) 0.04(2) Uiso 1 1 d . . . H1B H 0.688(6) 0.091(5) 0.188(3) 0.09(3) Uiso 1 1 d D . . O2 O 0.4282(7) 0.0109(5) 0.2648(3) 0.0442(15) Uani 1 1 d D . . H2A H 0.514(5) -0.049(5) 0.263(3) 0.066 Uiso 1 1 d D . . O11 O 0.3308(5) 0.3001(4) 0.2360(2) 0.0299(12) Uani 1 1 d . . . O13 O 0.0962(5) 0.1147(5) 0.2160(2) 0.0389(13) Uani 1 1 d . . . O12 O 0.1721(5) 0.4342(4) 0.2899(2) 0.0409(14) Uani 1 1 d . . . C11 C 0.1949(9) 0.3296(6) 0.2597(3) 0.0264(18) Uani 1 1 d . . . C12 C 0.0455(10) 0.2278(7) 0.2503(4) 0.055(2) Uani 1 1 d . . . H12 H -0.0422 0.2760 0.2237 0.066 Uiso 1 1 calc R . . C13 C -0.0416(11) 0.1938(8) 0.3025(4) 0.084(3) Uani 1 1 d . . . H13A H -0.1414 0.1379 0.2908 0.126 Uiso 1 1 calc R . . H13B H -0.0778 0.2771 0.3211 0.126 Uiso 1 1 calc R . . H13C H 0.0360 0.1436 0.3305 0.126 Uiso 1 1 calc R . . N1 N 0.3474(6) -0.0478(5) 0.1318(2) 0.0253(14) Uani 1 1 d . . . N2 N 0.2647(7) 0.2149(5) 0.1091(3) 0.0292(15) Uani 1 1 d . . . C101 C 0.3994(8) -0.1760(6) 0.1420(3) 0.035(2) Uani 1 1 d . . . H101 H 0.4300 -0.2020 0.1816 0.042 Uiso 1 1 calc R . . C102 C 0.4114(9) -0.2742(7) 0.0974(4) 0.046(2) Uani 1 1 d . . . H102 H 0.4546 -0.3618 0.1071 0.055 Uiso 1 1 calc R . . C103 C 0.3593(9) -0.2415(7) 0.0394(4) 0.049(2) Uani 1 1 d . . . H103 H 0.3621 -0.3074 0.0091 0.059 Uiso 1 1 calc R . . C104 C 0.3018(9) -0.1082(7) 0.0259(3) 0.0399(19) Uani 1 1 d . . . C105 C 0.3000(8) -0.0116(6) 0.0738(3) 0.0329(18) Uani 1 1 d . . . C106 C 0.2565(8) 0.1267(7) 0.0618(3) 0.0298(17) Uani 1 1 d . . . C107 C 0.2076(9) 0.1720(7) 0.0026(3) 0.0353(19) Uani 1 1 d . . . C108 C 0.1695(9) 0.3089(8) -0.0070(4) 0.047(2) Uani 1 1 d . . . H108 H 0.1387 0.3412 -0.0458 0.056 Uiso 1 1 calc R . . C109 C 0.1772(9) 0.3969(7) 0.0406(3) 0.046(2) Uani 1 1 d . . . H109 H 0.1494 0.4898 0.0353 0.055 Uiso 1 1 calc R . . C110 C 0.2279(8) 0.3442(6) 0.0978(3) 0.043(2) Uani 1 1 d . . . H110 H 0.2359 0.4056 0.1300 0.052 Uiso 1 1 calc R . . C111 C 0.2471(9) -0.0639(8) -0.0327(4) 0.059(2) Uani 1 1 d . . . H111 H 0.2424 -0.1276 -0.0640 0.070 Uiso 1 1 calc R . . C112 C 0.2009(9) 0.0688(8) -0.0451(4) 0.061(2) Uani 1 1 d . . . H112 H 0.1647 0.0942 -0.0844 0.073 Uiso 1 1 calc R . . Br Br 0.74367(11) 0.41430(7) 0.11489(4) 0.0503(3) Uani 1 1 d . . . H13 H 0.025(7) 0.045(5) 0.219(3) 0.03(2) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Ni 0.0302(5) 0.0252(5) 0.0256(6) 0.0010(5) 0.0033(4) -0.0008(4) O1 0.035(3) 0.033(3) 0.068(4) 0.019(3) 0.008(3) 0.010(3) O2 0.054(4) 0.046(3) 0.034(4) 0.011(3) 0.015(3) 0.027(3) O11 0.026(3) 0.032(3) 0.032(3) -0.002(2) 0.007(3) -0.005(2) O13 0.030(3) 0.033(3) 0.056(4) -0.012(3) 0.018(3) -0.011(3) O12 0.040(3) 0.025(3) 0.057(4) -0.015(2) 0.006(3) 0.002(2) C11 0.031(5) 0.020(4) 0.027(5) 0.002(3) 0.000(4) -0.002(3) C12 0.075(6) 0.037(4) 0.060(7) -0.029(5) 0.038(5) -0.006(4) C13 0.106(8) 0.079(6) 0.075(8) -0.036(6) 0.050(7) -0.035(6) N1 0.026(4) 0.019(3) 0.030(4) 0.002(3) -0.004(3) -0.002(2) N2 0.031(4) 0.025(3) 0.031(4) 0.002(3) -0.001(3) 0.006(3) C101 0.033(5) 0.032(4) 0.039(5) -0.001(4) 0.001(4) -0.003(3) C102 0.062(6) 0.021(4) 0.053(6) -0.011(4) -0.002(5) 0.004(4) C103 0.064(6) 0.038(5) 0.044(6) -0.007(5) 0.008(5) -0.001(4) C104 0.048(5) 0.038(5) 0.034(5) -0.001(5) 0.005(4) 0.000(4) C105 0.037(5) 0.037(4) 0.025(5) -0.001(4) 0.003(4) 0.006(4) C106 0.029(4) 0.028(4) 0.032(5) -0.001(4) 0.005(4) -0.004(3) C107 0.035(5) 0.044(5) 0.028(5) 0.009(4) 0.003(4) -0.002(4) C108 0.040(5) 0.059(6) 0.039(6) 0.023(5) -0.007(4) 0.001(4) C109 0.072(6) 0.026(4) 0.037(5) 0.010(4) -0.001(5) 0.009(4) C110 0.042(5) 0.041(5) 0.046(6) 0.005(4) 0.000(4) 0.011(4) C111 0.084(7) 0.058(6) 0.034(6) -0.014(5) 0.003(5) 0.001(5) C112 0.082(7) 0.066(6) 0.033(5) 0.012(5) 0.000(5) -0.005(5) Br 0.0752(7) 0.0387(4) 0.0401(6) 0.0012(4) 0.0216(5) -0.0045(4) _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 Ni O1 2.026(5) . ? Ni O11 2.037(4) . ? Ni O2 2.045(5) . ? Ni N2 2.058(5) . ? Ni O13 2.070(4) . ? Ni N1 2.076(5) . ? O11 C11 1.249(7) . ? O13 C12 1.412(7) . ? O12 C11 1.238(7) . ? C11 C12 1.520(9) . ? C12 C13 1.433(10) . ? N1 C101 1.319(7) . ? N1 C105 1.360(7) . ? N2 C110 1.304(6) . ? N2 C106 1.355(7) . ? C101 C102 1.386(9) . ? C102 C103 1.360(9) . ? C103 C104 1.390(8) . ? C104 C111 1.407(9) . ? C104 C105 1.420(8) . ? C105 C106 1.402(8) . ? C106 C107 1.412(8) . ? C107 C108 1.371(8) . ? C107 C112 1.457(9) . ? C108 C109 1.359(9) . ? C109 C110 1.400(8) . ? C111 C112 1.356(9) . ? 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 Ni O11 91.56(19) . . ? O1 Ni O2 85.0(2) . . ? O11 Ni O2 92.8(2) . . ? O1 Ni N2 94.8(2) . . ? O11 Ni N2 92.23(19) . . ? O2 Ni N2 174.9(2) . . ? O1 Ni O13 167.0(2) . . ? O11 Ni O13 77.29(18) . . ? O2 Ni O13 88.9(2) . . ? N2 Ni O13 92.3(2) . . ? O1 Ni N1 89.7(2) . . ? O11 Ni N1 172.32(19) . . ? O2 Ni N1 94.8(2) . . ? N2 Ni N1 80.1(2) . . ? O13 Ni N1 102.23(19) . . ? C11 O11 Ni 119.9(4) . . ? C12 O13 Ni 116.4(4) . . ? O12 C11 O11 125.6(6) . . ? O12 C11 C12 117.6(7) . . ? O11 C11 C12 116.8(6) . . ? O13 C12 C13 115.8(6) . . ? O13 C12 C11 109.5(6) . . ? C13 C12 C11 116.3(7) . . ? C101 N1 C105 117.4(6) . . ? C101 N1 Ni 130.5(5) . . ? C105 N1 Ni 111.8(4) . . ? C110 N2 C106 117.4(6) . . ? C110 N2 Ni 129.7(5) . . ? C106 N2 Ni 112.8(4) . . ? N1 C101 C102 124.1(7) . . ? C103 C102 C101 119.4(7) . . ? C102 C103 C104 119.0(7) . . ? C103 C104 C111 123.3(7) . . ? C103 C104 C105 118.3(7) . . ? C111 C104 C105 118.5(6) . . ? N1 C105 C106 117.9(6) . . ? N1 C105 C104 121.7(6) . . ? C106 C105 C104 120.3(7) . . ? N2 C106 C105 117.4(6) . . ? N2 C106 C107 121.6(6) . . ? C105 C106 C107 121.0(7) . . ? C108 C107 C106 118.9(7) . . ? C108 C107 C112 123.7(7) . . ? C106 C107 C112 117.4(6) . . ? C109 C108 C107 119.3(7) . . ? C108 C109 C110 118.3(6) . . ? N2 C110 C109 124.5(7) . . ? C112 C111 C104 122.1(7) . . ? C111 C112 C107 120.6(7) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1 H1A Br 0.91(2) 2.30(3) 3.195(5) 168(6) . O2 H2B Br 0.87(6) 2.42(6) 3.235(6) 155(5) 2_645 O1 H1B O12 0.88(2) 1.90(3) 2.765(6) 166(7) 2_645 O2 H2A O11 0.886(19) 1.89(2) 2.766(6) 169(6) 2_645 O13 H13 O12 0.88(5) 1.86(5) 2.708(6) 162(5) 2_545 C101 H101 O11 0.93 2.49 3.290(8) 144.1 2_645 _diffrn_measured_fraction_theta_max 0.910 _diffrn_reflns_theta_full 27.93 _diffrn_measured_fraction_theta_full 0.910 _refine_diff_density_max 0.571 _refine_diff_density_min -0.489 _refine_diff_density_rms 0.094