# Electronic Supplementary Material (ESI) for Dalton Transactions. # This journal is © The Royal Society of Chemistry 2018 ####################################################################### # # This file contains crystal structure data downloaded from the # Cambridge Structural Database (CSD) hosted by the Cambridge # Crystallographic Data Centre (CCDC). # # Full information about CCDC data access policies and citation # guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 # # Audit and citation data items may have been added by the CCDC. # Please retain this information to preserve the provenance of # this file and to allow appropriate attribution of the data. # ####################################################################### data_mmn1_0m _database_code_depnum_ccdc_archive 'CCDC 1838773' _audit_update_record ; 2018-04-22 deposited with the CCDC. 2018-10-16 downloaded from the CCDC. ; _audit_creation_method SHELXL-2014/7 _shelx_SHELXL_version_number 2014/7 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C22 H18 Co N4 O4, Cl O4, 2(H2 O)' _chemical_formula_sum 'C22 H22 Cl Co N4 O10' _chemical_formula_weight 596.81 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' _space_group_crystal_system triclinic _space_group_IT_number 2 _space_group_name_H-M_alt 'P -1' _space_group_name_Hall '-P 1' _shelx_space_group_comment ; The symmetry employed for this shelxl refinement is uniquely defined by the following loop, which should always be used as a source of symmetry information in preference to the above space-group names. They are only intended as comments. ; loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.445(3) _cell_length_b 11.908(3) _cell_length_c 12.414(4) _cell_angle_alpha 99.74(3) _cell_angle_beta 103.51(3) _cell_angle_gamma 90.24(3) _cell_volume 1195.1(7) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 60965 _cell_measurement_theta_min 2.22 _cell_measurement_theta_max 30.10 _exptl_crystal_description block _exptl_crystal_colour orange _exptl_crystal_density_meas ? _exptl_crystal_density_method ? _exptl_crystal_density_diffrn 1.658 _exptl_crystal_F_000 612 _exptl_transmission_factor_min 0.600 _exptl_transmission_factor_max 0.876 _exptl_crystal_size_max 0.640 _exptl_crystal_size_mid 0.240 _exptl_crystal_size_min 0.150 _exptl_absorpt_coefficient_mu 0.897 _shelx_estimated_absorpt_T_min 0.598 _shelx_estimated_absorpt_T_max 0.877 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.600 _exptl_absorpt_correction_T_max 0.876 _exptl_absorpt_process_details 'Bruker, APEX2 v.2012.4-3' _exptl_absorpt_special_details ? _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_source ? _diffrn_measurement_device_type 'Bruker Quest D8 CMOS' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 60965 _diffrn_reflns_av_unetI/netI 0.0130 _diffrn_reflns_av_R_equivalents 0.0242 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.216 _diffrn_reflns_theta_max 30.119 _diffrn_reflns_theta_full 25.242 _diffrn_measured_fraction_theta_max 0.998 _diffrn_measured_fraction_theta_full 1.000 _diffrn_reflns_Laue_measured_fraction_max 0.998 _diffrn_reflns_Laue_measured_fraction_full 1.000 _diffrn_reflns_point_group_measured_fraction_max 0.998 _diffrn_reflns_point_group_measured_fraction_full 1.000 _reflns_number_total 7036 _reflns_number_gt 6562 _reflns_threshold_expression 'I > 2\s(I)' _reflns_Friedel_coverage 0.000 _reflns_Friedel_fraction_max . _reflns_Friedel_fraction_full . _reflns_special_details ; Reflections were merged by SHELXL according to the crystal class for the calculation of statistics and refinement. _reflns_Friedel_fraction is defined as the number of unique Friedel pairs measured divided by the number that would be possible theoretically, ignoring centric projections and systematic absences. ; _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _computing_structure_refinement 'SHELXL-2014/7 (Sheldrick, 2014)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ? _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0419P)^2^+0.8283P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary ? _atom_sites_solution_secondary ? _atom_sites_solution_hydrogens mixed _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef . _refine_ls_number_reflns 7036 _refine_ls_number_parameters 376 _refine_ls_number_restraints 21 _refine_ls_R_factor_all 0.0283 _refine_ls_R_factor_gt 0.0258 _refine_ls_wR_factor_ref 0.0755 _refine_ls_wR_factor_gt 0.0739 _refine_ls_goodness_of_fit_ref 1.016 _refine_ls_restrained_S_all 1.031 _refine_ls_shift/su_max 0.002 _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_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group Co1 Co 0.47320(2) 0.76504(2) 0.78374(2) 0.00649(5) Uani 1 1 d . . . . . O1W O 0.21727(14) 0.31022(10) 0.60435(10) 0.0257(2) Uani 1 1 d . . . . . H1W1 H 0.309(3) 0.296(2) 0.634(2) 0.043(6) Uiso 1 1 d . . . . . O2W O 0.34943(12) 0.53298(9) 0.36891(8) 0.01775(18) Uani 1 1 d . . . . . H1W2 H 0.416(3) 0.4898(19) 0.3594(18) 0.030(5) Uiso 1 1 d . . . . . H2W2 H 0.375(3) 0.591(2) 0.357(2) 0.043(7) Uiso 1 1 d . . . . . Cl1 Cl 0.35499(4) 0.75893(3) 0.21110(2) 0.01628(7) Uani 1 1 d D . . . . O8 O 0.44201(13) 0.75232(10) 0.32569(8) 0.0248(2) Uani 1 1 d D . . . . O5 O 0.18520(17) 0.7688(3) 0.20443(13) 0.0472(7) Uani 0.888(6) 1 d D . P A 1 O6 O 0.3842(4) 0.65922(17) 0.13736(14) 0.0390(5) Uani 0.888(6) 1 d D . P A 1 O7 O 0.4170(3) 0.85721(13) 0.17683(15) 0.0391(6) Uani 0.888(6) 1 d D . P A 1 O55 O 0.1975(14) 0.7047(13) 0.2062(10) 0.031(3) Uiso 0.112(6) 1 d D . P A 2 O66 O 0.4177(15) 0.6874(11) 0.1320(10) 0.017(3) Uiso 0.112(6) 1 d D . P A 2 O77 O 0.3563(18) 0.8698(9) 0.2075(13) 0.033(3) Uiso 0.112(6) 1 d D . P A 2 O1 O 0.50004(9) 0.90363(7) 0.88740(7) 0.00837(14) Uani 1 1 d . . . . . O2 O 0.72535(10) 0.99812(7) 1.02131(7) 0.01117(15) Uani 1 1 d . . . . . H2O H 0.6495 1.0252 1.0496 0.027(5) Uiso 1 1 calc R . . . . N1 N 0.67309(11) 0.81685(8) 0.75662(8) 0.00844(17) Uani 1 1 d . . . . . N2 N 0.60136(11) 0.70613(8) 0.90985(8) 0.00820(16) Uani 1 1 d . . . . . C1 C 0.72883(14) 0.79108(10) 0.66329(9) 0.0111(2) Uani 1 1 d . . . . . H1 H 0.6683 0.7381 0.6011 0.013 Uiso 1 1 calc R U . . . C2 C 0.87442(14) 0.84113(10) 0.65662(10) 0.0128(2) Uani 1 1 d . . . . . H2 H 0.9146 0.8222 0.5908 0.015 Uiso 1 1 calc R U . . . C3 C 0.96028(14) 0.91944(10) 0.74798(10) 0.0135(2) Uani 1 1 d . . . . . H3 H 1.0602 0.9543 0.7450 0.016 Uiso 1 1 calc R U . . . C4 C 0.89958(14) 0.94671(10) 0.84388(10) 0.0116(2) Uani 1 1 d . . . . . H4 H 0.9557 1.0010 0.9065 0.014 Uiso 1 1 calc R U . . . C5 C 0.75545(13) 0.89249(9) 0.84528(9) 0.00858(18) Uani 1 1 d . . . . . C6 C 0.66637(13) 0.90401(9) 0.94042(9) 0.00833(18) Uani 1 1 d . . . . . C7 C 0.68903(13) 0.79162(9) 0.98556(9) 0.00866(18) Uani 1 1 d . . . . . C8 C 0.78666(14) 0.77339(10) 1.08627(10) 0.0124(2) Uani 1 1 d . . . . . H8 H 0.8469 0.8348 1.1391 0.015 Uiso 1 1 calc R U . . . C9 C 0.79468(15) 0.66255(11) 1.10855(10) 0.0155(2) Uani 1 1 d . . . . . H9 H 0.8593 0.6473 1.1777 0.019 Uiso 1 1 calc R U . . . C10 C 0.70716(15) 0.57432(10) 1.02847(10) 0.0145(2) Uani 1 1 d . . . . . H10 H 0.7140 0.4980 1.0415 0.017 Uiso 1 1 calc R U . . . C11 C 0.60971(14) 0.59884(10) 0.92924(10) 0.0113(2) Uani 1 1 d . . . . . H11 H 0.5485 0.5390 0.8747 0.014 Uiso 1 1 calc R U . . . O3 O 0.44658(10) 0.62904(7) 0.67717(7) 0.00926(15) Uani 1 1 d . . . . . O4 O 0.22507(11) 0.53555(7) 0.54149(7) 0.01310(16) Uani 1 1 d . . . . . H4O H 0.2727 0.5344 0.4890 0.026(5) Uiso 1 1 calc R . . . . N3 N 0.27117(11) 0.71043(8) 0.80821(8) 0.00816(16) Uani 1 1 d . . . . . N4 N 0.35007(12) 0.82696(8) 0.65907(8) 0.00942(17) Uani 1 1 d . . . . . C12 C 0.21313(14) 0.73039(9) 0.90086(9) 0.01009(19) Uani 1 1 d . . . . . H12 H 0.2709 0.7823 0.9649 0.012 Uiso 1 1 calc R U . . . C13 C 0.06889(14) 0.67571(10) 0.90410(10) 0.0128(2) Uani 1 1 d . . . . . H13 H 0.0288 0.6895 0.9703 0.015 Uiso 1 1 calc R U . . . C14 C -0.01615(14) 0.60074(10) 0.80987(10) 0.0137(2) Uani 1 1 d . . . . . H14 H -0.1145 0.5626 0.8112 0.016 Uiso 1 1 calc R U . . . C15 C 0.04441(14) 0.58188(10) 0.71299(10) 0.0121(2) Uani 1 1 d . . . . . H15 H -0.0124 0.5320 0.6470 0.015 Uiso 1 1 calc R U . . . C16 C 0.18917(13) 0.63792(9) 0.71623(9) 0.00930(19) Uani 1 1 d . . . . . C17 C 0.28063(13) 0.63013(10) 0.62320(9) 0.00975(19) Uani 1 1 d . . . . . H17 H 0.228(3) 0.371(2) 0.592(2) 0.040(6) Uiso 1 1 d . . . . . C18 C 0.26072(13) 0.74416(10) 0.58087(9) 0.01030(19) Uani 1 1 d . . . . . C19 C 0.16783(15) 0.76686(11) 0.48016(10) 0.0146(2) Uani 1 1 d . . . . . H19 H 0.1043 0.7081 0.4257 0.018 Uiso 1 1 calc R U . . . C20 C 0.17046(17) 0.87877(12) 0.46114(11) 0.0192(2) Uani 1 1 d . . . . . H20 H 0.1093 0.8970 0.3923 0.023 Uiso 1 1 calc R U . . . C21 C 0.26232(17) 0.96364(12) 0.54258(11) 0.0190(2) Uani 1 1 d . . . . . H21 H 0.2635 1.0402 0.5303 0.023 Uiso 1 1 calc R U . . . C22 C 0.35254(15) 0.93520(10) 0.64231(10) 0.0138(2) Uani 1 1 d . . . . . H22 H 0.4160 0.9925 0.6987 0.017 Uiso 1 1 calc R U . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Co1 0.00604(7) 0.00644(7) 0.00663(7) -0.00010(5) 0.00167(5) 0.00032(5) O1W 0.0197(5) 0.0267(6) 0.0284(5) 0.0069(4) -0.0001(4) -0.0036(4) O2W 0.0184(4) 0.0167(4) 0.0205(5) 0.0024(4) 0.0101(4) 0.0063(4) Cl1 0.01846(14) 0.01530(13) 0.01357(13) 0.00103(10) 0.00187(10) 0.00198(10) O8 0.0231(5) 0.0354(6) 0.0136(4) 0.0041(4) 0.0003(4) 0.0021(4) O5 0.0163(6) 0.092(2) 0.0292(7) 0.0068(8) 0.0008(5) 0.0088(8) O6 0.0703(14) 0.0171(8) 0.0236(7) -0.0036(6) 0.0039(8) 0.0133(9) O7 0.0589(12) 0.0228(7) 0.0318(8) 0.0127(6) -0.0021(8) -0.0133(7) O1 0.0060(3) 0.0078(3) 0.0100(3) -0.0014(3) 0.0015(3) 0.0005(3) O2 0.0086(4) 0.0098(4) 0.0127(4) -0.0045(3) 0.0025(3) -0.0012(3) N1 0.0076(4) 0.0085(4) 0.0094(4) 0.0011(3) 0.0026(3) 0.0007(3) N2 0.0076(4) 0.0086(4) 0.0087(4) 0.0012(3) 0.0029(3) 0.0009(3) C1 0.0117(5) 0.0126(5) 0.0099(5) 0.0019(4) 0.0042(4) 0.0028(4) C2 0.0124(5) 0.0153(5) 0.0137(5) 0.0050(4) 0.0069(4) 0.0037(4) C3 0.0094(5) 0.0162(5) 0.0171(5) 0.0061(4) 0.0052(4) 0.0004(4) C4 0.0093(5) 0.0119(5) 0.0135(5) 0.0030(4) 0.0022(4) -0.0008(4) C5 0.0082(4) 0.0076(4) 0.0099(4) 0.0013(4) 0.0023(4) 0.0014(3) C6 0.0069(4) 0.0079(4) 0.0094(4) -0.0005(4) 0.0018(4) 0.0001(3) C7 0.0070(4) 0.0102(5) 0.0092(4) 0.0009(4) 0.0033(4) 0.0006(4) C8 0.0106(5) 0.0154(5) 0.0104(5) 0.0015(4) 0.0014(4) -0.0002(4) C9 0.0139(5) 0.0197(6) 0.0138(5) 0.0077(4) 0.0019(4) 0.0022(4) C10 0.0145(5) 0.0136(5) 0.0172(5) 0.0073(4) 0.0044(4) 0.0023(4) C11 0.0114(5) 0.0093(5) 0.0140(5) 0.0024(4) 0.0041(4) 0.0005(4) O3 0.0074(3) 0.0092(3) 0.0095(3) -0.0018(3) 0.0013(3) 0.0009(3) O4 0.0131(4) 0.0139(4) 0.0100(4) -0.0045(3) 0.0028(3) -0.0030(3) N3 0.0079(4) 0.0076(4) 0.0087(4) 0.0005(3) 0.0020(3) 0.0004(3) N4 0.0083(4) 0.0110(4) 0.0092(4) 0.0017(3) 0.0026(3) 0.0014(3) C12 0.0122(5) 0.0090(5) 0.0096(5) 0.0014(4) 0.0037(4) 0.0020(4) C13 0.0128(5) 0.0141(5) 0.0135(5) 0.0039(4) 0.0062(4) 0.0022(4) C14 0.0095(5) 0.0154(5) 0.0170(5) 0.0035(4) 0.0044(4) -0.0004(4) C15 0.0094(5) 0.0123(5) 0.0136(5) 0.0006(4) 0.0020(4) -0.0009(4) C16 0.0084(5) 0.0097(5) 0.0092(4) 0.0004(4) 0.0017(4) 0.0009(4) C17 0.0083(5) 0.0108(5) 0.0088(4) -0.0015(4) 0.0017(4) -0.0005(4) C18 0.0084(5) 0.0137(5) 0.0091(5) 0.0009(4) 0.0034(4) 0.0014(4) C19 0.0124(5) 0.0210(6) 0.0098(5) 0.0022(4) 0.0015(4) 0.0025(4) C20 0.0192(6) 0.0253(6) 0.0136(5) 0.0082(5) 0.0017(4) 0.0058(5) C21 0.0218(6) 0.0187(6) 0.0183(6) 0.0093(5) 0.0040(5) 0.0048(5) C22 0.0150(5) 0.0123(5) 0.0147(5) 0.0039(4) 0.0039(4) 0.0014(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 Co1 O3 1.8859(11) . ? Co1 O1 1.8902(11) . ? Co1 N4 1.9133(12) . ? Co1 N1 1.9159(11) . ? Co1 N2 1.9238(12) . ? Co1 N3 1.9302(12) . ? O1W H1W1 0.81(3) . ? O1W H17 0.77(3) . ? O2W H1W2 0.78(2) . ? O2W H2W2 0.77(3) . ? Cl1 O77 1.328(10) . ? Cl1 O66 1.390(11) . ? Cl1 O5 1.4233(15) . ? Cl1 O6 1.4313(15) . ? Cl1 O7 1.4465(16) . ? Cl1 O8 1.4559(12) . ? Cl1 O55 1.460(10) . ? O1 C6 1.4047(14) . ? O2 C6 1.3759(14) . ? O2 H2O 0.8400 . ? N1 C1 1.3393(14) . ? N1 C5 1.3446(15) . ? N2 C11 1.3387(15) . ? N2 C7 1.3464(15) . ? C1 C2 1.3900(17) . ? C1 H1 0.9500 . ? C2 C3 1.3907(18) . ? C2 H2 0.9500 . ? C3 C4 1.3933(17) . ? C3 H3 0.9500 . ? C4 C5 1.3805(16) . ? C4 H4 0.9500 . ? C5 C6 1.5300(16) . ? C6 C7 1.5322(16) . ? C7 C8 1.3790(16) . ? C8 C9 1.3924(17) . ? C8 H8 0.9500 . ? C9 C10 1.3911(19) . ? C9 H9 0.9500 . ? C10 C11 1.3892(17) . ? C10 H10 0.9500 . ? C11 H11 0.9500 . ? O3 C17 1.4062(14) . ? O4 C17 1.3799(14) . ? O4 H4O 0.8400 . ? N3 C12 1.3385(14) . ? N3 C16 1.3494(15) . ? N4 C22 1.3407(15) . ? N4 C18 1.3460(16) . ? C12 C13 1.3909(17) . ? C12 H12 0.9500 . ? C13 C14 1.3891(18) . ? C13 H13 0.9500 . ? C14 C15 1.3984(17) . ? C14 H14 0.9500 . ? C15 C16 1.3793(16) . ? C15 H15 0.9500 . ? C16 C17 1.5233(16) . ? C17 C18 1.5330(17) . ? C18 C19 1.3818(17) . ? C19 C20 1.3931(19) . ? C19 H19 0.9500 . ? C20 C21 1.388(2) . ? C20 H20 0.9500 . ? C21 C22 1.3897(18) . ? C21 H21 0.9500 . ? C22 H22 0.9500 . ? 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 O3 Co1 O1 178.44(3) . . ? O3 Co1 N4 83.33(5) . . ? O1 Co1 N4 95.36(5) . . ? O3 Co1 N1 95.90(5) . . ? O1 Co1 N1 83.26(5) . . ? N4 Co1 N1 90.78(5) . . ? O3 Co1 N2 97.65(5) . . ? O1 Co1 N2 83.64(5) . . ? N4 Co1 N2 178.45(4) . . ? N1 Co1 N2 87.92(5) . . ? O3 Co1 N3 82.91(5) . . ? O1 Co1 N3 97.93(5) . . ? N4 Co1 N3 88.82(5) . . ? N1 Co1 N3 178.78(4) . . ? N2 Co1 N3 92.49(5) . . ? H1W1 O1W H17 103(2) . . ? H1W2 O2W H2W2 109(2) . . ? O77 Cl1 O66 117.6(8) . . ? O5 Cl1 O6 110.85(13) . . ? O5 Cl1 O7 109.25(13) . . ? O6 Cl1 O7 107.93(12) . . ? O77 Cl1 O8 104.3(6) . . ? O66 Cl1 O8 111.8(6) . . ? O5 Cl1 O8 110.34(9) . . ? O6 Cl1 O8 108.90(9) . . ? O7 Cl1 O8 109.53(8) . . ? O77 Cl1 O55 116.4(8) . . ? O66 Cl1 O55 104.6(7) . . ? O8 Cl1 O55 101.0(5) . . ? C6 O1 Co1 101.32(7) . . ? C6 O2 H2O 109.5 . . ? C1 N1 C5 120.88(10) . . ? C1 N1 Co1 128.39(8) . . ? C5 N1 Co1 110.64(8) . . ? C11 N2 C7 120.47(10) . . ? C11 N2 Co1 129.43(8) . . ? C7 N2 Co1 110.09(8) . . ? N1 C1 C2 120.57(11) . . ? N1 C1 H1 119.7 . . ? C2 C1 H1 119.7 . . ? C1 C2 C3 118.88(11) . . ? C1 C2 H2 120.6 . . ? C3 C2 H2 120.6 . . ? C2 C3 C4 119.92(11) . . ? C2 C3 H3 120.0 . . ? C4 C3 H3 120.0 . . ? C5 C4 C3 118.07(11) . . ? C5 C4 H4 121.0 . . ? C3 C4 H4 121.0 . . ? N1 C5 C4 121.67(11) . . ? N1 C5 C6 109.85(9) . . ? C4 C5 C6 128.47(10) . . ? O2 C6 O1 115.35(9) . . ? O2 C6 C5 111.16(9) . . ? O1 C6 C5 105.31(9) . . ? O2 C6 C7 113.15(9) . . ? O1 C6 C7 105.49(9) . . ? C5 C6 C7 105.59(9) . . ? N2 C7 C8 121.99(11) . . ? N2 C7 C6 110.23(10) . . ? C8 C7 C6 127.75(10) . . ? C7 C8 C9 118.26(11) . . ? C7 C8 H8 120.9 . . ? C9 C8 H8 120.9 . . ? C10 C9 C8 119.33(11) . . ? C10 C9 H9 120.3 . . ? C8 C9 H9 120.3 . . ? C11 C10 C9 119.43(11) . . ? C11 C10 H10 120.3 . . ? C9 C10 H10 120.3 . . ? N2 C11 C10 120.49(11) . . ? N2 C11 H11 119.8 . . ? C10 C11 H11 119.8 . . ? C17 O3 Co1 101.35(7) . . ? C17 O4 H4O 109.5 . . ? C12 N3 C16 120.29(10) . . ? C12 N3 Co1 129.37(8) . . ? C16 N3 Co1 110.24(8) . . ? C22 N4 C18 121.23(10) . . ? C22 N4 Co1 127.92(9) . . ? C18 N4 Co1 110.75(8) . . ? N3 C12 C13 120.52(11) . . ? N3 C12 H12 119.7 . . ? C13 C12 H12 119.7 . . ? C14 C13 C12 119.57(11) . . ? C14 C13 H13 120.2 . . ? C12 C13 H13 120.2 . . ? C13 C14 C15 119.39(11) . . ? C13 C14 H14 120.3 . . ? C15 C14 H14 120.3 . . ? C16 C15 C14 117.90(11) . . ? C16 C15 H15 121.0 . . ? C14 C15 H15 121.0 . . ? N3 C16 C15 122.32(11) . . ? N3 C16 C17 109.88(10) . . ? C15 C16 C17 127.80(10) . . ? O4 C17 O3 113.87(10) . . ? O4 C17 C16 110.54(9) . . ? O3 C17 C16 105.59(9) . . ? O4 C17 C18 114.58(10) . . ? O3 C17 C18 105.33(9) . . ? C16 C17 C18 106.24(9) . . ? N4 C18 C19 121.59(11) . . ? N4 C18 C17 109.65(10) . . ? C19 C18 C17 128.77(11) . . ? C18 C19 C20 117.81(12) . . ? C18 C19 H19 121.1 . . ? C20 C19 H19 121.1 . . ? C21 C20 C19 120.14(12) . . ? C21 C20 H20 119.9 . . ? C19 C20 H20 119.9 . . ? C20 C21 C22 119.17(12) . . ? C20 C21 H21 120.4 . . ? C22 C21 H21 120.4 . . ? N4 C22 C21 120.05(12) . . ? N4 C22 H22 120.0 . . ? C21 C22 H22 120.0 . . ? 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 O1W H1W1 O8 0.81(3) 2.15(3) 2.942(2) 167(2) 2_666 O2W H1W2 O3 0.78(2) 1.90(2) 2.6706(16) 172(2) 2_666 O2W H2W2 Cl1 0.77(3) 2.89(3) 3.5923(15) 151(2) . O2W H2W2 O8 0.77(3) 2.12(3) 2.8938(18) 179(3) . O2 H2O O1 0.84 1.78 2.6181(14) 174.1 2_677 C2 H2 O1W 0.95 2.65 3.344(2) 130.3 2_666 C4 H4 O2 0.95 2.63 3.225(2) 120.9 2_777 C10 H10 O6 0.95 2.62 3.142(3) 115.3 2_666 C11 H11 O6 0.95 2.42 3.048(2) 123.5 2_666 O4 H4O O2W 0.84 1.76 2.5929(15) 173.3 . C12 H12 O7 0.95 2.63 3.529(2) 157.9 1_556 C12 H12 O66 0.95 2.59 3.110(14) 114.5 1_556 C12 H12 O2 0.95 2.59 3.2171(17) 123.8 2_677 C15 H15 O4 0.95 2.60 3.498(2) 158.7 2_566 O1W H17 O4 0.77(3) 2.15(3) 2.9229(17) 172(2) . C19 H19 O1W 0.95 2.66 3.252(2) 121.3 2_566 C22 H22 O7 0.95 2.37 3.314(2) 173.8 2_676 C22 H22 O77 0.95 2.45 3.356(13) 158.3 2_676 _refine_diff_density_max 0.477 _refine_diff_density_min -0.537 _refine_diff_density_rms 0.079 _shelx_res_file ; mmn1_0m.res created by SHELXL-2014/7 TITL MMN1_0m_a.res in P-1 REM Old TITL MMN1_0m in P-1 REM SHELXT solution in P-1 REM R1 0.288, Rweak 0.009, Alpha 0.042, Orientation as input REM Formula found by SHELXT: C26 N6 O5 Co CELL 0.71073 8.445 11.908 12.414 99.74 103.51 90.24 ZERR 2.000 0.003 0.003 0.004 0.03 0.03 0.03 LATT 1 SFAC C H N O CO Cl UNIT 44 44 8 20 2 2 TEMP -173.140 SIZE 0.15 0.24 0.64 L.S. 10 BOND $H HTAB 2 acta SADI Cl1 O8 Cl1 O5 Cl1 O6 Cl1 O7 Cl1 O55 Cl1 O66 Cl1 O77 FMAP 2 PLAN 20 EQIV $1 -x+1, -y+1, -z+1 HTAB O1W O8_$1 HTAB O2W O3_$1 HTAB O2W Cl1 HTAB O2W O8 EQIV $2 -x+1, -y+2, -z+2 HTAB O2 O1_$2 HTAB C2 O1W_$1 EQIV $3 -x+2, -y+2, -z+2 HTAB C4 O2_$3 HTAB C10 O6_$1 HTAB C11 O6_$1 HTAB O4 O2W EQIV $4 x, y, z+1 HTAB C12 O7_$4 HTAB C12 O66_$4 HTAB C12 O2_$2 EQIV $5 -x, -y+1, -z+1 HTAB C15 O4_$5 HTAB O1W O4 HTAB C19 O1W_$5 EQIV $6 -x+1, -y+2, -z+1 HTAB C22 O7_$6 HTAB C22 O77_$6 WGHT 0.041900 0.828300 FVAR 0.55744 0.88830 CO1 5 0.473200 0.765044 0.783741 11.00000 0.00604 0.00644 = 0.00663 -0.00010 0.00167 0.00032 O1W 4 0.217272 0.310224 0.604346 11.00000 0.01975 0.02671 = 0.02843 0.00686 -0.00008 -0.00364 H1W1 2 0.309068 0.295708 0.633928 11.00000 0.04312 O2W 4 0.349431 0.532983 0.368910 11.00000 0.01843 0.01675 = 0.02052 0.00237 0.01006 0.00631 H1W2 2 0.416155 0.489837 0.359433 11.00000 0.02998 H2W2 2 0.374658 0.591336 0.356891 11.00000 0.04290 CL1 6 0.354988 0.758930 0.211103 11.00000 0.01846 0.01530 = 0.01357 0.00103 0.00187 0.00198 O8 4 0.442008 0.752325 0.325693 11.00000 0.02309 0.03541 = 0.01363 0.00408 0.00027 0.00208 PART 1 O5 4 0.185199 0.768812 0.204433 21.00000 0.01630 0.09231 = 0.02924 0.00675 0.00076 0.00883 O6 4 0.384183 0.659221 0.137360 21.00000 0.07027 0.01707 = 0.02357 -0.00363 0.00386 0.01331 O7 4 0.417004 0.857211 0.176829 21.00000 0.05885 0.02280 = 0.03177 0.01272 -0.00215 -0.01334 PART 2 O55 4 0.197482 0.704739 0.206175 -21.00000 0.03119 O66 4 0.417694 0.687388 0.132049 -21.00000 0.01686 O77 4 0.356339 0.869752 0.207465 -21.00000 0.03314 PART 0 rem rem O1 4 0.500041 0.903628 0.887401 11.00000 0.00597 0.00781 = 0.01005 -0.00139 0.00147 0.00046 O2 4 0.725349 0.998117 1.021306 11.00000 0.00863 0.00983 = 0.01271 -0.00450 0.00255 -0.00118 AFIX 147 H2O 2 0.649522 1.025212 1.049564 11.00000 0.02749 AFIX 0 N1 3 0.673089 0.816854 0.756619 11.00000 0.00759 0.00845 = 0.00938 0.00105 0.00258 0.00071 N2 3 0.601360 0.706126 0.909851 11.00000 0.00761 0.00864 = 0.00870 0.00117 0.00288 0.00089 C1 1 0.728830 0.791076 0.663292 11.00000 0.01171 0.01261 = 0.00985 0.00190 0.00416 0.00278 AFIX 43 H1 2 0.668342 0.738131 0.601125 11.00000 -1.20000 AFIX 0 C2 1 0.874425 0.841127 0.656615 11.00000 0.01236 0.01532 = 0.01367 0.00501 0.00689 0.00370 AFIX 43 H2 2 0.914605 0.822156 0.590750 11.00000 -1.20000 AFIX 0 C3 1 0.960283 0.919442 0.747979 11.00000 0.00938 0.01619 = 0.01709 0.00611 0.00522 0.00040 AFIX 43 H3 2 1.060199 0.954305 0.745007 11.00000 -1.20000 AFIX 0 C4 1 0.899579 0.946709 0.843876 11.00000 0.00932 0.01194 = 0.01346 0.00302 0.00216 -0.00078 AFIX 43 H4 2 0.955741 1.001032 0.906480 11.00000 -1.20000 AFIX 0 C5 1 0.755447 0.892492 0.845280 11.00000 0.00820 0.00764 = 0.00992 0.00132 0.00231 0.00143 C6 1 0.666366 0.904012 0.940418 11.00000 0.00686 0.00793 = 0.00942 -0.00051 0.00183 0.00007 C7 1 0.689035 0.791621 0.985565 11.00000 0.00697 0.01020 = 0.00918 0.00085 0.00330 0.00062 C8 1 0.786660 0.773393 1.086275 11.00000 0.01055 0.01545 = 0.01035 0.00145 0.00139 -0.00021 AFIX 43 H8 2 0.846861 0.834848 1.139071 11.00000 -1.20000 AFIX 0 C9 1 0.794683 0.662551 1.108551 11.00000 0.01391 0.01972 = 0.01379 0.00775 0.00188 0.00224 AFIX 43 H9 2 0.859270 0.647333 1.177731 11.00000 -1.20000 AFIX 0 C10 1 0.707159 0.574321 1.028473 11.00000 0.01455 0.01365 = 0.01724 0.00726 0.00441 0.00227 AFIX 43 H10 2 0.713967 0.497955 1.041534 11.00000 -1.20000 AFIX 0 C11 1 0.609711 0.598837 0.929242 11.00000 0.01140 0.00928 = 0.01404 0.00244 0.00410 0.00052 AFIX 43 H11 2 0.548546 0.539020 0.874742 11.00000 -1.20000 AFIX 0 rem rem O3 4 0.446578 0.629039 0.677174 11.00000 0.00742 0.00924 = 0.00953 -0.00183 0.00131 0.00086 O4 4 0.225072 0.535549 0.541487 11.00000 0.01310 0.01387 = 0.00999 -0.00453 0.00285 -0.00300 AFIX 147 H4O 2 0.272671 0.534439 0.489012 11.00000 0.02617 AFIX 0 N3 3 0.271174 0.710430 0.808207 11.00000 0.00793 0.00756 = 0.00866 0.00050 0.00197 0.00045 N4 3 0.350067 0.826963 0.659070 11.00000 0.00830 0.01100 = 0.00923 0.00172 0.00260 0.00138 C12 1 0.213133 0.730395 0.900861 11.00000 0.01218 0.00902 = 0.00957 0.00144 0.00367 0.00199 AFIX 43 H12 2 0.270912 0.782321 0.964912 11.00000 -1.20000 AFIX 0 C13 1 0.068887 0.675710 0.904099 11.00000 0.01279 0.01407 = 0.01354 0.00390 0.00621 0.00215 AFIX 43 H13 2 0.028777 0.689540 0.970324 11.00000 -1.20000 AFIX 0 C14 1 -0.016147 0.600743 0.809873 11.00000 0.00953 0.01536 = 0.01696 0.00352 0.00435 -0.00042 AFIX 43 H14 2 -0.114529 0.562639 0.811240 11.00000 -1.20000 AFIX 0 C15 1 0.044411 0.581884 0.712987 11.00000 0.00944 0.01233 = 0.01365 0.00059 0.00196 -0.00094 AFIX 43 H15 2 -0.012365 0.532049 0.647014 11.00000 -1.20000 AFIX 0 C16 1 0.189172 0.637918 0.716233 11.00000 0.00842 0.00969 = 0.00917 0.00043 0.00171 0.00090 C17 1 0.280635 0.630127 0.623196 11.00000 0.00832 0.01076 = 0.00881 -0.00151 0.00166 -0.00046 H17 2 0.227625 0.371019 0.591840 11.00000 0.04026 C18 1 0.260719 0.744155 0.580869 11.00000 0.00840 0.01369 = 0.00911 0.00089 0.00345 0.00141 C19 1 0.167831 0.766858 0.480158 11.00000 0.01237 0.02098 = 0.00983 0.00219 0.00146 0.00251 AFIX 43 H19 2 0.104265 0.708083 0.425676 11.00000 -1.20000 AFIX 0 C20 1 0.170462 0.878768 0.461141 11.00000 0.01922 0.02533 = 0.01358 0.00818 0.00166 0.00580 AFIX 43 H20 2 0.109253 0.897033 0.392287 11.00000 -1.20000 AFIX 0 C21 1 0.262322 0.963640 0.542579 11.00000 0.02179 0.01867 = 0.01828 0.00927 0.00398 0.00484 AFIX 43 H21 2 0.263503 1.040215 0.530295 11.00000 -1.20000 AFIX 0 C22 1 0.352545 0.935202 0.642309 11.00000 0.01500 0.01229 = 0.01472 0.00390 0.00389 0.00141 AFIX 43 H22 2 0.416029 0.992503 0.698654 11.00000 -1.20000 AFIX 0 HKLF 4 REM MMN1_0m_a.res in P-1 REM R1 = 0.0258 for 6562 Fo > 4sig(Fo) and 0.0283 for all 7036 data REM 376 parameters refined using 21 restraints END WGHT 0.0387 0.7061 REM Instructions for potential hydrogen bonds HTAB O1W O8_$1 HTAB O2W O3_$1 HTAB O2W Cl1 HTAB O2W O8 HTAB O2 O1_$2 HTAB C2 O1W_$1 HTAB C4 O2_$3 HTAB C10 O6_$1 HTAB C11 O6_$1 HTAB O4 O2W HTAB C12 O7_$4 HTAB C12 O66_$4 HTAB C12 O2_$2 HTAB C15 O4_$5 HTAB O1W O4 HTAB C19 O1W_$5 HTAB C22 O7_$6 HTAB C22 O77_$6 REM Highest difference peak 0.477, deepest hole -0.537, 1-sigma level 0.079 Q1 1 0.1387 0.7033 0.9037 11.00000 0.05 0.48 Q2 1 0.2401 0.6588 0.2305 11.00000 0.05 0.48 Q3 1 0.8022 0.8180 0.6618 11.00000 0.05 0.43 Q4 1 0.0229 0.5885 0.7639 11.00000 0.05 0.43 Q5 1 0.9143 0.8843 0.6988 11.00000 0.05 0.41 Q6 1 0.0353 0.6426 0.8587 11.00000 0.05 0.40 Q7 1 0.7185 0.9009 0.8922 11.00000 0.05 0.39 Q8 1 0.9344 0.9296 0.7950 11.00000 0.05 0.39 Q9 1 0.8272 0.9154 0.8442 11.00000 0.05 0.38 Q10 1 0.4666 0.8190 0.3370 11.00000 0.05 0.38 Q11 1 0.3012 0.9509 0.5988 11.00000 0.05 0.37 Q12 1 0.1224 0.6099 0.7172 11.00000 0.05 0.36 Q13 1 0.2321 0.6270 0.6748 11.00000 0.05 0.35 Q14 1 0.6824 0.8452 0.9619 11.00000 0.05 0.34 Q15 1 0.2247 0.6766 0.7616 11.00000 0.05 0.33 Q16 1 0.2671 0.8405 0.1754 11.00000 0.05 0.33 Q17 1 0.6716 0.5818 0.9699 11.00000 0.05 0.32 Q18 1 0.7201 0.8576 0.7966 11.00000 0.05 0.32 Q19 1 0.2098 0.7591 0.5362 11.00000 0.05 0.32 Q20 1 0.2117 0.9224 0.5133 11.00000 0.05 0.32 ; _shelx_res_checksum 67061