# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_[Co(bpma)Cl2] _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common '[Co(bpma)Cl2]' _chemical_melting_point 'not determined' _chemical_formula_moiety 'C18 H18 Cl2 Co N4, C H4 O' _chemical_formula_sum 'C19 H22 Cl2 Co N4 O' _chemical_formula_weight 452.24 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' Co Co 0.3494 0.9721 '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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 21/n' _symmetry_space_group_name_hall '-P 2yn' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 8.3723(9) _cell_length_b 15.8181(16) _cell_length_c 15.0692(16) _cell_angle_alpha 90.00 _cell_angle_beta 104.561(7) _cell_angle_gamma 90.00 _cell_volume 1931.6(4) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 2891 _cell_measurement_theta_min 1.90 _cell_measurement_theta_max 26.42 _exptl_crystal_description block _exptl_crystal_colour red _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.555 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 932 _exptl_absorpt_coefficient_mu 1.182 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5645 _exptl_absorpt_correction_T_max 0.7454 _exptl_absorpt_process_details 'Sadabs (Sheldrick, 1996)' _exptl_special_details ; X-ray crystallographic data for I were collected from a single crystal sample, which was mounted on a loop fiber. Data were collected using a Bruker smart diffractometer equiped with an APEX II CCD Detector, a graphite monochromator. The crystal-to-detector distance was 5.0 cm, and the data collection was carried out in 512 x 512 pixel mode. ; _diffrn_ambient_temperature 100(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 'Bruker Smart ApexII' _diffrn_measurement_method '\w -scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 14727 _diffrn_reflns_av_R_equivalents 0.0689 _diffrn_reflns_av_sigmaI/netI 0.0693 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.90 _diffrn_reflns_theta_max 26.42 _reflns_number_total 3958 _reflns_number_gt 2891 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker AXS, 1)' _computing_cell_refinement 'SAINT V7.68A(Bruker AXS, )' _computing_data_reduction 'SAINT V7.68A(Bruker AXS, )' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1540P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3958 _refine_ls_number_parameters 246 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0984 _refine_ls_R_factor_gt 0.0573 _refine_ls_wR_factor_ref 0.2394 _refine_ls_wR_factor_gt 0.1587 _refine_ls_goodness_of_fit_ref 1.131 _refine_ls_restrained_S_all 1.131 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Co1 Co 0.42006(9) 0.60591(5) 0.22311(5) 0.0125(3) Uani 1 1 d . . . Cl2 Cl 0.61490(16) 0.68181(9) 0.15906(9) 0.0166(3) Uani 1 1 d . . . Cl1 Cl 0.58785(17) 0.63339(10) 0.37519(9) 0.0201(4) Uani 1 1 d . . . C10 C 0.1991(7) 0.6427(4) 0.0377(4) 0.0177(12) Uani 1 1 d . . . C13 C 0.0924(7) 0.5986(4) 0.2720(4) 0.0171(12) Uani 1 1 d . . . N2 N 0.2918(6) 0.5809(3) 0.0860(3) 0.0136(10) Uani 1 1 d . . . N4 N 0.2361(6) 0.5587(3) 0.2895(3) 0.0162(10) Uani 1 1 d . . . N3 N 0.2238(6) 0.7028(3) 0.1885(3) 0.0161(10) Uani 1 1 d . . . C5 C 0.4232(7) 0.4488(4) 0.1098(4) 0.0155(12) Uani 1 1 d . . . C14 C -0.0319(7) 0.5784(4) 0.3138(4) 0.0185(12) Uani 1 1 d . . . H14 H -0.1341 0.6078 0.2990 0.022 Uiso 1 1 calc R . . C16 C 0.1477(8) 0.4727(4) 0.3972(4) 0.0231(13) Uani 1 1 d . . . H16 H 0.1703 0.4285 0.4414 0.028 Uiso 1 1 calc R . . C7 C 0.2226(7) 0.4900(4) -0.0429(4) 0.0185(12) Uani 1 1 d . . . H7 H 0.2349 0.4371 -0.0703 0.022 Uiso 1 1 calc R . . N1 N 0.4880(6) 0.4790(3) 0.1953(3) 0.0162(10) Uani 1 1 d . . . C6 C 0.3069(7) 0.5062(4) 0.0478(4) 0.0143(11) Uani 1 1 d . . . C18 C 0.2717(8) 0.7789(4) 0.2470(4) 0.0213(13) Uani 1 1 d . . . H18A H 0.3764 0.8011 0.2390 0.032 Uiso 1 1 calc R . . H18B H 0.2844 0.7636 0.3114 0.032 Uiso 1 1 calc R . . H18C H 0.1858 0.8222 0.2292 0.032 Uiso 1 1 calc R . . C11 C 0.2077(7) 0.7243(4) 0.0896(4) 0.0175(12) Uani 1 1 d . . . H11A H 0.3040 0.7579 0.0833 0.021 Uiso 1 1 calc R . . H11B H 0.1066 0.7580 0.0652 0.021 Uiso 1 1 calc R . . C2 C 0.6539(8) 0.3548(4) 0.2303(4) 0.0232(13) Uani 1 1 d . . . H2 H 0.7356 0.3237 0.2730 0.028 Uiso 1 1 calc R . . C12 C 0.0649(7) 0.6662(4) 0.1990(4) 0.0176(12) Uani 1 1 d . . . H12A H 0.0037 0.6416 0.1398 0.021 Uiso 1 1 calc R . . H12B H -0.0037 0.7118 0.2151 0.021 Uiso 1 1 calc R . . C15 C -0.0028(7) 0.5144(4) 0.3773(4) 0.0226(13) Uani 1 1 d . . . H15 H -0.0853 0.4987 0.4075 0.027 Uiso 1 1 calc R . . C1 C 0.5991(7) 0.4336(4) 0.2538(4) 0.0198(12) Uani 1 1 d . . . H1 H 0.6435 0.4550 0.3139 0.024 Uiso 1 1 calc R . . C17 C 0.2646(7) 0.4968(4) 0.3514(4) 0.0173(12) Uani 1 1 d . . . H17 H 0.3678 0.4683 0.3645 0.021 Uiso 1 1 calc R . . C3 C 0.5856(8) 0.3233(4) 0.1428(4) 0.0259(14) Uani 1 1 d . . . H3 H 0.6197 0.2698 0.1255 0.031 Uiso 1 1 calc R . . C4 C 0.4684(8) 0.3696(4) 0.0811(4) 0.0212(13) Uani 1 1 d . . . H4 H 0.4199 0.3487 0.0212 0.025 Uiso 1 1 calc R . . C8 C 0.1207(7) 0.5519(4) -0.0926(4) 0.0209(13) Uani 1 1 d . . . H8 H 0.0603 0.5411 -0.1539 0.025 Uiso 1 1 calc R . . C9 C 0.1077(7) 0.6294(4) -0.0523(4) 0.0210(13) Uani 1 1 d . . . H9 H 0.0382 0.6725 -0.0851 0.025 Uiso 1 1 calc R . . O100 O 0.4130(6) 0.6196(3) 0.5382(3) 0.0307(11) Uani 1 1 d . . . H100 H 0.4532 0.6098 0.4935 0.046 Uiso 1 1 calc R . . C100 C 0.2796(8) 0.6776(5) 0.5113(5) 0.0325(16) Uani 1 1 d . . . H10A H 0.2165 0.6787 0.5580 0.049 Uiso 1 1 calc R . . H10B H 0.2075 0.6598 0.4525 0.049 Uiso 1 1 calc R . . H10C H 0.3230 0.7342 0.5050 0.049 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Co1 0.0119(4) 0.0133(5) 0.0129(4) -0.0003(3) 0.0040(3) 0.0010(3) Cl2 0.0163(7) 0.0182(7) 0.0163(6) -0.0009(5) 0.0060(5) -0.0037(5) Cl1 0.0163(7) 0.0299(9) 0.0139(6) -0.0019(6) 0.0036(5) -0.0015(6) C10 0.019(3) 0.019(3) 0.016(3) 0.001(2) 0.005(2) 0.001(2) C13 0.017(3) 0.020(3) 0.016(3) 0.000(2) 0.008(2) 0.001(2) N2 0.015(2) 0.012(2) 0.016(2) -0.0025(18) 0.0083(19) 0.0000(19) N4 0.016(2) 0.020(3) 0.014(2) -0.0015(19) 0.0055(19) 0.000(2) N3 0.015(2) 0.017(3) 0.017(2) 0.0029(19) 0.0050(19) 0.002(2) C5 0.016(3) 0.018(3) 0.015(3) -0.001(2) 0.009(2) -0.003(2) C14 0.016(3) 0.020(3) 0.021(3) -0.006(2) 0.008(2) -0.001(2) C16 0.025(3) 0.024(3) 0.022(3) -0.003(3) 0.010(3) 0.001(3) C7 0.017(3) 0.021(3) 0.020(3) -0.006(2) 0.009(2) -0.005(2) N1 0.013(2) 0.019(3) 0.018(2) -0.0014(19) 0.0069(19) -0.002(2) C6 0.014(3) 0.016(3) 0.015(3) 0.000(2) 0.008(2) -0.003(2) C18 0.025(3) 0.014(3) 0.024(3) -0.005(2) 0.004(3) 0.002(2) C11 0.023(3) 0.014(3) 0.017(3) 0.002(2) 0.006(2) 0.003(2) C2 0.024(3) 0.017(3) 0.031(3) 0.006(3) 0.011(3) 0.001(3) C12 0.012(3) 0.021(3) 0.020(3) -0.001(2) 0.006(2) 0.002(2) C15 0.019(3) 0.030(4) 0.020(3) 0.000(3) 0.007(2) -0.001(3) C1 0.021(3) 0.020(3) 0.021(3) 0.003(2) 0.009(2) -0.001(3) C17 0.020(3) 0.015(3) 0.018(3) 0.003(2) 0.006(2) 0.003(2) C3 0.031(4) 0.014(3) 0.039(4) 0.004(3) 0.022(3) -0.003(3) C4 0.024(3) 0.023(3) 0.018(3) 0.000(2) 0.009(3) -0.004(3) C8 0.016(3) 0.030(4) 0.016(3) -0.004(2) 0.004(2) -0.006(3) C9 0.016(3) 0.032(4) 0.014(3) 0.003(2) 0.002(2) 0.001(3) O100 0.036(3) 0.036(3) 0.024(2) 0.002(2) 0.013(2) 0.000(2) C100 0.028(4) 0.037(4) 0.033(4) -0.006(3) 0.009(3) 0.000(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 Co1 N2 2.113(4) . ? Co1 N1 2.155(5) . ? Co1 N4 2.169(5) . ? Co1 N3 2.212(5) . ? Co1 Cl1 2.4073(15) . ? Co1 Cl2 2.4136(14) . ? C10 N2 1.343(8) . ? C10 C9 1.396(8) . ? C10 C11 1.501(8) . ? C13 N4 1.326(7) . ? C13 C14 1.383(8) . ? C13 C12 1.509(8) . ? N2 C6 1.334(7) . ? N4 C17 1.332(7) . ? N3 C18 1.487(7) . ? N3 C12 1.495(7) . ? N3 C11 1.501(7) . ? C5 N1 1.354(7) . ? C5 C4 1.408(9) . ? C5 C6 1.479(8) . ? C14 C15 1.373(8) . ? C16 C17 1.385(8) . ? C16 C15 1.387(9) . ? C7 C8 1.388(9) . ? C7 C6 1.395(8) . ? N1 C1 1.321(7) . ? C2 C3 1.390(9) . ? C2 C1 1.405(9) . ? C3 C4 1.380(9) . ? C8 C9 1.386(9) . ? O100 C100 1.424(8) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N2 Co1 N1 74.34(18) . . ? N2 Co1 N4 98.14(17) . . ? N1 Co1 N4 91.23(18) . . ? N2 Co1 N3 74.59(17) . . ? N1 Co1 N3 144.71(18) . . ? N4 Co1 N3 77.04(18) . . ? N2 Co1 Cl1 175.07(13) . . ? N1 Co1 Cl1 103.51(13) . . ? N4 Co1 Cl1 86.29(12) . . ? N3 Co1 Cl1 108.69(13) . . ? N2 Co1 Cl2 85.99(13) . . ? N1 Co1 Cl2 98.49(12) . . ? N4 Co1 Cl2 170.16(14) . . ? N3 Co1 Cl2 95.61(13) . . ? Cl1 Co1 Cl2 89.97(5) . . ? N2 C10 C9 121.2(6) . . ? N2 C10 C11 113.5(5) . . ? C9 C10 C11 125.4(5) . . ? N4 C13 C14 123.3(5) . . ? N4 C13 C12 116.5(5) . . ? C14 C13 C12 120.1(5) . . ? C6 N2 C10 121.1(5) . . ? C6 N2 Co1 120.5(4) . . ? C10 N2 Co1 118.4(4) . . ? C13 N4 C17 118.9(5) . . ? C13 N4 Co1 117.3(4) . . ? C17 N4 Co1 123.6(4) . . ? C18 N3 C12 111.5(4) . . ? C18 N3 C11 110.4(4) . . ? C12 N3 C11 109.4(4) . . ? C18 N3 Co1 110.4(3) . . ? C12 N3 Co1 109.5(3) . . ? C11 N3 Co1 105.5(3) . . ? N1 C5 C4 122.2(5) . . ? N1 C5 C6 115.2(5) . . ? C4 C5 C6 122.5(5) . . ? C15 C14 C13 117.8(6) . . ? C17 C16 C15 118.6(6) . . ? C8 C7 C6 119.4(5) . . ? C1 N1 C5 119.3(5) . . ? C1 N1 Co1 123.5(4) . . ? C5 N1 Co1 116.9(4) . . ? N2 C6 C7 120.3(5) . . ? N2 C6 C5 113.0(5) . . ? C7 C6 C5 126.6(5) . . ? N3 C11 C10 107.7(4) . . ? C3 C2 C1 118.4(6) . . ? N3 C12 C13 112.0(4) . . ? C14 C15 C16 119.6(6) . . ? N1 C1 C2 122.2(6) . . ? N4 C17 C16 121.8(5) . . ? C4 C3 C2 120.2(6) . . ? C3 C4 C5 117.7(5) . . ? C9 C8 C7 119.5(5) . . ? C8 C9 C10 118.4(6) . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 26.42 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.976 _refine_diff_density_min -1.899 _refine_diff_density_rms 0.376 _database_code_depnum_ccdc_archive 'CCDC 945155'