# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2002 data_global _journal_coden_Cambridge 182 loop_ _publ_author_name 'Joel Miller' 'Christopher Incarvito' 'Shireen R.Marshall' 'Arnold Rheingold' 'William W.Shum' _publ_contact_author_name 'Prof Joel Miller' _publ_contact_author_address ; Department of Chemistry University of Utah 315 S. 1400 E. RM 2124 Salt Lake City UT 84112-0850 UNITED STATES OF AMERICA ; _publ_contact_author_email 'JSMILLER@CHEM.UTAH.EDU' _publ_requested_journal 'Chemical Communications' _publ_section_title ; Novel Coordination of Dicyanamide, [N(CN)2]-: Preferential Binding of the Amide Nitrogen ; data_CoH2biim(N(CN)2 _database_code_CSD 193518 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H12 Co N14' _chemical_formula_weight 459.33 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' 'Co' 'Co' 0.3494 0.9721 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.1616(10) _cell_length_b 7.6838(10) _cell_length_c 9.1417(12) _cell_angle_alpha 97.338(2) _cell_angle_beta 108.909(2) _cell_angle_gamma 94.916(2) _cell_volume 467.66(11) _cell_formula_units_Z 1 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 954 _cell_measurement_theta_min 3.03 _cell_measurement_theta_max 27.90 _exptl_crystal_description block _exptl_crystal_colour orange _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.631 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 233 _exptl_absorpt_coefficient_mu 0.957 _exptl_absorpt_correction_type SADABS _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 5310 _diffrn_reflns_av_R_equivalents 0.0186 _diffrn_reflns_av_sigmaI/netI 0.0218 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.39 _diffrn_reflns_theta_max 28.25 _reflns_number_total 2140 _reflns_number_gt 2061 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _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^)+(0.1000P)^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 2140 _refine_ls_number_parameters 150 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0307 _refine_ls_R_factor_gt 0.0299 _refine_ls_wR_factor_ref 0.1075 _refine_ls_wR_factor_gt 0.1061 _refine_ls_goodness_of_fit_ref 0.973 _refine_ls_restrained_S_all 0.977 _refine_ls_shift/su_max 0.016 _refine_ls_shift/su_mean 0.001 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Co1 Co 0.5000 0.5000 1.0000 0.01720(14) Uani 1 2 d S . . N1 N 0.31715(18) 0.36598(17) 0.77116(14) 0.0192(3) Uani 1 1 d . . . N2 N 0.2025(2) 0.37872(18) 0.51918(16) 0.0218(3) Uani 1 1 d D . . H2 H 0.192(3) 0.412(3) 0.460(3) 0.020(6) Uiso 1 1 d D . . N3 N 0.46983(19) 0.30624(16) 1.14040(14) 0.0197(3) Uani 1 1 d . . . N4 N 0.4328(2) 0.76972(18) 0.62522(16) 0.0235(3) Uani 1 1 d D . . H4 H 0.369(3) 0.744(3) 0.527(3) 0.035(6) Uiso 1 1 d D . . N5 N 0.24550(19) 0.61807(17) 1.03267(14) 0.0219(3) Uani 1 1 d . . . N6 N 0.0546(2) 0.7763(2) 0.82469(17) 0.0320(3) Uani 1 1 d . . . N7 N 0.2269(2) 0.6422(2) 1.29905(16) 0.0276(3) Uani 1 1 d . . . C1 C 0.2081(2) 0.2060(2) 0.69261(18) 0.0229(3) Uani 1 1 d . . . H1A H 0.1862 0.1066 0.7399 0.028 Uiso 1 1 calc R . . C2 C 0.1362(3) 0.2122(2) 0.53595(19) 0.0265(4) Uani 1 1 d . . . H2A H 0.0562 0.1197 0.4549 0.032 Uiso 1 1 calc R . . C3 C 0.3114(2) 0.4667(2) 0.66257(17) 0.0187(3) Uani 1 1 d . . . C4 C 0.4210(2) 0.64133(19) 0.71039(16) 0.0187(3) Uani 1 1 d . . . C5 C 0.3838(2) 0.1365(2) 1.12910(19) 0.0237(3) Uani 1 1 d . . . H5A H 0.2970 0.0641 1.0355 0.028 Uiso 1 1 calc R . . C6 C 0.4433(3) 0.0880(2) 1.2744(2) 0.0275(4) Uani 1 1 d . . . H6A H 0.4059 -0.0224 1.3005 0.033 Uiso 1 1 calc R . . C7 C 0.1369(2) 0.7048(2) 0.92549(17) 0.0220(3) Uani 1 1 d . . . C8 C 0.2269(2) 0.63495(19) 1.17199(18) 0.0211(3) Uani 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 Co1 0.0217(2) 0.01746(19) 0.0095(2) 0.00310(12) 0.00172(13) 0.00013(12) N1 0.0233(6) 0.0203(6) 0.0120(6) 0.0045(5) 0.0029(5) 0.0017(5) N2 0.0289(7) 0.0231(7) 0.0097(6) 0.0050(5) 0.0016(5) 0.0003(5) N3 0.0239(6) 0.0192(6) 0.0134(7) 0.0032(5) 0.0034(5) 0.0006(5) N4 0.0330(7) 0.0228(6) 0.0140(6) 0.0069(5) 0.0061(5) 0.0024(5) N5 0.0253(6) 0.0267(6) 0.0127(6) 0.0057(5) 0.0040(5) 0.0047(5) N6 0.0357(8) 0.0424(9) 0.0185(7) 0.0109(6) 0.0058(6) 0.0124(7) N7 0.0345(7) 0.0338(8) 0.0153(7) 0.0080(5) 0.0076(5) 0.0069(6) C1 0.0281(7) 0.0208(7) 0.0156(7) 0.0041(6) 0.0024(6) -0.0014(6) C2 0.0327(8) 0.0241(8) 0.0161(8) 0.0014(6) 0.0019(6) -0.0041(6) C3 0.0221(7) 0.0207(7) 0.0121(7) 0.0043(5) 0.0039(5) 0.0024(5) C4 0.0237(7) 0.0196(7) 0.0130(7) 0.0050(5) 0.0053(5) 0.0041(5) C5 0.0290(8) 0.0191(7) 0.0203(7) 0.0034(6) 0.0060(6) -0.0014(6) C6 0.0373(9) 0.0217(7) 0.0228(8) 0.0080(6) 0.0090(7) -0.0006(7) C7 0.0249(7) 0.0242(7) 0.0150(7) 0.0013(6) 0.0053(6) 0.0010(6) C8 0.0223(7) 0.0186(7) 0.0195(7) 0.0035(5) 0.0034(6) 0.0008(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 Co1 N3 2.1268(12) . ? Co1 N3 2.1268(12) 2_667 ? Co1 N1 2.1435(12) . ? Co1 N1 2.1435(12) 2_667 ? Co1 N5 2.1912(13) 2_667 ? Co1 N5 2.1912(13) . ? N1 C3 1.3269(18) . ? N1 C1 1.3720(19) . ? N2 H2 0.62(2) . ? N2 C3 1.343(2) . ? N2 C2 1.371(2) . ? N3 C4 1.3224(19) 2_667 ? N3 C5 1.370(2) . ? N4 H4 0.85(2) . ? N4 C4 1.3459(19) . ? N4 C6 1.369(2) 2_667 ? N5 C8 1.3143(19) . ? N5 C7 1.3307(18) . ? N6 C7 1.154(2) . ? N7 C8 1.156(2) . ? C1 C2 1.364(2) . ? C3 C4 1.434(2) . ? C4 N3 1.3224(19) 2_667 ? C5 C6 1.368(2) . ? C6 N4 1.369(2) 2_667 ? 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 N3 Co1 N3 180.0 . 2_667 ? N3 Co1 N1 101.21(5) . . ? N3 Co1 N1 78.79(5) 2_667 . ? N3 Co1 N1 78.79(5) . 2_667 ? N3 Co1 N1 101.21(5) 2_667 2_667 ? N1 Co1 N1 180.0 . 2_667 ? N3 Co1 N5 88.74(5) . 2_667 ? N3 Co1 N5 91.26(5) 2_667 2_667 ? N1 Co1 N5 89.29(5) . 2_667 ? N1 Co1 N5 90.71(5) 2_667 2_667 ? N3 Co1 N5 91.26(5) . . ? N3 Co1 N5 88.74(5) 2_667 . ? N1 Co1 N5 90.71(5) . . ? N1 Co1 N5 89.29(5) 2_667 . ? N5 Co1 N5 180.000(1) 2_667 . ? C3 N1 C1 106.07(12) . . ? C3 N1 Co1 111.54(9) . . ? C1 N1 Co1 142.29(10) . . ? H2 N2 C3 122(2) . . ? H2 N2 C2 130(2) . . ? C3 N2 C2 107.61(13) . . ? C4 N3 C5 106.29(12) 2_667 . ? C4 N3 Co1 111.98(10) 2_667 . ? C5 N3 Co1 141.56(10) . . ? H4 N4 C4 116.3(15) . . ? H4 N4 C6 136.4(16) . 2_667 ? C4 N4 C6 107.30(14) . 2_667 ? C8 N5 C7 119.27(13) . . ? C8 N5 Co1 118.72(10) . . ? C7 N5 Co1 120.47(10) . . ? C2 C1 N1 109.31(14) . . ? C1 C2 N2 106.12(14) . . ? N1 C3 N2 110.89(13) . . ? N1 C3 C4 118.58(12) . . ? N2 C3 C4 130.50(13) . . ? N3 C4 N4 111.05(13) 2_667 . ? N3 C4 C3 119.02(12) 2_667 . ? N4 C4 C3 129.93(13) . . ? C6 C5 N3 108.99(14) . . ? C5 C6 N4 106.37(14) . 2_667 ? N6 C7 N5 173.51(16) . . ? N7 C8 N5 173.45(16) . . ? _diffrn_measured_fraction_theta_max 0.923 _diffrn_reflns_theta_full 28.25 _diffrn_measured_fraction_theta_full 0.923 _refine_diff_density_max 0.464 _refine_diff_density_min -0.271 _refine_diff_density_rms 0.066 data_[Co(H2biIm)2(µ-N(CN)2)]Cl _database_code_CSD 193519 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H12 Cl Co N11' _chemical_formula_weight 428.73 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' '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 P2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 7.9690(5) _cell_length_b 13.8284(9) _cell_length_c 8.1547(5) _cell_angle_alpha 90.00 _cell_angle_beta 110.5790(10) _cell_angle_gamma 90.00 _cell_volume 841.29(9) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 4702 _cell_measurement_theta_min 2.67 _cell_measurement_theta_max 28.26 _exptl_crystal_description PLATE _exptl_crystal_colour ORANGE _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.692 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 434 _exptl_absorpt_coefficient_mu 1.206 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.7137 _exptl_absorpt_correction_T_max 0.8889 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 5359 _diffrn_reflns_av_R_equivalents 0.0162 _diffrn_reflns_av_sigmaI/netI 0.0419 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -6 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 2.67 _diffrn_reflns_theta_max 28.26 _reflns_number_total 3644 _reflns_number_gt 3525 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _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^)+(0.0360P)^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 0.804(10) _refine_ls_number_reflns 3644 _refine_ls_number_parameters 245 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0276 _refine_ls_R_factor_gt 0.0268 _refine_ls_wR_factor_ref 0.0679 _refine_ls_wR_factor_gt 0.0676 _refine_ls_goodness_of_fit_ref 1.033 _refine_ls_restrained_S_all 1.033 _refine_ls_shift/su_max 0.005 _refine_ls_shift/su_mean 0.001 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 0.14569(3) 0.276834(16) 0.09569(3) 0.01544(8) Uani 1 1 d . . . Cl1 Cl -0.34378(7) 0.25488(5) -0.39172(7) 0.03009(19) Uani 1 1 d . . . N1 N 0.1288(2) 0.34159(13) 0.3275(2) 0.0182(4) Uani 1 1 d . . . N2 N -0.0215(3) 0.35089(14) 0.5093(3) 0.0197(4) Uani 1 1 d . . . H2A H -0.1027 0.3392 0.5572 0.024 Uiso 1 1 calc R . . N3 N -0.0833(2) 0.20253(13) 0.1188(2) 0.0176(4) Uani 1 1 d . . . N4 N -0.2650(2) 0.18848(13) 0.2700(2) 0.0183(4) Uani 1 1 d . . . H4A H -0.3129 0.1986 0.3507 0.022 Uiso 1 1 calc R . . N5 N 0.1622(2) 0.20577(13) -0.1309(2) 0.0166(4) Uani 1 1 d . . . N6 N 0.3192(2) 0.18662(14) -0.3053(2) 0.0197(4) Uani 1 1 d . . . H6A H 0.4027 0.1950 -0.3516 0.024 Uiso 1 1 calc R . . N7 N 0.3768(2) 0.34481(13) 0.0731(2) 0.0172(4) Uani 1 1 d . . . N8 N 0.5654(2) 0.35056(14) -0.0704(2) 0.0187(4) Uani 1 1 d . . . H8A H 0.6148 0.3378 -0.1490 0.022 Uiso 1 1 calc R . . N9 N 0.3130(2) 0.15797(14) 0.2429(2) 0.0222(4) Uani 1 1 d . . . N10 N 0.2065(3) -0.00319(16) 0.2874(3) 0.0328(5) Uani 1 1 d . . . N11 N 0.0144(2) -0.11154(14) 0.0587(2) 0.0215(4) Uani 1 1 d . . . C1 C 0.2075(3) 0.40961(16) 0.4536(3) 0.0211(4) Uani 1 1 d . . . H1A H 0.3104 0.4465 0.4607 0.025 Uiso 1 1 calc R . . C2 C 0.1171(3) 0.41652(19) 0.5669(3) 0.0227(5) Uani 1 1 d . . . H2B H 0.1440 0.4581 0.6655 0.027 Uiso 1 1 calc R . . C3 C -0.0089(3) 0.30809(15) 0.3660(3) 0.0174(4) Uani 1 1 d . . . C4 C -0.1211(3) 0.23340(15) 0.2556(3) 0.0159(4) Uani 1 1 d . . . C5 C -0.3224(3) 0.12349(19) 0.1338(4) 0.0212(5) Uani 1 1 d . . . H5A H -0.4215 0.0806 0.1084 0.025 Uiso 1 1 calc R . . C6 C -0.2094(3) 0.13285(16) 0.0428(3) 0.0195(4) Uani 1 1 d . . . H6B H -0.2167 0.0966 -0.0584 0.023 Uiso 1 1 calc R . . C7 C 0.0849(3) 0.13420(16) -0.2513(3) 0.0192(4) Uani 1 1 d . . . H7A H -0.0194 0.0987 -0.2582 0.023 Uiso 1 1 calc R . . C8 C 0.1811(3) 0.12205(18) -0.3592(3) 0.0206(5) Uani 1 1 d . . . H8B H 0.1566 0.0774 -0.4533 0.025 Uiso 1 1 calc R . . C9 C 0.3038(3) 0.23511(16) -0.1677(3) 0.0166(4) Uani 1 1 d . . . C10 C 0.4169(3) 0.30996(15) -0.0594(3) 0.0170(4) Uani 1 1 d . . . C11 C 0.6258(3) 0.41624(18) 0.0650(3) 0.0207(5) Uani 1 1 d . . . H11A H 0.7287 0.4564 0.0922 0.025 Uiso 1 1 calc R . . C12 C 0.5081(3) 0.41180(15) 0.1517(3) 0.0194(4) Uani 1 1 d . . . H12A H 0.5155 0.4493 0.2515 0.023 Uiso 1 1 calc R . . C13 C 0.2599(3) 0.08113(17) 0.2554(3) 0.0195(4) Uani 1 1 d . . . C14 C 0.1042(3) -0.05716(15) 0.1590(3) 0.0208(5) Uani 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 Co1 0.01653(13) 0.01649(13) 0.01674(13) -0.00105(11) 0.01014(9) -0.00095(11) Cl1 0.0232(3) 0.0486(5) 0.0242(3) -0.0113(3) 0.0156(2) -0.0097(2) N1 0.0194(8) 0.0211(9) 0.0166(9) -0.0019(7) 0.0093(7) -0.0027(7) N2 0.0212(9) 0.0245(9) 0.0179(9) -0.0030(7) 0.0124(7) -0.0009(7) N3 0.0175(8) 0.0197(9) 0.0177(9) -0.0014(7) 0.0089(7) 0.0008(7) N4 0.0177(9) 0.0233(9) 0.0186(9) -0.0011(7) 0.0120(7) -0.0019(7) N5 0.0169(8) 0.0168(8) 0.0167(9) 0.0009(7) 0.0068(7) -0.0004(7) N6 0.0193(9) 0.0261(9) 0.0177(9) -0.0034(7) 0.0116(7) -0.0022(7) N7 0.0182(8) 0.0169(8) 0.0190(9) -0.0005(7) 0.0097(7) -0.0004(7) N8 0.0176(8) 0.0232(9) 0.0191(9) -0.0026(7) 0.0110(7) -0.0035(7) N9 0.0221(9) 0.0226(10) 0.0228(10) 0.0009(8) 0.0091(8) -0.0017(8) N10 0.0511(14) 0.0259(10) 0.0222(11) -0.0021(8) 0.0140(10) -0.0130(9) N11 0.0238(9) 0.0208(9) 0.0233(10) -0.0004(8) 0.0127(8) -0.0018(8) C1 0.0206(11) 0.0216(10) 0.0223(11) -0.0066(9) 0.0092(9) -0.0053(9) C2 0.0253(11) 0.0247(13) 0.0204(11) -0.0059(10) 0.0110(9) -0.0044(10) C3 0.0169(9) 0.0195(10) 0.0174(10) 0.0005(8) 0.0081(8) 0.0011(8) C4 0.0161(9) 0.0165(9) 0.0171(10) -0.0002(8) 0.0082(8) 0.0012(8) C5 0.0198(10) 0.0203(12) 0.0245(12) -0.0018(10) 0.0091(9) -0.0034(10) C6 0.0193(10) 0.0190(10) 0.0219(11) -0.0021(8) 0.0092(9) 0.0003(8) C7 0.0188(10) 0.0201(10) 0.0201(11) -0.0015(8) 0.0087(8) -0.0011(9) C8 0.0245(11) 0.0204(11) 0.0188(11) -0.0033(10) 0.0101(9) -0.0005(10) C9 0.0176(10) 0.0182(10) 0.0157(10) 0.0019(8) 0.0078(8) 0.0012(8) C10 0.0164(9) 0.0174(9) 0.0190(10) 0.0018(8) 0.0085(8) 0.0013(8) C11 0.0195(11) 0.0188(12) 0.0258(12) -0.0022(10) 0.0107(9) -0.0021(9) C12 0.0225(11) 0.0189(10) 0.0191(11) -0.0032(9) 0.0101(9) -0.0012(9) C13 0.0197(10) 0.0269(11) 0.0132(10) -0.0021(8) 0.0075(8) 0.0010(9) C14 0.0292(12) 0.0164(10) 0.0234(12) 0.0032(9) 0.0173(10) 0.0022(9) _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 N11 2.1133(19) 2 ? Co1 N7 2.1325(18) . ? Co1 N1 2.1386(18) . ? Co1 N5 2.1372(18) . ? Co1 N3 2.1593(18) . ? Co1 N9 2.1900(19) . ? N1 C3 1.326(3) . ? N1 C1 1.372(3) . ? N2 C3 1.345(3) . ? N2 C2 1.378(3) . ? N3 C4 1.324(3) . ? N3 C6 1.373(3) . ? N4 C4 1.345(3) . ? N4 C5 1.376(3) . ? N5 C9 1.329(3) . ? N5 C7 1.378(3) . ? N6 C9 1.350(3) . ? N6 C8 1.365(3) . ? N7 C10 1.321(3) . ? N7 C12 1.375(3) . ? N8 C10 1.341(3) . ? N8 C11 1.380(3) . ? N9 C13 1.162(3) . ? N10 C13 1.299(3) . ? N10 C14 1.311(3) . ? N11 C14 1.155(3) . ? N11 Co1 2.1133(19) 2_545 ? C1 C2 1.360(3) . ? C3 C4 1.453(3) . ? C5 C6 1.359(3) . ? C7 C8 1.365(3) . ? C9 C10 1.450(3) . ? C11 C12 1.359(3) . ? 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 N11 Co1 N7 89.17(7) 2 . ? N11 Co1 N1 90.47(7) 2 . ? N7 Co1 N1 102.50(7) . . ? N11 Co1 N5 91.64(7) 2 . ? N7 Co1 N5 79.09(7) . . ? N1 Co1 N5 177.38(7) . . ? N11 Co1 N3 92.74(7) 2 . ? N7 Co1 N3 177.74(7) . . ? N1 Co1 N3 78.72(7) . . ? N5 Co1 N3 99.63(7) . . ? N11 Co1 N9 176.94(7) 2 . ? N7 Co1 N9 90.01(7) . . ? N1 Co1 N9 92.58(7) . . ? N5 Co1 N9 85.31(7) . . ? N3 Co1 N9 88.02(7) . . ? C3 N1 C1 105.13(18) . . ? C3 N1 Co1 112.16(15) . . ? C1 N1 Co1 142.67(15) . . ? C3 N2 C2 106.86(19) . . ? C4 N3 C6 105.01(17) . . ? C4 N3 Co1 111.68(14) . . ? C6 N3 Co1 143.30(15) . . ? C4 N4 C5 106.43(18) . . ? C9 N5 C7 105.11(18) . . ? C9 N5 Co1 111.72(15) . . ? C7 N5 Co1 143.00(15) . . ? C9 N6 C8 107.08(18) . . ? C10 N7 C12 105.28(18) . . ? C10 N7 Co1 111.98(14) . . ? C12 N7 Co1 142.69(15) . . ? C10 N8 C11 106.83(18) . . ? C13 N9 Co1 124.34(16) . . ? C13 N10 C14 120.4(2) . . ? C14 N11 Co1 172.32(17) . 2_545 ? C2 C1 N1 110.2(2) . . ? C1 C2 N2 106.0(2) . . ? N1 C3 N2 111.87(19) . . ? N1 C3 C4 118.81(19) . . ? N2 C3 C4 129.32(19) . . ? N3 C4 N4 112.22(19) . . ? N3 C4 C3 118.59(18) . . ? N4 C4 C3 129.19(19) . . ? C6 C5 N4 106.4(2) . . ? C5 C6 N3 109.9(2) . . ? C8 C7 N5 109.7(2) . . ? N6 C8 C7 106.5(2) . . ? N5 C9 N6 111.66(19) . . ? N5 C9 C10 118.4(2) . . ? N6 C9 C10 129.93(19) . . ? N7 C10 N8 112.0(2) . . ? N7 C10 C9 118.76(19) . . ? N8 C10 C9 129.2(2) . . ? C12 C11 N8 106.0(2) . . ? C11 C12 N7 109.83(19) . . ? N9 C13 N10 173.8(2) . . ? N11 C14 N10 173.0(2) . . ? _diffrn_measured_fraction_theta_max 0.929 _diffrn_reflns_theta_full 28.26 _diffrn_measured_fraction_theta_full 0.929 _refine_diff_density_max 0.858 _refine_diff_density_min -0.271 _refine_diff_density_rms 0.065