# Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2001 # CCDC Number: 186/2270 data_global # SUBMISSION DETAILS _publ_contact_author_name 'Dr Elisabeth Bouwman' _publ_contact_author_address ; Leiden Institute of Chemistry Gorlaeus Laboratories Leiden University PO Box 9502 2300 RA Leiden The Netherlands ; _publ_contact_author_email bouwman@chem.leidenuniv.nl _publ_contact_author_fax '(071) 527 4451' _publ_contact_author_phone '(071) 527 4450' _publ_contact_letter ; The following structures related to the manuscript submitted to Dalton: Cobalt(II) aldoxime complexes are stabilised by halide hydrogen-bonding: Crystal Structures of [Co{HO-N=C(H)(Me)}~4~X~2~] (X = Cl, Br) and [Co{HO-N=C(H)(Pr)}~4~Cl~2~]. Manuscript number: B007919G The main crystallisation solvent used was methanol. The hydrogen atoms involved in inter and intra molecular hydrogen bonding, were located in the difference Fourier and their displacement parameters allowed to refined freely. All other hydrogen atoms were constrained to have U~iso~ = 1.2Ueq of parent atom. ; _publ_requested_journal 'Dalton' _publ_requested_category ? _publ_requested_coeditor_name ? # TITLE AND AUTHOR LIST _publ_section_title ; Cobalt(II) aldoxime complexes are stabilised by halide hydrogen-bonding: Crystal Structures of [Co{HO-N=C(H)(Me)}~4~X~2~] (X = Cl, Br) and [Co{HO-N=C(H)(Pr)}~4~Cl~2~] ; _publ_section_title_footnote ; ? ; # The loop structure below should contain the names and addresses of all # authors, in the required order of publication. Repeat as necessary. loop_ _publ_author_name _publ_author_footnote _publ_author_address 'Hierso, Jean-Cyrille' ;? ; ; Leiden Institute of Chemistry Gorlaeus Laboratories Leiden University PO Box 9502 2300 RA Leiden The Netherlands ; 'Bouwman, Elisabeth' ;? ; ; Leiden Institute of Chemistry Gorlaeus Laboratories Leiden University PO Box 9502 2300 RA Leiden The Netherlands ; 'Ellis, Dianne D' ;For correspondence concerning the crystallographic studies ; ; Bijvoet Center for Biomolecular Research Department of Crystal and Structural Chemistry Utrecht University Padualaan 8 3584 CH Utrecht The Netherlands ; 'P\'erez Cabero, M\'onica' ;? ; ; Leiden Institute of Chemistry Gorlaeus Laboratories Leiden University PO Box 9502 2300 RA Leiden The Netherlands ; 'Reedijk, Jan' ;? ; ; Leiden Institute of Chemistry Gorlaeus Laboratories Leiden University PO Box 9502 2300 RA Leiden The Netherlands ; 'Spek, Anthony L' ;? ; ; Bijvoet Center for Biomolecular Research Department of Crystal and Structural Chemistry Utrecht University Padualaan 8 3584 CH Utrecht The Netherlands ; #============================================================================== # TEXT _publ_section_synopsis ; ? ; _publ_section_abstract ; ? ; _publ_section_comment ; ? ; _publ_section_acknowledgements ; ? ; _publ_section_references ; Nonius B.V. (1998). Collect. Data Collection Software. Sheldrick, G.M. (1997a). SHELXL97. Program for Crystal Structure Refinement. University of G\"ottingen, Germany. Sheldrick, G.M. (1997b). SHELXS97. Program for Crystal Structure Solution. University of G\"ottingen, Germany. Spek, A.L. (2000). PLATON. A Multipurpose Crystallographic Tool. Utrecht University, The Netherlands. ; _publ_section_figure_captions ; ? ; _publ_section_exptl_prep ; ? ; _publ_section_exptl_refinement ; Diffracted intensities were collected on an Nonius Kappa CCD with rotating anode using graphite-monochromated Mo-Ka X-radiation. The final unit cell dimensions were determined from all reflections. The data were corrected for Lorentz, polarization and absorption effects. Hydrogen atoms, except those on oxygen were constrained to idealized geometries and assigned isotropic displacement paramaters 1.2 times U~iso~ value of their attached carbon atoms. The hydrogen atoms involved in hydrogen bonding were located in the Fourier map and their coordinates and thermal parameters freely refined. ; #============================================================================== data_1 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C16 H36 Cl2 Co N4 O4' _chemical_formula_sum 'C16 H36 Cl2 Co N4 O4' _chemical_formula_weight 478.32 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' 'Cl' 'Cl' 0.1484 0.1585 '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' 'O' 'O' 0.0106 0.0060 '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 7.48640(10) _cell_length_b 12.7386(3) _cell_length_c 12.7471(3) _cell_angle_alpha 84.1284(10) _cell_angle_beta 87.0347(12) _cell_angle_gamma 88.4322(10) _cell_volume 1207.35(4) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description blocks _exptl_crystal_colour pink _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.316 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 506 _exptl_absorpt_coefficient_mu 0.958 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7644 _exptl_absorpt_correction_T_max 0.9507 _exptl_absorpt_process_details 'MULabsCAN in PLATON (Spek, 2000)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 19232 _diffrn_reflns_av_R_equivalents 0.0577 _diffrn_reflns_av_sigmaI/netI 0.0405 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.61 _diffrn_reflns_theta_max 28.00 _reflns_number_total 5798 _reflns_number_gt 5046 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Nonius COLLECT ' _computing_cell_refinement 'DENZO 1.11.0' _computing_data_reduction 'DENZO 1.11.0' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON (Spek, 2000)' _computing_publication_material 'PLATON (Spek, 2000)' _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^)+(0.0219P)^2^+0.4133P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary heavy _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 5798 _refine_ls_number_parameters 267 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0365 _refine_ls_R_factor_gt 0.0294 _refine_ls_wR_factor_ref 0.0727 _refine_ls_wR_factor_gt 0.0694 _refine_ls_goodness_of_fit_ref 1.032 _refine_ls_restrained_S_all 1.032 _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 Co1 Co 0.5000 0.5000 0.5000 0.01952(7) Uani 1 2 d S . . Cl1 Cl 0.79032(4) 0.58788(3) 0.46975(3) 0.02613(9) Uani 1 1 d . . . O10 O 0.47053(17) 0.29453(10) 0.39529(11) 0.0418(3) Uani 1 1 d . . . H10 H 0.385(3) 0.3139(19) 0.4258(19) 0.063(7) Uiso 1 1 d . . . O20 O 0.45261(16) 0.36557(10) 0.71373(10) 0.0383(3) Uani 1 1 d . . . H20 H 0.364(3) 0.3702(17) 0.6804(17) 0.053(6) Uiso 1 1 d . . . N11 N 0.59534(16) 0.36839(9) 0.41662(9) 0.0240(3) Uani 1 1 d . . . N21 N 0.58394(16) 0.41521(9) 0.64514(9) 0.0228(2) Uani 1 1 d . . . C12 C 0.7523(2) 0.34727(12) 0.38083(12) 0.0296(3) Uani 1 1 d . . . H12 H 0.8425 0.3948 0.3935 0.035 Uiso 1 1 calc R . . C13 C 0.8120(2) 0.25655(14) 0.32116(14) 0.0367(4) Uani 1 1 d . . . H13A H 0.8326 0.2820 0.2456 0.044 Uiso 1 1 calc R . . H13B H 0.7160 0.2040 0.3268 0.044 Uiso 1 1 calc R . . C14 C 0.9814(2) 0.20413(14) 0.36219(14) 0.0386(4) Uani 1 1 d . . . H14A H 1.0211 0.1486 0.3167 0.046 Uiso 1 1 calc R . . H14B H 1.0764 0.2572 0.3577 0.046 Uiso 1 1 calc R . . C15 C 0.9580(4) 0.15558(17) 0.47421(17) 0.0705(7) Uani 1 1 d . . . H15A H 0.9242 0.2107 0.5202 0.106 Uiso 1 1 calc R . . H15B H 1.0706 0.1212 0.4963 0.106 Uiso 1 1 calc R . . H15C H 0.8638 0.1031 0.4793 0.106 Uiso 1 1 calc R . . C22 C 0.7397(2) 0.39919(11) 0.67942(12) 0.0264(3) Uani 1 1 d . . . H22 H 0.8357 0.4326 0.6385 0.032 Uiso 1 1 calc R . . C23 C 0.7855(2) 0.33281(13) 0.77795(13) 0.0337(4) Uani 1 1 d . . . H23A H 0.7592 0.2583 0.7702 0.040 Uiso 1 1 calc R . . H23B H 0.7085 0.3551 0.8375 0.040 Uiso 1 1 calc R . . C24 C 0.9797(2) 0.33977(14) 0.80413(13) 0.0353(4) Uani 1 1 d . . . H24A H 1.0071 0.2837 0.8610 0.042 Uiso 1 1 calc R . . H24B H 1.0569 0.3269 0.7411 0.042 Uiso 1 1 calc R . . C25 C 1.0230(3) 0.44488(18) 0.83874(19) 0.0630(6) Uani 1 1 d . . . H25A H 0.9980 0.5007 0.7823 0.094 Uiso 1 1 calc R . . H25B H 1.1499 0.4453 0.8542 0.094 Uiso 1 1 calc R . . H25C H 0.9495 0.4572 0.9024 0.094 Uiso 1 1 calc R . . Co2 Co 1.0000 0.0000 0.0000 0.02044(7) Uani 1 2 d S . . Cl2 Cl 0.71019(4) 0.08136(3) -0.04604(3) 0.02533(8) Uani 1 1 d . . . O30 O 0.94009(16) 0.22181(9) 0.06913(10) 0.0338(3) Uani 1 1 d . . . H30 H 0.857(3) 0.1974(18) 0.0475(18) 0.058(7) Uiso 1 1 d . . . O40 O 1.02913(15) -0.06378(10) 0.23625(9) 0.0333(3) Uani 1 1 d . . . H40 H 1.121(3) -0.0665(16) 0.2012(17) 0.050(6) Uiso 1 1 d . . . N31 N 1.07740(16) 0.14841(9) 0.04842(10) 0.0244(3) Uani 1 1 d . . . N41 N 0.90084(16) -0.04428(9) 0.15996(9) 0.0240(3) Uani 1 1 d . . . C32 C 1.2313(2) 0.18138(12) 0.06416(13) 0.0301(3) Uani 1 1 d . . . H32 H 1.3300 0.1349 0.0521 0.036 Uiso 1 1 calc R . . C33 C 1.2730(2) 0.28560(13) 0.09960(15) 0.0373(4) Uani 1 1 d . . . H33A H 1.2029 0.3415 0.0592 0.045 Uiso 1 1 calc R . . H33B H 1.2349 0.2858 0.1751 0.045 Uiso 1 1 calc R . . C34 C 1.4664(2) 0.31102(15) 0.08578(18) 0.0472(5) Uani 1 1 d . . . H34A H 1.5028 0.3150 0.0097 0.057 Uiso 1 1 calc R . . H34B H 1.5370 0.2530 0.1227 0.057 Uiso 1 1 calc R . . C35 C 1.5107(3) 0.41388(15) 0.12749(17) 0.0514(5) Uani 1 1 d . . . H35A H 1.4393 0.4716 0.0926 0.077 Uiso 1 1 calc R . . H35B H 1.6382 0.4278 0.1131 0.077 Uiso 1 1 calc R . . H35C H 1.4833 0.4088 0.2038 0.077 Uiso 1 1 calc R . . C42 C 0.7426(2) -0.05587(12) 0.19981(12) 0.0287(3) Uani 1 1 d . . . H42 H 0.6470 -0.0420 0.1538 0.034 Uiso 1 1 calc R . . C43 C 0.6946(2) -0.08967(13) 0.31356(12) 0.0327(3) Uani 1 1 d . . . H43A H 0.7525 -0.0423 0.3579 0.039 Uiso 1 1 calc R . . H43B H 0.7429 -0.1620 0.3315 0.039 Uiso 1 1 calc R . . C44 C 0.4943(2) -0.08817(13) 0.33998(13) 0.0351(4) Uani 1 1 d . . . H44A H 0.4346 -0.1289 0.2902 0.042 Uiso 1 1 calc R . . H44B H 0.4713 -0.1236 0.4121 0.042 Uiso 1 1 calc R . . C45 C 0.4132(2) 0.02198(15) 0.33436(16) 0.0453(4) Uani 1 1 d . . . H45A H 0.4669 0.0616 0.3862 0.068 Uiso 1 1 calc R . . H45B H 0.2838 0.0181 0.3499 0.068 Uiso 1 1 calc R . . H45C H 0.4362 0.0578 0.2634 0.068 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 0.01738(13) 0.01817(13) 0.02285(14) -0.00167(10) -0.00071(10) 0.00085(10) Cl1 0.01875(16) 0.02726(18) 0.03196(19) -0.00089(14) -0.00046(14) -0.00219(13) O10 0.0307(6) 0.0377(7) 0.0611(9) -0.0269(6) 0.0053(6) -0.0070(5) O20 0.0243(6) 0.0503(8) 0.0367(7) 0.0147(5) -0.0025(5) -0.0096(5) N11 0.0245(6) 0.0217(6) 0.0265(6) -0.0045(5) -0.0030(5) -0.0004(5) N21 0.0228(6) 0.0212(6) 0.0238(6) -0.0004(5) 0.0013(5) -0.0013(5) C12 0.0269(8) 0.0310(8) 0.0319(8) -0.0092(6) -0.0030(6) 0.0046(6) C13 0.0358(9) 0.0407(9) 0.0363(9) -0.0184(7) -0.0043(7) 0.0116(7) C14 0.0337(9) 0.0376(9) 0.0464(10) -0.0144(8) -0.0049(8) 0.0102(7) C15 0.116(2) 0.0454(12) 0.0513(13) -0.0066(10) -0.0238(13) 0.0244(13) C22 0.0243(7) 0.0261(7) 0.0281(8) 0.0014(6) -0.0019(6) -0.0014(6) C23 0.0329(8) 0.0312(8) 0.0356(9) 0.0079(7) -0.0089(7) -0.0047(7) C24 0.0271(8) 0.0453(10) 0.0318(8) 0.0065(7) -0.0055(7) 0.0001(7) C25 0.0645(14) 0.0632(14) 0.0641(14) -0.0041(11) -0.0243(12) -0.0235(12) Co2 0.01786(13) 0.01982(13) 0.02345(14) -0.00068(10) -0.00187(10) -0.00094(10) Cl2 0.01911(16) 0.02560(17) 0.03093(19) -0.00073(14) -0.00311(13) 0.00126(13) O30 0.0253(6) 0.0339(6) 0.0449(7) -0.0181(5) -0.0007(5) 0.0033(5) O40 0.0242(6) 0.0495(7) 0.0257(6) -0.0011(5) -0.0053(5) 0.0027(5) N31 0.0243(6) 0.0222(6) 0.0266(6) -0.0029(5) -0.0007(5) 0.0013(5) N41 0.0224(6) 0.0251(6) 0.0244(6) -0.0012(5) -0.0044(5) 0.0002(5) C32 0.0260(8) 0.0250(7) 0.0400(9) -0.0059(6) -0.0031(7) -0.0009(6) C33 0.0350(9) 0.0293(8) 0.0498(10) -0.0135(7) -0.0018(8) -0.0048(7) C34 0.0378(10) 0.0382(10) 0.0686(13) -0.0193(9) 0.0013(9) -0.0112(8) C35 0.0542(12) 0.0399(10) 0.0636(13) -0.0118(9) -0.0140(10) -0.0172(9) C42 0.0256(7) 0.0330(8) 0.0270(8) 0.0003(6) -0.0027(6) -0.0019(6) C43 0.0312(8) 0.0377(9) 0.0277(8) 0.0015(7) 0.0011(6) 0.0018(7) C44 0.0315(8) 0.0406(9) 0.0328(9) -0.0027(7) 0.0037(7) -0.0053(7) C45 0.0365(9) 0.0497(11) 0.0508(11) -0.0116(9) -0.0023(8) 0.0050(8) _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 N21 2.1584(12) 2_666 ? Co1 N21 2.1585(12) . y Co1 N11 2.1610(12) 2_666 ? Co1 N11 2.1611(12) . y Co1 Cl1 2.4665(3) . y Co1 Cl1 2.4665(3) 2_666 ? O10 N11 1.3997(16) . ? O10 H10 0.78(2) . ? O20 N21 1.4010(16) . ? O20 H20 0.80(2) . ? N11 C12 1.2704(19) . ? N21 C22 1.2700(19) . ? C12 C13 1.493(2) . ? C12 H12 0.9500 . ? C13 C14 1.510(2) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 C15 1.501(3) . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C22 C23 1.491(2) . ? C22 H22 0.9500 . ? C23 C24 1.515(2) . ? C23 H23A 0.9900 . ? C23 H23B 0.9900 . ? C24 C25 1.501(3) . ? C24 H24A 0.9900 . ? C24 H24B 0.9900 . ? C25 H25A 0.9800 . ? C25 H25B 0.9800 . ? C25 H25C 0.9800 . ? Co2 N31 2.1509(12) 2_755 ? Co2 N31 2.1510(12) . y Co2 N41 2.1582(12) 2_755 ? Co2 N41 2.1583(12) . y Co2 Cl2 2.4515(3) 2_755 ? Co2 Cl2 2.4515(3) . y O30 N31 1.4037(16) . ? O30 H30 0.78(2) . ? O40 N41 1.4014(15) . ? O40 H40 0.80(2) . ? N31 C32 1.2697(19) . ? N41 C42 1.2711(19) . ? C32 C33 1.491(2) . ? C32 H32 0.9500 . ? C33 C34 1.490(2) . ? C33 H33A 0.9900 . ? C33 H33B 0.9900 . ? C34 C35 1.515(2) . ? C34 H34A 0.9900 . ? C34 H34B 0.9900 . ? C35 H35A 0.9800 . ? C35 H35B 0.9800 . ? C35 H35C 0.9800 . ? C42 C43 1.498(2) . ? C42 H42 0.9500 . ? C43 C44 1.520(2) . ? C43 H43A 0.9900 . ? C43 H43B 0.9900 . ? C44 C45 1.510(2) . ? C44 H44A 0.9900 . ? C44 H44B 0.9900 . ? C45 H45A 0.9800 . ? C45 H45B 0.9800 . ? C45 H45C 0.9800 . ? 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 N21 Co1 N21 180.00(6) 2_666 . ? N21 Co1 N11 89.06(4) 2_666 2_666 ? N21 Co1 N11 90.94(4) . 2_666 ? N21 Co1 N11 90.95(4) 2_666 . ? N21 Co1 N11 89.05(4) . . y N11 Co1 N11 180.0 2_666 . ? N21 Co1 Cl1 88.37(3) 2_666 . ? N21 Co1 Cl1 91.63(3) . . y N11 Co1 Cl1 88.04(3) 2_666 . ? N11 Co1 Cl1 91.96(3) . . y N21 Co1 Cl1 91.63(3) 2_666 2_666 ? N21 Co1 Cl1 88.37(3) . 2_666 ? N11 Co1 Cl1 91.96(3) 2_666 2_666 ? N11 Co1 Cl1 88.04(3) . 2_666 ? Cl1 Co1 Cl1 180.000(14) . 2_666 ? N11 O10 H10 101.6(17) . . ? N21 O20 H20 104.3(16) . . ? C12 N11 O10 112.74(12) . . ? C12 N11 Co1 129.37(11) . . ? O10 N11 Co1 117.88(9) . . ? C22 N21 O20 111.98(12) . . ? C22 N21 Co1 130.00(10) . . ? O20 N21 Co1 117.98(9) . . ? N11 C12 C13 127.70(15) . . ? N11 C12 H12 116.1 . . ? C13 C12 H12 116.1 . . ? C12 C13 C14 111.99(14) . . ? C12 C13 H13A 109.2 . . ? C14 C13 H13A 109.2 . . ? C12 C13 H13B 109.2 . . ? C14 C13 H13B 109.2 . . ? H13A C13 H13B 107.9 . . ? C15 C14 C13 112.78(17) . . ? C15 C14 H14A 109.0 . . ? C13 C14 H14A 109.0 . . ? C15 C14 H14B 109.0 . . ? C13 C14 H14B 109.0 . . ? H14A C14 H14B 107.8 . . ? C14 C15 H15A 109.5 . . ? C14 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C14 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? N21 C22 C23 125.98(14) . . ? N21 C22 H22 117.0 . . ? C23 C22 H22 117.0 . . ? C22 C23 C24 113.30(13) . . ? C22 C23 H23A 108.9 . . ? C24 C23 H23A 108.9 . . ? C22 C23 H23B 108.9 . . ? C24 C23 H23B 108.9 . . ? H23A C23 H23B 107.7 . . ? C25 C24 C23 112.78(16) . . ? C25 C24 H24A 109.0 . . ? C23 C24 H24A 109.0 . . ? C25 C24 H24B 109.0 . . ? C23 C24 H24B 109.0 . . ? H24A C24 H24B 107.8 . . ? C24 C25 H25A 109.5 . . ? C24 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? C24 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? N31 Co2 N31 180.0 2_755 . ? N31 Co2 N41 88.64(4) 2_755 2_755 ? N31 Co2 N41 91.37(4) . 2_755 ? N31 Co2 N41 91.37(4) 2_755 . ? N31 Co2 N41 88.63(4) . . y N41 Co2 N41 179.998(1) 2_755 . ? N31 Co2 Cl2 88.81(3) 2_755 2_755 ? N31 Co2 Cl2 91.19(3) . 2_755 ? N41 Co2 Cl2 91.24(3) 2_755 2_755 ? N41 Co2 Cl2 88.76(3) . 2_755 ? N31 Co2 Cl2 91.19(3) 2_755 . ? N31 Co2 Cl2 88.81(3) . . y N41 Co2 Cl2 88.76(3) 2_755 . ? N41 Co2 Cl2 91.24(3) . . y Cl2 Co2 Cl2 180.000(15) 2_755 . ? N31 O30 H30 102.7(17) . . ? N41 O40 H40 102.7(15) . . ? C32 N31 O30 112.62(12) . . ? C32 N31 Co2 130.12(10) . . ? O30 N31 Co2 117.24(9) . . ? C42 N41 O40 111.93(12) . . ? C42 N41 Co2 131.43(10) . . ? O40 N41 Co2 116.64(9) . . ? N31 C32 C33 126.64(14) . . ? N31 C32 H32 116.7 . . ? C33 C32 H32 116.7 . . ? C34 C33 C32 113.32(14) . . ? C34 C33 H33A 108.9 . . ? C32 C33 H33A 108.9 . . ? C34 C33 H33B 108.9 . . ? C32 C33 H33B 108.9 . . ? H33A C33 H33B 107.7 . . ? C33 C34 C35 113.40(16) . . ? C33 C34 H34A 108.9 . . ? C35 C34 H34A 108.9 . . ? C33 C34 H34B 108.9 . . ? C35 C34 H34B 108.9 . . ? H34A C34 H34B 107.7 . . ? C34 C35 H35A 109.5 . . ? C34 C35 H35B 109.5 . . ? H35A C35 H35B 109.5 . . ? C34 C35 H35C 109.5 . . ? H35A C35 H35C 109.5 . . ? H35B C35 H35C 109.5 . . ? N41 C42 C43 125.23(14) . . ? N41 C42 H42 117.4 . . ? C43 C42 H42 117.4 . . ? C42 C43 C44 113.42(14) . . ? C42 C43 H43A 108.9 . . ? C44 C43 H43A 108.9 . . ? C42 C43 H43B 108.9 . . ? C44 C43 H43B 108.9 . . ? H43A C43 H43B 107.7 . . ? C45 C44 C43 113.04(14) . . ? C45 C44 H44A 109.0 . . ? C43 C44 H44A 109.0 . . ? C45 C44 H44B 109.0 . . ? C43 C44 H44B 109.0 . . ? H44A C44 H44B 107.8 . . ? C44 C45 H45A 109.5 . . ? C44 C45 H45B 109.5 . . ? H45A C45 H45B 109.5 . . ? C44 C45 H45C 109.5 . . ? H45A C45 H45C 109.5 . . ? H45B C45 H45C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N21 Co1 N11 C12 95.80(14) 2_666 . . . ? N21 Co1 N11 C12 -84.20(14) . . . . ? N11 Co1 N11 C12 -71(10) 2_666 . . . ? Cl1 Co1 N11 C12 7.40(14) . . . . ? Cl1 Co1 N11 C12 -172.60(14) 2_666 . . . ? N21 Co1 N11 O10 -82.86(11) 2_666 . . . ? N21 Co1 N11 O10 97.14(11) . . . . ? N11 Co1 N11 O10 110(10) 2_666 . . . ? Cl1 Co1 N11 O10 -171.26(10) . . . . ? Cl1 Co1 N11 O10 8.74(10) 2_666 . . . ? N21 Co1 N21 C22 -118(49) 2_666 . . . ? N11 Co1 N21 C22 -104.39(13) 2_666 . . . ? N11 Co1 N21 C22 75.61(13) . . . . ? Cl1 Co1 N21 C22 -16.33(13) . . . . ? Cl1 Co1 N21 C22 163.67(13) 2_666 . . . ? N21 Co1 N21 O20 64(49) 2_666 . . . ? N11 Co1 N21 O20 77.98(10) 2_666 . . . ? N11 Co1 N21 O20 -102.02(10) . . . . ? Cl1 Co1 N21 O20 166.05(9) . . . . ? Cl1 Co1 N21 O20 -13.95(9) 2_666 . . . ? O10 N11 C12 C13 0.3(2) . . . . ? Co1 N11 C12 C13 -178.38(12) . . . . ? N11 C12 C13 C14 -134.17(18) . . . . y C12 C13 C14 C15 63.4(2) . . . . y O20 N21 C22 C23 2.3(2) . . . . ? Co1 N21 C22 C23 -175.42(11) . . . . ? N21 C22 C23 C24 -173.11(15) . . . . y C22 C23 C24 C25 70.2(2) . . . . y N31 Co2 N31 C32 75(10) 2_755 . . . ? N41 Co2 N31 C32 -74.45(14) 2_755 . . . ? N41 Co2 N31 C32 105.55(14) . . . . ? Cl2 Co2 N31 C32 16.82(14) 2_755 . . . ? Cl2 Co2 N31 C32 -163.18(14) . . . . ? N31 Co2 N31 O30 -103(10) 2_755 . . . ? N41 Co2 N31 O30 107.26(10) 2_755 . . . ? N41 Co2 N31 O30 -72.74(10) . . . . ? Cl2 Co2 N31 O30 -161.47(9) 2_755 . . . ? Cl2 Co2 N31 O30 18.53(9) . . . . ? N31 Co2 N41 C42 -70.24(14) 2_755 . . . ? N31 Co2 N41 C42 109.76(14) . . . . ? N41 Co2 N41 C42 150(6) 2_755 . . . ? Cl2 Co2 N41 C42 -159.02(14) 2_755 . . . ? Cl2 Co2 N41 C42 20.98(14) . . . . ? N31 Co2 N41 O40 110.26(9) 2_755 . . . ? N31 Co2 N41 O40 -69.74(9) . . . . ? N41 Co2 N41 O40 -29(6) 2_755 . . . ? Cl2 Co2 N41 O40 21.48(9) 2_755 . . . ? Cl2 Co2 N41 O40 -158.52(9) . . . . ? O30 N31 C32 C33 -0.6(2) . . . . ? Co2 N31 C32 C33 -178.93(13) . . . . ? N31 C32 C33 C34 -166.02(18) . . . . y C32 C33 C34 C35 -176.68(17) . . . . y O40 N41 C42 C43 -1.9(2) . . . . ? Co2 N41 C42 C43 178.59(11) . . . . ? N41 C42 C43 C44 175.36(15) . . . . y C42 C43 C44 C45 -69.09(19) . . . . y 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 _geom_hbond_publ_flag O10 H10 Cl1 0.78(2) 2.26(2) 3.0061(13) 159(2) 2_666 y O20 H20 Cl1 0.80(2) 2.30(2) 3.0376(13) 154(2) 2_666 y O30 H30 Cl2 0.78(2) 2.32(2) 3.0473(13) 155(2) . y O40 H40 Cl2 0.80(2) 2.32(2) 3.0553(13) 154(2) 2_755 y _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 28.00 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.354 _refine_diff_density_min -0.374 _refine_diff_density_rms 0.051 #===END data_4 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C8 H20 Cl2 Co N4 O4' _chemical_formula_sum 'C8 H20 Cl2 Co N4 O4' _chemical_formula_weight 366.11 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' 'Cl' 'Cl' 0.1484 0.1585 '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' 'O' 'O' 0.0106 0.0060 '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 7.4892(2) _cell_length_b 7.7050(3) _cell_length_c 8.6242(3) _cell_angle_alpha 100.6597(14) _cell_angle_beta 115.3716(19) _cell_angle_gamma 107.584(2) _cell_volume 399.06(2) _cell_formula_units_Z 1 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour purple _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.21 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.523 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 189 _exptl_absorpt_coefficient_mu 1.423 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7286 _exptl_absorpt_correction_T_max 0.8184 _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 'rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4206 _diffrn_reflns_av_R_equivalents 0.0417 _diffrn_reflns_av_sigmaI/netI 0.0435 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.81 _diffrn_reflns_theta_max 27.48 _reflns_number_total 1780 _reflns_number_gt 1577 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Nonius COLLECT' _computing_cell_refinement 'DENZO 1.11' _computing_data_reduction 'DENZO 1.11' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON (Spek, 2000)' _computing_publication_material 'PLATON (Spek, 2000)' _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^)+(0.0143P)^2^+0.2196P] 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 SHELXL _refine_ls_extinction_coef 0.039(4) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 1780 _refine_ls_number_parameters 99 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0332 _refine_ls_R_factor_gt 0.0279 _refine_ls_wR_factor_ref 0.0684 _refine_ls_wR_factor_gt 0.0658 _refine_ls_goodness_of_fit_ref 1.044 _refine_ls_restrained_S_all 1.044 _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 Co1 Co 0.5000 0.0000 0.0000 0.01681(13) Uani 1 2 d S . . Cl1 Cl 0.50019(7) 0.24717(7) 0.22301(6) 0.02274(14) Uani 1 1 d . . . O1 O 0.6328(3) 0.4115(2) -0.0230(2) 0.0316(4) Uani 1 1 d . . . H1 H 0.598(4) 0.398(4) 0.052(4) 0.044(8) Uiso 1 1 d . . . O2 O 0.9147(3) -0.0763(3) 0.1534(2) 0.0512(5) Uani 1 1 d . . . H2 H 0.819(5) -0.149(4) 0.053(4) 0.057(9) Uiso 1 1 d . . . N1 N 0.6298(2) 0.2292(2) -0.0874(2) 0.0192(3) Uani 1 1 d . . . N2 N 0.8320(2) 0.0530(2) 0.1955(2) 0.0213(3) Uani 1 1 d . . . C10 C 0.7042(3) 0.2228(3) -0.1946(3) 0.0236(4) Uani 1 1 d . . . H10 H 0.7055 0.1023 -0.2431 0.028 Uiso 1 1 calc R . . C11 C 0.7899(3) 0.3834(3) -0.2527(3) 0.0302(5) Uani 1 1 d . . . H11A H 0.7610 0.4931 -0.2100 0.045 Uiso 1 1 calc R . . H11B H 0.7170 0.3356 -0.3874 0.045 Uiso 1 1 calc R . . H11C H 0.9479 0.4270 -0.1989 0.045 Uiso 1 1 calc R . . C20 C 0.9675(3) 0.1862(3) 0.3533(3) 0.0251(4) Uani 1 1 d . . . H20 H 0.9211 0.2783 0.3927 0.030 Uiso 1 1 calc R . . C21 C 1.1920(3) 0.2130(3) 0.4831(3) 0.0311(5) Uani 1 1 d . . . H21A H 1.1898 0.0857 0.4851 0.047 Uiso 1 1 calc R . . H21B H 1.2428 0.2984 0.6071 0.047 Uiso 1 1 calc R . . H21C H 1.2911 0.2727 0.4426 0.047 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 0.0179(2) 0.0187(2) 0.01392(19) 0.00552(14) 0.00750(15) 0.00939(15) Cl1 0.0282(3) 0.0240(3) 0.0174(2) 0.00532(19) 0.0120(2) 0.0137(2) O1 0.0503(9) 0.0247(8) 0.0408(9) 0.0172(7) 0.0338(8) 0.0229(7) O2 0.0330(9) 0.0621(13) 0.0330(9) -0.0114(9) -0.0006(8) 0.0332(9) N1 0.0188(7) 0.0202(8) 0.0182(7) 0.0068(6) 0.0077(6) 0.0109(6) N2 0.0211(8) 0.0261(9) 0.0205(8) 0.0091(7) 0.0113(7) 0.0134(7) C10 0.0238(9) 0.0263(11) 0.0208(9) 0.0082(8) 0.0113(8) 0.0114(8) C11 0.0290(10) 0.0372(12) 0.0249(10) 0.0137(9) 0.0156(9) 0.0108(9) C20 0.0235(10) 0.0240(10) 0.0221(9) 0.0064(8) 0.0082(8) 0.0100(8) C21 0.0219(10) 0.0359(12) 0.0232(10) 0.0083(9) 0.0053(8) 0.0088(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 N1 2.1711(15) . y Co1 N1 2.1711(15) 2_655 ? Co1 N2 2.1751(14) 2_655 ? Co1 N2 2.1752(14) . y Co1 Cl1 2.4427(4) . y Co1 Cl1 2.4427(4) 2_655 ? O1 N1 1.402(2) . y O1 H1 0.81(3) . y O2 N2 1.392(2) . y O2 H2 0.79(3) . y N1 C10 1.268(2) . y N2 C20 1.267(2) . y C10 C11 1.490(3) . ? C10 H10 0.9500 . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? C20 C21 1.488(3) . ? C20 H20 0.9500 . ? C21 H21A 0.9800 . ? C21 H21B 0.9800 . ? C21 H21C 0.9800 . ? 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 N1 Co1 N1 180.0 . 2_655 y N1 Co1 N2 90.34(5) . 2_655 ? N1 Co1 N2 89.66(5) 2_655 2_655 ? N1 Co1 N2 89.66(5) . . y N1 Co1 N2 90.34(5) 2_655 . y N2 Co1 N2 180.00(9) 2_655 . y N1 Co1 Cl1 87.93(4) . . y N1 Co1 Cl1 92.07(4) 2_655 . ? N2 Co1 Cl1 87.88(4) 2_655 . ? N2 Co1 Cl1 92.12(4) . . y N1 Co1 Cl1 92.07(4) . 2_655 ? N1 Co1 Cl1 87.93(4) 2_655 2_655 ? N2 Co1 Cl1 92.12(4) 2_655 2_655 ? N2 Co1 Cl1 87.88(4) . 2_655 ? Cl1 Co1 Cl1 180.0 . 2_655 y N1 O1 H1 101.2(19) . . y N2 O2 H2 102(2) . . y C10 N1 O1 112.65(15) . . ? C10 N1 Co1 128.89(14) . . ? O1 N1 Co1 118.45(10) . . ? C20 N2 O2 111.88(15) . . ? C20 N2 Co1 129.02(13) . . ? O2 N2 Co1 119.05(12) . . ? N1 C10 C11 127.18(19) . . ? N1 C10 H10 116.4 . . ? C11 C10 H10 116.4 . . ? C10 C11 H11A 109.5 . . ? C10 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C10 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? N2 C20 C21 126.68(19) . . ? N2 C20 H20 116.7 . . ? C21 C20 H20 116.7 . . ? C20 C21 H21A 109.5 . . ? C20 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C20 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 Co1 N1 C10 163(36) 2_655 . . . ? N2 Co1 N1 C10 -101.63(16) 2_655 . . . ? N2 Co1 N1 C10 78.37(16) . . . . ? Cl1 Co1 N1 C10 170.50(16) . . . . ? Cl1 Co1 N1 C10 -9.50(16) 2_655 . . . ? N1 Co1 N1 O1 -18(36) 2_655 . . . ? N2 Co1 N1 O1 77.30(12) 2_655 . . . ? N2 Co1 N1 O1 -102.70(12) . . . . ? Cl1 Co1 N1 O1 -10.57(11) . . . . ? Cl1 Co1 N1 O1 169.43(11) 2_655 . . . ? N1 Co1 N2 C20 79.76(17) . . . . ? N1 Co1 N2 C20 -100.24(17) 2_655 . . . ? N2 Co1 N2 C20 -55(45) 2_655 . . . ? Cl1 Co1 N2 C20 -8.16(16) . . . . ? Cl1 Co1 N2 C20 171.84(16) 2_655 . . . ? N1 Co1 N2 O2 -103.10(15) . . . . ? N1 Co1 N2 O2 76.90(15) 2_655 . . . ? N2 Co1 N2 O2 122(46) 2_655 . . . ? Cl1 Co1 N2 O2 168.98(14) . . . . ? Cl1 Co1 N2 O2 -11.02(14) 2_655 . . . ? O1 N1 C10 C11 0.3(3) . . . . ? Co1 N1 C10 C11 179.30(14) . . . . ? O2 N2 C20 C21 1.4(3) . . . . ? Co1 N2 C20 C21 178.69(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 _geom_hbond_publ_flag O1 H1 Cl1 0.81(3) 2.26(3) 3.0217(15) 158(3) . y O2 H2 Cl1 0.79(3) 2.31(3) 3.0380(17) 155(3) 2_655 y O1 H1 O1 0.81(3) 2.55(3) 2.843(3) 103(2) 2_665 y _diffrn_measured_fraction_theta_max 0.977 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.977 _refine_diff_density_max 0.397 _refine_diff_density_min -0.355 _refine_diff_density_rms 0.062 #===end data_5 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C8 H20 Br2 Co N4 O4' _chemical_formula_sum 'C8 H20 Br2 Co N4 O4' _chemical_formula_weight 455.03 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' 'Br' 'Br' -0.2901 2.4595 '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' '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 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 7.5824(2) _cell_length_b 12.1368(4) _cell_length_c 9.2141(3) _cell_angle_alpha 90.00 _cell_angle_beta 94.7954(17) _cell_angle_gamma 90.00 _cell_volume 844.97(5) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour purple _exptl_crystal_size_max 0.27 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.788 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 450 _exptl_absorpt_coefficient_mu 5.757 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.2828 _exptl_absorpt_correction_T_max 0.3986 _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 'rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6544 _diffrn_reflns_av_R_equivalents 0.0817 _diffrn_reflns_av_sigmaI/netI 0.0520 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.70 _diffrn_reflns_theta_max 27.47 _reflns_number_total 1930 _reflns_number_gt 1714 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Nonius COLLECT' _computing_cell_refinement 'DENZO 1.11' _computing_data_reduction 'DENZO 1.11' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON (Spek, 2000)' _computing_publication_material 'PLATON (Spek, 2000)' _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^)+(0.0173P)^2^+0.3579P] 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 SHELXL _refine_ls_extinction_coef 0.0048(7) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 1930 _refine_ls_number_parameters 99 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0340 _refine_ls_R_factor_gt 0.0287 _refine_ls_wR_factor_ref 0.0701 _refine_ls_wR_factor_gt 0.0676 _refine_ls_goodness_of_fit_ref 1.053 _refine_ls_restrained_S_all 1.053 _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 Co1 Co 0.0000 0.5000 0.5000 0.02090(13) Uani 1 2 d S . . Br1 Br 0.20467(3) 0.43760(2) 0.73303(3) 0.02989(12) Uani 1 1 d . . . O1 O 0.3723(3) 0.4240(2) 0.4281(3) 0.0516(7) Uani 1 1 d . . . H1 H 0.367(5) 0.431(3) 0.501(4) 0.047(12) Uiso 1 1 d . . . O2 O -0.0730(4) 0.2657(2) 0.6049(3) 0.0688(8) Uani 1 1 d . . . H2 H 0.003(5) 0.298(3) 0.653(4) 0.074(14) Uiso 1 1 d . . . N1 N 0.1996(3) 0.43899(16) 0.3670(2) 0.0248(4) Uani 1 1 d . . . N2 N -0.1248(3) 0.33945(17) 0.4947(2) 0.0256(4) Uani 1 1 d . . . C10 C 0.1858(4) 0.4156(2) 0.2323(3) 0.0295(6) Uani 1 1 d . . . H10 H 0.0723 0.4236 0.1815 0.035 Uiso 1 1 calc R . . C11 C 0.3321(4) 0.3766(2) 0.1472(3) 0.0347(6) Uani 1 1 d . . . H11A H 0.4328 0.4271 0.1621 0.052 Uiso 1 1 calc R . . H11B H 0.2911 0.3745 0.0435 0.052 Uiso 1 1 calc R . . H11C H 0.3686 0.3026 0.1798 0.052 Uiso 1 1 calc R . . C20 C -0.2389(4) 0.2976(2) 0.4037(3) 0.0372(6) Uani 1 1 d . . . H20 H -0.2832 0.3437 0.3257 0.045 Uiso 1 1 calc R . . C21 C -0.3116(5) 0.1841(2) 0.4048(4) 0.0489(8) Uani 1 1 d . . . H21A H -0.2379 0.1388 0.4739 0.073 Uiso 1 1 calc R . . H21B H -0.3121 0.1521 0.3071 0.073 Uiso 1 1 calc R . . H21C H -0.4328 0.1863 0.4342 0.073 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 0.0225(2) 0.0194(2) 0.0201(2) 0.00036(17) -0.00223(18) -0.00046(17) Br1 0.03294(18) 0.03138(17) 0.02377(17) 0.00190(10) -0.00696(12) 0.00425(10) O1 0.0259(11) 0.098(2) 0.0293(12) -0.0171(12) -0.0043(9) 0.0108(11) O2 0.094(2) 0.0370(12) 0.0671(16) 0.0268(12) -0.0410(15) -0.0274(14) N1 0.0217(10) 0.0264(11) 0.0255(11) 0.0006(8) -0.0035(9) -0.0008(8) N2 0.0279(11) 0.0222(10) 0.0264(11) 0.0021(8) 0.0007(9) 0.0004(8) C10 0.0326(14) 0.0299(13) 0.0255(14) -0.0025(10) -0.0005(11) 0.0007(11) C11 0.0370(15) 0.0405(15) 0.0266(13) -0.0047(12) 0.0027(12) 0.0039(12) C20 0.0424(16) 0.0288(13) 0.0388(15) 0.0004(12) -0.0070(13) -0.0056(12) C21 0.0518(19) 0.0363(16) 0.058(2) -0.0036(15) -0.0006(16) -0.0162(15) _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 N1 2.157(2) 3_566 ? Co1 N1 2.157(2) . y Co1 N2 2.165(2) 3_566 ? Co1 N2 2.165(2) . y Co1 Br1 2.6524(2) 3_566 ? Co1 Br1 2.6524(2) . y O1 N1 1.393(3) . y O1 H1 0.68(4) . y O2 N2 1.386(3) . y O2 H2 0.81(4) . y N1 C10 1.269(3) . y N2 C20 1.261(3) . y C10 C11 1.488(3) . ? C10 H10 0.9500 . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? C20 C21 1.484(4) . ? C20 H20 0.9500 . ? C21 H21A 0.9800 . ? C21 H21B 0.9800 . ? C21 H21C 0.9800 . ? 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 N1 Co1 N1 180.00(9) 3_566 . y N1 Co1 N2 90.25(7) 3_566 3_566 ? N1 Co1 N2 89.75(7) . 3_566 ? N1 Co1 N2 89.75(7) 3_566 . y N1 Co1 N2 90.25(7) . . y N2 Co1 N2 179.999(1) 3_566 . y N1 Co1 Br1 88.34(6) 3_566 3_566 ? N1 Co1 Br1 91.66(6) . 3_566 ? N2 Co1 Br1 89.22(5) 3_566 3_566 ? N2 Co1 Br1 90.78(5) . 3_566 y N1 Co1 Br1 91.66(6) 3_566 . y N1 Co1 Br1 88.34(6) . . y N2 Co1 Br1 90.78(5) 3_566 . ? N2 Co1 Br1 89.22(5) . . y Br1 Co1 Br1 180.0 3_566 . y N1 O1 H1 105(3) . . y N2 O2 H2 104(3) . . y C10 N1 O1 111.3(2) . . ? C10 N1 Co1 128.92(19) . . ? O1 N1 Co1 119.70(17) . . ? C20 N2 O2 111.3(2) . . ? C20 N2 Co1 130.73(18) . . ? O2 N2 Co1 117.93(16) . . ? N1 C10 C11 125.6(3) . . ? N1 C10 H10 117.2 . . ? C11 C10 H10 117.2 . . ? C10 C11 H11A 109.5 . . ? C10 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C10 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? N2 C20 C21 127.2(3) . . ? N2 C20 H20 116.4 . . ? C21 C20 H20 116.4 . . ? C20 C21 H21A 109.5 . . ? C20 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C20 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 Co1 N1 C10 67(6) 3_566 . . . ? N2 Co1 N1 C10 -106.9(2) 3_566 . . . ? N2 Co1 N1 C10 73.1(2) . . . . ? Br1 Co1 N1 C10 -17.7(2) 3_566 . . . ? Br1 Co1 N1 C10 162.3(2) . . . . ? N1 Co1 N1 O1 -115(6) 3_566 . . . ? N2 Co1 N1 O1 70.91(19) 3_566 . . . ? N2 Co1 N1 O1 -109.09(19) . . . . ? Br1 Co1 N1 O1 160.13(18) 3_566 . . . ? Br1 Co1 N1 O1 -19.87(18) . . . . ? N1 Co1 N2 C20 93.3(3) 3_566 . . . ? N1 Co1 N2 C20 -86.7(3) . . . . ? N2 Co1 N2 C20 -66(5) 3_566 . . . ? Br1 Co1 N2 C20 5.0(2) 3_566 . . . ? Br1 Co1 N2 C20 -175.0(2) . . . . ? N1 Co1 N2 O2 -88.5(2) 3_566 . . . ? N1 Co1 N2 O2 91.5(2) . . . . ? N2 Co1 N2 O2 113(5) 3_566 . . . ? Br1 Co1 N2 O2 -176.9(2) 3_566 . . . ? Br1 Co1 N2 O2 3.1(2) . . . . ? O1 N1 C10 C11 0.2(4) . . . . ? Co1 N1 C10 C11 178.17(19) . . . . ? O2 N2 C20 C21 -1.4(4) . . . . ? Co1 N2 C20 C21 176.8(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 _geom_hbond_publ_flag O1 H1 Br1 0.68(4) 2.55(4) 3.183(2) 154(4) . y O2 H2 Br1 0.81(4) 2.35(4) 3.125(3) 161(4) . y _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 27.47 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.439 _refine_diff_density_min -0.478 _refine_diff_density_rms 0.091