data_2 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H16 Br2 Cl2 Co N2 O2' _chemical_formula_weight 606.00 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Cl' 'Cl' 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Co' 'Co' 0.3494 0.9721 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Br' 'Br' -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 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 12.3186(15) _cell_length_b 22.916(2) _cell_length_c 7.9518(13) _cell_angle_alpha 90.00 _cell_angle_beta 108.83 _cell_angle_gamma 90.00 _cell_volume 2124.6(5) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 2656 _cell_measurement_theta_min 2.8 _cell_measurement_theta_max 24.3 _exptl_crystal_description block _exptl_crystal_colour red _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.17 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.895 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1188 _exptl_absorpt_coefficient_mu 4.841 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.4444 _exptl_absorpt_correction_T_max 0.4933 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(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 1000 CCD area-detector' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8098 _diffrn_reflns_av_R_equivalents 0.0593 _diffrn_reflns_av_sigmaI/netI 0.1468 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -27 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 1.75 _diffrn_reflns_theta_max 25.13 _reflns_number_total 2979 _reflns_number_gt 1478 _reflns_threshold_expression >2sigma(I) _computing_data_collection SMART _computing_cell_refinement SAINT _computing_data_reduction SAINT _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics SHELXTL _computing_publication_material 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^)+(0.0178P)^2^] 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 2979 _refine_ls_number_parameters 262 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1113 _refine_ls_R_factor_gt 0.0434 _refine_ls_wR_factor_ref 0.0813 _refine_ls_wR_factor_gt 0.0694 _refine_ls_goodness_of_fit_ref 0.771 _refine_ls_restrained_S_all 0.771 _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 0.30624(7) 0.07482(3) 0.31137(12) 0.0427(2) Uani 1 1 d . . . N1 N 0.1540(4) 0.09181(18) 0.3380(6) 0.0353(11) Uani 1 1 d . . . N2 N 0.4287(5) 0.0677(2) 0.5388(7) 0.0491(15) Uani 1 1 d . . . O1 O 0.2597(3) 0.00361(16) 0.1841(5) 0.0456(11) Uani 1 1 d . . . O2 O 0.3822(4) 0.12983(16) 0.2121(6) 0.0466(11) Uani 1 1 d . . . Br1 Br 0.25014(6) -0.10479(3) -0.03254(11) 0.0621(2) Uani 1 1 d . . . Br2 Br 0.44385(7) 0.20527(3) -0.04935(11) 0.0728(3) Uani 1 1 d . . . Cl1 Cl -0.14644(17) -0.13659(7) 0.1229(3) 0.0672(5) Uani 1 1 d . . . Cl2 Cl 0.85156(17) 0.21581(8) 0.4899(3) 0.0876(7) Uani 1 1 d . . . C1 C 0.0776(5) -0.0053(2) 0.2353(8) 0.0356(14) Uani 1 1 d . . . C2 C 0.1676(5) -0.0243(2) 0.1695(8) 0.0375(15) Uani 1 1 d . . . C3 C 0.1457(5) -0.0786(2) 0.0804(8) 0.0422(16) Uani 1 1 d . . . C4 C 0.0541(5) -0.1134(2) 0.0683(8) 0.0415(15) Uani 1 1 d . . . H4 H 0.0461 -0.1494 0.0114 0.050 Uiso 1 1 calc R . . C5 C -0.0279(5) -0.0942(2) 0.1430(8) 0.0414(16) Uani 1 1 d . . . C6 C -0.0164(5) -0.0401(2) 0.2227(8) 0.0411(16) Uani 1 1 d . . . H6 H -0.0725 -0.0269 0.2686 0.049 Uiso 1 1 calc R . . C7 C 0.0771(5) 0.0523(2) 0.3103(8) 0.0399(15) Uani 1 1 d . . . H7 H 0.0129 0.0617 0.3420 0.048 Uiso 1 1 calc R . . C8 C 0.1264(6) 0.1470(3) 0.3985(9) 0.0540(19) Uani 1 1 d . . . H8 H 0.0595 0.1473 0.4396 0.065 Uiso 1 1 calc R . . C9 C 0.1474(7) 0.2009(3) 0.3162(12) 0.076(2) Uani 1 1 d . . . H9A H 0.0930 0.2325 0.3034 0.091 Uiso 1 1 calc R . . H9B H 0.1792 0.1976 0.2198 0.091 Uiso 1 1 calc R . . C10 C 0.2229(7) 0.1872(3) 0.4956(11) 0.068(2) Uani 1 1 d . . . H10A H 0.2142 0.2100 0.5935 0.081 Uiso 1 1 calc R . . H10B H 0.3006 0.1749 0.5097 0.081 Uiso 1 1 calc R . . C11 C 0.5582(6) 0.1326(2) 0.4494(10) 0.0459(17) Uani 1 1 d . . . C12 C 0.4873(5) 0.1477(2) 0.2803(8) 0.0363(15) Uani 1 1 d . . . C13 C 0.5353(5) 0.1840(2) 0.1798(8) 0.0428(16) Uani 1 1 d . . . C14 C 0.6443(6) 0.2060(2) 0.2428(9) 0.0445(16) Uani 1 1 d . . . H14 H 0.6716 0.2313 0.1742 0.053 Uiso 1 1 calc R . . C15 C 0.7122(5) 0.1897(3) 0.4096(11) 0.0530(19) Uani 1 1 d . . . C16 C 0.6706(6) 0.1541(3) 0.5120(9) 0.0544(18) Uani 1 1 d . . . H16 H 0.7177 0.1439 0.6253 0.065 Uiso 1 1 calc R . . C17 C 0.5249(6) 0.0940(3) 0.5687(9) 0.0538(18) Uani 1 1 d . . . H17 H 0.5794 0.0876 0.6793 0.065 Uiso 1 1 calc R . . C18 C 0.4300(10) 0.0303(4) 0.7026(16) 0.132(5) Uani 1 1 d . . . H18 H 0.5047 0.0175 0.7826 0.158 Uiso 1 1 calc R . . C19 C 0.3455(11) -0.0065(5) 0.6675(19) 0.153(5) Uani 1 1 d . . . H19A H 0.3598 -0.0443 0.7257 0.183 Uiso 1 1 calc R . . H19B H 0.2911 -0.0068 0.5480 0.183 Uiso 1 1 calc R . . C20 C 0.3482(10) 0.0443(4) 0.7763(14) 0.135(5) Uani 1 1 d . . . H20A H 0.2967 0.0763 0.7251 0.163 Uiso 1 1 calc R . . H20B H 0.3656 0.0388 0.9033 0.163 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 0.0440(6) 0.0424(5) 0.0469(6) -0.0026(4) 0.0217(5) -0.0049(4) N1 0.042(3) 0.034(3) 0.030(3) 0.000(2) 0.011(3) 0.003(2) N2 0.049(4) 0.052(3) 0.054(4) 0.007(3) 0.027(3) -0.005(3) O1 0.042(3) 0.047(3) 0.054(3) -0.010(2) 0.023(3) -0.004(2) O2 0.041(3) 0.054(3) 0.043(3) 0.011(2) 0.011(2) -0.006(2) Br1 0.0617(5) 0.0670(5) 0.0654(6) -0.0216(4) 0.0314(4) 0.0018(4) Br2 0.0731(6) 0.0848(6) 0.0596(6) 0.0292(4) 0.0200(5) -0.0042(4) Cl1 0.0684(13) 0.0585(11) 0.0821(16) -0.0080(10) 0.0344(12) -0.0243(10) Cl2 0.0484(13) 0.1037(16) 0.109(2) -0.0181(13) 0.0232(13) -0.0217(10) C1 0.039(4) 0.035(3) 0.034(4) 0.002(3) 0.012(3) 0.004(3) C2 0.042(4) 0.044(4) 0.030(4) 0.008(3) 0.018(3) 0.006(3) C3 0.049(4) 0.034(3) 0.046(5) -0.001(3) 0.019(4) 0.004(3) C4 0.055(4) 0.030(3) 0.036(4) -0.003(3) 0.011(3) -0.002(3) C5 0.049(4) 0.035(4) 0.041(4) 0.003(3) 0.015(3) -0.003(3) C6 0.038(4) 0.045(4) 0.045(5) 0.006(3) 0.020(4) -0.003(3) C7 0.042(4) 0.041(4) 0.041(4) 0.002(3) 0.019(3) -0.002(3) C8 0.062(5) 0.047(4) 0.064(6) -0.007(3) 0.036(4) -0.004(3) C9 0.111(7) 0.042(4) 0.076(7) 0.009(4) 0.032(6) 0.012(4) C10 0.085(6) 0.043(4) 0.084(7) -0.013(4) 0.039(6) -0.003(4) C11 0.045(4) 0.044(4) 0.050(5) 0.004(3) 0.018(4) 0.007(3) C12 0.035(4) 0.035(3) 0.040(4) 0.005(3) 0.013(3) -0.001(3) C13 0.042(4) 0.041(4) 0.054(5) 0.007(3) 0.026(4) 0.006(3) C14 0.052(5) 0.042(4) 0.047(5) -0.002(3) 0.026(4) 0.001(3) C15 0.038(4) 0.053(4) 0.073(6) -0.015(4) 0.024(4) -0.006(3) C16 0.048(5) 0.055(4) 0.054(5) -0.002(3) 0.008(4) -0.001(3) C17 0.065(5) 0.058(5) 0.036(5) 0.015(3) 0.013(4) 0.014(4) C18 0.150(10) 0.103(8) 0.213(13) -0.080(8) 0.157(10) -0.077(7) C19 0.182(13) 0.131(10) 0.194(15) 0.027(9) 0.127(12) 0.028(9) C20 0.262(15) 0.063(6) 0.151(11) 0.036(6) 0.164(11) 0.045(7) _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 O2 1.888(4) . ? Co1 O1 1.908(4) . ? Co1 N2 1.952(6) . ? Co1 N1 1.992(4) . ? N1 C7 1.277(6) . ? N1 C8 1.432(6) . ? N2 C17 1.281(7) . ? N2 C18 1.555(12) . ? O1 C2 1.275(6) . ? O2 C12 1.298(6) . ? Br1 C3 1.888(5) . ? Br2 C13 1.871(6) . ? Cl1 C5 1.718(6) . ? Cl2 C15 1.733(7) . ? C1 C6 1.384(7) . ? C1 C2 1.437(7) . ? C1 C7 1.450(7) . ? C2 C3 1.415(8) . ? C3 C4 1.360(7) . ? C4 C5 1.399(7) . ? C4 H4 0.9300 . ? C5 C6 1.377(7) . ? C6 H6 0.9300 . ? C7 H7 0.9300 . ? C8 C9 1.459(8) . ? C8 C10 1.505(9) . ? C8 H8 0.9800 . ? C9 C10 1.463(10) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 C12 1.390(8) . ? C11 C16 1.401(8) . ? C11 C17 1.450(8) . ? C12 C13 1.409(7) . ? C13 C14 1.369(8) . ? C14 C15 1.372(9) . ? C14 H14 0.9300 . ? C15 C16 1.364(8) . ? C16 H16 0.9300 . ? C17 H17 0.9300 . ? C18 C19 1.299(12) . ? C18 C20 1.358(10) . ? C18 H18 0.9800 . ? C19 C20 1.445(13) . ? C19 H19A 0.9700 . ? C19 H19B 0.9700 . ? C20 H20A 0.9700 . ? C20 H20B 0.9700 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O2 Co1 O1 116.97(17) . . ? O2 Co1 N2 96.0(2) . . ? O1 Co1 N2 115.46(18) . . ? O2 Co1 N1 121.65(17) . . ? O1 Co1 N1 95.27(18) . . ? N2 Co1 N1 112.94(19) . . ? C7 N1 C8 116.1(5) . . ? C7 N1 Co1 121.0(4) . . ? C8 N1 Co1 122.8(4) . . ? C17 N2 C18 110.2(7) . . ? C17 N2 Co1 121.6(4) . . ? C18 N2 Co1 128.2(5) . . ? C2 O1 Co1 125.7(3) . . ? C12 O2 Co1 126.7(4) . . ? C6 C1 C2 121.6(5) . . ? C6 C1 C7 116.1(5) . . ? C2 C1 C7 122.2(5) . . ? O1 C2 C3 120.5(5) . . ? O1 C2 C1 125.7(5) . . ? C3 C2 C1 113.9(5) . . ? C4 C3 C2 124.8(5) . . ? C4 C3 Br1 117.2(4) . . ? C2 C3 Br1 118.0(4) . . ? C3 C4 C5 118.8(5) . . ? C3 C4 H4 120.6 . . ? C5 C4 H4 120.6 . . ? C6 C5 C4 119.9(5) . . ? C6 C5 Cl1 120.7(4) . . ? C4 C5 Cl1 119.3(4) . . ? C5 C6 C1 120.8(5) . . ? C5 C6 H6 119.6 . . ? C1 C6 H6 119.6 . . ? N1 C7 C1 127.9(5) . . ? N1 C7 H7 116.0 . . ? C1 C7 H7 116.0 . . ? N1 C8 C9 120.1(5) . . ? N1 C8 C10 118.7(6) . . ? C9 C8 C10 59.1(4) . . ? N1 C8 H8 115.7 . . ? C9 C8 H8 115.7 . . ? C10 C8 H8 115.7 . . ? C8 C9 C10 62.0(5) . . ? C8 C9 H9A 117.6 . . ? C10 C9 H9A 117.6 . . ? C8 C9 H9B 117.6 . . ? C10 C9 H9B 117.6 . . ? H9A C9 H9B 114.7 . . ? C9 C10 C8 58.9(5) . . ? C9 C10 H10A 117.9 . . ? C8 C10 H10A 117.9 . . ? C9 C10 H10B 117.9 . . ? C8 C10 H10B 117.9 . . ? H10A C10 H10B 115.0 . . ? C12 C11 C16 119.8(6) . . ? C12 C11 C17 124.2(6) . . ? C16 C11 C17 116.0(7) . . ? O2 C12 C11 123.8(5) . . ? O2 C12 C13 119.6(6) . . ? C11 C12 C13 116.6(6) . . ? C14 C13 C12 123.5(6) . . ? C14 C13 Br2 118.1(5) . . ? C12 C13 Br2 118.4(5) . . ? C13 C14 C15 118.2(6) . . ? C13 C14 H14 120.9 . . ? C15 C14 H14 120.9 . . ? C16 C15 C14 120.7(6) . . ? C16 C15 Cl2 120.3(6) . . ? C14 C15 Cl2 119.0(5) . . ? C15 C16 C11 121.1(7) . . ? C15 C16 H16 119.5 . . ? C11 C16 H16 119.5 . . ? N2 C17 C11 127.3(7) . . ? N2 C17 H17 116.4 . . ? C11 C17 H17 116.4 . . ? C19 C18 C20 65.9(7) . . ? C19 C18 N2 112.8(11) . . ? C20 C18 N2 115.0(9) . . ? C19 C18 H18 117.6 . . ? C20 C18 H18 117.6 . . ? N2 C18 H18 117.6 . . ? C18 C19 C20 59.0(7) . . ? C18 C19 H19A 117.9 . . ? C20 C19 H19A 117.9 . . ? C18 C19 H19B 117.9 . . ? C20 C19 H19B 117.9 . . ? H19A C19 H19B 115.0 . . ? C18 C20 C19 55.1(5) . . ? C18 C20 H20A 118.2 . . ? C19 C20 H20A 118.2 . . ? C18 C20 H20B 118.2 . . ? C19 C20 H20B 118.2 . . ? H20A C20 H20B 115.5 . . ? _diffrn_measured_fraction_theta_max 0.984 _diffrn_reflns_theta_full 25.13 _diffrn_measured_fraction_theta_full 0.784 _refine_diff_density_max 0.604 _refine_diff_density_min -0.542 _refine_diff_density_rms 0.062