# Copyright The Royal Society of Chemistry, 1999 # CCDC Number: 186/1501 data_cu _chemical_compound_source 'Synthesized in the laboratory' _chemical_name_systematic ? _chemical_name_common ? _chemical_formula_analytical 'C26 H24 N4 O4 Cl2 Cu' _chemical_formula_moiety '((C26 H22 N4 O3 Cl2(2-) Cu(2+))(2H O)' _chemical_formula_structural '[(C13 H10 N2 O Cl)(C13 H10 N2 O Cl) Cu(2H O)](2H O)' _chemical_formula_sum 'C26 H24 N4 O4 Cl2 Cu' _chemical_formula_weight 590.5 _chemical_melting_point 'Decomposed above 280 degree celcius' _computing_data_collection 'CAD4mach- PC Version ' _computing_cell_refinement ? _computing_data_reduction xtal_DIFDAT_SORTRF_ADDREF_ABSORB _computing_structure_solution xtal_SIMPEL _computing_structure_refinement xtal_CRYLSQ _computing_molecular_graphics xtal _computing_publication_material xtal_BONDLA_CIFIO _cell_length_a 21.139(7) _cell_length_b 15.858(6) _cell_length_c 15.665(6) _cell_angle_alpha 90.00(3) _cell_angle_beta 90.00(3) _cell_angle_gamma 90.00(3) _cell_volume 5251.26(3) _cell_formula_units_Z 8 _cell_measurement_temperature 293 _cell_measurement_reflns_used 25 _cell_measurement_theta_min 8.98 _cell_measurement_theta_max 23.86 _cell_special_details ; ? ; _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M Pbca _symmetry_space_group_name_Hall -P_2ac_2ab loop_ _symmetry_equiv_pos_as_xyz +x,+y,+z 1/2-x,-y,1/2+z 1/2+x,1/2-y,-z -x,1/2+y,1/2-z -x,-y,-z 1/2+x,+y,1/2-z 1/2-x,1/2+y,+z +x,1/2-y,1/2+z _exptl_crystal_description 'Rectangular parallelopiped ' _exptl_crystal_preparation 'Slow evaporation of methanol/water(1:1) solution of the complex' _exptl_crystal_colour Green _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.1 _exptl_crystal_density_diffrn 1.495 _exptl_crystal_density_meas 1.510 _exptl_crystal_density_method Flotation _exptl_crystal_F_000 2423.53 _exptl_absorpt_process_details ? _exptl_absorpt_coefficient_mu 1.08/mm _exptl_absorpt_correction_type analytical _exptl_absorpt_correction_T_min 0.7400 _exptl_absorpt_correction_T_max 0.7417 _exptl_special_details ; ? ; _diffrn_special_details ; ? ; _diffrn_ambient_temperature 293 _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type 'Mo K-alpha ' _diffrn_radiation_source 'Sealed xray_tube ' _diffrn_radiation_monochromator Graphite _diffrn_radiation_detector 'proportional counter ' _diffrn_measurement_device 'CAD4 Mach ' _diffrn_measurement_method theta-2theta _diffrn_standards_number three _diffrn_standards_interval_time 'every hour ' _diffrn_standards_decay_% 0.46% loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l ? ? ? _diffrn_reflns_number 9967 _diffrn_reflns_av_R_equivalents .032 _diffrn_reflns_av_sigmaI/netI .038 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 1.93 _diffrn_reflns_theta_max 25.24 _diffrn_reflns_reduction_process No_monochr_Lp_applied loop_ _atom_type_symbol _atom_type_description _atom_type_oxidation_number _atom_type_number_in_cell _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source c ? 0 208 .002 .002 Int._Tables_Vol_IV_Tables_2.2B_and_2.3.1 h ? 0 192 0 0 Int._Tables_Vol_IV_Tables_2.2B_and_2.3.1 n ? 0 32 .004 .003 Int._Tables_Vol_IV_Tables_2.2B_and_2.3.1 o ? 0 32 .008 .006 Int._Tables_Vol_IV_Tables_2.2B_and_2.3.1 Cl ? 0 16 .132 .159 Int._Tables_Vol_IV_Tables_2.2B_and_2.3.1 Cu ? 0 8 .263 1.266 Int._Tables_Vol_IV_Tables_2.2B_and_2.3.1 loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_thermal_displace_type _atom_site_calc_flag _atom_site_calc_attached_atom Cu .62702(3) .70525(5) .32413(4) .0386(4) Uani ? ? N1 .6646(2) .6166(3) .2496(3) .037(3) Uani ? ? N2 .5460(2) .6546(3) .2787(3) .037(3) Uani ? ? N3 .5882(2) .7905(3) .4017(3) .035(3) Uani ? ? N4 .6835(2) .6863(3) .4238(3) .034(3) Uani ? ? O1w .6623(2) .8076(3) .2350(3) .055(3) Uani ? ? O1 .5123(2) .5266(3) .2219(3) .053(3) Uani ? ? O2 .6903(2) .7182(3) .5655(2) .055(3) Uani ? ? Cl1 .4815(7) .7796(8) .1669(7) .071(4) Uani ? ? Cl11 .5039(4) .5911(5) .4435(5) .086(6) Uani ? ? Cl2 .6599(3) .4982(3) .4376(4) .076(3) Uani ? ? Cl21 .8047(6) .7729(8) .4184(7) .074(6) Uani ? ? C1 .7247(3) .6063(4) .2287(4) .049(2) Uiso ? ? C2 .7459(3) .5373(4) .1826(4) .061(2) Uiso ? ? C3 .7028(3) .4774(4) .1580(5) .062(2) Uiso ? ? C4 .6399(3) .4876(4) .1790(4) .054(2) Uiso ? ? C5 .6211(3) .5588(4) .2233(4) .038(1) Uiso ? ? C6 .5538(3) .5793(4) .2431(4) .036(2) Uiso ? ? C7 .4840(3) .6789(4) .3024(4) .040(2) Uiso ? ? C8 .4491(3) .7380(4) .2572(4) .043(2) Uiso ? ? C9 .3903(3) .7647(4) .2822(5) .058(2) Uiso ? ? C10 .3646(4) .7326(5) .3575(5) .069(2) Uiso ? ? C11 .3981(4) .6770(5) .4043(5) .069(2) Uiso ? ? C12 .4574(4) .6491(4) .3786(5) .061(2) Uiso ? ? C14 .5412(3) .8449(4) .3858(4) .042(2) Uiso ? ? C15 .5116(3) .8904(4) .4488(4) .045(2) Uiso ? ? C16 .5325(3) .8814(4) .5296(4) .048(2) Uiso ? ? C17 .5829(3) .8283(4) .5466(4) .044(2) Uiso ? ? C18 .6101(3) .7833(3) .4816(4) .035(1) Uiso ? ? C19 .6656(3) .7253(4) .4944(4) .040(2) Uiso ? ? C20 .7374(3) .6344(4) .4284(4) .037(2) Uiso ? ? C21 .7977(3) .6712(4) .4210(4) .046(2) Uiso ? ? C22 .8508(3) .6200(5) .4197(5) .069(2) Uiso ? ? C23 .8443(4) .5331(5) .4259(5) .082(3) Uiso ? ? C24 .7867(4) .4956(5) .4316(5) .073(2) Uiso ? ? C25 .7327(3) .5459(4) .4342(4) .054(2) Uiso ? ? O2w .6014(3) .9667(3) .2229(5) .129(6) Uani ? ? C131 .476(3) .781(3) .180(3) .036(9) Uiso ? ? C132 .488(1) .571(1) .426(2) .036(5) Uiso ? ? C261 .661(2) .508(3) .470(2) .05(1) Uiso ? ? C262 .798(1) .782(1) .396(1) .038(5) Uiso ? ? H1 .75579 .64867 .24756 .10000 Uiso ? ? H2 .79074 .53237 .16482 .10000 Uiso ? ? H3 .71704 .42733 .12616 .10000 Uiso ? ? H4 .60798 .44507 .16146 .10000 Uiso ? ? H9 .36587 .80539 .24863 .10000 Uiso ? ? H10 .32312 .75045 .37781 .10000 Uiso ? ? H11 .37902 .65426 .45682 .10000 Uiso ? ? H14 .52764 .85215 .32690 .10000 Uiso ? ? H15 .47767 .92963 .43501 .10000 Uiso ? ? H16 .51114 .91048 .57602 .10000 Uiso ? ? H17 .60021 .82337 .60454 .10000 Uiso ? ? H22 .89290 .64650 .41599 .10000 Uiso ? ? H23 .88279 .49744 .42298 .10000 Uiso ? ? H24 .78261 .43357 .43451 .10000 Uiso ? ? loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 Cu .0402(4) .0468(4) .0287(4) .0029(4) -.0017(4) -.0069(4) N1 .034(3) .055(3) .023(3) .005(3) .002(2) -.005(2) N2 .036(3) .039(3) .037(3) -.002(2) -.002(3) -.002(3) N3 .036(3) .037(3) .032(3) .001(3) -.001(2) -.002(3) N4 .033(3) .040(3) .028(3) .005(2) -.002(2) -.004(2) O1w .079(3) .052(3) .035(3) -.011(3) .014(3) .006(2) O1 .050(3) .055(3) .054(3) -.014(2) .002(3) -.009(2) O2 .065(3) .081(3) .020(2) .016(3) -.008(2) -.003(2) Cl1 .077(5) .094(4) .041(4) .015(3) .005(3) .017(3) Cl11 .098(6) .089(6) .070(5) .011(5) .013(5) .039(4) Cl2 .077(3) .052(3) .099(5) -.011(2) .007(4) .018(3) Cl21 .067(5) .089(7) .066(6) -.012(4) -.020(5) .003(5) O2w .088(5) .097(5) .203(7) .034(4) .062(5) .069(5) _atom_sites_solution_primary 'Cu,N atoms' _atom_sites_solution_secondary 'Rest non hydrogen atoms' _atom_sites_solution_hydrogens 'Positions calculated' _refine_special_details sfls:_F____sigma_weight______full_matrix _refine_ls_structure_factor_coef F _refine_ls_matrix_type full _refine_ls_weighting_scheme sigma _refine_ls_hydrogen_treatment no _refine_ls_extinction_method none _refine_ls_extinction_coef .00000 _refine_ls_extinction_expression ? _refine_ls_abs_structure_details none _refine_ls_abs_structure_Flack 0 _refine_ls_number_reflns 2771 _refine_ls_number_parameters 230 _refine_ls_number_restraints 0 _refine_ls_number_constraints 0 _refine_ls_R_factor_all .097 _refine_ls_R_factor_obs .056 _refine_ls_wR_factor_all .06 _refine_ls_wR_factor_obs .054 _refine_ls_goodness_of_fit_all 2.569 _refine_ls_goodness_of_fit_obs 3.023 _refine_ls_shift/esd_max 0.2873x10-3 _refine_ls_shift/esd_mean 0.3081x10-4 _refine_diff_density_min -.685 _refine_diff_density_max .824 _geom_special_details ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu O1w 2.266(4) . . ? O1w O2w 2.839(7) . . ? C25 C262 4.03(2) . . ? C21 C262 1.80(2) . . ? Cu N1 1.993(5) . . ? Cu N2 2.022(5) . . ? Cu N3 1.994(5) . . ? Cu N4 1.989(5) . . ? N1 C1 1.322(8) . . ? N1 C5 1.362(8) . . ? N2 C6 1.327(8) . . ? N2 C7 1.414(8) . . ? N3 C14 1.339(8) . . ? N3 C18 1.340(7) . . ? N4 C19 1.324(8) . . ? N4 C20 1.406(7) . . ? O1 C6 1.256(7) . . ? O2 C19 1.235(7) . . ? Cl1 C8 1.70(1) . . ? Cl1 C131 .23(5) . . ? Cl11 C12 1.69(1) . . ? Cl11 C132 .53(2) . . ? Cl2 C25 1.715(9) . . ? Cl2 C261 .53(3) . . ? Cl21 C21 1.62(1) . . ? Cl21 C262 .40(2) . . ? C1 C2 1.39(1) . . ? C1 H1 .985(7) . . ? C2 C3 1.37(1) . . ? C2 H2 .992(7) . . ? C3 C4 1.38(1) . . ? C3 H3 .985(7) . . ? C4 C5 1.384(9) . . ? C4 H4 .992(6) . . ? C5 C6 1.492(9) . . ? C7 C8 1.388(9) . . ? C7 C12 1.40(1) . . ? C8 C9 1.369(9) . . ? C8 C131 1.50(5) . . ? C9 C10 1.39(1) . . ? C9 H9 .980(7) . . ? C10 C11 1.35(1) . . ? C10 H10 .976(8) . . ? C11 C12 1.39(1) . . ? C11 H11 .985(8) . . ? C12 C132 1.58(2) . . ? C14 C15 1.373(9) . . ? C14 H14 .973(6) . . ? C15 C16 1.348(9) . . ? C15 H15 .974(6) . . ? C16 C17 1.384(9) . . ? C16 H16 .973(6) . . ? C17 C18 1.370(8) . . ? C17 H17 .981(6) . . ? C18 C19 1.504(8) . . ? C20 C21 1.407(9) . . ? C20 C25 1.409(9) . . ? C21 C22 1.39(1) . . ? C22 C23 1.39(1) . . ? C22 H22 .986(7) . . ? C23 C24 1.36(1) . . ? C23 H23 .992(8) . . ? C24 C25 1.39(1) . . ? C24 H24 .989(8) . . ? C25 C261 1.72(4) . . ? loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 _geom_contact_publ_flag ? ? ? ? ? ? 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 Cu O1w 90.8(2) . . . ? N2 Cu O1w 110.3(2) . . . ? N3 Cu O1w 91.4(2) . . . ? N4 Cu O1w 113.2(2) . . . ? N1 Cu N2 81.5(2) . . . ? N1 Cu N3 177.8(2) . . . ? N1 Cu N4 96.5(2) . . . ? N2 Cu N3 97.8(2) . . . ? N2 Cu N4 136.5(2) . . . ? N3 Cu N4 82.6(2) . . . ? Cu N1 C1 128.0(4) . . . ? Cu N1 C5 112.4(4) . . . ? C1 N1 C5 119.5(5) . . . ? Cu N2 C6 113.6(4) . . . ? Cu N2 C7 125.7(4) . . . ? C6 N2 C7 118.0(5) . . . ? Cu N3 C14 129.0(4) . . . ? Cu N3 C18 111.7(4) . . . ? C14 N3 C18 119.0(5) . . . ? Cu N4 C19 114.4(4) . . . ? Cu N4 C20 127.9(4) . . . ? C19 N4 C20 117.6(5) . . . ? C8 Cl1 C131 27(12) . . . ? C12 Cl11 C132 70(3) . . . ? C25 Cl2 C261 82(5) . . . ? C21 Cl21 C262 110(4) . . . ? N1 C1 C2 122.4(6) . . . ? N1 C1 H1 118.8(6) . . . ? C2 C1 H1 118.7(6) . . . ? C1 C2 C3 118.7(7) . . . ? C1 C2 H2 121.1(7) . . . ? C3 C2 H2 120.1(7) . . . ? C2 C3 C4 119.5(6) . . . ? C2 C3 H3 119.9(7) . . . ? C4 C3 H3 120.6(7) . . . ? C3 C4 C5 119.4(6) . . . ? C3 C4 H4 120.6(6) . . . ? C5 C4 H4 119.9(6) . . . ? N1 C5 C4 120.4(6) . . . ? N1 C5 C6 115.8(5) . . . ? C4 C5 C6 123.7(5) . . . ? N2 C6 O1 128.6(6) . . . ? N2 C6 C5 113.7(5) . . . ? O1 C6 C5 117.7(5) . . . ? N2 C7 C8 122.9(5) . . . ? N2 C7 C12 120.2(6) . . . ? C8 C7 C12 116.6(6) . . . ? Cl1 C8 C7 118.0(7) . . . ? Cl1 C8 C9 118.9(7) . . . ? Cl1 C8 C131 4(2) . . . ? C7 C8 C9 123.1(6) . . . ? C7 C8 C131 121(2) . . . ? C9 C8 C131 116(2) . . . ? C8 C9 C10 118.8(6) . . . ? C8 C9 H9 121.9(7) . . . ? C10 C9 H9 119.3(7) . . . ? C9 C10 C11 119.6(7) . . . ? C9 C10 H10 121.4(7) . . . ? C11 C10 H10 119.0(8) . . . ? C10 C11 C12 121.7(7) . . . ? C10 C11 H11 118.6(7) . . . ? C12 C11 H11 119.7(7) . . . ? Cl11 C12 C7 117.6(6) . . . ? Cl11 C12 C11 121.6(6) . . . ? Cl11 C12 C132 18.4(9) . . . ? C7 C12 C11 120.1(7) . . . ? C7 C12 C132 120(1) . . . ? C11 C12 C132 119(1) . . . ? N3 C14 C15 122.9(6) . . . ? N3 C14 H14 118.1(6) . . . ? C15 C14 H14 119.1(6) . . . ? C14 C15 C16 118.0(6) . . . ? C14 C15 H15 120.7(6) . . . ? C16 C15 H15 121.2(6) . . . ? C15 C16 C17 119.9(6) . . . ? C15 C16 H16 119.9(6) . . . ? C17 C16 H16 120.2(6) . . . ? C16 C17 C18 119.8(6) . . . ? C16 C17 H17 120.9(6) . . . ? C18 C17 H17 119.3(6) . . . ? N3 C18 C17 120.4(5) . . . ? N3 C18 C19 116.5(5) . . . ? C17 C18 C19 123.1(5) . . . ? N4 C19 O2 126.1(6) . . . ? N4 C19 C18 113.5(5) . . . ? O2 C19 C18 120.4(5) . . . ? N4 C20 C21 119.1(5) . . . ? N4 C20 C25 121.9(5) . . . ? C21 C20 C25 118.9(5) . . . ? Cl21 C21 C20 120.0(6) . . . ? Cl21 C21 C22 120.6(7) . . . ? C20 C21 C22 119.4(6) . . . ? C21 C22 C23 120.1(7) . . . ? C21 C22 H22 118.9(7) . . . ? C23 C22 H22 121.0(7) . . . ? C22 C23 C24 121.8(7) . . . ? C22 C23 H23 118.8(8) . . . ? C24 C23 H23 119.3(8) . . . ? C23 C24 C25 119.1(7) . . . ? C23 C24 H24 121.2(8) . . . ? C25 C24 H24 119.7(7) . . . ? Cl2 C25 C20 120.3(5) . . . ? Cl2 C25 C24 118.9(6) . . . ? Cl2 C25 C261 18(1) . . . ? C20 C25 C24 120.6(6) . . . ? C20 C25 C261 116(1) . . . ? C24 C25 C261 122(1) . . . ? Cl1 C131 C8 148(14) . . . ? Cl11 C132 C12 92(3) . . . ? Cl2 C261 C25 80(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 N2 Cu N1 C1 170.8(5) . . . . ? N2 Cu N1 C5 -13.3(4) . . . . ? N3 Cu N1 C1 -120(5) . . . . ? N3 Cu N1 C5 56(5) . . . . ? N4 Cu N1 C1 -53.0(5) . . . . ? N4 Cu N1 C5 122.9(4) . . . . ? N1 Cu N2 C6 16.2(4) . . . . ? N1 Cu N2 C7 177.2(5) . . . . ? N3 Cu N2 C6 -161.7(4) . . . . ? N3 Cu N2 C7 -.7(5) . . . . ? N4 Cu N2 C6 -74.2(5) . . . . ? N4 Cu N2 C7 86.7(5) . . . . ? N1 Cu N3 C14 -116(5) . . . . ? N1 Cu N3 C18 57(5) . . . . ? N2 Cu N3 C14 -47.2(5) . . . . ? N2 Cu N3 C18 125.8(4) . . . . ? N4 Cu N3 C14 176.7(5) . . . . ? N4 Cu N3 C18 -10.3(4) . . . . ? N1 Cu N4 C19 -168.7(4) . . . . ? N1 Cu N4 C20 8.2(5) . . . . ? N2 Cu N4 C19 -84.3(5) . . . . ? N2 Cu N4 C20 92.7(5) . . . . ? N3 Cu N4 C19 9.2(4) . . . . ? N3 Cu N4 C20 -173.8(5) . . . . ? Cu N1 C1 C2 173.8(5) . . . . ? Cu N1 C1 H1 -4.9(9) . . . . ? C5 N1 C1 C2 -1.9(9) . . . . ? C5 N1 C1 H1 179.4(6) . . . . ? Cu N1 C5 C4 -172.8(5) . . . . ? Cu N1 C5 C6 8.9(6) . . . . ? C1 N1 C5 C4 3.5(9) . . . . ? C1 N1 C5 C6 -174.8(5) . . . . ? Cu N2 C6 O1 167.5(5) . . . . ? Cu N2 C6 C5 -15.5(6) . . . . ? C7 N2 C6 O1 4.9(9) . . . . ? C7 N2 C6 C5 -178.1(5) . . . . ? Cu N2 C7 C8 93.8(7) . . . . ? Cu N2 C7 C12 -80.2(7) . . . . ? C6 N2 C7 C8 -106.0(7) . . . . ? C6 N2 C7 C12 80.0(8) . . . . ? Cu N3 C14 C15 168.6(5) . . . . ? Cu N3 C14 H14 -11.4(9) . . . . ? C18 N3 C14 C15 -4.0(9) . . . . ? C18 N3 C14 H14 176.0(5) . . . . ? Cu N3 C18 C17 -171.0(4) . . . . ? Cu N3 C18 C19 9.9(6) . . . . ? C14 N3 C18 C17 2.8(8) . . . . ? C14 N3 C18 C19 -176.3(5) . . . . ? Cu N4 C19 O2 174.4(5) . . . . ? Cu N4 C19 C18 -6.3(6) . . . . ? C20 N4 C19 O2 -2.9(9) . . . . ? C20 N4 C19 C18 176.4(5) . . . . ? Cu N4 C20 C21 99.9(6) . . . . ? Cu N4 C20 C25 -75.7(7) . . . . ? C19 N4 C20 C21 -83.2(7) . . . . ? C19 N4 C20 C25 101.2(7) . . . . ? C131 Cl1 C8 C7 -130(28) . . . . ? C131 Cl1 C8 C9 49(28) . . . . ? C131 Cl1 C8 C131 0(39) . . . . ? C8 Cl1 C131 C8 -.0(6) . . . . ? C132 Cl11 C12 C7 -103(3) . . . . ? C132 Cl11 C12 C11 86(3) . . . . ? C132 Cl11 C12 C132 0(4) . . . . ? C12 Cl11 C132 C12 .0(4) . . . . ? C261 Cl2 C25 C20 -79(5) . . . . ? C261 Cl2 C25 C24 105(5) . . . . ? C261 Cl2 C25 C261 0(6) . . . . ? C25 Cl2 C261 C25 .0(3) . . . . ? C262 Cl21 C21 C20 -72(4) . . . . ? C262 Cl21 C21 C22 111(4) . . . . ? N1 C1 C2 C3 0(1) . . . . ? N1 C1 C2 H2 176.6(6) . . . . ? H1 C1 C2 C3 178.6(6) . . . . ? H1 C1 C2 H2 -5(1) . . . . ? C1 C2 C3 C4 0(1) . . . . ? C1 C2 C3 H3 -178.8(7) . . . . ? H2 C2 C3 C4 -176.3(7) . . . . ? H2 C2 C3 H3 4(1) . . . . ? C2 C3 C4 C5 1(1) . . . . ? C2 C3 C4 H4 179.6(7) . . . . ? H3 C3 C4 C5 -179.5(6) . . . . ? H3 C3 C4 H4 -1(1) . . . . ? C3 C4 C5 N1 -3(1) . . . . ? C3 C4 C5 C6 175.0(6) . . . . ? H4 C4 C5 N1 178.3(6) . . . . ? H4 C4 C5 C6 -3(1) . . . . ? N1 C5 C6 N2 4.5(8) . . . . ? N1 C5 C6 O1 -178.2(5) . . . . ? C4 C5 C6 N2 -173.8(6) . . . . ? C4 C5 C6 O1 3.6(9) . . . . ? N2 C7 C8 Cl1 3(1) . . . . ? N2 C7 C8 C9 -176.7(6) . . . . ? N2 C7 C8 C131 -1(2) . . . . ? C12 C7 C8 Cl1 176.9(7) . . . . ? C12 C7 C8 C9 -2.5(9) . . . . ? C12 C7 C8 C131 173(2) . . . . ? N2 C7 C12 Cl11 5.1(9) . . . . ? N2 C7 C12 C11 176.1(6) . . . . ? N2 C7 C12 C132 -16(1) . . . . ? C8 C7 C12 Cl11 -169.2(6) . . . . ? C8 C7 C12 C11 2(1) . . . . ? C8 C7 C12 C132 170(1) . . . . ? Cl1 C8 C9 C10 -178.0(7) . . . . ? Cl1 C8 C9 H9 2(1) . . . . ? C7 C8 C9 C10 1(1) . . . . ? C7 C8 C9 H9 -178.3(6) . . . . ? C131 C8 C9 C10 -175(2) . . . . ? C131 C8 C9 H9 6(2) . . . . ? Cl1 C8 C131 Cl1 0(9) . . . . ? C7 C8 C131 Cl1 52(29) . . . . ? C9 C8 C131 Cl1 -132(28) . . . . ? C8 C9 C10 C11 0(1) . . . . ? C8 C9 C10 H10 179.4(7) . . . . ? H9 C9 C10 C11 -179.6(7) . . . . ? H9 C9 C10 H10 0(1) . . . . ? C9 C10 C11 C12 -1(1) . . . . ? C9 C10 C11 H11 -179.0(7) . . . . ? H10 C10 C11 C12 179.8(7) . . . . ? H10 C10 C11 H11 2(1) . . . . ? C10 C11 C12 Cl11 170.8(7) . . . . ? C10 C11 C12 C7 0(1) . . . . ? C10 C11 C12 C132 -168(1) . . . . ? H11 C11 C12 Cl11 -12(1) . . . . ? H11 C11 C12 C7 177.8(7) . . . . ? H11 C11 C12 C132 9(1) . . . . ? Cl11 C12 C132 Cl11 0(1) . . . . ? C7 C12 C132 Cl11 87(3) . . . . ? C11 C12 C132 Cl11 -104(3) . . . . ? N3 C14 C15 C16 2.1(9) . . . . ? N3 C14 C15 H15 179.7(6) . . . . ? H14 C14 C15 C16 -177.9(6) . . . . ? H14 C14 C15 H15 0(1) . . . . ? C14 C15 C16 C17 .8(9) . . . . ? C14 C15 C16 H16 -176.8(6) . . . . ? H15 C15 C16 C17 -176.8(6) . . . . ? H15 C15 C16 H16 6(1) . . . . ? C15 C16 C17 C18 -1.9(9) . . . . ? C15 C16 C17 H17 176.6(6) . . . . ? H16 C16 C17 C18 175.7(6) . . . . ? H16 C16 C17 H17 -6(1) . . . . ? C16 C17 C18 N3 -.0(9) . . . . ? C16 C17 C18 C19 179.1(6) . . . . ? H17 C17 C18 N3 -178.5(5) . . . . ? H17 C17 C18 C19 .5(9) . . . . ? N3 C18 C19 N4 -2.6(7) . . . . ? N3 C18 C19 O2 176.7(5) . . . . ? C17 C18 C19 N4 178.3(5) . . . . ? C17 C18 C19 O2 -2.3(9) . . . . ? N4 C20 C21 Cl21 7.0(9) . . . . ? N4 C20 C21 C22 -175.7(6) . . . . ? C25 C20 C21 Cl21 -177.3(7) . . . . ? C25 C20 C21 C22 .1(9) . . . . ? N4 C20 C25 Cl2 -.9(9) . . . . ? N4 C20 C25 C24 174.7(6) . . . . ? N4 C20 C25 C261 -20(1) . . . . ? C21 C20 C25 Cl2 -176.5(5) . . . . ? C21 C20 C25 C24 0(1) . . . . ? C21 C20 C25 C261 164(1) . . . . ? Cl21 C21 C22 C23 177.0(7) . . . . ? Cl21 C21 C22 H22 -1(1) . . . . ? C20 C21 C22 C23 0(1) . . . . ? C20 C21 C22 H22 -178.5(7) . . . . ? C21 C22 C23 C24 2(1) . . . . ? C21 C22 C23 H23 178.1(7) . . . . ? H22 C22 C23 C24 179.6(8) . . . . ? H22 C22 C23 H23 -4(1) . . . . ? C22 C23 C24 C25 -2(1) . . . . ? C22 C23 C24 H24 178.4(8) . . . . ? H23 C23 C24 C25 -178.9(8) . . . . ? H23 C23 C24 H24 2(1) . . . . ? C23 C24 C25 Cl2 177.7(7) . . . . ? C23 C24 C25 C20 2(1) . . . . ? C23 C24 C25 C261 -162(1) . . . . ? H24 C24 C25 Cl2 -3(1) . . . . ? H24 C24 C25 C20 -178.7(7) . . . . ? H24 C24 C25 C261 17(2) . . . . ? Cl2 C25 C261 Cl2 -.0(8) . . . . ? C20 C25 C261 Cl2 110(4) . . . . ? C24 C25 C261 Cl2 -85(4) . . . . ? _reflns_limit_h_min 0 _reflns_limit_h_max 25 _reflns_limit_k_min -18 _reflns_limit_k_max 0 _reflns_limit_l_min 0 _reflns_limit_l_max 18 _reflns_number_total 4618 _reflns_number_observed 2779 _reflns_observed_criterion ' refl_observed_if_Inet_>_.000_sigma(Inet)' _reflns_d_resolution_high .833 _reflns_d_resolution_low 10.57 loop_ _reflns_scale_group_code _reflns_scale_meas_F ? 4.1465 loop_ _refln_index_h _refln_index_k _refln_index_l _refln_F_meas _refln_F_calc _refln_F_sigma _refln_observed_status _refln_scale_group_code ? ? ? ? ? ? ? ? _publ_requested_journal 'JCS Dalton Transactions' _publ_requested_coeditor_name ? _publ_contact_author ; ? name Prof. R. Mukherjee ? institute Indian Institute of Technology Kanpur ? department Department of Chemistry ? address 208 016 ? city Kanpur ? country India ; _publ_contact_letter ; ? letter to co-editor ; _publ_contact_author_phphone +91-512-597437 _publ_contact_author_faxFax ; +91-512-597436 +91-512-590260 ; _publ_contact_author_email rnm@iitk.ac.in loop_ _publ_author_name _publ_author_address '? surname, initials' ; ? institute ? department ? address ? city ? country ; _publ_section_title ; Synthesis, crystal structure and properties of trigonal bipyramidal [M(L5)2(H2O)].H2O complexes [M = cobalt(II) (S = 3/2) and copper(II) (S = 1/2); HL5 = N-2-chloro-6-methylphenyl-pyridine -2-carboxamide] Geometry Due to Steric Effects. ; _publ_section_abstract ; ? ; _publ_section_comment ; ? ; _publ_section_experimental ; ? ; _publ_section_references ; ? ; _publ_section_figure_captions ; ? ; _publ_section_acknowledgements ; ; #============================================================================== # (IUCr Office Use Only) _journal_date_recd_electronic ? _journal_date_to_coeditor ? _journal_date_from_coeditor ? _journal_date_accepted ? _journal_date_printers_first ? _journal_date_printers_final ? _journal_date_proofs_out ? _journal_date_proofs_in ? _journal_coeditor_name ? _journal_coeditor_code ? _journal_coeditor_notes ; ? ; _journal_techeditor_code ? _journal_techeditor_notes ; ? ; _journal_coden_ASTM ? _journal_name_full ? _journal_year ? _journal_volume ? _journal_issue ? _journal_page_first ? _journal_page_last ? _journal_suppl_publ_number ? _journal_suppl_publ_pages ? data_co _chemical_compound_source 'Synthesized in the laboratory ' _chemical_name_systematic ? _chemical_name_common ? _chemical_formula_analytical 'C26 H24 N4 O4 Cl2 Co' _chemical_formula_moiety '((C26 H22 N4 O3 Cl2 (2-) Co(2+))(H2 O)' _chemical_formula_structural '[(C13 H10 N2 O Cl)(C13 H10 N2 O Cl) Co (H2 O)] (H2 O)' _chemical_formula_sum 'C26 H24 N4 O4 Cl2 Co ' _chemical_formula_weight 585.93 _chemical_melting_point 'decomposed above 280 degree celsius ' _computing_data_collection ' CAD4mach -PC Version ' _computing_cell_refinement ? _computing_data_reduction xtal_DIFDAT_SORTRF_ADDREF_ABSORB _computing_structure_solution xtal_SIMPEL _computing_structure_refinement xtal_CRYLSQ _computing_molecular_graphics xtal _computing_publication_material xtal_BONDLA_CIFIO _cell_length_a 21.039(9) _cell_length_b 15.841(3) _cell_length_c 15.678(5) _cell_angle_alpha 90.00(1) _cell_angle_beta 90.00(3) _cell_angle_gamma 90.00(3) _cell_volume 5225.15(3) _cell_formula_units_Z 8 _cell_measurement_temperature 293 _cell_measurement_reflns_used 25 _cell_measurement_theta_min 10.94 _cell_measurement_theta_max 23.42 _cell_special_details ; ? ; _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M Pbca _symmetry_space_group_name_Hall -P_2ac_2ab loop_ _symmetry_equiv_pos_as_xyz +x,+y,+z 1/2-x,-y,1/2+z 1/2+x,1/2-y,-z -x,1/2+y,1/2-z -x,-y,-z 1/2+x,+y,1/2-z 1/2-x,1/2+y,+z +x,1/2-y,1/2+z _exptl_crystal_description 'rectangular parallelopiped ' _exptl_crystal_preparation 'Slow evaporation of methanol/water(1:1) ' _exptl_crystal_colour Yellow _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.1 _exptl_crystal_density_diffrn 1.491 _exptl_crystal_density_meas 1.510 _exptl_crystal_density_method flotation _exptl_crystal_F_000 2407.55 _exptl_absorpt_process_details ? _exptl_absorpt_coefficient_mu 0.90/mm _exptl_absorpt_correction_type analytical _exptl_absorpt_correction_T_min 0.7378 _exptl_absorpt_correction_T_max 0.7394 _exptl_special_details ; ? ; _diffrn_special_details ; ? ; _diffrn_ambient_temperature 293 _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type 'Mo K-alpha ' _diffrn_radiation_source 'Sealed xray_tube ' _diffrn_radiation_monochromator Graphite _diffrn_radiation_detector 'proportional counter ' _diffrn_measurement_device CAD4mach _diffrn_measurement_method theta-2theta _diffrn_standards_number three _diffrn_standards_interval_time 'every hour ' _diffrn_standards_decay_% 0.86% _diffrn_reflns_number 5243 _diffrn_reflns_av_R_equivalents ? _diffrn_reflns_av_sigmaI/netI .06 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 1.94 _diffrn_reflns_theta_max 24.98 _diffrn_reflns_reduction_process No_monochr_Lp_applied loop_ _atom_type_symbol _atom_type_description _atom_type_oxidation_number _atom_type_number_in_cell _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source c ? 0 208 .002 .002 Int._Tables_Vol_IV_Tables_2.2B_and_2.3.1 h ? 0 192 0 0 Int._Tables_Vol_IV_Tables_2.2B_and_2.3.1 n ? 0 32 .004 .003 Int._Tables_Vol_IV_Tables_2.2B_and_2.3.1 o ? 0 32 .008 .006 Int._Tables_Vol_IV_Tables_2.2B_and_2.3.1 Cl ? 0 16 .132 .159 Int._Tables_Vol_IV_Tables_2.2B_and_2.3.1 Co ? 0 8 .299 .973 Int._Tables_Vol_IV_Tables_2.2B_and_2.3.1 loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_thermal_displace_type _atom_site_calc_flag _atom_site_calc_attached_atom Co .62674(6) .72423(8) .31139(7) .0373(6) Uani ? ? O1w .6517(3) .8127(3) .2231(3) .045(4) Uani ? ? N1 .6638(4) .6246(4) .2366(4) .041(5) Uani ? ? N2 .5464(3) .6594(4) .2880(4) .038(5) Uani ? ? N3 .5859(3) .8096(4) .3984(4) .038(5) Uani ? ? N4 .6772(3) .6964(4) .4164(4) .036(5) Uani ? ? O1 .5108(3) .5295(4) .2391(4) .061(5) Uani ? ? O2 .6835(3) .7215(4) .5614(3) .052(4) Uani ? ? Cl1 .4787(5) .7821(6) .1793(8) .061(4) Uani ? ? Cl11 .5109(9) .603(1) .461(1) .08(1) Uani ? ? Cl2 .6600(8) .5096(9) .441(1) .078(8) Uani ? ? Cl21 .7940(6) .7920(7) .3860(7) .068(6) Uani ? ? C1 .7227(5) .6120(6) .2091(6) .058(3) Uiso ? ? C2 .7415(5) .5370(7) .1692(6) .075(4) Uiso ? ? C3 .6958(5) .4757(7) .1581(6) .071(4) Uiso ? ? C4 .6341(5) .4880(6) .1860(6) .057(3) Uiso ? ? C5 .6190(5) .5642(5) .2256(5) .038(2) Uiso ? ? C6 .5525(4) .5829(6) .2527(6) .040(3) Uiso ? ? C7 .4840(4) .6822(5) .3158(6) .043(2) Uiso ? ? C8 .4479(4) .7405(6) .2696(6) .048(3) Uiso ? ? C9 .3881(4) .7660(6) .2981(6) .059(3) Uiso ? ? C10 .3656(5) .7356(6) .3750(6) .065(3) Uiso ? ? C11 .4012(5) .6810(7) .4217(6) .067(3) Uiso ? ? C12 .4611(5) .6532(6) .3965(7) .062(3) Uiso ? ? C14 .5379(4) .8634(6) .3873(6) .043(3) Uiso ? ? C15 .5051(4) .8994(6) .4541(6) .050(3) Uiso ? ? C16 .5238(4) .8796(6) .5371(6) .048(3) Uiso ? ? C17 .5745(4) .8268(6) .5495(6) .046(3) Uiso ? ? C18 .6042(4) .7924(5) .4793(5) .036(2) Uiso ? ? C19 .6598(4) .7320(6) .4888(6) .039(2) Uiso ? ? C20 .7340(4) .6467(5) .4205(5) .036(2) Uiso ? ? C21 .7914(4) .6849(6) .4075(6) .045(3) Uiso ? ? C22 .8475(5) .6352(7) .4062(7) .068(3) Uiso ? ? C23 .8430(5) .5491(7) .4170(7) .071(4) Uiso ? ? C24 .7860(5) .5112(6) .4279(7) .062(3) Uiso ? ? C25 .7299(5) .5580(6) .4322(6) .049(3) Uiso ? ? O2w .6051(3) .9729(4) .2161(5) .107(7) Uani ? ? C261 .655(3) .515(4) .467(4) .07(2) Uiso ? ? C262 .795(2) .779(3) .408(2) .021(7) Uiso ? ? C131 .467(4) .795(5) .174(6) .03(2) Uiso ? ? C132 .496(1) .580(2) .444(2) .059(9) Uiso ? ? H1 .75541 .65662 .21357 .10000 Uiso ? ? H2 .78524 .52503 .15093 .10000 Uiso ? ? H3 .70874 .42319 .12881 .10000 Uiso ? ? H4 .60258 .44313 .17735 .10000 Uiso ? ? H9 .36115 .80382 .26353 .10000 Uiso ? ? H10 .32373 .75500 .39652 .10000 Uiso ? ? H11 .38301 .66104 .47562 .10000 Uiso ? ? H14 .52477 .87815 .32983 .10000 Uiso ? ? H15 .46956 .93806 .44340 .10000 Uiso ? ? H16 .50066 .90384 .58570 .10000 Uiso ? ? H17 .58844 .81364 .60788 .10000 Uiso ? ? H22 .89008 .66191 .39783 .10000 Uiso ? ? H23 .88279 .51517 .41904 .10000 Uiso ? ? H24 .78413 .44869 .43140 .10000 Uiso ? ? loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 Co .0451(7) .0392(7) .0276(6) -.0039(8) .0005(7) -.0008(8) O1w .065(5) .043(4) .028(4) -.014(3) .004(3) .007(3) N1 .050(5) .053(5) .021(4) .006(5) .006(4) -.001(4) N2 .042(5) .035(4) .036(5) -.002(4) -.002(4) -.000(4) N3 .045(5) .029(4) .040(5) -.003(4) .003(4) .003(4) N4 .040(5) .040(5) .028(5) .001(4) -.003(4) -.005(4) O1 .065(5) .047(4) .070(5) -.014(4) -.001(4) -.014(4) O2 .061(4) .067(5) .027(3) .017(4) -.006(3) -.001(4) Cl1 .064(5) .073(5) .045(3) .015(4) -.005(4) .012(3) Cl11 .12(1) .052(9) .08(1) -.005(9) .00(1) .026(9) Cl2 .074(6) .056(5) .10(1) -.009(4) .015(7) .022(7) Cl21 .074(5) .046(6) .083(8) -.012(4) .011(6) .011(5) O2w .096(7) .072(6) .153(9) .025(5) .049(6) .048(6) _atom_sites_solution_primary 'Co, N atoms' _atom_sites_solution_secondary 'Rest of the non hydrogen atoms' _atom_sites_solution_hydrogens 'Positions calculated' _refine_special_details sfls:_F____sigma_weight______full_matrix _refine_ls_structure_factor_coef F _refine_ls_matrix_type full _refine_ls_weighting_scheme sigma _refine_ls_hydrogen_treatment no _refine_ls_extinction_method none _refine_ls_extinction_coef .00000 _refine_ls_extinction_expression no _refine_ls_abs_structure_details none _refine_ls_abs_structure_Flack 0 _refine_ls_number_reflns 1978 _refine_ls_number_parameters 230 _refine_ls_number_restraints 0 _refine_ls_number_constraints 0 _refine_ls_R_factor_all .149 _refine_ls_R_factor_obs .058 _refine_ls_wR_factor_all .058 _refine_ls_wR_factor_obs .046 _refine_ls_goodness_of_fit_all 1.968 _refine_ls_goodness_of_fit_obs 2.499 _refine_ls_shift/esd_max .3388x10E-3 _refine_ls_shift/esd_mean .2729x10E-4 _refine_diff_density_min -.78 _refine_diff_density_max .698 _geom_special_details ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag Co N1 2.115(7) . . ? Co N2 2.012(7) . . ? Co N3 2.104(7) . . ? Co N4 2.008(7) . . ? Co O1w 2.039(6) . . ? O1w O2w 2.723(9) . . ? N1 C1 1.33(1) . . ? N1 C5 1.35(1) . . ? N2 C6 1.34(1) . . ? N2 C7 1.43(1) . . ? N3 C14 1.33(1) . . ? N3 C18 1.35(1) . . ? N4 C19 1.32(1) . . ? N4 C20 1.43(1) . . ? O1 C6 1.24(1) . . ? O2 C19 1.26(1) . . ? Cl1 C8 1.69(1) . . ? Cl1 C131 .33(8) . . ? Cl11 C12 1.66(2) . . ? Cl11 C132 .56(3) . . ? Cl2 C25 1.66(2) . . ? Cl2 C261 .44(6) . . ? Cl21 C21 1.73(1) . . ? Cl21 C262 .40(4) . . ? C1 C2 1.40(1) . . ? C1 H1 .99(1) . . ? C2 C3 1.38(2) . . ? C2 H2 .98(1) . . ? C3 C4 1.38(1) . . ? C3 H3 .99(1) . . ? C4 C5 1.39(1) . . ? C4 H4 .98(1) . . ? C5 C6 1.49(1) . . ? C7 C8 1.40(1) . . ? C7 C12 1.43(1) . . ? C8 C9 1.39(1) . . ? C9 C10 1.38(1) . . ? C9 H9 .987(9) . . ? C10 C11 1.36(1) . . ? C10 H10 .99(1) . . ? C11 C12 1.39(1) . . ? C11 H11 .98(1) . . ? C12 C132 1.55(3) . . ? C14 C15 1.38(1) . . ? C14 H14 .970(9) . . ? C15 C16 1.39(1) . . ? C15 H15 .981(9) . . ? C16 C17 1.37(1) . . ? C16 H16 .982(9) . . ? C17 C18 1.38(1) . . ? C17 H17 .984(9) . . ? C18 C19 1.52(1) . . ? C20 C21 1.37(1) . . ? C20 C25 1.42(1) . . ? C21 C22 1.42(1) . . ? C21 C262 1.49(4) . . ? C22 C23 1.38(2) . . ? C22 H22 1.00(1) . . ? C23 C24 1.35(2) . . ? C23 H23 .99(1) . . ? C24 C25 1.40(1) . . ? C24 H24 .99(1) . . ? loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 _geom_contact_publ_flag ? ? ? ? ? ? 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 Co N2 80.1(3) . . . ? N1 Co N3 171.7(3) . . . ? N1 Co N4 95.5(3) . . . ? N1 Co O1w 92.4(2) . . . ? N2 Co N3 95.9(3) . . . ? N2 Co N4 118.8(3) . . . ? N2 Co O1w 116.3(3) . . . ? N3 Co N4 80.0(3) . . . ? N3 Co O1w 96.0(2) . . . ? N4 Co O1w 124.9(3) . . . ? C1 N1 C5 120.1(8) . . . ? Co N2 C6 117.1(6) . . . ? Co N2 C7 126.0(5) . . . ? C6 N2 C7 116.3(7) . . . ? C14 N3 C18 117.9(7) . . . ? Co N4 C19 117.7(6) . . . ? Co N4 C20 126.8(5) . . . ? C19 N4 C20 115.3(7) . . . ? C8 Cl1 C131 99(16) . . . ? C12 Cl11 C132 70(3) . . . ? C25 Cl2 C261 101(8) . . . ? C21 Cl21 C262 49(6) . . . ? N1 C1 C2 122.5(9) . . . ? N1 C1 H1 121.2(9) . . . ? C2 C1 H1 116(1) . . . ? C1 C2 C3 117(1) . . . ? C1 C2 H2 124(1) . . . ? C3 C2 H2 119(1) . . . ? C2 C3 C4 121(1) . . . ? C2 C3 H3 117(1) . . . ? C4 C3 H3 122(1) . . . ? C3 C4 C5 118.5(9) . . . ? C3 C4 H4 119.1(9) . . . ? C5 C4 H4 122.4(9) . . . ? N1 C5 C4 120.7(9) . . . ? N1 C5 C6 118.4(8) . . . ? C4 C5 C6 120.8(8) . . . ? N2 C6 O1 128.4(9) . . . ? N2 C6 C5 112.8(8) . . . ? O1 C6 C5 118.7(8) . . . ? N2 C7 C8 120.5(8) . . . ? N2 C7 C12 119.9(8) . . . ? C8 C7 C12 119.2(8) . . . ? Cl1 C8 C7 119.0(8) . . . ? Cl1 C8 C9 119.9(8) . . . ? C7 C8 C9 121.1(8) . . . ? C8 C9 C10 119.1(9) . . . ? C8 C9 H9 121.3(9) . . . ? C10 C9 H9 119.6(9) . . . ? C9 C10 C11 120.2(9) . . . ? C9 C10 H10 119.5(9) . . . ? C11 C10 H10 120.3(9) . . . ? C10 C11 C12 123.2(9) . . . ? C10 C11 H11 117(1) . . . ? C12 C11 H11 120(1) . . . ? Cl11 C12 C7 119(1) . . . ? Cl11 C12 C11 123(1) . . . ? Cl11 C12 C132 20(1) . . . ? C7 C12 C11 117.0(9) . . . ? C7 C12 C132 120(1) . . . ? C11 C12 C132 121(1) . . . ? N3 C14 C15 123.0(8) . . . ? N3 C14 H14 119.4(9) . . . ? C15 C14 H14 117.6(9) . . . ? C14 C15 C16 118.4(8) . . . ? C14 C15 H15 121(1) . . . ? C16 C15 H15 121.0(9) . . . ? C15 C16 C17 119.3(9) . . . ? C15 C16 H16 119.7(9) . . . ? C17 C16 H16 120.9(9) . . . ? C16 C17 C18 118.8(8) . . . ? C16 C17 H17 119.6(9) . . . ? C18 C17 H17 121.6(9) . . . ? N3 C18 C17 122.6(8) . . . ? N3 C18 C19 115.9(7) . . . ? C17 C18 C19 121.4(8) . . . ? N4 C19 O2 127.9(8) . . . ? N4 C19 C18 113.6(7) . . . ? O2 C19 C18 118.6(8) . . . ? N4 C20 C21 119.2(8) . . . ? N4 C20 C25 119.9(8) . . . ? C21 C20 C25 120.8(8) . . . ? Cl21 C21 C20 119.4(8) . . . ? Cl21 C21 C22 121.0(9) . . . ? Cl21 C21 C262 12(1) . . . ? C20 C21 C22 119.5(8) . . . ? C20 C21 C262 119(2) . . . ? C22 C21 C262 121(2) . . . ? C21 C22 C23 119.4(9) . . . ? C21 C22 H22 121(1) . . . ? C23 C22 H22 120(1) . . . ? C22 C23 C24 121(1) . . . ? C22 C23 H23 119(1) . . . ? C24 C23 H23 120(1) . . . ? C23 C24 C25 121.4(9) . . . ? C23 C24 H24 119(1) . . . ? C25 C24 H24 120(1) . . . ? Cl2 C25 C20 121.4(9) . . . ? Cl2 C25 C24 120.5(9) . . . ? C20 C25 C24 117.9(9) . . . ? Cl21 C262 C21 120(6) . . . ? Cl11 C132 C12 91(3) . . . ? 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 O1w Co N2 C6 98.2(6) . . . . ? O1w Co N2 C7 -90.7(7) . . . . ? N4 Co N2 C6 -80.4(7) . . . . ? N4 Co N2 C7 90.7(7) . . . . ? O1w Co N4 C19 97.6(6) . . . . ? O1w Co N4 C20 -76.8(7) . . . . ? N2 Co N4 C19 -84.0(7) . . . . ? N2 Co N4 C20 101.6(7) . . . . ? C5 N1 C1 C2 0(1) . . . . ? C5 N1 C1 H1 176.5(9) . . . . ? C1 N1 C5 C4 0(1) . . . . ? C1 N1 C5 C6 -176.4(8) . . . . ? Co N2 C6 O1 173.6(8) . . . . ? Co N2 C6 C5 -8(1) . . . . ? C7 N2 C6 O1 2(1) . . . . ? C7 N2 C6 C5 -180.0(7) . . . . ? Co N2 C7 C8 83(1) . . . . ? Co N2 C7 C12 -89.5(9) . . . . ? C6 N2 C7 C8 -106(1) . . . . ? C6 N2 C7 C12 82(1) . . . . ? C18 N3 C14 C15 -2(1) . . . . ? C18 N3 C14 H14 178.0(8) . . . . ? C14 N3 C18 C17 1(1) . . . . ? C14 N3 C18 C19 -179.0(7) . . . . ? Co N4 C19 O2 177.9(7) . . . . ? Co N4 C19 C18 -2.1(9) . . . . ? C20 N4 C19 O2 -7(1) . . . . ? C20 N4 C19 C18 173.0(7) . . . . ? Co N4 C20 C21 86.3(9) . . . . ? Co N4 C20 C25 -89.4(9) . . . . ? C19 N4 C20 C21 -88(1) . . . . ? C19 N4 C20 C25 96(1) . . . . ? C131 Cl1 C8 C7 -180(15) . . . . ? C131 Cl1 C8 C9 -1(15) . . . . ? C132 Cl11 C12 C7 -100(4) . . . . ? C132 Cl11 C12 C11 91(4) . . . . ? C132 Cl11 C12 C132 0(4) . . . . ? C12 Cl11 C132 C12 .0(5) . . . . ? C261 Cl2 C25 C20 -80(9) . . . . ? C261 Cl2 C25 C24 106(8) . . . . ? C262 Cl21 C21 C20 92(8) . . . . ? C262 Cl21 C21 C22 -92(8) . . . . ? C262 Cl21 C21 C262 0(11) . . . . ? C21 Cl21 C262 C21 .0(6) . . . . ? N1 C1 C2 C3 0(1) . . . . ? N1 C1 C2 H2 -177(1) . . . . ? H1 C1 C2 C3 -176.6(9) . . . . ? H1 C1 C2 H2 6(2) . . . . ? C1 C2 C3 C4 0(2) . . . . ? C1 C2 C3 H3 178.7(9) . . . . ? H2 C2 C3 C4 177(1) . . . . ? H2 C2 C3 H3 -4(2) . . . . ? C2 C3 C4 C5 0(1) . . . . ? C2 C3 C4 H4 -180(1) . . . . ? H3 C3 C4 C5 -179.0(9) . . . . ? H3 C3 C4 H4 0(2) . . . . ? C3 C4 C5 N1 0(1) . . . . ? C3 C4 C5 C6 176.6(9) . . . . ? H4 C4 C5 N1 179.9(9) . . . . ? H4 C4 C5 C6 -3(1) . . . . ? N1 C5 C6 N2 -2(1) . . . . ? N1 C5 C6 O1 176.6(8) . . . . ? C4 C5 C6 N2 -178.8(8) . . . . ? C4 C5 C6 O1 0(1) . . . . ? N2 C7 C8 Cl1 1(1) . . . . ? N2 C7 C8 C9 -177.1(8) . . . . ? C12 C7 C8 Cl1 173.8(8) . . . . ? C12 C7 C8 C9 -5(1) . . . . ? N2 C7 C12 Cl11 7(1) . . . . ? N2 C7 C12 C11 176.9(8) . . . . ? N2 C7 C12 C132 -15(2) . . . . ? C8 C7 C12 Cl11 -165(1) . . . . ? C8 C7 C12 C11 4(1) . . . . ? C8 C7 C12 C132 172(1) . . . . ? Cl1 C8 C9 C10 -175.7(9) . . . . ? Cl1 C8 C9 H9 6(1) . . . . ? C7 C8 C9 C10 3(1) . . . . ? C7 C8 C9 H9 -175.3(9) . . . . ? C8 C9 C10 C11 0(1) . . . . ? C8 C9 C10 H10 178.0(9) . . . . ? H9 C9 C10 C11 177.5(9) . . . . ? H9 C9 C10 H10 -4(2) . . . . ? C9 C10 C11 C12 0(2) . . . . ? C9 C10 C11 H11 -179.7(9) . . . . ? H10 C10 C11 C12 -178(1) . . . . ? H10 C10 C11 H11 2(2) . . . . ? C10 C11 C12 Cl11 167(1) . . . . ? C10 C11 C12 C7 -2(2) . . . . ? C10 C11 C12 C132 -170(1) . . . . ? H11 C11 C12 Cl11 -13(2) . . . . ? H11 C11 C12 C7 177.8(9) . . . . ? H11 C11 C12 C132 10(2) . . . . ? Cl11 C12 C132 Cl11 0(3) . . . . ? C7 C12 C132 Cl11 91(4) . . . . ? C11 C12 C132 Cl11 -102(4) . . . . ? N3 C14 C15 C16 1(1) . . . . ? N3 C14 C15 H15 -179.1(8) . . . . ? H14 C14 C15 C16 -179.3(8) . . . . ? H14 C14 C15 H15 0(1) . . . . ? C14 C15 C16 C17 1(1) . . . . ? C14 C15 C16 H16 -179.1(9) . . . . ? H15 C15 C16 C17 -178.5(9) . . . . ? H15 C15 C16 H16 1(1) . . . . ? C15 C16 C17 C18 -2(1) . . . . ? C15 C16 C17 H17 178.7(9) . . . . ? H16 C16 C17 C18 178.2(8) . . . . ? H16 C16 C17 H17 -1(1) . . . . ? C16 C17 C18 N3 0(1) . . . . ? C16 C17 C18 C19 -178.7(8) . . . . ? H17 C17 C18 N3 -180.0(8) . . . . ? H17 C17 C18 C19 0(1) . . . . ? N3 C18 C19 N4 -8(1) . . . . ? N3 C18 C19 O2 171.8(7) . . . . ? C17 C18 C19 N4 171.4(8) . . . . ? C17 C18 C19 O2 -9(1) . . . . ? N4 C20 C21 Cl21 0(1) . . . . ? N4 C20 C21 C22 -176.1(8) . . . . ? N4 C20 C21 C262 13(2) . . . . ? C25 C20 C21 Cl21 175.5(8) . . . . ? C25 C20 C21 C22 0(1) . . . . ? C25 C20 C21 C262 -171(2) . . . . ? N4 C20 C25 Cl2 0(1) . . . . ? N4 C20 C25 C24 174.1(8) . . . . ? C21 C20 C25 Cl2 -175(1) . . . . ? C21 C20 C25 C24 -2(1) . . . . ? Cl21 C21 C22 C23 -175.0(9) . . . . ? Cl21 C21 C22 H22 5(2) . . . . ? C20 C21 C22 C23 0(1) . . . . ? C20 C21 C22 H22 -178.9(9) . . . . ? C262 C21 C22 C23 171(2) . . . . ? C262 C21 C22 H22 -8(2) . . . . ? Cl21 C21 C262 Cl21 0(3) . . . . ? C20 C21 C262 Cl21 -94(8) . . . . ? C22 C21 C262 Cl21 95(8) . . . . ? C21 C22 C23 C24 0(2) . . . . ? C21 C22 C23 H23 -177(1) . . . . ? H22 C22 C23 C24 -180(1) . . . . ? H22 C22 C23 H23 3(2) . . . . ? C22 C23 C24 C25 -3(2) . . . . ? C22 C23 C24 H24 176(1) . . . . ? H23 C23 C24 C25 175(1) . . . . ? H23 C23 C24 H24 -7(2) . . . . ? C23 C24 C25 Cl2 177(1) . . . . ? C23 C24 C25 C20 3(1) . . . . ? H24 C24 C25 Cl2 -2(2) . . . . ? H24 C24 C25 C20 -175.3(9) . . . . ? _reflns_limit_h_min 0 _reflns_limit_h_max 24 _reflns_limit_k_min -18 _reflns_limit_k_max 0 _reflns_limit_l_min 0 _reflns_limit_l_max 18 _reflns_number_total 4594 _reflns_number_observed 1978 _reflns_observed_criterion refl_observed_if_Inet_>_.000_sigma(Inet) _reflns_d_resolution_high .841 _reflns_d_resolution_low 10.52 loop_ _reflns_scale_group_code _reflns_scale_meas_F ? 4.0998 loop_ _refln_index_h _refln_index_k _refln_index_l _refln_F_meas _refln_F_calc _refln_F_sigma _refln_observed_status _refln_scale_group_code ? ? ? ? ? ? ? ?