# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_Fbtz _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C12 H8 F4 N6' _chemical_formula_sum 'C12 H8 F4 N6' _chemical_formula_weight 312.24 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c _symmetry_space_group_name_Hall '-P 2ybc' 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 9.6858(9) _cell_length_b 11.9624(11) _cell_length_c 11.1650(11) _cell_angle_alpha 90.00 _cell_angle_beta 103.899(2) _cell_angle_gamma 90.00 _cell_volume 1255.8(2) _cell_formula_units_Z 4 _cell_measurement_temperature 297(2) _cell_measurement_reflns_used 7878 _cell_measurement_theta_min 2.54 _cell_measurement_theta_max 27.37 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.652 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 632 _exptl_absorpt_coefficient_mu 0.149 _exptl_absorpt_correction_type MULTI-SCAN _exptl_absorpt_correction_T_min 0.9652 _exptl_absorpt_correction_T_max 0.9766 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 297(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 APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 20929 _diffrn_reflns_av_R_equivalents 0.1720 _diffrn_reflns_av_sigmaI/netI 0.0660 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.17 _diffrn_reflns_theta_max 27.69 _reflns_number_total 2932 _reflns_number_gt 2240 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1000P)^2^+0.9560P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2932 _refine_ls_number_parameters 199 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0737 _refine_ls_R_factor_gt 0.0589 _refine_ls_wR_factor_ref 0.1695 _refine_ls_wR_factor_gt 0.1492 _refine_ls_goodness_of_fit_ref 0.822 _refine_ls_restrained_S_all 0.822 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N1 N 0.90184(16) 0.40613(13) 0.22605(14) 0.0375(4) Uani 1 1 d . . . N2 N 0.78699(19) 0.46893(16) 0.23350(18) 0.0505(5) Uani 1 1 d . . . N3 N 0.8753(2) 0.52578(16) 0.07519(17) 0.0511(5) Uani 1 1 d . . . N4 N 0.59587(16) -0.15430(12) 0.27998(14) 0.0367(4) Uani 1 1 d . . . N5 N 0.71668(19) -0.21552(15) 0.29101(17) 0.0499(5) Uani 1 1 d . . . N6 N 0.5966(2) -0.27020(16) 0.43103(17) 0.0520(5) Uani 1 1 d . . . C1 C 0.9500(2) 0.31436(17) 0.31205(17) 0.0410(4) Uani 1 1 d . . . H1A H 0.9549 0.3396 0.3955 0.049 Uiso 1 1 calc R . . H1B H 1.0448 0.2918 0.3075 0.049 Uiso 1 1 calc R . . C2 C 0.85071(18) 0.21538(15) 0.28291(16) 0.0348(4) Uani 1 1 d . . . C3 C 0.7462(2) 0.19359(16) 0.34519(16) 0.0367(4) Uani 1 1 d . . . C4 C 0.65533(19) 0.10342(15) 0.31471(17) 0.0367(4) Uani 1 1 d . . . C5 C 0.66148(19) 0.03125(14) 0.21940(16) 0.0341(4) Uani 1 1 d . . . C6 C 0.7659(2) 0.05307(15) 0.15674(16) 0.0362(4) Uani 1 1 d . . . C7 C 0.85802(18) 0.14210(15) 0.18877(16) 0.0352(4) Uani 1 1 d . . . C8 C 0.5595(2) -0.06602(15) 0.18707(17) 0.0395(4) Uani 1 1 d . . . H8A H 0.4633 -0.0404 0.1820 0.047 Uiso 1 1 calc R . . H8B H 0.5633 -0.0956 0.1070 0.047 Uiso 1 1 calc R . . C11 C 0.7774(2) 0.53936(19) 0.1415(2) 0.0500(5) Uani 1 1 d . . . H11 H 0.7080 0.5946 0.1235 0.060 Uiso 1 1 calc R . . C12 C 0.9516(2) 0.44099(17) 0.13139(19) 0.0439(5) Uani 1 1 d . . . H12 H 1.0292 0.4100 0.1080 0.053 Uiso 1 1 calc R . . C13 C 0.5285(2) -0.18755(18) 0.36478(19) 0.0456(5) Uani 1 1 d . . . H13 H 0.4444 -0.1564 0.3756 0.055 Uiso 1 1 calc R . . C14 C 0.7106(2) -0.28378(19) 0.3817(2) 0.0516(5) Uani 1 1 d . . . H14 H 0.7798 -0.3378 0.4102 0.062 Uiso 1 1 calc R . . F1 F 0.73017(15) 0.26100(12) 0.43709(12) 0.0583(4) Uani 1 1 d . . . F2 F 0.55712(14) 0.08638(11) 0.37962(12) 0.0553(4) Uani 1 1 d . . . F3 F 0.95974(13) 0.15736(11) 0.12635(11) 0.0512(3) Uani 1 1 d . . . F4 F 0.78026(15) -0.01330(11) 0.06404(12) 0.0570(4) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.0338(8) 0.0331(8) 0.0488(9) -0.0039(6) 0.0164(6) -0.0058(6) N2 0.0433(9) 0.0476(10) 0.0682(11) 0.0026(8) 0.0285(8) 0.0041(8) N3 0.0491(10) 0.0499(11) 0.0582(10) 0.0080(8) 0.0206(8) -0.0004(8) N4 0.0345(8) 0.0282(8) 0.0485(8) 0.0004(6) 0.0118(6) -0.0012(6) N5 0.0447(10) 0.0424(10) 0.0677(11) 0.0101(8) 0.0237(8) 0.0116(8) N6 0.0520(10) 0.0482(11) 0.0583(10) 0.0110(8) 0.0181(8) -0.0023(8) C1 0.0358(9) 0.0406(11) 0.0456(10) 0.0001(8) 0.0076(7) -0.0079(8) C2 0.0324(9) 0.0316(9) 0.0400(9) 0.0041(7) 0.0076(7) -0.0014(7) C3 0.0385(9) 0.0350(9) 0.0380(9) -0.0040(7) 0.0120(7) -0.0006(7) C4 0.0351(9) 0.0348(9) 0.0435(9) 0.0010(7) 0.0158(7) -0.0011(7) C5 0.0343(8) 0.0259(8) 0.0416(9) 0.0033(7) 0.0081(7) 0.0011(7) C6 0.0402(9) 0.0311(9) 0.0384(9) -0.0006(7) 0.0117(7) 0.0033(7) C7 0.0319(8) 0.0368(9) 0.0397(9) 0.0059(7) 0.0138(7) 0.0026(7) C8 0.0376(9) 0.0316(9) 0.0466(10) 0.0013(7) 0.0050(7) -0.0032(7) C11 0.0440(11) 0.0427(11) 0.0661(13) 0.0044(10) 0.0188(10) 0.0028(9) C12 0.0402(10) 0.0433(11) 0.0531(11) 0.0031(8) 0.0210(8) 0.0000(8) C13 0.0392(10) 0.0446(11) 0.0564(11) 0.0033(9) 0.0185(9) -0.0011(8) C14 0.0490(12) 0.0445(12) 0.0640(13) 0.0136(10) 0.0186(10) 0.0086(9) F1 0.0622(8) 0.0570(8) 0.0633(8) -0.0264(6) 0.0300(6) -0.0156(6) F2 0.0492(7) 0.0590(8) 0.0683(8) -0.0102(6) 0.0349(6) -0.0135(6) F3 0.0429(7) 0.0608(8) 0.0572(7) -0.0004(6) 0.0267(5) -0.0043(6) F4 0.0686(9) 0.0496(8) 0.0601(7) -0.0182(6) 0.0298(6) -0.0060(6) _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 N1 C12 1.329(2) . ? N1 N2 1.361(2) . ? N1 C1 1.459(2) . ? N2 C11 1.314(3) . ? N3 C12 1.321(3) . ? N3 C11 1.346(3) . ? N4 C13 1.333(2) . ? N4 N5 1.361(2) . ? N4 C8 1.463(2) . ? N5 C14 1.313(3) . ? N6 C13 1.314(3) . ? N6 C14 1.357(3) . ? C1 C2 1.511(2) . ? C1 H1A 0.9700 . ? C1 H1B 0.9700 . ? C2 C7 1.383(3) . ? C2 C3 1.384(2) . ? C3 F1 1.343(2) . ? C3 C4 1.382(3) . ? C4 F2 1.343(2) . ? C4 C5 1.383(2) . ? C5 C6 1.385(2) . ? C5 C8 1.513(2) . ? C6 F4 1.338(2) . ? C6 C7 1.380(3) . ? C7 F3 1.3489(19) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C11 H11 0.9300 . ? C12 H12 0.9300 . ? C13 H13 0.9300 . ? C14 H14 0.9300 . ? 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 C12 N1 N2 109.45(16) . . ? C12 N1 C1 129.74(17) . . ? N2 N1 C1 120.78(16) . . ? C11 N2 N1 102.19(16) . . ? C12 N3 C11 102.62(17) . . ? C13 N4 N5 109.41(16) . . ? C13 N4 C8 130.05(16) . . ? N5 N4 C8 120.53(15) . . ? C14 N5 N4 102.00(16) . . ? C13 N6 C14 102.08(17) . . ? N1 C1 C2 111.18(15) . . ? N1 C1 H1A 109.4 . . ? C2 C1 H1A 109.4 . . ? N1 C1 H1B 109.4 . . ? C2 C1 H1B 109.4 . . ? H1A C1 H1B 108.0 . . ? C7 C2 C3 116.08(16) . . ? C7 C2 C1 120.93(16) . . ? C3 C2 C1 122.98(16) . . ? F1 C3 C4 118.26(16) . . ? F1 C3 C2 120.23(17) . . ? C4 C3 C2 121.51(16) . . ? F2 C4 C3 118.51(16) . . ? F2 C4 C5 119.19(16) . . ? C3 C4 C5 122.30(16) . . ? C4 C5 C6 116.26(16) . . ? C4 C5 C8 121.17(16) . . ? C6 C5 C8 122.57(16) . . ? F4 C6 C7 118.50(16) . . ? F4 C6 C5 120.20(17) . . ? C7 C6 C5 121.30(16) . . ? F3 C7 C6 118.53(16) . . ? F3 C7 C2 118.94(16) . . ? C6 C7 C2 122.53(16) . . ? N4 C8 C5 110.73(14) . . ? N4 C8 H8A 109.5 . . ? C5 C8 H8A 109.5 . . ? N4 C8 H8B 109.5 . . ? C5 C8 H8B 109.5 . . ? H8A C8 H8B 108.1 . . ? N2 C11 N3 115.2(2) . . ? N2 C11 H11 122.4 . . ? N3 C11 H11 122.4 . . ? N3 C12 N1 110.52(18) . . ? N3 C12 H12 124.7 . . ? N1 C12 H12 124.7 . . ? N6 C13 N4 111.03(18) . . ? N6 C13 H13 124.5 . . ? N4 C13 H13 124.5 . . ? N5 C14 N6 115.47(19) . . ? N5 C14 H14 122.3 . . ? N6 C14 H14 122.3 . . ? 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 C12 N1 N2 C11 -0.8(2) . . . . ? C1 N1 N2 C11 -179.07(17) . . . . ? C13 N4 N5 C14 1.3(2) . . . . ? C8 N4 N5 C14 -179.93(18) . . . . ? C12 N1 C1 C2 -104.3(2) . . . . ? N2 N1 C1 C2 73.6(2) . . . . ? N1 C1 C2 C7 79.8(2) . . . . ? N1 C1 C2 C3 -98.7(2) . . . . ? C7 C2 C3 F1 -179.28(16) . . . . ? C1 C2 C3 F1 -0.7(3) . . . . ? C7 C2 C3 C4 0.3(3) . . . . ? C1 C2 C3 C4 178.80(17) . . . . ? F1 C3 C4 F2 -1.1(3) . . . . ? C2 C3 C4 F2 179.35(17) . . . . ? F1 C3 C4 C5 178.30(17) . . . . ? C2 C3 C4 C5 -1.2(3) . . . . ? F2 C4 C5 C6 -179.56(16) . . . . ? C3 C4 C5 C6 1.0(3) . . . . ? F2 C4 C5 C8 0.1(3) . . . . ? C3 C4 C5 C8 -179.26(17) . . . . ? C4 C5 C6 F4 179.32(16) . . . . ? C8 C5 C6 F4 -0.4(3) . . . . ? C4 C5 C6 C7 0.1(3) . . . . ? C8 C5 C6 C7 -179.61(16) . . . . ? F4 C6 C7 F3 -0.9(3) . . . . ? C5 C6 C7 F3 178.33(16) . . . . ? F4 C6 C7 C2 179.69(16) . . . . ? C5 C6 C7 C2 -1.1(3) . . . . ? C3 C2 C7 F3 -178.52(16) . . . . ? C1 C2 C7 F3 2.9(3) . . . . ? C3 C2 C7 C6 0.9(3) . . . . ? C1 C2 C7 C6 -177.70(17) . . . . ? C13 N4 C8 C5 109.2(2) . . . . ? N5 N4 C8 C5 -69.3(2) . . . . ? C4 C5 C8 N4 -73.2(2) . . . . ? C6 C5 C8 N4 106.44(19) . . . . ? N1 N2 C11 N3 0.8(3) . . . . ? C12 N3 C11 N2 -0.5(3) . . . . ? C11 N3 C12 N1 -0.1(2) . . . . ? N2 N1 C12 N3 0.6(2) . . . . ? C1 N1 C12 N3 178.63(18) . . . . ? C14 N6 C13 N4 0.7(2) . . . . ? N5 N4 C13 N6 -1.4(2) . . . . ? C8 N4 C13 N6 -179.94(18) . . . . ? N4 N5 C14 N6 -0.9(3) . . . . ? C13 N6 C14 N5 0.2(3) . . . . ? 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 # #D H A D - H H...A D...A D - H...A symm(A) # C8 H8B N6 0.97 2.62 3.554(3) 163 4_555 yes C12 H12 N3 0.93 2.56 3.185(3) 125 3_765 yes C14 H14 F4 0.93 2.47 3.136(3) 128 4_556 yes _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.69 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.394 _refine_diff_density_min -0.317 _refine_diff_density_rms 0.074 _database_code_depnum_ccdc_archive 'CCDC 949172' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_1 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C24 H16 Cl2 F8 Mn N12' _chemical_formula_sum 'C24 H16 Cl2 F8 Mn N12' _chemical_formula_weight 750.33 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 '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' Mn Mn 0.3368 0.7283 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 26.5360(11) _cell_length_b 14.4560(6) _cell_length_c 8.0914(4) _cell_angle_alpha 90.00 _cell_angle_beta 106.9430(10) _cell_angle_gamma 90.00 _cell_volume 2969.2(2) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 4641 _cell_measurement_theta_min 2.79 _cell_measurement_theta_max 26.45 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.26 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.679 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1500 _exptl_absorpt_coefficient_mu 0.715 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8248 _exptl_absorpt_correction_T_max 0.8359 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 16458 _diffrn_reflns_av_R_equivalents 0.0327 _diffrn_reflns_av_sigmaI/netI 0.0269 _diffrn_reflns_limit_h_min -34 _diffrn_reflns_limit_h_max 34 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 1.60 _diffrn_reflns_theta_max 27.32 _reflns_number_total 3351 _reflns_number_gt 2679 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0452P)^2^+1.2215P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3351 _refine_ls_number_parameters 214 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0444 _refine_ls_R_factor_gt 0.0306 _refine_ls_wR_factor_ref 0.0883 _refine_ls_wR_factor_gt 0.0811 _refine_ls_goodness_of_fit_ref 1.053 _refine_ls_restrained_S_all 1.054 _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 Mn1 Mn 0.7500 0.2500 0.5000 0.02719(11) Uani 1 2 d SU . . C1 C 0.69392(8) 0.05790(14) 0.5677(3) 0.0422(5) Uani 1 1 d . . . H1 H 0.7176 0.0224 0.5300 0.051 Uiso 1 1 calc R . . C2 C 0.65448(8) 0.17302(14) 0.6256(3) 0.0393(5) Uani 1 1 d . . . H2 H 0.6436 0.2330 0.6388 0.047 Uiso 1 1 calc R . . C3 C 0.59026(8) 0.08744(16) 0.7454(3) 0.0418(5) Uani 1 1 d . . . H3A H 0.5802 0.1479 0.7769 0.050 Uiso 1 1 calc R . . H3B H 0.6018 0.0503 0.8495 0.050 Uiso 1 1 calc R . . C4 C 0.54349(7) 0.04193(14) 0.6192(2) 0.0338(4) Uani 1 1 d . . . C5 C 0.50607(8) 0.09332(13) 0.5015(3) 0.0367(5) Uani 1 1 d . . . C6 C 0.46354(7) 0.05294(14) 0.3841(3) 0.0351(4) Uani 1 1 d . . . C7 C 0.83380(9) 0.28060(15) 0.8783(3) 0.0469(5) Uani 1 1 d . . . H7 H 0.8302 0.3441 0.8600 0.056 Uiso 1 1 calc R . . C8 C 0.82373(8) 0.13915(13) 0.8376(3) 0.0376(4) Uani 1 1 d . . . H8 H 0.8128 0.0813 0.7901 0.045 Uiso 1 1 calc R . . C9 C 0.88494(7) 0.08650(13) 1.1226(3) 0.0364(4) Uani 1 1 d . . . H9A H 0.8778 0.0245 1.0758 0.044 Uiso 1 1 calc R . . H9B H 0.8705 0.0914 1.2195 0.044 Uiso 1 1 calc R . . C10 C 0.94404(7) 0.10077(12) 1.1868(2) 0.0318(4) Uani 1 1 d . . . C11 C 0.97547(8) 0.10323(13) 1.0772(2) 0.0341(4) Uani 1 1 d . . . C12 C 0.97024(8) 0.10423(13) 1.3613(3) 0.0342(4) Uani 1 1 d . . . Cl1 Cl 0.70915(2) 0.38618(3) 0.62174(8) 0.04287(14) Uani 1 1 d U . . F1 F 0.51135(6) 0.18574(8) 0.4994(2) 0.0625(4) Uani 1 1 d . . . F2 F 0.42893(5) 0.10638(9) 0.2703(2) 0.0574(4) Uani 1 1 d . . . F3 F 0.95290(5) 0.10141(9) 0.90515(15) 0.0492(3) Uani 1 1 d . . . F4 F 0.94246(5) 0.10456(9) 1.47660(16) 0.0504(3) Uani 1 1 d . . . N1 N 0.69330(6) 0.15105(11) 0.5612(2) 0.0347(4) Uani 1 1 d . . . N2 N 0.65829(7) 0.02130(12) 0.6317(3) 0.0458(4) Uani 1 1 d . . . N3 N 0.63337(6) 0.09716(11) 0.6686(2) 0.0345(4) Uani 1 1 d . . . N4 N 0.80680(6) 0.21864(11) 0.7620(2) 0.0363(4) Uani 1 1 d . . . N5 N 0.86566(8) 0.24493(11) 1.0194(3) 0.0501(5) Uani 1 1 d . . . N6 N 0.85844(6) 0.15290(10) 0.9906(2) 0.0325(3) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Mn1 0.02173(19) 0.0297(2) 0.0293(2) 0.00122(16) 0.00618(15) -0.00371(15) C1 0.0343(10) 0.0352(11) 0.0610(14) -0.0002(10) 0.0198(10) -0.0024(8) C2 0.0353(10) 0.0359(10) 0.0506(13) -0.0089(9) 0.0187(10) -0.0107(8) C3 0.0365(11) 0.0564(13) 0.0363(11) -0.0149(9) 0.0163(9) -0.0201(9) C4 0.0296(9) 0.0413(11) 0.0351(10) -0.0119(8) 0.0165(8) -0.0142(8) C5 0.0384(10) 0.0289(9) 0.0491(12) -0.0096(8) 0.0225(10) -0.0119(8) C6 0.0304(9) 0.0394(11) 0.0383(11) 0.0009(8) 0.0144(9) -0.0037(8) C7 0.0584(14) 0.0278(10) 0.0436(13) -0.0021(9) -0.0022(11) -0.0001(9) C8 0.0337(10) 0.0307(10) 0.0400(11) -0.0065(8) -0.0024(9) -0.0003(8) C9 0.0332(10) 0.0342(10) 0.0390(11) 0.0039(8) 0.0062(9) 0.0011(8) C10 0.0313(9) 0.0291(9) 0.0315(10) 0.0011(7) 0.0038(8) 0.0001(7) C11 0.0358(10) 0.0356(10) 0.0260(9) 0.0001(8) 0.0014(8) 0.0021(8) C12 0.0368(10) 0.0342(10) 0.0323(10) 0.0008(8) 0.0112(8) 0.0008(8) Cl1 0.0416(3) 0.0361(3) 0.0564(3) -0.0065(2) 0.0228(2) 0.0004(2) F1 0.0657(9) 0.0286(6) 0.0929(11) -0.0070(7) 0.0224(8) -0.0138(6) F2 0.0448(7) 0.0585(8) 0.0651(9) 0.0134(7) 0.0103(7) 0.0010(6) F3 0.0443(7) 0.0712(9) 0.0272(6) 0.0008(6) 0.0026(5) 0.0025(6) F4 0.0435(7) 0.0737(9) 0.0372(7) 0.0015(6) 0.0166(6) 0.0014(6) N1 0.0290(8) 0.0352(8) 0.0418(9) -0.0025(7) 0.0131(7) -0.0073(7) N2 0.0406(10) 0.0367(9) 0.0656(13) 0.0023(9) 0.0242(9) -0.0068(8) N3 0.0295(8) 0.0393(9) 0.0362(9) -0.0084(7) 0.0120(7) -0.0121(7) N4 0.0353(9) 0.0327(8) 0.0345(9) -0.0017(7) 0.0004(7) -0.0006(7) N5 0.0634(12) 0.0284(9) 0.0426(10) -0.0066(8) -0.0093(9) -0.0006(8) N6 0.0325(8) 0.0278(8) 0.0324(9) -0.0028(6) 0.0019(7) -0.0003(6) _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 Mn1 N1 2.2337(15) 7_656 ? Mn1 N1 2.2337(15) . ? Mn1 N4 2.2605(16) . ? Mn1 N4 2.2605(16) 7_656 ? Mn1 Cl1 2.5774(5) 7_656 ? Mn1 Cl1 2.5774(5) . ? C1 N2 1.314(2) . ? C1 N1 1.348(3) . ? C1 H1 0.9300 . ? C2 N1 1.321(2) . ? C2 N3 1.323(2) . ? C2 H2 0.9300 . ? C3 N3 1.459(2) . ? C3 C4 1.509(3) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 C5 1.376(3) . ? C4 C6 1.383(3) 5_656 ? C5 F1 1.344(2) . ? C5 C6 1.375(3) . ? C6 F2 1.340(2) . ? C6 C4 1.383(3) 5_656 ? C7 N5 1.312(3) . ? C7 N4 1.344(3) . ? C7 H7 0.9300 . ? C8 N4 1.318(2) . ? C8 N6 1.325(2) . ? C8 H8 0.9300 . ? C9 N6 1.456(2) . ? C9 C10 1.516(3) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 C12 1.381(3) . ? C10 C11 1.384(3) . ? C11 F3 1.346(2) . ? C11 C12 1.380(3) 2_757 ? C12 F4 1.347(2) . ? C12 C11 1.380(3) 2_757 ? N2 N3 1.358(2) . ? N5 N6 1.354(2) . ? 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 Mn1 N1 180.00(8) 7_656 . ? N1 Mn1 N4 91.63(6) 7_656 . ? N1 Mn1 N4 88.37(6) . . ? N1 Mn1 N4 88.37(6) 7_656 7_656 ? N1 Mn1 N4 91.63(6) . 7_656 ? N4 Mn1 N4 180.00(8) . 7_656 ? N1 Mn1 Cl1 91.08(4) 7_656 7_656 ? N1 Mn1 Cl1 88.92(4) . 7_656 ? N4 Mn1 Cl1 88.03(4) . 7_656 ? N4 Mn1 Cl1 91.97(4) 7_656 7_656 ? N1 Mn1 Cl1 88.92(4) 7_656 . ? N1 Mn1 Cl1 91.08(4) . . ? N4 Mn1 Cl1 91.97(4) . . ? N4 Mn1 Cl1 88.03(4) 7_656 . ? Cl1 Mn1 Cl1 180.00(2) 7_656 . ? N2 C1 N1 114.57(18) . . ? N2 C1 H1 122.7 . . ? N1 C1 H1 122.7 . . ? N1 C2 N3 110.06(17) . . ? N1 C2 H2 125.0 . . ? N3 C2 H2 125.0 . . ? N3 C3 C4 110.24(16) . . ? N3 C3 H3A 109.6 . . ? C4 C3 H3A 109.6 . . ? N3 C3 H3B 109.6 . . ? C4 C3 H3B 109.6 . . ? H3A C3 H3B 108.1 . . ? C5 C4 C6 117.11(17) . 5_656 ? C5 C4 C3 121.22(18) . . ? C6 C4 C3 121.67(19) 5_656 . ? F1 C5 C6 118.73(19) . . ? F1 C5 C4 119.25(18) . . ? C6 C5 C4 122.02(17) . . ? F2 C6 C5 119.34(18) . . ? F2 C6 C4 119.79(18) . 5_656 ? C5 C6 C4 120.87(19) . 5_656 ? N5 C7 N4 115.08(19) . . ? N5 C7 H7 122.5 . . ? N4 C7 H7 122.5 . . ? N4 C8 N6 110.67(17) . . ? N4 C8 H8 124.7 . . ? N6 C8 H8 124.7 . . ? N6 C9 C10 113.09(15) . . ? N6 C9 H9A 109.0 . . ? C10 C9 H9A 109.0 . . ? N6 C9 H9B 109.0 . . ? C10 C9 H9B 109.0 . . ? H9A C9 H9B 107.8 . . ? C12 C10 C11 115.88(17) . . ? C12 C10 C9 121.20(18) . . ? C11 C10 C9 122.70(17) . . ? F3 C11 C12 118.44(17) . 2_757 ? F3 C11 C10 119.53(17) . . ? C12 C11 C10 121.99(18) 2_757 . ? F4 C12 C11 118.35(17) . 2_757 ? F4 C12 C10 119.60(17) . . ? C11 C12 C10 121.99(18) 2_757 . ? C2 N1 C1 103.10(15) . . ? C2 N1 Mn1 125.90(13) . . ? C1 N1 Mn1 130.34(13) . . ? C1 N2 N3 102.34(16) . . ? C2 N3 N2 109.93(16) . . ? C2 N3 C3 129.52(18) . . ? N2 N3 C3 120.55(16) . . ? C8 N4 C7 102.48(17) . . ? C8 N4 Mn1 130.86(13) . . ? C7 N4 Mn1 126.61(14) . . ? C7 N5 N6 102.33(16) . . ? C8 N6 N5 109.44(16) . . ? C8 N6 C9 129.95(16) . . ? N5 N6 C9 120.52(16) . . ? 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 N3 C3 C4 C5 -88.0(2) . . . . ? N3 C3 C4 C6 91.7(2) . . . 5_656 ? C6 C4 C5 F1 -179.74(16) 5_656 . . . ? C3 C4 C5 F1 -0.1(3) . . . . ? C6 C4 C5 C6 -0.5(3) 5_656 . . . ? C3 C4 C5 C6 179.18(17) . . . . ? F1 C5 C6 F2 0.6(3) . . . . ? C4 C5 C6 F2 -178.66(17) . . . . ? F1 C5 C6 C4 179.76(16) . . . 5_656 ? C4 C5 C6 C4 0.5(3) . . . 5_656 ? N6 C9 C10 C12 130.86(19) . . . . ? N6 C9 C10 C11 -54.8(2) . . . . ? C12 C10 C11 F3 -179.10(16) . . . . ? C9 C10 C11 F3 6.2(3) . . . . ? C12 C10 C11 C12 3.2(2) . . . 2_757 ? C9 C10 C11 C12 -171.43(18) . . . 2_757 ? C11 C10 C12 F4 178.30(16) . . . . ? C9 C10 C12 F4 -7.0(3) . . . . ? C11 C10 C12 C11 -4.6(2) . . . 2_757 ? C9 C10 C12 C11 170.10(17) . . . 2_757 ? N3 C2 N1 C1 0.3(2) . . . . ? N3 C2 N1 Mn1 -171.24(13) . . . . ? N2 C1 N1 C2 -0.1(3) . . . . ? N2 C1 N1 Mn1 170.86(15) . . . . ? N4 Mn1 N1 C2 95.56(17) . . . . ? N4 Mn1 N1 C2 -84.44(17) 7_656 . . . ? Cl1 Mn1 N1 C2 -176.38(17) 7_656 . . . ? Cl1 Mn1 N1 C2 3.62(17) . . . . ? N4 Mn1 N1 C1 -73.54(19) . . . . ? N4 Mn1 N1 C1 106.46(19) 7_656 . . . ? Cl1 Mn1 N1 C1 14.51(18) 7_656 . . . ? Cl1 Mn1 N1 C1 -165.49(18) . . . . ? N1 C1 N2 N3 -0.1(3) . . . . ? N1 C2 N3 N2 -0.3(2) . . . . ? N1 C2 N3 C3 179.31(18) . . . . ? C1 N2 N3 C2 0.2(2) . . . . ? C1 N2 N3 C3 -179.43(18) . . . . ? C4 C3 N3 C2 113.7(2) . . . . ? C4 C3 N3 N2 -66.7(3) . . . . ? N6 C8 N4 C7 0.5(2) . . . . ? N6 C8 N4 Mn1 177.98(13) . . . . ? N5 C7 N4 C8 -0.4(3) . . . . ? N5 C7 N4 Mn1 -178.00(16) . . . . ? N1 Mn1 N4 C8 -129.64(18) 7_656 . . . ? N1 Mn1 N4 C8 50.36(18) . . . . ? Cl1 Mn1 N4 C8 -38.62(18) 7_656 . . . ? Cl1 Mn1 N4 C8 141.38(18) . . . . ? N1 Mn1 N4 C7 47.27(18) 7_656 . . . ? N1 Mn1 N4 C7 -132.73(18) . . . . ? Cl1 Mn1 N4 C7 138.30(18) 7_656 . . . ? Cl1 Mn1 N4 C7 -41.70(18) . . . . ? N4 C7 N5 N6 0.1(3) . . . . ? N4 C8 N6 N5 -0.5(2) . . . . ? N4 C8 N6 C9 176.00(18) . . . . ? C7 N5 N6 C8 0.2(2) . . . . ? C7 N5 N6 C9 -176.65(18) . . . . ? C10 C9 N6 C8 130.4(2) . . . . ? C10 C9 N6 N5 -53.4(3) . . . . ? 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 # #D H A D - H H...A D...A D - H...A symm(A) # C3 H3A N5 0.97 2.41 3.093(3) 127 7_657 yes C3 H3B N2 0.97 2.56 3.495(3) 163 6_556 yes C7 H7 N2 0.93 2.58 3.488(3) 166 4_656 yes C9 H9B Cl1 0.97 2.79 3.699(2) 155 7_657 yes _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 27.32 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.245 _refine_diff_density_min -0.209 _refine_diff_density_rms 0.049 _database_code_depnum_ccdc_archive 'CCDC 949173' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_2 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C24 H16 Cl2 Co F8 N12' _chemical_formula_weight 754.32 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' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Co Co 0.3494 0.9721 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 26.278(6) _cell_length_b 14.401(3) _cell_length_c 8.0107(19) _cell_angle_alpha 90.00 _cell_angle_beta 107.248(5) _cell_angle_gamma 90.00 _cell_volume 2895.1(11) _cell_formula_units_Z 4 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 2780 _cell_measurement_theta_min 2.82 _cell_measurement_theta_max 28.40 _exptl_crystal_description BLOCK _exptl_crystal_colour pink _exptl_crystal_size_max 0.21 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.731 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1508 _exptl_absorpt_coefficient_mu 0.870 _exptl_absorpt_correction_type MULTI-SCAN _exptl_absorpt_correction_T_min 0.8383 _exptl_absorpt_correction_T_max 0.8733 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 295(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 APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 7585 _diffrn_reflns_av_R_equivalents 0.0476 _diffrn_reflns_av_sigmaI/netI 0.0494 _diffrn_reflns_limit_h_min -31 _diffrn_reflns_limit_h_max 31 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -5 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 1.62 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2546 _reflns_number_gt 1918 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1000P)^2^+0.2500P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment CONSTR _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2546 _refine_ls_number_parameters 214 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0653 _refine_ls_R_factor_gt 0.0453 _refine_ls_wR_factor_ref 0.1475 _refine_ls_wR_factor_gt 0.1224 _refine_ls_goodness_of_fit_ref 1.021 _refine_ls_restrained_S_all 1.021 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Co1 Co 0.2500 0.2500 0.0000 0.0300(2) Uani 1 2 d S . . Cl1 Cl 0.28986(4) 0.11566(6) -0.12385(13) 0.0428(3) Uani 1 1 d . . . N1 N 0.35669(11) 0.15432(19) 0.4806(4) 0.0357(7) Uani 1 1 d . . . N2 N 0.30486(12) 0.2210(2) 0.2499(4) 0.0361(7) Uani 1 1 d . . . N3 N 0.36365(16) 0.2458(2) 0.5116(5) 0.0517(10) Uani 1 1 d . . . N4 N 0.19572(12) 0.15455(19) 0.0593(4) 0.0351(7) Uani 1 1 d . . . N5 N 0.13475(12) 0.1000(2) 0.1648(4) 0.0360(7) Uani 1 1 d . . . N6 N 0.15933(13) 0.0243(2) 0.1241(5) 0.0471(8) Uani 1 1 d . . . C1 C 0.33129(17) 0.2823(3) 0.3687(5) 0.0482(10) Uani 1 1 d . . . H1 H 0.3272 0.3460 0.3519 0.058 Uiso 1 1 calc R . . C2 C 0.32231(15) 0.1407(2) 0.3251(5) 0.0382(9) Uani 1 1 d . . . H2 H 0.3118 0.0828 0.2755 0.046 Uiso 1 1 calc R . . C3 C 0.38364(14) 0.0872(2) 0.6143(5) 0.0375(8) Uani 1 1 d . . . H3A H 0.3766 0.0251 0.5658 0.045 Uiso 1 1 calc R . . H3B H 0.3688 0.0914 0.7114 0.045 Uiso 1 1 calc R . . C4 C 0.44311(15) 0.1016(2) 0.6820(5) 0.0348(8) Uani 1 1 d . . . C5 C 0.46932(16) 0.1056(2) 0.8600(5) 0.0379(9) Uani 1 1 d . . . C6 C 0.52421(15) 0.1049(2) 0.9252(4) 0.0367(9) Uani 1 1 d . . . C7 C 0.19571(15) 0.0610(3) 0.0617(5) 0.0444(9) Uani 1 1 d . . . H7 H 0.2194 0.0255 0.0226 0.053 Uiso 1 1 calc R . . C8 C 0.15639(15) 0.1771(2) 0.1241(5) 0.0391(9) Uani 1 1 d . . . H8 H 0.1456 0.2373 0.1388 0.047 Uiso 1 1 calc R . . C9 C 0.09161(15) 0.0904(3) 0.2428(5) 0.0457(10) Uani 1 1 d . . . H9A H 0.0813 0.1513 0.2730 0.055 Uiso 1 1 calc R . . H9B H 0.1038 0.0543 0.3494 0.055 Uiso 1 1 calc R . . C10 C 0.04413(14) 0.0433(3) 0.1185(5) 0.0360(8) Uani 1 1 d . . . C11 C 0.00537(16) 0.0933(2) -0.0013(5) 0.0405(9) Uani 1 1 d . . . C12 C -0.03753(14) 0.0525(3) -0.1164(5) 0.0372(8) Uani 1 1 d . . . F1 F 0.01000(10) 0.18677(15) -0.0063(4) 0.0652(7) Uani 1 1 d . . . F2 F -0.07356(10) 0.10422(16) -0.2327(3) 0.0582(7) Uani 1 1 d . . . F3 F 0.44059(9) 0.10477(18) 0.9740(3) 0.0525(6) Uani 1 1 d . . . F4 F 0.54630(9) 0.10214(17) 1.1003(3) 0.0516(6) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Co1 0.0329(4) 0.0226(4) 0.0315(4) 0.0008(3) 0.0048(3) -0.0029(3) Cl1 0.0502(6) 0.0283(5) 0.0533(6) -0.0061(4) 0.0204(5) -0.0007(4) N1 0.0436(18) 0.0231(15) 0.0350(16) -0.0010(13) 0.0034(14) 0.0006(13) N2 0.0402(17) 0.0282(16) 0.0348(16) -0.0005(13) 0.0031(14) -0.0018(13) N3 0.070(2) 0.0263(17) 0.0430(19) -0.0052(14) -0.0077(18) -0.0007(15) N4 0.0401(17) 0.0235(15) 0.0411(17) -0.0023(13) 0.0112(14) -0.0077(13) N5 0.0415(17) 0.0292(16) 0.0369(17) -0.0042(13) 0.0111(14) -0.0104(13) N6 0.0486(19) 0.0322(18) 0.064(2) -0.0006(16) 0.0213(17) -0.0054(15) C1 0.065(3) 0.0200(18) 0.046(2) 0.0014(17) -0.005(2) 0.0010(18) C2 0.044(2) 0.0210(17) 0.040(2) -0.0042(16) -0.0027(16) 0.0004(15) C3 0.044(2) 0.0245(18) 0.039(2) 0.0049(15) 0.0056(17) 0.0021(15) C4 0.045(2) 0.0187(17) 0.0358(19) 0.0000(14) 0.0047(16) 0.0010(14) C5 0.050(2) 0.0280(19) 0.035(2) 0.0008(15) 0.0114(17) 0.0013(16) C6 0.048(2) 0.0281(19) 0.0254(18) 0.0026(14) -0.0026(16) 0.0011(15) C7 0.044(2) 0.032(2) 0.059(2) 0.0021(18) 0.0174(19) -0.0010(17) C8 0.044(2) 0.0240(18) 0.051(2) -0.0039(17) 0.0161(18) -0.0093(16) C9 0.046(2) 0.052(2) 0.040(2) -0.0121(19) 0.0153(18) -0.0169(19) C10 0.040(2) 0.0317(19) 0.040(2) -0.0102(16) 0.0184(17) -0.0098(15) C11 0.053(2) 0.0187(17) 0.057(2) -0.0042(17) 0.027(2) -0.0085(16) C12 0.040(2) 0.029(2) 0.043(2) -0.0012(16) 0.0143(17) -0.0027(16) F1 0.0774(17) 0.0215(11) 0.094(2) -0.0058(13) 0.0217(15) -0.0127(11) F2 0.0581(15) 0.0452(14) 0.0649(16) 0.0095(12) 0.0084(13) 0.0007(11) F3 0.0534(14) 0.0638(17) 0.0412(13) -0.0007(11) 0.0153(11) -0.0017(11) F4 0.0577(15) 0.0600(16) 0.0309(11) -0.0016(10) 0.0036(10) 0.0001(11) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Co1 N2 2.133(3) 7 ? Co1 N2 2.133(3) . ? Co1 N4 2.133(3) 7 ? Co1 N4 2.133(3) . ? Co1 Cl1 2.5378(10) . ? Co1 Cl1 2.5378(10) 7 ? N1 C2 1.319(4) . ? N1 N3 1.343(4) . ? N1 C3 1.461(4) . ? N2 C2 1.321(5) . ? N2 C1 1.332(5) . ? N3 C1 1.315(5) . ? N4 C8 1.327(5) . ? N4 C7 1.347(5) . ? N5 C8 1.331(5) . ? N5 N6 1.356(4) . ? N5 C9 1.454(5) . ? N6 C7 1.314(5) . ? C1 H1 0.9300 . ? C2 H2 0.9300 . ? C3 C4 1.509(5) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 C6 1.383(6) 2_656 ? C4 C5 1.389(5) . ? C5 F3 1.347(4) . ? C5 C6 1.381(5) . ? C6 F4 1.350(4) . ? C6 C4 1.383(6) 2_656 ? C7 H7 0.9300 . ? C8 H8 0.9300 . ? C9 C10 1.508(5) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 C11 1.377(5) . ? C10 C12 1.390(5) 5 ? C11 F1 1.353(4) . ? C11 C12 1.360(5) . ? C12 F2 1.340(4) . ? C12 C10 1.390(5) 5 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N2 Co1 N2 180.0(2) 7 . ? N2 Co1 N4 88.58(12) 7 7 ? N2 Co1 N4 91.42(12) . 7 ? N2 Co1 N4 91.42(12) 7 . ? N2 Co1 N4 88.58(12) . . ? N4 Co1 N4 180.00(11) 7 . ? N2 Co1 Cl1 91.43(9) 7 . ? N2 Co1 Cl1 88.57(9) . . ? N4 Co1 Cl1 91.34(8) 7 . ? N4 Co1 Cl1 88.66(8) . . ? N2 Co1 Cl1 88.56(9) 7 7 ? N2 Co1 Cl1 91.44(9) . 7 ? N4 Co1 Cl1 88.66(8) 7 7 ? N4 Co1 Cl1 91.34(8) . 7 ? Cl1 Co1 Cl1 180.0 . 7 ? C2 N1 N3 109.7(3) . . ? C2 N1 C3 129.9(3) . . ? N3 N1 C3 120.3(3) . . ? C2 N2 C1 102.5(3) . . ? C2 N2 Co1 130.3(3) . . ? C1 N2 Co1 127.2(3) . . ? C1 N3 N1 102.3(3) . . ? C8 N4 C7 103.6(3) . . ? C8 N4 Co1 125.4(2) . . ? C7 N4 Co1 130.6(2) . . ? C8 N5 N6 110.1(3) . . ? C8 N5 C9 128.9(3) . . ? N6 N5 C9 121.0(3) . . ? C7 N6 N5 102.7(3) . . ? N3 C1 N2 115.0(3) . . ? N3 C1 H1 122.5 . . ? N2 C1 H1 122.5 . . ? N1 C2 N2 110.4(3) . . ? N1 C2 H2 124.8 . . ? N2 C2 H2 124.8 . . ? N1 C3 C4 113.4(3) . . ? N1 C3 H3A 108.9 . . ? C4 C3 H3A 108.9 . . ? N1 C3 H3B 108.9 . . ? C4 C3 H3B 108.9 . . ? H3A C3 H3B 107.7 . . ? C6 C4 C5 115.2(3) 2_656 . ? C6 C4 C3 123.3(3) 2_656 . ? C5 C4 C3 121.3(3) . . ? F3 C5 C6 118.4(3) . . ? F3 C5 C4 119.3(3) . . ? C6 C5 C4 122.2(4) . . ? F4 C6 C5 118.2(3) . . ? F4 C6 C4 119.3(3) . 2_656 ? C5 C6 C4 122.4(3) . 2_656 ? N6 C7 N4 114.3(3) . . ? N6 C7 H7 122.8 . . ? N4 C7 H7 122.8 . . ? N4 C8 N5 109.3(3) . . ? N4 C8 H8 125.4 . . ? N5 C8 H8 125.4 . . ? N5 C9 C10 110.9(3) . . ? N5 C9 H9A 109.5 . . ? C10 C9 H9A 109.5 . . ? N5 C9 H9B 109.5 . . ? C10 C9 H9B 109.5 . . ? H9A C9 H9B 108.0 . . ? C11 C10 C12 116.6(3) . 5 ? C11 C10 C9 121.4(3) . . ? C12 C10 C9 122.0(4) 5 . ? F1 C11 C12 118.3(4) . . ? F1 C11 C10 119.1(3) . . ? C12 C11 C10 122.6(3) . . ? F2 C12 C11 120.2(3) . . ? F2 C12 C10 118.9(3) . 5 ? C11 C12 C10 120.8(3) . 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 N4 Co1 N2 C2 -129.5(3) 7 . . . ? N4 Co1 N2 C2 50.5(3) . . . . ? Cl1 Co1 N2 C2 -38.1(3) . . . . ? Cl1 Co1 N2 C2 141.9(3) 7 . . . ? N4 Co1 N2 C1 48.8(3) 7 . . . ? N4 Co1 N2 C1 -131.2(3) . . . . ? Cl1 Co1 N2 C1 140.1(3) . . . . ? Cl1 Co1 N2 C1 -39.9(3) 7 . . . ? C2 N1 N3 C1 0.9(5) . . . . ? C3 N1 N3 C1 -176.4(3) . . . . ? N2 Co1 N4 C8 -84.1(3) 7 . . . ? N2 Co1 N4 C8 95.9(3) . . . . ? Cl1 Co1 N4 C8 -175.5(3) . . . . ? Cl1 Co1 N4 C8 4.5(3) 7 . . . ? N2 Co1 N4 C7 104.5(3) 7 . . . ? N2 Co1 N4 C7 -75.5(3) . . . . ? Cl1 Co1 N4 C7 13.1(3) . . . . ? Cl1 Co1 N4 C7 -166.9(3) 7 . . . ? C8 N5 N6 C7 0.8(4) . . . . ? C9 N5 N6 C7 -178.7(3) . . . . ? N1 N3 C1 N2 -0.5(5) . . . . ? C2 N2 C1 N3 -0.1(5) . . . . ? Co1 N2 C1 N3 -178.8(3) . . . . ? N3 N1 C2 N2 -1.0(5) . . . . ? C3 N1 C2 N2 175.9(3) . . . . ? C1 N2 C2 N1 0.7(4) . . . . ? Co1 N2 C2 N1 179.3(2) . . . . ? C2 N1 C3 C4 129.9(4) . . . . ? N3 N1 C3 C4 -53.5(5) . . . . ? N1 C3 C4 C6 -54.9(5) . . . 2_656 ? N1 C3 C4 C5 130.0(3) . . . . ? C6 C4 C5 F3 178.6(3) 2_656 . . . ? C3 C4 C5 F3 -5.9(5) . . . . ? C6 C4 C5 C6 -5.3(4) 2_656 . . . ? C3 C4 C5 C6 170.2(3) . . . . ? F3 C5 C6 F4 0.9(5) . . . . ? C4 C5 C6 F4 -175.2(3) . . . . ? F3 C5 C6 C4 177.1(3) . . . 2_656 ? C4 C5 C6 C4 1.0(5) . . . 2_656 ? N5 N6 C7 N4 -0.3(5) . . . . ? C8 N4 C7 N6 -0.3(5) . . . . ? Co1 N4 C7 N6 172.5(3) . . . . ? C7 N4 C8 N5 0.8(4) . . . . ? Co1 N4 C8 N5 -172.5(2) . . . . ? N6 N5 C8 N4 -1.0(4) . . . . ? C9 N5 C8 N4 178.4(3) . . . . ? C8 N5 C9 C10 116.1(4) . . . . ? N6 N5 C9 C10 -64.5(5) . . . . ? N5 C9 C10 C11 -88.2(4) . . . . ? N5 C9 C10 C12 90.8(4) . . . 5 ? C12 C10 C11 F1 -179.4(3) 5 . . . ? C9 C10 C11 F1 -0.4(5) . . . . ? C12 C10 C11 C12 0.2(6) 5 . . . ? C9 C10 C11 C12 179.2(3) . . . . ? F1 C11 C12 F2 0.9(6) . . . . ? C10 C11 C12 F2 -178.7(3) . . . . ? F1 C11 C12 C10 179.4(3) . . . 5 ? C10 C11 C12 C10 -0.2(6) . . . 5 ? 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 # #D H A D - H H...A D...A D - H...A symm(A) # C1 H1 N6 0.93 2.59 3.493(5) 164 4_555 yes C3 H3B Cl1 0.97 2.79 3.702(4) 157 1_556 yes C7 H7 Cl1 0.93 2.79 3.336(4) 119 . yes C8 H8 Cl1 0.93 2.74 3.302(3) 120 7_555 yes C9 H9A N3 0.97 2.41 3.073(5) 126 7_556 yes C9 H9B N6 0.97 2.52 3.464(5) 165 6_556 yes _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.724 _refine_diff_density_min -0.467 _refine_diff_density_rms 0.090 _database_code_depnum_ccdc_archive 'CCDC 949174' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_3 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C24 H16 Cl2 Co F8 N12, C H2 Cl2, H2 O' _chemical_formula_sum 'C25 H18 Cl4 Co F8 N12' _chemical_formula_weight 839.24 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 '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' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pbam loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z' '-x+1/2, y+1/2, -z' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x, y, -z' 'x-1/2, -y-1/2, z' '-x-1/2, y-1/2, z' _cell_length_a 19.385(12) _cell_length_b 7.570(5) _cell_length_c 11.540(7) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1693.4(18) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 1728 _cell_measurement_theta_min 2.74 _cell_measurement_theta_max 21.33 _exptl_crystal_description PRISM _exptl_crystal_colour blue _exptl_crystal_size_max 0.21 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.646 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 838 _exptl_absorpt_coefficient_mu 0.906 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8326 _exptl_absorpt_correction_T_max 0.8837 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9139 _diffrn_reflns_av_R_equivalents 0.1221 _diffrn_reflns_av_sigmaI/netI 0.0728 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 23 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 1.76 _diffrn_reflns_theta_max 25.50 _reflns_number_total 1661 _reflns_number_gt 1172 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1028P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1661 _refine_ls_number_parameters 121 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0911 _refine_ls_R_factor_gt 0.0569 _refine_ls_wR_factor_ref 0.1682 _refine_ls_wR_factor_gt 0.1498 _refine_ls_goodness_of_fit_ref 1.002 _refine_ls_restrained_S_all 1.002 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Co1 Co 0.0000 0.0000 0.0000 0.0429(4) Uani 1 4 d S . . N1 N 0.06910(16) 0.1148(4) 0.1257(3) 0.0502(9) Uani 1 1 d . . . N2 N 0.13621(19) 0.3077(4) 0.2048(3) 0.0591(10) Uani 1 1 d . . . N3 N 0.1664(3) 0.1521(5) 0.2254(5) 0.1027(19) Uani 1 1 d . . . Cl1 Cl 0.06850(7) -0.28216(16) 0.0000 0.0533(5) Uani 1 2 d S . . Cl2 Cl 0.43036(19) 0.5585(6) 0.5000 0.193(2) Uani 1 2 d S . . C1 C 0.1242(3) 0.0408(6) 0.1758(6) 0.0856(19) Uani 1 1 d . . . H1 H 0.1318 -0.0805 0.1753 0.103 Uiso 1 1 calc R . . C2 C 0.0785(2) 0.2820(5) 0.1472(4) 0.0570(12) Uani 1 1 d . . . H2 H 0.0483 0.3714 0.1249 0.068 Uiso 1 1 calc R . . C3 C 0.1672(3) 0.4722(5) 0.2484(5) 0.0694(14) Uani 1 1 d . . . H3A H 0.1409 0.5724 0.2202 0.083 Uiso 1 1 calc R . . H3B H 0.2139 0.4828 0.2193 0.083 Uiso 1 1 calc R . . C4 C 0.1681(2) 0.4742(4) 0.3771(5) 0.0565(12) Uani 1 1 d . . . C5 C 0.1135(2) 0.5412(5) 0.4404(5) 0.0678(15) Uani 1 1 d . . . C6 C 0.22291(19) 0.4130(4) 0.4407(4) 0.0486(10) Uani 1 1 d . . . F1 F 0.05866(14) 0.6064(4) 0.3827(4) 0.1031(12) Uani 1 1 d . . . F2 F 0.27896(12) 0.3494(3) 0.3850(2) 0.0659(8) Uani 1 1 d . . . C7 C 0.5000 0.5000 0.573(2) 0.128(8) Uani 0.50 2 d SP . . H7A H 0.5010 0.6131 0.6120 0.153 Uiso 0.25 1 d PR . . H7B H 0.4743 0.4079 0.6120 0.153 Uiso 0.25 1 d PR . . 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 0.0405(6) 0.0284(5) 0.0598(8) 0.000 0.000 0.0049(4) N1 0.0518(19) 0.0368(17) 0.062(2) -0.0003(16) -0.0076(16) 0.0045(14) N2 0.059(2) 0.0376(17) 0.080(3) 0.0089(17) -0.0175(19) 0.0006(15) N3 0.103(3) 0.049(2) 0.156(5) -0.009(3) -0.073(3) 0.018(2) Cl1 0.0492(8) 0.0301(7) 0.0806(11) 0.000 0.000 0.0089(5) Cl2 0.109(2) 0.144(3) 0.325(6) 0.000 0.000 0.023(2) C1 0.087(4) 0.040(2) 0.130(5) -0.002(3) -0.051(4) 0.013(2) C2 0.051(2) 0.035(2) 0.084(3) 0.003(2) -0.017(2) -0.0003(17) C3 0.067(3) 0.041(2) 0.100(4) 0.016(2) -0.021(3) -0.020(2) C4 0.051(2) 0.0254(18) 0.093(4) 0.006(2) -0.013(2) -0.0115(17) C5 0.041(2) 0.0364(19) 0.126(4) 0.008(2) -0.017(2) -0.0055(17) C6 0.046(2) 0.0252(16) 0.075(3) -0.0012(16) 0.0007(18) -0.0024(16) F1 0.0553(17) 0.0761(19) 0.178(4) 0.017(2) -0.0346(19) 0.0076(14) F2 0.0610(15) 0.0484(13) 0.088(2) 0.0009(13) 0.0105(13) 0.0071(12) C7 0.14(2) 0.090(13) 0.15(2) 0.000 0.000 -0.034(13) _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(3) . ? Co1 N1 2.157(3) 5 ? Co1 N1 2.157(3) 2 ? Co1 N1 2.157(3) 6 ? Co1 Cl1 2.5149(17) . ? Co1 Cl1 2.5149(17) 5 ? N1 C2 1.303(5) . ? N1 C1 1.337(6) . ? N2 C2 1.316(5) . ? N2 N3 1.337(5) . ? N2 C3 1.471(5) . ? N3 C1 1.307(6) . ? Cl2 C7 1.649(13) . ? Cl2 C7 1.649(13) 5_666 ? C1 H1 0.9300 . ? C2 H2 0.9300 . ? C3 C4 1.485(7) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 C6 1.372(6) . ? C4 C5 1.383(7) . ? C5 F1 1.347(5) . ? C5 C5 1.376(11) 6_556 ? C6 F2 1.351(4) . ? C6 C6 1.369(9) 6_556 ? C7 Cl2 1.649(13) 5_666 ? C7 C7 1.68(5) 5_666 ? C7 H7A 0.9700 . ? C7 H7B 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 N1 Co1 N1 180.00(19) . 5 ? N1 Co1 N1 95.50(19) . 2 ? N1 Co1 N1 84.50(19) 5 2 ? N1 Co1 N1 84.50(19) . 6 ? N1 Co1 N1 95.50(19) 5 6 ? N1 Co1 N1 180.00(19) 2 6 ? N1 Co1 Cl1 90.81(9) . . ? N1 Co1 Cl1 89.19(9) 5 . ? N1 Co1 Cl1 89.19(9) 2 . ? N1 Co1 Cl1 90.81(9) 6 . ? N1 Co1 Cl1 89.19(9) . 5 ? N1 Co1 Cl1 90.81(9) 5 5 ? N1 Co1 Cl1 90.81(9) 2 5 ? N1 Co1 Cl1 89.19(9) 6 5 ? Cl1 Co1 Cl1 180.00(5) . 5 ? C2 N1 C1 102.3(3) . . ? C2 N1 Co1 127.3(3) . . ? C1 N1 Co1 128.2(3) . . ? C2 N2 N3 109.4(3) . . ? C2 N2 C3 130.1(4) . . ? N3 N2 C3 120.4(4) . . ? C1 N3 N2 102.4(4) . . ? C7 Cl2 C7 61.1(15) . 5_666 ? N3 C1 N1 114.8(4) . . ? N3 C1 H1 122.6 . . ? N1 C1 H1 122.6 . . ? N1 C2 N2 111.0(4) . . ? N1 C2 H2 124.5 . . ? N2 C2 H2 124.5 . . ? N2 C3 C4 110.8(4) . . ? N2 C3 H3A 109.5 . . ? C4 C3 H3A 109.5 . . ? N2 C3 H3B 109.5 . . ? C4 C3 H3B 109.5 . . ? H3A C3 H3B 108.1 . . ? C6 C4 C5 115.7(5) . . ? C6 C4 C3 122.8(4) . . ? C5 C4 C3 121.5(4) . . ? F1 C5 C5 119.6(3) . 6_556 ? F1 C5 C4 118.5(5) . . ? C5 C5 C4 121.9(3) 6_556 . ? F2 C6 C6 118.4(2) . 6_556 ? F2 C6 C4 119.2(4) . . ? C6 C6 C4 122.3(3) 6_556 . ? Cl2 C7 Cl2 118.9(15) . 5_666 ? Cl2 C7 C7 59.5(7) . 5_666 ? Cl2 C7 C7 59.5(7) 5_666 5_666 ? Cl2 C7 H7A 91.0 . . ? Cl2 C7 H7A 117.3 5_666 . ? C7 C7 H7A 118.0 5_666 . ? Cl2 C7 H7B 90.6 . . ? Cl2 C7 H7B 117.8 5_666 . ? C7 C7 H7B 118.0 5_666 . ? H7A C7 H7B 115.1 . . ? 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 C2 -35(58) 5 . . . ? N1 Co1 N1 C2 -111.6(4) 2 . . . ? N1 Co1 N1 C2 68.4(4) 6 . . . ? Cl1 Co1 N1 C2 159.2(4) . . . . ? Cl1 Co1 N1 C2 -20.8(4) 5 . . . ? N1 Co1 N1 C1 164(59) 5 . . . ? N1 Co1 N1 C1 88.3(5) 2 . . . ? N1 Co1 N1 C1 -91.7(5) 6 . . . ? Cl1 Co1 N1 C1 -0.9(5) . . . . ? Cl1 Co1 N1 C1 179.1(5) 5 . . . ? C2 N2 N3 C1 1.0(7) . . . . ? C3 N2 N3 C1 179.1(5) . . . . ? N2 N3 C1 N1 -0.3(8) . . . . ? C2 N1 C1 N3 -0.5(7) . . . . ? Co1 N1 C1 N3 163.4(5) . . . . ? C1 N1 C2 N2 1.1(6) . . . . ? Co1 N1 C2 N2 -163.0(3) . . . . ? N3 N2 C2 N1 -1.4(6) . . . . ? C3 N2 C2 N1 -179.3(5) . . . . ? C2 N2 C3 C4 113.7(5) . . . . ? N3 N2 C3 C4 -63.9(6) . . . . ? N2 C3 C4 C6 91.5(5) . . . . ? N2 C3 C4 C5 -89.5(5) . . . . ? C6 C4 C5 F1 178.8(3) . . . . ? C3 C4 C5 F1 -0.3(5) . . . . ? C6 C4 C5 C5 -1.9(4) . . . 6_556 ? C3 C4 C5 C5 179.0(2) . . . 6_556 ? C5 C4 C6 F2 -178.4(3) . . . . ? C3 C4 C6 F2 0.7(5) . . . . ? C5 C4 C6 C6 1.9(4) . . . 6_556 ? C3 C4 C6 C6 -179.0(2) . . . 6_556 ? C7 Cl2 C7 Cl2 0.0 5_666 . . 5_666 ? 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 # #D H A D - H H...A D...A D - H...A symm(A) # C1 H1 Cl1 0.9300 2.8200 3.355(6) 118.00 . yes C2 H2 Cl1 0.9300 2.7700 3.318(5) 119.00 2_555 yes # SQUEEZE RESULTS (APPEND TO CIF) # Note: Data are Listed for all Voids in the P1 Unit Cell # i.e. Centre of Gravity, Solvent Accessible Volume, # Recovered number of Electrons in the Void and # Details about the Squeezed Material loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons _platon_squeeze_void_content 1 0.250 -0.015 0.000 76 10 ' ' 2 0.750 -0.036 0.000 76 10 ' ' _platon_squeeze_details ; ; _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.478 _refine_diff_density_min -0.568 _refine_diff_density_rms 0.136 _database_code_depnum_ccdc_archive 'CCDC 949175' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_4 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C24 H16 Cl2 F8 Fe N12, 2(C0.50 H Cl)' _chemical_formula_sum 'C25 H18 Cl4 F8 Fe N12' _chemical_formula_weight 836.16 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' F F 0.0171 0.0103 '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' Fe Fe 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pnma loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z' 'x+1/2, -y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z' '-x-1/2, y-1/2, z-1/2' _cell_length_a 19.5396(16) _cell_length_b 23.505(2) _cell_length_c 7.5642(6) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3474.1(5) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 3491 _cell_measurement_theta_min 2.26 _cell_measurement_theta_max 25.20 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.599 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1672 _exptl_absorpt_coefficient_mu 0.823 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8397 _exptl_absorpt_correction_T_max 0.8660 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 19504 _diffrn_reflns_av_R_equivalents 0.0500 _diffrn_reflns_av_sigmaI/netI 0.0400 _diffrn_reflns_limit_h_min -24 _diffrn_reflns_limit_h_max 24 _diffrn_reflns_limit_k_min -28 _diffrn_reflns_limit_k_max 28 _diffrn_reflns_limit_l_min -6 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 1.73 _diffrn_reflns_theta_max 26.00 _reflns_number_total 3501 _reflns_number_gt 2582 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0571P)^2^+3.3220P] 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 3501 _refine_ls_number_parameters 244 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0735 _refine_ls_R_factor_gt 0.0507 _refine_ls_wR_factor_ref 0.1331 _refine_ls_wR_factor_gt 0.1219 _refine_ls_goodness_of_fit_ref 1.004 _refine_ls_restrained_S_all 1.004 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Fe1 Fe 0.51155(3) 0.2500 0.98393(8) 0.0402(2) Uani 1 2 d S . . N1 N 0.57987(14) 0.31410(12) 0.8694(3) 0.0483(7) Uani 1 1 d . . . N2 N 0.64403(15) 0.35886(13) 0.6812(3) 0.0576(8) Uani 1 1 d . . . N3 N 0.6722(2) 0.36997(19) 0.8406(4) 0.0971(14) Uani 1 1 d . . . N4 N 0.44250(14) 0.31392(12) 1.0991(3) 0.0495(7) Uani 1 1 d . . . N5 N 0.3473(2) 0.36602(19) 1.1312(4) 0.0971(14) Uani 1 1 d . . . N6 N 0.37372(16) 0.35182(13) 1.2906(3) 0.0579(8) Uani 1 1 d . . . C1 C 0.58927(17) 0.32638(15) 0.7019(4) 0.0527(9) Uani 1 1 d . . . H1 H 0.5613 0.3140 0.6103 0.063 Uiso 1 1 calc R . . C2 C 0.6316(2) 0.3418(2) 0.9483(5) 0.0828(14) Uani 1 1 d . . . H2 H 0.6383 0.3411 1.0700 0.099 Uiso 1 1 calc R . . C3 C 0.6735(2) 0.38356(17) 0.5203(4) 0.0666(11) Uani 1 1 d . . . H3A H 0.6484 0.3699 0.4182 0.080 Uiso 1 1 calc R . . H3B H 0.7207 0.3713 0.5086 0.080 Uiso 1 1 calc R . . C4 C 0.67089(18) 0.44698(16) 0.5246(4) 0.0530(9) Uani 1 1 d . . . C5 C 0.61483(18) 0.4767(2) 0.4610(5) 0.0650(11) Uani 1 1 d . . . C6 C 0.61211(18) 0.5356(2) 0.4672(5) 0.0664(11) Uani 1 1 d . . . C7 C 0.66454(18) 0.56754(17) 0.5358(4) 0.0538(9) Uani 1 1 d . . . C8 C 0.72107(17) 0.53784(15) 0.5960(4) 0.0486(8) Uani 1 1 d . . . C9 C 0.72440(17) 0.47957(16) 0.5903(4) 0.0493(8) Uani 1 1 d . . . C10 C 0.3396(2) 0.36922(17) 1.4532(5) 0.0678(11) Uani 1 1 d . . . H10A H 0.3646 0.3547 1.5543 0.081 Uiso 1 1 calc R . . H10B H 0.2938 0.3533 1.4564 0.081 Uiso 1 1 calc R . . C11 C 0.42978(17) 0.32198(15) 1.2688(4) 0.0515(8) Uani 1 1 d . . . H11 H 0.4569 0.3083 1.3604 0.062 Uiso 1 1 calc R . . C12 C 0.3905(2) 0.3419(2) 1.0221(5) 0.0853(15) Uani 1 1 d . . . H12 H 0.3855 0.3440 0.9000 0.102 Uiso 1 1 calc R . . C13 C 0.4964(9) 0.4691(8) 1.001(2) 0.152(7) Uani 0.50 1 d P . . H13A H 0.5063 0.4442 1.0982 0.182 Uiso 0.50 1 d PR . . H13B H 0.4814 0.4468 0.9018 0.182 Uiso 0.50 1 d PR . . Cl1 Cl 0.44291(6) 0.2500 0.70067(14) 0.0499(3) Uani 1 2 d S . . Cl2 Cl 0.57894(6) 0.2500 1.26993(15) 0.0546(3) Uani 1 2 d S . . Cl3 Cl 0.5701(5) 0.5009(7) 0.9436(14) 0.175(4) Uani 0.50 1 d P . . Cl4 Cl 0.4355(6) 0.5118(9) 1.054(2) 0.269(8) Uani 0.50 1 d P . . F1 F 0.78044(10) 0.45316(9) 0.6509(3) 0.0643(6) Uani 1 1 d . . . F2 F 0.77435(10) 0.56640(9) 0.6625(3) 0.0630(6) Uani 1 1 d . . . F3 F 0.55676(11) 0.56146(14) 0.4023(4) 0.1026(10) Uani 1 1 d . . . F4 F 0.56232(12) 0.44741(14) 0.3926(3) 0.1015(9) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Fe1 0.0380(3) 0.0505(4) 0.0321(3) 0.000 0.0011(3) 0.000 N1 0.0496(16) 0.0596(17) 0.0357(14) -0.0022(13) 0.0025(12) -0.0110(13) N2 0.0600(18) 0.077(2) 0.0360(15) -0.0062(14) 0.0067(13) -0.0216(16) N3 0.099(3) 0.147(4) 0.0454(19) 0.005(2) -0.0093(19) -0.074(3) N4 0.0511(16) 0.0621(17) 0.0353(14) 0.0005(13) -0.0010(12) 0.0100(13) N5 0.105(3) 0.141(4) 0.0455(19) -0.003(2) -0.0120(19) 0.069(3) N6 0.0648(19) 0.0727(19) 0.0364(15) 0.0057(14) 0.0052(13) 0.0230(16) C1 0.054(2) 0.065(2) 0.0395(18) -0.0050(16) -0.0006(15) -0.0199(17) C2 0.093(3) 0.119(4) 0.0356(19) 0.005(2) -0.006(2) -0.055(3) C3 0.072(3) 0.087(3) 0.0405(19) -0.0061(19) 0.0206(18) -0.021(2) C4 0.054(2) 0.074(2) 0.0310(16) -0.0034(16) 0.0121(15) -0.0131(18) C5 0.0365(19) 0.121(3) 0.0380(18) -0.006(2) 0.0036(15) -0.017(2) C6 0.0391(19) 0.115(3) 0.045(2) 0.004(2) 0.0061(16) 0.018(2) C7 0.052(2) 0.079(2) 0.0310(16) 0.0006(17) 0.0092(15) 0.0122(18) C8 0.052(2) 0.067(2) 0.0271(15) -0.0029(15) 0.0033(14) -0.0027(17) C9 0.0453(18) 0.073(2) 0.0300(16) 0.0052(16) 0.0037(14) 0.0033(17) C10 0.077(3) 0.081(3) 0.045(2) 0.0096(19) 0.0223(19) 0.020(2) C11 0.049(2) 0.068(2) 0.0376(17) 0.0046(16) -0.0031(14) 0.0120(17) C12 0.107(4) 0.114(4) 0.0345(19) 0.002(2) -0.006(2) 0.054(3) C13 0.126(12) 0.22(2) 0.104(10) 0.004(13) -0.025(9) -0.067(14) Cl1 0.0477(6) 0.0686(7) 0.0333(6) 0.000 -0.0061(5) 0.000 Cl2 0.0480(7) 0.0813(8) 0.0347(6) 0.000 -0.0044(5) 0.000 Cl3 0.097(5) 0.316(11) 0.113(5) 0.005(5) 0.024(4) -0.066(6) Cl4 0.157(10) 0.46(2) 0.191(11) 0.002(11) 0.035(8) 0.094(10) F1 0.0584(12) 0.0772(14) 0.0571(12) 0.0057(11) -0.0090(10) 0.0060(10) F2 0.0647(13) 0.0732(13) 0.0510(11) -0.0025(10) -0.0101(10) -0.0122(11) F3 0.0503(14) 0.172(3) 0.0858(18) 0.0112(18) -0.0044(12) 0.0318(16) F4 0.0565(14) 0.167(3) 0.0807(17) -0.0119(18) -0.0071(13) -0.0401(16) _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 Fe1 N1 2.191(3) 7_565 ? Fe1 N1 2.191(3) . ? Fe1 N4 2.199(3) . ? Fe1 N4 2.199(3) 7_565 ? Fe1 Cl1 2.5279(12) . ? Fe1 Cl2 2.5326(13) . ? N1 C1 1.312(4) . ? N1 C2 1.343(4) . ? N2 C1 1.324(4) . ? N2 N3 1.351(4) . ? N2 C3 1.466(4) . ? N3 C2 1.316(5) . ? N4 C11 1.321(4) . ? N4 C12 1.344(5) . ? N5 C12 1.309(5) . ? N5 N6 1.354(4) . ? N6 C11 1.311(4) . ? N6 C10 1.458(4) . ? C1 H1 0.9300 . ? C2 H2 0.9300 . ? C3 C4 1.492(5) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 C5 1.385(5) . ? C4 C9 1.388(5) . ? C5 F4 1.339(4) . ? C5 C6 1.387(6) . ? C6 F3 1.334(4) . ? C6 C7 1.372(5) . ? C7 C8 1.384(5) . ? C7 C10 1.491(5) 5_667 ? C8 F2 1.337(4) . ? C8 C9 1.372(5) . ? C9 F1 1.340(4) . ? C10 C7 1.491(5) 5_667 ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 H11 0.9300 . ? C12 H12 0.9300 . ? C13 C13 1.46(4) 5_667 ? C13 Cl4 1.465(17) 5_667 ? C13 Cl3 1.54(3) 5_667 ? C13 Cl4 1.61(3) . ? C13 Cl3 1.678(18) . ? C13 H13A 0.9600 . ? C13 H13B 0.9599 . ? Cl3 Cl4 0.32(3) 5_667 ? Cl3 C13 1.54(3) 5_667 ? Cl4 Cl3 0.32(3) 5_667 ? Cl4 C13 1.465(17) 5_667 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 Fe1 N1 86.86(15) 7_565 . ? N1 Fe1 N4 179.64(11) 7_565 . ? N1 Fe1 N4 93.48(11) . . ? N1 Fe1 N4 93.48(11) 7_565 7_565 ? N1 Fe1 N4 179.64(11) . 7_565 ? N4 Fe1 N4 86.18(15) . 7_565 ? N1 Fe1 Cl1 89.31(7) 7_565 . ? N1 Fe1 Cl1 89.31(7) . . ? N4 Fe1 Cl1 90.59(7) . . ? N4 Fe1 Cl1 90.59(7) 7_565 . ? N1 Fe1 Cl2 91.21(7) 7_565 . ? N1 Fe1 Cl2 91.21(7) . . ? N4 Fe1 Cl2 88.88(7) . . ? N4 Fe1 Cl2 88.88(7) 7_565 . ? Cl1 Fe1 Cl2 179.28(5) . . ? C1 N1 C2 102.5(3) . . ? C1 N1 Fe1 128.2(2) . . ? C2 N1 Fe1 128.0(2) . . ? C1 N2 N3 109.6(3) . . ? C1 N2 C3 130.1(3) . . ? N3 N2 C3 120.3(3) . . ? C2 N3 N2 102.1(3) . . ? C11 N4 C12 102.0(3) . . ? C11 N4 Fe1 126.8(2) . . ? C12 N4 Fe1 128.8(2) . . ? C12 N5 N6 102.1(3) . . ? C11 N6 N5 109.7(3) . . ? C11 N6 C10 129.7(3) . . ? N5 N6 C10 120.5(3) . . ? N1 C1 N2 110.7(3) . . ? N1 C1 H1 124.6 . . ? N2 C1 H1 124.6 . . ? N3 C2 N1 115.0(3) . . ? N3 C2 H2 122.5 . . ? N1 C2 H2 122.5 . . ? N2 C3 C4 111.4(3) . . ? N2 C3 H3A 109.4 . . ? C4 C3 H3A 109.4 . . ? N2 C3 H3B 109.4 . . ? C4 C3 H3B 109.4 . . ? H3A C3 H3B 108.0 . . ? C5 C4 C9 116.2(4) . . ? C5 C4 C3 121.5(4) . . ? C9 C4 C3 122.2(4) . . ? F4 C5 C4 118.8(4) . . ? F4 C5 C6 119.8(4) . . ? C4 C5 C6 121.5(3) . . ? F3 C6 C7 119.7(4) . . ? F3 C6 C5 118.3(4) . . ? C7 C6 C5 122.0(3) . . ? C6 C7 C8 116.4(4) . . ? C6 C7 C10 121.8(4) . 5_667 ? C8 C7 C10 121.8(4) . 5_667 ? F2 C8 C9 118.4(3) . . ? F2 C8 C7 119.5(3) . . ? C9 C8 C7 122.1(3) . . ? F1 C9 C8 119.4(3) . . ? F1 C9 C4 118.9(3) . . ? C8 C9 C4 121.8(3) . . ? N6 C10 C7 110.6(3) . 5_667 ? N6 C10 H10A 109.5 . . ? C7 C10 H10A 109.5 5_667 . ? N6 C10 H10B 109.5 . . ? C7 C10 H10B 109.5 5_667 . ? H10A C10 H10B 108.1 . . ? N6 C11 N4 110.9(3) . . ? N6 C11 H11 124.6 . . ? N4 C11 H11 124.6 . . ? N5 C12 N4 115.2(3) . . ? N5 C12 H12 122.4 . . ? N4 C12 H12 122.4 . . ? C13 C13 Cl4 66.7(13) 5_667 5_667 ? C13 C13 Cl3 68.0(17) 5_667 5_667 ? Cl4 C13 Cl3 134.7(18) 5_667 5_667 ? C13 C13 Cl4 56.7(14) 5_667 . ? Cl4 C13 Cl4 123.5(13) 5_667 . ? Cl3 C13 Cl4 11.2(10) 5_667 . ? C13 C13 Cl3 58.2(13) 5_667 . ? Cl4 C13 Cl3 8.5(13) 5_667 . ? Cl3 C13 Cl3 126.2(12) 5_667 . ? Cl4 C13 Cl3 114.9(15) . . ? C13 C13 H13A 126.4 5_667 . ? Cl4 C13 H13A 102.9 5_667 . ? Cl3 C13 H13A 103.9 5_667 . ? Cl4 C13 H13A 109.7 . . ? Cl3 C13 H13A 107.3 . . ? C13 C13 H13B 124.5 5_667 . ? Cl4 C13 H13B 103.0 5_667 . ? Cl3 C13 H13B 101.9 5_667 . ? Cl4 C13 H13B 108.0 . . ? Cl3 C13 H13B 107.7 . . ? H13A C13 H13B 109.1 . . ? Cl4 Cl3 C13 97(4) 5_667 5_667 ? Cl4 Cl3 C13 43(4) 5_667 . ? C13 Cl3 C13 53.8(12) 5_667 . ? Cl3 Cl4 C13 128(5) 5_667 5_667 ? Cl3 Cl4 C13 72(5) 5_667 . ? C13 Cl4 C13 56.5(13) 5_667 . ? 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 Fe1 N1 C1 68.9(3) 7_565 . . . ? N4 Fe1 N1 C1 -111.0(3) . . . . ? N4 Fe1 N1 C1 -94(17) 7_565 . . . ? Cl1 Fe1 N1 C1 -20.4(3) . . . . ? Cl2 Fe1 N1 C1 160.1(3) . . . . ? N1 Fe1 N1 C2 -96.1(4) 7_565 . . . ? N4 Fe1 N1 C2 84.0(4) . . . . ? N4 Fe1 N1 C2 101(17) 7_565 . . . ? Cl1 Fe1 N1 C2 174.5(4) . . . . ? Cl2 Fe1 N1 C2 -5.0(4) . . . . ? C1 N2 N3 C2 0.9(5) . . . . ? C3 N2 N3 C2 178.9(4) . . . . ? N1 Fe1 N4 C11 80(17) 7_565 . . . ? N1 Fe1 N4 C11 -117.1(3) . . . . ? N4 Fe1 N4 C11 63.0(3) 7_565 . . . ? Cl1 Fe1 N4 C11 153.6(3) . . . . ? Cl2 Fe1 N4 C11 -25.9(3) . . . . ? N1 Fe1 N4 C12 -80(17) 7_565 . . . ? N1 Fe1 N4 C12 83.7(4) . . . . ? N4 Fe1 N4 C12 -96.2(4) 7_565 . . . ? Cl1 Fe1 N4 C12 -5.7(4) . . . . ? Cl2 Fe1 N4 C12 174.8(4) . . . . ? C12 N5 N6 C11 1.1(5) . . . . ? C12 N5 N6 C10 -178.3(4) . . . . ? C2 N1 C1 N2 0.9(4) . . . . ? Fe1 N1 C1 N2 -167.2(2) . . . . ? N3 N2 C1 N1 -1.2(5) . . . . ? C3 N2 C1 N1 -178.9(4) . . . . ? N2 N3 C2 N1 -0.4(6) . . . . ? C1 N1 C2 N3 -0.3(6) . . . . ? Fe1 N1 C2 N3 167.8(3) . . . . ? C1 N2 C3 C4 115.9(4) . . . . ? N3 N2 C3 C4 -61.6(5) . . . . ? N2 C3 C4 C5 -89.0(4) . . . . ? N2 C3 C4 C9 91.6(4) . . . . ? C9 C4 C5 F4 178.6(3) . . . . ? C3 C4 C5 F4 -0.7(5) . . . . ? C9 C4 C5 C6 -1.5(5) . . . . ? C3 C4 C5 C6 179.2(3) . . . . ? F4 C5 C6 F3 -0.6(5) . . . . ? C4 C5 C6 F3 179.5(3) . . . . ? F4 C5 C6 C7 -180.0(3) . . . . ? C4 C5 C6 C7 0.2(5) . . . . ? F3 C6 C7 C8 -178.2(3) . . . . ? C5 C6 C7 C8 1.1(5) . . . . ? F3 C6 C7 C10 2.5(5) . . . 5_667 ? C5 C6 C7 C10 -178.2(3) . . . 5_667 ? C6 C7 C8 F2 179.2(3) . . . . ? C10 C7 C8 F2 -1.5(5) 5_667 . . . ? C6 C7 C8 C9 -1.0(5) . . . . ? C10 C7 C8 C9 178.3(3) 5_667 . . . ? F2 C8 C9 F1 0.0(4) . . . . ? C7 C8 C9 F1 -179.9(3) . . . . ? F2 C8 C9 C4 179.4(3) . . . . ? C7 C8 C9 C4 -0.4(5) . . . . ? C5 C4 C9 F1 -178.9(3) . . . . ? C3 C4 C9 F1 0.4(5) . . . . ? C5 C4 C9 C8 1.6(5) . . . . ? C3 C4 C9 C8 -179.0(3) . . . . ? C11 N6 C10 C7 120.1(4) . . . 5_667 ? N5 N6 C10 C7 -60.7(5) . . . 5_667 ? N5 N6 C11 N4 -1.3(5) . . . . ? C10 N6 C11 N4 178.0(4) . . . . ? C12 N4 C11 N6 0.9(4) . . . . ? Fe1 N4 C11 N6 -162.7(2) . . . . ? N6 N5 C12 N4 -0.5(6) . . . . ? C11 N4 C12 N5 -0.2(6) . . . . ? Fe1 N4 C12 N5 162.9(3) . . . . ? C13 C13 Cl3 Cl4 -178(7) 5_667 . . 5_667 ? Cl3 C13 Cl3 Cl4 -178(7) 5_667 . . 5_667 ? Cl4 C13 Cl3 Cl4 -178(6) . . . 5_667 ? Cl4 C13 Cl3 C13 178(7) 5_667 . . 5_667 ? Cl3 C13 Cl3 C13 0.0 5_667 . . 5_667 ? Cl4 C13 Cl3 C13 -0.3(11) . . . 5_667 ? C13 C13 Cl4 Cl3 178(5) 5_667 . . 5_667 ? Cl4 C13 Cl4 Cl3 178(5) 5_667 . . 5_667 ? Cl3 C13 Cl4 Cl3 179(4) . . . 5_667 ? Cl4 C13 Cl4 C13 0.000(1) 5_667 . . 5_667 ? Cl3 C13 Cl4 C13 -178(5) 5_667 . . 5_667 ? Cl3 C13 Cl4 C13 0.3(11) . . . 5_667 ? 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 # #D H A D - H H...A D...A D - H...A symm(A) # C13 H13A F4 0.9600 2.4800 3.270(16) 139.00 1_556 yes C13 H13B F3 0.9600 2.4300 3.302(16) 151.00 5_666 yes # SQUEEZE RESULTS (APPEND TO CIF) # Note: Data are Listed for all Voids in the P1 Unit Cell # i.e. Centre of Gravity, Solvent Accessible Volume, # Recovered number of Electrons in the Void and # Details about the Squeezed Material loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons _platon_squeeze_void_content 1 0.243 0.750 -0.025 88 17 ' ' 2 0.257 0.250 -0.029 88 17 ' ' 3 0.743 0.750 -0.018 88 17 ' ' 4 0.757 0.250 -0.048 88 17 ' ' _platon_squeeze_details ; ; _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.440 _refine_diff_density_min -0.371 _refine_diff_density_rms 0.054 _database_code_depnum_ccdc_archive 'CCDC 949176' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_5 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C24 H16 Cl2 Cu F8 N12, 4(H2 O)' _chemical_formula_sum 'C24 H24 Cl2 Cu F8 N12 O4' _chemical_formula_weight 830.99 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' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 '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 orthorhombic _symmetry_space_group_name_H-M Pnma loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z+1/2' '-x, y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' '-x-1/2, y-1/2, z-1/2' 'x, -y-1/2, z' _cell_length_a 19.282(8) _cell_length_b 23.511(9) _cell_length_c 7.617(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3453(2) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 4147 _cell_measurement_theta_min 2.285 _cell_measurement_theta_max 25.802 _exptl_crystal_description block _exptl_crystal_colour blue _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.598 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1676 _exptl_absorpt_coefficient_mu 0.881 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8298 _exptl_absorpt_correction_T_max 0.8866 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 ? _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 21921 _diffrn_reflns_av_R_equivalents 0.0943 _diffrn_reflns_av_sigmaI/netI 0.0635 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 24 _diffrn_reflns_limit_k_min -30 _diffrn_reflns_limit_k_max 30 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 1.73 _diffrn_reflns_theta_max 27.89 _reflns_number_total 4170 _reflns_number_gt 2810 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1611P)^2^+4.9643P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0070(15) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 4170 _refine_ls_number_parameters 242 _refine_ls_number_restraints 6 _refine_ls_R_factor_all 0.1282 _refine_ls_R_factor_gt 0.0884 _refine_ls_wR_factor_ref 0.2831 _refine_ls_wR_factor_gt 0.2520 _refine_ls_goodness_of_fit_ref 1.092 _refine_ls_restrained_S_all 1.094 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu 0.47086(5) 0.2500 0.49722(11) 0.0393(3) Uani 1 2 d S . . N1 N 0.3438(2) 0.14187(17) 0.7777(5) 0.0435(10) Uani 1 1 d . . . N2 N 0.3188(3) 0.1295(2) 0.6174(6) 0.0611(14) Uani 1 1 d . . . N3 N 0.4075(2) 0.19012(16) 0.5993(5) 0.0387(9) Uani 1 1 d . . . N4 N 0.3951(3) -0.14451(18) 0.7721(6) 0.0510(12) Uani 1 1 d . . . N5 N 0.3758(3) -0.1290(2) 0.6087(7) 0.0694(16) Uani 1 1 d . . . N6 N 0.4654(2) -0.18997(17) 0.6009(5) 0.0416(10) Uani 1 1 d . . . Cl1 Cl 0.54583(10) 0.2500 0.8184(2) 0.0464(5) Uani 1 2 d S . . Cl2 Cl 0.39987(11) 0.2500 0.1816(2) 0.0506(5) Uani 1 2 d S . . C1 C 0.3965(3) 0.1775(2) 0.7663(6) 0.0416(11) Uani 1 1 d . . . H1 H 0.4218 0.1915 0.8607 0.050 Uiso 1 1 calc R . . C2 C 0.3593(4) 0.1601(3) 0.5152(7) 0.0570(16) Uani 1 1 d . . . H2 H 0.3546 0.1606 0.3937 0.068 Uiso 1 1 calc R . . C3 C 0.3120(3) 0.1174(2) 0.9343(7) 0.0478(13) Uani 1 1 d . . . H3A H 0.2627 0.1260 0.9356 0.057 Uiso 1 1 calc R . . H3B H 0.3327 0.1339 1.0385 0.057 Uiso 1 1 calc R . . C4 C 0.3226(3) 0.0539(2) 0.9348(6) 0.0423(12) Uani 1 1 d . . . C5 C 0.2748(3) 0.0170(2) 0.8641(6) 0.0414(11) Uani 1 1 d . . . C6 C 0.2856(3) -0.0405(2) 0.8603(6) 0.0458(12) Uani 1 1 d . . . C7 C 0.3438(3) -0.0646(2) 0.9289(7) 0.0511(14) Uani 1 1 d . . . C8 C 0.3908(3) -0.0276(3) 1.0049(7) 0.0589(17) Uani 1 1 d . . . C9 C 0.3802(3) 0.0300(3) 1.0075(7) 0.0536(14) Uani 1 1 d . . . C10 C 0.3547(4) -0.1278(2) 0.9240(8) 0.0624(17) Uani 1 1 d . . . H10A H 0.3785 -0.1397 1.0300 0.075 Uiso 1 1 calc R . . H10B H 0.3100 -0.1467 0.9207 0.075 Uiso 1 1 calc R . . C11 C 0.4478(3) -0.1806(2) 0.7650(7) 0.0439(12) Uani 1 1 d . . . H11 H 0.4693 -0.1969 0.8621 0.053 Uiso 1 1 calc R . . C12 C 0.4200(4) -0.1571(3) 0.5121(7) 0.0623(18) Uani 1 1 d . . . H12 H 0.4202 -0.1546 0.3902 0.075 Uiso 1 1 calc R . . F1 F 0.4272(2) 0.0633(2) 1.0830(7) 0.0850(13) Uani 1 1 d . . . F2 F 0.4475(2) -0.0497(2) 1.0836(8) 0.0977(16) Uani 1 1 d . . . F3 F 0.2369(2) -0.07314(14) 0.7878(4) 0.0662(10) Uani 1 1 d . . . F4 F 0.2167(2) 0.03834(14) 0.7980(5) 0.0628(10) Uani 1 1 d . . . O1 O 0.5647(3) 0.9739(3) 0.4565(9) 0.122(3) Uani 1 1 d . . . H1A H 0.5353 0.9517 0.4930 0.183 Uiso 1 1 d R . . H1B H 0.5574 1.0082 0.4525 0.183 Uiso 1 1 d R . . O2 O 0.2310(10) 0.2500 0.208(4) 0.331(16) Uani 1 2 d S . . H2A H 0.2496 0.2804 0.1838 0.497 Uiso 1 1 d R . . O3 O 0.2072(12) 0.2240(9) 0.788(3) 0.203(10) Uani 0.50 1 d PU . . H3C H 0.2014 0.1970 0.7212 0.305 Uiso 0.50 1 d PR . . H3D H 0.1752 0.2500 0.8132 0.305 Uiso 1 2 d SR . . 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 Cu1 0.0446(6) 0.0306(5) 0.0426(5) 0.000 0.0155(4) 0.000 N1 0.060(3) 0.038(2) 0.032(2) -0.0022(16) 0.0094(18) -0.0117(19) N2 0.072(3) 0.071(3) 0.041(3) 0.002(2) -0.001(2) -0.036(3) N3 0.047(2) 0.0325(19) 0.036(2) 0.0018(16) 0.0069(18) -0.0059(17) N4 0.077(3) 0.044(2) 0.032(2) 0.0056(18) 0.016(2) 0.017(2) N5 0.092(4) 0.070(3) 0.045(3) 0.008(2) 0.008(3) 0.040(3) N6 0.055(3) 0.036(2) 0.034(2) 0.0016(17) 0.0118(18) 0.0037(18) Cl1 0.0504(11) 0.0575(11) 0.0313(8) 0.000 0.0026(7) 0.000 Cl2 0.0574(12) 0.0634(12) 0.0309(9) 0.000 0.0015(7) 0.000 C1 0.050(3) 0.042(2) 0.033(2) -0.006(2) 0.006(2) -0.010(2) C2 0.075(4) 0.063(4) 0.033(3) 0.002(2) 0.000(3) -0.024(3) C3 0.067(4) 0.038(3) 0.039(3) -0.001(2) 0.014(2) -0.007(2) C4 0.055(3) 0.044(3) 0.028(2) 0.0009(19) 0.014(2) -0.003(2) C5 0.056(3) 0.039(2) 0.029(2) 0.0009(19) 0.000(2) -0.003(2) C6 0.069(4) 0.042(3) 0.026(2) -0.0002(19) 0.001(2) -0.005(2) C7 0.070(4) 0.049(3) 0.034(3) 0.001(2) 0.020(3) 0.012(3) C8 0.045(3) 0.086(5) 0.046(3) 0.003(3) 0.009(2) 0.017(3) C9 0.049(3) 0.066(4) 0.046(3) -0.006(3) 0.010(2) -0.010(3) C10 0.093(5) 0.047(3) 0.047(3) 0.008(2) 0.031(3) 0.022(3) C11 0.060(3) 0.039(2) 0.033(2) 0.003(2) 0.007(2) 0.007(2) C12 0.087(5) 0.067(4) 0.033(3) 0.006(2) 0.009(3) 0.029(4) F1 0.056(2) 0.101(3) 0.098(3) -0.015(3) -0.004(2) -0.024(2) F2 0.056(2) 0.120(4) 0.116(4) 0.014(3) -0.001(2) 0.036(3) F3 0.103(3) 0.0475(18) 0.0482(19) -0.0015(15) -0.0166(19) -0.0171(18) F4 0.072(2) 0.0529(19) 0.063(2) 0.0119(16) -0.0242(18) -0.0024(17) O1 0.097(5) 0.164(7) 0.105(5) 0.031(5) 0.061(4) 0.073(4) O2 0.156(16) 0.33(3) 0.51(5) 0.000 0.10(2) 0.000 O3 0.198(10) 0.201(11) 0.210(11) -0.002(5) -0.008(5) 0.020(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 N6 2.016(4) 4_656 ? Cu1 N6 2.016(4) 5_656 ? Cu1 N3 2.020(4) 8_565 ? Cu1 N3 2.020(4) . ? Cu1 Cl2 2.767(2) . ? Cu1 Cl1 2.842(2) . ? N1 C1 1.319(6) . ? N1 N2 1.345(6) . ? N1 C3 1.459(6) . ? N2 C2 1.317(7) . ? N3 C1 1.324(6) . ? N3 C2 1.332(7) . ? N4 C11 1.326(7) . ? N4 N5 1.349(7) . ? N4 C10 1.450(7) . ? N5 C12 1.305(8) . ? N6 C11 1.313(6) . ? N6 C12 1.349(8) . ? N6 Cu1 2.016(4) 5_656 ? C1 H1 0.9300 . ? C2 H2 0.9300 . ? C3 C4 1.508(7) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 C9 1.361(9) . ? C4 C5 1.375(7) . ? C5 F4 1.325(6) . ? C5 C6 1.370(7) . ? C6 F3 1.332(6) . ? C6 C7 1.362(8) . ? C7 C8 1.384(10) . ? C7 C10 1.500(7) . ? C8 F2 1.351(7) . ? C8 C9 1.370(10) . ? C9 F1 1.328(7) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 H11 0.9300 . ? C12 H12 0.9300 . ? O1 H1A 0.8199 . ? O1 H1B 0.8199 . ? O2 H2A 0.8200 . ? O3 O3 1.22(4) 8_565 ? O3 H3C 0.8199 . ? O3 H3D 0.8900 . ? 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 N6 Cu1 N6 88.9(2) 4_656 5_656 ? N6 Cu1 N3 91.36(17) 4_656 8_565 ? N6 Cu1 N3 179.11(18) 5_656 8_565 ? N6 Cu1 N3 179.11(18) 4_656 . ? N6 Cu1 N3 91.36(17) 5_656 . ? N3 Cu1 N3 88.4(2) 8_565 . ? N6 Cu1 Cl2 88.83(14) 4_656 . ? N6 Cu1 Cl2 88.83(14) 5_656 . ? N3 Cu1 Cl2 92.02(13) 8_565 . ? N3 Cu1 Cl2 92.02(13) . . ? N6 Cu1 Cl1 90.51(14) 4_656 . ? N6 Cu1 Cl1 90.51(14) 5_656 . ? N3 Cu1 Cl1 88.64(13) 8_565 . ? N3 Cu1 Cl1 88.64(13) . . ? Cl2 Cu1 Cl1 179.08(6) . . ? C1 N1 N2 110.7(4) . . ? C1 N1 C3 128.9(5) . . ? N2 N1 C3 120.5(4) . . ? C2 N2 N1 101.9(4) . . ? C1 N3 C2 103.3(4) . . ? C1 N3 Cu1 128.6(3) . . ? C2 N3 Cu1 127.3(4) . . ? C11 N4 N5 110.3(4) . . ? C11 N4 C10 128.2(5) . . ? N5 N4 C10 121.0(5) . . ? C12 N5 N4 101.8(5) . . ? C11 N6 C12 102.4(4) . . ? C11 N6 Cu1 128.8(4) . 5_656 ? C12 N6 Cu1 127.6(4) . 5_656 ? N1 C1 N3 109.3(4) . . ? N1 C1 H1 125.4 . . ? N3 C1 H1 125.4 . . ? N2 C2 N3 114.8(5) . . ? N2 C2 H2 122.6 . . ? N3 C2 H2 122.6 . . ? N1 C3 C4 109.6(4) . . ? N1 C3 H3A 109.8 . . ? C4 C3 H3A 109.8 . . ? N1 C3 H3B 109.8 . . ? C4 C3 H3B 109.8 . . ? H3A C3 H3B 108.2 . . ? C9 C4 C5 116.6(5) . . ? C9 C4 C3 121.3(5) . . ? C5 C4 C3 122.1(5) . . ? F4 C5 C6 119.6(5) . . ? F4 C5 C4 118.5(5) . . ? C6 C5 C4 121.9(5) . . ? F3 C6 C7 120.1(5) . . ? F3 C6 C5 118.0(5) . . ? C7 C6 C5 121.9(5) . . ? C6 C7 C8 116.1(5) . . ? C6 C7 C10 121.1(6) . . ? C8 C7 C10 122.8(6) . . ? F2 C8 C9 119.7(7) . . ? F2 C8 C7 118.2(7) . . ? C9 C8 C7 122.0(6) . . ? F1 C9 C4 119.4(6) . . ? F1 C9 C8 119.0(6) . . ? C4 C9 C8 121.6(6) . . ? N4 C10 C7 111.3(5) . . ? N4 C10 H10A 109.4 . . ? C7 C10 H10A 109.4 . . ? N4 C10 H10B 109.4 . . ? C7 C10 H10B 109.4 . . ? H10A C10 H10B 108.0 . . ? N6 C11 N4 110.0(5) . . ? N6 C11 H11 125.0 . . ? N4 C11 H11 125.0 . . ? N5 C12 N6 115.5(5) . . ? N5 C12 H12 122.3 . . ? N6 C12 H12 122.3 . . ? H1A O1 H1B 121.4 . . ? O3 O3 H3C 140.8 8_565 . ? O3 O3 H3D 46.7 8_565 . ? H3C O3 H3D 125.0 . . ? 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 C1 N1 N2 C2 -0.5(7) . . . . ? C3 N1 N2 C2 178.5(6) . . . . ? N6 Cu1 N3 C1 6(12) 4_656 . . . ? N6 Cu1 N3 C1 111.2(5) 5_656 . . . ? N3 Cu1 N3 C1 -67.9(5) 8_565 . . . ? Cl2 Cu1 N3 C1 -159.9(5) . . . . ? Cl1 Cu1 N3 C1 20.7(5) . . . . ? N6 Cu1 N3 C2 174(100) 4_656 . . . ? N6 Cu1 N3 C2 -80.0(5) 5_656 . . . ? N3 Cu1 N3 C2 100.9(5) 8_565 . . . ? Cl2 Cu1 N3 C2 8.9(5) . . . . ? Cl1 Cu1 N3 C2 -170.4(5) . . . . ? C11 N4 N5 C12 -0.8(8) . . . . ? C10 N4 N5 C12 -173.3(6) . . . . ? N2 N1 C1 N3 0.6(6) . . . . ? C3 N1 C1 N3 -178.4(5) . . . . ? C2 N3 C1 N1 -0.4(6) . . . . ? Cu1 N3 C1 N1 170.5(3) . . . . ? N1 N2 C2 N3 0.3(8) . . . . ? C1 N3 C2 N2 0.0(8) . . . . ? Cu1 N3 C2 N2 -171.0(5) . . . . ? C1 N1 C3 C4 -115.3(6) . . . . ? N2 N1 C3 C4 65.8(7) . . . . ? N1 C3 C4 C9 88.4(6) . . . . ? N1 C3 C4 C5 -92.2(6) . . . . ? C9 C4 C5 F4 177.4(5) . . . . ? C3 C4 C5 F4 -1.9(7) . . . . ? C9 C4 C5 C6 -2.5(7) . . . . ? C3 C4 C5 C6 178.1(5) . . . . ? F4 C5 C6 F3 0.7(7) . . . . ? C4 C5 C6 F3 -179.4(4) . . . . ? F4 C5 C6 C7 -178.9(5) . . . . ? C4 C5 C6 C7 1.0(8) . . . . ? F3 C6 C7 C8 -178.7(5) . . . . ? C5 C6 C7 C8 0.9(8) . . . . ? F3 C6 C7 C10 0.3(8) . . . . ? C5 C6 C7 C10 179.9(5) . . . . ? C6 C7 C8 F2 176.3(5) . . . . ? C10 C7 C8 F2 -2.6(8) . . . . ? C6 C7 C8 C9 -1.4(8) . . . . ? C10 C7 C8 C9 179.7(5) . . . . ? C5 C4 C9 F1 -177.9(5) . . . . ? C3 C4 C9 F1 1.5(8) . . . . ? C5 C4 C9 C8 2.1(8) . . . . ? C3 C4 C9 C8 -178.5(5) . . . . ? F2 C8 C9 F1 2.2(8) . . . . ? C7 C8 C9 F1 179.8(5) . . . . ? F2 C8 C9 C4 -177.8(5) . . . . ? C7 C8 C9 C4 -0.2(9) . . . . ? C11 N4 C10 C7 135.0(6) . . . . ? N5 N4 C10 C7 -54.0(9) . . . . ? C6 C7 C10 N4 94.4(7) . . . . ? C8 C7 C10 N4 -86.7(7) . . . . ? C12 N6 C11 N4 0.2(7) . . . . ? Cu1 N6 C11 N4 -168.2(4) 5_656 . . . ? N5 N4 C11 N6 0.4(7) . . . . ? C10 N4 C11 N6 172.2(6) . . . . ? N4 N5 C12 N6 1.0(9) . . . . ? C11 N6 C12 N5 -0.8(8) . . . . ? Cu1 N6 C12 N5 167.8(5) 5_656 . . . ? 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 # #D H A D - H H...A D...A D - H...A symm(A) # O1 H1B O1 0.82 2.49 2.859(9) 109 5_676 yes O3 H3D Cl1 0.89 2.69 3.27(2) 124 3_456 yes C1 H1 Cl1 0.93 2.78 3.370(6) 123 . yes C2 H2 Cl2 0.93 2.79 3.397(6) 124 . yes C11 H11 Cl1 0.93 2.75 3.570(6) 147 4_647 yes C12 H12 Cl1 0.93 2.83 3.397(6) 121 4_646 yes _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 27.89 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 1.744 _refine_diff_density_min -0.770 _refine_diff_density_rms 0.268 _database_code_depnum_ccdc_archive 'CCDC 949177' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_6 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H20 Cu2 F4 N6 O8' _chemical_formula_weight 675.50 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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 18.9047(16) _cell_length_b 13.9019(12) _cell_length_c 22.304(2) _cell_angle_alpha 90.00 _cell_angle_beta 102.198(2) _cell_angle_gamma 90.00 _cell_volume 5729.5(9) _cell_formula_units_Z 8 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 5773 _cell_measurement_theta_min 2.45 _cell_measurement_theta_max 27.22 _exptl_crystal_description block _exptl_crystal_colour blue _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.566 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2720 _exptl_absorpt_coefficient_mu 1.562 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7056 _exptl_absorpt_correction_T_max 0.7882 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 16920 _diffrn_reflns_av_R_equivalents 0.0318 _diffrn_reflns_av_sigmaI/netI 0.0378 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_h_max 23 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 1.83 _diffrn_reflns_theta_max 26.00 _reflns_number_total 5620 _reflns_number_gt 4429 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0632P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5620 _refine_ls_number_parameters 365 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0482 _refine_ls_R_factor_gt 0.0355 _refine_ls_wR_factor_ref 0.1039 _refine_ls_wR_factor_gt 0.0972 _refine_ls_goodness_of_fit_ref 1.025 _refine_ls_restrained_S_all 1.025 _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 Cu1 Cu 0.160318(18) 0.52041(2) 0.202236(15) 0.03637(11) Uani 1 1 d . . . Cu2 Cu 0.184503(18) 0.63942(2) 0.297679(15) 0.03768(11) Uani 1 1 d . . . N1 N 0.10277(12) 0.27285(15) 0.09041(10) 0.0374(5) Uani 1 1 d . . . N2 N 0.07319(18) 0.33596(19) 0.04641(12) 0.0612(8) Uani 1 1 d . . . N3 N 0.13227(13) 0.41190(16) 0.13045(11) 0.0410(5) Uani 1 1 d . . . N4 N -0.19042(12) -0.25166(16) 0.13200(11) 0.0391(5) Uani 1 1 d . . . N5 N -0.17203(16) -0.17205(18) 0.04961(11) 0.0509(7) Uani 1 1 d . . . N6 N -0.18087(12) -0.10966(16) 0.09457(10) 0.0365(5) Uani 1 1 d . . . O1 O 0.12155(13) 0.55947(17) 0.33436(10) 0.0558(6) Uani 1 1 d . . . O2 O 0.10414(12) 0.45436(15) 0.25724(11) 0.0528(5) Uani 1 1 d . . . O3 O 0.26631(11) 0.54736(16) 0.32866(10) 0.0517(5) Uani 1 1 d . . . O4 O 0.24726(11) 0.45478(15) 0.24534(9) 0.0460(5) Uani 1 1 d . . . O5 O 0.24968(11) 0.70682(15) 0.25485(10) 0.0484(5) Uani 1 1 d . . . O6 O 0.22535(12) 0.61469(15) 0.17168(10) 0.0510(5) Uani 1 1 d . . . O7 O 0.10076(11) 0.70395(15) 0.24196(10) 0.0487(5) Uani 1 1 d . . . O8 O 0.07849(12) 0.59911(15) 0.16502(10) 0.0522(5) Uani 1 1 d . . . C1 C 0.0930(2) 0.4186(2) 0.07276(15) 0.0561(9) Uani 1 1 d . . . H1 H 0.0809 0.4772 0.0532 0.067 Uiso 1 1 calc R . . C2 C 0.13674(15) 0.3189(2) 0.13943(13) 0.0407(6) Uani 1 1 d . . . H2 H 0.1607 0.2895 0.1755 0.049 Uiso 1 1 calc R . . C3 C 0.09767(16) 0.1689(2) 0.07859(15) 0.0448(7) Uani 1 1 d . . . H3A H 0.1338 0.1363 0.1092 0.054 Uiso 1 1 calc R . . H3B H 0.1086 0.1563 0.0388 0.054 Uiso 1 1 calc R . . C4 C 0.02420(16) 0.12767(18) 0.07983(13) 0.0377(6) Uani 1 1 d . . . C5 C 0.00433(17) 0.1041(2) 0.13385(13) 0.0438(7) Uani 1 1 d . . . C6 C -0.06071(18) 0.0592(2) 0.13540(14) 0.0475(7) Uani 1 1 d . . . C7 C -0.11039(16) 0.03732(19) 0.08235(13) 0.0389(6) Uani 1 1 d . . . C8 C -0.09102(16) 0.06144(19) 0.02828(12) 0.0398(6) Uani 1 1 d . . . C9 C -0.02559(16) 0.10550(19) 0.02765(12) 0.0396(6) Uani 1 1 d . . . C10 C -0.18359(17) -0.0056(2) 0.08389(16) 0.0470(7) Uani 1 1 d . . . H10A H -0.2026 0.0255 0.1161 0.056 Uiso 1 1 calc R . . H10B H -0.2166 0.0076 0.0452 0.056 Uiso 1 1 calc R . . C11 C -0.19099(15) -0.1582(2) 0.14281(13) 0.0400(6) Uani 1 1 d . . . H11A H -0.1976 -0.1306 0.1792 0.048 Uiso 1 1 calc R . . C12 C -0.17835(18) -0.2555(2) 0.07431(14) 0.0488(7) Uani 1 1 d . . . H12 H -0.1749 -0.3131 0.0540 0.059 Uiso 1 1 calc R . . C13 C 0.09616(17) 0.4829(2) 0.30904(16) 0.0489(8) Uani 1 1 d . . . C14 C 0.0534(2) 0.4213(3) 0.3433(2) 0.0713(11) Uani 1 1 d . . . H14A H 0.0857 0.3821 0.3722 0.107 Uiso 1 1 calc R . . H14B H 0.0214 0.3809 0.3149 0.107 Uiso 1 1 calc R . . H14C H 0.0256 0.4615 0.3647 0.107 Uiso 1 1 calc R . . C15 C 0.28241(15) 0.4788(2) 0.29683(14) 0.0401(6) Uani 1 1 d . . . C16 C 0.34805(19) 0.4208(2) 0.32346(17) 0.0623(10) Uani 1 1 d . . . H16A H 0.3560 0.4221 0.3674 0.094 Uiso 1 1 calc R . . H16B H 0.3894 0.4474 0.3107 0.094 Uiso 1 1 calc R . . H16C H 0.3410 0.3555 0.3094 0.094 Uiso 1 1 calc R . . C17 C 0.25741(16) 0.6831(2) 0.20252(14) 0.0413(7) Uani 1 1 d . . . C18 C 0.3102(2) 0.7417(3) 0.1755(2) 0.0692(11) Uani 1 1 d . . . H18A H 0.2961 0.7405 0.1315 0.104 Uiso 1 1 calc R . . H18B H 0.3579 0.7150 0.1880 0.104 Uiso 1 1 calc R . . H18C H 0.3103 0.8069 0.1897 0.104 Uiso 1 1 calc R . . C19 C 0.06634(15) 0.6760(2) 0.19068(14) 0.0423(7) Uani 1 1 d . . . C20 C 0.00617(17) 0.7375(2) 0.15683(17) 0.0576(9) Uani 1 1 d . . . H20A H 0.0010 0.7931 0.1811 0.086 Uiso 1 1 calc R . . H20B H -0.0381 0.7013 0.1491 0.086 Uiso 1 1 calc R . . H20C H 0.0170 0.7575 0.1186 0.086 Uiso 1 1 calc R . . F1 F 0.04979(12) 0.12462(17) 0.18750(8) 0.0718(6) Uani 1 1 d . . . F2 F -0.07587(13) 0.03695(17) 0.18994(9) 0.0753(6) Uani 1 1 d . . . F3 F -0.01054(11) 0.12559(14) -0.02778(8) 0.0614(5) Uani 1 1 d . . . F4 F -0.13585(11) 0.04207(15) -0.02516(8) 0.0672(6) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.0370(2) 0.03066(19) 0.0412(2) -0.00624(14) 0.00763(14) -0.00269(14) Cu2 0.0408(2) 0.03294(19) 0.0416(2) -0.00673(14) 0.01390(15) 0.00350(14) N1 0.0439(13) 0.0286(11) 0.0397(13) -0.0020(10) 0.0086(10) -0.0060(10) N2 0.094(2) 0.0380(14) 0.0421(15) -0.0002(12) -0.0072(14) -0.0033(15) N3 0.0421(13) 0.0328(13) 0.0459(14) -0.0037(11) 0.0044(11) -0.0037(10) N4 0.0438(13) 0.0360(13) 0.0393(13) 0.0035(10) 0.0129(10) -0.0053(10) N5 0.0808(19) 0.0399(14) 0.0371(13) 0.0003(11) 0.0240(13) -0.0008(13) N6 0.0441(13) 0.0310(12) 0.0377(12) 0.0012(10) 0.0158(10) -0.0043(10) O1 0.0678(15) 0.0510(14) 0.0576(13) 0.0024(11) 0.0336(12) 0.0033(11) O2 0.0529(13) 0.0437(12) 0.0666(15) 0.0027(11) 0.0233(11) -0.0083(10) O3 0.0517(13) 0.0492(12) 0.0500(12) -0.0140(10) 0.0011(10) 0.0140(10) O4 0.0414(11) 0.0450(11) 0.0487(12) -0.0118(10) 0.0027(9) 0.0095(9) O5 0.0510(12) 0.0431(11) 0.0550(13) -0.0119(10) 0.0203(10) -0.0101(10) O6 0.0585(13) 0.0437(12) 0.0570(13) -0.0116(10) 0.0262(11) -0.0157(10) O7 0.0469(12) 0.0449(12) 0.0536(13) -0.0022(10) 0.0086(10) 0.0082(10) O8 0.0486(12) 0.0430(12) 0.0597(13) -0.0032(11) -0.0006(10) 0.0028(10) C1 0.078(2) 0.0339(16) 0.0504(18) 0.0024(14) -0.0003(17) -0.0035(15) C2 0.0406(15) 0.0440(17) 0.0367(15) 0.0002(13) 0.0063(12) -0.0025(13) C3 0.0532(18) 0.0292(14) 0.0546(18) -0.0057(13) 0.0172(14) -0.0042(13) C4 0.0534(17) 0.0233(13) 0.0385(15) -0.0027(11) 0.0148(13) -0.0059(12) C5 0.0589(19) 0.0413(16) 0.0317(14) -0.0023(12) 0.0105(13) -0.0061(14) C6 0.064(2) 0.0434(17) 0.0390(16) 0.0039(13) 0.0209(15) -0.0024(15) C7 0.0504(17) 0.0273(13) 0.0432(16) -0.0001(12) 0.0194(13) -0.0023(12) C8 0.0539(17) 0.0334(15) 0.0324(14) -0.0016(12) 0.0100(13) -0.0062(13) C9 0.0543(18) 0.0322(14) 0.0353(15) 0.0028(12) 0.0163(13) -0.0033(13) C10 0.0505(18) 0.0321(15) 0.0618(19) 0.0031(14) 0.0196(15) -0.0003(13) C11 0.0431(16) 0.0409(16) 0.0387(15) 0.0011(12) 0.0145(12) -0.0048(13) C12 0.071(2) 0.0354(16) 0.0418(16) -0.0044(13) 0.0164(15) -0.0049(15) C13 0.0424(17) 0.0451(19) 0.064(2) 0.0179(16) 0.0228(15) 0.0154(14) C14 0.059(2) 0.060(2) 0.105(3) 0.035(2) 0.040(2) 0.0107(18) C15 0.0383(15) 0.0337(15) 0.0483(17) -0.0045(13) 0.0093(13) 0.0012(12) C16 0.060(2) 0.051(2) 0.067(2) -0.0127(17) -0.0069(17) 0.0180(17) C17 0.0446(16) 0.0313(15) 0.0524(18) -0.0042(13) 0.0200(14) -0.0003(12) C18 0.078(3) 0.053(2) 0.091(3) -0.0100(19) 0.049(2) -0.0214(19) C19 0.0336(15) 0.0438(17) 0.0515(18) 0.0123(14) 0.0132(13) -0.0036(13) C20 0.0391(17) 0.055(2) 0.076(2) 0.0235(18) 0.0057(16) 0.0006(15) F1 0.0742(14) 0.0963(16) 0.0403(10) -0.0061(10) 0.0012(9) -0.0237(12) F2 0.0936(15) 0.0963(16) 0.0418(10) 0.0091(10) 0.0272(10) -0.0243(13) F3 0.0801(13) 0.0686(12) 0.0392(9) 0.0045(9) 0.0212(9) -0.0219(10) F4 0.0739(13) 0.0775(13) 0.0456(10) -0.0015(10) 0.0022(9) -0.0271(11) _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 Cu1 O8 1.933(2) . ? Cu1 O4 1.9470(19) . ? Cu1 O2 2.007(2) . ? Cu1 O6 2.012(2) . ? Cu1 N3 2.182(2) . ? Cu1 Cu2 2.6583(5) . ? Cu2 O1 1.932(2) . ? Cu2 O5 1.951(2) . ? Cu2 O7 2.006(2) . ? Cu2 O3 2.014(2) . ? Cu2 N4 2.166(2) 2_565 ? N1 C2 1.312(4) . ? N1 N2 1.347(3) . ? N1 C3 1.469(3) . ? N2 C1 1.308(4) . ? N3 C2 1.309(4) . ? N3 C1 1.346(4) . ? N4 C11 1.323(4) . ? N4 C12 1.355(4) . ? N4 Cu2 2.166(2) 2_545 ? N5 C12 1.300(4) . ? N5 N6 1.363(3) . ? N6 C11 1.318(3) . ? N6 C10 1.465(3) . ? O1 C13 1.252(4) . ? O2 C13 1.261(4) . ? O3 C15 1.263(3) . ? O4 C15 1.245(3) . ? O5 C17 1.251(3) . ? O6 C17 1.252(3) . ? O7 C19 1.252(4) . ? O8 C19 1.257(4) . ? C1 H1 0.9300 . ? C2 H2 0.9300 . ? C3 C4 1.508(4) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 C9 1.368(4) . ? C4 C5 1.375(4) . ? C5 F1 1.348(3) . ? C5 C6 1.386(4) . ? C6 F2 1.344(3) . ? C6 C7 1.380(4) . ? C7 C8 1.374(4) . ? C7 C10 1.514(4) . ? C8 F4 1.336(3) . ? C8 C9 1.383(4) . ? C9 F3 1.355(3) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 H11A 0.9300 . ? C12 H12 0.9300 . ? C13 C14 1.494(4) . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 0.9600 . ? C15 C16 1.494(4) . ? C16 H16A 0.9600 . ? C16 H16B 0.9600 . ? C16 H16C 0.9600 . ? C17 C18 1.510(4) . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? C19 C20 1.493(4) . ? C20 H20A 0.9600 . ? C20 H20B 0.9600 . ? C20 H20C 0.9600 . ? 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 O8 Cu1 O4 173.13(9) . . ? O8 Cu1 O2 92.44(10) . . ? O4 Cu1 O2 89.10(9) . . ? O8 Cu1 O6 88.66(10) . . ? O4 Cu1 O6 87.71(10) . . ? O2 Cu1 O6 160.98(9) . . ? O8 Cu1 N3 91.59(9) . . ? O4 Cu1 N3 95.01(9) . . ? O2 Cu1 N3 93.12(9) . . ? O6 Cu1 N3 105.84(9) . . ? O8 Cu1 Cu2 88.75(7) . . ? O4 Cu1 Cu2 84.94(6) . . ? O2 Cu1 Cu2 79.57(7) . . ? O6 Cu1 Cu2 81.47(6) . . ? N3 Cu1 Cu2 172.68(7) . . ? O1 Cu2 O5 173.20(9) . . ? O1 Cu2 O7 92.49(10) . . ? O5 Cu2 O7 88.81(9) . . ? O1 Cu2 O3 89.21(10) . . ? O5 Cu2 O3 87.39(10) . . ? O7 Cu2 O3 160.93(8) . . ? O1 Cu2 N4 92.16(9) . 2_565 ? O5 Cu2 N4 94.44(9) . 2_565 ? O7 Cu2 N4 92.82(9) . 2_565 ? O3 Cu2 N4 106.10(8) . 2_565 ? O1 Cu2 Cu1 87.94(7) . . ? O5 Cu2 Cu1 85.78(6) . . ? O7 Cu2 Cu1 78.61(6) . . ? O3 Cu2 Cu1 82.47(6) . . ? N4 Cu2 Cu1 171.42(6) 2_565 . ? C2 N1 N2 110.2(2) . . ? C2 N1 C3 129.2(3) . . ? N2 N1 C3 120.6(2) . . ? C1 N2 N1 102.1(2) . . ? C2 N3 C1 102.6(2) . . ? C2 N3 Cu1 124.96(19) . . ? C1 N3 Cu1 130.8(2) . . ? C11 N4 C12 102.8(2) . . ? C11 N4 Cu2 123.80(19) . 2_545 ? C12 N4 Cu2 131.9(2) . 2_545 ? C12 N5 N6 102.7(2) . . ? C11 N6 N5 109.7(2) . . ? C11 N6 C10 129.2(2) . . ? N5 N6 C10 121.0(2) . . ? C13 O1 Cu2 120.6(2) . . ? C13 O2 Cu1 126.7(2) . . ? C15 O3 Cu2 123.03(19) . . ? C15 O4 Cu1 124.05(18) . . ? C17 O5 Cu2 122.72(18) . . ? C17 O6 Cu1 124.61(19) . . ? C19 O7 Cu2 128.1(2) . . ? C19 O8 Cu1 119.5(2) . . ? N2 C1 N3 114.6(3) . . ? N2 C1 H1 122.7 . . ? N3 C1 H1 122.7 . . ? N3 C2 N1 110.5(3) . . ? N3 C2 H2 124.8 . . ? N1 C2 H2 124.8 . . ? N1 C3 C4 113.3(2) . . ? N1 C3 H3A 108.9 . . ? C4 C3 H3A 108.9 . . ? N1 C3 H3B 108.9 . . ? C4 C3 H3B 108.9 . . ? H3A C3 H3B 107.7 . . ? C9 C4 C5 115.2(3) . . ? C9 C4 C3 122.7(3) . . ? C5 C4 C3 122.0(3) . . ? F1 C5 C4 119.1(3) . . ? F1 C5 C6 118.4(3) . . ? C4 C5 C6 122.5(3) . . ? F2 C6 C7 119.3(3) . . ? F2 C6 C5 119.1(3) . . ? C7 C6 C5 121.6(3) . . ? C8 C7 C6 116.1(3) . . ? C8 C7 C10 122.0(3) . . ? C6 C7 C10 121.8(3) . . ? F4 C8 C7 119.8(3) . . ? F4 C8 C9 118.7(2) . . ? C7 C8 C9 121.5(3) . . ? F3 C9 C4 119.4(3) . . ? F3 C9 C8 117.5(2) . . ? C4 C9 C8 123.2(3) . . ? N6 C10 C7 113.1(2) . . ? N6 C10 H10A 109.0 . . ? C7 C10 H10A 109.0 . . ? N6 C10 H10B 109.0 . . ? C7 C10 H10B 109.0 . . ? H10A C10 H10B 107.8 . . ? N6 C11 N4 110.2(3) . . ? N6 C11 H11A 124.9 . . ? N4 C11 H11A 124.9 . . ? N5 C12 N4 114.6(3) . . ? N5 C12 H12 122.7 . . ? N4 C12 H12 122.7 . . ? O1 C13 O2 124.9(3) . . ? O1 C13 C14 117.0(3) . . ? O2 C13 C14 118.1(3) . . ? C13 C14 H14A 109.5 . . ? C13 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C13 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? O4 C15 O3 125.2(3) . . ? O4 C15 C16 117.3(3) . . ? O3 C15 C16 117.5(3) . . ? C15 C16 H16A 109.5 . . ? C15 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C15 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? O5 C17 O6 125.1(3) . . ? O5 C17 C18 116.6(3) . . ? O6 C17 C18 118.3(3) . . ? C17 C18 H18A 109.5 . . ? C17 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C17 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? O7 C19 O8 124.8(3) . . ? O7 C19 C20 118.5(3) . . ? O8 C19 C20 116.7(3) . . ? C19 C20 H20A 109.5 . . ? C19 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C19 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 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 O8 Cu1 Cu2 O1 89.89(10) . . . . ? O4 Cu1 Cu2 O1 -92.85(10) . . . . ? O2 Cu1 Cu2 O1 -2.83(9) . . . . ? O6 Cu1 Cu2 O1 178.72(9) . . . . ? N3 Cu1 Cu2 O1 -2.9(5) . . . . ? O8 Cu1 Cu2 O5 -92.71(9) . . . . ? O4 Cu1 Cu2 O5 84.56(9) . . . . ? O2 Cu1 Cu2 O5 174.57(9) . . . . ? O6 Cu1 Cu2 O5 -3.88(9) . . . . ? N3 Cu1 Cu2 O5 174.5(5) . . . . ? O8 Cu1 Cu2 O7 -3.08(9) . . . . ? O4 Cu1 Cu2 O7 174.19(9) . . . . ? O2 Cu1 Cu2 O7 -95.79(9) . . . . ? O6 Cu1 Cu2 O7 85.75(9) . . . . ? N3 Cu1 Cu2 O7 -95.9(5) . . . . ? O8 Cu1 Cu2 O3 179.37(10) . . . . ? O4 Cu1 Cu2 O3 -3.37(9) . . . . ? O2 Cu1 Cu2 O3 86.65(10) . . . . ? O6 Cu1 Cu2 O3 -91.80(10) . . . . ? N3 Cu1 Cu2 O3 86.6(5) . . . . ? O8 Cu1 Cu2 N4 -0.9(4) . . . 2_565 ? O4 Cu1 Cu2 N4 176.3(4) . . . 2_565 ? O2 Cu1 Cu2 N4 -93.6(4) . . . 2_565 ? O6 Cu1 Cu2 N4 87.9(4) . . . 2_565 ? N3 Cu1 Cu2 N4 -93.7(7) . . . 2_565 ? C2 N1 N2 C1 0.8(4) . . . . ? C3 N1 N2 C1 -176.1(3) . . . . ? O8 Cu1 N3 C2 -140.2(2) . . . . ? O4 Cu1 N3 C2 41.7(2) . . . . ? O2 Cu1 N3 C2 -47.6(2) . . . . ? O6 Cu1 N3 C2 130.8(2) . . . . ? Cu2 Cu1 N3 C2 -47.6(6) . . . . ? O8 Cu1 N3 C1 22.8(3) . . . . ? O4 Cu1 N3 C1 -155.3(3) . . . . ? O2 Cu1 N3 C1 115.4(3) . . . . ? O6 Cu1 N3 C1 -66.2(3) . . . . ? Cu2 Cu1 N3 C1 115.4(5) . . . . ? C12 N5 N6 C11 0.6(3) . . . . ? C12 N5 N6 C10 -175.0(3) . . . . ? O5 Cu2 O1 C13 -17.5(10) . . . . ? O7 Cu2 O1 C13 83.4(2) . . . . ? O3 Cu2 O1 C13 -77.6(2) . . . . ? N4 Cu2 O1 C13 176.3(2) 2_565 . . . ? Cu1 Cu2 O1 C13 4.9(2) . . . . ? O8 Cu1 O2 C13 -86.4(3) . . . . ? O4 Cu1 O2 C13 86.9(3) . . . . ? O6 Cu1 O2 C13 6.6(4) . . . . ? N3 Cu1 O2 C13 -178.1(3) . . . . ? Cu2 Cu1 O2 C13 1.9(2) . . . . ? O1 Cu2 O3 C15 93.7(2) . . . . ? O5 Cu2 O3 C15 -80.4(2) . . . . ? O7 Cu2 O3 C15 -1.6(4) . . . . ? N4 Cu2 O3 C15 -174.2(2) 2_565 . . . ? Cu1 Cu2 O3 C15 5.7(2) . . . . ? O8 Cu1 O4 C15 25.9(9) . . . . ? O2 Cu1 O4 C15 -77.2(2) . . . . ? O6 Cu1 O4 C15 84.1(2) . . . . ? N3 Cu1 O4 C15 -170.2(2) . . . . ? Cu2 Cu1 O4 C15 2.4(2) . . . . ? O1 Cu2 O5 C17 26.0(9) . . . . ? O7 Cu2 O5 C17 -75.1(2) . . . . ? O3 Cu2 O5 C17 86.2(2) . . . . ? N4 Cu2 O5 C17 -167.8(2) 2_565 . . . ? Cu1 Cu2 O5 C17 3.6(2) . . . . ? O8 Cu1 O6 C17 94.9(2) . . . . ? O4 Cu1 O6 C17 -79.3(2) . . . . ? O2 Cu1 O6 C17 1.3(4) . . . . ? N3 Cu1 O6 C17 -173.8(2) . . . . ? Cu2 Cu1 O6 C17 5.9(2) . . . . ? O1 Cu2 O7 C19 -85.2(2) . . . . ? O5 Cu2 O7 C19 88.1(2) . . . . ? O3 Cu2 O7 C19 9.6(4) . . . . ? N4 Cu2 O7 C19 -177.5(2) 2_565 . . . ? Cu1 Cu2 O7 C19 2.2(2) . . . . ? O4 Cu1 O8 C19 -18.3(9) . . . . ? O2 Cu1 O8 C19 84.6(2) . . . . ? O6 Cu1 O8 C19 -76.4(2) . . . . ? N3 Cu1 O8 C19 177.8(2) . . . . ? Cu2 Cu1 O8 C19 5.1(2) . . . . ? N1 N2 C1 N3 -0.7(4) . . . . ? C2 N3 C1 N2 0.3(4) . . . . ? Cu1 N3 C1 N2 -165.5(2) . . . . ? C1 N3 C2 N1 0.3(3) . . . . ? Cu1 N3 C2 N1 167.17(18) . . . . ? N2 N1 C2 N3 -0.7(3) . . . . ? C3 N1 C2 N3 175.8(3) . . . . ? C2 N1 C3 C4 107.2(3) . . . . ? N2 N1 C3 C4 -76.6(4) . . . . ? N1 C3 C4 C9 102.5(3) . . . . ? N1 C3 C4 C5 -81.7(3) . . . . ? C9 C4 C5 F1 -179.1(3) . . . . ? C3 C4 C5 F1 4.8(4) . . . . ? C9 C4 C5 C6 1.3(4) . . . . ? C3 C4 C5 C6 -174.8(3) . . . . ? F1 C5 C6 F2 -0.7(5) . . . . ? C4 C5 C6 F2 178.9(3) . . . . ? F1 C5 C6 C7 179.0(3) . . . . ? C4 C5 C6 C7 -1.4(5) . . . . ? F2 C6 C7 C8 -179.5(3) . . . . ? C5 C6 C7 C8 0.8(4) . . . . ? F2 C6 C7 C10 3.8(4) . . . . ? C5 C6 C7 C10 -175.8(3) . . . . ? C6 C7 C8 F4 179.5(3) . . . . ? C10 C7 C8 F4 -3.8(4) . . . . ? C6 C7 C8 C9 -0.3(4) . . . . ? C10 C7 C8 C9 176.4(3) . . . . ? C5 C4 C9 F3 -179.6(3) . . . . ? C3 C4 C9 F3 -3.5(4) . . . . ? C5 C4 C9 C8 -0.8(4) . . . . ? C3 C4 C9 C8 175.3(3) . . . . ? F4 C8 C9 F3 -0.7(4) . . . . ? C7 C8 C9 F3 179.2(3) . . . . ? F4 C8 C9 C4 -179.5(3) . . . . ? C7 C8 C9 C4 0.3(5) . . . . ? C11 N6 C10 C7 111.7(3) . . . . ? N5 N6 C10 C7 -73.6(4) . . . . ? C8 C7 C10 N6 102.5(3) . . . . ? C6 C7 C10 N6 -81.0(4) . . . . ? N5 N6 C11 N4 -0.9(3) . . . . ? C10 N6 C11 N4 174.2(3) . . . . ? C12 N4 C11 N6 0.7(3) . . . . ? Cu2 N4 C11 N6 167.95(18) 2_545 . . . ? N6 N5 C12 N4 -0.2(4) . . . . ? C11 N4 C12 N5 -0.3(4) . . . . ? Cu2 N4 C12 N5 -166.0(2) 2_545 . . . ? Cu2 O1 C13 O2 -5.2(4) . . . . ? Cu2 O1 C13 C14 174.7(2) . . . . ? Cu1 O2 C13 O1 1.3(5) . . . . ? Cu1 O2 C13 C14 -178.6(2) . . . . ? Cu1 O4 C15 O3 1.3(4) . . . . ? Cu1 O4 C15 C16 -179.9(2) . . . . ? Cu2 O3 C15 O4 -6.0(4) . . . . ? Cu2 O3 C15 C16 175.1(2) . . . . ? Cu2 O5 C17 O6 -0.2(4) . . . . ? Cu2 O5 C17 C18 -179.6(2) . . . . ? Cu1 O6 C17 O5 -5.4(4) . . . . ? Cu1 O6 C17 C18 174.0(2) . . . . ? Cu2 O7 C19 O8 1.1(4) . . . . ? Cu2 O7 C19 C20 -179.0(2) . . . . ? Cu1 O8 C19 O7 -5.2(4) . . . . ? Cu1 O8 C19 C20 174.9(2) . . . . ? # SQUEEZE RESULTS (APPEND TO CIF) # Note: Data are Listed for all Voids in the P1 Unit Cell # i.e. Centre of Gravity, Solvent Accessible Volume, # Recovered number of Electrons in the Void and # Details about the Squeezed Material loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons _platon_squeeze_void_content 1 0.250 -0.250 0.000 188 38 ' ' 2 0.250 0.250 0.500 188 38 ' ' 3 0.750 -0.250 0.500 188 38 ' ' 4 0.750 0.250 1.000 188 38 ' ' _platon_squeeze_details ; ; 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 # #D H A D - H H...A D...A D - H...A symm(A) # C2 H2 O5 0.9300 2.3400 3.234(4) 160.00 4_545 yes C3 H3A O3 0.9700 2.4300 3.391(4) 170.00 4_545 yes C3 H3B N5 0.9700 2.5200 3.443(4) 158.00 5_555 yes C10 H10A O6 0.9700 2.3800 3.319(4) 164.00 3_445 yes C11 H11A O4 0.9300 2.3100 3.192(4) 159.00 3_445 yes C16 H16A F4 0.9600 2.4200 3.365(4) 168.00 8_556 yes C20 H20B O1 0.9600 2.6000 3.492(4) 155.00 2_555 yes _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.343 _refine_diff_density_min -0.291 _refine_diff_density_rms 0.064 _database_code_depnum_ccdc_archive 'CCDC 949178'