# 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_compound-1 #TrackingRef '16069_web_deposit_cif_file_0_OscarCastillo_1355215083.CIFs.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; Poly[[(mu-pyrazine)copper(I)] perchlorate heptahydrate] ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C8 H8 Cu N4, Cl O4, 7(H2 O)' _chemical_formula_sum 'C8 H22 Cl Cu N4 O11' _chemical_formula_weight 493.03 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Trigonal _symmetry_space_group_name_H-M P3112 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z+1/3' '-x+y, -x, z+2/3' '-y, -x, -z+2/3' 'x, x-y, -z' '-x+y, y, -z+1/3' _cell_length_a 10.8055(15) _cell_length_b 10.8055(15) _cell_length_c 12.637(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 1277.8(4) _cell_formula_units_Z 3 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 1588 _cell_measurement_theta_min 2.18 _cell_measurement_theta_max 26.49 _exptl_crystal_description prismatic _exptl_crystal_colour red _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.752 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 696 _exptl_absorpt_coefficient_mu 1.502 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.1568 _exptl_absorpt_correction_T_max 0.2018 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 1588 _diffrn_reflns_av_R_equivalents 0.0683 _diffrn_reflns_av_sigmaI/netI 0.1358 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.18 _diffrn_reflns_theta_max 26.49 _reflns_number_total 1588 _reflns_number_gt 750 _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. ; # 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 -0.018 -0.011 0.005 730 366 ' ' _platon_squeeze_details ; ; _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^)+(0.0567P)^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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.08(4) _refine_ls_number_reflns 1588 _refine_ls_number_parameters 60 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0993 _refine_ls_R_factor_gt 0.0461 _refine_ls_wR_factor_ref 0.1110 _refine_ls_wR_factor_gt 0.1026 _refine_ls_goodness_of_fit_ref 0.778 _refine_ls_restrained_S_all 0.778 _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 0.99773(9) 0.49887(5) 0.5000 0.0755(4) Uani 1 2 d S . . N1 N 1.1474(6) 0.4953(6) 0.5980(3) 0.0736(12) Uani 1 1 d . . . N2 N 0.8712(5) 0.3430(5) 0.4015(3) 0.0792(15) Uani 1 1 d . . . C1 C 1.2481(6) 0.5989(6) 0.6313(4) 0.0672(17) Uani 1 1 d . . . H1 H 1.2613 0.6870 0.6097 0.081 Uiso 1 1 calc R . . C2 C 1.1327(9) 0.3586(6) 0.6340(4) 0.105(3) Uani 1 1 d . . . H2 H 1.0569 0.2726 0.6102 0.127 Uiso 1 1 calc R . . C4 C 0.7531(7) 0.2206(7) 0.4377(4) 0.087(2) Uani 1 1 d . . . H4 H 0.7390 0.2025 0.5099 0.104 Uiso 1 1 calc R . . C3 C 0.8689(7) 0.3384(9) 0.2962(5) 0.114(3) Uani 1 1 d . . . H3 H 0.9469 0.4160 0.2647 0.137 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.0595(7) 0.0952(7) 0.0599(5) -0.0049(5) 0.000 0.0297(3) N1 0.091(4) 0.076(3) 0.073(3) -0.004(4) 0.008(3) 0.056(4) N2 0.088(4) 0.068(4) 0.038(2) 0.000(2) -0.010(2) 0.007(3) C1 0.056(4) 0.038(3) 0.107(5) -0.002(3) -0.039(3) 0.024(3) C2 0.177(10) 0.048(4) 0.073(5) 0.038(3) 0.026(4) 0.042(4) C4 0.096(5) 0.087(5) 0.050(3) 0.000(3) -0.002(3) 0.025(4) C3 0.076(5) 0.152(7) 0.092(5) 0.029(5) 0.023(4) 0.040(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 N2 1.988(4) . ? Cu1 N2 1.988(4) 5_556 ? Cu1 N1 2.053(4) . ? Cu1 N1 2.053(4) 5_556 ? N1 C1 1.182(6) . ? N1 C2 1.476(6) . ? N2 C3 1.332(7) . ? N2 C4 1.378(6) . ? C1 C1 1.426(9) 6_756 ? C1 H1 0.9300 . ? C2 C2 1.301(14) 6_756 ? C2 H2 0.9300 . ? C4 C3 1.295(8) 4_665 ? C4 H4 0.9300 . ? C3 C4 1.295(8) 4_665 ? C3 H3 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 N2 Cu1 N2 106.9(3) . 5_556 ? N2 Cu1 N1 125.2(2) . . ? N2 Cu1 N1 103.69(16) 5_556 . ? N2 Cu1 N1 103.69(16) . 5_556 ? N2 Cu1 N1 125.2(2) 5_556 5_556 ? N1 Cu1 N1 93.9(3) . 5_556 ? C1 N1 C2 115.2(5) . . ? C1 N1 Cu1 123.9(4) . . ? C2 N1 Cu1 120.9(5) . . ? C3 N2 C4 107.7(4) . . ? C3 N2 Cu1 130.5(5) . . ? C4 N2 Cu1 121.3(3) . . ? N1 C1 C1 124.8(3) . 6_756 ? N1 C1 H1 117.6 . . ? C1 C1 H1 117.6 6_756 . ? C2 C2 N1 120.0(4) 6_756 . ? C2 C2 H2 120.0 6_756 . ? N1 C2 H2 120.0 . . ? C3 C4 N2 119.6(5) 4_665 . ? C3 C4 H4 120.2 4_665 . ? N2 C4 H4 120.2 . . ? C4 C3 N2 132.6(6) 4_665 . ? C4 C3 H3 113.7 4_665 . ? N2 C3 H3 113.7 . . ? _diffrn_measured_fraction_theta_max 0.923 _diffrn_reflns_theta_full 26.49 _diffrn_measured_fraction_theta_full 0.923 _refine_diff_density_max 0.265 _refine_diff_density_min -0.347 _refine_diff_density_rms 0.050 _database_code_depnum_ccdc_archive 'CCDC 915205' ####################################################################### # # 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_compound-2 #TrackingRef '16069_web_deposit_cif_file_0_OscarCastillo_1355215083.CIFs.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; Poly[[tetrakis(mu-pyrazine-KN:KN')dicopper(I)] diperchlorate-benzoic acid-water (1/1/1)] ; _chemical_formula_moiety '2(C16 H16 Cu2 N8), 3(C7 H6 O2), 4(Cl1 O4), H2 O' _chemical_formula_sum 'C53 H52 Cl4 Cu4 N16 O23' _chemical_formula_weight 1677.08 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu -1.9646 0.5888 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/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 10.837(3) _cell_length_b 18.131(4) _cell_length_c 17.561(5) _cell_angle_alpha 90.00 _cell_angle_beta 104.301(18) _cell_angle_gamma 90.00 _cell_volume 3343.4(15) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 17241 _cell_measurement_theta_min 3.56 _cell_measurement_theta_max 69.43 _exptl_crystal_description prismatic _exptl_crystal_colour colourless _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.06 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.667 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1700 _exptl_absorpt_coefficient_mu 3.673 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.681 _exptl_absorpt_correction_T_max 0.740 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\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 17241 _diffrn_reflns_av_R_equivalents 0.0425 _diffrn_reflns_av_sigmaI/netI 0.0423 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 3.56 _diffrn_reflns_theta_max 69.43 _reflns_number_total 6026 _reflns_number_gt 4725 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Sir92 (Altamore et al., 1993)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 (Farrugia, 1997)' _computing_publication_material 'WinGX (Farrugia, 1999)' _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^)+(0.0712P)^2^+3.9932P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6026 _refine_ls_number_parameters 524 _refine_ls_number_restraints 6 _refine_ls_R_factor_all 0.0635 _refine_ls_R_factor_gt 0.0479 _refine_ls_wR_factor_ref 0.1347 _refine_ls_wR_factor_gt 0.1217 _refine_ls_goodness_of_fit_ref 1.030 _refine_ls_restrained_S_all 1.030 _refine_ls_shift/su_max 0.005 _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 0.95558(5) 0.14045(3) 0.62506(3) 0.02621(15) Uani 1 1 d . . . Cu2 Cu 0.55272(5) 0.13269(3) 0.86997(3) 0.02525(15) Uani 1 1 d . . . N1 N 0.8457(3) 0.11399(16) 0.70282(16) 0.0254(6) Uani 1 1 d . . . N2 N 0.6782(3) 0.11334(16) 0.80299(16) 0.0243(6) Uani 1 1 d . . . C1 C 0.7223(4) 0.0964(2) 0.6775(2) 0.0314(8) Uani 1 1 d . . . H1 H 0.6901 0.0837 0.6238 0.038 Uiso 1 1 calc R . . C2 C 0.6397(3) 0.0961(2) 0.7261(2) 0.0303(8) Uani 1 1 d . . . H2 H 0.5530 0.0832 0.7047 0.036 Uiso 1 1 calc R . . C3 C 0.8035(3) 0.12852(19) 0.8291(2) 0.0252(7) Uani 1 1 d . . . H3 H 0.8366 0.1391 0.8833 0.030 Uiso 1 1 calc R . . C4 C 0.8856(3) 0.12924(19) 0.7801(2) 0.0263(7) Uani 1 1 d . . . H4 H 0.9728 0.1408 0.8016 0.032 Uiso 1 1 calc R . . N3 N 1.1339(3) 0.15082(16) 0.69451(16) 0.0245(6) Uani 1 1 d . . . N4 N 1.3777(3) 0.14672(16) 0.79713(16) 0.0234(6) Uani 1 1 d . . . C5 C 1.1783(3) 0.0905(2) 0.7366(2) 0.0297(8) Uani 1 1 d . . . H5 H 1.1258 0.0479 0.7313 0.036 Uiso 1 1 calc R . . C6 C 1.2978(3) 0.0884(2) 0.7875(2) 0.0296(8) Uani 1 1 d . . . H6 H 1.3246 0.0446 0.8167 0.036 Uiso 1 1 calc R . . C7 C 1.3335(4) 0.2062(2) 0.7542(2) 0.0300(8) Uani 1 1 d . . . H7 H 1.3866 0.2484 0.7581 0.036 Uiso 1 1 calc R . . C8 C 1.2122(4) 0.2084(2) 0.7038(2) 0.0306(8) Uani 1 1 d . . . H8 H 1.1845 0.2523 0.6753 0.037 Uiso 1 1 calc R . . N5 N 0.9823(3) 0.05348(16) 0.55336(17) 0.0264(6) Uani 1 1 d . . . C9 C 1.0742(6) 0.0571(3) 0.5175(4) 0.076(2) Uani 1 1 d . . . H9 H 1.1319 0.0974 0.5286 0.091 Uiso 1 1 calc R . . C10 C 0.9094(5) -0.0044(3) 0.5362(4) 0.0649(17) Uani 1 1 d . . . H10 H 0.8422 -0.0107 0.5616 0.078 Uiso 1 1 calc R . . N6 N 0.8384(3) 0.20841(16) 0.55122(16) 0.0242(6) Uani 1 1 d . . . N7 N 0.6546(3) 0.29429(16) 0.44902(16) 0.0246(6) Uani 1 1 d . . . C11 C 0.7847(4) 0.2672(2) 0.5761(2) 0.0379(9) Uani 1 1 d . . . H11 H 0.8090 0.2799 0.6302 0.045 Uiso 1 1 calc R . . C12 C 0.6948(4) 0.3100(2) 0.5254(2) 0.0359(9) Uani 1 1 d . . . H12 H 0.6607 0.3518 0.5456 0.043 Uiso 1 1 calc R . . C13 C 0.7073(4) 0.2346(2) 0.4248(2) 0.0309(8) Uani 1 1 d . . . H13 H 0.6814 0.2209 0.3710 0.037 Uiso 1 1 calc R . . C14 C 0.7978(4) 0.1926(2) 0.4750(2) 0.0283(7) Uani 1 1 d . . . H14 H 0.8324 0.1510 0.4547 0.034 Uiso 1 1 calc R . . N8 N 0.5189(3) 0.05018(16) 0.94356(16) 0.0235(6) Uani 1 1 d . . . C15 C 0.5909(3) -0.01072(19) 0.96112(19) 0.0239(7) Uani 1 1 d . . . H15 H 0.6558 -0.0199 0.9346 0.029 Uiso 1 1 calc R . . C16 C 0.5721(3) -0.06050(19) 1.0174(2) 0.0255(7) Uani 1 1 d . . . H16 H 0.6250 -0.1029 1.0286 0.031 Uiso 1 1 calc R . . C17 C 0.0876(4) 0.0713(2) 0.1846(2) 0.0310(8) Uani 1 1 d . . . C18 C -0.0015(4) 0.0980(2) 0.2235(3) 0.0383(9) Uani 1 1 d . . . H18 H -0.0901 0.0935 0.1999 0.046 Uiso 1 1 calc R . . C19 C 0.0401(4) 0.1314(3) 0.2969(3) 0.0483(11) Uani 1 1 d . . . H19 H -0.0201 0.1503 0.3231 0.058 Uiso 1 1 calc R . . C20 C 0.1694(4) 0.1371(3) 0.3316(3) 0.0478(11) Uani 1 1 d . . . H20 H 0.1976 0.1599 0.3816 0.057 Uiso 1 1 calc R . . C21 C 0.2577(4) 0.1096(2) 0.2936(3) 0.0393(9) Uani 1 1 d . . . H21 H 0.3460 0.1129 0.3183 0.047 Uiso 1 1 calc R . . C22 C 0.2183(4) 0.0771(2) 0.2196(2) 0.0320(8) Uani 1 1 d . . . H22 H 0.2790 0.0591 0.1934 0.038 Uiso 1 1 calc R . . C23 C 0.0487(3) 0.0372(2) 0.1054(2) 0.0296(8) Uani 1 1 d . . . O1 O -0.0760(2) 0.03599(17) 0.07510(16) 0.0381(6) Uani 1 1 d . . . H1A H -0.0913 0.0225 0.0279 0.057 Uiso 1 1 calc R . . O2 O 0.1252(2) 0.01107(15) 0.07153(15) 0.0322(6) Uani 1 1 d . . . C24 C 0.498(6) -0.0114(14) 0.4938(16) 0.050(6) Uani 0.50 1 d PD A -1 C25 C 0.5245(9) 0.0547(6) 0.4611(5) 0.043(2) Uani 0.50 1 d PD A -1 H25 H 0.5774 0.0564 0.4254 0.052 Uiso 0.50 1 calc PR A -1 C26 C 0.4703(14) 0.1183(9) 0.4831(10) 0.072(6) Uani 0.50 1 d PD A -1 H26 H 0.4813 0.1637 0.4585 0.087 Uiso 0.50 1 calc PR A -1 C27 C 0.4005(11) 0.1177(7) 0.5400(6) 0.051(2) Uani 0.50 1 d PD A -1 H27 H 0.3658 0.1623 0.5539 0.061 Uiso 0.50 1 calc PR A -1 C28 C 0.381(2) 0.0525(7) 0.5764(12) 0.057(5) Uani 0.50 1 d PD A -1 H28 H 0.3359 0.0520 0.6163 0.068 Uiso 0.50 1 calc PR A -1 C29 C 0.4307(8) -0.0130(6) 0.5528(5) 0.0388(19) Uani 0.50 1 d PD A -1 H29 H 0.4186 -0.0585 0.5768 0.047 Uiso 0.50 1 calc PR A -1 C030 C 0.5515(9) -0.0796(8) 0.4670(5) 0.047(2) Uani 0.50 1 d P A -1 O3 O 0.5040(8) -0.1415(7) 0.4936(7) 0.057(3) Uani 0.50 1 d P A -1 H3A H 0.5311 -0.1790 0.4749 0.086 Uiso 0.50 1 calc PR A -1 O4 O 0.6206(15) -0.0839(8) 0.4222(9) 0.060(3) Uani 0.50 1 d P A -1 O5 O 0.4591(6) 0.2380(4) 0.0814(4) 0.0533(17) Uani 0.50 1 d P . . H5A H 0.5020 0.2196 0.1241 0.080 Uiso 0.50 1 d P . . H5B H 0.3811 0.2272 0.0703 0.080 Uiso 0.50 1 d P . . Cl1 Cl 0.62680(9) 0.10725(6) 0.24067(5) 0.0393(2) Uani 1 1 d . . . O6 O 0.5787(3) 0.1798(2) 0.23890(19) 0.0591(7) Uani 1 1 d . . . O7 O 0.5257(3) 0.0542(3) 0.2438(2) 0.0760(13) Uani 1 1 d . . . O8 O 0.6670(3) 0.09147(15) 0.17085(15) 0.0361(6) Uani 1 1 d . . . O9 O 0.7290(3) 0.0950(2) 0.30862(19) 0.0591(7) Uani 1 1 d . . . Cl2 Cl 0.12631(9) 0.19990(5) 0.98286(5) 0.0347(2) Uani 1 1 d . . . O10 O 0.2270(4) 0.1748(2) 1.0507(2) 0.0493(10) Uani 0.775(3) 1 d P B 1 O11 O 0.0103(4) 0.1639(2) 0.9894(3) 0.0527(11) Uani 0.775(3) 1 d P B 1 O12 O 0.1607(5) 0.1809(3) 0.9133(3) 0.0554(12) Uani 0.775(3) 1 d P B 1 O13 O 0.1128(4) 0.2781(2) 0.9897(3) 0.0497(11) Uani 0.775(3) 1 d P B 1 O14 O 0.0281(12) 0.2500(7) 0.9306(7) 0.037(3) Uani 0.225(3) 1 d P B 2 O15 O 0.1289(18) 0.1343(10) 0.9349(8) 0.057(5) Uani 0.225(3) 1 d P B 2 O16 O 0.0899(19) 0.1842(11) 1.0493(11) 0.075(4) Uani 0.225(3) 1 d P B 2 O17 O 0.2373(19) 0.2396(10) 0.9938(10) 0.075(4) Uani 0.225(3) 1 d P B 2 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 0.0242(3) 0.0318(3) 0.0211(3) -0.00134(19) 0.0028(2) 0.0054(2) Cu2 0.0225(3) 0.0302(3) 0.0221(3) 0.00190(19) 0.0037(2) -0.0052(2) N1 0.0270(14) 0.0290(15) 0.0195(14) 0.0010(11) 0.0042(12) 0.0002(12) N2 0.0247(14) 0.0247(15) 0.0224(14) 0.0015(11) 0.0039(11) -0.0007(11) C1 0.0298(18) 0.043(2) 0.0192(17) -0.0041(14) 0.0009(14) -0.0048(16) C2 0.0251(17) 0.037(2) 0.0267(18) -0.0045(15) 0.0029(15) -0.0072(15) C3 0.0238(16) 0.0304(18) 0.0191(16) 0.0007(13) 0.0011(14) 0.0027(14) C4 0.0229(16) 0.0299(18) 0.0250(17) 0.0002(13) 0.0040(14) 0.0009(14) N3 0.0236(14) 0.0285(15) 0.0210(14) 0.0007(11) 0.0046(12) 0.0018(11) N4 0.0209(13) 0.0261(15) 0.0230(14) -0.0001(11) 0.0051(11) -0.0005(11) C5 0.0262(17) 0.0256(18) 0.0348(19) 0.0026(14) 0.0028(15) -0.0044(14) C6 0.0284(18) 0.0244(18) 0.0317(19) 0.0068(14) -0.0006(15) -0.0036(14) C7 0.0309(18) 0.0236(18) 0.0336(19) 0.0039(14) 0.0044(15) -0.0038(14) C8 0.0300(18) 0.0261(18) 0.0321(19) 0.0052(14) 0.0009(15) 0.0000(15) N5 0.0247(14) 0.0298(16) 0.0242(14) -0.0019(11) 0.0053(12) 0.0038(12) C9 0.076(4) 0.051(3) 0.129(5) -0.052(3) 0.082(4) -0.038(3) C10 0.079(4) 0.040(3) 0.102(4) -0.030(3) 0.073(4) -0.027(2) N6 0.0251(14) 0.0262(15) 0.0203(14) -0.0021(11) 0.0038(11) 0.0006(12) N7 0.0252(14) 0.0267(15) 0.0212(14) 0.0010(11) 0.0046(12) 0.0002(12) C11 0.048(2) 0.039(2) 0.0217(18) -0.0084(15) -0.0012(17) 0.0136(18) C12 0.042(2) 0.038(2) 0.0256(19) -0.0054(15) 0.0040(17) 0.0144(17) C13 0.039(2) 0.0274(19) 0.0228(17) -0.0035(14) 0.0008(15) 0.0019(15) C14 0.0360(19) 0.0258(18) 0.0217(17) -0.0018(13) 0.0046(15) 0.0048(15) N8 0.0238(14) 0.0245(15) 0.0220(14) 0.0003(11) 0.0055(12) -0.0033(11) C15 0.0218(15) 0.0281(17) 0.0228(16) -0.0010(13) 0.0076(13) 0.0003(13) C16 0.0232(16) 0.0247(17) 0.0295(18) 0.0004(13) 0.0083(14) 0.0020(13) C17 0.0319(18) 0.0239(18) 0.041(2) 0.0060(15) 0.0172(17) 0.0017(15) C18 0.0309(19) 0.038(2) 0.050(2) 0.0008(18) 0.0190(18) 0.0020(17) C19 0.042(2) 0.052(3) 0.059(3) -0.014(2) 0.026(2) 0.001(2) C20 0.043(2) 0.048(3) 0.057(3) -0.019(2) 0.022(2) -0.006(2) C21 0.035(2) 0.037(2) 0.048(2) -0.0039(18) 0.0144(19) -0.0038(17) C22 0.0317(18) 0.0271(18) 0.042(2) 0.0024(15) 0.0173(17) 0.0037(15) C23 0.0280(18) 0.0257(18) 0.038(2) 0.0102(14) 0.0139(16) 0.0040(14) O1 0.0273(13) 0.0517(17) 0.0383(15) 0.0022(13) 0.0137(12) 0.0063(12) O2 0.0274(12) 0.0368(14) 0.0350(14) 0.0060(11) 0.0128(11) 0.0071(11) C24 0.034(5) 0.080(16) 0.028(8) -0.002(11) -0.008(9) -0.022(16) C25 0.041(5) 0.050(6) 0.031(5) 0.012(4) -0.004(4) -0.020(5) C26 0.044(7) 0.106(16) 0.056(10) 0.021(9) -0.010(6) -0.029(8) C27 0.034(5) 0.070(8) 0.040(6) 0.003(5) -0.005(5) -0.005(6) C28 0.043(7) 0.086(13) 0.033(6) 0.011(8) -0.004(5) -0.004(9) C29 0.031(4) 0.052(6) 0.030(4) 0.001(4) 0.002(4) -0.011(4) C030 0.024(4) 0.084(8) 0.030(5) 0.003(5) -0.001(4) 0.005(5) O3 0.035(5) 0.071(6) 0.068(7) 0.018(5) 0.018(5) -0.003(5) O4 0.030(4) 0.096(10) 0.054(6) 0.033(8) 0.011(4) -0.005(7) O5 0.027(3) 0.076(5) 0.054(4) 0.018(3) 0.004(3) 0.006(3) Cl1 0.0293(4) 0.0607(6) 0.0267(5) -0.0078(4) 0.0045(4) 0.0133(4) O6 0.0604(15) 0.0662(16) 0.0402(12) -0.0133(11) -0.0074(11) 0.0243(13) O7 0.0421(19) 0.132(4) 0.058(2) -0.001(2) 0.0200(17) -0.022(2) O8 0.0448(16) 0.0361(15) 0.0294(14) 0.0002(11) 0.0133(12) 0.0006(12) O9 0.0604(15) 0.0662(16) 0.0402(12) -0.0133(11) -0.0074(11) 0.0243(13) Cl2 0.0371(5) 0.0321(5) 0.0321(5) -0.0001(3) 0.0030(4) -0.0016(4) O10 0.047(2) 0.053(2) 0.036(2) 0.0038(17) -0.0110(18) -0.0002(19) O11 0.039(2) 0.047(2) 0.064(3) 0.010(2) -0.003(2) -0.0096(18) O12 0.065(3) 0.065(3) 0.033(2) -0.008(2) 0.005(2) 0.015(3) O13 0.063(3) 0.034(2) 0.057(3) 0.0051(18) 0.025(2) 0.0042(19) O14 0.045(7) 0.044(7) 0.028(6) 0.004(5) 0.019(6) 0.009(6) O15 0.071(11) 0.061(11) 0.029(7) -0.001(7) -0.006(7) 0.045(9) O16 0.084(9) 0.067(8) 0.070(8) 0.016(6) 0.011(7) -0.017(7) O17 0.084(9) 0.067(8) 0.070(8) 0.016(6) 0.011(7) -0.017(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 N6 2.000(3) . ? Cu1 N3 2.023(3) . ? Cu1 N1 2.078(3) . ? Cu1 N5 2.082(3) . ? Cu2 N4 2.024(3) 1_455 ? Cu2 N7 2.035(3) 4_566 ? Cu2 N2 2.036(3) . ? Cu2 N8 2.068(3) . ? N1 C1 1.339(5) . ? N1 C4 1.348(4) . ? N2 C2 1.348(5) . ? N2 C3 1.350(5) . ? C1 C2 1.381(5) . ? C1 H1 0.9500 . ? C2 H2 0.9500 . ? C3 C4 1.382(5) . ? C3 H3 0.9500 . ? C4 H4 0.9500 . ? N3 C8 1.329(5) . ? N3 C5 1.340(5) . ? N4 C7 1.335(5) . ? N4 C6 1.351(5) . ? N4 Cu2 2.024(3) 1_655 ? C5 C6 1.381(5) . ? C5 H5 0.9500 . ? C6 H6 0.9500 . ? C7 C8 1.391(5) . ? C7 H7 0.9500 . ? C8 H8 0.9500 . ? N5 C10 1.303(6) . ? N5 C9 1.305(6) . ? C9 C10 1.385(6) 3_756 ? C9 H9 0.9500 . ? C10 C9 1.385(6) 3_756 ? C10 H10 0.9500 . ? N6 C14 1.333(4) . ? N6 C11 1.338(5) . ? N7 C12 1.335(5) . ? N7 C13 1.341(5) . ? N7 Cu2 2.035(3) 4_565 ? C11 C12 1.384(5) . ? C11 H11 0.9500 . ? C12 H12 0.9500 . ? C13 C14 1.376(5) . ? C13 H13 0.9500 . ? C14 H14 0.9500 . ? N8 C15 1.343(5) . ? N8 C16 1.346(5) 3_657 ? C15 C16 1.390(5) . ? C15 H15 0.9500 . ? C16 N8 1.346(5) 3_657 ? C16 H16 0.9500 . ? C17 C18 1.400(5) . ? C17 C22 1.401(5) . ? C17 C23 1.486(6) . ? C18 C19 1.395(6) . ? C18 H18 0.9500 . ? C19 C20 1.387(7) . ? C19 H19 0.9500 . ? C20 C21 1.387(6) . ? C20 H20 0.9500 . ? C21 C22 1.394(6) . ? C21 H21 0.9500 . ? C22 H22 0.9500 . ? C23 O2 1.228(5) . ? C23 O1 1.324(5) . ? O1 H1A 0.8400 . ? C24 C25 1.390(10) . ? C24 C29 1.41(5) . ? C24 C030 1.49(5) . ? C25 C26 1.391(10) . ? C25 H25 0.9500 . ? C26 C27 1.395(10) . ? C26 H26 0.9500 . ? C27 C28 1.383(10) . ? C27 H27 0.9500 . ? C28 C29 1.406(10) . ? C28 H28 0.9500 . ? C29 H29 0.9500 . ? C030 O4 1.215(16) . ? C030 O3 1.365(16) . ? O3 H3A 0.8400 . ? O5 H5A 0.8470 . ? O5 H5B 0.8426 . ? Cl1 O6 1.412(4) . ? Cl1 O8 1.428(3) . ? Cl1 O9 1.430(3) . ? Cl1 O7 1.469(4) . ? Cl2 O16 1.351(18) . ? Cl2 O17 1.374(18) . ? Cl2 O12 1.405(4) . ? Cl2 O13 1.433(4) . ? Cl2 O11 1.447(4) . ? Cl2 O15 1.461(15) . ? Cl2 O10 1.475(4) . ? Cl2 O14 1.522(12) . ? 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 N3 133.83(12) . . ? N6 Cu1 N1 101.13(12) . . ? N3 Cu1 N1 104.05(12) . . ? N6 Cu1 N5 103.61(12) . . ? N3 Cu1 N5 100.38(12) . . ? N1 Cu1 N5 114.24(12) . . ? N4 Cu2 N7 127.94(12) 1_455 4_566 ? N4 Cu2 N2 108.16(12) 1_455 . ? N7 Cu2 N2 100.31(12) 4_566 . ? N4 Cu2 N8 101.70(12) 1_455 . ? N7 Cu2 N8 101.21(11) 4_566 . ? N2 Cu2 N8 118.88(12) . . ? C1 N1 C4 115.4(3) . . ? C1 N1 Cu1 121.6(2) . . ? C4 N1 Cu1 121.4(2) . . ? C2 N2 C3 115.1(3) . . ? C2 N2 Cu2 122.2(2) . . ? C3 N2 Cu2 121.9(2) . . ? N1 C1 C2 122.9(3) . . ? N1 C1 H1 118.6 . . ? C2 C1 H1 118.6 . . ? N2 C2 C1 122.0(3) . . ? N2 C2 H2 119.0 . . ? C1 C2 H2 119.0 . . ? N2 C3 C4 122.6(3) . . ? N2 C3 H3 118.7 . . ? C4 C3 H3 118.7 . . ? N1 C4 C3 122.0(3) . . ? N1 C4 H4 119.0 . . ? C3 C4 H4 119.0 . . ? C8 N3 C5 116.2(3) . . ? C8 N3 Cu1 129.3(2) . . ? C5 N3 Cu1 114.5(2) . . ? C7 N4 C6 115.6(3) . . ? C7 N4 Cu2 127.4(2) . 1_655 ? C6 N4 Cu2 116.9(2) . 1_655 ? N3 C5 C6 122.1(3) . . ? N3 C5 H5 119.0 . . ? C6 C5 H5 119.0 . . ? N4 C6 C5 121.9(3) . . ? N4 C6 H6 119.0 . . ? C5 C6 H6 119.0 . . ? N4 C7 C8 122.2(3) . . ? N4 C7 H7 118.9 . . ? C8 C7 H7 118.9 . . ? N3 C8 C7 122.0(3) . . ? N3 C8 H8 119.0 . . ? C7 C8 H8 119.0 . . ? C10 N5 C9 114.9(4) . . ? C10 N5 Cu1 125.6(3) . . ? C9 N5 Cu1 119.4(3) . . ? N5 C9 C10 122.4(4) . 3_756 ? N5 C9 H9 118.8 . . ? C10 C9 H9 118.8 3_756 . ? N5 C10 C9 122.7(4) . 3_756 ? N5 C10 H10 118.6 . . ? C9 C10 H10 118.6 3_756 . ? C14 N6 C11 115.9(3) . . ? C14 N6 Cu1 121.2(2) . . ? C11 N6 Cu1 122.5(2) . . ? C12 N7 C13 115.6(3) . . ? C12 N7 Cu2 122.3(2) . 4_565 ? C13 N7 Cu2 120.7(2) . 4_565 ? N6 C11 C12 122.0(3) . . ? N6 C11 H11 119.0 . . ? C12 C11 H11 119.0 . . ? N7 C12 C11 122.0(3) . . ? N7 C12 H12 119.0 . . ? C11 C12 H12 119.0 . . ? N7 C13 C14 122.4(3) . . ? N7 C13 H13 118.8 . . ? C14 C13 H13 118.8 . . ? N6 C14 C13 122.1(3) . . ? N6 C14 H14 119.0 . . ? C13 C14 H14 119.0 . . ? C15 N8 C16 117.0(3) . 3_657 ? C15 N8 Cu2 123.8(2) . . ? C16 N8 Cu2 118.9(2) 3_657 . ? N8 C15 C16 121.2(3) . . ? N8 C15 H15 119.4 . . ? C16 C15 H15 119.4 . . ? N8 C16 C15 121.7(3) 3_657 . ? N8 C16 H16 119.1 3_657 . ? C15 C16 H16 119.1 . . ? C18 C17 C22 120.3(4) . . ? C18 C17 C23 122.0(4) . . ? C22 C17 C23 117.7(3) . . ? C19 C18 C17 119.8(4) . . ? C19 C18 H18 120.1 . . ? C17 C18 H18 120.1 . . ? C20 C19 C18 119.9(4) . . ? C20 C19 H19 120.0 . . ? C18 C19 H19 120.0 . . ? C21 C20 C19 120.3(4) . . ? C21 C20 H20 119.9 . . ? C19 C20 H20 119.9 . . ? C20 C21 C22 120.7(4) . . ? C20 C21 H21 119.6 . . ? C22 C21 H21 119.6 . . ? C21 C22 C17 119.0(4) . . ? C21 C22 H22 120.5 . . ? C17 C22 H22 120.5 . . ? O2 C23 O1 123.0(4) . . ? O2 C23 C17 122.9(3) . . ? O1 C23 C17 114.1(3) . . ? C23 O1 H1A 109.5 . . ? C25 C24 C29 121(3) . . ? C25 C24 C030 117(3) . . ? C29 C24 C030 122.0(12) . . ? C24 C25 C26 117(2) . . ? C24 C25 H25 121.4 . . ? C26 C25 H25 121.4 . . ? C25 C26 C27 122.1(16) . . ? C25 C26 H26 118.9 . . ? C27 C26 H26 118.9 . . ? C28 C27 C26 120.6(15) . . ? C28 C27 H27 119.7 . . ? C26 C27 H27 119.7 . . ? C27 C28 C29 118.2(15) . . ? C27 C28 H28 120.9 . . ? C29 C28 H28 120.9 . . ? C24 C29 C28 120.3(16) . . ? C24 C29 H29 119.9 . . ? C28 C29 H29 119.9 . . ? O4 C030 O3 120.9(15) . . ? O4 C030 C24 127.6(17) . . ? O3 C030 C24 111.2(15) . . ? H5A O5 H5B 114.4 . . ? O6 Cl1 O8 110.9(2) . . ? O6 Cl1 O9 111.6(2) . . ? O8 Cl1 O9 110.4(2) . . ? O6 Cl1 O7 109.6(3) . . ? O8 Cl1 O7 106.8(2) . . ? O9 Cl1 O7 107.3(2) . . ? O16 Cl2 O17 115.0(11) . . ? O12 Cl2 O13 111.7(3) . . ? O12 Cl2 O11 112.4(3) . . ? O13 Cl2 O11 109.3(3) . . ? O16 Cl2 O15 112.1(12) . . ? O17 Cl2 O15 111.4(12) . . ? O12 Cl2 O10 109.0(3) . . ? O13 Cl2 O10 107.9(3) . . ? O11 Cl2 O10 106.3(2) . . ? O16 Cl2 O14 109.7(10) . . ? O17 Cl2 O14 103.3(9) . . ? O15 Cl2 O14 104.4(7) . . ? 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 O1 H1A O2 0.84 1.80 2.639(4) 177.2 3 O3 H3A O5 0.84 1.82 2.633(14) 163.1 2_645 O5 H5A O6 0.85 2.11 2.945(7) 169.0 . O5 H5B O10 0.84 1.88 2.695(8) 163.0 1_554 O5 H5B O17 0.84 1.80 2.51(2) 141.0 1_554 _diffrn_measured_fraction_theta_max 0.962 _diffrn_reflns_theta_full 69.43 _diffrn_measured_fraction_theta_full 0.962 _refine_diff_density_max 1.365 _refine_diff_density_min -1.227 _refine_diff_density_rms 0.085 _database_code_depnum_ccdc_archive 'CCDC 915206' ####################################################################### # # 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_compound-3_100K #TrackingRef '16069_web_deposit_cif_file_0_OscarCastillo_1355215083.CIFs.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; catena-Poly[[bis(benzoato-K2O,O')bis(mu-benzoato-KO:KO')bis(mu-pyrazine-KN,KN') dicobalt(II)]-benzoic acid (1/1)] ; _chemical_formula_moiety 'C18 H14 Co N2 O4, 1/2(C7 H6 O2)' _chemical_formula_structural 'C18 H14 Co N2 O4, 1/2(C7 H6 O2)' _chemical_formula_sum 'C21.50 H17 Co N2 O5' _chemical_formula_weight 442.30 _chemical_compound_source 'synthesis as described' loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Co Co -2.3653 3.6143 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' _symmetry_Int_Tables_number 2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.1207(3) _cell_length_b 8.9131(4) _cell_length_c 15.6874(7) _cell_angle_alpha 95.278(3) _cell_angle_beta 94.010(3) _cell_angle_gamma 106.181(2) _cell_volume 947.38(7) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 8291 _cell_measurement_theta_min 2.84 _cell_measurement_theta_max 67.54 _exptl_crystal_description prismatic _exptl_crystal_colour red _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.04 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.551 _exptl_crystal_density_method ? _exptl_crystal_F_000 454 _exptl_absorpt_coefficient_mu 7.433 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type Xcalibur _diffrn_measurement_method \w _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 8291 _diffrn_reflns_av_R_equivalents 0.0435 _diffrn_reflns_av_sigmaI/netI 0.0495 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.84 _diffrn_reflns_theta_max 67.54 _reflns_number_total 3259 _reflns_number_gt 2713 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlis CCD (Oxford Diffraction, 2003)' _computing_cell_refinement 'CrysAlis CCD (Oxford Diffraction, 2003)' _computing_data_reduction 'CrysAlis RED (Oxford Diffraction, 2003)' _computing_structure_solution 'Sir92 (Altamore et al., 1993)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 (Farrugia, 1997)' _computing_publication_material 'WinGX (Farrugia, 1999)' _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^)+(0.0908P)^2^+1.4557P] 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 3259 _refine_ls_number_parameters 262 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0732 _refine_ls_R_factor_gt 0.0588 _refine_ls_wR_factor_ref 0.1580 _refine_ls_wR_factor_gt 0.1476 _refine_ls_goodness_of_fit_ref 1.040 _refine_ls_restrained_S_all 1.040 _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 0.61638(9) 0.67740(7) 0.92467(4) 0.0176(2) Uani 1 1 d . . . C1 C 0.6885(6) 0.8509(5) 0.8075(3) 0.0210(9) Uani 1 1 d . . . C2 C 0.7577(6) 0.9491(5) 0.7379(3) 0.0214(9) Uani 1 1 d . . . C3 C 0.8463(7) 1.1100(5) 0.7563(3) 0.0254(10) Uani 1 1 d . . . H3 H 0.8600 1.1589 0.8137 0.031 Uiso 1 1 calc R . . C4 C 0.9145(7) 1.1994(6) 0.6912(3) 0.0305(11) Uani 1 1 d . . . H4 H 0.9718 1.3097 0.7039 0.037 Uiso 1 1 calc R . . C5 C 0.8996(7) 1.1289(6) 0.6082(3) 0.0331(11) Uani 1 1 d . . . H5 H 0.9485 1.1906 0.5640 0.040 Uiso 1 1 calc R . . C6 C 0.8132(8) 0.9681(7) 0.5890(3) 0.0364(12) Uani 1 1 d . . . H6 H 0.8025 0.9192 0.5317 0.044 Uiso 1 1 calc R . . C7 C 0.7429(7) 0.8796(6) 0.6542(3) 0.0303(10) Uani 1 1 d . . . H7 H 0.6835 0.7696 0.6413 0.036 Uiso 1 1 calc R . . C8 C 0.4239(6) 0.3093(5) 0.8900(3) 0.0186(9) Uani 1 1 d . . . C9 C 0.3916(6) 0.2139(5) 0.8039(3) 0.0211(9) Uani 1 1 d . . . C10 C 0.2939(7) 0.0543(5) 0.7955(3) 0.0270(10) Uani 1 1 d . . . H10 H 0.2438 0.0065 0.8440 0.032 Uiso 1 1 calc R . . C11 C 0.2694(8) -0.0353(6) 0.7164(3) 0.0357(12) Uani 1 1 d . . . H11 H 0.2040 -0.1448 0.7109 0.043 Uiso 1 1 calc R . . C12 C 0.3403(8) 0.0346(7) 0.6456(3) 0.0381(13) Uani 1 1 d . . . H12 H 0.3245 -0.0274 0.5915 0.046 Uiso 1 1 calc R . . C13 C 0.4340(8) 0.1943(7) 0.6528(3) 0.0362(12) Uani 1 1 d . . . H13 H 0.4795 0.2419 0.6035 0.043 Uiso 1 1 calc R . . C14 C 0.4617(7) 0.2851(6) 0.7321(3) 0.0282(10) Uani 1 1 d . . . H14 H 0.5277 0.3945 0.7375 0.034 Uiso 1 1 calc R . . C15 C 0.9768(7) 0.5722(5) 0.8738(3) 0.0237(9) Uani 1 1 d . . . H15 H 0.8798 0.4947 0.8364 0.028 Uiso 1 1 calc R . . C16 C 1.0642(6) 0.7827(5) 0.9777(3) 0.0210(9) Uani 1 1 d . . . H16 H 1.0310 0.8586 1.0157 0.025 Uiso 1 1 calc R . . C17 C 0.2580(6) 0.7846(5) 0.9768(3) 0.0214(9) Uani 1 1 d . . . H17 H 0.3551 0.8622 1.0142 0.026 Uiso 1 1 calc R . . C18 C 0.1715(6) 0.5751(5) 0.8729(3) 0.0239(9) Uani 1 1 d . . . H18 H 0.2050 0.5002 0.8344 0.029 Uiso 1 1 calc R . . N1 N 0.9211(5) 0.6759(4) 0.9261(2) 0.0183(7) Uani 1 1 d . . . N2 N 0.3142(5) 0.6806(4) 0.9249(2) 0.0186(7) Uani 1 1 d . . . O1 O 0.6046(5) 0.7050(3) 0.78922(19) 0.0248(7) Uani 1 1 d . . . O2 O 0.7175(4) 0.9112(3) 0.88542(18) 0.0226(7) Uani 1 1 d . . . O3 O 0.5450(4) 0.4432(3) 0.89982(19) 0.0230(7) Uani 1 1 d . . . O4 O 0.3300(4) 0.2457(4) 0.94916(19) 0.0231(7) Uani 1 1 d . . . O91 O 0.2747(13) 0.5985(9) 0.6799(5) 0.061(2) Uiso 0.50 1 d PD A -1 H91 H 0.3886 0.6245 0.7129 0.091 Uiso 0.50 1 d P B -1 C91 C 0.3061(15) 0.5520(7) 0.6051(6) 0.047(3) Uiso 0.50 1 d PD A -1 O92 O 0.4612(14) 0.5340(10) 0.5828(6) 0.072(3) Uiso 0.50 1 d PD A -1 C92 C 0.1337(13) 0.5160(9) 0.5375(5) 0.043(3) Uiso 0.50 1 d PD A -1 C93 C 0.1659(14) 0.4661(10) 0.4541(5) 0.045(3) Uiso 0.50 1 d PD A -1 H93 H 0.2935 0.4593 0.4442 0.054 Uiso 0.50 1 calc PR A -1 C94 C 0.0244(14) 0.4266(11) 0.3862(6) 0.056(3) Uiso 0.50 1 d PD A -1 H94 H 0.0527 0.3910 0.3310 0.067 Uiso 0.50 1 calc PR A -1 C95 C -0.1581(14) 0.4391(12) 0.3989(6) 0.057(3) Uiso 0.50 1 d PD A -1 H95 H -0.2570 0.4133 0.3517 0.068 Uiso 0.50 1 calc PR A -1 C96 C -0.2036(15) 0.4905(13) 0.4821(7) 0.074(5) Uiso 0.50 1 d PD A -1 H96 H -0.3307 0.4994 0.4913 0.089 Uiso 0.50 1 calc PR A -1 C97 C -0.0500(12) 0.5275(11) 0.5503(6) 0.056(3) Uiso 0.50 1 d PD A -1 H97 H -0.0756 0.5613 0.6064 0.067 Uiso 0.50 1 calc PR A -1 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 0.0129(4) 0.0198(4) 0.0190(4) 0.0016(3) 0.0013(2) 0.0035(2) C1 0.015(2) 0.023(2) 0.026(2) 0.0054(18) 0.0025(17) 0.0060(17) C2 0.015(2) 0.027(2) 0.023(2) 0.0061(18) 0.0020(17) 0.0047(17) C3 0.021(2) 0.027(2) 0.027(2) 0.0015(19) -0.0023(18) 0.0072(18) C4 0.028(3) 0.028(2) 0.038(3) 0.015(2) 0.008(2) 0.008(2) C5 0.032(3) 0.042(3) 0.032(3) 0.018(2) 0.013(2) 0.014(2) C6 0.041(3) 0.048(3) 0.024(2) 0.006(2) 0.009(2) 0.015(2) C7 0.032(3) 0.031(2) 0.027(2) 0.003(2) 0.003(2) 0.008(2) C8 0.013(2) 0.025(2) 0.019(2) 0.0036(17) 0.0007(16) 0.0069(16) C9 0.015(2) 0.029(2) 0.021(2) 0.0010(18) 0.0010(16) 0.0086(17) C10 0.024(2) 0.030(2) 0.028(2) 0.001(2) -0.0007(19) 0.0094(19) C11 0.032(3) 0.033(3) 0.040(3) -0.010(2) -0.009(2) 0.013(2) C12 0.031(3) 0.054(3) 0.029(3) -0.015(2) -0.007(2) 0.020(2) C13 0.031(3) 0.063(4) 0.017(2) 0.002(2) 0.003(2) 0.017(2) C14 0.018(2) 0.041(3) 0.025(2) 0.003(2) 0.0021(18) 0.009(2) C15 0.019(2) 0.029(2) 0.022(2) 0.0004(18) 0.0008(17) 0.0070(18) C16 0.021(2) 0.019(2) 0.022(2) 0.0031(17) 0.0026(17) 0.0026(17) C17 0.020(2) 0.019(2) 0.024(2) 0.0031(18) -0.0006(18) 0.0059(17) C18 0.022(2) 0.027(2) 0.024(2) -0.0006(19) 0.0008(18) 0.0105(18) N1 0.0173(18) 0.0204(17) 0.0167(17) 0.0019(14) 0.0007(14) 0.0051(14) N2 0.0193(19) 0.0206(17) 0.0157(17) 0.0035(14) 0.0012(14) 0.0048(14) O1 0.0248(17) 0.0226(15) 0.0250(16) 0.0041(13) 0.0017(13) 0.0030(12) O2 0.0213(16) 0.0265(16) 0.0200(15) 0.0040(13) 0.0042(12) 0.0059(12) O3 0.0187(16) 0.0208(15) 0.0278(16) 0.0017(13) 0.0021(12) 0.0032(12) O4 0.0149(15) 0.0301(16) 0.0221(15) 0.0020(13) 0.0018(12) 0.0034(12) _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 O3 2.000(3) . ? Co1 O4 2.008(3) 2_667 ? Co1 O1 2.160(3) . ? Co1 N2 2.160(4) . ? Co1 O2 2.168(3) . ? Co1 N1 2.172(3) . ? Co1 C1 2.499(4) . ? C1 O1 1.267(5) . ? C1 O2 1.268(5) . ? C1 C2 1.487(6) . ? C2 C7 1.383(6) . ? C2 C3 1.390(6) . ? C3 C4 1.384(7) . ? C4 C5 1.375(7) . ? C5 C6 1.389(8) . ? C6 C7 1.386(7) . ? C8 O3 1.251(5) . ? C8 O4 1.266(5) . ? C8 C9 1.496(6) . ? C9 C10 1.388(6) . ? C9 C14 1.397(7) . ? C10 C11 1.385(7) . ? C11 C12 1.381(8) . ? C12 C13 1.383(8) . ? C13 C14 1.391(7) . ? C15 N1 1.340(5) . ? C15 C18 1.380(6) 1_655 ? C16 N1 1.342(5) . ? C16 C17 1.376(6) 1_655 ? C17 N2 1.341(5) . ? C17 C16 1.376(6) 1_455 ? C18 N2 1.339(6) . ? C18 C15 1.380(6) 1_455 ? O4 Co1 2.008(3) 2_667 ? O91 C91 1.265(8) . ? C91 O92 1.228(8) . ? C91 C92 1.507(14) . ? C92 C97 1.367(9) . ? C92 C93 1.398(9) . ? C93 C94 1.362(9) . ? C94 C95 1.361(9) . ? C95 C96 1.432(9) . ? C96 C97 1.421(9) . ? 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 O3 Co1 O4 113.37(13) . 2_667 ? O3 Co1 O1 91.78(12) . . ? O4 Co1 O1 154.70(13) 2_667 . ? O3 Co1 N2 93.60(13) . . ? O4 Co1 N2 91.26(12) 2_667 . ? O1 Co1 N2 89.80(12) . . ? O3 Co1 O2 151.41(12) . . ? O4 Co1 O2 93.92(12) 2_667 . ? O1 Co1 O2 60.80(11) . . ? N2 Co1 O2 94.17(12) . . ? O3 Co1 N1 86.83(12) . . ? O4 Co1 N1 88.01(12) 2_667 . ? O1 Co1 N1 90.79(12) . . ? N2 Co1 N1 179.26(13) . . ? O2 Co1 N1 85.73(12) . . ? O3 Co1 C1 121.40(13) . . ? O4 Co1 C1 124.35(14) 2_667 . ? O1 Co1 C1 30.45(13) . . ? N2 Co1 C1 94.42(13) . . ? O2 Co1 C1 30.48(12) . . ? N1 Co1 C1 85.87(13) . . ? O1 C1 O2 119.6(4) . . ? O1 C1 C2 119.9(4) . . ? O2 C1 C2 120.5(4) . . ? O1 C1 Co1 59.8(2) . . ? O2 C1 Co1 60.2(2) . . ? C2 C1 Co1 172.1(3) . . ? C7 C2 C3 119.0(4) . . ? C7 C2 C1 120.0(4) . . ? C3 C2 C1 120.8(4) . . ? C4 C3 C2 120.2(4) . . ? C5 C4 C3 120.3(5) . . ? C4 C5 C6 120.2(5) . . ? C7 C6 C5 119.2(5) . . ? C2 C7 C6 121.0(5) . . ? O3 C8 O4 124.4(4) . . ? O3 C8 C9 118.6(4) . . ? O4 C8 C9 117.0(4) . . ? C10 C9 C14 120.0(4) . . ? C10 C9 C8 120.0(4) . . ? C14 C9 C8 120.0(4) . . ? C11 C10 C9 120.1(5) . . ? C12 C11 C10 119.9(5) . . ? C11 C12 C13 120.4(4) . . ? C12 C13 C14 120.1(5) . . ? C13 C14 C9 119.3(5) . . ? N1 C15 C18 121.8(4) . 1_655 ? N1 C16 C17 121.4(4) . 1_655 ? N2 C17 C16 122.2(4) . 1_455 ? N2 C18 C15 121.7(4) . 1_455 ? C15 N1 C16 116.6(4) . . ? C15 N1 Co1 122.0(3) . . ? C16 N1 Co1 121.4(3) . . ? C18 N2 C17 116.3(4) . . ? C18 N2 Co1 120.8(3) . . ? C17 N2 Co1 122.8(3) . . ? C1 O1 Co1 89.8(3) . . ? C1 O2 Co1 89.3(2) . . ? C8 O3 Co1 152.4(3) . . ? C8 O4 Co1 126.0(3) . 2_667 ? O92 C91 O91 126.6(11) . . ? O92 C91 C92 117.9(8) . . ? O91 C91 C92 115.6(8) . . ? C97 C92 C93 117.4(9) . . ? C97 C92 C91 126.1(7) . . ? C93 C92 C91 116.5(7) . . ? C94 C93 C92 123.6(9) . . ? C95 C94 C93 119.0(9) . . ? C94 C95 C96 121.1(9) . . ? C97 C96 C95 117.0(9) . . ? C92 C97 C96 121.9(9) . . ? _diffrn_measured_fraction_theta_max 0.951 _diffrn_reflns_theta_full 67.54 _diffrn_measured_fraction_theta_full 0.951 _refine_diff_density_max 1.281 _refine_diff_density_min -0.475 _refine_diff_density_rms 0.092 _database_code_depnum_ccdc_archive 'CCDC 915207' ####################################################################### # # 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_compound-3_296K #TrackingRef '16069_web_deposit_cif_file_0_OscarCastillo_1355215083.CIFs.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; catena-Poly[[bis(benzoato-K2O,O')bis(mu-benzoato-KO:KO')bis(mu-pyrazine-KN,KN') dicobalt(II)]-benzoic acid (1/1)] ; _chemical_formula_moiety 'C18 H14 Co1 N2 O4, 1/2(C7 H6 O2)' _chemical_formula_structural 'C18 H14 Co1 N2 O4, 1/2(C7 H6 O2)' _chemical_formula_sum 'C21.50 H17 Co N2 O5' _chemical_formula_weight 442.30 _chemical_compound_source 'synthesis as described' 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' Co Co 0.3494 0.9721 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' _symmetry_Int_Tables_number 2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.1488(4) _cell_length_b 9.0736(8) _cell_length_c 15.7457(13) _cell_angle_alpha 95.506(7) _cell_angle_beta 93.239(6) _cell_angle_gamma 107.370(7) _cell_volume 966.37(13) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 7207 _cell_measurement_theta_min 2.37 _cell_measurement_theta_max 27.00 _cell_oxdiff_twin_number 2 loop_ _cell_oxdiff_twin_id _cell_oxdiff_twin_matrix_11 _cell_oxdiff_twin_matrix_12 _cell_oxdiff_twin_matrix_13 _cell_oxdiff_twin_matrix_21 _cell_oxdiff_twin_matrix_22 _cell_oxdiff_twin_matrix_23 _cell_oxdiff_twin_matrix_31 _cell_oxdiff_twin_matrix_32 _cell_oxdiff_twin_matrix_33 1 1.0000 0.0000 0.0000 0.0000 1.0000 0.0000 0.0000 0.0000 1.0000 2 1.0000 -0.0001 -0.0001 -0.7575 -0.9998 -0.0000 -0.2534 0.0004 -1.0003 loop_ _diffrn_oxdiff_twin_id _diffrn_oxdiff_twin_ratio _diffrn_oxdiff_twin_reflns_isolated _diffrn_oxdiff_twin_reflns_overlapped 1 0.3986 5400 2274 2 0.6014 5386 2274 _exptl_crystal_description prismatic _exptl_crystal_colour red _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.06 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.520 _exptl_crystal_density_method ? _exptl_crystal_F_000 454 _exptl_absorpt_coefficient_mu 0.925 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _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 Xcalibur _diffrn_measurement_method \w _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 7207 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0461 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.37 _diffrn_reflns_theta_max 27.00 _reflns_number_total 7207 _reflns_number_gt 5441 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlis CCD (Oxford Diffraction, 2003)' _computing_cell_refinement 'CrysAlis CCD (Oxford Diffraction, 2003)' _computing_data_reduction 'CrysAlis RED (Oxford Diffraction, 2003)' _computing_structure_solution 'Sir92 (Altamore et al., 1993)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 (Farrugia, 1997)' _computing_publication_material 'WinGX (Farrugia, 1999)' _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^)+(0.1075P)^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 7207 _refine_ls_number_parameters 263 _refine_ls_number_restraints 21 _refine_ls_R_factor_all 0.0735 _refine_ls_R_factor_gt 0.0559 _refine_ls_wR_factor_ref 0.1619 _refine_ls_wR_factor_gt 0.1545 _refine_ls_goodness_of_fit_ref 1.015 _refine_ls_restrained_S_all 1.035 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Co1 Co 0.61282(5) 0.67678(4) 0.92413(2) 0.02840(14) Uani 1 1 d . . . C1 C 0.6884(4) 0.8488(3) 0.80740(18) 0.0349(6) Uani 1 1 d . . . C2 C 0.7575(4) 0.9479(4) 0.73837(18) 0.0363(7) Uani 1 1 d . . . C3 C 0.8421(5) 1.1048(4) 0.7565(2) 0.0444(7) Uani 1 1 d . . . H3 H 0.8557 1.1525 0.8139 0.053 Uiso 1 1 calc R . . C4 C 0.9085(6) 1.1954(4) 0.6915(2) 0.0581(9) Uani 1 1 d . . . H4 H 0.9642 1.3049 0.7041 0.070 Uiso 1 1 calc R . . C5 C 0.8936(6) 1.1266(5) 0.6098(3) 0.0675(11) Uani 1 1 d . . . H5 H 0.9400 1.1886 0.5655 0.081 Uiso 1 1 calc R . . C6 C 0.8117(6) 0.9678(5) 0.5905(2) 0.0676(11) Uani 1 1 d . . . H6 H 0.8025 0.9206 0.5332 0.081 Uiso 1 1 calc R . . C7 C 0.7429(5) 0.8776(4) 0.6551(2) 0.0511(8) Uani 1 1 d . . . H7 H 0.6861 0.7682 0.6424 0.061 Uiso 1 1 calc R . . C8 C 0.4229(4) 0.3110(3) 0.89094(17) 0.0304(6) Uani 1 1 d . . . C9 C 0.3911(4) 0.2162(3) 0.80515(17) 0.0328(6) Uani 1 1 d . . . C10 C 0.2971(5) 0.0573(4) 0.7985(2) 0.0476(8) Uani 1 1 d . . . H10 H 0.2500 0.0095 0.8474 0.057 Uiso 1 1 calc R . . C11 C 0.2728(6) -0.0309(5) 0.7190(3) 0.0654(11) Uani 1 1 d . . . H11 H 0.2109 -0.1401 0.7139 0.078 Uiso 1 1 calc R . . C12 C 0.3363(6) 0.0370(6) 0.6491(2) 0.0745(13) Uani 1 1 d . . . H12 H 0.3171 -0.0246 0.5952 0.089 Uiso 1 1 calc R . . C13 C 0.4286(6) 0.1948(6) 0.6550(2) 0.0685(11) Uani 1 1 d . . . H13 H 0.4729 0.2413 0.6052 0.082 Uiso 1 1 calc R . . C14 C 0.4571(5) 0.2866(4) 0.73393(19) 0.0483(8) Uani 1 1 d . . . H14 H 0.5207 0.3955 0.7385 0.058 Uiso 1 1 calc R . . C15 C 0.9722(4) 0.5739(4) 0.87508(19) 0.0420(7) Uani 1 1 d . . . H15 H 0.8745 0.4974 0.8376 0.050 Uiso 1 1 calc R . . C16 C 1.0624(4) 0.7810(3) 0.97641(18) 0.0355(6) Uani 1 1 d . . . H16 H 1.0309 0.8572 1.0137 0.043 Uiso 1 1 calc R . . C17 C 0.2546(4) 0.7825(3) 0.97592(19) 0.0357(7) Uani 1 1 d . . . H17 H 0.3521 0.8594 1.0132 0.043 Uiso 1 1 calc R . . C18 C 0.1664(4) 0.5747(4) 0.87425(19) 0.0412(7) Uani 1 1 d . . . H18 H 0.1981 0.4988 0.8368 0.049 Uiso 1 1 calc R . . N1 N 0.9178(3) 0.6751(3) 0.92581(15) 0.0318(5) Uani 1 1 d . . . N2 N 0.3094(3) 0.6800(3) 0.92506(15) 0.0339(5) Uani 1 1 d . . . O1 O 0.60424(19) 0.7053(2) 0.78945(10) 0.0435(5) Uani 1 1 d D . . O2 O 0.7179(3) 0.9068(2) 0.88499(12) 0.0406(5) Uani 1 1 d . . . O3 O 0.5357(3) 0.4463(2) 0.89890(13) 0.0427(5) Uani 1 1 d . . . O4 O 0.3357(3) 0.2452(2) 0.95105(11) 0.0384(5) Uani 1 1 d . . . O91 O 0.2656(4) 0.6001(7) 0.6776(3) 0.111(2) Uiso 0.50 1 d PD A -1 H91 H 0.3762 0.6341 0.7072 0.167 Uiso 0.50 1 d PD B -1 C91 C 0.2953(13) 0.5540(5) 0.6041(5) 0.084(3) Uiso 0.50 1 d PD A -1 O92 O 0.4489(12) 0.5384(8) 0.5844(6) 0.145(3) Uiso 0.50 1 d PD A -1 C92 C 0.1215(11) 0.5161(8) 0.5376(4) 0.070(2) Uiso 0.50 1 d PD A -1 C93 C 0.1591(11) 0.4674(8) 0.4556(4) 0.065(2) Uiso 0.50 1 d PD A -1 H93 H 0.2872 0.4619 0.4465 0.077 Uiso 0.50 1 calc PR A -1 C94 C 0.0197(11) 0.4276(8) 0.3882(4) 0.074(2) Uiso 0.50 1 d PD A -1 H94 H 0.0505 0.3932 0.3333 0.089 Uiso 0.50 1 calc PR A -1 C95 C -0.1594(11) 0.4367(8) 0.3989(5) 0.076(2) Uiso 0.50 1 d PD A -1 H95 H -0.2568 0.4088 0.3516 0.091 Uiso 0.50 1 calc PR A -1 C96 C -0.2063(12) 0.4885(11) 0.4817(6) 0.115(4) Uiso 0.50 1 d PD A -1 H96 H -0.3337 0.4960 0.4904 0.138 Uiso 0.50 1 calc PR A -1 C97 C -0.0564(11) 0.5280(9) 0.5497(5) 0.090(3) Uiso 0.50 1 d PD A -1 H97 H -0.0830 0.5637 0.6050 0.108 Uiso 0.50 1 calc PR A -1 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 0.0221(2) 0.0332(2) 0.0306(2) 0.00218(14) 0.00379(15) 0.00975(16) C1 0.0271(14) 0.0410(17) 0.0410(16) 0.0077(12) 0.0056(12) 0.0156(13) C2 0.0316(14) 0.0426(17) 0.0380(16) 0.0106(13) 0.0041(12) 0.0146(13) C3 0.0465(18) 0.0459(19) 0.0434(17) 0.0068(14) 0.0033(14) 0.0180(15) C4 0.058(2) 0.051(2) 0.068(2) 0.0241(18) 0.0114(19) 0.0150(19) C5 0.077(3) 0.074(3) 0.062(2) 0.036(2) 0.022(2) 0.027(2) C6 0.084(3) 0.087(3) 0.0397(19) 0.0136(19) 0.0172(19) 0.033(3) C7 0.056(2) 0.056(2) 0.0434(18) 0.0081(15) 0.0084(15) 0.0189(17) C8 0.0234(13) 0.0369(16) 0.0345(15) 0.0005(12) -0.0002(11) 0.0164(12) C9 0.0261(14) 0.0426(16) 0.0317(14) -0.0019(12) 0.0022(11) 0.0157(12) C10 0.0470(19) 0.0426(18) 0.0521(19) -0.0036(14) -0.0037(14) 0.0165(15) C11 0.070(3) 0.051(2) 0.072(3) -0.0229(19) -0.015(2) 0.0261(19) C12 0.078(3) 0.104(4) 0.045(2) -0.032(2) -0.016(2) 0.049(3) C13 0.069(3) 0.111(4) 0.0326(18) 0.005(2) 0.0067(17) 0.040(3) C14 0.0433(18) 0.063(2) 0.0387(17) 0.0053(15) 0.0042(14) 0.0172(17) C15 0.0294(16) 0.0525(19) 0.0412(16) -0.0133(14) -0.0031(12) 0.0149(14) C16 0.0344(16) 0.0331(15) 0.0387(15) -0.0007(12) 0.0032(12) 0.0115(13) C17 0.0257(15) 0.0348(15) 0.0465(17) -0.0007(12) -0.0016(12) 0.0116(12) C18 0.0264(15) 0.058(2) 0.0410(16) -0.0120(14) -0.0021(12) 0.0220(14) N1 0.0211(11) 0.0395(13) 0.0368(13) 0.0032(10) 0.0035(9) 0.0128(10) N2 0.0258(12) 0.0415(14) 0.0351(13) 0.0042(10) 0.0022(9) 0.0117(10) O1 0.0458(12) 0.0385(12) 0.0421(12) 0.0045(9) 0.0017(10) 0.0070(11) O2 0.0434(12) 0.0437(12) 0.0356(11) 0.0041(9) 0.0056(9) 0.0143(10) O3 0.0395(12) 0.0327(11) 0.0508(13) -0.0040(9) 0.0057(10) 0.0062(10) O4 0.0307(10) 0.0494(12) 0.0312(10) 0.0008(9) 0.0058(8) 0.0070(10) _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 O3 1.990(2) . ? Co1 O4 1.9988(18) 2_667 ? Co1 O2 2.160(2) . ? Co1 O1 2.1605(17) . ? Co1 N2 2.179(2) . ? Co1 N1 2.183(2) . ? Co1 C1 2.503(3) . ? Co1 Co1 4.1736(8) 2_667 ? Co1 Co1 7.1488(4) 1_655 ? C1 O1 1.257(3) . ? C1 O2 1.263(3) . ? C1 C2 1.489(4) . ? C2 C3 1.365(4) . ? C2 C7 1.386(4) . ? C3 C4 1.390(5) . ? C4 C5 1.359(5) . ? C5 C6 1.380(6) . ? C6 C7 1.388(5) . ? C8 O3 1.241(3) . ? C8 O4 1.262(3) . ? C8 C9 1.498(4) . ? C9 C14 1.380(4) . ? C9 C10 1.388(4) . ? C10 C11 1.393(5) . ? C11 C12 1.347(6) . ? C12 C13 1.377(6) . ? C13 C14 1.397(5) . ? C15 N1 1.320(4) . ? C15 C18 1.387(4) 1_655 ? C16 N1 1.339(3) . ? C16 C17 1.371(4) 1_655 ? C17 N2 1.330(4) . ? C17 C16 1.371(4) 1_455 ? C18 N2 1.333(4) . ? C18 C15 1.387(4) 1_455 ? O4 Co1 1.9988(18) 2_667 ? O91 C91 1.244(7) . ? C91 O92 1.202(8) . ? C91 C92 1.512(11) . ? C92 C97 1.330(8) . ? C92 C93 1.392(8) . ? C93 C94 1.357(7) . ? C94 C95 1.327(8) . ? C95 C96 1.435(9) . ? C96 C97 1.411(8) . ? 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 O3 Co1 O4 114.13(9) . 2_667 ? O3 Co1 O2 151.24(9) . . ? O4 Co1 O2 93.56(8) 2_667 . ? O3 Co1 O1 91.92(8) . . ? O4 Co1 O1 153.86(8) 2_667 . ? O2 Co1 O1 60.33(7) . . ? O3 Co1 N2 93.50(9) . . ? O4 Co1 N2 90.78(8) 2_667 . ? O2 Co1 N2 93.75(9) . . ? O1 Co1 N2 89.71(7) . . ? O3 Co1 N1 86.95(9) . . ? O4 Co1 N1 88.12(8) 2_667 . ? O2 Co1 N1 86.32(8) . . ? O1 Co1 N1 91.28(7) . . ? N2 Co1 N1 178.90(8) . . ? O3 Co1 C1 121.35(9) . . ? O4 Co1 C1 123.84(10) 2_667 . ? O2 Co1 C1 30.31(8) . . ? O1 Co1 C1 30.13(8) . . ? N2 Co1 C1 93.88(9) . . ? N1 Co1 C1 86.73(9) . . ? O3 Co1 Co1 48.46(6) . 2_667 ? O4 Co1 Co1 68.20(6) 2_667 2_667 ? O2 Co1 Co1 160.21(6) . 2_667 ? O1 Co1 Co1 137.33(5) . 2_667 ? N2 Co1 Co1 79.43(6) . 2_667 ? N1 Co1 Co1 100.15(6) . 2_667 ? C1 Co1 Co1 166.66(7) . 2_667 ? O3 Co1 Co1 87.26(6) . 1_655 ? O4 Co1 Co1 88.69(6) 2_667 1_655 ? O2 Co1 Co1 85.68(6) . 1_655 ? O1 Co1 Co1 90.50(4) . 1_655 ? N2 Co1 Co1 179.20(7) . 1_655 ? N1 Co1 Co1 0.83(6) . 1_655 ? C1 Co1 Co1 85.92(6) . 1_655 ? Co1 Co1 Co1 100.916(11) 2_667 1_655 ? O1 C1 O2 119.0(3) . . ? O1 C1 C2 120.4(3) . . ? O2 C1 C2 120.6(3) . . ? O1 C1 Co1 59.67(13) . . ? O2 C1 Co1 59.64(14) . . ? C2 C1 Co1 172.9(2) . . ? C3 C2 C7 119.9(3) . . ? C3 C2 C1 121.1(3) . . ? C7 C2 C1 118.9(3) . . ? C2 C3 C4 120.4(3) . . ? C5 C4 C3 119.7(3) . . ? C4 C5 C6 120.7(3) . . ? C5 C6 C7 119.6(4) . . ? C2 C7 C6 119.6(3) . . ? O3 C8 O4 124.5(3) . . ? O3 C8 C9 118.5(3) . . ? O4 C8 C9 117.0(2) . . ? C14 C9 C10 120.7(3) . . ? C14 C9 C8 120.0(3) . . ? C10 C9 C8 119.3(3) . . ? C9 C10 C11 119.0(4) . . ? C12 C11 C10 120.6(4) . . ? C11 C12 C13 120.8(3) . . ? C12 C13 C14 120.1(4) . . ? C9 C14 C13 118.8(4) . . ? N1 C15 C18 122.6(3) . 1_655 ? N1 C16 C17 121.8(3) . 1_655 ? N2 C17 C16 122.3(3) . 1_455 ? N2 C18 C15 121.1(3) . 1_455 ? C15 N1 C16 115.9(2) . . ? C15 N1 Co1 122.31(19) . . ? C16 N1 Co1 121.77(19) . . ? C17 N2 C18 116.2(2) . . ? C17 N2 Co1 123.27(19) . . ? C18 N2 Co1 120.49(19) . . ? C1 O1 Co1 90.20(15) . . ? C1 O2 Co1 90.06(17) . . ? C8 O3 Co1 156.3(2) . . ? C8 O4 Co1 126.57(18) . 2_667 ? O92 C91 O91 124.4(9) . . ? O92 C91 C92 120.2(8) . . ? O91 C91 C92 115.4(6) . . ? C97 C92 C93 118.6(7) . . ? C97 C92 C91 127.0(6) . . ? C93 C92 C91 114.4(6) . . ? C94 C93 C92 122.5(7) . . ? C95 C94 C93 120.0(7) . . ? C94 C95 C96 120.1(7) . . ? C97 C96 C95 117.6(8) . . ? C92 C97 C96 121.2(7) . . ? _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 27.00 _diffrn_measured_fraction_theta_full 0.987 _refine_diff_density_max 1.223 _refine_diff_density_min -0.463 _refine_diff_density_rms 0.082 _database_code_depnum_ccdc_archive 'CCDC 915208' ####################################################################### # # 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_compound-4 #TrackingRef '16069_web_deposit_cif_file_0_OscarCastillo_1355215083.CIFs.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; catena-Poly[[bis(benzoato-K2O,O')bis(mu-benzoato-KO:KO')bis(mu-pyrazine-KN,KN') diiron(II)]-benzoic acid (1/1)] ; _chemical_formula_moiety 'C18 H14 Fe N2 O4, 1/2(C7 H6 O2)' _chemical_formula_structural 'C18 H14 Fe N2 O4, 1/2(C7 H6 O2)' _chemical_formula_sum 'C21.50 H17 Fe N2 O5' _chemical_formula_weight 439.22 _chemical_compound_source 'synthesis as described' 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' Fe Fe 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' _symmetry_Int_Tables_number 2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.268(7) _cell_length_b 9.209(6) _cell_length_c 15.814(9) _cell_angle_alpha 95.72(4) _cell_angle_beta 92.91(5) _cell_angle_gamma 109.02(5) _cell_volume 991.8(13) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 9733 _cell_measurement_theta_min 2.98 _cell_measurement_theta_max 28.43 _exptl_crystal_description prismatic _exptl_crystal_colour 'dark blue' _exptl_crystal_size_max 0.16 _exptl_crystal_size_mid 0.04 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.471 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 452 _exptl_absorpt_coefficient_mu 0.796 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _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 Xcalibur _diffrn_measurement_method \w _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 9733 _diffrn_reflns_av_R_equivalents 0.0723 _diffrn_reflns_av_sigmaI/netI 0.0844 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.98 _diffrn_reflns_theta_max 28.43 _reflns_number_total 4925 _reflns_number_gt 1509 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlis CCD (Oxford Diffraction, 2003)' _computing_cell_refinement 'CrysAlis CCD (Oxford Diffraction, 2003)' _computing_data_reduction 'CrysAlis RED (Oxford Diffraction, 2003)' _computing_structure_solution 'Sir92 (Altamore et al., 1993)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 (Farrugia, 1997)' _computing_publication_material 'WinGX (Farrugia, 1999)' _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. The benzoic acid molecule is dissordered over two symmetry center related positions, and their non-hydrogen atoms have been isotrophically refined. ; _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^)+(0.0083P)^2^+0.9660P] 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 4925 _refine_ls_number_parameters 262 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.2462 _refine_ls_R_factor_gt 0.0598 _refine_ls_wR_factor_ref 0.1223 _refine_ls_wR_factor_gt 0.0872 _refine_ls_goodness_of_fit_ref 0.951 _refine_ls_restrained_S_all 0.951 _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 0.59992(14) 0.67617(14) 0.92664(7) 0.0345(3) Uani 1 1 d . . . C1 C 0.6845(9) 0.8479(10) 0.8096(5) 0.0428(19) Uani 1 1 d . . . C2 C 0.7578(8) 0.9441(10) 0.7400(5) 0.0454(19) Uani 1 1 d . . . C3 C 0.8416(9) 1.1037(10) 0.7535(5) 0.052(2) Uani 1 1 d . . . H3 H 0.8527 1.1552 0.8096 0.063 Uiso 1 1 calc R . . C4 C 0.9087(11) 1.1898(11) 0.6891(7) 0.075(3) Uani 1 1 d . . . H4 H 0.9660 1.2991 0.7008 0.090 Uiso 1 1 calc R . . C5 C 0.8933(12) 1.1181(15) 0.6070(6) 0.080(3) Uani 1 1 d . . . H5 H 0.9378 1.1772 0.5616 0.096 Uiso 1 1 calc R . . C6 C 0.8128(12) 0.9600(13) 0.5918(6) 0.081(3) Uani 1 1 d . . . H6 H 0.8027 0.9089 0.5357 0.098 Uiso 1 1 calc R . . C7 C 0.7473(9) 0.8760(10) 0.6569(5) 0.060(2) Uani 1 1 d . . . H7 H 0.6922 0.7666 0.6449 0.072 Uiso 1 1 calc R . . C8 C 0.4138(8) 0.3007(9) 0.8890(4) 0.0357(17) Uani 1 1 d . . . C9 C 0.3886(8) 0.2110(9) 0.8033(4) 0.0424(18) Uani 1 1 d . . . C10 C 0.3046(10) 0.0549(10) 0.7927(5) 0.054(2) Uani 1 1 d . . . H10 H 0.2579 0.0022 0.8401 0.065 Uiso 1 1 calc R . . C11 C 0.2868(12) -0.0274(12) 0.7135(8) 0.087(3) Uani 1 1 d . . . H11 H 0.2253 -0.1365 0.7064 0.105 Uiso 1 1 calc R . . C12 C 0.3553(13) 0.0446(16) 0.6457(7) 0.093(4) Uani 1 1 d . . . H12 H 0.3480 -0.0142 0.5920 0.112 Uiso 1 1 calc R . . C13 C 0.4342(12) 0.2003(15) 0.6543(5) 0.087(3) Uani 1 1 d . . . H13 H 0.4754 0.2517 0.6058 0.104 Uiso 1 1 calc R . . C14 C 0.4551(9) 0.2849(9) 0.7333(5) 0.058(2) Uani 1 1 d . . . H14 H 0.5152 0.3942 0.7397 0.069 Uiso 1 1 calc R . . C15 C 0.9596(10) 0.5695(8) 0.8797(5) 0.050(2) Uani 1 1 d . . . H15 H 0.8604 0.4912 0.8437 0.060 Uiso 1 1 calc R . . C16 C 1.0555(9) 0.7819(8) 0.9779(4) 0.0432(19) Uani 1 1 d . . . H16 H 1.0281 0.8594 1.0142 0.052 Uiso 1 1 calc R . . C17 C 0.2464(9) 0.7840(8) 0.9765(4) 0.0422(19) Uani 1 1 d . . . H17 H 0.3459 0.8633 1.0119 0.051 Uiso 1 1 calc R . . C18 C 0.1471(9) 0.5714(8) 0.8787(5) 0.050(2) Uani 1 1 d . . . H18 H 0.1749 0.4942 0.8423 0.060 Uiso 1 1 calc R . . N1 N 0.9096(7) 0.6750(7) 0.9300(4) 0.0453(15) Uani 1 1 d . . . N2 N 0.2953(7) 0.6802(7) 0.9281(4) 0.0434(15) Uani 1 1 d . . . O1 O 0.6042(6) 0.7044(6) 0.7914(3) 0.0494(13) Uani 1 1 d . . . O2 O 0.7151(5) 0.9116(5) 0.8857(3) 0.0491(13) Uani 1 1 d . . . O3 O 0.5039(6) 0.4432(6) 0.8979(3) 0.0561(14) Uani 1 1 d . . . O4 O 0.3440(5) 0.2281(6) 0.9489(3) 0.0504(13) Uani 1 1 d . . . O91 O 0.2663(17) 0.5982(14) 0.6790(9) 0.135(5) Uiso 0.50 1 d PD A -1 H91 H 0.3742 0.6095 0.7128 0.203 Uiso 0.50 1 d P B -1 C91 C 0.295(2) 0.5522(10) 0.6039(10) 0.100(7) Uiso 0.50 1 d PD A -1 O92 O 0.444(2) 0.5361(13) 0.5830(11) 0.170(7) Uiso 0.50 1 d PD A -1 C92 C 0.122(3) 0.5162(12) 0.5382(7) 0.093(6) Uiso 0.50 1 d PD A -1 C93 C 0.158(2) 0.4680(12) 0.4570(7) 0.070(5) Uiso 0.50 1 d PD A -1 H93 H 0.2836 0.4617 0.4471 0.084 Uiso 0.50 1 calc PR A -1 C94 C 0.016(2) 0.4293(16) 0.3906(8) 0.124(8) Uiso 0.50 1 d PD A -1 H94 H 0.0391 0.3929 0.3352 0.149 Uiso 0.50 1 calc PR A -1 C95 C -0.158(2) 0.4443(16) 0.4057(8) 0.084(6) Uiso 0.50 1 d PD A -1 H95 H -0.2580 0.4210 0.3602 0.101 Uiso 0.50 1 calc PR A -1 C96 C -0.1932(19) 0.4937(16) 0.4880(10) 0.103(7) Uiso 0.50 1 d PD A -1 H96 H -0.3156 0.5034 0.5002 0.123 Uiso 0.50 1 calc PR A -1 C97 C -0.0384(18) 0.5284(14) 0.5518(9) 0.094(7) Uiso 0.50 1 d PD A -1 H97 H -0.0581 0.5630 0.6082 0.113 Uiso 0.50 1 calc PR A -1 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 0.0302(5) 0.0367(7) 0.0353(6) 0.0023(5) 0.0026(4) 0.0101(4) C1 0.040(4) 0.051(6) 0.043(5) 0.007(4) 0.009(3) 0.022(4) C2 0.034(4) 0.049(6) 0.049(5) -0.004(4) 0.004(3) 0.011(3) C3 0.058(5) 0.045(6) 0.052(5) 0.013(5) 0.004(4) 0.013(4) C4 0.075(6) 0.047(7) 0.098(8) 0.028(6) 0.004(5) 0.008(4) C5 0.075(6) 0.112(10) 0.069(7) 0.046(7) 0.029(5) 0.040(6) C6 0.107(7) 0.076(8) 0.060(6) 0.002(6) 0.021(5) 0.029(6) C7 0.068(5) 0.059(6) 0.052(5) 0.005(5) 0.016(4) 0.018(4) C8 0.023(3) 0.050(5) 0.035(4) -0.009(4) -0.002(3) 0.018(3) C9 0.031(4) 0.053(6) 0.044(5) -0.003(4) 0.000(3) 0.019(3) C10 0.074(5) 0.039(6) 0.044(5) -0.012(4) -0.002(4) 0.018(4) C11 0.087(7) 0.069(8) 0.098(9) -0.027(7) -0.013(6) 0.028(5) C12 0.094(7) 0.115(11) 0.063(7) -0.043(8) -0.016(5) 0.044(7) C13 0.106(7) 0.125(11) 0.029(5) -0.006(6) 0.008(4) 0.042(7) C14 0.049(4) 0.062(6) 0.055(5) -0.005(5) -0.001(4) 0.013(4) C15 0.044(4) 0.038(5) 0.057(5) -0.022(4) 0.003(4) 0.006(4) C16 0.052(5) 0.034(5) 0.039(4) -0.008(4) -0.001(3) 0.012(4) C17 0.028(4) 0.044(5) 0.051(5) -0.003(4) -0.002(3) 0.010(3) C18 0.033(4) 0.046(6) 0.070(5) -0.028(5) 0.004(4) 0.022(4) N1 0.035(3) 0.065(5) 0.040(3) 0.005(3) 0.003(3) 0.023(3) N2 0.033(3) 0.055(4) 0.045(4) 0.001(3) 0.006(3) 0.019(3) O1 0.066(3) 0.031(3) 0.047(3) 0.008(3) 0.005(2) 0.011(2) O2 0.055(3) 0.052(4) 0.041(3) 0.008(3) 0.006(2) 0.017(2) O3 0.057(3) 0.034(4) 0.068(4) -0.010(3) -0.003(2) 0.008(2) O4 0.044(3) 0.063(4) 0.035(3) -0.010(3) 0.004(2) 0.010(2) _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 O3 2.023(5) . ? Fe1 O4 2.038(4) 2_667 ? Fe1 O1 2.181(5) . ? Fe1 N2 2.228(5) . ? Fe1 O2 2.230(5) . ? Fe1 N1 2.253(5) . ? C1 O1 1.255(8) . ? C1 O2 1.260(7) . ? C1 C2 1.491(9) . ? C2 C3 1.385(10) . ? C2 C7 1.385(9) . ? C3 C4 1.366(10) . ? C3 H3 0.9500 . ? C4 C5 1.379(12) . ? C4 H4 0.9500 . ? C5 C6 1.371(12) . ? C5 H5 0.9500 . ? C6 C7 1.361(10) . ? C6 H6 0.9500 . ? C7 H7 0.9500 . ? C8 O4 1.247(7) . ? C8 O3 1.251(8) . ? C8 C9 1.486(9) . ? C9 C10 1.355(9) . ? C9 C14 1.382(9) . ? C10 C11 1.375(11) . ? C10 H10 0.9500 . ? C11 C12 1.348(12) . ? C11 H11 0.9500 . ? C12 C13 1.349(13) . ? C12 H12 0.9500 . ? C13 C14 1.379(11) . ? C13 H13 0.9500 . ? C14 H14 0.9500 . ? C15 N1 1.347(8) . ? C15 C18 1.358(8) 1_655 ? C15 H15 0.9500 . ? C16 N1 1.325(8) . ? C16 C17 1.382(7) 1_655 ? C16 H16 0.9500 . ? C17 N2 1.315(8) . ? C17 C16 1.382(7) 1_455 ? C17 H17 0.9500 . ? C18 N2 1.353(8) . ? C18 C15 1.358(8) 1_455 ? C18 H18 0.9500 . ? O4 Fe1 2.038(4) 2_667 ? O91 C91 1.271(9) . ? O91 H91 0.8969 . ? C91 O92 1.202(9) . ? C91 C92 1.51(2) . ? C92 C97 1.24(2) . ? C92 C93 1.382(10) . ? C93 C94 1.371(9) . ? C93 H93 0.9500 . ? C94 C95 1.347(9) . ? C94 H94 0.9500 . ? C95 C96 1.399(10) . ? C95 H95 0.9500 . ? C96 C97 1.404(10) . ? C96 H96 0.9500 . ? C97 H97 0.9500 . ? 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 O3 Fe1 O4 119.7(2) . 2_667 ? O3 Fe1 O1 90.6(2) . . ? O4 Fe1 O1 149.6(2) 2_667 . ? O3 Fe1 N2 91.6(2) . . ? O4 Fe1 N2 89.76(19) 2_667 . ? O1 Fe1 N2 91.83(18) . . ? O3 Fe1 O2 149.96(18) . . ? O4 Fe1 O2 89.9(2) 2_667 . ? O1 Fe1 O2 59.71(18) . . ? N2 Fe1 O2 93.56(19) . . ? O3 Fe1 N1 89.2(2) . . ? O4 Fe1 N1 88.27(19) 2_667 . ? O1 Fe1 N1 89.97(18) . . ? N2 Fe1 N1 178.0(2) . . ? O2 Fe1 N1 86.61(19) . . ? O1 C1 O2 121.7(7) . . ? O1 C1 C2 119.1(7) . . ? O2 C1 C2 119.1(7) . . ? C3 C2 C7 116.0(8) . . ? C3 C2 C1 123.2(7) . . ? C7 C2 C1 120.9(8) . . ? C4 C3 C2 122.4(8) . . ? C4 C3 H3 118.8 . . ? C2 C3 H3 118.8 . . ? C3 C4 C5 120.0(9) . . ? C3 C4 H4 120.0 . . ? C5 C4 H4 120.0 . . ? C6 C5 C4 118.9(9) . . ? C6 C5 H5 120.5 . . ? C4 C5 H5 120.5 . . ? C7 C6 C5 120.2(9) . . ? C7 C6 H6 119.9 . . ? C5 C6 H6 119.9 . . ? C6 C7 C2 122.5(8) . . ? C6 C7 H7 118.7 . . ? C2 C7 H7 118.7 . . ? O4 C8 O3 123.4(6) . . ? O4 C8 C9 117.4(7) . . ? O3 C8 C9 119.1(7) . . ? C10 C9 C14 118.9(7) . . ? C10 C9 C8 120.6(7) . . ? C14 C9 C8 120.5(7) . . ? C9 C10 C11 120.1(8) . . ? C9 C10 H10 120.0 . . ? C11 C10 H10 120.0 . . ? C12 C11 C10 121.0(10) . . ? C12 C11 H11 119.5 . . ? C10 C11 H11 119.5 . . ? C11 C12 C13 119.9(10) . . ? C11 C12 H12 120.1 . . ? C13 C12 H12 120.1 . . ? C12 C13 C14 120.0(10) . . ? C12 C13 H13 120.0 . . ? C14 C13 H13 120.0 . . ? C13 C14 C9 120.1(8) . . ? C13 C14 H14 119.9 . . ? C9 C14 H14 119.9 . . ? N1 C15 C18 122.2(6) . 1_655 ? N1 C15 H15 118.9 . . ? C18 C15 H15 118.9 1_655 . ? N1 C16 C17 122.0(6) . 1_655 ? N1 C16 H16 119.0 . . ? C17 C16 H16 119.0 1_655 . ? N2 C17 C16 122.4(6) . 1_455 ? N2 C17 H17 118.8 . . ? C16 C17 H17 118.8 1_455 . ? N2 C18 C15 121.8(6) . 1_455 ? N2 C18 H18 119.1 . . ? C15 C18 H18 119.1 1_455 . ? C16 N1 C15 115.7(6) . . ? C16 N1 Fe1 122.5(5) . . ? C15 N1 Fe1 121.7(5) . . ? C17 N2 C18 115.8(5) . . ? C17 N2 Fe1 123.5(4) . . ? C18 N2 Fe1 120.7(5) . . ? C1 O1 Fe1 90.4(4) . . ? C1 O2 Fe1 88.1(4) . . ? C8 O3 Fe1 167.4(4) . . ? C8 O4 Fe1 122.9(4) . 2_667 ? C91 O91 H91 107.3 . . ? O92 C91 O91 125.1(16) . . ? O92 C91 C92 119.8(14) . . ? O91 C91 C92 115.1(13) . . ? C97 C92 C93 120.5(14) . . ? C97 C92 C91 125.8(11) . . ? C93 C92 C91 113.7(12) . . ? C94 C93 C92 120.7(13) . . ? C94 C93 H93 119.6 . . ? C92 C93 H93 119.6 . . ? C95 C94 C93 118.5(13) . . ? C95 C94 H94 120.7 . . ? C93 C94 H94 120.8 . . ? C94 C95 C96 120.3(13) . . ? C94 C95 H95 119.9 . . ? C96 C95 H95 119.9 . . ? C95 C96 C97 116.8(13) . . ? C95 C96 H96 121.6 . . ? C97 C96 H96 121.6 . . ? C92 C97 C96 123.2(15) . . ? C92 C97 H97 118.4 . . ? C96 C97 H97 118.4 . . ? _diffrn_measured_fraction_theta_max 0.986 _diffrn_reflns_theta_full 28.43 _diffrn_measured_fraction_theta_full 0.986 _refine_diff_density_max 0.412 _refine_diff_density_min -0.320 _refine_diff_density_rms 0.065 _database_code_depnum_ccdc_archive 'CCDC 915209'