Supplementary Material (ESI) for Dalton Transactions This journal is (c) The Royal Society of Chemistry 2007 data_global _journal_coden_Cambridge 222 loop_ _publ_author_name 'P. Bernhardt' 'Piao Chin' 'Des R. Richardson' 'Philip C. Sharpe' _publ_contact_author_name 'Paul Bernhardt' _publ_contact_author_address ; Department of Chemistry University of Queensland Brisbane 4072 AUSTRALIA ; _publ_contact_author_email P.BERNHARDT@UQ.EDU.AU _publ_requested_journal 'Dalton Transactions' _publ_section_title ; Hydrazone chelators for the treatment of iron overload disorders: iron coordination chemistry and biological activity ; _publ_requested_category FO data_ac40343 _database_code_depnum_ccdc_archive 'CCDC 640839' _audit_creation_date 2007-03-16T15:01:38-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.3 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C12 H14 N4 O3' _chemical_formula_sum 'C12 H14 N4 O3' _chemical_formula_weight 262.27 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _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 6.4200(10) _cell_length_b 8.0010(10) _cell_length_c 12.943(2) _cell_angle_alpha 87.76(2) _cell_angle_beta 76.47(2) _cell_angle_gamma 80.730(10) _cell_volume 637.94(16) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 10.363 _cell_measurement_theta_max 14.116 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.5 _exptl_crystal_size_mid 0.4 _exptl_crystal_size_min 0.3 _exptl_crystal_density_diffrn 1.365 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 276 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.101 _exptl_absorpt_correction_type none #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_source 'Enraf Nonius FR590' _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_detector 'scintillation LiI' _diffrn_detector_dtime 1.195 _diffrn_orient_matrix_type ; x-axis points to radiation source the matrix is specified in reciprocal space ; _diffrn_orient_matrix_ub_11 -0.11544 _diffrn_orient_matrix_ub_12 0.089704 _diffrn_orient_matrix_ub_13 -0.016471 _diffrn_orient_matrix_ub_21 -0.083215 _diffrn_orient_matrix_ub_22 -0.089349 _diffrn_orient_matrix_ub_23 -0.013119 _diffrn_orient_matrix_ub_31 -0.077783 _diffrn_orient_matrix_ub_32 0.003827 _diffrn_orient_matrix_ub_33 0.076633 _diffrn_measurement_device '\k-geometry diffractometer' _diffrn_measurement_device_type 'Enraf Nonius CAD4' _diffrn_measurement_method 'non-profiled omega/2theta scans' _diffrn_standards_number 3 _diffrn_standards_interval_time 120 _diffrn_standards_decay_% 0 loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l -2 -4 -2 -3 3 -3 -2 -1 5 _diffrn_reflns_av_R_equivalents 0.0117 _diffrn_reflns_av_unetI/netI 0.017 _diffrn_reflns_number 2466 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.62 _diffrn_reflns_theta_max 24.96 _diffrn_reflns_theta_full 24.96 _diffrn_measured_fraction_theta_full 1 _diffrn_measured_fraction_theta_max 1 _reflns_number_total 2247 _reflns_number_gt 1720 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'CAD4 Express (Enraf Nonius, 1994)' _computing_cell_refinement 'CAD4 Express (Enraf Nonius, 1994)' _computing_data_reduction 'XCAD4 (Harms & Wocadlo, 1995)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.0521P)^2^+0.1097P] 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_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_coef 0.056(6) _refine_ls_number_reflns 2247 _refine_ls_number_parameters 173 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.051 _refine_ls_R_factor_gt 0.0341 _refine_ls_wR_factor_ref 0.1017 _refine_ls_wR_factor_gt 0.0914 _refine_ls_goodness_of_fit_ref 1.027 _refine_ls_restrained_S_all 1.027 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.238 _refine_diff_density_min -0.161 _refine_diff_density_rms 0.032 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 C1 C 1.0531(3) 0.1096(2) -0.16202(13) 0.0546(4) Uani 1 1 d . . . H1 H 0.9925 0.0758 -0.2149 0.066 Uiso 1 1 calc R . . C2 C 1.2712(3) 0.0605(2) -0.17028(13) 0.0529(4) Uani 1 1 d . . . H2 H 1.3553 -0.0061 -0.2268 0.063 Uiso 1 1 calc R . . C3 C 1.3632(2) 0.1117(2) -0.09340(12) 0.0513(4) Uani 1 1 d . . . H3 H 1.5114 0.0827 -0.0981 0.062 Uiso 1 1 calc R . . C4 C 1.2320(2) 0.20657(19) -0.00920(12) 0.0466(4) Uani 1 1 d . . . H4 H 1.29 0.2418 0.0442 0.056 Uiso 1 1 calc R . . C5 C 1.0127(2) 0.24855(17) -0.00544(11) 0.0391(3) Uani 1 1 d . . . C6 C 0.8587(2) 0.34832(18) 0.08029(11) 0.0417(4) Uani 1 1 d . . . H6 H 0.7156 0.3806 0.0753 0.05 Uiso 1 1 calc R . . C7 C 0.8122(2) 0.54020(19) 0.32225(11) 0.0415(3) Uani 1 1 d . . . C8 C 0.6363(2) 0.64482(18) 0.40077(11) 0.0399(3) Uani 1 1 d . . . C9 C 0.4307(2) 0.7071(2) 0.38646(13) 0.0527(4) Uani 1 1 d . . . H9 H 0.3922 0.6857 0.3239 0.063 Uiso 1 1 calc R . . C10 C 0.2844(3) 0.8009(2) 0.46613(14) 0.0594(5) Uani 1 1 d . . . H10 H 0.1453 0.8432 0.4583 0.071 Uiso 1 1 calc R . . C11 C 0.3457(3) 0.8312(2) 0.55687(13) 0.0580(4) Uani 1 1 d . . . H11 H 0.2449 0.895 0.61 0.07 Uiso 1 1 calc R . . C12 C 0.6823(3) 0.6825(2) 0.49577(12) 0.0493(4) Uani 1 1 d . . . H12 H 0.8198 0.6412 0.5062 0.059 Uiso 1 1 calc R . . N1 N 0.92302(19) 0.20364(16) -0.08197(10) 0.0473(3) Uani 1 1 d . . . N2 N 0.91689(18) 0.39163(15) 0.16139(9) 0.0413(3) Uani 1 1 d . . . N3 N 0.75802(18) 0.48765(15) 0.23576(9) 0.0412(3) Uani 1 1 d . . . H3A H 0.6278 0.5133 0.2272 0.049 Uiso 1 1 calc R . . N4 N 0.5418(2) 0.77444(19) 0.57339(11) 0.0593(4) Uani 1 1 d . . . O1 O 0.99610(16) 0.50520(16) 0.33684(8) 0.0606(4) Uani 1 1 d . . . O2 O 0.36489(16) 0.53538(15) 0.16413(9) 0.0599(3) Uani 1 1 d . . . H21 H 0.3045 0.6157 0.1327 0.09 Uiso 1 1 d R . . H22 H 0.2613 0.4978 0.2031 0.09 Uiso 1 1 d R . . O3 O 0.7939(2) 0.87225(17) 0.71832(12) 0.0862(5) Uani 1 1 d . . . H31 H 0.8663 0.7776 0.7314 0.129 Uiso 1 1 d R . . H32 H 0.7027 0.8397 0.6842 0.129 Uiso 1 1 d 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 C1 0.0569(10) 0.0620(10) 0.0457(9) -0.0157(8) -0.0119(7) -0.0077(8) C2 0.0553(10) 0.0526(9) 0.0431(9) -0.0085(7) -0.0002(7) -0.0002(7) C3 0.0411(8) 0.0588(10) 0.0477(9) -0.0001(7) -0.0052(7) 0.0036(7) C4 0.0418(8) 0.0571(9) 0.0408(8) -0.0039(7) -0.0120(7) -0.0027(7) C5 0.0400(8) 0.0403(8) 0.0360(7) -0.0014(6) -0.0084(6) -0.0037(6) C6 0.0348(7) 0.0484(8) 0.0413(8) -0.0051(6) -0.0101(6) -0.0018(6) C7 0.0357(7) 0.0526(9) 0.0357(8) -0.0012(6) -0.0093(6) -0.0041(6) C8 0.0392(7) 0.0453(8) 0.0351(7) -0.0013(6) -0.0070(6) -0.0080(6) C9 0.0461(9) 0.0681(10) 0.0430(9) -0.0123(7) -0.0131(7) 0.0009(7) C10 0.0429(9) 0.0720(12) 0.0589(10) -0.0165(9) -0.0097(7) 0.0052(8) C11 0.0570(10) 0.0622(11) 0.0479(9) -0.0191(8) -0.0010(8) -0.0016(8) C12 0.0455(8) 0.0614(10) 0.0418(8) -0.0080(7) -0.0113(7) -0.0071(7) N1 0.0440(7) 0.0542(8) 0.0444(7) -0.0105(6) -0.0120(6) -0.0043(6) N2 0.0356(6) 0.0482(7) 0.0376(6) -0.0050(5) -0.0065(5) -0.0006(5) N3 0.0307(6) 0.0526(7) 0.0381(6) -0.0082(5) -0.0078(5) 0.0016(5) N4 0.0611(9) 0.0712(10) 0.0453(8) -0.0167(7) -0.0117(7) -0.0066(7) O1 0.0395(6) 0.0948(9) 0.0459(6) -0.0153(6) -0.0147(5) 0.0050(6) O2 0.0361(6) 0.0806(8) 0.0634(7) -0.0035(6) -0.0149(5) -0.0043(5) O3 0.0897(10) 0.0766(9) 0.1023(11) -0.0284(8) -0.0556(9) 0.0137(7) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 C1 N1 1.3381(19) . ? C1 C2 1.372(2) . ? C2 C3 1.375(2) . ? C3 C4 1.379(2) . ? C4 C5 1.3838(19) . ? C5 N1 1.3427(18) . ? C5 C6 1.465(2) . ? C6 N2 1.2708(18) . ? C7 O1 1.2254(17) . ? C7 N3 1.3480(18) . ? C7 C8 1.495(2) . ? C8 C12 1.385(2) . ? C8 C9 1.385(2) . ? C9 C10 1.374(2) . ? C10 C11 1.364(2) . ? C11 N4 1.331(2) . ? C12 N4 1.336(2) . ? N2 N3 1.3795(16) . ? 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 C1 C2 123.46(14) . . ? C1 C2 C3 118.80(14) . . ? C2 C3 C4 118.87(14) . . ? C3 C4 C5 118.93(14) . . ? N1 C5 C4 122.49(13) . . ? N1 C5 C6 114.00(12) . . ? C4 C5 C6 123.49(13) . . ? N2 C6 C5 121.27(13) . . ? O1 C7 N3 122.35(13) . . ? O1 C7 C8 120.88(13) . . ? N3 C7 C8 116.77(12) . . ? C12 C8 C9 117.25(13) . . ? C12 C8 C7 117.34(13) . . ? C9 C8 C7 125.41(13) . . ? C10 C9 C8 119.04(15) . . ? C11 C10 C9 119.24(15) . . ? N4 C11 C10 123.52(15) . . ? N4 C12 C8 124.16(15) . . ? C1 N1 C5 117.39(13) . . ? C6 N2 N3 115.80(11) . . ? C7 N3 N2 118.26(11) . . ? C11 N4 C12 116.78(14) . . ? #===END # HPCPH # CIF produced by WinGX routine CIF_UPDATE # Created on 2007-03-16 at 15:04:42 # Using CIFtbx version 2.6.2 16 Jun 1998 # Dictionary name : cif_core.dic # Dictionary vers : 2.3 # Request file : c:\wingx\files\archive.dat # CIF files read : 2046ac39 dreduc psi_scan struct data_2046ac39 _database_code_depnum_ccdc_archive 'CCDC 640840' _audit_creation_date 2007-03-16T15:04:42-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.3 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C12 H10 N4 O1' _chemical_formula_sum 'C12 H10 N4 O' _chemical_formula_weight 226.24 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/n' _symmetry_space_group_name_Hall '-P 2yn' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 8.4690(10) _cell_length_b 13.836(2) _cell_length_c 9.806(2) _cell_angle_alpha 90 _cell_angle_beta 105.640(10) _cell_angle_gamma 90 _cell_volume 1106.5(3) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 24 _cell_measurement_theta_min 10.252 _cell_measurement_theta_max 14.255 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.5 _exptl_crystal_size_mid 0.4 _exptl_crystal_size_min 0.3 _exptl_crystal_density_diffrn 1.358 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 472 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.092 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_process_details ; North A.C.T., Phillips D.C. & Mathews F.S. (1968) Acta. Cryst. A24, 351 Number of psi-scan sets used was 4 Theta correction was applied. Averaged transmission function was used. No Fourier smoothing was applied. ; _exptl_absorpt_correction_T_min 0.9027 _exptl_absorpt_correction_T_max 0.9678 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_source 'Enraf Nonius FR590' _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_detector 'scintillation LiI' _diffrn_detector_dtime 1.195 _diffrn_orient_matrix_type ; x-axis points to radiation source the matrix is specified in reciprocal space ; _diffrn_orient_matrix_ub_11 -0.070896 _diffrn_orient_matrix_ub_12 0.051 _diffrn_orient_matrix_ub_13 -0.05822 _diffrn_orient_matrix_ub_21 -0.058275 _diffrn_orient_matrix_ub_22 -0.050527 _diffrn_orient_matrix_ub_23 -0.068003 _diffrn_orient_matrix_ub_31 -0.081359 _diffrn_orient_matrix_ub_32 -0.008254 _diffrn_orient_matrix_ub_33 0.056506 _diffrn_measurement_device '\k-geometry diffractometer' _diffrn_measurement_device_type 'Enraf Nonius TurboCAD4' _diffrn_measurement_method 'non-profiled omega/2theta scans' _diffrn_standards_number 3 _diffrn_standards_interval_time 120 _diffrn_standards_decay_% -1 loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l -3 2 -3 1 -9 0 -3 -2 4 _diffrn_reflns_av_R_equivalents 0.0262 _diffrn_reflns_av_unetI/netI 0.0316 _diffrn_reflns_number 2077 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.61 _diffrn_reflns_theta_max 24.98 _diffrn_reflns_theta_full 24.98 _diffrn_measured_fraction_theta_full 1 _diffrn_measured_fraction_theta_max 1 _reflns_number_total 1941 _reflns_number_gt 1127 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'CAD4 Express (Enraf Nonius, 1994)' _computing_cell_refinement 'CAD4 Express (Enraf Nonius, 1994)' _computing_data_reduction 'XCAD4 (Harms & Wocadlo, 1995)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.0684P)^2^+0.0222P] 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_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_coef 0.013(2) _refine_ls_number_reflns 1941 _refine_ls_number_parameters 155 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0924 _refine_ls_R_factor_gt 0.04 _refine_ls_wR_factor_ref 0.1236 _refine_ls_wR_factor_gt 0.102 _refine_ls_goodness_of_fit_ref 1.012 _refine_ls_restrained_S_all 1.012 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.147 _refine_diff_density_min -0.149 _refine_diff_density_rms 0.039 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 C1 C 0.9818(3) 0.76419(16) 1.0308(2) 0.0623(6) Uani 1 1 d . . . H1 H 1.0876 0.7833 1.0786 0.075 Uiso 1 1 calc R . . C2 C 0.8701(3) 0.83469(16) 0.9769(2) 0.0662(6) Uani 1 1 d . . . H2 H 0.899 0.8996 0.9882 0.079 Uiso 1 1 calc R . . C3 C 0.7142(3) 0.80756(15) 0.9057(2) 0.0655(6) Uani 1 1 d . . . H3 H 0.6353 0.8539 0.867 0.079 Uiso 1 1 calc R . . C4 C 0.6762(2) 0.71156(15) 0.8923(2) 0.0551(6) Uani 1 1 d . . . H4 H 0.571 0.6916 0.8446 0.066 Uiso 1 1 calc R . . C5 C 0.7966(2) 0.64416(14) 0.9507(2) 0.0465(5) Uani 1 1 d . . . C6 C 0.7644(2) 0.54039(14) 0.9385(2) 0.0514(5) Uani 1 1 d . . . H6 H 0.8466 0.4971 0.9819 0.062 Uiso 1 1 calc R . . C7 C 0.4617(2) 0.37105(14) 0.7898(2) 0.0518(5) Uani 1 1 d . . . C8 C 0.4542(2) 0.26375(13) 0.79961(19) 0.0449(5) Uani 1 1 d . . . C9 C 0.3115(2) 0.21697(14) 0.7319(2) 0.0528(5) Uani 1 1 d . . . H9 H 0.2214 0.2516 0.6794 0.063 Uiso 1 1 calc R . . C10 C 0.3041(2) 0.11825(15) 0.7430(2) 0.0561(6) Uani 1 1 d . . . H10 H 0.2087 0.0848 0.699 0.067 Uiso 1 1 calc R . . C11 C 0.4401(2) 0.07009(15) 0.8202(2) 0.0601(6) Uani 1 1 d . . . H11 H 0.4391 0.0032 0.8291 0.072 Uiso 1 1 calc R . . C12 C 0.5781(2) 0.12223(15) 0.8843(2) 0.0627(6) Uani 1 1 d . . . H12 H 0.6697 0.0887 0.9365 0.075 Uiso 1 1 calc R . . N1 N 0.94996(19) 0.66965(12) 1.01979(18) 0.0568(5) Uani 1 1 d . . . N2 N 0.62527(19) 0.50881(11) 0.86919(16) 0.0524(5) Uani 1 1 d . . . N3 N 0.60548(19) 0.41067(11) 0.86554(17) 0.0538(5) Uani 1 1 d . . . H3A H 0.684 0.374 0.9112 0.065 Uiso 1 1 calc R . . N4 N 0.58828(19) 0.21839(12) 0.87608(17) 0.0544(5) Uani 1 1 d . . . O1 O 0.34817(18) 0.41829(10) 0.72022(18) 0.0789(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 C1 0.0524(13) 0.0627(15) 0.0696(15) -0.0079(12) 0.0129(11) -0.0133(11) C2 0.0697(15) 0.0519(13) 0.0823(16) -0.0088(12) 0.0295(13) -0.0101(12) C3 0.0627(15) 0.0511(13) 0.0847(16) 0.0029(12) 0.0235(13) 0.0063(11) C4 0.0434(11) 0.0559(13) 0.0630(13) 0.0011(10) 0.0095(10) 0.0023(9) C5 0.0394(11) 0.0502(12) 0.0489(11) 0.0029(9) 0.0103(9) -0.0025(9) C6 0.0404(11) 0.0492(12) 0.0603(13) 0.0047(10) 0.0058(9) 0.0009(9) C7 0.0449(11) 0.0468(11) 0.0596(13) -0.0061(10) 0.0068(10) 0.0035(9) C8 0.0372(10) 0.0482(11) 0.0476(11) -0.0016(9) 0.0083(9) 0.0016(8) C9 0.0411(11) 0.0539(12) 0.0583(13) 0.0006(10) 0.0046(10) -0.0007(10) C10 0.0481(12) 0.0547(13) 0.0612(14) -0.0004(10) 0.0077(10) -0.0090(10) C11 0.0567(14) 0.0453(11) 0.0758(15) 0.0050(11) 0.0135(11) -0.0047(10) C12 0.0466(12) 0.0490(13) 0.0847(17) 0.0123(11) 0.0039(12) 0.0033(10) N1 0.0437(10) 0.0555(10) 0.0671(11) 0.0009(9) 0.0078(8) -0.0065(8) N2 0.0476(10) 0.0428(9) 0.0619(11) -0.0026(8) 0.0064(8) 0.0003(8) N3 0.0446(10) 0.0411(9) 0.0677(12) -0.0010(8) 0.0011(8) 0.0008(8) N4 0.0421(10) 0.0497(10) 0.0653(12) 0.0039(8) 0.0038(8) 0.0023(8) O1 0.0557(10) 0.0493(9) 0.1104(14) -0.0047(8) -0.0145(9) 0.0106(7) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 C1 N1 1.334(2) . ? C1 C2 1.363(3) . ? C2 C3 1.369(3) . ? C3 C4 1.365(3) . ? C4 C5 1.386(3) . ? C5 N1 1.340(2) . ? C5 C6 1.460(3) . ? C6 N2 1.269(2) . ? C7 O1 1.210(2) . ? C7 N3 1.359(2) . ? C7 C8 1.490(3) . ? C8 N4 1.337(2) . ? C8 C9 1.374(2) . ? C9 C10 1.373(3) . ? C10 C11 1.369(3) . ? C11 C12 1.373(3) . ? C12 N4 1.337(3) . ? N2 N3 1.367(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 C1 C2 124.5(2) . . ? C1 C2 C3 118.4(2) . . ? C4 C3 C2 119.1(2) . . ? C3 C4 C5 119.15(19) . . ? N1 C5 C4 122.44(18) . . ? N1 C5 C6 115.71(18) . . ? C4 C5 C6 121.84(18) . . ? N2 C6 C5 120.54(18) . . ? O1 C7 N3 123.30(18) . . ? O1 C7 C8 122.25(18) . . ? N3 C7 C8 114.45(17) . . ? N4 C8 C9 123.61(18) . . ? N4 C8 C7 117.35(17) . . ? C9 C8 C7 119.03(17) . . ? C10 C9 C8 118.91(18) . . ? C11 C10 C9 118.59(19) . . ? C10 C11 C12 118.87(19) . . ? N4 C12 C11 123.80(19) . . ? C1 N1 C5 116.50(18) . . ? C6 N2 N3 116.46(16) . . ? C7 N3 N2 120.01(16) . . ? C8 N4 C12 116.23(17) . . ? #===END # HPC2BBH # CIF produced by WinGX routine CIF_UPDATE # Created on 2007-03-16 at 15:09:10 # Using CIFtbx version 2.6.2 16 Jun 1998 # Dictionary name : cif_core.dic # Dictionary vers : 2.3 # Request file : c:\wingx\files\archive.dat # CIF files read : 2030ac30 dreduc psi_scan struct data_2030ac30 _database_code_depnum_ccdc_archive 'CCDC 640841' _audit_creation_date 2007-03-16T15:09:10-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.3 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C13 H10 Br1 N3 O, 2(H2 O)' _chemical_formula_sum 'C13 H14 Br N3 O3' _chemical_formula_weight 340.18 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting trigonal _symmetry_space_group_name_H-M 'R -3' _symmetry_space_group_name_Hall '-R 3' _symmetry_Int_Tables_number 148 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z' '-x+y, -x, z' 'x+2/3, y+1/3, z+1/3' '-y+2/3, x-y+1/3, z+1/3' '-x+y+2/3, -x+1/3, z+1/3' 'x+1/3, y+2/3, z+2/3' '-y+1/3, x-y+2/3, z+2/3' '-x+y+1/3, -x+2/3, z+2/3' '-x, -y, -z' 'y, -x+y, -z' 'x-y, x, -z' '-x+2/3, -y+1/3, -z+1/3' 'y+2/3, -x+y+1/3, -z+1/3' 'x-y+2/3, x+1/3, -z+1/3' '-x+1/3, -y+2/3, -z+2/3' 'y+1/3, -x+y+2/3, -z+2/3' 'x-y+1/3, x+2/3, -z+2/3' _cell_length_a 26.311(3) _cell_length_b 26.311(3) _cell_length_c 11.2700(10) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 120 _cell_volume 6756.6(12) _cell_formula_units_Z 18 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 10.354 _cell_measurement_theta_max 14.108 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.5 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.1 _exptl_crystal_density_diffrn 1.505 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 3096 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 2.748 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_process_details ; North A.C.T., Phillips D.C. & Mathews F.S. (1968) Acta. Cryst. A24, 351 Number of psi-scan sets used was 4 Theta correction was applied. Averaged transmission function was used. No Fourier smoothing was applied. ; _exptl_absorpt_correction_T_min 0.6918 _exptl_absorpt_correction_T_max 0.759 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_source 'Enraf Nonius FR590' _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_detector 'scintillation LiI' _diffrn_detector_dtime 1.195 _diffrn_orient_matrix_type ; x-axis points to radiation source the matrix is specified in reciprocal space ; _diffrn_orient_matrix_ub_11 0.041174 _diffrn_orient_matrix_ub_12 0.031712 _diffrn_orient_matrix_ub_13 -0.016197 _diffrn_orient_matrix_ub_21 -0.014206 _diffrn_orient_matrix_ub_22 0.028241 _diffrn_orient_matrix_ub_23 -0.015408 _diffrn_orient_matrix_ub_31 0.005193 _diffrn_orient_matrix_ub_32 0.011012 _diffrn_orient_matrix_ub_33 0.08593 _diffrn_measurement_device '\k-geometry diffractometer' _diffrn_measurement_device_type 'Enraf Nonius TurboCAD4' _diffrn_measurement_method 'non-profiled omega/2theta scans' _diffrn_standards_number 3 _diffrn_standards_interval_time 120 _diffrn_standards_decay_% -5 loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l -12 13 -1 -12 -1 1 0 7 5 _diffrn_reflns_av_R_equivalents 0.0801 _diffrn_reflns_av_unetI/netI 0.243 _diffrn_reflns_number 3237 _diffrn_reflns_limit_h_min -1 _diffrn_reflns_limit_h_max 27 _diffrn_reflns_limit_k_min -1 _diffrn_reflns_limit_k_max 27 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 1.55 _diffrn_reflns_theta_max 24.98 _diffrn_reflns_theta_full 24.98 _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _reflns_number_total 2639 _reflns_number_gt 787 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'CAD4 Express (Enraf Nonius, 1994)' _computing_cell_refinement 'CAD4 Express (Enraf Nonius, 1994)' _computing_data_reduction 'XCAD4 (Harms & Wocadlo, 1995)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.0315P)^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_number_reflns 2639 _refine_ls_number_parameters 181 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.2601 _refine_ls_R_factor_gt 0.0477 _refine_ls_wR_factor_ref 0.1179 _refine_ls_wR_factor_gt 0.0766 _refine_ls_goodness_of_fit_ref 0.927 _refine_ls_restrained_S_all 0.927 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.352 _refine_diff_density_min -0.304 _refine_diff_density_rms 0.072 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 C1 C 0.4142(3) -0.1177(3) 0.5646(7) 0.052(2) Uani 1 1 d . . . H1 H 0.3861 -0.1313 0.6244 0.063 Uiso 1 1 calc R . . C2 C 0.4512(3) -0.1400(3) 0.5582(7) 0.056(2) Uani 1 1 d . . . H2 H 0.4478 -0.1688 0.6109 0.067 Uiso 1 1 calc R . . C3 C 0.4936(3) -0.1188(3) 0.4713(7) 0.057(2) Uani 1 1 d . . . H3 H 0.5191 -0.1335 0.4636 0.069 Uiso 1 1 calc R . . C4 C 0.4979(3) -0.0763(3) 0.3970(7) 0.049(2) Uani 1 1 d . . . H4 H 0.5275 -0.0602 0.3403 0.058 Uiso 1 1 calc R . . C5 C 0.4580(3) -0.0571(3) 0.4063(6) 0.0342(18) Uani 1 1 d . . . C6 C 0.4565(3) -0.0143(3) 0.3291(7) 0.040(2) Uani 1 1 d . . . H6 H 0.4269 -0.0051 0.3373 0.047 Uiso 1 1 calc R . . C7 C 0.5327(4) 0.0836(3) 0.0993(7) 0.046(2) Uani 1 1 d . . . C8 C 0.5165(3) 0.1201(3) 0.0233(6) 0.042(2) Uani 1 1 d . . . C9 C 0.5471(3) 0.1807(4) 0.0261(6) 0.051(2) Uani 1 1 d . . . C10 C 0.5341(4) 0.2135(4) -0.0505(8) 0.072(3) Uani 1 1 d . . . H10 H 0.5555 0.2543 -0.0478 0.086 Uiso 1 1 calc R . . C11 C 0.4898(4) 0.1856(5) -0.1301(7) 0.071(3) Uani 1 1 d . . . H11 H 0.4808 0.2073 -0.1823 0.085 Uiso 1 1 calc R . . C12 C 0.4586(4) 0.1258(5) -0.1334(7) 0.069(3) Uani 1 1 d . . . H12 H 0.4282 0.1071 -0.1881 0.083 Uiso 1 1 calc R . . C13 C 0.4711(3) 0.0926(3) -0.0574(7) 0.056(2) Uani 1 1 d . . . H13 H 0.4492 0.0518 -0.0603 0.068 Uiso 1 1 calc R . . Br1 Br 0.60900(4) 0.22240(4) 0.13622(9) 0.0830(4) Uani 1 1 d . . . N1 N 0.4161(2) -0.0774(2) 0.4901(5) 0.0414(15) Uani 1 1 d . . . N2 N 0.4961(2) 0.0112(2) 0.2491(5) 0.0420(16) Uani 1 1 d . . . N3 N 0.4897(2) 0.0502(2) 0.1784(5) 0.0446(16) Uani 1 1 d . . . H3A H 0.4589 0.0534 0.184 0.053 Uiso 1 1 calc R . . O1 O 0.5785(2) 0.0836(2) 0.0894(5) 0.0681(17) Uani 1 1 d . . . O2 O 0.38068(17) 0.04746(17) 0.2194(4) 0.0558(14) Uani 1 1 d . . . H21 H 0.346 0.0214 0.1966 0.084 Uiso 1 1 d R . . H22 H 0.3855 0.0796 0.1905 0.084 Uiso 1 1 d R . . O3 O 0.63226(19) 0.02351(19) 0.2082(4) 0.0727(16) Uani 1 1 d . . . H31 H 0.6095 0.0365 0.1862 0.109 Uiso 1 1 d R . . H32 H 0.6395 0.0326 0.2805 0.109 Uiso 1 1 d 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 C1 0.059(6) 0.050(5) 0.051(6) 0.011(5) 0.004(4) 0.030(5) C2 0.080(7) 0.046(5) 0.055(6) 0.018(5) 0.008(5) 0.041(5) C3 0.053(6) 0.062(6) 0.075(7) 0.006(5) -0.002(5) 0.042(5) C4 0.045(5) 0.044(5) 0.059(6) 0.004(4) 0.003(4) 0.023(4) C5 0.038(5) 0.031(4) 0.036(5) 0.010(4) 0.001(4) 0.019(4) C6 0.037(5) 0.027(4) 0.049(6) 0.000(4) 0.008(4) 0.012(4) C7 0.048(6) 0.041(5) 0.046(5) 0.021(4) 0.010(5) 0.019(5) C8 0.040(5) 0.047(5) 0.048(6) 0.016(5) 0.018(4) 0.029(4) C9 0.050(5) 0.059(6) 0.045(5) 0.010(5) 0.006(4) 0.029(5) C10 0.070(7) 0.073(7) 0.082(7) 0.034(6) 0.013(6) 0.043(6) C11 0.092(8) 0.107(9) 0.051(7) 0.032(7) 0.011(6) 0.077(8) C12 0.068(7) 0.113(9) 0.042(6) 0.009(6) -0.003(5) 0.058(7) C13 0.056(6) 0.068(6) 0.048(6) 0.000(5) -0.006(5) 0.033(5) Br1 0.0684(7) 0.0646(7) 0.1054(7) -0.0026(6) -0.0161(7) 0.0253(6) N1 0.046(4) 0.037(4) 0.043(4) 0.010(3) 0.006(3) 0.022(3) N2 0.039(4) 0.037(4) 0.050(5) 0.010(3) -0.002(4) 0.018(3) N3 0.046(4) 0.047(4) 0.051(4) 0.009(3) 0.001(4) 0.031(4) O1 0.051(4) 0.093(4) 0.075(4) 0.035(3) 0.022(3) 0.046(3) O2 0.050(3) 0.050(3) 0.067(4) 0.004(3) -0.008(3) 0.025(3) O3 0.068(4) 0.096(4) 0.077(4) -0.016(3) -0.010(3) 0.058(4) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 C1 N1 1.334(7) . ? C1 C2 1.369(8) . ? C2 C3 1.374(9) . ? C3 C4 1.357(9) . ? C4 C5 1.376(8) . ? C5 N1 1.342(7) . ? C5 C6 1.439(8) . ? C6 N2 1.283(7) . ? C7 O1 1.210(7) . ? C7 N3 1.360(8) . ? C7 C8 1.499(9) . ? C8 C9 1.381(9) . ? C8 C13 1.384(9) . ? C9 C10 1.379(9) . ? C9 Br1 1.900(7) . ? C10 C11 1.359(10) . ? C11 C12 1.365(10) . ? C12 C13 1.377(9) . ? N2 N3 1.374(6) . ? 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 C1 C2 123.8(7) . . ? C1 C2 C3 118.0(7) . . ? C4 C3 C2 119.4(7) . . ? C3 C4 C5 119.4(7) . . ? N1 C5 C4 122.3(7) . . ? N1 C5 C6 113.4(6) . . ? C4 C5 C6 124.3(7) . . ? N2 C6 C5 120.1(7) . . ? O1 C7 N3 124.4(7) . . ? O1 C7 C8 123.3(7) . . ? N3 C7 C8 112.2(7) . . ? C9 C8 C13 118.1(7) . . ? C9 C8 C7 122.6(7) . . ? C13 C8 C7 119.2(7) . . ? C10 C9 C8 121.7(7) . . ? C10 C9 Br1 117.1(7) . . ? C8 C9 Br1 121.2(6) . . ? C11 C10 C9 119.2(8) . . ? C10 C11 C12 120.1(8) . . ? C11 C12 C13 121.2(9) . . ? C12 C13 C8 119.7(8) . . ? C1 N1 C5 117.1(6) . . ? C6 N2 N3 115.4(6) . . ? C7 N3 N2 119.4(6) . . ? #===END # HPC3HH # CIF produced by WinGX routine CIF_UPDATE # Created on 2007-03-16 at 15:12:52 # Using CIFtbx version 2.6.2 16 Jun 1998 # Dictionary name : cif_core.dic # Dictionary vers : 2.3 # Request file : c:\wingx\files\archive.dat # CIF files read : ac44345 dreduc psi_scan struct data_ac44345 _database_code_depnum_ccdc_archive 'CCDC 640842' _audit_creation_date 2007-03-16T15:12:52-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.3 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C13 H11 N3 O2' _chemical_formula_sum 'C13 H11 N3 O2' _chemical_formula_weight 241.25 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_Int_Tables_number 14 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 4.6180(10) _cell_length_b 22.759(3) _cell_length_c 10.663(3) _cell_angle_alpha 90 _cell_angle_beta 96.98(2) _cell_angle_gamma 90 _cell_volume 1112.4(4) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 23 _cell_measurement_theta_min 8.501 _cell_measurement_theta_max 15.382 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.13 _exptl_crystal_density_diffrn 1.441 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 504 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.101 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_process_details ; North A.C.T., Phillips D.C. & Mathews F.S. (1968) Acta. Cryst. A24, 351 Number of psi-scan sets used was 3 Theta correction was applied. Averaged transmission function was used. No Fourier smoothing was applied. ; _exptl_absorpt_correction_T_min 0.451 _exptl_absorpt_correction_T_max 0.6196 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_source 'Enraf Nonius FR590' _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_detector 'scintillation LiI' _diffrn_detector_dtime 1.195 _diffrn_orient_matrix_type ; x-axis points to radiation source the matrix is specified in reciprocal space ; _diffrn_orient_matrix_ub_11 -0.212604 _diffrn_orient_matrix_ub_12 0.008297 _diffrn_orient_matrix_ub_13 -0.022744 _diffrn_orient_matrix_ub_21 0.039445 _diffrn_orient_matrix_ub_22 0.043075 _diffrn_orient_matrix_ub_23 0.009506 _diffrn_orient_matrix_ub_31 0.0297 _diffrn_orient_matrix_ub_32 0.002393 _diffrn_orient_matrix_ub_33 -0.091224 _diffrn_measurement_device '\k-geometry diffractometer' _diffrn_measurement_device_type 'Enraf Nonius CAD4' _diffrn_measurement_method 'non-profiled omega/2theta scans' _diffrn_standards_number 3 _diffrn_standards_interval_time 120 _diffrn_standards_decay_% 1 loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l -2 9 0 1 1 -5 0 4 -4 _diffrn_reflns_av_R_equivalents 0.0559 _diffrn_reflns_av_unetI/netI 0.1062 _diffrn_reflns_number 2217 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 27 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 1.79 _diffrn_reflns_theta_max 24.96 _diffrn_reflns_theta_full 24.96 _diffrn_measured_fraction_theta_full 1 _diffrn_measured_fraction_theta_max 1 _reflns_number_total 1964 _reflns_number_gt 854 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'CAD4 Express (Enraf Nonius, 1994)' _computing_cell_refinement 'CAD4 Express (Enraf Nonius, 1994)' _computing_data_reduction 'XCAD4 (Harms & Wocadlo, 1995)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.0736P)^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_number_reflns 1964 _refine_ls_number_parameters 163 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1686 _refine_ls_R_factor_gt 0.0494 _refine_ls_wR_factor_ref 0.1589 _refine_ls_wR_factor_gt 0.1151 _refine_ls_goodness_of_fit_ref 0.956 _refine_ls_restrained_S_all 0.956 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.271 _refine_diff_density_min -0.215 _refine_diff_density_rms 0.059 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 C1 C 0.5111(9) 0.03188(18) 0.3048(4) 0.0488(12) Uani 1 1 d . . . H1 H 0.4751 0.007 0.3702 0.059 Uiso 1 1 calc R . . C2 C 0.3622(9) 0.02276(18) 0.1893(4) 0.0470(11) Uani 1 1 d . . . H2 H 0.228 -0.0077 0.1757 0.056 Uiso 1 1 calc R . . C3 C 0.4137(8) 0.05951(18) 0.0925(4) 0.0437(11) Uani 1 1 d . . . H3 H 0.3145 0.0542 0.012 0.052 Uiso 1 1 calc R . . C4 C 0.6140(8) 0.10455(18) 0.1152(4) 0.0385(10) Uani 1 1 d . . . H4 H 0.6504 0.1301 0.0509 0.046 Uiso 1 1 calc R . . C5 C 0.7583(8) 0.11070(16) 0.2351(3) 0.0327(9) Uani 1 1 d . . . C6 C 0.9758(8) 0.15630(17) 0.2697(4) 0.0363(10) Uani 1 1 d . . . H6 H 1.0444 0.1631 0.3541 0.044 Uiso 1 1 calc R . . C7 C 1.3908(8) 0.26284(16) 0.1356(4) 0.0331(9) Uani 1 1 d . . . C8 C 1.6184(8) 0.30608(15) 0.1884(3) 0.0309(9) Uani 1 1 d . . . C9 C 1.6994(8) 0.34851(17) 0.1052(4) 0.0360(10) Uani 1 1 d . . . H9 H 1.6069 0.35 0.0227 0.043 Uiso 1 1 calc R . . C10 C 1.9164(8) 0.38835(16) 0.1447(4) 0.0356(10) Uani 1 1 d . . . C11 C 2.0546(8) 0.38606(17) 0.2659(3) 0.0363(10) Uani 1 1 d . . . H11 H 2.2036 0.4125 0.2917 0.044 Uiso 1 1 calc R . . C12 C 1.9743(8) 0.34509(16) 0.3492(4) 0.0366(10) Uani 1 1 d . . . H12 H 2.0683 0.3441 0.4315 0.044 Uiso 1 1 calc R . . C13 C 1.7536(8) 0.30506(16) 0.3118(4) 0.0365(10) Uani 1 1 d . . . H13 H 1.697 0.2778 0.3691 0.044 Uiso 1 1 calc R . . N1 N 0.7081(7) 0.07496(14) 0.3301(3) 0.0407(9) Uani 1 1 d . . . N2 N 1.0710(6) 0.18690(13) 0.1828(3) 0.0355(8) Uani 1 1 d . . . N3 N 1.2766(6) 0.22883(14) 0.2223(3) 0.0364(8) Uani 1 1 d . . . H3A H 1.3327 0.2335 0.3015 0.044 Uiso 1 1 calc R . . O1 O 1.3155(6) 0.25774(12) 0.0226(2) 0.0466(8) Uani 1 1 d . . . O2 O 2.0076(6) 0.43009(12) 0.0676(2) 0.0609(9) Uani 1 1 d . . . H2A H 1.9119 0.4278 -0.0022 0.091 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 C1 0.065(3) 0.034(3) 0.048(3) 0.005(2) 0.008(2) -0.011(2) C2 0.047(3) 0.032(2) 0.060(3) 0.000(2) 0.000(2) -0.013(2) C3 0.045(2) 0.040(2) 0.043(2) -0.007(2) -0.005(2) 0.000(2) C4 0.046(2) 0.036(2) 0.035(2) 0.0039(19) 0.0072(19) -0.001(2) C5 0.036(2) 0.028(2) 0.037(2) -0.0008(18) 0.0122(19) 0.0025(18) C6 0.039(2) 0.036(2) 0.035(2) -0.0022(19) 0.0048(19) 0.000(2) C7 0.035(2) 0.030(2) 0.035(2) -0.0014(19) 0.0055(18) 0.0015(18) C8 0.034(2) 0.023(2) 0.038(2) -0.0045(17) 0.0103(18) 0.0025(17) C9 0.035(2) 0.034(2) 0.039(2) -0.0048(19) 0.0057(18) 0.003(2) C10 0.042(2) 0.026(2) 0.039(2) 0.0024(19) 0.010(2) 0.0002(19) C11 0.035(2) 0.033(2) 0.040(2) -0.0068(19) 0.0025(19) -0.0023(19) C12 0.041(2) 0.032(2) 0.037(2) -0.006(2) 0.0042(18) 0.0034(19) C13 0.037(2) 0.035(2) 0.039(2) -0.0008(18) 0.0074(19) 0.003(2) N1 0.046(2) 0.037(2) 0.0387(19) 0.0002(17) 0.0042(16) -0.0048(17) N2 0.0303(18) 0.0306(19) 0.046(2) -0.0061(16) 0.0058(16) -0.0023(16) N3 0.0351(18) 0.0346(19) 0.0394(19) -0.0049(16) 0.0043(15) -0.0025(16) O1 0.0542(18) 0.0438(18) 0.0411(16) -0.0037(14) 0.0025(13) -0.0133(15) O2 0.078(2) 0.053(2) 0.0485(17) 0.0112(16) -0.0050(16) -0.0275(18) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 C1 N1 1.342(5) . ? C1 C2 1.352(5) . ? C2 C3 1.372(5) . ? C3 C4 1.382(5) . ? C4 C5 1.375(5) . ? C5 N1 1.341(4) . ? C5 C6 1.460(5) . ? C6 N2 1.279(4) . ? C7 O1 1.218(4) . ? C7 N3 1.360(4) . ? C7 C8 1.499(5) . ? C8 C13 1.386(5) . ? C8 C9 1.393(5) . ? C9 C10 1.379(5) . ? C10 O2 1.356(4) . ? C10 C11 1.371(5) . ? C11 C12 1.370(5) . ? C12 C13 1.389(5) . ? N2 N3 1.376(4) . ? 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 C1 C2 123.6(4) . . ? C1 C2 C3 118.5(4) . . ? C2 C3 C4 119.6(4) . . ? C5 C4 C3 118.5(4) . . ? N1 C5 C4 122.1(4) . . ? N1 C5 C6 114.7(3) . . ? C4 C5 C6 123.2(4) . . ? N2 C6 C5 119.4(4) . . ? O1 C7 N3 122.0(3) . . ? O1 C7 C8 122.5(4) . . ? N3 C7 C8 115.5(3) . . ? C13 C8 C9 119.4(3) . . ? C13 C8 C7 124.1(3) . . ? C9 C8 C7 116.5(3) . . ? C10 C9 C8 120.2(4) . . ? O2 C10 C11 117.0(4) . . ? O2 C10 C9 122.9(4) . . ? C11 C10 C9 120.1(4) . . ? C12 C11 C10 120.4(4) . . ? C11 C12 C13 120.5(4) . . ? C8 C13 C12 119.5(4) . . ? C5 N1 C1 117.8(3) . . ? C6 N2 N3 116.2(3) . . ? C7 N3 N2 119.8(3) . . ? #===END # H2PC3BBH.ClO4.2H2O # CIF produced by WinGX routine CIF_UPDATE # Created on 2007-03-16 at 15:16:25 # Using CIFtbx version 2.6.2 16 Jun 1998 # Dictionary name : cif_core.dic # Dictionary vers : 2.3 # Request file : c:\wingx\files\archive.dat # CIF files read : 2049ac43 dreduc psi_scan struct data_2049ac43 _database_code_depnum_ccdc_archive 'CCDC 640843' _audit_creation_date 2007-03-16T15:16:25-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.3 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C13 H11 Br1 N3 O, Cl O4, 2(H2 O))' _chemical_formula_sum 'C13 H15 Br Cl N3 O7' _chemical_formula_weight 440.64 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_Int_Tables_number 14 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 6.839(5) _cell_length_b 16.527(5) _cell_length_c 15.507(5) _cell_angle_alpha 90 _cell_angle_beta 90.079(5) _cell_angle_gamma 90 _cell_volume 1752.7(15) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 10.135 _cell_measurement_theta_max 14.234 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.5 _exptl_crystal_size_mid 0.5 _exptl_crystal_size_min 0.5 _exptl_crystal_density_diffrn 1.67 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 888 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 2.538 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_process_details ; North A.C.T., Phillips D.C. & Mathews F.S. (1968) Acta. Cryst. A24, 351 Number of psi-scan sets used was 5 Theta correction was applied. Averaged transmission function was used. No Fourier smoothing was applied. ; _exptl_absorpt_correction_T_min 0.7669 _exptl_absorpt_correction_T_max 0.8843 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_source 'Enraf Nonius FR590' _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_detector 'scintillation LiI' _diffrn_detector_dtime 1.195 _diffrn_orient_matrix_type ; x-axis points to radiation source the matrix is specified in reciprocal space ; _diffrn_orient_matrix_ub_11 0.108239 _diffrn_orient_matrix_ub_12 -0.017424 _diffrn_orient_matrix_ub_13 0.039227 _diffrn_orient_matrix_ub_21 -0.00943 _diffrn_orient_matrix_ub_22 -0.056252 _diffrn_orient_matrix_ub_23 -0.023385 _diffrn_orient_matrix_ub_31 0.097873 _diffrn_orient_matrix_ub_32 0.013887 _diffrn_orient_matrix_ub_33 -0.045533 _diffrn_measurement_device '\k-geometry diffractometer' _diffrn_measurement_device_type 'Enraf Nonius TurboCAD4' _diffrn_measurement_method 'non-profiled omega/2theta scans' _diffrn_standards_number 3 _diffrn_standards_interval_time 120 _diffrn_standards_decay_% -3 loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l 3 -4 5 0 -9 -3 2 2 -8 _diffrn_reflns_av_R_equivalents 0.0264 _diffrn_reflns_av_unetI/netI 0.0325 _diffrn_reflns_number 3356 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.8 _diffrn_reflns_theta_max 24.97 _diffrn_reflns_theta_full 24.97 _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _reflns_number_total 3082 _reflns_number_gt 1991 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'CAD4 Express (Enraf Nonius, 1994)' _computing_cell_refinement 'CAD4 Express (Enraf Nonius, 1994)' _computing_data_reduction 'XCAD4 (Harms & Wocadlo, 1995)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.0574P)^2^+1.2660P] 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_number_reflns 3082 _refine_ls_number_parameters 226 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.08 _refine_ls_R_factor_gt 0.0405 _refine_ls_wR_factor_ref 0.1157 _refine_ls_wR_factor_gt 0.1 _refine_ls_goodness_of_fit_ref 1.018 _refine_ls_restrained_S_all 1.018 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.48 _refine_diff_density_min -0.404 _refine_diff_density_rms 0.082 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 '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 0.006 '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' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 C1 C -0.6626(7) 0.0635(3) 1.1506(3) 0.0770(14) Uani 1 1 d . . . H1 H -0.6498 0.0075 1.15 0.092 Uiso 1 1 calc R . . C2 C -0.8230(7) 0.0987(4) 1.1878(3) 0.0864(17) Uani 1 1 d . . . H2 H -0.9201 0.0668 1.2124 0.104 Uiso 1 1 calc R . . C3 C -0.8387(7) 0.1804(4) 1.1885(3) 0.0794(15) Uani 1 1 d . . . H3 H -0.9467 0.205 1.2138 0.095 Uiso 1 1 calc R . . C4 C -0.6957(6) 0.2265(3) 1.1520(3) 0.0628(12) Uani 1 1 d . . . H4 H -0.7061 0.2826 1.1529 0.075 Uiso 1 1 calc R . . C5 C -0.5367(6) 0.1908(2) 1.1140(2) 0.0488(10) Uani 1 1 d . . . C6 C -0.3807(6) 0.2371(3) 1.0737(2) 0.0507(10) Uani 1 1 d . . . H6 H -0.3841 0.2933 1.0725 0.061 Uiso 1 1 calc R . . C7 C 0.0522(6) 0.1986(2) 0.9650(2) 0.0486(9) Uani 1 1 d . . . C8 C 0.2168(5) 0.2449(2) 0.9250(2) 0.0475(9) Uani 1 1 d . . . C9 C 0.3567(6) 0.2003(2) 0.8807(2) 0.0496(10) Uani 1 1 d . . . H9 H 0.3415 0.1447 0.8741 0.06 Uiso 1 1 calc R . . C10 C 0.5176(6) 0.2386(3) 0.8468(2) 0.0521(10) Uani 1 1 d . . . C11 C 0.5412(6) 0.3214(3) 0.8549(3) 0.0624(11) Uani 1 1 d . . . H11 H 0.65 0.3469 0.8313 0.075 Uiso 1 1 calc R . . C12 C 0.4020(6) 0.3656(3) 0.8980(3) 0.0663(12) Uani 1 1 d . . . H12 H 0.4164 0.4213 0.9036 0.08 Uiso 1 1 calc R . . C13 C 0.2405(6) 0.3275(3) 0.9331(3) 0.0605(11) Uani 1 1 d . . . H13 H 0.1472 0.3577 0.9624 0.073 Uiso 1 1 calc R . . N1 N -0.5251(5) 0.1098(2) 1.1152(2) 0.0571(9) Uani 1 1 d . . . H1A H -0.425 0.0869 1.0923 0.068 Uiso 1 1 calc R . . N2 N -0.2403(5) 0.19844(19) 1.0404(2) 0.0489(8) Uani 1 1 d . . . N3 N -0.0940(4) 0.2414(2) 1.0015(2) 0.0493(8) Uani 1 1 d . . . H3A H -0.0951 0.2935 1.0004 0.059 Uiso 1 1 calc R . . O1 O 0.0521(4) 0.12431(17) 0.96593(19) 0.0633(8) Uani 1 1 d . . . O2 O 0.0916(7) 0.3969(3) 1.2027(3) 0.1348(18) Uani 1 1 d . . . O3 O 0.3413(8) 0.4429(3) 1.1214(4) 0.160(2) Uani 1 1 d . . . O4 O 0.0771(9) 0.5210(3) 1.1439(3) 0.154(2) Uani 1 1 d . . . O5 O 0.2798(8) 0.4991(4) 1.2537(3) 0.157(2) Uani 1 1 d . . . O6 O -0.2532(5) 0.02399(19) 1.0300(2) 0.0868(11) Uani 1 1 d . . . H61 H -0.1595 0.0544 1.0137 0.13 Uiso 1 1 d R . . H62 H -0.2022 -0.0167 1.054 0.13 Uiso 1 1 d R . . O7 O -0.1809(5) 0.40850(19) 1.0266(2) 0.0800(9) Uani 1 1 d . . . H71 H -0.1454 0.4301 1.0726 0.12 Uiso 1 1 d R . . H72 H -0.1783 0.4353 0.9803 0.12 Uiso 1 1 d R . . Cl1 Cl 0.20073(18) 0.46403(7) 1.18157(8) 0.0676(3) Uani 1 1 d . . . Br1 Br 0.71160(6) 0.17798(3) 0.78876(3) 0.0674(2) 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 C1 0.073(3) 0.075(3) 0.083(3) 0.017(3) 0.011(3) -0.010(3) C2 0.062(3) 0.125(5) 0.072(3) 0.017(3) 0.018(3) -0.017(3) C3 0.055(3) 0.122(5) 0.061(3) -0.010(3) 0.016(2) 0.009(3) C4 0.058(3) 0.078(3) 0.052(2) -0.006(2) 0.002(2) 0.017(2) C5 0.048(2) 0.060(3) 0.039(2) 0.0009(18) -0.0019(16) 0.007(2) C6 0.054(2) 0.050(2) 0.048(2) 0.0017(19) 0.0003(19) 0.005(2) C7 0.045(2) 0.052(3) 0.049(2) 0.0034(18) 0.0001(18) 0.0025(19) C8 0.044(2) 0.053(2) 0.045(2) 0.0059(18) -0.0010(17) -0.0016(19) C9 0.049(2) 0.054(2) 0.046(2) 0.0020(18) -0.0014(18) -0.0003(19) C10 0.046(2) 0.063(3) 0.048(2) 0.001(2) -0.0013(18) -0.002(2) C11 0.054(2) 0.068(3) 0.066(3) 0.008(2) 0.005(2) -0.012(2) C12 0.063(3) 0.051(3) 0.086(3) -0.004(2) 0.011(2) -0.010(2) C13 0.058(3) 0.054(3) 0.069(3) -0.003(2) 0.007(2) 0.000(2) N1 0.0494(19) 0.062(2) 0.060(2) 0.0067(18) 0.0114(16) 0.0054(18) N2 0.0459(18) 0.051(2) 0.0500(18) 0.0035(15) 0.0045(15) 0.0007(16) N3 0.0478(18) 0.0451(18) 0.0552(19) 0.0036(15) 0.0055(15) -0.0013(16) O1 0.0639(18) 0.0446(17) 0.081(2) 0.0057(15) 0.0210(15) 0.0045(15) O2 0.130(4) 0.093(3) 0.182(5) 0.015(3) 0.058(3) -0.037(3) O3 0.157(4) 0.147(4) 0.176(5) -0.048(4) 0.105(4) -0.047(4) O4 0.208(5) 0.128(4) 0.126(4) 0.024(3) -0.029(4) 0.071(4) O5 0.163(5) 0.190(5) 0.118(4) -0.052(4) -0.037(3) -0.021(4) O6 0.075(2) 0.0552(19) 0.130(3) 0.0042(19) 0.038(2) 0.0087(17) O7 0.086(2) 0.065(2) 0.088(2) -0.0028(18) -0.0010(18) 0.0014(19) Cl1 0.0776(7) 0.0535(6) 0.0716(7) 0.0006(6) 0.0072(6) -0.0001(6) Br1 0.0581(3) 0.0789(4) 0.0653(3) 0.0012(2) 0.0157(2) 0.0022(3) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 C1 N1 1.331(6) . ? C1 C2 1.370(7) . ? C2 C3 1.355(8) . ? C3 C4 1.363(7) . ? C4 C5 1.372(6) . ? C5 N1 1.342(5) . ? C5 C6 1.454(5) . ? C6 N2 1.264(5) . ? C7 O1 1.228(5) . ? C7 N3 1.350(5) . ? C7 C8 1.497(5) . ? C8 C13 1.380(6) . ? C8 C9 1.390(5) . ? C9 C10 1.375(5) . ? C10 C11 1.384(6) . ? C10 Br1 1.891(4) . ? C11 C12 1.374(6) . ? C12 C13 1.384(6) . ? N2 N3 1.368(4) . ? O2 Cl1 1.377(4) . ? O3 Cl1 1.386(5) . ? O4 Cl1 1.393(5) . ? O5 Cl1 1.370(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 N1 C1 C2 119.8(5) . . ? C3 C2 C1 119.3(5) . . ? C2 C3 C4 119.8(5) . . ? C3 C4 C5 120.5(5) . . ? N1 C5 C4 118.0(4) . . ? N1 C5 C6 119.2(3) . . ? C4 C5 C6 122.7(4) . . ? N2 C6 C5 117.9(4) . . ? O1 C7 N3 121.3(4) . . ? O1 C7 C8 121.1(4) . . ? N3 C7 C8 117.6(4) . . ? C13 C8 C9 119.2(4) . . ? C13 C8 C7 123.8(4) . . ? C9 C8 C7 116.9(4) . . ? C10 C9 C8 119.8(4) . . ? C9 C10 C11 120.9(4) . . ? C9 C10 Br1 120.0(3) . . ? C11 C10 Br1 119.0(3) . . ? C12 C11 C10 119.2(4) . . ? C11 C12 C13 120.3(4) . . ? C8 C13 C12 120.5(4) . . ? C1 N1 C5 122.6(4) . . ? C6 N2 N3 118.3(3) . . ? C7 N3 N2 117.0(3) . . ? O5 Cl1 O2 111.1(4) . . ? O5 Cl1 O3 112.5(4) . . ? O2 Cl1 O3 109.6(3) . . ? O5 Cl1 O4 107.2(4) . . ? O2 Cl1 O4 108.4(4) . . ? O3 Cl1 O4 108.0(4) . . ? #===END # H2PC4BBH.ClO4.H2O # CIF produced by WinGX routine CIF_UPDATE # Created on 2007-03-16 at 15:20:33 # Using CIFtbx version 2.6.2 16 Jun 1998 # Dictionary name : cif_core.dic # Dictionary vers : 2.3 # Request file : c:\wingx\files\archive.dat # CIF files read : ac29312 dreduc psi_scan struct data_ac29312 _database_code_depnum_ccdc_archive 'CCDC 640844' _audit_creation_date 2007-03-16T15:20:33-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.3 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C13 H11 Br1 N3 O, Cl O4, H2O' _chemical_formula_sum 'C13 H13 Br Cl N3 O6' _chemical_formula_weight 422.62 _chemical_compound_source 'synthesis as described' _chemical_absolute_configuration ad #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P c 21 n' _symmetry_space_group_name_Hall 'P -2n -2ac' _symmetry_Int_Tables_number 33 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' '-x+1/2, y, z+1/2' 'x+1/2, y+1/2, -z+1/2' _cell_length_a 10.4340(10) _cell_length_b 10.7200(6) _cell_length_c 14.691(2) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 1643.2(3) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 9.792 _cell_measurement_theta_max 15.606 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.1 _exptl_crystal_size_min 0.07 _exptl_crystal_density_diffrn 1.708 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 848 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 2.699 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_process_details ; North A.C.T., Phillips D.C. & Mathews F.S. (1968) Acta. Cryst. A24, 351 Number of psi-scan sets used was 3 Theta correction was applied. Averaged transmission function was used. No Fourier smoothing was applied. ; _exptl_absorpt_correction_T_min 0.7322 _exptl_absorpt_correction_T_max 0.8277 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_source 'Enraf Nonius FR590' _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_detector 'scintillation LiI' _diffrn_detector_dtime 1.195 _diffrn_orient_matrix_type ; x-axis points to radiation source the matrix is specified in reciprocal space ; _diffrn_orient_matrix_ub_11 -0.027866 _diffrn_orient_matrix_ub_12 -0.004443 _diffrn_orient_matrix_ub_13 0.065017 _diffrn_orient_matrix_ub_21 -0.091615 _diffrn_orient_matrix_ub_22 -0.002637 _diffrn_orient_matrix_ub_23 -0.019901 _diffrn_orient_matrix_ub_31 0.003972 _diffrn_orient_matrix_ub_32 -0.09317 _diffrn_orient_matrix_ub_33 -0.002557 _diffrn_measurement_device '\k-geometry diffractometer' _diffrn_measurement_device_type 'Enraf Nonius CAD4' _diffrn_measurement_method 'non-profiled omega/2theta scans' _diffrn_standards_number 3 _diffrn_standards_interval_time 120 _diffrn_standards_decay_% -7 loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l -4 0 5 -4 0 -5 -1 -5 -2 _diffrn_reflns_av_R_equivalents 0.0366 _diffrn_reflns_av_unetI/netI 0.0968 _diffrn_reflns_number 2210 _diffrn_reflns_limit_h_min -1 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -1 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -2 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.39 _diffrn_reflns_theta_max 24.97 _diffrn_reflns_theta_full 24.97 _diffrn_measured_fraction_theta_full 1 _diffrn_measured_fraction_theta_max 1 _reflns_number_total 1699 _reflns_number_gt 844 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'CAD4 Express (Enraf Nonius, 1994)' _computing_cell_refinement 'CAD4 Express (Enraf Nonius, 1994)' _computing_data_reduction 'XCAD4 (Harms & Wocadlo, 1995)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.0299P)^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_number_reflns 1699 _refine_ls_number_parameters 217 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.1363 _refine_ls_R_factor_gt 0.0386 _refine_ls_wR_factor_ref 0.0833 _refine_ls_wR_factor_gt 0.0658 _refine_ls_goodness_of_fit_ref 1.01 _refine_ls_restrained_S_all 1.01 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.011(16) _refine_diff_density_max 0.282 _refine_diff_density_min -0.358 _refine_diff_density_rms 0.067 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 '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 0.006 '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' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 C1 C 1.4643(11) -0.3107(11) 0.3253(9) 0.063(3) Uani 1 1 d . . . H1 H 1.4708 -0.3057 0.3883 0.076 Uiso 1 1 calc R . . C2 C 1.5670(10) -0.3534(11) 0.2744(8) 0.071(3) Uani 1 1 d . . . H2 H 1.6414 -0.3813 0.3027 0.085 Uiso 1 1 calc R . . C3 C 1.5566(9) -0.3539(10) 0.1808(8) 0.069(3) Uani 1 1 d . . . H3 H 1.625 -0.3801 0.1449 0.082 Uiso 1 1 calc R . . C4 C 1.4450(9) -0.3156(10) 0.1413(8) 0.052(3) Uani 1 1 d . . . H4 H 1.4378 -0.3166 0.0782 0.062 Uiso 1 1 calc R . . C5 C 1.3441(9) -0.2761(9) 0.1919(7) 0.043(3) Uani 1 1 d . . . C6 C 1.2214(8) -0.2381(8) 0.1561(6) 0.049(3) Uani 1 1 d . . . H6 H 1.2081 -0.2333 0.0937 0.059 Uiso 1 1 calc R . . C7 C 0.9192(10) -0.1452(10) 0.2323(8) 0.049(3) Uani 1 1 d . . . C8 C 0.7969(9) -0.1055(10) 0.1878(7) 0.048(3) Uani 1 1 d . . . C9 C 0.7037(9) -0.0545(9) 0.2454(6) 0.055(3) Uani 1 1 d . . . H9 H 0.7191 -0.049 0.3076 0.066 Uiso 1 1 calc R . . C10 C 0.5892(8) -0.0123(8) 0.2100(6) 0.052(3) Uani 1 1 d . . . H10 H 0.5271 0.0214 0.2481 0.062 Uiso 1 1 calc R . . C11 C 0.5680(8) -0.0203(8) 0.1189(7) 0.051(3) Uani 1 1 d . . . C12 C 0.6590(9) -0.0708(10) 0.0597(7) 0.060(3) Uani 1 1 d . . . H12 H 0.6429 -0.0765 -0.0025 0.072 Uiso 1 1 calc R . . C13 C 0.7714(8) -0.1113(9) 0.0952(7) 0.055(3) Uani 1 1 d . . . H13 H 0.8333 -0.144 0.0564 0.066 Uiso 1 1 calc R . . N1 N 1.3559(8) -0.2767(8) 0.2836(6) 0.055(3) Uani 1 1 d . . . H1A H 1.2914 -0.2545 0.3162 0.066 Uiso 1 1 calc R . . N2 N 1.1326(7) -0.2115(8) 0.2109(5) 0.046(2) Uani 1 1 d . . . N3 N 1.0187(7) -0.1735(7) 0.1745(6) 0.053(2) Uani 1 1 d . . . H3A H 1.0094 -0.1674 0.1165 0.063 Uiso 1 1 calc R . . O1 O 0.9316(7) -0.1517(8) 0.3162(5) 0.069(3) Uani 1 1 d . . . O2 O 1.1673(6) -0.2191(7) 0.4129(4) 0.072(2) Uani 1 1 d . . . H21 H 1.1947 -0.1602 0.4265 0.109 Uiso 1 1 d R . . H22 H 1.109 -0.2118 0.3809 0.109 Uiso 1 1 d R . . O3 O 1.0463(5) -0.4354(11) 0.0643(4) 0.102(4) Uani 1 1 d . . . O4 O 0.9192(9) -0.5910(9) 0.0144(7) 0.118(4) Uani 1 1 d . . . O5 O 0.8648(8) -0.3917(10) -0.0094(6) 0.134(4) Uani 1 1 d . . . O6 O 0.8494(5) -0.4760(10) 0.1342(4) 0.078(2) Uani 1 1 d . . . Cl1 Cl 0.9209(2) -0.4722(4) 0.05141(14) 0.0537(7) Uani 1 1 d . . . Br1 Br 0.40918(8) 0.03587(11) 0.07253(6) 0.0668(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 C1 0.065(7) 0.055(8) 0.071(8) 0.003(7) -0.008(8) 0.007(7) C2 0.062(8) 0.047(7) 0.103(9) 0.007(8) -0.021(7) 0.006(7) C3 0.064(8) 0.038(7) 0.104(9) -0.003(8) 0.009(7) 0.003(6) C4 0.047(6) 0.039(6) 0.070(7) 0.003(6) 0.010(6) 0.014(6) C5 0.045(6) 0.034(7) 0.050(7) 0.001(6) 0.011(6) -0.003(6) C6 0.046(6) 0.049(7) 0.051(7) 0.012(6) -0.001(5) 0.007(6) C7 0.048(6) 0.039(7) 0.061(8) -0.015(6) 0.013(8) -0.016(7) C8 0.041(6) 0.049(7) 0.055(8) 0.001(6) -0.005(6) -0.011(5) C9 0.061(6) 0.056(7) 0.047(6) -0.008(6) 0.007(6) -0.006(6) C10 0.042(5) 0.059(8) 0.053(6) -0.008(5) 0.014(5) 0.002(6) C11 0.041(6) 0.049(6) 0.064(6) 0.010(5) 0.000(5) -0.013(5) C12 0.055(6) 0.072(8) 0.055(6) 0.014(7) 0.006(6) 0.010(6) C13 0.041(6) 0.070(7) 0.053(8) -0.002(6) 0.012(5) 0.010(6) N1 0.045(6) 0.066(7) 0.053(7) 0.005(6) 0.001(6) 0.014(6) N2 0.037(4) 0.048(5) 0.051(5) 0.003(5) 0.000(4) 0.000(4) N3 0.051(5) 0.058(6) 0.049(6) 0.014(5) 0.002(5) 0.007(5) O1 0.061(5) 0.092(7) 0.054(5) -0.006(5) -0.002(4) 0.001(5) O2 0.074(4) 0.084(5) 0.059(4) -0.011(5) -0.004(4) -0.015(4) O3 0.058(4) 0.162(11) 0.087(4) -0.044(7) 0.005(4) -0.044(7) O4 0.165(9) 0.076(6) 0.112(7) -0.041(6) 0.063(7) -0.034(7) O5 0.109(7) 0.176(11) 0.116(7) 0.087(7) -0.019(6) 0.022(6) O6 0.061(4) 0.116(6) 0.058(3) -0.007(7) 0.023(3) 0.010(7) Cl1 0.0458(11) 0.0673(18) 0.0480(12) -0.002(2) -0.0033(11) -0.001(3) Br1 0.0491(5) 0.0736(6) 0.0778(6) 0.0026(12) -0.0007(6) 0.0026(10) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 C1 N1 1.337(12) . ? C1 C2 1.384(13) . ? C2 C3 1.380(13) . ? C3 C4 1.364(12) . ? C4 C5 1.357(12) . ? C5 N1 1.352(11) . ? C5 C6 1.443(12) . ? C6 N2 1.259(9) . ? C7 O1 1.242(12) . ? C7 N3 1.376(11) . ? C7 C8 1.495(13) . ? C8 C13 1.388(11) . ? C8 C9 1.400(12) . ? C9 C10 1.379(11) . ? C10 C11 1.360(11) . ? C11 C12 1.397(11) . ? C11 Br1 1.890(9) . ? C12 C13 1.355(11) . ? N2 N3 1.365(8) . ? O3 Cl1 1.379(6) . ? O4 Cl1 1.385(10) . ? O5 Cl1 1.374(8) . ? O6 Cl1 1.428(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 N1 C1 C2 119.8(11) . . ? C3 C2 C1 118.6(10) . . ? C4 C3 C2 119.3(11) . . ? C5 C4 C3 121.5(11) . . ? N1 C5 C4 118.3(10) . . ? N1 C5 C6 116.4(9) . . ? C4 C5 C6 125.2(10) . . ? N2 C6 C5 119.0(9) . . ? O1 C7 N3 121.5(11) . . ? O1 C7 C8 122.6(11) . . ? N3 C7 C8 115.9(10) . . ? C13 C8 C9 118.5(9) . . ? C13 C8 C7 125.4(10) . . ? C9 C8 C7 116.1(10) . . ? C10 C9 C8 120.1(8) . . ? C11 C10 C9 119.4(8) . . ? C10 C11 C12 121.8(9) . . ? C10 C11 Br1 118.5(8) . . ? C12 C11 Br1 119.7(7) . . ? C13 C12 C11 118.2(9) . . ? C12 C13 C8 121.9(9) . . ? C1 N1 C5 122.3(10) . . ? C6 N2 N3 117.3(7) . . ? N2 N3 C7 118.8(8) . . ? O5 Cl1 O3 108.3(7) . . ? O5 Cl1 O4 108.5(6) . . ? O3 Cl1 O4 109.2(6) . . ? O5 Cl1 O6 110.4(6) . . ? O3 Cl1 O6 112.8(4) . . ? O4 Cl1 O6 107.6(6) . . ? #===END # [Fe(PC2BBH)2].0.5EtOAc # CIF produced by WinGX routine CIF_UPDATE # Created on 2007-03-16 at 14:48:37 # Using CIFtbx version 2.6.2 16 Jun 1998 # Dictionary name : cif_core.dic # Dictionary vers : 2.3 # Request file : c:\wingx\files\archive.dat # CIF files read : 2021ac31 dreduc psi_scan struct1 data_2021ac31 _database_code_depnum_ccdc_archive 'CCDC 640845' _audit_creation_date 2007-03-16T14:48:37-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.3 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C26 H48 Br4 Fe2 N12 O2,0.5(C4 H8 O2)' _chemical_formula_sum 'C28 H22 Br2 Fe N6 O3' _chemical_formula_weight 706.19 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _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 13.833(3) _cell_length_b 14.191(3) _cell_length_c 16.863(2) _cell_angle_alpha 69.80(1) _cell_angle_beta 89.23(1) _cell_angle_gamma 64.05(2) _cell_volume 2756.0(9) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 10.084 _cell_measurement_theta_max 14.164 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour blue-green _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.1 _exptl_crystal_density_diffrn 1.702 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1408 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 3.489 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_process_details ; North A.C.T., Phillips D.C. & Mathews F.S. (1968) Acta. Cryst. A24, 351 Number of psi-scan sets used was 3 Theta correction was applied. Averaged transmission function was used. No Fourier smoothing was applied. ; _exptl_absorpt_correction_T_min 0.6052 _exptl_absorpt_correction_T_max 0.7051 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_source 'Enraf Nonius FR590' _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_detector 'scintillation LiI' _diffrn_detector_dtime 1.195 _diffrn_orient_matrix_type ; x-axis points to radiation source the matrix is specified in reciprocal space ; _diffrn_orient_matrix_ub_11 0.068766 _diffrn_orient_matrix_ub_12 -0.052568 _diffrn_orient_matrix_ub_13 0.042314 _diffrn_orient_matrix_ub_21 0.007574 _diffrn_orient_matrix_ub_22 0.06631 _diffrn_orient_matrix_ub_23 0.001506 _diffrn_orient_matrix_ub_31 -0.043064 _diffrn_orient_matrix_ub_32 0.001617 _diffrn_orient_matrix_ub_33 0.048058 _diffrn_measurement_device '\k-geometry diffractometer' _diffrn_measurement_device_type 'Enraf Nonius TurboCAD4' _diffrn_measurement_method 'non-profiled omega scans' _diffrn_standards_number 3 _diffrn_standards_interval_time 120 _diffrn_standards_decay_% -1 loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l 6 8 5 -3 4 -2 -4 2 6 _diffrn_reflns_av_R_equivalents 0.0906 _diffrn_reflns_av_unetI/netI 0.1804 _diffrn_reflns_number 10126 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.66 _diffrn_reflns_theta_max 24.97 _diffrn_reflns_theta_full 24.97 _diffrn_measured_fraction_theta_full 1 _diffrn_measured_fraction_theta_max 1 _reflns_number_total 9682 _reflns_number_gt 4460 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'CAD4 Express (Enraf Nonius, 1994)' _computing_cell_refinement 'CAD4 Express (Enraf Nonius, 1994)' _computing_data_reduction 'XCAD4 (Harms & Wocadlo, 1995)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.1368P)^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_number_reflns 9682 _refine_ls_number_parameters 711 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.2005 _refine_ls_R_factor_gt 0.0811 _refine_ls_wR_factor_ref 0.2568 _refine_ls_wR_factor_gt 0.1962 _refine_ls_goodness_of_fit_ref 1.003 _refine_ls_restrained_S_all 1.003 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_diff_density_max 2.409 _refine_diff_density_min -1.288 _refine_diff_density_rms 0.2 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Fe Fe 0.3463 0.8444 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 C1A C 0.3339(11) 0.1536(11) 0.8318(8) 0.029(3) Uani 1 1 d . . . H1A H 0.2846 0.1246 0.8364 0.035 Uiso 1 1 calc R . . C1B C 0.1692(10) 0.4432(11) 0.5776(8) 0.025(3) Uani 1 1 d . . . H1B H 0.1991 0.4879 0.5841 0.03 Uiso 1 1 calc R . . C2A C 0.4424(10) 0.0795(11) 0.8581(10) 0.032(4) Uani 1 1 d . . . H2A H 0.4662 0.0019 0.8815 0.039 Uiso 1 1 calc R . . C2B C 0.1595(11) 0.4380(12) 0.4973(9) 0.031(3) Uani 1 1 d . . . H2B H 0.182 0.4784 0.4516 0.038 Uiso 1 1 calc R . . C3A C 0.5172(12) 0.1235(13) 0.8491(10) 0.043(4) Uani 1 1 d . . . H3A H 0.5915 0.0747 0.8653 0.052 Uiso 1 1 calc R . . C3B C 0.1154(11) 0.3709(11) 0.4873(9) 0.028(3) Uiso 1 1 d . . . H3B H 0.108 0.3648 0.4347 0.034 Uiso 1 1 calc R . . C4A C 0.4797(10) 0.2407(11) 0.8158(8) 0.025(3) Uani 1 1 d . . . H4A H 0.5279 0.2714 0.8085 0.03 Uiso 1 1 calc R . . C4B C 0.0824(11) 0.3130(11) 0.5577(9) 0.029(3) Uani 1 1 d . . . H4B H 0.0525 0.2677 0.5524 0.035 Uiso 1 1 calc R . . C5A C 0.3695(10) 0.3082(11) 0.7943(8) 0.021(3) Uani 1 1 d . . . C5B C 0.0935(10) 0.3221(11) 0.6346(8) 0.023(3) Uani 1 1 d . . . C6A C 0.3188(10) 0.4300(10) 0.7641(7) 0.019(3) Uani 1 1 d . . . H6A H 0.3573 0.4712 0.7577 0.022 Uiso 1 1 calc R . . C6B C 0.0602(10) 0.2688(11) 0.7129(8) 0.025(3) Uiso 1 1 d . . . H6B H 0.0271 0.2231 0.7165 0.03 Uiso 1 1 calc R . . C7A C 0.0494(11) 0.6145(9) 0.6991(8) 0.025(3) Uani 1 1 d . . . C7B C 0.0869(9) 0.2834(10) 0.9071(8) 0.017(3) Uani 1 1 d . . . C8A C -0.0350(12) 0.7328(11) 0.6541(9) 0.030(4) Uani 1 1 d . . . C8B C 0.0786(10) 0.2352(10) 0.9972(8) 0.021(3) Uani 1 1 d . . . C9A C -0.0206(12) 0.8136(12) 0.5847(10) 0.040(4) Uani 1 1 d . . . C9B C 0.1642(10) 0.1892(11) 1.0637(9) 0.029(3) Uani 1 1 d . . . C10A C -0.1076(14) 0.9183(12) 0.5471(10) 0.043(4) Uani 1 1 d . . . H10A H -0.099 0.9711 0.5003 0.051 Uiso 1 1 calc R . . C10B C 0.1565(14) 0.1408(13) 1.1477(9) 0.044(4) Uani 1 1 d . . . H10B H 0.2142 0.1103 1.1916 0.053 Uiso 1 1 calc R . . C11A C -0.2046(14) 0.9499(14) 0.5733(12) 0.056(5) Uani 1 1 d . . . H11A H -0.2605 1.0229 0.5453 0.067 Uiso 1 1 calc R . . C11B C 0.0613(13) 0.1395(12) 1.1637(11) 0.051(5) Uani 1 1 d . . . H11B H 0.0582 0.0999 1.2198 0.061 Uiso 1 1 calc R . . C12A C -0.2221(13) 0.8733(14) 0.6428(12) 0.052(5) Uani 1 1 d . . . H12A H -0.289 0.8944 0.6618 0.062 Uiso 1 1 calc R . . C12B C -0.0299(12) 0.1904(12) 1.1056(9) 0.035(4) Uani 1 1 d . . . H12B H -0.0964 0.1958 1.1211 0.042 Uiso 1 1 calc R . . C13A C -0.1376(12) 0.7658(12) 0.6822(10) 0.039(4) Uani 1 1 d . . . H13A H -0.148 0.7137 0.7283 0.046 Uiso 1 1 calc R . . C13B C -0.0171(11) 0.2337(11) 1.0217(8) 0.026(3) Uani 1 1 d . . . H13B H -0.0761 0.2637 0.979 0.031 Uiso 1 1 calc R . . C14A C 0.1836(11) 0.8066(10) 0.1121(8) 0.024(3) Uani 1 1 d . . . H14A H 0.1433 0.7867 0.1534 0.029 Uiso 1 1 calc R . . C14B C 0.2949(10) 0.5196(10) 0.0273(8) 0.021(3) Uani 1 1 d . . . H14B H 0.3512 0.5327 0.0037 0.026 Uiso 1 1 calc R . . C15A C 0.1426(13) 0.9199(12) 0.0586(9) 0.034(4) Uani 1 1 d . . . H15A H 0.0774 0.9744 0.0646 0.041 Uiso 1 1 calc R . . C15B C 0.2336(11) 0.4936(11) -0.0175(8) 0.027(3) Uani 1 1 d . . . H15B H 0.2465 0.4927 -0.0716 0.032 Uiso 1 1 calc R . . C16A C 0.2005(13) 0.9490(12) -0.0031(9) 0.039(4) Uani 1 1 d . . . H16A H 0.1733 1.0238 -0.0411 0.046 Uiso 1 1 calc R . . C16B C 0.1551(11) 0.4695(11) 0.0175(9) 0.027(3) Uani 1 1 d . . . H16B H 0.1152 0.4501 -0.0121 0.033 Uiso 1 1 calc R . . C17A C 0.2962(12) 0.8702(11) -0.0088(8) 0.031(3) Uani 1 1 d . . . H17A H 0.3359 0.8908 -0.0502 0.037 Uiso 1 1 calc R . . C17B C 0.1333(11) 0.4733(10) 0.0966(8) 0.024(3) Uani 1 1 d . . . H17B H 0.0799 0.4555 0.1214 0.029 Uiso 1 1 calc R . . C18A C 0.3369(11) 0.7573(11) 0.0469(8) 0.025(3) Uani 1 1 d . . . C18B C 0.1942(9) 0.5048(11) 0.1388(8) 0.023(3) Uani 1 1 d . . . C19A C 0.4416(11) 0.6626(10) 0.0506(9) 0.026(3) Uani 1 1 d . . . H19A H 0.49 0.6685 0.0127 0.031 Uiso 1 1 calc R . . C19B C 0.1793(9) 0.5170(10) 0.2192(8) 0.019(3) Uani 1 1 d . . . H19B H 0.1288 0.5026 0.2515 0.022 Uiso 1 1 calc R . . C20A C 0.5450(10) 0.3893(11) 0.1888(8) 0.020(3) Uani 1 1 d . . . C20B C 0.3241(9) 0.5912(9) 0.3282(7) 0.014(3) Uani 1 1 d . . . C21A C 0.6361(10) 0.2714(10) 0.2186(8) 0.020(3) Uani 1 1 d . . . C21B C 0.3397(10) 0.6069(11) 0.4075(8) 0.024(3) Uani 1 1 d . . . C22A C 0.6222(10) 0.1859(11) 0.2110(8) 0.022(3) Uani 1 1 d . . . C22B C 0.3313(11) 0.7084(11) 0.4074(9) 0.031(3) Uani 1 1 d . . . C23A C 0.7109(12) 0.0759(11) 0.2406(9) 0.035(4) Uani 1 1 d . . . H23A H 0.7015 0.0173 0.235 0.042 Uiso 1 1 calc R . . C23B C 0.3578(13) 0.7157(14) 0.4855(10) 0.045(4) Uani 1 1 d . . . H23B H 0.3552 0.7823 0.4855 0.054 Uiso 1 1 calc R . . C24A C 0.8100(13) 0.0530(12) 0.2772(9) 0.039(4) Uani 1 1 d . . . H24A H 0.8674 -0.0201 0.2976 0.047 Uiso 1 1 calc R . . C24B C 0.3867(12) 0.6258(14) 0.5594(9) 0.036(4) Uani 1 1 d . . . H24B H 0.4021 0.6314 0.6106 0.043 Uiso 1 1 calc R . . C25A C 0.8224(12) 0.1446(12) 0.2830(9) 0.035(4) Uani 1 1 d . . . H25A H 0.8888 0.1317 0.3079 0.042 Uiso 1 1 calc R . . C25B C 0.3935(10) 0.5282(13) 0.5604(8) 0.030(3) Uani 1 1 d . . . H25B H 0.4153 0.467 0.6123 0.036 Uiso 1 1 calc R . . C26A C 0.7379(10) 0.2513(11) 0.2523(8) 0.028(3) Uani 1 1 d . . . H26A H 0.748 0.3112 0.254 0.034 Uiso 1 1 calc R . . C26B C 0.3687(11) 0.5157(11) 0.4851(8) 0.029(3) Uani 1 1 d . . . H26B H 0.3717 0.4481 0.4872 0.035 Uiso 1 1 calc R . . C27 C 0.6065(13) 0.7450(13) 0.6185(11) 0.052(5) Uani 1 1 d . . . H27A H 0.6623 0.755 0.6422 0.078 Uiso 1 1 calc R . . H27B H 0.6237 0.7332 0.5663 0.078 Uiso 1 1 calc R . . H27C H 0.602 0.6804 0.6587 0.078 Uiso 1 1 calc R . . C28 C 0.5023(14) 0.8454(14) 0.6009(9) 0.040(4) Uani 1 1 d . . . C29 C 0.4129(13) 1.0417(15) 0.5915(11) 0.055(5) Uani 1 1 d . . . H29A H 0.3872 1.077 0.5302 0.066 Uiso 1 1 calc R . . H29B H 0.3554 1.0303 0.6201 0.066 Uiso 1 1 calc R . . C30 C 0.4399(18) 1.1142(17) 0.6196(13) 0.076(6) Uani 1 1 d . . . H30A H 0.3763 1.1856 0.6068 0.115 Uiso 1 1 calc R . . H30B H 0.4961 1.1261 0.5905 0.115 Uiso 1 1 calc R . . H30C H 0.4652 1.0788 0.6803 0.115 Uiso 1 1 calc R . . Br1A Br 0.10528(14) 0.77913(14) 0.53466(10) 0.0449(5) Uani 1 1 d . . . Br1B Br 0.30331(11) 0.17974(12) 1.03915(10) 0.0357(4) Uani 1 1 d . . . Br2A Br 0.48773(12) 0.20636(12) 0.16582(9) 0.0327(4) Uani 1 1 d . . . Br2B Br 0.28340(16) 0.83764(13) 0.30602(11) 0.0486(5) Uani 1 1 d . . . Fe1 Fe 0.14479(14) 0.38545(14) 0.76158(11) 0.0160(4) Uani 1 1 d . . . Fe2 Fe 0.35050(14) 0.56441(14) 0.17708(11) 0.0157(4) Uani 1 1 d . . . N1A N 0.2954(8) 0.2668(8) 0.7995(6) 0.020(2) Uani 1 1 d . . . N1B N 0.1378(8) 0.3871(8) 0.6466(6) 0.021(2) Uani 1 1 d . . . N2A N 0.2139(8) 0.4754(8) 0.7470(6) 0.016(2) Uani 1 1 d . . . N2B N 0.0803(8) 0.2907(8) 0.7757(6) 0.018(2) Uani 1 1 d . . . N3A N 0.1516(8) 0.5936(8) 0.7131(6) 0.019(2) Uani 1 1 d . . . N3B N 0.0587(8) 0.2415(8) 0.8556(6) 0.019(2) Uani 1 1 d . . . N4A N 0.2778(8) 0.7247(8) 0.1075(6) 0.017(2) Uani 1 1 d . . . N4B N 0.2760(7) 0.5267(7) 0.1038(6) 0.013(2) Uani 1 1 d . . . N5A N 0.4582(8) 0.5709(8) 0.1122(6) 0.019(2) Uani 1 1 d . . . N5B N 0.2449(7) 0.5509(8) 0.2426(6) 0.014(2) Uani 1 1 d . . . N6A N 0.5534(9) 0.4704(9) 0.1260(7) 0.025(3) Uani 1 1 d . . . N6B N 0.2411(8) 0.5669(8) 0.3201(6) 0.018(2) Uani 1 1 d . . . O1A O 0.0162(6) 0.5377(6) 0.7184(5) 0.0175(18) Uani 1 1 d . . . O1B O 0.1224(6) 0.3576(7) 0.8821(5) 0.0189(19) Uani 1 1 d . . . O2A O 0.4626(7) 0.4052(7) 0.2294(5) 0.023(2) Uani 1 1 d . . . O2B O 0.3894(6) 0.5967(7) 0.2740(5) 0.0177(18) Uani 1 1 d . . . O3 O 0.4155(12) 0.8607(11) 0.5716(9) 0.074(4) Uani 1 1 d . . . O4 O 0.5105(10) 0.9323(10) 0.6120(7) 0.054(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 C1A 0.024(8) 0.038(8) 0.034(8) -0.011(7) 0.000(6) -0.022(7) C1B 0.016(7) 0.035(8) 0.022(7) -0.009(6) 0.007(6) -0.013(6) C2A 0.022(8) 0.025(7) 0.056(10) -0.022(7) 0.003(7) -0.011(6) C2B 0.035(8) 0.047(9) 0.023(7) -0.014(7) 0.013(6) -0.028(7) C3A 0.023(8) 0.046(10) 0.039(9) 0.000(8) 0.002(7) -0.010(7) C4A 0.016(7) 0.030(8) 0.034(8) -0.012(6) 0.001(6) -0.015(6) C4B 0.033(8) 0.031(8) 0.035(8) -0.016(7) 0.006(7) -0.021(7) C5A 0.028(8) 0.029(7) 0.019(7) -0.016(6) 0.006(6) -0.019(6) C5B 0.025(7) 0.029(7) 0.023(7) -0.016(6) 0.001(6) -0.016(6) C6A 0.025(7) 0.020(7) 0.011(6) 0.004(5) -0.004(5) -0.018(6) C7A 0.031(8) 0.007(6) 0.030(8) -0.007(5) -0.015(6) -0.003(6) C7B 0.013(6) 0.017(6) 0.023(7) -0.013(5) 0.009(5) -0.004(5) C8A 0.045(9) 0.022(7) 0.028(8) -0.003(6) -0.011(7) -0.024(7) C8B 0.021(7) 0.021(7) 0.022(7) -0.011(6) 0.006(6) -0.008(6) C9A 0.034(9) 0.028(8) 0.055(10) -0.023(8) -0.001(8) -0.008(7) C9B 0.015(7) 0.029(8) 0.030(8) -0.005(6) 0.003(6) -0.003(6) C10A 0.055(11) 0.018(7) 0.047(10) -0.002(7) -0.012(8) -0.017(8) C10B 0.069(12) 0.043(9) 0.014(7) 0.001(7) -0.014(8) -0.029(9) C11A 0.041(11) 0.027(9) 0.078(14) -0.026(9) -0.026(10) 0.008(8) C11B 0.044(10) 0.027(8) 0.059(11) 0.020(8) -0.003(9) -0.025(8) C12A 0.032(9) 0.039(10) 0.074(13) -0.030(10) -0.002(9) -0.001(8) C12B 0.036(9) 0.047(9) 0.029(8) -0.017(7) 0.015(7) -0.023(8) C13A 0.031(9) 0.033(8) 0.033(8) -0.007(7) -0.012(7) -0.003(7) C13B 0.033(8) 0.027(7) 0.023(7) -0.008(6) 0.003(6) -0.019(6) C14A 0.028(8) 0.025(7) 0.016(7) -0.005(6) 0.010(6) -0.013(6) C14B 0.014(6) 0.020(7) 0.026(7) -0.011(6) 0.009(6) -0.004(5) C15A 0.042(9) 0.031(8) 0.027(8) -0.008(7) 0.004(7) -0.017(7) C15B 0.030(8) 0.028(8) 0.024(7) -0.009(6) 0.002(6) -0.015(7) C16A 0.046(10) 0.028(8) 0.025(8) -0.003(6) -0.020(7) -0.008(8) C16B 0.025(8) 0.029(8) 0.033(8) -0.020(6) -0.002(6) -0.011(6) C17A 0.056(10) 0.026(8) 0.021(7) -0.003(6) 0.017(7) -0.032(8) C17B 0.026(7) 0.021(7) 0.032(8) -0.011(6) 0.001(6) -0.017(6) C18A 0.034(8) 0.021(7) 0.030(8) -0.015(6) 0.009(6) -0.016(6) C18B 0.007(6) 0.026(7) 0.032(8) -0.013(6) -0.002(6) -0.002(5) C19A 0.030(8) 0.027(7) 0.036(8) -0.014(6) 0.014(6) -0.024(6) C19B 0.005(6) 0.019(6) 0.024(7) 0.002(5) 0.005(5) -0.007(5) C20A 0.018(7) 0.031(7) 0.018(7) -0.016(6) 0.008(5) -0.012(6) C20B 0.011(6) 0.011(6) 0.014(6) -0.003(5) 0.008(5) -0.001(5) C21A 0.027(7) 0.028(7) 0.016(6) -0.013(6) 0.013(6) -0.020(6) C21B 0.016(7) 0.034(8) 0.033(8) -0.020(6) 0.008(6) -0.016(6) C22A 0.025(7) 0.028(7) 0.027(7) -0.015(6) 0.006(6) -0.022(6) C22B 0.031(8) 0.032(8) 0.026(8) -0.007(6) -0.002(6) -0.013(7) C23A 0.042(9) 0.014(7) 0.041(9) -0.013(6) -0.007(7) -0.003(6) C23B 0.057(11) 0.057(11) 0.049(10) -0.038(9) 0.009(9) -0.037(9) C24A 0.050(10) 0.023(8) 0.033(8) -0.012(7) 0.003(8) -0.007(7) C24B 0.038(9) 0.060(10) 0.021(8) -0.027(8) 0.007(7) -0.025(8) C25A 0.031(8) 0.040(9) 0.030(8) -0.012(7) 0.000(7) -0.014(7) C25B 0.019(7) 0.051(9) 0.014(7) -0.012(6) 0.006(6) -0.012(7) C26A 0.019(7) 0.036(8) 0.032(8) -0.016(7) 0.000(6) -0.011(6) C26B 0.031(8) 0.029(8) 0.023(7) -0.003(6) -0.002(6) -0.015(6) C27 0.052(11) 0.040(10) 0.054(11) -0.007(8) 0.023(9) -0.021(9) C28 0.053(11) 0.053(10) 0.021(8) -0.010(7) 0.013(8) -0.033(9) C29 0.035(10) 0.070(13) 0.047(11) -0.017(10) 0.014(8) -0.016(9) C30 0.111(19) 0.064(13) 0.069(14) -0.028(11) 0.019(13) -0.050(13) Br1A 0.0554(11) 0.0450(9) 0.0395(9) -0.0045(7) 0.0038(8) -0.0360(8) Br1B 0.0240(8) 0.0361(8) 0.0404(9) -0.0103(7) -0.0067(7) -0.0112(7) Br2A 0.0381(9) 0.0349(8) 0.0374(8) -0.0170(7) 0.0015(7) -0.0246(7) Br2B 0.0759(13) 0.0329(9) 0.0417(10) -0.0176(7) 0.0107(9) -0.0265(9) Fe1 0.0157(9) 0.0188(9) 0.0178(9) -0.0072(7) 0.0034(7) -0.0115(8) Fe2 0.0168(9) 0.0196(9) 0.0161(9) -0.0076(7) 0.0054(7) -0.0122(8) N1A 0.027(6) 0.023(6) 0.023(6) -0.013(5) 0.010(5) -0.020(5) N1B 0.021(6) 0.024(6) 0.019(6) -0.004(5) 0.008(5) -0.016(5) N2A 0.013(5) 0.018(5) 0.019(5) -0.009(4) -0.002(4) -0.006(4) N2B 0.024(6) 0.023(6) 0.013(5) -0.002(4) 0.000(4) -0.020(5) N3A 0.015(6) 0.016(5) 0.016(5) 0.001(4) -0.004(4) -0.005(4) N3B 0.012(5) 0.019(5) 0.013(5) 0.003(4) 0.001(4) -0.003(4) N4A 0.016(5) 0.019(5) 0.018(5) -0.006(4) 0.005(4) -0.010(5) N4B 0.007(5) 0.013(5) 0.018(5) -0.003(4) 0.004(4) -0.007(4) N5A 0.027(6) 0.013(5) 0.019(6) -0.006(4) 0.005(5) -0.010(5) N5B 0.009(5) 0.020(5) 0.013(5) -0.004(4) 0.006(4) -0.008(4) N6A 0.031(6) 0.027(6) 0.027(6) -0.008(5) 0.011(5) -0.024(5) N6B 0.020(6) 0.026(6) 0.013(5) -0.007(4) -0.001(4) -0.015(5) O1A 0.017(4) 0.019(4) 0.019(4) -0.005(4) 0.005(4) -0.013(4) O1B 0.018(5) 0.020(4) 0.020(5) -0.007(4) 0.003(4) -0.011(4) O2A 0.024(5) 0.026(5) 0.022(5) -0.012(4) 0.010(4) -0.014(4) O2B 0.019(5) 0.027(5) 0.016(4) -0.011(4) 0.009(4) -0.016(4) O3 0.094(11) 0.063(9) 0.076(10) -0.023(7) -0.003(8) -0.047(8) O4 0.059(8) 0.068(8) 0.058(8) -0.030(7) 0.014(6) -0.043(7) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 C1A N1A 1.348(16) . ? C1A C2A 1.367(18) . ? C1B N1B 1.351(15) . ? C1B C2B 1.392(18) . ? C2A C3A 1.41(2) . ? C2B C3B 1.391(18) . ? C3A C4A 1.399(19) . ? C3B C4B 1.390(19) . ? C4A C5A 1.368(17) . ? C4B C5B 1.364(17) . ? C5A N1A 1.375(15) . ? C5A C6A 1.442(17) . ? C5B N1B 1.376(15) . ? C5B C6B 1.459(18) . ? C6A N2A 1.291(15) . ? C6B N2B 1.267(15) . ? C7A O1A 1.301(14) . ? C7A N3A 1.317(16) . ? C7A C8A 1.479(17) . ? C7B O1B 1.291(14) . ? C7B N3B 1.351(15) . ? C7B C8B 1.463(17) . ? C8A C9A 1.41(2) . ? C8A C13A 1.42(2) . ? C8B C13B 1.389(18) . ? C8B C9B 1.391(17) . ? C9A C10A 1.37(2) . ? C9A Br1A 1.867(17) . ? C9B C10B 1.371(19) . ? C9B Br1B 1.920(13) . ? C10A C11A 1.34(2) . ? C10B C11B 1.35(2) . ? C11A C12A 1.40(3) . ? C11B C12B 1.35(2) . ? C12A C13A 1.38(2) . ? C12B C13B 1.378(18) . ? C14A N4A 1.337(16) . ? C14A C15A 1.391(18) . ? C14B N4B 1.341(15) . ? C14B C15B 1.383(17) . ? C15A C16A 1.36(2) . ? C15B C16B 1.346(19) . ? C16A C17A 1.34(2) . ? C16B C17B 1.378(18) . ? C17A C18A 1.397(17) . ? C17B C18B 1.408(16) . ? C18A N4A 1.382(16) . ? C18A C19A 1.466(18) . ? C18B N4B 1.375(15) . ? C18B C19B 1.426(18) . ? C19A N5A 1.279(15) . ? C19B N5B 1.316(15) . ? C20A O2A 1.296(14) . ? C20A N6A 1.316(16) . ? C20A C21A 1.494(17) . ? C20B O2B 1.283(14) . ? C20B N6B 1.357(15) . ? C20B C21B 1.462(17) . ? C21A C22A 1.355(16) . ? C21A C26A 1.394(17) . ? C21B C26B 1.392(18) . ? C21B C22B 1.393(18) . ? C22A C23A 1.413(18) . ? C22A Br2A 1.880(12) . ? C22B C23B 1.422(19) . ? C22B Br2B 1.878(13) . ? C23A C24A 1.36(2) . ? C23B C24B 1.35(2) . ? C24A C25A 1.42(2) . ? C24B C25B 1.34(2) . ? C25A C26A 1.361(18) . ? C25B C26B 1.407(18) . ? C27 C28 1.46(2) . ? C28 O3 1.203(18) . ? C28 O4 1.361(19) . ? C29 C30 1.45(2) . ? C29 O4 1.469(19) . ? Fe1 N2A 1.857(10) . ? Fe1 N2B 1.866(9) . ? Fe1 N1B 1.935(10) . ? Fe1 N1A 1.951(10) . ? Fe1 O1B 1.979(8) . ? Fe1 O1A 1.987(8) . ? Fe2 N5A 1.853(11) . ? Fe2 N5B 1.857(9) . ? Fe2 N4A 1.936(10) . ? Fe2 N4B 1.962(9) . ? Fe2 O2A 1.970(8) . ? Fe2 O2B 1.982(8) . ? N2A N3A 1.403(13) . ? N2B N3B 1.384(13) . ? N5A N6A 1.400(14) . ? N5B N6B 1.398(13) . ? 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 N1A C1A C2A 122.9(12) . . ? N1B C1B C2B 123.9(13) . . ? C1A C2A C3A 118.5(13) . . ? C3B C2B C1B 118.3(13) . . ? C4A C3A C2A 120.0(13) . . ? C4B C3B C2B 118.3(13) . . ? C5A C4A C3A 117.4(12) . . ? C5B C4B C3B 120.5(12) . . ? C4A C5A N1A 123.4(12) . . ? C4A C5A C6A 123.6(11) . . ? N1A C5A C6A 113.0(11) . . ? C4B C5B N1B 122.3(12) . . ? C4B C5B C6B 126.5(12) . . ? N1B C5B C6B 111.2(10) . . ? N2A C6A C5A 112.4(11) . . ? N2B C6B C5B 113.7(12) . . ? O1A C7A N3A 124.9(10) . . ? O1A C7A C8A 116.1(11) . . ? N3A C7A C8A 118.9(11) . . ? O1B C7B N3B 124.6(11) . . ? O1B C7B C8B 120.4(11) . . ? N3B C7B C8B 115.0(11) . . ? C9A C8A C13A 118.3(13) . . ? C9A C8A C7A 124.4(14) . . ? C13A C8A C7A 117.3(13) . . ? C13B C8B C9B 115.7(12) . . ? C13B C8B C7B 121.3(11) . . ? C9B C8B C7B 123.0(12) . . ? C10A C9A C8A 117.8(15) . . ? C10A C9A Br1A 118.7(14) . . ? C8A C9A Br1A 123.1(11) . . ? C10B C9B C8B 122.4(13) . . ? C10B C9B Br1B 117.2(11) . . ? C8B C9B Br1B 120.3(10) . . ? C11A C10A C9A 124.1(17) . . ? C11B C10B C9B 116.8(14) . . ? C10A C11A C12A 120.1(15) . . ? C10B C11B C12B 125.9(15) . . ? C13A C12A C11A 118.2(17) . . ? C11B C12B C13B 114.9(14) . . ? C12A C13A C8A 121.4(16) . . ? C12B C13B C8B 123.8(13) . . ? N4A C14A C15A 123.5(13) . . ? N4B C14B C15B 122.1(12) . . ? C16A C15A C14A 118.4(14) . . ? C16B C15B C14B 119.7(13) . . ? C17A C16A C15A 120.0(14) . . ? C15B C16B C17B 120.7(12) . . ? C16A C17A C18A 120.6(13) . . ? C16B C17B C18B 118.0(13) . . ? N4A C18A C17A 120.6(12) . . ? N4A C18A C19A 112.5(11) . . ? C17A C18A C19A 126.9(13) . . ? N4B C18B C17B 121.0(12) . . ? N4B C18B C19B 113.7(11) . . ? C17B C18B C19B 125.2(12) . . ? N5A C19A C18A 111.8(12) . . ? N5B C19B C18B 112.6(11) . . ? O2A C20A N6A 124.0(11) . . ? O2A C20A C21A 116.5(11) . . ? N6A C20A C21A 119.4(11) . . ? O2B C20B N6B 125.0(11) . . ? O2B C20B C21B 119.9(11) . . ? N6B C20B C21B 115.1(10) . . ? C22A C21A C26A 120.2(12) . . ? C22A C21A C20A 121.4(11) . . ? C26A C21A C20A 118.3(11) . . ? C26B C21B C22B 119.1(12) . . ? C26B C21B C20B 118.8(11) . . ? C22B C21B C20B 122.0(12) . . ? C21A C22A C23A 119.0(12) . . ? C21A C22A Br2A 122.7(10) . . ? C23A C22A Br2A 118.2(9) . . ? C21B C22B C23B 119.8(13) . . ? C21B C22B Br2B 121.4(10) . . ? C23B C22B Br2B 118.8(11) . . ? C24A C23A C22A 121.9(13) . . ? C24B C23B C22B 119.7(14) . . ? C23A C24A C25A 117.6(13) . . ? C25B C24B C23B 121.0(13) . . ? C26A C25A C24A 120.6(13) . . ? C24B C25B C26B 121.9(13) . . ? C25A C26A C21A 120.5(13) . . ? C21B C26B C25B 118.5(13) . . ? O3 C28 O4 119.2(16) . . ? O3 C28 C27 126.9(17) . . ? O4 C28 C27 113.6(15) . . ? C30 C29 O4 109.1(15) . . ? N2A Fe1 N2B 177.7(5) . . ? N2A Fe1 N1B 98.2(4) . . ? N2B Fe1 N1B 81.0(4) . . ? N2A Fe1 N1A 80.9(4) . . ? N2B Fe1 N1A 97.0(4) . . ? N1B Fe1 N1A 94.7(4) . . ? N2A Fe1 O1B 100.7(4) . . ? N2B Fe1 O1B 80.2(4) . . ? N1B Fe1 O1B 161.0(4) . . ? N1A Fe1 O1B 90.4(4) . . ? N2A Fe1 O1A 80.0(4) . . ? N2B Fe1 O1A 102.0(4) . . ? N1B Fe1 O1A 88.2(4) . . ? N1A Fe1 O1A 160.9(4) . . ? O1B Fe1 O1A 92.9(3) . . ? N5A Fe2 N5B 177.3(4) . . ? N5A Fe2 N4A 81.5(4) . . ? N5B Fe2 N4A 100.9(4) . . ? N5A Fe2 N4B 97.4(4) . . ? N5B Fe2 N4B 81.2(4) . . ? N4A Fe2 N4B 93.6(4) . . ? N5A Fe2 O2A 80.5(4) . . ? N5B Fe2 O2A 97.2(4) . . ? N4A Fe2 O2A 161.8(4) . . ? N4B Fe2 O2A 90.9(4) . . ? N5A Fe2 O2B 101.3(4) . . ? N5B Fe2 O2B 80.1(4) . . ? N4A Fe2 O2B 90.2(4) . . ? N4B Fe2 O2B 161.2(4) . . ? O2A Fe2 O2B 91.1(3) . . ? C1A N1A C5A 117.7(11) . . ? C1A N1A Fe1 129.0(9) . . ? C5A N1A Fe1 113.2(8) . . ? C1B N1B C5B 116.6(11) . . ? C1B N1B Fe1 129.2(9) . . ? C5B N1B Fe1 114.2(8) . . ? C6A N2A N3A 120.1(10) . . ? C6A N2A Fe1 120.5(8) . . ? N3A N2A Fe1 119.4(7) . . ? C6B N2B N3B 120.5(10) . . ? C6B N2B Fe1 119.9(9) . . ? N3B N2B Fe1 119.5(7) . . ? C7A N3A N2A 106.4(9) . . ? C7B N3B N2B 105.9(9) . . ? C14A N4A C18A 116.9(10) . . ? C14A N4A Fe2 130.0(9) . . ? C18A N4A Fe2 113.1(8) . . ? C14B N4B C18B 118.3(10) . . ? C14B N4B Fe2 129.0(8) . . ? C18B N4B Fe2 112.7(8) . . ? C19A N5A N6A 120.5(11) . . ? C19A N5A Fe2 120.8(9) . . ? N6A N5A Fe2 118.3(7) . . ? C19B N5B N6B 120.0(10) . . ? C19B N5B Fe2 119.5(8) . . ? N6B N5B Fe2 120.3(7) . . ? C20A N6A N5A 107.3(10) . . ? C20B N6B N5B 104.9(9) . . ? C7A O1A Fe1 109.1(7) . . ? C7B O1B Fe1 109.2(7) . . ? C20A O2A Fe2 109.6(8) . . ? C20B O2B Fe2 109.8(7) . . ? C28 O4 C29 119.8(13) . . ?