#------------------------------------------------------------------------------ #$Date: 2014-04-18 13:07:51 +0300 (Fri, 18 Apr 2014) $ #$Revision: 110325 $ #$URL: file:///home/coder/svn-repositories/cod/cif/4/33/78/4337862.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/ # # All data on this site have been placed in the public domain by the # contributors. # data_4337862 loop_ _publ_author_name 'Cui, Huiling' 'Goddard, Richard' 'P\"orschke, Klaus-Richard' 'Hamacher, Alexandra' 'Kassack, Matthias U.' _publ_section_title ; Bispidine Analogues of Cisplatin, Carboplatin, and Oxaliplatin. Synthesis, Structures, and Cytotoxicity. ; _journal_issue 7 _journal_name_full 'Inorganic chemistry' _journal_page_first 3371 _journal_paper_doi 10.1021/ic402737f _journal_volume 53 _journal_year 2014 _chemical_compound_source dimethylformamide _chemical_formula_moiety 'C7 H14 Cl2 N2 Pt, C3 H7 N O' _chemical_formula_sum 'C10 H21 Cl2 N3 O Pt' _chemical_formula_weight 465.29 _chemical_name_systematic ; N,N'-3,7-diazabicyclo[3.3.1]nonane-dichloro-platinum(ii) dimethylformamide ; _space_group_IT_number 2 _symmetry_cell_setting triclinic _symmetry_Int_Tables_number 2 _symmetry_space_group_name_Hall '-P 1' _symmetry_space_group_name_H-M 'P -1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_block_code CUI-CA-103-01 _audit_creation_date 2012-02-08 _cell_angle_alpha 91.573(2) _cell_angle_beta 94.723(2) _cell_angle_gamma 92.842(2) _cell_formula_units_Z 2 _cell_length_a 6.4029(7) _cell_length_b 6.7311(8) _cell_length_c 16.8847(19) _cell_measurement_reflns_used 26539 _cell_measurement_temperature 100 _cell_measurement_theta_max 36.55 _cell_measurement_theta_min 3.51 _cell_volume 723.98(14) _computing_cell_refinement 'SAINT software (Bruker AXS, 2004)' _computing_data_collection 'APEX2 (Bruker AXS, 2008)' _computing_data_reduction 'SAINT software (Bruker AXS, 2004)' _computing_molecular_graphics 'DIAMOND (Crystal Impact GbR, 2005)' _computing_publication_material ; OLEX2: a complete structure solution, refinement and analysis program. Dolomanov et al., J. Appl. Cryst. (2009). 42, 339-341 ; _computing_structure_refinement 'SHELXL-97 (G. M. Sheldrick, 2008)' _computing_structure_solution 'SHELXS-97 (G. M. Sheldrick, 2008)' _diffrn_ambient_temperature 100 _diffrn_detector_area_resol_mean 66.67 _diffrn_measured_fraction_theta_full 0.993 _diffrn_measured_fraction_theta_max 0.939 _diffrn_measurement_device_type 'Bruker-AXS Smart APEX-II' _diffrn_measurement_method 'CCD \f- and \w-scans' _diffrn_radiation_monochromator 'Incoatec Helios mirrors' _diffrn_radiation_source '0.2 x 2mm^2^ focus rotating anode' _diffrn_radiation_type Mo-K\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0569 _diffrn_reflns_av_sigmaI/netI 0.0457 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_number 26539 _diffrn_reflns_theta_full 27.75 _diffrn_reflns_theta_max 36.55 _diffrn_reflns_theta_min 3.51 _diffrn_standards_decay_% 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 10.049 _exptl_absorpt_correction_T_max 0.97 _exptl_absorpt_correction_T_min 0.53 _exptl_absorpt_correction_type gaussian _exptl_absorpt_process_details 'SADABS (Bruker AXS, 2008)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 2.134 _exptl_crystal_description plate _exptl_crystal_F_000 444 _exptl_crystal_size_max 0.03 _exptl_crystal_size_mid 0.02 _exptl_crystal_size_min 0.02 _refine_diff_density_max 4.731 _refine_diff_density_min -4.394 _refine_diff_density_rms 0.300 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.179 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 156 _refine_ls_number_reflns 6699 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.179 _refine_ls_R_factor_all 0.0386 _refine_ls_R_factor_gt 0.0358 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details ; calc w=1/[\s^2^(Fo^2^)+(0.0168P)^2^+7.1293P] where P=(Fo^2^+2Fc^2^)/3 ; _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0958 _refine_ls_wR_factor_ref 0.0969 _reflns_number_gt 6318 _reflns_number_total 6699 _reflns_threshold_expression >2sigma(I) _iucr_refine_instructions_details ; TITL 6821sadabs in P-1 CELL 0.71073 6.4029 6.7311 16.8847 91.573 94.723 92.842 ZERR 2 0.0007 0.0008 0.0019 0.002 0.002 0.002 LATT 1 SFAC C H N Cl O Pt UNIT 20 42 6 4 2 2 L.S. 10 PLAN 10 BOND FMAP 2.0 ACTA 55.5 SHEL 6 0.05 OMIT 1 2 7 OMIT 3 5 7 OMIT 3 6 15 OMIT 2 3 7 OMIT 2 3 4 OMIT 4 6 7 OMIT 4 6 10 WGHT 0.0168 7.1293 FVAR 0.14631 PT1 6 0.50547 0.98294 0.68721 11.00000 0.01291 0.01132 0.01063 = 0.00076 -0.00014 0.00006 CL1 4 0.66419 1.16640 0.59204 11.00000 0.02221 0.01694 0.01399 = 0.00105 0.00117 -0.00578 CL2 4 0.69188 1.15733 0.79311 11.00000 0.01997 0.01887 0.01387 = -0.00174 -0.00203 -0.00205 O1 5 0.35975 0.75518 0.93134 11.00000 0.02401 0.03100 0.02004 = 0.00447 -0.00105 0.00068 N1 3 0.33140 0.82364 0.59863 11.00000 0.01470 0.01546 0.01274 = 0.00039 0.00002 -0.00146 AFIX 13 H1 2 0.36875 0.87129 0.55161 11.00000 -1.20000 AFIX 0 N2 3 0.35376 0.80978 0.76304 11.00000 0.01641 0.01383 0.01411 = 0.00248 0.00371 0.00036 AFIX 13 H2A 2 0.40290 0.84765 0.81358 11.00000 -1.20000 AFIX 0 N3 3 0.67747 0.74380 1.00241 11.00000 0.02463 0.02250 0.01413 = 0.00182 -0.00065 0.00099 C1 1 0.10156 0.85294 0.60211 11.00000 0.01498 0.02650 0.01712 = 0.00292 -0.00215 -0.00191 AFIX 23 H1C 2 0.02511 0.79702 0.55399 11.00000 -1.20000 H1B 2 0.07837 0.99417 0.60506 11.00000 -1.20000 AFIX 0 C2 1 0.01879 0.75283 0.67450 11.00000 0.01342 0.02872 0.02161 = -0.00007 0.00226 -0.00541 AFIX 13 H2 2 -0.13253 0.77006 0.67318 11.00000 -1.20000 AFIX 0 C3 1 0.12169 0.83963 0.75403 11.00000 0.01718 0.02351 0.01982 = -0.00018 0.00427 0.00081 AFIX 23 H3A 2 0.09873 0.98084 0.75762 11.00000 -1.20000 H3B 2 0.05585 0.77634 0.79722 11.00000 -1.20000 AFIX 0 C4 1 0.39628 0.59331 0.75040 11.00000 0.02664 0.01441 0.01687 = 0.00428 0.00404 0.00092 AFIX 23 H4C 2 0.34454 0.51784 0.79350 11.00000 -1.20000 H4B 2 0.54656 0.57941 0.75155 11.00000 -1.20000 AFIX 0 C5 1 0.29199 0.50802 0.67145 11.00000 0.02834 0.01268 0.02212 = 0.00116 0.00445 -0.00313 AFIX 13 H5 2 0.31798 0.36593 0.66787 11.00000 -1.20000 AFIX 0 C6 1 0.37576 0.60810 0.59921 11.00000 0.02371 0.01234 0.01911 = -0.00147 0.00281 -0.00163 AFIX 23 H6A 2 0.52600 0.59409 0.60028 11.00000 -1.20000 H6B 2 0.31075 0.54224 0.55090 11.00000 -1.20000 AFIX 0 C7 1 0.05380 0.53007 0.66847 11.00000 0.02783 0.02484 0.02338 = -0.00151 0.00483 -0.01330 AFIX 23 H7A 2 -0.01403 0.47271 0.61901 11.00000 -1.20000 H7B 2 -0.00420 0.46234 0.71232 11.00000 -1.20000 AFIX 0 C97 1 0.47025 0.76245 0.99507 11.00000 0.02639 0.01929 0.01586 = 0.00156 0.00294 0.00102 AFIX 43 H97A 2 0.40395 0.78243 1.04140 11.00000 -1.20000 AFIX 0 C98 1 0.78939 0.71135 0.93145 11.00000 0.02622 0.03738 0.02008 = 0.00445 0.00421 0.00646 AFIX 137 H98A 2 0.74355 0.58479 0.90673 11.00000 -1.50000 H98B 2 0.93749 0.71296 0.94626 11.00000 -1.50000 H98C 2 0.76061 0.81499 0.89478 11.00000 -1.50000 AFIX 0 C99 1 0.80090 0.76117 1.07851 11.00000 0.02789 0.03668 0.02145 = 0.00735 -0.00232 0.00168 AFIX 137 H99A 2 0.87709 0.64312 1.08664 11.00000 -1.50000 H99B 2 0.70939 0.77718 1.12024 11.00000 -1.50000 H99C 2 0.89791 0.87471 1.07901 11.00000 -1.50000 AFIX 0 HKLF 4 END ; _[local]_cod_data_source_file ic402737f_si_002.cif _[local]_cod_data_source_block 1b _[local]_cod_cif_authors_sg_H-M P-1 _cod_depositor_comments 'Adding full bibliography for 4337861--4337865.cif.' _cod_database_code 4337862 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' 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 Pt1 Pt 0.50547(2) 0.98294(2) 0.687208(9) 0.01169(4) Uani 1 1 d . Cl1 Cl 0.66419(19) 1.16640(17) 0.59204(6) 0.01795(18) Uani 1 1 d . Cl2 Cl 0.69188(18) 1.15733(17) 0.79311(6) 0.01790(18) Uani 1 1 d . O1 O 0.3598(7) 0.7552(7) 0.9313(2) 0.0251(8) Uani 1 1 d . N1 N 0.3314(6) 0.8236(6) 0.5986(2) 0.0144(6) Uani 1 1 d . H1 H 0.3688 0.8713 0.5516 0.017 Uiso 1 1 calc R N2 N 0.3538(6) 0.8098(6) 0.7630(2) 0.0146(6) Uani 1 1 d . H2A H 0.4029 0.8476 0.8136 0.018 Uiso 1 1 calc R N3 N 0.6775(7) 0.7438(7) 1.0024(2) 0.0205(7) Uani 1 1 d . C1 C 0.1016(7) 0.8529(8) 0.6021(3) 0.0198(8) Uani 1 1 d . H1C H 0.0251 0.7970 0.5540 0.024 Uiso 1 1 calc R H1B H 0.0784 0.9942 0.6051 0.024 Uiso 1 1 calc R C2 C 0.0188(8) 0.7528(8) 0.6745(3) 0.0214(9) Uani 1 1 d . H2 H -0.1325 0.7701 0.6732 0.026 Uiso 1 1 calc R C3 C 0.1217(8) 0.8396(8) 0.7540(3) 0.0200(8) Uani 1 1 d . H3A H 0.0987 0.9808 0.7576 0.024 Uiso 1 1 calc R H3B H 0.0558 0.7763 0.7972 0.024 Uiso 1 1 calc R C4 C 0.3963(8) 0.5933(7) 0.7504(3) 0.0191(8) Uani 1 1 d . H4C H 0.3445 0.5178 0.7935 0.023 Uiso 1 1 calc R H4B H 0.5466 0.5794 0.7516 0.023 Uiso 1 1 calc R C5 C 0.2920(9) 0.5080(7) 0.6715(3) 0.0210(9) Uani 1 1 d . H5 H 0.3180 0.3659 0.6679 0.025 Uiso 1 1 calc R C6 C 0.3758(8) 0.6081(7) 0.5992(3) 0.0185(8) Uani 1 1 d . H6A H 0.5260 0.5941 0.6003 0.022 Uiso 1 1 calc R H6B H 0.3108 0.5422 0.5509 0.022 Uiso 1 1 calc R C7 C 0.0538(9) 0.5301(9) 0.6685(3) 0.0257(10) Uani 1 1 d . H7A H -0.0140 0.4727 0.6190 0.031 Uiso 1 1 calc R H7B H -0.0042 0.4623 0.7123 0.031 Uiso 1 1 calc R C97 C 0.4702(9) 0.7625(8) 0.9951(3) 0.0204(8) Uani 1 1 d . H97A H 0.4039 0.7824 1.0414 0.025 Uiso 1 1 calc R C98 C 0.7894(9) 0.7113(10) 0.9314(3) 0.0275(11) Uani 1 1 d . H98A H 0.7435 0.5848 0.9067 0.041 Uiso 1 1 calc R H98B H 0.9375 0.7130 0.9463 0.041 Uiso 1 1 calc R H98C H 0.7606 0.8150 0.8948 0.041 Uiso 1 1 calc R C99 C 0.8009(10) 0.7612(10) 1.0785(3) 0.0288(11) Uani 1 1 d . H99A H 0.8771 0.6431 1.0866 0.043 Uiso 1 1 calc R H99B H 0.7094 0.7772 1.1202 0.043 Uiso 1 1 calc R H99C H 0.8979 0.8747 1.0790 0.043 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 Pt1 0.01291(7) 0.01132(7) 0.01063(7) 0.00076(4) -0.00014(4) 0.00006(5) Cl1 0.0222(5) 0.0169(4) 0.0140(4) 0.0010(3) 0.0012(3) -0.0058(4) Cl2 0.0200(5) 0.0189(4) 0.0139(4) -0.0017(3) -0.0020(3) -0.0021(4) O1 0.0240(18) 0.031(2) 0.0200(17) 0.0045(14) -0.0011(13) 0.0007(15) N1 0.0147(15) 0.0155(15) 0.0127(14) 0.0004(11) 0.0000(11) -0.0015(12) N2 0.0164(16) 0.0138(15) 0.0141(15) 0.0025(11) 0.0037(12) 0.0004(12) N3 0.025(2) 0.0225(19) 0.0141(16) 0.0018(13) -0.0007(14) 0.0010(15) C1 0.0150(18) 0.026(2) 0.0171(19) 0.0029(16) -0.0022(14) -0.0019(16) C2 0.0134(18) 0.029(2) 0.022(2) -0.0001(17) 0.0023(15) -0.0054(16) C3 0.0172(19) 0.024(2) 0.020(2) -0.0002(16) 0.0043(15) 0.0008(16) C4 0.027(2) 0.0144(17) 0.0169(18) 0.0043(14) 0.0040(16) 0.0009(16) C5 0.028(2) 0.0127(17) 0.022(2) 0.0012(15) 0.0044(17) -0.0031(16) C6 0.024(2) 0.0123(17) 0.0191(19) -0.0015(14) 0.0028(15) -0.0016(15) C7 0.028(3) 0.025(2) 0.023(2) -0.0015(18) 0.0048(18) -0.013(2) C97 0.026(2) 0.019(2) 0.0159(18) 0.0016(15) 0.0029(16) 0.0010(17) C98 0.026(3) 0.037(3) 0.020(2) 0.004(2) 0.0042(18) 0.006(2) C99 0.028(3) 0.037(3) 0.021(2) 0.007(2) -0.0023(19) 0.002(2) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Pt Pt -1.7033 8.3905 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist 0.00 1.00 0.00 0.0100 0.00 -1.00 0.00 0.0100 -2.00 2.00 1.00 0.0100 2.00 -2.00 1.00 0.0100 0.00 0.00 1.00 0.0100 0.00 0.00 -1.00 0.0200 loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_publ_flag N2 Pt1 N1 85.99(16) y N2 Pt1 Cl1 175.38(11) y N1 Pt1 Cl1 89.40(12) y N2 Pt1 Cl2 90.97(12) y N1 Pt1 Cl2 176.87(12) y Cl1 Pt1 Cl2 93.65(4) y C6 N1 C1 111.2(4) y C6 N1 Pt1 112.0(3) y C1 N1 Pt1 111.3(3) y C3 N2 C4 110.7(4) y C3 N2 Pt1 110.5(3) y C4 N2 Pt1 111.2(3) y C97 N3 C99 122.7(5) y C97 N3 C98 119.8(4) y C99 N3 C98 117.5(5) y N1 C1 C2 110.9(4) y C7 C2 C1 108.9(4) y C7 C2 C3 109.6(4) y C1 C2 C3 113.4(4) y N2 C3 C2 111.9(4) y N2 C4 C5 112.0(4) y C4 C5 C6 113.1(4) y C4 C5 C7 109.9(4) y C6 C5 C7 108.7(4) y N1 C6 C5 111.2(4) y C2 C7 C5 107.0(4) y O1 C97 N3 125.0(5) y loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag Pt1 N2 2.029(4) y Pt1 N1 2.037(4) y Pt1 Cl1 2.3224(12) y Pt1 Cl2 2.3226(11) y O1 C97 1.237(6) y N1 C6 1.492(6) y N1 C1 1.500(6) y N2 C3 1.505(6) y N2 C4 1.508(6) y N3 C97 1.335(7) y N3 C99 1.451(7) y N3 C98 1.463(7) y C1 C2 1.531(7) y C2 C7 1.529(8) y C2 C3 1.534(7) y C4 C5 1.525(7) y C5 C6 1.532(7) y C5 C7 1.536(8) y