#------------------------------------------------------------------------------ #$Date: 2016-03-21 08:18:08 +0000 (Mon, 21 Mar 2016) $ #$Revision: 178644 $ #$URL: svn://www.crystallography.net/cod/cif/4/07/55/4075599.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_4075599 loop_ _publ_author_name 'Dorcier, Antoine' 'Ang, Wee Han' 'Bola\~no, Sandra' 'Gonsalvi, Luca' 'Juillerat-Jeannerat, Lucienne' 'Laurenczy, G\`abor' 'Peruzzini, Maurizio' 'Phillips, Andrew D.' 'Zanobini, Fabrizio' 'Dyson, Paul J.' _publ_section_title ; In Vitro Evaluation of Rhodium and Osmium RAPTA Analogues:  The Case for Organometallic Anticancer Drugs Not Based on Ruthenium ; _journal_issue 17 _journal_name_full Organometallics _journal_page_first 4090 _journal_paper_doi 10.1021/om060394o _journal_volume 25 _journal_year 2006 _chemical_absolute_configuration unk _chemical_compound_source 'synthesis as described' _chemical_formula_moiety 'C16 H27 Cl2 N3 P Rh' _chemical_formula_sum 'C16 H27 Cl2 N3 P Rh' _chemical_formula_weight 466.19 _chemical_name_common Cp*RhCl2(PTA) _chemical_name_systematic ; Bischloro-Pentamethylcyclodienyl-1,3,5-Triaza-7-phosphaadamantane- Rhodium(III) ; _space_group_IT_number 19 _symmetry_cell_setting orthorhombic _symmetry_Int_Tables_number 19 _symmetry_space_group_name_Hall 'P 2ac 2ab' _symmetry_space_group_name_H-M 'P 21 21 21' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-97 _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 8.500(3) _cell_length_b 13.382(6) _cell_length_c 16.361(9) _cell_measurement_reflns_used 25 _cell_measurement_temperature 200(2) _cell_measurement_theta_max 27.0 _cell_measurement_theta_min 2.5 _cell_volume 1861.0(15) _computing_cell_refinement 'CAD4 Express (Enraf Nonius, 1994)' _computing_data_collection 'CAD4 Express (Enraf Nonius, 1994)' _computing_data_reduction 'XCAD4 (Harms & Wocadlo, 1995)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material ; WinGX publication routines (Farrugia, 1999) ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _diffrn_ambient_temperature 200(2) _diffrn_detector 'scintillation LiI' _diffrn_detector_dtime 1.195 _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.998 _diffrn_measurement_device '\k-geometry diffractometer' _diffrn_measurement_device_type 'Enraf Nonius CAD4' _diffrn_measurement_method 'non-profiled omega/2theta scans' _diffrn_orient_matrix_type ; x-axis points to radiation source the matrix is specified in reciprocal space ; _diffrn_orient_matrix_UB_11 0.108596 _diffrn_orient_matrix_UB_12 -0.023769 _diffrn_orient_matrix_UB_13 -0.013053 _diffrn_orient_matrix_UB_21 -0.024159 _diffrn_orient_matrix_UB_22 -0.065830 _diffrn_orient_matrix_UB_23 0.025972 _diffrn_orient_matrix_UB_31 -0.038109 _diffrn_orient_matrix_UB_32 -0.026071 _diffrn_orient_matrix_UB_33 -0.053814 _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0256 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_number 2310 _diffrn_reflns_theta_full 26.97 _diffrn_reflns_theta_max 26.97 _diffrn_reflns_theta_min 2.70 _diffrn_source 'Enraf Nonius FR590' _diffrn_standards_decay_% 0 _diffrn_standards_interval_time 83 _diffrn_standards_number 2 _exptl_absorpt_coefficient_mu 1.293 _exptl_absorpt_correction_T_max 0.9382 _exptl_absorpt_correction_T_min 0.8816 _exptl_absorpt_correction_type empirical _exptl_absorpt_process_details ; xAbs2 - Parkin, S., Moezzi, B. & Hope H. (1995) J. Appl. Cryst. 28, 53-56 ; _exptl_crystal_colour red _exptl_crystal_density_diffrn 1.664 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 952 _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.09 _exptl_crystal_size_min 0.05 _refine_diff_density_max 0.306 _refine_diff_density_min -0.349 _refine_diff_density_rms 0.063 _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.01(3) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.047 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 213 _refine_ls_number_reflns 2310 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.047 _refine_ls_R_factor_all 0.0223 _refine_ls_R_factor_gt 0.0190 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0231P)^2^+0.5113P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0472 _refine_ls_wR_factor_ref 0.0480 _reflns_number_gt 2180 _reflns_number_total 2310 _reflns_threshold_expression I>2/s(I) _cod_data_source_file om060394osi20060505_051727.cif _cod_data_source_block adp145 _cod_database_code 4075599 #BEGIN Tags that were not found in dictionaries: _diffrn_standards_decay_corr_max 1.016 _diffrn_standards_decay_corr_min 0.997 #END Tags that were not found in dictionaries loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' 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 C1 C 1.0720(4) 0.5299(2) 0.3471(2) 0.0234(7) Uani 1 1 d . H1A H 1.0098 0.4727 0.3265 0.028 Uiso 1 1 calc R H1B H 1.1659 0.5373 0.3118 0.028 Uiso 1 1 calc R C2 C 0.8114(4) 0.6167(3) 0.42416(19) 0.0239(7) Uani 1 1 d . H2A H 0.7478 0.6770 0.4359 0.029 Uiso 1 1 calc R H2B H 0.7390 0.5633 0.4058 0.029 Uiso 1 1 calc R C3 C 1.0848(4) 0.7286(2) 0.3992(2) 0.0248(7) Uani 1 1 d . H3A H 1.1793 0.7426 0.3657 0.030 Uiso 1 1 calc R H3B H 1.0306 0.7929 0.4095 0.030 Uiso 1 1 calc R C4 C 1.2184(4) 0.5909(3) 0.4651(2) 0.0265(8) Uani 1 1 d . H4A H 1.2626 0.5690 0.5182 0.032 Uiso 1 1 calc R H4B H 1.3076 0.6034 0.4276 0.032 Uiso 1 1 calc R C5 C 0.9869(4) 0.4942(3) 0.4853(2) 0.0294(8) Uani 1 1 d . H5A H 1.0251 0.4688 0.5385 0.035 Uiso 1 1 calc R H5B H 0.9186 0.4421 0.4611 0.035 Uiso 1 1 calc R C6 C 0.9963(4) 0.6642(3) 0.5295(2) 0.0290(8) Uani 1 1 d . H6A H 0.9341 0.7264 0.5347 0.035 Uiso 1 1 calc R H6B H 1.0340 0.6459 0.5848 0.035 Uiso 1 1 calc R C7 C 0.7228(4) 0.5730(2) 0.1849(2) 0.0232(7) Uani 1 1 d . C8 C 0.8197(4) 0.6077(2) 0.11958(18) 0.0191(7) Uani 1 1 d . C9 C 0.7616(4) 0.7051(2) 0.09465(18) 0.0183(6) Uani 1 1 d . C10 C 0.6370(4) 0.7314(2) 0.14732(19) 0.0227(7) Uani 1 1 d . C11 C 0.6156(4) 0.6514(3) 0.20580(19) 0.0254(7) Uani 1 1 d . C12 C 0.7284(5) 0.4692(3) 0.2206(2) 0.0338(8) Uani 1 1 d . H12A H 0.6987 0.4718 0.2785 0.051 Uiso 1 1 calc R H12B H 0.8353 0.4425 0.2156 0.051 Uiso 1 1 calc R H12C H 0.6549 0.4259 0.1910 0.051 Uiso 1 1 calc R C13 C 0.9476(5) 0.5507(3) 0.0781(2) 0.0290(8) Uani 1 1 d . H13A H 0.9937 0.5028 0.1166 0.044 Uiso 1 1 calc R H13B H 1.0290 0.5972 0.0593 0.044 Uiso 1 1 calc R H13C H 0.9040 0.5146 0.0311 0.044 Uiso 1 1 calc R C14 C 0.8233(4) 0.7651(2) 0.02488(19) 0.0260(7) Uani 1 1 d . H14A H 0.7726 0.7433 -0.0259 0.039 Uiso 1 1 calc R H14B H 0.9373 0.7554 0.0205 0.039 Uiso 1 1 calc R H14C H 0.8007 0.8360 0.0342 0.039 Uiso 1 1 calc R C15 C 0.5453(4) 0.8265(3) 0.1472(2) 0.0326(9) Uani 1 1 d . H15A H 0.5873 0.8714 0.1052 0.049 Uiso 1 1 calc R H15B H 0.5539 0.8586 0.2008 0.049 Uiso 1 1 calc R H15C H 0.4346 0.8120 0.1354 0.049 Uiso 1 1 calc R C16 C 0.4847(4) 0.6463(4) 0.2674(2) 0.0389(10) Uani 1 1 d . H16A H 0.3849 0.6336 0.2393 0.058 Uiso 1 1 calc R H16B H 0.4782 0.7098 0.2970 0.058 Uiso 1 1 calc R H16C H 0.5057 0.5920 0.3062 0.058 Uiso 1 1 calc R Cl1 Cl 1.10948(9) 0.76058(7) 0.18549(5) 0.02672(18) Uani 1 1 d . Cl2 Cl 0.79839(10) 0.85362(6) 0.30336(5) 0.02431(17) Uani 1 1 d . N1 N 1.1220(3) 0.5098(2) 0.43154(18) 0.0249(6) Uani 1 1 d . N2 N 1.1333(4) 0.6845(2) 0.47754(17) 0.0252(6) Uani 1 1 d . N3 N 0.8921(3) 0.5842(2) 0.49975(17) 0.0246(6) Uani 1 1 d . P2 P 0.95213(10) 0.64495(6) 0.34183(5) 0.01791(17) Uani 1 1 d . Rh1 Rh 0.84907(3) 0.705734(17) 0.222750(14) 0.01573(7) 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 0.0234(17) 0.0216(15) 0.0252(16) -0.0043(14) 0.0046(15) 0.0043(14) C2 0.0212(17) 0.0290(17) 0.0215(15) 0.0009(14) -0.0022(14) 0.0026(15) C3 0.0294(18) 0.0208(16) 0.0242(16) 0.0026(13) -0.0086(15) -0.0056(14) C4 0.0209(16) 0.0302(18) 0.0285(18) 0.0025(15) -0.0027(15) 0.0030(15) C5 0.035(2) 0.0254(17) 0.0275(19) 0.0083(15) -0.0002(16) -0.0033(16) C6 0.036(2) 0.0337(19) 0.0175(15) -0.0041(15) -0.0035(15) 0.0085(17) C7 0.0244(17) 0.0237(16) 0.0215(16) -0.0002(14) -0.0047(14) -0.0115(14) C8 0.0198(17) 0.0192(14) 0.0184(14) -0.0047(12) -0.0045(13) -0.0031(14) C9 0.0178(14) 0.0202(14) 0.0170(14) -0.0039(14) -0.0028(12) -0.0019(14) C10 0.0162(15) 0.0287(16) 0.0233(15) -0.0038(13) -0.0055(14) 0.0001(14) C11 0.0139(15) 0.0416(19) 0.0208(17) 0.0027(15) -0.0010(12) -0.0071(14) C12 0.044(2) 0.0257(16) 0.0314(18) 0.0054(18) -0.004(2) -0.0122(16) C13 0.031(2) 0.0259(17) 0.0298(18) -0.0072(15) 0.0004(17) 0.0052(16) C14 0.0317(19) 0.0264(16) 0.0199(15) 0.0011(13) 0.0004(15) -0.0025(15) C15 0.0280(18) 0.040(2) 0.0295(18) -0.0078(16) -0.0085(16) 0.0141(18) C16 0.0199(17) 0.062(3) 0.035(2) 0.006(2) 0.0082(17) -0.0063(18) Cl1 0.0164(4) 0.0355(4) 0.0283(4) -0.0024(4) 0.0037(3) -0.0069(3) Cl2 0.0286(4) 0.0226(4) 0.0217(4) -0.0037(3) 0.0009(3) 0.0025(3) N1 0.0250(16) 0.0224(13) 0.0272(14) 0.0017(11) -0.0007(13) 0.0030(12) N2 0.0279(15) 0.0263(14) 0.0215(13) 0.0011(11) -0.0065(13) -0.0015(13) N3 0.0213(14) 0.0328(15) 0.0198(13) 0.0027(12) 0.0023(12) 0.0007(13) P2 0.0174(4) 0.0191(4) 0.0172(4) -0.0004(3) -0.0010(3) -0.0016(3) Rh1 0.01397(11) 0.01810(11) 0.01511(11) -0.00049(9) 0.00035(10) -0.00118(9) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Rh Rh -1.1178 0.9187 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l -4 1 -3 1 7 2 loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle N1 C1 P2 110.8(2) N1 C1 H1A 109.5 P2 C1 H1A 109.5 N1 C1 H1B 109.5 P2 C1 H1B 109.5 H1A C1 H1B 108.1 N3 C2 P2 111.8(2) N3 C2 H2A 109.3 P2 C2 H2A 109.3 N3 C2 H2B 109.3 P2 C2 H2B 109.3 H2A C2 H2B 107.9 N2 C3 P2 111.7(2) N2 C3 H3A 109.3 P2 C3 H3A 109.3 N2 C3 H3B 109.3 P2 C3 H3B 109.3 H3A C3 H3B 107.9 N2 C4 N1 114.2(3) N2 C4 H4A 108.7 N1 C4 H4A 108.7 N2 C4 H4B 108.7 N1 C4 H4B 108.7 H4A C4 H4B 107.6 N1 C5 N3 114.3(3) N1 C5 H5A 108.7 N3 C5 H5A 108.7 N1 C5 H5B 108.7 N3 C5 H5B 108.7 H5A C5 H5B 107.6 N2 C6 N3 114.8(3) N2 C6 H6A 108.6 N3 C6 H6A 108.6 N2 C6 H6B 108.6 N3 C6 H6B 108.6 H6A C6 H6B 107.5 C8 C7 C11 107.9(3) C8 C7 C12 124.9(3) C11 C7 C12 127.1(3) C8 C7 Rh1 70.21(18) C11 C7 Rh1 69.28(18) C12 C7 Rh1 129.0(2) C7 C8 C9 107.8(3) C7 C8 C13 126.5(3) C9 C8 C13 125.4(3) C7 C8 Rh1 71.19(18) C9 C8 Rh1 73.30(17) C13 C8 Rh1 125.7(2) C10 C9 C8 107.9(3) C10 C9 C14 126.7(3) C8 C9 C14 125.4(3) C10 C9 Rh1 70.98(17) C8 C9 Rh1 67.99(16) C14 C9 Rh1 127.0(2) C9 C10 C11 108.3(3) C9 C10 C15 127.2(3) C11 C10 C15 124.5(3) C9 C10 Rh1 71.95(18) C11 C10 Rh1 67.60(18) C15 C10 Rh1 124.0(2) C7 C11 C10 107.7(3) C7 C11 C16 126.7(3) C10 C11 C16 124.8(3) C7 C11 Rh1 71.82(18) C10 C11 Rh1 73.53(19) C16 C11 Rh1 128.1(2) C7 C12 H12A 109.5 C7 C12 H12B 109.5 H12A C12 H12B 109.5 C7 C12 H12C 109.5 H12A C12 H12C 109.5 H12B C12 H12C 109.5 C8 C13 H13A 109.5 C8 C13 H13B 109.5 H13A C13 H13B 109.5 C8 C13 H13C 109.5 H13A C13 H13C 109.5 H13B C13 H13C 109.5 C9 C14 H14A 109.5 C9 C14 H14B 109.5 H14A C14 H14B 109.5 C9 C14 H14C 109.5 H14A C14 H14C 109.5 H14B C14 H14C 109.5 C10 C15 H15A 109.5 C10 C15 H15B 109.5 H15A C15 H15B 109.5 C10 C15 H15C 109.5 H15A C15 H15C 109.5 H15B C15 H15C 109.5 C11 C16 H16A 109.5 C11 C16 H16B 109.5 H16A C16 H16B 109.5 C11 C16 H16C 109.5 H16A C16 H16C 109.5 H16B C16 H16C 109.5 C5 N1 C4 108.6(3) C5 N1 C1 111.4(3) C4 N1 C1 112.2(3) C4 N2 C6 108.3(3) C4 N2 C3 111.2(3) C6 N2 C3 110.9(3) C5 N3 C6 108.6(3) C5 N3 C2 111.1(3) C6 N3 C2 110.0(3) C2 P2 C3 98.61(16) C2 P2 C1 98.79(16) C3 P2 C1 98.33(16) C2 P2 Rh1 116.61(11) C3 P2 Rh1 116.83(11) C1 P2 Rh1 123.21(11) C11 Rh1 C8 65.29(12) C11 Rh1 C7 38.91(13) C8 Rh1 C7 38.60(12) C11 Rh1 C10 38.88(12) C8 Rh1 C10 64.05(12) C7 Rh1 C10 64.16(13) C11 Rh1 C9 64.20(11) C8 Rh1 C9 38.71(12) C7 Rh1 C9 64.01(12) C10 Rh1 C9 37.07(11) C11 Rh1 P2 110.27(9) C8 Rh1 P2 119.74(9) C7 Rh1 P2 98.13(9) C10 Rh1 P2 147.50(9) C9 Rh1 P2 158.44(9) C11 Rh1 Cl1 157.81(9) C8 Rh1 Cl1 95.39(9) C7 Rh1 Cl1 129.25(10) C10 Rh1 Cl1 124.06(9) C9 Rh1 Cl1 94.01(9) P2 Rh1 Cl1 88.39(4) C11 Rh1 Cl2 100.61(10) C8 Rh1 Cl2 155.00(9) C7 Rh1 Cl2 137.66(10) C10 Rh1 Cl2 91.83(9) C9 Rh1 Cl2 117.26(9) P2 Rh1 Cl2 83.95(4) Cl1 Rh1 Cl2 93.00(3) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance C1 N1 1.470(4) C1 P2 1.849(3) C1 H1A 0.9900 C1 H1B 0.9900 C2 N3 1.480(4) C2 P2 1.841(3) C2 H2A 0.9900 C2 H2B 0.9900 C3 N2 1.471(4) C3 P2 1.845(3) C3 H3A 0.9900 C3 H3B 0.9900 C4 N2 1.460(4) C4 N1 1.467(4) C4 H4A 0.9900 C4 H4B 0.9900 C5 N1 1.461(5) C5 N3 1.468(4) C5 H5A 0.9900 C5 H5B 0.9900 C6 N2 1.467(5) C6 N3 1.472(5) C6 H6A 0.9900 C6 H6B 0.9900 C7 C8 1.427(5) C7 C11 1.431(5) C7 C12 1.507(5) C7 Rh1 2.165(3) C8 C9 1.452(5) C8 C13 1.492(5) C8 Rh1 2.152(3) C9 C10 1.410(4) C9 C14 1.491(4) C9 Rh1 2.224(3) C10 C11 1.447(5) C10 C15 1.492(5) C10 Rh1 2.211(3) C11 C16 1.503(4) C11 Rh1 2.132(3) C12 H12A 0.9800 C12 H12B 0.9800 C12 H12C 0.9800 C13 H13A 0.9800 C13 H13B 0.9800 C13 H13C 0.9800 C14 H14A 0.9800 C14 H14B 0.9800 C14 H14C 0.9800 C15 H15A 0.9800 C15 H15B 0.9800 C15 H15C 0.9800 C16 H16A 0.9800 C16 H16B 0.9800 C16 H16C 0.9800 Cl1 Rh1 2.4104(11) Cl2 Rh1 2.4169(11) P2 Rh1 2.2857(13)