#------------------------------------------------------------------------------ #$Date: 2015-01-23 12:30:19 +0000 (Fri, 23 Jan 2015) $ #$Revision: 130086 $ #$URL: svn://www.crystallography.net/cod/cif/4/07/55/4075517.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_4075517 loop_ _publ_author_name 'Todd, Michael A.' 'Grachan, Melissa L.' 'Sabat, Michal' 'Myers, William H.' 'Harman, W. Dean' _publ_section_title ; Common Electrophilic Addition Reactions at the Phenol Ring:  The Chemistry of TpW(NO)(PMe3)(\h2-phenol) ; _journal_issue 16 _journal_name_full Organometallics _journal_page_first 3948 _journal_paper_doi 10.1021/om060339f _journal_volume 25 _journal_year 2006 _chemical_formula_sum 'C25 H29 B N7 O2 P W' _chemical_formula_weight 685.18 _chemical_name_systematic ; ? ; _space_group_IT_number 14 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2yn' _symmetry_space_group_name_H-M 'P 1 21/n 1' _atom_sites_solution_hydrogens difmap _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-97 _cell_angle_alpha 90.00 _cell_angle_beta 94.9550(10) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 10.0602(6) _cell_length_b 10.2513(6) _cell_length_c 25.4342(16) _cell_measurement_reflns_used 5764 _cell_measurement_temperature 153(2) _cell_measurement_theta_max 31.819 _cell_measurement_theta_min 2.555 _cell_volume 2613.2(3) _computing_cell_refinement 'Bruker SMART' _computing_data_collection 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _diffrn_ambient_temperature 153(2) _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.998 _diffrn_measurement_device_type 'Bruker SMART APEX CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0604 _diffrn_reflns_av_sigmaI/netI 0.0970 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_l_max 37 _diffrn_reflns_limit_l_min -38 _diffrn_reflns_number 35516 _diffrn_reflns_theta_full 32.53 _diffrn_reflns_theta_max 32.53 _diffrn_reflns_theta_min 1.61 _exptl_absorpt_coefficient_mu 4.519 _exptl_absorpt_correction_T_max 0.801927 _exptl_absorpt_correction_T_min 0.679851 _exptl_absorpt_correction_type empirical _exptl_absorpt_process_details 'Bruker SADABS' _exptl_crystal_colour yellow _exptl_crystal_density_diffrn 1.742 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description needle _exptl_crystal_F_000 1352 _exptl_crystal_size_max 0.29 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.09 _refine_diff_density_max 2.334 _refine_diff_density_min -1.298 _refine_diff_density_rms 0.156 _refine_ls_extinction_coef none _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 0.811 _refine_ls_hydrogen_treatment allref _refine_ls_matrix_type full _refine_ls_number_parameters 438 _refine_ls_number_reflns 9460 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 0.811 _refine_ls_R_factor_all 0.0665 _refine_ls_R_factor_gt 0.0387 _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^)+(0.0204P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0622 _refine_ls_wR_factor_ref 0.0665 _reflns_number_gt 6318 _reflns_number_total 9460 _reflns_threshold_expression >2sigma(I) _[local]_cod_data_source_file om060339fsi20060417_015322.cif _[local]_cod_data_source_block c25h29bn7o2pw _[local]_cod_cif_authors_sg_H-M P2(1)/n _cod_depositor_comments ; The following automatic conversions were performed: '_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic' according to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29. Automatic conversion script Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana The following automatic conversions were performed: '_exptl_crystal_density_meas' value 'not measured' was changed to '?' - the value is perceived as not measured. Automatic conversion script Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas ; _cod_database_code 4075517 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' 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 W W 0.088448(15) 0.389778(15) 0.136508(6) 0.01770(4) Uani 1 1 d . P1 P 0.13731(12) 0.15361(11) 0.12038(4) 0.0281(2) Uani 1 1 d . O1 O 0.0907(3) 0.7443(3) 0.06797(13) 0.0387(8) Uani 1 1 d . O2 O 0.3738(3) 0.4339(3) 0.17399(12) 0.0352(7) Uani 1 1 d . N1 N -0.1270(3) 0.3400(3) 0.11738(12) 0.0228(7) Uani 1 1 d . N2 N -0.2171(3) 0.3580(3) 0.15409(12) 0.0228(7) Uani 1 1 d . N3 N 0.0570(3) 0.3139(3) 0.21466(12) 0.0235(7) Uani 1 1 d . N4 N -0.0625(3) 0.3218(3) 0.23595(13) 0.0255(8) Uani 1 1 d . N5 N 0.0032(3) 0.5589(3) 0.17581(12) 0.0208(7) Uani 1 1 d . N6 N -0.1048(3) 0.5438(3) 0.20503(13) 0.0221(7) Uani 1 1 d . N7 N 0.2571(3) 0.4208(3) 0.15732(12) 0.0205(7) Uani 1 1 d . C1 C 0.1417(4) 0.6360(4) 0.06557(15) 0.0249(9) Uani 1 1 d . C2 C 0.2899(4) 0.6240(4) 0.06074(14) 0.0276(9) Uani 1 1 d . C3 C 0.3391(4) 0.4986(4) 0.04512(16) 0.0261(9) Uani 1 1 d . C4 C 0.2604(4) 0.3943(5) 0.03874(15) 0.0272(9) Uani 1 1 d . C5 C 0.1210(4) 0.3945(4) 0.05074(15) 0.0234(8) Uani 1 1 d . C6 C 0.0658(4) 0.5170(4) 0.06496(16) 0.0225(9) Uani 1 1 d . C7 C 0.3586(5) 0.7371(5) 0.06721(17) 0.0315(10) Uani 1 1 d . C8 C 0.5045(5) 0.7593(5) 0.06992(17) 0.0333(10) Uani 1 1 d . C9 C 0.6049(6) 0.6672(5) 0.08876(18) 0.0380(12) Uani 1 1 d . C10 C 0.7279(5) 0.6931(5) 0.09284(17) 0.0397(12) Uani 1 1 d . H10 H 0.7886 0.6289 0.1046 0.048 Uiso 1 1 calc R C11 C 0.7749(5) 0.8166(6) 0.0800(2) 0.0491(14) Uani 1 1 d . H11 H 0.8662 0.8328 0.0826 0.059 Uiso 1 1 calc R C12 C 0.6861(4) 0.9147(4) 0.0635(2) 0.0394(12) Uani 1 1 d . H12 H 0.7155 0.9985 0.0566 0.047 Uiso 1 1 calc R C13 C 0.5516(5) 0.8829(5) 0.0578(2) 0.0450(12) Uani 1 1 d . C14 C -0.3388(4) 0.3291(4) 0.13281(19) 0.0303(10) Uani 1 1 d . C15 C -0.3323(4) 0.2921(5) 0.08163(19) 0.0327(11) Uani 1 1 d . C16 C -0.1983(4) 0.3004(4) 0.07359(17) 0.0253(9) Uani 1 1 d . C17 C -0.0465(5) 0.2759(5) 0.28559(17) 0.0333(11) Uani 1 1 d . C18 C 0.0816(5) 0.2380(5) 0.29653(18) 0.0368(12) Uani 1 1 d . C19 C 0.1425(5) 0.2632(5) 0.25163(18) 0.0312(10) Uani 1 1 d . C20 C -0.1190(4) 0.6530(4) 0.23224(17) 0.0278(10) Uani 1 1 d . C21 C -0.0249(5) 0.7398(4) 0.22189(17) 0.0313(10) Uani 1 1 d . C22 C 0.0490(4) 0.6782(4) 0.18614(17) 0.0253(9) Uani 1 1 d . C23 C 0.0969(6) 0.0828(5) 0.0557(2) 0.0380(13) Uani 1 1 d . C24 C 0.3116(6) 0.1116(7) 0.1353(3) 0.0529(16) Uani 1 1 d . C25 C 0.0494(8) 0.0407(5) 0.1592(2) 0.0515(16) Uani 1 1 d . B B -0.1714(5) 0.4103(5) 0.20924(19) 0.0259(10) Uani 1 1 d . H1B H -0.251(3) 0.424(3) 0.2313(12) 0.006(9) Uiso 1 1 d . H3 H 0.428(4) 0.494(4) 0.0397(15) 0.024(11) Uiso 1 1 d . H4 H 0.293(4) 0.320(4) 0.0294(17) 0.041(14) Uiso 1 1 d . H5 H 0.063(3) 0.340(3) 0.0349(13) 0.014(10) Uiso 1 1 d . H6 H -0.016(3) 0.528(3) 0.0578(14) 0.010(10) Uiso 1 1 d . H7 H 0.289(5) 0.811(5) 0.0695(19) 0.069(17) Uiso 1 1 d . H9 H 0.578(4) 0.593(4) 0.0920(16) 0.021(12) Uiso 1 1 d . H13 H 0.491(5) 0.947(5) 0.0478(19) 0.056(16) Uiso 1 1 d . H14 H -0.402(3) 0.335(3) 0.1503(13) 0.009(10) Uiso 1 1 d . H15 H -0.390(4) 0.273(3) 0.0586(14) 0.014(10) Uiso 1 1 d . H16 H -0.155(3) 0.278(3) 0.0472(13) 0.005(9) Uiso 1 1 d . H17 H -0.119(4) 0.279(4) 0.3055(15) 0.026(12) Uiso 1 1 d . H18 H 0.114(4) 0.200(4) 0.3226(15) 0.018(11) Uiso 1 1 d . H19 H 0.218(4) 0.253(4) 0.2441(15) 0.021(12) Uiso 1 1 d . H20 H -0.182(4) 0.655(4) 0.2504(15) 0.022(11) Uiso 1 1 d . H21 H -0.016(4) 0.820(4) 0.2359(15) 0.021(11) Uiso 1 1 d . H22 H 0.119(4) 0.703(4) 0.1727(17) 0.040(14) Uiso 1 1 d . H23A H 0.134(4) 0.124(4) 0.0346(17) 0.031(14) Uiso 1 1 d . H23B H 0.005(5) 0.094(4) 0.0440(17) 0.038(14) Uiso 1 1 d . H23C H 0.111(4) -0.012(5) 0.0596(17) 0.042(14) Uiso 1 1 d . H24A H 0.344(5) 0.135(5) 0.1702(19) 0.049(16) Uiso 1 1 d . H24B H 0.318(5) 0.021(5) 0.1336(19) 0.054(16) Uiso 1 1 d . H24C H 0.361(7) 0.135(7) 0.117(3) 0.10(3) Uiso 1 1 d . H25A H -0.052(7) 0.053(6) 0.157(3) 0.12(3) Uiso 1 1 d . H25B H 0.080(4) -0.041(5) 0.1444(17) 0.039(13) Uiso 1 1 d . H25C H 0.084(5) 0.055(5) 0.195(2) 0.058(17) Uiso 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 W 0.01825(7) 0.01840(7) 0.01668(7) 0.00159(8) 0.00294(5) -0.00038(8) P1 0.0334(6) 0.0210(5) 0.0301(6) -0.0002(5) 0.0035(5) 0.0003(5) O1 0.042(2) 0.0259(17) 0.049(2) 0.0048(15) 0.0081(16) 0.0006(15) O2 0.0212(16) 0.0407(19) 0.0429(19) 0.0009(15) -0.0026(14) -0.0043(13) N1 0.0241(18) 0.0245(17) 0.0202(17) 0.0028(14) 0.0035(14) -0.0004(14) N2 0.0194(17) 0.0247(19) 0.0246(17) 0.0028(14) 0.0036(14) -0.0035(13) N3 0.0228(18) 0.0255(18) 0.0224(17) 0.0059(14) 0.0030(14) 0.0041(14) N4 0.0235(18) 0.0318(19) 0.0217(18) 0.0043(15) 0.0058(14) -0.0043(15) N5 0.0212(17) 0.0203(17) 0.0215(17) 0.0001(13) 0.0050(14) -0.0012(14) N6 0.0177(17) 0.0253(18) 0.0241(18) 0.0007(14) 0.0061(14) 0.0003(14) N7 0.0205(17) 0.0218(18) 0.0199(17) 0.0020(13) 0.0055(13) -0.0013(13) C1 0.039(2) 0.020(2) 0.0172(19) 0.0035(15) 0.0073(17) -0.0006(17) C2 0.033(2) 0.033(2) 0.0170(19) 0.0038(18) 0.0040(16) -0.011(2) C3 0.028(2) 0.032(2) 0.020(2) 0.0016(18) 0.0114(18) -0.0009(19) C4 0.035(2) 0.027(2) 0.021(2) -0.001(2) 0.0089(17) -0.001(2) C5 0.026(2) 0.023(2) 0.0209(19) 0.0007(18) 0.0002(16) -0.0078(19) C6 0.022(2) 0.025(2) 0.020(2) 0.0040(17) 0.0020(17) 0.0035(18) C7 0.036(3) 0.035(3) 0.023(2) 0.0047(19) 0.006(2) 0.007(2) C8 0.035(3) 0.037(3) 0.027(2) -0.003(2) 0.004(2) -0.001(2) C9 0.066(4) 0.026(3) 0.023(2) -0.003(2) 0.011(2) 0.002(3) C10 0.040(3) 0.054(3) 0.024(2) -0.008(2) -0.006(2) 0.026(3) C11 0.027(3) 0.070(4) 0.051(3) -0.019(3) 0.006(2) -0.010(3) C12 0.032(3) 0.024(3) 0.065(3) 0.003(2) 0.022(2) -0.0013(19) C13 0.046(3) 0.033(3) 0.056(3) 0.000(3) 0.006(3) 0.004(3) C14 0.019(2) 0.030(2) 0.042(3) 0.004(2) 0.005(2) -0.0060(19) C15 0.022(2) 0.041(3) 0.034(3) -0.001(2) -0.004(2) -0.008(2) C16 0.027(2) 0.024(2) 0.025(2) 0.0016(18) 0.0026(18) -0.0003(18) C17 0.039(3) 0.041(3) 0.021(2) 0.006(2) 0.008(2) -0.008(2) C18 0.039(3) 0.050(3) 0.022(2) 0.013(2) 0.004(2) 0.007(2) C19 0.024(2) 0.043(3) 0.027(2) 0.009(2) 0.0024(19) 0.003(2) C20 0.026(2) 0.030(2) 0.028(2) -0.0047(18) 0.0104(19) 0.0032(19) C21 0.037(3) 0.027(2) 0.031(2) -0.011(2) 0.006(2) 0.002(2) C22 0.025(2) 0.025(2) 0.026(2) -0.0010(18) 0.0020(18) -0.0052(19) C23 0.059(4) 0.019(3) 0.037(3) -0.004(2) 0.008(3) -0.003(2) C24 0.044(3) 0.043(3) 0.071(4) -0.015(4) -0.004(3) 0.021(3) C25 0.091(5) 0.022(3) 0.044(3) -0.005(2) 0.021(3) -0.008(3) B 0.024(2) 0.028(3) 0.027(2) 0.002(2) 0.0092(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' B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' W W -0.8490 6.8722 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle N7 W N3 90.13(13) N7 W N5 97.11(13) N3 W N5 77.01(12) N7 W C5 94.07(14) N3 W C5 160.36(14) N5 W C5 121.31(14) N7 W C6 99.61(15) N3 W C6 159.55(14) N5 W C6 83.93(13) C5 W C6 37.38(14) N7 W N1 174.49(12) N3 W N1 84.43(12) N5 W N1 82.58(12) C5 W N1 90.77(13) C6 W N1 85.84(14) N7 W P1 91.50(10) N3 W P1 81.43(9) N5 W P1 156.75(9) C5 W P1 79.29(12) C6 W P1 115.94(11) N1 W P1 86.80(9) C25 P1 C23 99.1(3) C25 P1 C24 104.1(4) C23 P1 C24 103.4(3) C25 P1 W 114.7(2) C23 P1 W 120.18(18) C24 P1 W 113.2(2) C16 N1 N2 105.7(3) C16 N1 W 133.7(3) N2 N1 W 120.4(2) C14 N2 N1 109.5(3) C14 N2 B 130.0(4) N1 N2 B 120.5(3) C19 N3 N4 106.4(3) C19 N3 W 130.5(3) N4 N3 W 122.9(2) C17 N4 N3 108.3(3) C17 N4 B 130.2(4) N3 N4 B 118.7(3) C22 N5 N6 105.9(3) C22 N5 W 132.2(3) N6 N5 W 120.8(2) C20 N6 N5 108.2(3) C20 N6 B 130.4(3) N5 N6 B 120.5(3) O2 N7 W 175.1(3) O1 C1 C6 123.0(4) O1 C1 C2 119.8(4) C6 C1 C2 117.2(4) C7 C2 C3 127.7(4) C7 C2 C1 114.7(4) C3 C2 C1 117.3(4) C4 C3 C2 122.2(4) C3 C4 C5 123.0(4) C6 C5 C4 117.0(4) C6 C5 W 71.3(2) C4 C5 W 115.3(3) C5 C6 C1 122.0(4) C5 C6 W 71.3(2) C1 C6 W 118.0(3) C2 C7 C8 129.2(4) C13 C8 C9 115.4(5) C13 C8 C7 118.9(4) C9 C8 C7 125.5(4) C10 C9 C8 123.1(5) C9 C10 C11 121.4(5) C12 C11 C10 120.3(4) C11 C12 C13 117.3(4) C12 C13 C8 122.5(5) N2 C14 C15 109.4(4) C14 C15 C16 104.6(4) N1 C16 C15 110.8(4) N4 C17 C18 109.2(4) C17 C18 C19 105.2(4) N3 C19 C18 110.9(4) N6 C20 C21 110.3(4) C20 C21 C22 104.8(4) N5 C22 C21 110.8(4) N6 B N2 110.3(3) N6 B N4 105.0(3) N2 B N4 110.1(3) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance W N7 1.762(3) W N3 2.183(3) W N5 2.211(3) W C5 2.234(4) W C6 2.234(4) W N1 2.239(3) W P1 2.5112(11) P1 C25 1.802(6) P1 C23 1.812(5) P1 C24 1.813(6) O1 C1 1.227(4) O2 N7 1.220(4) N1 C16 1.335(5) N1 N2 1.369(4) N2 C14 1.329(5) N2 B 1.534(6) N3 C19 1.325(5) N3 N4 1.363(4) N4 C17 1.344(5) N4 B 1.535(6) N5 C22 1.326(5) N5 N6 1.376(4) N6 C20 1.330(5) N6 B 1.533(6) C1 C6 1.438(5) C1 C2 1.512(6) C2 C7 1.352(6) C2 C3 1.446(6) C3 C4 1.332(6) C4 C5 1.461(5) C5 C6 1.432(6) C7 C8 1.481(6) C8 C13 1.396(6) C8 C9 1.434(7) C9 C10 1.261(7) C10 C11 1.400(7) C11 C12 1.386(6) C12 C13 1.388(6) C14 C15 1.363(6) C15 C16 1.383(6) C17 C18 1.352(6) C18 C19 1.366(6) C20 C21 1.342(6) C21 C22 1.377(6)