# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full Chem.Commun. _journal_coden_cambridge 0182 _publ_section_title ; o-(Dimesitylboryl)phenylphosphines as Biarylphosphine Cousins: the Showcase of Pd-Catalyzed Suzuki-Miyaura Coupling ; _publ_contact_author_name 'Didier Bourissou' _publ_contact_author_email dbouriss@chimie.ups-tlse.fr loop_ _publ_author_name 'Raluca Malacea' N.Saffon 'Montserrat Gomez' 'Didier Bourissou' #------------------ SECTION 2. COMPOUND(S) DETAILS -------------------------# data_aa04gy1n _database_code_depnum_ccdc_archive 'CCDC 802793' #TrackingRef 'ccdc_deposit - Copie.cif' _audit_creation_date 2009-05-06T16:40:59-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C40 H38 B O3 P Pd' _chemical_formula_sum 'C40 H38 B O3 P Pd' _chemical_formula_weight 714.88 _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 8.2541(16) _cell_length_b 22.531(5) _cell_length_c 17.726(4) _cell_angle_alpha 90 _cell_angle_beta 90.010(11) _cell_angle_gamma 90 _cell_volume 3296.7(12) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 3087 _cell_measurement_theta_min 2.47 _cell_measurement_theta_max 22.56 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description plate _exptl_crystal_colour yellow _exptl_crystal_size_max 0.13 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.02 _exptl_crystal_density_diffrn 1.44 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1472 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.65 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8139 _exptl_absorpt_correction_T_max 0.9853 _exptl_absorpt_process_details 'BRUKER AXS - SADABS' #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_measurement_device_type 'Bruker X8 kappa APEXII CCD' _diffrn_measurement_method 'omega and phi scans' _diffrn_reflns_av_R_equivalents 0.0680 _diffrn_reflns_av_unetI/netI 0.0759 _diffrn_reflns_number 25011 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 27 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 1.46 _diffrn_reflns_theta_max 26.02 _diffrn_reflns_theta_full 26.02 _diffrn_measured_fraction_theta_full 0.995 _diffrn_measured_fraction_theta_max 0.995 _reflns_number_total 6462 _reflns_number_gt 4674 _reflns_threshold_expression >2\s(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'APEX2 v2009-3.0 (BRUKER AXS, Madison, 2009)' _computing_cell_refinement 'APEX2 v2009-3.0 (BRUKER AXS, Madison, 2009)' _computing_data_reduction 'APEX2 v2009-3.0 (BRUKER AXS, Madison, 2009)' _computing_structure_solution 'SIR97 (Altomare et al., 1998)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # STRUCTURE SOLUTION #----------------------------------------------------------------------------# _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom #----------------------------------------------------------------------------# # 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^ > 2\s(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^)+(0.0318P)^2^+5.9537P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_number_reflns 6462 _refine_ls_number_parameters 421 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0783 _refine_ls_R_factor_gt 0.0453 _refine_ls_wR_factor_ref 0.1001 _refine_ls_wR_factor_gt 0.0878 _refine_ls_goodness_of_fit_ref 1.025 _refine_ls_restrained_S_all 1.025 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.525 _refine_diff_density_min -0.687 _refine_diff_density_rms 0.116 #----------------------------------------------------------------------------# # 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' B B 0.0013 0.0007 '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' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Pd Pd -0.9988 1.0072 '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 Pd1 Pd 0.49500(4) 0.284056(13) -0.038189(17) 0.01290(10) Uani 1 1 d . . . P2 P 0.46489(12) 0.19971(4) 0.03253(6) 0.0117(2) Uani 1 1 d . . . O51 O 0.8106(3) 0.31911(12) -0.14366(15) 0.0183(7) Uani 1 1 d . . . O57 O 0.8721(3) 0.22268(13) -0.13179(15) 0.0206(7) Uani 1 1 d . . . O56 O 0.6814(4) 0.40468(13) -0.16909(17) 0.0247(7) Uani 1 1 d . . . C22 C 0.3322(4) 0.26709(17) 0.1469(2) 0.0119(9) Uani 1 1 d . . . C25 C 0.1674(5) 0.17143(18) 0.2148(2) 0.0169(9) Uani 1 1 d . . . H25 H 0.1086 0.1395 0.2366 0.02 Uiso 1 1 calc R . . C26 C 0.2571(5) 0.16257(18) 0.1493(2) 0.0151(9) Uani 1 1 d . . . H26 H 0.2622 0.1241 0.1275 0.018 Uiso 1 1 calc R . . C16 C 0.3786(5) 0.08368(18) -0.0157(2) 0.0169(9) Uani 1 1 d . . . H16 H 0.4498 0.0694 0.0223 0.02 Uiso 1 1 calc R . . C21 C 0.3392(4) 0.20924(17) 0.1157(2) 0.0122(8) Uani 1 1 d . . . C12 C 0.2508(4) 0.16422(18) -0.0802(2) 0.0142(9) Uani 1 1 d . . . H12 H 0.234 0.2056 -0.087 0.017 Uiso 1 1 calc R . . C41 C 0.4951(4) 0.36698(17) 0.1682(2) 0.0118(8) Uani 1 1 d . . . C36 C 0.1868(5) 0.34436(17) 0.0024(2) 0.0151(9) Uani 1 1 d . . . C39 C 0.0682(5) 0.29958(18) 0.0334(2) 0.0190(10) Uani 1 1 d . . . H39A H -0.0346 0.3027 0.006 0.028 Uiso 1 1 calc R . . H39B H 0.0497 0.3075 0.0871 0.028 Uiso 1 1 calc R . . H39C H 0.1125 0.2595 0.0272 0.028 Uiso 1 1 calc R . . C55 C 0.7674(5) 0.25960(19) -0.1374(2) 0.0151(9) Uani 1 1 d . . . C32 C 0.4492(5) 0.39492(17) -0.0059(2) 0.0127(9) Uani 1 1 d . . . C43 C 0.7135(5) 0.38491(18) 0.2567(2) 0.0163(9) Uani 1 1 d . . . H43 H 0.8138 0.3729 0.2781 0.02 Uiso 1 1 calc R . . C13 C 0.1691(5) 0.12427(18) -0.1256(2) 0.0165(9) Uani 1 1 d . . . H13 H 0.0961 0.1382 -0.1631 0.02 Uiso 1 1 calc R . . C1 C 0.6399(4) 0.15739(17) 0.0659(2) 0.0121(9) Uani 1 1 d . . . C54 C 0.5908(5) 0.25492(18) -0.1423(2) 0.0151(9) Uani 1 1 d . . . H54 H 0.5282 0.2197 -0.1384 0.018 Uiso 1 1 calc R . . C45 C 0.4970(5) 0.45442(18) 0.2479(2) 0.0165(9) Uani 1 1 d . . . H45 H 0.4471 0.4902 0.264 0.02 Uiso 1 1 calc R . . C53 C 0.5320(5) 0.31278(18) -0.1538(2) 0.0164(9) Uani 1 1 d . . . H53 H 0.4214 0.3238 -0.1588 0.02 Uiso 1 1 calc R . . B27 B 0.4021(5) 0.3255(2) 0.1104(3) 0.0121(10) Uani 1 1 d . . . C2 C 0.6539(5) 0.13368(17) 0.1379(2) 0.0159(9) Uani 1 1 d . . . H2 H 0.571 0.1407 0.1739 0.019 Uiso 1 1 calc R . . C15 C 0.2975(5) 0.04378(19) -0.0612(2) 0.0197(10) Uani 1 1 d . . . H15 H 0.3136 0.0024 -0.0545 0.024 Uiso 1 1 calc R . . C37 C 0.6237(5) 0.40711(18) 0.0182(2) 0.0162(9) Uani 1 1 d . . . H37A H 0.6844 0.4234 -0.0246 0.024 Uiso 1 1 calc R . . H37B H 0.6745 0.37 0.0348 0.024 Uiso 1 1 calc R . . H37C H 0.6243 0.4357 0.0598 0.024 Uiso 1 1 calc R . . C3 C 0.7880(5) 0.09969(18) 0.1578(2) 0.0172(9) Uani 1 1 d . . . H3 H 0.7971 0.084 0.2074 0.021 Uiso 1 1 calc R . . C42 C 0.6417(4) 0.34972(17) 0.2018(2) 0.0135(9) Uani 1 1 d . . . C23 C 0.2475(4) 0.27348(18) 0.2151(2) 0.0155(9) Uani 1 1 d . . . H23 H 0.2475 0.311 0.2396 0.019 Uiso 1 1 calc R . . C52 C 0.6691(5) 0.35264(19) -0.1567(2) 0.0178(9) Uani 1 1 d . . . C38 C 0.1545(5) 0.4687(2) -0.1415(3) 0.0311(12) Uani 1 1 d . . . H38A H 0.1193 0.5052 -0.1162 0.047 Uiso 1 1 calc R . . H38B H 0.0613 0.4498 -0.1658 0.047 Uiso 1 1 calc R . . H38C H 0.2362 0.4784 -0.1797 0.047 Uiso 1 1 calc R . . C44 C 0.6417(5) 0.43730(18) 0.2810(2) 0.0175(9) Uani 1 1 d . . . C5 C 0.8955(5) 0.11212(19) 0.0335(2) 0.0218(10) Uani 1 1 d . . . H5 H 0.9783 0.1045 -0.0024 0.026 Uiso 1 1 calc R . . C33 C 0.3862(5) 0.43135(18) -0.0610(2) 0.0172(9) Uani 1 1 d . . . H33 H 0.4544 0.4603 -0.0836 0.021 Uiso 1 1 calc R . . C49 C 0.2622(5) 0.44225(18) 0.1602(2) 0.0197(10) Uani 1 1 d . . . H49A H 0.2293 0.4786 0.1865 0.03 Uiso 1 1 calc R . . H49B H 0.1796 0.4116 0.1677 0.03 Uiso 1 1 calc R . . H49C H 0.274 0.4505 0.1062 0.03 Uiso 1 1 calc R . . C46 C 0.4223(5) 0.42084(18) 0.1917(2) 0.0149(9) Uani 1 1 d . . . C4 C 0.9079(5) 0.08890(18) 0.1051(2) 0.0187(9) Uani 1 1 d . . . H4 H 0.9991 0.0654 0.1183 0.022 Uiso 1 1 calc R . . C35 C 0.1308(5) 0.38208(18) -0.0528(2) 0.0190(10) Uani 1 1 d . . . H35 H 0.0227 0.3774 -0.0701 0.023 Uiso 1 1 calc R . . C31 C 0.3502(4) 0.35115(17) 0.0318(2) 0.0121(8) Uani 1 1 d . . . C24 C 0.1644(4) 0.22694(18) 0.2477(2) 0.0159(9) Uani 1 1 d . . . H24 H 0.1049 0.2331 0.293 0.019 Uiso 1 1 calc R . . C47 C 0.7230(5) 0.29241(18) 0.1783(2) 0.0174(9) Uani 1 1 d . . . H47A H 0.8327 0.2909 0.1994 0.026 Uiso 1 1 calc R . . H47B H 0.729 0.2905 0.1231 0.026 Uiso 1 1 calc R . . H47C H 0.6601 0.2586 0.1972 0.026 Uiso 1 1 calc R . . C6 C 0.7633(5) 0.14648(19) 0.0134(2) 0.0180(9) Uani 1 1 d . . . H6 H 0.7562 0.1627 -0.036 0.022 Uiso 1 1 calc R . . C14 C 0.1935(5) 0.06385(19) -0.1163(2) 0.0176(9) Uani 1 1 d . . . H14 H 0.1387 0.0364 -0.1479 0.021 Uiso 1 1 calc R . . C11 C 0.3574(4) 0.14455(17) -0.0248(2) 0.0120(9) Uani 1 1 d . . . C34 C 0.2261(5) 0.42713(19) -0.0845(2) 0.0197(10) Uani 1 1 d . . . C48 C 0.7193(6) 0.4744(2) 0.3414(3) 0.0274(11) Uani 1 1 d . . . H48A H 0.8323 0.4824 0.3279 0.041 Uiso 1 1 calc R . . H48B H 0.7155 0.453 0.3895 0.041 Uiso 1 1 calc R . . H48C H 0.6606 0.512 0.3463 0.041 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 Pd1 0.01376(16) 0.01161(17) 0.01334(16) 0.00030(14) 0.00049(11) -0.00023(14) P2 0.0129(5) 0.0107(5) 0.0116(5) 0.0000(4) 0.0003(4) 0.0001(4) O51 0.0171(15) 0.0181(17) 0.0198(16) -0.0003(13) 0.0010(12) -0.0062(13) O57 0.0201(15) 0.0247(17) 0.0170(15) 0.0031(14) 0.0032(12) 0.0059(14) O56 0.0364(18) 0.0144(17) 0.0234(17) 0.0022(13) 0.0066(14) -0.0014(14) C22 0.0129(19) 0.012(2) 0.0103(19) -0.0005(16) -0.0064(16) 0.0020(17) C25 0.015(2) 0.017(2) 0.019(2) 0.0046(19) 0.0025(17) -0.0025(18) C26 0.016(2) 0.013(2) 0.017(2) -0.0030(18) 0.0008(17) -0.0002(18) C16 0.018(2) 0.015(2) 0.018(2) -0.0008(18) -0.0047(18) 0.0042(18) C21 0.0108(18) 0.015(2) 0.0104(19) 0.0002(17) -0.0031(15) 0.0006(17) C12 0.015(2) 0.013(2) 0.014(2) 0.0040(18) 0.0016(17) -0.0004(18) C41 0.0134(19) 0.010(2) 0.012(2) 0.0010(17) 0.0008(16) -0.0021(17) C36 0.018(2) 0.013(2) 0.014(2) -0.0022(18) -0.0006(17) 0.0031(18) C39 0.0134(19) 0.017(2) 0.027(2) 0.0010(19) -0.0037(18) -0.0021(18) C55 0.018(2) 0.017(2) 0.010(2) 0.0008(18) 0.0012(17) -0.0009(19) C32 0.018(2) 0.008(2) 0.012(2) -0.0062(17) -0.0017(17) -0.0005(17) C43 0.015(2) 0.020(2) 0.014(2) 0.0045(19) -0.0011(17) -0.0073(19) C13 0.016(2) 0.023(2) 0.010(2) 0.0040(18) -0.0005(17) -0.0017(19) C1 0.014(2) 0.009(2) 0.013(2) -0.0012(17) -0.0057(17) -0.0023(17) C54 0.018(2) 0.015(2) 0.012(2) -0.0020(18) 0.0047(17) -0.0014(18) C45 0.022(2) 0.012(2) 0.016(2) -0.0025(18) 0.0032(17) -0.0036(18) C53 0.016(2) 0.024(2) 0.009(2) 0.0012(18) 0.0038(17) 0.0020(19) B27 0.008(2) 0.012(2) 0.016(2) -0.002(2) 0.0016(18) 0.0055(19) C2 0.017(2) 0.015(2) 0.017(2) -0.0016(18) 0.0025(17) -0.0022(18) C15 0.021(2) 0.011(2) 0.026(2) -0.0045(19) -0.0018(19) 0.0013(19) C37 0.017(2) 0.014(2) 0.017(2) -0.0008(18) -0.0032(18) 0.0023(18) C3 0.020(2) 0.014(2) 0.017(2) 0.0020(18) -0.0025(18) 0.0030(18) C42 0.0120(19) 0.012(2) 0.016(2) 0.0057(17) -0.0007(17) -0.0017(17) C23 0.0149(19) 0.016(2) 0.015(2) -0.0068(18) -0.0029(17) 0.0052(18) C52 0.022(2) 0.018(3) 0.012(2) -0.0004(19) 0.0027(18) -0.001(2) C38 0.028(3) 0.030(3) 0.035(3) 0.014(2) -0.011(2) -0.003(2) C44 0.023(2) 0.016(2) 0.014(2) 0.0009(18) -0.0026(18) -0.0107(19) C5 0.018(2) 0.024(2) 0.024(2) -0.002(2) 0.0105(19) -0.003(2) C33 0.022(2) 0.015(2) 0.014(2) 0.0008(18) 0.0024(18) 0.0015(19) C49 0.022(2) 0.014(2) 0.023(2) -0.0060(19) -0.0013(19) 0.0037(19) C46 0.013(2) 0.017(2) 0.015(2) 0.0028(18) 0.0010(17) -0.0040(18) C4 0.014(2) 0.014(2) 0.027(2) -0.0019(19) -0.0021(18) -0.0010(18) C35 0.016(2) 0.020(2) 0.021(2) -0.0036(19) -0.0071(18) 0.0028(19) C31 0.0106(19) 0.010(2) 0.016(2) -0.0051(17) -0.0010(16) 0.0028(17) C24 0.0081(18) 0.027(3) 0.013(2) 0.0023(19) 0.0013(16) -0.0006(18) C47 0.0142(19) 0.018(2) 0.020(2) 0.0035(19) -0.0014(17) 0.0026(18) C6 0.016(2) 0.022(2) 0.017(2) 0.0065(19) 0.0032(17) 0.0025(19) C14 0.014(2) 0.019(2) 0.020(2) -0.0076(19) 0.0001(18) -0.0044(18) C11 0.0116(19) 0.015(2) 0.0093(19) -0.0015(17) 0.0031(16) -0.0033(17) C34 0.025(2) 0.015(2) 0.019(2) 0.0005(19) -0.0065(19) 0.0007(19) C48 0.036(3) 0.021(3) 0.025(3) -0.004(2) -0.008(2) -0.008(2) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 Pd1 C54 2.112(4) . ? Pd1 C53 2.171(4) . ? Pd1 P2 2.2901(11) . ? Pd1 C31 2.292(4) . ? Pd1 C32 2.590(4) . ? P2 C21 1.815(4) . ? P2 C1 1.829(4) . ? P2 C11 1.834(4) . ? O51 C55 1.392(5) . ? O51 C52 1.410(5) . ? O57 C55 1.204(5) . ? O56 C52 1.197(5) . ? C22 C23 1.405(5) . ? C22 C21 1.417(5) . ? C22 B27 1.575(6) . ? C25 C24 1.381(6) . ? C25 C26 1.391(5) . ? C25 H25 0.95 . ? C26 C21 1.386(5) . ? C26 H26 0.95 . ? C16 C15 1.381(6) . ? C16 C11 1.392(5) . ? C16 H16 0.95 . ? C12 C13 1.383(6) . ? C12 C11 1.391(5) . ? C12 H12 0.95 . ? C41 C42 1.404(5) . ? C41 C46 1.417(5) . ? C41 B27 1.585(6) . ? C36 C35 1.375(6) . ? C36 C31 1.455(5) . ? C36 C39 1.509(5) . ? C39 H39A 0.98 . ? C39 H39B 0.98 . ? C39 H39C 0.98 . ? C55 C54 1.464(5) . ? C32 C33 1.378(6) . ? C32 C31 1.445(5) . ? C32 C37 1.527(5) . ? C43 C42 1.388(6) . ? C43 C44 1.389(6) . ? C43 H43 0.95 . ? C13 C14 1.386(6) . ? C13 H13 0.95 . ? C1 C2 1.387(5) . ? C1 C6 1.402(5) . ? C54 C53 1.406(6) . ? C54 H54 0.95 . ? C45 C44 1.385(6) . ? C45 C46 1.394(5) . ? C45 H45 0.95 . ? C53 C52 1.445(6) . ? C53 H53 0.95 . ? B27 C31 1.568(6) . ? C2 C3 1.391(5) . ? C2 H2 0.95 . ? C15 C14 1.376(6) . ? C15 H15 0.95 . ? C37 H37A 0.98 . ? C37 H37B 0.98 . ? C37 H37C 0.98 . ? C3 C4 1.383(6) . ? C3 H3 0.95 . ? C42 C47 1.514(5) . ? C23 C24 1.380(6) . ? C23 H23 0.95 . ? C38 C34 1.499(6) . ? C38 H38A 0.98 . ? C38 H38B 0.98 . ? C38 H38C 0.98 . ? C44 C48 1.502(6) . ? C5 C4 1.377(6) . ? C5 C6 1.384(6) . ? C5 H5 0.95 . ? C33 C34 1.389(6) . ? C33 H33 0.95 . ? C49 C46 1.513(5) . ? C49 H49A 0.98 . ? C49 H49B 0.98 . ? C49 H49C 0.98 . ? C4 H4 0.95 . ? C35 C34 1.402(6) . ? C35 H35 0.95 . ? C24 H24 0.95 . ? C47 H47A 0.98 . ? C47 H47B 0.98 . ? C47 H47C 0.98 . ? C6 H6 0.95 . ? C14 H14 0.95 . ? C48 H48A 0.98 . ? C48 H48B 0.98 . ? C48 H48C 0.98 . ? 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 C54 Pd1 C53 38.30(15) . . ? C54 Pd1 P2 105.12(12) . . ? C53 Pd1 P2 141.21(11) . . ? C54 Pd1 C31 150.84(15) . . ? C53 Pd1 C31 112.83(15) . . ? P2 Pd1 C31 101.20(10) . . ? C54 Pd1 C32 123.19(14) . . ? C53 Pd1 C32 86.65(14) . . ? P2 Pd1 C32 131.56(9) . . ? C31 Pd1 C32 33.72(13) . . ? C21 P2 C1 104.51(18) . . ? C21 P2 C11 104.69(17) . . ? C1 P2 C11 101.99(17) . . ? C21 P2 Pd1 114.10(13) . . ? C1 P2 Pd1 121.59(13) . . ? C11 P2 Pd1 108.15(13) . . ? C55 O51 C52 108.5(3) . . ? C23 C22 C21 116.8(3) . . ? C23 C22 B27 116.8(3) . . ? C21 C22 B27 126.3(3) . . ? C24 C25 C26 119.5(4) . . ? C24 C25 H25 120.2 . . ? C26 C25 H25 120.2 . . ? C21 C26 C25 120.7(4) . . ? C21 C26 H26 119.6 . . ? C25 C26 H26 119.6 . . ? C15 C16 C11 120.8(4) . . ? C15 C16 H16 119.6 . . ? C11 C16 H16 119.6 . . ? C26 C21 C22 120.6(3) . . ? C26 C21 P2 122.6(3) . . ? C22 C21 P2 116.7(3) . . ? C13 C12 C11 120.8(4) . . ? C13 C12 H12 119.6 . . ? C11 C12 H12 119.6 . . ? C42 C41 C46 118.6(4) . . ? C42 C41 B27 121.9(3) . . ? C46 C41 B27 119.4(3) . . ? C35 C36 C31 120.1(4) . . ? C35 C36 C39 117.0(3) . . ? C31 C36 C39 122.8(4) . . ? C36 C39 H39A 109.5 . . ? C36 C39 H39B 109.5 . . ? H39A C39 H39B 109.5 . . ? C36 C39 H39C 109.5 . . ? H39A C39 H39C 109.5 . . ? H39B C39 H39C 109.5 . . ? O57 C55 O51 119.2(4) . . ? O57 C55 C54 132.1(4) . . ? O51 C55 C54 108.6(3) . . ? C33 C32 C31 121.4(4) . . ? C33 C32 C37 116.5(4) . . ? C31 C32 C37 121.8(3) . . ? C33 C32 Pd1 118.2(3) . . ? C31 C32 Pd1 61.7(2) . . ? C37 C32 Pd1 95.6(2) . . ? C42 C43 C44 121.4(4) . . ? C42 C43 H43 119.3 . . ? C44 C43 H43 119.3 . . ? C12 C13 C14 120.0(4) . . ? C12 C13 H13 120 . . ? C14 C13 H13 120 . . ? C2 C1 C6 118.9(4) . . ? C2 C1 P2 124.3(3) . . ? C6 C1 P2 116.7(3) . . ? C53 C54 C55 106.6(4) . . ? C53 C54 Pd1 73.1(2) . . ? C55 C54 Pd1 107.4(3) . . ? C53 C54 H54 126.7 . . ? C55 C54 H54 126.7 . . ? Pd1 C54 H54 89.6 . . ? C44 C45 C46 122.2(4) . . ? C44 C45 H45 118.9 . . ? C46 C45 H45 118.9 . . ? C54 C53 C52 108.1(4) . . ? C54 C53 Pd1 68.6(2) . . ? C52 C53 Pd1 109.2(3) . . ? C54 C53 H53 125.9 . . ? C52 C53 H53 125.9 . . ? Pd1 C53 H53 91.8 . . ? C31 B27 C22 125.0(3) . . ? C31 B27 C41 119.3(3) . . ? C22 B27 C41 113.9(3) . . ? C1 C2 C3 120.8(4) . . ? C1 C2 H2 119.6 . . ? C3 C2 H2 119.6 . . ? C14 C15 C16 120.2(4) . . ? C14 C15 H15 119.9 . . ? C16 C15 H15 119.9 . . ? C32 C37 H37A 109.5 . . ? C32 C37 H37B 109.5 . . ? H37A C37 H37B 109.5 . . ? C32 C37 H37C 109.5 . . ? H37A C37 H37C 109.5 . . ? H37B C37 H37C 109.5 . . ? C4 C3 C2 119.6(4) . . ? C4 C3 H3 120.2 . . ? C2 C3 H3 120.2 . . ? C43 C42 C41 120.4(4) . . ? C43 C42 C47 119.4(3) . . ? C41 C42 C47 120.1(4) . . ? C24 C23 C22 122.0(4) . . ? C24 C23 H23 119 . . ? C22 C23 H23 119 . . ? O56 C52 O51 119.0(4) . . ? O56 C52 C53 132.9(4) . . ? O51 C52 C53 108.0(3) . . ? C34 C38 H38A 109.5 . . ? C34 C38 H38B 109.5 . . ? H38A C38 H38B 109.5 . . ? C34 C38 H38C 109.5 . . ? H38A C38 H38C 109.5 . . ? H38B C38 H38C 109.5 . . ? C45 C44 C43 118.2(4) . . ? C45 C44 C48 121.0(4) . . ? C43 C44 C48 120.8(4) . . ? C4 C5 C6 120.6(4) . . ? C4 C5 H5 119.7 . . ? C6 C5 H5 119.7 . . ? C32 C33 C34 122.1(4) . . ? C32 C33 H33 119 . . ? C34 C33 H33 119 . . ? C46 C49 H49A 109.5 . . ? C46 C49 H49B 109.5 . . ? H49A C49 H49B 109.5 . . ? C46 C49 H49C 109.5 . . ? H49A C49 H49C 109.5 . . ? H49B C49 H49C 109.5 . . ? C45 C46 C41 119.2(4) . . ? C45 C46 C49 118.5(4) . . ? C41 C46 C49 122.3(4) . . ? C5 C4 C3 120.2(4) . . ? C5 C4 H4 119.9 . . ? C3 C4 H4 119.9 . . ? C36 C35 C34 123.0(4) . . ? C36 C35 H35 118.5 . . ? C34 C35 H35 118.5 . . ? C32 C31 C36 115.5(3) . . ? C32 C31 B27 120.6(3) . . ? C36 C31 B27 122.2(3) . . ? C32 C31 Pd1 84.5(2) . . ? C36 C31 Pd1 102.7(2) . . ? B27 C31 Pd1 95.5(2) . . ? C23 C24 C25 120.1(4) . . ? C23 C24 H24 119.9 . . ? C25 C24 H24 119.9 . . ? C42 C47 H47A 109.5 . . ? C42 C47 H47B 109.5 . . ? H47A C47 H47B 109.5 . . ? C42 C47 H47C 109.5 . . ? H47A C47 H47C 109.5 . . ? H47B C47 H47C 109.5 . . ? C5 C6 C1 120.0(4) . . ? C5 C6 H6 120 . . ? C1 C6 H6 120 . . ? C15 C14 C13 119.8(4) . . ? C15 C14 H14 120.1 . . ? C13 C14 H14 120.1 . . ? C12 C11 C16 118.4(4) . . ? C12 C11 P2 118.8(3) . . ? C16 C11 P2 122.9(3) . . ? C33 C34 C35 117.6(4) . . ? C33 C34 C38 122.3(4) . . ? C35 C34 C38 120.1(4) . . ? C44 C48 H48A 109.5 . . ? C44 C48 H48B 109.5 . . ? H48A C48 H48B 109.5 . . ? C44 C48 H48C 109.5 . . ? H48A C48 H48C 109.5 . . ? H48B C48 H48C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C54 Pd1 P2 C21 -165.61(17) . . . . ? C53 Pd1 P2 C21 -149.6(2) . . . . ? C31 Pd1 P2 C21 1.73(16) . . . . ? C32 Pd1 P2 C21 18.50(18) . . . . ? C54 Pd1 P2 C1 67.71(19) . . . . ? C53 Pd1 P2 C1 83.7(2) . . . . ? C31 Pd1 P2 C1 -124.94(18) . . . . ? C32 Pd1 P2 C1 -108.18(19) . . . . ? C54 Pd1 P2 C11 -49.57(17) . . . . ? C53 Pd1 P2 C11 -33.6(2) . . . . ? C31 Pd1 P2 C11 117.77(16) . . . . ? C32 Pd1 P2 C11 134.53(17) . . . . ? C24 C25 C26 C21 -2.1(6) . . . . ? C25 C26 C21 C22 -0.5(6) . . . . ? C25 C26 C21 P2 177.4(3) . . . . ? C23 C22 C21 C26 3.8(5) . . . . ? B27 C22 C21 C26 -172.7(3) . . . . ? C23 C22 C21 P2 -174.2(3) . . . . ? B27 C22 C21 P2 9.3(5) . . . . ? C1 P2 C21 C26 -69.6(3) . . . . ? C11 P2 C21 C26 37.2(4) . . . . ? Pd1 P2 C21 C26 155.3(3) . . . . ? C1 P2 C21 C22 108.4(3) . . . . ? C11 P2 C21 C22 -144.8(3) . . . . ? Pd1 P2 C21 C22 -26.8(3) . . . . ? C52 O51 C55 O57 174.5(3) . . . . ? C52 O51 C55 C54 -3.3(4) . . . . ? C54 Pd1 C32 C33 41.6(4) . . . . ? C53 Pd1 C32 C33 29.4(3) . . . . ? P2 Pd1 C32 C33 -143.2(3) . . . . ? C31 Pd1 C32 C33 -112.5(4) . . . . ? C54 Pd1 C32 C31 154.1(2) . . . . ? C53 Pd1 C32 C31 142.0(2) . . . . ? P2 Pd1 C32 C31 -30.6(3) . . . . ? C54 Pd1 C32 C37 -82.6(3) . . . . ? C53 Pd1 C32 C37 -94.8(2) . . . . ? P2 Pd1 C32 C37 92.6(2) . . . . ? C31 Pd1 C32 C37 123.3(3) . . . . ? C11 C12 C13 C14 -0.3(6) . . . . ? C21 P2 C1 C2 6.6(4) . . . . ? C11 P2 C1 C2 -102.3(4) . . . . ? Pd1 P2 C1 C2 137.4(3) . . . . ? C21 P2 C1 C6 -176.4(3) . . . . ? C11 P2 C1 C6 74.8(3) . . . . ? Pd1 P2 C1 C6 -45.5(4) . . . . ? O57 C55 C54 C53 -175.7(4) . . . . ? O51 C55 C54 C53 1.8(4) . . . . ? O57 C55 C54 Pd1 107.3(4) . . . . ? O51 C55 C54 Pd1 -75.3(3) . . . . ? P2 Pd1 C54 C53 163.9(2) . . . . ? C31 Pd1 C54 C53 10.0(4) . . . . ? C32 Pd1 C54 C53 -19.8(3) . . . . ? C53 Pd1 C54 C55 102.5(4) . . . . ? P2 Pd1 C54 C55 -93.6(3) . . . . ? C31 Pd1 C54 C55 112.6(3) . . . . ? C32 Pd1 C54 C55 82.7(3) . . . . ? C55 C54 C53 C52 0.4(4) . . . . ? Pd1 C54 C53 C52 104.1(3) . . . . ? C55 C54 C53 Pd1 -103.6(3) . . . . ? P2 Pd1 C53 C54 -25.4(3) . . . . ? C31 Pd1 C53 C54 -174.7(2) . . . . ? C32 Pd1 C53 C54 163.5(2) . . . . ? C54 Pd1 C53 C52 -102.6(4) . . . . ? P2 Pd1 C53 C52 -127.9(2) . . . . ? C31 Pd1 C53 C52 82.7(3) . . . . ? C32 Pd1 C53 C52 60.9(3) . . . . ? C23 C22 B27 C31 -117.1(4) . . . . ? C21 C22 B27 C31 59.4(5) . . . . ? C23 C22 B27 C41 46.9(5) . . . . ? C21 C22 B27 C41 -136.7(4) . . . . ? C42 C41 B27 C31 -128.0(4) . . . . ? C46 C41 B27 C31 57.4(5) . . . . ? C42 C41 B27 C22 67.0(5) . . . . ? C46 C41 B27 C22 -107.6(4) . . . . ? C6 C1 C2 C3 0.1(6) . . . . ? P2 C1 C2 C3 177.1(3) . . . . ? C11 C16 C15 C14 -0.3(6) . . . . ? C1 C2 C3 C4 -0.7(6) . . . . ? C44 C43 C42 C41 1.2(6) . . . . ? C44 C43 C42 C47 -178.8(4) . . . . ? C46 C41 C42 C43 -0.2(6) . . . . ? B27 C41 C42 C43 -174.8(4) . . . . ? C46 C41 C42 C47 179.9(3) . . . . ? B27 C41 C42 C47 5.2(6) . . . . ? C21 C22 C23 C24 -4.8(6) . . . . ? B27 C22 C23 C24 172.0(3) . . . . ? C55 O51 C52 O56 -174.7(4) . . . . ? C55 O51 C52 C53 3.6(4) . . . . ? C54 C53 C52 O56 175.5(4) . . . . ? Pd1 C53 C52 O56 -111.5(5) . . . . ? C54 C53 C52 O51 -2.4(4) . . . . ? Pd1 C53 C52 O51 70.5(3) . . . . ? C46 C45 C44 C43 0.1(6) . . . . ? C46 C45 C44 C48 -179.9(4) . . . . ? C42 C43 C44 C45 -1.2(6) . . . . ? C42 C43 C44 C48 178.9(4) . . . . ? C31 C32 C33 C34 -1.6(6) . . . . ? C37 C32 C33 C34 -176.1(4) . . . . ? Pd1 C32 C33 C34 70.9(5) . . . . ? C44 C45 C46 C41 0.9(6) . . . . ? C44 C45 C46 C49 178.5(4) . . . . ? C42 C41 C46 C45 -0.9(5) . . . . ? B27 C41 C46 C45 173.9(4) . . . . ? C42 C41 C46 C49 -178.4(4) . . . . ? B27 C41 C46 C49 -3.6(6) . . . . ? C6 C5 C4 C3 0.0(6) . . . . ? C2 C3 C4 C5 0.6(6) . . . . ? C31 C36 C35 C34 1.6(6) . . . . ? C39 C36 C35 C34 177.6(4) . . . . ? C33 C32 C31 C36 6.0(5) . . . . ? C37 C32 C31 C36 -179.8(3) . . . . ? Pd1 C32 C31 C36 -101.5(3) . . . . ? C33 C32 C31 B27 -159.3(4) . . . . ? C37 C32 C31 B27 14.9(5) . . . . ? Pd1 C32 C31 B27 93.2(3) . . . . ? C33 C32 C31 Pd1 107.5(3) . . . . ? C37 C32 C31 Pd1 -78.3(3) . . . . ? C35 C36 C31 C32 -6.0(5) . . . . ? C39 C36 C31 C32 178.2(4) . . . . ? C35 C36 C31 B27 159.1(4) . . . . ? C39 C36 C31 B27 -16.7(6) . . . . ? C35 C36 C31 Pd1 -95.9(4) . . . . ? C39 C36 C31 Pd1 88.3(4) . . . . ? C22 B27 C31 C32 -163.3(4) . . . . ? C41 B27 C31 C32 33.5(5) . . . . ? C22 B27 C31 C36 32.4(6) . . . . ? C41 B27 C31 C36 -130.8(4) . . . . ? C22 B27 C31 Pd1 -76.4(4) . . . . ? C41 B27 C31 Pd1 120.4(3) . . . . ? C54 Pd1 C31 C32 -48.6(4) . . . . ? C53 Pd1 C31 C32 -41.9(3) . . . . ? P2 Pd1 C31 C32 157.1(2) . . . . ? C54 Pd1 C31 C36 66.3(4) . . . . ? C53 Pd1 C31 C36 73.1(3) . . . . ? P2 Pd1 C31 C36 -87.9(2) . . . . ? C32 Pd1 C31 C36 114.9(4) . . . . ? C54 Pd1 C31 B27 -168.9(3) . . . . ? C53 Pd1 C31 B27 -162.2(2) . . . . ? P2 Pd1 C31 B27 36.8(2) . . . . ? C32 Pd1 C31 B27 -120.3(3) . . . . ? C22 C23 C24 C25 2.4(6) . . . . ? C26 C25 C24 C23 1.2(6) . . . . ? C4 C5 C6 C1 -0.6(6) . . . . ? C2 C1 C6 C5 0.6(6) . . . . ? P2 C1 C6 C5 -176.6(3) . . . . ? C16 C15 C14 C13 -0.6(6) . . . . ? C12 C13 C14 C15 0.9(6) . . . . ? C13 C12 C11 C16 -0.6(6) . . . . ? C13 C12 C11 P2 179.0(3) . . . . ? C15 C16 C11 C12 0.9(6) . . . . ? C15 C16 C11 P2 -178.7(3) . . . . ? C21 P2 C11 C12 93.5(3) . . . . ? C1 P2 C11 C12 -157.8(3) . . . . ? Pd1 P2 C11 C12 -28.5(3) . . . . ? C21 P2 C11 C16 -86.9(3) . . . . ? C1 P2 C11 C16 21.7(4) . . . . ? Pd1 P2 C11 C16 151.0(3) . . . . ? C32 C33 C34 C35 -3.1(6) . . . . ? C32 C33 C34 C38 176.7(4) . . . . ? C36 C35 C34 C33 3.1(6) . . . . ? C36 C35 C34 C38 -176.7(4) . . . . ? # The following lines are used to test the character set of files sent by # network email or other means. They are not part of the CIF data set # abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789 # !@#$%^&*()_+{}:"~<>?|\-=[];'`,./ # END of CIF