#------------------------------------------------------------------------------ #$Date: 2014-07-11 19:33:45 +0100 (Fri, 11 Jul 2014) $ #$Revision: 120075 $ #$URL: svn://www.crystallography.net/cod/cif/4/07/55/4075545.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_4075545 loop_ _publ_author_name 'Ionkin, Alex S.' 'Marshall, William J.' 'Fish, Brian M.' _publ_section_title ; Divalent Germanium and Tin Compounds Stabilized by Sterically Bulky P∧O, PO∧O, PS∧O, and PN∧O Ligands:  Synthesis and First Insights into Catalytic Application to Polyurethane Systems† ; _journal_issue 17 _journal_name_full Organometallics _journal_page_first 4170 _journal_volume 25 _journal_year 2006 _chemical_formula_sum 'C20 H31 F12 Ge N O2 P2' _chemical_formula_weight 679.99 _chemical_name_systematic ; ? ; _space_group_IT_number 14 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_space_group_name_H-M 'P 1 21/c 1' _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 107.053(4) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 14.454(2) _cell_length_b 9.5410(17) _cell_length_c 20.829(4) _cell_measurement_temperature 293(2) _cell_volume 2746.1(8) _computing_cell_refinement 'Bruker XSCANS' _computing_data_collection 'Bruker XSCANS' _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 293(2) _diffrn_measured_fraction_theta_full 0.994 _diffrn_measured_fraction_theta_max 0.994 _diffrn_measurement_device_type 'Bruker P4' _diffrn_measurement_method '\w 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 0.0953 _diffrn_reflns_av_sigmaI/netI 0.1140 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_number 16702 _diffrn_reflns_theta_full 26.42 _diffrn_reflns_theta_max 26.42 _diffrn_reflns_theta_min 2.05 _exptl_absorpt_coefficient_mu 1.333 _exptl_absorpt_correction_type none _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.645 _exptl_crystal_density_method 'not measured' _exptl_crystal_description 'irregular block' _exptl_crystal_F_000 1376 _exptl_crystal_size_max 0.14 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.02 _refine_diff_density_max 0.800 _refine_diff_density_min -0.624 _refine_diff_density_rms 0.114 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 0.963 _refine_ls_hydrogen_treatment riding _refine_ls_matrix_type full _refine_ls_number_parameters 369 _refine_ls_number_reflns 5597 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 0.963 _refine_ls_R_factor_all 0.1225 _refine_ls_R_factor_gt 0.0575 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0640P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1191 _refine_ls_wR_factor_ref 0.1468 _reflns_number_gt 3180 _reflns_number_total 5597 _reflns_threshold_expression >2sigma(I) _[local]_cod_data_source_file om060355csi20060421_013607.cif _[local]_cod_data_source_block 05156 _[local]_cod_cif_authors_sg_H-M P2(1)/c _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 ; _cod_database_code 4075545 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' 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 Ge1 Ge 0.24204(4) 0.47389(6) 0.15314(3) 0.02571(17) Uani 1 1 d . P1 P 0.12105(10) 0.54853(17) 0.06093(7) 0.0308(4) Uani 1 1 d . F1 F 0.4030(3) 0.5397(4) 0.02800(19) 0.0564(10) Uani 1 1 d . C1 C 0.1973(5) 0.4952(8) 0.0064(3) 0.0394(16) Uani 1 1 d . O1 O 0.3168(2) 0.3959(4) 0.10607(16) 0.0303(9) Uani 1 1 d . P2 P 0.32939(9) 0.51843(15) 0.29647(6) 0.0250(3) Uani 1 1 d . F2 F 0.4320(2) 0.3203(4) 0.02532(17) 0.0488(10) Uani 1 1 d . O2 O 0.2040(3) 0.3149(4) 0.18650(17) 0.0326(9) Uani 1 1 d . C2 C 0.2779(4) 0.3887(6) 0.0365(2) 0.0293(13) Uani 1 1 d . F3 F 0.3327(3) 0.4195(4) -0.06029(16) 0.0531(10) Uani 1 1 d . N1 N 0.3089(3) 0.5727(5) 0.2222(2) 0.0275(10) Uani 1 1 d . C3 C 0.3613(4) 0.4170(7) 0.0067(3) 0.0378(14) Uani 1 1 d . F4 F 0.2096(3) 0.2158(4) -0.04750(17) 0.0574(10) Uani 1 1 d . C4 C 0.2386(4) 0.2401(7) 0.0184(3) 0.0380(14) Uani 1 1 d . F5 F 0.3034(3) 0.1411(4) 0.04598(19) 0.0533(10) Uani 1 1 d . C5 C 0.1331(4) 0.7446(6) 0.0637(3) 0.0359(14) Uani 1 1 d . F6 F 0.1627(2) 0.2187(4) 0.04131(18) 0.0519(10) Uani 1 1 d . C6 C 0.0755(5) 0.7958(7) 0.1095(3) 0.0551(19) Uani 1 1 d . H6A H 0.0700 0.8960 0.1067 0.083 Uiso 1 1 calc R H6B H 0.1081 0.7690 0.1550 0.083 Uiso 1 1 calc R H6C H 0.0121 0.7547 0.0958 0.083 Uiso 1 1 calc R F7 F 0.0788(2) 0.5161(4) 0.21473(17) 0.0490(9) Uani 1 1 d . C7 C 0.2367(4) 0.8007(7) 0.0886(3) 0.0494(17) Uani 1 1 d . H7A H 0.2362 0.9005 0.0824 0.074 Uiso 1 1 calc R H7B H 0.2753 0.7577 0.0635 0.074 Uiso 1 1 calc R H7C H 0.2637 0.7792 0.1354 0.074 Uiso 1 1 calc R F8 F 0.0103(3) 0.3229(5) 0.1756(2) 0.0693(12) Uani 1 1 d . C8 C 0.0865(4) 0.7968(7) -0.0088(3) 0.0454(16) Uani 1 1 d . H8A H 0.0845 0.8974 -0.0092 0.068 Uiso 1 1 calc R H8B H 0.0219 0.7605 -0.0253 0.068 Uiso 1 1 calc R H8C H 0.1242 0.7649 -0.0370 0.068 Uiso 1 1 calc R F9 F 0.0369(3) 0.3712(5) 0.2802(2) 0.0681(12) Uani 1 1 d . F10 F 0.1061(3) 0.0882(4) 0.20996(19) 0.0704(13) Uani 1 1 d . F11 F 0.1386(3) 0.1343(4) 0.31519(18) 0.0615(11) Uani 1 1 d . C11 C 0.2448(4) 0.3826(6) 0.3089(3) 0.0299(13) Uani 1 1 d . F12 F 0.2532(3) 0.0930(4) 0.2714(2) 0.0622(11) Uani 1 1 d . C12 C 0.1750(4) 0.3123(6) 0.2447(3) 0.0317(13) Uani 1 1 d . C13 C 0.0743(4) 0.3796(8) 0.2285(3) 0.0440(16) Uani 1 1 d . C14 C 0.1673(5) 0.1548(7) 0.2595(3) 0.0468(17) Uani 1 1 d . C15 C 0.4509(4) 0.4307(6) 0.3276(3) 0.0318(13) Uani 1 1 d . C16 C 0.4478(5) 0.3033(8) 0.2845(4) 0.068(2) Uani 1 1 d . H16A H 0.5102 0.2593 0.2968 0.101 Uiso 1 1 calc R H16B H 0.4305 0.3306 0.2382 0.101 Uiso 1 1 calc R H16C H 0.4005 0.2385 0.2911 0.101 Uiso 1 1 calc R C17 C 0.4806(5) 0.3880(9) 0.4000(3) 0.072(3) Uani 1 1 d . H17A H 0.5369 0.3293 0.4091 0.109 Uiso 1 1 calc R H17B H 0.4287 0.3374 0.4095 0.109 Uiso 1 1 calc R H17C H 0.4952 0.4701 0.4279 0.109 Uiso 1 1 calc R C18 C 0.5275(4) 0.5284(8) 0.3159(4) 0.073(2) Uani 1 1 d . H18A H 0.5875 0.4787 0.3239 0.109 Uiso 1 1 calc R H18B H 0.5361 0.6066 0.3461 0.109 Uiso 1 1 calc R H18C H 0.5071 0.5616 0.2704 0.109 Uiso 1 1 calc R C19 C 0.3156(4) 0.6701(6) 0.3485(3) 0.0308(13) Uani 1 1 d . C20 C 0.2098(4) 0.7218(7) 0.3228(3) 0.0516(18) Uani 1 1 d . H20A H 0.2028 0.8064 0.3458 0.077 Uiso 1 1 calc R H20B H 0.1674 0.6512 0.3311 0.077 Uiso 1 1 calc R H20C H 0.1935 0.7398 0.2754 0.077 Uiso 1 1 calc R C21 C 0.3374(5) 0.6384(7) 0.4225(3) 0.0500(17) Uani 1 1 d . H21A H 0.3227 0.7192 0.4453 0.075 Uiso 1 1 calc R H21B H 0.4046 0.6153 0.4408 0.075 Uiso 1 1 calc R H21C H 0.2986 0.5607 0.4286 0.075 Uiso 1 1 calc R C22 C 0.3802(5) 0.7895(6) 0.3377(3) 0.0486(17) Uani 1 1 d . H22A H 0.3715 0.8702 0.3628 0.073 Uiso 1 1 calc R H22B H 0.3630 0.8127 0.2908 0.073 Uiso 1 1 calc R H22C H 0.4467 0.7605 0.3526 0.073 Uiso 1 1 calc R H1 H 0.170(4) 0.470(6) -0.031(3) 0.022(14) Uiso 1 1 d . H11 H 0.284(4) 0.296(7) 0.336(3) 0.051(18) Uiso 1 1 d . H11' H 0.205(4) 0.421(7) 0.332(3) 0.054(19) Uiso 1 1 d . H1' H 0.226(5) 0.576(8) -0.002(4) 0.07(3) 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 Ge1 0.0213(3) 0.0332(3) 0.0221(3) -0.0004(3) 0.0055(2) -0.0018(3) P1 0.0213(7) 0.0407(10) 0.0281(8) -0.0023(6) 0.0036(6) -0.0008(6) F1 0.056(2) 0.055(3) 0.070(3) -0.003(2) 0.037(2) -0.019(2) C1 0.046(4) 0.049(5) 0.022(3) -0.003(3) 0.007(3) 0.007(3) O1 0.026(2) 0.043(2) 0.0208(19) -0.0033(17) 0.0044(15) 0.0044(17) P2 0.0228(7) 0.0299(8) 0.0226(7) 0.0000(6) 0.0071(5) -0.0001(6) F2 0.034(2) 0.068(3) 0.051(2) 0.0067(18) 0.0219(17) 0.0126(18) O2 0.038(2) 0.036(2) 0.026(2) -0.0017(17) 0.0121(17) -0.0079(18) C2 0.025(3) 0.042(4) 0.021(3) 0.000(2) 0.006(2) 0.001(3) F3 0.065(3) 0.069(3) 0.033(2) 0.0061(18) 0.0268(18) 0.012(2) N1 0.028(2) 0.031(3) 0.025(2) -0.0010(19) 0.0084(19) -0.004(2) C3 0.041(4) 0.040(4) 0.038(4) 0.004(3) 0.021(3) 0.008(3) F4 0.065(3) 0.066(3) 0.038(2) -0.0217(18) 0.0107(18) -0.010(2) C4 0.039(4) 0.044(4) 0.033(3) -0.002(3) 0.013(3) 0.000(3) F5 0.049(2) 0.034(2) 0.074(3) 0.0017(18) 0.0117(19) 0.0067(17) C5 0.031(3) 0.041(4) 0.032(3) -0.003(3) 0.003(3) 0.003(3) F6 0.046(2) 0.057(3) 0.058(2) -0.0094(18) 0.0230(18) -0.0133(18) C6 0.065(5) 0.053(5) 0.052(4) -0.004(3) 0.024(4) 0.019(4) F7 0.0288(18) 0.062(3) 0.057(2) 0.0062(19) 0.0124(16) 0.0052(17) C7 0.040(4) 0.046(4) 0.050(4) 0.014(3) -0.006(3) -0.003(3) F8 0.030(2) 0.100(4) 0.071(3) -0.014(2) 0.0042(19) -0.024(2) C8 0.038(4) 0.052(4) 0.042(4) 0.010(3) 0.005(3) 0.006(3) F9 0.043(2) 0.104(4) 0.071(3) 0.014(2) 0.037(2) 0.005(2) F10 0.092(3) 0.058(3) 0.055(3) -0.005(2) 0.014(2) -0.043(2) F11 0.074(3) 0.062(3) 0.053(2) 0.009(2) 0.027(2) -0.028(2) C11 0.029(3) 0.035(4) 0.029(3) -0.003(3) 0.013(3) -0.005(3) F12 0.072(3) 0.039(2) 0.077(3) 0.007(2) 0.024(2) -0.001(2) C12 0.029(3) 0.039(4) 0.029(3) -0.002(3) 0.010(2) -0.009(3) C13 0.037(4) 0.059(5) 0.035(4) -0.005(3) 0.011(3) -0.017(3) C14 0.063(5) 0.043(4) 0.034(4) -0.002(3) 0.013(3) -0.026(4) C15 0.028(3) 0.033(3) 0.034(3) 0.003(2) 0.006(2) 0.003(2) C16 0.043(4) 0.065(6) 0.087(6) -0.032(4) 0.008(4) 0.018(4) C17 0.055(5) 0.108(7) 0.057(5) 0.035(5) 0.020(4) 0.045(5) C18 0.023(4) 0.059(5) 0.128(7) 0.028(5) 0.009(4) -0.003(3) C19 0.033(3) 0.034(3) 0.026(3) -0.003(2) 0.008(2) 0.002(3) C20 0.041(4) 0.053(5) 0.055(4) -0.014(3) 0.006(3) 0.015(3) C21 0.072(5) 0.043(4) 0.035(4) -0.005(3) 0.017(3) 0.006(3) C22 0.061(4) 0.036(4) 0.050(4) -0.006(3) 0.019(3) -0.010(3) 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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ge Ge 0.1547 1.8001 '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' N N 0.0061 0.0033 '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 N1 Ge1 O1 112.98(17) N1 Ge1 O2 106.91(18) O1 Ge1 O2 99.15(17) N1 Ge1 P1 128.31(15) O1 Ge1 P1 95.91(11) O2 Ge1 P1 109.63(12) C1 P1 C5 102.9(3) C1 P1 Ge1 89.1(2) C5 P1 Ge1 103.99(18) C2 C1 P1 116.3(4) C2 O1 Ge1 117.3(3) N1 P2 C11 115.2(2) N1 P2 C19 107.2(2) C11 P2 C19 106.0(3) N1 P2 C15 111.8(2) C11 P2 C15 103.2(3) C19 P2 C15 113.3(2) C12 O2 Ge1 123.3(3) O1 C2 C4 108.0(4) O1 C2 C1 114.8(4) C4 C2 C1 109.3(5) O1 C2 C3 106.7(4) C4 C2 C3 110.0(5) C1 C2 C3 108.1(5) P2 N1 Ge1 121.9(3) F1 C3 F3 107.7(5) F1 C3 F2 106.0(5) F3 C3 F2 106.8(4) F1 C3 C2 110.6(5) F3 C3 C2 112.8(5) F2 C3 C2 112.5(5) F4 C4 F6 107.4(5) F4 C4 F5 106.8(5) F6 C4 F5 106.5(5) F4 C4 C2 113.3(5) F6 C4 C2 109.8(5) F5 C4 C2 112.7(5) C6 C5 C7 109.7(5) C6 C5 C8 110.4(5) C7 C5 C8 108.7(5) C6 C5 P1 106.1(4) C7 C5 P1 115.6(4) C8 C5 P1 106.3(4) C12 C11 P2 117.8(4) O2 C12 C13 108.0(4) O2 C12 C14 104.4(5) C13 C12 C14 109.4(5) O2 C12 C11 116.8(4) C13 C12 C11 109.8(5) C14 C12 C11 108.1(5) F8 C13 F7 106.5(5) F8 C13 F9 107.1(5) F7 C13 F9 106.7(5) F8 C13 C12 113.3(5) F7 C13 C12 110.5(5) F9 C13 C12 112.2(5) F10 C14 F12 108.0(6) F10 C14 F11 107.3(5) F12 C14 F11 106.3(5) F10 C14 C12 112.7(5) F12 C14 C12 110.5(5) F11 C14 C12 111.7(5) C17 C15 C16 109.3(6) C17 C15 C18 108.6(6) C16 C15 C18 107.3(6) C17 C15 P2 115.5(4) C16 C15 P2 107.0(4) C18 C15 P2 108.8(4) C21 C19 C22 110.2(5) C21 C19 C20 107.8(5) C22 C19 C20 107.2(5) C21 C19 P2 114.5(4) C22 C19 P2 108.7(4) C20 C19 P2 108.2(4) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance Ge1 N1 1.753(4) Ge1 O1 1.817(3) Ge1 O2 1.820(4) Ge1 P1 2.2988(15) P1 C1 1.871(6) P1 C5 1.878(6) F1 C3 1.332(7) C1 C2 1.533(8) O1 C2 1.394(6) P2 N1 1.576(4) P2 C11 1.851(6) P2 C19 1.853(6) P2 C15 1.880(6) F2 C3 1.347(6) O2 C12 1.394(6) C2 C4 1.533(8) C2 C3 1.534(7) F3 C3 1.333(6) F4 C4 1.333(6) C4 F6 1.334(6) C4 F5 1.335(7) C5 C6 1.519(8) C5 C7 1.531(8) C5 C8 1.545(8) F7 C13 1.339(7) F8 C13 1.329(7) F9 C13 1.341(6) F10 C14 1.310(7) F11 C14 1.356(7) C11 C12 1.571(8) F12 C14 1.330(8) C12 C13 1.535(8) C12 C14 1.544(8) C15 C17 1.500(8) C15 C16 1.504(8) C15 C18 1.520(8) C19 C21 1.512(7) C19 C22 1.532(8) C19 C20 1.545(8) 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 N1 Ge1 P1 C1 118.4(3) O1 Ge1 P1 C1 -7.2(3) O2 Ge1 P1 C1 -109.1(3) N1 Ge1 P1 C5 15.3(3) O1 Ge1 P1 C5 -110.3(2) O2 Ge1 P1 C5 147.7(2) C5 P1 C1 C2 124.5(5) Ge1 P1 C1 C2 20.4(5) N1 Ge1 O1 C2 -143.4(4) O2 Ge1 O1 C2 103.7(4) P1 Ge1 O1 C2 -7.3(4) N1 Ge1 O2 C12 38.2(4) O1 Ge1 O2 C12 155.7(4) P1 Ge1 O2 C12 -104.6(4) Ge1 O1 C2 C4 -99.1(4) Ge1 O1 C2 C1 23.0(6) Ge1 O1 C2 C3 142.7(4) P1 C1 C2 O1 -30.6(7) P1 C1 C2 C4 90.9(6) P1 C1 C2 C3 -149.5(5) C11 P2 N1 Ge1 -21.5(4) C19 P2 N1 Ge1 -139.3(3) C15 P2 N1 Ge1 95.9(3) O1 Ge1 N1 P2 -106.3(3) O2 Ge1 N1 P2 1.8(3) P1 Ge1 N1 P2 135.2(2) O1 C2 C3 F1 -56.4(6) C4 C2 C3 F1 -173.2(5) C1 C2 C3 F1 67.5(6) O1 C2 C3 F3 -177.1(4) C4 C2 C3 F3 66.0(6) C1 C2 C3 F3 -53.2(7) O1 C2 C3 F2 61.9(6) C4 C2 C3 F2 -54.9(6) C1 C2 C3 F2 -174.2(5) O1 C2 C4 F4 -172.6(4) C1 C2 C4 F4 61.9(6) C3 C2 C4 F4 -56.6(6) O1 C2 C4 F6 67.3(6) C1 C2 C4 F6 -58.1(6) C3 C2 C4 F6 -176.6(5) O1 C2 C4 F5 -51.2(6) C1 C2 C4 F5 -176.7(4) C3 C2 C4 F5 64.8(6) C1 P1 C5 C6 -178.0(4) Ge1 P1 C5 C6 -85.7(4) C1 P1 C5 C7 -56.2(5) Ge1 P1 C5 C7 36.1(5) C1 P1 C5 C8 64.4(4) Ge1 P1 C5 C8 156.7(3) N1 P2 C11 C12 11.9(6) C19 P2 C11 C12 130.3(4) C15 P2 C11 C12 -110.3(5) Ge1 O2 C12 C13 73.3(5) Ge1 O2 C12 C14 -170.4(4) Ge1 O2 C12 C11 -51.1(6) P2 C11 C12 O2 23.7(7) P2 C11 C12 C13 -99.7(5) P2 C11 C12 C14 140.9(4) O2 C12 C13 F8 53.3(7) C14 C12 C13 F8 -59.8(6) C11 C12 C13 F8 -178.3(5) O2 C12 C13 F7 -66.2(6) C14 C12 C13 F7 -179.3(5) C11 C12 C13 F7 62.2(6) O2 C12 C13 F9 174.8(5) C14 C12 C13 F9 61.7(7) C11 C12 C13 F9 -56.8(7) O2 C12 C14 F10 -58.6(7) C13 C12 C14 F10 56.8(7) C11 C12 C14 F10 176.4(5) O2 C12 C14 F12 62.4(6) C13 C12 C14 F12 177.8(5) C11 C12 C14 F12 -62.6(6) O2 C12 C14 F11 -179.5(5) C13 C12 C14 F11 -64.1(6) C11 C12 C14 F11 55.5(7) N1 P2 C15 C17 174.4(5) C11 P2 C15 C17 -61.2(6) C19 P2 C15 C17 53.0(6) N1 P2 C15 C16 -63.7(5) C11 P2 C15 C16 60.7(5) C19 P2 C15 C16 174.9(4) N1 P2 C15 C18 51.9(5) C11 P2 C15 C18 176.3(5) C19 P2 C15 C18 -69.5(5) N1 P2 C19 C21 -177.3(4) C11 P2 C19 C21 59.1(5) C15 P2 C19 C21 -53.4(5) N1 P2 C19 C22 -53.6(4) C11 P2 C19 C22 -177.2(4) C15 P2 C19 C22 70.3(4) N1 P2 C19 C20 62.5(4) C11 P2 C19 C20 -61.1(5) C15 P2 C19 C20 -173.6(4) _journal_paper_doi 10.1021/om060355c