# Supplementary Material (ESI) for New Journal of Chemistry # This journal is © The Royal Society of Chemistry and # The Centre National de la Recherche Scientifique, 2001 data_Copper(I)_complex _database_code_CSD 154547 _journal_coden_Cambridge 440 _publ_requested_journal 'New Journal of Chemistry' loop_ _publ_author_name 'Cesario, Michele' 'Charbonniere, Loic' 'Douce, Laurent' 'Ziessel, Raymond' _publ_contact_author_name 'Prof Raymond Ziessel' _publ_contact_author_address ; Prof Raymond Ziessel Laboratoire de Chimie d'Electronique et de Photonique Moleculaires ECPM, 1 rue Blaise Pascal Strasbourg F-67008 FRANCE ; _publ_contact_author_email 'ZIESSEL@CHIMIE.U-STRASBG.FR' _publ_section_title ; Phosphine-Oxyde Functionalised With Two Bipyridine Subunits: A Novel Ligand For the Engineering of Sterically Hindered Complexes ; _audit_creation_method SHELXL #_chemical_absolute_configuration unk??? _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety 'C30 H27 Cu N4 O P, B F4' _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C30 H27 B Cu F4 N4 O P' _chemical_formula_weight 640.88 _chemical_melting_point ? _chemical_compound_source ? 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' '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' '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' 'F' 'F' 0.0171 0.0103 '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' 'Cu' 'Cu' 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P-1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.430(3) _cell_length_b 14.002(5) _cell_length_c 15.206(6) _cell_angle_alpha 114.78(2) _cell_angle_beta 80.67(3) _cell_angle_gamma 98.49(3) _cell_volume 1411.7(9) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prism _exptl_crystal_colour 'brown' _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.508 _exptl_crystal_density_method ? _exptl_crystal_F_000 656 _exptl_absorpt_coefficient_mu 0.889 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71070 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'Nonius kappaCCD diffractometer' _diffrn_measurement_method 'phi scans ' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 18102 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0840 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.61 _diffrn_reflns_theta_max 26.73 _reflns_number_total 4975 _reflns_number_gt 3244 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Nonius Kappa-CCD Software' _computing_cell_refinement ; DENZO (Otwinovski & Minor,1997) COLLECT (Hooft,1998) ; _computing_data_reduction 'HKL package (Otwinovski & Minor,1997)' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics 'R3M (Riche,1983), ORTEP (Johson,1965)' _computing_publication_material 'SHELXL-93 (Sheldrick,1993)' _refine_special_details ; Refinement on F^2^ for ALL reflections except for 0 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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. The counterion BF4 is affected by disorder.Two positions are located on difference Fourier-syntheses with occupating factor of 0.8 and 0.2 respectively. The minor position is refined isotropically. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme 'calc w=1/[\s^2^(Fo^2^)+(0.1126P)^2^+0.2676P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4975 _refine_ls_number_parameters 398 _refine_ls_number_restraints 20 _refine_ls_R_factor_all 0.1109 _refine_ls_R_factor_gt 0.0683 _refine_ls_wR_factor_all 0.1953 _refine_ls_wR_factor_ref 0.1668 _refine_ls_goodness_of_fit_all 1.033 _refine_ls_goodness_of_fit_ref 1.112 _refine_ls_restrained_S_all 1.033 _refine_ls_restrained_S_obs 1.110 _refine_ls_shift/su_max -0.047 _refine_ls_shift/esd_mean 0.002 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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group Cu Cu 0.06058(8) 0.19474(4) 0.29745(4) 0.0605(3) Uani 1 d . . P P -0.1512(2) 0.46229(9) 0.35533(9) 0.0633(4) Uani 1 d . . O O -0.2182(5) 0.5474(3) 0.4488(3) 0.0806(10) Uani 1 d . . N1A N -0.1347(5) 0.2479(3) 0.4105(3) 0.0546(9) Uani 1 d . . C2A C -0.2749(6) 0.3028(3) 0.4176(3) 0.0600(11) Uani 1 d . . C3A C -0.4060(7) 0.3313(4) 0.4984(4) 0.0712(14) Uani 1 d . . H3A H -0.5019(7) 0.3692(4) 0.5024(4) 0.085 Uiso 1 calc R . C4A C -0.3897(8) 0.3019(4) 0.5719(4) 0.079(2) Uani 1 d . . H4A H -0.4784(8) 0.3172(4) 0.6255(4) 0.094 Uiso 1 calc R . C5A C -0.2442(8) 0.2503(4) 0.5668(4) 0.0720(14) Uani 1 d . . H5A H -0.2306(8) 0.2329(4) 0.6179(4) 0.086 Uiso 1 calc R . C6A C -0.1174(7) 0.2241(3) 0.4855(3) 0.0587(11) Uani 1 d . . C7A C -0.2779(6) 0.3339(4) 0.3351(4) 0.0642(12) Uani 1 d . . H7A1 H -0.4038(6) 0.3368(4) 0.3274(4) 0.077 Uiso 1 calc R . H7A2 H -0.2246(6) 0.2808(4) 0.2753(4) 0.077 Uiso 1 calc R . N1B N 0.1614(5) 0.1541(3) 0.3932(3) 0.0583(9) Uani 1 d . . C2B C 0.3114(7) 0.1031(4) 0.3780(4) 0.0646(12) Uani 1 d . . C3B C 0.3486(9) 0.0699(5) 0.4462(5) 0.087(2) Uani 1 d . . H3B H 0.4525(9) 0.0346(5) 0.4345(5) 0.105 Uiso 1 calc R . C4B C 0.2351(10) 0.0879(5) 0.5307(5) 0.093(2) Uani 1 d . . H4B H 0.2617(10) 0.0666(5) 0.5770(5) 0.112 Uiso 1 calc R . C5B C 0.0823(9) 0.1380(4) 0.5454(4) 0.080(2) Uani 1 d . . H5B H 0.0027(9) 0.1506(4) 0.6022(4) 0.096 Uiso 1 calc R . C6B C 0.0446(7) 0.1703(3) 0.4763(3) 0.0594(12) Uani 1 d . . C7B C 0.4334(7) 0.0862(4) 0.2858(4) 0.0780(15) Uani 1 d . . H7B1 H 0.3989(29) 0.0184(11) 0.2365(8) 0.094 Uiso 1 calc R . H7B2 H 0.5580(9) 0.0887(25) 0.2967(7) 0.094 Uiso 1 calc R . H7B3 H 0.4220(33) 0.1404(15) 0.2646(13) 0.094 Uiso 1 calc R . N1C N 0.1706(5) 0.2828(3) 0.2215(3) 0.0591(9) Uani 1 d . . C2C C 0.1846(6) 0.3887(4) 0.2525(4) 0.0648(12) Uani 1 d . . C3C C 0.2727(7) 0.4402(5) 0.1949(5) 0.082(2) Uani 1 d . . H6C H 0.2839(7) 0.5135(5) 0.2185(5) 0.098 Uiso 1 calc R . C4C C 0.3427(8) 0.3795(7) 0.1020(5) 0.098(2) Uani 1 d . . H4C H 0.4042(8) 0.4119(7) 0.0620(5) 0.117 Uiso 1 calc R . C5C C 0.3233(8) 0.2723(6) 0.0676(4) 0.090(2) Uani 1 d . . H5C H 0.3681(8) 0.2314(6) 0.0038(4) 0.108 Uiso 1 calc R . C6C C 0.2357(6) 0.2244(4) 0.1287(3) 0.0663(13) Uani 1 d . . C7C C 0.0897(7) 0.4485(4) 0.3521(4) 0.0659(13) Uani 1 d . . H7C1 H 0.1532(7) 0.5184(4) 0.3795(4) 0.079 Uiso 1 calc R . H7C2 H 0.1001(7) 0.4128(4) 0.3935(4) 0.079 Uiso 1 calc R . N1D N 0.0913(5) 0.0760(3) 0.1609(3) 0.0608(10) Uani 1 d . . C2D C 0.0511(7) -0.0275(4) 0.1375(4) 0.0721(14) Uani 1 d . . C3D C 0.1238(9) -0.1012(5) 0.0498(5) 0.095(2) Uani 1 d . . H3D H 0.0944(9) -0.1729(5) 0.0343(5) 0.114 Uiso 1 calc R . C4D C 0.2385(10) -0.0688(6) -0.0141(5) 0.107(2) Uani 1 d . . H4D H 0.2893(10) -0.1182(6) -0.0726(5) 0.129 Uiso 1 calc R . C5D C 0.2786(8) 0.0382(6) 0.0090(4) 0.089(2) Uani 1 d . . H5D H 0.3552(8) 0.0617(6) -0.0340(4) 0.107 Uiso 1 calc R . C6D C 0.2028(7) 0.1095(4) 0.0972(3) 0.0669(13) Uani 1 d . . C7D C -0.0739(8) -0.0600(4) 0.2105(5) 0.091(2) Uani 1 d . . H7D1 H -0.0084(16) -0.0975(25) 0.2335(20) 0.109 Uiso 1 calc R . H7D2 H -0.1767(26) -0.1049(24) 0.1800(9) 0.109 Uiso 1 calc R . H7D3 H -0.1166(41) 0.0018(5) 0.2643(14) 0.109 Uiso 1 calc R . C8 C -0.1705(7) 0.4854(4) 0.2494(4) 0.0694(13) Uani 1 d . . C9 C -0.1785(8) 0.5881(5) 0.2632(5) 0.091(2) Uani 1 d . . H9 H -0.1749(8) 0.6423(5) 0.3250(5) 0.109 Uiso 1 calc R . C10 C -0.1922(11) 0.6099(7) 0.1837(8) 0.128(3) Uani 1 d . . H10 H -0.2004(11) 0.6791(7) 0.1924(8) 0.153 Uiso 1 calc R . C11 C -0.1936(10) 0.5301(9) 0.0922(7) 0.118(3) Uani 1 d . . H11 H -0.1979(10) 0.5454(9) 0.0387(7) 0.142 Uiso 1 calc R . C12 C -0.1886(9) 0.4283(7) 0.0799(5) 0.106(2) Uani 1 d . . H12 H -0.1934(9) 0.3740(7) 0.0182(5) 0.127 Uiso 1 calc R . C13 C -0.1766(8) 0.4057(5) 0.1569(4) 0.085(2) Uani 1 d . . H13 H -0.1724(8) 0.3360(5) 0.1476(4) 0.102 Uiso 1 calc R . B B 0.3890(11) 0.7777(6) 0.1964(5) 0.087(2) Uani 1 d D . F1 F 0.4396(10) 0.8269(5) 0.1334(4) 0.131(2) Uani 0.80 d PD 1 F2 F 0.2151(8) 0.8011(7) 0.2379(5) 0.140(3) Uani 0.80 d PD 1 F3 F 0.5050(7) 0.8176(5) 0.2668(4) 0.121(2) Uani 0.80 d PD 1 F4 F 0.3928(12) 0.6730(5) 0.1466(7) 0.178(3) Uani 0.80 d PD 1 F1' F 0.3284(47) 0.7586(28) 0.1107(19) 0.174(12) Uiso 0.20 d PD 2 F2' F 0.5573(39) 0.8018(31) 0.1769(32) 0.207(14) Uiso 0.20 d PD 2 F3' F 0.3834(39) 0.6860(19) 0.2091(19) 0.125(9) Uiso 0.20 d PD 2 F4' F 0.2760(32) 0.8367(17) 0.2672(16) 0.094(7) Uiso 0.20 d PD 2 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 Cu 0.0620(4) 0.0630(4) 0.0567(4) 0.0251(3) -0.0014(3) 0.0091(3) P 0.0655(8) 0.0518(8) 0.0720(8) 0.0229(6) -0.0137(6) 0.0033(6) O 0.088(3) 0.066(2) 0.079(2) 0.018(2) -0.009(2) 0.016(2) N1A 0.053(2) 0.047(2) 0.061(2) 0.022(2) -0.005(2) -0.002(2) C2A 0.053(3) 0.051(3) 0.069(3) 0.021(2) -0.006(2) -0.007(2) C3A 0.052(3) 0.059(3) 0.085(4) 0.019(3) 0.007(2) -0.002(2) C4A 0.069(4) 0.074(4) 0.077(4) 0.027(3) 0.014(3) -0.007(3) C5A 0.079(4) 0.066(3) 0.065(3) 0.028(2) 0.001(3) -0.005(3) C6A 0.066(3) 0.048(3) 0.059(3) 0.023(2) -0.007(2) -0.010(2) C7A 0.050(3) 0.062(3) 0.078(3) 0.024(2) -0.013(2) 0.002(2) N1B 0.059(2) 0.046(2) 0.066(2) 0.018(2) -0.015(2) -0.001(2) C2B 0.061(3) 0.052(3) 0.077(3) 0.020(2) -0.022(3) -0.001(2) C3B 0.083(4) 0.084(4) 0.109(5) 0.043(3) -0.033(4) 0.011(3) C4B 0.109(5) 0.098(5) 0.096(4) 0.055(4) -0.027(4) 0.014(4) C5B 0.100(4) 0.069(3) 0.079(4) 0.041(3) -0.017(3) -0.009(3) C6B 0.069(3) 0.046(3) 0.060(3) 0.020(2) -0.014(2) -0.008(2) C7B 0.060(3) 0.077(3) 0.091(4) 0.023(3) -0.017(3) 0.011(3) N1C 0.046(2) 0.071(3) 0.061(2) 0.029(2) -0.004(2) 0.002(2) C2C 0.051(3) 0.071(4) 0.083(3) 0.042(3) -0.016(2) -0.008(2) C3C 0.058(3) 0.096(4) 0.109(5) 0.065(4) -0.012(3) -0.013(3) C4C 0.065(4) 0.145(7) 0.118(5) 0.093(5) 0.005(4) 0.007(4) C5C 0.071(4) 0.131(6) 0.080(4) 0.058(4) 0.003(3) 0.012(3) C6C 0.045(3) 0.094(4) 0.064(3) 0.038(3) -0.004(2) 0.005(2) C7C 0.065(3) 0.056(3) 0.079(3) 0.030(2) -0.021(3) -0.011(2) N1D 0.052(2) 0.069(3) 0.057(2) 0.017(2) -0.015(2) 0.009(2) C2D 0.060(3) 0.064(4) 0.084(4) 0.012(3) -0.032(3) 0.006(2) C3D 0.085(4) 0.079(4) 0.091(4) -0.006(3) -0.031(4) 0.021(3) C4D 0.090(5) 0.122(6) 0.074(4) -0.010(4) -0.019(4) 0.043(4) C5D 0.069(4) 0.121(5) 0.066(3) 0.020(3) -0.011(3) 0.029(3) C6D 0.053(3) 0.088(4) 0.054(3) 0.019(3) -0.012(2) 0.015(2) C7D 0.081(4) 0.064(3) 0.123(5) 0.032(3) -0.023(4) -0.004(3) C8 0.059(3) 0.070(3) 0.087(4) 0.039(3) -0.016(3) 0.000(2) C9 0.089(4) 0.077(4) 0.121(5) 0.057(4) -0.002(4) 0.013(3) C10 0.129(7) 0.122(7) 0.181(9) 0.111(7) 0.004(6) 0.028(5) C11 0.094(5) 0.184(9) 0.120(6) 0.105(6) -0.001(5) 0.022(5) C12 0.100(5) 0.136(6) 0.097(5) 0.058(4) -0.020(4) 0.014(4) C13 0.093(4) 0.085(4) 0.088(4) 0.043(3) -0.025(3) 0.002(3) B 0.090(5) 0.095(5) 0.085(5) 0.047(4) 0.007(4) 0.022(4) F1 0.169(5) 0.147(5) 0.094(3) 0.077(3) 0.043(3) 0.037(4) F2 0.069(4) 0.251(8) 0.133(5) 0.113(5) 0.012(4) 0.030(4) F3 0.095(3) 0.172(5) 0.106(4) 0.068(3) -0.025(3) -0.012(3) F4 0.244(9) 0.087(4) 0.204(8) 0.037(4) -0.085(7) 0.019(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 Cu N1A 2.013(4) . ? Cu N1C 2.028(4) . ? Cu N1B 2.045(4) . ? Cu N1D 2.048(4) . ? P O 1.487(4) . ? P C8 1.802(5) . ? P C7C 1.819(5) . ? P C7A 1.828(5) . ? N1A C6A 1.344(6) . ? N1A C2A 1.348(6) . ? C2A C3A 1.390(6) . ? C2A C7A 1.494(7) . ? C3A C4A 1.371(8) . ? C4A C5A 1.361(8) . ? C5A C6A 1.376(7) . ? C6A C6B 1.470(7) . ? N1B C2B 1.348(6) . ? N1B C6B 1.364(6) . ? C2B C3B 1.380(7) . ? C2B C7B 1.489(7) . ? C3B C4B 1.365(8) . ? C4B C5B 1.360(8) . ? C5B C6B 1.386(7) . ? N1C C2C 1.348(6) . ? N1C C6C 1.350(6) . ? C2C C3C 1.385(7) . ? C2C C7C 1.502(7) . ? C3C C4C 1.369(8) . ? C4C C5C 1.360(9) . ? C5C C6C 1.390(8) . ? C6C C6D 1.468(7) . ? N1D C2D 1.338(6) . ? N1D C6D 1.359(6) . ? C2D C3D 1.383(7) . ? C2D C7D 1.505(8) . ? C3D C4D 1.364(10) . ? C4D C5D 1.385(10) . ? C5D C6D 1.382(7) . ? C8 C9 1.372(8) . ? C8 C13 1.384(8) . ? C9 C10 1.387(10) . ? C10 C11 1.372(11) . ? C11 C12 1.363(11) . ? C12 C13 1.354(9) . ? B F2' 1.27(3) . ? B F4' 1.31(2) . ? B F4 1.341(9) . ? B F1' 1.35(2) . ? B F3 1.363(9) . ? B F2 1.365(9) . ? B F3' 1.37(2) . ? B F1 1.375(8) . ? 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 N1A Cu N1C 121.10(15) . . ? N1A Cu N1B 81.5(2) . . ? N1C Cu N1B 132.8(2) . . ? N1A Cu N1D 139.2(2) . . ? N1C Cu N1D 81.0(2) . . ? N1B Cu N1D 109.30(15) . . ? O P C8 113.6(2) . . ? O P C7C 110.9(2) . . ? C8 P C7C 106.3(2) . . ? O P C7A 112.6(2) . . ? C8 P C7A 105.2(2) . . ? C7C P C7A 107.8(2) . . ? C6A N1A C2A 118.9(4) . . ? C6A N1A Cu 113.8(3) . . ? C2A N1A Cu 127.3(3) . . ? N1A C2A C3A 121.8(4) . . ? N1A C2A C7A 116.2(4) . . ? C3A C2A C7A 122.0(4) . . ? C4A C3A C2A 118.1(5) . . ? C5A C4A C3A 120.2(5) . . ? C4A C5A C6A 119.6(5) . . ? N1A C6A C5A 121.3(5) . . ? N1A C6A C6B 116.4(4) . . ? C5A C6A C6B 122.2(4) . . ? C2A C7A P 111.9(3) . . ? C2B N1B C6B 119.0(4) . . ? C2B N1B Cu 127.9(3) . . ? C6B N1B Cu 112.6(3) . . ? N1B C2B C3B 120.6(5) . . ? N1B C2B C7B 116.9(4) . . ? C3B C2B C7B 122.4(5) . . ? C4B C3B C2B 121.0(5) . . ? C5B C4B C3B 118.4(5) . . ? C4B C5B C6B 120.4(5) . . ? N1B C6B C5B 120.6(5) . . ? N1B C6B C6A 115.1(4) . . ? C5B C6B C6A 124.3(5) . . ? C2C N1C C6C 118.5(4) . . ? C2C N1C Cu 128.1(3) . . ? C6C N1C Cu 113.4(3) . . ? N1C C2C C3C 122.6(5) . . ? N1C C2C C7C 116.0(4) . . ? C3C C2C C7C 121.3(5) . . ? C4C C3C C2C 117.8(6) . . ? C5C C4C C3C 120.7(5) . . ? C4C C5C C6C 119.4(6) . . ? N1C C6C C5C 120.9(5) . . ? N1C C6C C6D 115.7(4) . . ? C5C C6C C6D 123.3(5) . . ? C2C C7C P 115.0(3) . . ? C2D N1D C6D 119.8(4) . . ? C2D N1D Cu 126.6(4) . . ? C6D N1D Cu 111.6(3) . . ? N1D C2D C3D 120.8(6) . . ? N1D C2D C7D 117.5(5) . . ? C3D C2D C7D 121.7(6) . . ? C4D C3D C2D 120.0(6) . . ? C3D C4D C5D 119.4(6) . . ? C6D C5D C4D 118.8(6) . . ? N1D C6D C5D 121.1(6) . . ? N1D C6D C6C 115.7(4) . . ? C5D C6D C6C 123.3(5) . . ? C9 C8 C13 119.7(5) . . ? C9 C8 P 117.0(5) . . ? C13 C8 P 123.3(4) . . ? C8 C9 C10 119.1(7) . . ? C11 C10 C9 120.3(7) . . ? C12 C11 C10 119.8(7) . . ? C13 C12 C11 120.5(7) . . ? C12 C13 C8 120.5(6) . . ? F2' B F4' 126.8(23) . . ? F2' B F1' 99.6(24) . . ? F4' B F1' 108.2(19) . . ? F4 B F3 112.1(7) . . ? F4 B F2 109.9(8) . . ? F3 B F2 109.5(7) . . ? F2' B F3' 105.0(24) . . ? F4' B F3' 105.9(17) . . ? F1' B F3' 110.9(20) . . ? F4 B F1 109.5(7) . . ? F3 B F1 108.3(7) . . ? F2 B F1 107.5(6) . . ? _refine_diff_density_max 0.597 _refine_diff_density_min -0.452 _refine_diff_density_rms 0.087