# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full Chem.Commun. _journal_coden_cambridge 0182 _publ_section_title ; Neutral copper-phosphido-borane complexes: Synthesis, characterization, and catalytic activity in Csp-P bond formation ; _publ_section_abstract ; Copper-phosphido-borane complexes were synthesized and isolated for the first time. Their structure was experimentally and computationally investigated. They were shown to display catalytic activity in Csp-P bond formation. ; _publ_contact_author_name 'Gaumont, Annie-Claude' _publ_contact_author_address ; Laboratoire de Chimie Mol\'eculaire et Thio-organique, UMR CNRS 6507, FR CNRS 3038 INC3M ENSICAEN - Universit\'e de Caen 14050 Caen France ; _publ_contact_author_phone '332 31 45 28 73' _publ_contact_author_fax '332 31 45 28 65' _publ_contact_author_email annie-claude.gaumont@ensicaen.fr loop_ _publ_author_address ; Laboratoire de Chimie Mol\'eculaire et Thio-organique, UMR CNRS 6507, FR CNRS 3038 INC3M ENSICAEN - Universit\'e de Caen 14050 Caen France ; ; Laboratoire de Chimie Mol\'eculaire et Thio-organique, UMR CNRS 6507, FR CNRS 3038 INC3M ENSICAEN - Universit\'e de Caen 14050 Caen France ; loop_ _publ_author_name A.-C.Gaumont I.Abdellah E.Bernoud J.-F.Lohier C.Alayrac ; L.Toupet ; C.Lepetit data_3b _database_code_depnum_ccdc_archive 'CCDC 857695' #TrackingRef 'CIFChemComm-3b.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; Et2PHCuIphen ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C16 H19 Cu I N2 P' _chemical_formula_sum 'C16 H19 Cu I N2 P' _chemical_formula_weight 460.74 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' 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' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P2(1)/n ' _symmetry_space_group_name_Hall '-P 2yn' 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' _cell_length_a 7.630(4) _cell_length_b 15.462(9) _cell_length_c 14.750(8) _cell_angle_alpha 90.00 _cell_angle_beta 91.94(4) _cell_angle_gamma 90.00 _cell_volume 1739.2(16) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 9814 _cell_measurement_theta_min 2.64 _cell_measurement_theta_max 32.16 _exptl_crystal_description block _exptl_crystal_colour orange _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.760 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 904 _exptl_absorpt_coefficient_mu 3.118 _exptl_absorpt_correction_type numerical _exptl_absorpt_correction_T_min 0.2809 _exptl_absorpt_correction_T_max 0.5367 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 44076 _diffrn_reflns_av_R_equivalents 0.0284 _diffrn_reflns_av_sigmaI/netI 0.0170 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 2.76 _diffrn_reflns_theta_max 32.23 _reflns_number_total 6148 _reflns_number_gt 5254 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^ > 2sigma(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^)+(0.0205P)^2^+1.3236P] 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 refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6148 _refine_ls_number_parameters 266 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0320 _refine_ls_R_factor_gt 0.0224 _refine_ls_wR_factor_ref 0.0568 _refine_ls_wR_factor_gt 0.0512 _refine_ls_goodness_of_fit_ref 1.101 _refine_ls_restrained_S_all 1.101 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 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 I1 I 0.616306(15) 0.199588(7) 0.053051(8) 0.02756(4) Uani 1 1 d . . . Cu1 Cu 0.91057(3) 0.290588(13) 0.033274(15) 0.02460(5) Uani 1 1 d . . . P1 P 1.07729(6) 0.18916(3) -0.02070(3) 0.02402(8) Uani 1 1 d . . . N1 N 0.81784(19) 0.40881(9) -0.01677(10) 0.0228(3) Uani 1 1 d . . . N2 N 0.9293(2) 0.36337(10) 0.15188(10) 0.0259(3) Uani 1 1 d . . . C2 C 0.6876(3) 0.51144(12) -0.12108(13) 0.0305(4) Uani 1 1 d . . . C7 C 0.8446(2) 0.50320(12) 0.21268(12) 0.0282(3) Uani 1 1 d . . . C5 C 0.7074(3) 0.60825(12) 0.11103(14) 0.0326(4) Uani 1 1 d . . . C6 C 0.7656(3) 0.58631(12) 0.19529(14) 0.0338(4) Uani 1 1 d . . . C10 C 0.9875(3) 0.34157(13) 0.23489(13) 0.0325(4) Uani 1 1 d . . . C8 C 0.9090(3) 0.47749(14) 0.29929(13) 0.0349(4) Uani 1 1 d . . . C9 C 0.9805(3) 0.39698(15) 0.31017(14) 0.0372(4) Uani 1 1 d . . . C4 C 0.7242(2) 0.55008(11) 0.03568(12) 0.0255(3) Uani 1 1 d . . . C11 C 0.8594(2) 0.44382(11) 0.14077(11) 0.0235(3) Uani 1 1 d . . . C12 C 0.7989(2) 0.46803(10) 0.05067(11) 0.0223(3) Uani 1 1 d . . . C15 C 1.1119(3) 0.09502(13) 0.05383(14) 0.0346(4) Uani 1 1 d . . . C1 C 0.7627(3) 0.43080(11) -0.09995(12) 0.0276(3) Uani 1 1 d . . . C13 C 0.9908(3) 0.13749(12) -0.12505(13) 0.0299(4) Uani 1 1 d . . . C14 C 0.9768(5) 0.19960(16) -0.20447(16) 0.0490(6) Uani 1 1 d . . . C16 C 1.1640(3) 0.11795(15) 0.15103(15) 0.0383(4) Uani 1 1 d . . . C3 C 0.6683(3) 0.57131(12) -0.05338(14) 0.0300(4) Uani 1 1 d . . . H8 H 1.040(3) 0.2860(14) 0.2420(16) 0.030(6) Uiso 1 1 d . . . H6 H 0.902(3) 0.5160(16) 0.3484(17) 0.039(6) Uiso 1 1 d . . . H5 H 0.756(3) 0.6233(16) 0.2455(17) 0.037(6) Uiso 1 1 d . . . H9 H 0.878(3) 0.1152(16) -0.1117(17) 0.043(7) Uiso 1 1 d . . . H2 H 0.650(3) 0.5220(16) -0.1806(17) 0.038(6) Uiso 1 1 d . . . H7 H 1.017(3) 0.3789(16) 0.3664(18) 0.040(7) Uiso 1 1 d . . . H10 H 1.067(4) 0.0892(18) -0.1396(18) 0.050(7) Uiso 1 1 d . . . H11 H 0.921(4) 0.1755(19) -0.257(2) 0.055(8) Uiso 1 1 d . . . H1 H 0.779(3) 0.3894(15) -0.1457(16) 0.036(6) Uiso 1 1 d . . . H12 H 1.092(5) 0.224(2) -0.219(2) 0.075(11) Uiso 1 1 d . . . H4 H 0.648(4) 0.6642(18) 0.0992(18) 0.047(7) Uiso 1 1 d . . . H3 H 0.614(3) 0.6260(16) -0.0632(17) 0.039(6) Uiso 1 1 d . . . H15 H 1.002(4) 0.0670(17) 0.0505(17) 0.042(7) Uiso 1 1 d . . . H19 H 1.236(3) 0.2041(14) -0.0440(17) 0.038(7) Uiso 1 1 d . . . H14 H 1.200(4) 0.0583(17) 0.0278(18) 0.047(7) Uiso 1 1 d . . . H16 H 1.266(4) 0.157(2) 0.155(2) 0.061(9) Uiso 1 1 d . . . H17 H 1.066(4) 0.1449(18) 0.1798(18) 0.047(7) Uiso 1 1 d . . . H18 H 1.187(4) 0.067(2) 0.184(2) 0.060(8) Uiso 1 1 d . . . H13 H 0.902(4) 0.247(2) -0.190(2) 0.065(9) 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 I1 0.02424(6) 0.03043(6) 0.02794(6) 0.00082(4) 0.00005(4) -0.00484(4) Cu1 0.02687(10) 0.02089(9) 0.02586(10) -0.00070(7) -0.00180(8) -0.00008(7) P1 0.02209(19) 0.02247(18) 0.0274(2) 0.00179(15) -0.00002(15) -0.00077(15) N1 0.0235(6) 0.0213(6) 0.0237(6) 0.0002(5) 0.0009(5) -0.0031(5) N2 0.0261(7) 0.0257(7) 0.0258(7) 0.0000(5) -0.0027(5) -0.0042(5) C2 0.0348(9) 0.0280(8) 0.0286(8) 0.0061(7) 0.0003(7) 0.0000(7) C7 0.0284(8) 0.0295(8) 0.0270(8) -0.0046(6) 0.0047(7) -0.0096(7) C5 0.0348(10) 0.0216(8) 0.0419(10) -0.0037(7) 0.0096(8) -0.0028(7) C6 0.0373(10) 0.0275(8) 0.0373(10) -0.0097(7) 0.0099(8) -0.0078(7) C10 0.0344(10) 0.0336(9) 0.0291(9) 0.0018(7) -0.0065(7) -0.0027(7) C8 0.0366(10) 0.0420(10) 0.0261(8) -0.0076(8) 0.0023(7) -0.0108(8) C9 0.0384(10) 0.0478(11) 0.0250(8) -0.0002(8) -0.0043(7) -0.0090(9) C4 0.0251(8) 0.0198(7) 0.0318(8) 0.0003(6) 0.0054(6) -0.0047(6) C11 0.0218(7) 0.0234(7) 0.0254(7) -0.0006(6) 0.0019(6) -0.0071(6) C12 0.0223(7) 0.0204(7) 0.0243(7) 0.0001(5) 0.0032(6) -0.0058(5) C15 0.0417(11) 0.0250(8) 0.0368(10) 0.0044(7) -0.0025(8) 0.0035(8) C1 0.0336(9) 0.0247(8) 0.0243(8) 0.0004(6) 0.0001(7) -0.0002(7) C13 0.0331(9) 0.0255(8) 0.0313(9) -0.0020(7) 0.0024(7) -0.0009(7) C14 0.0786(19) 0.0368(11) 0.0307(10) 0.0013(9) -0.0107(11) -0.0100(12) C16 0.0440(12) 0.0388(11) 0.0321(10) 0.0079(8) 0.0021(9) 0.0012(9) C3 0.0310(9) 0.0225(7) 0.0369(9) 0.0056(7) 0.0040(7) -0.0008(7) _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 I1 Cu1 2.6741(11) . ? Cu1 N2 2.0810(17) . ? Cu1 N1 2.0860(17) . ? Cu1 P1 2.1864(10) . ? P1 C13 1.837(2) . ? P1 C15 1.838(2) . ? P1 H19 1.29(3) . ? N1 C1 1.328(2) . ? N1 C12 1.363(2) . ? N2 C10 1.332(2) . ? N2 C11 1.361(2) . ? C2 C3 1.373(3) . ? C2 C1 1.403(3) . ? C2 H2 0.93(2) . ? C7 C8 1.410(3) . ? C7 C11 1.410(2) . ? C7 C6 1.439(3) . ? C5 C6 1.349(3) . ? C5 C4 1.439(3) . ? C5 H4 0.99(3) . ? C6 H5 0.94(2) . ? C10 C9 1.405(3) . ? C10 H8 0.95(2) . ? C8 C9 1.366(3) . ? C8 H6 0.94(2) . ? C9 H7 0.91(3) . ? C4 C12 1.405(2) . ? C4 C3 1.406(3) . ? C11 C12 1.442(2) . ? C15 C16 1.517(3) . ? C15 H15 0.95(3) . ? C15 H14 0.97(3) . ? C1 H1 0.94(2) . ? C13 C14 1.516(3) . ? C13 H9 0.96(3) . ? C13 H10 0.97(3) . ? C14 H11 0.95(3) . ? C14 H12 0.99(4) . ? C14 H13 0.96(3) . ? C16 H16 0.99(3) . ? C16 H17 0.97(3) . ? C16 H18 0.93(3) . ? C3 H3 0.95(2) . ? 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 N2 Cu1 N1 80.59(7) . . ? N2 Cu1 P1 132.05(5) . . ? N1 Cu1 P1 133.97(5) . . ? N2 Cu1 I1 103.12(6) . . ? N1 Cu1 I1 102.92(5) . . ? P1 Cu1 I1 99.40(4) . . ? C13 P1 C15 101.37(10) . . ? C13 P1 Cu1 114.84(7) . . ? C15 P1 Cu1 115.09(8) . . ? C13 P1 H19 99.7(11) . . ? C15 P1 H19 100.6(10) . . ? Cu1 P1 H19 122.0(10) . . ? C1 N1 C12 117.65(15) . . ? C1 N1 Cu1 130.12(12) . . ? C12 N1 Cu1 111.93(11) . . ? C10 N2 C11 117.34(16) . . ? C10 N2 Cu1 130.35(14) . . ? C11 N2 Cu1 112.18(12) . . ? C3 C2 C1 119.37(18) . . ? C3 C2 H2 122.2(15) . . ? C1 C2 H2 118.4(15) . . ? C8 C7 C11 117.62(18) . . ? C8 C7 C6 122.98(17) . . ? C11 C7 C6 119.40(17) . . ? C6 C5 C4 121.29(18) . . ? C6 C5 H4 121.1(16) . . ? C4 C5 H4 117.6(16) . . ? C5 C6 C7 120.78(17) . . ? C5 C6 H5 122.7(15) . . ? C7 C6 H5 116.5(15) . . ? N2 C10 C9 123.49(19) . . ? N2 C10 H8 117.1(15) . . ? C9 C10 H8 119.4(15) . . ? C9 C8 C7 119.25(18) . . ? C9 C8 H6 121.3(15) . . ? C7 C8 H6 119.5(15) . . ? C8 C9 C10 119.24(19) . . ? C8 C9 H7 119.8(16) . . ? C10 C9 H7 120.9(16) . . ? C12 C4 C3 117.79(16) . . ? C12 C4 C5 119.29(17) . . ? C3 C4 C5 122.92(17) . . ? N2 C11 C7 123.04(16) . . ? N2 C11 C12 117.41(15) . . ? C7 C11 C12 119.55(16) . . ? N1 C12 C4 122.96(16) . . ? N1 C12 C11 117.36(15) . . ? C4 C12 C11 119.67(15) . . ? C16 C15 P1 114.09(15) . . ? C16 C15 H15 111.1(15) . . ? P1 C15 H15 102.8(15) . . ? C16 C15 H14 110.4(16) . . ? P1 C15 H14 108.3(16) . . ? H15 C15 H14 110(2) . . ? N1 C1 C2 123.17(17) . . ? N1 C1 H1 116.4(15) . . ? C2 C1 H1 120.5(15) . . ? C14 C13 P1 112.71(15) . . ? C14 C13 H9 110.3(15) . . ? P1 C13 H9 106.6(15) . . ? C14 C13 H10 110.0(16) . . ? P1 C13 H10 108.5(16) . . ? H9 C13 H10 109(2) . . ? C13 C14 H11 113.9(18) . . ? C13 C14 H12 112(2) . . ? H11 C14 H12 110(3) . . ? C13 C14 H13 109.5(18) . . ? H11 C14 H13 104(3) . . ? H12 C14 H13 107(3) . . ? C15 C16 H16 112.5(18) . . ? C15 C16 H17 109.6(16) . . ? H16 C16 H17 109(2) . . ? C15 C16 H18 109.1(18) . . ? H16 C16 H18 111(3) . . ? H17 C16 H18 106(2) . . ? C2 C3 C4 119.05(17) . . ? C2 C3 H3 123.0(15) . . ? C4 C3 H3 117.9(15) . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 32.23 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.759 _refine_diff_density_min -0.547 _refine_diff_density_rms 0.095 _publ_section_abstract ; Copper-phosphido-borane complexes were synthesized and isolated for the first time. Their structure was experimentally and computationally investigated. They were shown to display catalytic activity in Csp-P bond formation. ; # Attachment 'CIFChemComm-4a.cif' data_4a _database_code_depnum_ccdc_archive 'CCDC 857696' #TrackingRef 'CIFChemComm-4a.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; Ph2PHCuPPh2BH3phen ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C36 H32 B Cu N2 P2' _chemical_formula_sum 'C36 H32 B Cu N2 P2' _chemical_formula_weight 628.93 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' N N 0.0061 0.0033 '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' 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 ' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.7656(14) _cell_length_b 11.5098(17) _cell_length_c 16.082(3) _cell_angle_alpha 98.116(3) _cell_angle_beta 99.785(3) _cell_angle_gamma 112.221(4) _cell_volume 1606.7(4) _cell_formula_units_Z 2 _cell_measurement_temperature 291(2) _cell_measurement_reflns_used 9936 _cell_measurement_theta_min 2.63 _cell_measurement_theta_max 30.67 _exptl_crystal_description block _exptl_crystal_colour orange _exptl_crystal_size_max 0.17 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.09 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.300 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 652 _exptl_absorpt_coefficient_mu 0.807 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 291(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 30590 _diffrn_reflns_av_R_equivalents 0.0179 _diffrn_reflns_av_sigmaI/netI 0.0187 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 3.06 _diffrn_reflns_theta_max 29.14 _reflns_number_total 8546 _reflns_number_gt 6931 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^ > 2sigma(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^)+(0.0554P)^2^+0.2706P] 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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 8546 _refine_ls_number_parameters 384 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0448 _refine_ls_R_factor_gt 0.0330 _refine_ls_wR_factor_ref 0.0977 _refine_ls_wR_factor_gt 0.0900 _refine_ls_goodness_of_fit_ref 1.023 _refine_ls_restrained_S_all 1.023 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 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 Cu1 Cu 0.84730(2) 0.632391(16) 0.707331(12) 0.04168(7) Uani 1 1 d . . . P1 P 0.64362(5) 0.51971(4) 0.75392(3) 0.04319(10) Uani 1 1 d . . . P2 P 1.06931(5) 0.61059(4) 0.74349(3) 0.04174(9) Uani 1 1 d . . . N2 N 0.79440(15) 0.67985(12) 0.59016(8) 0.0443(3) Uani 1 1 d . . . N1 N 0.87052(15) 0.82528(12) 0.75084(9) 0.0448(3) Uani 1 1 d . . . C13 C 0.68077(18) 0.57961(15) 0.87016(10) 0.0443(3) Uani 1 1 d . . . C18 C 0.8160(2) 0.59055(18) 0.92215(12) 0.0547(4) Uani 1 1 d . . . H13 H 0.8822 0.5645 0.8975 0.066 Uiso 1 1 calc R . . C17 C 0.8526(2) 0.6400(2) 1.01039(12) 0.0645(5) Uani 1 1 d . . . H12 H 0.9433 0.6469 1.0448 0.077 Uiso 1 1 calc R . . C16 C 0.7562(3) 0.6790(2) 1.04743(13) 0.0725(6) Uani 1 1 d . . . H11 H 0.7813 0.7119 1.1069 0.087 Uiso 1 1 calc R . . C15 C 0.6234(3) 0.6694(2) 0.99698(15) 0.0766(6) Uani 1 1 d . . . H10 H 0.5583 0.6963 1.0222 0.092 Uiso 1 1 calc R . . C14 C 0.5848(2) 0.6199(2) 0.90827(13) 0.0607(4) Uani 1 1 d . . . H9 H 0.4941 0.6138 0.8743 0.073 Uiso 1 1 calc R . . C19 C 0.55901(19) 0.34460(15) 0.74072(10) 0.0457(3) Uani 1 1 d . . . C20 C 0.6137(2) 0.2696(2) 0.69474(17) 0.0725(6) Uani 1 1 d . . . H14 H 0.6963 0.3079 0.6715 0.087 Uiso 1 1 calc R . . C21 C 0.5456(3) 0.1358(2) 0.6828(2) 0.0921(8) Uani 1 1 d . . . H15 H 0.5812 0.0852 0.6501 0.111 Uiso 1 1 calc R . . C22 C 0.4267(3) 0.0785(2) 0.71875(17) 0.0780(6) Uani 1 1 d . . . H16 H 0.3832 -0.0105 0.7117 0.094 Uiso 1 1 calc R . . C23 C 0.3718(3) 0.1531(2) 0.76535(14) 0.0725(6) Uani 1 1 d . . . H17 H 0.2907 0.1146 0.7896 0.087 Uiso 1 1 calc R . . C24 C 0.4373(2) 0.28473(18) 0.77602(12) 0.0613(5) Uani 1 1 d . . . H18 H 0.3994 0.3346 0.8075 0.074 Uiso 1 1 calc R . . C11 C 0.82169(17) 0.80628(15) 0.59802(10) 0.0427(3) Uani 1 1 d . . . C7 C 0.8094(2) 0.86241(19) 0.52642(13) 0.0570(4) Uani 1 1 d . . . C6 C 0.8375(3) 0.9965(2) 0.54151(17) 0.0750(6) Uani 1 1 d . . . H5 H 0.8303 1.0343 0.4945 0.090 Uiso 1 1 calc R . . C5 C 0.8736(3) 1.0677(2) 0.62113(18) 0.0750(6) Uani 1 1 d . . . H4 H 0.8918 1.1543 0.6285 0.090 Uiso 1 1 calc R . . C4 C 0.8849(2) 1.01411(16) 0.69585(14) 0.0578(4) Uani 1 1 d . . . C3 C 0.9156(2) 1.08297(18) 0.78108(16) 0.0726(6) Uani 1 1 d . . . H3 H 0.9325 1.1694 0.7919 0.087 Uiso 1 1 calc R . . C2 C 0.9207(3) 1.0234(2) 0.84737(15) 0.0734(6) Uani 1 1 d . . . H2 H 0.9384 1.0679 0.9038 0.088 Uiso 1 1 calc R . . C1 C 0.8992(2) 0.89446(18) 0.83062(12) 0.0586(4) Uani 1 1 d . . . H1 H 0.9051 0.8552 0.8770 0.070 Uiso 1 1 calc R . . C12 C 0.86153(16) 0.88345(14) 0.68416(11) 0.0424(3) Uani 1 1 d . . . C8 C 0.7707(3) 0.7833(2) 0.44443(14) 0.0735(6) Uani 1 1 d . . . H6 H 0.7635 0.8172 0.3955 0.088 Uiso 1 1 calc R . . C9 C 0.7436(3) 0.6572(2) 0.43575(13) 0.0718(6) Uani 1 1 d . . . H7 H 0.7184 0.6042 0.3812 0.086 Uiso 1 1 calc R . . C10 C 0.7541(2) 0.60797(19) 0.51029(12) 0.0593(4) Uani 1 1 d . . . H8 H 0.7317 0.5207 0.5036 0.071 Uiso 1 1 calc R . . C25 C 1.17438(18) 0.71356(16) 0.85158(11) 0.0492(4) Uani 1 1 d . . . C26 C 1.2167(2) 0.84609(18) 0.86743(15) 0.0643(5) Uani 1 1 d . . . H19 H 1.1980 0.8836 0.8217 0.077 Uiso 1 1 calc R . . C27 C 1.2861(3) 0.9231(2) 0.95025(19) 0.0855(7) Uani 1 1 d . . . H20 H 1.3141 1.0115 0.9595 0.103 Uiso 1 1 calc R . . C28 C 1.3137(3) 0.8688(3) 1.01882(17) 0.0909(8) Uani 1 1 d . . . H21 H 1.3594 0.9203 1.0744 0.109 Uiso 1 1 calc R . . C29 C 1.2737(3) 0.7391(3) 1.00470(15) 0.0803(7) Uani 1 1 d . . . H22 H 1.2920 0.7025 1.0510 0.096 Uiso 1 1 calc R . . C30 C 1.2057(2) 0.6613(2) 0.92165(13) 0.0630(5) Uani 1 1 d . . . H23 H 1.1808 0.5734 0.9129 0.076 Uiso 1 1 calc R . . C31 C 1.20359(18) 0.67764(15) 0.67727(11) 0.0463(3) Uani 1 1 d . . . C36 C 1.1512(2) 0.6744(2) 0.59152(14) 0.0643(5) Uani 1 1 d . . . H28 H 1.0466 0.6418 0.5682 0.077 Uiso 1 1 calc R . . C35 C 1.2499(3) 0.7185(2) 0.53839(16) 0.0777(6) Uani 1 1 d . . . H27 H 1.2112 0.7155 0.4808 0.093 Uiso 1 1 calc R . . C34 C 1.4035(3) 0.7659(2) 0.57163(19) 0.0807(7) Uani 1 1 d . . . H26 H 1.4705 0.7955 0.5369 0.097 Uiso 1 1 calc R . . C33 C 1.4577(3) 0.7693(3) 0.6563(2) 0.0857(7) Uani 1 1 d . . . H25 H 1.5625 0.8011 0.6789 0.103 Uiso 1 1 calc R . . C32 C 1.3604(2) 0.7266(2) 0.70932(16) 0.0682(5) Uani 1 1 d . . . H24 H 1.4004 0.7308 0.7670 0.082 Uiso 1 1 calc R . . B1 B 1.0616(3) 0.43881(19) 0.74269(15) 0.0572(5) Uani 1 1 d . . . H1A H 1.1630 0.4448 0.7625 0.086 Uiso 1 1 calc R . . H1B H 1.0180 0.3866 0.6848 0.086 Uiso 1 1 calc R . . H1C H 1.0000 0.4004 0.7803 0.086 Uiso 1 1 calc R . . H29 H 0.511(2) 0.5335(19) 0.7299(13) 0.063(6) 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 Cu1 0.04533(12) 0.03499(10) 0.04592(11) 0.01174(7) 0.01263(8) 0.01628(8) P1 0.0419(2) 0.0405(2) 0.0463(2) 0.01354(16) 0.01106(16) 0.01462(17) P2 0.0412(2) 0.03294(18) 0.0521(2) 0.01400(16) 0.01302(17) 0.01417(15) N2 0.0457(7) 0.0411(7) 0.0460(7) 0.0075(5) 0.0096(5) 0.0194(6) N1 0.0452(7) 0.0360(6) 0.0505(7) 0.0048(5) 0.0121(6) 0.0155(5) C13 0.0454(8) 0.0375(7) 0.0474(8) 0.0125(6) 0.0143(7) 0.0121(6) C18 0.0484(9) 0.0613(10) 0.0537(9) 0.0174(8) 0.0144(8) 0.0194(8) C17 0.0555(11) 0.0720(13) 0.0525(10) 0.0163(9) 0.0075(8) 0.0135(9) C16 0.0692(13) 0.0746(13) 0.0518(10) 0.0035(9) 0.0184(9) 0.0086(11) C15 0.0744(14) 0.0861(16) 0.0688(13) 0.0019(11) 0.0293(11) 0.0330(12) C14 0.0564(11) 0.0662(11) 0.0618(11) 0.0105(9) 0.0182(9) 0.0273(9) C19 0.0453(8) 0.0421(8) 0.0449(8) 0.0113(6) 0.0078(6) 0.0136(7) C20 0.0606(12) 0.0526(11) 0.1068(17) 0.0121(11) 0.0363(12) 0.0213(9) C21 0.0829(16) 0.0529(12) 0.147(3) 0.0084(14) 0.0443(17) 0.0327(12) C22 0.0813(15) 0.0429(10) 0.1054(18) 0.0226(11) 0.0219(13) 0.0191(10) C23 0.0889(16) 0.0505(11) 0.0725(13) 0.0241(9) 0.0339(11) 0.0130(10) C24 0.0768(13) 0.0473(9) 0.0572(10) 0.0132(8) 0.0309(9) 0.0162(9) C11 0.0355(7) 0.0427(8) 0.0537(8) 0.0172(6) 0.0135(6) 0.0168(6) C7 0.0493(10) 0.0620(11) 0.0648(11) 0.0309(9) 0.0159(8) 0.0216(8) C6 0.0739(14) 0.0660(13) 0.0961(17) 0.0494(13) 0.0241(12) 0.0285(11) C5 0.0720(14) 0.0440(10) 0.1135(19) 0.0362(12) 0.0232(13) 0.0218(9) C4 0.0476(9) 0.0349(8) 0.0885(13) 0.0146(8) 0.0168(9) 0.0139(7) C3 0.0708(13) 0.0344(8) 0.1013(17) -0.0025(10) 0.0143(12) 0.0185(9) C2 0.0782(14) 0.0500(11) 0.0771(14) -0.0138(10) 0.0150(11) 0.0219(10) C1 0.0624(11) 0.0490(9) 0.0566(10) -0.0011(8) 0.0129(8) 0.0198(8) C12 0.0332(7) 0.0328(7) 0.0604(9) 0.0109(6) 0.0132(6) 0.0119(6) C8 0.0708(13) 0.0943(17) 0.0578(11) 0.0339(11) 0.0123(10) 0.0323(12) C9 0.0710(13) 0.0948(17) 0.0438(9) 0.0071(10) 0.0037(9) 0.0354(12) C10 0.0643(11) 0.0586(11) 0.0505(9) 0.0015(8) 0.0044(8) 0.0284(9) C25 0.0387(8) 0.0459(8) 0.0590(9) 0.0106(7) 0.0110(7) 0.0140(7) C26 0.0563(11) 0.0466(10) 0.0761(13) 0.0061(9) 0.0092(9) 0.0121(8) C27 0.0652(14) 0.0619(13) 0.0994(19) -0.0143(13) 0.0068(12) 0.0111(11) C28 0.0608(14) 0.112(2) 0.0711(15) -0.0166(15) 0.0019(11) 0.0235(14) C29 0.0630(13) 0.111(2) 0.0618(12) 0.0179(13) 0.0091(10) 0.0333(13) C30 0.0545(11) 0.0700(12) 0.0621(11) 0.0185(9) 0.0084(9) 0.0242(9) C31 0.0449(8) 0.0361(7) 0.0659(10) 0.0185(7) 0.0215(7) 0.0194(6) C36 0.0569(11) 0.0787(13) 0.0682(12) 0.0253(10) 0.0265(9) 0.0319(10) C35 0.0936(17) 0.0895(16) 0.0829(14) 0.0426(13) 0.0510(13) 0.0523(14) C34 0.0806(16) 0.0699(14) 0.119(2) 0.0416(14) 0.0655(15) 0.0357(12) C33 0.0474(11) 0.0883(17) 0.126(2) 0.0319(15) 0.0395(13) 0.0225(11) C32 0.0494(10) 0.0747(13) 0.0866(14) 0.0280(11) 0.0223(10) 0.0264(10) B1 0.0630(13) 0.0401(9) 0.0702(13) 0.0164(9) 0.0160(10) 0.0218(9) _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 Cu1 N2 2.0711(13) . ? Cu1 N1 2.1439(13) . ? Cu1 P1 2.2427(5) . ? Cu1 P2 2.2640(5) . ? P1 C13 1.8214(16) . ? P1 C19 1.8303(17) . ? P1 H29 1.363(19) . ? P2 C25 1.8361(18) . ? P2 C31 1.8414(17) . ? P2 B1 1.9480(19) . ? N2 C10 1.331(2) . ? N2 C11 1.3593(19) . ? N1 C1 1.334(2) . ? N1 C12 1.350(2) . ? C13 C14 1.383(2) . ? C13 C18 1.388(2) . ? C18 C17 1.383(3) . ? C18 H13 0.9300 . ? C17 C16 1.370(3) . ? C17 H12 0.9300 . ? C16 C15 1.365(3) . ? C16 H11 0.9300 . ? C15 C14 1.388(3) . ? C15 H10 0.9300 . ? C14 H9 0.9300 . ? C19 C20 1.371(3) . ? C19 C24 1.389(3) . ? C20 C21 1.396(3) . ? C20 H14 0.9300 . ? C21 C22 1.369(3) . ? C21 H15 0.9300 . ? C22 C23 1.374(3) . ? C22 H16 0.9300 . ? C23 C24 1.375(3) . ? C23 H17 0.9300 . ? C24 H18 0.9300 . ? C11 C7 1.407(2) . ? C11 C12 1.438(2) . ? C7 C8 1.394(3) . ? C7 C6 1.437(3) . ? C6 C5 1.329(3) . ? C6 H5 0.9300 . ? C5 C4 1.432(3) . ? C5 H4 0.9300 . ? C4 C3 1.404(3) . ? C4 C12 1.413(2) . ? C3 C2 1.350(3) . ? C3 H3 0.9300 . ? C2 C1 1.397(3) . ? C2 H2 0.9300 . ? C1 H1 0.9300 . ? C8 C9 1.355(3) . ? C8 H6 0.9300 . ? C9 C10 1.401(3) . ? C9 H7 0.9300 . ? C10 H8 0.9300 . ? C25 C30 1.392(3) . ? C25 C26 1.393(3) . ? C26 C27 1.387(3) . ? C26 H19 0.9300 . ? C27 C28 1.379(4) . ? C27 H20 0.9300 . ? C28 C29 1.366(4) . ? C28 H21 0.9300 . ? C29 C30 1.392(3) . ? C29 H22 0.9300 . ? C30 H23 0.9300 . ? C31 C36 1.377(3) . ? C31 C32 1.388(3) . ? C36 C35 1.396(3) . ? C36 H28 0.9300 . ? C35 C34 1.363(4) . ? C35 H27 0.9300 . ? C34 C33 1.364(4) . ? C34 H26 0.9300 . ? C33 C32 1.382(3) . ? C33 H25 0.9300 . ? C32 H24 0.9300 . ? B1 H1A 0.9600 . ? B1 H1B 0.9600 . ? B1 H1C 0.9600 . ? 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 N2 Cu1 N1 79.17(5) . . ? N2 Cu1 P1 114.27(4) . . ? N1 Cu1 P1 101.08(4) . . ? N2 Cu1 P2 118.20(4) . . ? N1 Cu1 P2 112.98(4) . . ? P1 Cu1 P2 121.105(19) . . ? C13 P1 C19 103.28(7) . . ? C13 P1 Cu1 109.10(5) . . ? C19 P1 Cu1 125.52(6) . . ? C13 P1 H29 97.8(8) . . ? C19 P1 H29 97.2(8) . . ? Cu1 P1 H29 119.7(8) . . ? C25 P2 C31 101.79(8) . . ? C25 P2 B1 108.42(9) . . ? C31 P2 B1 104.78(8) . . ? C25 P2 Cu1 108.02(5) . . ? C31 P2 Cu1 113.82(5) . . ? B1 P2 Cu1 118.63(7) . . ? C10 N2 C11 117.16(15) . . ? C10 N2 Cu1 128.93(12) . . ? C11 N2 Cu1 113.49(10) . . ? C1 N1 C12 117.90(14) . . ? C1 N1 Cu1 130.63(12) . . ? C12 N1 Cu1 111.37(10) . . ? C14 C13 C18 118.74(16) . . ? C14 C13 P1 123.33(14) . . ? C18 C13 P1 117.86(13) . . ? C17 C18 C13 120.27(18) . . ? C17 C18 H13 119.9 . . ? C13 C18 H13 119.9 . . ? C16 C17 C18 120.44(19) . . ? C16 C17 H12 119.8 . . ? C18 C17 H12 119.8 . . ? C15 C16 C17 119.89(19) . . ? C15 C16 H11 120.1 . . ? C17 C16 H11 120.1 . . ? C16 C15 C14 120.4(2) . . ? C16 C15 H10 119.8 . . ? C14 C15 H10 119.8 . . ? C13 C14 C15 120.24(19) . . ? C13 C14 H9 119.9 . . ? C15 C14 H9 119.9 . . ? C20 C19 C24 118.60(17) . . ? C20 C19 P1 120.47(14) . . ? C24 C19 P1 120.93(13) . . ? C19 C20 C21 120.1(2) . . ? C19 C20 H14 119.9 . . ? C21 C20 H14 119.9 . . ? C22 C21 C20 120.5(2) . . ? C22 C21 H15 119.8 . . ? C20 C21 H15 119.8 . . ? C21 C22 C23 119.7(2) . . ? C21 C22 H16 120.1 . . ? C23 C22 H16 120.1 . . ? C22 C23 C24 119.8(2) . . ? C22 C23 H17 120.1 . . ? C24 C23 H17 120.1 . . ? C23 C24 C19 121.23(18) . . ? C23 C24 H18 119.4 . . ? C19 C24 H18 119.4 . . ? N2 C11 C7 123.06(16) . . ? N2 C11 C12 117.29(13) . . ? C7 C11 C12 119.63(15) . . ? C8 C7 C11 117.24(18) . . ? C8 C7 C6 123.94(19) . . ? C11 C7 C6 118.82(19) . . ? C5 C6 C7 121.55(19) . . ? C5 C6 H5 119.2 . . ? C7 C6 H5 119.2 . . ? C6 C5 C4 121.55(18) . . ? C6 C5 H4 119.2 . . ? C4 C5 H4 119.2 . . ? C3 C4 C12 117.13(18) . . ? C3 C4 C5 124.06(18) . . ? C12 C4 C5 118.80(19) . . ? C2 C3 C4 119.84(17) . . ? C2 C3 H3 120.1 . . ? C4 C3 H3 120.1 . . ? C3 C2 C1 119.57(19) . . ? C3 C2 H2 120.2 . . ? C1 C2 H2 120.2 . . ? N1 C1 C2 122.76(19) . . ? N1 C1 H1 118.6 . . ? C2 C1 H1 118.6 . . ? N1 C12 C4 122.77(16) . . ? N1 C12 C11 117.60(13) . . ? C4 C12 C11 119.60(15) . . ? C9 C8 C7 120.25(18) . . ? C9 C8 H6 119.9 . . ? C7 C8 H6 119.9 . . ? C8 C9 C10 118.93(19) . . ? C8 C9 H7 120.5 . . ? C10 C9 H7 120.5 . . ? N2 C10 C9 123.31(19) . . ? N2 C10 H8 118.3 . . ? C9 C10 H8 118.3 . . ? C30 C25 C26 117.63(18) . . ? C30 C25 P2 121.32(14) . . ? C26 C25 P2 120.92(14) . . ? C27 C26 C25 121.2(2) . . ? C27 C26 H19 119.4 . . ? C25 C26 H19 119.4 . . ? C28 C27 C26 120.1(2) . . ? C28 C27 H20 120.0 . . ? C26 C27 H20 120.0 . . ? C29 C28 C27 119.7(2) . . ? C29 C28 H21 120.1 . . ? C27 C28 H21 120.1 . . ? C28 C29 C30 120.6(2) . . ? C28 C29 H22 119.7 . . ? C30 C29 H22 119.7 . . ? C25 C30 C29 120.8(2) . . ? C25 C30 H23 119.6 . . ? C29 C30 H23 119.6 . . ? C36 C31 C32 117.04(17) . . ? C36 C31 P2 120.74(13) . . ? C32 C31 P2 122.12(15) . . ? C31 C36 C35 122.2(2) . . ? C31 C36 H28 118.9 . . ? C35 C36 H28 118.9 . . ? C34 C35 C36 119.5(2) . . ? C34 C35 H27 120.3 . . ? C36 C35 H27 120.3 . . ? C35 C34 C33 119.3(2) . . ? C35 C34 H26 120.4 . . ? C33 C34 H26 120.4 . . ? C34 C33 C32 121.4(2) . . ? C34 C33 H25 119.3 . . ? C32 C33 H25 119.3 . . ? C33 C32 C31 120.6(2) . . ? C33 C32 H24 119.7 . . ? C31 C32 H24 119.7 . . ? P2 B1 H1A 109.5 . . ? P2 B1 H1B 109.5 . . ? H1A B1 H1B 109.5 . . ? P2 B1 H1C 109.5 . . ? H1A B1 H1C 109.5 . . ? H1B B1 H1C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.984 _diffrn_reflns_theta_full 29.14 _diffrn_measured_fraction_theta_full 0.984 _refine_diff_density_max 0.614 _refine_diff_density_min -0.243 _refine_diff_density_rms 0.068 _publ_section_abstract ; Copper-phosphido-borane complexes were synthesized and isolated for the first time. Their structure was experimentally and computationally investigated. They were shown to display catalytic activity in Csp-P bond formation. ; # Attachment 'CIFChemComm-4b.cif' data_4b _database_code_depnum_ccdc_archive 'CCDC 857697' #TrackingRef 'CIFChemComm-4b.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; Et2PHCuPPh2BH3phen ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C28 H32 B Cu N2 P2' _chemical_formula_sum 'C28 H32 B Cu N2 P2' _chemical_formula_weight 532.85 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' N N 0.0061 0.0033 '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' 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 Monoclinic _symmetry_space_group_name_H-M 'C2/c ' _symmetry_space_group_name_Hall '-C 2yc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 27.1263(5) _cell_length_b 13.9139(3) _cell_length_c 16.8585(3) _cell_angle_alpha 90.00 _cell_angle_beta 114.8520(10) _cell_angle_gamma 90.00 _cell_volume 5773.71(19) _cell_formula_units_Z 8 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 9786 _cell_measurement_theta_min 2.70 _cell_measurement_theta_max 30.49 _exptl_crystal_description block _exptl_crystal_colour orange _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.21 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.226 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2224 _exptl_absorpt_coefficient_mu 0.885 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 44477 _diffrn_reflns_av_R_equivalents 0.0259 _diffrn_reflns_av_sigmaI/netI 0.0176 _diffrn_reflns_limit_h_min -35 _diffrn_reflns_limit_h_max 36 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 1.92 _diffrn_reflns_theta_max 28.29 _reflns_number_total 7099 _reflns_number_gt 5932 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^ > 2sigma(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^)+(0.1000P)^2^+4.3620P] 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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 7099 _refine_ls_number_parameters 314 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0586 _refine_ls_R_factor_gt 0.0507 _refine_ls_wR_factor_ref 0.1615 _refine_ls_wR_factor_gt 0.1543 _refine_ls_goodness_of_fit_ref 1.131 _refine_ls_restrained_S_all 1.131 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 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 Cu1 Cu 0.144580(12) 0.33448(2) 0.248919(18) 0.03723(12) Uani 1 1 d . . . P2 P 0.17369(2) 0.26190(4) 0.15640(4) 0.03312(15) Uani 1 1 d . . . P1 P 0.07472(3) 0.43739(5) 0.18745(5) 0.05047(19) Uani 1 1 d . . . N1 N 0.19176(8) 0.38463(14) 0.37585(12) 0.0368(4) Uani 1 1 d . . . N2 N 0.12698(10) 0.22926(16) 0.32211(15) 0.0455(5) Uani 1 1 d . . . B1 B 0.17052(13) 0.12251(19) 0.1535(2) 0.0450(6) Uani 1 1 d . . . H1A H 0.1745 0.0992 0.1016 0.068 Uiso 1 1 calc R . . H1B H 0.1355 0.1013 0.1511 0.068 Uiso 1 1 calc R . . H1C H 0.1999 0.0966 0.2062 0.068 Uiso 1 1 calc R . . C19 C 0.13110(9) 0.30570(17) 0.04563(14) 0.0333(4) Uani 1 1 d . . . C13 C 0.24093(9) 0.29531(15) 0.16403(14) 0.0325(4) Uani 1 1 d . . . C20 C 0.13846(10) 0.39785(17) 0.01973(16) 0.0376(5) Uani 1 1 d . . . H20 H 0.1669 0.4372 0.0590 0.045 Uiso 1 1 calc R . . C12 C 0.18612(10) 0.32826(17) 0.43773(16) 0.0376(5) Uani 1 1 d . . . C4 C 0.21327(12) 0.3479(2) 0.52832(17) 0.0465(6) Uani 1 1 d . . . C18 C 0.27063(10) 0.37149(16) 0.21599(15) 0.0380(5) Uani 1 1 d . . . H18 H 0.2558 0.4073 0.2488 0.046 Uiso 1 1 calc R . . C21 C 0.10497(11) 0.4329(2) -0.06250(18) 0.0468(6) Uani 1 1 d . . . H21 H 0.1107 0.4956 -0.0792 0.056 Uiso 1 1 calc R . . C1 C 0.22384(11) 0.46079(18) 0.40307(17) 0.0430(5) Uani 1 1 d . . . H1 H 0.2282 0.5004 0.3605 0.052 Uiso 1 1 calc R . . C11 C 0.15207(10) 0.24533(18) 0.40891(17) 0.0400(5) Uani 1 1 d . . . C22 C 0.06370(11) 0.3773(3) -0.11952(19) 0.0545(7) Uani 1 1 d . . . H22 H 0.0405 0.4018 -0.1755 0.065 Uiso 1 1 calc R . . C24 C 0.08936(12) 0.2501(2) -0.01351(18) 0.0465(6) Uani 1 1 d . . . H24 H 0.0837 0.1869 0.0024 0.056 Uiso 1 1 calc R . . C2 C 0.25178(12) 0.4861(2) 0.49152(18) 0.0488(6) Uani 1 1 d . . . H2 H 0.2740 0.5419 0.5079 0.059 Uiso 1 1 calc R . . C3 C 0.24653(12) 0.4297(2) 0.55360(17) 0.0511(7) Uani 1 1 d . . . H3 H 0.2653 0.4456 0.6137 0.061 Uiso 1 1 calc R . . C16 C 0.34320(12) 0.3446(2) 0.1734(2) 0.0483(6) Uani 1 1 d . . . H16 H 0.3781 0.3611 0.1770 0.058 Uiso 1 1 calc R . . C5 C 0.20626(14) 0.2837(3) 0.58888(19) 0.0620(9) Uani 1 1 d . . . H5 H 0.2242 0.2968 0.6497 0.074 Uiso 1 1 calc R . . C17 C 0.32104(12) 0.39587(19) 0.22074(18) 0.0461(6) Uani 1 1 d . . . H17 H 0.3406 0.4480 0.2566 0.055 Uiso 1 1 calc R . . C7 C 0.14687(13) 0.1831(2) 0.4716(2) 0.0540(7) Uani 1 1 d . . . C8 C 0.11468(15) 0.1007(3) 0.4388(3) 0.0696(10) Uani 1 1 d . . . H8 H 0.1100 0.0565 0.4780 0.084 Uiso 1 1 calc R . . C6 C 0.17480(15) 0.2050(3) 0.5617(2) 0.0671(10) Uani 1 1 d . . . H6 H 0.1712 0.1634 0.6036 0.081 Uiso 1 1 calc R . . C10 C 0.09617(15) 0.1505(2) 0.2935(2) 0.0583(8) Uani 1 1 d . . . H10 H 0.0778 0.1394 0.2324 0.070 Uiso 1 1 calc R . . C14 C 0.26391(11) 0.24519(19) 0.11665(18) 0.0453(6) Uani 1 1 d . . . H14 H 0.2445 0.1931 0.0806 0.054 Uiso 1 1 calc R . . C15 C 0.31456(12) 0.2696(2) 0.1209(2) 0.0511(6) Uani 1 1 d . . . H15 H 0.3294 0.2348 0.0877 0.061 Uiso 1 1 calc R . . C23 C 0.05566(12) 0.2854(3) -0.09572(19) 0.0554(7) Uani 1 1 d . . . H23 H 0.0272 0.2466 -0.1355 0.067 Uiso 1 1 calc R . . C9 C 0.09026(16) 0.0838(2) 0.3515(3) 0.0699(10) Uani 1 1 d . . . H9 H 0.0693 0.0272 0.3297 0.084 Uiso 1 1 calc R . . C27 C 0.01637(14) 0.4004(3) 0.0883(2) 0.0733(11) Uani 1 1 d . . . H27A H -0.0110 0.4526 0.0701 0.088 Uiso 1 1 calc R . . H27B H 0.0283 0.3907 0.0409 0.088 Uiso 1 1 calc R . . C28 C -0.0093(2) 0.3105(5) 0.1003(4) 0.1094(18) Uani 1 1 d . . . H28A H 0.0173 0.2581 0.1165 0.164 Uiso 1 1 calc R . . H28B H -0.0405 0.2944 0.0456 0.164 Uiso 1 1 calc R . . H28C H -0.0216 0.3199 0.1468 0.164 Uiso 1 1 calc R . . C25 C 0.0856(2) 0.5539(3) 0.1474(4) 0.0926(14) Uani 1 1 d . . . H25A H 0.0878 0.5440 0.0908 0.111 Uiso 1 1 calc R . . H25B H 0.0536 0.5950 0.1362 0.111 Uiso 1 1 calc R . . C26 C 0.1303(2) 0.6012(5) 0.2012(5) 0.131(2) Uani 1 1 d . . . H26A H 0.1327 0.5993 0.2609 0.197 Uiso 1 1 calc R . . H26B H 0.1283 0.6681 0.1820 0.197 Uiso 1 1 calc R . . H26C H 0.1625 0.5705 0.2001 0.197 Uiso 1 1 calc R . . H29 H 0.0554(16) 0.456(3) 0.242(3) 0.081(12) 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 Cu1 0.0501(2) 0.03567(18) 0.03009(18) -0.00072(10) 0.02092(14) -0.00330(11) P2 0.0458(3) 0.0281(3) 0.0276(3) 0.00145(19) 0.0175(2) -0.0002(2) P1 0.0584(4) 0.0466(4) 0.0517(4) -0.0002(3) 0.0284(3) 0.0087(3) N1 0.0475(10) 0.0352(10) 0.0305(9) 0.0014(7) 0.0192(8) 0.0047(8) N2 0.0605(13) 0.0394(11) 0.0488(12) 0.0028(9) 0.0348(11) -0.0025(9) B1 0.0523(16) 0.0275(12) 0.0507(16) 0.0058(11) 0.0171(13) -0.0006(10) C19 0.0402(11) 0.0361(11) 0.0274(10) 0.0012(8) 0.0180(9) 0.0023(9) C13 0.0421(11) 0.0287(10) 0.0264(10) 0.0020(8) 0.0141(9) 0.0036(8) C20 0.0423(11) 0.0373(11) 0.0381(12) 0.0057(9) 0.0218(10) 0.0031(9) C12 0.0453(12) 0.0410(12) 0.0338(11) 0.0076(9) 0.0235(10) 0.0166(9) C4 0.0510(14) 0.0584(15) 0.0341(12) 0.0092(11) 0.0219(11) 0.0234(12) C18 0.0534(13) 0.0304(10) 0.0339(11) -0.0041(8) 0.0220(10) 0.0004(9) C21 0.0499(14) 0.0509(14) 0.0460(14) 0.0190(11) 0.0266(12) 0.0099(11) C1 0.0559(14) 0.0367(12) 0.0375(12) -0.0022(9) 0.0206(11) 0.0026(10) C11 0.0481(13) 0.0396(12) 0.0433(13) 0.0111(9) 0.0299(11) 0.0130(9) C22 0.0455(14) 0.077(2) 0.0383(14) 0.0164(13) 0.0154(12) 0.0087(14) C24 0.0534(14) 0.0426(13) 0.0418(13) 0.0001(10) 0.0185(12) -0.0042(10) C2 0.0539(15) 0.0434(13) 0.0415(13) -0.0079(10) 0.0126(11) 0.0069(11) C3 0.0566(15) 0.0613(17) 0.0300(12) -0.0055(11) 0.0129(11) 0.0192(13) C16 0.0488(14) 0.0477(14) 0.0544(16) -0.0002(11) 0.0274(13) 0.0005(11) C5 0.0643(18) 0.091(2) 0.0354(14) 0.0244(15) 0.0253(13) 0.0275(18) C17 0.0564(14) 0.0362(12) 0.0473(14) -0.0069(10) 0.0234(12) -0.0053(10) C7 0.0577(16) 0.0592(16) 0.0595(17) 0.0269(14) 0.0387(14) 0.0181(13) C8 0.079(2) 0.0577(18) 0.093(3) 0.0304(18) 0.057(2) 0.0057(16) C6 0.071(2) 0.088(2) 0.0547(18) 0.0353(18) 0.0374(17) 0.0186(19) C10 0.073(2) 0.0454(15) 0.071(2) -0.0042(14) 0.0439(17) -0.0129(13) C14 0.0523(14) 0.0411(12) 0.0436(13) -0.0121(10) 0.0212(12) 0.0009(10) C15 0.0567(15) 0.0515(15) 0.0533(16) -0.0097(12) 0.0312(13) 0.0072(12) C23 0.0471(15) 0.0703(19) 0.0394(14) -0.0003(13) 0.0090(12) -0.0042(13) C9 0.087(2) 0.0467(16) 0.101(3) 0.0082(17) 0.064(2) -0.0103(16) C27 0.0591(18) 0.111(3) 0.0477(17) 0.0003(18) 0.0202(15) 0.031(2) C28 0.078(3) 0.130(4) 0.095(4) -0.012(3) 0.011(3) -0.026(3) C25 0.097(3) 0.059(2) 0.132(4) 0.017(2) 0.058(3) 0.010(2) C26 0.091(3) 0.108(4) 0.184(7) 0.052(5) 0.048(4) -0.003(3) _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 Cu1 N2 2.095(2) . ? Cu1 N1 2.098(2) . ? Cu1 P1 2.2505(8) . ? Cu1 P2 2.2609(6) . ? P2 C13 1.833(2) . ? P2 C19 1.838(2) . ? P2 B1 1.941(3) . ? P1 C27 1.827(4) . ? P1 C25 1.828(4) . ? P1 H29 1.26(4) . ? N1 C1 1.325(3) . ? N1 C12 1.364(3) . ? N2 C10 1.339(4) . ? N2 C11 1.348(4) . ? B1 H1A 0.9800 . ? B1 H1B 0.9800 . ? B1 H1C 0.9800 . ? C19 C24 1.388(4) . ? C19 C20 1.396(3) . ? C13 C14 1.390(3) . ? C13 C18 1.395(3) . ? C20 C21 1.388(3) . ? C20 H20 0.9500 . ? C12 C4 1.416(4) . ? C12 C11 1.430(4) . ? C4 C3 1.402(4) . ? C4 C5 1.429(4) . ? C18 C17 1.378(4) . ? C18 H18 0.9500 . ? C21 C22 1.367(4) . ? C21 H21 0.9500 . ? C1 C2 1.404(4) . ? C1 H1 0.9500 . ? C11 C7 1.418(3) . ? C22 C23 1.385(5) . ? C22 H22 0.9500 . ? C24 C23 1.390(4) . ? C24 H24 0.9500 . ? C2 C3 1.363(4) . ? C2 H2 0.9500 . ? C3 H3 0.9500 . ? C16 C15 1.377(4) . ? C16 C17 1.382(4) . ? C16 H16 0.9500 . ? C5 C6 1.344(6) . ? C5 H5 0.9500 . ? C17 H17 0.9500 . ? C7 C8 1.406(5) . ? C7 C6 1.416(5) . ? C8 C9 1.356(6) . ? C8 H8 0.9500 . ? C6 H6 0.9500 . ? C10 C9 1.405(4) . ? C10 H10 0.9500 . ? C14 C15 1.388(4) . ? C14 H14 0.9500 . ? C15 H15 0.9500 . ? C23 H23 0.9500 . ? C9 H9 0.9500 . ? C27 C28 1.486(7) . ? C27 H27A 0.9900 . ? C27 H27B 0.9900 . ? C28 H28A 0.9800 . ? C28 H28B 0.9800 . ? C28 H28C 0.9800 . ? C25 C26 1.342(8) . ? C25 H25A 0.9900 . ? C25 H25B 0.9900 . ? C26 H26A 0.9800 . ? C26 H26B 0.9800 . ? C26 H26C 0.9800 . ? 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 N2 Cu1 N1 79.86(9) . . ? N2 Cu1 P1 111.07(7) . . ? N1 Cu1 P1 107.02(6) . . ? N2 Cu1 P2 109.05(6) . . ? N1 Cu1 P2 127.73(6) . . ? P1 Cu1 P2 115.93(3) . . ? C13 P2 C19 99.74(10) . . ? C13 P2 B1 106.70(12) . . ? C19 P2 B1 107.64(12) . . ? C13 P2 Cu1 117.64(7) . . ? C19 P2 Cu1 107.46(7) . . ? B1 P2 Cu1 116.06(10) . . ? C27 P1 C25 97.1(2) . . ? C27 P1 Cu1 118.70(13) . . ? C25 P1 Cu1 119.91(16) . . ? C27 P1 H29 105.1(18) . . ? C25 P1 H29 105.4(19) . . ? Cu1 P1 H29 108.9(19) . . ? C1 N1 C12 117.6(2) . . ? C1 N1 Cu1 130.51(16) . . ? C12 N1 Cu1 111.86(17) . . ? C10 N2 C11 118.7(2) . . ? C10 N2 Cu1 128.5(2) . . ? C11 N2 Cu1 112.79(17) . . ? P2 B1 H1A 109.5 . . ? P2 B1 H1B 109.5 . . ? H1A B1 H1B 109.5 . . ? P2 B1 H1C 109.5 . . ? H1A B1 H1C 109.5 . . ? H1B B1 H1C 109.5 . . ? C24 C19 C20 117.9(2) . . ? C24 C19 P2 121.31(19) . . ? C20 C19 P2 120.72(18) . . ? C14 C13 C18 117.5(2) . . ? C14 C13 P2 120.38(18) . . ? C18 C13 P2 122.11(17) . . ? C21 C20 C19 121.0(2) . . ? C21 C20 H20 119.5 . . ? C19 C20 H20 119.5 . . ? N1 C12 C4 122.6(2) . . ? N1 C12 C11 117.9(2) . . ? C4 C12 C11 119.4(2) . . ? C3 C4 C12 117.5(2) . . ? C3 C4 C5 123.5(3) . . ? C12 C4 C5 119.0(3) . . ? C17 C18 C13 121.4(2) . . ? C17 C18 H18 119.3 . . ? C13 C18 H18 119.3 . . ? C22 C21 C20 120.2(3) . . ? C22 C21 H21 119.9 . . ? C20 C21 H21 119.9 . . ? N1 C1 C2 123.5(2) . . ? N1 C1 H1 118.3 . . ? C2 C1 H1 118.3 . . ? N2 C11 C7 123.0(3) . . ? N2 C11 C12 117.5(2) . . ? C7 C11 C12 119.5(3) . . ? C21 C22 C23 120.0(2) . . ? C21 C22 H22 120.0 . . ? C23 C22 H22 120.0 . . ? C19 C24 C23 121.0(3) . . ? C19 C24 H24 119.5 . . ? C23 C24 H24 119.5 . . ? C3 C2 C1 119.1(3) . . ? C3 C2 H2 120.4 . . ? C1 C2 H2 120.4 . . ? C2 C3 C4 119.7(2) . . ? C2 C3 H3 120.1 . . ? C4 C3 H3 120.1 . . ? C15 C16 C17 119.8(3) . . ? C15 C16 H16 120.1 . . ? C17 C16 H16 120.1 . . ? C6 C5 C4 121.4(3) . . ? C6 C5 H5 119.3 . . ? C4 C5 H5 119.3 . . ? C18 C17 C16 120.1(2) . . ? C18 C17 H17 120.0 . . ? C16 C17 H17 120.0 . . ? C8 C7 C6 124.2(3) . . ? C8 C7 C11 116.4(3) . . ? C6 C7 C11 119.4(3) . . ? C9 C8 C7 120.5(3) . . ? C9 C8 H8 119.7 . . ? C7 C8 H8 119.7 . . ? C5 C6 C7 121.2(3) . . ? C5 C6 H6 119.4 . . ? C7 C6 H6 119.4 . . ? N2 C10 C9 121.7(3) . . ? N2 C10 H10 119.1 . . ? C9 C10 H10 119.1 . . ? C15 C14 C13 121.4(2) . . ? C15 C14 H14 119.3 . . ? C13 C14 H14 119.3 . . ? C16 C15 C14 119.8(2) . . ? C16 C15 H15 120.1 . . ? C14 C15 H15 120.1 . . ? C22 C23 C24 119.8(3) . . ? C22 C23 H23 120.1 . . ? C24 C23 H23 120.1 . . ? C8 C9 C10 119.6(3) . . ? C8 C9 H9 120.2 . . ? C10 C9 H9 120.2 . . ? C28 C27 P1 112.8(3) . . ? C28 C27 H27A 109.0 . . ? P1 C27 H27A 109.0 . . ? C28 C27 H27B 109.0 . . ? P1 C27 H27B 109.0 . . ? H27A C27 H27B 107.8 . . ? C27 C28 H28A 109.5 . . ? C27 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? C27 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? C26 C25 P1 115.2(4) . . ? C26 C25 H25A 108.5 . . ? P1 C25 H25A 108.5 . . ? C26 C25 H25B 108.5 . . ? P1 C25 H25B 108.5 . . ? H25A C25 H25B 107.5 . . ? C25 C26 H26A 109.5 . . ? C25 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? C25 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons 1 0.500 0.000 0.393 335.9 56.7 2 0.000 0.500 0.130 335.8 56.7 _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 28.29 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 1.353 _refine_diff_density_min -0.626 _refine_diff_density_rms 0.125