# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2011 data_global _journal_coden_Cambridge 182 _journal_volume ? _journal_page_first ? _journal_year ? loop_ _publ_author_name 'Hahn, Ekkehardt' 'Kosterke, Tim' 'Pape, Tania' _publ_contact_author_name 'Dr Ekkehardt Hahn' _publ_contact_author_email fehahn@uni-muenster.de _publ_section_title ; Synthesis of complexes bearing NH,NMe-substituted NHCs by oxidative addition of 2-halogenato-N-methylbenzimidazoles to Ni0+ ; # Attachment '- [2](BF4)0.5Cl0.5x0.5C7H8.cif' data_sad1 _database_code_depnum_ccdc_archive 'CCDC 834828' #TrackingRef '- [2](BF4)0.5Cl0.5x0.5C7H8.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C37.50 H36 B0.50 Cl0.50 F2 I N2 Ni P2' _chemical_formula_weight 823.36 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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' Ni Ni 0.3393 1.1124 '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' Cl Cl 0.1484 0.1585 '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 9.5503(3) _cell_length_b 10.1764(3) _cell_length_c 20.2212(6) _cell_angle_alpha 84.7210(10) _cell_angle_beta 81.8170(10) _cell_angle_gamma 69.2620(10) _cell_volume 1817.37(10) _cell_formula_units_Z 2 _cell_measurement_temperature 153(2) _cell_measurement_reflns_used 900 _cell_measurement_theta_min 1 _cell_measurement_theta_max 22.5 _exptl_crystal_description 'transparent prism' _exptl_crystal_colour red-brown _exptl_crystal_size_max 0.06 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.505 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 830 _exptl_absorpt_coefficient_mu 1.547 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9129 _exptl_absorpt_correction_T_max 0.9551 _exptl_absorpt_process_details ; Corrections were done with the SADABS program, utilizing the none merged raw data obtained from the integration process. Integration and final cell refinement were done with SAINT. SADABS reports ratio of Tmin/Tmax = 0.758000 ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 153(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'Omega and Phi scans' _diffrn_detector_area_resol_mean 80 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 21343 _diffrn_reflns_av_R_equivalents 0.0243 _diffrn_reflns_av_sigmaI/netI 0.0416 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_theta_min 1.02 _diffrn_reflns_theta_max 30.00 _reflns_number_total 10447 _reflns_number_gt 8065 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2(Bruker AXS, 2007)' _computing_cell_refinement 'APEX2(Bruker AXS, 2007)' _computing_data_reduction 'SAINT,SADABS (Bruker AXS, 2007 )' _computing_structure_solution ; SHELXS-97 , G. M. Sheldrick, Acta Cryst. (2008) A64, 112-122 ; _computing_structure_refinement ; SHELXL-97, G. M. Sheldrick, Acta Cryst. (2008) A64, 112-122 ; _computing_molecular_graphics ; ORTEP3,L.J. Farrugia, J. Appl. Cryst. (1997) 30, 565 ; _computing_publication_material ? _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^)+(0.1108P)^2^+5.0743P] 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 noref _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 10447 _refine_ls_number_parameters 423 _refine_ls_number_restraints 9 _refine_ls_R_factor_all 0.0795 _refine_ls_R_factor_gt 0.0605 _refine_ls_wR_factor_ref 0.1899 _refine_ls_wR_factor_gt 0.1739 _refine_ls_goodness_of_fit_ref 1.058 _refine_ls_restrained_S_all 1.059 _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 I1 I 0.32654(3) 0.21065(3) 0.624036(15) 0.02841(11) Uani 1 1 d . . . Ni1 Ni 0.54366(6) 0.14830(6) 0.69187(3) 0.01913(13) Uani 1 1 d . . . P1 P 0.72022(13) 0.13954(12) 0.74923(6) 0.0204(2) Uani 1 1 d . . . P2 P 0.72175(12) 0.08259(12) 0.60698(6) 0.0200(2) Uani 1 1 d . . . N1 N 0.3634(4) 0.0543(4) 0.7957(2) 0.0247(8) Uani 1 1 d . . . N2 N 0.3098(4) 0.2774(4) 0.8036(2) 0.0246(8) Uani 1 1 d . . . H2 H 0.3147 0.3624 0.7973 0.030 Uiso 1 1 calc R . . C1 C 0.4020(5) 0.1649(5) 0.7694(2) 0.0215(8) Uani 1 1 d . . . C2 C 0.2386(6) 0.0973(6) 0.8446(2) 0.0289(10) Uani 1 1 d . . . C3 C 0.2060(5) 0.2407(6) 0.8502(2) 0.0280(10) Uani 1 1 d . . . C4 C 0.0861(6) 0.3190(7) 0.8942(3) 0.0387(13) Uani 1 1 d . . . H4 H 0.0643 0.4163 0.8996 0.046 Uiso 1 1 calc R . . C5 C -0.0001(7) 0.2440(9) 0.9301(3) 0.0506(18) Uani 1 1 d . . . H5 H -0.0831 0.2926 0.9610 0.061 Uiso 1 1 calc R . . C6 C 0.0297(7) 0.1026(9) 0.9225(3) 0.0484(17) Uani 1 1 d . . . H6 H -0.0350 0.0582 0.9472 0.058 Uiso 1 1 calc R . . C7 C 0.1513(7) 0.0243(7) 0.8799(3) 0.0400(13) Uani 1 1 d . . . H7 H 0.1738 -0.0733 0.8752 0.048 Uiso 1 1 calc R . . C8 C 0.4377(7) -0.0896(6) 0.7746(3) 0.0386(12) Uani 1 1 d . . . H8A H 0.5136 -0.0916 0.7363 0.058 Uiso 1 1 calc R . . H8B H 0.3628 -0.1250 0.7619 0.058 Uiso 1 1 calc R . . H8C H 0.4867 -0.1492 0.8116 0.058 Uiso 1 1 calc R . . C9 C 0.7160(5) 0.0737(5) 0.8350(2) 0.0236(9) Uani 1 1 d . . . C10 C 0.6380(6) 0.1649(6) 0.8864(3) 0.0317(10) Uani 1 1 d . . . H10 H 0.5927 0.2628 0.8763 0.038 Uiso 1 1 calc R . . C11 C 0.6271(6) 0.1119(7) 0.9520(3) 0.0364(12) Uani 1 1 d . . . H11 H 0.5732 0.1740 0.9866 0.044 Uiso 1 1 calc R . . C12 C 0.6936(7) -0.0297(7) 0.9675(3) 0.0391(13) Uani 1 1 d . . . H12 H 0.6851 -0.0651 1.0125 0.047 Uiso 1 1 calc R . . C13 C 0.7735(7) -0.1207(7) 0.9166(3) 0.0414(13) Uani 1 1 d . . . H13 H 0.8202 -0.2181 0.9271 0.050 Uiso 1 1 calc R . . C14 C 0.7851(6) -0.0698(6) 0.8507(3) 0.0342(11) Uani 1 1 d . . . H14 H 0.8398 -0.1322 0.8163 0.041 Uiso 1 1 calc R . . C15 C 0.7251(5) 0.3163(5) 0.7481(2) 0.0236(8) Uani 1 1 d . . . C16 C 0.6114(5) 0.4293(5) 0.7224(2) 0.0267(9) Uani 1 1 d . . . H16 H 0.5271 0.4151 0.7084 0.032 Uiso 1 1 calc R . . C17 C 0.6216(6) 0.5626(5) 0.7171(3) 0.0327(11) Uani 1 1 d . . . H17 H 0.5434 0.6400 0.7002 0.039 Uiso 1 1 calc R . . C18 C 0.7458(7) 0.5833(6) 0.7365(3) 0.0357(12) Uani 1 1 d . . . H18 H 0.7530 0.6746 0.7320 0.043 Uiso 1 1 calc R . . C19 C 0.8591(7) 0.4716(6) 0.7622(3) 0.0418(13) Uani 1 1 d . . . H19 H 0.9438 0.4861 0.7754 0.050 Uiso 1 1 calc R . . C20 C 0.8486(6) 0.3378(6) 0.7686(3) 0.0343(11) Uani 1 1 d . . . H20 H 0.9256 0.2612 0.7868 0.041 Uiso 1 1 calc R . . C21 C 0.9050(5) 0.0405(5) 0.7047(2) 0.0243(9) Uani 1 1 d . . . H21A H 0.9868 0.0601 0.7224 0.029 Uiso 1 1 calc R . . H21B H 0.9242 -0.0618 0.7097 0.029 Uiso 1 1 calc R . . C22 C 0.8964(5) 0.0912(5) 0.6315(2) 0.0234(8) Uani 1 1 d . . . H22A H 0.9849 0.0307 0.6032 0.028 Uiso 1 1 calc R . . H22B H 0.8960 0.1890 0.6257 0.028 Uiso 1 1 calc R . . C23 C 0.7054(5) 0.1760(5) 0.5259(2) 0.0213(8) Uani 1 1 d . . . C24 C 0.6773(5) 0.3205(5) 0.5237(3) 0.0280(9) Uani 1 1 d . . . H24 H 0.6615 0.3676 0.5641 0.034 Uiso 1 1 calc R . . C25 C 0.6725(6) 0.3958(6) 0.4625(3) 0.0308(10) Uani 1 1 d . . . H25 H 0.6541 0.4940 0.4614 0.037 Uiso 1 1 calc R . . C26 C 0.6943(5) 0.3289(6) 0.4034(3) 0.0308(10) Uani 1 1 d . . . H26 H 0.6930 0.3803 0.3616 0.037 Uiso 1 1 calc R . . C27 C 0.7183(5) 0.1845(5) 0.4056(2) 0.0262(9) Uani 1 1 d . . . H27 H 0.7301 0.1383 0.3654 0.031 Uiso 1 1 calc R . . C28 C 0.7249(5) 0.1092(5) 0.4662(2) 0.0237(9) Uani 1 1 d . . . H28 H 0.7429 0.0111 0.4673 0.028 Uiso 1 1 calc R . . C29 C 0.7625(5) -0.1018(5) 0.5914(2) 0.0218(8) Uani 1 1 d . . . C30 C 0.6476(5) -0.1431(5) 0.5748(2) 0.0251(9) Uani 1 1 d . . . H30 H 0.5489 -0.0762 0.5735 0.030 Uiso 1 1 calc R . . C31 C 0.6775(6) -0.2818(5) 0.5602(3) 0.0291(10) Uani 1 1 d . . . H31 H 0.5984 -0.3091 0.5493 0.035 Uiso 1 1 calc R . . C32 C 0.8195(6) -0.3800(6) 0.5613(3) 0.0318(10) Uani 1 1 d . . . H32 H 0.8395 -0.4738 0.5495 0.038 Uiso 1 1 calc R . . C33 C 0.9350(6) -0.3412(6) 0.5798(3) 0.0357(12) Uani 1 1 d . . . H33 H 1.0325 -0.4096 0.5825 0.043 Uiso 1 1 calc R . . C34 C 0.9069(6) -0.2026(5) 0.5943(3) 0.0328(11) Uani 1 1 d . . . H34 H 0.9856 -0.1761 0.6061 0.039 Uiso 1 1 calc R . . B1 B 0.17047(16) 0.65778(14) 0.78561(8) 0.0132(3) Uani 0.50 1 d PD . . F1 F 0.0884(9) 0.6400(9) 0.8441(3) 0.079(4) Uani 0.50 1 d PD . . F2 F 0.0507(6) 0.6845(7) 0.7511(4) 0.077(3) Uani 0.50 1 d PD . . F3 F 0.2779(6) 0.5430(4) 0.7584(3) 0.0357(15) Uani 0.50 1 d PD . . F4 F 0.1813(8) 0.7876(3) 0.7751(4) 0.0478(19) Uani 0.50 1 d PD . . Cl2 Cl 0.17047(16) 0.65778(14) 0.78561(8) 0.0132(3) Uani 0.50 1 d P . . C41 C 0.4006(13) 0.5088(14) 0.9649(7) 0.109(3) Uiso 1 1 d D . . C42 C 0.6149(14) 0.5821(14) 0.9201(7) 0.109(3) Uiso 1 1 d D . . C43 C 0.539(2) 0.519(3) 0.9718(9) 0.109(3) Uiso 0.50 1 d PD . . C44 C 0.478(2) 0.567(3) 0.9143(9) 0.109(3) Uiso 0.50 1 d PD . . C45 C 0.677(3) 0.552(3) 0.9802(9) 0.109(3) Uiso 0.50 1 d PD . . 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 0.02284(16) 0.03607(19) 0.02663(17) -0.00358(12) -0.00665(11) -0.00861(13) Ni1 0.0164(3) 0.0224(3) 0.0192(3) -0.0032(2) -0.0011(2) -0.0073(2) P1 0.0188(5) 0.0217(5) 0.0210(5) -0.0024(4) -0.0038(4) -0.0068(4) P2 0.0183(5) 0.0223(5) 0.0206(5) -0.0040(4) -0.0005(4) -0.0084(4) N1 0.0246(19) 0.0256(19) 0.0240(18) -0.0009(15) 0.0010(15) -0.0105(16) N2 0.0230(18) 0.0244(19) 0.0236(18) -0.0042(14) 0.0035(14) -0.0064(15) C1 0.0202(19) 0.024(2) 0.0196(19) -0.0020(15) -0.0030(15) -0.0063(16) C2 0.027(2) 0.040(3) 0.024(2) 0.0005(19) -0.0027(18) -0.017(2) C3 0.024(2) 0.037(3) 0.021(2) -0.0011(18) -0.0012(17) -0.008(2) C4 0.027(2) 0.051(3) 0.028(3) -0.005(2) 0.003(2) -0.003(2) C5 0.029(3) 0.086(5) 0.026(3) 0.003(3) 0.004(2) -0.011(3) C6 0.032(3) 0.087(5) 0.027(3) 0.014(3) -0.002(2) -0.027(3) C7 0.040(3) 0.059(4) 0.028(3) 0.010(2) -0.005(2) -0.028(3) C8 0.045(3) 0.023(2) 0.048(3) -0.004(2) 0.004(3) -0.016(2) C9 0.021(2) 0.028(2) 0.022(2) -0.0001(16) -0.0051(16) -0.0075(17) C10 0.031(2) 0.033(3) 0.030(2) -0.006(2) 0.000(2) -0.009(2) C11 0.031(3) 0.054(3) 0.027(2) -0.008(2) 0.000(2) -0.017(2) C12 0.035(3) 0.059(4) 0.029(3) 0.010(2) -0.005(2) -0.024(3) C13 0.047(3) 0.041(3) 0.035(3) 0.010(2) -0.007(2) -0.016(3) C14 0.038(3) 0.031(3) 0.031(3) 0.001(2) -0.002(2) -0.010(2) C15 0.024(2) 0.024(2) 0.024(2) -0.0025(16) -0.0046(17) -0.0092(17) C16 0.024(2) 0.029(2) 0.028(2) -0.0039(18) -0.0028(17) -0.0093(18) C17 0.034(3) 0.025(2) 0.038(3) 0.000(2) -0.005(2) -0.009(2) C18 0.040(3) 0.024(2) 0.047(3) 0.001(2) -0.007(2) -0.016(2) C19 0.043(3) 0.038(3) 0.055(4) 0.002(3) -0.019(3) -0.022(3) C20 0.032(3) 0.029(3) 0.045(3) 0.001(2) -0.017(2) -0.011(2) C21 0.0185(19) 0.026(2) 0.026(2) -0.0034(17) -0.0038(16) -0.0036(17) C22 0.021(2) 0.025(2) 0.026(2) -0.0042(16) -0.0005(16) -0.0102(17) C23 0.0183(19) 0.025(2) 0.023(2) -0.0044(16) -0.0020(15) -0.0094(16) C24 0.025(2) 0.026(2) 0.033(2) -0.0049(18) 0.0004(19) -0.0105(19) C25 0.024(2) 0.028(2) 0.040(3) 0.002(2) -0.003(2) -0.0091(19) C26 0.018(2) 0.040(3) 0.033(2) 0.007(2) -0.0042(18) -0.0106(19) C27 0.020(2) 0.037(3) 0.022(2) -0.0031(18) -0.0029(16) -0.0099(19) C28 0.021(2) 0.026(2) 0.025(2) -0.0056(17) -0.0012(16) -0.0092(17) C29 0.0199(19) 0.024(2) 0.024(2) -0.0038(16) 0.0000(16) -0.0104(16) C30 0.021(2) 0.027(2) 0.028(2) -0.0031(17) -0.0034(17) -0.0087(17) C31 0.030(2) 0.032(2) 0.030(2) -0.0051(19) -0.0028(19) -0.016(2) C32 0.028(2) 0.029(2) 0.041(3) -0.009(2) 0.001(2) -0.015(2) C33 0.022(2) 0.028(3) 0.056(3) -0.010(2) -0.002(2) -0.0069(19) C34 0.023(2) 0.029(2) 0.048(3) -0.008(2) -0.003(2) -0.0106(19) B1 0.0138(6) 0.0038(5) 0.0210(7) -0.0020(5) 0.0035(5) -0.0037(5) F1 0.076(6) 0.070(6) 0.032(4) 0.022(4) 0.033(4) 0.027(5) F2 0.094(7) 0.027(4) 0.109(8) -0.029(4) 0.045(6) -0.035(4) F3 0.026(3) 0.014(2) 0.049(4) 0.010(2) 0.011(3) 0.006(2) F4 0.039(4) 0.014(3) 0.100(6) -0.011(3) -0.014(4) -0.016(3) Cl2 0.0138(6) 0.0038(5) 0.0210(7) -0.0020(5) 0.0035(5) -0.0037(5) _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 Ni1 2.5102(6) . ? Ni1 C1 1.898(4) . ? Ni1 P1 2.1513(12) . ? Ni1 P2 2.2048(12) . ? P1 C9 1.801(5) . ? P1 C15 1.814(5) . ? P1 C21 1.843(5) . ? P2 C23 1.815(5) . ? P2 C29 1.825(5) . ? P2 C22 1.839(5) . ? N1 C1 1.347(6) . ? N1 C2 1.401(6) . ? N1 C8 1.457(7) . ? N2 C1 1.350(6) . ? N2 C3 1.393(6) . ? C2 C7 1.389(7) . ? C2 C3 1.392(7) . ? C3 C4 1.391(7) . ? C4 C5 1.399(9) . ? C5 C6 1.384(11) . ? C6 C7 1.383(9) . ? C9 C14 1.400(7) . ? C9 C10 1.401(7) . ? C10 C11 1.390(8) . ? C11 C12 1.380(9) . ? C12 C13 1.396(9) . ? C13 C14 1.389(8) . ? C15 C16 1.393(7) . ? C15 C20 1.395(7) . ? C16 C17 1.388(7) . ? C17 C18 1.389(8) . ? C18 C19 1.383(8) . ? C19 C20 1.393(8) . ? C21 C22 1.526(6) . ? C23 C24 1.396(7) . ? C23 C28 1.397(6) . ? C24 C25 1.391(7) . ? C25 C26 1.385(8) . ? C26 C27 1.403(7) . ? C27 C28 1.380(7) . ? C29 C30 1.396(6) . ? C29 C34 1.402(7) . ? C30 C31 1.388(7) . ? C31 C32 1.373(7) . ? C32 C33 1.403(7) . ? C33 C34 1.389(7) . ? B1 F3 1.3517(10) . ? B1 F4 1.3562(10) . ? B1 F1 1.3570(10) . ? B1 F2 1.3577(10) . ? C41 C43 1.3898(10) . ? C41 C44 1.3903(10) . ? C41 C43 1.44(2) 2_667 ? C41 C45 1.46(3) 2_667 ? C42 C44 1.3900(10) . ? C42 C45 1.3901(10) . ? C42 C43 1.4200(10) . ? C43 C44 1.35(3) . ? C43 C43 1.38(3) 2_667 ? C43 C41 1.44(2) 2_667 ? C43 C45 1.51(3) . ? C45 C41 1.46(3) 2_667 ? 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 C1 Ni1 P1 92.47(14) . . ? C1 Ni1 P2 168.28(14) . . ? P1 Ni1 P2 86.43(5) . . ? C1 Ni1 I1 87.53(13) . . ? P1 Ni1 I1 168.52(4) . . ? P2 Ni1 I1 95.85(4) . . ? C9 P1 C15 107.5(2) . . ? C9 P1 C21 108.0(2) . . ? C15 P1 C21 103.2(2) . . ? C9 P1 Ni1 119.86(15) . . ? C15 P1 Ni1 107.29(15) . . ? C21 P1 Ni1 109.75(15) . . ? C23 P2 C29 106.2(2) . . ? C23 P2 C22 103.9(2) . . ? C29 P2 C22 105.6(2) . . ? C23 P2 Ni1 121.87(15) . . ? C29 P2 Ni1 110.07(15) . . ? C22 P2 Ni1 108.01(15) . . ? C1 N1 C2 110.7(4) . . ? C1 N1 C8 124.7(4) . . ? C2 N1 C8 124.6(4) . . ? C1 N2 C3 110.9(4) . . ? N1 C1 N2 106.4(4) . . ? N1 C1 Ni1 121.1(3) . . ? N2 C1 Ni1 132.0(3) . . ? C7 C2 C3 122.9(5) . . ? C7 C2 N1 131.2(5) . . ? C3 C2 N1 105.9(4) . . ? C4 C3 C2 121.5(5) . . ? C4 C3 N2 132.5(5) . . ? C2 C3 N2 106.0(4) . . ? C3 C4 C5 115.1(6) . . ? C6 C5 C4 123.1(6) . . ? C7 C6 C5 121.6(6) . . ? C6 C7 C2 115.8(6) . . ? C14 C9 C10 119.4(5) . . ? C14 C9 P1 120.4(4) . . ? C10 C9 P1 120.1(4) . . ? C11 C10 C9 119.9(5) . . ? C12 C11 C10 120.8(5) . . ? C11 C12 C13 119.5(5) . . ? C14 C13 C12 120.5(6) . . ? C13 C14 C9 119.9(5) . . ? C16 C15 C20 119.8(4) . . ? C16 C15 P1 120.1(4) . . ? C20 C15 P1 119.9(4) . . ? C17 C16 C15 119.8(5) . . ? C16 C17 C18 120.3(5) . . ? C19 C18 C17 120.2(5) . . ? C18 C19 C20 119.9(5) . . ? C19 C20 C15 120.0(5) . . ? C22 C21 P1 105.5(3) . . ? C21 C22 P2 108.0(3) . . ? C24 C23 C28 119.1(4) . . ? C24 C23 P2 117.7(3) . . ? C28 C23 P2 123.1(4) . . ? C25 C24 C23 120.1(5) . . ? C26 C25 C24 120.6(5) . . ? C25 C26 C27 119.3(5) . . ? C28 C27 C26 120.2(4) . . ? C27 C28 C23 120.7(4) . . ? C30 C29 C34 119.1(4) . . ? C30 C29 P2 119.1(4) . . ? C34 C29 P2 121.8(3) . . ? C31 C30 C29 120.1(4) . . ? C32 C31 C30 121.0(5) . . ? C31 C32 C33 119.6(5) . . ? C34 C33 C32 120.0(5) . . ? C33 C34 C29 120.2(5) . . ? F3 B1 F4 121.8(4) . . ? F3 B1 F1 118.2(4) . . ? F4 B1 F1 114.3(6) . . ? F3 B1 F2 105.4(5) . . ? F4 B1 F2 96.3(4) . . ? F1 B1 F2 91.7(6) . . ? C43 C41 C44 58.0(13) . . ? C43 C41 C43 58.1(11) . 2_667 ? C44 C41 C43 115.4(13) . 2_667 ? C43 C41 C45 120.1(11) . 2_667 ? C44 C41 C45 178.0(12) . 2_667 ? C43 C41 C45 62.6(10) 2_667 2_667 ? C44 C42 C45 121.8(17) . . ? C44 C42 C43 57.3(12) . . ? C45 C42 C43 64.9(13) . . ? C44 C43 C43 123.0(14) . 2_667 ? C44 C43 C41 61.0(6) . . ? C43 C43 C41 62.8(10) 2_667 . ? C44 C43 C42 60.2(6) . . ? C43 C43 C42 169(3) 2_667 . ? C41 C43 C42 121.2(12) . . ? C44 C43 C41 171(3) . 2_667 ? C43 C43 C41 59.1(10) 2_667 2_667 ? C41 C43 C41 121.9(11) . 2_667 ? C42 C43 C41 115.9(13) . 2_667 ? C44 C43 C45 116.4(8) . . ? C43 C43 C45 117.8(18) 2_667 . ? C41 C43 C45 172(3) . . ? C42 C43 C45 56.6(7) . . ? C41 C43 C45 59.3(11) 2_667 . ? C43 C44 C42 62.5(7) . . ? C43 C44 C41 61.0(6) . . ? C42 C44 C41 123.4(13) . . ? C42 C45 C41 116.5(19) . 2_667 ? C42 C45 C43 58.5(7) . . ? C41 C45 C43 58.0(14) 2_667 . ? _diffrn_measured_fraction_theta_max 0.984 _diffrn_reflns_theta_full 30.00 _diffrn_measured_fraction_theta_full 0.984 _refine_diff_density_max 4.147 _refine_diff_density_min -2.690 _refine_diff_density_rms 0.191 # Attachment '- [3]BF4.cif' data_sad2 _database_code_depnum_ccdc_archive 'CCDC 834829' #TrackingRef '- [3]BF4.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H38 B Cl F4 N2 Ni P2' _chemical_formula_weight 549.43 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ni Ni 0.3393 1.1124 '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 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 9.1013(5) _cell_length_b 30.6853(18) _cell_length_c 9.4384(6) _cell_angle_alpha 90.00 _cell_angle_beta 90.1290(10) _cell_angle_gamma 90.00 _cell_volume 2635.9(3) _cell_formula_units_Z 4 _cell_measurement_temperature 153(2) _cell_measurement_reflns_used 900 _cell_measurement_theta_min 1 _cell_measurement_theta_max 22.5 _exptl_crystal_description 'transparent prism' _exptl_crystal_colour 'intense brown-orange' _exptl_crystal_size_max 0.13 _exptl_crystal_size_mid 0.07 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.385 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1152 _exptl_absorpt_coefficient_mu 0.998 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8813 _exptl_absorpt_correction_T_max 0.9518 _exptl_absorpt_process_details ; Corrections were done with the SADABS program, utilizing the none merged raw data obtained from the integration process. Integration and final cell refinement were done with SAINT. SADABS reports ratio of Tmin/Tmax = 0.843461 ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 153(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'Omega and Phi scans' _diffrn_detector_area_resol_mean 80 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 19882 _diffrn_reflns_av_R_equivalents 0.0335 _diffrn_reflns_av_sigmaI/netI 0.0702 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -44 _diffrn_reflns_limit_k_max 45 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.33 _diffrn_reflns_theta_max 32.04 _reflns_number_total 6208 _reflns_number_gt 4472 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2(Bruker AXS, 2007)' _computing_cell_refinement 'APEX2(Bruker AXS, 2007)' _computing_data_reduction 'SAINT,SADABS (Bruker AXS, 2007 )' _computing_structure_solution ; SHELXS-97 , G. M. Sheldrick, Acta Cryst. (2008) A64, 112-122 ; _computing_structure_refinement ; SHELXL-97, G. M. Sheldrick, Acta Cryst. (2008) A64, 112-122 ; _computing_molecular_graphics ; ORTEP3,L.J. Farrugia, J. Appl. Cryst. (1997) 30, 565 ; _computing_publication_material ? _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^)+(0.0446P)^2^+0.0000P] 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 noref _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6208 _refine_ls_number_parameters 291 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0558 _refine_ls_R_factor_gt 0.0389 _refine_ls_wR_factor_ref 0.1032 _refine_ls_wR_factor_gt 0.0997 _refine_ls_goodness_of_fit_ref 0.953 _refine_ls_restrained_S_all 0.953 _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 Ni1 Ni 0.73000(3) 0.848650(8) 0.52498(3) 0.01767(7) Uani 1 1 d . . . Cl1 Cl 0.73311(7) 0.793800(17) 0.67304(6) 0.02815(12) Uani 1 1 d . . . P1 P 0.82420(6) 0.804928(17) 0.36039(6) 0.01988(11) Uani 1 1 d . . . P2 P 0.58206(7) 0.882996(18) 0.67501(6) 0.02175(12) Uani 1 1 d . . . N1 N 0.8698(2) 0.92192(6) 0.39566(19) 0.0196(3) Uani 1 1 d . . . N2 N 0.6502(2) 0.91250(6) 0.31188(19) 0.0204(3) Uani 1 1 d . . . H2N H 0.565(3) 0.9026(8) 0.282(3) 0.021(6) Uiso 1 1 d . . . C1 C 0.7481(2) 0.89652(6) 0.4064(2) 0.0185(4) Uani 1 1 d . . . C2 C 0.8484(2) 0.95413(6) 0.2925(2) 0.0197(4) Uani 1 1 d . . . C3 C 0.7074(2) 0.94829(6) 0.2391(2) 0.0195(4) Uani 1 1 d . . . C4 C 0.6494(3) 0.97497(7) 0.1345(2) 0.0247(4) Uani 1 1 d . . . H4 H 0.5528 0.9708 0.0986 0.030 Uiso 1 1 calc R . . C5 C 0.7393(3) 1.00805(7) 0.0848(3) 0.0287(5) Uani 1 1 d . . . H5 H 0.7038 1.0271 0.0130 0.034 Uiso 1 1 calc R . . C6 C 0.8824(3) 1.01406(8) 0.1385(3) 0.0316(5) Uani 1 1 d . . . H6 H 0.9412 1.0370 0.1017 0.038 Uiso 1 1 calc R . . C7 C 0.9396(3) 0.98742(7) 0.2436(3) 0.0279(5) Uani 1 1 d . . . H7 H 1.0358 0.9916 0.2805 0.034 Uiso 1 1 calc R . . C8 C 1.0013(3) 0.91729(8) 0.4818(3) 0.0282(5) Uani 1 1 d . . . H8A H 0.9875 0.8935 0.5498 0.042 Uiso 1 1 calc R . . H8B H 1.0197 0.9445 0.5331 0.042 Uiso 1 1 calc R . . H8C H 1.0853 0.9107 0.4206 0.042 Uiso 1 1 calc R . . C9 C 0.9785(3) 0.77070(8) 0.4121(3) 0.0318(5) Uani 1 1 d . . . H9A H 0.9473 0.7516 0.4911 0.038 Uiso 1 1 calc R . . H9B H 1.0048 0.7517 0.3313 0.038 Uiso 1 1 calc R . . C10 C 1.1152(3) 0.79603(10) 0.4583(4) 0.0466(7) Uani 1 1 d . . . H10A H 1.1474 0.8150 0.3808 0.070 Uiso 1 1 calc R . . H10B H 1.1940 0.7755 0.4822 0.070 Uiso 1 1 calc R . . H10C H 1.0918 0.8138 0.5415 0.070 Uiso 1 1 calc R . . C11 C 0.8776(3) 0.82982(7) 0.1917(2) 0.0248(4) Uani 1 1 d . . . H11A H 0.7916 0.8455 0.1528 0.030 Uiso 1 1 calc R . . H11B H 0.9550 0.8517 0.2109 0.030 Uiso 1 1 calc R . . C12 C 0.9342(3) 0.79848(9) 0.0783(3) 0.0372(6) Uani 1 1 d . . . H12A H 1.0285 0.7861 0.1088 0.056 Uiso 1 1 calc R . . H12B H 0.9476 0.8143 -0.0110 0.056 Uiso 1 1 calc R . . H12C H 0.8629 0.7749 0.0644 0.056 Uiso 1 1 calc R . . C13 C 0.6792(3) 0.76603(8) 0.3166(3) 0.0343(6) Uani 1 1 d . . . H13A H 0.7123 0.7475 0.2369 0.041 Uiso 1 1 calc R . . H13B H 0.6622 0.7468 0.3992 0.041 Uiso 1 1 calc R . . C14 C 0.5357(3) 0.78786(11) 0.2762(4) 0.0530(8) Uani 1 1 d . . . H14A H 0.5002 0.8053 0.3560 0.079 Uiso 1 1 calc R . . H14B H 0.4625 0.7656 0.2525 0.079 Uiso 1 1 calc R . . H14C H 0.5514 0.8068 0.1940 0.079 Uiso 1 1 calc R . . C15 C 0.6524(3) 0.88488(8) 0.8568(2) 0.0277(5) Uani 1 1 d . . . H15A H 0.5935 0.9060 0.9118 0.033 Uiso 1 1 calc R . . H15B H 0.6396 0.8559 0.9009 0.033 Uiso 1 1 calc R . . C16 C 0.8142(3) 0.89776(9) 0.8655(3) 0.0345(5) Uani 1 1 d . . . H16A H 0.8741 0.8756 0.8181 0.052 Uiso 1 1 calc R . . H16B H 0.8438 0.9000 0.9651 0.052 Uiso 1 1 calc R . . H16C H 0.8284 0.9260 0.8189 0.052 Uiso 1 1 calc R . . C17 C 0.5168(3) 0.93840(8) 0.6376(3) 0.0301(5) Uani 1 1 d . . . H17A H 0.4736 0.9387 0.5412 0.036 Uiso 1 1 calc R . . H17B H 0.4370 0.9453 0.7050 0.036 Uiso 1 1 calc R . . C18 C 0.6325(3) 0.97480(8) 0.6462(3) 0.0371(6) Uani 1 1 d . . . H18A H 0.6706 0.9767 0.7432 0.056 Uiso 1 1 calc R . . H18B H 0.5874 1.0026 0.6198 0.056 Uiso 1 1 calc R . . H18C H 0.7134 0.9683 0.5811 0.056 Uiso 1 1 calc R . . C19 C 0.4105(3) 0.85165(8) 0.6785(3) 0.0281(5) Uani 1 1 d . . . H19A H 0.3687 0.8516 0.5816 0.034 Uiso 1 1 calc R . . H19B H 0.4351 0.8211 0.7025 0.034 Uiso 1 1 calc R . . C20 C 0.2914(3) 0.86699(11) 0.7800(4) 0.0496(8) Uani 1 1 d . . . H20A H 0.3301 0.8670 0.8770 0.074 Uiso 1 1 calc R . . H20B H 0.2069 0.8473 0.7742 0.074 Uiso 1 1 calc R . . H20C H 0.2605 0.8965 0.7542 0.074 Uiso 1 1 calc R . . B1 B 0.2907(3) 0.89084(11) 0.1943(3) 0.0359(7) Uani 1 1 d . . . F1 F 0.40719(19) 0.90256(6) 0.10900(17) 0.0473(4) Uani 1 1 d . . . F2 F 0.3416(2) 0.88798(6) 0.33459(17) 0.0473(4) Uani 1 1 d . . . F3 F 0.2434(3) 0.84987(8) 0.1534(3) 0.0900(9) Uani 1 1 d . . . F4 F 0.1779(3) 0.91873(11) 0.1799(3) 0.1105(12) Uani 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 Ni1 0.02017(13) 0.01725(12) 0.01559(13) 0.00068(9) 0.00292(10) 0.00099(9) Cl1 0.0366(3) 0.0239(2) 0.0240(3) 0.00688(19) 0.0075(2) 0.0053(2) P1 0.0229(3) 0.0192(2) 0.0176(2) -0.00056(18) 0.0036(2) 0.0012(2) P2 0.0244(3) 0.0220(3) 0.0188(2) -0.00098(19) 0.0052(2) 0.0017(2) N1 0.0184(8) 0.0206(8) 0.0198(8) 0.0001(6) 0.0009(7) -0.0010(7) N2 0.0207(9) 0.0194(8) 0.0210(8) 0.0024(6) 0.0003(7) -0.0011(7) C1 0.0194(9) 0.0179(8) 0.0182(9) -0.0025(7) 0.0041(7) -0.0002(7) C2 0.0199(9) 0.0182(9) 0.0209(9) 0.0011(7) 0.0025(8) -0.0007(7) C3 0.0221(10) 0.0166(8) 0.0198(9) 0.0009(7) 0.0032(8) -0.0003(7) C4 0.0287(11) 0.0225(10) 0.0230(10) 0.0014(8) 0.0001(9) 0.0039(8) C5 0.0374(13) 0.0220(10) 0.0267(11) 0.0055(8) 0.0040(10) 0.0035(9) C6 0.0369(13) 0.0237(10) 0.0343(13) 0.0056(9) 0.0096(11) -0.0053(10) C7 0.0265(11) 0.0254(10) 0.0319(12) -0.0006(9) 0.0040(9) -0.0064(9) C8 0.0233(10) 0.0329(12) 0.0285(11) 0.0031(9) -0.0042(9) -0.0013(9) C9 0.0378(13) 0.0299(11) 0.0279(11) 0.0042(9) 0.0074(10) 0.0151(10) C10 0.0322(14) 0.0559(18) 0.0515(18) 0.0121(15) -0.0067(13) 0.0113(13) C11 0.0285(11) 0.0266(10) 0.0193(9) 0.0008(8) 0.0055(8) 0.0025(9) C12 0.0508(17) 0.0368(13) 0.0240(11) -0.0027(10) 0.0129(11) 0.0016(12) C13 0.0411(14) 0.0301(11) 0.0318(12) -0.0107(10) 0.0108(11) -0.0126(11) C14 0.0333(15) 0.066(2) 0.060(2) -0.0212(17) -0.0024(14) -0.0167(15) C15 0.0318(12) 0.0340(12) 0.0175(10) -0.0025(8) 0.0039(9) -0.0029(9) C16 0.0344(13) 0.0422(14) 0.0270(12) 0.0005(10) -0.0017(10) -0.0040(11) C17 0.0325(13) 0.0269(11) 0.0310(12) -0.0012(9) 0.0068(10) 0.0085(9) C18 0.0475(16) 0.0226(11) 0.0413(15) -0.0014(10) 0.0106(13) 0.0045(10) C19 0.0243(11) 0.0330(12) 0.0270(11) -0.0027(9) 0.0051(9) -0.0023(9) C20 0.0300(14) 0.069(2) 0.0493(18) -0.0210(16) 0.0151(13) -0.0112(14) B1 0.0238(13) 0.0518(17) 0.0322(15) 0.0147(13) 0.0029(11) -0.0019(12) F1 0.0331(9) 0.0763(12) 0.0325(8) -0.0009(8) 0.0092(7) -0.0176(8) F2 0.0366(9) 0.0767(12) 0.0285(8) 0.0094(8) 0.0009(7) -0.0080(9) F3 0.101(2) 0.1039(18) 0.0652(16) 0.0095(13) -0.0165(15) -0.0629(16) F4 0.092(2) 0.173(3) 0.0672(16) 0.0493(18) 0.0291(15) 0.086(2) _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 Ni1 C1 1.854(2) . ? Ni1 Cl1 2.1878(6) . ? Ni1 P2 2.2221(6) . ? Ni1 P1 2.2258(6) . ? P1 C9 1.820(2) . ? P1 C13 1.826(3) . ? P1 C11 1.833(2) . ? P2 C15 1.830(2) . ? P2 C19 1.834(2) . ? P2 C17 1.835(2) . ? N1 C1 1.359(3) . ? N1 C2 1.401(3) . ? N1 C8 1.452(3) . ? N2 C1 1.351(3) . ? N2 C3 1.397(3) . ? C2 C3 1.389(3) . ? C2 C7 1.395(3) . ? C3 C4 1.387(3) . ? C4 C5 1.387(3) . ? C5 C6 1.408(4) . ? C6 C7 1.386(4) . ? C9 C10 1.529(4) . ? C11 C12 1.529(3) . ? C13 C14 1.516(4) . ? C15 C16 1.527(4) . ? C17 C18 1.537(4) . ? C19 C20 1.523(4) . ? B1 F4 1.343(4) . ? B1 F1 1.380(3) . ? B1 F3 1.383(4) . ? B1 F2 1.405(4) . ? 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 C1 Ni1 Cl1 173.70(7) . . ? C1 Ni1 P2 93.64(6) . . ? Cl1 Ni1 P2 87.98(2) . . ? C1 Ni1 P1 91.23(6) . . ? Cl1 Ni1 P1 88.72(2) . . ? P2 Ni1 P1 164.92(3) . . ? C9 P1 C13 103.91(13) . . ? C9 P1 C11 105.52(11) . . ? C13 P1 C11 105.61(12) . . ? C9 P1 Ni1 117.31(9) . . ? C13 P1 Ni1 105.81(8) . . ? C11 P1 Ni1 117.29(7) . . ? C15 P2 C19 107.19(11) . . ? C15 P2 C17 105.29(12) . . ? C19 P2 C17 102.37(11) . . ? C15 P2 Ni1 113.65(8) . . ? C19 P2 Ni1 106.24(8) . . ? C17 P2 Ni1 120.87(8) . . ? C1 N1 C2 110.15(18) . . ? C1 N1 C8 124.99(18) . . ? C2 N1 C8 124.83(18) . . ? C1 N2 C3 111.35(18) . . ? N2 C1 N1 106.21(17) . . ? N2 C1 Ni1 128.81(16) . . ? N1 C1 Ni1 124.95(16) . . ? C3 C2 C7 121.6(2) . . ? C3 C2 N1 106.72(17) . . ? C7 C2 N1 131.7(2) . . ? C4 C3 C2 122.2(2) . . ? C4 C3 N2 132.3(2) . . ? C2 C3 N2 105.57(18) . . ? C5 C4 C3 116.7(2) . . ? C4 C5 C6 121.4(2) . . ? C7 C6 C5 121.7(2) . . ? C6 C7 C2 116.4(2) . . ? C10 C9 P1 114.19(18) . . ? C12 C11 P1 115.88(16) . . ? C14 C13 P1 112.95(19) . . ? C16 C15 P2 113.20(17) . . ? C18 C17 P2 116.20(18) . . ? C20 C19 P2 117.15(18) . . ? F4 B1 F1 111.3(2) . . ? F4 B1 F3 108.3(3) . . ? F1 B1 F3 108.3(3) . . ? F4 B1 F2 112.7(3) . . ? F1 B1 F2 108.3(2) . . ? F3 B1 F2 107.9(2) . . ? _diffrn_measured_fraction_theta_max 0.675 _diffrn_reflns_theta_full 32.04 _diffrn_measured_fraction_theta_full 0.675 _refine_diff_density_max 0.872 _refine_diff_density_min -0.642 _refine_diff_density_rms 0.064 # Attachment '- [3]PF6.cif' data_sad3 _database_code_depnum_ccdc_archive 'CCDC 834830' #TrackingRef '- [3]PF6.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H38 Cl F6 N2 Ni P3' _chemical_formula_weight 607.59 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' 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ni Ni 0.3393 1.1124 '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 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 11.6060(4) _cell_length_b 16.3414(6) _cell_length_c 15.5441(5) _cell_angle_alpha 90.00 _cell_angle_beta 104.3890(10) _cell_angle_gamma 90.00 _cell_volume 2855.59(17) _cell_formula_units_Z 4 _cell_measurement_temperature 153(2) _cell_measurement_reflns_used 900 _cell_measurement_theta_min 1 _cell_measurement_theta_max 22.5 _exptl_crystal_description 'transparent plate' _exptl_crystal_colour yellow-orange _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.413 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1264 _exptl_absorpt_coefficient_mu 0.992 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9073 _exptl_absorpt_correction_T_max 0.9614 _exptl_absorpt_process_details ; Corrections were done with the SADABS program, utilizing the none merged raw data obtained from the integration process. Integration and final cell refinement were done with SAINT. SADABS reports ratio of Tmin/Tmax = 0.841106 ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 153(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'Omega and Phi scans' _diffrn_detector_area_resol_mean 80 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 34098 _diffrn_reflns_av_R_equivalents 0.0227 _diffrn_reflns_av_sigmaI/netI 0.0209 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 1.84 _diffrn_reflns_theta_max 30.50 _reflns_number_total 8704 _reflns_number_gt 7215 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2(Bruker AXS, 2007)' _computing_cell_refinement 'APEX2(Bruker AXS, 2007)' _computing_data_reduction 'SAINT,SADABS (Bruker AXS, 2007 )' _computing_structure_solution ; SHELXS-97 , G. M. Sheldrick, Acta Cryst. (2008) A64, 112-122 ; _computing_structure_refinement ; SHELXL-97, G. M. Sheldrick, Acta Cryst. (2008) A64, 112-122 ; _computing_molecular_graphics ; ORTEP3,L.J. Farrugia, J. Appl. Cryst. (1997) 30, 565 ; _computing_publication_material ? _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^)+(0.0649P)^2^+3.3389P] 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 noref _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 8704 _refine_ls_number_parameters 305 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0539 _refine_ls_R_factor_gt 0.0433 _refine_ls_wR_factor_ref 0.1274 _refine_ls_wR_factor_gt 0.1190 _refine_ls_goodness_of_fit_ref 1.032 _refine_ls_restrained_S_all 1.032 _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 Ni1 Ni 0.76098(2) 0.648067(15) 0.340566(17) 0.01957(7) Uani 1 1 d . . . Cl1 Cl 0.80699(6) 0.53890(3) 0.27677(5) 0.03741(14) Uani 1 1 d . . . P1 P 0.94825(5) 0.68975(3) 0.35685(4) 0.02462(12) Uani 1 1 d . . . P2 P 0.57566(5) 0.60324(3) 0.32458(4) 0.02407(11) Uani 1 1 d . . . N1 N 0.69106(16) 0.81370(10) 0.36392(11) 0.0219(3) Uani 1 1 d . . . N2 N 0.73472(16) 0.74617(11) 0.48745(11) 0.0229(3) Uani 1 1 d . . . H2 H 0.7562 0.7061 0.5260 0.027 Uiso 1 1 calc R . . C1 C 0.72664(17) 0.73956(12) 0.39928(13) 0.0201(3) Uani 1 1 d . . . C2 C 0.67800(19) 0.86841(13) 0.42994(14) 0.0239(4) Uani 1 1 d . . . C3 C 0.70464(18) 0.82453(13) 0.50900(14) 0.0243(4) Uani 1 1 d . . . C4 C 0.6990(2) 0.86008(16) 0.58916(16) 0.0332(5) Uani 1 1 d . . . H4 H 0.7152 0.8296 0.6429 0.040 Uiso 1 1 calc R . . C5 C 0.6683(2) 0.94236(17) 0.58660(18) 0.0397(6) Uani 1 1 d . . . H5 H 0.6633 0.9690 0.6399 0.048 Uiso 1 1 calc R . . C6 C 0.6445(2) 0.98674(16) 0.5073(2) 0.0398(6) Uani 1 1 d . . . H6 H 0.6261 1.0433 0.5084 0.048 Uiso 1 1 calc R . . C7 C 0.6468(2) 0.95086(14) 0.42685(18) 0.0335(5) Uani 1 1 d . . . H7 H 0.6282 0.9808 0.3728 0.040 Uiso 1 1 calc R . . C8 C 0.6676(2) 0.83302(14) 0.26935(14) 0.0297(4) Uani 1 1 d . . . H8A H 0.6760 0.7833 0.2361 0.045 Uiso 1 1 calc R . . H8B H 0.7246 0.8743 0.2600 0.045 Uiso 1 1 calc R . . H8C H 0.5865 0.8544 0.2485 0.045 Uiso 1 1 calc R . . C9 C 0.9835(2) 0.79450(16) 0.39811(19) 0.0380(5) Uani 1 1 d . . . H9A H 0.9372 0.8328 0.3533 0.046 Uiso 1 1 calc R . . H9B H 0.9551 0.8011 0.4527 0.046 Uiso 1 1 calc R . . C10 C 1.1134(3) 0.8206(2) 0.4191(3) 0.0575(9) Uani 1 1 d . . . H10A H 1.1605 0.7852 0.4657 0.086 Uiso 1 1 calc R . . H10B H 1.1205 0.8775 0.4396 0.086 Uiso 1 1 calc R . . H10C H 1.1430 0.8158 0.3655 0.086 Uiso 1 1 calc R . . C11 C 1.0501(2) 0.62377(18) 0.43508(17) 0.0359(5) Uani 1 1 d . . . H11A H 1.0463 0.5678 0.4102 0.043 Uiso 1 1 calc R . . H11B H 1.1324 0.6442 0.4427 0.043 Uiso 1 1 calc R . . C12 C 1.0214(3) 0.6202(2) 0.52583(19) 0.0500(7) Uani 1 1 d . . . H12A H 1.0298 0.6749 0.5524 0.075 Uiso 1 1 calc R . . H12B H 1.0765 0.5825 0.5646 0.075 Uiso 1 1 calc R . . H12C H 0.9396 0.6009 0.5186 0.075 Uiso 1 1 calc R . . C13 C 1.0011(2) 0.68291(18) 0.25555(17) 0.0363(5) Uani 1 1 d . . . H13A H 1.0807 0.7086 0.2667 0.044 Uiso 1 1 calc R . . H13B H 1.0101 0.6245 0.2418 0.044 Uiso 1 1 calc R . . C14 C 0.9202(3) 0.7233(3) 0.1755(2) 0.0633(10) Uani 1 1 d . . . H14A H 0.8418 0.6972 0.1626 0.095 Uiso 1 1 calc R . . H14B H 0.9544 0.7174 0.1241 0.095 Uiso 1 1 calc R . . H14C H 0.9121 0.7815 0.1878 0.095 Uiso 1 1 calc R . . C15 C 0.4663(3) 0.6805(2) 0.3397(3) 0.0522(8) Uani 1 1 d . . . H15A H 0.5004 0.7096 0.3961 0.063 Uiso 1 1 calc R . . H15B H 0.4578 0.7212 0.2913 0.063 Uiso 1 1 calc R . . C16 C 0.3458(3) 0.6528(3) 0.3414(3) 0.0613(9) Uani 1 1 d . . . H16A H 0.3071 0.6280 0.2841 0.092 Uiso 1 1 calc R . . H16B H 0.2988 0.6997 0.3524 0.092 Uiso 1 1 calc R . . H16C H 0.3515 0.6123 0.3888 0.092 Uiso 1 1 calc R . . C17 C 0.5122(2) 0.5590(2) 0.21605(17) 0.0415(6) Uani 1 1 d . . . H17A H 0.5546 0.5074 0.2108 0.050 Uiso 1 1 calc R . . H17B H 0.4279 0.5452 0.2116 0.050 Uiso 1 1 calc R . . C18 C 0.5184(3) 0.6144(3) 0.1389(2) 0.0598(10) Uani 1 1 d . . . H18A H 0.4753 0.6653 0.1426 0.090 Uiso 1 1 calc R . . H18B H 0.4823 0.5866 0.0828 0.090 Uiso 1 1 calc R . . H18C H 0.6018 0.6270 0.1414 0.090 Uiso 1 1 calc R . . C19 C 0.5611(2) 0.52533(16) 0.40519(17) 0.0347(5) Uani 1 1 d . . . H19A H 0.5727 0.5519 0.4639 0.042 Uiso 1 1 calc R . . H19B H 0.4787 0.5040 0.3884 0.042 Uiso 1 1 calc R . . C20 C 0.6451(4) 0.4539(2) 0.4148(3) 0.0745(13) Uani 1 1 d . . . H20A H 0.6304 0.4240 0.3585 0.112 Uiso 1 1 calc R . . H20B H 0.6324 0.4174 0.4616 0.112 Uiso 1 1 calc R . . H20C H 0.7273 0.4739 0.4307 0.112 Uiso 1 1 calc R . . P3 P 0.21490(6) 0.38833(4) 0.30219(4) 0.03041(13) Uani 1 1 d . . . F1 F 0.13535(17) 0.31876(12) 0.33239(12) 0.0526(5) Uani 1 1 d . . . F2 F 0.1555(2) 0.37111(15) 0.20153(13) 0.0744(7) Uani 1 1 d . . . F3 F 0.2678(3) 0.40553(16) 0.40488(13) 0.0958(11) Uani 1 1 d . . . F4 F 0.2947(2) 0.45580(18) 0.27474(16) 0.0961(11) Uani 1 1 d . . . F5 F 0.1102(3) 0.45139(16) 0.2991(2) 0.0900(9) Uani 1 1 d . . . F6 F 0.3109(3) 0.3212(2) 0.3030(3) 0.1247(15) Uani 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 Ni1 0.02112(13) 0.01655(12) 0.02280(13) -0.00060(9) 0.00874(9) 0.00146(8) Cl1 0.0398(3) 0.0256(3) 0.0522(4) -0.0135(2) 0.0214(3) 0.0010(2) P1 0.0224(2) 0.0275(3) 0.0264(2) -0.0019(2) 0.0107(2) -0.00065(19) P2 0.0221(2) 0.0252(2) 0.0255(2) 0.00310(19) 0.00719(19) -0.00088(18) N1 0.0287(8) 0.0176(7) 0.0214(7) 0.0014(6) 0.0100(6) 0.0028(6) N2 0.0266(8) 0.0233(8) 0.0197(7) 0.0021(6) 0.0074(6) 0.0046(6) C1 0.0208(8) 0.0199(8) 0.0210(8) 0.0015(7) 0.0079(7) 0.0015(6) C2 0.0256(9) 0.0205(9) 0.0270(9) -0.0027(7) 0.0095(8) 0.0016(7) C3 0.0241(9) 0.0259(9) 0.0232(9) -0.0029(7) 0.0065(7) 0.0021(7) C4 0.0348(12) 0.0401(13) 0.0250(10) -0.0084(9) 0.0077(9) 0.0039(9) C5 0.0397(13) 0.0422(13) 0.0377(12) -0.0196(11) 0.0105(10) 0.0029(11) C6 0.0428(14) 0.0266(11) 0.0530(15) -0.0126(11) 0.0174(12) 0.0033(10) C7 0.0405(13) 0.0213(10) 0.0411(12) -0.0012(9) 0.0144(10) 0.0047(9) C8 0.0449(13) 0.0235(9) 0.0228(9) 0.0064(8) 0.0123(9) 0.0058(9) C9 0.0344(12) 0.0345(12) 0.0491(14) -0.0099(11) 0.0180(11) -0.0101(10) C10 0.0397(15) 0.063(2) 0.077(2) -0.0274(18) 0.0270(15) -0.0243(14) C11 0.0262(11) 0.0475(14) 0.0351(12) 0.0031(10) 0.0094(9) 0.0098(10) C12 0.0484(16) 0.070(2) 0.0335(13) 0.0109(13) 0.0136(12) 0.0214(15) C13 0.0317(12) 0.0488(14) 0.0338(12) -0.0023(10) 0.0182(10) -0.0031(10) C14 0.064(2) 0.097(3) 0.0371(15) 0.0196(17) 0.0264(15) 0.016(2) C15 0.0394(15) 0.0445(16) 0.081(2) 0.0112(15) 0.0302(15) 0.0105(12) C16 0.0402(16) 0.075(2) 0.071(2) 0.0029(19) 0.0179(16) 0.0025(15) C17 0.0364(13) 0.0569(16) 0.0294(11) 0.0007(11) 0.0050(10) -0.0128(12) C18 0.0508(18) 0.095(3) 0.0311(13) 0.0180(16) 0.0046(12) -0.0164(18) C19 0.0350(12) 0.0361(12) 0.0334(11) 0.0076(9) 0.0093(9) -0.0046(9) C20 0.098(3) 0.053(2) 0.090(3) 0.044(2) 0.056(3) 0.033(2) P3 0.0329(3) 0.0308(3) 0.0269(3) 0.0068(2) 0.0063(2) -0.0050(2) F1 0.0541(10) 0.0547(10) 0.0487(10) 0.0165(8) 0.0122(8) -0.0166(8) F2 0.1086(19) 0.0752(14) 0.0316(9) 0.0060(9) 0.0029(10) -0.0311(14) F3 0.144(2) 0.0837(16) 0.0359(10) 0.0128(10) -0.0222(12) -0.0648(17) F4 0.0762(15) 0.115(2) 0.0781(15) 0.0569(15) -0.0174(12) -0.0625(15) F5 0.112(2) 0.0654(15) 0.104(2) 0.0188(14) 0.0471(17) 0.0461(14) F6 0.107(2) 0.125(2) 0.176(3) 0.086(2) 0.100(2) 0.081(2) _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 Ni1 C1 1.8460(19) . ? Ni1 Cl1 2.1712(6) . ? Ni1 P2 2.2268(6) . ? Ni1 P1 2.2313(6) . ? P1 C11 1.823(3) . ? P1 C13 1.830(2) . ? P1 C9 1.838(3) . ? P2 C17 1.815(3) . ? P2 C19 1.823(2) . ? P2 C15 1.847(3) . ? N1 C1 1.352(2) . ? N1 C2 1.397(3) . ? N1 C8 1.462(3) . ? N2 C1 1.355(2) . ? N2 C3 1.390(3) . ? C2 C3 1.390(3) . ? C2 C7 1.393(3) . ? C3 C4 1.391(3) . ? C4 C5 1.389(4) . ? C5 C6 1.398(4) . ? C6 C7 1.387(4) . ? C9 C10 1.522(4) . ? C11 C12 1.529(4) . ? C13 C14 1.512(4) . ? C15 C16 1.476(5) . ? C17 C18 1.518(4) . ? C19 C20 1.504(4) . ? P3 F6 1.562(2) . ? P3 F4 1.5661(19) . ? P3 F2 1.570(2) . ? P3 F5 1.585(2) . ? P3 F3 1.587(2) . ? P3 F1 1.6064(17) . ? 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 C1 Ni1 Cl1 177.50(6) . . ? C1 Ni1 P2 90.03(6) . . ? Cl1 Ni1 P2 91.09(2) . . ? C1 Ni1 P1 91.18(6) . . ? Cl1 Ni1 P1 87.67(2) . . ? P2 Ni1 P1 178.57(2) . . ? C11 P1 C13 103.74(12) . . ? C11 P1 C9 105.47(14) . . ? C13 P1 C9 105.32(13) . . ? C11 P1 Ni1 110.30(9) . . ? C13 P1 Ni1 114.15(9) . . ? C9 P1 Ni1 116.74(8) . . ? C17 P2 C19 105.97(13) . . ? C17 P2 C15 104.93(17) . . ? C19 P2 C15 101.90(14) . . ? C17 P2 Ni1 113.10(9) . . ? C19 P2 Ni1 113.88(9) . . ? C15 P2 Ni1 115.86(11) . . ? C1 N1 C2 110.66(17) . . ? C1 N1 C8 124.35(17) . . ? C2 N1 C8 124.98(17) . . ? C1 N2 C3 111.03(17) . . ? N1 C1 N2 106.09(16) . . ? N1 C1 Ni1 127.33(14) . . ? N2 C1 Ni1 126.56(14) . . ? C3 C2 C7 121.9(2) . . ? C3 C2 N1 106.16(17) . . ? C7 C2 N1 131.9(2) . . ? C2 C3 N2 106.04(17) . . ? C2 C3 C4 121.8(2) . . ? N2 C3 C4 132.2(2) . . ? C5 C4 C3 116.6(2) . . ? C4 C5 C6 121.4(2) . . ? C7 C6 C5 122.1(2) . . ? C6 C7 C2 116.2(2) . . ? C10 C9 P1 117.3(2) . . ? C12 C11 P1 112.59(18) . . ? C14 C13 P1 114.2(2) . . ? C16 C15 P2 118.4(3) . . ? C18 C17 P2 114.1(2) . . ? C20 C19 P2 116.2(2) . . ? F6 P3 F4 91.55(18) . . ? F6 P3 F2 91.0(2) . . ? F4 P3 F2 89.87(13) . . ? F6 P3 F5 175.8(2) . . ? F4 P3 F5 92.02(17) . . ? F2 P3 F5 86.73(16) . . ? F6 P3 F3 91.1(2) . . ? F4 P3 F3 92.41(13) . . ? F2 P3 F3 176.85(16) . . ? F5 P3 F3 91.01(18) . . ? F6 P3 F1 87.80(15) . . ? F4 P3 F1 178.69(11) . . ? F2 P3 F1 91.29(11) . . ? F5 P3 F1 88.67(14) . . ? F3 P3 F1 86.46(11) . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 30.50 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 1.924 _refine_diff_density_min -0.820 _refine_diff_density_rms 0.083