# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full 'Dalton Trans.' _journal_coden_cambridge 0222 #TrackingRef '4950_web_deposit_cif_file_0_BrianSkelton_1302069886.cif' _audit_creation_date 09-04-02 _audit_update_record ? #============================================================================== # (Publishing Staff Use Only) _journal_date_recd_electronic ? _journal_date_to_coeditor ? _journal_date_from_coeditor ? _journal_date_accepted ? _journal_date_printers_first ? _journal_date_printers_final ? _journal_date_proofs_out ? _journal_date_proofs_in ? _journal_coeditor_name ? _journal_coeditor_code ? _journal_coeditor_notes ; ? ; _journal_techeditor_code ? _journal_techeditor_notes ; ? ; _journal_coden_ASTM ? _journal_year ? _journal_volume ? _journal_issue ? _journal_page_first ? _journal_page_last ? _journal_suppl_publ_number ? _journal_suppl_publ_pages ? #======================================================================= # 1. SUBMISSION DETAILS #---------------------- _publ_contact_author_name 'Skelton, B. W.' _publ_contact_author_address ; Department of Chemistry University of Western Australia 35 Stirling Highway Crawley Western Australia 6009 Australia ; _publ_contact_author_email bws@crystal.uwa.edu.au _publ_contact_author_fax (+61)_08_6488_1118 _publ_contact_author_phone (+61)_08_6488_7107 loop_ _publ_author_name _publ_author_footnote _publ_author_address 'D. H. Brown' . ;Chemistry, University of Western Australia, 35 Stirling Highway, Crawley, WA 6009, Australia. ; 'B. W. Skelton' '' '' _publ_section_references ; Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838. Johnson, C. K. (1976). ORTEPII. Report ORNL-5138. Oak Ridge National Laboratory, Tennessee, USA. Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838. Oxford Diffraction (2006). CrysAlis CCD. Oxford Diffraction Ltd, Abingdon, England. Oxford Diffraction (2006). CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England. Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122. ; data_dbb70c _database_code_depnum_ccdc_archive 'CCDC 820592' #TrackingRef '4950_web_deposit_cif_file_0_BrianSkelton_1302069886.cif' _audit_creation_date 2009-04-02T11:43:19-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_sum 'C28 H31 Br Cl2 F6 N5 Ni P' _chemical_formula_moiety 'C27 H29 Br N5 Ni, F6 P, C H2 Cl2' _chemical_formula_weight 792.07 #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _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 7.4959(6) _cell_length_b 10.4941(6) _cell_length_c 20.1343(12) _cell_angle_alpha 85.314(5) _cell_angle_beta 86.274(5) _cell_angle_gamma 76.779(6) _cell_volume 1534.94(18) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 5466 _cell_measurement_theta_min 3.532 _cell_measurement_theta_max 28.6197 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description needle _exptl_crystal_colour orange _exptl_crystal_size_max 0.74 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.014 _exptl_crystal_density_diffrn 1.714 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 800 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 2.226 _exptl_absorpt_correction_type Gaussian _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) (compiled Jun 10 2008,16:49:55) Analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by R.C. Clark & J.S. (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897) ; _exptl_absorpt_correction_T_min 0.557 _exptl_absorpt_correction_T_max 0.971 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_detector_area_resol_mean 10.4738 _diffrn_orient_matrix_ub_11 0.0161010811 _diffrn_orient_matrix_ub_12 -0.0685222542 _diffrn_orient_matrix_ub_13 -0.0034109349 _diffrn_orient_matrix_ub_21 -0.0941490146 _diffrn_orient_matrix_ub_22 0.0065161337 _diffrn_orient_matrix_ub_23 -0.0058568727 _diffrn_orient_matrix_ub_31 0.019179884 _diffrn_orient_matrix_ub_32 0.0105395811 _diffrn_orient_matrix_ub_33 -0.0347396007 _diffrn_reflns_av_R_equivalents 0.0506 _diffrn_reflns_av_unetI/netI 0.097 _diffrn_reflns_number 13531 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 3.53 _diffrn_reflns_theta_max 28.64 _diffrn_reflns_theta_full 26 _diffrn_measured_fraction_theta_full 0.991 _diffrn_measured_fraction_theta_max 0.847 _diffrn_measurement_device_type ; Oxford Diffraction Gemini diffractometer ; _diffrn_measurement_method '\w scans' _reflns_number_total 6682 _reflns_number_gt 4399 _reflns_threshold_expression I>2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection ; CrysAlis CCD, Oxford Diffraction Ltd., Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) (compiled Jun 10 2008,16:49:55) ; _computing_cell_refinement ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) (compiled Jun 10 2008,16:49:55) ; _computing_data_reduction ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) (compiled Jun 10 2008,16:49:55) ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'OrtepII (Johnson, C. K. (1976)' _computing_publication_material 'WinGX Farrugia, L. J. (1999)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 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^)+(0.0497P)^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 constr _refine_ls_extinction_method none _refine_ls_number_reflns 6682 _refine_ls_number_parameters 399 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.079 _refine_ls_R_factor_gt 0.0442 _refine_ls_wR_factor_ref 0.1012 _refine_ls_wR_factor_gt 0.0952 _refine_ls_goodness_of_fit_ref 0.927 _refine_ls_restrained_S_all 0.927 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.656 _refine_diff_density_min -0.762 _refine_diff_density_rms 0.103 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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' Br Br -0.2901 2.4595 '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' 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 0.36503(7) 0.67152(4) 0.24225(2) 0.01124(12) Uani 1 1 d . . . Br1 Br 0.37795(6) 0.67613(4) 0.127882(18) 0.02775(13) Uani 1 1 d . . . N11 N 0.7056(4) 0.7939(3) 0.21810(14) 0.0116(7) Uani 1 1 d . . . C12 C 0.5590(5) 0.7605(3) 0.25128(17) 0.0139(8) Uani 1 1 d . . . N13 N 0.5517(4) 0.8096(3) 0.31356(13) 0.0118(6) Uani 1 1 d . . . C13A C 0.6912(5) 0.8755(3) 0.31971(17) 0.0136(8) Uani 1 1 d . . . C14 C 0.7401(6) 0.9419(3) 0.36950(18) 0.0181(9) Uani 1 1 d . . . H14 H 0.6727 0.9504 0.4111 0.022 Uiso 1 1 calc R . . C15 C 0.8916(6) 0.9954(3) 0.35590(19) 0.0221(9) Uani 1 1 d . . . H15 H 0.9294 1.0411 0.3893 0.027 Uiso 1 1 calc R . . C16 C 0.9911(5) 0.9846(3) 0.29482(19) 0.0198(9) Uani 1 1 d . . . H16 H 1.0945 1.0229 0.2877 0.024 Uiso 1 1 calc R . . C17 C 0.9421(5) 0.9192(3) 0.24446(18) 0.0164(8) Uani 1 1 d . . . H17 H 1.0091 0.9118 0.2027 0.02 Uiso 1 1 calc R . . C17A C 0.7904(5) 0.8652(3) 0.25797(17) 0.0131(8) Uani 1 1 d . . . C1 C 0.7810(5) 0.7600(3) 0.15087(17) 0.0158(8) Uani 1 1 d . . . H1A H 0.7367 0.6837 0.1385 0.019 Uiso 1 1 calc R . . H1B H 0.9165 0.734 0.1516 0.019 Uiso 1 1 calc R . . C2 C 0.7274(5) 0.8727(3) 0.09823(16) 0.0156(8) Uani 1 1 d . . . H2A H 0.7607 0.9521 0.1124 0.019 Uiso 1 1 calc R . . H2B H 0.593 0.8927 0.0936 0.019 Uiso 1 1 calc R . . C3 C 0.8250(6) 0.8372(4) 0.03124(18) 0.0243(10) Uani 1 1 d . . . H3A H 0.7893 0.7587 0.017 0.029 Uiso 1 1 calc R . . H3B H 0.9591 0.8144 0.0366 0.029 Uiso 1 1 calc R . . C4 C 0.7797(6) 0.9484(4) -0.0230(2) 0.0336(11) Uani 1 1 d . . . H4A H 0.65 0.9631 -0.0329 0.05 Uiso 1 1 calc R . . H4B H 0.8563 0.9247 -0.0634 0.05 Uiso 1 1 calc R . . H4C H 0.8037 1.0287 -0.0074 0.05 Uiso 1 1 calc R . . N21 N 0.3186(4) 0.7061(3) 0.33192(13) 0.0106(6) Uani 1 1 d . . . C22 C 0.4176(5) 0.7768(3) 0.36017(17) 0.0125(8) Uani 1 1 d . . . C23 C 0.3856(5) 0.8066(3) 0.42584(17) 0.0155(8) Uani 1 1 d . . . H23 H 0.4567 0.856 0.4458 0.019 Uiso 1 1 calc R . . C24 C 0.2446(6) 0.7614(3) 0.46188(17) 0.0169(9) Uani 1 1 d . . . H24 H 0.2209 0.7788 0.5076 0.02 Uiso 1 1 calc R . . C25 C 0.1389(5) 0.6918(3) 0.43269(17) 0.0154(8) Uani 1 1 d . . . H25 H 0.042 0.6621 0.4573 0.018 Uiso 1 1 calc R . . C26 C 0.1784(5) 0.6669(3) 0.36670(17) 0.0118(8) Uani 1 1 d . . . N31 N 0.0669(4) 0.5121(3) 0.23384(13) 0.0116(6) Uani 1 1 d . . . C32 C 0.1660(5) 0.5832(3) 0.26144(16) 0.0120(8) Uani 1 1 d . . . N33 N 0.0897(4) 0.6011(3) 0.32572(13) 0.0105(6) Uani 1 1 d . . . C33A C -0.0607(5) 0.5424(3) 0.33768(17) 0.0134(8) Uani 1 1 d . . . C34 C -0.1854(5) 0.5365(3) 0.39203(18) 0.0155(8) Uani 1 1 d . . . H34 H -0.1782 0.577 0.432 0.019 Uiso 1 1 calc R . . C35 C -0.3198(5) 0.4688(3) 0.38440(18) 0.0179(9) Uani 1 1 d . . . H35 H -0.4065 0.462 0.4203 0.022 Uiso 1 1 calc R . . C36 C -0.3325(5) 0.4096(3) 0.32539(19) 0.0205(9) Uani 1 1 d . . . H36 H -0.4267 0.3634 0.3224 0.025 Uiso 1 1 calc R . . C37 C -0.2104(5) 0.4173(3) 0.27155(18) 0.0170(8) Uani 1 1 d . . . H37 H -0.2182 0.378 0.2313 0.02 Uiso 1 1 calc R . . C37A C -0.0752(5) 0.4856(3) 0.27942(17) 0.0136(8) Uani 1 1 d . . . C5 C 0.1006(5) 0.4614(3) 0.16714(16) 0.0138(8) Uani 1 1 d . . . H5A H 0.1311 0.5304 0.1348 0.017 Uiso 1 1 calc R . . H5B H -0.0128 0.4399 0.1532 0.017 Uiso 1 1 calc R . . C6 C 0.2563(6) 0.3395(3) 0.16542(18) 0.0230(10) Uani 1 1 d . . . H6A H 0.2883 0.3204 0.1182 0.028 Uiso 1 1 calc R . . H6B H 0.3651 0.3597 0.1839 0.028 Uiso 1 1 calc R . . C7 C 0.2191(6) 0.2198(4) 0.2021(2) 0.0290(10) Uani 1 1 d . . . H7A H 0.1192 0.1926 0.1811 0.035 Uiso 1 1 calc R . . H7B H 0.178 0.2389 0.2487 0.035 Uiso 1 1 calc R . . C8 C 0.3925(7) 0.1065(4) 0.2020(2) 0.0452(14) Uani 1 1 d . . . H8A H 0.4332 0.0875 0.1559 0.068 Uiso 1 1 calc R . . H8B H 0.3638 0.028 0.226 0.068 Uiso 1 1 calc R . . H8C H 0.4903 0.1323 0.224 0.068 Uiso 1 1 calc R . . P1 P 0.27108(14) 0.21912(9) 0.41420(5) 0.0163(2) Uani 1 1 d . . . F1 F 0.2820(3) 0.32157(19) 0.35161(11) 0.0236(5) Uani 1 1 d . . . F2 F 0.4860(3) 0.2032(2) 0.42380(11) 0.0264(5) Uani 1 1 d . . . F3 F 0.0564(3) 0.2360(2) 0.40528(12) 0.0301(6) Uani 1 1 d . . . F4 F 0.3154(3) 0.10145(19) 0.36595(10) 0.0236(5) Uani 1 1 d . . . F5 F 0.2265(4) 0.3386(2) 0.46203(12) 0.0429(7) Uani 1 1 d . . . F6 F 0.2606(4) 0.1161(2) 0.47681(11) 0.0425(7) Uani 1 1 d . . . Cl1 Cl 0.79831(18) 0.47138(11) 0.01871(6) 0.0396(3) Uani 1 1 d . . . Cl2 Cl 0.76799(18) 0.24233(11) 0.10726(6) 0.0418(3) Uani 1 1 d . . . C0 C 0.6571(7) 0.3679(5) 0.0497(2) 0.0393(12) Uani 1 1 d . . . H0A H 0.6178 0.3273 0.0121 0.047 Uiso 1 1 calc R . . H0B H 0.5458 0.4202 0.0719 0.047 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Ni1 0.0113(3) 0.0115(2) 0.0115(2) -0.00057(18) -0.00084(19) -0.00392(19) Br1 0.0327(3) 0.0425(3) 0.0152(2) -0.00312(17) 0.00094(18) -0.0233(2) N11 0.0127(18) 0.0087(14) 0.0137(15) 0.0043(12) -0.0038(13) -0.0035(13) C12 0.014(2) 0.0098(17) 0.0167(18) 0.0015(14) -0.0030(16) 0.0004(15) N13 0.0125(18) 0.0105(14) 0.0131(15) 0.0011(12) -0.0031(13) -0.0038(13) C13A 0.012(2) 0.0086(16) 0.0190(19) 0.0039(14) -0.0027(16) -0.0012(15) C14 0.019(2) 0.0154(18) 0.0193(19) 0.0002(16) -0.0042(17) -0.0017(17) C15 0.023(3) 0.0173(19) 0.028(2) -0.0022(17) -0.0108(19) -0.0063(18) C16 0.012(2) 0.0165(19) 0.032(2) 0.0044(17) -0.0052(18) -0.0053(17) C17 0.010(2) 0.0144(18) 0.023(2) 0.0042(16) 0.0007(16) -0.0016(16) C17A 0.011(2) 0.0087(16) 0.0186(19) 0.0026(15) -0.0051(16) -0.0009(15) C1 0.012(2) 0.0130(17) 0.0219(19) -0.0027(15) 0.0029(16) -0.0014(16) C2 0.013(2) 0.0182(18) 0.0145(18) -0.0005(15) 0.0004(16) -0.0018(16) C3 0.027(3) 0.025(2) 0.019(2) -0.0013(17) 0.0051(18) -0.0048(19) C4 0.027(3) 0.045(3) 0.021(2) 0.0104(19) 0.004(2) 0.001(2) N21 0.0082(17) 0.0099(14) 0.0133(14) -0.0006(12) -0.0010(13) -0.0007(13) C22 0.011(2) 0.0084(16) 0.0166(18) 0.0019(14) -0.0013(15) 0.0004(15) C23 0.013(2) 0.0132(17) 0.0203(19) -0.0018(15) -0.0058(16) -0.0015(16) C24 0.024(2) 0.0125(17) 0.0115(17) -0.0011(14) 0.0023(16) 0.0004(16) C25 0.014(2) 0.0158(18) 0.0155(18) 0.0007(15) -0.0024(16) -0.0018(16) C26 0.008(2) 0.0067(16) 0.0194(19) 0.0034(14) -0.0018(16) 0.0002(15) N31 0.0110(17) 0.0094(14) 0.0145(15) -0.0004(12) -0.0019(13) -0.0022(13) C32 0.013(2) 0.0077(16) 0.0142(18) 0.0005(14) -0.0023(15) -0.0007(15) N33 0.0089(17) 0.0103(14) 0.0119(14) -0.0002(12) 0.0005(12) -0.0018(12) C33A 0.012(2) 0.0082(16) 0.0191(19) 0.0039(14) -0.0021(16) -0.0010(15) C34 0.015(2) 0.0117(17) 0.0166(18) 0.0020(15) -0.0009(16) 0.0022(16) C35 0.013(2) 0.0181(19) 0.021(2) 0.0028(16) 0.0020(17) -0.0015(17) C36 0.012(2) 0.0169(19) 0.034(2) 0.0030(17) -0.0059(18) -0.0051(17) C37 0.014(2) 0.0149(18) 0.023(2) -0.0014(16) -0.0040(17) -0.0034(16) C37A 0.012(2) 0.0079(16) 0.0179(18) 0.0020(14) -0.0006(16) 0.0022(15) C5 0.015(2) 0.0146(17) 0.0138(18) -0.0003(14) -0.0054(15) -0.0060(16) C6 0.028(3) 0.022(2) 0.0164(19) -0.0085(16) 0.0006(18) 0.0014(18) C7 0.036(3) 0.024(2) 0.025(2) -0.0010(18) -0.002(2) -0.001(2) C8 0.056(4) 0.025(2) 0.041(3) 0.004(2) 0.012(3) 0.014(2) P1 0.0168(6) 0.0157(5) 0.0166(5) -0.0025(4) 0.0010(4) -0.0042(4) F1 0.0155(13) 0.0198(11) 0.0340(13) 0.0112(10) -0.0054(10) -0.0043(10) F2 0.0196(14) 0.0304(12) 0.0288(12) -0.0007(10) -0.0110(10) -0.0027(10) F3 0.0133(13) 0.0236(12) 0.0545(15) -0.0032(11) 0.0046(12) -0.0079(10) F4 0.0268(14) 0.0174(11) 0.0269(12) -0.0062(9) -0.0073(10) -0.0022(10) F5 0.0427(18) 0.0461(15) 0.0474(16) -0.0343(13) 0.0152(14) -0.0193(13) F6 0.059(2) 0.0518(16) 0.0210(12) 0.0138(11) -0.0034(13) -0.0276(15) Cl1 0.0432(8) 0.0411(6) 0.0354(6) -0.0016(5) -0.0010(6) -0.0123(6) Cl2 0.0441(8) 0.0340(6) 0.0467(7) -0.0017(5) -0.0034(6) -0.0078(6) C0 0.039(3) 0.050(3) 0.030(2) -0.006(2) 0.001(2) -0.011(2) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 N21 1.866(3) . ? Ni1 C12 1.924(4) . ? Ni1 C32 1.932(4) . ? Ni1 Br1 2.2955(6) . ? N11 C12 1.349(4) . ? N11 C17A 1.411(5) . ? N11 C1 1.472(4) . ? C12 N13 1.387(4) . ? N13 C13A 1.395(5) . ? N13 C22 1.412(4) . ? C13A C14 1.380(5) . ? C13A C17A 1.405(5) . ? C14 C15 1.381(5) . ? C14 H14 0.95 . ? C15 C16 1.395(5) . ? C15 H15 0.95 . ? C16 C17 1.382(5) . ? C16 H16 0.95 . ? C17 C17A 1.385(5) . ? C17 H17 0.95 . ? C1 C2 1.522(5) . ? C1 H1A 0.99 . ? C1 H1B 0.99 . ? C2 C3 1.524(5) . ? C2 H2A 0.99 . ? C2 H2B 0.99 . ? C3 C4 1.525(6) . ? C3 H3A 0.99 . ? C3 H3B 0.99 . ? C4 H4A 0.98 . ? C4 H4B 0.98 . ? C4 H4C 0.98 . ? N21 C22 1.342(5) . ? N21 C26 1.348(4) . ? C22 C23 1.377(5) . ? C23 C24 1.393(5) . ? C23 H23 0.95 . ? C24 C25 1.379(5) . ? C24 H24 0.95 . ? C25 C26 1.375(5) . ? C25 H25 0.95 . ? C26 N33 1.405(4) . ? N31 C32 1.339(4) . ? N31 C37A 1.422(4) . ? N31 C5 1.470(4) . ? C32 N33 1.390(4) . ? N33 C33A 1.403(4) . ? C33A C37A 1.380(5) . ? C33A C34 1.399(5) . ? C34 C35 1.381(5) . ? C34 H34 0.95 . ? C35 C36 1.403(5) . ? C35 H35 0.95 . ? C36 C37 1.382(5) . ? C36 H36 0.95 . ? C37 C37A 1.391(5) . ? C37 H37 0.95 . ? C5 C6 1.522(5) . ? C5 H5A 0.99 . ? C5 H5B 0.99 . ? C6 C7 1.478(5) . ? C6 H6A 0.99 . ? C6 H6B 0.99 . ? C7 C8 1.548(6) . ? C7 H7A 0.99 . ? C7 H7B 0.99 . ? C8 H8A 0.98 . ? C8 H8B 0.98 . ? C8 H8C 0.98 . ? P1 F4 1.595(2) . ? P1 F3 1.598(3) . ? P1 F1 1.599(2) . ? P1 F6 1.602(2) . ? P1 F2 1.604(3) . ? P1 F5 1.605(2) . ? Cl1 C0 1.738(5) . ? Cl2 C0 1.774(5) . ? C0 H0A 0.99 . ? C0 H0B 0.99 . ? 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 N21 Ni1 C12 81.72(13) . . ? N21 Ni1 C32 81.68(13) . . ? C12 Ni1 C32 163.08(14) . . ? N21 Ni1 Br1 166.68(9) . . ? C12 Ni1 Br1 97.64(10) . . ? C32 Ni1 Br1 99.27(10) . . ? C12 N11 C17A 110.8(3) . . ? C12 N11 C1 127.8(3) . . ? C17A N11 C1 121.4(3) . . ? N11 C12 N13 105.2(3) . . ? N11 C12 Ni1 142.5(3) . . ? N13 C12 Ni1 112.3(2) . . ? C12 N13 C13A 112.2(3) . . ? C12 N13 C22 116.0(3) . . ? C13A N13 C22 131.7(3) . . ? C14 C13A N13 134.4(3) . . ? C14 C13A C17A 121.1(3) . . ? N13 C13A C17A 104.5(3) . . ? C13A C14 C15 116.8(3) . . ? C13A C14 H14 121.6 . . ? C15 C14 H14 121.6 . . ? C14 C15 C16 122.3(4) . . ? C14 C15 H15 118.9 . . ? C16 C15 H15 118.9 . . ? C17 C16 C15 121.3(4) . . ? C17 C16 H16 119.4 . . ? C15 C16 H16 119.4 . . ? C16 C17 C17A 116.6(3) . . ? C16 C17 H17 121.7 . . ? C17A C17 H17 121.7 . . ? C17 C17A C13A 122.0(3) . . ? C17 C17A N11 130.7(3) . . ? C13A C17A N11 107.3(3) . . ? N11 C1 C2 112.8(3) . . ? N11 C1 H1A 109 . . ? C2 C1 H1A 109 . . ? N11 C1 H1B 109 . . ? C2 C1 H1B 109 . . ? H1A C1 H1B 107.8 . . ? C1 C2 C3 110.5(3) . . ? C1 C2 H2A 109.5 . . ? C3 C2 H2A 109.5 . . ? C1 C2 H2B 109.5 . . ? C3 C2 H2B 109.5 . . ? H2A C2 H2B 108.1 . . ? C2 C3 C4 112.6(3) . . ? C2 C3 H3A 109.1 . . ? C4 C3 H3A 109.1 . . ? C2 C3 H3B 109.1 . . ? C4 C3 H3B 109.1 . . ? H3A C3 H3B 107.8 . . ? C3 C4 H4A 109.5 . . ? C3 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? C3 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? C22 N21 C26 120.4(3) . . ? C22 N21 Ni1 119.7(2) . . ? C26 N21 Ni1 119.7(2) . . ? N21 C22 C23 121.6(3) . . ? N21 C22 N13 110.0(3) . . ? C23 C22 N13 128.4(3) . . ? C22 C23 C24 117.3(3) . . ? C22 C23 H23 121.3 . . ? C24 C23 H23 121.3 . . ? C25 C24 C23 121.4(3) . . ? C25 C24 H24 119.3 . . ? C23 C24 H24 119.3 . . ? C26 C25 C24 117.8(3) . . ? C26 C25 H25 121.1 . . ? C24 C25 H25 121.1 . . ? N21 C26 C25 121.4(3) . . ? N21 C26 N33 110.0(3) . . ? C25 C26 N33 128.7(3) . . ? C32 N31 C37A 110.6(3) . . ? C32 N31 C5 126.3(3) . . ? C37A N31 C5 123.1(3) . . ? N31 C32 N33 105.5(3) . . ? N31 C32 Ni1 142.5(2) . . ? N33 C32 Ni1 112.0(2) . . ? C32 N33 C33A 111.3(3) . . ? C32 N33 C26 116.4(3) . . ? C33A N33 C26 132.3(3) . . ? C37A C33A C34 121.2(3) . . ? C37A C33A N33 105.2(3) . . ? C34 C33A N33 133.6(3) . . ? C35 C34 C33A 116.4(3) . . ? C35 C34 H34 121.8 . . ? C33A C34 H34 121.8 . . ? C34 C35 C36 122.3(3) . . ? C34 C35 H35 118.9 . . ? C36 C35 H35 118.9 . . ? C37 C36 C35 121.1(4) . . ? C37 C36 H36 119.5 . . ? C35 C36 H36 119.5 . . ? C36 C37 C37A 116.5(3) . . ? C36 C37 H37 121.7 . . ? C37A C37 H37 121.7 . . ? C33A C37A C37 122.6(3) . . ? C33A C37A N31 107.4(3) . . ? C37 C37A N31 130.0(3) . . ? N31 C5 C6 112.2(3) . . ? N31 C5 H5A 109.2 . . ? C6 C5 H5A 109.2 . . ? N31 C5 H5B 109.2 . . ? C6 C5 H5B 109.2 . . ? H5A C5 H5B 107.9 . . ? C7 C6 C5 116.0(3) . . ? C7 C6 H6A 108.3 . . ? C5 C6 H6A 108.3 . . ? C7 C6 H6B 108.3 . . ? C5 C6 H6B 108.3 . . ? H6A C6 H6B 107.4 . . ? C6 C7 C8 111.1(4) . . ? C6 C7 H7A 109.4 . . ? C8 C7 H7A 109.4 . . ? C6 C7 H7B 109.4 . . ? C8 C7 H7B 109.4 . . ? H7A C7 H7B 108 . . ? C7 C8 H8A 109.5 . . ? C7 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C7 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? F4 P1 F3 90.21(13) . . ? F4 P1 F1 90.18(12) . . ? F3 P1 F1 90.24(13) . . ? F4 P1 F6 89.66(13) . . ? F3 P1 F6 89.85(14) . . ? F1 P1 F6 179.82(16) . . ? F4 P1 F2 90.39(12) . . ? F3 P1 F2 179.39(13) . . ? F1 P1 F2 89.89(12) . . ? F6 P1 F2 90.02(14) . . ? F4 P1 F5 179.37(14) . . ? F3 P1 F5 89.75(13) . . ? F1 P1 F5 89.18(13) . . ? F6 P1 F5 90.97(14) . . ? F2 P1 F5 89.65(13) . . ? Cl1 C0 Cl2 112.3(3) . . ? Cl1 C0 H0A 109.1 . . ? Cl2 C0 H0A 109.1 . . ? Cl1 C0 H0B 109.1 . . ? Cl2 C0 H0B 109.1 . . ? H0A C0 H0B 107.9 . . ? #===END # Attachment '4951_web_deposit_cif_file_1_BrianSkelton_1302069886.cif' data_dbb84e _database_code_depnum_ccdc_archive 'CCDC 820593' #TrackingRef '4951_web_deposit_cif_file_1_BrianSkelton_1302069886.cif' _audit_creation_date 2009-04-10T20:44:32-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_sum 'C27 H29 Cl F6 N5 Ni P' _chemical_formula_moiety 'C27 H29 Cl N5 Ni, F6 P' _chemical_formula_weight 662.68 #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _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 8.8351(5) _cell_length_b 9.5675(5) _cell_length_c 15.9437(10) _cell_angle_alpha 83.742(5) _cell_angle_beta 87.414(5) _cell_angle_gamma 82.567(5) _cell_volume 1327.77(13) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 4252 _cell_measurement_theta_min 3.3452 _cell_measurement_theta_max 32.4634 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description needle _exptl_crystal_colour yellow _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.03 _exptl_crystal_size_min 0.02 _exptl_crystal_density_diffrn 1.658 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 680 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.963 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) (compiled Jun 10 2008,16:49:55) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_absorpt_correction_T_min 0.91 _exptl_absorpt_correction_T_max 0.98 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_detector_area_resol_mean 10.4738 _diffrn_orient_matrix_ub_11 0.0212647689 _diffrn_orient_matrix_ub_12 -0.0679868687 _diffrn_orient_matrix_ub_13 0.0216648461 _diffrn_orient_matrix_ub_21 -0.051789614 _diffrn_orient_matrix_ub_22 -0.0288557202 _diffrn_orient_matrix_ub_23 -0.0239802138 _diffrn_orient_matrix_ub_31 0.0585506885 _diffrn_orient_matrix_ub_32 -0.0139761683 _diffrn_orient_matrix_ub_33 -0.030914809 _diffrn_reflns_av_R_equivalents 0.0516 _diffrn_reflns_av_unetI/netI 0.146 _diffrn_reflns_number 15104 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 3.35 _diffrn_reflns_theta_max 32.56 _diffrn_reflns_theta_full 30.5 _diffrn_measured_fraction_theta_full 0.993 _diffrn_measured_fraction_theta_max 0.896 _diffrn_measurement_device_type ; Oxford Diffraction Gemini diffractometer ; _diffrn_measurement_method '\w scans' _reflns_number_total 8661 _reflns_number_gt 4838 _reflns_threshold_expression I>2\s(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection ; CrysAlis CCD, Oxford Diffraction Ltd., Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) (compiled Jun 10 2008,16:49:55) ; _computing_cell_refinement ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) (compiled Jun 10 2008,16:49:55) ; _computing_data_reduction ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) (compiled Jun 10 2008,16:49:55) ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'OrtepII (Johnson, C. K. (1976)' _computing_publication_material 'WinGX Farrugia, L. J. (1999)' #----------------------------------------------------------------------------# # STRUCTURE SOLUTION #----------------------------------------------------------------------------# _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2\s(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0321P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_number_reflns 8661 _refine_ls_number_parameters 372 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1031 _refine_ls_R_factor_gt 0.0444 _refine_ls_wR_factor_ref 0.0866 _refine_ls_wR_factor_gt 0.0777 _refine_ls_goodness_of_fit_ref 0.834 _refine_ls_restrained_S_all 0.834 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.531 _refine_diff_density_min -0.45 _refine_diff_density_rms 0.096 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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' 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 0.23459(4) 0.35573(3) 0.706439(18) 0.01176(8) Uani 1 1 d . . . Cl1 Cl 0.27056(7) 0.38402(6) 0.57149(3) 0.01607(13) Uani 1 1 d . . . C1 C -0.0797(3) 0.3117(2) 0.57006(13) 0.0139(5) Uani 1 1 d . . . H1A H -0.0233 0.3949 0.5575 0.017 Uiso 1 1 calc R . . H1B H -0.1881 0.3427 0.5569 0.017 Uiso 1 1 calc R . . C2 C -0.0155(3) 0.1984(2) 0.51375(14) 0.0139(5) Uani 1 1 d . . . H2A H -0.0858 0.1253 0.5162 0.017 Uiso 1 1 calc R . . H2B H 0.0841 0.1519 0.5351 0.017 Uiso 1 1 calc R . . C3 C 0.0059(3) 0.2601(2) 0.42239(14) 0.0152(5) Uani 1 1 d . . . H3A H -0.0922 0.3121 0.4024 0.018 Uiso 1 1 calc R . . H3B H 0.0813 0.3287 0.4196 0.018 Uiso 1 1 calc R . . C4 C 0.0605(3) 0.1468(3) 0.36405(15) 0.0198(5) Uani 1 1 d . . . H4A H 0.1584 0.0958 0.383 0.03 Uiso 1 1 calc R . . H4B H 0.0733 0.1916 0.3063 0.03 Uiso 1 1 calc R . . H4C H -0.0152 0.0801 0.3652 0.03 Uiso 1 1 calc R . . C5 C 0.5490(3) 0.5519(2) 0.61643(14) 0.0128(5) Uani 1 1 d . . . H5A H 0.5301 0.4779 0.5807 0.015 Uiso 1 1 calc R . . H5B H 0.6561 0.5707 0.6058 0.015 Uiso 1 1 calc R . . C6 C 0.4437(3) 0.6860(2) 0.59121(14) 0.0149(5) Uani 1 1 d . . . H6A H 0.3415 0.6758 0.6174 0.018 Uiso 1 1 calc R . . H6B H 0.4333 0.6951 0.5292 0.018 Uiso 1 1 calc R . . C7 C 0.4934(3) 0.8221(2) 0.61521(15) 0.0177(5) Uani 1 1 d . . . H7A H 0.5936 0.8358 0.5875 0.021 Uiso 1 1 calc R . . H7B H 0.5056 0.814 0.677 0.021 Uiso 1 1 calc R . . C8 C 0.3779(3) 0.9502(2) 0.58928(16) 0.0214(6) Uani 1 1 d . . . H8A H 0.3554 0.9514 0.5296 0.032 Uiso 1 1 calc R . . H8B H 0.4203 1.037 0.5979 0.032 Uiso 1 1 calc R . . H8C H 0.2837 0.9445 0.6237 0.032 Uiso 1 1 calc R . . N11 N -0.0694(2) 0.26212(19) 0.66083(12) 0.0121(4) Uani 1 1 d . . . C12 C 0.0458(3) 0.2774(2) 0.70994(14) 0.0130(5) Uani 1 1 d . . . N13 N 0.0062(2) 0.22018(19) 0.79027(11) 0.0124(4) Uani 1 1 d . . . C13A C -0.1350(3) 0.1664(2) 0.79126(14) 0.0126(5) Uani 1 1 d . . . C14 C -0.2225(3) 0.0985(2) 0.85336(15) 0.0157(5) Uani 1 1 d . . . H14 H -0.1899 0.0786 0.9099 0.019 Uiso 1 1 calc R . . C15 C -0.3584(3) 0.0612(2) 0.82988(15) 0.0171(5) Uani 1 1 d . . . H15 H -0.4207 0.0144 0.8712 0.021 Uiso 1 1 calc R . . C16 C -0.4080(3) 0.0904(2) 0.74614(15) 0.0172(5) Uani 1 1 d . . . H16 H -0.5028 0.0636 0.7321 0.021 Uiso 1 1 calc R . . C17 C -0.3198(3) 0.1577(2) 0.68430(15) 0.0159(5) Uani 1 1 d . . . H17 H -0.3522 0.178 0.6278 0.019 Uiso 1 1 calc R . . C17A C -0.1825(3) 0.1941(2) 0.70806(14) 0.0142(5) Uani 1 1 d . . . N21 N 0.2212(2) 0.30243(19) 0.82150(11) 0.0117(4) Uani 1 1 d . . . C22 C 0.1034(3) 0.2342(2) 0.85472(14) 0.0131(5) Uani 1 1 d . . . C23 C 0.0901(3) 0.1907(2) 0.93961(14) 0.0147(5) Uani 1 1 d . . . H23 H 0.0053 0.1459 0.9627 0.018 Uiso 1 1 calc R . . C24 C 0.2056(3) 0.2150(2) 0.98991(14) 0.0159(5) Uani 1 1 d . . . H24 H 0.1992 0.1868 1.0488 0.019 Uiso 1 1 calc R . . C25 C 0.3314(3) 0.2797(2) 0.95678(14) 0.0142(5) Uani 1 1 d . . . H25 H 0.4121 0.2926 0.9914 0.017 Uiso 1 1 calc R . . C26 C 0.3332(3) 0.3241(2) 0.87149(14) 0.0135(5) Uani 1 1 d . . . N31 N 0.5281(2) 0.49822(19) 0.70620(11) 0.0117(4) Uani 1 1 d . . . C32 C 0.4133(3) 0.4285(2) 0.73859(14) 0.0128(5) Uani 1 1 d . . . N33 N 0.4412(2) 0.39600(19) 0.82354(11) 0.0122(4) Uani 1 1 d . . . C33A C 0.5782(3) 0.4411(2) 0.84430(14) 0.0127(5) Uani 1 1 d . . . C34 C 0.6603(3) 0.4280(2) 0.91747(14) 0.0159(5) Uani 1 1 d . . . H34 H 0.6239 0.3831 0.9692 0.019 Uiso 1 1 calc R . . C35 C 0.7972(3) 0.4834(2) 0.91152(15) 0.0174(5) Uani 1 1 d . . . H35 H 0.8568 0.4749 0.9604 0.021 Uiso 1 1 calc R . . C36 C 0.8519(3) 0.5515(2) 0.83646(15) 0.0186(5) Uani 1 1 d . . . H36 H 0.9459 0.59 0.8357 0.022 Uiso 1 1 calc R . . C37 C 0.7711(3) 0.5637(2) 0.76330(15) 0.0171(5) Uani 1 1 d . . . H37 H 0.8078 0.6088 0.7117 0.02 Uiso 1 1 calc R . . C37A C 0.6338(3) 0.5069(2) 0.76878(14) 0.0122(5) Uani 1 1 d . . . P1 P 0.23972(8) 0.80452(7) 0.85468(4) 0.01663(14) Uani 1 1 d . . . F1 F 0.2281(2) 0.74927(16) 0.76495(9) 0.0347(4) Uani 1 1 d . . . F2 F 0.20487(19) 0.65258(15) 0.89946(9) 0.0311(4) Uani 1 1 d . . . F3 F 0.2507(2) 0.85839(15) 0.94571(9) 0.0332(4) Uani 1 1 d . . . F4 F 0.27421(18) 0.95616(15) 0.81067(9) 0.0303(4) Uani 1 1 d . . . F5 F 0.41792(18) 0.75072(17) 0.85566(11) 0.0399(4) Uani 1 1 d . . . F6 F 0.06167(17) 0.85851(17) 0.85571(10) 0.0370(4) 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 0.01351(17) 0.01268(15) 0.00891(15) -0.00012(12) 0.00177(12) -0.00254(12) Cl1 0.0196(3) 0.0210(3) 0.0086(3) -0.0005(2) 0.0019(2) -0.0082(3) C1 0.0156(13) 0.0154(11) 0.0101(11) -0.0002(9) -0.0006(9) -0.0008(10) C2 0.0153(13) 0.0148(11) 0.0119(11) -0.0003(9) 0.0017(9) -0.0039(10) C3 0.0166(13) 0.0155(12) 0.0132(11) -0.0013(10) 0.0008(9) -0.0020(10) C4 0.0257(15) 0.0218(13) 0.0137(12) -0.0037(10) 0.0028(10) -0.0091(11) C5 0.0121(13) 0.0163(11) 0.0100(11) 0.0005(9) 0.0026(9) -0.0039(10) C6 0.0161(13) 0.0164(11) 0.0122(12) -0.0002(10) 0.0005(10) -0.0027(10) C7 0.0186(14) 0.0175(12) 0.0176(13) 0.0010(10) -0.0035(10) -0.0057(11) C8 0.0242(15) 0.0179(12) 0.0213(14) 0.0006(11) -0.0034(11) -0.0008(11) N11 0.0098(10) 0.0134(9) 0.0129(10) -0.0013(8) 0.0016(8) -0.0011(8) C12 0.0162(13) 0.0115(11) 0.0104(11) 0.0002(9) 0.0028(9) -0.0013(9) N13 0.0136(11) 0.0131(9) 0.0104(10) -0.0008(8) 0.0017(8) -0.0023(8) C13A 0.0122(13) 0.0100(11) 0.0157(12) -0.0024(9) 0.0007(9) -0.0012(9) C14 0.0186(14) 0.0144(11) 0.0136(12) -0.0004(10) 0.0015(10) -0.0015(10) C15 0.0159(14) 0.0144(11) 0.0207(13) -0.0019(10) 0.0054(10) -0.0029(10) C16 0.0152(13) 0.0150(12) 0.0223(13) -0.0073(10) 0.0020(10) -0.0020(10) C17 0.0184(14) 0.0133(11) 0.0159(12) -0.0045(10) 0.0017(10) 0.0000(10) C17A 0.0169(14) 0.0105(11) 0.0147(12) -0.0031(9) 0.0055(10) -0.0006(10) N21 0.0115(10) 0.0117(9) 0.0113(10) -0.0011(8) 0.0006(8) 0.0003(8) C22 0.0148(13) 0.0097(11) 0.0150(12) -0.0019(9) -0.0001(10) -0.0017(9) C23 0.0160(13) 0.0136(11) 0.0138(12) 0.0002(10) 0.0050(10) -0.0029(10) C24 0.0243(15) 0.0151(11) 0.0074(11) -0.0016(9) 0.0031(10) -0.0004(10) C25 0.0177(13) 0.0148(11) 0.0102(11) -0.0010(9) -0.0026(9) -0.0018(10) C26 0.0154(13) 0.0109(11) 0.0142(12) -0.0033(9) 0.0023(10) -0.0017(9) N31 0.0137(11) 0.0120(9) 0.0090(9) 0.0005(8) 0.0007(8) -0.0012(8) C32 0.0146(13) 0.0103(10) 0.0121(11) 0.0000(9) 0.0015(9) 0.0017(9) N33 0.0132(11) 0.0130(9) 0.0102(10) -0.0004(8) -0.0004(8) -0.0021(8) C33A 0.0139(13) 0.0098(10) 0.0143(12) -0.0037(9) 0.0021(9) 0.0002(9) C34 0.0212(14) 0.0140(11) 0.0117(12) -0.0008(9) 0.0021(10) -0.0004(10) C35 0.0177(14) 0.0175(12) 0.0173(13) -0.0045(10) -0.0024(10) -0.0007(10) C36 0.0176(14) 0.0194(12) 0.0203(13) -0.0046(10) 0.0002(10) -0.0060(11) C37 0.0200(14) 0.0145(12) 0.0168(13) -0.0028(10) 0.0030(10) -0.0029(10) C37A 0.0157(13) 0.0089(10) 0.0120(11) -0.0018(9) -0.0004(9) -0.0005(9) P1 0.0190(4) 0.0163(3) 0.0134(3) -0.0002(3) 0.0028(3) 0.0000(3) F1 0.0551(12) 0.0338(9) 0.0153(8) -0.0052(7) -0.0002(8) -0.0042(8) F2 0.0510(11) 0.0213(8) 0.0216(8) 0.0032(6) -0.0020(7) -0.0115(8) F3 0.0539(12) 0.0278(9) 0.0188(8) -0.0061(7) -0.0033(8) -0.0050(8) F4 0.0390(10) 0.0207(8) 0.0285(9) 0.0047(7) 0.0130(7) -0.0044(7) F5 0.0194(9) 0.0366(10) 0.0620(12) -0.0080(9) -0.0025(8) 0.0059(8) F6 0.0163(9) 0.0451(10) 0.0451(10) 0.0032(8) 0.0051(8) 0.0045(8) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Ni1 N21 1.8524(18) . ? Ni1 C12 1.911(2) . ? Ni1 C32 1.917(2) . ? Ni1 Cl1 2.1533(6) . ? C1 N11 1.476(3) . ? C1 C2 1.520(3) . ? C1 H1A 0.99 . ? C1 H1B 0.99 . ? C2 C3 1.524(3) . ? C2 H2A 0.99 . ? C2 H2B 0.99 . ? C3 C4 1.522(3) . ? C3 H3A 0.99 . ? C3 H3B 0.99 . ? C4 H4A 0.98 . ? C4 H4B 0.98 . ? C4 H4C 0.98 . ? C5 N31 1.479(3) . ? C5 C6 1.511(3) . ? C5 H5A 0.99 . ? C5 H5B 0.99 . ? C6 C7 1.519(3) . ? C6 H6A 0.99 . ? C6 H6B 0.99 . ? C7 C8 1.522(3) . ? C7 H7A 0.99 . ? C7 H7B 0.99 . ? C8 H8A 0.98 . ? C8 H8B 0.98 . ? C8 H8C 0.98 . ? N11 C12 1.344(3) . ? N11 C17A 1.408(3) . ? C12 N13 1.385(3) . ? N13 C22 1.396(3) . ? N13 C13A 1.408(3) . ? C13A C14 1.386(3) . ? C13A C17A 1.397(3) . ? C14 C15 1.375(3) . ? C14 H14 0.95 . ? C15 C16 1.412(3) . ? C15 H15 0.95 . ? C16 C17 1.384(3) . ? C16 H16 0.95 . ? C17 C17A 1.384(3) . ? C17 H17 0.95 . ? N21 C26 1.349(3) . ? N21 C22 1.357(3) . ? C22 C23 1.376(3) . ? C23 C24 1.384(3) . ? C23 H23 0.95 . ? C24 C25 1.397(3) . ? C24 H24 0.95 . ? C25 C26 1.380(3) . ? C25 H25 0.95 . ? C26 N33 1.399(3) . ? N31 C32 1.339(3) . ? N31 C37A 1.413(3) . ? C32 N33 1.382(3) . ? N33 C33A 1.401(3) . ? C33A C34 1.387(3) . ? C33A C37A 1.396(3) . ? C34 C35 1.377(3) . ? C34 H34 0.95 . ? C35 C36 1.396(3) . ? C35 H35 0.95 . ? C36 C37 1.381(3) . ? C36 H36 0.95 . ? C37 C37A 1.388(3) . ? C37 H37 0.95 . ? P1 F1 1.5902(15) . ? P1 F6 1.5908(17) . ? P1 F5 1.5922(17) . ? P1 F4 1.6010(15) . ? P1 F3 1.6032(15) . ? P1 F2 1.6085(15) . ? 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 N21 Ni1 C12 81.68(9) . . ? N21 Ni1 C32 81.55(9) . . ? C12 Ni1 C32 162.90(9) . . ? N21 Ni1 Cl1 170.68(6) . . ? C12 Ni1 Cl1 98.41(7) . . ? C32 Ni1 Cl1 98.68(7) . . ? N11 C1 C2 112.87(18) . . ? N11 C1 H1A 109 . . ? C2 C1 H1A 109 . . ? N11 C1 H1B 109 . . ? C2 C1 H1B 109 . . ? H1A C1 H1B 107.8 . . ? C1 C2 C3 111.84(18) . . ? C1 C2 H2A 109.2 . . ? C3 C2 H2A 109.2 . . ? C1 C2 H2B 109.2 . . ? C3 C2 H2B 109.2 . . ? H2A C2 H2B 107.9 . . ? C4 C3 C2 112.56(19) . . ? C4 C3 H3A 109.1 . . ? C2 C3 H3A 109.1 . . ? C4 C3 H3B 109.1 . . ? C2 C3 H3B 109.1 . . ? H3A C3 H3B 107.8 . . ? C3 C4 H4A 109.5 . . ? C3 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? C3 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? N31 C5 C6 112.80(19) . . ? N31 C5 H5A 109 . . ? C6 C5 H5A 109 . . ? N31 C5 H5B 109 . . ? C6 C5 H5B 109 . . ? H5A C5 H5B 107.8 . . ? C5 C6 C7 115.8(2) . . ? C5 C6 H6A 108.3 . . ? C7 C6 H6A 108.3 . . ? C5 C6 H6B 108.3 . . ? C7 C6 H6B 108.3 . . ? H6A C6 H6B 107.4 . . ? C6 C7 C8 111.7(2) . . ? C6 C7 H7A 109.3 . . ? C8 C7 H7A 109.3 . . ? C6 C7 H7B 109.3 . . ? C8 C7 H7B 109.3 . . ? H7A C7 H7B 107.9 . . ? C7 C8 H8A 109.5 . . ? C7 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C7 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C12 N11 C17A 110.79(18) . . ? C12 N11 C1 125.37(19) . . ? C17A N11 C1 123.83(19) . . ? N11 C12 N13 105.86(19) . . ? N11 C12 Ni1 141.62(17) . . ? N13 C12 Ni1 112.46(15) . . ? C12 N13 C22 116.63(19) . . ? C12 N13 C13A 111.16(18) . . ? C22 N13 C13A 132.02(19) . . ? C14 C13A C17A 121.2(2) . . ? C14 C13A N13 134.1(2) . . ? C17A C13A N13 104.76(19) . . ? C15 C14 C13A 117.3(2) . . ? C15 C14 H14 121.4 . . ? C13A C14 H14 121.4 . . ? C14 C15 C16 121.8(2) . . ? C14 C15 H15 119.1 . . ? C16 C15 H15 119.1 . . ? C17 C16 C15 120.6(2) . . ? C17 C16 H16 119.7 . . ? C15 C16 H16 119.7 . . ? C16 C17 C17A 117.4(2) . . ? C16 C17 H17 121.3 . . ? C17A C17 H17 121.3 . . ? C17 C17A C13A 121.7(2) . . ? C17 C17A N11 130.9(2) . . ? C13A C17A N11 107.4(2) . . ? C26 N21 C22 119.96(19) . . ? C26 N21 Ni1 119.91(16) . . ? C22 N21 Ni1 120.03(15) . . ? N21 C22 C23 122.0(2) . . ? N21 C22 N13 109.10(19) . . ? C23 C22 N13 128.9(2) . . ? C22 C23 C24 117.0(2) . . ? C22 C23 H23 121.5 . . ? C24 C23 H23 121.5 . . ? C23 C24 C25 122.1(2) . . ? C23 C24 H24 119 . . ? C25 C24 H24 119 . . ? C26 C25 C24 117.1(2) . . ? C26 C25 H25 121.5 . . ? C24 C25 H25 121.5 . . ? N21 C26 C25 121.8(2) . . ? N21 C26 N33 109.63(19) . . ? C25 C26 N33 128.6(2) . . ? C32 N31 C37A 110.75(18) . . ? C32 N31 C5 125.48(18) . . ? C37A N31 C5 123.67(18) . . ? N31 C32 N33 105.81(19) . . ? N31 C32 Ni1 141.65(17) . . ? N33 C32 Ni1 112.48(16) . . ? C32 N33 C26 116.19(19) . . ? C32 N33 C33A 111.44(18) . . ? C26 N33 C33A 132.36(19) . . ? C34 C33A C37A 120.8(2) . . ? C34 C33A N33 134.3(2) . . ? C37A C33A N33 104.86(19) . . ? C35 C34 C33A 116.8(2) . . ? C35 C34 H34 121.6 . . ? C33A C34 H34 121.6 . . ? C34 C35 C36 122.6(2) . . ? C34 C35 H35 118.7 . . ? C36 C35 H35 118.7 . . ? C37 C36 C35 120.9(2) . . ? C37 C36 H36 119.6 . . ? C35 C36 H36 119.6 . . ? C36 C37 C37A 116.8(2) . . ? C36 C37 H37 121.6 . . ? C37A C37 H37 121.6 . . ? C37 C37A C33A 122.2(2) . . ? C37 C37A N31 130.7(2) . . ? C33A C37A N31 107.10(19) . . ? F1 P1 F6 90.33(9) . . ? F1 P1 F5 90.79(10) . . ? F6 P1 F5 178.83(10) . . ? F1 P1 F4 90.82(8) . . ? F6 P1 F4 90.07(9) . . ? F5 P1 F4 90.24(9) . . ? F1 P1 F3 179.28(9) . . ? F6 P1 F3 89.59(9) . . ? F5 P1 F3 89.29(10) . . ? F4 P1 F3 89.90(8) . . ? F1 P1 F2 89.53(8) . . ? F6 P1 F2 89.84(9) . . ? F5 P1 F2 89.84(9) . . ? F4 P1 F2 179.63(9) . . ? F3 P1 F2 89.75(8) . . ? #===END # Attachment '4952_web_deposit_cif_file_2_BrianSkelton_1302069886.cif' data_dbb70 _database_code_depnum_ccdc_archive 'CCDC 820594' #TrackingRef '4952_web_deposit_cif_file_2_BrianSkelton_1302069886.cif' _audit_creation_date 2009-05-04T14:27:06-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_sum 'C27 H35 Cl2 N5 Ni O3' _chemical_formula_moiety 'C27 H29 Cl1 N5 Ni, Cl, 3(H2 O)' _chemical_formula_weight 607.21 #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21/n 1' _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 23.7588(9) _cell_length_b 4.9770(2) _cell_length_c 26.5360(10) _cell_angle_alpha 90 _cell_angle_beta 115.587(5) _cell_angle_gamma 90 _cell_volume 2830.09(22) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 4861 _cell_measurement_theta_min 3.3076 _cell_measurement_theta_max 67.0903 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description rod _exptl_crystal_colour yellow _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.1 _exptl_crystal_size_min 0.06 _exptl_crystal_density_diffrn 1.425 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1272 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 3.034 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) (compiled Jun 10 2008,16:49:55) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_absorpt_correction_T_min 0.69 _exptl_absorpt_correction_T_max 0.83 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_monochromator graphite _diffrn_detector_area_resol_mean 10.4738 _diffrn_orient_matrix_ub_11 0.0288067197 _diffrn_orient_matrix_ub_12 -0.1850062625 _diffrn_orient_matrix_ub_13 -0.0292575701 _diffrn_orient_matrix_ub_21 -0.063202272 _diffrn_orient_matrix_ub_22 -0.0112281107 _diffrn_orient_matrix_ub_23 -0.0521243386 _diffrn_orient_matrix_ub_31 0.0186824752 _diffrn_orient_matrix_ub_32 0.2481069313 _diffrn_orient_matrix_ub_33 -0.0240245802 _diffrn_measurement_device_type ; Goniometer Xcalibur, detector: Ruby (Gemini ultra Cu) ; _diffrn_measurement_method '\w scans' _diffrn_reflns_av_R_equivalents 0.0329 _diffrn_reflns_av_unetI/netI 0.0417 _diffrn_reflns_number 11979 _diffrn_reflns_limit_h_min -28 _diffrn_reflns_limit_h_max 27 _diffrn_reflns_limit_k_min -4 _diffrn_reflns_limit_k_max 5 _diffrn_reflns_limit_l_min -31 _diffrn_reflns_limit_l_max 30 _diffrn_reflns_theta_min 3.31 _diffrn_reflns_theta_max 67.21 _diffrn_reflns_theta_full 66.50 _diffrn_measured_fraction_theta_full 0.96 _diffrn_measured_fraction_theta_max 0.947 _reflns_number_total 4776 _reflns_number_gt 3649 _reflns_threshold_expression I>2\s(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection ; CrysAlis CCD, Oxford Diffraction Ltd., Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) (compiled Jun 10 2008,16:49:55) ; _computing_cell_refinement ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) (compiled Jun 10 2008,16:49:55) ; _computing_data_reduction ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) (compiled Jun 10 2008,16:49:55) ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'OrtepII (Johnson, C. K. (1976)' _computing_publication_material 'WinGX Farrugia, L. J. (1999)' #----------------------------------------------------------------------------# # STRUCTURE SOLUTION #----------------------------------------------------------------------------# _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2\s(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1203P)^2^+0.1186P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_number_reflns 4776 _refine_ls_number_parameters 360 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0716 _refine_ls_R_factor_gt 0.0536 _refine_ls_wR_factor_ref 0.1749 _refine_ls_wR_factor_gt 0.1613 _refine_ls_goodness_of_fit_ref 1.06 _refine_ls_restrained_S_all 1.06 _refine_ls_shift/su_max 0.005 _refine_ls_shift/su_mean 0 _refine_diff_density_max 1.35 _refine_diff_density_min -0.723 _refine_diff_density_rms 0.092 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ni Ni -3.0029 0.5091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Ni1 Ni 0.71713(3) 0.66252(12) 0.46032(2) 0.0216(2) Uani 1 1 d . . . C1 C 0.60172(17) 0.9142(7) 0.32207(15) 0.0230(8) Uani 1 1 d . . . H1A H 0.5992 0.7264 0.3332 0.028 Uiso 1 1 calc R . . H1B H 0.592 0.9138 0.2818 0.028 Uiso 1 1 calc R . . C2 C 0.55312(17) 1.0809(7) 0.33055(16) 0.0260(8) Uani 1 1 d . . . H2A H 0.5532 1.2657 0.3168 0.031 Uiso 1 1 calc R . . H2B H 0.564 1.0917 0.371 0.031 Uiso 1 1 calc R . . C3 C 0.48833(18) 0.9604(8) 0.29990(16) 0.0268(8) Uani 1 1 d . . . H3A H 0.4889 0.7732 0.3127 0.032 Uiso 1 1 calc R . . H3B H 0.477 0.9555 0.2594 0.032 Uiso 1 1 calc R . . C4 C 0.43901(19) 1.1198(8) 0.30959(18) 0.0327(9) Uani 1 1 d . . . H4A H 0.4379 1.3047 0.2965 0.049 Uiso 1 1 calc R . . H4B H 0.4494 1.121 0.3496 0.049 Uiso 1 1 calc R . . H4C H 0.3981 1.036 0.2889 0.049 Uiso 1 1 calc R . . C5 C 0.67404(19) 0.1280(8) 0.53553(17) 0.0289(9) Uani 1 1 d . . . H5A H 0.6766 -0.0631 0.5466 0.035 Uiso 1 1 calc R . . H5B H 0.6492 0.1383 0.4945 0.035 Uiso 1 1 calc R . . C6 C 0.64136(19) 0.2865(7) 0.56397(17) 0.0281(9) Uani 1 1 d . . . H6A H 0.6373 0.4764 0.5518 0.034 Uiso 1 1 calc R . . H6B H 0.6668 0.2817 0.6049 0.034 Uiso 1 1 calc R . . C7 C 0.5767(2) 0.1710(8) 0.5499(2) 0.0368(10) Uani 1 1 d . . . H7A H 0.5812 -0.0142 0.5647 0.044 Uiso 1 1 calc R . . H7B H 0.5526 0.1617 0.5088 0.044 Uiso 1 1 calc R . . C8 C 0.5407(2) 0.3404(9) 0.5742(2) 0.0436(11) Uani 1 1 d . . . H8A H 0.5339 0.5208 0.5578 0.065 Uiso 1 1 calc R . . H8B H 0.5648 0.3534 0.6148 0.065 Uiso 1 1 calc R . . H8C H 0.5004 0.2557 0.5656 0.065 Uiso 1 1 calc R . . N11 N 0.66576(14) 1.0125(6) 0.35399(12) 0.0215(6) Uani 1 1 d . . . C12 C 0.70726(17) 0.9198(7) 0.40310(15) 0.0219(8) Uani 1 1 d . . . N13 N 0.76187(14) 1.0601(6) 0.41513(12) 0.0214(6) Uani 1 1 d . . . C13A C 0.75371(17) 1.2488(7) 0.37356(15) 0.0212(7) Uani 1 1 d . . . C14 C 0.79285(17) 1.4368(7) 0.36600(16) 0.0239(8) Uani 1 1 d . . . H14 H 0.8351 1.4583 0.3925 0.029 Uiso 1 1 calc R . . C15 C 0.76692(18) 1.5915(7) 0.31765(16) 0.0257(8) Uani 1 1 d . . . H15 H 0.7919 1.7244 0.3113 0.031 Uiso 1 1 calc R . . C16 C 0.70501(18) 1.5565(7) 0.27802(16) 0.0254(8) Uani 1 1 d . . . H16 H 0.6892 1.664 0.2452 0.03 Uiso 1 1 calc R . . C17 C 0.66635(18) 1.3683(7) 0.28562(15) 0.0241(8) Uani 1 1 d . . . H17 H 0.6244 1.3441 0.2588 0.029 Uiso 1 1 calc R . . C17A C 0.69202(17) 1.2166(7) 0.33436(15) 0.0201(7) Uani 1 1 d . . . N21 N 0.79957(14) 0.7732(6) 0.48755(13) 0.0223(7) Uani 1 1 d . . . C22 C 0.81464(16) 0.9759(7) 0.46232(14) 0.0206(7) Uani 1 1 d . . . C23 C 0.87532(18) 1.0721(8) 0.48230(16) 0.0260(8) Uani 1 1 d . . . H23 H 0.8859 1.2157 0.4644 0.031 Uiso 1 1 calc R . . C24 C 0.91980(18) 0.9493(8) 0.52959(16) 0.0277(8) Uani 1 1 d . . . H24 H 0.9619 1.0088 0.544 0.033 Uiso 1 1 calc R . . C25 C 0.90468(18) 0.7414(8) 0.55657(16) 0.0265(8) Uani 1 1 d . . . H25 H 0.9353 0.6588 0.5891 0.032 Uiso 1 1 calc R . . C26 C 0.84334(18) 0.6610(7) 0.53391(15) 0.0242(8) Uani 1 1 d . . . N31 N 0.73708(15) 0.2306(6) 0.55034(13) 0.0260(7) Uani 1 1 d . . . C32 C 0.75183(18) 0.4290(7) 0.52367(16) 0.0242(8) Uani 1 1 d . . . N33 N 0.81605(15) 0.4636(6) 0.55393(13) 0.0250(7) Uani 1 1 d . . . C33A C 0.84090(19) 0.2869(7) 0.59965(16) 0.0271(8) Uani 1 1 d . . . C34 C 0.9004(2) 0.2435(8) 0.64072(17) 0.0315(9) Uani 1 1 d . . . H34 H 0.9351 0.3464 0.6429 0.038 Uiso 1 1 calc R . . C35 C 0.9067(2) 0.0396(8) 0.67885(17) 0.0376(10) Uani 1 1 d . . . H35 H 0.9469 0.0008 0.7076 0.045 Uiso 1 1 calc R . . C36 C 0.8557(2) -0.1091(8) 0.67610(18) 0.0388(10) Uani 1 1 d . . . H36 H 0.8621 -0.2457 0.7031 0.047 Uiso 1 1 calc R . . C37 C 0.7956(2) -0.0629(8) 0.63491(18) 0.0346(10) Uani 1 1 d . . . H37 H 0.7607 -0.1635 0.633 0.041 Uiso 1 1 calc R . . C37A C 0.78962(19) 0.1400(8) 0.59671(17) 0.0291(9) Uani 1 1 d . . . Cl1 Cl 0.62072(4) 0.57342(18) 0.43470(4) 0.0276(2) Uani 1 1 d . . . Cl2 Cl 0.91935(9) 0.9924(6) 0.36734(9) 0.0377(6) Uani 0.669(7) 1 d P . . O2 O 0.9122(9) 0.913(4) 0.3559(9) 0.073(7) Uiso 0.331(7) 1 d P . . Cl3 Cl 1.0335(5) 0.516(2) 0.6828(4) 0.073(2) Uani 0.331(7) 1 d P . . O3 O 1.0464(4) 0.539(2) 0.6702(3) 0.0424(18) Uani 0.669(7) 1 d P . . O4 O 0.95267(15) 0.5034(7) 0.44645(13) 0.0483(8) Uani 1 1 d . . . O5 O 0.7626(4) -0.004(2) 0.7796(3) 0.194(4) 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 0.0220(4) 0.0222(4) 0.0198(4) -0.0009(2) 0.0083(3) -0.0001(2) C1 0.0220(19) 0.0232(19) 0.0197(18) -0.0061(14) 0.0050(15) -0.0037(15) C2 0.023(2) 0.0263(19) 0.026(2) -0.0038(15) 0.0077(16) -0.0004(15) C3 0.027(2) 0.027(2) 0.027(2) -0.0051(15) 0.0116(17) -0.0037(16) C4 0.027(2) 0.037(2) 0.037(2) -0.0055(18) 0.0160(19) -0.0030(17) C5 0.033(2) 0.0271(19) 0.030(2) -0.0005(15) 0.0161(18) -0.0018(16) C6 0.037(2) 0.0240(19) 0.027(2) -0.0038(15) 0.0179(18) -0.0038(17) C7 0.042(3) 0.029(2) 0.049(3) -0.0037(18) 0.029(2) -0.0063(18) C8 0.045(3) 0.039(2) 0.060(3) -0.006(2) 0.035(2) -0.004(2) N11 0.0204(16) 0.0226(15) 0.0204(15) -0.0023(12) 0.0078(13) 0.0003(12) C12 0.0201(19) 0.0232(18) 0.0216(18) -0.0066(14) 0.0084(15) -0.0009(14) N13 0.0200(16) 0.0246(15) 0.0187(15) 0.0001(12) 0.0075(13) 0.0002(12) C13A 0.0219(19) 0.0225(17) 0.0184(18) -0.0020(13) 0.0079(15) 0.0033(14) C14 0.0205(19) 0.0269(19) 0.0250(19) -0.0041(15) 0.0103(16) -0.0030(15) C15 0.027(2) 0.0250(19) 0.028(2) 0.0001(15) 0.0146(17) 0.0015(16) C16 0.030(2) 0.0253(19) 0.0209(19) 0.0004(14) 0.0112(16) 0.0040(16) C17 0.0234(19) 0.0261(19) 0.0217(19) -0.0007(14) 0.0088(16) 0.0019(15) C17A 0.0207(18) 0.0220(18) 0.0195(18) -0.0017(13) 0.0103(15) 0.0015(14) N21 0.0230(16) 0.0221(15) 0.0207(16) -0.0021(12) 0.0084(13) 0.0021(13) C22 0.0197(18) 0.0250(18) 0.0168(17) -0.0025(13) 0.0077(15) 0.0027(14) C23 0.024(2) 0.030(2) 0.0225(19) -0.0005(15) 0.0088(16) 0.0011(16) C24 0.021(2) 0.036(2) 0.024(2) -0.0022(16) 0.0072(16) 0.0004(16) C25 0.024(2) 0.032(2) 0.0196(19) -0.0004(15) 0.0054(16) 0.0043(16) C26 0.028(2) 0.0268(19) 0.0182(18) -0.0015(14) 0.0104(16) 0.0044(16) N31 0.0325(18) 0.0225(16) 0.0254(17) 0.0005(12) 0.0148(15) 0.0018(13) C32 0.029(2) 0.0226(18) 0.0246(19) -0.0032(14) 0.0145(17) 0.0005(15) N33 0.0250(17) 0.0238(16) 0.0250(17) 0.0000(12) 0.0097(14) 0.0015(13) C33A 0.038(2) 0.0218(19) 0.0212(19) -0.0003(14) 0.0125(18) 0.0046(16) C34 0.037(2) 0.028(2) 0.026(2) 0.0024(15) 0.0110(18) 0.0054(17) C35 0.047(3) 0.033(2) 0.023(2) 0.0029(16) 0.0066(19) 0.011(2) C36 0.058(3) 0.030(2) 0.029(2) 0.0066(17) 0.020(2) 0.010(2) C37 0.050(3) 0.027(2) 0.031(2) 0.0041(16) 0.022(2) 0.0057(19) C37A 0.037(2) 0.0247(19) 0.027(2) -0.0015(15) 0.0155(18) 0.0065(17) Cl1 0.0255(5) 0.0303(5) 0.0251(5) -0.0019(3) 0.0090(4) -0.0070(4) Cl2 0.0307(10) 0.0398(13) 0.0343(10) -0.0051(8) 0.0063(7) 0.0005(8) Cl3 0.071(4) 0.098(5) 0.061(4) 0.001(3) 0.039(3) 0.000(3) O3 0.027(4) 0.057(4) 0.025(4) 0.001(3) -0.006(3) 0.007(3) O4 0.0314(17) 0.077(2) 0.0323(17) 0.0025(16) 0.0097(14) -0.0087(16) O5 0.132(6) 0.319(12) 0.108(6) 0.066(7) 0.030(5) 0.093(7) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Ni1 N21 1.855(3) . ? Ni1 C32 1.913(4) . ? Ni1 C12 1.922(4) . ? Ni1 Cl1 2.1355(11) . ? C1 N11 1.469(5) . ? C1 C2 1.515(5) . ? C1 H1A 0.99 . ? C1 H1B 0.99 . ? C2 C3 1.520(5) . ? C2 H2A 0.99 . ? C2 H2B 0.99 . ? C3 C4 1.526(5) . ? C3 H3A 0.99 . ? C3 H3B 0.99 . ? C4 H4A 0.98 . ? C4 H4B 0.98 . ? C4 H4C 0.98 . ? C5 N31 1.466(5) . ? C5 C6 1.517(5) . ? C5 H5A 0.99 . ? C5 H5B 0.99 . ? C6 C7 1.528(6) . ? C6 H6A 0.99 . ? C6 H6B 0.99 . ? C7 C8 1.528(6) . ? C7 H7A 0.99 . ? C7 H7B 0.99 . ? C8 H8A 0.98 . ? C8 H8B 0.98 . ? C8 H8C 0.98 . ? N11 C12 1.332(5) . ? N11 C17A 1.405(5) . ? C12 N13 1.384(5) . ? N13 C13A 1.397(5) . ? N13 C22 1.400(5) . ? C13A C17A 1.393(5) . ? C13A C14 1.394(5) . ? C14 C15 1.391(5) . ? C14 H14 0.95 . ? C15 C16 1.401(6) . ? C15 H15 0.95 . ? C16 C17 1.386(5) . ? C16 H16 0.95 . ? C17 C17A 1.390(5) . ? C17 H17 0.95 . ? N21 C22 1.342(5) . ? N21 C26 1.342(5) . ? C22 C23 1.389(5) . ? C23 C24 1.386(5) . ? C23 H23 0.95 . ? C24 C25 1.391(6) . ? C24 H24 0.95 . ? C25 C26 1.374(6) . ? C25 H25 0.95 . ? C26 N33 1.402(5) . ? N31 C32 1.346(5) . ? N31 C37A 1.396(5) . ? C32 N33 1.394(5) . ? N33 C33A 1.406(5) . ? C33A C34 1.379(6) . ? C33A C37A 1.394(6) . ? C34 C35 1.395(6) . ? C34 H34 0.95 . ? C35 C36 1.394(7) . ? C35 H35 0.95 . ? C36 C37 1.393(6) . ? C36 H36 0.95 . ? C37 C37A 1.394(6) . ? C37 H37 0.95 . ? 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 N21 Ni1 C32 81.74(15) . . ? N21 Ni1 C12 81.83(14) . . ? C32 Ni1 C12 163.43(16) . . ? N21 Ni1 Cl1 173.13(10) . . ? C32 Ni1 Cl1 98.60(12) . . ? C12 Ni1 Cl1 97.98(11) . . ? N11 C1 C2 113.5(3) . . ? N11 C1 H1A 108.9 . . ? C2 C1 H1A 108.9 . . ? N11 C1 H1B 108.9 . . ? C2 C1 H1B 108.9 . . ? H1A C1 H1B 107.7 . . ? C1 C2 C3 111.4(3) . . ? C1 C2 H2A 109.3 . . ? C3 C2 H2A 109.3 . . ? C1 C2 H2B 109.3 . . ? C3 C2 H2B 109.3 . . ? H2A C2 H2B 108 . . ? C2 C3 C4 112.3(3) . . ? C2 C3 H3A 109.2 . . ? C4 C3 H3A 109.2 . . ? C2 C3 H3B 109.2 . . ? C4 C3 H3B 109.2 . . ? H3A C3 H3B 107.9 . . ? C3 C4 H4A 109.5 . . ? C3 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? C3 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? N31 C5 C6 111.6(3) . . ? N31 C5 H5A 109.3 . . ? C6 C5 H5A 109.3 . . ? N31 C5 H5B 109.3 . . ? C6 C5 H5B 109.3 . . ? H5A C5 H5B 108 . . ? C5 C6 C7 111.0(3) . . ? C5 C6 H6A 109.4 . . ? C7 C6 H6A 109.4 . . ? C5 C6 H6B 109.4 . . ? C7 C6 H6B 109.4 . . ? H6A C6 H6B 108 . . ? C6 C7 C8 112.1(4) . . ? C6 C7 H7A 109.2 . . ? C8 C7 H7A 109.2 . . ? C6 C7 H7B 109.2 . . ? C8 C7 H7B 109.2 . . ? H7A C7 H7B 107.9 . . ? C7 C8 H8A 109.5 . . ? C7 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C7 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C12 N11 C17A 110.7(3) . . ? C12 N11 C1 126.4(3) . . ? C17A N11 C1 122.8(3) . . ? N11 C12 N13 106.0(3) . . ? N11 C12 Ni1 142.2(3) . . ? N13 C12 Ni1 111.8(3) . . ? C12 N13 C13A 111.1(3) . . ? C12 N13 C22 116.3(3) . . ? C13A N13 C22 132.3(3) . . ? C17A C13A C14 121.5(3) . . ? C17A C13A N13 104.8(3) . . ? C14 C13A N13 133.7(3) . . ? C15 C14 C13A 116.6(3) . . ? C15 C14 H14 121.7 . . ? C13A C14 H14 121.7 . . ? C14 C15 C16 121.8(3) . . ? C14 C15 H15 119.1 . . ? C16 C15 H15 119.1 . . ? C17 C16 C15 121.4(3) . . ? C17 C16 H16 119.3 . . ? C15 C16 H16 119.3 . . ? C16 C17 C17A 116.8(3) . . ? C16 C17 H17 121.6 . . ? C17A C17 H17 121.6 . . ? C17 C17A C13A 122.0(3) . . ? C17 C17A N11 130.6(3) . . ? C13A C17A N11 107.4(3) . . ? C22 N21 C26 120.1(3) . . ? C22 N21 Ni1 119.6(3) . . ? C26 N21 Ni1 120.2(3) . . ? N21 C22 C23 121.7(3) . . ? N21 C22 N13 110.0(3) . . ? C23 C22 N13 128.3(3) . . ? C24 C23 C22 117.0(4) . . ? C24 C23 H23 121.5 . . ? C22 C23 H23 121.5 . . ? C23 C24 C25 121.9(4) . . ? C23 C24 H24 119 . . ? C25 C24 H24 119 . . ? C26 C25 C24 116.9(4) . . ? C26 C25 H25 121.6 . . ? C24 C25 H25 121.6 . . ? N21 C26 C25 122.4(4) . . ? N21 C26 N33 109.7(3) . . ? C25 C26 N33 127.9(3) . . ? C32 N31 C37A 111.3(3) . . ? C32 N31 C5 125.6(3) . . ? C37A N31 C5 123.0(3) . . ? N31 C32 N33 104.9(3) . . ? N31 C32 Ni1 142.8(3) . . ? N33 C32 Ni1 112.3(2) . . ? C32 N33 C26 116.0(3) . . ? C32 N33 C33A 111.5(3) . . ? C26 N33 C33A 132.5(3) . . ? C34 C33A C37A 122.4(4) . . ? C34 C33A N33 133.2(4) . . ? C37A C33A N33 104.4(3) . . ? C33A C34 C35 116.0(4) . . ? C33A C34 H34 122 . . ? C35 C34 H34 122 . . ? C36 C35 C34 122.0(4) . . ? C36 C35 H35 119 . . ? C34 C35 H35 119 . . ? C37 C36 C35 121.8(4) . . ? C37 C36 H36 119.1 . . ? C35 C36 H36 119.1 . . ? C36 C37 C37A 116.0(4) . . ? C36 C37 H37 122 . . ? C37A C37 H37 122 . . ? C37 C37A C33A 121.8(4) . . ? C37 C37A N31 130.3(4) . . ? C33A C37A N31 107.9(3) . . ? #===END # Attachment '4953_web_deposit_cif_file_3_BrianSkelton_1302069886.cif' data_dbb100 _database_code_depnum_ccdc_archive 'CCDC 820595' #TrackingRef '4953_web_deposit_cif_file_3_BrianSkelton_1302069886.cif' _audit_creation_date 2009-10-12T14:25:44-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_sum 'C27 H29 Cl2 N5 Ni' _chemical_formula_moiety 'C27 H29 Cl2 N5 Ni' _chemical_formula_weight 553.16 #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 1 21/n 1' _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 13.7294(17) _cell_length_b 8.6736(6) _cell_length_c 20.423(3) _cell_angle_alpha 90 _cell_angle_beta 92.463(10) _cell_angle_gamma 90 _cell_volume 2429.8(5) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 4899 _cell_measurement_theta_min 3.2223 _cell_measurement_theta_max 67.0655 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description needle _exptl_crystal_colour dark_green _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.04 _exptl_crystal_density_diffrn 1.512 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1152 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 3.383 _exptl_absorpt_correction_type analytical _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.48 (release 15-09-2009 CrysAlis171 .NET) (compiled Sep 15 2009,11:49:04) Analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by R.C. Clark & J.S. (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897) ; _exptl_absorpt_correction_T_min 0.665 _exptl_absorpt_correction_T_max 0.861 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_monochromator graphite _diffrn_detector_area_resol_mean 10.4738 _diffrn_orient_matrix_ub_11 -0.0783226941 _diffrn_orient_matrix_ub_12 0.0006978023 _diffrn_orient_matrix_ub_13 -0.0565625361 _diffrn_orient_matrix_ub_21 0.0806728261 _diffrn_orient_matrix_ub_22 0.0057644509 _diffrn_orient_matrix_ub_23 -0.0500452128 _diffrn_orient_matrix_ub_31 0.0022130692 _diffrn_orient_matrix_ub_32 -0.1775966496 _diffrn_orient_matrix_ub_33 -0.0018959415 _diffrn_measurement_device_type 'Oxford Diffraction Gemini, Ruby' _diffrn_measurement_method '\w scans' _diffrn_reflns_av_R_equivalents 0.0740 _diffrn_reflns_av_unetI/netI 0.0557 _diffrn_reflns_number 25729 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 3.8 _diffrn_reflns_theta_max 67.29 _diffrn_reflns_theta_full 67.29 _diffrn_measured_fraction_theta_full 0.987 _diffrn_measured_fraction_theta_max 0.987 _reflns_number_total 4314 _reflns_number_gt 3240 _reflns_threshold_expression I>2\s(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET) (compiled May 6 2009,17:20:42) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET) (compiled May 6 2009,17:20:42) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET) (compiled May 6 2009,17:20:42) ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'OrtepII (Johnson, C. K. (1976)' _computing_publication_material 'WinGX Farrugia, L. J. (1999)' #----------------------------------------------------------------------------# # STRUCTURE SOLUTION #----------------------------------------------------------------------------# _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2\s(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0802P)^2^+22.5951P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_number_reflns 4314 _refine_ls_number_parameters 318 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0944 _refine_ls_R_factor_gt 0.0729 _refine_ls_wR_factor_ref 0.2185 _refine_ls_wR_factor_gt 0.2065 _refine_ls_goodness_of_fit_ref 1.08 _refine_ls_restrained_S_all 1.08 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0 _refine_diff_density_max 1.579 _refine_diff_density_min -0.526 _refine_diff_density_rms 0.139 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ni Ni -3.0029 0.5091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Ni1 Ni 0.50208(8) 0.21459(12) 0.37078(5) 0.0197(3) Uani 1 1 d . . . Cl1 Cl 0.59540(12) 0.40545(18) 0.31276(8) 0.0253(4) Uani 1 1 d . . . Cl2 Cl 0.42451(11) 0.08063(18) 0.28790(7) 0.0236(4) Uani 1 1 d . . . N11 N 0.3266(4) 0.4299(6) 0.3573(3) 0.0215(12) Uani 1 1 d . . . C1 C 0.3125(5) 0.4377(8) 0.2865(3) 0.0240(14) Uani 1 1 d . . . H1A H 0.2422 0.428 0.2745 0.029 Uiso 1 1 calc R . . H1B H 0.3468 0.3502 0.2665 0.029 Uiso 1 1 calc R . . C2 C 0.3513(5) 0.5910(8) 0.2587(3) 0.0254(15) Uani 1 1 d . . . H2A H 0.3111 0.6779 0.2736 0.03 Uiso 1 1 calc R . . H2B H 0.4193 0.6079 0.2753 0.03 Uiso 1 1 calc R . . C3 C 0.3477(5) 0.5858(9) 0.1836(4) 0.0293(16) Uani 1 1 d . . . H3A H 0.2864 0.5354 0.1678 0.035 Uiso 1 1 calc R . . H3B H 0.3476 0.6924 0.1663 0.035 Uiso 1 1 calc R . . C4 C 0.4339(6) 0.4985(9) 0.1577(3) 0.0316(16) Uani 1 1 d . . . H4A H 0.4947 0.5442 0.1754 0.047 Uiso 1 1 calc R . . H4B H 0.432 0.5047 0.1097 0.047 Uiso 1 1 calc R . . H4C H 0.4306 0.3902 0.1712 0.047 Uiso 1 1 calc R . . C12 C 0.3978(5) 0.3502(7) 0.3885(3) 0.0211(13) Uani 1 1 d . . . N13 N 0.3907(4) 0.3820(6) 0.4551(3) 0.0196(11) Uani 1 1 d . . . C13A C 0.3150(5) 0.4863(7) 0.4642(3) 0.0205(13) Uani 1 1 d . . . C14 C 0.2787(5) 0.5587(8) 0.5196(3) 0.0225(14) Uani 1 1 d . . . H14 H 0.3055 0.5388 0.5624 0.027 Uiso 1 1 calc R . . C15 C 0.2025(5) 0.6598(8) 0.5089(3) 0.0236(14) Uani 1 1 d . . . H15 H 0.1771 0.7123 0.5453 0.028 Uiso 1 1 calc R . . C16 C 0.1609(5) 0.6881(8) 0.4459(3) 0.0237(14) Uani 1 1 d . . . H16 H 0.1082 0.7587 0.4409 0.028 Uiso 1 1 calc R . . C17 C 0.1950(5) 0.6151(8) 0.3908(3) 0.0248(14) Uani 1 1 d . . . H17 H 0.1663 0.6321 0.3482 0.03 Uiso 1 1 calc R . . C17A C 0.2732(5) 0.5163(7) 0.4015(3) 0.0213(13) Uani 1 1 d . . . N21 N 0.5166(4) 0.2203(6) 0.4623(3) 0.0194(11) Uani 1 1 d . . . C22 C 0.4565(5) 0.3079(7) 0.4974(3) 0.0197(13) Uani 1 1 d . . . C23 C 0.4632(5) 0.3122(7) 0.5655(3) 0.0207(13) Uani 1 1 d . . . H23 H 0.4217 0.376 0.5897 0.025 Uiso 1 1 calc R . . C24 C 0.5337(5) 0.2184(8) 0.5966(3) 0.0228(14) Uani 1 1 d . . . H24 H 0.5394 0.2168 0.6431 0.027 Uiso 1 1 calc R . . C25 C 0.5960(5) 0.1269(7) 0.5608(3) 0.0221(14) Uani 1 1 d . . . H25 H 0.6441 0.0633 0.5819 0.027 Uiso 1 1 calc R . . C26 C 0.5845(5) 0.1333(7) 0.4938(3) 0.0200(13) Uani 1 1 d . . . N31 N 0.6742(4) 0.0017(6) 0.3473(3) 0.0200(11) Uani 1 1 d . . . C5 C 0.6715(5) -0.0067(8) 0.2753(3) 0.0237(14) Uani 1 1 d . . . H5A H 0.7377 0.012 0.2596 0.028 Uiso 1 1 calc R . . H5B H 0.6278 0.0748 0.2569 0.028 Uiso 1 1 calc R . . C6 C 0.6354(5) -0.1636(8) 0.2513(3) 0.0263(15) Uani 1 1 d . . . H6A H 0.5701 -0.1834 0.2682 0.032 Uiso 1 1 calc R . . H6B H 0.6802 -0.2446 0.2688 0.032 Uiso 1 1 calc R . . C7 C 0.6295(5) -0.1726(9) 0.1760(3) 0.0281(15) Uani 1 1 d . . . H7A H 0.6892 -0.1264 0.1587 0.034 Uiso 1 1 calc R . . H7B H 0.6273 -0.2822 0.1625 0.034 Uiso 1 1 calc R . . C8 C 0.5407(6) -0.0898(9) 0.1460(4) 0.0341(17) Uani 1 1 d . . . H8A H 0.4813 -0.1379 0.1615 0.051 Uiso 1 1 calc R . . H8B H 0.5411 -0.0971 0.0982 0.051 Uiso 1 1 calc R . . H8C H 0.5425 0.0188 0.1592 0.051 Uiso 1 1 calc R . . C32 C 0.6099(5) 0.0789(7) 0.3820(3) 0.0204(13) Uani 1 1 d . . . N33 N 0.6382(4) 0.0527(6) 0.4477(3) 0.0193(11) Uani 1 1 d . . . C33A C 0.7204(5) -0.0412(7) 0.4526(3) 0.0213(13) Uani 1 1 d . . . C34 C 0.7761(5) -0.1018(8) 0.5054(3) 0.0252(14) Uani 1 1 d . . . H34 H 0.7609 -0.0804 0.5494 0.03 Uiso 1 1 calc R . . C35 C 0.8541(5) -0.1939(9) 0.4910(4) 0.0309(16) Uani 1 1 d . . . H35 H 0.8928 -0.2387 0.5257 0.037 Uiso 1 1 calc R . . C36 C 0.8771(5) -0.2226(8) 0.4260(4) 0.0306(16) Uani 1 1 d . . . H36 H 0.932 -0.2854 0.4179 0.037 Uiso 1 1 calc R . . C37 C 0.8235(5) -0.1635(8) 0.3733(4) 0.0286(16) Uani 1 1 d . . . H37 H 0.8406 -0.1818 0.3294 0.034 Uiso 1 1 calc R . . C37A C 0.7423(5) -0.0747(7) 0.3882(3) 0.0197(13) 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 0.0241(6) 0.0180(6) 0.0171(6) -0.0005(4) 0.0010(4) 0.0035(5) Cl1 0.0287(8) 0.0224(8) 0.0252(8) 0.0029(6) 0.0053(6) -0.0004(6) Cl2 0.0268(8) 0.0212(8) 0.0225(8) -0.0039(6) -0.0026(6) 0.0015(6) N11 0.026(3) 0.018(3) 0.019(3) 0.000(2) -0.001(2) 0.004(2) C1 0.025(3) 0.023(4) 0.024(3) -0.006(3) 0.000(3) -0.003(3) C2 0.033(4) 0.014(3) 0.028(4) 0.004(3) 0.001(3) 0.005(3) C3 0.026(4) 0.028(4) 0.034(4) 0.000(3) 0.001(3) 0.002(3) C4 0.043(4) 0.032(4) 0.020(4) -0.002(3) 0.002(3) -0.001(3) C12 0.029(3) 0.015(3) 0.019(3) -0.001(2) -0.004(3) 0.001(3) N13 0.022(3) 0.019(3) 0.018(3) 0.002(2) -0.001(2) -0.001(2) C13A 0.024(3) 0.015(3) 0.022(3) 0.001(2) 0.000(3) -0.002(3) C14 0.022(3) 0.026(4) 0.019(3) 0.002(3) 0.005(3) -0.003(3) C15 0.030(4) 0.019(3) 0.023(3) -0.001(3) 0.009(3) -0.002(3) C16 0.017(3) 0.024(3) 0.030(4) 0.000(3) 0.001(3) 0.004(3) C17 0.026(3) 0.023(3) 0.025(3) 0.001(3) -0.002(3) 0.003(3) C17A 0.022(3) 0.018(3) 0.024(3) 0.002(3) 0.003(3) 0.002(3) N21 0.024(3) 0.012(2) 0.022(3) 0.002(2) 0.000(2) -0.003(2) C22 0.022(3) 0.013(3) 0.024(3) -0.001(2) 0.005(3) 0.000(3) C23 0.023(3) 0.018(3) 0.022(3) 0.000(3) 0.000(3) -0.001(3) C24 0.028(3) 0.020(3) 0.021(3) 0.001(3) 0.001(3) -0.006(3) C25 0.024(3) 0.021(3) 0.021(3) 0.001(3) -0.003(3) 0.001(3) C26 0.020(3) 0.018(3) 0.022(3) -0.002(3) 0.001(2) 0.000(3) N31 0.018(3) 0.018(3) 0.024(3) -0.001(2) 0.002(2) 0.001(2) C5 0.025(3) 0.025(4) 0.022(3) 0.001(3) 0.003(3) 0.005(3) C6 0.030(4) 0.023(4) 0.027(4) -0.002(3) 0.003(3) -0.001(3) C7 0.026(4) 0.034(4) 0.024(4) -0.004(3) 0.004(3) 0.000(3) C8 0.040(4) 0.034(4) 0.029(4) -0.002(3) 0.001(3) -0.003(3) C32 0.025(3) 0.013(3) 0.022(3) 0.000(2) 0.000(3) -0.001(3) N33 0.022(3) 0.019(3) 0.018(3) 0.000(2) 0.002(2) -0.002(2) C33A 0.019(3) 0.018(3) 0.026(3) 0.001(3) -0.002(3) 0.000(3) C34 0.026(3) 0.022(3) 0.027(4) 0.002(3) -0.004(3) 0.004(3) C35 0.028(4) 0.032(4) 0.032(4) 0.001(3) -0.005(3) 0.003(3) C36 0.026(4) 0.023(4) 0.042(4) -0.004(3) -0.002(3) 0.006(3) C37 0.029(4) 0.027(4) 0.031(4) -0.005(3) 0.008(3) 0.002(3) C37A 0.019(3) 0.013(3) 0.027(3) -0.001(2) 0.003(3) 0.000(2) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Ni1 N21 1.871(5) . ? Ni1 C32 1.897(6) . ? Ni1 C12 1.900(7) . ? Ni1 Cl2 2.2791(18) . ? Ni1 Cl1 2.4324(19) . ? N11 C12 1.336(8) . ? N11 C17A 1.403(8) . ? N11 C1 1.452(8) . ? C1 C2 1.549(9) . ? C1 H1A 0.99 . ? C1 H1B 0.99 . ? C2 C3 1.532(10) . ? C2 H2A 0.99 . ? C2 H2B 0.99 . ? C3 C4 1.519(10) . ? C3 H3A 0.99 . ? C3 H3B 0.99 . ? C4 H4A 0.98 . ? C4 H4B 0.98 . ? C4 H4C 0.98 . ? C12 N13 1.394(8) . ? N13 C22 1.383(8) . ? N13 C13A 1.397(8) . ? C13A C14 1.403(9) . ? C13A C17A 1.405(9) . ? C14 C15 1.376(10) . ? C14 H14 0.95 . ? C15 C16 1.406(9) . ? C15 H15 0.95 . ? C16 C17 1.391(10) . ? C16 H16 0.95 . ? C17 C17A 1.384(9) . ? C17 H17 0.95 . ? N21 C26 1.343(8) . ? N21 C22 1.350(8) . ? C22 C23 1.389(9) . ? C23 C24 1.396(9) . ? C23 H23 0.95 . ? C24 C25 1.395(9) . ? C24 H24 0.95 . ? C25 C26 1.373(9) . ? C25 H25 0.95 . ? C26 N33 1.406(8) . ? N31 C32 1.336(8) . ? N31 C37A 1.395(8) . ? N31 C5 1.471(8) . ? C5 C6 1.522(9) . ? C5 H5A 0.99 . ? C5 H5B 0.99 . ? C6 C7 1.539(9) . ? C6 H6A 0.99 . ? C6 H6B 0.99 . ? C7 C8 1.521(10) . ? C7 H7A 0.99 . ? C7 H7B 0.99 . ? C8 H8A 0.98 . ? C8 H8B 0.98 . ? C8 H8C 0.98 . ? C32 N33 1.399(8) . ? N33 C33A 1.392(8) . ? C33A C37A 1.393(9) . ? C33A C34 1.398(9) . ? C34 C35 1.378(10) . ? C34 H34 0.95 . ? C35 C36 1.400(11) . ? C35 H35 0.95 . ? C36 C37 1.377(10) . ? C36 H36 0.95 . ? C37 C37A 1.399(9) . ? C37 H37 0.95 . ? 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 N21 Ni1 C32 81.2(3) . . ? N21 Ni1 C12 80.9(3) . . ? C32 Ni1 C12 162.0(3) . . ? N21 Ni1 Cl2 141.38(17) . . ? C32 Ni1 Cl2 96.4(2) . . ? C12 Ni1 Cl2 97.2(2) . . ? N21 Ni1 Cl1 115.64(17) . . ? C32 Ni1 Cl1 93.3(2) . . ? C12 Ni1 Cl1 95.1(2) . . ? Cl2 Ni1 Cl1 102.96(7) . . ? C12 N11 C17A 111.2(5) . . ? C12 N11 C1 124.2(6) . . ? C17A N11 C1 124.3(5) . . ? N11 C1 C2 111.8(5) . . ? N11 C1 H1A 109.2 . . ? C2 C1 H1A 109.2 . . ? N11 C1 H1B 109.2 . . ? C2 C1 H1B 109.2 . . ? H1A C1 H1B 107.9 . . ? C3 C2 C1 110.2(6) . . ? C3 C2 H2A 109.6 . . ? C1 C2 H2A 109.6 . . ? C3 C2 H2B 109.6 . . ? C1 C2 H2B 109.6 . . ? H2A C2 H2B 108.1 . . ? C4 C3 C2 111.8(6) . . ? C4 C3 H3A 109.3 . . ? C2 C3 H3A 109.3 . . ? C4 C3 H3B 109.3 . . ? C2 C3 H3B 109.3 . . ? H3A C3 H3B 107.9 . . ? C3 C4 H4A 109.5 . . ? C3 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? C3 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? N11 C12 N13 106.4(5) . . ? N11 C12 Ni1 140.5(5) . . ? N13 C12 Ni1 113.2(4) . . ? C22 N13 C12 116.5(5) . . ? C22 N13 C13A 133.4(5) . . ? C12 N13 C13A 110.0(5) . . ? N13 C13A C14 133.6(6) . . ? N13 C13A C17A 105.9(5) . . ? C14 C13A C17A 120.4(6) . . ? C15 C14 C13A 116.8(6) . . ? C15 C14 H14 121.6 . . ? C13A C14 H14 121.6 . . ? C14 C15 C16 122.2(6) . . ? C14 C15 H15 118.9 . . ? C16 C15 H15 118.9 . . ? C17 C16 C15 121.6(6) . . ? C17 C16 H16 119.2 . . ? C15 C16 H16 119.2 . . ? C17A C17 C16 116.1(6) . . ? C17A C17 H17 122 . . ? C16 C17 H17 122 . . ? C17 C17A N11 130.7(6) . . ? C17 C17A C13A 122.8(6) . . ? N11 C17A C13A 106.4(5) . . ? C26 N21 C22 119.3(6) . . ? C26 N21 Ni1 120.4(4) . . ? C22 N21 Ni1 120.3(4) . . ? N21 C22 N13 109.1(5) . . ? N21 C22 C23 122.1(6) . . ? N13 C22 C23 128.8(6) . . ? C22 C23 C24 117.0(6) . . ? C22 C23 H23 121.5 . . ? C24 C23 H23 121.5 . . ? C25 C24 C23 121.5(6) . . ? C25 C24 H24 119.3 . . ? C23 C24 H24 119.3 . . ? C26 C25 C24 116.9(6) . . ? C26 C25 H25 121.6 . . ? C24 C25 H25 121.6 . . ? N21 C26 C25 123.3(6) . . ? N21 C26 N33 109.4(5) . . ? C25 C26 N33 127.4(6) . . ? C32 N31 C37A 111.2(5) . . ? C32 N31 C5 124.5(5) . . ? C37A N31 C5 124.2(5) . . ? N31 C5 C6 111.1(5) . . ? N31 C5 H5A 109.4 . . ? C6 C5 H5A 109.4 . . ? N31 C5 H5B 109.4 . . ? C6 C5 H5B 109.4 . . ? H5A C5 H5B 108 . . ? C5 C6 C7 111.7(6) . . ? C5 C6 H6A 109.3 . . ? C7 C6 H6A 109.3 . . ? C5 C6 H6B 109.3 . . ? C7 C6 H6B 109.3 . . ? H6A C6 H6B 107.9 . . ? C8 C7 C6 112.7(6) . . ? C8 C7 H7A 109.1 . . ? C6 C7 H7A 109.1 . . ? C8 C7 H7B 109.1 . . ? C6 C7 H7B 109.1 . . ? H7A C7 H7B 107.8 . . ? C7 C8 H8A 109.5 . . ? C7 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C7 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? N31 C32 N33 105.3(5) . . ? N31 C32 Ni1 141.0(5) . . ? N33 C32 Ni1 113.6(4) . . ? C33A N33 C32 110.8(5) . . ? C33A N33 C26 133.6(5) . . ? C32 N33 C26 115.4(5) . . ? N33 C33A C37A 105.2(5) . . ? N33 C33A C34 133.7(6) . . ? C37A C33A C34 121.1(6) . . ? C35 C34 C33A 117.3(7) . . ? C35 C34 H34 121.4 . . ? C33A C34 H34 121.4 . . ? C34 C35 C36 121.0(7) . . ? C34 C35 H35 119.5 . . ? C36 C35 H35 119.5 . . ? C37 C36 C35 122.7(7) . . ? C37 C36 H36 118.6 . . ? C35 C36 H36 118.6 . . ? C36 C37 C37A 116.0(7) . . ? C36 C37 H37 122 . . ? C37A C37 H37 122 . . ? C33A C37A N31 107.4(5) . . ? C33A C37A C37 121.8(6) . . ? N31 C37A C37 130.7(6) . . ? #===END