data_global _journal_name_full 'Dalton Trans.' _journal_coden_cambridge 0222 #============================================================================== # 1. SUBMISSION DETAILS #============================================================================== _publ_contact_author_name 'Prof. Garry Hanan' _publ_contact_author_address ; D\'epartement de Chimie Universit\'e de Montr\'eal C.P. 6128, Succ. Centre-ville Montr\'eal, Qu\'ebec Canada H3C 3J7 ; _publ_contact_author_phone '+1 514 343 7056' _publ_contact_author_fax '+1 514 343 7586' _publ_contact_author_email garry.hanan@umontreal.ca _publ_requested_category FO #============================================================================== # 3. TITLE AND AUTHOR LIST #============================================================================== _publ_section_title ; Non-covalent polymerisation in the solid-state: halogen-halogen vs methyl-methyl interactions in the complexes of 2,4-di(2-pyridyl)-1,3,5-triazine ligands ; # The loop structure below should contain the names and addresses of all # authors, in the required order of publication. Repeat as necessary. loop_ _publ_author_name _publ_author_address G.S.Hanan ; D\'epartement de Chimie Universit\'e de Montr\'eal C.P. 6128, Succ. Centre-ville, Montr\'eal, Qu\'ebec Canada H3C 3J7 ; E.A.Medlycott ; D\'epartement de Chimie Universit\'e de Montr\'eal C.P. 6128, Succ. Centre-ville, Montr\'eal, Qu\'ebec Canada H3C 3J7 ; K.A.Udachin ; Steacie Institute for Molecular Sciences, NRC, Ottawa, Ontario, Canada. ; #============================================================================== # 4. TEXT #============================================================================== _publ_section_exptl_refinement ; All non-H atoms were refined by full-matrix least-squares with anisotropic displacement parameters. The H atoms were generated geometrically (C-H 0.95 to 0.98, \%A) and were included in the refinement in the riding model approximation; their temperature factors were set to 1.5 times those of the equivalent isotropic temperature factors of the parent site (methyl) and 1.2 times for others. A final verification of possible voids was performed using the VOID routine of the PLATON program (Spek, 2000). ; _publ_section_references ; Bruker (1997). SHELXTL (1997). Release 5.10; The Complete Software Package for Single Crystal Structure Determination. Bruker AXS Inc., Madison, USA. Bruker (1999a). SAINT Release 6.06. Integration Software for Single Crystal Data. Bruker AXS Inc., Madison, USA. Bruker (1999b). SMART Release 5.059; Bruker Molecular Analysis Research Tool, Bruker AXS Inc., Madison, USA. Sheldrick, G. M. (1986). SHELXS86. Program for Crystal Structure solution. University of G\"ottingen, Germany. Sheldrick, G. M. (1996). SADABS, Bruker Area Detector Absorption Corrections. Bruker AXS Inc., Madison, USA. Sheldrick, G. M. (1997a). SHELXS97. Program for Crystal Structure solution. University of G\"ottingen, Germany. Sheldrick, G. M. (1997b). SHELXL97. Program for crystal structure refinement. University of G\"ottingen, Germany. Spek, A. L. (2000). PLATON, 2000 version; Molecular Geometry Program, University of Utrecht, Utrecht, Holland. ; _publ_section_figure_captions ; Fig 1 Ortep view of the title compound. Thermal ellipsoids are shown at 30% probability levels. ; _publ_section_table_legends ; Table 1. Selected geometric parameters (\%A, \%) for the title compound. ; _publ_section_acknowledgements ; We are grateful to the Natural Sciences and Engineering Research Council of Canada and the Minist\`ere de l'Education du Qu\'ebec for financial support. ; # ======================================================== # STRUCTURAL DATA # ======================================================== data_gary62 _database_code_depnum_ccdc_archive 'CCDC 611625' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C38 H24 Br2 Fe N10 ,2(PF6)' _chemical_formula_sum 'C38 H24 Br2 F12 Fe N10 P2' _chemical_formula_weight 1126.28 _chemical_compound_source 'Synthesized by the authors. See text' 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 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Fe Fe -1.1336 3.1974 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M C2/c _symmetry_space_group_name_hall '-C 2yc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 14.4472(6) _cell_length_b 21.0450(12) _cell_length_c 16.4940(9) _cell_angle_alpha 90.00 _cell_angle_beta 99.350(4) _cell_angle_gamma 90.00 _cell_volume 4948.2(4) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 4281 _cell_measurement_theta_min 2.72 _cell_measurement_theta_max 72.72 _exptl_crystal_description block _exptl_crystal_colour purple _exptl_crystal_size_max 0.36 _exptl_crystal_size_mid 0.19 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.512 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2224 _exptl_absorpt_coefficient_mu 5.699 _exptl_absorpt_correction_Type multi-scan _exptl_absorpt_correction_T_min 0.2000 _exptl_absorpt_correction_T_max 0.67 _exptl_absorpt_process_details 'Sadabs (Sheldrick,1996)' _exptl_special_details ; X-ray crystallographic data for I were collected from a single crystal sample, which was mounted on a loop fiber. Data were collected using a Bruker Platform diffractometer, equipped with a Bruker SMART 2K Charged-Coupled Device (CCD) Area Detector using the program SMART and normal focus sealed tube source graphite monochromated Cu-K\a radiation. The crystal-to-detector distance was 4.908 cm, and the data collection was carried out in 512 x 512 pixel mode, utilizing 4 x 4 pixel binning. The initial unit cell parameters were determined by a least-squares fit of the angular setting of strong reflections, collected by a 9.0 degree scan in 30 frames over four different parts of the reciprocal space (120 frames total). One complete sphere of data was collected, to better than 0.8\%A resolution. Upon completion of the data collection, the first 101 frames were recollected in order to improve the decay correction analysis. ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'Sealed Tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker AXS Smart 2K/Platform' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 5.5 _diffrn_standards_number 5 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0.00 _diffrn_reflns_number 40326 _diffrn_reflns_av_R_equivalents 0.065 _diffrn_reflns_av_sigmaI/netI 0.0837 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -25 _diffrn_reflns_limit_k_max 25 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 3.74 _diffrn_reflns_theta_max 73.02 _reflns_number_total 4826 _reflns_number_gt 3105 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'SMART (Bruker, 1999)' _computing_cell_refinement 'SMART (Bruker, 1999)' _computing_data_reduction 'SAINT (Bruker, 1999)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL (Bruker, 1997)' _computing_publication_material 'UdMX (local program)' _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^)+(0.1800P)^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_extinction_coef ? _refine_ls_number_reflns 4826 _refine_ls_number_parameters 361 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1280 _refine_ls_R_factor_gt 0.0961 _refine_ls_wR_factor_ref 0.2890 _refine_ls_wR_factor_gt 0.2665 _refine_ls_goodness_of_fit_ref 1.089 _refine_ls_restrained_S_all 1.089 _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 Fe Fe 0.5000 0.26153(7) 0.2500 0.0230(4) Uani 1 2 d S . . N1 N 0.4730(4) 0.1947(3) 0.1626(4) 0.0343(15) Uani 1 1 d . . . N2 N 0.6137(4) 0.2605(3) 0.2094(3) 0.0215(11) Uani 1 1 d . . . N3 N 0.5704(4) 0.3290(3) 0.3203(3) 0.0267(13) Uani 1 1 d . . . N4 N 0.7090(4) 0.2159(3) 0.1210(4) 0.0300(13) Uani 1 1 d . . . N5 N 0.7699(4) 0.2961(3) 0.2212(4) 0.0263(13) Uani 1 1 d . . . C1 C 0.3933(6) 0.1614(4) 0.1420(6) 0.051(3) Uani 1 1 d . . . H1 H 0.3421 0.1699 0.1699 0.061 Uiso 1 1 calc R . . C2 C 0.3834(7) 0.1163(6) 0.0830(9) 0.080(4) Uani 1 1 d . . . H2 H 0.3257 0.0940 0.0696 0.096 Uiso 1 1 calc R . . C3 C 0.4595(7) 0.1021(5) 0.0409(6) 0.056(3) Uani 1 1 d . . . H3 H 0.4544 0.0694 0.0007 0.068 Uiso 1 1 calc R . . C4 C 0.5395(6) 0.1366(4) 0.0598(5) 0.044(2) Uani 1 1 d . . . H4 H 0.5905 0.1298 0.0311 0.052 Uiso 1 1 calc R . . C5 C 0.5459(5) 0.1818(4) 0.1214(5) 0.0345(17) Uani 1 1 d . . . C6 C 0.6292(5) 0.2204(3) 0.1501(4) 0.0250(14) Uani 1 1 d . . . C7 C 0.7794(5) 0.2542(3) 0.1596(4) 0.0261(15) Uani 1 1 d . . . C8 C 0.6867(4) 0.2974(3) 0.2434(4) 0.0239(14) Uani 1 1 d . . . C9 C 0.6592(5) 0.3395(4) 0.3064(4) 0.0275(15) Uani 1 1 d . . . C10 C 0.7151(5) 0.3865(4) 0.3446(4) 0.0337(17) Uani 1 1 d . . . H10 H 0.7774 0.3917 0.3342 0.040 Uiso 1 1 calc R . . C11 C 0.6790(6) 0.4275(4) 0.3999(5) 0.0401(19) Uani 1 1 d . . . H11 H 0.7156 0.4614 0.4261 0.048 Uiso 1 1 calc R . . C12 C 0.5901(5) 0.4168(4) 0.4143(4) 0.0340(17) Uani 1 1 d . . . H12 H 0.5645 0.4431 0.4519 0.041 Uiso 1 1 calc R . . C13 C 0.5359(5) 0.3671(3) 0.3738(4) 0.0287(15) Uani 1 1 d . . . H13 H 0.4741 0.3602 0.3845 0.034 Uiso 1 1 calc R . . C14 C 0.8707(5) 0.2494(3) 0.1334(4) 0.0265(15) Uani 1 1 d . . . C15 C 0.9372(5) 0.2969(4) 0.1518(5) 0.0395(19) Uani 1 1 d . . . H15 H 0.9227 0.3344 0.1794 0.047 Uiso 1 1 calc R . . C16 C 1.0254(6) 0.2893(5) 0.1294(6) 0.051(2) Uani 1 1 d . . . H16 H 1.0720 0.3210 0.1435 0.061 Uiso 1 1 calc R . . C17 C 1.0446(5) 0.2383(5) 0.0888(5) 0.051(3) Uani 1 1 d . . . C18 C 0.9789(5) 0.1893(4) 0.0691(5) 0.0388(19) Uani 1 1 d . . . H18 H 0.9948 0.1523 0.0412 0.047 Uiso 1 1 calc R . . C19 C 0.8914(5) 0.1955(5) 0.0906(5) 0.040(2) Uani 1 1 d . . . H19 H 0.8454 0.1634 0.0763 0.048 Uiso 1 1 calc R . . Br1 Br 1.16456(6) 0.22803(8) 0.05655(9) 0.0934(7) Uani 1 1 d . . . P1 P 0.7049(12) 0.5551(7) 0.5809(8) 0.040(3) Uani 0.51(4) 1 d P A -2 F11 F 0.6034(13) 0.5461(9) 0.5197(14) 0.071(6) Uani 0.51(4) 1 d P A -2 F12 F 0.748(2) 0.5643(12) 0.4918(16) 0.109(10) Uani 0.51(4) 1 d P A -2 F13 F 0.6816(10) 0.6312(8) 0.5779(9) 0.039(4) Uani 0.51(4) 1 d P A -2 F14 F 0.6420(14) 0.5553(9) 0.6560(11) 0.046(5) Uani 0.51(4) 1 d P A -2 F15 F 0.7057(17) 0.4790(15) 0.592(2) 0.035(5) Uani 0.51(4) 1 d P A -2 F16 F 0.804(2) 0.5565(13) 0.6518(11) 0.068(6) Uani 0.51(4) 1 d P A -2 P11 P 0.7195(14) 0.5584(6) 0.5808(8) 0.046(4) Uani 0.49(4) 1 d P A -1 F111 F 0.631(2) 0.5581(11) 0.5148(11) 0.076(8) Uani 0.49(4) 1 d P A -1 F112 F 0.7805(17) 0.5417(12) 0.5138(11) 0.077(8) Uani 0.49(4) 1 d P A -1 F113 F 0.733(3) 0.6299(9) 0.5699(12) 0.095(11) Uani 0.49(4) 1 d P A -1 F114 F 0.673(2) 0.5694(13) 0.6558(16) 0.100(10) Uani 0.49(4) 1 d P A -1 F115 F 0.724(2) 0.4860(17) 0.580(2) 0.058(8) Uani 0.49(4) 1 d P A -1 F116 F 0.8094(19) 0.5722(19) 0.625(3) 0.134(15) Uani 0.49(4) 1 d P A -1 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 Fe 0.0178(8) 0.0231(8) 0.0295(9) 0.000 0.0081(6) 0.000 N1 0.028(3) 0.041(4) 0.039(4) -0.013(3) 0.018(3) -0.007(3) N2 0.018(3) 0.027(3) 0.022(3) -0.003(2) 0.010(2) 0.002(2) N3 0.022(3) 0.037(3) 0.022(3) 0.005(2) 0.006(2) 0.006(2) N4 0.026(3) 0.038(4) 0.030(3) 0.002(3) 0.015(2) 0.006(3) N5 0.024(3) 0.027(3) 0.028(3) 0.006(2) 0.004(2) -0.003(2) C1 0.031(4) 0.052(6) 0.077(7) -0.035(5) 0.033(4) -0.025(4) C2 0.042(5) 0.069(7) 0.137(11) -0.055(7) 0.036(6) -0.027(5) C3 0.054(6) 0.048(6) 0.072(7) -0.036(5) 0.026(5) -0.015(4) C4 0.034(4) 0.054(6) 0.045(5) -0.018(4) 0.013(4) -0.005(4) C5 0.033(4) 0.042(5) 0.031(4) -0.005(3) 0.013(3) 0.001(3) C6 0.016(3) 0.027(4) 0.034(4) 0.003(3) 0.008(3) -0.001(3) C7 0.016(3) 0.036(4) 0.027(4) 0.004(3) 0.006(3) 0.003(3) C8 0.016(3) 0.034(4) 0.023(3) 0.003(3) 0.005(2) -0.001(3) C9 0.021(3) 0.040(4) 0.021(3) 0.003(3) 0.002(3) 0.004(3) C10 0.020(3) 0.046(5) 0.034(4) -0.007(3) 0.004(3) 0.003(3) C11 0.043(5) 0.043(5) 0.034(4) -0.015(3) 0.003(3) -0.004(4) C12 0.041(4) 0.041(5) 0.020(4) -0.006(3) 0.005(3) 0.004(3) C13 0.025(4) 0.035(4) 0.026(4) -0.003(3) 0.001(3) 0.007(3) C14 0.024(4) 0.030(4) 0.027(4) 0.008(3) 0.008(3) 0.005(3) C15 0.025(4) 0.043(5) 0.054(5) -0.010(4) 0.018(3) -0.007(3) C16 0.027(4) 0.060(6) 0.068(6) -0.020(5) 0.015(4) -0.010(4) C17 0.005(3) 0.102(8) 0.046(5) -0.030(5) 0.008(3) -0.001(4) C18 0.029(4) 0.063(6) 0.024(4) -0.009(4) 0.006(3) 0.000(4) C19 0.020(4) 0.072(6) 0.030(4) -0.011(4) 0.011(3) 0.000(4) Br1 0.0181(5) 0.1478(14) 0.1209(12) -0.0874(10) 0.0311(5) -0.0196(6) P1 0.031(4) 0.060(7) 0.025(4) -0.027(4) -0.005(2) 0.009(3) F11 0.026(7) 0.052(9) 0.130(15) -0.061(10) -0.009(7) -0.004(6) F12 0.19(2) 0.099(15) 0.054(14) -0.015(10) 0.068(14) 0.011(16) F13 0.039(7) 0.052(7) 0.025(6) -0.008(4) -0.002(5) 0.003(6) F14 0.047(9) 0.048(9) 0.041(7) -0.014(6) -0.003(6) 0.022(7) F15 0.024(6) 0.034(9) 0.049(10) 0.008(6) 0.013(5) 0.011(5) F16 0.070(11) 0.100(13) 0.027(7) 0.004(7) -0.014(6) -0.012(9) P11 0.069(9) 0.031(4) 0.031(5) 0.011(4) -0.013(4) -0.009(4) F111 0.084(16) 0.064(11) 0.057(9) 0.016(8) -0.053(10) 0.000(10) F112 0.102(14) 0.095(15) 0.035(8) -0.008(8) 0.013(8) -0.084(13) F113 0.17(3) 0.057(9) 0.040(9) -0.018(7) -0.030(13) -0.022(15) F114 0.104(18) 0.125(17) 0.081(12) -0.072(12) 0.045(12) -0.047(14) F115 0.09(2) 0.037(10) 0.037(11) -0.006(9) -0.023(12) 0.009(13) F116 0.058(13) 0.14(2) 0.19(3) -0.13(2) -0.042(17) 0.035(15) _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_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag Fe N2 . . 1.872(5) Y Fe N2 . 2_655 1.872(5) Y Fe N3 . . 2.004(6) Y Fe N3 . 2_655 2.004(6) Y Fe N1 . . 2.006(6) Y Fe N1 . 2_655 2.006(6) Y N1 C1 . . 1.344(9) Y N1 C5 . . 1.371(9) Y N2 C6 . . 1.338(9) Y N2 C8 . . 1.356(8) Y N3 C13 . . 1.346(9) Y N3 C9 . . 1.357(8) Y N4 C6 . . 1.323(8) Y N4 C7 . . 1.370(9) Y N5 C8 . . 1.312(8) Y N5 C7 . . 1.370(9) Y C1 C2 . . 1.351(13) Y C1 H1 . . 0.95 ? C2 C3 . . 1.425(13) Y C2 H2 . . 0.95 ? C3 C4 . . 1.358(11) Y C3 H3 . . 0.95 ? C4 C5 . . 1.384(10) Y C4 H4 . . 0.95 ? C5 C6 . . 1.465(10) Y C7 C14 . . 1.455(9) Y C8 C9 . . 1.468(9) Y C9 C10 . . 1.366(10) Y C10 C11 . . 1.415(10) Y C10 H10 . . 0.95 ? C11 C12 . . 1.362(11) Y C11 H11 . . 0.95 ? C12 C13 . . 1.408(10) Y C12 H12 . . 0.95 ? C13 H13 . . 0.95 ? C14 C15 . . 1.386(10) Y C14 C19 . . 1.394(11) Y C15 C16 . . 1.393(10) Y C15 H15 . . 0.95 ? C16 C17 . . 1.318(12) Y C16 H16 . . 0.95 ? C17 C18 . . 1.403(12) Y C17 Br1 . . 1.906(7) Y C18 C19 . . 1.374(10) Y C18 H18 . . 0.95 ? C19 H19 . . 0.95 ? P1 F15 . . 1.61(4) Y P1 F13 . . 1.63(2) Y P1 F11 . . 1.65(2) Y P1 F14 . . 1.65(2) Y P1 F16 . . 1.69(3) Y P1 F12 . . 1.70(3) Y P11 F116 . . 1.41(3) Y P11 F114 . . 1.52(3) Y P11 F115 . . 1.53(4) Y P11 F113 . . 1.53(2) Y P11 F111 . . 1.54(2) Y P11 F112 . . 1.56(3) Y F113 F116 . . 1.78(6) Y loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_2 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag N2 FE N2 . . 2_655 178.6(3) Y N2 FE N3 . . . 79.8(2) Y N2 FE N3 2_655 . . 101.2(2) Y N2 FE N3 . . 2_655 101.2(2) Y N2 FE N3 2_655 . 2_655 79.8(2) Y N3 FE N3 . . 2_655 89.7(3) Y N2 FE N1 . . . 79.3(2) Y N2 FE N1 2_655 . . 99.7(2) Y N3 FE N1 . . . 159.0(2) Y N3 FE N1 2_655 . . 93.4(3) Y N2 FE N1 . . 2_655 99.7(2) Y N2 FE N1 2_655 . 2_655 79.3(2) Y N3 FE N1 . . 2_655 93.4(3) Y N3 FE N1 2_655 . 2_655 159.0(2) Y N1 FE N1 . . 2_655 91.0(4) Y C1 N1 C5 . . . 117.9(6) Y C1 N1 FE . . . 127.3(5) Y C5 N1 FE . . . 114.8(5) Y C6 N2 C8 . . . 116.9(5) Y C6 N2 FE . . . 122.0(5) Y C8 N2 FE . . . 120.9(4) Y C13 N3 C9 . . . 118.4(6) Y C13 N3 FE . . . 126.4(5) Y C9 N3 FE . . . 115.0(5) Y C6 N4 C7 . . . 114.5(6) Y C8 N5 C7 . . . 115.3(6) Y N1 C1 C2 . . . 122.4(7) Y N1 C1 H1 . . . 118.8 ? C2 C1 H1 . . . 118.8 ? C1 C2 C3 . . . 119.9(8) Y C1 C2 H2 . . . 120.1 ? C3 C2 H2 . . . 120.1 ? C4 C3 C2 . . . 118.1(8) Y C4 C3 H3 . . . 120.9 ? C2 C3 H3 . . . 120.9 ? C3 C4 C5 . . . 119.3(7) Y C3 C4 H4 . . . 120.3 ? C5 C4 H4 . . . 120.3 ? N1 C5 C4 . . . 122.3(7) Y N1 C5 C6 . . . 112.8(6) Y C4 C5 C6 . . . 124.9(7) Y N4 C6 N2 . . . 124.7(6) Y N4 C6 C5 . . . 124.2(7) Y N2 C6 C5 . . . 111.1(6) Y N4 C7 N5 . . . 124.5(6) Y N4 C7 C14 . . . 117.5(6) Y N5 C7 C14 . . . 118.0(6) Y N5 C8 N2 . . . 124.0(6) Y N5 C8 C9 . . . 125.1(6) Y N2 C8 C9 . . . 110.9(5) Y N3 C9 C10 . . . 122.9(7) Y N3 C9 C8 . . . 113.2(6) Y C10 C9 C8 . . . 123.8(6) Y C9 C10 C11 . . . 119.1(7) Y C9 C10 H10 . . . 120.4 ? C11 C10 H10 . . . 120.4 ? C12 C11 C10 . . . 117.9(7) Y C12 C11 H11 . . . 121 ? C10 C11 H11 . . . 121 ? C11 C12 C13 . . . 120.5(7) Y C11 C12 H12 . . . 119.8 ? C13 C12 H12 . . . 119.8 ? N3 C13 C12 . . . 121.1(7) Y N3 C13 H13 . . . 119.5 ? C12 C13 H13 . . . 119.5 ? C15 C14 C19 . . . 119.9(7) Y C15 C14 C7 . . . 120.9(7) Y C19 C14 C7 . . . 119.1(7) Y C14 C15 C16 . . . 119.3(8) Y C14 C15 H15 . . . 120.3 ? C16 C15 H15 . . . 120.3 ? C17 C16 C15 . . . 120.4(8) Y C17 C16 H16 . . . 119.8 ? C15 C16 H16 . . . 119.8 ? C16 C17 C18 . . . 121.7(7) Y C16 C17 BR1 . . . 120.7(7) Y C18 C17 BR1 . . . 117.6(6) Y C19 C18 C17 . . . 119.1(8) Y C19 C18 H18 . . . 120.5 ? C17 C18 H18 . . . 120.5 ? C18 C19 C14 . . . 119.4(8) Y C18 C19 H19 . . . 120.3 ? C14 C19 H19 . . . 120.3 ? F15 P1 F13 . . . 166.90(13) Y F15 P1 F11 . . . 86.70(15) Y F13 P1 F11 . . . 86.3(1) Y F15 P1 F14 . . . 85.00(12) Y F13 P1 F14 . . . 83.3(9) Y F11 P1 F14 . . . 85.10(13) Y F15 P1 F16 . . . 87.10(16) Y F13 P1 F16 . . . 98.70(13) Y F11 P1 F16 . . . 172.10(15) Y F14 P1 F16 . . . 89.30(12) Y F15 P1 F12 . . . 102.30(14) Y F13 P1 F12 . . . 88.00(13) Y F11 P1 F12 . . . 84.10(13) Y F14 P1 F12 . . . 166.60(17) Y F16 P1 F12 . . . 102.10(15) Y F116 P11 F114 . . . 92.60(19) Y F116 P11 F115 . . . 100(2) Y F114 P11 F115 . . . 100.50(19) Y F116 P11 F113 . . . 74(3) Y F114 P11 F113 . . . 91.80(16) Y F115 P11 F113 . . . 167(3) Y F116 P11 F111 . . . 162(3) Y F114 P11 F111 . . . 98.70(18) Y F115 P11 F111 . . . 91.50(17) Y F113 P11 F111 . . . 91.80(12) Y F116 P11 F112 . . . 80.20(19) Y F114 P11 F112 . . . 170.60(18) Y F115 P11 F112 . . . 74.90(19) Y F113 P11 F112 . . . 92.20(13) Y F111 P11 F112 . . . 89.80(13) Y P11 F113 F116 . . . 49.70(14) Y P11 F116 F113 . . . 56(2) Y loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion _geom_torsion_publ_flag N2 FE N1 C1 . . . . 179.9(8) N N2 FE N1 C1 2_655 . . . 0.8(8) N N3 FE N1 C1 . . . . -177.5(8) N N3 FE N1 C1 2_655 . . . -79.4(8) N N1 FE N1 C1 2_655 . . . 80.1(8) N N2 FE N1 C5 . . . . 1.2(6) N N2 FE N1 C5 2_655 . . . -177.8(6) N N3 FE N1 C5 . . . . 3.80(11) N N3 FE N1 C5 2_655 . . . 101.9(6) N N1 FE N1 C5 2_655 . . . -98.5(6) N N3 FE N2 C6 . . . . 178.9(6) N N3 FE N2 C6 2_655 . . . -93.4(6) N N1 FE N2 C6 . . . . -2.0(5) N N1 FE N2 C6 2_655 . . . 87.2(6) N N3 FE N2 C8 . . . . 3.7(5) N N3 FE N2 C8 2_655 . . . 91.4(5) N N1 FE N2 C8 . . . . -177.2(6) N N1 FE N2 C8 2_655 . . . -88.0(6) N N2 FE N3 C13 . . . . 173.6(6) N N2 FE N3 C13 2_655 . . . -7.3(6) N N3 FE N3 C13 2_655 . . . 72.2(5) N N1 FE N3 C13 . . . . 171.0(7) N N1 FE N3 C13 2_655 . . . -87.1(6) N N2 FE N3 C9 . . . . -1.0(5) N N2 FE N3 C9 2_655 . . . 178.1(5) N N3 FE N3 C9 2_655 . . . -102.4(5) N N1 FE N3 C9 . . . . -3.6(1) N N1 FE N3 C9 2_655 . . . 98.3(5) N C5 N1 C1 C2 . . . . 0.20(16) N FE N1 C1 C2 . . . . -178.5(1) N N1 C1 C2 C3 . . . . 1(2) N C1 C2 C3 C4 . . . . -2.30(19) N C2 C3 C4 C5 . . . . 3.00(16) N C1 N1 C5 C4 . . . . 0.50(13) N FE N1 C5 C4 . . . . 179.3(7) N C1 N1 C5 C6 . . . . -179.1(8) N FE N1 C5 C6 . . . . -0.3(9) N C3 C4 C5 N1 . . . . -2.20(14) N C3 C4 C5 C6 . . . . 177.5(9) N C7 N4 C6 N2 . . . . 3.1(1) N C7 N4 C6 C5 . . . . -176.7(7) N C8 N2 C6 N4 . . . . -2.1(1) N FE N2 C6 N4 . . . . -177.5(5) N C8 N2 C6 C5 . . . . 177.7(6) N FE N2 C6 C5 . . . . 2.3(8) N N1 C5 C6 N4 . . . . 178.7(7) N C4 C5 C6 N4 . . . . -0.90(13) N N1 C5 C6 N2 . . . . -1.1(9) N C4 C5 C6 N2 . . . . 179.2(8) N C6 N4 C7 N5 . . . . -2.5(1) N C6 N4 C7 C14 . . . . 177.1(6) N C8 N5 C7 N4 . . . . 0.9(1) N C8 N5 C7 C14 . . . . -178.7(6) N C7 N5 C8 N2 . . . . 0.3(1) N C7 N5 C8 C9 . . . . -178.4(6) N C6 N2 C8 N5 . . . . 0.2(1) N FE N2 C8 N5 . . . . 175.7(5) N C6 N2 C8 C9 . . . . 179.1(6) N FE N2 C8 C9 . . . . -5.4(8) N C13 N3 C9 C10 . . . . 0.4(1) N FE N3 C9 C10 . . . . 175.4(6) N C13 N3 C9 C8 . . . . -176.6(6) N FE N3 C9 C8 . . . . -1.5(7) N N5 C8 C9 N3 . . . . -176.9(6) N N2 C8 C9 N3 . . . . 4.2(8) N N5 C8 C9 C10 . . . . 6.10(11) N N2 C8 C9 C10 . . . . -172.8(7) N N3 C9 C10 C11 . . . . -1.50(12) N C8 C9 C10 C11 . . . . 175.2(7) N C9 C10 C11 C12 . . . . 1.90(12) N C10 C11 C12 C13 . . . . -1.20(12) N C9 N3 C13 C12 . . . . 0.4(1) N FE N3 C13 C12 . . . . -174.1(5) N C11 C12 C13 N3 . . . . 0.10(11) N N4 C7 C14 C15 . . . . 162.1(7) N N5 C7 C14 C15 . . . . -18.3(1) N N4 C7 C14 C19 . . . . -19.0(1) N N5 C7 C14 C19 . . . . 160.6(7) N C19 C14 C15 C16 . . . . -2.10(13) N C7 C14 C15 C16 . . . . 176.8(8) N C14 C15 C16 C17 . . . . 2.10(15) N C15 C16 C17 C18 . . . . -2.10(16) N C15 C16 C17 BR1 . . . . 179.1(8) N C16 C17 C18 C19 . . . . 1.90(15) N BR1 C17 C18 C19 . . . . -179.2(6) N C17 C18 C19 C14 . . . . -1.80(13) N C15 C14 C19 C18 . . . . 1.90(12) N C7 C14 C19 C18 . . . . -176.9(7) N F114 P11 F113 F116 . . . . 92.20(18) N F115 P11 F113 F116 . . . . -65(8) N F111 P11 F113 F116 . . . . -169(2) N F112 P11 F113 F116 . . . . -79(2) N F114 P11 F116 F113 . . . . -91.10(15) N F115 P11 F116 F113 . . . . 168(2) N F111 P11 F116 F113 . . . . 39(6) N F112 P11 F116 F113 . . . . 95.10(13) N _diffrn_measured_fraction_theta_max 0.976 _diffrn_reflns_theta_full 73.02 _diffrn_measured_fraction_theta_full 0.976 _refine_diff_density_max 1.439 _refine_diff_density_min -2.241 _refine_diff_density_rms 0.151 # ======================================================== # STRUCTURAL DATA # ======================================================== data_gary61 _database_code_depnum_ccdc_archive 'CCDC 611626' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C38 H24 Br2 Ni N10, 2(F6 P), (C2 H3 N)' _chemical_formula_sum 'C40 H27 Br2 F12 N11 Ni P2' _chemical_formula_weight 1170.20 _chemical_compound_source 'Synthesized by the authors. See text' 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 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.2955 0.4335 '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' Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 _symmetry_space_group_name_hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.5536(2) _cell_length_b 13.6850(2) _cell_length_c 18.9796(3) _cell_angle_alpha 91.0860(10) _cell_angle_beta 102.3480(10) _cell_angle_gamma 91.9730(10) _cell_volume 2168.21(7) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 6288 _cell_measurement_theta_min 2.38 _cell_measurement_theta_max 72.92 _exptl_crystal_description block _exptl_crystal_colour green _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.09 _exptl_crystal_size_min 0.09 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.792 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1160 _exptl_absorpt_coefficient_mu 4.392 _exptl_absorpt_correction_Type multi-scan _exptl_absorpt_correction_T_min 0.6600 _exptl_absorpt_correction_T_max 0.6700 _exptl_absorpt_process_details 'Sadabs (Sheldrick,1996)' _exptl_special_details ; X-ray crystallographic data for I were collected from a single crystal sample, which was mounted on a loop fiber. Data were collected using a Bruker Platform diffractometer, equipped with a Bruker SMART 2K Charged-Coupled Device (CCD) Area Detector using the program SMART and normal focus sealed tube source graphite monochromated Cu-K\a radiation. The crystal-to-detector distance was 4.908 cm, and the data collection was carried out in 512 x 512 pixel mode, utilizing 4 x 4 pixel binning. The initial unit cell parameters were determined by a least-squares fit of the angular setting of strong reflections, collected by a 9.0 degree scan in 30 frames over four different parts of the reciprocal space (120 frames total). One complete sphere of data was collected, to better than 0.8\%A resolution. Upon completion of the data collection, the first 101 frames were recollected in order to improve the decay correction analysis. ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'X-ray Sealed Tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Smart 2000' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 5.5 _diffrn_standards_number 5 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0.00 _diffrn_reflns_number 26398 _diffrn_reflns_av_R_equivalents 0.052 _diffrn_reflns_av_sigmaI/netI 0.0829 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 2.38 _diffrn_reflns_theta_max 73.11 _reflns_number_total 8310 _reflns_number_gt 5242 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'SMART (Bruker, 1999)' _computing_cell_refinement 'SMART (Bruker, 1999)' _computing_data_reduction 'SAINT (Bruker, 1999)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL (Bruker, 1997)' _computing_publication_material 'UdMX (local program)' _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^)+(0.0726P)^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_extinction_coef ? _refine_ls_number_reflns 8310 _refine_ls_number_parameters 666 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0893 _refine_ls_R_factor_gt 0.0528 _refine_ls_wR_factor_ref 0.1338 _refine_ls_wR_factor_gt 0.1216 _refine_ls_goodness_of_fit_ref 0.910 _refine_ls_restrained_S_all 0.909 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Ni Ni 0.80346(9) 0.74084(5) 0.75813(4) 0.01702(18) Uani 1 1 d . . . N1 N 1.0083(4) 0.6890(3) 0.72254(18) 0.0164(8) Uani 1 1 d . . . N2 N 0.7467(4) 0.7588(3) 0.65263(18) 0.0195(8) Uani 1 1 d . . . N3 N 0.5755(4) 0.8086(3) 0.74101(19) 0.0165(8) Uani 1 1 d . . . N5 N 0.5734(5) 0.8169(3) 0.5508(2) 0.0255(9) Uani 1 1 d . . . N4 N 0.8108(5) 0.7365(3) 0.53845(19) 0.0253(9) Uani 1 1 d . . . N6 N 0.7106(4) 0.5943(3) 0.76787(18) 0.0173(8) Uani 1 1 d . . . N7 N 0.8559(4) 0.7210(3) 0.86403(19) 0.0196(8) Uani 1 1 d . . . N8 N 0.9212(4) 0.8778(3) 0.80254(19) 0.0175(8) Uani 1 1 d . . . N10 N 0.9665(4) 0.7808(3) 0.98207(18) 0.0173(8) Uani 1 1 d . . . N9 N 0.8427(4) 0.6197(3) 0.96112(18) 0.0185(8) Uani 1 1 d . . . C1 C 1.1433(5) 0.6584(3) 0.7626(2) 0.0204(10) Uani 1 1 d . . . H1 H 1.1570 0.6612 0.8136 0.024 Uiso 1 1 calc R . . C2 C 1.2656(6) 0.6224(3) 0.7329(2) 0.0254(11) Uani 1 1 d . . . H2 H 1.3618 0.6022 0.7631 0.031 Uiso 1 1 calc R . . C3 C 1.2447(6) 0.6166(4) 0.6587(2) 0.0285(12) Uani 1 1 d . . . H3 H 1.3251 0.5900 0.6372 0.034 Uiso 1 1 calc R . . C4 C 1.1067(6) 0.6496(4) 0.6163(2) 0.0288(12) Uani 1 1 d . . . H4 H 1.0915 0.6476 0.5652 0.035 Uiso 1 1 calc R . . C5 C 0.9902(6) 0.6860(3) 0.6492(2) 0.0202(10) Uani 1 1 d . . . C6 C 0.8423(5) 0.7279(3) 0.6091(2) 0.0198(10) Uani 1 1 d . . . C7 C 0.6753(6) 0.7819(4) 0.5107(2) 0.0252(11) Uani 1 1 d . . . C8 C 0.6145(6) 0.8017(3) 0.6201(2) 0.0207(10) Uani 1 1 d . . . C9 C 0.5169(5) 0.8341(3) 0.6720(2) 0.0191(10) Uani 1 1 d . . . C10 C 0.3789(6) 0.8850(4) 0.6501(3) 0.0287(12) Uani 1 1 d . . . H10 H 0.3424 0.9009 0.6010 0.034 Uiso 1 1 calc R . . C11 C 0.2944(6) 0.9125(4) 0.7025(3) 0.0312(12) Uani 1 1 d . . . H11 H 0.2004 0.9490 0.6904 0.037 Uiso 1 1 calc R . . C12 C 0.3528(6) 0.8845(3) 0.7724(3) 0.0275(12) Uani 1 1 d . . . H12 H 0.2959 0.8998 0.8088 0.033 Uiso 1 1 calc R . . C13 C 0.4931(6) 0.8345(3) 0.7902(2) 0.0211(10) Uani 1 1 d . . . H13 H 0.5320 0.8182 0.8391 0.025 Uiso 1 1 calc R . . C14 C 0.6339(6) 0.7977(4) 0.4331(2) 0.0245(11) Uani 1 1 d . . . C15 C 0.7269(6) 0.7575(4) 0.3877(2) 0.0311(13) Uani 1 1 d . . . H15 H 0.8142 0.7181 0.4072 0.037 Uiso 1 1 calc R . . C16 C 0.6910(6) 0.7755(4) 0.3149(2) 0.0310(12) Uani 1 1 d . . . H16 H 0.7534 0.7483 0.2842 0.037 Uiso 1 1 calc R . . C17 C 0.5659(6) 0.8322(4) 0.2870(2) 0.0275(12) Uani 1 1 d . . . C18 C 0.4710(7) 0.8720(4) 0.3303(3) 0.0369(14) Uani 1 1 d . . . H18 H 0.3829 0.9104 0.3101 0.044 Uiso 1 1 calc R . . C19 C 0.5071(6) 0.8547(4) 0.4029(3) 0.0339(13) Uani 1 1 d . . . H19 H 0.4437 0.8823 0.4330 0.041 Uiso 1 1 calc R . . Br1 Br 0.51660(7) 0.85586(4) 0.18669(3) 0.03590(17) Uani 1 1 d . . . C21 C 0.6348(5) 0.5313(3) 0.7156(2) 0.0193(10) Uani 1 1 d . . . H21 H 0.6275 0.5484 0.6667 0.023 Uiso 1 1 calc R . . C22 C 0.5674(6) 0.4432(3) 0.7295(2) 0.0245(11) Uani 1 1 d . . . H22 H 0.5146 0.4007 0.6909 0.029 Uiso 1 1 calc R . . C23 C 0.5771(6) 0.4164(3) 0.8012(2) 0.0247(11) Uani 1 1 d . . . H23 H 0.5284 0.3567 0.8121 0.030 Uiso 1 1 calc R . . C24 C 0.6601(6) 0.4797(3) 0.8560(2) 0.0226(11) Uani 1 1 d . . . H24 H 0.6719 0.4634 0.9052 0.027 Uiso 1 1 calc R . . C25 C 0.7241(5) 0.5657(3) 0.8372(2) 0.0164(10) Uani 1 1 d . . . C26 C 0.8117(5) 0.6385(3) 0.8916(2) 0.0166(10) Uani 1 1 d . . . C27 C 0.9203(5) 0.6943(3) 1.0046(2) 0.0194(10) Uani 1 1 d . . . C28 C 0.9326(5) 0.7899(3) 0.9110(2) 0.0167(9) Uani 1 1 d . . . C29 C 0.9740(5) 0.8797(3) 0.8756(2) 0.0189(10) Uani 1 1 d . . . C30 C 1.0570(5) 0.9596(3) 0.9138(2) 0.0217(10) Uani 1 1 d . . . H30 H 1.0933 0.9582 0.9647 0.026 Uiso 1 1 calc R . . C31 C 1.0858(6) 1.0413(3) 0.8762(3) 0.0262(11) Uani 1 1 d . . . H31 H 1.1429 1.0970 0.9009 0.031 Uiso 1 1 calc R . . C32 C 1.0306(6) 1.0411(3) 0.8022(2) 0.0234(11) Uani 1 1 d . . . H32 H 1.0480 1.0968 0.7754 0.028 Uiso 1 1 calc R . . C33 C 0.9489(6) 0.9576(3) 0.7678(2) 0.0218(10) Uani 1 1 d . . . H33 H 0.9112 0.9578 0.7169 0.026 Uiso 1 1 calc R . . C34 C 0.9537(5) 0.6771(3) 1.0825(2) 0.0180(10) Uani 1 1 d . . . C35 C 0.8656(6) 0.6049(4) 1.1094(3) 0.0292(12) Uani 1 1 d . . . H35 H 0.7847 0.5670 1.0773 0.035 Uiso 1 1 calc R . . C36 C 0.8953(6) 0.5880(4) 1.1827(3) 0.0304(12) Uani 1 1 d . . . H36 H 0.8343 0.5395 1.2013 0.036 Uiso 1 1 calc R . . C37 C 1.0169(6) 0.6437(4) 1.2287(2) 0.0291(12) Uani 1 1 d . . . C38 C 1.1061(6) 0.7155(4) 1.2031(2) 0.0271(12) Uani 1 1 d . . . H38 H 1.1878 0.7527 1.2353 0.033 Uiso 1 1 calc R . . C39 C 1.0743(6) 0.7323(3) 1.1296(2) 0.0238(11) Uani 1 1 d . . . H39 H 1.1346 0.7814 1.1112 0.029 Uiso 1 1 calc R . . Br2 Br 1.06294(8) 0.61520(5) 1.32809(3) 0.04438(19) Uani 1 1 d . . . P1 P 0.0688(3) 0.9787(2) 0.44233(15) 0.0331(7) Uani 0.50 1 d P A -1 F11 F -0.0056(10) 0.9240(5) 0.3654(4) 0.0438(19) Uani 0.50 1 d P A -1 F12 F 0.2306(8) 0.9916(5) 0.4170(4) 0.0544(19) Uani 0.50 1 d P A -1 F13 F 0.0220(7) 1.0825(4) 0.4066(3) 0.0379(15) Uani 0.50 1 d P A -1 F14 F 0.1147(9) 0.8754(5) 0.4756(4) 0.059(2) Uani 0.50 1 d P A -1 F15 F 0.1172(5) 1.0317(3) 0.5270(2) 0.0823(14) Uani 1 1 d . A -1 P2 P 0.40218(16) 0.70290(10) 0.96750(6) 0.0257(3) Uani 1 1 d . . . F21 F 0.2352(3) 0.6421(2) 0.95430(17) 0.0421(8) Uani 1 1 d . . . F22 F 0.4417(3) 0.6495(2) 0.89765(15) 0.0375(8) Uani 1 1 d . . . F23 F 0.3140(3) 0.7865(2) 0.91617(15) 0.0346(7) Uani 1 1 d . . . F24 F 0.3611(4) 0.7583(3) 1.03531(16) 0.0627(11) Uani 1 1 d . . . F25 F 0.4891(4) 0.6203(3) 1.01649(17) 0.0561(10) Uani 1 1 d . . . F26 F 0.5680(4) 0.7652(2) 0.97768(17) 0.0461(9) Uani 1 1 d . . . P3 P 0.5000 0.5000 0.5000 0.0401(6) Uani 1 2 d S . . F31 F 0.5582(4) 0.5591(2) 0.43804(15) 0.0570(10) Uani 1 1 d . . . F32 F 0.3183(4) 0.5095(3) 0.45972(18) 0.0655(11) Uani 1 1 d . . . F33 F 0.5055(4) 0.3996(2) 0.45515(16) 0.0562(10) Uani 1 1 d . . . C41 C 0.503(6) 0.004(4) -0.0132(12) 0.044(7) Uani 0.50 1 d P B -1 H41A H 0.5829 0.0586 -0.0072 0.065 Uiso 0.50 1 calc PR B -1 H41B H 0.4400 0.0021 -0.0629 0.065 Uiso 0.50 1 calc PR B -1 H41C H 0.5569 -0.0573 -0.0029 0.065 Uiso 0.50 1 calc PR B -1 C42 C 0.3979(15) 0.0189(8) 0.0360(6) 0.034(3) Uani 0.50 1 d P B -1 N43 N 0.3115(12) 0.0291(8) 0.0734(5) 0.047(3) Uani 0.50 1 d P B -1 C51 C 0.1521(15) 0.7989(9) 0.4744(6) 0.045(3) Uani 0.50 1 d PD C -2 H51A H 0.1005 0.8271 0.5110 0.068 Uiso 0.50 1 calc PR C -2 H51B H 0.2681 0.7987 0.4932 0.068 Uiso 0.50 1 calc PR C -2 H51C H 0.1103 0.7317 0.4623 0.068 Uiso 0.50 1 calc PR C -2 C52 C 0.1194(16) 0.8556(11) 0.4115(7) 0.059(4) Uani 0.50 1 d PD C -2 N53 N 0.0951(17) 0.9064(12) 0.3622(8) 0.086(5) Uani 0.50 1 d PD C -2 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Ni 0.0214(5) 0.0196(4) 0.0112(4) -0.0004(3) 0.0055(3) 0.0036(3) N1 0.021(2) 0.014(2) 0.0146(18) -0.0030(15) 0.0059(15) 0.0031(15) N2 0.021(2) 0.025(2) 0.0136(19) 0.0029(16) 0.0055(15) 0.0038(17) N3 0.017(2) 0.016(2) 0.0185(19) 0.0002(15) 0.0062(15) 0.0042(15) N5 0.024(3) 0.036(3) 0.018(2) 0.0079(18) 0.0063(17) 0.0054(18) N4 0.023(2) 0.039(3) 0.0144(19) 0.0050(18) 0.0039(16) 0.0053(18) N6 0.021(2) 0.019(2) 0.0125(18) -0.0034(15) 0.0045(15) 0.0027(16) N7 0.024(2) 0.019(2) 0.016(2) -0.0025(16) 0.0060(16) 0.0001(16) N8 0.021(2) 0.017(2) 0.0156(19) -0.0018(15) 0.0055(15) 0.0029(15) N10 0.021(2) 0.017(2) 0.0152(19) 0.0013(15) 0.0053(15) 0.0025(15) N9 0.024(2) 0.019(2) 0.0129(18) -0.0032(15) 0.0061(15) 0.0015(16) C1 0.025(3) 0.019(2) 0.017(2) -0.0023(19) 0.0036(19) 0.0027(19) C2 0.024(3) 0.028(3) 0.024(3) -0.002(2) 0.003(2) 0.008(2) C3 0.025(3) 0.040(3) 0.022(3) -0.009(2) 0.008(2) 0.010(2) C4 0.028(3) 0.045(3) 0.015(2) -0.005(2) 0.009(2) 0.010(2) C5 0.024(3) 0.028(3) 0.008(2) -0.0052(18) 0.0016(18) 0.004(2) C6 0.019(3) 0.028(3) 0.015(2) 0.0013(19) 0.0082(18) 0.002(2) C7 0.024(3) 0.032(3) 0.021(3) 0.003(2) 0.006(2) -0.002(2) C8 0.019(3) 0.024(3) 0.019(2) 0.004(2) 0.0039(19) 0.0033(19) C9 0.023(3) 0.018(2) 0.017(2) 0.0003(18) 0.0058(19) 0.0011(19) C10 0.031(3) 0.031(3) 0.027(3) 0.010(2) 0.012(2) 0.011(2) C11 0.027(3) 0.029(3) 0.042(3) 0.005(2) 0.017(2) 0.010(2) C12 0.031(3) 0.024(3) 0.032(3) -0.004(2) 0.016(2) -0.001(2) C13 0.023(3) 0.022(3) 0.021(2) -0.004(2) 0.0109(19) 0.000(2) C14 0.023(3) 0.037(3) 0.013(2) 0.007(2) 0.0029(19) -0.001(2) C15 0.025(3) 0.052(4) 0.016(2) 0.005(2) 0.003(2) 0.007(2) C16 0.036(3) 0.042(3) 0.016(2) -0.004(2) 0.008(2) -0.003(2) C17 0.036(3) 0.025(3) 0.019(3) 0.006(2) 0.002(2) -0.009(2) C18 0.046(4) 0.042(3) 0.022(3) 0.009(2) 0.002(2) 0.013(3) C19 0.039(4) 0.044(3) 0.021(3) 0.009(2) 0.007(2) 0.014(3) Br1 0.0593(4) 0.0321(3) 0.0124(3) 0.0027(2) 0.0011(2) -0.0112(3) C21 0.022(3) 0.019(2) 0.016(2) -0.0017(18) 0.0024(18) 0.0067(19) C22 0.029(3) 0.020(3) 0.023(3) -0.004(2) 0.002(2) 0.004(2) C23 0.036(3) 0.014(2) 0.023(3) -0.004(2) 0.004(2) -0.001(2) C24 0.030(3) 0.024(3) 0.016(2) -0.0007(19) 0.0089(19) 0.003(2) C25 0.024(3) 0.018(2) 0.009(2) -0.0006(17) 0.0052(17) 0.0075(19) C26 0.021(3) 0.019(2) 0.011(2) 0.0000(18) 0.0044(17) 0.0069(19) C27 0.023(3) 0.026(3) 0.010(2) 0.0004(19) 0.0035(18) 0.008(2) C28 0.017(3) 0.018(2) 0.016(2) -0.0034(18) 0.0029(17) 0.0040(18) C29 0.021(3) 0.019(2) 0.017(2) -0.0024(19) 0.0059(18) 0.0019(19) C30 0.025(3) 0.023(3) 0.017(2) -0.0053(19) 0.0058(19) 0.002(2) C31 0.032(3) 0.022(3) 0.025(3) -0.007(2) 0.010(2) -0.001(2) C32 0.031(3) 0.018(3) 0.025(3) 0.005(2) 0.013(2) 0.007(2) C33 0.027(3) 0.023(3) 0.017(2) 0.0017(19) 0.0083(19) 0.006(2) C34 0.021(3) 0.023(3) 0.010(2) 0.0021(18) 0.0040(17) 0.0076(19) C35 0.036(3) 0.029(3) 0.023(3) 0.003(2) 0.006(2) 0.002(2) C36 0.041(3) 0.032(3) 0.021(3) 0.007(2) 0.013(2) 0.003(2) C37 0.036(3) 0.039(3) 0.015(2) 0.006(2) 0.009(2) 0.020(2) C38 0.030(3) 0.034(3) 0.016(2) -0.005(2) 0.001(2) 0.011(2) C39 0.029(3) 0.025(3) 0.017(2) -0.004(2) 0.004(2) 0.006(2) Br2 0.0560(4) 0.0668(5) 0.0140(3) 0.0097(3) 0.0110(2) 0.0285(3) P1 0.0317(17) 0.0271(15) 0.0345(16) 0.0018(12) -0.0057(12) -0.0031(12) F11 0.063(6) 0.037(4) 0.029(4) -0.001(3) 0.007(4) -0.009(4) F12 0.053(5) 0.038(4) 0.077(5) -0.014(4) 0.028(4) 0.000(3) F13 0.054(4) 0.026(3) 0.029(3) 0.004(3) -0.001(3) -0.004(3) F14 0.069(5) 0.039(4) 0.054(5) 0.013(4) -0.022(4) 0.000(4) F15 0.096(3) 0.049(3) 0.080(3) -0.009(2) -0.030(2) 0.000(2) P2 0.0272(8) 0.0357(8) 0.0149(6) -0.0018(5) 0.0057(5) 0.0058(6) F21 0.032(2) 0.0397(19) 0.058(2) 0.0043(16) 0.0164(15) 0.0006(14) F22 0.043(2) 0.0429(19) 0.0289(16) -0.0094(14) 0.0113(13) 0.0140(15) F23 0.0370(19) 0.0347(18) 0.0346(17) 0.0035(14) 0.0115(14) 0.0130(14) F24 0.050(2) 0.110(3) 0.0257(18) -0.0305(19) 0.0049(15) 0.022(2) F25 0.043(2) 0.088(3) 0.043(2) 0.033(2) 0.0165(16) 0.0224(19) F26 0.029(2) 0.045(2) 0.063(2) -0.0153(17) 0.0085(16) 0.0023(15) P3 0.0528(15) 0.0520(14) 0.0125(9) -0.0017(9) 0.0043(9) -0.0222(11) F31 0.086(3) 0.065(2) 0.0190(16) -0.0017(16) 0.0155(16) -0.035(2) F32 0.056(3) 0.094(3) 0.040(2) 0.002(2) -0.0004(17) -0.016(2) F33 0.088(3) 0.055(2) 0.0270(18) -0.0064(16) 0.0197(17) -0.025(2) C41 0.049(8) 0.032(10) 0.042(19) -0.009(17) -0.005(18) 0.001(6) C42 0.035(8) 0.026(6) 0.032(7) 0.001(5) -0.011(5) -0.001(5) N43 0.042(7) 0.062(7) 0.032(6) -0.012(5) -0.005(5) 0.007(5) C51 0.055(9) 0.050(8) 0.035(7) -0.006(6) 0.021(6) -0.009(7) C52 0.047(9) 0.096(12) 0.035(7) 0.022(8) 0.009(6) 0.006(8) N53 0.071(12) 0.126(14) 0.069(10) 0.056(9) 0.027(9) 0.011(10) _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_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag Ni N2 . . 1.979(3) Y Ni N7 . . 1.989(4) Y Ni N1 . . 2.146(4) Y Ni N3 . . 2.152(4) Y Ni N6 . . 2.157(4) Y Ni N8 . . 2.164(4) Y N1 C1 . . 1.325(5) Y N1 C5 . . 1.367(5) Y N2 C8 . . 1.328(5) Y N2 C6 . . 1.352(5) Y N3 C13 . . 1.335(5) Y N3 C9 . . 1.356(5) Y N5 C8 . . 1.310(5) Y N5 C7 . . 1.366(6) Y N4 C6 . . 1.319(5) Y N4 C7 . . 1.345(6) Y N6 C21 . . 1.343(5) Y N6 C25 . . 1.363(5) Y N7 C26 . . 1.330(5) Y N7 C28 . . 1.338(5) Y N8 C33 . . 1.327(5) Y N8 C29 . . 1.363(5) Y N10 C28 . . 1.327(5) Y N10 C27 . . 1.342(5) Y N9 C26 . . 1.320(5) Y N9 C27 . . 1.361(5) Y C1 C2 . . 1.390(6) Y C1 H1 . . 0.95 ? C2 C3 . . 1.382(6) Y C2 H2 . . 0.95 ? C3 C4 . . 1.375(6) Y C3 H3 . . 0.95 ? C4 C5 . . 1.386(6) Y C4 H4 . . 0.95 ? C5 C6 . . 1.470(6) Y C7 C14 . . 1.460(6) Y C8 C9 . . 1.491(6) Y C9 C10 . . 1.381(6) Y C10 C11 . . 1.402(6) Y C10 H10 . . 0.95 ? C11 C12 . . 1.380(7) Y C11 H11 . . 0.95 ? C12 C13 . . 1.383(6) Y C12 H12 . . 0.95 ? C13 H13 . . 0.95 ? C14 C19 . . 1.386(6) Y C14 C15 . . 1.409(6) Y C15 C16 . . 1.378(6) Y C15 H15 . . 0.95 ? C16 C17 . . 1.363(7) Y C16 H16 . . 0.95 ? C17 C18 . . 1.390(7) Y C17 Br1 . . 1.896(5) Y C18 C19 . . 1.372(6) Y C18 H18 . . 0.95 ? C19 H19 . . 0.95 ? C21 C22 . . 1.374(6) Y C21 H21 . . 0.95 ? C22 C23 . . 1.401(6) Y C22 H22 . . 0.95 ? C23 C24 . . 1.394(6) Y C23 H23 . . 0.95 ? C24 C25 . . 1.366(6) Y C24 H24 . . 0.95 ? C25 C26 . . 1.483(6) Y C27 C34 . . 1.469(5) Y C28 C29 . . 1.479(6) Y C29 C30 . . 1.386(6) Y C30 C31 . . 1.380(6) Y C30 H30 . . 0.95 ? C31 C32 . . 1.381(6) Y C31 H31 . . 0.95 ? C32 C33 . . 1.394(6) Y C32 H32 . . 0.95 ? C33 H33 . . 0.95 ? C34 C35 . . 1.391(6) Y C34 C39 . . 1.400(6) Y C35 C36 . . 1.385(6) Y C35 H35 . . 0.95 ? C36 C37 . . 1.399(7) Y C36 H36 . . 0.95 ? C37 C38 . . 1.381(7) Y C37 Br2 . . 1.893(4) Y C38 C39 . . 1.389(6) Y C38 H38 . . 0.95 ? C39 H39 . . 0.95 ? P1 F12 . . 1.564(7) Y P1 F14 . . 1.586(7) Y P1 F13 . . 1.612(6) Y P1 F11 . . 1.620(7) Y P1 F15 . . 1.712(5) Y P2 F25 . . 1.580(3) Y P2 F24 . . 1.591(3) Y P2 F21 . . 1.598(3) Y P2 F26 . . 1.602(3) Y P2 F22 . . 1.606(3) Y P2 F23 . . 1.617(3) Y P3 F32 . . 1.590(4) Y P3 F32 . 2_666 1.590(4) Y P3 F31 . . 1.595(3) Y P3 F31 . 2_666 1.595(3) Y P3 F33 . . 1.610(3) Y P3 F33 . 2_666 1.610(3) Y C41 C42 . . 1.44(4) Y C41 H41a . . 0.98 ? C41 H41b . . 0.98 ? C41 H41c . . 0.98 ? C42 N43 . . 1.139(14) Y C51 C52 . . 1.418(12) Y C51 H51a . . 0.98 ? C51 H51b . . 0.98 ? C51 H51c . . 0.98 ? C52 N53 . . 1.164(13) Y loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_2 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag N2 NI N7 . . . 178.68(16) Y N2 NI N1 . . . 76.97(14) Y N7 NI N1 . . . 103.78(14) Y N2 NI N3 . . . 76.07(14) Y N7 NI N3 . . . 103.22(15) Y N1 NI N3 . . . 152.90(14) Y N2 NI N6 . . . 102.18(15) Y N7 NI N6 . . . 76.74(14) Y N1 NI N6 . . . 92.46(13) Y N3 NI N6 . . . 95.85(14) Y N2 NI N8 . . . 105.00(15) Y N7 NI N8 . . . 76.07(14) Y N1 NI N8 . . . 94.43(14) Y N3 NI N8 . . . 89.85(14) Y N6 NI N8 . . . 152.81(13) Y C1 N1 C5 . . . 118.4(4) Y C1 N1 NI . . . 127.9(3) Y C5 N1 NI . . . 113.6(3) Y C8 N2 C6 . . . 115.8(4) Y C8 N2 NI . . . 122.8(3) Y C6 N2 NI . . . 121.3(3) Y C13 N3 C9 . . . 117.2(4) Y C13 N3 NI . . . 128.1(3) Y C9 N3 NI . . . 114.5(3) Y C8 N5 C7 . . . 115.2(4) Y C6 N4 C7 . . . 115.2(4) Y C21 N6 C25 . . . 116.9(4) Y C21 N6 NI . . . 128.8(3) Y C25 N6 NI . . . 114.2(3) Y C26 N7 C28 . . . 116.7(4) Y C26 N7 NI . . . 121.0(3) Y C28 N7 NI . . . 122.3(3) Y C33 N8 C29 . . . 117.4(4) Y C33 N8 NI . . . 128.3(3) Y C29 N8 NI . . . 114.3(3) Y C28 N10 C27 . . . 114.5(4) Y C26 N9 C27 . . . 114.4(4) Y N1 C1 C2 . . . 122.6(4) Y N1 C1 H1 . . . 118.7 ? C2 C1 H1 . . . 118.7 ? C3 C2 C1 . . . 118.8(4) Y C3 C2 H2 . . . 120.6 ? C1 C2 H2 . . . 120.6 ? C4 C3 C2 . . . 119.4(4) Y C4 C3 H3 . . . 120.3 ? C2 C3 H3 . . . 120.3 ? C3 C4 C5 . . . 119.0(4) Y C3 C4 H4 . . . 120.5 ? C5 C4 H4 . . . 120.5 ? N1 C5 C4 . . . 121.7(4) Y N1 C5 C6 . . . 114.9(4) Y C4 C5 C6 . . . 123.3(4) Y N4 C6 N2 . . . 124.5(4) Y N4 C6 C5 . . . 122.7(4) Y N2 C6 C5 . . . 112.8(4) Y N4 C7 N5 . . . 124.1(4) Y N4 C7 C14 . . . 119.0(4) Y N5 C7 C14 . . . 116.9(4) Y N5 C8 N2 . . . 125.1(4) Y N5 C8 C9 . . . 122.6(4) Y N2 C8 C9 . . . 112.3(4) Y N3 C9 C10 . . . 124.1(4) Y N3 C9 C8 . . . 114.0(4) Y C10 C9 C8 . . . 121.9(4) Y C9 C10 C11 . . . 118.1(5) Y C9 C10 H10 . . . 121 ? C11 C10 H10 . . . 121 ? C12 C11 C10 . . . 117.5(5) Y C12 C11 H11 . . . 121.2 ? C10 C11 H11 . . . 121.2 ? C11 C12 C13 . . . 120.9(4) Y C11 C12 H12 . . . 119.5 ? C13 C12 H12 . . . 119.5 ? N3 C13 C12 . . . 122.1(4) Y N3 C13 H13 . . . 118.9 ? C12 C13 H13 . . . 118.9 ? C19 C14 C15 . . . 118.6(4) Y C19 C14 C7 . . . 121.4(5) Y C15 C14 C7 . . . 120.0(4) Y C16 C15 C14 . . . 119.9(5) Y C16 C15 H15 . . . 120.1 ? C14 C15 H15 . . . 120.1 ? C17 C16 C15 . . . 120.1(5) Y C17 C16 H16 . . . 120 ? C15 C16 H16 . . . 120 ? C16 C17 C18 . . . 121.3(5) Y C16 C17 BR1 . . . 119.8(4) Y C18 C17 BR1 . . . 118.9(4) Y C19 C18 C17 . . . 118.7(5) Y C19 C18 H18 . . . 120.6 ? C17 C18 H18 . . . 120.6 ? C18 C19 C14 . . . 121.5(5) Y C18 C19 H19 . . . 119.3 ? C14 C19 H19 . . . 119.3 ? N6 C21 C22 . . . 122.9(4) Y N6 C21 H21 . . . 118.5 ? C22 C21 H21 . . . 118.5 ? C21 C22 C23 . . . 119.5(4) Y C21 C22 H22 . . . 120.3 ? C23 C22 H22 . . . 120.3 ? C24 C23 C22 . . . 118.1(4) Y C24 C23 H23 . . . 120.9 ? C22 C23 H23 . . . 120.9 ? C25 C24 C23 . . . 118.5(4) Y C25 C24 H24 . . . 120.7 ? C23 C24 H24 . . . 120.7 ? N6 C25 C24 . . . 124.0(4) Y N6 C25 C26 . . . 113.6(4) Y C24 C25 C26 . . . 122.4(4) Y N9 C26 N7 . . . 124.5(4) Y N9 C26 C25 . . . 121.1(4) Y N7 C26 C25 . . . 114.3(4) Y N10 C27 N9 . . . 125.4(4) Y N10 C27 C34 . . . 118.5(4) Y N9 C27 C34 . . . 116.1(4) Y N10 C28 N7 . . . 124.4(4) Y N10 C28 C29 . . . 122.7(4) Y N7 C28 C29 . . . 113.0(4) Y N8 C29 C30 . . . 122.9(4) Y N8 C29 C28 . . . 114.3(4) Y C30 C29 C28 . . . 122.8(4) Y C31 C30 C29 . . . 118.5(4) Y C31 C30 H30 . . . 120.7 ? C29 C30 H30 . . . 120.7 ? C30 C31 C32 . . . 119.2(4) Y C30 C31 H31 . . . 120.4 ? C32 C31 H31 . . . 120.4 ? C31 C32 C33 . . . 118.7(4) Y C31 C32 H32 . . . 120.6 ? C33 C32 H32 . . . 120.6 ? N8 C33 C32 . . . 123.2(4) Y N8 C33 H33 . . . 118.4 ? C32 C33 H33 . . . 118.4 ? C35 C34 C39 . . . 119.9(4) Y C35 C34 C27 . . . 119.7(4) Y C39 C34 C27 . . . 120.4(4) Y C36 C35 C34 . . . 120.4(5) Y C36 C35 H35 . . . 119.8 ? C34 C35 H35 . . . 119.8 ? C35 C36 C37 . . . 118.8(5) Y C35 C36 H36 . . . 120.6 ? C37 C36 H36 . . . 120.6 ? C38 C37 C36 . . . 121.8(4) Y C38 C37 BR2 . . . 120.0(4) Y C36 C37 BR2 . . . 118.2(4) Y C37 C38 C39 . . . 118.9(5) Y C37 C38 H38 . . . 120.5 ? C39 C38 H38 . . . 120.5 ? C38 C39 C34 . . . 120.3(5) Y C38 C39 H39 . . . 119.9 ? C34 C39 H39 . . . 119.9 ? F12 P1 F14 . . . 92.5(4) Y F12 P1 F13 . . . 87.0(4) Y F14 P1 F13 . . . 178.6(4) Y F12 P1 F11 . . . 87.9(4) Y F14 P1 F11 . . . 89.1(4) Y F13 P1 F11 . . . 89.6(3) Y F12 P1 F15 . . . 101.6(3) Y F14 P1 F15 . . . 89.9(3) Y F13 P1 F15 . . . 91.5(3) Y F11 P1 F15 . . . 170.4(4) Y F25 P2 F24 . . . 91.72(19) Y F25 P2 F21 . . . 91.27(18) Y F24 P2 F21 . . . 90.58(19) Y F25 P2 F26 . . . 90.43(18) Y F24 P2 F26 . . . 90.68(19) Y F21 P2 F26 . . . 177.86(19) Y F25 P2 F22 . . . 89.89(18) Y F24 P2 F22 . . . 178.4(2) Y F21 P2 F22 . . . 89.54(17) Y F26 P2 F22 . . . 89.16(17) Y F25 P2 F23 . . . 179.02(19) Y F24 P2 F23 . . . 89.27(18) Y F21 P2 F23 . . . 88.76(16) Y F26 P2 F23 . . . 89.52(17) Y F22 P2 F23 . . . 89.13(15) Y F32 P3 F32 . . 2_666 179.999(1) Y F32 P3 F31 . . . 90.53(18) Y F32 P3 F31 2_666 . . 89.47(18) Y F32 P3 F31 . . 2_666 89.47(18) Y F32 P3 F31 2_666 . 2_666 90.53(18) Y F31 P3 F31 . . 2_666 179.998(2) Y F32 P3 F33 . . . 89.28(19) Y F32 P3 F33 2_666 . . 90.72(19) Y F31 P3 F33 . . . 89.52(16) Y F31 P3 F33 2_666 . . 90.48(16) Y F32 P3 F33 . . 2_666 90.72(19) Y F32 P3 F33 2_666 . 2_666 89.28(19) Y F31 P3 F33 . . 2_666 90.48(16) Y F31 P3 F33 2_666 . 2_666 89.52(16) Y F33 P3 F33 . . 2_666 179.997(1) Y N43 C42 C41 . . . 178(2) Y C52 C51 H51A . . . 109.5 ? C52 C51 H51B . . . 109.5 ? H51A C51 H51B . . . 109.5 ? C52 C51 H51C . . . 109.5 ? H51A C51 H51C . . . 109.5 ? H51B C51 H51C . . . 109.5 ? N53 C52 C51 . . . 176.50(19) Y loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion _geom_torsion_publ_flag N2 NI N1 C1 . . . . 176.2(4) N N7 NI N1 C1 . . . . -4.9(4) N N3 NI N1 C1 . . . . 170.2(3) N N6 NI N1 C1 . . . . -81.9(4) N N8 NI N1 C1 . . . . 71.8(4) N N2 NI N1 C5 . . . . -5.6(3) N N7 NI N1 C5 . . . . 173.3(3) N N3 NI N1 C5 . . . . -11.6(5) N N6 NI N1 C5 . . . . 96.3(3) N N8 NI N1 C5 . . . . -110.0(3) N N1 NI N2 C8 . . . . -175.1(4) N N3 NI N2 C8 . . . . 2.1(4) N N6 NI N2 C8 . . . . 95.2(4) N N8 NI N2 C8 . . . . -83.9(4) N N1 NI N2 C6 . . . . 4.6(3) N N3 NI N2 C6 . . . . -178.2(4) N N6 NI N2 C6 . . . . -85.1(4) N N8 NI N2 C6 . . . . 95.8(4) N N2 NI N3 C13 . . . . -178.7(4) N N7 NI N3 C13 . . . . 2.5(4) N N1 NI N3 C13 . . . . -172.6(3) N N6 NI N3 C13 . . . . 80.2(4) N N8 NI N3 C13 . . . . -73.2(4) N N2 NI N3 C9 . . . . -4.2(3) N N7 NI N3 C9 . . . . 177.0(3) N N1 NI N3 C9 . . . . 1.9(5) N N6 NI N3 C9 . . . . -105.3(3) N N8 NI N3 C9 . . . . 101.3(3) N N2 NI N6 C21 . . . . 0.5(4) N N7 NI N6 C21 . . . . 179.7(4) N N1 NI N6 C21 . . . . -76.7(4) N N3 NI N6 C21 . . . . 77.4(4) N N8 NI N6 C21 . . . . 178.6(3) N N2 NI N6 C25 . . . . -175.4(3) N N7 NI N6 C25 . . . . 3.8(3) N N1 NI N6 C25 . . . . 107.4(3) N N3 NI N6 C25 . . . . -98.5(3) N N8 NI N6 C25 . . . . 2.7(5) N N1 NI N7 C26 . . . . -91.6(3) N N3 NI N7 C26 . . . . 90.7(3) N N6 NI N7 C26 . . . . -2.3(3) N N8 NI N7 C26 . . . . 177.2(4) N N1 NI N7 C28 . . . . 90.3(4) N N3 NI N7 C28 . . . . -87.4(4) N N6 NI N7 C28 . . . . 179.6(4) N N8 NI N7 C28 . . . . -0.9(3) N N2 NI N8 C33 . . . . 0.7(4) N N7 NI N8 C33 . . . . -178.5(4) N N1 NI N8 C33 . . . . 78.4(4) N N3 NI N8 C33 . . . . -74.8(4) N N6 NI N8 C33 . . . . -177.4(3) N N2 NI N8 C29 . . . . -178.5(3) N N7 NI N8 C29 . . . . 2.3(3) N N1 NI N8 C29 . . . . -100.8(3) N N3 NI N8 C29 . . . . 106.0(3) N N6 NI N8 C29 . . . . 3.4(5) N C5 N1 C1 C2 . . . . -0.9(7) N NI N1 C1 C2 . . . . 177.2(3) N N1 C1 C2 C3 . . . . -1.2(7) N C1 C2 C3 C4 . . . . 2.3(8) N C2 C3 C4 C5 . . . . -1.4(8) N C1 N1 C5 C4 . . . . 1.8(7) N NI N1 C5 C4 . . . . -176.6(4) N C1 N1 C5 C6 . . . . -175.7(4) N NI N1 C5 C6 . . . . 5.9(5) N C3 C4 C5 N1 . . . . -0.6(8) N C3 C4 C5 C6 . . . . 176.6(5) N C7 N4 C6 N2 . . . . 1.8(7) N C7 N4 C6 C5 . . . . -176.0(4) N C8 N2 C6 N4 . . . . -1.1(7) N NI N2 C6 N4 . . . . 179.2(4) N C8 N2 C6 C5 . . . . 176.9(4) N NI N2 C6 C5 . . . . -2.8(5) N N1 C5 C6 N4 . . . . 175.6(4) N C4 C5 C6 N4 . . . . -1.8(8) N N1 C5 C6 N2 . . . . -2.4(6) N C4 C5 C6 N2 . . . . -179.9(5) N C6 N4 C7 N5 . . . . -0.6(7) N C6 N4 C7 C14 . . . . 177.9(4) N C8 N5 C7 N4 . . . . -1.3(7) N C8 N5 C7 C14 . . . . -179.8(4) N C7 N5 C8 N2 . . . . 2.3(7) N C7 N5 C8 C9 . . . . -179.5(4) N C6 N2 C8 N5 . . . . -1.1(7) N NI N2 C8 N5 . . . . 178.6(4) N C6 N2 C8 C9 . . . . -179.6(4) N NI N2 C8 C9 . . . . 0.1(5) N C13 N3 C9 C10 . . . . 0.2(7) N NI N3 C9 C10 . . . . -174.9(4) N C13 N3 C9 C8 . . . . -179.4(4) N NI N3 C9 C8 . . . . 5.5(5) N N5 C8 C9 N3 . . . . 177.7(4) N N2 C8 C9 N3 . . . . -3.8(6) N N5 C8 C9 C10 . . . . -1.9(7) N N2 C8 C9 C10 . . . . 176.5(4) N N3 C9 C10 C11 . . . . 0.3(7) N C8 C9 C10 C11 . . . . 179.9(4) N C9 C10 C11 C12 . . . . -1.6(7) N C10 C11 C12 C13 . . . . 2.5(7) N C9 N3 C13 C12 . . . . 0.6(7) N NI N3 C13 C12 . . . . 175.0(3) N C11 C12 C13 N3 . . . . -2.0(7) N N4 C7 C14 C19 . . . . -171.8(5) N N5 C7 C14 C19 . . . . 6.7(7) N N4 C7 C14 C15 . . . . 6.1(7) N N5 C7 C14 C15 . . . . -175.4(4) N C19 C14 C15 C16 . . . . 0.2(8) N C7 C14 C15 C16 . . . . -177.7(5) N C14 C15 C16 C17 . . . . 0.1(8) N C15 C16 C17 C18 . . . . -0.8(8) N C15 C16 C17 BR1 . . . . -179.6(4) N C16 C17 C18 C19 . . . . 1.2(8) N BR1 C17 C18 C19 . . . . 180.0(4) N C17 C18 C19 C14 . . . . -0.8(8) N C15 C14 C19 C18 . . . . 0.1(8) N C7 C14 C19 C18 . . . . 178.0(5) N C25 N6 C21 C22 . . . . 2.4(6) N NI N6 C21 C22 . . . . -173.4(3) N N6 C21 C22 C23 . . . . -0.1(7) N C21 C22 C23 C24 . . . . -2.0(7) N C22 C23 C24 C25 . . . . 1.7(7) N C21 N6 C25 C24 . . . . -2.7(6) N NI N6 C25 C24 . . . . 173.7(4) N C21 N6 C25 C26 . . . . 179.0(4) N NI N6 C25 C26 . . . . -4.6(5) N C23 C24 C25 N6 . . . . 0.6(7) N C23 C24 C25 C26 . . . . 178.8(4) N C27 N9 C26 N7 . . . . 2.5(6) N C27 N9 C26 C25 . . . . -178.4(4) N C28 N7 C26 N9 . . . . -2.2(7) N NI N7 C26 N9 . . . . 179.6(3) N C28 N7 C26 C25 . . . . 178.7(4) N NI N7 C26 C25 . . . . 0.5(5) N N6 C25 C26 N9 . . . . -176.2(4) N C24 C25 C26 N9 . . . . 5.4(7) N N6 C25 C26 N7 . . . . 2.9(5) N C24 C25 C26 N7 . . . . -175.5(4) N C28 N10 C27 N9 . . . . -0.9(6) N C28 N10 C27 C34 . . . . 179.5(4) N C26 N9 C27 N10 . . . . -0.9(6) N C26 N9 C27 C34 . . . . 178.7(4) N C27 N10 C28 N7 . . . . 1.4(6) N C27 N10 C28 C29 . . . . -180.0(4) N C26 N7 C28 N10 . . . . 0.0(6) N NI N7 C28 N10 . . . . 178.2(3) N C26 N7 C28 C29 . . . . -178.7(4) N NI N7 C28 C29 . . . . -0.5(5) N C33 N8 C29 C30 . . . . -1.5(6) N NI N8 C29 C30 . . . . 177.7(3) N C33 N8 C29 C28 . . . . 177.5(4) N NI N8 C29 C28 . . . . -3.3(5) N N10 C28 C29 N8 . . . . -176.2(4) N N7 C28 C29 N8 . . . . 2.6(6) N N10 C28 C29 C30 . . . . 2.8(7) N N7 C28 C29 C30 . . . . -178.5(4) N N8 C29 C30 C31 . . . . 0.8(7) N C28 C29 C30 C31 . . . . -178.1(4) N C29 C30 C31 C32 . . . . 0.3(7) N C30 C31 C32 C33 . . . . -0.7(7) N C29 N8 C33 C32 . . . . 1.1(7) N NI N8 C33 C32 . . . . -178.1(3) N C31 C32 C33 N8 . . . . 0.0(7) N N10 C27 C34 C35 . . . . 159.1(4) N N9 C27 C34 C35 . . . . -20.5(6) N N10 C27 C34 C39 . . . . -21.3(6) N N9 C27 C34 C39 . . . . 159.1(4) N C39 C34 C35 C36 . . . . 0.7(7) N C27 C34 C35 C36 . . . . -179.7(4) N C34 C35 C36 C37 . . . . -1.0(7) N C35 C36 C37 C38 . . . . 0.8(8) N C35 C36 C37 BR2 . . . . -176.9(4) N C36 C37 C38 C39 . . . . -0.3(7) N BR2 C37 C38 C39 . . . . 177.4(3) N C37 C38 C39 C34 . . . . 0.0(7) N C35 C34 C39 C38 . . . . -0.2(7) N C27 C34 C39 C38 . . . . -179.7(4) N _diffrn_measured_fraction_theta_max 0.956 _diffrn_reflns_theta_full 73.11 _diffrn_measured_fraction_theta_full 0.956 _refine_diff_density_max 1.276 _refine_diff_density_min -0.898 _refine_diff_density_rms 0.115 # Attachment '611627.cif' data_gary71 _database_code_depnum_ccdc_archive 'CCDC 611627' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C38 H24 Br2 Cu N10, 2(F6 P), (C2 H3 N)' _chemical_formula_sum 'C40 H27 Br2 Cu F12 N11 P2' _chemical_formula_weight 1175.03 _chemical_compound_source 'Synthesized by the authors. See text' 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 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu -1.9646 0.5888 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 _symmetry_space_group_name_hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.5175(2) _cell_length_b 13.7974(3) _cell_length_c 18.9148(4) _cell_angle_alpha 89.9110(10) _cell_angle_beta 78.4970(10) _cell_angle_gamma 87.8530(10) _cell_volume 2176.64(8) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 16625 _cell_measurement_theta_min 3.21 _cell_measurement_theta_max 67.83 _exptl_crystal_description block _exptl_crystal_colour green _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.793 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1162 _exptl_absorpt_coefficient_mu 4.440 _exptl_absorpt_correction_Type multi-scan _exptl_absorpt_correction_T_min 0.5100 _exptl_absorpt_correction_T_max 0.8400 _exptl_absorpt_process_details 'Sadabs (Sheldrick,1996)' _exptl_special_details ; X-ray crystallographic data for I were collected from a single crystal sample, which was mounted on a loop fiber. Data were collected using a Bruker Platform diffractometer, equipped with a Bruker SMART 2K Charged-Coupled Device (CCD) Area Detector using the program SMART and normal focus sealed tube source graphite monochromated Cu-K\a radiation. The crystal-to-detector distance was 4.908 cm, and the data collection was carried out in 512 x 512 pixel mode, utilizing 4 x 4 pixel binning. The initial unit cell parameters were determined by a least-squares fit of the angular setting of strong reflections, collected by a 9.0 degree scan in 30 frames over four different parts of the reciprocal space (120 frames total). One complete sphere of data was collected, to better than 0.8\%A resolution. Upon completion of the data collection, the first 101 frames were recollected in order to improve the decay correction analysis. ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'X-ray Sealed Tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Smart 2000' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 5.5 _diffrn_standards_number 190 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0.44 _diffrn_reflns_number 27217 _diffrn_reflns_av_R_equivalents 0.027 _diffrn_reflns_av_sigmaI/netI 0.0225 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 2.38 _diffrn_reflns_theta_max 67.94 _reflns_number_total 7620 _reflns_number_gt 6932 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'SMART (Bruker, 1999)' _computing_cell_refinement 'SMART (Bruker, 1999)' _computing_data_reduction 'SAINT (Bruker, 1999)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL (Bruker, 1997)' _computing_publication_material 'UdMX (local program)' _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^)+(0.0466P)^2^+2.1980P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 7620 _refine_ls_number_parameters 688 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0352 _refine_ls_R_factor_gt 0.0318 _refine_ls_wR_factor_ref 0.0869 _refine_ls_wR_factor_gt 0.0841 _refine_ls_goodness_of_fit_ref 1.027 _refine_ls_restrained_S_all 1.027 _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 Cu Cu 0.69475(4) 0.74496(2) 0.253549(16) 0.02129(9) Uani 1 1 d . . . N1 N 0.9214(2) 0.81408(13) 0.23809(10) 0.0216(4) Uani 1 1 d . . . N2 N 0.7491(2) 0.76091(13) 0.14960(10) 0.0222(4) Uani 1 1 d . . . N3 N 0.4861(2) 0.69545(13) 0.21877(10) 0.0221(4) Uani 1 1 d . . . N4 N 0.9252(2) 0.81663(14) 0.04726(10) 0.0264(4) Uani 1 1 d . . . N5 N 0.6858(2) 0.73825(15) 0.03549(10) 0.0274(4) Uani 1 1 d . . . N6 N 0.7875(2) 0.59002(13) 0.26668(10) 0.0219(4) Uani 1 1 d . . . N7 N 0.6431(2) 0.72278(13) 0.36007(10) 0.0204(4) Uani 1 1 d . . . N8 N 0.5716(2) 0.88864(14) 0.30385(10) 0.0237(4) Uani 1 1 d . . . N9 N 0.6558(2) 0.61942(13) 0.45802(10) 0.0233(4) Uani 1 1 d . . . N10 N 0.5342(2) 0.77810(13) 0.47827(10) 0.0231(4) Uani 1 1 d . . . C1 C 1.0020(3) 0.84184(16) 0.28813(12) 0.0255(5) Uani 1 1 d . . . H1 H 0.9620 0.8263 0.3372 0.031 Uiso 1 1 calc R . . C2 C 1.1419(3) 0.89247(18) 0.27065(14) 0.0318(5) Uani 1 1 d . . . H2 H 1.1967 0.9109 0.3073 0.038 Uiso 1 1 calc R . . C3 C 1.2007(3) 0.9159(2) 0.19977(15) 0.0367(6) Uani 1 1 d . . . H3 H 1.2959 0.9512 0.1870 0.044 Uiso 1 1 calc R . . C4 C 1.1187(3) 0.88723(19) 0.14713(14) 0.0328(6) Uani 1 1 d . . . H4 H 1.1567 0.9021 0.0978 0.039 Uiso 1 1 calc R . . C5 C 0.9813(3) 0.83680(16) 0.16848(12) 0.0233(5) Uani 1 1 d . . . C6 C 0.8834(3) 0.80385(16) 0.11750(12) 0.0229(5) Uani 1 1 d . . . C7 C 0.8231(3) 0.78224(17) 0.00779(13) 0.0275(5) Uani 1 1 d . . . C8 C 0.6534(3) 0.73032(17) 0.10645(12) 0.0246(5) Uani 1 1 d . . . C9 C 0.5032(3) 0.68992(17) 0.14613(12) 0.0252(5) Uani 1 1 d . . . C10 C 0.3882(3) 0.6535(2) 0.11256(13) 0.0356(6) Uani 1 1 d . . . H10 H 0.4047 0.6500 0.0614 0.043 Uiso 1 1 calc R . . C11 C 0.2481(3) 0.6220(2) 0.15525(14) 0.0372(6) Uani 1 1 d . . . H11 H 0.1670 0.5958 0.1339 0.045 Uiso 1 1 calc R . . C12 C 0.2281(3) 0.62908(18) 0.22931(13) 0.0305(5) Uani 1 1 d . . . H12 H 0.1319 0.6091 0.2595 0.037 Uiso 1 1 calc R . . C13 C 0.3499(3) 0.66566(16) 0.25930(12) 0.0253(5) Uani 1 1 d . . . H13 H 0.3359 0.6696 0.3103 0.030 Uiso 1 1 calc R . . C14 C 0.8630(3) 0.79666(18) -0.07039(13) 0.0292(5) Uani 1 1 d . . . C15 C 0.9907(4) 0.8527(2) -0.10061(15) 0.0502(8) Uani 1 1 d . . . H15 H 1.0542 0.8802 -0.0703 0.060 Uiso 1 1 calc R . . C16 C 1.0273(4) 0.8694(2) -0.17381(15) 0.0495(8) Uani 1 1 d . . . H16 H 1.1154 0.9075 -0.1941 0.059 Uiso 1 1 calc R . . C17 C 0.9339(3) 0.82981(18) -0.21693(12) 0.0324(6) Uani 1 1 d . . . C18 C 0.8063(3) 0.7740(2) -0.18896(13) 0.0343(6) Uani 1 1 d . . . H18 H 0.7433 0.7471 -0.2196 0.041 Uiso 1 1 calc R . . C19 C 0.7710(3) 0.7574(2) -0.11522(13) 0.0329(6) Uani 1 1 d . . . H19 H 0.6831 0.7189 -0.0953 0.039 Uiso 1 1 calc R . . Br1 Br 0.98484(4) 0.85156(2) -0.318040(13) 0.04007(9) Uani 1 1 d . . . C21 C 0.8648(3) 0.52652(17) 0.21730(12) 0.0255(5) Uani 1 1 d . . . H21 H 0.8713 0.5409 0.1677 0.031 Uiso 1 1 calc R . . C22 C 0.9360(3) 0.44036(17) 0.23565(13) 0.0302(5) Uani 1 1 d . . . H22 H 0.9908 0.3971 0.1992 0.036 Uiso 1 1 calc R . . C23 C 0.9261(3) 0.41845(17) 0.30768(14) 0.0312(5) Uani 1 1 d . . . H23 H 0.9764 0.3607 0.3214 0.037 Uiso 1 1 calc R . . C24 C 0.8415(3) 0.48196(16) 0.35987(13) 0.0269(5) Uani 1 1 d . . . H24 H 0.8298 0.4680 0.4098 0.032 Uiso 1 1 calc R . . C25 C 0.7750(3) 0.56604(15) 0.33663(12) 0.0212(4) Uani 1 1 d . . . C26 C 0.6869(3) 0.63904(15) 0.38841(12) 0.0211(4) Uani 1 1 d . . . C27 C 0.5799(3) 0.69061(16) 0.50148(12) 0.0225(5) Uani 1 1 d . . . C28 C 0.5671(3) 0.78988(15) 0.40756(11) 0.0207(4) Uani 1 1 d . . . C29 C 0.5224(3) 0.88283(16) 0.37576(12) 0.0228(5) Uani 1 1 d . . . C30 C 0.4396(3) 0.95721(17) 0.41780(13) 0.0292(5) Uani 1 1 d . . . H30 H 0.4057 0.9498 0.4684 0.035 Uiso 1 1 calc R . . C31 C 0.4074(3) 1.04296(18) 0.38423(15) 0.0349(6) Uani 1 1 d . . . H31 H 0.3506 1.0956 0.4114 0.042 Uiso 1 1 calc R . . C32 C 0.4595(3) 1.05040(17) 0.31041(15) 0.0339(6) Uani 1 1 d . . . H32 H 0.4399 1.1087 0.2862 0.041 Uiso 1 1 calc R . . C33 C 0.5404(3) 0.97218(17) 0.27223(13) 0.0292(5) Uani 1 1 d . . . H33 H 0.5752 0.9779 0.2215 0.035 Uiso 1 1 calc R . . C34 C 0.5469(3) 0.67188(17) 0.57930(12) 0.0255(5) Uani 1 1 d . . . C35 C 0.6339(3) 0.59829(19) 0.60639(13) 0.0338(6) Uani 1 1 d . . . H35 H 0.7128 0.5604 0.5745 0.041 Uiso 1 1 calc R . . C36 C 0.6059(4) 0.5802(2) 0.68000(14) 0.0392(6) Uani 1 1 d . . . H36 H 0.6661 0.5307 0.6989 0.047 Uiso 1 1 calc R . . C37 C 0.4889(3) 0.6352(2) 0.72523(13) 0.0350(6) Uani 1 1 d . . . C38 C 0.4001(3) 0.7087(2) 0.69968(13) 0.0348(6) Uani 1 1 d . . . H38 H 0.3200 0.7455 0.7318 0.042 Uiso 1 1 calc R . . C39 C 0.4306(3) 0.72740(18) 0.62614(12) 0.0288(5) Uani 1 1 d . . . H39 H 0.3721 0.7781 0.6077 0.035 Uiso 1 1 calc R . . Br2 Br 0.44567(4) 0.60694(3) 0.825611(14) 0.05158(11) Uani 1 1 d . . . P1 P 0.09457(8) 0.70521(5) 0.46436(3) 0.02756(14) Uani 1 1 d . . . F11 F -0.0710(2) 0.76764(13) 0.47429(11) 0.0521(4) Uani 1 1 d . . . F12 F 0.18276(18) 0.78955(11) 0.41455(8) 0.0382(4) Uani 1 1 d . . . F13 F 0.05271(19) 0.65663(12) 0.39397(8) 0.0411(4) Uani 1 1 d . . . F14 F 0.0072(2) 0.62138(16) 0.51237(10) 0.0626(6) Uani 1 1 d . . . F15 F 0.1374(2) 0.75581(18) 0.53273(9) 0.0654(6) Uani 1 1 d . . . F16 F 0.2611(2) 0.64399(12) 0.45139(10) 0.0485(4) Uani 1 1 d . . . P2 P 1.0000 0.5000 0.0000 0.0401(2) Uani 1 2 d S . . F21 F 0.9873(3) 0.59828(14) 0.04601(9) 0.0636(6) Uani 1 1 d . . . F22 F 1.0557(3) 0.44289(14) 0.06448(8) 0.0583(5) Uani 1 1 d . . . F23 F 0.8183(3) 0.48204(19) 0.03437(12) 0.0771(6) Uani 1 1 d . . . P3 P 0.5701(2) 0.02443(11) 0.05545(9) 0.0476(4) Uani 0.50 1 d P A -1 F31 F 0.5050(6) 0.0792(3) 0.1309(2) 0.0669(12) Uani 0.50 1 d P A -1 F32 F 0.5242(5) -0.0779(2) 0.09408(19) 0.0550(9) Uani 0.50 1 d P A -1 F33 F 0.7367(8) 0.0095(5) 0.0795(5) 0.096(3) Uani 0.50 1 d P A -1 F34 F 0.6135(11) 0.1248(5) 0.0185(5) 0.089(3) Uani 0.50 1 d P A -1 F35 F 0.3817(3) 0.03259(17) 0.02782(15) 0.0940(9) Uani 1 1 d . A -1 C41 C 1.005(2) 0.9948(13) 0.5131(4) 0.043(3) Uani 0.50 1 d P B -1 H41A H 1.0643 1.0541 0.5016 0.064 Uiso 0.50 1 calc PR B -1 H41B H 1.0804 0.9388 0.5095 0.064 Uiso 0.50 1 calc PR B -1 H41C H 0.9413 0.9995 0.5624 0.064 Uiso 0.50 1 calc PR B -1 C42 C 0.8976(8) 0.9826(4) 0.4622(3) 0.0372(12) Uani 0.50 1 d P B -1 N43 N 0.8104(7) 0.9741(4) 0.4238(3) 0.0510(13) Uani 0.50 1 d P B -1 C51 C 0.643(3) 0.1587(16) 0.0373(12) 0.046(5) Uani 0.25 1 d P C -2 H51A H 0.5908 0.1413 -0.0023 0.069 Uiso 0.25 1 calc PR C -2 H51B H 0.7457 0.1881 0.0176 0.069 Uiso 0.25 1 calc PR C -2 H51C H 0.5741 0.2050 0.0696 0.069 Uiso 0.25 1 calc PR C -2 C52 C 0.6717(15) 0.0730(10) 0.0768(6) 0.040(3) Uani 0.25 1 d P C -2 N53 N 0.688(3) 0.008(2) 0.1019(9) 0.074(4) Uani 0.25 1 d P C -2 C61 C 0.6568(16) 0.2139(12) 0.0302(6) 0.040(3) Uani 0.25 1 d P D -3 H61A H 0.6646 0.2833 0.0392 0.059 Uiso 0.25 1 calc PR D -3 H61B H 0.5706 0.2042 0.0038 0.059 Uiso 0.25 1 calc PR D -3 H61C H 0.7587 0.1884 0.0016 0.059 Uiso 0.25 1 calc PR D -3 C62 C 0.6228(15) 0.1640(9) 0.0975(7) 0.042(3) Uani 0.25 1 d P D -3 N63 N 0.596(2) 0.1221(11) 0.1494(7) 0.074(4) Uani 0.25 1 d P D -3 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu 0.02242(19) 0.02496(17) 0.01691(17) 0.00081(12) -0.00457(13) -0.00307(13) N1 0.0219(10) 0.0218(9) 0.0207(9) 0.0015(7) -0.0037(7) 0.0006(7) N2 0.0213(10) 0.0255(9) 0.0205(9) 0.0022(7) -0.0056(8) -0.0025(7) N3 0.0238(11) 0.0241(9) 0.0191(9) -0.0018(7) -0.0060(8) -0.0006(7) N4 0.0263(11) 0.0331(10) 0.0198(9) 0.0037(8) -0.0045(8) -0.0032(8) N5 0.0266(11) 0.0365(11) 0.0192(9) 0.0017(8) -0.0049(8) -0.0023(8) N6 0.0226(10) 0.0234(9) 0.0197(9) 0.0005(7) -0.0040(7) -0.0038(7) N7 0.0211(10) 0.0220(9) 0.0186(9) 0.0002(7) -0.0048(7) -0.0028(7) N8 0.0243(11) 0.0265(9) 0.0212(9) 0.0020(7) -0.0064(8) -0.0038(8) N9 0.0257(11) 0.0252(9) 0.0193(9) 0.0005(7) -0.0047(8) -0.0026(8) N10 0.0243(11) 0.0253(9) 0.0199(9) 0.0000(7) -0.0050(8) -0.0021(7) C1 0.0300(13) 0.0257(11) 0.0219(11) -0.0001(9) -0.0085(10) 0.0019(9) C2 0.0362(15) 0.0300(12) 0.0337(13) -0.0012(10) -0.0177(11) -0.0027(10) C3 0.0328(15) 0.0408(14) 0.0395(15) 0.0069(11) -0.0121(12) -0.0143(11) C4 0.0336(15) 0.0390(14) 0.0267(12) 0.0089(10) -0.0067(11) -0.0108(11) C5 0.0248(13) 0.0242(11) 0.0216(11) 0.0022(8) -0.0062(9) -0.0015(9) C6 0.0240(13) 0.0244(11) 0.0202(11) 0.0032(8) -0.0041(9) -0.0009(9) C7 0.0297(14) 0.0309(12) 0.0224(12) 0.0028(9) -0.0067(10) 0.0008(10) C8 0.0245(13) 0.0291(11) 0.0211(11) 0.0008(9) -0.0065(9) -0.0015(9) C9 0.0240(13) 0.0322(12) 0.0198(11) 0.0002(9) -0.0049(9) -0.0021(9) C10 0.0337(15) 0.0532(16) 0.0212(12) -0.0044(11) -0.0069(10) -0.0091(12) C11 0.0296(15) 0.0503(16) 0.0339(14) -0.0053(12) -0.0099(11) -0.0107(12) C12 0.0247(14) 0.0353(13) 0.0296(13) -0.0012(10) -0.0004(10) -0.0044(10) C13 0.0265(13) 0.0272(11) 0.0211(11) -0.0012(9) -0.0021(9) -0.0010(9) C14 0.0322(14) 0.0341(13) 0.0206(12) 0.0031(9) -0.0043(10) 0.0014(10) C15 0.062(2) 0.068(2) 0.0234(13) 0.0074(13) -0.0097(13) -0.0285(16) C16 0.065(2) 0.0582(18) 0.0248(14) 0.0076(12) -0.0027(13) -0.0251(16) C17 0.0489(17) 0.0291(12) 0.0164(11) 0.0018(9) -0.0022(10) 0.0106(11) C18 0.0378(15) 0.0457(15) 0.0203(12) -0.0009(10) -0.0095(11) 0.0071(12) C19 0.0300(14) 0.0463(15) 0.0216(12) 0.0012(10) -0.0037(10) 0.0005(11) Br1 0.0635(2) 0.03587(15) 0.01711(13) 0.00345(10) -0.00184(12) 0.01315(13) C21 0.0247(13) 0.0284(12) 0.0224(11) -0.0028(9) -0.0017(9) -0.0050(9) C22 0.0315(14) 0.0268(12) 0.0302(13) -0.0058(10) -0.0009(10) -0.0025(10) C23 0.0351(15) 0.0219(11) 0.0365(14) -0.0010(10) -0.0076(11) 0.0008(10) C24 0.0321(14) 0.0241(11) 0.0252(12) 0.0011(9) -0.0072(10) -0.0015(9) C25 0.0213(12) 0.0223(10) 0.0202(10) -0.0002(8) -0.0042(9) -0.0046(8) C26 0.0208(12) 0.0226(11) 0.0207(11) 0.0011(8) -0.0054(9) -0.0035(8) C27 0.0210(12) 0.0270(11) 0.0203(11) 0.0005(9) -0.0050(9) -0.0060(9) C28 0.0212(12) 0.0232(11) 0.0188(10) -0.0002(8) -0.0059(9) -0.0032(8) C29 0.0243(13) 0.0235(11) 0.0220(11) 0.0006(9) -0.0076(9) -0.0033(9) C30 0.0346(15) 0.0275(12) 0.0261(12) -0.0037(9) -0.0079(10) 0.0010(10) C31 0.0407(16) 0.0246(12) 0.0421(15) -0.0057(10) -0.0156(12) 0.0033(10) C32 0.0387(16) 0.0236(12) 0.0431(15) 0.0066(10) -0.0166(12) -0.0048(10) C33 0.0308(14) 0.0306(12) 0.0288(12) 0.0076(10) -0.0111(10) -0.0085(10) C34 0.0292(14) 0.0288(12) 0.0198(11) 0.0017(9) -0.0067(9) -0.0084(9) C35 0.0403(16) 0.0369(13) 0.0247(12) 0.0036(10) -0.0070(11) -0.0031(11) C36 0.0488(18) 0.0441(15) 0.0277(13) 0.0113(11) -0.0135(12) -0.0098(13) C37 0.0448(17) 0.0453(15) 0.0183(11) 0.0069(10) -0.0103(11) -0.0243(12) C38 0.0367(16) 0.0437(15) 0.0230(12) -0.0042(11) -0.0009(11) -0.0141(11) C39 0.0292(14) 0.0346(13) 0.0221(12) -0.0005(9) -0.0027(10) -0.0075(10) Br2 0.0657(2) 0.0746(2) 0.01823(14) 0.01159(13) -0.01154(13) -0.03515(17) P1 0.0270(3) 0.0365(3) 0.0198(3) 0.0017(2) -0.0056(2) -0.0053(2) F11 0.0298(9) 0.0525(10) 0.0725(12) -0.0148(9) -0.0067(8) 0.0004(7) F12 0.0373(9) 0.0375(8) 0.0423(9) 0.0083(7) -0.0114(7) -0.0132(6) F13 0.0437(10) 0.0482(9) 0.0339(8) -0.0075(7) -0.0109(7) -0.0148(7) F14 0.0507(11) 0.0874(14) 0.0549(11) 0.0441(10) -0.0188(9) -0.0286(10) F15 0.0499(12) 0.1202(18) 0.0264(8) -0.0247(10) -0.0045(8) -0.0213(11) F16 0.0342(9) 0.0420(9) 0.0725(12) 0.0056(8) -0.0183(8) -0.0002(7) P2 0.0517(7) 0.0490(6) 0.0166(4) -0.0019(4) -0.0041(4) 0.0224(5) F21 0.1027(16) 0.0559(11) 0.0341(9) -0.0074(8) -0.0244(10) 0.0302(11) F22 0.0893(14) 0.0605(11) 0.0239(8) -0.0013(7) -0.0152(8) 0.0350(10) F23 0.0565(14) 0.0995(17) 0.0667(14) 0.0153(12) 0.0052(10) 0.0127(12) P3 0.0413(9) 0.0412(8) 0.0494(9) 0.0158(7) 0.0136(7) 0.0155(7) F31 0.099(4) 0.044(2) 0.048(2) 0.0090(17) 0.003(2) 0.031(2) F32 0.067(3) 0.0402(18) 0.049(2) 0.0137(15) 0.0070(17) 0.0122(16) F33 0.068(4) 0.045(3) 0.185(9) -0.033(4) -0.056(5) 0.023(3) F34 0.095(5) 0.052(4) 0.091(5) 0.031(3) 0.049(4) 0.015(3) F35 0.0871(18) 0.0665(14) 0.1026(19) 0.0162(13) 0.0375(14) 0.0253(12) C41 0.055(4) 0.041(5) 0.027(7) -0.005(6) 0.003(7) 0.001(3) C42 0.037(3) 0.036(3) 0.035(3) -0.005(2) 0.003(3) -0.004(2) N43 0.050(3) 0.054(3) 0.046(3) -0.009(2) -0.002(3) -0.004(2) C51 0.046(9) 0.043(13) 0.051(13) 0.032(11) -0.016(7) 0.004(9) C52 0.041(7) 0.049(7) 0.032(6) 0.001(6) -0.012(5) -0.025(6) N53 0.114(11) 0.077(7) 0.034(5) 0.027(5) -0.027(6) 0.003(7) C61 0.042(7) 0.054(8) 0.020(6) 0.010(6) -0.003(5) 0.016(7) C62 0.043(7) 0.047(7) 0.034(7) 0.010(5) -0.006(5) 0.012(5) N63 0.114(11) 0.077(7) 0.034(5) 0.027(5) -0.027(6) 0.003(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag Cu N2 . . 1.9422(19) Y Cu N7 . . 2.0003(18) Y Cu N3 . . 2.1485(19) Y Cu N1 . . 2.1527(19) Y Cu N6 . . 2.2817(18) Y Cu N8 . . 2.321(2) Y N1 C1 . . 1.339(3) Y N1 C5 . . 1.355(3) Y N2 C6 . . 1.342(3) Y N2 C8 . . 1.342(3) Y N3 C13 . . 1.335(3) Y N3 C9 . . 1.354(3) Y N4 C6 . . 1.319(3) Y N4 C7 . . 1.352(3) Y N5 C8 . . 1.321(3) Y N5 C7 . . 1.348(3) Y N6 C21 . . 1.337(3) Y N6 C25 . . 1.348(3) Y N7 C26 . . 1.344(3) Y N7 C28 . . 1.345(3) Y N8 C33 . . 1.340(3) Y N8 C29 . . 1.344(3) Y N9 C26 . . 1.320(3) Y N9 C27 . . 1.342(3) Y N10 C28 . . 1.322(3) Y N10 C27 . . 1.354(3) Y C1 C2 . . 1.386(4) Y C1 H1 . . 0.95 ? C2 C3 . . 1.377(4) Y C2 H2 . . 0.95 ? C3 C4 . . 1.391(4) Y C3 H3 . . 0.95 ? C4 C5 . . 1.374(3) Y C4 H4 . . 0.95 ? C5 C6 . . 1.477(3) Y C7 C14 . . 1.465(3) Y C8 C9 . . 1.476(3) Y C9 C10 . . 1.379(3) Y C10 C11 . . 1.385(4) Y C10 H10 . . 0.95 ? C11 C12 . . 1.380(4) Y C11 H11 . . 0.95 ? C12 C13 . . 1.388(3) Y C12 H12 . . 0.95 ? C13 H13 . . 0.95 ? C14 C15 . . 1.387(4) Y C14 C19 . . 1.387(4) Y C15 C16 . . 1.378(4) Y C15 H15 . . 0.95 ? C16 C17 . . 1.375(4) Y C16 H16 . . 0.95 ? C17 C18 . . 1.373(4) Y C17 Br1 . . 1.901(2) Y C18 C19 . . 1.387(3) Y C18 H18 . . 0.95 ? C19 H19 . . 0.95 ? C21 C22 . . 1.389(3) Y C21 H21 . . 0.95 ? C22 C23 . . 1.382(4) Y C22 H22 . . 0.95 ? C23 C24 . . 1.390(3) Y C23 H23 . . 0.95 ? C24 C25 . . 1.381(3) Y C24 H24 . . 0.95 ? C25 C26 . . 1.480(3) Y C27 C34 . . 1.467(3) Y C28 C29 . . 1.484(3) Y C29 C30 . . 1.381(3) Y C30 C31 . . 1.386(3) Y C30 H30 . . 0.95 ? C31 C32 . . 1.383(4) Y C31 H31 . . 0.95 ? C32 C33 . . 1.382(4) Y C32 H32 . . 0.95 ? C33 H33 . . 0.95 ? C34 C35 . . 1.392(4) Y C34 C39 . . 1.396(3) Y C35 C36 . . 1.389(4) Y C35 H35 . . 0.95 ? C36 C37 . . 1.381(4) Y C36 H36 . . 0.95 ? C37 C38 . . 1.386(4) Y C37 Br2 . . 1.903(2) Y C38 C39 . . 1.389(3) Y C38 H38 . . 0.95 ? C39 H39 . . 0.95 ? P1 F15 . . 1.5821(17) Y P1 F14 . . 1.5835(17) Y P1 F16 . . 1.5991(17) Y P1 F13 . . 1.5997(15) Y P1 F11 . . 1.6034(18) Y P1 F12 . . 1.6081(15) Y P2 F23 . . 1.583(2) Y P2 F23 . 2_765 1.583(2) Y P2 F22 . . 1.5916(15) Y P2 F22 . 2_765 1.5916(15) Y P2 F21 . . 1.6009(18) Y P2 F21 . 2_765 1.6010(18) Y P3 F34 . . 1.573(7) Y P3 F33 . . 1.580(7) Y P3 F31 . . 1.604(4) Y P3 F32 . . 1.614(4) Y P3 F35 . . 1.784(4) Y C41 C42 . . 1.468(15) Y C41 H41a . . 0.98 ? C41 H41b . . 0.98 ? C41 H41c . . 0.98 ? C42 N43 . . 1.146(8) Y C51 C52 . . 1.44(2) Y C51 H51a . . 0.98 ? C51 H51b . . 0.98 ? C51 H51c . . 0.98 ? C52 N53 . . 1.03(3) Y C61 C62 . . 1.428(16) Y C61 H61a . . 0.98 ? C61 H61b . . 0.98 ? C61 H61c . . 0.98 ? C62 N63 . . 1.127(17) Y loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_2 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag N2 CU N7 . . . 177.54(8) Y N2 CU N3 . . . 77.10(7) Y N7 CU N3 . . . 102.91(7) Y N2 CU N1 . . . 77.23(7) Y N7 CU N1 . . . 102.94(7) Y N3 CU N1 . . . 153.89(7) Y N2 CU N6 . . . 101.77(7) Y N7 CU N6 . . . 75.77(7) Y N3 CU N6 . . . 92.03(7) Y N1 CU N6 . . . 97.75(7) Y N2 CU N8 . . . 108.11(7) Y N7 CU N8 . . . 74.35(7) Y N3 CU N8 . . . 94.89(7) Y N1 CU N8 . . . 88.60(7) Y N6 CU N8 . . . 150.12(7) Y C1 N1 C5 . . . 117.8(2) Y C1 N1 CU . . . 128.41(16) Y C5 N1 CU . . . 113.68(14) Y C6 N2 C8 . . . 116.77(19) Y C6 N2 CU . . . 121.63(15) Y C8 N2 CU . . . 121.60(16) Y C13 N3 C9 . . . 117.99(19) Y C13 N3 CU . . . 128.23(15) Y C9 N3 CU . . . 113.67(15) Y C6 N4 C7 . . . 115.4(2) Y C8 N5 C7 . . . 115.3(2) Y C21 N6 C25 . . . 117.37(19) Y C21 N6 CU . . . 130.24(15) Y C25 N6 CU . . . 111.95(14) Y C26 N7 C28 . . . 115.98(18) Y C26 N7 CU . . . 120.96(15) Y C28 N7 CU . . . 123.05(14) Y C33 N8 C29 . . . 117.5(2) Y C33 N8 CU . . . 130.12(16) Y C29 N8 CU . . . 112.37(14) Y C26 N9 C27 . . . 115.86(19) Y C28 N10 C27 . . . 115.18(19) Y N1 C1 C2 . . . 122.1(2) Y N1 C1 H1 . . . 118.9 ? C2 C1 H1 . . . 118.9 ? C3 C2 C1 . . . 119.5(2) Y C3 C2 H2 . . . 120.2 ? C1 C2 H2 . . . 120.2 ? C2 C3 C4 . . . 119.0(2) Y C2 C3 H3 . . . 120.5 ? C4 C3 H3 . . . 120.5 ? C5 C4 C3 . . . 118.2(2) Y C5 C4 H4 . . . 120.9 ? C3 C4 H4 . . . 120.9 ? N1 C5 C4 . . . 123.4(2) Y N1 C5 C6 . . . 113.7(2) Y C4 C5 C6 . . . 122.9(2) Y N4 C6 N2 . . . 123.9(2) Y N4 C6 C5 . . . 122.5(2) Y N2 C6 C5 . . . 113.66(19) Y N5 C7 N4 . . . 124.7(2) Y N5 C7 C14 . . . 118.0(2) Y N4 C7 C14 . . . 117.3(2) Y N5 C8 N2 . . . 124.0(2) Y N5 C8 C9 . . . 122.5(2) Y N2 C8 C9 . . . 113.48(19) Y N3 C9 C10 . . . 123.1(2) Y N3 C9 C8 . . . 113.61(19) Y C10 C9 C8 . . . 123.3(2) Y C9 C10 C11 . . . 118.3(2) Y C9 C10 H10 . . . 120.8 ? C11 C10 H10 . . . 120.8 ? C12 C11 C10 . . . 119.1(2) Y C12 C11 H11 . . . 120.5 ? C10 C11 H11 . . . 120.5 ? C11 C12 C13 . . . 119.4(2) Y C11 C12 H12 . . . 120.3 ? C13 C12 H12 . . . 120.3 ? N3 C13 C12 . . . 122.2(2) Y N3 C13 H13 . . . 118.9 ? C12 C13 H13 . . . 118.9 ? C15 C14 C19 . . . 118.8(2) Y C15 C14 C7 . . . 120.3(2) Y C19 C14 C7 . . . 120.9(2) Y C16 C15 C14 . . . 121.1(3) Y C16 C15 H15 . . . 119.4 ? C14 C15 H15 . . . 119.4 ? C17 C16 C15 . . . 118.8(3) Y C17 C16 H16 . . . 120.6 ? C15 C16 H16 . . . 120.6 ? C18 C17 C16 . . . 121.7(2) Y C18 C17 BR1 . . . 119.3(2) Y C16 C17 BR1 . . . 119.0(2) Y C17 C18 C19 . . . 119.0(2) Y C17 C18 H18 . . . 120.5 ? C19 C18 H18 . . . 120.5 ? C14 C19 C18 . . . 120.6(3) Y C14 C19 H19 . . . 119.7 ? C18 C19 H19 . . . 119.7 ? N6 C21 C22 . . . 122.6(2) Y N6 C21 H21 . . . 118.7 ? C22 C21 H21 . . . 118.7 ? C23 C22 C21 . . . 119.1(2) Y C23 C22 H22 . . . 120.4 ? C21 C22 H22 . . . 120.4 ? C22 C23 C24 . . . 119.1(2) Y C22 C23 H23 . . . 120.4 ? C24 C23 H23 . . . 120.4 ? C25 C24 C23 . . . 117.7(2) Y C25 C24 H24 . . . 121.1 ? C23 C24 H24 . . . 121.1 ? N6 C25 C24 . . . 124.0(2) Y N6 C25 C26 . . . 114.60(19) Y C24 C25 C26 . . . 121.4(2) Y N9 C26 N7 . . . 124.1(2) Y N9 C26 C25 . . . 119.64(19) Y N7 C26 C25 . . . 116.27(19) Y N9 C27 N10 . . . 124.4(2) Y N9 C27 C34 . . . 117.2(2) Y N10 C27 C34 . . . 118.4(2) Y N10 C28 N7 . . . 124.4(2) Y N10 C28 C29 . . . 120.0(2) Y N7 C28 C29 . . . 115.50(19) Y N8 C29 C30 . . . 123.5(2) Y N8 C29 C28 . . . 114.6(2) Y C30 C29 C28 . . . 121.9(2) Y C29 C30 C31 . . . 118.3(2) Y C29 C30 H30 . . . 120.9 ? C31 C30 H30 . . . 120.9 ? C32 C31 C30 . . . 118.8(2) Y C32 C31 H31 . . . 120.6 ? C30 C31 H31 . . . 120.6 ? C33 C32 C31 . . . 119.3(2) Y C33 C32 H32 . . . 120.4 ? C31 C32 H32 . . . 120.4 ? N8 C33 C32 . . . 122.7(2) Y N8 C33 H33 . . . 118.7 ? C32 C33 H33 . . . 118.7 ? C35 C34 C39 . . . 120.0(2) Y C35 C34 C27 . . . 119.3(2) Y C39 C34 C27 . . . 120.8(2) Y C36 C35 C34 . . . 120.2(3) Y C36 C35 H35 . . . 119.9 ? C34 C35 H35 . . . 119.9 ? C37 C36 C35 . . . 118.9(3) Y C37 C36 H36 . . . 120.6 ? C35 C36 H36 . . . 120.6 ? C36 C37 C38 . . . 122.2(2) Y C36 C37 BR2 . . . 118.7(2) Y C38 C37 BR2 . . . 119.1(2) Y C37 C38 C39 . . . 118.6(3) Y C37 C38 H38 . . . 120.7 ? C39 C38 H38 . . . 120.7 ? C38 C39 C34 . . . 120.2(2) Y C38 C39 H39 . . . 119.9 ? C34 C39 H39 . . . 119.9 ? F15 P1 F14 . . . 91.53(12) Y F15 P1 F16 . . . 90.41(11) Y F14 P1 F16 . . . 91.05(10) Y F15 P1 F13 . . . 178.44(11) Y F14 P1 F13 . . . 90.0(1) Y F16 P1 F13 . . . 89.88(10) Y F15 P1 F11 . . . 90.98(11) Y F14 P1 F11 . . . 90.49(11) Y F16 P1 F11 . . . 177.90(11) Y F13 P1 F11 . . . 88.69(9) Y F15 P1 F12 . . . 89.32(10) Y F14 P1 F12 . . . 179.15(10) Y F16 P1 F12 . . . 88.91(9) Y F13 P1 F12 . . . 89.15(8) Y F11 P1 F12 . . . 89.53(9) Y F23 P2 F23 . . 2_765 179.998(1) Y F23 P2 F22 . . . 90.49(11) Y F23 P2 F22 2_765 . . 89.51(11) Y F23 P2 F22 . . 2_765 89.51(11) Y F23 P2 F22 2_765 . 2_765 90.49(11) Y F22 P2 F22 . . 2_765 179.998(2) Y F23 P2 F21 . . . 89.14(13) Y F23 P2 F21 2_765 . . 90.86(13) Y F22 P2 F21 . . . 89.41(9) Y F22 P2 F21 2_765 . . 90.59(9) Y F23 P2 F21 . . 2_765 90.86(13) Y F23 P2 F21 2_765 . 2_765 89.14(13) Y F22 P2 F21 . . 2_765 90.59(9) Y F22 P2 F21 2_765 . 2_765 89.41(9) Y F21 P2 F21 . . 2_765 180 Y F34 P3 F33 . . . 93.9(5) Y F34 P3 F31 . . . 89.8(3) Y F33 P3 F31 . . . 87.6(4) Y F34 P3 F32 . . . 179.4(4) Y F33 P3 F32 . . . 86.3(3) Y F31 P3 F32 . . . 89.6(2) Y F34 P3 F35 . . . 89.4(4) Y F33 P3 F35 . . . 176.1(3) Y F31 P3 F35 . . . 94.4(2) Y F32 P3 F35 . . . 90.43(19) Y N43 C42 C41 . . . 178.1(8) Y C52 C51 H51A . . . 109.5 ? C52 C51 H51B . . . 109.5 ? H51A C51 H51B . . . 109.5 ? C52 C51 H51C . . . 109.5 ? H51A C51 H51C . . . 109.5 ? H51B C51 H51C . . . 109.5 ? N53 C52 C51 . . . 175.00(19) Y N63 C62 C61 . . . 177.90(16) Y loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion _geom_torsion_publ_flag N2 CU N1 C1 . . . . 178.1(2) N N7 CU N1 C1 . . . . -4.4(2) N N3 CU N1 C1 . . . . 167.46(17) N N6 CU N1 C1 . . . . -81.50(19) N N8 CU N1 C1 . . . . 69.19(19) N N2 CU N1 C5 . . . . 2.72(15) N N7 CU N1 C5 . . . . -179.80(15) N N3 CU N1 C5 . . . . -7.9(3) N N6 CU N1 C5 . . . . 103.11(15) N N8 CU N1 C5 . . . . -106.20(15) N N3 CU N2 C6 . . . . 173.92(18) N N1 CU N2 C6 . . . . -1.30(17) N N6 CU N2 C6 . . . . -96.69(17) N N8 CU N2 C6 . . . . 82.94(18) N N3 CU N2 C8 . . . . -5.45(17) N N1 CU N2 C8 . . . . 179.33(19) N N6 CU N2 C8 . . . . 83.94(18) N N8 CU N2 C8 . . . . -96.43(18) N N2 CU N3 C13 . . . . -177.1(2) N N7 CU N3 C13 . . . . 5.5(2) N N1 CU N3 C13 . . . . -166.41(17) N N6 CU N3 C13 . . . . 81.32(19) N N8 CU N3 C13 . . . . -69.59(19) N N2 CU N3 C9 . . . . 6.78(15) N N7 CU N3 C9 . . . . -170.69(15) N N1 CU N3 C9 . . . . 17.4(3) N N6 CU N3 C9 . . . . -94.83(16) N N8 CU N3 C9 . . . . 114.27(16) N N2 CU N6 C21 . . . . 2.3(2) N N7 CU N6 C21 . . . . -177.6(2) N N3 CU N6 C21 . . . . 79.6(2) N N1 CU N6 C21 . . . . -76.2(2) N N8 CU N6 C21 . . . . -176.96(17) N N2 CU N6 C25 . . . . 174.34(15) N N7 CU N6 C25 . . . . -5.61(15) N N3 CU N6 C25 . . . . -108.42(15) N N1 CU N6 C25 . . . . 95.85(15) N N8 CU N6 C25 . . . . -4.9(2) N N3 CU N7 C26 . . . . 91.55(17) N N1 CU N7 C26 . . . . -92.11(17) N N6 CU N7 C26 . . . . 2.73(16) N N8 CU N7 C26 . . . . -176.93(18) N N3 CU N7 C28 . . . . -90.03(17) N N1 CU N7 C28 . . . . 86.31(18) N N6 CU N7 C28 . . . . -178.85(18) N N8 CU N7 C28 . . . . 1.49(16) N N2 CU N8 C33 . . . . -1.1(2) N N7 CU N8 C33 . . . . 178.8(2) N N3 CU N8 C33 . . . . -79.1(2) N N1 CU N8 C33 . . . . 75.0(2) N N6 CU N8 C33 . . . . 178.14(18) N N2 CU N8 C29 . . . . 176.93(15) N N7 CU N8 C29 . . . . -3.14(15) N N3 CU N8 C29 . . . . 98.93(16) N N1 CU N8 C29 . . . . -106.99(16) N N6 CU N8 C29 . . . . -3.8(2) N C5 N1 C1 C2 . . . . 0.2(3) N CU N1 C1 C2 . . . . -175.00(17) N N1 C1 C2 C3 . . . . 0.4(4) N C1 C2 C3 C4 . . . . -0.6(4) N C2 C3 C4 C5 . . . . 0.3(4) N C1 N1 C5 C4 . . . . -0.6(3) N CU N1 C5 C4 . . . . 175.33(19) N C1 N1 C5 C6 . . . . -179.51(19) N CU N1 C5 C6 . . . . -3.6(2) N C3 C4 C5 N1 . . . . 0.3(4) N C3 C4 C5 C6 . . . . 179.2(2) N C7 N4 C6 N2 . . . . -0.6(3) N C7 N4 C6 C5 . . . . 179.9(2) N C8 N2 C6 N4 . . . . -0.4(3) N CU N2 C6 N4 . . . . -179.78(17) N C8 N2 C6 C5 . . . . 179.16(19) N CU N2 C6 C5 . . . . -0.2(3) N N1 C5 C6 N4 . . . . -177.8(2) N C4 C5 C6 N4 . . . . 3.3(4) N N1 C5 C6 N2 . . . . 2.6(3) N C4 C5 C6 N2 . . . . -176.3(2) N C8 N5 C7 N4 . . . . 0.4(3) N C8 N5 C7 C14 . . . . -177.7(2) N C6 N4 C7 N5 . . . . 0.6(3) N C6 N4 C7 C14 . . . . 178.7(2) N C7 N5 C8 N2 . . . . -1.5(3) N C7 N5 C8 C9 . . . . 175.9(2) N C6 N2 C8 N5 . . . . 1.5(3) N CU N2 C8 N5 . . . . -179.06(18) N C6 N2 C8 C9 . . . . -176.12(19) N CU N2 C8 C9 . . . . 3.3(3) N C13 N3 C9 C10 . . . . -1.3(3) N CU N3 C9 C10 . . . . 175.3(2) N C13 N3 C9 C8 . . . . 176.4(2) N CU N3 C9 C8 . . . . -7.1(2) N N5 C8 C9 N3 . . . . -174.7(2) N N2 C8 C9 N3 . . . . 3.0(3) N N5 C8 C9 C10 . . . . 2.9(4) N N2 C8 C9 C10 . . . . -179.4(2) N N3 C9 C10 C11 . . . . 0.7(4) N C8 C9 C10 C11 . . . . -176.7(2) N C9 C10 C11 C12 . . . . 0.7(4) N C10 C11 C12 C13 . . . . -1.3(4) N C9 N3 C13 C12 . . . . 0.5(3) N CU N3 C13 C12 . . . . -175.47(17) N C11 C12 C13 N3 . . . . 0.8(4) N N5 C7 C14 C15 . . . . 171.3(3) N N4 C7 C14 C15 . . . . -6.9(4) N N5 C7 C14 C19 . . . . -6.5(4) N N4 C7 C14 C19 . . . . 175.2(2) N C19 C14 C15 C16 . . . . -0.3(5) N C7 C14 C15 C16 . . . . -178.2(3) N C14 C15 C16 C17 . . . . 0.4(5) N C15 C16 C17 C18 . . . . -0.4(5) N C15 C16 C17 BR1 . . . . -179.4(3) N C16 C17 C18 C19 . . . . 0.2(4) N BR1 C17 C18 C19 . . . . 179.24(19) N C15 C14 C19 C18 . . . . 0.0(4) N C7 C14 C19 C18 . . . . 177.9(2) N C17 C18 C19 C14 . . . . 0.0(4) N C25 N6 C21 C22 . . . . -2.4(3) N CU N6 C21 C22 . . . . 169.22(17) N N6 C21 C22 C23 . . . . 0.5(4) N C21 C22 C23 C24 . . . . 1.7(4) N C22 C23 C24 C25 . . . . -1.9(4) N C21 N6 C25 C24 . . . . 2.2(3) N CU N6 C25 C24 . . . . -170.90(18) N C21 N6 C25 C26 . . . . -179.48(19) N CU N6 C25 C26 . . . . 7.4(2) N C23 C24 C25 N6 . . . . -0.1(4) N C23 C24 C25 C26 . . . . -178.3(2) N C27 N9 C26 N7 . . . . -2.1(3) N C27 N9 C26 C25 . . . . 178.01(19) N C28 N7 C26 N9 . . . . 1.9(3) N CU N7 C26 N9 . . . . -179.57(17) N C28 N7 C26 C25 . . . . -178.18(19) N CU N7 C26 C25 . . . . 0.3(3) N N6 C25 C26 N9 . . . . 174.32(19) N C24 C25 C26 N9 . . . . -7.4(3) N N6 C25 C26 N7 . . . . -5.6(3) N C24 C25 C26 N7 . . . . 172.7(2) N C26 N9 C27 N10 . . . . 0.5(3) N C26 N9 C27 C34 . . . . -178.7(2) N C28 N10 C27 N9 . . . . 1.1(3) N C28 N10 C27 C34 . . . . -179.7(2) N C27 N10 C28 N7 . . . . -1.3(3) N C27 N10 C28 C29 . . . . 179.9(2) N C26 N7 C28 N10 . . . . -0.1(3) N CU N7 C28 N10 . . . . -178.56(17) N C26 N7 C28 C29 . . . . 178.74(19) N CU N7 C28 C29 . . . . 0.2(3) N C33 N8 C29 C30 . . . . 1.2(3) N CU N8 C29 C30 . . . . -177.10(19) N C33 N8 C29 C28 . . . . -177.5(2) N CU N8 C29 C28 . . . . 4.2(2) N N10 C28 C29 N8 . . . . 175.7(2) N N7 C28 C29 N8 . . . . -3.2(3) N N10 C28 C29 C30 . . . . -3.1(3) N N7 C28 C29 C30 . . . . 178.0(2) N N8 C29 C30 C31 . . . . -0.9(4) N C28 C29 C30 C31 . . . . 177.8(2) N C29 C30 C31 C32 . . . . -0.1(4) N C30 C31 C32 C33 . . . . 0.7(4) N C29 N8 C33 C32 . . . . -0.6(3) N CU N8 C33 C32 . . . . 177.35(18) N C31 C32 C33 N8 . . . . -0.3(4) N N9 C27 C34 C35 . . . . 19.5(3) N N10 C27 C34 C35 . . . . -159.7(2) N N9 C27 C34 C39 . . . . -161.0(2) N N10 C27 C34 C39 . . . . 19.8(3) N C39 C34 C35 C36 . . . . -0.3(4) N C27 C34 C35 C36 . . . . 179.2(2) N C34 C35 C36 C37 . . . . 1.0(4) N C35 C36 C37 C38 . . . . -0.8(4) N C35 C36 C37 BR2 . . . . 177.8(2) N C36 C37 C38 C39 . . . . -0.2(4) N BR2 C37 C38 C39 . . . . -178.76(18) N C37 C38 C39 C34 . . . . 1.0(4) N C35 C34 C39 C38 . . . . -0.8(4) N C27 C34 C39 C38 . . . . 179.8(2) N _diffrn_measured_fraction_theta_max 0.961 _diffrn_reflns_theta_full 67.94 _diffrn_measured_fraction_theta_full 0.961 _refine_diff_density_max 1.495 _refine_diff_density_min -0.747 _refine_diff_density_rms 0.068 # Attachment '611628.cif' data_gar122 _database_code_depnum_ccdc_archive 'CCDC 611628' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C38 H24 Br2 Cu N10, 2(F6 P), 2(C3 H6 O)' _chemical_formula_sum 'C44 H36 Br2 Cu F12 N10 O2 P2' _chemical_formula_weight 1250.13 _chemical_compound_source 'Synthesized by the authors. See text' 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 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu -1.9646 0.5888 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.6763 1.2805 '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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M C2/c _symmetry_space_group_name_hall '-C 2yc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 14.8156(2) _cell_length_b 21.3172(4) _cell_length_c 16.7458(3) _cell_angle_alpha 90.00 _cell_angle_beta 95.3930(10) _cell_angle_gamma 90.00 _cell_volume 5265.37(15) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 14604 _cell_measurement_theta_min 3.64 _cell_measurement_theta_max 68.64 _exptl_crystal_description block _exptl_crystal_colour green _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.577 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2492 _exptl_absorpt_coefficient_mu 3.732 _exptl_absorpt_correction_Type multi-scan _exptl_absorpt_correction_T_min 0.7800 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details 'Sadabs (Sheldrick,1996)' _exptl_special_details ; X-ray crystallographic data for I were collected from a single crystal sample, which was mounted on a loop fiber. Data were collected using a Bruker Platform diffractometer, equipped with a Bruker SMART 4K Charged-Coupled Device (CCD) Area Detector using the program SMART and a rotating anode source Cu-K\a radiation. The crystal-to-detector distance was 5.120 cm, and the data collection was carried out in 512 x 512 pixel mode, utilizing 4 x 4 pixel binning. The initial unit cell parameters were determined by a least-squares fit of the angular setting of strong reflections, collected by a 9.0 degree scan in 30 frames over four different parts of the reciprocal space (120 frames total). Upon completion of the data collection, the first 101 frames were recollected in order to improve the decay correction analysis. ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'Rotating Anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker AXS Smart 4K/Platform' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 5.5 _diffrn_standards_number 222 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% -0.01 _diffrn_reflns_number 60135 _diffrn_reflns_av_R_equivalents 0.023 _diffrn_reflns_av_sigmaI/netI 0.0135 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -25 _diffrn_reflns_limit_k_max 25 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 3.64 _diffrn_reflns_theta_max 68.88 _reflns_number_total 4823 _reflns_number_gt 4252 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'SMART (Bruker, 2001)' _computing_cell_refinement 'SMART (Bruker, 2001)' _computing_data_reduction 'SAINT (Bruker, 2003)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL (Bruker, 1997)' _computing_publication_material 'UdMX (local program)' _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^)+(0.1135P)^2^+16.5641P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4823 _refine_ls_number_parameters 425 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0679 _refine_ls_R_factor_gt 0.0617 _refine_ls_wR_factor_ref 0.1889 _refine_ls_wR_factor_gt 0.1792 _refine_ls_goodness_of_fit_ref 1.046 _refine_ls_restrained_S_all 1.046 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu 0.0000 0.26811(3) 0.2500 0.0376(2) Uani 1 2 d S . . N1 N 0.0773(2) 0.34126(14) 0.31997(17) 0.0405(6) Uani 1 1 d . . . N2 N 0.1186(2) 0.26563(13) 0.20853(17) 0.0353(6) Uani 1 1 d . . . N3 N -0.0177(2) 0.19687(15) 0.15224(18) 0.0447(7) Uani 1 1 d . . . N4 N 0.27179(19) 0.29654(14) 0.21956(16) 0.0367(6) Uani 1 1 d . . . N5 N 0.2148(2) 0.22359(14) 0.11893(18) 0.0402(7) Uani 1 1 d . . . C1 C 0.0489(3) 0.3818(2) 0.3732(2) 0.0501(9) Uani 1 1 d . . . H1 H -0.0134 0.3820 0.3824 0.060 Uiso 1 1 calc R . . C2 C 0.1069(3) 0.4232(2) 0.4152(2) 0.0551(10) Uani 1 1 d . . . H2 H 0.0848 0.4511 0.4531 0.066 Uiso 1 1 calc R . . C3 C 0.1973(3) 0.42380(19) 0.4017(2) 0.0523(9) Uani 1 1 d . . . H3 H 0.2383 0.4516 0.4307 0.063 Uiso 1 1 calc R . . C4 C 0.2274(3) 0.38322(17) 0.3452(2) 0.0430(8) Uani 1 1 d . . . H4 H 0.2890 0.3831 0.3338 0.052 Uiso 1 1 calc R . . C5 C 0.1653(2) 0.34304(16) 0.30603(19) 0.0363(7) Uani 1 1 d . . . C6 C 0.1888(2) 0.29982(15) 0.24186(19) 0.0347(7) Uani 1 1 d . . . C7 C 0.2824(2) 0.25825(17) 0.1572(2) 0.0387(7) Uani 1 1 d . . . C8 C 0.1363(2) 0.22759(16) 0.1478(2) 0.0369(7) Uani 1 1 d . . . C9 C 0.0583(2) 0.18877(18) 0.1154(2) 0.0418(8) Uani 1 1 d . . . C10 C 0.0658(3) 0.1466(2) 0.0533(3) 0.0560(10) Uani 1 1 d . . . H10 H 0.1204 0.1429 0.0282 0.067 Uiso 1 1 calc R . . C11 C -0.0092(4) 0.1099(3) 0.0290(3) 0.0750(14) Uani 1 1 d . . . H11 H -0.0066 0.0799 -0.0127 0.090 Uiso 1 1 calc R . . C12 C -0.0882(4) 0.1177(3) 0.0665(4) 0.0797(16) Uani 1 1 d . . . H12 H -0.1403 0.0931 0.0507 0.096 Uiso 1 1 calc R . . C13 C -0.0901(3) 0.1622(2) 0.1277(3) 0.0626(11) Uani 1 1 d . . . H13 H -0.1446 0.1678 0.1526 0.075 Uiso 1 1 calc R . . C14 C 0.3724(3) 0.2518(2) 0.1296(2) 0.0439(8) Uani 1 1 d . . . C15 C 0.4428(3) 0.2918(2) 0.1566(3) 0.0551(10) Uani 1 1 d . . . H15 H 0.4318 0.3250 0.1923 0.066 Uiso 1 1 calc R . . C16 C 0.5282(3) 0.2840(3) 0.1324(3) 0.0675(13) Uani 1 1 d . . . H16 H 0.5760 0.3114 0.1514 0.081 Uiso 1 1 calc R . . C17 C 0.5435(3) 0.2363(2) 0.0807(3) 0.0608(12) Uani 1 1 d . . . C18 C 0.4750(3) 0.1959(3) 0.0526(3) 0.0717(14) Uani 1 1 d . . . H18 H 0.4868 0.1628 0.0170 0.086 Uiso 1 1 calc R . . C19 C 0.3895(3) 0.2040(2) 0.0767(3) 0.0577(11) Uani 1 1 d . . . H19 H 0.3418 0.1767 0.0571 0.069 Uiso 1 1 calc R . . Br1 Br 0.66067(3) 0.22643(4) 0.04540(4) 0.0862(3) Uani 1 1 d . . . P1 P 0.22217(9) 0.44218(5) 0.08111(6) 0.0595(3) Uani 1 1 d . . . F11 F 0.1490(9) 0.4462(5) 0.0160(7) 0.117(5) Uani 0.50 1 d P A -1 F12 F 0.2240(17) 0.5190(11) 0.0933(16) 0.070(3) Uani 0.50 1 d P A -1 F13 F 0.2978(8) 0.4617(4) 0.0114(5) 0.106(3) Uani 0.50 1 d P A -1 F14 F 0.2440(8) 0.3716(3) 0.0643(4) 0.100(3) Uani 0.50 1 d P A -1 F15 F 0.1679(9) 0.4342(8) 0.1502(8) 0.104(5) Uani 0.50 1 d P A -1 F16 F 0.3139(7) 0.4414(4) 0.1460(5) 0.085(3) Uani 0.50 1 d P A -1 F111 F 0.1151(6) 0.4612(4) 0.0492(6) 0.083(3) Uani 0.50 1 d P A -2 F112 F 0.2468(16) 0.5098(10) 0.0819(14) 0.089(5) Uani 0.50 1 d P A -2 F113 F 0.2366(7) 0.4341(3) -0.0089(4) 0.084(2) Uani 0.50 1 d P A -2 F114 F 0.1778(4) 0.3698(3) 0.0821(3) 0.0574(13) Uani 0.50 1 d P A -2 F115 F 0.1970(10) 0.4415(6) 0.1712(7) 0.093(4) Uani 0.50 1 d P A -2 F116 F 0.3148(6) 0.4170(5) 0.1081(6) 0.096(3) Uani 0.50 1 d P A -2 C21 C 0.3842(10) 0.0883(7) 0.271(2) 0.32(2) Uani 0.717(5) 1 d P B -1 H21A H 0.4248 0.1173 0.2469 0.487 Uiso 0.717(5) 1 calc PR B -1 H21B H 0.3927 0.0458 0.2509 0.487 Uiso 0.717(5) 1 calc PR B -1 H21C H 0.3980 0.0886 0.3297 0.487 Uiso 0.717(5) 1 calc PR B -1 C22 C 0.2987(6) 0.1060(3) 0.2530(4) 0.078(2) Uani 0.717(5) 1 d P B -1 C23 C 0.2324(19) 0.0602(6) 0.2079(8) 0.253(15) Uani 0.717(5) 1 d P B -1 H23A H 0.1708 0.0773 0.2055 0.379 Uiso 0.717(5) 1 calc PR B -1 H23B H 0.2345 0.0198 0.2360 0.379 Uiso 0.717(5) 1 calc PR B -1 H23C H 0.2496 0.0541 0.1533 0.379 Uiso 0.717(5) 1 calc PR B -1 O24 O 0.2630(4) 0.1502(2) 0.2694(3) 0.0759(15) Uani 0.717(5) 1 d P B -1 O34 O 0.0540(7) 0.9260(6) 0.1884(7) 0.061(3) Uani 0.283(5) 1 d P B -2 C32 C 0.0452(12) 0.9690(9) 0.2262(12) 0.047(5) Uani 0.283(5) 1 d P B -2 C31 C 0.092(2) 1.0263(12) 0.2202(16) 0.109(9) Uani 0.283(5) 1 d P B -2 H31A H 0.1239 1.0368 0.2724 0.164 Uiso 0.283(5) 1 calc PR B -2 H31B H 0.0483 1.0596 0.2040 0.164 Uiso 0.283(5) 1 calc PR B -2 H31C H 0.1356 1.0223 0.1801 0.164 Uiso 0.283(5) 1 calc PR B -2 C33 C -0.0104(14) 0.9629(10) 0.2920(14) 0.058(6) Uani 0.283(5) 1 d P B -2 H33A H -0.0735 0.9725 0.2732 0.087 Uiso 0.283(5) 1 calc PR B -2 H33B H 0.0110 0.9921 0.3348 0.087 Uiso 0.283(5) 1 calc PR B -2 H33C H -0.0064 0.9198 0.3125 0.087 Uiso 0.283(5) 1 calc PR B -2 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.0296(4) 0.0472(4) 0.0364(4) 0.000 0.0054(3) 0.000 N1 0.0346(15) 0.0525(16) 0.0354(14) -0.0009(12) 0.0078(11) 0.0003(12) N2 0.0306(14) 0.0430(15) 0.0328(14) -0.0008(11) 0.0053(11) -0.0019(11) N3 0.0329(15) 0.0581(18) 0.0434(16) -0.0037(14) 0.0061(12) -0.0037(13) N4 0.0323(14) 0.0447(15) 0.0340(14) -0.0021(12) 0.0070(11) -0.0025(11) N5 0.0322(15) 0.0516(17) 0.0375(15) -0.0068(12) 0.0065(12) -0.0056(12) C1 0.046(2) 0.064(2) 0.0425(19) -0.0011(17) 0.0139(16) 0.0104(18) C2 0.065(3) 0.056(2) 0.046(2) -0.0069(18) 0.0125(19) 0.011(2) C3 0.061(2) 0.051(2) 0.044(2) -0.0089(17) 0.0019(18) -0.0018(18) C4 0.0390(19) 0.0481(19) 0.0419(18) -0.0029(15) 0.0042(15) -0.0009(15) C5 0.0345(17) 0.0426(17) 0.0322(16) 0.0000(13) 0.0050(13) 0.0008(13) C6 0.0320(16) 0.0400(16) 0.0322(15) 0.0011(13) 0.0039(12) -0.0012(13) C7 0.0337(18) 0.0482(18) 0.0348(17) 0.0003(14) 0.0066(14) -0.0032(14) C8 0.0334(18) 0.0449(18) 0.0329(16) -0.0018(13) 0.0054(13) -0.0007(13) C9 0.0344(17) 0.0511(19) 0.0397(18) -0.0035(15) 0.0029(14) -0.0047(15) C10 0.052(2) 0.068(3) 0.049(2) -0.0180(19) 0.0099(18) -0.0101(19) C11 0.068(3) 0.088(3) 0.069(3) -0.030(3) 0.005(2) -0.022(3) C12 0.058(3) 0.098(4) 0.082(3) -0.018(3) 0.000(2) -0.035(3) C13 0.036(2) 0.085(3) 0.067(3) -0.003(2) 0.0067(18) -0.014(2) C14 0.0327(18) 0.060(2) 0.0401(19) -0.0046(16) 0.0090(14) -0.0040(16) C15 0.040(2) 0.073(3) 0.054(2) -0.018(2) 0.0161(17) -0.0139(19) C16 0.039(2) 0.097(3) 0.068(3) -0.025(3) 0.016(2) -0.019(2) C17 0.030(2) 0.095(3) 0.060(3) -0.013(2) 0.0214(18) -0.0026(19) C18 0.041(2) 0.099(4) 0.078(3) -0.036(3) 0.024(2) -0.006(2) C19 0.041(2) 0.077(3) 0.058(2) -0.024(2) 0.0175(18) -0.010(2) Br1 0.0398(3) 0.1327(6) 0.0910(5) -0.0280(3) 0.0316(3) -0.0090(3) P1 0.0848(9) 0.0516(6) 0.0412(6) 0.0049(4) 0.0006(5) 0.0026(5) F11 0.148(12) 0.072(5) 0.114(9) 0.006(5) -0.073(8) -0.001(6) F12 0.092(7) 0.044(5) 0.076(6) -0.003(4) 0.019(5) 0.002(4) F13 0.150(8) 0.093(5) 0.085(5) 0.027(4) 0.061(6) 0.042(5) F14 0.184(9) 0.056(3) 0.053(3) -0.001(3) -0.019(5) 0.022(5) F15 0.074(5) 0.147(10) 0.091(10) 0.066(8) 0.012(6) -0.015(5) F16 0.092(5) 0.086(5) 0.075(5) -0.001(4) -0.014(4) 0.014(4) F111 0.059(4) 0.076(6) 0.113(7) 0.042(5) 0.003(4) 0.003(3) F112 0.126(15) 0.056(9) 0.081(10) 0.013(6) -0.017(9) -0.027(8) F113 0.125(7) 0.074(4) 0.059(4) 0.010(3) 0.043(4) 0.000(4) F114 0.067(3) 0.053(3) 0.051(3) 0.010(2) -0.001(3) -0.013(3) F115 0.157(13) 0.083(5) 0.038(4) 0.010(3) 0.015(6) 0.022(7) F116 0.059(4) 0.115(7) 0.114(7) 0.046(6) 0.005(5) 0.006(5) C21 0.114(11) 0.123(11) 0.76(6) 0.20(2) 0.18(2) 0.051(9) C22 0.132(7) 0.046(3) 0.065(4) 0.017(3) 0.061(4) 0.018(4) C23 0.56(5) 0.085(8) 0.087(8) -0.001(6) -0.088(15) 0.082(15) O24 0.099(4) 0.072(3) 0.061(3) 0.009(2) 0.032(3) 0.027(3) O34 0.034(5) 0.067(7) 0.082(8) -0.035(6) 0.002(5) -0.007(5) C32 0.015(9) 0.046(9) 0.079(12) -0.002(7) -0.005(8) 0.000(7) C31 0.15(2) 0.083(15) 0.098(17) 0.032(13) -0.001(16) -0.007(15) C33 0.027(10) 0.054(10) 0.090(13) -0.016(8) -0.006(10) 0.021(9) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag Cu1 N2 . . 1.951(3) Y Cu1 N2 . 2 1.951(3) Y Cu1 N1 . 2 2.205(3) Y Cu1 N1 . . 2.205(3) Y Cu1 N3 . . 2.230(3) Y Cu1 N3 . 2 2.230(3) Y N1 C1 . . 1.337(5) Y N1 C5 . . 1.347(4) Y N2 C8 . . 1.346(5) Y N2 C6 . . 1.346(4) Y N3 C13 . . 1.336(5) Y N3 C9 . . 1.346(5) Y N4 C6 . . 1.321(4) Y N4 C7 . . 1.346(5) Y N5 C8 . . 1.303(5) Y N5 C7 . . 1.357(5) Y C1 C2 . . 1.379(6) Y C1 H1 . . 0.95 ? C2 C3 . . 1.379(6) Y C2 H2 . . 0.95 ? C3 C4 . . 1.386(5) Y C3 H3 . . 0.95 ? C4 C5 . . 1.377(5) Y C4 H4 . . 0.95 ? C5 C6 . . 1.482(5) Y C7 C14 . . 1.457(5) Y C8 C9 . . 1.482(5) Y C9 C10 . . 1.387(5) Y C10 C11 . . 1.388(6) Y C10 H10 . . 0.95 ? C11 C12 . . 1.389(8) Y C11 H11 . . 0.95 ? C12 C13 . . 1.398(8) Y C12 H12 . . 0.95 ? C13 H13 . . 0.95 ? C14 C19 . . 1.390(6) Y C14 C15 . . 1.390(6) Y C15 C16 . . 1.373(6) Y C15 H15 . . 0.95 ? C16 C17 . . 1.369(7) Y C16 H16 . . 0.95 ? C17 C18 . . 1.380(7) Y C17 Br1 . . 1.898(4) Y C18 C19 . . 1.376(6) Y C18 H18 . . 0.95 ? C19 H19 . . 0.95 ? P1 F11 . . 1.466(9) Y P1 F15 . . 1.480(13) Y P1 F112 . . 1.49(2) Y P1 F116 . . 1.503(8) Y P1 F113 . . 1.552(6) Y P1 F14 . . 1.570(6) Y P1 F115 . . 1.587(12) Y P1 F12 . . 1.65(2) Y P1 F16 . . 1.658(9) Y P1 F111 . . 1.676(9) Y P1 F114 . . 1.677(5) Y P1 F13 . . 1.743(8) Y C21 C22 . . 1.330(18) Y C21 H21a . . 0.98 ? C21 H21b . . 0.98 ? C21 H21c . . 0.98 ? C22 O24 . . 1.127(8) Y C22 C23 . . 1.53(2) Y C23 H23a . . 0.98 ? C23 H23b . . 0.98 ? C23 H23c . . 0.98 ? O34 C32 . . 1.13(2) Y C32 C31 . . 1.41(3) Y C32 C33 . . 1.44(2) Y C31 H31a . . 0.98 ? C31 H31b . . 0.98 ? C31 H31c . . 0.98 ? C33 H33a . . 0.98 ? C33 H33b . . 0.98 ? C33 H33c . . 0.98 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_2 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag N2 CU1 N2 . . 2 176.89(16) Y N2 CU1 N1 . . 2 105.68(11) Y N2 CU1 N1 2 . 2 76.59(11) Y N2 CU1 N1 . . . 76.59(11) Y N2 CU1 N1 2 . . 105.68(11) Y N1 CU1 N1 2 . . 90.00(16) Y N2 CU1 N3 . . . 76.58(11) Y N2 CU1 N3 2 . . 101.25(11) Y N1 CU1 N3 2 . . 94.14(11) Y N1 CU1 N3 . . . 152.98(11) Y N2 CU1 N3 . . 2 101.25(11) Y N2 CU1 N3 2 . 2 76.58(11) Y N1 CU1 N3 2 . 2 152.98(11) Y N1 CU1 N3 . . 2 94.14(11) Y N3 CU1 N3 . . 2 94.17(17) Y C1 N1 C5 . . . 117.9(3) Y C1 N1 CU1 . . . 129.1(3) Y C5 N1 CU1 . . . 113.0(2) Y C8 N2 C6 . . . 116.3(3) Y C8 N2 CU1 . . . 122.1(2) Y C6 N2 CU1 . . . 121.6(2) Y C13 N3 C9 . . . 118.1(4) Y C13 N3 CU1 . . . 129.7(3) Y C9 N3 CU1 . . . 112.2(2) Y C6 N4 C7 . . . 115.6(3) Y C8 N5 C7 . . . 115.8(3) Y N1 C1 C2 . . . 122.3(4) Y N1 C1 H1 . . . 118.9 ? C2 C1 H1 . . . 118.9 ? C3 C2 C1 . . . 119.3(4) Y C3 C2 H2 . . . 120.3 ? C1 C2 H2 . . . 120.3 ? C2 C3 C4 . . . 119.1(4) Y C2 C3 H3 . . . 120.4 ? C4 C3 H3 . . . 120.4 ? C5 C4 C3 . . . 118.0(4) Y C5 C4 H4 . . . 121 ? C3 C4 H4 . . . 121 ? N1 C5 C4 . . . 123.3(3) Y N1 C5 C6 . . . 113.9(3) Y C4 C5 C6 . . . 122.7(3) Y N4 C6 N2 . . . 123.9(3) Y N4 C6 C5 . . . 121.8(3) Y N2 C6 C5 . . . 114.4(3) Y N4 C7 N5 . . . 124.2(3) Y N4 C7 C14 . . . 118.7(3) Y N5 C7 C14 . . . 117.1(3) Y N5 C8 N2 . . . 124.3(3) Y N5 C8 C9 . . . 121.3(3) Y N2 C8 C9 . . . 114.4(3) Y N3 C9 C10 . . . 123.8(3) Y N3 C9 C8 . . . 114.7(3) Y C10 C9 C8 . . . 121.5(3) Y C9 C10 C11 . . . 117.8(4) Y C9 C10 H10 . . . 121.1 ? C11 C10 H10 . . . 121.1 ? C10 C11 C12 . . . 119.0(4) Y C10 C11 H11 . . . 120.5 ? C12 C11 H11 . . . 120.5 ? C11 C12 C13 . . . 119.3(4) Y C11 C12 H12 . . . 120.4 ? C13 C12 H12 . . . 120.4 ? N3 C13 C12 . . . 122.0(4) Y N3 C13 H13 . . . 119 ? C12 C13 H13 . . . 119 ? C19 C14 C15 . . . 118.7(4) Y C19 C14 C7 . . . 119.9(4) Y C15 C14 C7 . . . 121.4(4) Y C16 C15 C14 . . . 120.9(4) Y C16 C15 H15 . . . 119.5 ? C14 C15 H15 . . . 119.5 ? C17 C16 C15 . . . 119.2(4) Y C17 C16 H16 . . . 120.4 ? C15 C16 H16 . . . 120.4 ? C16 C17 C18 . . . 121.3(4) Y C16 C17 BR1 . . . 119.4(3) Y C18 C17 BR1 . . . 119.3(3) Y C19 C18 C17 . . . 119.2(4) Y C19 C18 H18 . . . 120.4 ? C17 C18 H18 . . . 120.4 ? C18 C19 C14 . . . 120.5(4) Y C18 C19 H19 . . . 119.7 ? C14 C19 H19 . . . 119.7 ? F11 P1 F15 . . . 99.7(8) Y F11 P1 F112 . . . 96.50(11) Y F15 P1 F112 . . . 104.8(1) Y F11 P1 F116 . . . 146.6(7) Y F15 P1 F116 . . . 105.8(6) Y F112 P1 F116 . . . 97.3(1) Y F11 P1 F113 . . . 56.2(6) Y F15 P1 F113 . . . 151.8(6) Y F112 P1 F113 . . . 93.4(9) Y F116 P1 F113 . . . 92.7(6) Y F11 P1 F14 . . . 94.2(5) Y F15 P1 F14 . . . 99.6(8) Y F112 P1 F14 . . . 151.2(9) Y F116 P1 F14 . . . 60.9(6) Y F113 P1 F14 . . . 70.7(4) Y F11 P1 F115 . . . 118.9(8) Y F15 P1 F115 . . . 20.4(7) Y F112 P1 F115 . . . 94.6(1) Y F116 P1 F115 . . . 90.0(6) Y F113 P1 F115 . . . 171.1(6) Y F14 P1 F115 . . . 103.4(6) Y F11 P1 F12 . . . 92.10(11) Y F15 P1 F12 . . . 91.2(1) Y F112 P1 F12 . . . 15.30(13) Y F116 P1 F12 . . . 108.3(1) Y F113 P1 F12 . . . 103.2(9) Y F14 P1 F12 . . . 166.4(9) Y F115 P1 F12 . . . 83.9(1) Y F11 P1 F16 . . . 172.3(7) Y F15 P1 F16 . . . 87.7(6) Y F112 P1 F16 . . . 79.6(1) Y F116 P1 F16 . . . 29.6(4) Y F113 P1 F16 . . . 117.1(5) Y F14 P1 F16 . . . 86.5(4) Y F115 P1 F16 . . . 68.2(6) Y F12 P1 F16 . . . 85.7(1) Y F11 P1 F111 . . . 30.3(6) Y F15 P1 F111 . . . 73.1(6) Y F112 P1 F111 . . . 89.5(9) Y F116 P1 F111 . . . 173.1(5) Y F113 P1 F111 . . . 86.0(5) Y F14 P1 F111 . . . 112.3(5) Y F115 P1 F111 . . . 90.3(6) Y F12 P1 F111 . . . 78.6(1) Y F16 P1 F111 . . . 154.7(5) Y F11 P1 F114 . . . 78.3(5) Y F15 P1 F114 . . . 69.1(7) Y F112 P1 F114 . . . 171.0(8) Y F116 P1 F114 . . . 90.9(4) Y F113 P1 F114 . . . 89.9(4) Y F14 P1 F114 . . . 37.6(4) Y F115 P1 F114 . . . 81.6(5) Y F12 P1 F114 . . . 155.9(8) Y F16 P1 F114 . . . 106.4(4) Y F111 P1 F114 . . . 82.3(4) Y F11 P1 F13 . . . 88.0(7) Y F15 P1 F13 . . . 169.2(7) Y F112 P1 F13 . . . 66.5(8) Y F116 P1 F13 . . . 70.1(5) Y F113 P1 F13 . . . 38.7(4) Y F14 P1 F13 . . . 87.3(5) Y F115 P1 F13 . . . 149.5(7) Y F12 P1 F13 . . . 80.9(8) Y F16 P1 F13 . . . 84.4(5) Y F111 P1 F13 . . . 112.2(5) Y F114 P1 F13 . . . 120.2(4) Y O24 C22 C21 . . . 129.70(15) Y O24 C22 C23 . . . 111.10(11) Y C21 C22 C23 . . . 119.00(15) Y O34 C32 C31 . . . 126(2) Y O34 C32 C33 . . . 117(2) Y C31 C32 C33 . . . 117(2) Y C32 C31 H31A . . . 109.5 ? C32 C31 H31B . . . 109.5 ? H31A C31 H31B . . . 109.5 ? C32 C31 H31C . . . 109.5 ? H31A C31 H31C . . . 109.5 ? H31B C31 H31C . . . 109.5 ? C32 C33 H33A . . . 109.5 ? C32 C33 H33B . . . 109.5 ? H33A C33 H33B . . . 109.5 ? C32 C33 H33C . . . 109.5 ? H33A C33 H33C . . . 109.5 ? H33B C33 H33C . . . 109.5 ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion _geom_torsion_publ_flag N2 CU1 N1 C1 . . . . 174.8(3) N N2 CU1 N1 C1 2 . . . -7.4(3) N N1 CU1 N1 C1 2 . . . 68.6(3) N N3 CU1 N1 C1 . . . . 167.8(3) N N3 CU1 N1 C1 2 . . . -84.6(3) N N2 CU1 N1 C5 . . . . -6.3(2) N N2 CU1 N1 C5 2 . . . 171.5(2) N N1 CU1 N1 C5 2 . . . -112.4(3) N N3 CU1 N1 C5 . . . . -13.3(4) N N3 CU1 N1 C5 2 . . . 94.3(2) N N2 CU1 N2 C8 2 . . . 46.1(3) N N1 CU1 N2 C8 2 . . . -90.6(3) N N1 CU1 N2 C8 . . . . -176.8(3) N N3 CU1 N2 C8 . . . . 0.0(3) N N3 CU1 N2 C8 2 . . . 91.6(3) N N2 CU1 N2 C6 2 . . . -130.7(2) N N1 CU1 N2 C6 2 . . . 92.6(3) N N1 CU1 N2 C6 . . . . 6.5(2) N N3 CU1 N2 C6 . . . . -176.8(3) N N3 CU1 N2 C6 2 . . . -85.1(3) N N2 CU1 N3 C13 . . . . 178.4(4) N N2 CU1 N3 C13 2 . . . 0.7(4) N N1 CU1 N3 C13 2 . . . -76.4(4) N N1 CU1 N3 C13 . . . . -174.6(4) N N3 CU1 N3 C13 2 . . . 77.8(4) N N2 CU1 N3 C9 . . . . -0.4(2) N N2 CU1 N3 C9 2 . . . -178.1(3) N N1 CU1 N3 C9 2 . . . 104.7(3) N N1 CU1 N3 C9 . . . . 6.6(4) N N3 CU1 N3 C9 2 . . . -101.0(3) N C5 N1 C1 C2 . . . . -2.0(6) N CU1 N1 C1 C2 . . . . 176.9(3) N N1 C1 C2 C3 . . . . 0.8(6) N C1 C2 C3 C4 . . . . 0.9(6) N C2 C3 C4 C5 . . . . -1.3(6) N C1 N1 C5 C4 . . . . 1.7(5) N CU1 N1 C5 C4 . . . . -177.4(3) N C1 N1 C5 C6 . . . . -175.6(3) N CU1 N1 C5 C6 . . . . 5.3(3) N C3 C4 C5 N1 . . . . 0.0(5) N C3 C4 C5 C6 . . . . 177.0(3) N C7 N4 C6 N2 . . . . 3.1(5) N C7 N4 C6 C5 . . . . -176.0(3) N C8 N2 C6 N4 . . . . -1.7(5) N CU1 N2 C6 N4 . . . . 175.2(2) N C8 N2 C6 C5 . . . . 177.4(3) N CU1 N2 C6 C5 . . . . -5.6(4) N N1 C5 C6 N4 . . . . 178.7(3) N C4 C5 C6 N4 . . . . 1.4(5) N N1 C5 C6 N2 . . . . -0.5(4) N C4 C5 C6 N2 . . . . -177.8(3) N C6 N4 C7 N5 . . . . -1.1(5) N C6 N4 C7 C14 . . . . -179.5(3) N C8 N5 C7 N4 . . . . -2.1(5) N C8 N5 C7 C14 . . . . 176.3(3) N C7 N5 C8 N2 . . . . 3.7(5) N C7 N5 C8 C9 . . . . -175.6(3) N C6 N2 C8 N5 . . . . -1.9(5) N CU1 N2 C8 N5 . . . . -178.9(3) N C6 N2 C8 C9 . . . . 177.4(3) N CU1 N2 C8 C9 . . . . 0.4(4) N C13 N3 C9 C10 . . . . 0.1(6) N CU1 N3 C9 C10 . . . . 179.1(3) N C13 N3 C9 C8 . . . . -178.2(4) N CU1 N3 C9 C8 . . . . 0.8(4) N N5 C8 C9 N3 . . . . 178.5(3) N N2 C8 C9 N3 . . . . -0.8(5) N N5 C8 C9 C10 . . . . 0.2(6) N N2 C8 C9 C10 . . . . -179.2(4) N N3 C9 C10 C11 . . . . -1.2(7) N C8 C9 C10 C11 . . . . 177.0(4) N C9 C10 C11 C12 . . . . 1.1(8) N C10 C11 C12 C13 . . . . -0.1(9) N C9 N3 C13 C12 . . . . 1.0(7) N CU1 N3 C13 C12 . . . . -177.7(4) N C11 C12 C13 N3 . . . . -1.0(9) N N4 C7 C14 C19 . . . . 167.2(4) N N5 C7 C14 C19 . . . . -11.2(6) N N4 C7 C14 C15 . . . . -11.2(6) N N5 C7 C14 C15 . . . . 170.4(4) N C19 C14 C15 C16 . . . . -0.7(7) N C7 C14 C15 C16 . . . . 177.7(5) N C14 C15 C16 C17 . . . . 0.4(8) N C15 C16 C17 C18 . . . . -0.2(9) N C15 C16 C17 BR1 . . . . 178.7(4) N C16 C17 C18 C19 . . . . 0.4(9) N BR1 C17 C18 C19 . . . . -178.5(4) N C17 C18 C19 C14 . . . . -0.8(9) N C15 C14 C19 C18 . . . . 1.0(7) N C7 C14 C19 C18 . . . . -177.5(5) N _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 68.88 _diffrn_measured_fraction_theta_full 0.987 _refine_diff_density_max 1.906 _refine_diff_density_min -1.428 _refine_diff_density_rms 0.106 # Attachment '611629.cif' data_gar119 _database_code_depnum_ccdc_archive 'CCDC 611629' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C40 H30 Fe N10, 2(F6 P)' _chemical_formula_sum 'C40 H30 F12 Fe N10 P2' _chemical_formula_weight 996.53 _chemical_compound_source 'Synthesized by the authors. See text' 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 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Fe Fe -1.1336 3.1974 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21/n _symmetry_space_group_name_hall '-P 2yn' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 8.9622(3) _cell_length_b 33.0144(8) _cell_length_c 13.3712(4) _cell_angle_alpha 90.00 _cell_angle_beta 92.053(2) _cell_angle_gamma 90.00 _cell_volume 3953.8(2) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 16615 _cell_measurement_theta_min 2.68 _cell_measurement_theta_max 68.70 _exptl_crystal_description Needle _exptl_crystal_colour purple _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.04 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.674 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2016 _exptl_absorpt_coefficient_mu 4.763 _exptl_absorpt_correction_Type multi-scan _exptl_absorpt_correction_T_min 0.68 _exptl_absorpt_correction_T_max 0.91 _exptl_absorpt_process_details 'Sadabs (Sheldrick,1996)' _exptl_special_details ; X-ray crystallographic data for I were collected from a single crystal sample, which was mounted on a loop fiber. Data were collected using a Bruker Platform diffractometer, equipped with a Bruker SMART 4K Charged-Coupled Device (CCD) Area Detector using the program SMART and a rotating anode source Cu-K\a radiation. The crystal-to-detector distance was 5.120 cm, and the data collection was carried out in 512 x 512 pixel mode, utilizing 4 x 4 pixel binning. The initial unit cell parameters were determined by a least-squares fit of the angular setting of strong reflections, collected by a 9.0 degree scan in 30 frames over four different parts of the reciprocal space (120 frames total). Upon completion of the data collection, the first 101 frames were recollected in order to improve the decay correction analysis. ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'Rotating Anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker AXS Smart 4K/Platform' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 5.5 _diffrn_standards_number 237 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0.42 _diffrn_reflns_number 54135 _diffrn_reflns_av_R_equivalents 0.034 _diffrn_reflns_av_sigmaI/netI 0.0238 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -39 _diffrn_reflns_limit_k_max 39 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.68 _diffrn_reflns_theta_max 68.97 _reflns_number_total 7253 _reflns_number_gt 6191 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'SMART (Bruker, 2001)' _computing_cell_refinement 'SMART (Bruker, 2001)' _computing_data_reduction 'SAINT (Bruker, 2003)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL (Bruker, 1997)' _computing_publication_material 'UdMX (local program)' _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^)+(0.0675P)^2^+2.1395P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 7253 _refine_ls_number_parameters 588 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0477 _refine_ls_R_factor_gt 0.0380 _refine_ls_wR_factor_ref 0.1096 _refine_ls_wR_factor_gt 0.0988 _refine_ls_goodness_of_fit_ref 1.002 _refine_ls_restrained_S_all 1.002 _refine_ls_shift/su_max 0.000 _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 Fe1 Fe 0.48022(4) 0.117747(10) 0.81119(2) 0.02472(11) Uani 1 1 d . . . N1 N 0.5800(2) 0.10735(5) 0.94542(13) 0.0263(4) Uani 1 1 d . . . N2 N 0.5176(2) 0.06205(5) 0.80117(13) 0.0270(4) Uani 1 1 d . . . N3 N 0.3898(2) 0.10626(6) 0.67461(14) 0.0286(4) Uani 1 1 d . . . N4 N 0.6113(2) 0.00202(5) 0.87430(14) 0.0292(4) Uani 1 1 d . . . N5 N 0.4973(2) 0.00165(6) 0.70903(14) 0.0297(4) Uani 1 1 d . . . N6 N 0.2780(2) 0.11652(5) 0.87140(14) 0.0289(4) Uani 1 1 d . . . N7 N 0.4432(2) 0.17355(5) 0.82281(13) 0.0271(4) Uani 1 1 d . . . N8 N 0.6681(2) 0.14061(5) 0.75674(13) 0.0265(4) Uani 1 1 d . . . N9 N 0.2909(2) 0.22548(6) 0.88118(14) 0.0318(4) Uani 1 1 d . . . N10 N 0.5232(2) 0.24107(6) 0.80618(14) 0.0303(4) Uani 1 1 d . . . C1 C 0.6077(2) 0.13402(7) 1.01930(17) 0.0296(5) Uani 1 1 d . . . H1 H 0.5759 0.1613 1.0102 0.036 Uiso 1 1 calc R . . C2 C 0.6813(3) 0.12342(7) 1.10871(18) 0.0330(5) Uani 1 1 d . . . H2 H 0.6987 0.1431 1.1596 0.040 Uiso 1 1 calc R . . C3 C 0.7289(3) 0.08408(7) 1.12306(18) 0.0357(5) Uani 1 1 d . . . H3 H 0.7806 0.0764 1.1834 0.043 Uiso 1 1 calc R . . C4 C 0.7001(3) 0.05577(7) 1.04800(17) 0.0322(5) Uani 1 1 d . . . H4 H 0.7316 0.0285 1.0561 0.039 Uiso 1 1 calc R . . C5 C 0.6251(2) 0.06808(6) 0.96145(17) 0.0279(5) Uani 1 1 d . . . C6 C 0.5858(2) 0.04129(6) 0.87648(16) 0.0268(4) Uani 1 1 d . . . C7 C 0.5686(2) -0.01681(7) 0.78761(17) 0.0296(5) Uani 1 1 d . . . C8 C 0.4733(2) 0.04061(7) 0.71996(17) 0.0281(5) Uani 1 1 d . . . C9 C 0.3946(2) 0.06649(7) 0.64597(17) 0.0293(5) Uani 1 1 d . . . C10 C 0.3282(3) 0.05236(7) 0.55844(18) 0.0354(5) Uani 1 1 d . . . H10 H 0.3342 0.0245 0.5410 0.043 Uiso 1 1 calc R . . C11 C 0.2525(3) 0.07958(8) 0.49623(19) 0.0396(6) Uani 1 1 d . . . H11 H 0.2035 0.0707 0.4360 0.047 Uiso 1 1 calc R . . C12 C 0.2496(3) 0.12002(8) 0.52347(19) 0.0385(6) Uani 1 1 d . . . H12 H 0.1999 0.1393 0.4812 0.046 Uiso 1 1 calc R . . C13 C 0.3190(3) 0.13232(7) 0.61226(18) 0.0327(5) Uani 1 1 d . . . H13 H 0.3166 0.1602 0.6298 0.039 Uiso 1 1 calc R . . C14 C 0.5981(3) -0.06019(7) 0.77941(17) 0.0311(5) Uani 1 1 d . . . C15 C 0.6927(3) -0.07970(7) 0.8481(2) 0.0401(6) Uani 1 1 d . . . H15 H 0.7430 -0.0645 0.8994 0.048 Uiso 1 1 calc R . . C16 C 0.7143(3) -0.12102(7) 0.8425(2) 0.0433(6) Uani 1 1 d . . . H16 H 0.7796 -0.1339 0.8903 0.052 Uiso 1 1 calc R . . C17 C 0.6431(3) -0.14418(7) 0.7689(2) 0.0407(6) Uani 1 1 d . . . C18 C 0.5536(3) -0.12436(8) 0.6982(2) 0.0441(6) Uani 1 1 d . . . H18 H 0.5060 -0.1395 0.6457 0.053 Uiso 1 1 calc R . . C19 C 0.5318(3) -0.08304(8) 0.70229(19) 0.0389(6) Uani 1 1 d . . . H19 H 0.4712 -0.0701 0.6521 0.047 Uiso 1 1 calc R . . C20 C 0.6575(4) -0.18967(8) 0.7678(2) 0.0536(7) Uani 1 1 d . . . H20A H 0.5643 -0.2019 0.7894 0.080 Uiso 1 1 calc R . . H20B H 0.7400 -0.1979 0.8134 0.080 Uiso 1 1 calc R . . H20C H 0.6774 -0.1988 0.6998 0.080 Uiso 1 1 calc R . . C21 C 0.1960(3) 0.08423(7) 0.89466(18) 0.0351(5) Uani 1 1 d . . . H21 H 0.2337 0.0579 0.8819 0.042 Uiso 1 1 calc R . . C22 C 0.0575(3) 0.08798(8) 0.9369(2) 0.0438(6) Uani 1 1 d . . . H22 H 0.0026 0.0644 0.9534 0.053 Uiso 1 1 calc R . . C23 C -0.0003(3) 0.12577(9) 0.9548(2) 0.0439(6) Uani 1 1 d . . . H23 H -0.0956 0.1286 0.9830 0.053 Uiso 1 1 calc R . . C24 C 0.0824(3) 0.15966(8) 0.93115(19) 0.0377(5) Uani 1 1 d . . . H24 H 0.0454 0.1861 0.9428 0.045 Uiso 1 1 calc R . . C25 C 0.2191(3) 0.15399(7) 0.89045(17) 0.0304(5) Uani 1 1 d . . . C26 C 0.3191(2) 0.18721(7) 0.86415(16) 0.0281(5) Uani 1 1 d . . . C27 C 0.3966(3) 0.25180(7) 0.85145(17) 0.0304(5) Uani 1 1 d . . . C28 C 0.5427(2) 0.20161(7) 0.79498(16) 0.0273(4) Uani 1 1 d . . . C29 C 0.6753(2) 0.18192(7) 0.75453(16) 0.0277(5) Uani 1 1 d . . . C30 C 0.7971(3) 0.20246(7) 0.72009(18) 0.0338(5) Uani 1 1 d . . . H30 H 0.7980 0.2312 0.7190 0.041 Uiso 1 1 calc R . . C31 C 0.9178(3) 0.18088(8) 0.68713(19) 0.0383(6) Uani 1 1 d . . . H31 H 1.0028 0.1945 0.6631 0.046 Uiso 1 1 calc R . . C32 C 0.9123(3) 0.13895(7) 0.68993(19) 0.0355(5) Uani 1 1 d . . . H32 H 0.9941 0.1234 0.6682 0.043 Uiso 1 1 calc R . . C33 C 0.7860(3) 0.11987(7) 0.72486(17) 0.0307(5) Uani 1 1 d . . . H33 H 0.7831 0.0911 0.7262 0.037 Uiso 1 1 calc R . . C34 C 0.3692(3) 0.29474(7) 0.87413(18) 0.0337(5) Uani 1 1 d . . . C35 C 0.2582(3) 0.30499(8) 0.94015(19) 0.0386(6) Uani 1 1 d . . . H35 H 0.1964 0.2845 0.9665 0.046 Uiso 1 1 calc R . . C36 C 0.2381(3) 0.34504(8) 0.9672(2) 0.0417(6) Uani 1 1 d . . . H36 H 0.1634 0.3516 1.0132 0.050 Uiso 1 1 calc R . . C37 C 0.3243(3) 0.37577(8) 0.9287(2) 0.0404(6) Uani 1 1 d . . . C38 C 0.4310(3) 0.36538(7) 0.8596(2) 0.0390(6) Uani 1 1 d . . . H38 H 0.4883 0.3861 0.8301 0.047 Uiso 1 1 calc R . . C39 C 0.4547(3) 0.32537(7) 0.83302(19) 0.0367(5) Uani 1 1 d . . . H39 H 0.5291 0.3188 0.7868 0.044 Uiso 1 1 calc R . . C40 C 0.3052(4) 0.41911(8) 0.9629(2) 0.0512(7) Uani 1 1 d . . . H40A H 0.2121 0.4216 0.9987 0.077 Uiso 1 1 calc R . . H40B H 0.3015 0.4371 0.9045 0.077 Uiso 1 1 calc R . . H40C H 0.3897 0.4267 1.0075 0.077 Uiso 1 1 calc R . . P1 P -0.00257(7) 0.005136(19) 0.72110(5) 0.03879(16) Uani 1 1 d . . . F11 F -0.0401(2) -0.04195(5) 0.72380(14) 0.0604(5) Uani 1 1 d . . . F12 F -0.1729(2) 0.01532(6) 0.69300(18) 0.0733(6) Uani 1 1 d . . . F13 F -0.0383(2) 0.00812(6) 0.83707(14) 0.0719(6) Uani 1 1 d . . . F14 F 0.16713(19) -0.00385(5) 0.75239(16) 0.0672(5) Uani 1 1 d . . . F15 F 0.0329(2) 0.00240(6) 0.60711(14) 0.0668(5) Uani 1 1 d . . . F16 F 0.03573(19) 0.05268(5) 0.71865(13) 0.0515(4) Uani 1 1 d . . . P2 P 0.77894(7) 0.247359(19) 0.05248(5) 0.03570(16) Uani 1 1 d . . . F21 F 0.7194(2) 0.28551(5) -0.00972(13) 0.0616(5) Uani 1 1 d . . . F22 F 0.8046(2) 0.22290(6) -0.04804(14) 0.0727(6) Uani 1 1 d . . . F23 F 0.6120(2) 0.23032(6) 0.05189(15) 0.0646(5) Uani 1 1 d . . . F24 F 0.74991(19) 0.27145(5) 0.15400(11) 0.0488(4) Uani 1 1 d . . . F25 F 0.9427(2) 0.26541(7) 0.05406(16) 0.0734(6) Uani 1 1 d . . . F26 F 0.8373(2) 0.20960(5) 0.11519(14) 0.0700(6) 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 Fe1 0.02470(19) 0.01974(18) 0.02970(19) -0.00018(13) 0.00089(13) 0.00009(12) N1 0.0239(9) 0.0251(9) 0.0299(9) 0.0003(7) 0.0024(7) -0.0011(7) N2 0.0264(9) 0.0242(9) 0.0305(10) 0.0002(7) 0.0013(7) -0.0025(7) N3 0.0270(10) 0.0259(9) 0.0329(10) 0.0004(8) 0.0012(7) 0.0005(7) N4 0.0316(10) 0.0231(9) 0.0332(10) 0.0001(7) 0.0034(8) -0.0004(7) N5 0.0291(10) 0.0249(10) 0.0351(10) -0.0016(8) 0.0004(8) -0.0002(7) N6 0.0265(10) 0.0289(10) 0.0312(10) -0.0006(7) -0.0003(7) -0.0001(7) N7 0.0273(10) 0.0246(9) 0.0294(9) 0.0001(7) -0.0008(7) 0.0008(7) N8 0.0271(10) 0.0233(9) 0.0292(9) 0.0007(7) 0.0000(7) -0.0006(7) N9 0.0336(11) 0.0274(10) 0.0342(10) -0.0013(8) -0.0011(8) 0.0049(8) N10 0.0329(10) 0.0244(10) 0.0331(10) -0.0011(7) -0.0042(8) 0.0015(8) C1 0.0279(12) 0.0258(11) 0.0353(12) -0.0019(9) 0.0033(9) -0.0018(9) C2 0.0340(13) 0.0328(12) 0.0325(12) -0.0055(9) 0.0041(9) -0.0051(9) C3 0.0371(13) 0.0380(13) 0.0319(12) 0.0043(10) -0.0009(10) -0.0049(10) C4 0.0337(12) 0.0276(11) 0.0353(12) 0.0055(9) 0.0012(9) -0.0013(9) C5 0.0271(11) 0.0239(11) 0.0329(12) 0.0013(9) 0.0039(8) -0.0024(8) C6 0.0240(11) 0.0255(11) 0.0309(11) 0.0006(9) 0.0033(8) -0.0019(8) C7 0.0266(11) 0.0272(11) 0.0353(12) 0.0000(9) 0.0041(9) -0.0027(9) C8 0.0235(11) 0.0273(11) 0.0335(12) -0.0014(9) 0.0025(8) -0.0027(8) C9 0.0272(12) 0.0267(11) 0.0342(12) -0.0003(9) 0.0022(9) -0.0009(8) C10 0.0374(13) 0.0323(12) 0.0365(13) -0.0035(10) -0.0016(10) -0.0013(10) C11 0.0411(14) 0.0433(15) 0.0338(13) -0.0023(11) -0.0048(10) -0.0001(11) C12 0.0386(14) 0.0391(14) 0.0373(13) 0.0043(10) -0.0053(10) 0.0048(10) C13 0.0337(12) 0.0282(12) 0.0363(12) 0.0035(10) 0.0012(9) 0.0031(9) C14 0.0321(12) 0.0255(11) 0.0359(12) -0.0001(9) 0.0065(9) 0.0001(9) C15 0.0459(15) 0.0297(13) 0.0444(14) 0.0008(11) -0.0031(11) -0.0007(10) C16 0.0499(16) 0.0299(13) 0.0498(16) 0.0056(11) 0.0005(12) 0.0043(11) C17 0.0456(15) 0.0272(13) 0.0501(15) 0.0004(11) 0.0146(12) 0.0028(10) C18 0.0528(16) 0.0345(14) 0.0453(15) -0.0115(11) 0.0036(12) -0.0024(12) C19 0.0453(15) 0.0324(13) 0.0389(13) -0.0017(10) 0.0018(11) 0.0025(10) C20 0.065(2) 0.0288(14) 0.0680(19) -0.0021(13) 0.0154(15) 0.0021(12) C21 0.0329(13) 0.0305(12) 0.0419(13) -0.0002(10) 0.0023(10) -0.0052(9) C22 0.0363(14) 0.0457(15) 0.0498(15) 0.0010(12) 0.0055(11) -0.0101(11) C23 0.0264(13) 0.0543(16) 0.0512(16) 0.0000(13) 0.0069(11) -0.0019(11) C24 0.0313(13) 0.0421(14) 0.0397(13) -0.0024(11) 0.0011(10) 0.0048(10) C25 0.0285(12) 0.0312(12) 0.0314(12) 0.0004(9) -0.0032(9) 0.0010(9) C26 0.0277(12) 0.0273(11) 0.0290(11) -0.0002(9) -0.0021(8) 0.0042(8) C27 0.0330(12) 0.0263(11) 0.0314(12) -0.0026(9) -0.0070(9) 0.0050(9) C28 0.0307(12) 0.0231(11) 0.0279(11) 0.0002(8) -0.0027(8) -0.0005(8) C29 0.0288(11) 0.0234(11) 0.0305(11) 0.0004(9) -0.0026(8) 0.0005(8) C30 0.0370(13) 0.0249(11) 0.0397(13) 0.0007(10) 0.0028(10) -0.0039(9) C31 0.0315(13) 0.0383(13) 0.0453(14) 0.0033(11) 0.0051(10) -0.0050(10) C32 0.0305(13) 0.0344(13) 0.0420(13) 0.0021(10) 0.0061(10) 0.0038(10) C33 0.0322(12) 0.0252(11) 0.0345(12) 0.0008(9) 0.0008(9) 0.0034(9) C34 0.0376(13) 0.0271(12) 0.0358(12) -0.0026(10) -0.0086(10) 0.0046(9) C35 0.0443(15) 0.0313(13) 0.0400(14) -0.0050(10) -0.0004(11) 0.0037(10) C36 0.0466(15) 0.0367(14) 0.0419(14) -0.0078(11) 0.0014(11) 0.0055(11) C37 0.0443(15) 0.0323(13) 0.0437(14) -0.0052(11) -0.0107(11) 0.0067(11) C38 0.0392(14) 0.0297(13) 0.0475(15) 0.0020(11) -0.0075(11) -0.0010(10) C39 0.0368(14) 0.0326(13) 0.0403(13) -0.0006(10) -0.0050(10) 0.0036(10) C40 0.0603(19) 0.0311(14) 0.0618(18) -0.0082(13) -0.0033(14) 0.0063(12) P1 0.0344(4) 0.0308(3) 0.0512(4) 0.0002(3) 0.0034(3) -0.0013(2) F11 0.0689(12) 0.0355(9) 0.0774(12) -0.0026(8) 0.0090(9) -0.0122(8) F12 0.0401(10) 0.0697(13) 0.1098(17) 0.0152(11) -0.0010(10) -0.0008(8) F13 0.0967(16) 0.0609(12) 0.0591(11) -0.0061(9) 0.0165(10) -0.0188(10) F14 0.0429(10) 0.0507(10) 0.1073(16) 0.0284(10) -0.0067(9) 0.0023(8) F15 0.0890(14) 0.0546(11) 0.0577(11) -0.0043(8) 0.0144(10) -0.0059(9) F16 0.0557(10) 0.0314(8) 0.0672(11) 0.0042(7) -0.0012(8) -0.0005(7) P2 0.0377(4) 0.0323(3) 0.0368(3) -0.0056(3) -0.0035(2) 0.0056(2) F21 0.0876(14) 0.0443(9) 0.0515(10) 0.0048(7) -0.0184(9) 0.0071(9) F22 0.0774(13) 0.0886(14) 0.0511(10) -0.0311(10) -0.0116(9) 0.0381(11) F23 0.0497(10) 0.0567(11) 0.0871(13) -0.0152(9) -0.0034(9) -0.0111(8) F24 0.0605(10) 0.0461(9) 0.0397(8) -0.0089(7) 0.0006(7) 0.0047(7) F25 0.0437(10) 0.0990(16) 0.0778(13) -0.0022(11) 0.0062(9) -0.0108(10) F26 0.1026(16) 0.0375(9) 0.0676(12) -0.0004(8) -0.0280(11) 0.0162(9) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag Fe1 N2 . . 1.8747(18) Y Fe1 N7 . . 1.8792(18) Y Fe1 N1 . . 2.0059(18) Y Fe1 N8 . . 2.0061(19) Y Fe1 N3 . . 2.0076(19) Y Fe1 N6 . . 2.0093(19) Y N1 C1 . . 1.340(3) Y N1 C5 . . 1.373(3) Y N2 C8 . . 1.344(3) Y N2 C6 . . 1.347(3) Y N3 C13 . . 1.342(3) Y N3 C9 . . 1.369(3) Y N4 C6 . . 1.317(3) Y N4 C7 . . 1.359(3) Y N5 C8 . . 1.313(3) Y N5 C7 . . 1.355(3) Y N6 C21 . . 1.338(3) Y N6 C25 . . 1.373(3) Y N7 C26 . . 1.338(3) Y N7 C28 . . 1.348(3) Y N8 C33 . . 1.341(3) Y N8 C29 . . 1.366(3) Y N9 C26 . . 1.310(3) Y N9 C27 . . 1.356(3) Y N10 C28 . . 1.324(3) Y N10 C27 . . 1.352(3) Y C1 C2 . . 1.389(3) Y C1 H1 . . 0.95 ? C2 C3 . . 1.378(3) Y C2 H2 . . 0.95 ? C3 C4 . . 1.389(3) Y C3 H3 . . 0.95 ? C4 C5 . . 1.379(3) Y C4 H4 . . 0.95 ? C5 C6 . . 1.473(3) Y C7 C14 . . 1.461(3) Y C8 C9 . . 1.469(3) Y C9 C10 . . 1.375(3) Y C10 C11 . . 1.386(4) Y C10 H10 . . 0.95 ? C11 C12 . . 1.385(4) Y C11 H11 . . 0.95 ? C12 C13 . . 1.382(3) Y C12 H12 . . 0.95 ? C13 H13 . . 0.95 ? C14 C15 . . 1.387(3) Y C14 C19 . . 1.393(3) Y C15 C16 . . 1.380(3) Y C15 H15 . . 0.95 ? C16 C17 . . 1.385(4) Y C16 H16 . . 0.95 ? C17 C18 . . 1.382(4) Y C17 C20 . . 1.507(3) Y C18 C19 . . 1.379(4) Y C18 H18 . . 0.95 ? C19 H19 . . 0.95 ? C20 H20a . . 0.98 ? C20 H20b . . 0.98 ? C20 H20c . . 0.98 ? C21 C22 . . 1.388(4) Y C21 H21 . . 0.95 ? C22 C23 . . 1.375(4) Y C22 H22 . . 0.95 ? C23 C24 . . 1.385(4) Y C23 H23 . . 0.95 ? C24 C25 . . 1.371(3) Y C24 H24 . . 0.95 ? C25 C26 . . 1.467(3) Y C27 C34 . . 1.472(3) Y C28 C29 . . 1.474(3) Y C29 C30 . . 1.378(3) Y C30 C31 . . 1.381(4) Y C30 H30 . . 0.95 ? C31 C32 . . 1.386(3) Y C31 H31 . . 0.95 ? C32 C33 . . 1.391(3) Y C32 H32 . . 0.95 ? C33 H33 . . 0.95 ? C34 C39 . . 1.393(4) Y C34 C35 . . 1.395(4) Y C35 C36 . . 1.384(3) Y C35 H35 . . 0.95 ? C36 C37 . . 1.386(4) Y C36 H36 . . 0.95 ? C37 C38 . . 1.396(4) Y C37 C40 . . 1.513(3) Y C38 C39 . . 1.386(3) Y C38 H38 . . 0.95 ? C39 H39 . . 0.95 ? C40 H40a . . 0.98 ? C40 H40b . . 0.98 ? C40 H40c . . 0.98 ? P1 F15 . . 1.571(2) Y P1 F14 . . 1.5907(18) Y P1 F11 . . 1.5912(17) Y P1 F12 . . 1.5944(19) Y P1 F13 . . 1.598(2) Y P1 F16 . . 1.6073(16) Y P2 F26 . . 1.5810(17) Y P2 F25 . . 1.5836(19) Y P2 F21 . . 1.5909(17) Y P2 F22 . . 1.5917(17) Y P2 F23 . . 1.5986(18) Y P2 F24 . . 1.6026(16) Y loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_2 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag N2 FE1 N7 . . . 179.35(8) Y N2 FE1 N1 . . . 79.70(8) Y N7 FE1 N1 . . . 99.68(8) Y N2 FE1 N8 . . . 100.88(8) Y N7 FE1 N8 . . . 79.29(8) Y N1 FE1 N8 . . . 92.07(7) Y N2 FE1 N3 . . . 79.45(8) Y N7 FE1 N3 . . . 101.17(8) Y N1 FE1 N3 . . . 159.09(8) Y N8 FE1 N3 . . . 93.32(7) Y N2 FE1 N6 . . . 100.07(8) Y N7 FE1 N6 . . . 79.76(8) Y N1 FE1 N6 . . . 91.00(7) Y N8 FE1 N6 . . . 159.04(7) Y N3 FE1 N6 . . . 91.15(8) Y C1 N1 C5 . . . 117.37(19) Y C1 N1 FE1 . . . 127.75(15) Y C5 N1 FE1 . . . 114.88(14) Y C8 N2 C6 . . . 116.68(19) Y C8 N2 FE1 . . . 121.74(15) Y C6 N2 FE1 . . . 121.55(15) Y C13 N3 C9 . . . 117.4(2) Y C13 N3 FE1 . . . 127.63(16) Y C9 N3 FE1 . . . 114.83(15) Y C6 N4 C7 . . . 115.19(19) Y C8 N5 C7 . . . 115.41(19) Y C21 N6 C25 . . . 117.2(2) Y C21 N6 FE1 . . . 128.33(16) Y C25 N6 FE1 . . . 114.50(15) Y C26 N7 C28 . . . 116.77(19) Y C26 N7 FE1 . . . 121.10(15) Y C28 N7 FE1 . . . 122.04(15) Y C33 N8 C29 . . . 117.71(19) Y C33 N8 FE1 . . . 127.17(15) Y C29 N8 FE1 . . . 115.10(14) Y C26 N9 C27 . . . 115.2(2) Y C28 N10 C27 . . . 115.1(2) Y N1 C1 C2 . . . 122.6(2) Y N1 C1 H1 . . . 118.7 ? C2 C1 H1 . . . 118.7 ? C3 C2 C1 . . . 119.5(2) Y C3 C2 H2 . . . 120.3 ? C1 C2 H2 . . . 120.3 ? C2 C3 C4 . . . 119.0(2) Y C2 C3 H3 . . . 120.5 ? C4 C3 H3 . . . 120.5 ? C5 C4 C3 . . . 118.7(2) Y C5 C4 H4 . . . 120.6 ? C3 C4 H4 . . . 120.6 ? N1 C5 C4 . . . 122.8(2) Y N1 C5 C6 . . . 112.72(19) Y C4 C5 C6 . . . 124.5(2) Y N4 C6 N2 . . . 124.0(2) Y N4 C6 C5 . . . 124.9(2) Y N2 C6 C5 . . . 111.14(19) Y N5 C7 N4 . . . 124.5(2) Y N5 C7 C14 . . . 117.7(2) Y N4 C7 C14 . . . 117.8(2) Y N5 C8 N2 . . . 124.1(2) Y N5 C8 C9 . . . 124.9(2) Y N2 C8 C9 . . . 111.01(19) Y N3 C9 C10 . . . 123.1(2) Y N3 C9 C8 . . . 112.89(19) Y C10 C9 C8 . . . 124.0(2) Y C9 C10 C11 . . . 118.6(2) Y C9 C10 H10 . . . 120.7 ? C11 C10 H10 . . . 120.7 ? C12 C11 C10 . . . 118.8(2) Y C12 C11 H11 . . . 120.6 ? C10 C11 H11 . . . 120.6 ? C13 C12 C11 . . . 119.8(2) Y C13 C12 H12 . . . 120.1 ? C11 C12 H12 . . . 120.1 ? N3 C13 C12 . . . 122.3(2) Y N3 C13 H13 . . . 118.9 ? C12 C13 H13 . . . 118.9 ? C15 C14 C19 . . . 118.2(2) Y C15 C14 C7 . . . 120.9(2) Y C19 C14 C7 . . . 120.9(2) Y C16 C15 C14 . . . 120.5(2) Y C16 C15 H15 . . . 119.8 ? C14 C15 H15 . . . 119.8 ? C15 C16 C17 . . . 121.5(3) Y C15 C16 H16 . . . 119.2 ? C17 C16 H16 . . . 119.2 ? C18 C17 C16 . . . 117.8(2) Y C18 C17 C20 . . . 120.8(3) Y C16 C17 C20 . . . 121.3(3) Y C19 C18 C17 . . . 121.4(2) Y C19 C18 H18 . . . 119.3 ? C17 C18 H18 . . . 119.3 ? C18 C19 C14 . . . 120.5(2) Y C18 C19 H19 . . . 119.7 ? C14 C19 H19 . . . 119.7 ? C17 C20 H20A . . . 109.5 ? C17 C20 H20B . . . 109.5 ? H20A C20 H20B . . . 109.5 ? C17 C20 H20C . . . 109.5 ? H20A C20 H20C . . . 109.5 ? H20B C20 H20C . . . 109.5 ? N6 C21 C22 . . . 122.1(2) Y N6 C21 H21 . . . 119 ? C22 C21 H21 . . . 119 ? C23 C22 C21 . . . 120.0(2) Y C23 C22 H22 . . . 120 ? C21 C22 H22 . . . 120 ? C22 C23 C24 . . . 119.0(2) Y C22 C23 H23 . . . 120.5 ? C24 C23 H23 . . . 120.5 ? C25 C24 C23 . . . 118.3(2) Y C25 C24 H24 . . . 120.9 ? C23 C24 H24 . . . 120.9 ? C24 C25 N6 . . . 123.5(2) Y C24 C25 C26 . . . 123.7(2) Y N6 C25 C26 . . . 112.8(2) Y N9 C26 N7 . . . 124.4(2) Y N9 C26 C25 . . . 123.8(2) Y N7 C26 C25 . . . 111.76(19) Y N10 C27 N9 . . . 124.7(2) Y N10 C27 C34 . . . 119.6(2) Y N9 C27 C34 . . . 115.7(2) Y N10 C28 N7 . . . 123.6(2) Y N10 C28 C29 . . . 125.9(2) Y N7 C28 C29 . . . 110.38(19) Y N8 C29 C30 . . . 122.5(2) Y N8 C29 C28 . . . 113.17(19) Y C30 C29 C28 . . . 124.3(2) Y C29 C30 C31 . . . 119.5(2) Y C29 C30 H30 . . . 120.3 ? C31 C30 H30 . . . 120.3 ? C30 C31 C32 . . . 118.5(2) Y C30 C31 H31 . . . 120.7 ? C32 C31 H31 . . . 120.7 ? C31 C32 C33 . . . 119.5(2) Y C31 C32 H32 . . . 120.3 ? C33 C32 H32 . . . 120.3 ? N8 C33 C32 . . . 122.4(2) Y N8 C33 H33 . . . 118.8 ? C32 C33 H33 . . . 118.8 ? C39 C34 C35 . . . 119.2(2) Y C39 C34 C27 . . . 121.3(2) Y C35 C34 C27 . . . 119.5(2) Y C36 C35 C34 . . . 120.0(2) Y C36 C35 H35 . . . 120 ? C34 C35 H35 . . . 120 ? C35 C36 C37 . . . 121.5(3) Y C35 C36 H36 . . . 119.2 ? C37 C36 H36 . . . 119.2 ? C36 C37 C38 . . . 118.0(2) Y C36 C37 C40 . . . 120.6(3) Y C38 C37 C40 . . . 121.3(3) Y C39 C38 C37 . . . 121.2(2) Y C39 C38 H38 . . . 119.4 ? C37 C38 H38 . . . 119.4 ? C38 C39 C34 . . . 119.9(2) Y C38 C39 H39 . . . 120 ? C34 C39 H39 . . . 120 ? C37 C40 H40A . . . 109.5 ? C37 C40 H40B . . . 109.5 ? H40A C40 H40B . . . 109.5 ? C37 C40 H40C . . . 109.5 ? H40A C40 H40C . . . 109.5 ? H40B C40 H40C . . . 109.5 ? F15 P1 F14 . . . 91.12(12) Y F15 P1 F11 . . . 90.93(10) Y F14 P1 F11 . . . 90.74(10) Y F15 P1 F12 . . . 90.50(12) Y F14 P1 F12 . . . 177.90(13) Y F11 P1 F12 . . . 90.56(10) Y F15 P1 F13 . . . 179.74(12) Y F14 P1 F13 . . . 88.82(12) Y F11 P1 F13 . . . 89.33(10) Y F12 P1 F13 . . . 89.55(12) Y F15 P1 F16 . . . 89.17(10) Y F14 P1 F16 . . . 89.11(9) Y F11 P1 F16 . . . 179.83(12) Y F12 P1 F16 . . . 89.57(10) Y F13 P1 F16 . . . 90.57(10) Y F26 P2 F25 . . . 90.03(12) Y F26 P2 F21 . . . 179.46(12) Y F25 P2 F21 . . . 90.14(11) Y F26 P2 F22 . . . 89.58(11) Y F25 P2 F22 . . . 92.31(12) Y F21 P2 F22 . . . 90.92(10) Y F26 P2 F23 . . . 90.98(11) Y F25 P2 F23 . . . 178.42(11) Y F21 P2 F23 . . . 88.83(11) Y F22 P2 F23 . . . 88.90(11) Y F26 P2 F24 . . . 90.16(10) Y F25 P2 F24 . . . 88.88(10) Y F21 P2 F24 . . . 89.33(9) Y F22 P2 F24 . . . 178.78(12) Y F23 P2 F24 . . . 89.91(10) Y loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion _geom_torsion_publ_flag N2 FE1 N1 C1 . . . . -179.38(19) N N7 FE1 N1 C1 . . . . 0.45(19) N N8 FE1 N1 C1 . . . . 79.94(19) N N3 FE1 N1 C1 . . . . -175.18(19) N N6 FE1 N1 C1 . . . . -79.33(19) N N2 FE1 N1 C5 . . . . 1.14(15) N N7 FE1 N1 C5 . . . . -179.03(15) N N8 FE1 N1 C5 . . . . -99.55(15) N N3 FE1 N1 C5 . . . . 5.3(3) N N6 FE1 N1 C5 . . . . 101.19(15) N N1 FE1 N2 C8 . . . . 177.60(18) N N8 FE1 N2 C8 . . . . -92.26(17) N N3 FE1 N2 C8 . . . . -0.88(17) N N6 FE1 N2 C8 . . . . 88.42(18) N N1 FE1 N2 C6 . . . . -0.19(16) N N8 FE1 N2 C6 . . . . 89.95(17) N N3 FE1 N2 C6 . . . . -178.66(18) N N6 FE1 N2 C6 . . . . -89.37(17) N N2 FE1 N3 C13 . . . . 178.1(2) N N7 FE1 N3 C13 . . . . -1.7(2) N N1 FE1 N3 C13 . . . . 173.9(2) N N8 FE1 N3 C13 . . . . -81.4(2) N N6 FE1 N3 C13 . . . . 78.1(2) N N2 FE1 N3 C9 . . . . 2.28(15) N N7 FE1 N3 C9 . . . . -177.54(15) N N1 FE1 N3 C9 . . . . -1.9(3) N N8 FE1 N3 C9 . . . . 102.73(16) N N6 FE1 N3 C9 . . . . -97.75(16) N N2 FE1 N6 C21 . . . . -1.2(2) N N7 FE1 N6 C21 . . . . 179.4(2) N N1 FE1 N6 C21 . . . . -80.9(2) N N8 FE1 N6 C21 . . . . -179.3(2) N N3 FE1 N6 C21 . . . . 78.3(2) N N2 FE1 N6 C25 . . . . 178.75(15) N N7 FE1 N6 C25 . . . . -0.61(15) N N1 FE1 N6 C25 . . . . 99.04(16) N N8 FE1 N6 C25 . . . . 0.6(3) N N3 FE1 N6 C25 . . . . -101.75(16) N N1 FE1 N7 C26 . . . . -86.71(17) N N8 FE1 N7 C26 . . . . -177.00(18) N N3 FE1 N7 C26 . . . . 91.70(17) N N6 FE1 N7 C26 . . . . 2.55(16) N N1 FE1 N7 C28 . . . . 89.82(17) N N8 FE1 N7 C28 . . . . -0.47(16) N N3 FE1 N7 C28 . . . . -91.77(17) N N6 FE1 N7 C28 . . . . 179.08(18) N N2 FE1 N8 C33 . . . . -1.2(2) N N7 FE1 N8 C33 . . . . 178.2(2) N N1 FE1 N8 C33 . . . . 78.73(19) N N3 FE1 N8 C33 . . . . -81.06(19) N N6 FE1 N8 C33 . . . . 177.0(2) N N2 FE1 N8 C29 . . . . -179.78(15) N N7 FE1 N8 C29 . . . . -0.41(15) N N1 FE1 N8 C29 . . . . -99.88(15) N N3 FE1 N8 C29 . . . . 100.33(15) N N6 FE1 N8 C29 . . . . -1.7(3) N C5 N1 C1 C2 . . . . 1.1(3) N FE1 N1 C1 C2 . . . . -178.39(16) N N1 C1 C2 C3 . . . . 0.3(3) N C1 C2 C3 C4 . . . . -0.9(4) N C2 C3 C4 C5 . . . . 0.2(4) N C1 N1 C5 C4 . . . . -1.9(3) N FE1 N1 C5 C4 . . . . 177.66(17) N C1 N1 C5 C6 . . . . 178.66(18) N FE1 N1 C5 C6 . . . . -1.8(2) N C3 C4 C5 N1 . . . . 1.3(3) N C3 C4 C5 C6 . . . . -179.3(2) N C7 N4 C6 N2 . . . . 2.4(3) N C7 N4 C6 C5 . . . . -178.8(2) N C8 N2 C6 N4 . . . . 0.3(3) N FE1 N2 C6 N4 . . . . 178.22(16) N C8 N2 C6 C5 . . . . -178.61(18) N FE1 N2 C6 C5 . . . . -0.7(2) N N1 C5 C6 N4 . . . . -177.3(2) N C4 C5 C6 N4 . . . . 3.2(4) N N1 C5 C6 N2 . . . . 1.6(3) N C4 C5 C6 N2 . . . . -177.8(2) N C8 N5 C7 N4 . . . . 1.6(3) N C8 N5 C7 C14 . . . . 180.0(2) N C6 N4 C7 N5 . . . . -3.4(3) N C6 N4 C7 C14 . . . . 178.2(2) N C7 N5 C8 N2 . . . . 1.5(3) N C7 N5 C8 C9 . . . . -178.2(2) N C6 N2 C8 N5 . . . . -2.5(3) N FE1 N2 C8 N5 . . . . 179.64(16) N C6 N2 C8 C9 . . . . 177.31(18) N FE1 N2 C8 C9 . . . . -0.6(3) N C13 N3 C9 C10 . . . . -1.4(3) N FE1 N3 C9 C10 . . . . 174.87(18) N C13 N3 C9 C8 . . . . -179.47(19) N FE1 N3 C9 C8 . . . . -3.2(2) N N5 C8 C9 N3 . . . . -177.8(2) N N2 C8 C9 N3 . . . . 2.4(3) N N5 C8 C9 C10 . . . . 4.2(4) N N2 C8 C9 C10 . . . . -175.6(2) N N3 C9 C10 C11 . . . . -0.2(4) N C8 C9 C10 C11 . . . . 177.7(2) N C9 C10 C11 C12 . . . . 1.5(4) N C10 C11 C12 C13 . . . . -1.3(4) N C9 N3 C13 C12 . . . . 1.7(3) N FE1 N3 C13 C12 . . . . -174.09(18) N C11 C12 C13 N3 . . . . -0.4(4) N N5 C7 C14 C15 . . . . 168.5(2) N N4 C7 C14 C15 . . . . -13.0(3) N N5 C7 C14 C19 . . . . -11.5(3) N N4 C7 C14 C19 . . . . 167.0(2) N C19 C14 C15 C16 . . . . -3.1(4) N C7 C14 C15 C16 . . . . 176.9(2) N C14 C15 C16 C17 . . . . 0.0(4) N C15 C16 C17 C18 . . . . 2.5(4) N C15 C16 C17 C20 . . . . -175.1(3) N C16 C17 C18 C19 . . . . -1.9(4) N C20 C17 C18 C19 . . . . 175.7(3) N C17 C18 C19 C14 . . . . -1.1(4) N C15 C14 C19 C18 . . . . 3.6(4) N C7 C14 C19 C18 . . . . -176.4(2) N C25 N6 C21 C22 . . . . -0.4(3) N FE1 N6 C21 C22 . . . . 179.54(19) N N6 C21 C22 C23 . . . . 0.9(4) N C21 C22 C23 C24 . . . . -0.7(4) N C22 C23 C24 C25 . . . . 0.1(4) N C23 C24 C25 N6 . . . . 0.4(4) N C23 C24 C25 C26 . . . . -178.6(2) N C21 N6 C25 C24 . . . . -0.2(3) N FE1 N6 C25 C24 . . . . 179.83(19) N C21 N6 C25 C26 . . . . 178.8(2) N FE1 N6 C25 C26 . . . . -1.1(2) N C27 N9 C26 N7 . . . . 1.5(3) N C27 N9 C26 C25 . . . . -179.9(2) N C28 N7 C26 N9 . . . . -1.8(3) N FE1 N7 C26 N9 . . . . 174.91(17) N C28 N7 C26 C25 . . . . 179.52(18) N FE1 N7 C26 C25 . . . . -3.8(2) N C24 C25 C26 N9 . . . . 3.3(4) N N6 C25 C26 N9 . . . . -175.7(2) N C24 C25 C26 N7 . . . . -178.0(2) N N6 C25 C26 N7 . . . . 3.0(3) N C28 N10 C27 N9 . . . . -2.5(3) N C28 N10 C27 C34 . . . . 175.64(19) N C26 N9 C27 N10 . . . . 0.7(3) N C26 N9 C27 C34 . . . . -177.47(19) N C27 N10 C28 N7 . . . . 2.2(3) N C27 N10 C28 C29 . . . . -175.6(2) N C26 N7 C28 N10 . . . . -0.2(3) N FE1 N7 C28 N10 . . . . -176.91(16) N C26 N7 C28 C29 . . . . 177.83(18) N FE1 N7 C28 C29 . . . . 1.2(2) N C33 N8 C29 C30 . . . . 0.7(3) N FE1 N8 C29 C30 . . . . 179.48(18) N C33 N8 C29 C28 . . . . -177.64(19) N FE1 N8 C29 C28 . . . . 1.1(2) N N10 C28 C29 N8 . . . . 176.6(2) N N7 C28 C29 N8 . . . . -1.4(3) N N10 C28 C29 C30 . . . . -1.7(4) N N7 C28 C29 C30 . . . . -179.7(2) N N8 C29 C30 C31 . . . . -0.6(4) N C28 C29 C30 C31 . . . . 177.6(2) N C29 C30 C31 C32 . . . . -0.1(4) N C30 C31 C32 C33 . . . . 0.5(4) N C29 N8 C33 C32 . . . . -0.3(3) N FE1 N8 C33 C32 . . . . -178.87(17) N C31 C32 C33 N8 . . . . -0.3(4) N N10 C27 C34 C39 . . . . 12.9(3) N N9 C27 C34 C39 . . . . -168.9(2) N N10 C27 C34 C35 . . . . -165.4(2) N N9 C27 C34 C35 . . . . 12.9(3) N C39 C34 C35 C36 . . . . -2.6(4) N C27 C34 C35 C36 . . . . 175.7(2) N C34 C35 C36 C37 . . . . 1.2(4) N C35 C36 C37 C38 . . . . 1.4(4) N C35 C36 C37 C40 . . . . -177.2(2) N C36 C37 C38 C39 . . . . -2.7(4) N C40 C37 C38 C39 . . . . 176.0(2) N C37 C38 C39 C34 . . . . 1.3(4) N C35 C34 C39 C38 . . . . 1.4(4) N C27 C34 C39 C38 . . . . -176.9(2) N _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 68.97 _diffrn_measured_fraction_theta_full 0.987 _refine_diff_density_max 0.406 _refine_diff_density_min -0.346 _refine_diff_density_rms 0.059 # Attachment '611630.cif' data_gh10 _database_code_depnum_ccdc_archive 'CCDC 611630' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C40 H30 Co N10, 2(F6 P)' _chemical_formula_sum 'C40 H30 Co F12 N10 P2' _chemical_formula_weight 999.61 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' Co Co 0.3494 0.9721 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting tetragonal _symmetry_space_group_name_H-M I4(1)/acd loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-y+1/4, x+3/4, z+1/4' 'y+1/4, -x+1/4, z+3/4' '-x+1/2, y, -z' 'x, -y, -z+1/2' 'y+1/4, x+3/4, -z+3/4' '-y+1/4, -x+1/4, -z+1/4' 'x+1/2, y+1/2, z+1/2' '-x+1, -y+1/2, z+1' '-y+3/4, x+5/4, z+3/4' 'y+3/4, -x+3/4, z+5/4' '-x+1, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z+1' 'y+3/4, x+5/4, -z+5/4' '-y+3/4, -x+3/4, -z+3/4' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'y-1/4, -x-3/4, -z-1/4' '-y-1/4, x-1/4, -z-3/4' 'x-1/2, -y, z' '-x, y, z-1/2' '-y-1/4, -x-3/4, z-3/4' 'y-1/4, x-1/4, z-1/4' '-x+1/2, -y+1/2, -z+1/2' 'x, y+1/2, -z' 'y+1/4, -x-1/4, -z+1/4' '-y+1/4, x+1/4, -z-1/4' 'x, -y+1/2, z+1/2' '-x+1/2, y+1/2, z' '-y+1/4, -x-1/4, z-1/4' 'y+1/4, x+1/4, z+1/4' _cell_length_a 22.1997(19) _cell_length_b 22.1997(19) _cell_length_c 16.819(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 8288.7(17) _cell_formula_units_Z 8 _cell_measurement_temperature 125(2) _cell_measurement_reflns_used 995 _cell_measurement_theta_min 2.1 _cell_measurement_theta_max 28.1 _exptl_crystal_description needle _exptl_crystal_colour Orange _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.602 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 4040 _exptl_absorpt_coefficient_mu 0.591 _exptl_absorpt_correction_type multiscan _exptl_absorpt_correction_T_min 0.8426 _exptl_absorpt_correction_T_max 0.9711 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 125(2) _diffrn_radiation_wavelength 0.71070 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Smart 1000' _diffrn_measurement_method 'omega-2teta scan' _diffrn_detector_area_resol_mean '0.7 A' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 44078 _diffrn_reflns_av_R_equivalents 0.0581 _diffrn_reflns_av_sigmaI/netI 0.0216 _diffrn_reflns_limit_h_min -29 _diffrn_reflns_limit_h_max 29 _diffrn_reflns_limit_k_min -29 _diffrn_reflns_limit_k_max 29 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 1.83 _diffrn_reflns_theta_max 28.37 _reflns_number_total 2597 _reflns_number_gt 1846 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker Smart and Saint' _computing_cell_refinement 'Bruker Smart' _computing_data_reduction 'Bruker xprep' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _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^)+(0.0522P)^2^+12.6413P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef 0.0 _refine_ls_number_reflns 2597 _refine_ls_number_parameters 152 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0610 _refine_ls_R_factor_gt 0.0354 _refine_ls_wR_factor_ref 0.1142 _refine_ls_wR_factor_gt 0.0943 _refine_ls_goodness_of_fit_ref 1.073 _refine_ls_restrained_S_all 1.073 _refine_ls_shift/su_max 0.000 _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 Co1 Co 0.0000 0.2500 0.1250 0.02234(14) Uani 1 4 d S . . P1 P 0.0000 0.5000 0.0000 0.0324(2) Uani 1 2 d S . . F1 F -0.04122(7) 0.46776(7) -0.06506(10) 0.0498(4) Uani 1 1 d . . . F2 F -0.03732(7) 0.46854(7) 0.06948(10) 0.0531(4) Uani 1 1 d . . . F3 F 0.04505(7) 0.44323(7) -0.00135(10) 0.0476(4) Uani 1 1 d . . . C1 C 0.06368(11) 0.16853(10) -0.01025(18) 0.0431(6) Uani 1 1 d . . . H1 H 0.0295 0.1429 -0.0070 0.052 Uiso 1 1 calc R . . C2 C 0.10997(13) 0.15304(11) -0.06110(18) 0.0509(7) Uani 1 1 d . . . H2 H 0.1075 0.1173 -0.0919 0.061 Uiso 1 1 calc R . . C3 C 0.15957(13) 0.18977(11) -0.06674(17) 0.0473(7) Uani 1 1 d . . . H3 H 0.1920 0.1795 -0.1009 0.057 Uiso 1 1 calc R . . C4 C 0.16148(11) 0.24203(10) -0.02174(14) 0.0350(5) Uani 1 1 d . . . H4 H 0.1949 0.2687 -0.0250 0.042 Uiso 1 1 calc R . . C5 C 0.11366(9) 0.25432(9) 0.02791(13) 0.0287(4) Uani 1 1 d . . . C6 C 0.11143(9) 0.30866(9) 0.07848(12) 0.0267(4) Uani 1 1 d . . . N1 N 0.06501(8) 0.21803(8) 0.03444(12) 0.0320(4) Uani 1 1 d . . . N2 N 0.06248(8) 0.31248(8) 0.1250 0.0267(5) Uani 1 2 d S . . N3 N 0.15457(8) 0.34947(8) 0.07596(11) 0.0286(4) Uani 1 1 d . . . C7 C 0.14709(9) 0.39709(9) 0.1250 0.0275(6) Uani 1 2 d S . . C8 C 0.19356(9) 0.44356(9) 0.1250 0.0269(6) Uani 1 2 d S . . C9 C 0.25132(10) 0.43123(10) 0.09611(14) 0.0318(5) Uani 1 1 d . . . H9 H 0.2606 0.3922 0.0765 0.038 Uiso 1 1 calc R . . C10 C 0.29493(10) 0.47548(10) 0.09593(16) 0.0369(5) Uani 1 1 d . . . H10 H 0.3339 0.4667 0.0756 0.044 Uiso 1 1 calc R . . C11 C 0.28271(10) 0.53271(10) 0.1250 0.0383(8) Uani 1 2 d S . . C12 C 0.33063(11) 0.58063(11) 0.1250 0.0683(15) Uani 1 2 d S . . H12A H 0.3120 0.6201 0.1161 0.082 Uiso 0.50 1 calc PR . . H12B H 0.3597 0.5724 0.0825 0.082 Uiso 0.50 1 calc PR . . H12C H 0.3514 0.5807 0.1764 0.082 Uiso 0.50 1 calc PR . . 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 Co1 0.02305(18) 0.02305(18) 0.0209(3) 0.000 0.000 0.0008(2) P1 0.0297(4) 0.0258(4) 0.0418(5) -0.0012(3) 0.0027(3) -0.0061(3) F1 0.0481(9) 0.0405(8) 0.0607(10) -0.0092(7) -0.0117(7) -0.0073(7) F2 0.0593(10) 0.0429(8) 0.0570(10) 0.0028(7) 0.0194(8) -0.0134(7) F3 0.0460(8) 0.0368(8) 0.0599(10) -0.0051(7) -0.0022(7) 0.0077(6) C1 0.0401(13) 0.0269(11) 0.0623(17) -0.0034(11) 0.0107(12) -0.0098(10) C2 0.0550(16) 0.0326(12) 0.0651(19) -0.0177(12) 0.0178(14) -0.0104(12) C3 0.0492(15) 0.0386(13) 0.0540(16) -0.0130(12) 0.0238(13) -0.0075(11) C4 0.0358(12) 0.0294(11) 0.0398(12) -0.0032(9) 0.0116(10) -0.0070(9) C5 0.0300(10) 0.0254(10) 0.0307(10) 0.0026(8) 0.0044(8) -0.0032(8) C6 0.0288(10) 0.0274(10) 0.0239(10) 0.0021(8) 0.0006(8) 0.0002(8) N1 0.0319(10) 0.0248(9) 0.0393(11) 0.0009(8) 0.0076(8) -0.0041(7) N2 0.0274(7) 0.0274(7) 0.0254(12) 0.0002(7) -0.0002(7) 0.0001(9) N3 0.0307(9) 0.0281(9) 0.0272(9) -0.0008(7) 0.0022(7) -0.0035(7) C7 0.0288(9) 0.0288(9) 0.0251(14) 0.0024(8) -0.0024(8) -0.0003(11) C8 0.0279(8) 0.0279(8) 0.0251(14) 0.0038(9) -0.0038(9) -0.0029(11) C9 0.0312(11) 0.0275(10) 0.0366(11) -0.0003(9) -0.0017(9) -0.0007(9) C10 0.0250(10) 0.0345(12) 0.0510(14) 0.0038(11) -0.0008(10) -0.0019(9) C11 0.0291(9) 0.0291(9) 0.057(2) 0.0058(11) -0.0058(11) -0.0031(13) C12 0.0353(12) 0.0353(12) 0.134(5) -0.0030(18) 0.0030(18) -0.0117(16) _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 Co1 N2 1.962(2) 10_454 ? Co1 N2 1.962(2) . ? Co1 N1 2.2150(19) 15_444 ? Co1 N1 2.2151(19) 8 ? Co1 N1 2.2151(19) 10_454 ? Co1 N1 2.2151(19) . ? P1 F2 1.5937(15) 17_565 ? P1 F2 1.5937(15) . ? P1 F1 1.5959(15) 17_565 ? P1 F1 1.5960(15) . ? P1 F3 1.6090(14) . ? P1 F3 1.6090(14) 17_565 ? C1 N1 1.332(3) . ? C1 C2 1.381(4) . ? C2 C3 1.373(4) . ? C3 C4 1.386(3) . ? C4 C5 1.378(3) . ? C5 N1 1.352(3) . ? C5 C6 1.477(3) . ? C6 N3 1.319(3) . ? C6 N2 1.342(2) . ? N2 C6 1.342(2) 15_444 ? N3 C7 1.351(2) . ? C7 N3 1.351(2) 15_444 ? C7 C8 1.459(4) . ? C8 C9 1.398(3) 15_444 ? C8 C9 1.398(3) . ? C9 C10 1.379(3) . ? C10 C11 1.388(3) . ? C11 C10 1.388(3) 15_444 ? C11 C12 1.504(5) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N2 Co1 N2 180.0 10_454 . ? N2 Co1 N1 103.54(5) 10_454 15_444 ? N2 Co1 N1 76.46(5) . 15_444 ? N2 Co1 N1 76.46(5) 10_454 8 ? N2 Co1 N1 103.54(5) . 8 ? N1 Co1 N1 93.12(10) 15_444 8 ? N2 Co1 N1 76.46(5) 10_454 10_454 ? N2 Co1 N1 103.54(5) . 10_454 ? N1 Co1 N1 93.16(10) 15_444 10_454 ? N1 Co1 N1 152.92(9) 8 10_454 ? N2 Co1 N1 103.54(5) 10_454 . ? N2 Co1 N1 76.46(5) . . ? N1 Co1 N1 152.92(9) 15_444 . ? N1 Co1 N1 93.16(10) 8 . ? N1 Co1 N1 93.12(10) 10_454 . ? F2 P1 F2 180.0 17_565 . ? F2 P1 F1 90.47(9) 17_565 17_565 ? F2 P1 F1 89.53(9) . 17_565 ? F2 P1 F1 89.53(9) 17_565 . ? F2 P1 F1 90.47(9) . . ? F1 P1 F1 180.0 17_565 . ? F2 P1 F3 90.56(8) 17_565 . ? F2 P1 F3 89.44(8) . . ? F1 P1 F3 90.26(8) 17_565 . ? F1 P1 F3 89.74(8) . . ? F2 P1 F3 89.44(8) 17_565 17_565 ? F2 P1 F3 90.56(8) . 17_565 ? F1 P1 F3 89.74(8) 17_565 17_565 ? F1 P1 F3 90.26(8) . 17_565 ? F3 P1 F3 180.0 . 17_565 ? N1 C1 C2 122.6(2) . . ? C3 C2 C1 119.5(2) . . ? C2 C3 C4 118.9(2) . . ? C5 C4 C3 118.2(2) . . ? N1 C5 C4 123.1(2) . . ? N1 C5 C6 114.41(18) . . ? C4 C5 C6 122.46(19) . . ? N3 C6 N2 124.3(2) . . ? N3 C6 C5 121.21(18) . . ? N2 C6 C5 114.50(18) . . ? C1 N1 C5 117.63(19) . . ? C1 N1 Co1 129.64(15) . . ? C5 N1 Co1 112.67(14) . . ? C6 N2 C6 116.3(3) . 15_444 ? C6 N2 Co1 121.87(13) . . ? C6 N2 Co1 121.87(13) 15_444 . ? C6 N3 C7 115.37(19) . . ? N3 C7 N3 124.4(3) . 15_444 ? N3 C7 C8 117.79(13) . . ? N3 C7 C8 117.80(13) 15_444 . ? C9 C8 C9 118.7(3) 15_444 . ? C9 C8 C7 120.66(13) 15_444 . ? C9 C8 C7 120.66(13) . . ? C10 C9 C8 120.3(2) . . ? C9 C10 C11 120.9(2) . . ? C10 C11 C10 118.8(3) 15_444 . ? C10 C11 C12 120.60(15) 15_444 . ? C10 C11 C12 120.60(15) . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 28.37 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.778 _refine_diff_density_min -0.511 _refine_diff_density_rms 0.064 # Attachment '611631.cif' # ======================================================== # STRUCTURAL DATA # ======================================================== data_gar120 _database_code_depnum_ccdc_archive 'CCDC 611631' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C40 H30 N10 Ni, 2(P F6)' _chemical_formula_sum 'C40 H30 F12 N10 Ni P2' _chemical_formula_weight 999.39 _chemical_compound_source 'Synthesized by the authors. See text' 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 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.2955 0.4335 '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' _symmetry_cell_setting tetragonal _symmetry_space_group_name_H-M I41/acd _symmetry_space_group_name_hall '-I 4bd 2c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-y+1/4, x+3/4, z+1/4' 'y+1/4, -x+1/4, z+3/4' '-x+1/2, y, -z' 'x, -y, -z+1/2' 'y+1/4, x+3/4, -z+3/4' '-y+1/4, -x+1/4, -z+1/4' 'x+1/2, y+1/2, z+1/2' '-x+1, -y+1/2, z+1' '-y+3/4, x+5/4, z+3/4' 'y+3/4, -x+3/4, z+5/4' '-x+1, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z+1' 'y+3/4, x+5/4, -z+5/4' '-y+3/4, -x+3/4, -z+3/4' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'y-1/4, -x-3/4, -z-1/4' '-y-1/4, x-1/4, -z-3/4' 'x-1/2, -y, z' '-x, y, z-1/2' '-y-1/4, -x-3/4, z-3/4' 'y-1/4, x-1/4, z-1/4' '-x+1/2, -y+1/2, -z+1/2' 'x, y+1/2, -z' 'y+1/4, -x-1/4, -z+1/4' '-y+1/4, x+1/4, -z-1/4' 'x, -y+1/2, z+1/2' '-x+1/2, y+1/2, z' '-y+1/4, -x-1/4, z-1/4' 'y+1/4, x+1/4, z+1/4' _cell_length_a 22.2925(3) _cell_length_b 22.2925(3) _cell_length_c 16.6862(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 8292.3(3) _cell_formula_units_Z 8 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 11294 _cell_measurement_theta_min 3.97 _cell_measurement_theta_max 68.11 _exptl_crystal_description block _exptl_crystal_colour green _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.04 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.601 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 4048 _exptl_absorpt_coefficient_mu 2.300 _exptl_absorpt_correction_Type multi-scan _exptl_absorpt_correction_T_min 0.8200 _exptl_absorpt_correction_T_max 0.9800 _exptl_absorpt_process_details 'Sadabs (Sheldrick,1996)' _exptl_special_details ; X-ray crystallographic data for I were collected from a single crystal sample, which was mounted on a loop fiber. Data were collected using a Bruker Platform diffractometer, equipped with a Bruker SMART 4K Charged-Coupled Device (CCD) Area Detector using the program SMART and a rotating anode source Cu-K\a radiation. The crystal-to-detector distance was 5.120 cm, and the data collection was carried out in 512 x 512 pixel mode, utilizing 4 x 4 pixel binning. The initial unit cell parameters were determined by a least-squares fit of the angular setting of strong reflections, collected by a 9.0 degree scan in 30 frames over four different parts of the reciprocal space (120 frames total). Upon completion of the data collection, the first 101 frames were recollected in order to improve the decay correction analysis. ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'Rotating Anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker AXS Smart 4K/Platform' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 5.5 _diffrn_standards_number 259 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0.42 _diffrn_reflns_number 76131 _diffrn_reflns_av_R_equivalents 0.033 _diffrn_reflns_av_sigmaI/netI 0.0140 _diffrn_reflns_limit_h_min -26 _diffrn_reflns_limit_h_max 26 _diffrn_reflns_limit_k_min -26 _diffrn_reflns_limit_k_max 26 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 3.97 _diffrn_reflns_theta_max 68.83 _reflns_number_total 1928 _reflns_number_gt 1523 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'SMART (Bruker, 2001)' _computing_cell_refinement 'SMART (Bruker, 2001)' _computing_data_reduction 'SAINT (Bruker, 2003)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL (Bruker, 1997)' _computing_publication_material 'UdMX (local program)' _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^)+(0.0699P)^2^+17.6478P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1928 _refine_ls_number_parameters 153 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0566 _refine_ls_R_factor_gt 0.0416 _refine_ls_wR_factor_ref 0.1365 _refine_ls_wR_factor_gt 0.1140 _refine_ls_goodness_of_fit_ref 1.094 _refine_ls_restrained_S_all 1.094 _refine_ls_shift/su_max 0.000 _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 0.0000 0.2500 0.1250 0.0296(3) Uani 1 4 d S . . N1 N 0.06311(10) 0.21872(9) 0.03659(13) 0.0335(5) Uani 1 1 d . . . N2 N 0.06307(9) 0.31307(9) 0.1250 0.0305(6) Uani 1 2 d S . . N3 N 0.15441(9) 0.34950(9) 0.07533(13) 0.0327(5) Uani 1 1 d . . . C1 C 0.06078(14) 0.16889(12) -0.00776(19) 0.0428(7) Uani 1 1 d . . . H1 H 0.0267 0.1435 -0.0030 0.051 Uiso 1 1 calc R . . C2 C 0.10599(16) 0.15274(14) -0.0603(2) 0.0550(9) Uani 1 1 d . . . H2 H 0.1026 0.1171 -0.0911 0.066 Uiso 1 1 calc R . . C3 C 0.15587(16) 0.18871(14) -0.0676(2) 0.0551(9) Uani 1 1 d . . . H3 H 0.1876 0.1779 -0.1028 0.066 Uiso 1 1 calc R . . C4 C 0.15907(14) 0.24095(12) -0.02283(18) 0.0426(7) Uani 1 1 d . . . H4 H 0.1927 0.2669 -0.0271 0.051 Uiso 1 1 calc R . . C5 C 0.11215(12) 0.25428(11) 0.02808(15) 0.0342(6) Uani 1 1 d . . . C6 C 0.11142(11) 0.30903(11) 0.07800(15) 0.0304(5) Uani 1 1 d . . . C7 C 0.14693(11) 0.39693(11) 0.1250 0.0316(8) Uani 1 2 d S . . C8 C 0.19330(11) 0.44330(11) 0.1250 0.0304(7) Uani 1 2 d S . . C9 C 0.25104(12) 0.43070(11) 0.09682(17) 0.0348(6) Uani 1 1 d . . . H9 H 0.2604 0.3917 0.0778 0.042 Uiso 1 1 calc R . . C10 C 0.29428(12) 0.47480(12) 0.09665(19) 0.0415(7) Uani 1 1 d . . . H10 H 0.3332 0.4658 0.0768 0.050 Uiso 1 1 calc R . . C11 C 0.28218(12) 0.53218(12) 0.1250 0.0429(10) Uani 1 2 d S . . C12 C 0.32997(14) 0.57997(14) 0.1250 0.0779(19) Uani 1 2 d S . . H12A H 0.3669 0.5638 0.1016 0.117 Uiso 0.50 1 calc PR . . H12B H 0.3378 0.5929 0.1802 0.117 Uiso 0.50 1 calc PR . . H12C H 0.3163 0.6143 0.0932 0.117 Uiso 0.50 1 calc PR . . P1 P 0.0000 0.0000 1.0000 0.0390(3) Uani 1 2 d S . . F11 F 0.04026(9) 0.03191(8) 0.93388(12) 0.0588(5) Uani 1 1 d . . . F12 F -0.04414(8) 0.05701(8) 1.00007(12) 0.0559(5) Uani 1 1 d . . . F13 F 0.03832(9) 0.03066(9) 1.06926(13) 0.0633(6) 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 0.0275(3) 0.0275(3) 0.0338(5) 0.000 0.000 -0.0065(3) N1 0.0363(11) 0.0295(11) 0.0348(12) -0.0011(9) 0.0036(9) -0.0046(9) N2 0.0297(9) 0.0297(9) 0.0321(16) -0.0013(9) 0.0013(9) -0.0070(12) N3 0.0323(11) 0.0327(11) 0.0331(12) -0.0019(9) 0.0031(9) -0.0084(9) C1 0.0495(16) 0.0290(13) 0.0497(17) -0.0055(12) 0.0067(13) -0.0118(12) C2 0.067(2) 0.0384(15) 0.059(2) -0.0166(14) 0.0232(17) -0.0147(15) C3 0.064(2) 0.0418(16) 0.060(2) -0.0135(15) 0.0285(17) -0.0106(15) C4 0.0471(16) 0.0349(14) 0.0457(16) -0.0054(12) 0.0145(13) -0.0092(12) C5 0.0378(14) 0.0296(12) 0.0351(14) -0.0002(10) 0.0033(11) -0.0059(10) C6 0.0318(13) 0.0306(12) 0.0289(13) 0.0005(10) -0.0001(10) -0.0050(10) C7 0.0316(11) 0.0316(11) 0.0318(19) 0.0025(10) -0.0025(10) -0.0054(14) C8 0.0303(11) 0.0303(11) 0.0307(18) 0.0024(10) -0.0024(10) -0.0064(14) C9 0.0329(13) 0.0279(12) 0.0435(15) -0.0003(11) 0.0001(11) -0.0036(10) C10 0.0266(13) 0.0385(14) 0.0595(18) 0.0014(13) -0.0015(12) -0.0043(11) C11 0.0332(12) 0.0332(12) 0.062(3) 0.0058(13) -0.0058(13) -0.0076(16) C12 0.0423(17) 0.0423(17) 0.149(6) -0.008(2) 0.008(2) -0.017(2) P1 0.0376(5) 0.0308(5) 0.0487(7) 0.0040(4) -0.0035(4) -0.0071(4) F11 0.0583(11) 0.0465(10) 0.0717(13) 0.0133(9) 0.0129(9) -0.0072(9) F12 0.0551(11) 0.0448(10) 0.0678(13) 0.0075(9) 0.0033(9) 0.0068(8) F13 0.0679(13) 0.0518(11) 0.0701(14) -0.0020(9) -0.0211(10) -0.0136(9) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag Ni1 N2 . . 1.988(3) Y Ni1 N2 . 10_454 1.988(3) Y Ni1 N1 . . 2.154(2) Y Ni1 N1 . 10_454 2.154(2) Y Ni1 N1 . 8 2.155(2) Y Ni1 N1 . 15_444 2.155(2) Y N1 C1 . . 1.336(3) Y N1 C5 . . 1.358(3) Y N2 C6 . . 1.336(3) Y N2 C6 . 15_444 1.336(3) Y N3 C6 . . 1.317(3) Y N3 C7 . . 1.354(3) Y C1 C2 . . 1.383(4) Y C1 H1 . . 0.95 ? C2 C3 . . 1.376(5) Y C2 H2 . . 0.95 ? C3 C4 . . 1.385(4) Y C3 H3 . . 0.95 ? C4 C5 . . 1.380(4) Y C4 H4 . . 0.95 ? C5 C6 . . 1.478(3) Y C7 N3 . 15_444 1.354(3) Y C7 C8 . . 1.462(5) Y C8 C9 . . 1.399(3) Y C8 C9 . 15_444 1.399(3) Y C9 C10 . . 1.377(4) Y C9 H9 . . 0.95 ? C10 C11 . . 1.390(3) Y C10 H10 . . 0.95 ? C11 C10 . 15_444 1.390(3) Y C11 C12 . . 1.507(6) Y C12 H12a . . 0.98 ? C12 H12b . . 0.98 ? C12 H12c . . 0.98 ? P1 F11 . 17_557 1.5903(18) Y P1 F11 . . 1.5903(18) Y P1 F13 . 17_557 1.5914(19) Y P1 F13 . . 1.5915(19) Y P1 F12 . 17_557 1.6072(18) Y P1 F12 . . 1.6072(18) Y loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_2 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag N2 NI1 N2 . . 10_454 180 Y N2 NI1 N1 . . . 76.54(6) Y N2 NI1 N1 10_454 . . 103.46(6) Y N2 NI1 N1 . . 10_454 103.47(6) Y N2 NI1 N1 10_454 . 10_454 76.53(6) Y N1 NI1 N1 . . 10_454 93.57(12) Y N2 NI1 N1 . . 8 103.47(6) Y N2 NI1 N1 10_454 . 8 76.53(6) Y N1 NI1 N1 . . 8 92.64(12) Y N1 NI1 N1 10_454 . 8 153.07(11) Y N2 NI1 N1 . . 15_444 76.53(6) Y N2 NI1 N1 10_454 . 15_444 103.47(6) Y N1 NI1 N1 . . 15_444 153.07(11) Y N1 NI1 N1 10_454 . 15_444 92.64(12) Y N1 NI1 N1 8 . 15_444 93.57(12) Y C1 N1 C5 . . . 117.3(2) Y C1 N1 NI1 . . . 128.56(18) Y C5 N1 NI1 . . . 114.11(17) Y C6 N2 C6 . . 15_444 117.0(3) Y C6 N2 NI1 . . . 121.52(15) Y C6 N2 NI1 15_444 . . 121.52(15) Y C6 N3 C7 . . . 115.1(2) Y N1 C1 C2 . . . 122.6(3) Y N1 C1 H1 . . . 118.7 ? C2 C1 H1 . . . 118.7 ? C3 C2 C1 . . . 119.5(3) Y C3 C2 H2 . . . 120.2 ? C1 C2 H2 . . . 120.2 ? C2 C3 C4 . . . 118.9(3) Y C2 C3 H3 . . . 120.5 ? C4 C3 H3 . . . 120.5 ? C5 C4 C3 . . . 118.3(3) Y C5 C4 H4 . . . 120.9 ? C3 C4 H4 . . . 120.9 ? N1 C5 C4 . . . 123.3(2) Y N1 C5 C6 . . . 114.5(2) Y C4 C5 C6 . . . 122.2(2) Y N3 C6 N2 . . . 124.1(2) Y N3 C6 C5 . . . 122.6(2) Y N2 C6 C5 . . . 113.3(2) Y N3 C7 N3 . . 15_444 124.6(3) Y N3 C7 C8 . . . 117.73(15) Y N3 C7 C8 15_444 . . 117.72(15) Y C9 C8 C9 . . 15_444 118.9(3) Y C9 C8 C7 . . . 120.57(16) Y C9 C8 C7 15_444 . . 120.57(16) Y C10 C9 C8 . . . 120.1(2) Y C10 C9 H9 . . . 120 ? C8 C9 H9 . . . 120 ? C9 C10 C11 . . . 121.4(3) Y C9 C10 H10 . . . 119.3 ? C11 C10 H10 . . . 119.3 ? C10 C11 C10 . . 15_444 118.2(3) Y C10 C11 C12 . . . 120.89(17) Y C10 C11 C12 15_444 . . 120.89(17) Y C11 C12 H12A . . . 109.5 ? C11 C12 H12B . . . 109.5 ? H12A C12 H12B . . . 109.5 ? C11 C12 H12C . . . 109.5 ? H12A C12 H12C . . . 109.5 ? H12B C12 H12C . . . 109.5 ? F11 P1 F11 17_557 . . 180 Y F11 P1 F13 17_557 . 17_557 90.50(11) Y F11 P1 F13 . . 17_557 89.50(11) Y F11 P1 F13 17_557 . . 89.50(11) Y F11 P1 F13 . . . 90.50(11) Y F13 P1 F13 17_557 . . 179.998(1) Y F11 P1 F12 17_557 . 17_557 89.56(10) Y F11 P1 F12 . . 17_557 90.44(10) Y F13 P1 F12 17_557 . 17_557 89.34(11) Y F13 P1 F12 . . 17_557 90.66(10) Y F11 P1 F12 17_557 . . 90.44(10) Y F11 P1 F12 . . . 89.56(10) Y F13 P1 F12 17_557 . . 90.66(10) Y F13 P1 F12 . . . 89.34(11) Y F12 P1 F12 17_557 . . 180.00(11) Y loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion _geom_torsion_publ_flag N2 NI1 N1 C1 . . . . 179.9(3) N N2 NI1 N1 C1 10_454 . . . -0.1(3) N N1 NI1 N1 C1 10_454 . . . -77.1(2) N N1 NI1 N1 C1 8 . . . 76.7(2) N N1 NI1 N1 C1 15_444 . . . 179.9(3) N N2 NI1 N1 C5 . . . . 2.25(17) N N2 NI1 N1 C5 10_454 . . . -177.75(17) N N1 NI1 N1 C5 10_454 . . . 105.3(2) N N1 NI1 N1 C5 8 . . . -101.0(2) N N1 NI1 N1 C5 15_444 . . . 2.25(17) N N1 NI1 N2 C6 . . . . -1.23(14) N N1 NI1 N2 C6 10_454 . . . -91.72(14) N N1 NI1 N2 C6 8 . . . 88.28(14) N N1 NI1 N2 C6 15_444 . . . 178.77(14) N N1 NI1 N2 C6 . . . 15_444 178.77(14) N N1 NI1 N2 C6 10_454 . . 15_444 88.28(14) N N1 NI1 N2 C6 8 . . 15_444 -91.72(14) N N1 NI1 N2 C6 15_444 . . 15_444 -1.23(14) N C5 N1 C1 C2 . . . . 0.5(4) N NI1 N1 C1 C2 . . . . -177.1(3) N N1 C1 C2 C3 . . . . 0.4(5) N C1 C2 C3 C4 . . . . -1.0(6) N C2 C3 C4 C5 . . . . 0.8(5) N C1 N1 C5 C4 . . . . -0.8(4) N NI1 N1 C5 C4 . . . . 177.2(2) N C1 N1 C5 C6 . . . . 179.2(2) N NI1 N1 C5 C6 . . . . -2.9(3) N C3 C4 C5 N1 . . . . 0.1(5) N C3 C4 C5 C6 . . . . -179.8(3) N C7 N3 C6 N2 . . . . 0.5(3) N C7 N3 C6 C5 . . . . -179.9(2) N C6 N2 C6 N3 15_444 . . . -0.26(18) N NI1 N2 C6 N3 . . . . 179.74(18) N C6 N2 C6 C5 15_444 . . . -179.9(2) N NI1 N2 C6 C5 . . . . 0.1(2) N N1 C5 C6 N3 . . . . -177.7(2) N C4 C5 C6 N3 . . . . 2.2(4) N N1 C5 C6 N2 . . . . 2.0(3) N C4 C5 C6 N2 . . . . -178.1(2) N C6 N3 C7 N3 . . . 15_444 -0.22(16) N C6 N3 C7 C8 . . . . 179.78(16) N N3 C7 C8 C9 . . . . -20.78(17) N N3 C7 C8 C9 15_444 . . . 159.22(17) N N3 C7 C8 C9 . . . 15_444 159.22(17) N N3 C7 C8 C9 15_444 . . 15_444 -20.78(17) N C9 C8 C9 C10 15_444 . . . -0.4(2) N C7 C8 C9 C10 . . . . 179.6(2) N C8 C9 C10 C11 . . . . 0.8(4) N C9 C10 C11 C10 . . . 15_444 -0.4(2) N C9 C10 C11 C12 . . . . 179.6(2) N _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 68.83 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.275 _refine_diff_density_min -0.472 _refine_diff_density_rms 0.059 # Attachment '611632.cif' # ======================================================== # STRUCTURAL DATA # ======================================================== data_gar115 _database_code_depnum_ccdc_archive 'CCDC 611632' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C40 H30 Cu N10, 2(F6 P)' _chemical_formula_sum 'C40 H30 Cu F12 N10 P2' _chemical_formula_weight 1004.22 _chemical_compound_source 'Synthesized by the authors. See text' 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 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu -1.9646 0.5888 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting tetragonal _symmetry_space_group_name_H-M I41/acd _symmetry_space_group_name_hall '-I 4bd 2c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-y+1/4, x+3/4, z+1/4' 'y+1/4, -x+1/4, z+3/4' '-x+1/2, y, -z' 'x, -y, -z+1/2' 'y+1/4, x+3/4, -z+3/4' '-y+1/4, -x+1/4, -z+1/4' 'x+1/2, y+1/2, z+1/2' '-x+1, -y+1/2, z+1' '-y+3/4, x+5/4, z+3/4' 'y+3/4, -x+3/4, z+5/4' '-x+1, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z+1' 'y+3/4, x+5/4, -z+5/4' '-y+3/4, -x+3/4, -z+3/4' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'y-1/4, -x-3/4, -z-1/4' '-y-1/4, x-1/4, -z-3/4' 'x-1/2, -y, z' '-x, y, z-1/2' '-y-1/4, -x-3/4, z-3/4' 'y-1/4, x-1/4, z-1/4' '-x+1/2, -y+1/2, -z+1/2' 'x, y+1/2, -z' 'y+1/4, -x-1/4, -z+1/4' '-y+1/4, x+1/4, -z-1/4' 'x, -y+1/2, z+1/2' '-x+1/2, y+1/2, z' '-y+1/4, -x-1/4, z-1/4' 'y+1/4, x+1/4, z+1/4' _cell_length_a 22.598(4) _cell_length_b 22.598(4) _cell_length_c 17.155(7) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 8761(4) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 9521 _cell_measurement_theta_min 3.73 _cell_measurement_theta_max 46.64 _exptl_crystal_description block _exptl_crystal_colour green _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.523 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 4056 _exptl_absorpt_coefficient_mu 2.242 _exptl_absorpt_correction_Type multi-scan _exptl_absorpt_correction_T_min 0.9200 _exptl_absorpt_correction_T_max 0.9200 _exptl_absorpt_process_details 'Sadabs (Sheldrick,1996)' _exptl_special_details ; X-ray crystallographic data for I were collected from a single crystal sample, which was mounted on a loop fiber. Data were collected using a Bruker Platform diffractometer, equipped with a Bruker SMART 4K Charged-Coupled Device (CCD) Area Detector using the program SMART and a rotating anode source Cu-K\a radiation. The crystal-to-detector distance was 5.120 cm, and the data collection was carried out in 512 x 512 pixel mode, utilizing 4 x 4 pixel binning. The initial unit cell parameters were determined by a least-squares fit of the angular setting of strong reflections, collected by a 9.0 degree scan in 30 frames over four different parts of the reciprocal space (120 frames total). Upon completion of the data collection, the first 101 frames were recollected in order to improve the decay correction analysis. ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'Rotating Anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker AXS Smart 4K/Platform' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 5.5 _diffrn_standards_number 104 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 2.99 _diffrn_reflns_number 37122 _diffrn_reflns_av_R_equivalents 0.067 _diffrn_reflns_av_sigmaI/netI 0.0238 _diffrn_reflns_limit_h_min -24 _diffrn_reflns_limit_h_max 23 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 3.91 _diffrn_reflns_theta_max 57.24 _reflns_number_total 1494 _reflns_number_gt 1183 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'SMART (Bruker, 2001)' _computing_cell_refinement 'SMART (Bruker, 2001)' _computing_data_reduction 'SAINT (Bruker, 2003)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL (Bruker, 1997)' _computing_publication_material 'UdMX (local program)' _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^)+(0.0553P)^2^+10.0573P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1494 _refine_ls_number_parameters 153 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0428 _refine_ls_R_factor_gt 0.0296 _refine_ls_wR_factor_ref 0.0955 _refine_ls_wR_factor_gt 0.0797 _refine_ls_goodness_of_fit_ref 1.022 _refine_ls_restrained_S_all 1.022 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu 0.0000 0.2500 0.1250 0.0375(3) Uani 1 4 d S . . N1 N 0.06511(10) 0.21805(9) 0.03423(13) 0.0409(6) Uani 1 1 d . . . N2 N 0.06265(9) 0.31265(9) 0.1250 0.0357(7) Uani 1 2 d S . . N3 N 0.15476(9) 0.34952(9) 0.07595(12) 0.0369(5) Uani 1 1 d . . . C1 C 0.06356(13) 0.16856(12) -0.0107(2) 0.0518(8) Uani 1 1 d . . . H1 H 0.0298 0.1436 -0.0080 0.062 Uiso 1 1 calc R . . C2 C 0.11015(13) 0.15301(13) -0.0612(2) 0.0580(8) Uani 1 1 d . . . H2 H 0.1079 0.1178 -0.0913 0.070 Uiso 1 1 calc R . . C3 C 0.15983(14) 0.18975(12) -0.06691(18) 0.0537(8) Uani 1 1 d . . . H3 H 0.1917 0.1797 -0.1006 0.064 Uiso 1 1 calc R . . C4 C 0.16174(12) 0.24190(11) -0.02177(16) 0.0417(7) Uani 1 1 d . . . H4 H 0.1947 0.2680 -0.0248 0.050 Uiso 1 1 calc R . . C5 C 0.11397(11) 0.25444(11) 0.02778(15) 0.0362(6) Uani 1 1 d . . . C6 C 0.11157(11) 0.30867(11) 0.07835(14) 0.0347(6) Uani 1 1 d . . . C7 C 0.14745(11) 0.39745(11) 0.1250 0.0344(8) Uani 1 2 d S . . C8 C 0.19390(11) 0.44390(11) 0.1250 0.0348(8) Uani 1 2 d S . . C9 C 0.25170(11) 0.43160(11) 0.09597(16) 0.0394(6) Uani 1 1 d . . . H9 H 0.2608 0.3933 0.0767 0.047 Uiso 1 1 calc R . . C10 C 0.29524(11) 0.47572(11) 0.09574(18) 0.0442(7) Uani 1 1 d . . . H10 H 0.3335 0.4671 0.0757 0.053 Uiso 1 1 calc R . . C11 C 0.28308(12) 0.53308(12) 0.1250 0.0469(10) Uani 1 2 d S . . C12 C 0.33119(13) 0.58119(13) 0.1250 0.0756(16) Uani 1 2 d S . . H12A H 0.3697 0.5632 0.1136 0.113 Uiso 0.50 1 calc PR . . H12B H 0.3326 0.6002 0.1763 0.113 Uiso 0.50 1 calc PR . . H12C H 0.3220 0.6108 0.0851 0.113 Uiso 0.50 1 calc PR . . P2 P 0.5000 0.0000 1.0000 0.0393(3) Uani 1 2 d S . . F11 F 0.54505(7) 0.05682(7) 1.00145(10) 0.0527(5) Uani 1 1 d . . . F12 F 0.46250(7) 0.03131(7) 0.93053(10) 0.0584(5) Uani 1 1 d . . . F13 F 0.45860(7) 0.03211(7) 1.06497(10) 0.0543(5) 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 Cu1 0.0366(3) 0.0366(3) 0.0394(5) 0.000 0.000 0.0009(3) N1 0.0400(13) 0.0292(12) 0.0535(14) 0.0017(10) 0.0055(11) -0.0034(9) N2 0.0355(10) 0.0355(10) 0.0361(17) -0.0004(10) 0.0004(10) -0.0003(13) N3 0.0373(12) 0.0338(12) 0.0395(13) -0.0001(10) 0.0032(9) -0.0032(10) C1 0.0446(17) 0.0311(15) 0.080(2) -0.0023(14) 0.0097(15) -0.0094(13) C2 0.0585(19) 0.0383(16) 0.077(2) -0.0170(15) 0.0160(16) -0.0096(15) C3 0.0547(19) 0.0423(17) 0.064(2) -0.0098(14) 0.0217(15) -0.0060(14) C4 0.0404(16) 0.0347(15) 0.0500(17) -0.0026(12) 0.0105(13) -0.0096(12) C5 0.0388(15) 0.0303(13) 0.0396(15) 0.0023(11) 0.0036(12) -0.0026(11) C6 0.0369(15) 0.0339(14) 0.0333(14) 0.0014(11) 0.0001(11) -0.0002(12) C7 0.0343(12) 0.0343(12) 0.035(2) 0.0037(11) -0.0037(11) 0.0010(15) C8 0.0339(12) 0.0339(12) 0.036(2) 0.0032(11) -0.0032(11) -0.0002(15) C9 0.0395(15) 0.0331(14) 0.0458(15) 0.0006(12) -0.0037(12) 0.0014(11) C10 0.0303(14) 0.0390(16) 0.0633(18) 0.0038(13) -0.0031(13) 0.0001(12) C11 0.0373(13) 0.0373(13) 0.066(3) 0.0088(14) -0.0088(14) -0.0020(17) C12 0.0410(16) 0.0410(16) 0.145(5) -0.002(2) 0.002(2) -0.006(2) P2 0.0336(5) 0.0311(5) 0.0532(7) 0.0000(4) -0.0036(4) 0.0057(4) F11 0.0473(9) 0.0411(9) 0.0695(11) -0.0030(8) 0.0010(8) -0.0053(7) F12 0.0611(11) 0.0459(10) 0.0683(12) 0.0020(8) -0.0186(8) 0.0123(8) F13 0.0488(9) 0.0436(9) 0.0706(11) -0.0068(8) 0.0086(8) 0.0054(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag Cu1 N2 . 10_454 2.002(3) Y Cu1 N2 . . 2.002(3) Y Cu1 N1 . 15_444 2.261(2) Y Cu1 N1 . 8 2.261(2) Y Cu1 N1 . . 2.261(2) Y Cu1 N1 . 10_454 2.261(2) Y N1 C1 . . 1.359(4) Y N1 C5 . . 1.381(3) Y N2 C6 . 15_444 1.368(3) Y N2 C6 . . 1.368(3) Y N3 C6 . . 1.344(3) Y N3 C7 . . 1.381(3) Y C1 C2 . . 1.408(4) Y C1 H1 . . 0.95 ? C2 C3 . . 1.400(4) Y C2 H2 . . 0.95 ? C3 C4 . . 1.411(4) Y C3 H3 . . 0.95 ? C4 C5 . . 1.403(4) Y C4 H4 . . 0.95 ? C5 C6 . . 1.503(4) Y C7 N3 . 15_444 1.381(3) Y C7 C8 . . 1.485(5) Y C8 C9 . 15_444 1.425(3) Y C8 C9 . . 1.425(3) Y C9 C10 . . 1.401(4) Y C9 H9 . . 0.95 ? C10 C11 . . 1.417(3) Y C10 H10 . . 0.95 ? C11 C10 . 15_444 1.417(3) Y C11 C12 . . 1.538(6) Y C12 H12a . . 0.98 ? C12 H12b . . 0.98 ? C12 H12c . . 0.98 ? P2 F12 . 17_657 1.6244(16) Y P2 F12 . . 1.6245(16) Y P2 F13 . . 1.6261(16) Y P2 F13 . 17_657 1.6261(16) Y P2 F11 . 17_657 1.6387(16) Y P2 F11 . . 1.6387(16) Y loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_2 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag N2 CU1 N2 10_454 . . 180.00(17) Y N2 CU1 N1 10_454 . 15_444 103.56(5) Y N2 CU1 N1 . . 15_444 76.45(5) Y N2 CU1 N1 10_454 . 8 76.45(5) Y N2 CU1 N1 . . 8 103.55(5) Y N1 CU1 N1 15_444 . 8 92.94(12) Y N2 CU1 N1 10_454 . . 103.55(5) Y N2 CU1 N1 . . . 76.45(5) Y N1 CU1 N1 15_444 . . 152.89(11) Y N1 CU1 N1 8 . . 93.36(11) Y N2 CU1 N1 10_454 . 10_454 76.45(5) Y N2 CU1 N1 . . 10_454 103.55(5) Y N1 CU1 N1 15_444 . 10_454 93.36(11) Y N1 CU1 N1 8 . 10_454 152.89(11) Y N1 CU1 N1 . . 10_454 92.93(12) Y C1 N1 C5 . . . 117.7(2) Y C1 N1 CU1 . . . 129.58(17) Y C5 N1 CU1 . . . 112.66(16) Y C6 N2 C6 15_444 . . 116.6(3) Y C6 N2 CU1 15_444 . . 121.67(15) Y C6 N2 CU1 . . . 121.68(15) Y C6 N3 C7 . . . 115.6(2) Y N1 C1 C2 . . . 122.4(2) Y N1 C1 H1 . . . 118.8 ? C2 C1 H1 . . . 118.8 ? C3 C2 C1 . . . 119.6(3) Y C3 C2 H2 . . . 120.2 ? C1 C2 H2 . . . 120.2 ? C2 C3 C4 . . . 118.8(3) Y C2 C3 H3 . . . 120.6 ? C4 C3 H3 . . . 120.6 ? C5 C4 C3 . . . 118.5(2) Y C5 C4 H4 . . . 120.7 ? C3 C4 H4 . . . 120.7 ? N1 C5 C4 . . . 122.9(2) Y N1 C5 C6 . . . 114.2(2) Y C4 C5 C6 . . . 122.8(2) Y N3 C6 N2 . . . 124.1(2) Y N3 C6 C5 . . . 121.1(2) Y N2 C6 C5 . . . 114.9(2) Y N3 C7 N3 15_444 . . 124.0(3) Y N3 C7 C8 15_444 . . 118.02(15) Y N3 C7 C8 . . . 118.02(15) Y C9 C8 C9 15_444 . . 118.7(3) Y C9 C8 C7 15_444 . . 120.67(16) Y C9 C8 C7 . . . 120.67(16) Y C10 C9 C8 . . . 120.4(3) Y C10 C9 H9 . . . 119.8 ? C8 C9 H9 . . . 119.8 ? C9 C10 C11 . . . 120.9(3) Y C9 C10 H10 . . . 119.5 ? C11 C10 H10 . . . 119.5 ? C10 C11 C10 15_444 . . 118.7(3) Y C10 C11 C12 15_444 . . 120.64(17) Y C10 C11 C12 . . . 120.65(17) Y C11 C12 H12A . . . 109.5 ? C11 C12 H12B . . . 109.5 ? H12A C12 H12B . . . 109.5 ? C11 C12 H12C . . . 109.5 ? H12A C12 H12C . . . 109.5 ? H12B C12 H12C . . . 109.5 ? F12 P2 F12 17_657 . . 180.0(1) Y F12 P2 F13 17_657 . . 89.52(9) Y F12 P2 F13 . . . 90.47(9) Y F12 P2 F13 17_657 . 17_657 90.48(9) Y F12 P2 F13 . . 17_657 89.53(9) Y F13 P2 F13 . . 17_657 180.000(1) Y F12 P2 F11 17_657 . 17_657 89.66(8) Y F12 P2 F11 . . 17_657 90.34(8) Y F13 P2 F11 . . 17_657 90.15(8) Y F13 P2 F11 17_657 . 17_657 89.85(8) Y F12 P2 F11 17_657 . . 90.34(8) Y F12 P2 F11 . . . 89.66(8) Y F13 P2 F11 . . . 89.85(8) Y F13 P2 F11 17_657 . . 90.15(8) Y F11 P2 F11 17_657 . . 180 Y loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion _geom_torsion_publ_flag N2 CU1 N1 C1 10_454 . . . 0.1(3) n N2 CU1 N1 C1 . . . . -179.9(3) n N1 CU1 N1 C1 15_444 . . . -179.9(3) n N1 CU1 N1 C1 8 . . . 77.0(2) n N1 CU1 N1 C1 10_454 . . . -76.7(2) n N2 CU1 N1 C5 10_454 . . . -177.17(16) n N2 CU1 N1 C5 . . . . 2.84(16) n N1 CU1 N1 C5 15_444 . . . 2.84(16) n N1 CU1 N1 C5 8 . . . -100.30(19) n N1 CU1 N1 C5 10_454 . . . 106.08(18) n N1 CU1 N2 C6 15_444 . . 15_444 -1.68(13) n N1 CU1 N2 C6 8 . . 15_444 -91.46(13) n N1 CU1 N2 C6 . . . 15_444 178.32(13) n N1 CU1 N2 C6 10_454 . . 15_444 88.54(13) n N1 CU1 N2 C6 15_444 . . . 178.32(13) n N1 CU1 N2 C6 8 . . . 88.55(13) n N1 CU1 N2 C6 . . . . -1.68(13) n N1 CU1 N2 C6 10_454 . . . -91.45(13) n C5 N1 C1 C2 . . . . 1.6(4) n CU1 N1 C1 C2 . . . . -175.6(2) n N1 C1 C2 C3 . . . . -0.9(5) n C1 C2 C3 C4 . . . . -0.3(5) n C2 C3 C4 C5 . . . . 0.8(4) n C1 N1 C5 C4 . . . . -1.1(4) n CU1 N1 C5 C4 . . . . 176.6(2) n C1 N1 C5 C6 . . . . 178.9(2) n CU1 N1 C5 C6 . . . . -3.5(3) n C3 C4 C5 N1 . . . . -0.1(4) n C3 C4 C5 C6 . . . . 179.9(3) n C7 N3 C6 N2 . . . . 0.4(3) n C7 N3 C6 C5 . . . . 179.82(19) n C6 N2 C6 N3 15_444 . . . -0.21(17) n CU1 N2 C6 N3 . . . . 179.79(17) n C6 N2 C6 C5 15_444 . . . -179.7(2) n CU1 N2 C6 C5 . . . . 0.3(2) n N1 C5 C6 N3 . . . . -177.2(2) n C4 C5 C6 N3 . . . . 2.8(4) n N1 C5 C6 N2 . . . . 2.3(3) n C4 C5 C6 N2 . . . . -177.7(2) n C6 N3 C7 N3 . . . 15_444 -0.19(14) n C6 N3 C7 C8 . . . . 179.82(14) n N3 C7 C8 C9 15_444 . . 15_444 -19.66(16) n N3 C7 C8 C9 . . . 15_444 160.34(16) n N3 C7 C8 C9 15_444 . . . 160.34(16) n N3 C7 C8 C9 . . . . -19.66(16) n C9 C8 C9 C10 15_444 . . . -0.35(19) n C7 C8 C9 C10 . . . . 179.65(19) n C8 C9 C10 C11 . . . . 0.7(4) n C9 C10 C11 C10 . . . 15_444 -0.35(19) n C9 C10 C11 C12 . . . . 179.65(19) n _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 57.24 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.265 _refine_diff_density_min -0.275 _refine_diff_density_rms 0.043 # Attachment '611633.cif' data_gary94 _database_code_depnum_ccdc_archive 'CCDC 611633' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C19 H12 Br N5, 2(H2 O)' _chemical_formula_sum 'C19 H16 Br N5 O2' _chemical_formula_weight 426.28 _chemical_compound_source 'Synthesized by the authors. See text' 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 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.6763 1.2805 '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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21/c _symmetry_space_group_name_hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 24.9536(10) _cell_length_b 3.9351(2) _cell_length_c 19.0793(8) _cell_angle_alpha 90.00 _cell_angle_beta 110.007(2) _cell_angle_gamma 90.00 _cell_volume 1760.43(14) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 9181 _cell_measurement_theta_min 3.77 _cell_measurement_theta_max 68.24 _exptl_crystal_description block _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.04 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.608 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 864 _exptl_absorpt_coefficient_mu 3.406 _exptl_absorpt_correction_Type multi-scan _exptl_absorpt_correction_T_min 0.6300 _exptl_absorpt_correction_T_max 0.9500 _exptl_absorpt_process_details 'Sadabs (Sheldrick,1996)' _exptl_special_details ; X-ray crystallographic data for I were collected from a single crystal sample, which was mounted on a loop fiber. Data were collected using a Bruker Platform diffractometer, equipped with a Bruker SMART 4K Charged-Coupled Device (CCD) Area Detector using the program SMART and a rotating anode source Cu-K\a radiation. The crystal-to-detector distance was 5.120 cm, and the data collection was carried out in 512 x 512 pixel mode, utilizing 4 x 4 pixel binning. The initial unit cell parameters were determined by a least-squares fit of the angular setting of strong reflections, collected by a 9.0 degree scan in 30 frames over four different parts of the reciprocal space (120 frames total). Upon completion of the data collection, the first 101 frames were recollected in order to improve the decay correction analysis. ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'Rotating Anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker AXS Smart 4K/Platform' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 5.5 _diffrn_standards_number 99 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0.35 _diffrn_reflns_number 23442 _diffrn_reflns_av_R_equivalents 0.046 _diffrn_reflns_av_sigmaI/netI 0.0291 _diffrn_reflns_limit_h_min -29 _diffrn_reflns_limit_h_max 29 _diffrn_reflns_limit_k_min -4 _diffrn_reflns_limit_k_max 4 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 1.88 _diffrn_reflns_theta_max 68.58 _reflns_number_total 3232 _reflns_number_gt 2607 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'SMART (Bruker, 2001)' _computing_cell_refinement 'SMART (Bruker, 2001)' _computing_data_reduction 'SAINT (Bruker, 2003)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL (Bruker, 1997)' _computing_publication_material 'UdMX (local program)' _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^)+(0.0787P)^2^+1.3158P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3232 _refine_ls_number_parameters 256 _refine_ls_number_restraints 6 _refine_ls_R_factor_all 0.0556 _refine_ls_R_factor_gt 0.0440 _refine_ls_wR_factor_ref 0.1215 _refine_ls_wR_factor_gt 0.1135 _refine_ls_goodness_of_fit_ref 1.048 _refine_ls_restrained_S_all 1.047 _refine_ls_shift/su_max 0.000 _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 N1 N 0.89361(14) 0.7800(11) 0.2187(2) 0.0549(9) Uani 1 1 d . . . N2 N 0.79254(12) 0.9630(8) 0.11201(16) 0.0315(6) Uani 1 1 d . . . N3 N 0.79350(13) 1.3064(8) -0.01211(17) 0.0360(7) Uani 1 1 d . . . N4 N 0.74047(11) 0.6936(8) 0.18034(15) 0.0304(6) Uani 1 1 d . . . N5 N 0.69124(11) 0.9631(8) 0.06502(15) 0.0283(6) Uani 1 1 d . . . C1 C 0.94349(17) 0.6999(13) 0.2754(3) 0.0571(12) Uani 1 1 d . . . H1 H 0.9788 0.7601 0.2700 0.069 Uiso 1 1 calc R . . C2 C 0.94426(18) 0.5389(12) 0.3384(3) 0.0540(11) Uani 1 1 d . . . H2 H 0.9793 0.4821 0.3762 0.065 Uiso 1 1 calc R . . C3 C 0.89226(19) 0.4590(13) 0.3462(3) 0.0530(11) Uani 1 1 d . . . H3 H 0.8918 0.3480 0.3902 0.064 Uiso 1 1 calc R . . C4 C 0.84243(15) 0.5368(11) 0.2921(2) 0.0382(8) Uani 1 1 d . . . H4 H 0.8071 0.4809 0.2977 0.046 Uiso 1 1 calc R . . C5 C 0.84387(14) 0.6962(10) 0.2298(2) 0.0339(8) Uani 1 1 d . . . C6 C 0.78916(14) 0.7887(9) 0.17070(18) 0.0295(7) Uani 1 1 d . . . C7 C 0.69277(14) 0.7887(8) 0.12544(17) 0.0269(7) Uani 1 1 d . . . C8 C 0.74173(14) 1.0419(9) 0.06007(18) 0.0288(7) Uani 1 1 d . . . C9 C 0.74220(14) 1.2283(9) -0.00744(18) 0.0290(7) Uani 1 1 d . . . C10 C 0.69152(14) 1.3165(9) -0.06201(18) 0.0306(7) Uani 1 1 d . . . H10 H 0.6561 1.2634 -0.0563 0.037 Uiso 1 1 calc R . . C11 C 0.69306(16) 1.4828(11) -0.1249(2) 0.0369(8) Uani 1 1 d . . . H11 H 0.6586 1.5444 -0.1632 0.044 Uiso 1 1 calc R . . C12 C 0.74521(16) 1.5593(10) -0.1318(2) 0.0369(8) Uani 1 1 d . . . H12 H 0.7474 1.6695 -0.1751 0.044 Uiso 1 1 calc R . . C13 C 0.79429(16) 1.4694(11) -0.0733(2) 0.0389(8) Uani 1 1 d . . . H13 H 0.8302 1.5268 -0.0769 0.047 Uiso 1 1 calc R . . C14 C 0.63741(13) 0.6945(8) 0.13276(17) 0.0258(7) Uani 1 1 d . . . C15 C 0.63504(14) 0.5189(9) 0.19533(18) 0.0290(7) Uani 1 1 d . . . H15 H 0.6695 0.4582 0.2338 0.035 Uiso 1 1 calc R . . C16 C 0.58328(15) 0.4322(9) 0.20203(19) 0.0301(7) Uani 1 1 d . . . H16 H 0.5818 0.3147 0.2448 0.036 Uiso 1 1 calc R . . C17 C 0.53330(14) 0.5209(9) 0.14463(18) 0.0264(7) Uani 1 1 d . . . C18 C 0.53448(13) 0.6953(9) 0.08241(18) 0.0290(7) Uani 1 1 d . . . H18 H 0.4999 0.7547 0.0440 0.035 Uiso 1 1 calc R . . C19 C 0.58649(14) 0.7826(9) 0.07659(18) 0.0288(7) Uani 1 1 d . . . H19 H 0.5876 0.9035 0.0340 0.035 Uiso 1 1 calc R . . Br1 Br 0.461907(14) 0.38036(10) 0.14965(2) 0.03399(16) Uani 1 1 d . . . O12 O 0.90677(13) 1.0598(11) 0.0738(3) 0.134(2) Uani 1 1 d D . . H12A H 0.8715(7) 1.09(2) 0.061(5) 0.160 Uiso 1 1 d D . . H12B H 0.918(3) 0.893(16) 0.103(4) 0.160 Uiso 1 1 d D . . O11 O 0.94878(17) 1.5423(9) 0.0125(3) 0.1179(19) Uani 1 1 d D . . H11A H 0.948(4) 1.364(10) 0.037(4) 0.141 Uiso 1 1 d D . . H11B H 0.932(3) 1.705(11) 0.025(4) 0.141 Uiso 1 1 d 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 N1 0.0339(17) 0.071(3) 0.063(2) 0.006(2) 0.0209(16) 0.0038(18) N2 0.0294(14) 0.0354(17) 0.0330(15) -0.0011(13) 0.0147(12) 0.0000(13) N3 0.0339(15) 0.0418(19) 0.0378(16) 0.0001(14) 0.0192(13) 0.0006(14) N4 0.0256(14) 0.0340(17) 0.0327(14) -0.0004(12) 0.0113(11) -0.0003(12) N5 0.0276(14) 0.0317(16) 0.0291(14) -0.0005(12) 0.0141(11) -0.0002(12) C1 0.0282(19) 0.069(3) 0.075(3) 0.005(3) 0.019(2) 0.000(2) C2 0.034(2) 0.057(3) 0.059(3) 0.009(2) 0.0013(18) 0.007(2) C3 0.048(2) 0.058(3) 0.048(2) 0.011(2) 0.0114(19) -0.005(2) C4 0.0296(17) 0.047(2) 0.0369(18) 0.0069(17) 0.0103(15) -0.0038(17) C5 0.0260(16) 0.037(2) 0.0391(18) -0.0012(16) 0.0120(14) 0.0021(15) C6 0.0286(16) 0.0293(18) 0.0332(17) -0.0019(14) 0.0138(14) 0.0005(14) C7 0.0313(16) 0.0246(17) 0.0290(16) -0.0045(13) 0.0158(13) 0.0006(14) C8 0.0301(16) 0.0284(18) 0.0299(16) -0.0037(14) 0.0128(14) 0.0006(14) C9 0.0312(16) 0.0277(17) 0.0318(16) -0.0060(14) 0.0156(14) -0.0035(14) C10 0.0291(16) 0.037(2) 0.0301(16) -0.0018(15) 0.0151(14) -0.0021(15) C11 0.0391(19) 0.041(2) 0.0328(18) -0.0008(16) 0.0152(16) -0.0012(17) C12 0.045(2) 0.039(2) 0.0322(17) 0.0003(16) 0.0208(16) -0.0003(17) C13 0.0371(19) 0.048(2) 0.0413(19) -0.0002(17) 0.0254(16) -0.0018(18) C14 0.0275(16) 0.0256(18) 0.0267(15) -0.0051(13) 0.0125(13) -0.0026(13) C15 0.0292(16) 0.0299(18) 0.0290(16) 0.0000(14) 0.0115(14) 0.0017(14) C16 0.0335(17) 0.0287(19) 0.0309(16) 0.0038(14) 0.0149(14) -0.0005(14) C17 0.0281(15) 0.0222(16) 0.0322(16) -0.0043(13) 0.0148(13) -0.0028(13) C18 0.0255(16) 0.0305(19) 0.0308(16) -0.0011(14) 0.0093(13) 0.0019(14) C19 0.0323(17) 0.0320(19) 0.0247(15) 0.0007(14) 0.0130(13) 0.0014(15) Br1 0.0296(2) 0.0334(2) 0.0443(2) -0.00130(16) 0.01956(16) -0.00270(15) O12 0.055(2) 0.236(8) 0.099(4) 0.018(4) 0.012(2) 0.013(4) O11 0.069(3) 0.200(6) 0.086(3) 0.002(4) 0.027(2) 0.005(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag N1 C5 . . 1.369(5) Y N1 C1 . . 1.377(6) Y N2 C6 . . 1.340(5) Y N2 C8 . . 1.351(4) Y N3 C13 . . 1.337(5) Y N3 C9 . . 1.349(4) Y N4 C7 . . 1.342(4) Y N4 C6 . . 1.343(4) Y N5 C7 . . 1.331(4) Y N5 C8 . . 1.332(4) Y C1 C2 . . 1.354(7) Y C1 H1 . . 0.95 ? C2 C3 . . 1.391(6) Y C2 H2 . . 0.95 ? C3 C4 . . 1.351(6) Y C3 H3 . . 0.95 ? C4 C5 . . 1.356(5) Y C4 H4 . . 0.95 ? C5 C6 . . 1.488(5) Y C7 C14 . . 1.482(4) Y C8 C9 . . 1.486(5) Y C9 C10 . . 1.379(5) Y C10 C11 . . 1.379(5) Y C10 H10 . . 0.95 ? C11 C12 . . 1.385(5) Y C11 H11 . . 0.95 ? C12 C13 . . 1.392(5) Y C12 H12 . . 0.95 ? C13 H13 . . 0.95 ? C14 C19 . . 1.397(5) Y C14 C15 . . 1.398(5) Y C15 C16 . . 1.383(5) Y C15 H15 . . 0.95 ? C16 C17 . . 1.394(5) Y C16 H16 . . 0.95 ? C17 C18 . . 1.380(5) Y C17 Br1 . . 1.899(3) Y C18 C19 . . 1.383(5) Y C18 H18 . . 0.95 ? C19 H19 . . 0.95 ? O12 H12a . . 0.84(3) ? O12 H12b . . 0.84(7) ? O11 H11a . . 0.84(5) ? O11 H11b . . 0.84(6) ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_2 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C5 N1 C1 . . . 116.6(4) Y C6 N2 C8 . . . 114.8(3) Y C13 N3 C9 . . . 117.7(3) Y C7 N4 C6 . . . 114.7(3) Y C7 N5 C8 . . . 115.7(3) Y C2 C1 N1 . . . 122.6(4) Y C2 C1 H1 . . . 118.7 ? N1 C1 H1 . . . 118.7 ? C1 C2 C3 . . . 118.0(4) Y C1 C2 H2 . . . 121 ? C3 C2 H2 . . . 121 ? C4 C3 C2 . . . 121.0(4) Y C4 C3 H3 . . . 119.5 ? C2 C3 H3 . . . 119.5 ? C3 C4 C5 . . . 118.7(4) Y C3 C4 H4 . . . 120.6 ? C5 C4 H4 . . . 120.6 ? C4 C5 N1 . . . 123.0(3) Y C4 C5 C6 . . . 119.0(3) Y N1 C5 C6 . . . 118.0(3) Y N2 C6 N4 . . . 125.1(3) Y N2 C6 C5 . . . 117.0(3) Y N4 C6 C5 . . . 117.8(3) Y N5 C7 N4 . . . 125.1(3) Y N5 C7 C14 . . . 117.3(3) Y N4 C7 C14 . . . 117.6(3) Y N5 C8 N2 . . . 124.6(3) Y N5 C8 C9 . . . 117.7(3) Y N2 C8 C9 . . . 117.7(3) Y N3 C9 C10 . . . 122.6(3) Y N3 C9 C8 . . . 117.3(3) Y C10 C9 C8 . . . 120.1(3) Y C11 C10 C9 . . . 119.0(3) Y C11 C10 H10 . . . 120.5 ? C9 C10 H10 . . . 120.5 ? C10 C11 C12 . . . 119.5(3) Y C10 C11 H11 . . . 120.2 ? C12 C11 H11 . . . 120.2 ? C11 C12 C13 . . . 117.7(3) Y C11 C12 H12 . . . 121.1 ? C13 C12 H12 . . . 121.1 ? N3 C13 C12 . . . 123.4(3) Y N3 C13 H13 . . . 118.3 ? C12 C13 H13 . . . 118.3 ? C19 C14 C15 . . . 119.0(3) Y C19 C14 C7 . . . 119.9(3) Y C15 C14 C7 . . . 121.1(3) Y C16 C15 C14 . . . 121.0(3) Y C16 C15 H15 . . . 119.5 ? C14 C15 H15 . . . 119.5 ? C15 C16 C17 . . . 118.6(3) Y C15 C16 H16 . . . 120.7 ? C17 C16 H16 . . . 120.7 ? C18 C17 C16 . . . 121.6(3) Y C18 C17 BR1 . . . 119.0(2) Y C16 C17 BR1 . . . 119.4(2) Y C17 C18 C19 . . . 119.3(3) Y C17 C18 H18 . . . 120.4 ? C19 C18 H18 . . . 120.4 ? C18 C19 C14 . . . 120.6(3) Y C18 C19 H19 . . . 119.7 ? C14 C19 H19 . . . 119.7 ? H12A O12 H12B . . . 113(8) ? H11A O11 H11B . . . 111(7) ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion _geom_torsion_publ_flag C5 N1 C1 C2 . . . . 1.7(8) N N1 C1 C2 C3 . . . . -1.4(8) N C1 C2 C3 C4 . . . . 0.6(8) N C2 C3 C4 C5 . . . . -0.2(7) N C3 C4 C5 N1 . . . . 0.5(7) N C3 C4 C5 C6 . . . . -178.8(4) N C1 N1 C5 C4 . . . . -1.2(7) N C1 N1 C5 C6 . . . . 178.1(4) N C8 N2 C6 N4 . . . . -0.2(5) N C8 N2 C6 C5 . . . . -179.8(3) N C7 N4 C6 N2 . . . . -0.4(5) N C7 N4 C6 C5 . . . . 179.2(3) N C4 C5 C6 N2 . . . . 176.3(4) N N1 C5 C6 N2 . . . . -3.1(5) N C4 C5 C6 N4 . . . . -3.3(5) N N1 C5 C6 N4 . . . . 177.3(3) N C8 N5 C7 N4 . . . . 0.8(5) N C8 N5 C7 C14 . . . . -179.7(3) N C6 N4 C7 N5 . . . . 0.0(5) N C6 N4 C7 C14 . . . . -179.5(3) N C7 N5 C8 N2 . . . . -1.4(5) N C7 N5 C8 C9 . . . . 178.3(3) N C6 N2 C8 N5 . . . . 1.1(5) N C6 N2 C8 C9 . . . . -178.6(3) N C13 N3 C9 C10 . . . . -1.4(5) N C13 N3 C9 C8 . . . . 179.0(3) N N5 C8 C9 N3 . . . . -179.8(3) N N2 C8 C9 N3 . . . . -0.1(5) N N5 C8 C9 C10 . . . . 0.6(5) N N2 C8 C9 C10 . . . . -179.7(3) N N3 C9 C10 C11 . . . . 1.8(5) N C8 C9 C10 C11 . . . . -178.6(3) N C9 C10 C11 C12 . . . . -0.4(6) N C10 C11 C12 C13 . . . . -1.3(6) N C9 N3 C13 C12 . . . . -0.4(6) N C11 C12 C13 N3 . . . . 1.8(6) N N5 C7 C14 C19 . . . . 1.4(5) N N4 C7 C14 C19 . . . . -179.0(3) N N5 C7 C14 C15 . . . . -178.3(3) N N4 C7 C14 C15 . . . . 1.3(5) N C19 C14 C15 C16 . . . . 0.1(5) N C7 C14 C15 C16 . . . . 179.8(3) N C14 C15 C16 C17 . . . . 0.6(5) N C15 C16 C17 C18 . . . . -0.8(5) N C15 C16 C17 BR1 . . . . 176.1(3) N C16 C17 C18 C19 . . . . 0.4(5) N BR1 C17 C18 C19 . . . . -176.6(3) N C17 C18 C19 C14 . . . . 0.3(5) N C15 C14 C19 C18 . . . . -0.5(5) N C7 C14 C19 C18 . . . . 179.7(3) N loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O11 H11A O12 0.84(5) 1.87(8) 2.629(6) 149(10) . O11 H11B O12 0.84(6) 1.90(2) 2.730(6) 168(6) 1_565 O12 H12A N3 0.84(3) 2.15(7) 2.906(4) 151(7) . O12 H12B N1 0.84(7) 2.52(7) 3.096(6) 126(6) . _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 68.58 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.963 _refine_diff_density_min -1.145 _refine_diff_density_rms 0.094