# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2006 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 # 1. SUBMISSION DETAILS _publ_contact_author_name 'Alan H. Cowley' _publ_contact_author_address ; Department of Chemistry and Biochemistry University of Texas-Austin 1 University Station, A5300 Austin, TX 78701 USA ; _publ_contact_author_phone 512-471-7710 _publ_contact_author_fax 512-471-6822 _publ_contact_author_email cowley@mail.utexas.edu _publ_contact_letter ; Please consider this CIF submission for publication in Chem Commun ; # 2. TITLE AND AUTHOR LIST _publ_section_title ; Facile Routes to Alkyl-BIAN ligands ; _publ_section_synopsis ; ; _publ_section_abstract ; ; _publ_section_comment ; ; _publ_section_references ; Allen, F.H. (2002). Acta Cryst. B58, 380-388. Cremer D. & Pople J.A. (1975). J. Am. Chem. Soc. 97, 1358-1367. Altomare A., Burla M.C., Camalli M., Cascarano G.L., Giacovazzo C., Guagliardi A., Moliterni A.G.G., Polidori G.,Spagna R. Sir97. (1999) J. Appl. Cryst. 32, 115-119. Otwinowski, Z. and Minor, W. (1997). Methods in Enzymology, 276, Macromolecular Crystallography, part A, 307-326, C. W. Carter, Jr. and R. M. Sweets, Eds., Academic Press. Sheldrick, G. M. (1998). SHELXTL/PC. Release 5.10. Siemens Analytical X-ray Instruments, Inc., Madison, WI, USA. Sluis, P. v.d. & Spek, A. L. (1990). SQUEEZE. Acta Cryst. A46, 194-201. Spek, A. L. (1998) PLATON, A Multipurpose Crystallographic Tool, Utrecht University, Utrecht, The Netherlands. ; loop_ _publ_author_name A.Cowley 'Nicholas Hill' 'Jennifer Moore' 'Gregor Reeske' 'Kalyan Vasudevan' data_compound_1 _database_code_depnum_ccdc_archive 'CCDC 605399' _audit_creation_method ; manual editing of the .cif file created by SHELXTL Ver. 6.10 ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C20 H24 N2' _chemical_formula_sum 'C20 H24 N2' _chemical_formula_weight 292.41 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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting tetragonal _symmetry_space_group_name_H-M p43 _symmetry_space_group_name_Hall p4cw loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' '-y, x, z+3/4' 'y, -x, z+1/4' _cell_length_a 10.986(5) _cell_length_b 10.986(5) _cell_length_c 13.853(5) _cell_angle_alpha 90.000 _cell_angle_beta 90.000 _cell_angle_gamma 90.000 _cell_volume 1671.9(12) _cell_formula_units_Z 4 _cell_measurement_temperature 153(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.162 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 632 _exptl_absorpt_coefficient_mu 0.068 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.992 _exptl_absorpt_correction_T_max 0.993 _exptl_absorpt_process_details 'DENZO and Scalepack (Otwinoski and Minor, 1997)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 153(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method \w-scan _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3288 _diffrn_reflns_av_R_equivalents 0.0438 _diffrn_reflns_av_sigmaI/netI 0.0754 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.37 _diffrn_reflns_theta_max 27.46 _reflns_number_total 1986 _reflns_number_gt 1421 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect software, Nonius B.V. 1998' _computing_cell_refinement 'Collect software, Nonius B.V. 1998' _computing_data_reduction ; DENZO and Scalepack (Otwinoski and Minor, 1997) ; _computing_structure_solution ; SIR97 - Altomare A., Burla M.C., Camalli M., Cascarano G.L., Giacovazzo C., Guagliardi A., Moliterni A.G.G., Polidori G.,Spagna R. ; _computing_structure_refinement 'XL SHELXTL/PC, Siemens Analytical' _computing_molecular_graphics 'XP SHELXTL/PC, Siemens Analytical' _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^)+(0.0716P)^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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0(10) _refine_ls_number_reflns 1986 _refine_ls_number_parameters 206 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0817 _refine_ls_R_factor_gt 0.0465 _refine_ls_wR_factor_ref 0.1342 _refine_ls_wR_factor_gt 0.1008 _refine_ls_goodness_of_fit_ref 1.082 _refine_ls_restrained_S_all 1.082 _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 C1 C 0.4726(2) 0.1933(2) 0.8497(2) 0.0283(6) Uani 1 1 d . . . C2 C 0.4079(2) 0.3131(2) 0.8504(2) 0.0283(6) Uani 1 1 d . . . C3 C 0.2886(3) 0.3511(3) 0.8515(2) 0.0346(7) Uani 1 1 d . . . H3 H 0.2260 0.2942 0.8526 0.042 Uiso 1 1 calc R . . C4 C 0.2609(3) 0.4775(3) 0.8509(2) 0.0372(7) Uani 1 1 d . . . H4 H 0.1799 0.5018 0.8518 0.045 Uiso 1 1 calc R . . C5 C 0.3505(3) 0.5646(3) 0.8491(2) 0.0376(7) Uani 1 1 d . . . H5 H 0.3294 0.6466 0.8479 0.045 Uiso 1 1 calc R . . C6 C 0.4741(3) 0.5305(3) 0.8490(2) 0.0333(7) Uani 1 1 d . . . C7 C 0.5764(3) 0.6098(3) 0.8474(3) 0.0366(7) Uani 1 1 d . . . H7 H 0.5647 0.6936 0.8456 0.044 Uiso 1 1 calc R . . C8 C 0.6925(3) 0.5628(3) 0.8485(3) 0.0385(8) Uani 1 1 d . . . H8 H 0.7582 0.6162 0.8479 0.046 Uiso 1 1 calc R . . C9 C 0.7153(3) 0.4361(3) 0.8504(2) 0.0353(7) Uani 1 1 d . . . H9 H 0.7946 0.4066 0.8512 0.042 Uiso 1 1 calc R . . C10 C 0.6180(3) 0.3576(3) 0.8511(2) 0.0294(6) Uani 1 1 d . . . C11 C 0.4991(3) 0.4054(2) 0.8498(2) 0.0288(6) Uani 1 1 d . . . C12 C 0.6105(3) 0.2230(2) 0.8541(2) 0.0287(6) Uani 1 1 d . . . C13 C 0.3138(3) 0.0354(3) 0.8355(2) 0.0332(7) Uani 1 1 d . . . C14 C 0.3264(3) -0.1027(3) 0.8267(3) 0.0452(9) Uani 1 1 d . . . H14A H 0.3718 -0.1221 0.7695 0.068 Uiso 1 1 calc R . . H14B H 0.2470 -0.1389 0.8229 0.068 Uiso 1 1 calc R . . H14C H 0.3684 -0.1338 0.8823 0.068 Uiso 1 1 calc R . . C15 C 0.2422(3) 0.0622(3) 0.9277(2) 0.0401(8) Uani 1 1 d . . . H15A H 0.2779 0.0185 0.9807 0.060 Uiso 1 1 calc R . . H15B H 0.1593 0.0368 0.9195 0.060 Uiso 1 1 calc R . . H15C H 0.2447 0.1479 0.9409 0.060 Uiso 1 1 calc R . . C16 C 0.2528(3) 0.0825(3) 0.7435(2) 0.0396(8) Uani 1 1 d . . . H16A H 0.2541 0.1699 0.7434 0.059 Uiso 1 1 calc R . . H16B H 0.1701 0.0546 0.7412 0.059 Uiso 1 1 calc R . . H16C H 0.2961 0.0527 0.6881 0.059 Uiso 1 1 calc R . . C17 C 0.7241(3) 0.0276(3) 0.8642(2) 0.0319(7) Uani 1 1 d . . . C18 C 0.6603(3) -0.0288(3) 0.9514(3) 0.0421(8) Uani 1 1 d . . . H18A H 0.6875 0.0109 1.0093 0.063 Uiso 1 1 calc R . . H18B H 0.6795 -0.1139 0.9549 0.063 Uiso 1 1 calc R . . H18C H 0.5739 -0.0188 0.9450 0.063 Uiso 1 1 calc R . . C19 C 0.6855(3) -0.0321(3) 0.7691(2) 0.0369(8) Uani 1 1 d . . . H19A H 0.5988 -0.0257 0.7619 0.055 Uiso 1 1 calc R . . H19B H 0.7085 -0.1164 0.7697 0.055 Uiso 1 1 calc R . . H19C H 0.7248 0.0083 0.7162 0.055 Uiso 1 1 calc R . . C20 C 0.8614(3) 0.0086(3) 0.8769(3) 0.0422(8) Uani 1 1 d . . . H20A H 0.9042 0.0505 0.8265 0.063 Uiso 1 1 calc R . . H20B H 0.8796 -0.0767 0.8738 0.063 Uiso 1 1 calc R . . H20C H 0.8863 0.0402 0.9385 0.063 Uiso 1 1 calc R . . N1 N 0.4395(2) 0.0817(2) 0.84328(19) 0.0300(6) Uani 1 1 d . . . N2 N 0.7081(2) 0.1607(2) 0.85955(17) 0.0317(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 C1 0.0322(16) 0.0267(16) 0.0261(14) 0.0003(13) -0.0006(14) 0.0027(11) C2 0.0354(17) 0.0236(15) 0.0258(14) -0.0019(12) -0.0012(14) 0.0011(12) C3 0.0377(18) 0.0305(17) 0.0358(16) -0.0004(15) -0.0002(15) 0.0023(12) C4 0.0366(19) 0.0371(18) 0.0379(18) -0.0015(15) -0.0015(16) 0.0111(13) C5 0.051(2) 0.0253(16) 0.0360(17) -0.0003(15) -0.0019(16) 0.0078(14) C6 0.049(2) 0.0276(17) 0.0229(14) -0.0001(13) -0.0015(15) 0.0007(12) C7 0.056(2) 0.0251(16) 0.0285(16) -0.0015(14) 0.0029(16) -0.0035(13) C8 0.050(2) 0.0319(17) 0.0331(16) -0.0005(15) -0.0019(15) -0.0121(14) C9 0.0412(18) 0.0348(18) 0.0298(16) -0.0001(14) 0.0001(15) -0.0057(13) C10 0.0361(17) 0.0278(16) 0.0241(14) -0.0005(13) -0.0024(14) -0.0035(11) C11 0.0400(18) 0.0239(15) 0.0224(13) -0.0007(13) -0.0010(14) -0.0005(11) C12 0.0334(16) 0.0295(16) 0.0233(14) -0.0010(14) -0.0001(13) -0.0011(11) C13 0.0300(17) 0.0244(16) 0.0453(19) -0.0017(13) 0.0034(14) -0.0025(11) C14 0.043(2) 0.0293(19) 0.063(2) -0.0036(16) 0.0037(17) -0.0048(14) C15 0.042(2) 0.0316(19) 0.047(2) -0.0008(14) 0.0055(15) -0.0037(15) C16 0.038(2) 0.0368(19) 0.044(2) -0.0055(14) -0.0048(15) -0.0056(14) C17 0.0334(16) 0.0265(16) 0.0359(18) -0.0001(13) -0.0033(13) 0.0046(12) C18 0.049(2) 0.035(2) 0.0420(19) 0.0082(15) 0.0009(15) 0.0037(15) C19 0.0376(19) 0.0317(18) 0.0415(19) -0.0052(14) -0.0006(14) 0.0033(13) C20 0.0358(19) 0.0400(19) 0.051(2) 0.0005(15) -0.0037(15) 0.0055(14) N1 0.0309(13) 0.0243(13) 0.0348(14) 0.0006(12) 0.0013(11) -0.0015(9) N2 0.0345(14) 0.0289(13) 0.0315(14) -0.0026(11) -0.0021(12) 0.0033(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_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N1 1.281(3) . ? C1 C2 1.496(4) . ? C1 C12 1.551(4) . ? C2 C3 1.376(4) . ? C2 C11 1.426(4) . ? C3 C4 1.420(4) . ? C3 H3 0.9300 . ? C4 C5 1.373(5) . ? C4 H4 0.9300 . ? C5 C6 1.409(4) . ? C5 H5 0.9300 . ? C6 C11 1.402(4) . ? C6 C7 1.422(5) . ? C7 C8 1.376(5) . ? C7 H7 0.9300 . ? C8 C9 1.414(4) . ? C8 H8 0.9300 . ? C9 C10 1.374(4) . ? C9 H9 0.9300 . ? C10 C11 1.407(4) . ? C10 C12 1.481(4) . ? C12 N2 1.274(4) . ? C13 N1 1.476(4) . ? C13 C14 1.528(4) . ? C13 C16 1.530(5) . ? C13 C15 1.529(4) . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 0.9600 . ? C15 H15A 0.9600 . ? C15 H15B 0.9600 . ? C15 H15C 0.9600 . ? C16 H16A 0.9600 . ? C16 H16B 0.9600 . ? C16 H16C 0.9600 . ? C17 N2 1.474(4) . ? C17 C18 1.528(5) . ? C17 C20 1.532(4) . ? C17 C19 1.532(4) . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 0.9600 . ? C20 H20A 0.9600 . ? C20 H20B 0.9600 . ? C20 H20C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 C1 C2 135.0(3) . . ? N1 C1 C12 118.8(2) . . ? C2 C1 C12 106.2(2) . . ? C3 C2 C11 117.0(3) . . ? C3 C2 C1 136.1(3) . . ? C11 C2 C1 106.9(2) . . ? C2 C3 C4 120.0(3) . . ? C2 C3 H3 120.0 . . ? C4 C3 H3 120.0 . . ? C5 C4 C3 121.9(3) . . ? C5 C4 H4 119.1 . . ? C3 C4 H4 119.1 . . ? C4 C5 C6 120.4(3) . . ? C4 C5 H5 119.8 . . ? C6 C5 H5 119.8 . . ? C11 C6 C5 116.7(3) . . ? C11 C6 C7 116.5(3) . . ? C5 C6 C7 126.8(3) . . ? C8 C7 C6 120.2(3) . . ? C8 C7 H7 119.9 . . ? C6 C7 H7 119.9 . . ? C7 C8 C9 122.2(3) . . ? C7 C8 H8 118.9 . . ? C9 C8 H8 118.9 . . ? C10 C9 C8 118.7(3) . . ? C10 C9 H9 120.6 . . ? C8 C9 H9 120.6 . . ? C9 C10 C11 119.2(3) . . ? C9 C10 C12 132.1(3) . . ? C11 C10 C12 108.7(2) . . ? C6 C11 C10 123.2(3) . . ? C6 C11 C2 124.0(3) . . ? C10 C11 C2 112.8(2) . . ? N2 C12 C10 119.5(2) . . ? N2 C12 C1 135.3(3) . . ? C10 C12 C1 105.3(2) . . ? N1 C13 C14 105.3(2) . . ? N1 C13 C16 110.7(2) . . ? C14 C13 C16 108.0(3) . . ? N1 C13 C15 110.7(3) . . ? C14 C13 C15 107.7(3) . . ? C16 C13 C15 114.0(2) . . ? C13 C14 H14A 109.5 . . ? C13 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C13 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C13 C15 H15A 109.5 . . ? C13 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C13 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C13 C16 H16A 109.5 . . ? C13 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C13 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? N2 C17 C18 112.5(3) . . ? N2 C17 C20 105.0(2) . . ? C18 C17 C20 107.8(3) . . ? N2 C17 C19 110.7(2) . . ? C18 C17 C19 112.3(3) . . ? C20 C17 C19 108.3(3) . . ? C17 C18 H18A 109.5 . . ? C17 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C17 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C17 C19 H19A 109.5 . . ? C17 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C17 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? 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 . . ? C1 N1 C13 126.9(2) . . ? C12 N2 C17 129.5(3) . . ? 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 _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 C1 C2 C3 5.9(7) . . . . ? C12 C1 C2 C3 -177.0(4) . . . . ? N1 C1 C2 C11 -174.2(4) . . . . ? C12 C1 C2 C11 2.9(3) . . . . ? C11 C2 C3 C4 0.7(5) . . . . ? C1 C2 C3 C4 -179.4(3) . . . . ? C2 C3 C4 C5 0.1(5) . . . . ? C3 C4 C5 C6 -0.8(5) . . . . ? C4 C5 C6 C11 0.7(5) . . . . ? C4 C5 C6 C7 -179.9(3) . . . . ? C11 C6 C7 C8 -1.2(5) . . . . ? C5 C6 C7 C8 179.4(3) . . . . ? C6 C7 C8 C9 0.5(5) . . . . ? C7 C8 C9 C10 0.1(5) . . . . ? C8 C9 C10 C11 0.0(5) . . . . ? C8 C9 C10 C12 -179.2(3) . . . . ? C5 C6 C11 C10 -179.1(3) . . . . ? C7 C6 C11 C10 1.4(5) . . . . ? C5 C6 C11 C2 0.2(5) . . . . ? C7 C6 C11 C2 -179.3(3) . . . . ? C9 C10 C11 C6 -0.8(5) . . . . ? C12 C10 C11 C6 178.6(3) . . . . ? C9 C10 C11 C2 179.8(3) . . . . ? C12 C10 C11 C2 -0.8(4) . . . . ? C3 C2 C11 C6 -0.8(5) . . . . ? C1 C2 C11 C6 179.2(3) . . . . ? C3 C2 C11 C10 178.5(3) . . . . ? C1 C2 C11 C10 -1.4(4) . . . . ? C9 C10 C12 N2 2.0(5) . . . . ? C11 C10 C12 N2 -177.3(3) . . . . ? C9 C10 C12 C1 -178.2(3) . . . . ? C11 C10 C12 C1 2.6(3) . . . . ? N1 C1 C12 N2 -5.8(5) . . . . ? C2 C1 C12 N2 176.5(3) . . . . ? N1 C1 C12 C10 174.4(3) . . . . ? C2 C1 C12 C10 -3.3(3) . . . . ? C2 C1 N1 C13 -1.2(6) . . . . ? C12 C1 N1 C13 -178.1(3) . . . . ? C14 C13 N1 C1 178.3(3) . . . . ? C16 C13 N1 C1 61.7(4) . . . . ? C15 C13 N1 C1 -65.6(4) . . . . ? C10 C12 N2 C17 179.5(3) . . . . ? C1 C12 N2 C17 -0.3(5) . . . . ? C18 C17 N2 C12 -59.2(4) . . . . ? C20 C17 N2 C12 -176.1(3) . . . . ? C19 C17 N2 C12 67.3(4) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.46 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.271 _refine_diff_density_min -0.265 _refine_diff_density_rms 0.095 data_compound_2 _database_code_depnum_ccdc_archive 'CCDC 605400' _audit_creation_method ; manual editing of the .cif file created by SHELXTL Ver. 6.10 ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C32 H36 N2 ' _chemical_formula_sum 'C32 H36 N2' _chemical_formula_weight 448.63 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' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M p-1 _symmetry_space_group_name_Hall -p1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.965(5) _cell_length_b 11.003(5) _cell_length_c 11.964(5) _cell_angle_alpha 92.589(5) _cell_angle_beta 105.670(5) _cell_angle_gamma 108.860(5) _cell_volume 1182.5(9) _cell_formula_units_Z 2 _cell_measurement_temperature 153(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description needle _exptl_crystal_colour yellow _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.260 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 484 _exptl_absorpt_coefficient_mu 0.073 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.990 _exptl_absorpt_correction_T_max 0.998 _exptl_absorpt_process_details 'DENZO and Scalepack (Otwinoski and Minor, 1997)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 153(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method \w-scan _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8926 _diffrn_reflns_av_R_equivalents 0.0746 _diffrn_reflns_av_sigmaI/netI 0.1940 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.79 _diffrn_reflns_theta_max 27.46 _reflns_number_total 5361 _reflns_number_gt 2152 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect software, Nonius B.V. 1998' _computing_cell_refinement 'Collect software, Nonius B.V. 1998' _computing_data_reduction ; DENZO and Scalepack (Otwinoski and Minor, 1997) ; _computing_structure_solution ; SIR97 - Altomare A., Burla M.C., Camalli M., Cascarano G.L., Giacovazzo C., Guagliardi A., Moliterni A.G.G., Polidori G.,Spagna R. ; _computing_structure_refinement 'XL SHELXTL/PC, Siemens Analytical' _computing_molecular_graphics 'XP SHELXTL/PC, Siemens Analytical' _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^)+(0.0879P)^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 5361 _refine_ls_number_parameters 307 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.2018 _refine_ls_R_factor_gt 0.0595 _refine_ls_wR_factor_ref 0.2003 _refine_ls_wR_factor_gt 0.1194 _refine_ls_goodness_of_fit_ref 0.958 _refine_ls_restrained_S_all 0.958 _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 C1 C 0.7406(3) 0.4939(3) 0.4831(3) 0.0250(8) Uani 1 1 d . . . C2 C 0.6507(3) 0.4105(3) 0.3653(3) 0.0240(8) Uani 1 1 d . . . C3 C 0.5459(3) 0.2867(3) 0.3281(3) 0.0277(8) Uani 1 1 d . . . H3 H 0.5148 0.2339 0.3835 0.033 Uiso 1 1 calc R . . C4 C 0.4857(3) 0.2397(3) 0.2065(3) 0.0288(8) Uani 1 1 d . . . H4 H 0.4143 0.1544 0.1820 0.035 Uiso 1 1 calc R . . C5 C 0.5260(4) 0.3119(3) 0.1226(3) 0.0315(9) Uani 1 1 d . . . H5 H 0.4817 0.2768 0.0419 0.038 Uiso 1 1 calc R . . C6 C 0.6333(3) 0.4384(3) 0.1560(3) 0.0254(8) Uani 1 1 d . . . C7 C 0.6902(4) 0.5245(3) 0.0813(3) 0.0314(9) Uani 1 1 d . . . H7 H 0.6546 0.4985 -0.0012 0.038 Uiso 1 1 calc R . . C8 C 0.7962(3) 0.6451(3) 0.1273(3) 0.0303(8) Uani 1 1 d . . . H8 H 0.8331 0.7007 0.0757 0.036 Uiso 1 1 calc R . . C9 C 0.8513(3) 0.6884(3) 0.2491(3) 0.0279(8) Uani 1 1 d . . . H9 H 0.9239 0.7723 0.2794 0.033 Uiso 1 1 calc R . . C10 C 0.7982(3) 0.6071(3) 0.3229(3) 0.0247(8) Uani 1 1 d . . . C11 C 0.6918(3) 0.4834(3) 0.2772(3) 0.0236(8) Uani 1 1 d . . . C12 C 0.8328(3) 0.6264(3) 0.4531(3) 0.0246(8) Uani 1 1 d . . . C13 C 0.6878(3) 0.3630(3) 0.6385(3) 0.0249(8) Uani 1 1 d . . . C14 C 0.7526(3) 0.4006(3) 0.7726(2) 0.0244(8) Uani 1 1 d . . . H14A H 0.8622 0.4257 0.7954 0.029 Uiso 1 1 calc R . . H14B H 0.7289 0.4763 0.7972 0.029 Uiso 1 1 calc R . . C15 C 0.6892(3) 0.2878(3) 0.8352(3) 0.0284(8) Uani 1 1 d . . . H15 H 0.7327 0.3140 0.9221 0.034 Uiso 1 1 calc R . . C16 C 0.5192(3) 0.2496(3) 0.8003(3) 0.0281(8) Uani 1 1 d . . . H16A H 0.4771 0.1755 0.8394 0.034 Uiso 1 1 calc R . . H16B H 0.4929 0.3234 0.8257 0.034 Uiso 1 1 calc R . . C17 C 0.4543(3) 0.2119(3) 0.6671(3) 0.0258(8) Uani 1 1 d . . . H17 H 0.3437 0.1871 0.6443 0.031 Uiso 1 1 calc R . . C18 C 0.5187(3) 0.3280(3) 0.6082(3) 0.0248(8) Uani 1 1 d . . . H18A H 0.4960 0.4032 0.6355 0.030 Uiso 1 1 calc R . . H18B H 0.4729 0.3064 0.5220 0.030 Uiso 1 1 calc R . . C19 C 0.7292(3) 0.2468(3) 0.6043(3) 0.0248(8) Uani 1 1 d . . . H19A H 0.6907 0.2211 0.5181 0.030 Uiso 1 1 calc R . . H19B H 0.8388 0.2715 0.6280 0.030 Uiso 1 1 calc R . . C20 C 0.6632(3) 0.1330(3) 0.6645(3) 0.0273(8) Uani 1 1 d . . . H20 H 0.6883 0.0569 0.6403 0.033 Uiso 1 1 calc R . . C21 C 0.4938(3) 0.0970(3) 0.6284(3) 0.0298(8) Uani 1 1 d . . . H21A H 0.4521 0.0727 0.5421 0.036 Uiso 1 1 calc R . . H21B H 0.4498 0.0213 0.6652 0.036 Uiso 1 1 calc R . . C22 C 0.7271(4) 0.1719(3) 0.7973(3) 0.0294(8) Uani 1 1 d . . . H22A H 0.6854 0.0979 0.8367 0.035 Uiso 1 1 calc R . . H22B H 0.8365 0.1947 0.8209 0.035 Uiso 1 1 calc R . . C23 C 0.9743(3) 0.7821(3) 0.6379(3) 0.0237(8) Uani 1 1 d . . . C24 C 0.8485(3) 0.7791(3) 0.6903(3) 0.0266(8) Uani 1 1 d . . . H24A H 0.7898 0.8290 0.6471 0.032 Uiso 1 1 calc R . . H24B H 0.7812 0.6884 0.6827 0.032 Uiso 1 1 calc R . . C25 C 0.9153(3) 0.8384(3) 0.8196(3) 0.0292(8) Uani 1 1 d . . . H25 H 0.8331 0.8346 0.8537 0.035 Uiso 1 1 calc R . . C26 C 1.0155(3) 0.9803(3) 0.8318(3) 0.0313(8) Uani 1 1 d . . . H26A H 0.9568 1.0307 0.7894 0.038 Uiso 1 1 calc R . . H26B H 1.0567 1.0189 0.9156 0.038 Uiso 1 1 calc R . . C27 C 1.1420(3) 0.9859(3) 0.7807(3) 0.0268(8) Uani 1 1 d . . . H27 H 1.2072 1.0783 0.7872 0.032 Uiso 1 1 calc R . . C28 C 1.0757(3) 0.9248(3) 0.6516(3) 0.0269(8) Uani 1 1 d . . . H28A H 1.1571 0.9293 0.6176 0.032 Uiso 1 1 calc R . . H28B H 1.0174 0.9747 0.6078 0.032 Uiso 1 1 calc R . . C29 C 1.2335(3) 0.9096(3) 0.8478(3) 0.0310(8) Uani 1 1 d . . . H29A H 1.3165 0.9141 0.8157 0.037 Uiso 1 1 calc R . . H29B H 1.2762 0.9478 0.9317 0.037 Uiso 1 1 calc R . . C30 C 1.0074(3) 0.7629(3) 0.8872(3) 0.0310(8) Uani 1 1 d . . . H30A H 0.9433 0.6714 0.8815 0.037 Uiso 1 1 calc R . . H30B H 1.0489 0.8011 0.9711 0.037 Uiso 1 1 calc R . . C31 C 1.0694(3) 0.7089(3) 0.7064(3) 0.0261(8) Uani 1 1 d . . . H31A H 1.1514 0.7135 0.6730 0.031 Uiso 1 1 calc R . . H31B H 1.0077 0.6164 0.6991 0.031 Uiso 1 1 calc R . . C32 C 1.1339(3) 0.7686(3) 0.8360(3) 0.0278(8) Uani 1 1 d . . . H32 H 1.1936 0.7187 0.8799 0.033 Uiso 1 1 calc R . . N1 N 0.7577(3) 0.4799(3) 0.5902(2) 0.0267(7) Uani 1 1 d . . . N2 N 0.9214(3) 0.7361(3) 0.5106(2) 0.0270(7) 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 C1 0.0228(17) 0.030(2) 0.027(2) 0.0061(16) 0.0105(15) 0.0133(15) C2 0.0248(18) 0.032(2) 0.0213(18) 0.0047(16) 0.0081(15) 0.0162(16) C3 0.0255(18) 0.031(2) 0.028(2) 0.0033(16) 0.0085(15) 0.0105(17) C4 0.0264(19) 0.028(2) 0.031(2) -0.0033(17) 0.0074(16) 0.0103(16) C5 0.035(2) 0.038(2) 0.0217(19) -0.0019(17) 0.0054(16) 0.0164(18) C6 0.0279(18) 0.029(2) 0.0244(19) 0.0024(16) 0.0080(15) 0.0163(17) C7 0.036(2) 0.039(2) 0.0234(19) 0.0040(17) 0.0083(16) 0.0204(19) C8 0.034(2) 0.038(2) 0.028(2) 0.0127(17) 0.0152(16) 0.0178(18) C9 0.0305(19) 0.029(2) 0.028(2) 0.0068(16) 0.0111(16) 0.0137(16) C10 0.0254(18) 0.032(2) 0.0245(19) 0.0056(16) 0.0089(15) 0.0183(17) C11 0.0226(17) 0.030(2) 0.0242(19) 0.0041(16) 0.0081(15) 0.0154(16) C12 0.0240(18) 0.028(2) 0.0274(19) 0.0063(16) 0.0102(15) 0.0140(17) C13 0.0243(17) 0.029(2) 0.0223(18) 0.0049(15) 0.0077(15) 0.0092(15) C14 0.0266(18) 0.0228(19) 0.0226(18) 0.0025(15) 0.0078(15) 0.0066(15) C15 0.0350(19) 0.029(2) 0.0201(18) 0.0045(16) 0.0087(15) 0.0094(16) C16 0.035(2) 0.025(2) 0.0277(19) 0.0069(16) 0.0149(16) 0.0092(16) C17 0.0247(17) 0.030(2) 0.0245(19) 0.0032(16) 0.0103(15) 0.0094(16) C18 0.0253(18) 0.028(2) 0.0237(18) 0.0017(15) 0.0087(15) 0.0125(15) C19 0.0216(17) 0.032(2) 0.0241(18) 0.0038(16) 0.0073(15) 0.0129(16) C20 0.0299(19) 0.026(2) 0.0276(19) 0.0015(16) 0.0074(15) 0.0132(16) C21 0.0319(19) 0.026(2) 0.0273(19) -0.0001(16) 0.0088(16) 0.0056(16) C22 0.0304(19) 0.027(2) 0.027(2) 0.0070(16) 0.0035(15) 0.0096(16) C23 0.0241(17) 0.0248(19) 0.0211(18) 0.0041(15) 0.0058(14) 0.0077(15) C24 0.0214(17) 0.029(2) 0.0299(19) 0.0029(16) 0.0083(15) 0.0092(15) C25 0.0249(18) 0.030(2) 0.031(2) -0.0028(16) 0.0118(15) 0.0066(16) C26 0.0292(19) 0.033(2) 0.031(2) -0.0008(17) 0.0074(16) 0.0120(17) C27 0.0275(18) 0.0206(19) 0.028(2) 0.0005(15) 0.0063(15) 0.0046(15) C28 0.0236(18) 0.026(2) 0.033(2) 0.0054(16) 0.0101(16) 0.0094(16) C29 0.0262(18) 0.037(2) 0.0271(19) 0.0008(17) 0.0061(15) 0.0096(17) C30 0.034(2) 0.032(2) 0.0224(19) 0.0018(16) 0.0069(15) 0.0069(17) C31 0.0246(18) 0.027(2) 0.0292(19) 0.0048(16) 0.0103(15) 0.0102(15) C32 0.0261(18) 0.029(2) 0.029(2) 0.0081(16) 0.0070(15) 0.0113(16) N1 0.0267(15) 0.0296(17) 0.0260(17) 0.0081(13) 0.0095(12) 0.0111(13) N2 0.0293(16) 0.0260(17) 0.0269(16) 0.0026(14) 0.0082(13) 0.0117(14) _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 C1 N1 1.270(4) . ? C1 C2 1.516(4) . ? C1 C12 1.567(4) . ? C2 C3 1.385(4) . ? C2 C11 1.422(4) . ? C3 C4 1.415(4) . ? C3 H3 0.9500 . ? C4 C5 1.374(4) . ? C4 H4 0.9500 . ? C5 C6 1.413(5) . ? C5 H5 0.9500 . ? C6 C11 1.407(4) . ? C6 C7 1.421(4) . ? C7 C8 1.376(5) . ? C7 H7 0.9500 . ? C8 C9 1.410(4) . ? C8 H8 0.9500 . ? C9 C10 1.370(4) . ? C9 H9 0.9500 . ? C10 C11 1.401(4) . ? C10 C12 1.491(4) . ? C12 N2 1.272(4) . ? C13 N1 1.476(4) . ? C13 C18 1.535(4) . ? C13 C19 1.536(4) . ? C13 C14 1.539(4) . ? C14 C15 1.527(4) . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C15 C22 1.526(4) . ? C15 C16 1.537(4) . ? C15 H15 1.0000 . ? C16 C17 1.529(4) . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? C17 C21 1.529(4) . ? C17 C18 1.528(4) . ? C17 H17 1.0000 . ? C18 H18A 0.9900 . ? C18 H18B 0.9900 . ? C19 C20 1.524(4) . ? C19 H19A 0.9900 . ? C19 H19B 0.9900 . ? C20 C22 1.527(4) . ? C20 C21 1.534(4) . ? C20 H20 1.0000 . ? C21 H21A 0.9900 . ? C21 H21B 0.9900 . ? C22 H22A 0.9900 . ? C22 H22B 0.9900 . ? C23 N2 1.476(4) . ? C23 C31 1.533(4) . ? C23 C28 1.542(4) . ? C23 C24 1.538(4) . ? C24 C25 1.527(4) . ? C24 H24A 0.9900 . ? C24 H24B 0.9900 . ? C25 C30 1.529(4) . ? C25 C26 1.533(5) . ? C25 H25 1.0000 . ? C26 C27 1.529(4) . ? C26 H26A 0.9900 . ? C26 H26B 0.9900 . ? C27 C29 1.531(4) . ? C27 C28 1.530(4) . ? C27 H27 1.0000 . ? C28 H28A 0.9900 . ? C28 H28B 0.9900 . ? C29 C32 1.523(4) . ? C29 H29A 0.9900 . ? C29 H29B 0.9900 . ? C30 C32 1.530(4) . ? C30 H30A 0.9900 . ? C30 H30B 0.9900 . ? C31 C32 1.531(4) . ? C31 H31A 0.9900 . ? C31 H31B 0.9900 . ? C32 H32 1.0000 . ? 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 N1 C1 C2 136.3(3) . . ? N1 C1 C12 118.5(3) . . ? C2 C1 C12 105.1(3) . . ? C3 C2 C11 117.1(3) . . ? C3 C2 C1 135.5(3) . . ? C11 C2 C1 107.4(3) . . ? C2 C3 C4 119.3(3) . . ? C2 C3 H3 120.4 . . ? C4 C3 H3 120.4 . . ? C5 C4 C3 122.8(3) . . ? C5 C4 H4 118.6 . . ? C3 C4 H4 118.6 . . ? C4 C5 C6 120.1(3) . . ? C4 C5 H5 119.9 . . ? C6 C5 H5 119.9 . . ? C11 C6 C5 116.2(3) . . ? C11 C6 C7 116.4(3) . . ? C5 C6 C7 127.4(3) . . ? C8 C7 C6 120.7(3) . . ? C8 C7 H7 119.7 . . ? C6 C7 H7 119.7 . . ? C7 C8 C9 121.7(3) . . ? C7 C8 H8 119.1 . . ? C9 C8 H8 119.1 . . ? C10 C9 C8 118.7(3) . . ? C10 C9 H9 120.7 . . ? C8 C9 H9 120.7 . . ? C9 C10 C11 120.1(3) . . ? C9 C10 C12 130.8(3) . . ? C11 C10 C12 109.1(3) . . ? C10 C11 C6 122.4(3) . . ? C10 C11 C2 113.1(3) . . ? C6 C11 C2 124.5(3) . . ? N2 C12 C10 118.7(3) . . ? N2 C12 C1 136.2(3) . . ? C10 C12 C1 105.1(3) . . ? N1 C13 C18 112.2(2) . . ? N1 C13 C19 112.6(2) . . ? C18 C13 C19 111.8(3) . . ? N1 C13 C14 105.1(3) . . ? C18 C13 C14 107.1(2) . . ? C19 C13 C14 107.6(2) . . ? C15 C14 C13 111.0(3) . . ? C15 C14 H14A 109.4 . . ? C13 C14 H14A 109.4 . . ? C15 C14 H14B 109.4 . . ? C13 C14 H14B 109.4 . . ? H14A C14 H14B 108.0 . . ? C14 C15 C22 109.1(2) . . ? C14 C15 C16 109.3(3) . . ? C22 C15 C16 108.9(3) . . ? C14 C15 H15 109.9 . . ? C22 C15 H15 109.9 . . ? C16 C15 H15 109.9 . . ? C17 C16 C15 109.4(2) . . ? C17 C16 H16A 109.8 . . ? C15 C16 H16A 109.8 . . ? C17 C16 H16B 109.8 . . ? C15 C16 H16B 109.8 . . ? H16A C16 H16B 108.2 . . ? C21 C17 C18 109.9(2) . . ? C21 C17 C16 109.6(3) . . ? C18 C17 C16 109.1(3) . . ? C21 C17 H17 109.4 . . ? C18 C17 H17 109.4 . . ? C16 C17 H17 109.4 . . ? C17 C18 C13 109.7(2) . . ? C17 C18 H18A 109.7 . . ? C13 C18 H18A 109.7 . . ? C17 C18 H18B 109.7 . . ? C13 C18 H18B 109.7 . . ? H18A C18 H18B 108.2 . . ? C20 C19 C13 109.8(2) . . ? C20 C19 H19A 109.7 . . ? C13 C19 H19A 109.7 . . ? C20 C19 H19B 109.7 . . ? C13 C19 H19B 109.7 . . ? H19A C19 H19B 108.2 . . ? C19 C20 C22 109.4(3) . . ? C19 C20 C21 109.2(3) . . ? C22 C20 C21 109.5(2) . . ? C19 C20 H20 109.6 . . ? C22 C20 H20 109.6 . . ? C21 C20 H20 109.6 . . ? C17 C21 C20 110.0(3) . . ? C17 C21 H21A 109.7 . . ? C20 C21 H21A 109.7 . . ? C17 C21 H21B 109.7 . . ? C20 C21 H21B 109.7 . . ? H21A C21 H21B 108.2 . . ? C15 C22 C20 110.0(3) . . ? C15 C22 H22A 109.7 . . ? C20 C22 H22A 109.7 . . ? C15 C22 H22B 109.7 . . ? C20 C22 H22B 109.7 . . ? H22A C22 H22B 108.2 . . ? N2 C23 C31 112.1(2) . . ? N2 C23 C28 105.1(2) . . ? C31 C23 C28 107.4(2) . . ? N2 C23 C24 113.4(2) . . ? C31 C23 C24 110.5(3) . . ? C28 C23 C24 107.9(2) . . ? C25 C24 C23 109.4(2) . . ? C25 C24 H24A 109.8 . . ? C23 C24 H24A 109.8 . . ? C25 C24 H24B 109.8 . . ? C23 C24 H24B 109.8 . . ? H24A C24 H24B 108.2 . . ? C30 C25 C24 110.4(3) . . ? C30 C25 C26 109.0(3) . . ? C24 C25 C26 110.1(3) . . ? C30 C25 H25 109.1 . . ? C24 C25 H25 109.1 . . ? C26 C25 H25 109.1 . . ? C27 C26 C25 109.1(3) . . ? C27 C26 H26A 109.9 . . ? C25 C26 H26A 109.9 . . ? C27 C26 H26B 109.9 . . ? C25 C26 H26B 109.9 . . ? H26A C26 H26B 108.3 . . ? C29 C27 C28 109.2(2) . . ? C29 C27 C26 109.6(3) . . ? C28 C27 C26 108.9(3) . . ? C29 C27 H27 109.7 . . ? C28 C27 H27 109.7 . . ? C26 C27 H27 109.7 . . ? C27 C28 C23 111.3(3) . . ? C27 C28 H28A 109.4 . . ? C23 C28 H28A 109.4 . . ? C27 C28 H28B 109.4 . . ? C23 C28 H28B 109.4 . . ? H28A C28 H28B 108.0 . . ? C32 C29 C27 109.4(3) . . ? C32 C29 H29A 109.8 . . ? C27 C29 H29A 109.8 . . ? C32 C29 H29B 109.8 . . ? C27 C29 H29B 109.8 . . ? H29A C29 H29B 108.2 . . ? C25 C30 C32 109.5(3) . . ? C25 C30 H30A 109.8 . . ? C32 C30 H30A 109.8 . . ? C25 C30 H30B 109.8 . . ? C32 C30 H30B 109.8 . . ? H30A C30 H30B 108.2 . . ? C23 C31 C32 110.2(2) . . ? C23 C31 H31A 109.6 . . ? C32 C31 H31A 109.6 . . ? C23 C31 H31B 109.6 . . ? C32 C31 H31B 109.6 . . ? H31A C31 H31B 108.1 . . ? C29 C32 C31 109.8(3) . . ? C29 C32 C30 109.2(3) . . ? C31 C32 C30 109.6(2) . . ? C29 C32 H32 109.4 . . ? C31 C32 H32 109.4 . . ? C30 C32 H32 109.4 . . ? C1 N1 C13 127.8(3) . . ? C12 N2 C23 130.3(3) . . ? 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 _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 C1 C2 C3 3.5(6) . . . . ? C12 C1 C2 C3 -178.1(3) . . . . ? N1 C1 C2 C11 -175.6(3) . . . . ? C12 C1 C2 C11 2.8(3) . . . . ? C11 C2 C3 C4 -0.1(4) . . . . ? C1 C2 C3 C4 -179.2(3) . . . . ? C2 C3 C4 C5 -0.3(4) . . . . ? C3 C4 C5 C6 0.8(5) . . . . ? C4 C5 C6 C11 -0.8(4) . . . . ? C4 C5 C6 C7 178.3(3) . . . . ? C11 C6 C7 C8 -0.3(4) . . . . ? C5 C6 C7 C8 -179.4(3) . . . . ? C6 C7 C8 C9 -0.6(5) . . . . ? C7 C8 C9 C10 0.5(4) . . . . ? C8 C9 C10 C11 0.4(4) . . . . ? C8 C9 C10 C12 -178.8(3) . . . . ? C9 C10 C11 C6 -1.2(4) . . . . ? C12 C10 C11 C6 178.0(3) . . . . ? C9 C10 C11 C2 178.8(3) . . . . ? C12 C10 C11 C2 -1.9(3) . . . . ? C5 C6 C11 C10 -179.6(3) . . . . ? C7 C6 C11 C10 1.2(4) . . . . ? C5 C6 C11 C2 0.4(4) . . . . ? C7 C6 C11 C2 -178.8(3) . . . . ? C3 C2 C11 C10 -180.0(3) . . . . ? C1 C2 C11 C10 -0.7(3) . . . . ? C3 C2 C11 C6 0.1(4) . . . . ? C1 C2 C11 C6 179.4(3) . . . . ? C9 C10 C12 N2 3.1(5) . . . . ? C11 C10 C12 N2 -176.1(3) . . . . ? C9 C10 C12 C1 -177.3(3) . . . . ? C11 C10 C12 C1 3.5(3) . . . . ? N1 C1 C12 N2 -5.5(5) . . . . ? C2 C1 C12 N2 175.8(3) . . . . ? N1 C1 C12 C10 175.0(3) . . . . ? C2 C1 C12 C10 -3.8(3) . . . . ? N1 C13 C14 C15 179.8(2) . . . . ? C18 C13 C14 C15 60.3(3) . . . . ? C19 C13 C14 C15 -60.0(3) . . . . ? C13 C14 C15 C22 59.5(3) . . . . ? C13 C14 C15 C16 -59.5(3) . . . . ? C14 C15 C16 C17 58.5(3) . . . . ? C22 C15 C16 C17 -60.6(3) . . . . ? C15 C16 C17 C21 60.1(3) . . . . ? C15 C16 C17 C18 -60.3(3) . . . . ? C21 C17 C18 C13 -57.4(3) . . . . ? C16 C17 C18 C13 62.7(3) . . . . ? N1 C13 C18 C17 -176.3(2) . . . . ? C19 C13 C18 C17 56.1(3) . . . . ? C14 C13 C18 C17 -61.5(3) . . . . ? N1 C13 C19 C20 175.7(2) . . . . ? C18 C13 C19 C20 -57.0(3) . . . . ? C14 C13 C19 C20 60.4(3) . . . . ? C13 C19 C20 C22 -61.3(3) . . . . ? C13 C19 C20 C21 58.5(3) . . . . ? C18 C17 C21 C20 60.7(3) . . . . ? C16 C17 C21 C20 -59.1(3) . . . . ? C19 C20 C21 C17 -61.1(3) . . . . ? C22 C20 C21 C17 58.7(3) . . . . ? C14 C15 C22 C20 -58.6(3) . . . . ? C16 C15 C22 C20 60.6(3) . . . . ? C19 C20 C22 C15 60.0(3) . . . . ? C21 C20 C22 C15 -59.7(3) . . . . ? N2 C23 C24 C25 -175.5(3) . . . . ? C31 C23 C24 C25 57.6(3) . . . . ? C28 C23 C24 C25 -59.5(3) . . . . ? C23 C24 C25 C30 -59.0(3) . . . . ? C23 C24 C25 C26 61.4(3) . . . . ? C30 C25 C26 C27 60.4(3) . . . . ? C24 C25 C26 C27 -60.8(3) . . . . ? C25 C26 C27 C29 -60.3(3) . . . . ? C25 C26 C27 C28 59.1(3) . . . . ? C29 C27 C28 C23 59.7(3) . . . . ? C26 C27 C28 C23 -59.9(3) . . . . ? N2 C23 C28 C27 -179.0(2) . . . . ? C31 C23 C28 C27 -59.4(3) . . . . ? C24 C23 C28 C27 59.7(3) . . . . ? C28 C27 C29 C32 -58.9(3) . . . . ? C26 C27 C29 C32 60.3(3) . . . . ? C24 C25 C30 C32 60.4(3) . . . . ? C26 C25 C30 C32 -60.7(3) . . . . ? N2 C23 C31 C32 174.5(2) . . . . ? C28 C23 C31 C32 59.6(3) . . . . ? C24 C23 C31 C32 -57.9(3) . . . . ? C27 C29 C32 C31 60.1(3) . . . . ? C27 C29 C32 C30 -60.2(3) . . . . ? C23 C31 C32 C29 -61.3(3) . . . . ? C23 C31 C32 C30 58.7(3) . . . . ? C25 C30 C32 C29 60.7(3) . . . . ? C25 C30 C32 C31 -59.7(3) . . . . ? C2 C1 N1 C13 0.9(5) . . . . ? C12 C1 N1 C13 -177.3(2) . . . . ? C18 C13 N1 C1 -65.7(4) . . . . ? C19 C13 N1 C1 61.4(4) . . . . ? C14 C13 N1 C1 178.3(3) . . . . ? C10 C12 N2 C23 179.7(3) . . . . ? C1 C12 N2 C23 0.2(6) . . . . ? C31 C23 N2 C12 65.3(4) . . . . ? C28 C23 N2 C12 -178.4(3) . . . . ? C24 C23 N2 C12 -60.8(4) . . . . ? _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 27.46 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.320 _refine_diff_density_min -0.401 _refine_diff_density_rms 0.096 data_compound_7 _database_code_depnum_ccdc_archive 'CCDC 605401' _audit_creation_method ; manual editing of the .cif file created by SHELXTL Ver. 6.10 ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C20 H24 Cl2 N2 Zn, C2 H3 N' _chemical_formula_sum 'C22 H27 Cl2 N3 Zn' _chemical_formula_weight 469.74 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M cc _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' _cell_length_a 11.276(5) _cell_length_b 20.656(5) _cell_length_c 9.430(5) _cell_angle_alpha 90.000(5) _cell_angle_beta 93.968(5) _cell_angle_gamma 90.000(5) _cell_volume 2191.1(16) _cell_formula_units_Z 4 _cell_measurement_temperature 153(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.424 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 976 _exptl_absorpt_coefficient_mu 1.377 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7702 _exptl_absorpt_correction_T_max 0.8746 _exptl_absorpt_process_details 'DENZO and Scalepack (Otwinoski and Minor, 1997)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 153(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method \w-scan _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4357 _diffrn_reflns_av_R_equivalents 0.0106 _diffrn_reflns_av_sigmaI/netI 0.0653 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -26 _diffrn_reflns_limit_k_max 25 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 3.47 _diffrn_reflns_theta_max 27.48 _reflns_number_total 4350 _reflns_number_gt 3557 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect software, Nonius B.V. 1998' _computing_cell_refinement 'Collect software, Nonius B.V. 1998' _computing_data_reduction ; DENZO and Scalepack (Otwinoski and Minor, 1997) ; _computing_structure_solution ; SIR97 - Altomare A., Burla M.C., Camalli M., Cascarano G.L., Giacovazzo C., Guagliardi A., Moliterni A.G.G., Polidori G.,Spagna R. ; _computing_structure_refinement 'XL SHELXTL/PC, Siemens Analytical' _computing_molecular_graphics 'XP SHELXTL/PC, Siemens Analytical' _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^)+(0.0291P)^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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.482(10) _refine_ls_number_reflns 4350 _refine_ls_number_parameters 261 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0581 _refine_ls_R_factor_gt 0.0374 _refine_ls_wR_factor_ref 0.0778 _refine_ls_wR_factor_gt 0.0707 _refine_ls_goodness_of_fit_ref 1.068 _refine_ls_restrained_S_all 1.068 _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 C1 C -0.0339(3) 0.07122(16) 0.0407(4) 0.0217(8) Uani 1 1 d . . . C2 C -0.0474(3) -0.00023(17) 0.0598(4) 0.0224(8) Uani 1 1 d . . . C3 C -0.1261(3) -0.03934(17) 0.1227(4) 0.0322(9) Uani 1 1 d . . . H3 H -0.1900 -0.0215 0.1662 0.039 Uiso 1 1 calc R . . C4 C -0.1092(3) -0.10766(19) 0.1210(4) 0.0341(10) Uani 1 1 d . . . H4 H -0.1613 -0.1342 0.1666 0.041 Uiso 1 1 calc R . . C5 C -0.0184(3) -0.13504(16) 0.0539(4) 0.0319(10) Uani 1 1 d . . . H5 H -0.0114 -0.1799 0.0519 0.038 Uiso 1 1 calc R . . C6 C 0.0650(3) -0.09667(17) -0.0123(4) 0.0272(9) Uani 1 1 d . . . C7 C 0.1637(3) -0.11870(18) -0.0825(4) 0.0306(9) Uani 1 1 d . . . H7 H 0.1756 -0.1629 -0.0935 0.037 Uiso 1 1 calc R . . C8 C 0.2418(3) -0.07601(18) -0.1342(4) 0.0351(9) Uani 1 1 d . . . H8 H 0.3056 -0.0919 -0.1812 0.042 Uiso 1 1 calc R . . C9 C 0.2294(3) -0.00811(17) -0.1190(4) 0.0303(8) Uani 1 1 d . . . H9 H 0.2850 0.0199 -0.1541 0.036 Uiso 1 1 calc R . . C10 C 0.1334(3) 0.01599(16) -0.0512(4) 0.0236(8) Uani 1 1 d . . . C11 C 0.0505(3) -0.02890(17) -0.0019(4) 0.0245(9) Uani 1 1 d . . . C12 C 0.0910(3) 0.08116(17) -0.0149(4) 0.0227(8) Uani 1 1 d . . . C13 C -0.2254(3) 0.12235(17) 0.0902(4) 0.0255(8) Uani 1 1 d . . . C14 C -0.2692(3) 0.19164(19) 0.0700(5) 0.0358(10) Uani 1 1 d . . . H14A H -0.2196 0.2201 0.1286 0.054 Uiso 1 1 calc R . . H14B H -0.3497 0.1947 0.0966 0.054 Uiso 1 1 calc R . . H14C H -0.2660 0.2038 -0.0279 0.054 Uiso 1 1 calc R . . C15 C -0.3007(3) 0.07858(17) -0.0121(4) 0.0299(9) Uani 1 1 d . . . H15A H -0.2990 0.0950 -0.1071 0.045 Uiso 1 1 calc R . . H15B H -0.3812 0.0779 0.0150 0.045 Uiso 1 1 calc R . . H15C H -0.2689 0.0355 -0.0081 0.045 Uiso 1 1 calc R . . C16 C -0.2294(3) 0.1045(2) 0.2475(4) 0.0369(9) Uani 1 1 d . . . H16A H -0.1909 0.0635 0.2647 0.055 Uiso 1 1 calc R . . H16B H -0.3107 0.1016 0.2712 0.055 Uiso 1 1 calc R . . H16C H -0.1892 0.1371 0.3050 0.055 Uiso 1 1 calc R . . C17 C 0.2480(3) 0.16039(18) -0.0679(4) 0.0244(8) Uani 1 1 d . . . C18 C 0.2577(3) 0.23322(18) -0.0380(4) 0.0310(9) Uani 1 1 d . . . H18A H 0.1921 0.2552 -0.0872 0.046 Uiso 1 1 calc R . . H18B H 0.3310 0.2493 -0.0703 0.046 Uiso 1 1 calc R . . H18C H 0.2561 0.2407 0.0623 0.046 Uiso 1 1 calc R . . C19 C 0.2444(3) 0.14980(18) -0.2298(4) 0.0284(9) Uani 1 1 d . . . H19A H 0.2309 0.1048 -0.2506 0.043 Uiso 1 1 calc R . . H19B H 0.3188 0.1629 -0.2644 0.043 Uiso 1 1 calc R . . H19C H 0.1812 0.1751 -0.2752 0.043 Uiso 1 1 calc R . . C20 C 0.3514(3) 0.12675(18) 0.0144(4) 0.0329(9) Uani 1 1 d . . . H20A H 0.3578 0.1423 0.1106 0.049 Uiso 1 1 calc R . . H20B H 0.4238 0.1358 -0.0297 0.049 Uiso 1 1 calc R . . H20C H 0.3378 0.0809 0.0144 0.049 Uiso 1 1 calc R . . C21 C 0.5382(4) -0.0909(2) 0.0369(5) 0.0495(12) Uani 1 1 d . . . H21A H 0.5445 -0.0681 -0.0510 0.074 Uiso 1 1 calc R . . H21B H 0.4754 -0.1222 0.0256 0.074 Uiso 1 1 calc R . . H21C H 0.6119 -0.1125 0.0628 0.074 Uiso 1 1 calc R . . C22 C 0.5123(3) -0.0454(2) 0.1473(4) 0.0351(9) Uani 1 1 d . . . N1 N -0.0983(2) 0.12164(14) 0.0513(3) 0.0223(7) Uani 1 1 d . . . N2 N 0.1290(2) 0.13881(14) -0.0187(3) 0.0205(7) Uani 1 1 d . . . N3 N 0.4931(4) -0.0087(2) 0.2336(4) 0.0559(11) Uani 1 1 d . . . Cl2 Cl -0.05807(9) 0.26344(5) -0.16595(10) 0.0352(3) Uani 1 1 d . . . Cl1 Cl 0.03280(8) 0.25748(5) 0.23145(10) 0.0313(2) Uani 1 1 d . . . Zn1 Zn -0.00050(3) 0.205919(15) 0.02608(4) 0.02416(11) 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 C1 0.0213(19) 0.0185(17) 0.0251(19) -0.0002(16) 0.0002(16) -0.0040(14) C2 0.0189(17) 0.024(2) 0.024(2) 0.0017(17) -0.0012(15) -0.0001(16) C3 0.0298(19) 0.030(2) 0.036(2) 0.0044(17) 0.0025(18) -0.0012(17) C4 0.033(2) 0.028(2) 0.041(3) 0.0073(19) -0.0006(19) -0.0082(18) C5 0.036(2) 0.0196(17) 0.038(3) 0.0036(18) -0.0137(19) -0.0027(17) C6 0.0277(19) 0.024(2) 0.028(2) -0.0005(17) -0.0081(17) 0.0030(17) C7 0.037(2) 0.0189(19) 0.035(2) -0.0047(17) -0.0030(19) 0.0028(17) C8 0.038(2) 0.036(2) 0.032(2) -0.0070(18) 0.0033(18) 0.0103(19) C9 0.0274(18) 0.030(2) 0.034(2) -0.0015(17) 0.0059(17) 0.0026(17) C10 0.0234(18) 0.0213(19) 0.026(2) 0.0015(16) 0.0012(16) 0.0048(15) C11 0.0240(19) 0.023(2) 0.026(2) 0.0012(17) -0.0033(16) -0.0002(16) C12 0.0199(18) 0.026(2) 0.0215(19) 0.0008(16) 0.0003(15) 0.0014(16) C13 0.0195(17) 0.028(2) 0.029(2) 0.0012(17) 0.0054(15) 0.0025(15) C14 0.024(2) 0.038(3) 0.046(3) -0.007(2) 0.0049(18) 0.0058(19) C15 0.0235(18) 0.034(2) 0.032(2) 0.0020(17) 0.0035(16) -0.0019(16) C16 0.031(2) 0.052(3) 0.028(2) -0.006(2) 0.0045(17) 0.0018(19) C17 0.0187(17) 0.028(2) 0.027(2) 0.0013(17) 0.0047(15) -0.0033(15) C18 0.0250(19) 0.030(2) 0.039(3) -0.0018(19) 0.0061(17) -0.0092(17) C19 0.0260(19) 0.030(2) 0.029(2) 0.0015(17) 0.0023(17) -0.0041(16) C20 0.0236(18) 0.043(2) 0.032(2) -0.0047(18) 0.0033(16) -0.0033(17) C21 0.057(3) 0.044(2) 0.047(3) -0.006(2) 0.008(3) 0.004(2) C22 0.029(2) 0.038(2) 0.037(2) 0.011(2) 0.0017(19) -0.0045(18) N1 0.0170(15) 0.0284(17) 0.0222(17) -0.0035(15) 0.0055(13) -0.0007(14) N2 0.0176(15) 0.0239(18) 0.0200(16) 0.0012(13) 0.0013(12) -0.0015(12) N3 0.056(2) 0.059(3) 0.053(3) -0.002(3) 0.008(2) 0.000(2) Cl2 0.0450(6) 0.0298(6) 0.0297(6) 0.0047(4) -0.0050(5) 0.0033(4) Cl1 0.0323(5) 0.0339(6) 0.0273(6) -0.0052(5) -0.0009(4) 0.0055(4) Zn1 0.02538(19) 0.02001(19) 0.0271(2) -0.0001(2) 0.00170(14) 0.0008(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N1 1.278(4) . ? C1 C2 1.496(5) . ? C1 C12 1.549(5) . ? C2 C3 1.365(5) . ? C2 C11 1.414(4) . ? C3 C4 1.424(5) . ? C3 H3 0.9300 . ? C4 C5 1.363(5) . ? C4 H4 0.9300 . ? C5 C6 1.408(5) . ? C5 H5 0.9300 . ? C6 C7 1.409(5) . ? C6 C11 1.414(5) . ? C7 C8 1.360(5) . ? C7 H7 0.9300 . ? C8 C9 1.418(5) . ? C8 H8 0.9300 . ? C9 C10 1.388(5) . ? C9 H9 0.9300 . ? C10 C11 1.417(5) . ? C10 C12 1.477(5) . ? C12 N2 1.267(4) . ? C13 N1 1.504(4) . ? C13 C14 1.522(5) . ? C13 C16 1.532(5) . ? C13 C15 1.534(5) . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 0.9600 . ? C15 H15A 0.9600 . ? C15 H15B 0.9600 . ? C15 H15C 0.9600 . ? C16 H16A 0.9600 . ? C16 H16B 0.9600 . ? C16 H16C 0.9600 . ? C17 N2 1.517(4) . ? C17 C20 1.523(5) . ? C17 C18 1.533(5) . ? C17 C19 1.540(5) . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 0.9600 . ? C20 H20A 0.9600 . ? C20 H20B 0.9600 . ? C20 H20C 0.9600 . ? C21 C22 1.446(6) . ? C21 H21A 0.9600 . ? C21 H21B 0.9600 . ? C21 H21C 0.9600 . ? C22 N3 1.144(5) . ? N1 Zn1 2.083(3) . ? N2 Zn1 2.078(3) . ? Cl2 Zn1 2.2248(13) . ? Cl1 Zn1 2.2193(14) . ? 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 N1 C1 C2 137.0(3) . . ? N1 C1 C12 117.0(3) . . ? C2 C1 C12 105.9(3) . . ? C3 C2 C11 118.7(3) . . ? C3 C2 C1 135.3(3) . . ? C11 C2 C1 105.9(3) . . ? C2 C3 C4 119.4(3) . . ? C2 C3 H3 120.3 . . ? C4 C3 H3 120.3 . . ? C5 C4 C3 121.4(4) . . ? C5 C4 H4 119.3 . . ? C3 C4 H4 119.3 . . ? C4 C5 C6 121.2(3) . . ? C4 C5 H5 119.4 . . ? C6 C5 H5 119.4 . . ? C5 C6 C7 126.9(3) . . ? C5 C6 C11 116.3(3) . . ? C7 C6 C11 116.8(3) . . ? C8 C7 C6 120.7(3) . . ? C8 C7 H7 119.6 . . ? C6 C7 H7 119.6 . . ? C7 C8 C9 122.3(3) . . ? C7 C8 H8 118.9 . . ? C9 C8 H8 118.9 . . ? C10 C9 C8 119.1(3) . . ? C10 C9 H9 120.4 . . ? C8 C9 H9 120.4 . . ? C9 C10 C11 118.0(3) . . ? C9 C10 C12 135.2(3) . . ? C11 C10 C12 106.8(3) . . ? C2 C11 C6 122.7(3) . . ? C2 C11 C10 114.4(3) . . ? C6 C11 C10 122.9(3) . . ? N2 C12 C10 137.3(3) . . ? N2 C12 C1 116.8(3) . . ? C10 C12 C1 105.9(3) . . ? N1 C13 C14 106.6(3) . . ? N1 C13 C16 109.0(3) . . ? C14 C13 C16 108.5(3) . . ? N1 C13 C15 109.6(3) . . ? C14 C13 C15 108.4(3) . . ? C16 C13 C15 114.5(3) . . ? C13 C14 H14A 109.5 . . ? C13 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C13 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C13 C15 H15A 109.5 . . ? C13 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C13 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C13 C16 H16A 109.5 . . ? C13 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C13 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? N2 C17 C20 111.8(3) . . ? N2 C17 C18 106.6(3) . . ? C20 C17 C18 108.2(3) . . ? N2 C17 C19 107.3(3) . . ? C20 C17 C19 114.0(3) . . ? C18 C17 C19 108.6(3) . . ? C17 C18 H18A 109.5 . . ? C17 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C17 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C17 C19 H19A 109.5 . . ? C17 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C17 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? 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 . . ? C22 C21 H21A 109.5 . . ? C22 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C22 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? N3 C22 C21 178.8(5) . . ? C1 N1 C13 125.7(3) . . ? C1 N1 Zn1 111.3(2) . . ? C13 N1 Zn1 122.7(2) . . ? C12 N2 C17 126.4(3) . . ? C12 N2 Zn1 112.1(2) . . ? C17 N2 Zn1 121.0(2) . . ? N2 Zn1 N1 81.42(11) . . ? N2 Zn1 Cl1 114.75(9) . . ? N1 Zn1 Cl1 111.12(9) . . ? N2 Zn1 Cl2 111.13(9) . . ? N1 Zn1 Cl2 114.35(9) . . ? Cl1 Zn1 Cl2 118.44(4) . . ? 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 _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 C1 C2 C3 -15.7(8) . . . . ? C12 C1 C2 C3 168.7(4) . . . . ? N1 C1 C2 C11 166.5(5) . . . . ? C12 C1 C2 C11 -9.0(4) . . . . ? C11 C2 C3 C4 -1.8(5) . . . . ? C1 C2 C3 C4 -179.3(4) . . . . ? C2 C3 C4 C5 -2.1(6) . . . . ? C3 C4 C5 C6 2.2(7) . . . . ? C4 C5 C6 C7 178.7(4) . . . . ? C4 C5 C6 C11 1.6(6) . . . . ? C5 C6 C7 C8 -175.8(4) . . . . ? C11 C6 C7 C8 1.4(6) . . . . ? C6 C7 C8 C9 0.9(6) . . . . ? C7 C8 C9 C10 -1.1(6) . . . . ? C8 C9 C10 C11 -0.9(5) . . . . ? C8 C9 C10 C12 179.6(4) . . . . ? C3 C2 C11 C6 5.8(5) . . . . ? C1 C2 C11 C6 -176.1(4) . . . . ? C3 C2 C11 C10 -173.8(4) . . . . ? C1 C2 C11 C10 4.4(4) . . . . ? C5 C6 C11 C2 -5.6(5) . . . . ? C7 C6 C11 C2 177.0(3) . . . . ? C5 C6 C11 C10 173.9(4) . . . . ? C7 C6 C11 C10 -3.5(6) . . . . ? C9 C10 C11 C2 -177.1(3) . . . . ? C12 C10 C11 C2 2.5(4) . . . . ? C9 C10 C11 C6 3.3(5) . . . . ? C12 C10 C11 C6 -177.1(3) . . . . ? C9 C10 C12 N2 -8.1(7) . . . . ? C11 C10 C12 N2 172.4(4) . . . . ? C9 C10 C12 C1 171.5(4) . . . . ? C11 C10 C12 C1 -8.0(4) . . . . ? N1 C1 C12 N2 13.6(5) . . . . ? C2 C1 C12 N2 -169.8(3) . . . . ? N1 C1 C12 C10 -166.1(3) . . . . ? C2 C1 C12 C10 10.6(4) . . . . ? C2 C1 N1 C13 -1.0(7) . . . . ? C12 C1 N1 C13 174.3(3) . . . . ? C2 C1 N1 Zn1 173.7(4) . . . . ? C12 C1 N1 Zn1 -11.1(4) . . . . ? C14 C13 N1 C1 -172.6(4) . . . . ? C16 C13 N1 C1 70.5(4) . . . . ? C15 C13 N1 C1 -55.5(5) . . . . ? C14 C13 N1 Zn1 13.3(4) . . . . ? C16 C13 N1 Zn1 -103.6(3) . . . . ? C15 C13 N1 Zn1 130.4(3) . . . . ? C10 C12 N2 C17 -0.8(7) . . . . ? C1 C12 N2 C17 179.6(3) . . . . ? C10 C12 N2 Zn1 171.5(4) . . . . ? C1 C12 N2 Zn1 -8.0(4) . . . . ? C20 C17 N2 C12 -56.2(5) . . . . ? C18 C17 N2 C12 -174.3(3) . . . . ? C19 C17 N2 C12 69.6(4) . . . . ? C20 C17 N2 Zn1 132.1(3) . . . . ? C18 C17 N2 Zn1 14.0(4) . . . . ? C19 C17 N2 Zn1 -102.1(3) . . . . ? C12 N2 Zn1 N1 1.9(3) . . . . ? C17 N2 Zn1 N1 174.7(3) . . . . ? C12 N2 Zn1 Cl1 111.3(2) . . . . ? C17 N2 Zn1 Cl1 -75.9(3) . . . . ? C12 N2 Zn1 Cl2 -110.9(2) . . . . ? C17 N2 Zn1 Cl2 61.9(3) . . . . ? C1 N1 Zn1 N2 5.5(3) . . . . ? C13 N1 Zn1 N2 -179.6(3) . . . . ? C1 N1 Zn1 Cl1 -107.8(3) . . . . ? C13 N1 Zn1 Cl1 67.1(3) . . . . ? C1 N1 Zn1 Cl2 114.9(3) . . . . ? C13 N1 Zn1 Cl2 -70.3(3) . . . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.574 _refine_diff_density_min -0.533 _refine_diff_density_rms 0.077 data_CF3C6H4-BIAN _database_code_depnum_ccdc_archive 'CCDC 606233' _audit_creation_method ; manual editing of the .cif file created by SHELXTL Ver. 6.10 ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C26 H14 F6 N2 ' _chemical_formula_sum 'C26 H14 F6 N2' _chemical_formula_weight 468.39 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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M p21/c _symmetry_space_group_name_Hall -p2ybc 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 21.339(5) _cell_length_b 11.819(5) _cell_length_c 16.806(5) _cell_angle_alpha 90.000 _cell_angle_beta 90.076(5) _cell_angle_gamma 90.000 _cell_volume 4239(2) _cell_formula_units_Z 8 _cell_measurement_temperature 153(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour orange _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.468 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1904 _exptl_absorpt_coefficient_mu 0.124 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.971 _exptl_absorpt_correction_T_max 0.976 _exptl_absorpt_process_details 'DENZO and Scalepack (Otwinoski and Minor, 1997)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 153(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method \w-scan _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 21062 _diffrn_reflns_av_R_equivalents 0.0579 _diffrn_reflns_av_sigmaI/netI 0.0971 _diffrn_reflns_limit_h_min -26 _diffrn_reflns_limit_h_max 27 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.11 _diffrn_reflns_theta_max 27.48 _reflns_number_total 9114 _reflns_number_gt 4812 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect software, Nonius B.V. 1998' _computing_cell_refinement 'Collect software, Nonius B.V. 1998' _computing_data_reduction ; DENZO and Scalepack (Otwinoski and Minor, 1997) ; _computing_structure_solution ; SIR97 - Altomare A., Burla M.C., Camalli M., Cascarano G.L., Giacovazzo C., Guagliardi A., Moliterni A.G.G., Polidori G.,Spagna R. ; _computing_structure_refinement 'XL SHELXTL/PC, Siemens Analytical' _computing_molecular_graphics 'XP SHELXTL/PC, Siemens Analytical' _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^)+(0.0814P)^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 9114 _refine_ls_number_parameters 613 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1372 _refine_ls_R_factor_gt 0.0597 _refine_ls_wR_factor_ref 0.1691 _refine_ls_wR_factor_gt 0.1347 _refine_ls_goodness_of_fit_ref 1.009 _refine_ls_restrained_S_all 1.009 _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 C1 C 0.62729(12) -0.0629(2) 0.42145(16) 0.0350(6) Uani 1 1 d . . . C2 C 0.62329(12) -0.0752(2) 0.33414(16) 0.0361(6) Uani 1 1 d . . . C3 C 0.62960(13) -0.1641(2) 0.28163(17) 0.0451(7) Uani 1 1 d . . . H3 H 0.6398 -0.2360 0.3001 0.054 Uiso 1 1 calc R . . C4 C 0.62041(14) -0.1450(2) 0.20016(18) 0.0493(7) Uani 1 1 d . . . H4 H 0.6238 -0.2056 0.1651 0.059 Uiso 1 1 calc R . . C5 C 0.60652(14) -0.0396(2) 0.17042(17) 0.0487(8) Uani 1 1 d . . . H5 H 0.6011 -0.0300 0.1159 0.058 Uiso 1 1 calc R . . C6 C 0.60036(13) 0.0538(2) 0.22144(16) 0.0404(7) Uani 1 1 d . . . C7 C 0.58573(14) 0.1675(2) 0.20093(19) 0.0502(8) Uani 1 1 d . . . H7 H 0.5800 0.1871 0.1478 0.060 Uiso 1 1 calc R . . C8 C 0.58003(15) 0.2480(2) 0.25886(19) 0.0537(8) Uani 1 1 d . . . H8 H 0.5705 0.3217 0.2437 0.064 Uiso 1 1 calc R . . C9 C 0.58788(14) 0.2245(2) 0.34059(18) 0.0485(7) Uani 1 1 d . . . H9 H 0.5833 0.2811 0.3786 0.058 Uiso 1 1 calc R . . C10 C 0.60241(12) 0.1162(2) 0.36217(16) 0.0372(6) Uani 1 1 d . . . C11 C 0.60829(12) 0.0325(2) 0.30285(16) 0.0360(6) Uani 1 1 d . . . C12 C 0.61288(12) 0.0607(2) 0.43953(16) 0.0355(6) Uani 1 1 d . . . C13 C 0.65401(13) -0.2481(2) 0.45923(16) 0.0412(7) Uani 1 1 d . . . C14 C 0.60814(14) -0.3309(2) 0.46195(16) 0.0418(7) Uani 1 1 d . . . C15 C 0.62339(16) -0.4439(2) 0.45100(17) 0.0514(8) Uani 1 1 d . . . H15 H 0.5922 -0.4987 0.4525 0.062 Uiso 1 1 calc R . . C16 C 0.68442(18) -0.4750(3) 0.43791(19) 0.0615(9) Uani 1 1 d . . . H16 H 0.6947 -0.5508 0.4312 0.074 Uiso 1 1 calc R . . C17 C 0.73063(17) -0.3931(3) 0.43479(19) 0.0611(9) Uani 1 1 d . . . H17 H 0.7719 -0.4144 0.4251 0.073 Uiso 1 1 calc R . . C18 C 0.71660(14) -0.2815(3) 0.44571(17) 0.0517(8) Uani 1 1 d . . . H18 H 0.7483 -0.2275 0.4442 0.062 Uiso 1 1 calc R . . C19 C 0.54134(14) -0.2981(2) 0.47622(18) 0.0441(7) Uani 1 1 d . . . C20 C 0.61450(12) 0.0555(2) 0.58039(16) 0.0361(6) Uani 1 1 d . . . C21 C 0.66956(13) 0.0673(2) 0.62500(17) 0.0413(7) Uani 1 1 d . . . C22 C 0.67269(15) 0.0184(2) 0.70023(19) 0.0526(8) Uani 1 1 d . . . H22 H 0.7093 0.0246 0.7300 0.063 Uiso 1 1 calc R . . C23 C 0.62222(16) -0.0389(2) 0.73094(18) 0.0519(8) Uani 1 1 d . . . H23 H 0.6248 -0.0713 0.7813 0.062 Uiso 1 1 calc R . . C24 C 0.56780(15) -0.0485(2) 0.68729(18) 0.0479(8) Uani 1 1 d . . . H24 H 0.5336 -0.0867 0.7084 0.057 Uiso 1 1 calc R . . C25 C 0.56397(13) -0.0017(2) 0.61271(17) 0.0395(7) Uani 1 1 d . . . H25 H 0.5271 -0.0085 0.5836 0.047 Uiso 1 1 calc R . . C26 C 0.72457(16) 0.1290(3) 0.5916(2) 0.0633(9) Uani 1 1 d . . . C27 C 0.97399(11) -0.29612(18) 0.56314(15) 0.0294(6) Uani 1 1 d . . . C28 C 0.96198(11) -0.32281(18) 0.47882(15) 0.0302(6) Uani 1 1 d . . . C29 C 0.92326(12) -0.39608(19) 0.43833(16) 0.0345(6) Uani 1 1 d . . . H29 H 0.8972 -0.4453 0.4660 0.041 Uiso 1 1 calc R . . C30 C 0.92360(12) -0.3956(2) 0.35455(16) 0.0388(7) Uani 1 1 d . . . H30 H 0.8975 -0.4457 0.3277 0.047 Uiso 1 1 calc R . . C31 C 0.96100(12) -0.3242(2) 0.31087(16) 0.0363(6) Uani 1 1 d . . . H31 H 0.9597 -0.3261 0.2556 0.044 Uiso 1 1 calc R . . C32 C 1.00168(11) -0.24745(19) 0.35040(15) 0.0321(6) Uani 1 1 d . . . C33 C 1.04299(12) -0.1680(2) 0.31392(16) 0.0373(6) Uani 1 1 d . . . H33 H 1.0443 -0.1618 0.2588 0.045 Uiso 1 1 calc R . . C34 C 1.08078(12) -0.1009(2) 0.36014(16) 0.0364(6) Uani 1 1 d . . . H34 H 1.1072 -0.0493 0.3353 0.044 Uiso 1 1 calc R . . C35 C 1.08095(12) -0.10716(19) 0.44382(16) 0.0347(6) Uani 1 1 d . . . H35 H 1.1076 -0.0614 0.4735 0.042 Uiso 1 1 calc R . . C36 C 1.04120(11) -0.18191(19) 0.48115(15) 0.0312(6) Uani 1 1 d . . . C37 C 1.00165(11) -0.25046(18) 0.43359(14) 0.0289(6) Uani 1 1 d . . . C38 C 1.02966(11) -0.21564(19) 0.56460(15) 0.0304(6) Uani 1 1 d . . . C39 C 0.89168(12) -0.39098(19) 0.62503(14) 0.0311(6) Uani 1 1 d . . . C40 C 0.83079(12) -0.34699(19) 0.62603(15) 0.0330(6) Uani 1 1 d . . . C41 C 0.77990(13) -0.4201(2) 0.62737(17) 0.0430(7) Uani 1 1 d . . . H41 H 0.7395 -0.3907 0.6274 0.052 Uiso 1 1 calc R . . C42 C 0.78854(14) -0.5358(2) 0.62864(18) 0.0489(8) Uani 1 1 d . . . H42 H 0.7541 -0.5841 0.6289 0.059 Uiso 1 1 calc R . . C43 C 0.84866(14) -0.5795(2) 0.62947(17) 0.0469(7) Uani 1 1 d . . . H43 H 0.8546 -0.6574 0.6310 0.056 Uiso 1 1 calc R . . C44 C 0.89967(13) -0.5084(2) 0.62803(16) 0.0395(7) Uani 1 1 d . . . H44 H 0.9399 -0.5387 0.6291 0.047 Uiso 1 1 calc R . . C45 C 0.82009(13) -0.2222(2) 0.62570(19) 0.0460(7) Uani 1 1 d . . . C46 C 1.10798(12) -0.11834(19) 0.63535(15) 0.0323(6) Uani 1 1 d . . . C47 C 1.16987(12) -0.1548(2) 0.64377(15) 0.0337(6) Uani 1 1 d . . . C48 C 1.21713(13) -0.0770(2) 0.65819(16) 0.0431(7) Uani 1 1 d . . . H48 H 1.2583 -0.1016 0.6639 0.052 Uiso 1 1 calc R . . C49 C 1.20331(14) 0.0372(2) 0.66411(17) 0.0487(8) Uani 1 1 d . . . H49 H 1.2350 0.0893 0.6743 0.058 Uiso 1 1 calc R . . C50 C 1.14260(14) 0.0729(2) 0.65487(18) 0.0486(8) Uani 1 1 d . . . H50 H 1.1333 0.1497 0.6584 0.058 Uiso 1 1 calc R . . C51 C 1.09535(13) -0.0032(2) 0.64043(16) 0.0414(7) Uani 1 1 d . . . H51 H 1.0545 0.0225 0.6340 0.050 Uiso 1 1 calc R . . C52 C 1.18588(13) -0.2779(2) 0.63767(19) 0.0451(7) Uani 1 1 d . . . N1 N 0.64002(10) -0.13309(16) 0.47692(13) 0.0387(5) Uani 1 1 d . . . N2 N 0.60805(10) 0.11176(16) 0.50613(14) 0.0392(5) Uani 1 1 d . . . N3 N 0.94474(9) -0.31940(16) 0.62737(12) 0.0327(5) Uani 1 1 d . . . N4 N 1.05764(9) -0.19592(16) 0.63009(13) 0.0331(5) Uani 1 1 d . . . F1 F 0.53295(8) -0.24933(16) 0.54762(11) 0.0694(5) Uani 1 1 d . . . F2 F 0.50182(9) -0.38549(13) 0.47432(12) 0.0715(6) Uani 1 1 d . . . F3 F 0.51978(8) -0.22352(13) 0.42315(11) 0.0607(5) Uani 1 1 d . . . F4 F 0.77108(9) 0.1407(2) 0.64282(14) 0.1031(8) Uani 1 1 d . . . F5 F 0.70983(10) 0.23449(17) 0.56778(13) 0.0885(7) Uani 1 1 d . . . F6 F 0.74838(9) 0.07761(19) 0.52755(13) 0.0858(6) Uani 1 1 d . . . F7 F 0.75926(8) -0.19478(13) 0.62477(11) 0.0613(5) Uani 1 1 d . . . F8 F 0.84419(9) -0.17127(13) 0.69028(12) 0.0669(5) Uani 1 1 d . . . F9 F 0.84580(8) -0.16986(13) 0.56295(12) 0.0634(5) Uani 1 1 d . . . F10 F 1.16818(9) -0.32371(13) 0.56836(11) 0.0668(5) Uani 1 1 d . . . F11 F 1.15889(8) -0.34125(13) 0.69393(11) 0.0642(5) Uani 1 1 d . . . F12 F 1.24738(8) -0.29704(14) 0.64410(12) 0.0701(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 C1 0.0334(14) 0.0367(14) 0.0349(16) 0.0019(12) -0.0038(12) -0.0041(11) C2 0.0359(15) 0.0371(14) 0.0354(17) 0.0024(12) -0.0019(12) -0.0006(12) C3 0.0520(18) 0.0445(15) 0.0389(19) -0.0005(13) -0.0011(14) 0.0018(13) C4 0.0577(19) 0.0511(17) 0.0391(19) -0.0051(14) -0.0011(15) 0.0006(15) C5 0.0536(19) 0.0626(19) 0.0299(17) 0.0029(14) 0.0000(14) -0.0043(15) C6 0.0398(16) 0.0475(16) 0.0338(17) 0.0060(13) 0.0001(13) -0.0061(13) C7 0.0569(19) 0.0527(18) 0.0409(19) 0.0131(15) -0.0016(15) -0.0095(15) C8 0.066(2) 0.0394(16) 0.055(2) 0.0186(15) -0.0016(16) -0.0057(14) C9 0.0581(19) 0.0362(15) 0.051(2) 0.0043(14) -0.0004(15) -0.0074(13) C10 0.0362(15) 0.0375(15) 0.0379(17) 0.0035(12) -0.0006(13) -0.0057(12) C11 0.0297(14) 0.0396(15) 0.0387(17) 0.0036(12) -0.0017(12) -0.0064(11) C12 0.0332(15) 0.0361(14) 0.0373(17) 0.0002(13) -0.0031(12) -0.0056(11) C13 0.0557(19) 0.0388(15) 0.0291(16) 0.0031(12) -0.0037(13) 0.0054(14) C14 0.0540(18) 0.0386(15) 0.0328(17) 0.0033(12) -0.0027(14) 0.0056(13) C15 0.074(2) 0.0402(16) 0.0402(19) 0.0008(13) -0.0007(16) 0.0073(15) C16 0.088(3) 0.0492(18) 0.047(2) -0.0022(15) -0.0006(18) 0.022(2) C17 0.067(2) 0.068(2) 0.049(2) -0.0005(16) 0.0000(17) 0.0334(19) C18 0.0508(19) 0.0615(19) 0.0428(19) 0.0047(15) -0.0086(15) 0.0122(15) C19 0.0581(19) 0.0303(14) 0.0439(19) 0.0024(13) -0.0052(15) -0.0060(13) C20 0.0429(16) 0.0309(13) 0.0345(16) -0.0060(12) -0.0020(13) 0.0032(12) C21 0.0412(16) 0.0410(15) 0.0417(18) -0.0108(13) -0.0046(14) 0.0009(12) C22 0.058(2) 0.0537(17) 0.046(2) -0.0081(15) -0.0131(16) 0.0130(16) C23 0.076(2) 0.0415(16) 0.0380(18) 0.0022(13) -0.0067(17) 0.0127(16) C24 0.058(2) 0.0371(15) 0.048(2) -0.0012(14) 0.0080(16) -0.0005(14) C25 0.0412(16) 0.0366(14) 0.0407(18) 0.0005(13) -0.0025(13) -0.0032(12) C26 0.054(2) 0.080(2) 0.056(2) -0.0134(19) -0.0018(18) -0.0155(18) C27 0.0312(14) 0.0297(12) 0.0274(15) -0.0003(11) -0.0029(11) 0.0011(11) C28 0.0311(14) 0.0297(13) 0.0298(15) 0.0014(11) -0.0008(11) -0.0004(11) C29 0.0361(15) 0.0333(13) 0.0340(17) 0.0001(11) -0.0007(12) -0.0025(11) C30 0.0418(16) 0.0397(14) 0.0348(17) -0.0056(12) -0.0078(13) -0.0062(12) C31 0.0434(16) 0.0400(14) 0.0257(15) -0.0011(12) -0.0031(12) -0.0001(12) C32 0.0349(15) 0.0315(13) 0.0299(16) 0.0011(11) 0.0009(12) 0.0041(11) C33 0.0419(16) 0.0406(14) 0.0294(16) 0.0004(12) 0.0037(13) 0.0035(13) C34 0.0376(15) 0.0334(14) 0.0383(18) 0.0057(12) 0.0060(13) -0.0015(11) C35 0.0364(15) 0.0320(13) 0.0356(17) -0.0010(11) 0.0019(12) -0.0038(11) C36 0.0313(14) 0.0310(13) 0.0313(15) -0.0010(11) 0.0023(12) 0.0018(11) C37 0.0320(14) 0.0276(12) 0.0271(15) -0.0004(10) 0.0003(11) 0.0024(11) C38 0.0316(14) 0.0309(13) 0.0287(16) -0.0043(11) 0.0024(12) 0.0012(11) C39 0.0360(15) 0.0350(14) 0.0223(14) 0.0010(10) -0.0007(11) -0.0048(11) C40 0.0379(15) 0.0333(13) 0.0278(15) 0.0002(11) -0.0016(12) -0.0018(12) C41 0.0358(16) 0.0485(17) 0.0448(18) -0.0009(13) 0.0012(13) -0.0040(13) C42 0.0492(19) 0.0463(17) 0.051(2) -0.0007(14) 0.0025(15) -0.0177(14) C43 0.063(2) 0.0291(13) 0.0485(19) 0.0028(12) -0.0015(15) -0.0067(14) C44 0.0425(16) 0.0338(14) 0.0421(17) 0.0033(12) 0.0022(13) 0.0022(12) C45 0.0398(17) 0.0421(16) 0.056(2) -0.0031(15) -0.0062(15) 0.0022(13) C46 0.0338(15) 0.0368(14) 0.0262(15) -0.0021(11) 0.0003(11) -0.0019(11) C47 0.0355(15) 0.0370(14) 0.0287(15) -0.0034(11) 0.0028(12) -0.0024(12) C48 0.0323(15) 0.0537(17) 0.0432(18) -0.0010(14) -0.0008(13) -0.0050(13) C49 0.0489(19) 0.0476(17) 0.050(2) -0.0052(14) -0.0071(15) -0.0175(14) C50 0.0519(19) 0.0365(15) 0.057(2) -0.0070(14) -0.0027(16) -0.0039(14) C51 0.0384(16) 0.0374(15) 0.0484(18) -0.0043(13) -0.0022(14) 0.0030(12) C52 0.0387(17) 0.0462(16) 0.050(2) -0.0012(15) 0.0048(14) 0.0029(13) N1 0.0421(13) 0.0359(12) 0.0380(14) 0.0018(10) -0.0043(11) 0.0023(10) N2 0.0434(14) 0.0360(12) 0.0383(15) 0.0024(11) -0.0024(11) -0.0062(10) N3 0.0336(12) 0.0333(11) 0.0312(13) 0.0017(9) 0.0000(10) -0.0038(9) N4 0.0314(12) 0.0354(11) 0.0324(13) -0.0010(9) -0.0002(10) -0.0032(9) F1 0.0616(12) 0.0844(13) 0.0625(13) -0.0159(10) 0.0115(10) 0.0075(9) F2 0.0687(12) 0.0489(10) 0.0970(16) 0.0080(9) -0.0027(11) -0.0165(9) F3 0.0497(10) 0.0530(9) 0.0793(13) 0.0170(9) -0.0090(9) -0.0013(8) F4 0.0518(13) 0.174(2) 0.0838(17) -0.0168(15) -0.0186(12) -0.0351(13) F5 0.0861(15) 0.0712(13) 0.1082(18) 0.0003(12) 0.0032(13) -0.0420(12) F6 0.0633(13) 0.1175(16) 0.0767(15) -0.0232(13) 0.0228(11) -0.0169(12) F7 0.0454(10) 0.0508(10) 0.0876(14) -0.0085(9) -0.0082(9) 0.0119(8) F8 0.0731(12) 0.0471(9) 0.0804(14) -0.0255(9) -0.0260(11) 0.0082(8) F9 0.0662(12) 0.0429(9) 0.0810(14) 0.0197(9) 0.0052(10) 0.0027(8) F10 0.0816(13) 0.0526(10) 0.0663(13) -0.0265(9) -0.0045(10) 0.0093(9) F11 0.0696(12) 0.0466(9) 0.0765(14) 0.0163(9) 0.0154(10) 0.0060(9) F12 0.0408(11) 0.0625(11) 0.1069(16) -0.0079(10) 0.0027(10) 0.0155(8) _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 C1 N1 1.277(3) . ? C1 C2 1.477(4) . ? C1 C12 1.524(4) . ? C2 C3 1.379(4) . ? C2 C11 1.414(3) . ? C3 C4 1.401(4) . ? C3 H3 0.9300 . ? C4 C5 1.375(4) . ? C4 H4 0.9300 . ? C5 C6 1.404(4) . ? C5 H5 0.9300 . ? C6 C11 1.401(4) . ? C6 C7 1.422(4) . ? C7 C8 1.368(4) . ? C7 H7 0.9300 . ? C8 C9 1.411(4) . ? C8 H8 0.9300 . ? C9 C10 1.367(4) . ? C9 H9 0.9300 . ? C10 C11 1.410(4) . ? C10 C12 1.473(4) . ? C12 N2 1.276(3) . ? C13 C14 1.385(4) . ? C13 C18 1.411(4) . ? C13 N1 1.423(3) . ? C14 C15 1.386(4) . ? C14 C19 1.497(4) . ? C15 C16 1.371(4) . ? C15 H15 0.9300 . ? C16 C17 1.382(5) . ? C16 H16 0.9300 . ? C17 C18 1.366(4) . ? C17 H17 0.9300 . ? C18 H18 0.9300 . ? C19 F3 1.335(3) . ? C19 F2 1.334(3) . ? C19 F1 1.343(3) . ? C20 C25 1.384(4) . ? C20 C21 1.400(4) . ? C20 N2 1.420(3) . ? C21 C22 1.391(4) . ? C21 C26 1.492(4) . ? C22 C23 1.374(4) . ? C22 H22 0.9300 . ? C23 C24 1.377(4) . ? C23 H23 0.9300 . ? C24 C25 1.372(4) . ? C24 H24 0.9300 . ? C25 H25 0.9300 . ? C26 F4 1.320(4) . ? C26 F6 1.337(4) . ? C26 F5 1.347(4) . ? C27 N3 1.278(3) . ? C27 C28 1.474(3) . ? C27 C38 1.522(3) . ? C28 C29 1.376(3) . ? C28 C37 1.424(3) . ? C29 C30 1.408(4) . ? C29 H29 0.9300 . ? C30 C31 1.375(4) . ? C30 H30 0.9300 . ? C31 C32 1.420(3) . ? C31 H31 0.9300 . ? C32 C37 1.398(3) . ? C32 C33 1.427(4) . ? C33 C34 1.372(4) . ? C33 H33 0.9300 . ? C34 C35 1.408(4) . ? C34 H34 0.9300 . ? C35 C36 1.377(3) . ? C35 H35 0.9300 . ? C36 C37 1.416(3) . ? C36 C38 1.479(3) . ? C38 N4 1.273(3) . ? C39 C44 1.399(3) . ? C39 C40 1.400(3) . ? C39 N3 1.414(3) . ? C40 C41 1.388(3) . ? C40 C45 1.493(4) . ? C41 C42 1.380(4) . ? C41 H41 0.9300 . ? C42 C43 1.383(4) . ? C42 H42 0.9300 . ? C43 C44 1.375(4) . ? C43 H43 0.9300 . ? C44 H44 0.9300 . ? C45 F7 1.338(3) . ? C45 F9 1.341(3) . ? C45 F8 1.343(3) . ? C46 C51 1.390(3) . ? C46 C47 1.396(3) . ? C46 N4 1.415(3) . ? C47 C48 1.386(3) . ? C47 C52 1.498(4) . ? C48 C49 1.385(4) . ? C48 H48 0.9300 . ? C49 C50 1.371(4) . ? C49 H49 0.9300 . ? C50 C51 1.373(4) . ? C50 H50 0.9300 . ? C51 H51 0.9300 . ? C52 F12 1.336(3) . ? C52 F11 1.337(3) . ? C52 F10 1.338(3) . ? 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 N1 C1 C2 132.4(2) . . ? N1 C1 C12 121.3(2) . . ? C2 C1 C12 106.3(2) . . ? C3 C2 C11 118.1(2) . . ? C3 C2 C1 134.8(2) . . ? C11 C2 C1 107.1(2) . . ? C2 C3 C4 119.3(3) . . ? C2 C3 H3 120.4 . . ? C4 C3 H3 120.4 . . ? C5 C4 C3 122.1(3) . . ? C5 C4 H4 119.0 . . ? C3 C4 H4 119.0 . . ? C4 C5 C6 120.7(3) . . ? C4 C5 H5 119.6 . . ? C6 C5 H5 119.6 . . ? C11 C6 C5 116.4(2) . . ? C11 C6 C7 115.6(3) . . ? C5 C6 C7 128.0(3) . . ? C8 C7 C6 120.3(3) . . ? C8 C7 H7 119.8 . . ? C6 C7 H7 119.8 . . ? C7 C8 C9 123.1(3) . . ? C7 C8 H8 118.5 . . ? C9 C8 H8 118.5 . . ? C10 C9 C8 118.0(3) . . ? C10 C9 H9 121.0 . . ? C8 C9 H9 121.0 . . ? C9 C10 C11 119.3(3) . . ? C9 C10 C12 133.3(3) . . ? C11 C10 C12 107.4(2) . . ? C6 C11 C10 123.7(2) . . ? C6 C11 C2 123.5(2) . . ? C10 C11 C2 112.9(2) . . ? N2 C12 C10 123.4(2) . . ? N2 C12 C1 130.2(2) . . ? C10 C12 C1 106.4(2) . . ? C14 C13 C18 118.5(2) . . ? C14 C13 N1 121.3(2) . . ? C18 C13 N1 120.0(3) . . ? C13 C14 C15 120.7(3) . . ? C13 C14 C19 119.7(2) . . ? C15 C14 C19 119.7(3) . . ? C16 C15 C14 120.2(3) . . ? C16 C15 H15 119.9 . . ? C14 C15 H15 119.9 . . ? C15 C16 C17 119.8(3) . . ? C15 C16 H16 120.1 . . ? C17 C16 H16 120.1 . . ? C18 C17 C16 121.0(3) . . ? C18 C17 H17 119.5 . . ? C16 C17 H17 119.5 . . ? C17 C18 C13 120.0(3) . . ? C17 C18 H18 120.0 . . ? C13 C18 H18 120.0 . . ? F3 C19 F2 106.1(2) . . ? F3 C19 F1 105.5(2) . . ? F2 C19 F1 105.6(2) . . ? F3 C19 C14 113.0(2) . . ? F2 C19 C14 113.4(2) . . ? F1 C19 C14 112.5(2) . . ? C25 C20 C21 119.5(3) . . ? C25 C20 N2 119.9(2) . . ? C21 C20 N2 120.3(2) . . ? C22 C21 C20 119.0(3) . . ? C22 C21 C26 120.5(3) . . ? C20 C21 C26 120.5(3) . . ? C23 C22 C21 120.6(3) . . ? C23 C22 H22 119.7 . . ? C21 C22 H22 119.7 . . ? C22 C23 C24 120.1(3) . . ? C22 C23 H23 120.0 . . ? C24 C23 H23 120.0 . . ? C25 C24 C23 120.2(3) . . ? C25 C24 H24 119.9 . . ? C23 C24 H24 119.9 . . ? C24 C25 C20 120.7(3) . . ? C24 C25 H25 119.7 . . ? C20 C25 H25 119.7 . . ? F4 C26 F6 106.6(3) . . ? F4 C26 F5 105.8(3) . . ? F6 C26 F5 105.7(3) . . ? F4 C26 C21 113.4(3) . . ? F6 C26 C21 112.4(3) . . ? F5 C26 C21 112.4(3) . . ? N3 C27 C28 133.0(2) . . ? N3 C27 C38 120.2(2) . . ? C28 C27 C38 106.5(2) . . ? C29 C28 C37 118.1(2) . . ? C29 C28 C27 135.5(2) . . ? C37 C28 C27 106.4(2) . . ? C28 C29 C30 119.2(2) . . ? C28 C29 H29 120.4 . . ? C30 C29 H29 120.4 . . ? C31 C30 C29 122.7(2) . . ? C31 C30 H30 118.7 . . ? C29 C30 H30 118.7 . . ? C30 C31 C32 119.8(2) . . ? C30 C31 H31 120.1 . . ? C32 C31 H31 120.1 . . ? C37 C32 C31 116.8(2) . . ? C37 C32 C33 116.6(2) . . ? C31 C32 C33 126.6(2) . . ? C34 C33 C32 120.0(2) . . ? C34 C33 H33 120.0 . . ? C32 C33 H33 120.0 . . ? C33 C34 C35 122.4(2) . . ? C33 C34 H34 118.8 . . ? C35 C34 H34 118.8 . . ? C36 C35 C34 119.2(2) . . ? C36 C35 H35 120.4 . . ? C34 C35 H35 120.4 . . ? C35 C36 C37 118.5(2) . . ? C35 C36 C38 135.1(2) . . ? C37 C36 C38 106.3(2) . . ? C32 C37 C36 123.3(2) . . ? C32 C37 C28 123.4(2) . . ? C36 C37 C28 113.4(2) . . ? N4 C38 C36 133.8(2) . . ? N4 C38 C27 119.6(2) . . ? C36 C38 C27 106.5(2) . . ? C44 C39 C40 118.8(2) . . ? C44 C39 N3 119.7(2) . . ? C40 C39 N3 121.4(2) . . ? C41 C40 C39 119.7(2) . . ? C41 C40 C45 119.7(2) . . ? C39 C40 C45 120.6(2) . . ? C42 C41 C40 120.8(3) . . ? C42 C41 H41 119.6 . . ? C40 C41 H41 119.6 . . ? C41 C42 C43 119.6(2) . . ? C41 C42 H42 120.2 . . ? C43 C42 H42 120.2 . . ? C44 C43 C42 120.4(2) . . ? C44 C43 H43 119.8 . . ? C42 C43 H43 119.8 . . ? C43 C44 C39 120.7(2) . . ? C43 C44 H44 119.7 . . ? C39 C44 H44 119.7 . . ? F7 C45 F9 106.1(2) . . ? F7 C45 F8 105.8(2) . . ? F9 C45 F8 105.8(2) . . ? F7 C45 C40 112.8(2) . . ? F9 C45 C40 113.3(2) . . ? F8 C45 C40 112.4(2) . . ? C51 C46 C47 118.7(2) . . ? C51 C46 N4 119.4(2) . . ? C47 C46 N4 121.6(2) . . ? C48 C47 C46 120.1(2) . . ? C48 C47 C52 119.4(2) . . ? C46 C47 C52 120.6(2) . . ? C49 C48 C47 120.3(3) . . ? C49 C48 H48 119.9 . . ? C47 C48 H48 119.9 . . ? C50 C49 C48 119.5(2) . . ? C50 C49 H49 120.2 . . ? C48 C49 H49 120.2 . . ? C49 C50 C51 120.8(3) . . ? C49 C50 H50 119.6 . . ? C51 C50 H50 119.6 . . ? C50 C51 C46 120.7(3) . . ? C50 C51 H51 119.7 . . ? C46 C51 H51 119.7 . . ? F12 C52 F11 105.8(2) . . ? F12 C52 F10 106.1(2) . . ? F11 C52 F10 105.6(2) . . ? F12 C52 C47 112.5(2) . . ? F11 C52 C47 113.4(2) . . ? F10 C52 C47 112.8(2) . . ? C1 N1 C13 120.8(2) . . ? C12 N2 C20 122.8(2) . . ? C27 N3 C39 119.8(2) . . ? C38 N4 C46 121.9(2) . . ? 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 _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 C1 C2 C3 2.3(5) . . . . ? C12 C1 C2 C3 -178.1(3) . . . . ? N1 C1 C2 C11 -179.0(3) . . . . ? C12 C1 C2 C11 0.5(3) . . . . ? C11 C2 C3 C4 -0.6(4) . . . . ? C1 C2 C3 C4 177.9(3) . . . . ? C2 C3 C4 C5 1.4(4) . . . . ? C3 C4 C5 C6 -0.6(5) . . . . ? C4 C5 C6 C11 -0.8(4) . . . . ? C4 C5 C6 C7 -179.4(3) . . . . ? C11 C6 C7 C8 -0.2(4) . . . . ? C5 C6 C7 C8 178.4(3) . . . . ? C6 C7 C8 C9 -0.2(5) . . . . ? C7 C8 C9 C10 0.6(4) . . . . ? C8 C9 C10 C11 -0.7(4) . . . . ? C8 C9 C10 C12 -178.9(3) . . . . ? C5 C6 C11 C10 -178.7(2) . . . . ? C7 C6 C11 C10 0.1(4) . . . . ? C5 C6 C11 C2 1.6(4) . . . . ? C7 C6 C11 C2 -179.7(2) . . . . ? C9 C10 C11 C6 0.3(4) . . . . ? C12 C10 C11 C6 179.0(2) . . . . ? C9 C10 C11 C2 -179.9(2) . . . . ? C12 C10 C11 C2 -1.3(3) . . . . ? C3 C2 C11 C6 -0.9(4) . . . . ? C1 C2 C11 C6 -179.7(2) . . . . ? C3 C2 C11 C10 179.3(2) . . . . ? C1 C2 C11 C10 0.5(3) . . . . ? C9 C10 C12 N2 1.6(5) . . . . ? C11 C10 C12 N2 -176.7(2) . . . . ? C9 C10 C12 C1 179.8(3) . . . . ? C11 C10 C12 C1 1.5(3) . . . . ? N1 C1 C12 N2 -3.6(4) . . . . ? C2 C1 C12 N2 176.8(3) . . . . ? N1 C1 C12 C10 178.4(2) . . . . ? C2 C1 C12 C10 -1.2(3) . . . . ? C18 C13 C14 C15 -0.5(4) . . . . ? N1 C13 C14 C15 -174.7(3) . . . . ? C18 C13 C14 C19 180.0(2) . . . . ? N1 C13 C14 C19 5.8(4) . . . . ? C13 C14 C15 C16 0.5(4) . . . . ? C19 C14 C15 C16 -180.0(3) . . . . ? C14 C15 C16 C17 -0.7(5) . . . . ? C15 C16 C17 C18 1.0(5) . . . . ? C16 C17 C18 C13 -1.0(5) . . . . ? C14 C13 C18 C17 0.7(4) . . . . ? N1 C13 C18 C17 175.0(3) . . . . ? C13 C14 C19 F3 56.6(3) . . . . ? C15 C14 C19 F3 -122.9(3) . . . . ? C13 C14 C19 F2 177.5(2) . . . . ? C15 C14 C19 F2 -2.0(4) . . . . ? C13 C14 C19 F1 -62.7(3) . . . . ? C15 C14 C19 F1 117.8(3) . . . . ? C25 C20 C21 C22 1.7(4) . . . . ? N2 C20 C21 C22 175.1(2) . . . . ? C25 C20 C21 C26 -179.7(3) . . . . ? N2 C20 C21 C26 -6.4(4) . . . . ? C20 C21 C22 C23 -1.1(4) . . . . ? C26 C21 C22 C23 -179.7(3) . . . . ? C21 C22 C23 C24 0.0(4) . . . . ? C22 C23 C24 C25 0.6(4) . . . . ? C23 C24 C25 C20 0.0(4) . . . . ? C21 C20 C25 C24 -1.2(4) . . . . ? N2 C20 C25 C24 -174.6(2) . . . . ? C22 C21 C26 F4 -6.4(4) . . . . ? C20 C21 C26 F4 175.0(3) . . . . ? C22 C21 C26 F6 114.6(3) . . . . ? C20 C21 C26 F6 -63.9(4) . . . . ? C22 C21 C26 F5 -126.4(3) . . . . ? C20 C21 C26 F5 55.1(4) . . . . ? N3 C27 C28 C29 -13.8(5) . . . . ? C38 C27 C28 C29 172.9(3) . . . . ? N3 C27 C28 C37 165.5(2) . . . . ? C38 C27 C28 C37 -7.8(2) . . . . ? C37 C28 C29 C30 -0.9(3) . . . . ? C27 C28 C29 C30 178.3(3) . . . . ? C28 C29 C30 C31 -0.3(4) . . . . ? C29 C30 C31 C32 0.4(4) . . . . ? C30 C31 C32 C37 0.8(4) . . . . ? C30 C31 C32 C33 -179.7(2) . . . . ? C37 C32 C33 C34 1.0(3) . . . . ? C31 C32 C33 C34 -178.4(2) . . . . ? C32 C33 C34 C35 0.3(4) . . . . ? C33 C34 C35 C36 -1.1(4) . . . . ? C34 C35 C36 C37 0.3(3) . . . . ? C34 C35 C36 C38 177.1(2) . . . . ? C31 C32 C37 C36 177.7(2) . . . . ? C33 C32 C37 C36 -1.8(3) . . . . ? C31 C32 C37 C28 -2.1(3) . . . . ? C33 C32 C37 C28 178.3(2) . . . . ? C35 C36 C37 C32 1.1(4) . . . . ? C38 C36 C37 C32 -176.5(2) . . . . ? C35 C36 C37 C28 -179.0(2) . . . . ? C38 C36 C37 C28 3.4(3) . . . . ? C29 C28 C37 C32 2.2(3) . . . . ? C27 C28 C37 C32 -177.2(2) . . . . ? C29 C28 C37 C36 -177.7(2) . . . . ? C27 C28 C37 C36 2.9(3) . . . . ? C35 C36 C38 N4 -9.4(5) . . . . ? C37 C36 C38 N4 167.6(3) . . . . ? C35 C36 C38 C27 174.9(3) . . . . ? C37 C36 C38 C27 -8.1(2) . . . . ? N3 C27 C38 N4 19.1(3) . . . . ? C28 C27 C38 N4 -166.6(2) . . . . ? N3 C27 C38 C36 -164.5(2) . . . . ? C28 C27 C38 C36 9.9(2) . . . . ? C44 C39 C40 C41 -2.1(4) . . . . ? N3 C39 C40 C41 -177.0(2) . . . . ? C44 C39 C40 C45 177.9(2) . . . . ? N3 C39 C40 C45 2.9(4) . . . . ? C39 C40 C41 C42 0.7(4) . . . . ? C45 C40 C41 C42 -179.2(3) . . . . ? C40 C41 C42 C43 0.7(4) . . . . ? C41 C42 C43 C44 -0.8(4) . . . . ? C42 C43 C44 C39 -0.5(4) . . . . ? C40 C39 C44 C43 2.0(4) . . . . ? N3 C39 C44 C43 177.0(2) . . . . ? C41 C40 C45 F7 -1.6(4) . . . . ? C39 C40 C45 F7 178.4(2) . . . . ? C41 C40 C45 F9 -122.2(3) . . . . ? C39 C40 C45 F9 57.9(3) . . . . ? C41 C40 C45 F8 117.9(3) . . . . ? C39 C40 C45 F8 -62.1(4) . . . . ? C51 C46 C47 C48 1.0(4) . . . . ? N4 C46 C47 C48 -172.3(2) . . . . ? C51 C46 C47 C52 -179.2(3) . . . . ? N4 C46 C47 C52 7.4(4) . . . . ? C46 C47 C48 C49 -0.2(4) . . . . ? C52 C47 C48 C49 -179.9(3) . . . . ? C47 C48 C49 C50 -0.6(4) . . . . ? C48 C49 C50 C51 0.5(5) . . . . ? C49 C50 C51 C46 0.4(5) . . . . ? C47 C46 C51 C50 -1.2(4) . . . . ? N4 C46 C51 C50 172.4(3) . . . . ? C48 C47 C52 F12 -2.7(4) . . . . ? C46 C47 C52 F12 177.5(2) . . . . ? C48 C47 C52 F11 117.3(3) . . . . ? C46 C47 C52 F11 -62.5(3) . . . . ? C48 C47 C52 F10 -122.7(3) . . . . ? C46 C47 C52 F10 57.5(3) . . . . ? C2 C1 N1 C13 0.1(4) . . . . ? C12 C1 N1 C13 -179.4(2) . . . . ? C14 C13 N1 C1 -95.3(3) . . . . ? C18 C13 N1 C1 90.7(3) . . . . ? C10 C12 N2 C20 176.0(2) . . . . ? C1 C12 N2 C20 -1.7(4) . . . . ? C25 C20 N2 C12 -82.7(3) . . . . ? C21 C20 N2 C12 104.0(3) . . . . ? C28 C27 N3 C39 5.1(4) . . . . ? C38 C27 N3 C39 177.7(2) . . . . ? C44 C39 N3 C27 85.3(3) . . . . ? C40 C39 N3 C27 -99.8(3) . . . . ? C36 C38 N4 C46 7.4(4) . . . . ? C27 C38 N4 C46 -177.4(2) . . . . ? C51 C46 N4 C38 80.9(3) . . . . ? C47 C46 N4 C38 -105.8(3) . . . . ? _diffrn_measured_fraction_theta_max 0.936 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.959 _refine_diff_density_max 0.274 _refine_diff_density_min -0.325 _refine_diff_density_rms 0.058