# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2003 data_global _journal_coden_Cambridge 182 loop_ _publ_author_name 'Jeffrey Zaleski' 'Sibaprasad Bhattacharyya' 'Aurora E. Clark' 'Maren Pink' _publ_contact_author_name 'Prof Jeffrey Zaleski' _publ_contact_author_address ; Department of Chemistry Indiana University 800 East Kirkwood Ave. Bloomington IN 47405 UNITED STATES OF AMERICA ; _publ_contact_author_email ZALESKI@INDIANA.EDU _publ_requested_journal 'Chemical Communications' _publ_section_title ; Isolation of Electronic From Geometric Contributions To Bergman Cyclization of Metalloenediynes ; data_03007 _database_code_CSD 204062 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C24 H26 N2' _chemical_formula_sum 'C24 H26 N2' _chemical_formula_weight 342.47 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 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 5.6575(2) _cell_length_b 11.4775(4) _cell_length_c 14.8070(6) _cell_angle_alpha 82.9460(10) _cell_angle_beta 79.7450(10) _cell_angle_gamma 79.4360(10) _cell_volume 926.03(6) _cell_formula_units_Z 2 _cell_measurement_temperature 137(2) _cell_measurement_reflns_used 5484 _cell_measurement_theta_min 2.15 _cell_measurement_theta_max 27.44 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.228 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 368 _exptl_absorpt_coefficient_mu 0.072 _exptl_absorpt_correction_type multi-scans _exptl_absorpt_correction_T_min 0.9858 _exptl_absorpt_correction_T_max 0.9893 _exptl_absorpt_process_details 'SADABS, R. Blessing (1995)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 137(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_details '0.30 degree frames measured for 10 seconds each' _diffrn_measurement_method \w-scans _diffrn_measurement_device 'three-circle goniometer with fixed chi' _diffrn_measurement_device_type 'Bruker Platform goniometer' _diffrn_detector 'CCD area detector' _diffrn_detector_type 'Bruker SMART 6000' _diffrn_detector_area_resol_mean 44.52 _diffrn_standards_number 140 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 606 _diffrn_standards_decay_% 0.0 _diffrn_reflns_number 20665 _diffrn_reflns_av_R_equivalents 0.0288 _diffrn_reflns_av_sigmaI/netI 0.0228 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.19 _diffrn_reflns_theta_max 27.48 _reflns_number_total 4258 _reflns_number_gt 3564 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 1999)' _computing_cell_refinement 'SAINT (Bruker, 1999)' _computing_data_reduction 'SAINT (Bruker, 1999)' _computing_structure_solution 'SIR-92 (Alatomare et al., 1993)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'XTEL (local library)' _computing_publication_material 'XCIF (Bruker, 1999), XTEL (local library)' _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^)+(0.0532P)^2^+0.4285P] 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 4258 _refine_ls_number_parameters 261 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0536 _refine_ls_R_factor_gt 0.0445 _refine_ls_wR_factor_ref 0.1212 _refine_ls_wR_factor_gt 0.1137 _refine_ls_goodness_of_fit_ref 1.052 _refine_ls_restrained_S_all 1.052 _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 0.0683(2) -0.33063(10) 0.89664(8) 0.0251(2) Uani 1 1 d . . . N2 N 0.1579(2) -0.16661(9) 0.67893(8) 0.0228(2) Uani 1 1 d . . . C1 C 0.0747(3) -0.42853(12) 0.84042(10) 0.0271(3) Uani 1 1 d . . . H1A H -0.0744 -0.4120 0.8115 0.033(4) Uiso 1 1 calc R . . H1B H 0.0670 -0.5024 0.8823 0.033(4) Uiso 1 1 calc R . . C2 C 0.2934(2) -0.45242(11) 0.76453(9) 0.0226(3) Uani 1 1 d . . . C3 C 0.4886(3) -0.54107(12) 0.78215(9) 0.0258(3) Uani 1 1 d . . . H3A H 0.4797 -0.5865 0.8404 0.032(4) Uiso 1 1 calc R . . C4 C 0.6958(3) -0.56452(12) 0.71654(10) 0.0278(3) Uani 1 1 d . . . H4A H 0.8288 -0.6235 0.7306 0.032(4) Uiso 1 1 calc R . . C5 C 0.7065(3) -0.50123(12) 0.63057(10) 0.0300(3) Uani 1 1 d . . . H5A H 0.8463 -0.5173 0.5849 0.040(5) Uiso 1 1 calc R . . C6 C 0.5121(3) -0.41416(12) 0.61126(10) 0.0277(3) Uani 1 1 d . . . H6A H 0.5193 -0.3721 0.5517 0.037(5) Uiso 1 1 calc R . . C7 C 0.3065(2) -0.38705(11) 0.67743(9) 0.0228(3) Uani 1 1 d . . . C8 C 0.1119(2) -0.28207(12) 0.65720(10) 0.0258(3) Uani 1 1 d . . . H8A H 0.0979 -0.2762 0.5910 0.024(4) Uiso 1 1 calc R . . H8B H -0.0462 -0.2974 0.6931 0.027(4) Uiso 1 1 calc R . . C9 C 0.0189(2) -0.21096(12) 0.85019(9) 0.0248(3) Uani 1 1 d . . . H9A H -0.0152 -0.1537 0.8976 0.026(4) Uiso 1 1 calc R . . H9B H -0.1320 -0.2047 0.8235 0.030(4) Uiso 1 1 calc R . . C10 C 0.2163(2) -0.17075(12) 0.77336(9) 0.0236(3) Uani 1 1 d . . . H10A H 0.2412 -0.0906 0.7837 0.025(4) Uiso 1 1 calc R . . H10B H 0.3714 -0.2259 0.7775 0.019(3) Uiso 1 1 calc R . . C11 C 0.2726(2) -0.35171(12) 0.94811(9) 0.0254(3) Uani 1 1 d . . . H11A H 0.4257 -0.3475 0.9044 0.031(4) Uiso 1 1 calc R . . H11B H 0.2847 -0.4329 0.9805 0.035(4) Uiso 1 1 calc R . . C12 C 0.2447(2) -0.26227(12) 1.01780(9) 0.0230(3) Uani 1 1 d . . . C13 C 0.4283(3) -0.19700(14) 1.01866(10) 0.0321(3) Uani 1 1 d . . . H13A H 0.5725 -0.2080 0.9744 0.036(5) Uiso 1 1 calc R . . C14 C 0.4034(3) -0.11556(15) 1.08364(12) 0.0372(4) Uani 1 1 d . . . H14A H 0.5307 -0.0718 1.0835 0.051(6) Uiso 1 1 calc R . . C15 C 0.1950(3) -0.09824(13) 1.14807(10) 0.0322(3) Uani 1 1 d . . . H15A H 0.1783 -0.0428 1.1923 0.038(5) Uiso 1 1 calc R . . C16 C 0.0100(3) -0.16228(13) 1.14782(10) 0.0303(3) Uani 1 1 d . . . H16A H -0.1342 -0.1506 1.1920 0.043(5) Uiso 1 1 calc R . . C17 C 0.0351(2) -0.24354(12) 1.08310(9) 0.0260(3) Uani 1 1 d . . . H17A H -0.0928 -0.2870 1.0834 0.030(4) Uiso 1 1 calc R . . C18 C 0.3556(2) -0.12286(11) 0.61183(9) 0.0213(3) Uani 1 1 d . . . H18A H 0.3385 -0.1373 0.5489 0.024(4) Uiso 1 1 calc R . . H18B H 0.5146 -0.1675 0.6252 0.021(4) Uiso 1 1 calc R . . C19 C 0.3501(2) 0.00857(11) 0.61569(8) 0.0191(2) Uani 1 1 d . . . C20 C 0.1622(2) 0.09161(11) 0.58449(9) 0.0220(3) Uani 1 1 d . . . H20A H 0.0387 0.0650 0.5604 0.028(4) Uiso 1 1 calc R . . C21 C 0.1536(2) 0.21265(12) 0.58815(9) 0.0236(3) Uani 1 1 d . . . H21A H 0.0250 0.2681 0.5663 0.028(4) Uiso 1 1 calc R . . C22 C 0.3324(2) 0.25302(11) 0.62365(9) 0.0229(3) Uani 1 1 d . . . H22A H 0.3252 0.3357 0.6270 0.030(4) Uiso 1 1 calc R . . C23 C 0.5212(2) 0.17136(12) 0.65402(9) 0.0242(3) Uani 1 1 d . . . H23A H 0.6449 0.1983 0.6778 0.030(4) Uiso 1 1 calc R . . C24 C 0.5302(2) 0.04986(11) 0.64986(9) 0.0225(3) Uani 1 1 d . . . H24A H 0.6607 -0.0054 0.6706 0.025(4) Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.0286(6) 0.0210(5) 0.0249(6) -0.0020(4) -0.0044(4) -0.0017(4) N2 0.0234(5) 0.0177(5) 0.0262(6) 0.0005(4) -0.0022(4) -0.0042(4) C1 0.0310(7) 0.0217(6) 0.0290(7) -0.0030(5) -0.0018(5) -0.0075(5) C2 0.0283(6) 0.0169(6) 0.0244(6) -0.0030(5) -0.0049(5) -0.0069(5) C3 0.0360(7) 0.0183(6) 0.0239(6) -0.0017(5) -0.0075(5) -0.0043(5) C4 0.0311(7) 0.0184(6) 0.0344(7) -0.0069(5) -0.0068(6) -0.0007(5) C5 0.0352(7) 0.0217(7) 0.0316(7) -0.0080(5) 0.0039(6) -0.0063(5) C6 0.0415(8) 0.0186(6) 0.0231(6) -0.0012(5) -0.0026(6) -0.0084(5) C7 0.0301(7) 0.0168(6) 0.0241(6) -0.0022(5) -0.0074(5) -0.0077(5) C8 0.0285(7) 0.0221(6) 0.0294(7) 0.0010(5) -0.0095(5) -0.0081(5) C9 0.0245(6) 0.0241(6) 0.0248(6) -0.0018(5) -0.0024(5) -0.0029(5) C10 0.0233(6) 0.0224(6) 0.0260(6) -0.0048(5) -0.0038(5) -0.0041(5) C11 0.0267(6) 0.0256(7) 0.0205(6) 0.0001(5) -0.0018(5) 0.0008(5) C12 0.0246(6) 0.0233(6) 0.0190(6) 0.0040(5) -0.0043(5) -0.0015(5) C13 0.0253(7) 0.0382(8) 0.0320(7) 0.0013(6) -0.0026(6) -0.0078(6) C14 0.0365(8) 0.0369(8) 0.0434(9) 0.0005(7) -0.0171(7) -0.0125(6) C15 0.0424(8) 0.0257(7) 0.0302(7) -0.0030(6) -0.0168(6) 0.0013(6) C16 0.0344(7) 0.0289(7) 0.0239(7) -0.0015(5) -0.0022(6) 0.0013(6) C17 0.0266(7) 0.0245(6) 0.0251(6) 0.0015(5) -0.0017(5) -0.0048(5) C18 0.0251(6) 0.0188(6) 0.0188(6) -0.0014(5) -0.0014(5) -0.0030(5) C19 0.0215(6) 0.0192(6) 0.0151(5) -0.0019(4) 0.0014(4) -0.0037(5) C20 0.0216(6) 0.0232(6) 0.0216(6) -0.0029(5) -0.0036(5) -0.0038(5) C21 0.0246(6) 0.0216(6) 0.0226(6) -0.0010(5) -0.0035(5) 0.0006(5) C22 0.0285(6) 0.0191(6) 0.0200(6) -0.0026(5) 0.0015(5) -0.0052(5) C23 0.0257(6) 0.0258(7) 0.0227(6) -0.0028(5) -0.0040(5) -0.0083(5) C24 0.0221(6) 0.0227(6) 0.0213(6) 0.0001(5) -0.0034(5) -0.0020(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C9 1.4606(17) . ? N1 C11 1.4629(18) . ? N1 C1 1.4701(17) . ? N2 C18 1.4760(16) . ? N2 C8 1.4792(17) . ? N2 C10 1.4864(17) . ? C1 C2 1.5248(18) . ? C1 H1A 0.9900 . ? C1 H1B 0.9900 . ? C2 C3 1.3960(18) . ? C2 C7 1.4073(18) . ? C3 C4 1.390(2) . ? C3 H3A 0.9500 . ? C4 C5 1.383(2) . ? C4 H4A 0.9500 . ? C5 C6 1.389(2) . ? C5 H5A 0.9500 . ? C6 C7 1.3950(19) . ? C6 H6A 0.9500 . ? C7 C8 1.5152(18) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 C10 1.5371(18) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 C12 1.5121(19) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 C13 1.390(2) . ? C12 C17 1.3918(18) . ? C13 C14 1.394(2) . ? C13 H13A 0.9500 . ? C14 C15 1.379(2) . ? C14 H14A 0.9500 . ? C15 C16 1.386(2) . ? C15 H15A 0.9500 . ? C16 C17 1.390(2) . ? C16 H16A 0.9500 . ? C17 H17A 0.9500 . ? C18 C19 1.5110(17) . ? C18 H18A 0.9900 . ? C18 H18B 0.9900 . ? C19 C24 1.3921(18) . ? C19 C20 1.3953(17) . ? C20 C21 1.3885(18) . ? C20 H20A 0.9500 . ? C21 C22 1.3913(19) . ? C21 H21A 0.9500 . ? C22 C23 1.3861(19) . ? C22 H22A 0.9500 . ? C23 C24 1.3946(18) . ? C23 H23A 0.9500 . ? C24 H24A 0.9500 . ? 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 C9 N1 C11 115.12(11) . . ? C9 N1 C1 115.44(11) . . ? C11 N1 C1 112.05(11) . . ? C18 N2 C8 111.73(10) . . ? C18 N2 C10 108.89(10) . . ? C8 N2 C10 113.03(10) . . ? N1 C1 C2 117.18(11) . . ? N1 C1 H1A 108.0 . . ? C2 C1 H1A 108.0 . . ? N1 C1 H1B 108.0 . . ? C2 C1 H1B 108.0 . . ? H1A C1 H1B 107.2 . . ? C3 C2 C7 118.74(12) . . ? C3 C2 C1 119.07(12) . . ? C7 C2 C1 122.19(12) . . ? C4 C3 C2 121.64(12) . . ? C4 C3 H3A 119.2 . . ? C2 C3 H3A 119.2 . . ? C5 C4 C3 119.41(13) . . ? C5 C4 H4A 120.3 . . ? C3 C4 H4A 120.3 . . ? C4 C5 C6 119.72(13) . . ? C4 C5 H5A 120.1 . . ? C6 C5 H5A 120.1 . . ? C5 C6 C7 121.45(13) . . ? C5 C6 H6A 119.3 . . ? C7 C6 H6A 119.3 . . ? C6 C7 C2 118.99(12) . . ? C6 C7 C8 119.65(12) . . ? C2 C7 C8 121.17(12) . . ? N2 C8 C7 114.41(11) . . ? N2 C8 H8A 108.7 . . ? C7 C8 H8A 108.7 . . ? N2 C8 H8B 108.7 . . ? C7 C8 H8B 108.7 . . ? H8A C8 H8B 107.6 . . ? N1 C9 C10 117.89(11) . . ? N1 C9 H9A 107.8 . . ? C10 C9 H9A 107.8 . . ? N1 C9 H9B 107.8 . . ? C10 C9 H9B 107.8 . . ? H9A C9 H9B 107.2 . . ? N2 C10 C9 113.96(11) . . ? N2 C10 H10A 108.8 . . ? C9 C10 H10A 108.8 . . ? N2 C10 H10B 108.8 . . ? C9 C10 H10B 108.8 . . ? H10A C10 H10B 107.7 . . ? N1 C11 C12 112.22(11) . . ? N1 C11 H11A 109.2 . . ? C12 C11 H11A 109.2 . . ? N1 C11 H11B 109.2 . . ? C12 C11 H11B 109.2 . . ? H11A C11 H11B 107.9 . . ? C13 C12 C17 118.23(13) . . ? C13 C12 C11 120.89(12) . . ? C17 C12 C11 120.88(12) . . ? C12 C13 C14 120.80(14) . . ? C12 C13 H13A 119.6 . . ? C14 C13 H13A 119.6 . . ? C15 C14 C13 120.31(14) . . ? C15 C14 H14A 119.8 . . ? C13 C14 H14A 119.8 . . ? C14 C15 C16 119.55(14) . . ? C14 C15 H15A 120.2 . . ? C16 C15 H15A 120.2 . . ? C15 C16 C17 120.11(14) . . ? C15 C16 H16A 119.9 . . ? C17 C16 H16A 119.9 . . ? C16 C17 C12 121.00(13) . . ? C16 C17 H17A 119.5 . . ? C12 C17 H17A 119.5 . . ? N2 C18 C19 111.26(10) . . ? N2 C18 H18A 109.4 . . ? C19 C18 H18A 109.4 . . ? N2 C18 H18B 109.4 . . ? C19 C18 H18B 109.4 . . ? H18A C18 H18B 108.0 . . ? C24 C19 C20 118.49(12) . . ? C24 C19 C18 121.39(11) . . ? C20 C19 C18 120.12(11) . . ? C21 C20 C19 120.84(12) . . ? C21 C20 H20A 119.6 . . ? C19 C20 H20A 119.6 . . ? C20 C21 C22 120.28(12) . . ? C20 C21 H21A 119.9 . . ? C22 C21 H21A 119.9 . . ? C23 C22 C21 119.35(12) . . ? C23 C22 H22A 120.3 . . ? C21 C22 H22A 120.3 . . ? C22 C23 C24 120.28(12) . . ? C22 C23 H23A 119.9 . . ? C24 C23 H23A 119.9 . . ? C19 C24 C23 120.75(12) . . ? C19 C24 H24A 119.6 . . ? C23 C24 H24A 119.6 . . ? 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 C9 N1 C1 C2 72.07(15) . . . . ? C11 N1 C1 C2 -62.35(15) . . . . ? N1 C1 C2 C3 96.55(15) . . . . ? N1 C1 C2 C7 -82.68(16) . . . . ? C7 C2 C3 C4 1.12(19) . . . . ? C1 C2 C3 C4 -178.13(12) . . . . ? C2 C3 C4 C5 -2.1(2) . . . . ? C3 C4 C5 C6 0.9(2) . . . . ? C4 C5 C6 C7 1.3(2) . . . . ? C5 C6 C7 C2 -2.2(2) . . . . ? C5 C6 C7 C8 172.94(12) . . . . ? C3 C2 C7 C6 0.97(18) . . . . ? C1 C2 C7 C6 -179.80(12) . . . . ? C3 C2 C7 C8 -174.06(12) . . . . ? C1 C2 C7 C8 5.17(19) . . . . ? C18 N2 C8 C7 72.91(14) . . . . ? C10 N2 C8 C7 -50.34(15) . . . . ? C6 C7 C8 N2 -86.00(15) . . . . ? C2 C7 C8 N2 89.00(15) . . . . ? C11 N1 C9 C10 63.55(15) . . . . ? C1 N1 C9 C10 -69.47(15) . . . . ? C18 N2 C10 C9 177.97(10) . . . . ? C8 N2 C10 C9 -57.23(14) . . . . ? N1 C9 C10 N2 106.29(13) . . . . ? C9 N1 C11 C12 55.00(15) . . . . ? C1 N1 C11 C12 -170.42(11) . . . . ? N1 C11 C12 C13 -126.43(13) . . . . ? N1 C11 C12 C17 53.89(16) . . . . ? C17 C12 C13 C14 0.4(2) . . . . ? C11 C12 C13 C14 -179.27(13) . . . . ? C12 C13 C14 C15 -0.2(2) . . . . ? C13 C14 C15 C16 0.0(2) . . . . ? C14 C15 C16 C17 0.1(2) . . . . ? C15 C16 C17 C12 0.1(2) . . . . ? C13 C12 C17 C16 -0.3(2) . . . . ? C11 C12 C17 C16 179.34(12) . . . . ? C8 N2 C18 C19 162.31(10) . . . . ? C10 N2 C18 C19 -72.13(13) . . . . ? N2 C18 C19 C24 110.48(13) . . . . ? N2 C18 C19 C20 -69.65(15) . . . . ? C24 C19 C20 C21 -0.57(18) . . . . ? C18 C19 C20 C21 179.56(11) . . . . ? C19 C20 C21 C22 -0.36(19) . . . . ? C20 C21 C22 C23 0.97(19) . . . . ? C21 C22 C23 C24 -0.65(19) . . . . ? C20 C19 C24 C23 0.89(18) . . . . ? C18 C19 C24 C23 -179.24(11) . . . . ? C22 C23 C24 C19 -0.29(19) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.615 _refine_diff_density_min -0.291 _refine_diff_density_rms 0.042 data_02027 _database_code_CSD 204063 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C24 H24 N2' _chemical_formula_sum 'C24 H24 N2' _chemical_formula_weight 340.45 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 orthorhombic _symmetry_space_group_name_H-M Pccn loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y+1/2, z' 'x+1/2, -y, -z+1/2' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y-1/2, -z' '-x-1/2, y, z-1/2' 'x, -y-1/2, z-1/2' _cell_length_a 15.2536(4) _cell_length_b 34.7020(10) _cell_length_c 7.1210(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3769.36(18) _cell_formula_units_Z 8 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 8405 _cell_measurement_theta_min 2.22 _cell_measurement_theta_max 39.60 _exptl_crystal_description block _exptl_crystal_colour brownish _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.200 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1456 _exptl_absorpt_coefficient_mu 0.070 _exptl_absorpt_correction_type multi-scans _exptl_absorpt_correction_T_min 0.9793 _exptl_absorpt_correction_T_max 0.9930 _exptl_absorpt_process_details 'SADABS, R. Blessing (1995)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_details '0.30 degree frames measured for 5 seconds each' _diffrn_measurement_method \w-scans _diffrn_measurement_device 'three-circle goniometer with fixed chi' _diffrn_measurement_device_type 'Bruker Platform goniometer' _diffrn_detector 'CCD area detector' _diffrn_detector_type 'Bruker SMART 6000' _diffrn_detector_area_resol_mean 44.52 _diffrn_standards_number 614 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 151 _diffrn_standards_decay_% 0.0 _diffrn_reflns_number 68430 _diffrn_reflns_av_R_equivalents 0.0459 _diffrn_reflns_av_sigmaI/netI 0.0268 _diffrn_reflns_limit_h_min -24 _diffrn_reflns_limit_h_max 24 _diffrn_reflns_limit_k_min -54 _diffrn_reflns_limit_k_max 55 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.21 _diffrn_reflns_theta_max 35.00 _reflns_number_total 8308 _reflns_number_gt 6378 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 1999)' _computing_cell_refinement 'SAINT (Bruker, 1999)' _computing_data_reduction 'SAINT (Bruker, 1999)' _computing_structure_solution 'SIR-92 (Alatomare et al., 1993)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'XTEL (local library)' _computing_publication_material 'XCIF (Bruker, 1999), XTEL (local library)' _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^)+(0.0846P)^2^+0.3427P] 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 riding _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 8308 _refine_ls_number_parameters 259 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0653 _refine_ls_R_factor_gt 0.0480 _refine_ls_wR_factor_ref 0.1462 _refine_ls_wR_factor_gt 0.1315 _refine_ls_goodness_of_fit_ref 1.100 _refine_ls_restrained_S_all 1.100 _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 N1 N 0.47891(5) 0.14266(2) -0.25846(9) 0.01739(12) Uani 1 1 d . . . N2 N 0.56990(4) 0.066951(19) -0.58560(10) 0.01799(13) Uani 1 1 d . . . C1 C 0.45388(5) 0.17356(2) -0.38909(12) 0.01967(14) Uani 1 1 d . . . H1A H 0.4201 0.1932 -0.3189 0.029(3) Uiso 1 1 calc R . . H1B H 0.4146 0.1626 -0.4860 0.018(3) Uiso 1 1 calc R . . C2 C 0.52787(6) 0.19288(2) -0.48424(12) 0.02107(15) Uani 1 1 d . . . C3 C 0.58693(6) 0.20410(2) -0.58216(13) 0.02305(16) Uani 1 1 d . . . C4 C 0.65501(7) 0.21344(3) -0.71159(14) 0.02725(18) Uani 1 1 d . . . H4 H 0.6642 0.2396 -0.7455 0.042(4) Uiso 1 1 calc R . . C5 C 0.70652(6) 0.18594(3) -0.78687(14) 0.02834(19) Uani 1 1 d . . . H5 H 0.7503 0.1931 -0.8750 0.037(4) Uiso 1 1 calc R . . C6 C 0.69695(6) 0.14636(3) -0.73753(13) 0.02505(17) Uani 1 1 d . . . C7 C 0.68475(5) 0.11396(3) -0.68238(13) 0.02323(16) Uani 1 1 d . . . C8 C 0.66372(5) 0.07693(2) -0.59097(13) 0.02146(15) Uani 1 1 d . . . H8A H 0.6955 0.0561 -0.6576 0.027(3) Uiso 1 1 calc R . . H8B H 0.6861 0.0777 -0.4605 0.024(3) Uiso 1 1 calc R . . C9 C 0.54435(5) 0.11592(2) -0.33554(11) 0.01841(14) Uani 1 1 d . . . H9A H 0.5541 0.0946 -0.2454 0.028(3) Uiso 1 1 calc R . . H9B H 0.6007 0.1297 -0.3525 0.020(3) Uiso 1 1 calc R . . C10 C 0.51492(5) 0.09931(2) -0.52318(11) 0.01777(14) Uani 1 1 d . . . H10A H 0.4535 0.0904 -0.5120 0.024(3) Uiso 1 1 calc R . . H10B H 0.5167 0.1199 -0.6194 0.017(3) Uiso 1 1 calc R . . C11 C 0.50884(5) 0.15913(2) -0.07899(11) 0.01910(14) Uani 1 1 d . . . H11A H 0.5467 0.1817 -0.1038 0.021(3) Uiso 1 1 calc R . . H11B H 0.5440 0.1398 -0.0103 0.027(3) Uiso 1 1 calc R . . C12 C 0.43189(5) 0.17126(2) 0.04020(11) 0.01678(13) Uani 1 1 d . . . C13 C 0.41841(5) 0.20929(2) 0.09512(12) 0.02032(15) Uani 1 1 d . . . H13 H 0.4583 0.2287 0.0560 0.026(3) Uiso 1 1 calc R . . C14 C 0.34679(6) 0.21902(2) 0.20720(13) 0.02302(16) Uani 1 1 d . . . H14 H 0.3384 0.2450 0.2446 0.038(4) Uiso 1 1 calc R . . C15 C 0.28782(6) 0.19104(3) 0.26436(12) 0.02188(15) Uani 1 1 d . . . H15 H 0.2392 0.1978 0.3409 0.032(3) Uiso 1 1 calc R . . C16 C 0.30026(6) 0.15295(3) 0.20889(12) 0.02217(15) Uani 1 1 d . . . H16 H 0.2598 0.1336 0.2468 0.037(4) Uiso 1 1 calc R . . C17 C 0.37178(6) 0.14325(2) 0.09820(12) 0.02025(15) Uani 1 1 d . . . H17 H 0.3801 0.1172 0.0613 0.025(3) Uiso 1 1 calc R . . C18 C 0.53759(5) 0.05383(2) -0.76993(12) 0.02033(15) Uani 1 1 d . . . H18A H 0.5422 0.0754 -0.8606 0.022(3) Uiso 1 1 calc R . . H18B H 0.4748 0.0470 -0.7584 0.029(3) Uiso 1 1 calc R . . C19 C 0.58702(5) 0.01962(2) -0.84611(12) 0.01838(14) Uani 1 1 d . . . C20 C 0.58031(6) -0.01662(2) -0.76179(13) 0.02162(15) Uani 1 1 d . . . H20 H 0.5434 -0.0200 -0.6556 0.030(3) Uiso 1 1 calc R . . C21 C 0.62750(6) -0.04777(2) -0.83286(13) 0.02378(16) Uani 1 1 d . . . H21 H 0.6227 -0.0723 -0.7751 0.033(4) Uiso 1 1 calc R . . C22 C 0.68175(6) -0.04291(2) -0.98864(13) 0.02397(17) Uani 1 1 d . . . H22 H 0.7149 -0.0640 -1.0352 0.034(3) Uiso 1 1 calc R . . C23 C 0.68733(6) -0.00726(3) -1.07543(13) 0.02454(17) Uani 1 1 d . . . H23 H 0.7233 -0.0040 -1.1832 0.032(3) Uiso 1 1 calc R . . C24 C 0.64005(6) 0.02378(2) -1.00405(13) 0.02197(15) Uani 1 1 d . . . H24 H 0.6440 0.0482 -1.0640 0.026(3) Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.0183(3) 0.0178(3) 0.0161(3) -0.0003(2) -0.0002(2) 0.0039(2) N2 0.0170(3) 0.0162(3) 0.0208(3) -0.0026(2) -0.0004(2) 0.0022(2) C1 0.0193(3) 0.0199(3) 0.0198(3) 0.0011(3) -0.0009(3) 0.0049(2) C2 0.0251(4) 0.0173(3) 0.0208(3) 0.0007(3) -0.0031(3) 0.0032(3) C3 0.0273(4) 0.0192(3) 0.0226(4) 0.0022(3) -0.0044(3) -0.0002(3) C4 0.0308(4) 0.0256(4) 0.0254(4) 0.0056(3) -0.0014(3) -0.0072(3) C5 0.0291(4) 0.0315(4) 0.0243(4) 0.0024(3) 0.0036(3) -0.0095(3) C6 0.0209(4) 0.0305(4) 0.0237(4) -0.0045(3) 0.0033(3) -0.0044(3) C7 0.0171(3) 0.0276(4) 0.0250(4) -0.0064(3) 0.0024(3) -0.0013(3) C8 0.0173(3) 0.0211(3) 0.0260(4) -0.0050(3) -0.0023(3) 0.0037(3) C9 0.0188(3) 0.0178(3) 0.0186(3) 0.0001(3) -0.0003(2) 0.0045(2) C10 0.0166(3) 0.0167(3) 0.0199(3) -0.0009(2) 0.0009(2) 0.0024(2) C11 0.0180(3) 0.0211(3) 0.0181(3) -0.0013(3) -0.0015(2) 0.0010(2) C12 0.0188(3) 0.0157(3) 0.0157(3) -0.0009(2) -0.0017(2) 0.0007(2) C13 0.0217(3) 0.0155(3) 0.0237(4) -0.0015(3) -0.0025(3) -0.0003(2) C14 0.0259(4) 0.0183(3) 0.0249(4) -0.0048(3) -0.0024(3) 0.0050(3) C15 0.0225(3) 0.0254(4) 0.0177(3) -0.0013(3) -0.0003(3) 0.0055(3) C16 0.0238(4) 0.0225(4) 0.0202(3) 0.0010(3) 0.0019(3) -0.0015(3) C17 0.0246(4) 0.0158(3) 0.0204(3) -0.0018(3) 0.0013(3) -0.0009(3) C18 0.0197(3) 0.0185(3) 0.0228(4) -0.0023(3) -0.0020(3) 0.0019(3) C19 0.0179(3) 0.0164(3) 0.0208(3) -0.0028(3) -0.0007(3) -0.0012(2) C20 0.0239(3) 0.0179(3) 0.0230(4) -0.0021(3) 0.0032(3) -0.0019(3) C21 0.0268(4) 0.0164(3) 0.0282(4) -0.0032(3) 0.0038(3) -0.0022(3) C22 0.0239(4) 0.0179(3) 0.0301(4) -0.0076(3) 0.0046(3) -0.0028(3) C23 0.0241(4) 0.0221(4) 0.0274(4) -0.0045(3) 0.0069(3) -0.0040(3) C24 0.0226(3) 0.0193(3) 0.0240(4) -0.0010(3) 0.0030(3) -0.0024(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C9 1.4692(10) . ? N1 C1 1.4700(10) . ? N1 C11 1.4726(10) . ? N2 C10 1.4704(10) . ? N2 C8 1.4728(11) . ? N2 C18 1.4742(11) . ? C1 C2 1.4772(12) . ? C1 H1A 0.9900 . ? C1 H1B 0.9900 . ? C2 C3 1.2039(13) . ? C3 C4 1.4258(13) . ? C4 C5 1.3475(15) . ? C4 H4 0.9500 . ? C5 C6 1.4252(14) . ? C5 H5 0.9500 . ? C6 C7 1.2054(13) . ? C7 C8 1.4758(13) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 C10 1.5229(11) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 C12 1.5084(11) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 C13 1.3916(11) . ? C12 C17 1.3987(11) . ? C13 C14 1.3945(12) . ? C13 H13 0.9500 . ? C14 C15 1.3846(13) . ? C14 H14 0.9500 . ? C15 C16 1.3924(12) . ? C15 H15 0.9500 . ? C16 C17 1.3875(12) . ? C16 H16 0.9500 . ? C17 H17 0.9500 . ? C18 C19 1.5073(11) . ? C18 H18A 0.9900 . ? C18 H18B 0.9900 . ? C19 C24 1.3928(12) . ? C19 C20 1.3975(11) . ? C20 C21 1.3937(12) . ? C20 H20 0.9500 . ? C21 C22 1.3942(13) . ? C21 H21 0.9500 . ? C22 C23 1.3857(13) . ? C22 H22 0.9500 . ? C23 C24 1.3923(12) . ? C23 H23 0.9500 . ? C24 H24 0.9500 . ? 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 C9 N1 C1 113.63(6) . . ? C9 N1 C11 111.03(6) . . ? C1 N1 C11 110.28(6) . . ? C10 N2 C8 112.49(6) . . ? C10 N2 C18 108.32(6) . . ? C8 N2 C18 111.98(7) . . ? N1 C1 C2 115.02(7) . . ? N1 C1 H1A 108.5 . . ? C2 C1 H1A 108.5 . . ? N1 C1 H1B 108.5 . . ? C2 C1 H1B 108.5 . . ? H1A C1 H1B 107.5 . . ? C3 C2 C1 169.78(9) . . ? C2 C3 C4 173.17(10) . . ? C5 C4 C3 121.39(9) . . ? C5 C4 H4 119.3 . . ? C3 C4 H4 119.3 . . ? C4 C5 C6 121.65(9) . . ? C4 C5 H5 119.2 . . ? C6 C5 H5 119.2 . . ? C7 C6 C5 174.29(10) . . ? C6 C7 C8 171.67(9) . . ? N2 C8 C7 115.30(7) . . ? N2 C8 H8A 108.4 . . ? C7 C8 H8A 108.4 . . ? N2 C8 H8B 108.4 . . ? C7 C8 H8B 108.4 . . ? H8A C8 H8B 107.5 . . ? N1 C9 C10 111.51(6) . . ? N1 C9 H9A 109.3 . . ? C10 C9 H9A 109.3 . . ? N1 C9 H9B 109.3 . . ? C10 C9 H9B 109.3 . . ? H9A C9 H9B 108.0 . . ? N2 C10 C9 112.72(6) . . ? N2 C10 H10A 109.0 . . ? C9 C10 H10A 109.0 . . ? N2 C10 H10B 109.0 . . ? C9 C10 H10B 109.0 . . ? H10A C10 H10B 107.8 . . ? N1 C11 C12 110.82(6) . . ? N1 C11 H11A 109.5 . . ? C12 C11 H11A 109.5 . . ? N1 C11 H11B 109.5 . . ? C12 C11 H11B 109.5 . . ? H11A C11 H11B 108.1 . . ? C13 C12 C17 118.64(7) . . ? C13 C12 C11 122.53(7) . . ? C17 C12 C11 118.83(7) . . ? C12 C13 C14 120.41(8) . . ? C12 C13 H13 119.8 . . ? C14 C13 H13 119.8 . . ? C15 C14 C13 120.50(8) . . ? C15 C14 H14 119.8 . . ? C13 C14 H14 119.8 . . ? C14 C15 C16 119.58(8) . . ? C14 C15 H15 120.2 . . ? C16 C15 H15 120.2 . . ? C17 C16 C15 119.92(8) . . ? C17 C16 H16 120.0 . . ? C15 C16 H16 120.0 . . ? C16 C17 C12 120.96(7) . . ? C16 C17 H17 119.5 . . ? C12 C17 H17 119.5 . . ? N2 C18 C19 113.35(7) . . ? N2 C18 H18A 108.9 . . ? C19 C18 H18A 108.9 . . ? N2 C18 H18B 108.9 . . ? C19 C18 H18B 108.9 . . ? H18A C18 H18B 107.7 . . ? C24 C19 C20 118.86(7) . . ? C24 C19 C18 119.97(7) . . ? C20 C19 C18 121.17(8) . . ? C21 C20 C19 120.27(8) . . ? C21 C20 H20 119.9 . . ? C19 C20 H20 119.9 . . ? C20 C21 C22 120.12(8) . . ? C20 C21 H21 119.9 . . ? C22 C21 H21 119.9 . . ? C23 C22 C21 119.95(8) . . ? C23 C22 H22 120.0 . . ? C21 C22 H22 120.0 . . ? C22 C23 C24 119.74(8) . . ? C22 C23 H23 120.1 . . ? C24 C23 H23 120.1 . . ? C23 C24 C19 121.04(8) . . ? C23 C24 H24 119.5 . . ? C19 C24 H24 119.5 . . ? 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 _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C9 N1 C1 C2 -46.33(9) . . . . ? C11 N1 C1 C2 79.05(8) . . . . ? N1 C1 C2 C3 87.1(5) . . . . ? C1 C2 C3 C4 -2.8(12) . . . . ? C2 C3 C4 C5 -38.3(8) . . . . ? C3 C4 C5 C6 -1.55(15) . . . . ? C4 C5 C6 C7 -16.8(11) . . . . ? C5 C6 C7 C8 -4.5(15) . . . . ? C10 N2 C8 C7 -46.86(10) . . . . ? C18 N2 C8 C7 75.41(9) . . . . ? C6 C7 C8 N2 69.8(7) . . . . ? C1 N1 C9 C10 -53.87(9) . . . . ? C11 N1 C9 C10 -178.86(6) . . . . ? C8 N2 C10 C9 -54.05(9) . . . . ? C18 N2 C10 C9 -178.37(6) . . . . ? N1 C9 C10 N2 -168.59(6) . . . . ? C9 N1 C11 C12 -154.52(7) . . . . ? C1 N1 C11 C12 78.64(8) . . . . ? N1 C11 C12 C13 -118.42(8) . . . . ? N1 C11 C12 C17 61.70(9) . . . . ? C17 C12 C13 C14 0.61(12) . . . . ? C11 C12 C13 C14 -179.27(8) . . . . ? C12 C13 C14 C15 -0.42(13) . . . . ? C13 C14 C15 C16 -0.14(13) . . . . ? C14 C15 C16 C17 0.48(13) . . . . ? C15 C16 C17 C12 -0.27(13) . . . . ? C13 C12 C17 C16 -0.27(12) . . . . ? C11 C12 C17 C16 179.61(8) . . . . ? C10 N2 C18 C19 -177.97(7) . . . . ? C8 N2 C18 C19 57.41(9) . . . . ? N2 C18 C19 C24 -111.76(9) . . . . ? N2 C18 C19 C20 68.70(10) . . . . ? C24 C19 C20 C21 1.34(13) . . . . ? C18 C19 C20 C21 -179.11(8) . . . . ? C19 C20 C21 C22 0.02(14) . . . . ? C20 C21 C22 C23 -1.38(14) . . . . ? C21 C22 C23 C24 1.34(14) . . . . ? C22 C23 C24 C19 0.05(14) . . . . ? C20 C19 C24 C23 -1.39(13) . . . . ? C18 C19 C24 C23 179.06(8) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 35.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.564 _refine_diff_density_min -0.166 _refine_diff_density_rms 0.060 data_02050 _database_code_CSD 204064 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C24 H24 Cl2 N2 Zn' _chemical_formula_sum 'C24 H24 Cl2 N2 Zn' _chemical_formula_weight 476.72 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 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 19.6558(19) _cell_length_b 15.9396(15) _cell_length_c 7.0274(7) _cell_angle_alpha 90.00 _cell_angle_beta 99.317(2) _cell_angle_gamma 90.00 _cell_volume 2172.7(4) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 5663 _cell_measurement_theta_min 2.5 _cell_measurement_theta_max 27.5 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_min 0.09 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.457 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 984 _exptl_absorpt_coefficient_mu 1.389 _exptl_absorpt_correction_type multi-scans _exptl_absorpt_correction_T_min 0.7227 _exptl_absorpt_correction_T_max 0.8852 _exptl_absorpt_process_details 'SADABS, R. Blessing (1995)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_details '0.30 degree frames measured for 30 seconds each' _diffrn_measurement_method \w-scans _diffrn_measurement_device 'three-circle goniometer with fixed chi' _diffrn_measurement_device_type 'Bruker Platform goniometer' _diffrn_detector 'CCD area detector' _diffrn_detector_type 'Bruker SMART 6000' _diffrn_detector_area_resol_mean 44.52 _diffrn_standards_number 268 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 909 _diffrn_standards_decay_% 0.0 _diffrn_reflns_number 12277 _diffrn_reflns_av_R_equivalents 0.0170 _diffrn_reflns_av_sigmaI/netI 0.0326 _diffrn_reflns_limit_h_min -25 _diffrn_reflns_limit_h_max 25 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 2.10 _diffrn_reflns_theta_max 27.51 _reflns_number_total 4949 _reflns_number_gt 4848 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 1999)' _computing_cell_refinement 'SAINT (Bruker, 1999)' _computing_data_reduction 'SAINT (Bruker, 1999)' _computing_structure_solution 'SIR-92 (Alatomare et al., 1993)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'XTEL (local library)' _computing_publication_material 'XCIF (Bruker, 1999), XTEL (local library)' _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. The sample is twinned, domain ratio see Flack parameter. ; _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^)+(0.0596P)^2^+1.7391P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.203(9) _refine_ls_number_reflns 4949 _refine_ls_number_parameters 283 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0334 _refine_ls_R_factor_gt 0.0329 _refine_ls_wR_factor_ref 0.0867 _refine_ls_wR_factor_gt 0.0864 _refine_ls_goodness_of_fit_ref 1.055 _refine_ls_restrained_S_all 1.055 _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 Zn1 Zn 0.776935(16) 0.193496(15) 1.21742(3) 0.01504(8) Uani 1 1 d . . . Cl1 Cl 0.75534(4) 0.29724(4) 1.40393(9) 0.02214(14) Uani 1 1 d . . . Cl2 Cl 0.79276(3) 0.07116(4) 1.37598(8) 0.01837(12) Uani 1 1 d . . . N1 N 0.70788(11) 0.17489(13) 0.9552(3) 0.0144(4) Uani 1 1 d . . . N2 N 0.85898(11) 0.20335(13) 1.0580(3) 0.0153(4) Uani 1 1 d . . . C1 C 0.65803(13) 0.24429(16) 0.8863(4) 0.0207(5) Uani 1 1 d . . . H1A H 0.6373 0.2327 0.7509 0.024(9) Uiso 1 1 calc R . . H1B H 0.6204 0.2433 0.9643 0.013(7) Uiso 1 1 calc R . . C2 C 0.68784(13) 0.32873(17) 0.8963(4) 0.0186(5) Uani 1 1 d . . . C3 C 0.70684(13) 0.39974(16) 0.9099(4) 0.0187(5) Uani 1 1 d . . . C4 C 0.73641(15) 0.48205(16) 0.9409(4) 0.0218(5) Uani 1 1 d . . . H4 H 0.7084 0.5299 0.9057 0.046(12) Uiso 1 1 calc R . . C5 C 0.80192(15) 0.49232(16) 1.0175(4) 0.0218(5) Uani 1 1 d . . . H5 H 0.8199 0.5474 1.0404 0.021(8) Uiso 1 1 calc R . . C6 C 0.84581(13) 0.42189(16) 1.0662(4) 0.0197(5) Uani 1 1 d . . . C7 C 0.87529(13) 0.35616(16) 1.0989(4) 0.0194(5) Uani 1 1 d . . . C8 C 0.90815(13) 0.27410(16) 1.1210(4) 0.0210(5) Uani 1 1 d . . . H8A H 0.9285 0.2658 1.2580 0.017(8) Uiso 1 1 calc R . . H8B H 0.9461 0.2725 1.0442 0.016(7) Uiso 1 1 calc R . . C9 C 0.75862(13) 0.16166(18) 0.8182(4) 0.0204(5) Uani 1 1 d . . . H9A H 0.7349 0.1719 0.6848 0.024 Uiso 1 1 calc R . . H9B H 0.7739 0.1024 0.8263 0.024 Uiso 1 1 calc R . . C10 C 0.82155(13) 0.21793(17) 0.8583(4) 0.0166(4) Uani 1 1 d . . . H10A H 0.8527 0.2060 0.7640 0.020 Uiso 1 1 calc R . . H10B H 0.8071 0.2774 0.8436 0.020 Uiso 1 1 calc R . . C11 C 0.66665(13) 0.09513(15) 0.9541(4) 0.0168(5) Uani 1 1 d . . . H11A H 0.6972 0.0504 1.0172 0.044(12) Uiso 1 1 calc R . . H11B H 0.6512 0.0780 0.8186 0.013(7) Uiso 1 1 calc R . . C12 C 0.60429(14) 0.10136(16) 1.0540(4) 0.0186(5) Uani 1 1 d . . . C13 C 0.53898(15) 0.0867(2) 0.9473(4) 0.0266(6) Uani 1 1 d . . . H13 H 0.5345 0.0733 0.8141 0.022(8) Uiso 1 1 calc R . . C14 C 0.48018(16) 0.0916(2) 1.0350(5) 0.0348(7) Uani 1 1 d . . . H14 H 0.4361 0.0805 0.9614 0.037(11) Uiso 1 1 calc R . . C15 C 0.48542(16) 0.1122(2) 1.2265(5) 0.0325(7) Uani 1 1 d . . . H15 H 0.4453 0.1163 1.2851 0.044(12) Uiso 1 1 calc R . . C16 C 0.55044(16) 0.1271(2) 1.3341(5) 0.0306(7) Uani 1 1 d . . . H16 H 0.5545 0.1415 1.4667 0.044(12) Uiso 1 1 calc R . . C17 C 0.60907(15) 0.1211(2) 1.2491(4) 0.0252(6) Uani 1 1 d . . . H17 H 0.6531 0.1305 1.3244 0.027(10) Uiso 1 1 calc R . . C18 C 0.89933(13) 0.12218(16) 1.0754(4) 0.0181(5) Uani 1 1 d . . . H18A H 0.8669 0.0755 1.0358 0.027(9) Uiso 1 1 calc R . . H18B H 0.9189 0.1135 1.2128 0.039(11) Uiso 1 1 calc R . . C19 C 0.95744(13) 0.11719(15) 0.9580(4) 0.0175(5) Uani 1 1 d . . . C20 C 1.02474(15) 0.13690(18) 1.0429(4) 0.0226(6) Uani 1 1 d . . . H20 H 1.0338 0.1537 1.1742 0.028(9) Uiso 1 1 calc R . . C21 C 1.07850(15) 0.1322(2) 0.9378(5) 0.0277(6) Uani 1 1 d . . . H21 H 1.1240 0.1458 0.9974 0.033(10) Uiso 1 1 calc R . . C22 C 1.06615(16) 0.1077(2) 0.7469(5) 0.0295(6) Uani 1 1 d . . . H22 H 1.1029 0.1062 0.6741 0.035(10) Uiso 1 1 calc R . . C23 C 0.99929(16) 0.0851(2) 0.6608(4) 0.0271(6) Uani 1 1 d . . . H23 H 0.9908 0.0664 0.5308 0.047(12) Uiso 1 1 calc R . . C24 C 0.94545(14) 0.09039(17) 0.7670(4) 0.0221(5) Uani 1 1 d . . . H24 H 0.9001 0.0755 0.7085 0.023(8) Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Zn1 0.01607(13) 0.01404(12) 0.01531(13) 0.00024(10) 0.00342(9) 0.00010(11) Cl1 0.0302(4) 0.0160(2) 0.0216(3) -0.0010(2) 0.0083(3) 0.0021(2) Cl2 0.0214(3) 0.0149(2) 0.0191(3) 0.0028(2) 0.0042(2) 0.0006(2) N1 0.0134(9) 0.0139(9) 0.0163(10) 0.0005(7) 0.0035(8) -0.0001(8) N2 0.0146(10) 0.0153(9) 0.0160(10) 0.0021(7) 0.0025(8) 0.0016(7) C1 0.0154(11) 0.0159(11) 0.0294(13) 0.0043(10) -0.0008(10) 0.0008(9) C2 0.0170(11) 0.0183(11) 0.0201(12) 0.0032(9) 0.0021(9) 0.0037(9) C3 0.0173(11) 0.0206(12) 0.0186(12) 0.0045(9) 0.0040(9) 0.0053(9) C4 0.0295(14) 0.0128(12) 0.0248(13) 0.0030(10) 0.0097(11) 0.0063(10) C5 0.0307(13) 0.0132(11) 0.0231(12) -0.0002(9) 0.0094(10) -0.0002(10) C6 0.0201(12) 0.0175(11) 0.0227(13) -0.0014(9) 0.0067(10) -0.0046(9) C7 0.0176(11) 0.0180(11) 0.0228(12) -0.0012(9) 0.0041(9) -0.0028(9) C8 0.0178(12) 0.0169(12) 0.0281(14) -0.0009(10) 0.0033(10) 0.0006(10) C9 0.0202(12) 0.0279(13) 0.0127(11) -0.0061(9) 0.0018(9) 0.0062(10) C10 0.0156(11) 0.0169(11) 0.0169(11) 0.0033(9) 0.0015(9) 0.0024(9) C11 0.0169(11) 0.0154(11) 0.0183(12) -0.0008(9) 0.0032(9) -0.0021(9) C12 0.0177(12) 0.0181(11) 0.0206(12) 0.0013(9) 0.0048(9) -0.0035(9) C13 0.0197(13) 0.0359(14) 0.0234(13) 0.0018(11) 0.0006(10) -0.0093(11) C14 0.0175(13) 0.052(2) 0.0343(16) 0.0079(14) 0.0022(12) -0.0101(13) C15 0.0201(14) 0.0412(17) 0.0383(18) 0.0006(13) 0.0111(12) -0.0043(12) C16 0.0288(16) 0.0418(17) 0.0239(15) -0.0038(12) 0.0128(12) -0.0049(13) C17 0.0195(12) 0.0356(15) 0.0209(13) -0.0053(11) 0.0043(10) -0.0040(11) C18 0.0168(12) 0.0154(11) 0.0230(12) 0.0017(9) 0.0059(9) 0.0030(9) C19 0.0152(11) 0.0151(10) 0.0227(12) 0.0005(9) 0.0042(9) 0.0025(9) C20 0.0181(12) 0.0264(13) 0.0227(14) -0.0035(10) 0.0013(10) 0.0015(10) C21 0.0152(12) 0.0314(14) 0.0363(16) -0.0034(12) 0.0035(11) 0.0015(10) C22 0.0247(14) 0.0335(15) 0.0329(16) 0.0005(12) 0.0127(12) 0.0051(12) C23 0.0295(15) 0.0320(15) 0.0199(13) -0.0046(10) 0.0046(11) 0.0056(11) C24 0.0185(12) 0.0225(12) 0.0246(13) -0.0042(10) 0.0009(10) 0.0012(9) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Zn1 N2 2.113(2) . ? Zn1 N1 2.125(2) . ? Zn1 Cl1 2.1938(7) . ? Zn1 Cl2 2.2425(6) . ? N1 C1 1.505(3) . ? N1 C11 1.507(3) . ? N1 C9 1.509(3) . ? N2 C10 1.494(3) . ? N2 C8 1.505(3) . ? N2 C18 1.512(3) . ? C1 C2 1.465(4) . ? C1 H1A 0.9900 . ? C1 H1B 0.9900 . ? C2 C3 1.191(4) . ? C3 C4 1.437(4) . ? C4 C5 1.323(4) . ? C4 H4 0.9500 . ? C5 C6 1.423(4) . ? C5 H5 0.9500 . ? C6 C7 1.201(4) . ? C7 C8 1.456(4) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 C10 1.517(4) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 C12 1.511(4) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 C17 1.395(4) . ? C12 C13 1.397(4) . ? C13 C14 1.397(4) . ? C13 H13 0.9500 . ? C14 C15 1.373(5) . ? C14 H14 0.9500 . ? C15 C16 1.396(5) . ? C15 H15 0.9500 . ? C16 C17 1.385(4) . ? C16 H16 0.9500 . ? C17 H17 0.9500 . ? C18 C19 1.515(3) . ? C18 H18A 0.9900 . ? C18 H18B 0.9900 . ? C19 C24 1.391(4) . ? C19 C20 1.396(4) . ? C20 C21 1.386(4) . ? C20 H20 0.9500 . ? C21 C22 1.381(5) . ? C21 H21 0.9500 . ? C22 C23 1.402(4) . ? C22 H22 0.9500 . ? C23 C24 1.393(4) . ? C23 H23 0.9500 . ? C24 H24 0.9500 . ? 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 Zn1 N1 89.18(8) . . ? N2 Zn1 Cl1 119.92(6) . . ? N1 Zn1 Cl1 117.72(6) . . ? N2 Zn1 Cl2 105.76(6) . . ? N1 Zn1 Cl2 109.10(6) . . ? Cl1 Zn1 Cl2 112.54(3) . . ? C1 N1 C11 107.27(19) . . ? C1 N1 C9 111.2(2) . . ? C11 N1 C9 106.82(19) . . ? C1 N1 Zn1 117.86(16) . . ? C11 N1 Zn1 112.92(15) . . ? C9 N1 Zn1 100.22(14) . . ? C10 N2 C8 110.8(2) . . ? C10 N2 C18 112.4(2) . . ? C8 N2 C18 108.3(2) . . ? C10 N2 Zn1 101.99(15) . . ? C8 N2 Zn1 114.13(16) . . ? C18 N2 Zn1 109.21(15) . . ? C2 C1 N1 115.2(2) . . ? C2 C1 H1A 108.5 . . ? N1 C1 H1A 108.5 . . ? C2 C1 H1B 108.5 . . ? N1 C1 H1B 108.5 . . ? H1A C1 H1B 107.5 . . ? C3 C2 C1 174.2(3) . . ? C2 C3 C4 173.5(3) . . ? C5 C4 C3 121.2(2) . . ? C5 C4 H4 119.4 . . ? C3 C4 H4 119.4 . . ? C4 C5 C6 120.8(3) . . ? C4 C5 H5 119.6 . . ? C6 C5 H5 119.6 . . ? C7 C6 C5 171.4(3) . . ? C6 C7 C8 174.8(3) . . ? C7 C8 N2 112.9(2) . . ? C7 C8 H8A 109.0 . . ? N2 C8 H8A 109.0 . . ? C7 C8 H8B 109.0 . . ? N2 C8 H8B 109.0 . . ? H8A C8 H8B 107.8 . . ? N1 C9 C10 113.7(2) . . ? N1 C9 H9A 108.8 . . ? C10 C9 H9A 108.8 . . ? N1 C9 H9B 108.8 . . ? C10 C9 H9B 108.8 . . ? H9A C9 H9B 107.7 . . ? N2 C10 C9 110.2(2) . . ? N2 C10 H10A 109.6 . . ? C9 C10 H10A 109.6 . . ? N2 C10 H10B 109.6 . . ? C9 C10 H10B 109.6 . . ? H10A C10 H10B 108.1 . . ? N1 C11 C12 114.7(2) . . ? N1 C11 H11A 108.6 . . ? C12 C11 H11A 108.6 . . ? N1 C11 H11B 108.6 . . ? C12 C11 H11B 108.6 . . ? H11A C11 H11B 107.6 . . ? C17 C12 C13 118.4(3) . . ? C17 C12 C11 122.7(2) . . ? C13 C12 C11 118.9(2) . . ? C14 C13 C12 120.5(3) . . ? C14 C13 H13 119.7 . . ? C12 C13 H13 119.7 . . ? C15 C14 C13 120.6(3) . . ? C15 C14 H14 119.7 . . ? C13 C14 H14 119.7 . . ? C14 C15 C16 119.3(3) . . ? C14 C15 H15 120.4 . . ? C16 C15 H15 120.4 . . ? C17 C16 C15 120.5(3) . . ? C17 C16 H16 119.8 . . ? C15 C16 H16 119.8 . . ? C16 C17 C12 120.8(3) . . ? C16 C17 H17 119.6 . . ? C12 C17 H17 119.6 . . ? N2 C18 C19 115.6(2) . . ? N2 C18 H18A 108.4 . . ? C19 C18 H18A 108.4 . . ? N2 C18 H18B 108.4 . . ? C19 C18 H18B 108.4 . . ? H18A C18 H18B 107.4 . . ? C24 C19 C20 118.8(2) . . ? C24 C19 C18 121.1(2) . . ? C20 C19 C18 120.1(2) . . ? C21 C20 C19 120.8(3) . . ? C21 C20 H20 119.6 . . ? C19 C20 H20 119.6 . . ? C22 C21 C20 120.3(3) . . ? C22 C21 H21 119.9 . . ? C20 C21 H21 119.9 . . ? C21 C22 C23 119.8(3) . . ? C21 C22 H22 120.1 . . ? C23 C22 H22 120.1 . . ? C24 C23 C22 119.6(3) . . ? C24 C23 H23 120.2 . . ? C22 C23 H23 120.2 . . ? C19 C24 C23 120.7(2) . . ? C19 C24 H24 119.6 . . ? C23 C24 H24 119.6 . . ? 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 N2 Zn1 N1 C1 -109.48(18) . . . . ? Cl1 Zn1 N1 C1 14.30(19) . . . . ? Cl2 Zn1 N1 C1 144.11(16) . . . . ? N2 Zn1 N1 C11 124.50(16) . . . . ? Cl1 Zn1 N1 C11 -111.72(15) . . . . ? Cl2 Zn1 N1 C11 18.08(17) . . . . ? N2 Zn1 N1 C9 11.20(15) . . . . ? Cl1 Zn1 N1 C9 134.98(13) . . . . ? Cl2 Zn1 N1 C9 -95.21(14) . . . . ? N1 Zn1 N2 C10 16.37(15) . . . . ? Cl1 Zn1 N2 C10 -105.53(14) . . . . ? Cl2 Zn1 N2 C10 126.01(13) . . . . ? N1 Zn1 N2 C8 135.89(17) . . . . ? Cl1 Zn1 N2 C8 13.99(19) . . . . ? Cl2 Zn1 N2 C8 -114.47(16) . . . . ? N1 Zn1 N2 C18 -102.74(16) . . . . ? Cl1 Zn1 N2 C18 135.36(14) . . . . ? Cl2 Zn1 N2 C18 6.90(17) . . . . ? C11 N1 C1 C2 174.0(2) . . . . ? C9 N1 C1 C2 -69.5(3) . . . . ? Zn1 N1 C1 C2 45.3(3) . . . . ? N1 C1 C2 C3 -140(3) . . . . ? C1 C2 C3 C4 123(3) . . . . ? C2 C3 C4 C5 16(3) . . . . ? C3 C4 C5 C6 2.0(4) . . . . ? C4 C5 C6 C7 -1(2) . . . . ? C5 C6 C7 C8 48(4) . . . . ? C6 C7 C8 N2 -47(3) . . . . ? C10 N2 C8 C7 52.8(3) . . . . ? C18 N2 C8 C7 176.5(2) . . . . ? Zn1 N2 C8 C7 -61.6(3) . . . . ? C1 N1 C9 C10 86.6(3) . . . . ? C11 N1 C9 C10 -156.7(2) . . . . ? Zn1 N1 C9 C10 -38.8(2) . . . . ? C8 N2 C10 C9 -163.4(2) . . . . ? C18 N2 C10 C9 75.2(3) . . . . ? Zn1 N2 C10 C9 -41.6(2) . . . . ? N1 C9 C10 N2 59.1(3) . . . . ? C1 N1 C11 C12 -49.9(3) . . . . ? C9 N1 C11 C12 -169.2(2) . . . . ? Zn1 N1 C11 C12 81.6(2) . . . . ? N1 C11 C12 C17 -60.9(3) . . . . ? N1 C11 C12 C13 119.2(3) . . . . ? C17 C12 C13 C14 -0.2(4) . . . . ? C11 C12 C13 C14 179.8(3) . . . . ? C12 C13 C14 C15 1.1(5) . . . . ? C13 C14 C15 C16 -0.9(5) . . . . ? C14 C15 C16 C17 -0.1(5) . . . . ? C15 C16 C17 C12 1.0(5) . . . . ? C13 C12 C17 C16 -0.9(4) . . . . ? C11 C12 C17 C16 179.2(3) . . . . ? C10 N2 C18 C19 63.8(3) . . . . ? C8 N2 C18 C19 -59.0(3) . . . . ? Zn1 N2 C18 C19 176.20(18) . . . . ? N2 C18 C19 C24 -86.8(3) . . . . ? N2 C18 C19 C20 95.4(3) . . . . ? C24 C19 C20 C21 1.8(4) . . . . ? C18 C19 C20 C21 179.6(3) . . . . ? C19 C20 C21 C22 -0.1(5) . . . . ? C20 C21 C22 C23 -1.9(5) . . . . ? C21 C22 C23 C24 2.2(5) . . . . ? C20 C19 C24 C23 -1.5(4) . . . . ? C18 C19 C24 C23 -179.3(3) . . . . ? C22 C23 C24 C19 -0.5(4) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.51 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 1.587 _refine_diff_density_min -0.246 _refine_diff_density_rms 0.090 data_02023 _database_code_CSD 204065 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C24 H24 Cl2 Cu N2' _chemical_formula_sum 'C24 H24 Cl2 Cu N2' _chemical_formula_weight 474.89 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' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P2(1)/c 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 9.8606(2) _cell_length_b 18.1537(4) _cell_length_c 13.0210(3) _cell_angle_alpha 90.00 _cell_angle_beta 110.0930(10) _cell_angle_gamma 90.00 _cell_volume 2188.98(8) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 9160 _cell_measurement_theta_min 3.14 _cell_measurement_theta_max 39.98 _exptl_crystal_description plate _exptl_crystal_colour blue _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.441 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 980 _exptl_absorpt_coefficient_mu 1.255 _exptl_absorpt_correction_type multi-scans _exptl_absorpt_correction_T_min 0.7875 _exptl_absorpt_correction_T_max 0.9515 _exptl_absorpt_process_details 'SADABS, R. Blessing (1995)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_details '0.30 degree frames measured for 20 seconds each' _diffrn_measurement_method \w-scans _diffrn_measurement_device 'three-circle goniometer with fixed chi' _diffrn_measurement_device_type 'Bruker Platform goniometer' _diffrn_detector 'CCD area detector' _diffrn_detector_type 'Bruker SMART 6000' _diffrn_detector_area_resol_mean 44.52 _diffrn_standards_number 668 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 572 _diffrn_standards_decay_% 0.0 _diffrn_reflns_number 49732 _diffrn_reflns_av_R_equivalents 0.0283 _diffrn_reflns_av_sigmaI/netI 0.0279 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -32 _diffrn_reflns_limit_k_max 32 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 2.01 _diffrn_reflns_theta_max 40.01 _reflns_number_total 13463 _reflns_number_gt 10890 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 1999)' _computing_cell_refinement 'SAINT (Bruker, 1999)' _computing_data_reduction 'SAINT (Bruker, 1999)' _computing_structure_solution 'SIR-92 (Alatomare et al., 1993)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'XTEL (local library)' _computing_publication_material 'XCIF (Bruker, 1999), XTEL (local library)' _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^)+(0.0426P)^2^+0.3868P] 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 riding _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 13463 _refine_ls_number_parameters 286 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0425 _refine_ls_R_factor_gt 0.0296 _refine_ls_wR_factor_ref 0.0835 _refine_ls_wR_factor_gt 0.0770 _refine_ls_goodness_of_fit_ref 1.032 _refine_ls_restrained_S_all 1.032 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu 0.335501(10) 0.144363(5) 0.118805(8) 0.01346(2) Uani 1 1 d . . . Cl1 Cl 0.18425(2) 0.220408(12) -0.004875(16) 0.01931(4) Uani 1 1 d . . . Cl2 Cl 0.41740(3) 0.093189(12) -0.004288(17) 0.02169(4) Uani 1 1 d . . . N1 N 0.30867(7) 0.20464(4) 0.24566(6) 0.01523(11) Uani 1 1 d . . . N2 N 0.44169(8) 0.06815(4) 0.23816(6) 0.01516(10) Uani 1 1 d . . . C1 C 0.15071(9) 0.21522(5) 0.22827(7) 0.01987(14) Uani 1 1 d . . . H1A H 0.1413 0.2334 0.2972 0.029(4) Uiso 1 1 calc R . . H1B H 0.1116 0.2537 0.1719 0.023(3) Uiso 1 1 calc R . . C2 C 0.06369(9) 0.14880(6) 0.19451(7) 0.02156(15) Uani 1 1 d . . . C3 C -0.01440(10) 0.09629(6) 0.16298(8) 0.02446(17) Uani 1 1 d . . . C4 C -0.09266(11) 0.02937(7) 0.12773(8) 0.0284(2) Uani 1 1 d . . . H4 H -0.1944 0.0289 0.1107 0.031(4) Uiso 1 1 calc R . . C5 C -0.02419(12) -0.03300(7) 0.11829(8) 0.0292(2) Uani 1 1 d . . . H5 H -0.0773 -0.0773 0.0953 0.043(5) Uiso 1 1 calc R . . C6 C 0.12799(12) -0.03253(6) 0.14284(8) 0.02546(18) Uani 1 1 d . . . C7 C 0.25593(11) -0.02467(5) 0.16451(8) 0.02286(16) Uani 1 1 d . . . C8 C 0.41061(10) -0.01020(5) 0.20069(7) 0.01996(14) Uani 1 1 d . . . H8A H 0.4467 -0.0196 0.1397 0.025(3) Uiso 1 1 calc R . . H8B H 0.4616 -0.0439 0.2615 0.040(5) Uiso 1 1 calc R . . C9 C 0.38225(9) 0.16401(5) 0.35016(6) 0.01709(13) Uani 1 1 d . . . H9A H 0.3300 0.1729 0.4017 0.023(3) Uiso 1 1 calc R . . H9B H 0.4820 0.1827 0.3841 0.016(3) Uiso 1 1 calc R . . C10 C 0.38625(9) 0.08228(5) 0.32919(7) 0.01702(13) Uani 1 1 d . . . H10A H 0.4493 0.0575 0.3963 0.017(3) Uiso 1 1 calc R . . H10B H 0.2878 0.0615 0.3104 0.021(3) Uiso 1 1 calc R . . C11 C 0.37036(9) 0.28156(5) 0.25240(7) 0.01855(13) Uani 1 1 d . . . H11A H 0.3147 0.3092 0.1857 0.024(3) Uiso 1 1 calc R . . H11B H 0.3589 0.3074 0.3159 0.017(3) Uiso 1 1 calc R . . C12 C 0.52740(9) 0.28178(4) 0.26369(7) 0.01730(13) Uani 1 1 d . . . C13 C 0.56852(10) 0.27051(5) 0.17214(8) 0.02112(15) Uani 1 1 d . . . H13 H 0.4969 0.2655 0.1017 0.023(3) Uiso 1 1 calc R . . C14 C 0.71420(12) 0.26659(6) 0.18412(9) 0.02741(18) Uani 1 1 d . . . H14 H 0.7417 0.2584 0.1219 0.046(5) Uiso 1 1 calc R . . C15 C 0.81943(11) 0.27458(7) 0.28655(10) 0.0288(2) Uani 1 1 d . . . H15 H 0.9186 0.2708 0.2944 0.047(5) Uiso 1 1 calc R . . C16 C 0.78027(10) 0.28800(6) 0.37749(9) 0.02526(17) Uani 1 1 d . . . H16 H 0.8524 0.2946 0.4473 0.037(4) Uiso 1 1 calc R . . C17 C 0.63473(10) 0.29182(5) 0.36599(8) 0.02042(14) Uani 1 1 d . . . H17 H 0.6080 0.3013 0.4282 0.023(3) Uiso 1 1 calc R . . C18 C 0.60172(9) 0.08251(5) 0.26927(7) 0.01732(13) Uani 1 1 d . . . H18A H 0.6309 0.0708 0.2055 0.022(3) Uiso 1 1 calc R . . H18B H 0.6192 0.1357 0.2847 0.023(3) Uiso 1 1 calc R . . C19 C 0.69753(9) 0.03987(5) 0.36657(7) 0.01886(14) Uani 1 1 d . . . C20 C 0.73909(11) 0.07078(7) 0.47097(8) 0.02672(18) Uani 1 1 d . . . H20 H 0.7071 0.1189 0.4803 0.035(4) Uiso 1 1 calc R . . C21 C 0.82692(12) 0.03197(9) 0.56158(9) 0.0357(3) Uani 1 1 d . . . H21 H 0.8546 0.0536 0.6323 0.040(4) Uiso 1 1 calc R . . C22 C 0.87390(12) -0.03806(8) 0.54867(10) 0.0373(3) Uani 1 1 d . . . H22 H 0.9326 -0.0649 0.6107 0.054(5) Uiso 1 1 calc R . . C23 C 0.83537(11) -0.06924(6) 0.44526(11) 0.0340(3) Uani 1 1 d . . . H23 H 0.8685 -0.1172 0.4365 0.046(5) Uiso 1 1 calc R . . C24 C 0.74804(10) -0.03026(5) 0.35415(9) 0.02483(17) Uani 1 1 d . . . H24 H 0.7228 -0.0515 0.2834 0.036(4) Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.01528(4) 0.01325(4) 0.01253(4) -0.00050(3) 0.00565(3) -0.00012(3) Cl1 0.01962(8) 0.02067(8) 0.01583(7) 0.00229(6) 0.00375(6) 0.00183(6) Cl2 0.03004(10) 0.02123(9) 0.01822(8) 0.00038(6) 0.01396(7) 0.00417(7) N1 0.0134(2) 0.0163(3) 0.0156(2) -0.0024(2) 0.0045(2) 0.0000(2) N2 0.0182(3) 0.0136(2) 0.0153(2) 0.0000(2) 0.0078(2) -0.0006(2) C1 0.0135(3) 0.0261(4) 0.0198(3) -0.0055(3) 0.0056(2) 0.0009(3) C2 0.0156(3) 0.0317(4) 0.0177(3) -0.0018(3) 0.0061(3) -0.0022(3) C3 0.0182(3) 0.0362(5) 0.0191(3) -0.0014(3) 0.0065(3) -0.0055(3) C4 0.0219(4) 0.0411(6) 0.0218(4) -0.0028(4) 0.0072(3) -0.0140(4) C5 0.0288(4) 0.0356(5) 0.0210(4) -0.0030(3) 0.0059(3) -0.0166(4) C6 0.0304(4) 0.0249(4) 0.0201(4) -0.0029(3) 0.0074(3) -0.0095(3) C7 0.0299(4) 0.0182(3) 0.0202(3) -0.0017(3) 0.0083(3) -0.0058(3) C8 0.0259(4) 0.0137(3) 0.0210(3) -0.0003(3) 0.0091(3) -0.0011(3) C9 0.0167(3) 0.0203(3) 0.0141(3) -0.0020(2) 0.0051(2) -0.0004(2) C10 0.0185(3) 0.0192(3) 0.0149(3) 0.0007(2) 0.0078(2) -0.0014(2) C11 0.0159(3) 0.0156(3) 0.0219(3) -0.0040(3) 0.0037(3) 0.0010(2) C12 0.0163(3) 0.0137(3) 0.0202(3) -0.0018(2) 0.0040(2) -0.0005(2) C13 0.0214(3) 0.0204(4) 0.0212(3) -0.0010(3) 0.0067(3) -0.0031(3) C14 0.0250(4) 0.0309(5) 0.0301(5) -0.0040(4) 0.0144(4) -0.0048(3) C15 0.0176(4) 0.0332(5) 0.0363(5) -0.0047(4) 0.0101(3) -0.0022(3) C16 0.0167(3) 0.0274(4) 0.0279(4) -0.0038(3) 0.0028(3) -0.0019(3) C17 0.0183(3) 0.0192(3) 0.0218(3) -0.0044(3) 0.0044(3) -0.0017(3) C18 0.0177(3) 0.0163(3) 0.0193(3) 0.0030(2) 0.0082(2) 0.0015(2) C19 0.0179(3) 0.0197(3) 0.0191(3) 0.0037(3) 0.0064(3) -0.0001(3) C20 0.0217(4) 0.0384(5) 0.0200(4) -0.0013(3) 0.0071(3) -0.0004(4) C21 0.0226(4) 0.0644(8) 0.0189(4) 0.0075(4) 0.0056(3) -0.0043(5) C22 0.0211(4) 0.0524(7) 0.0334(5) 0.0256(5) 0.0028(4) -0.0055(4) C23 0.0221(4) 0.0241(4) 0.0468(6) 0.0167(4) 0.0005(4) -0.0014(3) C24 0.0218(4) 0.0183(4) 0.0301(4) 0.0047(3) 0.0034(3) 0.0014(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 N1 2.0726(7) . ? Cu1 N2 2.0755(7) . ? Cu1 Cl2 2.2301(2) . ? Cu1 Cl1 2.2524(2) . ? N1 C9 1.4978(11) . ? N1 C1 1.5073(10) . ? N1 C11 1.5137(11) . ? N2 C10 1.4882(11) . ? N2 C8 1.5008(11) . ? N2 C18 1.5109(11) . ? C1 C2 1.4575(13) . ? C1 H1A 0.9900 . ? C1 H1B 0.9900 . ? C2 C3 1.2054(14) . ? C3 C4 1.4278(15) . ? C4 C5 1.3454(18) . ? C4 H4 0.9500 . ? C5 C6 1.4227(16) . ? C5 H5 0.9500 . ? C6 C7 1.2029(15) . ? C7 C8 1.4573(14) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 C10 1.5117(12) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 C12 1.5044(12) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 C13 1.3997(13) . ? C12 C17 1.3998(12) . ? C13 C14 1.3924(14) . ? C13 H13 0.9500 . ? C14 C15 1.3877(16) . ? C14 H14 0.9500 . ? C15 C16 1.3874(16) . ? C15 H15 0.9500 . ? C16 C17 1.3925(13) . ? C16 H16 0.9500 . ? C17 H17 0.9500 . ? C18 C19 1.5082(12) . ? C18 H18A 0.9900 . ? C18 H18B 0.9900 . ? C19 C20 1.3957(14) . ? C19 C24 1.3964(14) . ? C20 C21 1.3916(16) . ? C20 H20 0.9500 . ? C21 C22 1.383(2) . ? C21 H21 0.9500 . ? C22 C23 1.388(2) . ? C22 H22 0.9500 . ? C23 C24 1.3956(14) . ? C23 H23 0.9500 . ? C24 H24 0.9500 . ? 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 Cu1 N2 85.69(3) . . ? N1 Cu1 Cl2 165.82(2) . . ? N2 Cu1 Cl2 92.66(2) . . ? N1 Cu1 Cl1 90.68(2) . . ? N2 Cu1 Cl1 169.65(2) . . ? Cl2 Cu1 Cl1 93.197(9) . . ? C9 N1 C1 110.63(7) . . ? C9 N1 C11 110.00(6) . . ? C1 N1 C11 105.37(6) . . ? C9 N1 Cu1 108.03(5) . . ? C1 N1 Cu1 110.84(5) . . ? C11 N1 Cu1 111.99(5) . . ? C10 N2 C8 109.41(6) . . ? C10 N2 C18 113.10(6) . . ? C8 N2 C18 109.18(7) . . ? C10 N2 Cu1 104.63(5) . . ? C8 N2 Cu1 113.22(5) . . ? C18 N2 Cu1 107.31(5) . . ? C2 C1 N1 114.25(7) . . ? C2 C1 H1A 108.7 . . ? N1 C1 H1A 108.7 . . ? C2 C1 H1B 108.7 . . ? N1 C1 H1B 108.7 . . ? H1A C1 H1B 107.6 . . ? C3 C2 C1 176.37(11) . . ? C2 C3 C4 173.64(11) . . ? C5 C4 C3 120.84(9) . . ? C5 C4 H4 119.6 . . ? C3 C4 H4 119.6 . . ? C4 C5 C6 119.88(9) . . ? C4 C5 H5 120.1 . . ? C6 C5 H5 120.1 . . ? C7 C6 C5 173.49(12) . . ? C6 C7 C8 173.78(10) . . ? C7 C8 N2 110.49(7) . . ? C7 C8 H8A 109.6 . . ? N2 C8 H8A 109.6 . . ? C7 C8 H8B 109.6 . . ? N2 C8 H8B 109.6 . . ? H8A C8 H8B 108.1 . . ? N1 C9 C10 110.72(6) . . ? N1 C9 H9A 109.5 . . ? C10 C9 H9A 109.5 . . ? N1 C9 H9B 109.5 . . ? C10 C9 H9B 109.5 . . ? H9A C9 H9B 108.1 . . ? N2 C10 C9 110.64(7) . . ? N2 C10 H10A 109.5 . . ? C9 C10 H10A 109.5 . . ? N2 C10 H10B 109.5 . . ? C9 C10 H10B 109.5 . . ? H10A C10 H10B 108.1 . . ? C12 C11 N1 112.82(7) . . ? C12 C11 H11A 109.0 . . ? N1 C11 H11A 109.0 . . ? C12 C11 H11B 109.0 . . ? N1 C11 H11B 109.0 . . ? H11A C11 H11B 107.8 . . ? C13 C12 C17 118.95(8) . . ? C13 C12 C11 120.40(7) . . ? C17 C12 C11 120.64(8) . . ? C14 C13 C12 120.10(9) . . ? C14 C13 H13 119.9 . . ? C12 C13 H13 119.9 . . ? C15 C14 C13 120.29(10) . . ? C15 C14 H14 119.9 . . ? C13 C14 H14 119.9 . . ? C16 C15 C14 120.21(9) . . ? C16 C15 H15 119.9 . . ? C14 C15 H15 119.9 . . ? C15 C16 C17 119.72(9) . . ? C15 C16 H16 120.1 . . ? C17 C16 H16 120.1 . . ? C16 C17 C12 120.68(9) . . ? C16 C17 H17 119.7 . . ? C12 C17 H17 119.7 . . ? C19 C18 N2 115.58(7) . . ? C19 C18 H18A 108.4 . . ? N2 C18 H18A 108.4 . . ? C19 C18 H18B 108.4 . . ? N2 C18 H18B 108.4 . . ? H18A C18 H18B 107.4 . . ? C20 C19 C24 118.84(9) . . ? C20 C19 C18 120.09(9) . . ? C24 C19 C18 121.06(8) . . ? C21 C20 C19 120.73(11) . . ? C21 C20 H20 119.6 . . ? C19 C20 H20 119.6 . . ? C22 C21 C20 119.96(11) . . ? C22 C21 H21 120.0 . . ? C20 C21 H21 120.0 . . ? C21 C22 C23 120.09(10) . . ? C21 C22 H22 120.0 . . ? C23 C22 H22 120.0 . . ? C22 C23 C24 120.08(11) . . ? C22 C23 H23 120.0 . . ? C24 C23 H23 120.0 . . ? C23 C24 C19 120.28(11) . . ? C23 C24 H24 119.9 . . ? C19 C24 H24 119.9 . . ? 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 N2 Cu1 N1 C9 2.22(5) . . . . ? Cl2 Cu1 N1 C9 -81.55(10) . . . . ? Cl1 Cu1 N1 C9 172.52(5) . . . . ? N2 Cu1 N1 C1 -119.13(6) . . . . ? Cl2 Cu1 N1 C1 157.10(7) . . . . ? Cl1 Cu1 N1 C1 51.17(6) . . . . ? N2 Cu1 N1 C11 123.51(5) . . . . ? Cl2 Cu1 N1 C11 39.74(12) . . . . ? Cl1 Cu1 N1 C11 -66.19(5) . . . . ? N1 Cu1 N2 C10 22.85(5) . . . . ? Cl2 Cu1 N2 C10 -171.25(5) . . . . ? Cl1 Cu1 N2 C10 -46.86(14) . . . . ? N1 Cu1 N2 C8 141.92(6) . . . . ? Cl2 Cu1 N2 C8 -52.19(5) . . . . ? Cl1 Cu1 N2 C8 72.21(13) . . . . ? N1 Cu1 N2 C18 -97.55(5) . . . . ? Cl2 Cu1 N2 C18 68.34(5) . . . . ? Cl1 Cu1 N2 C18 -167.26(9) . . . . ? C9 N1 C1 C2 -74.59(9) . . . . ? C11 N1 C1 C2 166.57(8) . . . . ? Cu1 N1 C1 C2 45.22(9) . . . . ? N1 C1 C2 C3 -143.8(16) . . . . ? C1 C2 C3 C4 151.9(13) . . . . ? C2 C3 C4 C5 -6.0(10) . . . . ? C3 C4 C5 C6 -0.48(16) . . . . ? C4 C5 C6 C7 -7.5(10) . . . . ? C5 C6 C7 C8 49.0(16) . . . . ? C6 C7 C8 N2 -39.2(10) . . . . ? C10 N2 C8 C7 58.78(9) . . . . ? C18 N2 C8 C7 -176.96(7) . . . . ? Cu1 N2 C8 C7 -57.49(8) . . . . ? C1 N1 C9 C10 94.13(8) . . . . ? C11 N1 C9 C10 -149.87(7) . . . . ? Cu1 N1 C9 C10 -27.35(8) . . . . ? C8 N2 C10 C9 -166.10(7) . . . . ? C18 N2 C10 C9 71.97(8) . . . . ? Cu1 N2 C10 C9 -44.50(7) . . . . ? N1 C9 C10 N2 49.58(9) . . . . ? C9 N1 C11 C12 63.89(9) . . . . ? C1 N1 C11 C12 -176.84(7) . . . . ? Cu1 N1 C11 C12 -56.25(8) . . . . ? N1 C11 C12 C13 78.96(10) . . . . ? N1 C11 C12 C17 -99.81(9) . . . . ? C17 C12 C13 C14 2.44(14) . . . . ? C11 C12 C13 C14 -176.34(9) . . . . ? C12 C13 C14 C15 -0.66(16) . . . . ? C13 C14 C15 C16 -1.30(17) . . . . ? C14 C15 C16 C17 1.41(17) . . . . ? C15 C16 C17 C12 0.42(15) . . . . ? C13 C12 C17 C16 -2.34(14) . . . . ? C11 C12 C17 C16 176.44(9) . . . . ? C10 N2 C18 C19 56.78(10) . . . . ? C8 N2 C18 C19 -65.29(9) . . . . ? Cu1 N2 C18 C19 171.65(6) . . . . ? N2 C18 C19 C20 -93.25(10) . . . . ? N2 C18 C19 C24 87.78(10) . . . . ? C24 C19 C20 C21 -1.29(15) . . . . ? C18 C19 C20 C21 179.72(9) . . . . ? C19 C20 C21 C22 -0.04(16) . . . . ? C20 C21 C22 C23 0.98(17) . . . . ? C21 C22 C23 C24 -0.58(17) . . . . ? C22 C23 C24 C19 -0.77(16) . . . . ? C20 C19 C24 C23 1.69(15) . . . . ? C18 C19 C24 C23 -179.33(9) . . . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 40.01 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.889 _refine_diff_density_min -0.323 _refine_diff_density_rms 0.079