# Supplementary Material (ESI) for New Journal of Chemistry # This journal is © The Royal Society of Chemistry and # The Centre National de la Recherche Scientifique, 2009 data_global _journal_coden_Cambridge 440 loop_ _publ_author_name 'Jiro Abe' 'Fumiyasu Iwahori' 'Atsushi Kimoto' 'Shimpei Niitsu' _publ_contact_author_name 'Jiro Abe' _publ_contact_author_email JIRO_ABE@CHEM.AOYAMA.AC.JP _publ_section_title ; Formation of hexaarylbiimidazole heterodimers via cross recombination of two lophyl radicals ; # Attachment '1_2.cif' data_prepared _database_code_depnum_ccdc_archive 'CCDC 722513' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C42 H26 Cl4 N4' _chemical_formula_weight 728.47 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pbca loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 16.1217(4) _cell_length_b 12.4587(3) _cell_length_c 34.4958(10) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 6928.7(3) _cell_formula_units_Z 8 _cell_measurement_temperature 103 _cell_measurement_reflns_used 4967 _cell_measurement_theta_min 2.38 _cell_measurement_theta_max 20.65 _exptl_crystal_description needle _exptl_crystal_colour yellow _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.05 _exptl_crystal_density_diffrn 1.397 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2992 _exptl_absorpt_coefficient_mu 0.380 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.8946 _exptl_absorpt_correction_T_max 0.9813 _exptl_absorpt_process_details 'SADABS Sheldrick 1996' _exptl_special_details ; ? ; _diffrn_ambient_temperature 103 _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean 8.333 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 53043 _diffrn_reflns_av_R_equivalents 0.1090 _diffrn_reflns_av_sigmaI/netI 0.0780 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -41 _diffrn_reflns_limit_l_max 37 _diffrn_reflns_theta_min 1.18 _diffrn_reflns_theta_max 25.34 _reflns_number_total 6337 _reflns_number_gt 3821 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0654P)^2^+34.2408P] 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 'no refined H' _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6337 _refine_ls_number_parameters 451 _refine_ls_number_restraints 318 _refine_ls_R_factor_all 0.1329 _refine_ls_R_factor_gt 0.0708 _refine_ls_wR_factor_ref 0.1922 _refine_ls_wR_factor_gt 0.1555 _refine_ls_goodness_of_fit_ref 1.012 _refine_ls_restrained_S_all 1.050 _refine_ls_shift/su_max 0.015 _refine_ls_shift/su_mean 0.003 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 Cl1 Cl 0.13797(8) -0.00092(10) 0.38002(4) 0.0234(3) Uani 1 1 d . . . Cl2 Cl 0.23754(9) -0.10274(11) 0.31229(4) 0.0342(4) Uani 1 1 d . . . Cl3 Cl 0.18365(9) 0.24338(12) 0.22378(4) 0.0340(4) Uani 1 1 d . . . Cl4 Cl -0.07046(12) 0.37393(14) 0.43989(5) 0.0510(5) Uani 1 1 d . . . N2 N -0.0030(3) 0.1674(3) 0.37772(12) 0.0219(5) Uani 1 1 d U . . N3 N 0.1275(2) 0.2401(3) 0.39778(12) 0.0191(5) Uani 1 1 d U . . N4 N 0.0433(2) 0.3381(3) 0.35356(12) 0.0185(5) Uani 1 1 d U . . C1 C -0.0522(3) 0.1060(4) 0.31039(16) 0.0260(5) Uani 1 1 d U . . C2 C 0.1351(3) 0.3413(4) 0.40451(14) 0.0204(5) Uani 1 1 d U . . C3 C -0.1058(3) 0.0519(4) 0.37750(15) 0.0242(5) Uani 1 1 d U . . C4 C 0.1866(3) 0.3786(4) 0.43729(15) 0.0237(5) Uani 1 1 d U . . N1 N -0.0881(3) 0.0752(4) 0.41593(12) 0.0247(5) Uani 1 1 d U . . C5 C 0.1168(3) 0.1725(4) 0.33232(15) 0.0193(5) Uani 1 1 d U . . C6 C 0.0803(3) 0.4032(4) 0.37656(14) 0.0198(5) Uani 1 1 d U . . C7 C 0.1131(3) 0.7031(4) 0.37244(15) 0.0250(6) Uani 1 1 d U . . H7 H 0.1571 0.7538 0.3735 0.030 Uiso 1 1 calc R . . C8 C 0.0659(3) 0.5203(4) 0.37440(15) 0.0216(5) Uani 1 1 d U . . C9 C -0.0676(3) 0.1967(5) 0.28785(16) 0.0278(6) Uani 1 1 d U . . H9 H -0.0764 0.2640 0.3002 0.033 Uiso 1 1 calc R . . C10 C -0.0152(3) 0.5564(4) 0.36907(15) 0.0232(6) Uani 1 1 d U . . H10 H -0.0595 0.5063 0.3677 0.028 Uiso 1 1 calc R . . C11 C 0.1274(3) 0.2245(4) 0.29707(14) 0.0199(6) Uani 1 1 d U . . H11 H 0.1041 0.2938 0.2933 0.024 Uiso 1 1 calc R . . C12 C 0.1949(3) 0.0236(4) 0.30704(15) 0.0206(6) Uani 1 1 d U . . C13 C 0.0700(3) 0.2298(4) 0.36519(15) 0.0194(4) Uani 1 1 d U . . C14 C -0.0269(3) 0.1454(4) 0.41541(16) 0.0257(5) Uani 1 1 d U . . C15 C -0.0704(3) 0.1903(5) 0.24796(16) 0.0302(6) Uani 1 1 d U . . H15 H -0.0817 0.2527 0.2330 0.036 Uiso 1 1 calc R . . C16 C -0.0544(3) 0.1075(4) 0.35324(15) 0.0234(5) Uani 1 1 d U . . C17 C -0.1736(3) -0.0236(4) 0.36881(15) 0.0260(5) Uani 1 1 d U . . C18 C 0.0329(3) 0.7387(4) 0.36758(15) 0.0257(6) Uani 1 1 d U . . H18 H 0.0218 0.8133 0.3654 0.031 Uiso 1 1 calc R . . C19 C 0.1509(3) 0.0704(4) 0.33728(15) 0.0197(6) Uani 1 1 d U . . C20 C -0.1829(3) -0.1150(4) 0.39182(16) 0.0281(6) Uani 1 1 d U . . H20 H -0.1443 -0.1287 0.4121 0.034 Uiso 1 1 calc R . . C21 C 0.1714(3) 0.1765(4) 0.26738(15) 0.0209(6) Uani 1 1 d U . . C22 C -0.0112(4) 0.2864(5) 0.46699(17) 0.0336(6) Uani 1 1 d U . . C23 C 0.2062(3) 0.0753(4) 0.27236(15) 0.0212(6) Uani 1 1 d U . . H23 H 0.2371 0.0426 0.2521 0.025 Uiso 1 1 calc R . . C24 C -0.0403(3) 0.0037(5) 0.25138(16) 0.0312(6) Uani 1 1 d U . . H24 H -0.0297 -0.0625 0.2386 0.037 Uiso 1 1 calc R . . C25 C -0.3036(3) -0.1659(5) 0.35661(16) 0.0300(7) Uani 1 1 d U . . H25 H -0.3486 -0.2138 0.3526 0.036 Uiso 1 1 calc R . . C26 C 0.1306(3) 0.5943(4) 0.37583(15) 0.0233(6) Uani 1 1 d U . . H26 H 0.1862 0.5705 0.3791 0.028 Uiso 1 1 calc R . . C27 C -0.2306(3) -0.0049(5) 0.33905(16) 0.0272(6) Uani 1 1 d U . . H27 H -0.2251 0.0566 0.3229 0.033 Uiso 1 1 calc R . . C28 C -0.0314(3) 0.6658(4) 0.36580(15) 0.0249(6) Uani 1 1 d U . . H28 H -0.0867 0.6903 0.3623 0.030 Uiso 1 1 calc R . . C29 C -0.0569(3) 0.0937(5) 0.22976(17) 0.0315(7) Uani 1 1 d U . . H29 H -0.0590 0.0893 0.2023 0.038 Uiso 1 1 calc R . . C30 C 0.2928(4) 0.3341(5) 0.48397(16) 0.0291(6) Uani 1 1 d U . . H30 H 0.3344 0.2864 0.4931 0.035 Uiso 1 1 calc R . . C31 C 0.0072(4) 0.1868(5) 0.45254(16) 0.0318(6) Uani 1 1 d U . . C32 C -0.2952(3) -0.0768(4) 0.33318(16) 0.0290(6) Uani 1 1 d U . . H32 H -0.3340 -0.0646 0.3129 0.035 Uiso 1 1 calc R . . C33 C 0.2478(3) 0.3086(4) 0.45117(15) 0.0269(6) Uani 1 1 d U . . H33 H 0.2585 0.2432 0.4379 0.032 Uiso 1 1 calc R . . C34 C 0.2774(3) 0.4296(4) 0.50367(16) 0.0294(6) Uani 1 1 d U . . H34 H 0.3081 0.4469 0.5263 0.035 Uiso 1 1 calc R . . C35 C 0.2173(3) 0.4989(5) 0.49006(16) 0.0280(6) Uani 1 1 d U . . H35 H 0.2066 0.5641 0.5035 0.034 Uiso 1 1 calc R . . C36 C 0.1725(3) 0.4742(4) 0.45699(15) 0.0257(6) Uani 1 1 d U . . H36 H 0.1317 0.5229 0.4477 0.031 Uiso 1 1 calc R . . C37 C -0.0387(3) 0.0080(5) 0.29185(16) 0.0288(6) Uani 1 1 d U . . H37 H -0.0286 -0.0550 0.3066 0.035 Uiso 1 1 calc R . . C38 C -0.2476(3) -0.1858(5) 0.38554(16) 0.0299(6) Uani 1 1 d U . . H38 H -0.2531 -0.2481 0.4012 0.036 Uiso 1 1 calc R . . C39 C 0.0595(4) 0.2511(5) 0.52521(18) 0.0391(7) Uani 1 1 d U . . H39 H 0.0781 0.2733 0.5501 0.047 Uiso 1 1 calc R . . C40 C 0.0150(4) 0.3198(5) 0.50348(17) 0.0363(7) Uani 1 1 d U . . H40 H 0.0019 0.3894 0.5128 0.044 Uiso 1 1 calc R . . C41 C 0.0789(4) 0.1486(5) 0.51234(18) 0.0398(7) Uani 1 1 d U . . H41 H 0.1102 0.1024 0.5287 0.048 Uiso 1 1 calc R . . C42 C 0.0539(4) 0.1121(5) 0.47651(17) 0.0368(7) Uani 1 1 d U . . H42 H 0.0665 0.0416 0.4679 0.044 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 Cl1 0.0268(7) 0.0170(6) 0.0264(7) 0.0043(5) -0.0014(6) 0.0008(5) Cl2 0.0362(8) 0.0246(7) 0.0418(9) -0.0054(6) 0.0007(7) 0.0128(6) Cl3 0.0420(8) 0.0398(8) 0.0203(7) 0.0033(6) 0.0112(6) 0.0028(7) Cl4 0.0706(12) 0.0524(11) 0.0301(9) -0.0020(8) 0.0018(8) 0.0306(9) N2 0.0215(8) 0.0252(9) 0.0191(8) -0.0010(8) 0.0002(8) -0.0026(8) N3 0.0187(9) 0.0208(9) 0.0177(10) 0.0005(9) -0.0012(9) -0.0013(9) N4 0.0183(10) 0.0198(9) 0.0174(10) -0.0003(9) -0.0003(9) -0.0005(9) C1 0.0235(10) 0.0324(10) 0.0221(10) -0.0018(9) 0.0007(10) -0.0048(10) C2 0.0205(9) 0.0218(9) 0.0189(9) 0.0001(8) -0.0014(8) -0.0013(8) C3 0.0228(9) 0.0280(9) 0.0218(9) -0.0006(9) 0.0011(9) -0.0034(8) C4 0.0243(10) 0.0251(10) 0.0217(10) 0.0003(9) -0.0034(9) -0.0029(9) N1 0.0248(10) 0.0282(10) 0.0212(10) -0.0004(9) 0.0011(9) -0.0028(9) C5 0.0178(9) 0.0208(10) 0.0193(10) -0.0014(9) -0.0014(9) -0.0018(9) C6 0.0203(9) 0.0206(9) 0.0185(9) -0.0003(8) -0.0004(8) -0.0003(8) C7 0.0286(12) 0.0220(12) 0.0245(12) -0.0008(11) -0.0018(11) -0.0003(11) C8 0.0236(10) 0.0207(10) 0.0206(10) -0.0007(9) -0.0009(9) 0.0003(9) C9 0.0251(12) 0.0353(12) 0.0230(12) -0.0009(11) 0.0003(11) -0.0047(11) C10 0.0253(12) 0.0218(11) 0.0226(12) -0.0011(11) -0.0013(11) 0.0013(10) C11 0.0181(11) 0.0213(11) 0.0201(11) -0.0017(10) -0.0009(10) -0.0017(10) C12 0.0185(12) 0.0217(12) 0.0214(12) -0.0022(11) -0.0011(11) -0.0013(11) C13 0.0188(8) 0.0213(8) 0.0181(8) -0.0004(7) -0.0008(7) -0.0016(7) C14 0.0266(9) 0.0293(9) 0.0211(9) -0.0014(9) 0.0004(9) -0.0020(9) C15 0.0274(12) 0.0389(13) 0.0243(12) -0.0007(12) -0.0001(12) -0.0055(12) C16 0.0219(9) 0.0278(9) 0.0206(9) -0.0011(8) 0.0006(8) -0.0035(8) C17 0.0237(10) 0.0297(10) 0.0246(11) -0.0006(10) 0.0019(9) -0.0040(9) C18 0.0292(12) 0.0224(12) 0.0254(13) -0.0011(11) -0.0020(12) 0.0011(11) C19 0.0180(11) 0.0210(11) 0.0202(11) -0.0016(10) -0.0015(10) -0.0016(10) C20 0.0255(12) 0.0312(12) 0.0276(12) 0.0003(11) 0.0017(11) -0.0051(11) C21 0.0191(12) 0.0226(12) 0.0209(12) -0.0020(11) -0.0002(11) -0.0018(11) C22 0.0367(13) 0.0382(13) 0.0258(12) -0.0031(11) -0.0002(12) -0.0010(12) C23 0.0192(12) 0.0230(12) 0.0215(12) -0.0029(11) 0.0000(11) -0.0011(11) C24 0.0292(13) 0.0390(13) 0.0255(13) -0.0035(12) 0.0008(12) -0.0061(12) C25 0.0271(13) 0.0336(13) 0.0293(13) -0.0008(12) 0.0027(12) -0.0069(12) C26 0.0261(12) 0.0212(11) 0.0226(12) -0.0006(11) -0.0015(11) -0.0001(10) C27 0.0246(12) 0.0314(12) 0.0257(12) -0.0009(11) 0.0027(11) -0.0045(11) C28 0.0273(12) 0.0229(12) 0.0246(12) -0.0012(11) -0.0017(11) 0.0022(11) C29 0.0290(13) 0.0406(13) 0.0250(13) -0.0025(12) 0.0000(12) -0.0066(12) C30 0.0302(13) 0.0306(13) 0.0266(13) 0.0006(11) -0.0068(12) -0.0034(12) C31 0.0346(11) 0.0362(11) 0.0246(11) -0.0031(10) -0.0005(10) -0.0010(10) C32 0.0260(12) 0.0334(13) 0.0276(13) -0.0013(12) 0.0025(12) -0.0057(12) C33 0.0277(12) 0.0281(12) 0.0247(12) 0.0004(11) -0.0054(11) -0.0028(11) C34 0.0309(13) 0.0310(13) 0.0263(13) -0.0002(12) -0.0063(12) -0.0049(12) C35 0.0298(13) 0.0291(13) 0.0252(13) -0.0005(11) -0.0049(11) -0.0049(12) C36 0.0269(12) 0.0269(12) 0.0233(12) -0.0002(11) -0.0037(11) -0.0038(11) C37 0.0267(12) 0.0357(12) 0.0241(12) -0.0026(11) 0.0008(11) -0.0056(11) C38 0.0274(12) 0.0327(13) 0.0296(13) 0.0003(12) 0.0022(12) -0.0066(12) C39 0.0440(14) 0.0440(14) 0.0294(13) -0.0052(12) -0.0026(12) 0.0016(13) C40 0.0402(14) 0.0412(14) 0.0274(13) -0.0042(12) -0.0012(12) -0.0005(13) C41 0.0450(14) 0.0446(14) 0.0298(13) -0.0050(12) -0.0033(12) 0.0028(13) C42 0.0414(13) 0.0417(13) 0.0274(12) -0.0050(11) -0.0023(12) 0.0010(12) _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 Cl1 C19 1.734(5) . ? Cl2 C12 1.727(5) . ? Cl3 C21 1.730(5) . ? Cl4 C22 1.725(6) . ? N2 C14 1.384(7) . ? N2 C16 1.399(6) . ? N2 C13 1.474(6) . ? N3 C2 1.288(6) . ? N3 C13 1.463(6) . ? N4 C6 1.282(6) . ? N4 C13 1.472(6) . ? C1 C9 1.394(8) . ? C1 C37 1.395(8) . ? C1 C16 1.479(7) . ? C2 C4 1.478(7) . ? C2 C6 1.519(7) . ? C3 C16 1.367(7) . ? C3 N1 1.386(7) . ? C3 C17 1.473(7) . ? C4 C36 1.390(7) . ? C4 C33 1.402(7) . ? N1 C14 1.318(7) . ? C5 C11 1.388(7) . ? C5 C19 1.397(7) . ? C5 C13 1.538(7) . ? C6 C8 1.479(7) . ? C7 C18 1.377(7) . ? C7 C26 1.390(7) . ? C7 H7 0.9500 . ? C8 C26 1.393(7) . ? C8 C10 1.394(7) . ? C9 C15 1.379(8) . ? C9 H9 0.9500 . ? C10 C28 1.392(7) . ? C10 H10 0.9500 . ? C11 C21 1.382(7) . ? C11 H11 0.9500 . ? C12 C23 1.371(7) . ? C12 C19 1.389(7) . ? C14 C31 1.487(8) . ? C15 C29 1.374(8) . ? C15 H15 0.9500 . ? C17 C27 1.397(7) . ? C17 C20 1.396(8) . ? C18 C28 1.378(7) . ? C18 H18 0.9500 . ? C20 C38 1.383(8) . ? C20 H20 0.9500 . ? C21 C23 1.390(7) . ? C22 C31 1.370(8) . ? C22 C40 1.391(8) . ? C23 H23 0.9500 . ? C24 C29 1.374(8) . ? C24 C37 1.397(8) . ? C24 H24 0.9500 . ? C25 C38 1.369(8) . ? C25 C32 1.379(8) . ? C25 H25 0.9500 . ? C26 H26 0.9500 . ? C27 C32 1.390(7) . ? C27 H27 0.9500 . ? C28 H28 0.9500 . ? C29 H29 0.9500 . ? C30 C33 1.381(7) . ? C30 C34 1.392(8) . ? C30 H30 0.9500 . ? C31 C42 1.454(8) . ? C32 H32 0.9500 . ? C33 H33 0.9500 . ? C34 C35 1.380(8) . ? C34 H34 0.9500 . ? C35 C36 1.385(7) . ? C35 H35 0.9500 . ? C36 H36 0.9500 . ? C37 H37 0.9500 . ? C38 H38 0.9500 . ? C39 C40 1.344(8) . ? C39 C41 1.387(8) . ? C39 H39 0.9500 . ? C40 H40 0.9500 . ? C41 C42 1.377(8) . ? C41 H41 0.9500 . ? C42 H42 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 C14 N2 C16 107.2(4) . . ? C14 N2 C13 127.1(4) . . ? C16 N2 C13 125.2(4) . . ? C2 N3 C13 106.5(4) . . ? C6 N4 C13 106.0(4) . . ? C9 C1 C37 118.8(5) . . ? C9 C1 C16 122.9(5) . . ? C37 C1 C16 118.3(5) . . ? N3 C2 C4 120.0(5) . . ? N3 C2 C6 109.1(4) . . ? C4 C2 C6 130.8(5) . . ? C16 C3 N1 110.8(5) . . ? C16 C3 C17 130.5(5) . . ? N1 C3 C17 118.7(5) . . ? C36 C4 C33 118.8(5) . . ? C36 C4 C2 123.5(5) . . ? C33 C4 C2 117.5(5) . . ? C14 N1 C3 106.2(4) . . ? C11 C5 C19 118.9(5) . . ? C11 C5 C13 119.3(4) . . ? C19 C5 C13 121.7(4) . . ? N4 C6 C8 121.3(5) . . ? N4 C6 C2 110.0(4) . . ? C8 C6 C2 128.6(4) . . ? C18 C7 C26 121.0(5) . . ? C18 C7 H7 119.5 . . ? C26 C7 H7 119.5 . . ? C26 C8 C10 119.6(5) . . ? C26 C8 C6 122.2(5) . . ? C10 C8 C6 118.2(5) . . ? C15 C9 C1 121.0(5) . . ? C15 C9 H9 119.5 . . ? C1 C9 H9 119.5 . . ? C8 C10 C28 120.2(5) . . ? C8 C10 H10 119.9 . . ? C28 C10 H10 119.9 . . ? C21 C11 C5 120.7(5) . . ? C21 C11 H11 119.6 . . ? C5 C11 H11 119.6 . . ? C23 C12 C19 121.7(5) . . ? C23 C12 Cl2 117.8(4) . . ? C19 C12 Cl2 120.5(4) . . ? N3 C13 N4 108.3(4) . . ? N3 C13 N2 109.0(4) . . ? N4 C13 N2 109.3(4) . . ? N3 C13 C5 107.2(4) . . ? N4 C13 C5 111.6(4) . . ? N2 C13 C5 111.3(4) . . ? N1 C14 N2 110.7(5) . . ? N1 C14 C31 119.7(5) . . ? N2 C14 C31 129.6(5) . . ? C29 C15 C9 120.1(6) . . ? C29 C15 H15 120.0 . . ? C9 C15 H15 120.0 . . ? C3 C16 N2 105.1(4) . . ? C3 C16 C1 128.3(5) . . ? N2 C16 C1 126.6(5) . . ? C27 C17 C20 118.9(5) . . ? C27 C17 C3 122.0(5) . . ? C20 C17 C3 119.0(5) . . ? C7 C18 C28 120.0(5) . . ? C7 C18 H18 120.0 . . ? C28 C18 H18 120.0 . . ? C12 C19 C5 119.4(5) . . ? C12 C19 Cl1 119.0(4) . . ? C5 C19 Cl1 121.6(4) . . ? C38 C20 C17 120.8(5) . . ? C38 C20 H20 119.6 . . ? C17 C20 H20 119.6 . . ? C11 C21 C23 120.5(5) . . ? C11 C21 Cl3 119.6(4) . . ? C23 C21 Cl3 119.9(4) . . ? C31 C22 C40 122.2(6) . . ? C31 C22 Cl4 119.7(5) . . ? C40 C22 Cl4 118.0(5) . . ? C12 C23 C21 118.7(5) . . ? C12 C23 H23 120.6 . . ? C21 C23 H23 120.6 . . ? C29 C24 C37 120.9(6) . . ? C29 C24 H24 119.5 . . ? C37 C24 H24 119.5 . . ? C38 C25 C32 120.6(5) . . ? C38 C25 H25 119.7 . . ? C32 C25 H25 119.7 . . ? C7 C26 C8 119.3(5) . . ? C7 C26 H26 120.3 . . ? C8 C26 H26 120.3 . . ? C32 C27 C17 119.5(5) . . ? C32 C27 H27 120.2 . . ? C17 C27 H27 120.2 . . ? C18 C28 C10 120.0(5) . . ? C18 C28 H28 120.0 . . ? C10 C28 H28 120.0 . . ? C15 C29 C24 119.9(5) . . ? C15 C29 H29 120.1 . . ? C24 C29 H29 120.1 . . ? C33 C30 C34 120.2(5) . . ? C33 C30 H30 119.9 . . ? C34 C30 H30 119.9 . . ? C22 C31 C42 119.0(5) . . ? C22 C31 C14 123.2(5) . . ? C42 C31 C14 117.3(5) . . ? C25 C32 C27 120.4(5) . . ? C25 C32 H32 119.8 . . ? C27 C32 H32 119.8 . . ? C30 C33 C4 120.5(5) . . ? C30 C33 H33 119.8 . . ? C4 C33 H33 119.8 . . ? C35 C34 C30 119.6(5) . . ? C35 C34 H34 120.2 . . ? C30 C34 H34 120.2 . . ? C34 C35 C36 120.5(5) . . ? C34 C35 H35 119.8 . . ? C36 C35 H35 119.8 . . ? C35 C36 C4 120.5(5) . . ? C35 C36 H36 119.7 . . ? C4 C36 H36 119.7 . . ? C24 C37 C1 119.3(6) . . ? C24 C37 H37 120.3 . . ? C1 C37 H37 120.3 . . ? C25 C38 C20 119.7(5) . . ? C25 C38 H38 120.1 . . ? C20 C38 H38 120.1 . . ? C40 C39 C41 121.8(6) . . ? C40 C39 H39 119.1 . . ? C41 C39 H39 119.1 . . ? C39 C40 C22 118.5(6) . . ? C39 C40 H40 120.8 . . ? C22 C40 H40 120.8 . . ? C42 C41 C39 121.7(6) . . ? C42 C41 H41 119.2 . . ? C39 C41 H41 119.2 . . ? C41 C42 C31 116.8(6) . . ? C41 C42 H42 121.6 . . ? C31 C42 H42 121.6 . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.34 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.937 _refine_diff_density_min -1.352 _refine_diff_density_rms 0.098 # Attachment '2_1.cif' data_p21n _database_code_depnum_ccdc_archive 'CCDC 722514' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C42 H26 Cl4 N4' _chemical_formula_weight 728.47 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 12.350(2) _cell_length_b 15.981(3) _cell_length_c 18.000(3) _cell_angle_alpha 90.00 _cell_angle_beta 107.400(2) _cell_angle_gamma 90.00 _cell_volume 3390.0(10) _cell_formula_units_Z 4 _cell_measurement_temperature 103 _cell_measurement_reflns_used 5533 _cell_measurement_theta_min 2.19 _cell_measurement_theta_max 27.18 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_diffrn 1.427 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1496 _exptl_absorpt_coefficient_mu 0.388 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.8924 _exptl_absorpt_correction_T_max 0.9264 _exptl_absorpt_process_details 'SADABS Sheldrick 1996' _exptl_special_details ; ? ; _diffrn_ambient_temperature 103 _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean 8.333 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 18776 _diffrn_reflns_av_R_equivalents 0.0314 _diffrn_reflns_av_sigmaI/netI 0.0414 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 1.74 _diffrn_reflns_theta_max 27.56 _reflns_number_total 7669 _reflns_number_gt 6138 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.1130P)^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 'no refined H' _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 7669 _refine_ls_number_parameters 451 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0584 _refine_ls_R_factor_gt 0.0451 _refine_ls_wR_factor_ref 0.1577 _refine_ls_wR_factor_gt 0.1442 _refine_ls_goodness_of_fit_ref 1.003 _refine_ls_restrained_S_all 1.003 _refine_ls_shift/su_max 0.075 _refine_ls_shift/su_mean 0.017 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 Cl3 Cl 0.14077(4) 0.68526(4) 0.13767(3) 0.02750(15) Uani 1 1 d . . . Cl2 Cl 0.39188(4) 0.62122(3) 0.18798(3) 0.02725(15) Uani 1 1 d . . . Cl4 Cl 0.72186(5) 0.89897(4) 0.15267(3) 0.02929(16) Uani 1 1 d . . . Cl1 Cl 0.26426(5) 0.94860(4) -0.00406(3) 0.02899(16) Uani 1 1 d . . . N4 N 0.61946(14) 0.73330(10) 0.33028(10) 0.0166(4) Uani 1 1 d . . . N3 N 0.54649(13) 0.84509(10) 0.24166(9) 0.0155(3) Uani 1 1 d . . . N2 N 0.59014(14) 0.67396(11) 0.08505(10) 0.0194(4) Uani 1 1 d . . . C8 C 0.24414(17) 0.73923(14) 0.10967(12) 0.0206(4) Uani 1 1 d . . . N1 N 0.64256(13) 0.73156(10) 0.20284(9) 0.0159(3) Uani 1 1 d . . . C10 C 0.37168(17) 0.87682(13) 0.26698(11) 0.0168(4) Uani 1 1 d . . . C11 C 0.55809(17) 0.72232(13) 0.13296(11) 0.0172(4) Uani 1 1 d . . . C12 C 0.47645(16) 0.72363(13) 0.39726(11) 0.0170(4) Uani 1 1 d . . . C13 C 0.47560(17) 0.63653(13) 0.40375(12) 0.0198(4) Uani 1 1 d . . . H13 H 0.5076 0.6027 0.3723 0.024 Uiso 1 1 calc R . . C14 C 0.29924(18) 0.85540(13) 0.04711(11) 0.0206(4) Uani 1 1 d . . . C15 C 0.21449(18) 0.81151(14) 0.06688(12) 0.0214(4) Uani 1 1 d . . . H15 H 0.1383 0.8309 0.0513 0.026 Uiso 1 1 calc R . . C16 C 0.52650(16) 0.76070(12) 0.33968(11) 0.0157(4) Uani 1 1 d . . . C17 C 0.27511(17) 0.83956(14) 0.27750(12) 0.0211(4) Uani 1 1 d . . . H17 H 0.2807 0.7863 0.3018 0.025 Uiso 1 1 calc R . . C18 C 0.84208(16) 0.67270(12) 0.26086(11) 0.0166(4) Uani 1 1 d . . . C19 C 0.73424(16) 0.68362(12) 0.19717(11) 0.0158(4) Uani 1 1 d . . . C20 C 0.48005(16) 0.83123(12) 0.28318(11) 0.0159(4) Uani 1 1 d . . . C21 C 0.44020(17) 0.75557(13) 0.11219(12) 0.0185(4) Uani 1 1 d . . . C22 C 0.74872(16) 0.83770(13) 0.30032(12) 0.0172(4) Uani 1 1 d . . . C23 C 0.36279(18) 0.95614(14) 0.23189(13) 0.0225(5) Uani 1 1 d . . . H23 H 0.4279 0.9822 0.2245 0.027 Uiso 1 1 calc R . . C24 C 0.78512(17) 0.89430(13) 0.25369(12) 0.0205(4) Uani 1 1 d . . . C25 C 0.80816(18) 0.83581(14) 0.37951(12) 0.0220(4) Uani 1 1 d . . . H25 H 0.7864 0.7972 0.4126 0.026 Uiso 1 1 calc R . . C26 C 0.69995(17) 0.64880(13) 0.12367(12) 0.0185(4) Uani 1 1 d . . . C27 C 0.75836(17) 0.59153(13) 0.08407(12) 0.0187(4) Uani 1 1 d . . . C28 C 0.35637(17) 0.71080(13) 0.13230(11) 0.0188(4) Uani 1 1 d . . . C29 C 0.42782(19) 0.59948(15) 0.45643(13) 0.0258(5) Uani 1 1 d . . . H29 H 0.4246 0.5402 0.4596 0.031 Uiso 1 1 calc R . . C30 C 0.41121(17) 0.82798(14) 0.06902(12) 0.0202(4) Uani 1 1 d . . . H30 H 0.4673 0.8589 0.0544 0.024 Uiso 1 1 calc R . . C31 C 0.16242(19) 0.95661(15) 0.21758(13) 0.0274(5) Uani 1 1 d . . . H31 H 0.0907 0.9834 0.1995 0.033 Uiso 1 1 calc R . . C32 C 0.38490(18) 0.64880(15) 0.50435(14) 0.0270(5) Uani 1 1 d . . . H32 H 0.3538 0.6233 0.5410 0.032 Uiso 1 1 calc R . . C33 C 0.43216(17) 0.77280(14) 0.44463(12) 0.0216(4) Uani 1 1 d . . . H33 H 0.4324 0.8320 0.4401 0.026 Uiso 1 1 calc R . . C34 C 0.87530(18) 0.94832(14) 0.28473(14) 0.0264(5) Uani 1 1 d . . . H34 H 0.8984 0.9864 0.2519 0.032 Uiso 1 1 calc R . . C35 C 0.25880(19) 0.99596(14) 0.20815(14) 0.0273(5) Uani 1 1 d . . . H35 H 0.2527 1.0501 0.1854 0.033 Uiso 1 1 calc R . . C36 C 0.8615(2) 0.48450(15) 0.00231(14) 0.0290(5) Uani 1 1 d . . . H36 H 0.8965 0.4477 -0.0250 0.035 Uiso 1 1 calc R . . C37 C 0.71736(18) 0.58489(14) 0.00292(13) 0.0243(5) Uani 1 1 d . . . H37 H 0.6536 0.6173 -0.0248 0.029 Uiso 1 1 calc R . . C38 C 0.38719(19) 0.73525(16) 0.49895(13) 0.0274(5) Uani 1 1 d . . . H38 H 0.3582 0.7689 0.5322 0.033 Uiso 1 1 calc R . . C39 C 0.76818(19) 0.53174(15) -0.03784(13) 0.0265(5) Uani 1 1 d . . . H39 H 0.7392 0.5278 -0.0929 0.032 Uiso 1 1 calc R . . C40 C 0.8524(2) 0.54347(14) 0.12333(13) 0.0258(5) Uani 1 1 d . . . H40 H 0.8812 0.5468 0.1784 0.031 Uiso 1 1 calc R . . C41 C 0.94906(19) 0.60497(15) 0.38049(13) 0.0269(5) Uani 1 1 d . . . H41 H 0.9511 0.5701 0.4236 0.032 Uiso 1 1 calc R . . C42 C 1.04778(19) 0.63945(16) 0.37368(14) 0.0302(5) Uani 1 1 d . . . H42 H 1.1180 0.6284 0.4121 0.036 Uiso 1 1 calc R . . C43 C 0.84564(17) 0.62139(14) 0.32382(12) 0.0214(4) Uani 1 1 d . . . H43 H 0.7776 0.5973 0.3285 0.026 Uiso 1 1 calc R . . C44 C 0.93142(18) 0.94638(15) 0.36383(15) 0.0301(5) Uani 1 1 d . . . H44 H 0.9922 0.9840 0.3857 0.036 Uiso 1 1 calc R . . C45 C 0.89872(19) 0.88958(15) 0.41075(14) 0.0284(5) Uani 1 1 d . . . H45 H 0.9384 0.8872 0.4648 0.034 Uiso 1 1 calc R . . C46 C 1.04466(19) 0.69026(16) 0.31079(15) 0.0329(6) Uani 1 1 d . . . H46 H 1.1130 0.7137 0.3060 0.039 Uiso 1 1 calc R . . C47 C 0.17056(18) 0.87998(14) 0.25260(13) 0.0242(5) Uani 1 1 d . . . H47 H 0.1051 0.8544 0.2599 0.029 Uiso 1 1 calc R . . C48 C 0.9038(2) 0.49146(16) 0.08329(14) 0.0313(5) Uani 1 1 d . . . H48 H 0.9687 0.4600 0.1108 0.038 Uiso 1 1 calc R . . C49 C 0.94219(18) 0.70721(15) 0.25460(13) 0.0257(5) Uani 1 1 d . . . H49 H 0.9406 0.7425 0.2118 0.031 Uiso 1 1 calc R . . C50 C 0.64122(16) 0.78584(12) 0.26881(11) 0.0156(4) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl3 0.0190(3) 0.0325(3) 0.0318(3) -0.0040(2) 0.0088(2) -0.0052(2) Cl2 0.0246(3) 0.0237(3) 0.0308(3) 0.0049(2) 0.0043(2) -0.0007(2) Cl4 0.0340(3) 0.0319(3) 0.0243(3) 0.0048(2) 0.0124(2) -0.0027(2) Cl1 0.0281(3) 0.0292(3) 0.0294(3) 0.0084(2) 0.0082(2) 0.0116(2) N4 0.0155(8) 0.0174(9) 0.0168(8) 0.0005(7) 0.0045(7) -0.0006(7) N3 0.0135(8) 0.0158(8) 0.0161(8) -0.0021(6) 0.0030(6) 0.0008(6) N2 0.0169(8) 0.0221(9) 0.0185(9) 0.0003(7) 0.0043(7) 0.0016(7) C8 0.0174(10) 0.0249(11) 0.0191(10) -0.0053(8) 0.0049(8) -0.0008(8) N1 0.0132(8) 0.0172(9) 0.0170(8) 0.0005(6) 0.0041(6) 0.0024(6) C10 0.0167(9) 0.0184(10) 0.0157(9) -0.0034(8) 0.0051(8) 0.0017(8) C11 0.0162(9) 0.0182(10) 0.0176(10) 0.0007(8) 0.0057(8) 0.0007(8) C12 0.0123(9) 0.0215(10) 0.0161(9) 0.0011(8) 0.0028(8) -0.0019(8) C13 0.0166(9) 0.0217(11) 0.0206(10) 0.0001(8) 0.0048(8) -0.0012(8) C14 0.0228(10) 0.0220(11) 0.0156(10) 0.0000(8) 0.0036(8) 0.0064(9) C15 0.0154(9) 0.0286(12) 0.0174(10) -0.0051(8) 0.0006(8) 0.0036(8) C16 0.0145(9) 0.0157(9) 0.0165(9) -0.0030(7) 0.0040(8) -0.0016(7) C17 0.0181(10) 0.0234(11) 0.0214(10) 0.0007(9) 0.0052(8) 0.0003(8) C18 0.0134(9) 0.0175(10) 0.0188(10) -0.0010(8) 0.0046(8) 0.0037(7) C19 0.0140(9) 0.0160(10) 0.0191(10) 0.0019(8) 0.0074(8) 0.0019(7) C20 0.0169(9) 0.0147(9) 0.0147(9) -0.0052(7) 0.0028(8) -0.0027(8) C21 0.0163(10) 0.0217(11) 0.0161(9) -0.0037(8) 0.0025(8) 0.0019(8) C22 0.0129(9) 0.0175(10) 0.0216(10) -0.0006(8) 0.0058(8) 0.0014(8) C23 0.0187(10) 0.0225(11) 0.0267(11) -0.0016(9) 0.0075(9) -0.0009(8) C24 0.0182(10) 0.0228(11) 0.0220(10) 0.0020(8) 0.0083(8) 0.0022(8) C25 0.0178(10) 0.0253(11) 0.0218(11) 0.0004(9) 0.0042(8) 0.0003(9) C26 0.0166(9) 0.0180(10) 0.0223(10) 0.0015(8) 0.0080(8) 0.0009(8) C27 0.0205(10) 0.0162(10) 0.0209(10) 0.0000(8) 0.0085(8) 0.0001(8) C28 0.0190(10) 0.0194(10) 0.0157(9) -0.0025(8) 0.0018(8) 0.0010(8) C29 0.0236(11) 0.0256(12) 0.0267(12) 0.0060(9) 0.0054(9) -0.0079(9) C30 0.0185(10) 0.0251(11) 0.0170(10) -0.0004(8) 0.0052(8) 0.0035(8) C31 0.0182(10) 0.0318(13) 0.0293(12) -0.0017(10) 0.0024(9) 0.0115(9) C32 0.0189(10) 0.0349(13) 0.0288(12) 0.0090(10) 0.0096(9) -0.0035(9) C33 0.0192(10) 0.0237(11) 0.0229(11) 0.0020(9) 0.0078(9) 0.0032(8) C34 0.0206(11) 0.0217(11) 0.0383(13) 0.0044(9) 0.0111(10) -0.0012(9) C35 0.0263(11) 0.0194(11) 0.0338(13) 0.0027(9) 0.0055(10) 0.0053(9) C36 0.0333(12) 0.0266(12) 0.0312(12) -0.0076(10) 0.0158(10) 0.0034(10) C37 0.0190(10) 0.0277(12) 0.0239(11) -0.0047(9) 0.0031(9) 0.0012(9) C38 0.0246(11) 0.0372(13) 0.0232(11) 0.0017(10) 0.0111(9) 0.0036(10) C39 0.0258(11) 0.0303(12) 0.0232(11) -0.0079(9) 0.0071(9) -0.0024(9) C40 0.0308(12) 0.0257(12) 0.0213(11) 0.0018(9) 0.0085(9) 0.0090(9) C41 0.0242(11) 0.0318(13) 0.0222(11) 0.0067(9) 0.0033(9) 0.0038(9) C42 0.0187(10) 0.0363(14) 0.0309(12) 0.0036(10) 0.0003(9) 0.0038(10) C43 0.0166(10) 0.0243(11) 0.0240(11) 0.0014(9) 0.0071(8) 0.0000(8) C44 0.0172(11) 0.0250(12) 0.0448(15) -0.0001(10) 0.0044(10) -0.0049(9) C45 0.0213(11) 0.0322(13) 0.0261(12) -0.0022(10) -0.0015(9) -0.0018(9) C46 0.0149(10) 0.0362(14) 0.0457(15) 0.0096(11) 0.0065(10) -0.0024(9) C47 0.0173(10) 0.0287(12) 0.0271(11) -0.0030(9) 0.0074(9) 0.0006(9) C48 0.0347(13) 0.0329(13) 0.0275(12) 0.0049(10) 0.0111(10) 0.0143(11) C49 0.0192(10) 0.0284(12) 0.0299(12) 0.0083(10) 0.0080(9) 0.0010(9) C50 0.0145(9) 0.0171(10) 0.0159(9) 0.0007(8) 0.0055(8) 0.0014(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 Cl3 C8 1.736(2) . ? Cl2 C28 1.727(2) . ? Cl4 C24 1.753(2) . ? Cl1 C14 1.736(2) . ? N4 C16 1.286(2) . ? N4 C50 1.476(2) . ? N3 C20 1.284(2) . ? N3 C50 1.470(2) . ? N2 C11 1.305(3) . ? N2 C26 1.386(3) . ? C8 C15 1.376(3) . ? C8 C28 1.399(3) . ? N1 C11 1.381(2) . ? N1 C19 1.396(2) . ? N1 C50 1.475(2) . ? C10 C17 1.396(3) . ? C10 C23 1.406(3) . ? C10 C20 1.474(3) . ? C11 C21 1.489(3) . ? C12 C33 1.386(3) . ? C12 C13 1.397(3) . ? C12 C16 1.480(3) . ? C13 C29 1.390(3) . ? C13 H13 0.9500 . ? C14 C30 1.391(3) . ? C14 C15 1.392(3) . ? C15 H15 0.9500 . ? C16 C20 1.512(3) . ? C17 C47 1.393(3) . ? C17 H17 0.9500 . ? C18 C43 1.389(3) . ? C18 C49 1.389(3) . ? C18 C19 1.485(3) . ? C19 C26 1.380(3) . ? C21 C30 1.380(3) . ? C21 C28 1.393(3) . ? C22 C25 1.395(3) . ? C22 C24 1.397(3) . ? C22 C50 1.523(3) . ? C23 C35 1.382(3) . ? C23 H23 0.9500 . ? C24 C34 1.388(3) . ? C25 C45 1.389(3) . ? C25 H25 0.9500 . ? C26 C27 1.474(3) . ? C27 C40 1.395(3) . ? C27 C37 1.400(3) . ? C29 C32 1.386(3) . ? C29 H29 0.9500 . ? C30 H30 0.9500 . ? C31 C47 1.367(3) . ? C31 C35 1.401(3) . ? C31 H31 0.9500 . ? C32 C38 1.386(3) . ? C32 H32 0.9500 . ? C33 C38 1.396(3) . ? C33 H33 0.9500 . ? C34 C44 1.385(3) . ? C34 H34 0.9500 . ? C35 H35 0.9500 . ? C36 C39 1.387(3) . ? C36 C48 1.398(3) . ? C36 H36 0.9500 . ? C37 C39 1.389(3) . ? C37 H37 0.9500 . ? C38 H38 0.9500 . ? C39 H39 0.9500 . ? C40 C48 1.374(3) . ? C40 H40 0.9500 . ? C41 C42 1.376(3) . ? C41 C43 1.401(3) . ? C41 H41 0.9500 . ? C42 C46 1.384(3) . ? C42 H42 0.9500 . ? C43 H43 0.9500 . ? C44 C45 1.380(3) . ? C44 H44 0.9500 . ? C45 H45 0.9500 . ? C46 C49 1.390(3) . ? C46 H46 0.9500 . ? C47 H47 0.9500 . ? C48 H48 0.9500 . ? C49 H49 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 C16 N4 C50 105.94(16) . . ? C20 N3 C50 106.19(16) . . ? C11 N2 C26 106.57(17) . . ? C15 C8 C28 120.7(2) . . ? C15 C8 Cl3 118.95(16) . . ? C28 C8 Cl3 120.32(17) . . ? C11 N1 C19 106.44(16) . . ? C11 N1 C50 127.52(16) . . ? C19 N1 C50 125.90(16) . . ? C17 C10 C23 119.37(19) . . ? C17 C10 C20 121.63(18) . . ? C23 C10 C20 118.61(18) . . ? N2 C11 N1 111.69(17) . . ? N2 C11 C21 120.84(18) . . ? N1 C11 C21 127.31(17) . . ? C33 C12 C13 119.93(19) . . ? C33 C12 C16 121.87(19) . . ? C13 C12 C16 118.19(18) . . ? C29 C13 C12 119.8(2) . . ? C29 C13 H13 120.1 . . ? C12 C13 H13 120.1 . . ? C30 C14 C15 121.9(2) . . ? C30 C14 Cl1 119.29(17) . . ? C15 C14 Cl1 118.75(16) . . ? C8 C15 C14 118.14(19) . . ? C8 C15 H15 120.9 . . ? C14 C15 H15 120.9 . . ? N4 C16 C12 122.14(18) . . ? N4 C16 C20 109.84(17) . . ? C12 C16 C20 128.00(17) . . ? C47 C17 C10 120.4(2) . . ? C47 C17 H17 119.8 . . ? C10 C17 H17 119.8 . . ? C43 C18 C49 119.27(19) . . ? C43 C18 C19 120.10(18) . . ? C49 C18 C19 120.36(18) . . ? C26 C19 N1 105.56(16) . . ? C26 C19 C18 129.79(18) . . ? N1 C19 C18 124.61(17) . . ? N3 C20 C10 120.00(18) . . ? N3 C20 C16 109.90(17) . . ? C10 C20 C16 129.86(17) . . ? C30 C21 C28 119.30(19) . . ? C30 C21 C11 120.68(19) . . ? C28 C21 C11 119.90(19) . . ? C25 C22 C24 117.55(19) . . ? C25 C22 C50 120.16(18) . . ? C24 C22 C50 122.00(18) . . ? C35 C23 C10 119.7(2) . . ? C35 C23 H23 120.2 . . ? C10 C23 H23 120.2 . . ? C34 C24 C22 121.7(2) . . ? C34 C24 Cl4 116.51(17) . . ? C22 C24 Cl4 121.82(16) . . ? C45 C25 C22 120.9(2) . . ? C45 C25 H25 119.5 . . ? C22 C25 H25 119.5 . . ? C19 C26 N2 109.74(17) . . ? C19 C26 C27 131.26(19) . . ? N2 C26 C27 118.99(18) . . ? C40 C27 C37 118.25(19) . . ? C40 C27 C26 123.39(19) . . ? C37 C27 C26 118.36(19) . . ? C21 C28 C8 120.43(19) . . ? C21 C28 Cl2 119.82(16) . . ? C8 C28 Cl2 119.73(16) . . ? C32 C29 C13 120.1(2) . . ? C32 C29 H29 119.9 . . ? C13 C29 H29 119.9 . . ? C21 C30 C14 119.5(2) . . ? C21 C30 H30 120.3 . . ? C14 C30 H30 120.3 . . ? C47 C31 C35 120.7(2) . . ? C47 C31 H31 119.7 . . ? C35 C31 H31 119.7 . . ? C29 C32 C38 120.3(2) . . ? C29 C32 H32 119.9 . . ? C38 C32 H32 119.9 . . ? C12 C33 C38 120.0(2) . . ? C12 C33 H33 120.0 . . ? C38 C33 H33 120.0 . . ? C44 C34 C24 119.7(2) . . ? C44 C34 H34 120.2 . . ? C24 C34 H34 120.2 . . ? C23 C35 C31 120.1(2) . . ? C23 C35 H35 120.0 . . ? C31 C35 H35 120.0 . . ? C39 C36 C48 119.6(2) . . ? C39 C36 H36 120.2 . . ? C48 C36 H36 120.2 . . ? C39 C37 C27 121.2(2) . . ? C39 C37 H37 119.4 . . ? C27 C37 H37 119.4 . . ? C32 C38 C33 119.9(2) . . ? C32 C38 H38 120.1 . . ? C33 C38 H38 120.1 . . ? C36 C39 C37 119.6(2) . . ? C36 C39 H39 120.2 . . ? C37 C39 H39 120.2 . . ? C48 C40 C27 120.9(2) . . ? C48 C40 H40 119.6 . . ? C27 C40 H40 119.6 . . ? C42 C41 C43 120.0(2) . . ? C42 C41 H41 120.0 . . ? C43 C41 H41 120.0 . . ? C41 C42 C46 119.9(2) . . ? C41 C42 H42 120.0 . . ? C46 C42 H42 120.0 . . ? C18 C43 C41 120.3(2) . . ? C18 C43 H43 119.9 . . ? C41 C43 H43 119.9 . . ? C45 C44 C34 119.7(2) . . ? C45 C44 H44 120.1 . . ? C34 C44 H44 120.1 . . ? C44 C45 C25 120.5(2) . . ? C44 C45 H45 119.8 . . ? C25 C45 H45 119.8 . . ? C42 C46 C49 120.4(2) . . ? C42 C46 H46 119.8 . . ? C49 C46 H46 119.8 . . ? C31 C47 C17 119.8(2) . . ? C31 C47 H47 120.1 . . ? C17 C47 H47 120.1 . . ? C40 C48 C36 120.5(2) . . ? C40 C48 H48 119.7 . . ? C36 C48 H48 119.7 . . ? C18 C49 C46 120.2(2) . . ? C18 C49 H49 119.9 . . ? C46 C49 H49 119.9 . . ? N3 C50 N1 108.09(15) . . ? N3 C50 N4 108.08(15) . . ? N1 C50 N4 108.50(16) . . ? N3 C50 C22 106.95(16) . . ? N1 C50 C22 113.67(15) . . ? N4 C50 C22 111.35(16) . . ? _diffrn_measured_fraction_theta_max 0.978 _diffrn_reflns_theta_full 27.56 _diffrn_measured_fraction_theta_full 0.978 _refine_diff_density_max 0.999 _refine_diff_density_min -0.566 _refine_diff_density_rms 0.068 # Attachment '2_2.cif' data_sad _database_code_depnum_ccdc_archive 'CCDC 722515' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C54 H36 Cl6 N4' _chemical_formula_weight 953.57 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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 17.8938(4) _cell_length_b 14.1917(3) _cell_length_c 18.1886(3) _cell_angle_alpha 90.00 _cell_angle_beta 97.6160(10) _cell_angle_gamma 90.00 _cell_volume 4578.13(16) _cell_formula_units_Z 4 _cell_measurement_temperature 103 _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 0.16 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.383 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1960 _exptl_absorpt_coefficient_mu 0.418 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9210 _exptl_absorpt_correction_T_max 0.9361 _exptl_absorpt_process_details ' SADABS Sheldrick 1996 ' _exptl_special_details ; ? ; _diffrn_ambient_temperature 103 _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 81831 _diffrn_reflns_av_R_equivalents 0.0531 _diffrn_reflns_av_sigmaI/netI 0.0480 _diffrn_reflns_limit_h_min -26 _diffrn_reflns_limit_h_max 27 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 1.50 _diffrn_reflns_theta_max 33.00 _reflns_number_total 16461 _reflns_number_gt 11493 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0528P)^2^+1.3271P] 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 ' no refined H ' _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 16461 _refine_ls_number_parameters 577 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0752 _refine_ls_R_factor_gt 0.0435 _refine_ls_wR_factor_ref 0.1107 _refine_ls_wR_factor_gt 0.1007 _refine_ls_goodness_of_fit_ref 1.025 _refine_ls_restrained_S_all 1.025 _refine_ls_shift/su_max 0.011 _refine_ls_shift/su_mean 0.001 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 Cl1 Cl 0.291748(19) 0.11350(2) 0.182765(19) 0.01942(7) Uani 1 1 d . . . Cl2 Cl 0.14158(2) 0.16324(3) 0.24463(2) 0.02926(9) Uani 1 1 d . . . Cl3 Cl 0.28693(2) 0.43403(3) 0.41627(2) 0.02617(8) Uani 1 1 d . . . Cl4 Cl 0.51625(2) 0.44113(3) 0.24060(2) 0.02880(9) Uani 1 1 d . . . Cl5 Cl 0.63445(3) 0.57325(3) 0.18089(4) 0.05169(16) Uani 1 1 d . . . Cl6 Cl 0.59379(3) 0.39360(4) -0.08260(3) 0.04194(13) Uani 1 1 d . . . N1 N 0.47207(6) 0.16346(8) 0.30088(6) 0.0134(2) Uani 1 1 d . . . N2 N 0.46649(6) 0.23721(8) 0.19173(6) 0.0121(2) Uani 1 1 d . . . N3 N 0.37502(6) 0.35372(8) 0.14549(6) 0.0134(2) Uani 1 1 d . . . N4 N 0.40768(6) 0.23091(8) 0.06569(6) 0.0131(2) Uani 1 1 d . . . C1 C 0.43120(7) 0.21904(9) 0.25344(7) 0.0127(2) Uani 1 1 d . . . C2 C 0.53668(7) 0.14251(9) 0.26956(7) 0.0122(2) Uani 1 1 d . . . C3 C 0.53518(7) 0.18780(9) 0.20214(7) 0.0123(2) Uani 1 1 d . . . C4 C 0.43730(7) 0.29495(9) 0.12674(7) 0.0127(2) Uani 1 1 d . . . C5 C 0.31650(7) 0.32999(9) 0.09986(7) 0.0124(2) Uani 1 1 d . . . C6 C 0.33719(7) 0.25169(9) 0.04941(7) 0.0124(2) Uani 1 1 d . . . C11 C 0.35668(7) 0.25304(9) 0.27077(7) 0.0134(2) Uani 1 1 d . . . C12 C 0.29032(7) 0.20388(10) 0.24583(7) 0.0153(2) Uani 1 1 d . . . C13 C 0.22312(8) 0.22621(11) 0.27333(8) 0.0191(3) Uani 1 1 d . . . C14 C 0.22124(8) 0.29779(11) 0.32539(8) 0.0222(3) Uani 1 1 d . . . H14A H 0.1757 0.3130 0.3443 0.027 Uiso 1 1 calc R . . C15 C 0.28711(9) 0.34634(10) 0.34907(8) 0.0193(3) Uani 1 1 d . . . C16 C 0.35463(8) 0.32526(10) 0.32260(8) 0.0166(3) Uani 1 1 d . . . H16A H 0.3990 0.3598 0.3397 0.020 Uiso 1 1 calc R . . C21 C 0.59267(7) 0.07663(9) 0.30821(7) 0.0130(2) Uani 1 1 d . . . C22 C 0.59683(8) 0.06707(10) 0.38543(8) 0.0158(2) Uani 1 1 d . . . H22A H 0.5648 0.1038 0.4118 0.019 Uiso 1 1 calc R . . C23 C 0.64769(8) 0.00400(10) 0.42376(8) 0.0199(3) Uani 1 1 d . . . H23A H 0.6501 -0.0020 0.4760 0.024 Uiso 1 1 calc R . . C24 C 0.69484(8) -0.05011(10) 0.38574(9) 0.0209(3) Uani 1 1 d . . . H24A H 0.7299 -0.0925 0.4120 0.025 Uiso 1 1 calc R . . C25 C 0.69036(8) -0.04178(10) 0.30897(9) 0.0217(3) Uani 1 1 d . . . H25A H 0.7221 -0.0792 0.2828 0.026 Uiso 1 1 calc R . . C26 C 0.63972(8) 0.02096(10) 0.27027(8) 0.0170(3) Uani 1 1 d . . . H26A H 0.6371 0.0260 0.2179 0.020 Uiso 1 1 calc R . . C31 C 0.59402(7) 0.19101(9) 0.15174(7) 0.0129(2) Uani 1 1 d . . . C32 C 0.66592(8) 0.22450(10) 0.18001(8) 0.0176(3) Uani 1 1 d . . . H32A H 0.6753 0.2464 0.2297 0.021 Uiso 1 1 calc R . . C33 C 0.72372(8) 0.22579(11) 0.13556(9) 0.0216(3) Uani 1 1 d . . . H33A H 0.7725 0.2474 0.1555 0.026 Uiso 1 1 calc R . . C34 C 0.71044(8) 0.19563(10) 0.06230(9) 0.0204(3) Uani 1 1 d . . . H34A H 0.7496 0.1981 0.0318 0.024 Uiso 1 1 calc R . . C35 C 0.63940(8) 0.16181(10) 0.03384(8) 0.0186(3) Uani 1 1 d . . . H35A H 0.6302 0.1408 -0.0161 0.022 Uiso 1 1 calc R . . C36 C 0.58177(8) 0.15862(10) 0.07845(8) 0.0157(2) Uani 1 1 d . . . H36A H 0.5338 0.1342 0.0589 0.019 Uiso 1 1 calc R . . C41 C 0.49809(7) 0.36018(10) 0.10238(8) 0.0173(3) Uani 1 1 d . . . C42 C 0.53490(8) 0.42828(10) 0.15034(10) 0.0228(3) Uani 1 1 d . . . C43 C 0.58887(9) 0.48698(11) 0.12403(12) 0.0319(4) Uani 1 1 d . . . C44 C 0.60720(9) 0.47791(12) 0.05295(12) 0.0351(4) Uani 1 1 d . . . H44A H 0.6442 0.5176 0.0361 0.042 Uiso 1 1 calc R . . C45 C 0.57077(9) 0.41008(12) 0.00658(10) 0.0290(4) Uani 1 1 d . . . C46 C 0.51595(8) 0.35241(11) 0.03039(9) 0.0212(3) Uani 1 1 d . . . H46A H 0.4905 0.3074 -0.0026 0.025 Uiso 1 1 calc R . . C51 C 0.24219(7) 0.37352(9) 0.10363(7) 0.0128(2) Uani 1 1 d . . . C52 C 0.17555(8) 0.32087(10) 0.08950(7) 0.0158(2) Uani 1 1 d . . . H52A H 0.1775 0.2568 0.0747 0.019 Uiso 1 1 calc R . . C53 C 0.10658(8) 0.36239(11) 0.09722(8) 0.0205(3) Uani 1 1 d . . . H53A H 0.0616 0.3263 0.0884 0.025 Uiso 1 1 calc R . . C54 C 0.10326(8) 0.45667(11) 0.11777(8) 0.0218(3) Uani 1 1 d . . . H54A H 0.0560 0.4851 0.1221 0.026 Uiso 1 1 calc R . . C55 C 0.16923(8) 0.50926(11) 0.13193(8) 0.0201(3) Uani 1 1 d . . . H55A H 0.1668 0.5737 0.1457 0.024 Uiso 1 1 calc R . . C56 C 0.23875(8) 0.46807(10) 0.12606(8) 0.0164(3) Uani 1 1 d . . . H56A H 0.2838 0.5037 0.1372 0.020 Uiso 1 1 calc R . . C61 C 0.28799(7) 0.20287(9) -0.01045(7) 0.0132(2) Uani 1 1 d . . . C62 C 0.29650(8) 0.10579(10) -0.02064(8) 0.0174(3) Uani 1 1 d . . . H62A H 0.3326 0.0714 0.0118 0.021 Uiso 1 1 calc R . . C63 C 0.25209(9) 0.05956(11) -0.07823(9) 0.0229(3) Uani 1 1 d . . . H63A H 0.2583 -0.0062 -0.0853 0.028 Uiso 1 1 calc R . . C64 C 0.19858(9) 0.10959(11) -0.12556(8) 0.0228(3) Uani 1 1 d . . . H64A H 0.1681 0.0779 -0.1647 0.027 Uiso 1 1 calc R . . C65 C 0.18981(8) 0.20566(11) -0.11551(8) 0.0205(3) Uani 1 1 d . . . H65A H 0.1531 0.2394 -0.1477 0.025 Uiso 1 1 calc R . . C66 C 0.23436(8) 0.25292(10) -0.05870(7) 0.0165(3) Uani 1 1 d . . . H66A H 0.2285 0.3189 -0.0526 0.020 Uiso 1 1 calc R . . C11S C -0.02630(10) 0.41577(13) 0.40061(10) 0.0318(4) Uani 1 1 d . . . H11A H -0.0403 0.4378 0.4462 0.038 Uiso 1 1 calc R . . C12S C -0.05911(11) 0.33509(13) 0.36782(11) 0.0365(4) Uani 1 1 d . . . H12A H -0.0955 0.3014 0.3910 0.044 Uiso 1 1 calc R . . C13S C -0.03884(12) 0.30357(13) 0.30122(12) 0.0396(5) Uani 1 1 d . . . H13A H -0.0611 0.2479 0.2790 0.047 Uiso 1 1 calc R . . C14S C 0.01365(11) 0.35271(12) 0.26667(11) 0.0329(4) Uani 1 1 d . . . H14B H 0.0268 0.3312 0.2206 0.040 Uiso 1 1 calc R . . C15S C 0.04703(9) 0.43334(12) 0.29942(10) 0.0269(3) Uani 1 1 d . . . H15A H 0.0832 0.4670 0.2759 0.032 Uiso 1 1 calc R . . C16S C 0.02745(9) 0.46463(12) 0.36645(9) 0.0282(3) Uani 1 1 d . . . H16B H 0.0506 0.5194 0.3892 0.034 Uiso 1 1 calc R . . C21S C -0.07728(11) 0.22703(18) 0.05951(14) 0.0499(6) Uani 1 1 d . . . H21A H -0.1169 0.2633 0.0752 0.060 Uiso 1 1 calc R . . C22S C -0.04432(15) 0.15420(17) 0.10382(12) 0.0516(6) Uani 1 1 d . . . H22B H -0.0616 0.1401 0.1498 0.062 Uiso 1 1 calc R . . C23S C 0.01351(15) 0.10274(15) 0.08057(12) 0.0476(5) Uani 1 1 d . . . H23B H 0.0361 0.0530 0.1106 0.057 Uiso 1 1 calc R . . C24S C 0.03869(12) 0.12289(14) 0.01428(11) 0.0385(4) Uani 1 1 d . . . H24B H 0.0787 0.0872 -0.0012 0.046 Uiso 1 1 calc R . . C25S C 0.00637(11) 0.19438(14) -0.02989(10) 0.0345(4) Uani 1 1 d . . . H25B H 0.0242 0.2079 -0.0757 0.041 Uiso 1 1 calc R . . C26S C -0.05162(10) 0.24642(15) -0.00819(12) 0.0398(5) Uani 1 1 d . . . H26B H -0.0742 0.2954 -0.0391 0.048 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 Cl1 0.02014(15) 0.02045(16) 0.01803(15) -0.00259(12) 0.00380(12) -0.00274(13) Cl2 0.01403(15) 0.0422(2) 0.0320(2) -0.00045(17) 0.00474(14) -0.00507(15) Cl3 0.0377(2) 0.02101(17) 0.02199(17) -0.00178(13) 0.01204(15) 0.00862(15) Cl4 0.02177(17) 0.02538(19) 0.0373(2) -0.01062(16) -0.00326(15) -0.00228(14) Cl5 0.0235(2) 0.0212(2) 0.1115(5) -0.0177(2) 0.0131(3) -0.00781(16) Cl6 0.0351(2) 0.0460(3) 0.0510(3) 0.0297(2) 0.0288(2) 0.0133(2) N1 0.0118(5) 0.0135(5) 0.0151(5) -0.0003(4) 0.0024(4) 0.0011(4) N2 0.0106(5) 0.0134(5) 0.0124(5) 0.0010(4) 0.0018(4) 0.0008(4) N3 0.0118(5) 0.0128(5) 0.0157(5) 0.0020(4) 0.0023(4) 0.0014(4) N4 0.0135(5) 0.0144(5) 0.0118(5) 0.0022(4) 0.0035(4) 0.0014(4) C1 0.0114(5) 0.0131(6) 0.0137(6) -0.0012(4) 0.0025(4) -0.0001(4) C2 0.0112(5) 0.0117(5) 0.0136(6) -0.0017(4) 0.0011(4) -0.0001(4) C3 0.0096(5) 0.0125(6) 0.0149(6) -0.0008(4) 0.0018(4) 0.0009(4) C4 0.0108(5) 0.0132(6) 0.0142(6) 0.0016(5) 0.0019(4) 0.0014(4) C5 0.0131(5) 0.0117(5) 0.0126(5) 0.0022(4) 0.0026(4) 0.0008(4) C6 0.0137(5) 0.0118(5) 0.0122(5) 0.0028(4) 0.0029(4) 0.0014(4) C11 0.0126(5) 0.0143(6) 0.0137(6) 0.0018(5) 0.0033(4) 0.0028(5) C12 0.0139(6) 0.0178(6) 0.0147(6) 0.0017(5) 0.0032(5) 0.0014(5) C13 0.0116(6) 0.0272(7) 0.0188(6) 0.0052(5) 0.0029(5) 0.0006(5) C14 0.0180(7) 0.0287(8) 0.0213(7) 0.0043(6) 0.0074(5) 0.0086(6) C15 0.0246(7) 0.0185(6) 0.0162(6) 0.0014(5) 0.0075(5) 0.0068(5) C16 0.0169(6) 0.0172(6) 0.0163(6) 0.0007(5) 0.0040(5) 0.0031(5) C21 0.0111(5) 0.0108(5) 0.0168(6) 0.0009(4) 0.0005(4) -0.0014(4) C22 0.0158(6) 0.0148(6) 0.0164(6) 0.0002(5) 0.0004(5) -0.0003(5) C23 0.0216(7) 0.0178(6) 0.0187(6) 0.0026(5) -0.0035(5) -0.0009(5) C24 0.0176(6) 0.0163(6) 0.0270(7) 0.0038(5) -0.0036(5) 0.0027(5) C25 0.0183(6) 0.0183(7) 0.0291(8) 0.0025(6) 0.0049(6) 0.0057(5) C26 0.0173(6) 0.0151(6) 0.0188(6) 0.0014(5) 0.0032(5) 0.0021(5) C31 0.0120(5) 0.0111(5) 0.0158(6) 0.0016(4) 0.0031(5) 0.0017(4) C32 0.0143(6) 0.0175(6) 0.0216(7) -0.0033(5) 0.0043(5) -0.0020(5) C33 0.0156(6) 0.0203(7) 0.0300(8) -0.0031(6) 0.0078(6) -0.0046(5) C34 0.0191(7) 0.0170(6) 0.0276(7) -0.0012(5) 0.0130(6) -0.0007(5) C35 0.0209(7) 0.0180(6) 0.0181(6) 0.0006(5) 0.0069(5) 0.0029(5) C36 0.0141(6) 0.0161(6) 0.0172(6) 0.0006(5) 0.0034(5) 0.0008(5) C41 0.0106(5) 0.0132(6) 0.0284(7) 0.0063(5) 0.0037(5) 0.0016(5) C42 0.0134(6) 0.0144(6) 0.0401(9) 0.0015(6) 0.0018(6) 0.0028(5) C43 0.0155(7) 0.0122(7) 0.0681(13) 0.0022(7) 0.0057(7) 0.0005(5) C44 0.0177(7) 0.0195(7) 0.0711(13) 0.0188(8) 0.0173(8) 0.0033(6) C45 0.0204(7) 0.0237(8) 0.0460(10) 0.0196(7) 0.0159(7) 0.0085(6) C46 0.0160(6) 0.0201(7) 0.0288(7) 0.0114(6) 0.0081(6) 0.0056(5) C51 0.0117(5) 0.0151(6) 0.0116(5) 0.0003(4) 0.0018(4) 0.0022(4) C52 0.0150(6) 0.0167(6) 0.0160(6) -0.0023(5) 0.0032(5) -0.0006(5) C53 0.0121(6) 0.0286(8) 0.0209(7) -0.0043(6) 0.0026(5) -0.0010(5) C54 0.0150(6) 0.0319(8) 0.0186(7) -0.0046(6) 0.0028(5) 0.0076(6) C55 0.0223(7) 0.0195(7) 0.0181(6) -0.0056(5) 0.0015(5) 0.0070(5) C56 0.0153(6) 0.0165(6) 0.0166(6) -0.0023(5) -0.0003(5) 0.0008(5) C61 0.0133(6) 0.0150(6) 0.0115(5) 0.0009(4) 0.0025(4) 0.0017(5) C62 0.0188(6) 0.0155(6) 0.0175(6) 0.0015(5) 0.0005(5) 0.0034(5) C63 0.0270(7) 0.0166(7) 0.0241(7) -0.0029(5) -0.0007(6) 0.0018(6) C64 0.0228(7) 0.0256(7) 0.0186(7) -0.0052(6) -0.0032(5) 0.0006(6) C65 0.0207(7) 0.0254(7) 0.0143(6) 0.0002(5) -0.0011(5) 0.0071(6) C66 0.0182(6) 0.0161(6) 0.0153(6) 0.0012(5) 0.0028(5) 0.0048(5) C11S 0.0359(9) 0.0378(10) 0.0228(8) 0.0062(7) 0.0075(7) 0.0122(8) C12S 0.0446(11) 0.0294(9) 0.0406(10) 0.0098(8) 0.0241(9) 0.0026(8) C13S 0.0534(12) 0.0210(8) 0.0500(11) -0.0018(8) 0.0282(10) -0.0040(8) C14S 0.0422(10) 0.0242(8) 0.0369(9) 0.0000(7) 0.0222(8) 0.0039(7) C15S 0.0246(7) 0.0253(8) 0.0322(8) 0.0066(6) 0.0080(6) 0.0048(6) C16S 0.0257(8) 0.0304(8) 0.0271(8) 0.0028(7) -0.0013(6) 0.0066(7) C21S 0.0226(9) 0.0583(14) 0.0700(15) -0.0295(12) 0.0111(9) -0.0151(9) C22S 0.0681(15) 0.0543(14) 0.0356(11) -0.0116(10) 0.0183(10) -0.0346(12) C23S 0.0727(16) 0.0294(10) 0.0373(11) -0.0001(8) -0.0048(10) -0.0102(10) C24S 0.0423(11) 0.0335(10) 0.0384(10) -0.0112(8) 0.0002(8) -0.0034(8) C25S 0.0359(9) 0.0400(10) 0.0264(8) -0.0047(7) -0.0001(7) -0.0134(8) C26S 0.0278(9) 0.0388(10) 0.0478(11) -0.0028(9) -0.0137(8) -0.0079(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 Cl1 C12 1.7233(14) . ? Cl2 C13 1.7315(15) . ? Cl3 C15 1.7445(15) . ? Cl4 C42 1.7278(18) . ? Cl5 C43 1.7350(19) . ? Cl6 C45 1.7414(19) . ? N1 C1 1.3169(17) . ? N1 C2 1.3871(16) . ? N2 C1 1.3832(16) . ? N2 C3 1.4059(16) . ? N2 C4 1.4757(16) . ? N3 C5 1.2917(17) . ? N3 C4 1.4679(16) . ? N4 C6 1.2910(16) . ? N4 C4 1.4777(17) . ? C1 C11 1.4905(17) . ? C2 C3 1.3816(18) . ? C2 C21 1.4784(18) . ? C3 C31 1.4855(18) . ? C4 C41 1.5375(18) . ? C5 C51 1.4760(17) . ? C5 C6 1.5179(18) . ? C6 C61 1.4786(18) . ? C11 C16 1.3964(19) . ? C11 C12 1.3998(18) . ? C12 C13 1.3985(18) . ? C13 C14 1.392(2) . ? C14 C15 1.384(2) . ? C15 C16 1.3910(19) . ? C21 C26 1.4011(19) . ? C21 C22 1.4033(18) . ? C22 C23 1.3953(19) . ? C23 C24 1.391(2) . ? C24 C25 1.393(2) . ? C25 C26 1.3928(19) . ? C31 C36 1.3996(19) . ? C31 C32 1.4036(18) . ? C32 C33 1.395(2) . ? C33 C34 1.390(2) . ? C34 C35 1.393(2) . ? C35 C36 1.3948(19) . ? C41 C46 1.393(2) . ? C41 C42 1.406(2) . ? C42 C43 1.406(2) . ? C43 C44 1.381(3) . ? C44 C45 1.384(3) . ? C45 C46 1.390(2) . ? C51 C52 1.4017(18) . ? C51 C56 1.4062(19) . ? C52 C53 1.3914(19) . ? C53 C54 1.393(2) . ? C54 C55 1.392(2) . ? C55 C56 1.3912(19) . ? C61 C62 1.4012(19) . ? C61 C66 1.4044(18) . ? C62 C63 1.392(2) . ? C63 C64 1.394(2) . ? C64 C65 1.387(2) . ? C65 C66 1.391(2) . ? C11S C12S 1.385(3) . ? C11S C16S 1.397(3) . ? C12S C13S 1.384(3) . ? C13S C14S 1.386(2) . ? C14S C15S 1.388(3) . ? C15S C16S 1.386(2) . ? C21S C22S 1.393(4) . ? C21S C26S 1.397(3) . ? C22S C23S 1.378(4) . ? C23S C24S 1.372(3) . ? C24S C25S 1.373(3) . ? C25S C26S 1.374(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 C1 N1 C2 106.26(11) . . ? C1 N2 C3 106.43(10) . . ? C1 N2 C4 127.04(10) . . ? C3 N2 C4 126.52(10) . . ? C5 N3 C4 106.16(11) . . ? C6 N4 C4 105.91(11) . . ? N1 C1 N2 111.69(11) . . ? N1 C1 C11 119.34(11) . . ? N2 C1 C11 128.96(11) . . ? C3 C2 N1 110.22(11) . . ? C3 C2 C21 130.42(12) . . ? N1 C2 C21 119.31(11) . . ? C2 C3 N2 105.38(11) . . ? C2 C3 C31 129.05(11) . . ? N2 C3 C31 125.46(11) . . ? N3 C4 N2 109.17(10) . . ? N3 C4 N4 108.44(10) . . ? N2 C4 N4 108.31(10) . . ? N3 C4 C41 108.22(10) . . ? N2 C4 C41 112.11(10) . . ? N4 C4 C41 110.54(11) . . ? N3 C5 C51 121.31(12) . . ? N3 C5 C6 109.72(11) . . ? C51 C5 C6 128.90(11) . . ? N4 C6 C61 122.02(12) . . ? N4 C6 C5 109.74(11) . . ? C61 C6 C5 128.25(11) . . ? C16 C11 C12 119.18(12) . . ? C16 C11 C1 118.99(12) . . ? C12 C11 C1 120.96(12) . . ? C13 C12 C11 120.25(13) . . ? C13 C12 Cl1 119.74(11) . . ? C11 C12 Cl1 119.99(10) . . ? C14 C13 C12 120.53(13) . . ? C14 C13 Cl2 119.10(11) . . ? C12 C13 Cl2 120.35(12) . . ? C15 C14 C13 118.60(13) . . ? C14 C15 C16 121.88(13) . . ? C14 C15 Cl3 119.51(11) . . ? C16 C15 Cl3 118.57(12) . . ? C15 C16 C11 119.55(13) . . ? C26 C21 C22 118.87(12) . . ? C26 C21 C2 122.42(12) . . ? C22 C21 C2 118.67(12) . . ? C23 C22 C21 120.45(13) . . ? C24 C23 C22 120.28(13) . . ? C23 C24 C25 119.56(13) . . ? C26 C25 C24 120.53(14) . . ? C25 C26 C21 120.31(13) . . ? C36 C31 C32 118.71(12) . . ? C36 C31 C3 122.91(12) . . ? C32 C31 C3 118.33(12) . . ? C33 C32 C31 120.41(13) . . ? C34 C33 C32 120.40(14) . . ? C33 C34 C35 119.61(13) . . ? C34 C35 C36 120.25(13) . . ? C35 C36 C31 120.58(13) . . ? C46 C41 C42 119.38(13) . . ? C46 C41 C4 118.85(13) . . ? C42 C41 C4 121.76(13) . . ? C41 C42 C43 118.85(16) . . ? C41 C42 Cl4 121.90(12) . . ? C43 C42 Cl4 119.25(13) . . ? C44 C43 C42 121.48(16) . . ? C44 C43 Cl5 118.20(13) . . ? C42 C43 Cl5 120.32(15) . . ? C43 C44 C45 118.94(15) . . ? C44 C45 C46 120.95(17) . . ? C44 C45 Cl6 120.69(12) . . ? C46 C45 Cl6 118.35(15) . . ? C45 C46 C41 120.38(16) . . ? C52 C51 C56 119.53(12) . . ? C52 C51 C5 121.20(12) . . ? C56 C51 C5 119.16(12) . . ? C53 C52 C51 120.01(13) . . ? C52 C53 C54 120.26(13) . . ? C55 C54 C53 119.97(13) . . ? C56 C55 C54 120.38(13) . . ? C55 C56 C51 119.81(13) . . ? C62 C61 C66 119.46(12) . . ? C62 C61 C6 119.58(12) . . ? C66 C61 C6 120.93(12) . . ? C63 C62 C61 120.11(13) . . ? C62 C63 C64 120.09(14) . . ? C65 C64 C63 119.98(14) . . ? C64 C65 C66 120.53(13) . . ? C65 C66 C61 119.82(13) . . ? C12S C11S C16S 119.77(16) . . ? C13S C12S C11S 119.91(17) . . ? C12S C13S C14S 120.42(18) . . ? C13S C14S C15S 119.96(17) . . ? C16S C15S C14S 119.82(16) . . ? C15S C16S C11S 120.11(17) . . ? C22S C21S C26S 119.5(2) . . ? C23S C22S C21S 119.6(2) . . ? C24S C23S C22S 120.4(2) . . ? C23S C24S C25S 120.4(2) . . ? C24S C25S C26S 120.30(19) . . ? C25S C26S C21S 119.8(2) . . ? _diffrn_measured_fraction_theta_max 0.953 _diffrn_reflns_theta_full 33.00 _diffrn_measured_fraction_theta_full 0.953 _refine_diff_density_max 1.169 _refine_diff_density_min -0.939 _refine_diff_density_rms 0.066