# Electronic Supplementary Material for CrystEngComm # This journal is (c) The Royal Society of Chemistry 2008 data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Leroy Cronin' _publ_contact_author_email LEE@CHEM.GLA.AC.UK _publ_section_title ; Supramolecular self-assembly and anion-dependence of copper(II) complexes with cationic Dihydro-Imidazo Phenanthridinium (DIP)- containing ligands ; loop_ _publ_author_name 'Leroy Cronin' 'Phil. J. Kitson' 'De-Liang Long.' 'Alexis D C Parenty' ; Yu-Fei Song ; 'Robert J Thatcher' # Attachment 'compound1.cif' data_ys026013 _database_code_depnum_ccdc_archive 'CCDC 678279' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C84 H71 B4 Br3 Cu F16 N12' _chemical_formula_weight 1899.04 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21/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 28.553(2) _cell_length_b 8.2201(6) _cell_length_c 16.7163(13) _cell_angle_alpha 90.00 _cell_angle_beta 100.746(3) _cell_angle_gamma 90.00 _cell_volume 3854.7(5) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 3386 _cell_measurement_theta_min 2.9 _cell_measurement_theta_max 21.4 _exptl_crystal_description block _exptl_crystal_colour green _exptl_crystal_size_max 0.14 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.636 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1914 _exptl_absorpt_coefficient_mu 1.934 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.7735 _exptl_absorpt_correction_T_max 0.8606 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _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 'Bruker Apex CCD' _diffrn_measurement_method '\w & \p scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% none _diffrn_reflns_number 23213 _diffrn_reflns_av_R_equivalents 0.0676 _diffrn_reflns_av_sigmaI/netI 0.0598 _diffrn_reflns_limit_h_min -29 _diffrn_reflns_limit_h_max 30 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.45 _diffrn_reflns_theta_max 22.18 _reflns_number_total 4747 _reflns_number_gt 3725 _reflns_threshold_expression >2sigma(I) _computing_data_collection Apex _computing_cell_refinement Apex _computing_data_reduction Apex _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics Mercury _computing_publication_material Wingx _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^)+(0.0000P)^2^+15.2444P] 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 SHELXL _refine_ls_extinction_coef 0.00048(8) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 4747 _refine_ls_number_parameters 562 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0805 _refine_ls_R_factor_gt 0.0590 _refine_ls_wR_factor_ref 0.1137 _refine_ls_wR_factor_gt 0.1068 _refine_ls_goodness_of_fit_ref 1.145 _refine_ls_restrained_S_all 1.145 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu 0.0000 0.5000 0.5000 0.0256(3) Uani 1 2 d S . . Br1 Br 0.05000(7) 0.67926(17) 0.59797(8) 0.0298(4) Uani 0.592(2) 1 d P A 1 Br1' Br 0.02164(10) 0.7034(2) 0.59975(11) 0.0246(5) Uani 0.408(2) 1 d P A 2 Br2 Br 0.13929(5) 0.72364(19) 0.65342(9) 0.0305(6) Uani 0.408(2) 1 d P A 2 Br3 Br 0.3626(5) -0.0255(18) 0.4423(8) 0.044(4) Uiso 0.05 1 d P B 2 B1 B 0.4130(3) 0.1882(9) 0.2465(4) 0.0273(18) Uani 1 1 d . . . B2 B 0.1381(3) 0.4249(10) 0.3803(5) 0.035(2) Uani 1 1 d . . . F1 F 0.39630(12) 0.2515(5) 0.16880(19) 0.0444(10) Uani 1 1 d . . . F2 F 0.45841(12) 0.1266(5) 0.2512(2) 0.0472(11) Uani 1 1 d . . . F3 F 0.38234(13) 0.0644(4) 0.2610(2) 0.0466(10) Uani 1 1 d . . . F4 F 0.41371(14) 0.3105(5) 0.3032(2) 0.0508(11) Uani 1 1 d . . . F5 F 0.17351(16) 0.3121(6) 0.3885(3) 0.0795(15) Uani 1 1 d . . . F6 F 0.09461(15) 0.3451(6) 0.3630(2) 0.0678(13) Uani 1 1 d . . . F7 F 0.14067(14) 0.5058(5) 0.4534(2) 0.0609(12) Uani 1 1 d . . . F8 F 0.1406(2) 0.5311(6) 0.3205(3) 0.1029(19) Uani 1 1 d . . . N1 N 0.17408(18) 0.0223(6) 0.5004(3) 0.0272(13) Uani 1 1 d . . . N2 N 0.11272(18) 0.1342(6) 0.5422(3) 0.0289(13) Uani 1 1 d . . . N3 N 0.00612(18) 0.3308(6) 0.5838(3) 0.0229(12) Uani 1 1 d . A . N4 N 0.34739(18) 0.7631(6) 0.6734(3) 0.0256(12) Uani 1 1 d . . . N5 N 0.41783(18) 0.7075(6) 0.6463(3) 0.0279(13) Uani 1 1 d . . . N6 N 0.43452(18) 0.8152(6) 0.4973(3) 0.0333(13) Uani 1 1 d . . . C7 C 0.2434(2) 0.1842(7) 0.6105(3) 0.0232(15) Uani 1 1 d . C . C11 C 0.1823(2) 0.2695(7) 0.6863(3) 0.0268(15) Uani 1 1 d . . . H11 H 0.1499 0.2717 0.6924 0.032 Uiso 1 1 calc R . . C23 C 0.2774(2) 0.8404(7) 0.7269(3) 0.0278(16) Uani 1 1 d . . . H23 H 0.2965 0.9036 0.7681 0.033 Uiso 1 1 calc R . . C22 C 0.2985(2) 0.7550(7) 0.6699(3) 0.0246(15) Uani 1 1 d . . . C12 C 0.1944(2) 0.1967(7) 0.6174(3) 0.0245(15) Uani 1 1 d . . . C5 C 0.3041(2) 0.0684(7) 0.5348(4) 0.0278(16) Uani 1 1 d . C 1 H5 H 0.3289 0.1231 0.5705 0.033 Uiso 1 1 calc R C 1 C34 C 0.3712(2) 0.6824(7) 0.6234(3) 0.0232(15) Uani 1 1 d . . . C38 C 0.4695(2) 0.7258(7) 0.5413(3) 0.0257(15) Uani 1 1 d . . . C3 C 0.2794(3) -0.1116(8) 0.4223(4) 0.0345(17) Uani 1 1 d . C 1 H3 H 0.2874 -0.1779 0.3803 0.041 Uiso 1 1 calc R C 1 C29 C 0.2686(2) 0.4901(7) 0.4846(3) 0.0302(16) Uani 1 1 d . . . H29 H 0.2350 0.4825 0.4793 0.036 Uiso 1 1 calc R . . C16 C 0.0855(2) 0.2775(7) 0.5581(4) 0.0329(16) Uani 1 1 d . A . H16A H 0.0715 0.3292 0.5055 0.039 Uiso 1 1 calc R . . H16B H 0.1075 0.3570 0.5900 0.039 Uiso 1 1 calc R . . C24 C 0.2287(2) 0.8321(7) 0.7228(4) 0.0316(17) Uani 1 1 d . A . H24 H 0.2143 0.8879 0.7617 0.038 Uiso 1 1 calc R . . C1 C 0.2214(2) 0.0023(7) 0.4923(3) 0.0263(15) Uani 1 1 d . C . C42 C 0.4451(3) 0.8879(8) 0.4301(4) 0.0360(18) Uani 1 1 d . . . H42 H 0.4213 0.9533 0.3980 0.043 Uiso 1 1 calc R . . C6 C 0.2568(2) 0.0884(7) 0.5452(3) 0.0240(15) Uani 1 1 d . . . C36 C 0.4271(2) 0.8336(8) 0.7096(4) 0.0332(17) Uani 1 1 d . . . H36A H 0.4357 0.9382 0.6868 0.040 Uiso 1 1 calc R . . H36B H 0.4531 0.8004 0.7544 0.040 Uiso 1 1 calc R . . C27 C 0.2709(2) 0.6621(7) 0.6086(3) 0.0237(15) Uani 1 1 d . . . C13 C 0.1604(2) 0.1223(7) 0.5546(4) 0.0277(16) Uani 1 1 d . . . C9 C 0.2641(2) 0.3366(7) 0.7359(4) 0.0315(17) Uani 1 1 d . C . H9 H 0.2874 0.3902 0.7749 0.038 Uiso 1 1 calc R . . C39 C 0.5144(2) 0.7088(8) 0.5227(4) 0.0350(17) Uani 1 1 d . . . H39 H 0.5385 0.6470 0.5563 0.042 Uiso 1 1 calc R . . C40 C 0.5230(3) 0.7861(8) 0.4524(4) 0.045(2) Uani 1 1 d . . . H40 H 0.5533 0.7784 0.4372 0.053 Uiso 1 1 calc R . . C31 C 0.3395(3) 0.4256(7) 0.4346(4) 0.0347(17) Uani 1 1 d . . . H31 H 0.3546 0.3733 0.3955 0.042 Uiso 1 1 calc R . . C37 C 0.4578(2) 0.6403(8) 0.6152(3) 0.0313(16) Uani 1 1 d . . . H37A H 0.4510 0.5247 0.6012 0.038 Uiso 1 1 calc R . . H37B H 0.4863 0.6437 0.6591 0.038 Uiso 1 1 calc R . . C18 C 0.0499(2) 0.1220(8) 0.6638(4) 0.0336(17) Uani 1 1 d . A . H18 H 0.0777 0.0565 0.6765 0.040 Uiso 1 1 calc R . . C10 C 0.2165(2) 0.3376(7) 0.7451(4) 0.0313(16) Uani 1 1 d . . . H10 H 0.2078 0.3854 0.7920 0.038 Uiso 1 1 calc R . . C19 C 0.0128(3) 0.1017(8) 0.7048(4) 0.0339(17) Uani 1 1 d . . . H19 H 0.0150 0.0226 0.7467 0.041 Uiso 1 1 calc R . . C8 C 0.2776(2) 0.2583(7) 0.6704(3) 0.0262(15) Uani 1 1 d . . . H8 H 0.3103 0.2549 0.6661 0.031 Uiso 1 1 calc R C . C2 C 0.2329(2) -0.0987(7) 0.4312(4) 0.0333(17) Uani 1 1 d . . . H2 H 0.2086 -0.1575 0.3963 0.040 Uiso 1 1 calc R C 1 C21 C -0.0292(2) 0.3075(7) 0.6243(3) 0.0281(16) Uani 1 1 d . . . H21 H -0.0571 0.3719 0.6103 0.034 Uiso 1 1 calc R A . C33 C 0.3443(2) 0.5870(7) 0.5569(3) 0.0229(15) Uani 1 1 d . . . C4 C 0.3150(2) -0.0283(8) 0.4744(4) 0.0339(17) Uani 1 1 d . C 1 H4 H 0.3473 -0.0387 0.4680 0.041 Uiso 1 1 calc R C 1 C20 C -0.0270(2) 0.1952(8) 0.6853(3) 0.0300(16) Uani 1 1 d . A . H20 H -0.0528 0.1827 0.7134 0.036 Uiso 1 1 calc R . . C32 C 0.3661(2) 0.5114(7) 0.4974(3) 0.0307(16) Uani 1 1 d . . . H32 H 0.3996 0.5201 0.5010 0.037 Uiso 1 1 calc R . . C26 C 0.2213(2) 0.6588(8) 0.6055(4) 0.0319(17) Uani 1 1 d . A . H26 H 0.2017 0.5981 0.5639 0.038 Uiso 1 1 calc R . . C28 C 0.2948(2) 0.5778(7) 0.5500(3) 0.0272(16) Uani 1 1 d . . . C25 C 0.2007(2) 0.7410(7) 0.6611(4) 0.0314(16) Uani 1 1 d . . . C30 C 0.2903(3) 0.4154(7) 0.4285(4) 0.0372(18) Uani 1 1 d . . . H30 H 0.2717 0.3561 0.3851 0.045 Uiso 1 1 calc R . . C17 C 0.0461(2) 0.2393(7) 0.6037(3) 0.0239(15) Uani 1 1 d . . . C14 C 0.1329(2) -0.0471(8) 0.4441(4) 0.0372(18) Uani 1 1 d . . . H14A H 0.1329 -0.1674 0.4470 0.045 Uiso 1 1 calc R . . H14B H 0.1328 -0.0132 0.3873 0.045 Uiso 1 1 calc R . . C35 C 0.3802(2) 0.8469(8) 0.7388(4) 0.0304(16) Uani 1 1 d . . . H35A H 0.3816 0.7917 0.7918 0.036 Uiso 1 1 calc R . . H35B H 0.3709 0.9619 0.7437 0.036 Uiso 1 1 calc R . . C15 C 0.0906(2) 0.0249(8) 0.4758(4) 0.0342(17) Uani 1 1 d . . . H15A H 0.0694 0.0862 0.4325 0.041 Uiso 1 1 calc R . . H15B H 0.0718 -0.0615 0.4966 0.041 Uiso 1 1 calc R . . C41 C 0.4871(3) 0.8729(8) 0.4061(4) 0.0383(18) Uani 1 1 d . . . H41 H 0.4919 0.9225 0.3569 0.046 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 0.0404(7) 0.0178(6) 0.0182(6) 0.0032(5) 0.0048(5) 0.0031(5) Br1 0.0385(11) 0.0273(7) 0.0225(7) 0.0005(5) 0.0029(7) -0.0049(8) Br1' 0.0265(13) 0.0267(11) 0.0200(9) -0.0017(7) 0.0032(10) -0.0028(10) Br2 0.0254(10) 0.0314(11) 0.0363(10) -0.0024(8) 0.0103(7) 0.0029(7) B1 0.031(5) 0.026(4) 0.026(4) -0.001(4) 0.012(4) 0.004(4) B2 0.040(5) 0.038(5) 0.031(5) 0.006(4) 0.016(4) 0.006(4) F1 0.034(2) 0.074(3) 0.026(2) 0.009(2) 0.0064(17) 0.000(2) F2 0.030(2) 0.058(3) 0.053(2) -0.009(2) 0.0043(19) 0.012(2) F3 0.043(2) 0.043(2) 0.052(2) 0.011(2) 0.004(2) -0.008(2) F4 0.076(3) 0.037(2) 0.039(2) -0.005(2) 0.011(2) 0.013(2) F5 0.063(3) 0.076(3) 0.093(4) -0.031(3) -0.004(3) 0.030(3) F6 0.055(3) 0.084(3) 0.061(3) -0.010(3) 0.001(2) -0.013(3) F7 0.054(3) 0.080(3) 0.052(3) -0.030(2) 0.016(2) -0.007(2) F8 0.142(5) 0.089(4) 0.087(4) 0.043(3) 0.044(3) -0.013(4) N1 0.036(4) 0.021(3) 0.023(3) -0.003(3) 0.000(3) -0.003(3) N2 0.025(3) 0.023(3) 0.037(3) -0.003(3) 0.001(3) 0.003(3) N3 0.035(3) 0.021(3) 0.012(3) 0.002(2) 0.003(2) 0.004(3) N4 0.032(3) 0.022(3) 0.020(3) -0.001(2) 0.000(3) -0.003(3) N5 0.035(4) 0.027(3) 0.023(3) -0.004(3) 0.008(3) -0.003(3) N6 0.038(3) 0.030(3) 0.031(3) 0.005(3) 0.004(3) -0.009(3) C7 0.030(4) 0.017(3) 0.022(3) 0.004(3) 0.005(3) 0.003(3) C11 0.027(4) 0.026(4) 0.028(4) 0.000(3) 0.007(3) -0.001(3) C23 0.037(4) 0.025(4) 0.022(3) 0.005(3) 0.005(3) -0.001(3) C22 0.039(4) 0.018(4) 0.017(3) 0.008(3) 0.007(3) 0.000(3) C12 0.032(4) 0.019(4) 0.021(3) 0.007(3) 0.000(3) 0.000(3) C5 0.037(4) 0.016(4) 0.031(4) 0.009(3) 0.008(3) 0.000(3) C34 0.033(4) 0.016(3) 0.022(3) 0.007(3) 0.010(3) 0.000(3) C38 0.037(4) 0.018(4) 0.021(3) -0.003(3) 0.005(3) -0.003(3) C3 0.048(5) 0.026(4) 0.034(4) 0.010(3) 0.019(4) 0.008(4) C29 0.044(4) 0.022(4) 0.025(3) 0.000(3) 0.007(3) -0.004(3) C16 0.032(4) 0.028(4) 0.039(4) 0.006(3) 0.006(3) 0.005(3) C24 0.045(5) 0.027(4) 0.028(4) 0.008(3) 0.019(3) 0.005(3) C1 0.034(4) 0.020(4) 0.025(3) 0.008(3) 0.004(3) 0.008(3) C42 0.049(5) 0.032(4) 0.027(4) 0.003(3) 0.006(4) -0.008(4) C6 0.029(4) 0.015(3) 0.027(4) 0.008(3) 0.002(3) 0.001(3) C36 0.032(4) 0.036(4) 0.031(4) -0.006(3) 0.004(3) -0.001(3) C27 0.035(4) 0.017(3) 0.021(3) 0.008(3) 0.010(3) 0.002(3) C13 0.040(5) 0.019(4) 0.026(4) 0.005(3) 0.008(3) -0.001(3) C9 0.052(5) 0.018(4) 0.022(4) 0.004(3) 0.002(3) -0.007(3) C39 0.036(5) 0.026(4) 0.046(4) -0.005(3) 0.018(3) 0.003(3) C40 0.053(5) 0.028(4) 0.062(5) -0.021(4) 0.034(4) -0.009(4) C31 0.058(5) 0.023(4) 0.028(4) -0.001(3) 0.022(4) -0.003(4) C37 0.035(4) 0.032(4) 0.029(4) -0.003(3) 0.010(3) -0.001(3) C18 0.036(4) 0.033(4) 0.029(4) 0.007(3) 0.002(3) 0.005(3) C10 0.040(5) 0.027(4) 0.028(4) 0.001(3) 0.009(3) 0.002(3) C19 0.057(5) 0.025(4) 0.018(3) 0.007(3) 0.003(4) -0.005(4) C8 0.032(4) 0.021(4) 0.026(4) 0.009(3) 0.007(3) 0.001(3) C2 0.049(5) 0.021(4) 0.026(4) 0.000(3) -0.002(3) 0.003(3) C21 0.040(4) 0.025(4) 0.020(3) -0.004(3) 0.008(3) 0.001(3) C33 0.035(4) 0.014(3) 0.020(3) 0.000(3) 0.008(3) -0.005(3) C4 0.042(4) 0.029(4) 0.037(4) 0.008(4) 0.022(4) 0.006(4) C20 0.037(4) 0.036(4) 0.019(3) 0.002(3) 0.010(3) -0.010(4) C32 0.044(4) 0.023(4) 0.028(4) 0.005(3) 0.013(3) -0.001(3) C26 0.045(5) 0.027(4) 0.022(4) 0.003(3) 0.003(3) -0.006(3) C28 0.045(5) 0.014(3) 0.023(4) 0.008(3) 0.007(3) 0.000(3) C25 0.044(4) 0.021(4) 0.029(4) 0.004(3) 0.007(3) -0.001(3) C30 0.068(6) 0.018(4) 0.026(4) 0.002(3) 0.011(4) -0.009(4) C17 0.035(4) 0.016(3) 0.019(3) 0.005(3) 0.001(3) -0.005(3) C14 0.038(4) 0.030(4) 0.039(4) -0.003(3) -0.004(3) -0.006(3) C35 0.034(4) 0.028(4) 0.031(4) -0.004(3) 0.009(3) -0.004(3) C15 0.034(4) 0.028(4) 0.037(4) -0.002(3) 0.000(3) -0.004(3) C41 0.059(5) 0.029(4) 0.031(4) -0.007(3) 0.020(4) -0.006(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 N3 1.959(4) 3_566 ? Cu1 N3 1.959(4) . ? Cu1 Br1' 2.3605(18) 3_566 ? Cu1 Br1' 2.3605(18) . ? Cu1 Br1 2.4534(14) 3_566 ? Cu1 Br1 2.4534(14) . ? Br2 C25 1.739(7) . ? B1 F2 1.379(8) . ? B1 F4 1.380(8) . ? B1 F3 1.393(8) . ? B1 F1 1.398(7) . ? B2 F8 1.339(8) . ? B2 F5 1.360(9) . ? B2 F7 1.382(8) . ? B2 F6 1.387(9) . ? N1 C13 1.335(7) . ? N1 C1 1.391(7) . ? N1 C14 1.476(7) . ? N2 C13 1.342(7) . ? N2 C16 1.463(7) . ? N2 C15 1.475(7) . ? N3 C21 1.328(7) . ? N3 C17 1.356(7) . ? N4 C34 1.346(7) . ? N4 C22 1.388(7) . ? N4 C35 1.471(7) . ? N5 C34 1.332(7) . ? N5 C37 1.449(7) . ? N5 C36 1.469(7) . ? N6 C38 1.343(7) . ? N6 C42 1.356(8) . ? C7 C8 1.401(8) . ? C7 C12 1.428(8) . ? C7 C6 1.453(8) . ? C11 C10 1.369(8) . ? C11 C12 1.398(8) . ? C23 C24 1.379(8) . ? C23 C22 1.407(8) . ? C22 C27 1.397(8) . ? C12 C13 1.427(8) . ? C5 C4 1.367(8) . ? C5 C6 1.403(8) . ? C34 C33 1.456(8) . ? C38 C39 1.382(8) . ? C38 C37 1.512(8) . ? C3 C2 1.367(8) . ? C3 C4 1.391(9) . ? C29 C30 1.361(8) . ? C29 C28 1.404(8) . ? C16 C17 1.505(8) . ? C24 C25 1.400(8) . ? C1 C2 1.403(8) . ? C1 C6 1.404(8) . ? C42 C41 1.341(9) . ? C36 C35 1.512(8) . ? C27 C26 1.409(8) . ? C27 C28 1.466(8) . ? C9 C8 1.386(8) . ? C9 C10 1.395(8) . ? C39 C40 1.396(9) . ? C40 C41 1.365(9) . ? C31 C32 1.370(8) . ? C31 C30 1.394(9) . ? C18 C19 1.376(8) . ? C18 C17 1.382(8) . ? C19 C20 1.361(8) . ? C21 C20 1.369(8) . ? C33 C28 1.399(8) . ? C33 C32 1.413(8) . ? C26 C25 1.366(8) . ? C14 C15 1.528(8) . ? 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 N3 Cu1 N3 180.000(1) 3_566 . ? N3 Cu1 Br1' 91.21(14) 3_566 3_566 ? N3 Cu1 Br1' 88.79(14) . 3_566 ? N3 Cu1 Br1' 88.79(14) 3_566 . ? N3 Cu1 Br1' 91.21(14) . . ? Br1' Cu1 Br1' 180.0 3_566 . ? N3 Cu1 Br1 89.20(14) 3_566 3_566 ? N3 Cu1 Br1 90.80(14) . 3_566 ? Br1' Cu1 Br1 19.97(4) 3_566 3_566 ? Br1' Cu1 Br1 160.03(4) . 3_566 ? N3 Cu1 Br1 90.80(14) 3_566 . ? N3 Cu1 Br1 89.20(14) . . ? Br1' Cu1 Br1 160.03(4) 3_566 . ? Br1' Cu1 Br1 19.97(4) . . ? Br1 Cu1 Br1 180.0 3_566 . ? F2 B1 F4 109.6(6) . . ? F2 B1 F3 109.7(5) . . ? F4 B1 F3 109.9(5) . . ? F2 B1 F1 110.1(5) . . ? F4 B1 F1 109.0(5) . . ? F3 B1 F1 108.5(5) . . ? F8 B2 F5 112.2(7) . . ? F8 B2 F7 110.2(7) . . ? F5 B2 F7 108.9(6) . . ? F8 B2 F6 108.9(6) . . ? F5 B2 F6 108.6(6) . . ? F7 B2 F6 108.0(6) . . ? C13 N1 C1 123.4(5) . . ? C13 N1 C14 111.8(5) . . ? C1 N1 C14 124.3(5) . . ? C13 N2 C16 126.1(5) . . ? C13 N2 C15 110.6(5) . . ? C16 N2 C15 117.3(5) . . ? C21 N3 C17 118.6(5) . . ? C21 N3 Cu1 119.4(4) . . ? C17 N3 Cu1 121.9(4) . . ? C34 N4 C22 124.7(5) . . ? C34 N4 C35 111.5(5) . . ? C22 N4 C35 123.4(5) . . ? C34 N5 C37 130.6(5) . . ? C34 N5 C36 110.6(5) . . ? C37 N5 C36 118.6(5) . . ? C38 N6 C42 115.9(6) . . ? C8 C7 C12 118.3(5) . . ? C8 C7 C6 121.8(6) . . ? C12 C7 C6 119.9(5) . . ? C10 C11 C12 120.9(6) . . ? C24 C23 C22 119.7(6) . . ? N4 C22 C27 118.8(5) . . ? N4 C22 C23 120.1(5) . . ? C27 C22 C23 121.1(6) . . ? C11 C12 C13 123.3(6) . . ? C11 C12 C7 119.6(5) . . ? C13 C12 C7 116.9(5) . . ? C4 C5 C6 121.2(6) . . ? N5 C34 N4 109.8(5) . . ? N5 C34 C33 131.3(6) . . ? N4 C34 C33 119.0(6) . . ? N6 C38 C39 124.0(6) . . ? N6 C38 C37 116.5(6) . . ? C39 C38 C37 119.5(6) . . ? C2 C3 C4 120.4(6) . . ? C30 C29 C28 121.6(6) . . ? N2 C16 C17 113.4(5) . . ? C23 C24 C25 119.7(6) . . ? N1 C1 C2 120.3(6) . . ? N1 C1 C6 118.5(5) . . ? C2 C1 C6 121.2(6) . . ? C41 C42 N6 123.9(6) . . ? C5 C6 C1 117.4(6) . . ? C5 C6 C7 123.4(6) . . ? C1 C6 C7 119.1(6) . . ? N5 C36 C35 103.4(5) . . ? C22 C27 C26 117.5(5) . . ? C22 C27 C28 118.7(6) . . ? C26 C27 C28 123.8(5) . . ? N1 C13 N2 110.9(5) . . ? N1 C13 C12 121.2(6) . . ? N2 C13 C12 127.9(6) . . ? C8 C9 C10 120.7(6) . . ? C38 C39 C40 117.3(6) . . ? C41 C40 C39 119.0(7) . . ? C32 C31 C30 119.5(6) . . ? N5 C37 C38 115.2(5) . . ? C19 C18 C17 118.9(6) . . ? C11 C10 C9 119.8(6) . . ? C20 C19 C18 120.0(6) . . ? C9 C8 C7 120.5(6) . . ? C3 C2 C1 119.3(6) . . ? N3 C21 C20 123.0(6) . . ? C28 C33 C32 119.3(5) . . ? C28 C33 C34 118.2(5) . . ? C32 C33 C34 122.4(6) . . ? C5 C4 C3 120.5(6) . . ? C19 C20 C21 118.6(6) . . ? C31 C32 C33 120.9(6) . . ? C25 C26 C27 121.6(6) . . ? C33 C28 C29 118.3(6) . . ? C33 C28 C27 120.5(5) . . ? C29 C28 C27 121.1(6) . . ? C26 C25 C24 120.4(6) . . ? C26 C25 Br2 117.7(5) . . ? C24 C25 Br2 121.9(5) . . ? C29 C30 C31 120.3(6) . . ? N3 C17 C18 120.9(6) . . ? N3 C17 C16 115.8(5) . . ? C18 C17 C16 123.3(6) . . ? N1 C14 C15 102.5(5) . . ? N4 C35 C36 101.9(5) . . ? N2 C15 C14 103.9(5) . . ? C42 C41 C40 119.8(7) . . ? _diffrn_measured_fraction_theta_max 0.981 _diffrn_reflns_theta_full 22.18 _diffrn_measured_fraction_theta_full 0.981 _refine_diff_density_max 0.55 _refine_diff_density_min -0.42 _refine_diff_density_rms 0.07 # Attachment 'compound2.cif' data_ys02701 _database_code_depnum_ccdc_archive 'CCDC 678280' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C21 H18 Br2 Cu N4 O3' _chemical_formula_weight 597.75 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 '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' 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' _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 8.8546(5) _cell_length_b 11.6779(7) _cell_length_c 12.0660(7) _cell_angle_alpha 63.335(3) _cell_angle_beta 76.612(3) _cell_angle_gamma 78.007(3) _cell_volume 1076.90(11) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 6539 _cell_measurement_theta_min 2.4 _cell_measurement_theta_max 25.6 _exptl_crystal_description Block _exptl_crystal_colour green _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.843 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 590 _exptl_absorpt_coefficient_mu 4.756 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.2521 _exptl_absorpt_correction_T_max 0.7634 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _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 'Bruker Apex CCD' _diffrn_measurement_method '\w & \p scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% none _diffrn_reflns_number 16793 _diffrn_reflns_av_R_equivalents 0.0378 _diffrn_reflns_av_sigmaI/netI 0.0406 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.91 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3787 _reflns_number_gt 3088 _reflns_threshold_expression >2sigma(I) _computing_data_collection Apex _computing_cell_refinement Apex _computing_data_reduction Apex _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics Mercury _computing_publication_material Wingx _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^)+(0.0408P)^2^+5.6902P] 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 SHELXL _refine_ls_extinction_coef none _refine_ls_extinction_expression none _refine_ls_number_reflns 3787 _refine_ls_number_parameters 286 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0581 _refine_ls_R_factor_gt 0.0425 _refine_ls_wR_factor_ref 0.1056 _refine_ls_wR_factor_gt 0.0975 _refine_ls_goodness_of_fit_ref 1.018 _refine_ls_restrained_S_all 1.018 _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 0.98344(7) 0.65678(7) 0.57695(6) 0.0256(2) Uani 1 1 d . . . Br1 Br 1.11065(6) 0.65127(6) 0.37964(5) 0.02684(19) Uani 1 1 d . . . Br2 Br 0.86189(6) 0.57038(7) 0.79329(5) 0.0275(3) Uani 0.946(3) 1 d P . . Br2' Br 0.8639(15) 0.6699(16) 0.7522(13) 0.045(5) Uiso 0.054(3) 1 d P . . O1 O 0.6783(5) 0.9178(4) 0.4017(5) 0.0536(13) Uani 1 1 d . . . O2 O 0.7818(4) 0.7253(4) 0.5109(4) 0.0325(10) Uani 1 1 d . . . O3 O 0.8850(5) 0.8910(4) 0.4837(5) 0.0456(12) Uani 1 1 d . . . N1 N 1.4433(5) 0.1017(5) 0.8065(4) 0.0232(10) Uani 1 1 d . . . N2 N 1.3569(5) 0.3100(4) 0.7194(4) 0.0243(10) Uani 1 1 d . . . N3 N 1.1845(5) 0.6503(4) 0.6271(4) 0.0223(10) Uani 1 1 d . . . N4 N 0.7795(5) 0.8498(4) 0.4661(5) 0.0300(11) Uani 1 1 d . . . C1 C 1.4351(6) -0.0295(5) 0.8834(5) 0.0237(12) Uani 1 1 d . . . C2 C 1.5492(6) -0.1246(6) 0.8621(5) 0.0293(13) Uani 1 1 d . . . H2 H 1.6387 -0.1004 0.7996 0.035 Uiso 1 1 calc R . . C3 C 1.5299(7) -0.2522(6) 0.9325(5) 0.0303(13) Uani 1 1 d . . . H3 H 1.6072 -0.3163 0.9188 0.036 Uiso 1 1 calc R . . C4 C 1.3990(7) -0.2895(6) 1.0236(6) 0.0316(13) Uani 1 1 d . . . H4 H 1.3843 -0.3781 1.0686 0.038 Uiso 1 1 calc R . . C5 C 1.2901(6) -0.1966(6) 1.0484(5) 0.0280(13) Uani 1 1 d . . . H5 H 1.2025 -0.2228 1.1125 0.034 Uiso 1 1 calc R . . C6 C 1.3061(6) -0.0639(5) 0.9807(5) 0.0226(12) Uani 1 1 d . . . C7 C 1.2002(6) 0.0376(5) 1.0080(5) 0.0226(12) Uani 1 1 d . . . C8 C 1.0865(6) 0.0074(6) 1.1170(5) 0.0260(12) Uani 1 1 d . . . H8 H 1.0725 -0.0802 1.1706 0.031 Uiso 1 1 calc R . . C9 C 0.9958(6) 0.1040(6) 1.1461(5) 0.0301(14) Uani 1 1 d . . . H9 H 0.9188 0.0824 1.2195 0.036 Uiso 1 1 calc R . . C10 C 1.0152(6) 0.2334(6) 1.0695(5) 0.0304(13) Uani 1 1 d . . . H10 H 0.9532 0.2989 1.0919 0.036 Uiso 1 1 calc R . . C11 C 1.1234(6) 0.2663(6) 0.9618(5) 0.0253(12) Uani 1 1 d . . . H11 H 1.1371 0.3544 0.9102 0.030 Uiso 1 1 calc R . . C12 C 1.2145(6) 0.1689(5) 0.9278(5) 0.0212(12) Uani 1 1 d . . . C13 C 1.3349(6) 0.1974(5) 0.8171(5) 0.0217(12) Uani 1 1 d . . . C14 C 1.5625(6) 0.1522(5) 0.6942(5) 0.0279(13) Uani 1 1 d . . . H14A H 1.5764 0.1046 0.6416 0.033 Uiso 1 1 calc R . . H14B H 1.6644 0.1476 0.7175 0.033 Uiso 1 1 calc R . . C15 C 1.4920(6) 0.2917(6) 0.6273(5) 0.0314(14) Uani 1 1 d . . . H15A H 1.5688 0.3521 0.6057 0.038 Uiso 1 1 calc R . . H15B H 1.4572 0.3056 0.5494 0.038 Uiso 1 1 calc R . . C16 C 1.2424(6) 0.4218(5) 0.6746(5) 0.0253(12) Uani 1 1 d . . . H16A H 1.1399 0.4017 0.7285 0.030 Uiso 1 1 calc R . . H16B H 1.2313 0.4400 0.5882 0.030 Uiso 1 1 calc R . . C17 C 1.2838(6) 0.5416(5) 0.6736(5) 0.0231(12) Uani 1 1 d . . . C18 C 1.4177(6) 0.5442(6) 0.7142(5) 0.0250(12) Uani 1 1 d . . . H18 H 1.4866 0.4673 0.7475 0.030 Uiso 1 1 calc R . . C19 C 1.4497(6) 0.6591(6) 0.7057(5) 0.0285(13) Uani 1 1 d . . . H19 H 1.5409 0.6614 0.7330 0.034 Uiso 1 1 calc R . . C20 C 1.3490(6) 0.7702(6) 0.6575(5) 0.0280(13) Uani 1 1 d . . . H20 H 1.3694 0.8500 0.6506 0.034 Uiso 1 1 calc R . . C21 C 1.2165(6) 0.7618(6) 0.6191(5) 0.0252(12) Uani 1 1 d . . . H21 H 1.1460 0.8377 0.5860 0.030 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 0.0145(3) 0.0380(5) 0.0252(4) -0.0122(3) -0.0059(3) -0.0045(3) Br1 0.0234(3) 0.0362(4) 0.0199(3) -0.0069(2) -0.0032(2) -0.0133(2) Br2 0.0163(3) 0.0398(5) 0.0262(3) -0.0155(3) -0.0010(2) -0.0020(2) O1 0.046(3) 0.042(3) 0.071(3) -0.010(3) -0.039(3) 0.001(2) O2 0.024(2) 0.033(3) 0.039(2) -0.010(2) -0.0130(17) -0.0038(17) O3 0.038(3) 0.039(3) 0.067(3) -0.019(2) -0.027(2) -0.006(2) N1 0.013(2) 0.039(3) 0.021(2) -0.016(2) -0.0012(17) -0.0049(19) N2 0.017(2) 0.033(3) 0.021(2) -0.009(2) -0.0032(18) -0.0059(19) N3 0.015(2) 0.034(3) 0.020(2) -0.012(2) -0.0026(17) -0.0055(19) N4 0.017(2) 0.021(3) 0.046(3) -0.002(2) -0.018(2) -0.0019(19) C1 0.021(3) 0.029(3) 0.026(3) -0.013(3) -0.010(2) -0.003(2) C2 0.017(3) 0.046(4) 0.031(3) -0.022(3) -0.008(2) 0.001(2) C3 0.032(3) 0.027(3) 0.038(3) -0.018(3) -0.015(3) 0.003(3) C4 0.034(3) 0.031(3) 0.035(3) -0.014(3) -0.010(3) -0.006(3) C5 0.027(3) 0.037(4) 0.024(3) -0.013(3) -0.008(2) -0.006(3) C6 0.019(3) 0.032(3) 0.021(3) -0.014(2) -0.006(2) -0.004(2) C7 0.020(3) 0.032(3) 0.018(3) -0.010(2) -0.006(2) -0.007(2) C8 0.024(3) 0.035(3) 0.020(3) -0.009(2) -0.006(2) -0.006(2) C9 0.021(3) 0.049(4) 0.022(3) -0.016(3) 0.000(2) -0.008(3) C10 0.024(3) 0.039(4) 0.032(3) -0.021(3) 0.000(2) -0.002(3) C11 0.022(3) 0.029(3) 0.025(3) -0.010(2) -0.006(2) -0.004(2) C12 0.016(2) 0.032(3) 0.021(3) -0.014(2) -0.005(2) -0.004(2) C13 0.012(2) 0.033(3) 0.023(3) -0.012(3) -0.005(2) -0.005(2) C14 0.018(3) 0.033(3) 0.030(3) -0.013(3) 0.003(2) -0.009(2) C15 0.020(3) 0.048(4) 0.026(3) -0.014(3) 0.004(2) -0.016(3) C16 0.020(3) 0.032(3) 0.022(3) -0.005(2) -0.006(2) -0.011(2) C17 0.016(3) 0.034(3) 0.017(3) -0.008(2) 0.000(2) -0.007(2) C18 0.016(3) 0.035(3) 0.024(3) -0.010(3) -0.004(2) -0.006(2) C19 0.016(3) 0.049(4) 0.027(3) -0.020(3) -0.005(2) -0.007(3) C20 0.022(3) 0.038(4) 0.029(3) -0.018(3) -0.002(2) -0.007(3) C21 0.016(3) 0.037(4) 0.022(3) -0.012(3) -0.004(2) -0.001(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 N3 1.986(4) . ? Cu1 O2 1.989(4) . ? Cu1 O3 2.492(4) . ? Cu1 Br2' 2.192(13) . ? Cu1 Br2 2.4035(9) . ? Cu1 Br1 2.4097(8) . ? Br2 Br2' 1.042(16) . ? O1 N4 1.228(6) . ? O2 N4 1.301(6) . ? O3 N4 1.233(6) . ? N1 C13 1.346(7) . ? N1 C1 1.397(7) . ? N1 C14 1.476(6) . ? N2 C13 1.328(7) . ? N2 C16 1.448(7) . ? N2 C15 1.484(7) . ? N3 C21 1.347(7) . ? N3 C17 1.350(7) . ? C1 C2 1.411(8) . ? C1 C6 1.411(7) . ? C2 C3 1.368(8) . ? C3 C4 1.390(8) . ? C4 C5 1.385(8) . ? C5 C6 1.410(8) . ? C6 C7 1.462(7) . ? C7 C8 1.409(7) . ? C7 C12 1.413(8) . ? C8 C9 1.375(8) . ? C9 C10 1.395(8) . ? C10 C11 1.372(8) . ? C11 C12 1.413(7) . ? C12 C13 1.455(7) . ? C14 C15 1.524(8) . ? C16 C17 1.513(8) . ? C17 C18 1.393(7) . ? C18 C19 1.383(8) . ? C19 C20 1.378(8) . ? C20 C21 1.392(7) . ? 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 N3 Cu1 O2 160.88(18) . . ? N3 Cu1 Br2' 88.0(4) . . ? O2 Cu1 Br2' 88.4(4) . . ? N3 Cu1 Br2 90.64(12) . . ? O2 Cu1 Br2 94.22(12) . . ? Br2' Cu1 Br2 25.7(4) . . ? N3 Cu1 Br1 92.79(12) . . ? O2 Cu1 Br1 90.14(12) . . ? Br2' Cu1 Br1 177.7(4) . . ? Br2 Cu1 Br1 156.40(4) . . ? Br2' Br2 Cu1 65.7(7) . . ? Br2 Br2' Cu1 88.6(8) . . ? N4 O2 Cu1 103.4(3) . . ? C13 N1 C1 124.6(4) . . ? C13 N1 C14 111.0(4) . . ? C1 N1 C14 124.0(4) . . ? C13 N2 C16 127.6(4) . . ? C13 N2 C15 109.6(4) . . ? C16 N2 C15 118.0(4) . . ? C21 N3 C17 119.4(4) . . ? C21 N3 Cu1 116.2(3) . . ? C17 N3 Cu1 124.3(4) . . ? O1 N4 O3 124.6(5) . . ? O1 N4 O2 117.4(4) . . ? O3 N4 O2 117.8(4) . . ? N1 C1 C2 121.2(5) . . ? N1 C1 C6 117.7(5) . . ? C2 C1 C6 121.0(5) . . ? C3 C2 C1 119.4(5) . . ? C2 C3 C4 121.1(5) . . ? C5 C4 C3 119.6(6) . . ? C4 C5 C6 121.6(5) . . ? C5 C6 C1 117.1(5) . . ? C5 C6 C7 123.9(5) . . ? C1 C6 C7 119.0(5) . . ? C8 C7 C12 118.5(5) . . ? C8 C7 C6 121.1(5) . . ? C12 C7 C6 120.3(4) . . ? C9 C8 C7 120.4(5) . . ? C8 C9 C10 120.9(5) . . ? C11 C10 C9 120.2(5) . . ? C10 C11 C12 119.9(5) . . ? C7 C12 C11 120.0(5) . . ? C7 C12 C13 117.4(5) . . ? C11 C12 C13 122.4(5) . . ? N2 C13 N1 111.9(4) . . ? N2 C13 C12 128.7(5) . . ? N1 C13 C12 119.4(5) . . ? N1 C14 C15 102.1(4) . . ? N2 C15 C14 104.4(4) . . ? N2 C16 C17 113.6(4) . . ? N3 C17 C18 120.5(5) . . ? N3 C17 C16 116.0(4) . . ? C18 C17 C16 123.5(5) . . ? C19 C18 C17 119.7(5) . . ? C20 C19 C18 119.9(5) . . ? C19 C20 C21 118.0(6) . . ? N3 C21 C20 122.5(5) . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 2.23 _refine_diff_density_min -0.65 _refine_diff_density_rms 0.12 # Attachment 'compound3.cif' data_ys03701 _database_code_depnum_ccdc_archive 'CCDC 678281' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C21 H18 Br3 Cu N3' _chemical_formula_weight 615.65 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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' _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 11.867(4) _cell_length_b 13.477(5) _cell_length_c 14.980(5) _cell_angle_alpha 106.773(8) _cell_angle_beta 104.342(8) _cell_angle_gamma 100.370(8) _cell_volume 2139.1(12) _cell_formula_units_Z 4 _cell_measurement_temperature 273(2) _cell_measurement_reflns_used 1012 _cell_measurement_theta_min 2.6 _cell_measurement_theta_max 21.9 _exptl_crystal_description block _exptl_crystal_colour brown _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.912 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1196 _exptl_absorpt_coefficient_mu 6.637 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.2773 _exptl_absorpt_correction_T_max 0.6915 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 273(2) _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 'Bruker Apex CCD' _diffrn_measurement_method '\w & \p' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% none _diffrn_reflns_number 5690 _diffrn_reflns_av_R_equivalents 0.0435 _diffrn_reflns_av_sigmaI/netI 0.0952 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.50 _diffrn_reflns_theta_max 23.00 _reflns_number_total 4038 _reflns_number_gt 2906 _reflns_threshold_expression >2sigma(I) _computing_data_collection Apex _computing_cell_refinement Apex _computing_data_reduction Apex _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics Mercury _computing_publication_material Wingx _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^)+(0.1403P)^2^+38.0577P] 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 SHELXL _refine_ls_extinction_coef none _refine_ls_extinction_expression none _refine_ls_number_reflns 4038 _refine_ls_number_parameters 266 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1098 _refine_ls_R_factor_gt 0.0810 _refine_ls_wR_factor_ref 0.2489 _refine_ls_wR_factor_gt 0.2231 _refine_ls_goodness_of_fit_ref 1.054 _refine_ls_restrained_S_all 1.054 _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 0.7934(2) 0.25910(19) 0.72892(18) 0.0214(8) Uani 1 1 d . . . Cu2 Cu 0.5246(2) 0.6016(2) 0.80023(18) 0.0193(8) Uani 1 1 d . . . Br1 Br 0.90607(19) 0.38593(18) 0.67788(17) 0.0326(8) Uani 1 1 d . . . Br2 Br 0.76573(17) 0.06945(16) 0.69546(16) 0.0245(7) Uani 1 1 d . . . Br3 Br 0.59272(17) 0.25763(17) 0.65377(16) 0.0261(7) Uani 1 1 d . . . Br4 Br 0.70240(17) 0.72114(17) 0.80093(16) 0.0261(7) Uani 1 1 d . . . Br5 Br 0.61006(18) 0.50996(17) 0.89779(16) 0.0266(7) Uani 1 1 d . . . Br6 Br 0.35882(19) 0.62898(18) 0.86028(17) 0.0281(7) Uani 1 1 d . . . N1 N 1.3448(13) 0.1823(12) 0.8699(11) 0.017(4) Uiso 1 1 d . . . N2 N 1.1882(13) 0.2519(12) 0.8591(11) 0.015(4) Uiso 1 1 d . . . N3 N 0.9012(14) 0.3105(13) 0.8704(12) 0.019(4) Uiso 1 1 d . . . N4 N 0.3063(13) 0.9414(12) 0.6018(11) 0.017(4) Uiso 1 1 d . . . N5 N 0.3729(13) 0.8059(12) 0.6231(11) 0.015(4) Uiso 1 1 d . . . N6 N 0.4326(14) 0.5551(13) 0.6556(12) 0.023(4) Uiso 1 1 d . . . C1 C 1.4124(16) 0.1077(15) 0.8763(14) 0.016(5) Uiso 1 1 d . . . C2 C 1.532(2) 0.133(2) 0.8776(17) 0.037(6) Uiso 1 1 d . . . H2 H 1.5686 0.2003 0.8772 0.044 Uiso 1 1 calc R . . C3 C 1.594(2) 0.058(2) 0.8795(18) 0.045(7) Uiso 1 1 d . . . H3 H 1.6735 0.0730 0.8795 0.054 Uiso 1 1 calc R . . C4 C 1.540(2) -0.0432(19) 0.8814(16) 0.035(6) Uiso 1 1 d . . . H4 H 1.5836 -0.0933 0.8852 0.042 Uiso 1 1 calc R . . C5 C 1.4247(18) -0.0652(18) 0.8776(15) 0.028(5) Uiso 1 1 d . . . H5 H 1.3887 -0.1333 0.8760 0.034 Uiso 1 1 calc R . . C6 C 1.3532(18) 0.0083(17) 0.8758(15) 0.024(5) Uiso 1 1 d . . . C7 C 1.2314(16) -0.0125(15) 0.8796(14) 0.016(5) Uiso 1 1 d . . . C8 C 1.1682(18) -0.1059(17) 0.8874(15) 0.025(5) Uiso 1 1 d . . . H8 H 1.2074 -0.1592 0.8909 0.030 Uiso 1 1 calc R . . C9 C 1.055(2) -0.1234(19) 0.8902(16) 0.034(6) Uiso 1 1 d . . . H9 H 1.0181 -0.1883 0.8938 0.040 Uiso 1 1 calc R . . C10 C 0.9919(19) -0.0449(17) 0.8877(15) 0.028(6) Uiso 1 1 d . . . H10 H 0.9133 -0.0562 0.8904 0.034 Uiso 1 1 calc R . . C11 C 1.0521(18) 0.0515(17) 0.8808(15) 0.025(5) Uiso 1 1 d . . . H11 H 1.0134 0.1057 0.8813 0.030 Uiso 1 1 calc R . . C12 C 1.1684(15) 0.0677(14) 0.8734(13) 0.011(4) Uiso 1 1 d . . . C13 C 1.2295(17) 0.1659(16) 0.8664(14) 0.019(5) Uiso 1 1 d . . . C14 C 1.3957(17) 0.2898(16) 0.8706(15) 0.022(5) Uiso 1 1 d . . . H14A H 1.4365 0.2864 0.8215 0.026 Uiso 1 1 calc R . . H14B H 1.4521 0.3353 0.9347 0.026 Uiso 1 1 calc R . . C15 C 1.2849(17) 0.3302(16) 0.8459(16) 0.023(5) Uiso 1 1 d . . . H15A H 1.2982 0.4028 0.8902 0.027 Uiso 1 1 calc R . . H15B H 1.2635 0.3293 0.7788 0.027 Uiso 1 1 calc R . . C16 C 1.0623(16) 0.2534(16) 0.8255(14) 0.017(5) Uiso 1 1 d . . . H16A H 1.0134 0.1797 0.7899 0.021 Uiso 1 1 calc R . . H16B H 1.0548 0.2913 0.7793 0.021 Uiso 1 1 calc R . . C17 C 1.0096(17) 0.3042(16) 0.9039(14) 0.020(5) Uiso 1 1 d . . . C18 C 1.0760(17) 0.3433(15) 1.0053(14) 0.018(5) Uiso 1 1 d . . . H18 H 1.1542 0.3374 1.0272 0.022 Uiso 1 1 calc R . . C19 C 1.0206(17) 0.3903(16) 1.0700(16) 0.023(5) Uiso 1 1 d . . . H19 H 1.0607 0.4159 1.1373 0.027 Uiso 1 1 calc R . . C20 C 0.9052(19) 0.3993(17) 1.0347(16) 0.029(5) Uiso 1 1 d . . . H20 H 0.8669 0.4325 1.0773 0.034 Uiso 1 1 calc R . . C21 C 0.8468(17) 0.3562(15) 0.9313(14) 0.014(4) Uiso 1 1 d . . . H21 H 0.7685 0.3602 0.9061 0.017 Uiso 1 1 calc R . . C22 C 0.2325(17) 1.0131(16) 0.6011(14) 0.019(5) Uiso 1 1 d . . . C23 C 0.2675(18) 1.1047(16) 0.5816(15) 0.023(5) Uiso 1 1 d . . . H23 H 0.3397 1.1203 0.5679 0.028 Uiso 1 1 calc R . . C24 C 0.1958(19) 1.1729(18) 0.5822(16) 0.031(6) Uiso 1 1 d . . . H24 H 0.2184 1.2354 0.5689 0.038 Uiso 1 1 calc R . . C25 C 0.0891(18) 1.1485(17) 0.6030(15) 0.023(5) Uiso 1 1 d . . . H25 H 0.0407 1.1958 0.6050 0.028 Uiso 1 1 calc R . . C26 C 0.0534(18) 1.0535(16) 0.6210(14) 0.021(5) Uiso 1 1 d . . . H26 H -0.0193 1.0367 0.6335 0.025 Uiso 1 1 calc R . . C27 C 0.1248(17) 0.9866(16) 0.6200(14) 0.017(5) Uiso 1 1 d . . . C28 C 0.0885(17) 0.8784(16) 0.6302(15) 0.021(5) Uiso 1 1 d . . . C29 C -0.0228(19) 0.8444(17) 0.6456(15) 0.027(5) Uiso 1 1 d . . . H29 H -0.0722 0.8906 0.6517 0.033 Uiso 1 1 calc R . . C30 C -0.0587(19) 0.7461(16) 0.6516(15) 0.025(5) Uiso 1 1 d . . . H30 H -0.1308 0.7261 0.6641 0.031 Uiso 1 1 calc R . . C31 C 0.0125(18) 0.6753(17) 0.6390(15) 0.026(5) Uiso 1 1 d . . . H31 H -0.0154 0.6062 0.6389 0.031 Uiso 1 1 calc R . . C32 C 0.1219(17) 0.7046(16) 0.6270(14) 0.020(5) Uiso 1 1 d . . . H32 H 0.1683 0.6560 0.6184 0.024 Uiso 1 1 calc R . . C33 C 0.1655(18) 0.8132(16) 0.6276(15) 0.023(5) Uiso 1 1 d . . . C34 C 0.2803(18) 0.8477(17) 0.6185(15) 0.024(5) Uiso 1 1 d . . . C35 C 0.4275(17) 0.9581(16) 0.5849(15) 0.021(5) Uiso 1 1 d . . . H35A H 0.4184 0.9507 0.5169 0.025 Uiso 1 1 calc R . . H35B H 0.4803 1.0287 0.6272 0.025 Uiso 1 1 calc R . . C36 C 0.4754(18) 0.8722(17) 0.6097(16) 0.026(5) Uiso 1 1 d . . . H36A H 0.4998 0.8307 0.5568 0.031 Uiso 1 1 calc R . . H36B H 0.5439 0.9020 0.6696 0.031 Uiso 1 1 calc R . . C37 C 0.3994(18) 0.7310(16) 0.6767(15) 0.024(5) Uiso 1 1 d . . . H37A H 0.3447 0.7264 0.7149 0.028 Uiso 1 1 calc R . . H37B H 0.4811 0.7603 0.7223 0.028 Uiso 1 1 calc R . . C38 C 0.3865(18) 0.6166(16) 0.6075(15) 0.023(5) Uiso 1 1 d . . . C39 C 0.3324(15) 0.5807(14) 0.5082(12) 0.008(4) Uiso 1 1 d . . . H39 H 0.3024 0.6259 0.4777 0.009 Uiso 1 1 calc R . . C40 C 0.3230(16) 0.4753(15) 0.4535(15) 0.017(5) Uiso 1 1 d . . . H40 H 0.2856 0.4479 0.3857 0.021 Uiso 1 1 calc R . . C41 C 0.3707(18) 0.4120(18) 0.5024(16) 0.028(6) Uiso 1 1 d . . . H41 H 0.3669 0.3415 0.4676 0.034 Uiso 1 1 calc R . . C42 C 0.4242(17) 0.4543(16) 0.6039(14) 0.019(5) Uiso 1 1 d . . . H42 H 0.4548 0.4109 0.6364 0.023 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 0.0171(13) 0.0191(14) 0.0223(15) 0.0075(12) -0.0010(11) 0.0010(11) Cu2 0.0168(13) 0.0234(15) 0.0181(15) 0.0112(12) 0.0041(11) 0.0020(11) Br1 0.0259(12) 0.0347(14) 0.0367(15) 0.0243(12) -0.0003(10) 0.0016(11) Br2 0.0182(11) 0.0187(12) 0.0343(14) 0.0086(10) 0.0061(9) 0.0036(9) Br3 0.0199(11) 0.0242(13) 0.0290(14) 0.0088(10) -0.0002(9) 0.0058(10) Br4 0.0188(11) 0.0296(13) 0.0265(13) 0.0129(10) 0.0030(9) -0.0007(10) Br5 0.0268(12) 0.0264(13) 0.0245(13) 0.0131(10) 0.0019(10) 0.0039(10) Br6 0.0277(12) 0.0349(14) 0.0338(15) 0.0210(11) 0.0170(10) 0.0125(11) _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 N3 2.024(15) . ? Cu1 Br3 2.363(3) . ? Cu1 Br1 2.394(3) . ? Cu1 Br2 2.402(3) . ? Cu2 N6 2.019(16) . ? Cu2 Br5 2.334(3) . ? Cu2 Br6 2.400(4) . ? Cu2 Br4 2.409(3) . ? N1 C13 1.33(2) . ? N1 C1 1.40(3) . ? N1 C14 1.46(2) . ? N2 C13 1.36(2) . ? N2 C16 1.46(2) . ? N2 C15 1.51(2) . ? N3 C17 1.29(2) . ? N3 C21 1.32(2) . ? N4 C34 1.35(3) . ? N4 C22 1.42(3) . ? N4 C35 1.51(2) . ? N5 C34 1.32(3) . ? N5 C36 1.47(2) . ? N5 C37 1.49(3) . ? N6 C42 1.33(3) . ? N6 C38 1.35(3) . ? C1 C2 1.39(3) . ? C1 C6 1.39(3) . ? C2 C3 1.36(3) . ? C3 C4 1.41(3) . ? C4 C5 1.33(3) . ? C5 C6 1.42(3) . ? C6 C7 1.44(3) . ? C7 C8 1.40(3) . ? C7 C12 1.43(3) . ? C8 C9 1.33(3) . ? C9 C10 1.41(3) . ? C10 C11 1.41(3) . ? C11 C12 1.39(3) . ? C12 C13 1.44(3) . ? C14 C15 1.51(3) . ? C16 C17 1.51(3) . ? C17 C18 1.41(3) . ? C18 C19 1.37(3) . ? C19 C20 1.38(3) . ? C20 C21 1.42(3) . ? C22 C23 1.37(3) . ? C22 C27 1.38(3) . ? C23 C24 1.36(3) . ? C24 C25 1.38(3) . ? C25 C26 1.40(3) . ? C26 C27 1.34(3) . ? C27 C28 1.51(3) . ? C28 C33 1.38(3) . ? C28 C29 1.41(3) . ? C29 C30 1.35(3) . ? C30 C31 1.39(3) . ? C31 C32 1.36(3) . ? C32 C33 1.46(3) . ? C33 C34 1.41(3) . ? C35 C36 1.48(3) . ? C37 C38 1.55(3) . ? C38 C39 1.36(3) . ? C39 C40 1.39(3) . ? C40 C41 1.38(3) . ? C41 C42 1.39(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 N3 Cu1 Br3 133.6(5) . . ? N3 Cu1 Br1 97.6(4) . . ? Br3 Cu1 Br1 101.69(12) . . ? N3 Cu1 Br2 97.5(5) . . ? Br3 Cu1 Br2 99.33(10) . . ? Br1 Cu1 Br2 133.01(15) . . ? N6 Cu2 Br5 132.7(5) . . ? N6 Cu2 Br6 97.1(5) . . ? Br5 Cu2 Br6 100.18(12) . . ? N6 Cu2 Br4 97.5(5) . . ? Br5 Cu2 Br4 101.28(12) . . ? Br6 Cu2 Br4 133.79(14) . . ? C13 N1 C1 124.6(16) . . ? C13 N1 C14 112.1(17) . . ? C1 N1 C14 123.2(15) . . ? C13 N2 C16 126.9(15) . . ? C13 N2 C15 108.3(15) . . ? C16 N2 C15 119.7(16) . . ? C17 N3 C21 120.2(17) . . ? C17 N3 Cu1 128.6(15) . . ? C21 N3 Cu1 111.2(12) . . ? C34 N4 C22 125.7(17) . . ? C34 N4 C35 109.1(17) . . ? C22 N4 C35 125.2(15) . . ? C34 N5 C36 112.8(17) . . ? C34 N5 C37 125.0(18) . . ? C36 N5 C37 117.3(16) . . ? C42 N6 C38 118.4(18) . . ? C42 N6 Cu2 114.5(14) . . ? C38 N6 Cu2 127.0(14) . . ? C2 C1 C6 123(2) . . ? C2 C1 N1 119.3(18) . . ? C6 C1 N1 117.4(17) . . ? C3 C2 C1 118(2) . . ? C2 C3 C4 121(2) . . ? C5 C4 C3 119(2) . . ? C4 C5 C6 124(2) . . ? C1 C6 C5 114.7(19) . . ? C1 C6 C7 121(2) . . ? C5 C6 C7 124.1(19) . . ? C8 C7 C12 116.8(18) . . ? C8 C7 C6 125(2) . . ? C12 C7 C6 118.0(17) . . ? C9 C8 C7 124(2) . . ? C8 C9 C10 121(2) . . ? C9 C10 C11 117(2) . . ? C12 C11 C10 122(2) . . ? C11 C12 C7 119.2(17) . . ? C11 C12 C13 121.6(19) . . ? C7 C12 C13 119.1(17) . . ? N1 C13 N2 111.1(16) . . ? N1 C13 C12 119.4(19) . . ? N2 C13 C12 129.5(18) . . ? N1 C14 C15 102.7(15) . . ? N2 C15 C14 103.7(16) . . ? N2 C16 C17 116.7(16) . . ? N3 C17 C18 123(2) . . ? N3 C17 C16 114.5(17) . . ? C18 C17 C16 122.1(18) . . ? C19 C18 C17 117(2) . . ? C18 C19 C20 120(2) . . ? C19 C20 C21 118(2) . . ? N3 C21 C20 121.4(19) . . ? C23 C22 C27 122(2) . . ? C23 C22 N4 120.3(19) . . ? C27 C22 N4 117.9(18) . . ? C24 C23 C22 119(2) . . ? C23 C24 C25 119(2) . . ? C24 C25 C26 121(2) . . ? C27 C26 C25 120(2) . . ? C26 C27 C22 119.3(19) . . ? C26 C27 C28 123.0(19) . . ? C22 C27 C28 118(2) . . ? C33 C28 C29 119.5(19) . . ? C33 C28 C27 120.0(19) . . ? C29 C28 C27 120(2) . . ? C30 C29 C28 121(2) . . ? C29 C30 C31 120(2) . . ? C32 C31 C30 122(2) . . ? C31 C32 C33 119(2) . . ? C28 C33 C34 120.8(19) . . ? C28 C33 C32 118.2(19) . . ? C34 C33 C32 121(2) . . ? N5 C34 N4 110.0(18) . . ? N5 C34 C33 132(2) . . ? N4 C34 C33 118(2) . . ? C36 C35 N4 103.8(15) . . ? N5 C36 C35 103.4(16) . . ? N5 C37 C38 113.0(17) . . ? N6 C38 C39 123.3(19) . . ? N6 C38 C37 113.1(17) . . ? C39 C38 C37 123.7(19) . . ? C38 C39 C40 118.7(19) . . ? C41 C40 C39 118.2(19) . . ? C40 C41 C42 120(2) . . ? N6 C42 C41 122(2) . . ? _diffrn_measured_fraction_theta_max 0.678 _diffrn_reflns_theta_full 23.00 _diffrn_measured_fraction_theta_full 0.678 _refine_diff_density_max 2.21 _refine_diff_density_min -0.94 _refine_diff_density_rms 0.26 # Attachment 'compound4.cif' data_ys02801 _database_code_depnum_ccdc_archive 'CCDC 678282' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C42 H36 Cu2 N24' _chemical_formula_weight 1004.03 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source Cu Cu 0.3201 1.2651 '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' 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 31.917(2) _cell_length_b 8.5868(5) _cell_length_c 15.9626(10) _cell_angle_alpha 90.00 _cell_angle_beta 107.844(2) _cell_angle_gamma 90.00 _cell_volume 4164.3(4) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 3049 _cell_measurement_theta_min 2.7 _cell_measurement_theta_max 23.7 _exptl_crystal_description block _exptl_crystal_colour green _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.601 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2056 _exptl_absorpt_coefficient_mu 1.089 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.7502 _exptl_absorpt_correction_T_max 0.8989 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _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 'Bruker Apex CCD' _diffrn_measurement_method '\w & \p' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% none _diffrn_reflns_number 18504 _diffrn_reflns_av_R_equivalents 0.0602 _diffrn_reflns_av_sigmaI/netI 0.0586 _diffrn_reflns_limit_h_min -38 _diffrn_reflns_limit_h_max 38 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.46 _diffrn_reflns_theta_max 25.78 _reflns_number_total 3981 _reflns_number_gt 2959 _reflns_threshold_expression >2sigma(I) _computing_data_collection Apex _computing_cell_refinement Apex _computing_data_reduction Apex _computing_structure_solution 'SHELXL-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics Mercury _computing_publication_material Wingx _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^)+(0.0327P)^2^+5.7482P] 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 none _refine_ls_number_reflns 3981 _refine_ls_number_parameters 307 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0611 _refine_ls_R_factor_gt 0.0381 _refine_ls_wR_factor_ref 0.0885 _refine_ls_wR_factor_gt 0.0782 _refine_ls_goodness_of_fit_ref 1.034 _refine_ls_restrained_S_all 1.034 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu Cu 0.041069(11) 0.10693(4) 0.21529(2) 0.01452(12) Uani 1 1 d . . . N1 N 0.18347(7) -0.4411(3) 0.47129(15) 0.0145(5) Uani 1 1 d . . . N2 N 0.12194(8) -0.3178(3) 0.40264(15) 0.0156(5) Uani 1 1 d . . . N3 N 0.04306(8) -0.1586(3) 0.20118(15) 0.0150(5) Uani 1 1 d . . . N4 N 0.02654(7) 0.1071(3) 0.33034(15) 0.0146(5) Uani 1 1 d . . . N5 N 0.04570(8) 0.1963(3) 0.38948(16) 0.0188(6) Uani 1 1 d . . . N6 N 0.06395(9) 0.2777(3) 0.44573(18) 0.0304(7) Uani 1 1 d . . . N7 N 0.04467(8) 0.1433(3) 0.09473(16) 0.0194(6) Uani 1 1 d . . . N8 N 0.07507(9) 0.0840(3) 0.07651(16) 0.0194(6) Uani 1 1 d . . . N9 N 0.10357(9) 0.0286(3) 0.05623(18) 0.0293(7) Uani 1 1 d . . . N10 N 0.10195(8) 0.1774(3) 0.27567(16) 0.0244(6) Uani 1 1 d . . . N11 N 0.12345(8) 0.2543(3) 0.24114(16) 0.0205(6) Uani 1 1 d . . . N12 N 0.14560(9) 0.3294(3) 0.21099(19) 0.0316(7) Uani 1 1 d . . . C1 C 0.22771(9) -0.4830(3) 0.49431(19) 0.0156(7) Uani 1 1 d . . . C2 C 0.24590(10) -0.5814(3) 0.56584(19) 0.0174(7) Uani 1 1 d . . . H2 H 0.2280 -0.6226 0.5983 0.021 Uiso 1 1 calc R . . C3 C 0.28992(10) -0.6187(3) 0.5892(2) 0.0209(7) Uani 1 1 d . . . H3 H 0.3024 -0.6857 0.6378 0.025 Uiso 1 1 calc R . . C4 C 0.31636(10) -0.5585(3) 0.5416(2) 0.0203(7) Uani 1 1 d . . . H4 H 0.3467 -0.5850 0.5577 0.024 Uiso 1 1 calc R . . C5 C 0.29846(9) -0.4609(3) 0.47140(19) 0.0178(7) Uani 1 1 d . . . H5 H 0.3169 -0.4195 0.4401 0.021 Uiso 1 1 calc R . . C6 C 0.25356(9) -0.4207(3) 0.44478(18) 0.0153(7) Uani 1 1 d . . . C7 C 0.23231(9) -0.3233(3) 0.36829(18) 0.0147(6) Uani 1 1 d . . . C8 C 0.25640(10) -0.2623(3) 0.31502(19) 0.0184(7) Uani 1 1 d . . . H8 H 0.2872 -0.2795 0.3308 0.022 Uiso 1 1 calc R . . C9 C 0.23572(10) -0.1781(3) 0.2406(2) 0.0221(7) Uani 1 1 d . . . H9 H 0.2526 -0.1356 0.2063 0.027 Uiso 1 1 calc R . . C10 C 0.19060(11) -0.1546(4) 0.2148(2) 0.0250(8) Uani 1 1 d . . . H10 H 0.1765 -0.1003 0.1619 0.030 Uiso 1 1 calc R . . C11 C 0.16629(10) -0.2101(3) 0.26625(19) 0.0207(7) Uani 1 1 d . . . H11 H 0.1354 -0.1935 0.2486 0.025 Uiso 1 1 calc R . . C12 C 0.18665(9) -0.2911(3) 0.34454(18) 0.0159(7) Uani 1 1 d . . . C13 C 0.16311(9) -0.3473(3) 0.40356(18) 0.0127(6) Uani 1 1 d . . . C14 C 0.15272(9) -0.4940(3) 0.51886(19) 0.0188(7) Uani 1 1 d . . . H14A H 0.1651 -0.4759 0.5830 0.023 Uiso 1 1 calc R . . H14B H 0.1455 -0.6058 0.5081 0.023 Uiso 1 1 calc R . . C15 C 0.11258(9) -0.3918(3) 0.47860(19) 0.0183(7) Uani 1 1 d . . . H15A H 0.0854 -0.4552 0.4592 0.022 Uiso 1 1 calc R . . H15B H 0.1093 -0.3126 0.5212 0.022 Uiso 1 1 calc R . . C16 C 0.09039(9) -0.2053(3) 0.34923(18) 0.0154(6) Uani 1 1 d . . . H16A H 0.1067 -0.1127 0.3392 0.018 Uiso 1 1 calc R . . H16B H 0.0706 -0.1709 0.3827 0.018 Uiso 1 1 calc R . . C17 C 0.06271(9) -0.2681(3) 0.26096(18) 0.0144(6) Uani 1 1 d . . . C18 C 0.05832(10) -0.4263(3) 0.2421(2) 0.0206(7) Uani 1 1 d . . . H18 H 0.0725 -0.5009 0.2855 0.025 Uiso 1 1 calc R . . C19 C 0.03292(10) -0.4740(4) 0.1587(2) 0.0232(7) Uani 1 1 d . . . H19 H 0.0296 -0.5815 0.1440 0.028 Uiso 1 1 calc R . . C20 C 0.01269(10) -0.3621(3) 0.09765(19) 0.0202(7) Uani 1 1 d . . . H20 H -0.0049 -0.3912 0.0402 0.024 Uiso 1 1 calc R . . C21 C 0.01844(9) -0.2069(3) 0.12135(19) 0.0165(7) Uani 1 1 d . . . H21 H 0.0043 -0.1307 0.0790 0.020 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 Cu 0.0117(2) 0.0148(2) 0.0171(2) 0.00150(16) 0.00434(15) 0.00072(15) N1 0.0133(13) 0.0140(13) 0.0175(13) 0.0017(11) 0.0066(11) 0.0007(10) N2 0.0119(13) 0.0151(13) 0.0188(13) 0.0032(11) 0.0033(11) 0.0023(11) N3 0.0124(13) 0.0152(13) 0.0172(13) 0.0003(11) 0.0043(11) 0.0012(10) N4 0.0151(13) 0.0132(12) 0.0146(13) -0.0033(11) 0.0035(10) -0.0020(11) N5 0.0151(14) 0.0197(14) 0.0232(15) 0.0046(13) 0.0083(12) 0.0023(12) N6 0.0283(17) 0.0325(16) 0.0272(16) -0.0114(14) 0.0040(13) -0.0092(14) N7 0.0169(14) 0.0222(15) 0.0189(13) 0.0032(11) 0.0055(11) 0.0028(11) N8 0.0210(15) 0.0182(14) 0.0195(14) 0.0023(11) 0.0069(12) -0.0035(12) N9 0.0270(16) 0.0299(16) 0.0363(17) 0.0001(14) 0.0178(14) 0.0042(14) N10 0.0141(14) 0.0366(16) 0.0217(14) 0.0104(13) 0.0042(12) -0.0030(13) N11 0.0133(14) 0.0238(15) 0.0224(14) 0.0012(12) 0.0023(12) 0.0023(12) N12 0.0212(16) 0.0357(17) 0.0391(17) 0.0096(14) 0.0112(14) -0.0038(14) C1 0.0145(16) 0.0125(15) 0.0184(16) -0.0046(13) 0.0029(13) 0.0014(13) C2 0.0189(17) 0.0152(16) 0.0180(16) -0.0010(13) 0.0056(13) -0.0023(13) C3 0.0219(17) 0.0174(16) 0.0201(16) 0.0007(14) 0.0015(14) 0.0028(14) C4 0.0135(16) 0.0207(17) 0.0241(17) -0.0072(14) 0.0020(14) 0.0016(13) C5 0.0168(17) 0.0182(16) 0.0185(16) -0.0073(14) 0.0057(13) -0.0039(13) C6 0.0172(16) 0.0147(16) 0.0134(15) -0.0035(12) 0.0038(13) 0.0004(13) C7 0.0187(16) 0.0093(14) 0.0167(15) -0.0066(12) 0.0063(13) -0.0025(12) C8 0.0182(17) 0.0163(16) 0.0223(17) -0.0034(13) 0.0086(14) -0.0018(13) C9 0.0292(19) 0.0186(16) 0.0238(17) -0.0017(14) 0.0158(15) -0.0052(14) C10 0.031(2) 0.0239(18) 0.0212(17) 0.0046(14) 0.0100(15) -0.0003(15) C11 0.0197(17) 0.0209(17) 0.0208(16) 0.0040(14) 0.0050(14) 0.0024(14) C12 0.0174(17) 0.0142(15) 0.0171(15) 0.0000(13) 0.0070(13) 0.0003(13) C13 0.0130(16) 0.0099(15) 0.0140(14) -0.0018(12) 0.0026(12) -0.0002(12) C14 0.0154(16) 0.0213(17) 0.0209(17) 0.0056(13) 0.0074(13) 0.0009(13) C15 0.0163(16) 0.0192(16) 0.0216(16) 0.0044(14) 0.0092(13) 0.0001(13) C16 0.0139(16) 0.0134(15) 0.0179(15) 0.0011(13) 0.0036(13) 0.0048(12) C17 0.0100(15) 0.0158(15) 0.0187(15) -0.0007(13) 0.0063(13) 0.0008(12) C18 0.0225(17) 0.0135(16) 0.0240(17) 0.0043(13) 0.0047(14) 0.0042(13) C19 0.0269(18) 0.0151(16) 0.0274(18) -0.0052(14) 0.0080(15) -0.0007(14) C20 0.0188(17) 0.0244(18) 0.0160(15) -0.0047(14) 0.0033(13) -0.0037(14) C21 0.0136(16) 0.0182(16) 0.0171(15) 0.0003(13) 0.0037(13) 0.0003(13) _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 Cu N10 1.981(3) . ? Cu N7 1.987(2) . ? Cu N4 2.027(2) . ? Cu N4 2.055(2) 2 ? Cu N3 2.294(2) . ? N1 C13 1.345(3) . ? N1 C1 1.393(4) . ? N1 C14 1.484(3) . ? N2 C13 1.334(3) . ? N2 C16 1.465(3) . ? N2 C15 1.479(3) . ? N3 C21 1.342(4) . ? N3 C17 1.350(4) . ? N4 N5 1.224(3) . ? N4 Cu 2.055(2) 2 ? N5 N6 1.146(3) . ? N7 N8 1.207(3) . ? N8 N9 1.157(3) . ? N10 N11 1.201(3) . ? N11 N12 1.164(3) . ? C1 C2 1.396(4) . ? C1 C6 1.411(4) . ? C2 C3 1.376(4) . ? C3 C4 1.396(4) . ? C4 C5 1.376(4) . ? C5 C6 1.407(4) . ? C6 C7 1.464(4) . ? C7 C8 1.410(4) . ? C7 C12 1.416(4) . ? C8 C9 1.375(4) . ? C9 C10 1.386(4) . ? C10 C11 1.376(4) . ? C11 C12 1.403(4) . ? C12 C13 1.456(4) . ? C14 C15 1.523(4) . ? C16 C17 1.514(4) . ? C17 C18 1.389(4) . ? C18 C19 1.392(4) . ? C19 C20 1.380(4) . ? C20 C21 1.382(4) . ? 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 N10 Cu N7 94.82(10) . . ? N10 Cu N4 91.23(10) . . ? N7 Cu N4 166.98(10) . . ? N10 Cu N4 159.90(10) . 2 ? N7 Cu N4 91.30(10) . 2 ? N4 Cu N4 79.30(10) . 2 ? N10 Cu N3 107.40(10) . . ? N7 Cu N3 92.83(9) . . ? N4 Cu N3 96.35(9) . . ? N4 Cu N3 91.36(9) 2 . ? C13 N1 C1 124.6(2) . . ? C13 N1 C14 111.2(2) . . ? C1 N1 C14 124.2(2) . . ? C13 N2 C16 129.1(2) . . ? C13 N2 C15 110.8(2) . . ? C16 N2 C15 119.0(2) . . ? C21 N3 C17 117.8(2) . . ? C21 N3 Cu 112.03(18) . . ? C17 N3 Cu 130.10(19) . . ? N5 N4 Cu 120.01(19) . . ? N5 N4 Cu 119.74(19) . 2 ? Cu N4 Cu 100.70(10) . 2 ? N6 N5 N4 178.8(3) . . ? N8 N7 Cu 117.15(19) . . ? N9 N8 N7 177.8(3) . . ? N11 N10 Cu 123.9(2) . . ? N12 N11 N10 177.2(3) . . ? N1 C1 C2 120.4(3) . . ? N1 C1 C6 118.3(3) . . ? C2 C1 C6 121.3(3) . . ? C3 C2 C1 119.8(3) . . ? C2 C3 C4 120.3(3) . . ? C5 C4 C3 120.0(3) . . ? C4 C5 C6 121.7(3) . . ? C5 C6 C1 117.0(3) . . ? C5 C6 C7 124.1(3) . . ? C1 C6 C7 118.9(3) . . ? C8 C7 C12 118.2(3) . . ? C8 C7 C6 121.1(3) . . ? C12 C7 C6 120.7(3) . . ? C9 C8 C7 120.7(3) . . ? C8 C9 C10 120.9(3) . . ? C11 C10 C9 119.8(3) . . ? C10 C11 C12 120.7(3) . . ? C11 C12 C7 119.5(3) . . ? C11 C12 C13 123.4(3) . . ? C7 C12 C13 117.1(3) . . ? N2 C13 N1 110.8(2) . . ? N2 C13 C12 129.2(3) . . ? N1 C13 C12 120.1(2) . . ? N1 C14 C15 102.1(2) . . ? N2 C15 C14 103.8(2) . . ? N2 C16 C17 114.1(2) . . ? N3 C17 C18 122.3(3) . . ? N3 C17 C16 115.0(2) . . ? C18 C17 C16 122.8(3) . . ? C17 C18 C19 119.1(3) . . ? C20 C19 C18 118.7(3) . . ? C19 C20 C21 118.9(3) . . ? N3 C21 C20 123.3(3) . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 25.78 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.63 _refine_diff_density_min -0.44 _refine_diff_density_rms 0.08 # Attachment 'compound5.cif' data_ys05701 _database_code_depnum_ccdc_archive 'CCDC 678283' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '(C48 H42 Cu2 N10 O2 S4), (C H4 O)' _chemical_formula_sum 'C49 H46 Cu2 N10 O3 S4' _chemical_formula_weight 1078.28 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source Cu Cu 0.3201 1.2651 '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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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' _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 9.2344(7) _cell_length_b 11.5240(9) _cell_length_c 12.4542(9) _cell_angle_alpha 65.526(3) _cell_angle_beta 88.615(3) _cell_angle_gamma 80.281(3) _cell_volume 1187.40(16) _cell_formula_units_Z 1 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 3830 _cell_measurement_theta_min 2.8 _cell_measurement_theta_max 24 _exptl_crystal_description block _exptl_crystal_colour green _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.508 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 556 _exptl_absorpt_coefficient_mu 1.126 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.7660 _exptl_absorpt_correction_T_max 0.8767 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _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 'Bruker Apex CCD' _diffrn_measurement_method '\w & \p scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% none _diffrn_reflns_number 18035 _diffrn_reflns_av_R_equivalents 0.0501 _diffrn_reflns_av_sigmaI/netI 0.0503 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 1.80 _diffrn_reflns_theta_max 24.20 _reflns_number_total 3771 _reflns_number_gt 2813 _reflns_threshold_expression >2sigma(I) _computing_data_collection Apex _computing_cell_refinement Apex _computing_data_reduction Apex _computing_structure_solution 'SHELXS-97 (sHELDRICK, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics Mercury _computing_publication_material Wingx _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^)+(0.0508P)^2^+2.3353P] 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 none _refine_ls_number_reflns 3771 _refine_ls_number_parameters 308 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0720 _refine_ls_R_factor_gt 0.0455 _refine_ls_wR_factor_ref 0.1210 _refine_ls_wR_factor_gt 0.1056 _refine_ls_goodness_of_fit_ref 1.030 _refine_ls_restrained_S_all 1.030 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu Cu 0.47309(6) 0.93199(5) 0.92342(5) 0.03164(19) Uani 1 1 d . . . N1 N 0.7641(4) 0.3674(3) 1.3554(3) 0.0275(8) Uani 1 1 d . . . N2 N 0.6536(4) 0.5299(3) 1.1972(3) 0.0258(8) Uani 1 1 d . . . N3 N 0.6135(4) 0.7919(3) 0.8953(3) 0.0258(8) Uani 1 1 d . . . N4 N 0.3063(4) 0.8601(4) 0.8992(4) 0.0416(10) Uani 1 1 d . . . N5 N 0.4797(5) 1.0901(5) 0.7433(5) 0.086(2) Uani 1 1 d . . . S1 S 0.07566(13) 0.75591(11) 0.85138(11) 0.0362(3) Uani 1 1 d . . . S2 S 0.47672(12) 1.34995(11) 0.59952(11) 0.0339(3) Uani 1 1 d . . . O O 0.3667(3) 1.0327(3) 1.0022(3) 0.0379(8) Uani 1 1 d . . . O1 O 0.4295(5) 0.0213(5) 0.5121(4) 0.0661(14) Uani 0.50 1 d P . . C C 0.4295(5) 0.0213(5) 0.5121(4) 0.0661(14) Uani 0.50 1 d P . . C1 C 0.8724(5) 0.2911(4) 1.4452(4) 0.0318(11) Uani 1 1 d . . . C2 C 0.8540(6) 0.1674(5) 1.5262(4) 0.0437(13) Uani 1 1 d . . . H2 H 0.7683 0.1344 1.5209 0.052 Uiso 1 1 calc R . . C3 C 0.9616(6) 0.0944(5) 1.6136(4) 0.0539(16) Uani 1 1 d . . . H3 H 0.9502 0.0101 1.6686 0.065 Uiso 1 1 calc R . . C4 C 1.0875(6) 0.1432(6) 1.6221(4) 0.0502(15) Uani 1 1 d . . . H4 H 1.1612 0.0922 1.6829 0.060 Uiso 1 1 calc R . . C5 C 1.1051(5) 0.2651(5) 1.5426(4) 0.0404(13) Uani 1 1 d . . . H5 H 1.1911 0.2973 1.5490 0.048 Uiso 1 1 calc R . . C6 C 0.9971(5) 0.3428(4) 1.4517(4) 0.0294(11) Uani 1 1 d . . . C7 C 1.0111(5) 0.4723(4) 1.3633(4) 0.0284(10) Uani 1 1 d . . . C8 C 1.1351(5) 0.5289(5) 1.3635(4) 0.0336(11) Uani 1 1 d . . . H8 H 1.2088 0.4847 1.4255 0.040 Uiso 1 1 calc R . . C9 C 1.1516(5) 0.6463(5) 1.2761(4) 0.0371(12) Uani 1 1 d . . . H9 H 1.2359 0.6826 1.2784 0.044 Uiso 1 1 calc R . . C10 C 1.0451(5) 0.7126(5) 1.1841(4) 0.0367(12) Uani 1 1 d . . . H10 H 1.0584 0.7927 1.1225 0.044 Uiso 1 1 calc R . . C11 C 0.9213(5) 0.6626(5) 1.1821(4) 0.0331(11) Uani 1 1 d . . . H11 H 0.8489 0.7089 1.1193 0.040 Uiso 1 1 calc R . . C12 C 0.9000(5) 0.5439(4) 1.2714(4) 0.0266(10) Uani 1 1 d . . . C13 C 0.7719(4) 0.4855(4) 1.2719(4) 0.0252(10) Uani 1 1 d . . . C14 C 0.6331(5) 0.3192(4) 1.3354(4) 0.0337(11) Uani 1 1 d . . . H14A H 0.5734 0.2931 1.4060 0.040 Uiso 1 1 calc R . . H14B H 0.6611 0.2449 1.3140 0.040 Uiso 1 1 calc R . . C15 C 0.5508(5) 0.4374(4) 1.2323(4) 0.0322(11) Uani 1 1 d . . . H15A H 0.5283 0.4152 1.1665 0.039 Uiso 1 1 calc R . . H15B H 0.4578 0.4732 1.2574 0.039 Uiso 1 1 calc R . . C16 C 0.6029(5) 0.6588(4) 1.1048(3) 0.0244(10) Uani 1 1 d . . . H16A H 0.6366 0.7237 1.1265 0.029 Uiso 1 1 calc R . . H16B H 0.4940 0.6764 1.0995 0.029 Uiso 1 1 calc R . . C17 C 0.6584(4) 0.6740(4) 0.9852(3) 0.0217(9) Uani 1 1 d . . . C18 C 0.7493(4) 0.5761(4) 0.9671(4) 0.0280(10) Uani 1 1 d . . . H18 H 0.7803 0.4945 1.0312 0.034 Uiso 1 1 calc R . . C19 C 0.7949(5) 0.5985(5) 0.8543(4) 0.0365(12) Uani 1 1 d . . . H19 H 0.8575 0.5324 0.8403 0.044 Uiso 1 1 calc R . . C20 C 0.7482(5) 0.7181(5) 0.7626(4) 0.0389(13) Uani 1 1 d . . . H20 H 0.7770 0.7353 0.6845 0.047 Uiso 1 1 calc R . . C21 C 0.6594(5) 0.8115(5) 0.7866(4) 0.0358(12) Uani 1 1 d . . . H21 H 0.6288 0.8941 0.7236 0.043 Uiso 1 1 calc R . . C22 C 0.2110(5) 0.8161(4) 0.8792(4) 0.0284(10) Uani 1 1 d . . . C23 C 0.4785(5) 1.1977(5) 0.6840(4) 0.0356(12) Uani 1 1 d . . . C24 C 0.2318(5) 1.0079(5) 1.0567(5) 0.0478(14) Uani 1 1 d . . . H24A H 0.1629 1.0017 1.0014 0.072 Uiso 1 1 calc R . . H24B H 0.1899 1.0786 1.0786 0.072 Uiso 1 1 calc R . . H24C H 0.2494 0.9261 1.1277 0.072 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 Cu 0.0206(3) 0.0233(3) 0.0425(4) -0.0058(3) -0.0022(2) -0.0024(2) N1 0.0243(19) 0.029(2) 0.022(2) -0.0027(17) -0.0011(16) -0.0058(16) N2 0.0250(19) 0.024(2) 0.024(2) -0.0053(16) -0.0032(16) -0.0061(16) N3 0.0248(19) 0.030(2) 0.0210(19) -0.0085(17) -0.0009(15) -0.0063(16) N4 0.026(2) 0.042(3) 0.055(3) -0.020(2) -0.003(2) -0.0035(19) N5 0.045(3) 0.048(3) 0.099(4) 0.034(3) 0.001(3) 0.001(2) S1 0.0310(6) 0.0314(7) 0.0482(8) -0.0200(6) -0.0125(5) 0.0005(5) S2 0.0286(6) 0.0284(7) 0.0410(7) -0.0117(6) -0.0027(5) -0.0019(5) O 0.0140(16) 0.0251(17) 0.074(2) -0.0194(17) 0.0057(15) -0.0065(13) O1 0.062(3) 0.077(4) 0.056(3) -0.029(3) -0.014(3) 0.000(3) C 0.062(3) 0.077(4) 0.056(3) -0.029(3) -0.014(3) 0.000(3) C1 0.027(2) 0.038(3) 0.023(2) -0.008(2) 0.0006(19) 0.002(2) C2 0.039(3) 0.041(3) 0.035(3) -0.001(2) 0.004(2) -0.005(2) C3 0.050(4) 0.047(3) 0.031(3) 0.010(3) 0.004(3) 0.010(3) C4 0.042(3) 0.062(4) 0.025(3) -0.008(3) -0.003(2) 0.021(3) C5 0.030(3) 0.061(4) 0.027(3) -0.021(3) -0.006(2) 0.011(2) C6 0.025(2) 0.043(3) 0.016(2) -0.012(2) 0.0001(18) 0.003(2) C7 0.023(2) 0.044(3) 0.023(2) -0.020(2) 0.0030(19) -0.003(2) C8 0.025(2) 0.052(3) 0.030(3) -0.025(3) 0.000(2) -0.001(2) C9 0.023(2) 0.058(3) 0.047(3) -0.036(3) 0.007(2) -0.016(2) C10 0.039(3) 0.046(3) 0.034(3) -0.021(2) 0.007(2) -0.019(2) C11 0.035(3) 0.041(3) 0.028(3) -0.015(2) -0.002(2) -0.015(2) C12 0.026(2) 0.035(3) 0.022(2) -0.015(2) 0.0018(19) -0.007(2) C13 0.025(2) 0.028(3) 0.021(2) -0.009(2) 0.0006(19) -0.0052(19) C14 0.029(3) 0.029(3) 0.036(3) -0.005(2) -0.002(2) -0.011(2) C15 0.027(2) 0.032(3) 0.036(3) -0.010(2) -0.002(2) -0.009(2) C16 0.024(2) 0.025(2) 0.024(2) -0.011(2) 0.0011(18) -0.0045(18) C17 0.018(2) 0.027(2) 0.023(2) -0.012(2) -0.0033(18) -0.0075(18) C18 0.020(2) 0.030(3) 0.040(3) -0.021(2) 0.001(2) -0.0063(19) C19 0.029(3) 0.052(3) 0.049(3) -0.038(3) 0.014(2) -0.018(2) C20 0.041(3) 0.063(4) 0.031(3) -0.031(3) 0.014(2) -0.030(3) C21 0.035(3) 0.048(3) 0.024(3) -0.011(2) 0.000(2) -0.018(2) C22 0.025(3) 0.026(3) 0.032(3) -0.013(2) 0.000(2) 0.005(2) C23 0.019(2) 0.041(3) 0.031(3) -0.002(2) 0.001(2) 0.000(2) C24 0.024(3) 0.034(3) 0.090(4) -0.029(3) 0.008(3) -0.010(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu O 1.946(3) . ? Cu O 1.948(3) 2_677 ? Cu N4 1.951(4) . ? Cu N3 2.038(3) . ? Cu N5 2.236(5) . ? Cu Cu 3.0213(12) 2_677 ? N1 C13 1.340(5) . ? N1 C1 1.402(5) . ? N1 C14 1.480(5) . ? N2 C13 1.336(5) . ? N2 C16 1.458(5) . ? N2 C15 1.471(5) . ? N3 C21 1.346(5) . ? N3 C17 1.357(5) . ? N4 C22 1.167(6) . ? N5 C23 1.149(6) . ? S1 C22 1.636(5) . ? S2 C23 1.627(5) . ? O C24 1.419(5) . ? O Cu 1.948(3) 2_677 ? O1 C 1.383(9) 2_656 ? O1 O1 1.383(9) 2_656 ? C1 C2 1.400(7) . ? C1 C6 1.401(6) . ? C2 C3 1.375(7) . ? C3 C4 1.399(8) . ? C4 C5 1.377(8) . ? C5 C6 1.411(6) . ? C6 C7 1.467(6) . ? C7 C8 1.410(6) . ? C7 C12 1.426(6) . ? C8 C9 1.371(7) . ? C9 C10 1.393(7) . ? C10 C11 1.370(6) . ? C11 C12 1.402(6) . ? C12 C13 1.455(6) . ? C14 C15 1.527(6) . ? C16 C17 1.512(5) . ? C17 C18 1.382(6) . ? C18 C19 1.387(6) . ? C19 C20 1.382(7) . ? C20 C21 1.370(7) . ? 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 O Cu O 78.22(13) . 2_677 ? O Cu N4 96.33(15) . . ? O Cu N4 162.30(16) 2_677 . ? O Cu N3 161.29(14) . . ? O Cu N3 90.56(13) 2_677 . ? N4 Cu N3 89.87(15) . . ? O Cu N5 99.54(19) . . ? O Cu N5 97.18(19) 2_677 . ? N4 Cu N5 100.3(2) . . ? N3 Cu N5 96.66(19) . . ? O Cu Cu 39.13(9) . 2_677 ? O Cu Cu 39.10(9) 2_677 2_677 ? N4 Cu Cu 133.25(12) . 2_677 ? N3 Cu Cu 128.06(10) . 2_677 ? N5 Cu Cu 100.80(19) . 2_677 ? C13 N1 C1 125.2(4) . . ? C13 N1 C14 111.9(3) . . ? C1 N1 C14 122.7(4) . . ? C13 N2 C16 130.0(4) . . ? C13 N2 C15 111.2(3) . . ? C16 N2 C15 117.7(3) . . ? C21 N3 C17 118.2(4) . . ? C21 N3 Cu 121.1(3) . . ? C17 N3 Cu 120.6(3) . . ? C22 N4 Cu 175.9(4) . . ? C23 N5 Cu 149.5(6) . . ? C24 O Cu 123.5(3) . . ? C24 O Cu 122.6(3) . 2_677 ? Cu O Cu 101.78(13) . 2_677 ? C O1 O1 0.0(5) 2_656 2_656 ? C2 C1 C6 121.6(4) . . ? C2 C1 N1 120.2(4) . . ? C6 C1 N1 118.2(4) . . ? C3 C2 C1 119.3(5) . . ? C2 C3 C4 120.5(5) . . ? C5 C4 C3 120.2(5) . . ? C4 C5 C6 120.9(5) . . ? C1 C6 C5 117.6(4) . . ? C1 C6 C7 119.1(4) . . ? C5 C6 C7 123.3(4) . . ? C8 C7 C12 117.6(4) . . ? C8 C7 C6 122.0(4) . . ? C12 C7 C6 120.4(4) . . ? C9 C8 C7 121.5(4) . . ? C8 C9 C10 120.2(4) . . ? C11 C10 C9 120.2(5) . . ? C10 C11 C12 120.9(4) . . ? C11 C12 C7 119.5(4) . . ? C11 C12 C13 122.9(4) . . ? C7 C12 C13 117.5(4) . . ? N2 C13 N1 110.3(4) . . ? N2 C13 C12 130.0(4) . . ? N1 C13 C12 119.6(4) . . ? N1 C14 C15 102.0(3) . . ? N2 C15 C14 103.9(3) . . ? N2 C16 C17 112.8(3) . . ? N3 C17 C18 121.5(4) . . ? N3 C17 C16 115.4(3) . . ? C18 C17 C16 123.1(4) . . ? C17 C18 C19 119.2(4) . . ? C20 C19 C18 119.2(4) . . ? C21 C20 C19 118.7(4) . . ? N3 C21 C20 123.1(4) . . ? N4 C22 S1 179.2(4) . . ? N5 C23 S2 179.8(6) . . ? _diffrn_measured_fraction_theta_max 0.986 _diffrn_reflns_theta_full 24.20 _diffrn_measured_fraction_theta_full 0.986 _refine_diff_density_max 1.54 _refine_diff_density_min -0.49 _refine_diff_density_rms 0.08 # Attachment 'compound6.cif' data_pk355c _database_code_depnum_ccdc_archive 'CCDC 678284' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C42 H38 Br4 Cu N6 O' _chemical_formula_weight 1025.96 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 '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' 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 13.1236(6) _cell_length_b 22.2503(11) _cell_length_c 13.7765(10) _cell_angle_alpha 90.00 _cell_angle_beta 101.917(2) _cell_angle_gamma 90.00 _cell_volume 3936.1(4) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 2417 _cell_measurement_theta_min 2.4 _cell_measurement_theta_max 22.5 _exptl_crystal_description block _exptl_crystal_colour green _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.731 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2036 _exptl_absorpt_coefficient_mu 4.658 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.4560 _exptl_absorpt_correction_T_max 0.6530 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _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 'Bruker Apex CCD' _diffrn_measurement_method '\w & \p scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% none _diffrn_reflns_number 13804 _diffrn_reflns_av_R_equivalents 0.0561 _diffrn_reflns_av_sigmaI/netI 0.0494 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 1.83 _diffrn_reflns_theta_max 23.29 _reflns_number_total 2829 _reflns_number_gt 2157 _reflns_threshold_expression >2sigma(I) _computing_data_collection Apex _computing_cell_refinement Apex _computing_data_reduction Apex _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics Mercury _computing_publication_material Wingx _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^)+(0.0649P)^2^+76.4964P] 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 none _refine_ls_number_reflns 2829 _refine_ls_number_parameters 254 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0776 _refine_ls_R_factor_gt 0.0553 _refine_ls_wR_factor_ref 0.1513 _refine_ls_wR_factor_gt 0.1384 _refine_ls_goodness_of_fit_ref 1.056 _refine_ls_restrained_S_all 1.056 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu Cu 0.0000 0.87570(6) 0.7500 0.0207(4) Uani 1 2 d S . . Br1 Br 0.0000 0.98756(5) 0.7500 0.0284(4) Uani 1 2 d S . . Br2 Br -0.13610(6) 0.80298(4) 0.65296(7) 0.0262(3) Uani 1 1 d . . . Br3 Br 0.42696(15) 0.78222(10) 0.64975(18) 0.0469(6) Uani 0.50 1 d P . . O1 O 0.1375(13) 0.7670(7) 0.141(3) 0.197(19) Uani 0.50 1 d P . . N1 N 0.4670(6) 0.8741(3) 0.3814(5) 0.0252(17) Uani 1 1 d . . . N2 N 0.2988(5) 0.8645(3) 0.3783(5) 0.0238(17) Uani 1 1 d . . . N3 N 0.0660(5) 0.8786(3) 0.6308(5) 0.0213(16) Uani 1 1 d . . . C1 C 0.5610(6) 0.9013(4) 0.3778(6) 0.026(2) Uani 1 1 d . . . C2 C 0.6504(7) 0.8666(4) 0.3793(7) 0.033(2) Uani 1 1 d . . . H2 H 0.6470 0.8241 0.3844 0.040 Uiso 1 1 calc R . . C3 C 0.7423(7) 0.8935(5) 0.3736(7) 0.033(2) Uani 1 1 d . . . H3 H 0.8026 0.8697 0.3751 0.040 Uiso 1 1 calc R . . C4 C 0.7481(7) 0.9551(5) 0.3656(7) 0.035(2) Uani 1 1 d . . . H4 H 0.8121 0.9736 0.3610 0.043 Uiso 1 1 calc R . . C5 C 0.6605(7) 0.9899(5) 0.3644(6) 0.031(2) Uani 1 1 d . . . H5 H 0.6651 1.0323 0.3593 0.037 Uiso 1 1 calc R . . C6 C 0.5641(7) 0.9633(4) 0.3706(6) 0.023(2) Uani 1 1 d . . . C7 C 0.4701(7) 0.9975(4) 0.3729(6) 0.024(2) Uani 1 1 d . . . C8 C 0.4687(7) 1.0610(4) 0.3678(6) 0.025(2) Uani 1 1 d . . . H8 H 0.5301 1.0821 0.3621 0.030 Uiso 1 1 calc R . . C9 C 0.3792(7) 1.0926(4) 0.3710(6) 0.030(2) Uani 1 1 d . . . H9 H 0.3788 1.1351 0.3642 0.035 Uiso 1 1 calc R . . C10 C 0.2906(7) 1.0636(4) 0.3839(6) 0.027(2) Uani 1 1 d . . . H10 H 0.2299 1.0860 0.3879 0.033 Uiso 1 1 calc R . . C11 C 0.2901(6) 1.0021(4) 0.3909(6) 0.025(2) Uani 1 1 d . . . H11 H 0.2295 0.9823 0.4024 0.029 Uiso 1 1 calc R . . C12 C 0.3768(7) 0.9682(4) 0.3815(6) 0.0221(19) Uani 1 1 d . . . C13 C 0.3768(6) 0.9035(4) 0.3808(6) 0.0205(19) Uani 1 1 d . . . C14 C 0.4516(7) 0.8086(4) 0.3848(8) 0.035(2) Uani 1 1 d . . . H14A H 0.4898 0.7915 0.4483 0.043 Uiso 1 1 calc R . . H14B H 0.4749 0.7883 0.3292 0.043 Uiso 1 1 calc R . . C15 C 0.3353(7) 0.8026(4) 0.3752(8) 0.033(2) Uani 1 1 d . . . H15A H 0.3029 0.7830 0.3118 0.040 Uiso 1 1 calc R . . H15B H 0.3189 0.7788 0.4308 0.040 Uiso 1 1 calc R . . C16 C 0.1878(7) 0.8753(4) 0.3632(6) 0.025(2) Uani 1 1 d . . . H16A H 0.1505 0.8423 0.3225 0.030 Uiso 1 1 calc R . . H16B H 0.1710 0.9132 0.3257 0.030 Uiso 1 1 calc R . . C17 C 0.1489(6) 0.8795(4) 0.4602(6) 0.023(2) Uani 1 1 d . . . C18 C 0.2083(6) 0.8640(4) 0.5497(6) 0.026(2) Uani 1 1 d . . . H18 H 0.2791 0.8530 0.5548 0.031 Uiso 1 1 calc R . . C19 C 0.1647(7) 0.8644(4) 0.6343(6) 0.024(2) Uani 1 1 d . . . H19 H 0.2075 0.8541 0.6965 0.029 Uiso 1 1 calc R . . C20 C 0.0103(7) 0.8969(5) 0.5450(7) 0.038(2) Uani 1 1 d . . . H20 H -0.0589 0.9103 0.5430 0.045 Uiso 1 1 calc R . . C21 C 0.0467(7) 0.8975(5) 0.4584(7) 0.039(3) Uani 1 1 d . . . H21 H 0.0028 0.9101 0.3980 0.047 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu 0.0259(8) 0.0191(8) 0.0223(8) 0.000 0.0173(6) 0.000 Br1 0.0405(8) 0.0201(7) 0.0280(7) 0.000 0.0148(6) 0.000 Br2 0.0269(5) 0.0204(5) 0.0317(5) -0.0041(4) 0.0072(4) 0.0036(4) Br3 0.0319(11) 0.0410(12) 0.0706(16) 0.0252(11) 0.0173(10) 0.0024(9) O1 0.042(10) 0.011(9) 0.57(6) 0.026(18) 0.13(2) 0.013(8) N1 0.036(4) 0.023(4) 0.020(4) -0.005(3) 0.014(3) 0.009(3) N2 0.029(4) 0.023(4) 0.024(4) 0.002(3) 0.018(3) 0.006(3) N3 0.028(4) 0.020(4) 0.019(4) -0.002(3) 0.014(3) 0.002(3) C1 0.025(5) 0.032(5) 0.022(5) -0.001(4) 0.010(4) 0.002(4) C2 0.038(6) 0.038(6) 0.023(5) -0.011(4) 0.005(4) 0.011(5) C3 0.023(5) 0.046(7) 0.031(6) -0.013(5) 0.008(4) 0.001(5) C4 0.024(5) 0.061(7) 0.022(5) -0.005(5) 0.008(4) -0.002(5) C5 0.039(6) 0.042(6) 0.015(5) -0.003(4) 0.010(4) 0.001(5) C6 0.031(5) 0.035(6) 0.005(4) 0.002(4) 0.005(4) 0.003(4) C7 0.031(5) 0.032(5) 0.011(4) 0.004(4) 0.005(4) 0.008(4) C8 0.037(5) 0.023(5) 0.016(5) 0.001(4) 0.008(4) -0.002(4) C9 0.043(6) 0.021(5) 0.025(5) 0.006(4) 0.008(4) 0.004(4) C10 0.037(5) 0.025(5) 0.020(5) 0.005(4) 0.005(4) 0.014(4) C11 0.021(4) 0.035(6) 0.019(5) 0.003(4) 0.007(4) 0.008(4) C12 0.033(5) 0.023(5) 0.010(4) -0.002(3) 0.006(4) 0.007(4) C13 0.032(5) 0.024(5) 0.008(4) 0.001(3) 0.009(4) 0.005(4) C14 0.041(6) 0.028(5) 0.042(6) -0.002(4) 0.019(5) 0.011(4) C15 0.039(5) 0.020(5) 0.047(6) -0.005(4) 0.024(5) 0.007(4) C16 0.032(5) 0.030(5) 0.017(5) 0.003(4) 0.012(4) 0.006(4) C17 0.029(5) 0.022(5) 0.025(5) -0.003(4) 0.019(4) -0.001(4) C18 0.018(4) 0.033(5) 0.031(6) 0.000(4) 0.014(4) 0.002(4) C19 0.030(5) 0.021(5) 0.023(5) -0.003(4) 0.013(4) -0.005(4) C20 0.033(5) 0.049(6) 0.035(6) 0.018(5) 0.016(5) 0.018(5) C21 0.040(6) 0.054(7) 0.030(6) 0.020(5) 0.019(5) 0.019(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 Cu N3 2.010(6) 2_556 ? Cu N3 2.010(6) . ? Cu Br1 2.4888(18) . ? Cu Br2 2.5709(12) . ? Cu Br2 2.5709(12) 2_556 ? N1 C13 1.350(10) . ? N1 C1 1.384(11) . ? N1 C14 1.474(11) . ? N2 C13 1.336(11) . ? N2 C16 1.447(11) . ? N2 C15 1.463(11) . ? N3 C20 1.319(11) . ? N3 C19 1.325(11) . ? C1 C6 1.383(12) . ? C1 C2 1.401(12) . ? C2 C3 1.363(13) . ? C3 C4 1.378(14) . ? C4 C5 1.382(13) . ? C5 C6 1.414(12) . ? C6 C7 1.456(12) . ? C7 C12 1.414(12) . ? C7 C8 1.414(12) . ? C8 C9 1.377(12) . ? C9 C10 1.374(13) . ? C10 C11 1.372(12) . ? C11 C12 1.393(11) . ? C12 C13 1.441(12) . ? C14 C15 1.511(13) . ? C16 C17 1.529(11) . ? C17 C18 1.360(12) . ? C17 C21 1.395(12) . ? C18 C19 1.400(11) . ? C20 C21 1.375(13) . ? 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 N3 Cu N3 176.3(4) 2_556 . ? N3 Cu Br1 88.13(19) 2_556 . ? N3 Cu Br1 88.13(19) . . ? N3 Cu Br2 94.3(2) 2_556 . ? N3 Cu Br2 88.1(2) . . ? Br1 Cu Br2 129.00(3) . . ? N3 Cu Br2 88.1(2) 2_556 2_556 ? N3 Cu Br2 94.3(2) . 2_556 ? Br1 Cu Br2 129.00(3) . 2_556 ? Br2 Cu Br2 101.99(6) . 2_556 ? C13 N1 C1 125.1(7) . . ? C13 N1 C14 110.7(7) . . ? C1 N1 C14 124.2(7) . . ? C13 N2 C16 129.7(7) . . ? C13 N2 C15 111.0(7) . . ? C16 N2 C15 118.5(7) . . ? C20 N3 C19 117.7(7) . . ? C20 N3 Cu 119.3(6) . . ? C19 N3 Cu 123.0(6) . . ? C6 C1 N1 118.6(8) . . ? C6 C1 C2 120.8(8) . . ? N1 C1 C2 120.6(8) . . ? C3 C2 C1 120.4(9) . . ? C2 C3 C4 120.4(9) . . ? C3 C4 C5 119.8(9) . . ? C4 C5 C6 121.1(9) . . ? C1 C6 C5 117.5(8) . . ? C1 C6 C7 118.8(8) . . ? C5 C6 C7 123.7(8) . . ? C12 C7 C8 117.5(8) . . ? C12 C7 C6 120.9(8) . . ? C8 C7 C6 121.6(8) . . ? C9 C8 C7 120.7(8) . . ? C10 C9 C8 121.0(8) . . ? C11 C10 C9 119.6(8) . . ? C10 C11 C12 121.1(8) . . ? C11 C12 C7 119.8(8) . . ? C11 C12 C13 122.9(8) . . ? C7 C12 C13 117.3(7) . . ? N2 C13 N1 110.6(7) . . ? N2 C13 C12 130.4(8) . . ? N1 C13 C12 119.0(8) . . ? N1 C14 C15 103.1(7) . . ? N2 C15 C14 104.2(7) . . ? N2 C16 C17 113.1(7) . . ? C18 C17 C21 117.3(8) . . ? C18 C17 C16 123.0(7) . . ? C21 C17 C16 119.7(8) . . ? C17 C18 C19 119.8(8) . . ? N3 C19 C18 122.3(8) . . ? N3 C20 C21 123.6(8) . . ? C20 C21 C17 119.1(9) . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 23.29 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 2.32 _refine_diff_density_min -0.70 _refine_diff_density_rms 0.14 # Attachment 'Ligand.cif' data_ys02901 _database_code_depnum_ccdc_archive 'CCDC 682073' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C45 H38 B N3' _chemical_formula_weight 631.59 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21/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 10.3685(7) _cell_length_b 18.5863(11) _cell_length_c 18.5508(11) _cell_angle_alpha 90.00 _cell_angle_beta 104.445(3) _cell_angle_gamma 90.00 _cell_volume 3461.9(4) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 3714 _cell_measurement_theta_min 2.3 _cell_measurement_theta_max 19.3 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.212 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1336 _exptl_absorpt_coefficient_mu 0.070 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9793 _exptl_absorpt_correction_T_max 0.9861 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _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 'Bruker Apex CCD' _diffrn_measurement_method '\w & \p scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% none _diffrn_reflns_number 45379 _diffrn_reflns_av_R_equivalents 0.0736 _diffrn_reflns_av_sigmaI/netI 0.0400 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.58 _diffrn_reflns_theta_max 22.00 _reflns_number_total 4248 _reflns_number_gt 2842 _reflns_threshold_expression >2sigma(I) _computing_data_collection Apex _computing_cell_refinement Apex _computing_data_reduction Apex _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics Mercury _computing_publication_material Wingx _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^)+(0.0657P)^2^+0.6189P] 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 SHELXL _refine_ls_extinction_coef 0.0072(8) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 4248 _refine_ls_number_parameters 443 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0794 _refine_ls_R_factor_gt 0.0466 _refine_ls_wR_factor_ref 0.1334 _refine_ls_wR_factor_gt 0.1128 _refine_ls_goodness_of_fit_ref 1.029 _refine_ls_restrained_S_all 1.029 _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 0.58558(19) 0.06900(11) 0.41819(11) 0.0449(6) Uani 1 1 d . . . N2 N 0.5157(2) 0.09774(11) 0.29980(12) 0.0502(6) Uani 1 1 d . . . N3 N 0.2607(3) 0.06832(16) 0.21838(13) 0.0800(8) Uani 1 1 d . . . B B 0.4494(3) 0.23444(16) -0.02769(17) 0.0518(8) Uani 1 1 d . . . C1 C 0.6449(2) 0.02885(14) 0.48108(14) 0.0443(7) Uani 1 1 d . . . C2 C 0.6820(3) 0.06148(16) 0.55067(15) 0.0551(7) Uani 1 1 d . . . H2 H 0.6662 0.1113 0.5561 0.066 Uiso 1 1 calc R . . C3 C 0.7418(3) 0.02050(18) 0.61148(16) 0.0633(8) Uani 1 1 d . . . H3 H 0.7672 0.0422 0.6593 0.076 Uiso 1 1 calc R . . C4 C 0.7657(3) -0.05232(18) 0.60384(16) 0.0622(8) Uani 1 1 d . . . H4 H 0.8066 -0.0802 0.6463 0.075 Uiso 1 1 calc R . . C5 C 0.7301(3) -0.08377(16) 0.53498(16) 0.0582(8) Uani 1 1 d . . . H5 H 0.7484 -0.1334 0.5302 0.070 Uiso 1 1 calc R . . C6 C 0.6674(2) -0.04465(14) 0.47151(14) 0.0454(7) Uani 1 1 d . . . C7 C 0.6243(2) -0.07578(14) 0.39753(14) 0.0473(7) Uani 1 1 d . . . C8 C 0.6316(3) -0.14997(15) 0.38645(16) 0.0644(8) Uani 1 1 d . . . H8 H 0.6677 -0.1804 0.4277 0.077 Uiso 1 1 calc R . . C9 C 0.5875(4) -0.17945(16) 0.31679(19) 0.0794(10) Uani 1 1 d . . . H9 H 0.5927 -0.2300 0.3105 0.095 Uiso 1 1 calc R . . C10 C 0.5354(3) -0.13619(17) 0.25553(18) 0.0798(10) Uani 1 1 d . . . H10 H 0.5059 -0.1570 0.2074 0.096 Uiso 1 1 calc R . . C11 C 0.5265(3) -0.06347(16) 0.26461(15) 0.0639(8) Uani 1 1 d . . . H11 H 0.4903 -0.0340 0.2226 0.077 Uiso 1 1 calc R . . C12 C 0.5702(2) -0.03174(14) 0.33520(15) 0.0465(7) Uani 1 1 d . . . C13 C 0.5566(2) 0.04423(14) 0.34829(15) 0.0448(7) Uani 1 1 d . . . C14 C 0.5655(3) 0.14776(13) 0.41986(14) 0.0544(7) Uani 1 1 d . . . H14A H 0.6513 0.1734 0.4375 0.065 Uiso 1 1 calc R . . H14B H 0.5058 0.1607 0.4520 0.065 Uiso 1 1 calc R . . C15 C 0.5017(3) 0.16426(14) 0.33884(15) 0.0635(8) Uani 1 1 d . . . H15A H 0.4067 0.1771 0.3316 0.076 Uiso 1 1 calc R . . H15B H 0.5482 0.2044 0.3210 0.076 Uiso 1 1 calc R . . C16 C 0.4880(3) 0.09795(15) 0.21916(14) 0.0559(8) Uani 1 1 d . . . H16A H 0.5551 0.0675 0.2041 0.067 Uiso 1 1 calc R . . H16B H 0.4989 0.1476 0.2024 0.067 Uiso 1 1 calc R . . C17 C 0.3512(3) 0.07154(14) 0.17943(14) 0.0486(7) Uani 1 1 d . . . C18 C 0.3250(3) 0.05299(16) 0.10577(16) 0.0636(8) Uani 1 1 d . . . H18 H 0.3920 0.0578 0.0793 0.076 Uiso 1 1 calc R . . C19 C 0.2015(3) 0.02746(18) 0.07057(17) 0.0772(10) Uani 1 1 d . . . H19 H 0.1824 0.0129 0.0199 0.093 Uiso 1 1 calc R . . C20 C 0.1070(3) 0.0233(2) 0.10959(19) 0.0913(11) Uani 1 1 d . . . H20 H 0.0200 0.0063 0.0868 0.110 Uiso 1 1 calc R . . C21 C 0.1402(3) 0.0441(2) 0.18232(19) 0.1061(14) Uani 1 1 d . . . H21 H 0.0734 0.0413 0.2092 0.127 Uiso 1 1 calc R . . C22 C 0.4147(3) 0.25272(14) 0.05241(15) 0.0573(8) Uani 1 1 d . . . C23 C 0.5010(3) 0.29249(16) 0.10803(17) 0.0734(9) Uani 1 1 d . . . H23 H 0.5854 0.3058 0.1009 0.088 Uiso 1 1 calc R . . C24 C 0.4691(5) 0.31347(19) 0.17337(19) 0.0940(12) Uani 1 1 d . . . H24 H 0.5309 0.3409 0.2093 0.113 Uiso 1 1 calc R . . C25 C 0.3496(6) 0.2950(2) 0.1864(2) 0.1001(14) Uani 1 1 d . . . H25 H 0.3279 0.3093 0.2311 0.120 Uiso 1 1 calc R . . C26 C 0.2615(4) 0.25544(19) 0.1341(2) 0.0865(11) Uani 1 1 d . . . H26 H 0.1781 0.2420 0.1425 0.104 Uiso 1 1 calc R . . C27 C 0.2939(3) 0.23477(15) 0.06845(17) 0.0677(9) Uani 1 1 d . . . H27 H 0.2311 0.2073 0.0331 0.081 Uiso 1 1 calc R . . C28 C 0.3655(3) 0.16324(14) -0.06657(14) 0.0504(7) Uani 1 1 d . . . C29 C 0.4209(3) 0.09451(15) -0.06424(14) 0.0538(7) Uani 1 1 d . . . H29 H 0.5128 0.0887 -0.0407 0.065 Uiso 1 1 calc R . . C30 C 0.3489(3) 0.03458(16) -0.09444(16) 0.0615(8) Uani 1 1 d . . . H30 H 0.3911 -0.0111 -0.0903 0.074 Uiso 1 1 calc R . . C31 C 0.2161(3) 0.04065(18) -0.13054(16) 0.0666(9) Uani 1 1 d . . . H31 H 0.1666 -0.0003 -0.1523 0.080 Uiso 1 1 calc R . . C32 C 0.1561(3) 0.10739(19) -0.13457(17) 0.0740(9) Uani 1 1 d . . . H32 H 0.0645 0.1128 -0.1590 0.089 Uiso 1 1 calc R . . C33 C 0.2303(3) 0.16609(16) -0.10284(16) 0.0676(9) Uani 1 1 d . . . H33 H 0.1866 0.2113 -0.1058 0.081 Uiso 1 1 calc R . . C34 C 0.4122(3) 0.30584(14) -0.08239(15) 0.0519(7) Uani 1 1 d . . . C35 C 0.3701(3) 0.30160(16) -0.15963(16) 0.0670(9) Uani 1 1 d . . . H35 H 0.3573 0.2553 -0.1819 0.080 Uiso 1 1 calc R . . C36 C 0.3459(3) 0.3618(2) -0.20604(18) 0.0773(10) Uani 1 1 d . . . H36 H 0.3166 0.3558 -0.2584 0.093 Uiso 1 1 calc R . . C37 C 0.3644(3) 0.42942(19) -0.1760(2) 0.0763(10) Uani 1 1 d . . . H37 H 0.3496 0.4707 -0.2072 0.092 Uiso 1 1 calc R . . C38 C 0.4045(3) 0.43678(16) -0.1002(2) 0.0683(9) Uani 1 1 d . . . H38 H 0.4162 0.4834 -0.0786 0.082 Uiso 1 1 calc R . . C39 C 0.4279(3) 0.37653(15) -0.05504(17) 0.0584(8) Uani 1 1 d . . . H39 H 0.4562 0.3834 -0.0027 0.070 Uiso 1 1 calc R . . C40 C 0.6092(3) 0.21590(14) -0.01562(15) 0.0529(7) Uani 1 1 d . . . C41 C 0.6766(3) 0.22729(14) -0.07157(17) 0.0597(8) Uani 1 1 d . . . H41 H 0.6311 0.2514 -0.1157 0.072 Uiso 1 1 calc R . . C42 C 0.8070(3) 0.20483(16) -0.0652(2) 0.0722(9) Uani 1 1 d . . . H42 H 0.8477 0.2127 -0.1051 0.087 Uiso 1 1 calc R . . C43 C 0.8767(3) 0.17143(17) -0.0016(2) 0.0788(10) Uani 1 1 d . . . H43 H 0.9662 0.1568 0.0033 0.095 Uiso 1 1 calc R . . C44 C 0.8158(3) 0.15937(16) 0.0549(2) 0.0734(9) Uani 1 1 d . . . H44 H 0.8632 0.1362 0.0993 0.088 Uiso 1 1 calc R . . C45 C 0.6856(3) 0.18086(15) 0.04739(16) 0.0615(8) Uani 1 1 d . . . H45 H 0.6457 0.1713 0.0873 0.074 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 0.0463(13) 0.0421(14) 0.0438(14) -0.0027(11) 0.0064(10) -0.0003(10) N2 0.0537(14) 0.0430(14) 0.0493(15) 0.0003(12) 0.0042(11) 0.0014(11) N3 0.0594(18) 0.133(2) 0.0486(15) -0.0035(15) 0.0150(15) -0.0167(16) B 0.059(2) 0.046(2) 0.0491(19) 0.0014(15) 0.0116(16) 0.0049(16) C1 0.0389(16) 0.0511(19) 0.0439(18) 0.0033(14) 0.0123(13) -0.0053(13) C2 0.0526(18) 0.0591(19) 0.0521(19) -0.0044(16) 0.0105(14) -0.0057(15) C3 0.067(2) 0.074(2) 0.0486(19) 0.0000(17) 0.0128(16) -0.0083(17) C4 0.062(2) 0.074(2) 0.050(2) 0.0156(17) 0.0115(15) 0.0013(17) C5 0.0593(19) 0.0605(19) 0.056(2) 0.0117(16) 0.0169(15) 0.0058(15) C6 0.0415(16) 0.0471(18) 0.0505(18) 0.0035(14) 0.0170(13) 0.0004(13) C7 0.0472(17) 0.0449(18) 0.0527(18) 0.0014(14) 0.0179(14) 0.0051(13) C8 0.090(2) 0.046(2) 0.059(2) 0.0028(15) 0.0221(17) 0.0145(16) C9 0.119(3) 0.0449(19) 0.078(2) -0.0086(19) 0.031(2) 0.0127(19) C10 0.115(3) 0.056(2) 0.063(2) -0.0115(18) 0.0121(19) 0.0137(19) C11 0.082(2) 0.051(2) 0.0538(19) -0.0052(15) 0.0088(16) 0.0106(16) C12 0.0440(16) 0.0446(18) 0.0518(18) -0.0055(14) 0.0137(13) 0.0038(13) C13 0.0364(15) 0.0472(18) 0.0494(18) 0.0010(15) 0.0081(13) -0.0001(13) C14 0.0621(19) 0.0385(17) 0.0595(19) -0.0027(13) 0.0093(15) -0.0015(14) C15 0.076(2) 0.0448(18) 0.062(2) -0.0031(15) 0.0021(16) 0.0013(15) C16 0.0575(19) 0.0603(19) 0.0484(18) 0.0056(14) 0.0100(14) -0.0026(15) C17 0.0509(18) 0.0493(17) 0.0438(18) 0.0095(13) 0.0086(15) 0.0051(14) C18 0.057(2) 0.085(2) 0.0480(19) -0.0018(16) 0.0136(16) 0.0040(17) C19 0.069(2) 0.109(3) 0.0472(19) -0.0105(18) 0.0008(19) 0.001(2) C20 0.061(2) 0.146(3) 0.060(2) -0.002(2) 0.0023(19) -0.024(2) C21 0.059(2) 0.198(4) 0.062(3) -0.007(3) 0.0173(19) -0.028(3) C22 0.070(2) 0.0490(18) 0.0535(19) 0.0062(15) 0.0162(17) 0.0125(16) C23 0.093(2) 0.071(2) 0.055(2) -0.0116(17) 0.0162(19) 0.0041(19) C24 0.136(4) 0.081(3) 0.058(2) -0.0085(19) 0.013(2) 0.019(3) C25 0.163(5) 0.087(3) 0.061(3) 0.014(2) 0.047(3) 0.041(3) C26 0.115(3) 0.077(3) 0.084(3) 0.026(2) 0.056(3) 0.033(2) C27 0.081(2) 0.058(2) 0.068(2) 0.0139(16) 0.0265(18) 0.0160(17) C28 0.058(2) 0.0496(19) 0.0440(16) 0.0017(13) 0.0128(14) 0.0041(15) C29 0.0587(18) 0.0518(19) 0.0535(18) -0.0013(14) 0.0185(14) 0.0028(16) C30 0.069(2) 0.054(2) 0.067(2) -0.0073(16) 0.0271(18) 0.0000(17) C31 0.082(3) 0.063(2) 0.056(2) -0.0100(16) 0.0200(18) -0.0172(19) C32 0.068(2) 0.076(3) 0.070(2) 0.0074(18) 0.0026(17) -0.007(2) C33 0.067(2) 0.053(2) 0.075(2) 0.0039(16) 0.0035(18) 0.0064(17) C34 0.0550(18) 0.0510(19) 0.0531(19) 0.0004(14) 0.0200(14) 0.0056(14) C35 0.086(2) 0.060(2) 0.057(2) 0.0042(16) 0.0211(17) 0.0144(17) C36 0.089(3) 0.084(3) 0.062(2) 0.018(2) 0.0243(18) 0.023(2) C37 0.075(2) 0.070(3) 0.093(3) 0.032(2) 0.039(2) 0.0223(19) C38 0.066(2) 0.051(2) 0.095(3) 0.0097(19) 0.0345(19) 0.0056(16) C39 0.0566(19) 0.053(2) 0.068(2) 0.0020(17) 0.0202(15) 0.0010(15) C40 0.0606(19) 0.0428(17) 0.0517(18) -0.0022(14) 0.0071(16) -0.0033(14) C41 0.067(2) 0.0455(18) 0.066(2) -0.0050(14) 0.0163(17) -0.0050(15) C42 0.072(2) 0.060(2) 0.092(3) -0.0024(18) 0.035(2) -0.0035(18) C43 0.060(2) 0.064(2) 0.111(3) -0.004(2) 0.019(2) 0.0011(18) C44 0.064(2) 0.063(2) 0.083(2) 0.0042(17) 0.000(2) 0.0055(18) C45 0.062(2) 0.0560(19) 0.064(2) 0.0017(15) 0.0117(16) -0.0020(16) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C13 1.338(3) . ? N1 C1 1.392(3) . ? N1 C14 1.480(3) . ? N2 C13 1.337(3) . ? N2 C16 1.451(3) . ? N2 C15 1.458(3) . ? N3 C17 1.321(3) . ? N3 C21 1.340(4) . ? B C28 1.648(4) . ? B C22 1.649(4) . ? B C40 1.652(4) . ? B C34 1.656(4) . ? C1 C2 1.391(3) . ? C1 C6 1.405(3) . ? C2 C3 1.374(4) . ? C3 C4 1.390(4) . ? C4 C5 1.369(4) . ? C5 C6 1.398(3) . ? C6 C7 1.453(3) . ? C7 C8 1.399(4) . ? C7 C12 1.413(3) . ? C8 C9 1.373(4) . ? C9 C10 1.387(4) . ? C10 C11 1.368(4) . ? C11 C12 1.404(3) . ? C12 C13 1.446(4) . ? C14 C15 1.515(3) . ? C16 C17 1.508(4) . ? C17 C18 1.369(4) . ? C18 C19 1.368(4) . ? C19 C20 1.358(4) . ? C20 C21 1.363(4) . ? C22 C23 1.397(4) . ? C22 C27 1.398(4) . ? C23 C24 1.390(5) . ? C24 C25 1.364(5) . ? C25 C26 1.369(5) . ? C26 C27 1.395(4) . ? C28 C29 1.397(3) . ? C28 C33 1.397(4) . ? C29 C30 1.380(4) . ? C30 C31 1.378(4) . ? C31 C32 1.381(4) . ? C32 C33 1.379(4) . ? C34 C35 1.392(4) . ? C34 C39 1.403(4) . ? C35 C36 1.396(4) . ? C36 C37 1.369(4) . ? C37 C38 1.370(4) . ? C38 C39 1.383(4) . ? C40 C45 1.399(4) . ? C40 C41 1.404(4) . ? C41 C42 1.392(4) . ? C42 C43 1.370(4) . ? C43 C44 1.370(4) . ? C44 C45 1.381(4) . ? 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 C13 N1 C1 125.0(2) . . ? C13 N1 C14 111.2(2) . . ? C1 N1 C14 123.2(2) . . ? C13 N2 C16 130.1(2) . . ? C13 N2 C15 110.5(2) . . ? C16 N2 C15 119.4(2) . . ? C17 N3 C21 116.3(3) . . ? C28 B C22 110.5(2) . . ? C28 B C40 107.1(2) . . ? C22 B C40 111.0(2) . . ? C28 B C34 111.0(2) . . ? C22 B C34 108.5(2) . . ? C40 B C34 108.8(2) . . ? C2 C1 N1 120.4(2) . . ? C2 C1 C6 121.7(2) . . ? N1 C1 C6 117.9(2) . . ? C3 C2 C1 118.9(3) . . ? C2 C3 C4 120.8(3) . . ? C5 C4 C3 119.8(3) . . ? C4 C5 C6 121.6(3) . . ? C5 C6 C1 117.1(2) . . ? C5 C6 C7 123.9(3) . . ? C1 C6 C7 119.0(2) . . ? C8 C7 C12 118.4(2) . . ? C8 C7 C6 121.1(2) . . ? C12 C7 C6 120.5(2) . . ? C9 C8 C7 120.9(3) . . ? C8 C9 C10 120.7(3) . . ? C11 C10 C9 119.8(3) . . ? C10 C11 C12 120.9(3) . . ? C11 C12 C7 119.3(2) . . ? C11 C12 C13 123.0(2) . . ? C7 C12 C13 117.6(2) . . ? N2 C13 N1 110.7(2) . . ? N2 C13 C12 129.9(2) . . ? N1 C13 C12 119.4(2) . . ? N1 C14 C15 102.0(2) . . ? N2 C15 C14 104.4(2) . . ? N2 C16 C17 115.0(2) . . ? N3 C17 C18 122.9(3) . . ? N3 C17 C16 117.2(2) . . ? C18 C17 C16 119.9(3) . . ? C19 C18 C17 119.5(3) . . ? C20 C19 C18 118.6(3) . . ? C19 C20 C21 118.3(3) . . ? N3 C21 C20 124.3(3) . . ? C23 C22 C27 114.3(3) . . ? C23 C22 B 122.1(3) . . ? C27 C22 B 123.4(3) . . ? C24 C23 C22 123.0(4) . . ? C25 C24 C23 120.6(4) . . ? C24 C25 C26 119.0(4) . . ? C25 C26 C27 120.2(4) . . ? C26 C27 C22 122.9(3) . . ? C29 C28 C33 113.9(3) . . ? C29 C28 B 123.6(2) . . ? C33 C28 B 122.5(2) . . ? C30 C29 C28 123.3(3) . . ? C31 C30 C29 120.4(3) . . ? C30 C31 C32 118.8(3) . . ? C33 C32 C31 119.5(3) . . ? C32 C33 C28 124.2(3) . . ? C35 C34 C39 113.8(2) . . ? C35 C34 B 123.4(2) . . ? C39 C34 B 122.7(2) . . ? C34 C35 C36 123.5(3) . . ? C37 C36 C35 120.0(3) . . ? C36 C37 C38 119.1(3) . . ? C37 C38 C39 120.2(3) . . ? C38 C39 C34 123.5(3) . . ? C45 C40 C41 113.9(3) . . ? C45 C40 B 123.4(3) . . ? C41 C40 B 122.4(2) . . ? C42 C41 C40 123.0(3) . . ? C43 C42 C41 120.1(3) . . ? C42 C43 C44 119.3(3) . . ? C43 C44 C45 120.1(3) . . ? C44 C45 C40 123.7(3) . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 22.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.43 _refine_diff_density_min -0.13 _refine_diff_density_rms 0.03