# Supplementary Material (ESI) for Dalton Transactions # This journal is (c) The Royal Society of Chemistry 2009 data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 _publ_contact_author_name 'Peter Hofmann' _publ_contact_author_email PH@OCI.UNI-HEIDELBERG.DE _publ_section_title ; Reversible Substrate Binding at Copper Centers in Neutral Copper(I) Carbene Complexes Derived from Bis(3-tert-butylimidazole-2-ylidene)methane ; loop_ _publ_author_name 'Peter Hofmann' 'Frank Rominger' 'Igor V Shishkov' # Attachment 'ivsh_Dalton_081.cif' data_ivsh11 _database_code_depnum_ccdc_archive 'CCDC 697052' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 'in paper 3' _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 H24 Br2 Cu2 N4' _chemical_formula_weight 547.28 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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' _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 24.9319(7) _cell_length_b 10.6376(3) _cell_length_c 15.3725(4) _cell_angle_alpha 90.00 _cell_angle_beta 107.8060(10) _cell_angle_gamma 90.00 _cell_volume 3881.72(18) _cell_formula_units_Z 8 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description polyhedron _exptl_crystal_colour colorless _exptl_crystal_size_max 0.42 _exptl_crystal_size_mid 0.1 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.873 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2160 _exptl_absorpt_coefficient_mu 6.312 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.53 _exptl_absorpt_correction_T_max 0.90 _exptl_absorpt_process_details 'Blessing, Acta Cryst. (1995) A51 33-38.' _exptl_special_details ; ? ; _diffrn_ambient_temperature 200(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 19536 _diffrn_reflns_av_R_equivalents 0.0466 _diffrn_reflns_av_sigmaI/netI 0.0444 _diffrn_reflns_limit_h_min -32 _diffrn_reflns_limit_h_max 32 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.72 _diffrn_reflns_theta_max 27.47 _reflns_number_total 4442 _reflns_number_gt 3097 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0309P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4442 _refine_ls_number_parameters 215 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0537 _refine_ls_R_factor_gt 0.0290 _refine_ls_wR_factor_ref 0.0686 _refine_ls_wR_factor_gt 0.0615 _refine_ls_goodness_of_fit_ref 0.989 _refine_ls_restrained_S_all 0.989 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu 0.082415(15) 0.15585(3) 0.12009(2) 0.02628(10) Uani 1 1 d . . . Cu2 Cu 0.083549(15) 0.34464(3) -0.03898(2) 0.02616(10) Uani 1 1 d . . . Br1 Br 0.004832(12) 0.25161(4) 0.00188(2) 0.04126(11) Uani 1 1 d . . . Br2 Br 0.161690(11) 0.25002(3) 0.080178(19) 0.02652(9) Uani 1 1 d . . . C1 C 0.08381(11) 0.0649(2) 0.22816(18) 0.0188(6) Uani 1 1 d . . . N2 N 0.11911(10) -0.0247(2) 0.27752(16) 0.0215(5) Uani 1 1 d . . . C3 C 0.10759(13) -0.0490(3) 0.3589(2) 0.0315(7) Uani 1 1 d . . . H3 H 0.1271 -0.1067 0.4050 0.038 Uiso 1 1 calc R . . C4 C 0.06395(13) 0.0237(3) 0.3606(2) 0.0327(8) Uani 1 1 d . . . H4 H 0.0462 0.0270 0.4071 0.039 Uiso 1 1 calc R . . N5 N 0.05010(9) 0.0930(2) 0.28077(15) 0.0206(5) Uani 1 1 d . . . C5 C 0.0000 0.1715(4) 0.2500 0.0218(9) Uani 1 2 d S . . H5A H 0.0026 0.2261 0.1993 0.026 Uiso 0.50 1 calc PR . . H5B H -0.0026 0.2261 0.3007 0.026 Uiso 0.50 1 calc PR . . C6 C 0.08435(11) 0.4348(2) -0.14655(18) 0.0189(6) Uani 1 1 d . . . N7 N 0.11973(9) 0.5244(2) -0.16144(15) 0.0199(5) Uani 1 1 d . . . C8 C 0.10726(13) 0.5493(3) -0.2541(2) 0.0301(7) Uani 1 1 d . . . H8 H 0.1264 0.6072 -0.2813 0.036 Uiso 1 1 calc R . . C9 C 0.06342(13) 0.4770(3) -0.2984(2) 0.0293(7) Uani 1 1 d . . . H9 H 0.0452 0.4740 -0.3624 0.035 Uiso 1 1 calc R . . N10 N 0.05009(9) 0.4079(2) -0.23194(15) 0.0196(5) Uani 1 1 d . . . C10 C 0.0000 0.3284(4) -0.2500 0.0215(9) Uani 1 2 d S . . H10A H -0.0029 0.2738 -0.3034 0.026 Uiso 0.50 1 calc PR . . H10B H 0.0029 0.2738 -0.1966 0.026 Uiso 0.50 1 calc PR . . C11 C 0.16654(11) -0.0840(3) 0.2514(2) 0.0244(7) Uani 1 1 d . . . C12 C 0.14804(14) -0.1085(3) 0.1488(2) 0.0401(9) Uani 1 1 d . . . H12A H 0.1129 -0.1569 0.1314 0.060 Uiso 1 1 calc R . . H12B H 0.1774 -0.1562 0.1329 0.060 Uiso 1 1 calc R . . H12C H 0.1419 -0.0282 0.1160 0.060 Uiso 1 1 calc R . . C13 C 0.18163(14) -0.2092(3) 0.3023(3) 0.0458(10) Uani 1 1 d . . . H13A H 0.1938 -0.1937 0.3683 0.069 Uiso 1 1 calc R . . H13B H 0.2122 -0.2497 0.2851 0.069 Uiso 1 1 calc R . . H13C H 0.1485 -0.2642 0.2861 0.069 Uiso 1 1 calc R . . C14 C 0.21660(12) 0.0044(3) 0.2791(2) 0.0270(7) Uani 1 1 d . . . H14A H 0.2065 0.0844 0.2465 0.040 Uiso 1 1 calc R . . H14B H 0.2483 -0.0334 0.2635 0.040 Uiso 1 1 calc R . . H14C H 0.2274 0.0194 0.3451 0.040 Uiso 1 1 calc R . . C15 C 0.16740(11) 0.5827(3) -0.0886(2) 0.0230(6) Uani 1 1 d . . . C16 C 0.18441(14) 0.7048(3) -0.1260(2) 0.0386(8) Uani 1 1 d . . . H16A H 0.1995 0.6852 -0.1764 0.058 Uiso 1 1 calc R . . H16B H 0.2133 0.7479 -0.0773 0.058 Uiso 1 1 calc R . . H16C H 0.1514 0.7593 -0.1483 0.058 Uiso 1 1 calc R . . C17 C 0.14873(13) 0.6129(3) -0.0057(2) 0.0362(8) Uani 1 1 d . . . H17A H 0.1147 0.6650 -0.0244 0.054 Uiso 1 1 calc R . . H17B H 0.1788 0.6587 0.0393 0.054 Uiso 1 1 calc R . . H17C H 0.1407 0.5346 0.0215 0.054 Uiso 1 1 calc R . . C18 C 0.21681(12) 0.4921(3) -0.0641(2) 0.0251(7) Uani 1 1 d . . . H18A H 0.2064 0.4153 -0.0380 0.038 Uiso 1 1 calc R . . H18B H 0.2491 0.5315 -0.0193 0.038 Uiso 1 1 calc R . . H18C H 0.2268 0.4710 -0.1193 0.038 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 0.0290(2) 0.0293(2) 0.0235(2) 0.00490(16) 0.01242(17) 0.00272(16) Cu2 0.0292(2) 0.0295(2) 0.0187(2) 0.00298(15) 0.00562(16) -0.00168(16) Br1 0.01661(16) 0.0684(2) 0.0368(2) 0.02529(17) 0.00520(14) 0.00041(15) Br2 0.01656(15) 0.03734(17) 0.02457(17) 0.00936(13) 0.00465(12) -0.00075(13) C1 0.0123(13) 0.0213(15) 0.0230(15) 0.0003(12) 0.0057(12) -0.0015(11) N2 0.0149(12) 0.0226(12) 0.0267(14) 0.0060(10) 0.0060(11) 0.0011(10) C3 0.0283(18) 0.0393(19) 0.0273(17) 0.0149(15) 0.0092(14) 0.0033(15) C4 0.0296(19) 0.0441(19) 0.0269(18) 0.0104(15) 0.0124(15) 0.0018(15) N5 0.0153(12) 0.0270(13) 0.0208(13) 0.0023(10) 0.0072(10) -0.0009(10) C5 0.0151(19) 0.021(2) 0.030(2) 0.000 0.0083(18) 0.000 C6 0.0142(14) 0.0201(15) 0.0201(15) 0.0013(12) 0.0020(12) 0.0024(11) N7 0.0165(12) 0.0209(12) 0.0208(13) 0.0015(10) 0.0035(10) -0.0023(10) C8 0.0292(18) 0.0352(18) 0.0251(17) 0.0083(14) 0.0071(14) -0.0044(14) C9 0.0269(18) 0.0383(18) 0.0191(16) 0.0056(14) 0.0019(14) -0.0037(14) N10 0.0146(12) 0.0257(13) 0.0167(13) 0.0013(10) 0.0019(10) -0.0011(10) C10 0.0137(19) 0.023(2) 0.024(2) 0.000 -0.0001(17) 0.000 C11 0.0153(14) 0.0193(15) 0.0384(18) 0.0034(13) 0.0080(13) 0.0037(11) C12 0.0290(18) 0.0401(19) 0.048(2) -0.0206(17) 0.0077(16) 0.0050(15) C13 0.0301(19) 0.0284(17) 0.084(3) 0.0200(19) 0.024(2) 0.0084(15) C14 0.0194(16) 0.0283(17) 0.0336(19) -0.0002(13) 0.0088(14) 0.0002(12) C15 0.0158(14) 0.0216(15) 0.0273(16) -0.0016(13) 0.0003(12) -0.0026(12) C16 0.0342(19) 0.0248(16) 0.045(2) 0.0059(15) -0.0052(17) -0.0064(15) C17 0.0267(17) 0.0400(18) 0.040(2) -0.0192(16) 0.0076(15) -0.0012(14) C18 0.0185(16) 0.0278(16) 0.0259(17) 0.0000(13) 0.0021(13) -0.0007(12) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 C1 1.913(3) . ? Cu1 Br1 2.4355(5) . ? Cu1 Br2 2.4552(4) . ? Cu2 C6 1.917(3) . ? Cu2 Br1 2.4453(5) . ? Cu2 Br2 2.4457(4) . ? C1 N2 1.361(3) . ? C1 N5 1.366(3) . ? N2 C3 1.391(4) . ? N2 C11 1.499(3) . ? C3 C4 1.342(4) . ? C4 N5 1.382(4) . ? N5 C5 1.456(3) . ? C5 N5 1.456(3) 2 ? C6 N10 1.360(3) . ? C6 N7 1.365(3) . ? N7 C8 1.388(4) . ? N7 C15 1.495(3) . ? C8 C9 1.340(4) . ? C9 N10 1.380(4) . ? N10 C10 1.463(3) . ? C10 N10 1.463(3) 2_554 ? C11 C14 1.516(4) . ? C11 C12 1.524(4) . ? C11 C13 1.532(4) . ? C15 C18 1.518(4) . ? C15 C17 1.520(4) . ? C15 C16 1.532(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 C1 Cu1 Br1 131.19(8) . . ? C1 Cu1 Br2 128.39(8) . . ? Br1 Cu1 Br2 99.164(16) . . ? C6 Cu2 Br1 130.16(8) . . ? C6 Cu2 Br2 129.49(8) . . ? Br1 Cu2 Br2 99.157(16) . . ? Cu1 Br1 Cu2 81.039(14) . . ? Cu2 Br2 Cu1 80.638(14) . . ? N2 C1 N5 103.5(2) . . ? N2 C1 Cu1 132.48(19) . . ? N5 C1 Cu1 123.55(19) . . ? C1 N2 C3 110.8(2) . . ? C1 N2 C11 125.0(2) . . ? C3 N2 C11 124.0(2) . . ? C4 C3 N2 107.6(3) . . ? C3 C4 N5 105.9(3) . . ? C1 N5 C4 112.2(2) . . ? C1 N5 C5 123.7(2) . . ? C4 N5 C5 123.4(2) . . ? N5 C5 N5 110.0(3) . 2 ? N10 C6 N7 103.5(2) . . ? N10 C6 Cu2 123.94(19) . . ? N7 C6 Cu2 132.2(2) . . ? C6 N7 C8 110.6(2) . . ? C6 N7 C15 124.8(2) . . ? C8 N7 C15 124.5(2) . . ? C9 C8 N7 107.7(3) . . ? C8 C9 N10 105.9(3) . . ? C6 N10 C9 112.3(2) . . ? C6 N10 C10 123.56(19) . . ? C9 N10 C10 123.5(2) . . ? N10 C10 N10 109.4(3) 2_554 . ? N2 C11 C14 108.2(2) . . ? N2 C11 C12 109.6(2) . . ? C14 C11 C12 111.1(3) . . ? N2 C11 C13 108.6(2) . . ? C14 C11 C13 110.1(2) . . ? C12 C11 C13 109.2(3) . . ? N7 C15 C18 108.8(2) . . ? N7 C15 C17 109.8(2) . . ? C18 C15 C17 111.1(2) . . ? N7 C15 C16 108.6(2) . . ? C18 C15 C16 109.5(2) . . ? C17 C15 C16 109.1(2) . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 27.47 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.490 _refine_diff_density_min -0.672 _refine_diff_density_rms 0.097 #===END data_ivsh9 _database_code_depnum_ccdc_archive 'CCDC 697053' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 'in paper 6' _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H36 Br2 Cu2 N6' _chemical_formula_weight 671.47 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 14.9568(3) _cell_length_b 9.65930(10) _cell_length_c 19.61520(10) _cell_angle_alpha 90.00 _cell_angle_beta 106.1740(10) _cell_angle_gamma 90.00 _cell_volume 2721.69(6) _cell_formula_units_Z 4 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description polyhedron _exptl_crystal_colour colorless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.639 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1352 _exptl_absorpt_coefficient_mu 4.520 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.4651 _exptl_absorpt_correction_T_max 0.7732 _exptl_absorpt_process_details 'Blessing, Acta Cryst. (1995) A51 33-38.' _exptl_special_details ; ? ; _diffrn_ambient_temperature 200(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 20742 _diffrn_reflns_av_R_equivalents 0.0657 _diffrn_reflns_av_sigmaI/netI 0.0543 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 1.42 _diffrn_reflns_theta_max 24.10 _reflns_number_total 4311 _reflns_number_gt 3158 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0536P)^2^+39.6095P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4311 _refine_ls_number_parameters 293 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0877 _refine_ls_R_factor_gt 0.0612 _refine_ls_wR_factor_ref 0.1797 _refine_ls_wR_factor_gt 0.1684 _refine_ls_goodness_of_fit_ref 1.152 _refine_ls_restrained_S_all 1.152 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu 0.21098(9) 0.58431(15) 0.44824(7) 0.0347(4) Uani 1 1 d . . . Cu2 Cu 0.35143(9) 0.66440(13) 0.37761(6) 0.0295(3) Uani 1 1 d . . . Br1 Br 0.19349(8) 0.76035(12) 0.35021(6) 0.0370(3) Uani 1 1 d . . . Br2 Br 0.36040(9) 0.50975(12) 0.28359(6) 0.0389(3) Uani 1 1 d . . . C1 C 0.2637(6) 0.6425(10) 0.5449(5) 0.022(2) Uani 1 1 d . . . N2 N 0.3533(5) 0.6197(8) 0.5802(4) 0.0203(18) Uani 1 1 d . . . C3 C 0.3719(6) 0.6634(10) 0.6509(5) 0.019(2) Uani 1 1 d . . . H3 H 0.4298 0.6581 0.6865 0.022 Uiso 1 1 calc R . . C4 C 0.2922(7) 0.7138(11) 0.6581(5) 0.028(2) Uani 1 1 d . . . H4 H 0.2824 0.7509 0.7003 0.033 Uiso 1 1 calc R . . N5 N 0.2264(6) 0.7024(8) 0.5934(4) 0.0231(19) Uani 1 1 d . . . C6 C 0.1290(7) 0.7559(12) 0.5764(6) 0.032(3) Uani 1 1 d . . . C7 C 0.1062(9) 0.7870(15) 0.6455(7) 0.051(3) Uani 1 1 d . . . H7A H 0.1107 0.7017 0.6733 0.076 Uiso 1 1 calc R . . H7B H 0.0428 0.8239 0.6352 0.076 Uiso 1 1 calc R . . H7C H 0.1503 0.8554 0.6726 0.076 Uiso 1 1 calc R . . C8 C 0.0619(10) 0.6470(19) 0.5341(9) 0.078(5) Uani 1 1 d . . . H8A H 0.0661 0.5628 0.5627 0.117 Uiso 1 1 calc R . . H8B H 0.0784 0.6255 0.4903 0.117 Uiso 1 1 calc R . . H8C H -0.0019 0.6830 0.5223 0.117 Uiso 1 1 calc R . . C9 C 0.1233(10) 0.8870(16) 0.5330(8) 0.069(5) Uani 1 1 d . . . H9A H 0.1376 0.8656 0.4883 0.104 Uiso 1 1 calc R . . H9B H 0.1682 0.9548 0.5598 0.104 Uiso 1 1 calc R . . H9C H 0.0603 0.9254 0.5227 0.104 Uiso 1 1 calc R . . C10 C 0.4216(7) 0.5608(10) 0.5488(5) 0.023(2) Uani 1 1 d . . . H10A H 0.3894 0.5015 0.5082 0.028 Uiso 1 1 calc R . . H10B H 0.4646 0.5014 0.5844 0.028 Uiso 1 1 calc R . . C11 C 0.4544(7) 0.7157(10) 0.4561(5) 0.023(2) Uani 1 1 d . . . N12 N 0.4750(5) 0.6654(8) 0.5244(4) 0.0214(18) Uani 1 1 d . . . C13 C 0.5572(7) 0.7194(11) 0.5665(5) 0.028(2) Uani 1 1 d . . . H13 H 0.5851 0.6996 0.6152 0.034 Uiso 1 1 calc R . . C14 C 0.5902(7) 0.8046(11) 0.5259(6) 0.032(3) Uani 1 1 d . . . H14 H 0.6464 0.8561 0.5398 0.039 Uiso 1 1 calc R . . N15 N 0.5265(5) 0.8033(8) 0.4597(4) 0.0229(19) Uani 1 1 d . . . C16 C 0.5458(7) 0.8702(11) 0.3948(6) 0.030(2) Uani 1 1 d . . . C17 C 0.5887(11) 0.7612(12) 0.3576(7) 0.056(4) Uani 1 1 d . . . H17A H 0.5447 0.6846 0.3423 0.083 Uiso 1 1 calc R . . H17B H 0.6462 0.7263 0.3904 0.083 Uiso 1 1 calc R . . H17C H 0.6027 0.8025 0.3161 0.083 Uiso 1 1 calc R . . C18 C 0.4556(8) 0.9261(12) 0.3458(6) 0.040(3) Uani 1 1 d . . . H18A H 0.4119 0.8496 0.3294 0.060 Uiso 1 1 calc R . . H18B H 0.4685 0.9714 0.3049 0.060 Uiso 1 1 calc R . . H18C H 0.4283 0.9933 0.3717 0.060 Uiso 1 1 calc R . . C19 C 0.6129(8) 0.9908(12) 0.4201(7) 0.044(3) Uani 1 1 d . . . H19A H 0.5839 1.0594 0.4440 0.067 Uiso 1 1 calc R . . H19B H 0.6275 1.0338 0.3792 0.067 Uiso 1 1 calc R . . H19C H 0.6703 0.9565 0.4533 0.067 Uiso 1 1 calc R . . C21 C 0.1587(8) 0.3880(12) 0.3288(6) 0.034(3) Uani 1 1 d . . . H21 H 0.169(8) 0.463(13) 0.295(6) 0.05(3) Uiso 1 1 d . . . N22 N 0.1719(6) 0.4088(9) 0.3977(5) 0.030(2) Uani 1 1 d . . . C23 C 0.1726(8) 0.2792(13) 0.4260(6) 0.039(3) Uani 1 1 d . . . H23 H 0.1808 0.2600 0.4748 0.047 Uiso 1 1 calc R . . C24 C 0.1599(7) 0.1832(12) 0.3747(6) 0.036(3) Uani 1 1 d . . . H24 H 0.1582 0.0857 0.3804 0.043 Uiso 1 1 calc R . . N25 N 0.1500(6) 0.2532(9) 0.3126(4) 0.030(2) Uani 1 1 d . . . C26 C 0.1386(8) 0.1890(11) 0.2416(6) 0.036(3) Uani 1 1 d . . . C27 C 0.1182(11) 0.3010(13) 0.1845(6) 0.062(4) Uani 1 1 d . . . H27A H 0.0617 0.3514 0.1857 0.093 Uiso 1 1 calc R . . H27B H 0.1089 0.2582 0.1378 0.093 Uiso 1 1 calc R . . H27C H 0.1707 0.3656 0.1935 0.093 Uiso 1 1 calc R . . C28 C 0.0538(9) 0.0893(13) 0.2267(7) 0.052(3) Uani 1 1 d . . . H28A H -0.0022 0.1416 0.2273 0.078 Uiso 1 1 calc R . . H28B H 0.0653 0.0174 0.2634 0.078 Uiso 1 1 calc R . . H28C H 0.0446 0.0461 0.1801 0.078 Uiso 1 1 calc R . . C29 C 0.2266(9) 0.1118(13) 0.2411(7) 0.048(3) Uani 1 1 d . . . H29A H 0.2393 0.0401 0.2779 0.072 Uiso 1 1 calc R . . H29B H 0.2790 0.1768 0.2506 0.072 Uiso 1 1 calc R . . H29C H 0.2186 0.0686 0.1946 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 Cu1 0.0271(7) 0.0492(9) 0.0266(7) -0.0129(6) 0.0054(6) 0.0023(6) Cu2 0.0304(7) 0.0319(7) 0.0228(7) 0.0029(6) 0.0016(5) -0.0015(6) Br1 0.0342(6) 0.0369(7) 0.0364(6) 0.0031(5) 0.0039(5) 0.0093(5) Br2 0.0537(7) 0.0364(6) 0.0262(6) 0.0010(5) 0.0107(5) 0.0116(6) C1 0.019(5) 0.024(5) 0.022(5) 0.003(4) 0.005(4) 0.001(4) N2 0.026(5) 0.022(4) 0.015(4) -0.003(3) 0.009(3) -0.003(3) C3 0.021(5) 0.024(5) 0.011(4) 0.005(4) 0.005(4) 0.004(4) C4 0.030(6) 0.031(6) 0.023(5) 0.000(5) 0.009(5) -0.006(5) N5 0.030(5) 0.021(4) 0.023(4) -0.009(4) 0.015(4) -0.004(4) C6 0.018(5) 0.041(7) 0.041(6) -0.005(5) 0.015(5) 0.004(5) C7 0.036(7) 0.067(9) 0.054(8) -0.008(7) 0.020(6) 0.005(6) C8 0.039(8) 0.111(14) 0.087(12) -0.044(11) 0.022(8) -0.013(9) C9 0.049(9) 0.079(11) 0.084(11) 0.027(9) 0.025(8) 0.042(8) C10 0.026(5) 0.017(5) 0.025(5) -0.002(4) 0.005(4) 0.005(4) C11 0.023(5) 0.022(5) 0.027(5) 0.000(4) 0.013(4) 0.010(4) N12 0.026(5) 0.020(4) 0.021(4) 0.002(4) 0.011(4) 0.004(4) C13 0.028(6) 0.038(6) 0.018(5) 0.004(5) 0.007(4) 0.007(5) C14 0.029(6) 0.027(6) 0.046(7) 0.002(5) 0.017(5) -0.002(5) N15 0.019(4) 0.024(5) 0.027(5) 0.003(4) 0.007(4) 0.005(4) C16 0.037(6) 0.027(6) 0.034(6) 0.011(5) 0.022(5) 0.003(5) C17 0.101(11) 0.027(6) 0.070(9) 0.013(6) 0.075(9) 0.015(7) C18 0.058(8) 0.032(6) 0.029(6) 0.005(5) 0.012(6) -0.005(6) C19 0.048(7) 0.029(6) 0.064(8) 0.013(6) 0.028(6) -0.011(6) C21 0.031(6) 0.036(7) 0.031(6) -0.013(5) 0.005(5) -0.006(5) N22 0.026(5) 0.034(5) 0.033(5) -0.003(4) 0.013(4) -0.002(4) C23 0.039(7) 0.047(7) 0.031(6) 0.005(6) 0.007(5) 0.003(6) C24 0.032(6) 0.033(6) 0.043(7) 0.010(6) 0.010(5) 0.000(5) N25 0.030(5) 0.027(5) 0.028(5) -0.004(4) 0.001(4) 0.000(4) C26 0.039(7) 0.028(6) 0.035(6) -0.014(5) 0.000(5) 0.000(5) C27 0.109(12) 0.038(7) 0.020(6) -0.003(5) -0.011(7) 0.012(8) C28 0.041(7) 0.045(8) 0.065(9) -0.019(7) 0.006(6) -0.010(6) C29 0.053(8) 0.043(7) 0.054(8) -0.003(6) 0.022(7) -0.001(6) _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 C1 1.923(9) . ? Cu1 N22 1.969(9) . ? Cu1 Br1 2.5254(18) . ? Cu1 Cu2 2.9244(19) . ? Cu2 C11 1.915(10) . ? Cu2 Br2 2.4059(17) . ? Cu2 Br1 2.4537(17) . ? C1 N2 1.344(12) . ? C1 N5 1.358(12) . ? N2 C3 1.401(11) . ? N2 C10 1.448(12) . ? C3 C4 1.332(14) . ? C4 N5 1.377(13) . ? N5 C6 1.494(13) . ? C6 C9 1.515(18) . ? C6 C7 1.517(15) . ? C6 C8 1.529(18) . ? C10 N12 1.450(12) . ? C11 N15 1.356(13) . ? C11 N12 1.377(12) . ? N12 C13 1.379(13) . ? C13 C14 1.330(14) . ? C14 N15 1.380(13) . ? N15 C16 1.526(12) . ? C16 C17 1.520(15) . ? C16 C18 1.521(15) . ? C16 C19 1.527(15) . ? C21 N22 1.325(14) . ? C21 N25 1.338(14) . ? N22 C23 1.368(14) . ? C23 C24 1.343(16) . ? C24 N25 1.364(14) . ? N25 C26 1.491(13) . ? C26 C29 1.516(16) . ? C26 C27 1.525(16) . ? C26 C28 1.554(16) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 Cu1 N22 137.0(4) . . ? C1 Cu1 Br1 118.7(3) . . ? N22 Cu1 Br1 104.1(3) . . ? C1 Cu1 Cu2 103.8(3) . . ? N22 Cu1 Cu2 98.1(2) . . ? Br1 Cu1 Cu2 52.90(4) . . ? C11 Cu2 Br2 124.9(3) . . ? C11 Cu2 Br1 126.0(3) . . ? Br2 Cu2 Br1 108.81(6) . . ? C11 Cu2 Cu1 102.2(3) . . ? Br2 Cu2 Cu1 113.56(6) . . ? Br1 Cu2 Cu1 55.18(5) . . ? Cu2 Br1 Cu1 71.92(5) . . ? N2 C1 N5 104.7(8) . . ? N2 C1 Cu1 122.4(7) . . ? N5 C1 Cu1 132.8(7) . . ? C1 N2 C3 110.8(8) . . ? C1 N2 C10 124.5(8) . . ? C3 N2 C10 124.7(8) . . ? C4 C3 N2 106.2(8) . . ? C3 C4 N5 107.6(9) . . ? C1 N5 C4 110.7(8) . . ? C1 N5 C6 123.8(8) . . ? C4 N5 C6 125.4(8) . . ? N5 C6 C9 108.3(9) . . ? N5 C6 C7 108.5(9) . . ? C9 C6 C7 110.2(10) . . ? N5 C6 C8 109.6(9) . . ? C9 C6 C8 110.2(12) . . ? C7 C6 C8 110.1(10) . . ? N2 C10 N12 112.7(7) . . ? N15 C11 N12 102.2(8) . . ? N15 C11 Cu2 130.8(7) . . ? N12 C11 Cu2 127.0(7) . . ? C11 N12 C13 111.6(8) . . ? C11 N12 C10 125.0(8) . . ? C13 N12 C10 123.2(8) . . ? C14 C13 N12 107.1(9) . . ? C13 C14 N15 106.5(9) . . ? C11 N15 C14 112.6(8) . . ? C11 N15 C16 123.6(8) . . ? C14 N15 C16 122.7(8) . . ? C17 C16 C18 111.2(10) . . ? C17 C16 N15 108.1(8) . . ? C18 C16 N15 109.6(8) . . ? C17 C16 C19 111.0(10) . . ? C18 C16 C19 108.8(9) . . ? N15 C16 C19 108.2(9) . . ? N22 C21 N25 111.6(11) . . ? C21 N22 C23 104.9(9) . . ? C21 N22 Cu1 125.7(8) . . ? C23 N22 Cu1 128.0(7) . . ? C24 C23 N22 110.1(10) . . ? C23 C24 N25 106.5(10) . . ? C21 N25 C24 106.9(9) . . ? C21 N25 C26 127.3(9) . . ? C24 N25 C26 125.7(9) . . ? N25 C26 C29 109.6(9) . . ? N25 C26 C27 109.7(9) . . ? C29 C26 C27 110.0(11) . . ? N25 C26 C28 108.0(10) . . ? C29 C26 C28 111.1(10) . . ? C27 C26 C28 108.4(10) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 24.10 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 1.257 _refine_diff_density_min -0.773 _refine_diff_density_rms 0.155 #===END data_ivsh20 _database_code_depnum_ccdc_archive 'CCDC 697054' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 'in paper 7' _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H35 Br2 Cu2 N5' _chemical_formula_weight 632.43 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 9.65390(10) _cell_length_b 12.1517(2) _cell_length_c 22.0186(3) _cell_angle_alpha 90.00 _cell_angle_beta 98.9950(10) _cell_angle_gamma 90.00 _cell_volume 2551.26(6) _cell_formula_units_Z 4 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description polyhedron _exptl_crystal_colour colorless _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.647 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1272 _exptl_absorpt_coefficient_mu 4.815 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.4172 _exptl_absorpt_correction_T_max 0.5521 _exptl_absorpt_process_details 'Blessing, Acta Cryst. (1995) A51 33-38.' _exptl_special_details ; ? ; _diffrn_ambient_temperature 200(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 26001 _diffrn_reflns_av_R_equivalents 0.0485 _diffrn_reflns_av_sigmaI/netI 0.0436 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_theta_min 1.87 _diffrn_reflns_theta_max 27.50 _reflns_number_total 5858 _reflns_number_gt 4177 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0352P)^2^+1.3689P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5858 _refine_ls_number_parameters 297 _refine_ls_number_restraints 42 _refine_ls_R_factor_all 0.0616 _refine_ls_R_factor_gt 0.0336 _refine_ls_wR_factor_ref 0.0823 _refine_ls_wR_factor_gt 0.0734 _refine_ls_goodness_of_fit_ref 1.034 _refine_ls_restrained_S_all 1.043 _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 0.91436(4) 0.65676(3) 0.159571(18) 0.03133(11) Uani 1 1 d . . . Cu2 Cu 0.94425(4) 0.74905(3) 0.043791(19) 0.03377(12) Uani 1 1 d . . . Br1 Br 0.94096(4) 0.85693(3) 0.139288(16) 0.04041(11) Uani 1 1 d . . . Br2 Br 0.71311(4) 0.74343(3) -0.015565(15) 0.03419(10) Uani 1 1 d . . . C1 C 1.0705(3) 0.5607(2) 0.18262(13) 0.0249(7) Uani 1 1 d . . . N2 N 1.1238(3) 0.4948(2) 0.14157(11) 0.0255(6) Uani 1 1 d . . . C3 C 1.2274(4) 0.4263(3) 0.16953(15) 0.0330(8) Uani 1 1 d . . . H3 H 1.2789 0.3740 0.1500 0.040 Uiso 1 1 calc R . . C4 C 1.2415(4) 0.4477(3) 0.22979(14) 0.0330(8) Uani 1 1 d . . . H4 H 1.3045 0.4127 0.2614 0.040 Uiso 1 1 calc R . . N5 N 1.1466(3) 0.5307(2) 0.23740(11) 0.0246(6) Uani 1 1 d . . . C6 C 1.1330(4) 0.5765(3) 0.29967(14) 0.0314(8) Uani 1 1 d . . . C7 C 1.0395(4) 0.6762(3) 0.29376(15) 0.0377(8) Uani 1 1 d . . . H7A H 1.0759 0.7310 0.2677 0.056 Uiso 1 1 calc R . . H7B H 1.0374 0.7076 0.3346 0.056 Uiso 1 1 calc R . . H7C H 0.9444 0.6549 0.2752 0.056 Uiso 1 1 calc R . . C8 C 1.0702(6) 0.4866(4) 0.33519(19) 0.0722(15) Uani 1 1 d . . . H8A H 0.9819 0.4610 0.3112 0.108 Uiso 1 1 calc R . . H8B H 1.0521 0.5161 0.3746 0.108 Uiso 1 1 calc R . . H8C H 1.1360 0.4249 0.3426 0.108 Uiso 1 1 calc R . . C9 C 1.2790(4) 0.6077(4) 0.33152(18) 0.0571(12) Uani 1 1 d . . . H9A H 1.3388 0.5421 0.3362 0.086 Uiso 1 1 calc R . . H9B H 1.2730 0.6387 0.3721 0.086 Uiso 1 1 calc R . . H9C H 1.3194 0.6626 0.3067 0.086 Uiso 1 1 calc R . . C10 C 1.0795(3) 0.5008(3) 0.07550(13) 0.0278(7) Uani 1 1 d . . . H10A H 0.9795 0.5225 0.0671 0.033 Uiso 1 1 calc R . . H10B H 1.0880 0.4269 0.0575 0.033 Uiso 1 1 calc R . . C11 C 1.1157(3) 0.6824(3) 0.02828(13) 0.0276(7) Uani 1 1 d . . . N12 N 1.1614(3) 0.5787(2) 0.04572(11) 0.0245(6) Uani 1 1 d . . . C13 C 1.2918(3) 0.5576(3) 0.03013(15) 0.0339(8) Uani 1 1 d . . . H13 H 1.3446 0.4917 0.0376 0.041 Uiso 1 1 calc R . . C14 C 1.3291(3) 0.6487(3) 0.00229(15) 0.0368(8) Uani 1 1 d . . . H14 H 1.4139 0.6595 -0.0137 0.044 Uiso 1 1 calc R . . N15 N 1.2217(3) 0.7237(2) 0.00122(12) 0.0302(6) Uani 1 1 d . A . C16 C 1.2203(3) 0.8342(3) -0.03009(15) 0.0364(8) Uani 1 1 d DU . . C17 C 1.2029(17) 0.8142(8) -0.0973(3) 0.109(6) Uani 0.592(13) 1 d PDU A 1 H17A H 1.2770 0.7646 -0.1065 0.163 Uiso 0.592(13) 1 calc PR A 1 H17B H 1.2091 0.8843 -0.1188 0.163 Uiso 0.592(13) 1 calc PR A 1 H17C H 1.1111 0.7806 -0.1112 0.163 Uiso 0.592(13) 1 calc PR A 1 C18 C 1.3629(8) 0.8909(7) -0.0116(6) 0.078(4) Uani 0.592(13) 1 d PDU A 1 H18A H 1.3782 0.9055 0.0327 0.118 Uiso 0.592(13) 1 calc PR A 1 H18B H 1.3639 0.9606 -0.0340 0.118 Uiso 0.592(13) 1 calc PR A 1 H18C H 1.4376 0.8430 -0.0218 0.118 Uiso 0.592(13) 1 calc PR A 1 C19 C 1.1143(10) 0.9124(6) -0.0099(5) 0.079(5) Uani 0.592(13) 1 d PDU A 1 H19A H 1.1372 0.9250 0.0345 0.118 Uiso 0.592(13) 1 calc PR A 1 H19B H 1.0203 0.8804 -0.0195 0.118 Uiso 0.592(13) 1 calc PR A 1 H19C H 1.1168 0.9826 -0.0317 0.118 Uiso 0.592(13) 1 calc PR A 1 C17B C 1.261(2) 0.9112(9) 0.0183(5) 0.099(9) Uani 0.408(13) 1 d PDU A 2 H17D H 1.3557 0.8943 0.0389 0.148 Uiso 0.408(13) 1 calc PR A 2 H17E H 1.1952 0.9065 0.0481 0.148 Uiso 0.408(13) 1 calc PR A 2 H17F H 1.2583 0.9858 0.0013 0.148 Uiso 0.408(13) 1 calc PR A 2 C18B C 1.0741(9) 0.8484(12) -0.0663(7) 0.080(7) Uani 0.408(13) 1 d PDU A 2 H18D H 1.0583 0.7932 -0.0990 0.120 Uiso 0.408(13) 1 calc PR A 2 H18E H 1.0652 0.9222 -0.0844 0.120 Uiso 0.408(13) 1 calc PR A 2 H18F H 1.0045 0.8390 -0.0387 0.120 Uiso 0.408(13) 1 calc PR A 2 C19B C 1.3187(13) 0.8274(12) -0.0770(6) 0.070(5) Uani 0.408(13) 1 d PDU A 2 H19D H 1.2847 0.7715 -0.1079 0.104 Uiso 0.408(13) 1 calc PR A 2 H19E H 1.4127 0.8072 -0.0564 0.104 Uiso 0.408(13) 1 calc PR A 2 H19F H 1.3225 0.8989 -0.0972 0.104 Uiso 0.408(13) 1 calc PR A 2 N21 N 0.7039(3) 0.6398(3) 0.13265(14) 0.0363(7) Uani 1 1 d . . . H21 H 0.695(3) 0.652(3) 0.0948(16) 0.034(10) Uiso 1 1 d . . . C22 C 0.6144(4) 0.7222(3) 0.15602(19) 0.0502(10) Uani 1 1 d . . . H22A H 0.5167 0.7141 0.1348 0.060 Uiso 1 1 calc R . . H22B H 0.6472 0.7970 0.1476 0.060 Uiso 1 1 calc R . . C23 C 0.6191(4) 0.7074(4) 0.22434(19) 0.0534(11) Uani 1 1 d . . . H23A H 0.5561 0.7615 0.2396 0.064 Uiso 1 1 calc R . . H23B H 0.7156 0.7207 0.2458 0.064 Uiso 1 1 calc R . . C24 C 0.5737(5) 0.5917(4) 0.2381(2) 0.0653(13) Uani 1 1 d . . . H24A H 0.5864 0.5806 0.2831 0.078 Uiso 1 1 calc R . . H24B H 0.4729 0.5823 0.2217 0.078 Uiso 1 1 calc R . . C25 C 0.6578(5) 0.5066(3) 0.20958(19) 0.0600(12) Uani 1 1 d . . . H25A H 0.7565 0.5087 0.2302 0.072 Uiso 1 1 calc R . . H25B H 0.6200 0.4324 0.2158 0.072 Uiso 1 1 calc R . . C26 C 0.6523(4) 0.5273(3) 0.14211(18) 0.0529(11) Uani 1 1 d . . . H26A H 0.7112 0.4727 0.1246 0.064 Uiso 1 1 calc R . . H26B H 0.5547 0.5195 0.1207 0.064 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 0.0331(2) 0.0380(2) 0.0233(2) 0.00210(17) 0.00578(17) 0.00889(19) Cu2 0.0325(2) 0.0328(2) 0.0377(2) 0.00681(18) 0.01072(19) 0.00502(18) Br1 0.0607(3) 0.02774(19) 0.03219(19) -0.00307(15) 0.00543(17) -0.00670(17) Br2 0.03113(18) 0.0412(2) 0.02966(18) 0.00770(15) 0.00296(14) 0.00142(15) C1 0.0293(17) 0.0244(17) 0.0210(15) 0.0008(12) 0.0045(13) -0.0013(13) N2 0.0329(15) 0.0238(14) 0.0189(13) -0.0002(10) 0.0015(11) 0.0028(11) C3 0.042(2) 0.0275(18) 0.0285(17) 0.0006(14) 0.0018(15) 0.0121(15) C4 0.042(2) 0.0289(19) 0.0253(17) 0.0006(14) -0.0017(15) 0.0104(15) N5 0.0308(15) 0.0250(14) 0.0176(12) -0.0008(10) 0.0022(11) 0.0026(11) C6 0.040(2) 0.0351(19) 0.0183(15) -0.0031(13) 0.0033(14) 0.0042(15) C7 0.043(2) 0.044(2) 0.0251(17) -0.0086(15) 0.0048(16) 0.0090(17) C8 0.131(5) 0.050(3) 0.046(2) 0.010(2) 0.045(3) 0.000(3) C9 0.047(2) 0.075(3) 0.043(2) -0.032(2) -0.0111(19) 0.017(2) C10 0.0354(19) 0.0289(18) 0.0172(15) -0.0028(12) -0.0016(13) 0.0003(14) C11 0.0276(17) 0.0348(19) 0.0186(15) 0.0011(13) -0.0018(13) -0.0005(14) N12 0.0258(14) 0.0285(15) 0.0179(12) -0.0005(11) -0.0007(11) 0.0033(11) C13 0.0291(18) 0.040(2) 0.0314(18) 0.0021(15) 0.0012(15) 0.0121(16) C14 0.0278(18) 0.049(2) 0.0341(19) 0.0054(17) 0.0059(15) 0.0061(17) N15 0.0262(15) 0.0388(17) 0.0253(14) 0.0074(12) 0.0031(12) 0.0036(12) C16 0.038(2) 0.040(2) 0.0332(18) 0.0150(15) 0.0096(16) 0.0008(16) C17 0.22(2) 0.068(7) 0.033(4) 0.023(4) 0.005(6) 0.009(8) C18 0.062(5) 0.044(5) 0.128(10) 0.015(5) 0.009(5) -0.008(4) C19 0.082(7) 0.048(5) 0.120(10) 0.045(6) 0.059(8) 0.024(5) C17B 0.19(3) 0.039(7) 0.063(8) -0.001(5) 0.009(8) -0.042(11) C18B 0.034(5) 0.084(11) 0.115(14) 0.089(11) -0.009(6) -0.006(6) C19B 0.055(7) 0.087(10) 0.073(9) 0.047(8) 0.029(7) 0.022(7) N21 0.0318(16) 0.051(2) 0.0265(16) 0.0097(14) 0.0054(13) 0.0038(14) C22 0.037(2) 0.061(3) 0.056(3) 0.016(2) 0.0169(19) 0.0141(19) C23 0.042(2) 0.071(3) 0.049(2) -0.005(2) 0.014(2) 0.008(2) C24 0.065(3) 0.090(4) 0.045(3) 0.010(2) 0.023(2) -0.010(3) C25 0.075(3) 0.049(3) 0.056(3) 0.014(2) 0.011(2) -0.024(2) C26 0.049(2) 0.056(3) 0.053(2) -0.012(2) 0.004(2) -0.018(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 C1 1.912(3) . ? Cu1 N21 2.036(3) . ? Cu1 Br1 2.4936(6) . ? Cu1 Cu2 2.8408(6) . ? Cu2 C11 1.921(3) . ? Cu2 Br2 2.4042(5) . ? Cu2 Br1 2.4823(5) . ? C1 N5 1.360(4) . ? C1 N2 1.367(4) . ? N2 C3 1.371(4) . ? N2 C10 1.453(4) . ? C3 C4 1.338(4) . ? C4 N5 1.391(4) . ? N5 C6 1.504(4) . ? C6 C7 1.504(4) . ? C6 C9 1.522(5) . ? C6 C8 1.523(5) . ? C10 N12 1.453(4) . ? C11 N15 1.358(4) . ? C11 N12 1.370(4) . ? N12 C13 1.379(4) . ? C13 C14 1.342(5) . ? C14 N15 1.378(4) . ? N15 C16 1.508(4) . ? C16 C17B 1.427(9) . ? C16 C17 1.484(8) . ? C16 C19B 1.512(9) . ? C16 C19 1.514(7) . ? C16 C18B 1.518(8) . ? C16 C18 1.537(7) . ? N21 C22 1.467(5) . ? N21 C26 1.481(5) . ? C22 C23 1.509(6) . ? C23 C24 1.517(6) . ? C24 C25 1.511(6) . ? C25 C26 1.500(6) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 Cu1 N21 136.47(13) . . ? C1 Cu1 Br1 122.98(9) . . ? N21 Cu1 Br1 99.94(9) . . ? C1 Cu1 Cu2 107.03(9) . . ? N21 Cu1 Cu2 90.89(8) . . ? Br1 Cu1 Cu2 55.000(14) . . ? C11 Cu2 Br2 130.08(9) . . ? C11 Cu2 Br1 119.92(9) . . ? Br2 Cu2 Br1 109.98(2) . . ? C11 Cu2 Cu1 101.80(9) . . ? Br2 Cu2 Cu1 105.113(18) . . ? Br1 Cu2 Cu1 55.373(15) . . ? Cu2 Br1 Cu1 69.627(16) . . ? N5 C1 N2 102.9(2) . . ? N5 C1 Cu1 133.9(2) . . ? N2 C1 Cu1 123.0(2) . . ? C1 N2 C3 112.5(2) . . ? C1 N2 C10 123.4(3) . . ? C3 N2 C10 124.1(3) . . ? C4 C3 N2 106.4(3) . . ? C3 C4 N5 107.1(3) . . ? C1 N5 C4 111.2(2) . . ? C1 N5 C6 126.7(3) . . ? C4 N5 C6 122.1(2) . . ? N5 C6 C7 110.8(2) . . ? N5 C6 C9 107.8(3) . . ? C7 C6 C9 109.8(3) . . ? N5 C6 C8 107.6(3) . . ? C7 C6 C8 109.9(3) . . ? C9 C6 C8 110.9(3) . . ? N2 C10 N12 112.9(2) . . ? N15 C11 N12 103.4(3) . . ? N15 C11 Cu2 130.7(2) . . ? N12 C11 Cu2 125.9(2) . . ? C11 N12 C13 111.5(3) . . ? C11 N12 C10 123.5(3) . . ? C13 N12 C10 124.9(3) . . ? C14 C13 N12 106.3(3) . . ? C13 C14 N15 107.4(3) . . ? C11 N15 C14 111.4(3) . . ? C11 N15 C16 125.2(3) . . ? C14 N15 C16 123.3(3) . . ? C17B C16 C17 145.9(7) . . ? C17B C16 N15 105.1(5) . . ? C17 C16 N15 107.6(4) . . ? C17B C16 C19B 114.8(9) . . ? C17 C16 C19B 45.1(6) . . ? N15 C16 C19B 107.6(5) . . ? C17B C16 C19 59.0(8) . . ? C17 C16 C19 114.8(6) . . ? N15 C16 C19 112.5(4) . . ? C19B C16 C19 139.6(6) . . ? C17B C16 C18B 116.1(9) . . ? C17 C16 C18B 62.9(7) . . ? N15 C16 C18B 106.4(4) . . ? C19B C16 C18B 106.2(7) . . ? C19 C16 C18B 57.8(7) . . ? C17B C16 C18 51.7(7) . . ? C17 C16 C18 107.1(7) . . ? N15 C16 C18 109.6(4) . . ? C19B C16 C18 64.7(6) . . ? C19 C16 C18 105.0(6) . . ? C18B C16 C18 144.0(6) . . ? C22 N21 C26 110.5(3) . . ? C22 N21 Cu1 116.4(3) . . ? C26 N21 Cu1 113.3(2) . . ? N21 C22 C23 109.9(3) . . ? C22 C23 C24 110.2(4) . . ? C25 C24 C23 111.2(3) . . ? C26 C25 C24 111.0(4) . . ? N21 C26 C25 109.5(3) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.904 _refine_diff_density_min -0.752 _refine_diff_density_rms 0.088 #===END