# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2014 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_Compound_1a # data_d371jj _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C10 H12 Cu N2 O6' _chemical_formula_weight 319.76 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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z' '-x+1/2, y+1/2, -z' 'x+1/2, -y+1/2, -z' _cell_length_a 7.6423(4) _cell_length_b 24.3583(15) _cell_length_c 6.3921(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1189.91(12) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 9965 _cell_measurement_theta_min 2.79 _cell_measurement_theta_max 27.80 _exptl_crystal_description 'Thin plate' _exptl_crystal_colour green _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.09 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.785 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 652 _exptl_absorpt_coefficient_mu 1.861 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5250 _exptl_absorpt_correction_T_max 0.5633 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2008)' _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 '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 27749 _diffrn_reflns_av_R_equivalents 0.0487 _diffrn_reflns_av_sigmaI/netI 0.0286 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -31 _diffrn_reflns_limit_k_max 31 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 2.79 _diffrn_reflns_theta_max 27.50 _reflns_number_total 2726 _reflns_number_gt 2583 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0288P)^2^+0.7600P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.021(13) _refine_ls_number_reflns 2726 _refine_ls_number_parameters 183 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0297 _refine_ls_R_factor_gt 0.0265 _refine_ls_wR_factor_ref 0.0607 _refine_ls_wR_factor_gt 0.0598 _refine_ls_goodness_of_fit_ref 1.070 _refine_ls_restrained_S_all 1.071 _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 0.76463(3) 0.293907(11) 0.28102(4) 0.00975(8) Uani 1 1 d . . . O1 O 0.5378(2) 0.31864(7) 0.3669(3) 0.0150(4) Uani 1 1 d . . . O2 O 1.0117(2) 0.28164(7) 0.2230(3) 0.0120(3) Uani 1 1 d . . . O3 O 1.1953(2) 0.28027(7) -0.0474(3) 0.0156(4) Uani 1 1 d . . . O4 O 0.7744(2) 0.24496(7) 0.5171(3) 0.0147(4) Uani 1 1 d D . . H4A H 0.688(3) 0.2385(12) 0.594(4) 0.018 Uiso 1 1 d D . . H4B H 0.858(3) 0.2232(10) 0.532(5) 0.018 Uiso 1 1 d D . . O5 O 0.2137(3) 0.52194(8) -0.0786(4) 0.0323(5) Uani 1 1 d . . . O6 O 0.1484(3) 0.54138(8) 0.2434(4) 0.0378(6) Uani 1 1 d . . . C1 C 0.4659(3) 0.36514(9) 0.3024(4) 0.0140(5) Uani 1 1 d . . . C2 C 0.3588(3) 0.39468(11) 0.4415(5) 0.0197(6) Uani 1 1 d . . . H2 H 0.3429 0.3815 0.5800 0.024 Uiso 1 1 calc R . . C3 C 0.2764(4) 0.44242(11) 0.3809(5) 0.0233(6) Uani 1 1 d . . . H3 H 0.2060 0.4624 0.4769 0.028 Uiso 1 1 calc R . . C4 C 0.2979(3) 0.46076(10) 0.1785(5) 0.0211(6) Uani 1 1 d . . . C5 C 0.4051(3) 0.43309(11) 0.0370(5) 0.0175(6) Uani 1 1 d . . . H6 H 0.4194 0.4469 -0.1010 0.021 Uiso 1 1 calc R . . C6 C 0.4907(3) 0.38560(10) 0.0969(4) 0.0129(5) Uani 1 1 d . . . C7 C 0.6093(3) 0.35578(11) -0.0536(4) 0.0140(5) Uani 1 1 d . . . H7A H 0.5558 0.3203 -0.0935 0.017 Uiso 1 1 calc R . . H7B H 0.6246 0.3780 -0.1820 0.017 Uiso 1 1 calc R . . N1 N 0.7820(3) 0.34599(8) 0.0457(3) 0.0104(4) Uani 1 1 d . . . H1 H 0.810(4) 0.3744(15) 0.085(5) 0.034(10) Uiso 1 1 d . . . C8 C 0.9150(3) 0.32243(10) -0.0974(4) 0.0120(5) Uani 1 1 d . . . H8 H 0.8544 0.2934 -0.1811 0.014 Uiso 1 1 calc R . . C9 C 1.0543(3) 0.29330(11) 0.0321(4) 0.0111(4) Uani 1 1 d . . . C10 C 0.9902(3) 0.36327(10) -0.2533(4) 0.0196(6) Uani 1 1 d . . . H11A H 0.8945 0.3809 -0.3300 0.029 Uiso 1 1 calc R . . H11B H 1.0666 0.3440 -0.3520 0.029 Uiso 1 1 calc R . . H11C H 1.0578 0.3912 -0.1784 0.029 Uiso 1 1 calc R . . N2 N 0.2143(3) 0.51082(9) 0.1091(4) 0.0266(6) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.00665(12) 0.01094(13) 0.01165(13) 0.00215(11) 0.00097(10) 0.00089(11) O1 0.0102(8) 0.0134(9) 0.0212(9) 0.0061(8) 0.0053(7) 0.0026(7) O2 0.0109(7) 0.0137(8) 0.0113(8) 0.0024(7) 0.0000(7) 0.0022(6) O3 0.0126(8) 0.0158(9) 0.0184(9) -0.0014(7) 0.0049(7) 0.0038(7) O4 0.0111(8) 0.0201(9) 0.0128(8) 0.0064(7) 0.0026(8) 0.0051(8) O5 0.0218(10) 0.0191(10) 0.0558(15) 0.0105(10) -0.0088(11) 0.0038(9) O6 0.0294(10) 0.0152(10) 0.0688(17) 0.0079(11) 0.0261(12) 0.0083(8) C1 0.0088(10) 0.0095(12) 0.0236(13) 0.0012(10) 0.0008(10) -0.0019(8) C2 0.0136(12) 0.0203(15) 0.0250(14) 0.0018(12) 0.0046(11) 0.0001(10) C3 0.0128(12) 0.0159(13) 0.0411(16) -0.0014(11) 0.0104(13) 0.0018(11) C4 0.0098(11) 0.0098(12) 0.0438(18) 0.0028(11) 0.0024(11) 0.0023(9) C5 0.0114(12) 0.0141(14) 0.0269(15) 0.0043(11) -0.0001(11) -0.0024(10) C6 0.0092(11) 0.0093(12) 0.0203(13) 0.0007(10) -0.0022(10) -0.0005(9) C7 0.0105(11) 0.0130(13) 0.0185(13) 0.0041(11) -0.0028(10) 0.0013(10) N1 0.0104(10) 0.0083(10) 0.0125(10) -0.0021(7) -0.0012(9) 0.0004(8) C8 0.0123(11) 0.0106(12) 0.0130(13) 0.0012(10) 0.0026(10) 0.0006(9) C9 0.0116(10) 0.0083(11) 0.0133(11) -0.0039(10) 0.0015(8) -0.0028(10) C10 0.0185(11) 0.0210(14) 0.0193(15) 0.0053(11) 0.0062(11) 0.0052(10) N2 0.0113(10) 0.0130(12) 0.0556(17) 0.0061(11) 0.0038(11) 0.0000(9) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 O1 1.9153(17) . ? Cu1 O4 1.9247(16) . ? Cu1 O2 1.9472(15) . ? Cu1 N1 1.972(2) . ? Cu1 O3 2.4034(17) 4_455 ? O1 C1 1.325(3) . ? O2 C9 1.295(3) . ? O3 C9 1.233(3) . ? O3 Cu1 2.4034(17) 4 ? O4 H4A 0.838(10) . ? O4 H4B 0.836(10) . ? O5 N2 1.230(3) . ? O6 N2 1.243(3) . ? C1 C2 1.406(4) . ? C1 C6 1.417(4) . ? C2 C3 1.378(4) . ? C2 H2 0.9500 . ? C3 C4 1.378(4) . ? C3 H3 0.9500 . ? C4 C5 1.394(4) . ? C4 N2 1.446(3) . ? C5 C6 1.383(4) . ? C5 H6 0.9500 . ? C6 C7 1.508(3) . ? C7 N1 1.484(3) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? N1 C8 1.483(3) . ? N1 H1 0.77(4) . ? C8 C10 1.521(3) . ? C8 C9 1.524(3) . ? C8 H8 1.0000 . ? C10 H11A 0.9800 . ? C10 H11B 0.9800 . ? C10 H11C 0.9800 . ? 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 O1 Cu1 O4 90.28(8) . . ? O1 Cu1 O2 168.60(7) . . ? O4 Cu1 O2 90.96(7) . . ? O1 Cu1 N1 94.43(8) . . ? O4 Cu1 N1 173.66(9) . . ? O2 Cu1 N1 83.58(8) . . ? O1 Cu1 O3 102.44(7) . 4_455 ? O4 Cu1 O3 91.73(7) . 4_455 ? O2 Cu1 O3 88.85(6) . 4_455 ? N1 Cu1 O3 91.41(8) . 4_455 ? C1 O1 Cu1 123.71(15) . . ? C9 O2 Cu1 112.96(14) . . ? C9 O3 Cu1 129.95(16) . 4 ? Cu1 O4 H4A 123(2) . . ? Cu1 O4 H4B 121(2) . . ? H4A O4 H4B 115(3) . . ? O1 C1 C2 118.8(2) . . ? O1 C1 C6 122.3(2) . . ? C2 C1 C6 118.9(2) . . ? C3 C2 C1 121.3(3) . . ? C3 C2 H2 119.3 . . ? C1 C2 H2 119.3 . . ? C2 C3 C4 118.9(3) . . ? C2 C3 H3 120.6 . . ? C4 C3 H3 120.6 . . ? C3 C4 C5 121.5(2) . . ? C3 C4 N2 120.6(3) . . ? C5 C4 N2 117.9(3) . . ? C6 C5 C4 120.2(3) . . ? C6 C5 H6 119.9 . . ? C4 C5 H6 119.9 . . ? C5 C6 C1 119.2(2) . . ? C5 C6 C7 120.7(2) . . ? C1 C6 C7 120.1(2) . . ? N1 C7 C6 109.8(2) . . ? N1 C7 H7A 109.7 . . ? C6 C7 H7A 109.7 . . ? N1 C7 H7B 109.7 . . ? C6 C7 H7B 109.7 . . ? H7A C7 H7B 108.2 . . ? C8 N1 C7 114.09(19) . . ? C8 N1 Cu1 105.51(15) . . ? C7 N1 Cu1 111.70(15) . . ? C8 N1 H1 111(3) . . ? C7 N1 H1 104(3) . . ? Cu1 N1 H1 111(3) . . ? N1 C8 C10 114.2(2) . . ? N1 C8 C9 108.92(19) . . ? C10 C8 C9 113.4(2) . . ? N1 C8 H8 106.6 . . ? C10 C8 H8 106.6 . . ? C9 C8 H8 106.6 . . ? O3 C9 O2 123.5(2) . . ? O3 C9 C8 120.5(2) . . ? O2 C9 C8 115.98(19) . . ? C8 C10 H11A 109.5 . . ? C8 C10 H11B 109.5 . . ? H11A C10 H11B 109.5 . . ? C8 C10 H11C 109.5 . . ? H11A C10 H11C 109.5 . . ? H11B C10 H11C 109.5 . . ? O5 N2 O6 122.7(2) . . ? O5 N2 C4 119.1(3) . . ? O6 N2 C4 118.2(3) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O4 Cu1 O1 C1 161.1(2) . . . . ? O2 Cu1 O1 C1 64.8(5) . . . . ? N1 Cu1 O1 C1 -14.6(2) . . . . ? O3 Cu1 O1 C1 -107.04(19) 4_455 . . . ? O1 Cu1 O2 C9 -104.9(4) . . . . ? O4 Cu1 O2 C9 158.86(16) . . . . ? N1 Cu1 O2 C9 -24.40(16) . . . . ? O3 Cu1 O2 C9 67.15(16) 4_455 . . . ? Cu1 O1 C1 C2 -145.60(19) . . . . ? Cu1 O1 C1 C6 35.5(3) . . . . ? O1 C1 C2 C3 -178.0(2) . . . . ? C6 C1 C2 C3 0.9(4) . . . . ? C1 C2 C3 C4 1.1(4) . . . . ? C2 C3 C4 C5 -2.1(4) . . . . ? C2 C3 C4 N2 -179.7(2) . . . . ? C3 C4 C5 C6 1.1(4) . . . . ? N2 C4 C5 C6 178.7(2) . . . . ? C4 C5 C6 C1 0.9(4) . . . . ? C4 C5 C6 C7 -179.0(2) . . . . ? O1 C1 C6 C5 177.0(2) . . . . ? C2 C1 C6 C5 -1.9(3) . . . . ? O1 C1 C6 C7 -3.0(3) . . . . ? C2 C1 C6 C7 178.1(2) . . . . ? C5 C6 C7 N1 128.2(2) . . . . ? C1 C6 C7 N1 -51.7(3) . . . . ? C6 C7 N1 C8 -173.5(2) . . . . ? C6 C7 N1 Cu1 66.9(2) . . . . ? O1 Cu1 N1 C8 -159.23(15) . . . . ? O4 Cu1 N1 C8 62.9(8) . . . . ? O2 Cu1 N1 C8 32.04(15) . . . . ? O3 Cu1 N1 C8 -56.64(15) 4_455 . . . ? O1 Cu1 N1 C7 -34.74(17) . . . . ? O4 Cu1 N1 C7 -172.6(7) . . . . ? O2 Cu1 N1 C7 156.53(17) . . . . ? O3 Cu1 N1 C7 67.85(16) 4_455 . . . ? C7 N1 C8 C10 74.9(3) . . . . ? Cu1 N1 C8 C10 -162.11(17) . . . . ? C7 N1 C8 C9 -157.2(2) . . . . ? Cu1 N1 C8 C9 -34.2(2) . . . . ? Cu1 O3 C9 O2 101.0(2) 4 . . . ? Cu1 O3 C9 C8 -76.1(3) 4 . . . ? Cu1 O2 C9 O3 -167.71(19) . . . . ? Cu1 O2 C9 C8 9.5(3) . . . . ? N1 C8 C9 O3 -165.2(2) . . . . ? C10 C8 C9 O3 -36.9(3) . . . . ? N1 C8 C9 O2 17.5(3) . . . . ? C10 C8 C9 O2 145.8(2) . . . . ? C3 C4 N2 O5 -169.2(2) . . . . ? C5 C4 N2 O5 13.1(4) . . . . ? C3 C4 N2 O6 12.0(4) . . . . ? C5 C4 N2 O6 -165.7(2) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O4 H4A O2 0.838(10) 1.851(11) 2.685(2) 174(3) 4_456 O4 H4B O1 0.836(10) 1.829(13) 2.647(2) 166(3) 4_556 N1 H1 O6 0.77(4) 2.31(4) 3.067(3) 169(3) 2_665 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.352 _refine_diff_density_min -0.365 _refine_diff_density_rms 0.067 _database_code_depnum_ccdc_archive 'CCDC 965509' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_compound_3a # data_d382jj _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H30 Cu2 N2 O10' _chemical_formula_weight 609.56 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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 13.8398(15) _cell_length_b 7.2308(8) _cell_length_c 13.9096(16) _cell_angle_alpha 90.00 _cell_angle_beta 118.406(3) _cell_angle_gamma 90.00 _cell_volume 1224.4(2) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 9792 _cell_measurement_theta_min 2.94 _cell_measurement_theta_max 28.28 _exptl_crystal_description Block _exptl_crystal_colour green _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.653 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 628 _exptl_absorpt_coefficient_mu 1.796 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6623 _exptl_absorpt_correction_T_max 0.9235 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2008)' _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-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 54610 _diffrn_reflns_av_R_equivalents 0.0455 _diffrn_reflns_av_sigmaI/netI 0.0274 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.87 _diffrn_reflns_theta_max 27.49 _reflns_number_total 5623 _reflns_number_gt 5230 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0295P)^2^+0.1557P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.007(8) _refine_ls_number_reflns 5623 _refine_ls_number_parameters 348 _refine_ls_number_restraints 6 _refine_ls_R_factor_all 0.0279 _refine_ls_R_factor_gt 0.0230 _refine_ls_wR_factor_ref 0.0541 _refine_ls_wR_factor_gt 0.0527 _refine_ls_goodness_of_fit_ref 1.067 _refine_ls_restrained_S_all 1.067 _refine_ls_shift/su_max 0.002 _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 0.365833(17) 0.51421(3) 0.523478(16) 0.01168(6) Uani 1 1 d . . . Cu2 Cu 0.127813(16) 0.49554(3) 0.453980(16) 0.01269(7) Uani 1 1 d . . . O1 O 0.26896(10) 0.4506(2) 0.58326(10) 0.0126(3) Uani 1 1 d . . . C1 C 0.30341(15) 0.4618(3) 0.69240(14) 0.0106(4) Uani 1 1 d . . . C2 C 0.23379(15) 0.5271(3) 0.73163(14) 0.0120(4) Uani 1 1 d . . . H2A H 0.1624 0.5697 0.6813 0.014 Uiso 1 1 calc R . . C3 C 0.26691(15) 0.5307(3) 0.84256(14) 0.0130(4) Uani 1 1 d . . . H3 H 0.2181 0.5740 0.8677 0.016 Uiso 1 1 calc R . . C4 C 0.37141(15) 0.4712(3) 0.91687(14) 0.0123(4) Uani 1 1 d . . . C5 C 0.44248(16) 0.4083(3) 0.87990(15) 0.0110(4) Uani 1 1 d . . . H5 H 0.5143 0.3688 0.9310 0.013 Uiso 1 1 calc R . . C6 C 0.40930(16) 0.4026(3) 0.76763(15) 0.0108(4) Uani 1 1 d . . . C7 C 0.48365(16) 0.3127(3) 0.73081(15) 0.0123(4) Uani 1 1 d . . . H7C H 0.5564 0.2938 0.7955 0.015 Uiso 1 1 calc R . . H7D H 0.4536 0.1891 0.7010 0.015 Uiso 1 1 calc R . . N1 N 0.49961(14) 0.4154(3) 0.64766(13) 0.0111(3) Uani 1 1 d . . . H1 H 0.5257(18) 0.340(4) 0.6191(18) 0.020(6) Uiso 1 1 d . . . C8 C 0.57642(16) 0.5752(3) 0.68261(15) 0.0134(4) Uani 1 1 d . . . H8 H 0.5467 0.6717 0.7129 0.016 Uiso 1 1 calc R . . C9 C 0.56765(15) 0.6505(3) 0.57451(15) 0.0121(4) Uani 1 1 d . . . C10 C 0.69412(16) 0.5352(3) 0.76807(15) 0.0172(5) Uani 1 1 d . . . H10A H 0.6950 0.4858 0.8341 0.026 Uiso 1 1 calc R . . H10B H 0.7371 0.6497 0.7861 0.026 Uiso 1 1 calc R . . H10C H 0.7262 0.4442 0.7392 0.026 Uiso 1 1 calc R . . O2 O 0.47333(11) 0.6336(2) 0.48970(11) 0.0137(3) Uani 1 1 d . . . O3 O 0.64742(11) 0.7222(2) 0.57310(12) 0.0178(3) Uani 1 1 d . . . O4 O 0.22613(11) 0.5876(2) 0.40078(10) 0.0121(3) Uani 1 1 d . . . C11 C 0.19448(16) 0.5996(3) 0.29232(15) 0.0108(4) Uani 1 1 d . . . C12 C 0.26488(16) 0.5492(3) 0.25096(15) 0.0125(4) Uani 1 1 d . . . H12 H 0.3369 0.5074 0.2997 0.015 Uiso 1 1 calc R . . C13 C 0.23167(16) 0.5590(3) 0.14014(16) 0.0137(4) Uani 1 1 d . . . H14 H 0.2807 0.5239 0.1135 0.016 Uiso 1 1 calc R . . C14 C 0.12598(16) 0.6204(3) 0.06763(15) 0.0136(4) Uani 1 1 d . . . C15 C 0.05572(17) 0.6729(3) 0.10772(16) 0.0128(4) Uani 1 1 d . . . H15 H -0.0159 0.7161 0.0586 0.015 Uiso 1 1 calc R . . C16 C 0.08867(16) 0.6632(3) 0.21920(15) 0.0109(4) Uani 1 1 d . . . C17 C 0.00935(16) 0.7147(3) 0.26010(16) 0.0127(4) Uani 1 1 d . . . H17A H 0.0389 0.8198 0.3117 0.015 Uiso 1 1 calc R . . H17B H -0.0616 0.7530 0.1980 0.015 Uiso 1 1 calc R . . N2 N -0.00750(14) 0.5520(2) 0.31626(13) 0.0119(4) Uani 1 1 d . . . H2 H -0.0200(18) 0.457(3) 0.2755(17) 0.014 Uiso 1 1 d . . . C18 C -0.09989(15) 0.5718(3) 0.34165(15) 0.0118(4) Uani 1 1 d . . . H18 H -0.1009 0.7041 0.3621 0.014 Uiso 1 1 calc R . . C19 C -0.07382(15) 0.4571(3) 0.44268(16) 0.0129(4) Uani 1 1 d . . . C20 C -0.21113(15) 0.5320(3) 0.24504(15) 0.0167(5) Uani 1 1 d . . . H20A H -0.2243 0.6176 0.1854 0.025 Uiso 1 1 calc R . . H20B H -0.2684 0.5482 0.2668 0.025 Uiso 1 1 calc R . . H20C H -0.2127 0.4045 0.2204 0.025 Uiso 1 1 calc R . . O5 O 0.02800(11) 0.4224(2) 0.50674(11) 0.0174(3) Uani 1 1 d . . . O6 O -0.14719(11) 0.4092(2) 0.46440(11) 0.0185(3) Uani 1 1 d . . . O7 O 0.37171(13) 0.8648(2) 0.60559(12) 0.0214(4) Uani 1 1 d D . . H7A H 0.3067(10) 0.874(4) 0.5960(19) 0.026 Uiso 1 1 d D . . H7B H 0.3710(18) 0.948(3) 0.5631(16) 0.026 Uiso 1 1 d D . . O8 O 0.13388(12) 0.1918(2) 0.38421(12) 0.0162(3) Uani 1 1 d D . . H8A H 0.1348(17) 0.111(3) 0.4276(16) 0.019 Uiso 1 1 d D . . H8B H 0.1989(10) 0.193(3) 0.3937(19) 0.019 Uiso 1 1 d D . . O9 O 0.39772(11) 0.4818(2) 1.02586(9) 0.0175(3) Uani 1 1 d . . . O10 O 0.09962(12) 0.6213(2) -0.04094(11) 0.0214(4) Uani 1 1 d . . . C21 C 0.50233(18) 0.4142(3) 1.10316(16) 0.0203(5) Uani 1 1 d . . . H21A H 0.5082 0.2831 1.0889 0.030 Uiso 1 1 calc R . . H21B H 0.5113 0.4286 1.1770 0.030 Uiso 1 1 calc R . . H21C H 0.5597 0.4843 1.0970 0.030 Uiso 1 1 calc R . . C22 C -0.01197(17) 0.6596(3) -0.11756(16) 0.0201(5) Uani 1 1 d . . . H22A H -0.0600 0.5706 -0.1077 0.030 Uiso 1 1 calc R . . H22B H -0.0220 0.6492 -0.1920 0.030 Uiso 1 1 calc R . . H22C H -0.0307 0.7852 -0.1057 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 0.00660(11) 0.01959(14) 0.00808(10) 0.00283(13) 0.00286(8) -0.00055(11) Cu2 0.00683(11) 0.02206(15) 0.00883(10) 0.00429(13) 0.00345(8) 0.00054(12) O1 0.0078(6) 0.0236(9) 0.0068(6) 0.0017(5) 0.0038(5) 0.0002(6) C1 0.0122(9) 0.0091(10) 0.0099(8) 0.0002(7) 0.0048(7) -0.0020(7) C2 0.0098(8) 0.0123(11) 0.0129(8) 0.0010(9) 0.0047(7) 0.0014(8) C3 0.0148(9) 0.0130(11) 0.0142(8) -0.0016(8) 0.0093(7) -0.0006(8) C4 0.0169(9) 0.0118(11) 0.0098(8) -0.0019(8) 0.0077(7) -0.0031(8) C5 0.0096(9) 0.0103(10) 0.0104(9) 0.0014(7) 0.0025(7) -0.0001(8) C6 0.0111(10) 0.0115(10) 0.0108(9) 0.0006(7) 0.0059(8) -0.0001(8) C7 0.0102(10) 0.0176(11) 0.0092(9) 0.0019(8) 0.0046(8) 0.0011(8) N1 0.0107(8) 0.0138(9) 0.0108(8) -0.0002(7) 0.0069(7) 0.0001(7) C8 0.0124(10) 0.0145(10) 0.0129(9) -0.0006(7) 0.0056(8) 0.0000(8) C9 0.0102(10) 0.0126(10) 0.0126(10) -0.0008(8) 0.0047(8) 0.0026(8) C10 0.0127(9) 0.0175(12) 0.0155(9) 0.0028(9) 0.0020(7) -0.0011(8) O2 0.0088(7) 0.0209(8) 0.0106(7) 0.0018(6) 0.0039(6) -0.0023(6) O3 0.0098(7) 0.0233(9) 0.0200(8) 0.0054(6) 0.0068(6) -0.0021(6) O4 0.0076(7) 0.0201(8) 0.0087(6) 0.0008(6) 0.0040(5) -0.0002(6) C11 0.0118(9) 0.0110(10) 0.0087(9) 0.0008(7) 0.0041(8) -0.0029(8) C12 0.0107(9) 0.0135(12) 0.0128(9) 0.0002(7) 0.0052(7) -0.0010(7) C13 0.0143(10) 0.0150(11) 0.0150(9) -0.0008(7) 0.0097(8) -0.0009(7) C14 0.0152(10) 0.0168(11) 0.0082(9) 0.0003(8) 0.0051(8) -0.0028(8) C15 0.0121(10) 0.0120(10) 0.0108(9) 0.0024(8) 0.0027(8) -0.0016(8) C16 0.0100(9) 0.0105(10) 0.0118(9) 0.0014(8) 0.0047(8) -0.0002(8) C17 0.0131(11) 0.0133(11) 0.0106(9) 0.0025(8) 0.0048(8) 0.0013(8) N2 0.0101(8) 0.0143(10) 0.0114(8) -0.0001(7) 0.0053(7) -0.0007(6) C18 0.0065(9) 0.0126(10) 0.0147(9) -0.0007(7) 0.0038(8) 0.0010(7) C19 0.0108(9) 0.0151(11) 0.0140(9) -0.0038(8) 0.0069(7) -0.0018(8) C20 0.0114(9) 0.0188(13) 0.0165(9) 0.0019(9) 0.0040(7) -0.0005(8) O5 0.0106(7) 0.0271(8) 0.0142(7) 0.0061(6) 0.0057(6) 0.0012(6) O6 0.0116(7) 0.0300(9) 0.0153(7) -0.0002(6) 0.0074(6) -0.0030(6) O7 0.0142(8) 0.0290(10) 0.0211(8) 0.0019(7) 0.0086(7) 0.0026(7) O8 0.0148(8) 0.0195(8) 0.0149(7) 0.0013(6) 0.0075(6) 0.0005(6) O9 0.0175(7) 0.0270(9) 0.0083(6) -0.0019(7) 0.0062(5) 0.0031(7) O10 0.0181(7) 0.0370(10) 0.0088(7) 0.0006(7) 0.0063(6) 0.0020(7) C21 0.0257(12) 0.0213(12) 0.0104(10) 0.0012(8) 0.0058(9) 0.0069(10) C22 0.0236(12) 0.0225(12) 0.0078(9) 0.0007(9) 0.0022(9) 0.0032(10) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 O1 1.9394(13) . ? Cu1 O4 1.9475(13) . ? Cu1 O2 1.9609(14) . ? Cu1 N1 1.9696(17) . ? Cu1 O7 2.7655(18) . ? Cu1 Cu2 2.9621(4) . ? Cu2 O5 1.9211(14) . ? Cu2 O4 1.9493(14) . ? Cu2 O1 1.9527(13) . ? Cu2 N2 1.9825(16) . ? Cu2 O8 2.4186(16) . ? O1 C1 1.360(2) . ? C1 C2 1.396(3) . ? C1 C6 1.402(3) . ? C2 C3 1.385(2) . ? C2 H2A 0.9500 . ? C3 C4 1.387(3) . ? C3 H3 0.9500 . ? C4 O9 1.383(2) . ? C4 C5 1.386(3) . ? C5 C6 1.403(3) . ? C5 H5 0.9500 . ? C6 C7 1.498(3) . ? C7 N1 1.477(2) . ? C7 H7C 0.9900 . ? C7 H7D 0.9900 . ? N1 C8 1.487(3) . ? N1 H1 0.85(2) . ? C8 C10 1.519(3) . ? C8 C9 1.549(3) . ? C8 H8 1.0000 . ? C9 O3 1.228(2) . ? C9 O2 1.283(2) . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? O4 C11 1.359(2) . ? C11 C12 1.395(3) . ? C11 C16 1.405(3) . ? C12 C13 1.385(3) . ? C12 H12 0.9500 . ? C13 C14 1.397(3) . ? C13 H14 0.9500 . ? C14 O10 1.375(2) . ? C14 C15 1.384(3) . ? C15 C16 1.395(3) . ? C15 H15 0.9500 . ? C16 C17 1.504(3) . ? C17 N2 1.490(3) . ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? N2 C18 1.487(2) . ? N2 H2 0.86(2) . ? C18 C20 1.513(2) . ? C18 C19 1.520(3) . ? C18 H18 1.0000 . ? C19 O6 1.239(2) . ? C19 O5 1.284(2) . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 0.9800 . ? O7 H7A 0.848(9) . ? O7 H7B 0.842(10) . ? O8 H8A 0.834(9) . ? O8 H8B 0.844(9) . ? O9 C21 1.418(2) . ? O10 C22 1.425(2) . ? C21 H21A 0.9800 . ? C21 H21B 0.9800 . ? C21 H21C 0.9800 . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C22 H22C 0.9800 . ? 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 O1 Cu1 O4 80.78(6) . . ? O1 Cu1 O2 164.86(6) . . ? O4 Cu1 O2 102.72(6) . . ? O1 Cu1 N1 95.22(6) . . ? O4 Cu1 N1 173.99(7) . . ? O2 Cu1 N1 82.30(6) . . ? O1 Cu1 O7 86.04(6) . . ? O4 Cu1 O7 86.23(6) . . ? O2 Cu1 O7 79.56(6) . . ? N1 Cu1 O7 98.03(6) . . ? O1 Cu1 Cu2 40.61(4) . . ? O4 Cu1 Cu2 40.54(4) . . ? O2 Cu1 Cu2 142.62(4) . . ? N1 Cu1 Cu2 134.84(5) . . ? O7 Cu1 Cu2 89.21(3) . . ? O5 Cu2 O4 176.00(7) . . ? O5 Cu2 O1 100.87(6) . . ? O4 Cu2 O1 80.40(6) . . ? O5 Cu2 N2 84.58(6) . . ? O4 Cu2 N2 94.12(6) . . ? O1 Cu2 N2 174.52(6) . . ? O5 Cu2 O8 94.13(6) . . ? O4 Cu2 O8 89.65(6) . . ? O1 Cu2 O8 90.45(6) . . ? N2 Cu2 O8 89.80(6) . . ? O5 Cu2 Cu1 141.08(4) . . ? O4 Cu2 Cu1 40.50(4) . . ? O1 Cu2 Cu1 40.28(4) . . ? N2 Cu2 Cu1 134.31(5) . . ? O8 Cu2 Cu1 85.81(4) . . ? C1 O1 Cu1 121.17(11) . . ? C1 O1 Cu2 133.15(12) . . ? Cu1 O1 Cu2 99.11(6) . . ? O1 C1 C2 121.05(16) . . ? O1 C1 C6 120.11(17) . . ? C2 C1 C6 118.81(16) . . ? C3 C2 C1 121.18(17) . . ? C3 C2 H2A 119.4 . . ? C1 C2 H2A 119.4 . . ? C2 C3 C4 119.96(17) . . ? C2 C3 H3 120.0 . . ? C4 C3 H3 120.0 . . ? O9 C4 C5 124.20(17) . . ? O9 C4 C3 115.93(16) . . ? C5 C4 C3 119.86(17) . . ? C4 C5 C6 120.56(18) . . ? C4 C5 H5 119.7 . . ? C6 C5 H5 119.7 . . ? C1 C6 C5 119.60(18) . . ? C1 C6 C7 121.41(17) . . ? C5 C6 C7 118.61(17) . . ? N1 C7 C6 115.61(17) . . ? N1 C7 H7C 108.4 . . ? C6 C7 H7C 108.4 . . ? N1 C7 H7D 108.4 . . ? C6 C7 H7D 108.4 . . ? H7C C7 H7D 107.4 . . ? C7 N1 C8 119.01(16) . . ? C7 N1 Cu1 116.16(12) . . ? C8 N1 Cu1 103.44(12) . . ? C7 N1 H1 107.4(17) . . ? C8 N1 H1 104.8(16) . . ? Cu1 N1 H1 104.7(15) . . ? N1 C8 C10 116.20(17) . . ? N1 C8 C9 104.02(15) . . ? C10 C8 C9 112.73(17) . . ? N1 C8 H8 107.8 . . ? C10 C8 H8 107.8 . . ? C9 C8 H8 107.8 . . ? O3 C9 O2 123.68(18) . . ? O3 C9 C8 120.54(17) . . ? O2 C9 C8 115.78(17) . . ? C8 C10 H10A 109.5 . . ? C8 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C8 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C9 O2 Cu1 112.19(12) . . ? C11 O4 Cu1 130.66(12) . . ? C11 O4 Cu2 121.92(12) . . ? Cu1 O4 Cu2 98.96(6) . . ? O4 C11 C12 121.44(17) . . ? O4 C11 C16 119.94(17) . . ? C12 C11 C16 118.62(17) . . ? C13 C12 C11 121.23(18) . . ? C13 C12 H12 119.4 . . ? C11 C12 H12 119.4 . . ? C12 C13 C14 119.94(18) . . ? C12 C13 H14 120.0 . . ? C14 C13 H14 120.0 . . ? O10 C14 C15 124.83(18) . . ? O10 C14 C13 115.74(18) . . ? C15 C14 C13 119.43(18) . . ? C14 C15 C16 120.89(18) . . ? C14 C15 H15 119.6 . . ? C16 C15 H15 119.6 . . ? C15 C16 C11 119.88(18) . . ? C15 C16 C17 119.79(17) . . ? C11 C16 C17 120.29(17) . . ? N2 C17 C16 109.12(16) . . ? N2 C17 H17A 109.9 . . ? C16 C17 H17A 109.9 . . ? N2 C17 H17B 109.9 . . ? C16 C17 H17B 109.9 . . ? H17A C17 H17B 108.3 . . ? C18 N2 C17 114.56(16) . . ? C18 N2 Cu2 108.30(11) . . ? C17 N2 Cu2 110.96(13) . . ? C18 N2 H2 108.0(15) . . ? C17 N2 H2 108.7(15) . . ? Cu2 N2 H2 106.0(15) . . ? N2 C18 C20 113.42(16) . . ? N2 C18 C19 108.34(15) . . ? C20 C18 C19 114.29(16) . . ? N2 C18 H18 106.8 . . ? C20 C18 H18 106.8 . . ? C19 C18 H18 106.8 . . ? O6 C19 O5 122.17(18) . . ? O6 C19 C18 121.10(17) . . ? O5 C19 C18 116.61(16) . . ? C18 C20 H20A 109.5 . . ? C18 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C18 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C19 O5 Cu2 115.62(12) . . ? Cu1 O7 H7A 100.9(18) . . ? Cu1 O7 H7B 112.3(17) . . ? H7A O7 H7B 100.1(19) . . ? Cu2 O8 H8A 109.6(17) . . ? Cu2 O8 H8B 99.7(17) . . ? H8A O8 H8B 104.0(19) . . ? C4 O9 C21 116.97(15) . . ? C14 O10 C22 116.70(16) . . ? O9 C21 H21A 109.5 . . ? O9 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? O9 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? O10 C22 H22A 109.5 . . ? O10 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? O10 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O7 H7A O6 0.848(9) 1.969(11) 2.798(2) 166(2) 2_556 N1 H1 O2 0.85(2) 2.13(3) 2.936(2) 158(2) 2_646 O8 H8B O3 0.844(9) 1.963(10) 2.802(2) 173(2) 2_646 O8 H8A O6 0.834(9) 2.043(10) 2.877(2) 176(2) 2_546 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.433 _refine_diff_density_min -0.217 _refine_diff_density_rms 0.065 _database_code_depnum_ccdc_archive 'CCDC 965510' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_Compound_4a # data_152 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H24 Cl2 Cu2 N2 O8' _chemical_formula_weight 618.39 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 13.1237(9) _cell_length_b 7.2533(5) _cell_length_c 13.6424(10) _cell_angle_alpha 90.00 _cell_angle_beta 117.0420(10) _cell_angle_gamma 90.00 _cell_volume 1156.65(14) _cell_formula_units_Z 2 _cell_measurement_temperature 223(2) _cell_measurement_reflns_used 3269 _cell_measurement_theta_min 2.06 _cell_measurement_theta_max 25.0 _exptl_crystal_description 'thin plates, cut' _exptl_crystal_colour green _exptl_crystal_size_max 0.16 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.776 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 628 _exptl_absorpt_coefficient_mu 2.120 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7279 _exptl_absorpt_correction_T_max 0.9588 _exptl_absorpt_process_details 'sadabs (Sheldrick, 1996)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 223(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 ? _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7300 _diffrn_reflns_av_R_equivalents 0.0281 _diffrn_reflns_av_sigmaI/netI 0.0847 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.74 _diffrn_reflns_theta_max 29.09 _reflns_number_total 5214 _reflns_number_gt 3986 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker AXS, SMART' _computing_cell_refinement 'Bruker AXS, SAINT' _computing_data_reduction 'Bruker AXS, SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker AXS, SHELXTL' _computing_publication_material 'Bruker AXS, 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^)+(0.0370P)^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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.029(18) _refine_ls_number_reflns 5214 _refine_ls_number_parameters 322 _refine_ls_number_restraints 13 _refine_ls_R_factor_all 0.0774 _refine_ls_R_factor_gt 0.0514 _refine_ls_wR_factor_ref 0.1001 _refine_ls_wR_factor_gt 0.0906 _refine_ls_goodness_of_fit_ref 1.006 _refine_ls_restrained_S_all 1.005 _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 0.36926(5) 0.44057(9) 0.34092(5) 0.0281(2) Uani 1 1 d D . . Cu2 Cu 0.12457(5) 0.47498(9) 0.17374(5) 0.02449(18) Uani 1 1 d D . . O1 O 0.2792(3) 0.5105(6) 0.1874(3) 0.0224(9) Uani 1 1 d . . . C1 C 0.3230(4) 0.5098(7) 0.1138(4) 0.0194(12) Uani 1 1 d . . . C2 C 0.2539(4) 0.4595(8) 0.0043(4) 0.0231(11) Uani 1 1 d . . . H2A H 0.1791 0.4172 -0.0169 0.028 Uiso 1 1 calc R . . C3 C 0.2943(4) 0.4711(9) -0.0736(4) 0.0242(12) Uani 1 1 d . . . H3 H 0.2467 0.4401 -0.1474 0.029 Uiso 1 1 calc R . . C4 C 0.4065(5) 0.5295(8) -0.0406(4) 0.0222(13) Uani 1 1 d . . . C5 C 0.4771(5) 0.5734(7) 0.0680(4) 0.0201(12) Uani 1 1 d . . . H5 H 0.5530 0.6094 0.0890 0.024 Uiso 1 1 calc R . . C6 C 0.4370(4) 0.5652(8) 0.1477(4) 0.0195(12) Uani 1 1 d . . . C7 C 0.5114(5) 0.6410(9) 0.2597(4) 0.0276(14) Uani 1 1 d . . . H7C H 0.5896 0.6496 0.2683 0.033 Uiso 1 1 calc R . . H7D H 0.4858 0.7670 0.2625 0.033 Uiso 1 1 calc R . . N1 N 0.5161(4) 0.5403(7) 0.3550(4) 0.0287(11) Uani 1 1 d . . . H1 H 0.5395 0.6252 0.4112 0.034 Uiso 1 1 calc R . . C8 C 0.5962(4) 0.3797(8) 0.4008(4) 0.0262(13) Uani 1 1 d . . . H8 H 0.5715 0.2820 0.3439 0.031 Uiso 1 1 calc R . . C9 C 0.5740(5) 0.3105(8) 0.4972(5) 0.0232(12) Uani 1 1 d . . . C10 C 0.7208(4) 0.4217(9) 0.4352(5) 0.0346(16) Uani 1 1 d . . . H10A H 0.7303 0.4545 0.3709 0.052 Uiso 1 1 calc R . . H10B H 0.7668 0.3138 0.4700 0.052 Uiso 1 1 calc R . . H10C H 0.7453 0.5237 0.4868 0.052 Uiso 1 1 calc R . . O2 O 0.4702(3) 0.3246(6) 0.4818(3) 0.0273(10) Uani 1 1 d . . . O3 O 0.6525(3) 0.2449(6) 0.5810(3) 0.0361(11) Uani 1 1 d . . . Cl1 Cl 0.45724(13) 0.5581(2) -0.13831(11) 0.0330(4) Uani 1 1 d . . . O4 O 0.2167(3) 0.3804(6) 0.3227(3) 0.0223(9) Uani 1 1 d . . . C11 C 0.1757(5) 0.3649(8) 0.3978(4) 0.0193(12) Uani 1 1 d . . . C12 C 0.2445(5) 0.4097(8) 0.5090(4) 0.0211(12) Uani 1 1 d . . . H12 H 0.3195 0.4519 0.5315 0.025 Uiso 1 1 calc R . . C13 C 0.2037(5) 0.3928(8) 0.5863(4) 0.0229(13) Uani 1 1 d . . . H13 H 0.2504 0.4233 0.6604 0.027 Uiso 1 1 calc R . . C14 C 0.0924(5) 0.3299(8) 0.5521(4) 0.0226(13) Uani 1 1 d . . . C15 C 0.0222(5) 0.2882(7) 0.4428(4) 0.0211(12) Uani 1 1 d . . . H15 H -0.0532 0.2486 0.4209 0.025 Uiso 1 1 calc R . . C16 C 0.0631(4) 0.3049(8) 0.3649(4) 0.0195(12) Uani 1 1 d . . . C17 C -0.0148(5) 0.2626(8) 0.2460(4) 0.0222(13) Uani 1 1 d . . . H17A H 0.0150 0.1565 0.2226 0.027 Uiso 1 1 calc R . . H17B H -0.0911 0.2309 0.2372 0.027 Uiso 1 1 calc R . . N2 N -0.0229(3) 0.4258(6) 0.1758(3) 0.0194(10) Uani 1 1 d . . . H2 H -0.0393 0.5269 0.2070 0.023 Uiso 1 1 calc R . . C18 C -0.1141(4) 0.4118(7) 0.0605(4) 0.0223(12) Uani 1 1 d . . . H18 H -0.1168 0.2809 0.0390 0.027 Uiso 1 1 calc R . . C19 C -0.0766(5) 0.5223(8) -0.0138(4) 0.0238(13) Uani 1 1 d . . . C20 C -0.2329(4) 0.4593(10) 0.0459(5) 0.0330(14) Uani 1 1 d . . . H20D H -0.2886 0.4363 -0.0297 0.050 Uiso 1 1 calc R . . H20E H -0.2353 0.5884 0.0633 0.050 Uiso 1 1 calc R . . H20F H -0.2505 0.3836 0.0948 0.050 Uiso 1 1 calc R . . O5 O 0.0306(3) 0.5510(6) 0.0243(3) 0.0289(10) Uani 1 1 d . . . O6 O -0.1471(3) 0.5701(6) -0.1073(3) 0.0326(10) Uani 1 1 d . . . Cl2 Cl 0.03736(13) 0.3096(2) 0.64743(12) 0.0306(4) Uani 1 1 d . . . O7 O 0.3787(4) 0.0953(7) 0.2666(4) 0.0446(13) Uani 1 1 d D . . H7A H 0.310(2) 0.103(5) 0.208(2) 0.070(11) Uiso 1 1 d D . . H7B H 0.365(4) 0.037(4) 0.317(3) 0.070(11) Uiso 1 1 d D . . O8 O 0.1241(3) 0.7801(6) 0.2456(3) 0.0286(10) Uani 1 1 d D . . H8A H 0.123(5) 0.875(3) 0.202(2) 0.070(11) Uiso 1 1 d D . . H8B H 0.187(3) 0.808(4) 0.309(3) 0.070(11) Uiso 1 1 d D . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.0128(4) 0.0531(6) 0.0188(3) 0.0118(4) 0.0075(3) 0.0024(3) Cu2 0.0131(3) 0.0433(5) 0.0171(3) 0.0080(3) 0.0069(3) -0.0014(3) O1 0.0134(19) 0.039(3) 0.0157(18) 0.0025(18) 0.0070(17) -0.0008(18) C1 0.019(3) 0.019(3) 0.022(3) 0.006(2) 0.012(2) 0.005(2) C2 0.016(3) 0.032(3) 0.022(2) 0.000(3) 0.010(2) 0.002(3) C3 0.024(3) 0.029(3) 0.018(2) -0.003(3) 0.008(2) 0.003(3) C4 0.028(3) 0.024(3) 0.023(3) 0.004(2) 0.019(3) 0.005(2) C5 0.018(3) 0.021(3) 0.023(3) 0.002(2) 0.011(3) 0.000(2) C6 0.016(3) 0.026(3) 0.018(3) 0.003(2) 0.010(2) 0.005(2) C7 0.021(3) 0.041(4) 0.019(3) 0.003(3) 0.008(3) -0.001(3) N1 0.023(2) 0.036(3) 0.029(3) 0.002(2) 0.014(2) 0.006(2) C8 0.024(3) 0.032(3) 0.030(3) -0.004(3) 0.019(3) 0.000(2) C9 0.020(3) 0.024(3) 0.025(3) 0.001(2) 0.010(3) 0.000(2) C10 0.018(3) 0.043(4) 0.041(3) 0.002(3) 0.013(3) 0.002(3) O2 0.017(2) 0.046(3) 0.017(2) 0.0091(19) 0.0053(19) -0.0002(18) O3 0.018(2) 0.054(3) 0.030(2) 0.012(2) 0.0046(19) 0.0047(19) Cl1 0.0350(8) 0.0483(10) 0.0249(7) -0.0016(7) 0.0218(7) -0.0027(7) O4 0.014(2) 0.041(2) 0.0138(18) 0.0050(17) 0.0076(18) 0.0001(17) C11 0.021(3) 0.022(3) 0.016(3) 0.002(2) 0.009(3) 0.002(2) C12 0.019(3) 0.025(3) 0.021(3) 0.004(2) 0.010(2) 0.000(2) C13 0.025(3) 0.029(3) 0.018(3) 0.001(2) 0.012(3) -0.002(2) C14 0.027(3) 0.027(3) 0.017(3) 0.000(2) 0.013(3) 0.004(2) C15 0.019(3) 0.018(3) 0.031(3) 0.007(2) 0.016(3) 0.000(2) C16 0.015(3) 0.028(3) 0.016(3) 0.006(2) 0.008(2) 0.001(2) C17 0.020(3) 0.031(3) 0.019(3) 0.000(3) 0.012(3) -0.003(3) N2 0.014(2) 0.026(3) 0.019(2) 0.002(2) 0.0082(18) 0.0014(19) C18 0.018(3) 0.024(3) 0.024(3) -0.001(2) 0.009(2) 0.004(2) C19 0.022(3) 0.026(3) 0.018(3) -0.002(2) 0.005(2) 0.008(2) C20 0.016(3) 0.046(4) 0.036(3) 0.009(4) 0.011(3) 0.000(3) O5 0.014(2) 0.053(3) 0.019(2) 0.008(2) 0.0073(18) 0.0003(19) O6 0.0178(19) 0.057(3) 0.017(2) 0.0063(19) 0.0032(17) 0.0070(19) Cl2 0.0365(9) 0.0390(9) 0.0279(8) 0.0019(7) 0.0247(8) -0.0012(7) O7 0.027(2) 0.075(4) 0.026(2) 0.002(2) 0.007(2) -0.001(2) O8 0.024(2) 0.036(3) 0.025(2) -0.0004(19) 0.010(2) -0.0052(19) _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 O1 1.947(3) . ? Cu1 O4 1.951(3) . ? Cu1 O2 1.960(4) . ? Cu1 N1 1.983(4) . ? Cu1 Cu2 2.9861(7) . ? Cu2 O5 1.922(4) . ? Cu2 O4 1.956(4) . ? Cu2 O1 1.969(3) . ? Cu2 N2 1.981(4) . ? Cu2 O8 2.421(4) . ? O1 C1 1.364(5) . ? C1 C2 1.398(7) . ? C1 C6 1.409(7) . ? C2 C3 1.389(6) . ? C3 C4 1.396(7) . ? C4 C5 1.381(7) . ? C4 Cl1 1.752(5) . ? C5 C6 1.407(6) . ? C6 C7 1.495(7) . ? C7 N1 1.469(7) . ? N1 C8 1.502(7) . ? C8 C10 1.513(7) . ? C8 C9 1.555(7) . ? C9 O3 1.234(6) . ? C9 O2 1.285(6) . ? O4 C11 1.362(6) . ? C11 C16 1.405(7) . ? C11 C12 1.406(7) . ? C12 C13 1.388(6) . ? C13 C14 1.393(8) . ? C14 C15 1.384(7) . ? C14 Cl2 1.757(5) . ? C15 C16 1.395(7) . ? C16 C17 1.504(7) . ? C17 N2 1.496(7) . ? N2 C18 1.485(6) . ? C18 C20 1.518(6) . ? C18 C19 1.538(7) . ? C19 O6 1.237(6) . ? C19 O5 1.277(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 O1 Cu1 O4 80.53(14) . . ? O1 Cu1 O2 167.37(17) . . ? O4 Cu1 O2 103.06(15) . . ? O1 Cu1 N1 95.57(16) . . ? O4 Cu1 N1 171.44(18) . . ? O2 Cu1 N1 82.40(18) . . ? O1 Cu1 Cu2 40.59(9) . . ? O4 Cu1 Cu2 40.23(10) . . ? O2 Cu1 Cu2 142.89(11) . . ? N1 Cu1 Cu2 134.71(14) . . ? O5 Cu2 O4 176.09(18) . . ? O5 Cu2 O1 101.48(15) . . ? O4 Cu2 O1 79.86(15) . . ? O5 Cu2 N2 84.68(16) . . ? O4 Cu2 N2 93.93(15) . . ? O1 Cu2 N2 173.77(16) . . ? O5 Cu2 O8 92.79(17) . . ? O4 Cu2 O8 90.82(16) . . ? O1 Cu2 O8 91.97(15) . . ? N2 Cu2 O8 88.65(16) . . ? O5 Cu2 Cu1 141.49(11) . . ? O4 Cu2 Cu1 40.10(10) . . ? O1 Cu2 Cu1 40.05(10) . . ? N2 Cu2 Cu1 133.82(12) . . ? O8 Cu2 Cu1 88.11(10) . . ? C1 O1 Cu1 122.6(3) . . ? C1 O1 Cu2 133.7(3) . . ? Cu1 O1 Cu2 99.36(14) . . ? O1 C1 C2 120.1(4) . . ? O1 C1 C6 119.8(5) . . ? C2 C1 C6 120.1(4) . . ? C3 C2 C1 120.9(5) . . ? C2 C3 C4 119.1(5) . . ? C5 C4 C3 120.7(4) . . ? C5 C4 Cl1 119.2(4) . . ? C3 C4 Cl1 120.1(4) . . ? C4 C5 C6 121.0(5) . . ? C5 C6 C1 118.2(5) . . ? C5 C6 C7 118.3(5) . . ? C1 C6 C7 122.9(4) . . ? N1 C7 C6 117.8(5) . . ? C7 N1 C8 119.5(4) . . ? C7 N1 Cu1 116.6(4) . . ? C8 N1 Cu1 102.9(3) . . ? N1 C8 C10 115.3(5) . . ? N1 C8 C9 103.7(4) . . ? C10 C8 C9 113.2(5) . . ? O3 C9 O2 124.1(5) . . ? O3 C9 C8 120.6(5) . . ? O2 C9 C8 115.4(5) . . ? C9 O2 Cu1 112.9(3) . . ? C11 O4 Cu1 131.0(3) . . ? C11 O4 Cu2 122.8(3) . . ? Cu1 O4 Cu2 99.67(15) . . ? O4 C11 C16 120.2(5) . . ? O4 C11 C12 121.0(5) . . ? C16 C11 C12 118.8(5) . . ? C13 C12 C11 121.3(5) . . ? C12 C13 C14 118.8(5) . . ? C15 C14 C13 121.0(5) . . ? C15 C14 Cl2 118.9(4) . . ? C13 C14 Cl2 120.0(4) . . ? C14 C15 C16 120.2(5) . . ? C15 C16 C11 119.8(5) . . ? C15 C16 C17 119.7(5) . . ? C11 C16 C17 120.5(4) . . ? N2 C17 C16 110.2(4) . . ? C18 N2 C17 114.4(4) . . ? C18 N2 Cu2 108.6(3) . . ? C17 N2 Cu2 111.5(3) . . ? N2 C18 C20 114.1(4) . . ? N2 C18 C19 108.5(4) . . ? C20 C18 C19 114.3(4) . . ? O6 C19 O5 122.9(5) . . ? O6 C19 C18 120.8(5) . . ? O5 C19 C18 116.1(4) . . ? C19 O5 Cu2 116.2(3) . . ? _diffrn_measured_fraction_theta_max 0.916 _diffrn_reflns_theta_full 29.09 _diffrn_measured_fraction_theta_full 0.916 _refine_diff_density_max 0.773 _refine_diff_density_min -0.675 _refine_diff_density_rms 0.098 _database_code_depnum_ccdc_archive 'CCDC 965511' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_Compound_5a # data_d380 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H24 Br2 Cu2 N2 O8' _chemical_formula_weight 707.31 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' O O 0.0106 0.0060 '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) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 13.1442(16) _cell_length_b 7.2517(9) _cell_length_c 13.7162(17) _cell_angle_alpha 90.00 _cell_angle_beta 117.640(4) _cell_angle_gamma 90.00 _cell_volume 1158.2(2) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 9567 _cell_measurement_theta_min 2.81 _cell_measurement_theta_max 31.82 _exptl_crystal_description Rod _exptl_crystal_colour green _exptl_crystal_size_max 0.48 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 2.028 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 700 _exptl_absorpt_coefficient_mu 5.337 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.3838 _exptl_absorpt_correction_T_max 0.8563 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2008)' _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 '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 51200 _diffrn_reflns_av_R_equivalents 0.0293 _diffrn_reflns_av_sigmaI/netI 0.0193 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.93 _diffrn_reflns_theta_max 27.50 _reflns_number_total 5269 _reflns_number_gt 5126 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0350P)^2^+1.1687P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.028(7) _refine_ls_number_reflns 5269 _refine_ls_number_parameters 327 _refine_ls_number_restraints 8 _refine_ls_R_factor_all 0.0230 _refine_ls_R_factor_gt 0.0219 _refine_ls_wR_factor_ref 0.0571 _refine_ls_wR_factor_gt 0.0565 _refine_ls_goodness_of_fit_ref 1.014 _refine_ls_restrained_S_all 1.013 _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 0.62469(3) 0.59774(5) 0.17327(3) 0.01280(8) Uani 1 1 d . . . Cu2 Cu 0.86991(3) 0.56733(5) 0.34298(3) 0.01673(9) Uani 1 1 d . . . Br1 Br 0.53145(2) 0.42730(4) 0.64834(2) 0.01438(7) Uani 1 1 d . . . Br2 Br 0.96095(2) 0.69328(4) -0.14025(2) 0.01591(7) Uani 1 1 d . . . O1 O 0.71754(16) 0.5039(3) 0.32231(16) 0.0130(4) Uani 1 1 d . . . C1 C 0.6772(2) 0.4878(4) 0.3967(2) 0.0121(5) Uani 1 1 d . . . C2 C 0.7451(2) 0.5326(4) 0.5069(2) 0.0141(6) Uani 1 1 d . . . H2A H 0.8213 0.5758 0.5308 0.017 Uiso 1 1 calc R . . C3 C 0.7026(2) 0.5147(4) 0.5828(2) 0.0138(5) Uani 1 1 d . . . H3 H 0.7491 0.5467 0.6578 0.017 Uiso 1 1 calc R . . C4 C 0.5921(2) 0.4500(4) 0.5475(2) 0.0128(5) Uani 1 1 d . . . C5 C 0.5229(2) 0.4071(4) 0.4382(2) 0.0126(5) Uani 1 1 d . . . H5 H 0.4466 0.3653 0.4151 0.015 Uiso 1 1 calc R . . C6 C 0.5638(2) 0.4244(4) 0.3615(2) 0.0115(5) Uani 1 1 d . . . C7 C 0.4872(2) 0.3787(4) 0.2428(2) 0.0122(5) Uani 1 1 d . . . H7C H 0.5196 0.2735 0.2204 0.015 Uiso 1 1 calc R . . H7D H 0.4102 0.3429 0.2326 0.015 Uiso 1 1 calc R . . N1 N 0.47737(19) 0.5433(3) 0.17324(19) 0.0109(4) Uani 1 1 d . . . H1 H 0.467(3) 0.641(5) 0.199(3) 0.013 Uiso 1 1 d . . . C8 C 0.3860(2) 0.5274(4) 0.0579(2) 0.0121(5) Uani 1 1 d . . . H8 H 0.3826 0.3951 0.0361 0.014 Uiso 1 1 calc R . . C9 C 0.4235(2) 0.6388(4) -0.0150(2) 0.0148(6) Uani 1 1 d . . . C10 C 0.2678(2) 0.5786(5) 0.0434(2) 0.0175(6) Uani 1 1 d . . . H10A H 0.2494 0.5022 0.0921 0.026 Uiso 1 1 calc R . . H10B H 0.2105 0.5576 -0.0332 0.026 Uiso 1 1 calc R . . H10C H 0.2671 0.7089 0.0620 0.026 Uiso 1 1 calc R . . O2 O 0.53049(16) 0.6710(3) 0.02339(16) 0.0177(4) Uani 1 1 d . . . O3 O 0.35128(16) 0.6834(3) -0.10965(16) 0.0189(4) Uani 1 1 d . . . O4 O 0.77907(16) 0.6331(3) 0.18877(16) 0.0139(4) Uani 1 1 d . . . C11 C 0.8226(2) 0.6329(4) 0.1173(2) 0.0114(5) Uani 1 1 d . . . C12 C 0.7547(2) 0.5795(4) 0.0079(2) 0.0128(5) Uani 1 1 d . . . H12 H 0.6796 0.5331 -0.0143 0.015 Uiso 1 1 calc R . . C13 C 0.7957(2) 0.5934(4) -0.0688(2) 0.0137(5) Uani 1 1 d . . . H13 H 0.7481 0.5596 -0.1433 0.016 Uiso 1 1 calc R . . C14 C 0.9060(2) 0.6565(4) -0.0362(2) 0.0122(5) Uani 1 1 d . . . C15 C 0.9766(2) 0.7031(4) 0.0730(2) 0.0119(5) Uani 1 1 d . . . H15 H 1.0530 0.7428 0.0950 0.014 Uiso 1 1 calc R . . C16 C 0.9360(2) 0.6919(4) 0.1504(2) 0.0122(5) Uani 1 1 d . . . C17 C 1.0104(2) 0.7706(5) 0.2643(2) 0.0163(6) Uani 1 1 d . . . H17A H 1.0895 0.7837 0.2739 0.020 Uiso 1 1 calc R . . H17B H 0.9821 0.8960 0.2669 0.020 Uiso 1 1 calc R . . N2 N 1.01627(19) 0.6664(4) 0.35794(19) 0.0158(5) Uani 1 1 d . . . H2 H 1.050(3) 0.747(5) 0.424(3) 0.019 Uiso 1 1 d . . . C18 C 1.0956(2) 0.5065(4) 0.4015(2) 0.0162(6) Uani 1 1 d . . . H18 H 1.0693 0.4093 0.3432 0.019 Uiso 1 1 calc R . . C19 C 1.0747(2) 0.4347(4) 0.4972(2) 0.0145(5) Uani 1 1 d . . . C20 C 1.2211(3) 0.5462(5) 0.4366(3) 0.0217(7) Uani 1 1 d . . . H20A H 1.2299 0.5840 0.3723 0.033 Uiso 1 1 calc R . . H20B H 1.2666 0.4349 0.4688 0.033 Uiso 1 1 calc R . . H20C H 1.2478 0.6455 0.4913 0.033 Uiso 1 1 calc R . . O5 O 0.97170(16) 0.4489(3) 0.48307(16) 0.0167(4) Uani 1 1 d . . . O6 O 1.15361(18) 0.3665(3) 0.57977(18) 0.0229(5) Uani 1 1 d . . . O7 O 0.62431(18) 0.8993(3) 0.24385(17) 0.0171(4) Uani 1 1 d D . . H7A H 0.677(2) 0.910(5) 0.300(2) 0.021 Uiso 1 1 d D . . H7B H 0.631(3) 0.986(4) 0.214(3) 0.021 Uiso 1 1 d D . . O8 O 0.8795(2) 0.2254(4) 0.2680(2) 0.0260(6) Uani 1 1 d D . . H8A H 0.872(3) 0.146(5) 0.303(3) 0.031 Uiso 1 1 d D . . H8B H 0.817(2) 0.222(6) 0.219(3) 0.031 Uiso 1 1 d D . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.00677(15) 0.02214(18) 0.00900(15) 0.00420(13) 0.00323(12) -0.00020(13) Cu2 0.00784(16) 0.0302(2) 0.01161(16) 0.00725(15) 0.00405(14) 0.00055(14) Br1 0.01745(14) 0.01642(13) 0.01331(13) 0.00115(11) 0.01054(11) -0.00071(11) Br2 0.01749(14) 0.02097(14) 0.01278(13) -0.00059(11) 0.00999(11) -0.00170(11) O1 0.0081(9) 0.0212(10) 0.0112(9) 0.0011(8) 0.0056(8) -0.0008(8) C1 0.0122(13) 0.0118(12) 0.0146(13) 0.0031(11) 0.0082(11) 0.0033(10) C2 0.0121(13) 0.0145(14) 0.0152(13) 0.0011(11) 0.0058(11) -0.0008(10) C3 0.0145(13) 0.0162(14) 0.0101(12) 0.0019(11) 0.0052(11) 0.0026(11) C4 0.0144(13) 0.0124(13) 0.0133(13) 0.0022(10) 0.0080(11) 0.0025(10) C5 0.0108(12) 0.0122(13) 0.0149(13) 0.0004(11) 0.0060(11) -0.0015(10) C6 0.0132(12) 0.0103(11) 0.0108(12) -0.0001(11) 0.0053(10) 0.0001(11) C7 0.0130(13) 0.0135(13) 0.0105(12) 0.0006(10) 0.0059(11) -0.0015(10) N1 0.0090(10) 0.0122(12) 0.0105(11) 0.0000(9) 0.0039(9) 0.0009(8) C8 0.0096(12) 0.0141(13) 0.0091(12) -0.0004(10) 0.0015(10) -0.0006(10) C9 0.0132(12) 0.0181(14) 0.0137(13) -0.0031(11) 0.0069(11) 0.0015(10) C10 0.0095(12) 0.0214(15) 0.0202(14) 0.0050(12) 0.0057(11) 0.0023(11) O2 0.0113(10) 0.0285(11) 0.0132(10) 0.0037(10) 0.0055(8) -0.0014(9) O3 0.0117(9) 0.0321(12) 0.0101(9) 0.0039(9) 0.0028(8) 0.0036(9) O4 0.0071(8) 0.0247(11) 0.0098(9) 0.0031(8) 0.0037(7) 0.0012(8) C11 0.0091(12) 0.0121(13) 0.0119(13) 0.0039(10) 0.0040(10) 0.0020(9) C12 0.0112(12) 0.0130(13) 0.0161(13) 0.0011(11) 0.0079(11) 0.0000(10) C13 0.0150(13) 0.0137(13) 0.0132(12) -0.0007(11) 0.0072(11) -0.0004(11) C14 0.0166(13) 0.0115(13) 0.0121(12) 0.0009(10) 0.0097(11) 0.0025(10) C15 0.0105(12) 0.0123(13) 0.0130(12) 0.0014(11) 0.0056(11) 0.0000(10) C16 0.0101(12) 0.0141(12) 0.0124(12) 0.0026(11) 0.0052(10) 0.0007(11) C17 0.0129(13) 0.0229(15) 0.0132(13) 0.0013(12) 0.0061(11) -0.0020(11) N2 0.0131(11) 0.0204(13) 0.0134(11) -0.0008(10) 0.0058(9) -0.0009(10) C18 0.0130(13) 0.0186(14) 0.0202(14) -0.0030(12) 0.0104(12) -0.0024(12) C19 0.0133(12) 0.0141(12) 0.0145(13) 0.0016(11) 0.0052(11) 0.0006(11) C20 0.0122(14) 0.0227(16) 0.0295(17) 0.0043(13) 0.0091(13) 0.0007(11) O5 0.0106(10) 0.0275(12) 0.0110(10) 0.0071(9) 0.0041(8) 0.0036(9) O6 0.0133(10) 0.0274(12) 0.0211(11) 0.0067(9) 0.0022(9) 0.0011(9) O7 0.0141(10) 0.0233(12) 0.0128(10) -0.0005(9) 0.0052(8) -0.0017(9) O8 0.0162(11) 0.0385(16) 0.0202(12) -0.0019(10) 0.0057(10) -0.0011(10) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 O2 1.918(2) . ? Cu1 O1 1.954(2) . ? Cu1 O4 1.9566(19) . ? Cu1 N1 1.976(2) . ? Cu1 O7 2.392(2) . ? Cu1 Cu2 2.9824(5) . ? Cu2 O1 1.9431(19) . ? Cu2 O4 1.9452(19) . ? Cu2 O5 1.958(2) . ? Cu2 N2 1.973(2) . ? Br1 C4 1.897(3) . ? Br2 C14 1.893(3) . ? O1 C1 1.356(3) . ? C1 C2 1.391(4) . ? C1 C6 1.414(4) . ? C2 C3 1.397(4) . ? C2 H2A 0.9500 . ? C3 C4 1.383(4) . ? C3 H3 0.9500 . ? C4 C5 1.380(4) . ? C5 C6 1.391(4) . ? C5 H5 0.9500 . ? C6 C7 1.501(4) . ? C7 N1 1.496(3) . ? C7 H7C 0.9900 . ? C7 H7D 0.9900 . ? N1 C8 1.482(3) . ? N1 H1 0.83(4) . ? C8 C10 1.518(4) . ? C8 C9 1.534(4) . ? C8 H8 1.0000 . ? C9 O3 1.244(3) . ? C9 O2 1.273(3) . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? O4 C11 1.345(3) . ? C11 C12 1.398(4) . ? C11 C16 1.408(4) . ? C12 C13 1.391(4) . ? C12 H12 0.9500 . ? C13 C14 1.382(4) . ? C13 H13 0.9500 . ? C14 C15 1.389(4) . ? C15 C16 1.394(4) . ? C15 H15 0.9500 . ? C16 C17 1.518(4) . ? C17 N2 1.461(4) . ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? N2 C18 1.487(4) . ? N2 H2 0.99(4) . ? C18 C20 1.516(4) . ? C18 C19 1.549(4) . ? C18 H18 1.0000 . ? C19 O6 1.230(4) . ? C19 O5 1.280(3) . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 0.9800 . ? O7 H7A 0.77(2) . ? O7 H7B 0.78(2) . ? O8 H8A 0.79(2) . ? O8 H8B 0.79(2) . ? 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 O2 Cu1 O1 175.69(10) . . ? O2 Cu1 O4 101.62(8) . . ? O1 Cu1 O4 79.57(8) . . ? O2 Cu1 N1 84.83(9) . . ? O1 Cu1 N1 93.85(9) . . ? O4 Cu1 N1 173.22(9) . . ? O2 Cu1 O7 93.38(9) . . ? O1 Cu1 O7 90.71(8) . . ? O4 Cu1 O7 91.89(8) . . ? N1 Cu1 O7 89.81(9) . . ? O2 Cu1 Cu2 141.58(6) . . ? O1 Cu1 Cu2 39.93(6) . . ? O4 Cu1 Cu2 40.01(6) . . ? N1 Cu1 Cu2 133.59(7) . . ? O7 Cu1 Cu2 87.48(5) . . ? O1 Cu2 O4 80.11(8) . . ? O1 Cu2 O5 103.19(9) . . ? O4 Cu2 O5 165.88(9) . . ? O1 Cu2 N2 172.11(10) . . ? O4 Cu2 N2 95.78(9) . . ? O5 Cu2 N2 82.43(9) . . ? O1 Cu2 Cu1 40.19(6) . . ? O4 Cu2 Cu1 40.29(6) . . ? O5 Cu2 Cu1 142.88(6) . . ? N2 Cu2 Cu1 134.65(7) . . ? C1 O1 Cu2 130.32(17) . . ? C1 O1 Cu1 123.03(16) . . ? Cu2 O1 Cu1 99.88(9) . . ? O1 C1 C2 121.3(2) . . ? O1 C1 C6 119.3(2) . . ? C2 C1 C6 119.4(2) . . ? C1 C2 C3 120.7(3) . . ? C1 C2 H2A 119.6 . . ? C3 C2 H2A 119.6 . . ? C4 C3 C2 119.3(3) . . ? C4 C3 H3 120.4 . . ? C2 C3 H3 120.4 . . ? C5 C4 C3 120.8(3) . . ? C5 C4 Br1 119.0(2) . . ? C3 C4 Br1 120.2(2) . . ? C4 C5 C6 120.6(2) . . ? C4 C5 H5 119.7 . . ? C6 C5 H5 119.7 . . ? C5 C6 C1 119.2(2) . . ? C5 C6 C7 120.0(2) . . ? C1 C6 C7 120.8(2) . . ? N1 C7 C6 109.4(2) . . ? N1 C7 H7C 109.8 . . ? C6 C7 H7C 109.8 . . ? N1 C7 H7D 109.8 . . ? C6 C7 H7D 109.8 . . ? H7C C7 H7D 108.2 . . ? C8 N1 C7 114.0(2) . . ? C8 N1 Cu1 108.94(16) . . ? C7 N1 Cu1 111.39(17) . . ? C8 N1 H1 108(2) . . ? C7 N1 H1 113(2) . . ? Cu1 N1 H1 101(2) . . ? N1 C8 C10 113.2(2) . . ? N1 C8 C9 108.0(2) . . ? C10 C8 C9 113.9(2) . . ? N1 C8 H8 107.1 . . ? C10 C8 H8 107.1 . . ? C9 C8 H8 107.1 . . ? O3 C9 O2 123.1(3) . . ? O3 C9 C8 119.7(2) . . ? O2 C9 C8 117.0(2) . . ? C8 C10 H10A 109.5 . . ? C8 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C8 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C9 O2 Cu1 115.61(19) . . ? C11 O4 Cu2 122.56(16) . . ? C11 O4 Cu1 133.72(17) . . ? Cu2 O4 Cu1 99.70(9) . . ? O4 C11 C12 120.4(2) . . ? O4 C11 C16 120.6(2) . . ? C12 C11 C16 118.9(2) . . ? C13 C12 C11 120.9(3) . . ? C13 C12 H12 119.6 . . ? C11 C12 H12 119.6 . . ? C14 C13 C12 119.7(3) . . ? C14 C13 H13 120.1 . . ? C12 C13 H13 120.1 . . ? C13 C14 C15 120.3(2) . . ? C13 C14 Br2 120.8(2) . . ? C15 C14 Br2 118.8(2) . . ? C14 C15 C16 120.5(2) . . ? C14 C15 H15 119.8 . . ? C16 C15 H15 119.8 . . ? C15 C16 C11 119.6(2) . . ? C15 C16 C17 118.1(2) . . ? C11 C16 C17 121.8(2) . . ? N2 C17 C16 117.2(3) . . ? N2 C17 H17A 108.0 . . ? C16 C17 H17A 108.0 . . ? N2 C17 H17B 108.0 . . ? C16 C17 H17B 108.0 . . ? H17A C17 H17B 107.3 . . ? C17 N2 C18 119.8(2) . . ? C17 N2 Cu2 116.48(18) . . ? C18 N2 Cu2 103.04(18) . . ? C17 N2 H2 109(2) . . ? C18 N2 H2 99(2) . . ? Cu2 N2 H2 108(2) . . ? N2 C18 C20 115.8(3) . . ? N2 C18 C19 103.6(2) . . ? C20 C18 C19 112.9(2) . . ? N2 C18 H18 108.0 . . ? C20 C18 H18 108.0 . . ? C19 C18 H18 108.0 . . ? O6 C19 O5 123.5(3) . . ? O6 C19 C18 120.7(3) . . ? O5 C19 C18 115.8(2) . . ? C18 C20 H20A 109.5 . . ? C18 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C18 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C19 O5 Cu2 112.13(18) . . ? Cu1 O7 H7A 109(3) . . ? Cu1 O7 H7B 120(3) . . ? H7A O7 H7B 100(3) . . ? H8A O8 H8B 97(3) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O7 H7A O6 0.77(2) 2.09(2) 2.807(3) 157(4) 2_756 O7 H7A O1 0.77(2) 2.98(4) 3.107(3) 92(3) . O8 H8A O6 0.79(2) 2.70(2) 3.488(4) 179(4) 2_746 O8 H8B O3 0.79(2) 2.03(2) 2.811(3) 169(4) 2_645 N1 H1 O7 0.83(4) 2.65(4) 3.098(3) 116(3) . N1 H1 Br1 0.83(4) 2.94(4) 3.744(2) 163(3) 2_656 N2 H2 O5 0.99(4) 2.05(4) 2.942(3) 149(3) 2_756 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 1.734 _refine_diff_density_min -0.816 _refine_diff_density_rms 0.094 _database_code_depnum_ccdc_archive 'CCDC 965512' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_Compound_6a # data_d033 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H28 Br2 Cu2 N2 O10' _chemical_formula_weight 743.34 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' O O 0.0106 0.0060 '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 13.093(3) _cell_length_b 6.9457(15) _cell_length_c 14.027(3) _cell_angle_alpha 90.00 _cell_angle_beta 99.983(4) _cell_angle_gamma 90.00 _cell_volume 1256.3(5) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 1890 _cell_measurement_theta_min 2.95 _cell_measurement_theta_max 27.47 _exptl_crystal_description Block _exptl_crystal_colour Green _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas 'Not Measured' _exptl_crystal_density_diffrn 1.965 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 740 _exptl_absorpt_coefficient_mu 4.931 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.2559 _exptl_absorpt_correction_T_max 0.7563 _exptl_absorpt_process_details 'Sadabs, (Sheldrick 2008)' _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 '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 8115 _diffrn_reflns_av_R_equivalents 0.0541 _diffrn_reflns_av_sigmaI/netI 0.0623 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.95 _diffrn_reflns_theta_max 27.50 _reflns_number_total 2872 _reflns_number_gt 2309 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0471P)^2^+9.2655P] 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 2872 _refine_ls_number_parameters 176 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0794 _refine_ls_R_factor_gt 0.0621 _refine_ls_wR_factor_ref 0.1477 _refine_ls_wR_factor_gt 0.1415 _refine_ls_goodness_of_fit_ref 1.131 _refine_ls_restrained_S_all 1.131 _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 0.53796(6) 0.54866(12) 0.40807(5) 0.0185(2) Uani 1 1 d . . . Br1 Br 1.04324(5) 0.41979(11) 0.70235(5) 0.0274(2) Uani 1 1 d . . . O1 O 0.5874(3) 0.4362(7) 0.5350(3) 0.0166(9) Uani 1 1 d . . . O2 O 0.4894(3) 0.6536(7) 0.2808(3) 0.0213(10) Uani 1 1 d . . . O3 O 0.5289(4) 0.6811(8) 0.1353(3) 0.0294(12) Uani 1 1 d . . . N1 N 0.6734(4) 0.5293(9) 0.3640(4) 0.0179(11) Uani 1 1 d . . . H1N H 0.717(8) 0.612(14) 0.391(7) 0.05(3) Uiso 1 1 d . . . C1 C 0.6894(5) 0.4285(9) 0.5725(4) 0.0151(12) Uani 1 1 d . . . C2 C 0.7241(5) 0.4625(9) 0.6713(4) 0.0145(12) Uani 1 1 d . . . H2 H 0.6750 0.4896 0.7121 0.017 Uiso 1 1 calc R . . C3 C 0.8285(5) 0.4572(9) 0.7103(4) 0.0170(12) Uani 1 1 d . . . H3 H 0.8512 0.4793 0.7774 0.020 Uiso 1 1 calc R . . C4 C 0.8989(4) 0.4196(9) 0.6509(4) 0.0164(12) Uani 1 1 d . . . C5 C 0.8671(5) 0.3856(9) 0.5523(4) 0.0173(13) Uani 1 1 d . . . H5 H 0.9171 0.3606 0.5122 0.021 Uiso 1 1 calc R . . C6 C 0.7629(4) 0.3881(8) 0.5130(4) 0.0134(12) Uani 1 1 d . . . C7 C 0.7296(5) 0.3526(9) 0.4066(4) 0.0161(12) Uani 1 1 d . . . H7A H 0.6833 0.2391 0.3960 0.019 Uiso 1 1 calc R . . H7B H 0.7909 0.3278 0.3758 0.019 Uiso 1 1 calc R . . C8 C 0.6534(5) 0.5347(9) 0.2582(4) 0.0165(13) Uani 1 1 d . . . H8A H 0.6522 0.4018 0.2324 0.020 Uiso 1 1 calc R . . H8B H 0.7098 0.6059 0.2349 0.020 Uiso 1 1 calc R . . C9 C 0.5511(5) 0.6313(9) 0.2216(4) 0.0163(12) Uani 1 1 d . . . C1S C 0.8715(9) 0.8774(14) 0.5192(8) 0.070(4) Uani 1 1 d . . . H1S1 H 0.8855 1.0085 0.5439 0.104 Uiso 1 1 calc R . . H1S2 H 0.9352 0.8215 0.5035 0.104 Uiso 1 1 calc R . . H1S3 H 0.8470 0.7986 0.5687 0.104 Uiso 1 1 calc R . . O1S O 0.7949(5) 0.8827(9) 0.4353(4) 0.0402(14) Uani 1 1 d . . . H1S H 0.7359 0.8849 0.4512 0.060 Uiso 1 1 calc R . . O1W O 0.6009(5) 0.8845(9) 0.4699(4) 0.0386(13) Uani 1 1 d D . . H1X H 0.593(7) 0.858(13) 0.527(3) 0.046 Uiso 1 1 d D . . H1Y H 0.591(7) 1.002(5) 0.451(7) 0.046 Uiso 1 1 d D . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.0113(4) 0.0400(5) 0.0046(3) 0.0036(3) 0.0028(3) 0.0072(3) Br1 0.0107(3) 0.0456(5) 0.0237(4) 0.0057(3) -0.0031(2) -0.0005(3) O1 0.011(2) 0.034(3) 0.0052(17) 0.0016(17) 0.0003(15) 0.0015(18) O2 0.013(2) 0.040(3) 0.0102(19) 0.0037(19) 0.0006(17) 0.005(2) O3 0.025(3) 0.058(3) 0.0060(19) 0.009(2) 0.0032(18) -0.003(2) N1 0.017(3) 0.027(3) 0.010(2) 0.000(2) 0.002(2) 0.004(2) C1 0.014(3) 0.021(3) 0.010(3) 0.005(2) 0.002(2) 0.002(2) C2 0.019(3) 0.017(3) 0.008(3) 0.000(2) 0.003(2) 0.001(2) C3 0.019(3) 0.018(3) 0.012(3) 0.003(2) -0.002(2) -0.002(2) C4 0.008(3) 0.021(3) 0.019(3) 0.005(2) -0.001(2) -0.001(2) C5 0.013(3) 0.020(3) 0.019(3) 0.002(2) 0.004(2) 0.000(2) C6 0.014(3) 0.013(3) 0.013(3) 0.003(2) 0.003(2) 0.003(2) C7 0.013(3) 0.022(3) 0.013(3) 0.000(2) 0.004(2) 0.001(2) C8 0.022(3) 0.017(3) 0.012(3) 0.002(2) 0.007(2) -0.001(2) C9 0.017(3) 0.025(3) 0.006(2) 0.000(2) -0.001(2) -0.005(2) C1S 0.081(8) 0.036(5) 0.072(7) -0.008(5) -0.039(6) 0.003(5) O1S 0.041(3) 0.049(4) 0.032(3) 0.003(3) 0.010(3) 0.003(3) O1W 0.048(4) 0.047(4) 0.022(3) 0.000(3) 0.011(3) -0.001(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 O2 1.931(4) . ? Cu1 O1 1.949(4) . ? Cu1 O1 1.949(4) 3_666 ? Cu1 N1 1.981(5) . ? Cu1 Cu1 2.9975(14) 3_666 ? Br1 C4 1.903(6) . ? O1 C1 1.349(7) . ? O1 Cu1 1.949(4) 3_666 ? O2 C9 1.266(7) . ? O3 C9 1.244(7) . ? N1 C8 1.462(7) . ? N1 C7 1.502(8) . ? C1 C2 1.401(8) . ? C1 C6 1.407(8) . ? C2 C3 1.383(9) . ? C3 C4 1.369(9) . ? C4 C5 1.394(9) . ? C5 C6 1.380(8) . ? C6 C7 1.500(8) . ? C8 C9 1.505(9) . ? C1S O1S 1.409(11) . ? 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 O2 Cu1 O1 178.5(2) . . ? O2 Cu1 O1 101.10(17) . 3_666 ? O1 Cu1 O1 79.47(19) . 3_666 ? O2 Cu1 N1 84.6(2) . . ? O1 Cu1 N1 94.83(19) . . ? O1 Cu1 N1 174.05(19) 3_666 . ? O2 Cu1 Cu1 140.82(13) . 3_666 ? O1 Cu1 Cu1 39.74(12) . 3_666 ? O1 Cu1 Cu1 39.74(12) 3_666 3_666 ? N1 Cu1 Cu1 134.55(15) . 3_666 ? C1 O1 Cu1 121.5(3) . . ? C1 O1 Cu1 133.6(3) . 3_666 ? Cu1 O1 Cu1 100.53(18) . 3_666 ? C9 O2 Cu1 114.5(4) . . ? C8 N1 C7 114.5(5) . . ? C8 N1 Cu1 107.6(4) . . ? C7 N1 Cu1 109.5(4) . . ? O1 C1 C2 120.5(5) . . ? O1 C1 C6 120.5(5) . . ? C2 C1 C6 118.9(5) . . ? C3 C2 C1 121.0(6) . . ? C4 C3 C2 119.2(6) . . ? C3 C4 C5 121.2(6) . . ? C3 C4 Br1 119.9(5) . . ? C5 C4 Br1 118.9(5) . . ? C6 C5 C4 120.0(6) . . ? C5 C6 C1 119.6(5) . . ? C5 C6 C7 119.5(5) . . ? C1 C6 C7 120.8(5) . . ? C6 C7 N1 107.4(5) . . ? N1 C8 C9 110.5(5) . . ? O3 C9 O2 122.4(6) . . ? O3 C9 C8 120.0(5) . . ? O2 C9 C8 117.5(5) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1N O1S 0.85(10) 2.18(10) 3.000(9) 163(9) . O1S H1S O1W 0.84 1.83 2.666(8) 172.9 . O1W H1X O3 0.85(2) 1.88(4) 2.691(7) 160(9) 4_576 O1W H1Y O3 0.86(2) 2.19(6) 2.905(8) 140(8) 2_655 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 1.378 _refine_diff_density_min -0.817 _refine_diff_density_rms 0.164 _database_code_depnum_ccdc_archive 'CCDC 965513' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_Compound_7a # data_d447jj _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C26 H36 Br2 Cu2 N2 O8.25 S' _chemical_formula_weight 827.53 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' O O 0.0106 0.0060 '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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 10.1311(4) _cell_length_b 12.0085(6) _cell_length_c 26.9697(13) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3281.1(3) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 9924 _cell_measurement_theta_min 2.27 _cell_measurement_theta_max 27.32 _exptl_crystal_description 'Thin Plate' _exptl_crystal_colour Green _exptl_crystal_size_max 0.29 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas 'Not measured' _exptl_crystal_density_diffrn 1.675 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1664 _exptl_absorpt_coefficient_mu 3.843 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.4020 _exptl_absorpt_correction_T_max 0.8022 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2008)' _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 D8 Advance' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 37560 _diffrn_reflns_av_R_equivalents 0.0416 _diffrn_reflns_av_sigmaI/netI 0.0452 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -35 _diffrn_reflns_limit_l_max 34 _diffrn_reflns_theta_min 2.15 _diffrn_reflns_theta_max 27.50 _reflns_number_total 7526 _reflns_number_gt 6633 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker AXS)' _computing_cell_refinement 'APEX2 v2013.6--2 (Bruker AXS)' _computing_data_reduction 'SAINT V8.32B (Bruker AXS Inc., 2013)' _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^)+(0.0306P)^2^+0.9622P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.000(7) _refine_ls_number_reflns 7526 _refine_ls_number_parameters 414 _refine_ls_number_restraints 71 _refine_ls_R_factor_all 0.0409 _refine_ls_R_factor_gt 0.0307 _refine_ls_wR_factor_ref 0.0677 _refine_ls_wR_factor_gt 0.0647 _refine_ls_goodness_of_fit_ref 1.044 _refine_ls_restrained_S_all 1.053 _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 0.58610(4) 0.69698(3) 0.524958(12) 0.01308(8) Uani 1 1 d . . . Cu2 Cu 0.64442(4) 0.51469(3) 0.450817(12) 0.01498(8) Uani 1 1 d . . . Br1 Br 0.78178(5) 0.25170(4) 0.694930(14) 0.04942(14) Uani 1 1 d U . . Br2 Br 0.66297(4) 0.98216(3) 0.279022(12) 0.03408(10) Uani 1 1 d U . . O1 O 0.6468(2) 0.54529(17) 0.52137(7) 0.0175(4) Uani 1 1 d . . . O2 O 0.4850(2) 0.83112(17) 0.52527(7) 0.0158(4) Uani 1 1 d . . . O3 O 0.3749(2) 0.94641(19) 0.57501(7) 0.0177(5) Uani 1 1 d . . . O4 O 0.5953(2) 0.67174(17) 0.45291(7) 0.0148(4) Uani 1 1 d . . . O5 O 0.6609(2) 0.35719(17) 0.45201(7) 0.0176(4) Uani 1 1 d . . . O6 O 0.6371(2) 0.2062(2) 0.40538(9) 0.0264(5) Uani 1 1 d . . . O7 O 0.7897(2) 0.7622(2) 0.54327(8) 0.0209(5) Uani 1 1 d D . . H7A H 0.815(3) 0.8291(13) 0.5400(13) 0.025 Uiso 1 1 d D . . H7B H 0.849(3) 0.724(3) 0.5293(11) 0.025 Uiso 1 1 d D . . O1W O 0.8080(7) 0.6679(8) 0.6426(3) 0.0164(19) Uani 0.25 1 d P . . N1 N 0.5446(2) 0.6854(2) 0.59718(9) 0.0145(5) Uani 1 1 d . . . H1 H 0.619(4) 0.690(3) 0.6129(12) 0.017 Uiso 1 1 d . . . N2 N 0.6384(3) 0.5016(2) 0.37781(8) 0.0124(5) Uani 1 1 d . . . H2 H 0.713(4) 0.520(3) 0.3712(11) 0.015 Uiso 1 1 d . . . C1 C 0.6817(3) 0.4838(3) 0.56129(10) 0.0163(6) Uani 1 1 d . . . C2 C 0.7934(3) 0.4178(3) 0.56041(11) 0.0200(7) Uani 1 1 d . . . H2A H 0.8485 0.4179 0.5319 0.024 Uiso 1 1 calc R . . C3 C 0.8262(4) 0.3510(3) 0.60094(12) 0.0260(8) Uani 1 1 d . . . H3 H 0.9027 0.3053 0.6001 0.031 Uiso 1 1 calc R . . C4 C 0.7459(4) 0.3525(3) 0.64204(12) 0.0277(8) Uani 1 1 d . . . C5 C 0.6371(4) 0.4213(3) 0.64504(12) 0.0259(8) Uani 1 1 d . . . H5 H 0.5846 0.4223 0.6742 0.031 Uiso 1 1 calc R . . C6 C 0.6049(3) 0.4893(3) 0.60483(11) 0.0176(7) Uani 1 1 d . . . C7 C 0.4937(3) 0.5716(3) 0.60834(12) 0.0191(7) Uani 1 1 d . . . H7C H 0.4235 0.5516 0.5844 0.023 Uiso 1 1 calc R . . H7D H 0.4555 0.5700 0.6421 0.023 Uiso 1 1 calc R . . C8 C 0.4557(3) 0.7783(3) 0.61154(10) 0.0173(7) Uani 1 1 d . . . H8 H 0.3675 0.7449 0.6191 0.021 Uiso 1 1 calc R . . C9 C 0.4361(3) 0.8596(3) 0.56769(11) 0.0150(6) Uani 1 1 d . . . C10 C 0.5018(4) 0.8409(3) 0.65880(11) 0.0269(8) Uani 1 1 d . . . H10 H 0.4346 0.8998 0.6658 0.032 Uiso 1 1 calc R . . C11 C 0.6328(4) 0.8995(3) 0.65122(14) 0.0383(10) Uani 1 1 d . . . H11A H 0.6538 0.9440 0.6806 0.057 Uiso 1 1 calc R . . H11B H 0.6270 0.9483 0.6222 0.057 Uiso 1 1 calc R . . H11C H 0.7023 0.8440 0.6459 0.057 Uiso 1 1 calc R . . C12 C 0.5041(4) 0.7630(4) 0.70355(12) 0.0390(10) Uani 1 1 d . . . H12A H 0.5651 0.7013 0.6971 0.058 Uiso 1 1 calc R . . H12B H 0.4153 0.7334 0.7093 0.058 Uiso 1 1 calc R . . H12C H 0.5335 0.8042 0.7329 0.058 Uiso 1 1 calc R . . C13 C 0.6013(3) 0.7416(3) 0.41382(10) 0.0146(6) Uani 1 1 d . . . C14 C 0.6259(3) 0.8550(3) 0.42096(11) 0.0144(6) Uani 1 1 d . . . H14 H 0.6333 0.8829 0.4538 0.017 Uiso 1 1 calc R . . C15 C 0.6398(3) 0.9273(3) 0.38167(11) 0.0186(7) Uani 1 1 d . . . H15 H 0.6550 1.0044 0.3871 0.022 Uiso 1 1 calc R . . C16 C 0.6310(4) 0.8847(3) 0.33408(11) 0.0213(7) Uani 1 1 d . . . C17 C 0.5998(3) 0.7734(3) 0.32593(11) 0.0220(7) Uani 1 1 d . . . H17 H 0.5896 0.7469 0.2930 0.026 Uiso 1 1 calc R . . C18 C 0.5835(3) 0.7007(3) 0.36525(10) 0.0152(6) Uani 1 1 d . . . C19 C 0.5424(3) 0.5817(3) 0.35632(11) 0.0157(7) Uani 1 1 d . . . H19A H 0.4545 0.5690 0.3713 0.019 Uiso 1 1 calc R . . H19B H 0.5350 0.5685 0.3202 0.019 Uiso 1 1 calc R . . C20 C 0.6210(3) 0.3824(3) 0.36419(11) 0.0175(7) Uani 1 1 d . . . H20 H 0.5276 0.3725 0.3529 0.021 Uiso 1 1 calc R . . C21 C 0.6412(3) 0.3078(3) 0.41013(11) 0.0177(6) Uani 1 1 d . . . C22 C 0.7120(4) 0.3428(3) 0.32156(12) 0.0263(8) Uani 1 1 d . . . H22 H 0.6837 0.2656 0.3126 0.032 Uiso 1 1 calc R . . C23 C 0.8564(4) 0.3359(3) 0.33797(12) 0.0298(8) Uani 1 1 d . . . H23A H 0.9117 0.3159 0.3095 0.045 Uiso 1 1 calc R . . H23B H 0.8654 0.2791 0.3638 0.045 Uiso 1 1 calc R . . H23C H 0.8844 0.4083 0.3511 0.045 Uiso 1 1 calc R . . C24 C 0.6975(5) 0.4140(4) 0.27485(13) 0.0426(11) Uani 1 1 d . . . H24A H 0.6051 0.4137 0.2641 0.064 Uiso 1 1 calc R . . H24B H 0.7531 0.3833 0.2485 0.064 Uiso 1 1 calc R . . H24C H 0.7250 0.4905 0.2821 0.064 Uiso 1 1 calc R . . S1 S 0.78860(13) 1.05306(10) 0.50234(6) 0.0250(4) Uani 0.719(4) 1 d PDU A 1 O1S O 0.8597(3) 0.9883(3) 0.54300(13) 0.0262(8) Uani 0.719(4) 1 d PDU A 1 S1A S 0.8200(3) 1.0837(3) 0.53196(14) 0.0295(12) Uani 0.281(4) 1 d PDU A 2 O1SA O 0.8384(10) 0.9642(5) 0.5143(4) 0.039(2) Uani 0.281(4) 1 d PDU A 2 C1S C 0.8870(3) 1.1687(3) 0.48673(12) 0.0272(8) Uani 1 1 d D . . H1SA H 0.9694 1.1430 0.4716 0.041 Uiso 0.719(4) 1 calc PR A 1 H1SB H 0.9070 1.2115 0.5167 0.041 Uiso 0.719(4) 1 calc PR A 1 H1SC H 0.8392 1.2161 0.4632 0.041 Uiso 0.719(4) 1 calc PR A 1 H1SD H 0.9829 1.1587 0.4859 0.041 Uiso 0.281(4) 1 calc PR A 2 H1SE H 0.8664 1.2467 0.4943 0.041 Uiso 0.281(4) 1 calc PR A 2 H1SF H 0.8495 1.1491 0.4544 0.041 Uiso 0.281(4) 1 calc PR A 2 C2S C 0.6528(3) 1.1196(3) 0.52872(15) 0.0386(9) Uani 1 1 d D . . H2SA H 0.5890 1.0638 0.5399 0.058 Uiso 0.719(4) 1 calc PR A 1 H2SB H 0.6113 1.1681 0.5040 0.058 Uiso 0.719(4) 1 calc PR A 1 H2SC H 0.6819 1.1645 0.5570 0.058 Uiso 0.719(4) 1 calc PR A 1 H2SD H 0.6037 1.0789 0.5542 0.058 Uiso 0.281(4) 1 calc PR A 2 H2SE H 0.6182 1.1002 0.4959 0.058 Uiso 0.281(4) 1 calc PR A 2 H2SF H 0.6430 1.1999 0.5342 0.058 Uiso 0.281(4) 1 calc PR A 2 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 0.01452(18) 0.01243(19) 0.01227(16) -0.00018(15) 0.00198(14) 0.00341(15) Cu2 0.02333(19) 0.00914(18) 0.01249(16) -0.00018(14) 0.00024(14) 0.00099(16) Br1 0.0680(3) 0.0553(3) 0.02501(19) 0.01827(19) 0.00724(18) 0.0406(2) Br2 0.0634(3) 0.01965(19) 0.01917(16) 0.00671(14) 0.00426(16) -0.00492(18) O1 0.0303(12) 0.0121(11) 0.0101(9) 0.0007(8) 0.0012(9) 0.0066(9) O2 0.0184(11) 0.0160(12) 0.0129(10) -0.0018(9) 0.0001(8) 0.0050(9) O3 0.0187(12) 0.0175(12) 0.0170(10) -0.0034(9) -0.0010(8) 0.0076(9) O4 0.0208(11) 0.0113(11) 0.0123(9) 0.0021(8) 0.0024(8) 0.0011(9) O5 0.0207(12) 0.0110(11) 0.0210(11) 0.0003(9) 0.0013(9) -0.0006(9) O6 0.0277(13) 0.0109(12) 0.0406(13) -0.0034(10) -0.0059(11) -0.0014(10) O7 0.0161(12) 0.0204(13) 0.0262(12) -0.0039(10) 0.0017(9) -0.0013(10) O1W 0.003(4) 0.027(5) 0.019(4) -0.008(4) -0.003(3) 0.000(3) N1 0.0095(13) 0.0171(15) 0.0168(13) 0.0002(11) -0.0010(10) 0.0054(11) N2 0.0113(12) 0.0091(14) 0.0168(12) -0.0030(10) 0.0007(9) -0.0016(11) C1 0.0195(16) 0.0133(16) 0.0159(14) -0.0016(12) 0.0000(11) 0.0014(13) C2 0.0248(18) 0.0184(18) 0.0170(15) -0.0011(13) 0.0030(13) 0.0040(14) C3 0.026(2) 0.029(2) 0.0235(17) 0.0012(15) -0.0022(14) 0.0138(15) C4 0.041(2) 0.025(2) 0.0173(16) 0.0067(15) -0.0040(14) 0.0133(16) C5 0.032(2) 0.028(2) 0.0171(15) 0.0073(14) 0.0054(14) 0.0104(16) C6 0.0216(17) 0.0144(17) 0.0170(14) 0.0012(13) -0.0001(12) 0.0028(13) C7 0.0174(18) 0.0214(19) 0.0185(16) 0.0053(13) 0.0044(12) 0.0044(14) C8 0.0195(17) 0.0199(19) 0.0125(14) -0.0015(12) 0.0015(11) 0.0076(13) C9 0.0125(16) 0.0159(17) 0.0167(15) -0.0039(12) -0.0014(11) 0.0005(12) C10 0.042(2) 0.026(2) 0.0134(15) -0.0054(14) -0.0029(14) 0.0151(16) C11 0.051(3) 0.033(2) 0.0310(19) -0.0086(17) -0.0178(18) -0.001(2) C12 0.052(3) 0.053(3) 0.0117(16) 0.0014(17) -0.0018(15) 0.020(2) C13 0.0139(15) 0.0164(16) 0.0135(13) 0.0009(12) 0.0015(11) 0.0005(12) C14 0.0160(17) 0.0126(16) 0.0147(14) -0.0033(12) 0.0018(11) -0.0006(12) C15 0.0225(17) 0.0109(16) 0.0224(16) 0.0011(12) 0.0028(13) -0.0009(14) C16 0.031(2) 0.0172(18) 0.0158(15) 0.0077(13) 0.0026(13) -0.0028(14) C17 0.0288(19) 0.023(2) 0.0146(14) 0.0005(13) -0.0003(13) -0.0001(14) C18 0.0173(15) 0.0134(16) 0.0150(14) -0.0010(12) -0.0016(12) 0.0015(14) C19 0.0186(17) 0.0137(17) 0.0147(14) -0.0008(12) -0.0059(12) 0.0005(12) C20 0.0181(18) 0.0109(16) 0.0235(16) -0.0072(12) -0.0031(12) 0.0001(12) C21 0.0074(14) 0.0156(17) 0.0300(16) -0.0021(13) 0.0002(12) 0.0014(13) C22 0.032(2) 0.024(2) 0.0229(16) -0.0106(14) -0.0035(15) 0.0047(16) C23 0.030(2) 0.031(2) 0.0286(18) -0.0108(15) 0.0078(15) 0.0057(17) C24 0.052(3) 0.053(3) 0.0225(19) -0.0092(19) 0.0049(17) 0.015(2) S1 0.0261(7) 0.0171(7) 0.0317(9) 0.0009(5) -0.0052(6) 0.0012(5) O1S 0.0275(17) 0.0187(18) 0.0323(18) 0.0034(15) -0.0118(15) 0.0048(15) S1A 0.0228(18) 0.041(2) 0.025(2) 0.0093(16) -0.0035(14) 0.0106(14) O1SA 0.037(4) 0.028(4) 0.050(4) 0.017(3) 0.007(4) 0.005(3) C1S 0.0196(19) 0.020(2) 0.042(2) 0.0042(16) 0.0009(14) 0.0033(13) C2S 0.026(2) 0.030(2) 0.060(3) 0.017(2) 0.0056(19) 0.0040(17) _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 O2 1.909(2) . ? Cu1 O1 1.925(2) . ? Cu1 O4 1.9688(19) . ? Cu1 N1 1.997(2) . ? Cu1 O7 2.261(2) . ? Cu1 Cu2 3.0231(5) . ? Cu2 O5 1.899(2) . ? Cu2 O1 1.9382(19) . ? Cu2 O4 1.951(2) . ? Cu2 N2 1.976(2) . ? Cu2 O3 2.481(2) 4_566 ? Br1 C4 1.905(3) . ? Br2 C16 1.918(3) . ? O1 C1 1.353(4) . ? O2 C9 1.293(3) . ? O3 C9 1.228(4) . ? O4 C13 1.349(4) . ? O5 C21 1.291(4) . ? O6 C21 1.226(4) . ? N1 C8 1.485(4) . ? N1 C7 1.492(4) . ? N2 C19 1.486(4) . ? N2 C20 1.488(4) . ? C1 C2 1.381(4) . ? C1 C6 1.410(4) . ? C2 C3 1.396(4) . ? C3 C4 1.375(5) . ? C4 C5 1.380(5) . ? C5 C6 1.397(4) . ? C6 C7 1.501(4) . ? C8 C9 1.547(4) . ? C8 C10 1.552(4) . ? C10 C11 1.515(6) . ? C10 C12 1.528(5) . ? C13 C14 1.397(4) . ? C13 C18 1.411(4) . ? C14 C15 1.377(4) . ? C15 C16 1.385(4) . ? C16 C17 1.391(5) . ? C17 C18 1.383(4) . ? C18 C19 1.507(4) . ? C20 C21 1.543(4) . ? C20 C22 1.549(4) . ? C22 C24 1.529(5) . ? C22 C23 1.530(5) . ? S1 O1S 1.525(3) . ? S1 C2S 1.743(3) . ? S1 C1S 1.761(3) . ? S1A O1SA 1.524(5) . ? S1A C1S 1.729(4) . ? S1A C2S 1.750(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 O2 Cu1 O1 165.97(10) . . ? O2 Cu1 O4 99.19(8) . . ? O1 Cu1 O4 77.85(8) . . ? O2 Cu1 N1 86.64(10) . . ? O1 Cu1 N1 92.89(10) . . ? O4 Cu1 N1 164.09(10) . . ? O2 Cu1 O7 101.30(9) . . ? O1 Cu1 O7 92.72(9) . . ? O4 Cu1 O7 103.03(8) . . ? N1 Cu1 O7 90.17(10) . . ? O2 Cu1 Cu2 135.96(6) . . ? O1 Cu1 Cu2 38.66(6) . . ? O4 Cu1 Cu2 39.33(6) . . ? N1 Cu1 Cu2 129.48(8) . . ? O7 Cu1 Cu2 102.54(6) . . ? O5 Cu2 O1 99.85(9) . . ? O5 Cu2 O4 169.92(9) . . ? O1 Cu2 O4 77.96(8) . . ? O5 Cu2 N2 86.58(10) . . ? O1 Cu2 N2 173.55(10) . . ? O4 Cu2 N2 95.61(9) . . ? O5 Cu2 O3 96.29(8) . 4_566 ? O1 Cu2 O3 103.19(8) . 4_566 ? O4 Cu2 O3 93.78(8) . 4_566 ? N2 Cu2 O3 76.37(9) . 4_566 ? O5 Cu2 Cu1 136.65(6) . . ? O1 Cu2 Cu1 38.35(6) . . ? O4 Cu2 Cu1 39.75(6) . . ? N2 Cu2 Cu1 135.28(7) . . ? O3 Cu2 Cu1 103.49(5) 4_566 . ? C1 O1 Cu1 124.09(18) . . ? C1 O1 Cu2 132.92(19) . . ? Cu1 O1 Cu2 102.99(9) . . ? C9 O2 Cu1 115.67(19) . . ? C13 O4 Cu2 124.57(18) . . ? C13 O4 Cu1 132.66(19) . . ? Cu2 O4 Cu1 100.92(9) . . ? C21 O5 Cu2 115.4(2) . . ? C8 N1 C7 115.2(2) . . ? C8 N1 Cu1 109.27(18) . . ? C7 N1 Cu1 109.46(19) . . ? C19 N2 C20 116.7(2) . . ? C19 N2 Cu2 110.94(18) . . ? C20 N2 Cu2 109.03(18) . . ? O1 C1 C2 120.9(3) . . ? O1 C1 C6 119.5(3) . . ? C2 C1 C6 119.6(3) . . ? C1 C2 C3 120.7(3) . . ? C4 C3 C2 118.9(3) . . ? C3 C4 C5 121.8(3) . . ? C3 C4 Br1 118.9(3) . . ? C5 C4 Br1 119.2(3) . . ? C4 C5 C6 119.5(3) . . ? C5 C6 C1 119.3(3) . . ? C5 C6 C7 120.8(3) . . ? C1 C6 C7 119.8(3) . . ? N1 C7 C6 109.4(3) . . ? N1 C8 C9 110.6(2) . . ? N1 C8 C10 113.3(3) . . ? C9 C8 C10 111.1(3) . . ? O3 C9 O2 124.1(3) . . ? O3 C9 C8 118.5(3) . . ? O2 C9 C8 117.4(3) . . ? C11 C10 C12 112.2(3) . . ? C11 C10 C8 112.2(3) . . ? C12 C10 C8 110.9(3) . . ? O4 C13 C14 120.4(3) . . ? O4 C13 C18 120.2(3) . . ? C14 C13 C18 119.4(3) . . ? C15 C14 C13 121.8(3) . . ? C14 C15 C16 118.3(3) . . ? C15 C16 C17 121.1(3) . . ? C15 C16 Br2 118.8(2) . . ? C17 C16 Br2 120.2(2) . . ? C18 C17 C16 120.8(3) . . ? C17 C18 C13 118.5(3) . . ? C17 C18 C19 120.6(3) . . ? C13 C18 C19 120.9(3) . . ? N2 C19 C18 111.8(2) . . ? N2 C20 C21 110.2(2) . . ? N2 C20 C22 114.1(3) . . ? C21 C20 C22 109.8(3) . . ? O6 C21 O5 123.6(3) . . ? O6 C21 C20 119.3(3) . . ? O5 C21 C20 117.1(3) . . ? C24 C22 C23 111.1(3) . . ? C24 C22 C20 112.5(3) . . ? C23 C22 C20 111.8(3) . . ? O1S S1 C2S 108.3(2) . . ? O1S S1 C1S 107.86(19) . . ? C2S S1 C1S 100.51(18) . . ? O1SA S1A C1S 106.7(4) . . ? O1SA S1A C2S 109.6(5) . . ? C1S S1A C2S 101.5(2) . . ? S1A C1S S1 31.08(14) . . ? S1 C2S S1A 31.07(14) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N2 H2 O3 0.80(4) 2.23(3) 2.784(3) 127(3) 4_566 N1 H1 O1W 0.87(4) 2.09(4) 2.943(8) 167(3) . O7 H7B O2 0.846(10) 2.121(15) 2.931(3) 160(3) 4_566 O7 H7A S1 0.849(10) 2.887(19) 3.663(3) 153(3) . O7 H7A O1S 0.849(10) 1.965(12) 2.806(4) 170(3) . O7 H7A O1SA 0.849(10) 1.779(17) 2.595(8) 161(4) . _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 1.676 _refine_diff_density_min -1.093 _refine_diff_density_rms 0.092 _database_code_depnum_ccdc_archive 'CCDC 965514' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_Compound_8a # data_d448jj _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C28 H40 Br2 Cu2 N2 O8 S' _chemical_formula_weight 851.58 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' O O 0.0106 0.0060 '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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x+1/2, -y, z+1/2' _cell_length_a 10.3703(10) _cell_length_b 11.8761(11) _cell_length_c 26.984(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3323.3(5) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 9390 _cell_measurement_theta_min 2.48 _cell_measurement_theta_max 26.86 _exptl_crystal_description Block _exptl_crystal_colour green _exptl_crystal_size_max 0.11 _exptl_crystal_size_mid 0.07 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas 'Not measured' _exptl_crystal_density_diffrn 1.702 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1720 _exptl_absorpt_coefficient_mu 3.796 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.6715 _exptl_absorpt_correction_T_max 0.8661 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2008)' _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 'D8 VENTURE' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 156446 _diffrn_reflns_av_R_equivalents 0.0626 _diffrn_reflns_av_sigmaI/netI 0.0255 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -35 _diffrn_reflns_limit_l_max 35 _diffrn_reflns_theta_min 2.10 _diffrn_reflns_theta_max 27.50 _reflns_number_total 7644 _reflns_number_gt 7106 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker AXS)' _computing_cell_refinement 'APEX2 v2013.6--2 (Bruker AXS)' _computing_data_reduction 'SAINT V8.32B (Bruker AXS Inc., 2013)' _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^)+(0.0285P)^2^+4.7862P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.001(7) _refine_ls_number_reflns 7644 _refine_ls_number_parameters 414 _refine_ls_number_restraints 15 _refine_ls_R_factor_all 0.0339 _refine_ls_R_factor_gt 0.0290 _refine_ls_wR_factor_ref 0.0653 _refine_ls_wR_factor_gt 0.0636 _refine_ls_goodness_of_fit_ref 1.048 _refine_ls_restrained_S_all 1.082 _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 0.55342(3) 0.29225(3) 0.473245(13) 0.00956(8) Uani 1 1 d . . . Cu2 Cu 0.60372(4) 0.48033(3) 0.545304(13) 0.00998(8) Uani 1 1 d . . . Br1 Br 0.76196(4) 0.72944(4) 0.299614(14) 0.03699(11) Uani 1 1 d . . . Br2 Br 0.62831(4) 0.01272(3) 0.720160(12) 0.02817(9) Uani 1 1 d . . . O1 O 0.6173(2) 0.44515(17) 0.47544(8) 0.0138(4) Uani 1 1 d . . . O2 O 0.4554(2) 0.15537(18) 0.47284(8) 0.0138(4) Uani 1 1 d . . . O3 O 0.3348(2) 0.04595(19) 0.42459(8) 0.0143(5) Uani 1 1 d . . . O4 O 0.5582(2) 0.32090(16) 0.54488(8) 0.0104(4) Uani 1 1 d . . . O5 O 0.6307(2) 0.63926(17) 0.54327(8) 0.0123(4) Uani 1 1 d . . . O6 O 0.6023(2) 0.79384(18) 0.58807(8) 0.0172(5) Uani 1 1 d . . . O7 O 0.7568(2) 0.22873(19) 0.46119(9) 0.0184(5) Uani 1 1 d D . . H7A H 0.785(4) 0.1633(15) 0.4667(15) 0.022 Uiso 1 1 d D . . H7B H 0.810(3) 0.270(3) 0.4765(13) 0.022 Uiso 1 1 d D . . N1 N 0.5076(2) 0.3043(2) 0.40165(10) 0.0104(5) Uani 1 1 d . . . H1 H 0.576(4) 0.286(3) 0.3859(13) 0.013 Uiso 1 1 d . . . N2 N 0.5923(2) 0.4983(2) 0.61751(9) 0.0093(5) Uani 1 1 d . . . H2 H 0.673(4) 0.490(3) 0.6247(13) 0.011 Uiso 1 1 d . . . C1 C 0.6543(3) 0.5047(3) 0.43556(11) 0.0116(6) Uani 1 1 d . . . C2 C 0.7654(3) 0.5697(3) 0.43643(12) 0.0148(6) Uani 1 1 d . . . H2A H 0.8177 0.5705 0.4653 0.018 Uiso 1 1 calc R . . C3 C 0.8013(3) 0.6339(3) 0.39543(13) 0.0193(7) Uani 1 1 d . . . H3 H 0.8783 0.6772 0.3959 0.023 Uiso 1 1 calc R . . C4 C 0.7227(4) 0.6334(3) 0.35426(12) 0.0211(7) Uani 1 1 d . . . C5 C 0.6139(3) 0.5657(3) 0.35171(12) 0.0183(7) Uani 1 1 d . . . H5 H 0.5630 0.5645 0.3224 0.022 Uiso 1 1 calc R . . C6 C 0.5798(3) 0.4999(3) 0.39204(11) 0.0126(6) Uani 1 1 d . . . C7 C 0.4662(3) 0.4212(3) 0.38900(12) 0.0143(6) Uani 1 1 d . . . H7C H 0.3983 0.4460 0.4123 0.017 Uiso 1 1 calc R . . H7D H 0.4300 0.4226 0.3551 0.017 Uiso 1 1 calc R . . C8 C 0.4077(3) 0.2188(3) 0.38979(11) 0.0123(6) Uani 1 1 d . . . H8 H 0.3235 0.2598 0.3899 0.015 Uiso 1 1 calc R . . C9 C 0.3989(3) 0.1314(3) 0.43176(11) 0.0109(6) Uani 1 1 d . . . C10 C 0.4221(3) 0.1685(3) 0.33764(11) 0.0144(6) Uani 1 1 d . . . H10A H 0.4500 0.2294 0.3150 0.017 Uiso 1 1 calc R . . H10B H 0.3358 0.1434 0.3265 0.017 Uiso 1 1 calc R . . C11 C 0.5164(4) 0.0687(4) 0.33144(13) 0.0271(8) Uani 1 1 d . . . H11 H 0.4785 0.0029 0.3494 0.032 Uiso 1 1 calc R . . C12 C 0.6482(4) 0.0868(4) 0.35161(14) 0.0322(9) Uani 1 1 d . . . H12A H 0.6898 0.1487 0.3337 0.048 Uiso 1 1 calc R . . H12B H 0.6991 0.0179 0.3475 0.048 Uiso 1 1 calc R . . H12C H 0.6425 0.1056 0.3869 0.048 Uiso 1 1 calc R . . C13 C 0.5228(4) 0.0371(4) 0.27624(14) 0.0317(9) Uani 1 1 d . . . H13A H 0.5607 0.0995 0.2575 0.048 Uiso 1 1 calc R . . H13B H 0.4356 0.0220 0.2639 0.048 Uiso 1 1 calc R . . H13C H 0.5762 -0.0304 0.2721 0.048 Uiso 1 1 calc R . . C14 C 0.5674(3) 0.2524(2) 0.58457(11) 0.0092(6) Uani 1 1 d . . . C15 C 0.5920(3) 0.1377(3) 0.57777(11) 0.0114(6) Uani 1 1 d . . . H15 H 0.5985 0.1086 0.5451 0.014 Uiso 1 1 calc R . . C16 C 0.6069(3) 0.0657(3) 0.61760(11) 0.0129(6) Uani 1 1 d . . . H16 H 0.6226 -0.0123 0.6126 0.015 Uiso 1 1 calc R . . C17 C 0.5985(3) 0.1097(2) 0.66500(11) 0.0140(6) Uani 1 1 d . . . C18 C 0.5707(3) 0.2224(3) 0.67305(11) 0.0128(6) Uani 1 1 d . . . H18 H 0.5641 0.2503 0.7059 0.015 Uiso 1 1 calc R . . C19 C 0.5523(3) 0.2949(2) 0.63284(11) 0.0098(5) Uani 1 1 d . . . C20 C 0.5086(3) 0.4141(2) 0.64214(12) 0.0120(6) Uani 1 1 d . . . H20A H 0.4191 0.4231 0.6299 0.014 Uiso 1 1 calc R . . H20B H 0.5083 0.4285 0.6783 0.014 Uiso 1 1 calc R . . C21 C 0.5566(3) 0.6175(2) 0.62747(11) 0.0101(6) Uani 1 1 d . . . H21 H 0.4602 0.6200 0.6269 0.012 Uiso 1 1 calc R . . C22 C 0.6017(3) 0.6909(2) 0.58358(11) 0.0107(6) Uani 1 1 d . . . C23 C 0.5968(3) 0.6618(3) 0.67851(11) 0.0149(6) Uani 1 1 d . . . H23A H 0.5413 0.6254 0.7037 0.018 Uiso 1 1 calc R . . H23B H 0.5784 0.7436 0.6795 0.018 Uiso 1 1 calc R . . C24 C 0.7381(3) 0.6441(3) 0.69380(12) 0.0185(7) Uani 1 1 d . . . H24 H 0.7576 0.5618 0.6916 0.022 Uiso 1 1 calc R . . C25 C 0.8324(3) 0.7064(3) 0.66053(14) 0.0257(8) Uani 1 1 d . . . H25A H 0.8119 0.7869 0.6606 0.039 Uiso 1 1 calc R . . H25B H 0.8258 0.6771 0.6267 0.039 Uiso 1 1 calc R . . H25C H 0.9204 0.6952 0.6729 0.039 Uiso 1 1 calc R . . C26 C 0.7533(4) 0.6803(3) 0.74784(14) 0.0303(9) Uani 1 1 d . . . H26A H 0.8418 0.6654 0.7588 0.045 Uiso 1 1 calc R . . H26B H 0.6930 0.6377 0.7686 0.045 Uiso 1 1 calc R . . H26C H 0.7349 0.7609 0.7508 0.045 Uiso 1 1 calc R . . S1 S 0.27110(10) 0.55943(8) 0.50025(4) 0.0173(3) Uani 0.800(3) 1 d PDU A 1 S1A S 0.3077(3) 0.6109(3) 0.53506(14) 0.0242(14) Uani 0.200(3) 1 d PDU A 2 O1S O 0.3470(2) 0.4915(2) 0.53782(10) 0.0267(6) Uani 1 1 d D . . C1S C 0.1417(3) 0.6215(3) 0.53123(14) 0.0271(8) Uani 1 1 d D . . H1SA H 0.0820 0.5628 0.5424 0.041 Uiso 0.800(3) 1 calc PR A 1 H1SB H 0.0966 0.6729 0.5087 0.041 Uiso 0.800(3) 1 calc PR A 1 H1SC H 0.1737 0.6636 0.5599 0.041 Uiso 0.800(3) 1 calc PR A 1 H1SD H 0.1024 0.5840 0.5599 0.041 Uiso 0.200(3) 1 calc PR A 2 H1SE H 0.1118 0.5854 0.5007 0.041 Uiso 0.200(3) 1 calc PR A 2 H1SF H 0.1167 0.7011 0.5310 0.041 Uiso 0.200(3) 1 calc PR A 2 C2S C 0.3629(3) 0.6785(3) 0.48432(14) 0.0285(9) Uani 1 1 d D . . H2SA H 0.4403 0.6547 0.4663 0.043 Uiso 0.800(3) 1 calc PR A 1 H2SB H 0.3883 0.7186 0.5145 0.043 Uiso 0.800(3) 1 calc PR A 1 H2SC H 0.3114 0.7285 0.4633 0.043 Uiso 0.800(3) 1 calc PR A 1 H2SD H 0.4574 0.6760 0.4840 0.043 Uiso 0.200(3) 1 calc PR A 2 H2SE H 0.3341 0.7571 0.4850 0.043 Uiso 0.200(3) 1 calc PR A 2 H2SF H 0.3294 0.6416 0.4545 0.043 Uiso 0.200(3) 1 calc PR A 2 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 0.01142(17) 0.00939(17) 0.00786(16) -0.00037(14) -0.00176(14) -0.00295(14) Cu2 0.01506(17) 0.00642(15) 0.00846(16) -0.00034(13) 0.00033(14) -0.00069(14) Br1 0.0429(2) 0.0467(3) 0.02140(18) 0.01694(17) -0.00351(17) -0.0261(2) Br2 0.0568(3) 0.01487(16) 0.01280(15) 0.00461(13) 0.00041(16) 0.01172(16) O1 0.0211(11) 0.0110(10) 0.0094(10) 0.0006(8) -0.0008(9) -0.0055(9) O2 0.0151(11) 0.0154(11) 0.0108(10) 0.0001(9) -0.0018(9) -0.0052(9) O3 0.0129(11) 0.0165(12) 0.0134(11) -0.0007(9) -0.0003(8) -0.0057(9) O4 0.0158(10) 0.0067(9) 0.0086(10) -0.0005(8) -0.0016(9) -0.0012(8) O5 0.0155(11) 0.0081(9) 0.0135(10) 0.0011(8) 0.0001(9) -0.0005(8) O6 0.0225(11) 0.0073(10) 0.0219(12) -0.0006(9) 0.0025(10) -0.0007(10) O7 0.0132(11) 0.0158(12) 0.0261(13) -0.0029(10) -0.0020(9) 0.0006(9) N1 0.0083(12) 0.0125(13) 0.0105(12) -0.0020(10) -0.0004(10) -0.0045(10) N2 0.0072(12) 0.0074(12) 0.0133(12) -0.0007(9) 0.0001(9) 0.0019(10) C1 0.0140(14) 0.0097(14) 0.0110(13) -0.0017(11) 0.0028(11) -0.0002(12) C2 0.0164(16) 0.0139(15) 0.0140(15) -0.0009(12) -0.0028(12) -0.0031(13) C3 0.0191(17) 0.0187(17) 0.0200(17) -0.0006(14) 0.0023(14) -0.0112(13) C4 0.0304(19) 0.0194(17) 0.0134(16) 0.0057(13) 0.0046(14) -0.0075(15) C5 0.0196(17) 0.0222(16) 0.0129(15) 0.0033(13) -0.0059(13) -0.0069(14) C6 0.0124(14) 0.0124(15) 0.0130(14) 0.0010(12) -0.0017(11) -0.0019(12) C7 0.0127(16) 0.0143(15) 0.0158(15) 0.0048(12) -0.0035(12) -0.0010(12) C8 0.0099(13) 0.0140(14) 0.0129(14) 0.0000(12) -0.0020(11) -0.0013(12) C9 0.0062(13) 0.0140(14) 0.0124(14) -0.0021(11) 0.0024(12) 0.0020(12) C10 0.0122(16) 0.0192(15) 0.0118(15) 0.0000(12) -0.0029(12) -0.0043(12) C11 0.0255(19) 0.039(2) 0.0166(18) -0.0039(16) 0.0007(15) 0.0056(17) C12 0.033(2) 0.042(2) 0.0224(19) -0.0105(17) -0.0046(16) 0.0119(18) C13 0.028(2) 0.051(3) 0.0160(17) -0.0133(18) -0.0006(15) 0.0027(18) C14 0.0051(12) 0.0110(14) 0.0114(14) 0.0023(11) -0.0011(10) -0.0025(11) C15 0.0115(14) 0.0103(14) 0.0124(14) -0.0028(11) -0.0008(12) 0.0000(12) C16 0.0172(15) 0.0080(13) 0.0134(15) 0.0000(11) 0.0007(13) -0.0004(13) C17 0.0204(16) 0.0094(14) 0.0122(15) 0.0054(11) -0.0003(13) 0.0027(13) C18 0.0168(15) 0.0113(14) 0.0104(14) 0.0000(12) -0.0002(11) -0.0004(12) C19 0.0091(12) 0.0067(13) 0.0135(14) 0.0001(11) 0.0006(12) -0.0005(12) C20 0.0163(15) 0.0087(15) 0.0110(15) -0.0001(11) 0.0055(12) 0.0002(12) C21 0.0124(14) 0.0045(13) 0.0135(14) -0.0028(11) 0.0012(12) 0.0022(11) C22 0.0075(13) 0.0091(14) 0.0155(15) -0.0003(11) 0.0019(12) -0.0014(11) C23 0.0209(16) 0.0111(14) 0.0127(15) -0.0030(12) 0.0005(13) 0.0016(13) C24 0.0222(17) 0.0134(15) 0.0200(17) -0.0048(13) -0.0054(14) 0.0015(13) C25 0.0168(17) 0.0282(19) 0.032(2) -0.0037(17) -0.0047(15) -0.0006(15) C26 0.038(2) 0.029(2) 0.0239(19) -0.0091(16) -0.0139(17) 0.0053(18) S1 0.0162(5) 0.0126(5) 0.0231(6) -0.0011(4) -0.0033(4) -0.0002(4) S1A 0.018(2) 0.029(3) 0.026(3) 0.0034(19) -0.0092(18) 0.0095(18) O1S 0.0200(11) 0.0165(12) 0.0435(16) 0.0086(11) -0.0041(11) 0.0043(10) C1S 0.0185(17) 0.0254(18) 0.037(2) 0.0099(16) 0.0043(16) 0.0054(14) C2S 0.0169(17) 0.0238(18) 0.045(2) 0.0109(16) 0.0033(16) 0.0036(14) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 O2 1.917(2) . ? Cu1 O1 1.934(2) . ? Cu1 O4 1.963(2) . ? Cu1 N1 1.995(3) . ? Cu1 O7 2.264(2) . ? Cu1 Cu2 3.0070(5) . ? Cu2 O5 1.909(2) . ? Cu2 O1 1.936(2) . ? Cu2 O4 1.951(2) . ? Cu2 N2 1.964(2) . ? Cu2 O3 2.549(2) 2_556 ? Br1 C4 1.908(3) . ? Br2 C17 1.907(3) . ? O1 C1 1.344(4) . ? O2 C9 1.286(4) . ? O3 C9 1.229(4) . ? O4 C14 1.348(4) . ? O5 C22 1.284(4) . ? O6 C22 1.229(4) . ? O7 H7A 0.842(10) . ? O7 H7B 0.842(10) . ? N1 C8 1.485(4) . ? N1 C7 1.492(4) . ? N1 H1 0.85(4) . ? N2 C20 1.482(4) . ? N2 C21 1.488(3) . ? N2 H2 0.87(4) . ? C1 C2 1.387(4) . ? C1 C6 1.407(4) . ? C2 C3 1.394(5) . ? C2 H2A 0.9500 . ? C3 C4 1.378(5) . ? C3 H3 0.9500 . ? C4 C5 1.387(5) . ? C5 C6 1.386(4) . ? C5 H5 0.9500 . ? C6 C7 1.507(4) . ? C7 H7C 0.9900 . ? C7 H7D 0.9900 . ? C8 C10 1.536(4) . ? C8 C9 1.539(4) . ? C8 H8 1.0000 . ? C10 C11 1.546(5) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 C12 1.486(6) . ? C11 C13 1.538(5) . ? C11 H11 1.0000 . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C14 C15 1.398(4) . ? C14 C19 1.406(4) . ? C15 C16 1.382(4) . ? C15 H15 0.9500 . ? C16 C17 1.385(4) . ? C16 H16 0.9500 . ? C17 C18 1.385(4) . ? C18 C19 1.399(4) . ? C18 H18 0.9500 . ? C19 C20 1.507(4) . ? C20 H20A 0.9900 . ? C20 H20B 0.9900 . ? C21 C23 1.532(4) . ? C21 C22 1.543(4) . ? C21 H21 1.0000 . ? C23 C24 1.537(5) . ? C23 H23A 0.9900 . ? C23 H23B 0.9900 . ? C24 C25 1.520(5) . ? C24 C26 1.528(5) . ? C24 H24 1.0000 . ? C25 H25A 0.9800 . ? C25 H25B 0.9800 . ? C25 H25C 0.9800 . ? C26 H26A 0.9800 . ? C26 H26B 0.9800 . ? C26 H26C 0.9800 . ? S1 O1S 1.516(3) . ? S1 C1S 1.745(3) . ? S1 C2S 1.758(3) . ? S1A O1S 1.477(4) . ? S1A C2S 1.687(4) . ? S1A C1S 1.729(4) . ? C1S H1SA 0.9800 . ? C1S H1SB 0.9800 . ? C1S H1SC 0.9800 . ? C1S H1SD 0.9800 . ? C1S H1SE 0.9800 . ? C1S H1SF 0.9800 . ? C2S H2SA 0.9800 . ? C2S H2SB 0.9800 . ? C2S H2SC 0.9800 . ? C2S H2SD 0.9800 . ? C2S H2SE 0.9800 . ? C2S H2SF 0.9800 . ? 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 O2 Cu1 O1 167.94(10) . . ? O2 Cu1 O4 99.55(9) . . ? O1 Cu1 O4 78.37(8) . . ? O2 Cu1 N1 85.94(10) . . ? O1 Cu1 N1 92.51(10) . . ? O4 Cu1 N1 161.29(10) . . ? O2 Cu1 O7 102.17(9) . . ? O1 Cu1 O7 89.89(9) . . ? O4 Cu1 O7 100.12(9) . . ? N1 Cu1 O7 96.12(10) . . ? O2 Cu1 Cu2 136.51(7) . . ? O1 Cu1 Cu2 39.04(6) . . ? O4 Cu1 Cu2 39.67(6) . . ? N1 Cu1 Cu2 127.90(8) . . ? O7 Cu1 Cu2 100.30(6) . . ? O5 Cu2 O1 100.06(9) . . ? O5 Cu2 O4 174.09(10) . . ? O1 Cu2 O4 78.61(8) . . ? O5 Cu2 N2 85.98(10) . . ? O1 Cu2 N2 173.72(10) . . ? O4 Cu2 N2 95.55(9) . . ? O5 Cu2 O3 89.57(8) . 2_556 ? O1 Cu2 O3 102.45(8) . 2_556 ? O4 Cu2 O3 96.34(8) . 2_556 ? N2 Cu2 O3 75.74(9) . 2_556 ? O5 Cu2 Cu1 137.84(7) . . ? O1 Cu2 Cu1 38.98(6) . . ? O4 Cu2 Cu1 39.96(6) . . ? N2 Cu2 Cu1 135.39(7) . . ? O3 Cu2 Cu1 106.15(5) 2_556 . ? C1 O1 Cu1 124.57(19) . . ? C1 O1 Cu2 133.40(19) . . ? Cu1 O1 Cu2 101.98(10) . . ? C9 O2 Cu1 115.7(2) . . ? C14 O4 Cu2 124.29(18) . . ? C14 O4 Cu1 132.80(18) . . ? Cu2 O4 Cu1 100.37(9) . . ? C22 O5 Cu2 114.41(19) . . ? Cu1 O7 H7A 127(3) . . ? Cu1 O7 H7B 110(3) . . ? H7A O7 H7B 103(4) . . ? C8 N1 C7 112.7(2) . . ? C8 N1 Cu1 109.00(18) . . ? C7 N1 Cu1 110.92(19) . . ? C8 N1 H1 107(2) . . ? C7 N1 H1 111(2) . . ? Cu1 N1 H1 105(2) . . ? C20 N2 C21 114.5(2) . . ? C20 N2 Cu2 114.03(19) . . ? C21 N2 Cu2 107.31(18) . . ? C20 N2 H2 113(2) . . ? C21 N2 H2 108(2) . . ? Cu2 N2 H2 99(2) . . ? O1 C1 C2 121.1(3) . . ? O1 C1 C6 119.4(3) . . ? C2 C1 C6 119.5(3) . . ? C1 C2 C3 120.8(3) . . ? C1 C2 H2A 119.6 . . ? C3 C2 H2A 119.6 . . ? C4 C3 C2 118.7(3) . . ? C4 C3 H3 120.7 . . ? C2 C3 H3 120.7 . . ? C3 C4 C5 121.6(3) . . ? C3 C4 Br1 119.6(3) . . ? C5 C4 Br1 118.8(3) . . ? C6 C5 C4 119.7(3) . . ? C6 C5 H5 120.2 . . ? C4 C5 H5 120.2 . . ? C5 C6 C1 119.5(3) . . ? C5 C6 C7 120.4(3) . . ? C1 C6 C7 120.0(3) . . ? N1 C7 C6 109.9(2) . . ? N1 C7 H7C 109.7 . . ? C6 C7 H7C 109.7 . . ? N1 C7 H7D 109.7 . . ? C6 C7 H7D 109.7 . . ? H7C C7 H7D 108.2 . . ? N1 C8 C10 113.3(2) . . ? N1 C8 C9 110.1(2) . . ? C10 C8 C9 114.7(3) . . ? N1 C8 H8 106.0 . . ? C10 C8 H8 106.0 . . ? C9 C8 H8 106.0 . . ? O3 C9 O2 124.4(3) . . ? O3 C9 C8 118.3(3) . . ? O2 C9 C8 117.3(3) . . ? C8 C10 C11 117.3(3) . . ? C8 C10 H10A 108.0 . . ? C11 C10 H10A 108.0 . . ? C8 C10 H10B 108.0 . . ? C11 C10 H10B 108.0 . . ? H10A C10 H10B 107.2 . . ? C12 C11 C13 110.5(3) . . ? C12 C11 C10 115.5(3) . . ? C13 C11 C10 108.6(3) . . ? C12 C11 H11 107.3 . . ? C13 C11 H11 107.3 . . ? C10 C11 H11 107.3 . . ? C11 C12 H12A 109.5 . . ? C11 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C11 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C11 C13 H13A 109.5 . . ? C11 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C11 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? O4 C14 C15 119.8(3) . . ? O4 C14 C19 120.8(3) . . ? C15 C14 C19 119.5(3) . . ? C16 C15 C14 121.4(3) . . ? C16 C15 H15 119.3 . . ? C14 C15 H15 119.3 . . ? C15 C16 C17 118.5(3) . . ? C15 C16 H16 120.7 . . ? C17 C16 H16 120.7 . . ? C16 C17 C18 121.5(3) . . ? C16 C17 Br2 118.8(2) . . ? C18 C17 Br2 119.6(2) . . ? C17 C18 C19 120.1(3) . . ? C17 C18 H18 119.9 . . ? C19 C18 H18 119.9 . . ? C18 C19 C14 118.8(3) . . ? C18 C19 C20 119.4(3) . . ? C14 C19 C20 121.7(3) . . ? N2 C20 C19 112.5(2) . . ? N2 C20 H20A 109.1 . . ? C19 C20 H20A 109.1 . . ? N2 C20 H20B 109.1 . . ? C19 C20 H20B 109.1 . . ? H20A C20 H20B 107.8 . . ? N2 C21 C23 114.9(2) . . ? N2 C21 C22 108.9(2) . . ? C23 C21 C22 114.4(2) . . ? N2 C21 H21 105.9 . . ? C23 C21 H21 105.9 . . ? C22 C21 H21 105.9 . . ? O6 C22 O5 123.9(3) . . ? O6 C22 C21 119.2(3) . . ? O5 C22 C21 116.8(2) . . ? C21 C23 C24 117.0(3) . . ? C21 C23 H23A 108.1 . . ? C24 C23 H23A 108.1 . . ? C21 C23 H23B 108.1 . . ? C24 C23 H23B 108.1 . . ? H23A C23 H23B 107.3 . . ? C25 C24 C26 111.1(3) . . ? C25 C24 C23 112.9(3) . . ? C26 C24 C23 108.4(3) . . ? C25 C24 H24 108.1 . . ? C26 C24 H24 108.1 . . ? C23 C24 H24 108.1 . . ? C24 C25 H25A 109.5 . . ? C24 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? C24 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? C24 C26 H26A 109.5 . . ? C24 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? C24 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? O1S S1 C1S 107.70(17) . . ? O1S S1 C2S 108.05(16) . . ? C1S S1 C2S 101.19(18) . . ? O1S S1A C2S 113.8(3) . . ? O1S S1A C1S 110.3(3) . . ? C2S S1A C1S 104.8(2) . . ? S1A O1S S1 46.55(18) . . ? S1A C1S S1 39.83(16) . . ? S1A C1S H1SA 124.0 . . ? S1 C1S H1SA 109.5 . . ? S1A C1S H1SB 123.8 . . ? S1 C1S H1SB 109.5 . . ? H1SA C1S H1SB 109.5 . . ? S1A C1S H1SC 69.6 . . ? S1 C1S H1SC 109.5 . . ? H1SA C1S H1SC 109.5 . . ? H1SB C1S H1SC 109.5 . . ? S1A C1S H1SD 109.5 . . ? S1 C1S H1SD 120.3 . . ? H1SA C1S H1SD 34.0 . . ? H1SB C1S H1SD 125.0 . . ? H1SC C1S H1SD 75.5 . . ? S1A C1S H1SE 109.5 . . ? S1 C1S H1SE 69.8 . . ? H1SA C1S H1SE 75.5 . . ? H1SB C1S H1SE 66.4 . . ? H1SC C1S H1SE 174.7 . . ? H1SD C1S H1SE 109.5 . . ? S1A C1S H1SF 109.5 . . ? S1 C1S H1SF 127.4 . . ? H1SA C1S H1SF 121.4 . . ? H1SB C1S H1SF 43.0 . . ? H1SC C1S H1SF 66.6 . . ? H1SD C1S H1SF 109.5 . . ? H1SE C1S H1SF 109.5 . . ? S1A C2S S1 40.11(16) . . ? S1A C2S H2SA 123.0 . . ? S1 C2S H2SA 109.5 . . ? S1A C2S H2SB 69.4 . . ? S1 C2S H2SB 109.5 . . ? H2SA C2S H2SB 109.5 . . ? S1A C2S H2SC 124.9 . . ? S1 C2S H2SC 109.5 . . ? H2SA C2S H2SC 109.5 . . ? H2SB C2S H2SC 109.5 . . ? S1A C2S H2SD 109.5 . . ? S1 C2S H2SD 121.3 . . ? H2SA C2S H2SD 33.7 . . ? H2SB C2S H2SD 75.8 . . ? H2SC C2S H2SD 123.9 . . ? S1A C2S H2SE 109.5 . . ? S1 C2S H2SE 126.6 . . ? H2SA C2S H2SE 122.2 . . ? H2SB C2S H2SE 66.6 . . ? H2SC C2S H2SE 43.0 . . ? H2SD C2S H2SE 109.5 . . ? S1A C2S H2SF 109.5 . . ? S1 C2S H2SF 69.5 . . ? H2SA C2S H2SF 75.8 . . ? H2SB C2S H2SF 174.5 . . ? H2SC C2S H2SF 66.5 . . ? H2SD C2S H2SF 109.5 . . ? H2SE C2S H2SF 109.5 . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O7 H7A O1S 0.842(10) 1.953(14) 2.778(3) 166(4) 2_556 O7 H7B O2 0.842(10) 2.222(14) 3.050(3) 167(4) 2_556 N2 H2 O3 0.87(4) 2.18(4) 2.809(3) 129(3) 2_556 _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 1.812 _refine_diff_density_min -1.267 _refine_diff_density_rms 0.085 #===#END _database_code_depnum_ccdc_archive 'CCDC 965515'