# Electronic Supplementary Material (ESI) for RSC Advances # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # 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_1 #TrackingRef 'compounds.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C24 H16 Ag In N4 O8' _chemical_formula_weight 711.10 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' Ag Ag -0.8971 1.1015 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' In In -0.7276 1.3100 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Fddd loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+3/4, -y+3/4, z' '-x+3/4, y, -z+3/4' 'x, -y+3/4, -z+3/4' 'x, y+1/2, z+1/2' '-x+3/4, -y+5/4, z+1/2' '-x+3/4, y+1/2, -z+5/4' 'x, -y+5/4, -z+5/4' 'x+1/2, y, z+1/2' '-x+5/4, -y+3/4, z+1/2' '-x+5/4, y, -z+5/4' 'x+1/2, -y+3/4, -z+5/4' 'x+1/2, y+1/2, z' '-x+5/4, -y+5/4, z' '-x+5/4, y+1/2, -z+3/4' 'x+1/2, -y+5/4, -z+3/4' '-x, -y, -z' 'x-3/4, y-3/4, -z' 'x-3/4, -y, z-3/4' '-x, y-3/4, z-3/4' '-x, -y+1/2, -z+1/2' 'x-3/4, y-1/4, -z+1/2' 'x-3/4, -y+1/2, z-1/4' '-x, y-1/4, z-1/4' '-x+1/2, -y, -z+1/2' 'x-1/4, y-3/4, -z+1/2' 'x-1/4, -y, z-1/4' '-x+1/2, y-3/4, z-1/4' '-x+1/2, -y+1/2, -z' 'x-1/4, y-1/4, -z' 'x-1/4, -y+1/2, z-3/4' '-x+1/2, y-1/4, z-3/4' _cell_length_a 12.0412(8) _cell_length_b 23.6221(17) _cell_length_c 25.381(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 7219.2(9) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1066 _cell_measurement_theta_min 3.0603 _cell_measurement_theta_max 26.4348 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max .25 _exptl_crystal_size_mid .20 _exptl_crystal_size_min .20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.309 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2784 _exptl_absorpt_coefficient_mu 1.221 _exptl_absorpt_correction_T_min 0.74999 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET) (compiled Jan 20 2011,15:58:25) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Xcalibur, Eos' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean none _diffrn_standards_number none _diffrn_standards_interval_count none _diffrn_standards_interval_time none _diffrn_standards_decay_% none _diffrn_reflns_number 3389 _diffrn_reflns_av_R_equivalents 0.0340 _diffrn_reflns_av_sigmaI/netI 0.0350 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -25 _diffrn_reflns_limit_k_max 26 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_theta_min 3.07 _diffrn_reflns_theta_max 24.99 _reflns_number_total 1456 _reflns_number_gt 993 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker FRAMBO' _computing_cell_refinement 'Bruker FRAMBO' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1202P)^2^+59.6590P] 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 none _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1456 _refine_ls_number_parameters 88 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0784 _refine_ls_R_factor_gt 0.0614 _refine_ls_wR_factor_ref 0.2261 _refine_ls_wR_factor_gt 0.2028 _refine_ls_goodness_of_fit_ref 1.084 _refine_ls_restrained_S_all 1.084 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N1 N -0.0470(5) -0.0600(3) 0.3184(3) 0.0762(19) Uani 1 1 d . . . Ag1 Ag -0.1250 -0.1250 0.3750 0.0687(6) Uani 1 4 d S . . In1 In 0.1250 0.1250 0.1250 0.0475(5) Uani 1 4 d S . . O1 O 0.1557(4) 0.0563(2) 0.1862(2) 0.0737(16) Uani 1 1 d . . . O2 O -0.0153(4) 0.08147(19) 0.17050(19) 0.0665(14) Uani 1 1 d . . . C1 C -0.0855(7) 0.0150(4) 0.2585(3) 0.082(3) Uani 1 1 d . . . H1A H -0.1364 0.0409 0.2452 0.099 Uiso 1 1 calc R . . C2 C 0.0907(7) -0.0273(3) 0.2593(4) 0.077(2) Uani 1 1 d . . . H2A H 0.1631 -0.0300 0.2469 0.092 Uiso 1 1 calc R . . C3 C -0.1160(6) -0.0211(5) 0.2987(4) 0.098(4) Uani 1 1 d . . . H3A H -0.1873 -0.0182 0.3125 0.117 Uiso 1 1 calc R . . C4 C 0.0550(6) -0.0631(3) 0.2984(3) 0.080(2) Uani 1 1 d . . . H4A H 0.1036 -0.0904 0.3113 0.097 Uiso 1 1 calc R . . C5 C 0.0563(7) 0.0518(3) 0.1953(3) 0.0605(18) Uani 1 1 d . . . C6 C 0.0193(5) 0.0127(3) 0.2383(3) 0.0574(17) 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 N1 0.065(4) 0.086(4) 0.078(4) 0.034(4) 0.006(3) 0.001(3) Ag1 0.1128(12) 0.0471(8) 0.0462(8) 0.000 0.000 0.000 In1 0.0494(7) 0.0465(7) 0.0467(7) 0.000 0.000 0.000 O1 0.048(3) 0.084(4) 0.090(4) 0.022(3) 0.001(3) -0.003(3) O2 0.060(3) 0.069(3) 0.070(3) 0.016(3) 0.003(2) 0.015(2) C1 0.055(4) 0.100(6) 0.091(6) 0.050(5) 0.010(4) 0.011(4) C2 0.054(4) 0.069(5) 0.108(7) 0.037(5) 0.015(4) 0.014(4) C3 0.048(5) 0.141(9) 0.104(7) 0.064(7) 0.022(4) 0.031(5) C4 0.059(5) 0.081(5) 0.101(6) 0.028(5) 0.003(4) 0.013(4) C5 0.080(5) 0.048(4) 0.053(4) 0.002(3) 0.018(4) -0.002(4) C6 0.051(4) 0.061(4) 0.060(4) 0.016(3) 0.003(3) 0.006(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C4 1.331(9) . ? N1 C3 1.337(10) . ? N1 Ag1 2.303(6) . ? Ag1 N1 2.303(6) 2_445 ? Ag1 N1 2.303(6) 3_455 ? Ag1 N1 2.303(6) 4_545 ? In1 O1 2.276(5) 11_454 ? In1 O1 2.276(5) 14_445 ? In1 O1 2.276(5) . ? In1 O1 2.276(5) 8_544 ? In1 O2 2.290(5) 14_445 ? In1 O2 2.290(5) . ? In1 O2 2.290(5) 11_454 ? In1 O2 2.290(5) 8_544 ? In1 C5 2.620(7) 14_445 ? In1 C5 2.620(7) 11_454 ? In1 C5 2.620(7) 8_544 ? In1 C5 2.620(7) . ? O1 C5 1.225(9) . ? O2 C5 1.277(8) . ? C1 C6 1.363(10) . ? C1 C3 1.378(11) . ? C1 H1A 0.9300 . ? C2 C4 1.372(10) . ? C2 C6 1.384(9) . ? C2 H2A 0.9300 . ? C3 H3A 0.9300 . ? C4 H4A 0.9300 . ? C5 C6 1.497(9) . ? 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 C4 N1 C3 117.9(7) . . ? C4 N1 Ag1 125.3(5) . . ? C3 N1 Ag1 116.0(5) . . ? N1 Ag1 N1 131.9(3) 2_445 3_455 ? N1 Ag1 N1 96.4(3) 2_445 4_545 ? N1 Ag1 N1 102.8(4) 3_455 4_545 ? N1 Ag1 N1 102.8(4) 2_445 . ? N1 Ag1 N1 96.4(3) 3_455 . ? N1 Ag1 N1 131.9(3) 4_545 . ? O1 In1 O1 161.3(3) 11_454 14_445 ? O1 In1 O1 89.1(3) 11_454 . ? O1 In1 O1 93.9(3) 14_445 . ? O1 In1 O1 93.9(3) 11_454 8_544 ? O1 In1 O1 89.1(3) 14_445 8_544 ? O1 In1 O1 161.3(3) . 8_544 ? O1 In1 O2 141.63(17) 11_454 14_445 ? O1 In1 O2 57.03(17) 14_445 14_445 ? O1 In1 O2 81.72(18) . 14_445 ? O1 In1 O2 84.51(18) 8_544 14_445 ? O1 In1 O2 84.51(18) 11_454 . ? O1 In1 O2 81.72(18) 14_445 . ? O1 In1 O2 57.03(17) . . ? O1 In1 O2 141.63(17) 8_544 . ? O2 In1 O2 119.4(2) 14_445 . ? O1 In1 O2 57.03(17) 11_454 11_454 ? O1 In1 O2 141.63(17) 14_445 11_454 ? O1 In1 O2 84.51(18) . 11_454 ? O1 In1 O2 81.72(18) 8_544 11_454 ? O2 In1 O2 84.9(2) 14_445 11_454 ? O2 In1 O2 126.6(2) . 11_454 ? O1 In1 O2 81.72(18) 11_454 8_544 ? O1 In1 O2 84.51(18) 14_445 8_544 ? O1 In1 O2 141.63(17) . 8_544 ? O1 In1 O2 57.03(17) 8_544 8_544 ? O2 In1 O2 126.6(2) 14_445 8_544 ? O2 In1 O2 84.9(2) . 8_544 ? O2 In1 O2 119.4(2) 11_454 8_544 ? O1 In1 C5 170.7(2) 11_454 14_445 ? O1 In1 C5 27.9(2) 14_445 14_445 ? O1 In1 C5 87.4(2) . 14_445 ? O1 In1 C5 86.7(2) 8_544 14_445 ? O2 In1 C5 29.2(2) 14_445 14_445 ? O2 In1 C5 100.7(2) . 14_445 ? O2 In1 C5 114.0(2) 11_454 14_445 ? O2 In1 C5 106.3(2) 8_544 14_445 ? O1 In1 C5 27.9(2) 11_454 11_454 ? O1 In1 C5 170.7(2) 14_445 11_454 ? O1 In1 C5 86.7(2) . 11_454 ? O1 In1 C5 87.4(2) 8_544 11_454 ? O2 In1 C5 114.0(2) 14_445 11_454 ? O2 In1 C5 106.3(2) . 11_454 ? O2 In1 C5 29.2(2) 11_454 11_454 ? O2 In1 C5 100.7(2) 8_544 11_454 ? C5 In1 C5 143.2(4) 14_445 11_454 ? O1 In1 C5 87.4(2) 11_454 8_544 ? O1 In1 C5 86.7(2) 14_445 8_544 ? O1 In1 C5 170.7(2) . 8_544 ? O1 In1 C5 27.9(2) 8_544 8_544 ? O2 In1 C5 106.3(2) 14_445 8_544 ? O2 In1 C5 114.0(2) . 8_544 ? O2 In1 C5 100.7(2) 11_454 8_544 ? O2 In1 C5 29.2(2) 8_544 8_544 ? C5 In1 C5 97.4(3) 14_445 8_544 ? C5 In1 C5 94.1(3) 11_454 8_544 ? O1 In1 C5 86.7(2) 11_454 . ? O1 In1 C5 87.4(2) 14_445 . ? O1 In1 C5 27.9(2) . . ? O1 In1 C5 170.7(2) 8_544 . ? O2 In1 C5 100.7(2) 14_445 . ? O2 In1 C5 29.2(2) . . ? O2 In1 C5 106.3(2) 11_454 . ? O2 In1 C5 114.0(2) 8_544 . ? C5 In1 C5 94.1(3) 14_445 . ? C5 In1 C5 97.4(3) 11_454 . ? C5 In1 C5 143.2(4) 8_544 . ? C5 O1 In1 91.9(4) . . ? C5 O2 In1 89.9(4) . . ? C6 C1 C3 120.0(7) . . ? C6 C1 H1A 120.0 . . ? C3 C1 H1A 120.0 . . ? C4 C2 C6 120.3(7) . . ? C4 C2 H2A 119.8 . . ? C6 C2 H2A 119.8 . . ? N1 C3 C1 122.4(7) . . ? N1 C3 H3A 118.8 . . ? C1 C3 H3A 118.8 . . ? N1 C4 C2 122.1(7) . . ? N1 C4 H4A 119.0 . . ? C2 C4 H4A 119.0 . . ? O1 C5 O2 121.2(6) . . ? O1 C5 C6 118.9(7) . . ? O2 C5 C6 119.9(7) . . ? O1 C5 In1 60.3(4) . . ? O2 C5 In1 61.0(3) . . ? C6 C5 In1 176.2(5) . . ? C1 C6 C2 117.2(7) . . ? C1 C6 C5 121.6(6) . . ? C2 C6 C5 121.2(7) . . ? loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons 1 -0.040 0.125 0.875 359.4 6.6 2 -0.039 0.125 0.375 359.4 6.6 3 0.017 0.375 0.125 359.4 6.3 4 0.020 0.375 0.625 359.4 6.3 5 -0.040 0.625 0.375 359.4 6.6 6 -0.039 0.625 0.875 359.4 6.6 7 0.017 0.875 0.625 359.4 6.3 8 0.020 0.875 0.125 359.4 6.3 _diffrn_measured_fraction_theta_max 0.910 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 0.910 _refine_diff_density_max 1.018 _refine_diff_density_min -0.950 _refine_diff_density_rms 0.118 _database_code_depnum_ccdc_archive 'CCDC 902245' ####################################################################### # # 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_2 #TrackingRef 'compounds.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C24 H16 Cu In N4 O8' _chemical_formula_weight 666.77 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' In In -0.7276 1.3100 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Fddd loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+3/4, -y+3/4, z' '-x+3/4, y, -z+3/4' 'x, -y+3/4, -z+3/4' 'x, y+1/2, z+1/2' '-x+3/4, -y+5/4, z+1/2' '-x+3/4, y+1/2, -z+5/4' 'x, -y+5/4, -z+5/4' 'x+1/2, y, z+1/2' '-x+5/4, -y+3/4, z+1/2' '-x+5/4, y, -z+5/4' 'x+1/2, -y+3/4, -z+5/4' 'x+1/2, y+1/2, z' '-x+5/4, -y+5/4, z' '-x+5/4, y+1/2, -z+3/4' 'x+1/2, -y+5/4, -z+3/4' '-x, -y, -z' 'x-3/4, y-3/4, -z' 'x-3/4, -y, z-3/4' '-x, y-3/4, z-3/4' '-x, -y+1/2, -z+1/2' 'x-3/4, y-1/4, -z+1/2' 'x-3/4, -y+1/2, z-1/4' '-x, y-1/4, z-1/4' '-x+1/2, -y, -z+1/2' 'x-1/4, y-3/4, -z+1/2' 'x-1/4, -y, z-1/4' '-x+1/2, y-3/4, z-1/4' '-x+1/2, -y+1/2, -z' 'x-1/4, y-1/4, -z' 'x-1/4, -y+1/2, z-3/4' '-x+1/2, y-1/4, z-3/4' _cell_length_a 12.4623(7) _cell_length_b 22.5494(9) _cell_length_c 24.692(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 6938.8(7) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 987 _cell_measurement_theta_min 3.0603 _cell_measurement_theta_max 26.4348 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max .25 _exptl_crystal_size_mid .20 _exptl_crystal_size_min .20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.277 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2640 _exptl_absorpt_coefficient_mu 1.318 _exptl_absorpt_correction_T_min 0.74999 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET) (compiled Jan 20 2011,15:58:25) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Xcalibur, Eos' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean none _diffrn_standards_number none _diffrn_standards_interval_count none _diffrn_standards_interval_time none _diffrn_standards_decay_% none _diffrn_reflns_number 4173 _diffrn_reflns_av_R_equivalents 0.0334 _diffrn_reflns_av_sigmaI/netI 0.0330 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -26 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_theta_min 2.45 _diffrn_reflns_theta_max 25.00 _reflns_number_total 1534 _reflns_number_gt 1174 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0949P)^2^+70.4023P] 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 none _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1534 _refine_ls_number_parameters 88 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0667 _refine_ls_R_factor_gt 0.0539 _refine_ls_wR_factor_ref 0.2098 _refine_ls_wR_factor_gt 0.1978 _refine_ls_goodness_of_fit_ref 1.288 _refine_ls_restrained_S_all 1.288 _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 In1 In 0.1250 0.1250 0.1250 0.0319(4) Uani 1 4 d S . . Cu1 Cu -0.1250 -0.1250 0.3750 0.0438(5) Uani 1 4 d S . . O1 O 0.1562(5) 0.0536(3) 0.1883(2) 0.0643(15) Uani 1 1 d . . . O2 O -0.0107(4) 0.0786(2) 0.1708(2) 0.0548(13) Uani 1 1 d . . . N1 N -0.0502(5) -0.0659(3) 0.3219(2) 0.0518(15) Uani 1 1 d . . . C1 C -0.0846(7) 0.0109(4) 0.2591(3) 0.067(2) Uani 1 1 d . . . H1A H -0.1334 0.0374 0.2440 0.081 Uiso 1 1 calc R . . C2 C 0.0887(6) -0.0311(4) 0.2646(3) 0.063(2) Uani 1 1 d . . . H2A H 0.1600 -0.0333 0.2537 0.076 Uiso 1 1 calc R . . C3 C -0.1161(6) -0.0267(5) 0.2996(4) 0.075(3) Uani 1 1 d . . . H3A H -0.1865 -0.0247 0.3120 0.090 Uiso 1 1 calc R . . C4 C 0.0497(6) -0.0681(4) 0.3051(4) 0.065(2) Uani 1 1 d . . . H4A H 0.0960 -0.0955 0.3208 0.078 Uiso 1 1 calc R . . C5 C 0.0588(6) 0.0497(3) 0.1972(3) 0.0452(16) Uani 1 1 d . . . C6 C 0.0192(6) 0.0092(3) 0.2408(3) 0.0520(18) 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 In1 0.0386(6) 0.0301(6) 0.0270(6) 0.000 0.000 0.000 Cu1 0.0685(13) 0.0343(9) 0.0287(9) 0.000 0.000 0.000 O1 0.055(3) 0.075(4) 0.062(4) 0.019(3) 0.010(3) 0.006(3) O2 0.063(3) 0.056(3) 0.045(3) 0.015(2) 0.010(2) 0.011(2) N1 0.055(4) 0.051(3) 0.050(4) 0.018(3) 0.007(3) 0.009(3) C1 0.056(5) 0.077(6) 0.069(5) 0.045(5) 0.009(4) 0.020(4) C2 0.048(4) 0.071(5) 0.071(5) 0.023(5) 0.019(4) 0.018(4) C3 0.052(5) 0.093(7) 0.080(7) 0.045(6) 0.014(4) 0.019(4) C4 0.059(5) 0.057(5) 0.079(6) 0.024(4) 0.009(4) 0.019(4) C5 0.057(4) 0.039(4) 0.040(4) 0.010(3) 0.006(3) 0.006(3) C6 0.052(4) 0.057(4) 0.048(4) 0.016(4) 0.008(3) 0.011(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 In1 O1 2.278(6) 11_454 ? In1 O1 2.278(6) 14_445 ? In1 O1 2.278(6) 8_544 ? In1 O1 2.278(6) . ? In1 O2 2.288(5) 14_445 ? In1 O2 2.288(5) . ? In1 O2 2.288(5) 11_454 ? In1 O2 2.288(5) 8_544 ? In1 C5 2.596(6) 14_445 ? In1 C5 2.596(6) 11_454 ? In1 C5 2.596(6) 8_544 ? In1 C5 2.596(6) . ? Cu1 N1 2.089(6) 2_445 ? Cu1 N1 2.089(6) 3_455 ? Cu1 N1 2.089(6) 4_545 ? Cu1 N1 2.089(6) . ? O1 C5 1.236(9) . ? O2 C5 1.265(8) . ? N1 C4 1.313(10) . ? N1 C3 1.326(9) . ? C1 C3 1.370(11) . ? C1 C6 1.371(10) . ? C1 H1A 0.9300 . ? C2 C6 1.387(10) . ? C2 C4 1.391(11) . ? C2 H2A 0.9300 . ? C3 H3A 0.9300 . ? C4 H4A 0.9300 . ? C5 C6 1.495(9) . ? 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 In1 O1 160.4(3) 11_454 14_445 ? O1 In1 O1 93.3(3) 11_454 8_544 ? O1 In1 O1 90.0(3) 14_445 8_544 ? O1 In1 O1 90.0(3) 11_454 . ? O1 In1 O1 93.3(3) 14_445 . ? O1 In1 O1 160.4(3) 8_544 . ? O1 In1 O2 142.06(19) 11_454 14_445 ? O1 In1 O2 57.55(19) 14_445 14_445 ? O1 In1 O2 83.72(19) 8_544 14_445 ? O1 In1 O2 81.8(2) . 14_445 ? O1 In1 O2 83.72(19) 11_454 . ? O1 In1 O2 81.8(2) 14_445 . ? O1 In1 O2 142.06(19) 8_544 . ? O1 In1 O2 57.55(19) . . ? O2 In1 O2 120.7(3) 14_445 . ? O1 In1 O2 57.55(19) 11_454 11_454 ? O1 In1 O2 142.06(19) 14_445 11_454 ? O1 In1 O2 81.8(2) 8_544 11_454 ? O1 In1 O2 83.72(19) . 11_454 ? O2 In1 O2 84.7(2) 14_445 11_454 ? O2 In1 O2 125.6(2) . 11_454 ? O1 In1 O2 81.8(2) 11_454 8_544 ? O1 In1 O2 83.72(19) 14_445 8_544 ? O1 In1 O2 57.55(19) 8_544 8_544 ? O1 In1 O2 142.06(19) . 8_544 ? O2 In1 O2 125.6(2) 14_445 8_544 ? O2 In1 O2 84.7(2) . 8_544 ? O2 In1 O2 120.7(3) 11_454 8_544 ? O1 In1 C5 171.0(2) 11_454 14_445 ? O1 In1 C5 28.4(2) 14_445 14_445 ? O1 In1 C5 87.4(2) 8_544 14_445 ? O1 In1 C5 86.4(2) . 14_445 ? O2 In1 C5 29.2(2) 14_445 14_445 ? O2 In1 C5 101.2(2) . 14_445 ? O2 In1 C5 113.8(2) 11_454 14_445 ? O2 In1 C5 106.0(2) 8_544 14_445 ? O1 In1 C5 28.4(2) 11_454 11_454 ? O1 In1 C5 171.0(2) 14_445 11_454 ? O1 In1 C5 86.4(2) 8_544 11_454 ? O1 In1 C5 87.4(2) . 11_454 ? O2 In1 C5 113.8(2) 14_445 11_454 ? O2 In1 C5 106.0(2) . 11_454 ? O2 In1 C5 29.2(2) 11_454 11_454 ? O2 In1 C5 101.2(2) 8_544 11_454 ? C5 In1 C5 143.0(3) 14_445 11_454 ? O1 In1 C5 86.4(2) 11_454 8_544 ? O1 In1 C5 87.4(2) 14_445 8_544 ? O1 In1 C5 28.4(2) 8_544 8_544 ? O1 In1 C5 171.0(2) . 8_544 ? O2 In1 C5 106.0(2) 14_445 8_544 ? O2 In1 C5 113.8(2) . 8_544 ? O2 In1 C5 101.2(2) 11_454 8_544 ? O2 In1 C5 29.2(2) 8_544 8_544 ? C5 In1 C5 98.3(3) 14_445 8_544 ? C5 In1 C5 93.3(3) 11_454 8_544 ? O1 In1 C5 87.4(2) 11_454 . ? O1 In1 C5 86.4(2) 14_445 . ? O1 In1 C5 171.0(2) 8_544 . ? O1 In1 C5 28.4(2) . . ? O2 In1 C5 101.2(2) 14_445 . ? O2 In1 C5 29.2(2) . . ? O2 In1 C5 106.0(2) 11_454 . ? O2 In1 C5 113.8(2) 8_544 . ? C5 In1 C5 93.3(3) 14_445 . ? C5 In1 C5 98.3(3) 11_454 . ? C5 In1 C5 143.0(3) 8_544 . ? N1 Cu1 N1 127.0(3) 2_445 3_455 ? N1 Cu1 N1 100.7(3) 2_445 4_545 ? N1 Cu1 N1 102.2(4) 3_455 4_545 ? N1 Cu1 N1 102.2(4) 2_445 . ? N1 Cu1 N1 100.7(3) 3_455 . ? N1 Cu1 N1 127.0(3) 4_545 . ? C5 O1 In1 90.2(4) . . ? C5 O2 In1 89.1(4) . . ? C4 N1 C3 118.8(7) . . ? C4 N1 Cu1 126.7(5) . . ? C3 N1 Cu1 114.1(5) . . ? C3 C1 C6 119.6(7) . . ? C3 C1 H1A 120.2 . . ? C6 C1 H1A 120.2 . . ? C6 C2 C4 118.7(7) . . ? C6 C2 H2A 120.7 . . ? C4 C2 H2A 120.7 . . ? N1 C3 C1 122.6(7) . . ? N1 C3 H3A 118.7 . . ? C1 C3 H3A 118.7 . . ? N1 C4 C2 122.4(7) . . ? N1 C4 H4A 118.8 . . ? C2 C4 H4A 118.8 . . ? O1 C5 O2 123.0(6) . . ? O1 C5 C6 119.7(6) . . ? O2 C5 C6 117.3(6) . . ? O1 C5 In1 61.3(4) . . ? O2 C5 In1 61.8(3) . . ? C6 C5 In1 176.8(5) . . ? C1 C6 C2 117.9(7) . . ? C1 C6 C5 122.2(6) . . ? C2 C6 C5 119.9(7) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.506 _refine_diff_density_min -0.570 _refine_diff_density_rms 0.119 #end _database_code_depnum_ccdc_archive 'CCDC 902246'