# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2005 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_contact_author_name 'ProfD Kumar Biradha' _publ_contact_author_address ; Department of Chemistry Indian Institute of Technology Khargapur West Bengal 721302 INDIA ; _publ_contact_author_email KBIRADHA@CHEM.IITKGP.ERNET.IN _publ_section_title ; Beta-sheet recognition in the non-interpenetrated and interpenetrated two-dimensional coordination networks containing cavities ; loop_ _publ_author_name 'Kumar Biradha' 'Madhushree Sarkar' data_mskb002b _database_code_depnum_ccdc_archive 'CCDC 253151' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C31 H31 Cl9 Cu2 I2 N8 O4' _chemical_formula_weight 1279.57 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M C2/m 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' '-x, -y, -z' 'x, -y, z' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z' _cell_length_a 9.6490(19) _cell_length_b 15.559(3) _cell_length_c 15.163(3) _cell_angle_alpha 90.00 _cell_angle_beta 91.96(3) _cell_angle_gamma 90.00 _cell_volume 2275.1(8) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 8 _cell_measurement_theta_max 14 _exptl_crystal_description 'Diamond shape' _exptl_crystal_colour 'bright yellow' _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.868 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1244 _exptl_absorpt_coefficient_mu 2.864 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 CAD4-MACH3 _diffrn_measurement_method /w-scans _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 60 _diffrn_standards_decay_% ? _diffrn_reflns_number 2064 _diffrn_reflns_av_R_equivalents 0.0353 _diffrn_reflns_av_sigmaI/netI 0.0582 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.34 _diffrn_reflns_theta_max 24.97 _reflns_number_total 1933 _reflns_number_gt 1366 _reflns_threshold_expression >2sigma(I) _computing_data_collection CAD4 _computing_cell_refinement CAD4 _computing_data_reduction CAD4 _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^)+(0.1053P)^2^+3.7223P] 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 1933 _refine_ls_number_parameters 103 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0666 _refine_ls_R_factor_gt 0.0485 _refine_ls_wR_factor_ref 0.1467 _refine_ls_wR_factor_gt 0.1277 _refine_ls_goodness_of_fit_ref 0.848 _refine_ls_restrained_S_all 0.848 _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 I1 I 0.84273(7) -0.5000 -0.11329(4) 0.0629(3) Uani 1 2 d S . . Cu1 Cu 0.89375(13) -0.5000 0.05677(7) 0.0611(4) Uani 1 2 d S . . O1 O 0.9502(4) -0.2973(4) 0.3531(3) 0.0682(13) Uani 1 1 d . . . N1 N 0.8065(6) -0.3910(3) 0.1118(3) 0.0572(13) Uani 1 1 d . . . N2 N 0.7437(5) -0.2383(4) 0.3780(3) 0.0578(13) Uani 1 1 d . . . H2 H 0.6631 -0.2259 0.3557 0.069 Uiso 1 1 calc R . . C1 C 0.7832(6) -0.2961(4) 0.2345(4) 0.0475(13) Uani 1 1 d . . . C2 C 0.8443(7) -0.3659(4) 0.1927(4) 0.0519(14) Uani 1 1 d . . . H2A H 0.9145 -0.3960 0.2228 0.062 Uiso 1 1 calc R . . C3 C 0.7083(8) -0.3437(5) 0.0681(4) 0.071(2) Uani 1 1 d . . . H3 H 0.6814 -0.3592 0.0109 0.085 Uiso 1 1 calc R . . C4 C 0.6476(9) -0.2738(6) 0.1054(4) 0.088(3) Uani 1 1 d . . . H4 H 0.5792 -0.2434 0.0739 0.106 Uiso 1 1 calc R . . C5 C 0.6870(7) -0.2482(5) 0.1888(4) 0.0637(17) Uani 1 1 d . . . H5 H 0.6490 -0.1994 0.2137 0.076 Uiso 1 1 calc R . . C6 C 0.8354(5) -0.2767(4) 0.3282(3) 0.0453(13) Uani 1 1 d . . . C7 C 0.7765(7) -0.2167(5) 0.4699(4) 0.0618(17) Uani 1 1 d . . . H7A H 0.7354 -0.1616 0.4837 0.074 Uiso 1 1 calc . . . H7B H 0.8762 -0.2116 0.4788 0.074 Uiso 1 1 calc . . . 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 I1 0.0867(5) 0.0582(4) 0.0431(4) 0.000 -0.0097(3) 0.000 Cu1 0.0923(9) 0.0449(6) 0.0459(6) 0.000 -0.0015(6) 0.000 O1 0.050(2) 0.088(4) 0.066(3) -0.009(3) -0.014(2) 0.007(2) N1 0.080(4) 0.048(3) 0.044(3) -0.010(2) 0.002(2) 0.002(3) N2 0.054(3) 0.073(4) 0.046(3) -0.012(2) -0.007(2) 0.009(3) C1 0.055(3) 0.046(3) 0.042(3) -0.002(2) 0.009(2) 0.001(3) C2 0.067(4) 0.049(3) 0.040(3) 0.005(3) 0.003(3) 0.004(3) C3 0.112(6) 0.061(4) 0.038(3) -0.004(3) -0.012(3) 0.031(4) C4 0.122(7) 0.096(6) 0.045(4) -0.006(4) -0.018(4) 0.060(5) C5 0.077(4) 0.065(4) 0.049(3) -0.005(3) -0.007(3) 0.028(4) C6 0.038(3) 0.057(3) 0.041(3) 0.000(3) 0.001(2) -0.007(3) C7 0.068(4) 0.066(4) 0.051(4) -0.020(3) -0.005(3) -0.003(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 I1 Cu1 2.6085(13) . ? I1 Cu1 2.6554(15) 5_745 ? Cu1 N1 2.081(5) 6_545 ? Cu1 N1 2.081(5) . ? Cu1 I1 2.6554(15) 5_745 ? Cu1 Cu1 2.722(3) 5_745 ? O1 C6 1.202(7) . ? N1 C2 1.326(7) . ? N1 C3 1.355(8) . ? N2 C6 1.326(7) . ? N2 C7 1.458(8) . ? C1 C5 1.361(8) . ? C1 C2 1.399(8) . ? C1 C6 1.521(8) . ? C3 C4 1.367(10) . ? C4 C5 1.367(9) . ? C7 C7 1.483(15) 7_646 ? 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 Cu1 I1 Cu1 62.27(5) . 5_745 ? N1 Cu1 N1 109.2(3) 6_545 . ? N1 Cu1 I1 109.36(14) 6_545 . ? N1 Cu1 I1 109.36(14) . . ? N1 Cu1 I1 105.47(15) 6_545 5_745 ? N1 Cu1 I1 105.47(15) . 5_745 ? I1 Cu1 I1 117.73(5) . 5_745 ? N1 Cu1 Cu1 125.29(15) 6_545 5_745 ? N1 Cu1 Cu1 125.29(15) . 5_745 ? I1 Cu1 Cu1 59.71(5) . 5_745 ? I1 Cu1 Cu1 58.02(5) 5_745 5_745 ? C2 N1 C3 117.2(5) . . ? C2 N1 Cu1 120.6(4) . . ? C3 N1 Cu1 122.2(4) . . ? C6 N2 C7 121.4(5) . . ? C5 C1 C2 119.0(6) . . ? C5 C1 C6 124.5(5) . . ? C2 C1 C6 116.5(5) . . ? N1 C2 C1 122.8(6) . . ? N1 C3 C4 122.2(6) . . ? C3 C4 C5 120.3(6) . . ? C1 C5 C4 118.4(6) . . ? O1 C6 N2 124.6(5) . . ? O1 C6 C1 120.9(5) . . ? N2 C6 C1 114.5(5) . . ? N2 C7 C7 111.0(6) . 7_646 ? _diffrn_measured_fraction_theta_max 0.928 _diffrn_reflns_theta_full 24.97 _diffrn_measured_fraction_theta_full 0.928 _refine_diff_density_max 0.793 _refine_diff_density_min -0.747 _refine_diff_density_rms 0.105 #END data_3 _database_code_depnum_ccdc_archive 'CCDC 253152' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H14 Cu2 I2 N4 O2' _chemical_formula_weight 651.17 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' I I -0.4742 1.8119 '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/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' _cell_length_a 11.312(2) _cell_length_b 10.012(2) _cell_length_c 16.597(3) _cell_angle_alpha 90.00 _cell_angle_beta 97.25(3) _cell_angle_gamma 90.00 _cell_volume 1864.7(6) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 8 _cell_measurement_theta_max 14 _exptl_crystal_description needles _exptl_crystal_colour dark-yellow _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.320 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1224 _exptl_absorpt_coefficient_mu 5.606 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.4868 _exptl_absorpt_correction_T_max 0.6041 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 CAD4-MACH3 _diffrn_measurement_method /w-scans _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 60 _diffrn_standards_decay_% 0 _diffrn_reflns_number 3247 _diffrn_reflns_av_R_equivalents 0.0632 _diffrn_reflns_av_sigmaI/netI 0.0480 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.03 _diffrn_reflns_theta_max 24.97 _reflns_number_total 3078 _reflns_number_gt 2520 _reflns_threshold_expression >2sigma(I) _computing_data_collection CAD4 _computing_cell_refinement CAD4 _computing_data_reduction CAD4 _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^)+(0.0669P)^2^+0.1392P] 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 3078 _refine_ls_number_parameters 217 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0524 _refine_ls_R_factor_gt 0.0405 _refine_ls_wR_factor_ref 0.1101 _refine_ls_wR_factor_gt 0.1003 _refine_ls_goodness_of_fit_ref 1.045 _refine_ls_restrained_S_all 1.045 _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 I1 I -0.21779(4) 0.87971(4) -0.23185(3) 0.04340(16) Uani 1 1 d . . . I2 I 0.05321(4) 0.60401(4) -0.10526(3) 0.04194(16) Uani 1 1 d . . . Cu1 Cu -0.12037(8) 0.64865(9) -0.25422(6) 0.0519(3) Uani 1 1 d . . . Cu2 Cu -0.00199(9) 0.83210(8) -0.16796(6) 0.0561(3) Uani 1 1 d . . . N1 N -0.3827(4) 0.3041(5) 0.0037(3) 0.0347(11) Uani 1 1 d . . . H1 H -0.3846 0.2288 -0.0213 0.042 Uiso 1 1 calc R . . N2 N -0.6023(4) 0.1941(5) 0.0486(3) 0.0351(11) Uani 1 1 d . . . H2 H -0.6287 0.2693 0.0289 0.042 Uiso 1 1 calc R . . C1 C -0.4122(6) 0.3085(6) 0.0855(4) 0.0386(14) Uani 1 1 d . . . H1A H -0.4530 0.3915 0.0940 0.046 Uiso 1 1 calc . . . H1B H -0.3396 0.3057 0.1235 0.046 Uiso 1 1 calc . . . C2 C -0.4917(6) 0.1908(6) 0.1014(4) 0.0389(14) Uani 1 1 d . . . H2A H -0.4505 0.1079 0.0932 0.047 Uiso 1 1 calc . . . H2B H -0.5077 0.1933 0.1575 0.047 Uiso 1 1 calc . . . O11 O -0.3497(4) 0.5242(4) -0.0031(3) 0.0419(10) Uani 1 1 d . . . C11 C -0.3207(6) 0.3955(6) -0.1201(4) 0.0389(14) Uani 1 1 d . . . C12 C -0.2634(6) 0.5008(6) -0.1517(4) 0.0433(15) Uani 1 1 d . . . H12 H -0.2476 0.5765 -0.1197 0.052 Uiso 1 1 calc R . . N11 N -0.2290(5) 0.5001(6) -0.2261(4) 0.0494(14) Uani 1 1 d . . . C13 C -0.2555(9) 0.3926(7) -0.2726(5) 0.060(2) Uani 1 1 d . . . H13 H -0.2356 0.3914 -0.3253 0.071 Uiso 1 1 calc R . . C14 C -0.3113(10) 0.2845(9) -0.2443(6) 0.085(3) Uani 1 1 d . . . H14 H -0.3281 0.2107 -0.2778 0.102 Uiso 1 1 calc R . . C15 C -0.3433(8) 0.2832(8) -0.1664(5) 0.068(2) Uani 1 1 d . . . H15 H -0.3789 0.2087 -0.1463 0.082 Uiso 1 1 calc R . . C16 C -0.3529(5) 0.4129(6) -0.0338(4) 0.0350(14) Uani 1 1 d . . . O21 O -0.6303(4) -0.0271(4) 0.0512(3) 0.0454(11) Uani 1 1 d . . . C21 C -0.7827(5) 0.1017(5) -0.0219(4) 0.0330(13) Uani 1 1 d . . . C22 C -0.8394(6) -0.0111(6) -0.0557(4) 0.0398(14) Uani 1 1 d . . . H22 H -0.8021 -0.0931 -0.0451 0.048 Uiso 1 1 calc R . . N21 N -0.9436(5) -0.0094(5) -0.1020(3) 0.0397(13) Uani 1 1 d . . . C23 C -0.9978(7) 0.1079(6) -0.1137(5) 0.0514(19) Uani 1 1 d . . . H23 H -1.0715 0.1103 -0.1456 0.062 Uiso 1 1 calc R . . C24 C -0.9518(6) 0.2250(7) -0.0816(5) 0.0538(19) Uani 1 1 d . . . H24 H -0.9932 0.3049 -0.0910 0.065 Uiso 1 1 calc R . . C25 C -0.8422(6) 0.2217(6) -0.0346(4) 0.0475(16) Uani 1 1 d . . . H25 H -0.8085 0.2998 -0.0117 0.057 Uiso 1 1 calc R . . C26 C -0.6646(5) 0.0846(6) 0.0297(4) 0.0328(13) 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 I1 0.0400(3) 0.0420(3) 0.0477(3) -0.00897(19) 0.00339(19) 0.00242(17) I2 0.0473(3) 0.0355(3) 0.0449(3) 0.00654(17) 0.0131(2) 0.00360(17) Cu1 0.0583(5) 0.0403(5) 0.0625(6) -0.0129(4) 0.0289(4) -0.0188(4) Cu2 0.0669(6) 0.0311(4) 0.0638(6) -0.0139(4) -0.0170(5) 0.0031(4) N1 0.035(3) 0.029(3) 0.041(3) 0.006(2) 0.007(2) -0.002(2) N2 0.042(3) 0.024(2) 0.038(3) 0.005(2) 0.004(2) -0.002(2) C1 0.040(3) 0.036(3) 0.038(3) -0.001(3) -0.002(3) -0.008(3) C2 0.041(3) 0.033(3) 0.045(4) 0.008(3) 0.011(3) 0.002(3) O11 0.047(2) 0.025(2) 0.055(3) -0.002(2) 0.010(2) -0.0063(18) C11 0.043(3) 0.027(3) 0.047(4) 0.008(3) 0.004(3) -0.004(2) C12 0.044(3) 0.033(3) 0.055(4) -0.012(3) 0.015(3) -0.013(3) N11 0.052(3) 0.035(3) 0.064(4) -0.006(3) 0.017(3) -0.012(3) C13 0.088(6) 0.045(4) 0.049(4) -0.004(3) 0.021(4) -0.015(4) C14 0.141(9) 0.048(5) 0.072(6) -0.023(4) 0.037(6) -0.045(6) C15 0.103(7) 0.041(4) 0.062(5) 0.002(4) 0.017(5) -0.030(4) C16 0.026(3) 0.027(3) 0.050(4) 0.002(3) -0.001(3) -0.006(2) O21 0.047(3) 0.025(2) 0.062(3) -0.002(2) 0.000(2) 0.0001(19) C21 0.038(3) 0.022(3) 0.040(3) -0.004(2) 0.009(3) -0.008(2) C22 0.038(3) 0.030(3) 0.051(4) -0.010(3) 0.007(3) -0.003(3) N21 0.045(3) 0.024(3) 0.050(3) -0.011(2) 0.005(3) -0.002(2) C23 0.054(4) 0.034(4) 0.061(5) -0.009(3) -0.013(4) 0.004(3) C24 0.049(4) 0.025(3) 0.083(5) -0.008(3) -0.009(4) 0.007(3) C25 0.058(4) 0.029(3) 0.053(4) -0.011(3) 0.000(3) -0.004(3) C26 0.039(3) 0.032(3) 0.030(3) -0.004(2) 0.013(2) -0.009(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 I1 Cu2 2.5802(12) . ? I1 Cu1 2.6090(11) . ? I2 Cu2 2.5542(11) . ? I2 Cu1 2.5814(11) 2_554 ? I2 Cu1 2.9904(15) . ? Cu1 N11 2.020(6) . ? Cu1 I2 2.5814(11) 2_554 ? Cu1 Cu2 2.5947(13) . ? Cu1 Cu1 2.7092(19) 2_554 ? Cu1 Cu2 2.7220(14) 2_554 ? Cu2 N21 1.992(5) 1_665 ? Cu2 Cu1 2.7220(14) 2_554 ? Cu2 Cu2 2.729(2) 2_554 ? N1 C16 1.320(8) . ? N1 C1 1.439(8) . ? N2 C26 1.319(7) . ? N2 C2 1.435(8) . ? C1 C2 1.526(8) . ? O11 C16 1.224(7) . ? C11 C15 1.367(10) . ? C11 C12 1.376(9) . ? C11 C16 1.531(10) . ? C12 N11 1.341(9) . ? N11 C13 1.336(9) . ? C13 C14 1.366(11) . ? C14 C15 1.386(12) . ? O21 C26 1.222(7) . ? C21 C22 1.381(8) . ? C21 C25 1.380(9) . ? C21 C26 1.503(9) . ? C22 N21 1.324(8) . ? N21 C23 1.328(8) . ? N21 Cu2 1.992(5) 1_445 ? C23 C24 1.364(9) . ? C24 C25 1.379(10) . ? 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 Cu2 I1 Cu1 60.00(3) . . ? Cu2 I2 Cu1 64.01(3) . 2_554 ? Cu2 I2 Cu1 55.13(3) . . ? Cu1 I2 Cu1 57.63(4) 2_554 . ? N11 Cu1 I2 109.74(17) . 2_554 ? N11 Cu1 Cu2 132.86(18) . . ? I2 Cu1 Cu2 115.52(4) 2_554 . ? N11 Cu1 I1 109.86(17) . . ? I2 Cu1 I1 117.38(4) 2_554 . ? Cu2 Cu1 I1 59.45(3) . . ? N11 Cu1 Cu1 128.65(18) . 2_554 ? I2 Cu1 Cu1 68.79(4) 2_554 2_554 ? Cu2 Cu1 Cu1 61.71(4) . 2_554 ? I1 Cu1 Cu1 115.63(2) . 2_554 ? N11 Cu1 Cu2 165.13(18) . 2_554 ? I2 Cu1 Cu2 57.51(3) 2_554 2_554 ? Cu2 Cu1 Cu2 61.72(5) . 2_554 ? I1 Cu1 Cu2 73.65(4) . 2_554 ? Cu1 Cu1 Cu2 57.08(3) 2_554 2_554 ? N11 Cu1 I2 93.11(18) . . ? I2 Cu1 I2 118.92(4) 2_554 . ? Cu2 Cu1 I2 53.86(3) . . ? I1 Cu1 I2 105.07(3) . . ? Cu1 Cu1 I2 53.58(4) 2_554 . ? Cu2 Cu1 I2 99.96(4) 2_554 . ? N21 Cu2 I2 116.18(16) 1_665 . ? N21 Cu2 I1 108.04(16) 1_665 . ? I2 Cu2 I1 120.17(4) . . ? N21 Cu2 Cu1 168.27(16) 1_665 . ? I2 Cu2 Cu1 71.01(4) . . ? I1 Cu2 Cu1 60.55(4) . . ? N21 Cu2 Cu1 130.15(16) 1_665 2_554 ? I2 Cu2 Cu1 58.48(3) . 2_554 ? I1 Cu2 Cu1 116.17(4) . 2_554 ? Cu1 Cu2 Cu1 61.22(5) . 2_554 ? N21 Cu2 Cu2 120.13(17) 1_665 2_554 ? I2 Cu2 Cu2 111.87(3) . 2_554 ? I1 Cu2 Cu2 73.97(5) . 2_554 ? Cu1 Cu2 Cu2 61.43(4) . 2_554 ? Cu1 Cu2 Cu2 56.85(4) 2_554 2_554 ? C16 N1 C1 121.6(5) . . ? C26 N2 C2 121.7(5) . . ? N1 C1 C2 110.6(5) . . ? N2 C2 C1 111.4(5) . . ? C15 C11 C12 118.6(7) . . ? C15 C11 C16 124.7(6) . . ? C12 C11 C16 116.6(6) . . ? N11 C12 C11 123.6(6) . . ? C13 N11 C12 117.7(6) . . ? C13 N11 Cu1 124.0(5) . . ? C12 N11 Cu1 117.7(4) . . ? N11 C13 C14 121.3(7) . . ? C13 C14 C15 121.0(8) . . ? C11 C15 C14 117.7(7) . . ? O11 C16 N1 123.4(6) . . ? O11 C16 C11 119.7(5) . . ? N1 C16 C11 116.9(5) . . ? C22 C21 C25 117.2(6) . . ? C22 C21 C26 118.1(5) . . ? C25 C21 C26 124.5(5) . . ? N21 C22 C21 124.0(6) . . ? C22 N21 C23 117.2(5) . . ? C22 N21 Cu2 121.2(4) . 1_445 ? C23 N21 Cu2 120.6(4) . 1_445 ? N21 C23 C24 123.8(7) . . ? C23 C24 C25 118.2(6) . . ? C24 C25 C21 119.5(6) . . ? O21 C26 N2 123.3(6) . . ? O21 C26 C21 119.8(5) . . ? N2 C26 C21 116.8(5) . . ? _diffrn_measured_fraction_theta_max 0.939 _diffrn_reflns_theta_full 24.97 _diffrn_measured_fraction_theta_full 0.939 _refine_diff_density_max 1.115 _refine_diff_density_min -1.075 _refine_diff_density_rms 0.153 #END data_4 _database_code_depnum_ccdc_archive 'CCDC 253153' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H22 Cu N6 O12' _chemical_formula_weight 529.92 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 P21/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 10.214(2) _cell_length_b 7.1250(14) _cell_length_c 14.425(3) _cell_angle_alpha 90.00 _cell_angle_beta 99.98(3) _cell_angle_gamma 90.00 _cell_volume 1033.9(4) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 8 _cell_measurement_theta_max 14 _exptl_crystal_description Neeldes _exptl_crystal_colour Blue _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.702 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 546 _exptl_absorpt_coefficient_mu 1.134 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.8483 _exptl_absorpt_correction_T_max 0.8950 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 CAD4-MACH3 _diffrn_measurement_method /w-scans _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 60 _diffrn_standards_decay_% 0 _diffrn_reflns_number 1922 _diffrn_reflns_av_R_equivalents 0.0213 _diffrn_reflns_av_sigmaI/netI 0.0365 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.27 _diffrn_reflns_theta_max 24.97 _reflns_number_total 1815 _reflns_number_gt 1543 _reflns_threshold_expression >2sigma(I) _computing_data_collection CAD4 _computing_cell_refinement CAD4 _computing_data_reduction CAD4 _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^)+(0.0792P)^2^+1.3528P] 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 1815 _refine_ls_number_parameters 155 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0539 _refine_ls_R_factor_gt 0.0444 _refine_ls_wR_factor_ref 0.1333 _refine_ls_wR_factor_gt 0.1187 _refine_ls_goodness_of_fit_ref 1.067 _refine_ls_restrained_S_all 1.067 _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 1.0000 0.5000 1.0000 0.0217(2) Uani 1 2 d S . . O1W O 1.1279(3) 0.7061(4) 0.93880(17) 0.0445(7) Uani 1 1 d . . . H1W H 1.1478 0.7166 0.8842 0.10(2) Uiso 1 1 d R . . H2W H 1.1426 0.8239 0.9660 0.086(18) Uiso 1 1 d R . . O2W O 0.9273(2) 0.7255(3) 1.05937(15) 0.0315(5) Uani 1 1 d . . . H3W H 0.8585 0.7031 1.0833 0.045(12) Uiso 1 1 d R . . H4W H 0.9144 0.8312 1.0320 0.060(14) Uiso 1 1 d R . . N11 N 0.8543(3) 0.5195(3) 0.88501(19) 0.0229(6) Uani 1 1 d . . . N12 N 0.9283(3) 0.5826(5) 0.60375(18) 0.0346(7) Uani 1 1 d . . . H12 H 0.9877 0.6137 0.6511 0.041 Uiso 1 1 calc R . . O11 O 0.7176(3) 0.4881(3) 0.55451(18) 0.0374(7) Uani 1 1 d . . . N100 N 0.2785(3) 0.3061(5) 0.7808(2) 0.0452(8) Uani 1 1 d . . . O101 O 0.2923(3) 0.3240(7) 0.8678(2) 0.0815(13) Uani 1 1 d . . . O102 O 0.1690(3) 0.3224(7) 0.7314(3) 0.0847(13) Uani 1 1 d . . . O103 O 0.3794(3) 0.2741(5) 0.74633(18) 0.0545(8) Uani 1 1 d . . . C11 C 0.7822(3) 0.5343(4) 0.7184(2) 0.0241(7) Uani 1 1 d . . . C12 C 0.8804(3) 0.5184(4) 0.7967(2) 0.0232(7) Uani 1 1 d . . . H12A H 0.9682 0.5066 0.7881 0.028 Uiso 1 1 calc R . . C13 C 0.7279(3) 0.5354(5) 0.8973(2) 0.0281(7) Uani 1 1 d . . . H13 H 0.7093 0.5369 0.9581 0.034 Uiso 1 1 calc R . . C14 C 0.6241(3) 0.5498(5) 0.8221(2) 0.0305(7) Uani 1 1 d . . . H14 H 0.5370 0.5609 0.8324 0.037 Uiso 1 1 calc R . . C15 C 0.6514(3) 0.5477(5) 0.7314(2) 0.0290(7) Uani 1 1 d . . . H15 H 0.5828 0.5551 0.6799 0.035 Uiso 1 1 calc R . . C16 C 0.8086(3) 0.5321(4) 0.6190(2) 0.0265(7) Uani 1 1 d . . . C17 C 0.9628(4) 0.5873(6) 0.5094(2) 0.0408(9) Uani 1 1 d . . . H17A H 1.0173 0.6967 0.5037 0.049 Uiso 1 1 calc . . . H17B H 0.8822 0.5978 0.4630 0.049 Uiso 1 1 calc . . . 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 0.0198(3) 0.0342(4) 0.0092(3) -0.00044(18) -0.0027(2) 0.00247(19) O1W 0.0574(17) 0.0535(17) 0.0225(12) -0.0025(11) 0.0069(11) -0.0207(13) O2W 0.0284(12) 0.0420(14) 0.0222(11) -0.0006(10) -0.0008(9) 0.0059(10) N11 0.0222(13) 0.0307(14) 0.0145(13) 0.0003(9) -0.0005(11) 0.0020(10) N12 0.0351(15) 0.0554(19) 0.0121(12) -0.0021(12) 0.0013(11) -0.0002(14) O11 0.0472(16) 0.0445(15) 0.0149(12) -0.0009(9) -0.0102(11) -0.0075(11) N100 0.0421(18) 0.060(2) 0.0340(16) -0.0034(15) 0.0073(14) 0.0065(16) O101 0.064(2) 0.151(4) 0.0321(16) -0.012(2) 0.0154(14) 0.016(2) O102 0.0423(17) 0.142(4) 0.065(2) -0.006(2) -0.0051(16) 0.028(2) O103 0.0395(15) 0.094(2) 0.0310(13) -0.0073(15) 0.0085(11) 0.0098(15) C11 0.0263(16) 0.0308(15) 0.0134(14) -0.0005(12) -0.0016(12) -0.0012(12) C12 0.0200(15) 0.0324(17) 0.0157(15) -0.0015(11) -0.0011(12) 0.0032(11) C13 0.0265(16) 0.0402(17) 0.0175(15) 0.0023(13) 0.0038(13) 0.0003(14) C14 0.0195(15) 0.0434(18) 0.0269(17) 0.0012(15) -0.0008(13) 0.0010(14) C15 0.0231(16) 0.0390(17) 0.0218(16) 0.0016(14) -0.0052(12) 0.0011(13) C16 0.0341(18) 0.0293(16) 0.0135(15) 0.0000(12) -0.0032(13) 0.0055(13) C17 0.044(2) 0.059(3) 0.0198(16) 0.0037(16) 0.0077(14) 0.0064(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 O2W 2.022(2) . ? Cu1 O2W 2.022(2) 3_767 ? Cu1 N11 2.032(3) 3_767 ? Cu1 N11 2.032(3) . ? Cu1 O1W 2.246(3) . ? Cu1 O1W 2.246(3) 3_767 ? N11 C13 1.338(4) . ? N11 C12 1.347(4) . ? N12 C16 1.329(5) . ? N12 C17 1.463(4) . ? O11 C16 1.236(4) . ? N100 O102 1.223(4) . ? N100 O103 1.241(4) . ? N100 O101 1.244(4) . ? C11 C12 1.379(5) . ? C11 C15 1.384(5) . ? C11 C16 1.505(4) . ? C13 C14 1.382(5) . ? C14 C15 1.385(5) . ? C17 C17 1.508(8) 3_766 ? 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 O2W Cu1 O2W 180.000(1) . 3_767 ? O2W Cu1 N11 88.81(9) . 3_767 ? O2W Cu1 N11 91.19(9) 3_767 3_767 ? O2W Cu1 N11 91.19(9) . . ? O2W Cu1 N11 88.81(9) 3_767 . ? N11 Cu1 N11 180.000(1) 3_767 . ? O2W Cu1 O1W 85.89(11) . . ? O2W Cu1 O1W 94.11(11) 3_767 . ? N11 Cu1 O1W 88.39(10) 3_767 . ? N11 Cu1 O1W 91.61(10) . . ? O2W Cu1 O1W 94.11(11) . 3_767 ? O2W Cu1 O1W 85.89(11) 3_767 3_767 ? N11 Cu1 O1W 91.61(10) 3_767 3_767 ? N11 Cu1 O1W 88.39(10) . 3_767 ? O1W Cu1 O1W 180.0 . 3_767 ? C13 N11 C12 118.6(3) . . ? C13 N11 Cu1 119.0(2) . . ? C12 N11 Cu1 122.4(2) . . ? C16 N12 C17 122.5(3) . . ? O102 N100 O103 121.5(3) . . ? O102 N100 O101 120.7(4) . . ? O103 N100 O101 117.8(3) . . ? C12 C11 C15 118.6(3) . . ? C12 C11 C16 123.6(3) . . ? C15 C11 C16 117.8(3) . . ? N11 C12 C11 122.6(3) . . ? N11 C13 C14 122.0(3) . . ? C15 C14 C13 119.2(3) . . ? C14 C15 C11 119.0(3) . . ? O11 C16 N12 122.5(3) . . ? O11 C16 C11 119.0(3) . . ? N12 C16 C11 118.5(3) . . ? N12 C17 C17 111.1(4) . 3_766 ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 24.97 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.416 _refine_diff_density_min -1.411 _refine_diff_density_rms 0.136 #END