# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full CrystEngComm _journal_coden_cambridge 1350 _journal_year ? _journal_volume ? _journal_page_first ? loop_ _publ_author_name T.Maji S.Mohapatra S.Kitagawa R.Matsuda H.Sato _publ_contact_author_name 'Tapas Maji' _publ_contact_author_email tmaji@jncasr.ac.in #=====END data_compound_2 _database_code_depnum_ccdc_archive 'CCDC 859368' #TrackingRef '- mcif.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C6 H2 Cu2 N2 O5' _chemical_formula_weight 309.18 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' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 19.3929(10) _cell_length_b 12.5914(6) _cell_length_c 7.5890(3) _cell_angle_alpha 90.00 _cell_angle_beta 107.013(2) _cell_angle_gamma 90.00 _cell_volume 1772.02(14) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description Block _exptl_crystal_colour red _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.318 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1200 _exptl_absorpt_coefficient_mu 4.800 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.7564 _exptl_absorpt_correction_T_max 0.9981 _exptl_absorpt_process_details SADABS _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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7089 _diffrn_reflns_av_R_equivalents 0.0652 _diffrn_reflns_av_sigmaI/netI 0.0594 _diffrn_reflns_limit_h_min -24 _diffrn_reflns_limit_h_max 24 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -6 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 1.95 _diffrn_reflns_theta_max 26.58 _reflns_number_total 1853 _reflns_number_gt 1391 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker,2000)' _computing_cell_refinement SMART _computing_data_reduction 'SAINT (Bruker,2000)' _computing_structure_solution 'SIR-92 (Altomare et al. 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Mercury 1.4.1' _computing_publication_material 'PLATON (Spek, 2003)' _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^)+(0.1364P)^2^+6.8274P] 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 noref _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1853 _refine_ls_number_parameters 138 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0918 _refine_ls_R_factor_gt 0.0697 _refine_ls_wR_factor_ref 0.1991 _refine_ls_wR_factor_gt 0.1771 _refine_ls_goodness_of_fit_ref 0.997 _refine_ls_restrained_S_all 0.997 _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 0.20535(4) 0.68377(6) 0.27827(11) 0.0218(3) Uani 1 1 d . . . Cu2 Cu 0.0000 0.62914(15) -0.2500 0.0564(5) Uani 1 2 d S . . Cu3 Cu 0.0000 0.30281(14) -0.2500 0.0592(5) Uani 1 2 d S . . O1 O 0.1092(2) 0.6145(3) 0.0829(6) 0.0231(10) Uani 1 1 d . . . O2 O 0.0716(2) 0.4540(4) -0.0292(7) 0.0296(11) Uani 1 1 d . . . O3 O 0.1500(2) 0.2441(3) -0.0568(6) 0.0219(9) Uani 1 1 d . . . O4 O 0.1003(3) 0.2411(4) 0.1762(7) 0.0376(12) Uani 1 1 d . . . N1 N 0.2322(2) 0.5342(4) 0.3095(6) 0.0161(10) Uani 1 1 d . . . N2 N 0.2617(3) 0.3179(4) 0.3020(6) 0.0176(11) Uani 1 1 d . . . C1 C 0.2946(3) 0.4935(5) 0.4161(8) 0.0246(14) Uani 1 1 d . . . H1 H 0.3283 0.5376 0.4948 0.030 Uiso 1 1 calc R . . C2 C 0.3089(3) 0.3852(5) 0.4089(8) 0.0232(14) Uani 1 1 d . . . H2 H 0.3529 0.3590 0.4814 0.028 Uiso 1 1 calc R . . C3 C 0.1972(3) 0.3581(5) 0.1986(8) 0.0165(12) Uani 1 1 d . . . C4 C 0.1831(3) 0.4646(4) 0.1982(7) 0.0128(11) Uani 1 1 d . . . C5 C 0.1161(3) 0.5158(5) 0.0742(7) 0.0159(12) Uani 1 1 d . . . C6 C 0.1441(3) 0.2746(5) 0.0945(8) 0.0179(12) Uani 1 1 d . . . O1W O -0.0002(6) 0.1038(9) -0.050(2) 0.185(8) 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 0.0200(5) 0.0094(5) 0.0325(5) -0.0012(3) 0.0022(3) -0.0038(3) Cu2 0.0485(10) 0.0654(12) 0.0514(9) 0.000 0.0085(7) 0.000 Cu3 0.0585(11) 0.0543(11) 0.0568(10) 0.000 0.0044(8) 0.000 O1 0.022(2) 0.008(2) 0.030(2) 0.0012(17) -0.0065(17) 0.0007(16) O2 0.019(2) 0.018(2) 0.042(3) -0.009(2) -0.0075(19) 0.0047(18) O3 0.025(2) 0.017(2) 0.022(2) -0.0049(17) 0.0041(17) -0.0051(18) O4 0.041(3) 0.029(3) 0.050(3) -0.013(2) 0.025(2) -0.013(2) N1 0.016(2) 0.011(2) 0.019(2) -0.0030(19) 0.0019(19) -0.0040(19) N2 0.020(3) 0.015(3) 0.017(2) 0.0048(19) 0.0035(19) 0.0033(19) C1 0.028(3) 0.012(3) 0.027(3) -0.006(2) -0.004(3) 0.002(3) C2 0.019(3) 0.021(3) 0.021(3) -0.001(2) -0.009(2) 0.009(2) C3 0.018(3) 0.011(3) 0.022(3) -0.004(2) 0.008(2) -0.006(2) C4 0.008(2) 0.011(3) 0.015(2) -0.001(2) -0.002(2) 0.001(2) C5 0.013(3) 0.014(3) 0.018(3) 0.001(2) 0.000(2) 0.007(2) C6 0.015(3) 0.010(3) 0.028(3) -0.003(2) 0.004(2) -0.004(2) O1W 0.108(8) 0.124(10) 0.247(17) 0.092(10) -0.068(10) -0.060(7) _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 N1 1.949(5) . ? Cu1 N2 1.964(5) 4 ? Cu1 O3 2.081(4) 6_566 ? Cu1 O1 2.195(4) . ? O1 C5 1.254(7) . ? O2 C5 1.252(7) . ? O3 C6 1.247(7) . ? O3 Cu1 2.081(4) 6_565 ? O4 C6 1.263(8) . ? N1 C1 1.344(7) . ? N1 C4 1.385(6) . ? N2 C2 1.333(8) . ? N2 C3 1.366(7) . ? N2 Cu1 1.964(5) 4_545 ? C1 C2 1.396(8) . ? C1 H1 0.9300 . ? C2 H2 0.9300 . ? C3 C4 1.368(8) . ? C3 C6 1.521(8) . ? C4 C5 1.508(7) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 Cu1 N2 140.2(2) . 4 ? N1 Cu1 O3 120.98(18) . 6_566 ? N2 Cu1 O3 94.75(19) 4 6_566 ? N1 Cu1 O1 80.92(16) . . ? N2 Cu1 O1 114.92(18) 4 . ? O3 Cu1 O1 95.39(17) 6_566 . ? C5 O1 Cu1 110.3(3) . . ? C6 O3 Cu1 128.4(4) . 6_565 ? C1 N1 C4 117.5(5) . . ? C1 N1 Cu1 127.1(4) . . ? C4 N1 Cu1 115.2(3) . . ? C2 N2 C3 117.7(5) . . ? C2 N2 Cu1 120.5(4) . 4_545 ? C3 N2 Cu1 117.9(4) . 4_545 ? N1 C1 C2 120.2(5) . . ? N1 C1 H1 119.9 . . ? C2 C1 H1 119.9 . . ? N2 C2 C1 122.4(5) . . ? N2 C2 H2 118.8 . . ? C1 C2 H2 118.8 . . ? N2 C3 C4 120.9(5) . . ? N2 C3 C6 114.1(5) . . ? C4 C3 C6 124.9(5) . . ? C3 C4 N1 121.2(5) . . ? C3 C4 C5 123.7(5) . . ? N1 C4 C5 115.1(5) . . ? O1 C5 O2 125.8(5) . . ? O1 C5 C4 118.4(5) . . ? O2 C5 C4 115.8(5) . . ? O3 C6 O4 127.2(5) . . ? O3 C6 C3 117.5(5) . . ? O4 C6 C3 115.2(5) . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 26.58 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 1.241 _refine_diff_density_min -1.625 _refine_diff_density_rms 0.242 #===END data_compound1' _database_code_depnum_ccdc_archive 'CCDC 859369' #TrackingRef '- mcif.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C6 H2 Cu2 N2 O4' _chemical_formula_weight 293.18 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' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 19.3848(4) _cell_length_b 12.5209(2) _cell_length_c 7.7134(2) _cell_angle_alpha 90.00 _cell_angle_beta 107.8220(10) _cell_angle_gamma 90.00 _cell_volume 1782.32(7) _cell_formula_units_Z 8 _cell_measurement_temperature 455(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description Block _exptl_crystal_colour red _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.185 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1136 _exptl_absorpt_coefficient_mu 4.758 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.86 _exptl_absorpt_correction_T_max 0.99 _exptl_absorpt_process_details 'Jacobson, R (1998) Private communication' _exptl_special_details ; ? ; _diffrn_ambient_temperature 455(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 ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7189 _diffrn_reflns_av_R_equivalents 0.0293 _diffrn_reflns_av_sigmaI/netI 0.0287 _diffrn_reflns_limit_h_min -24 _diffrn_reflns_limit_h_max 28 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 3.11 _diffrn_reflns_theta_max 31.12 _reflns_number_total 2318 _reflns_number_gt 1785 _reflns_threshold_expression >2sigma(I) _computing_data_collection CRYSTALCLEAR _computing_cell_refinement CRYSTALCLEAR _computing_data_reduction 'teXsan Ver. 1.11' _computing_structure_solution 'SIR-92 (Altomare et al. 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Mercury 1.4.1' _computing_publication_material 'PLATON (Spek, 2003)' _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^)+(0.0552P)^2^+6.2027P] 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 noref _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2318 _refine_ls_number_parameters 128 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0942 _refine_ls_R_factor_gt 0.0764 _refine_ls_wR_factor_ref 0.1834 _refine_ls_wR_factor_gt 0.1746 _refine_ls_goodness_of_fit_ref 1.578 _refine_ls_restrained_S_all 1.578 _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 0.20681(4) 0.68003(5) 0.28648(11) 0.0342(2) Uani 1 1 d . . . Cu2 Cu 0.0000 0.63303(14) -0.2500 0.0608(4) Uani 1 2 d S . . Cu3 Cu 0.0000 0.30041(15) -0.2500 0.0689(5) Uani 1 2 d S . . O1 O 0.1100(2) 0.6160(3) 0.0788(6) 0.0370(10) Uani 1 1 d . . . O2 O 0.0709(3) 0.4567(3) -0.0397(7) 0.0469(13) Uani 1 1 d . . . O3 O 0.1507(2) 0.2406(3) -0.0626(6) 0.0344(9) Uani 1 1 d . . . O4 O 0.0915(3) 0.2403(4) 0.1427(8) 0.0484(12) Uani 1 1 d . . . N1 N 0.2304(2) 0.5282(3) 0.3105(6) 0.0248(9) Uani 1 1 d . . . N2 N 0.2576(2) 0.3116(4) 0.3004(6) 0.0275(9) Uani 1 1 d . . . C1 C 0.2909(3) 0.4844(4) 0.4261(8) 0.0330(12) Uani 1 1 d . . . H1 H 0.3237 0.5267 0.5117 0.040 Uiso 1 1 calc R . . C2 C 0.3038(3) 0.3751(5) 0.4159(9) 0.0378(14) Uani 1 1 d . . . H2 H 0.3463 0.3462 0.4931 0.045 Uiso 1 1 calc R . . C3 C 0.1943(3) 0.3518(4) 0.1941(7) 0.0230(9) Uani 1 1 d . . . C4 C 0.1819(2) 0.4630(4) 0.1986(7) 0.0201(9) Uani 1 1 d . . . C5 C 0.1155(3) 0.5158(4) 0.0681(7) 0.0238(9) Uani 1 1 d . . . C6 C 0.1410(3) 0.2721(4) 0.0820(7) 0.0258(10) 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 0.0308(4) 0.0178(4) 0.0485(5) -0.0020(3) 0.0038(3) -0.0055(2) Cu2 0.0474(8) 0.0659(10) 0.0617(9) 0.000 0.0057(6) 0.000 Cu3 0.0596(9) 0.0613(10) 0.0703(10) 0.000 -0.0030(7) 0.000 O1 0.035(2) 0.0174(18) 0.046(2) 0.0022(16) -0.0068(17) 0.0013(14) O2 0.035(2) 0.028(2) 0.056(3) -0.0131(19) -0.018(2) 0.0047(17) O3 0.039(2) 0.028(2) 0.036(2) -0.0084(16) 0.0114(17) -0.0053(16) O4 0.041(2) 0.049(3) 0.064(3) -0.013(2) 0.030(2) -0.016(2) N1 0.0219(18) 0.022(2) 0.026(2) -0.0003(15) 0.0008(15) 0.0016(15) N2 0.0253(19) 0.021(2) 0.031(2) 0.0023(16) 0.0017(16) 0.0043(16) C1 0.026(2) 0.024(3) 0.037(3) -0.005(2) -0.008(2) 0.0029(19) C2 0.027(3) 0.027(3) 0.045(3) -0.003(2) -0.009(2) 0.011(2) C3 0.024(2) 0.018(2) 0.027(2) -0.0027(17) 0.0064(17) 0.0026(16) C4 0.0190(19) 0.013(2) 0.027(2) 0.0000(16) 0.0045(16) 0.0021(15) C5 0.024(2) 0.016(2) 0.026(2) -0.0020(17) 0.0005(17) 0.0011(16) C6 0.022(2) 0.021(2) 0.033(2) -0.0016(19) 0.0058(18) -0.0010(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 N1 1.950(4) . ? Cu1 N2 1.981(5) 4 ? Cu1 O3 2.074(4) 6_566 ? Cu1 O1 2.211(4) . ? O1 C5 1.264(6) . ? O2 C5 1.244(6) . ? O3 C6 1.250(7) . ? O3 Cu1 2.074(4) 6_565 ? O4 C6 1.255(7) . ? N1 C4 1.341(6) . ? N1 C1 1.353(7) . ? N2 C2 1.318(8) . ? N2 C3 1.348(6) . ? N2 Cu1 1.981(5) 4_545 ? C1 C2 1.397(8) . ? C1 H1 0.9300 . ? C2 H2 0.9300 . ? C3 C4 1.415(7) . ? C3 C6 1.505(7) . ? C4 C5 1.521(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 N1 Cu1 N2 138.33(19) . 4 ? N1 Cu1 O3 124.16(18) . 6_566 ? N2 Cu1 O3 95.06(18) 4 6_566 ? N1 Cu1 O1 80.66(16) . . ? N2 Cu1 O1 111.27(18) 4 . ? O3 Cu1 O1 96.07(19) 6_566 . ? C5 O1 Cu1 109.7(3) . . ? C6 O3 Cu1 126.7(4) . 6_565 ? C4 N1 C1 118.2(4) . . ? C4 N1 Cu1 115.8(3) . . ? C1 N1 Cu1 126.1(4) . . ? C2 N2 C3 119.3(5) . . ? C2 N2 Cu1 119.7(4) . 4_545 ? C3 N2 Cu1 116.8(4) . 4_545 ? N1 C1 C2 119.6(5) . . ? N1 C1 H1 120.2 . . ? C2 C1 H1 120.2 . . ? N2 C2 C1 122.2(5) . . ? N2 C2 H2 118.9 . . ? C1 C2 H2 118.9 . . ? N2 C3 C4 118.8(4) . . ? N2 C3 C6 116.0(4) . . ? C4 C3 C6 125.1(4) . . ? N1 C4 C3 121.7(4) . . ? N1 C4 C5 116.4(4) . . ? C3 C4 C5 121.8(4) . . ? O2 C5 O1 125.4(5) . . ? O2 C5 C4 117.3(4) . . ? O1 C5 C4 117.3(4) . . ? O4 C6 O3 125.0(5) . . ? O4 C6 C3 117.7(5) . . ? O3 C6 C3 117.3(5) . . ? 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 N1 Cu1 O1 C5 -2.0(4) . . . . ? N2 Cu1 O1 C5 136.5(4) 4 . . . ? O3 Cu1 O1 C5 -125.7(4) 6_566 . . . ? N2 Cu1 N1 C4 -110.7(4) 4 . . . ? O3 Cu1 N1 C4 91.9(4) 6_566 . . . ? O1 Cu1 N1 C4 0.9(4) . . . . ? N2 Cu1 N1 C1 68.0(6) 4 . . . ? O3 Cu1 N1 C1 -89.3(5) 6_566 . . . ? O1 Cu1 N1 C1 179.6(5) . . . . ? C4 N1 C1 C2 4.9(9) . . . . ? Cu1 N1 C1 C2 -173.8(5) . . . . ? C3 N2 C2 C1 -3.1(10) . . . . ? Cu1 N2 C2 C1 153.2(6) 4_545 . . . ? N1 C1 C2 N2 -2.2(11) . . . . ? C2 N2 C3 C4 5.3(8) . . . . ? Cu1 N2 C3 C4 -151.7(4) 4_545 . . . ? C2 N2 C3 C6 -173.2(6) . . . . ? Cu1 N2 C3 C6 29.8(6) 4_545 . . . ? C1 N1 C4 C3 -2.6(8) . . . . ? Cu1 N1 C4 C3 176.2(4) . . . . ? C1 N1 C4 C5 -178.7(5) . . . . ? Cu1 N1 C4 C5 0.2(6) . . . . ? N2 C3 C4 N1 -2.5(8) . . . . ? C6 C3 C4 N1 175.8(5) . . . . ? N2 C3 C4 C5 173.3(5) . . . . ? C6 C3 C4 C5 -8.3(8) . . . . ? Cu1 O1 C5 O2 -177.9(5) . . . . ? Cu1 O1 C5 C4 2.6(6) . . . . ? N1 C4 C5 O2 178.4(5) . . . . ? C3 C4 C5 O2 2.3(8) . . . . ? N1 C4 C5 O1 -2.1(7) . . . . ? C3 C4 C5 O1 -178.1(5) . . . . ? Cu1 O3 C6 O4 158.5(5) 6_565 . . . ? Cu1 O3 C6 C3 -23.3(7) 6_565 . . . ? N2 C3 C6 O4 97.9(6) . . . . ? C4 C3 C6 O4 -80.5(7) . . . . ? N2 C3 C6 O3 -80.4(6) . . . . ? C4 C3 C6 O3 101.2(6) . . . . ? _diffrn_measured_fraction_theta_max 0.803 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.867 _refine_diff_density_max 0.950 _refine_diff_density_min -1.327 _refine_diff_density_rms 0.202 data_compound1 _database_code_depnum_ccdc_archive 'CCDC 859370' #TrackingRef '- mcif.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C6 H2 Cu2 N2 O4.83' _chemical_formula_weight 307.18 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' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 19.4082(4) _cell_length_b 12.5929(2) _cell_length_c 7.5885(2) _cell_angle_alpha 90.00 _cell_angle_beta 107.0340(10) _cell_angle_gamma 90.00 _cell_volume 1773.31(7) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description Block _exptl_crystal_colour red _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_min 0.09 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.301 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1192 _exptl_absorpt_coefficient_mu 4.795 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.7364 _exptl_absorpt_correction_T_max 0.9891 _exptl_absorpt_process_details SADABS _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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7091 _diffrn_reflns_av_R_equivalents 0.0286 _diffrn_reflns_av_sigmaI/netI 0.0465 _diffrn_reflns_limit_h_min -24 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 1.95 _diffrn_reflns_theta_max 26.34 _reflns_number_total 1790 _reflns_number_gt 1517 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker,2000)' _computing_cell_refinement SMART _computing_data_reduction 'SAINT (Bruker,2000)' _computing_structure_solution 'SIR-92 (Altomare et al. 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Mercury 1.4.1' _computing_publication_material 'PLATON (Spek, 2003)' _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^)+(0.0516P)^2^+58.2626P] 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 noref _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1790 _refine_ls_number_parameters 136 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0813 _refine_ls_R_factor_gt 0.0695 _refine_ls_wR_factor_ref 0.1714 _refine_ls_wR_factor_gt 0.1625 _refine_ls_goodness_of_fit_ref 1.086 _refine_ls_restrained_S_all 1.086 _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 0.20534(5) 0.68383(6) 0.27775(13) 0.0210(3) Uani 1 1 d . . . Cu2 Cu 0.0000 0.62947(18) -0.2500 0.0586(6) Uani 1 2 d S . . Cu3 Cu 0.0000 0.30257(18) -0.2500 0.0630(6) Uani 1 2 d S . . O1 O 0.1092(3) 0.6144(4) 0.0830(7) 0.0212(11) Uani 1 1 d . . . O2 O 0.0715(3) 0.4544(4) -0.0260(7) 0.0263(12) Uani 1 1 d . . . O3 O 0.1498(3) 0.2441(4) -0.0552(7) 0.0208(11) Uani 1 1 d . . . O4 O 0.1002(3) 0.2410(5) 0.1733(9) 0.0334(14) Uani 1 1 d . . . N1 N 0.2319(3) 0.5337(4) 0.3087(8) 0.0151(12) Uani 1 1 d . . . N2 N 0.2619(3) 0.3180(4) 0.2998(8) 0.0183(12) Uani 1 1 d . . . C1 C 0.2941(4) 0.4923(5) 0.4169(10) 0.0201(15) Uani 1 1 d . . . H1 H 0.3272 0.5365 0.4971 0.024 Uiso 1 1 calc R . . C2 C 0.3093(4) 0.3857(6) 0.4106(10) 0.0235(16) Uani 1 1 d . . . H2 H 0.3532 0.3598 0.4843 0.028 Uiso 1 1 calc R . . C3 C 0.1976(4) 0.3580(5) 0.2002(9) 0.0144(13) Uani 1 1 d . . . C4 C 0.1835(3) 0.4669(5) 0.2013(8) 0.0116(12) Uani 1 1 d . . . C5 C 0.1157(4) 0.5160(5) 0.0753(9) 0.0161(14) Uani 1 1 d . . . C6 C 0.1441(3) 0.2749(5) 0.0943(9) 0.0149(13) Uani 1 1 d . . . O1W O 0.0019(11) 0.1016(17) -0.049(3) 0.148(11) Uiso 0.83(4) 1 d P . . 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 0.0206(5) 0.0070(4) 0.0321(5) -0.0009(3) 0.0026(4) -0.0028(3) Cu2 0.0524(12) 0.0656(14) 0.0542(12) 0.000 0.0100(9) 0.000 Cu3 0.0621(14) 0.0571(13) 0.0606(13) 0.000 0.0039(10) 0.000 O1 0.019(3) 0.010(2) 0.026(3) 0.0015(19) -0.006(2) 0.0034(19) O2 0.021(3) 0.014(2) 0.032(3) -0.010(2) -0.011(2) 0.001(2) O3 0.023(3) 0.014(2) 0.023(2) -0.0037(19) 0.004(2) -0.005(2) O4 0.037(3) 0.025(3) 0.047(3) -0.008(3) 0.025(3) -0.014(3) N1 0.014(3) 0.012(3) 0.018(3) 0.000(2) 0.003(2) -0.001(2) N2 0.022(3) 0.012(3) 0.017(3) 0.000(2) 0.000(2) 0.001(2) C1 0.018(4) 0.014(3) 0.022(3) -0.003(3) -0.004(3) 0.000(3) C2 0.016(4) 0.021(4) 0.025(4) 0.000(3) -0.007(3) 0.007(3) C3 0.019(4) 0.005(3) 0.020(3) 0.000(2) 0.007(3) 0.000(2) C4 0.011(3) 0.014(3) 0.012(3) 0.000(2) 0.006(2) 0.001(2) C5 0.018(3) 0.016(3) 0.018(3) 0.001(3) 0.010(3) 0.003(3) C6 0.011(3) 0.008(3) 0.026(3) -0.004(3) 0.006(3) 0.001(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 N2 1.955(6) 4 ? Cu1 N1 1.956(6) . ? Cu1 O3 2.096(5) 6_566 ? Cu1 O1 2.194(5) . ? O1 C5 1.249(8) . ? O2 C5 1.241(9) . ? O3 C6 1.234(8) . ? O3 Cu1 2.096(5) 6_565 ? O4 C6 1.251(9) . ? N1 C4 1.345(8) . ? N1 C1 1.349(9) . ? N2 C2 1.352(9) . ? N2 C3 1.354(9) . ? N2 Cu1 1.955(6) 4_545 ? C1 C2 1.378(10) . ? C1 H1 0.9300 . ? C2 H2 0.9300 . ? C3 C4 1.398(9) . ? C3 C6 1.527(9) . ? C4 C5 1.513(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 N2 Cu1 N1 140.7(3) 4 . ? N2 Cu1 O3 94.5(2) 4 6_566 ? N1 Cu1 O3 120.7(2) . 6_566 ? N2 Cu1 O1 115.4(2) 4 . ? N1 Cu1 O1 80.7(2) . . ? O3 Cu1 O1 95.4(2) 6_566 . ? C5 O1 Cu1 110.5(4) . . ? C6 O3 Cu1 128.3(4) . 6_565 ? C4 N1 C1 118.0(6) . . ? C4 N1 Cu1 114.8(4) . . ? C1 N1 Cu1 127.2(5) . . ? C2 N2 C3 117.4(6) . . ? C2 N2 Cu1 120.7(5) . 4_545 ? C3 N2 Cu1 118.8(4) . 4_545 ? N1 C1 C2 121.2(6) . . ? N1 C1 H1 119.4 . . ? C2 C1 H1 119.4 . . ? N2 C2 C1 121.5(6) . . ? N2 C2 H2 119.2 . . ? C1 C2 H2 119.2 . . ? N2 C3 C4 120.8(6) . . ? N2 C3 C6 114.3(5) . . ? C4 C3 C6 124.9(6) . . ? N1 C4 C3 120.9(6) . . ? N1 C4 C5 116.8(6) . . ? C3 C4 C5 122.2(6) . . ? O2 C5 O1 126.0(6) . . ? O2 C5 C4 116.8(6) . . ? O1 C5 C4 117.2(6) . . ? O3 C6 O4 126.2(6) . . ? O3 C6 C3 118.0(6) . . ? O4 C6 C3 115.7(6) . . ? _diffrn_measured_fraction_theta_max 0.985 _diffrn_reflns_theta_full 26.34 _diffrn_measured_fraction_theta_full 0.985 _refine_diff_density_max 1.131 _refine_diff_density_min -1.483 _refine_diff_density_rms 0.200