# Electronic Supplementary Material (ESI) for Dalton Transactions # 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_DG1 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H13 Cu N2 O5' _chemical_formula_weight 328.78 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 C2/c loop_ _space_group_symop_operation_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 28.642(2) _cell_length_b 13.1862(11) _cell_length_c 8.5395(6) _cell_angle_alpha 90 _cell_angle_beta 91.660(5) _cell_angle_gamma 90 _cell_volume 3223.8(4) _cell_formula_units_Z 8 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 250 _cell_measurement_theta_min 2.6 _cell_measurement_theta_max 26.5 _exptl_crystal_description Block _exptl_crystal_colour Green _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.355 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1344 _exptl_absorpt_coefficient_mu 1.372 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8567 _exptl_absorpt_correction_T_max 0.9683 _exptl_absorpt_process_details ; 'XPREP' - A PROGRAM DATA PREPARATION & RECIPROCAL SPACE EXPLORATION, Bruker Analytical X-ray Systems, 1997 ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_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 13405 _diffrn_reflns_av_R_equivalents 0.0417 _diffrn_reflns_av_unetI/netI 0.0391 _diffrn_reflns_limit_h_min -35 _diffrn_reflns_limit_h_max 35 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 2.63 _diffrn_reflns_theta_max 26.48 _reflns_number_total 3321 _reflns_number_gt 2818 _reflns_threshold_expression >2\s(I) _computing_data_collection 'SMART APEX II (Bruker,2010)' _computing_cell_refinement 'SMART APEX II' _computing_data_reduction 'SAINT (Bruker,2000)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Ortep-3v2 for windows (Farrugia, 1997)' _computing_publication_material 'PLATON (Spek, 2008)' _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^ > 2\s(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 'w=1/[\s^2^(Fo^2^)+(0.0844P)^2^+12.6846P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary ? _atom_sites_solution_secondary ? _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment noref _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3321 _refine_ls_number_parameters 184 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0599 _refine_ls_R_factor_gt 0.0515 _refine_ls_wR_factor_ref 0.1765 _refine_ls_wR_factor_gt 0.1713 _refine_ls_goodness_of_fit_ref 1.296 _refine_ls_restrained_S_all 1.296 _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_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.34606(16) -0.0262(4) 0.3393(6) 0.0241(10) Uani 1 1 d . . . . . H1 H 0.3233 0.0099 0.3914 0.029 Uiso 1 1 calc R U . . . C2 C 0.38013(16) 0.0272(4) 0.2630(6) 0.0256(10) Uani 1 1 d . . . . . H2 H 0.3800 0.0977 0.2639 0.031 Uiso 1 1 calc R U . . . C3 C 0.41442(15) -0.0247(4) 0.1852(5) 0.0216(9) Uani 1 1 d . . . . . C4 C 0.41183(18) -0.1292(4) 0.1841(6) 0.0307(11) Uani 1 1 d . . . . . H4 H 0.4339 -0.1672 0.1318 0.037 Uiso 1 1 calc R U . . . C5 C 0.37645(18) -0.1769(4) 0.2610(6) 0.0288(11) Uani 1 1 d . . . . . H5 H 0.3748 -0.2473 0.2569 0.035 Uiso 1 1 calc R U . . . C6 C 0.45244(15) 0.0304(4) 0.1032(5) 0.0235(10) Uani 1 1 d . . . . . C7 C 0.45207(18) 0.1425(4) 0.1080(7) 0.0375(13) Uani 1 1 d . . . . . H8A H 0.4781 0.1682 0.0518 0.056 Uiso 1 1 calc R U . . . H8B H 0.4544 0.1649 0.2149 0.056 Uiso 1 1 calc R U . . . H8C H 0.4235 0.1671 0.0605 0.056 Uiso 1 1 calc R U . . . C8 C 0.21016(15) -0.2346(3) 0.2318(5) 0.0149(8) Uani 1 1 d . . . . . C9 C 0.18721(16) -0.2111(3) 0.0744(5) 0.0174(9) Uani 1 1 d . . . . . H12A H 0.1536 -0.2089 0.0853 0.021 Uiso 1 1 calc R U . . . H12B H 0.1942 -0.2651 0.0015 0.021 Uiso 1 1 calc R U . . . C10 C 0.20374(16) -0.1099(3) 0.0076(5) 0.0183(9) Uani 1 1 d . . . . . H13A H 0.2369 -0.1140 -0.0118 0.022 Uiso 1 1 calc R U . . . H13B H 0.1875 -0.0973 -0.0917 0.022 Uiso 1 1 calc R U . . . C11 C 0.19484(16) -0.0217(3) 0.1196(5) 0.0196(9) Uani 1 1 d . . . . . H14A H 0.1614 -0.0150 0.1312 0.024 Uiso 1 1 calc R U . . . H14B H 0.2084 -0.0386 0.2216 0.024 Uiso 1 1 calc R U . . . C12 C 0.21414(14) 0.0803(3) 0.0696(5) 0.0159(8) Uani 1 1 d . . . . . N1 N 0.34433(12) -0.1269(3) 0.3416(4) 0.0172(7) Uani 1 1 d . . . . . N2 N 0.48203(14) -0.0265(3) 0.0369(5) 0.0290(9) Uani 1 1 d . . . . . O1 O 0.18559(11) -0.2781(3) 0.3329(4) 0.0239(7) Uani 1 1 d . . . . . O2 O 0.18905(10) 0.1562(2) 0.0902(4) 0.0213(7) Uani 1 1 d . . . . . O3 O 0.25200(11) -0.2084(2) 0.2527(4) 0.0201(7) Uani 1 1 d . . . . . O4 O 0.25419(11) 0.0812(2) 0.0139(4) 0.0222(7) Uani 1 1 d . . . . . Cu1 Cu 0.28809(2) -0.20535(4) 0.45252(5) 0.0131(2) Uani 1 1 d . . . . . O1W O 0.0931(6) 0.1037(12) -0.0620(17) 0.105(4) Uiso 0.5 1 d . . P . . O2W O 0.4388(12) -0.388(3) 0.041(4) 0.115(10) Uiso 0.25 1 d . . P . . O3W O 0.0366(13) 0.120(3) -0.262(4) 0.135(12) Uiso 0.25 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 C1 0.019(2) 0.021(2) 0.033(2) 0.0040(19) 0.0081(18) -0.0018(18) C2 0.022(2) 0.018(2) 0.036(3) 0.008(2) 0.0064(19) -0.0039(18) C3 0.019(2) 0.028(3) 0.018(2) 0.0069(18) -0.0004(16) -0.0086(18) C4 0.032(3) 0.026(3) 0.035(3) -0.002(2) 0.020(2) -0.005(2) C5 0.032(3) 0.022(2) 0.033(3) 0.000(2) 0.016(2) -0.007(2) C6 0.018(2) 0.033(3) 0.019(2) 0.0085(19) -0.0008(17) -0.0108(19) C7 0.028(3) 0.039(3) 0.047(3) 0.011(3) 0.010(2) -0.014(2) C8 0.021(2) 0.0097(19) 0.0138(19) -0.0021(15) 0.0033(16) 0.0010(16) C9 0.022(2) 0.014(2) 0.016(2) -0.0005(16) -0.0002(16) -0.0022(16) C10 0.027(2) 0.014(2) 0.0143(19) 0.0005(16) 0.0032(16) 0.0003(17) C11 0.028(2) 0.014(2) 0.018(2) 0.0002(17) 0.0088(17) 0.0002(17) C12 0.023(2) 0.014(2) 0.0110(19) -0.0012(15) 0.0015(16) 0.0006(16) N1 0.0162(16) 0.0190(19) 0.0166(16) 0.0021(14) 0.0028(13) -0.0044(14) N2 0.024(2) 0.037(3) 0.027(2) 0.0092(18) 0.0100(17) -0.0123(19) O1 0.0239(16) 0.0325(19) 0.0153(15) 0.0054(13) 0.0008(13) -0.0115(14) O2 0.0190(15) 0.0125(15) 0.0328(17) -0.0013(13) 0.0067(13) 0.0007(12) O3 0.0185(15) 0.0271(18) 0.0148(14) 0.0033(12) 0.0029(11) -0.0042(12) O4 0.0267(16) 0.0139(16) 0.0267(16) 0.0020(13) 0.0147(13) 0.0023(13) Cu1 0.0153(3) 0.0114(3) 0.0128(3) 0.00142(18) 0.00379(19) -0.00231(18) _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 C1 N1 1.329(6) . ? C1 C2 1.382(6) . ? C2 C3 1.382(7) . ? C3 C4 1.381(7) . ? C3 C6 1.499(6) . ? C4 C5 1.376(6) . ? C5 N1 1.339(6) . ? C6 N2 1.277(7) . ? C6 C7 1.479(8) . ? C8 O3 1.255(5) . ? C8 O1 1.266(5) . ? C8 C9 1.511(6) . ? C9 C10 1.531(6) . ? C10 C11 1.532(6) . ? C11 C12 1.520(6) . ? C12 O4 1.254(5) . ? C12 O2 1.248(5) . ? N1 Cu1 2.157(3) . ? N2 N2 1.408(7) 5_655 ? O1 Cu1 1.973(3) 7_546 ? O2 Cu1 1.977(3) 4 ? O3 Cu1 1.969(3) . ? O4 Cu1 1.981(3) 6 ? Cu1 O1 1.973(3) 7_546 ? Cu1 O2 1.977(3) 4_545 ? Cu1 O4 1.981(3) 6_556 ? Cu1 Cu1 2.6280(9) 7_546 ? 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 C1 C2 122.9(4) . . ? C3 C2 C1 119.7(4) . . ? C2 C3 C4 117.3(4) . . ? C2 C3 C6 121.4(4) . . ? C4 C3 C6 121.3(4) . . ? C5 C4 C3 119.6(5) . . ? N1 C5 C4 123.1(5) . . ? N2 C6 C7 127.3(4) . . ? N2 C6 C3 115.0(4) . . ? C7 C6 C3 117.7(4) . . ? O3 C8 O1 125.1(4) . . ? O3 C8 C9 117.3(4) . . ? O1 C8 C9 117.6(4) . . ? C8 C9 C10 112.3(3) . . ? C11 C10 C9 111.7(3) . . ? C12 C11 C10 115.4(3) . . ? O4 C12 O2 125.6(4) . . ? O4 C12 C11 117.3(4) . . ? O2 C12 C11 117.0(4) . . ? C1 N1 C5 117.3(4) . . ? C1 N1 Cu1 121.0(3) . . ? C5 N1 Cu1 121.5(3) . . ? C6 N2 N2 114.2(5) . 5_655 ? C8 O1 Cu1 118.6(3) . 7_546 ? C12 O2 Cu1 121.3(3) . 4 ? C8 O3 Cu1 127.1(3) . . ? C12 O4 Cu1 124.7(3) . 6 ? O3 Cu1 O1 168.25(13) . 7_546 ? O3 Cu1 O2 89.41(13) . 4_545 ? O1 Cu1 O2 87.10(14) 7_546 4_545 ? O3 Cu1 O4 89.84(14) . 6_556 ? O1 Cu1 O4 91.30(14) 7_546 6_556 ? O2 Cu1 O4 168.26(13) 4_545 6_556 ? O3 Cu1 N1 90.53(13) . . ? O1 Cu1 N1 101.00(13) 7_546 . ? O2 Cu1 N1 96.11(13) 4_545 . ? O4 Cu1 N1 95.62(13) 6_556 . ? O3 Cu1 Cu1 80.72(9) . 7_546 ? O1 Cu1 Cu1 87.83(9) 7_546 7_546 ? O2 Cu1 Cu1 85.73(9) 4_545 7_546 ? O4 Cu1 Cu1 82.58(9) 6_556 7_546 ? N1 Cu1 Cu1 171.05(10) . 7_546 ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 26.48 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 1.548 _refine_diff_density_min -0.444 _refine_diff_density_rms 0.148 _database_code_depnum_ccdc_archive 'CCDC 944115' ####################################################################### # # 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_DG2 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H13 Cu N2 O4' _chemical_formula_weight 312.78 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 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 29.2971(11) _cell_length_b 13.1552(4) _cell_length_c 8.5923(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.723(4) _cell_angle_gamma 90.00 _cell_volume 3311.3(2) _cell_formula_units_Z 8 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 250 _cell_measurement_theta_min 1.4 _cell_measurement_theta_max 27.7 _exptl_crystal_description Block _exptl_crystal_colour Green _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.255 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1280 _exptl_absorpt_coefficient_mu 1.328 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8967 _exptl_absorpt_correction_T_max 0.9682 _exptl_absorpt_process_details ; 'XPREP' - A PROGRAM DATA PREPARATION & RECIPROCAL SPACE EXPLORATION, Bruker Analytical X-ray Systems, 1997 ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(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 17362 _diffrn_reflns_av_R_equivalents 0.0606 _diffrn_reflns_av_unetI/netI 0.0634 _diffrn_reflns_limit_h_min -38 _diffrn_reflns_limit_h_max 38 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 1.70 _diffrn_reflns_theta_max 27.58 _reflns_number_total 3796 _reflns_number_gt 2504 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART APEX II (Bruker,2010)' _computing_cell_refinement 'SMART APEX II' _computing_data_reduction 'SAINT (Bruker,2000)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Ortep-3v2 for windows (Farrugia, 1997)' _computing_publication_material 'PLATON (Spek, 2008)' _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. Checkcif output: PLAT602_ALERT_2_A VERY LARGE Solvent Accessible VOID(S) in Structure ! The void is usual in such dehydrated framework structure showing single crystal to single crystal structural transformation. The said crystal was obtained by heating of as-synthesized single crystal DG1 at 110 degrees C under vacuum to remove the entire solvent (water here) molecule. ; _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^)+(0.0989P)^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 noref _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3796 _refine_ls_number_parameters 172 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0855 _refine_ls_R_factor_gt 0.0487 _refine_ls_wR_factor_ref 0.1732 _refine_ls_wR_factor_gt 0.1435 _refine_ls_goodness_of_fit_ref 1.036 _refine_ls_restrained_S_all 1.036 _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 0.213094(14) -0.20401(4) 0.44769(5) 0.02961(19) Uani 1 1 d . . . O3 O 0.24830(10) -0.2055(2) 0.2542(3) 0.0408(7) Uani 1 1 d . . . O1 O 0.31177(10) -0.2797(2) 0.3417(3) 0.0434(8) Uani 1 1 d . . . O4 O 0.30919(9) 0.1581(2) 0.0994(3) 0.0411(7) Uani 1 1 d . . . O2 O 0.24663(10) 0.0800(2) 0.0125(4) 0.0435(8) Uani 1 1 d . . . N1 N 0.15718(11) -0.1254(3) 0.3325(4) 0.0372(8) Uani 1 1 d . . . C3 C 0.08660(13) -0.0234(4) 0.1789(5) 0.0433(11) Uani 1 1 d . . . N2 N 0.01833(13) -0.0268(4) 0.0368(5) 0.0670(13) Uani 1 1 d . . . C9 C 0.31124(15) -0.2109(3) 0.0868(5) 0.0383(10) Uani 1 1 d . . . H9A H 0.3045 -0.2653 0.0138 0.046 Uiso 1 1 calc R . . H9B H 0.3441 -0.2089 0.1028 0.046 Uiso 1 1 calc R . . C11 C 0.30579(15) -0.0207(3) 0.1228(5) 0.0416(10) Uani 1 1 d . . . H11A H 0.3387 -0.0132 0.1315 0.050 Uiso 1 1 calc R . . H11B H 0.2946 -0.0369 0.2256 0.050 Uiso 1 1 calc R . . C8 C 0.28887(13) -0.2340(3) 0.2386(5) 0.0330(9) Uani 1 1 d . . . C12 C 0.28561(13) 0.0808(3) 0.0729(4) 0.0319(9) Uani 1 1 d . . . C4 C 0.12232(15) 0.0273(4) 0.2443(6) 0.0593(14) Uani 1 1 d . . . H4 H 0.1236 0.0979 0.2387 0.071 Uiso 1 1 calc R . . C5 C 0.15685(15) -0.0260(4) 0.3194(6) 0.0554(13) Uani 1 1 d . . . H5 H 0.1811 0.0105 0.3627 0.066 Uiso 1 1 calc R . . C10 C 0.29550(15) -0.1098(3) 0.0160(5) 0.0417(10) Uani 1 1 d . . . H10A H 0.3107 -0.0994 -0.0824 0.050 Uiso 1 1 calc R . . H10B H 0.2629 -0.1127 -0.0047 0.050 Uiso 1 1 calc R . . C6 C 0.04819(14) 0.0311(4) 0.1020(5) 0.0492(12) Uani 1 1 d . . . C2 C 0.08728(16) -0.1277(4) 0.1901(6) 0.0688(16) Uani 1 1 d . . . H2 H 0.0638 -0.1661 0.1462 0.083 Uiso 1 1 calc R . . C1 C 0.12292(17) -0.1749(4) 0.2666(7) 0.0654(16) Uani 1 1 d . . . H1 H 0.1229 -0.2455 0.2722 0.078 Uiso 1 1 calc R . . C7 C 0.04760(19) 0.1442(5) 0.1082(7) 0.0798(19) Uani 1 1 d . . . H7A H 0.0210 0.1691 0.0539 0.120 Uiso 1 1 calc R . . H7B H 0.0745 0.1704 0.0599 0.120 Uiso 1 1 calc R . . H7C H 0.0469 0.1660 0.2148 0.120 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 0.0318(3) 0.0253(3) 0.0314(3) 0.0023(2) -0.00993(19) 0.00418(19) O3 0.0378(15) 0.049(2) 0.0353(17) 0.0077(14) -0.0060(12) 0.0058(13) O1 0.0489(17) 0.049(2) 0.0320(16) 0.0076(14) -0.0016(13) 0.0171(14) O4 0.0442(16) 0.0278(16) 0.0508(19) -0.0020(14) -0.0146(14) 0.0001(14) O2 0.0451(16) 0.0273(16) 0.057(2) 0.0024(15) -0.0220(14) -0.0017(13) N1 0.0357(17) 0.034(2) 0.042(2) 0.0075(17) -0.0125(15) 0.0031(15) C3 0.034(2) 0.053(3) 0.044(3) 0.014(2) -0.0077(18) 0.012(2) N2 0.046(2) 0.067(3) 0.087(3) 0.022(3) -0.027(2) 0.015(2) C9 0.052(2) 0.030(2) 0.033(2) 0.0031(18) 0.0008(19) 0.0050(19) C11 0.054(3) 0.028(2) 0.042(3) 0.001(2) -0.021(2) 0.0019(19) C8 0.041(2) 0.024(2) 0.034(2) 0.0001(17) -0.0048(17) -0.0013(17) C12 0.038(2) 0.033(2) 0.025(2) -0.0040(17) -0.0042(16) 0.0002(18) C4 0.047(3) 0.039(3) 0.091(4) 0.021(3) -0.031(3) 0.000(2) C5 0.042(2) 0.043(3) 0.081(4) 0.013(3) -0.027(2) -0.002(2) C10 0.059(3) 0.031(2) 0.035(2) 0.0028(19) -0.003(2) 0.000(2) C6 0.036(2) 0.059(3) 0.052(3) 0.016(2) -0.007(2) 0.015(2) C2 0.053(3) 0.057(4) 0.096(4) 0.000(3) -0.046(3) 0.005(3) C1 0.057(3) 0.036(3) 0.102(5) 0.009(3) -0.047(3) 0.002(2) C7 0.070(4) 0.065(4) 0.104(5) 0.022(4) -0.034(3) 0.021(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 O3 1.967(3) . ? Cu1 O4 1.968(3) 4_545 ? Cu1 O1 1.971(3) 7_546 ? Cu1 O2 1.981(3) 6_556 ? Cu1 N1 2.166(3) . ? Cu1 Cu1 2.6268(8) 7_546 ? O3 C8 1.255(5) . ? O1 C8 1.258(5) . ? O1 Cu1 1.971(3) 7_546 ? O4 C12 1.248(5) . ? O4 Cu1 1.968(3) 4 ? O2 C12 1.249(4) . ? O2 Cu1 1.981(3) 6 ? N1 C5 1.313(6) . ? N1 C1 1.318(6) . ? C3 C4 1.357(6) . ? C3 C2 1.376(7) . ? C3 C6 1.483(5) . ? N2 C6 1.284(6) . ? N2 N2 1.426(7) 5 ? C9 C8 1.498(5) . ? C9 C10 1.532(6) . ? C11 C10 1.517(6) . ? C11 C12 1.520(6) . ? C4 C5 1.384(6) . ? C6 C7 1.488(8) . ? C2 C1 1.375(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 O3 Cu1 O4 89.59(12) . 4_545 ? O3 Cu1 O1 168.07(11) . 7_546 ? O4 Cu1 O1 87.88(13) 4_545 7_546 ? O3 Cu1 O2 88.99(13) . 6_556 ? O4 Cu1 O2 168.25(11) 4_545 6_556 ? O1 Cu1 O2 91.12(13) 7_546 6_556 ? O3 Cu1 N1 91.16(12) . . ? O4 Cu1 N1 95.67(12) 4_545 . ? O1 Cu1 N1 100.69(12) 7_546 . ? O2 Cu1 N1 96.02(12) 6_556 . ? O3 Cu1 Cu1 81.17(8) . 7_546 ? O4 Cu1 Cu1 85.15(8) 4_545 7_546 ? O1 Cu1 Cu1 87.00(9) 7_546 7_546 ? O2 Cu1 Cu1 83.11(8) 6_556 7_546 ? N1 Cu1 Cu1 172.28(9) . 7_546 ? C8 O3 Cu1 126.9(3) . . ? C8 O1 Cu1 119.9(3) . 7_546 ? C12 O4 Cu1 122.1(3) . 4 ? C12 O2 Cu1 123.9(3) . 6 ? C5 N1 C1 116.7(4) . . ? C5 N1 Cu1 121.3(3) . . ? C1 N1 Cu1 121.9(3) . . ? C4 C3 C2 116.8(4) . . ? C4 C3 C6 121.6(5) . . ? C2 C3 C6 121.6(4) . . ? C6 N2 N2 113.9(6) . 5 ? C8 C9 C10 112.9(3) . . ? C10 C11 C12 115.8(3) . . ? O3 C8 O1 124.4(4) . . ? O3 C8 C9 117.3(4) . . ? O1 C8 C9 118.3(4) . . ? O4 C12 O2 125.8(4) . . ? O4 C12 C11 116.8(3) . . ? O2 C12 C11 117.4(4) . . ? C3 C4 C5 119.9(5) . . ? N1 C5 C4 123.3(4) . . ? C11 C10 C9 112.0(3) . . ? N2 C6 C3 114.6(4) . . ? N2 C6 C7 126.9(4) . . ? C3 C6 C7 118.5(4) . . ? C1 C2 C3 119.6(5) . . ? N1 C1 C2 123.5(5) . . ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 27.58 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.563 _refine_diff_density_min -0.549 _refine_diff_density_rms 0.137 _vrf_PLAT602_DG3 ; PROBLEM: VERY LARGE Solvent Accessible VOID(S) in Structure ! RESPONSE:... The void is usual in such dehydrated framework structure showing Single- Crystal-to-Single-Crystal Structural Transformation. The said crystal was obtained by heating of as-synthesized single crystal DG1 at 110 degrees C under vacuum to remove the entire solvent (water here) molecule. ; # end Validation Reply Form _database_code_depnum_ccdc_archive 'CCDC 944116' ####################################################################### # # 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_DG3 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H13 Cu N2 O5' _chemical_formula_weight 328.78 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' _space_group_crystal_system Monoclinic _space_group_name_H-M_alt C2/c loop_ _space_group_symop_operation_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 29.135(5) _cell_length_b 13.191(5) _cell_length_c 8.599(5) _cell_angle_alpha 90.000(5) _cell_angle_beta 90.247(5) _cell_angle_gamma 90.000(5) _cell_volume 3305(2) _cell_formula_units_Z 8 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 250 _cell_measurement_theta_min 1.4 _cell_measurement_theta_max 27.7 _exptl_crystal_description Block _exptl_crystal_colour Green _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.322 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1344 _exptl_absorpt_coefficient_mu 1.338 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8967 _exptl_absorpt_correction_T_max 0.9682 _exptl_absorpt_process_details ; 'XPREP' - A PROGRAM DATA PREPARATION & RECIPROCAL SPACE EXPLORATION, Bruker Analytical X-ray Systems, 1997 ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(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 26731 _diffrn_reflns_av_R_equivalents 0.0687 _diffrn_reflns_av_unetI/netI 0.0540 _diffrn_reflns_limit_h_min -36 _diffrn_reflns_limit_h_max 37 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 1.40 _diffrn_reflns_theta_max 27.66 _reflns_number_total 3818 _reflns_number_gt 2644 _reflns_threshold_expression >2\s(I) _computing_data_collection 'SMART APEX II (Bruker,2010)' _computing_cell_refinement 'SMART APEX II' _computing_data_reduction 'SAINT (Bruker,2000)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Ortep-3v2 for windows (Farrugia, 1997)' _computing_publication_material 'PLATON (Spek, 2008)' _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^ > 2\s(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^)+(0.1062P)^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 noref _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3818 _refine_ls_number_parameters 181 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0880 _refine_ls_R_factor_gt 0.0546 _refine_ls_wR_factor_ref 0.1793 _refine_ls_wR_factor_gt 0.1551 _refine_ls_goodness_of_fit_ref 1.078 _refine_ls_restrained_S_all 1.078 _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_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.37646(18) -0.1746(3) 0.7388(6) 0.0620(14) Uani 1 1 d . . . . . H1 H 0.3761 -0.2451 0.7373 0.074 Uiso 1 1 calc R U . . . C2 C 0.41149(17) -0.1275(4) 0.8167(6) 0.0712(16) Uani 1 1 d . . . . . H2 H 0.4338 -0.1660 0.8670 0.085 Uiso 1 1 calc R U . . . C3 C 0.41390(14) -0.0242(3) 0.8211(5) 0.0465(10) Uani 1 1 d . . . . . C4 C 0.37858(15) 0.0271(3) 0.7475(6) 0.0593(13) Uani 1 1 d . . . . . H4 H 0.3778 0.0975 0.7493 0.071 Uiso 1 1 calc R U . . . C5 C 0.34447(16) -0.0262(3) 0.6716(6) 0.0557(12) Uani 1 1 d . . . . . H5 H 0.3213 0.0102 0.6221 0.067 Uiso 1 1 calc R U . . . C6 C 0.45202(14) 0.0304(4) 0.9001(5) 0.0515(11) Uani 1 1 d . . . . . C7 C 0.45216(19) 0.1425(4) 0.8969(7) 0.0854(19) Uani 1 1 d . . . . . H7A H 0.4787 0.1673 0.9515 0.128 Uiso 1 1 calc R U . . . H7B H 0.4249 0.1676 0.9463 0.128 Uiso 1 1 calc R U . . . H7C H 0.4529 0.1655 0.7911 0.128 Uiso 1 1 calc R U . . . C8 C 0.21112(14) -0.2334(3) 0.7620(4) 0.0347(8) Uani 1 1 d . . . . . C9 C 0.18851(16) -0.2100(3) 0.9152(4) 0.0398(9) Uani 1 1 d . . . . . H9A H 0.1951 -0.2642 0.9882 0.048 Uiso 1 1 calc R U . . . H9B H 0.1555 -0.2071 0.9003 0.048 Uiso 1 1 calc R U . . . C10 C 0.20519(15) -0.1095(3) 0.9834(4) 0.0413(9) Uani 1 1 d . . . . . H10A H 0.1903 -0.0981 1.0825 0.050 Uiso 1 1 calc R U . . . H10B H 0.2380 -0.1135 1.0022 0.050 Uiso 1 1 calc R U . . . C11 C 0.19527(15) -0.0210(3) 0.8764(5) 0.0433(10) Uani 1 1 d . . . . . H11A H 0.1622 -0.0144 0.8655 0.052 Uiso 1 1 calc R U . . . H11B H 0.2075 -0.0367 0.7744 0.052 Uiso 1 1 calc R U . . . C12 C 0.21454(13) 0.0808(3) 0.9275(4) 0.0340(8) Uani 1 1 d . . . . . N1 N 0.34310(11) -0.1264(2) 0.6655(4) 0.0396(8) Uani 1 1 d . . . . . N2 N 0.48184(14) -0.0265(3) 0.9640(5) 0.0693(12) Uani 1 1 d . . . . . O3 O 0.25193(10) -0.2070(2) 0.7458(3) 0.0422(7) Uani 1 1 d . . . . . O1 O 0.18730(11) -0.2778(2) 0.6600(3) 0.0470(7) Uani 1 1 d . . . . . O2 O 0.19042(10) 0.1567(2) 0.9037(3) 0.0449(7) Uani 1 1 d . . . . . O4 O 0.25385(10) 0.08120(18) 0.9855(3) 0.0449(7) Uani 1 1 d . . . . . Cu1 Cu 0.28745(2) -0.20482(3) 0.55066(5) 0.0315(2) Uani 1 1 d . . . . . O1W O 0.4007(5) 0.3852(12) 0.9140(16) 0.165(5) Uiso 0.5 1 d . . P . . O2W O 0.442(2) 0.606(5) 0.901(6) 0.31(2) Uiso 0.25 1 d . . P . . O3W O 0.4567(14) -0.379(3) 1.183(5) 0.252(18) Uiso 0.25 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 C1 0.064(3) 0.038(2) 0.084(4) -0.001(2) -0.037(3) -0.010(2) C2 0.064(3) 0.052(3) 0.097(4) -0.001(3) -0.047(3) -0.009(2) C3 0.038(2) 0.051(2) 0.051(2) -0.011(2) -0.0043(19) -0.0095(19) C4 0.049(3) 0.037(2) 0.091(4) -0.015(2) -0.026(3) -0.002(2) C5 0.050(2) 0.039(2) 0.078(3) -0.009(2) -0.026(2) -0.004(2) C6 0.043(2) 0.062(3) 0.049(2) -0.016(2) -0.006(2) -0.014(2) C7 0.070(4) 0.070(4) 0.116(5) -0.028(3) -0.027(4) -0.025(3) C8 0.049(2) 0.0213(16) 0.0336(19) 0.0006(14) -0.0049(17) -0.0022(15) C9 0.056(3) 0.0293(19) 0.034(2) 0.0000(15) 0.0043(18) -0.0057(17) C10 0.063(3) 0.0295(19) 0.0310(19) -0.0026(15) -0.0060(19) -0.0011(17) C11 0.056(3) 0.0291(19) 0.045(2) -0.0034(16) -0.017(2) -0.0019(17) C12 0.040(2) 0.033(2) 0.0290(19) 0.0033(14) -0.0063(17) -0.0014(16) N1 0.0384(17) 0.0366(18) 0.0437(18) -0.0071(14) -0.0131(15) -0.0066(14) N2 0.055(2) 0.067(3) 0.085(3) -0.022(2) -0.028(2) -0.018(2) O3 0.0432(16) 0.0505(17) 0.0327(14) -0.0074(11) -0.0051(12) -0.0049(12) O1 0.0529(17) 0.0521(17) 0.0358(15) -0.0084(13) -0.0009(13) -0.0165(13) O2 0.0465(16) 0.0280(14) 0.0600(18) -0.0002(13) -0.0152(14) 0.0020(12) O4 0.0557(18) 0.0262(14) 0.0525(17) -0.0026(12) -0.0218(14) 0.0035(12) Cu1 0.0372(3) 0.0249(3) 0.0324(3) -0.00283(17) -0.00879(19) -0.00385(18) _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 C1 N1 1.319(6) . ? C1 C2 1.368(6) . ? C2 C3 1.364(7) . ? C3 C4 1.383(6) . ? C3 C6 1.486(5) . ? C4 C5 1.379(6) . ? C5 N1 1.324(5) . ? C6 N2 1.271(6) . ? C6 C7 1.480(8) . ? C8 O3 1.247(5) . ? C8 O1 1.260(5) . ? C8 C9 1.508(5) . ? C9 C10 1.528(5) . ? C10 C11 1.514(5) . ? C11 C12 1.519(5) . ? C12 O2 1.240(5) . ? C12 O4 1.247(4) . ? N1 Cu1 2.159(3) . ? N2 N2 1.410(7) 5_657 ? O3 Cu1 1.976(3) . ? O1 Cu1 1.972(3) 7_546 ? O2 Cu1 1.975(3) 4_556 ? O4 Cu1 1.981(3) 6_556 ? Cu1 O1 1.972(3) 7_546 ? Cu1 O2 1.975(3) 4_546 ? Cu1 O4 1.982(3) 6 ? Cu1 Cu1 2.6318(9) 7_546 ? 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 C1 C2 124.2(4) . . ? C3 C2 C1 120.3(5) . . ? C2 C3 C4 116.0(4) . . ? C2 C3 C6 122.3(4) . . ? C4 C3 C6 121.7(4) . . ? C5 C4 C3 120.1(4) . . ? N1 C5 C4 123.3(4) . . ? N2 C6 C7 126.6(4) . . ? N2 C6 C3 114.8(4) . . ? C7 C6 C3 118.6(4) . . ? O3 C8 O1 125.1(4) . . ? O3 C8 C9 117.4(3) . . ? O1 C8 C9 117.5(4) . . ? C8 C9 C10 111.9(3) . . ? C11 C10 C9 112.1(3) . . ? C10 C11 C12 115.9(3) . . ? O2 C12 O4 125.5(4) . . ? O2 C12 C11 117.2(3) . . ? O4 C12 C11 117.2(3) . . ? C1 N1 C5 116.1(3) . . ? C1 N1 Cu1 122.5(3) . . ? C5 N1 Cu1 121.3(3) . . ? C6 N2 N2 114.0(5) . 5_657 ? C8 O3 Cu1 127.0(3) . . ? C8 O1 Cu1 119.1(3) . 7_546 ? C12 O2 Cu1 122.0(3) . 4_556 ? C12 O4 Cu1 124.6(2) . 6_556 ? O1 Cu1 O2 87.25(13) 7_546 4_546 ? O1 Cu1 O3 167.87(11) 7_546 . ? O2 Cu1 O3 89.39(12) 4_546 . ? O1 Cu1 O4 91.25(13) 7_546 6 ? O2 Cu1 O4 167.77(11) 4_546 6 ? O3 Cu1 O4 89.56(12) . 6 ? O1 Cu1 N1 101.16(12) 7_546 . ? O2 Cu1 N1 96.23(12) 4_546 . ? O3 Cu1 N1 90.78(12) . . ? O4 Cu1 N1 95.97(11) 6 . ? O1 Cu1 Cu1 87.44(9) 7_546 7_546 ? O2 Cu1 Cu1 85.21(8) 4_546 7_546 ? O3 Cu1 Cu1 80.67(9) . 7_546 ? O4 Cu1 Cu1 82.60(8) 6 7_546 ? N1 Cu1 Cu1 171.33(9) . 7_546 ? _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 27.66 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 0.760 _refine_diff_density_min -0.687 _refine_diff_density_rms 0.268 _database_code_depnum_ccdc_archive 'CCDC 944117' ####################################################################### # # 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_DG4 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H11 N2 O5 Zn' _chemical_formula_weight 352.62 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' Zn Zn 0.2839 1.4301 '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_ _space_group_symop_operation_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 9.0842(2) _cell_length_b 14.7259(4) _cell_length_c 10.7959(3) _cell_angle_alpha 90 _cell_angle_beta 107.0830(10) _cell_angle_gamma 90 _cell_volume 1380.48(6) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 250 _cell_measurement_theta_min 2.4 _cell_measurement_theta_max 27.6 _exptl_crystal_description Block _exptl_crystal_colour Yellow _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.687 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 716 _exptl_absorpt_coefficient_mu 1.805 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8956 _exptl_absorpt_correction_T_max 0.9673 _exptl_absorpt_process_details ; 'XPREP' - A PROGRAM DATA PREPARATION & RECIPROCAL SPACE EXPLORATION, Bruker Analytical X-ray Systems, 1997 ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(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 22400 _diffrn_reflns_av_R_equivalents 0.0315 _diffrn_reflns_av_unetI/netI 0.0199 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.41 _diffrn_reflns_theta_max 27.65 _reflns_number_total 3209 _reflns_number_gt 2884 _reflns_threshold_expression >2\s(I) _computing_data_collection 'SMART APEX II (Bruker,2010)' _computing_cell_refinement 'SMART APEX II' _computing_data_reduction 'SAINT (Bruker,2000)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Ortep-3v2 for windows (Farrugia, 1997)' _computing_publication_material 'PLATON (Spek, 2008)' _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^ > 2\s(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^)+(0.0264P)^2^+2.1290P] 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 3209 _refine_ls_number_parameters 203 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0317 _refine_ls_R_factor_gt 0.0286 _refine_ls_wR_factor_ref 0.0738 _refine_ls_wR_factor_gt 0.0721 _refine_ls_goodness_of_fit_ref 1.083 _refine_ls_restrained_S_all 1.083 _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_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group O3 O 1.0505(2) 0.39260(13) -0.31942(16) 0.0271(4) Uani 1 1 d . . . . . O2 O 0.4753(2) 0.08731(15) -0.19180(16) 0.0308(5) Uani 1 1 d . . . . . O4 O 0.84115(19) 0.39496(13) -0.48941(18) 0.0281(4) Uani 1 1 d . . . . . N2 N 1.4274(2) 0.00952(14) 0.4562(2) 0.0180(4) Uani 1 1 d . . . . . O1W O 1.3209(3) 0.28274(19) -0.1693(3) 0.0557(7) Uani 1 1 d G . . . . H1WA H 1.3652 0.2338 -0.1797 0.084 Uiso 1 1 d G U . . . H1WB H 1.2352 0.2873 -0.2281 0.084 Uiso 1 1 d G U . . . H14 H 1.342(3) -0.0766(19) 0.554(3) 0.019(7) Uiso 1 1 d . . . . . Zn1 Zn 0.64356(2) -0.00088(2) 0.11179(2) 0.00792(9) Uani 1 1 d . . . . . C5 C 0.8409(2) 0.29787(14) -0.3174(2) 0.0116(4) Uani 1 1 d . . . . . C2 C 0.6887(2) 0.17629(14) -0.1989(2) 0.0123(4) Uani 1 1 d . . . . . O1 O 0.68520(18) 0.08410(13) -0.02230(17) 0.0248(4) Uani 1 1 d . . . . . C9 C 0.8985(2) -0.07542(15) 0.3301(2) 0.0149(4) Uani 1 1 d . . . . . H9 H 0.8224 -0.1148 0.3394 0.018 Uiso 1 1 calc R U . . . C4 C 0.6902(2) 0.27067(14) -0.3801(2) 0.0126(4) Uani 1 1 d . . . . . H4 H 0.6401 0.2933 -0.4621 0.015 Uiso 1 1 calc R U . . . C1 C 0.6100(2) 0.11077(14) -0.1324(2) 0.0130(4) Uani 1 1 d . . . . . C10 C 1.0466(2) -0.08550(15) 0.4124(2) 0.0154(4) Uani 1 1 d . . . . . H10 H 1.0689 -0.1304 0.4759 0.018 Uiso 1 1 calc R U . . . C3 C 0.6144(2) 0.21041(15) -0.3215(2) 0.0125(4) Uani 1 1 d . . . . . H3 H 0.5139 0.1928 -0.3641 0.015 Uiso 1 1 calc R U . . . C11 C 1.1612(2) -0.02736(16) 0.3985(2) 0.0145(4) Uani 1 1 d . . . . . N1 N 0.8598(2) -0.01147(12) 0.23756(18) 0.0129(4) Uani 1 1 d . . . . . C7 C 0.8398(3) 0.20285(17) -0.1370(2) 0.0184(5) Uani 1 1 d . . . . . H7 H 0.8904 0.1796 -0.0555 0.022 Uiso 1 1 calc R U . . . C8 C 0.9169(2) 0.36711(14) -0.3805(2) 0.0129(4) Uani 1 1 d . . . . . C6 C 0.9155(2) 0.26337(16) -0.1952(2) 0.0178(4) Uani 1 1 d . . . . . H6 H 1.0161 0.2809 -0.1527 0.021 Uiso 1 1 calc R U . . . C14 C 1.3210(2) -0.03613(16) 0.4830(2) 0.0161(4) Uani 1 1 d . . . . . C12 C 1.1211(3) 0.03944(19) 0.3037(2) 0.0248(5) Uani 1 1 d . . . . . H12 H 1.1949 0.0798 0.2925 0.030 Uiso 1 1 calc R U . . . C13 C 0.9706(3) 0.04526(18) 0.2263(2) 0.0235(5) Uani 1 1 d . . . . . H13 H 0.9449 0.0905 0.1635 0.028 Uiso 1 1 calc R U . . . 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 O3 0.0258(9) 0.0361(11) 0.0166(8) 0.0050(7) 0.0020(7) -0.0217(8) O2 0.0281(9) 0.0460(12) 0.0150(8) 0.0056(8) 0.0012(7) -0.0264(9) O4 0.0159(8) 0.0328(10) 0.0322(10) 0.0234(8) 0.0017(7) -0.0042(7) N2 0.0091(9) 0.0236(10) 0.0182(9) 0.0008(8) -0.0011(8) 0.0024(7) O1W 0.0508(15) 0.0473(16) 0.0628(17) -0.0005(13) 0.0068(13) 0.0040(12) Zn1 0.00672(13) 0.00822(14) 0.00862(13) 0.00005(8) 0.00194(9) -0.00020(8) C5 0.0122(9) 0.0099(9) 0.0133(9) 0.0007(7) 0.0049(7) -0.0009(7) C2 0.0139(9) 0.0109(10) 0.0131(9) 0.0006(8) 0.0055(8) -0.0023(8) O1 0.0145(7) 0.0345(10) 0.0262(9) 0.0195(8) 0.0074(7) 0.0016(7) C9 0.0136(9) 0.0138(10) 0.0171(10) 0.0006(8) 0.0043(8) -0.0010(8) C4 0.0132(9) 0.0130(10) 0.0106(9) 0.0007(8) 0.0021(7) 0.0005(8) C1 0.0161(10) 0.0104(10) 0.0142(10) -0.0005(8) 0.0071(8) -0.0019(8) C10 0.0148(10) 0.0143(10) 0.0163(10) 0.0022(8) 0.0033(8) 0.0025(8) C3 0.0099(9) 0.0143(10) 0.0127(9) 0.0001(8) 0.0024(7) -0.0025(8) C11 0.0107(9) 0.0171(10) 0.0149(10) -0.0011(8) 0.0027(8) 0.0021(8) N1 0.0109(8) 0.0146(9) 0.0129(8) -0.0002(7) 0.0030(7) 0.0004(7) C7 0.0158(10) 0.0229(12) 0.0130(10) 0.0067(9) -0.0010(8) -0.0050(9) C8 0.0146(9) 0.0110(10) 0.0152(10) 0.0002(8) 0.0077(8) -0.0007(8) C6 0.0123(9) 0.0216(11) 0.0163(10) 0.0045(9) -0.0005(8) -0.0068(8) C14 0.0126(9) 0.0187(11) 0.0150(10) 0.0005(9) 0.0009(8) 0.0026(8) C12 0.0131(10) 0.0312(14) 0.0265(12) 0.0117(11) 0.0004(9) -0.0057(10) C13 0.0139(10) 0.0274(13) 0.0252(12) 0.0130(10) -0.0005(9) -0.0043(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 O3 C8 1.256(3) . ? O3 Zn1 2.0441(17) 4_665 ? O2 C1 1.252(3) . ? O2 Zn1 2.0197(17) 3_655 ? O4 C8 1.244(3) . ? O4 Zn1 2.0556(17) 2_654 ? N2 C14 1.279(3) . ? N2 N2 1.407(4) 3_856 ? Zn1 O2 2.0197(17) 3_655 ? Zn1 O1 2.0314(16) . ? Zn1 N1 2.0393(19) . ? Zn1 O3 2.0441(17) 4_566 ? Zn1 O4 2.0556(17) 2_644 ? Zn1 Zn1 2.9885(4) 3_655 ? C5 C6 1.390(3) . ? C5 C4 1.396(3) . ? C5 C8 1.503(3) . ? C2 C3 1.392(3) . ? C2 C7 1.394(3) . ? C2 C1 1.503(3) . ? O1 C1 1.248(3) . ? C9 N1 1.342(3) . ? C9 C10 1.385(3) . ? C4 C3 1.384(3) . ? C10 C11 1.390(3) . ? C11 C12 1.389(3) . ? C11 C14 1.476(3) . ? N1 C13 1.341(3) . ? C7 C6 1.385(3) . ? C12 C13 1.379(3) . ? 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 C8 O3 Zn1 118.75(15) . 4_665 ? C1 O2 Zn1 121.33(15) . 3_655 ? C8 O4 Zn1 136.88(16) . 2_654 ? C14 N2 N2 111.4(2) . 3_856 ? O2 Zn1 O1 158.09(7) 3_655 . ? O2 Zn1 N1 101.44(7) 3_655 . ? O1 Zn1 N1 100.20(7) . . ? O2 Zn1 O3 90.34(9) 3_655 4_566 ? O1 Zn1 O3 87.82(8) . 4_566 ? N1 Zn1 O3 103.77(7) . 4_566 ? O2 Zn1 O4 87.14(8) 3_655 2_644 ? O1 Zn1 O4 86.54(9) . 2_644 ? N1 Zn1 O4 97.89(7) . 2_644 ? O3 Zn1 O4 158.26(7) 4_566 2_644 ? O2 Zn1 Zn1 84.35(5) 3_655 3_655 ? O1 Zn1 Zn1 73.75(5) . 3_655 ? N1 Zn1 Zn1 168.46(5) . 3_655 ? O3 Zn1 Zn1 86.02(5) 4_566 3_655 ? O4 Zn1 Zn1 72.25(5) 2_644 3_655 ? C6 C5 C4 119.41(19) . . ? C6 C5 C8 121.14(18) . . ? C4 C5 C8 119.40(18) . . ? C3 C2 C7 119.29(19) . . ? C3 C2 C1 121.32(18) . . ? C7 C2 C1 119.39(19) . . ? C1 O1 Zn1 135.09(15) . . ? N1 C9 C10 123.0(2) . . ? C3 C4 C5 120.73(19) . . ? O1 C1 O2 125.5(2) . . ? O1 C1 C2 116.90(19) . . ? O2 C1 C2 117.62(19) . . ? C9 C10 C11 118.8(2) . . ? C4 C3 C2 119.89(19) . . ? C12 C11 C10 118.2(2) . . ? C12 C11 C14 121.0(2) . . ? C10 C11 C14 120.8(2) . . ? C13 N1 C9 117.71(19) . . ? C13 N1 Zn1 119.60(15) . . ? C9 N1 Zn1 122.66(15) . . ? C6 C7 C2 120.9(2) . . ? O4 C8 O3 125.4(2) . . ? O4 C8 C5 116.84(19) . . ? O3 C8 C5 117.78(19) . . ? C7 C6 C5 119.80(19) . . ? N2 C14 C11 119.1(2) . . ? C13 C12 C11 119.3(2) . . ? N1 C13 C12 122.9(2) . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.65 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.486 _refine_diff_density_min -0.934 _refine_diff_density_rms 0.088 _database_code_depnum_ccdc_archive 'CCDC 944118' ####################################################################### # # 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_DG5 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C30 H22 N4 O8 Zn2' _chemical_formula_weight 697.26 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' Zn Zn 0.2839 1.4301 '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 7.7679(3) _cell_length_b 15.7170(6) _cell_length_c 12.0010(5) _cell_angle_alpha 90.00 _cell_angle_beta 98.3460(10) _cell_angle_gamma 90.00 _cell_volume 1449.66(10) _cell_formula_units_Z 2 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 250 _cell_measurement_theta_min 2.2 _cell_measurement_theta_max 26.4 _exptl_crystal_description Block _exptl_crystal_colour Yellow _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.597 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 708 _exptl_absorpt_coefficient_mu 1.713 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8973 _exptl_absorpt_correction_T_max 0.9856 _exptl_absorpt_process_details ; 'XPREP' - A PROGRAM DATA PREPARATION & RECIPROCAL SPACE EXPLORATION, Bruker Analytical X-ray Systems, 1997 ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(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 15003 _diffrn_reflns_av_R_equivalents 0.0441 _diffrn_reflns_av_unetI/netI 0.0341 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.15 _diffrn_reflns_theta_max 26.36 _reflns_number_total 2966 _reflns_number_gt 2211 _reflns_threshold_expression >2\s(I) _computing_data_collection 'SMART APEX II (Bruker,2010)' _computing_cell_refinement 'SMART APEX II' _computing_data_reduction 'SAINT (Bruker,2000)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Ortep-3v2 for windows (Farrugia, 1997)' _computing_publication_material 'PLATON (Spek, 2008)' _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^ > 2\s(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^+1.5942P] 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 2966 _refine_ls_number_parameters 199 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0489 _refine_ls_R_factor_gt 0.0318 _refine_ls_wR_factor_ref 0.0808 _refine_ls_wR_factor_gt 0.0731 _refine_ls_goodness_of_fit_ref 1.043 _refine_ls_restrained_S_all 1.043 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.2183(2) 0.10072(12) -0.02524(16) 0.0225(4) Uani 1 1 d . . . N1 N 0.3669(3) 0.01440(14) 0.20521(19) 0.0174(5) Uani 1 1 d . . . C1 C 0.1104(4) 0.12897(17) -0.1050(2) 0.0190(6) Uani 1 1 d . . . C2 C 0.1678(4) 0.20085(17) -0.1736(2) 0.0187(6) Uani 1 1 d . . . C11 C 0.6464(4) 0.03299(19) 0.3783(2) 0.0221(6) Uani 1 1 d . . . C9 C 0.3509(4) 0.06022(19) 0.2980(2) 0.0255(7) Uani 1 1 d . . . H9 H 0.2441 0.0853 0.3039 0.031 Uiso 1 1 calc R . . C13 C 0.5207(4) -0.02127(18) 0.1986(2) 0.0232(7) Uani 1 1 d . . . H13 H 0.5339 -0.0523 0.1344 0.028 Uiso 1 1 calc R . . C10 C 0.4866(4) 0.07149(19) 0.3849(2) 0.0244(6) Uani 1 1 d . . . H10 H 0.4714 0.1044 0.4471 0.029 Uiso 1 1 calc R . . N2 N 0.9279(3) -0.00599(19) 0.4584(2) 0.0346(7) Uani 1 1 d . . . C12 C 0.6608(4) -0.01421(19) 0.2827(2) 0.0241(7) Uani 1 1 d . . . H12 H 0.7651 -0.0412 0.2753 0.029 Uiso 1 1 calc R . . C14 C 0.7998(4) 0.0437(2) 0.4683(2) 0.0270(7) Uani 1 1 d . . . C15 C 0.7931(4) 0.1085(2) 0.5583(3) 0.0381(8) Uani 1 1 d . . . H15A H 0.9005 0.1076 0.6093 0.057 Uiso 1 1 calc R . . H15B H 0.6984 0.0956 0.5988 0.057 Uiso 1 1 calc R . . H15C H 0.7760 0.1639 0.5249 0.057 Uiso 1 1 calc R . . O2 O -0.0411(3) 0.10066(12) -0.13451(17) 0.0238(5) Uani 1 1 d . . . C4 C 0.1064(4) 0.30031(17) -0.3276(2) 0.0200(6) Uani 1 1 d . . . H4 H 0.0275 0.3246 -0.3844 0.024 Uiso 1 1 calc R . . C3 C 0.0509(4) 0.23920(17) -0.2578(2) 0.0200(6) Uani 1 1 d . . . H3 H -0.0657 0.2236 -0.2671 0.024 Uiso 1 1 calc R . . C5 C 0.2800(4) 0.32557(17) -0.3131(2) 0.0199(6) Uani 1 1 d . . . C8 C 0.3429(4) 0.39279(17) -0.3870(2) 0.0199(6) Uani 1 1 d . . . C7 C 0.3405(4) 0.22745(18) -0.1581(2) 0.0248(7) Uani 1 1 d . . . H7 H 0.4192 0.2037 -0.1007 0.030 Uiso 1 1 calc R . . C6 C 0.3958(4) 0.28887(18) -0.2271(3) 0.0241(7) Uani 1 1 d . . . H6 H 0.5117 0.3059 -0.2161 0.029 Uiso 1 1 calc R . . O3 O 0.4957(2) 0.41922(13) -0.35961(16) 0.0245(5) Uani 1 1 d . . . O4 O 0.2389(2) 0.41841(12) -0.47079(16) 0.0231(5) Uani 1 1 d . . . Zn1 Zn 0.16694(4) 0.001870(19) 0.07663(2) 0.01325(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 O1 0.0250(10) 0.0214(11) 0.0212(11) 0.0068(8) 0.0041(9) -0.0005(8) N1 0.0158(11) 0.0206(13) 0.0149(11) 0.0006(9) -0.0003(9) -0.0013(9) C1 0.0259(15) 0.0141(14) 0.0177(14) -0.0003(11) 0.0059(12) -0.0015(11) C2 0.0225(14) 0.0158(14) 0.0184(14) -0.0004(11) 0.0053(11) -0.0028(11) C11 0.0198(14) 0.0258(15) 0.0190(15) 0.0022(12) -0.0030(12) -0.0016(12) C9 0.0245(15) 0.0285(17) 0.0227(16) -0.0006(13) 0.0006(12) 0.0016(13) C13 0.0204(14) 0.0281(17) 0.0202(15) 0.0003(12) -0.0005(12) 0.0006(12) C10 0.0300(16) 0.0250(16) 0.0174(15) -0.0060(12) 0.0003(12) -0.0012(13) N2 0.0231(13) 0.0526(18) 0.0238(14) -0.0075(13) -0.0108(11) 0.0034(13) C12 0.0181(13) 0.0315(18) 0.0216(15) -0.0029(13) -0.0005(11) 0.0019(12) C14 0.0248(16) 0.0331(18) 0.0206(16) 0.0026(14) -0.0048(12) -0.0045(14) C15 0.0395(19) 0.036(2) 0.0328(19) -0.0072(15) -0.0136(15) 0.0032(15) O2 0.0256(11) 0.0202(11) 0.0254(11) 0.0052(9) 0.0025(9) -0.0083(8) C4 0.0218(14) 0.0188(14) 0.0188(15) 0.0024(12) 0.0016(11) -0.0038(11) C3 0.0213(14) 0.0178(14) 0.0210(15) -0.0014(12) 0.0036(12) -0.0045(11) C5 0.0246(15) 0.0159(14) 0.0200(15) 0.0002(11) 0.0054(12) -0.0026(11) C8 0.0250(15) 0.0163(14) 0.0194(15) -0.0007(12) 0.0066(12) -0.0006(12) C7 0.0242(15) 0.0240(16) 0.0248(16) 0.0059(13) -0.0014(13) -0.0035(12) C6 0.0194(14) 0.0250(16) 0.0271(17) 0.0053(13) 0.0003(12) -0.0059(12) O3 0.0235(11) 0.0261(11) 0.0241(11) 0.0041(9) 0.0047(9) -0.0077(9) O4 0.0231(10) 0.0231(11) 0.0238(11) 0.0086(9) 0.0053(9) -0.0008(8) Zn1 0.01319(15) 0.01342(16) 0.01264(16) -0.00023(13) 0.00015(11) -0.00012(13) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 O1 C1 1.258(3) . ? O1 Zn1 2.0516(19) . ? N1 C13 1.332(4) . ? N1 C9 1.347(4) . ? N1 Zn1 2.034(2) . ? C1 O2 1.260(3) . ? C1 C2 1.503(4) . ? C2 C7 1.391(4) . ? C2 C3 1.393(4) . ? C11 C12 1.384(4) . ? C11 C10 1.394(4) . ? C11 C14 1.497(4) . ? C9 C10 1.382(4) . ? C13 C12 1.378(4) . ? N2 C14 1.285(4) . ? N2 N2 1.401(5) 3_756 ? C14 C15 1.490(4) . ? O2 Zn1 2.0572(18) 3 ? C4 C3 1.384(4) . ? C4 C5 1.392(4) . ? C5 C6 1.392(4) . ? C5 C8 1.506(4) . ? C8 O3 1.255(3) . ? C8 O4 1.262(3) . ? C7 C6 1.381(4) . ? O3 Zn1 2.0465(19) 4_665 ? O4 Zn1 2.0344(19) 2_554 ? Zn1 O4 2.0344(19) 2_544 ? Zn1 O3 2.0465(19) 4_566 ? Zn1 O2 2.0572(18) 3 ? Zn1 Zn1 2.9544(5) 3 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 O1 Zn1 123.72(18) . . ? C13 N1 C9 117.7(2) . . ? C13 N1 Zn1 120.42(19) . . ? C9 N1 Zn1 121.83(19) . . ? O1 C1 O2 125.5(3) . . ? O1 C1 C2 117.7(2) . . ? O2 C1 C2 116.8(2) . . ? C7 C2 C3 118.8(3) . . ? C7 C2 C1 120.6(2) . . ? C3 C2 C1 120.6(2) . . ? C12 C11 C10 117.4(3) . . ? C12 C11 C14 120.5(3) . . ? C10 C11 C14 122.2(3) . . ? N1 C9 C10 122.7(3) . . ? N1 C13 C12 122.8(3) . . ? C9 C10 C11 119.3(3) . . ? C14 N2 N2 113.7(3) . 3_756 ? C13 C12 C11 120.0(3) . . ? N2 C14 C15 126.3(3) . . ? N2 C14 C11 114.2(3) . . ? C15 C14 C11 119.5(3) . . ? C1 O2 Zn1 130.69(18) . 3 ? C3 C4 C5 120.2(3) . . ? C4 C3 C2 120.8(3) . . ? C6 C5 C4 119.0(3) . . ? C6 C5 C8 119.8(2) . . ? C4 C5 C8 121.2(3) . . ? O3 C8 O4 125.1(3) . . ? O3 C8 C5 117.0(2) . . ? O4 C8 C5 117.9(2) . . ? C6 C7 C2 120.5(3) . . ? C7 C6 C5 120.7(3) . . ? C8 O3 Zn1 138.07(19) . 4_665 ? C8 O4 Zn1 117.19(17) . 2_554 ? N1 Zn1 O4 103.41(8) . 2_544 ? N1 Zn1 O3 97.11(8) . 4_566 ? O4 Zn1 O3 159.44(8) 2_544 4_566 ? N1 Zn1 O1 100.70(8) . . ? O4 Zn1 O1 89.86(8) 2_544 . ? O3 Zn1 O1 87.54(8) 4_566 . ? N1 Zn1 O2 99.65(8) . 3 ? O4 Zn1 O2 86.40(8) 2_544 3 ? O3 Zn1 O2 88.97(8) 4_566 3 ? O1 Zn1 O2 159.62(8) . 3 ? N1 Zn1 Zn1 168.23(7) . 3 ? O4 Zn1 Zn1 87.78(6) 2_544 3 ? O3 Zn1 Zn1 71.66(6) 4_566 3 ? O1 Zn1 Zn1 82.71(5) . 3 ? O2 Zn1 Zn1 77.14(6) 3 3 ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 26.36 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.905 _refine_diff_density_min -0.329 _refine_diff_density_rms 0.076 _database_code_depnum_ccdc_archive 'CCDC 944119'