# Electronic Supplementary Material for CrystEngComm # This journal is (c) The Royal Society of Chemistry 2009 data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 _publ_contact_author_name 'Luiz Fernando de Oliveira' _publ_contact_author_email LUIZ.OLIVEIRA@UFJF.EDU.BR _publ_section_title ; An Intriguing Hydrogen Bond Arrangement of Polymeric 1D Chains of 4,4'-Bipyridine Coordinated to Co2+, Ni2+, Cu2+ and Zn2+ Ions Having Barbiturate as Counterions in a 3D Network ; loop_ _publ_author_name 'Luiz Fernando de Oliveira' 'Renata Diniz' 'Humberto C. Garcia' 'Maria I. Yoshida' # Attachment 'hbcobi-ccdc2.cif' #----------------------------------------------------------------------------# # Global data block identification for start of deposition data_HBCOBI _database_code_depnum_ccdc_archive 'CCDC 702329' _audit_creation_date 'Dec 16 14:05:31 2008' _audit_creation_method 'WinGX routine CIF_UPDATE' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; 'tetraaquacobalt(II)-4,4'-bipyridine barbiturate hexahydrate' ; _chemical_name_common "'tetraaquacobalt(ii)-4,4'-bipyridine barbiturate hexahydrate'" _chemical_melting_point ? _chemical_formula_moiety 'C10 H16 Co N2 O4, 2(C4 H3 N2 O3), 6(H2 O)' _chemical_formula_sum 'C18 H34 Co N6 O16' _chemical_formula_weight 649.44 #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z' '-y, x-y, z+1/3' '-x+y, -x, z+2/3' 'x-y, x, z+2/3' 'y, -x+y, z+1/3' 'x-y, -y, -z' '-x, -x+y, -z+2/3' 'y, x, -z+1/3' '-y, -x, -z+1/3' 'x, x-y, -z+2/3' '-x+y, y, -z' _cell_length_a 11.641(1) _cell_length_b 11.641(1) _cell_length_c 18.756(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 2201.2(4) _cell_formula_units_Z 3 _cell_measurement_temperature 298(2) _symmetry_cell_setting Hexagonal _symmetry_space_group_name_Hall 'P 64 2c (0 0 -1)' _symmetry_space_group_name_H-M 'P 64 2 2' _symmetry_Int_Tables_number 181 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prismatic _exptl_crystal_colour 'light pink' _exptl_crystal_size_max 0.36 _exptl_crystal_size_mid 0.33 _exptl_crystal_size_min 0.23 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.467 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1005 #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist 1 0 1 0.0900 -1 1 1 0.1150 0 -1 1 0.1400 -1 0 1 0.1440 0 1 1 0.0860 1 -1 1 0.1100 0 0 -1 0.1580 0 -1 -1 0.2580 0 1 -2 0.1940 2 0 -3 0.2030 -1 0 -1 0.2470 _exptl_absorpt_coefficient_mu 0.6600 _exptl_absorpt_correction_type gaussian _exptl_absorpt_process_details ; a grid of 8 x 8 x 8 = 512 sampling points was used ; _exptl_absorpt_correction_T_min 0.8358 _exptl_absorpt_correction_T_max 0.8713 _exptl_absorpt_correction_T_ave 0.8558 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _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_reflns_number 17763 _diffrn_reflns_av_R_equivalents 0.0339 _diffrn_reflns_av_sigmaI/netI 0.0233 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 5.20 _diffrn_reflns_theta_max 27.56 _reflns_number_total 1674 _reflns_number_gt 1365 _reflns_threshold_expression >2sigma(I) _diffrn_measured_fraction_theta_max 0.979 _diffrn_reflns_theta_full 27.56 _diffrn_measured_fraction_theta_full 0.979 #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'COLLECT (Enraf-Nonius, 1997-2000)' _computing_cell_refinement 'DIRAX (Duisenberg, 1992)' _computing_data_reduction 'EVALCCD (Duisenber et al., 2003)' _computing_structure_solution 'SHELXL-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP 3 FOR WINDOWS (Farrugia, 1997)' _computing_publication_material 'PLATON (Spek, 1990)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.0250P)^2^+0.9641P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.03(4) _refine_ls_number_reflns 1674 _refine_ls_number_parameters 102 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0468 _refine_ls_R_factor_gt 0.0326 _refine_ls_wR_factor_ref 0.0771 _refine_ls_wR_factor_gt 0.0714 _refine_ls_goodness_of_fit_ref 1.112 _refine_ls_restrained_S_all 1.114 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.135 _refine_diff_density_min -0.235 _refine_diff_density_rms 0.037 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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' Co Co 0.3494 0.9721 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 Co1 Co 1.0000 1.0000 0.8333 0.03001(14) Uani 1 4 d S . . N1 N 1.0000 0.80817(19) 0.8333 0.0331(5) Uani 1 2 d S . . O1 O 0.85739(18) 0.91841(19) 0.91165(10) 0.0593(5) Uani 1 1 d . . . H1B H 0.8665 0.8671 0.9411 0.089 Uiso 1 1 d R . . H1A H 0.8001 0.9265 0.9163 0.089 Uiso 1 1 d R . . C3 C 1.0000 0.5643(2) 0.8333 0.0310(6) Uani 1 2 d S . . C2 C 1.1144(2) 0.6847(2) 0.84707(13) 0.0403(6) Uani 1 1 d . . . H2 H 1.1937 0.6868 0.8569 0.048 Uiso 1 1 calc R . . C1 C 1.1098(2) 0.8016(2) 0.84612(13) 0.0408(6) Uani 1 1 d . . . H1 H 1.1881 0.8805 0.8549 0.049 Uiso 1 1 calc R . . O2 O 0.86626(10) 0.73252(19) 1.0000 0.0421(5) Uani 1 2 d S . . C6 C 0.66562(16) 0.3312(3) 1.0000 0.0447(7) Uani 1 2 d S . . H6 H 0.6195 0.2390 1.0000 0.054 Uiso 1 2 calc SR . . C4 C 0.80479(14) 0.6096(3) 1.0000 0.0326(6) Uani 1 2 d S . . N2 N 0.67522(19) 0.53729(19) 0.98042(10) 0.0371(4) Uani 1 1 d . . . O3 O 0.48286(17) 0.34632(17) 0.95692(12) 0.0592(5) Uani 1 1 d . . . C5 C 0.6016(2) 0.3991(2) 0.97844(12) 0.0403(5) Uani 1 1 d . . . O4 O 0.6346(2) 0.9218(2) 0.94027(17) 0.0991(10) Uani 1 1 d . . . H4A H 0.5716 0.9308 0.9163 0.149 Uiso 1 1 d R . . H4B H 0.6057 0.8425 0.9550 0.149 Uiso 1 1 d R . . O5 O 1.5000 1.0000 0.8541(2) 0.165(2) Uani 1 2 d SD . . H5A H 1.4337 0.9724 0.8316 0.247 Uiso 1 1 d RD . . H2N H 0.636(3) 0.578(2) 0.9696(13) 0.041(7) Uiso 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 Co1 0.0274(3) 0.02150(19) 0.0431(3) 0.000 0.000 0.01372(15) N1 0.0326(12) 0.0236(8) 0.0462(13) 0.0002(7) 0.0004(14) 0.0163(6) O1 0.0580(11) 0.0636(13) 0.0769(12) 0.0342(11) 0.0292(10) 0.0457(11) C3 0.0354(15) 0.0251(10) 0.0358(14) 0.0016(8) 0.0031(16) 0.0177(7) C2 0.0330(12) 0.0297(11) 0.0639(16) -0.0047(11) -0.0075(11) 0.0198(10) C1 0.0342(11) 0.0243(10) 0.0647(16) -0.0050(10) -0.0075(11) 0.0153(9) O2 0.0396(9) 0.0240(10) 0.0574(13) 0.000 -0.0080(11) 0.0120(5) C6 0.0275(10) 0.0248(15) 0.081(2) 0.000 -0.0029(14) 0.0124(8) C4 0.0305(10) 0.0289(14) 0.0378(14) 0.000 0.0002(13) 0.0144(7) N2 0.0292(10) 0.0262(9) 0.0601(13) -0.0044(8) -0.0085(8) 0.0171(8) O3 0.0326(10) 0.0329(10) 0.1154(15) -0.0165(9) -0.0247(10) 0.0188(8) C5 0.0293(12) 0.0300(12) 0.0629(13) -0.0061(11) -0.0042(11) 0.0157(9) O4 0.0496(13) 0.0446(12) 0.206(3) 0.0375(15) 0.0474(15) 0.0260(11) O5 0.200(6) 0.262(7) 0.078(2) 0.000 0.000 0.150(6) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 Co1 O1 2.0586(16) 11_566 ? Co1 O1 2.0586(16) 8_766 ? Co1 O1 2.0586(16) 2_775 ? Co1 O1 2.0586(16) . ? Co1 N1 2.234(2) . ? Co1 N1 2.234(2) 2_775 ? N1 C1 1.340(3) 8_766 ? N1 C1 1.340(3) . ? C3 C2 1.391(3) 8_766 ? C3 C2 1.391(3) . ? C3 C3 1.498(5) 2_765 ? C2 C1 1.388(3) . ? O2 C4 1.238(3) . ? C6 C5 1.390(3) 12_657 ? C6 C5 1.390(3) . ? C4 N2 1.361(3) . ? C4 N2 1.361(2) 12_657 ? N2 C5 1.393(3) . ? O3 C5 1.265(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 O1 Co1 O1 88.92(11) 11_566 8_766 ? O1 Co1 O1 173.34(10) 11_566 2_775 ? O1 Co1 O1 91.46(11) 8_766 2_775 ? O1 Co1 O1 91.46(11) 11_566 . ? O1 Co1 O1 173.34(10) 8_766 . ? O1 Co1 O1 88.92(11) 2_775 . ? O1 Co1 N1 93.33(5) 11_566 . ? O1 Co1 N1 86.67(5) 8_766 . ? O1 Co1 N1 93.33(5) 2_775 . ? O1 Co1 N1 86.67(5) . . ? O1 Co1 N1 86.67(5) 11_566 2_775 ? O1 Co1 N1 93.33(5) 8_766 2_775 ? O1 Co1 N1 86.67(5) 2_775 2_775 ? O1 Co1 N1 93.33(5) . 2_775 ? N1 Co1 N1 180.000(1) . 2_775 ? C1 N1 C1 115.5(2) 8_766 . ? C1 N1 Co1 122.26(12) 8_766 . ? C1 N1 Co1 122.26(12) . . ? C2 C3 C2 116.2(2) 8_766 . ? C2 C3 C3 121.89(13) 8_766 2_765 ? C2 C3 C3 121.89(12) . 2_765 ? C1 C2 C3 119.9(2) . . ? N1 C1 C2 124.2(2) . . ? C5 C6 C5 121.1(3) 12_657 . ? O2 C4 N2 122.46(13) . . ? O2 C4 N2 122.46(13) . 12_657 ? N2 C4 N2 115.1(3) . 12_657 ? C4 N2 C5 125.00(19) . . ? O3 C5 C6 125.6(2) . . ? O3 C5 N2 117.48(19) . . ? C6 C5 N2 116.9(2) . . ? 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 O1 Co1 N1 C1 -122.07(15) . . . . no O1 Co1 N1 C1 57.92(15) . . . 8_766 no O1 Co1 N1 C1 -33.35(15) 2_775 . . . no O1 Co1 N1 C1 146.65(15) 11_566 . . . no Co1 N1 C1 C2 179.68(17) . . . . no C1 N1 C1 C2 -0.3(3) . . 8_766 8_766 no C5 N2 C4 O2 179.04(16) . . . . no C5 N2 C4 N2 -1.0(3) . . . 12_657 no C4 N2 C5 O3 -177.9(2) . . . . no C4 N2 C5 C6 1.8(3) . . . . no N1 C1 C2 C3 0.6(3) . . . . no C1 C2 C3 C3 179.71(16) . . . 2_765 no C1 C2 C3 C2 -0.3(3) . . . 8_766 no O3 C5 C6 C5 178.9(2) . . . 12_657 no N2 C5 C6 C5 -0.8(3) . . . 12_657 no loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A _geom_hbond_publ_flag # #D H A D - H H...A D...A D - H...A symm(A) # O1 H1A O4 0.7200 1.9500 2.670(5) 170.00 . yes O1 H1B O2 0.8600 1.9200 2.769(3) 172.00 . yes N2 H2N O3 0.84(4) 1.98(4) 2.813(4) 171(3) 2_665 yes O4 H4A O5 0.9100 1.8500 2.706(4) 159.00 1_455 yes O4 H4B O3 0.8500 1.9100 2.728(3) 161.00 2_665 yes # #END # # Attachment 'hbnibi-ccdc2.cif' #----------------------------------------------------------------------------# # Global data block identification for start of deposition data_HBNIBI _database_code_depnum_ccdc_archive 'CCDC 702330' _audit_creation_date 'Dec 17 16:01:44 2008' _audit_creation_method 'WinGX routine CIF_UPDATE' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; 'tetraaquanickel(II)-4,4'-bipyridine barbiturate hexahydrate' ; _chemical_name_common "'tetraaquanickel(ii)-4,4'-bipyridine barbiturate hexahydrate'" _chemical_melting_point ? _chemical_formula_moiety 'C10 H16 N2 Ni O4, 2(C4 H3 N2 O3), 6(H2 O)' _chemical_formula_sum 'C18 H34 N6 Ni O16' _chemical_formula_weight 649.22 #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' '-y, -x, -z+1/6' 'y, x, -z+2/3' 'x-y, -y, -z' '-x+y, y, -z+1/2' 'x, x-y, -z+5/6' '-x, -x+y, -z+1/3' '-y, x-y, z+2/3' 'y, -x+y, z+1/6' 'x-y, x, z+5/6' '-x+y, -x, z+1/3' _cell_length_a 11.453(2) _cell_length_b 11.453(2) _cell_length_c 36.912(4) _cell_angle_alpha 90.000 _cell_angle_beta 90.000 _cell_angle_gamma 120.000 _cell_volume 4193(3) _cell_formula_units_Z 6 _cell_measurement_temperature 298(2) _symmetry_cell_setting Hexagonal _symmetry_space_group_name_Hall 'P 65 2 ( 0 0 1)' _symmetry_space_group_name_H-M 'P 65 2 2' _symmetry_Int_Tables_number 179 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prismatic _exptl_crystal_colour green _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.27 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.543 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2040 #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.7800 _exptl_absorpt_correction_type gaussian _exptl_absorpt_process_details ; a grid of 8 x 8 x 8 = 512 sampling points was used ; _exptl_absorpt_correction_T_min 0.7903 _exptl_absorpt_correction_T_max 0.9007 _exptl_absorpt_correction_T_ave 0.8516 loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist 2 0 -3 0.1490 0 2 -3 0.1540 0 0 1 0.0600 0 0 -1 0.0910 -1 2 -3 0.1760 -2 2 -3 0.1690 -1 0 -1 0.1820 0 -1 2 0.1080 1 -1 1 0.1650 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _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_reflns_number 16434 _diffrn_reflns_av_R_equivalents 0.0474 _diffrn_reflns_av_sigmaI/netI 0.0501 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -47 _diffrn_reflns_limit_l_max 47 _diffrn_reflns_theta_min 5.25 _diffrn_reflns_theta_max 27.49 _reflns_number_total 3137 _reflns_number_gt 2401 _reflns_threshold_expression >2sigma(I) _diffrn_measured_fraction_theta_max 0.981 _diffrn_reflns_theta_full 0.50 _diffrn_measured_fraction_theta_full 0.000 #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'COLLECT (Enraf-Nonius, 1997-2000)' _computing_cell_refinement 'DIRAX (Duisenberg, 1992)' _computing_data_reduction 'EVALCCD (Duisenber et al., 2003)' _computing_structure_solution 'SHELXL-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP 3 FOR WINDOWS (Farrugia, 1997)' _computing_publication_material 'PLATON (Spek, 1990)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.0614P)^2^+2.7232P] 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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef none _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.05(3) _refine_ls_number_reflns 3137 _refine_ls_number_parameters 203 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0773 _refine_ls_R_factor_gt 0.0512 _refine_ls_wR_factor_ref 0.1284 _refine_ls_wR_factor_gt 0.1150 _refine_ls_goodness_of_fit_ref 1.038 _refine_ls_restrained_S_all 1.038 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.469 _refine_diff_density_min -0.350 _refine_diff_density_rms 0.056 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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' Ni Ni 0.3393 1.1124 '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' 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 Ni Ni 0.06979(5) 0.0000 0.0000 0.03197(19) Uani 1 2 d S . . N1 N -0.1183(3) 0.0000 0.0000 0.0338(9) Uani 1 2 d S . . N2 N -0.7432(3) 0.0000 0.0000 0.0358(10) Uani 1 2 d S . . N3 N 0.3574(3) 0.8275(4) 0.09500(9) 0.0444(8) Uani 1 1 d . . . H3N H 0.3964 0.9101 0.1020 0.053 Uiso 1 1 calc R . . N4 N 0.7065(3) 0.1046(3) 0.09379(9) 0.0432(8) Uani 1 1 d . . . H4N H 0.6668 0.0217 0.1006 0.052 Uiso 1 1 calc R . . O1 O -0.0139(3) -0.1691(3) 0.03206(7) 0.0446(7) Uani 1 1 d . . . H1A H 0.0365 -0.1673 0.0493 0.067 Uiso 1 1 d R . . H1B H -0.0373 -0.2386 0.0205 0.067 Uiso 1 1 d R . . O2 O 0.1229(3) 0.1183(3) 0.04612(6) 0.0501(7) Uani 1 1 d . . . H2A H 0.2021 0.1716 0.0527 0.075 Uiso 1 1 d R . . H2B H 0.0609 0.1236 0.0559 0.075 Uiso 1 1 d R . . O3 O 0.1662(2) 0.8338(2) 0.0833 0.0489(12) Uani 1 2 d S . . O4 O 0.5496(3) 0.8268(4) 0.10971(12) 0.0849(13) Uani 1 1 d . . . O5 O 0.90033(18) 0.09967(18) 0.0833 0.0375(9) Uani 1 2 d S . . O6 O 0.5112(4) 0.1073(4) 0.10459(14) 0.0959(14) Uani 1 1 d . . . O7 O 0.3680(4) 0.2562(6) 0.08002(12) 0.1202(19) Uani 1 1 d . . . H7A H 0.4028 0.2189 0.0864 0.180 Uiso 1 1 d R . . H7B H 0.4197 0.3208 0.0665 0.180 Uiso 1 1 d R . . O8 O 0.9186(7) 0.5978(5) -0.00422(15) 0.066(3) Uani 0.601(13) 1 d P . . H8A H 0.9145 0.5710 0.0120 0.099 Uiso 1 1 d R . . H8B H 0.8719 0.5862 -0.0178 0.099 Uiso 1 1 d R . . O8A O 0.7966(18) 0.5884(13) 0.0087(5) 0.139(9) Uani 0.399(13) 1 d P . . O9 O 0.5812(8) 0.5114(9) 0.02498(18) 0.197(3) Uani 1 1 d . . . H9A H 0.4998 0.4772 0.0183 0.296 Uiso 1 1 d R . . H9B H 0.6359 0.5628 0.0432 0.296 Uiso 1 1 d R . . C1 C -0.2334(4) -0.1061(4) 0.01192(10) 0.0408(10) Uani 1 1 d . . . H1 H -0.2306 -0.1812 0.0204 0.049 Uiso 1 1 calc R . . C2 C -0.3561(4) -0.1094(4) 0.01227(10) 0.0411(10) Uani 1 1 d . . . H2 H -0.4327 -0.1858 0.0208 0.049 Uiso 1 1 calc R . . C3 C -0.3658(4) 0.0000 0.0000 0.0344(11) Uani 1 2 d S . . C4 C -0.7386(4) -0.1141(4) -0.00420(11) 0.0413(9) Uani 1 1 d . . . H4 H -0.8195 -0.1945 -0.0072 0.050 Uiso 1 1 calc R . . C5 C -0.6193(4) -0.1183(4) -0.00428(10) 0.0410(9) Uani 1 1 d . . . H5 H -0.6217 -0.2000 -0.0072 0.049 Uiso 1 1 calc R . . C6 C -0.4963(4) 0.0000 0.0000 0.0360(12) Uani 1 2 d S . . C7 C 0.2288(3) 0.7712(3) 0.0833 0.0352(13) Uani 1 2 d S . . C8 C 0.4317(5) 0.7616(5) 0.09660(13) 0.0569(12) Uani 1 1 d . . . C9 C 0.3694(3) 0.6306(3) 0.0833 0.068(2) Uani 1 2 d S . . H9 H 0.4163 0.5838 0.0833 0.082 Uiso 1 2 calc SR . . C10 C 0.8380(3) 0.1620(3) 0.0833 0.0328(13) Uani 1 2 d S . . C11 C 0.6307(5) 0.1703(5) 0.09424(15) 0.0635(14) Uani 1 1 d . . . C12 C 0.6963(4) 0.3037(4) 0.0833 0.082(3) Uani 1 2 d S . . H12 H 0.6493 0.3505 0.0833 0.098 Uiso 1 2 calc SR . . 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 Ni 0.0230(2) 0.0367(4) 0.0408(3) -0.0018(3) -0.00090(14) 0.0184(2) N1 0.0267(15) 0.036(3) 0.0417(19) -0.0029(19) -0.0014(10) 0.0180(13) N2 0.0276(16) 0.043(3) 0.042(2) -0.006(2) -0.0029(11) 0.0215(14) N3 0.039(2) 0.040(2) 0.0593(19) -0.0020(15) -0.0028(16) 0.0229(17) N4 0.036(2) 0.034(2) 0.0582(19) -0.0062(15) 0.0031(16) 0.0160(17) O1 0.0350(15) 0.0452(17) 0.0555(14) 0.0058(12) -0.0052(12) 0.0214(14) O2 0.0331(15) 0.065(2) 0.0549(14) -0.0192(13) -0.0029(11) 0.0261(14) O3 0.056(2) 0.056(2) 0.049(2) -0.0103(17) -0.0103(17) 0.038(3) O4 0.036(2) 0.059(2) 0.156(4) 0.028(2) -0.013(2) 0.0206(18) O5 0.0304(17) 0.0304(17) 0.055(2) 0.0047(13) 0.0047(13) 0.0176(19) O6 0.037(2) 0.070(3) 0.176(4) -0.040(3) 0.013(2) 0.023(2) O7 0.070(3) 0.141(5) 0.111(3) -0.028(3) -0.008(3) 0.023(3) O8 0.076(5) 0.058(4) 0.064(4) -0.010(3) -0.023(3) 0.035(3) O8A 0.142(17) 0.084(9) 0.183(14) 0.013(9) -0.054(13) 0.050(9) O9 0.182(7) 0.261(9) 0.165(5) -0.079(6) -0.068(5) 0.123(7) C1 0.030(2) 0.035(2) 0.064(2) 0.0064(17) -0.0003(16) 0.0214(19) C2 0.026(2) 0.041(2) 0.058(2) 0.0050(18) 0.0028(16) 0.0183(19) C3 0.0264(18) 0.046(3) 0.037(2) -0.004(2) -0.0021(12) 0.0228(17) C4 0.028(2) 0.040(2) 0.059(2) -0.0040(19) -0.0039(18) 0.0190(18) C5 0.0292(19) 0.044(2) 0.058(2) -0.0130(18) -0.0064(19) 0.0248(18) C6 0.029(2) 0.052(3) 0.034(2) 0.000(2) -0.0002(12) 0.0262(17) C7 0.036(2) 0.036(2) 0.035(2) -0.0011(18) -0.0011(18) 0.019(3) C8 0.033(3) 0.050(3) 0.093(3) 0.027(2) 0.011(2) 0.026(2) C9 0.040(3) 0.040(3) 0.128(6) 0.021(3) 0.021(3) 0.022(4) C10 0.028(2) 0.028(2) 0.036(3) -0.0048(18) -0.0048(18) 0.010(3) C11 0.038(3) 0.045(3) 0.104(4) -0.030(3) -0.008(3) 0.017(3) C12 0.045(4) 0.045(4) 0.168(8) -0.037(4) -0.037(4) 0.031(4) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 Ni O1 2.051(3) 5 ? Ni O1 2.051(3) . ? Ni O2 2.071(2) . ? Ni O2 2.071(2) 5 ? Ni N2 2.140(4) 1_655 ? Ni N1 2.152(4) . ? N1 C1 1.343(4) . ? N1 C1 1.344(4) 5 ? N2 C4 1.343(4) 5 ? N2 C4 1.344(4) . ? N2 Ni 2.140(4) 1_455 ? N3 C7 1.350(4) . ? N3 C8 1.392(6) . ? N4 C10 1.362(4) . ? N4 C11 1.406(6) . ? O3 C7 1.241(7) . ? O4 C8 1.268(6) . ? O5 C10 1.236(6) . ? O6 C11 1.244(6) . ? O8 O8A 1.427(19) . ? C1 C2 1.386(5) . ? C2 C3 1.389(5) . ? C3 C2 1.388(5) 5 ? C3 C6 1.493(7) . ? C4 C5 1.390(5) . ? C5 C6 1.392(5) . ? C6 C5 1.393(5) 5 ? C7 N3 1.351(4) 3_665 ? C8 C9 1.390(6) . ? C9 C8 1.389(6) 3_665 ? C10 N4 1.364(4) 3_665 ? C11 C12 1.383(6) . ? C12 C11 1.381(6) 3_665 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 Ni O1 179.46(15) 5 . ? O1 Ni O2 90.55(11) 5 . ? O1 Ni O2 89.46(11) . . ? O1 Ni O2 89.46(11) 5 5 ? O1 Ni O2 90.56(11) . 5 ? O2 Ni O2 176.18(16) . 5 ? O1 Ni N2 89.83(7) 5 1_655 ? O1 Ni N2 89.64(7) . 1_655 ? O2 Ni N2 91.87(8) . 1_655 ? O2 Ni N2 91.94(8) 5 1_655 ? O1 Ni N1 90.17(7) 5 . ? O1 Ni N1 90.36(7) . . ? O2 Ni N1 88.13(8) . . ? O2 Ni N1 88.06(8) 5 . ? N2 Ni N1 180.0 1_655 . ? C1 N1 C1 116.2(4) . 5 ? C1 N1 Ni 121.9(2) . . ? C1 N1 Ni 122.0(2) 5 . ? C4 N2 C4 116.6(4) 5 . ? C4 N2 Ni 121.6(2) 5 1_455 ? C4 N2 Ni 121.7(2) . 1_455 ? C7 N3 C8 124.8(4) . . ? C10 N4 C11 125.0(4) . . ? N1 C1 C2 123.3(4) . . ? C1 C2 C3 120.7(4) . . ? C2 C3 C2 115.8(5) 5 . ? C2 C3 C6 122.1(2) 5 . ? C2 C3 C6 122.2(2) . . ? N2 C4 C5 123.4(4) . . ? C4 C5 C6 120.0(4) . . ? C5 C6 C5 116.6(5) . 5 ? C5 C6 C3 121.7(2) . . ? C5 C6 C3 121.7(2) 5 . ? O3 C7 N3 122.1(3) . . ? O3 C7 N3 122.2(3) . 3_665 ? N3 C7 N3 115.8(5) . 3_665 ? O4 C8 C9 126.3(5) . . ? O4 C8 N3 117.1(4) . . ? C9 C8 N3 116.6(4) . . ? C8 C9 C8 121.3(6) 3_665 . ? O5 C10 N4 122.6(2) . . ? O5 C10 N4 122.7(2) . 3_665 ? N4 C10 N4 114.7(5) . 3_665 ? O6 C11 C12 124.1(5) . . ? O6 C11 N4 119.1(5) . . ? C12 C11 N4 116.7(5) . . ? C11 C12 C11 121.8(6) 3_665 . ? 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 O1 Ni N1 C1 -12.5(2) . . . . no O1 Ni N1 C1 167.5(2) . . . 5_555 no O2 Ni N1 C1 -101.9(2) . . . . no O2 Ni N1 C1 78.1(2) . . . 5_555 no O1 Ni N1 C1 167.5(2) 5_555 . . . no O1 Ni N2 C4 137.0(2) . . . 5_555 no O1 Ni N2 C4 -43.0(2) . . . . no O2 Ni N2 C4 47.6(2) . . . 5_555 no O2 Ni N2 C4 -132.4(2) . . . . no Ni N1 C1 C2 -179.9(3) . . . . no C1 N1 C1 C2 0.2(5) 5_555 . . . no C8 N3 C7 N3 -1.8(5) . . . 3_665 no C7 N3 C8 O4 -177.0(4) . . . . no C7 N3 C8 C9 3.5(6) . . . . no C8 N3 C7 O3 178.2(3) . . . . no C10 N4 C11 C12 -0.4(6) . . . . no C11 N4 C10 O5 -179.8(3) . . . . no C11 N4 C10 N4 0.2(5) . . . 3_665 no C10 N4 C11 O6 -179.6(4) . . . . no N1 C1 C2 C3 -0.1(6) . . . . no C1 C2 C3 C2 0.1(5) . . . 5_555 no C1 C2 C3 C6 -180.0(3) . . . 1_455 no O4 C8 C9 C8 179.0(5) . . . 3_665 no N3 C8 C9 C8 -1.6(6) . . . 3_665 no O6 C11 C12 C11 179.3(5) . . . 3_665 no N4 C11 C12 C11 0.2(6) . . . 3_665 no loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A _geom_hbond_publ_flag # #D H A D - H H...A D...A D - H...A symm(A) # O1 H1A O3 0.8500 1.9400 2.787(3) 172.00 3_655 yes O1 H1B O8 0.8200 1.9100 2.730(9) 175.00 1_445 yes O2 H2A O7 0.8400 1.9300 2.740(5) 162.00 . yes O2 H2B O5 0.8200 2.0000 2.808(3) 168.00 3_565 yes N3 H3N O6 0.8600 1.9700 2.802(7) 164.00 1_565 yes O7 H7A O6 0.7500 2.2800 3.036(7) 179.00 . yes O7 H7B O9 0.8400 2.5500 3.391(10) 178.00 . yes O8 H8B O4 0.6900 2.1100 2.807(10) 177.00 11_654 yes O9 H9A O8 0.8500 1.8600 2.706(14) 179.00 5_565 yes C1 H1 O1 0.9300 2.4500 3.034(6) 121.00 . yes # #END # # #END # # Attachment 'hbcubi-ccdc2.cif' #----------------------------------------------------------------------------# # Global data block identification for start of deposition data_HBCUBI _database_code_depnum_ccdc_archive 'CCDC 702331' _audit_creation_date 'Dec 17 16:02:39 2008' _audit_creation_method 'WinGX routine CIF_UPDATE' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; 'tetraaquacopper(II)-4,4'-bipyridine barbiturate hexahydrate' ; _chemical_name_common "'tetraaquacopper(ii)-4,4'-bipyridine barbiturate hexahydrate'" _chemical_melting_point ? _chemical_formula_moiety 'C10 H16 Cu N2 O4, 2(C4 H3 N2 O3), 6(H2 O)' _chemical_formula_sum 'C18 H34 Cu N6 O16' _chemical_formula_weight 654.05 #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' '-y, -x, -z+1/6' 'y, x, -z+2/3' 'x-y, -y, -z' '-x+y, y, -z+1/2' 'x, x-y, -z+5/6' '-x, -x+y, -z+1/3' '-y, x-y, z+2/3' 'y, -x+y, z+1/6' 'x-y, x, z+5/6' '-x+y, -x, z+1/3' _cell_length_a 11.467(2) _cell_length_b 11.467(2) _cell_length_c 36.974(3) _cell_angle_alpha 90.000 _cell_angle_beta 90.000 _cell_angle_gamma 120.000 _cell_volume 4210.1(11) _cell_formula_units_Z 6 _cell_measurement_temperature 298(2) _symmetry_cell_setting Hexagonal _symmetry_space_group_name_Hall 'P 65 2 ( 0 0 1)' _symmetry_space_group_name_H-M 'P 65 2 2' _symmetry_Int_Tables_number 179 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prismatic _exptl_crystal_colour blue _exptl_crystal_size_max 0.37 _exptl_crystal_size_mid 0.33 _exptl_crystal_size_min 0.29 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.548 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2046 #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.8600 _exptl_absorpt_correction_type gaussian loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist -1 0 0 0.1190 -1 1 -1 0.1530 1 1 -1 0.1940 0 0 1 0.2400 3 -2 0 0.1060 0 0 -1 0.1390 -1 1 4 0.1470 0 1 2 0.1350 2 -5 -1 0.1700 1 -2 6 0.2070 _exptl_absorpt_process_details ; a grid of 8 x 8 x 8 = 512 sampling points was used ; _exptl_absorpt_correction_T_min 0.8044 _exptl_absorpt_correction_T_max 0.8464 _exptl_absorpt_correction_T_ave 0.8274 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _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_reflns_number 26411 _diffrn_reflns_av_R_equivalents 0.0436 _diffrn_reflns_av_sigmaI/netI 0.0400 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -45 _diffrn_reflns_limit_l_max 47 _diffrn_reflns_theta_min 5.25 _diffrn_reflns_theta_max 27.49 _reflns_number_total 3141 _reflns_number_gt 2494 _reflns_threshold_expression >2sigma(I) _diffrn_measured_fraction_theta_max 0.982 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.982 #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'COLLECT (Enraf-Nonius, 1997-2000)' _computing_cell_refinement 'DIRAX (Duisenberg, 1992)' _computing_data_reduction 'EVALCCD (Duisenber et al., 2003)' _computing_structure_solution 'SHELXL-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP 3 FOR WINDOWS (Farrugia, 1997)' _computing_publication_material 'PLATON (Spek, 1990)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.0742P)^2^+3.5657P] 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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef none _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.10(2) _refine_ls_number_reflns 3141 _refine_ls_number_parameters 202 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0734 _refine_ls_R_factor_gt 0.0532 _refine_ls_wR_factor_ref 0.1448 _refine_ls_wR_factor_gt 0.1324 _refine_ls_goodness_of_fit_ref 1.072 _refine_ls_restrained_S_all 1.072 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.489 _refine_diff_density_min -0.327 _refine_diff_density_rms 0.069 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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' 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 0.07071(5) 0.0000 0.0000 0.0334(2) Uani 1 2 d S . . N1 N -0.1174(4) 0.0000 0.0000 0.0323(10) Uani 1 2 d S . . N2 N -0.7420(4) 0.0000 0.0000 0.0342(10) Uani 1 2 d S . . N3 N 0.3580(4) 0.8275(4) 0.09502(10) 0.0420(9) Uani 1 1 d . . . H3N H 0.3969 0.9101 0.1020 0.050 Uiso 1 1 calc R . . N4 N 0.7067(4) 0.1041(3) 0.09369(10) 0.0402(8) Uani 1 1 d . . . H4N H 0.6667 0.0212 0.1004 0.048 Uiso 1 1 calc R . . O1 O -0.0133(3) -0.1697(3) 0.03203(7) 0.0408(7) Uani 1 1 d . . . H1A H 0.0372 -0.1679 0.0493 0.061 Uiso 1 1 d R . . H1B H -0.0366 -0.2391 0.0204 0.061 Uiso 1 1 d R . . O2 O 0.1240(3) 0.1186(3) 0.04616(7) 0.0471(7) Uani 1 1 d . . . H2A H 0.2032 0.1719 0.0527 0.071 Uiso 1 1 d R . . H2B H 0.0620 0.1239 0.0559 0.071 Uiso 1 1 d R . . O3 O 0.1664(2) 0.8336(2) 0.0833 0.0445(11) Uani 1 2 d S . . O4 O 0.5497(3) 0.8262(4) 0.10961(13) 0.0811(14) Uani 1 1 d . . . O5 O 0.90066(18) 0.09934(18) 0.0833 0.0358(9) Uani 1 2 d S . . O6 O 0.5114(4) 0.1063(4) 0.10448(15) 0.0902(15) Uani 1 1 d . . . O7 O 0.3697(5) 0.2549(6) 0.08017(14) 0.1055(17) Uani 1 1 d . . . H7A H 0.4045 0.2175 0.0865 0.158 Uiso 1 1 d R . . H7B H 0.4214 0.3194 0.0666 0.158 Uiso 1 1 d R . . O8 O 0.9200(7) 0.5979(6) -0.00429(17) 0.062(2) Uani 0.638(15) 1 d P . . H8A H 0.9160 0.5711 0.0119 0.093 Uiso 1 1 d R . . H8B H 0.8734 0.5863 -0.0179 0.093 Uiso 1 1 d R . . O8A O 0.802(2) 0.5889(15) 0.0083(5) 0.130(11) Uani 0.362(15) 1 d P . . O9 O 0.5837(9) 0.5139(10) 0.0248(2) 0.187(4) Uani 1 1 d . . . H9A H 0.5022 0.4797 0.0181 0.281 Uiso 1 1 d R . . H9B H 0.6384 0.5653 0.0430 0.281 Uiso 1 1 d R . . C1 C -0.2327(4) -0.1065(4) 0.01185(12) 0.0403(10) Uani 1 1 d . . . H1 H -0.2298 -0.1815 0.0202 0.048 Uiso 1 1 calc R . . C2 C -0.3555(4) -0.1100(4) 0.01223(12) 0.0397(10) Uani 1 1 d . . . H2 H -0.4320 -0.1863 0.0207 0.048 Uiso 1 1 calc R . . C3 C -0.3649(4) 0.0000 0.0000 0.0312(11) Uani 1 2 d S . . C4 C -0.6230(4) 0.1147(4) 0.00415(12) 0.0380(9) Uani 1 1 d . . . H4 H -0.6235 0.1950 0.0071 0.046 Uiso 1 1 calc R . . C5 C -0.4991(4) 0.1189(4) 0.00426(11) 0.0390(9) Uani 1 1 d . . . H5 H -0.4195 0.2003 0.0071 0.047 Uiso 1 1 calc R . . C6 C -0.4959(4) 0.0000 0.0000 0.0325(12) Uani 1 2 d S . . C7 C 0.2292(3) 0.7708(3) 0.0833 0.0343(13) Uani 1 2 d S . . C8 C 0.4324(5) 0.7613(5) 0.09659(15) 0.0549(13) Uani 1 1 d . . . C9 C 0.3696(3) 0.6304(3) 0.0833 0.066(2) Uani 1 2 d S . . H9 H 0.4164 0.5836 0.0833 0.080 Uiso 1 2 calc SR . . C10 C 0.8386(3) 0.1614(3) 0.0833 0.0308(12) Uani 1 2 d S . . C11 C 0.6317(5) 0.1705(5) 0.09418(16) 0.0608(15) Uani 1 1 d . . . C12 C 0.6965(4) 0.3035(4) 0.0833 0.077(3) Uani 1 2 d S . . H12 H 0.6496 0.3503 0.0833 0.093 Uiso 1 2 calc SR . . 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 0.0240(3) 0.0365(4) 0.0440(3) -0.0016(3) -0.00081(15) 0.0183(2) N1 0.0260(15) 0.038(3) 0.037(2) -0.005(2) -0.0023(10) 0.0188(13) N2 0.0239(15) 0.043(3) 0.042(2) -0.007(2) -0.0036(12) 0.0213(14) N3 0.036(2) 0.0343(19) 0.060(2) -0.0012(16) -0.0038(17) 0.0206(17) N4 0.034(2) 0.0300(19) 0.054(2) -0.0065(15) 0.0027(16) 0.0140(16) O1 0.0321(15) 0.0396(16) 0.0526(16) 0.0048(12) -0.0057(13) 0.0194(14) O2 0.0284(14) 0.059(2) 0.0557(16) -0.0169(14) -0.0031(12) 0.0234(13) O3 0.049(2) 0.049(2) 0.047(2) -0.0099(18) -0.0099(18) 0.033(2) O4 0.0324(19) 0.053(2) 0.152(4) 0.028(3) -0.014(2) 0.0173(17) O5 0.0274(16) 0.0274(16) 0.055(2) 0.0034(14) 0.0034(14) 0.0152(18) O6 0.034(2) 0.065(3) 0.167(4) -0.037(3) 0.013(2) 0.0210(19) O7 0.062(3) 0.118(5) 0.109(4) -0.017(3) -0.008(3) 0.025(3) O8 0.064(5) 0.060(4) 0.066(4) -0.010(3) -0.017(3) 0.034(3) O8A 0.15(2) 0.070(9) 0.150(16) 0.012(9) -0.058(15) 0.037(10) O9 0.156(7) 0.253(10) 0.159(6) -0.080(6) -0.060(6) 0.107(7) C1 0.0243(19) 0.040(2) 0.063(3) 0.0065(19) 0.0010(17) 0.0217(18) C2 0.028(2) 0.039(2) 0.057(2) 0.0031(19) 0.0010(17) 0.0202(19) C3 0.0230(17) 0.041(3) 0.035(3) -0.006(3) -0.0032(13) 0.0207(16) C4 0.0261(19) 0.036(2) 0.056(2) -0.0038(19) -0.0009(18) 0.0189(17) C5 0.0210(18) 0.040(2) 0.056(2) -0.0104(19) -0.0059(18) 0.0151(17) C6 0.0222(17) 0.048(3) 0.036(3) -0.005(3) -0.0025(13) 0.0241(16) C7 0.036(2) 0.036(2) 0.033(3) -0.002(2) -0.002(2) 0.019(3) C8 0.032(2) 0.048(3) 0.089(3) 0.025(3) 0.010(2) 0.022(2) C9 0.038(3) 0.038(3) 0.127(7) 0.017(4) 0.017(4) 0.021(3) C10 0.028(2) 0.028(2) 0.031(3) -0.0043(18) -0.0043(18) 0.010(2) C11 0.035(3) 0.042(3) 0.102(4) -0.029(3) -0.008(3) 0.017(2) C12 0.040(3) 0.040(3) 0.160(9) -0.031(4) -0.031(4) 0.026(4) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 O1 2.060(3) 5 ? Cu1 O1 2.060(3) . ? Cu1 O2 2.075(3) 5 ? Cu1 O2 2.075(3) . ? Cu1 N2 2.147(4) 1_655 ? Cu1 N1 2.156(4) . ? N1 C1 1.348(5) . ? N1 C1 1.348(5) 5 ? N2 C4 1.349(5) . ? N2 C4 1.350(5) 5 ? N2 Cu1 2.147(4) 1_455 ? N3 C7 1.352(5) . ? N3 C8 1.398(6) . ? N4 C10 1.367(5) . ? N4 C11 1.405(6) . ? O3 C7 1.248(7) . ? O4 C8 1.262(6) . ? O5 C10 1.233(6) . ? O6 C11 1.254(6) . ? O8 O8A 1.38(2) . ? C1 C2 1.388(6) . ? C2 C3 1.395(5) . ? C3 C2 1.394(5) 5 ? C3 C6 1.501(7) . ? C4 C5 1.398(5) . ? C5 C6 1.391(5) . ? C6 C5 1.391(5) 5 ? C7 N3 1.353(5) 3_665 ? C8 C9 1.389(6) . ? C9 C8 1.389(6) 3_665 ? C10 N4 1.368(5) 3_665 ? C11 C12 1.381(6) . ? C12 C11 1.380(6) 3_665 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 Cu1 O1 179.45(16) 5 . ? O1 Cu1 O2 89.53(12) 5 5 ? O1 Cu1 O2 90.49(12) . 5 ? O1 Cu1 O2 90.49(12) 5 . ? O1 Cu1 O2 89.53(12) . . ? O2 Cu1 O2 176.20(16) 5 . ? O1 Cu1 N2 89.74(8) 5 1_655 ? O1 Cu1 N2 89.71(8) . 1_655 ? O2 Cu1 N2 91.89(8) 5 1_655 ? O2 Cu1 N2 91.91(8) . 1_655 ? O1 Cu1 N1 90.26(8) 5 . ? O1 Cu1 N1 90.29(8) . . ? O2 Cu1 N1 88.11(8) 5 . ? O2 Cu1 N1 88.09(8) . . ? N2 Cu1 N1 180.0 1_655 . ? C1 N1 C1 116.4(5) . 5 ? C1 N1 Cu1 121.8(2) . . ? C1 N1 Cu1 121.8(2) 5 . ? C4 N2 C4 116.9(4) . 5 ? C4 N2 Cu1 121.5(2) . 1_455 ? C4 N2 Cu1 121.6(2) 5 1_455 ? C7 N3 C8 124.6(4) . . ? C10 N4 C11 124.9(4) . . ? N1 C1 C2 123.4(4) . . ? C1 C2 C3 120.4(4) . . ? C2 C3 C2 116.0(5) 5 . ? C2 C3 C6 122.0(2) 5 . ? C2 C3 C6 122.0(2) . . ? N2 C4 C5 123.2(4) . . ? C6 C5 C4 119.4(4) . . ? C5 C6 C5 117.8(5) 5 . ? C5 C6 C3 121.1(2) 5 . ? C5 C6 C3 121.1(2) . . ? O3 C7 N3 121.9(3) . . ? O3 C7 N3 121.9(3) . 3_665 ? N3 C7 N3 116.2(5) . 3_665 ? O4 C8 C9 126.5(5) . . ? O4 C8 N3 117.0(5) . . ? C9 C8 N3 116.4(5) . . ? C8 C9 C8 121.8(6) 3_665 . ? O5 C10 N4 122.7(2) . . ? O5 C10 N4 122.8(2) . 3_665 ? N4 C10 N4 114.5(5) . 3_665 ? O6 C11 C12 124.3(5) . . ? O6 C11 N4 118.5(5) . . ? C12 C11 N4 117.2(5) . . ? C11 C12 C11 121.3(6) 3_665 . ? 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 O1 Cu1 N1 C1 -12.6(2) . . . . no O1 Cu1 N1 C1 167.4(2) . . . 5_555 no O2 Cu1 N1 C1 -102.1(2) . . . . no O2 Cu1 N1 C1 77.9(2) . . . 5_555 no O1 Cu1 N1 C1 167.4(2) 5_555 . . . no O1 Cu1 N2 C4 137.2(2) . . . . no O1 Cu1 N2 C4 -42.8(2) . . . 5_555 no O2 Cu1 N2 C4 47.7(2) . . . . no O2 Cu1 N2 C4 -132.3(2) . . . 5_555 no O1 Cu1 N2 C4 -42.8(2) 5_555 . . . no Cu1 N1 C1 C2 -180.0(3) . . . . no C1 N1 C1 C2 0.0(5) 5_555 . . . no C8 N3 C7 N3 -1.8(5) . . . 3_665 no C7 N3 C8 O4 -177.0(4) . . . . no C7 N3 C8 C9 3.4(7) . . . . no C8 N3 C7 O3 178.2(3) . . . . no C10 N4 C11 C12 0.1(7) . . . . no C11 N4 C10 O5 180.0(4) . . . . no C11 N4 C10 N4 0.0(5) . . . 3_665 no C10 N4 C11 O6 -179.6(4) . . . . no N1 C1 C2 C3 0.0(6) . . . . no C1 C2 C3 C2 0.0(5) . . . 5_555 no C1 C2 C3 C6 -180.0(3) . . . 1_455 no O4 C8 C9 C8 179.0(5) . . . 3_665 no N3 C8 C9 C8 -1.6(6) . . . 3_665 no O6 C11 C12 C11 179.6(5) . . . 3_665 no N4 C11 C12 C11 0.0(6) . . . 3_665 no loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A _geom_hbond_publ_flag # #D H A D - H H...A D...A D - H...A symm(A) # O1 H1A O3 0.8600 1.9400 2.788(4) 172.00 3_655 yes O1 H1B O8 0.8200 1.9100 2.731(7) 175.00 1_445 yes O2 H2A O7 0.8400 1.9400 2.749(7) 162.00 . yes O2 H2B O5 0.8300 2.0000 2.816(4) 168.00 3_565 yes N3 H3N O6 0.8600 1.9600 2.795(7) 164.00 1_565 yes O7 H7A O6 0.7500 2.2700 3.020(8) 179.00 . yes O7 H7B O9 0.8400 2.5800 3.427(11) 178.00 . yes O8 H8B O4 0.7000 2.1200 2.819(10) 177.00 11_654 yes O9 H9A O8 0.8500 1.8700 2.715(15) 179.00 5_565 yes C1 H1 O1 0.9300 2.4600 3.038(6) 121.00 . yes