Electronic Supplementary Material for CrystEngComm This journal is (c) The Royal Society of Chemistry 2007 data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 _publ_contact_author_name 'Ezequiel M. Vazquez-Lopez' _publ_contact_author_address ; Departamento de Quimica Inorgancia Universidade de Vigo Facultade de Quimica Edificio de Ciencias Experimentais Vigo Galicia E-36310 SPAIN ; _publ_contact_author_email EZEQUIEL@UVIGO.ES _publ_section_title ; Synthesis and Structure of 2-acetylpyridine-salicyloylhydrazone and its Copper(II) and Zinc(II) Complexes. The effect of the metal coordination on the weak intermolecular interactions ; loop_ _publ_author_name 'Ezequiel M. Vazquez-Lopez' 'Paula Barbazan' 'Rosa Carballo' #=============================================================================== ############### # CCDC 639030 # ############### data_H2L _database_code_depnum_ccdc_archive 'CCDC 639030' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H13 N3 O2' _chemical_formula_weight 255.27 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' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pbca loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z-1/2' '-x-1/2, y-1/2, z' 'x, -y-1/2, z-1/2' _cell_length_a 12.8373(14) _cell_length_b 11.8355(13) _cell_length_c 16.975(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2579.1(5) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description irregular _exptl_crystal_colour colorless _exptl_crystal_size_max 0.43 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.19 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.315 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1072 _exptl_absorpt_coefficient_mu 0.091 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.498659 _exptl_absorpt_correction_T_max 1.000000 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type '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 12238 _diffrn_reflns_av_R_equivalents 0.1297 _diffrn_reflns_av_sigmaI/netI 0.2318 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 2.40 _diffrn_reflns_theta_max 28.06 _reflns_number_total 3032 _reflns_number_gt 841 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0449P)^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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3032 _refine_ls_number_parameters 172 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.2955 _refine_ls_R_factor_gt 0.0523 _refine_ls_wR_factor_ref 0.1452 _refine_ls_wR_factor_gt 0.0918 _refine_ls_goodness_of_fit_ref 0.799 _refine_ls_restrained_S_all 0.799 _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 O1 O 0.0195(2) 0.3149(2) 0.48689(16) 0.0976(10) Uani 1 1 d . . . O2 O 0.33137(16) 0.23553(19) 0.47681(12) 0.0605(7) Uani 1 1 d . . . H2 H 0.3912 0.2118 0.4804 0.073 Uiso 1 1 calc R . . N1 N 0.17036(19) 0.3504(2) 0.42795(16) 0.0508(8) Uani 1 1 d . . . H1 H 0.2353 0.3345 0.4226 0.061 Uiso 1 1 calc R . . N2 N 0.1274(2) 0.4392(2) 0.38604(16) 0.0493(8) Uani 1 1 d . . . N3 N 0.2082(2) 0.6628(3) 0.26408(17) 0.0564(8) Uani 1 1 d . . . C1 C 0.1109(3) 0.2892(3) 0.4768(2) 0.0546(10) Uani 1 1 d . . . C2 C 0.1596(3) 0.1915(3) 0.51762(19) 0.0467(9) Uani 1 1 d . . . C3 C 0.2657(3) 0.1651(3) 0.51658(19) 0.0440(9) Uani 1 1 d . . . C4 C 0.3027(3) 0.0707(3) 0.55475(19) 0.0508(10) Uani 1 1 d . . . H4 H 0.3735 0.0542 0.5538 0.061 Uiso 1 1 calc R . . C5 C 0.2353(3) 0.0010(3) 0.5942(2) 0.0671(11) Uani 1 1 d . . . H5 H 0.2606 -0.0633 0.6193 0.081 Uiso 1 1 calc R . . C6 C 0.1310(3) 0.0251(3) 0.5971(2) 0.0774(13) Uani 1 1 d . . . H6 H 0.0856 -0.0218 0.6244 0.093 Uiso 1 1 calc R . . C7 C 0.0945(3) 0.1194(3) 0.5591(2) 0.0704(12) Uani 1 1 d . . . H7 H 0.0237 0.1354 0.5612 0.084 Uiso 1 1 calc R . . C8 C 0.1924(3) 0.5040(3) 0.34980(19) 0.0430(9) Uani 1 1 d . . . C9 C 0.1439(3) 0.5971(3) 0.30481(19) 0.0442(9) Uani 1 1 d . . . C13 C 0.1666(4) 0.7462(3) 0.2214(2) 0.0704(12) Uani 1 1 d . . . H13 H 0.2113 0.7924 0.1928 0.084 Uiso 1 1 calc R . . C10 C 0.0371(3) 0.6150(3) 0.3048(2) 0.0627(11) Uani 1 1 d . . . H10 H -0.0062 0.5691 0.3349 0.075 Uiso 1 1 calc R . . C11 C -0.0049(3) 0.7014(4) 0.2601(2) 0.0729(12) Uani 1 1 d . . . H11 H -0.0763 0.7144 0.2590 0.087 Uiso 1 1 calc R . . C12 C 0.0624(4) 0.7674(3) 0.2172(2) 0.0741(13) Uani 1 1 d . . . H12 H 0.0373 0.8257 0.1858 0.089 Uiso 1 1 calc R . . C14 C 0.3086(3) 0.4934(3) 0.3520(2) 0.0654(11) Uani 1 1 d . . . H14A H 0.3296 0.4622 0.4017 0.098 Uiso 1 1 calc R . . H14B H 0.3396 0.5666 0.3453 0.098 Uiso 1 1 calc R . . H14C H 0.3312 0.4444 0.3102 0.098 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 O1 0.0400(16) 0.109(2) 0.144(3) 0.0630(19) 0.0274(17) 0.0124(14) O2 0.0356(13) 0.0666(18) 0.0795(17) 0.0241(15) 0.0008(12) 0.0003(13) N1 0.0319(16) 0.0543(19) 0.066(2) 0.0094(17) 0.0057(16) -0.0002(16) N2 0.0461(19) 0.0489(19) 0.0528(19) 0.0063(16) -0.0051(16) 0.0040(16) N3 0.063(2) 0.051(2) 0.055(2) 0.0084(18) 0.0035(17) -0.0014(18) C1 0.036(2) 0.062(3) 0.067(3) 0.006(2) 0.007(2) -0.009(2) C2 0.042(2) 0.044(2) 0.054(2) 0.0097(19) 0.0018(19) -0.0007(19) C3 0.046(2) 0.043(2) 0.043(2) 0.004(2) -0.0001(19) -0.0022(19) C4 0.050(2) 0.048(2) 0.054(2) 0.003(2) -0.006(2) 0.003(2) C5 0.075(3) 0.053(3) 0.074(3) 0.013(2) 0.004(3) 0.001(2) C6 0.068(3) 0.074(3) 0.091(3) 0.035(3) 0.022(3) -0.006(2) C7 0.052(3) 0.071(3) 0.088(3) 0.024(3) 0.018(2) -0.004(2) C8 0.040(2) 0.047(2) 0.042(2) -0.0028(19) 0.0014(18) -0.003(2) C9 0.050(2) 0.046(2) 0.036(2) -0.0028(19) -0.0030(18) 0.004(2) C13 0.087(3) 0.058(3) 0.066(3) 0.014(2) 0.001(2) 0.002(3) C10 0.054(3) 0.063(3) 0.071(3) 0.004(2) -0.002(2) 0.006(2) C11 0.060(3) 0.077(3) 0.081(3) 0.004(3) -0.018(2) 0.014(3) C12 0.088(3) 0.061(3) 0.074(3) 0.007(2) -0.021(3) 0.010(3) C14 0.051(3) 0.070(3) 0.075(3) 0.011(2) 0.006(2) 0.001(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C1 1.225(3) . ? O2 C3 1.364(3) . ? N1 C1 1.339(4) . ? N1 N2 1.384(3) . ? N2 C8 1.290(4) . ? N3 C9 1.329(4) . ? N3 C13 1.336(4) . ? C1 C2 1.485(4) . ? C2 C7 1.387(4) . ? C2 C3 1.397(4) . ? C3 C4 1.376(4) . ? C4 C5 1.370(4) . ? C5 C6 1.369(4) . ? C6 C7 1.371(4) . ? C8 C9 1.478(4) . ? C8 C14 1.497(4) . ? C9 C10 1.388(4) . ? C13 C12 1.362(5) . ? C10 C11 1.382(4) . ? C11 C12 1.373(5) . ? 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 N1 N2 120.1(3) . . ? C8 N2 N1 116.0(3) . . ? C9 N3 C13 117.8(3) . . ? O1 C1 N1 119.9(3) . . ? O1 C1 C2 122.1(3) . . ? N1 C1 C2 118.0(3) . . ? C7 C2 C3 117.1(3) . . ? C7 C2 C1 117.6(3) . . ? C3 C2 C1 125.3(3) . . ? O2 C3 C4 121.0(3) . . ? O2 C3 C2 118.1(3) . . ? C4 C3 C2 120.8(3) . . ? C5 C4 C3 120.1(3) . . ? C4 C5 C6 120.6(4) . . ? C7 C6 C5 119.2(4) . . ? C6 C7 C2 122.3(4) . . ? N2 C8 C9 114.6(3) . . ? N2 C8 C14 125.6(3) . . ? C9 C8 C14 119.7(3) . . ? N3 C9 C10 121.6(3) . . ? N3 C9 C8 116.3(3) . . ? C10 C9 C8 122.1(4) . . ? N3 C13 C12 123.9(4) . . ? C11 C10 C9 119.8(4) . . ? C12 C11 C10 117.8(4) . . ? C13 C12 C11 119.0(4) . . ? 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 N1 H1 O2 0.86 1.93 2.609(3) 134.5 . O2 H2 O1 0.82 1.77 2.563(3) 163.2 3_556 _diffrn_measured_fraction_theta_max 0.967 _diffrn_reflns_theta_full 28.06 _diffrn_measured_fraction_theta_full 0.967 _refine_diff_density_max 0.154 _refine_diff_density_min -0.172 _refine_diff_density_rms 0.041 ############### # CCDC 639031 # ############### data_[CuBr(HL)] _database_code_depnum_ccdc_archive 'CCDC 639031' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H12 Br Cu N3 O2' _chemical_formula_weight 397.72 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' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 6.7539(9) _cell_length_b 9.3441(12) _cell_length_c 11.4902(15) _cell_angle_alpha 89.773(3) _cell_angle_beta 81.497(3) _cell_angle_gamma 88.363(3) _cell_volume 716.87(16) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prism _exptl_crystal_colour brown _exptl_crystal_size_max 0.21 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.843 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 394 _exptl_absorpt_coefficient_mu 4.317 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.627515 _exptl_absorpt_correction_T_max 1.000000 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type '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 4816 _diffrn_reflns_av_R_equivalents 0.0849 _diffrn_reflns_av_sigmaI/netI 0.1634 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.79 _diffrn_reflns_theta_max 28.07 _reflns_number_total 3320 _reflns_number_gt 1441 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0338P)^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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3320 _refine_ls_number_parameters 191 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1337 _refine_ls_R_factor_gt 0.0491 _refine_ls_wR_factor_ref 0.1028 _refine_ls_wR_factor_gt 0.0835 _refine_ls_goodness_of_fit_ref 0.752 _refine_ls_restrained_S_all 0.752 _refine_ls_shift/su_max 0.025 _refine_ls_shift/su_mean 0.001 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 Cu Cu 0.20682(11) 0.09714(6) 0.12189(6) 0.0420(2) Uani 1 1 d . . . Br Br 0.15097(12) 0.28208(6) 0.25726(6) 0.0717(3) Uani 1 1 d . . . O1 O 0.2373(6) 0.2115(3) -0.0212(3) 0.0481(10) Uani 1 1 d . . . C2 C 0.2949(8) 0.2048(6) -0.2296(5) 0.0398(14) Uani 1 1 d . . . N3 N 0.1948(6) -0.0723(4) 0.2267(4) 0.0368(11) Uani 1 1 d . . . N1 N 0.2785(6) -0.0093(4) -0.1110(4) 0.0444(12) Uani 1 1 d . . . C8 C 0.2525(8) -0.1827(5) 0.0381(5) 0.0427(14) Uani 1 1 d . . . N2 N 0.2512(6) -0.0513(4) 0.0041(4) 0.0389(11) Uani 1 1 d . . . C9 C 0.2193(7) -0.1991(5) 0.1663(5) 0.0378(13) Uani 1 1 d . . . C1 C 0.2670(8) 0.1350(6) -0.1138(5) 0.0414(14) Uani 1 1 d . . . O2 O 0.3390(6) -0.0151(4) -0.3409(3) 0.0607(12) Uani 1 1 d . . . H2 H 0.3198 -0.0472 -0.2738 0.073 Uiso 1 1 calc R . . C3 C 0.3323(8) 0.1273(6) -0.3369(5) 0.0424(14) Uani 1 1 d . . . C4 C 0.3593(8) 0.2013(7) -0.4422(5) 0.0489(15) Uani 1 1 d . . . H4 H 0.3872 0.1511 -0.5127 0.059 Uiso 1 1 calc R . . C6 C 0.3078(9) 0.4245(6) -0.3396(6) 0.0551(17) Uani 1 1 d . . . H6 H 0.2990 0.5240 -0.3412 0.066 Uiso 1 1 calc R . . C13 C 0.1634(8) -0.0768(6) 0.3426(5) 0.0445(14) Uani 1 1 d . . . H13 H 0.1469 0.0093 0.3836 0.053 Uiso 1 1 calc R . . C12 C 0.1540(9) -0.2025(7) 0.4063(6) 0.0567(17) Uani 1 1 d . . . H12 H 0.1328 -0.2013 0.4881 0.068 Uiso 1 1 calc R . . C7 C 0.2842(8) 0.3530(6) -0.2358(5) 0.0460(15) Uani 1 1 d . . . H7 H 0.2600 0.4053 -0.1662 0.055 Uiso 1 1 calc R . . C10 C 0.2123(8) -0.3269(6) 0.2261(6) 0.0517(16) Uani 1 1 d . . . H10 H 0.2319 -0.4127 0.1846 0.062 Uiso 1 1 calc R . . C5 C 0.3456(9) 0.3460(7) -0.4436(5) 0.0554(16) Uani 1 1 d . . . H5 H 0.3617 0.3939 -0.5153 0.066 Uiso 1 1 calc R . . C11 C 0.1765(9) -0.3285(6) 0.3461(6) 0.0531(17) Uani 1 1 d . . . H11 H 0.1676 -0.4150 0.3865 0.064 Uiso 1 1 calc R . . C14 C 0.2862(9) -0.3068(5) -0.0451(5) 0.0611(18) Uani 1 1 d . . . H14A H 0.1594 -0.3438 -0.0568 0.092 Uiso 1 1 calc R . . H14B H 0.3639 -0.3804 -0.0128 0.092 Uiso 1 1 calc R . . H14C H 0.3568 -0.2758 -0.1192 0.092 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 Cu 0.0548(5) 0.0327(4) 0.0382(5) 0.0008(3) -0.0056(4) -0.0028(3) Br 0.1304(8) 0.0388(4) 0.0446(4) -0.0049(3) -0.0086(4) -0.0009(4) O1 0.071(3) 0.034(2) 0.039(2) -0.0004(17) -0.004(2) -0.001(2) C2 0.029(3) 0.049(3) 0.041(4) 0.005(3) -0.003(3) -0.003(3) N3 0.034(3) 0.038(2) 0.039(3) 0.009(2) -0.005(2) -0.007(2) N1 0.046(3) 0.042(3) 0.046(3) -0.001(2) -0.009(2) -0.001(2) C8 0.034(4) 0.037(3) 0.057(4) 0.002(3) -0.006(3) 0.000(3) N2 0.047(3) 0.033(2) 0.038(3) 0.002(2) -0.009(2) -0.009(2) C9 0.029(3) 0.033(3) 0.052(4) 0.008(3) -0.008(3) 0.001(3) C1 0.038(4) 0.044(3) 0.042(4) 0.004(3) -0.006(3) 0.003(3) O2 0.079(3) 0.054(3) 0.046(3) -0.003(2) 0.002(2) -0.005(2) C3 0.030(3) 0.050(4) 0.046(4) 0.000(3) -0.004(3) -0.003(3) C4 0.032(4) 0.078(4) 0.035(4) 0.000(3) 0.002(3) -0.003(3) C6 0.050(4) 0.052(4) 0.064(5) 0.018(3) -0.009(4) -0.005(3) C13 0.040(4) 0.052(4) 0.042(4) 0.003(3) -0.006(3) -0.004(3) C12 0.051(4) 0.068(4) 0.051(4) 0.024(3) -0.008(3) -0.002(4) C7 0.044(4) 0.047(3) 0.045(4) 0.005(3) -0.002(3) -0.004(3) C10 0.046(4) 0.037(3) 0.073(5) 0.007(3) -0.012(4) 0.000(3) C5 0.041(4) 0.081(5) 0.043(4) 0.022(3) -0.002(3) -0.004(4) C11 0.043(4) 0.044(4) 0.072(5) 0.025(3) -0.009(3) -0.006(3) C14 0.075(5) 0.040(3) 0.067(5) -0.009(3) -0.010(4) 0.005(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 Cu N2 1.928(4) . ? Cu O1 1.946(3) . ? Cu N3 1.982(4) . ? Cu Br 2.3149(9) . ? O1 C1 1.271(6) . ? C2 C7 1.387(7) . ? C2 C3 1.419(7) . ? C2 C1 1.468(7) . ? N3 C13 1.318(6) . ? N3 C9 1.369(6) . ? N1 C1 1.349(6) . ? N1 N2 1.366(6) . ? C8 N2 1.287(6) . ? C8 C9 1.465(7) . ? C8 C14 1.497(7) . ? C9 C10 1.374(7) . ? O2 C3 1.331(6) . ? C3 C4 1.382(7) . ? C4 C5 1.353(7) . ? C6 C7 1.356(7) . ? C6 C5 1.392(8) . ? C13 C12 1.379(7) . ? C12 C11 1.361(8) . ? C10 C11 1.364(8) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N2 Cu O1 79.32(16) . . ? N2 Cu N3 80.92(18) . . ? O1 Cu N3 160.23(17) . . ? N2 Cu Br 177.61(13) . . ? O1 Cu Br 98.36(10) . . ? N3 Cu Br 101.40(13) . . ? C1 O1 Cu 112.5(3) . . ? C7 C2 C3 117.8(5) . . ? C7 C2 C1 119.3(5) . . ? C3 C2 C1 122.9(5) . . ? C13 N3 C9 118.3(5) . . ? C13 N3 Cu 128.8(4) . . ? C9 N3 Cu 113.0(4) . . ? C1 N1 N2 108.0(4) . . ? N2 C8 C9 113.5(5) . . ? N2 C8 C14 123.4(5) . . ? C9 C8 C14 123.2(5) . . ? C8 N2 N1 124.2(4) . . ? C8 N2 Cu 118.6(4) . . ? N1 N2 Cu 117.3(3) . . ? N3 C9 C10 120.3(5) . . ? N3 C9 C8 114.1(4) . . ? C10 C9 C8 125.6(5) . . ? O1 C1 N1 122.9(5) . . ? O1 C1 C2 119.5(5) . . ? N1 C1 C2 117.7(5) . . ? O2 C3 C4 118.0(5) . . ? O2 C3 C2 122.7(5) . . ? C4 C3 C2 119.3(5) . . ? C5 C4 C3 120.6(6) . . ? C7 C6 C5 118.6(6) . . ? N3 C13 C12 123.5(5) . . ? C11 C12 C13 118.2(6) . . ? C6 C7 C2 122.4(6) . . ? C11 C10 C9 120.2(5) . . ? C4 C5 C6 121.2(6) . . ? C10 C11 C12 119.6(5) . . ? 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 O2 H2 N1 0.82 1.88 2.613(6) 147.6 . C4 H4 O2 0.93 2.61 3.423(7) 146.0 2_654 C10 H10 Br 0.93 3.01 3.698(5) 132.0 1_545 _diffrn_measured_fraction_theta_max 0.953 _diffrn_reflns_theta_full 28.07 _diffrn_measured_fraction_theta_full 0.953 _refine_diff_density_max 0.493 _refine_diff_density_min -0.575 _refine_diff_density_rms 0.102 ############### # CCDC 639032 # ############### data_[Zn(HL)2] _database_code_depnum_ccdc_archive 'CCDC 639032' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C28 H24 N6 O4 Zn' _chemical_formula_weight 573.90 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 Orthorhombic _symmetry_space_group_name_H-M Aba2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z' '-x+1/2, y, z+1/2' 'x+1/2, -y, z+1/2' 'x, y+1/2, z+1/2' '-x, -y+1/2, z+1/2' '-x+1/2, y+1/2, z+1' 'x+1/2, -y+1/2, z+1' _cell_length_a 12.598(4) _cell_length_b 18.483(6) _cell_length_c 10.818(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2518.9(15) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prism _exptl_crystal_colour orange _exptl_crystal_size_max 0.29 _exptl_crystal_size_mid 0.19 _exptl_crystal_size_min 0.19 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.513 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1184 _exptl_absorpt_coefficient_mu 1.023 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.780641 _exptl_absorpt_correction_T_max 1.000000 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type '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 8039 _diffrn_reflns_av_R_equivalents 0.0721 _diffrn_reflns_av_sigmaI/netI 0.1056 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.20 _diffrn_reflns_theta_max 28.01 _reflns_number_total 2948 _reflns_number_gt 1533 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0187P)^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 constr _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 0.068(18) _refine_ls_number_reflns 2948 _refine_ls_number_parameters 178 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.1166 _refine_ls_R_factor_gt 0.0512 _refine_ls_wR_factor_ref 0.0788 _refine_ls_wR_factor_gt 0.0691 _refine_ls_goodness_of_fit_ref 0.889 _refine_ls_restrained_S_all 0.888 _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 Zn Zn 0.0000 0.0000 0.27776(8) 0.05165(19) Uani 1 2 d S . . O1 O -0.0093(2) 0.08675(16) 0.4089(3) 0.0610(8) Uani 1 1 d . . . O2 O 0.2863(3) 0.1637(2) 0.5313(4) 0.0944(13) Uani 1 1 d . . . H2 H 0.2732 0.1374 0.4723 0.113 Uiso 1 1 calc R . . N1 N 0.1731(3) 0.08986(18) 0.3845(3) 0.0511(10) Uani 1 1 d . . . N2 N 0.1540(2) 0.03989(19) 0.2936(5) 0.0522(10) Uani 1 1 d . . . N3 N 0.0883(3) -0.0571(2) 0.1364(3) 0.0510(10) Uani 1 1 d . . . C1 C 0.0818(3) 0.1108(2) 0.4372(4) 0.0467(11) Uani 1 1 d . . . C2 C 0.0941(3) 0.1659(2) 0.5371(4) 0.0499(12) Uani 1 1 d . . . C3 C 0.1943(4) 0.1869(3) 0.5823(5) 0.0670(15) Uani 1 1 d . . . C4 C 0.1991(4) 0.2334(3) 0.6842(5) 0.0858(18) Uani 1 1 d . . . H4 H 0.2648 0.2473 0.7155 0.103 Uiso 1 1 calc R . . C5 C 0.1098(4) 0.2583(3) 0.7373(5) 0.0835(19) Uani 1 1 d . . . H5 H 0.1147 0.2886 0.8057 0.100 Uiso 1 1 calc R . . C6 C 0.0112(5) 0.2399(3) 0.6926(5) 0.0782(15) Uani 1 1 d . . . H6 H -0.0498 0.2588 0.7288 0.094 Uiso 1 1 calc R . . C7 C 0.0038(4) 0.1935(2) 0.5944(4) 0.0652(12) Uani 1 1 d . . . H7 H -0.0629 0.1802 0.5654 0.078 Uiso 1 1 calc R . . C8 C 0.2289(3) 0.0109(2) 0.2300(4) 0.0562(13) Uani 1 1 d . . . C9 C 0.1934(4) -0.0402(3) 0.1348(4) 0.0542(12) Uani 1 1 d . . . C10 C 0.2618(5) -0.0698(2) 0.0480(6) 0.0728(17) Uani 1 1 d . . . H10 H 0.3341 -0.0596 0.0493 0.087 Uiso 1 1 calc R . . C11 C 0.2188(4) -0.1146(3) -0.0400(5) 0.0760(16) Uani 1 1 d . . . H11 H 0.2627 -0.1334 -0.1013 0.091 Uiso 1 1 calc R . . C12 C 0.1122(5) -0.1326(3) -0.0404(5) 0.0809(17) Uani 1 1 d . . . H12 H 0.0833 -0.1638 -0.0988 0.097 Uiso 1 1 calc R . . C13 C 0.0507(4) -0.1009(3) 0.0525(5) 0.0749(16) Uani 1 1 d . . . H13 H -0.0214 -0.1117 0.0547 0.090 Uiso 1 1 d R . . C14 C 0.3455(3) 0.0285(2) 0.2504(6) 0.0768(19) Uani 1 1 d . . . H14A H 0.3735 -0.0019 0.3146 0.115 Uiso 1 1 d R . . H14B H 0.3842 0.0202 0.1752 0.115 Uiso 1 1 d R . . H14C H 0.3526 0.0783 0.2742 0.115 Uiso 1 1 d 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 Zn 0.0302(3) 0.0744(4) 0.0504(3) 0.000 0.000 -0.0019(4) O1 0.0317(17) 0.087(2) 0.065(2) -0.0112(17) 0.0001(18) -0.0146(16) O2 0.047(3) 0.108(3) 0.128(3) -0.028(3) -0.014(3) -0.006(2) N1 0.047(2) 0.047(2) 0.059(3) -0.004(2) -0.0004(19) -0.0022(18) N2 0.0348(19) 0.064(2) 0.058(3) 0.016(3) 0.002(2) 0.0033(16) N3 0.046(3) 0.053(2) 0.054(3) 0.009(2) 0.008(2) 0.006(2) C1 0.044(3) 0.050(3) 0.047(3) 0.009(2) -0.003(2) -0.005(2) C2 0.040(3) 0.058(3) 0.053(3) 0.005(3) -0.007(2) -0.012(2) C3 0.051(3) 0.069(4) 0.082(4) -0.005(3) -0.011(3) 0.000(3) C4 0.055(4) 0.106(5) 0.096(5) -0.023(4) -0.024(3) -0.013(3) C5 0.089(4) 0.075(4) 0.087(5) -0.021(3) -0.010(3) -0.020(3) C6 0.057(3) 0.096(4) 0.082(3) -0.022(3) -0.001(3) -0.016(3) C7 0.045(3) 0.079(3) 0.072(3) -0.011(3) -0.003(3) -0.016(3) C8 0.036(2) 0.062(3) 0.070(4) 0.012(3) 0.008(2) -0.002(2) C9 0.048(3) 0.053(3) 0.061(3) 0.013(3) 0.008(3) 0.010(2) C10 0.071(4) 0.064(3) 0.084(5) 0.014(4) 0.021(4) 0.028(3) C11 0.086(4) 0.066(4) 0.075(4) 0.010(3) 0.028(4) 0.029(3) C12 0.099(5) 0.073(4) 0.070(4) -0.014(3) 0.007(4) 0.024(4) C13 0.068(4) 0.085(4) 0.071(4) 0.006(4) -0.005(3) 0.005(3) C14 0.031(2) 0.081(3) 0.119(6) 0.018(3) 0.003(3) 0.0021(19) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Zn N2 2.082(3) . ? Zn N2 2.082(3) 2 ? Zn O1 2.144(3) . ? Zn O1 2.144(3) 2 ? Zn N3 2.166(4) . ? Zn N3 2.166(4) 2 ? O1 C1 1.268(4) . ? O2 C3 1.353(5) . ? N1 C1 1.341(5) . ? N1 N2 1.371(5) . ? N2 C8 1.286(5) . ? N3 C13 1.306(6) . ? N3 C9 1.360(5) . ? C1 C2 1.493(6) . ? C2 C7 1.393(6) . ? C2 C3 1.408(6) . ? C3 C4 1.400(7) . ? C4 C5 1.345(6) . ? C5 C6 1.375(7) . ? C6 C7 1.368(6) . ? C8 C9 1.467(6) . ? C8 C14 1.521(5) . ? C9 C10 1.387(6) . ? C10 C11 1.373(7) . ? C11 C12 1.384(7) . ? C12 C13 1.397(7) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N2 Zn N2 170.6(3) . 2 ? N2 Zn O1 74.44(15) . . ? N2 Zn O1 99.18(14) 2 . ? N2 Zn O1 99.17(14) . 2 ? N2 Zn O1 74.44(15) 2 2 ? O1 Zn O1 97.15(16) . 2 ? N2 Zn N3 75.64(18) . . ? N2 Zn N3 111.36(16) 2 . ? O1 Zn N3 149.28(12) . . ? O1 Zn N3 94.29(12) 2 . ? N2 Zn N3 111.36(16) . 2 ? N2 Zn N3 75.64(18) 2 2 ? O1 Zn N3 94.29(12) . 2 ? O1 Zn N3 149.28(12) 2 2 ? N3 Zn N3 90.2(2) . 2 ? C1 O1 Zn 111.8(3) . . ? C1 N1 N2 110.4(4) . . ? C8 N2 N1 122.4(4) . . ? C8 N2 Zn 119.5(3) . . ? N1 N2 Zn 117.5(3) . . ? C13 N3 C9 119.1(4) . . ? C13 N3 Zn 127.4(4) . . ? C9 N3 Zn 113.4(3) . . ? O1 C1 N1 124.9(4) . . ? O1 C1 C2 120.5(4) . . ? N1 C1 C2 114.6(4) . . ? C7 C2 C3 118.5(5) . . ? C7 C2 C1 119.2(4) . . ? C3 C2 C1 122.2(4) . . ? O2 C3 C4 118.5(5) . . ? O2 C3 C2 122.6(5) . . ? C4 C3 C2 118.8(5) . . ? C5 C4 C3 120.6(5) . . ? C4 C5 C6 121.5(6) . . ? C7 C6 C5 119.3(6) . . ? C6 C7 C2 121.3(5) . . ? N2 C8 C9 114.9(4) . . ? N2 C8 C14 122.9(4) . . ? C9 C8 C14 122.3(4) . . ? N3 C9 C10 121.5(5) . . ? N3 C9 C8 115.8(4) . . ? C10 C9 C8 122.7(5) . . ? C11 C10 C9 117.5(6) . . ? C10 C11 C12 122.0(5) . . ? C11 C12 C13 115.8(5) . . ? N3 C13 C12 124.0(5) . . ? 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 O2 H2 N1 0.82 1.81 2.533(5) 147.0 . C10 H10 O1 0.93 2.54 3.267(7) 135.4 4_554 _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 28.01 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.490 _refine_diff_density_min -0.280 _refine_diff_density_rms 0.046