#------------------------------------------------------------------------------ #$Date: 2020-02-17 11:24:03 +0200 (Mon, 17 Feb 2020) $ #$Revision: 248228 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/55/73/1557324.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/ # # All data on this site have been placed in the public domain by the # contributors. # data_1557324 loop_ _publ_author_name 'Loukiala, Satumari' 'Ratilainen, Jari' 'Valkonen, Jussi' 'Rissanen, Kari' _publ_section_title ; Syntheses and Crystal Structures of N,N'-Bis(2-hydroxybenzyl)piperazine, its Nitrate Salt and Copper(II) Acetate Complex. ; _journal_name_full 'Acta Chemica Scandinavica' _journal_page_first 1162 _journal_page_last 1168 _journal_paper_doi 10.3891/acta.chem.scand.51-1162 _journal_volume 51 _journal_year 1997 _chemical_formula_sum 'C18 H24 N4 O8' _chemical_formula_weight 424.41 _chemical_name_common ; N,N'-bis(2-hydroxybenzyl)piperazine nitrate ; _space_group_IT_number 61 _space_group_name_Hall '-P 2ac 2ab' _space_group_name_H-M_alt 'P b c a' _symmetry_cell_setting orthorhombic _symmetry_Int_Tables_number 61 _symmetry_space_group_name_Hall '-P 2ac 2ab' _symmetry_space_group_name_H-M 'P b c a' _cell_angle_alpha 90. _cell_angle_beta 90. _cell_angle_gamma 90. _cell_formula_units_Z 4 _cell_length_a 9.733(4) _cell_length_b 23.332(4) _cell_length_c 8.963(1) _cell_volume 2035.4(9) _diffrn_ambient_temperature 293 _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _exptl_absorpt_coefficient_mu 0.110 _exptl_crystal_density_diffrn 1.385 _exptl_crystal_F_000 896 _refine_ls_goodness_of_fit_ref 0.985 _refine_ls_number_parameters 142 _refine_ls_number_reflns 645 _refine_ls_R_factor_all 0.1393 _refine_ls_R_factor_gt 0.0491 _refine_ls_wR_factor_gt 0.0963 _refine_ls_wR_factor_ref 0.2245 _cod_data_source_file Acta-Chem-Scand-1997-51-1162-2.cif _cod_data_source_block 2 _cod_database_code 1557324 loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 x,y,z 2 1/2-x,-y,1/2+z 3 1/2+x,1/2-y,-z 4 -x,1/2+y,1/2-z 5 -x,-y,-z 6 1/2+x,y,1/2-z 7 1/2-x,1/2+y,z 8 x,1/2-y,1/2+z loop_ _atom_site_label _atom_site_type_symbol _atom_site_thermal_displace_type _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_occupancy _atom_site_U_iso_or_equiv _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O Uiso 0.8471(3) 0.38640(10) 0.5530(3) 1.000 0.0540(10) . . . . N1 N Uiso 0.5098(3) 0.44000(10) 0.5405(3) 1.000 0.0320(10) . . . . C1 C Uiso 0.6126(4) 0.4676(2) 0.4395(4) 1.000 0.0370(10) . . . . C2 C Uiso 0.4515(4) 0.4833(2) 0.6444(4) 1.000 0.0370(10) . . . . C3 C Uiso 0.5685(4) 0.3895(2) 0.6256(5) 1.000 0.0420(10) . . . . C4 C Uiso 0.6269(4) 0.3452(2) 0.5238(5) 1.000 0.0370(10) . . . . C5 C Uiso 0.7665(4) 0.3449(2) 0.4882(5) 1.000 0.0390(10) . . . . C6 C Uiso 0.8195(4) 0.3050(2) 0.3909(5) 1.000 0.0500(10) . . . . C7 C Uiso 0.7355(5) 0.2636(2) 0.3318(5) 1.000 0.062(2) . . . . C8 C Uiso 0.5984(5) 0.2621(2) 0.3683(5) 1.000 0.0600(10) . . . . C9 C Uiso 0.5445(4) 0.3027(2) 0.4634(5) 1.000 0.0510(10) . . . . O21 O Uiso 0.2872(3) 0.42200(10) 0.3479(3) 1.000 0.0570(10) . . . . O22 O Uiso 0.2151(3) 0.3909(2) 0.5566(4) 1.000 0.0930(10) . . . . O23 O Uiso 0.0723(3) 0.4058(2) 0.3802(4) 1.000 0.0840(10) . . . . N2 N Uiso 0.1908(4) 0.4062(2) 0.4297(5) 1.000 0.0530(10) . . . . H1 H Uiso 0.915(5) 0.386(2) 0.502(6) 1.000 0.0810 . . . . H2 H Uiso 0.435(3) 0.4247(14) 0.478(3) 1.000 0.0380 . . . . 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' 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 N1 C2 110.0(3) . . . yes C1 N1 C3 112.8(3) . . . yes C2 N1 C3 110.9(3) . . . yes C5 O1 H1 103(4) . . . no C3 N1 H2 106.4(19) . . . no C2 N1 H2 108.7(18) . . . no N1 C1 C2 110.7(3) . . 5_666 yes C1 N1 H2 107.8(17) . . . no N1 C2 C1 111.3(3) . . 5_666 yes N1 C3 C4 112.0(3) . . . yes C3 C4 C9 121.0(4) . . . no C5 C4 C9 118.1(4) . . . no C3 C4 C5 121.0(4) . . . no O1 C5 C4 117.1(4) . . . yes O1 C5 C6 122.0(4) . . . yes C4 C5 C6 120.9(4) . . . no C5 C6 C7 119.9(4) . . . no C6 C7 C8 120.3(4) . . . no C7 C8 C9 120.0(4) . . . no C4 C9 C8 120.9(4) . . . no O21 N2 O22 119.4(4) . . . yes O21 N2 O23 119.6(4) . . . yes O22 N2 O23 121.0(4) . . . yes loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C5 1.375(5) . . yes N1 C1 1.495(5) . . yes N1 C2 1.487(5) . . yes N1 C3 1.515(5) . . yes O1 H1 0.80(5) . . no C1 C2 1.506(6) . 5_666 no N1 H2 0.99(3) . . no C3 C4 1.491(6) . . no C4 C9 1.386(6) . . no C4 C5 1.396(6) . . no C5 C6 1.376(6) . . no C6 C7 1.372(6) . . no C7 C8 1.374(7) . . no C8 C9 1.378(6) . . no O21 N2 1.247(5) . . yes O22 N2 1.215(6) . . yes O23 N2 1.236(5) . . yes 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 O1 H1 O23 0.80(5) 1.94(5) 2.722(4) 166(5) 1_655 yes N1 H2 O21 0.99(3) 1.85(3) 2.802(4) 161(3) . yes N1 H2 O22 0.99(3) 2.39(3) 3.092(4) 128(2) . yes 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 C2 N1 C1 C2 -56.7(4) . . . 5_666 no C3 N1 C1 C2 178.9(3) . . . 5_666 no C1 N1 C2 C1 57.0(4) . . . 5_666 no C3 N1 C2 C1 -177.5(3) . . . 5_666 no C1 N1 C3 C4 -56.5(4) . . . . no C2 N1 C3 C4 179.6(3) . . . . no N1 C1 C2 N1 57.4(4) . . 5_666 5_666 no N1 C3 C4 C5 94.6(5) . . . . no N1 C3 C4 C9 -86.3(5) . . . . no C3 C4 C5 O1 1.1(6) . . . . no C3 C4 C5 C6 -178.1(4) . . . . no C9 C4 C5 O1 -178.1(4) . . . . no C9 C4 C5 C6 2.7(7) . . . . no C3 C4 C9 C8 179.4(4) . . . . no C5 C4 C9 C8 -1.4(7) . . . . no O1 C5 C6 C7 178.5(4) . . . . no C4 C5 C6 C7 -2.3(7) . . . . no C5 C6 C7 C8 0.6(7) . . . . no C6 C7 C8 C9 0.7(7) . . . . no C7 C8 C9 C4 -0.3(7) . . . . no