#------------------------------------------------------------------------------ #$Date: 2020-02-17 11:23:50 +0200 (Mon, 17 Feb 2020) $ #$Revision: 248227 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/55/73/1557323.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_1557323 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 H22 N2 O2' _chemical_formula_weight 298.38 _chemical_name_common ; N,N'-bis(2-hydroxybenzyl)piperazine ; _space_group_IT_number 14 _space_group_name_Hall '-P 2ybc' _space_group_name_H-M_alt 'P 1 21/c 1' _symmetry_cell_setting monoclinic _symmetry_Int_Tables_number 14 _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_space_group_name_H-M 'P 1 21/c 1' _cell_angle_alpha 90. _cell_angle_beta 98.99(3) _cell_angle_gamma 90. _cell_formula_units_Z 2 _cell_length_a 6.745(6) _cell_length_b 8.796(2) _cell_length_c 13.407(2) _cell_volume 785.7(7) _diffrn_ambient_temperature 293 _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _exptl_absorpt_coefficient_mu 0.083 _exptl_crystal_density_diffrn 1.261 _exptl_crystal_F_000 320 _refine_ls_goodness_of_fit_ref 0.979 _refine_ls_number_parameters 103 _refine_ls_number_reflns 573 _refine_ls_R_factor_all 0.1208 _refine_ls_R_factor_gt 0.0486 _refine_ls_wR_factor_gt 0.0856 _refine_ls_wR_factor_ref 0.1965 _cod_data_source_file Acta-Chem-Scand-1997-51-1162-1.cif _cod_data_source_block 1 _cod_original_sg_symbol_H-M 'P 21/c' _cod_database_code 1557323 loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 x,y,z 2 -x,1/2+y,1/2-z 3 -x,-y,-z 4 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 0.2031(3) 0.7660(3) 0.1309(2) 1.000 0.0600(10) . . . . N1 N Uiso 0.4900(4) 0.5700(3) 0.0959(2) 1.000 0.0450(10) . . . . C1 C Uiso 0.6680(5) 0.5837(4) 0.0461(2) 1.000 0.0530(10) . . . . C2 C Uiso 0.3909(5) 0.4255(4) 0.0671(2) 1.000 0.0510(10) . . . . C3 C Uiso 0.5460(5) 0.5834(4) 0.2066(2) 1.000 0.0510(10) . . . . C4 C Uiso 0.3675(5) 0.5996(4) 0.2597(2) 1.000 0.0440(10) . . . . C5 C Uiso 0.2119(5) 0.6968(4) 0.2224(2) 1.000 0.0460(10) . . . . C6 C Uiso 0.0621(5) 0.7289(4) 0.2785(2) 1.000 0.0550(10) . . . . C7 C Uiso 0.0635(6) 0.6604(4) 0.3710(3) 1.000 0.0630(10) . . . . C8 C Uiso 0.2124(6) 0.5612(4) 0.4085(2) 1.000 0.0590(10) . . . . C9 C Uiso 0.3632(5) 0.5315(4) 0.3530(2) 1.000 0.0530(10) . . . . H1 H Uiso 0.291(5) 0.713(4) 0.093(3) 1.000 0.0890 . . . . 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 108.9(2) . . . yes C1 N1 C3 110.6(2) . . . yes C2 N1 C3 111.7(2) . . . yes C5 O1 H1 108(2) . . . no N1 C1 C2 110.3(3) . . 3_665 yes N1 C2 C1 110.5(3) . . 3_665 yes N1 C3 C4 112.7(3) . . . yes C3 C4 C9 121.2(3) . . . no C5 C4 C9 118.0(3) . . . no C3 C4 C5 120.5(3) . . . no O1 C5 C6 117.8(3) . . . yes C4 C5 C6 120.5(3) . . . no O1 C5 C4 121.7(3) . . . yes C5 C6 C7 119.9(3) . . . no C6 C7 C8 120.8(4) . . . no C7 C8 C9 119.1(3) . . . no C4 C9 C8 121.7(3) . . . no 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 1.362(4) . . yes N1 C1 1.467(4) . . yes N1 C2 1.460(5) . . yes N1 C3 1.478(4) . . yes O1 H1 0.96(4) . . no C1 C2 1.510(4) . 3_665 no C3 C4 1.498(5) . . no C4 C9 1.391(4) . . no C4 C5 1.385(5) . . no C5 C6 1.380(5) . . no C6 C7 1.378(5) . . no C7 C8 1.366(5) . . no C8 C9 1.376(5) . . 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 O1 H1 N1 0.96(4) 1.84(3) 2.687(4) 146(3) . 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 58.5(3) . . . 3_665 no C3 N1 C1 C2 -178.4(3) . . . 3_665 no C1 N1 C2 C1 -58.6(3) . . . 3_665 no C3 N1 C2 C1 178.9(3) . . . 3_665 no C1 N1 C3 C4 169.2(3) . . . . no C2 N1 C3 C4 -69.3(4) . . . . no N1 C1 C2 N1 -59.5(4) . . 3_665 3_665 no N1 C3 C4 C5 -44.2(4) . . . . no N1 C3 C4 C9 143.0(3) . . . . no C3 C4 C5 O1 8.2(5) . . . . no C3 C4 C5 C6 -170.5(3) . . . . no C9 C4 C5 O1 -178.9(3) . . . . no C9 C4 C5 C6 2.5(5) . . . . no C3 C4 C9 C8 171.5(3) . . . . no C5 C4 C9 C8 -1.4(5) . . . . no O1 C5 C6 C7 179.3(3) . . . . no C4 C5 C6 C7 -2.0(5) . . . . no C5 C6 C7 C8 0.4(5) . . . . no C6 C7 C8 C9 0.7(5) . . . . no C7 C8 C9 C4 -0.2(5) . . . . no