#------------------------------------------------------------------------------ #$Date: 2025-08-18 23:52:38 +0100 (Mon, 18 Aug 2025) $ #$Revision: 301791 $ #$URL: svn://www.crystallography.net/cod/cif/2/00/83/2008368.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/. The original data for this entry # were provided by IUCr Journals, http://journals.iucr.org/. # # The file may be used within the scientific community so long as # proper attribution is given to the journal article from which the # data were obtained. # data_2008368 loop_ _publ_author_name 'Sarmistha Basu Majumder' 'Monika Mukherjee' 'Goutam Kumar Patra' 'Dipankar Datta' 'Madeleine Helliwell' _publ_section_title ; 2-(2,3-Diphenylpiperazin-1-yl)ethylammonium chloride ; _journal_issue 4 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 668 _journal_page_last 670 _journal_paper_doi 10.1107/S0108270198017648 _journal_volume 55 _journal_year 1999 _chemical_formula_analytical 'C18 H24 Cl N3' _chemical_formula_moiety 'C18 H24 N3 +.Cl- ' _chemical_formula_structural 'C18 H24 Cl N3' _chemical_formula_sum 'C18 H24 Cl N3' _chemical_formula_weight 317.85 _chemical_name_systematic ; 1-(2-aminoethyl)-2,3-diphenylpiperazine hydrochloride ; _space_group_IT_number 61 _symmetry_cell_setting orthorhombic _symmetry_space_group_name_Hall '-P 2ac 2ab' _symmetry_space_group_name_H-M 'P b c a' _audit_creation_method SHELXL _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_formula_units_Z 8 _cell_length_a 13.585(2) _cell_length_b 35.391(7) _cell_length_c 7.067(2) _cell_measurement_reflns_used 25 _cell_measurement_temperature 296.2 _cell_measurement_theta_max 20 _cell_measurement_theta_min 14 _cell_volume 3397.7(13) _computing_cell_refinement 'MSC/AFC Diffractometer Control' _computing_data_collection 'MSC/AFC Diffractometer Control (Molecular Structure Corporation, 1993)' _computing_data_reduction 'TEXSAN (Molecular Structure Corporation, 1995)' _computing_molecular_graphics 'ZORTEP (Zsolnai, 1995)' _computing_publication_material SHELXL93 _computing_structure_refinement 'SHELXL93 (Sheldrick, 1993)' _computing_structure_solution 'MULTAN-88 (Debaerdemaeker et al., 1988)' _diffrn_ambient_temperature 296.2 _diffrn_measurement_device 'Rigaku AFC5R' _diffrn_measurement_method \w--2\q _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'Rigaku rotating anode' _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54180 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0513 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_k_max 45 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_number 3378 _diffrn_reflns_theta_max 79.40 _diffrn_reflns_theta_min 5.00 _diffrn_standards_decay_% <1.5 _diffrn_standards_interval_count 150 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu 1.976 _exptl_absorpt_correction_T_max 0.743 _exptl_absorpt_correction_T_min 0.634 _exptl_absorpt_correction_type 'empirical (North et al., 1968)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.243 _exptl_crystal_density_meas ? _exptl_crystal_density_method none _exptl_crystal_description Prism _exptl_crystal_F_000 1360 _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.15 _refine_diff_density_max 0.252 _refine_diff_density_min -0.273 _refine_ls_extinction_coef none _refine_ls_extinction_method none _refine_ls_goodness_of_fit_all 1.056 _refine_ls_goodness_of_fit_obs 1.042 _refine_ls_hydrogen_treatment refU _refine_ls_matrix_type full _refine_ls_number_parameters 221 _refine_ls_number_reflns 3344 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.594 _refine_ls_restrained_S_obs 1.042 _refine_ls_R_factor_all 0.1400 _refine_ls_R_factor_obs 0.0561 _refine_ls_shift/esd_max 0.028 _refine_ls_shift/esd_mean 0.002 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^)+(0.0615P)^2^+4.0173P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_all 0.2646 _refine_ls_wR_factor_obs 0.1371 _reflns_number_observed 2176 _reflns_number_total 3378 _reflns_observed_criterion >2sigma(I) _cod_data_source_file ha1247.cif _cod_data_source_block Piperazine.HCl _cod_depositor_comments ; The following automatic conversions were performed: '_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic' according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29. Automatic conversion script Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius The following automatic conversions were performed: '_exptl_crystal_density_meas' value 'not measured' was changed to '?' - the value is perceived as not measured. Automatic conversion script Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas The following automatic conversions were performed: '_refine_ls_weighting_scheme' value 'calc w = 1/[\s^2^(Fo^2^)+(0.0615P)^2^+4.0173P] where P=(Fo^2^+2Fc^2^)/3' was changed to 'calc'. New tag '_refine_ls_weighting_details' was created. The value of the new tag was set to 'w = 1/[\s^2^(Fo^2^)+(0.0615P)^2^+4.0173P] where P=(Fo^2^+2Fc^2^)/3'. Automatic conversion script Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas ; _cod_original_cell_volume 3398.0(10) _cod_database_code 2008368 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x+1/2, -y, z+1/2' '-x, -y, -z' '-x-1/2, y-1/2, z' 'x, -y-1/2, z-1/2' 'x-1/2, y, -z-1/2' loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 Cl 0.0618(5) 0.0490(5) 0.0469(5) 0.0013(4) 0.0019(5) 0.0019(4) N1 0.0435(15) 0.0432(15) 0.039(2) 0.0008(12) 0.0040(14) -0.0016(14) N2 0.0347(13) 0.0381(13) 0.041(2) -0.0026(11) -0.0013(13) 0.0011(12) N3 0.0365(14) 0.051(2) 0.051(2) -0.0013(12) 0.0017(14) 0.0032(14) C1 0.047(2) 0.041(2) 0.040(2) -0.0015(15) 0.004(2) -0.0026(15) C2 0.056(2) 0.047(2) 0.049(2) 0.002(2) 0.002(2) 0.000(2) C3 0.077(3) 0.048(2) 0.055(3) 0.011(2) 0.005(2) 0.005(2) C4 0.085(3) 0.043(2) 0.067(3) -0.008(2) 0.017(3) 0.001(2) C5 0.065(3) 0.067(3) 0.073(3) -0.024(2) 0.006(2) -0.003(2) C6 0.052(2) 0.058(2) 0.055(2) -0.009(2) -0.003(2) 0.007(2) C7 0.037(2) 0.038(2) 0.040(2) -0.0003(13) -0.002(2) -0.0004(15) C8 0.045(2) 0.036(2) 0.056(2) 0.0032(15) -0.002(2) -0.003(2) C9 0.041(2) 0.037(2) 0.055(2) -0.0003(14) -0.007(2) 0.004(2) C10 0.046(2) 0.055(2) 0.039(2) -0.005(2) -0.001(2) 0.000(2) C11 0.045(2) 0.060(2) 0.045(2) -0.002(2) -0.002(2) 0.009(2) C12 0.033(2) 0.0358(15) 0.042(2) -0.0042(13) -0.0016(15) -0.0025(14) C13 0.040(2) 0.042(2) 0.040(2) -0.0013(14) 0.005(2) 0.0013(15) C14 0.044(2) 0.045(2) 0.052(2) 0.0018(15) -0.001(2) -0.002(2) C15 0.047(2) 0.063(2) 0.061(3) 0.011(2) -0.001(2) 0.004(2) C16 0.071(3) 0.056(2) 0.075(3) 0.022(2) 0.004(3) -0.004(2) C17 0.080(3) 0.044(2) 0.073(3) 0.005(2) 0.002(3) -0.015(2) C18 0.053(2) 0.048(2) 0.060(3) -0.002(2) -0.002(2) -0.006(2) loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_thermal_displace_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_disorder_group _atom_site_type_symbol Cl 0.36663(7) 0.21005(2) 0.06956(14) 0.0525(3) Uani d . 1 . Cl N1 0.2382(2) 0.32845(8) -0.0691(4) 0.0420(7) Uani d . 1 . N N2 0.0923(2) 0.32753(7) 0.2226(4) 0.0379(6) Uani d . 1 . N N3 -0.0850(2) 0.29555(8) 0.3798(4) 0.0462(7) Uani d . 1 . N C1 0.2074(3) 0.39631(10) -0.1286(5) 0.0426(8) Uani d . 1 . C C2 0.1506(3) 0.41894(10) -0.2452(6) 0.0504(9) Uani d . 1 . C C3 0.1821(3) 0.45455(11) -0.2978(6) 0.0600(11) Uani d . 1 . C C4 0.2712(4) 0.46786(11) -0.2365(7) 0.0649(12) Uani d . 1 . C C5 0.3291(3) 0.44580(13) -0.1251(7) 0.0683(12) Uani d . 1 . C C6 0.2980(3) 0.41028(11) -0.0694(6) 0.0547(10) Uani d . 1 . C C7 0.1665(2) 0.35932(9) -0.0564(5) 0.0385(8) Uani d . 1 . C C8 0.1870(3) 0.29348(9) -0.0200(6) 0.0454(9) Uani d . 1 . C C9 0.1580(2) 0.29540(9) 0.1845(5) 0.0442(8) Uani d . 1 . C C10 0.0706(3) 0.33042(10) 0.4247(5) 0.0467(8) Uani d . 1 . C C11 0.0068(3) 0.29817(11) 0.4932(6) 0.0502(9) Uani d . 1 . C C12 0.1323(2) 0.36346(9) 0.1502(5) 0.0369(7) Uani d . 1 . C C13 0.0550(2) 0.39408(9) 0.1596(5) 0.0405(8) Uani d . 1 . C C14 -0.0389(3) 0.38711(10) 0.0893(6) 0.0469(9) Uani d . 1 . C C15 -0.1072(3) 0.41573(11) 0.0802(6) 0.0571(10) Uani d . 1 . C C16 -0.0833(3) 0.45180(12) 0.1394(7) 0.0674(12) Uani d . 1 . C C17 0.0085(4) 0.45856(11) 0.2121(7) 0.0658(12) Uani d . 1 . C C18 0.0775(3) 0.42986(10) 0.2226(6) 0.0535(10) Uani d . 1 . C H1 0.2584 0.3277 -0.1842 0.042(10) Uiso d . 1 . H H3A -0.1244 0.2749 0.4256 0.119(12) Uiso d . 1 . H H3B -0.0687 0.2913 0.2495 0.119(12) Uiso d . 1 . H H3C -0.1213 0.3187 0.3916 0.119(12) Uiso d . 1 . H H2 0.0902 0.4101 -0.2889 0.049(11) Uiso d . 1 . H H3 0.1427 0.4695 -0.3748 0.061(12) Uiso d . 1 . H H4 0.2914 0.4920 -0.2708 0.067(12) Uiso d . 1 . H H5 0.3905 0.4545 -0.0876 0.079(14) Uiso d . 1 . H H6 0.3377 0.3957 0.0089 0.058(12) Uiso d . 1 . H H7 0.1092 0.3528 -0.1339 0.041(9) Uiso d . 1 . H H8A 0.2300 0.2720 -0.0412 0.037(9) Uiso d . 1 . H H8B 0.1289 0.2904 -0.0984 0.048(10) Uiso d . 1 . H H9A 0.1251 0.2721 0.2201 0.051(10) Uiso d . 1 . H H9B 0.2168 0.2978 0.2619 0.053(11) Uiso d . 1 . H H10A 0.0375 0.3542 0.4492 0.075(14) Uiso d . 1 . H H10B 0.1321 0.3305 0.4951 0.052(11) Uiso d . 1 . H H11A 0.0430 0.2746 0.4830 0.056(12) Uiso d . 1 . H H11B -0.0097 0.3020 0.6253 0.070(13) Uiso d . 1 . H H12 0.1885 0.3709 0.2287 0.035(9) Uiso d . 1 . H H14 -0.0557 0.3630 0.0475 0.042(9) Uiso d . 1 . H H15 -0.1701 0.4107 0.0344 0.054(11) Uiso d . 1 . H H16 -0.1292 0.4712 0.1301 0.092(16) Uiso d . 1 . H H17 0.0245 0.4826 0.2552 0.069(13) Uiso d . 1 . H H18 0.1396 0.4348 0.2728 0.061(12) Uiso d . 1 . H loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' C C 0.0181 0.0091 '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' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_publ_flag C8 N1 C7 107.5(3) yes C8 N1 H1 110.5 no C7 N1 H1 107.1 no C10 N2 C9 110.8(3) yes C10 N2 C12 110.7(3) yes C9 N2 C12 112.3(2) yes C11 N3 H3A 109.4 no C11 N3 H3B 109.5 no H3A N3 H3B 109.6 no C11 N3 H3C 109.3 no H3A N3 H3C 109.5 no H3B N3 H3C 109.6 no C2 C1 C6 117.8(3) no C2 C1 C7 119.8(3) no C6 C1 C7 122.1(3) no C3 C2 C1 121.0(4) no C3 C2 H2 119.4 no C1 C2 H2 119.6 no C4 C3 C2 120.1(4) no C4 C3 H3 119.9 no C2 C3 H3 119.9 no C5 C4 C3 119.9(4) no C5 C4 H4 120.5 no C3 C4 H4 119.7 no C4 C5 C6 120.6(4) no C4 C5 H5 119.6 no C6 C5 H5 119.8 no C5 C6 C1 120.5(4) no C5 C6 H6 119.8 no C1 C6 H6 119.7 no N1 C7 C1 112.4(3) yes N1 C7 C12 109.2(3) yes C1 C7 C12 110.4(3) yes N1 C7 H7 108.5 no C1 C7 H7 108.0 no C12 C7 H7 108.2 no N1 C8 C9 108.4(3) yes N1 C8 H8A 109.9 no C9 C8 H8A 110.0 no N1 C8 H8B 110.4 no C9 C8 H8B 110.0 no H8A C8 H8B 108.2 no N2 C9 C8 111.8(3) yes N2 C9 H9A 109.3 no C8 C9 H9A 109.4 no N2 C9 H9B 109.2 no C8 C9 H9B 109.3 no H9A C9 H9B 107.8 no N2 C10 C11 112.0(3) yes N2 C10 H10A 109.2 no C11 C10 H10A 109.3 no N2 C10 H10B 109.1 no C11 C10 H10B 109.2 no H10A C10 H10B 107.8 no N3 C11 C10 110.8(3) yes N3 C11 H11A 109.4 no C10 C11 H11A 109.5 no N3 C11 H11B 109.6 no C10 C11 H11B 109.6 no H11A C11 H11B 108.0 no N2 C12 C13 110.3(3) yes N2 C12 C7 111.0(3) yes C13 C12 C7 108.6(3) yes N2 C12 H12 108.9 no C13 C12 H12 108.9 no C7 C12 H12 109.1 no C18 C13 C14 118.8(3) no C18 C13 C12 121.3(3) no C14 C13 C12 119.7(3) no C15 C14 C13 120.3(3) no C15 C14 H14 119.7 no C13 C14 H14 120.0 no C14 C15 C16 120.5(4) no C14 C15 H15 119.7 no C16 C15 H15 119.7 no C17 C16 C15 119.2(4) no C17 C16 H16 120.5 no C15 C16 H16 120.3 no C16 C17 C18 120.6(4) no C16 C17 H17 119.6 no C18 C17 H17 119.8 no C13 C18 C17 120.5(4) no C13 C18 H18 119.8 no C17 C18 H18 119.7 no loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag N1 C8 . 1.462(4) yes N1 C7 . 1.466(4) yes N1 H1 . 0.859 no N2 C10 . 1.462(5) yes N2 C9 . 1.470(4) yes N2 C12 . 1.475(4) yes N3 C11 . 1.486(5) yes N3 H3A . 0.960 no N3 H3B . 0.959 no N3 H3C . 0.960 no C1 C2 . 1.384(5) no C1 C6 . 1.390(5) no C1 C7 . 1.511(5) yes C2 C3 . 1.382(5) no C2 H2 . 0.931 no C3 C4 . 1.369(6) no C3 H3 . 0.928 no C4 C5 . 1.360(6) no C4 H4 . 0.928 no C5 C6 . 1.384(6) no C5 H5 . 0.928 no C6 H6 . 0.929 no C7 C12 . 1.540(5) yes C7 H7 . 0.980 no C8 C9 . 1.499(5) yes C8 H8A . 0.971 no C8 H8B . 0.971 no C9 H9A . 0.970 no C9 H9B . 0.972 no C10 C11 . 1.513(5) yes C10 H10A . 0.969 no C10 H10B . 0.972 no C11 H11A . 0.971 no C11 H11B . 0.969 no C12 C13 . 1.511(4) yes C12 H12 . 0.980 no C13 C18 . 1.377(5) no C13 C14 . 1.391(5) no C14 C15 . 1.375(5) no C14 H14 . 0.933 no C15 C16 . 1.382(6) no C15 H15 . 0.931 no C16 C17 . 1.370(6) no C16 H16 . 0.931 no C17 C18 . 1.384(5) no C17 H17 . 0.931 no C18 H18 . 0.932 no loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_distance_DH _geom_hbond_distance_DA _geom_hbond_angle_DHA N3 H3C N1 8_556 0.96 2.985(4) 126.8 N3 H3A Cl 8_556 0.96 3.117(3) 142.5 N3 H3B Cl 2_455 0.96 3.249(3) 144.5 N1 H1 Cl 7_565 0.86 3.380(3) 144.9 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_publ_flag C6 C1 C2 C3 -1.2(6) no C7 C1 C2 C3 173.5(4) no C1 C2 C3 C4 0.7(6) no C2 C3 C4 C5 0.7(7) no C3 C4 C5 C6 -1.5(7) no C4 C5 C6 C1 0.9(7) no C2 C1 C6 C5 0.4(6) no C7 C1 C6 C5 -174.1(4) no C8 N1 C7 C1 -172.5(3) no C8 N1 C7 C12 64.5(3) yes C2 C1 C7 N1 135.9(3) no C6 C1 C7 N1 -49.7(5) no C2 C1 C7 C12 -101.9(4) no C6 C1 C7 C12 72.6(4) no C7 N1 C8 C9 -66.4(3) yes C10 N2 C9 C8 -176.0(3) no C12 N2 C9 C8 -51.6(4) yes N1 C8 C9 N2 60.1(4) yes C9 N2 C10 C11 -69.0(4) no C12 N2 C10 C11 165.7(3) no N2 C10 C11 N3 -55.1(4) yes C10 N2 C12 C13 -66.1(3) no C9 N2 C12 C13 169.5(3) no C10 N2 C12 C7 173.4(3) no C9 N2 C12 C7 49.0(3) yes N1 C7 C12 N2 -55.9(3) yes C1 C7 C12 N2 -180.0(3) no N1 C7 C12 C13 -177.3(2) no C1 C7 C12 C13 58.6(3) yes N2 C12 C13 C18 136.6(4) no C7 C12 C13 C18 -101.5(4) no N2 C12 C13 C14 -48.6(4) no C7 C12 C13 C14 73.3(4) no C18 C13 C14 C15 1.1(6) no C12 C13 C14 C15 -173.8(4) no C13 C14 C15 C16 0.4(7) no C14 C15 C16 C17 -1.7(7) no C15 C16 C17 C18 1.4(8) no C14 C13 C18 C17 -1.4(6) no C12 C13 C18 C17 173.3(4) no C16 C17 C18 C13 0.2(7) no loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 21105697 2 PubChem 139056524