#------------------------------------------------------------------------------ #$Date: 2015-04-02 12:22:18 +0100 (Thu, 02 Apr 2015) $ #$Revision: 134621 $ #$URL: svn://www.crystallography.net/cod/cif/2/20/25/2202587.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_2202587 loop_ _publ_author_name 'Yang, Shi-Ping' 'Chen, Hong-Mei' 'Znang, Fan' 'Yu, Xi-Bin' 'Weng, lin-Hong' _publ_section_title ; N,N'-Bis(aminopropyl)-1,4-benzylidenediammonium diperchlorate ; _journal_issue 11 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o1830 _journal_page_last o1831 _journal_paper_doi 10.1107/S160053680302436X _journal_volume 59 _journal_year 2003 _chemical_formula_iupac 'C14 H24 N4 2+, 2Cl O4 1-' _chemical_formula_moiety 'C14 H24 N4 2+, 2Cl O4 1-' _chemical_formula_sum 'C14 H24 Cl2 N4 O8' _chemical_formula_weight 447.27 _chemical_name_systematic ; N,N'-Bis(aminopropyl)-1,4-benzylidenediammonium diperchlorate ; _space_group_IT_number 14 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_space_group_name_H-M 'P 1 21/c 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-97 _cell_angle_alpha 90.00 _cell_angle_beta 91.714(3) _cell_angle_gamma 90.00 _cell_formula_units_Z 2 _cell_length_a 13.358(3) _cell_length_b 7.864(2) _cell_length_c 9.313(2) _cell_measurement_reflns_used 4254 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 52.00 _cell_measurement_theta_min 3.06 _cell_volume 977.9(4) _computing_cell_refinement SMART _computing_data_collection 'SMART (Blessing, 1995)' _computing_data_reduction 'SHELXTL (Sheldrick, 1997a)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 1998)' _computing_publication_material SHELXL97 _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997b)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997b)' _diffrn_ambient_temperature 293(2) _diffrn_measured_fraction_theta_full 0.924 _diffrn_measured_fraction_theta_max 0.924 _diffrn_measurement_device_type 'Bruker SMART CCD area-detector' _diffrn_measurement_method \w _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0149 _diffrn_reflns_av_sigmaI/netI 0.0202 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_k_max 4 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_number 4254 _diffrn_reflns_theta_full 26.00 _diffrn_reflns_theta_max 26.00 _diffrn_reflns_theta_min 1.53 _diffrn_standards_decay_% none _exptl_absorpt_coefficient_mu 0.383 _exptl_absorpt_correction_T_max 0.9413 _exptl_absorpt_correction_T_min 0.8683 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SADABS; Bruker, 1998)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.519 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 468 _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.16 _refine_diff_density_max 0.631 _refine_diff_density_min -0.289 _refine_ls_extinction_coef 0.035(4) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method SHELXL97 _refine_ls_goodness_of_fit_ref 1.042 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 128 _refine_ls_number_reflns 1915 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.042 _refine_ls_R_factor_all 0.0552 _refine_ls_R_factor_gt 0.0493 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^)+(0.0709P)^2^+0.8221P] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1318 _refine_ls_wR_factor_ref 0.1384 _reflns_number_gt 1691 _reflns_number_total 1915 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file cv6238.cif _[local]_cod_data_source_block I _[local]_cod_cif_authors_sg_H-M 'P 21/c' _cod_depositor_comments ; The following automatic conversions were performed: '_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic' 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: '_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic' 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_values 1715 2011-07-08 13:25:40Z adriana The following automatic conversions were performed: '_refine_ls_weighting_scheme' value 'calc w = 1/[\s^2^(Fo^2^)+(0.0709P)^2^+0.8221P] 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^)+(0.0709P)^2^+0.8221P] where P = (Fo^2^+2Fc^2^)/3'. Automatic conversion script Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas ; _cod_database_code 2202587 _cod_database_fobs_code 2202587 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_type_symbol N1 0.15125(17) 0.9734(4) 0.1722(3) 0.0627(7) Uani d . 1 . . N N2 0.36637(15) 0.9651(3) 0.2013(2) 0.0435(5) Uani d . 1 . . N H2A 0.3072 0.9985 0.2325 0.065 Uiso d R 1 . . H H2B 0.4118 1.0454 0.2202 0.065 Uiso d R 1 . . H H2C 0.3847 0.8692 0.2455 0.065 Uiso d R 1 . . H C1 -0.09545(19) 0.9521(4) 0.5346(4) 0.0582(7) Uani d . 1 . . C H1 -0.1600 0.9201 0.5576 0.070 Uiso d R 1 . . H C2 -0.06226(19) 0.9220(4) 0.4008(3) 0.0575(7) Uani d . 1 . . C H2 -0.1044 0.8686 0.3335 0.069 Uiso d R 1 . . H C3 0.03356(18) 0.9694(4) 0.3621(3) 0.0537(7) Uani d . 1 . . C C4 0.0655(2) 0.9377(4) 0.2165(3) 0.0585(7) Uani d . 1 . . C H4 0.0198 0.8879 0.1520 0.070 Uiso d R 1 . . H C5 0.1703(2) 0.9453(5) 0.0204(4) 0.0683(9) Uani d . 1 . . C H5A 0.1755 1.0543 -0.0275 0.082 Uiso d R 1 . . H H5B 0.1141 0.8844 -0.0235 0.082 Uiso d R 1 . . H C6 0.2626(2) 0.8476(5) -0.0004(4) 0.0647(8) Uani d . 1 . . C H6A 0.2659 0.8183 -0.1013 0.078 Uiso d R 1 . . H H6B 0.2582 0.7421 0.0530 0.078 Uiso d R 1 . . H C7 0.35874(19) 0.9355(4) 0.0444(3) 0.0481(6) Uani d . 1 . . C H7A 0.4150 0.8665 0.0158 0.058 Uiso d R 1 . . H H7B 0.3626 1.0437 -0.0051 0.058 Uiso d R 1 . . H Cl1 0.37926(4) 0.08558(7) 0.63657(6) 0.0425(3) Uani d . 1 . . Cl O1 0.40930(18) -0.0678(3) 0.7055(3) 0.0689(6) Uani d . 1 . . O O2 0.46099(15) 0.2022(3) 0.6485(3) 0.0726(7) Uani d . 1 . . O O3 0.3546(2) 0.0555(4) 0.4919(2) 0.0809(7) Uani d . 1 . . O O4 0.29587(16) 0.1582(3) 0.7040(3) 0.0764(7) Uani d . 1 . . O 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 N1 0.0390(12) 0.0830(18) 0.0659(15) 0.0021(12) -0.0036(10) -0.0157(14) N2 0.0393(10) 0.0483(11) 0.0426(11) -0.0014(9) -0.0015(8) 0.0055(9) C1 0.0298(12) 0.0691(18) 0.0756(19) -0.0033(12) -0.0020(12) -0.0097(15) C2 0.0322(12) 0.0687(19) 0.0711(19) -0.0027(11) -0.0068(12) -0.0125(14) C3 0.0317(12) 0.0576(16) 0.0713(18) 0.0039(11) -0.0062(11) -0.0060(14) C4 0.0359(13) 0.0688(19) 0.0701(18) 0.0019(12) -0.0087(12) -0.0108(15) C5 0.0551(17) 0.087(2) 0.0624(18) 0.0048(16) -0.0076(14) -0.0087(17) C6 0.0576(17) 0.074(2) 0.0620(18) -0.0002(15) -0.0039(13) -0.0162(15) C7 0.0461(14) 0.0540(15) 0.0444(14) -0.0020(11) 0.0058(10) -0.0055(11) Cl1 0.0411(4) 0.0425(4) 0.0435(4) 0.0006(2) -0.0085(2) -0.0019(2) O1 0.0823(15) 0.0526(12) 0.0709(14) 0.0034(10) -0.0095(11) 0.0129(10) O2 0.0449(11) 0.0527(12) 0.1192(19) -0.0040(9) -0.0140(11) -0.0057(12) O3 0.0906(17) 0.1066(19) 0.0444(12) -0.0045(14) -0.0160(11) -0.0008(12) O4 0.0504(12) 0.0854(17) 0.0937(17) 0.0067(12) 0.0065(11) -0.0164(14) 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' Cl Cl 0.1484 0.1585 '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_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C4 N1 C5 . . 118.0(3) yes C7 N2 H2A . . 109.5 ? C7 N2 H2B . . 109.5 ? H2A N2 H2B . . 109.5 ? C7 N2 H2C . . 109.5 ? H2A N2 H2C . . 109.5 ? H2B N2 H2C . . 109.5 ? C2 C1 C3 . 3_576 120.5(3) yes C2 C1 H1 . . 119.7 ? C3 C1 H1 3_576 . 119.7 ? C1 C2 C3 . . 121.3(3) yes C1 C2 H2 . . 119.3 ? C3 C2 H2 . . 119.3 ? C2 C3 C1 . 3_576 118.2(3) yes C2 C3 C4 . . 119.5(3) yes C1 C3 C4 3_576 . 122.3(3) yes N1 C4 C3 . . 124.2(3) yes N1 C4 H4 . . 117.9 ? C3 C4 H4 . . 117.9 ? N1 C5 C6 . . 112.2(3) yes N1 C5 H5A . . 109.2 ? C6 C5 H5A . . 109.2 ? N1 C5 H5B . . 109.2 ? C6 C5 H5B . . 109.2 ? H5A C5 H5B . . 107.9 ? C5 C6 C7 . . 115.8(3) yes C5 C6 H6A . . 108.3 ? C7 C6 H6A . . 108.3 ? C5 C6 H6B . . 108.3 ? C7 C6 H6B . . 108.3 ? H6A C6 H6B . . 107.4 ? N2 C7 C6 . . 112.3(2) yes N2 C7 H7A . . 109.2 ? C6 C7 H7A . . 109.1 ? N2 C7 H7B . . 109.2 ? C6 C7 H7B . . 109.1 ? H7A C7 H7B . . 107.9 ? O3 Cl1 O4 . . 109.27(15) ? O3 Cl1 O1 . . 110.32(15) ? O4 Cl1 O1 . . 110.99(16) ? O3 Cl1 O2 . . 109.99(16) ? O4 Cl1 O2 . . 108.44(14) ? O1 Cl1 O2 . . 107.79(14) ? 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 C4 . 1.261(4) yes N1 C5 . 1.460(4) yes N2 C7 . 1.480(3) yes N2 H2A . 0.8900 ? N2 H2B . 0.8900 ? N2 H2C . 0.8900 ? C1 C2 . 1.356(4) yes C1 C3 3_576 1.394(4) ? C1 H1 . 0.9300 ? C2 C3 . 1.391(4) yes C2 H2 . 0.9300 ? C3 C1 3_576 1.394(4) yes C3 C4 . 1.456(4) yes C4 H4 . 0.9300 ? C5 C6 . 1.471(4) yes C5 H5A . 0.9700 ? C5 H5B . 0.9700 ? C6 C7 . 1.506(4) yes C6 H6A . 0.9701 ? C6 H6B . 0.9700 ? C7 H7A . 0.9700 ? C7 H7B . 0.9700 ? Cl1 O3 . 1.397(2) ? Cl1 O4 . 1.415(2) ? Cl1 O1 . 1.419(2) ? Cl1 O2 . 1.427(2) ? 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_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA N2 H2C O1 4_565 0.89 2.42 3.176(3) 143 N2 H2C O2 3_666 0.89 2.33 2.968(3) 129 N2 H2B O1 3_666 0.89 2.47 3.199(3) 139 N2 H2B O2 4_575 0.89 2.20 2.953(3) 142 N2 H2A N1 . 0.89 2.15 2.879(3) 139 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_site_symmetry_1 _geom_torsion_site_symmetry_4 _geom_torsion _geom_torsion_publ_flag C3 C1 C2 C3 3_576 . -0.5(5) yes C1 C2 C3 C1 . 3_576 0.5(5) ? C1 C2 C3 C4 . . -178.8(3) ? C5 N1 C4 C3 . . -175.8(3) ? C2 C3 C4 N1 . . -178.8(3) ? C1 C3 C4 N1 3_576 . 1.9(5) ? C4 N1 C5 C6 . . -129.8(3) ? N1 C5 C6 C7 . . -66.6(4) ? C5 C6 C7 N2 . . 65.6(4) ?