#------------------------------------------------------------------------------ #$Date: 2012-02-03 17:16:24 +0000 (Fri, 03 Feb 2012) $ #$Revision: 32112 $ #$URL: svn://www.crystallography.net/cod/cif/2/01/10/2011084.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_2011084 loop_ _publ_author_name 'Yatsenko, A. V.' 'Chernyshev, V. V.' 'Kurbakov, A. I.' 'Schenk, H.' _publ_section_title ; p-Phenylazoaniline hydrochloride from powder data: protonation site and UV--visible spectra ; _journal_issue 7 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 892 _journal_page_last 894 _journal_volume 56 _journal_year 2000 _chemical_formula_moiety 'C12 H12 N3 1+, Cl 1-' _chemical_formula_sum 'C12 H12 Cl N3' _chemical_formula_weight 233.70 _chemical_name_systematic ; 4-Phenylazoaniline hydrochloride ; _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' _cell_angle_alpha 90 _cell_angle_beta 111.91(2) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 7.400(3) _cell_length_b 18.511(5) _cell_length_c 8.920(3) _cell_measurement_temperature 295(2) _cell_volume 1133.6(7) _computing_cell_refinement 'LSPAID (Visser, 1986)' _computing_data_collection 'home-written program' _computing_molecular_graphics 'PLUTON (Spek, 1992)' _computing_publication_material 'PARST (Nardelli, 1983)' _computing_structure_refinement MRIA _computing_structure_solution 'MRIA (Zlokazov & Chernyshev, 1992)' _diffrn_ambient_temperature 295(2) _diffrn_measurement_device_type ; DRON-3M (Burevestnik, Russia) horizontal diffractometer ; _diffrn_radiation_monochromator 'Ni filtered' _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.5418 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 5 _diffrn_reflns_limit_l_min -5 _diffrn_reflns_number 465 _exptl_absorpt_coefficient_mu 2.768 _exptl_absorpt_correction_type none _exptl_crystal_density_diffrn 1.369 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 488 _refine_diff_density_max .8 _refine_diff_density_min -1.2 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_all 1.75 _refine_ls_hydrogen_treatment noref _refine_ls_matrix_type fullcycle _refine_ls_number_constraints 0 _refine_ls_number_parameters 109 _refine_ls_number_restraints 20 _refine_ls_shift/su_max .06 _refine_ls_shift/su_mean .03 _refine_ls_structure_factor_coef Inet _refine_ls_weighting_scheme sigma _reflns_number_total 465 _[local]_cod_data_source_file br1286.cif _[local]_cod_data_source_block I _[local]_cod_cif_authors_sg_H-M 'P 21/c' _[local]_cod_chemical_formula_sum_orig 'C12 H12 Cl1 N3' _cod_original_cell_volume 1133.7(9) _cod_database_code 2011084 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 'x, y, z' 2 '-x, y+1/2, -z+1/2' 3 '-x, -y, -z' 4 '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_thermal_displace_type _atom_site_occupancy _atom_site_type_symbol Cl1 .2501(4) .1475(2) .2491(3) .074(2) Uani 1 Cl N1 .683(2) .6999(8) .884(2) .086(6) Uiso 1 N N2 .220(2) .5154(8) .422(2) .085(6) Uiso 1 N N3 .161(2) .4527(7) .427(2) .077(6) Uiso 1 N C1 .590(2) .6516(9) .775(2) .078(6) Uiso 1 C C2 .525(2) .5840(9) .820(2) .046(6) Uiso 1 C C3 .415(2) .5393(8) .710(2) .081(7) Uiso 1 C C4 .340(2) .5535(8) .540(2) .029(6) Uiso 1 C C5 .389(2) .6239(5) .493(2) .038(6) Uiso 1 C C6 .508(2) .6687(9) .603(2) .103(8) Uiso 1 C C7 .023(2) .4153(9) .294(2) .089(9) Uiso 1 C C8 -.052(3) .4490(10) .136(2) .160(10) Uiso 1 C C9 -.160(3) .4044(9) .011(2) .108(8) Uiso 1 C C10 -.191(2) .3317(8) .030(2) .042(6) Uiso 1 C C11 -.129(2) .3024(7) .184(2) .082(7) Uiso 1 C C12 -.012(2) .3424(9) .3160(10) .063(6) Uiso 1 C H2 .568 .570 .946 .076 Uiso 1 H H3 .379 .488 .750 .076 Uiso 1 H H5 .328 .640 .368 .076 Uiso 1 H H6 .545 .720 .563 .076 Uiso 1 H H8 -.026 .505 .118 .076 Uiso 1 H H9 -.224 .427 -.109 .076 Uiso 1 H H10 -.262 .298 -.075 .076 Uiso 1 H H11 -.173 .248 .201 .076 Uiso 1 H H12 .052 .318 .434 .076 Uiso 1 H H13 .217 .426 .536 .076 Uiso 1 H H14 .729 .748 .852 .076 Uiso 1 H H15 .741 .688 1.006 .076 Uiso 1 H 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 Cl1 .115(3) .038(3) .040(3) .033(9) -.012(5) .016(9) 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 C1 . 1.32(2) no N1 H14 . 1.03 no N1 H15 . 1.03 no N2 N3 . 1.25(2) no N2 C4 . 1.31(2) no N3 C7 . 1.42(2) no N3 H13 . 1.03 no C1 C2 . 1.45(2) no C1 C6 . 1.45(2) no C2 C3 . 1.31(2) no C2 H2 . 1.08 no C3 C4 . 1.43(2) no C3 H3 . 1.08 no C4 C5 . 1.45(2) no C5 C6 . 1.33(2) no C5 H5 . 1.08 no C6 H6 . 1.08 no C7 C8 . 1.45(2) no C7 C12 . 1.40(2) no C8 C9 . 1.38(2) no C8 H8 . 1.08 no C9 C10 . 1.38(2) no C9 H9 . 1.08 no C10 C11 . 1.39(2) no C10 H10 . 1.08 no C11 C12 . 1.39(2) no C11 H11 . 1.08 no C12 H12 . 1.08 no loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source Cl Cl .348 .702 'International Tables for X-Ray Crystallography (Vol. IV)' N N .029 .018 'International Tables for X-Ray Crystallography (Vol. IV)' C C .017 .009 'International Tables for X-Ray Crystallography (Vol. IV)' H H .000 .000 'International Tables for X-Ray Crystallography (Vol. IV)' 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 H14 N1 H15 116 no C1 N1 H15 121 no C1 N1 H14 122 no N3 N2 C4 128.0(10) no N2 N3 H13 118 no N2 N3 C7 125.0(10) no C7 N3 H13 118 no N1 C1 C6 122.0(10) no N1 C1 C2 121(2) no C2 C1 C6 115.0(10) no C1 C2 H2 120 no C1 C2 C3 121(2) no C3 C2 H2 120 no C2 C3 H3 118 no C2 C3 C4 125.0(10) no C4 C3 H3 118 no N2 C4 C3 130.0(10) no C3 C4 C5 115.0(10) no N2 C4 C5 115.0(10) no C4 C5 H5 120 no C4 C5 C6 121.0(10) no C6 C5 H5 120 no C1 C6 C5 123.0(10) no C5 C6 H6 119 no C1 C6 H6 119 no N3 C7 C12 118.0(10) no N3 C7 C8 120.0(10) no C8 C7 C12 122.0(10) no C7 C8 H8 123 no C7 C8 C9 115(2) no C9 C8 H8 123 no C8 C9 H9 118 no C8 C9 C10 124(2) no C10 C9 H9 118 no C9 C10 H10 120 no C9 C10 C11 119.0(10) no C11 C10 H10 120 no C10 C11 H11 120 no C10 C11 C12 120.0(10) no C12 C11 H11 120 no C7 C12 C11 119.0(10) no C11 C12 H12 121 no C7 C12 H12 121 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_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA N1 H14 Cl1 3_666 1.03 2.17 3.18(2) 166 N1 H15 Cl1 2_656 1.03 2.29 3.27(2) 158 N3 H13 Cl1 4_555 1.03 2.27 3.27(2) 163