#------------------------------------------------------------------------------ #$Date: 2012-02-03 17:16:24 +0000 (Fri, 03 Feb 2012) $ #$Revision: 32112 $ #$URL: svn://www.crystallography.net/cod/cif/2/20/05/2200559.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_2200559 loop_ _publ_author_name 'Mahmoudkhani, Amir H.' 'Langer, Vratislav' _publ_section_title ; Zigzag hydrogen-bonded sheets in the structure of p-phenylazoaniline hydrochloride ; _journal_issue 9 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o839 _journal_page_last o841 _journal_volume 57 _journal_year 2001 _chemical_formula_iupac 'C12 H12 N3 1+, Cl 1-' _chemical_formula_moiety 'C12 H12 N3 1+, Cl 1-' _chemical_formula_sum 'C12 H12 Cl N3' _chemical_formula_weight 233.70 _chemical_name_systematic ; p-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' _audit_creation_method SHELXTL _cell_angle_alpha 90.00 _cell_angle_beta 111.9130(10) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 7.3718(3) _cell_length_b 18.5164(7) _cell_length_c 8.91230(10) _cell_measurement_reflns_used 2394 _cell_measurement_temperature 297(2) _cell_measurement_theta_max 25 _cell_measurement_theta_min 1 _cell_volume 1128.63(6) _computing_cell_refinement 'SAINT (Siemens, 1995)' _computing_data_collection 'SMART (Siemens, 1995)' _computing_data_reduction 'SAINT and SADABS (Sheldrick, 2001)' _computing_molecular_graphics 'DIAMOND (Brandenburg, 2000)' _computing_structure_refinement SHELXTL _computing_structure_solution 'SHELXTL (Bruker, 2001)' _diffrn_ambient_temperature 297(2) _diffrn_measured_fraction_theta_full .956 _diffrn_measured_fraction_theta_max .956 _diffrn_measurement_device_type 'Siemens SMART CCD' _diffrn_measurement_method \w _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength .71073 _diffrn_reflns_av_R_equivalents .0382 _diffrn_reflns_av_sigmaI/netI .0573 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_number 3608 _diffrn_reflns_theta_full 25.43 _diffrn_reflns_theta_max 25.43 _diffrn_reflns_theta_min 2.20 _diffrn_standards_decay_% 0 _exptl_absorpt_coefficient_mu .313 _exptl_absorpt_correction_T_max .9401 _exptl_absorpt_correction_T_min .8346 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SADABS; Sheldrick, 2001)' _exptl_crystal_colour dark-red _exptl_crystal_density_diffrn 1.375 _exptl_crystal_density_method 'not measured' _exptl_crystal_description needle _exptl_crystal_F_000 488 _exptl_crystal_size_max .60 _exptl_crystal_size_mid .20 _exptl_crystal_size_min .20 _refine_diff_density_max .398 _refine_diff_density_min -.315 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.051 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 166 _refine_ls_number_reflns 1982 _refine_ls_number_restraints 3 _refine_ls_restrained_S_all 1.052 _refine_ls_R_factor_all .0681 _refine_ls_R_factor_gt .0515 _refine_ls_shift/su_max <0.001 _refine_ls_shift/su_mean .000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w = 1/[\s^2^(Fo^2^)+(0.0885P)^2^+0.0439P] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_ref .1503 _reflns_number_gt 1476 _reflns_number_total 1982 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file wn6041.cif _[local]_cod_data_source_block I _[local]_cod_cif_authors_sg_H-M 'P 21/c' _cod_database_code 2200559 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 Cl .25125(11) .35094(3) .25208(7) .0583(3) Uani d . 1 . . Cl N1 -.1796(3) .69262(11) .1163(3) .0450(5) Uani d D 1 . . N H2 -.227(4) .6825(15) .013(2) .058(9) Uiso d D 1 . . H H1 -.212(4) .7331(11) .151(3) .055(8) Uiso d D 1 . . H N2 .2890(3) .51264(9) .5880(2) .0367(5) Uani d . 1 . . N N3 .3509(3) .44960(10) .5676(2) .0363(5) Uani d D 1 . . N H3 .322(4) .4275(13) .474(2) .053(8) Uiso d D 1 . . H C11 -.0719(3) .64667(11) .2278(3) .0357(6) Uani d . 1 . . C C12 -.0222(3) .57759(12) .1830(3) .0384(6) Uani d . 1 . . C H12 -.0707 .5641 .0747 .041(7) Uiso calc R 1 . . H C13 .0940(3) .53167(12) .2955(3) .0379(6) Uani d . 1 . . C H13 .1252 .4870 .2640 .042(6) Uiso calc R 1 . . H C14 .1692(3) .55117(11) .4622(3) .0344(5) Uani d . 1 . . C C15 .1147(3) .61907(12) .5067(3) .0394(6) Uani d . 1 . . C H15 .1603 .6321 .6153 .041(7) Uiso calc R 1 . . H C16 -.0026(3) .66536(12) .3942(3) .0386(6) Uani d . 1 . . C H16 -.0376 .7093 .4261 .049(7) Uiso calc R 1 . . H C21 .4736(3) .41061(12) .7048(3) .0348(5) Uani d . 1 . . C C22 .5158(4) .33944(13) .6843(3) .0435(6) Uani d . 1 . . C H22 .4691 .3185 .5821 .038(6) Uiso calc R 1 . . H C23 .6290(4) .29977(14) .8188(3) .0516(7) Uani d . 1 . . C H23 .6572 .2517 .8069 .059(8) Uiso calc R 1 . . H C24 .7000(4) .33110(16) .9698(3) .0555(7) Uani d . 1 . . C H24 .7746 .3039 1.0594 .078(9) Uiso calc R 1 . . H C25 .6609(4) .40211(16) .9886(3) .0562(7) Uani d . 1 . . C H25 .7110 .4232 1.0907 .071(9) Uiso calc R 1 . . H C26 .5472(4) .44282(14) .8565(3) .0466(6) Uani d . 1 . . C H26 .5206 .4910 .8692 .055(8) Uiso calc R 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 Cl .0853(6) .0381(4) .0381(4) .0054(3) .0076(4) -.0031(2) N1 .0482(13) .0401(12) .0390(14) .0084(10) .0072(10) .0050(9) N2 .0323(11) .0327(10) .0384(11) -.0019(8) .0055(8) .0013(8) N3 .0349(11) .0338(10) .0322(11) .0011(8) .0031(9) .0002(8) C11 .0320(12) .0340(12) .0394(13) -.0021(9) .0114(10) .0038(9) C12 .0398(13) .0365(12) .0323(13) .0010(10) .0058(10) -.0017(9) C13 .0391(13) .0321(11) .0381(14) .0004(10) .0096(10) -.0011(9) C14 .0295(12) .0311(11) .0358(13) -.0022(9) .0042(9) .0029(9) C15 .0442(14) .0361(12) .0321(13) -.0038(10) .0078(10) -.0032(9) C16 .0400(13) .0318(11) .0403(14) .0014(10) .0104(11) -.0018(9) C21 .0259(11) .0374(12) .0351(13) .0019(9) .0046(9) .0044(9) C22 .0391(13) .0411(13) .0417(15) .0018(10) .0051(11) -.0003(10) C23 .0452(15) .0427(14) .0597(18) .0116(12) .0112(12) .0065(12) C24 .0503(16) .0612(17) .0478(16) .0202(13) .0100(13) .0194(13) C25 .0533(17) .0669(18) .0365(15) .0169(14) .0030(12) .0010(12) C26 .0459(15) .0473(14) .0378(14) .0121(11) .0056(11) -.0001(11) 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 C11 . 1.324(3) yes N1 H2 . .878(17) ? N1 H1 . .876(17) ? N2 N3 . 1.291(3) yes N2 C14 . 1.344(3) yes N3 C21 . 1.418(3) yes N3 H3 . .879(16) ? C11 C16 . 1.420(3) ? C11 C12 . 1.428(3) ? C12 C13 . 1.350(3) ? C12 H12 . .9300 ? C13 C14 . 1.425(3) ? C13 H13 . .9300 ? C14 C15 . 1.421(3) ? C15 C16 . 1.356(3) ? C15 H15 . .9300 ? C16 H16 . .9300 ? C21 C22 . 1.382(3) ? C21 C26 . 1.389(3) ? C22 C23 . 1.388(3) ? C22 H22 . .9300 ? C23 C24 . 1.377(4) ? C23 H23 . .9300 ? C24 C25 . 1.370(4) ? C24 H24 . .9300 ? C25 C26 . 1.386(3) ? C25 H25 . .9300 ? C26 H26 . .9300 ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C .0033 .0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N .0061 .0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl .1484 .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 _geom_angle_publ_flag C11 N1 H2 123.0(19) ? C11 N1 H1 117.0(18) ? H2 N1 H1 120(3) ? N3 N2 C14 121.29(19) yes N2 N3 C21 118.97(19) yes N2 N3 H3 125.5(17) ? C21 N3 H3 115.6(17) ? N1 C11 C16 120.6(2) ? N1 C11 C12 120.7(2) ? C16 C11 C12 118.73(19) ? C13 C12 C11 121.0(2) ? C13 C12 H12 119.5 ? C11 C12 H12 119.5 ? C12 C13 C14 120.5(2) ? C12 C13 H13 119.8 ? C14 C13 H13 119.8 ? N2 C14 C15 113.79(19) ? N2 C14 C13 127.9(2) ? C15 C14 C13 118.3(2) ? C16 C15 C14 121.4(2) ? C16 C15 H15 119.3 ? C14 C15 H15 119.3 ? C15 C16 C11 120.0(2) ? C15 C16 H16 120.0 ? C11 C16 H16 120.0 ? C22 C21 C26 120.8(2) ? C22 C21 N3 118.3(2) ? C26 C21 N3 120.8(2) ? C21 C22 C23 118.9(2) ? C21 C22 H22 120.6 ? C23 C22 H22 120.6 ? C24 C23 C22 120.5(2) ? C24 C23 H23 119.7 ? C22 C23 H23 119.7 ? C25 C24 C23 120.2(2) ? C25 C24 H24 119.9 ? C23 C24 H24 119.9 ? C24 C25 C26 120.4(3) ? C24 C25 H25 119.8 ? C26 C25 H25 119.8 ? C25 C26 C21 119.1(2) ? C25 C26 H26 120.5 ? C21 C26 H26 120.5 ? 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 H1 Cl 2 .876(17) 2.405(18) 3.273(2) 171(2) N1 H2 Cl 3_565 .878(17) 2.379(19) 3.227(2) 162(2) N3 H3 Cl . .879(16) 2.330(17) 3.200(2) 170(2) C13 H13 Cl . .93 2.70 3.609(2) 165.8 C22 H22 Cl . .93 2.84 3.617(3) 141.8 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 N3 N2 C14 C13 -.2(4) yes N2 N3 C21 C26 -8.2(3) yes C21 N3 N2 C14 -178.7(2) yes