#------------------------------------------------------------------------------ #$Date: 2025-08-19 11:01:59 +0100 (Tue, 19 Aug 2025) $ #$Revision: 301802 $ #$URL: svn://www.crystallography.net/cod/cif/2/10/18/2101892.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_2101892 loop_ _publ_author_name 'Harada, J.' 'Ogawa, K.' 'Tomoda, S.' _publ_section_title ; Molecular Motion and Conformational Interconversion of Azobenzenes in Crystals as Studied by X-ray Diffraction ; _journal_issue 4 _journal_name_full 'Acta Crystallographica Section B' _journal_page_first 662 _journal_page_last 672 _journal_paper_doi 10.1107/S0108768197002772 _journal_volume 53 _journal_year 1997 _chemical_formula_moiety 'C14 H14 N2' _chemical_formula_sum 'C14 H14 N2' _chemical_formula_weight 210.28 _chemical_melting_point 325 _space_group_IT_number 61 _space_group_name_Hall '-P 2ac 2ab' _space_group_name_H-M_alt 'P b c a' _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 4 _cell_length_a 13.819(3) _cell_length_b 11.805(3) _cell_length_c 7.5010(12) _cell_measurement_reflns_used 25 _cell_measurement_temperature 296 _cell_measurement_theta_max 11.3 _cell_measurement_theta_min 10.4 _cell_volume 1223.6(4) _computing_cell_refinement MSC/AFC _computing_data_collection ; Rigaku AFC6A, MSC/AFC Diffractometer Control Software ; _computing_data_reduction ; DIFDAT_ADDREF_SORTRF (Xtal: Stewart, Merom, Holden, Doherty, Hall Maslen, Spadaccini & Davenport) ; _computing_molecular_graphics ' ORTEP (Xtal: Davenport, Hall & Dreissig)' _computing_publication_material 'SHELXL-93 (Sheldrick, 1993)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_structure_solution 'SIR92 (Giacobazzo,1992)' _diffrn_ambient_temperature 296 _diffrn_measurement_device Rigaku_AFC6A _diffrn_measurement_method \q/2\q _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type Mo_K\a _diffrn_radiation_wavelength .71073 _diffrn_reflns_av_R_equivalents .0000 _diffrn_reflns_av_sigmaI/netI .0490 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 0 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_number 1403 _diffrn_reflns_theta_max 27.49 _diffrn_reflns_theta_min 2.95 _diffrn_standards_decay_% 5 _diffrn_standards_interval_count 150 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu .068 _exptl_absorpt_correction_type none _exptl_crystal_colour red _exptl_crystal_density_diffrn 1.141 _exptl_crystal_description rectangular _exptl_crystal_F_000 448 _exptl_crystal_size_max .30 _exptl_crystal_size_mid .30 _exptl_crystal_size_min .25 _refine_diff_density_max .144 _refine_diff_density_min -.222 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_all 1.015 _refine_ls_goodness_of_fit_obs 1.234 _refine_ls_hydrogen_treatment ; Hydrogen atoms were ridden on the bonded carbon atoms. ; _refine_ls_matrix_type full _refine_ls_number_parameters 71 _refine_ls_number_reflns 1403 _refine_ls_number_restraints 5 _refine_ls_restrained_S_all 1.015 _refine_ls_restrained_S_obs 1.231 _refine_ls_R_factor_all .1578 _refine_ls_R_factor_obs .0653 _refine_ls_shift/esd_max -.732 _refine_ls_shift/esd_mean .051 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.1143P)^2^+0.1794P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_all .2385 _refine_ls_wR_factor_obs .1908 _reflns_number_observed 637 _reflns_number_total 1403 _reflns_observed_criterion >2sigma(I) _cod_data_source_file oa0007.cif _cod_depositor_comments ; The following automatic conversions were performed: '_refine_ls_weighting_scheme' value 'calc w=1/[\s^2^(Fo^2^)+(0.1143P)^2^+0.1794P] 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^)+(0.1143P)^2^+0.1794P] 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 2101892 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z-1/2' '-x-1/2, y-1/2, z' 'x, -y-1/2, 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 N1A .087(2) .060(2) .071(2) .000(2) -.004(2) -.0021(13) C1A .094(2) .054(2) .056(2) -.002(2) -.0008(14) .0017(14) C2A .090(2) .063(2) .063(2) -.005(2) .013(2) .0035(14) C3A .093(2) .075(2) .063(2) .004(2) .014(2) .004(2) C4A .105(3) .074(2) .067(2) .014(2) .013(2) -.001(2) C5A .124(3) .074(2) .069(2) .004(2) .002(2) -.015(2) C6A .101(3) .073(2) .068(2) .000(2) -.011(2) -.008(2) C7A .090(3) .099(3) .112(3) .003(2) .019(2) -.010(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 N1A .0423(2) 1.0165(2) .5117(4) .0729(8) Uani d PD .92 1 N C1A .11393(14) .9363(2) .4624(3) .0679(9) Uani d PGD .92 1 C C2A .2095(2) .96854(13) .4982(3) .0720(9) Uani d PGD .92 1 C H2A .2222(2) 1.0390(2) .5486(4) .086 Uiso calc PR .92 1 H C3A .28574(12) .8948(2) .4583(3) .0768(10) Uani d PG .92 1 C C4A .2665(2) .7887(2) .3825(3) .0822(11) Uani d PG .92 1 C H4A .3172(2) .7397(2) .3560(4) .099 Uiso calc PR .92 1 H C5A .1710(2) .75650(14) .3467(4) .0887(11) Uani d PG .92 1 C H5A .1582(3) .6861(2) .2964(5) .106 Uiso calc PR .92 1 H C6A .09468(14) .8303(2) .3867(3) .0808(10) Uani d PG .92 1 C H6A .0312(2) .8088(3) .3629(5) .097 Uiso calc PR .92 1 H C7A .38880(14) .9295(3) .4969(5) .1004(13) Uani d PG .92 1 C H71A .4278(5) .918(2) .3927(13) .151 Uiso calc PR .92 1 H H72A .4137(7) .8849(18) .594(3) .151 Uiso calc PR .92 1 H H73A .3904(3) 1.0082(7) .529(4) .151 Uiso calc PR .92 1 H N1B -.0001(8) .9500(11) .475(5) .076(11) Uiso d PD .08 2 N C1B .0954(12) .9019(17) .462(4) .063(6) Uiso d PGD .08 2 C C2B .1811(14) .9538(17) .519(4) .063(6) Uiso d PG .08 2 C H2B .1785(17) 1.016(2) .595(5) .076 Uiso calc PR .08 2 H C3B .2707(12) .9116(18) .463(3) .063(6) Uiso d PG .08 2 C C4B .2746(12) .818(2) .349(4) .063(6) Uiso d PG .08 2 C H4B .3342(13) .790(3) .312(5) .076 Uiso calc PR .08 2 H C5B .1890(14) .766(2) .292(4) .063(6) Uiso d PG .08 2 C H5B .1916(17) .703(3) .217(6) .076 Uiso calc PR .08 2 H C6B .0994(12) .8079(16) .348(4) .063(6) Uiso d PGD .08 2 C H6B .0425(13) .773(2) .311(5) .076 Uiso calc PR .08 2 H C7B .3631(14) .968(3) .524(5) .063(6) Uiso d PG .08 2 C H71B .349(3) 1.018(16) .62(2) .095 Uiso calc PR .08 2 H H72B .391(10) 1.009(18) .427(10) .095 Uiso calc PR .08 2 H H73B .408(7) .911(4) .56(3) .095 Uiso calc PR .08 2 H 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' N N .0061 .0033 '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' 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 N1A N1A C1A 5_576 114.1(3) C2A C1A C6A . 120.0 C2A C1A N1A . 115.2(2) C6A C1A N1A . 124.8(2) C3A C2A C1A . 120.0 C2A C3A C4A . 120.0 C2A C3A C7A . 120.0 C4A C3A C7A . 120.0 C5A C4A C3A . 120.0 C6A C5A C4A . 120.0 C5A C6A C1A . 120.0 N1B N1B C1B 5_576 113.2(12) C6B C1B C2B . 120.0 C6B C1B N1B . 112.9(9) C2B C1B N1B . 125.6(9) C3B C2B C1B . 120.0 C4B C3B C2B . 120.0 C4B C3B C7B . 120.0 C2B C3B C7B . 120.0 C3B C4B C5B . 120.0 C4B C5B C6B . 120.0 C5B C6B C1B . 120.0 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance N1A N1A 5_576 1.245(5) N1A C1A . 1.419(3) C1A C2A . 1.40 C1A C6A . 1.40 C2A C3A . 1.40 C3A C4A . 1.40 C3A C7A . 1.51 C4A C5A . 1.40 C5A C6A . 1.40 N1B N1B 5_576 1.240(11) N1B C1B . 1.439(10) C1B C6B . 1.40 C1B C2B . 1.40 C2B C3B . 1.40 C3B C4B . 1.40 C3B C7B . 1.51 C4B C5B . 1.40 C5B C6B . 1.40 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 N1A N1A C1A C2A 5_576 -176.0(3) N1A N1A C1A C6A 5_576 2.7(4) C6A C1A C2A C3A . .0 N1A C1A C2A C3A . 178.7(2) C1A C2A C3A C4A . .0 C1A C2A C3A C7A . 180.0 C2A C3A C4A C5A . .0 C7A C3A C4A C5A . 180.0 C3A C4A C5A C6A . .0 C4A C5A C6A C1A . .0 C2A C1A C6A C5A . .0 N1A C1A C6A C5A . -178.6(2) N1B N1B C1B C6B 5_576 -159(4) N1B N1B C1B C2B 5_576 7(6) C6B C1B C2B C3B . .0 N1B C1B C2B C3B . -165(3) C1B C2B C3B C4B . .0 C1B C2B C3B C7B . 180.0 C2B C3B C4B C5B . .0 C7B C3B C4B C5B . 180.0 C3B C4B C5B C6B . .0 C4B C5B C6B C1B . .0 C2B C1B C6B C5B . .0 N1B C1B C6B C5B . 167(3) loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 PubChem 11491