#------------------------------------------------------------------------------ #$Date: 2025-08-19 11:01:59 +0100 (Tue, 19 Aug 2025) $ #$Revision: 301802 $ #$URL: svn://www.crystallography.net/cod/cif/2/10/18/2101894.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_2101894 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 _chemical_name_systematic ' (E)-3,3'-dimethylazobenzene' _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 4 _cell_length_a 13.824(2) _cell_length_b 11.731(2) _cell_length_c 7.366(2) _cell_measurement_reflns_used 25 _cell_measurement_temperature 200 _cell_measurement_theta_max 39.9 _cell_measurement_theta_min 38.0 _cell_volume 1194.5(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 200 _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 Cu_K\a _diffrn_radiation_wavelength 1.54184 _diffrn_reflns_av_R_equivalents .0000 _diffrn_reflns_av_sigmaI/netI .0137 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 0 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_number 738 _diffrn_reflns_theta_max 59.82 _diffrn_reflns_theta_min 6.40 _diffrn_standards_decay_% 0 _diffrn_standards_interval_count 150 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu .540 _exptl_absorpt_correction_type none _exptl_crystal_colour red _exptl_crystal_density_diffrn 1.169 _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 .376 _refine_diff_density_min -.566 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_all 1.220 _refine_ls_goodness_of_fit_obs 1.280 _refine_ls_hydrogen_treatment refall _refine_ls_matrix_type full _refine_ls_number_parameters 101 _refine_ls_number_reflns 738 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.220 _refine_ls_restrained_S_obs 1.280 _refine_ls_R_factor_all .0727 _refine_ls_R_factor_obs .0645 _refine_ls_shift/esd_max -.073 _refine_ls_shift/esd_mean .005 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0930P)^2^+0.2183P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_all .1572 _refine_ls_wR_factor_obs .1509 _reflns_number_observed 634 _reflns_number_total 738 _reflns_observed_criterion >2sigma(I) _cod_data_source_file oa0007.cif _cod_data_source_block 3200 _cod_depositor_comments ; The following automatic conversions were performed: '_refine_ls_weighting_scheme' value 'calc w=1/[\s^2^(Fo^2^)+(0.0930P)^2^+0.2183P] 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^)+(0.0930P)^2^+0.2183P] 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 2101894 _cod_database_fobs_code 2101894 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 N1 .0588(13) .0415(13) .0448(12) -.0014(10) -.0024(9) .0007(8) C1 .059(2) .0374(14) .0383(13) .0031(11) .0002(10) .0028(10) C2 .060(2) .0379(15) .0397(14) -.0035(12) .0044(10) -.0003(10) C3 .060(2) .047(2) .0396(13) .0007(12) .0070(10) .0052(11) C4 .068(2) .050(2) .0436(14) .0108(13) .0049(12) -.0013(11) C5 .081(2) .0426(14) .0481(14) .0040(13) -.0040(12) -.0087(11) C6 .064(2) .0440(14) .048(2) .0001(12) -.0089(12) -.0028(11) C7 .056(2) .070(2) .073(2) -.004(2) .011(2) -.003(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_occupancy _atom_site_type_symbol N1 .04227(14) 1.0171(2) .5106(2) .0484(7) Uani d 1 N C1 .1148(2) .9348(2) .4629(3) .0450(7) Uani d 1 C C2 .2097(2) .9676(2) .4986(3) .0458(8) Uani d 1 C C3 .2867(2) .8957(2) .4607(3) .0487(8) Uani d 1 C C4 .2662(2) .7903(2) .3848(3) .0539(8) Uani d 1 C C5 .1721(2) .7571(2) .3488(3) .0571(8) Uani d 1 C C6 .0954(2) .8286(2) .3865(3) .0519(8) Uani d 1 C C7 .3887(2) .9312(3) .4990(5) .0664(10) Uani d 1 C H2 .2210(16) 1.044(2) .555(3) .044(6) Uiso d 1 H H4 .3212(18) .738(2) .351(4) .057(7) Uiso d 1 H H5 .1588(16) .681(2) .296(4) .064(8) Uiso d 1 H H6 .0262(19) .805(2) .371(3) .060(7) Uiso d 1 H H71 .428(3) .918(4) .411(6) .129(15) Uiso d 1 H H72 .420(3) .888(4) .588(6) .135(16) Uiso d 1 H H73 .392(3) 1.005(5) .540(7) .16(2) 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 C C .0181 .0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N .0311 .0180 '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 N1 N1 C1 5_576 114.0(2) C2 C1 C6 . 120.3(2) C2 C1 N1 . 115.2(2) C6 C1 N1 . 124.5(2) C3 C2 C1 . 121.2(2) C3 C2 H2 . 120.5(13) C1 C2 H2 . 118.3(13) C4 C3 C2 . 117.8(2) C4 C3 C7 . 121.1(2) C2 C3 C7 . 121.1(2) C5 C4 C3 . 121.4(2) C5 C4 H4 . 119.2(14) C3 C4 H4 . 119.3(14) C6 C5 C4 . 120.8(2) C6 C5 H5 . 118.9(14) C4 C5 H5 . 120.2(14) C5 C6 C1 . 118.5(2) C5 C6 H6 . 122.6(14) C1 C6 H6 . 118.7(14) C3 C7 H71 . 113(3) C3 C7 H72 . 115(3) H71 C7 H72 . 98(4) C3 C7 H73 . 112(3) H71 C7 H73 . 113(4) H72 C7 H73 . 105(4) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance N1 N1 5_576 1.246(4) N1 C1 . 1.436(3) C1 C2 . 1.392(3) C1 C6 . 1.392(3) C2 C3 . 1.387(3) C2 H2 . 1.00(2) C3 C4 . 1.387(4) C3 C7 . 1.497(4) C4 C5 . 1.383(4) C4 H4 . 1.01(3) C5 C6 . 1.380(4) C5 H5 . .99(3) C6 H6 . 1.00(3) C7 H71 . .86(4) C7 H72 . .93(5) C7 H73 . .92(6) 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 N1 N1 C1 C2 5_576 -175.2(2) N1 N1 C1 C6 5_576 4.7(4) C6 C1 C2 C3 . -.5(4) N1 C1 C2 C3 . 179.4(2) C1 C2 C3 C4 . .4(4) C1 C2 C3 C7 . 179.9(2) C2 C3 C4 C5 . -.3(4) C7 C3 C4 C5 . -179.8(3) C3 C4 C5 C6 . .3(4) C4 C5 C6 C1 . -.4(4) C2 C1 C6 C5 . .5(4) N1 C1 C6 C5 . -179.4(2) loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 PubChem 11491