#------------------------------------------------------------------------------ #$Date: 2025-08-19 11:01:59 +0100 (Tue, 19 Aug 2025) $ #$Revision: 301802 $ #$URL: svn://www.crystallography.net/cod/cif/2/10/18/2101896.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_2101896 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_name_systematic ' (E)-4,4'-dimethylazobenzene' _space_group_IT_number 14 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2yab' _symmetry_space_group_name_H-M 'P 1 21/a 1' _audit_creation_method SHELXL _cell_angle_alpha 90.00 _cell_angle_beta 89.654(9) _cell_angle_gamma 90.00 _cell_formula_units_Z 2 _cell_length_a 11.9762(12) _cell_length_b 4.8462(5) _cell_length_c 9.7193(10) _cell_measurement_reflns_used 25 _cell_measurement_temperature 296 _cell_measurement_theta_max 14.8 _cell_measurement_theta_min 13.9 _cell_volume 564.09(10) _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 'SHELXS-86 (Sheldrick, 1990)' _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 .0302 _diffrn_reflns_av_sigmaI/netI .0483 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 0 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_number 1733 _diffrn_reflns_theta_max 30.00 _diffrn_reflns_theta_min 2.10 _diffrn_standards_decay_% 3 _diffrn_standards_interval_count 150 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu .074 _exptl_absorpt_correction_type none _exptl_crystal_colour orange _exptl_crystal_density_diffrn 1.238 _exptl_crystal_description block _exptl_crystal_F_000 224 _exptl_crystal_size_max .40 _exptl_crystal_size_mid .40 _exptl_crystal_size_min .35 _refine_diff_density_max .322 _refine_diff_density_min -.406 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_all 1.047 _refine_ls_goodness_of_fit_obs 1.140 _refine_ls_hydrogen_treatment ; Hydrogen atoms were ridden on the bonded carbon atoms. ; _refine_ls_matrix_type full _refine_ls_number_parameters 117 _refine_ls_number_reflns 1646 _refine_ls_number_restraints 5 _refine_ls_restrained_S_all 1.045 _refine_ls_restrained_S_obs 1.138 _refine_ls_R_factor_all .1100 _refine_ls_R_factor_obs .0665 _refine_ls_shift/esd_max .269 _refine_ls_shift/esd_mean .023 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.1136P)^2^+0.0257P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_all .1971 _refine_ls_wR_factor_obs .1678 _reflns_number_observed 1042 _reflns_number_total 1646 _reflns_observed_criterion >2sigma(I) _cod_data_source_file oa0007.cif _cod_data_source_block 4296 _cod_depositor_comments ; The following automatic conversions were performed: '_refine_ls_weighting_scheme' value 'calc w=1/[\s^2^(Fo^2^)+(0.1136P)^2^+0.0257P] 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^)+(0.1136P)^2^+0.0257P] 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 2101896 _cod_database_fobs_code 2101896 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z' '-x, -y, -z' 'x-1/2, -y-1/2, z' 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 .037(2) .0370(14) .0345(13) -.0036(11) .0031(11) .0000(11) C1A .029(2) .0315(14) .0291(15) .001(2) .0002(14) -.0006(11) C2A .028(2) .045(2) .041(2) .000(2) -.0014(15) .0021(14) C3A .039(2) .043(2) .049(2) -.007(2) .003(2) .004(2) C4A .032(2) .027(4) .042(4) -.008(2) .013(2) -.003(3) C5A .031(2) .039(2) .0329(15) .0014(15) -.0058(13) .0020(14) C6A .024(2) .046(2) .034(2) -.007(2) -.0039(14) .001(2) C7A .068(4) .029(3) .056(4) -.005(3) .012(3) .000(3) N1B .044(2) .038(2) .0339(15) .0001(14) .0019(14) .0027(13) C1B .033(2) .032(2) .028(2) .001(2) -.002(2) -.0008(14) C2B .028(2) .043(2) .031(2) .007(2) -.007(2) .0058(14) C3B .027(2) .037(2) .039(2) -.0016(15) .0003(14) -.004(2) C4B .061(5) .032(5) .026(4) .016(3) -.002(3) -.001(3) C5B .053(3) .049(3) .041(2) .002(2) -.001(2) .014(2) C6B .036(2) .045(2) .034(2) .000(2) -.010(2) .006(2) C7B .051(3) .046(5) .034(3) .004(3) .012(2) .010(3) 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 .0480(2) -.4492(6) .9988(3) .0362(6) Uani d PD .54 1 N C1A .0654(2) -.2449(6) .8953(3) .0300(7) Uani d PGD .54 1 C C2A .1739(2) -.1384(9) .8868(4) .0379(9) Uani d PGD .54 1 C H2A .2284(3) -.1997(13) .9473(6) .046 Uiso calc PR .54 1 H C3A .2003(3) .0602(10) .7872(5) .0437(12) Uani d PG .54 1 C H3A .2723(3) .1309(14) .7816(7) .052 Uiso calc PR .54 1 H C4A .1182(4) .1523(8) .6961(4) .034(2) Uani d PG .54 1 C C5A .0097(3) .0459(9) .7046(4) .0343(8) Uani d PG .54 1 C H5A -.0448(4) .1072(12) .6441(5) .041 Uiso calc PR .54 1 H C6A -.0167(2) -.1527(8) .8042(4) .0345(9) Uani d PG .54 1 C H6A -.0888(2) -.2234(12) .8098(5) .041 Uiso calc PR .54 1 H C7A .1467(6) .3666(12) .5887(6) .051(2) Uani d PG .54 1 C H71A .139(3) .5475(11) .6278(13) .076 Uiso calc PR .54 1 H H72A .097(2) .348(5) .5121(17) .076 Uiso calc PR .54 1 H H73A .2223(11) .340(5) .558(3) .076 Uiso calc PR .54 1 H N1B -.0310(3) -.4439(7) .9566(3) .0385(7) Uani d PD .46 2 N C1B .0234(3) -.2399(7) .8730(3) .0309(8) Uani d PGD .46 2 C C2B .1353(3) -.1602(10) .8841(4) .0338(10) Uani d PG .46 2 C H2B .1802(3) -.2382(14) .9514(6) .041 Uiso calc PR .46 2 H C3B .1796(3) .0371(11) .7938(5) .0347(10) Uani d PG .46 2 C H3B .2540(3) .0901(16) .8012(7) .042 Uiso calc PR .46 2 H C4B .1120(5) .1547(10) .6925(4) .040(3) Uani d PG .46 2 C C5B .0001(4) .0749(12) .6814(5) .0478(15) Uani d PG .46 2 C H5B -.0448(6) .1530(16) .6141(6) .057 Uiso calc PR .46 2 H C6B -.0442(3) -.1224(11) .7716(4) .0382(10) Uani d PGD .46 2 C H6B -.1186(3) -.1754(15) .7643(6) .046 Uiso calc PR .46 2 H C7B .1598(7) .3675(15) .5951(7) .044(2) Uani d PG .46 2 C H71B .1086(16) .519(4) .587(3) .065 Uiso calc PR .46 2 H H72B .172(3) .285(3) .5063(12) .065 Uiso calc PR .46 2 H H73B .2297(17) .434(6) .630(2) .065 Uiso calc PR .46 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 3_547 114.6(4) C2A C1A C6A . 120.0 C2A C1A N1A . 115.4(2) C6A C1A N1A . 124.6(2) C3A C2A C1A . 120.0 C2A C3A C4A . 120.0 C3A C4A C5A . 120.0 C3A C4A C7A . 120.0 C5A C4A C7A . 120.0 C6A C5A C4A . 120.0 C5A C6A C1A . 120.0 N1B N1B C1B 3_547 114.3(5) C6B C1B C2B . 120.0 C6B C1B N1B . 114.6(3) C2B C1B N1B . 125.4(3) C1B C2B C3B . 120.0 C4B C3B C2B . 120.0 C3B C4B C5B . 120.0 C3B C4B C7B . 120.0 C5B C4B C7B . 120.0 C6B C5B C4B . 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 3_547 1.251(4) N1A C1A . 1.426(4) C1A C2A . 1.40 C1A C6A . 1.40 C2A C3A . 1.40 C3A C4A . 1.40 C4A C5A . 1.40 C4A C7A . 1.51 C5A C6A . 1.40 N1B N1B 3_547 1.252(5) N1B C1B . 1.434(4) C1B C6B . 1.40 C1B C2B . 1.40 C2B C3B . 1.40 C3B C4B . 1.40 C4B C5B . 1.40 C4B C7B . 1.51 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 3_547 -177.1(3) N1A N1A C1A C6A 3_547 1.8(5) C6A C1A C2A C3A . .0 N1A C1A C2A C3A . 179.0(3) C1A C2A C3A C4A . .0 C2A C3A C4A C5A . .0 C2A C3A C4A C7A . -180.0 C3A C4A C5A C6A . .0 C7A C4A C5A C6A . 180.0 C4A C5A C6A C1A . .0 C2A C1A C6A C5A . .0 N1A C1A C6A C5A . -178.9(3) N1B N1B C1B C6B 3_547 177.3(4) N1B N1B C1B C2B 3_547 -1.1(6) C6B C1B C2B C3B . .0 N1B C1B C2B C3B . 178.4(4) C1B C2B C3B C4B . .0 C2B C3B C4B C5B . .0 C2B C3B C4B C7B . 180.0 C3B C4B C5B C6B . .0 C7B C4B C5B C6B . 180.0 C4B C5B C6B C1B . .0 C2B C1B C6B C5B . .0 N1B C1B C6B C5B . -178.5(3) loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 PubChem 10389