#------------------------------------------------------------------------------ #$Date: 2022-09-14 17:38:48 +0100 (Wed, 14 Sep 2022) $ #$Revision: 277834 $ #$URL: svn://www.crystallography.net/cod/cif/2/10/18/2101887.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_2101887 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 'C12 H10 N2' _chemical_formula_sum 'C12 H10 N2' _chemical_formula_weight 182.22 _chemical_melting_point 341 _chemical_name_systematic ' (E)-azobenzene' _space_group_IT_number 14 _space_group_name_Hall '-P 2yab' _space_group_name_H-M_alt 'P 1 21/a 1' _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 112.440(7) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 12.1840(11) _cell_length_b 5.7888(14) _cell_length_c 15.2282(12) _cell_measurement_reflns_used 25 _cell_measurement_temperature 296 _cell_measurement_theta_max 39.7 _cell_measurement_theta_min 34.5 _cell_volume 992.7(3) _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 Cu_K\a _diffrn_radiation_wavelength 1.54184 _diffrn_reflns_av_R_equivalents .0208 _diffrn_reflns_av_sigmaI/netI .0267 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_number 1463 _diffrn_reflns_theta_max 59.94 _diffrn_reflns_theta_min 3.14 _diffrn_standards_decay_% 5 _diffrn_standards_interval_count 150 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu .577 _exptl_absorpt_correction_type none _exptl_crystal_colour red _exptl_crystal_density_diffrn 1.219 _exptl_crystal_description block _exptl_crystal_F_000 384 _exptl_crystal_size_max .40 _exptl_crystal_size_mid .40 _exptl_crystal_size_min .40 _refine_diff_density_max .425 _refine_diff_density_min -.672 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_all 1.185 _refine_ls_goodness_of_fit_obs 1.214 _refine_ls_hydrogen_treatment ; Hydrogen atoms were ridden on the bonded carbon atoms. ; _refine_ls_matrix_type full _refine_ls_number_parameters 145 _refine_ls_number_reflns 1377 _refine_ls_number_restraints 5 _refine_ls_restrained_S_all 1.186 _refine_ls_restrained_S_obs 1.215 _refine_ls_R_factor_all .1080 _refine_ls_R_factor_obs .0953 _refine_ls_shift/esd_max -.046 _refine_ls_shift/esd_mean .005 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.1389P)^2^+0.1181P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_all .2095 _refine_ls_wR_factor_obs .1917 _reflns_number_observed 1124 _reflns_number_total 1377 _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^)+(0.1389P)^2^+0.1181P] 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^)+(0.1389P)^2^+0.1181P] 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 2101887 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 N101 .0481(13) .0402(11) .0498(12) -.0006(9) .0210(10) -.0035(9) C101 .0371(13) .0421(14) .0396(12) .0025(10) .0140(10) .0004(10) C102 .057(2) .0432(15) .055(2) -.0011(13) .0231(13) -.0056(12) C103 .067(2) .049(2) .057(2) .0062(14) .0263(14) -.0103(13) C104 .060(2) .063(2) .0503(14) .0103(14) .0303(14) .0017(13) C105 .051(2) .057(2) .053(2) -.0034(14) .0227(13) .0026(13) C106 .0447(15) .0430(14) .0440(14) .0006(11) .0170(11) -.0021(11) N201A .053(2) .054(2) .052(2) -.0048(13) .0148(14) -.0092(12) C201A .053(2) .049(2) .042(2) -.003(2) .019(2) -.002(2) C202A .051(2) .063(2) .060(2) -.011(2) .019(2) -.014(2) C203A .050(3) .078(3) .055(2) -.007(2) .014(2) -.011(2) C204A .055(2) .071(3) .048(2) .001(2) .014(2) .001(2) C205A .060(2) .072(3) .052(2) .002(2) .016(2) -.003(2) C206A .054(2) .062(2) .046(2) .000(2) .014(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_refinement_flags _atom_site_occupancy _atom_site_disorder_group _atom_site_type_symbol N101 .0035(2) -.1022(4) -.5116(2) .0454(6) Uani d . 1 . N C101 .0735(2) -.1341(4) -.5674(2) .0398(7) Uani d . 1 . C C102 .0597(3) -.3441(5) -.6143(2) .0514(8) Uani d . 1 . C C103 .1225(3) -.3892(5) -.6709(2) .0570(8) Uani d . 1 . C C104 .2026(3) -.2292(5) -.6781(2) .0549(8) Uani d . 1 . C C105 .2188(2) -.0226(5) -.6287(2) .0529(8) Uani d . 1 . C C106 .1541(2) .0277(4) -.5740(2) .0439(7) Uani d . 1 . C H102 .005(3) -.456(7) -.606(2) .072(9) Uiso d . 1 . H H103 .109(3) -.528(7) -.706(3) .086(11) Uiso d . 1 . H H104 .247(3) -.251(5) -.716(2) .055(8) Uiso d . 1 . H H105 .277(3) .090(5) -.631(2) .056(8) Uiso d . 1 . H H106 .163(3) .163(6) -.537(2) .057(8) Uiso d . 1 . H N201A -.4773(2) .0756(5) -.9695(2) .0543(8) Uani d PD .81 1 N C201A -.35277(14) .0548(5) -.9205(2) .0476(9) Uani d PGD .81 1 C C202A -.2966(2) .2370(4) -.8594(2) .0584(11) Uani d PGD .81 1 C H202A -.3408(3) .3624(6) -.8533(3) .070 Uiso calc PR .81 1 H C203A -.1739(2) .2303(5) -.8075(2) .0625(12) Uani d PG .81 1 C H203A -.1366(3) .3513(7) -.7670(3) .075 Uiso calc PR .81 1 H C204A -.10728(15) .0414(6) -.8168(3) .0599(12) Uani d PG .81 1 C H204A -.0257(2) .0370(9) -.7823(4) .072 Uiso calc PR .81 1 H C205A -.1634(2) -.1408(5) -.8778(3) .0631(12) Uani d PG .81 1 C H205A -.1192(3) -.2662(7) -.8840(4) .076 Uiso calc PR .81 1 H C206A -.2862(2) -.1341(4) -.9297(2) .0555(10) Uani d PG .81 1 C H206A -.3235(3) -.2551(6) -.9703(3) .067 Uiso calc PR .81 1 H N201B -.4619(6) -.0768(16) -.9940(9) .055(3) Uiso d PD .19 2 N C201B -.3469(6) -.015(3) -.9294(12) .055(3) Uiso d PGD .19 2 C C202B -.3250(12) .195(2) -.8797(12) .055(3) Uiso d PG .19 2 C H202B -.3876(16) .294(3) -.8855(18) .066 Uiso calc PR .19 2 H C203B -.2088(15) .256(2) -.8212(13) .055(3) Uiso d PG .19 2 C H203B -.194(2) .395(3) -.7881(18) .066 Uiso calc PR .19 2 H C204B -.1145(10) .107(3) -.8124(14) .055(3) Uiso d PG .19 2 C H204B -.0373(12) .148(4) -.774(2) .066 Uiso calc PR .19 2 H C205B -.1364(6) -.102(3) -.8622(15) .055(3) Uiso d PG .19 2 C H205B -.0737(9) -.201(4) -.856(2) .066 Uiso calc PR .19 2 H C206B -.2526(8) -.163(2) -.9207(13) .055(3) Uiso d PGD .19 2 C H206B -.2672(14) -.302(3) -.9537(18) .066 Uiso calc PR .19 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 .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 N101 N101 C101 3_554 114.4(3) C106 C101 C102 . 120.3(2) C106 C101 N101 . 123.8(2) C102 C101 N101 . 115.9(2) C103 C102 C101 . 120.1(3) C102 C103 C104 . 120.0(3) C103 C104 C105 . 119.7(3) C106 C105 C104 . 120.9(3) C105 C106 C101 . 119.0(3) N201A N201A C201A 3_453 114.5(4) C202A C201A C206A . 120.0 C202A C201A N201A . 116.0(2) C206A C201A N201A . 124.0(2) C201A C202A C203A . 120.0 C202A C203A C204A . 120.0 C205A C204A C203A . 120.0 C204A C205A C206A . 120.0 C205A C206A C201A . 120.0 N201B N201B C201B 3_453 113.8(11) C202B C201B C206B . 120.0 C202B C201B N201B . 122.0(8) C206B C201B N201B . 117.9(9) C201B C202B C203B . 120.0 C204B C203B C202B . 120.0 C203B C204B C205B . 120.0 C204B C205B C206B . 120.0 C205B C206B C201B . 120.0 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance N101 N101 3_554 1.247(4) N101 C101 . 1.427(3) C101 C106 . 1.388(4) C101 C102 . 1.387(4) C102 C103 . 1.378(4) C103 C104 . 1.380(5) C104 C105 . 1.386(4) C105 C106 . 1.380(4) N201A N201A 3_453 1.243(5) N201A C201A . 1.417(3) C201A C202A . 1.40 C201A C206A . 1.40 C202A C203A . 1.40 C203A C204A . 1.40 C204A C205A . 1.40 C205A C206A . 1.40 N201B N201B 3_453 1.247(10) N201B C201B . 1.417(9) C201B C202B . 1.40 C201B C206B . 1.40 C202B C203B . 1.40 C203B C204B . 1.40 C204B C205B . 1.40 C205B C206B . 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 N101 N101 C101 C106 3_554 17.4(4) N101 N101 C101 C102 3_554 -164.4(3) C106 C101 C102 C103 . -2.6(4) N101 C101 C102 C103 . 179.1(2) C101 C102 C103 C104 . 2.4(4) C102 C103 C104 C105 . -.4(4) C103 C104 C105 C106 . -1.4(4) C104 C105 C106 C101 . 1.2(4) C102 C101 C106 C105 . .8(4) N101 C101 C106 C105 . 178.9(2) N201A N201A C201A C202A 3_453 172.7(3) N201A N201A C201A C206A 3_453 -7.8(5) C206A C201A C202A C203A . .0 N201A C201A C202A C203A . 179.5(3) C201A C202A C203A C204A . .0 C202A C203A C204A C205A . .0 C203A C204A C205A C206A . .0 C204A C205A C206A C201A . .0 C202A C201A C206A C205A . .0 N201A C201A C206A C205A . -179.5(3) N201B N201B C201B C202B 3_453 4(3) N201B N201B C201B C206B 3_453 -171.9(16) C206B C201B C202B C203B . .0 N201B C201B C202B C203B . -175.9(18) C201B C202B C203B C204B . .0 C202B C203B C204B C205B . .0 C203B C204B C205B C206B . .0 C204B C205B C206B C201B . .0 C202B C201B C206B C205B . .0 N201B C201B C206B C205B . 176.1(17)