#------------------------------------------------------------------------------ #$Date: 2013-08-29 18:37:19 +0300 (Thu, 29 Aug 2013) $ #$Revision: 88064 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/22/27/2222773.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_2222773 loop_ _publ_author_name 'Golovnia, Ekaterina' 'Prisyazhnaya, Elena V.' 'Iskenderov, Turganbay S.' 'Haukka, Matti' 'Fritsky, Igor O.' _publ_section_title ; 2,2'-Dihydroxybiphenyl-3,3'-dicarbaldehyde dioxime ; _journal_coeditor_code JH2095 _journal_issue 8 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o2018 _journal_page_last o2019 _journal_volume 65 _journal_year 2009 _chemical_formula_iupac 'C14 H12 N2 O4' _chemical_formula_moiety 'C14 H12 N2 O4' _chemical_formula_sum 'C14 H12 N2 O4' _chemical_formula_weight 272.26 _chemical_name_systematic ; 2,2'-Dihydroxy-1,1'-biphenyl-3,3'-dicarbaldehyde dioxime ; _space_group_IT_number 15 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-C 2yc' _symmetry_space_group_name_H-M 'C 1 2/c 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-97 _cell_angle_alpha 90.00 _cell_angle_beta 129.652(6) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 24.2780(14) _cell_length_b 3.9279(4) _cell_length_c 16.6466(12) _cell_measurement_reflns_used 516 _cell_measurement_temperature 120(2) _cell_measurement_theta_max 27.00 _cell_measurement_theta_min 4.50 _cell_volume 1222.2(2) _computing_cell_refinement 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _computing_data_collection 'COLLECT (Bruker--Nonius, 2004)' _computing_data_reduction 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _computing_molecular_graphics 'DIAMOND (Brandenburg, 2006)' _computing_publication_material 'SHELXL97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)' _computing_structure_solution 'SHELXS97 (Sheldrick, 2008)' _diffrn_ambient_temperature 120(2) _diffrn_detector_area_resol_mean 9 _diffrn_measured_fraction_theta_full 0.996 _diffrn_measured_fraction_theta_max 0.993 _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_method '\f scans and \w scans with \k offset' _diffrn_radiation_monochromator 'horizontally mounted graphite crystal' _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0733 _diffrn_reflns_av_sigmaI/netI 0.0864 _diffrn_reflns_limit_h_max 30 _diffrn_reflns_limit_h_min -30 _diffrn_reflns_limit_k_max 4 _diffrn_reflns_limit_k_min -5 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_number 4331 _diffrn_reflns_theta_full 25.00 _diffrn_reflns_theta_max 27.52 _diffrn_reflns_theta_min 4.36 _exptl_absorpt_coefficient_mu 0.111 _exptl_absorpt_correction_T_max 0.9929 _exptl_absorpt_correction_T_min 0.9756 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SADABS; Sheldrick, 2001)' _exptl_crystal_colour pale-yellow _exptl_crystal_density_diffrn 1.480 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 568 _exptl_crystal_size_max 0.19 _exptl_crystal_size_mid 0.09 _exptl_crystal_size_min 0.06 _refine_diff_density_max 0.272 _refine_diff_density_min -0.294 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.017 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 99 _refine_ls_number_reflns 1388 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.017 _refine_ls_R_factor_all 0.1123 _refine_ls_R_factor_gt 0.0558 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0673P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1210 _refine_ls_wR_factor_ref 0.1457 _reflns_number_gt 812 _reflns_number_total 1388 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file jh2095.cif _[local]_cod_data_source_block I _[local]_cod_cif_authors_sg_H-M 'C 2/c' _cod_database_code 2222773 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _atom_site_type_symbol _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 O O1 0.50535(8) 0.1656(4) 0.11701(11) 0.0286(5) Uani d . 1 . . O O2 0.64023(9) -0.1055(4) 0.07166(13) 0.0350(5) Uani d . 1 . . N N1 0.60748(10) 0.0232(5) 0.11062(14) 0.0279(5) Uani d . 1 . . C C1 0.55751(12) 0.2918(5) 0.21487(16) 0.0236(6) Uani d . 1 . . C C2 0.53803(11) 0.4208(6) 0.27199(16) 0.0235(6) Uani d . 1 . . C C3 0.59205(12) 0.5499(6) 0.37151(16) 0.0265(6) Uani d . 1 . . H H3 0.5795 0.6439 0.4105 0.032 Uiso calc R 1 . . C C4 0.66275(12) 0.5455(6) 0.41490(17) 0.0269(6) Uani d . 1 . . H H4 0.6983 0.6329 0.4832 0.032 Uiso calc R 1 . . C C5 0.68185(12) 0.4140(6) 0.35911(16) 0.0272(6) Uani d . 1 . . H H5 0.7308 0.4102 0.3893 0.033 Uiso calc R 1 . . C C6 0.62978(11) 0.2855(6) 0.25813(16) 0.0237(6) Uani d . 1 . . C C7 0.65242(12) 0.1435(6) 0.20269(17) 0.0265(6) Uani d . 1 . . H H7 0.7019 0.1402 0.2358 0.032 Uiso calc R 1 . . H H1 0.5270(14) 0.081(7) 0.0923(19) 0.042(8) Uiso d . 1 . . H H2 0.5979(18) -0.165(8) -0.002(3) 0.067(9) Uiso d . 1 . . 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 O1 0.0229(9) 0.0387(10) 0.0217(9) -0.0034(7) 0.0132(8) -0.0059(7) O2 0.0324(10) 0.0468(11) 0.0296(10) 0.0008(8) 0.0217(9) -0.0042(8) N1 0.0299(11) 0.0321(11) 0.0277(11) 0.0015(9) 0.0212(10) -0.0001(8) C1 0.0244(13) 0.0233(12) 0.0192(12) -0.0006(9) 0.0121(11) 0.0013(9) C2 0.0235(12) 0.0218(12) 0.0213(11) -0.0002(9) 0.0124(11) 0.0017(9) C3 0.0306(14) 0.0266(13) 0.0231(12) -0.0015(10) 0.0176(11) 0.0000(10) C4 0.0253(13) 0.0301(13) 0.0178(11) -0.0044(10) 0.0103(10) -0.0024(9) C5 0.0211(12) 0.0290(14) 0.0257(12) -0.0018(10) 0.0123(11) 0.0011(10) C6 0.0237(13) 0.0246(12) 0.0204(12) -0.0012(9) 0.0130(11) 0.0020(9) C7 0.0207(12) 0.0311(13) 0.0252(12) -0.0008(10) 0.0136(11) 0.0008(10) 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 O1 C1 . 1.368(3) ? O1 H1 . 0.91(3) ? O2 N1 . 1.402(2) ? O2 H2 . 1.00(3) ? N1 C7 . 1.276(3) ? C1 C2 . 1.399(3) ? C1 C6 . 1.409(3) ? C2 C3 . 1.396(3) ? C2 C2 2_655 1.490(4) ? C3 C4 . 1.373(3) ? C3 H3 . 0.9500 ? C4 C5 . 1.376(3) ? C4 H4 . 0.9500 ? C5 C6 . 1.402(3) ? C5 H5 . 0.9500 ? C6 C7 . 1.453(3) ? C7 H7 . 0.9500 ? 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_site_symmetry_3 _geom_angle _geom_angle_publ_flag C1 O1 H1 . . 107.9(16) ? N1 O2 H2 . . 101.8(18) ? C7 N1 O2 . . 112.73(17) ? O1 C1 C2 . . 118.89(19) ? O1 C1 C6 . . 120.46(19) ? C2 C1 C6 . . 120.6(2) ? C3 C2 C1 . . 118.0(2) ? C3 C2 C2 . 2_655 120.9(2) ? C1 C2 C2 . 2_655 121.1(2) ? C4 C3 C2 . . 122.1(2) ? C4 C3 H3 . . 118.9 ? C2 C3 H3 . . 118.9 ? C3 C4 C5 . . 119.7(2) ? C3 C4 H4 . . 120.1 ? C5 C4 H4 . . 120.1 ? C4 C5 C6 . . 120.7(2) ? C4 C5 H5 . . 119.7 ? C6 C5 H5 . . 119.7 ? C5 C6 C1 . . 118.83(19) ? C5 C6 C7 . . 118.8(2) ? C1 C6 C7 . . 122.31(19) ? N1 C7 C6 . . 121.6(2) ? N1 C7 H7 . . 119.2 ? C6 C7 H7 . . 119.2 ? 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_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion _geom_torsion_publ_flag O1 C1 C2 C3 . . . . -179.69(18) ? C6 C1 C2 C3 . . . . 1.6(3) ? O1 C1 C2 C2 . . . 2_655 0.3(3) ? C6 C1 C2 C2 . . . 2_655 -178.47(16) ? C1 C2 C3 C4 . . . . -1.7(3) ? C2 C2 C3 C4 2_655 . . . 178.39(17) ? C2 C3 C4 C5 . . . . 0.8(3) ? C3 C4 C5 C6 . . . . 0.3(3) ? C4 C5 C6 C1 . . . . -0.3(3) ? C4 C5 C6 C7 . . . . -178.9(2) ? O1 C1 C6 C5 . . . . -179.3(2) ? C2 C1 C6 C5 . . . . -0.6(3) ? O1 C1 C6 C7 . . . . -0.8(3) ? C2 C1 C6 C7 . . . . 177.9(2) ? O2 N1 C7 C6 . . . . -179.16(18) ? C5 C6 C7 N1 . . . . -179.9(2) ? C1 C6 C7 N1 . . . . 1.5(3) ? 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 O1 H1 N1 . 0.91(3) 1.79(3) 2.609(2) 148(2) O2 H2 O1 5_655 1.00(3) 1.96(3) 2.871(2) 151(3) _cod_database_fobs_code 2222773