#------------------------------------------------------------------------------ #$Date: 2017-10-13 11:03:29 +0300 (Fri, 13 Oct 2017) $ #$Revision: 201974 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/21/60/2216056.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_2216056 loop_ _publ_author_name 'G\"ul, Zarife Sibel' 'Er\,sahin, Ferda' 'A\(gar, Erbil' 'I\,s\?ik, \,Samil' _publ_section_title ; (E)-4-Bromo-2-(2-methoxyphenyliminomethyl)phenol ; _journal_coeditor_code LW2037 _journal_issue 11 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o4241 _journal_page_last o4241 _journal_paper_doi 10.1107/S1600536807047824 _journal_volume 63 _journal_year 2007 _chemical_formula_iupac 'C14 H12 Br N O2' _chemical_formula_moiety 'C14 H12 Br N O2' _chemical_formula_sum 'C14 H12 Br N O2' _chemical_formula_weight 306.16 _chemical_name_systematic ; (E)-4-Bromo-2-(2-methoxyphenyliminomethyl)phenol ; _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 SHELXL97 _cell_angle_alpha 90.00 _cell_angle_beta 108.465(7) _cell_angle_gamma 90.00 _cell_formula_units_Z 8 _cell_length_a 32.926(3) _cell_length_b 4.5564(2) _cell_length_c 17.7214(16) _cell_measurement_reflns_used 12164 _cell_measurement_temperature 296 _cell_measurement_theta_max 29.49 _cell_measurement_theta_min 2.36 _cell_volume 2521.8(4) _computing_cell_refinement 'X-AREA (Stoe & Cie, 2002)' _computing_data_collection 'X-AREA (Stoe & Cie, 2002)' _computing_data_reduction 'X-RED32 (Stoe & Cie, 2002)' _computing_molecular_graphics 'ORTEP-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX (Farrugia, 1999)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _diffrn_ambient_temperature 296 _diffrn_detector_area_resol_mean 6.67 _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 1.000 _diffrn_measurement_device_type 'Stoe IPDS II' _diffrn_measurement_method \w _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0518 _diffrn_reflns_av_sigmaI/netI 0.0328 _diffrn_reflns_limit_h_max 40 _diffrn_reflns_limit_h_min -40 _diffrn_reflns_limit_k_max 5 _diffrn_reflns_limit_k_min -5 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_number 12218 _diffrn_reflns_theta_full 26.00 _diffrn_reflns_theta_max 26.00 _diffrn_reflns_theta_min 2.36 _diffrn_standards_decay_% <2 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 3.253 _exptl_absorpt_correction_T_max 0.7122 _exptl_absorpt_correction_T_min 0.2210 _exptl_absorpt_correction_type integration _exptl_absorpt_process_details '(X-RED32; Stoe & Cie, 2002)' _exptl_crystal_colour brown _exptl_crystal_density_diffrn 1.613 _exptl_crystal_density_method 'not measured' _exptl_crystal_description prism _exptl_crystal_F_000 1232 _exptl_crystal_size_max 0.80 _exptl_crystal_size_mid 0.38 _exptl_crystal_size_min 0.08 _refine_diff_density_max 0.260 _refine_diff_density_min -0.455 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 0.977 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 163 _refine_ls_number_reflns 2480 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 0.977 _refine_ls_R_factor_all 0.0564 _refine_ls_R_factor_gt 0.0321 _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^)+(0.0418P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0703 _refine_ls_wR_factor_ref 0.0779 _reflns_number_gt 1712 _reflns_number_total 2480 _reflns_threshold_expression I>2\s(I) _cod_data_source_file lw2037.cif _cod_data_source_block I _cod_original_sg_symbol_H-M 'C 2/c' _cod_database_code 2216056 _cod_database_fobs_code 2216056 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_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 Br Br1 0.234247(8) -0.00729(8) 0.138938(19) 0.06755(13) Uani d . 1 O O2 0.41248(5) 0.4833(4) 0.22498(11) 0.0609(5) Uani d . 1 H H2 0.4147 0.5989 0.1910 0.091 Uiso calc R 1 N N1 0.38806(6) 0.7855(4) 0.09558(12) 0.0442(5) Uani d . 1 C C1 0.29059(8) 0.1497(6) 0.16474(16) 0.0456(6) Uani d . 1 C C8 0.39867(7) 0.9886(6) 0.04460(14) 0.0421(5) Uani d . 1 C C9 0.37013(8) 1.1040(6) -0.02393(16) 0.0492(6) Uani d . 1 H H9 0.3415 1.0472 -0.0391 0.059 Uiso calc R 1 O O1 0.46804(6) 0.9510(5) 0.13433(11) 0.0636(6) Uani d . 1 C C3 0.34117(7) 0.4621(5) 0.13301(14) 0.0401(5) Uani d . 1 C C4 0.37255(7) 0.3770(6) 0.20377(15) 0.0440(6) Uani d . 1 C C10 0.38344(9) 1.3026(6) -0.07027(16) 0.0533(7) Uani d . 1 H H10 0.3640 1.3775 -0.1165 0.064 Uiso calc R 1 C C2 0.30006(7) 0.3460(6) 0.11415(15) 0.0453(6) Uani d . 1 H H22 0.2791 0.4014 0.0674 0.054 Uiso calc R 1 C C7 0.35084(8) 0.6732(6) 0.07962(15) 0.0453(6) Uani d . 1 H H7 0.3296 0.7271 0.0331 0.054 Uiso calc R 1 C C5 0.36185(8) 0.1758(6) 0.25349(16) 0.0519(7) Uani d . 1 H H5 0.3825 0.1166 0.3003 0.062 Uiso calc R 1 C C13 0.44153(8) 1.0756(6) 0.06709(16) 0.0492(7) Uani d . 1 C C6 0.32113(9) 0.0640(6) 0.23411(16) 0.0506(7) Uani d . 1 H H6 0.3142 -0.0694 0.2678 0.061 Uiso calc R 1 C C12 0.45450(9) 1.2780(7) 0.02073(18) 0.0646(8) Uani d . 1 H H12 0.4829 1.3394 0.0359 0.078 Uiso calc R 1 C C11 0.42538(10) 1.3882(7) -0.04772(18) 0.0621(8) Uani d . 1 H H11 0.4344 1.5219 -0.0788 0.075 Uiso calc R 1 C C14 0.51133(9) 1.0510(9) 0.1620(2) 0.0876(12) Uani d . 1 H H14A 0.5266 0.9471 0.2097 0.131 Uiso calc R 1 H H14B 0.5118 1.2574 0.1731 0.131 Uiso calc R 1 H H14C 0.5247 1.0156 0.1220 0.131 Uiso calc R 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 Br1 0.04646(16) 0.0750(2) 0.0816(2) -0.01226(15) 0.02084(14) 0.0042(2) O2 0.0431(9) 0.0699(12) 0.0585(11) -0.0084(10) -0.0001(8) 0.0139(11) N1 0.0433(11) 0.0431(12) 0.0450(12) -0.0022(9) 0.0125(9) 0.0001(10) C1 0.0409(12) 0.0454(14) 0.0517(15) -0.0011(11) 0.0161(12) -0.0004(13) C8 0.0450(12) 0.0389(12) 0.0427(12) -0.0022(12) 0.0145(10) -0.0045(14) C9 0.0462(14) 0.0480(14) 0.0496(15) -0.0037(11) 0.0098(12) -0.0006(12) O1 0.0456(10) 0.0797(15) 0.0555(11) -0.0110(10) 0.0019(8) 0.0151(11) C3 0.0400(11) 0.0388(14) 0.0403(12) 0.0008(10) 0.0113(10) -0.0036(12) C4 0.0378(13) 0.0453(13) 0.0456(14) 0.0021(10) 0.0083(11) -0.0022(12) C10 0.0612(16) 0.0525(17) 0.0435(15) 0.0005(13) 0.0126(13) 0.0031(13) C2 0.0401(13) 0.0468(14) 0.0452(14) 0.0002(11) 0.0082(11) 0.0006(12) C7 0.0456(14) 0.0432(15) 0.0436(14) 0.0018(11) 0.0093(11) -0.0006(12) C5 0.0508(15) 0.0559(17) 0.0444(15) 0.0025(12) 0.0084(12) 0.0086(14) C13 0.0453(14) 0.0537(17) 0.0458(15) -0.0038(11) 0.0105(12) -0.0015(12) C6 0.0556(15) 0.0505(18) 0.0490(15) -0.0009(12) 0.0211(12) 0.0056(12) C12 0.0513(16) 0.078(2) 0.0624(19) -0.0161(15) 0.0152(14) 0.0107(17) C11 0.0629(18) 0.0669(18) 0.0599(18) -0.0091(15) 0.0241(15) 0.0138(15) C14 0.0432(15) 0.137(4) 0.072(2) -0.0155(19) 0.0029(14) 0.022(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' Br Br -0.2901 2.4595 '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_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle C4 O2 H2 109.5 C7 N1 C8 122.4(2) C2 C1 C6 121.1(2) C2 C1 Br1 119.63(19) C6 C1 Br1 119.26(19) C9 C8 C13 119.1(2) C9 C8 N1 125.0(2) C13 C8 N1 115.8(2) C8 C9 C10 121.0(2) C8 C9 H9 119.5 C10 C9 H9 119.5 C13 O1 C14 117.6(2) C2 C3 C4 119.6(2) C2 C3 C7 119.5(2) C4 C3 C7 120.9(2) O2 C4 C5 118.9(2) O2 C4 C3 122.1(2) C5 C4 C3 119.0(2) C11 C10 C9 119.6(3) C11 C10 H10 120.2 C9 C10 H10 120.2 C1 C2 C3 119.8(2) C1 C2 H22 120.1 C3 C2 H22 120.1 N1 C7 C3 121.0(2) N1 C7 H7 119.5 C3 C7 H7 119.5 C6 C5 C4 120.6(2) C6 C5 H5 119.7 C4 C5 H5 119.7 O1 C13 C12 124.3(2) O1 C13 C8 116.2(2) C12 C13 C8 119.4(3) C5 C6 C1 119.9(2) C5 C6 H6 120.1 C1 C6 H6 120.1 C11 C12 C13 120.2(3) C11 C12 H12 119.9 C13 C12 H12 119.9 C10 C11 C12 120.6(3) C10 C11 H11 119.7 C12 C11 H11 119.7 O1 C14 H14A 109.5 O1 C14 H14B 109.5 H14A C14 H14B 109.5 O1 C14 H14C 109.5 H14A C14 H14C 109.5 H14B C14 H14C 109.5 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag Br1 C1 1.904(2) ? O2 C4 1.338(3) y O2 H2 0.8200 ? N1 C7 1.274(3) y N1 C8 1.413(3) y C1 C2 1.370(4) ? C1 C6 1.376(4) ? C8 C9 1.382(4) ? C8 C13 1.397(3) ? C9 C10 1.383(4) ? C9 H9 0.9300 ? O1 C13 1.358(3) ? O1 C14 1.427(3) ? C3 C2 1.392(3) ? C3 C4 1.404(3) ? C3 C7 1.453(3) y C4 C5 1.392(4) ? C10 C11 1.367(4) ? C10 H10 0.9300 ? C2 H22 0.9300 ? C7 H7 0.9300 ? C5 C6 1.372(4) ? C5 H5 0.9300 ? C13 C12 1.389(4) ? C6 H6 0.9300 ? C12 C11 1.381(4) ? C12 H12 0.9300 ? C11 H11 0.9300 ? C14 H14A 0.9600 ? C14 H14B 0.9600 ? C14 H14C 0.9600 ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA O2 H2 N1 0.82 1.85 2.575(3) 147 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 C7 N1 C8 C9 4.9(4) C7 N1 C8 C13 -175.3(2) C13 C8 C9 C10 0.1(4) N1 C8 C9 C10 179.9(2) C2 C3 C4 O2 -179.6(2) C7 C3 C4 O2 -0.4(4) C2 C3 C4 C5 0.4(4) C7 C3 C4 C5 179.6(2) C8 C9 C10 C11 -0.5(4) C6 C1 C2 C3 -0.2(4) Br1 C1 C2 C3 179.73(19) C4 C3 C2 C1 0.0(4) C7 C3 C2 C1 -179.2(2) C8 N1 C7 C3 179.3(2) C2 C3 C7 N1 179.3(2) C4 C3 C7 N1 0.2(4) O2 C4 C5 C6 179.4(3) C3 C4 C5 C6 -0.6(4) C14 O1 C13 C12 4.7(4) C14 O1 C13 C8 -175.6(3) C9 C8 C13 O1 -179.1(2) N1 C8 C13 O1 1.1(3) C9 C8 C13 C12 0.7(4) N1 C8 C13 C12 -179.1(2) C4 C5 C6 C1 0.4(4) C2 C1 C6 C5 0.0(4) Br1 C1 C6 C5 -179.9(2) O1 C13 C12 C11 178.6(3) C8 C13 C12 C11 -1.1(4) C9 C10 C11 C12 0.1(5) C13 C12 C11 C10 0.7(5) loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 30655360