#------------------------------------------------------------------------------ #$Date: 2025-08-19 12:01:59 +0200 (Tue, 19 Aug 2025) $ #$Revision: 301802 $ #$URL: svn://www.crystallography.net/cod/cif/2/10/02/2100262.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_2100262 loop_ _publ_author_name 'Skakle, Janet M. S.' 'Low, John N.' 'Wardell, James L.' 'Glidewell, Christopher' _publ_section_title ; Concomitant polymorphism and a temperature-dependent phase change in (E)-[1-(4-methoxyphenyl)-3-phenyl-2-propenylideneamino]oxyacetic acid ; _journal_issue 3 _journal_name_full 'Acta Crystallographica Section B' _journal_page_first 321 _journal_page_last 328 _journal_paper_doi 10.1107/S0108768105007421 _journal_volume 61 _journal_year 2005 _chemical_formula_moiety 'C18 H17 N O4' _chemical_formula_sum 'C18 H17 N O4' _chemical_formula_weight 311.33 _chemical_name_systematic ; (E)-[1-(4-methoxyphenyl)-3-phenyl-2-propenylideneamino)oxyacetic acid ; _space_group_IT_number 14 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_space_group_name_H-M 'P 1 21/c 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _cell_angle_alpha 90.00 _cell_angle_beta 92.947(2) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 6.4499(2) _cell_length_b 14.9693(5) _cell_length_c 16.6559(6) _cell_measurement_reflns_used 3690 _cell_measurement_temperature 120(2) _cell_measurement_theta_max 27.52 _cell_measurement_theta_min 2.98 _cell_volume 1606.01(9) _computing_cell_refinement 'DENZO-SMN (Otwinowski & Minor, 1997)' _computing_data_collection 'Kappa-CCD server software (Nonius, 1997)' _computing_data_reduction DENZO-SMN _computing_molecular_graphics 'PLATON (Spek, 2003)' _computing_publication_material 'SHELXL-97 and PRPKAPPA (Ferguson, 1999)' _computing_structure_refinement 'OSCAIL and SHELXS-97 (Sheldrick, 1997)' _computing_structure_solution 'OSCAIL (McArdle , 2003) and SHELXS-97 (Sheldrick, 1997)' _diffrn_ambient_temperature 120(2) _diffrn_measured_fraction_theta_full 0.997 _diffrn_measured_fraction_theta_max 0.997 _diffrn_measurement_device_type Kappa-CCD _diffrn_measurement_method '\f scans, and \w scans with \k offsets' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed X-ray tube' _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0619 _diffrn_reflns_av_sigmaI/netI 0.0440 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_number 17758 _diffrn_reflns_theta_full 27.52 _diffrn_reflns_theta_max 27.52 _diffrn_reflns_theta_min 2.98 _diffrn_standards_decay_% negligible _exptl_absorpt_coefficient_mu 0.091 _exptl_absorpt_correction_T_max 0.995 _exptl_absorpt_correction_T_min 0.967 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SORTAV (Blessing 1995 and 1997' _exptl_crystal_colour yellow _exptl_crystal_density_diffrn 1.288 _exptl_crystal_density_method 'not measured' _exptl_crystal_description plate _exptl_crystal_F_000 656 _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.05 _refine_diff_density_max 0.656 _refine_diff_density_min -0.639 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.136 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 210 _refine_ls_number_reflns 3690 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.136 _refine_ls_R_factor_all 0.0968 _refine_ls_R_factor_gt 0.0578 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.1318P)^2^+0.4171P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1835 _refine_ls_wR_factor_ref 0.2318 _reflns_number_gt 2647 _reflns_number_total 3690 _reflns_threshold_expression I>2\s(I) _cod_data_source_file ws5022.cif _cod_data_source_block IIa _cod_depositor_comments ; The following automatic conversions were performed: '_exptl_absorpt_correction_type' value 'Multi-scan' changed to 'multi-scan' according to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29. Automatic conversion script Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana ; _cod_original_sg_symbol_H-M 'P 21/c' _cod_database_code 2100262 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x, -y+1/2, z+1/2' '-x, -y, -z' '-x, y-1/2, -z-1/2' loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_type_symbol C1 0.5113(3) 0.56573(15) 0.40172(15) 0.0304(5) Uani d . 1 . . C O2 0.3533(2) 0.52726(11) 0.41955(11) 0.0350(4) Uani d . 1 . . O O1 0.6769(2) 0.57544(12) 0.45065(11) 0.0352(4) Uani d . 1 . . O C11 0.0796(4) 0.43697(15) 0.16447(15) 0.0311(5) Uani d . 1 . . C C12 -0.1059(4) 0.39619(16) 0.18352(17) 0.0367(6) Uani d . 1 . . C C13 -0.1517(4) 0.30945(16) 0.15832(19) 0.0433(7) Uani d . 1 . . C C14 -0.0143(5) 0.26405(18) 0.11227(17) 0.0482(8) Uani d . 1 . . C C15 0.1672(5) 0.30496(18) 0.09115(17) 0.0467(7) Uani d . 1 . . C C16 0.2164(4) 0.39095(17) 0.11727(17) 0.0401(6) Uani d . 1 . . C C2 0.5414(4) 0.60708(16) 0.32101(16) 0.0336(6) Uani d . 1 . . C O3 0.3571(2) 0.61316(10) 0.27205(11) 0.0336(4) Uani d . 1 . . O N4 0.3144(3) 0.52776(12) 0.23787(13) 0.0310(5) Uani d . 1 . . N C5 0.1352(4) 0.52637(15) 0.19887(15) 0.0296(5) Uani d . 1 . . C C6 -0.0067(4) 0.60192(15) 0.19205(15) 0.0299(5) Uani d . 1 . . C C7 -0.1762(4) 0.60633(15) 0.14176(15) 0.0302(5) Uani d . 1 . . C C21 -0.3231(3) 0.68066(15) 0.13578(14) 0.0287(5) Uani d . 1 . . C C26 -0.4999(4) 0.67479(15) 0.08457(15) 0.0321(6) Uani d . 1 . . C C25 -0.6458(4) 0.74346(16) 0.07875(15) 0.0338(6) Uani d . 1 . . C C24 -0.6148(4) 0.81959(15) 0.12510(15) 0.0301(5) Uani d . 1 . . C O24 -0.7452(3) 0.89141(11) 0.12568(11) 0.0390(5) Uani d . 1 . . O C27 -0.9303(4) 0.88886(19) 0.07543(18) 0.0414(7) Uani d . 1 . . C C23 -0.4387(4) 0.82659(15) 0.17666(16) 0.0334(6) Uani d . 1 . . C C22 -0.2960(4) 0.75869(15) 0.18168(15) 0.0308(5) Uani d . 1 . . C H1 0.6613 0.5462 0.4930 0.053 Uiso calc R 1 . . H H12 -0.2021 0.4280 0.2141 0.044 Uiso calc R 1 . . H H13 -0.2768 0.2816 0.1727 0.052 Uiso calc R 1 . . H H14 -0.0445 0.2047 0.0951 0.058 Uiso calc R 1 . . H H15 0.2595 0.2739 0.0584 0.056 Uiso calc R 1 . . H H16 0.3424 0.4182 0.1030 0.048 Uiso calc R 1 . . H H2A 0.5998 0.6678 0.3291 0.040 Uiso calc R 1 . . H H2B 0.6438 0.5712 0.2927 0.040 Uiso calc R 1 . . H H6 0.0228 0.6520 0.2258 0.036 Uiso calc R 1 . . H H7 -0.2029 0.5568 0.1071 0.036 Uiso calc R 1 . . H H26 -0.5218 0.6226 0.0528 0.039 Uiso calc R 1 . . H H25 -0.7653 0.7381 0.0433 0.041 Uiso calc R 1 . . H H27A -0.8948 0.8910 0.0190 0.062 Uiso calc R 1 . . H H27B -1.0175 0.9403 0.0873 0.062 Uiso calc R 1 . . H H27C -1.0061 0.8336 0.0854 0.062 Uiso calc R 1 . . H H23 -0.4172 0.8787 0.2085 0.040 Uiso calc R 1 . . H H22 -0.1763 0.7646 0.2170 0.037 Uiso calc R 1 . . H 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 C1 0.0269(12) 0.0258(11) 0.0385(13) -0.0020(9) 0.0018(10) -0.0055(10) O2 0.0291(9) 0.0370(9) 0.0390(10) -0.0087(7) 0.0025(7) 0.0009(7) O1 0.0320(9) 0.0357(9) 0.0376(10) -0.0111(7) -0.0011(8) 0.0036(7) C11 0.0369(13) 0.0226(11) 0.0333(13) 0.0046(9) -0.0044(10) 0.0009(9) C12 0.0401(14) 0.0270(12) 0.0426(15) 0.0026(10) -0.0030(11) -0.0020(10) C13 0.0466(15) 0.0257(12) 0.0562(17) -0.0023(10) -0.0123(13) 0.0013(11) C14 0.069(2) 0.0279(13) 0.0452(17) 0.0049(12) -0.0194(15) -0.0036(11) C15 0.0655(19) 0.0372(14) 0.0370(15) 0.0181(13) -0.0011(14) -0.0049(12) C16 0.0479(15) 0.0331(13) 0.0391(15) 0.0077(11) 0.0017(12) 0.0027(11) C2 0.0274(12) 0.0300(12) 0.0432(15) -0.0047(9) -0.0004(11) 0.0041(10) O3 0.0323(9) 0.0234(8) 0.0444(10) -0.0015(6) -0.0036(8) 0.0013(7) N4 0.0330(11) 0.0235(9) 0.0365(11) -0.0014(8) 0.0027(9) 0.0019(8) C5 0.0300(12) 0.0258(11) 0.0331(12) -0.0001(9) 0.0038(10) 0.0030(9) C6 0.0313(12) 0.0235(11) 0.0351(13) -0.0002(9) 0.0038(10) 0.0014(9) C7 0.0331(12) 0.0239(11) 0.0336(13) -0.0014(9) 0.0026(10) 0.0007(9) C21 0.0302(12) 0.0242(11) 0.0317(12) 0.0008(9) 0.0009(10) 0.0032(9) C26 0.0372(13) 0.0267(11) 0.0321(13) -0.0016(9) -0.0009(10) -0.0019(10) C25 0.0299(12) 0.0336(12) 0.0372(14) 0.0001(10) -0.0048(10) 0.0023(10) C24 0.0283(12) 0.0260(11) 0.0360(13) 0.0011(9) 0.0022(10) 0.0051(10) O24 0.0338(9) 0.0365(10) 0.0458(11) 0.0103(7) -0.0056(8) -0.0009(8) C27 0.0268(12) 0.0449(15) 0.0523(17) 0.0075(10) -0.0009(11) 0.0024(12) C23 0.0369(13) 0.0247(11) 0.0381(14) -0.0015(9) -0.0033(11) 0.0000(10) C22 0.0297(12) 0.0262(11) 0.0360(13) -0.0005(9) -0.0043(10) 0.0035(10) 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_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_publ_flag O2 C1 O1 124.2(2) no O2 C1 C2 124.1(2) no O1 C1 C2 111.76(19) no C1 O1 H1 109.5 no C16 C11 C12 119.2(2) no C16 C11 C5 120.9(2) no C12 C11 C5 119.8(2) no C13 C12 C11 120.7(3) no C13 C12 H12 119.6 no C11 C12 H12 119.6 no C14 C13 C12 119.7(3) no C14 C13 H13 120.2 no C12 C13 H13 120.2 no C13 C14 C15 120.0(3) no C13 C14 H14 120.0 no C15 C14 H14 120.0 no C14 C15 C16 120.9(3) no C14 C15 H15 119.6 no C16 C15 H15 119.6 no C15 C16 C11 119.6(3) no C15 C16 H16 120.2 no C11 C16 H16 120.2 no O3 C2 C1 113.64(19) no O3 C2 H2A 108.8 no C1 C2 H2A 108.8 no O3 C2 H2B 108.8 no C1 C2 H2B 108.8 no H2A C2 H2B 107.7 no C2 O3 N4 108.30(16) no C5 N4 O3 111.37(17) no N4 C5 C6 124.6(2) no N4 C5 C11 113.41(19) no C6 C5 C11 121.9(2) no C7 C6 C5 125.1(2) no C7 C6 H6 117.5 no C5 C6 H6 117.5 no C6 C7 C21 125.7(2) no C6 C7 H7 117.2 no C21 C7 H7 117.2 no C26 C21 C22 117.5(2) no C26 C21 C7 120.1(2) no C22 C21 C7 122.4(2) no C21 C26 C25 121.7(2) no C21 C26 H26 119.2 no C25 C26 H26 119.2 no C24 C25 C26 119.4(2) no C24 C25 H25 120.3 no C26 C25 H25 120.3 no O24 C24 C25 125.5(2) no O24 C24 C23 114.8(2) no C25 C24 C23 119.7(2) no C24 O24 C27 118.25(19) no O24 C27 H27A 109.5 no O24 C27 H27B 109.5 no H27A C27 H27B 109.5 no O24 C27 H27C 109.5 no H27A C27 H27C 109.5 no H27B C27 H27C 109.5 no C22 C23 C24 120.4(2) no C22 C23 H23 119.8 no C24 C23 H23 119.8 no C23 C22 C21 121.3(2) no C23 C22 H22 119.3 no C21 C22 H22 119.3 no 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 C1 O2 . 1.221(3) no C1 O1 . 1.318(3) no C1 C2 . 1.501(4) no O1 H1 . 0.84 no C11 C16 . 1.394(4) no C11 C12 . 1.394(3) no C11 C5 . 1.492(3) no C12 C13 . 1.392(3) no C12 H12 . 0.95 no C13 C14 . 1.380(4) no C13 H13 . 0.95 no C14 C15 . 1.383(4) no C14 H14 . 0.95 no C15 C16 . 1.390(4) no C15 H15 . 0.95 no C16 H16 . 0.95 no C2 O3 . 1.409(3) no C2 H2A . 0.99 no C2 H2B . 0.99 no O3 N4 . 1.421(2) no N4 C5 . 1.297(3) no C5 C6 . 1.456(3) no C6 C7 . 1.344(3) no C6 H6 . 0.95 no C7 C21 . 1.461(3) no C7 H7 . 0.95 no C21 C26 . 1.391(3) no C21 C22 . 1.402(3) no C26 C25 . 1.393(3) no C26 H26 . 0.95 no C25 C24 . 1.385(3) no C25 H25 . 0.95 no C24 O24 . 1.365(3) no C24 C23 . 1.393(3) no O24 C27 . 1.423(3) no C27 H27A . 0.98 no C27 H27B . 0.98 no C27 H27C . 0.98 no C23 C22 . 1.371(3) no C23 H23 . 0.95 no C22 H22 . 0.95 no 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 _geom_hbond_publ_flag O1 H1 O2 3_666 0.84 1.83 2.668(2) 174 y C23 H23 N4 4_566 0.95 2.48 3.409(3) 166 y C22 H22 Cg1 4_566 0.95 2.85 3.647(3) 142 y 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 _geom_torsion_publ_flag C16 C11 C12 C13 2.2(4) no C5 C11 C12 C13 -173.9(2) no C11 C12 C13 C14 -1.6(4) no C12 C13 C14 C15 -0.3(4) no C13 C14 C15 C16 1.5(4) no C14 C15 C16 C11 -0.9(4) no C12 C11 C16 C15 -1.0(4) no C5 C11 C16 C15 175.1(2) no O2 C1 C2 O3 11.7(3) no O1 C1 C2 O3 -168.81(19) no C1 C2 O3 N4 -78.8(2) no C2 O3 N4 C5 173.23(19) no O3 N4 C5 C6 -1.1(3) no O3 N4 C5 C11 -177.76(18) no C16 C11 C5 N4 -51.8(3) no C12 C11 C5 N4 124.3(2) no C16 C11 C5 C6 131.5(3) no C12 C11 C5 C6 -52.4(3) no N4 C5 C6 C7 168.7(2) no C11 C5 C6 C7 -14.9(4) no C5 C6 C7 C21 178.3(2) no C6 C7 C21 C26 -176.1(2) no C6 C7 C21 C22 2.4(4) no C22 C21 C26 C25 -0.1(3) no C7 C21 C26 C25 178.5(2) no C21 C26 C25 C24 -0.1(4) no C26 C25 C24 O24 -179.6(2) no C26 C25 C24 C23 0.1(4) no C25 C24 O24 C27 0.6(4) no C23 C24 O24 C27 -179.1(2) no O24 C24 C23 C22 179.8(2) no C25 C24 C23 C22 0.1(4) no C24 C23 C22 C21 -0.3(4) no C26 C21 C22 C23 0.3(4) no C7 C21 C22 C23 -178.2(2) no loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 30654442 2 PubChem 12486437