#------------------------------------------------------------------------------ #$Date: 2025-08-19 12:01:59 +0200 (Tue, 19 Aug 2025) $ #$Revision: 301802 $ #$URL: svn://www.crystallography.net/cod/cif/2/10/02/2100263.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_2100263 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 93.167(2) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 6.4238(3) _cell_length_b 15.1513(9) _cell_length_c 17.0552(9) _cell_measurement_reflns_used 3837 _cell_measurement_temperature 291(2) _cell_measurement_theta_max 27.55 _cell_measurement_theta_min 1.80 _cell_volume 1657.43(15) _computing_cell_refinement 'SAINT (Bruker, 2000)' _computing_data_collection 'SMART (Bruker, 1998)' _computing_data_reduction 'SAINT (Bruker, 2000)' _computing_molecular_graphics ' PLATON (Spek, 2003)' _computing_publication_material 'SHELXL-97 and PRPKAPPA (Ferguson, 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _diffrn_ambient_temperature 291(2) _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measurement_device_type 'Bruker SMART 1000 CCD area detector' _diffrn_measurement_method \f-\w _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 0.0382 _diffrn_reflns_av_sigmaI/netI 0.0326 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_number 13953 _diffrn_reflns_theta_full 27.55 _diffrn_reflns_theta_max 27.55 _diffrn_reflns_theta_min 1.80 _diffrn_standards_decay_% negligible _exptl_absorpt_coefficient_mu 0.089 _exptl_absorpt_correction_T_max 0.996 _exptl_absorpt_correction_T_min 0.982 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SADABS; Bruker, 2000)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.248 _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 0.152 _refine_diff_density_min -0.137 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 0.984 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 210 _refine_ls_number_reflns 3837 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 0.984 _refine_ls_R_factor_all 0.0931 _refine_ls_R_factor_gt 0.0490 _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^)+(0.0795P)^2^+0.0527P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1360 _refine_ls_wR_factor_ref 0.1513 _reflns_number_gt 2171 _reflns_number_total 3837 _reflns_threshold_expression I>2\s(I) _cod_data_source_file ws5022.cif _cod_data_source_block IIb _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 2100263 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 O1 0.6749(2) 0.57149(10) 0.44883(8) 0.0731(4) Uani d . 1 . . O O2 0.35075(19) 0.52460(10) 0.42022(8) 0.0715(4) Uani d . 1 . . O O3 0.35183(19) 0.60586(8) 0.27465(8) 0.0655(4) Uani d . 1 . . O O24 -0.7423(2) 0.88371(10) 0.12369(9) 0.0827(5) Uani d . 1 . . O N4 0.3106(2) 0.52168(9) 0.24115(9) 0.0589(4) Uani d . 1 . . N C1 0.5087(3) 0.56167(12) 0.40199(11) 0.0576(5) Uani d . 1 . . C C2 0.5374(3) 0.60012(13) 0.32253(12) 0.0638(5) Uani d . 1 . . C C5 0.1331(3) 0.52079(11) 0.20183(10) 0.0549(4) Uani d . 1 . . C C6 -0.0105(3) 0.59500(11) 0.19403(11) 0.0575(4) Uani d . 1 . . C C7 -0.1774(3) 0.59977(12) 0.14494(11) 0.0576(4) Uani d . 1 . . C C11 0.0793(3) 0.43272(12) 0.16713(11) 0.0595(5) Uani d . 1 . . C C12 -0.1032(3) 0.39073(13) 0.18608(13) 0.0733(6) Uani d . 1 . . C C13 -0.1463(4) 0.30646(15) 0.15944(16) 0.0896(7) Uani d . 1 . . C C14 -0.0131(5) 0.26365(17) 0.11396(15) 0.0972(9) Uani d . 1 . . C C15 0.1652(5) 0.30432(17) 0.09294(14) 0.0970(8) Uani d . 1 . . C C16 0.2143(4) 0.38905(14) 0.12045(13) 0.0788(6) Uani d . 1 . . C C21 -0.3237(3) 0.67349(11) 0.13728(10) 0.0536(4) Uani d . 1 . . C C22 -0.2960(3) 0.75123(12) 0.18074(11) 0.0622(5) Uani d . 1 . . C C23 -0.4369(3) 0.81881(12) 0.17438(12) 0.0670(5) Uani d . 1 . . C C24 -0.6123(3) 0.81232(13) 0.12425(11) 0.0614(5) Uani d . 1 . . C C27 -0.9292(3) 0.88148(17) 0.07492(15) 0.0883(7) Uani d . 1 . . C C25 -0.6452(3) 0.73650(14) 0.08002(12) 0.0674(5) Uani d . 1 . . C C26 -0.4998(3) 0.66828(13) 0.08728(11) 0.0651(5) Uani d . 1 . . C H1 0.6609 0.5435 0.4894 0.110 Uiso calc R 1 . . H H2A 0.5964 0.6588 0.3289 0.077 Uiso calc R 1 . . H H2B 0.6368 0.5642 0.2960 0.077 Uiso calc R 1 . . H H12 -0.1969 0.4196 0.2169 0.088 Uiso calc R 1 . . H H13 -0.2684 0.2787 0.1729 0.108 Uiso calc R 1 . . H H14 -0.0430 0.2065 0.0970 0.117 Uiso calc R 1 . . H H15 0.2542 0.2755 0.0602 0.116 Uiso calc R 1 . . H H16 0.3378 0.4159 0.1073 0.095 Uiso calc R 1 . . H H6 0.0175 0.6434 0.2264 0.069 Uiso calc R 1 . . H H7 -0.2040 0.5515 0.1122 0.069 Uiso calc R 1 . . H H22 -0.1788 0.7571 0.2148 0.075 Uiso calc R 1 . . H H23 -0.4143 0.8697 0.2042 0.080 Uiso calc R 1 . . H H27A -0.8953 0.8811 0.0208 0.132 Uiso calc R 1 . . H H27B -1.0118 0.9326 0.0850 0.132 Uiso calc R 1 . . H H27C -1.0066 0.8292 0.0861 0.132 Uiso calc R 1 . . H H25 -0.7626 0.7312 0.0459 0.081 Uiso calc R 1 . . H H26 -0.5223 0.6175 0.0574 0.078 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 O1 0.0626(8) 0.0832(10) 0.0719(9) -0.0270(7) -0.0102(7) 0.0086(7) O2 0.0558(7) 0.0877(10) 0.0707(8) -0.0206(7) 0.0021(6) 0.0051(7) O3 0.0661(8) 0.0492(7) 0.0792(9) -0.0051(6) -0.0124(7) 0.0042(6) O24 0.0735(9) 0.0773(9) 0.0947(11) 0.0247(7) -0.0188(8) -0.0045(8) N4 0.0633(9) 0.0475(9) 0.0652(9) -0.0029(7) -0.0026(8) 0.0031(7) C1 0.0509(10) 0.0543(10) 0.0673(11) -0.0077(8) 0.0001(9) -0.0052(9) C2 0.0553(11) 0.0610(11) 0.0741(12) -0.0123(9) -0.0054(9) 0.0066(9) C5 0.0591(10) 0.0500(10) 0.0554(10) -0.0005(8) 0.0011(8) 0.0051(8) C6 0.0597(11) 0.0465(10) 0.0657(11) -0.0001(8) -0.0015(9) -0.0004(8) C7 0.0629(11) 0.0502(10) 0.0589(10) -0.0008(8) -0.0034(9) 0.0015(8) C11 0.0668(12) 0.0497(10) 0.0606(11) 0.0073(9) -0.0095(9) 0.0021(8) C12 0.0744(13) 0.0556(11) 0.0889(15) -0.0018(10) -0.0042(11) -0.0004(10) C13 0.0964(16) 0.0584(13) 0.1106(18) -0.0066(12) -0.0255(15) -0.0016(13) C14 0.135(2) 0.0598(14) 0.0920(17) 0.0059(15) -0.0358(18) -0.0120(12) C15 0.139(2) 0.0751(16) 0.0759(15) 0.0344(16) -0.0012(16) -0.0107(12) C16 0.0901(15) 0.0689(13) 0.0777(14) 0.0156(11) 0.0079(12) -0.0018(11) C21 0.0541(10) 0.0501(10) 0.0558(10) -0.0033(8) -0.0043(8) 0.0057(8) C22 0.0577(10) 0.0536(10) 0.0727(12) -0.0011(9) -0.0185(9) 0.0021(9) C23 0.0678(12) 0.0513(10) 0.0796(13) 0.0017(9) -0.0170(11) -0.0053(9) C24 0.0566(10) 0.0607(11) 0.0659(11) 0.0043(9) -0.0055(9) 0.0057(9) C27 0.0576(12) 0.0967(17) 0.1090(18) 0.0169(11) -0.0097(12) 0.0088(14) C25 0.0588(11) 0.0716(13) 0.0695(12) -0.0012(10) -0.0165(9) 0.0045(10) C26 0.0712(12) 0.0582(11) 0.0643(11) -0.0027(9) -0.0114(10) -0.0035(9) 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 124.19(17) no O2 C1 C2 123.94(16) no O1 C1 C2 111.86(15) no C1 O1 H1 109.5 no O3 C2 C1 113.97(15) 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 108.14(13) no C5 N4 O3 111.05(14) no N4 C5 C6 125.21(16) no N4 C5 C11 113.21(15) no C6 C5 C11 121.50(16) no C16 C11 C12 118.76(19) no C16 C11 C5 121.23(19) no C12 C11 C5 119.86(18) no C13 C12 C11 120.3(2) no C13 C12 H12 119.8 no C11 C12 H12 119.8 no C14 C13 C12 120.8(2) no C14 C13 H13 119.6 no C12 C13 H13 119.6 no C13 C14 C15 120.0(2) no C13 C14 H14 120.0 no C15 C14 H14 120.0 no C14 C15 C16 120.2(2) no C14 C15 H15 119.9 no C16 C15 H15 119.9 no C11 C16 C15 119.8(2) no C11 C16 H16 120.1 no C15 C16 H16 120.1 no C7 C6 C5 125.89(17) no C7 C6 H6 117.1 no C5 C6 H6 117.1 no C6 C7 C21 126.31(17) no C6 C7 H7 116.8 no C21 C7 H7 116.8 no C26 C21 C22 116.85(16) no C26 C21 C7 120.83(16) no C22 C21 C7 122.31(15) no C23 C22 C21 121.65(16) no C23 C22 H22 119.2 no C21 C22 H22 119.2 no C22 C23 C24 120.68(17) no C22 C23 H23 119.7 no C24 C23 H23 119.7 no O24 C24 C23 115.22(17) no O24 C24 C25 125.32(17) no C23 C24 C25 119.46(17) no C24 O24 C27 118.77(17) 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 C24 C25 C26 119.05(17) no C24 C25 H25 120.5 no C26 C25 H25 120.5 no C21 C26 C25 122.30(18) no C21 C26 H26 118.8 no C25 C26 H26 118.8 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 . 1.215(2) no C1 O1 . 1.306(2) no C1 C2 . 1.496(3) no O1 H1 . 0.82 no C2 O3 . 1.410(2) no C2 H2A . 0.97 no C2 H2B . 0.97 no O3 N4 . 1.4165(18) no N4 C5 . 1.291(2) no C5 C6 . 1.456(2) no C5 C11 . 1.493(2) no C11 C16 . 1.379(3) no C11 C12 . 1.387(3) no C12 C13 . 1.378(3) no C12 H12 . 0.93 no C13 C14 . 1.352(4) no C13 H13 . 0.93 no C14 C15 . 1.366(4) no C14 H14 . 0.93 no C15 C16 . 1.397(3) no C15 H15 . 0.93 no C16 H16 . 0.93 no C6 C7 . 1.326(2) no C6 H6 . 0.93 no C7 C21 . 1.461(2) no C7 H7 . 0.93 no C21 C26 . 1.381(2) no C21 C22 . 1.398(2) no C22 C23 . 1.367(2) no C22 H22 . 0.93 no C23 C24 . 1.380(2) no C23 H23 . 0.93 no C24 O24 . 1.366(2) no C24 C25 . 1.384(3) no O24 C27 . 1.423(2) no C27 H27A . 0.96 no C27 H27B . 0.96 no C27 H27C . 0.96 no C25 C26 . 1.394(3) no C25 H25 . 0.93 no C26 H26 . 0.93 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 0.82 1.86 2.679(2) 175 y C23 H23 N4 2_555 0.93 2.56 3.472(2) 167 y C22 H22 Cg1 2_555 0.93 2.94 3.712(2) 141 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 O2 C1 C2 O3 12.1(3) no O1 C1 C2 O3 -168.96(16) no C1 C2 O3 N4 -80.63(18) no C2 O3 N4 C5 174.60(15) no O3 N4 C5 C6 -1.6(2) no O3 N4 C5 C11 -178.36(14) no N4 C5 C11 C16 -53.7(2) no C6 C5 C11 C16 129.4(2) no N4 C5 C11 C12 121.89(19) no C6 C5 C11 C12 -55.0(2) no C16 C11 C12 C13 0.9(3) no C5 C11 C12 C13 -174.80(19) no C11 C12 C13 C14 -0.6(3) no C12 C13 C14 C15 -0.9(4) no C13 C14 C15 C16 2.2(4) no C12 C11 C16 C15 0.3(3) no C5 C11 C16 C15 176.0(2) no C14 C15 C16 C11 -1.9(3) no N4 C5 C6 C7 169.29(17) no C11 C5 C6 C7 -14.2(3) no C5 C6 C7 C21 179.27(16) no C6 C7 C21 C26 -175.84(18) no C6 C7 C21 C22 2.8(3) no C26 C21 C22 C23 0.3(3) no C7 C21 C22 C23 -178.36(17) no C21 C22 C23 C24 -0.1(3) no C22 C23 C24 O24 179.32(17) no C22 C23 C24 C25 0.0(3) no C23 C24 O24 C27 -178.57(18) no C25 C24 O24 C27 0.8(3) no O24 C24 C25 C26 -179.26(18) no C23 C24 C25 C26 0.0(3) no C22 C21 C26 C25 -0.3(3) no C7 C21 C26 C25 178.38(17) no C24 C25 C26 C21 0.1(3) no loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 30654442 2 PubChem 12486437