#------------------------------------------------------------------------------ #$Date: 2025-08-19 11:43:10 +0100 (Tue, 19 Aug 2025) $ #$Revision: 301803 $ #$URL: svn://www.crystallography.net/cod/cif/2/20/49/2204988.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_2204988 loop_ _publ_author_name 'Qian, Hui-Fen' 'Huang, Wei' 'Yao, Cheng' _publ_section_title ; 2-Cyano-3-(4-hydroxyphenyl)propenoic acid ; _journal_issue 2 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o370 _journal_page_last o372 _journal_paper_doi 10.1107/S1600536805001224 _journal_volume 61 _journal_year 2005 _chemical_formula_iupac 'C10 H7 N O3' _chemical_formula_moiety 'C10 H7 N O3' _chemical_formula_sum 'C10 H7 N O3' _chemical_formula_weight 189.17 _chemical_melting_point 251.0(10) _chemical_name_common '\a-Cyano-4-hydroxy-cinnamic acid' _chemical_name_systematic ; 2-Cyano-3-(4-hydroxyphenyl)propenoic 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 92.76(2) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 5.839(2) _cell_length_b 9.498(3) _cell_length_c 15.663(5) _cell_measurement_reflns_used 2966 _cell_measurement_temperature 296(2) _cell_measurement_theta_max 27.4835 _cell_measurement_theta_min 3.3728 _cell_volume 867.6(5) _computing_cell_refinement CrystalClear _computing_data_collection 'CrystalClear (Molecular Structure Corporation & Rigaku, 2001)' _computing_data_reduction 'TEXSAN (Molecular Structure Corporation & Rigaku, 2000)' _computing_molecular_graphics SHELXTL _computing_publication_material SHELXTL _computing_structure_refinement SHELXTL _computing_structure_solution 'SHELXTL (Bruker, 2000)' _diffrn_ambient_temperature 296(2) _diffrn_detector_area_resol_mean 14.6199 _diffrn_measured_fraction_theta_full 0.990 _diffrn_measured_fraction_theta_max 0.990 _diffrn_measurement_device_type 'Rigaku Mercury CCD area-detector' _diffrn_measurement_method '\f and \w' _diffrn_radiation_monochromator 'graphite monochromator' _diffrn_radiation_source 'Rigaku rotating anode' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0671 _diffrn_reflns_av_sigmaI/netI 0.0377 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_number 7176 _diffrn_reflns_theta_full 25.00 _diffrn_reflns_theta_max 25.00 _diffrn_reflns_theta_min 3.37 _diffrn_standards_decay_% 0 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.109 _exptl_absorpt_correction_T_max 0.9765 _exptl_absorpt_correction_T_min 0.9690 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(REQAB; Jacobson, 1998)' _exptl_crystal_colour Yellow _exptl_crystal_density_diffrn 1.448 _exptl_crystal_density_meas ? _exptl_crystal_density_method . _exptl_crystal_description Block _exptl_crystal_F_000 392 _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.20 _refine_diff_density_max 0.179 _refine_diff_density_min -0.182 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 0.987 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 129 _refine_ls_number_reflns 1513 _refine_ls_number_restraints 6 _refine_ls_restrained_S_all 0.987 _refine_ls_R_factor_all 0.0646 _refine_ls_R_factor_gt 0.0579 _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^)+(0.0104P)^2^+1.0945P] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1109 _refine_ls_wR_factor_ref 0.1145 _reflns_number_gt 1415 _reflns_number_total 1513 _reflns_threshold_expression I>2\s(I) _cod_data_source_file ac6150.cif _cod_data_source_block I _cod_depositor_comments ; The following automatic conversions were performed: '_chemical_melting_point' value '250-252' was changed to '251.0(10)' - the average value was taken and precision was estimated. Automatic conversion script Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana The following automatic conversions were performed: '_chemical_melting_point' value '250-252' was changed to '251.0(10)' - the average value was taken and precision was estimated. 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 2204988 _cod_database_fobs_code 2204988 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_type_symbol C1 0.2142(4) 0.6175(2) 0.44789(15) 0.0364(5) Uani d . 1 C C2 0.3832(4) 0.7070(2) 0.40645(14) 0.0344(5) Uani d U 1 C C3 0.3631(4) 0.8481(2) 0.40723(15) 0.0367(5) Uani d . 1 C H3A 0.2347 0.8798 0.4344 0.044 Uiso calc R 1 H C4 0.5625(4) 0.6303(2) 0.36806(15) 0.0364(5) Uani d U 1 C C5 0.5000(4) 0.9596(2) 0.37457(15) 0.0348(5) Uani d . 1 C C6 0.4268(4) 1.0979(2) 0.38688(15) 0.0380(6) Uani d . 1 C H6 0.2908 1.1131 0.4141 0.046 Uiso calc R 1 H C7 0.5482(4) 1.2115(2) 0.36033(15) 0.0395(6) Uani d . 1 C H7 0.4949 1.3024 0.3691 0.047 Uiso calc R 1 H C8 0.7513(4) 1.1898(2) 0.32027(15) 0.0373(6) Uani d . 1 C C9 0.8270(4) 1.0539(2) 0.30573(16) 0.0408(6) Uani d . 1 C H9 0.9622 1.0396 0.2779 0.049 Uiso calc R 1 H C10 0.7043(4) 0.9406(2) 0.33206(16) 0.0405(6) Uani d . 1 C H10 0.7566 0.8500 0.3217 0.049 Uiso calc R 1 H N1 0.7021(4) 0.5629(2) 0.33906(14) 0.0483(6) Uani d . 1 N O1 0.2385(3) 0.48550(17) 0.44052(12) 0.0497(5) Uani d . 1 O H1B 0.1334 0.4451 0.4633 0.074 Uiso calc R 1 H O2 0.0579(3) 0.67546(17) 0.48836(12) 0.0493(5) Uani d . 1 O O3 0.8849(3) 1.29617(17) 0.29371(13) 0.0525(5) Uani d . 1 O H3 0.8304 1.3718 0.3079 0.079 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 0.0385(13) 0.0311(12) 0.0397(13) -0.0053(10) 0.0027(10) 0.0002(10) C2 0.0340(12) 0.0321(11) 0.0375(12) -0.0055(9) 0.0069(10) -0.0001(10) C3 0.0358(13) 0.0332(12) 0.0414(13) -0.0041(10) 0.0070(10) -0.0003(10) C4 0.0396(13) 0.0306(11) 0.0394(13) -0.0114(10) 0.0044(11) 0.0049(10) C5 0.0355(12) 0.0287(11) 0.0404(13) -0.0040(9) 0.0043(10) 0.0013(9) C6 0.0353(13) 0.0365(13) 0.0430(14) 0.0001(10) 0.0090(11) -0.0028(10) C7 0.0431(14) 0.0281(11) 0.0480(14) 0.0001(10) 0.0102(11) -0.0033(10) C8 0.0426(13) 0.0298(12) 0.0399(13) -0.0086(10) 0.0059(11) 0.0017(10) C9 0.0374(13) 0.0333(12) 0.0533(15) -0.0019(10) 0.0173(11) -0.0002(11) C10 0.0394(13) 0.0290(11) 0.0541(15) 0.0010(10) 0.0115(11) -0.0008(11) N1 0.0506(13) 0.0347(11) 0.0610(14) -0.0025(10) 0.0175(11) 0.0006(10) O1 0.0472(11) 0.0325(9) 0.0710(13) -0.0102(8) 0.0207(9) 0.0045(9) O2 0.0461(11) 0.0397(10) 0.0639(12) -0.0089(8) 0.0227(9) -0.0048(8) O3 0.0597(12) 0.0303(9) 0.0698(13) -0.0099(8) 0.0262(10) -0.0009(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 124.3(2) y O2 C1 C2 119.0(2) y O1 C1 C2 116.7(2) y C3 C2 C4 125.2(2) y C3 C2 C1 120.6(2) y C4 C2 C1 114.17(19) y C2 C3 C5 132.9(2) y C2 C3 H3A 113.5 ? C5 C3 H3A 113.5 ? N1 C4 C2 176.6(2) y C6 C5 C10 117.2(2) ? C6 C5 C3 117.7(2) ? C10 C5 C3 125.1(2) ? C7 C6 C5 122.2(2) ? C7 C6 H6 118.9 ? C5 C6 H6 118.9 ? C6 C7 C8 119.3(2) ? C6 C7 H7 120.4 ? C8 C7 H7 120.4 ? O3 C8 C7 123.2(2) y O3 C8 C9 116.8(2) y C7 C8 C9 120.0(2) ? C10 C9 C8 120.5(2) ? C10 C9 H9 119.8 ? C8 C9 H9 119.8 ? C9 C10 C5 120.8(2) ? C9 C10 H10 119.6 ? C5 C10 H10 119.6 ? C1 O1 H1B 109.5 ? C8 O3 H3 109.5 ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag C1 O2 1.262(3) y C1 O1 1.267(3) y C1 C2 1.477(3) y C2 C3 1.346(3) y C2 C4 1.431(3) y C3 C5 1.435(3) y C3 H3A 0.9300 ? C4 N1 1.147(3) y C5 C6 1.398(3) ? C5 C10 1.406(3) ? C6 C7 1.367(3) ? C6 H6 0.9300 ? C7 C8 1.383(3) ? C7 H7 0.9300 ? C8 O3 1.354(3) y C8 C9 1.387(3) ? C9 C10 1.367(3) ? C9 H9 0.9300 ? C10 H10 0.9300 ? O1 H1B 0.8200 ? O3 H3 0.8200 ? 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 H1B O2 3_566 0.82 1.79 2.600(2) 168 O3 H3 N1 1_565 0.82 2.03 2.853(3) 178 loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 4485953 2 PubChem 5328791