#------------------------------------------------------------------------------ #$Date: 2025-08-18 23:52:38 +0100 (Mon, 18 Aug 2025) $ #$Revision: 301791 $ #$URL: svn://www.crystallography.net/cod/cif/2/00/85/2008536.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_2008536 loop_ _publ_author_name 'Borbulevych, Oleg Ya.' 'Golding, Igor R.' 'Kharitonkin, Andrey B.' 'Shishkin, Oleg V.' 'Gololobov, Yuriy G.' _publ_section_title ; The N-phenylamide of 2-cyano-5-phenylpent-2-en-4-ynoic acid ; _journal_issue 6 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 1019 _journal_page_last 1020 _journal_paper_doi 10.1107/S0108270199002218 _journal_volume 55 _journal_year 1999 _chemical_formula_sum 'C18 H12 N2 O' _chemical_formula_weight 272.30 _chemical_name_systematic ; N-phenylamide of 2-cyano-5-phenylpent-2-en-4-ynoic 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' _audit_creation_method SHELXL _cell_angle_alpha 90.00(3) _cell_angle_beta 94.57(4) _cell_angle_gamma 90.00(3) _cell_formula_units_Z 4 _cell_length_a 11.662(5) _cell_length_b 14.323(7) _cell_length_c 8.700(4) _cell_measurement_reflns_used 24 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 11 _cell_measurement_theta_min 10 _cell_volume 1448.6(12) _computing_cell_refinement P3 _computing_data_collection 'P3 (Siemens, 1989)' _computing_data_reduction 'SHELXTL (Sheldrick, 1994)' _computing_molecular_graphics SHELXTL _computing_publication_material SHELXTL _computing_structure_refinement SHELXTL _computing_structure_solution SHELXTL _diffrn_ambient_temperature 293(2) _diffrn_measurement_device 'Siemens P3/PC' _diffrn_measurement_method '\q/2\q scans' _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 0.0300 _diffrn_reflns_av_sigmaI/netI 0.0735 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_k_max 0 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_number 3381 _diffrn_reflns_theta_max 27.06 _diffrn_reflns_theta_min 1.75 _diffrn_standards_decay_% 5 _diffrn_standards_interval_count 98 _diffrn_standards_number 2 _exptl_absorpt_coefficient_mu 0.079 _exptl_absorpt_correction_type none _exptl_crystal_colour yellow _exptl_crystal_density_diffrn 1.249 _exptl_crystal_density_method 'not measured' _exptl_crystal_description Needle _exptl_crystal_F_000 568 _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.20 _refine_diff_density_max 0.215 _refine_diff_density_min -0.146 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_all 0.860 _refine_ls_goodness_of_fit_ref 1.092 _refine_ls_hydrogen_treatment refall _refine_ls_matrix_type full _refine_ls_number_parameters 226 _refine_ls_number_reflns 3113 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.060 _refine_ls_restrained_S_obs 1.092 _refine_ls_R_factor_all 0.1255 _refine_ls_R_factor_gt 0.0487 _refine_ls_shift/esd_mean 0.000 _refine_ls_shift/su_max -0.001 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^)+(0.0762P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_all 0.1521 _refine_ls_wR_factor_ref 0.1131 _reflns_number_gt 1683 _reflns_number_total 3171 _reflns_observed_criterion >2sigma(I) _cod_data_source_file bm1318.cif _cod_data_source_block gam _cod_depositor_comments ; The following automatic conversions were performed: '_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic' 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_enum 1527 2010-12-29 10:47:43Z saulius The following automatic conversions were performed: '_refine_ls_weighting_scheme' value 'calc w = 1/[\s^2^(Fo^2^)+(0.0762P)^2^] where P=(Fo^2^+2Fc^2^)/3' was changed to 'calc'. New tag '_refine_ls_weighting_details' was created. The value of the new tag was set to 'w = 1/[\s^2^(Fo^2^)+(0.0762P)^2^] where P=(Fo^2^+2Fc^2^)/3'. Automatic conversion script Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas ; _cod_original_cell_volume 1448.5(11) _cod_original_sg_symbol_H-M 'P 21/c' _cod_database_code 2008536 _cod_database_fobs_code 2008536 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_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 N1 .0635(11) .0872(13) .0662(12) .0210(10) -.0112(9) -.0024(10) N2 .0401(7) .0470(8) .0453(8) .0058(6) -.0018(6) .0031(7) O1 .0626(8) .0570(8) .0538(8) .0155(6) -.0078(6) -.0065(6) C1 .0397(9) .0417(9) .0450(10) .0012(7) -.0026(8) .0018(8) C2 .0365(8) .0446(9) .0492(10) .0011(7) -.0019(8) .0061(8) C3 .0482(10) .0520(10) .0626(12) .0096(9) -.0028(9) .0021(9) C4 .0469(10) .0538(10) .0684(12) .0074(9) .0022(9) -.0006(10) C5 .0463(10) .0476(10) .0694(12) .0056(8) .0043(9) .0040(9) C6 .0388(9) .0549(10) .0535(12) .0118(8) -.0022(8) .0075(9) C7 .0416(9) .0369(9) .0622(12) .0023(7) -.0001(8) -.0009(8) C8 .0699(14) .0695(14) .0637(14) .0245(11) .0148(11) .0044(11) C9 .092(2) .083(2) .0614(14) .0286(14) -.0030(13) .0068(12) C10 .0546(12) .0528(11) .083(2) .0115(9) -.0094(11) -.0003(11) C11 .0452(10) .0503(11) .0784(14) .0070(9) .0041(10) -.0099(10) C12 .0496(11) .0562(11) .0581(12) .0035(9) -.0008(9) -.0077(9) C13 .0355(8) .0446(9) .0434(9) .0035(7) .0000(7) .0054(7) C14 .0463(10) .0459(10) .0689(13) .0028(8) -.0060(9) -.0001(9) C15 .0476(11) .0675(13) .0669(13) .0106(10) -.0134(10) -.0010(10) C16 .0556(12) .0602(12) .0610(12) .0170(10) .0017(10) .0141(10) C17 .0633(13) .0456(11) .0758(14) .0069(10) .0019(11) .0045(10) C18 .0492(11) .0465(10) .0636(13) .0030(8) -.0032(9) .0010(9) loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_thermal_displace_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_disorder_group _atom_site_type_symbol N1 -.1584(2) .32742(13) -.3510(2) .0732(5) Uani d . 1 . N N2 .04546(12) .25544(10) -.0411(2) .0444(4) Uani d . 1 . N H2 .0274(15) .2436(12) -.145(2) .053 Uiso d . 1 . H O1 .01104(11) .34829(9) .16112(15) .0585(4) Uani d . 1 . O C1 -.00813(14) .32622(11) .0268(2) .0424(4) Uani d . 1 . C C2 -.09999(14) .37584(11) -.0719(2) .0437(4) Uani d . 1 . C C3 -.1576(2) .44481(13) -.0076(2) .0547(5) Uani d . 1 . C H3 -.1380(16) .4600(13) .097(2) .066 Uiso d . 1 . H C4 -.2509(2) .49458(13) -.0818(2) .0565(5) Uani d . 1 . C C5 -.3329(2) .53517(12) -.1375(2) .0545(5) Uani d . 1 . C C6 -.13046(15) .34899(13) -.2270(2) .0494(4) Uani d . 1 . C C7 -.43244(14) .58356(11) -.2058(2) .0471(4) Uani d . 1 . C C8 -.4498(2) .5912(2) -.3627(3) .0672(6) Uani d . 1 . C H8 -.4020(19) .5672(16) -.432(2) .081 Uiso d . 1 . H C9 -.5469(2) .6368(2) -.4291(3) .0793(7) Uani d . 1 . C H9 -.559(2) .6404(16) -.542(3) .095 Uiso d . 1 . H C10 -.6245(2) .67385(14) -.3369(3) .0641(6) Uani d . 1 . C H10 -.6935(19) .7037(16) -.386(2) .077 Uiso d . 1 . H C11 -.6076(2) .66685(13) -.1815(3) .0580(5) Uani d . 1 . C H11 -.6621(18) .6963(14) -.116(2) .070 Uiso d . 1 . H C12 -.5118(2) .62171(13) -.1123(2) .0549(5) Uani d . 1 . C H12 -.5013(18) .6175(14) .004(3) .066 Uiso d . 1 . H C13 .12653(14) .19541(11) .0402(2) .0413(4) Uani d . 1 . C C14 .2102(2) .22997(13) .1456(2) .0542(5) Uani d . 1 . C H14 .2159(16) .2951(15) .162(2) .065 Uiso d . 1 . H C15 .2866(2) .16978(15) .2238(3) .0616(5) Uani d . 1 . C H15 .3453(19) .1942(14) .305(2) .074 Uiso d . 1 . H C16 .2790(2) .07504(14) .1977(2) .0591(5) Uani d . 1 . C H16 .3279(18) .0335(14) .257(2) .071 Uiso d . 1 . H C17 .1969(2) .04138(15) .0913(3) .0618(5) Uani d . 1 . C H17 .1895(17) -.0238(16) .065(2) .074 Uiso d . 1 . H C18 .1199(2) .10077(13) .0115(2) .0535(5) Uani d . 1 . C H18 .0633(17) .0799(13) -.070(2) .064 Uiso d . 1 . H 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 C1 N2 C13 123.19(15) yes O1 C1 N2 124.08(15) yes O1 C1 C2 119.8(2) yes N2 C1 C2 116.05(15) yes C3 C2 C6 120.0(2) yes C3 C2 C1 117.9(2) yes C6 C2 C1 122.0(2) yes C2 C3 C4 125.0(2) yes C5 C4 C3 176.3(2) yes C4 C5 C7 179.5(2) yes N1 C6 C2 177.9(2) yes C8 C7 C12 119.9(2) no C8 C7 C5 120.1(2) no C12 C7 C5 120.0(2) no C7 C8 C9 120.2(2) no C10 C9 C8 119.6(2) no C11 C10 C9 120.5(2) no C10 C11 C12 121.1(2) no C11 C12 C7 118.7(2) no C14 C13 C18 120.0(2) no C14 C13 N2 121.4(2) no C18 C13 N2 118.57(15) no C13 C14 C15 120.0(2) no C16 C15 C14 120.2(2) no C17 C16 C15 119.5(2) no C16 C17 C18 121.0(2) no C13 C18 C17 119.3(2) no loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag N1 C6 . . 1.144(2) yes N2 C1 . . 1.352(2) yes N2 C13 . . 1.424(2) yes O1 C1 . . 1.214(2) yes C1 C2 . . 1.498(2) yes C2 C3 . . 1.342(3) yes C2 C6 . . 1.421(3) yes C3 C4 . . 1.414(3) yes C4 C5 . . 1.189(2) yes C5 C7 . . 1.439(2) yes C7 C8 . . 1.368(3) ? C7 C12 . . 1.392(3) ? C8 C9 . . 1.391(3) ? C9 C10 . . 1.364(3) ? C10 C11 . . 1.354(3) ? C11 C12 . . 1.386(3) ? C13 C14 . . 1.377(2) ? C13 C18 . . 1.379(3) ? C14 C15 . . 1.380(3) ? C15 C16 . . 1.377(3) ? C16 C17 . . 1.365(3) ? C17 C18 . . 1.383(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 _geom_hbond_publ_flag N2 H2 O1 4_565 0.93(2) 2.14(2) 2.985(2) 152(2) yes 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 C13 N2 C1 O1 3.5(3) no C13 N2 C1 C2 -173.68(14) no O1 C1 C2 C3 0.9(2) no N2 C1 C2 C3 178.1(2) no O1 C1 C2 C6 -176.2(2) no N2 C1 C2 C6 1.1(2) no C6 C2 C3 C4 1.1(3) no C1 C2 C3 C4 -176.0(2) no C2 C3 C4 C5 126.(3) no C3 C4 C5 C7 -9.E1(2) no C3 C2 C6 N1 -46.(6) no C1 C2 C6 N1 131.(6) no C4 C5 C7 C8 -6.E1(2) no C4 C5 C7 C12 12.E1(2) no C12 C7 C8 C9 -0.3(3) no C5 C7 C8 C9 179.0(2) no C7 C8 C9 C10 0.1(4) no C8 C9 C10 C11 0.1(4) no C9 C10 C11 C12 -0.3(3) no C10 C11 C12 C7 0.2(3) no C8 C7 C12 C11 0.1(3) no C5 C7 C12 C11 -179.2(2) no C1 N2 C13 C14 40.55(8) yes C1 N2 C13 C18 136.5(2) no C18 C13 C14 C15 -0.6(3) no N2 C13 C14 C15 179.3(2) no C13 C14 C15 C16 -0.6(3) no C14 C15 C16 C17 1.6(3) no C15 C16 C17 C18 -1.3(3) no C14 C13 C18 C17 0.9(3) no N2 C13 C18 C17 -179.0(2) no C16 C17 C18 C13 0.0(3) no loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 21183046 2 PubChem 100985108