#------------------------------------------------------------------------------ #$Date: 2025-08-19 12:52:15 +0100 (Tue, 19 Aug 2025) $ #$Revision: 301804 $ #$URL: svn://www.crystallography.net/cod/cif/2/21/44/2214490.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_2214490 loop_ _publ_author_name 'Butcher, Ray J.' 'Jasinski, Jerry P.' 'Narayana, B.' 'Mayekar, Anil N.' 'Yathirajan, H. S.' _publ_section_title ; (2E)-3-(Biphenyl-4-yl)-1-(quinolin-2-yl)prop-2-en-1-one ; _journal_coeditor_code AT2342 _journal_issue 8 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o3546 _journal_page_last o3546 _journal_paper_doi 10.1107/S1600536807034721 _journal_volume 63 _journal_year 2007 _chemical_formula_iupac 'C24 H17 N O' _chemical_formula_moiety 'C24 H17 N O' _chemical_formula_sum 'C24 H17 N O' _chemical_formula_weight 335.39 _chemical_name_systematic ; (2E)-3-(Biphenyl-4-yl)-1-(quinolin-2-yl)prop-2-en-1-one ; _space_group_IT_number 2 _symmetry_cell_setting triclinic _symmetry_space_group_name_Hall '-P 1' _symmetry_space_group_name_H-M 'P -1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _cell_angle_alpha 109.401(12) _cell_angle_beta 92.981(13) _cell_angle_gamma 102.967(15) _cell_formula_units_Z 2 _cell_length_a 5.9808(12) _cell_length_b 11.9617(18) _cell_length_c 13.2239(16) _cell_measurement_reflns_used 5911 _cell_measurement_temperature 203 _cell_measurement_theta_max 32.4156 _cell_measurement_theta_min 4.6315 _cell_volume 861.3(3) _computing_cell_refinement CrysAlisPro _computing_data_collection 'CrysAlisPro (Oxford Diffraction, 2007)' _computing_data_reduction CrysAlisPro _computing_molecular_graphics 'ORTEP-3 (Farrugia, 1997)' _computing_publication_material 'WinGX (Farrugia, 1999)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _diffrn_ambient_temperature 203 _diffrn_detector_area_resol_mean 10.5081 _diffrn_measured_fraction_theta_full 0.991 _diffrn_measured_fraction_theta_max 0.909 _diffrn_measurement_device_type 'Oxford Diffraction Gemini R' _diffrn_measurement_method '\f and \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 0.0226 _diffrn_reflns_av_sigmaI/netI 0.0471 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_number 12993 _diffrn_reflns_theta_full 25.00 _diffrn_reflns_theta_max 32.49 _diffrn_reflns_theta_min 4.63 _diffrn_standards_decay_% 0 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.079 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.92165 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(DENZO/SCALEPACK; Otwinowski & Minor, 1997)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.293 _exptl_crystal_density_method 'not measured' _exptl_crystal_description plate _exptl_crystal_F_000 352 _exptl_crystal_size_max 0.57 _exptl_crystal_size_mid 0.43 _exptl_crystal_size_min 0.19 _refine_diff_density_max 0.276 _refine_diff_density_min -0.297 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.042 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 235 _refine_ls_number_reflns 5643 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.042 _refine_ls_R_factor_all 0.0732 _refine_ls_R_factor_gt 0.0473 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0888P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1292 _refine_ls_wR_factor_ref 0.1484 _reflns_number_gt 3561 _reflns_number_total 5643 _reflns_threshold_expression I>2sigma(I) _cod_data_source_file at2342.cif _cod_data_source_block I _cod_database_code 2214490 _cod_database_fobs_code 2214490 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' 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 O O -0.19597(14) 0.61552(7) 0.49028(7) 0.0421(2) Uani d . 1 N N 0.24910(15) 0.59911(7) 0.32703(7) 0.0276(2) Uani d . 1 C C1 0.14418(18) 0.64559(9) 0.41063(8) 0.0258(2) Uani d . 1 C C2 0.2344(2) 0.76334(9) 0.49132(9) 0.0325(2) Uani d . 1 H H2A 0.1537 0.7920 0.5497 0.039 Uiso calc R 1 C C3 0.4399(2) 0.83407(10) 0.48259(9) 0.0353(3) Uani d . 1 H H3A 0.5034 0.9119 0.5357 0.042 Uiso calc R 1 C C4 0.55752(19) 0.79045(9) 0.39372(9) 0.0315(2) Uani d . 1 C C5 0.7716(2) 0.85790(11) 0.37748(11) 0.0417(3) Uani d . 1 H H5A 0.8394 0.9377 0.4265 0.050 Uiso calc R 1 C C6 0.8798(2) 0.80849(12) 0.29189(11) 0.0440(3) Uani d . 1 H H6A 1.0218 0.8543 0.2825 0.053 Uiso calc R 1 C C7 0.7806(2) 0.68917(11) 0.21717(10) 0.0399(3) Uani d . 1 H H7A 0.8573 0.6558 0.1586 0.048 Uiso calc R 1 C C8 0.5735(2) 0.62167(11) 0.22940(9) 0.0345(3) Uani d . 1 H H8A 0.5086 0.5424 0.1789 0.041 Uiso calc R 1 C C9 0.45601(18) 0.67022(9) 0.31745(8) 0.0279(2) Uani d . 1 C C10 -0.08621(19) 0.56987(9) 0.41909(8) 0.0279(2) Uani d . 1 C C11 -0.17124(19) 0.44328(9) 0.34193(8) 0.0283(2) Uani d . 1 H H11A -0.0762 0.4093 0.2923 0.034 Uiso calc R 1 C C12 -0.38345(18) 0.37616(9) 0.34197(8) 0.0272(2) Uani d . 1 H H12A -0.4748 0.4151 0.3908 0.033 Uiso calc R 1 C C13 -0.48699(17) 0.24784(9) 0.27318(8) 0.0245(2) Uani d . 1 C C14 -0.36185(18) 0.17609(9) 0.20453(9) 0.0305(2) Uani d . 1 H H14A -0.2070 0.2110 0.2001 0.037 Uiso calc R 1 C C15 -0.46337(18) 0.05480(9) 0.14335(9) 0.0307(2) Uani d . 1 H H15A -0.3751 0.0082 0.0987 0.037 Uiso calc R 1 C C16 -0.69470(17) -0.00094(8) 0.14600(8) 0.0248(2) Uani d . 1 C C17 -0.82021(18) 0.07111(9) 0.21369(8) 0.0276(2) Uani d . 1 H H17A -0.9764 0.0368 0.2165 0.033 Uiso calc R 1 C C18 -0.71725(18) 0.19243(9) 0.27675(8) 0.0288(2) Uani d . 1 H H18A -0.8041 0.2385 0.3229 0.035 Uiso calc R 1 C C19 -0.79925(18) -0.13074(9) 0.07668(8) 0.0258(2) Uani d . 1 C C20 -0.6782(2) -0.22039(9) 0.06761(9) 0.0330(2) Uani d . 1 H H20A -0.5313 -0.1987 0.1082 0.040 Uiso calc R 1 C C21 -0.7720(2) -0.34030(10) -0.00032(10) 0.0381(3) Uani d . 1 H H21A -0.6892 -0.3995 -0.0047 0.046 Uiso calc R 1 C C22 -0.9867(2) -0.37409(10) -0.06192(9) 0.0368(3) Uani d . 1 H H22A -1.0477 -0.4553 -0.1095 0.044 Uiso calc R 1 C C23 -1.1119(2) -0.28698(10) -0.05302(9) 0.0344(2) Uani d . 1 H H23A -1.2593 -0.3095 -0.0933 0.041 Uiso calc R 1 C C24 -1.01799(19) -0.16680(9) 0.01560(9) 0.0304(2) Uani d . 1 H H24A -1.1032 -0.1083 0.0212 0.036 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 O 0.0385(5) 0.0370(4) 0.0374(5) 0.0026(4) 0.0143(4) -0.0006(4) N 0.0268(5) 0.0251(4) 0.0284(4) 0.0029(4) 0.0031(3) 0.0090(3) C1 0.0279(5) 0.0221(5) 0.0249(5) 0.0036(4) 0.0000(4) 0.0077(4) C2 0.0395(6) 0.0263(5) 0.0265(5) 0.0051(5) 0.0028(4) 0.0050(4) C3 0.0388(6) 0.0238(5) 0.0345(6) -0.0006(5) -0.0040(5) 0.0059(4) C4 0.0299(6) 0.0278(5) 0.0349(6) 0.0022(4) -0.0028(4) 0.0132(4) C5 0.0358(7) 0.0335(6) 0.0503(7) -0.0036(5) -0.0038(5) 0.0172(5) C6 0.0304(6) 0.0491(7) 0.0580(8) 0.0000(5) 0.0037(6) 0.0328(6) C7 0.0344(6) 0.0506(7) 0.0440(7) 0.0121(5) 0.0113(5) 0.0269(6) C8 0.0342(6) 0.0367(6) 0.0339(6) 0.0085(5) 0.0056(5) 0.0143(5) C9 0.0265(5) 0.0272(5) 0.0302(5) 0.0030(4) 0.0008(4) 0.0134(4) C10 0.0294(5) 0.0258(5) 0.0259(5) 0.0042(4) 0.0039(4) 0.0074(4) C11 0.0309(6) 0.0249(5) 0.0259(5) 0.0049(4) 0.0064(4) 0.0060(4) C12 0.0286(5) 0.0256(5) 0.0246(5) 0.0056(4) 0.0050(4) 0.0061(4) C13 0.0238(5) 0.0241(4) 0.0251(5) 0.0057(4) 0.0039(4) 0.0081(4) C14 0.0223(5) 0.0297(5) 0.0345(6) 0.0037(4) 0.0070(4) 0.0062(4) C15 0.0253(5) 0.0281(5) 0.0349(5) 0.0080(4) 0.0102(4) 0.0048(4) C16 0.0247(5) 0.0221(4) 0.0266(5) 0.0047(4) 0.0048(4) 0.0082(4) C17 0.0222(5) 0.0262(5) 0.0311(5) 0.0040(4) 0.0069(4) 0.0069(4) C18 0.0261(5) 0.0278(5) 0.0300(5) 0.0085(4) 0.0085(4) 0.0051(4) C19 0.0251(5) 0.0240(5) 0.0270(5) 0.0046(4) 0.0063(4) 0.0079(4) C20 0.0295(6) 0.0280(5) 0.0402(6) 0.0076(4) 0.0029(5) 0.0104(5) C21 0.0422(7) 0.0265(5) 0.0442(7) 0.0107(5) 0.0092(5) 0.0088(5) C22 0.0457(7) 0.0244(5) 0.0325(6) 0.0013(5) 0.0065(5) 0.0049(4) C23 0.0317(6) 0.0328(5) 0.0321(6) -0.0004(5) 0.0012(4) 0.0093(4) C24 0.0293(6) 0.0285(5) 0.0328(5) 0.0073(4) 0.0052(4) 0.0100(4) 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 C1 N C9 117.67(9) N C1 C2 123.87(10) N C1 C10 117.76(9) C2 C1 C10 118.36(9) C3 C2 C1 118.77(10) C3 C2 H2A 120.6 C1 C2 H2A 120.6 C2 C3 C4 119.95(10) C2 C3 H3A 120.0 C4 C3 H3A 120.0 C3 C4 C5 123.93(10) C3 C4 C9 117.45(10) C5 C4 C9 118.61(11) C6 C5 C4 120.86(11) C6 C5 H5A 119.6 C4 C5 H5A 119.6 C5 C6 C7 120.50(11) C5 C6 H6A 119.8 C7 C6 H6A 119.8 C8 C7 C6 120.43(11) C8 C7 H7A 119.8 C6 C7 H7A 119.8 C7 C8 C9 120.60(11) C7 C8 H8A 119.7 C9 C8 H8A 119.7 N C9 C8 118.72(10) N C9 C4 122.27(10) C8 C9 C4 119.01(10) O C10 C11 122.40(10) O C10 C1 118.77(9) C11 C10 C1 118.83(9) C12 C11 C10 120.39(9) C12 C11 H11A 119.8 C10 C11 H11A 119.8 C11 C12 C13 126.36(9) C11 C12 H12A 116.8 C13 C12 H12A 116.8 C18 C13 C14 117.74(9) C18 C13 C12 119.83(9) C14 C13 C12 122.41(9) C15 C14 C13 120.71(10) C15 C14 H14A 119.6 C13 C14 H14A 119.6 C14 C15 C16 121.78(9) C14 C15 H15A 119.1 C16 C15 H15A 119.1 C17 C16 C15 117.47(9) C17 C16 C19 122.43(9) C15 C16 C19 120.08(9) C18 C17 C16 120.84(9) C18 C17 H17A 119.6 C16 C17 H17A 119.6 C17 C18 C13 121.44(9) C17 C18 H18A 119.3 C13 C18 H18A 119.3 C24 C19 C20 117.87(9) C24 C19 C16 121.22(9) C20 C19 C16 120.88(9) C21 C20 C19 120.80(10) C21 C20 H20A 119.6 C19 C20 H20A 119.6 C20 C21 C22 120.66(10) C20 C21 H21A 119.7 C22 C21 H21A 119.7 C21 C22 C23 119.56(10) C21 C22 H22A 120.2 C23 C22 H22A 120.2 C24 C23 C22 119.70(11) C24 C23 H23A 120.2 C22 C23 H23A 120.2 C23 C24 C19 121.39(10) C23 C24 H24A 119.3 C19 C24 H24A 119.3 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance O C10 1.2243(13) N C1 1.3211(13) N C9 1.3735(13) C1 C2 1.4192(14) C1 C10 1.5016(15) C2 C3 1.3612(16) C2 H2A 0.9400 C3 C4 1.4113(17) C3 H3A 0.9400 C4 C5 1.4200(16) C4 C9 1.4265(15) C5 C6 1.3613(19) C5 H5A 0.9400 C6 C7 1.4098(18) C6 H6A 0.9400 C7 C8 1.3676(16) C7 H7A 0.9400 C8 C9 1.4165(15) C8 H8A 0.9400 C10 C11 1.4719(14) C11 C12 1.3410(14) C11 H11A 0.9400 C12 C13 1.4677(14) C12 H12A 0.9400 C13 C18 1.3985(14) C13 C14 1.4008(14) C14 C15 1.3791(15) C14 H14A 0.9400 C15 C16 1.4024(14) C15 H15A 0.9400 C16 C17 1.3983(14) C16 C19 1.4836(14) C17 C18 1.3865(14) C17 H17A 0.9400 C18 H18A 0.9400 C19 C24 1.3983(15) C19 C20 1.4003(14) C20 C21 1.3819(15) C20 H20A 0.9400 C21 C22 1.3842(17) C21 H21A 0.9400 C22 C23 1.3918(17) C22 H22A 0.9400 C23 C24 1.3869(15) C23 H23A 0.9400 C24 H24A 0.9400 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 C18 H18A O 2_466 0.94 2.51 3.3222(13) 145.1 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 C9 N C1 C2 -0.94(15) C9 N C1 C10 177.83(8) N C1 C2 C3 0.65(16) C10 C1 C2 C3 -178.11(9) C1 C2 C3 C4 0.80(16) C2 C3 C4 C5 179.59(10) C2 C3 C4 C9 -1.80(15) C3 C4 C5 C6 177.65(11) C9 C4 C5 C6 -0.95(16) C4 C5 C6 C7 0.30(18) C5 C6 C7 C8 0.33(17) C6 C7 C8 C9 -0.28(16) C1 N C9 C8 179.06(9) C1 N C9 C4 -0.18(14) C7 C8 C9 N -179.65(9) C7 C8 C9 C4 -0.38(15) C3 C4 C9 N 1.53(15) C5 C4 C9 N -179.78(9) C3 C4 C9 C8 -177.71(9) C5 C4 C9 C8 0.98(15) N C1 C10 O -173.47(9) C2 C1 C10 O 5.37(15) N C1 C10 C11 6.87(14) C2 C1 C10 C11 -174.29(9) O C10 C11 C12 5.32(16) C1 C10 C11 C12 -175.04(9) C10 C11 C12 C13 -177.31(9) C11 C12 C13 C18 -175.30(10) C11 C12 C13 C14 6.16(16) C18 C13 C14 C15 -0.39(15) C12 C13 C14 C15 178.18(10) C13 C14 C15 C16 0.90(16) C14 C15 C16 C17 -0.21(15) C14 C15 C16 C19 178.34(9) C15 C16 C17 C18 -0.98(14) C19 C16 C17 C18 -179.49(9) C16 C17 C18 C13 1.51(16) C14 C13 C18 C17 -0.80(15) C12 C13 C18 C17 -179.40(9) C17 C16 C19 C24 44.88(14) C15 C16 C19 C24 -133.59(10) C17 C16 C19 C20 -137.29(11) C15 C16 C19 C20 44.24(14) C24 C19 C20 C21 0.50(15) C16 C19 C20 C21 -177.40(10) C19 C20 C21 C22 0.79(17) C20 C21 C22 C23 -1.76(18) C21 C22 C23 C24 1.41(17) C22 C23 C24 C19 -0.11(16) C20 C19 C24 C23 -0.84(15) C16 C19 C24 C23 177.06(9) loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 30655281 2 PubChem 139072604