#------------------------------------------------------------------------------ #$Date: 2025-08-19 15:49:58 +0100 (Tue, 19 Aug 2025) $ #$Revision: 301806 $ #$URL: svn://www.crystallography.net/cod/cif/2/23/88/2238864.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_2238864 loop_ _publ_author_name 'Usha, M. K.' 'Ramaprasad, G. C.' 'Kalluraya, Balakrishna' 'Kant, Rajni' 'Gupta, Vivek K.' 'Revannasiddaiah, D.' _publ_section_title ; 5-(5'-Fluoro-2'-methoxybiphenyl-3-yl)-1,3,4-oxadiazol-2-amine ; _journal_issue 12 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o1788 _journal_paper_doi 10.1107/S1600536813031206 _journal_volume 69 _journal_year 2013 _chemical_formula_iupac 'C15 H12 F N3 O2' _chemical_formula_moiety 'C15 H12 F N3 O2' _chemical_formula_sum 'C15 H12 F N3 O2' _chemical_formula_weight 285.28 _chemical_name_systematic ; 5-(5'-Fluoro-2'-methoxybiphenyl-3-yl)-1,3,4-oxadiazol-2-amine ; _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 _audit_creation_method SHELXL-97 _cell_angle_alpha 90.00 _cell_angle_beta 90.341(7) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 12.9105(9) _cell_length_b 6.1738(4) _cell_length_c 16.9255(11) _cell_measurement_reflns_used 1316 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 27.96 _cell_measurement_theta_min 4.07 _cell_volume 1349.05(16) _computing_cell_refinement 'CrysAlis PRO (Oxford Diffraction, 2010)' _computing_data_collection 'CrysAlis PRO (Oxford Diffraction, 2010)' _computing_data_reduction 'CrysAlis PRO (Oxford Diffraction, 2010)' _computing_molecular_graphics 'ORTEP-3 for Windows (Farrugia, 2012) and Mercury (Macrae et al., 2008)' _computing_publication_material 'PLATON (Spek, 2009)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)' _computing_structure_solution 'SHELXS97 (Sheldrick, 2008)' _diffrn_ambient_temperature 293(2) _diffrn_detector_area_resol_mean 16.1049 _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.998 _diffrn_measurement_device_type 'Oxford Diffraction Xcalibur Sapphire3 CCD' _diffrn_measurement_method '\w 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 0.0481 _diffrn_reflns_av_sigmaI/netI 0.0907 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_k_max 4 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_number 5027 _diffrn_reflns_theta_full 26.00 _diffrn_reflns_theta_max 26.00 _diffrn_reflns_theta_min 3.51 _diffrn_standards_decay_% 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.105 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.80602 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(CrysAlis RED; Oxford Diffraction, 2010)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.405 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 592 _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _refine_diff_density_max 0.177 _refine_diff_density_min -0.178 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.006 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 191 _refine_ls_number_reflns 2650 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.006 _refine_ls_R_factor_all 0.1157 _refine_ls_R_factor_gt 0.0535 _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^)+(0.0316P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1046 _refine_ls_wR_factor_ref 0.1346 _reflns_number_gt 1382 _reflns_number_total 2650 _reflns_threshold_expression I>2\s(I) _iucr_refine_instructions_details ; TITL BK4 in P2(1)/c CELL 0.71073 12.9105 6.1738 16.9255 90.000 90.341 90.000 ZERR 4.00 0.0009 0.0004 0.0011 0.000 0.007 0.000 LATT 1 SYMM - X, 1/2 + Y, 1/2 - Z SFAC C H N O F UNIT 60 48 12 8 4 MERG 2 OMIT -3.00 52.00 FMAP 2 PLAN 10 ACTA BOND $H CONF L.S. 4 WGHT 0.031600 FVAR 5.18980 O1 4 0.890217 0.044335 0.569435 11.00000 0.05925 0.02892 = 0.03505 0.00157 -0.01662 0.00033 C2 1 0.933650 0.050836 0.643014 11.00000 0.04610 0.03084 = 0.03009 0.00167 -0.01223 0.00267 N3 3 0.954508 -0.140453 0.670770 11.00000 0.06151 0.03270 = 0.03603 0.00109 -0.01556 0.00376 N4 3 0.921734 -0.286473 0.611214 11.00000 0.05529 0.03525 = 0.04121 0.00197 -0.01220 0.00258 C5 1 0.884798 -0.174530 0.553867 11.00000 0.04572 0.02792 = 0.03450 -0.00084 -0.00352 -0.00063 N6 3 0.947389 0.243440 0.675749 11.00000 0.08142 0.03045 = 0.04436 -0.00408 -0.02920 0.00139 AFIX 93 H6A 2 0.973818 0.253425 0.722367 11.00000 -1.20000 H6B 2 0.929888 0.358623 0.650404 11.00000 -1.20000 AFIX 0 C7 1 0.842875 -0.244348 0.478390 11.00000 0.04811 0.03387 = 0.03623 0.00138 -0.00615 -0.00334 C8 1 0.860190 -0.457808 0.453294 11.00000 0.05642 0.03262 = 0.04705 0.00769 -0.00826 -0.00021 AFIX 43 H8 2 0.895904 -0.554890 0.485441 11.00000 -1.20000 AFIX 0 C9 1 0.823547 -0.521316 0.380430 11.00000 0.06105 0.03628 = 0.04655 -0.00397 -0.00496 -0.00037 AFIX 43 H9 2 0.836262 -0.661471 0.362839 11.00000 -1.20000 AFIX 0 C10 1 0.768213 -0.380429 0.332996 11.00000 0.06036 0.04029 = 0.03908 -0.00718 -0.01268 -0.00484 AFIX 43 H10 2 0.743867 -0.426756 0.284011 11.00000 -1.20000 AFIX 0 C11 1 0.748528 -0.169432 0.357875 11.00000 0.04480 0.03837 = 0.03310 -0.00350 -0.01040 -0.00264 C12 1 0.785628 -0.104272 0.431386 11.00000 0.04607 0.03594 = 0.03934 -0.00268 -0.01033 -0.00021 AFIX 43 H12 2 0.771846 0.035169 0.449255 11.00000 -1.20000 AFIX 0 C13 1 0.692882 -0.018170 0.303774 11.00000 0.04404 0.04321 = 0.03594 -0.00602 -0.01224 -0.00170 C14 1 0.720706 -0.012617 0.224253 11.00000 0.04649 0.05832 = 0.04688 0.00078 -0.00329 0.00301 AFIX 43 H14 2 0.773053 -0.102657 0.205886 11.00000 -1.20000 AFIX 0 C15 1 0.670852 0.125720 0.173068 11.00000 0.05332 0.06615 = 0.03763 0.01130 -0.00433 -0.00130 F15 5 0.700170 0.126169 0.095981 11.00000 0.08978 0.12110 = 0.04300 0.02199 0.00499 0.01346 C16 1 0.595111 0.262870 0.196715 11.00000 0.06348 0.05202 = 0.04360 0.01066 -0.01320 -0.00169 AFIX 43 H16 2 0.563725 0.357411 0.161122 11.00000 -1.20000 AFIX 0 C17 1 0.565446 0.258493 0.275917 11.00000 0.05625 0.05501 = 0.04366 0.00014 -0.00967 0.00978 AFIX 43 H17 2 0.512220 0.347978 0.293152 11.00000 -1.20000 AFIX 0 C18 1 0.614658 0.122120 0.328788 11.00000 0.04942 0.04604 = 0.03665 0.00193 -0.01264 -0.00238 O19 4 0.586667 0.104920 0.406435 11.00000 0.07548 0.06538 = 0.04328 -0.00335 -0.00166 0.02189 C20 1 0.520854 0.266830 0.438198 11.00000 0.13056 0.09163 = 0.05866 -0.01229 0.00539 0.04364 AFIX 137 H20A 2 0.550564 0.407081 0.429044 11.00000 -1.50000 H20B 2 0.513375 0.244078 0.493983 11.00000 -1.50000 H20C 2 0.454120 0.258811 0.413047 11.00000 -1.50000 HKLF 4 END ; _cod_data_source_file hb7155.cif _cod_data_source_block I _cod_original_sg_symbol_H-M 'P 21/c' _cod_database_code 2238864 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_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 _atom_site_symmetry_multiplicity O O1 0.89022(14) 0.0443(3) 0.56943(11) 0.0411(5) Uani d . 1 1 C C2 0.9336(2) 0.0508(4) 0.64301(15) 0.0357(7) Uani d . 1 1 N N3 0.95451(18) -0.1405(3) 0.67077(13) 0.0435(6) Uani d . 1 1 N N4 0.92173(18) -0.2865(3) 0.61121(14) 0.0440(6) Uani d . 1 1 C C5 0.8848(2) -0.1745(4) 0.55387(16) 0.0361(7) Uani d . 1 1 N N6 0.94739(18) 0.2434(3) 0.67575(14) 0.0522(7) Uani d . 1 1 H H6A 0.9738 0.2534 0.7224 0.063 Uiso calc R 1 1 H H6B 0.9299 0.3586 0.6504 0.063 Uiso calc R 1 1 C C7 0.8429(2) -0.2443(4) 0.47839(16) 0.0394(7) Uani d . 1 1 C C8 0.8602(2) -0.4578(4) 0.45329(17) 0.0454(8) Uani d . 1 1 H H8 0.8959 -0.5549 0.4854 0.054 Uiso calc R 1 1 C C9 0.8235(2) -0.5213(4) 0.38043(18) 0.0480(8) Uani d . 1 1 H H9 0.8363 -0.6615 0.3628 0.058 Uiso calc R 1 1 C C10 0.7682(2) -0.3804(4) 0.33300(17) 0.0466(8) Uani d . 1 1 H H10 0.7439 -0.4268 0.2840 0.056 Uiso calc R 1 1 C C11 0.7485(2) -0.1694(4) 0.35787(16) 0.0388(7) Uani d . 1 1 C C12 0.7856(2) -0.1043(4) 0.43139(16) 0.0405(7) Uani d . 1 1 H H12 0.7718 0.0352 0.4493 0.049 Uiso calc R 1 1 C C13 0.6929(2) -0.0182(4) 0.30377(17) 0.0411(7) Uani d . 1 1 C C14 0.7207(2) -0.0126(5) 0.22425(18) 0.0506(8) Uani d . 1 1 H H14 0.7731 -0.1027 0.2059 0.061 Uiso calc R 1 1 C C15 0.6709(2) 0.1257(5) 0.17307(18) 0.0524(9) Uani d . 1 1 F F15 0.70017(16) 0.1262(3) 0.09598(11) 0.0846(7) Uani d . 1 1 C C16 0.5951(3) 0.2629(5) 0.19672(19) 0.0531(9) Uani d . 1 1 H H16 0.5637 0.3574 0.1611 0.064 Uiso calc R 1 1 C C17 0.5654(2) 0.2585(5) 0.27592(17) 0.0517(9) Uani d . 1 1 H H17 0.5122 0.3480 0.2932 0.062 Uiso calc R 1 1 C C18 0.6147(2) 0.1221(4) 0.32879(17) 0.0441(8) Uani d . 1 1 O O19 0.58667(17) 0.1049(3) 0.40644(12) 0.0614(7) Uani d . 1 1 C C20 0.5209(3) 0.2668(6) 0.4382(2) 0.0936(14) Uani d . 1 1 H H20A 0.5506 0.4071 0.4290 0.140 Uiso calc R 1 1 H H20B 0.5134 0.2441 0.4940 0.140 Uiso calc R 1 1 H H20C 0.4541 0.2588 0.4130 0.140 Uiso calc R 1 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 O1 0.0593(13) 0.0289(9) 0.0351(11) 0.0003(9) -0.0166(10) 0.0016(9) C2 0.0461(17) 0.0308(14) 0.0301(16) 0.0027(12) -0.0122(14) 0.0017(13) N3 0.0615(17) 0.0327(12) 0.0360(15) 0.0038(11) -0.0156(13) 0.0011(12) N4 0.0553(16) 0.0352(13) 0.0412(15) 0.0026(11) -0.0122(14) 0.0020(11) C5 0.0457(17) 0.0279(14) 0.0345(17) -0.0006(12) -0.0035(14) -0.0008(13) N6 0.0814(19) 0.0304(12) 0.0444(16) 0.0014(12) -0.0292(15) -0.0041(12) C7 0.0481(17) 0.0339(15) 0.0362(18) -0.0033(13) -0.0061(15) 0.0014(14) C8 0.0564(19) 0.0326(14) 0.0471(19) -0.0002(14) -0.0083(16) 0.0077(14) C9 0.061(2) 0.0363(15) 0.047(2) -0.0004(14) -0.0050(17) -0.0040(15) C10 0.060(2) 0.0403(17) 0.0391(18) -0.0048(14) -0.0127(16) -0.0072(14) C11 0.0448(18) 0.0384(15) 0.0331(17) -0.0026(13) -0.0104(15) -0.0035(13) C12 0.0461(17) 0.0359(15) 0.0393(18) -0.0002(13) -0.0103(15) -0.0027(14) C13 0.0440(18) 0.0432(17) 0.0359(18) -0.0017(13) -0.0122(15) -0.0060(14) C14 0.0465(19) 0.058(2) 0.047(2) 0.0030(15) -0.0033(16) 0.0008(17) C15 0.053(2) 0.066(2) 0.0376(19) -0.0013(17) -0.0043(17) 0.0113(17) F15 0.0898(16) 0.1211(17) 0.0430(12) 0.0135(13) 0.0050(12) 0.0220(12) C16 0.063(2) 0.052(2) 0.044(2) -0.0017(17) -0.0132(18) 0.0107(17) C17 0.056(2) 0.0550(19) 0.044(2) 0.0098(16) -0.0097(17) 0.0001(17) C18 0.0494(19) 0.0460(17) 0.0367(18) -0.0024(14) -0.0126(16) 0.0019(15) O19 0.0755(17) 0.0654(15) 0.0433(14) 0.0219(12) -0.0017(13) -0.0034(12) C20 0.131(4) 0.092(3) 0.059(3) 0.044(3) 0.005(3) -0.012(2) 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' F F 0.0171 0.0103 '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 C2 O1 C5 102.9(2) N3 C2 N6 129.7(3) N3 C2 O1 112.8(2) N6 C2 O1 117.5(2) C2 N3 N4 105.1(2) C5 N4 N3 107.7(2) N4 C5 O1 111.5(2) N4 C5 C7 130.0(2) O1 C5 C7 118.6(2) C2 N6 H6A 120.0 C2 N6 H6B 120.0 H6A N6 H6B 120.0 C12 C7 C8 119.9(3) C12 C7 C5 121.0(2) C8 C7 C5 119.1(2) C9 C8 C7 119.0(3) C9 C8 H8 120.5 C7 C8 H8 120.5 C8 C9 C10 121.1(3) C8 C9 H9 119.5 C10 C9 H9 119.5 C9 C10 C11 120.6(3) C9 C10 H10 119.7 C11 C10 H10 119.7 C12 C11 C10 118.6(3) C12 C11 C13 122.1(2) C10 C11 C13 119.3(2) C7 C12 C11 120.9(2) C7 C12 H12 119.6 C11 C12 H12 119.6 C14 C13 C18 117.9(3) C14 C13 C11 118.8(3) C18 C13 C11 123.3(3) C15 C14 C13 120.1(3) C15 C14 H14 120.0 C13 C14 H14 120.0 C16 C15 F15 119.1(3) C16 C15 C14 122.6(3) F15 C15 C14 118.3(3) C15 C16 C17 118.3(3) C15 C16 H16 120.9 C17 C16 H16 120.9 C18 C17 C16 120.4(3) C18 C17 H17 119.8 C16 C17 H17 119.8 O19 C18 C17 123.1(3) O19 C18 C13 116.0(3) C17 C18 C13 120.8(3) C18 O19 C20 118.1(3) O19 C20 H20A 109.5 O19 C20 H20B 109.5 H20A C20 H20B 109.5 O19 C20 H20C 109.5 H20A C20 H20C 109.5 H20B C20 H20C 109.5 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance O1 C2 1.363(3) O1 C5 1.378(3) C2 N3 1.299(3) C2 N6 1.323(3) N3 N4 1.415(3) N4 C5 1.281(3) C5 C7 1.450(3) N6 H6A 0.8600 N6 H6B 0.8600 C7 C12 1.386(3) C7 C8 1.403(3) C8 C9 1.375(4) C8 H8 0.9300 C9 C10 1.380(4) C9 H9 0.9300 C10 C11 1.393(3) C10 H10 0.9300 C11 C12 1.390(3) C11 C13 1.490(4) C12 H12 0.9300 C13 C14 1.396(4) C13 C18 1.398(4) C14 C15 1.374(4) C14 H14 0.9300 C15 C16 1.356(4) C15 F15 1.361(3) C16 C17 1.397(4) C16 H16 0.9300 C17 C18 1.381(4) C17 H17 0.9300 C18 O19 1.369(3) O19 C20 1.420(3) C20 H20A 0.9600 C20 H20B 0.9600 C20 H20C 0.9600 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 N6 H6A N3 2_756 0.86 2.131 2.972(3) 166 y N6 H6B N4 1_565 0.86 2.292 3.118(3) 161 y C17 H17 Cg3 2_655 0.93 2.72 3.53 146 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 C5 O1 C2 N3 0.6(3) C5 O1 C2 N6 -178.7(2) N6 C2 N3 N4 178.8(3) O1 C2 N3 N4 -0.4(3) C2 N3 N4 C5 0.0(3) N3 N4 C5 O1 0.4(3) N3 N4 C5 C7 178.7(3) C2 O1 C5 N4 -0.6(3) C2 O1 C5 C7 -179.2(2) N4 C5 C7 C12 165.3(3) O1 C5 C7 C12 -16.4(4) N4 C5 C7 C8 -14.2(5) O1 C5 C7 C8 164.1(2) C12 C7 C8 C9 2.8(4) C5 C7 C8 C9 -177.7(3) C7 C8 C9 C10 -1.6(4) C8 C9 C10 C11 0.3(4) C9 C10 C11 C12 -0.1(4) C9 C10 C11 C13 177.2(3) C8 C7 C12 C11 -2.7(4) C5 C7 C12 C11 177.8(3) C10 C11 C12 C7 1.3(4) C13 C11 C12 C7 -175.8(3) C12 C11 C13 C14 133.5(3) C10 C11 C13 C14 -43.7(4) C12 C11 C13 C18 -45.5(4) C10 C11 C13 C18 137.3(3) C18 C13 C14 C15 -0.8(4) C11 C13 C14 C15 -179.8(2) C13 C14 C15 C16 1.0(5) C13 C14 C15 F15 -179.9(3) F15 C15 C16 C17 179.4(3) C14 C15 C16 C17 -1.6(5) C15 C16 C17 C18 1.9(5) C16 C17 C18 O19 -177.6(3) C16 C17 C18 C13 -1.8(5) C14 C13 C18 O19 177.3(3) C11 C13 C18 O19 -3.7(4) C14 C13 C18 C17 1.2(4) C11 C13 C18 C17 -179.8(3) C17 C18 O19 C20 -14.6(4) C13 C18 O19 C20 169.5(3) loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 PubChem 139086210