#------------------------------------------------------------------------------ #$Date: 2025-08-19 11:43:10 +0100 (Tue, 19 Aug 2025) $ #$Revision: 301803 $ #$URL: svn://www.crystallography.net/cod/cif/2/20/22/2202217.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_2202217 loop_ _publ_author_name 'Karaday\?i, Nevzat' 'G\"oz\"uye\;sil, Sanem ' 'G\"uzel, Bilgehan ' 'Kazak ,Canan' 'B\"uy\"ukg\"ung\"or, Orhan' _publ_section_title ; N-[3,5-Bis(trifluoromethyl)phenyl]-3-methoxysalicylaldimine ; _journal_issue 6 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o851 _journal_page_last o853 _journal_paper_doi 10.1107/S1600536803010730 _journal_volume 59 _journal_year 2003 _chemical_formula_iupac 'C16 H11 F6 N O2' _chemical_formula_moiety 'C16 H11 F6 N O2' _chemical_formula_sum 'C16 H11 F6 N O2' _chemical_formula_weight 363.26 _chemical_name_systematic ; N-[3,5-bis(trifluoromethyl)phenyl]-3-methoxysalicylaldimine ; _space_group_IT_number 14 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2yab' _symmetry_space_group_name_H-M 'P 1 21/a 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _cell_angle_alpha 90.00 _cell_angle_beta 116.140(5) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 7.2130(14) _cell_length_b 29.196(4) _cell_length_c 7.8870(16) _cell_measurement_reflns_used 35 _cell_measurement_temperature 180(2) _cell_measurement_theta_max 25 _cell_measurement_theta_min 5 _cell_volume 1491.0(5) _computing_cell_refinement XSCANS _computing_data_collection 'XSCANS (Siemens, 1991)' _computing_data_reduction 'SHELXTL (Bruker,2001)' _computing_molecular_graphics 'ORTEPIII (Burnett & Johnson, 1996)' _computing_publication_material ; WinGX (Farrugia, 1999), PARST (Nardelli, 1995) and PLATON (Spek, 1997) ; _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _diffrn_ambient_temperature 180(2) _diffrn_measured_fraction_theta_full 0.983 _diffrn_measured_fraction_theta_max 0.983 _diffrn_measurement_device_type 'Siemens P4' _diffrn_measurement_method \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 0.0444 _diffrn_reflns_av_sigmaI/netI 0.0320 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_k_max 34 _diffrn_reflns_limit_k_min -34 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_number 17689 _diffrn_reflns_theta_full 25.00 _diffrn_reflns_theta_max 25.00 _diffrn_reflns_theta_min 3.56 _diffrn_standards_decay_% none _diffrn_standards_interval_time 120 _diffrn_standards_number 1 _exptl_absorpt_coefficient_mu 0.157 _exptl_absorpt_correction_type none _exptl_crystal_colour yellow _exptl_crystal_density_diffrn 1.618 _exptl_crystal_density_method 'not measured' _exptl_crystal_description plate _exptl_crystal_F_000 736 _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.01 _refine_diff_density_max 0.403 _refine_diff_density_min -0.296 _refine_ls_extinction_coef 0.0051(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method SHELXL97 _refine_ls_goodness_of_fit_ref 1.125 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 255 _refine_ls_number_reflns 2591 _refine_ls_number_restraints 179 _refine_ls_restrained_S_all 1.109 _refine_ls_R_factor_all 0.0956 _refine_ls_R_factor_gt 0.0695 _refine_ls_shift/su_max 0.060 _refine_ls_shift/su_mean 0.010 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w = 1/[\s^2^(Fo^2^)+(0.0926P)^2^+] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1732 _refine_ls_wR_factor_ref 0.1949 _reflns_number_gt 1891 _reflns_number_total 2591 _reflns_threshold_expression I>2\s(I) _cod_data_source_file wn6153.cif _cod_data_source_block I _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: '_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_values 1715 2011-07-08 13:25:40Z adriana ; _cod_original_sg_symbol_H-M 'P 21/a' _cod_database_code 2202217 _cod_database_fobs_code 2202217 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z' '-x, -y, -z' 'x-1/2, -y-1/2, z' 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 C11 0.5012(5) 0.42955(10) 0.2477(5) 0.0494(8) Uani d D 1 A . C C16 0.6443(6) 0.46950(12) 0.3042(6) 0.0666(10) Uani d DU 1 . . C F4A 0.7690(12) 0.4688(2) 0.2219(11) 0.095(3) Uani d PDU 0.616(17) A 1 F F5A 0.7613(10) 0.4715(2) 0.4821(9) 0.081(2) Uani d PDU 0.616(17) A 1 F F6A 0.5399(10) 0.5091(2) 0.2567(18) 0.116(4) Uani d PDU 0.616(17) A 1 F F4B 0.8416(13) 0.4581(4) 0.360(4) 0.161(9) Uani d PDU 0.384(17) A 2 F F5B 0.652(5) 0.4894(7) 0.459(3) 0.162(8) Uani d PDU 0.384(17) A 2 F F6B 0.608(2) 0.5015(5) 0.1866(16) 0.116(6) Uani d PDU 0.384(17) A 2 F O1 0.4825(3) 0.21511(7) 0.3284(3) 0.0472(6) Uani d . 1 . . O H1 0.4534 0.2414 0.2894 0.071 Uiso calc R 1 . . H O2 0.6126(4) 0.13593(7) 0.4965(3) 0.0589(7) Uani d . 1 . . O N1 0.5042(4) 0.30521(8) 0.3468(3) 0.0404(6) Uani d . 1 . . N C1 0.8777(5) 0.25443(12) 0.7857(5) 0.0530(8) Uani d . 1 . . C H1A 0.9355 0.2814 0.8500 0.064 Uiso calc R 1 . . H C2 0.9467(5) 0.21297(14) 0.8728(5) 0.0591(10) Uani d . 1 . . C H2 1.0523 0.2120 0.9952 0.071 Uiso calc R 1 . . H C3 0.8608(5) 0.17307(13) 0.7802(5) 0.0541(9) Uani d . 1 . . C H3 0.9076 0.1452 0.8409 0.065 Uiso calc R 1 . . H C4 0.7063(5) 0.17384(10) 0.5987(5) 0.0459(8) Uani d . 1 . . C C5 0.6345(4) 0.21577(10) 0.5071(4) 0.0400(7) Uani d . 1 . . C C6 0.7209(4) 0.25630(10) 0.6010(4) 0.0425(7) Uani d . 1 . . C C7 0.6489(5) 0.30035(10) 0.5142(4) 0.0435(7) Uani d . 1 . . C H7 0.7106 0.3265 0.5832 0.052 Uiso calc R 1 . . H C8 0.7141(7) 0.09310(12) 0.5656(6) 0.0729(11) Uani d . 1 . . C H8A 0.6346 0.0689 0.4833 0.109 Uiso calc R 1 . . H H8B 0.7268 0.0878 0.6904 0.109 Uiso calc R 1 . . H H8C 0.8489 0.0939 0.5695 0.109 Uiso calc R 1 . . H C9 0.4415(4) 0.34986(9) 0.2761(4) 0.0394(7) Uani d . 1 A . C C10 0.5772(5) 0.38647(11) 0.3171(5) 0.0481(8) Uani d . 1 . . C H10 0.7180 0.3821 0.3905 0.058 Uiso calc R 1 A . H C12 0.2946(5) 0.43644(10) 0.1331(4) 0.0489(8) Uani d . 1 . . C H12 0.2452 0.4655 0.0873 0.059 Uiso calc R 1 A . H C13 0.1622(4) 0.39965(10) 0.0874(4) 0.0430(7) Uani d . 1 A . C C14 0.2343(4) 0.35660(10) 0.1592(4) 0.0420(7) Uani d . 1 . . C H14 0.1429 0.3321 0.1286 0.050 Uiso calc R 1 A . H C15 -0.0591(5) 0.40608(12) -0.0418(5) 0.0598(9) Uani d . 1 . . C F1 -0.1019(4) 0.39142(11) -0.2155(4) 0.1065(10) Uani d . 1 A . F F2 -0.1826(3) 0.38267(10) 0.0063(4) 0.1091(11) Uani d . 1 A . F F3 -0.1187(4) 0.44886(8) -0.0660(4) 0.1055(10) Uani d . 1 A . F 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 C11 0.0527(18) 0.0379(18) 0.0528(19) -0.0082(14) 0.0188(16) -0.0001(14) C16 0.063(2) 0.050(2) 0.074(3) -0.0132(17) 0.019(2) 0.0028(18) F4A 0.094(5) 0.099(5) 0.102(5) -0.045(4) 0.052(4) -0.003(3) F5A 0.082(4) 0.068(4) 0.066(3) -0.033(3) 0.008(2) -0.009(2) F6A 0.072(3) 0.036(2) 0.192(9) -0.012(2) 0.013(4) 0.008(4) F4B 0.072(5) 0.094(7) 0.26(2) -0.035(4) 0.018(8) 0.019(9) F5B 0.27(2) 0.108(12) 0.130(10) -0.120(13) 0.112(13) -0.066(9) F6B 0.103(9) 0.099(9) 0.095(6) -0.062(7) -0.002(5) 0.049(6) O1 0.0510(12) 0.0376(11) 0.0488(13) 0.0070(9) 0.0181(10) 0.0019(9) O2 0.0706(15) 0.0412(13) 0.0665(15) 0.0131(11) 0.0319(13) 0.0097(11) N1 0.0417(13) 0.0362(14) 0.0456(15) 0.0002(10) 0.0215(12) 0.0002(11) C1 0.0461(17) 0.063(2) 0.0486(19) -0.0059(15) 0.0195(15) 0.0014(16) C2 0.0422(17) 0.083(3) 0.0482(19) 0.0028(17) 0.0159(15) 0.0180(19) C3 0.0471(17) 0.064(2) 0.057(2) 0.0133(16) 0.0284(16) 0.0226(17) C4 0.0469(17) 0.0444(18) 0.055(2) 0.0078(14) 0.0305(16) 0.0074(15) C5 0.0330(14) 0.0467(17) 0.0421(16) 0.0060(12) 0.0181(13) 0.0071(13) C6 0.0384(15) 0.0510(18) 0.0420(16) 0.0018(13) 0.0212(13) 0.0031(14) C7 0.0446(16) 0.0401(17) 0.0500(18) -0.0041(13) 0.0248(15) -0.0033(14) C8 0.091(3) 0.049(2) 0.090(3) 0.026(2) 0.050(2) 0.022(2) C9 0.0448(16) 0.0334(15) 0.0426(16) 0.0013(12) 0.0217(13) -0.0012(12) C10 0.0435(16) 0.0466(18) 0.0525(19) -0.0054(13) 0.0194(14) 0.0017(14) C12 0.0571(19) 0.0339(16) 0.0516(19) -0.0006(13) 0.0203(16) 0.0008(14) C13 0.0451(16) 0.0384(16) 0.0427(17) 0.0005(13) 0.0167(13) -0.0023(13) C14 0.0443(16) 0.0366(16) 0.0433(17) -0.0054(12) 0.0177(13) -0.0054(13) C15 0.0520(19) 0.046(2) 0.065(2) -0.0001(16) 0.0111(17) -0.0034(16) F1 0.0835(17) 0.132(2) 0.0635(16) 0.0026(15) -0.0051(13) -0.0167(15) F2 0.0465(12) 0.119(2) 0.139(2) -0.0020(13) 0.0198(14) 0.0519(18) F3 0.0679(14) 0.0559(15) 0.148(3) 0.0164(11) 0.0063(15) -0.0013(15) 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' F F 0.0171 0.0103 '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 C12 C11 C10 121.2(3) ? C12 C11 C16 119.3(3) yes C10 C11 C16 119.5(3) yes F6B C16 F5A 126.5(7) ? F6B C16 F4A 67.3(8) ? F5A C16 F4A 106.0(5) ? F6B C16 F5B 105.3(10) ? F5A C16 F5B 39.9(12) ? F4A C16 F5B 133.9(9) ? F6B C16 F4B 105.8(9) ? F5A C16 F4B 63.7(10) ? F4A C16 F4B 45.6(10) ? F5B C16 F4B 101.3(11) ? F6B C16 F6A 41.0(7) ? F5A C16 F6A 106.5(6) ? F4A C16 F6A 107.2(6) ? F5B C16 F6A 70.9(11) ? F4B C16 F6A 133.9(6) ? F6B C16 C11 117.9(6) ? F5A C16 C11 113.6(4) ? F4A C16 C11 111.9(4) ? F5B C16 C11 111.2(7) ? F4B C16 C11 113.7(5) ? F6A C16 C11 111.2(4) ? C5 O1 H1 109.5 ? C4 O2 C8 116.6(3) yes C7 N1 C9 118.9(3) yes C2 C1 C6 120.3(3) ? C2 C1 H1A 119.8 ? C6 C1 H1A 119.8 ? C1 C2 C3 120.3(3) ? C1 C2 H2 119.9 ? C3 C2 H2 119.9 ? C4 C3 C2 120.7(3) ? C4 C3 H3 119.6 ? C2 C3 H3 119.6 ? O2 C4 C3 124.6(3) ? O2 C4 C5 115.5(3) yes C3 C4 C5 119.9(3) ? O1 C5 C6 122.4(3) yes O1 C5 C4 118.1(3) yes C6 C5 C4 119.5(3) ? C5 C6 C1 119.3(3) ? C5 C6 C7 121.6(3) yes C1 C6 C7 119.1(3) yes N1 C7 C6 123.2(3) yes N1 C7 H7 118.4 ? C6 C7 H7 118.4 ? O2 C8 H8A 109.5 ? O2 C8 H8B 109.5 ? H8A C8 H8B 109.5 ? O2 C8 H8C 109.5 ? H8A C8 H8C 109.5 ? H8B C8 H8C 109.5 ? C14 C9 C10 119.4(3) ? C14 C9 N1 117.3(3) yes C10 C9 N1 123.3(3) yes C9 C10 C11 119.5(3) ? C9 C10 H10 120.3 ? C11 C10 H10 120.3 ? C13 C12 C11 119.0(3) ? C13 C12 H12 120.5 ? C11 C12 H12 120.5 ? C12 C13 C14 120.7(3) ? C12 C13 C15 119.7(3) yes C14 C13 C15 119.6(3) yes C9 C14 C13 120.3(3) ? C9 C14 H14 119.9 ? C13 C14 H14 119.9 ? F2 C15 F3 108.7(3) ? F2 C15 F1 104.6(3) ? F3 C15 F1 104.1(3) ? F2 C15 C13 113.6(3) ? F3 C15 C13 114.1(3) ? F1 C15 C13 110.9(3) ? 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 C11 C12 . 1.375(5) ? C11 C10 . 1.385(4) ? C11 C16 . 1.489(5) ? C16 F6B . 1.260(8) ? C16 F5A . 1.281(7) ? C16 F4A . 1.322(6) ? C16 F5B . 1.328(10) ? C16 F4B . 1.333(9) ? C16 F6A . 1.340(6) ? O1 C5 . 1.352(3) yes O1 H1 . 0.8200 ? O2 C4 . 1.361(4) yes O2 C8 . 1.430(4) yes N1 C7 . 1.280(4) yes N1 C9 . 1.412(4) yes C1 C2 . 1.372(5) ? C1 C6 . 1.398(4) ? C1 H1A . 0.9300 ? C2 C3 . 1.369(5) ? C2 H2 . 0.9300 ? C3 C4 . 1.373(4) ? C3 H3 . 0.9300 ? C4 C5 . 1.400(4) ? C5 C6 . 1.390(4) ? C6 C7 . 1.442(4) yes C7 H7 . 0.9300 ? C8 H8A . 0.9600 ? C8 H8B . 0.9600 ? C8 H8C . 0.9600 ? C9 C14 . 1.382(4) ? C9 C10 . 1.388(4) ? C10 H10 . 0.9300 ? C12 C13 . 1.376(4) ? C12 H12 . 0.9300 ? C13 C14 . 1.382(4) ? C13 C15 . 1.479(4) ? C14 H14 . 0.9300 ? C15 F2 . 1.305(4) ? C15 F3 . 1.307(4) ? C15 F1 . 1.336(4) ? 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 N1 . 0.82 1.91 2.635(3) 146 yes C7 H7 F1 1_656 0.93 2.46 3.387(4) 175 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 C12 C11 C16 F6B -34.5(13) C10 C11 C16 F6B 147.9(12) C12 C11 C16 F5A 130.3(5) C10 C11 C16 F5A -47.2(6) C12 C11 C16 F4A -109.6(6) C10 C11 C16 F4A 72.8(6) C12 C11 C16 F5B 87.1(16) C10 C11 C16 F5B -90.4(16) C12 C11 C16 F4B -159.3(14) C10 C11 C16 F4B 23.2(14) C12 C11 C16 F6A 10.2(9) C10 C11 C16 F6A -167.3(7) C6 C1 C2 C3 -0.8(5) C1 C2 C3 C4 0.7(5) C8 O2 C4 C3 -15.4(4) C8 O2 C4 C5 165.0(3) C2 C3 C4 O2 -180.0(3) C2 C3 C4 C5 -0.4(5) O2 C4 C5 O1 -0.5(4) C3 C4 C5 O1 179.9(3) O2 C4 C5 C6 179.8(2) C3 C4 C5 C6 0.1(4) O1 C5 C6 C1 -180.0(2) C4 C5 C6 C1 -0.2(4) O1 C5 C6 C7 1.7(4) C4 C5 C6 C7 -178.6(3) C2 C1 C6 C5 0.5(4) C2 C1 C6 C7 178.9(3) C9 N1 C7 C6 178.5(3) C5 C6 C7 N1 -0.7(4) C1 C6 C7 N1 -179.0(3) C7 N1 C9 C14 -144.5(3) C7 N1 C9 C10 36.1(4) C14 C9 C10 C11 3.1(5) N1 C9 C10 C11 -177.5(3) C12 C11 C10 C9 -2.4(5) C16 C11 C10 C9 175.1(3) C10 C11 C12 C13 0.0(5) C16 C11 C12 C13 -177.5(3) C11 C12 C13 C14 1.7(5) C11 C12 C13 C15 -177.6(3) C10 C9 C14 C13 -1.5(4) N1 C9 C14 C13 179.1(3) C12 C13 C14 C9 -0.9(5) C15 C13 C14 C9 178.3(3) C12 C13 C15 F2 -141.0(3) C14 C13 C15 F2 39.7(5) C12 C13 C15 F3 -15.6(5) C14 C13 C15 F3 165.1(3) C12 C13 C15 F1 101.5(4) C14 C13 C15 F1 -77.7(4) loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 PubChem 2809045