#------------------------------------------------------------------------------ #$Date: 2021-09-06 15:30:52 +0300 (Mon, 06 Sep 2021) $ #$Revision: 268944 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/15/81/7158166.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/ # # All data on this site have been placed in the public domain by the # contributors. # data_7158166 loop_ _publ_author_name 'Kobayashi, Yusuke' 'Masakado, Sota' 'Murai, Takuya' 'Hamada, Shohei' 'Furuta, Takumi' 'Takemoto, Yoshiji' _publ_section_title ; A bench-stable N-trifluoroacetyl nitrene equivalent for a simple synthesis of 2-trifluoromethyl oxazoles. ; _journal_issue 30 _journal_name_full 'Organic & biomolecular chemistry' _journal_page_first 6628 _journal_page_last 6632 _journal_paper_doi 10.1039/d1ob00947h _journal_volume 19 _journal_year 2021 _chemical_formula_moiety 'C8 H4 F3 I N2 O3' _chemical_formula_sum 'C8 H4 F3 I N2 O3' _chemical_formula_weight 360.03 _chemical_melting_point 118.0(10) _chemical_name_systematic SM569 _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_Hall '-P 2ybc' _space_group_name_H-M_alt 'P 1 21/c 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary dual _audit_creation_date 2017-10-12 _audit_creation_method ; Olex2 1.2-ac3 (compiled 2016.03.30 svn.r3266 for Rigaku Oxford Diffraction, GUI svn.r5168) ; _audit_update_record ; 2021-04-27 deposited with the CCDC. 2021-07-07 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 101.298(4) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 4.9637(2) _cell_length_b 20.0442(7) _cell_length_c 10.3335(4) _cell_measurement_reflns_used 4927 _cell_measurement_temperature 93 _cell_measurement_theta_max 72.8460 _cell_measurement_theta_min 4.4010 _cell_volume 1008.19(7) _computing_cell_refinement 'CrysAlisPro 1.171.39.32e (Rigaku OD, 2017)' _computing_data_collection 'CrysAlisPro 1.171.39.32e (Rigaku OD, 2017)' _computing_data_reduction 'CrysAlisPro 1.171.39.32e (Rigaku OD, 2017)' _computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 (Dolomanov et al., 2009)' _computing_structure_refinement 'ShelXL (Sheldrick, 2015)' _computing_structure_solution 'ShelXT (Sheldrick, 2015)' _diffrn_ambient_temperature 93 _diffrn_detector 'CCD plate' _diffrn_measured_fraction_theta_full 0.993 _diffrn_measured_fraction_theta_max 0.969 _diffrn_measurement_details ; List of Runs (angles in degrees, time in seconds): # Type Start End Width t~exp~ \w \q \k \f Frames #-------------------------------------------------------------------------- 1 \w -88.00 90.00 0.50 0.50 -- 0.90 29.00 120.00 356 2 \w -84.00 -38.00 0.50 1.04 -- 5.00 60.00 0.00 92 3 \w -188.00 -35.00 0.50 1.04 -- -98.40 57.00 90.00 306 4 \w -188.00 -35.00 0.50 1.04 -- -98.40 57.00 60.00 306 5 \w -188.00 -9.00 0.50 1.04 -- -98.40 43.00 150.00 358 6 \w -188.00 -35.00 0.50 1.04 -- -98.40 57.00 60.00 306 7 \w -188.00 -38.00 0.50 1.04 -- -98.40 60.00 150.00 300 8 \w -188.00 -38.00 0.50 1.04 -- -98.40 60.00 0.00 300 9 \w -90.00 -38.00 0.50 0.50 -- -0.90 60.00 90.00 104 10 \w -188.00-110.00 0.50 1.04 -- -98.40 0.00 150.00 156 11 \w -188.00 -9.00 0.50 1.04 -- -98.40 0.00 0.00 358 ; _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'XtaLAB AFC11 (RCD3): quarter-chi single' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_type 'CrysAlisPro convention (1999,Acta A55,543-557)' _diffrn_orient_matrix_UB_11 0.0165057000 _diffrn_orient_matrix_UB_12 -0.0653566000 _diffrn_orient_matrix_UB_13 0.0796123000 _diffrn_orient_matrix_UB_21 -0.0346352000 _diffrn_orient_matrix_UB_22 -0.0404306000 _diffrn_orient_matrix_UB_23 -0.1289541000 _diffrn_orient_matrix_UB_31 0.3142264000 _diffrn_orient_matrix_UB_32 -0.0010419000 _diffrn_orient_matrix_UB_33 0.0115457000 _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54184 _diffrn_reflns_av_R_equivalents 0.0469 _diffrn_reflns_av_unetI/netI 0.0259 _diffrn_reflns_Laue_measured_fraction_full 0.993 _diffrn_reflns_Laue_measured_fraction_max 0.969 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_h_min -4 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_number 9201 _diffrn_reflns_point_group_measured_fraction_full 0.993 _diffrn_reflns_point_group_measured_fraction_max 0.969 _diffrn_reflns_theta_full 67.684 _diffrn_reflns_theta_max 73.260 _diffrn_reflns_theta_min 4.412 _diffrn_source 'fine-focus sealed X-ray tube' _diffrn_source_type 'Enhance (Cu) X-ray Source' _exptl_absorpt_coefficient_mu 25.461 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.10978 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro 1.171.39.32e (Rigaku Oxford Diffraction, 2017) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour 'clear light colourless' _exptl_crystal_colour_lustre clear _exptl_crystal_colour_modifier light _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 2.372 _exptl_crystal_description needle _exptl_crystal_F_000 680 _exptl_crystal_preparation condensation _exptl_crystal_recrystallization_method pyridine-ether _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.1 _exptl_crystal_size_min 0.1 _refine_diff_density_max 3.497 _refine_diff_density_min -3.623 _refine_diff_density_rms 0.268 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.118 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 154 _refine_ls_number_reflns 1959 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.118 _refine_ls_R_factor_all 0.0650 _refine_ls_R_factor_gt 0.0641 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.1324P)^2^+3.8932P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1774 _refine_ls_wR_factor_ref 0.1789 _reflns_Friedel_coverage 0.000 _reflns_number_gt 1908 _reflns_number_total 1959 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d1ob00947h2.cif _cod_data_source_block exp_218 _cod_depositor_comments ; The following automatic conversions were performed: data item '_chemical_melting_point' value '117-119' was changed to '118.0(10)' -- the average value was taken and precision was estimated. Automatic conversion script Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas Adding full bibliography for 7158166.cif. ; _cod_database_code 7158166 _chemical_oxdiff_formula 'C20 H16 F12 I4 N20 O12 ' _shelx_space_group_comment ; The symmetry employed for this shelxl refinement is uniquely defined by the following loop, which should always be used as a source of symmetry information in preference to the above space-group names. They are only intended as comments. ; _reflns_odcompleteness_completeness 99.30 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 66.97 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups 2.a Aromatic/amide H refined with riding coordinates: C5(H5), C6(H6), C4(H4), C3(H3) ; _shelx_res_file ; TITL exp_218_a.res in P2(1)/c exp_218.res created by SHELXL-2016/6 at 23:27:26 on 12-Oct-2017 REM Old TITL exp_218 in P2(1)/c REM SHELXT solution in P2(1)/c REM R1 0.087, Rweak 0.007, Alpha 0.033, Orientation as input REM Formula found by SHELXT: C9 N15 O3 F3 I CELL 1.54184 4.9637 20.0442 10.3335 90 101.298 90 ZERR 4 0.0002 0.0007 0.0004 0 0.004 0 LATT 1 SYMM -X,0.5+Y,0.5-Z SFAC C H F I N O UNIT 32 16 12 4 8 12 L.S. 4 PLAN 5 TEMP -180.15 BOND $H LIST 6 MORE -1 CONF fmap 2 ACTA REM REM REM WGHT 0.132400 3.893200 FVAR 2.17937 I7 4 0.537403 0.384278 0.470712 11.00000 0.02622 0.02514 = 0.02926 -0.00199 0.00847 0.00315 F13 3 1.096273 0.447063 0.178926 11.00000 0.04447 0.04097 = 0.04900 0.00637 0.02665 0.00446 F11 3 0.730183 0.502397 0.103468 11.00000 0.05056 0.05030 = 0.03478 0.00999 0.00520 0.00803 F12 3 1.049247 0.546509 0.249211 11.00000 0.07087 0.03843 = 0.05235 -0.00847 0.02617 -0.02143 O17 6 0.241362 0.318619 0.618790 11.00000 0.02833 0.03657 = 0.03013 -0.00339 0.00539 0.00064 O16 6 0.160975 0.216529 0.666789 11.00000 0.02976 0.04707 = 0.03347 -0.00082 0.00939 -0.00423 O14 6 0.670492 0.506226 0.386241 11.00000 0.06821 0.03207 = 0.05318 -0.00406 0.03530 0.00710 N15 5 0.273321 0.257442 0.608162 11.00000 0.02059 0.03787 = 0.02272 0.00270 0.00349 -0.00169 N8 5 0.767997 0.399425 0.331042 11.00000 0.02711 0.02865 = 0.02832 0.00246 0.00696 0.00136 C2 1 0.452195 0.234920 0.522161 11.00000 0.02078 0.03083 = 0.02101 -0.00340 0.00005 -0.00089 C1 1 0.586308 0.280500 0.453625 11.00000 0.02302 0.01587 = 0.02491 -0.00077 0.00165 0.00663 C5 1 0.782760 0.187978 0.357780 11.00000 0.02471 0.03061 = 0.02806 -0.00393 0.00852 -0.00024 AFIX 43 H5 2 0.897184 0.171440 0.301334 11.00000 -1.20000 AFIX 0 C6 1 0.751452 0.256404 0.369378 11.00000 0.02145 0.02654 = 0.02271 -0.00107 0.00448 -0.00211 AFIX 43 H6 2 0.841316 0.286386 0.320583 11.00000 -1.20000 AFIX 0 C4 1 0.651787 0.143488 0.426209 11.00000 0.02196 0.02758 = 0.02562 -0.00349 0.00913 -0.00197 AFIX 43 H4 2 0.675438 0.096875 0.416080 11.00000 -1.20000 AFIX 0 C3 1 0.486665 0.166465 0.509256 11.00000 0.02735 0.02517 = 0.03592 0.00094 0.00952 0.00257 AFIX 43 H3 2 0.397269 0.135958 0.557207 11.00000 -1.20000 AFIX 0 C10 1 0.919594 0.489294 0.214951 11.00000 0.03849 0.02683 = 0.03465 -0.00273 0.00555 -0.00343 C9 1 0.775065 0.464605 0.322619 11.00000 0.03064 0.02985 = 0.03178 -0.00615 0.00147 0.00465 HKLF 4 REM exp_218_a.res in P2(1)/c REM R1 = 0.0641 for 1908 Fo > 4sig(Fo) and 0.0650 for all 1959 data REM 154 parameters refined using 0 restraints END WGHT 0.1326 3.9041 REM Highest difference peak 3.497, deepest hole -3.623, 1-sigma level 0.268 Q1 1 0.4434 0.3672 0.5284 11.00000 0.05 3.50 Q2 1 0.6564 0.4145 0.3938 11.00000 0.05 1.83 Q3 1 0.6477 0.3575 0.4134 11.00000 0.05 1.65 Q4 1 0.8176 0.3860 0.4773 11.00000 0.05 1.64 Q5 1 0.2571 0.3845 0.4614 11.00000 0.05 1.57 ; _shelx_res_checksum 93317 _shelx_shelxl_version_number 2016/6 _olex2_exptl_crystal_mounting_method loop _olex2_submission_original_sample_id SM569 _olex2_submission_special_instructions 'No special instructions were received' _oxdiff_exptl_absorpt_empirical_details ; Empirical correction (ABSPACK) includes: - Absorption correction using spherical harmonics - Frame scaling ; _oxdiff_exptl_absorpt_empirical_full_max 8.300 _oxdiff_exptl_absorpt_empirical_full_min 0.555 loop_ _space_group_symop_operation_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_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group I7 I 0.53740(9) 0.38428(2) 0.47071(4) 0.0265(3) Uani 1 1 d . . . . . F13 F 1.0963(12) 0.4471(3) 0.1789(6) 0.0424(12) Uani 1 1 d . . . . . F11 F 0.7302(12) 0.5024(3) 0.1035(5) 0.0456(12) Uani 1 1 d . . . . . F12 F 1.0492(14) 0.5465(3) 0.2492(6) 0.0520(15) Uani 1 1 d . . . . . O17 O 0.2414(11) 0.3186(3) 0.6188(5) 0.0317(11) Uani 1 1 d . . . . . O16 O 0.1610(12) 0.2165(3) 0.6668(6) 0.0363(13) Uani 1 1 d . . . . . O14 O 0.6705(17) 0.5062(3) 0.3862(7) 0.0480(18) Uani 1 1 d . . . . . N15 N 0.2733(13) 0.2574(3) 0.6082(6) 0.0272(13) Uani 1 1 d . . . . . N8 N 0.7680(14) 0.3994(3) 0.3310(6) 0.0278(13) Uani 1 1 d . . . . . C2 C 0.4522(13) 0.2349(4) 0.5222(6) 0.0248(16) Uani 1 1 d . . . . . C1 C 0.5863(15) 0.2805(3) 0.4536(7) 0.0217(13) Uani 1 1 d . . . . . C5 C 0.7828(15) 0.1880(4) 0.3578(7) 0.0273(15) Uani 1 1 d . . . . . H5 H 0.897184 0.171440 0.301334 0.033 Uiso 1 1 calc R . . . . C6 C 0.7515(15) 0.2564(4) 0.3694(7) 0.0235(14) Uani 1 1 d . . . . . H6 H 0.841316 0.286386 0.320583 0.028 Uiso 1 1 calc R . . . . C4 C 0.6518(15) 0.1435(4) 0.4262(7) 0.0244(14) Uani 1 1 d . . . . . H4 H 0.675438 0.096875 0.416080 0.029 Uiso 1 1 calc R . . . . C3 C 0.4867(16) 0.1665(4) 0.5093(8) 0.0290(16) Uani 1 1 d . . . . . H3 H 0.397269 0.135958 0.557207 0.035 Uiso 1 1 calc R . . . . C10 C 0.9196(18) 0.4893(4) 0.2150(8) 0.0335(16) Uani 1 1 d . . . . . C9 C 0.7751(17) 0.4646(4) 0.3226(8) 0.0314(16) Uani 1 1 d . . . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 I7 0.0262(4) 0.0251(4) 0.0293(4) -0.00199(13) 0.0085(2) 0.00315(14) F13 0.044(3) 0.041(3) 0.049(3) 0.006(2) 0.027(2) 0.004(2) F11 0.051(3) 0.050(3) 0.035(2) 0.010(2) 0.005(2) 0.008(2) F12 0.071(4) 0.038(3) 0.052(3) -0.008(2) 0.026(3) -0.021(3) O17 0.028(3) 0.037(3) 0.030(3) -0.003(2) 0.005(2) 0.001(2) O16 0.030(3) 0.047(4) 0.033(3) -0.001(2) 0.009(2) -0.004(2) O14 0.068(5) 0.032(3) 0.053(3) -0.004(3) 0.035(4) 0.007(3) N15 0.021(3) 0.038(3) 0.023(3) 0.003(3) 0.003(2) -0.002(3) N8 0.027(3) 0.029(3) 0.028(3) 0.002(2) 0.007(3) 0.001(3) C2 0.021(4) 0.031(4) 0.021(3) -0.003(2) 0.000(3) -0.001(2) C1 0.023(3) 0.016(3) 0.025(3) -0.001(2) 0.002(3) 0.007(2) C5 0.025(4) 0.031(4) 0.028(3) -0.004(3) 0.009(3) 0.000(3) C6 0.021(3) 0.027(3) 0.023(3) -0.001(3) 0.004(3) -0.002(3) C4 0.022(4) 0.028(4) 0.026(3) -0.003(3) 0.009(3) -0.002(3) C3 0.027(4) 0.025(4) 0.036(4) 0.001(3) 0.010(3) 0.003(3) C10 0.038(4) 0.027(3) 0.035(4) -0.003(3) 0.006(3) -0.003(3) C9 0.031(4) 0.030(4) 0.032(4) -0.006(3) 0.001(3) 0.005(3) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' I I -0.3257 6.8362 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 '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_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N8 I7 C1 89.9(3) . . ? O17 N15 C2 117.8(6) . . ? O16 N15 O17 122.8(7) . . ? O16 N15 C2 119.4(7) . . ? C9 N8 I7 102.8(5) . . ? C1 C2 N15 121.1(7) . . ? C3 C2 N15 117.9(7) . . ? C3 C2 C1 121.0(7) . . ? C2 C1 I7 121.8(6) . . ? C6 C1 I7 119.1(5) . . ? C6 C1 C2 119.0(6) . . ? C6 C5 H5 119.2 . . ? C4 C5 H5 119.2 . . ? C4 C5 C6 121.5(7) . . ? C1 C6 H6 120.5 . . ? C5 C6 C1 119.1(7) . . ? C5 C6 H6 120.5 . . ? C5 C4 H4 119.9 . . ? C3 C4 C5 120.1(7) . . ? C3 C4 H4 119.9 . . ? C2 C3 H3 120.4 . . ? C4 C3 C2 119.3(8) . . ? C4 C3 H3 120.4 . . ? F13 C10 F11 105.7(6) . . ? F13 C10 F12 108.3(7) . . ? F13 C10 C9 115.6(6) . . ? F11 C10 C9 109.6(7) . . ? F12 C10 F11 106.1(6) . . ? F12 C10 C9 111.1(7) . . ? O14 C9 N8 128.1(8) . . ? O14 C9 C10 118.5(7) . . ? N8 C9 C10 113.3(7) . . ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag I7 N8 2.033(7) . ? I7 C1 2.106(6) . ? F13 C10 1.324(10) . ? F11 C10 1.362(10) . ? F12 C10 1.329(9) . ? O17 N15 1.244(9) . ? O16 N15 1.218(9) . ? O14 C9 1.237(9) . ? N15 C2 1.446(9) . ? N8 C9 1.310(11) . ? C2 C1 1.401(10) . ? C2 C3 1.392(12) . ? C1 C6 1.394(11) . ? C5 H5 0.9500 . ? C5 C6 1.388(10) . ? C5 C4 1.378(10) . ? C6 H6 0.9500 . ? C4 H4 0.9500 . ? C4 C3 1.377(12) . ? C3 H3 0.9500 . ? C10 C9 1.520(12) . ? 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_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag I7 N8 C9 O14 1.2(11) . . . . ? I7 N8 C9 C10 -175.4(6) . . . . ? I7 C1 C6 C5 -179.8(5) . . . . ? F13 C10 C9 O14 159.9(8) . . . . ? F13 C10 C9 N8 -23.1(10) . . . . ? F11 C10 C9 O14 -80.8(9) . . . . ? F11 C10 C9 N8 96.1(8) . . . . ? F12 C10 C9 O14 36.1(11) . . . . ? F12 C10 C9 N8 -147.0(7) . . . . ? O17 N15 C2 C1 0.3(9) . . . . ? O17 N15 C2 C3 -179.5(6) . . . . ? O16 N15 C2 C1 -179.6(6) . . . . ? O16 N15 C2 C3 0.5(10) . . . . ? N15 C2 C1 I7 0.0(8) . . . . ? N15 C2 C1 C6 -178.5(6) . . . . ? N15 C2 C3 C4 178.8(7) . . . . ? C2 C1 C6 C5 -1.3(10) . . . . ? C1 C2 C3 C4 -1.0(11) . . . . ? C5 C4 C3 C2 0.6(11) . . . . ? C6 C5 C4 C3 -0.5(11) . . . . ? C4 C5 C6 C1 0.8(11) . . . . ? C3 C2 C1 I7 179.8(5) . . . . ? C3 C2 C1 C6 1.4(10) . . . . ?