#------------------------------------------------------------------------------ #$Date: 2023-11-24 02:38:02 +0200 (Fri, 24 Nov 2023) $ #$Revision: 287767 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/24/77/7247786.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_7247786 loop_ _publ_author_name 'Lamba, Manisha' 'Singh, Prasoon Raj' 'Bhatt, Shubham' 'Goswami, Avijit' _publ_section_title ; Metal- and Additive-Free TfOH Catalyzed Chemoselective O- and S-Trifluoroethylation of Oxindoles, Isoindolines and Thioxindoles ; _journal_name_full 'Green Chemistry' _journal_paper_doi 10.1039/D3GC03702A _journal_year 2023 _chemical_formula_moiety 'C10 H6 Br F3 N O' _chemical_formula_sum 'C10 H6 Br F3 N O' _chemical_formula_weight 293.07 _space_group_crystal_system monoclinic _space_group_IT_number 5 _space_group_name_Hall 'C 2y' _space_group_name_H-M_alt 'C 1 2 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary dual _audit_creation_date 2023-06-13 _audit_creation_method ; Olex2 1.5 (compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498) ; _audit_update_record ; 2023-06-13 deposited with the CCDC. 2023-11-23 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 113.89(3) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 17.093(12) _cell_length_b 10.057(10) _cell_length_c 6.991(4) _cell_measurement_reflns_used 2839 _cell_measurement_temperature 298 _cell_volume 1098.8(15) _computing_cell_refinement 'SAINT V8.40B (?, 2016)' _computing_data_reduction 'SAINT V8.40B (?, 2016)' _computing_molecular_graphics 'Olex2 1.5 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 1.5 (Dolomanov et al., 2009)' _computing_structure_refinement 'SHELXL 2018/3 (Sheldrick, 2015)' _computing_structure_solution 'SHELXT 2018/2 (Sheldrick, 2018)' _diffrn_ambient_temperature 298.00 _diffrn_detector_area_resol_mean 7.9 _diffrn_detector_type 'CCD area detector' _diffrn_measured_fraction_theta_full 0.962 _diffrn_measured_fraction_theta_max 0.955 _diffrn_measurement_device 'three-circle diffractometer' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0522 _diffrn_reflns_av_unetI/netI 0.0635 _diffrn_reflns_Laue_measured_fraction_full 0.962 _diffrn_reflns_Laue_measured_fraction_max 0.955 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_number 5500 _diffrn_reflns_point_group_measured_fraction_full 0.947 _diffrn_reflns_point_group_measured_fraction_max 0.930 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 26.492 _diffrn_reflns_theta_min 2.408 _exptl_absorpt_coefficient_mu 3.759 _exptl_absorpt_correction_T_max 0.7454 _exptl_absorpt_correction_T_min 0.4913 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details SADABS-2016/2 _exptl_crystal_colour yellow _exptl_crystal_colour_primary yellow _exptl_crystal_density_diffrn 1.772 _exptl_crystal_description block _exptl_crystal_F_000 572 _exptl_crystal_size_max 0.215 _exptl_crystal_size_mid 0.123 _exptl_crystal_size_min 0.105 _refine_diff_density_max 0.301 _refine_diff_density_min -0.238 _refine_diff_density_rms 0.053 _refine_ls_abs_structure_details ; Flack x determined using 693 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). ; _refine_ls_abs_structure_Flack 0.076(11) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 0.986 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 145 _refine_ls_number_reflns 2145 _refine_ls_number_restraints 1 _refine_ls_restrained_S_all 0.985 _refine_ls_R_factor_all 0.0497 _refine_ls_R_factor_gt 0.0421 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0666P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1070 _refine_ls_wR_factor_ref 0.1132 _reflns_Friedel_coverage 0.841 _reflns_Friedel_fraction_full 0.930 _reflns_Friedel_fraction_max 0.902 _reflns_number_gt 1790 _reflns_number_total 2145 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d3gc03702a2.cif _cod_data_source_block momo_a _cod_database_code 7247786 _shelx_shelxl_version_number 2018/3 _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. ; _shelx_estimated_absorpt_t_max 0.694 _shelx_estimated_absorpt_t_min 0.499 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups, All C(H,H) groups 2.a Secondary CH2 refined with riding coordinates: C2(H2A,H2B) 2.b Aromatic/amide H refined with riding coordinates: C9(H9), C7(H7), C8(H8), C5(H5) ; _shelx_res_file ; TITL momo_a.res in C2 momo_a.res created by SHELXL-2018/3 at 10:57:01 on 13-Jun-2023 CELL 0.71073 17.0933 10.057 6.9912 90 113.894 90 ZERR 4 0.0124 0.0096 0.0039 0 0.025 0 LATT -7 SYMM -X,+Y,-Z SFAC C H Br F N O UNIT 40 24 4 12 4 4 L.S. 4 PLAN 1 0 0 SIZE 0.105 0.215 0.123 TEMP 24.85 CONF HTAB BOND $H MORE -1 fmap 2 acta REM REM REM WGHT 0.066600 FVAR 0.96787 BR1 3 0.607476 0.969350 0.857432 11.00000 0.08957 0.07177 = 0.10447 -0.00472 0.03704 -0.01104 F1 4 0.304713 0.032605 0.554803 11.00000 0.08267 0.10139 = 0.13106 -0.01291 0.03333 -0.03222 O2 6 0.412786 0.341278 0.662548 11.00000 0.03725 0.07846 = 0.07191 -0.00353 0.01465 -0.00644 F3 4 0.273511 0.210135 0.370915 11.00000 0.08050 0.15243 = 0.07130 0.00485 0.00498 -0.03949 F4 4 0.273680 0.210435 0.676662 11.00000 0.08174 0.15064 = 0.11593 -0.03507 0.06259 -0.03944 N1 5 0.562652 0.322837 0.813341 11.00000 0.03997 0.07424 = 0.07954 0.00048 0.01603 -0.00231 C6 1 0.493719 0.393492 0.743408 11.00000 0.03347 0.07142 = 0.04826 -0.00295 0.01391 -0.00503 C10 1 0.592664 0.557911 0.842841 11.00000 0.03717 0.07866 = 0.03563 0.00028 0.01559 -0.00062 C9 1 0.625018 0.685061 0.875388 11.00000 0.03914 0.08198 = 0.04413 0.00077 0.01645 -0.00030 AFIX 43 H9 2 0.683699 0.700404 0.934533 11.00000 -1.20000 AFIX 0 C7 1 0.446728 0.640243 0.696378 11.00000 0.04007 0.08703 = 0.04747 -0.00050 0.01581 0.00164 AFIX 43 H7 2 0.388097 0.624440 0.637573 11.00000 -1.20000 AFIX 0 C8 1 0.479081 0.771104 0.728859 11.00000 0.05464 0.07076 = 0.06286 0.00205 0.02168 0.00809 AFIX 43 H8 2 0.442137 0.843596 0.691950 11.00000 -1.20000 AFIX 0 C1 1 0.315160 0.164972 0.565868 11.00000 0.05857 0.09117 = 0.06873 -0.00977 0.02482 -0.02533 C2 1 0.407640 0.199760 0.657627 11.00000 0.04183 0.08268 = 0.08305 -0.00531 0.01781 -0.01058 AFIX 23 H2A 2 0.435412 0.163789 0.797907 11.00000 -1.20000 H2B 2 0.435519 0.163644 0.572689 11.00000 -1.20000 AFIX 0 C3 1 0.503477 0.537703 0.753267 11.00000 0.03571 0.08143 = 0.03839 -0.00081 0.01455 0.00085 C4 1 0.567108 0.789776 0.816957 11.00000 0.06061 0.07159 = 0.05012 -0.00252 0.02412 -0.00425 C5 1 0.632877 0.422801 0.881924 11.00000 0.03813 0.06680 = 0.08514 -0.00074 0.01454 0.00152 AFIX 43 H5 2 0.691221 0.404612 0.938803 11.00000 -1.20000 AFIX 0 HKLF 4 REM momo_a.res in C2 REM wR2 = 0.1132, GooF = S = 0.986, Restrained GooF = 0.985 for all data REM R1 = 0.0421 for 1790 Fo > 4sig(Fo) and 0.0497 for all 2145 data REM 145 parameters refined using 1 restraints END WGHT 0.0666 0.0000 REM No hydrogen bonds found for HTAB generation REM Highest difference peak 0.301, deepest hole -0.238, 1-sigma level 0.053 Q1 1 0.5525 0.9749 0.7884 11.00000 0.05 0.30 ; _shelx_res_checksum 52895 _olex2_submission_special_instructions 'No special instructions were received' loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y, -z' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z' 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 Br1 Br 0.60748(4) 0.96935(6) 0.85743(10) 0.0893(3) Uani 1 1 d . . . . . F1 F 0.3047(3) 0.0326(6) 0.5548(9) 0.1083(15) Uani 1 1 d . . . . . O2 O 0.4128(2) 0.3413(5) 0.6625(6) 0.0650(11) Uani 1 1 d . . . . . F3 F 0.2735(3) 0.2101(6) 0.3709(6) 0.1097(17) Uani 1 1 d . . . . . F4 F 0.2737(3) 0.2104(6) 0.6767(8) 0.1088(17) Uani 1 1 d . . . . . N1 N 0.5627(3) 0.3228(6) 0.8133(8) 0.0672(13) Uani 1 1 d . . . . . C6 C 0.4937(3) 0.3935(7) 0.7434(8) 0.0519(12) Uani 1 1 d . . . . . C10 C 0.5927(3) 0.5579(7) 0.8428(7) 0.0502(12) Uani 1 1 d . . . . . C9 C 0.6250(3) 0.6851(7) 0.8754(7) 0.0552(12) Uani 1 1 d . . . . . H9 H 0.683699 0.700404 0.934533 0.066 Uiso 1 1 calc R U . . . C7 C 0.4467(3) 0.6402(7) 0.6964(7) 0.0588(13) Uani 1 1 d . . . . . H7 H 0.388097 0.624440 0.637573 0.071 Uiso 1 1 calc R U . . . C8 C 0.4791(3) 0.7711(7) 0.7289(8) 0.0634(12) Uani 1 1 d . . . . . H8 H 0.442137 0.843596 0.691950 0.076 Uiso 1 1 calc R U . . . C1 C 0.3152(4) 0.1650(8) 0.5659(10) 0.0731(17) Uani 1 1 d . . . . . C2 C 0.4076(4) 0.1998(8) 0.6576(10) 0.0716(16) Uani 1 1 d . . . . . H2A H 0.435412 0.163789 0.797907 0.086 Uiso 1 1 calc R U . . . H2B H 0.435519 0.163644 0.572689 0.086 Uiso 1 1 calc R U . . . C3 C 0.5035(3) 0.5377(7) 0.7533(7) 0.0520(13) Uani 1 1 d . . . . . C4 C 0.5671(4) 0.7898(7) 0.8170(7) 0.0602(13) Uani 1 1 d . . . . . C5 C 0.6329(4) 0.4228(7) 0.8819(10) 0.0667(14) Uani 1 1 d . . . . . H5 H 0.691221 0.404612 0.938803 0.080 Uiso 1 1 calc R U . . . 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 Br1 0.0896(5) 0.0718(4) 0.1045(5) -0.0047(4) 0.0370(4) -0.0110(4) F1 0.083(3) 0.101(4) 0.131(3) -0.013(3) 0.033(2) -0.032(3) O2 0.0373(16) 0.078(3) 0.072(2) -0.0035(19) 0.0147(16) -0.0064(19) F3 0.080(3) 0.152(5) 0.071(2) 0.005(2) 0.0050(19) -0.039(3) F4 0.082(3) 0.151(5) 0.116(3) -0.035(3) 0.063(2) -0.039(3) N1 0.040(2) 0.074(3) 0.080(3) 0.000(2) 0.016(2) -0.002(2) C6 0.033(2) 0.071(4) 0.048(2) -0.003(2) 0.0139(18) -0.005(2) C10 0.037(2) 0.079(4) 0.036(2) 0.000(2) 0.0156(17) -0.001(2) C9 0.039(2) 0.082(4) 0.044(2) 0.001(2) 0.0165(17) 0.000(2) C7 0.040(2) 0.087(4) 0.047(2) 0.000(3) 0.0158(19) 0.002(2) C8 0.055(3) 0.071(3) 0.063(2) 0.002(3) 0.022(2) 0.008(3) C1 0.059(3) 0.091(5) 0.069(3) -0.010(3) 0.025(3) -0.025(3) C2 0.042(3) 0.083(5) 0.083(4) -0.005(3) 0.018(3) -0.011(3) C3 0.036(2) 0.081(4) 0.038(2) -0.001(2) 0.0146(16) 0.001(2) C4 0.061(3) 0.072(4) 0.050(2) -0.003(2) 0.024(2) -0.004(3) C5 0.038(2) 0.067(4) 0.085(3) -0.001(3) 0.015(2) 0.002(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' Br Br -0.2901 2.4595 '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_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C6 O2 C2 115.8(5) . . ? C6 N1 C5 104.1(6) . . ? O2 C6 C3 118.5(5) . . ? N1 C6 O2 124.0(6) . . ? N1 C6 C3 117.4(5) . . ? C9 C10 C3 119.9(7) . . ? C9 C10 C5 133.6(5) . . ? C3 C10 C5 106.5(6) . . ? C10 C9 H9 121.1 . . ? C10 C9 C4 117.7(5) . . ? C4 C9 H9 121.1 . . ? C8 C7 H7 120.9 . . ? C3 C7 H7 120.9 . . ? C3 C7 C8 118.3(5) . . ? C7 C8 H8 120.6 . . ? C4 C8 C7 118.8(6) . . ? C4 C8 H8 120.6 . . ? F1 C1 C2 110.6(7) . . ? F3 C1 F1 106.0(5) . . ? F3 C1 C2 113.2(5) . . ? F4 C1 F1 106.6(5) . . ? F4 C1 F3 106.8(6) . . ? F4 C1 C2 113.2(5) . . ? O2 C2 C1 106.8(6) . . ? O2 C2 H2A 110.4 . . ? O2 C2 H2B 110.4 . . ? C1 C2 H2A 110.4 . . ? C1 C2 H2B 110.4 . . ? H2A C2 H2B 108.6 . . ? C10 C3 C6 104.3(5) . . ? C7 C3 C6 133.3(5) . . ? C7 C3 C10 122.4(7) . . ? C9 C4 Br1 120.1(4) . . ? C8 C4 Br1 117.0(5) . . ? C8 C4 C9 122.9(6) . . ? N1 C5 C10 107.7(5) . . ? N1 C5 H5 126.2 . . ? C10 C5 H5 126.2 . . ? 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 Br1 C4 1.913(7) . ? F1 C1 1.341(10) . ? O2 C6 1.370(6) . ? O2 C2 1.426(9) . ? F3 C1 1.336(8) . ? F4 C1 1.325(8) . ? N1 C6 1.291(8) . ? N1 C5 1.488(9) . ? C6 C3 1.458(8) . ? C10 C9 1.375(10) . ? C10 C3 1.409(7) . ? C10 C5 1.497(10) . ? C9 H9 0.9300 . ? C9 C4 1.389(9) . ? C7 H7 0.9300 . ? C7 C8 1.410(10) . ? C7 C3 1.360(9) . ? C8 H8 0.9300 . ? C8 C4 1.388(8) . ? C1 C2 1.487(8) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C5 H5 0.9300 . ? 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 F1 C1 C2 O2 179.7(6) . . . . ? O2 C6 C3 C10 179.9(4) . . . . ? O2 C6 C3 C7 -0.1(9) . . . . ? F3 C1 C2 O2 61.0(8) . . . . ? F4 C1 C2 O2 -60.7(7) . . . . ? N1 C6 C3 C10 0.3(7) . . . . ? N1 C6 C3 C7 -179.7(5) . . . . ? C6 O2 C2 C1 179.8(4) . . . . ? C6 N1 C5 C10 0.9(7) . . . . ? C10 C9 C4 Br1 -180.0(3) . . . . ? C10 C9 C4 C8 0.2(7) . . . . ? C9 C10 C3 C6 180.0(5) . . . . ? C9 C10 C3 C7 0.0(6) . . . . ? C9 C10 C5 N1 179.7(5) . . . . ? C7 C8 C4 Br1 180.0(4) . . . . ? C7 C8 C4 C9 -0.2(7) . . . . ? C8 C7 C3 C6 -180.0(6) . . . . ? C8 C7 C3 C10 0.0(7) . . . . ? C2 O2 C6 N1 -0.3(8) . . . . ? C2 O2 C6 C3 -179.9(5) . . . . ? C3 C10 C9 C4 -0.1(6) . . . . ? C3 C10 C5 N1 -0.8(5) . . . . ? C3 C7 C8 C4 0.1(7) . . . . ? C5 N1 C6 O2 179.7(5) . . . . ? C5 N1 C6 C3 -0.7(7) . . . . ? C5 C10 C9 C4 179.4(5) . . . . ? C5 C10 C3 C6 0.3(5) . . . . ? C5 C10 C3 C7 -179.7(5) . . . . ?