#------------------------------------------------------------------------------
#$Date: 2024-02-04 14:16:44 +0200 (Sun, 04 Feb 2024) $
#$Revision: 289565 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/77/7247784.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_7247784
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 thio-oxindoles
;
_journal_issue                   1
_journal_name_full               'Green Chemistry'
_journal_page_first              448
_journal_page_last               455
_journal_paper_doi               10.1039/D3GC03702A
_journal_volume                  26
_journal_year                    2024
_chemical_formula_moiety         'C22 H16 F3 N O'
_chemical_formula_sum            'C22 H16 F3 N O'
_chemical_formula_weight         367.36
_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_Hall           'P 2c -2ac'
_space_group_name_H-M_alt        'P c a 21'
_atom_sites_solution_hydrogens   difmap
_audit_creation_date             2023-02-21
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2023-02-21 deposited with the CCDC.	2023-11-23 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.8883(9)
_cell_length_b                   15.522(2)
_cell_length_c                   16.668(2)
_cell_measurement_reflns_used    4477
_cell_measurement_temperature    298
_cell_measurement_theta_max      24.97
_cell_measurement_theta_min      2.77
_cell_volume                     1782.1(4)
_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
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART APEX2 area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0469
_diffrn_reflns_av_unetI/netI     0.0457
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            11776
_diffrn_reflns_point_group_measured_fraction_full 0.967
_diffrn_reflns_point_group_measured_fraction_max 0.962
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.406
_diffrn_reflns_theta_min         2.774
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_exptl_absorpt_coefficient_mu    0.105
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.5914
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1251 before and 0.0637 after correction.
The Ratio of minimum to maximum transmission is 0.7916.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.369
_exptl_crystal_description       plate
_exptl_crystal_F_000             760
_exptl_crystal_size_max          0.356
_exptl_crystal_size_mid          0.256
_exptl_crystal_size_min          0.098
_refine_diff_density_max         0.109
_refine_diff_density_min         -0.118
_refine_diff_density_rms         0.028
_refine_ls_abs_structure_details
;
 Flack x determined using 1136 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.4(5)
_refine_ls_extinction_coef       0.021(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     309
_refine_ls_number_reflns         3526
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0521
_refine_ls_R_factor_gt           0.0387
_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/[σ²(Fo²)+(0.0413P)²+0.1624P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0883
_refine_ls_wR_factor_ref         0.0965
_reflns_Friedel_coverage         0.860
_reflns_Friedel_fraction_full    0.936
_reflns_Friedel_fraction_max     0.925
_reflns_number_gt                2903
_reflns_number_total             3526
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3gc03702a2.cif
_cod_data_source_block           agml_661_0m
_cod_depositor_comments
'Adding full bibliography for 7247784--7247789.cif.'
_cod_database_code               7247784
_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.
;
_olex2_refinement_description
;
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y, z'
'-x+1/2, y, 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
O1 O 0.2864(3) 0.69823(13) 0.53651(12) 0.0512(5) Uani 1 1 d . . . . .
N1 N 0.4916(4) 0.78458(17) 0.61252(14) 0.0487(6) Uani 1 1 d . . . . .
F3 F 0.1273(5) 0.54591(14) 0.60730(18) 0.1036(9) Uani 1 1 d . . . . .
F2 F 0.3410(5) 0.60449(19) 0.6773(2) 0.1188(11) Uani 1 1 d . . . . .
F1 F 0.0453(6) 0.6171(2) 0.70874(19) 0.1351(14) Uani 1 1 d . . . . .
C17 C 0.7175(4) 0.82445(17) 0.51445(17) 0.0421(7) Uani 1 1 d . . . . .
C11 C 0.4418(4) 0.81349(17) 0.41007(16) 0.0408(6) Uani 1 1 d . . . . .
C5 C 0.6693(4) 0.68790(18) 0.43791(18) 0.0435(7) Uani 1 1 d . . . . .
C16 C 0.4508(5) 0.9014(2) 0.3979(2) 0.0525(8) Uani 1 1 d . . . . .
C6 C 0.7071(5) 0.6158(2) 0.4835(2) 0.0537(8) Uani 1 1 d . . . . .
C3 C 0.4441(4) 0.74866(17) 0.54675(18) 0.0432(6) Uani 1 1 d . . . . .
C4 C 0.5682(4) 0.76751(17) 0.47262(16) 0.0417(6) Uani 1 1 d . . . . .
C12 C 0.3111(4) 0.7654(2) 0.36376(19) 0.0505(7) Uani 1 1 d . . . . .
C22 C 0.6642(4) 0.83153(18) 0.59481(18) 0.0453(7) Uani 1 1 d . . . . .
C18 C 0.8857(5) 0.8628(2) 0.4874(2) 0.0505(7) Uani 1 1 d . . . . .
C13 C 0.2007(5) 0.8053(2) 0.30517(19) 0.0549(8) Uani 1 1 d . . . . .
C15 C 0.3377(5) 0.9407(3) 0.3394(2) 0.0624(9) Uani 1 1 d . . . . .
C1 C 0.1655(6) 0.6158(2) 0.6480(2) 0.0619(9) Uani 1 1 d . . . . .
C14 C 0.2154(5) 0.8922(2) 0.2929(2) 0.0608(9) Uani 1 1 d . . . . .
C20 C 0.9427(5) 0.9181(2) 0.6204(2) 0.0606(9) Uani 1 1 d . . . . .
C19 C 0.9977(5) 0.9104(2) 0.5410(2) 0.0568(8) Uani 1 1 d . . . . .
C21 C 0.7752(5) 0.8775(2) 0.6486(2) 0.0560(8) Uani 1 1 d . . . . .
C2 C 0.1485(5) 0.6965(2) 0.6016(2) 0.0557(8) Uani 1 1 d . . . . .
C10 C 0.7368(6) 0.6897(3) 0.3593(2) 0.0621(9) Uani 1 1 d . . . . .
C8 C 0.8764(5) 0.5491(3) 0.3751(3) 0.0717(11) Uani 1 1 d . . . . .
C7 C 0.8098(6) 0.5468(2) 0.4527(3) 0.0678(10) Uani 1 1 d . . . . .
C9 C 0.8387(6) 0.6202(3) 0.3282(3) 0.0757(12) Uani 1 1 d . . . . .
H18 H 0.930(5) 0.858(2) 0.433(2) 0.059(9) Uiso 1 1 d . . . . .
H21 H 0.734(5) 0.881(2) 0.707(3) 0.061(9) Uiso 1 1 d . . . . .
H20 H 1.025(5) 0.952(2) 0.658(2) 0.068(10) Uiso 1 1 d . . . . .
H19 H 1.127(5) 0.943(2) 0.523(2) 0.074(11) Uiso 1 1 d . . . . .
H2A H 0.184(5) 0.748(2) 0.638(2) 0.068(11) Uiso 1 1 d . . . . .
H12 H 0.301(4) 0.702(2) 0.3726(19) 0.046(8) Uiso 1 1 d . . . . .
H16 H 0.531(5) 0.936(2) 0.428(2) 0.054(9) Uiso 1 1 d . . . . .
H10 H 0.705(5) 0.738(2) 0.327(2) 0.071(11) Uiso 1 1 d . . . . .
H15 H 0.344(6) 0.999(3) 0.333(3) 0.078(12) Uiso 1 1 d . . . . .
H7 H 0.836(7) 0.494(4) 0.485(3) 0.106(15) Uiso 1 1 d . . . . .
H13 H 0.107(6) 0.773(2) 0.269(2) 0.068(10) Uiso 1 1 d . . . . .
H9 H 0.880(6) 0.621(2) 0.274(3) 0.077(12) Uiso 1 1 d . . . . .
H6 H 0.660(5) 0.614(2) 0.539(3) 0.068(11) Uiso 1 1 d . . . . .
H8 H 0.948(6) 0.498(3) 0.352(3) 0.092(13) Uiso 1 1 d . . . . .
H2B H 0.017(6) 0.696(3) 0.577(2) 0.085(13) Uiso 1 1 d . . . . .
H14 H 0.138(6) 0.921(3) 0.253(3) 0.076(12) Uiso 1 1 d . . . . .
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 O1 C2 116.5(2) . . ?
C3 N1 C22 105.1(2) . . ?
C22 C17 C4 107.9(2) . . ?
C18 C17 C4 131.9(3) . . ?
C18 C17 C22 120.1(3) . . ?
C16 C11 C4 122.3(3) . . ?
C16 C11 C12 118.3(3) . . ?
C12 C11 C4 119.4(2) . . ?
C6 C5 C4 122.2(3) . . ?
C6 C5 C10 118.2(3) . . ?
C10 C5 C4 119.4(3) . . ?
C11 C16 C15 120.8(3) . . ?
C11 C16 H16 121(2) . . ?
C15 C16 H16 118(2) . . ?
C5 C6 C7 121.4(4) . . ?
C5 C6 H6 119(2) . . ?
C7 C6 H6 120(2) . . ?
O1 C3 C4 117.3(2) . . ?
N1 C3 O1 124.7(3) . . ?
N1 C3 C4 117.9(2) . . ?
C17 C4 C11 115.1(2) . . ?
C17 C4 C5 109.5(2) . . ?
C17 C4 C3 96.8(2) . . ?
C5 C4 C11 112.1(2) . . ?
C3 C4 C11 108.7(2) . . ?
C3 C4 C5 113.9(2) . . ?
C11 C12 H12 119.2(18) . . ?
C13 C12 C11 120.2(3) . . ?
C13 C12 H12 120.5(18) . . ?
C17 C22 N1 112.2(2) . . ?
C21 C22 N1 126.3(3) . . ?
C21 C22 C17 121.4(3) . . ?
C17 C18 C19 119.0(3) . . ?
C17 C18 H18 123(2) . . ?
C19 C18 H18 118(2) . . ?
C12 C13 H13 123(2) . . ?
C14 C13 C12 120.4(3) . . ?
C14 C13 H13 117(2) . . ?
C16 C15 H15 120(3) . . ?
C14 C15 C16 120.1(4) . . ?
C14 C15 H15 120(3) . . ?
F3 C1 F2 105.5(3) . . ?
F3 C1 F1 106.7(3) . . ?
F3 C1 C2 114.7(3) . . ?
F2 C1 C2 112.3(3) . . ?
F1 C1 F2 107.2(4) . . ?
F1 C1 C2 110.0(3) . . ?
C13 C14 C15 120.2(3) . . ?
C13 C14 H14 121(2) . . ?
C15 C14 H14 118(2) . . ?
C19 C20 C21 120.7(3) . . ?
C19 C20 H20 120(2) . . ?
C21 C20 H20 119(2) . . ?
C18 C19 H19 122(2) . . ?
C20 C19 C18 120.6(3) . . ?
C20 C19 H19 117(2) . . ?
C22 C21 C20 118.2(3) . . ?
C22 C21 H21 120(2) . . ?
C20 C21 H21 122(2) . . ?
O1 C2 C1 110.9(3) . . ?
O1 C2 H2A 105(2) . . ?
O1 C2 H2B 107(2) . . ?
C1 C2 H2A 110(2) . . ?
C1 C2 H2B 106(2) . . ?
H2A C2 H2B 118(3) . . ?
C5 C10 H10 119(2) . . ?
C9 C10 C5 120.4(4) . . ?
C9 C10 H10 121(2) . . ?
C7 C8 C9 119.5(4) . . ?
C7 C8 H8 120(3) . . ?
C9 C8 H8 121(3) . . ?
C6 C7 H7 122(3) . . ?
C8 C7 C6 120.1(4) . . ?
C8 C7 H7 118(3) . . ?
C10 C9 H9 120(2) . . ?
C8 C9 C10 120.4(4) . . ?
C8 C9 H9 120(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
O1 C3 1.350(3) . ?
O1 C2 1.443(4) . ?
N1 C3 1.273(4) . ?
N1 C22 1.426(4) . ?
F3 C1 1.306(4) . ?
F2 C1 1.315(4) . ?
F1 C1 1.308(4) . ?
C17 C4 1.525(4) . ?
C17 C22 1.393(4) . ?
C17 C18 1.378(4) . ?
C11 C16 1.382(4) . ?
C11 C4 1.534(4) . ?
C11 C12 1.402(4) . ?
C5 C6 1.378(5) . ?
C5 C4 1.532(4) . ?
C5 C10 1.390(5) . ?
C16 C15 1.388(5) . ?
C16 H16 0.92(3) . ?
C6 C7 1.383(5) . ?
C6 H6 0.98(4) . ?
C3 C4 1.531(4) . ?
C12 C13 1.384(5) . ?
C12 H12 1.00(3) . ?
C22 C21 1.377(4) . ?
C18 C19 1.392(5) . ?
C18 H18 0.96(4) . ?
C13 C14 1.369(5) . ?
C13 H13 1.02(4) . ?
C15 C14 1.370(5) . ?
C15 H15 0.92(4) . ?
C1 C2 1.476(5) . ?
C14 H14 0.96(4) . ?
C20 C19 1.382(5) . ?
C20 C21 1.397(5) . ?
C20 H20 1.00(4) . ?
C19 H19 1.06(4) . ?
C21 H21 1.02(4) . ?
C2 H2A 1.03(4) . ?
C2 H2B 1.00(4) . ?
C10 C9 1.388(5) . ?
C10 H10 0.95(4) . ?
C8 C7 1.373(6) . ?
C8 C9 1.377(6) . ?
C8 H8 1.01(5) . ?
C7 H7 0.99(5) . ?
C9 H9 0.95(5) . ?
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
O1 C3 C4 C17 179.5(2) . . . . ?
O1 C3 C4 C11 60.1(3) . . . . ?
O1 C3 C4 C5 -65.7(3) . . . . ?
N1 C3 C4 C17 2.6(3) . . . . ?
N1 C3 C4 C11 -116.8(3) . . . . ?
N1 C3 C4 C5 117.5(3) . . . . ?
N1 C22 C21 C20 178.6(3) . . . . ?
F3 C1 C2 O1 -62.5(4) . . . . ?
F2 C1 C2 O1 57.9(4) . . . . ?
F1 C1 C2 O1 177.3(3) . . . . ?
C17 C22 C21 C20 0.7(5) . . . . ?
C17 C18 C19 C20 1.0(5) . . . . ?
C11 C16 C15 C14 -0.1(5) . . . . ?
C11 C12 C13 C14 -1.2(5) . . . . ?
C5 C6 C7 C8 -0.1(5) . . . . ?
C5 C10 C9 C8 -0.9(6) . . . . ?
C16 C11 C4 C17 -5.6(4) . . . . ?
C16 C11 C4 C5 -131.6(3) . . . . ?
C16 C11 C4 C3 101.6(3) . . . . ?
C16 C11 C12 C13 2.7(4) . . . . ?
C16 C15 C14 C13 1.6(5) . . . . ?
C6 C5 C4 C17 83.7(3) . . . . ?
C6 C5 C4 C11 -147.3(3) . . . . ?
C6 C5 C4 C3 -23.4(4) . . . . ?
C6 C5 C10 C9 0.3(5) . . . . ?
C3 O1 C2 C1 -104.0(3) . . . . ?
C3 N1 C22 C17 1.6(3) . . . . ?
C3 N1 C22 C21 -176.5(3) . . . . ?
C4 C17 C22 N1 0.0(3) . . . . ?
C4 C17 C22 C21 178.2(3) . . . . ?
C4 C17 C18 C19 -178.3(3) . . . . ?
C4 C11 C16 C15 178.5(3) . . . . ?
C4 C11 C12 C13 -177.8(3) . . . . ?
C4 C5 C6 C7 -175.7(3) . . . . ?
C4 C5 C10 C9 176.2(3) . . . . ?
C12 C11 C16 C15 -2.1(5) . . . . ?
C12 C11 C4 C17 174.9(3) . . . . ?
C12 C11 C4 C5 48.9(3) . . . . ?
C12 C11 C4 C3 -77.9(3) . . . . ?
C12 C13 C14 C15 -0.9(5) . . . . ?
C22 N1 C3 O1 -179.3(3) . . . . ?
C22 N1 C3 C4 -2.7(3) . . . . ?
C22 C17 C4 C11 113.0(3) . . . . ?
C22 C17 C4 C5 -119.6(3) . . . . ?
C22 C17 C4 C3 -1.3(3) . . . . ?
C22 C17 C18 C19 -1.8(4) . . . . ?
C18 C17 C4 C11 -70.2(4) . . . . ?
C18 C17 C4 C5 57.2(4) . . . . ?
C18 C17 C4 C3 175.5(3) . . . . ?
C18 C17 C22 N1 -177.2(3) . . . . ?
C18 C17 C22 C21 0.9(4) . . . . ?
C19 C20 C21 C22 -1.5(5) . . . . ?
C21 C20 C19 C18 0.7(5) . . . . ?
C2 O1 C3 N1 9.9(4) . . . . ?
C2 O1 C3 C4 -166.7(2) . . . . ?
C10 C5 C6 C7 0.2(5) . . . . ?
C10 C5 C4 C17 -92.0(3) . . . . ?
C10 C5 C4 C11 37.0(4) . . . . ?
C10 C5 C4 C3 160.9(3) . . . . ?
C7 C8 C9 C10 1.0(6) . . . . ?
C9 C8 C7 C6 -0.5(6) . . . . ?
