Copper-catalyzed cyclization reaction: synthesis of trifluoromethylated indolinyl ketones.
Ji, Wangqin; Wu, Hai-Hong; Li, Wenbo; Zhang, Junliang; Chemical communications (Cambridge, England) 57 (2021) 4448–4451; doi:10.1039/d1cc00960e

data_7128049
_publ_section_title
;
 Copper-catalyzed cyclization reaction: synthesis of trifluoromethylated
 indolinyl ketones.
;
_journal_issue                   36
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              4448
_journal_page_last               4451
_journal_paper_doi               10.1039/d1cc00960e
_journal_volume                  57
_journal_year                    2021
_chemical_formula_moiety         'C17 H14 F3 N O'
_chemical_formula_sum            'C17 H14 F3 N O'
_chemical_formula_weight         305.29
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-01-26
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-02-16 deposited with the CCDC.	2021-03-22 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   17.7969(2)
_cell_length_b                   8.47540(10)
_cell_length_c                   19.13530(10)
_cell_measurement_reflns_used    31343
_cell_measurement_temperature    169.99(10)
_cell_measurement_theta_max      74.2730
_cell_measurement_theta_min      4.5900
_cell_volume                     2886.29(5)
_computing_cell_refinement       'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      169.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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    -23.00  48.00   1.00    1.00    --    0.00  19.00 -60.00   71
  2  \w     61.00  87.00   1.00    1.00    --    0.00  19.00 -60.00   26
  3  \w    -73.00 -13.00   1.00    1.00    --    0.00 -77.00 -30.00   60
  4  \w    -21.00  86.00   1.00    1.00    --    0.00  57.00-150.00  107
  5  \w    -23.00   5.00   1.00    1.00    --    0.00  77.00  60.00   28
  6  \w    -30.00  24.00   1.00    1.00    --    0.00  77.00 -30.00   54
  7  \w    -22.00  14.00   1.00    1.00    --    0.00  57.00 150.00   36
  8  \w     31.00  85.00   1.00    1.00    --    0.00  77.00  60.00   54
  9  \w     45.00  85.00   1.00    1.00    --    0.00  77.00 -30.00   40
 10  \w    -23.00  37.00   1.00    1.00    --    0.00  19.00  60.00   60
 11  \w     29.00  86.00   1.00    1.00    --    0.00  57.00 150.00   57
 12  \w     50.00  82.00   1.00    1.00    --    0.00  38.00  90.00   32
 13  \w    -19.00  44.00   1.00    1.00    --    0.00  38.00  90.00   63
 14  \w    122.00 184.00   1.00    1.00    --   95.80  77.00 138.28   62
 15  \w     66.00  92.00   1.00    1.00    --   95.80  77.00 138.28   26
 16  \w     67.00  93.00   1.00    1.00    --   95.80  71.00  33.64   26
 17  \w     94.00 185.00   1.00    1.00    --   95.80  78.00  75.17   91
 18  \w     65.00  91.00   1.00    1.00    --   95.80  78.00  75.17   26
 19  \w    153.00 184.00   1.00    1.00    --   95.80  58.00 -98.87   31
 20  \w     71.00  97.00   1.00    1.00    --   95.80  59.00-148.74   26
 21  \w    147.00 172.00   1.00    1.00    --   95.80  61.00-180.00   25
 22  \w     71.00  96.00   1.00    1.00    --   95.80  61.00-180.00   25
 23  \w     75.00 101.00   1.00    1.00    --   95.80  45.00  90.00   26
 24  \w     63.00  88.00   1.00    1.00    --   95.80  82.00-180.00   25
 25  \w     65.00  90.00   1.00    1.00    --   95.80  77.00 120.00   25
 26  \w    107.00 177.00   1.00    1.00    --   95.80  77.00 120.00   70
 27  \w     63.00  88.00   1.00    1.00    --   95.80  82.00-150.00   25
 28  \w     65.00  90.00   1.00    1.00    --   95.80  77.00 -30.00   25
 29  \w     71.00  97.00   1.00    1.00    --   95.80  61.00 -30.00   26
 30  \w    120.00 184.00   1.00    1.00    --   95.80  61.00 -30.00   64
 31  \w    144.00 184.00   1.00    1.00    --   95.80  65.00   2.32   40
 32  \w     82.00 127.00   1.00    1.00    --   95.80 -82.00 150.00   45
 33  \w     31.00  71.00   1.00    1.00    --   95.80 -82.00 150.00   40
 34  \w     70.00  96.00   1.00    1.00    --   95.80  65.00   2.32   26
 35  \w     71.00  96.00   1.00    1.00    --   95.80  58.00 -98.87   25
 36  \w     65.00  90.00   1.00    1.00    --   95.80  77.00 -90.00   25
 37  \w     65.00  91.00   1.00    1.00    --   95.80  77.00  60.00   26
 38  \w     54.00 128.00   1.00    1.00    --   95.80 -82.00-120.00   74
 39  \w     64.00  90.00   1.00    1.00    --   95.80  82.00   0.00   26
 40  \w    160.00 185.00   1.00    1.00    --   95.80  82.00   0.00   25
 41  \w      6.00 128.00   1.00    1.00    --   95.80 -82.00 -60.00  122
 42  \w     63.00  89.00   1.00    1.00    --   95.80  82.00-120.00   26
 43  \w     71.00 184.00   1.00    1.00    --   95.80  59.00-128.88  113
 44  \w    127.00 176.00   1.00    1.00    --   95.80  82.00  30.00   49
 45  \w     64.00  90.00   1.00    1.00    --   95.80  82.00  30.00   26
 46  \w     63.00  88.00   1.00    1.00    --   95.80  82.00 -90.00   25
 47  \w     63.00  88.00   1.00    1.00    --   95.80  82.00 -60.00   25
 48  \w     71.00 127.00   1.00    1.00    --   95.80  61.00 120.00   56
 49  \w     24.00  49.00   1.00    1.00    --   95.80 -82.00-120.00   25
 50  \w     76.00 184.00   1.00    1.00    --   95.80  45.00-150.00  108
 51  \w     71.00 100.00   1.00    1.00    --   95.80  61.00  30.00   29
 52  \w     71.00  97.00   1.00    1.00    --   95.80  61.00  60.00   26
 53  \w    120.00 156.00   1.00    1.00    --   95.80  61.00  60.00   36
 54  \w     65.00  91.00   1.00    1.00    --   95.80  77.00   0.00   26
 55  \w     63.00  89.00   1.00    1.00    --   95.80  82.00 -30.00   26
 56  \w    156.00 181.00   1.00    1.00    --   95.80  82.00 -30.00   25
 57  \w    145.00 178.00   1.00    1.00    --   95.80  76.00 -64.90   33
 58  \w    124.00 167.00   1.00    1.00    --   95.80  45.00   0.00   43
 59  \w     71.00 124.00   1.00    1.00    --   95.80  61.00 150.00   53
 60  \w     66.00  92.00   1.00    1.00    --   95.80  77.00 -60.00   26
 61  \w     65.00  91.00   1.00    1.00    --   95.80  77.00-120.00   26
 62  \w     65.00  91.00   1.00    1.00    --   95.80  77.00  90.00   26
 63  \w     66.00  92.00   1.00    1.00    --   95.80  75.00  30.92   26
 64  \w     75.00 112.00   1.00    1.00    --   95.80  45.00   0.00   37
 65  \w     75.00 173.00   1.00    1.00    --   95.80  45.00 -60.00   98
 66  \w    160.00 185.00   1.00    1.00    --   95.80  77.00-180.00   25
 67  \w     75.00 182.00   1.00    1.00    --   95.80  45.00 -90.00  107
 68  \w     63.00  88.00   1.00    1.00    --   95.80  82.00  60.00   25
 69  \w     65.00  90.00   1.00    1.00    --   95.80  77.00-180.00   25
 70  \w     64.00  90.00   1.00    1.00    --   95.80  80.00 142.46   26
 71  \w     65.00  90.00   1.00    1.00    --   95.80  76.00 -64.90   25
 72  \w     72.00 106.00   1.00    1.00    --   95.80  55.00-130.33   34
 73  \w    142.00 173.00   1.00    1.00    --   95.80  32.00  37.49   31
 74  \w     13.00 127.00   1.00    1.00    --   95.80 -82.00  30.00  114
 75  \w     34.00 126.00   1.00    1.00    --   95.80 -82.00  90.00   92
 76  \w     76.00 101.00   1.00    1.00    --   95.80  32.00  37.49   25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa dual home/near'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0623294000
_diffrn_orient_matrix_UB_12      0.1236941000
_diffrn_orient_matrix_UB_13      -0.0109389000
_diffrn_orient_matrix_UB_21      0.0120048000
_diffrn_orient_matrix_UB_22      -0.0092284000
_diffrn_orient_matrix_UB_23      -0.0796180000
_diffrn_orient_matrix_UB_31      -0.0588165000
_diffrn_orient_matrix_UB_32      -0.1329762000
_diffrn_orient_matrix_UB_33      -0.0046411000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0768
_diffrn_reflns_av_unetI/netI     0.0199
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            64042
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.074
_diffrn_reflns_theta_max         67.074
_diffrn_reflns_theta_min         4.622
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.972
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.11153
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.32a (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    1.405
_exptl_crystal_description       block
_exptl_crystal_F_000             1264
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.218
_refine_diff_density_min         -0.220
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         2568
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.082
_refine_ls_R_factor_all          0.0377
_refine_ls_R_factor_gt           0.0360
_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^)+(0.0439P)^2^+1.0938P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0929
_refine_ls_wR_factor_ref         0.0942
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2441
_reflns_number_total             2568
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1cc00960e2.cif
_cod_data_source_block           exp_1744
_cod_depositor_comments          'Adding full bibliography for 7128049.cif.'
_cod_database_code               7128049
_shelx_shelxl_version_number     2016/6
_reflns_odcompleteness_completeness 99.93
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C7(H7), C8(H8)
2.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C17(H17), C16(H16), C4(H4), C13(H13), C2(H2), C3(H3), C15(H15),
 C14(H14)
2.c Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C)
;
_shelx_res_checksum              81650
_shelx_hkl_checksum              23410
_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 6.496
_oxdiff_exptl_absorpt_empirical_full_min 0.456