The B(C<sub>6</sub>F<sub>5</sub>)<sub>3</sub>·H<sub>2</sub>O promoted synthesis of fluoroalkylated 3,3',3''-trisindolylmethanes from fluorocarboxylic acids and indoles.
Xu, Xin; Gao, Dandan; Wang, Jiahua; Tang, Xiang-Ying; Wang, Long; Organic & biomolecular chemistry 21 (2023) 1478–1486; doi:10.1039/d2ob02241a

data_7159092
_publ_section_title
;
 The B(C<sub>6</sub>F<sub>5</sub>)<sub>3</sub>&#xb7;H<sub>2</sub>O
 promoted synthesis of fluoroalkylated 3,3',3''-trisindolylmethanes from
 fluorocarboxylic acids and indoles.
;
_journal_issue                   7
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              1478
_journal_page_last               1486
_journal_paper_doi               10.1039/d2ob02241a
_journal_volume                  21
_journal_year                    2023
_chemical_formula_moiety         'C26 H21 F2 N3 O'
_chemical_formula_sum            'C26 H21 F2 N3 O'
_chemical_formula_weight         429.46
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2022-10-17
_audit_creation_method
;
Olex2 1.3
(compiled 2020.06.28 svn.raecde09e for OlexSys, GUI svn.r6132)
;
_audit_update_record
;
2022-10-17 deposited with the CCDC.	2023-01-09 downloaded from the CCDC.
;
_cell_angle_alpha                96.9030(10)
_cell_angle_beta                 93.4250(10)
_cell_angle_gamma                106.0050(10)
_cell_formula_units_Z            4
_cell_length_a                   9.31770(10)
_cell_length_b                   11.85180(10)
_cell_length_c                   19.9301(2)
_cell_measurement_reflns_used    38249
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      73.5880
_cell_measurement_theta_min      2.2490
_cell_volume                     2090.29(4)
_computing_cell_refinement       'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.974
_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 -19.00   0.50    0.50    --    0.00 -21.00  86.00  138
  2  \w     32.00  77.00   0.50    0.50    --    0.00  21.00-107.00   90
  3  \w     15.00  59.00   0.50    0.50    --   94.60 -21.00  86.00   88
  4  \w    106.00 131.00   0.50    0.50    --   94.60  21.00-107.00   50
  5  \w     -8.00  17.00   0.50    0.50    --    0.00 -21.00  86.00   50
  6  \w    -29.00  30.00   0.50    0.50    --    0.00 -82.00-180.00  118
  7  \w      4.00  63.00   0.50    0.50    --   28.00  72.00 -33.65  118
  8  \w     76.00 103.00   0.50    0.50    --   28.00  72.00 -33.65   54
  9  \w    -42.00  55.00   0.50    0.50    --   36.00 -48.00-171.32  194
 10  \w     19.00  52.00   0.50    0.50    --   44.00  72.00  98.14   66
 11  \w     87.00 113.00   0.50    0.50    --   44.00  72.00  98.14   52
 12  \w     21.00  47.00   0.50    0.50    --   48.00  72.00  16.93   52
 13  \w     66.00  92.00   0.50    0.50    --   48.00  72.00  16.93   52
 14  \w     70.00  97.00   0.50    0.50    --   52.00  72.00-138.09   54
 15  \w     25.00  62.00   0.50    0.50    --   52.00  72.00-138.09   74
 16  \w     29.00  61.00   0.50    0.50    --   56.00  73.00 134.37   64
 17  \w    116.00 143.00   0.50    0.50    --   56.00  74.00 169.80   54
 18  \w     31.00  60.00   0.50    0.50    --   56.00  74.00 169.80   58
 19  \w     32.00  57.00   0.50    0.50    --   60.00  74.00 -77.28   50
 20  \w     36.00  74.00   0.50    0.50    --   64.00  75.00  16.28   76
 21  \w     36.00  73.00   0.50    0.50    --   64.00  75.00  77.29   74
 22  \w     45.00  76.00   0.50    0.50    --   72.00  74.00 -54.74   62
 23  \w     45.00  77.00   0.50    0.50    --   72.00  71.00 -88.93   64
 24  \w    104.00 161.00   0.50    0.50    --   72.00  75.00 146.01  114
 25  \w     44.00  79.00   0.50    0.50    --   72.00  75.00 146.01   70
 26  \w     45.00  80.00   0.50    0.50    --   72.00  73.00 -21.62   70
 27  \w     48.00  75.00   0.50    0.50    --   76.00  75.00 102.06   54
 28  \w     48.00  80.00   0.50    0.50    --   76.00  74.00  80.89   64
 29  \w     48.00  79.00   0.50    0.50    --   76.00  75.00 161.84   62
 30  \w     49.00  76.00   0.50    0.50    --   76.00  72.00-137.96   54
 31  \w    135.00 165.00   0.50    0.50    --   76.00  75.00-170.76   60
 32  \w     49.00  83.00   0.50    0.50    --   76.00  75.00-170.76   68
 33  \w     49.00  74.00   0.50    0.50    --   76.00  75.00  23.37   50
 34  \w    138.00 171.00   0.50    0.50    --   84.00  74.00 -37.74   66
 35  \w     58.00 135.00   0.50    0.50    --   84.00  74.00 -37.74  154
 36  \w      6.00 118.00   0.50    0.50    --   94.60 -61.00  90.00  224
 37  \w      5.00  31.00   0.50    0.50    --   94.60 -82.00 -30.00   52
 38  \w     55.00 124.00   0.50    0.50    --   94.60 -82.00-180.00  138
 39  \w      5.00 126.00   0.50    0.50    --   94.60 -82.00  90.00  242
 40  \w     67.00 116.00   0.50    0.50    --   94.60  75.00-112.96   98
 41  \w     72.00 167.00   0.50    0.50    --   94.60  55.00  27.83  190
 42  \w     81.00 175.00   0.50    0.50    --   94.60  45.00 -60.00  188
 43  \w     14.00  39.00   0.50    0.50    --   94.60 -82.00-180.00   50
 44  \w      6.00 105.00   0.50    0.50    --   94.60 -61.00 -30.00  198
 45  \w     73.00 116.00   0.50    0.50    --   94.60  61.00  90.00   86
 46  \w     72.00 162.00   0.50    0.50    --   94.60  61.00 -60.00  180
 47  \w     72.00 178.00   0.50    0.50    --   94.60  61.00   0.00  212
 48  \w     59.00 120.00   0.50    0.50    --   94.60 -77.00-150.00  122
 49  \w     32.00  57.00   0.50    0.50    --   94.60 -77.00-150.00   50
 50  \w    120.00 149.00   0.50    0.50    --   94.60  61.00  90.00   58
 51  \w     71.00 172.00   0.50    0.50    --   94.60  61.00-180.00  202
 52  \w     72.00 130.00   0.50    0.50    --   94.60  61.00 150.00  116
 53  \w    137.00 183.00   0.50    0.50    --   94.60  66.00  39.75   92
 54  \w     69.00 108.00   0.50    0.50    --   94.60  66.00  39.75   78
 55  \w    154.00 180.00   0.50    0.50    --   94.60  61.00-120.00   52
 56  \w     21.00 116.00   0.50    0.50    --   94.60 -82.00 -90.00  190
 57  \w     73.00 143.00   0.50    0.50    --   94.60  64.00 127.51  140
 58  \w    146.00 178.00   0.50    0.50    --   94.60  64.00 127.51   64
 59  \w     71.00 141.00   0.50    0.50    --   94.60  61.00-120.00  140
 60  \w     68.00 146.00   0.50    0.50    --   94.60  72.00-170.93  156
 61  \w     67.00 118.00   0.50    0.50    --   94.60 -82.00 -30.00  102
 62  \w     79.00 174.00   0.50    0.50    --   94.60  77.00  90.00  190
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1637627000
_diffrn_orient_matrix_UB_12      -0.0735753000
_diffrn_orient_matrix_UB_13      -0.0217861000
_diffrn_orient_matrix_UB_21      -0.0479019000
_diffrn_orient_matrix_UB_22      0.1148961000
_diffrn_orient_matrix_UB_23      0.0039402000
_diffrn_orient_matrix_UB_31      0.0274941000
_diffrn_orient_matrix_UB_32      0.0071078000
_diffrn_orient_matrix_UB_33      -0.0750363000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0232
_diffrn_reflns_av_unetI/netI     0.0119
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            52397
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.993
_diffrn_reflns_theta_min         2.244
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.798
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.75558
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.28b (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.365
_exptl_crystal_description       block
_exptl_crystal_F_000             896
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.722
_refine_diff_density_min         -0.538
_refine_diff_density_rms         0.039
_refine_ls_extinction_coef       0.00259(16)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     578
_refine_ls_number_reflns         8275
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.009
_refine_ls_R_factor_all          0.0389
_refine_ls_R_factor_gt           0.0376
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0390P)^2^+1.0952P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0909
_refine_ls_wR_factor_ref         0.0918
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7882
_reflns_number_total             8275
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ob02241a2.cif
_cod_data_source_block           20211011_xx1008
_cod_depositor_comments
'Adding full bibliography for 7159091--7159092.cif.'
_cod_database_code               7159092
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.924
_shelx_estimated_absorpt_t_min   0.844
_reflns_odcompleteness_completeness 99.65
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2.a Ternary CH refined with riding coordinates:
 C00T(H00T), C00Z(H00Z), C017(H017), C01N(H01S)
2.b Secondary CH2 refined with riding coordinates:
 C00N(H00B,H00C), C011(H01B,H01E)
2.c Aromatic/amide H refined with riding coordinates:
 N006(H006), N008(H008), N009(H009), N00A(H00A), N00B(H00D), N00C(H00E),
 C00M(H00M), C00R(H00R), C00S(H00S), C00W(H00W), C010(H010), C013(H013),
 C015(H015), C016(H016), C018(H018), C019(H019), C01A(H01A), C01B(H01F),
 C01C(H01C), C01D(H01D), C01E(H01G), C01F(H01H), C01G(H01I), C01H(H01K),
 C01I(H01M), C01J(H01J), C01K(H01N), C01L(H01L), C01M(H01Q), C01O(H01O),
 C01P(H01P), C01Q(H01T), C01R(H01R), C01S(H01U)
;
_shelx_res_checksum              33148
_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 1.212
_oxdiff_exptl_absorpt_empirical_full_min 0.855