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_7159091
_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         'C29 H24 F3 N3'
_chemical_formula_sum            'C29 H24 F3 N3'
_chemical_formula_weight         471.51
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 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                90
_cell_angle_beta                 91.6634(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.86737(3)
_cell_length_b                   15.02535(6)
_cell_length_c                   17.36072(7)
_cell_measurement_reflns_used    42917
_cell_measurement_temperature    99.99(10)
_cell_measurement_theta_max      73.7750
_cell_measurement_theta_min      3.8830
_cell_volume                     2312.087(15)
_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      99.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.991
_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    -33.00  28.00   0.50    0.50    --    0.00 -82.00 150.00  122
  2  \w    -50.00  53.00   0.50    0.50    --   32.00 -53.00-135.68  206
  3  \w     10.00  58.00   0.50    0.50    --   36.00  71.00  67.39   96
  4  \w     64.00 107.00   0.50    0.50    --   36.00  71.00  67.39   86
  5  \w     13.00  38.00   0.50    0.50    --   40.00  71.00-102.23   50
  6  \w     82.00 108.00   0.50    0.50    --   40.00  71.00-102.23   52
  7  \w     21.00  70.00   0.50    0.50    --   48.00  72.00 131.77   98
  8  \w     83.00 135.00   0.50    0.50    --   48.00  72.00 131.77  104
  9  \w     31.00  66.00   0.50    0.50    --   56.00  74.00-102.69   70
 10  \w     29.00  63.00   0.50    0.50    --   56.00  73.00 147.54   68
 11  \w     32.00  66.00   0.50    0.50    --   60.00  74.00   3.47   68
 12  \w    109.00 146.00   0.50    0.50    --   60.00  74.00-146.98   74
 13  \w     34.00  63.00   0.50    0.50    --   60.00  75.00  29.26   58
 14  \w     32.00  71.00   0.50    0.50    --   60.00  74.00-146.98   78
 15  \w     77.00 104.00   0.50    0.50    --   60.00  74.00-146.98   54
 16  \w     32.00  75.00   0.50    0.50    --   60.00  75.00 -62.91   86
 17  \w     44.00  75.00   0.50    0.50    --   72.00  75.00 -18.23   62
 18  \w     44.00  79.00   0.50    0.50    --   72.00  75.00  39.32   70
 19  \w     45.00  79.00   0.50    0.50    --   72.00  73.00 139.89   68
 20  \w     44.00  69.00   0.50    0.50    --   72.00  75.00 -58.93   50
 21  \w     49.00  77.00   0.50    0.50    --   76.00  75.00  67.56   56
 22  \w     48.00  74.00   0.50    0.50    --   76.00  74.00  -3.55   52
 23  \w     48.00  83.00   0.50    0.50    --   76.00  74.00 152.33   70
 24  \w    142.00 169.00   0.50    0.50    --   80.00  75.00-135.17   54
 25  \w     52.00  86.00   0.50    0.50    --   80.00  75.00-135.17   68
 26  \w     57.00  96.00   0.50    0.50    --   80.00  69.00 -47.54   78
 27  \w     87.00 130.00   0.50    0.50    --   80.00  73.00  84.83   86
 28  \w     54.00  81.00   0.50    0.50    --   80.00  73.00  84.83   54
 29  \w    114.00 168.00   0.50    0.50    --   80.00  69.00 -47.54  108
 30  \w    124.00 173.00   0.50    0.50    --   84.00  73.00 109.50   98
 31  \w     57.00 118.00   0.50    0.50    --   84.00  73.00 109.50  122
 32  \w     59.00 172.00   0.50    0.50    --   84.00  68.00-176.98  226
 33  \w     52.00 122.00   0.50    0.50    --   94.60 -82.00   0.00  140
 34  \w     21.00 123.00   0.50    0.50    --   94.60 -82.00 120.00  204
 35  \w    143.00 169.00   0.50    0.50    --   94.60  45.00-180.00   52
 36  \w     75.00 134.00   0.50    0.50    --   94.60  45.00-180.00  118
 37  \w      8.00 109.00   0.50    0.50    --   94.60 -61.00 120.00  202
 38  \w     96.00 124.00   0.50    0.50    --   94.60 -77.00-120.00   56
 39  \w      5.00  92.00   0.50    0.50    --   94.60 -77.00-120.00  174
 40  \w     66.00 184.00   0.50    0.50    --   94.60  74.00  75.80  236
 41  \w     75.00 125.00   0.50    0.50    --   94.60  75.00 -61.28  100
 42  \w     72.00 146.00   0.50    0.50    --   94.60  61.00 -60.00  148
 43  \w     70.00 181.00   0.50    0.50    --   94.60  67.00  28.03  222
 44  \w     74.00 165.00   0.50    0.50    --   94.60  50.00  -2.57  182
 45  \w      6.00 106.00   0.50    0.50    --   94.60 -61.00   0.00  200
 46  \w     66.00 168.00   0.50    0.50    --   94.60  74.00-163.50  204
 47  \w     23.00 103.00   0.50    0.50    --   94.60 -82.00 -60.00  160
 48  \w     71.00 133.00   0.50    0.50    --   94.60  67.00   1.53  124
 49  \w     70.00 150.00   0.50    0.50    --   94.60  69.00-113.83  160
 50  \w     84.00 113.00   0.50    0.50    --   94.60 -82.00-150.00   58
 51  \w     68.00 136.00   0.50    0.50    --   94.60  72.00-101.77  136
 52  \w      7.00  34.00   0.50    0.50    --   94.60 -82.00-150.00   54
 53  \w     71.00 180.00   0.50    0.50    --   94.60  71.00 119.99  218
 54  \w     66.00 146.00   0.50    0.50    --   94.60  74.00  33.10  160
;
_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      0.1655818000
_diffrn_orient_matrix_UB_12      -0.0249808000
_diffrn_orient_matrix_UB_13      0.0184009000
_diffrn_orient_matrix_UB_21      -0.0161586000
_diffrn_orient_matrix_UB_22      0.0336817000
_diffrn_orient_matrix_UB_23      0.0831580000
_diffrn_orient_matrix_UB_31      -0.0500946000
_diffrn_orient_matrix_UB_32      -0.0936209000
_diffrn_orient_matrix_UB_33      0.0249955000
_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  0.0269
_diffrn_reflns_av_unetI/netI     0.0099
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            55613
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.072
_diffrn_reflns_theta_min         3.892
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.802
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.77121
_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    1.355
_exptl_crystal_description       block
_exptl_crystal_F_000             984
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.272
_refine_diff_density_min         -0.352
_refine_diff_density_rms         0.062
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     319
_refine_ls_number_reflns         4647
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.073
_refine_ls_R_factor_all          0.0381
_refine_ls_R_factor_gt           0.0377
_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^)+(0.0434P)^2^+1.1530P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0925
_refine_ls_wR_factor_ref         0.0928
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4570
_reflns_number_total             4647
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ob02241a2.cif
_cod_data_source_block           20210108_20201210dce
_cod_depositor_comments
'Adding full bibliography for 7159091--7159092.cif.'
_cod_original_cell_volume        2312.087(16)
_cod_database_code               7159091
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.856
_shelx_estimated_absorpt_t_min   0.767
_reflns_odcompleteness_completeness 100.00
_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 Aromatic/amide H refined with riding coordinates:
 C00C(H00C), C00D(H00D), C00E(H00E), C00F(H00F), C00M(H00M), C00N(H00N),
 C00O(H00O), C00P(H00P), C00R(H00R), C00S(H00S), C00U(H00U), C00V(H00V),
 C00X(H00X), C00Y(H00Y), C00Z(H00Z)
2.b Idealised Me refined as rotating group:
 C00Q(H00A,H00B,H00G), C00T(H00H,H00I,H00J), C00W(H00K,H00L,H00Q)
;
_shelx_res_checksum              46590
_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 2.061
_oxdiff_exptl_absorpt_empirical_full_min 0.576