Synthesis of 1-(β-coumarinyl)-1-(β-indolyl)trifluoroethanols through regioselective Friedel‒Crafts alkylation of indoles with β-(trifluoroacetyl)coumarins catalyzed by Sc(OTf)3
Shi, Lijun; Liu, Ying; Wang, Caixia; Yuan, Xinxin; Liu, Xiaobiao; Wu, Lulu; Pan, Zhenliang; Yu, Qicheng; Xu, Cuilian; Yang, Guoyu; RSC Advances 10 (2020) 13929–13935; doi:10.1039/D0RA01237H

data_7240325
_publ_section_title
;
 Synthesis of 1-(\b-coumarinyl)-1-(\b-indolyl)trifluoroethanols through
 regioselective Friedel--Crafts alkylation of indoles with
 \b-(trifluoroacetyl)coumarins catalyzed by Sc(OTf)3
;
_journal_issue                   24
_journal_name_full               'RSC Advances'
_journal_page_first              13929
_journal_page_last               13935
_journal_paper_doi               10.1039/D0RA01237H
_journal_volume                  10
_journal_year                    2020
_chemical_formula_moiety         'C27 H20 F3 N O5'
_chemical_formula_sum            'C34 H26 F3 N O5'
_chemical_formula_weight         585.56
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2018-01-26
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2019-08-30 deposited with the CCDC.	2020-03-22 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 111.054(5)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   22.1710(10)
_cell_length_b                   8.6836(3)
_cell_length_c                   32.4701(14)
_cell_measurement_reflns_used    3765
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      69.5050
_cell_measurement_theta_min      4.1900
_cell_volume                     5834.0(5)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2312
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
  1 omega  -41.00  -12.00   0.5000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000   57.0000  -30.0000 58

  2 omega   61.00  106.00   0.5000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   77.0000  -90.0000 90

  3 omega   31.00   77.00   0.5000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -99.0000   90.0000 92

  4 omega    5.00   50.00   0.5000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -42.0000 -168.0000 90

  5 omega   35.00   61.00   0.5000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   77.0000  -30.0000 52

  6 omega  -31.00   59.00   0.5000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -37.0000    0.0000 180

  7 omega  -26.00    6.00   0.5000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -77.0000   90.0000 64

  8 omega   10.00   36.00   0.5000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -77.0000   90.0000 52

  9 omega   19.00   45.00   0.5000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   57.0000  150.0000 52

 10 omega    8.00   65.00   0.5000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   77.0000 -120.0000 114

 11 omega   77.00  102.00   0.5000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   77.0000  -30.0000 50

 12 omega   57.00   83.00   0.5000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   57.0000  150.0000 52

 13 omega   19.00   71.00   0.5000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   57.0000   30.0000 104

 14 omega   61.00  109.00   0.5000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000 -120.0000 96

 15 omega   14.00   53.00   0.5000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   77.0000  -90.0000 78

 16 omega  138.00  165.00   0.5000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000 -180.0000 54

 17 omega   40.00   90.00   0.5000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  -90.0000 100

 18 omega   39.00  112.00   0.5000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000 -150.0000 146

 19 omega   58.00   98.00   0.5000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  150.0000 80

 20 omega   38.00   91.00   0.5000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000  -90.0000 106

 21 omega   61.00   87.00   0.5000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  120.0000 52

 22 omega  101.00  128.00   0.5000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000    0.0000 54

 23 omega   98.00  176.00   0.5000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000   90.0000 156

 24 omega   38.00  105.00   0.5000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000   90.0000 134

 25 omega  102.00  162.00   0.5000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000 -120.0000 120

 26 omega   53.00   79.00   0.5000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  -30.0000 52

 27 omega  104.00  169.00   0.5000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000  -90.0000 130
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0110716000
_diffrn_orient_matrix_UB_12      -0.1754274000
_diffrn_orient_matrix_UB_13      -0.0014080000
_diffrn_orient_matrix_UB_21      -0.0721539000
_diffrn_orient_matrix_UB_22      0.0248732000
_diffrn_orient_matrix_UB_23      -0.0272608000
_diffrn_orient_matrix_UB_31      0.0145597000
_diffrn_orient_matrix_UB_32      -0.0101716000
_diffrn_orient_matrix_UB_33      -0.0428790000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0221
_diffrn_reflns_av_unetI/netI     0.0222
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_number            13560
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.064
_diffrn_reflns_theta_max         67.064
_diffrn_reflns_theta_min         4.221
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.859
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.74890
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.333
_exptl_crystal_F_000             2432
_refine_diff_density_max         3.966
_refine_diff_density_min         -0.538
_refine_diff_density_rms         0.262
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   2.354
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     327
_refine_ls_number_reflns         5221
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      2.354
_refine_ls_R_factor_all          0.2465
_refine_ls_R_factor_gt           0.2308
_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^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.5210
_refine_ls_wR_factor_ref         0.5449
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3872
_reflns_number_total             5221
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0ra01237h2.cif
_cod_data_source_block           20180138
_cod_depositor_comments
'Adding full bibliography for 7240324--7240325.cif.'
_cod_original_cell_volume        5833.9(5)
_cod_database_code               7240325
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         C40H30O5F2
_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, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C20(H20A,H20B)
2.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C7(H7), C9(H9), C10(H10), C12(H12), C16(H16), C17(H17), C18(H18),
 C22(H22), C23(H23), C24(H24), C25(H25), C26(H26), N1(H1A)
2.c Idealised Me refined as rotating group:
 C27(H27A,H27B,H27C)
2.d Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_olex2_submission_special_instructions 'No special instructions were received'