TfOH-promoted multichannel transformations of trifluoromethyl side chain substituted thiophene and furan families to access antimicrobial agents
Khoroshilova, Olesya V.; Borovkova, Kristina E.; Nikiforova, Lia R.; Salmova, Julia V.; Taraskin, Artem O.; Spiridonova, Daria V.; Vasilyev, Aleksander V.; New Journal of Chemistry 47 (2023) 18492–18516; doi:10.1039/D3NJ02990E

data_7062706
_publ_section_title
;
 TfOH-promoted multichannel transformations of trifluoromethyl side chain
 substituted thiophene and furan families to access antimicrobial agents
;
_journal_issue                   39
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              18492
_journal_page_last               18516
_journal_paper_doi               10.1039/D3NJ02990E
_journal_volume                  47
_journal_year                    2023
_chemical_formula_moiety         'C19 H17 F3 O'
_chemical_formula_sum            'C19 H17 F3 O'
_chemical_formula_weight         318.32
_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             2022-12-29
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_audit_update_record
;
2022-12-29 deposited with the CCDC.	2023-09-11 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 93.4883(14)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.85016(9)
_cell_length_b                   11.07614(16)
_cell_length_c                   23.2374(3)
_cell_measurement_reflns_used    7817
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      70.2700
_cell_measurement_theta_min      3.7940
_cell_volume                     1502.93(4)
_computing_cell_refinement       'CrysAlisPro 1.171.40.50a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.50a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.50a (Rigaku OD, 2019)'
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 0.999
_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    124.00 154.00   0.50    1.04    --  100.00  89.00-156.00   60
  2  \w     39.00  65.00   0.50    1.04    --  100.00 -89.00  88.00   52
  3  \w     80.00 123.00   0.50    1.04    --  100.00 -89.00  88.00   86
  4  \w     79.00 110.00   0.50    1.04    --  100.00  89.00-156.00   62
  5  \w    -43.00   6.00   0.50    0.26    --  -38.82  89.00-156.00   98
  6  \w    -60.00  -2.00   0.50    0.26    --  -38.82 -11.00  60.00  116
  7  \w    -56.00   8.00   0.50    0.26    --  -38.82  43.00-180.00  128
  8  \w    -86.00 -23.00   0.50    0.26    --  -38.82 -43.00 -30.00  126
  9  \w   -111.00 -74.00   0.50    0.26    --  -38.82 -11.00  60.00   74
 10  \w    -26.00   0.00   0.50    0.26    --   38.82 -89.00  88.00   52
 11  \w     28.00  53.00   0.50    0.26    --   38.82  32.00 -90.00   50
 12  \w     -4.00  43.00   0.50    0.26    --   38.82 -32.00   0.00   94
 13  \w     33.00  58.00   0.50    0.26    --   38.82 -89.00  88.00   50
 14  \w     48.00  89.00   0.50    0.26    --   38.82-138.00-120.00   82
 15  \w    -26.00  46.00   0.50    0.26    --   38.82 -43.00 120.00  144
 16  \w    -26.00  52.00   0.50    0.26    --   38.82 -43.00-150.00  156
 17  \w     31.00  56.00   0.50    1.04    --  100.00-111.00 150.00   50
 18  \w     33.00 117.00   0.50    1.04    --  100.00 -22.00  30.00  168
 19  \w     75.00 116.00   0.50    1.04    --  100.00 -45.00  60.00   82
 20  \w     81.00 107.00   0.50    1.04    --  100.00 -69.00-150.00   52
 21  \w     99.00 125.00   0.50    1.04    --  100.00 -69.00  90.00   52
 22  \w     44.00  70.00   0.50    1.04    --  100.00 -69.00-150.00   52
 23  \w     35.00  60.00   0.50    1.04    --  100.00 -45.00  60.00   50
 24  \w     34.00  59.00   0.50    1.04    --  100.00 -69.00  90.00   50
 25  \w     92.00 118.00   0.50    1.04    --  100.00 -45.00 -90.00   52
 26  \w    126.00 152.00   0.50    1.04    --  100.00  69.00-120.00   52
 27  \w    122.00 148.00   0.50    1.04    --  100.00  37.00 -60.00   52
 28  \w     34.00 101.00   0.50    1.04    --  100.00 -93.00 -90.00  134
 29  \w     35.00  84.00   0.50    1.04    --  100.00 -45.00 -90.00   98
 30  \w     77.00 130.00   0.50    1.04    --  100.00  77.00 -90.00  106
 31  \w    117.00 157.00   0.50    1.04    --  100.00  30.00-120.00   80
 32  \w    112.00 149.00   0.50    1.04    --  100.00  22.00 150.00   74
 33  \w     80.00 105.00   0.50    1.04    --  100.00 -93.00  60.00   50
 34  \w     83.00 110.00   0.50    1.04    --  100.00-111.00 150.00   54
 35  \w     78.00 123.00   0.50    1.04    --  100.00  69.00-120.00   90
 36  \w     81.00 106.00   0.50    1.04    --  100.00-111.00  30.00   50
 37  \w     48.00  74.00   0.50    1.04    --  100.00-111.00  30.00   52
 38  \w     82.00 108.00   0.50    1.04    --  100.00  53.00-150.00   52
 39  \w     81.00 120.00   0.50    1.04    --  100.00 -53.00  90.00   78
 40  \w    100.00 142.00   0.50    1.04    --  100.00  30.00   0.00   84
 41  \w     86.00 112.00   0.50    1.04    --  100.00  37.00 -60.00   52
 42  \w     -2.00  24.00   0.50    0.26    --   38.82 -89.00  88.00   52
 43  \w     75.00 106.00   0.50    0.26    --   38.82  32.00  30.00   62
 44  \w     15.00  45.00   0.50    0.26    --   38.82  77.00  90.00   60
 45  \w     21.00  46.00   0.50    0.26    --   38.82  21.00-180.00   50
 46  \w     31.00  57.00   0.50    0.26    --   38.82  32.00  30.00   52
 47  \w     79.00 105.00   0.50    0.26    --   38.82  77.00  90.00   52
 48  \w     21.00  53.00   0.50    0.26    --   38.82  21.00-120.00   64
 49  \w     82.00 108.00   0.50    0.26    --   38.82  32.00-120.00   52
 50  \w     79.00 105.00   0.50    0.26    --   38.82  21.00-180.00   52
 51  \w     -2.00  24.00   0.50    0.26    --   38.82-104.00   0.00   52
 52  \w     49.00  74.00   0.50    0.26    --   38.82-104.00   0.00   50
 53  \w     28.00  72.00   0.50    1.04    --  100.00 -15.00 -30.00   88
 54  \w     69.00 126.00   0.50    1.04    --  100.00 -77.00 120.00  114
 55  \w    106.00 150.00   0.50    1.04    --  100.00  69.00  90.00   88
 56  \w     88.00 114.00   0.50    1.04    --  100.00  30.00   0.00   52
 57  \w     33.00  65.00   0.50    1.04    --  100.00 -86.00 -60.00   64
 58  \w     60.00 101.00   0.50    1.04    --  100.00 -22.00  90.00   82
 59  \w     79.00 130.00   0.50    1.04    --  100.00 -86.00  30.00  102
 60  \w     34.00  60.00   0.50    1.04    --  100.00  -7.00  90.00   52
 61  \w    108.00 134.00   0.50    1.04    --  100.00  45.00  90.00   52
 62  \w    101.00 151.00   0.50    1.04    --  100.00  -7.00   0.00  100
 63  \w     83.00 111.00   0.50    1.04    --  100.00-111.00 -30.00   56
 64  \w     90.00 119.00   0.50    1.04    --  100.00  -7.00  90.00   58
 65  \w    114.00 154.00   0.50    1.04    --  100.00  37.00-180.00   80
 66  \w     81.00 121.00   0.50    1.04    --  100.00 -86.00 -60.00   80
 67  \w     54.00  80.00   0.50    1.04    --  100.00-111.00-150.00   52
 68  \w     86.00 111.00   0.50    1.04    --  100.00-111.00-150.00   50
 69  \w     48.00  74.00   0.50    1.04    --  100.00 -93.00 120.00   52
 70  \w     67.00 115.00   0.50    1.04    --  100.00 -37.00  90.00   96
 71  \w     90.00 115.00   0.50    1.04    --  100.00  61.00-150.00   50
 72  \w     97.00 123.00   0.50    1.04    --  100.00  37.00 -90.00   52
 73  \w     85.00 111.00   0.50    1.04    --  100.00  61.00 -60.00   52
 74  \w     86.00 112.00   0.50    1.04    --  100.00  45.00 150.00   52
 75  \w    115.00 147.00   0.50    1.04    --  100.00  45.00-150.00   64
 76  \w     80.00 140.00   0.50    1.04    --  100.00  53.00 120.00  120
 77  \w     83.00 109.00   0.50    1.04    --  100.00  45.00-150.00   52
 78  \w    132.00 157.00   0.50    1.04    --  100.00  37.00 -90.00   50
 79  \w     79.00 111.00   0.50    1.04    --  100.00-111.00-120.00   64
 80  \w     87.00 113.00   0.50    1.04    --  100.00 -45.00  30.00   52
 81  \w     83.00 109.00   0.50    1.04    --  100.00  53.00 -30.00   52
 82  \w     81.00 149.00   0.50    1.04    --  100.00  93.00  60.00  136
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'SuperNova, Single source at offset/far, HyPix3000'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0537650000
_diffrn_orient_matrix_UB_12      0.1041022000
_diffrn_orient_matrix_UB_13      0.0410502000
_diffrn_orient_matrix_UB_21      0.1118033000
_diffrn_orient_matrix_UB_22      -0.0714589000
_diffrn_orient_matrix_UB_23      0.0511366000
_diffrn_orient_matrix_UB_31      0.2329009000
_diffrn_orient_matrix_UB_32      0.0583155000
_diffrn_orient_matrix_UB_33      -0.0104866000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0476
_diffrn_reflns_av_unetI/netI     0.0314
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            15404
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.444
_diffrn_reflns_theta_min         3.812
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.936
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.68976
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.50a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.407
_exptl_crystal_description       plate
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.205
_refine_diff_density_min         -0.283
_refine_diff_density_rms         0.048
_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     211
_refine_ls_number_reflns         2871
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.073
_refine_ls_R_factor_all          0.0513
_refine_ls_R_factor_gt           0.0451
_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/[\s^2^(Fo^2^)+(0.0575P)^2^+0.5936P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1112
_refine_ls_wR_factor_ref         0.1155
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2523
_reflns_number_total             2871
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3nj02990e2.cif
_cod_data_source_block           okl482
_cod_depositor_comments
'Adding full bibliography for 7062703--7062708.cif.'
_cod_database_code               7062706
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C20 F3'
_diffrn_oxdiff_ac3_digest_frames
;
01a5aa23b16dff8b5ce1739810b93ee9ba000310150
;
_diffrn_oxdiff_ac3_digest_hkl
;
01351fe7e4d2bef2b71747a28a25224ea4235a
;
_reflns_odcompleteness_completeness 96.23
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     72.42
_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:
 C005(H005), C009(H009), C00D(H00D)
2.b Aromatic/amide H refined with riding coordinates:
 C00B(H00B), C00C(H00C), C00E(H00E), C00F(H00F), C00I(H00I)
2.c Idealised Me refined as rotating group:
 C00H(H00A,H00G,H00H), C00K(H00J,H00K,H00L), C00N(H00M,H00N,H00O)
;
_shelx_res_checksum              35932
_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 1.366
_oxdiff_exptl_absorpt_empirical_full_min 0.637