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_7062705
_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_absolute_configuration ad
_chemical_formula_moiety         'C20 H17 F3 O2 S'
_chemical_formula_sum            'C20 H17 F3 O2 S'
_chemical_formula_weight         378.39
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2018-12-18
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2023-03-13 deposited with the CCDC.	2023-09-11 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 100.307(6)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.3648(5)
_cell_length_b                   5.3613(3)
_cell_length_c                   17.6629(10)
_cell_measurement_reflns_used    2609
_cell_measurement_temperature    104.7(9)
_cell_measurement_theta_max      71.6610
_cell_measurement_theta_min      4.7750
_cell_volume                     872.50(9)
_computing_cell_refinement       'CrysAlisPro 1.171.39.35a (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.35a (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.35a (Rigaku OD, 2017)'
_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
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      104.7(9)
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            HyPix3000
_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   -101.00 -40.00   0.50    1.81    --  -41.22 -56.00-136.00  122
  2  \w    -30.00  22.00   0.50    1.81    --  -41.22  56.00   5.00  104
  3  \w     69.00  94.00   0.50    1.81    --   41.22  56.00   5.00   50
  4  \w     28.00  54.00   0.50    1.81    --   41.22  56.00   5.00   52
  5  \w     38.00 118.00   0.50    8.00    --  101.00 -56.00-136.00  160
  6  \w     89.00 154.00   0.50    8.00    --  101.00  56.00   5.00  130
  7  \w    -94.00 -66.00   0.50    1.81    --  -41.22 -54.00  30.00   56
  8  \w    -56.00 -28.00   0.50    1.81    --  -41.22 -54.00  30.00   56
  9  \w    -13.00  22.00   0.50    1.81    --  -41.22  32.00 -30.00   70
 10  \w     12.00  55.00   0.50    1.81    --   41.22 -56.00-136.00   86
 11  \w    -19.00   8.00   0.50    1.81    --   41.22 -56.00-136.00   54
 12  \w     18.00  45.00   0.50    1.81    --   41.22 -32.00  60.00   54
 13  \w     37.00  67.00   0.50    1.81    --   41.22 -89.00-150.00   60
 14  \w    -23.00  49.00   0.50    1.81    --   41.22 -32.00  90.00  144
 15  \w     -8.00  17.00   0.50    1.81    --   41.22 -89.00-150.00   50
 16  \w    -20.00   5.00   0.50    1.81    --   41.22 -32.00  60.00   50
 17  \w     77.00 122.00   0.50    8.00    --  101.00-133.00 120.00   90
 18  \w     58.00 114.00   0.50    8.00    --  101.00-111.00 150.00  112
 19  \w     39.00  79.00   0.50    8.00    --  101.00 -42.00 -90.00   80
 20  \w     40.00  65.00   0.50    8.00    --  101.00-133.00 120.00   50
 21  \w     42.00  82.00   0.50    8.00    --  101.00 -17.00  90.00   80
 22  \w     97.00 152.00   0.50    8.00    --  101.00  77.00  30.00  110
 23  \w     48.00  90.00   0.50    8.00    --  101.00 178.00-180.00   84
 24  \w     69.00 101.00   0.50    8.00    --  101.00 -33.00-180.00   64
 25  \w     37.00  63.00   0.50    8.00    --  101.00 -33.00-180.00   52
 26  \w     92.00 150.00   0.50    8.00    --  101.00  25.00 -30.00  116
 27  \w     38.00 103.00   0.50    8.00    --  101.00 -42.00  30.00  130
 28  \w     76.00 110.00   0.50    8.00    --  101.00-111.00-120.00   68
 29  \w     35.00  73.00   0.50    8.00    --  101.00-111.00-120.00   76
 30  \w    111.00 152.00   0.50    8.00    --  101.00 111.00 -60.00   82
 31  \w    103.00 128.00   0.50    8.00    --  101.00  33.00-120.00   50
 32  \w     95.00 137.00   0.50    8.00    --  101.00  33.00   0.00   84
 33  \w    104.00 131.00   0.50    8.00    --  101.00 178.00-180.00   54
 34  \w     20.00  47.00   0.50    1.81    --   41.22  77.00-150.00   54
 35  \w     -2.00  23.00   0.50    1.81    --  -41.22  65.00  30.00   50
 36  \w    -60.00 -28.00   0.50    1.81    --  -41.22 -43.00  90.00   64
 37  \w    -57.00 -30.00   0.50    1.81    --  -41.22  65.00  30.00   54
 38  \w     35.00  75.00   0.50    1.81    --   41.22  32.00 120.00   80
 39  \w     30.00  57.00   0.50    1.81    --   41.22  65.00 150.00   54
 40  \w     28.00  67.00   0.50    1.81    --   41.22  65.00 120.00   78
 41  \w     51.00  90.00   0.50    1.81    --   41.22  32.00-180.00   78
 42  \w     76.00 103.00   0.50    8.00    --  101.00  76.00  83.37   54
 43  \w     35.00  87.00   0.50    8.00    --  101.00 -87.00-120.00  104
 44  \w     81.00 110.00   0.50    8.00    --  101.00  63.00 110.74   58
 45  \w    123.00 152.00   0.50    8.00    --  101.00  93.00-180.00   58
 46  \w     86.00 117.00   0.50    8.00    --  101.00  59.00  60.00   62
 47  \w     90.00 115.00   0.50    8.00    --  101.00  42.00  60.00   50
 48  \w     31.00 107.50   0.50    8.00    --  101.00 -17.00-120.00  153
;
_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      0.0102572000
_diffrn_orient_matrix_UB_12      -0.0798365000
_diffrn_orient_matrix_UB_13      -0.0826761000
_diffrn_orient_matrix_UB_21      -0.1261236000
_diffrn_orient_matrix_UB_22      0.1765173000
_diffrn_orient_matrix_UB_23      -0.0316461000
_diffrn_orient_matrix_UB_31      0.1092475000
_diffrn_orient_matrix_UB_32      0.2123356000
_diffrn_orient_matrix_UB_33      -0.0045005000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0575
_diffrn_reflns_av_unetI/netI     0.0716
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            5999
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         67.957
_diffrn_reflns_theta_min         2.543
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.036
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.43798
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.35a (Rigaku Oxford Diffraction, 2017)
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    1.440
_exptl_crystal_description       plate
_exptl_crystal_F_000             392
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_refine_diff_density_max         1.040
_refine_diff_density_min         -0.488
_refine_diff_density_rms         0.082
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.37(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     232
_refine_ls_number_reflns         2820
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0774
_refine_ls_R_factor_gt           0.0693
_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^)+(0.0964P)^2^+1.0481P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1825
_refine_ls_wR_factor_ref         0.1887
_reflns_Friedel_coverage         0.790
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.998
_reflns_number_gt                2489
_reflns_number_total             2820
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3nj02990e2.cif
_cod_data_source_block           okl192
_cod_depositor_comments
'Adding full bibliography for 7062703--7062708.cif.'
_cod_database_code               7062705
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C20 O2 F3 S'
_reflns_odcompleteness_completeness 99.79
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     71.55
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.63(6)
 0.37(6)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3. Uiso/Uaniso restraints and constraints
Uanis(C1) = Uanis(C3)
4.a Ternary CH refined with riding coordinates:
 C17(H17)
4.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C4(H4), C7(H7), C11(H11), C19(H19), C22(H22), C24(H24),
 C26(H26), C28(H28)
4.c Idealised Me refined as rotating group:
 C29(H29A,H29B,H29C), C34(H34A,H34B,H34C)
;
_shelx_res_checksum              88781
_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 1.665
_oxdiff_exptl_absorpt_empirical_full_min 0.165