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_7062708
_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 H13 F3 S'
_chemical_formula_sum            'C19 H13 F3 S'
_chemical_formula_weight         330.35
_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     dual
_audit_creation_date             2023-03-15
_audit_creation_method
;
Olex2 1.5
(compiled 2023.02.24 svn.rf166f9f3 for OlexSys, GUI svn.r6725)
;
_audit_update_record
;
2023-03-15 deposited with the CCDC.	2023-09-11 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 101.3840(10)
_cell_angle_gamma                90
_cell_formula_units_Z            32
_cell_length_a                   44.8162(4)
_cell_length_b                   9.25160(10)
_cell_length_c                   29.8662(2)
_cell_measurement_reflns_used    47275
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      76.6480
_cell_measurement_theta_min      2.9970
_cell_volume                     12139.55(19)
_computing_cell_refinement       'CrysAlisPro 1.171.41.115a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.115a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.115a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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   -115.00 -33.00   0.50    2.70    --  -47.44 -64.00  54.00  164
  2  \w     52.00 116.00   0.50    2.70    --   47.44  64.00-169.00  128
  3  \w    -21.00  54.00   0.50    2.70    --   47.44 -64.00  54.00  150
  4  \w    -76.00 -51.00   0.50    9.00    -- -106.00  64.00-169.00   50
  5  \w   -171.00 -94.00   0.50    9.00    -- -106.00 -64.00  54.00  154
  6  \w    130.00 178.00   0.50    9.00    --  106.50  64.00-169.00   96
  7  \w     89.00 114.00   0.50    9.00    --  106.50  64.00-169.00   50
  8  \w     42.00  73.00   0.50    9.00    --  106.50 -64.00  54.00   62
  9  \w    -63.00  23.00   0.50    2.70    --  -47.44  64.00-169.00  172
 10  \w   -119.00 -74.00   0.50    2.70    --  -47.44-125.00-150.00   90
 11  \w     -8.00  28.00   0.50    2.70    --  -47.44  19.00 120.00   72
 12  \w    -94.00 -20.00   0.50    2.70    --  -47.44 125.00-180.00  148
 13  \w     50.00  95.00   0.50    2.70    --   47.44-125.00 -30.00   90
 14  \w   -122.00 -73.00   0.50    9.00    -- -106.00-125.00   0.00   98
 15  \w    -63.00 -33.00   0.50    9.00    -- -106.00  61.00 -90.00   60
 16  \w   -174.00-129.00   0.50    9.00    -- -106.00-125.00   0.00   90
 17  \w   -170.00-138.00   0.50    9.00    -- -106.00-125.00-150.00   64
 18  \w   -163.00 -89.00   0.50    9.00    -- -106.00 -61.00 120.00  148
 19  \w   -103.00 -77.00   0.50    9.00    -- -106.00-125.00-150.00   52
 20  \w    -70.00 -33.00   0.50    9.00    -- -106.00  61.00  30.00   74
 21  \w   -127.00 -67.00   0.50    9.00    -- -106.00 146.00-144.35  120
 22  \w   -108.00 -61.00   0.50    9.00    -- -106.00 112.00  18.38   94
 23  \w   -117.00 -69.00   0.50    9.00    -- -106.00 133.00  46.08   96
 24  \w   -177.00-104.00   0.50    9.00    -- -106.00 -94.00 150.00  146
 25  \w    -81.00 -36.00   0.50    9.00    -- -106.00 125.00 -30.00   90
 26  \w    -70.00 -39.00   0.50    9.00    -- -106.00  61.00 -30.00   62
 27  \w   -127.00 -73.00   0.50    9.00    -- -106.00 146.00 135.35  108
 28  \w   -112.00 -46.00   0.50    9.00    -- -106.00 125.00  30.00  132
 29  \w     85.00 111.00   0.50    9.00    --  106.50-125.00-150.00   52
 30  \w     39.00  80.00   0.50    9.00    --  106.50-125.00-150.00   82
 31  \w     85.00 170.00   0.50    9.00    --  106.50 125.00 -90.00  170
 32  \w     40.00  70.00   0.50    9.00    --  106.50 -61.00 -60.00   60
 33  \w     91.00 176.00   0.50    9.00    --  106.50  61.00-150.00  170
 34  \w     94.00 172.00   0.50    9.00    --  106.50  30.00 -30.00  156
 35  \w     37.00 109.00   0.50    9.00    --  106.50-120.00  28.41  144
 36  \w     86.00 111.00   0.50    9.00    --  106.50-125.00 -60.00   50
 37  \w     80.00 105.00   0.50    9.00    --  106.50 -94.00  90.00   50
 38  \w     38.00  63.00   0.50    9.00    --  106.50 -61.00  90.00   50
 39  \w     48.00  74.00   0.50    9.00    --  106.50 -94.00-120.00   52
 40  \w     58.00  90.00   0.50    9.00    --  106.50-125.00 -90.00   64
 41  \w     86.00 111.00   0.50    9.00    --  106.50-125.00  60.00   50
 42  \w     46.00  73.00   0.50    9.00    --  106.50-125.00  60.00   54
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'XtaLAB Synergy, Single source at home/near, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0343188000
_diffrn_orient_matrix_UB_12      -0.0034124000
_diffrn_orient_matrix_UB_13      -0.0207205000
_diffrn_orient_matrix_UB_21      -0.0054917000
_diffrn_orient_matrix_UB_22      0.1198969000
_diffrn_orient_matrix_UB_23      0.0332750000
_diffrn_orient_matrix_UB_31      0.0046429000
_diffrn_orient_matrix_UB_32      0.1154883000
_diffrn_orient_matrix_UB_33      -0.0351192000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0324
_diffrn_reflns_av_unetI/netI     0.0177
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       54
_diffrn_reflns_limit_h_min       -54
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_number            77853
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         69.993
_diffrn_reflns_theta_min         3.019
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.156
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.67962
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.115a (Rigaku Oxford Diffraction, 2021)
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    1.446
_exptl_crystal_description       prism
_exptl_crystal_F_000             5440
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.283
_refine_diff_density_min         -0.235
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     833
_refine_ls_number_reflns         11500
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0344
_refine_ls_R_factor_gt           0.0325
_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^)+(0.0595P)^2^+6.3651P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0963
_refine_ls_wR_factor_ref         0.0980
_reflns_Friedel_coverage         0.000
_reflns_number_gt                10689
_reflns_number_total             11500
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3nj02990e2.cif
_cod_data_source_block           19319_okl910
_cod_depositor_comments
'Adding full bibliography for 7062703--7062708.cif.'
_cod_original_cell_volume        12139.54(19)
_cod_database_code               7062708
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C19 H13 F3 S1'
_shelx_estimated_absorpt_t_max   0.882
_shelx_estimated_absorpt_t_min   0.424
_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:
 C6(H6), C6A(H6A), C6B(H6B), C6C(H6C)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C8(H8), C9(H9), C10(H10), C11(H11), C13(H13), C14(H14), C16(H16),
 C17(H17), C2A(H2A), C8A(H8A), C9A(H9A), C10A(H10A), C11A(H11A), C13A(H13A),
 C14A(H14A), C16A(H16A), C17A(H17A), C2B(H2B), C8B(H8B), C9B(H9B), C10B(H10B),
 C11B(H11B), C13B(H13B), C14B(H14B), C16B(H16B), C17B(H17B), C2C(H2C), C8C(H8C),
  C9C(H9C), C10C(H10C), C11C(H11C), C13C(H13C), C14C(H14C), C16C(H16C),
 C17C(H17C)
2.c Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C18A(H18D,H18E,H18F), C18B(H18G,H18H,H18I), C18C(H18J,
 H18K,H18L)
;
_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 2.301
_oxdiff_exptl_absorpt_empirical_full_min 0.529