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_7062707
_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         'C20 H17 F3 O3 S'
_chemical_formula_sum            'C20 H17 F3 O3 S'
_chemical_formula_weight         394.39
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2022-09-08
_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                 108.952(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.4778(2)
_cell_length_b                   7.91980(10)
_cell_length_c                   17.0401(3)
_cell_measurement_reflns_used    9043
_cell_measurement_temperature    99.9(7)
_cell_measurement_theta_max      79.3840
_cell_measurement_theta_min      3.4660
_cell_volume                     1720.29(5)
_computing_cell_refinement       'CrysAlisPro 1.171.41.118a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.118a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.118a (Rigaku OD, 2021)'
_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      99.9(7)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.970
_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     72.00 111.00   0.50    0.35    --   47.35  77.00 160.00   78
  2  \w    125.00 150.00   0.50    1.40    --  113.25  77.00 160.00   50
  3  \w    101.00 178.00   0.50    1.40    --  113.25  45.00 120.00  154
  4  \w    101.00 169.00   0.50    1.40    --  113.25  45.00  90.00  136
  5  \w    150.00 178.00   0.50    1.40    --  113.25  45.00  60.00   56
  6  \w    115.00 141.00   0.50    1.40    --  113.25  45.00  60.00   52
  7  \w     92.00 168.00   0.50    1.40    --  113.25  77.00-180.00  152
  8  \w    -70.00  25.00   0.50    0.35    --  -47.35  77.00 160.00  190
  9  \w   -102.00 -50.00   0.50    1.40    -- -106.00  77.00 160.00  104
 10  \w    -67.00 -34.00   0.50    1.40    -- -106.00  61.00 150.00   66
 11  \w   -105.00 -58.00   0.50    1.40    -- -106.00  77.00   0.00   94
 12  \w    -69.00 -43.00   0.50    1.40    -- -106.00  61.00   0.00   52
 13  \w    -60.00 -33.00   0.50    1.40    -- -106.00  61.00 -60.00   54
 14  \w    -70.00 -45.00   0.50    1.40    -- -106.00  61.00 -90.00   50
 15  \w   -103.00 -30.00   0.50    0.35    --  -47.35 -77.00  34.00  146
 16  \w   -177.00 -84.00   0.50    1.40    -- -106.00 -77.00  34.00  186
 17  \w   -111.00 -76.00   0.50    0.35    --  -47.35-125.00 150.00   70
 18  \w      6.00  40.00   0.50    0.35    --   47.35 -77.00  34.00   68
 19  \w    -24.00  26.00   0.50    0.35    --   47.35 -19.00-150.00  100
 20  \w     75.00 118.00   0.50    0.35    --   47.35 125.00-150.00   86
 21  \w     45.00  71.00   0.50    1.40    --  113.25 -61.00-180.00   52
 22  \w     42.00  67.00   0.50    1.40    --  113.25 -61.00-150.00   50
 23  \w     42.00  67.00   0.50    1.40    --  113.25 -61.00 -90.00   50
 24  \w     71.00  96.00   0.50    1.40    --  113.25 -77.00 -90.00   50
 25  \w     47.00  96.00   0.50    1.40    --  113.25 -77.00  34.00   98
 26  \w     42.00  68.00   0.50    1.40    --  113.25 -61.00  60.00   52
 27  \w     44.00  69.00   0.50    1.40    --  113.25 -61.00  30.00   50
;
_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      -0.0824792000
_diffrn_orient_matrix_UB_12      -0.0223273000
_diffrn_orient_matrix_UB_13      0.0441024000
_diffrn_orient_matrix_UB_21      -0.0561632000
_diffrn_orient_matrix_UB_22      0.1615071000
_diffrn_orient_matrix_UB_23      -0.0421920000
_diffrn_orient_matrix_UB_31      -0.0681508000
_diffrn_orient_matrix_UB_32      -0.1060249000
_diffrn_orient_matrix_UB_33      -0.0735897000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0310
_diffrn_reflns_av_unetI/netI     0.0289
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            12865
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.845
_diffrn_reflns_theta_min         3.467
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.136
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.86081
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.118a (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    1.523
_exptl_crystal_description       prism
_exptl_crystal_F_000             816
_exptl_crystal_size_max          0.09
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.399
_refine_diff_density_min         -0.307
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.102
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     246
_refine_ls_number_reflns         3629
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.102
_refine_ls_R_factor_all          0.0369
_refine_ls_R_factor_gt           0.0338
_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^)+(0.0412P)^2^+1.0315P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0920
_refine_ls_wR_factor_ref         0.0938
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3299
_reflns_number_total             3629
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3nj02990e2.cif
_cod_data_source_block           20398_okl170
_cod_depositor_comments
'Adding full bibliography for 7062703--7062708.cif.'
_cod_database_code               7062707
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C20 H7 F3 O3 S1'
_reflns_odcompleteness_completeness 99.95
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     72.42
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C3(H3), C4(H4)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B)
2.c Aromatic/amide H refined with riding coordinates:
 C8(H8), C18(H18), C11(H11), C17(H17), C14(H14), C16(H16), C15(H15)
2.d Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C), C20(H20A,H20B,H20C)
;
_shelx_res_checksum              47909
_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 1.350
_oxdiff_exptl_absorpt_empirical_full_min 0.740