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_7062704
_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         'C12 H7 F3 O S'
_chemical_formula_sum            'C12 H7 F3 O S'
_chemical_formula_weight         256.24
_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                 97.737(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   4.7366(2)
_cell_length_b                   25.8695(8)
_cell_length_c                   8.5888(4)
_cell_measurement_reflns_used    2072
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      75.4570
_cell_measurement_theta_min      3.3880
_cell_volume                     1042.83(7)
_computing_cell_refinement       'CrysAlisPro 1.171.41.95a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.95a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.95a (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      100(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3829
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.977
_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    -70.00  31.00   1.00    2.27    --  -41.44  57.00  60.00  101
  2  \w     74.00 129.00   1.00    2.27    --   41.44 178.00  30.00   55
  3  \w     20.00  46.00   1.00    2.27    --   41.44  38.00 -60.00   26
  4  \w     67.00 110.00   1.00    2.27    --   41.44 178.00-120.00   43
  5  \w    134.00 175.00   1.00   15.00    --  112.00  77.00   0.00   41
  6  \w     66.00 100.00   1.00   15.00    --  112.00 -95.00 150.00   34
  7  \w     52.00  79.00   1.00   15.00    --  112.00 -95.00 -30.00   27
  8  \w     87.00 173.00   1.00   15.00    --  112.00  45.00-180.00   86
  9  \w    103.00 168.00   1.00   15.00    --  112.00  77.00  90.00   65
 10  \w     41.00 111.00   1.00   15.00    --  112.00-125.00 120.00   70
 11  \w    103.00 171.00   1.00   15.00    --  112.00  77.00 120.00   68
 12  \w     77.00 104.00   1.00   15.00    --  112.00-125.00 -60.00   27
 13  \w     85.00 110.00   1.00   15.00    --  112.00  30.00  90.00   25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1582405000
_diffrn_orient_matrix_UB_12      0.0483530000
_diffrn_orient_matrix_UB_13      -0.0470247000
_diffrn_orient_matrix_UB_21      -0.0024173000
_diffrn_orient_matrix_UB_22      -0.0220352000
_diffrn_orient_matrix_UB_23      -0.1668600000
_diffrn_orient_matrix_UB_31      -0.2875274000
_diffrn_orient_matrix_UB_32      0.0268667000
_diffrn_orient_matrix_UB_33      -0.0521947000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0331
_diffrn_reflns_av_unetI/netI     0.0468
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            4144
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.223
_diffrn_reflns_theta_min         3.417
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    3.012
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.76132
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.95a (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    1.632
_exptl_crystal_description       plate
_exptl_crystal_F_000             520
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.655
_refine_diff_density_min         -0.262
_refine_diff_density_rms         0.072
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         2115
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0495
_refine_ls_R_factor_gt           0.0402
_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^)+(0.0569P)^2^+0.0419P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0944
_refine_ls_wR_factor_ref         0.0999
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1812
_reflns_number_total             2115
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3nj02990e2.cif
_cod_data_source_block           22978_okl-171
_cod_depositor_comments
'Adding full bibliography for 7062703--7062708.cif.'
_cod_database_code               7062704
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C12 H7 F3 O S'
_reflns_odcompleteness_completeness 99.20
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     72.42
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Ternary CH refined with riding coordinates:
 C4(H4), C5(H5)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C7(H7), C10(H10), C9(H9), C8(H8)
;
_shelx_res_checksum              7731
_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 1.855
_oxdiff_exptl_absorpt_empirical_full_min 0.564