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_7062703
_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         'C18 H15 F3 O'
_chemical_formula_sum            'C18 H15 F3 O'
_chemical_formula_weight         304.30
_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                 93.721(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.8404(12)
_cell_length_b                   5.1873(5)
_cell_length_c                   18.6784(10)
_cell_measurement_reflns_used    2115
_cell_measurement_temperature    100(4)
_cell_measurement_theta_max      69.9710
_cell_measurement_theta_min      3.6620
_cell_volume                     1434.9(2)
_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(4)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.967
_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    -97.00 -34.00   0.50    6.27    --  -38.57 -76.00  63.00  126
  2  \w    -62.00   3.00   0.50    6.27    --  -38.57  76.00-169.00  130
  3  \w     44.00 102.00   0.50    6.27    --   38.57  76.00-169.00  116
  4  \w      7.00  34.00   0.50    6.27    --   38.57 -76.00  63.00   54
  5  \w     74.00 157.00   0.50   25.08    --  100.00  76.00-169.00  166
  6  \w     36.00 127.00   0.50   25.08    --  100.00 -76.00  63.00  182
  7  \w    -62.00 -36.00   0.50    6.27    --  -38.57  65.00-180.00   52
  8  \w   -110.00 -45.00   0.50    6.27    --  -38.57 -21.00  30.00  130
  9  \w    -55.00 -29.00   0.50    6.27    --  -38.57  21.00-150.00   52
 10  \w      1.00  26.00   0.50    6.27    --  -38.57  65.00-180.00   50
 11  \w    -24.00  11.00   0.50    6.27    --  -38.57  21.00-150.00   70
 12  \w   -101.00 -59.00   0.50    6.27    --  -38.57 -65.00 -30.00   84
 13  \w    -50.00 -15.00   0.50    6.27    --  -38.57 -65.00 -30.00   70
 14  \w     26.00  62.00   0.50    6.27    --   38.57  43.00 -60.00   72
 15  \w     -3.00  35.00   0.50    6.27    --   38.57 -32.00 -90.00   76
 16  \w    -18.00  51.00   0.50    6.27    --   38.57 -43.00  60.00  138
 17  \w     64.00  89.00   0.50    6.27    --   38.57  43.00 -60.00   50
 18  \w     72.00  97.00   0.50   25.08    --  100.00 178.00 -60.00   50
 19  \w     81.00 114.00   0.50   25.08    --  100.00  22.00 120.00   66
 20  \w     47.00  73.00   0.50   25.08    --  100.00 -22.00  30.00   52
 21  \w     89.00 115.00   0.50   25.08    --  100.00  37.00 -60.00   52
 22  \w     79.00 154.00   0.50   25.08    --  100.00  61.00 150.00  150
 23  \w     92.00 125.00   0.50   25.08    --  100.00  93.00 150.00   66
 24  \w     60.00 109.00   0.50   25.08    --  100.00 -37.00-180.00   98
 25  \w     75.00 118.00   0.50   25.08    --  100.00 -61.00 -60.00   86
 26  \w     35.00  61.00   0.50   25.08    --  100.00 -61.00 -60.00   52
 27  \w     85.00 123.00   0.50   25.08    --  100.00  93.00 -60.00   76
 28  \w     49.00  74.00   0.50   25.08    --  100.00 -61.00 150.00   50
 29  \w     35.00  99.00   0.50   25.08    --  100.00 -45.00  30.00  128
 30  \w     93.00 118.00   0.50   25.08    --  100.00  37.00   0.00   50
 31  \w     78.00 116.00   0.50   25.08    --  100.00  61.00 120.00   76
 32  \w    130.00 156.00   0.50   25.08    --  100.00  61.00 120.00   52
 33  \w     94.00 156.00   0.50   25.08    --  100.00  37.00  60.00  124
 34  \w    112.00 148.00   0.50   25.08    --  100.00 178.00 -60.00   72
 35  \w    129.00 157.00   0.50   25.08    --  100.00  22.00 120.00   56
 36  \w     86.00 115.00   0.50   25.08    --  100.00 -22.00  30.00   58
 37  \w     89.00 121.00   0.50   25.08    --  100.00  37.00 -30.00   64
 38  \w     87.00 156.00   0.50   25.08    --  100.00  30.00 -90.00  138
 39  \w     -6.00  19.00   0.50    6.27    --   38.57 -76.00  63.00   50
 40  \w      2.00  27.00   0.50    6.27    --  -38.57  65.00 -60.00   50
 41  \w    -55.00 -24.00   0.50    6.27    --  -38.57  65.00 -60.00   62
 42  \w    -94.00 -69.00   0.50    6.27    --  -38.57 138.00-180.00   50
 43  \w    -55.00 -14.00   0.50    6.27    --  -38.57 138.00-180.00   82
 44  \w     69.00  95.00   0.50    6.27    --   38.57  32.00 120.00   52
 45  \w     30.00  96.00   0.50    6.27    --   38.57-138.00  90.00  132
;
_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      -0.0387449000
_diffrn_orient_matrix_UB_12      0.1488856000
_diffrn_orient_matrix_UB_13      0.0623493000
_diffrn_orient_matrix_UB_21      0.0430013000
_diffrn_orient_matrix_UB_22      -0.1969047000
_diffrn_orient_matrix_UB_23      0.0536604000
_diffrn_orient_matrix_UB_31      0.0864368000
_diffrn_orient_matrix_UB_32      0.1653383000
_diffrn_orient_matrix_UB_33      0.0076382000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0633
_diffrn_reflns_av_unetI/netI     0.0625
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.967
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            7791
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.967
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.489
_diffrn_reflns_theta_min         3.690
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.955
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.43588
_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    1.409
_exptl_crystal_description       needle
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.005
_exptl_crystal_size_min          0.005
_refine_diff_density_max         0.455
_refine_diff_density_min         -0.475
_refine_diff_density_rms         0.113
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         2710
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.081
_refine_ls_R_factor_all          0.1219
_refine_ls_R_factor_gt           0.0917
_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^)+(0.1592P)^2^+2.3176P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2474
_refine_ls_wR_factor_ref         0.2780
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1962
_reflns_number_total             2710
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3nj02990e2.cif
_cod_data_source_block           okl494
_cod_depositor_comments
'Adding full bibliography for 7062703--7062708.cif.'
_cod_original_cell_volume        1434.87(19)
_cod_database_code               7062703
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'F3 O C18'
_diffrn_oxdiff_ac3_digest_frames
;
01d96988128611500800c56c2b67b9b5f000026489a
;
_diffrn_oxdiff_ac3_digest_hkl
;
010e279b3763e9db95201c2650ee84fa305ca0
;
_reflns_odcompleteness_completeness 94.88
_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:
 C9(H9)
2.b Aromatic/amide H refined with riding coordinates:
 C16(H16), C2(H2), C8(H8), C14(H14), C13(H13), C7(H7), C5(H5), C6(H6)
2.c Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C18(H18A,H18B,H18C)
;
_shelx_res_checksum              42784
_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 4.041
_oxdiff_exptl_absorpt_empirical_full_min 0.401