Microwave-assisted palladium catalysed C-H acylation with aldehydes: synthesis and diversification of 3-acylthiophenes.
Santiago, Carlos; Jiménez-Aberasturi, Xabier; Leicea, Eztizen; Lete, Marta G.; Sotomayor, Nuria; Lete, Esther; Organic & biomolecular chemistry 20 (2022) 852–861; doi:10.1039/d1ob02176a

data_7158456
_publ_section_title
;
 Microwave-assisted palladium catalysed C-H acylation with aldehydes:
 synthesis and diversification of 3-acylthiophenes.
;
_journal_issue                   4
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              852
_journal_page_last               861
_journal_paper_doi               10.1039/d1ob02176a
_journal_volume                  20
_journal_year                    2022
_chemical_formula_moiety         'C23 H20 N S, C F3 O3 S, C H3 O0.5'
_chemical_formula_sum            'C25 H23 F3 N O3.5 S2'
_chemical_formula_weight         514.56
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2021-09-02T11:13:22-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_update_record
;
2021-09-03 deposited with the CCDC.	2021-12-15 downloaded from the CCDC.
;
_cell_angle_alpha                109.356(9)
_cell_angle_beta                 100.318(9)
_cell_angle_gamma                106.611(9)
_cell_formula_units_Z            2
_cell_length_a                   9.1139(10)
_cell_length_b                   11.7059(12)
_cell_length_c                   12.6851(14)
_cell_measurement_reflns_used    1117
_cell_measurement_temperature    150.01(10)
_cell_measurement_theta_max      22.896
_cell_measurement_theta_min      1.778
_cell_volume                     1166.1(3)
_computing_cell_refinement       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.67a (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_temperature      150.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2439
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 0.949
_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    -89.00 -63.00   1.00    9.00    --  -23.50-155.00-133.00   26
  2  \w    -93.00 -67.00   1.00    9.00    --  -23.50 -57.00 -90.00   26
  3  \w    -54.00  38.00   1.00    9.00    --   24.74 -77.00  60.00   92
  4  \w     42.00 116.00   1.00    9.00    --   24.74-178.00-120.00   74
  5  \w    -55.00  66.00   1.00    9.00    --   24.74 -77.00 -60.00  121
  6  \w    -55.00  66.00   1.00    9.00    --   24.74 -77.00-180.00  121
;
_diffrn_measurement_device       'four-circle\k-geometry diffractometer'
_diffrn_measurement_device_type  'Agilent SuperNova'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0774428
_diffrn_orient_matrix_UB_12      0.0025471
_diffrn_orient_matrix_UB_13      0.0254227
_diffrn_orient_matrix_UB_21      -0.0109703
_diffrn_orient_matrix_UB_22      0.0211172
_diffrn_orient_matrix_UB_23      0.0562561
_diffrn_orient_matrix_UB_31      -0.0338311
_diffrn_orient_matrix_UB_32      -0.065836
_diffrn_orient_matrix_UB_33      -0.0074961
_diffrn_radiation_monochromator  'Multilayer optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0547
_diffrn_reflns_av_unetI/netI     0.2095
_diffrn_reflns_Laue_measured_fraction_full 1
_diffrn_reflns_Laue_measured_fraction_max 0.949
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            7751
_diffrn_reflns_point_group_measured_fraction_full 1
_diffrn_reflns_point_group_measured_fraction_max 0.949
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.498
_diffrn_reflns_theta_min         1.785
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_current           0.8
_diffrn_source_power             0.04
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    0.284
_exptl_absorpt_correction_T_max  0.985
_exptl_absorpt_correction_T_min  0.931
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
        CrysAlisPro 1.171.40.67a (Rigaku Oxford Diffraction, 2019)
Analytical numeric absorption correction using a multifaceted crystal
                        model based on expressions derived by R.C. Clark & J.S.
        (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.466
_exptl_crystal_description       prism
_exptl_crystal_F_000             534
_exptl_crystal_size_max          0.407
_exptl_crystal_size_mid          0.073
_exptl_crystal_size_min          0.058
_refine_diff_density_max         0.407
_refine_diff_density_min         -0.432
_refine_diff_density_rms         0.08
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     343
_refine_ls_number_reflns         4588
_refine_ls_number_restraints     38
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.1205
_refine_ls_R_factor_gt           0.0679
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0346P)^2^+0.2450P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1186
_refine_ls_wR_factor_ref         0.1502
_reflns_Friedel_coverage         0
_reflns_number_gt                2749
_reflns_number_total             4588
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ob02176a2.cif
_cod_data_source_block           a20210181_csa637
_cod_depositor_comments          'Adding full bibliography for 7158456.cif.'
_cod_original_cell_volume        1166.1(2)
_cod_original_formula_sum        'C25 H23 F3 N O3.50 S2'
_cod_database_code               7158456