Sustainable access to benzothiophene derivatives bearing a trifluoromethyl group via a three-component domino reaction in water
Deng, Qingsong; Gu, Jun; Zhang, Huan; Zhang, Youlai; Meng, Xiangtai; Organic & Biomolecular Chemistry  (2022) –; doi:10.1039/D2OB01034H

data_7158751
_publ_section_title
;
 Sustainable access to benzothiophene derivatives bearing a
 trifluoromethyl group via a three-component domino reaction in water
;
_journal_name_full               'Organic &amp; Biomolecular Chemistry'
_journal_paper_doi               10.1039/D2OB01034H
_journal_year                    2022
_chemical_formula_moiety         'C25 H23 F3 N2 O S'
_chemical_formula_sum            'C25 H23 F3 N2 O S'
_chemical_formula_weight         456.51
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2020-09-11
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-10-03 deposited with the CCDC.	2022-06-29 downloaded from the CCDC.
;
_cell_angle_alpha                87.735(8)
_cell_angle_beta                 77.519(9)
_cell_angle_gamma                65.425(9)
_cell_formula_units_Z            2
_cell_length_a                   8.9308(9)
_cell_length_b                   9.8192(9)
_cell_length_c                   14.3606(17)
_cell_measurement_reflns_used    2282
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.2300
_cell_measurement_theta_min      3.4500
_cell_volume                     1116.4(2)
_computing_cell_refinement       'CrysAlisPro 1.171.39.7e (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.7e (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.7e (Rigaku OD, 2015)'
_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      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.852
_diffrn_measured_fraction_theta_max 0.852
_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      8.00  34.00   1.00   26.24    --   30.00  54.00  90.00   26
  2  \w    -74.00 108.00   1.00   26.24    --   30.00  54.00-150.00  182
  3  \w    -70.00  58.00   1.00   26.24    --   30.00  54.00 -30.00  128
  4  \w    -73.00 -48.00   1.00   26.24    --   30.00  54.00  90.00   25
;
_diffrn_measurement_device       'two-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Mini (ROW)'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0764309000
_diffrn_orient_matrix_UB_12      -0.0129325000
_diffrn_orient_matrix_UB_13      0.0135321000
_diffrn_orient_matrix_UB_21      0.0324485000
_diffrn_orient_matrix_UB_22      0.0176793000
_diffrn_orient_matrix_UB_23      -0.0461521000
_diffrn_orient_matrix_UB_31      -0.0334562000
_diffrn_orient_matrix_UB_32      0.0764839000
_diffrn_orient_matrix_UB_33      0.0159453000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0772
_diffrn_reflns_av_unetI/netI     0.1020
_diffrn_reflns_Laue_measured_fraction_full 0.852
_diffrn_reflns_Laue_measured_fraction_max 0.852
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            5196
_diffrn_reflns_point_group_measured_fraction_full 0.852
_diffrn_reflns_point_group_measured_fraction_max 0.852
_diffrn_reflns_theta_full        24.713
_diffrn_reflns_theta_max         24.713
_diffrn_reflns_theta_min         2.638
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.190
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.47756
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.7e (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.358
_exptl_crystal_description       block
_exptl_crystal_F_000             476
_refine_diff_density_max         0.522
_refine_diff_density_min         -0.279
_refine_diff_density_rms         0.064
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.930
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     292
_refine_ls_number_reflns         3238
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.930
_refine_ls_R_factor_all          0.1238
_refine_ls_R_factor_gt           0.0819
_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^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2300
_refine_ls_wR_factor_ref         0.2791
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2181
_reflns_number_total             3238
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ob01034h2.cif
_cod_data_source_block           5
_cod_database_code               7158751
_shelx_shelxl_version_number     2017/1
_reflns_odcompleteness_completeness 99.91
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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 Secondary CH2 refined with riding coordinates:
 C009(H00A,H00B), C00O(H00E,H00F), C00P(H00G,H00I)
2.b Aromatic/amide H refined with riding coordinates:
 C00B(H00C), C00C(H00D), C00H(H00H), C00J(H00J), C00K(H00K), C00L(H00L),
 C4(H4), C0AA(H0AA)
2.c Idealised Me refined as rotating group:
 C00Q(H00M,H00N,H00O), C00R(H00P,H00Q,H00R), C00S(H00S,H00T,H00U)
;
_shelx_res_checksum              40843
_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 1.488
_oxdiff_exptl_absorpt_empirical_full_min 0.736