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_7158752
_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         'C15 H14 F3 N O2 S'
_chemical_formula_sum            'C15 H14 F3 N O2 S'
_chemical_formula_weight         329.33
_chemical_name_systematic        2
_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
_audit_creation_date             2020-08-26
_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                90
_cell_angle_beta                 99.649(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.0814(2)
_cell_length_b                   8.8689(2)
_cell_length_c                   19.9409(4)
_cell_measurement_reflns_used    6537
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      67.1340
_cell_measurement_theta_min      2.3090
_cell_volume                     1583.36(6)
_computing_cell_refinement       'CrysAlisPro 1.171.41.43a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.41.43a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.41.43a (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 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      293
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.966
_diffrn_measured_fraction_theta_max 0.966
_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     61.00 129.00   0.50    0.50    --   40.90  82.00-120.00  136
  2  \w     23.00  62.00   0.50    0.50    --   40.90 -77.00 -60.00   78
  3  \w     17.00  56.00   0.50    0.50    --   40.90  82.00-120.00   78
  4  \w    -39.00  -1.00   0.50    0.50    --   40.90 -54.00 -60.00   76
  5  \w     19.00  67.00   0.50    0.50    --   40.90 -82.00 120.00   96
  6  \w     16.00 130.00   0.50    0.50    --   40.90  65.00-180.00  228
  7  \w     21.00  65.00   0.50    0.50    --   40.90 -82.00 -90.00   88
  8  \w     30.00  64.00   0.50    0.50    --   40.90 -82.00   0.00   68
  9  \w    -21.00  51.00   0.50    0.50    --   40.90 -77.00-120.00  144
 10  \w      7.00  67.00   0.50    0.50    --   40.90 -54.00 -60.00  120
 11  \w    -47.00 -21.00   0.50    0.50    --   40.90 -82.00-180.00   52
 12  \w     29.00  59.00   0.50    0.50    --   40.90 -82.00-180.00   60
 13  \w    -15.00  10.00   0.50    0.50    --   40.90 -82.00 120.00   50
 14  \w    102.00 128.00   0.50    0.50    --   40.90  54.00  30.00   52
 15  \w     55.00  83.00   0.50    0.50    --   40.90  54.00  30.00   56
 16  \w     74.00 111.00   0.50    0.50    --   40.90  77.00  90.00   74
 17  \w     20.00  67.00   0.50    0.50    --   40.90  77.00  90.00   94
 18  \w     80.00 116.00   0.50    0.50    --   40.90  65.00 -30.00   72
 19  \w     39.00  64.00   0.50    0.50    --   40.90 -77.00   0.00   50
 20  \w     54.00 116.00   0.50    0.50    --   93.40 -82.00 120.00  124
 21  \w     55.00 136.00   0.50    0.50    --   93.40  33.00 -90.00  162
 22  \w     71.00  97.00   0.50    0.50    --   93.40  50.00 120.00   52
 23  \w     15.00 127.00   0.50    0.50    --   93.40 -50.00  60.00  224
 24  \w      4.00  95.00   0.50    0.50    --   93.40 -82.00  30.00  182
 25  \w      6.00 119.00   0.50    0.50    --   93.40 -82.00 -90.00  226
 26  \w     75.00 101.00   0.50    0.50    --   93.40 -82.00  90.00   52
 27  \w      4.00  62.00   0.50    0.50    --   93.40 -82.00 -30.00  116
 28  \w     71.00  97.00   0.50    0.50    --   93.40 -82.00 -30.00   52
 29  \w      4.00  41.00   0.50    0.50    --   93.40 -77.00   0.00   74
 30  \w      8.00  33.00   0.50    0.50    --   93.40 -82.00   0.00   50
 31  \w     54.00  99.00   0.50    0.50    --   93.40  33.00 -30.00   90
 32  \w     43.00  91.00   0.50    0.50    --   93.40 -82.00-180.00   96
 33  \w     32.00  90.00   0.50    0.50    --   93.40 -82.00-120.00  116
 34  \w     86.00 116.00   0.50    0.50    --   93.40 -59.00 -90.00   60
 35  \w      9.00  95.00   0.50    0.50    --   93.40 -82.00-150.00  172
 36  \w     47.00 182.00   0.50    0.50    --   93.40   0.00-180.00  270
 37  \w     31.00  66.00   0.50    0.50    --   93.40 -59.00 -90.00   70
 38  \w     76.00 102.00   0.50    0.50    --   93.40 -82.00 -60.00   52
 39  \w     85.00 110.00   0.50    0.50    --   93.40 -82.00 150.00   50
 40  \w    138.00 163.00   0.50    0.50    --   93.40  50.00 120.00   50
 41  \w      4.00  90.00   0.50    0.50    --   93.40 -82.00  60.00  172
 42  \w     72.00  97.00   0.50    0.50    --   93.40 -82.00   0.00   50
 43  \w    132.00 182.00   0.50    0.50    --   93.40  25.00-150.00  100
 44  \w     11.00 118.00   0.50    0.50    --   93.40  25.00-150.00  214
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Pro II AFC12 (RINC): Kappa single'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1202388000
_diffrn_orient_matrix_UB_12      -0.0944190000
_diffrn_orient_matrix_UB_13      -0.0266976000
_diffrn_orient_matrix_UB_21      0.0768748000
_diffrn_orient_matrix_UB_22      0.1457789000
_diffrn_orient_matrix_UB_23      -0.0180973000
_diffrn_orient_matrix_UB_31      0.0960782000
_diffrn_orient_matrix_UB_32      0.0017194000
_diffrn_orient_matrix_UB_33      0.0714446000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0350
_diffrn_reflns_av_unetI/netI     0.0267
_diffrn_reflns_Laue_measured_fraction_full 0.966
_diffrn_reflns_Laue_measured_fraction_max 0.966
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            13223
_diffrn_reflns_point_group_measured_fraction_full 0.966
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_theta_full        67.516
_diffrn_reflns_theta_max         67.516
_diffrn_reflns_theta_min         4.498
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.173
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.27971
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.43a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear whiteish colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.382
_exptl_crystal_description       block
_exptl_crystal_F_000             680
_exptl_crystal_size_max          0.06
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.196
_refine_diff_density_min         -0.263
_refine_diff_density_rms         0.032
_refine_ls_extinction_coef       0.0019(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     204
_refine_ls_number_reflns         2747
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.087
_refine_ls_R_factor_all          0.0419
_refine_ls_R_factor_gt           0.0374
_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^)+(0.0576P)^2^+0.1878P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1090
_refine_ls_wR_factor_ref         0.1126
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2373
_reflns_number_total             2747
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ob01034h2.cif
_cod_data_source_block           exp_344-02
_cod_database_code               7158752
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.958
_shelx_estimated_absorpt_t_min   0.881
_diffrn_oxdiff_digest_frames
;
01dd14decb1c8ca3bc671b33f465a8601200029e285
;
_diffrn_oxdiff_digest_hkl
;
01cc189c4160246eba244f8669136ebe343ca2
;
_reflns_odcompleteness_completeness 96.44
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.49
_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, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C19(H19)
2.b Aromatic/amide H refined with riding coordinates:
 C8(H8), C6(H6), C5(H5)
2.c Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C), C20(H20A,H20B,H20C), C22(H22A,H22B,H22C)
2.d Idealised tetrahedral OH refined as rotating group:
 O17(H17)
;
_shelx_res_checksum              188
_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 3.843
_oxdiff_exptl_absorpt_empirical_full_min 0.468