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_7158750
_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         'C16 H16 F3 N O2 S'
_chemical_formula_sum            'C16 H16 F3 N O2 S'
_chemical_formula_weight         343.36
_chemical_name_systematic        555
_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             2019-12-20
_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                 110.597(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.9152(6)
_cell_length_b                   13.5262(4)
_cell_length_c                   10.7286(6)
_cell_measurement_reflns_used    5595
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      67.1790
_cell_measurement_theta_min      3.9700
_cell_volume                     1618.57(15)
_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 (Sheldrick, 2015)'
_diffrn_ambient_temperature      293
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_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     60.00 129.00   0.50    3.28    --   40.70  32.00  60.00  138
  2  \w     34.00  65.00   0.50    3.28    --   40.70 -65.00  60.00   62
  3  \w    -19.00  52.00   0.50    3.28    --   40.70 -77.00 -30.00  142
  4  \w     16.00 130.00   0.50    3.28    --   40.70  65.00-150.00  228
  5  \w     34.00  60.00   0.50    3.28    --   40.70 -82.00-150.00   52
  6  \w     37.00  64.00   0.50    3.28    --   40.70 -82.00-180.00   54
  7  \w     35.00  63.00   0.50    3.28    --   40.70 -65.00-120.00   56
  8  \w     12.00  66.00   0.50    3.28    --   40.70 -82.00-120.00  108
  9  \w     22.00  49.00   0.50    3.28    --   40.70  77.00  60.00   54
 10  \w     -2.00  24.00   0.50    3.28    --   40.70 -82.00-180.00   52
 11  \w     55.00 129.00   0.50    3.28    --   40.70  82.00 -90.00  148
 12  \w    -22.00   4.00   0.50    3.28    --   40.70 -65.00 -60.00   52
 13  \w    -47.00   2.00   0.50    3.28    --   40.70 -82.00-150.00   98
 14  \w    -36.00  20.00   0.50    3.28    --   40.70 -82.00  30.00  112
 15  \w     13.00  46.00   0.50    3.28    --   40.70  32.00  60.00   66
 16  \w     36.00  67.00   0.50    3.28    --   40.70 -82.00  30.00   62
 17  \w     -5.00  30.00   0.50    3.28    --   40.70 -65.00-120.00   70
 18  \w    -37.00 -12.00   0.50    3.28    --   40.70 -65.00-120.00   50
 19  \w    -43.00 -18.00   0.50    3.28    --   40.70 -82.00-180.00   50
 20  \w     78.00 104.00   0.50    3.28    --   40.70  77.00  60.00   52
 21  \w     -5.00  32.00   0.50    3.28    --   40.70 -65.00  60.00   74
 22  \w     33.00  93.00   0.50    6.14    --   93.40 -82.00 -60.00  120
 23  \w      6.00  48.00   0.50    6.14    --   93.40 -25.00  90.00   84
 24  \w      5.00 171.00   0.50    6.14    --   93.40   0.00-120.00  332
 25  \w     11.00  99.00   0.50    6.14    --   93.40 -82.00 120.00  176
 26  \w      4.00  99.00   0.50    6.14    --   93.40 -82.00-120.00  190
 27  \w     59.00  97.00   0.50    6.14    --   93.40 -82.00  60.00   76
 28  \w      8.00 113.00   0.50    6.14    --   93.40 -33.00 -30.00  210
 29  \w     55.00  81.00   0.50    6.14    --   93.40 -25.00  90.00   52
 30  \w     95.00 135.00   0.50    6.14    --   93.40 -25.00  90.00   80
 31  \w     23.00 101.00   0.50    6.14    --   93.40 -82.00 150.00  156
 32  \w      6.00  46.00   0.50    6.14    --   93.40 -82.00 -90.00   80
 33  \w     93.00 130.00   0.50    6.14    --   93.40  33.00  60.00   74
 34  \w     12.00  87.00   0.50    6.14    --   93.40 -82.00-150.00  150
 35  \w     83.00 133.00   0.50    6.14    --   93.40 -33.00 150.00  100
 36  \w     66.00 107.00   0.50    6.14    --   93.40  59.00 -60.00   82
 37  \w      5.00 120.00   0.50    6.14    --   93.40 -59.00 -30.00  230
 38  \w     74.00 118.00   0.50    6.14    --   93.40 -82.00   0.00   88
 39  \w     42.00  93.00   0.50    6.14    --   93.40 -82.00  90.00  102
 40  \w    154.00 179.00   0.50    6.14    --   93.40 -25.00  90.00   50
 41  \w      4.00  79.00   0.50    6.14    --   93.40 -82.00-180.00  150
 42  \w     61.00  97.00   0.50    6.14    --   93.40 -82.00 -90.00   72
 43  \w      9.00  94.00   0.50    6.14    --   93.40 -82.00 -30.00  170
;
_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      -0.1344479000
_diffrn_orient_matrix_UB_12      -0.0049869000
_diffrn_orient_matrix_UB_13      -0.0851819000
_diffrn_orient_matrix_UB_21      0.0136281000
_diffrn_orient_matrix_UB_22      0.0923311000
_diffrn_orient_matrix_UB_23      -0.0775523000
_diffrn_orient_matrix_UB_31      0.0287599000
_diffrn_orient_matrix_UB_32      -0.0665306000
_diffrn_orient_matrix_UB_33      -0.1013066000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0395
_diffrn_reflns_av_unetI/netI     0.0343
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            12854
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         67.719
_diffrn_reflns_theta_min         3.963
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.149
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.57283
_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    1.409
_exptl_crystal_description       plate
_exptl_crystal_F_000             712
_exptl_crystal_size_max          0.06
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.193
_refine_diff_density_min         -0.371
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     211
_refine_ls_number_reflns         2912
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.065
_refine_ls_R_factor_all          0.0587
_refine_ls_R_factor_gt           0.0479
_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^)+(0.0847P)^2^+0.2757P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1358
_refine_ls_wR_factor_ref         0.1462
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2268
_reflns_number_total             2912
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ob01034h2.cif
_cod_data_source_block           exp_32
_cod_original_cell_volume        1618.57(14)
_cod_database_code               7158750
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.958
_shelx_estimated_absorpt_t_min   0.882
_diffrn_oxdiff_digest_frames
;
018c683d82c8b9dcf04e80dbc771e8d00204604e121
;
_diffrn_oxdiff_digest_hkl
;
015b95a0e602ef3cb6a497e758a84ede10db82
;
_reflns_odcompleteness_completeness 99.87
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.49
_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, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C00I(H00A,H00B), C00J(H00C,H00E), C00M(H00K,H00L)
2.b Aromatic/amide H refined with riding coordinates:
 C00D(H00D), C00F(H00F), C00H(H00H)
2.c Idealised Me refined as rotating group:
 C00K(H00G,H00I,H00J), C00N(H00M,H00N,H00O)
2.d Idealised tetrahedral OH refined as rotating group:
 O006(H006)
;
_shelx_res_checksum              77920
_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 2.046
_oxdiff_exptl_absorpt_empirical_full_min 0.557