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_7158753
_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         'C26 H32 N2 O4 S2'
_chemical_formula_sum            'C26 H32 N2 O4 S2'
_chemical_formula_weight         500.65
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2022-05-05
_audit_creation_method
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6429)
;
_audit_update_record
;
2022-05-11 deposited with the CCDC.	2022-06-29 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   13.6854(3)
_cell_length_b                   17.3409(3)
_cell_length_c                   22.5373(3)
_cell_measurement_reflns_used    8343
_cell_measurement_temperature    292.3(2)
_cell_measurement_theta_max      78.6880
_cell_measurement_theta_min      3.9100
_cell_volume                     5348.49(17)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      292.3(2)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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      2.00  27.00   0.50    1.25    --    0.00 -57.00-150.00   50
  2  \w    -89.00  -2.00   0.50    1.25    --    0.00 -57.00-150.00  174
  3  \w    -63.00 -28.00   0.50    1.25    --    0.00 -57.00   0.00   70
  4  \w     52.00  78.00   0.50    1.25    --    0.00  57.00  30.00   52
  5  \w     19.00 107.00   0.50    9.00    --  106.20 -61.00  90.00  176
  6  \w     43.00  87.00   0.50    9.00    --  106.20 -61.00 -30.00   88
  7  \w    103.00 196.00   0.50    9.00    --  106.20  30.00-150.00  186
  8  \w     18.00  60.00   0.50    9.00    --  106.20 -30.00 -30.00   84
  9  \w    151.00 188.00   0.50    9.00    --  106.20  45.00 120.00   74
 10  \w     69.00  94.00   0.50    9.00    --  106.20 -30.00 -30.00   50
 11  \w     90.00 135.00   0.50    9.00    --  106.20 -45.00 -60.00   90
 12  \w    148.00 173.00   0.50    9.00    --  106.20  45.00-120.00   50
 13  \w     20.00  69.00   0.50    9.00    --  106.20 -45.00 -60.00   98
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa dual home/near'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0912769000
_diffrn_orient_matrix_UB_12      0.0514635000
_diffrn_orient_matrix_UB_13      0.0051539000
_diffrn_orient_matrix_UB_21      0.0046435000
_diffrn_orient_matrix_UB_22      -0.0064141000
_diffrn_orient_matrix_UB_23      0.0681280000
_diffrn_orient_matrix_UB_31      0.0656794000
_diffrn_orient_matrix_UB_32      0.0721377000
_diffrn_orient_matrix_UB_33      0.0024306000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0370
_diffrn_reflns_av_unetI/netI     0.0323
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            20105
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        65.080
_diffrn_reflns_theta_max         65.080
_diffrn_reflns_theta_min         3.923
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.073
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.62041
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.244
_exptl_crystal_description       block
_exptl_crystal_F_000             2128
_refine_diff_density_max         0.323
_refine_diff_density_min         -0.261
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     340
_refine_ls_number_reflns         4561
_refine_ls_number_restraints     108
_refine_ls_restrained_S_all      1.105
_refine_ls_R_factor_all          0.0496
_refine_ls_R_factor_gt           0.0436
_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^)+(0.0797P)^2^+1.0841P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1294
_refine_ls_wR_factor_ref         0.1354
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3899
_reflns_number_total             4561
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ob01034h2.cif
_cod_data_source_block           mxt-20220504
_cod_database_code               7158753
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C S N H O'
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C2-C1A = C3-C2 = C3A-C2A = C2A-C1 = C1-C00P = C1A-C00P
 1.53 with sigma of 0.02
 C3-C1A
 2.2 with sigma of 0.02
 C1A-C00P = C1-C00P
 1.53 with sigma of 0.02
 C2-C3 \\sim C2A-C3A
 with sigma of 0.02
 C00P-C1 \\sim C00P-C1A
 with sigma of 0.02
 C1-C2 \\sim C1A-C2A
 with sigma of 0.02
 C1-C3 \\sim C1A-C3A
 with sigma of 0.04
 C00P-C2 \\sim C00P-C2A
 with sigma of 0.04
3. Rigid bond restraints
 C1, C2, C3, C1A, C2A, C3A
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
C1A \\sim C1 \\sim C2 \\sim C2A \\sim C3 \\sim C3A: within 3.8A with sigma of
0.01 and sigma for terminal atoms of 0.03 within 3.8A
C3 \\sim C3A: within 3.8A with sigma of 0.01 and sigma for terminal atoms of
0.03 within 3.8A
5. Others
 Sof(H00A)=Sof(H00B)=Sof(C1A)=Sof(H1AA)=Sof(H1AB)=Sof(C2A)=Sof(H2AA)=Sof(H2AB)=
 Sof(C3A)=Sof(H3AA)=Sof(H3AB)=Sof(H3AC)=1-FVAR(1)
 Sof(H00C)=Sof(H00E)=Sof(C1)=Sof(H1A)=Sof(H1B)=Sof(C2)=Sof(H2A)=Sof(H2B)=
 Sof(C3)=Sof(H3A)=Sof(H3B)=Sof(H3C)=FVAR(1)
6.a Secondary CH2 refined with riding coordinates:
 C00P(H00C,H00E), C00P(H00A,H00B), C00Q(H00F,H00G), C00S(H00P,H00Q), C00T(H00R,
 H00S), C1(H1A,H1B), C2(H2A,H2B), C1A(H1AA,H1AB), C2A(H2AA,H2AB)
6.b Aromatic/amide H refined with riding coordinates:
 N007(H007), N008(H008), C00D(H00D), C00J(H00J), C00K(H00K), C00L(H00L),
 C00M(H00M), C00N(H00N)
6.c Idealised Me refined as rotating group:
 C00R(H00H,H00I,H00O), C00U(H00T,H00U,H00V), C00W(H00W,H00X,H00Y), C3(H3A,H3B,
 H3C), C3A(H3AA,H3AB,H3AC)
;
_shelx_res_checksum              39148
_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 1.577
_oxdiff_exptl_absorpt_empirical_full_min 0.760