Synthesis of deuteriodifluoromethylthiolated isocoumarins-1-imines and isocoumarins enabled by multi-component reagents system (MCRS).
Li, Xuemin; Shi, Haofeng; He, Jiaxin; Wu, Jialiang; Sun, Fengxia; Du, Yunfei; Organic & biomolecular chemistry 22 (2024) 3882–3886; doi:10.1039/d4ob00328d

data_7159910
_publ_section_title
;
 Synthesis of deuteriodifluoromethylthiolated isocoumarins-1-imines and
 isocoumarins enabled by multi-component reagents system (MCRS).
;
_journal_issue                   19
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              3882
_journal_page_last               3886
_journal_paper_doi               10.1039/d4ob00328d
_journal_volume                  22
_journal_year                    2024
_chemical_formula_moiety         'C23 H17 F2 N O3 S2'
_chemical_formula_sum            'C23 H17 F2 N O3 S2'
_chemical_formula_weight         457.49
_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             2023-06-02
_audit_creation_method
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_audit_update_record
;
2023-06-02 deposited with the CCDC.	2024-04-19 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 104.2530(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.09300(10)
_cell_length_b                   19.0071(2)
_cell_length_c                   8.60340(10)
_cell_measurement_reflns_used    21616
_cell_measurement_temperature    301.54(10)
_cell_measurement_theta_max      75.2800
_cell_measurement_theta_min      2.3400
_cell_volume                     2075.14(4)
_computing_cell_refinement       'CrysAlisPro 1.171.42.63a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.63a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.63a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      301.54(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.976
_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    -26.00  71.00   0.50    0.05    --   45.63 -77.00 150.00  194
  2  \w     37.00  64.00   0.50    0.05    --  104.81 -61.00  90.00   54
  3  \w     32.00 102.00   0.50    0.05    --  104.81 -77.00-120.00  140
  4  \w    -26.00  64.00   0.50    0.05    --   45.63 -61.00-149.00  180
  5  \w     32.00  68.00   0.50    0.05    --  104.81 -61.00-149.00   72
  6  \w     33.00  67.00   0.50    0.05    --  104.81 -61.00 150.00   68
  7  \w     86.00 175.00   0.50    0.05    --  104.81  61.00 -11.00  178
  8  \w     84.00 175.00   0.50    0.05    --  104.81  15.00 -90.00  182
  9  \w     86.00 175.00   0.50    0.05    --  104.81  61.00 -90.00  178
 10  \w     86.00 172.00   0.50    0.05    --  104.81  61.00 150.00  172
 11  \w     88.00 175.00   0.50    0.05    --  104.81  45.00 120.00  174
 12  \w     27.00 119.00   0.50    0.05    --   45.63  61.00 -11.00  184
 13  \w     29.00 119.00   0.50    0.05    --   45.63  57.00  60.00  180
 14  \w     27.00 123.00   0.50    0.05    --   45.63  19.00-180.00  192
 15  \w     17.00  93.00   0.50    0.05    --   45.63-125.00  30.00  152
 16  \w    -29.00  32.00   0.50    0.05    --  -45.63  19.00 -30.00  122
 17  \w    -64.00  28.00   0.50    0.05    --  -45.63  61.00 -11.00  184
 18  \w   -108.00 -27.00   0.50    0.05    -- -100.00  77.00 -90.00  162
 19  \w   -108.00 -27.00   0.50    0.05    -- -100.00  77.00-150.00  162
 20  \w    -74.00 -27.00   0.50    0.05    -- -100.00  61.00 -11.00   94
 21  \w    -54.00 -27.00   0.50    0.05    -- -100.00  45.00 -30.00   54
 22  \w   -108.00 -27.00   0.50    0.05    -- -100.00  77.00  60.00  162
 23  \w    -54.00 -27.00   0.50    0.05    -- -100.00  45.00  30.00   54
 24  \w    -54.00 -27.00   0.50    0.05    -- -100.00  45.00   0.00   54
 25  \w    -54.00 -27.00   0.50    0.05    -- -100.00  45.00  60.00   54
 26  \w    -74.00 -27.00   0.50    0.05    -- -100.00  61.00 120.00   94
 27  \w    -54.00 -27.00   0.50    0.05    -- -100.00  45.00 150.00   54
 28  \w    -54.00 -27.00   0.50    0.05    -- -100.00  45.00 120.00   54
 29  \w   -177.00 -79.00   0.50    0.05    -- -100.00 -15.00  90.00  196
 30  \w   -173.00 -81.00   0.50    0.05    -- -100.00 -61.00 150.00  184
 31  \w   -173.00 -81.00   0.50    0.05    -- -100.00 -61.00 120.00  184
 32  \w   -173.00 -83.00   0.50    0.05    -- -100.00 -45.00  90.00  180
 33  \w   -173.00 -83.00   0.50    0.05    -- -100.00 -45.00  60.00  180
 34  \w   -175.00 -83.00   0.50    0.05    -- -100.00 -30.00 150.00  184
 35  \w   -175.00 -83.00   0.50    0.05    -- -100.00 -30.00  60.00  184
 36  \w   -173.00 -81.00   0.50    0.05    -- -100.00 -61.00 -60.00  184
 37  \w   -119.00 -27.00   0.50    0.05    --  -45.63 -61.00-149.00  184
 38  \w   -173.00 -81.00   0.50    0.05    -- -100.00 -61.00-149.00  184
 39  \w   -170.00 -82.00   0.50    0.05    -- -100.00-125.00-120.00  176
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom system, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1203073000
_diffrn_orient_matrix_UB_12      0.0095286000
_diffrn_orient_matrix_UB_13      0.0568248000
_diffrn_orient_matrix_UB_21      0.0046922000
_diffrn_orient_matrix_UB_22      -0.0580059000
_diffrn_orient_matrix_UB_23      0.1266022000
_diffrn_orient_matrix_UB_31      0.0156797000
_diffrn_orient_matrix_UB_32      -0.0558021000
_diffrn_orient_matrix_UB_33      -0.1219222000
_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  0.0277
_diffrn_reflns_av_unetI/netI     0.0134
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            38596
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.274
_diffrn_reflns_theta_min         4.189
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.718
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.73282
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.63a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'light colourless'
_exptl_crystal_density_diffrn    1.464
_exptl_crystal_description       block
_exptl_crystal_F_000             944
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_refine_diff_density_max         1.492
_refine_diff_density_min         -0.483
_refine_diff_density_rms         0.065
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.090
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     281
_refine_ls_number_reflns         4194
_refine_ls_number_restraints     186
_refine_ls_restrained_S_all      1.208
_refine_ls_R_factor_all          0.0770
_refine_ls_R_factor_gt           0.0722
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1264P)^2^+1.3218P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2244
_refine_ls_wR_factor_ref         0.2296
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3708
_reflns_number_total             4194
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ob00328d2.cif
_cod_data_source_block           exp_878lxm-scf2d_auto
_cod_depositor_comments          'Adding full bibliography for 7159910.cif.'
_cod_database_code               7159910
_shelx_shelxl_version_number     2018/1
_reflns_odcompleteness_completeness 99.95
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Uiso/Uaniso restraints and constraints
All non-hydrogen atoms restrained to be isotropic: with sigma of 0.005 and
sigma for terminal atoms of 0.01
2.a Ternary CH refined with riding coordinates:
 C8(H8)
2.b Aromatic/amide H refined with riding coordinates:
 C59(H59), C50(H50), C56(H56), C60(H60), C57(H57), C35(H35), C15(H15),
 C17(H17), C20(H20), C22(H22), C24(H24), C26(H26), C28(H28)
2.c Idealised Me refined as rotating group:
 C30(H30A,H30B,H30C)
;
_shelx_res_checksum              56631
_shelx_hkl_checksum              44561
_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 1.638
_oxdiff_exptl_absorpt_empirical_full_min 0.734