Synthesis of 3-amino-substituted benzothiadiazine oxides by a palladium-catalysed cascade reaction
Hommelsheim, Renè; Bausch, Sandra; van Nahl, Robin; Ward, Jas S.; Rissanen, Kari; Bolm, Carsten; Green Chemistry 25 (2023) 3021–3026; doi:10.1039/D3GC00442B

data_7246497
_publ_section_title
;
 Synthesis of 3-amino-substituted benzothiadiazine oxides by a
 palladium-catalysed cascade reaction
;
_journal_issue                   8
_journal_name_full               'Green Chemistry'
_journal_page_first              3021
_journal_page_last               3026
_journal_paper_doi               10.1039/D3GC00442B
_journal_volume                  25
_journal_year                    2023
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C14 H12 Cl N3 O S'
_chemical_formula_sum            'C14 H12 Cl N3 O S'
_chemical_formula_weight         305.78
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2023-02-06
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2023-02-06 deposited with the CCDC.	2023-03-21 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 106.910(5)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   10.7651(5)
_cell_length_b                   4.8762(2)
_cell_length_c                   13.0778(5)
_cell_measurement_reflns_used    1480
_cell_measurement_temperature    120.01(10)
_cell_measurement_theta_max      75.6750
_cell_measurement_theta_min      4.2440
_cell_volume                     656.81(5)
_computing_cell_refinement       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_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_environment      N~2~
_diffrn_ambient_temperature      120.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1947
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.987
_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   -112.00 -74.00   1.00    2.00    --  -42.17-143.00 -26.00   38
  2  \w   -116.00 -18.00   1.00    2.00    --  -42.17 -37.00-150.00   98
  3  \w     37.00  90.00   1.00    2.00    --   42.17-125.00  60.00   53
  4  \w    -20.00   8.00   1.00    2.00    --   42.17 -77.00-180.00   28
  5  \w     50.00  75.00   1.00    2.00    --   42.17 -77.00-180.00   25
  6  \w     35.00 107.00   1.00    5.00    --  112.00 -94.00 120.00   72
  7  \w     86.00 171.00   1.00    5.00    --  112.00  45.00-120.00   85
  8  \w     63.00 137.00   1.00    5.00    --  112.00 -61.00 150.00   74
  9  \w     70.00 109.00   1.00    5.00    --  112.00-111.00 -90.00   39
 10  \w     85.00 129.00   1.00    5.00    --  112.00  30.00  30.00   44
 11  \w     39.00  91.00   1.00    5.00    --  112.00 -45.00 120.00   52
 12  \w    105.00 177.00   1.00    5.00    --  112.00 111.00-180.00   72
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0058186000
_diffrn_orient_matrix_UB_12      0.3154424000
_diffrn_orient_matrix_UB_13      0.0041693000
_diffrn_orient_matrix_UB_21      0.1323648000
_diffrn_orient_matrix_UB_22      0.0039142000
_diffrn_orient_matrix_UB_23      0.0865646000
_diffrn_orient_matrix_UB_31      0.0693917000
_diffrn_orient_matrix_UB_32      0.0192185000
_diffrn_orient_matrix_UB_33      -0.0874342000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0303
_diffrn_reflns_av_unetI/netI     0.0539
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            2727
_diffrn_reflns_point_group_measured_fraction_full 0.770
_diffrn_reflns_point_group_measured_fraction_max 0.745
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.346
_diffrn_reflns_theta_min         3.532
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    4.050
_exptl_absorpt_correction_T_max  0.939
_exptl_absorpt_correction_T_min  0.604
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.546
_exptl_crystal_description       needle
_exptl_crystal_F_000             316
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: dichloromethane/pentane'
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.043
_exptl_crystal_size_min          0.015
_refine_diff_density_max         0.461
_refine_diff_density_min         -0.337
_refine_diff_density_rms         0.078
_refine_ls_abs_structure_details
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   -0.03(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     185
_refine_ls_number_reflns         2001
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0473
_refine_ls_R_factor_gt           0.0431
_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^)+(0.0648P)^2^+0.1921P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1078
_refine_ls_wR_factor_ref         0.1119
_reflns_Friedel_coverage         0.344
_reflns_Friedel_fraction_full    0.478
_reflns_Friedel_fraction_max     0.434
_reflns_number_gt                1877
_reflns_number_total             2001
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3gc00442b2.cif
_cod_data_source_block           3ak
_cod_depositor_comments          'Adding full bibliography for 7246497.cif.'
_cod_database_code               7246497
_shelxl_version_number           2014/6
_shelx_estimated_absorpt_t_max   0.942
_shelx_estimated_absorpt_t_min   0.469
_reflns_odcompleteness_completeness 98.74
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C8(H8), C9(H9), C15(H15), C16(H16), C18(H18), C19(H19)
2.b Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C)
;
_shelx_res_checksum              77362
_ins_header
;
TITL RH-P894-b3_numabs_ana in P2(1) 
REM P2(1) (#4 in standard setting)
CELL 1.54184  10.765143   4.876245  13.077758  90.0000 106.9095  90.0000
ZERR    2.00   0.000494   0.000218   0.000532   0.0000   0.0047   0.0000
LATT -1
SYMM -x, y+1/2,-z 
SFAC C H N O S Cl
UNIT 28.00 24.00 6.00 2.00 2.00 2.00
TREF
HKLF 4
END
;
_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 1.351
_oxdiff_exptl_absorpt_empirical_full_min 0.743