Palladium(0)-catalysed regioselective cyclisations of 2-amino(tosyl) benzamides/sulphonamides: the stereoselective synthesis of 3-ylidene-[1,4]benzodiazepin-5-ones/benzo[<i>f</i>][1,2,5]thiadiazepine-1,1-dioxides.
Mondal, Debasmita; Pal, Gargi; Chowdhury, Chinmay; Chemical communications (Cambridge, England) 57 (2021) 5462–5465; doi:10.1039/d1cc00793a

data_7128282
_publ_section_title
;
 Palladium(0)-catalysed regioselective cyclisations of 2-amino(tosyl)
 benzamides/sulphonamides: the stereoselective synthesis of
 3-ylidene-[1,4]benzodiazepin-5-ones/benzo[<i>f</i>][1,2,5]thiadiazepine-1,1-dioxides.
;
_journal_issue                   44
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              5462
_journal_page_last               5465
_journal_paper_doi               10.1039/d1cc00793a
_journal_volume                  57
_journal_year                    2021
_chemical_formula_moiety         'C22 H17 Cl N2 O'
_chemical_formula_sum            'C22 H17 Cl N2 O'
_chemical_formula_weight         360.82
_chemical_name_systematic        DM-3-84
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2021-02-01
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-02-10 deposited with the CCDC.	2021-04-26 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.4364(17)
_cell_length_b                   12.3676(18)
_cell_length_c                   14.215(2)
_cell_measurement_reflns_used    9622
_cell_measurement_temperature    273.15
_cell_measurement_theta_max      66.464
_cell_measurement_theta_min      4.739
_cell_volume                     1834.8(5)
_computing_cell_refinement       'SAINT V8.40A (?, 2016)'
_computing_data_reduction        'SAINT V8.40A (?, 2016)'
_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      273.15
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0661
_diffrn_reflns_av_unetI/netI     0.0442
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            20508
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        66.876
_diffrn_reflns_theta_max         66.876
_diffrn_reflns_theta_min         4.739
_exptl_absorpt_coefficient_mu    1.936
_exptl_absorpt_correction_T_max  0.722
_exptl_absorpt_correction_T_min  0.511
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1507 before and 0.0949 after correction. The Ratio of minimum to maximum transmission is 0.7161. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            'clear brownish gray'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   brownish
_exptl_crystal_colour_primary    gray
_exptl_crystal_density_diffrn    1.306
_exptl_crystal_description       block
_exptl_crystal_F_000             752
_exptl_crystal_preparation       'pet ether in DCM'
_exptl_crystal_recrystallization_method 'slow evaporation'
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.238
_refine_diff_density_min         -0.360
_refine_diff_density_rms         0.043
_refine_ls_abs_structure_details
;
 Flack x determined using 1278 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.056(7)
_refine_ls_extinction_coef       0.0088(11)
_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   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         3219
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0351
_refine_ls_R_factor_gt           0.0334
_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^)+(0.0396P)^2^+0.5515P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0823
_refine_ls_wR_factor_ref         0.0850
_reflns_Friedel_coverage         0.741
_reflns_Friedel_fraction_full    0.988
_reflns_Friedel_fraction_max     0.987
_reflns_number_gt                3132
_reflns_number_total             3219
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1cc00793a2.cif
_cod_data_source_block           dm_3_78_0m
_cod_depositor_comments
'Adding full bibliography for 7128282--7128285.cif.'
_cod_database_code               7128282
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.722
_shelx_estimated_absorpt_t_min   0.511
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B)
2.b Aromatic/amide H refined with riding coordinates:
 N2(H2), C10(H10), C5(H5), C22(H22), C4(H4), C21(H21), C16(H16), C2(H2A),
 C3(H3), C19(H19), C12(H12), C15(H15), C18(H18), C13(H13), C14(H14)
;
_shelx_res_checksum              65255
_olex2_submission_special_instructions 'No special instructions were received'