4-Amino-2,1,3-benzothiadiazole as a Removable Bidentate Directing Group for the Pd(II)-Catalyzed Arylation/Oxygenation of sp<sup>2</sup>/sp<sup>3</sup> β-C-H Bonds of Carboxamides.
Reddy, Chennakesava; Bisht, Narendra; Parella, Ramarao; Babu, Srinivasarao Arulananda; The Journal of organic chemistry 81 (2016) 12143–12168; doi:10.1021/acs.joc.6b01831

data_4037238
_publ_section_title
;
 4-Amino-2,1,3-benzothiadiazole as a Removable Bidentate Directing Group
 for the Pd(II)-Catalyzed Arylation/Oxygenation of
 sp<sup>2</sup>/sp<sup>3</sup> \b-C-H Bonds of Carboxamides.
;
_journal_issue                   24
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              12143
_journal_page_last               12168
_journal_paper_doi               10.1021/acs.joc.6b01831
_journal_volume                  81
_journal_year                    2016
_chemical_formula_moiety         'C23 H17 Cl2 N3 O S'
_chemical_formula_sum            'C23 H17 Cl2 N3 O S'
_chemical_formula_weight         454.35
_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
_audit_creation_date             2015-12-04
_audit_creation_method
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_cell_angle_alpha                90
_cell_angle_beta                 97.907(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.933(5)
_cell_length_b                   19.878(8)
_cell_length_c                   9.767(4)
_cell_measurement_reflns_used    5703
_cell_measurement_temperature    296.0
_cell_measurement_theta_max      21.924
_cell_measurement_theta_min      2.34
_cell_volume                     2102.4(15)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_diffrn_ambient_temperature      296.0
_diffrn_measured_fraction_theta_full 0.968
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0571
_diffrn_reflns_av_unetI/netI     0.0355
_diffrn_reflns_Laue_measured_fraction_full 0.968
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            29467
_diffrn_reflns_point_group_measured_fraction_full 0.968
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.025
_diffrn_reflns_theta_min         1.880
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.429
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.6628
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.0811 before and 0.0657 after correction.
The Ratio of minimum to maximum transmission is 0.8891.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.435
_exptl_crystal_description       block
_exptl_crystal_F_000             936
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.733
_refine_diff_density_min         -0.345
_refine_diff_density_rms         0.101
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.098
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     272
_refine_ls_number_reflns         3687
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.098
_refine_ls_R_factor_all          0.1083
_refine_ls_R_factor_gt           0.0871
_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^)+(0.1796P)^2^+2.0565P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2740
_refine_ls_wR_factor_ref         0.2950
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2689
_reflns_number_total             3687
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo6b01831_si_002.cif
_cod_data_source_block           cr_1369a2
_cod_original_cell_volume        2102.6(15)
_cod_database_code               4037238
_shelxl_version_number           2013-4
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0(10) 1(10)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
3.a Ternary CH refined with riding coordinates:
 C5(H5), C3(H3), C2(H2)
3.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B)
3.c Aromatic/amide H refined with riding coordinates:
 N1(H1), C17(H17), C7(H7), C11(H11), C8(H8), C13(H13), C23(H23), C10(H10),
 C16(H16), C22(H22), C14(H14), C21(H21)
;
_olex2_submission_special_instructions 'No special instructions were received'