Pd-catalyzed Heck-conjoined amidation and concomitant chemoselective Michael-addition: an efficient tandem approach to highly functionalized tetrahydroquinazolines from o-haloanilines.
Saunthwal, Rakesh K.; Patel, Monika; Danodia, Abhinandan K.; Verma, Akhilesh K.; Organic & biomolecular chemistry 13 (2015) 1521–1530; doi:10.1039/c4ob02286f

data_7154219
_publ_section_title
;
 Pd-catalyzed Heck-conjoined amidation and concomitant chemoselective
 Michael-addition: an efficient tandem approach to highly functionalized
 tetrahydroquinazolines from o-haloanilines.
;
_journal_issue                   5
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              1521
_journal_page_last               1530
_journal_paper_doi               10.1039/c4ob02286f
_journal_volume                  13
_journal_year                    2015
_chemical_formula_moiety         'C17 H16 N2 O2 S'
_chemical_formula_sum            'C17 H16 N2 O2 S'
_chemical_formula_weight         312.38
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2014-06-02 deposited with the CCDC.
2014-11-26 downloaded from the CCDC.
;
_cell_angle_alpha                90.000(5)
_cell_angle_beta                 92.408(5)
_cell_angle_gamma                90.000(5)
_cell_formula_units_Z            8
_cell_length_a                   9.751(5)
_cell_length_b                   18.905(5)
_cell_length_c                   16.646(5)
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.00
_cell_measurement_theta_min      2.20
_cell_volume                     3066(2)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Xcalibur Sapphire3'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0456
_diffrn_reflns_av_sigmaI/netI    0.0424
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            20532
_diffrn_reflns_theta_full        24.99
_diffrn_reflns_theta_max         24.99
_diffrn_reflns_theta_min         2.15
_exptl_absorpt_coefficient_mu    0.220
_exptl_absorpt_correction_T_max  0.9574
_exptl_absorpt_correction_T_min  0.9471
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_density_diffrn    1.354
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1312
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.376
_refine_diff_density_min         -0.266
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     413
_refine_ls_number_reflns         5414
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0602
_refine_ls_R_factor_gt           0.0418
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0454P)^2^+1.6092P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0958
_refine_ls_wR_factor_ref         0.1018
_reflns_number_gt                4259
_reflns_number_total             5414
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4ob02286f3.cif
_cod_data_source_block           shelxl
_cod_depositor_comments          'Adding full bibliography for 7154219.cif.'
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7154219