Synthetic Utility of Arylmethylsulfones: Annulative π-Extension of Aromatics and Hetero-aromatics Involving Pd(0)-Catalyzed Heck Coupling Reactions.
Sankar, Elumalai; Raju, Potharaju; Karunakaran, Jayachandran; Mohanakrishnan, Arasambattu K.; The Journal of organic chemistry 82 (2017) 13583–13593; doi:10.1021/acs.joc.7b01813

data_4033234
_publ_section_title
;
 Synthetic Utility of Arylmethylsulfones: Annulative \p-Extension of
 Aromatics and Hetero-aromatics Involving Pd(0)-Catalyzed Heck Coupling
 Reactions.
;
_journal_issue                   24
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              13583
_journal_page_last               13593
_journal_paper_doi               10.1021/acs.joc.7b01813
_journal_volume                  82
_journal_year                    2017
_chemical_formula_sum            'C24 H19 Br N2 O9 S3'
_chemical_formula_weight         655.00
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                66.9180(10)
_cell_angle_beta                 68.2530(10)
_cell_angle_gamma                71.672(2)
_cell_formula_units_Z            4
_cell_length_a                   14.6299(4)
_cell_length_b                   14.6404(4)
_cell_length_c                   15.5052(4)
_cell_measurement_reflns_used    15536
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.3
_cell_measurement_theta_min      1.3
_cell_volume                     2781.53(13)
_computing_cell_refinement       'APEX2/SAINT (Bruker , 2004)'
_computing_data_collection       'APEX2 (Bruker , 2004)'
_computing_data_reduction        'SAINT/XPREP (Bruker , 2004)'
_computing_molecular_graphics    'ORTEP3 (Farrugia, 2012)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Bruker axs kappa apex2 CCD diffractometer'
_diffrn_measurement_method       '\w and \ f scan'
_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  0.0607
_diffrn_reflns_av_sigmaI/netI    0.0702
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            76995
_diffrn_reflns_theta_full        29.64
_diffrn_reflns_theta_max         29.64
_diffrn_reflns_theta_min         1.49
_exptl_absorpt_coefficient_mu    1.757
_exptl_absorpt_correction_T_max  0.7202
_exptl_absorpt_correction_T_min  0.7202
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.564
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1326
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.761
_refine_diff_density_min         -0.539
_refine_diff_density_rms         0.077
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.983
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     703
_refine_ls_number_reflns         15536
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.983
_refine_ls_R_factor_all          0.1671
_refine_ls_R_factor_gt           0.0491
_refine_ls_shift/su_max          8.457
_refine_ls_shift/su_mean         0.613
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0801P)^2^+0.7534P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1240
_refine_ls_wR_factor_ref         0.1911
_reflns_number_gt                5186
_reflns_number_total             15536
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo7b01813_si_002.cif
_cod_data_source_block           final
_cod_depositor_comments
;
Adding full bibliography for 4033233--4033234.cif.

2020-06-08
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C48 H37 Br2 N4 O18 S6'
_cod_original_formula_weight         1310.00
_cod_original_formula_units_Z            2
_cod_original_sg_symbol_H-M      p-1
_cod_database_code               4033234