Synthesis of Annulated Arenes and Heteroarenes Involving Lewis Acid-Mediated Regioselective Annulation of Unsymmetrical 1,2-(Diaryl/diheteroarylmethine)dipivalates
Ramakrishnan Sivasakthikumaran; Meganathan Nandakumar; Arasambattu K. Mohanakrishnan; Journal of Organic Chemistry 77 (2012) 9053–9071; doi:10.1021/jo301410w

data_4027586
_publ_section_title
;
 Synthesis of Annulated Arenes and Heteroarenes Involving Lewis
 Acid-Mediated Regioselective Annulation of Unsymmetrical
 1,2-(Diaryl/diheteroarylmethine)dipivalates
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              9053
_journal_page_last               9071
_journal_paper_doi               10.1021/jo301410w
_journal_volume                  77
_journal_year                    2012
_chemical_formula_sum            'C26 H16 S'
_chemical_formula_weight         360.45
_chemical_name_systematic
; 
 7-phenylanthra[2,3-d]benzo[b]thiophene 
;
_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                105.619(4)
_cell_angle_beta                 95.630(4)
_cell_angle_gamma                111.055(4)
_cell_formula_units_Z            2
_cell_length_a                   9.0328(6)
_cell_length_b                   10.9285(8)
_cell_length_c                   11.0232(8)
_cell_measurement_temperature    293(2)
_cell_volume                     954.75(12)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.0274
_diffrn_reflns_av_sigmaI/netI    0.0206
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            14211
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.97
_exptl_absorpt_coefficient_mu    0.176
_exptl_absorpt_correction_T_max  0.9656
_exptl_absorpt_correction_T_min  0.9490
_exptl_crystal_density_diffrn    1.254
_exptl_crystal_F_000             376
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         1.710
_refine_diff_density_min         -0.310
_refine_diff_density_rms         0.105
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.747
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     263
_refine_ls_number_reflns         3351
_refine_ls_number_restraints     86
_refine_ls_restrained_S_all      1.774
_refine_ls_R_factor_all          0.1190
_refine_ls_R_factor_gt           0.1067
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.2000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3673
_refine_ls_wR_factor_ref         0.3877
_reflns_number_gt                2696
_reflns_number_total             3351
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo301410w_si_005.cif
_cod_data_source_block           shelxl
_cod_database_code               4027586