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_4027585
_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            'C20 H12 S2'
_chemical_formula_weight         316.42
_chemical_name_systematic
; 
 6-(thiophen-2-yl)benzo[b]naphtha[2,3-d]thiophene 
;
_space_group_IT_number           56
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ab 2ac'
_symmetry_space_group_name_H-M   'P c c n'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   11.7061(6)
_cell_length_b                   28.9651(12)
_cell_length_c                   8.9072(4)
_cell_measurement_temperature    293(2)
_cell_volume                     3020.1(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 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  0.0334
_diffrn_reflns_av_sigmaI/netI    0.0339
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       33
_diffrn_reflns_limit_k_min       -33
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            12730
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.41
_exptl_absorpt_coefficient_mu    0.345
_exptl_absorpt_correction_T_max  0.9342
_exptl_absorpt_correction_T_min  0.9036
_exptl_crystal_density_diffrn    1.392
_exptl_crystal_F_000             1312
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.190
_refine_diff_density_min         -0.205
_refine_diff_density_rms         0.036
_refine_ls_extinction_coef       0.0012(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         2663
_refine_ls_number_restraints     59
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0666
_refine_ls_R_factor_gt           0.0368
_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^)+(0.0505P)^2^+0.4117P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0877
_refine_ls_wR_factor_ref         0.1029
_reflns_number_gt                1858
_reflns_number_total             2663
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo301410w_si_004.cif
_cod_data_source_block           shelxl
_cod_database_code               4027585