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_4027584
_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            'C21 H15 S2'
_chemical_formula_weight         331.45
_chemical_name_systematic
;
2-(thiophene-2-yl)-4-p-tolylnaphtho[2,3-b]thiophene
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.000(5)
_cell_angle_beta                 93.784(5)
_cell_angle_gamma                90.000(5)
_cell_formula_units_Z            4
_cell_length_a                   8.852(5)
_cell_length_b                   7.722(5)
_cell_length_c                   26.705(5)
_cell_measurement_temperature    293(2)
_cell_volume                     1821.4(16)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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  0.0569
_diffrn_reflns_av_sigmaI/netI    0.0460
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            14111
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.53
_exptl_absorpt_coefficient_mu    0.289
_exptl_absorpt_correction_T_max  0.9445
_exptl_absorpt_correction_T_min  0.9184
_exptl_crystal_density_diffrn    1.209
_exptl_crystal_F_000             692
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.204
_refine_diff_density_min         -0.197
_refine_diff_density_rms         0.034
_refine_ls_extinction_coef       0.0124(13)
_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   1.009
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     241
_refine_ls_number_reflns         3195
_refine_ls_number_restraints     9
_refine_ls_restrained_S_all      1.019
_refine_ls_R_factor_all          0.0692
_refine_ls_R_factor_gt           0.0388
_refine_ls_shift/su_max          0.031
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0450P)^2^+0.4246P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0921
_refine_ls_wR_factor_ref         0.1103
_reflns_number_gt                2162
_reflns_number_total             3195
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo301410w_si_003.cif
_cod_data_source_block           final
_cod_database_code               4027584