One-pot synthesis of benzo[b]thiophenes and benzo[b]selenophenes from o-halo-substituted ethynylbenzenes: convenient approach to mono-, bis-, and tris-chalcogenophene-annulated benzenes.
Kashiki, Tomoya; Shinamura, Shoji; Kohara, Masahiro; Miyazaki, Eigo; Takimiya, Kazuo; Ikeda, Masaaki; Kuwabara, Hirokazu; Organic letters 11 (2009) 2473–2475; doi:10.1021/ol900809w

data_1503960
_publ_section_title
;
 One-pot synthesis of benzo[b]thiophenes and benzo[b]selenophenes from
 o-halo-substituted ethynylbenzenes: convenient approach to mono-, bis-,
 and tris-chalcogenophene-annulated benzenes.
;
_journal_issue                   11
_journal_name_full               'Organic letters'
_journal_page_first              2473
_journal_page_last               2475
_journal_paper_doi               10.1021/ol900809w
_journal_volume                  11
_journal_year                    2009
_chemical_formula_moiety         'C12 H6 Se3'
_chemical_formula_sum            'C12 H6 Se3'
_chemical_formula_weight         387.05
_chemical_name_common            BTS
_chemical_name_systematic
; 
BTS 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_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(2)
_cell_angle_beta                 112.694(3)
_cell_angle_gamma                90.000(2)
_cell_formula_units_Z            4
_cell_length_a                   9.079(8)
_cell_length_b                   11.625(9)
_cell_length_c                   11.712(10)
_cell_measurement_reflns_used    2576
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.4835
_cell_measurement_theta_min      2.9999
_cell_volume                     1140.4(17)
_computing_cell_refinement       CRYSTALCLEAR
_computing_data_collection       CRYSTALCLEAR
_computing_data_reduction        'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 14.7059
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Rigaku/MSC Mercury CCD'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71070
_diffrn_reflns_av_R_equivalents  0.0507
_diffrn_reflns_av_sigmaI/netI    0.0581
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            8444
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.00
_diffrn_standards_number         8693
_exptl_absorpt_coefficient_mu    9.635
_exptl_absorpt_correction_T_max  0.2488
_exptl_absorpt_correction_T_min  0.1602
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    2.254
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.469
_refine_diff_density_min         -1.009
_refine_diff_density_rms         0.135
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.953
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2587
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.953
_refine_ls_R_factor_all          0.0793
_refine_ls_R_factor_gt           0.0571
_refine_ls_shift/su_max          0.017
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1576
_refine_ls_wR_factor_ref         0.1706
_reflns_number_gt                1571
_reflns_number_total             2587
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol900809w_si_002.cif
_cod_data_source_block           BTS
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_absorpt_correction_type' value 'Multi-scan' changed to
'multi-scan' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        1140.5(16)
_cod_database_code               1503960