A direct synthesis of selenophenes by cu-catalyzed one-pot addition of a selenium moiety to (e,e)-1,3-dienyl bromides and subsequent nucleophilic cyclization.
Maity, Pintu; Kundu, Debasish; Roy, Rajdip; Ranu, Brindaban C.; Organic letters 16 (2014) 4122–4125; doi:10.1021/ol501820e

data_1517222
_publ_section_title
;
 A direct synthesis of selenophenes by cu-catalyzed one-pot addition of a
 selenium moiety to (e,e)-1,3-dienyl bromides and subsequent nucleophilic
 cyclization.
;
_journal_issue                   16
_journal_name_full               'Organic letters'
_journal_page_first              4122
_journal_page_last               4125
_journal_paper_doi               10.1021/ol501820e
_journal_volume                  16
_journal_year                    2014
_chemical_formula_moiety         'C16 H10 O2 Se3'
_chemical_formula_sum            'C16 H10 O2 Se3'
_chemical_formula_weight         471.12
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_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                90.00
_cell_angle_beta                 96.147(8)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   17.967(5)
_cell_length_b                   6.0336(16)
_cell_length_c                   14.479(4)
_cell_measurement_temperature    296(2)
_cell_volume                     1560.6(7)
_computing_cell_refinement       'Bruker Apex II'
_computing_data_collection       'Bruker Apex II'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'Mercury 2.3'
_computing_publication_material  'Shelxl 97'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Bruker Apex II'
_diffrn_measurement_method       'Omega 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  0.0519
_diffrn_reflns_av_sigmaI/netI    0.0511
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            16193
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         2.28
_exptl_absorpt_coefficient_mu    7.071
_exptl_absorpt_correction_T_max  0.195
_exptl_absorpt_correction_T_min  0.088
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            YELLOW
_exptl_crystal_density_diffrn    2.005
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       FIBRE
_exptl_crystal_F_000             896
_exptl_crystal_size_max          0.54
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.497
_refine_diff_density_min         -0.547
_refine_diff_density_rms         0.143
_refine_ls_extinction_method     none
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_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         3546
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.016
_refine_ls_R_factor_all          0.0747
_refine_ls_R_factor_gt           0.0404
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0815P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1094
_refine_ls_wR_factor_ref         0.1369
_reflns_number_gt                2360
_reflns_number_total             3546
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol501820e_si_002.cif
_cod_data_source_block           pm
_cod_depositor_comments          'Adding full bibliography for 1517222.cif.'
_cod_original_cell_volume        1560.5(7)
_cod_database_code               1517222