Synthesis of nitrogen-bridged terthiophenes by tandem buchwald-hartwig coupling and their properties.
Mitsudo, Koichi; Shimohara, Shuichi; Mizoguchi, Jun; Mandai, Hiroki; Suga, Seiji; Organic letters 14 (2012) 2702–2705; doi:10.1021/ol300887t

data_1507706
_publ_section_title
;
 Synthesis of nitrogen-bridged terthiophenes by tandem buchwald-hartwig
 coupling and their properties.
;
_journal_issue                   11
_journal_name_full               'Organic letters'
_journal_page_first              2702
_journal_page_last               2705
_journal_paper_doi               10.1021/ol300887t
_journal_volume                  14
_journal_year                    2012
_chemical_formula_moiety         'C20 H22 N2 S3'
_chemical_formula_sum            'C20 H22 N2 S3'
_chemical_formula_weight         386.58
_chemical_name_systematic
;
 N,N'-Dibutyl-trithienodipyrrole
;
_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
_cell_angle_alpha                90.00
_cell_angle_beta                 110.20(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.242(18)
_cell_length_b                   13.432(19)
_cell_length_c                   13.31(2)
_cell_measurement_reflns_used    4535
_cell_measurement_temperature    93.1500
_cell_measurement_theta_max      27.4198
_cell_measurement_theta_min      3.0333
_cell_volume                     1886(5)
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2008)'
_computing_molecular_graphics    'Yadokari-XG 2009 (Wakita Nemoto et al., 2009)'
_computing_publication_material  'Yadokari-XG 2009 (Wakita,Nemoto et al., 2009)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR2004 (Burla, et al., 2005)'
_diffrn_ambient_temperature      93.1500
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Rigaku Saturn724'
_diffrn_measurement_method       dtprofit.ref
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_source         'Rotating Anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.1046
_diffrn_reflns_av_sigmaI/netI    0.0922
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            20835
_diffrn_reflns_theta_full        27.49
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         3.03
_exptl_absorpt_coefficient_mu    0.398
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.6951
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.361
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Platelet
_exptl_crystal_F_000             816
_exptl_crystal_size_max          0.2980
_exptl_crystal_size_mid          0.2840
_exptl_crystal_size_min          0.0200
_refine_diff_density_max         1.685
_refine_diff_density_min         -0.687
_refine_diff_density_rms         0.141
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         4286
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.1370
_refine_ls_R_factor_gt           0.0937
_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^)+(0.1626P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2318
_refine_ls_wR_factor_ref         0.2749
_reflns_number_gt                2580
_reflns_number_total             4286
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol300887t_si_001.cif
_cod_data_source_block           2f
_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 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        1887(5)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               1507706