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_1507707
_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         'C14 H10 N2 S3'
_chemical_formula_sum            'C14 H10 N2 S3'
_chemical_formula_weight         302.42
_chemical_name_common            N,N'-dimethyl-bis(dithienopyrrolo)thiophene
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yab'
_symmetry_space_group_name_H-M   'P 1 21/a 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                 97.754(8)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.427(5)
_cell_length_b                   14.544(10)
_cell_length_c                   12.017(8)
_cell_measurement_reflns_used    2742
_cell_measurement_temperature    100.1500
_cell_measurement_theta_max      27.5049
_cell_measurement_theta_min      3.0516
_cell_volume                     1286.2(15)
_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      100.1500
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.981
_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  0.1933
_diffrn_reflns_av_sigmaI/netI    0.2510
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            14476
_diffrn_reflns_theta_full        27.49
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         3.10
_exptl_absorpt_coefficient_mu    0.561
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.6760
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.562
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Needle
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.5600
_exptl_crystal_size_mid          0.0500
_exptl_crystal_size_min          0.0300
_refine_diff_density_max         1.953
_refine_diff_density_min         -0.720
_refine_diff_density_rms         0.186
_refine_ls_extinction_coef       0.005(2)
_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   1.088
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     175
_refine_ls_number_reflns         2897
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.088
_refine_ls_R_factor_all          0.1605
_refine_ls_R_factor_gt           0.1301
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1010P)^2^+4.1597P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3011
_refine_ls_wR_factor_ref         0.3179
_reflns_number_gt                1856
_reflns_number_total             2897
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol300887t_si_001.cif
_cod_data_source_block           2g
_cod_depositor_comments
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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_sg_symbol_H-M      'P 21/a'
_cod_database_code               1507707