A Simple and Efficient Route to N-Functionalized Dithieno[3,2-b:2',3'-d]pyrroles: Fused-Ring Building Blocks for New Conjugated Polymeric Systems
Katsu Ogawa; Seth C. Rasmussen; Journal of Organic Chemistry 68 (2003) 2921–2928; doi:10.1021/jo034078k

data_4022403
_publ_section_title
;
 A Simple and Efficient Route to N-Functionalized
 Dithieno[3,2-b:2',3'-d]pyrroles: Fused-Ring Building Blocks
 for New Conjugated Polymeric Systems
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              2921
_journal_page_last               2928
_journal_paper_doi               10.1021/jo034078k
_journal_volume                  68
_journal_year                    2003
_chemical_formula_sum            'C20 H21 N S2'
_chemical_formula_weight         339.50
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 96.465(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   12.9396(12)
_cell_length_b                   7.9145(7)
_cell_length_c                   35.458(3)
_cell_measurement_temperature    298(2)
_cell_volume                     3608.2(6)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.928
_diffrn_measured_fraction_theta_max 0.928
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_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  0.0431
_diffrn_reflns_av_sigmaI/netI    0.0899
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       45
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            21744
_diffrn_reflns_theta_full        28.28
_diffrn_reflns_theta_max         28.28
_diffrn_reflns_theta_min         1.62
_exptl_absorpt_coefficient_mu    0.294
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            'clr colorle'
_exptl_crystal_density_diffrn    1.250
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1440
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.44
_refine_diff_density_max         0.210
_refine_diff_density_min         -0.208
_refine_diff_density_rms         0.033
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.805
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     415
_refine_ls_number_reflns         8317
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.805
_refine_ls_R_factor_all          0.1612
_refine_ls_R_factor_gt           0.0453
_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^)+(0.0627P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1048
_refine_ls_wR_factor_ref         0.1313
_reflns_number_gt                2971
_reflns_number_total             8317
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo034078ksi20030122_033401_2.cif
_cod_data_source_block           PhDTP
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4022403