N-acyldithieno[3,2-b:2',3'-d]pyrroles: second generation dithieno[3,2-b:2',3'-d]pyrrole building blocks with stabilized energy levels.
Evenson, Sean J.; Rasmussen, Seth C.; Organic letters 12 (2010) 4054–4057; doi:10.1021/ol101647f

data_1503175
_publ_section_title
;
 N-acyldithieno[3,2-b:2',3'-d]pyrroles: second generation
 dithieno[3,2-b:2',3'-d]pyrrole building blocks with stabilized energy
 levels.
;
_journal_issue                   18
_journal_name_full               'Organic letters'
_journal_page_first              4054
_journal_page_last               4057
_journal_paper_doi               10.1021/ol101647f
_journal_volume                  12
_journal_year                    2010
_chemical_formula_moiety         'C16 H19 N O S2'
_chemical_formula_sum            'C16 H19 N O S2'
_chemical_formula_weight         305.44
_chemical_name_common            N-Octanoyldithieno[3,2-b:2',3'-d]pyrrole
_chemical_name_systematic
; 
N-Octanoyldithieno[3,2-b:2',3'-d]pyrrole
;
_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
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.891(8)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.070(3)
_cell_length_b                   10.917(5)
_cell_length_c                   17.772(8)
_cell_measurement_reflns_used    1785
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      26.97
_cell_measurement_theta_min      2.29
_cell_volume                     1565.5(12)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_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      273(2)
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_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  0.0452
_diffrn_reflns_av_sigmaI/netI    0.0498
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            10004
_diffrn_reflns_theta_full        28.03
_diffrn_reflns_theta_max         28.03
_diffrn_reflns_theta_min         2.19
_exptl_absorpt_coefficient_mu    0.335
_exptl_absorpt_correction_T_max  1.000000
_exptl_absorpt_correction_T_min  0.548578
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            clear-yel
_exptl_crystal_density_diffrn    1.296
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod/plate
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.80
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.231
_refine_diff_density_min         -0.254
_refine_diff_density_rms         0.061
_refine_ls_extinction_coef       0.015(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   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         3747
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0733
_refine_ls_R_factor_gt           0.0430
_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^)+(0.0613P)^2^+0.2064P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1134
_refine_ls_wR_factor_ref         0.1325
_reflns_number_gt                2433
_reflns_number_total             3747
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol101647f_si_002.cif
_cod_data_source_block           sxe1m
_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 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        1565.6(12)
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               1503175