Synthesis and characterization of β,β′-dimethylated dithieno[3,2-b:2′,3′-d]pyrroles and their corresponding regioregular conducting electropolymers
Förtsch, Sebastian; Mena-Osteritz, Elena; Bäuerle, Peter; Polymer Chemistry 12 (2021) 3332–3345; doi:10.1039/D1PY00479D

data_1562547
_publ_section_title
;
 Synthesis and characterization of \b,\b&#x2032;-dimethylated
 dithieno[3,2-b:2&#x2032;,3&#x2032;-d]pyrroles and their corresponding
 regioregular conducting electropolymers
;
_journal_issue                   22
_journal_name_full               'Polymer Chemistry'
_journal_page_first              3332
_journal_page_last               3345
_journal_paper_doi               10.1039/D1PY00479D
_journal_volume                  12
_journal_year                    2021
_chemical_formula_moiety         'C16 H13 N S2'
_chemical_formula_sum            'C16 H13 N S2'
_chemical_formula_weight         283.39
_chemical_name_systematic        'Dimethyl Dithienopyrrol'
_space_group_crystal_system      orthorhombic
_space_group_IT_number           62
_space_group_name_Hall           '-P 2ac 2n'
_space_group_name_H-M_alt        'P n m a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2021-03-16
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-03-16 deposited with the CCDC.	2021-05-12 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.1113(3)
_cell_length_b                   14.1996(3)
_cell_length_c                   6.88839(13)
_cell_measurement_reflns_used    4460
_cell_measurement_temperature    149.95(10)
_cell_measurement_theta_max      73.7890
_cell_measurement_theta_min      6.2140
_cell_volume                     1380.26(5)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      149.95(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3385
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -45.00  20.00   1.00    1.00    --  -42.93  38.00 -90.00   65
  2  \w    -71.00  30.00   1.00    1.00    --  -42.93  57.00 150.00  101
  3  \w   -110.00 -71.00   1.00    1.00    --  -42.93 156.00 164.50   39
  4  \w     54.00  91.00   1.00    1.00    --  107.13  15.00-120.00   37
  5  \w     95.00 177.00   1.00    1.00    --  107.13  15.00-120.00   82
  6  \w    110.00 167.00   1.00    1.00    --  107.13 125.00-180.00   57
  7  \w     81.00 178.00   1.00    1.00    --  107.13  61.00 -90.00   97
  8  \w    148.00 174.00   1.00    1.00    --  107.13 125.00  30.00   26
  9  \w    122.00 148.00   1.00    1.00    --  107.13  61.00 120.00   26
 10  \w     98.00 125.00   1.00    1.00    --  107.13 125.00  30.00   27
 11  \w     88.00 147.00   1.00    1.00    --  107.13  45.00   0.00   59
 12  \w     49.00 126.00   1.00    1.00    --  107.13 -61.00 150.00   77
 13  \w     34.00 113.00   1.00    1.00    --  107.13-125.00  60.00   79
 14  \w     34.00 114.00   1.00    1.00    --  107.13-125.00   0.00   80
 15  \w     30.00  55.00   1.00    1.00    --  107.13 -95.00-180.00   25
 16  \w     78.00 104.00   1.00    1.00    --  107.13 -95.00-180.00   26
 17  \w     25.00 102.00   1.00    1.00    --  107.13 -95.00 120.00   77
 18  \w   -108.00 -24.00   1.00    1.00    --  -42.93 -57.00   0.00   84
 19  \w   -124.00 -94.00   1.00    1.00    --  -42.93 -99.00 150.00   30
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1055852000
_diffrn_orient_matrix_UB_12      -0.0125210000
_diffrn_orient_matrix_UB_13      -0.0513817000
_diffrn_orient_matrix_UB_21      0.0252186000
_diffrn_orient_matrix_UB_22      -0.0010060000
_diffrn_orient_matrix_UB_23      0.2177204000
_diffrn_orient_matrix_UB_31      -0.0124993000
_diffrn_orient_matrix_UB_32      -0.1076205000
_diffrn_orient_matrix_UB_33      0.0038659000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0330
_diffrn_reflns_av_unetI/netI     0.0169
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            9016
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.038
_diffrn_reflns_theta_min         6.234
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    3.350
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.78842
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.364
_exptl_crystal_description       prism
_exptl_crystal_F_000             592
_exptl_crystal_preparation       'n-Hexane solution'
_exptl_crystal_size_max          0.256
_exptl_crystal_size_mid          0.162
_exptl_crystal_size_min          0.099
_refine_diff_density_max         0.276
_refine_diff_density_min         -0.193
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       0.0006(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     99
_refine_ls_number_reflns         1462
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.087
_refine_ls_R_factor_all          0.0354
_refine_ls_R_factor_gt           0.0307
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0452P)^2^+0.5545P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0860
_refine_ls_wR_factor_ref         0.0898
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1299
_reflns_number_total             1462
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1py00479d2.cif
_cod_data_source_block           fos17015
_cod_depositor_comments          'Adding full bibliography for 1562547.cif.'
_cod_original_cell_volume        1380.26(4)
_cod_database_code               1562547
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         'C16 H13 N S2'
_reflns_odcompleteness_completeness 99.93
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C8(H8), C9(H9), C10(H10), C11(H11)
2.b Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C)
;
_olex2_date_sample_data_collection 2017-05-16
_olex2_submission_original_sample_id Me-DTP
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.365
_oxdiff_exptl_absorpt_empirical_full_min 0.633