Pyrrolo[2,3-d:5,4-d']bisthiazoles: Alternate Synthetic Routes and a Comparative Study to Analogous Fused-Ring Bithiophenes.
Uzelac, Eric J.; McCausland, Casey B.; Rasmussen, Seth C.; The Journal of organic chemistry 83 (2018) 664–671; doi:10.1021/acs.joc.7b02570

data_4033306
_publ_section_title
;
 Pyrrolo[2,3-d:5,4-d']bisthiazoles: Alternate Synthetic Routes and a
 Comparative Study to Analogous Fused-Ring Bithiophenes.
;
_journal_issue                   2
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              664
_journal_page_last               671
_journal_paper_doi               10.1021/acs.joc.7b02570
_journal_volume                  83
_journal_year                    2018
_chemical_formula_moiety         'C12 H15 N3 S2'
_chemical_formula_sum            'C12 H15 N3 S2'
_chemical_formula_weight         265.39
_chemical_melting_point          82.5
_chemical_name_common
;
4-t-butyl-PBTz
;
_chemical_name_systematic
;
4-Hexyl-4H-pyrrolo[2,3-d:5,4-d']bisthiazole
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_Hall           'C -2yc'
_space_group_name_H-M_alt        'C 1 c 1'
_symmetry_space_group_name_Hall  'C -2yc'
_symmetry_space_group_name_H-M   'C 1 c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2017-10-04
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_cell_angle_alpha                90
_cell_angle_beta                 107.618(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.4255(9)
_cell_length_b                   11.8733(7)
_cell_length_c                   9.8260(7)
_cell_measurement_reflns_used    2425
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      65.144
_cell_measurement_theta_min      5.51
_cell_volume                     1270.46(16)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0
_diffrn_reflns_av_unetI/netI     0.0567
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            1131
_diffrn_reflns_point_group_measured_fraction_full 0.498
_diffrn_reflns_point_group_measured_fraction_max 0.498
_diffrn_reflns_theta_full        67.044
_diffrn_reflns_theta_max         67.044
_diffrn_reflns_theta_min         5.512
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.636
_exptl_absorpt_correction_T_max  0.752818
_exptl_absorpt_correction_T_min  0.619384
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 TWINABS-2012/1 (Bruker,2012) was used for absorption correction.

For component 1:
 wR2(int) was 0.0980 before and 0.0725 after correction.
 The Ratio of minimum to maximum transmission not present.
 The \l/2 correction factor is Not present

For component 2:
 wR2(int) was 0.1363 before and 0.0764 after correction.
 The Ratio of minimum to maximum transmission is 0.80.
 The \l/2 correction factor is Not present

Final HKLF 4 output contains 22632 reflections, Rint = 0.1790
 (4564 with I > 3sig(I), Rint = 0.0972)
;
_exptl_crystal_colour            'clear dark yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.387
_exptl_crystal_description       needle
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.391
_refine_diff_density_min         -0.395
_refine_diff_density_rms         0.094
_refine_ls_abs_structure_details
;
No quotients, so Flack parameter determined by classical intensity fit
;
_refine_ls_abs_structure_Flack   0.09(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.121
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         1131
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.120
_refine_ls_R_factor_all          0.0616
_refine_ls_R_factor_gt           0.0531
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0849P)^2^+0.9958P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1368
_refine_ls_wR_factor_ref         0.1422
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    0.000
_reflns_Friedel_fraction_max     0.000
_reflns_number_gt                996
_reflns_number_total             1131
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo7b02570_si_002.cif
_cod_data_source_block           5a
_cod_depositor_comments
'Adding full bibliography for 4033305--4033307.cif.'
_cod_database_code               4033306
_shelx_shelxl_version_number     2016/4
_shelx_estimated_absorpt_t_max   0.822
_shelx_estimated_absorpt_t_min   0.691
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C008(H00A,H00B), C00C(H00C,H00D), C00D(H00E,H00F), C00F(H00H,H00I), C00G(H00J,
 H00K)
2.b Aromatic/amide H refined with riding coordinates:
 C009(H009), C00E(H00G)
2.c Idealised Me refined as rotating group:
 C00H(H00L,H00M,H00N)
;
_olex2_submission_special_instructions 'No special instructions were received'