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_4033307
_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         'C27 H38 N3 S2 Si'
_chemical_formula_sum            'C27 H38 N3 S2 Si'
_chemical_formula_weight         496.81
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2016-03-03
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_cell_angle_alpha                90
_cell_angle_beta                 96.505(3)
_cell_angle_gamma                90
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_cell_length_a                   14.8601(4)
_cell_length_b                   17.8661(5)
_cell_length_c                   9.9880(4)
_cell_measurement_reflns_used    3139
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      66.305
_cell_measurement_theta_min      5.654
_cell_volume                     2634.66(15)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.0
_diffrn_measured_fraction_theta_full 0.967
_diffrn_measured_fraction_theta_max 0.967
_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  0.0936
_diffrn_reflns_av_unetI/netI     0.0695
_diffrn_reflns_Laue_measured_fraction_full 0.967
_diffrn_reflns_Laue_measured_fraction_max 0.967
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            16757
_diffrn_reflns_point_group_measured_fraction_full 0.967
_diffrn_reflns_point_group_measured_fraction_max 0.967
_diffrn_reflns_theta_full        66.724
_diffrn_reflns_theta_max         66.724
_diffrn_reflns_theta_min         5.653
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.411
_exptl_absorpt_correction_T_max  0.5842
_exptl_absorpt_correction_T_min  0.4869
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/2 (Bruker,2014/2) was used for absorption correction.
wR2(int) was 0.0960 before and 0.0600 after correction.
The Ratio of minimum to maximum transmission is 0.8334.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.252
_exptl_crystal_description       needle
_exptl_crystal_F_000             1068
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.048
_exptl_crystal_size_min          0.037
_refine_diff_density_max         0.633
_refine_diff_density_min         -0.349
_refine_diff_density_rms         0.067
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     305
_refine_ls_number_reflns         4509
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0854
_refine_ls_R_factor_gt           0.0514
_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^)+(0.0627P)^2^+1.3464P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1234
_refine_ls_wR_factor_ref         0.1391
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3113
_reflns_number_total             4509
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo7b02570_si_002.cif
_cod_data_source_block           6
_cod_depositor_comments
'Adding full bibliography for 4033305--4033307.cif.'
_cod_database_code               4033307
_shelx_estimated_absorpt_t_max   0.916
_shelx_estimated_absorpt_t_min   0.607
_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 Ternary CH refined with riding coordinates:
 C19(H19), C22(H22), C25(H25)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B), C5(H5A,H5B), C6(H6A,H6B)
2.c Aromatic/amide H refined with riding coordinates:
 C8(H8), C9(H9), C14(H14), C15(H15)
2.d Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C20(H20A,H20B,H20C), C21(H21A,H21B,H21C), C23(H23A,H23B,
 H23C), C24(H24A,H24B,H24C), C26(H26A,H26B,H26C), C27(H27A,H27B,H27C)
;
_shelx_res_checksum              79067
_shelx_hkl_checksum              53912
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'