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_4033305
_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         'C28 H51 N3 S2 Si2'
_chemical_formula_sum            'C28 H51 N3 S2 Si2'
_chemical_formula_weight         550.01
_chemical_melting_point          82.4
_chemical_name_common            4-t-butylPBTz
_chemical_name_systematic
;
4-tert-butyl-2,6-bis(triisopropylsilyl)-4H-pyrrolo[2,3-d:5,4-d']bisthiazole
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_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
_audit_creation_date             2016-02-23
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_cell_angle_alpha                90
_cell_angle_beta                 108.1750(10)
_cell_angle_gamma                90
_cell_formula_units_Z            16
_cell_length_a                   27.9822(5)
_cell_length_b                   15.7268(3)
_cell_length_c                   30.7786(6)
_cell_measurement_reflns_used    9832
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      66.521
_cell_measurement_theta_min      3.022
_cell_volume                     12869.0(4)
_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)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100.08
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_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  0.0516
_diffrn_reflns_av_unetI/netI     0.0407
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       33
_diffrn_reflns_limit_h_min       -33
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_number            90686
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        66.569
_diffrn_reflns_theta_max         66.569
_diffrn_reflns_theta_min         3.022
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.356
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_correction_T_min  0.6702
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0680 before and 0.0472 after correction.
The Ratio of minimum to maximum transmission is 0.8903.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.136
_exptl_crystal_description       plate
_exptl_crystal_F_000             4800
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.013
_refine_diff_density_max         0.935
_refine_diff_density_min         -0.357
_refine_diff_density_rms         0.060
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1321
_refine_ls_number_reflns         22551
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0624
_refine_ls_R_factor_gt           0.0472
_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^)+(0.0574P)^2^+9.0617P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1139
_refine_ls_wR_factor_ref         0.1214
_reflns_Friedel_coverage         0.000
_reflns_number_gt                18345
_reflns_number_total             22551
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo7b02570_si_002.cif
_cod_data_source_block           4d
_cod_depositor_comments
'Adding full bibliography for 4033305--4033307.cif.'
_cod_database_code               4033305
_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 Ternary CH refined with riding coordinates:
 C019(H019), C01B(H01B), C01G(H01G), C01H(H01H), C01J(H01M), C01N(H01N),
 C01O(H01O), C01P(H01P), C01S(H01S), C01W(H01W), C01Y(H01Y), C01Z(H01Z),
 C023(H023), C025(H025), C026(H026), C027(H027), C028(H028), C029(H029),
 C02A(H02G), C02B(H2CA), C02K(H02K), C02M(H02M), C034(H034), C037(H037)
2.b Idealised Me refined as rotating group:
 C01L(H01A,H01C,H01D), C01M(H01E,H01F,H01I), C01R(H01J,H01K,H01L), C020(H02A,
 H02B,H02C), C021(H02D,H02E,H02F), C022(H1CA,H,HA), C024(H02S,H02T,H02U),
 C02C(H9AA,HB,HC), C02D(H02V,H02W,H02X), C02E(H0BA,HD,HE), C02F(H02Y,HF,HG),
 C02G(H3CA,HH,HI), C02H(H02Z,HJ,HK), C02I(H4CA,HL,HM), C02J(H1BA,HN,HO),
 C02L(H5CA,HP,HQ), C02N(H2BA,HR,HS), C02O(H02H,H02I,H02J), C02P(H02L,H02N,H02O),
  C02Q(H6CA,HT,HU), C02R(H02,HV,HW), C02S(H3BA,HX,HY), C02T(H4BA,HZ,H7DA),
 C02U(H5BA,H8DA,H9DA), C02V(H7CA,H0EA,H1EA), C02W(H0AA,H2EA,H3EA), C02X(H02P,
 H02Q,H02R), C02Y(H1AA,H4EA,H5EA), C02Z(H2AA,H6EA,H7EA), C030(H6BA,H8EA,H9EA),
 C031(H03A,H03B,H03C), C032(H03,H0FA,H1FA), C033(H03D,H03E,H03F), C035(H8CA,
 H2FA,H3FA), C036(H03G,H03H,H03I), C038(H3AA,H4FA,H5FA), C039(H9CA,H6FA,H7FA),
 C03A(H03J,H03K,H03L), C03B(H7BA,H8FA,H9FA), C03C(H03M,H03N,H03O), C03D(H0DA,
 H0GA,H1GA), C03E(H03P,H03Q,H03R), C03F(H03S,H03T,H03U), C03G(H03V,H03W,H03X),
 C03H(H03Y,H2GA,H3GA), C03I(H8BA,H4GA,H5GA), C03J(H9BA,H6GA,H7GA), C03K(H1DA,
 H8GA,H9GA), C03L(H4AA,H0HA,H1HA), C03M(H5AA,H2HA,H3HA), C03N(H6AA,H4HA,H5HA),
 C03O(H7AA,H6HA,H7HA), C03P(H8AA,H8HA,H9HA), C03Q(H03Z,H0IA,H1IA), C03R(H0CA,
 H2IA,H3IA), C03S(H2DA,H4IA,H5IA), C03T(H3DA,H6IA,H7IA), C03U(H4DA,H8IA,H9IA),
 C03V(H5DA,H0JA,H1JA), C03W(H6DA,H2JA,H3JA)
;
_shelx_res_checksum              36942
_shelx_hkl_checksum              93524
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'