Trisulfur radical anion-triggered stitching thienannulation: rapid access to largely π-extended thienoacenes
Su, Feng; Chen, Shuqi; Mo, Xiaogang; Wu, Kongchuan; Wu, Jiajun; Lin, Weidong; Lin, Zhiwei; Lin, Jianbin; Zhang, Hui-Jun; Wen, Ting-Bin; Chemical Science 11 (2020) 1503–1509; doi:10.1039/C9SC05332H

data_1556704
_publ_section_title
;
 Trisulfur radical anion-triggered stitching thienannulation: rapid access
 to largely \p-extended thienoacenes
;
_journal_issue                   6
_journal_name_full               'Chemical Science'
_journal_page_first              1503
_journal_page_last               1509
_journal_paper_doi               10.1039/C9SC05332H
_journal_volume                  11
_journal_year                    2020
_chemical_formula_moiety         '2(C18.5 N2 O4 S1.5)'
_chemical_formula_sum            'C37 N4 O8 S3'
_chemical_formula_weight         724.59
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_audit_creation_date             2019-10-15
_audit_creation_method
;
Olex2 1.3
(compiled 2019.09.11 svn.r3662 for OlexSys, GUI svn.r5938)
;
_audit_update_record
;
2019-10-22 deposited with the CCDC.	2019-12-20 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 102.198(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   22.0328(10)
_cell_length_b                   21.2168(7)
_cell_length_c                   33.589(3)
_cell_measurement_reflns_used    6340
_cell_measurement_temperature    100.00(11)
_cell_measurement_theta_max      65.8410
_cell_measurement_theta_min      4.0990
_cell_volume                     15347.2(16)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL 2014/7 (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(11)
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.960
_diffrn_measured_fraction_theta_max 0.910
_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    146.00 178.00   1.00  107.00    --  104.28  63.00 -67.00   32
  2  \w    -68.00  32.00   1.00   30.00    --  -38.95  63.00 -67.00  100
  3  \w     60.00 116.00   1.00   30.00    --   38.95 178.00 120.00   56
  4  \w     75.00 142.00   1.00  107.00    --  104.28  63.00 -67.00   67
  5  \w     67.00 177.00   1.00  107.00    --  104.28  30.00  30.00  110
  6  \w     31.00 117.00   1.00  107.00    --  104.28-125.00-180.00   86
  7  \w     38.00 112.00   1.00  107.00    --  104.28 -63.00 155.00   74
  8  \w    -68.00 -41.00   1.00  107.00    --  -94.50  63.00 -67.00   27
  9  \w    -82.00 -17.00   1.00  107.00    --  -94.50 125.00  30.00   65
 10  \w   -107.00 -21.00   1.00   30.00    --  -38.95 -63.00 155.00   86
 11  \w   -170.00-101.00   1.00  107.00    --  -94.50 -63.00 155.00   69
 12  \w   -171.00 -70.00   1.00  107.00    --  -94.50-125.00 -60.00  101
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0074161000
_diffrn_orient_matrix_UB_12      0.0380966000
_diffrn_orient_matrix_UB_13      0.0397578000
_diffrn_orient_matrix_UB_21      0.0537706000
_diffrn_orient_matrix_UB_22      0.0374296000
_diffrn_orient_matrix_UB_23      -0.0114358000
_diffrn_orient_matrix_UB_31      -0.0466555000
_diffrn_orient_matrix_UB_32      0.0492323000
_diffrn_orient_matrix_UB_33      -0.0220537000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0885
_diffrn_reflns_av_unetI/netI     0.0795
_diffrn_reflns_Laue_measured_fraction_full 0.960
_diffrn_reflns_Laue_measured_fraction_max 0.910
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       40
_diffrn_reflns_limit_l_min       -41
_diffrn_reflns_number            69097
_diffrn_reflns_point_group_measured_fraction_full 0.961
_diffrn_reflns_point_group_measured_fraction_max 0.910
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.248
_diffrn_reflns_theta_min         3.670
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.557
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.37057
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear dark red'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    0.314
_exptl_crystal_description       block
_exptl_crystal_F_000             1448
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.5
_exptl_crystal_size_min          0.3
_refine_diff_density_max         1.696
_refine_diff_density_min         -1.141
_refine_diff_density_rms         0.089
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.45(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    undef
_refine_ls_matrix_type           full
_refine_ls_number_parameters     908
_refine_ls_number_reflns         45162
_refine_ls_number_restraints     325
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.2265
_refine_ls_R_factor_gt           0.1541
_refine_ls_shift/su_max          0.020
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1000P)^2^+51.1254P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3571
_refine_ls_wR_factor_ref         0.4070
_reflns_Friedel_coverage         0.944
_reflns_Friedel_fraction_full    0.961
_reflns_Friedel_fraction_max     0.910
_reflns_number_gt                22016
_reflns_number_total             45162
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9sc05332h2.cif
_cod_data_source_block           sf-20181007_sq
_cod_depositor_comments
;Adding full bibliography for 1556703--1556704.cif.

 Adding full bibliography for 1556703--1556704.cif.
;
_cod_original_cell_volume        15347.3(15)
_cod_database_code               1556704
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.851
_shelx_estimated_absorpt_t_min   0.768
_reflns_odcompleteness_completeness 96.49
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.55(4)
 0.45(4)
2. Restrained distances
 C3-C2
 1.65 with sigma of 0.001
 N4-C33
 1.47 with sigma of 0.001
 C1A-S2A
 1.728 with sigma of 0.02
 C1A-C2A
 1.329 with sigma of 0.02
 C5A-C1A
 1.47 with sigma of 0.02
 S2A-C1A
 1.75 with sigma of 0.001
 S2A-C4A
 1.75 with sigma of 0.001
 C14A-C5A
 1.384 with sigma of 0.005
 C13A-C14A
 1.522 with sigma of 0.005
 C12A-C13A
 1.383 with sigma of 0.005
 C12A-C7A
 1.337 with sigma of 0.005
 C7A-C6A
 1.605 with sigma of 0.005
 C9A-C8A
 1.414 with sigma of 0.005
 C10A-C9A
 1.477 with sigma of 0.02
 C11A-C10A
 1.272 with sigma of 0.005
 C11A-C12A
 1.584 with sigma of 0.001
 C15A-C13A
 1.315 with sigma of 0.02
 C16A-N1A
 1.237 with sigma of 0.02
 N1A-C19A
 1.5 with sigma of 0.02
 C8A-C7A
 1.4 with sigma of 0.02
 C18A-C8A
 1.38 with sigma of 0.02
 C18A-N2A
 1.47 with sigma of 0.02
 N2A-C17A
 1.32 with sigma of 0.02
 C17A-C6A
 1.552 with sigma of 0.005
 C33A-N4A
 1.423 with sigma of 0.001
 C34A-N4A
 1.473 with sigma of 0.001
 C34A-O7A
 1.49 with sigma of 0.001
 O8A-C33A
 1.3 with sigma of 0.005
 O6A-C31A
 1.3 with sigma of 0.005
 C31A-N3A
 1.487 with sigma of 0.002
 C26A-C25A
 1.45 with sigma of 0.02
 O5A-C32A
 1.38 with sigma of 0.005
 C32A-C27A
 1.373 with sigma of 0.001
 C29A-C31A
 1.458 with sigma of 0.001
 C32A-C28A
 2.59 with sigma of 0.001
 N3A-C32A
 1.51 with sigma of 0.001
 C23A-C28A
 1.44 with sigma of 0.001
 O1A-C16A
 1.2 with sigma of 0.001
 C32A-O5A
 1.132 with sigma of 0.001
 C24-O6
 2.183 with sigma of 0.001
 O5A-C27A
 2.183 with sigma of 0.001
 N3A-O5A
 2.318 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
Uanis(C29) \\sim Ueq, Uanis(C4) \\sim Ueq, Uanis(C2) \\sim Ueq, Uanis(C5) \\sim
Ueq, Uanis(C00N) \\sim Ueq, Uanis(C15) \\sim Ueq: with sigma of 0.001 and sigma
for terminal atoms of 0.002
Uanis(C30) \\sim Ueq, Uanis(C1) \\sim Ueq, Uanis(N3) \\sim Ueq, Uanis(C33)
\\sim Ueq, Uanis(C3) \\sim Ueq, Uanis(C31) \\sim Ueq, Uanis(N4) \\sim Ueq: with
sigma of 0.001 and sigma for terminal atoms of 0.002
Uanis(O2) \\sim Ueq, Uanis(C14) \\sim Ueq, Uanis(C16) \\sim Ueq, Uanis(C10)
\\sim Ueq, Uanis(N2) \\sim Ueq, Uanis(C17) \\sim Ueq, Uanis(C6) \\sim Ueq,
Uanis(C25) \\sim Ueq, Uanis(C26) \\sim Ueq, Uanis(C28) \\sim Ueq, Uanis(C23)
\\sim Ueq, Uanis(C24) \\sim Ueq, Uanis(C22) \\sim Ueq: with sigma of 0.001 and
sigma for terminal atoms of 0.002
Uanis(C33) \\sim Ueq: with sigma of 0.0008 and sigma for terminal atoms of
0.0016
: with sigma of 0.001 and sigma for terminal atoms of 0.002
Uanis(C1A) \\sim Ueq, Uanis(C14A) \\sim Ueq, Uanis(C2A) \\sim Ueq, Uanis(C3A)
\\sim Ueq, Uanis(C30A) \\sim Ueq: with sigma of 0.01 and sigma for terminal
atoms of 0.02
Uanis(C3A) \\sim Ueq, Uanis(C05V) \\sim Ueq: with sigma of 0.001 and sigma for
terminal atoms of 0.002
Uanis(C18A) \\sim Ueq, Uanis(C26A) \\sim Ueq, Uanis(C27A) \\sim Ueq,
Uanis(C28A) \\sim Ueq, Uanis(C29A) \\sim Ueq, Uanis(C34A) \\sim Ueq: with sigma
of 0.01 and sigma for terminal atoms of 0.02
Uanis(C13A) \\sim Ueq: with sigma of 0.02 and sigma for terminal atoms of 0.002
Uanis(C15A) \\sim Ueq: with sigma of 0.001 and sigma for terminal atoms of 0.002
Uanis(C8A) \\sim Ueq, Uanis(C10A) \\sim Ueq: with sigma of 0.02 and sigma for
terminal atoms of 0.005
Uanis(N2A) \\sim Ueq: with sigma of 0.02 and sigma for terminal atoms of 0.005
Uanis(C21A) \\sim Ueq: with sigma of 0.02 and sigma for terminal atoms of 0.005
Uanis(C21A) \\sim Ueq, Uanis(C23A) \\sim Ueq, Uanis(C27A) \\sim Ueq: with sigma
of 0.02 and sigma for terminal atoms of 0.003
Uanis(O2A) \\sim Ueq: with sigma of 0.001 and sigma for terminal atoms of 0.002
Uanis(C11A) \\sim Ueq: with sigma of 0.001 and sigma for terminal atoms of 0.002
4. Others
 Fixed Uiso: C4A(0.2) N3A(0.2) N4A(0.2) C32A(0.1) O5A(0.2)
;
_shelx_res_checksum              57948
_shelx_fab_checksum              2390
_platon_squeeze_void_probe_radius 1.20
_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 2.533
_oxdiff_exptl_absorpt_empirical_full_min 0.638