Synthesis of bent-shaped π-extended thienoacenes from 2,5-distannylated 3,4-dialkynethiophene.
Agrawal, Abhijeet R.; Kumar, Neha Rani; Choudhury, Aditya; Zade, Sanjio S.; Chemical communications (Cambridge, England) 57 (2021) 9538–9541; doi:10.1039/d1cc04283a

data_7128857
_publ_section_title
;
 Synthesis of bent-shaped \p-extended thienoacenes from 2,5-distannylated
 3,4-dialkynethiophene.
;
_journal_issue                   75
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              9538
_journal_page_last               9541
_journal_paper_doi               10.1039/d1cc04283a
_journal_volume                  57
_journal_year                    2021
_chemical_formula_moiety         'C44 H36 S'
_chemical_formula_sum            'C44 H36 S'
_chemical_formula_weight         596.79
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2020-12-07
_audit_creation_method
;
Olex2 1.3-ac4
(compiled 2019.04.23 svn.r3594 for Rigaku Oxford Diffraction, GUI svn.r5739)
;
_audit_update_record
;
2020-12-31 deposited with the CCDC.	2021-08-18 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 101.5840(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.8904(2)
_cell_length_b                   7.48810(10)
_cell_length_c                   31.9207(4)
_cell_measurement_reflns_used    18951
_cell_measurement_temperature    99.99(10)
_cell_measurement_theta_max      66.0970
_cell_measurement_theta_min      2.7710
_cell_volume                     3018.37(7)
_computing_cell_refinement       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_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_environment      N~2~
_diffrn_ambient_temperature      99.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 7.9580
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_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     57.00 120.00   0.75    1.50    --   26.33 178.00   0.00   84
  2  \w    -12.00 102.00   0.75    1.50    --   26.33  57.00 120.00  152
  3  \w    -12.00 102.00   0.75    1.50    --   26.33  57.00-120.00  152
  4  \w    -12.00 102.00   0.75    1.50    --   26.33  57.00   0.00  152
  5  \w     55.00 121.00   0.75    1.50    --   26.33-178.00 120.00   88
  6  \w    100.00 152.50   0.75    1.50    --   67.17 111.00 -60.00   70
  7  \w    -12.00 114.00   0.75    1.50    --   67.17 -45.00-180.00  168
  8  \w     20.00 146.00   0.75    1.50    --   67.17  45.00  60.00  168
  9  \w     -9.00 103.50   0.75    1.50    --   67.17 -61.00   0.00  150
 10  \w     12.00 115.50   0.75    1.50    --   67.17-111.00-180.00  138
 11  \w    -21.00 153.00   0.75    1.50    --   67.17 -15.00   0.00  232
 12  \w     57.00 150.00   0.75    1.50    --   67.17 178.00 -60.00  124
 13  \w    100.00 152.50   0.75    1.50    --   67.17 111.00  90.00   70
 14  \w     -4.00 108.50   0.75    1.50    --   67.17 -94.00 -90.00  150
 15  \w     36.00 177.00   0.75    1.50    --  108.00  32.00   0.00  188
 16  \w    101.00 177.50   0.75    1.50    --  108.00 104.00  30.00  102
 17  \w     25.00 178.00   0.75    1.50    --  108.00 -32.00 -30.00  204
 18  \w     25.00 118.00   0.75    1.50    --  108.00-119.00  81.15  124
 19  \w    101.00 177.50   0.75    1.50    --  108.00 104.00  60.00  102
 20  \w     23.00 150.50   0.75    1.50    --  108.00 -77.00   0.00  170
 21  \w     28.00 157.00   0.75    1.50    --  108.00 -43.00  90.00  172
 22  \w     19.00 157.00   0.75    1.50    --  108.00 -89.00-120.00  184
 23  \w     25.00 144.25   0.75    1.50    --  108.00 -32.00 120.00  159
 24  \w    112.00 167.50   0.75    1.50    --  108.00 138.00  90.00   74
 25  \w     90.50 116.00   0.75    1.50    --  108.00-111.00  -1.10   34
 26  \w     49.00  75.25   0.75    1.50    --  108.00  32.00  90.00   35
 27  \w     89.00 174.50   0.75    1.50    --  108.00  32.00  90.00  114
 28  \w     42.00  96.00   0.75    1.50    --  108.00-104.00-120.00   72
 29  \w     29.00  55.25   0.75    1.50    --  108.00 -77.00-120.00   35
 30  \w     31.00  67.00   0.75    1.50    --  108.00  11.00 -90.00   48
 31  \w     99.00 125.25   0.75    1.50    --  108.00 -65.00 -90.00   35
 32  \w     30.00  74.25   0.75    1.50    --  108.00 -65.00 -90.00   59
 33  \w     79.00 105.25   0.75    1.50    --  108.00 -45.00 108.84   35
 34  \w    115.00 177.25   0.75    1.50    --  108.00 104.00 150.00   83
 35  \w    120.00 146.25   0.75    1.50    --  108.00 138.00   0.00   35
 36  \w     21.00 102.00   0.75    1.50    --  108.00-104.00  90.00  108
 37  \w    105.00 137.25   0.75    1.50    --  108.00 104.00 -90.00   43
 38  \w    131.00 177.50   0.75    1.50    --  108.00 104.00 -60.00   62
 39  \w     82.00 108.25   0.75    1.50    --  108.00 -54.00  60.00   35
 40  \w     84.00 129.00   0.75    1.50    --  108.00 -77.00-120.00   60
 41  \w     90.00 116.25   0.75    1.50    --  108.00 138.00   0.00   35
 42  \w    102.00 128.25   0.75    1.50    --  108.00 104.00-180.00   35
 43  \w    129.00 155.25   0.75    1.50    --  108.00 104.00-180.00   35
 44  \w     31.00  67.00   0.75    1.50    --  108.00 -54.00  60.00   48
 45  \w     21.00  94.50   0.75    1.50    --  108.00-104.00  30.00   98
 46  \w     72.00 112.50   0.75    1.50    --  108.00-104.00   0.00   54
 47  \w    102.00 139.50   0.75    1.50    --  108.00 104.00-150.00   50
 48  \w     29.00  55.25   0.75    1.50    --  108.00 -45.00 108.84   35
 49  \w    129.00 155.25   0.75    1.50    --  108.00 138.00 -90.00   35
 50  \w     29.00 113.00   0.75    1.50    --  108.00-115.00 -51.13  112
 51  \w     87.00 113.25   0.75    1.50    --  108.00  65.00 -90.00   35
 52  \w     27.00 121.50   0.75    1.50    --  108.00-125.00-163.64  126
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0350283000
_diffrn_orient_matrix_UB_12      0.0987504000
_diffrn_orient_matrix_UB_13      -0.0371572000
_diffrn_orient_matrix_UB_21      0.1149547000
_diffrn_orient_matrix_UB_22      0.0029783000
_diffrn_orient_matrix_UB_23      0.0254614000
_diffrn_orient_matrix_UB_31      0.0210271000
_diffrn_orient_matrix_UB_32      -0.1804613000
_diffrn_orient_matrix_UB_33      -0.0199312000
_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  0.0266
_diffrn_reflns_av_unetI/netI     0.0153
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_number            28335
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        66.522
_diffrn_reflns_theta_max         66.522
_diffrn_reflns_theta_min         4.030
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.186
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.68710
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.67a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear yellowish yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.313
_exptl_crystal_description       block
_exptl_crystal_F_000             1264
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.260
_refine_diff_density_min         -0.287
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     408
_refine_ls_number_reflns         5254
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.065
_refine_ls_R_factor_all          0.0347
_refine_ls_R_factor_gt           0.0338
_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^)+(0.0429P)^2^+1.5763P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0870
_refine_ls_wR_factor_ref         0.0875
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5145
_reflns_number_total             5254
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1cc04283a2.cif
_cod_data_source_block           phen_acene_lt_a
_cod_depositor_comments          'Adding full bibliography for 7128857.cif.'
_cod_database_code               7128857
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H S'
_shelx_estimated_absorpt_t_max   0.797
_shelx_estimated_absorpt_t_min   0.717
_reflns_odcompleteness_completeness 97.71
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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:
 C00L(H00A,H00B), C00Q(H00C,H00D), C00T(H00E,H00F), C00Y(H00G,H00H), C010(H01A,
 H01B), C018(H01F,H01G)
2.b Aromatic/amide H refined with riding coordinates:
 C006(H006), C00I(H00I), C00N(H00N), C00O(H00O), C00P(H00P), C00R(H00R),
 C00S(H00S), C00U(H00U), C00V(H00V), C00W(H00W), C00X(H00X), C00Z(H00Z),
 C011(H011), C012(H012), C013(H013), C014(H014), C016(H016), C017(H017)
2.c Idealised Me refined as rotating group:
 C015(H01C,H01D,H01E), C019(H01H,H01I,H01J)
;
_shelx_res_checksum              58041
_shelx_hkl_checksum              61496
_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 1.493
_oxdiff_exptl_absorpt_empirical_full_min 0.756