Enantiopure 2-(2-ethylhexyl)dinaphtho[2,3-<i>b</i>:2',3'-<i>f</i>]thieno[3,2-<i>b</i>]thiophenes: synthesis, single-crystal structure and a surprising lack of influence of stereoisomerism on thin-film structure and electronic properties.
Sumitomo, Kenta; Sudo, Yuta; Kanazawa, Kiseki; Kawabata, Kohsuke; Takimiya, Kazuo; Materials horizons 9 (2022) 444–451; doi:10.1039/d1mh01119g

data_1565123
_publ_section_title
;
 Enantiopure
 2-(2-ethylhexyl)dinaphtho[2,3-<i>b</i>:2',3'-<i>f</i>]thieno[3,2-<i>b</i>]thiophenes:
 synthesis, single-crystal structure and a surprising lack of influence of
 stereoisomerism on thin-film structure and electronic properties.
;
_journal_issue                   1
_journal_name_full               'Materials horizons'
_journal_page_first              444
_journal_page_last               451
_journal_paper_doi               10.1039/d1mh01119g
_journal_volume                  9
_journal_year                    2022
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C30 H28 S2'
_chemical_formula_sum            'C30 H28 S2'
_chemical_formula_weight         452.64
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2021-07-13
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_audit_update_record
;
2021-07-14 deposited with the CCDC.	2021-11-03 downloaded from the CCDC.
;
_cell_angle_alpha                98.542(2)
_cell_angle_beta                 94.452(2)
_cell_angle_gamma                92.932(2)
_cell_formula_units_Z            2
_cell_length_a                   6.01730(10)
_cell_length_b                   8.1041(2)
_cell_length_c                   24.3262(5)
_cell_measurement_reflns_used    19745
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      72.3550
_cell_measurement_theta_min      1.8740
_cell_volume                     1167.20(4)
_computing_cell_refinement       'CrysAlisPro 1.171.40.82a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.82a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.82a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.944
_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    -37.00  95.00   0.50    0.75    --   41.55   0.00  60.00  264
  2  \w     39.00 141.00   0.50    0.75    --   68.00  78.00  11.98  204
  3  \w     72.00 175.00   0.50    3.00    --  106.13 132.00-124.00  206
  4  \w     69.00 115.00   0.50    0.75    --   41.55 136.00  53.00   92
  5  \w     69.00 175.00   0.50    3.00    --  106.13 136.00  53.00  212
  6  \w     28.00 130.00   0.50    0.75    --   56.00  75.00 -26.19  204
  7  \w     37.00 141.00   0.50    0.75    --   68.00  81.00  77.94  208
  8  \w     33.00 138.00   0.50    0.75    --   64.00  81.00 -90.12  210
  9  \w     32.00  71.00   0.50    3.00    --  106.13 -61.00 -60.00   78
 10  \w     32.00 120.00   0.50    3.00    --  106.13-136.00 -10.00  176
 11  \w     33.00 105.00   0.50    3.00    --  106.13 -94.00-180.00  144
 12  \w     33.00 105.00   0.50    3.00    --  106.13 -94.00-150.00  144
 13  \w     23.00 102.00   0.50    0.75    --   41.55-136.00 -10.00  158
 14  \w     33.00 112.00   0.50    3.00    --  106.13-125.00   0.00  158
 15  \w     32.00  71.00   0.50    3.00    --  106.13 -61.00 150.00   78
 16  \w     32.00 117.00   0.50    3.00    --  106.13-132.00 166.00  170
 17  \w     33.00 105.00   0.50    3.00    --  106.13 -94.00  30.00  144
 18  \w     21.00  99.00   0.50    0.75    --   41.55-132.00 166.00  156
 19  \w     20.00 115.00   0.50    0.75    --   41.55  57.00 150.00  190
 20  \w     26.00 130.00   0.50    0.75    --   56.00  80.00  62.49  208
 21  \w     35.00 138.00   0.50    0.75    --   64.00  77.00 -88.01  206
 22  \w     20.00 115.00   0.50    0.75    --   41.55  57.00-150.00  190
 23  \w     22.00 126.00   0.50    0.75    --   52.00  79.00-130.60  208
 24  \w     19.00 122.00   0.50    0.75    --   48.00  77.00-164.86  206
 25  \w     18.00 122.00   0.50    0.75    --   48.00  79.00  32.59  208
 26  \w     18.00 122.00   0.50    0.75    --   48.00  80.00 126.33  208
 27  \w     10.00  36.00   0.50    0.75    --   44.00  88.00  -5.53   52
 28  \w     10.00  36.00   0.50    0.75    --   44.00  89.00 -77.20   52
 29  \w     26.00 130.00   0.50    0.75    --   56.00  80.00-126.07  208
 30  \w     -1.00  27.00   0.50    0.75    --   36.00  94.00 140.98   56
 31  \w    -37.00 120.00   0.50    0.75    --   41.55   0.00  30.00  314
 32  \w    -37.00 120.00   0.50    0.75    --   41.55   0.00-180.00  314
 33  \w    -37.00 120.00   0.50    0.75    --   41.55   0.00-150.00  314
 34  \w    -37.00 120.00   0.50    0.75    --   41.55   0.00-120.00  314
 35  \w    -37.00 120.00   0.50    0.75    --   41.55   0.00 -90.00  314
 36  \w    -37.00 120.00   0.50    0.75    --   41.55   0.00 -60.00  314
 37  \w    -37.00 120.00   0.50    0.75    --   41.55   0.00 -30.00  314
 38  \w    -37.00 120.00   0.50    0.75    --   41.55   0.00   0.00  314
 39  \w    -51.00 -24.00   0.50    3.00    -- -100.00  45.00-180.00   54
 40  \w    -71.00 -26.00   0.50    3.00    -- -100.00  61.00 -90.00   90
 41  \w    -71.00 -26.00   0.50    3.00    -- -100.00  61.00  30.00   90
 42  \w    -51.00 -24.00   0.50    3.00    -- -100.00  45.00  90.00   54
 43  \w    -71.00 -26.00   0.50    3.00    -- -100.00  61.00 120.00   90
 44  \w   -101.00 -29.00   0.50    0.75    --  -41.55 136.00  53.00  144
 45  \w   -106.00 -26.00   0.50    3.00    -- -100.00  77.00  60.00  160
 46  \w    -99.00 -27.00   0.50    0.75    --  -41.55 132.00-124.00  144
 47  \w   -115.00 -19.00   0.50    0.75    --  -41.55 -57.00  60.00  192
 48  \w   -119.00 -18.00   0.50    0.75    --  -41.55 -37.00  90.00  202
 49  \w   -115.00 -13.00   0.50    0.75    --  -41.55 -77.00 -30.00  204
 50  \w   -115.00 -19.00   0.50    0.75    --  -41.55 -57.00   0.00  192
 51  \w   -138.00 -39.00   0.50    0.75    --  -64.00 -66.00 127.26  198
 52  \w   -141.00 -38.00   0.50    0.75    --  -68.00 -78.00 -52.09  206
 53  \w   -141.00 -42.00   0.50    0.75    --  -68.00 -70.00  66.08  198
 54  \w   -141.00 -38.00   0.50    0.75    --  -68.00 -78.00 130.51  206
 55  \w   -141.00 -41.00   0.50    0.75    --  -68.00 -72.00  -9.30  200
 56  \w   -141.00 -42.00   0.50    0.75    --  -68.00 -69.00  78.97  198
 57  \w   -141.00 -43.00   0.50    0.75    --  -68.00 -68.00 165.31  196
 58  \w   -146.00 -46.00   0.50    3.00    --  -72.00 -69.00  98.13  200
 59  \w   -146.00 -49.00   0.50    3.00    --  -72.00 -62.00  15.75  194
 60  \w   -150.00 -46.00   0.50    3.00    --  -76.00 -78.00  26.10  208
 61  \w   -150.00 -48.00   0.50    3.00    --  -76.00 -74.00-149.73  204
 62  \w   -154.00 -52.00   0.50    3.00    --  -80.00 -74.00 -21.79  204
 63  \w   -150.00 -52.00   0.50    3.00    --  -76.00 -64.00 167.30  196
 64  \w   -158.00 -60.00   0.50    3.00    --  -84.00 -65.00  41.22  196
 65  \w   -158.00 -57.00   0.50    3.00    --  -84.00 -72.00-153.83  202
 66  \w   -158.00 -60.00   0.50    3.00    --  -84.00 -64.00  -3.91  196
 67  \w   -162.00 -59.00   0.50    3.00    --  -88.00 -77.00 108.35  206
 68  \w   -162.00 -61.00   0.50    3.00    --  -88.00 -72.00 -95.14  202
 69  \w   -162.00 -60.00   0.50    3.00    --  -88.00 -75.00  31.71  204
 70  \w   -162.00 -57.00   0.50    3.00    --  -88.00 -81.00 161.77  210
 71  \w   -174.00 -78.00   0.50    3.00    -- -100.00-132.00 166.00  192
 72  \w   -166.00 -64.00   0.50    3.00    --  -92.00 -74.00 119.87  204
 73  \w   -162.00 -63.00   0.50    3.00    --  -88.00 -66.00 -71.51  198
 74  \w   -162.00 -61.00   0.50    3.00    --  -88.00 -72.00 -72.50  202
 75  \w   -166.00 -64.00   0.50    3.00    --  -92.00 -74.00  92.55  204
 76  \w   -166.00 -68.00   0.50    3.00    --  -92.00 -64.00   1.69  196
 77  \w   -174.00 -75.00   0.50    3.00    -- -100.00-136.00 -10.00  198
 78  \w   -166.00 -64.00   0.50    3.00    --  -92.00 -74.00  31.28  204
 79  \w   -170.00 -73.00   0.50    3.00    --  -96.00 -57.00 -46.30  194
 80  \w   -170.00 -66.00   0.50    3.00    --  -96.00 -80.00 137.11  208
 81  \w   -174.00 -71.00   0.50    3.00    -- -100.00 -77.00 150.00  206
 82  \w   -174.00 -71.00   0.50    3.00    -- -100.00 -77.00  37.01  206
 83  \w   -170.00 -68.00   0.50    3.00    --  -96.00 -74.00-178.36  204
 84  \w   -170.00 -72.00   0.50    3.00    --  -96.00 -61.00-142.14  196
 85  \w   -174.00 -71.00   0.50    3.00    -- -100.00 -77.00 -90.00  206
 86  \w   -174.00 -71.00   0.50    3.00    -- -100.00 -77.00  79.96  206
 87  \w   -174.00 -71.00   0.50    3.00    -- -100.00 -77.00  90.00  206
 88  \w   -174.00 -77.00   0.50    3.00    -- -100.00 -63.00 153.73  194
 89  \w   -174.00 -71.00   0.50    3.00    -- -100.00 -77.00   0.00  206
 90  \w   -174.00 -76.00   0.50    3.00    -- -100.00 -61.00-150.00  196
 91  \w   -174.00 -73.00   0.50    3.00    -- -100.00 -73.00-114.11  202
 92  \w   -174.00 -77.00   0.50    3.00    -- -100.00 -57.00 -75.02  194
 93  \w   -174.00 -71.00   0.50    3.00    -- -100.00 -77.00-150.00  206
 94  \w   -174.00 -72.00   0.50    3.00    -- -100.00 -74.00 -39.00  204
 95  \w   -120.00 -29.00   0.50    3.00    -- -100.00 136.00  53.00  182
 96  \w   -116.00 -27.00   0.50    3.00    -- -100.00 132.00-124.00  178
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom DW system, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0805
_diffrn_reflns_av_unetI/netI     0.0396
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.944
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            64806
_diffrn_reflns_point_group_measured_fraction_full 0.970
_diffrn_reflns_point_group_measured_fraction_max 0.896
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.095
_diffrn_reflns_theta_min         1.843
_exptl_absorpt_coefficient_mu    2.168
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.61446
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.82a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.288
_exptl_crystal_description       plate
_exptl_crystal_F_000             480
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.01
_refine_diff_density_max         1.128
_refine_diff_density_min         -0.668
_refine_diff_density_rms         0.090
_refine_ls_abs_structure_details
;
 Flack x determined using 3478 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.035(12)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.090
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     581
_refine_ls_number_reflns         8628
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.090
_refine_ls_R_factor_all          0.0650
_refine_ls_R_factor_gt           0.0622
_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^)+(0.1046P)^2^+0.9464P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1662
_refine_ls_wR_factor_ref         0.1684
_reflns_Friedel_coverage         0.898
_reflns_Friedel_fraction_full    0.942
_reflns_Friedel_fraction_max     0.847
_reflns_number_gt                8273
_reflns_number_total             8628
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1mh01119g2.cif
_cod_data_source_block           210712_r-eh-dntt_2
_cod_depositor_comments
'Adding full bibliography for 1565122--1565123.cif.'
_cod_database_code               1565123
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.979
_shelx_estimated_absorpt_t_min   0.613
_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:
 C019(H019), C01A(H01Q)
2.b Secondary CH2 refined with riding coordinates:
 C00Y(H00A,H00B), C00Z(H00D,H00F), C01H(H01T,H01U), C01I(H01A,H01C), C01J(H01D,
 H01E), C01K(H01F,H01H), C01M(H01V,H01W), C01N(H01X,H01Y), C01O(H01Z,H),
 C01P(H01L,H01M)
2.c Aromatic/amide H refined with riding coordinates:
 C005(H005), C009(H009), C00C(H00C), C00E(H00E), C00G(H00G), C00M(H00M),
 C00N(H00N), C00O(H00O), C00P(H00P), C00Q(H00Q), C00V(H00V), C011(H011),
 C013(H013), C014(H014), C015(H015), C016(H016), C017(H017), C018(H018),
 C01B(H01B), C01C(H01R), C01D(H01S), C01G(H01G)
2.d Idealised Me refined as rotating group:
 C01L(H01I,H01J,H01K), C01Q(H01,HA,HB), C01R(H01N,H01O,H01P), C01S(H1,HC,HD)
;
_shelx_res_checksum              10075
_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
;