Enhancing electron affinity and tuning band gap in donor–acceptor organic semiconductors by benzothiadiazole directed C–H borylation
Crossley, D. L.; Cade, I. A.; Clark, E. R.; Escande, A.; Humphries, M. J.; King, S. M.; Vitorica-Yrezabal, I.; Ingleson, M. J.; Turner, M. L.; Chem. Sci. 6 (2015) 5144–; doi:10.1039/C5SC01800E

data_1520539
_publ_section_title
;
 Enhancing electron affinity and tuning band gap in donor--acceptor
 organic semiconductors by benzothiadiazole directed C--H borylation
;
_journal_issue                   9
_journal_name_full               'Chem. Sci.'
_journal_page_first              5144
_journal_paper_doi               10.1039/C5SC01800E
_journal_volume                  6
_journal_year                    2015
_chemical_formula_moiety         'C32 H45 B N2 S3'
_chemical_formula_sum            'C32 H45 B N2 S3'
_chemical_formula_weight         564.69
_chemical_name_systematic
6,6-dimethyl-8-octyl-3-(5-octylthiophen-2-yl)-6H-5,9-dithia-4,5al4-diaza-6l4-boracyclopenta[e]acenaphthylene
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2015-04-29
_audit_creation_method
;
Olex2 1.2
(compiled 2014.05.21 svn.r2940 for OlexSys, GUI svn.r4846)
;
_audit_update_record
;
2015-04-30 deposited with the CCDC.
2015-06-12 downloaded from the CCDC.
;
_cell_angle_alpha                98.640(7)
_cell_angle_beta                 95.792(8)
_cell_angle_gamma                101.670(8)
_cell_formula_units_Z            2
_cell_length_a                   6.5240(6)
_cell_length_b                   13.6675(11)
_cell_length_c                   18.0034(17)
_cell_measurement_reflns_used    4548
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      74.1330
_cell_measurement_theta_min      2.5190
_cell_volume                     1539.9(2)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.15
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.962
_diffrn_measured_fraction_theta_max 0.918
_diffrn_measurement_details
;
  1 phi    -25.61  322.24   1.4994   20.0000
omega____ theta____ kappa____ phi______ frames
 -86.4503  -75.0000   73.8669     -     232

  2 phi    -18.89  310.97   1.4994   30.0000
omega____ theta____ kappa____ phi______ frames
  89.2097  113.0000   73.8669     -     220

  3 phi     31.35  263.75   1.4994   30.0000
omega____ theta____ kappa____ phi______ frames
 141.7597   90.0000   73.8669     -     155

  4 omega   81.21  267.21   1.5000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      110.0000   73.8669   74.2100 124

  5 omega   83.21  267.71   1.5000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   73.8669 -170.7919 123

  6 omega   90.64  261.64   1.5000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      110.0000   73.8669  -40.7906 114

  7 phi   -112.90  101.51   1.4994   10.0000
omega____ theta____ kappa____ phi______ frames
  76.6294   50.5000   73.8669     -     143

  8 omega   82.94  217.94   1.5000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      105.0000   73.8669  144.2081 90

  9 omega  144.01  223.51   1.5000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       70.0000   73.8669  -75.7912 53

 10 phi     35.03  151.98   1.4994   30.0000
omega____ theta____ kappa____ phi______ frames
 124.3394  110.5000   73.8669     -     78

 11 omega   89.96  200.96   1.5000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      100.0000   73.8669 -125.7919 74

 12 phi    -21.42   91.03   1.4994   20.0000
omega____ theta____ kappa____ phi______ frames
  45.0897  -70.0000   73.8669     -     75

 13 omega  136.77  247.77   1.5000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000   73.8669 -110.7906 74

 14 omega   38.71  152.71   1.5000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       68.0000   73.8669  154.2094 76

 15 omega  -62.37   35.13   1.5000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.0000   73.8669   54.2081 65

 16 omega  -12.64   66.86   1.5000   10.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   73.8669 -135.7906 53

 17 omega   73.20  154.20   1.5000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      100.5000   73.8669  -78.2912 54

 18 omega   82.11  190.11   1.5000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   73.8669   39.2088 72
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type
'Saxi-CrysAlisPro-abstract goniometer imported SAXI images'
_diffrn_measurement_method       '\w and \p scans'
_diffrn_orient_matrix_UB_11      -0.0411638000
_diffrn_orient_matrix_UB_12      -0.0178136000
_diffrn_orient_matrix_UB_13      0.0801953000
_diffrn_orient_matrix_UB_21      -0.0829100000
_diffrn_orient_matrix_UB_22      -0.1142215000
_diffrn_orient_matrix_UB_23      -0.0306313000
_diffrn_orient_matrix_UB_31      0.2250798000
_diffrn_orient_matrix_UB_32      -0.0173904000
_diffrn_orient_matrix_UB_33      0.0161929000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0768
_diffrn_reflns_av_unetI/netI     0.0563
_diffrn_reflns_Laue_measured_fraction_full 0.962
_diffrn_reflns_Laue_measured_fraction_max 0.918
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            17172
_diffrn_reflns_point_group_measured_fraction_full 0.962
_diffrn_reflns_point_group_measured_fraction_max 0.918
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.355
_diffrn_reflns_theta_min         2.506
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.364
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.53401
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
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    1.218
_exptl_crystal_description       needle
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.656
_refine_diff_density_min         -0.562
_refine_diff_density_rms         0.095
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     347
_refine_ls_number_reflns         5846
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.1247
_refine_ls_R_factor_gt           0.0868
_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^)+(0.1355P)^2^+2.0701P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2351
_refine_ls_wR_factor_ref         0.2689
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3846
_reflns_number_total             5846
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5sc01800e2.cif
_cod_data_source_block           xmji63
_cod_depositor_comments
'Adding full bibliography for 1520535--1520540.cif.'
_cod_database_code               1520539
_shelxl_version_number           2014/6
_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:
 C8(H8A,H8B), C9(H9A,H9B), C12(H12A,H12B), C15(H15A,H15B), C16(H16A,H16B),
 C18(H18A,H18B), C21(H21A,H21B), C22(H22A,H22B), C27(H27A,H27B), C28(H28A,H28B),
  C30(H30A,H30B), C31(H31A,H31B), C34(H34A,H34B), C35(H35A,H35B)
2.b Aromatic/amide H refined with riding coordinates:
 C14(H14), C17(H17), C19(H19), C24(H24), C25(H25)
2.c Idealised Me refined as rotating group:
 C23(H23A,H23B,H23C), C26(H26A,H26B,H26C), C29(H29A,H29B,H29C), C32(H32A,H32B,
 H32C)
;
_shelx_res_checksum              25612
_shelx_hkl_checksum              66143
_olex2_submission_special_instructions 'No special instructions were received'