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_1520540
_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_compound_source        'University of Manchester'
_chemical_formula_moiety         'C30 H39 B1 Br2 N2 S3'
_chemical_formula_sum            'C30 H39 B Br2 N2 S3'
_chemical_formula_weight         694.47
_chemical_name_systematic
6,6-dibromo-8-octyl-3-(5-octylthiophen-2-yl)-6H-5,9-dithia-4,5al4-diaza-6l4-boracyclopenta[e]acenaphthylene
_chemical_properties_physical    'Air-sensitive, Moisture-sensitive'
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_audit_update_record
;
2015-04-30 deposited with the CCDC.
2015-06-12 downloaded from the CCDC.
;
_cell_angle_alpha                65.908(2)
_cell_angle_beta                 79.793(2)
_cell_angle_gamma                68.090(2)
_cell_formula_units_Z            2
_cell_length_a                   10.2773(4)
_cell_length_b                   12.1331(4)
_cell_length_c                   14.8059(4)
_cell_measurement_reflns_used    12035
_cell_measurement_temperature    250
_cell_measurement_theta_max      69.2510
_cell_measurement_theta_min      3.2490
_cell_volume                     1563.00(10)
_computing_cell_refinement       'Apex2 (Bruker AXS, 2006)'
_computing_data_collection       'Apex2 (Bruker AXS, 2006)'
_computing_data_reduction        'CrysAlis, (Oxford Diffraction, 2002)'
_computing_molecular_graphics    'Ortep3 v. 2.02 (LJ Farrugia, 1997)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_solution    'SHELXS 86 (Sheldrick, 1986)'
_diffrn_ambient_temperature      250
_diffrn_measured_fraction_theta_full 0.949
_diffrn_measured_fraction_theta_max 0.949
_diffrn_measurement_details
;
  1 omega  -99.29   87.71   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -70.0000   73.8672 -110.7900 187

  2 phi    -25.79  333.49   1.0008   10.0000
omega____ theta____ kappa____ phi______ frames
 -60.8304  -80.0000   73.8672     -     359

  3 omega   70.77  254.77   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      100.0000   73.8672  109.2097 184

  4 phi    -25.79  332.49   1.0008   10.0000
omega____ theta____ kappa____ phi______ frames
  46.9997   40.0000   73.8672     -     358

  5 phi     55.44  244.59   1.0008   10.0000
omega____ theta____ kappa____ phi______ frames
 -15.5203  -80.0000   73.8672     -     189

  6 phi    -25.79  333.43   1.0006   10.0000
omega____ theta____ kappa____ phi______ frames
 175.3296   90.0000   73.8672     -     359

  7 omega   73.21  153.21   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      103.0000   73.8672   29.2103 80

  8 omega  -44.29  143.70   0.9999   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -15.0000   73.8672   84.2094 188

  9 omega   92.38  199.38   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      105.0000   73.8672  139.2102 107

 10 phi     91.20  332.39   1.0008   10.0000
omega____ theta____ kappa____ phi______ frames
  71.7296   45.0000   73.8672     -     241

 11 omega  115.19  210.19   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       90.0000   73.8672   49.2102 95

 12 phi     22.83   99.88   1.0006   10.0000
omega____ theta____ kappa____ phi______ frames
 -35.6703  -30.0000   73.8672     -     77

 13 omega  104.58  235.58   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       95.0000   73.8672  -80.7911 131

 14 omega  102.32  221.32   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       80.0000   73.8672  114.2098 119

 15 omega   16.90  148.90   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       45.5000   73.8672  -35.7911 132

 16 omega   16.21  154.20   0.9999   10.0000
omega____ theta____ kappa____ phi______ frames
    -       45.5000   73.8672 -145.7909 138

;
_diffrn_measurement_device_type
'Saxi-CrysAlisPro-abstract goniometer imported SAXI images'
_diffrn_measurement_method       '\w and \p scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Cu) X-ray Source'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.054
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            4499
_diffrn_reflns_theta_full        60.672
_diffrn_reflns_theta_max         60.672
_diffrn_reflns_theta_min         3.271
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    5.326
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.73541
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.476
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             712
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.015
_exptl_crystal_size_min          0.001
_refine_diff_density_max         3.22
_refine_diff_density_min         -0.70
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   0.9579
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     343
_refine_ls_number_reflns         4455
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0739
_refine_ls_R_factor_gt           0.0662
_refine_ls_shift/su_max          0.0006789
_refine_ls_shift/su_mean         0.0000527
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) 
 [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] 
 where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax 
 Method = Robust Weighting (Prince, 1982) 
 W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^ 
 A~i~ are: 
 13.4 20.6 9.48 2.22 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1739
_refine_ls_wR_factor_gt          0.1625
_refine_ls_wR_factor_ref         0.1734
_reflns_limit_h_max              11
_reflns_limit_h_min              -11
_reflns_limit_k_max              13
_reflns_limit_k_min              -12
_reflns_limit_l_max              16
_reflns_limit_l_min              0
_reflns_number_gt                3886
_reflns_number_total             4499
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   3.47
_oxford_diffrn_Wilson_scale      160.32
_oxford_refine_ls_r_factor_ref   0.0735
_oxford_refine_ls_scale          0.07981(4)
_oxford_reflns_number_all        4472
_oxford_reflns_threshold_expression_ref I>0.0\s(I)
_cod_data_source_file            c5sc01800e2.cif
_cod_data_source_block           1
_cod_depositor_comments
'Adding full bibliography for 1520535--1520540.cif.'
_cod_original_sg_symbol_H-M      'P -1 '
_cod_original_formula_sum        'C30 H39 B1 Br2 N2 S3'
_cod_database_code               1520540
_iucr_refine_instruction_details_constraints
;
BLOCK SCALE X'S, U'S 
RIDE C   (  10,X'S) H   ( 101,X'S) 
RIDE C   (  11,X'S) H   ( 111,X'S) 
RIDE C   (  16,X'S) H   ( 161,X'S) H   ( 162,X'S) 
RIDE C   (  17,X'S) H   ( 171,X'S) H   ( 172,X'S) 
RIDE C   (  18,X'S) H   ( 181,X'S) H   ( 182,X'S) 
RIDE C   (  19,X'S) H   ( 191,X'S) H   ( 192,X'S) 
RIDE C   (  20,X'S) H   ( 201,X'S) H   ( 202,X'S) 
RIDE C   (  21,X'S) H   ( 211,X'S) H   ( 212,X'S) 
RIDE C   (  22,X'S) H   ( 221,X'S) H   ( 222,X'S) 
RIDE C   (  23,X'S) H   ( 231,X'S) H   ( 232,X'S) H   ( 233,X'S) 
RIDE C   (  24,X'S) H   ( 241,X'S) 
RIDE C   (  25,X'S) H   ( 251,X'S) 
RIDE C   (  28,X'S) H   ( 281,X'S) 
RIDE C   (  31,X'S) H   ( 311,X'S) H   ( 312,X'S) 
RIDE C   (  32,X'S) H   ( 321,X'S) H   ( 322,X'S) 
RIDE C   (  33,X'S) H   ( 331,X'S) H   ( 332,X'S) 
RIDE C   (  34,X'S) H   ( 341,X'S) H   ( 342,X'S) 
RIDE C   (  35,X'S) H   ( 351,X'S) H   ( 352,X'S) 
RIDE C   (  36,X'S) H   ( 361,X'S) H   ( 362,X'S) 
RIDE C   (  37,X'S) H   ( 371,X'S) H   ( 372,X'S) 
RIDE C   (  38,X'S) H   ( 381,X'S) H   ( 382,X'S) H   ( 383,X'S) 
END                                                                             
;
_iucr_refine_instruction_details_restraints
;
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
;