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_1520538
_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         'C42 H49 B1 N2 S3'
_chemical_formula_sum            'C42 H49 B N2 S3'
_chemical_formula_weight         688.87
_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
;
2015-02-23 deposited with the CCDC.
2015-06-12 downloaded from the CCDC.
;
_cell_angle_alpha                74.649(8)
_cell_angle_beta                 85.857(8)
_cell_angle_gamma                83.373(8)
_cell_formula_units_Z            2
_cell_length_a                   6.3487(6)
_cell_length_b                   16.1168(15)
_cell_length_c                   19.3671(17)
_cell_measurement_reflns_used    2965
_cell_measurement_temperature    220
_cell_measurement_theta_max      57.4720
_cell_measurement_theta_min      2.8780
_cell_volume                     1896.4(3)
_computing_cell_refinement       'CrysAlis, (Oxford Diffraction, 2002)'
_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    'SIR92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      220
_diffrn_measured_fraction_theta_full 0.976
_diffrn_measured_fraction_theta_max 0.916
_diffrn_measurement_details
;
  1 omega -104.76   78.24   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      -74.5162   73.8669  122.2950 183

  2 omega  -99.53   53.47   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      -79.7412   73.8669 -129.6400 153

  3 omega  -87.24   14.76   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      -72.4463   73.8669  -27.6087 102

  4 omega  -89.30   68.70   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      -79.5141   73.8669  179.5438 158

  5 phi    -13.92  167.20   1.0006   59.9980
omega____ theta____ kappa____ phi______ frames
 -13.4163   -2.6263   73.8669     -     181

  6 omega  -91.93   66.07   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      -77.1363   73.8669   79.4963 158

;
_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  0.060
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            4765
_diffrn_reflns_theta_full        51.360
_diffrn_reflns_theta_max         57.604
_diffrn_reflns_theta_min         2.368
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.015
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.34316
_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            purple
_exptl_crystal_density_diffrn    1.206
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.67
_refine_diff_density_min         -0.58
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   0.9336
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     434
_refine_ls_number_reflns         4733
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1482
_refine_ls_R_factor_gt           0.1185
_refine_ls_shift/su_max          0.0006195
_refine_ls_shift/su_mean         0.0001063
_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: 
 0.247E+04 0.415E+04 0.261E+04 0.113E+04 261. 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.3498
_refine_ls_wR_factor_gt          0.3212
_refine_ls_wR_factor_ref         0.3498
_reflns_limit_h_max              6
_reflns_limit_h_min              -6
_reflns_limit_k_max              17
_reflns_limit_k_min              -16
_reflns_limit_l_max              20
_reflns_limit_l_min              0
_reflns_number_gt                3194
_reflns_number_total             4765
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   4.15
_oxford_diffrn_Wilson_scale      0.26
_oxford_refine_ls_r_factor_ref   0.1482
_oxford_refine_ls_scale          2.61(10)
_oxford_reflns_number_all        4733
_oxford_reflns_threshold_expression_ref I>-3.0\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        'C42 H49 B1 N2 S3'
_cod_database_code               1520538
_iucr_refine_instruction_details_constraints
;
BLOCK SCALE X'S, U'S 
SUMFIX ELEMENT SCALES 
RIDE C   (   1,X'S) H   (  11,X'S) H   (  12,X'S) 
RIDE C   (   2,X'S) H   (  21,X'S) 
RIDE C   (   3,X'S) H   (  31,X'S) 
RIDE C   (   4,X'S) H   (  41,X'S) 
RIDE C   (   5,X'S) H   (  51,X'S) 
RIDE C   (   6,X'S) H   (  62,X'S) H   (  61,X'S) 
RIDE C   (   7,X'S) H   (  72,X'S) H   (  71,X'S) 
RIDE C   (   8,X'S) H   (  81,X'S) H   (  82,X'S) 
RIDE C   (  10,X'S) H   ( 101,X'S) 
RIDE C   (  17,X'S) H   ( 171,X'S) 
RIDE C   (  18,X'S) H   ( 181,X'S) 
RIDE C   (  20,X'S) H   ( 201,X'S) 
RIDE C   (  21,X'S) H   ( 211,X'S) 
RIDE C   (  23,X'S) H   ( 232,X'S) H   ( 231,X'S) 
RIDE C   (  24,X'S) H   ( 242,X'S) H   ( 241,X'S) 
RIDE C   (  25,X'S) H   ( 251,X'S) H   ( 252,X'S) 
RIDE C   (  26,X'S) H   ( 262,X'S) H   ( 261,X'S) 
RIDE C   (  27,X'S) H   ( 272,X'S) H   ( 271,X'S) 
RIDE C   (  28,X'S) H   ( 281,X'S) H   ( 282,X'S) 
RIDE C   (  29,X'S) H   ( 291,X'S) H   ( 292,X'S) 
RIDE C   (  30,X'S) H   ( 301,X'S) H   ( 302,X'S) H   ( 303,X'S) 
RIDE C   (  32,X'S) H   ( 321,X'S) 
RIDE C   (  33,X'S) H   ( 331,X'S) 
RIDE C   (  34,X'S) H   ( 341,X'S) 
RIDE C   (  35,X'S) H   ( 351,X'S) 
RIDE C   (  36,X'S) H   ( 361,X'S) 
RIDE C   (  38,X'S) H   ( 381,X'S) 
RIDE C   (  39,X'S) H   ( 391,X'S) 
RIDE C   (  40,X'S) H   ( 401,X'S) 
RIDE C   (  41,X'S) H   ( 411,X'S) 
RIDE C   (  42,X'S) H   ( 421,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                                                                             
;