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_1520537
_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         'C65 H44 B2 F20 N4 S2, 2(C3 H6 O)'
_chemical_formula_sum            'C71 H56 B2 F20 N4 O2 S2'
_chemical_formula_weight         1462.96
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 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                90
_cell_angle_beta                 98.039(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.5445(3)
_cell_length_b                   22.7136(6)
_cell_length_c                   19.7133(5)
_cell_measurement_reflns_used    17711
_cell_measurement_temperature    100
_cell_measurement_theta_max      73.6380
_cell_measurement_theta_min      2.9670
_cell_volume                     6448.4(3)
_computing_cell_refinement       'CrysAlisPro, Agilent Technologies (2013)'
_computing_data_collection       'CrysAlisPro, Agilent Technologies (2013)'
_computing_data_reduction        'CrysAlisPro, Agilent Technologies (2013)'
_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      100
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measurement_details
;
  1 omega   86.01  266.01   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000   73.8672 -125.7912 180

  2 phi      1.35  307.59   1.0008   10.0000
omega____ theta____ kappa____ phi______ frames
 160.6497   85.0000   73.8672     -     306

  3 omega   82.21  269.21   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   73.8672  -20.7898 187

  4 phi     87.46  264.60   1.0008   10.0000
omega____ theta____ kappa____ phi______ frames
 -46.7703  -35.0000   73.8672     -     177

  5 phi   -137.69  151.58   1.0009   30.0000
omega____ theta____ kappa____ phi______ frames
 111.1696  110.5000   73.8672     -     289

  6 omega  -15.16  119.84   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -37.0000   73.8672  114.2100 135

  7 omega   53.97  128.96   0.9998   10.0000
omega____ theta____ kappa____ phi______ frames
    -       83.0000   73.8672   -5.7905 75

  8 omega   53.21  154.20   0.9999   10.0000
omega____ theta____ kappa____ phi______ frames
    -       83.0000   73.8672 -110.7900 101

  9 omega   86.36  267.36   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   73.8672   19.2097 181

 10 omega  126.56  198.56   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       80.0000   73.8672   29.2103 72

 11 phi     82.54  328.77   1.0009   30.0000
omega____ theta____ kappa____ phi______ frames
 134.1596  105.0000   73.8672     -     246

 12 phi     22.13  317.36   1.0008   10.0000
omega____ theta____ kappa____ phi______ frames
  71.2396   90.0000   73.8672     -     295

 13 phi    -25.79  333.43   1.0006   30.0000
omega____ theta____ kappa____ phi______ frames
  84.2097  110.0000   73.8672     -     359

;
_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  0.097
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            61798
_diffrn_reflns_theta_full        69.761
_diffrn_reflns_theta_max         74.627
_diffrn_reflns_theta_min         2.985
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.718
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.50458
_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            'dark pink'
_exptl_crystal_density_diffrn    1.507
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             2992
_exptl_crystal_size_max          0.65
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.03
_refine_diff_density_max         1.20
_refine_diff_density_min         -0.61
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   0.9865
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     910
_refine_ls_number_reflns         12834
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0992
_refine_ls_R_factor_gt           0.0724
_refine_ls_shift/su_max          0.0004361
_refine_ls_shift/su_mean         0.0000343
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method= Modified Sheldrick 
 w=1/[\s^2^(F^2^) + ( 0.11P)^2^ +11.43P] 
 ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.2067
_refine_ls_wR_factor_gt          0.1884
_refine_ls_wR_factor_ref         0.2067
_reflns_limit_h_max              17
_reflns_limit_h_min              -17
_reflns_limit_k_max              27
_reflns_limit_k_min              0
_reflns_limit_l_max              24
_reflns_limit_l_min              0
_reflns_number_gt                9196
_reflns_number_total             12885
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   2.64
_oxford_diffrn_Wilson_scale      0.65
_oxford_refine_ls_r_factor_ref   0.0992
_oxford_refine_ls_scale          1.244(7)
_oxford_reflns_number_all        12834
_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_cell_volume        6448.5(3)
_cod_original_sg_symbol_H-M      'P 1 21/c 1 '
_cod_database_code               1520537
_iucr_refine_instruction_details_constraints
;
BLOCK SCALE X'S, U'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   (   8,X'S) H   (  81,X'S) 
RIDE C   (  11,X'S) H   ( 111,X'S) 
RIDE C   (  27,X'S) H   ( 271,X'S) 
RIDE C   (  28,X'S) H   ( 281,X'S) 
RIDE C   (  29,X'S) H   ( 291,X'S) 
RIDE C   (  32,X'S) H   ( 321,X'S) 
RIDE C   (  35,X'S) H   ( 351,X'S) 
RIDE C   (  51,X'S) H   ( 511,X'S) H   ( 512,X'S) 
RIDE C   (  52,X'S) H   ( 521,X'S) H   ( 522,X'S) 
RIDE C   (  53,X'S) H   ( 531,X'S) H   ( 532,X'S) 
RIDE C   (  54,X'S) H   ( 541,X'S) H   ( 542,X'S) 
RIDE C   (  55,X'S) H   ( 552,X'S) H   ( 551,X'S) 
RIDE C   (  56,X'S) H   ( 561,X'S) H   ( 562,X'S) 
RIDE C   (  57,X'S) H   ( 572,X'S) H   ( 571,X'S) 
RIDE C   (  58,X'S) H   ( 581,X'S) H   ( 583,X'S) H   ( 582,X'S) 
RIDE C   (  61,X'S) H   ( 611,X'S) H   ( 612,X'S) 
RIDE C   (  62,X'S) H   ( 622,X'S) H   ( 621,X'S) 
RIDE C   (  63,X'S) H   ( 631,X'S) H   ( 632,X'S) 
RIDE C   (  64,X'S) H   ( 641,X'S) H   ( 642,X'S) 
RIDE C   (  65,X'S) H   ( 651,X'S) H   ( 652,X'S) 
RIDE C   (  66,X'S) H   ( 661,X'S) H   ( 662,X'S) 
RIDE C   (  67,X'S) H   ( 672,X'S) H   ( 671,X'S) 
RIDE C   (  68,X'S) H   ( 681,X'S) H   ( 682,X'S) H   ( 683,X'S) 
RIDE C   (  71,X'S) H   ( 711,X'S) H   ( 712,X'S) H   ( 713,X'S) 
RIDE C   (  72,X'S) H   ( 721,X'S) H   ( 722,X'S) H   ( 723,X'S) 
RIDE C   (  81,X'S) H   ( 812,X'S) H   ( 811,X'S) H   ( 813,X'S) 
RIDE C   (  82,X'S) H   ( 822,X'S) H   ( 821,X'S) H   ( 823,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                                                                             
;