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_1520536
_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 H64 B2 N4 S2'
_chemical_formula_sum            'C65 H64 B2 N4 S2'
_chemical_formula_weight         987.00
_space_group_IT_number           88
_symmetry_cell_setting           tetragonal
_symmetry_space_group_name_Hall  '-I 4ad'
_symmetry_space_group_name_H-M   'I 41/a :2'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     other
_audit_update_record
;
2015-02-23 deposited with the CCDC.
2015-06-12 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            16
_cell_length_a                   41.5940(9)
_cell_length_b                   41.5940(9)
_cell_length_c                   13.1413(6)
_cell_measurement_reflns_used    7633
_cell_measurement_temperature    149.99(19)
_cell_measurement_theta_max      26.5010
_cell_measurement_theta_min      3.4590
_cell_volume                     22735.2(12)
_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    'Superflip (Palatinus & Chapuis, 2007)'
_diffrn_ambient_temperature      149.99(19)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details
;
  1 omega  -49.00   44.00   0.7500   50.0000
omega____ theta____ kappa____ phi______ frames
    -       21.3360  -57.0000 -120.0000 124

  2 omega   52.00  101.50   0.7500   50.0000
omega____ theta____ kappa____ phi______ frames
    -       21.3360 -178.0000  -90.0000 66

  3 omega   -2.00   89.50   0.7500   50.0000
omega____ theta____ kappa____ phi______ frames
    -       21.3360   57.0000   30.0000 122

;
_diffrn_measurement_device_type  'SuperNova, Single source at offset), Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_source         'SuperNova (Mo) X-ray Source'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.038
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_k_max       43
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            6933
_diffrn_reflns_theta_full        21.965
_diffrn_reflns_theta_max         21.965
_diffrn_reflns_theta_min         3.059
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.137
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.47428
_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            red
_exptl_crystal_density_diffrn    1.153
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             8384
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_platon_squeeze_details
;
;
_refine_diff_density_max         0.68
_refine_diff_density_min         -0.47
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   0.9870
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     723
_refine_ls_number_reflns         6906
_refine_ls_number_restraints     77
_refine_ls_R_factor_all          0.0778
_refine_ls_R_factor_gt           0.0600
_refine_ls_shift/su_max          0.0032448
_refine_ls_shift/su_mean         0.0001514
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method= Modified Sheldrick 
 w=1/[\s^2^(F^2^) + ( 0.07P)^2^ +85.99P] 
 ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1619
_refine_ls_wR_factor_gt          0.1520
_refine_ls_wR_factor_ref         0.1619
_reflns_limit_h_max              30
_reflns_limit_h_min              -30
_reflns_limit_k_max              43
_reflns_limit_k_min              0
_reflns_limit_l_max              13
_reflns_limit_l_min              0
_reflns_number_gt                5398
_reflns_number_total             6933
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   2.70
_oxford_diffrn_Wilson_scale      191.24
_oxford_refine_ls_r_factor_ref   0.0778
_oxford_refine_ls_scale          0.08663(3)
_oxford_reflns_number_all        6906
_oxford_reflns_threshold_expression_ref I>-3.0\s(I)
_cod_data_source_file            c5sc01800e2.cif
_cod_data_source_block           1
_cod_depositor_comments
;
The following automatic conversions were performed:

'_atom_sites_solution_primary' value 'Other' changed to 'other'
according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 3271 2015-04-21 07:52:19Z andrius 

 Adding full bibliography for 1520535--1520540.cif.
;
_cod_original_sg_symbol_H-M      'I 41/a '
_cod_database_code               1520536
_iucr_refine_instruction_details_constraints
;
BLOCK SCALE X'S, B(1, U'S) UNTIL C(68) 
CONT C(550, U'S, OCC) UNTIL C(661) 
EQUIV C(550, OCC) C(551, OCC) C(560, OCC) C(561, OCC) C(570, OCC) 
CONT C(571, OCC) 
WEIGHT -1 C(550, OCC) C(560, OCC) C(570, OCC) 
EQUIV C(630, OCC) C(631, OCC) C(640, OCC) C(641, OCC) 
CONT C(650, OCC) C(651, OCC) C(660, OCC) C(661, OCC) 
WEIGHT -1 C(630, OCC) C(640, OCC) 
CONT C(650, OCC) C(660, OCC) 
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   (  14,X'S) H   ( 141,X'S) 
RIDE C   (  15,X'S) H   ( 151,X'S) 
RIDE C   (  16,X'S) H   ( 161,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   (  22,X'S) H   ( 221,X'S) 
RIDE C   (  23,X'S) H   ( 231,X'S) 
RIDE C   (  24,X'S) H   ( 241,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   (  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) 
RIDE C   (  44,X'S) H   ( 441,X'S) 
RIDE C   (  45,X'S) H   ( 451,X'S) 
RIDE C   (  46,X'S) H   ( 461,X'S) 
RIDE C   (  47,X'S) H   ( 471,X'S) 
RIDE C   (  48,X'S) H   ( 481,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   (  58,X'S) H   ( 581,X'S) H   ( 582,X'S) H   ( 583,X'S) 
RIDE C   (  61,X'S) H   ( 611,X'S) H   ( 612,X'S) 
RIDE C   (  62,X'S) H   ( 621,X'S) H   ( 622,X'S) 
RIDE C   (  67,X'S) H   (671,X'S) H   (672,X'S) 
RIDE C   (  68,X'S) H   ( 681,X'S) H   ( 682,X'S) H   ( 683,X'S) 
RIDE C   ( 550,X'S) H   (5501,X'S) H   (5502,X'S) 
RIDE C   ( 551,X'S) H   (5511,X'S) H   (5512,X'S) 
RIDE C   ( 560,X'S) H   (5601,X'S) H   (5602,X'S) 
RIDE C   ( 561,X'S) H   (5611,X'S) H   (5612,X'S) 
RIDE C   ( 570,X'S) H   (5701,X'S) H   (5702,X'S) 
RIDE C   ( 571,X'S) H   (5711,X'S) H   (5712,X'S) 
RIDE C   ( 630,X'S) H   (6301,X'S) H   (6302,X'S) 
RIDE C   ( 631,X'S) H   (6311,X'S) H   (6312,X'S) 
RIDE C   ( 640,X'S) H   (6401,X'S) H   (6402,X'S) 
RIDE C   ( 641,X'S) H   (6411,X'S) H   (6412,X'S) 
RIDE C   ( 650,X'S) H   (6501,X'S) H   (6502,X'S) 
RIDE C   ( 651,X'S) H   (6511,X'S) H   (6512,X'S) 
RIDE C   ( 660,X'S) H   (6601,X'S) H   (6602,X'S) 
RIDE C   ( 661,X'S) H   (6611,X'S) H   (6612,X'S) 
END                                                                             
;
_iucr_refine_instruction_details_restraints
;
REM DIST 1.5, 0.03 = C(550) TO C(560) 
DIST 1.5, 0.03 = C(551) TO C(561) 
REM DIST 1.53, 0.01 = C(560) TO C(570) 
DIST 1.5, 0.03 = C(561) TO C(571) 
REM DIST 1.5, 0.05 = C(570) TO C(58) 
REM DIST 1.5, 0.03 = C(571) TO C(58) 
REM DIST 1.53, 0.05 = C(62) TO C(630) 
REM DIST 1.53, 0.05 = C(630) TO C(640) 
DIST 1.53, 0.05 = C(640) TO C(650) 
DIST 1.53, 0.01 = C(650) TO C(660) 
DIST 1.53, 0.01 = C(660) TO C(67) 
DIST 1.53, 0.02 = C(67) TO C(68) 
DIST 1.53, 0.05 = C(62) TO C(631) 
REM DIST 1.53, 0.05 = C(631) TO C(641) 
DIST 1.53, 0.05 = C(641) TO C(651) 
DIST 1.53, 0.01 = C(651) TO C(661) 
DIST 1.53, 0.01 = C(661) TO C(67) 
DIST 1.53, 0.05 = C(67) TO C(68) 
REM ANGLE 117.0, 0.4 = C(550) TO C(560) TO C(570) 
REM ANGLE 117.0, 0.4 = C(551) TO C(561) TO C(571) 
REM ANGLE 117.0, 0.4 = C(560) TO C(570) TO C(58) 
U(IJ) 0.0, 0.01 = C(54) TO C(550) 
U(IJ) 0.0, 0.01 = C(54) TO C(551) 
U(IJ) 0.0, 0.01 = C(551) TO C(550) 
U(IJ) 0.0, 0.01 = C(561) TO C(560) 
U(IJ) 0.0, 0.01 = C(550) TO C(560) 
U(IJ) 0.0, 0.01 = C(551) TO C(561) 
U(IJ) 0.0, 0.01 = C(571) TO C(570) 
U(IJ) 0.0, 0.01 = C(630) TO C(631) 
U(IJ) 0.0, 0.01 = C(640) TO C(641) 
U(IJ) 0.0, 0.01 = C(650) TO C(660) 
U(IJ) 0.0, 0.02 = C(651) TO C(661) 
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
;