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_1520535
_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         'C41 H46 N4 S2'
_chemical_formula_sum            'C41 H46 N4 S2'
_chemical_formula_weight         658.97
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/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                 106.002(4)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   24.1082(9)
_cell_length_b                   18.1370(7)
_cell_length_c                   16.7624(7)
_cell_measurement_reflns_used    4470
_cell_measurement_temperature    150(1)
_cell_measurement_theta_max      27.4560
_cell_measurement_theta_min      3.2960
_cell_volume                     7045.4(5)
_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      150(1)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.872
_diffrn_measurement_details
;
  1 omega  -92.00  -39.00   1.0000   24.0000
omega____ theta____ kappa____ phi______ frames
    -      -25.3942  178.0000   60.0000 53

  2 omega -107.00   58.00   1.0000   24.0000
omega____ theta____ kappa____ phi______ frames
    -      -25.3942    0.0000    0.0000 165

  3 omega   56.00   95.00   1.0000   24.0000
omega____ theta____ kappa____ phi______ frames
    -       25.8629  178.0000 -180.0000 39

;
_diffrn_measurement_device       Serial
_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     0.71073
_diffrn_reflns_av_R_equivalents  0.031
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            14311
_diffrn_reflns_theta_full        26.353
_diffrn_reflns_theta_max         28.552
_diffrn_reflns_theta_min         3.107
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.187
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.81391
_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            yellow
_exptl_crystal_density_diffrn    1.242
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod
_exptl_crystal_F_000             2816
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.54
_refine_diff_density_min         -0.58
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   0.9999
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     470
_refine_ls_number_reflns         7816
_refine_ls_number_restraints     40
_refine_ls_R_factor_all          0.0855
_refine_ls_R_factor_gt           0.0613
_refine_ls_shift/su_max          0.0017657
_refine_ls_shift/su_mean         0.0000847
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method= Modified Sheldrick 
 w=1/[\s^2^(F^2^) + ( 0.04P)^2^ +18.72P] 
 ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1513
_refine_ls_wR_factor_gt          0.1366
_refine_ls_wR_factor_ref         0.1513
_reflns_limit_h_max              30
_reflns_limit_h_min              -30
_reflns_limit_k_max              24
_reflns_limit_k_min              0
_reflns_limit_l_max              21
_reflns_limit_l_min              0
_reflns_number_gt                5781
_reflns_number_total             7830
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   2.66
_oxford_diffrn_Wilson_scale      0.47
_oxford_refine_ls_r_factor_ref   0.0855
_oxford_refine_ls_scale          1.523(8)
_oxford_reflns_number_all        7816
_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      'C 1 2/c 1 '
_cod_database_code               1520535
_iucr_refine_instruction_details_constraints
;
BLOCK SCALE X'S, N(1,U'S) UNTIL C(36) 
CONT C(370, U'S, OCC) UNTIL C(411) 
EQUIV C(370, OCC), C(371, OCC), C(380, OCC), C(381, OCC), 
CONT C(390, OCC), C(391, OCC) 
CONT C(400, OCC), C(401, OCC), C(410, OCC), C(411, OCC) 
WEIGHT -1 C(370, OCC) C(380, OCC) C(390, OCC) C(400, OCC) 
CONT C(410, 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   (   9,X'S) H   (  91,X'S) 
RIDE C   (  12,X'S) H   ( 121,X'S) 
RIDE C   (  14,X'S) H   ( 141,X'S) 
RIDE C   (  15,X'S) H   ( 151,X'S) 
RIDE C   (  17,X'S) H   ( 171,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   (  26,X'S) H   ( 261,X'S) H   ( 262,X'S) 
RIDE C   (  27,X'S) H   ( 271,X'S) H   ( 272,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) 
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) H   ( 333,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   ( 370,X'S) H   (3701,X'S) H   (3702,X'S) 
RIDE C   ( 371,X'S) H   (3711,X'S) H   (3712,X'S) 
RIDE C   ( 380,X'S) H   (3801,X'S) H   (3802,X'S) 
RIDE C   ( 381,X'S) H   (3811,X'S) H   (3812,X'S) 
RIDE C   ( 390,X'S) H   (3901,X'S) H   (3902,X'S) 
RIDE C   ( 391,X'S) H   (3911,X'S) H   (3912,X'S) 
RIDE C   ( 400,X'S) H   (4001,X'S) H   (4002,X'S) 
RIDE C   ( 401,X'S) H   (4011,X'S) H   (4012,X'S) 
RIDE C   ( 410,X'S) H   (4101,X'S) H   (4102,X'S) H   (4103,X'S) 
RIDE C   ( 411,X'S) H   (4111,X'S) H   (4112,X'S) H   (4113,X'S) 
END                                                                             
;
_iucr_refine_instruction_details_restraints
;
DIST 0.0, 0.01 = MEAN C(36) TO C(370) , C(36) TO C(371) 
DIST 0.0, 0.01 = MEAN C(370) TO C(380) , C(371) TO C(381) 
DIST 0.0, 0.01 = MEAN C(380) TO C(390) , C(381) TO C(391) 
DIST 0.0, 0.01 = MEAN C(390) TO C(400) , C(391) TO C(401) 
DIST 0.0, 0.01 = MEAN C(400) TO C(410) , C(401) TO C(411) 
REM 
U(IJ) 0.0, 0.02 = C(370) TO C(371) 
U(IJ) 0.0, 0.02 = C(380) TO C(381) 
U(IJ) 0.0, 0.02 = C(390) TO C(391) 
U(IJ) 0.0, 0.02 = C(400) TO C(401) 
U(IJ) 0.0, 0.02 = C(410) TO C(411) 
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
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