Borylated Arylamine‒Benzothiadiazole Donor‒Acceptor Materials as Low-LUMO, Low-Band-Gap Chromophores
Crossley, Daniel L.; Goh, Rosanne; Cid, Jessica; Vitorica-Yrezabal, Inigo; Turner, Michael L.; Ingleson, Michael J.; Organometallics  (2017) –; doi:10.1021/acs.organomet.7b00188

data_4087267
_publ_section_title
;
 Borylated Arylamine--Benzothiadiazole Donor--Acceptor Materials as
 Low-LUMO, Low-Band-Gap Chromophores
;
_journal_name_full               Organometallics
_journal_paper_doi               10.1021/acs.organomet.7b00188
_journal_year                    2017
_chemical_formula_moiety         'C54 H39 B N4 S, 0.25(C6 H14)'
_chemical_formula_sum            'C55.88 H43.38 B N4 S'
_chemical_formula_weight         813.69
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2017-01-18
_audit_creation_method
;
Olex2 1.2
(compiled 2017.01.04 svn.r3372 for OlexSys, GUI svn.r5292)
;
_cell_angle_alpha                107.025(4)
_cell_angle_beta                 97.494(4)
_cell_angle_gamma                93.238(4)
_cell_formula_units_Z            4
_cell_length_a                   10.9377(5)
_cell_length_b                   19.7172(8)
_cell_length_c                   20.4051(11)
_cell_measurement_reflns_used    12637
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.8930
_cell_measurement_theta_min      1.8210
_cell_volume                     4150.9(4)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_diffrn_ambient_temperature      100
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.978
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_details
;
  1 omega  -60.00  115.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       30.0000    0.0000    0.0000 175

  2 omega  -60.00   60.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       30.0000  -50.0000    0.0000 120

  3 omega  -60.00   60.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       30.0000  -50.0000  120.0000 120

  4 omega  -60.00   60.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       30.0000  -50.0000  240.0000 120
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type
'dtrek-CrysAlisPro-abstract goniometer imported rigaku-d*trek images'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0128381000
_diffrn_orient_matrix_UB_12      -0.0347908000
_diffrn_orient_matrix_UB_13      -0.0129690000
_diffrn_orient_matrix_UB_21      -0.0577302000
_diffrn_orient_matrix_UB_22      -0.0117575000
_diffrn_orient_matrix_UB_23      0.0047648000
_diffrn_orient_matrix_UB_31      -0.0240562000
_diffrn_orient_matrix_UB_32      -0.0000832000
_diffrn_orient_matrix_UB_33      -0.0329553000
_diffrn_radiation_monochromator  synchrotron
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.6889
_diffrn_reflns_av_R_equivalents  0.0569
_diffrn_reflns_av_unetI/netI     0.0773
_diffrn_reflns_Laue_measured_fraction_full 0.978
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            34898
_diffrn_reflns_point_group_measured_fraction_full 0.978
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_theta_full        24.415
_diffrn_reflns_theta_max         24.519
_diffrn_reflns_theta_min         1.829
_diffrn_source                   synchrotron
_exptl_absorpt_coefficient_mu    0.113
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.90846
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear bluish blue'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   bluish
_exptl_crystal_colour_primary    blue
_exptl_crystal_density_diffrn    1.302
_exptl_crystal_description       needle
_exptl_crystal_F_000             1710
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.788
_refine_diff_density_min         -0.545
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1118
_refine_ls_number_reflns         14866
_refine_ls_number_restraints     45
_refine_ls_restrained_S_all      6.634
_refine_ls_R_factor_all          0.1007
_refine_ls_R_factor_gt           0.0578
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0656P)^2^+1.0204P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1320
_refine_ls_wR_factor_ref         0.1512
_reflns_Friedel_coverage         0.000
_reflns_number_gt                9707
_reflns_number_total             14866
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            om7b00188_si_002.cif
_cod_data_source_block           dlc302
_cod_database_code               4087267
_shelxl_version_number           2014/6
_reflns_odcompleteness_completeness 83.97
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     31.80
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C0AA-C2AA
 2.4 with sigma of 0.02
 C4AA-C1AA
 2.4 with sigma of 0.02
 C2AA-C3AA
 2.4 with sigma of 0.02
 C9AA-C7AA = C8AA-C7AA = C8AA-C8AA
 1.54 with sigma of 0.002
 C8AA-C9AA
 2.4 with sigma of 0.02
 C7AA-C8AA
 2.4 with sigma of 0.02
 C8AA-C7AA
 2.4 with sigma of 0.02
 C9AA-C8AA
 2.4 with sigma of 0.02
 C8AA_$1-C8AA
 1.54 with sigma of 0.002
 C6AA-C0AA = C4AA-C0AA = C4AA-C2AA = C2AA-C1AA = C3AA-C1AA
 1.54 with sigma of 0.002
 C4AA-C6AA
 2.4 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
C8AA \\sim C9AA \\sim C7AA: within 2A with sigma of 0.002 and sigma for
terminal atoms of 0.004
C2AA \\sim C1AA \\sim C3AA \\sim C4AA \\sim C0AA \\sim C6AA: within 2A with
sigma of 0.002 and sigma for terminal atoms of 0.004
4. Others
 Sof(C9AA)=Sof(H9AA)=Sof(H9AB)=Sof(H9AC)=Sof(C7AA)=Sof(H7AA)=Sof(H7AB)=
 Sof(C8AA)=Sof(H8AA)=Sof(H8AB)=1-FVAR(1)
 Sof(C2AA)=Sof(H2AA)=Sof(H2AB)=Sof(C1AA)=Sof(H1AA)=Sof(H1AB)=Sof(C3AA)=
 Sof(H3AA)=Sof(H3AB)=Sof(H3AC)=Sof(C4AA)=Sof(H4AA)=Sof(H4AB)=Sof(C0AA)=
 Sof(H0AA)=Sof(H0AB)=Sof(C6AA)=Sof(H6AA)=Sof(H6AB)=Sof(H6AC)=0.5*FVAR(2)
5.a Secondary CH2 refined with riding coordinates:
 C2AA(H2AA,H2AB), C1AA(H1AA,H1AB), C4AA(H4AA,H4AB), C0AA(H0AA,H0AB), C7AA(H7AA,
 H7AB), C8AA(H8AA,H8AB)
5.b Me refined with riding coordinates:
 C3AA(H3AA,H3AB,H3AC), C9AA(H9AA,H9AB,H9AC), C6AA(H6AA,H6AB,H6AC)
5.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C9(H9), C39(H39), C48(H48), C24(H24), C38(H38), C29(H29), C5(H5),
 C42(H42), C52(H52), C26(H26), C54(H54), C30(H30), C28(H28), C53(H53), C32(H32),
  C49(H49), C51(H51), C36(H36), C23(H23), C43(H43), C27(H27), C35(H35),
 C12(H12), C46(H46), C18(H18), C50(H50), C20(H20), C13(H13), C33(H33), C19(H19),
  C16(H16), C44(H44), C34(H34), C21(H21), C22(H22), C15(H15), C14(H14),
 C45(H45), C63(H63), C92(H92), C86(H86), C93(H93), C59(H59), C58(H58), C78(H78),
  C77(H77), C90(H90), C87(H87), C107(H107), C88(H88), C108(H108), C104(H104),
 C102(H102), C72(H72), C80(H80), C96(H96), C89(H89), C106(H106), C105(H105),
 C66(H66), C84(H84), C70(H70), C103(H103), C100(H100), C99(H99), C67(H67),
 C83(H83), C69(H69), C82(H82), C68(H68), C73(H73), C97(H97), C81(H81), C98(H98),
  C76(H76), C74(H74), C75(H75)
;
_shelx_res_checksum              28316
_shelx_hkl_checksum              11418
_olex2_submission_special_instructions 'No special instructions were received'