Synthesis, optoelectronic properties and photovoltaic performances of wide band-gap copolymers based on dibenzosilole and quinoxaline units, rivals to P3HT
Caffy, F.; Delbosc, N.; Chávez, P.; Lévêque, P.; Faure-Vincent, J.; Travers, J.-P.; Djurado, D.; Pécaut, J.; Grévin, B.; Lemaitre, N.; Leclerc, N.; Demadrille, R.; Polym. Chem. 7 (2016) 4160–; doi:10.1039/C6PY00370B

data_1543330
_publ_section_title
;
 Synthesis, optoelectronic properties and photovoltaic performances of
 wide band-gap copolymers based on dibenzosilole and quinoxaline units,
 rivals to P3HT
;
_journal_issue                   25
_journal_name_full               'Polym. Chem.'
_journal_page_first              4160
_journal_paper_doi               10.1039/C6PY00370B
_journal_volume                  7
_journal_year                    2016
_chemical_formula_moiety         'C40 H42 Br2 F2 N2 S4'
_chemical_formula_sum            'C40 H42 Br2 F2 N2 S4'
_chemical_formula_weight         876.81
_chemical_name_systematic
5,8-bis(5-bromothiophen-2-yl)-6,7-difluoro-2,3-bis(5-octylthiophen-2-yl)quinoxaline
_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
_audit_creation_date             2015-11-10
_audit_creation_method
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_audit_update_record
;
2016-03-01 deposited with the CCDC.
2016-05-05 downloaded from the CCDC.
;
_cell_angle_alpha                112.675(6)
_cell_angle_beta                 100.139(5)
_cell_angle_gamma                92.575(5)
_cell_formula_units_Z            6
_cell_length_a                   16.7687(11)
_cell_length_b                   18.2589(12)
_cell_length_c                   20.6070(12)
_cell_measurement_reflns_used    2440
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      28.5480
_cell_measurement_theta_min      3.4210
_cell_volume                     5686.5(7)
_computing_cell_refinement
;
Agilent Technologies, (2013), CrysAlisPro Software system, 
version 1.171. 36.28, Agilent Technologies UK Ltd, Oxford, UK
;
_computing_data_collection
;
Agilent Technologies, (2013), CrysAlisPro Software system, 
version 1.171.36.28, Agilent Technologies UK Ltd, Oxford, UK
;
_computing_data_reduction
;
Agilent Technologies, (2013), CrysAlisPro Software system, 
version 1.171. 36.28, Agilent Technologies UK Ltd, Oxford, UK
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement
;
OLEX2: a complete structure solution, refinement and analysis program 
(O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and 
H. Puschmann. J. Appl. Cryst. 2009, 42, 339-34).
;
_computing_structure_solution
;
SUPERFLIP program (Palatinus, L. & Chapuis, G. J. Appl. Cryst., 2007,
 40, 786-790)
;
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 15.9653
_diffrn_measured_fraction_theta_full 0.972
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measurement_details
;
  1 omega  -49.00   42.00   1.0000  160.0000
omega____ theta____ kappa____ phi______ frames
    -      -27.1239   57.0000  150.0000 91

  2 omega  -97.00    3.00   1.0000  160.0000
omega____ theta____ kappa____ phi______ frames
    -      -27.1239  -77.0000 -180.0000 100

  3 omega  -97.00    3.00   1.0000  160.0000
omega____ theta____ kappa____ phi______ frames
    -      -27.1239  -77.0000  -90.0000 100

  4 omega  -57.00   16.00   1.0000  160.0000
omega____ theta____ kappa____ phi______ frames
    -      -27.1239   77.0000   30.0000 73
;
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0686
_diffrn_reflns_av_unetI/netI     0.1577
_diffrn_reflns_Laue_measured_fraction_full 0.972
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            38407
_diffrn_reflns_point_group_measured_fraction_full 0.972
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_min         3.215
_exptl_absorpt_coefficient_mu    2.401
_exptl_absorpt_correction_T_max  0.914
_exptl_absorpt_correction_T_min  0.536
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Analytical numeric absorption correction using a multifaceted crystal
            model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_exptl_crystal_colour            'translucent intense orange'
_exptl_crystal_density_diffrn    1.536
_exptl_crystal_description       needle
_exptl_crystal_F_000             2688
_exptl_crystal_size_max          0.457
_exptl_crystal_size_mid          0.057
_exptl_crystal_size_min          0.043
_refine_diff_density_max         1.323
_refine_diff_density_min         -0.828
_refine_diff_density_rms         0.105
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.973
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1357
_refine_ls_number_reflns         22546
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.973
_refine_ls_R_factor_all          0.1857
_refine_ls_R_factor_gt           0.0742
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0343P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1218
_refine_ls_wR_factor_ref         0.1659
_reflns_Friedel_coverage         0.000
_reflns_number_gt                9934
_reflns_number_total             22546
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6py00370b2.cif
_cod_data_source_block           fl57
_cod_depositor_comments
'Adding full bibliography for 1543328--1543330.cif.'
_cod_database_code               1543330
_shelxl_version_number           2013-4
_shelx_estimated_absorpt_t_max   0.904
_shelx_estimated_absorpt_t_min   0.407
_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.a Secondary CH2 refined with riding coordinates:
 C21(H21A,H21B), C22(H22A,H22B), C23(H23A,H23B), C24(H24A,H24B), C25(H25A,
 H25B), C26(H26A,H26B), C27(H27A,H27B), C33(H33A,H33B), C34(H34A,H34B),
 C35(H35A,H35B), C36(H36A,H36B), C37(H37A,H37B), C38(H38A,H38B), C39(H39A,H39B),
  C61(H61A,H61B), C62(H62A,H62B), C63(H63A,H63B), C64(H64A,H64B), C65(H65A,
 H65B), C66(H66A,H66B), C67(H67A,H67B), C73(H73A,H73B), C74(H74A,H74B),
 C75(H75A,H75B), C76(H76A,H76B), C77(H77A,H77B), C78(H78A,H78B), C79(H79A,H79B),
  C101(H10A,H10B), C102(H10C,H10D), C103(H10E,H10F), C104(H10G,H10H), C105(H10I,
 H10J), C106(H10K,H10L), C107(H10M,H10N), C113(H11A,H11B), C114(H11C,H11D),
 C115(H11E,H11F), C116(H11G,H11H), C117(H11I,H11J), C118(H11K,H11L), C119(H11M,
 H11N)
2.b Aromatic/amide H refined with riding coordinates:
 C10(H10), C11(H11), C14(H14), C15(H15), C18(H18), C19(H19), C30(H30),
 C31(H31), C50(H50), C51(H51), C54(H54), C55(H55), C58(H58), C59(H59), C70(H70),
  C71(H71), C90(H90), C91(H91), C94(H94), C95(H95), C98(H98), C99(H99),
 C110(H110), C111(H111)
2.c Idealised Me refined as rotating group:
 C28(H28A,H28B,H28C), C40(H40A,H40B,H40C), C68(H68A,H68B,H68C), C80(H80A,H80B,
 H80C), C108(H10O,H10P,H10Q), C120(H12A,H12B,H12C)
;
_olex2_submission_special_instructions 'No special instructions were received'