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_1543329
_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         'C38 H42 Br2 N4 S4'
_chemical_formula_sum            'C38 H42 Br2 N4 S4'
_chemical_formula_weight         842.81
_chemical_name_systematic
2,2'-(2,3-bis(5-octylthiophen-2-yl)quinoxaline-5,8-diyl)bis(5-bromothiazole)
_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                91.596(5)
_cell_angle_beta                 97.865(5)
_cell_angle_gamma                105.823(6)
_cell_formula_units_Z            2
_cell_length_a                   9.0551(6)
_cell_length_b                   10.0299(7)
_cell_length_c                   22.0044(12)
_cell_measurement_reflns_used    1990
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.8350
_cell_measurement_theta_min      3.3980
_cell_volume                     1900.2(2)
_computing_cell_refinement
;
Agilent Technologies, (2013), CrysAlisPro Software system, 
version 1.171. 37.31, Agilent Technologies UK Ltd, Oxford, UK
;
_computing_data_collection
;
Agilent Technologies, (2013), CrysAlisPro Software system, 
version 1.171.37.31, Agilent Technologies UK Ltd, Oxford, UK
;
_computing_data_reduction
;
Agilent Technologies, (2013), CrysAlisPro Software system, 
version 1.171. 37.31, 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 0.995
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_details
;
  1 omega    1.00   87.00   1.0000   70.0000
omega____ theta____ kappa____ phi______ frames
    -       25.5614 -131.0000  126.0000 86

  2 omega  -88.00   -1.00   1.0000   70.0000
omega____ theta____ kappa____ phi______ frames
    -      -27.1239  131.0000 -162.0000 87

  3 omega -103.00  -35.00   1.0000   70.0000
omega____ theta____ kappa____ phi______ frames
    -      -27.1239 -178.0000 -120.0000 68

  4 omega  -52.00   45.00   1.0000   70.0000
omega____ theta____ kappa____ phi______ frames
    -      -27.1239   39.0000 -178.8752 97

  5 omega -100.00   17.00   1.0000   70.0000
omega____ theta____ kappa____ phi______ frames
    -      -27.1239  -19.0000 -180.0000 117

  6 omega  -97.00  -79.00   1.0000   70.0000
omega____ theta____ kappa____ phi______ frames
    -      -27.1239  -77.0000   90.0000 18
;
_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  0.0821
_diffrn_reflns_av_unetI/netI     0.1882
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            21348
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.508
_diffrn_reflns_theta_min         3.230
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    2.386
_exptl_absorpt_correction_T_max  0.985
_exptl_absorpt_correction_T_min  0.544
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
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)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'translucent intense yellow'
_exptl_crystal_density_diffrn    1.473
_exptl_crystal_description       plate
_exptl_crystal_F_000             864
_exptl_crystal_size_max          0.727
_exptl_crystal_size_mid          0.628
_exptl_crystal_size_min          0.013
_refine_diff_density_max         0.785
_refine_diff_density_min         -0.772
_refine_diff_density_rms         0.113
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.999
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     485
_refine_ls_number_reflns         11488
_refine_ls_number_restraints     90
_refine_ls_restrained_S_all      1.008
_refine_ls_R_factor_all          0.2292
_refine_ls_R_factor_gt           0.0870
_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^)+(0.0832P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1758
_refine_ls_wR_factor_ref         0.2507
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4595
_reflns_number_total             11488
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6py00370b2.cif
_cod_data_source_block           fc67_4
_cod_depositor_comments
'Adding full bibliography for 1543328--1543330.cif.'
_cod_database_code               1543329
_shelxl_version_number           2013-4
_shelx_estimated_absorpt_t_max   0.970
_shelx_estimated_absorpt_t_min   0.276
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C24-C25 = C24-C25B = C35-C36 = C36-C37 = C37-C38 = C35-C36B = C36B-C37B =
 C37B-C38B
 1.5 with sigma of 0.02
 C35-C37B = C36B-C38B
 2.5 with sigma of 0.02
 C9-Br2 = C9-Br2B
 1.85 with sigma of 0.005
3. Uiso/Uaniso restraints and constraints
C35 \\sim C36B \\sim C36 \\sim C37 \\sim C37B \\sim C38B \\sim C38: within 1.7A
with sigma of 0.01 and sigma for terminal atoms of 0.02
C25 \\sim C25B: within 1.7A with sigma of 0.01 and sigma for terminal atoms of
0.02
Br2 \\sim Br2B: within 1.7A with sigma of 0.005 and sigma for terminal atoms of
0.01
Uanis(C25B) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
4. Others
 Sof(H24C)=Sof(H24D)=Sof(C25B)=Sof(H25D)=Sof(H25E)=Sof(H25F)=1-FVAR(1)
 Sof(H24A)=Sof(H24B)=Sof(C25)=Sof(H25A)=Sof(H25B)=Sof(H25C)=FVAR(1)
 Sof(H35C)=Sof(H35D)=Sof(C36B)=Sof(H36C)=Sof(H36D)=Sof(C37B)=Sof(H37C)=
 Sof(H37D)=Sof(C38B)=Sof(H38D)=Sof(H38E)=Sof(H38F)=1-FVAR(2)
 Sof(H35A)=Sof(H35B)=Sof(C36)=Sof(H36A)=Sof(H36B)=Sof(C37)=Sof(H37A)=Sof(H37B)=
 Sof(C38)=Sof(H38A)=Sof(H38B)=Sof(H38C)=FVAR(2)
 Sof(Br2B)=1-FVAR(3)
 Sof(Br2)=FVAR(3)
5.a Secondary CH2 refined with riding coordinates:
 C18(H18A,H18B), C19(H19A,H19B), C20(H20A,H20B), C21(H21A,H21B), C22(H22A,
 H22B), C23(H23A,H23B), C24(H24A,H24B), C24(H24C,H24D), C31(H31A,H31B),
 C32(H32A,H32B), C33(H33A,H33B), C34(H34A,H34B), C35(H35A,H35B), C35(H35C,H35D),
  C36(H36A,H36B), C36B(H36C,H36D), C37(H37A,H37B), C37B(H37C,H37D)
5.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C8(H8), C11(H11), C15(H15), C16(H16), C28(H28), C29(H29)
5.c Idealised Me refined as rotating group:
 C25(H25A,H25B,H25C), C25B(H25D,H25E,H25F), C38(H38A,H38B,H38C), C38B(H38D,
 H38E,H38F)
;
_olex2_submission_special_instructions 'No special instructions were received'