Intermediate-Sized Conjugated Donor Molecules for Organic Solar Cells: Comparison of Benzodithiophene and Benzobisthiazole-Based Cores
Zhang, Siyuan; Zhang, Junxiang; Abdelsamie, Maged; Shi, Qinqin; Zhang, Yadong; Parker, Timothy C.; Jucov, Evgheni V.; Timofeeva, Tatiana V.; Amassian, Aram; Bazan, Guillermo C.; Blakey, Simon B.; Barlow, Stephen; Marder, Seth R.; Chemistry of Materials 29 (2017) 7880–; doi:10.1021/acs.chemmater.7b02665

data_4002842
_publ_section_title
;
 Intermediate-Sized Conjugated Donor Molecules for Organic Solar Cells:
 Comparison of Benzodithiophene and Benzobisthiazole-Based Cores
;
_journal_issue                   18
_journal_name_full               'Chemistry of Materials'
_journal_page_first              7880
_journal_paper_doi               10.1021/acs.chemmater.7b02665
_journal_volume                  29
_journal_year                    2017
_chemical_formula_moiety         'C16 H18 N S2'
_chemical_formula_sum            'C16 H20 N S2'
_chemical_formula_weight         290.45
_chemical_name_systematic
;
 4,8-bis(5-(2-ethylhexyl)thiophen-2-yl)-benzo[1,2-d:4,5-d']bis(thiazole) 
;
_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
_atom_sites_solution_secondary   difmap
_audit_creation_date             2016-03-14
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_cell_angle_alpha                94.287(5)
_cell_angle_beta                 100.125(5)
_cell_angle_gamma                106.893(5)
_cell_formula_units_Z            2
_cell_length_a                   6.213(2)
_cell_length_b                   9.183(3)
_cell_length_c                   14.383(5)
_cell_measurement_reflns_used    4993
_cell_measurement_temperature    273.1
_cell_measurement_theta_max      31.35
_cell_measurement_theta_min      2.34
_cell_volume                     766.0(4)
_computing_cell_refinement       'SAINT v8.27A (Bruker, 2012)'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'SAINT v8.27A (Bruker, 2012)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_diffrn_ambient_temperature      273.1
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0351
_diffrn_reflns_av_unetI/netI     0.0326
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            8767
_diffrn_reflns_theta_full        26.02
_diffrn_reflns_theta_max         26.02
_diffrn_reflns_theta_min         2.34
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.334
_exptl_absorpt_correction_T_max  0.7464
_exptl_absorpt_correction_T_min  0.6599
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2012/1 (Bruker,2012) was used for absorption correction. wR2(int) was 0.0729 before and 0.0492 after correction. The Ratio of minimum to maximum transmission is 0.8841. The \l/2 correction factor is 0.0015.'
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.259
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             310
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.03
_refine_diff_density_max         1.072
_refine_diff_density_min         -0.317
_refine_diff_density_rms         0.064
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         3022
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.003
_refine_ls_R_factor_all          0.0683
_refine_ls_R_factor_gt           0.0603
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1023P)^2^+0.8276P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1759
_refine_ls_wR_factor_ref         0.1847
_reflns_number_gt                2599
_reflns_number_total             3022
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cm7b02665_si_001.cif
_cod_data_source_block           jz-7
_cod_depositor_comments          'Adding full bibliography for 4002842.cif.'
_cod_original_cell_volume        766.1(5)
_cod_database_code               4002842
_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 Ternary CH refined with riding coordinates:
 C10(H10)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C12(H12A,H12B), C15(H15A,H15B)
2.c Me refined with riding coordinates:
 C14(H14A,H14B,H14C), C16(H16A,H16B,H16C)
2.d Aromatic/amide H refined with riding coordinates:
 C1(H1), C6(H6), C7(H7), C11(H11), C13(H13)
;
_olex2_submission_special_instructions 'No special instructions were received'