A bacteriochlorin-diketopyrrolopyrrole triad as a donor for solution-processed bulk heterojunction organic solar cells
Ponsot, Flavien; Bucher, Léo; Desbois, Nicolas; Rousselin, Yoann; Mondal, Pritam; Devillers, Charles H.; Romieu, Anthony; Gros, Claude P.; Singhal, Rahul; Sharma, Ganesh D.; Journal of Materials Chemistry C 7 (2019) 9655–; doi:10.1039/C9TC02724F

data_7237897
_publ_section_title
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 A bacteriochlorin-diketopyrrolopyrrole triad as a donor for
 solution-processed bulk heterojunction organic solar cells
;
_journal_issue                   31
_journal_name_full               'Journal of Materials Chemistry C'
_journal_page_first              9655
_journal_paper_doi               10.1039/C9TC02724F
_journal_volume                  7
_journal_year                    2019
_chemical_formula_moiety         'C25 H26 Br2 N4 O'
_chemical_formula_sum            'C25 H26 Br2 N4 O'
_chemical_formula_weight         558.32
_chemical_name_systematic
3,13-Dibromo-5-methoxy-8,8,18,18-tetramethylbacteriochlorin
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-I 2ya'
_space_group_name_H-M_alt        'I 1 2/a 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2019-03-27
_audit_creation_method
;
Olex2 1.2
(compiled May 18 2018 14:05:52 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-04-15 deposited with the CCDC.	2019-07-16 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.947(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   18.3753(10)
_cell_length_b                   5.8406(3)
_cell_length_c                   21.3396(19)
_cell_measurement_reflns_used    7598
_cell_measurement_temperature    100.0(1)
_cell_measurement_theta_max      27.40
_cell_measurement_theta_min      2.85
_cell_volume                     2287.2(3)
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2016)'
_computing_data_collection       'APEX3 (Bruker, 2015)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2016)'
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100.0(1)
_diffrn_detector                 CMOS
_diffrn_detector_area_resol_mean '1024 x 1024'
_diffrn_detector_type            'Photon 100'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       '\k-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Venture (Mo)'
_diffrn_measurement_method       '\f and \w scans''
_diffrn_radiation_collimation    '0.6 mm'
_diffrn_radiation_monochromator  'TRIUMPH curved crystal'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0372
_diffrn_reflns_av_unetI/netI     0.0290
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            15003
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.552
_diffrn_reflns_theta_min         2.854
_diffrn_source                   'X-ray tube'
_diffrn_source_target            Mo
_diffrn_source_type              'Siemens KFF Mo 2K-90C'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.570
_exptl_absorpt_correction_T_max  0.4915
_exptl_absorpt_correction_T_min  0.3788
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016) was used for absorption correction.
wR2(int) was 0.0847 before and 0.0528 after correction.
The Ratio of minimum to maximum transmission is 0.7707.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear dark violet'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    violet
_exptl_crystal_density_diffrn    1.621
_exptl_crystal_description       prism
_exptl_crystal_F_000             1128
_exptl_crystal_recrystallization_method
'The material was recrystallised from chloroform by slow evaporation'
_exptl_crystal_size_max          0.418
_exptl_crystal_size_mid          0.196
_exptl_crystal_size_min          0.144
_refine_diff_density_max         0.561
_refine_diff_density_min         -0.558
_refine_diff_density_rms         0.075
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     160
_refine_ls_number_reflns         2629
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.015
_refine_ls_R_factor_all          0.0423
_refine_ls_R_factor_gt           0.0302
_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^)+(0.0311P)^2^+4.9290P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0682
_refine_ls_wR_factor_ref         0.0729
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2165
_reflns_number_total             2629
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9tc02724f2.cif
_cod_data_source_block           diBr-BC
_cod_database_code               7237897
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.627
_shelx_estimated_absorpt_t_min   0.317
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Fixed Sof: H6(0.5) O1(0.5) C7(0.5) H7A(0.5) H7B(0.5) H7C(0.5)
3.a Fixed occupancy and ADP/Uiso:
 H2
3.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B)
3.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C10(H10), C6(H6)
3.d Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C12(H12A,H12B,H12C), C7(H7A,H7B,H7C)
;
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method
'The crystal was mounted on a MITIGEN holder oil'
_olex2_submission_special_instructions 'No special instructions were received'