Boron–nitrogen substituted dihydroindeno[1,2-b]fluorene derivatives as acceptors in organic solar cells
Morgan, Matthew M.; Nazari, Maryam; Pickl, Thomas; Rautiainen, J. Mikko; Tuononen, Heikki M.; Piers, Warren E.; Welch, Gregory C.; Gelfand, Benjamin S.; Chemical Communications  (2019) –; doi:10.1039/C9CC05103A

data_7124075
_publ_section_title
;
 Boron--nitrogen substituted dihydroindeno[1,2-b]fluorene derivatives as
 acceptors in organic solar cells
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/C9CC05103A
_journal_year                    2019
_chemical_formula_moiety         'C24 H17 B F6 N'
_chemical_formula_sum            'C24 H17 B F6 N'
_chemical_formula_weight         444.19
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-03-07
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-06-28 deposited with the CCDC.    2019-08-28 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90.631(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.0824(4)
_cell_length_b                   22.2704(10)
_cell_length_c                   10.3537(4)
_cell_measurement_reflns_used    9864
_cell_measurement_temperature    173
_cell_measurement_theta_max      72.118
_cell_measurement_theta_min      3.970
_cell_volume                     2094.10(15)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_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      173
_diffrn_measured_fraction_theta_full 0.954
_diffrn_measured_fraction_theta_max 0.953
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0627
_diffrn_reflns_av_unetI/netI     0.0580
_diffrn_reflns_Laue_measured_fraction_full 0.954
_diffrn_reflns_Laue_measured_fraction_max 0.953
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            15951
_diffrn_reflns_point_group_measured_fraction_full 0.954
_diffrn_reflns_point_group_measured_fraction_max 0.953
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.245
_diffrn_reflns_theta_min         1.984
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.026
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.6602
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0878 before and 0.0713 after correction. The Ratio of minimum to maximum transmission is 0.8761. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.409
_exptl_crystal_description       plate
_exptl_crystal_F_000             908
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.271
_refine_diff_density_min         -0.440
_refine_diff_density_rms         0.074
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.120
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     293
_refine_ls_number_reflns         3653
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.120
_refine_ls_R_factor_all          0.0874
_refine_ls_R_factor_gt           0.0787
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1589P)^2^+0.4446P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2218
_refine_ls_wR_factor_ref         0.2292
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3287
_reflns_number_total             3653
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9cc05103a2.cif
_cod_data_source_block           83
_cod_database_code               7124075
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.904
_shelx_estimated_absorpt_t_min   0.821
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.742(3)
 0.258(3)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3.a Aromatic/amide H refined with riding coordinates:
 C5(H5), C8(H8), C1(H1), C7(H7), C17(H17), C15(H15), C23(H23), C21(H21)
3.b Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C11(H11A,H11B,H11C), C9(H9A,H9B,H9C)
;
_shelx_res_checksum              80547
_olex2_submission_special_instructions 'No special instructions were received'