Molecular engineering of nitrogen-rich helicene based organic semiconductors for stable perovskite solar cells.
Wei, Yuefang; Cai, Yaohang; He, Lifei; Zhang, Yuyan; Yuan, Yi; Zhang, Jing; Wang, Peng; Chemical science 14 (2023) 10285–10296; doi:10.1039/d3sc02845c

data_1569838
_publ_section_title
;
 Molecular engineering of nitrogen-rich helicene based organic
 semiconductors for stable perovskite solar cells.
;
_journal_issue                   37
_journal_name_full               'Chemical science'
_journal_page_first              10285
_journal_page_last               10296
_journal_paper_doi               10.1039/d3sc02845c
_journal_volume                  14
_journal_year                    2023
_chemical_formula_moiety         '2(C4 H8 O), C42 H27 N3'
_chemical_formula_sum            'C50 H43 N3 O2'
_chemical_formula_weight         717.87
_chemical_name_common            DAP
_chemical_name_systematic
20,21-dimethyl-20,21-dihydro-9H-dibenzo[a,i]benzo[4,5]indolo[3,2-c]benzo[4,5]indolo[2,3-g]carbazole
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-03-17
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2022-08-09 deposited with the CCDC.	2023-09-07 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.9480(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.8046(4)
_cell_length_b                   22.2850(7)
_cell_length_c                   15.2955(4)
_cell_measurement_reflns_used    9976
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      27.04
_cell_measurement_theta_min      2.43
_cell_volume                     3678.0(2)
_computing_cell_refinement       'SAINT V8.40B (Bruker Nano, Inc., 2019)'
_computing_data_collection       'Bruker Instrument Service vV6.2.14'
_computing_data_reduction        'SAINT V8.40B (Bruker Nano, Inc., 2019)'
_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      170.0
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'zju Bruker D8 Venture Ims3.0'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0757
_diffrn_reflns_av_unetI/netI     0.0348
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            72290
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.119
_diffrn_reflns_theta_min         2.097
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.7079
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1178 before and 0.0687 after correction.
The Ratio of minimum to maximum transmission is 0.9496.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            white
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.296
_exptl_crystal_description       block
_exptl_crystal_F_000             1520
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: THF'
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.628
_refine_diff_density_min         -0.633
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     511
_refine_ls_number_reflns         8116
_refine_ls_number_restraints     46
_refine_ls_restrained_S_all      5.703
_refine_ls_R_factor_all          0.0812
_refine_ls_R_factor_gt           0.0591
_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^)+(0.0744P)^2^+2.9964P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1482
_refine_ls_wR_factor_ref         0.1678
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6115
_reflns_number_total             8116
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3sc02845c2.cif
_cod_data_source_block           mo_210316_dap_0m
_cod_depositor_comments          'Adding full bibliography for 1569838.cif.'
_cod_database_code               1569838
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.993
_shelx_estimated_absorpt_t_min   0.991
_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, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C49-C50 \\sim C49-C50A
 with sigma of 0.02
 C50-O2 \\sim C50A-O2A
 with sigma of 0.02
 C47-O2 \\sim C47-O2A
 with sigma of 0.02
 C19-O2 \\sim C49-O2A
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
C49 \\sim O2 \\sim C50 \\sim O2A \\sim C50A: within 2A with sigma of 0.02 and
sigma for terminal atoms of 0.04
4. Others
 Sof(H47C)=Sof(H47D)=Sof(H49C)=Sof(H49D)=Sof(O2A)=Sof(C50A)=Sof(H50C)=
 Sof(H50D)=1-FVAR(1)
 Sof(H47A)=Sof(H47B)=Sof(H49A)=Sof(H49B)=Sof(O2)=Sof(C50)=Sof(H50A)=Sof(H50B)=
 FVAR(1)
 Fixed X: O2A(0.10253) C50A(0.157261)
 Fixed Y: O2A(0.926519) C50A(0.86261)
 Fixed Z: O2A(0.404929) C50A(0.39559)
5.a Secondary CH2 refined with riding coordinates:
 C43(H43A,H43B), C44(H44A,H44B), C45(H45A,H45B), C46(H46A,H46B), C47(H47A,
 H47B), C47(H47C,H47D), C48(H48A,H48B), C49(H49A,H49B), C49(H49C,H49D),
 C50(H50A,H50B), C50A(H50C,H50D)
5.b Aromatic/amide H refined with riding coordinates:
 N2(H2), C1(H1), C2(H2A), C3(H3), C4(H4), C7(H7), C8(H8), C17(H17), C18(H18),
 C19(H19), C20(H20), C27(H27), C28(H28), C29(H29), C30(H30), C33(H33), C34(H34),
  C37(H37), C38(H38), C39(H39), C40(H40)
5.c Idealised Me refined as rotating group:
 C41(H41A,H41B,H41C), C42(H42A,H42B,H42C)
;
_shelx_res_checksum              32473
_shelx_hkl_checksum              6136
_olex2_submission_special_instructions 'No special instructions were received'