A triple helicene based molecular semiconductor characteristic of a fully fused conjugated backbone for perovskite solar cells
Fang, Lingyi; Zhang, Yuyan; Ren, Ming; Xie, Xinrui; Li, Tianyu; Yuan, Yi; Zhang, Jing; Wang, Peng; Energy & Environmental Science 15 (2022) 1630–1637; doi:10.1039/D1EE02843J

data_1566632
_publ_section_title
;
 A triple helicene based molecular semiconductor characteristic of a fully
 fused conjugated backbone for perovskite solar cells
;
_journal_issue                   4
_journal_name_full               'Energy &amp; Environmental Science'
_journal_page_first              1630
_journal_page_last               1637
_journal_paper_doi               10.1039/D1EE02843J
_journal_volume                  15
_journal_year                    2022
_chemical_formula_moiety         'C78 H78 N6 O3'
_chemical_formula_sum            'C78 H78 N6 O3'
_chemical_formula_weight         1147.46
_chemical_name_systematic        TBPC-611
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2020-09-20
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-01-13 deposited with the CCDC.	2022-02-28 downloaded from the CCDC.
;
_cell_angle_alpha                79.038(2)
_cell_angle_beta                 72.546(2)
_cell_angle_gamma                68.828(2)
_cell_formula_units_Z            2
_cell_length_a                   14.2538(6)
_cell_length_b                   17.1903(7)
_cell_length_c                   17.3592(7)
_cell_measurement_reflns_used    9217
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      48.455
_cell_measurement_theta_min      2.408
_cell_volume                     3767.7(3)
_computing_cell_refinement       'SAINT V8.40A (?, 2016)'
_computing_data_reduction        'SAINT V8.40A (?, 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      150.0
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_device_type  'BRUKER D8 VENTURE PHOTON III'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34138
_diffrn_reflns_av_R_equivalents  0.0512
_diffrn_reflns_av_unetI/netI     0.0610
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            60426
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         57.368
_diffrn_reflns_theta_min         2.331
_diffrn_source                   'Iiquid target Source'
_exptl_absorpt_coefficient_mu    0.308
_exptl_absorpt_correction_T_max  0.7512
_exptl_absorpt_correction_T_min  0.6318
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1062 before and 0.0600 after correction.
The Ratio of minimum to maximum transmission is 0.8411.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.011
_exptl_crystal_description       block
_exptl_crystal_F_000             1224
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.667
_refine_diff_density_min         -0.533
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.130
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     868
_refine_ls_number_reflns         15322
_refine_ls_number_restraints     199
_refine_ls_restrained_S_all      1.224
_refine_ls_R_factor_all          0.1545
_refine_ls_R_factor_gt           0.0949
_refine_ls_shift/su_max          0.090
_refine_ls_shift/su_mean         0.005
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2951
_refine_ls_wR_factor_ref         0.3382
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7777
_reflns_number_total             15322
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ee02843j2.cif
_cod_data_source_block           b20090302b0087_0m_sq
_cod_depositor_comments          'Adding full bibliography for 1566632.cif.'
_cod_database_code               1566632
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.982
_shelx_estimated_absorpt_t_min   0.941
_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, All C(H,H,H,H,H,H) groups
2. Restrained distances
 C71-C72
 1.53 with sigma of 0.02
 C72-C73
 1.53 with sigma of 0.02
 C73-C74
 1.53 with sigma of 0.02
 C74-C75
 1.53 with sigma of 0.02
 C71-C72A
 1.53 with sigma of 0.02
 C72A-C73A
 1.53 with sigma of 0.02
 C73A-C74A
 1.53 with sigma of 0.02
 C74A-C75A
 1.53 with sigma of 0.02
 C63-C64
 1.53 with sigma of 0.02
 C63-C64A
 1.53 with sigma of 0.02
 C64A-C65A
 1.53 with sigma of 0.02
 C65A-C66A
 1.53 with sigma of 0.02
 C66A-C67A
 1.53 with sigma of 0.02
 C75-C76
 1.53 with sigma of 0.02
 C67A-C68A
 1.53 with sigma of 0.02
 C63-N4 = C63-H63A = C63-H63B = C63-C64
 1.53 with sigma of 0.02
 C64-C65
 1.53 with sigma of 0.02
 C65-C66
 1.53 with sigma of 0.01
 C71-C73
 2.5 with sigma of 0.04
 C72-C74
 2.5 with sigma of 0.04
 C73-C75
 2.5 with sigma of 0.04
 C71-C73A
 2.5 with sigma of 0.04
 C72A-C74A
 2.5 with sigma of 0.04
 C73A-C75A
 2.5 with sigma of 0.04
 C63-C65A
 2.5 with sigma of 0.04
 C64A-C66A
 2.5 with sigma of 0.04
 C65A-C67A
 2.5 with sigma of 0.04
 C74-C76
 2.5 with sigma of 0.04
 C74A-C76
 2.5 with sigma of 0.04
 C66A-C68A
 2.5 with sigma of 0.04
3. Rigid bond restraints
 C36, C37, C38
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 C43, C44
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
4. Uiso/Uaniso restraints and constraints
C63 \\sim C64A \\sim C65A \\sim C66A \\sim C67A: within 1.7A with sigma of
0.001 and sigma for terminal atoms of 0.002
C71 \\sim C76 \\sim C72 \\sim C73 \\sim C74 \\sim C75 \\sim C72A \\sim C73A
\\sim C74A \\sim C75A: within 1.7A with sigma of 0.02 and sigma for terminal
atoms of 0.04
C63 \\sim C64 \\sim C65 \\sim C66 \\sim C67 \\sim C68: within 1.7A with sigma
of 0.02 and sigma for terminal atoms of 0.04
C63 \\sim C64A \\sim C65A \\sim C66A \\sim C67A \\sim C68A: within 1.7A with
sigma of 0.02 and sigma for terminal atoms of 0.04
Uanis(C68) = Uanis(C68A)
5. Others
 Sof(H71C)=Sof(H71D)=Sof(H76D)=Sof(H76E)=Sof(H76F)=Sof(C72A)=Sof(H72C)=
 Sof(H72D)=Sof(C73A)=Sof(H73C)=Sof(H73D)=Sof(C74A)=Sof(H74C)=Sof(H74D)=
 Sof(C75A)=Sof(H75C)=Sof(H75D)=1-FVAR(1)
 Sof(H71A)=Sof(H71B)=Sof(H76A)=Sof(H76B)=Sof(H76C)=Sof(C72)=Sof(H72A)=
 Sof(H72B)=Sof(C73)=Sof(H73A)=Sof(H73B)=Sof(C74)=Sof(H74A)=Sof(H74B)=Sof(C75)=
 Sof(H75A)=Sof(H75B)=FVAR(1)
 Sof(H63C)=Sof(H63D)=Sof(C64A)=Sof(H64C)=Sof(H64D)=Sof(C65A)=Sof(H65C)=
 Sof(H65D)=Sof(C66A)=Sof(H66C)=Sof(H66D)=Sof(C67A)=Sof(H67C)=Sof(H67D)=
 Sof(C68A)=Sof(H68D)=Sof(H68E)=Sof(H68F)=1-FVAR(2)
 Sof(H63A)=Sof(H63B)=Sof(C64)=Sof(H64A)=Sof(H64B)=Sof(C65)=Sof(H65A)=Sof(H65B)=
 Sof(C66)=Sof(H66A)=Sof(H66B)=Sof(C67)=Sof(H67A)=Sof(H67B)=Sof(C68)=Sof(H68A)=
 Sof(H68B)=Sof(H68C)=FVAR(2)
6.a Secondary CH2 refined with riding coordinates:
 C57(H57A,H57B), C58(H58A,H58B), C59(H59A,H59B), C60(H60A,H60B), C61(H61A,
 H61B), C63(H63A,H63B), C63(H63C,H63D), C71(H71A,H71B), C71(H71C,H71D),
 C64(H64A,H64B), C65(H65A,H65B), C66(H66A,H66B), C67(H67A,H67B), C72(H72A,H72B),
  C73(H73A,H73B), C74(H74A,H74B), C75(H75A,H75B), C64A(H64C,H64D), C65A(H65C,
 H65D), C66A(H66C,H66D), C67A(H67C,H67D), C72A(H72C,H72D), C73A(H73C,H73D),
 C74A(H74C,H74D), C75A(H75C,H75D)
6.b Me refined with riding coordinates:
 C76(H76A,H76B,H76C), C76(H76D,H76E,H76F), C68(H68A,H68B,H68C), C68A(H68D,H68E,
 H68F)
6.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C3(H3), C4(H4), C11(H11), C12(H12), C13(H13), C14(H14), C29(H29),
 C30(H30), C31(H31), C32(H32), C35(H35), C37(H37), C38(H38), C43(H43), C44(H44),
  C45(H45), C46(H46), C51(H51), C52(H52), C54(H54)
6.d Idealised Me refined as rotating group:
 C55(H55A,H55B,H55C), C56(H56A,H56B,H56C), C62(H62A,H62B,H62C), C69(H69A,H69B,
 H69C), C70(H70A,H70B,H70C), C77(H77A,H77B,H77C), C78(H78A,H78B,H78C)
;
_shelx_res_checksum              12485
_shelx_fab_checksum              58184
_olex2_submission_special_instructions 'No special instructions were received'