A Pyrrole-Bridged Bis(oxa[5]helicene)-Based Molecular Semiconductor for Efficient and Durable Perovskite Solar Cells: Microscopic Insights
Wei, Yuefang; Zheng, Aibin; Xie, Xinrui; Zhang, Jingfeng; He, Lifei; Wang, Peng; ACS Materials Letters  (2021) 947–955; doi:10.1021/acsmaterialslett.1c00291

data_4518758
_publ_section_title
;
 A Pyrrole-Bridged Bis(oxa[5]helicene)-Based Molecular Semiconductor for
 Efficient and Durable Perovskite Solar Cells: Microscopic Insights
;
_journal_name_full               'ACS Materials Letters'
_journal_page_first              947
_journal_page_last               955
_journal_paper_doi               10.1021/acsmaterialslett.1c00291
_journal_year                    2021
_chemical_formula_moiety         'C68 H47 N3 O6, 3(C4 H8 O)'
_chemical_formula_sum            'C80 H71 N3 O9'
_chemical_formula_weight         1218.39
_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             2019-10-25
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90.558(2)
_cell_angle_beta                 93.660(2)
_cell_angle_gamma                93.443(2)
_cell_formula_units_Z            2
_cell_length_a                   11.0437(5)
_cell_length_b                   16.1591(7)
_cell_length_c                   17.4300(7)
_cell_measurement_reflns_used    9927
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      26.95
_cell_measurement_theta_min      2.30
_cell_volume                     3098.3(2)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 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      170.0
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0506
_diffrn_reflns_av_unetI/netI     0.0412
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            59907
_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         27.115
_diffrn_reflns_theta_min         2.254
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.6495
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0947 before and 0.0557 after correction.
The Ratio of minimum to maximum transmission is 0.8712.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.306
_exptl_crystal_description       plate
_exptl_crystal_F_000             1288
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.493
_refine_diff_density_min         -0.416
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     879
_refine_ls_number_reflns         13657
_refine_ls_number_restraints     123
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0777
_refine_ls_R_factor_gt           0.0522
_refine_ls_shift/su_max          0.007
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0646P)^2^+1.2393P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1302
_refine_ls_wR_factor_ref         0.1464
_reflns_Friedel_coverage         0.000
_reflns_number_gt                9693
_reflns_number_total             13657
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            tz1c00291_si_002.cif
_cod_data_source_block           191024_x3_0m
_cod_database_code               4518758
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.996
_shelx_estimated_absorpt_t_min   0.984
_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. Restrained distances
 C80A-C78A
 2.43 with sigma of 0.02
 C79A-C77A
 2.43 with sigma of 0.02
 C78A-O9A
 2.43 with sigma of 0.02
 C77A-C80A
 2.43 with sigma of 0.02
 O9A-C79A
 2.43 with sigma of 0.02
 C80-C79 \\sim C80A-C79A
 with sigma of 0.02
 C80-O9 \\sim C80A-O9A
 with sigma of 0.02
 C78-C79 \\sim C78A-C79A
 with sigma of 0.02
 C78-C77 \\sim C78A-C77A
 with sigma of 0.02
 O9-C77 \\sim O9A-C77A
 with sigma of 0.02
 C80-C78 \\sim C80A-C78A
 with sigma of 0.04
 C80-C77 \\sim C80A-C77A
 with sigma of 0.04
 C78-O9 \\sim C78A-O9A
 with sigma of 0.04
 C79-O9 \\sim C79A-O9A
 with sigma of 0.04
 C79-C77 \\sim C79A-C77A
 with sigma of 0.04
3. Uiso/Uaniso restraints and constraints
C77 \\sim C78 \\sim C80 \\sim C79 \\sim O9 \\sim C79A \\sim C80A \\sim O9A
\\sim C77A: within 1.7A with sigma of 0.02 and sigma for terminal atoms of 0.04
4. Others
 Sof(O9A)=Sof(C77A)=Sof(H77C)=Sof(H77D)=Sof(C78A)=Sof(H78C)=Sof(H78D)=
 Sof(C79A)=Sof(H79C)=Sof(H79D)=Sof(C80A)=Sof(H80C)=Sof(H80D)=1-FVAR(1)
 Sof(C80)=Sof(H80A)=Sof(H80B)=Sof(C78)=Sof(H78A)=Sof(H78B)=Sof(C79)=Sof(H79A)=
 Sof(H79B)=Sof(O9)=Sof(C77)=Sof(H77A)=Sof(H77B)=FVAR(1)
5.a Secondary CH2 refined with riding coordinates:
 C72(H72A,H72B), C69(H69A,H69B), C71(H71A,H71B), C76(H76A,H76B), C73(H73A,
 H73B), C80(H80A,H80B), C70(H70A,H70B), C78(H78A,H78B), C75(H75A,H75B),
 C79(H79A,H79B), C74(H74A,H74B), C77(H77A,H77B), C77A(H77C,H77D), C78A(H78C,
 H78D), C79A(H79C,H79D), C80A(H80C,H80D)
5.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C33(H33), C30(H30), C27(H27), C8(H8), C4(H4), C37(H37), C20(H20),
 C29(H29), C28(H28), C53(H53), C17(H17), C1(H1A), C40(H40), C60(H60), C46(H46),
 C63(H63), C19(H19), C38(H38), C3(H3), C18(H18), C66(H66), C50(H50), C56(H56),
 C67(H67), C39(H39), C49(H49), C59(H59), C52(H52), C64(H64), C57(H57), C45(H45),
  C2(H2), C42(H42), C43(H43)
5.c Idealised Me refined as rotating group:
 C68(H68A,H68B,H68C), C54(H54A,H54B,H54C), C61(H61A,H61B,H61C), C47(H47A,H47B,
 H47C)
;
_shelx_res_checksum              97165
_shelx_hkl_checksum              40298
_olex2_submission_special_instructions 'No special instructions were received'