Low cost and stable quinoxaline-based hole-transporting materials with a D-A-D molecular configuration for efficient perovskite solar cells.
Zhang, Hao; Wu, Yongzhen; Zhang, Weiwei; Li, Erpeng; Shen, Chao; Jiang, Huiyun; Tian, He; Zhu, Wei-Hong; Chemical science 9 (2018) 5919–5928; doi:10.1039/c8sc00731d

data_1549543
_publ_section_title
;
 Low cost and stable quinoxaline-based hole-transporting materials with a
 D-A-D molecular configuration for efficient perovskite solar cells.
;
_journal_issue                   27
_journal_name_full               'Chemical science'
_journal_page_first              5919
_journal_page_last               5928
_journal_paper_doi               10.1039/c8sc00731d
_journal_volume                  9
_journal_year                    2018
_chemical_formula_moiety         'C60 H48 N4 O4'
_chemical_formula_sum            'C60 H48 N4 O4'
_chemical_formula_weight         889.02
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2017-06-27
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_audit_update_record
;
2018-02-13 deposited with the CCDC.
2018-06-13 downloaded from the CCDC.
;
_cell_angle_alpha                88.379(4)
_cell_angle_beta                 81.381(4)
_cell_angle_gamma                74.642(4)
_cell_formula_units_Z            2
_cell_length_a                   12.0014(12)
_cell_length_b                   13.0411(12)
_cell_length_c                   17.0476(15)
_cell_measurement_reflns_used    4207
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      26.281
_cell_measurement_theta_min      2.417
_cell_volume                     2543.6(4)
_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      173.01
_diffrn_measured_fraction_theta_full 0.974
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measurement_device_type  'Bruker D8Venture'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1287
_diffrn_reflns_av_unetI/netI     0.1232
_diffrn_reflns_Laue_measured_fraction_full 0.974
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            33930
_diffrn_reflns_point_group_measured_fraction_full 0.974
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.500
_diffrn_reflns_theta_min         2.514
_exptl_absorpt_coefficient_mu    0.073
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5361
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1504 before and 0.0877 after correction. The Ratio of minimum to maximum transmission is 0.7190. The \l/2 correction factor is Not present.'
_exptl_crystal_density_diffrn    1.161
_exptl_crystal_description       block
_exptl_crystal_F_000             936
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.267
_refine_diff_density_min         -0.303
_refine_diff_density_rms         0.054
_refine_ls_extinction_coef       0.024(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/8 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     647
_refine_ls_number_reflns         9238
_refine_ls_number_restraints     44
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.1954
_refine_ls_R_factor_gt           0.0990
_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^)+(0.1219P)^2^+1.2160P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2315
_refine_ls_wR_factor_ref         0.2991
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4063
_reflns_number_total             9238
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8sc00731d2.cif
_cod_data_source_block           mo_d8v17152_0m
_cod_depositor_comments
'Adding full bibliography for 1549543--1549544.cif.'
_cod_database_code               1549543
_shelx_shelxl_version_number     2014/8
_shelx_estimated_absorpt_t_max   0.999
_shelx_estimated_absorpt_t_min   0.989
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 O4-C57
 1.48 with sigma of 0.02
 O4'-C60' = O4-C60
 1.48 with sigma of 0.02
 O2-C46 = O2-C43
 1.48 with sigma of 0.02
 O2-C46' = O2-C46 = O2-C43
 1.48 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
C21 \\sim C24 \\sim C25 \\sim C26: within 2A with sigma of 0.01 and sigma for
terminal atoms of 0.02
O2 \\sim C43 \\sim C46 \\sim C46': within 2A with sigma of 0.01 and sigma for
terminal atoms of 0.02
4. Others
 Fixed Sof: C46(0.75) H46A(0.75) H46B(0.75) H46C(0.75) C46'(0.25) H46D(0.25)
 H46E(0.25) H46F(0.25) O4(0.5) C60(0.5) H60D(0.5) H60E(0.5) H60F(0.5) O4'(0.5)
 C60'(0.5) H60A(0.5) H60B(0.5) H60C(0.5)
5.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C10(H10), C11(H11), C12(H12), C13(H13), C14(H14), C16(H16),
 C17(H17), C18(H18), C19(H19), C20(H20), C22(H22), C23(H23), C25(H25), C26(H26),
  C28(H28), C29(H29), C31(H31), C32(H32), C34(H34), C35(H35), C37(H37),
 C38(H38), C41(H41), C42(H42), C44(H44), C45(H45), C48(H48), C49(H49), C51(H51),
  C52(H52), C55(H55), C56(H56), C58(H58), C59(H59)
5.b Idealised Me refined as rotating group:
 C39(H39A,H39B,H39C), C46(H46A,H46B,H46C), C46'(H46D,H46E,H46F), C53(H53A,H53B,
 H53C), C60(H60D,H60E,H60F), C60'(H60A,H60B,H60C)
;
_shelx_res_checksum              12613
_shelx_fab_checksum              41408
_olex2_submission_special_instructions 'No special instructions were received'