Naphtho[1,2-b:4,3-b′]dithiophene-based hole transporting materials for high-performance perovskite solar cells: molecular engineering and opto-electronic properties
Cui, Bin-Bin; Yang, Ning; Shi, Congbo; Yang, Shuangshuang; Shao, Jiang-Yang; Han, Ying; Zhang, Liuzhu; Zhang, Qingshan; Zhong, Yu-Wu; Chen, Qi; Journal of Materials Chemistry A 6 (2018) 10057–; doi:10.1039/C8TA02071J

data_7237133
_publ_section_title
;
 Naphtho[1,2-b:4,3-b&#x2032;]dithiophene-based hole transporting materials
 for high-performance perovskite solar cells: molecular engineering and
 opto-electronic properties
;
_journal_issue                   21
_journal_name_full               'Journal of Materials Chemistry A'
_journal_page_first              10057
_journal_paper_doi               10.1039/C8TA02071J
_journal_volume                  6
_journal_year                    2018
_chemical_formula_moiety         '2(C H2 Cl2), C56 H46 N2 O6 S2'
_chemical_formula_sum            'C58 H50 Cl4 N2 O6 S2'
_chemical_formula_weight         1076.92
_chemical_name_systematic        NDT
_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   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2017-11-27
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2018-01-05 deposited with the CCDC.
2018-04-23 downloaded from the CCDC.
;
_cell_angle_alpha                90.32(3)
_cell_angle_beta                 95.79(3)
_cell_angle_gamma                109.07(3)
_cell_formula_units_Z            2
_cell_length_a                   11.237(2)
_cell_length_b                   12.606(3)
_cell_length_c                   19.298(4)
_cell_measurement_reflns_used    8362
_cell_measurement_temperature    153(2)
_cell_measurement_theta_max      27.4855
_cell_measurement_theta_min      2.0500
_cell_volume                     2568.3(11)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      153.15
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0368
_diffrn_reflns_av_unetI/netI     0.0446
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            30964
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.522
_diffrn_reflns_theta_min         1.061
_exptl_absorpt_coefficient_mu    0.367
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.7690
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2008)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.392
_exptl_crystal_description       block
_exptl_crystal_F_000             1120
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.619
_refine_diff_density_min         -0.917
_refine_diff_density_rms         0.128
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.153
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     665
_refine_ls_number_reflns         11743
_refine_ls_number_restraints     18
_refine_ls_restrained_S_all      1.157
_refine_ls_R_factor_all          0.0760
_refine_ls_R_factor_gt           0.0656
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1248P)^2^+1.7036P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1982
_refine_ls_wR_factor_ref         0.2237
_reflns_Friedel_coverage         0.000
_reflns_number_gt                10662
_reflns_number_total             11743
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8ta02071j2.cif
_cod_data_source_block           bwn17266
_cod_original_cell_volume        2568.5(10)
_cod_database_code               7237133
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.957
_shelx_estimated_absorpt_t_min   0.917
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
Cl3 \\sim Cl3A: within 1.7A with sigma of 0.01 and sigma for terminal atoms of
0.01
Uanis(Cl3) \\sim Ueq, Uanis(Cl3A) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.01
3. Others
 Sof(Cl3A)=1-FVAR(1)
 Sof(Cl3)=FVAR(1)
4.a Riding coordinates:
 C58(H58A,H58B)
4.b Secondary CH2 refined with riding coordinates:
 C57(H57A,H57B)
4.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C6(H6), C7(H7), C9(H9), C10(H10), C12(H12), C13(H13),
 C16(H16), C17(H17), C19(H19), C20(H20), C22(H22), C26(H26), C29(H29), C33(H33),
  C38(H38), C39(H39), C41(H41), C42(H42), C44(H44), C45(H45), C47(H47),
 C48(H48), C51(H51), C52(H52), C54(H54), C55(H55)
4.d Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C14(H14A,H14B,H14C), C35(H35A,H35B,H35C), C36(H36A,H36B,
 H36C), C49(H49A,H49B,H49C), C56(H56A,H56B,H56C)
;
_olex2_submission_special_instructions 'No special instructions were received'