Effect of alkyl chain length on the properties of triphenylamine-based hole transport materials and their performance in perovskite solar cells.
Fuentes Pineda, Rosinda; Troughton, Joel; Planells, Miquel; Sanchez-Molina Santos, Irene; Muhith, Farmin; Nichol, Gary S.; Haque, Saif; Watson, Trystan; Robertson, Neil; Physical chemistry chemical physics : PCCP 20 (2018) 1252–1260; doi:10.1039/c7cp07682g

data_7229708
_publ_section_title
;
 Effect of alkyl chain length on the properties of triphenylamine-based
 hole transport materials and their performance in perovskite solar cells.
;
_journal_issue                   2
_journal_name_full               'Physical chemistry chemical physics : PCCP'
_journal_page_first              1252
_journal_page_last               1260
_journal_paper_doi               10.1039/c7cp07682g
_journal_volume                  20
_journal_year                    2018
_chemical_formula_moiety         'C52 H52 N2 O4'
_chemical_formula_sum            'C52 H52 N2 O4'
_chemical_formula_weight         768.95
_chemical_name_systematic        iPrO-DATPA
_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     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2015-06-26
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_audit_update_record
;
2017-09-14 deposited with the CCDC.
2017-12-11 downloaded from the CCDC.
;
_cell_angle_alpha                100.569(2)
_cell_angle_beta                 90.6323(17)
_cell_angle_gamma                94.7035(18)
_cell_formula_units_Z            4
_cell_length_a                   12.4603(2)
_cell_length_b                   14.8711(4)
_cell_length_c                   24.3863(6)
_cell_measurement_reflns_used    19807
_cell_measurement_temperature    120.0
_cell_measurement_theta_max      30.7110
_cell_measurement_theta_min      3.3550
_cell_volume                     4425.55(18)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35e (release 07-10-2014 CrysAlis171 .NET)
(compiled Oct  7 2014,17:20:27)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35e (release 07-10-2014 CrysAlis171 .NET)
(compiled Oct  7 2014,17:20:27)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35e (release 07-10-2014 CrysAlis171 .NET)
(compiled Oct  7 2014,17:20:27)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      120.0
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1574
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
  1 omega  -44.00   61.00   0.5000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      -13.0850   77.0000  -30.0000 210

  2 omega  -87.00   18.00   0.5000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      -13.0850  -77.0000 -120.0000 210

  3 omega  -20.00   27.00   0.5000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      -13.0850  -99.0000  120.0000 94

  4 omega  -83.00   14.00   0.5000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      -13.0850  -57.0000    0.0000 194

  5 omega  -87.00   10.00   0.5000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      -13.0850  -77.0000  120.0000 194

  6 omega  -44.00   61.00   0.5000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      -13.0850   77.0000   90.0000 210

  7 omega  -40.00  -13.00   0.5000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      -13.0850  -77.0000  150.0000 54

  8 omega  -64.00  -37.00   0.5000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      -13.0850  -19.0000   30.0000 54

  9 omega  -87.00  -60.00   0.5000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      -13.0850  -19.0000   90.0000 54

 10 omega   -4.00   76.00   0.5000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       14.6475   38.0000  -90.0000 160
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Rigaku Oxford Diffraction SuperNova'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0036263000
_diffrn_orient_matrix_UB_12      0.0418790000
_diffrn_orient_matrix_UB_13      -0.0096311000
_diffrn_orient_matrix_UB_21      0.0566522000
_diffrn_orient_matrix_UB_22      0.0095074000
_diffrn_orient_matrix_UB_23      0.0033585000
_diffrn_orient_matrix_UB_31      0.0064848000
_diffrn_orient_matrix_UB_32      -0.0229619000
_diffrn_orient_matrix_UB_33      -0.0277854000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0382
_diffrn_reflns_av_unetI/netI     0.0338
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            88294
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         28.282
_diffrn_reflns_theta_min         2.992
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_diffrn_source_current           0.8
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    0.072
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.68870
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35e (release 07-10-2014 CrysAlis171 .NET)
(compiled Oct  7 2014,17:20:27)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.154
_exptl_crystal_description       block
_exptl_crystal_F_000             1640
_exptl_crystal_recrystallization_method
'The material was recrystallised from benzene by slow evaporation'
_exptl_crystal_size_max          0.5056
_exptl_crystal_size_mid          0.2263
_exptl_crystal_size_min          0.1028
_refine_diff_density_max         0.565
_refine_diff_density_min         -0.259
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1061
_refine_ls_number_reflns         21939
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0996
_refine_ls_R_factor_gt           0.0783
_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^)+(0.0845P)^2^+2.6882P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1920
_refine_ls_wR_factor_ref         0.2062
_reflns_Friedel_coverage         0.000
_reflns_number_gt                16792
_reflns_number_total             21939
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7cp07682g2.cif
_cod_data_source_block           nr15005
_cod_depositor_comments
'Adding full bibliography for 7229705--7229708.cif.'
_cod_original_cell_volume        4425.56(18)
_cod_database_code               7229708
_chemical_oxdiff_formula         'C52 H52 N2 O4'
_chemical_oxdiff_usercomment     '@ 120 K iPrO-DATPA'
_reflns_odcompleteness_completeness 99.85
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     28.22
_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.a Ternary CH refined with riding coordinates:
 C16(H16), C17(H17), C41(H41), C42(H42), C116(H116), C117(H117), C166(H166),
 C167(H167)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C9(H9), C10(H10), C12(H12), C13(H13),
 C19(H19), C20(H20), C22(H22), C23(H23), C27(H27), C28(H28), C30(H30), C31(H31),
  C34(H34), C35(H35), C37(H37), C38(H38), C44(H44), C45(H45), C47(H47),
 C48(H48), C102(H102), C103(H103), C105(H105), C106(H106), C109(H109),
 C110(H110), C112(H112), C113(H113), C119(H119), C120(H120), C122(H122),
 C123(H123), C152(H152), C153(H153), C155(H155), C156(H156), C159(H159),
 C160(H160), C162(H162), C163(H163), C169(H169), C170(H170), C172(H172),
 C173(H173)
2.c Idealised Me refined as rotating group:
 C51(H51A,H51B,H51C), C52(H52A,H52B,H52C), C53(H53A,H53B,H53C), C54(H54A,H54B,
 H54C), C55(H55A,H55B,H55C), C56(H56A,H56B,H56C), C57(H57A,H57B,H57C), C58(H58A,
 H58B,H58C), C126(H12A,H12B,H12C), C127(H12D,H12E,H12F), C128(H12G,H12H,H12I),
 C129(H12J,H12K,H12L), C176(H17A,H17B,H17C), C177(H17D,H17E,H17F), C178(H17G,
 H17H,H17I), C179(H17J,H17K,H17L)
;
_shelx_res_checksum              72469
_shelx_hkl_checksum              19397
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_data_collection 2015-06-25
_olex2_date_sample_submission    2015-06-01
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems Cryostream 700+'
_olex2_exptl_crystal_mounting_method
'The crystal was mounted on a MITIGEN holder in oil'
_olex2_submission_original_sample_id iPrO-DATPA
_olex2_submission_special_instructions 'No special instructions were received'