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_7229707
_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         'C56 H60 N2 O4'
_chemical_formula_sum            'C56 H60 N2 O4'
_chemical_formula_weight         825.06
_chemical_name_systematic        BuO-DATPA
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2015-08-13
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_audit_update_record
;
2017-09-15 deposited with the CCDC.
2017-12-11 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 93.5009(5)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   11.82431(7)
_cell_length_b                   13.11889(7)
_cell_length_c                   14.97854(9)
_cell_measurement_reflns_used    35031
_cell_measurement_temperature    120.0
_cell_measurement_theta_max      75.9980
_cell_measurement_theta_min      4.4480
_cell_volume                     2319.16(2)
_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)'
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_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_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 0.997
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details
;
  1 omega  -50.00   29.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
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  2 omega  -70.00   27.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
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  3 omega -113.00  -17.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
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  4 omega  -50.00   29.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
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  5 omega    1.00   83.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
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  6 omega   23.00   98.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
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  7 omega   40.00   99.00   1.0000   10.0000
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  8 omega   30.00  109.00   1.0000   10.0000
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  9 omega   37.00  142.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
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 10 omega   39.00  121.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
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 11 omega   39.00  121.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000 -125.0000   90.0000 82

 12 omega   83.00  178.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000   61.0000  -90.0000 95

 13 omega   94.00  178.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  125.0000 -150.0000 84

 14 omega   39.00  121.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000 -125.0000 -180.0000 82

 15 omega   30.00  109.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
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 16 omega   36.00   91.00   1.0000   10.0000
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 17 omega   36.00   91.00   1.0000   10.0000
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 18 omega   36.00   91.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
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 19 omega   41.00  139.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
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 20 omega   30.00  109.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  -94.0000 -120.0000 79

 21 omega   36.00   91.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  -30.0000  -60.0000 55

 22 omega   40.00   99.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  -45.0000   60.0000 59

 23 omega   39.00  121.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000 -125.0000  120.0000 82

 24 omega   36.00   91.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  -30.0000 -180.0000 55

 25 omega   87.00  178.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000   30.0000   90.0000 91

 26 omega   39.00  121.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000 -125.0000  -60.0000 82

 27 omega   94.00  178.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  125.0000  -60.0000 84

 28 omega   30.00  109.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  -94.0000  -60.0000 79

 29 omega   36.00   91.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  -30.0000  -30.0000 55

 30 omega   24.00  178.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000    0.0000 -120.0000 154

 31 omega  -50.00   29.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -43.1686   38.0000   30.0000 79

 32 omega -117.00  -12.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -43.1686  -77.0000 -120.0000 105

 33 omega -117.00  -12.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -43.1686  -77.0000  150.0000 105

 34 omega -117.00  -12.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -43.1686  -77.0000   60.0000 105

 35 omega -122.00   -6.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -43.1686  -19.0000  -30.0000 116

 36 omega -117.00  -12.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -43.1686  -77.0000  -30.0000 105

 37 omega   21.00  116.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       43.1686   38.0000  120.0000 95

 38 omega   83.00  178.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000   61.0000    0.0000 95

 39 omega   80.00  178.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000   77.0000   90.0000 98

 40 omega   82.00  178.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000   69.0000 -157.9918 96

 41 omega   83.00  178.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000   61.0000  150.0000 95

 42 omega   83.00  178.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000   61.0000  -60.0000 95

 43 omega   83.00  178.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000   61.0000   30.0000 95

 44 omega   83.00  149.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000   61.0000 -120.0000 66

 45 omega   87.00  178.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000   30.0000    0.0000 91
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Rigaku Oxford Diffraction SuperNova'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0824241000
_diffrn_orient_matrix_UB_12      0.0135858000
_diffrn_orient_matrix_UB_13      0.0828120000
_diffrn_orient_matrix_UB_21      0.0477138000
_diffrn_orient_matrix_UB_22      0.0971869000
_diffrn_orient_matrix_UB_23      -0.0415284000
_diffrn_orient_matrix_UB_31      -0.0892862000
_diffrn_orient_matrix_UB_32      0.0644959000
_diffrn_orient_matrix_UB_33      0.0450901000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0378
_diffrn_reflns_av_unetI/netI     0.0132
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.996
_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       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            56181
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.172
_diffrn_reflns_theta_min         3.745
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.572
_exptl_absorpt_correction_T_max  0.997
_exptl_absorpt_correction_T_min  0.995
_exptl_absorpt_correction_type   gaussian
_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)
Numerical absorption correction based on gaussian integration over
            a multifaceted crystal model
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    1.181
_exptl_crystal_description       block
_exptl_crystal_F_000             884
_exptl_crystal_recrystallization_method
'The material was recrystallised from benzene by slow evaporation'
_exptl_crystal_size_max          0.2453
_exptl_crystal_size_mid          0.2376
_exptl_crystal_size_min          0.1394
_refine_diff_density_max         0.472
_refine_diff_density_min         -0.389
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     320
_refine_ls_number_reflns         4833
_refine_ls_number_restraints     45
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.0598
_refine_ls_R_factor_gt           0.0578
_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^)+(0.0871P)^2^+0.9714P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1536
_refine_ls_wR_factor_ref         0.1559
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4563
_reflns_number_total             4833
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7cp07682g2.cif
_cod_data_source_block           nr15007
_cod_depositor_comments
'Adding full bibliography for 7229705--7229708.cif.'
_cod_database_code               7229707
_chemical_oxdiff_formula         'C56 H60 N2 O4'
_chemical_oxdiff_usercomment     '@ 120 K BuO_DATPA'
_reflns_odcompleteness_completeness 99.72
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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. Rigid body (RIGU) restrains
 C16, C26, C27, C30
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C16A, C26A, C27A, C30A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
3. Same fragment restrains
{C17, C28, C29, C31} sigma for 1-2: 0.02, 1-3: 0.02
as
{C16, C26, C27, C30}
{C17, C28, C29, C31} sigma for 1-2: 0.02, 1-3: 0.02
as
{C16A, C26A, C27A, C30A}
4. Others
 Sof(C16A)=Sof(H16C)=Sof(H16D)=Sof(C26A)=Sof(H26C)=Sof(H26D)=Sof(C27A)=
 Sof(H27C)=Sof(H27D)=Sof(C30A)=Sof(H30D)=Sof(H30E)=Sof(H30F)=1-FVAR(1)
 Sof(C16)=Sof(H16A)=Sof(H16B)=Sof(C26)=Sof(H26A)=Sof(H26B)=Sof(C27)=Sof(H27A)=
 Sof(H27B)=Sof(C30)=Sof(H30A)=Sof(H30B)=Sof(H30C)=FVAR(1)
5.a Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B), C26(H26A,H26B), C27(H27A,H27B), C16A(H16C,H16D), C26A(H26C,
 H26D), C27A(H27C,H27D), C17(H17A,H17B), C28(H28A,H28B), C29(H29A,H29B)
5.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)
5.c Idealised Me refined as rotating group:
 C30(H30A,H30B,H30C), C30A(H30D,H30E,H30F), C31(H31A,H31B,H31C)
;
_shelx_res_checksum              58339
_shelx_hkl_checksum              55530
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_data_collection 2015-06-12
_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 Paratone oil'
_olex2_submission_original_sample_id BuO_DATPA
_olex2_submission_special_instructions 'No special instructions were received'