Effects of Self-Assembly on the Photogeneration of Radical Cations in Halogenated Triphenylamines
Hossain, Muhammad Saddam; Sindt, Ammon J.; Goodlett, Dustin W.; Shields, Dylan J.; O’Connor, Colin J.; Antevska, Aleksandra; Karakalos, Stavros G.; Smith, Mark D.; Garashchuk, Sophya; Do, Thanh D.; Gudmundsdottir, Anna D.; Shimizu, Linda S.; The Journal of Physical Chemistry C 125 (2021) 19991–20002; doi:10.1021/acs.jpcc.1c04933

data_1564808
_publ_section_title
;
 Effects of Self-Assembly on the Photogeneration of Radical Cations in
 Halogenated Triphenylamines
;
_journal_issue                   36
_journal_name_full               'The Journal of Physical Chemistry C'
_journal_page_first              19991
_journal_page_last               20002
_journal_paper_doi               10.1021/acs.jpcc.1c04933
_journal_volume                  125
_journal_year                    2021
_chemical_formula_moiety         'C39 H32 Cl2 N4 O'
_chemical_formula_sum            'C39 H32 Cl2 N4 O'
_chemical_formula_weight         643.58
_space_group_crystal_system      orthorhombic
_space_group_IT_number           56
_space_group_name_Hall           '-P 2ab 2ac'
_space_group_name_H-M_alt        'P c c n'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2019-06-28
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   18.4725(12)
_cell_length_b                   19.8765(13)
_cell_length_c                   8.9785(6)
_cell_measurement_reflns_used    9151
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.384
_cell_measurement_theta_min      2.723
_cell_volume                     3296.6(4)
_computing_cell_refinement       'SAINT+ Ver. 8.38A (Bruker-AXS, 2016)'
_computing_data_collection       'Bruker APEX3 v2016.5-0 (Bruker, 2016)'
_computing_data_reduction        'SAINT+ Ver. 8.38A (Bruker-AXS, 2016)'
_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    'XT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Bruker PHOTON-100 area detector'
_diffrn_detector_area_resol_mean 10.4
_diffrn_detector_type            'CMOS area detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 QUEST'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0661
_diffrn_reflns_av_unetI/netI     0.0199
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            62942
_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         26.418
_diffrn_reflns_theta_min         1.505
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.235
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6905
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0974 before and 0.0611 after correction.
The Ratio of minimum to maximum transmission is 0.9263.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.297
_exptl_crystal_description       needle
_exptl_crystal_F_000             1344
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.269
_refine_diff_density_min         -0.378
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     286
_refine_ls_number_reflns         3378
_refine_ls_number_restraints     72
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.0562
_refine_ls_R_factor_gt           0.0418
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0536P)^2^+2.1250P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1028
_refine_ls_wR_factor_ref         0.1131
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2733
_reflns_number_total             3378
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jp1c04933_si_002.cif
_cod_data_source_block           tpa_cl_la
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_diffrn_radiation_probe' value 'X-ray' was changed to
'x-ray' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/current/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 
;
_cod_database_code               1564808
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.986
_shelx_estimated_absorpt_t_min   0.946
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Shared sites
{O1A, O1B}
{C1A, C1B}
3. Restrained distances
 N1B-H1A = N1A-H1A
 0.84 with sigma of 0.02
 C11B-Cl1B \\sim C13B-Cl1B
 with sigma of 0.005
4. Restrained planarity
 N2B, C9B, C10B, C11B, C12B, Cl1B, C13B, C14B
 with sigma of 0.01
 N2B, C15B, C16B, C17B, C18B, C19B, C20B
 with sigma of 0.01
5. Uiso/Uaniso restraints and constraints
Uanis(O1A) = Uanis(O1B)
Uanis(C1A) = Uanis(C1B)
Uanis(N1B) = Uanis(N1A)
Uanis(C2B) = Uanis(C2A)
Uanis(C3B) = Uanis(C3A)
Uanis(C6B) = Uanis(C7A)
Uanis(C7B) = Uanis(C6A)
Uanis(C4A) = Uanis(C8B)
Uanis(C8A) = Uanis(C5B)
Uanis(C20A) = Uanis(C16B)
Uanis(C17B) = Uanis(C19A)
Uanis(C18B) = Uanis(C18A)
Uanis(C19B) = Uanis(C17A)
Uanis(C16A) = Uanis(C20B)
Uanis(C8A) = Uanis(C4B)
Uanis(C13B) = Uanis(C14A)
Uanis(C13A) = Uanis(C12B)
Uanis(C11B) = Uanis(C12A)
Uanis(C10B) = Uanis(C11A)
Uanis(C9B) = Uanis(C10A)
Uanis(C9A) = Uanis(C14B)
Uanis(N2A) = Uanis(N2B)
Uanis(C15B) = Uanis(C15A)
6. Same fragment restrains
{Cl1A, O1A, N1A, N2A, C1A, C2A, C3A, C4A, C5A, C6A, C7A, C8A, C9A, C10A, C11A,
C12A, C13A, C14A, C15A, C16A, C17A, C18A, C19A, C20A} sigma for 1-2: 0.015,
1-3: 0.04
as
{Cl1B, O1B, N1B, N2B, C1B, C2B, C3B, C4B, C5B, C6B, C7B, C8B, C9B, C10B, C11B,
C12B, C13B, C14B, C15B, C16B, C17B, C18B, C19B, C20B}
7. Others
 Sof(Cl1B)=Sof(N1B)=Sof(N2B)=Sof(C2B)=Sof(H2BA)=Sof(H2BB)=Sof(C3B)=Sof(C4B)=
 Sof(H4B)=Sof(C5B)=Sof(H5B)=Sof(C6B)=Sof(C7B)=Sof(H7B)=Sof(C8B)=Sof(H8B)=
 Sof(C9B)=Sof(C10B)=Sof(H10B)=Sof(C11B)=Sof(H11B)=Sof(C12B)=Sof(C13B)=Sof(H13B)=
 Sof(C14B)=Sof(H14B)=Sof(C15B)=Sof(C16B)=Sof(H16B)=Sof(C17B)=Sof(H17B)=
 Sof(C18B)=Sof(H18B)=Sof(C19B)=Sof(H19B)=Sof(C20B)=Sof(H20B)=1-FVAR(1)
 Sof(O1B)=Sof(C1B)=0.5*(1-FVAR(2))
 Sof(O1A)=Sof(C1A)=0.5*FVAR(2)
 Sof(Cl1A)=Sof(N1A)=Sof(N2A)=Sof(C2A)=Sof(H2AA)=Sof(H2AB)=Sof(C3A)=Sof(C4A)=
 Sof(H4A)=Sof(C5A)=Sof(H5A)=Sof(C6A)=Sof(C7A)=Sof(H7A)=Sof(C8A)=Sof(H8A)=
 Sof(C9A)=Sof(C10A)=Sof(H10A)=Sof(C11A)=Sof(H11A)=Sof(C12A)=Sof(C13A)=Sof(H13A)=
 Sof(C14A)=Sof(H14A)=Sof(C15A)=Sof(C16A)=Sof(H16A)=Sof(C17A)=Sof(H17A)=
 Sof(C18A)=Sof(H18A)=Sof(C19A)=Sof(H19A)=Sof(C20A)=Sof(H20A)=FVAR(1)
8.a Secondary CH2 refined with riding coordinates:
 C2A(H2AA,H2AB), C2B(H2BA,H2BB)
8.b Aromatic/amide H refined with riding coordinates:
 C4A(H4A), C5A(H5A), C7A(H7A), C8A(H8A), C10A(H10A), C11A(H11A), C13A(H13A),
 C14A(H14A), C16A(H16A), C17A(H17A), C18A(H18A), C19A(H19A), C20A(H20A),
 C4B(H4B), C5B(H5B), C7B(H7B), C8B(H8B), C10B(H10B), C11B(H11B), C13B(H13B),
 C14B(H14B), C16B(H16B), C17B(H17B), C18B(H18B), C19B(H19B), C20B(H20B)
;
_shelx_res_checksum              48897
_shelx_hkl_checksum              80374
_olex2_submission_special_instructions 'No special instructions were received'