Modulating the ground state, stability and charge transport in OFETs of biradicaloid Hexahydro-diindenopyrene derivatives and a proposed method to estimate the biradical character
Jousselin-Oba, Tanguy; Mamada, Masashi; Okazawa, Atsushi; Marrot, Jérome; Ishida, Takayuki; Adachi, Chihaya; Yassar, Abderrahim; Frigoli, Michel; Chemical Science  (2020) –; doi:10.1039/D0SC04583G

data_1559102
_publ_section_title
;
 Modulating the ground state, stability and charge transport in OFETs of
 biradicaloid Hexahydro-diindenopyrene derivatives and a proposed method
 to estimate the biradical character
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D0SC04583G
_journal_year                    2020
_chemical_formula_moiety         'C60 H66 Si2'
_chemical_formula_sum            'C60 H66 Si2'
_chemical_formula_weight         843.30
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-09-25
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-03-02 deposited with the CCDC.	2020-09-15 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 91.995(4)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.1631(3)
_cell_length_b                   13.8454(6)
_cell_length_c                   21.1693(8)
_cell_measurement_reflns_used    7081
_cell_measurement_temperature    123
_cell_measurement_theta_max      31.1090
_cell_measurement_theta_min      2.3590
_cell_volume                     2391.13(16)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_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      123
_diffrn_detector                 'Rigaku HyPix-6000 area detector'
_diffrn_detector_area_resol_mean 10.0
_diffrn_detector_type            'HPC area detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -23.00  73.00   0.50  120.00    --  -10.00  45.00   0.00  192
  2  \w    -80.00  71.00   0.50  120.00    --  -10.00  45.00 120.00  302
  3  \w    -98.00 -51.00   0.50  120.00    --  -10.00  45.00   0.00   94
;
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Rigaku AFC HyPix-6000'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0063090000
_diffrn_orient_matrix_UB_12      -0.0433339000
_diffrn_orient_matrix_UB_13      -0.0178638000
_diffrn_orient_matrix_UB_21      0.0739369000
_diffrn_orient_matrix_UB_22      -0.0168557000
_diffrn_orient_matrix_UB_23      0.0147199000
_diffrn_orient_matrix_UB_31      -0.0453633000
_diffrn_orient_matrix_UB_32      -0.0216057000
_diffrn_orient_matrix_UB_33      0.0241961000
_diffrn_radiation_monochromator  'multi-layer mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0344
_diffrn_reflns_av_unetI/netI     0.0365
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            21124
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.483
_diffrn_reflns_theta_min         2.423
_diffrn_source                   'rotating anode X-ray generator'
_diffrn_source_type              FR-E+
_exptl_absorpt_coefficient_mu    0.113
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.85036
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            blue
_exptl_crystal_colour_primary    blue
_exptl_crystal_density_diffrn    1.171
_exptl_crystal_description       needle
_exptl_crystal_F_000             908
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.369
_refine_diff_density_min         -0.264
_refine_diff_density_rms         0.045
_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     286
_refine_ls_number_reflns         5474
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0587
_refine_ls_R_factor_gt           0.0421
_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^)+(0.0465P)^2^+0.9999P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0971
_refine_ls_wR_factor_ref         0.1027
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4380
_reflns_number_total             5474
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0sc04583g2.cif
_cod_data_source_block           opera1909e
_cod_original_cell_volume        2391.13(18)
_cod_database_code               1559102
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C11 H10 N O'
_shelx_estimated_absorpt_t_max   0.999
_shelx_estimated_absorpt_t_min   0.967
_reflns_odcompleteness_completeness 99.79
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.42
_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.a Ternary CH refined with riding coordinates:
 C28(H28), C23(H23), C25(H25)
2.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C5(H5A,H5B), C6(H6A,H6B)
2.c Aromatic/amide H refined with riding coordinates:
 C17(H17), C11(H11), C14(H14), C15(H15), C12(H12), C16(H16)
2.d Idealised Me refined as rotating group:
 C30(H30A,H30B,H30C), C24(H24A,H24B,H24C), C27(H27A,H27B,H27C), C29(H29A,H29B,
 H29C), C31(H31A,H31B,H31C), C26(H26A,H26B,H26C)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.207
_oxdiff_exptl_absorpt_empirical_full_min 0.810