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_1559100
_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, 2(C9 H12)'
_chemical_formula_sum            'C78 H90 Si2'
_chemical_formula_weight         1083.67
_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   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2020-02-26
_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                99.626(4)
_cell_angle_beta                 104.748(6)
_cell_angle_gamma                98.811(4)
_cell_formula_units_Z            1
_cell_length_a                   8.8789(6)
_cell_length_b                   12.7356(5)
_cell_length_c                   14.6701(9)
_cell_measurement_reflns_used    4693
_cell_measurement_temperature    100
_cell_measurement_theta_max      28.8930
_cell_measurement_theta_min      2.4180
_cell_volume                     1547.94(17)
_computing_cell_refinement       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_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      100
_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 0.995
_diffrn_measured_fraction_theta_max 0.983
_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    -75.00 -47.00   0.50   45.00    --    4.70  45.00  90.00   56
  2  \w    -39.00  83.00   0.50   45.00    --    4.70  45.00  90.00  244
  3  \w    -72.00  12.00   0.50   45.00    --    4.70  45.00  30.00  168
  4  \w     39.00  87.00   0.50   45.00    --    4.70  45.00  30.00   96
  5  \w    -31.00  64.00   0.50   45.00    --    4.70  45.00 150.00  190
;
_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      -0.0174465000
_diffrn_orient_matrix_UB_12      -0.0045327000
_diffrn_orient_matrix_UB_13      -0.0506184000
_diffrn_orient_matrix_UB_21      0.0088038000
_diffrn_orient_matrix_UB_22      0.0573170000
_diffrn_orient_matrix_UB_23      0.0068007000
_diffrn_orient_matrix_UB_31      0.0821128000
_diffrn_orient_matrix_UB_32      0.0050731000
_diffrn_orient_matrix_UB_33      0.0036526000
_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  0.0379
_diffrn_reflns_av_unetI/netI     0.0485
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            17632
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_min         2.441
_diffrn_source                   'rotating anode X-ray generator'
_diffrn_source_type              FR-E+
_exptl_absorpt_coefficient_mu    0.102
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.94583
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.67a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.163
_exptl_crystal_description       plate
_exptl_crystal_F_000             586
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.861
_refine_diff_density_min         -0.479
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     370
_refine_ls_number_reflns         6212
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0803
_refine_ls_R_factor_gt           0.0585
_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^)+(0.0560P)^2^+1.5843P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1336
_refine_ls_wR_factor_ref         0.1435
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4914
_reflns_number_total             6212
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0sc04583g2.cif
_cod_data_source_block           opera2002a
_cod_original_cell_volume        1547.92(16)
_cod_database_code               1559100
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C11 H10 N O'
_chemical_oxdiff_usercomment     100K
_shelx_estimated_absorpt_t_max   0.999
_shelx_estimated_absorpt_t_min   0.990
_reflns_odcompleteness_completeness 98.28
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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:
 C00Q(H00Q), C00U(H00U), C00Z(H00Z)
2.b Secondary CH2 refined with riding coordinates:
 C00F(H00A,H00B), C00I(H00E,H00F), C00P(H00I,H00J)
2.c Aromatic/amide H refined with riding coordinates:
 C00C(H00C), C00D(H00D), C00G(H00G), C00H(H00H), C00L(H00L), C00M(H00M),
 C00N(H00X), C00O(H00Y), C00R(H00)
2.d Idealised Me refined as rotating group:
 C00T(H00K,H00N,H00O), C00W(H00P,H00R,H00S), C00X(H0AA,H,HA), C00Y(H00T,H00V,
 H00W), C010(H01J,H01K,H01L), C011(H01A,H01B,H01C), C012(H01M,H01N,H01O),
 C013(H01D,H01E,H01F), C014(H01G,H01H,H01I)
;
_shelx_res_checksum              43265
_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 1.100
_oxdiff_exptl_absorpt_empirical_full_min 0.908