Difluorenoheteroles: topological control of π conjugation in diradicaloids and mixed-valence radical ions
Prajapati, Bibek; Kwenda, Tendai; Lis, Tadeusz; Chmielewski, Piotr J.; Gómez-García, Carlos J.; Majewski, Marcin A.; Stępień, Marcin; Chemical Science 15 (2024) 10101–10109; doi:10.1039/D4SC02459A

data_1571708
_publ_section_title
;
 Difluorenoheteroles: topological control of \p conjugation in
 diradicaloids and mixed-valence radical ions
;
_journal_issue                   26
_journal_name_full               'Chemical Science'
_journal_page_first              10101
_journal_page_last               10109
_journal_paper_doi               10.1039/D4SC02459A
_journal_volume                  15
_journal_year                    2024
_chemical_formula_moiety         'C60 H67 N'
_chemical_formula_sum            'C60 H67 N'
_chemical_formula_weight         802.14
_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     direct
_audit_creation_date             2023-06-28
_audit_creation_method
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_audit_update_record
;
2023-10-22 deposited with the CCDC.	2024-05-21 downloaded from the CCDC.
;
_cell_angle_alpha                105.22(4)
_cell_angle_beta                 91.86(4)
_cell_angle_gamma                99.67(3)
_cell_formula_units_Z            2
_cell_length_a                   9.141(2)
_cell_length_b                   16.305(4)
_cell_length_c                   16.996(5)
_cell_measurement_reflns_used    9733
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      50
_cell_measurement_theta_min      2.7
_cell_volume                     2401.8(12)
_computing_cell_refinement       'CrysAlisPro 1.171.42.72a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.72a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.72a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            'HyPix-Arc 150'
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.944
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix-Arc 150'
_diffrn_measurement_method       'omega scan'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0560
_diffrn_reflns_av_unetI/netI     0.0713
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.944
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            31595
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.944
_diffrn_reflns_theta_full        67.000
_diffrn_reflns_theta_max         74.412
_diffrn_reflns_theta_min         2.703
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.467
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.600
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.72a (Rigaku Oxford Diffraction, 2022)
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            red-pink
_exptl_crystal_density_diffrn    1.109
_exptl_crystal_description       needle
_exptl_crystal_F_000             868
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.013
_refine_diff_density_max         0.438
_refine_diff_density_min         -0.492
_refine_diff_density_rms         0.092
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     567
_refine_ls_number_reflns         9269
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.1595
_refine_ls_R_factor_gt           0.1176
_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^)+(0.0776P)^2^+17.5749P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3186
_refine_ls_wR_factor_ref         0.3408
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5899
_reflns_number_total             9269
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4sc02459a3.cif
_cod_data_source_block           tw044a
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_atom_sites_solution_primary' value 'direct methods' was
changed to 'direct'.

Automatic conversion script
Id: cif_fix_values 8170 2020-07-09 18:12:32Z antanas 

 Adding full bibliography for 1571707--1571709.cif.
;
_cod_database_code               1571708
_shelxl_version_number           2013-2
_shelx_estimated_absorpt_t_max   0.994
_shelx_estimated_absorpt_t_min   0.835
_olex2_refinement_description
;
1. Shared sites
{C23A, C23C}
2. Uiso/Uaniso restraints and constraints
Uanis(C23A) = Uanis(C23C)
3. Others
 Sof(C23C)=Sof(H23C)=Sof(C25C)=Sof(H25G)=Sof(H25H)=Sof(H25I)=1-FVAR(1)
 Sof(C23A)=Sof(H23A)=Sof(C25A)=Sof(H25A)=Sof(H25B)=Sof(H25C)=FVAR(1)
4.a Ternary CH refined with riding coordinates:
 C20A(H20A), C23A(H23A), C23C(H23C), C26A(H26A), C20B(H20B), C23B(H23B),
 C26B(H26B)
4.b Secondary CH2 refined with riding coordinates:
 C1(H11,H12), C2(H21,H22), C3(H31,H32)
4.c Me refined with riding coordinates:
 C24A(H24A,H24B,H24C), C25C(H25G,H25H,H25I)
4.d Aromatic/amide H refined with riding coordinates:
 C3A(H3A), C6A(H6A), C8A(H8A), C9A(H9A), C10A(H10A), C11A(H11A), C16A(H16A),
 C18A(H18A), C3B(H3B), C6B(H6B), C8B(H8B), C9B(H9B), C10B(H10B), C11B(H11B),
 C16B(H16B), C18B(H18B)
4.e Idealised Me refined as rotating group:
 C21A(H21A,H21B,H21C), C22A(H22A,H22B,H22C), C25A(H25A,H25B,H25C), C27A(H27A,
 H27B,H27C), C28A(H28A,H28B,H28C), C21B(H21D,H21E,H21F), C22B(H22D,H22E,H22F),
 C24B(H24D,H24E,H24F), C25B(H25D,H25E,H25F), C27B(H27D,H27E,H27F), C28B(H28D,
 H28E,H28F), C4(H41,H42,H43)
;
_shelx_res_checksum              64360
_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 1.732
_oxdiff_exptl_absorpt_empirical_full_min 0.685