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_1571709
_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         802.207
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_Int_Tables_number      14
_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                90
_cell_angle_beta                 93.27(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.742(2)
_cell_length_b                   15.560(4)
_cell_length_c                   30.552(12)
_cell_measurement_reflns_used    7900
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      100
_cell_measurement_theta_min      2.8
_cell_volume                     4624(2)
_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  'olex2.refine 1.5 (Bourhis et al., 2015)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.15
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            'HyPix-Arc 150'
_diffrn_measured_fraction_theta_full 0.9979
_diffrn_measured_fraction_theta_max 0.9542
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix-Arc 150'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0940
_diffrn_reflns_av_unetI/netI     0.0914
_diffrn_reflns_Laue_measured_fraction_full 0.9979
_diffrn_reflns_Laue_measured_fraction_max 0.9542
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_number            32984
_diffrn_reflns_point_group_measured_fraction_full 0.9979
_diffrn_reflns_point_group_measured_fraction_max 0.9542
_diffrn_reflns_theta_full        67.0000
_diffrn_reflns_theta_max         74.48
_diffrn_reflns_theta_min         2.90
_exptl_absorpt_coefficient_mu    0.485
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.775
_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            green
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.152
_exptl_crystal_description       needle
_exptl_crystal_F_000             1740.737
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.5040
_refine_diff_density_min         -0.4800
_refine_diff_density_rms         0.1088
_refine_ls_d_res_high            0.8001
_refine_ls_d_res_low             15.2511
_refine_ls_goodness_of_fit_ref   1.0200
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    105
_refine_ls_number_parameters     563
_refine_ls_number_reflns         9022
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0200
_refine_ls_R_factor_all          0.1197
_refine_ls_R_factor_gt           0.0633
_refine_ls_shift/su_max          -0.0005
_refine_ls_shift/su_mean         0.0001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1034P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1556
_refine_ls_wR_factor_ref         0.1911
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              11
_reflns_limit_h_min              -12
_reflns_limit_k_max              19
_reflns_limit_k_min              0
_reflns_limit_l_max              37
_reflns_limit_l_min              -10
_reflns_number_gt                5296
_reflns_number_total             9022
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            d4sc02459a3.cif
_cod_data_source_block           tw043a
_cod_depositor_comments
'Adding full bibliography for 1571707--1571709.cif.'
_cod_database_code               1571709
_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:
 C27A(H27A), C28A(H28A), C29A(H29A), C27B(H27B), C28B(H28B), C29B(H29B)
2.b Secondary CH2 refined with riding coordinates:
 C1(H1a,H1b), C2(H2a,H2b), C3(H3a,H3b)
2.c Aromatic/amide H refined with riding coordinates:
 C3A(H3Aa), C7A(H7A), C8A(H8A), C9A(H9A), C10A(H10A), C13A(H13A), C23A(H23A),
 C25A(H25A), C3B(H3Ba), C7B(H7B), C8B(H8B), C9B(H9B), C10B(H10B), C13B(H13B),
 C23B(H23B), C25B(H25B)
2.d Idealised Me refined as rotating group:
 C4(H4a,H4b,H4c), C30A(H30a,H30b,H30c), C31A(H31a,H31b,H31c), C32A(H32a,H32b,
 H32c), C33A(H33a,H33b,H33c), C34A(H34a,H34b,H34c), C35A(H35a,H35b,H35c),
 C30B(H30d,H30e,H30f), C31B(H31d,H31e,H31f), C32B(H32d,H32e,H32f), C33B(H33d,
 H33e,H33f), C34B(H34d,H34e,H34f), C35B(H35d,H35e,H35f)
;
_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
;