BNB-doped phenalenyls - aromaticity switch upon one-electron reduction.
Crumbach, Merian; Ayhan, Ozan; Fritze, Lars; Sprenger, Jan A. P.; Zapf, Ludwig; Finze, Maik; Helten, Holger; Chemical communications (Cambridge, England) 57 (2021) 2408–2411; doi:10.1039/d0cc07671f

data_7127893
_publ_section_title
;
 BNB-doped phenalenyls - aromaticity switch upon one-electron reduction.
;
_journal_issue                   19
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              2408
_journal_page_last               2411
_journal_paper_doi               10.1039/d0cc07671f
_journal_volume                  57
_journal_year                    2021
_chemical_formula_moiety         'C31 H17 B2 F18 N, 0.46(C1 H1 Cl3)'
_chemical_formula_sum            'C31.45 H17.45 B2 Cl1.36 F18 N O0'
_chemical_formula_weight         821.34
_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'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2020-09-10
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-09-10 deposited with the CCDC.	2021-01-27 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 100.5340(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   20.0781(7)
_cell_length_b                   7.6006(3)
_cell_length_c                   22.0644(7)
_cell_measurement_reflns_used    9970
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25.88
_cell_measurement_theta_min      2.52
_cell_volume                     3310.4(2)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_collection       'APEX3 v2018.7-2 (Bruker AXS)'
_computing_data_reduction        'SAINT V8.38A (?, 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    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100.15
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0374
_diffrn_reflns_av_unetI/netI     0.0290
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            38342
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         26.750
_diffrn_reflns_theta_min         1.878
_diffrn_source                   'rotating-anode X-ray tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.273
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6988
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1135 before and 0.0467 after correction. The Ratio of minimum to maximum transmission is 0.9375. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.648
_exptl_crystal_description       block
_exptl_crystal_F_000             1633
_exptl_crystal_size_max          0.407
_exptl_crystal_size_mid          0.213
_exptl_crystal_size_min          0.15
_refine_diff_density_max         1.366
_refine_diff_density_min         -0.731
_refine_diff_density_rms         0.077
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     557
_refine_ls_number_reflns         7036
_refine_ls_number_restraints     327
_refine_ls_restrained_S_all      1.281
_refine_ls_R_factor_all          0.0860
_refine_ls_R_factor_gt           0.0663
_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^)+(0.0716P)^2^+7.2041P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1653
_refine_ls_wR_factor_ref         0.1801
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5352
_reflns_number_total             7036
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0cc07671f2.cif
_cod_data_source_block           test_a
_cod_depositor_comments
'Adding full bibliography for 7127892--7127893.cif.'
_cod_database_code               7127893
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.960
_shelx_estimated_absorpt_t_min   0.897
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Shared sites
{C1, C11}
3. Restrained distances
 C1_6-Cl1_6 \\sim C1_6-Cl2_6 \\sim C1_6-Cl3_6
 with sigma of 0.02
 Cl1_6-Cl2_6 \\sim Cl2_6-Cl3_6 \\sim Cl3_6-Cl1_6
 with sigma of 0.04
 C8_4-F4_4 \\sim C8_4-C8_4 \\sim F5_4-C8_4 \\sim C8_4-F6_4 \\sim C8_4-?
 C8_5-F4_5 \\sim C8_5-F41_5 \\sim C8_5-F5_5 \\sim C8_5-F51_5 \\sim C8_5-F6_5
\\sim C8_5-F61_5
 with sigma of 0.01
 F4_4-F5_4 \\sim F4_4-F6_4 \\sim F5_4-F6_4
 F4_5-F5_5 \\sim F4_5-F6_5 \\sim F5_5-F6_5 \\sim F41_5-F51_5 \\sim F41_5-F61_5
\\sim F51_5-F61_5
 with sigma of 0.02
4. Rigid bond restraints
 F4_5, F5_5, F6_5, F41_5, F51_5, F61_5
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
5. Uiso/Uaniso restraints and constraints
All non-hydrogen atoms have similar U: within 1A with sigma of 0.04 and sigma
for terminal atoms of 0.08
F4_5 \\sim F5_5 \\sim F6_5 \\sim F41_5 \\sim F51_5 \\sim F61_5: within 2A with
sigma of 0.003 and sigma for terminal atoms of 0.006
C1_3 \\sim C2_3 \\sim C3_3 \\sim C11_3 \\sim C21_3 \\sim C31_3: within 2A with
sigma of 0.003 and sigma for terminal atoms of 0.006
C1_6 \\sim Cl1_6 \\sim Cl2_6 \\sim Cl3_6: within 2A with sigma of 0.003 and
sigma for terminal atoms of 0.006
Uanis(F4_5) \\sim Ueq, Uanis(F5_5) \\sim Ueq, Uanis(F6_5) \\sim Ueq,
Uanis(F41_5) \\sim Ueq, Uanis(F51_5) \\sim Ueq, Uanis(F61_5) \\sim Ueq: with
sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(C1_3) \\sim Ueq, Uanis(C2_3) \\sim Ueq, Uanis(C3_3) \\sim Ueq,
Uanis(C11_3) \\sim Ueq, Uanis(C21_3) \\sim Ueq, Uanis(C31_3) \\sim Ueq: with
sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(C1_6) \\sim Ueq, Uanis(Cl1_6) \\sim Ueq, Uanis(Cl2_6) \\sim Ueq,
Uanis(Cl3_6) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(C1_3) = Uanis(C11_3)
6. Rigid body (RIGU) restrains
 C1_6, Cl1_6, Cl2_6, Cl3_6
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 F4_5, F5_5, F6_5, F41_5, F51_5, F61_5
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C1_3, C2_3, C3_3, C11_3, C21_3, C31_3
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C1_6, Cl1_6, Cl2_6, Cl3_6
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
7. Same fragment restrains
8. Others
 Sof(F41)=Sof(F51)=Sof(F61)=1-FVAR(1)
 Sof(F4)=Sof(F5)=Sof(F6)=FVAR(1)
 Sof(C11)=Sof(H11)=Sof(C21)=Sof(H21A)=Sof(H21B)=Sof(H21C)=Sof(C31)=Sof(H31A)=
 Sof(H31B)=Sof(H31C)=1-FVAR(2)
 Sof(C1)=Sof(H1)=Sof(C2)=Sof(H2A)=Sof(H2B)=Sof(H2C)=Sof(C3)=Sof(H3A)=Sof(H3B)=
 Sof(H3C)=FVAR(2)
 Sof(C1)=Sof(H1)=Sof(Cl1)=Sof(Cl2)=Sof(Cl3)=FVAR(3)
9.a Ternary CH refined with riding coordinates:
 C1(H1), C11(H11), C1(H1)
9.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C6(H6), C7(H7), C8(H8), C3(H3), C5(H5), C3(H3), C5(H5)
9.c Idealised Me refined as rotating group:
 C2(H2A,H2B,H2C), C3(H3A,H3B,H3C), C21(H21A,H21B,H21C), C31(H31A,H31B,H31C)
;
_shelx_res_checksum              95664
_shelx_hkl_checksum              75603
_olex2_submission_special_instructions 'No special instructions were received'