Persistent, highly localized, and tunable [4]helicene radicals
Shaikh, Aslam C.; Moutet, Jules; Veleta, José M.; Hossain, Md Mubarak; Bloch, Jan; Astashkin, Andrei V.; Gianetti, Thomas L.; Chemical Science  (2020) –; doi:10.1039/D0SC04850J

data_1559174
_publ_section_title
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 Persistent, highly localized, and tunable [4]helicene radicals
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D0SC04850J
_journal_year                    2020
_chemical_formula_moiety         'B F4, C31 H38 N5 O4'
_chemical_formula_sum            'C31 H39 B F4 N5 O4'
_chemical_formula_weight         632.48
_chemical_name_common            2-NO2cation
_chemical_name_systematic        2-NO2cation
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-11-22
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-05-20 deposited with the CCDC.	2020-09-14 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 113.7260(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   22.4230(7)
_cell_length_b                   11.1591(4)
_cell_length_c                   26.6457(11)
_cell_measurement_reflns_used    9744
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      73.18
_cell_measurement_theta_min      3.92
_cell_volume                     6103.8(4)
_computing_cell_refinement       'SAINT V8.40A (?, 2016)'
_computing_data_reduction        'SAINT V8.40A (?, 2016)'
_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      100.0
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34138
_diffrn_reflns_av_R_equivalents  0.0371
_diffrn_reflns_av_unetI/netI     0.0215
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_number            72727
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         73.298
_diffrn_reflns_theta_min         3.923
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.582
_exptl_absorpt_correction_T_max  0.7537
_exptl_absorpt_correction_T_min  0.6401
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0834 before and 0.0551 after correction. The Ratio of minimum to maximum transmission is 0.8493. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            'metallic dark red'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.377
_exptl_crystal_description       plate
_exptl_crystal_F_000             2664
_exptl_crystal_recrystallization_method 'from acetonitrile ether layering'
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.337
_refine_diff_density_min         -0.271
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.965
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     412
_refine_ls_number_reflns         9160
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.965
_refine_ls_R_factor_all          0.0427
_refine_ls_R_factor_gt           0.0405
_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^)+(0.0610P)^2^+5.1492P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1094
_refine_ls_wR_factor_ref         0.1114
_reflns_Friedel_coverage         0.000
_reflns_number_gt                8589
_reflns_number_total             9160
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0sc04850j2.cif
_cod_data_source_block           2-NO2cation
_cod_database_code               1559174
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.977
_shelx_estimated_absorpt_t_min   0.955
_olex2_refinement_description
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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 Secondary CH2 refined with riding coordinates:
 C00Q(H00A,H00B), C00S(H00C,H00D), C00X(H00F,H00G), C00Z(H00H,H00I), C011(H01A,
 H01B), C012(H01C,H01D)
2.b Aromatic/amide H refined with riding coordinates:
 C00E(H00E), C00R(H00R), C00T(H00T), C00U(H00U), C00V(H00V), C00W(H00W),
 C00Y(H00Y), C010(H010)
2.c Idealised Me refined as rotating group:
 C013(H01E,H01F,H01G), C014(H01H,H01I,H01J), C015(H01K,H01L,H01M), C016(H01N,
 H01O,H01P), C017(H01Q,H01R,H01S), C018(H01T,H01U,H01V)
;
_shelx_res_checksum              95414
_olex2_submission_special_instructions 'No special instructions were received'