Synthesis, Resolution, Configurational Stability, and Properties of Cationic Functionalized [5]Helicenes.
Marinova, Maya; Pascal, Simon; Guénée, Laure; Besnard, Céline; Shivachev, Boris; Kostova, Kalina; Villani, Claudio; Franzini, Roberta; Dimitrov, Vladimir; Lacour, Jérôme; The Journal of organic chemistry 85 (2020) 11908–11923; doi:10.1021/acs.joc.0c01716

data_4038742
_publ_section_title
;
 Synthesis, Resolution, Configurational Stability, and Properties of
 Cationic Functionalized [5]Helicenes.
;
_journal_issue                   18
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              11908
_journal_page_last               11923
_journal_paper_doi               10.1021/acs.joc.0c01716
_journal_volume                  85
_journal_year                    2020
_chemical_formula_moiety         'C29 H26 Br N2, B F4'
_chemical_formula_sum            'C29 H26 B Br F4 N2'
_chemical_formula_weight         569.24
_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             2020-02-28
_audit_creation_method
;
Olex2 1.3
(compiled Nov 21 2019 18:26:39 for OlexSys, GUI svn.r6003)
;
_cell_angle_alpha                77.279(4)
_cell_angle_beta                 80.071(3)
_cell_angle_gamma                80.432(3)
_cell_formula_units_Z            4
_cell_length_a                   12.7765(3)
_cell_length_b                   16.0668(6)
_cell_length_c                   17.3836(7)
_cell_measurement_reflns_used    9644
_cell_measurement_temperature    179.95(10)
_cell_measurement_theta_max      73.5220
_cell_measurement_theta_min      4.0650
_cell_volume                     3398.1(2)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      179.95(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4679
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.965
_diffrn_measurement_details
;
  1 omega -121.00  -83.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -      -41.3966  -99.0000   60.0000 38

  2 omega  -67.00   26.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -      -41.3966   57.0000  -60.0000 93

  3 omega -123.00  -79.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -      -41.3966  -99.0000 -150.0000 44

  4 omega -118.00  -90.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -      -41.3966  -99.0000  -60.0000 28

  5 omega -124.00  -82.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -      -41.3966  -99.0000    0.0000 42

  6 omega -123.00  -79.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -      -41.3966  -99.0000  -90.0000 44

  7 omega   31.00   78.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -       41.3966 -125.0000   30.0000 47

  8 omega   25.00   60.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -       41.3966 -125.0000 -120.0000 35

  9 omega   15.00   86.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -       41.3966 -105.0000   93.0000 71

 10 omega   32.00   97.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      108.5399  -94.0000  -60.0000 65

 11 omega   76.00  107.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      108.5399  -94.0000  120.0000 31

 12 omega   51.00   88.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      108.5399  -45.0000  -90.0000 37

 13 omega   56.00   85.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      108.5399  -94.0000 -120.0000 29

 14 omega   35.00  122.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      108.5399 -125.0000   60.0000 87

 15 omega   92.00  175.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      108.5399   45.0000 -150.0000 83

 16 omega   41.00  104.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      108.5399  -94.0000 -150.0000 63

 17 omega   36.00   88.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      108.5399  -30.0000   30.0000 52

 18 omega   31.00   80.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      108.5399  -30.0000 -180.0000 49

 19 omega   39.00   99.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      108.5399  -45.0000   90.0000 60

 20 omega   32.00  115.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      108.5399  -77.0000   30.0000 83

 21 omega   30.00  153.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      108.5399  -15.0000 -150.0000 123
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0057334000
_diffrn_orient_matrix_UB_12      0.0430989000
_diffrn_orient_matrix_UB_13      0.0717662000
_diffrn_orient_matrix_UB_21      -0.0315435000
_diffrn_orient_matrix_UB_22      0.0885516000
_diffrn_orient_matrix_UB_23      -0.0520421000
_diffrn_orient_matrix_UB_31      -0.1192837000
_diffrn_orient_matrix_UB_32      -0.0117787000
_diffrn_orient_matrix_UB_33      0.0237312000
_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  0.0493
_diffrn_reflns_av_unetI/netI     0.0556
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.965
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            23721
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.965
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.015
_diffrn_reflns_theta_min         3.475
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.978
_exptl_absorpt_correction_T_max  0.965
_exptl_absorpt_correction_T_min  0.640
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
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    1.113
_exptl_crystal_description       plate
_exptl_crystal_F_000             1160
_exptl_crystal_size_max          0.3395
_exptl_crystal_size_mid          0.2228
_exptl_crystal_size_min          0.0181
_refine_diff_density_max         1.150
_refine_diff_density_min         -1.182
_refine_diff_density_rms         0.067
_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     671
_refine_ls_number_reflns         13315
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0720
_refine_ls_R_factor_gt           0.0619
_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^)+(0.1127P)^2^+0.6752P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1771
_refine_ls_wR_factor_ref         0.1909
_reflns_Friedel_coverage         0.000
_reflns_number_gt                10718
_reflns_number_total             13315
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo0c01716_si_002.cif
_cod_data_source_block           9A
_cod_depositor_comments
'Adding full bibliography for 4038740--4038746.cif.'
_cod_original_cell_volume        3398.0(2)
_cod_database_code               4038742
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C58 H52 B2 Br2 F8 N4'
_reflns_odcompleteness_completeness 99.91
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 Secondary CH2 refined with riding coordinates:
 C24A(H24A,H24B), C25A(H25A,H25B), C13A(H13A,H13B), C14A(H14A,H14B), C13B(H13C,
 H13D), C24B(H24C,H24D), C14B(H14C,H14D), C25B(H25C,H25D)
2.b Aromatic/amide H refined with riding coordinates:
 C29A(H29A), C3A(H3A), C7A(H7A), C20A(H20A), C21A(H21A), C9A(H9A), C30A(H30A),
 C4A(H4A), C8A(H8A), C19A(H19A), C28A(H28A), C31A(H31A), C31B(H31B), C21B(H21B),
  C28B(H28B), C29B(H29B), C20B(H20B), C7B(H7B), C30B(H30B), C9B(H9B), C3B(H3B),
 C8B(H8B), C19B(H19B), C4B(H4B)
2.c Idealised Me refined as rotating group:
 C26A(H26A,H26B,H26C), C15A(H15A,H15B,H15C), C26B(H26D,H26E,H26F), C15B(H15D,
 H15E,H15F)
;
_shelx_res_checksum              73738
_shelx_hkl_checksum              54033
_shelx_fab_checksum              57285
_platon_squeeze_special_details
;
The squeeze/bypass method was used to take care of 3 disordered toluene molecule
 per asymetric unit.
A solvent mask was calculated and 311 electrons were
found in a volume of 1133\%A^3 in 1 void per unit cell.
This is consistent with the presence of 
6[C7H8] per Unit Cell 
which account for 300 electrons 
per unit cell.
;
_platon_squeeze_void_probe_radius 1.20
_olex2_submission_special_instructions 'No special instructions were received'