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_4038741
_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         'C24 H14 Br O3, B F4'
_chemical_formula_sum            'C24 H14 B Br F4 O3'
_chemical_formula_weight         517.07
_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     dual
_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                91.724(4)
_cell_angle_beta                 98.862(4)
_cell_angle_gamma                116.907(6)
_cell_formula_units_Z            2
_cell_length_a                   8.8561(5)
_cell_length_b                   9.3777(5)
_cell_length_c                   14.1453(5)
_cell_measurement_reflns_used    3314
_cell_measurement_temperature    290.56(10)
_cell_measurement_theta_max      73.1460
_cell_measurement_theta_min      5.3010
_cell_volume                     1028.42(11)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_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    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      290.56(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4679
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
--------------------------------------------------------------------------
  1  \w      2.00  62.00   1.00    1.00    --   37.44 -99.00 150.00   60
  2  \w     32.00 144.00   1.00    1.00    --  110.40 -61.00 150.00  112
  3  \w     67.00 112.00   1.00    1.00    --  110.40-111.00  30.00   45
  4  \w     75.00 107.00   1.00    1.00    --  110.40-111.00 -90.00   32
  5  \w     83.00 108.00   1.00    1.00    --  110.40-111.00-180.00   25
  6  \w     38.00 139.00   1.00    1.00    --  110.40 -61.00 -90.00  101
  7  \w     93.00 169.00   1.00    1.00    --  110.40  61.00-150.00   76
  8  \w    138.00 178.00   1.00    1.00    --  110.40  77.00-120.00   40
  9  \w     91.00 118.00   1.00    1.00    --  110.40  77.00-120.00   27
 10  \w     67.00  93.00   1.00    1.00    --  110.40 178.00  60.00   26
 11  \w    125.00 150.00   1.00    1.00    --  110.40 178.00  60.00   25
 12  \w     97.00 129.00   1.00    1.00    --   37.44 178.00  90.00   32
 13  \w     23.00 174.00   1.00    1.00    --  110.40   0.00-150.00  151
 14  \w     32.00 125.00   1.00    1.00    --  110.40 -77.00  60.00   93
 15  \w     32.00  57.00   1.00    1.00    --  110.40-111.00  30.00   25
 16  \w     31.00  58.00   1.00    1.00    --  110.40-111.00-180.00   27
 17  \w   -105.00 -20.00   1.00    1.00    --  -37.44 -57.00  30.00   85
 18  \w   -116.00  -8.00   1.00    1.00    --  -37.44 -38.00 -90.00  108
 19  \w   -128.00 -41.00   1.00    1.00    --  -37.44-178.00 120.00   87
 20  \w    -74.00 -40.00   1.00    1.00    --  -37.44 178.00  60.00   34
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0024079000
_diffrn_orient_matrix_UB_12      0.1333011000
_diffrn_orient_matrix_UB_13      -0.0603015000
_diffrn_orient_matrix_UB_21      0.1966796000
_diffrn_orient_matrix_UB_22      0.0734607000
_diffrn_orient_matrix_UB_23      0.0073187000
_diffrn_orient_matrix_UB_31      -0.0275769000
_diffrn_orient_matrix_UB_32      -0.1058944000
_diffrn_orient_matrix_UB_33      -0.0928318000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0168
_diffrn_reflns_av_unetI/netI     0.0243
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            6622
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.466
_diffrn_reflns_theta_min         3.182
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    3.289
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79381
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
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    1.670
_exptl_crystal_description       block
_exptl_crystal_F_000             516
_exptl_crystal_size_max          0.291
_exptl_crystal_size_mid          0.168
_exptl_crystal_size_min          0.109
_refine_diff_density_max         0.533
_refine_diff_density_min         -0.480
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     335
_refine_ls_number_reflns         4003
_refine_ls_number_restraints     93
_refine_ls_restrained_S_all      1.207
_refine_ls_R_factor_all          0.0397
_refine_ls_R_factor_gt           0.0347
_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^)+(0.0500P)^2^+0.5389P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0917
_refine_ls_wR_factor_ref         0.0959
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3581
_reflns_number_total             4003
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo0c01716_si_002.cif
_cod_data_source_block           8B
_cod_depositor_comments
'Adding full bibliography for 4038740--4038746.cif.'
_cod_original_cell_volume        1028.42(10)
_cod_database_code               4038741
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C24 H14 B1 Br1 F4 O3'
_reflns_odcompleteness_completeness 99.70
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     67.29
_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. Restrained distances
 B1-F1A \\sim B1-F2A \\sim B1-F3A \\sim B1-F4A
 with sigma of 0.02
 F1A-F2A \\sim F1A-F3A \\sim F1A-F4A \\sim F2A-F3A \\sim F2A-F4A \\sim F3A-F4A
 with sigma of 0.04
 F4B-F2B \\sim F1B-F2B \\sim F1B-F3B \\sim F1B-F4B \\sim F2B-F4B \\sim F2B-F4B
 with sigma of 0.04
 B1-F3B \\sim B1-F4B \\sim B1-F1B \\sim B1-F2B
 with sigma of 0.02
3. Rigid body (RIGU) restrains
 F1A, F2A, F3A, F4A, B1
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 F1B, F2B, F3B, F4B, B1
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4. Others
 Fixed Sof: F1A(0.54295) F1B(0.45705) F2A(0.54295) F2B(0.45705) F3A(0.54295)
 F3B(0.45705) F4A(0.54295) F4B(0.45705)
5.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C7(H7), C8(H8), C9(H9), C13(H13), C14(H14), C15(H15),
 C23(H23), C24(H24), C25(H25)
5.b Idealised Me refined as rotating group:
 C28(H28A,H28B,H28C)
;
_shelx_res_checksum              79647
_shelx_hkl_checksum              98272
_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 1.228
_oxdiff_exptl_absorpt_empirical_full_min 0.832