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_4038744
_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         'C23 H11 Br O3'
_chemical_formula_sum            'C23 H11 Br O3'
_chemical_formula_weight         415.23
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2020-03-30
_audit_creation_method
;
Olex2 1.3
(compiled 2020.02.04 svn.rd84adfe8 for OlexSys, GUI svn.r6032)
;
_cell_angle_alpha                90
_cell_angle_beta                 106.1860(17)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   20.2508(3)
_cell_length_b                   4.24318(7)
_cell_length_c                   19.0965(3)
_cell_measurement_reflns_used    2902
_cell_measurement_temperature    180.15
_cell_measurement_theta_max      73.3420
_cell_measurement_theta_min      4.5150
_cell_volume                     1575.88(4)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (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_temperature      180.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4679
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.967
_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    -62.00  20.00   1.00    1.00    --  -37.56  38.00-180.00   82
  2  \w   -115.00  -8.00   1.00    1.00    --  -37.56 -38.00   0.00  107
  3  \w    122.00 178.00   1.00    2.00    --  110.40 111.00   0.00   56
  4  \w    136.00 162.00   1.00    2.00    --  110.40 111.00 -30.00   26
  5  \w    107.00 150.00   1.00    2.00    --  110.40 178.00  90.00   43
  6  \w     79.00 173.00   1.00    2.00    --  110.40  45.00-150.00   94
  7  \w     50.00 141.00   1.00    2.00    --  110.40 -45.00-150.00   91
  8  \w     39.00 130.00   1.00    2.00    --  110.40 -30.00  30.00   91
  9  \w   -130.00-104.00   1.00    1.00    --  -37.56-178.00 150.00   26
;
_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      -0.0630334000
_diffrn_orient_matrix_UB_12      -0.0583078000
_diffrn_orient_matrix_UB_13      -0.0657349000
_diffrn_orient_matrix_UB_21      0.0455450000
_diffrn_orient_matrix_UB_22      0.0374649000
_diffrn_orient_matrix_UB_23      -0.0520022000
_diffrn_orient_matrix_UB_31      0.0150778000
_diffrn_orient_matrix_UB_32      -0.3564742000
_diffrn_orient_matrix_UB_33      0.0053168000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0152
_diffrn_reflns_av_unetI/netI     0.0222
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.967
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       3
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            4791
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.967
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.469
_diffrn_reflns_theta_min         4.547
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    3.753
_exptl_absorpt_correction_T_max  0.888
_exptl_absorpt_correction_T_min  0.340
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
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    1.750
_exptl_crystal_description       plate
_exptl_crystal_F_000             832
_exptl_crystal_size_max          0.625
_exptl_crystal_size_mid          0.171
_exptl_crystal_size_min          0.033
_refine_diff_density_max         0.368
_refine_diff_density_min         -0.659
_refine_diff_density_rms         0.067
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         3081
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.0337
_refine_ls_R_factor_gt           0.0300
_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^)+(0.0461P)^2^+0.9283P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0782
_refine_ls_wR_factor_ref         0.0817
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2772
_reflns_number_total             3081
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo0c01716_si_002.cif
_cod_data_source_block           15B
_cod_depositor_comments
'Adding full bibliography for 4038740--4038746.cif.'
_cod_original_cell_volume        1575.88(5)
_cod_database_code               4038744
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C23 H11 Br1 O3'
_reflns_odcompleteness_completeness 99.81
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C11(H11), C12(H12), C9(H9), C18(H18), C1(H1), C6(H6), C2(H2), C24(H24),
 C26(H26), C7(H7), C25(H25)
;
_shelx_res_checksum              48879
_shelx_hkl_checksum              26679
_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 1.428
_oxdiff_exptl_absorpt_empirical_full_min 0.543