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_4038746
_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         'C27 H22 Br N O2, C H2 Cl2'
_chemical_formula_sum            'C28 H24 Br Cl2 N O2'
_chemical_formula_weight         557.29
_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                110.420(6)
_cell_angle_beta                 95.401(5)
_cell_angle_gamma                112.560(6)
_cell_formula_units_Z            2
_cell_length_a                   9.9075(7)
_cell_length_b                   11.5025(7)
_cell_length_c                   12.5629(8)
_cell_measurement_reflns_used    5713
_cell_measurement_temperature    180.00(10)
_cell_measurement_theta_max      73.6600
_cell_measurement_theta_min      4.5540
_cell_volume                     1195.28(17)
_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      N~2~
_diffrn_ambient_temperature      180.00(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 0.961
_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   -104.00  -9.00   1.00    1.00    --  -37.56 -38.00 -90.00   95
  2  \w     57.00  85.00   1.00    1.00    --   37.56-178.00 -60.00   28
  3  \w     25.00  50.00   1.00    1.00    --  110.40 -94.00 -90.00   25
  4  \w     64.00 103.00   1.00    1.00    --  110.40 -94.00 -90.00   39
  5  \w     73.00 109.00   1.00    1.00    --  110.40 -94.00 -30.00   36
  6  \w     32.00 144.00   1.00    1.00    --  110.40 -30.00  90.00  112
  7  \w     89.00 132.00   1.00    1.00    --  110.40  61.00 -30.00   43
  8  \w    101.00 127.00   1.00    1.00    --  110.40 111.00  90.00   26
  9  \w     82.00 130.00   1.00    1.00    --   37.56 178.00   0.00   48
 10  \w     65.00 127.00   1.00    1.00    --   37.56 178.00-180.00   62
 11  \w     25.00 171.00   1.00    1.00    --  110.40 -15.00 -60.00  146
 12  \w     64.00 115.00   1.00    1.00    --  110.40-111.00 120.00   51
 13  \w     35.00 144.00   1.00    1.00    --  110.40 -61.00 -30.00  109
 14  \w     27.00  56.00   1.00    1.00    --  110.40 -77.00 -90.00   29
 15  \w     25.00  69.00   1.00    1.00    --  110.40 -94.00 -30.00   44
 16  \w     26.00 137.00   1.00    1.00    --  110.40 -77.00 120.00  111
 17  \w    -72.00 -34.00   1.00    1.00    --  -37.56 178.00 150.00   38
 18  \w    -94.00 -38.00   1.00    1.00    --  -37.56 178.00  60.00   56
 19  \w   -116.00  -6.00   1.00    1.00    --  -37.56 -57.00  30.00  110
;
_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      0.0900379000
_diffrn_orient_matrix_UB_12      0.1586920000
_diffrn_orient_matrix_UB_13      0.0477320000
_diffrn_orient_matrix_UB_21      -0.0014089000
_diffrn_orient_matrix_UB_22      -0.0129990000
_diffrn_orient_matrix_UB_23      -0.1264132000
_diffrn_orient_matrix_UB_31      -0.1495190000
_diffrn_orient_matrix_UB_32      0.0124672000
_diffrn_orient_matrix_UB_33      -0.0117723000
_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  0.0333
_diffrn_reflns_av_unetI/netI     0.0333
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.961
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            7481
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.961
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.642
_diffrn_reflns_theta_min         3.892
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    4.617
_exptl_absorpt_correction_T_max  0.364
_exptl_absorpt_correction_T_min  0.102
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.548
_exptl_crystal_description       prism
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.98
_exptl_crystal_size_mid          0.487
_exptl_crystal_size_min          0.351
_refine_diff_density_max         1.460
_refine_diff_density_min         -0.829
_refine_diff_density_rms         0.106
_refine_ls_extinction_coef       0.0204(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     310
_refine_ls_number_reflns         4648
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0509
_refine_ls_R_factor_gt           0.0496
_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^)+(0.0915P)^2^+0.7927P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1321
_refine_ls_wR_factor_ref         0.1338
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4448
_reflns_number_total             4648
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo0c01716_si_002.cif
_cod_data_source_block           24B
_cod_depositor_comments
'Adding full bibliography for 4038740--4038746.cif.'
_cod_original_cell_volume        1195.28(15)
_cod_database_code               4038746
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C28 H24 Br1 Cl2 N1 O2'
_reflns_odcompleteness_completeness 99.65
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     67.29
_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 Ternary CH refined with riding coordinates:
 C21(H21)
2.b Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C13(H13A,H13B), C31(H31A,H31B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C6(H6), C8(H8), C9(H9), C16(H16), C17(H17), C18(H18),
 C25(H25), C26(H26), C27(H27)
2.d Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C30(H30A,H30B,H30C)
;
_shelx_res_checksum              19080
_shelx_hkl_checksum              90763
_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 2.282
_oxdiff_exptl_absorpt_empirical_full_min 0.405