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_4038745
_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 H28 Br N O4'
_chemical_formula_sum            'C29 H28 Br N O4'
_chemical_formula_weight         534.43
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2020-03-26
_audit_creation_method
;
Olex2 1.3
(compiled 2020.02.04 svn.rd84adfe8 for OlexSys, GUI svn.r6032)
;
_cell_angle_alpha                90
_cell_angle_beta                 99.059(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.9485(3)
_cell_length_b                   21.3763(5)
_cell_length_c                   13.2147(3)
_cell_measurement_reflns_used    10389
_cell_measurement_temperature    290
_cell_measurement_theta_max      26.0750
_cell_measurement_theta_min      3.1910
_cell_volume                     2496.25(12)
_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_temperature      290
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3974
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.915
_diffrn_measurement_details
;
  1 omega   35.00  101.00   1.0000   29.0000
omega____ theta____ kappa____ phi______ frames
    -       11.4169  178.0000  120.0000 66

  2 omega  -15.00   88.00   1.0000   29.0000
omega____ theta____ kappa____ phi______ frames
    -       11.4169   37.0000  -90.0000 103

  3 omega  -65.00   38.00   1.0000   29.0000
omega____ theta____ kappa____ phi______ frames
    -       11.4169  -37.0000   90.0000 103

  4 omega  -72.00  -27.00   1.0000   29.0000
omega____ theta____ kappa____ phi______ frames
    -      -11.8857  129.0000   -9.4106 45

  5 omega -100.00  -55.00   1.0000   29.0000
omega____ theta____ kappa____ phi______ frames
    -      -11.8857  178.0000  -90.0000 45

  6 omega  -20.00   30.00   1.0000   29.0000
omega____ theta____ kappa____ phi______ frames
    -      -11.8857  -99.0000    0.0000 50

  7 omega  -37.00   14.00   1.0000   29.0000
omega____ theta____ kappa____ phi______ frames
    -      -11.8857  -37.0000  150.0000 51

  8 omega  -15.00   21.00   1.0000   29.0000
omega____ theta____ kappa____ phi______ frames
    -      -11.8857  -99.0000  -90.0000 36

  9 omega  -75.00  -36.00   1.0000   29.0000
omega____ theta____ kappa____ phi______ frames
    -      -11.8857  -37.0000  -30.0000 39
;
_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      0.0144115000
_diffrn_orient_matrix_UB_12      -0.0306657000
_diffrn_orient_matrix_UB_13      -0.0165112000
_diffrn_orient_matrix_UB_21      0.0788799000
_diffrn_orient_matrix_UB_22      0.0062118000
_diffrn_orient_matrix_UB_23      0.0089800000
_diffrn_orient_matrix_UB_31      0.0042657000
_diffrn_orient_matrix_UB_32      -0.0110266000
_diffrn_orient_matrix_UB_33      0.0509899000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0367
_diffrn_reflns_av_unetI/netI     0.0296
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.915
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            35238
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.915
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.504
_diffrn_reflns_theta_min         2.980
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    1.683
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.67536
_exptl_absorpt_correction_type   multi-scan
_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)
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    1.422
_exptl_crystal_description       plate
_exptl_crystal_F_000             1104
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.566
_refine_diff_density_min         -0.725
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     324
_refine_ls_number_reflns         6364
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.0845
_refine_ls_R_factor_gt           0.0480
_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^)+(0.0408P)^2^+1.4883P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1038
_refine_ls_wR_factor_ref         0.1185
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4179
_reflns_number_total             6364
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo0c01716_si_002.cif
_cod_data_source_block           16B
_cod_depositor_comments
'Adding full bibliography for 4038740--4038746.cif.'
_cod_original_cell_volume        2496.26(12)
_cod_database_code               4038745
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C28 N1 O3 Br1'
_chemical_oxdiff_usercomment     'MMF1  Maya Kalina'
_shelx_estimated_absorpt_t_max   0.786
_shelx_estimated_absorpt_t_min   0.632
_reflns_odcompleteness_completeness 99.83
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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:
 C21(H21A,H21B), C25(H25A,H25B)
2.b Aromatic/amide H refined with riding coordinates:
 C13(H13), C17(H17), C19(H19), C22(H22), C23(H23), C24(H24), C26(H26),
 C27(H27), C28(H28), C29(H29), C31(H31)
2.c Idealised Me refined as rotating group:
 C30(H30A,H30B,H30C), C32(H32A,H32B,H32C), C33(H33A,H33B,H33C), C34(H34A,H34B,
 H34C)
;
_shelx_res_checksum              11756
_shelx_hkl_checksum              86743
_olex2_submission_special_instructions 'No special instructions were received'