Functionalized cationic [4]helicenes with unique tuning of absorption, fluorescence and chiroptical properties up to the far-red range
Delgado, I. Hernández; Pascal, S.; Wallabregue, A.; Duwald, R.; Besnard, C.; Guénée, L.; Nançoz, C.; Vauthey, E.; Tovar, R. C.; Lunkley, J. L.; Muller, G.; Lacour, J.; Chem. Sci. 7 (2016) 4685–; doi:10.1039/C6SC00614K

data_1543067
_publ_section_title
;
 Functionalized cationic [4]helicenes with unique tuning of absorption,
 fluorescence and chiroptical properties up to the far-red range
;
_journal_issue                   7
_journal_name_full               'Chem. Sci.'
_journal_page_first              4685
_journal_paper_doi               10.1039/C6SC00614K
_journal_volume                  7
_journal_year                    2016
_chemical_formula_moiety         'B F4, C27 H30 N3 O2'
_chemical_formula_sum            'C27 H30 B F4 N3 O2'
_chemical_formula_weight         515.35
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2015-10-02
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_audit_update_record
;
2015-12-21 deposited with the CCDC.
2016-04-08 downloaded from the CCDC.
;
_cell_angle_alpha                67.020(5)
_cell_angle_beta                 84.303(4)
_cell_angle_gamma                85.759(4)
_cell_formula_units_Z            2
_cell_length_a                   7.8922(4)
_cell_length_b                   12.0779(7)
_cell_length_c                   13.8862(7)
_cell_measurement_reflns_used    7631
_cell_measurement_temperature    180.00(14)
_cell_measurement_theta_max      73.4370
_cell_measurement_theta_min      4.1070
_cell_volume                     1211.69(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 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      180.00(14)
_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 0.977
_diffrn_measurement_details
;
  1 omega  -69.00    6.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -      -38.9365   57.0000    0.0000 75

  2 omega   61.00  131.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -       38.9365  178.0000 -180.0000 70

  3 omega   84.00  138.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      109.7499   61.0000  -60.0000 54

  4 omega  101.00  177.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      109.7499   30.0000  -90.0000 76

  5 omega  134.00  171.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      109.7499   45.0000 -180.0000 37

  6 omega   80.00  106.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      109.7499   45.0000 -180.0000 26

  7 omega   46.00   72.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      109.7499  -30.0000  -60.0000 26

  8 omega   35.00  136.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      109.7499  -77.0000  -90.0000 101

  9 omega   84.00  116.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      109.7499 -111.0000  -60.0000 32

 10 omega   61.00   93.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      109.7499  -45.0000   30.0000 32

 11 omega   47.00  103.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      109.7499 -111.0000   90.0000 56

 12 omega   44.00   88.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      109.7499  -30.0000  150.0000 44

 13 omega   27.00   98.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      109.7499  -94.0000  150.0000 71

 14 omega   33.00   80.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      109.7499  -30.0000    0.0000 47

 15 omega   31.00   70.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      109.7499 -111.0000  -60.0000 39

 16 omega   24.00   99.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      109.7499  -94.0000 -150.0000 75

 17 omega    8.00   83.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -       38.9365  -99.0000 -180.0000 75

 18 omega   80.00  159.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      109.7499   61.0000  -30.0000 79

 19 omega -116.00  -23.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -      -38.9365  -38.0000 -150.0000 93

 20 omega -113.00  -88.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -      -38.9365  -99.0000  -60.0000 25

 21 omega -123.00  -83.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -      -38.9365  -99.0000 -120.0000 40

 22 omega -120.00  -85.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -      -38.9365  -99.0000    0.0000 35

 23 omega  -33.00   -6.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -      -38.9365  -57.0000  -30.0000 27

 24 omega -101.00  -37.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -      -38.9365  -57.0000  -30.0000 64

 25 omega -117.00  -73.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -      -38.9365  -38.0000  120.0000 44

 26 omega  -67.00  -21.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -      -38.9365  -38.0000  120.0000 46

 27 omega   -3.00   22.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -       40.0000   95.0000 -126.7582 25

 28 omega    4.00   29.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -       44.0000   89.0000   74.3767 25

 29 omega    9.00   34.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -       48.0000   86.0000  -29.1239 25

 30 omega   19.00   44.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -       56.0000   82.0000  126.9793 25

 31 omega   19.00   44.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -       56.0000   80.0000 -156.1566 25

 32 omega   19.00   44.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -       56.0000   82.0000   15.0239 25

 33 omega   19.00   44.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -       56.0000   81.0000  104.7121 25

 34 omega   19.00   46.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -       56.0000   80.0000  -21.2220 27

 35 omega   26.00   51.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -       60.0000   75.0000   13.6535 25

 36 omega   30.00   83.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -       60.0000   75.0000  -79.2673 53

 37 omega   78.00  137.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -       60.0000   75.0000   13.6535 59

 38 omega   92.00  144.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -       64.0000   76.0000   41.8394 52

 39 omega   31.00   59.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -       64.0000   76.0000  168.8353 28

 40 omega   31.00   68.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -       64.0000   76.0000   41.8394 37

 41 omega   28.00   70.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -       64.0000   75.0000 -101.0912 42

 42 omega   32.00   58.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -       68.0000   77.0000  108.5172 26

 43 omega   32.00   58.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -       68.0000   76.0000 -140.1656 26

 44 omega   36.00   90.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -       72.0000   76.0000  138.2342 54

 45 omega   78.00  131.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      109.7499   61.0000   30.0000 53

 46 omega   74.00  100.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      109.7499   77.0000 -180.0000 26

 47 omega   79.00  106.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      109.7499   61.0000   60.0000 27

 48 omega  112.00  164.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      109.7499   77.0000  120.0000 52

 49 omega   75.00  106.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      109.7499   77.0000  120.0000 31

 50 omega  128.00  172.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      109.7499   77.0000  -60.0000 44

 51 omega   74.00  100.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      109.7499   77.0000  -60.0000 26

 52 omega   77.00  103.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      109.7499   61.0000    0.0000 26

 53 omega   77.00  103.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      109.7499   61.0000  -90.0000 26

 54 omega  106.00  137.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      109.7499   77.0000  150.0000 31

 55 omega   78.00  105.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      109.7499   77.0000  150.0000 27
;
_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      -0.0152973000
_diffrn_orient_matrix_UB_12      -0.0681516000
_diffrn_orient_matrix_UB_13      0.1200226000
_diffrn_orient_matrix_UB_21      -0.1808636000
_diffrn_orient_matrix_UB_22      -0.0360882000
_diffrn_orient_matrix_UB_23      -0.0055447000
_diffrn_orient_matrix_UB_31      0.0747608000
_diffrn_orient_matrix_UB_32      -0.1151886000
_diffrn_orient_matrix_UB_33      -0.0131948000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0305
_diffrn_reflns_av_unetI/netI     0.0298
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            15168
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.395
_diffrn_reflns_theta_min         3.467
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.926
_exptl_absorpt_correction_T_max  0.988
_exptl_absorpt_correction_T_min  0.908
_exptl_absorpt_correction_type   gaussian
_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)
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            green
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.412
_exptl_crystal_description       plate
_exptl_crystal_F_000             540
_exptl_crystal_size_max          0.1245
_exptl_crystal_size_mid          0.1109
_exptl_crystal_size_min          0.0131
_refine_diff_density_max         0.226
_refine_diff_density_min         -0.258
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.960
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     346
_refine_ls_number_reflns         4747
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.960
_refine_ls_R_factor_all          0.0566
_refine_ls_R_factor_gt           0.0403
_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^)+(0.0410P)^2^+0.6270P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0904
_refine_ls_wR_factor_ref         0.0977
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3681
_reflns_number_total             4747
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6sc00614k2.cif
_cod_data_source_block           ih212c
_cod_depositor_comments
'Adding full bibliography for 1543067--1543076.cif.'
_cod_database_code               1543067
_chemical_oxdiff_formula         'C27 H30 B1 F4 N3 O2'
_chemical_oxdiff_usercomment     'C20 '
_reflns_odcompleteness_completeness 99.95
_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:
 C10(H10A,H10B), C25(H25A,H25B), C11(H11A,H11B), C24(H24A,H24B)
2.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C6(H6), C29(H29), C16(H16), C28(H28), C30(H30), C17(H17), C5(H5)
2.c Idealised Me refined as rotating group:
 C33(H33A,H33B,H33C), C1(H1A,H1B,H1C), C26(H26A,H26B,H26C), C12(H12A,H12B,H12C)
;
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'