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_1543073
_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         'C30 H33 N2 O3 S, C H2 Cl2, B F4'
_chemical_formula_sum            'C31 H35 B Cl2 F4 N2 O3 S'
_chemical_formula_weight         673.38
_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   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2015-03-31
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_audit_update_record
;
2015-12-21 deposited with the CCDC.
2016-04-08 downloaded from the CCDC.
;
_cell_angle_alpha                84.422(4)
_cell_angle_beta                 65.830(5)
_cell_angle_gamma                79.905(4)
_cell_formula_units_Z            2
_cell_length_a                   11.1714(6)
_cell_length_b                   11.8849(6)
_cell_length_c                   13.3323(7)
_cell_measurement_reflns_used    14776
_cell_measurement_temperature    180(2)
_cell_measurement_theta_max      73.5010
_cell_measurement_theta_min      4.3570
_cell_volume                     1589.32(16)
_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, 2008)'
_computing_structure_solution    'SIR2004 (Burla et al., 2007)'
_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 0.999
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_details
;
  1 omega -129.00   53.00   0.5000    0.5000
omega____ theta____ kappa____ phi______ frames
    -      -37.5615    0.0000  -90.0000 364

  2 omega  -67.00   -4.00   0.5000    0.5000
omega____ theta____ kappa____ phi______ frames
    -      -37.5615   57.0000  -90.0000 126

  3 omega   73.00   99.00   0.5000    0.5000
omega____ theta____ kappa____ phi______ frames
    -       37.5615  178.0000   90.0000 52

  4 omega   68.00  124.00   0.5000    0.5000
omega____ theta____ kappa____ phi______ frames
    -       37.5615  178.0000 -120.0000 112

  5 omega   66.00  105.00   0.5000    0.5000
omega____ theta____ kappa____ phi______ frames
    -       37.5615 -178.0000  150.0000 78

  6 omega   74.00  130.00   0.5000    0.5000
omega____ theta____ kappa____ phi______ frames
    -       37.5615  178.0000   60.0000 112

  7 omega   75.00  168.00   0.5000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      110.3999   30.0000  -30.0000 186

  8 omega   73.00  175.00   0.5000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      110.3999   30.0000 -120.0000 204

  9 omega   32.00   78.00   0.5000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      110.3999  -77.0000 -150.0000 92

 10 omega   47.00   87.00   0.5000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      110.3999  -30.0000 -180.0000 80

 11 omega   42.00   90.00   0.5000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      110.3999  -45.0000   30.0000 96

 12 omega   30.00   99.00   0.5000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      110.3999 -111.0000   30.0000 138

 13 omega   83.00  109.00   0.5000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      110.3999  -94.0000 -150.0000 52

 14 omega   34.00   83.00   0.5000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      110.3999  -30.0000   60.0000 98

 15 omega   32.00  109.00   0.5000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      110.3999 -111.0000 -150.0000 154

 16 omega   35.00   75.00   0.5000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      110.3999  -29.0000  -18.0000 80

 17 omega  142.00  178.00   0.5000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      110.3999  111.0000  -90.0000 72

 18 omega  102.00  136.00   0.5000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      110.3999  111.0000  150.0000 68

 19 omega   81.00  143.00   0.5000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      110.3999  -77.0000 -150.0000 124

 20 omega   39.00  108.00   0.5000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      110.3999  -94.0000   60.0000 138

 21 omega  -35.00   35.00   0.5000    0.5000
omega____ theta____ kappa____ phi______ frames
    -       37.5615  -29.0000  -18.0000 140

 22 omega -111.00   -6.00   0.5000    0.5000
omega____ theta____ kappa____ phi______ frames
    -      -37.5615  -37.0000   90.0000 210

 23 omega  -34.00   -7.00   0.5000    0.5000
omega____ theta____ kappa____ phi______ frames
    -      -37.5615  -37.0000 -150.0000 54

 24 omega -116.00  -43.00   0.5000    0.5000
omega____ theta____ kappa____ phi______ frames
    -      -37.5615  -37.0000 -150.0000 146

 25 omega   -6.00   19.00   0.5000    0.5000
omega____ theta____ kappa____ phi______ frames
    -       37.5615   99.0000   -9.8211 50

 26 omega    8.00   33.00   0.5000    0.5000
omega____ theta____ kappa____ phi______ frames
    -       44.0000   79.0000 -122.4482 50

 27 omega   11.00   36.00   0.5000    0.5000
omega____ theta____ kappa____ phi______ frames
    -       48.0000   83.0000 -160.9728 50

 28 omega   15.00   40.00   0.5000    0.5000
omega____ theta____ kappa____ phi______ frames
    -       52.0000   82.0000  103.9847 50

 29 omega   19.00   44.00   0.5000    0.5000
omega____ theta____ kappa____ phi______ frames
    -       56.0000   82.0000    7.3363 50

 30 omega   19.00   44.00   0.5000    0.5000
omega____ theta____ kappa____ phi______ frames
    -       56.0000   80.0000  -39.6015 50

 31 omega   20.00   45.00   0.5000    0.5000
omega____ theta____ kappa____ phi______ frames
    -       56.0000   82.0000  124.6415 50

 32 omega   19.00   44.00   0.5000    0.5000
omega____ theta____ kappa____ phi______ frames
    -       56.0000   80.0000  -79.0478 50

 33 omega  106.00  132.00   0.5000    0.5000
omega____ theta____ kappa____ phi______ frames
    -       64.0000   75.0000 -131.8461 52

 34 omega   28.00   60.00   0.5000    0.5000
omega____ theta____ kappa____ phi______ frames
    -       64.0000   75.0000 -131.8461 64

 35 omega   29.00   67.00   0.5000    0.5000
omega____ theta____ kappa____ phi______ frames
    -       64.0000   74.0000  169.6332 76

 36 omega   32.00   58.00   0.5000    0.5000
omega____ theta____ kappa____ phi______ frames
    -       64.0000   77.0000   15.9472 52

 37 omega   33.00   74.00   0.5000    0.5000
omega____ theta____ kappa____ phi______ frames
    -       68.0000   77.0000  -35.1868 82

 38 omega  113.00  139.00   0.5000    0.5000
omega____ theta____ kappa____ phi______ frames
    -       68.0000   76.0000   43.4916 52

 39 omega   32.00   69.00   0.5000    0.5000
omega____ theta____ kappa____ phi______ frames
    -       68.0000   76.0000   43.4916 74

 40 omega  107.00  133.00   0.5000    0.5000
omega____ theta____ kappa____ phi______ frames
    -       72.0000   77.0000   96.1352 52

 41 omega   36.00   73.00   0.5000    0.5000
omega____ theta____ kappa____ phi______ frames
    -       72.0000   77.0000  -94.5232 74

 42 omega   36.00   72.00   0.5000    0.5000
omega____ theta____ kappa____ phi______ frames
    -       72.0000   77.0000   96.1352 72

 43 omega   77.00  110.00   0.5000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      110.3999   61.0000 -180.0000 66

 44 omega   79.00  106.00   0.5000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      110.3999   61.0000    0.0000 54

 45 omega   74.00  100.00   0.5000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      110.3999   77.0000 -180.0000 52

 46 omega   78.00  110.00   0.5000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      110.3999   61.0000   60.0000 64

 47 omega   74.00  102.00   0.5000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      110.3999   77.0000  -90.0000 56

 48 omega   74.00  100.00   0.5000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      110.3999   77.0000 -120.0000 52

 49 omega   74.00  100.00   0.5000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      110.3999   77.0000 -150.0000 52

 50 omega   75.00  101.00   0.5000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      110.3999   77.0000  -60.0000 52

 51 omega   74.00  170.00   0.5000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      110.3999   77.0000   60.0000 192

 52 omega  116.00  142.00   0.5000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      110.3999   77.0000  120.0000 52

 53 omega   74.00  170.00   0.5000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      110.3999   77.0000   90.0000 192

 54 omega   77.00  104.00   0.5000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      110.3999   61.0000  -60.0000 54

 55 omega   74.00  101.00   0.5000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      110.3999   77.0000  120.0000 54

 56 omega   79.00  105.00   0.5000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      110.3999   61.0000 -150.0000 52

 57 omega   78.00  104.00   0.5000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      110.3999   61.0000  120.0000 52

 58 omega   77.00  151.00   0.5000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      110.3999   61.0000   30.0000 148

 59 omega   74.00  100.00   0.5000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      110.3999   77.0000   30.0000 52

 60 omega   74.00  103.00   0.5000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      110.3999   77.0000    0.0000 58

 61 omega  121.00  165.00   0.5000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      110.3999   77.0000  -30.0000 88

 62 omega   74.00  100.00   0.5000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      110.3999   77.0000  -30.0000 52

 63 omega   74.00  100.00   0.5000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      110.3999   77.0000  150.0000 52

 64 omega  122.00  147.00   0.5000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      110.3999   61.0000    0.0000 50

 65 omega   79.00  146.00   0.5000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      110.3999   61.0000  150.0000 134
;
_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      -0.0778074000
_diffrn_orient_matrix_UB_12      -0.1012608000
_diffrn_orient_matrix_UB_13      0.0232992000
_diffrn_orient_matrix_UB_21      -0.1315642000
_diffrn_orient_matrix_UB_22      0.0829607000
_diffrn_orient_matrix_UB_23      0.0432666000
_diffrn_orient_matrix_UB_31      0.0021552000
_diffrn_orient_matrix_UB_32      0.0145788000
_diffrn_orient_matrix_UB_33      -0.1167883000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0233
_diffrn_reflns_av_unetI/netI     0.0154
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            24488
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.778
_diffrn_reflns_theta_min         3.635
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.964
_exptl_absorpt_correction_T_max  0.789
_exptl_absorpt_correction_T_min  0.486
_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            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.407
_exptl_crystal_description       plate
_exptl_crystal_F_000             700
_exptl_crystal_size_max          0.441
_exptl_crystal_size_mid          0.2389
_exptl_crystal_size_min          0.1055
_refine_diff_density_max         0.835
_refine_diff_density_min         -1.018
_refine_diff_density_rms         0.068
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     402
_refine_ls_number_reflns         6301
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.0643
_refine_ls_R_factor_gt           0.0610
_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^)+(0.0980P)^2^+1.5035P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1750
_refine_ls_wR_factor_ref         0.1786
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5791
_reflns_number_total             6301
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6sc00614k2.cif
_cod_data_source_block           spa065b
_cod_depositor_comments
'Adding full bibliography for 1543067--1543076.cif.'
_cod_original_cell_volume        1589.31(16)
_cod_database_code               1543073
_chemical_oxdiff_formula         'C31 H35 B1 Cl2 F4 N2 O5'
_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:
 C2(H2A,H2B), C34(H34A,H34B), C3(H3A,H3B), C35(H35A,H35B), C12(H12A,H12B),
 C50(H50A,H50B)
2.b Aromatic/amide H refined with riding coordinates:
 C32(H32), C24(H24), C33(H33), C6(H6), C23(H23), C7(H7), C31(H31), C22(H22)
2.c Idealised Me refined as rotating group:
 C30(H30A,H30B,H30C), C27(H27A,H27B,H27C), C36(H36A,H36B,H36C), C13(H13A,H13B,
 H13C), C1(H1A,H1B,H1C)
;
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'