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_1543074
_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, C28 H31 N2 O3'
_chemical_formula_sum            'C28 H31 B F4 N2 O3'
_chemical_formula_weight         530.36
_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
_audit_creation_date             2015-11-17
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2015.11.10 svn.r3248 for OlexSys, GUI svn.r5133)
;
_audit_update_record
;
2015-12-21 deposited with the CCDC.
2016-04-08 downloaded from the CCDC.
;
_cell_angle_alpha                69.935(5)
_cell_angle_beta                 78.524(5)
_cell_angle_gamma                82.802(5)
_cell_formula_units_Z            2
_cell_length_a                   7.8446(4)
_cell_length_b                   12.7594(7)
_cell_length_c                   13.7549(8)
_cell_measurement_reflns_used    6393
_cell_measurement_temperature    180.00(14)
_cell_measurement_theta_max      72.8560
_cell_measurement_theta_min      3.6690
_cell_volume                     1264.91(13)
_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    'SIR2004 (Burla et al., 2007)'
_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 0.999
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_details
;
  1 omega  -48.00   35.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -38.6865   38.0000  -30.0000 83

  2 omega   -3.00   22.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       40.0000   94.0000 -162.8849 25

  3 omega   19.00   44.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000   82.0000 -121.3376 25

  4 omega   29.00   61.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       64.0000   77.0000 -138.1744 32

  5 omega   81.00  141.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       64.0000   77.0000 -138.1744 60

  6 omega  100.00  178.00   1.0000    3.5850
omega____ theta____ kappa____ phi______ frames
    -      109.7499  111.0000  -60.0000 78

  7 omega  138.00  176.00   1.0000    3.5850
omega____ theta____ kappa____ phi______ frames
    -      109.7499   61.0000  -30.0000 38

  8 omega  111.00  142.00   1.0000    3.5850
omega____ theta____ kappa____ phi______ frames
    -      109.7499   77.0000   60.0000 31

  9 omega  131.00  158.00   1.0000    3.5850
omega____ theta____ kappa____ phi______ frames
    -      109.7499   61.0000  120.0000 27

 10 omega  120.00  148.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       64.0000   77.0000  109.6354 28

 11 omega  111.00  150.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       68.0000   76.0000  158.9393 39

 12 omega   77.00  103.00   1.0000    3.5850
omega____ theta____ kappa____ phi______ frames
    -      109.7499   61.0000   60.0000 26

 13 omega   80.00  111.00   1.0000    3.5850
omega____ theta____ kappa____ phi______ frames
    -      109.7499   61.0000   30.0000 31

 14 omega   77.00  135.00   1.0000    3.5850
omega____ theta____ kappa____ phi______ frames
    -      109.7499   61.0000   90.0000 58

 15 omega   75.00  113.00   1.0000    3.5850
omega____ theta____ kappa____ phi______ frames
    -      109.7499   77.0000  -30.0000 38

 16 omega  114.00  141.00   1.0000    3.5850
omega____ theta____ kappa____ phi______ frames
    -      109.7499   61.0000  -60.0000 27

 17 omega   74.00  100.00   1.0000    3.5850
omega____ theta____ kappa____ phi______ frames
    -      109.7499   77.0000   60.0000 26

 18 omega   74.00  176.00   1.0000    3.5850
omega____ theta____ kappa____ phi______ frames
    -      109.7499   77.0000   30.0000 102

 19 omega   78.00  176.00   1.0000    3.5850
omega____ theta____ kappa____ phi______ frames
    -      109.7499   61.0000 -120.0000 98

 20 omega   77.00  164.00   1.0000    3.5850
omega____ theta____ kappa____ phi______ frames
    -      109.7499   61.0000 -180.0000 87

 21 omega   78.00  146.00   1.0000    3.5850
omega____ theta____ kappa____ phi______ frames
    -      109.7499   61.0000 -150.0000 68

 22 omega   75.00  100.00   1.0000    3.5850
omega____ theta____ kappa____ phi______ frames
    -      109.7499   77.0000 -150.0000 25

 23 omega   74.00  101.00   1.0000    3.5850
omega____ theta____ kappa____ phi______ frames
    -      109.7499   77.0000 -180.0000 27

 24 omega   74.00  100.00   1.0000    3.5850
omega____ theta____ kappa____ phi______ frames
    -      109.7499   77.0000 -120.0000 26

 25 omega   74.00  177.00   1.0000    3.5850
omega____ theta____ kappa____ phi______ frames
    -      109.7499   77.0000  -90.0000 103

 26 omega   78.00  103.00   1.0000    3.5850
omega____ theta____ kappa____ phi______ frames
    -      109.7499   61.0000  -60.0000 25

 27 omega   77.00  103.00   1.0000    3.5850
omega____ theta____ kappa____ phi______ frames
    -      109.7499   61.0000  -30.0000 26

 28 omega   74.00  142.00   1.0000    3.5850
omega____ theta____ kappa____ phi______ frames
    -      109.7499   77.0000    0.0000 68

 29 omega   80.00  105.00   1.0000    3.5850
omega____ theta____ kappa____ phi______ frames
    -      109.7499   61.0000  120.0000 25

 30 omega   77.00  178.00   1.0000    3.5850
omega____ theta____ kappa____ phi______ frames
    -      109.7499   61.0000  150.0000 101

 31 omega   74.00  100.00   1.0000    3.5850
omega____ theta____ kappa____ phi______ frames
    -      109.7499   77.0000  150.0000 26

 32 omega   74.00  100.00   1.0000    3.5850
omega____ theta____ kappa____ phi______ frames
    -      109.7499   77.0000  120.0000 26

 33 omega   74.00  177.00   1.0000    3.5850
omega____ theta____ kappa____ phi______ frames
    -      109.7499   77.0000   90.0000 103

 34 omega   77.00  103.00   1.0000    3.5850
omega____ theta____ kappa____ phi______ frames
    -      109.7499   61.0000  -90.0000 26

 35 omega   33.00   69.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       68.0000   76.0000  -28.8714 36

 36 omega   28.00   62.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       64.0000   76.0000  -84.1310 34

 37 omega   24.00   76.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       60.0000   77.0000  -62.6866 52

 38 omega   32.00  135.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       68.0000   77.0000   32.0577 103

 39 omega   32.00   71.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       68.0000   76.0000  158.9393 39

 40 omega   28.00   66.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       64.0000   77.0000  109.6354 38

 41 omega   19.00   46.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000   81.0000   71.6555 27

 42 omega   15.00   40.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       52.0000   82.0000   28.6546 25

 43 omega   -3.00   22.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       40.0000   96.0000  -13.5316 25

 44 omega   19.00   44.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000   82.0000 -140.8388 25

 45 omega  -57.00   -6.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -38.6865  -57.0000    0.0000 51

 46 omega  -45.00   35.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -38.6865   38.0000  150.0000 80

 47 omega    9.00   34.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       48.0000   86.0000  152.1405 25

 48 omega   23.00  104.00   1.0000    3.5850
omega____ theta____ kappa____ phi______ frames
    -      109.7499  -94.0000  -60.0000 81

 49 omega   28.00  116.00   1.0000    3.5850
omega____ theta____ kappa____ phi______ frames
    -      109.7499 -111.0000   90.0000 88

 50 omega   48.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       38.6865 -142.0000  108.0000 56

 51 omega   30.00  109.00   1.0000    3.5850
omega____ theta____ kappa____ phi______ frames
    -      109.7499  -94.0000  120.0000 79

 52 omega   32.00   90.00   1.0000    3.5850
omega____ theta____ kappa____ phi______ frames
    -      109.7499  -94.0000    0.0000 58

 53 omega   24.00  104.00   1.0000    3.5850
omega____ theta____ kappa____ phi______ frames
    -      109.7499  -94.0000 -120.0000 80

 54 omega    2.00   83.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       38.6865  -99.0000 -150.0000 81

 55 omega -115.00   -6.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -38.6865  -57.0000 -180.0000 109

 56 omega -117.00  -60.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -38.6865  -57.0000    0.0000 57
;
_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      0.0728665000
_diffrn_orient_matrix_UB_12      -0.0956037000
_diffrn_orient_matrix_UB_13      0.0882408000
_diffrn_orient_matrix_UB_21      0.1167079000
_diffrn_orient_matrix_UB_22      -0.0457272000
_diffrn_orient_matrix_UB_23      -0.0824988000
_diffrn_orient_matrix_UB_31      0.1462240000
_diffrn_orient_matrix_UB_32      0.0731816000
_diffrn_orient_matrix_UB_33      -0.0059204000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0527
_diffrn_reflns_av_unetI/netI     0.0383
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            19658
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        67.680
_diffrn_reflns_theta_max         73.474
_diffrn_reflns_theta_min         3.470
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.922
_exptl_absorpt_correction_T_max  0.971
_exptl_absorpt_correction_T_min  0.758
_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    1.392
_exptl_crystal_description       plate
_exptl_crystal_F_000             556
_exptl_crystal_size_max          0.52
_exptl_crystal_size_mid          0.1471
_exptl_crystal_size_min          0.0328
_refine_diff_density_max         0.296
_refine_diff_density_min         -0.276
_refine_diff_density_rms         0.055
_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     348
_refine_ls_number_reflns         5013
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.0615
_refine_ls_R_factor_gt           0.0468
_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^)+(0.0835P)^2^+0.0515P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1223
_refine_ls_wR_factor_ref         0.1349
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3876
_reflns_number_total             5013
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6sc00614k2.cif
_cod_data_source_block           spa099
_cod_depositor_comments
'Adding full bibliography for 1543067--1543076.cif.'
_cod_original_cell_volume        1264.90(13)
_cod_database_code               1543074
_chemical_oxdiff_formula         'C28 H31 B1 F4 N2 O3'
_reflns_odcompleteness_completeness 99.91
_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:
 C26(H26A,H26B), C33(H33A,H33B), C27(H27A,H27B), C32(H32A,H32B)
2.b Aromatic/amide H refined with riding coordinates:
 C13(H13), C21(H21), C23(H23), C11(H11), C5(H5), C4(H4), C12(H12), C22(H22)
2.c Idealised Me refined as rotating group:
 C31(H31A,H31B,H31C), C34(H34A,H34B,H34C), C20(H20A,H20B,H20C), C1(H1A,H1B,
 H1C), C28(H28A,H28B,H28C)
;
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'