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_1543069
_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         'Cl, C27 H29 N2 O3'
_chemical_formula_sum            'C27 H29 Cl N2 O3'
_chemical_formula_weight         464.97
_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'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2015-12-18
_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                90
_cell_angle_beta                 90.901(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.9972(4)
_cell_length_b                   20.6791(7)
_cell_length_c                   13.5143(4)
_cell_measurement_reflns_used    5326
_cell_measurement_temperature    180.00(14)
_cell_measurement_theta_max      72.7060
_cell_measurement_theta_min      4.2250
_cell_volume                     2234.65(15)
_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    'ShelXT (Sheldrick, 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 1.000
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_details
;
  1 omega  144.00  172.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      109.7499   61.0000  -90.0000 28

  2 omega  111.00  178.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      109.7499  111.0000    0.0000 67

  3 omega   86.00  119.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -       38.9365  172.0000   53.0000 33

  4 omega   58.00  142.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      109.7499  178.0000   60.0000 84

  5 omega   89.00  140.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      109.7499   61.0000  -90.0000 51

  6 omega  100.00  175.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      109.7499   45.0000 -180.0000 75

  7 omega -110.00  -80.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      -38.9365  -99.0000    0.0000 30

  8 omega -124.00  -79.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      -38.9365  -99.0000  -60.0000 45

  9 omega -132.00  -58.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      -38.9365 -178.0000  -30.0000 74

 10 omega -124.00  -99.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      -38.9365  -99.0000    0.0000 25

 11 omega -112.00  -79.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      -38.9365  -99.0000   90.0000 33

 12 omega -124.00  -80.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      -38.9365  -99.0000  150.0000 44

 13 omega -109.00  -79.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      -38.9365  -99.0000 -120.0000 30

 14 omega -123.00  -82.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      -38.9365  -99.0000 -150.0000 41

 15 omega -124.00  -88.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      -38.9365  -99.0000   60.0000 36

 16 omega   60.00   98.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -       38.9365 -178.0000   90.0000 38

 17 omega   67.00  125.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -       38.9365 -178.0000  -60.0000 58

 18 omega   58.00   85.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -       38.9365  178.0000    0.0000 27

 19 omega   58.00   83.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -       38.9365  178.0000 -150.0000 25

 20 omega   45.00   74.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      109.7499  -61.0000  120.0000 29

 21 omega   79.00  131.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      109.7499  178.0000   30.0000 52

 22 omega   34.00  133.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      109.7499  -61.0000    0.0000 99

 23 omega  146.00  178.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      109.7499  111.0000  -60.0000 32

 24 omega  147.00  174.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      109.7499   30.0000   90.0000 27

 25 omega   85.00  144.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      109.7499   30.0000   90.0000 59

 26 omega   44.00  111.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      109.7499 -111.0000   30.0000 67

 27 omega   71.00  116.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      109.7499 -111.0000 -120.0000 45

 28 omega  100.00  145.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      109.7499  111.0000  120.0000 45

 29 omega   31.00   63.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      109.7499 -111.0000 -120.0000 32

 30 omega  102.00  142.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      109.7499  -61.0000  120.0000 40

 31 omega   58.00   83.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      109.7499  178.0000  -30.0000 25

 32 omega   72.00  109.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      109.7499  -94.0000   90.0000 37

 33 omega   79.00  116.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      109.7499   30.0000 -180.0000 37
;
_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      0.1401516000
_diffrn_orient_matrix_UB_12      -0.0500762000
_diffrn_orient_matrix_UB_13      -0.0144303000
_diffrn_orient_matrix_UB_21      -0.1154289000
_diffrn_orient_matrix_UB_22      -0.0535892000
_diffrn_orient_matrix_UB_23      0.0390952000
_diffrn_orient_matrix_UB_31      -0.0647068000
_diffrn_orient_matrix_UB_32      -0.0129451000
_diffrn_orient_matrix_UB_33      -0.1060947000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0509
_diffrn_reflns_av_unetI/netI     0.0436
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            16344
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        67.680
_diffrn_reflns_theta_max         73.599
_diffrn_reflns_theta_min         3.908
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.780
_exptl_absorpt_correction_T_max  0.956
_exptl_absorpt_correction_T_min  0.725
_exptl_absorpt_correction_type   analytical
_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)
Analytical numeric absorption correction using a multifaceted crystal
            model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
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    1.382
_exptl_crystal_description       needle
_exptl_crystal_F_000             984
_exptl_crystal_size_max          0.3429
_exptl_crystal_size_mid          0.0454
_exptl_crystal_size_min          0.0256
_refine_diff_density_max         0.428
_refine_diff_density_min         -0.410
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     305
_refine_ls_number_reflns         4437
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0733
_refine_ls_R_factor_gt           0.0545
_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^)+(0.0932P)^2^+0.5705P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1508
_refine_ls_wR_factor_ref         0.1636
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3331
_reflns_number_total             4437
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6sc00614k2.cif
_cod_data_source_block           simon_oh_b
_cod_depositor_comments
'Adding full bibliography for 1543067--1543076.cif.'
_cod_original_cell_volume        2234.66(15)
_cod_database_code               1543069
_chemical_oxdiff_formula         'C27 H29 Cl1 N2 O3'
_reflns_odcompleteness_completeness 99.98
_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, All C(H,H,H,H) groups
2. Restrained distances
 O24-H24
 0.82 with sigma of 0.02
3.a Secondary CH2 refined with riding coordinates:
 C30(H30A,H30B), C27(H27A,H27B), C31(H31A,H31B), C28(H28A,H28B)
3.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C17(H17), C4(H4), C25(H25), C16(H16), C15(H15), C26(H26), C3(H3)
3.c Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C32(H32A,H32B,H32C), C8(H8A,H8B,H8C), C29(H29A,H29B,H29C)
;
_shelx_shelxl_version_number     2014/7
_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 2.896
_oxdiff_exptl_absorpt_empirical_full_min 0.413