Zwitterionic [4]helicene: a water-soluble and reversible pH-triggered ECD/CPL chiroptical switch in the UV and red spectral regions.
Pascal, Simon; Besnard, Céline; Zinna, Francesco; Di Bari, Lorenzo; Le Guennic, Boris; Jacquemin, Denis; Lacour, Jérôme; Organic & biomolecular chemistry 14 (2016) 4590–4594; doi:10.1039/c6ob00752j

data_7155096
_publ_section_title
;
 Zwitterionic [4]helicene: a water-soluble and reversible pH-triggered
 ECD/CPL chiroptical switch in the UV and red spectral regions.
;
_journal_issue                   20
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              4590
_journal_page_last               4594
_journal_paper_doi               10.1039/c6ob00752j
_journal_volume                  14
_journal_year                    2016
_chemical_formula_moiety         'C2 F3 O2, H2 O, C28 H29 N2 O4'
_chemical_formula_sum            'C30 H31 F3 N2 O7'
_chemical_formula_weight         588.57
_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             2016-01-25
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2015.11.10 svn.r3248 for OlexSys, GUI svn.r5133)
;
_audit_update_record
;
2016-04-07 deposited with the CCDC.
2016-04-22 downloaded from the CCDC.
;
_cell_angle_alpha                111.624(3)
_cell_angle_beta                 97.490(3)
_cell_angle_gamma                110.940(4)
_cell_formula_units_Z            2
_cell_length_a                   10.9257(5)
_cell_length_b                   12.2016(4)
_cell_length_c                   12.7292(4)
_cell_measurement_reflns_used    11858
_cell_measurement_temperature    180(2)
_cell_measurement_theta_max      73.3440
_cell_measurement_theta_min      4.2970
_cell_volume                     1404.62(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    'SIR2004 (Burla et al., 2007)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      180(2)
_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 0.982
_diffrn_measurement_details
;
  1 omega   19.00   44.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000   80.0000    6.9143 25

  2 omega   29.00   70.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       64.0000   77.0000  -23.6683 41

  3 omega   88.00  114.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       64.0000   77.0000  -23.6683 26

  4 omega   74.00  105.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       60.0000   77.0000   26.4495 31

  5 omega  111.00  137.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       68.0000   77.0000   78.1796 26

  6 omega  113.00  156.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       72.0000   77.0000  123.1995 43

  7 omega  131.00  177.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      109.7499   77.0000   60.0000 46

  8 omega  105.00  177.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      109.7499   77.0000  -30.0000 72

  9 omega  117.00  143.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      109.7499   77.0000  -90.0000 26

 10 omega  111.00  178.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      109.7499   77.0000 -120.0000 67

 11 omega   81.00  112.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       64.0000   67.0000 -155.9199 31

 12 omega   78.00  103.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      109.7499   61.0000 -150.0000 25

 13 omega   78.00  107.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      109.7499   61.0000 -180.0000 29

 14 omega   74.00  166.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      109.7499   77.0000 -180.0000 92

 15 omega   78.00  103.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      109.7499   61.0000    0.0000 25

 16 omega   77.00  104.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      109.7499   61.0000  -30.0000 27

 17 omega   78.00  137.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      109.7499   61.0000  -60.0000 59

 18 omega   78.00  103.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      109.7499   61.0000   60.0000 25

 19 omega   79.00  127.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      109.7499   77.0000   60.0000 48

 20 omega  101.00  176.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      109.7499  111.0000   90.0000 75

 21 omega   79.00  131.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      109.7499   61.0000  150.0000 52

 22 omega   74.00  134.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      109.7499   77.0000   90.0000 60

 23 omega   74.00  100.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      109.7499   77.0000  -30.0000 26

 24 omega   74.00  177.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      109.7499   77.0000  -60.0000 103

 25 omega   78.00  138.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      109.7499   61.0000   30.0000 60

 26 omega   78.00  105.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      109.7499   61.0000  -90.0000 27

 27 omega   74.00  100.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      109.7499   77.0000 -120.0000 26

 28 omega   74.00  175.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      109.7499   77.0000 -150.0000 101

 29 omega   74.00  136.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      109.7499   77.0000    0.0000 62

 30 omega   74.00  175.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      109.7499   77.0000   30.0000 101

 31 omega   74.00   99.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      109.7499   77.0000  120.0000 25

 32 omega   74.00  158.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      109.7499   77.0000  150.0000 84

 33 omega   58.00  129.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       38.9365  178.0000  -90.0000 71

 34 omega   75.00  101.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      109.7499   77.0000  -90.0000 26

 35 omega   30.00   55.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       64.0000   67.0000 -155.9199 25

 36 omega   28.00   62.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       64.0000   77.0000 -136.1880 34

 37 omega   32.00   65.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       68.0000   76.0000  -84.8204 33

 38 omega   28.00   55.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       64.0000   77.0000  -56.3871 27

 39 omega   25.00   63.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       60.0000   77.0000   26.4495 38

 40 omega   32.00   59.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       68.0000   77.0000   78.1796 27

 41 omega   37.00   63.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       72.0000   76.0000  107.2548 26

 42 omega   39.00   83.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       72.0000   77.0000  123.1995 44

 43 omega   19.00   44.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000   82.0000   46.7750 25

 44 omega   -1.00   28.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       40.0000   90.0000   89.5810 29

 45 omega   19.00   44.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000   80.0000  143.1843 25

 46 omega  -39.00   -6.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -38.9365  -57.0000  150.0000 33

 47 omega  -69.00   34.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -38.9365   38.0000  120.0000 103

 48 omega  -70.00   39.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -38.9365   57.0000  -90.0000 109

 49 omega    4.00   29.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       44.0000   89.0000 -101.3351 25

 50 omega   19.00   44.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000   82.0000 -173.2796 25

 51 omega   35.00  107.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      109.7499  -94.0000   60.0000 72

 52 omega   88.00  125.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       38.9365 -178.0000   90.0000 37

 53 omega   28.00  116.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      109.7499 -111.0000   30.0000 88

 54 omega   24.00  105.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      109.7499  -94.0000  150.0000 81

 55 omega   25.00  106.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      109.7499  -94.0000 -120.0000 81

 56 omega -117.00   -7.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -38.9365  -57.0000  -30.0000 110

 57 omega -117.00  -42.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -38.9365  -57.0000  150.0000 75
;
_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      -0.0481911000
_diffrn_orient_matrix_UB_12      -0.0911438000
_diffrn_orient_matrix_UB_13      -0.1340214000
_diffrn_orient_matrix_UB_21      0.0608872000
_diffrn_orient_matrix_UB_22      0.1203769000
_diffrn_orient_matrix_UB_23      -0.0237808000
_diffrn_orient_matrix_UB_31      0.1380161000
_diffrn_orient_matrix_UB_32      -0.0086003000
_diffrn_orient_matrix_UB_33      0.0109880000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0349
_diffrn_reflns_av_unetI/netI     0.0230
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            21587
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        67.680
_diffrn_reflns_theta_max         73.395
_diffrn_reflns_theta_min         3.918
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.952
_exptl_absorpt_correction_T_max  0.892
_exptl_absorpt_correction_T_min  0.728
_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            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.392
_exptl_crystal_description       block
_exptl_crystal_F_000             616
_exptl_crystal_size_max          0.5829
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.1579
_refine_diff_density_max         0.278
_refine_diff_density_min         -0.358
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     420
_refine_ls_number_reflns         5561
_refine_ls_number_restraints     56
_refine_ls_restrained_S_all      1.132
_refine_ls_R_factor_all          0.0514
_refine_ls_R_factor_gt           0.0465
_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^)+(0.0726P)^2^+0.4140P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1259
_refine_ls_wR_factor_ref         0.1309
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4921
_reflns_number_total             5561
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6ob00752j2.cif
_cod_data_source_block           spa036
_cod_depositor_comments          'Adding full bibliography for 7155096.cif.'
_cod_original_cell_volume        1404.61(10)
_cod_database_code               7155096
_chemical_oxdiff_formula         'C30 H31 F2 N2 O7'
_reflns_odcompleteness_completeness 99.90
_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 O(H) groups, All O(H,H) groups
2. Restrained distances
 O5-H5
 0.84 with sigma of 0.02
 O35-H35A = O35-H35B
 0.85 with sigma of 0.02
 F41B-C39 \\sim F40A-C39 \\sim F42A-C39 \\sim F41A-C39 \\sim F40B-C39 \\sim
F42B-C39
 with sigma of 0.02
 F40A-F41A \\sim F41A-F42A \\sim F42A-F41A
 with sigma of 0.04
 F40B-F41B \\sim F41B-F42B \\sim F42B-F41B
 with sigma of 0.04
3. Rigid body (RIGU) restrains
 F41A, F40A, F42A, C39
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 F40B, F41B, F42B, C39
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4. Others
 Sof(F40B)=Sof(F41B)=Sof(F42B)=1-FVAR(1)
 Sof(F41A)=Sof(F40A)=Sof(F42A)=FVAR(1)
5.a Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C32(H32A,H32B), C11(H11A,H11B), C33(H33A,H33B)
5.b Aromatic/amide H refined with riding coordinates:
 C15(H15), C17(H17), C28(H28), C8(H8), C27(H27), C7(H7), C29(H29), C16(H16)
5.c Idealised Me refined as rotating group:
 C26(H26A,H26B,H26C), C13(H13A,H13B,H13C), C20(H20A,H20B,H20C), C34(H34A,H34B,
 H34C)
;
_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 2.221
_oxdiff_exptl_absorpt_empirical_full_min 0.464