Aggregate-state-dependent photochromism and circularly polarized luminescence of a chiral biquinoline amphiphile.
Zhao, Chenyang; Li, Zujian; Ji, Lukang; Wang, Hanxiao; Ouyang, Guanghui; Liu, Minghua; Chemical communications (Cambridge, England) 60 (2024) 6047–6050; doi:10.1039/d4cc01810a

data_7133068
_publ_section_title
;
 Aggregate-state-dependent photochromism and circularly polarized
 luminescence of a chiral biquinoline amphiphile.
;
_journal_issue                   47
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              6047
_journal_page_last               6050
_journal_paper_doi               10.1039/d4cc01810a
_journal_volume                  60
_journal_year                    2024
_chemical_absolute_configuration rm
_chemical_formula_moiety         'C30 H24 N4 O10, 1[C2H6SO]'
_chemical_formula_sum            'C36 H44 N4 O13 S3'
_chemical_formula_weight         836.93
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2022-07-14
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2024-04-17 deposited with the CCDC.	2024-05-15 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 101.092(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   17.0638(3)
_cell_length_b                   4.99240(10)
_cell_length_c                   23.7104(4)
_cell_measurement_reflns_used    23684
_cell_measurement_temperature    169.99(14)
_cell_measurement_theta_max      76.8120
_cell_measurement_theta_min      2.6180
_cell_volume                     1982.14(6)
_computing_cell_refinement       'CrysAlisPro 1.171.41.121a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.121a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.121a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      169.99(14)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -88.00  -3.00   0.50    0.11    --  -47.70 111.00 131.00  170
  2  \w      9.00  88.00   0.50    0.11    --   47.70-111.00  37.00  158
  3  \w   -108.00 -32.00   0.50    1.30    -- -104.50 111.00 131.00  152
  4  \w   -174.00 -82.00   0.50    1.30    -- -104.50-111.00  37.00  184
  5  \w     35.00 108.00   0.50    1.30    --  107.36-111.00  37.00  146
  6  \w     88.00 178.00   0.50    1.30    --  107.36 111.00 131.00  180
  7  \w   -120.00 -74.00   0.50    0.11    --  -47.70-125.00-120.00   92
  8  \w   -120.00 -74.00   0.50    0.11    --  -47.70-125.00  90.00   92
  9  \w   -120.00 -33.00   0.50    0.11    --  -47.70 -57.00 -30.00  174
 10  \w   -120.00 -74.00   0.50    0.11    --  -47.70-125.00-150.00   92
 11  \w   -120.00 -74.00   0.50    0.11    --  -47.70-125.00 150.00   92
 12  \w    -23.00  28.00   0.50    0.11    --  -47.70  19.00 120.00  102
 13  \w    -27.00  30.00   0.50    0.11    --   47.70 -19.00  60.00  114
 14  \w    -25.00  47.00   0.50    0.11    --   47.70 -38.00 120.00  144
 15  \w    -62.00 -32.00   0.50    1.30    -- -104.50  57.00 150.00   60
 16  \w   -174.00 -92.00   0.50    1.30    -- -104.50 -46.00 -45.35  164
 17  \w    -62.00 -32.00   0.50    1.30    -- -104.50  57.00   0.00   60
 18  \w    -62.00 -32.00   0.50    1.30    -- -104.50  57.00 120.00   60
 19  \w    -62.00 -32.00   0.50    1.30    -- -104.50  57.00 -60.00   60
 20  \w    -62.00 -32.00   0.50    1.30    -- -104.50  57.00  90.00   60
 21  \w   -174.00 -90.00   0.50    1.30    -- -104.50 -48.00  63.16  168
 22  \w   -174.00 -84.00   0.50    1.30    -- -104.50 -71.00  49.03  180
 23  \w     94.00 178.00   0.50    1.30    --  107.36  38.00 -60.00  168
 24  \w     35.00 106.00   0.50    1.30    --  107.36 -99.00 150.00  142
 25  \w     80.00 178.00   0.50    1.30    --  107.36 125.00  60.00  196
 26  \w     35.00  69.00   0.50    1.30    --  107.36 -57.00  60.00   68
 27  \w     35.00 106.00   0.50    1.30    --  107.36 -99.00-150.00  142
 28  \w     35.00  69.00   0.50    1.30    --  107.36 -57.00  30.00   68
 29  \w     35.00 111.00   0.50    1.30    --  107.36-125.00 -30.00  152
 30  \w     93.00 178.00   0.50    1.30    --  107.36  57.00 -90.00  170
 31  \w     35.00 106.00   0.50    1.30    --  107.36 -99.00  60.00  142
 32  \w     35.00 106.00   0.50    1.30    --  107.36 -99.00  30.00  142
 33  \w     35.00 111.00   0.50    1.30    --  107.36-125.00  60.00  152
 34  \w     35.00 106.00   0.50    1.30    --  107.36 -99.00-120.00  142
 35  \w     35.00  69.00   0.50    1.30    --  107.36 -57.00  90.00   68
 36  \w     35.00 111.00   0.50    1.30    --  107.36-125.00-150.00  152
 37  \w     35.00  69.00   0.50    1.30    --  107.36 -57.00-150.00   68
 38  \w     25.00 120.00   0.50    0.11    --   47.70  77.00-150.00  190
 39  \w     25.00 120.00   0.50    0.11    --   47.70  77.00  60.00  190
 40  \w     25.00 120.00   0.50    0.11    --   47.70  77.00 -60.00  190
 41  \w     25.00 120.00   0.50    0.11    --   47.70  77.00-180.00  190
 42  \w     25.00 120.00   0.50    0.11    --   47.70  77.00 120.00  190
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0014285000
_diffrn_orient_matrix_UB_12      0.0291743000
_diffrn_orient_matrix_UB_13      -0.0648878000
_diffrn_orient_matrix_UB_21      0.0184231000
_diffrn_orient_matrix_UB_22      0.3010769000
_diffrn_orient_matrix_UB_23      0.0083699000
_diffrn_orient_matrix_UB_31      0.0901053000
_diffrn_orient_matrix_UB_32      -0.0610558000
_diffrn_orient_matrix_UB_33      0.0102962000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0864
_diffrn_reflns_av_unetI/netI     0.0418
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            37145
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.951
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.410
_diffrn_reflns_theta_min         1.899
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'PhotonJet R (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.302
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.40096
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.121a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.402
_exptl_crystal_description       cube
_exptl_crystal_F_000             880
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.438
_refine_diff_density_min         -0.793
_refine_diff_density_rms         0.070
_refine_ls_abs_structure_details
;
 Flack x determined using 2836 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.051(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     591
_refine_ls_number_reflns         8038
_refine_ls_number_restraints     44
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.0792
_refine_ls_R_factor_gt           0.0740
_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^)+(0.1036P)^2^+1.5011P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1921
_refine_ls_wR_factor_ref         0.1962
_reflns_Friedel_coverage         0.742
_reflns_Friedel_fraction_full    0.990
_reflns_Friedel_fraction_max     0.919
_reflns_number_gt                7404
_reflns_number_total             8038
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4cc01810a2.cif
_cod_data_source_block           tx10887_auto
_cod_depositor_comments          'Adding full bibliography for 7133068.cif.'
_cod_database_code               7133068
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         CHONS
_chemical_oxdiff_usercomment     C,H,S
_shelx_estimated_absorpt_t_max   0.977
_shelx_estimated_absorpt_t_min   0.656
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Restrained distances
 S3A-C36A
 1.76 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
C36A \\sim S3A \\sim O13A \\sim C37A: within 1.9A with sigma of 0.01 and sigma
for terminal atoms of 0.02 within 1.9A
S2A \\sim C34A \\sim C35A \\sim O12A: within 1.9A with sigma of 0.01 and sigma
for terminal atoms of 0.02 within 1.9A
Uanis(C35A) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
4. Others
 Sof(S2A)=Sof(O12A)=Sof(C34A)=Sof(H34D)=Sof(H34E)=Sof(H34F)=Sof(C35A)=
 Sof(H35D)=Sof(H35E)=Sof(H35F)=1-FVAR(1)
 Sof(S2)=Sof(C34)=Sof(H34A)=Sof(H34B)=Sof(H34C)=Sof(O12)=Sof(C33)=Sof(H33A)=
 Sof(H33B)=Sof(H33C)=FVAR(1)
 Sof(S3A)=Sof(O13A)=Sof(C37A)=Sof(H37A)=Sof(H37B)=Sof(H37C)=Sof(C36A)=
 Sof(H36D)=Sof(H36E)=Sof(H36F)=1-FVAR(2)
 Sof(S3)=Sof(C35)=Sof(H35A)=Sof(H35B)=Sof(H35C)=Sof(C36)=Sof(H36A)=Sof(H36B)=
 Sof(H36C)=Sof(O13)=FVAR(2)
5.a Riding coordinates:
 O8(H8), O3(H3)
5.b Ternary CH refined with riding coordinates:
 C26(H26), C11(H11)
5.c Secondary CH2 refined with riding coordinates:
 C29(H29A,H29B), C13(H13A,H13B), C28(H28A,H28B), C14(H14A,H14B)
5.d Aromatic/amide H refined with riding coordinates:
 N4(H4), N2(H2), C17(H17), C21(H21), C20(H20), C2(H2A), C23(H23), C22(H22),
 C5(H5A), C8(H8A), C6(H6), C7(H7)
5.e Idealised Me refined as rotating group:
 C35(H35A,H35B,H35C), C32(H32A,H32B,H32C), C34(H34A,H34B,H34C), C31(H31A,H31B,
 H31C), C36(H36A,H36B,H36C), C33(H33A,H33B,H33C), C34A(H34D,H34E,H34F),
 C35A(H35D,H35E,H35F), C37A(H37A,H37B,H37C), C36A(H36D,H36E,H36F)
5.f Idealised tetrahedral OH refined as rotating group:
 O10(H10), O5(H5)
;
_shelx_res_checksum              86168
_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 1.995
_oxdiff_exptl_absorpt_empirical_full_min 0.438