Chirality-activated mechanoluminescence from aggregation-induced emission enantiomers with high contrast mechanochromism and force-induced delayed fluorescence
Chen, Yitong; Xu, Chao; Xu, Bingjia; Mao, Zhu; Li, Jian-An; Yang, Zhan; Peethani, Naga Raju; Liu, Cong; Shi, Guang; Gu, Feng Long; Zhang, Yi; Chi, Zhenguo; Materials Chemistry Frontiers 3 (2019) 1800–; doi:10.1039/C9QM00312F

data_1554678
_publ_section_title
;
 Chirality-activated mechanoluminescence from aggregation-induced emission
 enantiomers with high contrast mechanochromism and force-induced delayed
 fluorescence
;
_journal_issue                   9
_journal_name_full               'Materials Chemistry Frontiers'
_journal_page_first              1800
_journal_paper_doi               10.1039/C9QM00312F
_journal_volume                  3
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C30 H22 N2 O2 S'
_chemical_formula_sum            'C30 H22 N2 O2 S'
_chemical_formula_weight         474.55
_chemical_name_systematic        (S)-ImNT
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2018-06-11
_audit_creation_method
;
Olex2 1.2
(compiled 2016.09.09 svn.r3337 for OlexSys, GUI svn.r5227)
;
_audit_update_record
;
2019-03-27 deposited with the CCDC.	2019-06-20 downloaded from the CCDC.
;
_cell_angle_alpha                85.7850(10)
_cell_angle_beta                 78.3710(10)
_cell_angle_gamma                89.3450(10)
_cell_formula_units_Z            4
_cell_length_a                   12.1350(2)
_cell_length_b                   12.8327(2)
_cell_length_c                   15.1864(2)
_cell_measurement_reflns_used    32281
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      73.7430
_cell_measurement_theta_min      3.6940
_cell_volume                     2310.08(6)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_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      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2913
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.982
_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     12.00  37.00   1.00    1.87    --   48.00  84.00 105.81   25
  2  \w     34.00  60.00   1.00    1.87    --   68.00  77.00 129.85   26
  3  \w     38.00  64.00   1.00    1.87    --   68.00  77.00  89.88   26
  4  \w     81.00 107.00   1.00    1.87    --   56.00  76.00  58.68   26
  5  \w    108.00 134.00   1.00    1.87    --   72.00  77.00 166.10   26
  6  \w    128.00 154.00   1.00    7.00    --  108.22  77.00  90.00   26
  7  \w    108.00 136.00   1.00    7.00    --  108.22  61.00 120.00   28
  8  \w     79.00 119.00   1.00    7.00    --  108.22  61.00  30.00   40
  9  \w     78.00 104.00   1.00    7.00    --  108.22  61.00  90.00   26
 10  \w     79.00 107.00   1.00    7.00    --  108.22  61.00 120.00   28
 11  \w     75.00 178.00   1.00    7.00    --  108.22  77.00 150.00  103
 12  \w     79.00 170.00   1.00    7.00    --  108.22  61.00   0.00   91
 13  \w    118.00 175.00   1.00    7.00    --  108.22  61.00 -60.00   57
 14  \w    115.00 177.00   1.00    7.00    --  108.22  77.00-120.00   62
 15  \w    110.00 136.00   1.00    1.87    --   68.00  76.00 -70.63   26
 16  \w    114.00 178.00   1.00    7.00    --  108.22  77.00-150.00   64
 17  \w     79.00 106.00   1.00    7.00    --  108.22  61.00-120.00   27
 18  \w     75.00 101.00   1.00    7.00    --  108.22  77.00-150.00   26
 19  \w     75.00 153.00   1.00    7.00    --  108.22  77.00-180.00   78
 20  \w     78.00 103.00   1.00    7.00    --  108.22  61.00 -30.00   25
 21  \w     75.00 101.00   1.00    7.00    --  108.22  77.00   0.00   26
 22  \w     75.00 160.00   1.00    7.00    --  108.22  77.00  30.00   85
 23  \w     79.00 106.00   1.00    7.00    --  108.22  61.00 -60.00   27
 24  \w     75.00 146.00   1.00    7.00    --  108.22  77.00 -30.00   71
 25  \w     75.00 167.00   1.00    7.00    --  108.22  77.00  60.00   92
 26  \w     78.00 104.00   1.00    7.00    --  108.22  61.00 150.00   26
 27  \w     76.00 103.00   1.00    7.00    --  108.22  77.00  90.00   27
 28  \w     75.00 172.00   1.00    7.00    --  108.22  77.00 120.00   97
 29  \w     75.00 147.00   1.00    7.00    --  108.22  77.00 -90.00   72
 30  \w     75.00 112.00   1.00    7.00    --  108.22  77.00-120.00   37
 31  \w     39.00  78.00   1.00    1.87    --   72.00  75.00 -47.10   39
 32  \w     31.00 142.00   1.00    1.87    --   64.00  76.00  -3.05  111
 33  \w     38.00  74.00   1.00    1.87    --   72.00  77.00 166.10   36
 34  \w     35.00  61.00   1.00    1.87    --   68.00  76.00  74.74   26
 35  \w     23.00  67.00   1.00    1.87    --   56.00  76.00  58.68   44
 36  \w     17.00  42.00   1.00    1.87    --   52.00  82.00 164.97   25
 37  \w     -8.00  17.00   1.00    1.87    --   36.00 102.00 157.65   25
 38  \w      7.00  32.00   1.00    1.87    --   44.00  87.00  39.73   25
 39  \w     17.00  42.00   1.00    1.87    --   52.00  82.00 -44.37   25
 40  \w     35.00  62.00   1.00    1.87    --   68.00  76.00 -70.63   27
 41  \w     34.00  61.00   1.00    1.87    --   68.00  77.00-110.81   27
 42  \w     35.00  63.00   1.00    1.87    --   68.00  76.00-154.06   28
 43  \w     17.00  42.00   1.00    1.87    --   52.00  82.00-146.70   25
 44  \w     17.00  42.00   1.00    1.87    --   52.00  82.00 -94.26   25
 45  \w     -9.00  16.00   1.00    1.87    --   36.00 104.00 -65.41   25
 46  \w    -69.00  34.00   1.00    1.87    --  -40.84  77.00  60.00  103
 47  \w    -63.00 -23.00   1.00    1.87    --  -40.84 -37.00  30.00   40
 48  \w    -92.00 -15.00   1.00    1.87    --  -40.84 -37.00 150.00   77
 49  \w   -106.00 -69.00   1.00    1.87    --  -40.84 -37.00  30.00   37
 50  \w   -115.00 -11.00   1.00    1.87    --  -40.84 -57.00 -60.00  104
 51  \w     29.00  88.00   1.00    1.87    --   40.84-125.00-180.00   59
 52  \w     45.00 122.00   1.00    7.00    --  108.22-125.00-180.00   77
 53  \w     76.00 105.00   1.00    7.00    --  108.22 -94.00-120.00   29
 54  \w     33.00 103.00   1.00    7.00    --  108.22 -94.00 -30.00   70
 55  \w     34.00 101.00   1.00    7.00    --  108.22 -94.00  60.00   67
 56  \w     39.00 137.00   1.00    7.00    --  108.22 -61.00 150.00   98
 57  \w    -72.00  38.00   1.00    1.87    --  -40.84  77.00 -60.00  110
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0756128000
_diffrn_orient_matrix_UB_12      0.0965585000
_diffrn_orient_matrix_UB_13      0.0177464000
_diffrn_orient_matrix_UB_21      0.0124486000
_diffrn_orient_matrix_UB_22      0.0250374000
_diffrn_orient_matrix_UB_23      -0.1023129000
_diffrn_orient_matrix_UB_31      -0.1045339000
_diffrn_orient_matrix_UB_32      -0.0673799000
_diffrn_orient_matrix_UB_33      0.0008979000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0275
_diffrn_reflns_av_unetI/netI     0.0314
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            37878
_diffrn_reflns_point_group_measured_fraction_full 0.954
_diffrn_reflns_point_group_measured_fraction_max 0.925
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.832
_diffrn_reflns_theta_min         3.453
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.495
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.22262
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.364
_exptl_crystal_description       block
_exptl_crystal_F_000             992
_exptl_crystal_preparation       Luminescent
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.198
_refine_diff_density_min         -0.187
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details
;
 Flack x determined using 7833 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.001(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1261
_refine_ls_number_reflns         17289
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0293
_refine_ls_R_factor_gt           0.0290
_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^)+(0.0525P)^2^+0.2128P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0783
_refine_ls_wR_factor_ref         0.0789
_reflns_Friedel_coverage         0.884
_reflns_Friedel_fraction_full    0.910
_reflns_Friedel_fraction_max     0.868
_reflns_number_gt                17091
_reflns_number_total             17289
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9qm00312f4.cif
_cod_data_source_block           (S)-ImNT
_cod_database_code               1554678
_chemical_oxdiff_formula         'C H O N S'
_chemical_oxdiff_usercomment     S-IMNT
_reflns_odcompleteness_completeness 99.94
_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
2.a Ternary CH refined with riding coordinates:
 C01G(H01G), C020(H020), C021(H021), C033(H033)
2.b Secondary CH2 refined with riding coordinates:
 C02Q(H02L,H02M), C02W(H02A,H02B), C038(H03V,H03W), C03B(H1AA,H), C03F(H03A,
 H03B), C03J(H3AA,HA), C03K(H03C,H03D), C03N(H03L,H03N), C03Q(H0AA,HB),
 C03S(H03O,H03P), C03V(H03F,H03H), C03W(H03Q,H03S)
2.c Aromatic/amide H refined with riding coordinates:
 C00S(H00S), C00T(H00T), C019(H019), C01A(H01A), C01D(H01D), C01E(H01E),
 C01H(H01H), C01I(H01I), C01M(H01M), C01N(H01N), C01Q(H01Q), C01W(H01W),
 C01Y(H01Y), C01Z(H01Z), C022(H022), C023(H023), C024(H024), C025(H025),
 C026(H026), C029(H029), C02C(H02C), C02D(H02D), C02E(H02E), C02F(H02F),
 C02G(H02G), C02H(H02H), C02I(H02I), C02J(H02J), C02K(H02K), C02O(H02O),
 C02P(H02P), C02R(H02R), C02S(H02S), C02T(H02T), C02U(H02U), C02V(H02V),
 C02X(H02X), C02Y(H02Y), C02Z(H02Z), C031(H031), C032(H032), C034(H034),
 C035(H035), C036(H036), C037(H037), C039(H039), C03A(H03I), C03C(H03J),
 C03D(H03X), C03E(H03E), C03G(H03G), C03H(H2AA), C03I(H03K), C03L(H03Y),
 C03M(H03M), C03O(H03Z), C03P(H03), C03R(H03R), C03T(H03T), C03U(H03U)
;
_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 3.065
_oxdiff_exptl_absorpt_empirical_full_min 0.528