A visible-light-induced "on-off" one-pot synthesis of 3-arylacetylene coumarins with AIE properties.
Wu, Xinjie; Jia, Ming; Huang, Mengmeng; Kim, Jung Keun; Zhao, Zheng; Liu, Junkai; Xi, Jinhu; Li, Yabo; Wu, Yangjie; Organic & biomolecular chemistry 18 (2020) 3346–3353; doi:10.1039/d0ob00479k

data_7157455
_publ_section_title
;
 A visible-light-induced &quot;on-off&quot; one-pot synthesis of
 3-arylacetylene coumarins with AIE properties.
;
_journal_issue                   17
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              3346
_journal_page_last               3353
_journal_paper_doi               10.1039/d0ob00479k
_journal_volume                  18
_journal_year                    2020
_chemical_formula_moiety         'C23 H14 O2'
_chemical_formula_sum            'C23 H14 O2'
_chemical_formula_weight         322.34
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2019-11-08
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-11-20 deposited with the CCDC.	2020-04-06 downloaded from the CCDC.
;
_cell_angle_alpha                87.690(5)
_cell_angle_beta                 77.763(5)
_cell_angle_gamma                71.943(6)
_cell_formula_units_Z            4
_cell_length_a                   10.9195(8)
_cell_length_b                   11.7513(7)
_cell_length_c                   14.2060(6)
_cell_measurement_reflns_used    3391
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.5420
_cell_measurement_theta_min      3.9470
_cell_volume                     1693.10(19)
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2312
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_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   -102.00 -15.00   1.00    1.00    --  -33.50 -57.00  30.00   87
  2  \w   -105.00  38.00   1.00    1.00    --  -33.50   0.00  90.00  143
  3  \w   -108.00 -32.00   1.00    1.00    --  -33.50 178.00 -90.00   76
  4  \w    -52.00 -18.00   1.00    1.00    --  -33.50   0.00  90.00   34
  5  \w     35.00  72.00   1.00    1.00    --   36.47 -99.00 -60.00   37
  6  \w     11.00  72.00   1.00    1.00    --   36.47 -99.00  90.00   61
  7  \w     -4.00  73.00   1.00    1.00    --   36.47 -99.00-150.00   77
  8  \w     26.00  62.00   1.00    1.00    --   36.47 -77.00  90.00   36
  9  \w     71.00  96.00   1.00    1.00    --   36.47 178.00   0.00   25
 10  \w    -27.00  19.00   1.00    1.00    --   36.47 -77.00  90.00   46
 11  \w    -31.00  46.00   1.00    1.00    --   36.47 -37.00 120.00   77
 12  \w     64.00 108.00   1.00    1.00    --   36.47 178.00  90.00   44
 13  \w     86.00 136.00   1.00    7.00    --  108.00  30.00   0.00   50
 14  \w     39.00 132.00   1.00    7.00    --  108.00 -77.00  60.00   93
 15  \w     38.00 125.00   1.00    7.00    --  108.00 -30.00   0.00   87
 16  \w    100.00 178.00   1.00    7.00    --  108.00  30.00  90.00   78
 17  \w     39.00 127.00   1.00    7.00    --  108.00 -45.00 -90.00   88
 18  \w     37.00  85.00   1.00    7.00    --  108.00 -30.00 120.00   48
 19  \w     54.00 100.00   1.00    7.00    --  108.00 -94.00 -30.00   46
 20  \w     38.00 116.00   1.00    7.00    --  108.00 -45.00-180.00   78
 21  \w     94.00 120.00   1.00    7.00    --  108.00  45.00 -90.00   26
 22  \w     60.00  93.00   1.00    7.00    --  108.00 -94.00 -90.00   33
 23  \w     84.00 111.00   1.00    7.00    --  108.00-111.00-180.00   27
 24  \w    114.00 177.00   1.00    7.00    --  108.00  15.00-150.00   63
 25  \w     40.00  66.00   1.00    7.00    --  108.00-111.00-180.00   26
 26  \w     58.00 110.00   1.00    7.00    --  108.00 -94.00  30.00   52
 27  \w     64.00  95.00   1.00    7.00    --  108.00  15.00-150.00   31
 28  \w     37.00 112.00   1.00    7.00    --  108.00-111.00-120.00   75
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0784980000
_diffrn_orient_matrix_UB_12      -0.1280965000
_diffrn_orient_matrix_UB_13      0.0219370000
_diffrn_orient_matrix_UB_21      0.1280679000
_diffrn_orient_matrix_UB_22      0.0344724000
_diffrn_orient_matrix_UB_23      -0.0230228000
_diffrn_orient_matrix_UB_31      -0.0217286000
_diffrn_orient_matrix_UB_32      0.0378166000
_diffrn_orient_matrix_UB_33      0.1063547000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0230
_diffrn_reflns_av_unetI/netI     0.0328
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            11792
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        67.079
_diffrn_reflns_theta_max         67.079
_diffrn_reflns_theta_min         3.958
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.634
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.86954
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
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    1.265
_exptl_crystal_description       block
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.204
_refine_diff_density_min         -0.164
_refine_diff_density_rms         0.032
_refine_ls_extinction_coef       0.0019(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     452
_refine_ls_number_reflns         5950
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.018
_refine_ls_R_factor_all          0.0637
_refine_ls_R_factor_gt           0.0473
_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^)+(0.0717P)^2^+0.1125P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1252
_refine_ls_wR_factor_ref         0.1428
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4481
_reflns_number_total             5950
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0ob00479k2.cif
_cod_data_source_block           201911284
_cod_depositor_comments
'Adding full bibliography for 7157451--7157455.cif.'
_cod_original_cell_volume        1693.11(19)
_cod_database_code               7157455
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         C40H40O2N4
_shelx_estimated_absorpt_t_max   0.939
_shelx_estimated_absorpt_t_min   0.905
_reflns_odcompleteness_completeness 98.80
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C8(H8), C9(H9), C11(H11), C12(H12), C13(H13), C14(H14),
 C15(H15), C19(H19), C20(H20), C21(H21), C22(H22), C23(H23), C6'(H6'), C7'(H7'),
  C8'(H8'), C9'(H9'), C11'(H11'), C12'(H12'), C13'(H13'), C14'(H14'),
 C15'(H15'), C19'(H19'), C20'(H20'), C21'(H21'), C22'(H22'), C23'(H23')
;
_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 1.448
_oxdiff_exptl_absorpt_empirical_full_min 0.872