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_7157452
_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         'C25 H18 O3'
_chemical_formula_sum            'C25 H18 O3'
_chemical_formula_weight         366.39
_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_Hall           'P 2c -2ac'
_space_group_name_H-M_alt        'P c a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2019-11-12
_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                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   21.9993(4)
_cell_length_b                   12.5762(3)
_cell_length_c                   13.8028(3)
_cell_measurement_reflns_used    4370
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.7370
_cell_measurement_theta_min      5.1140
_cell_volume                     3818.79(14)
_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
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_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 0.999
_diffrn_measured_fraction_theta_max 0.999
_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    -10.00  36.00   0.50    2.50    --  -33.50  77.00   0.00   92
  2  \w    -84.00 -40.00   0.50    2.50    --  -33.50 -77.00-120.00   88
  3  \w    -61.00  -9.00   0.50    2.50    --  -33.50  77.00-120.00  104
  4  \w      6.00  31.00   0.50    2.50    --  -33.50  77.00-120.00   50
  5  \w    -72.00 -34.00   0.50    2.50    --  -33.50 178.00 -30.00   76
  6  \w    -30.00  -5.00   0.50    2.50    --  -33.50 -77.00-120.00   50
  7  \w     65.00  92.00   0.50    2.50    --   36.47  57.00 -30.00   54
  8  \w     20.00  60.00   0.50    2.50    --   36.47  57.00 -30.00   80
  9  \w     95.00 173.00   0.50   11.50    --  108.00  61.00   0.00  156
 10  \w    102.00 128.00   0.50   11.50    --  108.00 113.00 -46.00   52
 11  \w     79.00 109.00   0.50   11.50    --  108.00 -94.00 -90.00   60
 12  \w    153.00 178.00   0.50   11.50    --  108.00 113.00 -46.00   50
 13  \w    100.00 178.00   0.50   11.50    --  108.00 111.00  60.00  156
 14  \w    112.00 170.00   0.50   11.50    --  108.00  61.00-150.00  116
 15  \w     72.00 110.00   0.50   11.50    --  108.00 -45.00-120.00   76
 16  \w    -90.00 -65.00   0.50    2.00    --  -33.50 -57.00-150.00   50
 17  \w      8.00  44.00   0.50    2.00    --   36.47  77.00  60.00   72
 18  \w     72.00 110.00   0.50    2.00    --   36.47 178.00-120.00   76
 19  \w     68.00  96.00   0.50    2.00    --   36.47  77.00  60.00   56
 20  \w     43.00  69.00   0.50    2.00    --   36.47  57.00   0.00   52
 21  \w     75.00 101.00   0.50    2.00    --   36.47  57.00   0.00   52
 22  \w     37.00 105.00   0.50    6.00    --  108.00-111.00-120.00  136
 23  \w     40.00  66.00   0.50    6.00    --  108.00-111.00-150.00   52
 24  \w     46.00 121.00   0.50    6.00    --  108.00 -45.00  30.00  150
 25  \w     43.00  68.00   0.50    6.00    --  108.00 -94.00  60.00   50
;
_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      0.0044542000
_diffrn_orient_matrix_UB_12      0.0037853000
_diffrn_orient_matrix_UB_13      -0.1113486000
_diffrn_orient_matrix_UB_21      -0.0120995000
_diffrn_orient_matrix_UB_22      0.1206196000
_diffrn_orient_matrix_UB_23      0.0021626000
_diffrn_orient_matrix_UB_31      0.0688311000
_diffrn_orient_matrix_UB_32      0.0209466000
_diffrn_orient_matrix_UB_33      0.0075497000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0275
_diffrn_reflns_av_unetI/netI     0.0319
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            15382
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.076
_diffrn_reflns_theta_max         67.076
_diffrn_reflns_theta_min         4.019
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.664
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.45731
_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    1.275
_exptl_crystal_description       block
_exptl_crystal_F_000             1536
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.182
_refine_diff_density_min         -0.134
_refine_diff_density_rms         0.027
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.2(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     510
_refine_ls_number_reflns         6179
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.0521
_refine_ls_R_factor_gt           0.0422
_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^)+(0.0631P)^2^+0.1652P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1094
_refine_ls_wR_factor_ref         0.1193
_reflns_Friedel_coverage         0.911
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                5145
_reflns_number_total             6179
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0ob00479k2.cif
_cod_data_source_block           201911289
_cod_depositor_comments
'Adding full bibliography for 7157451--7157455.cif.'
_cod_original_cell_volume        3818.78(14)
_cod_database_code               7157452
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         C40H40O2N4
_shelx_estimated_absorpt_t_max   0.949
_shelx_estimated_absorpt_t_min   0.937
_reflns_odcompleteness_completeness 99.87
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.8(3)
 0.2(3)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3.a Aromatic/amide H refined with riding coordinates:
 C6(H6), C8(H8), C9(H9), C11(H11), C12(H12), C13(H13), C14(H14), C15(H15),
 C19(H19), C20(H20), C22(H22), C23(H23), C6'(H6'), C8'(H8'), C9'(H9'),
 C11'(H11'), C12'(H12'), C13'(H13'), C14'(H14'), C15'(H15'), C19'(H19'),
 C20'(H20'), C22'(H22'), C23'(H23')
3.b Idealised Me refined as rotating group:
 C24(H24A,H24B,H24C), C25(H25A,H25B,H25C), C24'(H24D,H24E,H24F), C25'(H25D,
 H25E,H25F)
;
_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 2.555
_oxdiff_exptl_absorpt_empirical_full_min 0.814