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_7157453
_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         'C24 H13 F3 O2'
_chemical_formula_sum            'C24 H13 F3 O2'
_chemical_formula_weight         390.34
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2019-11-07
_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                 110.026(8)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.8769(8)
_cell_length_b                   11.8650(6)
_cell_length_c                   14.2912(11)
_cell_measurement_reflns_used    1789
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      69.6380
_cell_measurement_theta_min      3.9470
_cell_volume                     1892.1(2)
_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 0.999
_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    -85.00  -5.00   1.00    2.50    --  -33.50 -77.00 -30.00   80
  2  \w    -41.00 -15.00   1.00    2.50    --  -33.50 -57.00-180.00   26
  3  \w    -88.00 -43.00   1.00    2.50    --  -33.50 -57.00 120.00   45
  4  \w    -93.00 -60.00   1.00    2.50    --  -33.50 -57.00-180.00   33
  5  \w     62.00  87.00   1.00    2.50    --   36.47 178.00-120.00   25
  6  \w     77.00 102.00   1.00    2.50    --   36.47 178.00 -60.00   25
  7  \w     58.00 109.00   1.00    2.50    --   36.47 178.00-180.00   51
  8  \w     58.00 102.00   1.00    2.50    --   36.47 178.00  90.00   44
  9  \w    -27.00  46.00   1.00    2.50    --   36.47 -57.00-120.00   73
 10  \w     88.00 172.00   1.00   10.00    --  108.00  45.00 150.00   84
 11  \w    112.00 141.00   1.00   10.00    --  108.00  77.00-120.00   29
 12  \w     43.00  70.00   1.00   10.00    --  108.00 -77.00   0.00   27
 13  \w     42.00 120.00   1.00   10.00    --  108.00 -45.00   0.00   78
 14  \w     84.00 134.00   1.00   10.00    --  108.00 -30.00 120.00   50
 15  \w     37.00  63.00   1.00   10.00    --  108.00 -30.00 120.00   26
 16  \w     50.00 109.00   1.00   10.00    --  108.00 -94.00-180.00   59
 17  \w     71.00 109.00   1.00   10.00    --  108.00 -77.00   0.00   38
 18  \w     43.00  96.00   1.00   10.00    --  108.00 -94.00 -30.00   53
 19  \w    110.00 143.00   1.00   10.00    --  108.00 178.00  30.00   33
 20  \w     60.00  98.00   1.00   10.00    --  108.00 178.00  30.00   38
;
_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      -0.1280686000
_diffrn_orient_matrix_UB_12      0.0430326000
_diffrn_orient_matrix_UB_13      -0.0175468000
_diffrn_orient_matrix_UB_21      0.0011211000
_diffrn_orient_matrix_UB_22      0.0633881000
_diffrn_orient_matrix_UB_23      -0.0937611000
_diffrn_orient_matrix_UB_31      -0.0514381000
_diffrn_orient_matrix_UB_32      -0.1048471000
_diffrn_orient_matrix_UB_33      -0.0637929000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0234
_diffrn_reflns_av_unetI/netI     0.0304
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            7164
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.063
_diffrn_reflns_theta_max         67.063
_diffrn_reflns_theta_min         3.962
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.902
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.76891
_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    1.370
_exptl_crystal_description       block
_exptl_crystal_F_000             800
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.327
_refine_diff_density_min         -0.441
_refine_diff_density_rms         0.042
_refine_ls_extinction_coef       0.0013(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   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     273
_refine_ls_number_reflns         3371
_refine_ls_number_restraints     67
_refine_ls_restrained_S_all      1.133
_refine_ls_R_factor_all          0.0800
_refine_ls_R_factor_gt           0.0605
_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^)+(0.0872P)^2^+0.6254P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1653
_refine_ls_wR_factor_ref         0.1862
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2485
_reflns_number_total             3371
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0ob00479k2.cif
_cod_data_source_block           201911285
_cod_depositor_comments
'Adding full bibliography for 7157451--7157455.cif.'
_cod_original_cell_volume        1892.2(2)
_cod_database_code               7157453
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         C40H40O2N4F3
_shelx_estimated_absorpt_t_max   0.915
_shelx_estimated_absorpt_t_min   0.899
_reflns_odcompleteness_completeness 99.86
_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. Restrained distances
 F3A-C24
 1.35 with sigma of 0.02
 F3-F1 \\sim F3-F2 \\sim F1-F2 \\sim F1A-F2A \\sim F1A-F3A \\sim F2A-F3A
 with sigma of 0.04
 C24-F3 \\sim C24-F1 \\sim C24-F2 \\sim C24-F1A \\sim C24-F2A \\sim C24-F3A
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(F3) \\sim Ueq, Uanis(F1A) \\sim Ueq, Uanis(F2) \\sim Ueq, Uanis(F2A)
\\sim Ueq, Uanis(F1) \\sim Ueq, Uanis(F3A) \\sim Ueq: with sigma of 0.01 and
sigma for terminal atoms of 0.02
Uanis(F1) = Uanis(F1A)
Uanis(F2) = Uanis(F2A)
Uanis(F3) = Uanis(F3A)
4. Others
 Sof(F1A)=Sof(F2A)=Sof(F3A)=1-FVAR(1)
 Sof(F1)=Sof(F2)=Sof(F3)=FVAR(1)
5.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), 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 1.395
_oxdiff_exptl_absorpt_empirical_full_min 0.827