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_7157454
_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 H15 F O3'
_chemical_formula_sum            'C24 H15 F O3'
_chemical_formula_weight         370.36
_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             2019-11-15
_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                   21.9897(6)
_cell_length_b                   12.2777(3)
_cell_length_c                   13.5508(4)
_cell_measurement_reflns_used    3453
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      69.4180
_cell_measurement_theta_min      4.0300
_cell_volume                     3658.48(17)
_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 0.998
_diffrn_measured_fraction_theta_max 0.998
_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    -97.00 -49.00   1.00    1.50    --  -33.50 178.00-120.00   48
  2  \w   -101.00 -51.00   1.00    1.50    --  -33.50 -57.00 -90.00   50
  3  \w    -45.00 -17.00   1.00    1.50    --  -33.50 -57.00-150.00   28
  4  \w     71.00 110.00   1.00    1.50    --   36.47 178.00-150.00   39
  5  \w     41.00  68.00   1.00    1.50    --   36.47 -99.00 -90.00   27
  6  \w     60.00 109.00   1.00    1.50    --   36.47 178.00 -30.00   49
  7  \w     -4.00  22.00   1.00    1.50    --   36.47 -99.00 -90.00   26
  8  \w     59.00 106.00   1.00    5.00    --  108.00-111.00 -60.00   47
  9  \w    105.00 178.00   1.00    5.00    --  108.00 111.00-150.00   73
 10  \w     40.00  78.00   1.00    5.00    --  108.00 -94.00-180.00   38
 11  \w    100.00 178.00   1.00    5.00    --  108.00 111.00  90.00   78
 12  \w     47.00 131.00   1.00    5.00    --  108.00 -30.00 120.00   84
 13  \w   -102.00 -76.00   1.00    2.50    --  -33.50 178.00-180.00   26
 14  \w     47.00  72.00   1.00    2.50    --   36.47 -19.00  90.00   25
 15  \w     31.00  62.00   1.00    2.50    --   36.47 -99.00  60.00   31
 16  \w    -32.00  33.00   1.00    2.50    --   36.47 -19.00  90.00   65
 17  \w     45.00  88.00   1.00    2.50    --   36.47  56.00-117.00   43
 18  \w     32.00  58.00   1.00    2.50    --   36.47 -99.00 -30.00   26
 19  \w     59.00 105.00   1.00    3.00    --  108.00 -94.00 -30.00   46
 20  \w    111.00 148.00   1.00    3.00    --  108.00  61.00   0.00   37
 21  \w    125.00 151.00   1.00    3.00    --  108.00  61.00  60.00   26
 22  \w     92.00 104.00   1.00    3.00    --  108.00  61.00 -60.00   12
;
_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      -0.0024437000
_diffrn_orient_matrix_UB_12      0.0829850000
_diffrn_orient_matrix_UB_13      0.0850143000
_diffrn_orient_matrix_UB_21      0.0690592000
_diffrn_orient_matrix_UB_22      -0.0120387000
_diffrn_orient_matrix_UB_23      0.0146894000
_diffrn_orient_matrix_UB_31      0.0110280000
_diffrn_orient_matrix_UB_32      0.0932896000
_diffrn_orient_matrix_UB_33      -0.0737560000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0319
_diffrn_reflns_av_unetI/netI     0.0371
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            13127
_diffrn_reflns_point_group_measured_fraction_full 0.750
_diffrn_reflns_point_group_measured_fraction_max 0.750
_diffrn_reflns_theta_full        67.337
_diffrn_reflns_theta_max         67.337
_diffrn_reflns_theta_min         3.600
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.782
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.90866
_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    1.345
_exptl_crystal_description       block
_exptl_crystal_F_000             1536
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.163
_refine_diff_density_min         -0.150
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details
;
 Flack x determined using 876 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.15(18)
_refine_ls_extinction_coef       0.00211(16)
_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   1.021
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     508
_refine_ls_number_reflns         4929
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.021
_refine_ls_R_factor_all          0.0573
_refine_ls_R_factor_gt           0.0421
_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^)+(0.0545P)^2^+0.0553P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1018
_refine_ls_wR_factor_ref         0.1161
_reflns_Friedel_coverage         0.435
_reflns_Friedel_fraction_full    0.477
_reflns_Friedel_fraction_max     0.477
_reflns_number_gt                3789
_reflns_number_total             4929
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0ob00479k2.cif
_cod_data_source_block           201911292
_cod_depositor_comments
'Adding full bibliography for 7157451--7157455.cif.'
_cod_original_cell_volume        3658.47(17)
_cod_database_code               7157454
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         C40H40O2N4F1
_shelx_estimated_absorpt_t_max   0.926
_shelx_estimated_absorpt_t_min   0.885
_reflns_odcompleteness_completeness 99.95
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.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')
2.b Idealised Me refined as rotating group:
 C24(H24A,H24B,H24C), C24'(H24D,H24E,H24F)
;
_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 1.297
_oxdiff_exptl_absorpt_empirical_full_min 0.932