An efficient light on-off one-pot method for the synthesis of 3-styryl coumarins from aryl alkynoates.
Kong, Hongjun; Li, Qingrui; Yin, Yunnian; Huang, Mengmeng; Kim, Jung Keun; Zhu, Yu; Li, Yabo; Wu, Yangjie; Organic & biomolecular chemistry 17 (2019) 4621–4628; doi:10.1039/c9ob00421a

data_7156789
_publ_section_title
;
 An efficient light on-off one-pot method for the synthesis of 3-styryl
 coumarins from aryl alkynoates.
;
_journal_issue                   18
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              4621
_journal_page_last               4628
_journal_paper_doi               10.1039/c9ob00421a
_journal_volume                  17
_journal_year                    2019
_chemical_formula_moiety         'C27 H18 O2'
_chemical_formula_sum            'C27 H18 O2'
_chemical_formula_weight         374.41
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2018-08-22
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2018-08-23 deposited with the CCDC.    2019-04-16 downloaded from the CCDC.
;
_cell_angle_alpha                78.293(6)
_cell_angle_beta                 85.937(5)
_cell_angle_gamma                65.446(6)
_cell_formula_units_Z            2
_cell_length_a                   9.4150(6)
_cell_length_b                   10.3881(7)
_cell_length_c                   11.1903(7)
_cell_measurement_reflns_used    1239
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      64.1670
_cell_measurement_theta_min      4.7570
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_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_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)
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_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
  1 omega  -49.00   37.00   0.5000    1.0000
omega____ theta____ kappa____ phi______ frames
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  2 omega -102.00  -15.00   0.5000    1.0000
omega____ theta____ kappa____ phi______ frames
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  3 omega   14.00  107.00   0.5000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   37.0000  -60.0000 186

  4 omega   -4.00   77.00   0.5000    1.0000
omega____ theta____ kappa____ phi______ frames
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  5 omega   -4.00   77.00   0.5000    1.0000
omega____ theta____ kappa____ phi______ frames
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  6 omega   18.00  105.00   0.5000    1.0000
omega____ theta____ kappa____ phi______ frames
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  7 omega    8.00  106.00   0.5000    1.0000
omega____ theta____ kappa____ phi______ frames
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  8 omega  -33.00   65.00   0.5000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -77.0000 -180.0000 196

  9 omega   20.00   46.00   0.5000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   37.0000  150.0000 52

 10 omega   57.00   93.00   0.5000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000 -120.0000 72

 11 omega   10.00   36.00   0.5000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -99.0000 -180.0000 52

 12 omega   20.00   66.00   0.5000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -99.0000  -30.0000 92

 13 omega   60.00  109.00   0.5000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000 -180.0000 98

 14 omega   42.00   98.00   0.5000    3.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  -90.0000 112

 15 omega  144.00  170.00   0.5000    3.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000 -150.0000 52

 16 omega   37.00   85.00   0.5000    3.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  120.0000 96

 17 omega   37.00   68.00   0.5000    3.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000    0.0000 62

 18 omega   69.00  128.00   0.5000    3.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -61.0000 -180.0000 118

 19 omega   37.00  115.00   0.5000    3.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000  150.0000 156

 20 omega   45.00   83.00   0.5000    3.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000   90.0000 76

 21 omega  102.00  128.00   0.5000    3.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000 -150.0000 52

 22 omega   78.00  104.00   0.5000    3.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000   90.0000 52

 23 omega   82.00  115.00   0.5000    3.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000 -120.0000 66

 24 omega  125.00  153.00   0.5000    3.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -15.0000 -120.0000 56

 25 omega   67.00  117.00   0.5000    3.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -61.0000  120.0000 100

 26 omega   59.00   85.00   0.5000    3.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  -60.0000 52

 27 omega  141.00  178.00   0.5000    3.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000  -60.0000 74

 28 omega   42.00   87.00   0.5000    3.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000   30.0000 90

 29 omega   83.00  135.00   0.5000    3.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000  -60.0000 104

 30 omega   68.00  104.00   0.5000    3.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000  -60.0000 72

 31 omega   43.00  122.00   0.5000    3.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -15.0000 -120.0000 158

 32 omega   37.00   66.00   0.5000    3.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000 -180.0000 58

 33 omega   88.00  130.00   0.5000    3.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -77.0000  -60.0000 84
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.1543770000
_diffrn_orient_matrix_UB_12      0.1361133000
_diffrn_orient_matrix_UB_13      -0.0216485000
_diffrn_orient_matrix_UB_21      -0.0889986000
_diffrn_orient_matrix_UB_22      -0.0880724000
_diffrn_orient_matrix_UB_23      0.0672038000
_diffrn_orient_matrix_UB_31      0.0248501000
_diffrn_orient_matrix_UB_32      0.0361815000
_diffrn_orient_matrix_UB_33      0.1215986000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0265
_diffrn_reflns_av_unetI/netI     0.0409
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            6939
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.075
_diffrn_reflns_theta_max         67.075
_diffrn_reflns_theta_min         4.035
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.625
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.96923
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
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    1.276
_exptl_crystal_description       needle
_exptl_crystal_F_000             392
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.131
_refine_diff_density_min         -0.167
_refine_diff_density_rms         0.034
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     262
_refine_ls_number_reflns         3476
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.018
_refine_ls_R_factor_all          0.0927
_refine_ls_R_factor_gt           0.0531
_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^)+(0.0754P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1390
_refine_ls_wR_factor_ref         0.1704
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2039
_reflns_number_total             3476
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9ob00421a2.cif
_cod_data_source_block           201808345
_cod_depositor_comments
'Adding full bibliography for 7156785--7156790.cif.'
_cod_original_cell_volume        974.65(12)
_cod_database_code               7156789
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         C15H15O3N2
_shelx_estimated_absorpt_t_max   0.969
_shelx_estimated_absorpt_t_min   0.835
_reflns_odcompleteness_completeness 99.83
_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:
 C3(H3), C4(H4), C6(H6), C7(H7), C8(H8), C9(H9), C10(H10), C13(H13), C14(H14),
 C15(H15), C16(H16), C17(H17), C20(H20), C21(H21), C24(H24), C25(H25), C26(H26),
  C27(H27)
;
_olex2_submission_special_instructions 'No special instructions were received'