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_7156788
_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         'C24 H17 Cl O2'
_chemical_formula_sum            'C24 H17 Cl O2'
_chemical_formula_weight         372.82
_space_group_crystal_system      orthorhombic
_space_group_IT_number           62
_space_group_name_Hall           '-P 2ac 2n'
_space_group_name_H-M_alt        'P n m a'
_symmetry_space_group_name_Hall  '-P 2ac 2n'
_symmetry_space_group_name_H-M   'P n m a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2018-09-17
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2018-10-08 deposited with the CCDC.    2019-04-16 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.6928(4)
_cell_length_b                   7.0340(3)
_cell_length_c                   21.7643(8)
_cell_measurement_reflns_used    1090
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.1460
_cell_measurement_theta_min      4.0160
_cell_volume                     1943.14(13)
_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    'olex2.solve (Bourhis et al., 2015)'
_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 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details
;
  1 omega  -49.00   33.00   0.5000    3.2500
omega____ theta____ kappa____ phi______ frames
    -      -33.5000   37.0000   60.0000 164

  2 omega  -49.00  -22.00   0.5000    3.2500
omega____ theta____ kappa____ phi______ frames
    -      -33.5000   37.0000  -90.0000 54

  3 omega   -1.00   36.00   0.5000    3.2500
omega____ theta____ kappa____ phi______ frames
    -      -33.5000   37.0000  -90.0000 74

  4 omega   57.00   82.00   0.5000    3.2500
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000   30.0000 50

  5 omega   60.00   88.00   0.5000    3.2500
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000  -90.0000 56

  6 omega   76.00  106.00   0.5000    3.2500
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000 -150.0000 60

  7 omega   39.00  104.00   0.5000   33.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000  150.0000 130

  8 omega   54.00  107.00   0.5000   33.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000  -90.0000 106

  9 omega   54.00   80.00   0.5000   33.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  -90.0000 52

 10 omega   37.00   62.00   0.5000   33.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000   30.0000 50

 11 omega   38.00  169.00   0.5000   33.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000    0.0000 -120.0000 262
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.1064366000
_diffrn_orient_matrix_UB_12      -0.0495235000
_diffrn_orient_matrix_UB_13      -0.0300128000
_diffrn_orient_matrix_UB_21      -0.0386947000
_diffrn_orient_matrix_UB_22      0.0846571000
_diffrn_orient_matrix_UB_23      -0.0612662000
_diffrn_orient_matrix_UB_31      0.0436408000
_diffrn_orient_matrix_UB_32      0.1958040000
_diffrn_orient_matrix_UB_33      0.0189016000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0278
_diffrn_reflns_av_unetI/netI     0.0246
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            4210
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.077
_diffrn_reflns_theta_max         67.076
_diffrn_reflns_theta_min         4.032
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.856
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.86935
_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    1.274
_exptl_crystal_description       prism
_exptl_crystal_F_000             776
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.295
_refine_diff_density_min         -0.319
_refine_diff_density_rms         0.099
_refine_ls_extinction_coef       0.0013(5)
_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   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     159
_refine_ls_number_reflns         1890
_refine_ls_number_restraints     42
_refine_ls_restrained_S_all      1.214
_refine_ls_R_factor_all          0.0932
_refine_ls_R_factor_gt           0.0728
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1336P)^2^+0.3204P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2076
_refine_ls_wR_factor_ref         0.2326
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1302
_reflns_number_total             1890
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9ob00421a2.cif
_cod_data_source_block           201809371
_cod_depositor_comments
'Adding full bibliography for 7156785--7156790.cif.'
_cod_original_cell_volume        1943.16(13)
_cod_database_code               7156788
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         C15H15O3N4Cl1
_shelx_estimated_absorpt_t_max   0.836
_shelx_estimated_absorpt_t_min   0.644
_reflns_odcompleteness_completeness 99.66
_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. Restrained distances
 C6-C5
 1.4 with sigma of 0.02
 C6-C1
 1.4 with sigma of 0.02
 C5-C4
 1.4 with sigma of 0.02
 C4-C3
 1.5 with sigma of 0.02
 C2-C1
 1.4 with sigma of 0.02
 C3-C2
 1.6 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C5) \\sim Ueq, Uanis(C4) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
Uanis(C5) \\sim Ueq, Uanis(C4) \\sim Ueq, Uanis(C3) \\sim Ueq, Uanis(C2) \\sim
Ueq, Uanis(C1) \\sim Ueq, Uanis(C6) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
4. Others
 Fixed Sof: H18A(0.5) H18B(0.5) H18C(0.5)
5.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C7(H7), C8(H8), C14(H14), C16(H16),
 C17(H17), C20(H20), C21(H21)
5.b Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C)
;
_olex2_submission_special_instructions 'No special instructions were received'