Preparation of 3-Acyl-4-arylcoumarins via Metal-Free Tandem Oxidative Acylation/Cyclization between Alkynoates with Aldehydes.
Mi, Xia; Wang, Chenyang; Huang, Mengmeng; Wu, Yusheng; Wu, Yangjie; The Journal of organic chemistry 80 (2014) 148–; doi:10.1021/jo502220b

data_4030374
_publ_section_title
;
 Preparation of 3-Acyl-4-arylcoumarins via Metal-Free Tandem Oxidative
 Acylation/Cyclization between Alkynoates with Aldehydes.
;
_journal_issue                   1
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              148
_journal_paper_doi               10.1021/jo502220b
_journal_volume                  80
_journal_year                    2014
_chemical_formula_moiety         'C23 H16 O3'
_chemical_formula_sum            'C23 H16 O3'
_chemical_formula_weight         340.36
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2014-09-04
_audit_creation_method
;
Olex2 1.2
(compiled 2014.08.28 svn.r2986 for OlexSys, GUI svn.r4874)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   11.9905(2)
_cell_length_b                   8.82516(14)
_cell_length_c                   34.0165(6)
_cell_measurement_reflns_used    3687
_cell_measurement_temperature    291(2)
_cell_measurement_theta_max      72.1770
_cell_measurement_theta_min      4.5060
_cell_volume                     3599.56(10)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      291.15
_diffrn_detector_area_resol_mean 16.2312
_diffrn_measured_fraction_theta_full 0.978
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_details
;
  1 omega  -58.00  -32.00   0.5000    0.5000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  132.0000   66.0000 52

  2 omega  -58.00  -33.00   0.5000    0.5000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  136.0000 -116.0000 50

  3 omega   46.00   71.00   0.5000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000 -132.0000   -2.0000 50

  4 omega   73.00   98.00   0.5000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000 -136.0000  179.0000 50

  5 omega   60.00  122.00   0.5000   11.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000 -132.0000   -2.0000 124

  6 omega   60.00   85.00   0.5000   11.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000 -136.0000  179.0000 50

  7 omega   92.00  117.00   0.5000   11.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  132.0000   66.0000 50

  8 omega   25.00   65.00   0.5000    0.5000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   77.0000 -180.0000 80

  9 omega  -22.00   19.00   0.5000    0.5000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   77.0000 -180.0000 82

 10 omega   61.00  121.00   0.5000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000   57.0000 -180.0000 120

 11 omega  -11.00   85.00   0.5000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000  -77.0000  -60.0000 192

 12 omega   32.00   57.00   0.5000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000   37.0000   90.0000 50

 13 omega   98.00  126.00   0.5000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000   37.0000   90.0000 56

 14 omega   62.00   89.00   0.5000   11.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -30.0000  120.0000 54

 15 omega  122.00  166.00   0.5000   11.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   45.0000   60.0000 88

 16 omega   44.00   97.00   0.5000   11.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -45.0000 -180.0000 106

 17 omega   55.00   87.00   0.5000   11.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -30.0000 -150.0000 64

 18 omega  103.00  134.00   0.5000   11.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   61.0000 -150.0000 62

 19 omega   45.00  108.00   0.5000   11.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -94.0000 -180.0000 126
;
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0675096000
_diffrn_orient_matrix_UB_12      0.0025388000
_diffrn_orient_matrix_UB_13      0.0385294000
_diffrn_orient_matrix_UB_21      -0.1090563000
_diffrn_orient_matrix_UB_22      -0.0105173000
_diffrn_orient_matrix_UB_23      0.0237929000
_diffrn_orient_matrix_UB_31      0.0075377000
_diffrn_orient_matrix_UB_32      -0.1742328000
_diffrn_orient_matrix_UB_33      -0.0008664000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0268
_diffrn_reflns_av_unetI/netI     0.0238
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       41
_diffrn_reflns_limit_l_min       -40
_diffrn_reflns_number            10253
_diffrn_reflns_theta_full        72.37
_diffrn_reflns_theta_max         72.37
_diffrn_reflns_theta_min         4.51
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.665
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.93527
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour
;
;
_exptl_crystal_density_diffrn    1.256
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description
;
;
_exptl_crystal_F_000             1424
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.186
_refine_diff_density_min         -0.189
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         3486
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.085
_refine_ls_R_factor_all          0.0614
_refine_ls_R_factor_gt           0.0524
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0738P)^2^+0.8142P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1514
_refine_ls_wR_factor_ref         0.1597
_reflns_number_gt                2875
_reflns_number_total             3486
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo502220b_si_002.cif
_cod_data_source_block           201408160
_cod_depositor_comments          'Adding full bibliography for 4030374.cif.'
_cod_original_cell_volume        3599.55(10)
_cod_database_code               4030374
_chemical_oxdiff_formula         C20H20N1O4
_reflns_odcompleteness_completeness 99.84
_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:
 C1(H1), C2(H2), C3(H3), C4(H4), C11(H11), C12(H12), C13(H13), C14(H14),
 C15(H15), C18(H18), C19(H19), C21(H21), C22(H22)
2.b Idealised Me refined as rotating group:
 C23(H23A,H23B,H23C)
;
_olex2_submission_special_instructions 'No special instructions were received'