NHC-Catalyzed Reaction of Enals with Hydroxy Chalcones: Diastereoselective Synthesis of Functionalized Coumarins.
Bhunia, Anup; Patra, Atanu; Puranik, Vedavati G.; Biju, Akkattu T.; Organic letters 15 (2013) 1756–1759; doi:10.1021/ol400562z

data_1511920
_publ_section_title
;
 NHC-Catalyzed Reaction of Enals with Hydroxy Chalcones:
 Diastereoselective Synthesis of Functionalized Coumarins.
;
_journal_issue                   7
_journal_name_full               'Organic letters'
_journal_page_first              1756
_journal_page_last               1759
_journal_paper_doi               10.1021/ol400562z
_journal_volume                  15
_journal_year                    2013
_chemical_formula_moiety         'C24 H18 O2'
_chemical_formula_sum            'C24 H18 O2'
_chemical_formula_weight         338.38
_chemical_name_common            Coumarin
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 101.7470(8)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   12.9452(6)
_cell_length_b                   8.9427(4)
_cell_length_c                   31.393(2)
_cell_measurement_reflns_used    6964
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      24.44
_cell_measurement_theta_min      2.65
_cell_volume                     3558.1(3)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL PyMOL and PLATON'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0359
_diffrn_reflns_av_sigmaI/netI    0.0283
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            27804
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.86
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_T_max  0.9981
_exptl_absorpt_correction_T_min  0.9658
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker SADABS'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.263
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1424
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.151
_refine_diff_density_min         -0.233
_refine_diff_density_rms         0.037
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.141
_refine_ls_hydrogen_treatment    riding
_refine_ls_matrix_type           full
_refine_ls_number_parameters     469
_refine_ls_number_reflns         6270
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.141
_refine_ls_R_factor_all          0.0762
_refine_ls_R_factor_gt           0.0567
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0445P)^2^+1.1241P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1164
_refine_ls_wR_factor_ref         0.1245
_reflns_number_gt                4901
_reflns_number_total             6270
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol400562z_si_001.cif
_cod_data_source_block           C24H18O2compound3a
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_sg_symbol_H-M      'P21/c  '
_cod_database_code               1511920