Diastereoselective photodimerization reactions of chromone-2-carboxamides to construct a C2-chiral scaffold.
Yagishita, Fumitoshi; Baba, Nozomi; Ueda, Yuki; Katabira, Satoshi; Kasashima, Yoshio; Mino, Takashi; Sakamoto, Masami; Organic & biomolecular chemistry 12 (2014) 9644–9649; doi:10.1039/c4ob01827c

data_7154126
_publ_section_title
;
 Diastereoselective photodimerization reactions of chromone-2-carboxamides
 to construct a C2-chiral scaffold.
;
_journal_issue                   47
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              9644
_journal_page_last               9649
_journal_paper_doi               10.1039/c4ob01827c
_journal_volume                  12
_journal_year                    2014
_chemical_absolute_configuration syn
_chemical_formula_sum            'C18 H15 N O3'
_chemical_formula_weight         293.31
_chemical_melting_point          396.5(5)
_chemical_name_systematic        (R)-N-(1-Phenylethyl)-2-chromonecarboxamide
_space_group_crystal_system      trigonal
_space_group_IT_number           145
_space_group_name_Hall           'P 32'
_space_group_name_H-M_alt        'P 32'
_symmetry_space_group_name_Hall  'P 32'
_symmetry_space_group_name_H-M   'P 32'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     'SHELXT(George Sheldrick, 2012)'
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_formula_units_Z            12
_cell_length_a                   13.4156(6)
_cell_length_b                   13.4156(6)
_cell_length_c                   28.8130(14)
_cell_measurement_reflns_used    9669
_cell_measurement_temperature    173
_cell_measurement_theta_max      66.7371
_cell_measurement_theta_min      3.8046
_cell_volume                     4491.0(4)
_computing_cell_refinement       'SAINT V8.32B (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.32B (Bruker AXS Inc., 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_diffrn_ambient_temperature      173
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEXII CCD area detector'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  'Bruker Helios multilayer confocal mirror'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0469
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            5285
_diffrn_reflns_theta_full        66.73
_diffrn_reflns_theta_max         66.73
_diffrn_reflns_theta_min         3.80
_diffrn_source                   'Bruker TXS fine-focus rotating anode'
_exptl_absorpt_coefficient_mu    0.725
_exptl_absorpt_correction_T_max  0.87
_exptl_absorpt_correction_T_min  0.78
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'SADABS V2012/1 (Bruker AXS Inc.)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.301
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             1848
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: CHCl3, Hexane'
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.239
_refine_diff_density_min         -0.306
_refine_ls_abs_structure_details
'No quotients, so Flack parameter determined by classical intensity fit'
_refine_ls_abs_structure_Flack   0.22(18)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     798
_refine_ls_number_reflns         5285
_refine_ls_number_restraints     229
_refine_ls_restrained_S_all      1.001
_refine_ls_R_factor_all          0.0438
_refine_ls_R_factor_gt           0.0438
_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^)+(0.1113P)^2^+0.1316P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1163
_refine_ls_wR_factor_ref         0.1164
_reflns_number_gt                5272
_reflns_number_total             5285
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c4ob01827c2.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '396-397' was changed to '396.5(5)' -
the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 2827 2014-09-09 07:05:25Z andrius 

 Adding full bibliography for 7154126--7154132.cif.
;
_cod_original_cell_volume        4491.0(5)
_cod_database_code               7154126
_shelx_res_checksum              43087
_shelx_hkl_checksum              16881