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_7154131
_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 rm
_chemical_formula_sum            'C28 H26 N2 O10'
_chemical_formula_weight         550.51
_chemical_name_systematic
'Anti-HH photodimer of (S)-N-(1-methoxycarbonylethyl)-2-chromonecarboxamide'
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.021(3)
_cell_length_b                   15.273(5)
_cell_length_c                   21.484(7)
_cell_measurement_reflns_used    2736
_cell_measurement_temperature    173
_cell_measurement_theta_max      21.67
_cell_measurement_theta_min      2.32
_cell_volume                     2631.9(16)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      173
_diffrn_detector_area_resol_mean 8.333
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.986
_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  0.0502
_diffrn_reflns_av_sigmaI/netI    0.0644
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            14840
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         27.61
_diffrn_reflns_theta_min         1.64
_exptl_absorpt_coefficient_mu    0.107
_exptl_absorpt_correction_T_max  0.9894
_exptl_absorpt_correction_T_min  0.9687
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'SADABS Sheldrick 1996'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.389
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             1152
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: CHCl3/hexane'
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.646
_refine_diff_density_min         -0.350
_refine_diff_density_rms         0.064
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.3(12)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.896
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     365
_refine_ls_number_reflns         5909
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.896
_refine_ls_R_factor_all          0.0761
_refine_ls_R_factor_gt           0.0535
_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^)+(0.1000P)^2^+0.4661P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1372
_refine_ls_wR_factor_ref         0.1564
_reflns_number_gt                4432
_reflns_number_total             5909
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4ob01827c2.cif
_cod_data_source_block           saka426_p212121
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

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        2631.9(15)
_cod_original_sg_symbol_H-M      P2(1)2(1)2(1)
_cod_database_code               7154131