Total Facial Discrimination of 1,3-Dipolar Cycloadditions in a d-Erythrose 1,3-Dioxane Template: Computational Studies of a Concerted Mechanism.
Sousa, Cristina E. A.; Ribeiro, António M P; Gil Fortes, António; Cerqueira, Nuno M. F. S. A.; Alves, Maria J.; The Journal of organic chemistry 82 (2017) 982–991; doi:10.1021/acs.joc.6b02518

data_4032308
_publ_section_title
;
 Total Facial Discrimination of 1,3-Dipolar Cycloadditions in a
 d-Erythrose 1,3-Dioxane Template: Computational Studies of a Concerted
 Mechanism.
;
_journal_issue                   2
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              982
_journal_page_last               991
_journal_paper_doi               10.1021/acs.joc.6b02518
_journal_volume                  82
_journal_year                    2017
_chemical_absolute_configuration rm
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C20 H19 N3 O4'
_chemical_formula_sum            'C20 H19 N3 O4'
_chemical_formula_weight         365.38
_chemical_name_common            cs35pt
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      4
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2011-01-17T13:07:31-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 105.330(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   5.6268(11)
_cell_length_b                   17.614(3)
_cell_length_c                   9.1708(17)
_cell_measurement_reflns_used    3075
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.37
_cell_measurement_theta_min      2.31
_cell_measurement_wavelength     0.71073
_cell_volume                     876.6(3)
_computing_cell_refinement       'APEX2 v2010.11-3 (Bruker AXS, 2010)'
_computing_data_collection       'APEX2 v2010.11-3 (Bruker AXS, 2010)'
_computing_data_reduction        'APEX2 v2010.11-3 (Bruker AXS, 2010)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR97 (Altomare et al., 1999)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker X8 kappa APEXII CCD'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0262
_diffrn_reflns_av_unetI/netI     0.0264
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            8149
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         2.3
_exptl_absorpt_coefficient_mu    0.098
_exptl_absorpt_correction_T_max  0.9785
_exptl_absorpt_correction_T_min  0.8620
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'BRUKER AXS - SADABS'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.384
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             384
_exptl_crystal_size_max          0.62
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.23
_refine_diff_density_min         -0.19
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         2070
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.039
_refine_ls_R_factor_gt           0.0324
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0375P)^2^+0.1880P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0749
_refine_ls_wR_factor_ref         0.0785
_reflns_number_gt                1869
_reflns_number_total             2070
_reflns_threshold_expression     >2\s(I)
_cod_data_source_file            jo6b02518_si_003.cif
_cod_data_source_block           um01hma1n
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4032308