Stereoselective Synthesis of Pyrido- and Pyrrolo[1,2- c][1,3]oxazin-1-ones via a Nucleophilic Addition-Cyclization Process of N, O-Acetal with Ynamides.
Han, Pan; Mao, Zhuo-Ya; Si, Chang-Mei; Zhou, Zhu; Wei, Bang-Guo; Lin, Guo-Qiang; The Journal of organic chemistry 84 (2019) 914–923; doi:10.1021/acs.joc.8b02795

data_4036011
_publ_section_title
;
 Stereoselective Synthesis of Pyrido- and Pyrrolo[1,2-
 c][1,3]oxazin-1-ones via a Nucleophilic Addition-Cyclization Process of
 N, O-Acetal with Ynamides.
;
_journal_issue                   2
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              914
_journal_page_last               923
_journal_paper_doi               10.1021/acs.joc.8b02795
_journal_volume                  84
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_formula_sum            'C28 H28 N2 O5 S'
_chemical_formula_weight         504.58
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 100.710(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.7480(8)
_cell_length_b                   25.918(2)
_cell_length_c                   10.3862(7)
_cell_measurement_reflns_used    9981
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      53.342
_cell_measurement_theta_min      4.534
_cell_volume                     2578.3(3)
_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-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0662
_diffrn_reflns_av_unetI/netI     0.0550
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            37465
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.498
_diffrn_reflns_theta_min         2.540
_exptl_absorpt_coefficient_mu    0.166
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6462
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.300
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             1064
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.130
_refine_diff_density_max         0.321
_refine_diff_density_min         -0.289
_refine_diff_density_rms         0.051
_refine_ls_abs_structure_details
; 
 Flack x determined using 2693 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   0.02(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     653
_refine_ls_number_reflns         9582
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0841
_refine_ls_R_factor_gt           0.0572
_refine_ls_shift/su_max          0.026
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0853P)^2^+0.1200P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1380
_refine_ls_wR_factor_ref         0.1583
_reflns_Friedel_coverage         0.952
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.997
_reflns_number_gt                6934
_reflns_number_total             9582
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b02795_si_002.cif
_cod_data_source_block           mo_d8v18726_0m
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4036011
_shelx_estimated_absorpt_t_min   0.967
_shelx_estimated_absorpt_t_max   0.979
_shelxl_version_number           2013-4
_shelx_res_checksum              84723
_shelx_hkl_checksum              97297