Nucleophilic Addition onto Methyl-4H-1,4-oxazine-3-carboxylate Moiety: Short Access to 1,4-Diazine Privileged Substructures
Elise Claveau; Isabelle Gillaizeau; Justyna Kalinowska-Tluscik; Pascal Bouyssou; Gérard Coudert; Journal of Organic Chemistry 74 (2009) 2911–2914; doi:10.1021/jo900291f

data_4024462
_publ_section_title
;
Nucleophilic Addition onto Methyl-4H-1,4-oxazine-3-carboxylate Moiety:
Short Access to 1,4-Diazine Privileged Substructures
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              2911
_journal_page_last               2914
_journal_paper_doi               10.1021/jo900291f
_journal_volume                  74
_journal_year                    2009
_chemical_formula_moiety         'C18 H24 N2 O5, H2 O'
_chemical_formula_sum            'C18 H26 N2 O6'
_chemical_formula_weight         366.41
_chemical_name_common            'Compound ec546'
_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_date             2008-07-17T02:16:43-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 105.4699(12)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.2955(4)
_cell_length_b                   8.3964(2)
_cell_length_c                   16.8240(5)
_cell_measurement_reflns_used    9334
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      30.034
_cell_measurement_theta_min      0.998
_cell_volume                     1946.24(9)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor1997)'
_computing_data_collection       'Collect (Nonius BV, 1997-2000)'
_computing_data_reduction
'HKL Denzo and Scalepack (Otwinowski & Minor1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia,1997)'
_computing_publication_material  'WinGX publication routines (Farrugia,1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device       '95mm CCD camera on \k-goniostat'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       CCD
_diffrn_orient_matrix_type       'by Nonius Collect from scalepack cell'
_diffrn_orient_matrix_UB_11      0.0401021
_diffrn_orient_matrix_UB_12      -0.0577947
_diffrn_orient_matrix_UB_13      -0.0961046
_diffrn_orient_matrix_UB_21      -0.020816
_diffrn_orient_matrix_UB_22      -0.0630763
_diffrn_orient_matrix_UB_23      0.0292605
_diffrn_orient_matrix_UB_31      -0.0580401
_diffrn_orient_matrix_UB_32      -0.0085908
_diffrn_orient_matrix_UB_33      -0.0190036
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0358
_diffrn_reflns_av_unetI/netI     0.0464
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            10579
_diffrn_reflns_theta_full        29.97
_diffrn_reflns_theta_max         29.97
_diffrn_reflns_theta_min         2.84
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_T_max  0.99
_exptl_absorpt_correction_T_min  0.97
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
HKL Denzo and Scalepack (Otwinowski & Minor 1997)
;
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.25
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             784
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.297
_refine_diff_density_min         -0.201
_refine_diff_density_rms         0.04
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     313
_refine_ls_number_reflns         5626
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.065
_refine_ls_R_factor_all          0.11
_refine_ls_R_factor_gt           0.0637
_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^)+(0.0591P)^2^+0.6374P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.139
_refine_ls_wR_factor_ref         0.1605
_reflns_number_gt                3631
_reflns_number_total             5626
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo900291f_si_002.cif
_cod_data_source_block           ec546
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               4024462