The Synthesis of Multifunctionalized 1,3-Oxazin-4-ones from Donor-Acceptor Cyclopropanes.
Smith, Robert J.; Mills, Daniel A.; Nhu, Duong; Tan, Eng Wui; Lucas, Nigel T.; Hawkins, Bill C.; The Journal of organic chemistry 81 (2016) 2099–2105; doi:10.1021/acs.joc.6b00112

data_4036632
_publ_section_title
;
 The Synthesis of Multifunctionalized 1,3-Oxazin-4-ones from
 Donor-Acceptor Cyclopropanes.
;
_journal_issue                   5
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              2099
_journal_page_last               2105
_journal_paper_doi               10.1021/acs.joc.6b00112
_journal_volume                  81
_journal_year                    2016
_chemical_formula_moiety         'C25 H26 Cl N O4'
_chemical_formula_sum            'C25 H26 Cl N O4'
_chemical_formula_weight         439.92
_chemical_name_systematic
; 
5-(2-Chlorobut-3-enyl)-2,2-diphenyl-3-(methylcarbonyloxyethyl)-6-methyl-
1,3-oxazinen-4-one 
;
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_block_code                ntl1513_BCH_rjs2-12
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 116.227(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.5568(2)
_cell_length_b                   16.7624(2)
_cell_length_c                   12.9551(2)
_cell_measurement_reflns_used    11277
_cell_measurement_temperature    100(1)
_cell_measurement_theta_max      74.718
_cell_measurement_theta_min      4.267
_cell_volume                     2251.29(7)
_computing_cell_refinement       'CrysAlisPro (Agilent, V 1.171.37.33)'
_computing_data_collection       'CrysAlisPro (Agilent, V 1.171.37.33)'
_computing_data_reduction        'CrysAlisPro (Agilent, V 1.171.37.33)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 2008)'
_computing_publication_material  'enCIFer (CCDC, 2014)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      100(1)
_diffrn_crystal_treatment
; 
Crystal was attached with Paratone N oil to a 0.3 mm CryoLoop supported 
in a copper mounting pin, then quenched in a cold nitrogen gas from a gas
stream from an Oxford Cryosystems Cryostream.
;
_diffrn_detector_area_resol_mean 5.1725
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.956
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_source         'SuperNova (Cu) X-ray Source'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0232
_diffrn_reflns_av_sigmaI/netI    0.0181
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            17233
_diffrn_reflns_theta_full        67.00
_diffrn_reflns_theta_max         74.85
_diffrn_reflns_theta_min         4.28
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.758
_exptl_absorpt_correction_T_max  0.7784
_exptl_absorpt_correction_T_min  0.6777
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies, V 1.171.37.33.
Numerical absorption correction based on gaussian integration over a 
multifaceted crystal model. Empirical absorption correction using 
spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.298
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             928
_exptl_crystal_preparation
;
Crystals were grown by evaporation of a DCM/petroleum solution at 4 degrees.
;
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.727
_refine_diff_density_min         -0.916
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     306
_refine_ls_number_reflns         4425
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0489
_refine_ls_R_factor_gt           0.0466
_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^)+(0.0339P)^2^+2.1025P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1031
_refine_ls_wR_factor_ref         0.1046
_reflns_number_gt                4195
_reflns_number_total             4425
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo6b00112_si_001.cif
_cod_data_source_block           11
_cod_original_cell_volume        2251.29(6)
_cod_original_sg_symbol_H-M      P21/n
_cod_database_code               4036632