Expedient Metal-Free Synthesis of 1,3-Oxazinen-4-ones.
Craig, Alexander J.; van der Salm, Louise; Stevens-Cullinane, Lars; Lucas, Nigel T.; Tan, Eng Wui; Hawkins, Bill C.; Organic letters 17 (2015) 234–237; doi:10.1021/ol503350h

data_1518483
_publ_section_title
;
 Expedient Metal-Free Synthesis of 1,3-Oxazinen-4-ones.
;
_journal_issue                   2
_journal_name_full               'Organic letters'
_journal_page_first              234
_journal_page_last               237
_journal_paper_doi               10.1021/ol503350h
_journal_volume                  17
_journal_year                    2015
_chemical_formula_moiety         'C23 H24 Cl N O4'
_chemical_formula_sum            'C23 H24 Cl N O4'
_chemical_formula_weight         413.88
_chemical_name_systematic
; 
5-(2-chloroethyl)-2,2-diphenyl-3-(methylcarbonyloxyethyl)-6-methyl-
1,3-oxazinen-4-one 
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_block_code                ntl1408
_audit_creation_method           SHELXL-97
_cell_angle_alpha                67.347(6)
_cell_angle_beta                 70.617(5)
_cell_angle_gamma                79.738(5)
_cell_formula_units_Z            2
_cell_length_a                   10.0098(5)
_cell_length_b                   10.1777(7)
_cell_length_c                   12.0505(7)
_cell_measurement_reflns_used    5107
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      74.4510
_cell_measurement_theta_min      4.7260
_cell_volume                     1066.95(12)
_computing_cell_refinement       'CrysAlisPro (Agilent, V 1.171.36.28)'
_computing_data_collection       'CrysAlisPro (Agilent, V 1.171.36.28)'
_computing_data_reduction        'CrysAlisPro (Agilent, V 1.171.36.28)'
_computing_molecular_graphics    'Mercury (CCDC, 2013)'
_computing_publication_material  'enCIFer (CCDC, 2011)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_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 0.997
_diffrn_measured_fraction_theta_max 0.957
_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           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0204
_diffrn_reflns_av_sigmaI/netI    0.0273
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            7123
_diffrn_reflns_theta_full        67.00
_diffrn_reflns_theta_max         74.35
_diffrn_reflns_theta_min         4.69
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.821
_exptl_absorpt_correction_T_max  0.793
_exptl_absorpt_correction_T_min  0.645
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies, Version 1.171.36.28
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.288
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       irregular
_exptl_crystal_F_000             436
_exptl_crystal_preparation
;
Crystals were grown by slow evaporation of dichloromethane/petroleum ether 
at room temperature.
;
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.297
_refine_diff_density_min         -0.354
_refine_diff_density_rms         0.043
_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     264
_refine_ls_number_reflns         4169
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0383
_refine_ls_R_factor_gt           0.0341
_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^)+(0.0420P)^2^+0.3679P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0848
_refine_ls_wR_factor_ref         0.0890
_reflns_number_gt                3731
_reflns_number_total             4169
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol503350h_si_001.cif
_cod_data_source_block           7a
_cod_depositor_comments          'Adding full bibliography for 1518483.cif.'
_cod_original_cell_volume        1066.96(11)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               1518483