Conformational Studies of N~3~-Substituted [1,3,4]-Oxadiazinan-2-ones
David M. Casper; Jennifer R. Blackburn; Christopher D. Maroules; Tana Brady; Joel M. Esken; Gregory M. Ferrence; Jean M. Standard; Shawn R. Hitchcock; Journal of Organic Chemistry 67 (2002) 8871–8876; doi:10.1021/jo020322g

data_4022211
_publ_contact_author             'Ferrence, Gregory M.'
_publ_contact_author_email       gferren@ilstu.edu
_publ_section_title
;
 Conformational Studies of N~3~-Substituted [1,3,4]-Oxadiazinan-2-ones
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              8871
_journal_page_last               8876
_journal_paper_doi               10.1021/jo020322g
_journal_volume                  67
_journal_year                    2002
_chemical_compound_source        'Hitchcock Laboratory'
_chemical_formula_moiety         'C14 H18 N2 O3'
_chemical_formula_sum            'C14 H18 N2 O3'
_chemical_formula_weight         262.3
_chemical_name_systematic
;
(5S,6R)-4,5-dimethyl-6-phenyl-3-propionyl-2H-1,3,4-oxadiazin-2-one
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      19
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2002-03-11T16:12:47-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.2571(3)
_cell_length_b                   12.9524(11)
_cell_length_c                   16.9737(14)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      13.3325
_cell_measurement_theta_min      9.9145
_cell_measurement_wavelength     0.71073
_cell_volume                     1375.62(18)
_computing_cell_refinement       'CAD4 Express (Enraf Nonius, 1994)'
_computing_data_collection       'CAD4 Express (Enraf Nonius, 1994)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1995)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR-92 (Altomare, 1993)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'scintillation LiI'
_diffrn_detector_dtime           1.195
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       '\k-geometry diffractometer'
_diffrn_measurement_device_type  'Enraf Nonius CAD4'
_diffrn_measurement_method       'non-profiled omega/2theta scans'
_diffrn_orient_matrix_type
;
  x-axis points to radiation source
  the matrix is specified in reciprocal space
;
_diffrn_orient_matrix_UB_11      -0.57369E-1
_diffrn_orient_matrix_UB_12      0.71453E-1
_diffrn_orient_matrix_UB_13      -0.8705E-2
_diffrn_orient_matrix_UB_21      0.147859
_diffrn_orient_matrix_UB_22      0.02901
_diffrn_orient_matrix_UB_23      0.6303E-2
_diffrn_orient_matrix_UB_31      0.24501E-1
_diffrn_orient_matrix_UB_32      -0.7641E-2
_diffrn_orient_matrix_UB_33      -0.58251E-1
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0132
_diffrn_reflns_av_unetI/netI     0.0146
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            3016
_diffrn_reflns_theta_full        25.87
_diffrn_reflns_theta_max         25.87
_diffrn_reflns_theta_min         1.98
_diffrn_source                   'Enraf Nonius FR590'
_diffrn_standards_decay_%        1
_diffrn_standards_interval_time  120
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.09
_exptl_absorpt_correction_T_max  0.9498
_exptl_absorpt_correction_T_min  0.8862
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details
;
North A.C.T., Phillips D.C. & Mathews F.S. (1968) Acta. Cryst. A24, 351
        Number of psi-scan sets used was   9
        Theta correction was applied.
        Averaged transmission function was used.
        No Fourier smoothing was applied.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.267
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             560
_exptl_crystal_size_max          1.5
_exptl_crystal_size_mid          0.71
_exptl_crystal_size_min          0.32
_refine_diff_density_max         0.1
_refine_diff_density_min         -0.178
_refine_diff_density_rms         0.038
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         2655
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0393
_refine_ls_R_factor_gt           0.0318
_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^)+(0.0530P)^2^+0.1093P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0841
_refine_ls_wR_factor_ref         0.0883
_reflns_number_gt                2404
_reflns_number_total             2655
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo020322g_s1.cif
_cod_data_source_block           gf0009
_cod_database_code               4022211