Nucleophilic Halogenation of Cyclic Nitronates: A General Access to 3-Halo-1,2-Oxazines.
Malykhin, Roman S.; Kokuev, Aleksandr O.; Dorokhov, Valentin S.; Nelyubina, Yulia V.; Tartakovsky, Vladimir A.; Tabolin, Andrey A.; Ioffe, Sema L.; Sukhorukov, Alexey Yu; The Journal of organic chemistry 84 (2019) 13794–13806; doi:10.1021/acs.joc.9b02010

data_4033638
_publ_section_title
;
 Nucleophilic Halogenation of Cyclic Nitronates: A General Access to
 3-Halo-1,2-Oxazines.
;
_journal_issue                   21
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              13794
_journal_page_last               13806
_journal_paper_doi               10.1021/acs.joc.9b02010
_journal_volume                  84
_journal_year                    2019
_chemical_formula_moiety         'C13 H16 N4 O2'
_chemical_formula_sum            'C13 H16 N4 O2'
_chemical_formula_weight         260.30
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_symmetry_Int_Tables_number      61
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_primary     dual
_audit_creation_date             2019-07-04
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   8.6675(2)
_cell_length_b                   13.7568(3)
_cell_length_c                   21.7507(5)
_cell_measurement_reflns_used    9917
_cell_measurement_temperature    120
_cell_measurement_theta_max      67.72
_cell_measurement_theta_min      4.06
_cell_volume                     2593.49(10)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      120
_diffrn_measured_fraction_theta_full 0.9878
_diffrn_measured_fraction_theta_max 0.9878
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0539
_diffrn_reflns_av_unetI/netI     0.0239
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            26868
_diffrn_reflns_theta_full        68.0411
_diffrn_reflns_theta_max         68.04
_diffrn_reflns_theta_min         4.06
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.765
_exptl_absorpt_correction_T_max  0.7530
_exptl_absorpt_correction_T_min  0.3866
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.1345 before and 0.0674 after correction.
The Ratio of minimum to maximum transmission is 0.5134.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.3332
_exptl_crystal_description       plate
_exptl_crystal_F_000             1107.6077
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.2501
_refine_diff_density_min         -0.2486
_refine_diff_density_rms         0.0505
_refine_ls_d_res_high            0.8312
_refine_ls_d_res_low             10.8753
_refine_ls_goodness_of_fit_ref   1.0456
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    25
_refine_ls_number_parameters     175
_refine_ls_number_reflns         2339
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0456
_refine_ls_R_factor_all          0.0433
_refine_ls_R_factor_gt           0.0368
_refine_ls_shift/su_max          0.0002
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0432P)^2^+1.1995P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0887
_refine_ls_wR_factor_ref         0.0940
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              10
_reflns_limit_h_min              0
_reflns_limit_k_max              16
_reflns_limit_k_min              0
_reflns_limit_l_max              25
_reflns_limit_l_min              0
_reflns_number_gt                2045
_reflns_number_total             2339
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            jo9b02010_si_004.cif
_cod_data_source_block           1
_cod_depositor_comments
'Adding full bibliography for 4033636--4033638.cif.'
_cod_database_code               4033638
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C2(H2)
2.b Secondary CH2 refined with riding coordinates:
 C3(H3a,H3b)
2.c Aromatic/amide H refined with riding coordinates:
 C12(H12), C11(H11), C8(H8), C9(H9)
2.d Idealised Me refined as rotating group:
 C6(H6a,H6b,H6c), C5(H5a,H5b,H5c), C13(H13a,H13b,H13c)
;
_olex2_submission_special_instructions 'No special instructions were received'