Bifunctional catalysis in the stereocontrolled synthesis of tetrahydro-1,2-oxazines.
Moczulski, Marek; Drelich, Piotr; Albrecht, Łukasz; Organic & biomolecular chemistry 16 (2018) 376–379; doi:10.1039/c7ob02894f

data_7156026
_publ_section_title
;
 Bifunctional catalysis in the stereocontrolled synthesis of
 tetrahydro-1,2-oxazines.
;
_journal_issue                   3
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              376
_journal_page_last               379
_journal_paper_doi               10.1039/c7ob02894f
_journal_volume                  16
_journal_year                    2018
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C19 H19 N3 O9 S'
_chemical_formula_sum            'C19 H19 N3 O9 S'
_chemical_formula_weight         465.43
_chemical_name_systematic
'Methyl 2-((3R,4S,5S)-4-nitro-2-((2-nitrophenyl)sulfonyl)-3-phenyl-1,2-oxazinan-5-yl)acetate'
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2017-05-30
_audit_creation_method
;
Olex2 1.2-ac3
(compiled 2017.01.05 svn.r3372 for Rigaku Oxford Diffraction, GUI svn.r5289)
;
_audit_update_record
;
2017-05-30 deposited with the CCDC.
2017-12-08 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 93.111(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   5.9946(2)
_cell_length_b                   13.3006(5)
_cell_length_c                   13.1317(5)
_cell_measurement_reflns_used    5603
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      78.9210
_cell_measurement_theta_min      3.3570
_cell_volume                     1045.47(7)
_computing_cell_refinement       'CrysAlisPro 1.171.39.16b (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.16b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.16b (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            'Pilatus 300K'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.962
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -50.00  31.00   0.50    5.00    --  -46.48  38.00  90.00  162
  2  \w   -125.00 -25.00   0.50    5.00    --  -46.48 -19.00-150.00  200
  3  \w   -124.00 -27.00   0.50    5.00    --  -46.48 -38.00 -60.00  194
  4  \w     59.00 121.00   0.50    5.00    --   46.48 178.00-120.00  124
  5  \w    -50.00 -12.00   0.50   20.00    --  -90.25  38.00-120.00   76
  6  \w    -74.00 -16.00   0.50   20.00    --  -90.25  57.00-180.00  116
  7  \w    -74.00 -16.00   0.50   20.00    --  -90.25  57.00-120.00  116
  8  \w    -74.00 -16.00   0.50   20.00    --  -90.25  57.00  60.00  116
  9  \w     33.00 133.00   0.50   20.00    --  111.75 -19.00 150.00  200
 10  \w     34.00  93.00   0.50   20.00    --  111.75 -38.00-180.00  118
 11  \w     99.00 178.00   0.50   20.00    --  111.75 111.00-125.00  158
 12  \w     40.00 110.00   0.50   20.00    --  111.75 -99.00-120.00  140
 13  \w     38.00 122.00   0.50   20.00    --  111.75-125.00-150.00  168
 14  \w     40.00 110.00   0.50   20.00    --  111.75 -99.00  90.00  140
 15  \w     40.00 110.00   0.50   20.00    --  111.75 -99.00-150.00  140
 16  \w     44.00 139.00   0.50   20.00    --  111.75 -77.00 120.00  190
 17  \w     33.00 133.00   0.50   20.00    --  111.75 -19.00 -60.00  200
 18  \w   -114.00 -19.00   0.50    5.00    --  -46.48 -77.00 120.00  190
 19  \w   -124.00 -27.00   0.50    5.00    --  -46.48 -38.00 150.00  194
 20  \w     59.00 100.00   0.50    5.00    --   46.48 178.00  30.00   82
 21  \w     28.00 120.00   0.50    5.00    --   46.48  57.00  60.00  184
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, Pilatus 300K'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0559150000
_diffrn_orient_matrix_UB_12      -0.1125902000
_diffrn_orient_matrix_UB_13      -0.0085565000
_diffrn_orient_matrix_UB_21      -0.0403178000
_diffrn_orient_matrix_UB_22      -0.0139302000
_diffrn_orient_matrix_UB_23      0.1140591000
_diffrn_orient_matrix_UB_31      -0.2479578000
_diffrn_orient_matrix_UB_32      -0.0231831000
_diffrn_orient_matrix_UB_33      -0.0269909000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0548
_diffrn_reflns_av_unetI/netI     0.0467
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.962
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            10198
_diffrn_reflns_point_group_measured_fraction_full 0.904
_diffrn_reflns_point_group_measured_fraction_max 0.835
_diffrn_reflns_theta_full        68.000
_diffrn_reflns_theta_max         79.321
_diffrn_reflns_theta_min         3.371
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.903
_exptl_absorpt_correction_T_max  0.942
_exptl_absorpt_correction_T_min  0.865
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.16b (Rigaku Oxford Diffraction, 2015)
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)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.479
_exptl_crystal_description       prism
_exptl_crystal_F_000             484
_exptl_crystal_size_max          0.148
_exptl_crystal_size_mid          0.051
_exptl_crystal_size_min          0.047
_refine_diff_density_max         0.517
_refine_diff_density_min         -0.485
_refine_diff_density_rms         0.079
_refine_ls_abs_structure_details
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   -0.02(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     290
_refine_ls_number_reflns         3787
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0633
_refine_ls_R_factor_gt           0.0580
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1308P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1566
_refine_ls_wR_factor_ref         0.1609
_reflns_Friedel_coverage         0.662
_reflns_Friedel_fraction_full    0.802
_reflns_Friedel_fraction_max     0.696
_reflns_number_gt                3401
_reflns_number_total             3787
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7ob02894f2.cif
_cod_data_source_block           la_mm_1_71_new
_cod_depositor_comments          'Adding full bibliography for 7156026.cif.'
_cod_database_code               7156026
_shelx_shelxl_version_number     2016/6
_diffrn_oxdiff_ac3_digest_frames
;
01f9bd4fb1a45b21936a4c13f6ac43e98803208ec35
;
_diffrn_oxdiff_ac3_digest_hkl
;
011b72219a2b4391bd6b49ad6d5edeedd3f77e
;
_reflns_odcompleteness_completeness 99.70
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     68.13
_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:
 C6(H6), C1(H1), C5(H5)
2.b Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B), C4(H4A,H4B)
2.c Aromatic/amide H refined with riding coordinates:
 C29(H29), C10(H10), C11(H11), C9(H9), C8(H8), C12(H12), C28(H28), C27(H27),
 C26(H26)
2.d Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C)
;
_shelx_res_checksum              19841
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 4.066
_oxdiff_exptl_absorpt_empirical_full_min 0.543