One-Step Assembly of Functionalized Morpholinones and 1,4-Oxazepane-3-ones via [3+3]- and [3+4]-Annulation of Aza-oxyallyl Cation and Amphoteric Compounds.
Bera, Tishyasoumya; Singh, Bandana; Hamlin, Trevor A.; Sahoo, Subash C.; Saha, Jaideep; The Journal of organic chemistry  (2019) –; doi:10.1021/acs.joc.9b02269

data_4036098
_publ_section_title
;
 One-Step Assembly of Functionalized Morpholinones and
 1,4-Oxazepane-3-ones via [3+3]- and [3+4]-Annulation of Aza-oxyallyl
 Cation and Amphoteric Compounds.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.9b02269
_journal_year                    2019
_chemical_absolute_configuration syn
_chemical_formula_moiety         '	C22 H25 N O4'
_chemical_formula_sum            'C22 H25 N O4'
_chemical_formula_weight         367.43
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2019-06-29
_audit_creation_method
;
Olex2 1.2-ac3
(compiled 2017.02.24 svn.r3390 for Rigaku Oxford Diffraction, GUI svn.r5318)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   7.7239(2)
_cell_length_b                   21.0831(7)
_cell_length_c                   23.9339(9)
_cell_measurement_reflns_used    13909
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      21.9150
_cell_measurement_theta_min      3.2740
_cell_volume                     3897.5(2)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_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    'SIR2004 (Burla et al., 2007)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.963
_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    -56.00 -31.00   0.50   25.00    --   -9.79 127.00 165.00   50
  2  \w    -42.00 -17.00   0.50   25.00    --   -9.79 144.00 -25.00   50
  3  \w     17.00  42.00   0.50   25.00    --   10.07-144.00 -79.00   50
  4  \w     24.00  50.00   0.50   25.00    --   10.07-127.00  89.00   52
  5  \w    -59.00 -20.00   0.50   25.00    --   -9.79 -57.00-180.00   78
  6  \w    -47.00 -21.00   0.50   25.00    --   -9.79 125.00-120.00   52
  7  \w    -23.00  45.00   0.50   25.00    --   -9.79  38.00-150.00  136
  8  \w    -23.00  14.00   0.50   25.00    --   -9.79  38.00-180.00   74
  9  \w     24.00  59.00   0.50   25.00    --   -9.79  19.00-120.00   70
 10  \w    -22.00  34.00   0.50   25.00    --   -9.79  38.00 120.00  112
 11  \w    -10.00  16.00   0.50   25.00    --   -9.79  19.00-120.00   52
 12  \w    -73.00 -12.00   0.50   25.00    --   -9.79 -19.00-120.00  122
 13  \w    -70.00  10.00   0.50   25.00    --   -9.79 -77.00  30.00  160
 14  \w    -12.00  75.00   0.50   25.00    --   10.07  77.00-120.00  174
 15  \w    -38.00  -3.00   0.50   25.00    --   10.07 125.00 -14.53   70
 16  \w    -15.00  41.00   0.50   25.00    --   10.07  77.00 -30.00  112
 17  \w    -52.00  -8.00   0.50   25.00    --   10.07 -57.00  90.00   88
 18  \w    -54.00 -29.00   0.50   25.00    --   10.07 -77.00   0.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'SuperNova, Single source at offset/far, HyPix3000'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0130057000
_diffrn_orient_matrix_UB_12      0.0265058000
_diffrn_orient_matrix_UB_13      -0.0177794000
_diffrn_orient_matrix_UB_21      -0.0013589000
_diffrn_orient_matrix_UB_22      0.0203012000
_diffrn_orient_matrix_UB_23      0.0236102000
_diffrn_orient_matrix_UB_31      0.0909195000
_diffrn_orient_matrix_UB_32      0.0040816000
_diffrn_orient_matrix_UB_33      -0.0021602000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1200
_diffrn_reflns_av_unetI/netI     0.0796
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.963
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            55214
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.949
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.465
_diffrn_reflns_theta_min         3.202
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.51302
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.252
_exptl_crystal_description       plate
_exptl_crystal_F_000             1568
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.379
_refine_diff_density_min         -0.238
_refine_diff_density_rms         0.062
_refine_ls_abs_structure_details
;
 Flack x determined using 1337 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -1.0(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.956
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     491
_refine_ls_number_reflns         8443
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.956
_refine_ls_R_factor_all          0.1579
_refine_ls_R_factor_gt           0.0807
_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^)+(0.1392P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1928
_refine_ls_wR_factor_ref         0.2399
_reflns_Friedel_coverage         0.755
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.930
_reflns_number_gt                4121
_reflns_number_total             8443
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b02269_si_002.cif
_cod_data_source_block           8aa
_cod_original_formula_sum        '	C22 H25 N O4'
_cod_database_code               4036098
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H N O'
_diffrn_oxdiff_ac3_digest_frames
;
01f89be6ff54d145debc75f6bfb0cc8ede00025f524
;
_diffrn_oxdiff_ac3_digest_hkl
;
018a7a2208d39022bf7180651a26ce28a454b5
;
_reflns_odcompleteness_completeness 99.62
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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:
 C7(H7), C7A(H7A)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C8A(H8AA,H8AB), C5(H5A,H5B), C6(H6A,H6B), C16A(H16A,H16B),
 C16(H16C,H16D), C6A(H6AA,H6AB), C5A(H5AA,H5AB)
2.c Aromatic/amide H refined with riding coordinates:
 C22A(H22A), C15(H15), C22(H22), C18A(H18A), C11(H11), C15A(H15A), C21(H21),
 C14(H14), C11A(H11A), C18(H18), C12(H12), C20(H20), C13A(H13A), C14A(H14A),
 C13(H13), C19A(H19A), C20A(H20A), C21A(H21A), C19(H19), C12A(H12A)
2.d Idealised Me refined as rotating group:
 C4(H4A,H4B,H4C), C3A(H3AA,H3AB,H3AC), C3(H3A,H3B,H3C), C4A(H4AA,H4AB,H4AC)
;
_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
;
_oxdiff_exptl_absorpt_empirical_full_max 1.851
_oxdiff_exptl_absorpt_empirical_full_min 0.512