The Elusive Seven-Membered Cyclic Imino Ether Tetrahydrooxazepine.
Verbraeken, Bart; Hullaert, Jan; van Guyse, Joachim; Van Hecke, Kristof; Winne, Johan; Hoogenboom, Richard; Journal of the American Chemical Society 140 (2018) 17404–17408; doi:10.1021/jacs.8b10918

data_4133545
_publ_section_title
;
 The Elusive Seven-Membered Cyclic Imino Ether Tetrahydrooxazepine.
;
_journal_issue                   50
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              17404
_journal_page_last               17408
_journal_paper_doi               10.1021/jacs.8b10918
_journal_volume                  140
_journal_year                    2018
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C10 H13 N O S'
_chemical_formula_sum            'C10 H13 N O S'
_chemical_formula_weight         195.27
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2018-03-01
_audit_creation_method
;
Olex2 1.2
(compiled Aug 10 2017 17:28:52 for OlexSys, GUI svn.r5381)
;
_cell_angle_alpha                90
_cell_angle_beta                 99.2411(17)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.45000(12)
_cell_length_b                   10.41727(14)
_cell_length_c                   14.8501(2)
_cell_measurement_reflns_used    10145
_cell_measurement_temperature    100.0(1)
_cell_measurement_theta_max      75.1370
_cell_measurement_theta_min      5.1710
_cell_volume                     984.85(3)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.0(1)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4839
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.991
_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    -82.00  22.00   1.00    1.00    --  -41.68  97.00  62.00  104
  2  \w     -1.00  82.00   1.00    1.00    --   41.68 -97.00 -45.00   83
  3  \w    101.00 178.00   1.00    3.00    --  109.13  97.00  62.00   77
  4  \w     28.00 110.00   1.00    3.00    --  109.13 -97.00 -45.00   82
  5  \w   -116.00 -17.00   1.00    1.00    --  -41.68 -38.00 120.00   99
  6  \w   -115.00 -14.00   1.00    1.00    --  -41.68 -57.00-120.00  101
  7  \w    -70.00  31.00   1.00    1.00    --  -41.68  57.00 -90.00  101
  8  \w     23.00  98.00   1.00    1.00    --   41.68-125.00-180.00   75
  9  \w     94.00 178.00   1.00    3.00    --  109.13 125.00   0.00   84
 10  \w     94.00 178.00   1.00    3.00    --  109.13 125.00  60.00   84
 11  \w     33.00 137.00   1.00    3.00    --  109.13 -30.00   0.00  104
 12  \w     81.00 178.00   1.00    3.00    --  109.13  30.00-150.00   97
 13  \w     36.00 121.00   1.00    3.00    --  109.13-125.00-120.00   85
 14  \w     26.00 109.00   1.00    3.00    --  109.13 -94.00  30.00   83
 15  \w     80.00 178.00   1.00    3.00    --  109.13  61.00 -60.00   98
 16  \w     33.00 137.00   1.00    3.00    --  109.13 -30.00 -90.00  104
 17  \w     83.00 178.00   1.00    3.00    --  109.13  45.00 150.00   95
 18  \w     33.00 142.00   1.00    3.00    --  109.13 -77.00  90.00  109
 19  \w   -115.00 -14.00   1.00    1.00    --  -41.68 -57.00  60.00  101
 20  \w   -118.00  -9.00   1.00    1.00    --  -41.68 -77.00-180.00  109
 21  \w   -115.00 -14.00   1.00    1.00    --  -41.68 -57.00   0.00  101
 22  \w   -118.00  -9.00   1.00    1.00    --  -41.68 -77.00 -30.00  109
 23  \w   -118.00  -9.00   1.00    1.00    --  -41.68 -77.00-150.00  109
 24  \w      9.00 118.00   1.00    1.00    --   41.68  77.00 120.00  109
 25  \w     81.00 178.00   1.00    3.00    --  109.13  30.00  30.00   97
 26  \w     80.00 178.00   1.00    3.00    --  109.13  61.00-150.00   98
 27  \w     77.00 178.00   1.00    3.00    --  109.13  77.00  90.00  101
 28  \w     77.00 178.00   1.00    3.00    --  109.13  77.00  30.00  101
 29  \w     80.00 178.00   1.00    3.00    --  109.13  61.00 -30.00   98
 30  \w     81.00 178.00   1.00    3.00    --  109.13  30.00 -90.00   97
 31  \w     80.00 178.00   1.00    3.00    --  109.13  61.00 -90.00   98
 32  \w     83.00 178.00   1.00    3.00    --  109.13  45.00  90.00   95
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0897981000
_diffrn_orient_matrix_UB_12      -0.1367828000
_diffrn_orient_matrix_UB_13      -0.0147223000
_diffrn_orient_matrix_UB_21      0.0456658000
_diffrn_orient_matrix_UB_22      -0.0237006000
_diffrn_orient_matrix_UB_23      0.1036967000
_diffrn_orient_matrix_UB_31      -0.2200009000
_diffrn_orient_matrix_UB_32      0.0509531000
_diffrn_orient_matrix_UB_33      0.0089622000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0373
_diffrn_reflns_av_unetI/netI     0.0241
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            18490
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.409
_diffrn_reflns_theta_min         3.015
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.581
_exptl_absorpt_correction_T_max  0.955
_exptl_absorpt_correction_T_min  0.895
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.317
_exptl_crystal_description       plate
_exptl_crystal_F_000             416
_exptl_crystal_size_max          0.305
_exptl_crystal_size_mid          0.173
_exptl_crystal_size_min          0.104
_refine_diff_density_max         0.199
_refine_diff_density_min         -0.302
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details
;
 Flack x determined using 1708 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   -0.022(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         3987
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0294
_refine_ls_R_factor_gt           0.0278
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0477P)^2^+0.0762P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0742
_refine_ls_wR_factor_ref         0.0755
_reflns_Friedel_coverage         0.869
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.966
_reflns_number_gt                3796
_reflns_number_total             3987
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja8b10918_si_004.cif
_cod_data_source_block           rh080
_cod_database_code               4133545
_shelxl_version_number           2013-4
_chemical_oxdiff_formula         'C10 H13 N O S'
_reflns_odcompleteness_completeness 99.89
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B), C5(H5A,H5B), C12(H12A,H12B), C13(H13A,
 H13B), C14(H14A,H14B), C15(H15A,H15B)
2.b Aromatic/amide H refined with riding coordinates:
 C8(H8), C9(H9), C18(H18), C19(H19)
2.c Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C20(H20A,H20B,H20C)
;
_shelx_res_checksum              19286
_shelx_hkl_checksum              41374
_olex2_exptl_crystal_mounting_method 'mounted on a nylon loop'
_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 1.933
_oxdiff_exptl_absorpt_empirical_full_min 0.696