Synthesis of 1,4-Oxazepane-2,5-diones via Cyclization of Rotationally Restricted Amino Acid Precursors and Structural Reassignment of Serratin.
Ruysbergh, Ewout; Van Hecke, Kristof; Stevens, Christian V.; De Kimpe, Norbert; Mangelinckx, Sven; The Journal of organic chemistry 82 (2017) 6210–6222; doi:10.1021/acs.joc.7b00790

data_4032518
_publ_section_title
;
 Synthesis of 1,4-Oxazepane-2,5-diones via Cyclization of Rotationally
 Restricted Amino Acid Precursors and Structural Reassignment of Serratin.
;
_journal_issue                   12
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              6210
_journal_page_last               6222
_journal_paper_doi               10.1021/acs.joc.7b00790
_journal_volume                  82
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C17 H29 N O4'
_chemical_formula_sum            'C17 H29 N O4'
_chemical_formula_weight         311.41
_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'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2016-02-10
_audit_creation_method
;
Olex2 1.2
(compiled Sep 16 2015 11:44:03 for OlexSys, GUI svn.r5103)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.65117(9)
_cell_length_b                   11.07138(12)
_cell_length_c                   29.0073(4)
_cell_measurement_reflns_used    17520
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.9850
_cell_measurement_theta_min      4.2310
_cell_volume                     1814.88(4)
_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_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4839
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.992
_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   -120.00  -8.00   1.00    1.00    --  -41.93 -24.00-160.00  112
  2  \w     18.00  94.00   1.00    1.00    --   41.93-119.00 127.00   76
  3  \w     97.00 178.00   1.00    4.00    --  109.13 119.00-147.00   81
  4  \w     31.00  95.00   1.00    4.00    --  109.13 -24.00-160.00   64
  5  \w    101.00 178.00   1.00    4.00    --  109.13 102.00 128.00   77
  6  \w    -50.00  32.00   1.00    1.00    --  -41.93  38.00  30.00   82
  7  \w     26.00 109.00   1.00    4.00    --  109.13 -94.00 -30.00   83
  8  \w     33.00  91.00   1.00    4.00    --  109.13 -30.00 150.00   58
  9  \w     33.00  91.00   1.00    4.00    --  109.13 -30.00-120.00   58
 10  \w     33.00  91.00   1.00    4.00    --  109.13 -30.00 -30.00   58
 11  \w    -50.00  32.00   1.00    1.00    --  -41.93  38.00-180.00   82
 12  \w   -115.00 -14.00   1.00    1.00    --  -41.93 -57.00 120.00  101
 13  \w   -115.00 -14.00   1.00    1.00    --  -41.93 -57.00  30.00  101
 14  \w     81.00 178.00   1.00    4.00    --  109.13  30.00  30.00   97
 15  \w     26.00 109.00   1.00    4.00    --  109.13 -94.00-180.00   83
 16  \w     56.00 178.00   1.00    4.00    --  109.13  15.00 -90.00  122
 17  \w     80.00 178.00   1.00    4.00    --  109.13  61.00 150.00   98
 18  \w     81.00 178.00   1.00    4.00    --  109.13  30.00 120.00   97
 19  \w     77.00 178.00   1.00    4.00    --  109.13  77.00 -60.00  101
 20  \w   -118.00  -9.00   1.00    1.00    --  -41.93 -77.00-120.00  109
 21  \w   -118.00  -9.00   1.00    1.00    --  -41.93 -77.00 -30.00  109
 22  \w      1.00  83.00   1.00    1.00    --   41.93 -99.00-120.00   82
 23  \w     36.00 121.00   1.00    4.00    --  109.13-125.00 -60.00   85
 24  \w     80.00 178.00   1.00    4.00    --  109.13  61.00  60.00   98
 25  \w     77.00 178.00   1.00    4.00    --  109.13  77.00-180.00  101
 26  \w     80.00 178.00   1.00    4.00    --  109.13  61.00-120.00   98
 27  \w     80.00 178.00   1.00    4.00    --  109.13  61.00 120.00   98
 28  \w     80.00 178.00   1.00    4.00    --  109.13  61.00 -90.00   98
 29  \w   -118.00  -9.00   1.00    1.00    --  -41.93 -77.00 120.00  109
 30  \w      9.00 118.00   1.00    1.00    --   41.93  77.00-120.00  109
 31  \w     17.00 116.00   1.00    1.00    --   41.93  38.00  30.00   99
 32  \w     80.00 178.00   1.00    4.00    --  109.13  61.00 -60.00   98
 33  \w     80.00 178.00   1.00    4.00    --  109.13  61.00 -30.00   98
 34  \w     80.00 178.00   1.00    4.00    --  109.13  61.00-180.00   98
 35  \w     83.00 178.00   1.00    4.00    --  109.13  45.00-120.00   95
 36  \w     77.00 178.00   1.00    4.00    --  109.13  77.00  90.00  101
 37  \w     80.00 178.00   1.00    4.00    --  109.13  61.00  30.00   98
 38  \w   -115.00 -14.00   1.00    1.00    --  -41.93 -57.00   0.00  101
 39  \w      9.00 118.00   1.00    1.00    --   41.93  77.00  30.00  109
 40  \w     23.00  98.00   1.00    1.00    --   41.93-125.00   0.00   75
 41  \w     77.00 178.00   1.00    4.00    --  109.13  77.00 -90.00  101
 42  \w     80.00 178.00   1.00    4.00    --  109.13  61.00   0.00   98
 43  \w     80.00 178.00   1.00    4.00    --  109.13  61.00  90.00   98
 44  \w     77.00 178.00   1.00    4.00    --  109.13  77.00 120.00  101
 45  \w     77.00 178.00   1.00    4.00    --  109.13  77.00  30.00  101
 46  \w     33.00 142.00   1.00    4.00    --  109.13 -77.00  30.00  109
 47  \w   -116.00 -17.00   1.00    1.00    --  -41.93 -38.00 120.00   99
 48  \w     14.00 115.00   1.00    1.00    --   41.93  57.00  30.00  101
 49  \w     14.00 115.00   1.00    1.00    --   41.93  57.00 -60.00  101
 50  \w     77.00 178.00   1.00    4.00    --  109.13  77.00  60.00  101
 51  \w     77.00 178.00   1.00    4.00    --  109.13  77.00-120.00  101
 52  \w     77.00 178.00   1.00    4.00    --  109.13  77.00 150.00  101
 53  \w     77.00 178.00   1.00    4.00    --  109.13  77.00 -30.00  101
 54  \w     80.00 178.00   1.00    4.00    --  109.13  61.00-150.00   98
 55  \w     77.00 178.00   1.00    4.00    --  109.13  77.00   0.00  101
 56  \w   -118.00  -9.00   1.00    1.00    --  -41.93 -77.00-180.00  109
 57  \w    -46.00  43.00   1.00    1.00    --   41.93   0.00-180.00   89
 58  \w      9.00 118.00   1.00    1.00    --   41.93  77.00 -60.00  109
;
_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      -0.0110344000
_diffrn_orient_matrix_UB_12      -0.0289320000
_diffrn_orient_matrix_UB_13      0.0519121000
_diffrn_orient_matrix_UB_21      0.0855535000
_diffrn_orient_matrix_UB_22      -0.1295888000
_diffrn_orient_matrix_UB_23      -0.0098280000
_diffrn_orient_matrix_UB_31      0.2585374000
_diffrn_orient_matrix_UB_32      0.0416543000
_diffrn_orient_matrix_UB_33      0.0054731000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0826
_diffrn_reflns_av_unetI/netI     0.0217
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_number            62469
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.277
_diffrn_reflns_theta_min         4.274
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.647
_exptl_absorpt_correction_T_max  0.991
_exptl_absorpt_correction_T_min  0.970
_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    1.140
_exptl_crystal_description       'rect. Prism'
_exptl_crystal_F_000             680
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.112
_exptl_crystal_size_min          0.091
_refine_diff_density_max         0.128
_refine_diff_density_min         -0.200
_refine_diff_density_rms         0.036
_refine_ls_abs_structure_details
;
 Flack x determined using 1118 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   -0.03(12)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         3718
_refine_ls_number_restraints     22
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0617
_refine_ls_R_factor_gt           0.0531
_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^)+(0.1058P)^2^+0.0464P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1487
_refine_ls_wR_factor_ref         0.1624
_reflns_Friedel_coverage         0.706
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.990
_reflns_number_gt                3083
_reflns_number_total             3718
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo7b00790_si_002.cif
_cod_data_source_block           sm012
_cod_depositor_comments          'Adding full bibliography for 4032518.cif.'
_cod_database_code               4032518
_shelxl_version_number           2013-4
_chemical_oxdiff_formula         'C10 H10 N2 O2'
_reflns_odcompleteness_completeness 99.95
_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, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C1-C12 = C12-C13 = C13-C14A = C14A-C15A = C15A-C16A = C16A-C17A
 1.52 with sigma of 0.01
 C1-C12 = C12-C13 = C13-C14B = C14B-C15B = C15B-C16B = C16B-C17B
 1.52 with sigma of 0.01
 C1-C13 = C12-C14A = C13-C15A = C14A-C16A = C15A-C17A
 2.54 with sigma of 0.02
 C1-C13 = C12-C14B = C13-C15B = C14B-C16B = C15B-C17B
 2.54 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C14A) = Uanis(C14B)
Uanis(C15A) = Uanis(C15B)
Uanis(C16A) = Uanis(C16B)
Uanis(C17A) = Uanis(C17B)
4. Others
 Sof(H13C)=Sof(H13D)=Sof(C14B)=Sof(H14C)=Sof(H14D)=Sof(C15B)=Sof(H15C)=
 Sof(H15D)=Sof(C16B)=Sof(H16C)=Sof(H16D)=Sof(C17B)=Sof(H17D)=Sof(H17E)=
 Sof(H17F)=1-FVAR(1)
 Sof(H13A)=Sof(H13B)=Sof(C14A)=Sof(H14A)=Sof(H14B)=Sof(C15A)=Sof(H15A)=
 Sof(H15B)=Sof(C16A)=Sof(H16A)=Sof(H16B)=Sof(C17A)=Sof(H17A)=Sof(H17B)=
 Sof(H17C)=FVAR(1)
5.a Ternary CH refined with riding coordinates:
 C1(H1), C4(H4), C6(H6)
5.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C7(H7A,H7B), C12(H12A,H12B), C13(H13A,H13B), C13(H13C,H13D),
 C14A(H14A,H14B), C15A(H15A,H15B), C16A(H16A,H16B), C14B(H14C,H14D), C15B(H15C,
 H15D), C16B(H16C,H16D)
5.c Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C10(H10A,H10B,H10C), C11(H11A,H11B,H11C), C17A(H17A,H17B,
 H17C), C17B(H17D,H17E,H17F)
;
_shelx_res_checksum              56339
_shelx_hkl_checksum              6834
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.543
_oxdiff_exptl_absorpt_empirical_full_min 0.547