Ruthenium(II)-Catalyzed Enantioselective γ-Lactams Formation by Intramolecular C-H Amidation of 1,4,2-Dioxazol-5-ones.
Xing, Qi; Chan, Chun-Ming; Yeung, Yiu-Wai; Yu, Wing-Yiu; Journal of the American Chemical Society 141 (2019) 3849–3853; doi:10.1021/jacs.9b00535

data_4128515
_publ_section_title
;
 Ruthenium(II)-Catalyzed Enantioselective \g-Lactams Formation by
 Intramolecular C-H Amidation of 1,4,2-Dioxazol-5-ones.
;
_journal_issue                   9
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              3849
_journal_page_last               3853
_journal_paper_doi               10.1021/jacs.9b00535
_journal_volume                  141
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C11 H11 N O'
_chemical_formula_sum            'C11 H11 N O'
_chemical_formula_weight         173.21
_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     dual
_audit_creation_date             2018-11-07
_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            4
_cell_length_a                   5.41264(14)
_cell_length_b                   5.94200(14)
_cell_length_c                   26.9046(6)
_cell_measurement_reflns_used    4645
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      73.2810
_cell_measurement_theta_min      4.9730
_cell_volume                     865.30(4)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (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_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.990
_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     27.00 109.00   1.00    1.00    --   41.11  57.00   0.00   82
  2  \w    128.00 154.00   1.00    1.00    --  106.95 125.00   0.00   26
  3  \w    142.00 174.00   1.00    1.00    --  106.95 125.00 120.00   32
  4  \w     99.00 158.00   1.00    1.00    --  106.95  30.00 120.00   59
  5  \w     82.00 177.00   1.00    1.00    --  106.95  30.00  30.00   95
  6  \w     58.00 108.00   1.00    1.00    --  106.95 -95.00-150.00   50
  7  \w     57.00 126.00   1.00    1.00    --  106.95 -77.00-120.00   69
  8  \w     37.00 111.00   1.00    1.00    --  106.95 -30.00 -30.00   74
  9  \w     42.00  81.00   1.00    1.00    --  106.95 -95.00  60.00   39
 10  \w     41.00 130.00   1.00    1.00    --  106.95 -45.00  90.00   89
 11  \w     48.00 119.00   1.00    1.00    --  106.95-125.00 150.00   71
 12  \w     14.00 112.00   1.00    1.00    --   41.11  57.00 -90.00   98
 13  \w     31.00 126.00   1.00    1.00    --  106.95 -30.00-150.00   95
 14  \w     25.00  60.00   1.00    1.00    --   41.11-125.00-150.00   35
 15  \w   -100.00 -73.00   1.00    1.00    --  -41.11-140.00  47.00   27
 16  \w    -92.00  -2.00   1.00    1.00    --  -41.11 125.00  30.00   90
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.2353857000
_diffrn_orient_matrix_UB_12      -0.1336828000
_diffrn_orient_matrix_UB_13      0.0128229000
_diffrn_orient_matrix_UB_21      -0.0482015000
_diffrn_orient_matrix_UB_22      0.0388867000
_diffrn_orient_matrix_UB_23      0.0557900000
_diffrn_orient_matrix_UB_31      -0.1524952000
_diffrn_orient_matrix_UB_32      -0.2186500000
_diffrn_orient_matrix_UB_33      0.0020409000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0252
_diffrn_reflns_av_unetI/netI     0.0205
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            5174
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.473
_diffrn_reflns_theta_min         6.581
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.681
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.78049
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.330
_exptl_crystal_description       block
_exptl_crystal_F_000             368
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.187
_refine_diff_density_min         -0.223
_refine_diff_density_rms         0.046
_refine_ls_abs_structure_details
;
 Flack x determined using 650 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.00(11)
_refine_ls_extinction_coef       0.060(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     119
_refine_ls_number_reflns         1706
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.068
_refine_ls_R_factor_all          0.0360
_refine_ls_R_factor_gt           0.0358
_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^)+(0.0592P)^2^+0.2117P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0928
_refine_ls_wR_factor_ref         0.0930
_reflns_Friedel_coverage         0.625
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.972
_reflns_number_gt                1691
_reflns_number_total             1706
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja9b00535_si_002.cif
_cod_data_source_block           xq_1
_cod_database_code               4128515
_shelx_shelxl_version_number     2017/1
_reflns_odcompleteness_completeness 99.80
_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 N(H) groups
2.a Ternary CH refined with riding coordinates:
 C8(H8), C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C7(H7A,H7B)
2.c Aromatic/amide H refined with riding coordinates:
 N1(H1), C5(H5), C2(H2), C3(H3), C4(H4)
;
_shelx_res_checksum              12935
_shelx_hkl_checksum              89398
_olex2_date_sample_data_collection 2018-11-07
_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 1.599
_oxdiff_exptl_absorpt_empirical_full_min 0.660