Synthesis of N-alkoxy amines and hydroxylamines via the iridium-catalyzed transfer hydrogenation of oximes
Xia, Yanping; Wang, Sen; Miao, Rui; Liao, Jianhua; Ouyang, Lu; Luo, Renshi; Organic & Biomolecular Chemistry  (2022) –; doi:10.1039/D2OB01084D

data_7158788
_publ_section_title
;
 Synthesis of N-alkoxy amines and hydroxylamines via the iridium-catalyzed
 transfer hydrogenation of oximes
;
_journal_name_full               'Organic &amp; Biomolecular Chemistry'
_journal_paper_doi               10.1039/D2OB01084D
_journal_year                    2022
_chemical_formula_moiety         'C19 H19 N O'
_chemical_formula_sum            'C19 H19 N O'
_chemical_formula_weight         277.35
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2021-11-22
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2021-11-22 deposited with the CCDC.	2022-07-15 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 91.477(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.7379(3)
_cell_length_b                   8.2844(5)
_cell_length_c                   31.6487(19)
_cell_measurement_reflns_used    2660
_cell_measurement_temperature    149.99(10)
_cell_measurement_theta_max      73.5270
_cell_measurement_theta_min      5.5010
_cell_volume                     1503.92(15)
_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 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      149.99(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 0.962
_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    -51.00  34.00   1.00    1.00    --  -40.73  38.00 -30.00   85
  2  \w     16.00 111.00   1.00    1.00    --   40.73  38.00 120.00   95
  3  \w     76.00 176.00   1.00    1.00    --  107.58  77.00  90.00  100
  4  \w     92.00 170.00   1.00    1.00    --  107.58  61.00   0.00   78
  5  \w     82.00 154.00   1.00    1.00    --  107.58 146.00-101.00   72
  6  \w     25.00  98.00   1.00    1.00    --  107.58 -95.00 -90.00   73
  7  \w     47.00  79.00   1.00    1.00    --   40.73 -99.00 -90.00   32
  8  \w     39.00  64.00   1.00    1.00    --   40.73 -99.00 120.00   25
  9  \w     36.00 118.00   1.00    1.00    --  107.58-125.00 120.00   82
;
_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      -0.1213926000
_diffrn_orient_matrix_UB_12      0.1120873000
_diffrn_orient_matrix_UB_13      0.0314768000
_diffrn_orient_matrix_UB_21      0.0713729000
_diffrn_orient_matrix_UB_22      0.1479014000
_diffrn_orient_matrix_UB_23      -0.0261739000
_diffrn_orient_matrix_UB_31      -0.2287182000
_diffrn_orient_matrix_UB_32      -0.0133252000
_diffrn_orient_matrix_UB_33      -0.0263132000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0397
_diffrn_reflns_av_unetI/netI     0.0498
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.962
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_number            5434
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.962
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.752
_diffrn_reflns_theta_min         2.793
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.584
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.41923
_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    1.225
_exptl_crystal_description       block
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.202
_refine_diff_density_min         -0.290
_refine_diff_density_rms         0.059
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     195
_refine_ls_number_reflns         2933
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0784
_refine_ls_R_factor_gt           0.0642
_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^)+(0.0774P)^2^+1.1753P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1686
_refine_ls_wR_factor_ref         0.1769
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2418
_reflns_number_total             2933
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ob01084d2.cif
_cod_data_source_block           8325_2
_cod_database_code               7158788
_shelx_shelxl_version_number     2018/3
_reflns_odcompleteness_completeness 99.90
_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 Ternary CH refined with riding coordinates:
 C11(H11)
2.b Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C7(H7), C8(H8), C10(H10), C15(H15), C16(H16),
 C17(H17), C18(H18), C19(H19)
2.d Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C)
;
_shelx_res_checksum              13474
_shelx_hkl_checksum              24311
_olex2_date_sample_data_collection 2021-11-22
_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 1.704
_oxdiff_exptl_absorpt_empirical_full_min 0.540