Ligand Controlled Ir-Catalyzed Regiodivergent Oxyamination of Unactivated Alkenes.
Lei, Honghui; Conway, Jr, John H; Cook, Caleb C.; Rovis, Tomislav; Journal of the American Chemical Society 141 (2019) 11864–11869; doi:10.1021/jacs.9b06366

data_4128557
_publ_section_title
;
 Ligand Controlled Ir-Catalyzed Regiodivergent Oxyamination of Unactivated
 Alkenes.
;
_journal_issue                   30
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              11864
_journal_page_last               11869
_journal_paper_doi               10.1021/jacs.9b06366
_journal_volume                  141
_journal_year                    2019
_chemical_formula_moiety         'C6 H11 N O2'
_chemical_formula_sum            'C6 H11 N O2'
_chemical_formula_weight         129.16
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2019-04-28
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3510 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 94.519(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   4.57340(17)
_cell_length_b                   9.8222(4)
_cell_length_c                   15.0672(6)
_cell_measurement_reflns_used    2943
_cell_measurement_temperature    100.3(6)
_cell_measurement_theta_max      71.6910
_cell_measurement_theta_min      4.4950
_cell_volume                     674.73(5)
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (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)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.3(6)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0549
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.996
_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     12.00  77.00   1.00    1.00    --   37.78 -99.00 -30.00   65
  2  \w     59.00 108.00   1.00    2.00    --  111.00 -94.00 -90.00   49
  3  \w     63.00 115.00   1.00    2.00    --  111.00-111.00-120.00   52
  4  \w     48.00 125.00   1.00    2.00    --  111.00 -45.00 -60.00   77
  5  \w    101.00 143.00   1.00    2.00    --  111.00 -15.00-150.00   42
  6  \w    112.00 170.00   1.00    2.00    --  111.00  45.00 -60.00   58
  7  \w    139.00 175.00   1.00    2.00    --  111.00  61.00-150.00   36
  8  \w    114.00 140.00   1.00    2.00    --  111.00 111.00 -30.00   26
  9  \w     94.00 123.00   1.00    2.00    --  111.00  61.00-150.00   29
 10  \w     50.00 126.00   1.00    2.00    --  111.00 -45.00-150.00   76
 11  \w     45.00  70.00   1.00    2.00    --  111.00 -77.00-180.00   25
 12  \w     46.00  96.00   1.00    2.00    --  111.00 -64.00-152.99   50
 13  \w     45.00  71.00   1.00    2.00    --  111.00 -15.00-150.00   26
 14  \w     84.00 110.00   1.00    2.00    --  111.00-111.00  30.00   26
 15  \w     85.00 120.00   1.00    2.00    --  111.00 -61.00  60.00   35
 16  \w    119.00 148.00   1.00    2.00    --  111.00 -15.00  30.00   29
 17  \w    129.00 154.00   1.00    2.00    --  111.00  15.00 150.00   25
 18  \w    153.00 178.00   1.00    2.00    --  111.00  61.00  90.00   25
 19  \w    153.00 178.00   1.00    2.00    --  111.00 111.00 120.00   25
 20  \w     74.00 147.00   1.00    2.00    --  111.00 -15.00 120.00   73
 21  \w     77.00 107.00   1.00    2.00    --  111.00 -94.00 150.00   30
 22  \w     65.00 107.00   1.00    2.00    --  111.00 -94.00  30.00   42
 23  \w     41.00  67.00   1.00    2.00    --  111.00-111.00  30.00   26
 24  \w     45.00 105.00   1.00    2.00    --  111.00 -94.00  90.00   60
 25  \w     44.00 122.00   1.00    2.00    --  111.00 -45.00  60.00   78
 26  \w     40.00  89.00   1.00    2.00    --  111.00 -15.00  30.00   49
 27  \w     70.00  98.00   1.00    2.00    --  111.00 178.00 120.00   28
 28  \w    -51.00  30.00   1.00    1.00    --  -37.78  57.00-150.00   81
 29  \w   -105.00 -80.00   1.00    1.00    --  -37.78 -77.00 120.00   25
 30  \w    -62.00 -36.00   1.00    1.00    --  -37.78-178.00-120.00   26
 31  \w    -78.00 -49.00   1.00    1.00    --  -37.78-178.00 -90.00   29
 32  \w   -105.00 -29.00   1.00    1.00    --  -37.78 -57.00  60.00   76
 33  \w    -74.00 -11.00   1.00    1.00    --  -37.78 -77.00 120.00   63
 34  \w   -109.00 -45.00   1.00    1.00    --  -37.78 178.00 150.00   64
 35  \w    105.00 130.00   1.00    2.00    --  111.00 178.00-180.00   25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, EosS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1612853000
_diffrn_orient_matrix_UB_12      0.0955691000
_diffrn_orient_matrix_UB_13      -0.0686248000
_diffrn_orient_matrix_UB_21      0.0992930000
_diffrn_orient_matrix_UB_22      -0.0891176000
_diffrn_orient_matrix_UB_23      -0.0762387000
_diffrn_orient_matrix_UB_31      -0.2797688000
_diffrn_orient_matrix_UB_32      -0.0866621000
_diffrn_orient_matrix_UB_33      0.0027455000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0298
_diffrn_reflns_av_unetI/netI     0.0245
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            5116
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.739
_diffrn_reflns_theta_min         5.381
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.787
_exptl_absorpt_correction_T_max  0.955
_exptl_absorpt_correction_T_min  0.886
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
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    1.271
_exptl_crystal_description       block
_exptl_crystal_F_000             280
_exptl_crystal_size_max          0.271
_exptl_crystal_size_mid          0.118
_exptl_crystal_size_min          0.074
_refine_diff_density_max         0.228
_refine_diff_density_min         -0.192
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     107
_refine_ls_number_reflns         1338
_refine_ls_number_restraints     12
_refine_ls_restrained_S_all      1.089
_refine_ls_R_factor_all          0.0502
_refine_ls_R_factor_gt           0.0478
_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^)+(0.0859P)^2^+0.1801P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1329
_refine_ls_wR_factor_ref         0.1358
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1253
_reflns_number_total             1338
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja9b06366_si_004.cif
_cod_data_source_block           honghui3
_cod_original_cell_volume        674.72(5)
_cod_database_code               4128557
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C6 H11 N O2'
_reflns_odcompleteness_completeness 97.74
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     73.59
_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, All O(H) groups
2. Same fragment restrains
{N1, C2, O3, C4, C5, C6B, C7B, O8B, C9B} sigma for 1-2: 0.02, 1-3: 0.04
as
{N1, C2, O3, C4, C5, C6, C7, O8, C9}
3. Others
 Sof(H5C)=Sof(H5D)=Sof(C6B)=Sof(H6B)=Sof(C7B)=Sof(H7B)=Sof(O8B)=Sof(H8B)=
 Sof(C9B)=Sof(H9B1)=Sof(H9B2)=Sof(H9B3)=1-FVAR(1)
 Sof(H5A)=Sof(H5B)=Sof(C6)=Sof(H6)=Sof(C7)=Sof(H7)=Sof(O8)=Sof(H8)=Sof(C9)=
 Sof(H9A)=Sof(H9B)=Sof(H9C)=FVAR(1)
 Uiso(C6B)=Uiso(C7B)=Uiso(O8B)=Uiso(C9B)=FVAR(2)
4.a Ternary CH refined with riding coordinates:
 C6(H6), C7(H7), C6B(H6B), C7B(H7B)
4.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C5(H5A,H5B), C5(H5C,H5D)
4.c Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C9B(H9B1,H9B2,H9B3)
4.d Idealised tetrahedral OH refined as rotating group:
 O8B(H8B)
;
_shelx_res_checksum              58644
_shelx_hkl_checksum              84685
_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 1.410
_oxdiff_exptl_absorpt_empirical_full_min 0.721