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_4128558
_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 H10 Br N O'
_chemical_formula_sum            'C6 H10 Br N O'
_chemical_formula_weight         192.06
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2019-05-01
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3510 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                70.172(6)
_cell_angle_beta                 89.251(6)
_cell_angle_gamma                79.122(7)
_cell_formula_units_Z            2
_cell_length_a                   5.9616(5)
_cell_length_b                   7.0596(5)
_cell_length_c                   9.5102(6)
_cell_measurement_reflns_used    1522
_cell_measurement_temperature    99.98(11)
_cell_measurement_theta_max      28.1490
_cell_measurement_theta_min      4.5580
_cell_volume                     369.19(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-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.98(11)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0549
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.809
_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    -39.00   4.00   1.00    2.00    --  -14.01  77.00 120.00   43
  2  \w     25.00  52.00   1.00    2.00    --  -14.01  77.00 150.00   27
  3  \w     19.00  81.00   1.00    2.00    --   16.51  77.00 150.00   62
  4  \w     -9.00  82.00   1.00    2.00    --   16.51  77.00  60.00   91
  5  \w     35.00  83.00   1.00    2.00    --   16.51  77.00 -60.00   48
  6  \w     -8.00  72.00   1.00    2.00    --   16.51  77.00 -90.00   80
;
_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      -0.0260852000
_diffrn_orient_matrix_UB_12      0.0741875000
_diffrn_orient_matrix_UB_13      -0.0727180000
_diffrn_orient_matrix_UB_21      -0.0624858000
_diffrn_orient_matrix_UB_22      0.0705021000
_diffrn_orient_matrix_UB_23      0.0313429000
_diffrn_orient_matrix_UB_31      0.1006891000
_diffrn_orient_matrix_UB_32      0.0372583000
_diffrn_orient_matrix_UB_33      0.0058885000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0347
_diffrn_reflns_av_unetI/netI     0.0655
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.809
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            2644
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.809
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.346
_diffrn_reflns_theta_min         4.060
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    5.486
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.128
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.46 (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            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.728
_exptl_crystal_description       block
_exptl_crystal_F_000             192
_exptl_crystal_size_max          0.562
_exptl_crystal_size_mid          0.237
_exptl_crystal_size_min          0.179
_refine_diff_density_max         0.539
_refine_diff_density_min         -0.569
_refine_diff_density_rms         0.105
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.993
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     125
_refine_ls_number_reflns         1649
_refine_ls_number_restraints     77
_refine_ls_restrained_S_all      0.977
_refine_ls_R_factor_all          0.0390
_refine_ls_R_factor_gt           0.0323
_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^)+(0.0171P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0605
_refine_ls_wR_factor_ref         0.0647
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1470
_reflns_number_total             1649
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja9b06366_si_002.cif
_cod_data_source_block           honghui4
_cod_database_code               4128558
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C6 H10 Br N O'
_reflns_odcompleteness_completeness 98.67
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained atomic chiral volume
 C2
 fixed at 0 with sigma of 0.1
 C2B
 fixed at 0 with sigma of 0.1
3. Uiso/Uaniso restraints and constraints
All non-hydrogen atoms have similar U: within 1A with sigma of 0.01 and sigma
for terminal atoms of 0.02
4. Same fragment restrains
{N1B, C2B, O3B, C4B, C5B, C6B, C7B, Br8B, C9B} sigma for 1-2: 0.02, 1-3: 0.04
as
{N1, C2, O3, C4, C5, C6, C7, Br8, C9}
5. Others
 Sof(N1B)=Sof(H1B)=Sof(C2B)=Sof(O3B)=Sof(C4B)=Sof(H4B1)=Sof(H4B2)=Sof(C5B)=
 Sof(H5B1)=Sof(H5B2)=Sof(C6B)=Sof(H6B)=Sof(C7B)=Sof(H7B)=Sof(Br8B)=Sof(C9B)=
 Sof(H9B1)=Sof(H9B2)=Sof(H9B3)=Sof(Q1)=Sof(Q2)=Sof(Q3)=Sof(Q4)=Sof(Q5)=Sof(Q6)=
 Sof(Q7)=Sof(Q8)=Sof(Q9)=Sof(Q10)=Sof(Q11)=Sof(Q12)=Sof(Q13)=Sof(Q14)=Sof(Q15)=
 Sof(Q16)=Sof(Q17)=Sof(Q18)=Sof(Q19)=Sof(Q20)=1-FVAR(1)
 Sof(N1)=Sof(H1)=Sof(C2)=Sof(O3)=Sof(C4)=Sof(H4A)=Sof(H4B)=Sof(C5)=Sof(H5A)=
 Sof(H5B)=Sof(C6)=Sof(H6)=Sof(C7)=Sof(H7)=Sof(Br8)=Sof(C9)=Sof(H9A)=Sof(H9B)=
 Sof(H9C)=FVAR(1)
6.a Ternary CH refined with riding coordinates:
 C6(H6), C7(H7), C6B(H6B), C7B(H7B)
6.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C5(H5A,H5B), C4B(H4B1,H4B2), C5B(H5B1,H5B2)
6.c Aromatic/amide H refined with riding coordinates:
 N1B(H1B)
6.d Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C9B(H9B1,H9B2,H9B3)
;
_shelx_res_checksum              15372
_shelx_hkl_checksum              6328
_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 1.159
_oxdiff_exptl_absorpt_empirical_full_min 0.877