Palladium-Catalyzed Oxidative Amination of Homoallylic Alcohols: Sequential Installing Carbonyl and Amino Groups along an Alkyl Chain
Jiang, Huanfeng; Ouyang, Lu; Huang, Jiuzhong; Li, Jianxiao; Qi, Chaorong; Wu, Wanqing; Chem. Commun.  (2017) –; doi:10.1039/C7CC06077G

data_7120602
_publ_section_title
;
 Palladium-Catalyzed Oxidative Amination of Homoallylic Alcohols:
 Sequential Installing Carbonyl and Amino Groups along an Alkyl Chain
;
_journal_name_full               'Chem. Commun.'
_journal_paper_doi               10.1039/C7CC06077G
_journal_year                    2017
_chemical_formula_moiety         'C11 H12 N2 O'
_chemical_formula_sum            'C11 H12 N2 O'
_chemical_formula_weight         188.23
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2017-05-19
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_audit_update_record
;
2017-07-03 deposited with the CCDC.
2017-08-29 downloaded from the CCDC.
;
_cell_angle_alpha                85.248(6)
_cell_angle_beta                 82.608(6)
_cell_angle_gamma                72.427(6)
_cell_formula_units_Z            2
_cell_length_a                   6.2899(4)
_cell_length_b                   7.1826(5)
_cell_length_c                   11.4722(8)
_cell_measurement_reflns_used    1569
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      28.5620
_cell_measurement_theta_min      4.5780
_cell_volume                     489.46(6)
_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 0.827
_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     40.00  67.00   1.00    2.80    --   11.74  37.00 -30.00   27
  2  \w     -1.00  81.00   1.00    2.80    --   11.74  57.00 -90.00   82
  3  \w    -43.00 -16.00   1.00    2.80    --   11.74 -57.00  60.00   27
  4  \w    -57.00  34.00   1.00    2.80    --   11.74 -57.00   0.00   91
  5  \w    -14.00  82.00   1.00    2.80    --   11.74  57.00 150.00   96
;
_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      -0.0872307000
_diffrn_orient_matrix_UB_12      0.0584908000
_diffrn_orient_matrix_UB_13      -0.0323992000
_diffrn_orient_matrix_UB_21      -0.0768272000
_diffrn_orient_matrix_UB_22      0.0091580000
_diffrn_orient_matrix_UB_23      0.0516970000
_diffrn_orient_matrix_UB_31      0.0254761000
_diffrn_orient_matrix_UB_32      0.0851381000
_diffrn_orient_matrix_UB_33      0.0131596000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0202
_diffrn_reflns_av_unetI/netI     0.0439
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.827
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            4215
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.827
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.539
_diffrn_reflns_theta_min         3.404
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.95262
_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            orange
_exptl_crystal_density_diffrn    1.277
_exptl_crystal_description       block
_exptl_crystal_F_000             200
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.309
_refine_diff_density_min         -0.236
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     128
_refine_ls_number_reflns         2259
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0674
_refine_ls_R_factor_gt           0.0502
_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^)+(0.0524P)^2^+0.1460P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1164
_refine_ls_wR_factor_ref         0.1294
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1736
_reflns_number_total             2259
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7cc06077g2.cif
_cod_data_source_block           exp_559
_cod_database_code               7120602
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.991
_shelx_estimated_absorpt_t_min   0.985
_reflns_odcompleteness_completeness 99.85
_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.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C8(H8A,H8B)
2.b Aromatic/amide H refined with riding coordinates:
 N2(H2), C2(H2A), C6(H6), C3(H3), C5(H5)
2.c Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C)
;
_olex2_date_sample_data_collection 2017-05-19
_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 1.221
_oxdiff_exptl_absorpt_empirical_full_min 0.658