Catalytic intramolecular hydroamination of aminoallenes using titanium complexes of chiral, tridentate, dianionic imine-diol ligands.
Sha, Fanrui; Mitchell, Benjamin S.; Ye, Christopher Z.; Abelson, Chase S.; Reinheimer, Eric W.; LeMagueres, Pierre; Ferrara, Joseph D.; Takase, Michael K.; Johnson, Adam R.; Dalton transactions (Cambridge, England : 2003) 48 (2019) 9603–9616; doi:10.1039/c8dt05156a

data_7048979
_publ_section_title
;
 Catalytic intramolecular hydroamination of aminoallenes using titanium
 complexes of chiral, tridentate, dianionic imine-diol ligands.
;
_journal_issue                   26
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              9603
_journal_page_last               9616
_journal_paper_doi               10.1039/c8dt05156a
_journal_volume                  48
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C18 H21 N O2'
_chemical_formula_sum            'C18 H21 N O2'
_chemical_formula_weight         283.36
_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'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     dual
_audit_creation_date             2017-11-13
_audit_creation_method
;
Olex2 1.2-ac3
(compiled 2017.03.02 svn.r3394 for Rigaku Oxford Diffraction, GUI svn.r5318)
;
_audit_update_record
;
2018-08-28 deposited with the CCDC.
2019-02-12 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.27660(10)
_cell_length_b                   13.5578(2)
_cell_length_c                   17.4247(2)
_cell_measurement_reflns_used    12871
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      77.1500
_cell_measurement_theta_min      4.0720
_cell_volume                     1482.79(4)
_computing_cell_refinement       'CrysAlisPro 1.171.39.33b (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.33b (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.33b (Rigaku OD, 2017)'
_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_temperature      100(2)
_diffrn_detector                 HyPix-6000HE
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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     98.00 178.00   0.50    0.20    --  105.75  37.00-120.00  160
  2  \w    -56.00  24.00   0.50    0.10    --  -48.91  37.00-120.00  160
  3  \w    -58.00 -11.00   0.50    0.20    --  -84.25  19.00-180.00   94
  4  \w    -58.00 -11.00   0.50    0.20    --  -84.25  19.00-120.00   94
  5  \w   -120.00 -41.00   0.50    0.10    --  -48.91 -37.00 -30.00  158
  6  \w   -155.00-102.00   0.50    0.20    --  -84.25 -57.00-180.00  106
  7  \w     33.00  65.00   0.50    0.20    --  105.75 -37.00-120.00   64
  8  \w     33.00  65.00   0.50    0.20    --  105.75 -37.00-150.00   64
  9  \w     33.00  65.00   0.50    0.20    --  105.75 -37.00 -90.00   64
 10  \w     35.00 119.00   0.50    0.20    --  105.75 -57.00-150.00  168
 11  \w     33.00  65.00   0.50    0.20    --  105.75 -37.00 -60.00   64
 12  \w     33.00  65.00   0.50    0.20    --  105.75 -37.00-180.00   64
 13  \w     33.00  65.00   0.50    0.20    --  105.75 -37.00   0.00   64
 14  \w     33.00  65.00   0.50    0.20    --  105.75 -37.00  30.00   64
 15  \w     33.00  65.00   0.50    0.20    --  105.75 -37.00 120.00   64
 16  \w     33.00  65.00   0.50    0.20    --  105.75 -37.00 150.00   64
 17  \w   -120.00 -28.00   0.50    0.10    --  -48.91 -77.00 150.00  184
 18  \w   -120.00 -36.00   0.50    0.10    --  -48.91 -57.00  60.00  168
 19  \w   -120.00 -36.00   0.50    0.10    --  -48.91 -57.00 -60.00  168
 20  \w   -120.00 -26.00   0.50    0.10    --  -48.91 -82.00-136.00  188
 21  \w     34.00 110.00   0.50    0.20    --  105.75 -99.00-120.00  152
 22  \w     31.00  94.00   0.50    0.10    --   48.91-125.00  60.00  126
 23  \w     34.00 110.00   0.50    0.20    --  105.75 -99.00 120.00  152
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0517900000
_diffrn_orient_matrix_UB_12      0.0410948000
_diffrn_orient_matrix_UB_13      0.0802696000
_diffrn_orient_matrix_UB_21      0.2064903000
_diffrn_orient_matrix_UB_22      -0.0459822000
_diffrn_orient_matrix_UB_23      0.0315297000
_diffrn_orient_matrix_UB_31      0.1220684000
_diffrn_orient_matrix_UB_32      0.0955295000
_diffrn_orient_matrix_UB_33      -0.0192874000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0283
_diffrn_reflns_av_unetI/netI     0.0177
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            13819
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        66.550
_diffrn_reflns_theta_max         66.550
_diffrn_reflns_theta_min         6.038
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.651
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.350
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.33b (Rigaku Oxford Diffraction, 2017)
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    1.269
_exptl_crystal_description       block
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.353
_exptl_crystal_size_mid          0.289
_exptl_crystal_size_min          0.144
_refine_diff_density_max         0.147
_refine_diff_density_min         -0.138
_refine_diff_density_rms         0.032
_refine_ls_abs_structure_details
;
 Flack x determined using 1066 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.03(7)
_refine_ls_extinction_coef       0.0030(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   0.903
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     275
_refine_ls_number_reflns         2621
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.903
_refine_ls_R_factor_all          0.0231
_refine_ls_R_factor_gt           0.0229
_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^)+(0.0362P)^2^+0.3856P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0585
_refine_ls_wR_factor_ref         0.0587
_reflns_Friedel_coverage         0.704
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                2596
_reflns_number_total             2621
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8dt05156a2.cif
_cod_data_source_block           hm_1
_cod_depositor_comments
'Adding full bibliography for 7048978--7048982.cif.'
_cod_database_code               7048979
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         'C18 H21 N O2'
_diffrn_oxdiff_ac3_digest_frames
;
0117adae6b3b44044f9b9e5b36e9a2eb7c02654131b
;
_diffrn_oxdiff_ac3_digest_hkl
;
01248de56741bfee58a3b66911521ceb3e0980
;
_reflns_odcompleteness_completeness 99.87
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
;
_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 1.501
_oxdiff_exptl_absorpt_empirical_full_min 0.842