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_7048981
_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         'C28 H24 F N O2'
_chemical_formula_sum            'C28 H24 F N O2'
_chemical_formula_weight         425.48
_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   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2017-12-27
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5375)
;
_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                   5.93196(5)
_cell_length_b                   18.49475(19)
_cell_length_c                   20.30007(19)
_cell_measurement_reflns_used    18874
_cell_measurement_temperature    99.99(10)
_cell_measurement_theta_max      77.2940
_cell_measurement_theta_min      4.3240
_cell_volume                     2227.12(4)
_computing_cell_refinement       'CrysAlisPro 1.171.39.38b (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.38b (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.38b (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_environment      N~2~
_diffrn_ambient_temperature      99.99(10)
_diffrn_detector                 HyPix-6000HE
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 1.000
_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     84.00 177.00   0.50    1.06    --  105.75 137.00  91.00  186
  2  \w     92.00 177.00   0.50    1.06    --  105.75 125.00  60.00  170
  3  \w     33.00  65.00   0.50    1.06    --  105.75 -37.00 120.00   64
  4  \w     33.00  65.00   0.50    1.06    --  105.75 -37.00  90.00   64
  5  \w     34.00 120.00   0.50    1.06    --  105.75 -57.00  60.00  172
  6  \w     34.00 120.00   0.50    1.06    --  105.75 -57.00 -30.00  172
  7  \w    -23.00  60.00   0.50    0.26    --   49.15 -37.00-180.00  166
  8  \w   -121.00 -63.00   0.50    0.26    --  -49.15-137.00  28.00  116
  9  \w   -120.00 -66.00   0.50    0.26    --  -49.15-132.00-154.00  108
 10  \w   -120.00 -35.00   0.50    0.26    --  -49.15 -57.00   0.00  170
 11  \w   -156.00 -62.00   0.50    1.06    --  -84.25 -77.00 -30.00  188
 12  \w   -156.00-100.00   0.50    1.06    --  -84.25 -77.00 120.00  112
 13  \w     35.00 121.00   0.50    0.26    --   49.15  57.00 120.00  172
 14  \w     95.00 178.00   0.50    1.06    --  105.75  37.00  30.00  166
 15  \w     28.00 121.00   0.50    0.26    --   49.15  77.00-150.00  186
 16  \w     95.00 178.00   0.50    1.06    --  105.75  19.00-150.00  166
 17  \w     95.00 178.00   0.50    1.06    --  105.75  19.00 -90.00  166
;
_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      -0.1283734000
_diffrn_orient_matrix_UB_12      -0.0358812000
_diffrn_orient_matrix_UB_13      0.0572662000
_diffrn_orient_matrix_UB_21      -0.2256724000
_diffrn_orient_matrix_UB_22      0.0220690000
_diffrn_orient_matrix_UB_23      -0.0317028000
_diffrn_orient_matrix_UB_31      -0.0050056000
_diffrn_orient_matrix_UB_32      -0.0718877000
_diffrn_orient_matrix_UB_33      -0.0383757000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0337
_diffrn_reflns_av_unetI/netI     0.0221
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            20287
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         67.058
_diffrn_reflns_theta_min         4.356
_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    0.685
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.82423
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.38b (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.269
_exptl_crystal_description       block
_exptl_crystal_F_000             896
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.178
_refine_diff_density_min         -0.133
_refine_diff_density_rms         0.031
_refine_ls_abs_structure_details
;
 Flack x determined using 1630 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.06(4)
_refine_ls_extinction_coef       0.0024(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     298
_refine_ls_number_reflns         3962
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.0244
_refine_ls_R_factor_gt           0.0240
_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^)+(0.0289P)^2^+0.3699P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0603
_refine_ls_wR_factor_ref         0.0605
_reflns_Friedel_coverage         0.717
_reflns_Friedel_fraction_full    0.983
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                3901
_reflns_number_total             3962
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8dt05156a2.cif
_cod_data_source_block           exp_850_harveymudd_2
_cod_depositor_comments
'Adding full bibliography for 7048978--7048982.cif.'
_cod_database_code               7048981
_shelxl_version_number           2014-3
_chemical_oxdiff_formula         'C28 H25 N1 O2 F'
_diffrn_oxdiff_ac3_digest_frames
;
01657f4d68fddf9c0b4992ce2aa17a46b2025449fe8
;
_diffrn_oxdiff_ac3_digest_hkl
;
014d3ab6a371f4dc426d453d6c1861b84c933e
;
_reflns_odcompleteness_completeness 99.87
_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
2.a Ternary CH refined with riding coordinates:
 C2(H2A)
2.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B)
2.c Aromatic/amide H refined with riding coordinates:
 C19(H19), C18(H18), C17(H17), C32(H32), C23(H23), C30(H30), C8(H8), C25(H25),
 C14(H14), C16(H16), C22(H22), C0AA(H0AA), C7(H7), C12(H12), C13(H13), C10(H10),
  C6(H6), C5(H5), C11(H11)
;
_olex2_exptl_crystal_mounting_method
;
150 mu Mitegen loop
;
_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 1.424
_oxdiff_exptl_absorpt_empirical_full_min 0.722