Direct Carbon–Carbon σ Bond Amination of Unstrained Arylalkylketones
Hu, Xinwei; Shao, Youxiang; Xie, Haisheng; Chen, Xin; Chen, Fengjuan; Ke, Zhuofeng; Jiang, Huanfeng; Zeng, Wei; ACS Catalysis  (2020) 8402–8408; doi:10.1021/acscatal.0c02683

data_4517857
_publ_section_title
;
 Direct Carbon--Carbon \s Bond Amination of Unstrained Arylalkylketones
;
_journal_name_full               'ACS Catalysis'
_journal_page_first              8402
_journal_page_last               8408
_journal_paper_doi               10.1021/acscatal.0c02683
_journal_year                    2020
_chemical_formula_moiety         'C26 H20 F N3 O2 S'
_chemical_formula_sum            'C26 H20 F N3 O2 S'
_chemical_formula_weight         457.51
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2019-06-21
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 92.357(4)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   19.9143(10)
_cell_length_b                   10.6749(6)
_cell_length_c                   20.1936(9)
_cell_measurement_reflns_used    3852
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      27.4220
_cell_measurement_theta_min      2.9230
_cell_volume                     4289.2(4)
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_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    -17.00  29.00   1.00    2.50    --  -11.59 -99.00 120.00   46
  2  \w     18.00  56.00   1.00    2.50    --   11.74-108.00  11.00   38
  3  \w    -60.00  76.00   1.00    2.50    --   11.74   0.00-150.00  136
;
_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      -0.0303070500
_diffrn_orient_matrix_UB_12      0.0328346500
_diffrn_orient_matrix_UB_13      -0.0075803000
_diffrn_orient_matrix_UB_21      0.0185684000
_diffrn_orient_matrix_UB_22      0.0557454000
_diffrn_orient_matrix_UB_23      -0.0047469000
_diffrn_orient_matrix_UB_31      0.0026596500
_diffrn_orient_matrix_UB_32      -0.0151148500
_diffrn_orient_matrix_UB_33      -0.0340051000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0363
_diffrn_reflns_av_unetI/netI     0.0465
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            10395
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        24.997
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_min         2.047
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.190
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.76847
_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            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.417
_exptl_crystal_description       block
_exptl_crystal_F_000             1904
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.09
_refine_diff_density_max         1.040
_refine_diff_density_min         -0.408
_refine_diff_density_rms         0.062
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     303
_refine_ls_number_reflns         3776
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0614
_refine_ls_R_factor_gt           0.0489
_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^)+(0.0514P)^2^+7.8496P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1163
_refine_ls_wR_factor_ref         0.1254
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3081
_reflns_number_total             3776
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs0c02683_si_003.cif
_cod_data_source_block           hxw-2
_cod_depositor_comments
'Adding full bibliography for 4517857--4517858.cif.'
_cod_database_code               4517857
_shelx_shelxl_version_number     2018/3
_reflns_odcompleteness_completeness 99.96
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C13(H13), C8(H8), C5(H5), C19(H19), C10(H10), C15(H15), C21(H21), C12(H12),
 C6(H6), C7(H7), C16(H16), C17(H17), C25(H25), C24(H24), C11(H11), C18(H18)
2.b Idealised Me refined as rotating group:
 C26(H26A,H26B,H26C)
;
_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 1.298
_oxdiff_exptl_absorpt_empirical_full_min 0.484