Organic Photoredox Catalytic Amino-heteroarylation of Unactivated Olefins to Access Distal Amino Ketones
Zhang, Ji-Hua; Xiao, Teng-Fei; Ji, Zi-Qin; Chen, Han-Nan; Yan, Pen-Ji; Luo, Yong-Chun; Xu, Peng-Fei; Xu, Guo-Qiang; Chemical Communications  (2022) –; doi:10.1039/D1CC07189K

data_7129636
_publ_section_title
;
 Organic Photoredox Catalytic Amino-heteroarylation of Unactivated Olefins
 to Access Distal Amino Ketones
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D1CC07189K
_journal_year                    2022
_chemical_formula_moiety         'C26 H26 N1.95 O4 S2.05'
_chemical_formula_sum            'C26 H26 N1.95 O4 S2.05'
_chemical_formula_weight         495.51
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-10-25
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6403)
;
_audit_update_record
;
2021-11-10 deposited with the CCDC.	2022-01-28 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 96.606(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.8319(3)
_cell_length_b                   11.5048(3)
_cell_length_c                   21.1845(6)
_cell_measurement_reflns_used    12235
_cell_measurement_temperature    149.99(10)
_cell_measurement_theta_max      30.5590
_cell_measurement_theta_min      1.9990
_cell_volume                     2380.35(12)
_computing_cell_refinement       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      149.99(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.821
_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     -8.00  76.00   0.50    1.00    --    3.62  37.00  30.00  168
  2  \w    -14.00  11.00   0.50    1.00    --    3.62  84.00 -14.00   50
  3  \w    -18.00  36.00   0.50    1.00    --    3.62 -99.00 -60.00  108
  4  \w    -34.00  11.00   0.50    1.00    --    3.62 -84.00-134.00   90
  5  \w     -5.00  31.00   0.50    1.00    --    3.62 -99.00-180.00   72
  6  \w    -69.00 -22.50   0.50    1.00    --    3.62 -37.00  90.00   93
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0702859000
_diffrn_orient_matrix_UB_12      -0.0149818000
_diffrn_orient_matrix_UB_13      -0.0060551000
_diffrn_orient_matrix_UB_21      -0.0178292000
_diffrn_orient_matrix_UB_22      0.0521937000
_diffrn_orient_matrix_UB_23      0.0148241000
_diffrn_orient_matrix_UB_31      -0.0040409000
_diffrn_orient_matrix_UB_32      0.0292188000
_diffrn_orient_matrix_UB_33      -0.0296517000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0352
_diffrn_reflns_av_unetI/netI     0.0323
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.821
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            23904
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.821
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.648
_diffrn_reflns_theta_min         1.935
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.265
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.62516
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.383
_exptl_crystal_description       block
_exptl_crystal_F_000             1042
_exptl_crystal_size_max          0.07
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.638
_refine_diff_density_min         -0.638
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     327
_refine_ls_number_reflns         6031
_refine_ls_number_restraints     26
_refine_ls_restrained_S_all      1.140
_refine_ls_R_factor_all          0.0632
_refine_ls_R_factor_gt           0.0486
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0589P)^2^+1.2559P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1229
_refine_ls_wR_factor_ref         0.1309
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4789
_reflns_number_total             6031
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1cc07189k2.cif
_cod_data_source_block           zhangjih_1022
_cod_original_cell_volume        2380.36(12)
_cod_database_code               7129636
_shelx_shelxl_version_number     2018/1
_reflns_odcompleteness_completeness 99.94
_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 distances
 C20-S3 \\sim C20-N3
 with sigma of 0.02
 C7-S3 \\sim C7-N3
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(S2) \\sim Ueq, Uanis(N2) \\sim Ueq, Uanis(N3) \\sim Ueq, Uanis(S3) \\sim
Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(N3) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.005
4. Others
 Fixed Sof: S2(0.25) S3(0.8) N2(0.75) N3(0.2)
5.a Ternary CH refined with riding coordinates:
 C8(H8)
5.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C13(H13A,H13B), C18(H18A,H18B)
5.c Aromatic/amide H refined with riding coordinates:
 N1(H1), C2(H2), C3(H3), C5(H5), C9(H9), C12(H12), C14(H14), C17(H17),
 C19(H19), C21(H21), C22(H22), C23(H23), C24(H24)
5.d Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C25(H25A,H25B,H25C)
;
_shelx_res_checksum              91326
_shelx_hkl_checksum              15344
_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 1.251
_oxdiff_exptl_absorpt_empirical_full_min 0.572