Organic Photoredox Catalytic α-C(sp3)–H Phosphorylation of Saturated Aza-Heterocycles
Yi, Ming-Jun; Xiao, Teng-Fei; Li, Wen-Hui; Zhang, Yi-Fan; Yan, Pen-Ji; Zhang, Baoxin; Xu, Peng-Fei; Xu, Guo-Qiang; Chemical Communications  (2021) –; doi:10.1039/D1CC05767G

data_7129264
_publ_section_title
;
 Organic Photoredox Catalytic \a-C(sp3)--H Phosphorylation of Saturated
 Aza-Heterocycles
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D1CC05767G
_journal_year                    2021
_chemical_formula_moiety         'C23 H21 F3 N O P'
_chemical_formula_sum            'C23 H21 F3 N O P'
_chemical_formula_weight         415.38
_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             2021-07-02
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6032)
;
_audit_update_record
;
2021-09-29 deposited with the CCDC.	2021-11-15 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 103.0740(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.80270(10)
_cell_length_b                   20.2100(2)
_cell_length_c                   11.48090(10)
_cell_measurement_reflns_used    9770
_cell_measurement_temperature    149.99(10)
_cell_measurement_theta_max      76.1570
_cell_measurement_theta_min      4.5120
_cell_volume                     1989.54(4)
_computing_cell_refinement       'CrysAlisPro 1.171.41.105a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.105a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.105a (Rigaku OD, 2021)'
_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 2014/5 (Sheldrick, 2014)'
_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 0.997
_diffrn_measured_fraction_theta_max 0.950
_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     70.00 118.00   0.50    0.05    --   46.32  55.00  65.00   96
  2  \w    149.00 174.00   0.50    0.05    --  104.25  61.00 -30.00   50
  3  \w     92.00 175.00   0.50    0.05    --  104.25  45.00   0.00  166
  4  \w     93.00 118.00   0.50    0.05    --  104.25  61.00 -30.00   50
  5  \w     97.00 154.00   0.50    0.05    --  104.25  55.00  65.00  114
  6  \w    121.00 147.00   0.50    0.05    --  104.25 125.00 120.00   52
  7  \w     84.00 117.00   0.50    0.05    --  104.25 125.00 120.00   66
  8  \w     50.00 101.00   0.50    0.05    --  104.25 -77.00-180.00  102
  9  \w     37.00  64.00   0.50    0.05    --  104.25 -61.00-180.00   54
 10  \w     46.00  72.00   0.50    0.05    --  104.25 -61.00-120.00   52
 11  \w     32.00  64.00   0.50    0.05    --  104.25 -55.00 -78.00   64
 12  \w    -25.00  61.00   0.50    0.05    --   46.32 -55.00 -78.00  172
 13  \w    -49.00  26.00   0.50    0.05    --  -46.32  55.00  65.00  150
 14  \w    -64.00 -29.00   0.50    0.05    -- -102.00  61.00 120.00   70
 15  \w    -69.00 -29.00   0.50    0.05    -- -102.00  61.00 -60.00   80
 16  \w    -66.00 -31.00   0.50    0.05    -- -102.00  61.00-180.00   70
 17  \w    -69.00 -29.00   0.50    0.05    -- -102.00  61.00-150.00   80
 18  \w    -67.00 -35.00   0.50    0.05    -- -102.00  61.00 -90.00   64
 19  \w    -59.00 -30.00   0.50    0.05    -- -102.00  55.00  65.00   58
 20  \w   -119.00 -75.00   0.50    0.05    --  -46.32 -55.00 -78.00   88
 21  \w   -174.00-145.00   0.50    0.05    -- -102.00 -55.00 -78.00   58
 22  \w   -173.00-133.00   0.50    0.05    -- -102.00 -45.00   0.00   80
 23  \w   -115.00 -90.00   0.50    0.05    -- -102.00 -45.00   0.00   50
 24  \w   -118.00 -75.00   0.50    0.05    --  -46.32-125.00  30.00   86
 25  \w   -111.00 -74.00   0.50    0.05    --  -46.32-125.00  60.00   74
;
_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      0.1166156000
_diffrn_orient_matrix_UB_12      0.0499475000
_diffrn_orient_matrix_UB_13      0.0721094000
_diffrn_orient_matrix_UB_21      -0.0811723000
_diffrn_orient_matrix_UB_22      -0.0058269000
_diffrn_orient_matrix_UB_23      0.1051567000
_diffrn_orient_matrix_UB_31      0.1099063000
_diffrn_orient_matrix_UB_32      -0.0573278000
_diffrn_orient_matrix_UB_33      0.0520739000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0299
_diffrn_reflns_av_unetI/netI     0.0271
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.950
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            13733
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.950
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.137
_diffrn_reflns_theta_min         4.375
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.595
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.71833
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.105a (Rigaku Oxford Diffraction, 2021)
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    1.387
_exptl_crystal_description       block
_exptl_crystal_F_000             864
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.387
_refine_diff_density_min         -0.342
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     289
_refine_ls_number_reflns         3952
_refine_ls_number_restraints     42
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.0408
_refine_ls_R_factor_gt           0.0377
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0495P)^2^+0.8027P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0985
_refine_ls_wR_factor_ref         0.1012
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3591
_reflns_number_total             3952
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1cc05767g2.cif
_cod_data_source_block           yimingj_0702_auto
_cod_database_code               7129264
_shelx_shelxl_version_number     2018/1
_reflns_odcompleteness_completeness 99.86
_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. Uiso/Uaniso restraints and constraints
Uanis(F1) \\sim Ueq, Uanis(F00T) \\sim Ueq, Uanis(F3) \\sim Ueq, Uanis(F00K)
\\sim Ueq, Uanis(C8) \\sim Ueq, Uanis(F4) \\sim Ueq, Uanis(F00I) \\sim Ueq:
with sigma of 0.01 and sigma for terminal atoms of 0.02
3. Others
 Fixed Sof: F00I(0.5) F00K(0.5) F00T(0.5) F1(0.5) F3(0.5) F4(0.5)
4.a Ternary CH refined with riding coordinates:
 C1(H1)
4.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B)
4.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C007(H007), C9(H9), C12(H12), C13(H13), C14(H14), C15(H15),
 C16(H16), C18(H18), C19(H19), C20(H20), C21(H21), C22(H22)
;
_shelx_res_checksum              35862
_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 1.472
_oxdiff_exptl_absorpt_empirical_full_min 0.654