Photoinduced ligand-to-iron charge transfer enabled C(sp3)–H phosphorylation of hydrocarbons
Shi, Wei; Zhong, Ping-Fu; Qi, Xu-Kuan; Yang, Chao; Guo, Lin; Xia, Wujiong; Green Chemistry 25 (2023) 7817–7824; doi:10.1039/D3GC02469E

data_7247251
_publ_section_title
;
 Photoinduced ligand-to-iron charge transfer enabled C(sp3)--H
 phosphorylation of hydrocarbons
;
_journal_issue                   19
_journal_name_full               'Green Chemistry'
_journal_page_first              7817
_journal_page_last               7824
_journal_paper_doi               10.1039/D3GC02469E
_journal_volume                  25
_journal_year                    2023
_chemical_formula_moiety         'C19 H24 B P'
_chemical_formula_sum            'C19 H24 B P'
_chemical_formula_weight         294.16
_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   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2023-06-09
_audit_creation_method
;
Olex2 1.5-beta
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6439)
;
_audit_update_record
;
2023-06-13 deposited with the CCDC.	2023-08-25 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 101.613(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.60160(10)
_cell_length_b                   17.7257(4)
_cell_length_c                   14.5686(3)
_cell_measurement_reflns_used    8047
_cell_measurement_temperature    180.3(7)
_cell_measurement_theta_max      76.2170
_cell_measurement_theta_min      2.4520
_cell_volume                     1669.89(6)
_computing_cell_refinement       'CrysAlisPro 1.171.42.67a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.67a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.67a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      180.3(7)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.927
_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     35.00  60.00   0.50    0.05    --   46.97-121.00 117.00   50
  2  \w     77.00 110.00   0.50    0.10    --  107.00-121.00 117.00   66
  3  \w     71.00  96.00   0.50    0.05    --   46.97-151.00 -43.00   50
  4  \w     43.00 106.00   0.50    0.10    --  107.00 -94.00-120.00  126
  5  \w    102.00 128.00   0.50    0.10    --  107.00-151.00 -43.00   52
  6  \w     35.00 102.00   0.50    0.10    --  107.00 -94.00 120.00  134
  7  \w   -119.00 -32.00   0.50    0.05    --  -46.97 -57.00  30.00  174
  8  \w   -112.00 -87.00   0.50    0.05    --  -46.97-151.00 -43.00   50
  9  \w   -137.00 -88.00   0.50    0.10    --  -95.00-121.00 117.00   98
 10  \w   -113.00 -71.00   0.50    0.10    --  -95.00  15.00  90.00   84
 11  \w    -64.00 -20.00   0.50    0.10    --  -95.00  15.00  90.00   88
 12  \w   -111.00 -24.00   0.50    0.10    --  -95.00  61.00  30.00  174
 13  \w   -127.00 -28.00   0.50    0.10    --  -95.00 151.00   0.00  198
 14  \w   -110.00 -21.00   0.50    0.10    --  -95.00  30.00-120.00  178
 15  \w     95.00 143.00   0.50    0.10    --  107.00  30.00 -60.00   96
 16  \w     71.00 118.00   0.50    0.05    --   46.97 151.00   0.00   94
 17  \w    112.00 138.00   0.50    0.10    --  107.00 151.00   0.00   52
 18  \w     86.00 117.00   0.50    0.05    --   46.97  57.00  60.00   62
 19  \w     32.00  71.00   0.50    0.05    --   46.97  57.00  60.00   78
;
_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      0.0881548000
_diffrn_orient_matrix_UB_12      -0.0805340000
_diffrn_orient_matrix_UB_13      0.0002350000
_diffrn_orient_matrix_UB_21      0.2206893000
_diffrn_orient_matrix_UB_22      0.0315110000
_diffrn_orient_matrix_UB_23      0.0306578000
_diffrn_orient_matrix_UB_31      -0.0157060000
_diffrn_orient_matrix_UB_32      -0.0091290000
_diffrn_orient_matrix_UB_33      0.1034729000
_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  0.0352
_diffrn_reflns_av_unetI/netI     0.0319
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.927
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            11292
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.927
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.508
_diffrn_reflns_theta_min         3.977
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.352
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.52965
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.67a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.170
_exptl_crystal_description       block
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.975
_refine_diff_density_min         -0.383
_refine_diff_density_rms         0.069
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     202
_refine_ls_number_reflns         3261
_refine_ls_number_restraints     7
_refine_ls_restrained_S_all      1.094
_refine_ls_R_factor_all          0.0677
_refine_ls_R_factor_gt           0.0625
_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^)+(0.0790P)^2^+2.1350P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1659
_refine_ls_wR_factor_ref         0.1725
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3056
_reflns_number_total             3261
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3gc02469e2.cif
_cod_data_source_block           20230510-sw-13
_cod_depositor_comments
'Adding full bibliography for 7247250--7247251.cif.'
_cod_database_code               7247251
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H P B'
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Rigid bond restraints
 C1, C6
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
3. Uiso/Uaniso restraints and constraints
C6 \\sim C1: within 2A with sigma of 0.002 and sigma for terminal atoms of
0.004 within 2A
4.a Ternary CH refined with riding coordinates:
 C1(H1), C3(H3), C6(H6)
4.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C4(H4A,H4B), C5(H5A,H5B), C7(H7A,H7B)
4.c Aromatic/amide H refined with riding coordinates:
 C9(H9), C10(H10), C11(H11), C12(H12), C13(H13), C16(H16), C17(H17), C18(H18),
 C19(H19), C20(H20)
;
_shelx_res_checksum              79089
_shelx_hkl_checksum              33402
_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 2.181
_oxdiff_exptl_absorpt_empirical_full_min 0.486