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_7247250
_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         'C20 H22 B P'
_chemical_formula_sum            'C20 H22 B P'
_chemical_formula_weight         304.15
_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             2023-03-09
_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                 95.946(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.76040(10)
_cell_length_b                   16.4043(3)
_cell_length_c                   15.8328(3)
_cell_measurement_reflns_used    7208
_cell_measurement_temperature    180.00(10)
_cell_measurement_theta_max      75.9870
_cell_measurement_theta_min      2.6630
_cell_volume                     1746.41(5)
_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      180.00(10)
_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 0.999
_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    -56.00  26.00   0.50    0.05    --  -46.72  49.00 -63.00  164
  2  \w   -110.00 -31.00   0.50    0.07    --  -95.00  49.00 -63.00  158
  3  \w   -159.00 -87.00   0.50    0.07    --  -95.00 -94.00 -90.00  144
  4  \w   -143.00 -80.00   0.50    0.07    --  -95.00 -49.00 148.00  126
  5  \w   -119.00 -53.00   0.50    0.05    --  -46.72 -49.00 148.00  132
  6  \w     72.00  98.00   0.50    0.05    --   46.72  49.00 -63.00   52
  7  \w     98.00 129.00   0.50    0.07    --  107.00  49.00 -63.00   62
  8  \w    100.00 159.00   0.50    0.07    --  107.00  15.00 -30.00  118
  9  \w     92.00 160.00   0.50    0.07    --  107.00  30.00  30.00  136
 10  \w     91.00 158.00   0.50    0.07    --  107.00  15.00  90.00  134
 11  \w     69.00  95.00   0.50    0.07    --  107.00 -94.00 -30.00   52
 12  \w     75.00 101.00   0.50    0.07    --  107.00 -94.00   0.00   52
 13  \w     36.00  68.00   0.50    0.07    --  107.00 -94.00 -30.00   64
 14  \w     40.00  66.00   0.50    0.07    --  107.00 -94.00   0.00   52
 15  \w     47.00 110.00   0.50    0.07    --  107.00-125.00 150.00  126
 16  \w    -24.00  32.00   0.50    0.05    --   46.72 -49.00 148.00  112
 17  \w     34.00  59.00   0.50    0.07    --  107.00 -49.00 148.00   50
 18  \w     20.00  90.00   0.50    0.05    --   46.72-125.00   0.00  140
;
_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      -0.0936875000
_diffrn_orient_matrix_UB_12      -0.0417087000
_diffrn_orient_matrix_UB_13      -0.0818086000
_diffrn_orient_matrix_UB_21      0.2027739000
_diffrn_orient_matrix_UB_22      -0.0382362000
_diffrn_orient_matrix_UB_23      -0.0129018000
_diffrn_orient_matrix_UB_31      -0.0517441000
_diffrn_orient_matrix_UB_32      -0.0749252000
_diffrn_orient_matrix_UB_33      0.0520113000
_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  0.0636
_diffrn_reflns_av_unetI/netI     0.0538
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            10413
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        66.595
_diffrn_reflns_theta_max         66.595
_diffrn_reflns_theta_min         3.891
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.313
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.48640
_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    1.157
_exptl_crystal_description       block
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.467
_refine_diff_density_min         -0.336
_refine_diff_density_rms         0.072
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     212
_refine_ls_number_reflns         3073
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0582
_refine_ls_R_factor_gt           0.0536
_refine_ls_shift/su_max          0.007
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0981P)^2^+0.5739P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1468
_refine_ls_wR_factor_ref         0.1532
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2732
_reflns_number_total             3073
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3gc02469e2.cif
_cod_data_source_block           20230308-sw-11
_cod_depositor_comments
'Adding full bibliography for 7247250--7247251.cif.'
_cod_original_cell_volume        1746.40(5)
_cod_database_code               7247250
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H P B'
_shelx_estimated_absorpt_t_max   0.891
_shelx_estimated_absorpt_t_min   0.837
_olex2_refinement_description
;
1.a Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B)
1.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C9(H9), C10(H10), C11(H11), C12(H12),
 C13(H13), C16(H16), C18(H18), C19(H19), C20(H20)
1.c Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C)
;
_shelx_res_checksum              91450
_shelx_hkl_checksum              32850
_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 3.121
_oxdiff_exptl_absorpt_empirical_full_min 0.337