Photoinduced cobaloxime catalysis enabled dehydrogenative C2-phosphinylation of bicyclo[1.1.0]butanes to access phosphorylated cyclobutenes
Chang, Yunong; Bian, Fangyu; Guo, Jiefei; Li, Miao-Miao; Ding, Wei; RSC Advances 15 (2025) 24053–24057; doi:10.1039/D5RA03697F

data_7250678
_publ_section_title
;
 Photoinduced cobaloxime catalysis enabled dehydrogenative
 C2-phosphinylation of bicyclo[1.1.0]butanes to access phosphorylated
 cyclobutenes
;
_journal_issue                   29
_journal_name_full               'RSC Advances'
_journal_page_first              24053
_journal_page_last               24057
_journal_paper_doi               10.1039/D5RA03697F
_journal_volume                  15
_journal_year                    2025
_chemical_formula_moiety         'C24 H22 N O2 P'
_chemical_formula_sum            'C24 H22 N O2 P'
_chemical_formula_weight         387.39
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2024-06-17
_audit_creation_method
;
Olex2 1.5-beta
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6439)
;
_audit_update_record
;
2025-02-11 deposited with the CCDC.	2025-07-04 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 102.1150(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.53630(10)
_cell_length_b                   12.06750(10)
_cell_length_c                   14.55360(10)
_cell_measurement_reflns_used    10423
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      73.0330
_cell_measurement_theta_min      4.4570
_cell_volume                     1980.95(3)
_computing_cell_refinement       'CrysAlisPro 1.171.43.92a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.43.92a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.43.92a (Rigaku OD, 2023)'
_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      100.00(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 0.974
_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   -111.00 -42.00   0.50    0.10    --  -99.00 125.00   0.00  138
  2  \w   -106.00 -59.00   0.50    0.10    --  -99.00 106.00 -89.98   94
  3  \w    -23.00  29.00   0.50    0.05    --  -45.87  19.00-120.00  104
  4  \w     -8.00  17.00   0.50    0.05    --  -45.87   4.00-154.00   50
  5  \w   -102.00   4.00   0.50    0.05    --  -45.87  -4.00  25.00  212
  6  \w     43.00 145.00   0.50    0.10    --   99.00   4.00-154.00  204
  7  \w     38.00  75.00   0.50    0.05    --   45.87   4.00-154.00   74
  8  \w   -163.00 -46.00   0.50    0.10    --  -99.00  -4.00  25.00  234
  9  \w    -15.00  10.00   0.50    0.05    --   45.87  -4.00  25.00   50
 10  \w     28.00  71.00   0.50    0.10    --   99.00 -61.00 -90.00   86
 11  \w     27.00  52.00   0.50    0.10    --   99.00 -45.00-150.00   50
 12  \w     31.00  73.00   0.50    0.10    --   99.00 -61.00-180.00   84
 13  \w     39.00  72.00   0.50    0.10    --   99.00 -61.00 -60.00   66
 14  \w     28.00  72.00   0.50    0.10    --   99.00 -61.00 -30.00   88
 15  \w     36.00  86.00   0.50    0.10    --   99.00 -94.00 -90.00  100
 16  \w     80.00 112.00   0.50    0.10    --   99.00-125.00-150.00   64
 17  \w     41.00  92.00   0.50    0.05    --   45.87-125.00 -60.00  102
 18  \w     62.00 110.00   0.50    0.10    --   99.00-125.00  30.00   96
 19  \w     48.00  94.00   0.50    0.10    --   99.00 -94.00  90.00   92
;
_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      -0.1221757000
_diffrn_orient_matrix_UB_12      -0.0028745000
_diffrn_orient_matrix_UB_13      -0.0676932000
_diffrn_orient_matrix_UB_21      0.0608984000
_diffrn_orient_matrix_UB_22      0.0059435000
_diffrn_orient_matrix_UB_23      -0.0845363000
_diffrn_orient_matrix_UB_31      0.0058338000
_diffrn_orient_matrix_UB_32      -0.1273734000
_diffrn_orient_matrix_UB_33      -0.0023877000
_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  0.0264
_diffrn_reflns_av_unetI/netI     0.0236
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            13272
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.237
_diffrn_reflns_theta_min         4.462
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.380
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.69864
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.43.92a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.299
_exptl_crystal_description       block
_exptl_crystal_F_000             816
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.413
_refine_diff_density_min         -0.340
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       0.0021(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     255
_refine_ls_number_reflns         3870
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0351
_refine_ls_R_factor_gt           0.0330
_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^)+(0.0443P)^2^+0.8992P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0857
_refine_ls_wR_factor_ref         0.0874
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3623
_reflns_number_total             3870
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ra03697f2.cif
_cod_data_source_block           cyn-1-68
_cod_original_cell_volume        1980.94(3)
_cod_database_code               7250678
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H O N P'
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C13(H13)
2.b Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C8(H8), C9(H9), C10(H10), C11(H11),
 C12(H12), C15(H15), C20(H20), C21(H21), C22(H22), C23(H23), C24(H24)
2.d Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C)
;
_shelx_res_checksum              69863
_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 1.479
_oxdiff_exptl_absorpt_empirical_full_min 0.586