Phosphination of aryl/alkyl bromides <i>via</i> Mn-mediated reductive C-P coupling.
Dong, Likun; Zhong, Bing; Zhang, Yu-Shan; Yang, Jin-Dong; Cheng, Jin-Pei; Chemical communications (Cambridge, England) 60 (2024) 12549–12552; doi:10.1039/d4cc04750h

data_7133791
_publ_section_title
;
 Phosphination of aryl/alkyl bromides <i>via</i> Mn-mediated reductive C-P
 coupling.
;
_journal_issue                   86
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              12549
_journal_page_last               12552
_journal_paper_doi               10.1039/d4cc04750h
_journal_volume                  60
_journal_year                    2024
_chemical_formula_moiety         'C13.967 H19 N2 O P'
_chemical_formula_sum            'C13.967 H19 N2 O P'
_chemical_formula_weight         261.903
_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'
_symmetry_Int_Tables_number      14
_atom_sites_solution_primary     iterative
_audit_block_doi                 10.5517/ccdc.csd.cc2l0l6f
_audit_creation_date             2024-09-12
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2024-09-13 deposited with the CCDC.	2024-10-01 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 97.9891(15)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.23898(13)
_cell_length_b                   10.49700(16)
_cell_length_c                   18.2476(3)
_cell_measurement_reflns_used    6531
_cell_measurement_temperature    172.99(10)
_cell_measurement_theta_max      75.9460
_cell_measurement_theta_min      4.8770
_cell_volume                     1562.82(4)
_computing_cell_refinement       'CrysAlisPro 1.171.42.55a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.55a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.55a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.5 (Bourhis et al., 2015)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      172.99(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.9979
_diffrn_measured_fraction_theta_max 0.9544
_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     33.00  72.00   0.50    0.53    --  104.75 -99.00-180.00   78
  2  \w     75.00 106.00   0.50    0.53    --  104.75 -99.00-180.00   62
  3  \w     37.00  94.00   0.50    0.13    --   47.56-125.00-180.00  114
  4  \w     42.00  70.00   0.50    0.53    --  104.75 -99.00 -90.00   56
  5  \w     74.00 100.00   0.50    0.53    --  104.75 -99.00 -90.00   52
  6  \w     77.00 106.00   0.50    0.53    --  104.75 -99.00 -30.00   58
  7  \w     43.00  68.00   0.50    0.53    --  104.75 -99.00 -30.00   50
  8  \w    -24.00   1.00   0.50    0.13    --   47.56 -11.00 -11.00   50
  9  \w     59.00 106.00   0.50    0.53    --  104.75 -99.00  90.00   94
 10  \w     40.00  65.00   0.50    0.53    --  104.75 -57.00 150.00   50
 11  \w     52.00 109.00   0.50    0.13    --   47.56  11.00 161.00  114
 12  \w     94.00 150.00   0.50    0.53    --  104.75  11.00 161.00  112
 13  \w     96.00 177.00   0.50    0.53    --  104.75  38.00-120.00  162
 14  \w    -57.00 -32.00   0.50    0.53    -- -104.00  57.00 150.00   50
 15  \w    -64.00 -33.00   0.50    0.53    -- -104.00  57.00  90.00   62
 16  \w    -64.00 -38.00   0.50    0.53    -- -104.00  57.00 -30.00   52
 17  \w    -60.00 -34.00   0.50    0.53    -- -104.00  57.00 -60.00   52
 18  \w    -19.00  25.00   0.50    0.13    --  -47.56  11.00 161.00   88
 19  \w    -25.00  21.00   0.50    0.13    --  -47.56  19.00 -60.00   92
 20  \w    -63.00 -32.00   0.50    0.53    -- -104.00  57.00-150.00   62
 21  \w    -58.00 -33.00   0.50    0.53    -- -104.00  57.00-180.00   50
 22  \w    -60.00 -32.00   0.50    0.53    -- -104.00  57.00-120.00   56
 23  \w   -151.00 -93.00   0.50    0.53    -- -104.00 -11.00 -11.00  116
 24  \w   -172.00-146.00   0.50    0.53    -- -104.00 -19.00  60.00   52
 25  \w   -122.00 -93.00   0.50    0.53    -- -104.00 -19.00  60.00   58
 26  \w   -118.00 -55.00   0.50    0.13    --  -47.56 -11.00 -11.00  126
;
_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      -0.0972083000
_diffrn_orient_matrix_UB_12      0.0061941000
_diffrn_orient_matrix_UB_13      0.0661897000
_diffrn_orient_matrix_UB_21      -0.1594797000
_diffrn_orient_matrix_UB_22      0.0214986000
_diffrn_orient_matrix_UB_23      -0.0534974000
_diffrn_orient_matrix_UB_31      -0.0278431000
_diffrn_orient_matrix_UB_32      -0.1450262000
_diffrn_orient_matrix_UB_33      -0.0050863000
_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  0.0290
_diffrn_reflns_av_unetI/netI     0.0303
_diffrn_reflns_Laue_measured_fraction_full 0.9979
_diffrn_reflns_Laue_measured_fraction_max 0.9544
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            10560
_diffrn_reflns_point_group_measured_fraction_full 0.9979
_diffrn_reflns_point_group_measured_fraction_max 0.9544
_diffrn_reflns_theta_full        67.6840
_diffrn_reflns_theta_max         76.64
_diffrn_reflns_theta_min         4.87
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.484
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.91510
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.55a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear yellowish yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.113
_exptl_crystal_description       block
_exptl_crystal_F_000             562.002
_refine_diff_density_max         1.8220
_refine_diff_density_min         -0.9521
_refine_diff_density_rms         0.1122
_refine_ls_d_res_high            0.7924
_refine_ls_d_res_low             9.0767
_refine_ls_goodness_of_fit_ref   1.0224
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    30
_refine_ls_number_parameters     168
_refine_ls_number_reflns         3142
_refine_ls_number_restraints     18
_refine_ls_restrained_S_all      149.8439
_refine_ls_R_factor_all          0.0885
_refine_ls_R_factor_gt           0.0831
_refine_ls_shift/su_max          1992.6366
_refine_ls_shift/su_mean         42.1784
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1417P)^2^+3.7492P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2282
_refine_ls_wR_factor_ref         0.2336
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              8
_reflns_limit_h_min              -10
_reflns_limit_k_max              12
_reflns_limit_k_min              0
_reflns_limit_l_max              23
_reflns_limit_l_min              -8
_reflns_number_gt                2829
_reflns_number_total             3142
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            d4cc04750h2.cif
_cod_data_source_block           DLK1128_auto
_cod_depositor_comments          'Adding full bibliography for 7133791.cif.'
_cod_database_code               7133791
_chemical_oxdiff_formula         'C H O N P'
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C1) \\sim Ueq, Uanis(C2) \\sim Ueq, Uanis(C15) \\sim Ueq: with sigma of 0
and sigma for terminal atoms of 0
3.a Aromatic/amide H refined with riding coordinates:
 N1(H1), N3(H3), C4(H4), C7(H7), C9(H9), C10(H10), C12(H12)
3.b Idealised Me refined as rotating group:
 C5(H5a,H5b,H5c), C8(H8a,H8b,H8c), C13(H13a,H13b,H13c), C15(H15a,H15b,H15c)
;
_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 1.679
_oxdiff_exptl_absorpt_empirical_full_min 0.866