The significance of phosphoniocarbynes in halocarbyne cross-coupling reactions.
Burt, Liam K.; Cordiner, Richard L.; Hill, Anthony F.; Manzano, Richard A.; Wagler, Jörg; Chemical communications (Cambridge, England) 56 (2020) 5673–5676; doi:10.1039/d0cc02070b

data_7126402
_publ_section_title
;
 The significance of phosphoniocarbynes in halocarbyne cross-coupling
 reactions.
;
_journal_issue                   42
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              5673
_journal_page_last               5676
_journal_paper_doi               10.1039/d0cc02070b
_journal_volume                  56
_journal_year                    2020
_chemical_formula_moiety         'C54 H52 B Br N6 O2 P2 Pd W'
_chemical_formula_sum            'C52 H52 B Br N6 O2 P2 Pd W'
_chemical_formula_weight         1235.90
_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     dual
_audit_creation_date             2019-05-28
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-03-06 deposited with the CCDC.	2020-04-08 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 111.409(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   21.7995(4)
_cell_length_b                   12.8236(2)
_cell_length_c                   22.8740(4)
_cell_measurement_reflns_used    16669
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      73.6170
_cell_measurement_theta_min      4.0180
_cell_volume                     5953.2(2)
_computing_cell_refinement       'CrysAlisPro 1.171.40.36a (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.40.36a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.36a (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.1297
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.991
_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    -82.00 -48.00   1.00    7.50    --  -37.08 -38.00  30.00   34
  2  \w     60.00 101.00   1.00    7.50    --   37.08  57.00-150.00   41
  3  \w     22.00  49.00   1.00    7.50    --   37.08 -57.00  60.00   27
  4  \w    -17.00  10.00   1.00    7.50    --   37.08 -57.00-150.00   27
  5  \w    -29.00  -3.00   1.00    7.50    --   37.08 -57.00  60.00   26
  6  \w     36.00  84.00   1.00    7.50    --   37.08-125.00-150.00   48
  7  \w     29.00  58.00   1.00    7.50    --   37.08  57.00-150.00   29
  8  \w     -8.00  65.00   1.00    7.50    --   37.08 -19.00 -90.00   73
  9  \w     15.00  51.00   1.00    7.50    --   37.08 -57.00-150.00   36
 10  \w     39.00  64.00   1.00    7.50    --   37.08 -77.00  60.00   25
 11  \w    -17.00  51.00   1.00    7.50    --   37.08 -38.00-120.00   68
 12  \w     34.00  61.00   1.00    7.50    --   37.08-125.00 150.00   27
 13  \w     86.00 136.00   1.00   30.00    --  111.00 -25.00 120.00   50
 14  \w    131.00 168.00   1.00   30.00    --  111.00  12.00  90.00   37
 15  \w    109.00 176.00   1.00   30.00    --  111.00  38.00 -30.00   67
 16  \w     68.00 118.00   1.00   30.00    --  111.00  12.00  90.00   50
 17  \w     63.00 109.00   1.00   30.00    --  111.00-111.00 150.00   46
 18  \w     43.00  86.00   1.00   30.00    --  111.00 -92.00-120.00   43
 19  \w     62.00 104.00   1.00   30.00    --  111.00 178.00 -30.00   42
 20  \w     42.00 104.00   1.00   30.00    --  111.00 -92.00-150.00   62
 21  \w     98.00 125.00   1.00   30.00    --  111.00 -38.00 -30.00   27
 22  \w    109.00 163.00   1.00   30.00    --  111.00 111.00 150.00   54
 23  \w     42.00  82.00   1.00   30.00    --  111.00 -38.00 -30.00   40
 24  \w    102.00 129.00   1.00   30.00    --  111.00  64.00 -60.00   27
 25  \w    150.00 176.00   1.00   30.00    --  111.00  64.00 -60.00   26
 26  \w     45.00  70.00   1.00   30.00    --  111.00-111.00   0.00   25
 27  \w     76.00 130.00   1.00   30.00    --  111.00 -66.00 -98.14   54
 28  \w     72.00 100.00   1.00   30.00    --  111.00 -77.00 120.00   28
 29  \w    100.00 133.00   1.00   30.00    --  111.00 -25.00 -30.00   33
 30  \w     80.00 105.00   1.00   30.00    --  111.00-111.00  30.00   25
 31  \w     48.00  75.00   1.00   30.00    --  111.00-111.00  30.00   27
 32  \w     81.00 106.00   1.00   30.00    --  111.00 -92.00-180.00   25
 33  \w     48.00  75.00   1.00   30.00    --  111.00 -92.00-180.00   27
 34  \w     71.00 119.00   1.00   30.00    --  111.00 -64.00 150.00   48
 35  \w    123.00 160.00   1.00   30.00    --  111.00  38.00-180.00   37
 36  \w     60.00 127.00   1.00   30.00    --  111.00 -50.00-180.00   67
 37  \w    104.00 177.00   1.00   30.00    --  111.00  77.00 -90.00   73
 38  \w    126.00 159.00   1.00   30.00    --  111.00  25.00 -60.00   33
 39  \w     50.00  89.00   1.00   30.00    --  111.00 -92.00 -90.00   39
 40  \w     56.00  81.00   1.00   30.00    --  111.00 -25.00 -30.00   25
 41  \w     81.00 106.00   1.00   30.00    --  111.00-111.00   0.00   25
 42  \w     84.00 109.00   1.00   30.00    --  111.00-111.00 120.00   25
 43  \w     56.00  83.00   1.00   30.00    --  111.00 -50.00-120.00   27
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, EosS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0455167000
_diffrn_orient_matrix_UB_12      0.0063843000
_diffrn_orient_matrix_UB_13      -0.0379331000
_diffrn_orient_matrix_UB_21      0.0607153000
_diffrn_orient_matrix_UB_22      -0.0006429000
_diffrn_orient_matrix_UB_23      0.0615786000
_diffrn_orient_matrix_UB_31      0.0021370000
_diffrn_orient_matrix_UB_32      -0.1199338000
_diffrn_orient_matrix_UB_33      -0.0023991000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0583
_diffrn_reflns_av_unetI/netI     0.0561
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            45204
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.760
_diffrn_reflns_theta_min         4.024
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    7.556
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.83182
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.36a (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light red'
_exptl_crystal_density_diffrn    1.379
_exptl_crystal_description       plate
_exptl_crystal_F_000             2448
_exptl_crystal_size_max          0.172
_exptl_crystal_size_mid          0.134
_exptl_crystal_size_min          0.037
_refine_diff_density_max         2.886
_refine_diff_density_min         -1.940
_refine_diff_density_rms         0.146
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     619
_refine_ls_number_reflns         11926
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0617
_refine_ls_R_factor_gt           0.0505
_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^)+(0.0545P)^2^+29.4186P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1278
_refine_ls_wR_factor_ref         0.1347
_reflns_Friedel_coverage         0.000
_reflns_number_gt                9743
_reflns_number_total             11926
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0cc02070b3.cif
_cod_data_source_block           7
_cod_depositor_comments
'Adding full bibliography for 7126395--7126402.cif.'
_cod_original_cell_volume        5953.16(19)
_cod_database_code               7126402
_publcif_datablock.id            {22d23fa7-6121-4349-b642-2831eeb9a4c9}
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         C52H52B1N6O2P2Br1W1Pd1
_chemical_oxdiff_usercomment     'Vap. Diff. n-hex into THF'
_reflns_odcompleteness_completeness 98.01
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All B(H) groups, All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 B1(H1)
2.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C11(H11), C16(H16), C21(H21), C22(H22), C23(H23), C24(H24), C25(H25),
 C31(H31), C32(H32), C33(H33), C34(H34), C35(H35), C41(H41), C42(H42), C43(H43),
  C44(H44), C45(H45), C51(H51), C52(H52), C53(H53), C54(H54), C55(H55),
 C61(H61), C62(H62), C63(H63), C64(H64), C65(H65), C71(H71), C72(H72), C73(H73),
  C74(H74), C75(H75)
2.c Idealised Me refined as rotating group:
 C4(H4A,H4B,H4C), C8(H8A,H8B,H8C), C9(H9A,H9B,H9C), C13(H13A,H13B,H13C),
 C14(H14A,H14B,H14C), C18(H18A,H18B,H18C)
;
_shelx_res_checksum              97597
_shelx_hkl_checksum              79654
_shelx_fab_checksum              47792
_ins_header
;
TITL LB009_scale_filt in P2(1)/n 
REM P2(1)/n (#14 in standard setting)
CELL 1.54184  21.799505  12.823648  22.874023  90.0000 111.4086  90.0000
ZERR    4.00   0.000415   0.000209   0.000435   0.0000   0.0022   0.0000
LATT  1
SYMM -x+1/2, y+1/2,-z+1/2 
SFAC C H B N O P Br Pd W
UNIT 208.00 208.00 4.00 24.00 8.00 8.00 4.00 4.00 4.00
TREF
HKLF 4
END
;
_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 1.467
_oxdiff_exptl_absorpt_empirical_full_min 0.753
_publcif_funding_html
;
;