Pd-catalysed C-H alkynylation of benzophospholes.
Tokura, Yu; Xu, Shibo; Yasui, Kosuke; Nishii, Yuji; Hirano, Koji; Chemical communications (Cambridge, England) 60 (2024) 2792–2795; doi:10.1039/d3cc05994d

data_7132695
_publ_section_title
;
 Pd-catalysed C-H alkynylation of benzophospholes.
;
_journal_issue                   20
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              2792
_journal_page_last               2795
_journal_paper_doi               10.1039/d3cc05994d
_journal_volume                  60
_journal_year                    2024
_chemical_formula_moiety         'C44 H30 O2 P2 S, 2(C H Cl3)'
_chemical_formula_sum            'C46 H32 Cl6 O2 P2 S'
_chemical_formula_weight         923.41
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-07-20
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2023-07-20 deposited with the CCDC.	2024-02-09 downloaded from the CCDC.
;
_cell_angle_alpha                118.189(2)
_cell_angle_beta                 92.5060(10)
_cell_angle_gamma                114.771(2)
_cell_formula_units_Z            2
_cell_length_a                   14.0465(2)
_cell_length_b                   14.1358(2)
_cell_length_c                   14.4268(2)
_cell_measurement_reflns_used    16328
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      76.6150
_cell_measurement_theta_min      3.6020
_cell_volume                     2185.50(10)
_computing_cell_refinement       'CrysAlisPro 1.171.42.81a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.81a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.81a (Rigaku OD, 2023)'
_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_temperature      123(2)
_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 0.965
_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    -24.00   2.00   0.50    0.05    --   47.45 -19.00 150.00   52
  2  \w    -24.00   3.00   0.50    0.05    --   47.45 -62.00 123.00   54
  3  \w     21.00  47.00   0.50    0.05    --   47.45 -62.00 123.00   52
  4  \w    -27.00  -2.00   0.50    0.05    --   47.45 -19.00 -30.00   50
  5  \w     15.00  62.00   0.50    0.13    --   86.25 -77.00   0.00   94
  6  \w     15.00  42.00   0.50    0.13    --   86.25 -57.00 -60.00   54
  7  \w     14.00  40.00   0.50    0.13    --   86.25 -57.00  30.00   52
  8  \w     26.00  51.00   0.50    0.13    --   86.25 -62.00 123.00   50
  9  \w     40.00 116.00   0.50    0.05    --   47.45  62.00 -99.00  152
 10  \w     18.00  89.00   0.50    0.05    --   47.45-125.00 150.00  142
 11  \w     75.00 101.00   0.50    0.13    --   86.25  62.00 -99.00   52
 12  \w    127.00 153.00   0.50    0.13    --   86.25  62.00 -99.00   52
 13  \w     -3.00  23.00   0.50    0.05    --  -47.45  62.00 -99.00   52
 14  \w    -61.00 -15.00   0.50    0.05    --  -47.45  62.00 -99.00   92
 15  \w   -123.00 -75.00   0.50    0.13    -- -107.75 140.00  19.10   96
 16  \w   -110.00 -62.00   0.50    0.13    -- -107.75 125.00  90.00   96
 17  \w    -81.00 -40.00   0.50    0.13    -- -107.75 133.00 -10.52   82
 18  \w    -76.00 -38.00   0.50    0.13    -- -107.75 125.00  60.00   76
 19  \w   -109.00 -70.00   0.50    0.13    -- -107.75 125.00 -60.00   78
 20  \w    -66.00 -41.00   0.50    0.13    -- -107.75 125.00 -60.00   50
 21  \w   -111.00 -44.00   0.50    0.13    -- -107.75 125.00 -90.00  134
 22  \w   -109.00 -84.00   0.50    0.13    -- -107.75 125.00  60.00   50
 23  \w    -88.00 -18.00   0.50    0.05    --  -47.45 125.00-120.00  140
 24  \w    -71.00 -42.00   0.50    0.13    -- -107.75 125.00-150.00   58
 25  \w   -107.00 -67.00   0.50    0.13    -- -107.75 125.00-180.00   80
 26  \w   -106.00 -62.00   0.50    0.13    -- -107.75 105.00-147.52   88
 27  \w    -84.00 -44.00   0.50    0.13    -- -107.75  77.00 -90.00   80
 28  \w    -79.00 -36.00   0.50    0.13    -- -107.75  62.00 -99.00   86
 29  \w    -84.00 -39.00   0.50    0.13    -- -107.75  57.00-180.00   90
 30  \w    -86.00 -48.00   0.50    0.13    -- -107.75  57.00-120.00   76
 31  \w   -123.00 -97.00   0.50    0.13    -- -107.75  77.00 -90.00   52
 32  \w    -62.00 -34.00   0.50    0.13    -- -107.75  37.00 -90.00   56
 33  \w    -87.00 -62.00   0.50    0.13    -- -107.75  57.00  90.00   50
 34  \w    -74.00 -48.00   0.50    0.13    -- -107.75  57.00 120.00   52
 35  \w    -62.00 -34.00   0.50    0.13    -- -107.75  37.00  90.00   56
 36  \w    -63.00 -35.00   0.50    0.13    -- -107.75  37.00 120.00   56
 37  \w    -63.00 -36.00   0.50    0.13    -- -107.75  37.00  60.00   54
 38  \w    -60.00 -34.00   0.50    0.13    -- -107.75  37.00   0.00   52
 39  \w    -63.00 -35.00   0.50    0.13    -- -107.75  37.00-150.00   56
 40  \w    -61.00 -35.00   0.50    0.13    -- -107.75  37.00 -30.00   52
 41  \w   -116.00 -34.00   0.50    0.05    --  -47.45 -62.00 123.00  164
 42  \w   -161.00-107.00   0.50    0.13    -- -107.75 -62.00 123.00  108
 43  \w   -138.00 -99.00   0.50    0.13    -- -107.75 -19.00   0.00   78
 44  \w   -170.00-120.00   0.50    0.13    -- -107.75 -19.00 150.00  100
 45  \w   -169.00 -96.00   0.50    0.13    -- -107.75 -37.00 -90.00  146
 46  \w   -133.00 -99.00   0.50    0.13    -- -107.75 -37.00-180.00   68
 47  \w   -161.00-135.00   0.50    0.13    -- -107.75 -37.00-180.00   52
 48  \w   -115.00 -87.00   0.50    0.13    -- -107.75-125.00-120.00   56
 49  \w   -166.00-120.00   0.50    0.13    -- -107.75-125.00-120.00   92
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'XtaLAB Synergy, Single source at offset/far, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0903311000
_diffrn_orient_matrix_UB_12      0.1368528000
_diffrn_orient_matrix_UB_13      0.0763571000
_diffrn_orient_matrix_UB_21      0.0187746000
_diffrn_orient_matrix_UB_22      -0.0227277000
_diffrn_orient_matrix_UB_23      0.0918980000
_diffrn_orient_matrix_UB_31      0.0868429000
_diffrn_orient_matrix_UB_32      -0.0334772000
_diffrn_orient_matrix_UB_33      -0.0433049000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0462
_diffrn_reflns_av_unetI/netI     0.0440
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.965
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            29245
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.965
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.314
_diffrn_reflns_theta_min         3.635
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    5.027
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.55566
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.81a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.403
_exptl_crystal_description       block
_exptl_crystal_F_000             944
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.12
_refine_diff_density_max         1.302
_refine_diff_density_min         -1.006
_refine_diff_density_rms         0.066
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     514
_refine_ls_number_reflns         8948
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.068
_refine_ls_R_factor_all          0.0496
_refine_ls_R_factor_gt           0.0450
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0575P)^2^+1.3924P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1195
_refine_ls_wR_factor_ref         0.1234
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7935
_reflns_number_total             8948
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3cc05994d2.cif
_cod_data_source_block           534_down_autored
_cod_depositor_comments
'Adding full bibliography for 7132694--7132697.cif.'
_cod_original_cell_volume        2185.49(7)
_cod_database_code               7132695
_shelx_shelxl_version_number     2017/1
_chemical_oxdiff_formula         'C44 H30 O2 P2 S1'
_shelx_estimated_absorpt_t_max   0.584
_shelx_estimated_absorpt_t_min   0.280
_diffrn_oxdiff_digest_frames
;
013412b54894d05e5ef26bfefa1b36c6f2037603f41
;
_diffrn_oxdiff_digest_hkl
;
017401cc9777f8a7ee97805f69d9eac9f0ecc0
;
_reflns_odcompleteness_completeness 99.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     68.13
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Ternary CH refined with riding coordinates:
 C01K(H01K), C01L(H01L)
2.b Aromatic/amide H refined with riding coordinates:
 C00H(H00H), C00I(H00I), C00P(H00P), C00T(H00T), C00U(H00U), C00V(H00V),
 C00W(H00W), C00X(H00X), C00Y(H00Y), C00Z(H00Z), C010(H010), C011(H011),
 C012(H012), C013(H013), C014(H014), C015(H015), C016(H016), C017(H017),
 C018(H018), C019(H019), C01A(H01A), C01B(H01B), C01C(H01C), C01D(H01D),
 C01E(H01E), C01F(H01F), C01G(H01G), C01H(H01H), C01I(H01I), C01J(H01J)
;
_shelx_res_checksum              90514
_shelx_hkl_checksum              24037
_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 1.846
_oxdiff_exptl_absorpt_empirical_full_min 0.664