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_7132696
_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         'C29 H21 O2 P'
_chemical_formula_sum            'C29 H21 O2 P'
_chemical_formula_weight         432.43
_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   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                90
_cell_angle_beta                 109.249(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.4750(2)
_cell_length_b                   18.8265(3)
_cell_length_c                   12.4890(2)
_cell_measurement_reflns_used    8924
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      76.6400
_cell_measurement_theta_min      4.4280
_cell_volume                     2103.26(7)
_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    -26.00   3.00   0.50    0.07    --   47.45 -19.00   0.00   58
  2  \w    -20.00   5.00   0.50    0.07    --   47.45 -19.00 -30.00   50
  3  \w    -24.00  20.00   0.50    0.07    --   47.45 -37.00 -90.00   88
  4  \w    -27.00   2.00   0.50    0.07    --   47.45 -19.00-120.00   58
  5  \w    -23.00   5.00   0.50    0.07    --   47.45 -19.00-150.00   56
  6  \w     39.00  64.00   0.50    0.29    --   86.25-123.00-176.00   50
  7  \w     12.00  37.00   0.50    0.07    --   47.45-123.00-176.00   50
  8  \w     27.00  53.00   0.50    0.07    --   47.45-149.00  19.00   52
  9  \w   -127.00 -95.00   0.50    0.29    -- -107.75 -19.00-120.00   64
 10  \w   -177.00-151.00   0.50    0.29    -- -107.75 -19.00-120.00   52
 11  \w   -174.00-102.00   0.50    0.29    -- -107.75 -37.00 -90.00  144
 12  \w   -143.00 -76.00   0.50    0.29    -- -107.75-123.00-176.00  134
 13  \w   -113.00 -88.00   0.50    0.07    --  -47.45-149.00  19.00   50
 14  \w   -136.00-110.00   0.50    0.29    -- -107.75-149.00  19.00   52
 15  \w   -121.00 -94.00   0.50    0.29    -- -107.75  77.00 -90.00   54
 16  \w    -82.00 -36.00   0.50    0.29    -- -107.75  57.00 -90.00   92
 17  \w    -63.00 -35.00   0.50    0.29    -- -107.75  37.00-120.00   56
 18  \w    -61.00 -36.00   0.50    0.29    -- -107.75  37.00-150.00   50
 19  \w    -87.00 -38.00   0.50    0.29    -- -107.75  77.00 -90.00   98
 20  \w    -81.00 -47.00   0.50    0.29    -- -107.75  57.00 -30.00   68
 21  \w    -59.00 -34.00   0.50    0.29    -- -107.75  37.00 -30.00   50
 22  \w    -61.00 -36.00   0.50    0.29    -- -107.75  37.00  90.00   50
 23  \w    -63.00 -34.00   0.50    0.29    -- -107.75  37.00 120.00   58
 24  \w    -59.00 -34.00   0.50    0.29    -- -107.75  37.00 150.00   50
 25  \w   -108.00 -25.00   0.50    0.07    --  -47.45 149.00  67.00  166
 26  \w   -128.00 -96.00   0.50    0.29    -- -107.75 147.00 146.94   64
 27  \w   -112.00 -55.00   0.50    0.29    -- -107.75 149.00  67.00  114
 28  \w   -110.00 -71.00   0.50    0.29    -- -107.75 123.00 -96.00   78
 29  \w     91.00 116.00   0.50    0.29    --   86.25 123.00 -96.00   50
 30  \w    106.00 131.00   0.50    0.29    --   86.25 149.00  67.00   50
 31  \w     57.00  82.00   0.50    0.07    --   47.45 149.00  67.00   50
;
_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      -0.0068023000
_diffrn_orient_matrix_UB_12      -0.0591916000
_diffrn_orient_matrix_UB_13      0.0833035000
_diffrn_orient_matrix_UB_21      -0.0151543000
_diffrn_orient_matrix_UB_22      -0.0560253000
_diffrn_orient_matrix_UB_23      -0.0930344000
_diffrn_orient_matrix_UB_31      0.1714463000
_diffrn_orient_matrix_UB_32      -0.0073244000
_diffrn_orient_matrix_UB_33      0.0383498000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0398
_diffrn_reflns_av_unetI/netI     0.0374
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.965
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            15613
_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         77.252
_diffrn_reflns_theta_min         4.425
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.352
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.95790
_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    1.366
_exptl_crystal_description       plate
_exptl_crystal_F_000             904
_exptl_crystal_size_max          0.152
_exptl_crystal_size_mid          0.144
_exptl_crystal_size_min          0.086
_refine_diff_density_max         0.297
_refine_diff_density_min         -0.345
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     290
_refine_ls_number_reflns         4299
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0421
_refine_ls_R_factor_gt           0.0377
_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^)+(0.0543P)^2^+0.6245P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1013
_refine_ls_wR_factor_ref         0.1052
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3829
_reflns_number_total             4299
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3cc05994d2.cif
_cod_data_source_block           530_autored
_cod_depositor_comments
'Adding full bibliography for 7132694--7132697.cif.'
_cod_original_cell_volume        2103.25(7)
_cod_database_code               7132696
_shelx_shelxl_version_number     2017/1
_chemical_oxdiff_formula         'C29 H24 O2 P1'
_shelx_estimated_absorpt_t_max   0.888
_shelx_estimated_absorpt_t_min   0.823
_diffrn_oxdiff_digest_frames
;
0136be669346bc33d0491c6eeadab809b10215683cb
;
_diffrn_oxdiff_digest_hkl
;
01af5f2d4c2c07191b85b26305586868b26067
;
_reflns_odcompleteness_completeness 99.93
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     68.13
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C00E(H00E), C00F(H00F), C00G(H00G), C00H(H00H), C00I(H00I), C00J(H00J),
 C00K(H00K), C00L(H00L), C00M(H00M), C00N(H00N), C00O(H00O), C00P(H00P),
 C00Q(H00Q), C00R(H00R), C00S(H00S), C00T(H00T), C00U(H00U), C00V(H00V)
2.b Idealised Me refined as rotating group:
 C00W(H00A,H00B,H00C)
;
_shelx_res_checksum              62019
_shelx_hkl_checksum              62196
_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 1.366
_oxdiff_exptl_absorpt_empirical_full_min 0.796