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_7132697
_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 H22 N3 O P'
_chemical_formula_sum            'C29 H22 N3 O P'
_chemical_formula_weight         459.46
_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             2023-07-27
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2023-07-31 deposited with the CCDC.	2024-02-09 downloaded from the CCDC.
;
_cell_angle_alpha                77.043(2)
_cell_angle_beta                 86.915(2)
_cell_angle_gamma                82.273(2)
_cell_formula_units_Z            4
_cell_length_a                   9.9714(2)
_cell_length_b                   10.8463(2)
_cell_length_c                   22.5248(4)
_cell_measurement_reflns_used    20145
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      76.7580
_cell_measurement_theta_min      4.0290
_cell_volume                     2351.83(8)
_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 0.998
_diffrn_measured_fraction_theta_max 0.953
_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    -25.00   2.00   0.50    0.15    --   47.45 -19.00-180.00   54
  2  \w    -25.00  20.00   0.50    0.15    --   47.45 -37.00-180.00   90
  3  \w    -23.00  20.00   0.50    0.15    --   47.45 -37.00 -90.00   86
  4  \w    -21.00   5.00   0.50    0.15    --   47.45 -19.00-120.00   52
  5  \w    -25.00   0.00   0.50    0.15    --   47.45 -19.00-150.00   50
  6  \w    -25.00   3.00   0.50    0.15    --   47.45 -19.00  30.00   56
  7  \w    -26.00   0.00   0.50    0.15    --   47.45 -19.00  60.00   52
  8  \w    -26.00   4.00   0.50    0.15    --   47.45 -19.00 120.00   60
  9  \w    -27.00   2.00   0.50    0.15    --   47.45 -19.00 150.00   58
 10  \w     14.00  42.00   0.50    0.60    --   86.25 -57.00 -30.00   56
 11  \w     62.00  88.00   0.50    0.60    --   86.25-138.00-168.00   52
 12  \w     37.00  62.00   0.50    0.15    --   47.45-138.00-168.00   50
 13  \w     14.00  39.00   0.50    0.60    --   86.25 -57.00-150.00   50
 14  \w     17.00 114.00   0.50    0.60    --   86.25-131.00   7.00  194
 15  \w     14.00  40.00   0.50    0.60    --   86.25 -57.00 150.00   52
 16  \w     45.00  96.00   0.50    0.15    --   47.45-131.00   7.00  102
 17  \w   -127.00 -94.00   0.50    0.60    -- -106.49 -37.00 -90.00   66
 18  \w   -173.00-147.00   0.50    0.60    -- -106.49 -37.00 -90.00   52
 19  \w   -134.00-105.00   0.50    0.60    -- -106.49 -19.00  60.00   58
 20  \w   -168.00 -94.00   0.50    0.60    -- -106.49 -19.00  90.00  148
 21  \w   -174.00-142.00   0.50    0.60    -- -106.49 -19.00  60.00   64
 22  \w   -154.00-111.00   0.50    0.60    -- -106.49 -99.00  30.00   86
 23  \w   -109.00 -74.00   0.50    0.60    -- -106.49-131.00   7.00   70
 24  \w   -118.00 -93.00   0.50    0.15    --  -47.45-131.00   7.00   50
 25  \w   -144.00-119.00   0.50    0.60    -- -106.49-138.00-168.00   50
 26  \w   -175.00-133.00   0.50    0.60    -- -106.49-125.00-120.00   84
 27  \w   -127.00 -75.00   0.50    0.60    -- -106.49-125.00-120.00  104
 28  \w    -95.00 -70.00   0.50    0.15    --  -47.45-138.00-168.00   50
 29  \w    -59.00 -33.00   0.50    0.60    -- -106.49  37.00  60.00   52
 30  \w    -70.00 -45.00   0.50    0.60    -- -106.49  57.00  90.00   50
 31  \w   -126.00-100.00   0.50    0.60    -- -106.49  77.00 -90.00   52
 32  \w    -92.00 -39.00   0.50    0.60    -- -106.49  77.00 -90.00  106
 33  \w    -87.00 -34.00   0.50    0.60    -- -106.49  57.00-150.00  106
 34  \w    -87.00 -34.00   0.50    0.60    -- -106.49  57.00 -90.00  106
 35  \w    -61.00 -35.00   0.50    0.60    -- -106.49  37.00-120.00   52
 36  \w    -63.00 -38.00   0.50    0.60    -- -106.49  37.00 -90.00   50
 37  \w    -63.00 -34.00   0.50    0.60    -- -106.49  37.00 -30.00   58
 38  \w    -62.00 -37.00   0.50    0.60    -- -106.49  37.00  30.00   50
 39  \w    -83.00 -34.00   0.50    0.60    -- -106.49  57.00  60.00   98
 40  \w    -63.00 -38.00   0.50    0.60    -- -106.49  37.00 120.00   50
 41  \w   -101.00 -40.00   0.50    0.60    -- -106.49 125.00  60.00  122
 42  \w   -115.00 -36.00   0.50    0.60    -- -106.49 131.00  77.00  158
 43  \w   -110.00 -53.00   0.50    0.60    -- -106.49 125.00  30.00  114
 44  \w    -81.00 -56.00   0.50    0.15    --  -47.45 131.00  77.00   50
 45  \w   -100.00 -52.00   0.50    0.15    --  -47.45 138.00-106.00   96
 46  \w   -106.00 -81.00   0.50    0.60    -- -106.49 125.00-180.00   50
 47  \w   -119.00 -36.00   0.50    0.60    -- -106.49 138.00-106.00  166
 48  \w     66.00 119.00   0.50    0.15    --   47.45 138.00-106.00  106
 49  \w     91.00 117.00   0.50    0.60    --   86.25 138.00-106.00   52
 50  \w     79.00 114.00   0.50    0.60    --   86.25 131.00  77.00   70
 51  \w     70.00 117.00   0.50    0.15    --   47.45 131.00  77.00   94
;
_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      -0.0135559000
_diffrn_orient_matrix_UB_12      0.0734105000
_diffrn_orient_matrix_UB_13      0.0516168000
_diffrn_orient_matrix_UB_21      0.0144691000
_diffrn_orient_matrix_UB_22      -0.1272563000
_diffrn_orient_matrix_UB_23      0.0475527000
_diffrn_orient_matrix_UB_31      0.1546944000
_diffrn_orient_matrix_UB_32      -0.0002924000
_diffrn_orient_matrix_UB_33      -0.0016589000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0453
_diffrn_reflns_av_unetI/netI     0.0433
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.953
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            31902
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.953
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.868
_diffrn_reflns_theta_min         4.029
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.246
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.89949
_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            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.298
_exptl_crystal_description       block
_exptl_crystal_F_000             960
_exptl_crystal_size_max          0.347
_exptl_crystal_size_mid          0.107
_exptl_crystal_size_min          0.085
_refine_diff_density_max         0.723
_refine_diff_density_min         -0.375
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     613
_refine_ls_number_reflns         9481
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0464
_refine_ls_R_factor_gt           0.0417
_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^)+(0.0625P)^2^+0.7168P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1109
_refine_ls_wR_factor_ref         0.1152
_reflns_Friedel_coverage         0.000
_reflns_number_gt                8406
_reflns_number_total             9481
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3cc05994d2.cif
_cod_data_source_block           469_autored
_cod_depositor_comments
;
Adding full bibliography for 7132694--7132697.cif.

2024-12-16
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C58 H44 N6 O2 P2'
_cod_original_formula_weight         918.93
_cod_original_formula_moiety         '2(C29 H22 N3 O P)'
_cod_original_formula_units_Z            2
_cod_database_code               7132697
_shelx_shelxl_version_number     2017/1
_chemical_oxdiff_formula         'C29 H22 O1 N3 P1'
_shelx_estimated_absorpt_t_max   0.896
_shelx_estimated_absorpt_t_min   0.670
_diffrn_oxdiff_digest_frames
;
01b91f37b3cdbc6fda05ee72c29c33e68a03904b9f9
;
_diffrn_oxdiff_digest_hkl
;
012ac914adc493be0c434980d5bdd216a3757b
;
_reflns_odcompleteness_completeness 99.89
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C015(H01H,H01I), C019(H01A,H01B)
2.b Aromatic/amide H refined with riding coordinates:
 C00H(H00H), C00O(H00O), C00Q(H00Q), C00R(H00R), C00S(H00S), C00T(H00T),
 C00V(H00V), C00W(H00W), C00X(H00X), C00Y(H00Y), C00Z(H00Z), C011(H011),
 C012(H012), C013(H013), C014(H014), C016(H016), C018(H018), C01A(H01K),
 C01B(H01C), C01C(H01D), C01D(H01N), C01E(H01E), C01F(H01F), C01G(H01G),
 C01H(H01O), C01I(H01P), C01J(H01J), C01K(H01Q), C01L(H01L), C01M(H01M),
 C01N(H01S), C01O(H01T), C01P(H01U), C01Q(H01X), C01R(H01R), C01S(H01Y),
 C01T(H01Z), C01U(H01), C01V(H01V), C01W(H01W)
;
_shelx_res_checksum              1220
_shelx_hkl_checksum              30471
_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 1.413
_oxdiff_exptl_absorpt_empirical_full_min 0.638