Palladium-catalyzed alkyne hydrocarbonylation under atmospheric pressure of carbon monoxide in the presence of hydrosilane
Luo, Yu; Wang, Xilong; Liu, Qianwen; He, Yimiao; Li, Jing; Luo, Shuang; Zhu, Qiang; Green Chemistry 25 (2023) 1120–1127; doi:10.1039/D2GC04689J

data_7246186
_publ_section_title
;
 Palladium-catalyzed alkyne hydrocarbonylation under atmospheric pressure
 of carbon monoxide in the presence of hydrosilane
;
_journal_issue                   3
_journal_name_full               'Green Chemistry'
_journal_page_first              1120
_journal_page_last               1127
_journal_paper_doi               10.1039/D2GC04689J
_journal_volume                  25
_journal_year                    2023
_chemical_formula_moiety         'C25 H29 N O'
_chemical_formula_sum            'C25 H29 N O'
_chemical_formula_weight         359.49
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2022-05-05
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2022-08-12 deposited with the CCDC.	2023-01-13 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 103.2920(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   11.2000(2)
_cell_length_b                   7.87450(10)
_cell_length_c                   11.8582(2)
_cell_measurement_reflns_used    16384
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      78.7280
_cell_measurement_theta_min      3.7790
_cell_volume                     1017.81(3)
_computing_cell_refinement       'CrysAlisPro 1.171.41.120a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.120a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.120a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.971
_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     27.00 123.00   0.50    0.05    --   45.81  19.00  60.00  192
  2  \w     21.00 119.00   0.50    0.05    --   45.81  77.00  90.00  196
  3  \w     21.00 119.00   0.50    0.05    --   45.81  77.00  30.00  196
  4  \w     29.00 119.00   0.50    0.05    --   45.81  57.00 -30.00  180
  5  \w     25.00 123.00   0.50    0.05    --   45.81  15.00 -36.00  196
  6  \w    -22.00  31.00   0.50    0.05    --  -45.81  15.00 -36.00  106
  7  \w    -61.00 -27.00   0.50    0.05    -- -100.00  61.00-120.00   68
  8  \w    -57.00 -27.00   0.50    0.05    -- -100.00  61.00  60.00   60
  9  \w    -69.00 -27.00   0.50    0.05    -- -100.00  61.00 120.00   84
 10  \w     89.00 163.00   0.50    0.05    --  112.25  77.00  90.00  148
 11  \w    133.00 177.00   0.50    0.05    --  112.25  61.00  30.00   88
 12  \w     95.00 122.00   0.50    0.05    --  112.25  61.00  30.00   54
 13  \w    100.00 177.00   0.50    0.05    --  112.25  61.00 -30.00  154
 14  \w     91.00 178.00   0.50    0.05    --  112.25  15.00 -36.00  174
 15  \w     79.00 104.00   0.50    0.05    --  112.25 -77.00 -60.00   50
 16  \w     43.00  72.00   0.50    0.05    --  112.25 -61.00-120.00   58
 17  \w     42.00  72.00   0.50    0.05    --  112.25 -61.00 -90.00   60
 18  \w     43.00  73.00   0.50    0.05    --  112.25 -61.00 -60.00   60
 19  \w     41.00  72.00   0.50    0.05    --  112.25 -61.00 -30.00   62
 20  \w     40.00  68.00   0.50    0.05    --  112.25 -61.00  30.00   56
 21  \w    -30.00  26.00   0.50    0.05    --   45.81 -15.00 153.00  112
 22  \w     18.00  96.00   0.50    0.05    --   45.81-125.00  60.00  156
 23  \w     40.00 108.00   0.50    0.05    --  112.25-125.00  60.00  136
 24  \w     64.00 103.00   0.50    0.05    --  112.25 -94.00  30.00   78
 25  \w     79.00 105.00   0.50    0.05    --  112.25-125.00   0.00   52
 26  \w     43.00  76.00   0.50    0.05    --  112.25-125.00   0.00   66
 27  \w     40.00  67.00   0.50    0.05    --  112.25 -94.00 -90.00   54
 28  \w     72.00 104.00   0.50    0.05    --  112.25 -94.00 -90.00   64
 29  \w   -119.00 -21.00   0.50    0.05    --  -45.81 -77.00 120.00  196
 30  \w   -119.00 -21.00   0.50    0.05    --  -45.81 -77.00  60.00  196
 31  \w   -103.00 -77.00   0.50    0.05    -- -100.00 -77.00   0.00   52
 32  \w   -173.00 -75.00   0.50    0.05    -- -100.00 -77.00  60.00  196
 33  \w   -168.00-142.00   0.50    0.05    -- -100.00 -77.00  30.00   52
 34  \w   -116.00 -77.00   0.50    0.05    -- -100.00 -77.00  30.00   78
 35  \w   -158.00-132.00   0.50    0.05    -- -100.00 -77.00 150.00   52
 36  \w   -159.00-122.00   0.50    0.05    -- -100.00 -75.00 128.30   74
 37  \w   -101.00 -75.00   0.50    0.05    -- -100.00 -77.00 150.00   52
 38  \w   -101.00 -76.00   0.50    0.05    -- -100.00 -75.00 128.30   50
 39  \w   -101.00 -75.00   0.50    0.05    -- -100.00 -77.00 120.00   52
 40  \w   -102.00 -77.00   0.50    0.05    -- -100.00 -71.00 152.78   50
 41  \w   -109.00 -77.00   0.50    0.05    -- -100.00 -73.00 118.95   64
 42  \w   -111.00 -75.00   0.50    0.05    -- -100.00 -77.00  90.00   72
 43  \w   -173.00 -77.00   0.50    0.05    -- -100.00 -73.00   3.69  192
 44  \w   -105.00 -79.00   0.50    0.05    -- -100.00 -70.00  29.13   52
 45  \w   -172.00-121.00   0.50    0.05    -- -100.00 -71.00  39.83  102
 46  \w   -158.00-119.00   0.50    0.05    -- -100.00 -64.00  91.79   78
 47  \w   -104.00 -78.00   0.50    0.05    -- -100.00 -71.00  39.83   52
 48  \w   -110.00 -81.00   0.50    0.05    -- -100.00 -61.00   0.00   58
 49  \w   -167.00-133.00   0.50    0.05    -- -100.00 -61.00  60.00   68
 50  \w   -156.00-130.00   0.50    0.05    -- -100.00 -61.00   0.00   52
 51  \w   -167.00 -84.00   0.50    0.05    -- -100.00 -63.00  84.68  166
 52  \w   -105.00 -80.00   0.50    0.05    -- -100.00 -64.00  91.79   50
 53  \w   -120.00 -83.00   0.50    0.05    -- -100.00 -61.00  60.00   74
 54  \w   -172.00 -81.00   0.50    0.05    -- -100.00 -61.00 120.00  182
 55  \w   -161.00-135.00   0.50    0.05    -- -100.00 -60.00  45.84   52
 56  \w   -112.00 -85.00   0.50    0.05    -- -100.00 -61.00 -30.00   54
 57  \w   -111.00 -86.00   0.50    0.05    -- -100.00 -51.00  23.04   50
 58  \w   -119.00 -85.00   0.50    0.05    -- -100.00 -45.00  30.00   68
 59  \w   -107.00 -82.00   0.50    0.05    -- -100.00 -60.00  45.84   50
 60  \w   -123.00 -25.00   0.50    0.05    --  -45.81 -15.00 153.00  196
 61  \w   -175.00 -79.00   0.50    0.05    -- -100.00 -15.00 153.00  192
;
_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      -0.0134263000
_diffrn_orient_matrix_UB_12      -0.0200388000
_diffrn_orient_matrix_UB_13      -0.1315999000
_diffrn_orient_matrix_UB_21      0.1389057000
_diffrn_orient_matrix_UB_22      -0.0324587000
_diffrn_orient_matrix_UB_23      0.0200683000
_diffrn_orient_matrix_UB_31      -0.0220920000
_diffrn_orient_matrix_UB_32      -0.1918879000
_diffrn_orient_matrix_UB_33      0.0102572000
_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  0.0323
_diffrn_reflns_av_unetI/netI     0.0205
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            20056
_diffrn_reflns_point_group_measured_fraction_full 0.968
_diffrn_reflns_point_group_measured_fraction_max 0.918
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         78.795
_diffrn_reflns_theta_min         3.830
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.539
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.61033
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.120a (Rigaku Oxford Diffraction, 2021)
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    1.173
_exptl_crystal_description       block
_exptl_crystal_F_000             388
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.107
_refine_diff_density_min         -0.174
_refine_diff_density_rms         0.039
_refine_ls_abs_structure_details
;
 Flack x determined using 1653 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.08(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     278
_refine_ls_number_reflns         4023
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.083
_refine_ls_R_factor_all          0.0317
_refine_ls_R_factor_gt           0.0312
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0473P)^2^+0.0957P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0800
_refine_ls_wR_factor_ref         0.0804
_reflns_Friedel_coverage         0.757
_reflns_Friedel_fraction_full    0.930
_reflns_Friedel_fraction_max     0.855
_reflns_number_gt                3942
_reflns_number_total             4023
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2gc04689j2.cif
_cod_data_source_block           chenzhh_b1_220427_auto
_cod_depositor_comments
'Adding full bibliography for 7246185--7246186.cif.'
_cod_database_code               7246186
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         CHNO
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     71.98
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Sof(C18A)=Sof(H18D)=Sof(H18E)=Sof(H18F)=Sof(C19A)=Sof(H19D)=Sof(H19E)=
 Sof(H19F)=Sof(C17A)=Sof(H17D)=Sof(H17E)=Sof(H17F)=1-FVAR(1)
 Sof(C17)=Sof(H17A)=Sof(H17B)=Sof(H17C)=Sof(C18)=Sof(H18A)=Sof(H18B)=Sof(H18C)=
 Sof(C19)=Sof(H19A)=Sof(H19B)=Sof(H19C)=FVAR(1)
3.a Ternary CH refined with riding coordinates:
 C21(H21)
3.b Secondary CH2 refined with riding coordinates:
 C26(H26A,H26B), C22(H22A,H22B), C25(H25A,H25B), C23(H23A,H23B), C24(H24A,H24B)
3.c Aromatic/amide H refined with riding coordinates:
 C5(H5), C11(H11), C14(H14), C12(H12), C20(H20), C13(H13), C8(H8), C6(H6),
 C7(H7)
3.d Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C18(H18A,H18B,H18C), C19(H19A,H19B,H19C), C18A(H18D,H18E,
 H18F), C19A(H19D,H19E,H19F), C17A(H17D,H17E,H17F)
;
_shelx_res_checksum              97059
_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 1.493
_oxdiff_exptl_absorpt_empirical_full_min 0.529