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_7246185
_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         'C27 H27 N O'
_chemical_formula_sum            'C27 H27 N O'
_chemical_formula_weight         381.49
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_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                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.78370(10)
_cell_length_b                   31.1021(4)
_cell_length_c                   8.64470(10)
_cell_measurement_reflns_used    14797
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      78.9740
_cell_measurement_theta_min      2.7890
_cell_volume                     2092.79(5)
_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 0.979
_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     36.00 112.00   0.50    0.05    --  104.88-157.00   8.00  152
  2  \w     51.00  89.00   0.50    0.05    --   45.56-114.00  69.00   76
  3  \w     33.00  58.00   0.50    0.05    --  104.88 -61.00 -60.00   50
  4  \w     32.00  72.00   0.50    0.05    --  104.88 -61.00-150.00   80
  5  \w    -19.00  25.00   0.50    0.05    --   45.56 -19.00 -30.00   88
  6  \w     43.00 117.00   0.50    0.05    --   45.56  57.00 -90.00  148
  7  \w     94.00 177.00   0.50    0.05    --  104.88  16.00  56.00  166
  8  \w    -69.00 -43.00   0.50    0.05    -- -100.00  61.00 -90.00   52
  9  \w    -91.00 -52.00   0.50    0.05    -- -100.00  77.00-180.00   78
 10  \w   -106.00 -27.00   0.50    0.05    -- -100.00 114.00 160.00  158
 11  \w   -131.00 -99.00   0.50    0.05    -- -100.00 157.00  44.00   64
 12  \w    -24.00  28.00   0.50    0.05    --  -45.56  19.00 120.00  104
 13  \w     -7.00  23.00   0.50    0.05    --  -45.56  19.00-150.00   60
 14  \w   -172.00-122.00   0.50    0.05    -- -100.00 -15.00 150.00  100
 15  \w     41.00  67.00   0.50    0.05    --  112.25 -61.00-180.00   52
 16  \w     65.00 102.00   0.50    0.05    --  112.25 -94.00-150.00   74
 17  \w    117.00 178.00   0.50    0.05    --  112.25  45.00-150.00  122
 18  \w    133.00 163.00   0.50    0.05    --  112.25  77.00 -60.00   60
 19  \w     51.00 105.00   0.50    0.05    --  112.25 -94.00 150.00  108
 20  \w     41.00  86.00   0.50    0.05    --  112.25 -94.00 -30.00   90
 21  \w     40.00  66.00   0.50    0.05    --  112.25 -61.00  60.00   52
 22  \w     88.00 127.00   0.50    0.05    --  112.25  77.00 -60.00   78
 23  \w     40.00  65.00   0.50    0.05    --  112.25 -61.00  90.00   50
 24  \w     46.00  72.00   0.50    0.05    --  112.25 -61.00 150.00   52
 25  \w   -118.00 -21.00   0.50    0.05    --  -45.56 -77.00  60.00  194
 26  \w   -118.00 -21.00   0.50    0.05    --  -45.56 -77.00 150.00  194
 27  \w     21.00 118.00   0.50    0.05    --   45.56  77.00-150.00  194
 28  \w     18.00  95.00   0.50    0.05    --   45.56-125.00 150.00  154
 29  \w     28.00 118.00   0.50    0.05    --   45.56  57.00   0.00  180
 30  \w     96.00 170.00   0.50    0.05    --  112.25  30.00-180.00  148
 31  \w     40.00  73.00   0.50    0.05    --  112.25 -61.00 -30.00   66
;
_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      -0.0376371000
_diffrn_orient_matrix_UB_12      0.0205408000
_diffrn_orient_matrix_UB_13      0.1585890000
_diffrn_orient_matrix_UB_21      0.0209169000
_diffrn_orient_matrix_UB_22      -0.0441900000
_diffrn_orient_matrix_UB_23      0.0781794000
_diffrn_orient_matrix_UB_31      0.1932150000
_diffrn_orient_matrix_UB_32      0.0087796000
_diffrn_orient_matrix_UB_33      0.0225245000
_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  0.0570
_diffrn_reflns_av_unetI/netI     0.0323
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       39
_diffrn_reflns_limit_k_min       -38
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            20246
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.967
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         78.973
_diffrn_reflns_theta_min         2.842
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.558
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.22787
_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    1.211
_exptl_crystal_description       block
_exptl_crystal_F_000             816
_exptl_crystal_size_max          0.450
_exptl_crystal_size_mid          0.400
_exptl_crystal_size_min          0.300
_refine_diff_density_max         0.263
_refine_diff_density_min         -0.274
_refine_diff_density_rms         0.048
_refine_ls_abs_structure_details
;
 Flack x determined using 1655 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.04(19)
_refine_ls_extinction_coef       0.0029(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     268
_refine_ls_number_reflns         4366
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.0484
_refine_ls_R_factor_gt           0.0471
_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^)+(0.0587P)^2^+1.1068P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1222
_refine_ls_wR_factor_ref         0.1231
_reflns_Friedel_coverage         0.710
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.950
_reflns_number_gt                4200
_reflns_number_total             4366
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2gc04689j2.cif
_cod_data_source_block           chenzhh_a2_220427_auto
_cod_depositor_comments
'Adding full bibliography for 7246185--7246186.cif.'
_cod_database_code               7246185
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         CHNO
_reflns_odcompleteness_completeness 99.91
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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:
 C26(H26), C8(H8), C11(H11), C5(H5), C20(H20), C24(H24), C22(H22), C7(H7),
 C14(H14), C6(H6), C12(H12), C13(H13)
2.b Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C18(H18A,H18B,H18C), C19(H19A,H19B,H19C), C28(H28A,H28B,
 H28C), C27(H27A,H27B,H27C)
;
_shelx_res_checksum              30829
_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 3.133
_oxdiff_exptl_absorpt_empirical_full_min 0.440