Palladium hydrazonato complexes and their role in the Pd-catalyzed cross-coupling reactions of hydrazones as carbene precursors
Villalba, Francisco; Albéniz, Ana C.; Dalton Transactions  (2022) –; doi:10.1039/D2DT03251A

data_7711725
_publ_section_title
;
 Palladium hydrazonato complexes and their role in the Pd-catalyzed
 cross-coupling reactions of hydrazones as carbene precursors
;
_journal_name_full               'Dalton Transactions'
_journal_paper_doi               10.1039/D2DT03251A
_journal_year                    2022
_chemical_formula_moiety         'C39 H31 F5 O2 P2 Pd S, C H2 Cl2'
_chemical_formula_sum            'C40 H33 Cl2 F5 O2 P2 Pd S'
_chemical_formula_weight         911.96
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2022-05-10
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2022-07-07 deposited with the CCDC.	2022-11-04 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 94.857(4)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   22.5623(15)
_cell_length_b                   11.1264(8)
_cell_length_c                   31.1487(13)
_cell_measurement_reflns_used    2618
_cell_measurement_temperature    298
_cell_measurement_theta_max      23.1140
_cell_measurement_theta_min      3.7660
_cell_volume                     7791.4(8)
_computing_cell_refinement       'CrysAlisPro 1.171.39.45g (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.45g (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.45g (Rigaku OD, 2018)'
_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      298
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4757
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.839
_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    -64.00  45.00   0.50   61.83    --   12.20 -77.00 -60.00  218
  2  \w    -10.00  85.00   0.50   61.83    --   12.20  77.00  30.00  190
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0225348000
_diffrn_orient_matrix_UB_12      0.0066814000
_diffrn_orient_matrix_UB_13      0.0171368000
_diffrn_orient_matrix_UB_21      -0.0217821000
_diffrn_orient_matrix_UB_22      -0.0038160000
_diffrn_orient_matrix_UB_23      0.0151000000
_diffrn_orient_matrix_UB_31      0.0036769000
_diffrn_orient_matrix_UB_32      -0.0632579000
_diffrn_orient_matrix_UB_33      0.0008724000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0635
_diffrn_reflns_av_unetI/netI     0.1199
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.839
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -43
_diffrn_reflns_number            20606
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.839
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         29.610
_diffrn_reflns_theta_min         3.314
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.808
_exptl_absorpt_correction_T_max  0.975
_exptl_absorpt_correction_T_min  0.913
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.45g (Rigaku Oxford Diffraction, 2018)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
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    1.555
_exptl_crystal_description       prism
_exptl_crystal_F_000             3680
_exptl_crystal_preparation       'diffusion at low temperature'
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.064
_refine_diff_density_max         1.388
_refine_diff_density_min         -0.906
_refine_diff_density_rms         0.113
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     464
_refine_ls_number_reflns         9211
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.016
_refine_ls_R_factor_all          0.1897
_refine_ls_R_factor_gt           0.0992
_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^)+(0.0912P)^2^+77.1164P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2189
_refine_ls_wR_factor_ref         0.2644
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4594
_reflns_number_total             9211
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2dt03251a2.cif
_cod_data_source_block           fvpxxx
_cod_database_code               7711725
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C39 H31 F5 O2 P2 Pd S'
_chemical_oxdiff_usercomment     Colurless
_shelx_estimated_absorpt_t_max   0.950
_shelx_estimated_absorpt_t_min   0.805
_reflns_odcompleteness_completeness 99.62
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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.a Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B), C14(H14A,H14B), C40(H40A,H40B)
2.b Aromatic/amide H refined with riding coordinates:
 C23(H23), C6(H6), C4(H4), C21(H21), C7(H7), C25(H25), C17(H17), C35(H35),
 C24(H24), C3(H3), C29(H29), C19(H19), C18(H18), C26(H26), C27(H27), C20(H20),
 C31(H31), C30(H30), C33(H33), C36(H36), C32(H32), C39(H39), C37(H37), C38(H38)
2.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
;
_shelx_res_checksum              33570
_shelx_hkl_checksum              7707
_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 1.468
_oxdiff_exptl_absorpt_empirical_full_min 0.771