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_7711727
_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         'C46 H37 F5 N2 O2 P2 Pd S'
_chemical_formula_sum            'C46 H37 F5 N2 O2 P2 Pd S'
_chemical_formula_weight         945.17
_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
_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                88.413(3)
_cell_angle_beta                 89.913(3)
_cell_angle_gamma                73.042(3)
_cell_formula_units_Z            4
_cell_length_a                   12.9823(5)
_cell_length_b                   14.2919(5)
_cell_length_c                   26.8298(11)
_cell_measurement_reflns_used    4905
_cell_measurement_temperature    298
_cell_measurement_theta_max      22.3410
_cell_measurement_theta_min      2.0130
_cell_volume                     4759.7(3)
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_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      298.0
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4757
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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    -79.00  18.00   1.00   44.96    --  -10.64 -57.00  90.00   97
  2  \w    -77.00  22.00   1.00   44.96    --  -10.64 -77.00 -30.00   99
  3  \w    -33.00  62.00   1.00   44.96    --  -10.64  57.00-120.00   95
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0232979000
_diffrn_orient_matrix_UB_12      -0.0423951000
_diffrn_orient_matrix_UB_13      0.0151242000
_diffrn_orient_matrix_UB_21      0.0120073000
_diffrn_orient_matrix_UB_22      -0.0285133000
_diffrn_orient_matrix_UB_23      -0.0216361000
_diffrn_orient_matrix_UB_31      0.0507528000
_diffrn_orient_matrix_UB_32      0.0091634000
_diffrn_orient_matrix_UB_33      -0.0016199000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0675
_diffrn_reflns_av_unetI/netI     0.1451
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            32504
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.027
_diffrn_reflns_theta_max         25.027
_diffrn_reflns_theta_min         1.692
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.557
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.97181
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear yellowish yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.319
_exptl_crystal_description       prism
_exptl_crystal_F_000             1920
_exptl_crystal_size_max          0.176
_exptl_crystal_size_mid          0.134
_exptl_crystal_size_min          0.079
_refine_diff_density_max         0.473
_refine_diff_density_min         -0.329
_refine_diff_density_rms         0.069
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.946
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1065
_refine_ls_number_reflns         16805
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.946
_refine_ls_R_factor_all          0.1515
_refine_ls_R_factor_gt           0.0646
_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^)+(0.0293P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0967
_refine_ls_wR_factor_ref         0.1261
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7964
_reflns_number_total             16805
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2dt03251a2.cif
_cod_data_source_block           fv539
_cod_original_cell_volume        4759.6(3)
_cod_database_code               7711727
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C46 H37 F5 N2 O2 P2 Pd S'
_chemical_oxdiff_usercomment     Yellow
_reflns_odcompleteness_completeness 86.27
_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:
 C016(H01A,H01B), C01B(H01H,H01K), C01H(H01E,H01F), C01S(H01S,H01T)
2.b Aromatic/amide H refined with riding coordinates:
 C00L(H00L), C00R(H00R), C010(H010), C017(H017), C018(H018), C019(H019),
 C01A(H01C), C01C(H01L), C01D(H01D), C01G(H01G), C01I(H01I), C01J(H01J),
 C01K(H01O), C01L(H01P), C01M(H01M), C01N(H01N), C01Q(H01Q), C01R(H01R),
 C01T(H01V), C01U(H01U), C01W(H01W), C01X(H01X), C01Z(H01Z), C020(H020),
 C021(H021), C023(H023), C024(H024), C025(H025), C026(H026), C027(H027),
 C028(H028), C02B(H02E), C02C(H02C), C02D(H02G), C02E(H02H), C02F(H02F),
 C02G(H02I), C02H(H02J), C02J(H02L), C02K(H02K), C02L(H02N), C02M(H02M),
 C02O(H02O), C02P(H02P), C02R(H02R), C02S(H02S), C02T(H02T), C02V(H02V),
 C02X(H02X), C02Y(H02Y), C030(H030), C031(H031), C032(H032), C034(H034),
 C035(H035), C036(H036), C037(H037), C038(H038), C039(H039), C03A(H03D)
2.c Idealised Me refined as rotating group:
 C02I(H02A,H02B,H02D), C033(H03A,H03B,H03C)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              40953
_shelx_hkl_checksum              3984
_shelx_fab_checksum              99089
_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 1.116
_oxdiff_exptl_absorpt_empirical_full_min 0.931