(N-Heterocyclic Carbene)-Palladate Complexes in Anionic Mizoroki‒Heck Coupling Cycles: A Combined Experimental and Computational Study
Guest, Daniel; Menezes da Silva, Vitor H.; de Lima Batista, Ana P.; Roe, S. Mark; Braga, Ataualpa A. C.; Navarro, Oscar; Organometallics 34 (2015) 2463–; doi:10.1021/om5012038

data_4085326
_publ_section_title
;
 (N-Heterocyclic Carbene)-Palladate Complexes in Anionic Mizoroki--Heck
 Coupling Cycles: A Combined Experimental and Computational Study
;
_journal_issue                   11
_journal_name_full               Organometallics
_journal_page_first              2463
_journal_paper_doi               10.1021/om5012038
_journal_volume                  34
_journal_year                    2015
_chemical_formula_moiety         'C27 H38 Cl3 N2 Pd, C16 H36 N, H2 O'
_chemical_formula_sum            'C43 H76 Cl3 N3 O Pd'
_chemical_formula_weight         863.81
_chemical_name_systematic
;
 ?
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_audit_creation_date             2014-09-25
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2014.09.19 svn.r3010 for OlexSys, GUI svn.r4874)
;
_cell_angle_alpha                90
_cell_angle_beta                 94.780(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.6242(4)
_cell_length_b                   13.8197(3)
_cell_length_c                   20.6116(5)
_cell_measurement_reflns_used    10479
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      29.0970
_cell_measurement_theta_min      3.8270
_cell_volume                     4718.87(19)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_temperature      173.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1033
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.881
_diffrn_measurement_details
;
  1 omega  -30.00   51.00   1.0000   90.0000
omega____ theta____ kappa____ phi______ frames
    -      -16.1295   57.0000 -120.0000 81

  2 omega  -84.00   11.00   1.0000   90.0000
omega____ theta____ kappa____ phi______ frames
    -      -16.1295  -77.0000  120.0000 95

  3 omega  -31.00   45.00   1.0000   90.0000
omega____ theta____ kappa____ phi______ frames
    -      -16.1295   57.0000    0.0000 76

  4 omega  -63.00  -37.00   1.0000   90.0000
omega____ theta____ kappa____ phi______ frames
    -      -16.1295  178.0000  -30.0000 26

  5 omega  -77.00    1.00   1.0000   90.0000
omega____ theta____ kappa____ phi______ frames
    -      -16.1295  -57.0000 -120.0000 78

  6 omega  -35.00   -9.00   1.0000   90.0000
omega____ theta____ kappa____ phi______ frames
    -      -16.1295  -74.0000   25.0000 26

  7 omega   29.00   55.00   1.0000   90.0000
omega____ theta____ kappa____ phi______ frames
    -       16.7545  -99.0000 -120.0000 26
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0414370000
_diffrn_orient_matrix_UB_12      0.0119161000
_diffrn_orient_matrix_UB_13      -0.0004277000
_diffrn_orient_matrix_UB_21      -0.0089628000
_diffrn_orient_matrix_UB_22      0.0282552000
_diffrn_orient_matrix_UB_23      -0.0284183000
_diffrn_orient_matrix_UB_31      -0.0058259000
_diffrn_orient_matrix_UB_32      0.0411595000
_diffrn_orient_matrix_UB_33      0.0196417000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0475
_diffrn_reflns_av_unetI/netI     0.0520
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.881
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            40597
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.881
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         29.432
_diffrn_reflns_theta_min         3.314
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.596
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.78518
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'light yellow'
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.216
_exptl_crystal_description       plate
_exptl_crystal_F_000             1840
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.05
_refine_diff_density_max         1.017
_refine_diff_density_min         -0.472
_refine_diff_density_rms         0.069
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     500
_refine_ls_number_reflns         11493
_refine_ls_number_restraints     345
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.0649
_refine_ls_R_factor_gt           0.0401
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0436P)^2^+1.0710P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0890
_refine_ls_wR_factor_ref         0.0999
_reflns_Friedel_coverage         0.000
_reflns_number_gt                8553
_reflns_number_total             11493
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            om5012038_si_002.cif
_cod_data_source_block           dg_spirpdcl3tba_x2
_cod_depositor_comments          'Adding full bibliography for 4085326.cif.'
_cod_original_cell_volume        4718.9(2)
_cod_database_code               4085326
_shelxl_version_number           2013-4
_chemical_oxdiff_formula         'C50 H100 Cl3 Pd1'
_chemical_oxdiff_usercomment     'Thin plate to avoid twinning.'
_reflns_odcompleteness_completeness 99.70
_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, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 H1B-O1
 0.96 with sigma of 0.02
 H1A-O1
 0.96 with sigma of 0.02
 H1B-H1A
 1.57 with sigma of 0.04
3. Rigid body (RIGU) restrains
 Pd1, Cl2, Cl1, Cl3, C1, N1, N2, C2, C16, C3, C4, C21, C17, C5, C9, C25, C20,
 C22, C18, C6, C10, C13, C8, C27, C26, C19, C24, C23, C7, C12, C11, C15, C14
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 N3, C32, C28, C36, C40, C37, C41, C38, C42, C42A, C39, C43, C43A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4. Others
 Sof(H41C)=Sof(H41D)=Sof(C42A)=Sof(H42C)=Sof(H42D)=Sof(C43A)=Sof(H43D)=
 Sof(H43E)=Sof(H43F)=1-FVAR(1)
 Sof(H41A)=Sof(H41B)=Sof(C42)=Sof(H42A)=Sof(H42B)=Sof(C43)=Sof(H43A)=Sof(H43B)=
 Sof(H43C)=FVAR(1)
5.a Ternary CH refined with riding coordinates:
 C13(H13), C25(H25), C22(H22), C10(H10)
5.b Secondary CH2 refined with riding coordinates:
 C32(H32A,H32B), C38(H38A,H38B), C41(H41A,H41B), C41(H41C,H41D), C2(H2A,H2B),
 C28(H28A,H28B), C42(H42A,H42B), C36(H36A,H36B), C3(H3A,H3B), C40(H40A,H40B),
 C37(H37A,H37B), C42A(H42C,H42D), C33(H33A,H33B), C29(H29A,H29B), C34(H34A,
 H34B), C30(H30A,H30B)
5.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C18(H18), C8(H8), C20(H20), C19(H19)
5.d Idealised Me refined as rotating group:
 C27(H27A,H27B,H27C), C24(H24A,H24B,H24C), C15(H15A,H15B,H15C), C23(H23A,H23B,
 H23C), C12(H12A,H12B,H12C), C11(H11A,H11B,H11C), C26(H26A,H26B,H26C), C39(H39A,
 H39B,H39C), C43(H43A,H43B,H43C), C14(H14A,H14B,H14C), C43A(H43D,H43E,H43F),
 C35(H35A,H35B,H35C), C31(H31A,H31B,H31C)
;
_olex2_submission_special_instructions 'No special instructions were received'