Chelating Palladium Complexes Containing Pyridine/pyrimidine Hydroxyalkyl Di-functionalized N-Heterocyclic Carbenes: Synthesis, Structure, and Catalytic Activity towards C-H Activation
Yang, Liangru; Yuan, Jinwei; Mao, Pu; Guo, Qi; RSC Adv.  (2015) –; doi:10.1039/C5RA21183B

data_7223468
_publ_section_title
;
 Chelating Palladium Complexes Containing Pyridine/pyrimidine Hydroxyalkyl
 Di-functionalized N-Heterocyclic Carbenes: Synthesis, Structure, and
 Catalytic Activity towards C-H Activation
;
_journal_name_full               'RSC Adv.'
_journal_paper_doi               10.1039/C5RA21183B
_journal_year                    2015
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C17 H17 Br2 N3 O Pd'
_chemical_formula_sum            'C17 H17 Br2 N3 O Pd'
_chemical_formula_weight         545.56
_chemical_name_systematic
;
 ? 
;
_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'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_date             2015-01-14
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.12 svn.r3133 for OlexSys, GUI svn.r4987)
;
_audit_update_record
;
2015-10-06 deposited with the CCDC.
2015-12-11 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 92.415(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   5.7083(3)
_cell_length_b                   12.8910(6)
_cell_length_c                   12.3640(6)
_cell_measurement_reflns_used    1890
_cell_measurement_temperature    291(2)
_cell_measurement_theta_max      72.1520
_cell_measurement_theta_min      7.7280
_cell_volume                     909.01(8)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_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      291.15
_diffrn_detector_area_resol_mean 16.2312
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details
;
  1 omega   -7.00   24.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -37.0000   90.0000 31

  2 omega  -59.00  -32.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  178.0000  -90.0000 27

  3 omega  -65.00  -37.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -37.0000   90.0000 28

  4 omega   50.00  128.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000   37.0000  -30.0000 78

  5 omega  -14.00   84.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000  -77.0000  -90.0000 98

  6 omega   29.00  120.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000   77.0000   30.0000 91

  7 omega   66.00   95.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000 -125.0000 -180.0000 29

  8 omega   67.00  108.00   1.0000   17.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -94.0000 -180.0000 41

  9 omega   43.00   75.00   1.0000   17.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -30.0000  -30.0000 32

 10 omega   45.00  134.00   1.0000   17.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -77.0000    0.0000 89

 11 omega   83.00  165.00   1.0000   17.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   30.0000  150.0000 82

 12 omega   74.00  102.00   1.0000   17.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -94.0000  -90.0000 28

 13 omega   43.00   87.00   1.0000   17.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -30.0000    0.0000 44

 14 omega   42.00   70.00   1.0000   17.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -30.0000   30.0000 28

 15 omega   44.00  104.00   1.0000   17.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -94.0000  -60.0000 60

 16 omega   51.00   77.00   1.0000   17.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -30.0000  -60.0000 26

 17 omega   49.00   97.00   1.0000   17.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -45.0000  -90.0000 48

 18 omega  -45.00   73.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   18.0000  107.0000 118

 19 omega   26.00  103.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000   77.0000 -150.0000 77
;
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0406969000
_diffrn_orient_matrix_UB_12      0.0281407000
_diffrn_orient_matrix_UB_13      0.1188308000
_diffrn_orient_matrix_UB_21      -0.2649461000
_diffrn_orient_matrix_UB_22      0.0103576000
_diffrn_orient_matrix_UB_23      -0.0269307000
_diffrn_orient_matrix_UB_31      -0.0336049000
_diffrn_orient_matrix_UB_32      -0.1156738000
_diffrn_orient_matrix_UB_33      0.0265554000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0613
_diffrn_reflns_av_unetI/netI     0.0736
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            3616
_diffrn_reflns_theta_full        67.07
_diffrn_reflns_theta_max         67.07
_diffrn_reflns_theta_min         3.58
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    13.457
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.26709
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.993
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       crystal
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.964
_refine_diff_density_min         -0.943
_refine_diff_density_rms         0.159
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.022(18)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         2353
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0590
_refine_ls_R_factor_gt           0.0562
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1030P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1457
_refine_ls_wR_factor_ref         0.1518
_reflns_number_gt                2194
_reflns_number_total             2353
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5ra21183b5.cif
_cod_data_source_block           20140109a
_cod_database_code               7223468
_chemical_oxdiff_formula         C1H1O1N1Pd1Cl1
_reflns_odcompleteness_completeness 99.71
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 O(H) groups
2.a Ternary CH refined with riding coordinates:
 C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C11(H11A,H11B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C7(H7), C8(H8), C13(H13), C14(H14), C15(H15),
 C16(H16), C17(H17)
2.d Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_olex2_submission_special_instructions 'No special instructions were received'