#------------------------------------------------------------------------------
#$Date: 2018-04-13 04:43:22 +0300 (Fri, 13 Apr 2018) $
#$Revision: 207330 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/04/7230470.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7230470
loop_
_publ_author_name
'Ocansey, Edward'
'Darkwa, James'
'Makhubela, Banothile C. E.'
_publ_section_title
;
 Synthesis, characterization and evaluation of bulky
 bis(pyrazolyl)palladium complexes in Suzuki--Miyaura cross-coupling
 reactions
;
_journal_issue                   25
_journal_name_full               'RSC Advances'
_journal_page_first              13826
_journal_paper_doi               10.1039/C8RA01430B
_journal_volume                  8
_journal_year                    2018
_chemical_formula_moiety         'C22 H18 Cl N2 Pd0.5'
_chemical_formula_sum            'C22 H18 Cl N2 Pd0.5'
_chemical_formula_weight         399.03
_chemical_name_systematic
'bis(2-benzyl-3,5-diphenyl-2,3-dihydro-1H-pyrazol-1-yl)palladium(IV) chloride'
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     dual
_audit_creation_date             2016-08-31
_audit_creation_method
;
Olex2 1.2
(compiled 2016.08.25 svn.r3337 for OlexSys, GUI svn.r5221)
;
_audit_update_record
;
2017-06-13 deposited with the CCDC.
2018-03-27 downloaded from the CCDC.
;
_cell_angle_alpha                102.123(2)
_cell_angle_beta                 98.442(2)
_cell_angle_gamma                94.970(2)
_cell_formula_units_Z            2
_cell_length_a                   6.7767(6)
_cell_length_b                   10.2586(9)
_cell_length_c                   13.5319(13)
_cell_measurement_reflns_used    6135
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.33
_cell_measurement_theta_min      2.28
_cell_volume                     903.05(14)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_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      100(2)
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART APEX2 area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0346
_diffrn_reflns_av_unetI/netI     0.0391
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            12765
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.357
_diffrn_reflns_theta_min         2.046
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.700
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6894
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0500 before and 0.0442 after correction.
The Ratio of minimum to maximum transmission is 0.9245.
The λ/2 correction factor is 0.00150.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.467
_exptl_crystal_description       block
_exptl_crystal_F_000             408
_exptl_crystal_size_max          0.364
_exptl_crystal_size_mid          0.125
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.457
_refine_diff_density_min         -0.311
_refine_diff_density_rms         0.079
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     304
_refine_ls_number_reflns         4497
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.082
_refine_ls_R_factor_all          0.0316
_refine_ls_R_factor_gt           0.0287
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0280P)²+0.4300P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0674
_refine_ls_wR_factor_ref         0.0687
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4175
_reflns_number_total             4497
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c8ra01430b2.cif
_cod_data_source_block           eo18a
_cod_original_formula_sum        'C22 H18 Cl N2 Pd0.50'
_cod_database_code               7230470
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_max   0.921
_shelx_estimated_absorpt_t_min   0.785
_olex2_refinement_description
;
;
_shelx_shelxl_version_number     2014/7
_olex2_exptl_crystal_mounting_method
'mounted on a MiTeGen DualThickness Micro-Mount, coated in a layer of Paratone oil'
_olex2_submission_original_sample_id EOI8A
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
Pd1 Pd 0.5000 0.5000 0.0000 0.01115(6) Uani 1 2 d S T P
Cl1 Cl 0.73553(6) 0.68220(4) 0.07234(3) 0.01664(10) Uani 1 1 d . . .
N2 N 0.3330(2) 0.56765(15) 0.19516(12) 0.0131(3) Uani 1 1 d . . .
N1 N 0.4455(2) 0.48586(15) 0.13993(12) 0.0127(3) Uani 1 1 d . . .
C22 C 0.2749(3) 0.61495(19) 0.46003(15) 0.0171(4) Uani 1 1 d . . .
H22 H 0.402(4) 0.600(2) 0.4759(18) 0.020(6) Uiso 1 1 d . . .
C6 C 0.3043(3) 0.81257(18) 0.23966(14) 0.0150(4) Uani 1 1 d . . .
C5 C 0.4987(3) 0.8591(2) 0.29212(16) 0.0192(4) Uani 1 1 d . . .
H5 H 0.595(4) 0.807(3) 0.2804(19) 0.028(6) Uiso 1 1 d . . .
C18 C -0.0138(3) 0.6094(2) 0.33138(16) 0.0184(4) Uani 1 1 d . . .
H18 H -0.078(3) 0.587(2) 0.2614(19) 0.021(6) Uiso 1 1 d . . .
C21 C 0.1668(3) 0.6650(2) 0.53660(16) 0.0205(4) Uani 1 1 d . . .
H21 H 0.224(4) 0.682(3) 0.603(2) 0.033(7) Uiso 1 1 d . . .
C12 C 0.7861(3) 0.3086(2) 0.11812(15) 0.0191(4) Uani 1 1 d . . .
H12 H 0.829(3) 0.392(2) 0.1175(16) 0.013(5) Uiso 1 1 d . . .
C7 C 0.2602(3) 0.68345(18) 0.15880(14) 0.0147(3) Uani 1 1 d . . .
H7A H 0.124(3) 0.663(2) 0.1328(17) 0.015(5) Uiso 1 1 d . . .
H7B H 0.323(3) 0.689(2) 0.1012(18) 0.018(6) Uiso 1 1 d . . .
C19 C -0.1213(3) 0.6583(2) 0.40821(17) 0.0217(4) Uani 1 1 d . . .
H19 H -0.248(4) 0.675(3) 0.390(2) 0.030(7) Uiso 1 1 d . . .
C1 C 0.1504(3) 0.8899(2) 0.26067(17) 0.0217(4) Uani 1 1 d . . .
H1 H 0.029(4) 0.863(2) 0.2270(18) 0.019(6) Uiso 1 1 d . . .
C16 C 0.5415(4) 0.1498(2) 0.15566(18) 0.0287(5) Uani 1 1 d . . .
H16 H 0.419(4) 0.129(3) 0.175(2) 0.034(7) Uiso 1 1 d . . .
C20 C -0.0319(3) 0.68541(19) 0.51009(16) 0.0211(4) Uani 1 1 d . . .
H20 H -0.105(4) 0.710(2) 0.5567(19) 0.028(6) Uiso 1 1 d . . .
C13 C 0.8999(4) 0.2053(2) 0.08767(18) 0.0279(5) Uani 1 1 d . . .
H13 H 1.021(4) 0.226(3) 0.067(2) 0.035(7) Uiso 1 1 d . . .
C4 C 0.5374(3) 0.9793(2) 0.36510(17) 0.0251(4) Uani 1 1 d . . .
H4 H 0.663(4) 1.009(3) 0.400(2) 0.036(7) Uiso 1 1 d . . .
C14 C 0.8340(4) 0.0756(2) 0.0906(2) 0.0378(6) Uani 1 1 d . . .
H14 H 0.909(4) 0.006(3) 0.072(2) 0.044(8) Uiso 1 1 d . . .
C3 C 0.3821(4) 1.0549(2) 0.38611(17) 0.0268(5) Uani 1 1 d . . .
H3 H 0.403(4) 1.136(3) 0.437(2) 0.036(7) Uiso 1 1 d . . .
C2 C 0.1891(4) 1.0105(2) 0.33322(19) 0.0281(5) Uani 1 1 d . . .
H2 H 0.083(4) 1.063(3) 0.348(2) 0.036(7) Uiso 1 1 d . . .
C15 C 0.6553(5) 0.0471(2) 0.1238(2) 0.0413(7) Uani 1 1 d . . .
H15 H 0.617(4) -0.034(3) 0.123(2) 0.032(7) Uiso 1 1 d . . .
C10 C 0.4853(3) 0.38862(18) 0.18966(14) 0.0143(3) Uani 1 1 d . . .
C8 C 0.3007(3) 0.52245(18) 0.27964(14) 0.0137(3) Uani 1 1 d . . .
C17 C 0.1858(3) 0.58587(17) 0.35731(14) 0.0142(3) Uani 1 1 d . . .
C11 C 0.6058(3) 0.28117(19) 0.15298(14) 0.0171(4) Uani 1 1 d . . .
C9 C 0.3969(3) 0.40849(18) 0.27776(14) 0.0154(4) Uani 1 1 d . . .
H9 H 0.399(3) 0.355(2) 0.3262(17) 0.018(6) Uiso 1 1 d . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Pd Pd -0.9988 1.0072 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
Cl1 Pd1 Cl1 180.0 2_665 .
N1 Pd1 Cl1 90.39(4) 2_665 2_665
N1 Pd1 Cl1 89.61(4) 2_665 .
N1 Pd1 Cl1 90.39(4) . .
N1 Pd1 Cl1 89.61(4) . 2_665
N1 Pd1 N1 180.0 2_665 .
N1 N2 C7 120.47(14) . .
C8 N2 N1 110.22(14) . .
C8 N2 C7 129.29(15) . .
N2 N1 Pd1 123.97(11) . .
C10 N1 Pd1 128.22(13) . .
C10 N1 N2 107.24(14) . .
C21 C22 H22 120.7(16) . .
C17 C22 H22 118.7(16) . .
C17 C22 C21 120.59(19) . .
C5 C6 C7 121.28(17) . .
C1 C6 C5 118.82(18) . .
C1 C6 C7 119.86(17) . .
C6 C5 H5 118.3(17) . .
C4 C5 C6 120.58(19) . .
C4 C5 H5 121.0(17) . .
C19 C18 H18 120.3(14) . .
C19 C18 C17 119.84(19) . .
C17 C18 H18 119.8(14) . .
C22 C21 H21 120.4(17) . .
C20 C21 C22 119.64(19) . .
C20 C21 H21 119.9(17) . .
C13 C12 H12 120.1(14) . .
C13 C12 C11 120.13(19) . .
C11 C12 H12 119.8(14) . .
N2 C7 C6 113.30(15) . .
N2 C7 H7A 108.5(13) . .
N2 C7 H7B 105.5(13) . .
C6 C7 H7A 112.0(14) . .
C6 C7 H7B 111.6(14) . .
H7A C7 H7B 105.4(18) . .
C18 C19 H19 118.9(17) . .
C20 C19 C18 120.43(19) . .
C20 C19 H19 120.7(17) . .
C6 C1 H1 119.5(16) . .
C2 C1 C6 120.7(2) . .
C2 C1 H1 119.9(16) . .
C15 C16 H16 119.2(16) . .
C11 C16 H16 120.6(16) . .
C11 C16 C15 120.2(2) . .
C21 C20 H20 121.0(17) . .
C19 C20 C21 120.25(19) . .
C19 C20 H20 118.6(17) . .
C12 C13 H13 118.6(17) . .
C14 C13 C12 120.0(2) . .
C14 C13 H13 121.4(17) . .
C5 C4 H4 120.5(18) . .
C5 C4 C3 120.0(2) . .
C3 C4 H4 119.5(18) . .
C13 C14 H14 120.9(17) . .
C13 C14 C15 120.3(2) . .
C15 C14 H14 118.8(17) . .
C4 C3 H3 122.0(17) . .
C2 C3 C4 119.8(2) . .
C2 C3 H3 118.2(17) . .
C1 C2 H2 120.7(17) . .
C3 C2 C1 120.1(2) . .
C3 C2 H2 119.2(16) . .
C16 C15 H15 121.6(18) . .
C14 C15 C16 120.2(2) . .
C14 C15 H15 118.2(18) . .
N1 C10 C11 122.90(16) . .
N1 C10 C9 109.13(16) . .
C9 C10 C11 127.97(16) . .
N2 C8 C17 125.41(16) . .
N2 C8 C9 106.75(16) . .
C9 C8 C17 127.84(16) . .
C22 C17 C18 119.23(17) . .
C22 C17 C8 118.56(17) . .
C18 C17 C8 122.08(17) . .
C12 C11 C10 121.68(17) . .
C16 C11 C12 119.16(18) . .
C16 C11 C10 119.14(17) . .
C10 C9 H9 127.2(14) . .
C8 C9 C10 106.65(15) . .
C8 C9 H9 126.2(14) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Pd1 Cl1 2.2924(4) .
Pd1 Cl1 2.2924(4) 2_665
Pd1 N1 2.0135(15) 2_665
Pd1 N1 2.0135(15) .
N2 N1 1.363(2) .
N2 C7 1.474(2) .
N2 C8 1.359(2) .
N1 C10 1.340(2) .
C22 H22 0.89(2) .
C22 C21 1.392(3) .
C22 C17 1.391(3) .
C6 C5 1.393(3) .
C6 C7 1.506(3) .
C6 C1 1.391(3) .
C5 H5 0.89(3) .
C5 C4 1.386(3) .
C18 H18 0.95(2) .
C18 C19 1.389(3) .
C18 C17 1.402(3) .
C21 H21 0.90(3) .
C21 C20 1.387(3) .
C12 H12 0.88(2) .
C12 C13 1.393(3) .
C12 C11 1.400(3) .
C7 H7A 0.93(2) .
C7 H7B 0.95(2) .
C19 H19 0.89(3) .
C19 C20 1.382(3) .
C1 H1 0.87(2) .
C1 C2 1.386(3) .
C16 H16 0.93(3) .
C16 C15 1.392(3) .
C16 C11 1.390(3) .
C20 H20 0.87(3) .
C13 H13 0.93(3) .
C13 C14 1.377(3) .
C4 H4 0.90(3) .
C4 C3 1.388(3) .
C14 H14 0.93(3) .
C14 C15 1.381(4) .
C3 H3 0.95(3) .
C3 C2 1.383(3) .
C2 H2 0.95(3) .
C15 H15 0.85(3) .
C10 C11 1.474(2) .
C10 C9 1.397(2) .
C8 C17 1.475(2) .
C8 C9 1.384(2) .
C9 H9 0.94(2) .
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
Pd1 N1 C10 C11 8.9(3)
Pd1 N1 C10 C9 -171.46(13)
N2 N1 C10 C11 -179.58(17)
N2 N1 C10 C9 0.1(2)
N2 C8 C17 C22 -127.92(19)
N2 C8 C17 C18 56.3(3)
N2 C8 C9 C10 -0.2(2)
N1 N2 C7 C6 -129.97(17)
N1 N2 C8 C17 179.78(16)
N1 N2 C8 C9 0.2(2)
N1 C10 C11 C12 45.2(3)
N1 C10 C11 C16 -136.6(2)
N1 C10 C9 C8 0.1(2)
C22 C21 C20 C19 -1.0(3)
C6 C5 C4 C3 -0.4(3)
C6 C1 C2 C3 -0.4(3)
C5 C6 C7 N2 53.8(2)
C5 C6 C1 C2 -0.6(3)
C5 C4 C3 C2 -0.7(3)
C18 C19 C20 C21 0.5(3)
C21 C22 C17 C18 1.0(3)
C21 C22 C17 C8 -174.90(17)
C12 C13 C14 C15 -0.1(4)
C7 N2 N1 Pd1 -6.5(2)
C7 N2 N1 C10 -178.50(16)
C7 N2 C8 C17 -2.1(3)
C7 N2 C8 C9 178.35(18)
C7 C6 C5 C4 178.89(17)
C7 C6 C1 C2 -178.55(18)
C19 C18 C17 C22 -1.5(3)
C19 C18 C17 C8 174.26(17)
C1 C6 C5 C4 1.0(3)
C1 C6 C7 N2 -128.27(18)
C13 C12 C11 C16 -0.7(3)
C13 C12 C11 C10 177.56(19)
C13 C14 C15 C16 -0.7(4)
C4 C3 C2 C1 1.0(3)
C15 C16 C11 C12 -0.1(4)
C15 C16 C11 C10 -178.4(2)
C8 N2 N1 Pd1 171.79(12)
C8 N2 N1 C10 -0.2(2)
C8 N2 C7 C6 52.1(2)
C17 C22 C21 C20 0.3(3)
C17 C18 C19 C20 0.7(3)
C17 C8 C9 C10 -179.72(18)
C11 C12 C13 C14 0.8(3)
C11 C16 C15 C14 0.8(4)
C11 C10 C9 C8 179.69(19)
C9 C10 C11 C12 -134.4(2)
C9 C10 C11 C16 43.8(3)
C9 C8 C17 C22 51.5(3)
C9 C8 C17 C18 -124.2(2)
