#------------------------------------------------------------------------------
#$Date: 2025-08-21 14:03:24 +0200 (Thu 21 de Aug de 2025) $
#$Revision: 301848 $
#$URL: svn://www.crystallography.net/cod/cif/7/02/57/7025756.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_7025756
loop_
_publ_author_name
'John, Alex'
'Shaikh, Mobin M.'
'Butcher, Ray J.'
'Ghosh, Prasenjit'
_publ_section_title
;
 Highly efficient palladium precatalysts of homoscorpionate bispyrazolyl
 ligands for the more challenging Suzuki-Miyaura cross-coupling of aryl
 chlorides.
;
_journal_issue                   31
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              7353
_journal_page_last               7363
_journal_paper_doi               10.1039/c003174g
_journal_volume                  39
_journal_year                    2010
_chemical_formula_moiety         'C19 H24 Cl2 N5 Pd'
_chemical_formula_sum            'C19 H24 Cl2 N5 Pd'
_chemical_formula_weight         499.73
_space_group_IT_number           62
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2n 2ac'
_symmetry_space_group_name_H-M   'P c m n'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.1966(2)
_cell_length_b                   13.6939(3)
_cell_length_c                   18.0046(4)
_cell_measurement_reflns_used    8677
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      32.4887
_cell_measurement_theta_min      2.9721
_cell_volume                     2020.90(8)
_computing_cell_refinement
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.31.7 (release 18-10-2006 CrysAlis171 .NET)
(compiled Oct 18 2006,16:28:17)
;
_computing_data_collection
;
CrysAlis CCD, Oxford Diffraction Ltd.,
Version 1.171.31.7 (release 18-10-2006 CrysAlis171 .NET)
(compiled Oct 18 2006,16:28:17)
;
_computing_data_reduction
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.31.7 (release 18-10-2006 CrysAlis171 .NET)
(compiled Oct 18 2006,16:28:17)
;
_computing_molecular_graphics    'SHELXLTL (Sheldrick, 2008)'
_computing_publication_material  SHELXLTL
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      123(2)
_diffrn_detector_area_resol_mean 15.9948
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.940
_diffrn_measurement_device_type  'Oxford Diffraction Xcaliber'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0396
_diffrn_reflns_av_sigmaI/netI    0.0427
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            19997
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         32.58
_diffrn_reflns_theta_min         2.98
_exptl_absorpt_coefficient_mu    1.197
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.94097
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.31.7 (release 18-10-2006 CrysAlis171 .NET)
(compiled Oct 18 2006,16:28:17)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            orange-yellow
_exptl_crystal_density_diffrn    1.642
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1012
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.729
_refine_diff_density_min         -0.626
_refine_diff_density_rms         0.090
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     138
_refine_ls_number_reflns         3588
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0435
_refine_ls_R_factor_gt           0.0275
_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/[σ²(Fo²)+(0.0358P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0652
_refine_ls_wR_factor_ref         0.0686
_reflns_number_gt                2761
_reflns_number_total             3588
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            c003174g.txt
_cod_data_source_block           pg100
_cod_database_code               7025756
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y+1/2, z+1/2'
'x+1/2, -y, -z+1/2'
'-x, y+1/2, -z'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'-x-1/2, y, z-1/2'
'x, -y-1/2, 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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
Pd1 Pd 0.16196(2) 0.7500 0.277075(10) 0.01510(6) Uani 1 2 d S
Cl1 Cl 0.18518(6) 0.87088(3) 0.36405(2) 0.02213(10) Uani 1 1 d .
N1 N 0.13354(18) 0.64491(12) 0.19927(8) 0.0175(3) Uani 1 1 d .
N2 N 0.25005(19) 0.61940(11) 0.14892(8) 0.0181(3) Uani 1 1 d .
N3 N 0.4473(3) 0.7500 0.11809(12) 0.0229(5) Uani 1 2 d S
C1 C -0.1465(2) 0.59542(16) 0.23436(11) 0.0247(4) Uani 1 1 d .
H1A H -0.1177 0.5893 0.2870 0.037 Uiso 1 1 calc R
H1B H -0.2224 0.5431 0.2207 0.037 Uiso 1 1 calc R
H1C H -0.1984 0.6589 0.2258 0.037 Uiso 1 1 calc R
C2 C 0.0046(2) 0.58771(14) 0.18802(10) 0.0199(4) Uani 1 1 d .
C3 C 0.0387(2) 0.52430(14) 0.12922(10) 0.0233(4) Uani 1 1 d .
H3A H -0.0323 0.4761 0.1093 0.028 Uiso 1 1 calc R
C4 C 0.1938(2) 0.54497(14) 0.10583(10) 0.0213(4) Uani 1 1 d .
C5 C 0.2921(3) 0.49896(15) 0.04545(11) 0.0291(5) Uani 1 1 d .
H5A H 0.3943 0.4737 0.0661 0.044 Uiso 1 1 calc R
H5B H 0.3165 0.5478 0.0073 0.044 Uiso 1 1 calc R
H5C H 0.2300 0.4452 0.0233 0.044 Uiso 1 1 calc R
C6 C 0.4162(2) 0.65981(14) 0.15440(10) 0.0214(4) Uani 1 1 d .
H6A H 0.4423 0.6681 0.2077 0.026 Uiso 1 1 calc R
H6B H 0.4930 0.6107 0.1342 0.026 Uiso 1 1 calc R
C7 C 0.4688(3) 0.7500 0.03721(14) 0.0230(6) Uani 1 2 d S
H7A H 0.4158 0.8066 0.0170 0.028 Uiso 0.50 1 d PR
C8 C 0.6460(3) 0.7500 0.01281(14) 0.0171(5) Uani 1 2 d S
C9 C 0.6805(3) 0.7500 -0.06341(15) 0.0232(6) Uani 1 2 d S
H9A H 0.5932 0.7500 -0.0981 0.028 Uiso 1 2 calc SR
C10 C 0.8410(3) 0.7500 -0.08906(16) 0.0270(6) Uani 1 2 d S
H10A H 0.8628 0.7500 -0.1409 0.032 Uiso 1 2 calc SR
C11 C 0.9704(3) 0.7500 -0.03785(16) 0.0268(6) Uani 1 2 d S
H11A H 1.0802 0.7500 -0.0547 0.032 Uiso 1 2 calc SR
C12 C 0.9360(3) 0.7500 0.03726(15) 0.0243(6) Uani 1 2 d S
H12A H 1.0229 0.7500 0.0722 0.029 Uiso 1 2 calc SR
C13 C 0.7757(3) 0.7500 0.06231(15) 0.0220(6) Uani 1 2 d S
H13A H 0.7546 0.7500 0.1142 0.026 Uiso 1 2 calc SR
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'
N N 0.0061 0.0033 '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'
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
N1 Pd1 N1 90.76(9) . 8_575
N1 Pd1 Cl1 177.99(4) . .
N1 Pd1 Cl1 88.21(5) 8_575 .
N1 Pd1 Cl1 88.21(5) . 8_575
N1 Pd1 Cl1 177.99(4) 8_575 8_575
Cl1 Pd1 Cl1 92.76(2) . 8_575
N1 Pd1 H6A 60.6 . .
N1 Pd1 H6A 94.0 8_575 .
Cl1 Pd1 H6A 121.2 . .
Cl1 Pd1 H6A 87.0 8_575 .
C2 N1 N2 107.71(15) . .
C2 N1 Pd1 128.02(12) . .
N2 N1 Pd1 124.25(12) . .
C4 N2 N1 109.50(15) . .
C4 N2 C6 129.23(15) . .
N1 N2 C6 120.46(14) . .
C6 N3 C6 120.8(2) 8_575 .
C6 N3 C7 118.58(11) 8_575 .
C6 N3 C7 118.58(11) . .
C2 C1 H1A 109.5 . .
C2 C1 H1B 109.5 . .
H1A C1 H1B 109.5 . .
C2 C1 H1C 109.5 . .
H1A C1 H1C 109.5 . .
H1B C1 H1C 109.5 . .
N1 C2 C3 108.82(16) . .
N1 C2 C1 122.05(16) . .
C3 C2 C1 129.13(18) . .
C4 C3 C2 106.86(17) . .
C4 C3 H3A 126.6 . .
C2 C3 H3A 126.6 . .
N2 C4 C3 107.10(16) . .
N2 C4 C5 123.25(18) . .
C3 C4 C5 129.65(19) . .
C4 C5 H5A 109.5 . .
C4 C5 H5B 109.5 . .
H5A C5 H5B 109.5 . .
C4 C5 H5C 109.5 . .
H5A C5 H5C 109.5 . .
H5B C5 H5C 109.5 . .
N3 C6 N2 117.48(17) . .
N3 C6 H6A 107.9 . .
N2 C6 H6A 107.9 . .
N3 C6 H6B 107.9 . .
N2 C6 H6B 107.9 . .
H6A C6 H6B 107.2 . .
N3 C7 C8 113.7(2) . .
N3 C7 H7A 108.8 . .
C8 C7 H7A 108.8 . .
C13 C8 C9 118.3(2) . .
C13 C8 C7 123.2(2) . .
C9 C8 C7 118.5(2) . .
C10 C9 C8 121.0(3) . .
C10 C9 H9A 119.5 . .
C8 C9 H9A 119.5 . .
C9 C10 C11 119.7(3) . .
C9 C10 H10A 120.2 . .
C11 C10 H10A 120.2 . .
C12 C11 C10 119.2(3) . .
C12 C11 H11A 120.4 . .
C10 C11 H11A 120.4 . .
C11 C12 C13 120.7(3) . .
C11 C12 H12A 119.6 . .
C13 C12 H12A 119.6 . .
C8 C13 C12 121.1(2) . .
C8 C13 H13A 119.4 . .
C12 C13 H13A 119.4 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Pd1 N1 2.0217(15) .
Pd1 N1 2.0217(15) 8_575
Pd1 Cl1 2.2866(5) .
Pd1 Cl1 2.2866(5) 8_575
Pd1 H6A 2.8458 .
N1 C2 1.331(2) .
N1 N2 1.362(2) .
N2 C4 1.361(2) .
N2 C6 1.473(2) .
N3 C6 1.420(2) 8_575
N3 C6 1.420(2) .
N3 C7 1.467(3) .
C1 C2 1.497(2) .
C1 H1A 0.9800 .
C1 H1B 0.9800 .
C1 H1C 0.9800 .
C2 C3 1.397(3) .
C3 C4 1.369(3) .
C3 H3A 0.9500 .
C4 C5 1.493(3) .
C5 H5A 0.9800 .
C5 H5B 0.9800 .
C5 H5C 0.9800 .
C6 H6A 0.9900 .
C6 H6B 0.9900 .
C7 C8 1.517(3) .
C7 H7A 0.9601 .
C8 C13 1.388(4) .
C8 C9 1.401(4) .
C9 C10 1.395(4) .
C9 H9A 0.9500 .
C10 C11 1.405(4) .
C10 H10A 0.9500 .
C11 C12 1.381(4) .
C11 H11A 0.9500 .
C12 C13 1.389(4) .
C12 H12A 0.9500 .
C13 H13A 0.9500 .
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
_geom_torsion_site_symmetry_1
N1 Pd1 N1 C2 -105.74(15) 8_575
Cl1 Pd1 N1 C2 -46.2(14) .
Cl1 Pd1 N1 C2 72.52(16) 8_575
H6A Pd1 N1 C2 160.1 .
N1 Pd1 N1 N2 75.62(14) 8_575
Cl1 Pd1 N1 N2 135.1(12) .
Cl1 Pd1 N1 N2 -106.12(13) 8_575
H6A Pd1 N1 N2 -18.5 .
C2 N1 N2 C4 -0.3(2) .
Pd1 N1 N2 C4 178.56(12) .
C2 N1 N2 C6 -170.99(16) .
Pd1 N1 N2 C6 7.9(2) .
N2 N1 C2 C3 -0.1(2) .
Pd1 N1 C2 C3 -178.93(12) .
N2 N1 C2 C1 179.52(16) .
Pd1 N1 C2 C1 0.7(3) .
N1 C2 C3 C4 0.5(2) .
C1 C2 C3 C4 -179.11(19) .
N1 N2 C4 C3 0.6(2) .
C6 N2 C4 C3 170.22(17) .
N1 N2 C4 C5 -179.41(17) .
C6 N2 C4 C5 -9.8(3) .
C2 C3 C4 N2 -0.7(2) .
C2 C3 C4 C5 179.4(2) .
C6 N3 C6 N2 86.6(3) 8_575
C7 N3 C6 N2 -76.9(2) .
C4 N2 C6 N3 103.3(2) .
N1 N2 C6 N3 -88.1(2) .
C6 N3 C7 C8 98.02(18) 8_575
C6 N3 C7 C8 -98.02(18) .
N3 C7 C8 C13 0.0 .
N3 C7 C8 C9 180.0 .
C13 C8 C9 C10 0.0 .
C7 C8 C9 C10 180.0 .
C8 C9 C10 C11 0.0 .
C9 C10 C11 C12 0.0 .
C10 C11 C12 C13 0.0 .
C9 C8 C13 C12 0.0 .
C7 C8 C13 C12 180.0 .
C11 C12 C13 C8 0.0 .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139161765
