#------------------------------------------------------------------------------
#$Date: 2025-08-21 14:03:24 +0200 (Thu 21 de Aug de 2025) $
#$Revision: 301848 $
#$URL: svn://www.crystallography.net/cod/cif/7/02/06/7020602.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_7020602
loop_
_publ_author_name
'Tang, Fengzhi'
'Qu, Fengrui'
'Khusnutdinova, Julia R.'
'Rath, Nigam P.'
'Mirica, Liviu M.'
_publ_section_title
;
 Structural and reactivity comparison of analogous organometallic Pd(iii)
 and Pd(iv) complexes.
;
_journal_issue                   46
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              14046
_journal_page_last               14050
_journal_paper_doi               10.1039/c2dt32127k
_journal_volume                  41
_journal_year                    2012
_chemical_formula_moiety         'C17 H23 Cl N4 Pd, Cl O4, C2 H3 N'
_chemical_formula_sum            'C19 H26 Cl2 N5 O4 Pd'
_chemical_formula_weight         565.75
_space_group_crystal_system      orthorhombic
_space_group_IT_number           62
_space_group_name_Hall           '-P 2ac 2n'
_space_group_name_H-M_alt        'P n m a'
_symmetry_space_group_name_Hall  '-P 2ac 2n'
_symmetry_space_group_name_H-M   'P n m a'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2012
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.6407(8)
_cell_length_b                   9.5515(5)
_cell_length_c                   17.0852(8)
_cell_measurement_reflns_used    9871
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      32.75
_cell_measurement_theta_min      2.44
_cell_volume                     2226.0(2)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2012 (Sheldrick, 2012)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0453
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            41610
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         32.752
_diffrn_reflns_theta_min         1.910
_exptl_absorpt_coefficient_mu    1.110
_exptl_absorpt_correction_T_max  0.8619
_exptl_absorpt_correction_T_min  0.7946
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'sadabs v2008/1'
_exptl_crystal_colour            purple
_exptl_crystal_density_diffrn    1.688
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rectangular
_exptl_crystal_F_000             1148
_exptl_crystal_size_max          0.217
_exptl_crystal_size_mid          0.153
_exptl_crystal_size_min          0.138
_refine_diff_density_max         0.675
_refine_diff_density_min         -1.368
_refine_diff_density_rms         0.120
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.272
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     167
_refine_ls_number_reflns         4309
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.272
_refine_ls_R_factor_all          0.0469
_refine_ls_R_factor_gt           0.0399
_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/[σ²(Fo²)+(0.0103P)²+7.1000P]
where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0869
_refine_ls_wR_factor_ref         0.0892
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3838
_reflns_number_total             4309
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c2dt32127k.txt
_cod_data_source_block           l26410
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'no' was changed to '?' - the
value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_database_code               7020602
#BEGIN Tags that were not found in dictionaries:
_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_min   0.795
_shelx_estimated_absorpt_t_max   0.862
_diffrn_reflns_sigmai/neti       0.0252
#END Tags that were not found in dictionaries
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z'
'x+1/2, -y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z'
'-x-1/2, y-1/2, z-1/2'
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
_atom_site_disorder_assembly
_atom_site_disorder_group
Pd1 Pd 0.684310(18) 0.2500 0.538844(15) 0.01051(6) Uani 1 2 d SD . .
Cl1 Cl 0.6103(2) 0.0852(4) 0.4562(2) 0.0203(4) Uani 0.5 1 d PD A 1
C1 C 0.6320(9) 0.0980(16) 0.4679(8) 0.021(2) Uani 0.5 1 d PD A 2
H1A H 0.6739 0.0904 0.4215 0.031 Uiso 0.5 1 calc PRD A 2
H1B H 0.5651 0.1214 0.4518 0.031 Uiso 0.5 1 calc PRD A 2
H1C H 0.6318 0.0086 0.4960 0.031 Uiso 0.5 1 calc PRD A 2
N1 N 0.74995(15) 0.1075(2) 0.61515(12) 0.0123(4) Uani 1 1 d D A .
N3 N 0.8433(2) 0.2500 0.49377(17) 0.0140(5) Uani 1 2 d SD A .
N4 N 0.5751(2) 0.2500 0.64437(18) 0.0131(5) Uani 1 2 d SD A .
C2 C 0.70546(17) 0.0804(3) 0.68328(15) 0.0155(4) Uani 1 1 d D . .
C3 C 0.7550(2) 0.0123(3) 0.74288(17) 0.0207(5) Uani 1 1 d D A .
H3A H 0.7234 -0.0065 0.7913 0.025 Uiso 1 1 calc RD . .
C4 C 0.8515(2) -0.0279(3) 0.73057(17) 0.0205(5) Uani 1 1 d D . .
H4A H 0.8858 -0.0790 0.7697 0.025 Uiso 1 1 calc RD A .
C5 C 0.89753(19) 0.0067(3) 0.66110(16) 0.0182(5) Uani 1 1 d D A .
H5A H 0.9642 -0.0178 0.6526 0.022 Uiso 1 1 calc RD . .
C6 C 0.84503(18) 0.0775(3) 0.60414(15) 0.0143(4) Uani 1 1 d D . .
C7 C 0.88690(19) 0.1199(3) 0.52639(15) 0.0190(5) Uani 1 1 d D A .
H7A H 0.9585 0.1336 0.5322 0.023 Uiso 1 1 calc RD . .
H7B H 0.8766 0.0427 0.4886 0.023 Uiso 1 1 calc RD . .
C8 C 0.59879(18) 0.1212(3) 0.68829(17) 0.0188(5) Uani 1 1 d D A .
H8A H 0.5583 0.0434 0.6678 0.023 Uiso 1 1 calc RD . .
H8B H 0.5811 0.1350 0.7440 0.023 Uiso 1 1 calc RD . .
C9 C 0.8552(3) 0.2500 0.4083(2) 0.0218(8) Uani 1 2 d SD . .
H9A H 0.9238 0.2500 0.3957 0.033 Uiso 1 2 d SRD A .
H9B H 0.8249 0.1679 0.3867 0.033 Uiso 1 1 d RD . .
C10 C 0.4696(3) 0.2500 0.6250(2) 0.0179(7) Uani 1 2 d SD . .
H10A H 0.4311 0.2500 0.6721 0.027 Uiso 1 2 d SRD A .
H10B H 0.4546 0.3321 0.5949 0.027 Uiso 1 1 d RD . .
Cl2 Cl 0.84160(6) 0.7500 0.42400(5) 0.02066(18) Uani 1 2 d SD . .
O1 O 0.8679(2) 0.7500 0.50550(18) 0.0311(7) Uani 1 2 d SD . .
O2 O 0.7381(2) 0.7500 0.4150(2) 0.0435(10) Uani 1 2 d SD . .
O3 O 0.88280(18) 0.8722(3) 0.38712(13) 0.0327(5) Uani 1 1 d D . .
N1S N 0.4456(3) 0.2500 0.2763(2) 0.0290(8) Uani 1 2 d SD . .
C1S C 0.4088(3) 0.2500 0.3364(3) 0.0217(8) Uani 1 2 d SD . .
C2S C 0.3612(4) 0.2500 0.4121(3) 0.0301(10) Uani 1 2 d SD . .
H2S1 H 0.2922 0.2764 0.4058 0.045 Uiso 0.5 1 calc PRD B -1
H2S2 H 0.3938 0.3174 0.4466 0.045 Uiso 0.5 1 calc PRD B -1
H2S3 H 0.3652 0.1562 0.4351 0.045 Uiso 0.5 1 calc PRD B -1
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'
O O 0.0106 0.0060 '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
C1 Pd1 C1 91.8(9) 7_565 .
C1 Pd1 N1 174.0(4) 7_565 .
C1 Pd1 N1 93.3(5) . .
C1 Pd1 N1 93.3(5) 7_565 7_565
C1 Pd1 N1 174.0(4) . 7_565
N1 Pd1 N1 81.42(11) . 7_565
C1 Pd1 N3 97.6(4) 7_565 .
C1 Pd1 N3 97.6(4) . .
N1 Pd1 N3 78.74(8) . .
N1 Pd1 N3 78.74(8) 7_565 .
C1 Pd1 N4 103.8(4) 7_565 .
C1 Pd1 N4 103.8(4) . .
N1 Pd1 N4 77.97(8) . .
N1 Pd1 N4 77.97(8) 7_565 .
N3 Pd1 N4 149.12(10) . .
N1 Pd1 Cl1 97.09(11) . .
N1 Pd1 Cl1 178.32(11) 7_565 .
N3 Pd1 Cl1 101.78(10) . .
N4 Pd1 Cl1 100.98(11) . .
N1 Pd1 Cl1 178.32(11) . 7_565
N1 Pd1 Cl1 97.09(11) 7_565 7_565
N3 Pd1 Cl1 101.78(10) . 7_565
N4 Pd1 Cl1 100.98(11) . 7_565
Cl1 Pd1 Cl1 84.38(18) . 7_565
Pd1 C1 H1A 109.5 . .
Pd1 C1 H1B 109.5 . .
H1A C1 H1B 109.5 . .
Pd1 C1 H1C 109.5 . .
H1A C1 H1C 109.5 . .
H1B C1 H1C 109.5 . .
C2 N1 C6 121.3(2) . .
C2 N1 Pd1 118.39(16) . .
C6 N1 Pd1 117.81(17) . .
C9 N3 C7 109.17(18) . 7_565
C9 N3 C7 109.17(18) . .
C7 N3 C7 113.5(3) 7_565 .
C9 N3 Pd1 115.9(2) . .
C7 N3 Pd1 104.58(16) 7_565 .
C7 N3 Pd1 104.58(16) . .
C8 N4 C8 112.8(3) . 7_565
C8 N4 C10 109.08(18) . .
C8 N4 C10 109.08(18) 7_565 .
C8 N4 Pd1 104.61(16) . .
C8 N4 Pd1 104.61(16) 7_565 .
C10 N4 Pd1 116.7(2) . .
N1 C2 C3 120.7(2) . .
N1 C2 C8 115.9(2) . .
C3 C2 C8 123.4(2) . .
C2 C3 C4 118.8(3) . .
C2 C3 H3A 120.6 . .
C4 C3 H3A 120.6 . .
C5 C4 C3 119.6(2) . .
C5 C4 H4A 120.2 . .
C3 C4 H4A 120.2 . .
C4 C5 C6 119.0(2) . .
C4 C5 H5A 120.5 . .
C6 C5 H5A 120.5 . .
N1 C6 C5 120.4(2) . .
N1 C6 C7 115.7(2) . .
C5 C6 C7 123.8(2) . .
N3 C7 C6 113.9(2) . .
N3 C7 H7A 108.8 . .
C6 C7 H7A 108.8 . .
N3 C7 H7B 108.8 . .
C6 C7 H7B 108.8 . .
H7A C7 H7B 107.7 . .
N4 C8 C2 113.4(2) . .
N4 C8 H8A 108.9 . .
C2 C8 H8A 108.9 . .
N4 C8 H8B 108.9 . .
C2 C8 H8B 108.9 . .
H8A C8 H8B 107.7 . .
N3 C9 H9A 109.3 . .
N3 C9 H9B 109.6 . .
H9A C9 H9B 109.5 . .
N4 C10 H10A 110.2 . .
N4 C10 H10B 109.1 . .
H10A C10 H10B 109.5 . .
O2 Cl2 O1 110.7(2) . .
O2 Cl2 O3 109.90(13) . 7_575
O1 Cl2 O3 109.05(12) . 7_575
O2 Cl2 O3 109.90(13) . .
O1 Cl2 O3 109.05(12) . .
O3 Cl2 O3 108.2(2) 7_575 .
N1S C1S C2S 179.5(5) . .
C1S C2S H2S1 109.5 . .
C1S C2S H2S2 109.5 . .
H2S1 C2S H2S2 109.5 . .
C1S C2S H2S3 109.5 . .
H2S1 C2S H2S3 109.5 . .
H2S2 C2S H2S3 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Pd1 C1 2.021(11) 7_565
Pd1 C1 2.021(11) .
Pd1 N1 2.086(2) .
Pd1 N1 2.087(2) 7_565
Pd1 N3 2.301(3) .
Pd1 N4 2.339(3) .
Pd1 Cl1 2.343(3) .
Pd1 Cl1 2.343(3) 7_565
C1 H1A 0.9800 .
C1 H1B 0.9800 .
C1 H1C 0.9800 .
N1 C2 1.338(3) .
N1 C6 1.342(3) .
N3 C9 1.468(5) .
N3 C7 1.486(3) 7_565
N3 C7 1.486(3) .
N4 C8 1.477(3) .
N4 C8 1.477(3) 7_565
N4 C10 1.477(4) .
C2 C3 1.384(4) .
C2 C8 1.509(3) .
C3 C4 1.388(4) .
C3 H3A 0.9500 .
C4 C5 1.383(4) .
C4 H4A 0.9500 .
C5 C6 1.385(4) .
C5 H5A 0.9500 .
C6 C7 1.502(4) .
C7 H7A 0.9900 .
C7 H7B 0.9900 .
C8 H8A 0.9900 .
C8 H8B 0.9900 .
C9 H9A 0.9602 .
C9 H9B 0.9600 .
C10 H10A 0.9601 .
C10 H10B 0.9599 .
Cl2 O2 1.420(3) .
Cl2 O1 1.438(3) .
Cl2 O3 1.440(3) 7_575
Cl2 O3 1.440(3) .
N1S C1S 1.143(6) .
C1S C2S 1.448(6) .
C2S H2S1 0.9800 .
C2S H2S2 0.9800 .
C2S H2S3 0.9800 .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C7 H7A O3 0.99 2.57 3.473(4) 152.0 5_766
C7 H7B O3 0.99 2.38 3.356(4) 168.4 1_545
C8 H8B O3 0.99 2.50 3.407(4) 152.9 2_665
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
C6 N1 C2 C3 -4.0(4) .
Pd1 N1 C2 C3 -165.6(2) .
C6 N1 C2 C8 179.1(2) .
Pd1 N1 C2 C8 17.6(3) .
N1 C2 C3 C4 -0.3(4) .
C8 C2 C3 C4 176.2(3) .
C2 C3 C4 C5 3.2(4) .
C3 C4 C5 C6 -1.9(4) .
C2 N1 C6 C5 5.4(4) .
Pd1 N1 C6 C5 167.1(2) .
C2 N1 C6 C7 -177.1(2) .
Pd1 N1 C6 C7 -15.4(3) .
C4 C5 C6 N1 -2.4(4) .
C4 C5 C6 C7 -179.7(3) .
C9 N3 C7 C6 -155.9(3) .
C7 N3 C7 C6 82.1(3) 7_565
Pd1 N3 C7 C6 -31.3(3) .
N1 C6 C7 N3 33.2(3) .
C5 C6 C7 N3 -149.4(3) .
C8 N4 C8 C2 -81.8(3) 7_565
C10 N4 C8 C2 156.8(3) .
Pd1 N4 C8 C2 31.4(3) .
N1 C2 C8 N4 -34.8(3) .
C3 C2 C8 N4 148.5(3) .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139159060
