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#$Date: 2025-08-21 01:01:10 +0300 (Thu, 21 Aug 2025) $
#$Revision: 301838 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/32/41/4324181.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_4324181
loop_
_publ_author_name
'Adam Duong'
'Thierry Maris'
'James D. Wuest'
_publ_section_title
;
 Using Pyridinyl-Substituted Diaminotriazines to Bind Pd(II) and Create
 Metallotectons for Engineering Hydrogen-Bonded Crystals
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              5605
_journal_page_last               5618
_journal_paper_doi               10.1021/ic2003047
_journal_volume                  50
_journal_year                    2011
_chemical_compound_source        'Synthesized by the authors. See text'
_chemical_formula_moiety         'C16 H16 Cl2 N12 Pd, C4 H8 O2, 2(C2 H6 O S)'
_chemical_formula_sum            'C24 H36 Cl2 N12 O4 Pd S2'
_chemical_formula_weight         798.07
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                105.458(6)
_cell_angle_beta                 96.393(6)
_cell_angle_gamma                97.755(7)
_cell_formula_units_Z            1
_cell_length_a                   6.1250(8)
_cell_length_b                   9.7568(13)
_cell_length_c                   15.6448(18)
_cell_measurement_reflns_used    6698
_cell_measurement_temperature    150
_cell_measurement_theta_max      67.23
_cell_measurement_theta_min      2.97
_cell_volume                     882.2(2)
_computing_cell_refinement       'SAINT V7.68A(Bruker AXS, )'
_computing_data_collection       'APEX2  (Bruker AXS, 1)'
_computing_data_reduction        'SAINT V7.68A(Bruker AXS, )'
_computing_molecular_graphics    'SHELXTL v6.12 (Bruker AXS, 2001)'
_computing_publication_material  'UdMX (Maris, 2004)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      150
_diffrn_detector_area_resol_mean 8.3
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_device_type  'Bruker Microstar'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  'Helios optics'
_diffrn_radiation_source         'Rotating Anode'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.047
_diffrn_reflns_av_sigmaI/netI    0.0404
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            12588
_diffrn_reflns_theta_full        68.00
_diffrn_reflns_theta_max         68.00
_diffrn_reflns_theta_min         2.97
_exptl_absorpt_coefficient_mu    7.152
_exptl_absorpt_correction_T_max  0.8069
_exptl_absorpt_correction_T_min  0.6052
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Sadabs (Sheldrick, 2008)'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.502
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             408
_exptl_crystal_size_max          0.09
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.03
_refine_diff_density_max         1.068
_refine_diff_density_min         -0.721
_refine_diff_density_rms         0.090
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     212
_refine_ls_number_reflns         3156
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0533
_refine_ls_R_factor_gt           0.0491
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0804P)²+1.1567P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1340
_refine_ls_wR_factor_ref         0.1377
_reflns_number_gt                2882
_reflns_number_total             3156
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            COD_Inorg_Chem_50_2011_5605_5618.cif
_cod_data_source_block           adam23
_cod_original_cell_volume        882.19(19)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               4324181
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Pd1 Pd 0.5000 0.5000 0.5000 0.0530(2) Uani 1 2 d S . .
Cl1 Cl 0.5094(2) 0.26124(13) 0.49555(8) 0.0665(3) Uani 1 1 d . . .
N1 N 0.3249(6) 0.5216(4) 0.6033(2) 0.0556(9) Uani 1 1 d . . .
C1 C 0.1190(8) 0.4444(5) 0.5936(3) 0.0594(12) Uani 1 1 d . . .
H1 H 0.0545 0.3797 0.5367 0.071 Uiso 1 1 calc R . .
C2 C 0.0003(8) 0.4569(5) 0.6641(3) 0.0557(11) Uani 1 1 d . . .
H2 H -0.1450 0.4021 0.6555 0.067 Uiso 1 1 calc R . .
C3 C 0.0930(7) 0.5492(4) 0.7471(3) 0.0458(9) Uani 1 1 d . . .
C4 C 0.3034(8) 0.6286(5) 0.7555(3) 0.0582(11) Uani 1 1 d . . .
H4 H 0.3720 0.6939 0.8117 0.070 Uiso 1 1 calc R . .
C5 C 0.4122(8) 0.6130(6) 0.6827(3) 0.0615(12) Uani 1 1 d . . .
H5 H 0.5553 0.6695 0.6893 0.074 Uiso 1 1 calc R . .
C6 C -0.0268(6) 0.5599(4) 0.8263(3) 0.0421(8) Uani 1 1 d . . .
N2 N -0.2224(6) 0.4739(4) 0.8116(2) 0.0468(8) Uani 1 1 d . . .
C7 C -0.3212(6) 0.4862(4) 0.8858(3) 0.0437(9) Uani 1 1 d . . .
N3 N -0.2352(5) 0.5760(4) 0.9674(2) 0.0438(7) Uani 1 1 d . . .
C8 C -0.0360(6) 0.6561(4) 0.9726(3) 0.0410(8) Uani 1 1 d . . .
N4 N 0.0765(6) 0.6535(4) 0.9027(2) 0.0458(8) Uani 1 1 d . . .
N5 N -0.5183(6) 0.4026(4) 0.8770(2) 0.0575(10) Uani 1 1 d . . .
H5A H -0.5875 0.4075 0.9239 0.069 Uiso 1 1 calc . . .
H5B H -0.5792 0.3426 0.8245 0.069 Uiso 1 1 calc . . .
N6 N 0.0575(6) 0.7472(4) 1.0518(2) 0.0494(8) Uani 1 1 d . . .
H6A H -0.0115 0.7534 1.0988 0.059 Uiso 1 1 calc . . .
H6B H 0.1884 0.8012 1.0573 0.059 Uiso 1 1 calc . . .
O2 O 0.4357(6) 1.0013(4) 1.0839(2) 0.0644(8) Uani 1 1 d . . .
C10 C 0.3515(9) 1.0877(6) 1.0320(4) 0.0673(13) Uani 1 1 d . . .
H10A H 0.4468 1.1842 1.0505 0.081 Uiso 1 1 calc R . .
H10B H 0.1990 1.1006 1.0438 0.081 Uiso 1 1 calc R . .
C11 C 0.6542(8) 0.9797(6) 1.0660(4) 0.0629(12) Uani 1 1 d . . .
H11A H 0.7101 0.9162 1.1002 0.075 Uiso 1 1 calc R . .
H11B H 0.7570 1.0735 1.0856 0.075 Uiso 1 1 calc R . .
S1 S 0.0181(4) 0.9111(3) 1.31209(15) 0.1034(11) Uani 0.835(8) 1 d P A 1
O3 O -0.1224(7) 0.8205(5) 1.2288(3) 0.0832(11) Uani 1 1 d . A 1
C12 C -0.002(3) 1.048(3) 1.3080(12) 0.293(14) Uani 1 1 d . A 1
H12A H -0.1548 1.0484 1.2824 0.439 Uiso 1 1 calc R A 1
H12B H 0.1017 1.0772 1.2702 0.439 Uiso 1 1 calc R A 1
H12C H 0.0339 1.1149 1.3686 0.439 Uiso 1 1 calc R A 1
C13 C 0.2969(15) 0.9233(10) 1.2983(7) 0.131(3) Uani 1 1 d . A 1
H13A H 0.3260 0.9792 1.2559 0.197 Uiso 1 1 calc R A 1
H13B H 0.3308 0.8262 1.2748 0.197 Uiso 1 1 calc R A 1
H13C H 0.3911 0.9715 1.3563 0.197 Uiso 1 1 calc R A 1
S1B S -0.035(5) 0.970(3) 1.401(2) 0.214(14) Uiso 0.165(8) 1 d P A 2
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Pd Pd 0.1215 3.9337 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
N1 PD1 N1 2_666 . 179.999(1) y
N1 PD1 CL1 2_666 . 89.80(12) y
N1 PD1 CL1 . . 90.20(12) y
N1 PD1 CL1 2_666 2_666 90.20(12) y
N1 PD1 CL1 . 2_666 89.80(12) y
CL1 PD1 CL1 . 2_666 180.00(6) y
C5 N1 C1 . . 118.7(4) y
C5 N1 PD1 . . 119.9(3) y
C1 N1 PD1 . . 121.4(3) y
N1 C1 C2 . . 121.7(4) y
N1 C1 H1 . . 119.2 ?
C2 C1 H1 . . 119.2 ?
C1 C2 C3 . . 119.7(4) y
C1 C2 H2 . . 120.2 ?
C3 C2 H2 . . 120.2 ?
C2 C3 C4 . . 117.8(4) y
C2 C3 C6 . . 121.1(4) y
C4 C3 C6 . . 121.1(4) y
C5 C4 C3 . . 119.9(4) y
C5 C4 H4 . . 120.1 ?
C3 C4 H4 . . 120.1 ?
N1 C5 C4 . . 122.3(4) y
N1 C5 H5 . . 118.9 ?
C4 C5 H5 . . 118.9 ?
N2 C6 N4 . . 127.9(3) y
N2 C6 C3 . . 116.0(3) y
N4 C6 C3 . . 116.0(3) y
C6 N2 C7 . . 113.5(3) y
N5 C7 N3 . . 117.8(3) y
N5 C7 N2 . . 117.4(4) y
N3 C7 N2 . . 124.8(4) y
C8 N3 C7 . . 115.3(3) y
N6 C8 N3 . . 118.0(3) y
N6 C8 N4 . . 117.1(3) y
N3 C8 N4 . . 124.8(4) y
C6 N4 C8 . . 113.6(3) y
C7 N5 H5A . . 120 ?
C7 N5 H5B . . 120 ?
H5A N5 H5B . . 120 ?
C8 N6 H6A . . 120 ?
C8 N6 H6B . . 120 ?
H6A N6 H6B . . 120 ?
C10 O2 C11 . . 109.7(4) y
O2 C10 C11 . 2_677 111.5(4) y
O2 C10 H10A . . 109.3 ?
C11 C10 H10A 2_677 . 109.3 ?
O2 C10 H10B . . 109.3 ?
C11 C10 H10B 2_677 . 109.3 ?
H10A C10 H10B . . 108 ?
O2 C11 C10 . 2_677 110.0(4) y
O2 C11 H11A . . 109.7 ?
C10 C11 H11A 2_677 . 109.7 ?
O2 C11 H11B . . 109.7 ?
C10 C11 H11B 2_677 . 109.7 ?
H11A C11 H11B . . 108.2 ?
C12 S1 O3 . . 102.2(7) y
C12 S1 C13 . . 96.1(8) y
O3 S1 C13 . . 109.7(4) y
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Pd1 N1 2_666 2.018(3) y
Pd1 N1 . 2.018(3) y
Pd1 Cl1 . 2.3207(13) y
Pd1 Cl1 2_666 2.3207(13) y
N1 C5 . 1.326(6) y
N1 C1 . 1.349(6) y
C1 C2 . 1.374(6) y
C1 H1 . 0.95 ?
C2 C3 . 1.377(6) y
C2 H2 . 0.95 ?
C3 C4 . 1.385(6) y
C3 C6 . 1.495(5) y
C4 C5 . 1.366(6) y
C4 H4 . 0.95 ?
C5 H5 . 0.95 ?
C6 N2 . 1.325(5) y
C6 N4 . 1.326(5) y
N2 C7 . 1.353(5) y
C7 N5 . 1.334(5) y
C7 N3 . 1.344(5) y
N3 C8 . 1.338(5) y
C8 N6 . 1.331(5) y
C8 N4 . 1.352(5) y
N5 H5a . 0.88 ?
N5 H5b . 0.88 ?
N6 H6a . 0.88 ?
N6 H6b . 0.88 ?
O2 C10 . 1.422(6) y
O2 C11 . 1.429(6) y
C10 C11 2_677 1.494(8) y
C10 H10a . 0.99 ?
C10 H10b . 0.99 ?
C11 C10 2_677 1.494(8) y
C11 H11a . 0.99 ?
C11 H11b . 0.99 ?
S1 C12 . 1.37(2) y
S1 O3 . 1.466(4) y
S1 C13 . 1.737(10) y
C12 H12a . 0.98 ?
C12 H12b . 0.98 ?
C12 H12c . 0.98 ?
C13 H13a . 0.98 ?
C13 H13b . 0.98 ?
C13 H13c . 0.98 ?
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
N5 H5A N3 0.88 2.1 2.980(5) 177.1 2_467
N5 H5B O3 0.88 2.18 2.881(5) 136.7 2_467
N6 H6A O3 0.88 2.18 3.038(5) 165.3 .
N6 H6B O2 0.88 2.22 3.049(5) 157.8 .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139135324
