#------------------------------------------------------------------------------
#$Date: 2026-03-04 23:07:56 +0100 (Wed 04 de Mar de 2026) $
#$Revision: 304790 $
#$URL: svn://www.crystallography.net/cod/cif/7/06/43/7064332.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_7064332
loop_
_publ_author_name
'Nandhini, S.'
'Dharani, S.'
'Mugesh, B.'
'Prabusankar, G.'
'Mohanapriya, S.'
'Shankar, R.'
'Prabhakaran, R.'
_publ_section_title
;
 Bromoamination of α,β-unsaturated keto alkenes by palladium(ii)
 metalallocycles: experimental and theoretical approaches
;
_journal_issue                   3
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              1602
_journal_page_last               1612
_journal_paper_doi               10.1039/D5NJ02138C
_journal_volume                  50
_journal_year                    2026
_chemical_formula_moiety         'C18 H14 Cl N4 O Pd S, C3 H7 N O'
_chemical_formula_sum            'C21 H21 Cl N5 O2 Pd S'
_chemical_formula_weight         549.37
_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_Int_Tables_number      2
_atom_sites_solution_primary     iterative
_audit_creation_date             2022-02-05
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2023-12-28 deposited with the CCDC.	2025-12-22 downloaded from the CCDC.
;
_cell_angle_alpha                61.465(3)
_cell_angle_beta                 88.838(4)
_cell_angle_gamma                85.449(4)
_cell_formula_units_Z            2
_cell_length_a                   7.5069(8)
_cell_length_b                   12.9454(14)
_cell_length_c                   12.9847(14)
_cell_measurement_reflns_used    9993
_cell_measurement_temperature    273(2)
_cell_volume                     1104.8(2)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_temperature      273.15
_diffrn_measured_fraction_theta_full 0.9876
_diffrn_measured_fraction_theta_max 0.9876
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0512
_diffrn_reflns_av_unetI/netI     0.0367
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            29522
_diffrn_reflns_theta_full        27.1490
_diffrn_reflns_theta_max         27.15
_diffrn_reflns_theta_min         2.72
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.084
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.6697
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0845 before and 0.0627 after correction.
The Ratio of minimum to maximum transmission is 0.8983.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.6512
_exptl_crystal_description       needle
_exptl_crystal_F_000             552.7431
_exptl_crystal_size_max          0.079
_exptl_crystal_size_mid          0.071
_exptl_crystal_size_min          0.065
_refine_diff_density_max         2.7171
_refine_diff_density_min         -1.8643
_refine_diff_density_rms         0.2911
_refine_ls_d_res_high            0.7788
_refine_ls_d_res_low             7.4817
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_goodness_of_fit_ref   1.0377
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    36
_refine_ls_number_parameters     284
_refine_ls_number_reflns         4849
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0377
_refine_ls_R_factor_all          0.0980
_refine_ls_R_factor_gt           0.0871
_refine_ls_shift/su_max          0.0006
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1162P)²+29.7263P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2998
_refine_ls_wR_factor_ref         0.3094
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              9
_reflns_limit_h_min              -9
_reflns_limit_k_max              16
_reflns_limit_k_min              -14
_reflns_limit_l_max              16
_reflns_limit_l_min              0
_reflns_number_gt                4121
_reflns_number_total             4849
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            d5nj02138c2.cif
_cod_data_source_block           mo_GP_8MODP_3_0m_a
_cod_database_code               7064332
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C8(H8), C12(H12), C13(H13), C14(H14), C10(H10), C6(H6), C5(H5), C4(H4),
 C3(H3), C2(H2), C19(H19), N1(H1)
2.b Idealised Me refined as rotating group:
 C16(H16a,H16b,H16c), C20(H20a,H20b,H20c), C21(H21a,H21b,H21c)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -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_refinement_flags_posn
Pd1 Pd 0.81466(13) 0.73491(8) 0.42394(8) 0.0387(3) Uani 1.000000 .
S1 S 0.8784(5) 0.8738(3) 0.4686(3) 0.0478(7) Uani 1.000000 .
Cl1 Cl 0.7985(6) 0.8641(3) 0.2260(3) 0.0631(10) Uani 1.000000 .
O2 O 0.5562(18) 0.5520(10) 0.2007(9) 0.073(3) Uani 1.000000 .
N3 N 0.8407(16) 0.6299(9) 0.5918(9) 0.048(2) Uani 1.000000 .
N4 N 0.6881(14) 0.4245(9) 0.4260(9) 0.044(2) Uani 1.000000 .
O1 O 0.7447(16) 0.6036(8) 0.3919(9) 0.065(3) Uani 1.000000 .
N2 N 0.8888(16) 0.6669(10) 0.6732(10) 0.050(3) Uani 1.000000 .
N1 N 0.9490(15) 0.8341(9) 0.6830(9) 0.046(2) Uani 1.000000 .
C8 C 0.8258(18) 0.5139(11) 0.6472(11) 0.048(3) Uani 1.000000 .
H8 H 0.8530(18) 0.4726(11) 0.7271(11) 0.057(3) Uiso 1.000000 R
C9 C 0.7697(17) 0.4481(11) 0.5906(10) 0.042(2) Uani 1.000000 .
C18 C 0.7350(17) 0.4985(11) 0.4650(10) 0.043(3) Uani 1.000000 .
C17 C 0.6756(16) 0.3020(11) 0.4989(11) 0.043(3) Uani 1.000000 .
C11 C 0.7058(17) 0.2545(11) 0.6182(11) 0.044(3) Uani 1.000000 .
C12 C 0.688(2) 0.1346(12) 0.6903(13) 0.056(3) Uani 1.000000 .
H12 H 0.708(2) 0.1012(12) 0.7707(13) 0.067(4) Uiso 1.000000 R
C13 C 0.642(2) 0.0672(12) 0.6435(13) 0.056(3) Uani 1.000000 .
H13 H 0.627(2) -0.0123(12) 0.6918(13) 0.067(4) Uiso 1.000000 R
C14 C 0.618(2) 0.1170(13) 0.5221(16) 0.062(4) Uani 1.000000 .
H14 H 0.590(2) 0.0681(13) 0.4917(16) 0.075(5) Uiso 1.000000 R
C15 C 0.6324(16) 0.2327(12) 0.4463(13) 0.048(3) Uani 1.000000 .
C16 C 0.605(3) 0.2788(15) 0.3203(15) 0.072(5) Uani 1.000000 .
H16a H 0.584(18) 0.215(2) 0.305(2) 0.107(7) Uiso 1.000000 GR
H16b H 0.503(11) 0.336(9) 0.294(3) 0.107(7) Uiso 1.000000 GR
H16c H 0.709(7) 0.316(10) 0.2796(18) 0.107(7) Uiso 1.000000 GR
C10 C 0.7570(18) 0.3288(11) 0.6628(12) 0.049(3) Uani 1.000000 .
H10 H 0.7827(18) 0.2966(11) 0.7425(12) 0.059(3) Uiso 1.000000 R
C7 C 0.9051(18) 0.7811(11) 0.6197(11) 0.044(3) Uani 1.000000 .
C1 C 0.9522(18) 0.7922(11) 0.8057(11) 0.046(3) Uani 1.000000 .
C6 C 0.919(2) 0.6785(12) 0.8884(12) 0.055(3) Uani 1.000000 .
H6 H 0.896(2) 0.6235(12) 0.8646(12) 0.066(4) Uiso 1.000000 R
C5 C 0.920(2) 0.6463(14) 1.0077(13) 0.061(4) Uani 1.000000 .
H5 H 0.898(2) 0.5699(14) 1.0633(13) 0.073(4) Uiso 1.000000 R
C4 C 0.953(2) 0.7286(15) 1.0426(13) 0.065(4) Uani 1.000000 .
H4 H 0.950(2) 0.7082(15) 1.1217(13) 0.078(5) Uiso 1.000000 R
C3 C 0.992(2) 0.8394(14) 0.9619(14) 0.063(4) Uani 1.000000 .
H3 H 1.017(2) 0.8933(14) 0.9864(14) 0.076(5) Uiso 1.000000 R
C2 C 0.9922(19) 0.8727(12) 0.8421(12) 0.051(3) Uani 1.000000 .
H2 H 1.0192(19) 0.9483(12) 0.7874(12) 0.061(4) Uiso 1.000000 R
C19 C 0.549(2) 0.6597(14) 0.1520(13) 0.061(4) Uani 1.000000 .
H19 H 0.594(2) 0.6955(14) 0.1922(13) 0.074(4) Uiso 1.000000 R
N5 N 0.4805(19) 0.7284(13) 0.0451(12) 0.069(4) Uani 1.000000 .
C20 C 0.485(3) 0.856(2) -0.005(2) 0.115(9) Uani 1.000000 .
H20a H 0.53(3) 0.873(2) 0.053(6) 0.173(13) Uiso 1.000000 GR
H20b H 0.56(2) 0.885(3) -0.072(11) 0.173(13) Uiso 1.000000 GR
H20c H 0.366(5) 0.893(3) -0.027(17) 0.173(13) Uiso 1.000000 GR
C21 C 0.421(3) 0.674(2) -0.0218(18) 0.102(7) Uani 1.000000 .
H21a H 0.479(19) 0.596(6) 0.008(10) 0.153(11) Uiso 1.000000 GR
H21b H 0.294(5) 0.669(15) -0.015(13) 0.153(11) Uiso 1.000000 GR
H21c H 0.45(2) 0.721(9) -0.103(3) 0.153(11) Uiso 1.000000 GR
H1 H 0.9799(15) 0.9049(9) 0.6418(9) 0.055(3) Uiso 1.000000 R
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
Cl 0.14873 0.16029 11.46040 7.19640 6.25560 1.64550 0.01040 1.16620 18.51940
47.77840 -9.55739974976
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
S 0.12424 0.12443 6.90530 5.20340 1.43790 1.58630 1.46790 22.21510 0.25360
56.17200 0.866900026798
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
Pd -0.98845 1.01473 19.33190 15.50170 5.29537 0.60584 0.69866 7.98929 25.20520
76.89860 5.26593017578
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
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
_geom_angle_publ_flag
Cl1 Pd1 S1 92.96(12) . . ?
N3 Pd1 S1 84.6(3) . . ?
N3 Pd1 Cl1 176.7(3) . . ?
O1 Pd1 S1 176.2(3) . . ?
O1 Pd1 Cl1 89.8(3) . . ?
O1 Pd1 N3 92.8(4) . . ?
C7 S1 Pd1 96.4(4) . . ?
N2 N3 Pd1 123.6(8) . . ?
C8 N3 Pd1 126.6(8) . . ?
C8 N3 N2 109.7(10) . . ?
C17 N4 C18 124.0(10) . . ?
C18 O1 Pd1 126.7(8) . . ?
C7 N2 N3 110.4(11) . . ?
C1 N1 C7 130.6(11) . . ?
H1 N1 C7 114.7(7) . . ?
H1 N1 C1 114.7(6) . . ?
H8 C8 N3 118.0(7) . . ?
C9 C8 N3 124.1(11) . . ?
C9 C8 H8 118.0(7) . . ?
C18 C9 C8 124.5(11) . . ?
C10 C9 C8 115.9(11) . . ?
C10 C9 C18 119.5(11) . . ?
O1 C18 N4 117.8(11) . . ?
C9 C18 N4 117.0(11) . . ?
C9 C18 O1 125.1(11) . . ?
C11 C17 N4 118.9(10) . . ?
C15 C17 N4 118.6(11) . . ?
C15 C17 C11 122.6(12) . . ?
C12 C11 C17 118.9(12) . . ?
C10 C11 C17 118.9(11) . . ?
C10 C11 C12 122.2(13) . . ?
H12 C12 C11 120.0(8) . . ?
C13 C12 C11 120.0(14) . . ?
C13 C12 H12 120.0(9) . . ?
H13 C13 C12 120.1(9) . . ?
C14 C13 C12 119.8(13) . . ?
C14 C13 H13 120.1(8) . . ?
H14 C14 C13 118.2(8) . . ?
C15 C14 C13 123.7(13) . . ?
C15 C14 H14 118.2(9) . . ?
C14 C15 C17 115.0(13) . . ?
C16 C15 C17 124.3(12) . . ?
C16 C15 C14 120.7(13) . . ?
H16a C16 C15 109.5 . . ?
H16b C16 C15 109.5 . . ?
H16b C16 H16a 109.5 . . ?
H16c C16 C15 109.5 . . ?
H16c C16 H16a 109.5 . . ?
H16c C16 H16b 109.5 . . ?
C11 C10 C9 121.5(12) . . ?
H10 C10 C9 119.2(7) . . ?
H10 C10 C11 119.2(8) . . ?
N2 C7 S1 124.9(9) . . ?
N1 C7 S1 115.5(9) . . ?
N1 C7 N2 119.6(11) . . ?
C6 C1 N1 124.4(11) . . ?
C2 C1 N1 116.1(11) . . ?
C2 C1 C6 119.6(12) . . ?
H6 C6 C1 119.9(7) . . ?
C5 C6 C1 120.2(13) . . ?
C5 C6 H6 119.9(8) . . ?
H5 C5 C6 120.2(8) . . ?
C4 C5 C6 119.7(14) . . ?
C4 C5 H5 120.2(9) . . ?
H4 C4 C5 119.8(9) . . ?
C3 C4 C5 120.3(13) . . ?
C3 C4 H4 119.8(9) . . ?
H3 C3 C4 119.7(9) . . ?
C2 C3 C4 120.6(13) . . ?
C2 C3 H3 119.7(8) . . ?
C3 C2 C1 119.5(13) . . ?
H2 C2 C1 120.2(8) . . ?
H2 C2 C3 120.2(8) . . ?
H19 C19 O2 118.2(9) . . ?
N5 C19 O2 123.6(15) . . ?
N5 C19 H19 118.2(10) . . ?
C20 N5 C19 118.3(16) . . ?
C21 N5 C19 118.9(16) . . ?
C21 N5 C20 122.5(17) . . ?
H20a C20 N5 109.5 . . ?
H20b C20 N5 109.5 . . ?
H20b C20 H20a 109.5 . . ?
H20c C20 N5 109.5 . . ?
H20c C20 H20a 109.5 . . ?
H20c C20 H20b 109.5 . . ?
H21a C21 N5 109.5 . . ?
H21b C21 N5 109.5 . . ?
H21b C21 H21a 109.5 . . ?
H21c C21 N5 109.5 . . ?
H21c C21 H21a 109.5 . . ?
H21c C21 H21b 109.5 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Pd1 S1 2.223(3) . ?
Pd1 Cl1 2.300(3) . ?
Pd1 N3 1.944(11) . ?
Pd1 O1 2.041(9) . ?
S1 C7 1.749(13) . ?
O2 C19 1.223(19) . ?
N3 N2 1.416(13) . ?
N3 C8 1.332(16) . ?
N4 C18 1.350(15) . ?
N4 C17 1.416(15) . ?
O1 C18 1.239(15) . ?
N2 C7 1.314(16) . ?
N1 C7 1.357(15) . ?
N1 C1 1.417(16) . ?
N1 H1 0.8600 . ?
C8 H8 0.9300 . ?
C8 C9 1.454(16) . ?
C9 C18 1.458(16) . ?
C9 C10 1.381(18) . ?
C17 C11 1.383(18) . ?
C17 C15 1.420(16) . ?
C11 C12 1.393(17) . ?
C11 C10 1.417(17) . ?
C12 H12 0.9300 . ?
C12 C13 1.35(2) . ?
C13 H13 0.9300 . ?
C13 C14 1.40(2) . ?
C14 H14 0.9300 . ?
C14 C15 1.36(2) . ?
C15 C16 1.46(2) . ?
C16 H16a 0.9600 . ?
C16 H16b 0.9600 . ?
C16 H16c 0.9600 . ?
C10 H10 0.9300 . ?
C1 C6 1.385(18) . ?
C1 C2 1.389(16) . ?
C6 H6 0.9300 . ?
C6 C5 1.399(19) . ?
C5 H5 0.9300 . ?
C5 C4 1.38(2) . ?
C4 H4 0.9300 . ?
C4 C3 1.36(2) . ?
C3 H3 0.9300 . ?
C3 C2 1.40(2) . ?
C2 H2 0.9300 . ?
C19 H19 0.9300 . ?
C19 N5 1.33(2) . ?
N5 C20 1.46(3) . ?
N5 C21 1.45(2) . ?
C20 H20a 0.9600 . ?
C20 H20b 0.9600 . ?
C20 H20c 0.9600 . ?
C21 H21a 0.9600 . ?
C21 H21b 0.9600 . ?
C21 H21c 0.9600 . ?
