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#$Date: 2025-08-20 17:59:05 +0300 (Wed, 20 Aug 2025) $
#$Revision: 301833 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/11/96/4119682.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_4119682
loop_
_publ_author_name
'Ansis Maleckis'
'Jeff W. Kampf'
'Melanie S. Sanford'
_publ_section_title
;
 A Detailed Study of Acetate-Assisted C-H Activation at Palladium(IV)
 Centers
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              6618
_journal_page_last               6625
_journal_paper_doi               10.1021/ja401557m
_journal_volume                  135
_journal_year                    2013
_chemical_formula_moiety         'C28 H22 I N3 Pd'
_chemical_formula_sum            'C28 H22 I N3 Pd'
_chemical_formula_weight         633.79
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_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                 101.232(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.3934(2)
_cell_length_b                   14.7202(3)
_cell_length_c                   17.5207(12)
_cell_measurement_reflns_used    46120
_cell_measurement_temperature    85(2)
_cell_measurement_theta_max      68.30
_cell_measurement_theta_min      2.60
_cell_volume                     2376.23(19)
_computing_cell_refinement       'CrystalClear-SM Expert 2.0 r12'
_computing_data_collection       'CrystalClear-SM Expert 2.0 r12 (Rigaku, 2011)'
_computing_data_reduction        'CrystalClear-SM Expert 2.0 r12'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      85(2)
_diffrn_detector_area_resol_mean 14.629
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Rigaku Saturn944+ CCD'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0687
_diffrn_reflns_av_sigmaI/netI    0.0319
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            60719
_diffrn_reflns_theta_full        68.23
_diffrn_reflns_theta_max         68.23
_diffrn_reflns_theta_min         5.15
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    16.657
_exptl_absorpt_correction_T_max  0.6349
_exptl_absorpt_correction_T_min  0.4348
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
    Higashi, T. (1995). Program for Absorption Correction.
    Rigaku Corporation, Tokyo, Japan.
;
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.772
_exptl_crystal_description       block
_exptl_crystal_F_000             1240
_exptl_crystal_size_max          0.06
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.03
_refine_diff_density_max         1.392
_refine_diff_density_min         -0.984
_refine_diff_density_rms         0.109
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     298
_refine_ls_number_reflns         4344
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.0329
_refine_ls_R_factor_gt           0.0320
_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)+(0.0366P)²+6.4117P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0825
_refine_ls_wR_factor_ref         0.0832
_reflns_number_gt                4154
_reflns_number_total             4344
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja401557m_si_001_3.cif
_cod_data_source_block           COMPLEX7
_cod_original_cell_volume        2376.23(18)
_cod_database_code               4119682
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 0.40300(2) 0.225767(16) 0.198008(14) 0.02600(9) Uani 1 1 d . . .
Pd1 Pd 0.13579(3) 0.225519(17) 0.119683(15) 0.02090(9) Uani 1 1 d . . .
C1 C -0.1923(4) 0.2424(3) 0.0827(2) 0.0251(8) Uani 1 1 d . . .
H1A H -0.1824 0.2364 0.1374 0.030 Uiso 1 1 calc R . .
C2 C -0.3297(4) 0.2533(3) 0.0379(2) 0.0266(8) Uani 1 1 d . . .
H2A H -0.4127 0.2535 0.0614 0.032 Uiso 1 1 calc R . .
C3 C -0.3443(4) 0.2640(3) -0.0417(2) 0.0300(9) Uani 1 1 d . . .
H3A H -0.4372 0.2738 -0.0734 0.036 Uiso 1 1 calc R . .
C4 C -0.2217(4) 0.2601(2) -0.0745(2) 0.0265(8) Uani 1 1 d . . .
H4A H -0.2301 0.2658 -0.1292 0.032 Uiso 1 1 calc R . .
C5 C -0.0869(4) 0.2480(2) -0.0272(2) 0.0234(7) Uani 1 1 d . . .
C6 C 0.0493(4) 0.2442(3) -0.0617(2) 0.0251(8) Uani 1 1 d . A .
H6A H 0.0161 0.2470 -0.1194 0.030 Uiso 1 1 calc R . .
C7 C 0.1249(4) 0.1538(3) -0.0442(2) 0.0277(8) Uani 1 1 d . . .
C8 C 0.1355(5) 0.0930(3) -0.1038(3) 0.0353(9) Uani 1 1 d . . .
H8A H 0.1000 0.1090 -0.1566 0.042 Uiso 1 1 calc R . .
C9 C 0.1987(6) 0.0088(3) -0.0849(3) 0.0431(11) Uani 1 1 d . . .
H9A H 0.2072 -0.0337 -0.1245 0.052 Uiso 1 1 calc R . .
C10 C 0.2492(6) -0.0123(3) -0.0071(3) 0.0448(11) Uani 1 1 d . . .
H10A H 0.2934 -0.0695 0.0073 0.054 Uiso 1 1 calc R . .
C11 C 0.2344(5) 0.0508(3) 0.0487(3) 0.0353(9) Uani 1 1 d . . .
H11A H 0.2684 0.0359 0.1019 0.042 Uiso 1 1 calc R . .
C12 C 0.1439(4) 0.3284(3) -0.0389(2) 0.0258(8) Uani 1 1 d . . .
C13 C 0.2871(4) 0.3215(3) -0.0058(2) 0.0335(8) Uani 0.50 1 d P A 1
H13 H 0.3340 0.2640 0.0016 0.040 Uiso 0.50 1 calc PR A 1
N3A N 0.2871(4) 0.3215(3) -0.0058(2) 0.0335(8) Uani 0.50 1 d P A 2
C14 C 0.3616(5) 0.4007(3) 0.0164(3) 0.0365(9) Uani 1 1 d . . .
H14A H 0.4608 0.3978 0.0413 0.044 Uiso 1 1 calc R A 1
C15 C 0.2952(5) 0.4835(3) 0.0034(3) 0.0368(10) Uani 1 1 d . A .
H15A H 0.3465 0.5378 0.0200 0.044 Uiso 1 1 calc R . .
C16 C 0.1529(5) 0.4862(3) -0.0344(3) 0.0430(11) Uani 1 1 d . . .
H16A H 0.1072 0.5434 -0.0464 0.052 Uiso 1 1 calc R A 1
C17 C 0.0865(4) 0.3114(2) 0.1978(2) 0.0241(7) Uani 1 1 d . . .
C18 C 0.1193(4) 0.4028(3) 0.1887(2) 0.0291(8) Uani 1 1 d . . .
H18A H 0.1716 0.4194 0.1495 0.035 Uiso 1 1 calc R . .
C19 C 0.0775(4) 0.4699(3) 0.2354(3) 0.0334(9) Uani 1 1 d . . .
H19A H 0.1010 0.5317 0.2281 0.040 Uiso 1 1 calc R . .
C20 C 0.0017(4) 0.4464(3) 0.2924(2) 0.0333(9) Uani 1 1 d . . .
H20A H -0.0273 0.4919 0.3247 0.040 Uiso 1 1 calc R . .
C21 C -0.0321(4) 0.3563(3) 0.3024(2) 0.0284(8) Uani 1 1 d . . .
H21A H -0.0848 0.3407 0.3416 0.034 Uiso 1 1 calc R . .
C22 C 0.0097(4) 0.2873(3) 0.2561(2) 0.0245(8) Uani 1 1 d . . .
C23 C -0.0331(4) 0.1919(3) 0.2693(2) 0.0263(8) Uani 1 1 d . . .
C24 C -0.1712(4) 0.1734(3) 0.2845(2) 0.0302(8) Uani 1 1 d . . .
H24A H -0.2368 0.2223 0.2856 0.036 Uiso 1 1 calc R . .
C25 C -0.2150(4) 0.0862(3) 0.2980(2) 0.0343(9) Uani 1 1 d . . .
H25A H -0.3100 0.0758 0.3073 0.041 Uiso 1 1 calc R . .
C26 C -0.1200(5) 0.0140(3) 0.2981(2) 0.0358(9) Uani 1 1 d . . .
H26A H -0.1494 -0.0459 0.3080 0.043 Uiso 1 1 calc R . .
C27 C 0.0187(4) 0.0297(3) 0.2834(2) 0.0295(8) Uani 1 1 d . . .
H27A H 0.0843 -0.0194 0.2833 0.035 Uiso 1 1 calc R . .
C28 C 0.0603(4) 0.1179(3) 0.2690(2) 0.0270(8) Uani 1 1 d . . .
H28A H 0.1547 0.1281 0.2587 0.032 Uiso 1 1 calc R . .
N1 N -0.0717(3) 0.2400(2) 0.05147(18) 0.0207(6) Uani 1 1 d . . .
N2 N 0.1737(4) 0.1325(2) 0.03100(19) 0.0288(7) Uani 1 1 d . . .
N3 N 0.0755(4) 0.4085(3) -0.0551(2) 0.0342(8) Uani 0.50 1 d P A 1
C13A C 0.0755(4) 0.4085(3) -0.0551(2) 0.0342(8) Uani 0.50 1 d P A 2
H13A H -0.0236 0.4108 -0.0803 0.041 Uiso 0.50 1 calc PR 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'
Pd Pd 0.1215 3.9337 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.3257 6.8362 '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
C17 Pd1 N1 90.73(13)
C17 Pd1 N2 176.04(13)
N1 Pd1 N2 85.36(12)
C17 Pd1 I1 88.06(10)
N1 Pd1 I1 173.17(8)
N2 Pd1 I1 95.89(9)
N1 C1 C2 122.5(4)
C3 C2 C1 118.9(4)
C2 C3 C4 119.1(4)
C5 C4 C3 119.6(4)
N1 C5 C4 121.4(4)
N1 C5 C6 118.0(3)
C4 C5 C6 120.6(3)
C7 C6 C5 110.5(3)
C7 C6 C12 115.7(3)
C5 C6 C12 110.9(3)
N2 C7 C8 121.6(4)
N2 C7 C6 117.4(3)
C8 C7 C6 120.9(4)
C9 C8 C7 119.0(4)
C8 C9 C10 118.9(4)
C11 C10 C9 118.9(4)
N2 C11 C10 122.6(4)
N3 C12 C13 123.2(4)
N3 C12 C6 115.1(3)
C13 C12 C6 121.7(3)
C12 C13 C14 117.5(4)
C15 C14 C13 121.2(4)
C14 C15 C16 118.5(4)
N3 C16 C15 121.4(4)
C18 C17 C22 118.9(3)
C18 C17 Pd1 116.6(3)
C22 C17 Pd1 124.2(3)
C19 C18 C17 121.6(4)
C20 C19 C18 119.6(4)
C19 C20 C21 119.7(4)
C20 C21 C22 121.7(4)
C21 C22 C17 118.6(4)
C21 C22 C23 118.6(3)
C17 C22 C23 122.8(3)
C28 C23 C24 117.0(4)
C28 C23 C22 123.0(3)
C24 C23 C22 120.0(4)
C25 C24 C23 122.0(4)
C24 C25 C26 119.9(4)
C25 C26 C27 119.8(4)
C28 C27 C26 119.5(4)
C27 C28 C23 121.8(4)
C1 N1 C5 118.4(3)
C1 N1 Pd1 122.3(2)
C5 N1 Pd1 119.3(3)
C11 N2 C7 118.9(3)
C11 N2 Pd1 121.8(3)
C7 N2 Pd1 119.1(2)
C12 N3 C16 118.0(4)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
I1 Pd1 2.6156(4)
Pd1 C17 1.984(4)
Pd1 N1 2.089(3)
Pd1 N2 2.152(3)
C1 N1 1.351(5)
C1 C2 1.383(6)
C2 C3 1.382(6)
C3 C4 1.385(6)
C4 C5 1.383(5)
C5 N1 1.362(5)
C5 C6 1.518(5)
C6 C7 1.512(5)
C6 C12 1.532(5)
C7 N2 1.345(5)
C7 C8 1.394(6)
C8 C9 1.386(6)
C9 C10 1.388(7)
C10 C11 1.376(6)
C11 N2 1.342(5)
C12 N3 1.345(5)
C12 C13 1.361(5)
C13 C14 1.377(6)
C14 C15 1.368(6)
C15 C16 1.372(7)
C16 N3 1.367(6)
C17 C18 1.396(5)
C17 C22 1.406(5)
C18 C19 1.387(6)
C19 C20 1.380(6)
C20 C21 1.382(6)
C21 C22 1.402(5)
C22 C23 1.491(5)
C23 C28 1.399(5)
C23 C24 1.402(5)
C24 C25 1.381(6)
C25 C26 1.388(6)
C26 C27 1.395(6)
C27 C28 1.394(5)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139122039
