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#$Date: 2025-08-20 16:06:16 +0300 (Wed, 20 Aug 2025) $
#$Revision: 301830 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/07/69/4076991.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_4076991
loop_
_publ_author_name
'Vicente, José'
'Abad, José-Antonio'
'Martínez-Viviente, Eloísa'
'Jones, Peter G.'
_publ_section_title
;
 Study of the Reactivity of 2-Acetyl-, 2-Cyano-, 2-Formyl-, and
 2-Vinylphenyl Palladium(II) Complexes. Mono- and Triinsertion of an
 Isocyanide into the Pd−C Bond. A 2-Cyanophenyl Palladium Complex
 as a Ligand
;
_journal_issue                   21
_journal_name_full               Organometallics
_journal_page_first              4454
_journal_paper_doi               10.1021/om020380s
_journal_volume                  21
_journal_year                    2002
_chemical_formula_sum            'C44.5 H44 Br Cl N4 O Pd'
_chemical_formula_weight         872.60
_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     Patterson
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                95.774(3)
_cell_angle_beta                 92.752(3)
_cell_angle_gamma                98.372(3)
_cell_formula_units_Z            2
_cell_length_a                   8.1189(6)
_cell_length_b                   11.4137(8)
_cell_length_c                   21.9267(14)
_cell_measurement_reflns_used    7838
_cell_measurement_temperature    143(2)
_cell_measurement_theta_max      28
_cell_measurement_theta_min      2
_cell_volume                     1996.0(2)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Siemens XP'
_computing_publication_material  SHELXL-97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      143(2)
_diffrn_detector_area_resol_mean 8.192
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker SMART 1000 CCD'
_diffrn_measurement_method       'ω- and φ-scan'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0452
_diffrn_reflns_av_sigmaI/netI    0.0331
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            39038
_diffrn_reflns_theta_full        30.00
_diffrn_reflns_theta_max         30.03
_diffrn_reflns_theta_min         1.81
_exptl_absorpt_coefficient_mu    1.572
_exptl_absorpt_correction_T_max  0.7743
_exptl_absorpt_correction_T_min  0.6505
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   XPREP
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.452
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       tablet
_exptl_crystal_F_000             890
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.687
_refine_diff_density_min         -0.890
_refine_diff_density_rms         0.085
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    'rigid methyls, others riding'
_refine_ls_matrix_type           full
_refine_ls_number_parameters     496
_refine_ls_number_reflns         11633
_refine_ls_number_restraints     468
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0343
_refine_ls_R_factor_gt           0.0287
_refine_ls_shift/su_max          0.017
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0417P)²+0.3591P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0708
_refine_ls_wR_factor_ref         0.0733
_reflns_number_gt                10250
_reflns_number_total             11633
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om020380s.cif
_cod_data_source_block           piex
_cod_original_formula_sum        'C44.50 H44 Br Cl N4 O Pd'
_cod_database_code               4076991
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_group
Pd Pd 0.359144(13) 0.515014(10) 0.203959(5) 0.01654(4) Uani 1 1 d . .
Br Br 0.19367(2) 0.356062(15) 0.126277(7) 0.02723(4) Uani 1 1 d . .
N2 N 0.39879(14) 0.65900(11) 0.14942(5) 0.0176(2) Uani 1 1 d U .
N3 N 0.43076(17) 0.83476(11) 0.28364(6) 0.0223(3) Uani 1 1 d U .
N4 N 0.62451(16) 0.62430(11) 0.30248(6) 0.0196(2) Uani 1 1 d U .
N5 N 0.26872(17) 0.35670(12) 0.30666(6) 0.0227(3) Uani 1 1 d U .
O O 0.77810(15) 0.80656(11) 0.20192(6) 0.0288(2) Uani 1 1 d U .
C10 C 0.45667(17) 0.75975(13) 0.18068(7) 0.0187(3) Uani 1 1 d U .
C11 C 0.4800(2) 0.88033(14) 0.15917(7) 0.0229(3) Uani 1 1 d U .
C12 C 0.6337(2) 0.95681(15) 0.17037(8) 0.0273(3) Uani 1 1 d U .
C13 C 0.6436(3) 1.07355(17) 0.15505(10) 0.0406(4) Uani 1 1 d U .
H13 H 0.7467 1.1257 0.1621 0.049 Uiso 1 1 calc R .
C14 C 0.5063(3) 1.1147(2) 0.12976(12) 0.0509(6) Uani 1 1 d U .
H14 H 0.5152 1.1945 0.1199 0.061 Uiso 1 1 calc R .
C15 C 0.3562(3) 1.0393(2) 0.11899(12) 0.0465(5) Uani 1 1 d U .
H15 H 0.2618 1.0673 0.1017 0.056 Uiso 1 1 calc R .
C16 C 0.3425(2) 0.92253(17) 0.13334(9) 0.0326(4) Uani 1 1 d U .
H16 H 0.2390 0.8711 0.1255 0.039 Uiso 1 1 calc R .
C17 C 0.7820(2) 0.91219(16) 0.19699(8) 0.0284(3) Uani 1 1 d U .
C18 C 0.9364(3) 0.9991(2) 0.21857(12) 0.0466(5) Uani 1 1 d U .
H18A H 1.0232 0.9558 0.2335 0.056 Uiso 1 1 calc R .
H18B H 0.9101 1.0559 0.2519 0.056 Uiso 1 1 calc R .
H18C H 0.9762 1.0422 0.1844 0.056 Uiso 1 1 calc R .
C21 C 0.34660(18) 0.65340(14) 0.08492(6) 0.0198(3) Uani 1 1 d U .
C22 C 0.46572(19) 0.65322(15) 0.04119(7) 0.0223(3) Uani 1 1 d U .
C23 C 0.4108(2) 0.64916(17) -0.02036(7) 0.0286(3) Uani 1 1 d U .
H23 H 0.4892 0.6494 -0.0512 0.034 Uiso 1 1 calc R .
C24 C 0.2420(2) 0.64473(18) -0.03705(8) 0.0313(4) Uani 1 1 d U .
H24 H 0.2063 0.6437 -0.0790 0.038 Uiso 1 1 calc R .
C25 C 0.1265(2) 0.64191(17) 0.00726(8) 0.0297(4) Uani 1 1 d U .
H25 H 0.0115 0.6372 -0.0047 0.036 Uiso 1 1 calc R .
C26 C 0.17622(19) 0.64584(15) 0.06926(7) 0.0231(3) Uani 1 1 d U .
C27 C 0.6473(2) 0.65748(18) 0.05956(8) 0.0302(4) Uani 1 1 d U .
H27A H 0.6937 0.7378 0.0783 0.036 Uiso 1 1 calc R .
H27B H 0.7072 0.6374 0.0231 0.036 Uiso 1 1 calc R .
H27C H 0.6594 0.6001 0.0892 0.036 Uiso 1 1 calc R .
C28 C 0.0488(2) 0.64359(18) 0.11702(8) 0.0291(3) Uani 1 1 d U .
H28A H 0.1024 0.6352 0.1570 0.035 Uiso 1 1 calc R .
H28B H -0.0402 0.5761 0.1056 0.035 Uiso 1 1 calc R .
H28C H 0.0014 0.7180 0.1195 0.035 Uiso 1 1 calc R .
C30 C 0.47454(18) 0.75124(13) 0.24823(7) 0.0183(3) Uani 1 1 d U .
C31 C 0.4046(2) 0.82309(14) 0.34644(7) 0.0246(3) Uani 1 1 d U .
C32 C 0.5285(3) 0.87393(16) 0.39162(8) 0.0331(4) Uani 1 1 d U .
C33 C 0.4884(3) 0.87172(18) 0.45311(9) 0.0442(5) Uani 1 1 d U .
H33 H 0.5711 0.9037 0.4849 0.053 Uiso 1 1 calc R .
C34 C 0.3318(4) 0.82417(18) 0.46842(9) 0.0472(6) Uani 1 1 d U .
H34 H 0.3071 0.8248 0.5104 0.057 Uiso 1 1 calc R .
C35 C 0.2110(3) 0.77570(17) 0.42291(9) 0.0412(5) Uani 1 1 d U .
H35 H 0.1034 0.7433 0.4339 0.049 Uiso 1 1 calc R .
C36 C 0.2441(2) 0.77336(15) 0.36093(8) 0.0302(4) Uani 1 1 d U .
C37 C 0.6973(3) 0.9259(2) 0.37380(10) 0.0445(5) Uani 1 1 d U .
H37A H 0.7511 0.8626 0.3532 0.053 Uiso 1 1 calc R .
H37B H 0.7659 0.9626 0.4107 0.053 Uiso 1 1 calc R .
H37C H 0.6854 0.9863 0.3458 0.053 Uiso 1 1 calc R .
C38 C 0.1115(2) 0.72196(18) 0.31123(9) 0.0368(4) Uani 1 1 d U .
H38A H 0.0058 0.6989 0.3298 0.044 Uiso 1 1 calc R .
H38B H 0.1448 0.6517 0.2885 0.044 Uiso 1 1 calc R .
H38C H 0.0976 0.7818 0.2831 0.044 Uiso 1 1 calc R .
C40 C 0.50933(18) 0.63211(13) 0.26300(6) 0.0175(3) Uani 1 1 d U .
C41 C 0.66447(18) 0.51398(13) 0.31798(7) 0.0204(3) Uani 1 1 d U .
C42 C 0.6426(2) 0.48819(15) 0.37875(7) 0.0255(3) Uani 1 1 d U .
C43 C 0.6756(2) 0.37878(17) 0.39506(9) 0.0350(4) Uani 1 1 d U .
H43 H 0.6549 0.3582 0.4352 0.042 Uiso 1 1 calc R .
C44 C 0.7381(3) 0.29996(17) 0.35369(10) 0.0402(5) Uani 1 1 d U .
H44 H 0.7583 0.2250 0.3651 0.048 Uiso 1 1 calc R .
C45 C 0.7712(3) 0.33029(16) 0.29539(9) 0.0357(4) Uani 1 1 d U .
H45 H 0.8198 0.2772 0.2680 0.043 Uiso 1 1 calc R .
C46 C 0.7348(2) 0.43748(15) 0.27594(8) 0.0254(3) Uani 1 1 d U .
C47 C 0.5862(3) 0.5790(2) 0.42468(8) 0.0388(4) Uani 1 1 d U .
H47A H 0.5744 0.5464 0.4642 0.047 Uiso 1 1 calc R .
H47B H 0.4786 0.5982 0.4098 0.047 Uiso 1 1 calc R .
H47C H 0.6691 0.6514 0.4299 0.047 Uiso 1 1 calc R .
C48 C 0.7728(2) 0.46908(19) 0.21275(8) 0.0344(4) Uani 1 1 d U .
H48A H 0.8661 0.4302 0.1985 0.041 Uiso 1 1 calc R .
H48B H 0.8028 0.5557 0.2139 0.041 Uiso 1 1 calc R .
H48C H 0.6743 0.4420 0.1845 0.041 Uiso 1 1 calc R .
C50 C 0.31188(19) 0.41210(14) 0.26777(7) 0.0210(3) Uani 1 1 d U .
C51 C 0.22080(19) 0.28492(14) 0.35256(7) 0.0226(3) Uani 1 1 d U .
C52 C 0.2501(2) 0.16651(15) 0.34419(9) 0.0295(3) Uani 1 1 d U .
C53 C 0.1993(3) 0.09521(19) 0.38997(11) 0.0438(5) Uani 1 1 d U .
H53 H 0.2161 0.0142 0.3863 0.053 Uiso 1 1 calc R .
C54 C 0.1249(3) 0.1410(2) 0.44049(11) 0.0491(6) Uani 1 1 d U .
H54 H 0.0902 0.0908 0.4710 0.059 Uiso 1 1 calc R .
C55 C 0.1001(3) 0.2586(2) 0.44751(9) 0.0423(5) Uani 1 1 d U .
H55 H 0.0500 0.2882 0.4830 0.051 Uiso 1 1 calc R .
C56 C 0.1476(2) 0.33473(16) 0.40327(8) 0.0292(3) Uani 1 1 d U .
C57 C 0.3340(3) 0.12247(17) 0.28882(11) 0.0413(5) Uani 1 1 d U .
H57A H 0.3361 0.0368 0.2886 0.050 Uiso 1 1 calc R .
H57B H 0.4485 0.1646 0.2901 0.050 Uiso 1 1 calc R .
H57C H 0.2722 0.1372 0.2515 0.050 Uiso 1 1 calc R .
C58 C 0.1192(3) 0.46173(19) 0.40946(10) 0.0422(5) Uani 1 1 d U .
H58A H 0.2238 0.5135 0.4042 0.051 Uiso 1 1 calc R .
H58B H 0.0806 0.4824 0.4503 0.051 Uiso 1 1 calc R .
H58C H 0.0347 0.4726 0.3779 0.051 Uiso 1 1 calc R .
C99 C -0.0629(13) 0.0756(7) 0.0199(4) 0.0408(19) Uiso 0.295(5) 1 d PDU 1
H99A H -0.0168 0.1350 0.0548 0.049 Uiso 0.295(5) 1 calc PR 1
H99B H -0.1712 0.0948 0.0044 0.049 Uiso 0.295(5) 1 calc PR 1
Cl Cl 0.0852(2) 0.0713(2) -0.04194(8) 0.0663(9) Uani 0.589(11) 1 d PDU 1
C99' C -0.031(4) 0.0825(16) 0.0162(10) 0.100(8) Uiso 0.205(5) 1 d PDU 2
H99C H -0.1418 0.1026 0.0115 0.120 Uiso 0.205(5) 1 d PR 2
H99D H 0.0208 0.1250 0.0538 0.120 Uiso 0.205(5) 1 d PR 2
Cl' Cl 0.0829(11) 0.0513(9) -0.0502(4) 0.230(5) Uani 0.411(11) 1 d PDU 2
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'
Br Br -0.2901 2.4595 '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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0.00 1.00 0.00 0.1560
0.00 0.00 -1.00 0.1210
0.00 0.00 1.00 0.1230
-1.00 0.00 1.00 0.1000
1.00 0.00 -1.00 0.1320
0.00 -1.00 1.00 0.1270
0.00 1.00 -1.00 0.1450
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
C50 Pd C40 90.54(6) .
C50 Pd N2 166.75(6) .
C40 Pd N2 80.72(5) .
C50 Pd Br 89.47(4) .
C40 Pd Br 174.19(4) .
N2 Pd Br 100.23(3) .
C10 N2 C21 120.62(13) .
C10 N2 Pd 113.57(10) .
C21 N2 Pd 125.28(10) .
C30 N3 C31 121.78(13) .
C40 N4 C41 122.88(13) .
C50 N5 C51 177.04(16) .
N2 C10 C11 128.14(14) .
N2 C10 C30 112.90(13) .
C11 C10 C30 118.17(13) .
C16 C11 C12 119.58(15) .
C16 C11 C10 119.09(14) .
C12 C11 C10 120.98(14) .
C13 C12 C11 118.61(17) .
C13 C12 C17 121.32(16) .
C11 C12 C17 120.06(15) .
C14 C13 C12 121.36(19) .
C15 C14 C13 119.64(19) .
C14 C15 C16 120.4(2) .
C15 C16 C11 120.40(18) .
O C17 C12 120.44(15) .
O C17 C18 120.11(17) .
C12 C17 C18 119.45(16) .
C22 C21 C26 122.70(14) .
C22 C21 N2 119.51(13) .
C26 C21 N2 117.78(12) .
C21 C22 C23 117.80(14) .
C21 C22 C27 121.25(14) .
C23 C22 C27 120.94(14) .
C24 C23 C22 120.58(15) .
C25 C24 C23 120.22(15) .
C24 C25 C26 120.98(15) .
C25 C26 C21 117.68(14) .
C25 C26 C28 120.31(14) .
C21 C26 C28 122.01(14) .
N3 C30 C40 128.68(13) .
N3 C30 C10 117.12(13) .
C40 C30 C10 112.92(12) .
C32 C31 C36 122.22(15) .
C32 C31 N3 119.88(15) .
C36 C31 N3 117.38(15) .
C31 C32 C33 117.28(19) .
C31 C32 C37 120.16(16) .
C33 C32 C37 122.55(19) .
C34 C33 C32 121.5(2) .
C33 C34 C35 120.04(17) .
C34 C35 C36 121.2(2) .
C35 C36 C31 117.75(19) .
C35 C36 C38 121.15(18) .
C31 C36 C38 121.09(15) .
N4 C40 C30 120.27(13) .
N4 C40 Pd 134.44(11) .
C30 C40 Pd 105.01(10) .
C46 C41 C42 121.27(15) .
C46 C41 N4 121.42(14) .
C42 C41 N4 117.15(14) .
C43 C42 C41 118.67(16) .
C43 C42 C47 121.50(16) .
C41 C42 C47 119.82(15) .
C44 C43 C42 120.83(17) .
C43 C44 C45 119.90(17) .
C44 C45 C46 121.52(18) .
C45 C46 C41 117.49(16) .
C45 C46 C48 120.69(16) .
C41 C46 C48 121.81(15) .
N5 C50 Pd 172.59(14) .
N5 C51 C56 118.52(15) .
N5 C51 C52 117.02(15) .
C56 C51 C52 124.46(15) .
C53 C52 C51 116.43(18) .
C53 C52 C57 123.22(18) .
C51 C52 C57 120.34(16) .
C54 C53 C52 120.8(2) .
C53 C54 C55 121.12(18) .
C54 C55 C56 121.0(2) .
C51 C56 C55 116.17(18) .
C51 C56 C58 121.92(16) .
C55 C56 C58 121.90(18) .
Cl C99 Cl 103.4(4) 2
C99 Cl C99 76.6(4) 2
Cl' C99' Cl' 108.4(10) 2
C99' Cl' C99' 71.6(10) 2
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Pd C50 1.9327(16) .
Pd C40 1.9936(15) .
Pd N2 2.1243(12) .
Pd Br 2.5390(2) .
N2 C10 1.2908(19) .
N2 C21 1.4491(18) .
N3 C30 1.2704(19) .
N3 C31 1.4198(19) .
N4 C40 1.2624(19) .
N4 C41 1.415(2) .
N5 C50 1.150(2) .
N5 C51 1.3949(19) .
O C17 1.217(2) .
C10 C11 1.489(2) .
C10 C30 1.496(2) .
C11 C16 1.396(2) .
C11 C12 1.411(2) .
C12 C13 1.399(2) .
C12 C17 1.490(2) .
C13 C14 1.385(3) .
C14 C15 1.381(3) .
C15 C16 1.390(3) .
C17 C18 1.505(3) .
C21 C22 1.394(2) .
C21 C26 1.397(2) .
C22 C23 1.395(2) .
C22 C27 1.502(2) .
C23 C24 1.394(2) .
C24 C25 1.382(2) .
C25 C26 1.394(2) .
C26 C28 1.506(2) .
C30 C40 1.492(2) .
C31 C32 1.396(3) .
C31 C36 1.408(3) .
C32 C33 1.404(3) .
C32 C37 1.498(3) .
C33 C34 1.378(4) .
C34 C35 1.379(3) .
C35 C36 1.396(2) .
C36 C38 1.505(3) .
C41 C46 1.404(2) .
C41 C42 1.407(2) .
C42 C43 1.392(2) .
C42 C47 1.506(3) .
C43 C44 1.379(3) .
C44 C45 1.386(3) .
C45 C46 1.402(2) .
C46 C48 1.501(2) .
C51 C56 1.396(2) .
C51 C52 1.402(2) .
C52 C53 1.395(3) .
C52 C57 1.499(3) .
C53 C54 1.380(4) .
C54 C55 1.380(4) .
C55 C56 1.398(3) .
C56 C58 1.494(3) .
C99 Cl 1.778(7) 2
C99 Cl 1.857(8) .
Cl C99 1.778(7) 2
C99' Cl' 1.770(14) 2
C99' Cl' 1.797(14) .
Cl' C99' 1.770(14) 2
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139106361
