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#$Date: 2025-08-20 15:05:43 +0300 (Wed, 20 Aug 2025) $
#$Revision: 301829 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/06/34/4063481.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_4063481
loop_
_publ_author_name
'Chan, Kai-Ting'
'Tsai, Yi-Hua'
'Lin, Wu-Shien'
'Wu, Jia-Rong'
'Chen, Shih-Jung'
'Liao, Fu-Xing'
'Hu, Ching-Han'
'Lee, Hon Man'
_publ_section_title
;
 Palladium Complexes with Carbene and Phosphine Ligands: Synthesis,
 Structural Characterization, and Direct Arylation Reactions between Aryl
 Halides and Alkynes
;
_journal_issue                   2
_journal_name_full               Organometallics
_journal_page_first              463
_journal_page_last               472
_journal_paper_doi               10.1021/om9009203
_journal_volume                  29
_journal_year                    2010
_chemical_formula_moiety         'C20 H14'
_chemical_formula_sum            'C20 H14'
_chemical_formula_weight         254.31
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      15
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 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                 119.881(11)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   23.555(15)
_cell_length_b                   7.215(5)
_cell_length_c                   19.145(13)
_cell_measurement_reflns_used    5174
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.3
_cell_measurement_theta_min      2.3
_cell_volume                     2821(3)
_computing_cell_refinement       APEX2
_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_data_reduction        APEX2
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL
_computing_structure_refinement  SHELXTL
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker SMART APEX II'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0328
_diffrn_reflns_av_sigmaI/netI    0.0298
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            19661
_diffrn_reflns_theta_full        29.05
_diffrn_reflns_theta_max         29.05
_diffrn_reflns_theta_min         1.99
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.068
_exptl_absorpt_correction_T_max  0.9913
_exptl_absorpt_correction_T_min  0.9669
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS 2.10 (Sheldrick, 2003)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.197
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1072
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.186
_refine_diff_density_min         -0.115
_refine_diff_density_rms         0.030
_refine_ls_extinction_coef       0.0035(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     224
_refine_ls_number_reflns         3754
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.021
_refine_ls_R_factor_all          0.0747
_refine_ls_R_factor_gt           0.0506
_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)+(0.0803P)²+1.0396P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1579
_refine_ls_wR_factor_ref         0.1766
_reflns_number_gt                2515
_reflns_number_total             3754
_reflns_threshold_expression     I>2σ
_cod_data_source_file            om9009203_si_001.cif
_cod_data_source_block           9
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               4063481
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.11000(7) 0.1404(2) 0.11258(8) 0.0540(4) Uani 1 1 d . B .
C2 C 0.11455(7) 0.0475(2) 0.18384(9) 0.0558(4) Uani 1 1 d . . .
C3 C 0.08114(9) 0.0747(3) 0.22471(11) 0.0698(5) Uani 1 1 d . . .
H3A H 0.0475 0.1654 0.2067 0.084 Uiso 1 1 calc R . .
C4 C 0.09657(10) -0.0294(3) 0.29151(12) 0.0837(6) Uani 1 1 d . . .
H4A H 0.0737 -0.0101 0.3200 0.100 Uiso 1 1 calc R . .
C5 C 0.14434(11) -0.1603(3) 0.31755(13) 0.0871(6) Uani 1 1 d . . .
H5A H 0.1543 -0.2320 0.3639 0.105 Uiso 1 1 calc R . .
C6 C 0.17818(9) -0.1897(3) 0.27768(11) 0.0771(5) Uani 1 1 d . . .
H6A H 0.2115 -0.2813 0.2961 0.092 Uiso 1 1 calc R . .
C7 C 0.16355(7) -0.0855(2) 0.21065(9) 0.0579(4) Uani 1 1 d . . .
C8 C 0.19207(7) -0.0818(2) 0.15851(9) 0.0587(4) Uani 1 1 d . . .
C9 C 0.24247(8) -0.1830(3) 0.16090(12) 0.0769(5) Uani 1 1 d . . .
H9A H 0.2640 -0.2757 0.2008 0.092 Uiso 1 1 calc R . .
C10 C 0.26121(9) -0.1483(3) 0.10487(14) 0.0849(6) Uani 1 1 d . . .
H10A H 0.2961 -0.2174 0.1062 0.102 Uiso 1 1 calc R . .
C11 C 0.23051(9) -0.0158(3) 0.04725(12) 0.0794(5) Uani 1 1 d . . .
H11A H 0.2444 0.0066 0.0092 0.095 Uiso 1 1 calc R . .
C12 C 0.17979(8) 0.0857(3) 0.04341(10) 0.0675(4) Uani 1 1 d . . .
H12A H 0.1582 0.1766 0.0026 0.081 Uiso 1 1 calc R . .
C13 C 0.16062(7) 0.0537(2) 0.09989(9) 0.0543(4) Uani 1 1 d . . .
C14 C 0.06881(8) 0.2731(3) 0.07035(10) 0.0665(4) Uani 1 1 d . . .
H14B H 0.0724 0.3191 0.0262 0.080 Uiso 0.25 1 calc PR A 2
H14A H 0.0401 0.3113 0.0877 0.080 Uiso 0.75 1 d PR A 1
C15 C 0.06257(10) 0.3677(3) -0.00041(14) 0.0626(5) Uani 0.75 1 d P B 1
C16 C 0.01965(14) 0.3094(4) -0.07653(15) 0.0782(7) Uani 0.75 1 d P B 1
H16A H -0.0080 0.2062 -0.0846 0.094 Uiso 0.75 1 calc PR B 1
C17 C 0.0163(2) 0.4002(8) -0.1418(2) 0.088(3) Uani 0.75 1 d P B 1
H17A H -0.0149 0.3615 -0.1948 0.106 Uiso 0.75 1 calc PR B 1
C18 C 0.0563(2) 0.5417(5) -0.1319(2) 0.0785(9) Uani 0.75 1 d P B 1
H18A H 0.0564 0.5953 -0.1771 0.094 Uiso 0.75 1 calc PR B 1
C19 C 0.0955(2) 0.6065(9) -0.0590(3) 0.0922(13) Uani 0.75 1 d P B 1
H19A H 0.1206 0.7149 -0.0522 0.111 Uiso 0.75 1 calc PR B 1
C20 C 0.10040(12) 0.5174(4) 0.00811(17) 0.0842(7) Uani 0.75 1 d P B 1
H20A H 0.1305 0.5617 0.0605 0.101 Uiso 0.75 1 calc PR B 1
C15A C 0.01968(17) 0.3564(5) 0.0822(2) 0.0478(11) Uani 0.25 1 d PG B 2
C16A C -0.0413(2) 0.2709(6) 0.0453(3) 0.0679(16) Uani 0.25 1 d PG B 2
H16B H -0.0489 0.1649 0.0123 0.082 Uiso 0.25 1 calc PR B 2
C17A C -0.0912(2) 0.3405(10) 0.0565(5) 0.094(6) Uani 0.25 1 d PG B 2
H17B H -0.1329 0.2820 0.0312 0.113 Uiso 0.25 1 calc PR B 2
C18A C -0.0801(3) 0.4955(11) 0.1047(5) 0.082(4) Uani 0.25 1 d PG B 2
H18B H -0.1142 0.5431 0.1124 0.098 Uiso 0.25 1 calc PR B 2
C19A C -0.0191(3) 0.5811(8) 0.1417(4) 0.089(9) Uani 0.25 1 d PG B 2
H19B H -0.0116 0.6870 0.1746 0.107 Uiso 0.25 1 calc PR B 2
C20A C 0.0308(2) 0.5115(6) 0.1304(3) 0.0617(14) Uani 0.25 1 d PG B 2
H20B H 0.0724 0.5699 0.1557 0.074 Uiso 0.25 1 calc PR B 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'
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
C14 C1 C13 128.22(15) . . ?
C14 C1 C2 126.22(14) . . ?
C13 C1 C2 105.56(13) . . ?
C3 C2 C7 119.71(15) . . ?
C3 C2 C1 131.60(15) . . ?
C7 C2 C1 108.67(13) . . ?
C4 C3 C2 119.59(18) . . ?
C4 C3 H3A 120.2 . . ?
C2 C3 H3A 120.2 . . ?
C5 C4 C3 120.72(19) . . ?
C5 C4 H4A 119.6 . . ?
C3 C4 H4A 119.6 . . ?
C4 C5 C6 120.62(19) . . ?
C4 C5 H5A 119.7 . . ?
C6 C5 H5A 119.7 . . ?
C5 C6 C7 119.44(18) . . ?
C5 C6 H6A 120.3 . . ?
C7 C6 H6A 120.3 . . ?
C6 C7 C2 119.93(16) . . ?
C6 C7 C8 131.57(16) . . ?
C2 C7 C8 108.48(14) . . ?
C9 C8 C13 120.25(17) . . ?
C9 C8 C7 130.83(16) . . ?
C13 C8 C7 108.90(13) . . ?
C10 C9 C8 119.08(18) . . ?
C10 C9 H9A 120.5 . . ?
C8 C9 H9A 120.5 . . ?
C11 C10 C9 120.90(17) . . ?
C11 C10 H10A 119.6 . . ?
C9 C10 H10A 119.6 . . ?
C10 C11 C12 120.96(19) . . ?
C10 C11 H11A 119.5 . . ?
C12 C11 H11A 119.5 . . ?
C11 C12 C13 118.94(18) . . ?
C11 C12 H12A 120.5 . . ?
C13 C12 H12A 120.5 . . ?
C12 C13 C8 119.87(15) . . ?
C12 C13 C1 131.74(15) . . ?
C8 C13 C1 108.39(14) . . ?
C1 C14 C15A 128.3(2) . . ?
C1 C14 C15 127.90(16) . . ?
C15A C14 C15 103.8(2) . . ?
C1 C14 H14B 115.8 . . ?
C15A C14 H14B 115.8 . . ?
C15 C14 H14B 12.1 . . ?
C1 C14 H14A 116.2 . . ?
C15A C14 H14A 12.2 . . ?
C15 C14 H14A 115.9 . . ?
H14B C14 H14A 128.0 . . ?
C20 C15 C16 117.8(2) . . ?
C20 C15 C14 120.3(2) . . ?
C16 C15 C14 121.8(2) . . ?
C15 C16 C17 120.0(3) . . ?
C15 C16 H16A 120.0 . . ?
C17 C16 H16A 120.0 . . ?
C18 C17 C16 121.0(3) . . ?
C18 C17 H17A 119.5 . . ?
C16 C17 H17A 119.5 . . ?
C19 C18 C17 119.6(4) . . ?
C19 C18 H18A 120.2 . . ?
C17 C18 H18A 120.2 . . ?
C18 C19 C20 120.5(4) . . ?
C18 C19 H19A 119.8 . . ?
C20 C19 H19A 119.8 . . ?
C15 C20 C19 120.7(3) . . ?
C15 C20 H20A 119.7 . . ?
C19 C20 H20A 119.7 . . ?
C16A C15A C20A 120.0 . . ?
C16A C15A C14 116.7(3) . . ?
C20A C15A C14 123.3(3) . . ?
C16A C15A H14A 115.0 . . ?
C20A C15A H14A 119.8 . . ?
C14 C15A H14A 21.1 . . ?
C17A C16A C15A 120.0 . . ?
C17A C16A H16B 120.0 . . ?
C15A C16A H16B 120.0 . . ?
C18A C17A C16A 120.0 . . ?
C18A C17A H17B 120.0 . . ?
C16A C17A H17B 120.0 . . ?
C17A C18A C19A 120.0 . . ?
C17A C18A H18B 120.0 . . ?
C19A C18A H18B 120.0 . . ?
C18A C19A C20A 120.0 . . ?
C18A C19A H19B 120.0 . . ?
C20A C19A H19B 120.0 . . ?
C19A C20A C15A 120.0 . . ?
C19A C20A H20B 120.0 . . ?
C15A C20A H20B 120.0 . . ?
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
C1 C14 1.315(2) . ?
C1 C13 1.470(2) . ?
C1 C2 1.475(2) . ?
C2 C3 1.373(2) . ?
C2 C7 1.388(2) . ?
C3 C4 1.367(3) . ?
C3 H3A 0.9500 . ?
C4 C5 1.359(3) . ?
C4 H4A 0.9500 . ?
C5 C6 1.367(3) . ?
C5 H5A 0.9500 . ?
C6 C7 1.375(2) . ?
C6 H6A 0.9500 . ?
C7 C8 1.455(2) . ?
C8 C9 1.375(2) . ?
C8 C13 1.391(2) . ?
C9 C10 1.371(3) . ?
C9 H9A 0.9500 . ?
C10 C11 1.363(3) . ?
C10 H10A 0.9500 . ?
C11 C12 1.372(2) . ?
C11 H11A 0.9500 . ?
C12 C13 1.383(2) . ?
C12 H12A 0.9500 . ?
C14 C15A 1.419(4) . ?
C14 C15 1.457(3) . ?
C14 H14B 0.9500 . ?
C14 H14A 0.9300 . ?
C15 C20 1.358(4) . ?
C15 C16 1.362(3) . ?
C16 C17 1.379(6) . ?
C16 H16A 0.9500 . ?
C17 C18 1.337(6) . ?
C17 H17A 0.9500 . ?
C18 C19 1.317(6) . ?
C18 H18A 0.9500 . ?
C19 C20 1.388(5) . ?
C19 H19A 0.9500 . ?
C20 H20A 0.9500 . ?
C15A C16A 1.3900 . ?
C15A C20A 1.3900 . ?
C15A H14A 0.5470 . ?
C16A C17A 1.3900 . ?
C16A H16B 0.9500 . ?
C17A C18A 1.3900 . ?
C17A H17B 0.9500 . ?
C18A C19A 1.3900 . ?
C18A H18B 0.9500 . ?
C19A C20A 1.3900 . ?
C19A H19B 0.9500 . ?
C20A H20B 0.9500 . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 137231
