#------------------------------------------------------------------------------
#$Date: 2016-02-16 22:30:59 +0200 (Tue, 16 Feb 2016) $
#$Revision: 176467 $
#$URL: svn://www.crystallography.net/cod/cif/4/11/02/4110259.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_4110259
loop_
_publ_author_name
'Sriparna Ray'
'Renu Mohan'
'Jay K. Singh'
'Manoja K. Samantaray'
'Mobin M. Shaikh'
'Dulal Panda'
'Prasenjit Ghosh'
_publ_section_title
;
 Anticancer and Antimicrobial Metallopharmaceutical Agents Based on
 Palladium, Gold, and Silver N-Heterocyclic Carbene Complexes
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              15042
_journal_page_last               15053
_journal_paper_doi               10.1021/ja075889z
_journal_volume                  129
_journal_year                    2007
_chemical_formula_sum            'C14 H18 Cl N2 Pd0.5'
_chemical_formula_weight         302.95
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/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                 115.070(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.2107(6)
_cell_length_b                   13.9758(6)
_cell_length_c                   10.6444(6)
_cell_measurement_reflns_used    5895
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      32.1331
_cell_measurement_theta_min      3.5733
_cell_volume                     1375.88(15)
_computing_cell_refinement       'CrysAlis RED, Oxford Diffraction Ltd.,'
_computing_data_collection       'CrysAlis CCD, Oxford Diffraction Ltd.,'
_computing_data_reduction        'CrysAlis RED, Oxford Diffraction Ltd.,'
_computing_molecular_graphics    Ortep3
_computing_publication_material  Shelx97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 15.9948
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0389
_diffrn_reflns_av_sigmaI/netI    0.0327
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            8819
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         3.60
_exptl_absorpt_coefficient_mu    0.892
_exptl_absorpt_correction_T_max  0.7882
_exptl_absorpt_correction_T_min  0.7453
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.29.2 (release 20-01-2006 CrysAlis171 .NET)
(compiled Jan 20 2006,12:36:28)
empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.463
_exptl_crystal_description       block
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.28
_refine_diff_density_max         1.854
_refine_diff_density_min         -0.576
_refine_diff_density_rms         0.135
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.999
_refine_ls_hydrogen_treatment    riding
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2424
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.999
_refine_ls_R_factor_all          0.0575
_refine_ls_R_factor_gt           0.0471
_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)+(0.0974P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1206
_refine_ls_wR_factor_ref         0.1279
_reflns_number_gt                1940
_reflns_number_total             2424
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja075889zsi20070806_105215.cif
_cod_data_source_block           pg077
_cod_original_cell_volume        1375.88(13)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_original_formula_sum        'C14 H18 Cl N2 Pd0.50'
_cod_database_code               4110259
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
Pd1 Pd 1.0000 0.0000 1.0000 0.0285(2) Uani 1 2 d S
Cl1 Cl 1.18388(11) 0.02575(8) 1.22004(10) 0.0370(3) Uani 1 1 d .
N1 N 1.1609(3) 0.1380(2) 0.8815(3) 0.0302(7) Uani 1 1 d .
N2 N 1.0258(3) 0.2103(2) 0.9600(3) 0.0309(7) Uani 1 1 d .
C1 C 1.0673(4) 0.1219(3) 0.9388(4) 0.0304(8) Uani 1 1 d .
C2 C 1.0922(4) 0.2803(3) 0.9174(4) 0.0347(9) Uani 1 1 d .
H2 H 1.0803 0.3460 0.9214 0.042 Uiso 1 1 calc R
C3 C 1.1774(4) 0.2357(3) 0.8689(4) 0.0343(9) Uani 1 1 d .
H3 H 1.2366 0.2647 0.8335 0.041 Uiso 1 1 calc R
C4 C 1.2322(4) 0.0620(3) 0.8298(4) 0.0334(9) Uani 1 1 d .
C5 C 1.3035(5) -0.0106(3) 0.9445(5) 0.0411(11) Uani 1 1 d .
H5A H 1.3521 -0.0580 0.9145 0.062 Uiso 1 1 calc R
H5B H 1.2312 -0.0409 0.9662 0.062 Uiso 1 1 calc R
H5C H 1.3723 0.0212 1.0256 0.062 Uiso 1 1 calc R
C6 C 1.1174(5) 0.0156(3) 0.7020(5) 0.0432(11) Uani 1 1 d .
H6A H 1.0737 0.0632 0.6314 0.065 Uiso 1 1 calc R
H6B H 1.0449 -0.0127 0.7253 0.065 Uiso 1 1 calc R
H6C H 1.1609 -0.0330 0.6684 0.065 Uiso 1 1 calc R
C7 C 1.3456(4) 0.1092(3) 0.7934(4) 0.0428(10) Uani 1 1 d .
H7A H 1.3000 0.1554 0.7210 0.064 Uiso 1 1 calc R
H7B H 1.3927 0.0615 0.7623 0.064 Uiso 1 1 calc R
H7C H 1.4158 0.1408 0.8739 0.064 Uiso 1 1 calc R
C8 C 0.9279(4) 0.2305(3) 1.0249(4) 0.0341(9) Uani 1 1 d .
H8A H 0.9730 0.2774 1.0978 0.041 Uiso 1 1 calc R
H8B H 0.9146 0.1724 1.0679 0.041 Uiso 1 1 calc R
C9 C 0.7805(4) 0.2678(3) 0.9252(4) 0.0357(9) Uani 1 1 d .
C10 C 0.7048(5) 0.2257(3) 0.7976(4) 0.0417(10) Uani 1 1 d .
H10 H 0.7457 0.1750 0.7702 0.050 Uiso 1 1 calc R
C11 C 0.5677(5) 0.2583(4) 0.7095(5) 0.0523(12) Uani 1 1 d .
H11 H 0.5192 0.2308 0.6223 0.063 Uiso 1 1 calc R
C12 C 0.5035(5) 0.3304(4) 0.7497(6) 0.0532(12) Uani 1 1 d .
H12 H 0.4106 0.3506 0.6915 0.064 Uiso 1 1 calc R
C13 C 0.5770(6) 0.3727(3) 0.8763(6) 0.0560(13) Uani 1 1 d .
H13 H 0.5340 0.4221 0.9038 0.067 Uiso 1 1 calc R
C14 C 0.7157(5) 0.3424(3) 0.9644(5) 0.0440(11) Uani 1 1 d .
H14 H 0.7652 0.3721 1.0498 0.053 Uiso 1 1 calc R
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'
Cl Cl 0.1484 0.1585 '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'
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
C1 Pd1 C1 180.00(12) . 3_757
C1 Pd1 Cl1 92.57(10) . 3_757
C1 Pd1 Cl1 87.43(10) 3_757 3_757
C1 Pd1 Cl1 87.43(10) . .
C1 Pd1 Cl1 92.57(10) 3_757 .
Cl1 Pd1 Cl1 180.0 3_757 .
C1 N1 C3 110.2(3) . .
C1 N1 C4 125.9(3) . .
C3 N1 C4 123.8(3) . .
C1 N2 C2 111.2(3) . .
C1 N2 C8 125.4(3) . .
C2 N2 C8 123.4(3) . .
N1 C1 N2 104.7(3) . .
N1 C1 Pd1 132.8(3) . .
N2 C1 Pd1 122.4(3) . .
C3 C2 N2 106.8(3) . .
C3 C2 H2 126.6 . .
N2 C2 H2 126.6 . .
C2 C3 N1 107.2(3) . .
C2 C3 H3 126.4 . .
N1 C3 H3 126.4 . .
C6 C4 C5 111.2(3) . .
C6 C4 N1 108.5(3) . .
C5 C4 N1 108.5(3) . .
C6 C4 C7 109.9(3) . .
C5 C4 C7 109.8(3) . .
N1 C4 C7 108.8(3) . .
C4 C5 H5A 109.5 . .
C4 C5 H5B 109.5 . .
H5A C5 H5B 109.5 . .
C4 C5 H5C 109.5 . .
H5A C5 H5C 109.5 . .
H5B C5 H5C 109.5 . .
C4 C6 H6A 109.5 . .
C4 C6 H6B 109.5 . .
H6A C6 H6B 109.5 . .
C4 C6 H6C 109.5 . .
H6A C6 H6C 109.5 . .
H6B C6 H6C 109.5 . .
C4 C7 H7A 109.5 . .
C4 C7 H7B 109.5 . .
H7A C7 H7B 109.5 . .
C4 C7 H7C 109.5 . .
H7A C7 H7C 109.5 . .
H7B C7 H7C 109.5 . .
N2 C8 C9 114.2(3) . .
N2 C8 H8A 108.7 . .
C9 C8 H8A 108.7 . .
N2 C8 H8B 108.7 . .
C9 C8 H8B 108.7 . .
H8A C8 H8B 107.6 . .
C10 C9 C14 118.4(4) . .
C10 C9 C8 121.2(3) . .
C14 C9 C8 120.3(4) . .
C9 C10 C11 120.6(4) . .
C9 C10 H10 119.7 . .
C11 C10 H10 119.7 . .
C12 C11 C10 120.6(5) . .
C12 C11 H11 119.7 . .
C10 C11 H11 119.7 . .
C11 C12 C13 119.4(4) . .
C11 C12 H12 120.3 . .
C13 C12 H12 120.3 . .
C12 C13 C14 120.6(4) . .
C12 C13 H13 119.7 . .
C14 C13 H13 119.7 . .
C9 C14 C13 120.3(4) . .
C9 C14 H14 119.9 . .
C13 C14 H14 119.9 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Pd1 C1 2.044(4) .
Pd1 C1 2.044(4) 3_757
Pd1 Cl1 2.3268(10) 3_757
Pd1 Cl1 2.3268(10) .
N1 C1 1.353(5) .
N1 C3 1.389(5) .
N1 C4 1.517(5) .
N2 C1 1.355(5) .
N2 C2 1.372(5) .
N2 C8 1.463(5) .
C2 C3 1.338(5) .
C2 H2 0.9300 .
C3 H3 0.9300 .
C4 C6 1.514(6) .
C4 C5 1.516(6) .
C4 C7 1.518(5) .
C5 H5A 0.9600 .
C5 H5B 0.9600 .
C5 H5C 0.9600 .
C6 H6A 0.9600 .
C6 H6B 0.9600 .
C6 H6C 0.9600 .
C7 H7A 0.9600 .
C7 H7B 0.9600 .
C7 H7C 0.9600 .
C8 C9 1.520(5) .
C8 H8A 0.9700 .
C8 H8B 0.9700 .
C9 C10 1.378(6) .
C9 C14 1.390(6) .
C10 C11 1.391(6) .
C10 H10 0.9300 .
C11 C12 1.366(7) .
C11 H11 0.9300 .
C12 C13 1.368(7) .
C12 H12 0.9300 .
C13 C14 1.393(7) .
C13 H13 0.9300 .
C14 H14 0.9300 .
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
C3 N1 C1 N2 0.5(4) .
C4 N1 C1 N2 -176.1(3) .
C3 N1 C1 Pd1 -175.4(3) .
C4 N1 C1 Pd1 7.9(5) .
C2 N2 C1 N1 -0.2(4) .
C8 N2 C1 N1 -177.8(3) .
C2 N2 C1 Pd1 176.3(2) .
C8 N2 C1 Pd1 -1.3(5) .
C1 Pd1 C1 N1 -131(84) 3_757
Cl1 Pd1 C1 N1 -87.2(3) 3_757
Cl1 Pd1 C1 N1 92.8(3) .
C1 Pd1 C1 N2 54(89) 3_757
Cl1 Pd1 C1 N2 97.4(3) 3_757
Cl1 Pd1 C1 N2 -82.6(3) .
C1 N2 C2 C3 -0.2(4) .
C8 N2 C2 C3 177.4(3) .
N2 C2 C3 N1 0.5(4) .
C1 N1 C3 C2 -0.7(4) .
C4 N1 C3 C2 176.1(3) .
C1 N1 C4 C6 68.7(4) .
C3 N1 C4 C6 -107.5(4) .
C1 N1 C4 C5 -52.2(5) .
C3 N1 C4 C5 131.6(4) .
C1 N1 C4 C7 -171.7(3) .
C3 N1 C4 C7 12.1(5) .
C1 N2 C8 C9 -109.3(4) .
C2 N2 C8 C9 73.3(5) .
N2 C8 C9 C10 45.2(5) .
N2 C8 C9 C14 -138.2(4) .
C14 C9 C10 C11 1.0(6) .
C8 C9 C10 C11 177.6(4) .
C9 C10 C11 C12 -2.3(7) .
C10 C11 C12 C13 2.0(7) .
C11 C12 C13 C14 -0.5(7) .
C10 C9 C14 C13 0.5(6) .
C8 C9 C14 C13 -176.2(4) .
C12 C13 C14 C9 -0.8(7) .
