#------------------------------------------------------------------------------
#$Date: 2016-03-21 14:45:29 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178722 $
#$URL: svn://www.crystallography.net/cod/cif/4/08/33/4083372.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_4083372
loop_
_publ_author_name
'Albert, Joan'
'Bosque, Ramon'
'Cadena, Magali'
'D’Andrea, Lucía'
'Granell, Jaume'
'González, Asensio'
'Quirante, Josefina'
'Calvis, Carmen'
'Messeguer, Ramon'
'Badía, Josefa'
'Baldomà, Laura'
'Calvet, Teresa'
'Font-Bardia, Mercè'
_publ_section_title
;
 A New Family of Doubly Cyclopalladated Diimines. A Remarkable Effect of
 the Linker between the Metalated Units on Their Cytotoxicity
;
_journal_issue                   11
_journal_name_full               Organometallics
_journal_page_first              2862
_journal_paper_doi               10.1021/om500382f
_journal_volume                  33
_journal_year                    2014
_chemical_formula_moiety         'C28 H18 D10 Cl2 N4 O2 Pd2, 2(C D Cl3)'
_chemical_formula_sum            'C30 H18 Cl8 D12 N4 O2 Pd2'
_chemical_formula_weight         987.05
_chemical_name_systematic
;
 ?
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90
_cell_angle_beta                 104.60(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   11.573(6)
_cell_length_b                   8.563(3)
_cell_length_c                   19.512(8)
_cell_measurement_reflns_used    253
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      30
_cell_measurement_theta_min      3
_cell_volume                     1871.2(14)
_computing_cell_refinement       'AUTOMAR (Claudio Klein, 2007)'
_computing_data_collection       'MARXDS (Claudio Klein, 2005)'
_computing_data_reduction        'MARSCALE (Claudio Klein, 2007)'
_computing_molecular_graphics    'ORTEP (Brueggermann and Smith, 1990)'
_computing_publication_material  'PLATON (Spek, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.959
_diffrn_measured_fraction_theta_max 0.875
_diffrn_measurement_device_type  'MAR345 with image plate detector'
_diffrn_measurement_method       'phi 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  0.0542
_diffrn_reflns_av_sigmaI/netI    0.0725
_diffrn_reflns_Laue_measured_fraction_full 0.959
_diffrn_reflns_Laue_measured_fraction_max 0.875
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            19920
_diffrn_reflns_point_group_measured_fraction_full 0.959
_diffrn_reflns_point_group_measured_fraction_max 0.875
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         32.408
_diffrn_reflns_theta_min         2.612
_exptl_absorpt_coefficient_mu    1.566
_exptl_crystal_density_diffrn    1.752
_exptl_crystal_description       prism
_exptl_crystal_F_000             964
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         1.018
_refine_diff_density_min         -0.893
_refine_diff_density_rms         0.094
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.174
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         5876
_refine_ls_number_restraints     24
_refine_ls_restrained_S_all      1.173
_refine_ls_R_factor_all          0.1075
_refine_ls_R_factor_gt           0.0672
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 w=1/[σ²(Fo²)+(0.0658P)²+0.4805P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1571
_refine_ls_wR_factor_ref         0.1752
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4182
_reflns_number_total             5876
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            om500382f_si_003.cif
_cod_data_source_block           jalm62a
_cod_depositor_comments
'Adding full bibliography for 4083372--4083374.cif.'
_cod_database_code               4083372
#BEGIN Tags that were not found in dictionaries:
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
#END Tags that were not found in dictionaries
loop_
_space_group_symop_operation_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
Pd1 Pd 0.27513(3) 0.85119(4) 0.56384(2) 0.05111(13) Uani 1 1 d . U
Cl1 Cl 0.19703(11) 0.94787(17) 0.65914(7) 0.0667(3) Uani 1 1 d . U
O1 O 0.5774(4) 0.6260(5) 0.4115(3) 0.0866(13) Uani 1 1 d D .
N1 N 0.1174(4) 0.8618(5) 0.4888(2) 0.0585(9) Uani 1 1 d . .
N2 N 0.4384(3) 0.8237(4) 0.6345(2) 0.0487(8) Uani 1 1 d . .
C1 C 0.3341(4) 0.7712(6) 0.4820(2) 0.0574(11) Uani 1 1 d . .
C2 C 0.4480(4) 0.7261(6) 0.4796(3) 0.0594(11) Uani 1 1 d D .
H2 H 0.506(4) 0.731(7) 0.5199(17) 0.071 Uiso 1 1 d D U
C3 C 0.4694(5) 0.6722(6) 0.4166(3) 0.0658(13) Uani 1 1 d . .
C4 C 0.3779(7) 0.6607(7) 0.3584(4) 0.0771(15) Uani 1 1 d D .
H4 H 0.384(6) 0.616(8) 0.318(2) 0.093 Uiso 1 1 d D U
C5 C 0.2614(6) 0.7055(8) 0.3580(3) 0.0711(14) Uani 1 1 d D .
H5 H 0.206(4) 0.696(7) 0.3167(19) 0.085 Uiso 1 1 d D U
C6 C 0.2413(4) 0.7616(6) 0.4205(3) 0.0596(11) Uani 1 1 d . .
C7 C 0.1244(5) 0.8150(7) 0.4267(3) 0.0685(13) Uani 1 1 d D .
H7 H 0.060(4) 0.814(7) 0.390(2) 0.082 Uiso 1 1 d D U
C8 C 0.0036(4) 0.9100(6) 0.4988(3) 0.0565(10) Uani 1 1 d D .
H8A H -0.050(4) 0.876(5) 0.4596(14) 0.068 Uiso 1 1 d D U
H8 H -0.008(4) 0.866(5) 0.5387(13) 0.068 Uiso 1 1 d D U
C9 C 0.6783(6) 0.6536(9) 0.4677(4) 0.095(2) Uani 1 1 d D .
H9 H 0.688(4) 0.7583(13) 0.473(2) 0.142 Uiso 1 1 d D U
H9B H 0.666(3) 0.608(7) 0.5071(10) 0.142 Uiso 1 1 d D U
H9A H 0.7422(13) 0.610(7) 0.4557(18) 0.142 Uiso 1 1 d D U
C10 C 0.5323(5) 0.9158(7) 0.6338(3) 0.0677(13) Uani 1 1 d D .
D10 D 0.525(5) 0.988(5) 0.600(2) 0.081 Uiso 1 1 d D U
C11 C 0.6372(5) 0.9057(8) 0.6852(4) 0.0789(16) Uani 1 1 d D .
D11 D 0.700(4) 0.967(7) 0.684(4) 0.095 Uiso 1 1 d D U
C12 C 0.6489(6) 0.7941(9) 0.7335(4) 0.0853(18) Uani 1 1 d D .
D12 D 0.7270(19) 0.784(8) 0.756(3) 0.102 Uiso 1 1 d D U
C13 C 0.5559(6) 0.6912(9) 0.7332(3) 0.0779(16) Uani 1 1 d D .
D13 D 0.563(6) 0.611(6) 0.764(3) 0.094 Uiso 1 1 d D U
C14 C 0.4506(5) 0.7130(7) 0.6829(3) 0.0672(13) Uani 1 1 d . .
D14 D 0.377(6) 0.645(7) 0.677(3) 0.081 Uiso 1 1 d . U
Cl2 Cl -0.0525(3) 1.0251(4) 0.9059(2) 0.1646(12) Uani 1 1 d . .
Cl3 Cl -0.0400(2) 1.0107(4) 0.76133(14) 0.1357(9) Uani 1 1 d . .
Cl4 Cl 0.1241(2) 1.1944(3) 0.86054(15) 0.1248(8) Uani 1 1 d . .
C15 C -0.0194(6) 1.1245(8) 0.8364(4) 0.0795(17) Uani 1 1 d . .
D15 D -0.072(6) 1.201(9) 0.829(4) 0.095 Uiso 1 1 d . U
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'
Cl Cl 0.1484 0.1585 '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'
Pd Pd -0.9988 1.0072 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
D D 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
C1 Pd1 N1 82.3(2) . .
C1 Pd1 N2 93.17(18) . .
N1 Pd1 N2 174.76(16) . .
C1 Pd1 Cl1 177.86(14) . .
N1 Pd1 Cl1 95.59(14) . .
N2 Pd1 Cl1 88.96(12) . .
C3 O1 C9 120.0(5) . .
C7 N1 C8 119.3(4) . .
C7 N1 Pd1 113.8(4) . .
C8 N1 Pd1 126.9(3) . .
C14 N2 C10 119.1(4) . .
C14 N2 Pd1 118.5(3) . .
C10 N2 Pd1 122.3(3) . .
C2 C1 C6 119.1(5) . .
C2 C1 Pd1 129.7(4) . .
C6 C1 Pd1 111.2(4) . .
C1 C2 C3 120.3(5) . .
C1 C2 H2 118(4) . .
C3 C2 H2 122(4) . .
O1 C3 C4 117.8(5) . .
O1 C3 C2 122.7(5) . .
C4 C3 C2 119.4(5) . .
C3 C4 C5 122.4(6) . .
C3 C4 H4 124(4) . .
C5 C4 H4 113(4) . .
C6 C5 C4 117.8(5) . .
C6 C5 H5 125(4) . .
C4 C5 H5 117(4) . .
C5 C6 C1 120.9(5) . .
C5 C6 C7 123.1(5) . .
C1 C6 C7 116.0(5) . .
N1 C7 C6 116.8(5) . .
N1 C7 H7 121(4) . .
C6 C7 H7 122(4) . .
N1 C8 C8 110.4(5) . 3_576
N1 C8 H8A 104(4) . .
C8 C8 H8A 108(3) 3_576 .
N1 C8 H8 109(4) . .
C8 C8 H8 112(3) 3_576 .
H8A C8 H8 112.2(17) . .
O1 C9 H9 108.1(10) . .
O1 C9 H9B 108.3(11) . .
H9 C9 H9B 111.4(12) . .
O1 C9 H9A 107.5(10) . .
H9 C9 H9A 110.9(12) . .
H9B C9 H9A 110.5(12) . .
N2 C10 C11 121.7(5) . .
N2 C10 D10 119(4) . .
C11 C10 D10 119(4) . .
C12 C11 C10 118.6(6) . .
C12 C11 D11 120(4) . .
C10 C11 D11 121(4) . .
C11 C12 C13 120.9(6) . .
C11 C12 D12 109(5) . .
C13 C12 D12 128(5) . .
C14 C13 C12 117.7(6) . .
C14 C13 D13 120(5) . .
C12 C13 D13 123(4) . .
N2 C14 C13 121.7(6) . .
N2 C14 D14 113(3) . .
C13 C14 D14 125(3) . .
Cl4 C15 Cl2 110.4(4) . .
Cl4 C15 Cl3 110.3(4) . .
Cl2 C15 Cl3 112.2(4) . .
Cl4 C15 D15 112(5) . .
Cl2 C15 D15 102(5) . .
Cl3 C15 D15 110(5) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Pd1 C1 2.008(5) .
Pd1 N1 2.034(4) .
Pd1 N2 2.052(4) .
Pd1 Cl1 2.4099(16) .
O1 C3 1.338(7) .
O1 C9 1.407(8) .
N1 C7 1.297(7) .
N1 C8 1.440(7) .
N2 C14 1.320(7) .
N2 C10 1.346(7) .
C1 C2 1.386(7) .
C1 C6 1.396(7) .
C2 C3 1.394(7) .
C2 H2 0.899(10) .
C3 C4 1.347(9) .
C4 C5 1.399(9) .
C4 H4 0.900(10) .
C5 C6 1.383(8) .
C5 H5 0.901(10) .
C6 C7 1.462(8) .
C7 H7 0.899(10) .
C8 C8 1.544(11) 3_576
C8 H8A 0.903(10) .
C8 H8 0.903(10) .
C9 H9 0.906(7) .
C9 H9B 0.905(7) .
C9 H9A 0.909(7) .
C10 C11 1.368(8) .
C10 D10 0.901(10) .
C11 C12 1.325(10) .
C11 D11 0.898(10) .
C12 C13 1.389(10) .
C12 D12 0.903(10) .
C13 C14 1.371(8) .
C13 D13 0.903(10) .
C14 D14 1.01(6) .
Cl2 C15 1.723(8) .
Cl3 C15 1.726(7) .
Cl4 C15 1.715(7) .
C15 D15 0.88(7) .
