#------------------------------------------------------------------------------
#$Date: 2019-10-16 03:14:49 +0300 (Wed, 16 Oct 2019) $
#$Revision: 219371 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/12/43/7124320.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_7124320
loop_
_publ_author_name
'Elakkat, Vijayanath'
'Chang, Chu-Jun'
'Chen, Jun-Yu'
'Fang, Yung-Cheng'
'Shen, Chia-Rui'
'LIU, Ling-Kang'
'Lu, Norman'
_publ_section_title
;
 The first two examples of halogen bonding with a sigma hole-donating
 fluorine in Csp3-F…Osp3 interaction from polyfluorinated
 trans-dihalo-palladium(II) di-substituted pyridine complexes
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/C9CC06731K
_journal_year                    2019
_chemical_formula_moiety         'C18 H18 Cl2 F8 N2 O2 Pd'
_chemical_formula_sum            'C18 H18 Cl2 F8 N2 O2 Pd'
_chemical_formula_weight         623.64
_chemical_melting_point          411.15
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2019-08-23 deposited with the CCDC.    2019-10-15 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 109.6250(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.0691(2)
_cell_length_b                   18.6278(5)
_cell_length_c                   8.7985(3)
_cell_measurement_reflns_used    6271
_cell_measurement_temperature    100.0(2)
_cell_measurement_theta_max      27.12
_cell_measurement_theta_min      2.19
_cell_volume                     1091.30(6)
_computing_cell_refinement       'SAINT V8.35A (Bruker AXS Inc., 2015)'
_computing_data_collection       'Bruker Instrument Service v2012.12.0.3'
_computing_data_reduction        'SAINT V8.35A (Bruker AXS Inc., 2015)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 740)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'XT, VERSION 2014/4'
_diffrn_ambient_temperature      100.0(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0397
_diffrn_reflns_av_unetI/netI     0.0318
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            11039
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         27.102
_diffrn_reflns_theta_min         2.187
_exptl_absorpt_coefficient_mu    1.182
_exptl_absorpt_correction_T_max  0.9705
_exptl_absorpt_correction_T_min  0.8436
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker SADABS, 1996'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.898
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             616
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Dimethyl sulfoxide, water'
_exptl_crystal_size_max          0.440
_exptl_crystal_size_mid          0.400
_exptl_crystal_size_min          0.060
_refine_diff_density_max         0.453
_refine_diff_density_min         -0.600
_refine_diff_density_rms         0.072
_refine_ls_extinction_coef       0.0017(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     152
_refine_ls_number_reflns         2398
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0239
_refine_ls_R_factor_gt           0.0211
_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)+(0.0137P)²+0.6841P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0479
_refine_ls_wR_factor_ref         0.0498
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2195
_reflns_number_total             2398
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c9cc06731k2.cif
_cod_data_source_block           i16265
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'none' was changed to '?' - the
value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas 
;
_cod_database_code               7124320
_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.
;
_shelxl_version_number           2013-4
loop_
_space_group_symop_operation_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
Pd1 Pd 0.5000 0.5000 1.0000 0.00780(7) Uani 1 2 d S . P
Cl1 Cl 0.77495(6) 0.56218(2) 1.16485(5) 0.01241(11) Uani 1 1 d . . .
F1 F 0.16602(17) 0.62555(6) -0.04913(13) 0.0181(2) Uani 1 1 d . . .
F2 F 0.07357(17) 0.73832(6) -0.08363(13) 0.0195(3) Uani 1 1 d . . .
F3 F 0.43022(19) 0.71022(7) -0.12084(15) 0.0262(3) Uani 1 1 d . . .
F4 F 0.45122(17) 0.78113(6) 0.08116(14) 0.0213(3) Uani 1 1 d . . .
O1 O 0.30192(18) 0.64571(7) 0.28297(15) 0.0113(3) Uani 1 1 d . . .
N1 N 0.5549(2) 0.53722(8) 0.80331(18) 0.0096(3) Uani 1 1 d . . .
C1 C 0.4122(3) 0.57321(10) 0.6895(2) 0.0101(4) Uani 1 1 d . . .
H1 H 0.2860 0.5802 0.7036 0.012 Uiso 1 1 calc R U .
C2 C 0.4400(3) 0.60077(10) 0.5520(2) 0.0102(4) Uani 1 1 d . . .
C3 C 0.6246(3) 0.58880(10) 0.5314(2) 0.0116(4) Uani 1 1 d . . .
H3 H 0.6494 0.6063 0.4385 0.014 Uiso 1 1 calc R U .
C4 C 0.7708(3) 0.55110(10) 0.6485(2) 0.0127(4) Uani 1 1 d . . .
H4 H 0.8972 0.5423 0.6360 0.015 Uiso 1 1 calc R U .
C5 C 0.7339(3) 0.52619(10) 0.7835(2) 0.0110(4) Uani 1 1 d . . .
H5 H 0.8362 0.5008 0.8638 0.013 Uiso 1 1 calc R U .
C6 C 0.2737(3) 0.64311(10) 0.4354(2) 0.0130(4) Uani 1 1 d . . .
H6A H 0.1429 0.6204 0.4236 0.016 Uiso 1 1 calc R U .
H6B H 0.2726 0.6924 0.4770 0.016 Uiso 1 1 calc R U .
C7 C 0.1645(3) 0.69345(10) 0.1769(2) 0.0116(4) Uani 1 1 d . . .
H7A H 0.1837 0.7427 0.2221 0.014 Uiso 1 1 calc R U .
H7B H 0.0249 0.6783 0.1607 0.014 Uiso 1 1 calc R U .
C8 C 0.2039(3) 0.69182(10) 0.0193(2) 0.0124(4) Uani 1 1 d . . .
C9 C 0.4170(3) 0.71220(11) 0.0300(2) 0.0160(4) Uani 1 1 d . . .
H9 H 0.5175 0.6792 0.1045 0.019 Uiso 1 1 calc R 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'
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'
F F 0.0171 0.0103 '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
N1 Pd1 N1 180.00(7) 3_667 .
N1 Pd1 Cl1 90.15(4) 3_667 3_667
N1 Pd1 Cl1 89.85(4) . 3_667
N1 Pd1 Cl1 89.85(4) 3_667 .
N1 Pd1 Cl1 90.15(4) . .
Cl1 Pd1 Cl1 180.0 3_667 .
C7 O1 C6 111.19(13) . .
C1 N1 C5 118.90(15) . .
C1 N1 Pd1 119.97(11) . .
C5 N1 Pd1 121.13(12) . .
N1 C1 C2 123.06(16) . .
N1 C1 H1 118.5 . .
C2 C1 H1 118.5 . .
C1 C2 C3 117.83(16) . .
C1 C2 C6 118.88(15) . .
C3 C2 C6 123.28(16) . .
C4 C3 C2 118.90(16) . .
C4 C3 H3 120.5 . .
C2 C3 H3 120.5 . .
C5 C4 C3 120.18(16) . .
C5 C4 H4 119.9 . .
C3 C4 H4 119.9 . .
N1 C5 C4 121.12(17) . .
N1 C5 H5 119.4 . .
C4 C5 H5 119.4 . .
O1 C6 C2 109.71(14) . .
O1 C6 H6A 109.7 . .
C2 C6 H6A 109.7 . .
O1 C6 H6B 109.7 . .
C2 C6 H6B 109.7 . .
H6A C6 H6B 108.2 . .
O1 C7 C8 107.29(14) . .
O1 C7 H7A 110.3 . .
C8 C7 H7A 110.3 . .
O1 C7 H7B 110.3 . .
C8 C7 H7B 110.3 . .
H7A C7 H7B 108.5 . .
F1 C8 F2 107.10(14) . .
F1 C8 C7 110.91(15) . .
F2 C8 C7 107.87(14) . .
F1 C8 C9 107.23(14) . .
F2 C8 C9 108.40(15) . .
C7 C8 C9 115.04(15) . .
F4 C9 F3 106.66(15) . .
F4 C9 C8 108.56(15) . .
F3 C9 C8 108.84(16) . .
F4 C9 H9 110.9 . .
F3 C9 H9 110.9 . .
C8 C9 H9 110.9 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Pd1 N1 2.0192(14) 3_667
Pd1 N1 2.0192(14) .
Pd1 Cl1 2.3086(4) 3_667
Pd1 Cl1 2.3086(4) .
F1 C8 1.360(2) .
F2 C8 1.363(2) .
F3 C9 1.361(2) .
F4 C9 1.355(2) .
O1 C7 1.413(2) .
O1 C6 1.422(2) .
N1 C1 1.338(2) .
N1 C5 1.350(2) .
C1 C2 1.388(2) .
C1 H1 0.9500 .
C2 C3 1.394(2) .
C2 C6 1.499(3) .
C3 C4 1.381(3) .
C3 H3 0.9500 .
C4 C5 1.379(3) .
C4 H4 0.9500 .
C5 H5 0.9500 .
C6 H6A 0.9900 .
C6 H6B 0.9900 .
C7 C8 1.503(2) .
C7 H7A 0.9900 .
C7 H7B 0.9900 .
C8 C9 1.526(3) .
C9 H9 1.0000 .
