#------------------------------------------------------------------------------
#$Date: 2019-10-16 03:14:49 +0300 (Wed, 16 Oct 2019) $
#$Revision: 219371 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/12/43/7124321.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_7124321
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 Br2 F8 N2 O2 Pd'
_chemical_formula_sum            'C18 H18 Br2 F8 N2 O2 Pd'
_chemical_formula_weight         712.56
_chemical_melting_point          414.15
_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   difmap
_audit_creation_method           SHELXL-2016/6
_audit_update_record
;
2019-08-23 deposited with the CCDC.    2019-10-15 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 110.215(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.2992(3)
_cell_length_b                   18.6059(7)
_cell_length_c                   8.7965(4)
_cell_measurement_reflns_used    9029
_cell_measurement_temperature    100.0(2)
_cell_measurement_theta_max      27.25
_cell_measurement_theta_min      2.7
_cell_volume                     1121.05(8)
_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-2016/6 (Sheldrick, 2016)'
_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  0.0409
_diffrn_reflns_av_unetI/netI     0.0169
_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            27252
_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         27.099
_diffrn_reflns_theta_min         2.189
_exptl_absorpt_coefficient_mu    4.477
_exptl_absorpt_correction_T_max  0.9705
_exptl_absorpt_correction_T_min  0.713
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker SADABS, 1996'
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    2.111
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             688
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Dimethyl sulfoxide, Water'
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.160
_refine_diff_density_max         0.411
_refine_diff_density_min         -0.704
_refine_diff_density_rms         0.064
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_matrix_type           full
_refine_ls_number_parameters     178
_refine_ls_number_reflns         2473
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.081
_refine_ls_R_factor_all          0.0163
_refine_ls_R_factor_gt           0.0153
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0122P)²+0.9744P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0370
_refine_ls_wR_factor_ref         0.0373
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2394
_reflns_number_total             2473
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c9cc06731k2.cif
_cod_data_source_block           i16264
_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               7124321
_shelx_shelxl_version_number     2016/6
_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.
;
_shelx_estimated_absorpt_t_min   0.413
_shelx_estimated_absorpt_t_max   0.534
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 0.500000 0.500000 1.000000 0.00860(5) Uani 1 2 d S . P
Br1 Br 0.78386(2) 0.56560(2) 1.17324(2) 0.01281(5) Uani 1 1 d . . .
F1 F 0.08337(15) 0.74066(6) -0.08384(12) 0.0192(2) Uani 1 1 d . . .
F2 F 0.17771(15) 0.62858(5) -0.04384(12) 0.0192(2) Uani 1 1 d . . .
F3 F 0.44777(16) 0.78627(6) 0.08041(13) 0.0210(2) Uani 1 1 d . . .
F4 F 0.43060(18) 0.71319(6) -0.11738(14) 0.0270(3) Uani 1 1 d . . .
O1 O 0.30429(16) 0.64904(6) 0.28581(14) 0.0123(2) Uani 1 1 d . . .
N1 N 0.55005(19) 0.53741(7) 0.80269(16) 0.0108(3) Uani 1 1 d . . .
C1 C 0.4124(2) 0.57560(8) 0.6911(2) 0.0111(3) Uani 1 1 d . . .
H1 H 0.293(3) 0.5820(11) 0.712(2) 0.013 Uiso 1 1 d . U .
C2 C 0.4395(2) 0.60361(8) 0.5547(2) 0.0110(3) Uani 1 1 d . . .
C3 C 0.6159(2) 0.59048(9) 0.5320(2) 0.0123(3) Uani 1 1 d . . .
H3 H 0.636(3) 0.6082(11) 0.437(2) 0.015 Uiso 1 1 d . U .
C4 C 0.7565(2) 0.55036(9) 0.6469(2) 0.0136(3) Uani 1 1 d . . .
H4 H 0.877(3) 0.5408(11) 0.634(2) 0.016 Uiso 1 1 d . U .
C5 C 0.7213(2) 0.52491(9) 0.7810(2) 0.0121(3) Uani 1 1 d . . .
H5 H 0.813(3) 0.4988(10) 0.858(3) 0.014 Uiso 1 1 d . U .
C6 C 0.2796(2) 0.64784(9) 0.4392(2) 0.0128(3) Uani 1 1 d . . .
H6A H 0.289(3) 0.6960(11) 0.479(2) 0.015 Uiso 1 1 d . U .
H6B H 0.154(3) 0.6273(11) 0.428(2) 0.015 Uiso 1 1 d . U .
C7 C 0.1741(2) 0.69788(9) 0.1795(2) 0.0123(3) Uani 1 1 d . . .
H7A H 0.038(3) 0.6840(11) 0.158(2) 0.015 Uiso 1 1 d . U .
H7B H 0.199(3) 0.7456(11) 0.219(2) 0.015 Uiso 1 1 d . U .
C8 C 0.2122(2) 0.69554(9) 0.0223(2) 0.0129(3) Uani 1 1 d . . .
C9 C 0.4173(3) 0.71676(9) 0.0326(2) 0.0163(3) Uani 1 1 d . . .
H9 H 0.514(3) 0.6861(11) 0.106(3) 0.020 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'
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'
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'
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 Br1 89.86(4) . .
N1 Pd1 Br1 90.14(4) 3_667 .
N1 Pd1 Br1 90.14(4) . 3_667
N1 Pd1 Br1 89.86(4) 3_667 3_667
Br1 Pd1 Br1 180.0 . 3_667
C7 O1 C6 111.25(12) . .
C1 N1 C5 119.01(14) . .
C1 N1 Pd1 120.03(11) . .
C5 N1 Pd1 120.96(11) . .
N1 C1 C2 122.62(15) . .
N1 C1 H1 115.1(12) . .
C2 C1 H1 122.2(12) . .
C1 C2 C3 118.38(15) . .
C1 C2 C6 118.86(15) . .
C3 C2 C6 122.76(15) . .
C4 C3 C2 118.65(15) . .
C4 C3 H3 121.6(12) . .
C2 C3 H3 119.8(12) . .
C5 C4 C3 120.07(15) . .
C5 C4 H4 119.8(13) . .
C3 C4 H4 120.1(12) . .
N1 C5 C4 121.26(15) . .
N1 C5 H5 118.0(13) . .
C4 C5 H5 120.8(13) . .
O1 C6 C2 109.09(13) . .
O1 C6 H6A 108.5(12) . .
C2 C6 H6A 109.0(12) . .
O1 C6 H6B 109.7(12) . .
C2 C6 H6B 109.9(12) . .
H6A C6 H6B 110.5(17) . .
O1 C7 C8 107.17(13) . .
O1 C7 H7A 111.4(12) . .
C8 C7 H7A 108.1(12) . .
O1 C7 H7B 111.0(12) . .
C8 C7 H7B 107.1(12) . .
H7A C7 H7B 111.7(16) . .
F2 C8 F1 106.82(13) . .
F2 C8 C7 110.73(14) . .
F1 C8 C7 108.02(13) . .
F2 C8 C9 107.24(13) . .
F1 C8 C9 108.28(13) . .
C7 C8 C9 115.41(14) . .
F3 C9 F4 106.81(14) . .
F3 C9 C8 108.63(14) . .
F4 C9 C8 109.19(15) . .
F3 C9 H9 110.8(13) . .
F4 C9 H9 110.0(13) . .
C8 C9 H9 111.3(12) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Pd1 N1 2.0171(13) .
Pd1 N1 2.0171(13) 3_667
Pd1 Br1 2.43372(17) .
Pd1 Br1 2.43376(17) 3_667
F1 C8 1.3617(18) .
F2 C8 1.3612(19) .
F3 C9 1.354(2) .
F4 C9 1.358(2) .
O1 C7 1.4104(19) .
O1 C6 1.4217(19) .
N1 C1 1.340(2) .
N1 C5 1.348(2) .
C1 C2 1.384(2) .
C1 H1 0.96(2) .
C2 C3 1.391(2) .
C2 C6 1.501(2) .
C3 C4 1.384(2) .
C3 H3 0.95(2) .
C4 C5 1.375(2) .
C4 H4 0.94(2) .
C5 H5 0.91(2) .
C6 H6A 0.96(2) .
C6 H6B 0.97(2) .
C7 C8 1.502(2) .
C7 H7A 0.98(2) .
C7 H7B 0.95(2) .
C8 C9 1.520(2) .
C9 H9 0.96(2) .
