# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
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#######################################################################

data_shelx
_database_code_depnum_ccdc_archive 'CCDC 1479722'
_audit_update_record             
;
2016-05-13 deposited with the CCDC.
2016-07-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H14 Cl N4 Pd, F6 P, C2 H3 N'
_chemical_formula_sum            'C16 H17 Cl F6 N5 P Pd'
_chemical_formula_weight         566.16

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'
F F 0.0171 0.0103 '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'
P P 0.1023 0.0942 '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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           62
_space_group_name_H-M_alt        'P n m a'
_space_group_name_Hall           '-P 2ac 2n'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z'
'x+1/2, -y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z'
'-x-1/2, y-1/2, z-1/2'

_cell_length_a                   26.847(3)
_cell_length_b                   6.6403(7)
_cell_length_c                   11.0216(11)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1964.8(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    3690
_cell_measurement_theta_min      2.93
_cell_measurement_theta_max      28.38

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.914
_exptl_crystal_F_000             1120
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.1
_exptl_absorpt_coefficient_mu    1.232
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.65
_exptl_absorpt_correction_T_max  0.746
_exptl_absorpt_process_details   
;
SADABS, Bruker AXS Inc., Madison, 
Wisconsin, USA. 
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15429
_diffrn_reflns_av_unetI/netI     0.0457
_diffrn_reflns_av_R_equivalents  0.0565
_diffrn_reflns_limit_h_min       -37
_diffrn_reflns_limit_h_max       35
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.997
_diffrn_reflns_theta_max         30.018
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3091
_reflns_number_gt                2442
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
We suspect a symetry issue in this compound and its Pt analoguous.
A few signs alerted us and we tried a series of refinement using 
Twin commands, changing space group even to monoclinic system. 
We decided to remain in Pnma symetry as we were not able to 
exclude it definitively. 

 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'DIAMOND (Brandenburg, 2006)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0025P)²+16.4799P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3091
_refine_ls_number_parameters     179
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0964
_refine_ls_R_factor_gt           0.0747
_refine_ls_wR_factor_ref         0.1438
_refine_ls_wR_factor_gt          0.1381
_refine_ls_goodness_of_fit_ref   1.390
_refine_ls_restrained_S_all      1.390
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
_atom_site_disorder_assembly
_atom_site_disorder_group
Pd1 Pd 0.99032(2) 0.2500 0.99382(6) 0.01802(15) Uani 1 2 d S T P . .
Cl1 Cl 0.98215(9) 0.2500 1.20790(17) 0.0258(5) Uani 1 2 d S T P . .
N1 N 0.9174(3) 0.2500 0.9470(6) 0.0185(14) Uani 1 2 d S T P . .
N2 N 0.9542(3) 0.2500 0.7575(6) 0.0207(15) Uani 1 2 d S T P . .
N3 N 1.0415(3) 0.2500 0.7754(6) 0.0183(14) Uani 1 2 d S T P . .
N4 N 1.0654(3) 0.2500 0.9762(6) 0.0210(15) Uani 1 2 d S T P . .
C1 C 0.9973(3) 0.2500 0.8232(7) 0.0175(16) Uani 1 2 d S T P . .
C2 C 1.0496(3) 0.2500 0.6415(8) 0.027(2) Uani 1 2 d S T P . .
H2A H 1.0786 0.1642 0.6210 0.032 Uiso 0.5 1 calc R U P . .
H2B H 1.0566 0.3886 0.6131 0.032 Uiso 0.5 1 calc R U P . .
C3 C 1.0034(5) 0.1701(19) 0.5796(9) 0.030(3) Uani 0.5 1 d . . P . .
H3A H 1.0061 0.1990 0.4917 0.036 Uiso 0.5 1 calc R U P . .
H3B H 1.0029 0.0218 0.5891 0.036 Uiso 0.5 1 calc R U P . .
C4 C 0.9551(4) 0.2500 0.6229(7) 0.034(2) Uani 1 2 d S T P . .
H4A H 0.9276 0.1656 0.5915 0.041 Uiso 0.5 1 calc R U P . .
H4B H 0.9504 0.3889 0.5924 0.041 Uiso 0.5 1 calc R U P . .
C5 C 0.9099(3) 0.2500 0.8239(7) 0.0213(17) Uani 1 2 d S T P . .
C6 C 0.8627(4) 0.2500 0.7736(8) 0.031(2) Uani 1 2 d S T P . .
H6 H 0.8582 0.2500 0.6881 0.037 Uiso 1 2 calc R U P . .
C7 C 0.8224(4) 0.2500 0.8514(9) 0.034(2) Uani 1 2 d S T P . .
H7 H 0.7895 0.2500 0.8197 0.041 Uiso 1 2 calc R U P . .
C8 C 0.8299(4) 0.2500 0.9745(9) 0.033(2) Uani 1 2 d S T P . .
H8 H 0.8022 0.2500 1.0282 0.039 Uiso 1 2 calc R U P . .
C9 C 0.8777(3) 0.2500 1.0202(8) 0.0270(19) Uani 1 2 d S T P . .
H9 H 0.8825 0.2500 1.1055 0.032 Uiso 1 2 calc R U P . .
C10 C 1.0805(3) 0.2500 0.8599(7) 0.0204(17) Uani 1 2 d S T P . .
C11 C 1.1302(3) 0.2500 0.8268(9) 0.030(2) Uani 1 2 d S T P . .
H11 H 1.1401 0.2500 0.7441 0.035 Uiso 1 2 calc R U P . .
C12 C 1.1646(4) 0.2500 0.9195(10) 0.042(3) Uani 1 2 d S T P . .
H12 H 1.1991 0.2500 0.9005 0.050 Uiso 1 2 calc R U P . .
C13 C 1.1499(4) 0.2500 1.0385(9) 0.034(2) Uani 1 2 d S T P . .
H13 H 1.1738 0.2500 1.1020 0.041 Uiso 1 2 calc R U P . .
C14 C 1.0999(3) 0.2500 1.0640(8) 0.0230(18) Uani 1 2 d S T P . .
H14 H 1.0894 0.2500 1.1463 0.028 Uiso 1 2 calc R U P . .
P1 P 0.69254(10) 0.7500 0.8942(2) 0.0352(6) Uani 1 2 d S T P . .
F1 F 0.6805(3) 0.7500 0.7558(6) 0.091(3) Uani 1 2 d S T P . .
F2 F 0.65250(19) 0.9199(10) 0.9185(5) 0.0747(17) Uani 1 1 d . . . . .
F3 F 0.7338(2) 0.9175(9) 0.8734(5) 0.0692(16) Uani 1 1 d . . . . .
F4 F 0.7061(3) 0.7500 1.0347(6) 0.069(2) Uani 1 2 d S T P . .
N5 N 0.6033(4) 0.2500 0.1255(8) 0.061(3) Uani 1 2 d S T P . .
C15 C 0.6453(4) 0.2500 0.1201(9) 0.044(3) Uani 1 2 d S T P . .
C16 C 0.6992(4) 0.2500 0.1125(12) 0.054(3) Uani 1 2 d S T P . .
H16B H 0.7129 0.1668 0.1779 0.080 Uiso 0.5 1 calc R U P A -1
H16A H 0.7115 0.3882 0.1206 0.080 Uiso 0.5 1 calc R U P A -1
H16C H 0.7095 0.1950 0.0340 0.080 Uiso 0.5 1 calc R U P A -1


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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
Pd1 C1 1.890(8) . ?
Pd1 N4 2.026(7) . ?
Pd1 N1 2.026(7) . ?
Pd1 Cl1 2.370(2) . ?
N1 C9 1.336(10) . ?
N1 C5 1.370(10) . ?
N2 C1 1.365(10) . ?
N2 C5 1.397(11) . ?
N2 C4 1.483(10) . ?
N3 C1 1.300(10) . ?
N3 C10 1.400(11) . ?
N3 C2 1.492(10) . ?
N4 C14 1.338(10) . ?
N4 C10 1.344(10) . ?
C2 C3 1.513(15) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.479(15) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.383(12) . ?
C6 C7 1.381(13) . ?
C6 H6 0.9500 . ?
C7 C8 1.372(13) . ?
C7 H7 0.9500 . ?
C8 C9 1.378(13) . ?
C8 H8 0.9500 . ?
C9 H9 0.9500 . ?
C10 C11 1.384(12) . ?
C11 C12 1.377(14) . ?
C11 H11 0.9500 . ?
C12 C13 1.369(15) . ?
C12 H12 0.9500 . ?
C13 C14 1.372(13) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
P1 F1 1.559(7) . ?
P1 F2 1.581(5) . ?
P1 F2 1.582(5) 7_575 ?
P1 F3 1.586(5) 7_575 ?
P1 F3 1.586(5) . ?
P1 F4 1.591(7) . ?
N5 C15 1.130(14) . ?
C15 C16 1.448(15) . ?
C16 H16B 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16C 0.9800 . ?

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
C1 Pd1 N4 78.8(3) . . ?
C1 Pd1 N1 80.9(3) . . ?
N4 Pd1 N1 159.7(3) . . ?
C1 Pd1 Cl1 179.6(2) . . ?
N4 Pd1 Cl1 100.8(2) . . ?
N1 Pd1 Cl1 99.5(2) . . ?
C9 N1 C5 118.8(7) . . ?
C9 N1 Pd1 128.1(6) . . ?
C5 N1 Pd1 113.2(5) . . ?
C1 N2 C5 116.3(7) . . ?
C1 N2 C4 121.1(7) . . ?
C5 N2 C4 122.6(7) . . ?
C1 N3 C10 114.4(7) . . ?
C1 N3 C2 122.2(7) . . ?
C10 N3 C2 123.4(7) . . ?
C14 N4 C10 118.8(7) . . ?
C14 N4 Pd1 128.2(6) . . ?
C10 N4 Pd1 113.0(6) . . ?
N3 C1 N2 124.0(7) . . ?
N3 C1 Pd1 119.6(6) . . ?
N2 C1 Pd1 116.4(6) . . ?
N3 C2 C3 109.1(7) . . ?
N3 C2 H2A 109.9 . . ?
C3 C2 H2A 109.9 . . ?
N3 C2 H2B 109.9 . . ?
C3 C2 H2B 109.9 . . ?
H2A C2 H2B 108.3 . . ?
C4 C3 C2 116.6(9) . . ?
C4 C3 H3A 108.2 . . ?
C2 C3 H3A 108.2 . . ?
C4 C3 H3B 108.2 . . ?
C2 C3 H3B 108.2 . . ?
H3A C3 H3B 107.3 . . ?
C3 C4 N2 109.7(7) . . ?
C3 C4 H4A 109.7 . . ?
N2 C4 H4A 109.7 . . ?
C3 C4 H4B 109.7 . . ?
N2 C4 H4B 109.7 . . ?
H4A C4 H4B 108.2 . . ?
N1 C5 C6 122.1(8) . . ?
N1 C5 N2 113.2(7) . . ?
C6 C5 N2 124.7(8) . . ?
C7 C6 C5 117.9(8) . . ?
C7 C6 H6 121.0 . . ?
C5 C6 H6 121.0 . . ?
C8 C7 C6 120.0(9) . . ?
C8 C7 H7 120.0 . . ?
C6 C7 H7 120.0 . . ?
C7 C8 C9 119.8(9) . . ?
C7 C8 H8 120.1 . . ?
C9 C8 H8 120.1 . . ?
N1 C9 C8 121.5(8) . . ?
N1 C9 H9 119.3 . . ?
C8 C9 H9 119.3 . . ?
N4 C10 C11 122.8(8) . . ?
N4 C10 N3 114.2(7) . . ?
C11 C10 N3 123.0(8) . . ?
C12 C11 C10 116.8(9) . . ?
C12 C11 H11 121.6 . . ?
C10 C11 H11 121.6 . . ?
C13 C12 C11 121.2(9) . . ?
C13 C12 H12 119.4 . . ?
C11 C12 H12 119.4 . . ?
C12 C13 C14 118.5(9) . . ?
C12 C13 H13 120.7 . . ?
C14 C13 H13 120.7 . . ?
N4 C14 C13 121.9(8) . . ?
N4 C14 H14 119.0 . . ?
C13 C14 H14 119.0 . . ?
F1 P1 F2 91.4(3) . . ?
F1 P1 F2 91.4(3) . 7_575 ?
F2 P1 F2 91.0(5) . 7_575 ?
F1 P1 F3 90.2(3) . 7_575 ?
F2 P1 F3 178.1(4) . 7_575 ?
F2 P1 F3 89.9(3) 7_575 7_575 ?
F1 P1 F3 90.2(3) . . ?
F2 P1 F3 89.9(3) . . ?
F2 P1 F3 178.1(4) 7_575 . ?
F3 P1 F3 89.1(5) 7_575 . ?
F1 P1 F4 178.7(5) . . ?
F2 P1 F4 89.5(3) . . ?
F2 P1 F4 89.5(3) 7_575 . ?
F3 P1 F4 88.9(3) 7_575 . ?
F3 P1 F4 88.9(3) . . ?
N5 C15 C16 179.7(11) . . ?
C15 C16 H16B 109.5 . . ?
C15 C16 H16A 109.5 . . ?
H16B C16 H16A 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?

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
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C10 N3 C1 N2 180.000(1) . . . . ?
C2 N3 C1 N2 0.000(2) . . . . ?
C10 N3 C1 Pd1 0.000(1) . . . . ?
C2 N3 C1 Pd1 180.000(1) . . . . ?
C5 N2 C1 N3 180.000(1) . . . . ?
C4 N2 C1 N3 0.000(2) . . . . ?
C5 N2 C1 Pd1 0.000(1) . . . . ?
C4 N2 C1 Pd1 180.000(1) . . . . ?
N4 Pd1 C1 N3 0.000(1) . . . . ?
N1 Pd1 C1 N3 180.000(1) . . . . ?
N4 Pd1 C1 N2 180.000(1) . . . . ?
N1 Pd1 C1 N2 0.000(1) . . . . ?
C1 N3 C2 C3 -21.8(5) . . . . ?
C10 N3 C2 C3 158.2(5) . . . . ?
N3 C2 C3 C4 45.5(9) . . . . ?
C2 C3 C4 N2 -45.7(9) . . . . ?
C1 N2 C4 C3 22.4(6) . . . . ?
C5 N2 C4 C3 -157.6(6) . . . . ?
C9 N1 C5 C6 0.000(2) . . . . ?
Pd1 N1 C5 C6 180.000(2) . . . . ?
C9 N1 C5 N2 180.000(1) . . . . ?
Pd1 N1 C5 N2 0.000(2) . . . . ?
C1 N2 C5 N1 0.000(2) . . . . ?
C4 N2 C5 N1 180.000(1) . . . . ?
C1 N2 C5 C6 180.000(2) . . . . ?
C4 N2 C5 C6 0.000(2) . . . . ?
N1 C5 C6 C7 0.000(2) . . . . ?
N2 C5 C6 C7 180.000(2) . . . . ?
C5 C6 C7 C8 0.000(2) . . . . ?
C6 C7 C8 C9 0.000(2) . . . . ?
C5 N1 C9 C8 0.000(3) . . . . ?
Pd1 N1 C9 C8 180.000(2) . . . . ?
C7 C8 C9 N1 0.000(3) . . . . ?
C14 N4 C10 C11 0.000(2) . . . . ?
Pd1 N4 C10 C11 180.000(2) . . . . ?
C14 N4 C10 N3 180.000(2) . . . . ?
Pd1 N4 C10 N3 0.000(2) . . . . ?
C1 N3 C10 N4 0.000(2) . . . . ?
C2 N3 C10 N4 180.000(1) . . . . ?
C1 N3 C10 C11 180.000(2) . . . . ?
C2 N3 C10 C11 0.000(2) . . . . ?
N4 C10 C11 C12 0.000(3) . . . . ?
N3 C10 C11 C12 180.000(2) . . . . ?
C10 C11 C12 C13 0.000(3) . . . . ?
C11 C12 C13 C14 0.000(3) . . . . ?
C10 N4 C14 C13 0.000(3) . . . . ?
Pd1 N4 C14 C13 180.000(2) . . . . ?
C12 C13 C14 N4 0.000(3) . . . . ?

_refine_diff_density_max         1.178
_refine_diff_density_min         -1.881
_refine_diff_density_rms         0.160

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_shelx
_database_code_depnum_ccdc_archive 'CCDC 1479723'
_audit_update_record             
;
2016-05-13 deposited with the CCDC.
2016-07-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H14 Cl N4 Pt, F6 P, C2 H3 N'
_chemical_formula_sum            'C16 H17 Cl F6 N5 P Pt'
_chemical_formula_weight         654.85

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'
F F 0.0171 0.0103 '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'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Pt Pt -1.7033 8.3905 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           62
_space_group_name_H-M_alt        'P n m a'
_space_group_name_Hall           '-P 2ac 2n'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z'
'x+1/2, -y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z'
'-x-1/2, y-1/2, z-1/2'

_cell_length_a                   26.8248(13)
_cell_length_b                   6.6453(3)
_cell_length_c                   11.0181(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1964.07(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    4604
_cell_measurement_theta_min      3.04
_cell_measurement_theta_max      29.99

_exptl_crystal_description       block
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    2.215
_exptl_crystal_F_000             1248
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.07
_exptl_absorpt_coefficient_mu    7.431
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.57
_exptl_absorpt_correction_T_max  0.746
_exptl_absorpt_process_details   
;
SADABS, Bruker AXS Inc., Madison, 
Wisconsin, USA. 
;

_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15613
_diffrn_reflns_av_unetI/netI     0.0319
_diffrn_reflns_av_R_equivalents  0.0376
_diffrn_reflns_limit_h_min       -37
_diffrn_reflns_limit_h_max       36
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.392
_diffrn_reflns_theta_max         30.111
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             3108
_reflns_number_gt                2627
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
We suspect a symetry issue in this compound and its Pd analoguous.
A few signs alerted us and we tried a series of refinement using 
Twin commands, changing space group even to monoclinic system. 
We decided to remain in Pnma symetry as we were not able to 
exclude it definitively. 

 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'bruker SAINT'
_computing_data_reduction        'bruker SAINT'
_computing_structure_solution    'SUPERFLIP (Palatinus & Chapuis,2007)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'DIAMOND (Brandenburg, 2006)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0096P)²+40.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3108
_refine_ls_number_parameters     179
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0575
_refine_ls_R_factor_gt           0.0454
_refine_ls_wR_factor_ref         0.0951
_refine_ls_wR_factor_gt          0.0910
_refine_ls_goodness_of_fit_ref   1.005
_refine_ls_restrained_S_all      1.005
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

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
_atom_site_disorder_assembly
_atom_site_disorder_group
Pt1 Pt 0.99081(2) 0.2500 0.99388(3) 0.01814(9) Uani 1 2 d S T P . .
Cl1 Cl 0.98234(10) 0.2500 1.20805(19) 0.0270(5) Uani 1 2 d S T P . .
N1 N 0.9181(3) 0.2500 0.9477(6) 0.0191(14) Uani 1 2 d S T P B .
N2 N 0.9546(3) 0.2500 0.7573(7) 0.0212(15) Uani 1 2 d S T P B .
N3 N 1.0423(3) 0.2500 0.7761(7) 0.0187(14) Uani 1 2 d S T P B .
N4 N 1.0659(3) 0.2500 0.9773(7) 0.0215(15) Uani 1 2 d S T P B .
C1 C 0.9979(3) 0.2500 0.8233(8) 0.0194(17) Uani 1 2 d S T P . .
C2 C 1.0496(4) 0.2500 0.6425(8) 0.031(2) Uani 1 2 d S T P . .
H2A H 1.0783 0.1629 0.6216 0.037 Uiso 0.5 1 calc R U P A 1
H2B H 1.0573 0.3883 0.6148 0.037 Uiso 0.5 1 calc R U P A 1
C3 C 1.0041(5) 0.176(2) 0.5790(11) 0.033(3) Uani 0.5 1 d . . P B 1
H3A H 1.0071 0.2112 0.4920 0.039 Uiso 0.5 1 calc R U P B 1
H3B H 1.0038 0.0269 0.5843 0.039 Uiso 0.5 1 calc R U P B 1
C4 C 0.9553(4) 0.2500 0.6227(8) 0.031(2) Uani 1 2 d S T P . .
H4A H 0.9283 0.1625 0.5915 0.037 Uiso 0.5 1 calc R U P B 1
H4B H 0.9496 0.3882 0.5922 0.037 Uiso 0.5 1 calc R U P B 1
C5 C 0.9106(3) 0.2500 0.8249(8) 0.0225(18) Uani 1 2 d S T P . .
C6 C 0.8632(4) 0.2500 0.7753(10) 0.036(2) Uani 1 2 d S T P B .
H6 H 0.8587 0.2500 0.6898 0.044 Uiso 1 2 calc R U P . .
C7 C 0.8226(4) 0.2500 0.8526(10) 0.035(2) Uani 1 2 d S T P . .
H7 H 0.7897 0.2500 0.8207 0.042 Uiso 1 2 calc R U P B .
C8 C 0.8303(4) 0.2500 0.9757(10) 0.037(2) Uani 1 2 d S T P B .
H8 H 0.8026 0.2500 1.0293 0.045 Uiso 1 2 calc R U P . .
C9 C 0.8780(4) 0.2500 1.0218(9) 0.030(2) Uani 1 2 d S T P . .
H9 H 0.8828 0.2500 1.1072 0.036 Uiso 1 2 calc R U P B .
C10 C 1.0809(3) 0.2500 0.8604(8) 0.0199(17) Uani 1 2 d S T P . .
C11 C 1.1308(4) 0.2500 0.8285(10) 0.033(2) Uani 1 2 d S T P B .
H11 H 1.1408 0.2500 0.7457 0.040 Uiso 1 2 calc R U P . .
C12 C 1.1657(4) 0.2500 0.9207(11) 0.042(3) Uani 1 2 d S T P . .
H12 H 1.2003 0.2500 0.9020 0.051 Uiso 1 2 calc R U P B .
C13 C 1.1501(4) 0.2500 1.0403(10) 0.033(2) Uani 1 2 d S T P B .
H13 H 1.1739 0.2500 1.1042 0.040 Uiso 1 2 calc R U P . .
C14 C 1.0995(4) 0.2500 1.0660(8) 0.0239(19) Uani 1 2 d S T P . .
H14 H 1.0887 0.2500 1.1481 0.029 Uiso 1 2 calc R U P B .
P1 P 0.69197(11) 0.7500 0.8940(3) 0.0375(7) Uani 1 2 d S T P . .
F1 F 0.6803(4) 0.7500 0.7556(8) 0.102(4) Uani 1 2 d S T P . .
F2 F 0.6520(2) 0.9186(12) 0.9179(7) 0.083(2) Uani 1 1 d . . . . .
F3 F 0.7333(2) 0.9167(11) 0.8735(6) 0.0745(19) Uani 1 1 d . . . . .
F4 F 0.7052(3) 0.7500 1.0345(7) 0.075(3) Uani 1 2 d S T P . .
N5 N 0.6038(5) 0.2500 0.1248(10) 0.072(4) Uani 1 2 d S T P . .
C15 C 0.6458(5) 0.2500 0.1191(10) 0.050(3) Uani 1 2 d S T P . .
C16 C 0.6993(5) 0.2500 0.1112(14) 0.059(4) Uani 1 2 d S T P . .
H16A H 0.7131 0.1650 0.1757 0.088 Uiso 0.5 1 calc R U P C -1
H16B H 0.7118 0.3878 0.1207 0.088 Uiso 0.5 1 calc R U P C -1
H16C H 0.7096 0.1973 0.0320 0.088 Uiso 0.5 1 calc R U P C -1


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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
Pt1 C1 1.889(9) . ?
Pt1 N1 2.015(8) . ?
Pt1 N4 2.023(8) . ?
Pt1 Cl1 2.371(2) . ?
N1 C9 1.351(12) . ?
N1 C5 1.367(11) . ?
N2 C1 1.369(11) . ?
N2 C5 1.395(11) . ?
N2 C4 1.483(11) . ?
N3 C1 1.300(11) . ?
N3 C10 1.390(11) . ?
N3 C2 1.485(11) . ?
N4 C14 1.329(11) . ?
N4 C10 1.348(11) . ?
C2 C3 1.492(17) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.479(17) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.385(14) . ?
C6 C7 1.382(16) . ?
C6 H6 0.9500 . ?
C7 C8 1.372(15) . ?
C7 H7 0.9500 . ?
C8 C9 1.376(15) . ?
C8 H8 0.9500 . ?
C9 H9 0.9500 . ?
C10 C11 1.385(14) . ?
C11 C12 1.382(15) . ?
C11 H11 0.9500 . ?
C12 C13 1.382(16) . ?
C12 H12 0.9500 . ?
C13 C14 1.387(15) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
P1 F1 1.557(9) . ?
P1 F2 1.574(6) . ?
P1 F2 1.574(7) 7_575 ?
P1 F3 1.583(6) 7_575 ?
P1 F3 1.583(6) . ?
P1 F4 1.588(8) . ?
N5 C15 1.128(17) . ?
C15 C16 1.439(19) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?

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
C1 Pt1 N1 81.1(3) . . ?
C1 Pt1 N4 79.0(3) . . ?
N1 Pt1 N4 160.2(3) . . ?
C1 Pt1 Cl1 179.7(3) . . ?
N1 Pt1 Cl1 99.1(2) . . ?
N4 Pt1 Cl1 100.7(2) . . ?
C9 N1 C5 118.7(8) . . ?
C9 N1 Pt1 128.2(6) . . ?
C5 N1 Pt1 113.1(6) . . ?
C1 N2 C5 115.7(7) . . ?
C1 N2 C4 121.3(8) . . ?
C5 N2 C4 123.0(8) . . ?
C1 N3 C10 114.5(7) . . ?
C1 N3 C2 121.1(8) . . ?
C10 N3 C2 124.4(8) . . ?
C14 N4 C10 120.0(8) . . ?
C14 N4 Pt1 127.5(6) . . ?
C10 N4 Pt1 112.5(6) . . ?
N3 C1 N2 124.4(8) . . ?
N3 C1 Pt1 119.3(6) . . ?
N2 C1 Pt1 116.3(6) . . ?
N3 C2 C3 111.0(8) . . ?
N3 C2 H2A 109.4 . . ?
C3 C2 H2A 109.4 . . ?
N3 C2 H2B 109.4 . . ?
C3 C2 H2B 109.4 . . ?
H2A C2 H2B 108.0 . . ?
C4 C3 C2 117.4(10) . . ?
C4 C3 H3A 108.0 . . ?
C2 C3 H3A 108.0 . . ?
C4 C3 H3B 108.0 . . ?
C2 C3 H3B 108.0 . . ?
H3A C3 H3B 107.2 . . ?
C3 C4 N2 109.7(8) . . ?
C3 C4 H4A 109.7 . . ?
N2 C4 H4A 109.7 . . ?
C3 C4 H4B 109.7 . . ?
N2 C4 H4B 109.7 . . ?
H4A C4 H4B 108.2 . . ?
N1 C5 C6 121.7(9) . . ?
N1 C5 N2 113.8(8) . . ?
C6 C5 N2 124.5(9) . . ?
C5 C6 C7 118.7(10) . . ?
C5 C6 H6 120.6 . . ?
C7 C6 H6 120.6 . . ?
C8 C7 C6 119.4(10) . . ?
C8 C7 H7 120.3 . . ?
C6 C7 H7 120.3 . . ?
C7 C8 C9 120.3(10) . . ?
C7 C8 H8 119.9 . . ?
C9 C8 H8 119.9 . . ?
N1 C9 C8 121.2(9) . . ?
N1 C9 H9 119.4 . . ?
C8 C9 H9 119.4 . . ?
N4 C10 C11 122.0(9) . . ?
N4 C10 N3 114.6(8) . . ?
C11 C10 N3 123.3(9) . . ?
C12 C11 C10 117.9(10) . . ?
C12 C11 H11 121.0 . . ?
C10 C11 H11 121.0 . . ?
C11 C12 C13 119.7(10) . . ?
C11 C12 H12 120.1 . . ?
C13 C12 H12 120.1 . . ?
C14 C13 C12 119.4(10) . . ?
C14 C13 H13 120.3 . . ?
C12 C13 H13 120.3 . . ?
N4 C14 C13 120.9(9) . . ?
N4 C14 H14 119.6 . . ?
C13 C14 H14 119.6 . . ?
F1 P1 F2 91.5(4) . . ?
F1 P1 F2 91.5(4) . 7_575 ?
F2 P1 F2 90.8(6) . 7_575 ?
F1 P1 F3 90.1(4) . 7_575 ?
F2 P1 F3 178.1(4) . 7_575 ?
F2 P1 F3 90.2(4) 7_575 7_575 ?
F1 P1 F3 90.1(4) . . ?
F2 P1 F3 90.2(4) . . ?
F2 P1 F3 178.1(4) 7_575 . ?
F3 P1 F3 88.8(5) 7_575 . ?
F1 P1 F4 178.8(6) . . ?
F2 P1 F4 89.4(4) . . ?
F2 P1 F4 89.4(4) 7_575 . ?
F3 P1 F4 89.0(4) 7_575 . ?
F3 P1 F4 89.0(4) . . ?
N5 C15 C16 179.7(13) . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?

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
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C10 N3 C1 N2 180.000(2) . . . . ?
C2 N3 C1 N2 0.000(2) . . . . ?
C10 N3 C1 Pt1 0.000(1) . . . . ?
C2 N3 C1 Pt1 180.000(1) . . . . ?
C5 N2 C1 N3 180.000(2) . . . . ?
C4 N2 C1 N3 0.000(2) . . . . ?
C5 N2 C1 Pt1 0.000(1) . . . . ?
C4 N2 C1 Pt1 180.000(1) . . . . ?
N1 Pt1 C1 N3 180.000(1) . . . . ?
N4 Pt1 C1 N3 0.000(1) . . . . ?
N1 Pt1 C1 N2 0.000(1) . . . . ?
N4 Pt1 C1 N2 180.000(1) . . . . ?
C1 N3 C2 C3 -20.8(6) . . . . ?
C10 N3 C2 C3 159.2(6) . . . . ?
N3 C2 C3 C4 43.2(11) . . . . ?
C2 C3 C4 N2 -42.7(11) . . . . ?
C1 N2 C4 C3 20.8(6) . . . . ?
C5 N2 C4 C3 -159.2(6) . . . . ?
C9 N1 C5 C6 0.000(2) . . . . ?
Pt1 N1 C5 C6 180.000(2) . . . . ?
C9 N1 C5 N2 180.000(2) . . . . ?
Pt1 N1 C5 N2 0.000(2) . . . . ?
C1 N2 C5 N1 0.000(2) . . . . ?
C4 N2 C5 N1 180.000(1) . . . . ?
C1 N2 C5 C6 180.000(2) . . . . ?
C4 N2 C5 C6 0.000(2) . . . . ?
N1 C5 C6 C7 0.000(3) . . . . ?
N2 C5 C6 C7 180.000(2) . . . . ?
C5 C6 C7 C8 0.000(3) . . . . ?
C6 C7 C8 C9 0.000(3) . . . . ?
C5 N1 C9 C8 0.000(3) . . . . ?
Pt1 N1 C9 C8 180.000(2) . . . . ?
C7 C8 C9 N1 0.000(3) . . . . ?
C14 N4 C10 C11 0.000(3) . . . . ?
Pt1 N4 C10 C11 180.000(2) . . . . ?
C14 N4 C10 N3 180.000(2) . . . . ?
Pt1 N4 C10 N3 0.000(2) . . . . ?
C1 N3 C10 N4 0.000(2) . . . . ?
C2 N3 C10 N4 180.000(2) . . . . ?
C1 N3 C10 C11 180.000(2) . . . . ?
C2 N3 C10 C11 0.000(2) . . . . ?
N4 C10 C11 C12 0.000(3) . . . . ?
N3 C10 C11 C12 180.000(2) . . . . ?
C10 C11 C12 C13 0.000(3) . . . . ?
C11 C12 C13 C14 0.000(3) . . . . ?
C10 N4 C14 C13 0.000(3) . . . . ?
Pt1 N4 C14 C13 180.000(2) . . . . ?
C12 C13 C14 N4 0.000(3) . . . . ?

_refine_diff_density_max         2.916
_refine_diff_density_min         -1.881
_refine_diff_density_rms         0.165

_shelxl_version_number           2013-4

