# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_lf6001b
_database_code_depnum_ccdc_archive 'CCDC 1432563'
_audit_update_record             
;
2015-10-21 deposited with the CCDC.
2017-08-08 downloaded from the CCDC.
;

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
trichloro[(S)-3-(2-(3,5-dimethyl-1H-pyrazol-1-yl)ethyl)-1-(1-phenylethyl)-1H-imidazol-3-ium-κ1N]palladium(II)
_chemical_formula_moiety         'C18 H23 Cl3 N4 Pd1'
_chemical_formula_sum            'C18 H23 Cl3 N4 Pd'
_chemical_formula_weight         508.15
_chemical_compound_source        'synthesis as described'
_chemical_absolute_configuration ad

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_Int_Tables_number      19
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'

_cell_length_a                   11.9601(3)
_cell_length_b                   12.4291(3)
_cell_length_c                   13.7982(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2051.15(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    180(2)
_cell_measurement_reflns_used    9957
_cell_measurement_theta_min      2.79
_cell_measurement_theta_max      30.02
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.02
_exptl_crystal_density_diffrn    1.646
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1024
_exptl_special_details           
;
 ?
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    1.305
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        [c.f. r.h. blessing, acta cryst. (1995), a51, 33-38]
;
_exptl_absorpt_correction_T_min  0.912
_exptl_absorpt_correction_T_max  0.995

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      180(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker Kappa APEX II'
_diffrn_measurement_method       ω-φ
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_av_R_equivalents  0.0302
_diffrn_reflns_av_unetI/netI     0.0301
_diffrn_reflns_number            31319
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.21
_diffrn_reflns_theta_max         30.1
_diffrn_reflns_theta_full        30.1
_diffrn_measured_fraction_theta_full 0.975
_diffrn_measured_fraction_theta_max 0.975
_reflns_number_total             5805
_reflns_number_gt                5187
_reflns_threshold_expression     >2σ(I)

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0239P)²+0.1954P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         5805
_refine_ls_number_parameters     238
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0308
_refine_ls_R_factor_gt           0.0239
_refine_ls_wR_factor_ref         0.0492
_refine_ls_wR_factor_gt          0.0467
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_restrained_S_all      1.016
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.029(19)
_refine_diff_density_max         0.887
_refine_diff_density_min         -0.303
_refine_diff_density_rms         0.066

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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_
_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
_atom_site_disorder_assembly
_atom_site_disorder_group
Pd1 Pd 0.750592(15) 0.770141(11) -0.029048(9) 0.01791(4) Uani 1 1 d . . .
Cl1 Cl 0.80057(5) 0.92463(5) 0.05335(4) 0.03303(13) Uani 1 1 d . . .
Cl2 Cl 0.75920(5) 0.85698(4) -0.17580(3) 0.02473(10) Uani 1 1 d . . .
Cl3 Cl 0.70266(5) 0.61369(4) -0.10763(4) 0.02835(11) Uani 1 1 d . . .
N3 N 0.52015(15) 0.85268(14) 0.22412(12) 0.0221(4) Uani 1 1 d . . .
N4 N 0.46682(15) 0.88103(16) 0.37119(13) 0.0240(4) Uani 1 1 d . . .
N1 N 0.74517(17) 0.69297(12) 0.10048(10) 0.0200(3) Uani 1 1 d . . .
N2 N 0.64814(15) 0.67190(16) 0.14993(13) 0.0192(4) Uani 1 1 d . . .
C3 C 0.54106(16) 0.70217(18) 0.10897(16) 0.0216(5) Uani 1 1 d . . .
H3A H 0.4812 0.66 0.1407 0.026 Uiso 1 1 calc R . .
H3B H 0.5404 0.6843 0.039 0.026 Uiso 1 1 calc R . .
C4 C 0.51699(18) 0.82097(18) 0.12153(15) 0.0230(4) Uani 1 1 d . . .
H14 H 0.573 0.8633 0.085 0.028 Uiso 1 1 calc R . .
H15 H 0.4423 0.8375 0.0945 0.028 Uiso 1 1 calc R . .
C5 C 0.61141(18) 0.89158(19) 0.27308(16) 0.0281(5) Uani 1 1 d . . .
H13 H 0.6839 0.9038 0.2471 0.034 Uiso 1 1 calc R . .
C6 C 0.57850(19) 0.9091(2) 0.36524(17) 0.0297(5) Uani 1 1 d . . .
H12 H 0.6236 0.9358 0.4165 0.036 Uiso 1 1 calc R . .
C7 C 0.39939(18) 0.88540(19) 0.46225(16) 0.0283(5) Uani 1 1 d . . .
H10 H 0.4197 0.9533 0.497 0.034 Uiso 1 1 calc R . .
C8 C 0.27571(18) 0.8917(2) 0.43696(18) 0.0379(6) Uani 1 1 d . . .
H4 H 0.2626 0.9535 0.3944 0.057 Uiso 1 1 calc R . .
H3 H 0.2319 0.9001 0.4965 0.057 Uiso 1 1 calc R . .
H2 H 0.253 0.8255 0.4037 0.057 Uiso 1 1 calc R . .
C9 C 0.43041(18) 0.79219(19) 0.52736(16) 0.0278(5) Uani 1 1 d . . .
C10 C 0.38004(19) 0.6921(2) 0.51911(19) 0.0360(6) Uani 1 1 d . . .
H9 H 0.3265 0.68 0.4695 0.043 Uiso 1 1 calc R . .
C11 C 0.4070(2) 0.6093(2) 0.5826(2) 0.0487(7) Uani 1 1 d . . .
H8 H 0.3716 0.5412 0.5766 0.058 Uiso 1 1 calc R . .
C12 C 0.4851(2) 0.6263(3) 0.6540(2) 0.0499(8) Uani 1 1 d . . .
H7 H 0.5025 0.5701 0.6982 0.06 Uiso 1 1 calc R . .
C13 C 0.5383(2) 0.7243(3) 0.6620(2) 0.0455(7) Uani 1 1 d . . .
H6 H 0.5933 0.7352 0.7107 0.055 Uiso 1 1 calc R . .
C14 C 0.51120(19) 0.8068(2) 0.59860(18) 0.0357(6) Uani 1 1 d . . .
H5 H 0.5483 0.8741 0.6039 0.043 Uiso 1 1 calc R . .
C15 C 0.43353(18) 0.84667(17) 0.28463(15) 0.0230(5) Uani 1 1 d . . .
H11 H 0.3606 0.8221 0.2687 0.028 Uiso 1 1 calc R . .
C16 C 0.67150(18) 0.62956(18) 0.23836(16) 0.0225(5) Uani 1 1 d . . .
C17 C 0.78542(17) 0.6210(2) 0.24458(16) 0.0244(5) Uani 1 1 d . . .
H16 H 0.8269 0.5931 0.2977 0.029 Uiso 1 1 calc R . .
C18 C 0.82917(18) 0.6614(2) 0.15705(18) 0.0246(5) Uani 1 1 d . . .
C19 C 0.94721(19) 0.6693(2) 0.12533(18) 0.0356(7) Uani 1 1 d . . .
H18 H 0.959 0.623 0.0687 0.053 Uiso 1 1 calc R . .
H17 H 0.9964 0.646 0.1781 0.053 Uiso 1 1 calc R . .
H19 H 0.9643 0.744 0.1082 0.053 Uiso 1 1 calc R . .
C20 C 0.58430(18) 0.6039(2) 0.31226(16) 0.0277(5) Uani 1 1 d . . .
H20 H 0.5708 0.6673 0.3529 0.042 Uiso 1 1 calc R . .
H22 H 0.61 0.5442 0.3529 0.042 Uiso 1 1 calc R . .
H21 H 0.5148 0.5834 0.2795 0.042 Uiso 1 1 calc R . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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 N1 2.0293(14) . ?
Pd1 Cl2 2.2969(5) . ?
Pd1 Cl3 2.2991(5) . ?
Pd1 Cl1 2.3102(6) . ?
N3 C15 1.333(3) . ?
N3 C5 1.372(3) . ?
N3 C4 1.470(3) . ?
N4 C15 1.329(3) . ?
N4 C6 1.383(3) . ?
N4 C7 1.494(3) . ?
N1 C18 1.331(3) . ?
N1 N2 1.372(2) . ?
N2 C16 1.358(3) . ?
N2 C3 1.450(3) . ?
C3 C4 1.514(3) . ?
C3 H3A 0.99 . ?
C3 H3B 0.99 . ?
C4 H14 0.99 . ?
C4 H15 0.99 . ?
C5 C6 1.349(3) . ?
C5 H13 0.95 . ?
C6 H12 0.95 . ?
C7 C9 1.512(3) . ?
C7 C8 1.522(3) . ?
C7 H10 1 . ?
C8 H4 0.98 . ?
C8 H3 0.98 . ?
C8 H2 0.98 . ?
C9 C10 1.387(3) . ?
C9 C14 1.390(3) . ?
C10 C11 1.389(4) . ?
C10 H9 0.95 . ?
C11 C12 1.374(4) . ?
C11 H8 0.95 . ?
C12 C13 1.379(4) . ?
C12 H7 0.95 . ?
C13 C14 1.387(4) . ?
C13 H6 0.95 . ?
C14 H5 0.95 . ?
C15 H11 0.95 . ?
C16 C17 1.369(3) . ?
C16 C20 1.493(3) . ?
C17 C18 1.409(3) . ?
C17 H16 0.95 . ?
C18 C19 1.481(3) . ?
C19 H18 0.98 . ?
C19 H17 0.98 . ?
C19 H19 0.98 . ?
C20 H20 0.98 . ?
C20 H22 0.98 . ?
C20 H21 0.98 . ?

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
N1 Pd1 Cl2 179.24(6) . . ?
N1 Pd1 Cl3 90.44(4) . . ?
Cl2 Pd1 Cl3 89.587(19) . . ?
N1 Pd1 Cl1 88.15(5) . . ?
Cl2 Pd1 Cl1 91.816(19) . . ?
Cl3 Pd1 Cl1 178.46(2) . . ?
C15 N3 C5 109.25(17) . . ?
C15 N3 C4 124.63(18) . . ?
C5 N3 C4 126.11(18) . . ?
C15 N4 C6 108.48(19) . . ?
C15 N4 C7 127.27(18) . . ?
C6 N4 C7 124.21(19) . . ?
C18 N1 N2 106.88(15) . . ?
C18 N1 Pd1 129.17(16) . . ?
N2 N1 Pd1 123.75(14) . . ?
C16 N2 N1 110.30(16) . . ?
C16 N2 C3 129.26(18) . . ?
N1 N2 C3 120.26(17) . . ?
N2 C3 C4 112.11(18) . . ?
N2 C3 H3A 109.2 . . ?
C4 C3 H3A 109.2 . . ?
N2 C3 H3B 109.2 . . ?
C4 C3 H3B 109.2 . . ?
H3A C3 H3B 107.9 . . ?
N3 C4 C3 111.52(18) . . ?
N3 C4 H14 109.3 . . ?
C3 C4 H14 109.3 . . ?
N3 C4 H15 109.3 . . ?
C3 C4 H15 109.3 . . ?
H14 C4 H15 108 . . ?
C6 C5 N3 106.80(19) . . ?
C6 C5 H13 126.6 . . ?
N3 C5 H13 126.6 . . ?
C5 C6 N4 107.3(2) . . ?
C5 C6 H12 126.4 . . ?
N4 C6 H12 126.4 . . ?
N4 C7 C9 109.84(18) . . ?
N4 C7 C8 109.49(19) . . ?
C9 C7 C8 114.5(2) . . ?
N4 C7 H10 107.6 . . ?
C9 C7 H10 107.6 . . ?
C8 C7 H10 107.6 . . ?
C7 C8 H4 109.5 . . ?
C7 C8 H3 109.5 . . ?
H4 C8 H3 109.5 . . ?
C7 C8 H2 109.5 . . ?
H4 C8 H2 109.5 . . ?
H3 C8 H2 109.5 . . ?
C10 C9 C14 118.5(2) . . ?
C10 C9 C7 122.1(2) . . ?
C14 C9 C7 119.4(2) . . ?
C9 C10 C11 120.8(2) . . ?
C9 C10 H9 119.6 . . ?
C11 C10 H9 119.6 . . ?
C12 C11 C10 119.7(3) . . ?
C12 C11 H8 120.1 . . ?
C10 C11 H8 120.1 . . ?
C11 C12 C13 120.5(3) . . ?
C11 C12 H7 119.8 . . ?
C13 C12 H7 119.8 . . ?
C12 C13 C14 119.7(3) . . ?
C12 C13 H6 120.2 . . ?
C14 C13 H6 120.2 . . ?
C13 C14 C9 120.8(2) . . ?
C13 C14 H5 119.6 . . ?
C9 C14 H5 119.6 . . ?
N4 C15 N3 108.18(19) . . ?
N4 C15 H11 125.9 . . ?
N3 C15 H11 125.9 . . ?
N2 C16 C17 106.9(2) . . ?
N2 C16 C20 123.56(18) . . ?
C17 C16 C20 129.5(2) . . ?
C16 C17 C18 106.7(2) . . ?
C16 C17 H16 126.6 . . ?
C18 C17 H16 126.6 . . ?
N1 C18 C17 109.12(19) . . ?
N1 C18 C19 121.8(2) . . ?
C17 C18 C19 129.1(2) . . ?
C18 C19 H18 109.5 . . ?
C18 C19 H17 109.5 . . ?
H18 C19 H17 109.5 . . ?
C18 C19 H19 109.5 . . ?
H18 C19 H19 109.5 . . ?
H17 C19 H19 109.5 . . ?
C16 C20 H20 109.5 . . ?
C16 C20 H22 109.5 . . ?
H20 C20 H22 109.5 . . ?
C16 C20 H21 109.5 . . ?
H20 C20 H21 109.5 . . ?
H22 C20 H21 109.5 . . ?

# The following lines are used to test the character set of files sent by
# network email or other means. They are not part of the CIF data set
# abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789
# !@#$%^&*()_+{}:"~<>?|\-=[];'`,./

# END of CIF
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: acetonitrile'
