# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_smm803
_database_code_depnum_ccdc_archive 'CCDC 1573135'
_audit_update_record             
;
2017-09-07 deposited with the CCDC.
2018-08-30 downloaded from the CCDC.
;
_audit_creation_date             2017-08-04
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H18 I2 N4 Pd'
_chemical_formula_sum            'C16 H18 I2 N4 Pd'
_chemical_formula_weight         626.54
_chemical_melting_point          ?
_chemical_oxdiff_formula         C16H18I2N4Pd
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'
I I -0.4742 1.8119 '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'
Pd Pd -0.9988 1.0072 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
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'

_cell_length_a                   10.7786(5)
_cell_length_b                   8.1520(3)
_cell_length_c                   23.4486(10)
_cell_angle_alpha                90
_cell_angle_beta                 99.338(4)
_cell_angle_gamma                90
_cell_volume                     2033.06(15)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5671
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.7110
_cell_measurement_theta_min      3.7190
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    3.953
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.33408
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear yellowish yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    2.047
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       cube
_exptl_crystal_F_000             1176
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0283
_diffrn_reflns_av_unetI/netI     0.0267
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.877
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            11043
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.877
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.841
_diffrn_reflns_theta_min         3.000
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0309
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.877
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   42.00   86.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       17.1097   37.0000 -180.0000 44

#__ type_ start__ end____ width___ exp.time_
  2 omega   -7.00   18.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       17.1097   37.0000 -180.0000 25

#__ type_ start__ end____ width___ exp.time_
  3 omega   43.00   86.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       17.1097  178.0000   60.0000 43

#__ type_ start__ end____ width___ exp.time_
  4 omega    0.00   59.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       17.1097  -99.0000 -150.0000 59

#__ type_ start__ end____ width___ exp.time_
  5 omega   65.00   92.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       17.1097  178.0000 -180.0000 27

#__ type_ start__ end____ width___ exp.time_
  6 omega  -44.00    1.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       17.1097  -37.0000   60.0000 45

#__ type_ start__ end____ width___ exp.time_
  7 omega    7.00   39.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       17.1097  -37.0000   60.0000 32

#__ type_ start__ end____ width___ exp.time_
  8 omega  -62.00  -34.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      -18.9847  142.0000 -176.0000 28
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0283517000
_diffrn_orient_matrix_UB_12      0.0273814000
_diffrn_orient_matrix_UB_13      0.0278682000
_diffrn_orient_matrix_UB_21      0.0413952000
_diffrn_orient_matrix_UB_22      0.0510420000
_diffrn_orient_matrix_UB_23      -0.0127927000
_diffrn_orient_matrix_UB_31      -0.0442624000
_diffrn_orient_matrix_UB_32      0.0652326000
_diffrn_orient_matrix_UB_33      -0.0016348000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4080
_reflns_number_total             4670
_reflns_odcompleteness_completeness 99.73
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         1.805
_refine_diff_density_min         -1.335
_refine_diff_density_rms         0.123
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     211
_refine_ls_number_reflns         4670
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0488
_refine_ls_R_factor_gt           0.0434
_refine_ls_restrained_S_all      1.045
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0550P)²+4.2700P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1117
_refine_ls_wR_factor_ref         0.1154
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C6(H6), C7(H7), C3(H3), C13(H13), C12(H12), C14(H14), C16(H16),
 C15(H15)
2.b Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C10(H10A,H10B,H10C), C1(H1A,H1B,H1C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
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 0.33885(3) 0.15271(5) 0.13642(2) 0.04133(12) Uani 1 1 d . . . . .
I2 I 0.52149(4) -0.05141(5) 0.16834(2) 0.06227(14) Uani 1 1 d . . . . .
I1 I 0.15115(4) 0.35623(5) 0.11050(2) 0.06396(14) Uani 1 1 d . . . . .
N3 N 0.3630(4) 0.2820(5) 0.25570(17) 0.0440(9) Uani 1 1 d . . . . .
N1 N 0.5111(4) 0.4494(5) 0.27009(18) 0.0483(10) Uani 1 1 d . . . . .
C8 C 0.5037(4) 0.3994(6) 0.2139(2) 0.0420(10) Uani 1 1 d . . . . .
N4 N 0.2747(4) 0.0077(5) 0.06360(17) 0.0470(9) Uani 1 1 d . . . . .
N2 N 0.4263(4) 0.3785(6) 0.29654(18) 0.0507(10) Uani 1 1 d . . . . .
C5 C 0.5900(5) 0.4567(6) 0.1755(2) 0.0462(11) Uani 1 1 d . . . . .
C4 C 0.7182(5) 0.4710(8) 0.1951(3) 0.0615(14) Uani 1 1 d . . . . .
H4 H 0.751255 0.439062 0.232529 0.074 Uiso 1 1 calc R . . . .
C6 C 0.5433(6) 0.4985(8) 0.1189(2) 0.0606(14) Uani 1 1 d . . . . .
H6 H 0.457923 0.487747 0.104797 0.073 Uiso 1 1 calc R . . . .
C9 C 0.4057(4) 0.2872(6) 0.2041(2) 0.0418(10) Uani 1 1 d . . . . .
C7 C 0.6247(7) 0.5569(9) 0.0831(3) 0.0696(17) Uani 1 1 d . . . . .
H7 H 0.593267 0.582568 0.044817 0.084 Uiso 1 1 calc R . . . .
C2 C 0.7526(7) 0.5774(8) 0.1036(3) 0.0669(16) Uani 1 1 d . . . . .
C11 C 0.2576(6) 0.1870(8) 0.2706(3) 0.0632(15) Uani 1 1 d . . . . .
H11A H 0.267248 0.073841 0.260866 0.095 Uiso 1 1 calc GR . . . .
H11B H 0.180213 0.228383 0.249411 0.095 Uiso 1 1 calc GR . . . .
H11C H 0.256115 0.196438 0.311296 0.095 Uiso 1 1 calc GR . . . .
C3 C 0.7967(6) 0.5323(9) 0.1594(3) 0.0684(16) Uani 1 1 d . . . . .
H3 H 0.882058 0.543188 0.173551 0.082 Uiso 1 1 calc R . . . .
C10 C 0.5915(6) 0.5752(9) 0.3023(3) 0.0717(18) Uani 1 1 d . . . . .
H10A H 0.668402 0.525787 0.320794 0.108 Uiso 1 1 calc GR . . . .
H10B H 0.548524 0.623248 0.330962 0.108 Uiso 1 1 calc GR . . . .
H10C H 0.610032 0.658800 0.276063 0.108 Uiso 1 1 calc GR . . . .
C13 C 0.1308(9) -0.1825(11) 0.0123(3) 0.093(3) Uani 1 1 d . . . . .
H13 H 0.059447 -0.247108 0.011461 0.112 Uiso 1 1 calc R . . . .
C12 C 0.1720(7) -0.0837(10) 0.0595(3) 0.076(2) Uani 1 1 d . . . . .
H12 H 0.125596 -0.081348 0.089651 0.091 Uiso 1 1 calc R . . . .
C14 C 0.1948(7) -0.1845(9) -0.0326(3) 0.0746(18) Uani 1 1 d . . . . .
H14 H 0.168629 -0.250205 -0.064741 0.089 Uiso 1 1 calc R . . . .
C16 C 0.3349(6) 0.0059(10) 0.0186(3) 0.0738(19) Uani 1 1 d . . . . .
H16 H 0.405629 0.071945 0.019691 0.089 Uiso 1 1 calc R . . . .
C1 C 0.8396(8) 0.6459(11) 0.0656(4) 0.103(3) Uani 1 1 d . . . . .
H1A H 0.811927 0.611906 0.026436 0.155 Uiso 1 1 calc GR . . . .
H1B H 0.923247 0.606204 0.078514 0.155 Uiso 1 1 calc GR . . . .
H1C H 0.839112 0.763558 0.067681 0.155 Uiso 1 1 calc GR . . . .
C15 C 0.2978(7) -0.0889(11) -0.0298(3) 0.087(2) Uani 1 1 d . . . . .
H15 H 0.343423 -0.087043 -0.060191 0.105 Uiso 1 1 calc R . . . .


_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 I2 2.5935(5) . ?
Pd1 I1 2.6107(5) . ?
Pd1 N4 2.100(4) . ?
Pd1 C9 1.968(5) . ?
N3 N2 1.337(6) . ?
N3 C9 1.363(6) . ?
N3 C11 1.464(7) . ?
N1 C8 1.368(6) . ?
N1 N2 1.319(6) . ?
N1 C10 1.470(7) . ?
C8 C5 1.473(7) . ?
C8 C9 1.387(7) . ?
N4 C12 1.325(8) . ?
N4 C16 1.327(7) . ?
C5 C4 1.388(7) . ?
C5 C6 1.384(8) . ?
C4 C3 1.377(8) . ?
C6 C7 1.393(9) . ?
C7 C2 1.394(10) . ?
C2 C3 1.368(10) . ?
C2 C1 1.501(9) . ?
C13 C12 1.383(9) . ?
C13 C14 1.349(10) . ?
C14 C15 1.349(10) . ?
C16 C15 1.376(9) . ?

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
I2 Pd1 I1 176.52(2) . . ?
N4 Pd1 I2 90.46(12) . . ?
N4 Pd1 I1 91.59(12) . . ?
C9 Pd1 I2 87.89(14) . . ?
C9 Pd1 I1 90.13(14) . . ?
C9 Pd1 N4 177.77(17) . . ?
N2 N3 C9 114.2(4) . . ?
N2 N3 C11 117.8(4) . . ?
C9 N3 C11 128.0(4) . . ?
C8 N1 C10 129.8(5) . . ?
N2 N1 C8 112.7(4) . . ?
N2 N1 C10 117.4(4) . . ?
N1 C8 C5 123.4(4) . . ?
N1 C8 C9 106.3(4) . . ?
C9 C8 C5 130.3(4) . . ?
C12 N4 Pd1 122.5(4) . . ?
C12 N4 C16 116.5(5) . . ?
C16 N4 Pd1 121.0(4) . . ?
N1 N2 N3 103.5(4) . . ?
C4 C5 C8 121.2(5) . . ?
C6 C5 C8 119.9(5) . . ?
C6 C5 C4 118.9(5) . . ?
C3 C4 C5 120.4(6) . . ?
C5 C6 C7 119.7(6) . . ?
N3 C9 Pd1 124.5(4) . . ?
N3 C9 C8 103.4(4) . . ?
C8 C9 Pd1 132.1(3) . . ?
C6 C7 C2 121.2(6) . . ?
C7 C2 C1 121.2(7) . . ?
C3 C2 C7 117.9(6) . . ?
C3 C2 C1 120.9(7) . . ?
C2 C3 C4 121.7(6) . . ?
C14 C13 C12 119.6(7) . . ?
N4 C12 C13 122.8(6) . . ?
C13 C14 C15 118.4(6) . . ?
N4 C16 C15 123.2(6) . . ?
C14 C15 C16 119.5(6) . . ?

_olex2_date_sample_data_collection 2017-08-01
_olex2_submission_special_instructions 'No special instructions were received'
