# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 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. 
# 
#######################################################################

data_o+p212121
_database_code_depnum_ccdc_archive 'CCDC 1005188'
_audit_update_record             
;
2014-05-25 deposited with the CCDC.
2016-08-23 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT026_op212121            
;
PROBLEM: Ratio Observed / Unique Reflections too Low ....         20 %     
RESPONSE: The crystal used for data collection was not good in quality. 
Several data for different crystals and different samples were collected. 
The data reported here is the best.
;
# end Validation Reply Form

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H15 N3 O'
_chemical_formula_sum            'C21 H15 N3 O'
_chemical_formula_weight         325.36

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'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   'P2(1)2(1)2(1) '

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

_cell_length_a                   4.7910(10)
_cell_length_b                   16.125(4)
_cell_length_c                   20.850(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1610.8(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       irregular
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.342
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             680
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      298(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  'Stoe IPDS-II'
_diffrn_measurement_method       'rotation method'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8092
_diffrn_reflns_av_R_equivalents  0.1157
_diffrn_reflns_av_sigmaI/netI    0.4477
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         1.95
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2795
_reflns_number_gt                558
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       'X-AREA (Stoe & Cie, 2005)'
_computing_cell_refinement       'X-AREA (Stoe & Cie, 2005)'
_computing_data_reduction        'X-AREA (Stoe & Cie, 2005)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'

_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)+(0.0000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_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         2795
_refine_ls_number_parameters     226
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2174
_refine_ls_R_factor_gt           0.0329
_refine_ls_wR_factor_ref         0.0458
_refine_ls_wR_factor_gt          0.0278
_refine_ls_goodness_of_fit_ref   0.827
_refine_ls_restrained_S_all      0.427
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.002

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
O1 O -0.2224(10) 0.4748(2) 0.52006(17) 0.0705(14) Uani 1 1 d . . .
H1 H -0.1225 0.4705 0.5518 0.106 Uiso 1 1 calc R . .
N1 N 0.1499(11) 0.1125(3) 0.2377(3) 0.0479(16) Uani 1 1 d . . .
C7 C 0.2182(12) 0.1668(3) 0.3433(3) 0.0446(18) Uani 1 1 d . . .
H7 H 0.3097 0.1636 0.3826 0.053 Uiso 1 1 calc R . .
C1 C 0.4768(13) 0.0398(3) 0.3055(3) 0.0388(17) Uani 1 1 d . . .
C6 C 0.2709(13) 0.1084(3) 0.2952(3) 0.0396(17) Uani 1 1 d . . .
N2 N 0.5692(11) 0.0255(3) 0.3648(2) 0.0499(16) Uani 1 1 d . . .
C8 C 0.0278(13) 0.2294(4) 0.3315(3) 0.0428(18) Uani 1 1 d . . .
C9 C -0.1017(11) 0.2328(3) 0.2733(3) 0.0392(16) Uani 1 1 d . . .
H9 H -0.2303 0.2745 0.2644 0.047 Uiso 1 1 calc R . .
C19 C -0.1498(15) 0.4132(4) 0.4751(3) 0.0492(19) Uani 1 1 d . . .
C16 C -0.0358(13) 0.2927(4) 0.3827(3) 0.0417(18) Uani 1 1 d . . .
C10 C -0.0389(14) 0.1733(4) 0.2276(3) 0.0449(18) Uani 1 1 d . . .
C18 C 0.0543(15) 0.3586(4) 0.4859(3) 0.067(2) Uani 1 1 d . . .
H18 H 0.1566 0.3605 0.5238 0.080 Uiso 1 1 calc R . .
N3 N -0.3421(13) 0.2401(3) 0.1507(3) 0.0729(19) Uani 1 1 d . . .
C4 C 0.8611(14) -0.0824(4) 0.3221(4) 0.069(2) Uani 1 1 d . . .
H4 H 0.9924 -0.1239 0.3291 0.083 Uiso 1 1 calc R . .
C2 C 0.5683(13) -0.0056(3) 0.2526(3) 0.0529(19) Uani 1 1 d . . .
H2 H 0.5001 0.0054 0.2118 0.063 Uiso 1 1 calc R . .
C3 C 0.7622(14) -0.0671(4) 0.2626(3) 0.062(2) Uani 1 1 d . . .
H3 H 0.8258 -0.0984 0.2281 0.074 Uiso 1 1 calc R . .
C11 C -0.1691(14) 0.1751(4) 0.1634(3) 0.0478(18) Uani 1 1 d . . .
C12 C -0.1266(17) 0.1115(4) 0.1193(3) 0.072(3) Uani 1 1 d . . .
H12 H -0.0042 0.0683 0.1283 0.087 Uiso 1 1 calc R . .
C21 C -0.2425(14) 0.3529(4) 0.3737(3) 0.067(2) Uani 1 1 d . . .
H21 H -0.3476 0.3521 0.3362 0.080 Uiso 1 1 calc R . .
C5 C 0.7612(15) -0.0342(3) 0.3731(3) 0.063(2) Uani 1 1 d . . .
H5 H 0.8302 -0.0440 0.4141 0.075 Uiso 1 1 calc R . .
C20 C -0.2950(14) 0.4138(4) 0.4191(3) 0.063(2) Uani 1 1 d . . .
H20 H -0.4281 0.4545 0.4113 0.076 Uiso 1 1 calc R . .
C13 C -0.2700(16) 0.1142(4) 0.0621(4) 0.073(3) Uani 1 1 d . . .
H13 H -0.2473 0.0713 0.0327 0.087 Uiso 1 1 calc R . .
C17 C 0.1106(14) 0.2993(4) 0.4397(4) 0.070(2) Uani 1 1 d . . .
H17 H 0.2544 0.2618 0.4474 0.084 Uiso 1 1 calc R . .
C15 C -0.4735(14) 0.2388(4) 0.0927(4) 0.081(2) Uani 1 1 d . . .
H15 H -0.5919 0.2829 0.0834 0.097 Uiso 1 1 calc R . .
C14 C -0.4472(16) 0.1792(5) 0.0475(3) 0.070(2) Uani 1 1 d . . .
H14 H -0.5429 0.1818 0.0088 0.084 Uiso 1 1 calc R . .


_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
O1 C19 1.409(6) . ?
O1 H1 0.8200 . ?
N1 C6 1.334(7) . ?
N1 C10 1.351(6) . ?
C7 C8 1.382(7) . ?
C7 C6 1.399(7) . ?
C7 H7 0.9300 . ?
C1 N2 1.334(6) . ?
C1 C2 1.394(7) . ?
C1 C6 1.498(7) . ?
N2 C5 1.343(7) . ?
C8 C9 1.366(7) . ?
C8 C16 1.508(7) . ?
C9 C10 1.384(7) . ?
C9 H9 0.9300 . ?
C19 C18 1.335(8) . ?
C19 C20 1.359(7) . ?
C16 C17 1.383(8) . ?
C16 C21 1.400(7) . ?
C10 C11 1.478(7) . ?
C18 C17 1.386(7) . ?
C18 H18 0.9300 . ?
N3 C15 1.362(8) . ?
N3 C11 1.362(7) . ?
C4 C3 1.352(7) . ?
C4 C5 1.400(8) . ?
C4 H4 0.9300 . ?
C2 C3 1.375(7) . ?
C2 H2 0.9300 . ?
C3 H3 0.9300 . ?
C11 C12 1.392(8) . ?
C12 C13 1.377(8) . ?
C12 H12 0.9300 . ?
C21 C20 1.386(7) . ?
C21 H21 0.9300 . ?
C5 H5 0.9300 . ?
C20 H20 0.9300 . ?
C13 C14 1.383(8) . ?
C13 H13 0.9300 . ?
C17 H17 0.9300 . ?
C15 C14 1.352(8) . ?
C15 H15 0.9300 . ?
C14 H14 0.9300 . ?

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
C19 O1 H1 109.5 . . ?
C6 N1 C10 117.8(5) . . ?
C8 C7 C6 118.9(6) . . ?
C8 C7 H7 120.6 . . ?
C6 C7 H7 120.6 . . ?
N2 C1 C2 122.5(6) . . ?
N2 C1 C6 118.6(6) . . ?
C2 C1 C6 118.8(6) . . ?
N1 C6 C7 122.2(6) . . ?
N1 C6 C1 116.8(6) . . ?
C7 C6 C1 120.9(6) . . ?
C5 N2 C1 118.0(6) . . ?
C9 C8 C7 119.2(6) . . ?
C9 C8 C16 120.7(6) . . ?
C7 C8 C16 120.1(6) . . ?
C8 C9 C10 119.0(5) . . ?
C8 C9 H9 120.5 . . ?
C10 C9 H9 120.5 . . ?
C18 C19 C20 121.7(6) . . ?
C18 C19 O1 122.2(7) . . ?
C20 C19 O1 116.1(6) . . ?
C17 C16 C21 114.9(6) . . ?
C17 C16 C8 123.9(6) . . ?
C21 C16 C8 121.2(6) . . ?
N1 C10 C9 122.8(6) . . ?
N1 C10 C11 116.0(6) . . ?
C9 C10 C11 121.2(6) . . ?
C19 C18 C17 118.7(7) . . ?
C19 C18 H18 120.7 . . ?
C17 C18 H18 120.7 . . ?
C15 N3 C11 116.3(6) . . ?
C3 C4 C5 118.4(6) . . ?
C3 C4 H4 120.8 . . ?
C5 C4 H4 120.8 . . ?
C3 C2 C1 118.2(6) . . ?
C3 C2 H2 120.9 . . ?
C1 C2 H2 120.9 . . ?
C4 C3 C2 120.5(7) . . ?
C4 C3 H3 119.8 . . ?
C2 C3 H3 119.8 . . ?
N3 C11 C12 121.8(7) . . ?
N3 C11 C10 116.6(6) . . ?
C12 C11 C10 121.5(6) . . ?
C13 C12 C11 118.4(7) . . ?
C13 C12 H12 120.8 . . ?
C11 C12 H12 120.8 . . ?
C16 C21 C20 121.9(6) . . ?
C16 C21 H21 119.1 . . ?
C20 C21 H21 119.1 . . ?
N2 C5 C4 122.4(6) . . ?
N2 C5 H5 118.8 . . ?
C4 C5 H5 118.8 . . ?
C19 C20 C21 119.3(6) . . ?
C19 C20 H20 120.4 . . ?
C21 C20 H20 120.4 . . ?
C12 C13 C14 121.3(8) . . ?
C12 C13 H13 119.3 . . ?
C14 C13 H13 119.3 . . ?
C16 C17 C18 123.5(7) . . ?
C16 C17 H17 118.3 . . ?
C18 C17 H17 118.3 . . ?
C14 C15 N3 125.8(7) . . ?
C14 C15 H15 117.1 . . ?
N3 C15 H15 117.1 . . ?
C15 C14 C13 116.3(8) . . ?
C15 C14 H14 121.8 . . ?
C13 C14 H14 121.8 . . ?

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 N1 C6 C7 -3.1(9) . . . . ?
C10 N1 C6 C1 179.3(5) . . . . ?
C8 C7 C6 N1 2.0(9) . . . . ?
C8 C7 C6 C1 179.6(5) . . . . ?
N2 C1 C6 N1 -169.6(6) . . . . ?
C2 C1 C6 N1 11.5(7) . . . . ?
N2 C1 C6 C7 12.7(8) . . . . ?
C2 C1 C6 C7 -166.1(6) . . . . ?
C2 C1 N2 C5 1.1(9) . . . . ?
C6 C1 N2 C5 -177.7(5) . . . . ?
C6 C7 C8 C9 -0.5(8) . . . . ?
C6 C7 C8 C16 179.3(5) . . . . ?
C7 C8 C9 C10 0.1(8) . . . . ?
C16 C8 C9 C10 -179.7(5) . . . . ?
C9 C8 C16 C17 -171.9(6) . . . . ?
C7 C8 C16 C17 8.3(9) . . . . ?
C9 C8 C16 C21 4.6(8) . . . . ?
C7 C8 C16 C21 -175.2(6) . . . . ?
C6 N1 C10 C9 2.7(9) . . . . ?
C6 N1 C10 C11 -179.6(5) . . . . ?
C8 C9 C10 N1 -1.3(9) . . . . ?
C8 C9 C10 C11 -178.8(6) . . . . ?
C20 C19 C18 C17 -2.6(11) . . . . ?
O1 C19 C18 C17 179.1(6) . . . . ?
N2 C1 C2 C3 -0.3(9) . . . . ?
C6 C1 C2 C3 178.5(6) . . . . ?
C5 C4 C3 C2 0.0(11) . . . . ?
C1 C2 C3 C4 -0.3(10) . . . . ?
C15 N3 C11 C12 0.7(10) . . . . ?
C15 N3 C11 C10 -176.4(6) . . . . ?
N1 C10 C11 N3 -174.7(6) . . . . ?
C9 C10 C11 N3 3.1(9) . . . . ?
N1 C10 C11 C12 8.2(9) . . . . ?
C9 C10 C11 C12 -174.1(6) . . . . ?
N3 C11 C12 C13 -1.6(11) . . . . ?
C10 C11 C12 C13 175.4(7) . . . . ?
C17 C16 C21 C20 -0.4(10) . . . . ?
C8 C16 C21 C20 -177.1(6) . . . . ?
C1 N2 C5 C4 -1.4(9) . . . . ?
C3 C4 C5 N2 0.8(11) . . . . ?
C18 C19 C20 C21 4.2(11) . . . . ?
O1 C19 C20 C21 -177.4(6) . . . . ?
C16 C21 C20 C19 -2.7(11) . . . . ?
C11 C12 C13 C14 1.7(11) . . . . ?
C21 C16 C17 C18 2.1(10) . . . . ?
C8 C16 C17 C18 178.7(6) . . . . ?
C19 C18 C17 C16 -0.7(11) . . . . ?
C11 N3 C15 C14 0.1(12) . . . . ?
N3 C15 C14 C13 -0.1(12) . . . . ?
C12 C13 C14 C15 -0.8(11) . . . . ?

_diffrn_measured_fraction_theta_max 0.991
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.991
_refine_diff_density_max         0.102
_refine_diff_density_min         -0.157
_refine_diff_density_rms         0.027
####################################################################### 
# 
# 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_fa14_9cu
_database_code_depnum_ccdc_archive 'CCDC 1479098'
_audit_update_record             
;
2016-05-10 deposited with the CCDC.
2016-08-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
;
(4'-(4-Hydroxyphenyl)-2,2':6',2''-terpyridine-κ³N)chloridopalladium(II)
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H15 Cl N3 O Pd, Cl, H2 O, 0.8O'
_chemical_formula_sum            'C21 H17 Cl2 N3 O2.80 Pd'
_chemical_formula_weight         533.48

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Pd Pd 0.1215 3.9337 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      tetragonal
_space_group_IT_number           85
_space_group_name_H-M_alt        'P 4/n'
_space_group_name_Hall           '-P 4a'

_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+1/2, z'
'-y+1/2, x, z'
'y, -x+1/2, z'
'-x, -y, -z'
'x-1/2, y-1/2, -z'
'y-1/2, -x, -z'
'-y, x-1/2, -z'

_cell_length_a                   29.3162(6)
_cell_length_b                   29.3162(6)
_cell_length_c                   5.0991(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4382.4(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    8614
_cell_measurement_theta_min      4.3190
_cell_measurement_theta_max      75.9910

_exptl_crystal_description       needle
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.617
_exptl_crystal_F_000             2131.2
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.420
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    9.301
_shelx_estimated_absorpt_T_min   0.112
_shelx_estimated_absorpt_T_max   0.456
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.26710
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   'CrysAlisPro, Agilent (2013)'

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'SuperNova (Cu) X-ray Source'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 5.1725
_diffrn_standards_number         0
_diffrn_reflns_number            17060
_diffrn_reflns_av_unetI/netI     0.0380
_diffrn_reflns_av_R_equivalents  0.0595
_diffrn_reflns_limit_h_min       -36
_diffrn_reflns_limit_h_max       35
_diffrn_reflns_limit_k_min       -36
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_theta_min         4.266
_diffrn_reflns_theta_max         76.306
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4561
_reflns_number_gt                4095
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'CrysAlisPro, Agilent (2013)'
_computing_cell_refinement       'CrysAlisPro, Agilent (2013)'
_computing_data_reduction        'CrysAlisPro, Agilent (2013)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015a)'
_computing_structure_refinement  
;
SHELXL-2014/7 (Sheldrick, 2015b) & TITAN (Hunter & Simpson, 1999)
;
_computing_molecular_graphics    'Mercury (Macrae et al., 2008)'
_computing_publication_material  
;
SHELXL-2014 (Sheldrick, 2008), enCIFer (Allen et al., 2004), 
PLATON (Spek, 2009),  PublCIF (Westrip 2010), WINGX (Farrugia 1997)
;

_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)+(0.1114P)²+123.5093P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4561
_refine_ls_number_parameters     288
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.1118
_refine_ls_R_factor_gt           0.1059
_refine_ls_wR_factor_ref         0.2936
_refine_ls_wR_factor_gt          0.2899
_refine_ls_goodness_of_fit_ref   1.188
_refine_ls_restrained_S_all      1.188
_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 0.57555(3) 0.46076(3) 1.45440(16) 0.0242(3) Uani 1 1 d . . . . .
Cl1 Cl 0.52556(9) 0.43586(9) 1.7684(5) 0.0294(6) Uani 1 1 d . . . . .
N1 N 0.5744(3) 0.5283(3) 1.5338(18) 0.0229(18) Uani 1 1 d . . . . .
C2 C 0.5501(4) 0.5498(4) 1.720(2) 0.028(2) Uani 1 1 d . . . . .
H2 H 0.5309 0.5324 1.8310 0.034 Uiso 1 1 calc R U . . .
C3 C 0.5523(4) 0.5963(4) 1.754(2) 0.027(2) Uani 1 1 d . . . . .
H3 H 0.5351 0.6105 1.8894 0.033 Uiso 1 1 calc R U . . .
C4 C 0.5797(4) 0.6223(4) 1.593(2) 0.027(2) Uani 1 1 d . . . . .
H4 H 0.5810 0.6545 1.6123 0.033 Uiso 1 1 calc R U . . .
C5 C 0.6052(4) 0.6003(4) 1.400(2) 0.025(2) Uani 1 1 d . . . . .
H5 H 0.6244 0.6174 1.2862 0.030 Uiso 1 1 calc R U . . .
C6 C 0.6025(3) 0.5536(3) 1.3760(19) 0.0203(19) Uani 1 1 d . . . . .
N2 N 0.6188(3) 0.4814(3) 1.1902(17) 0.0224(18) Uani 1 1 d . . . . .
C7 C 0.6276(3) 0.5266(3) 1.177(2) 0.021(2) Uani 1 1 d . . . . .
C8 C 0.6586(4) 0.5423(4) 0.995(2) 0.023(2) Uani 1 1 d . . . . .
H8 H 0.6657 0.5739 0.9859 0.027 Uiso 1 1 calc R U . . .
C9 C 0.6797(3) 0.5112(4) 0.824(2) 0.023(2) Uani 1 1 d . . . . .
C10 C 0.6687(3) 0.4648(4) 0.845(2) 0.027(2) Uani 1 1 d . . . . .
H10 H 0.6824 0.4432 0.7311 0.032 Uiso 1 1 calc R U . . .
C11 C 0.6377(3) 0.4507(4) 1.032(2) 0.026(2) Uani 1 1 d . . . . .
C12 C 0.6202(4) 0.4043(4) 1.083(2) 0.026(2) Uani 1 1 d . . . . .
C13 C 0.6319(4) 0.3668(4) 0.926(2) 0.032(2) Uani 1 1 d . . . . .
H13 H 0.6525 0.3700 0.7832 0.039 Uiso 1 1 calc R U . . .
C14 C 0.6122(5) 0.3247(4) 0.986(3) 0.041(3) Uani 1 1 d . . . . .
H14 H 0.6192 0.2986 0.8821 0.049 Uiso 1 1 calc R U . . .
C15 C 0.5827(5) 0.3209(4) 1.194(3) 0.040(3) Uani 1 1 d . . . . .
H15 H 0.5700 0.2922 1.2396 0.048 Uiso 1 1 calc R U . . .
C16 C 0.5721(4) 0.3591(4) 1.334(3) 0.035(3) Uani 1 1 d . . . . .
H16 H 0.5508 0.3566 1.4737 0.042 Uiso 1 1 calc R U . . .
N3 N 0.5903(3) 0.4001(3) 1.2818(17) 0.0252(18) Uani 1 1 d . . . . .
C17 C 0.7125(3) 0.5272(4) 0.621(2) 0.023(2) Uani 1 1 d . . . . .
C18 C 0.7204(4) 0.5736(4) 0.580(2) 0.028(2) Uani 1 1 d . . . . .
H18 H 0.7049 0.5954 0.6846 0.033 Uiso 1 1 calc R U . . .
C19 C 0.7508(4) 0.5885(4) 0.388(2) 0.031(2) Uani 1 1 d . . . . .
H19 H 0.7553 0.6203 0.3597 0.037 Uiso 1 1 calc R U . . .
C20 C 0.7747(3) 0.5570(4) 0.238(2) 0.028(2) Uani 1 1 d . . . . .
O20 O 0.8048(3) 0.5692(3) 0.0499(17) 0.0355(19) Uani 1 1 d . . . . .
H20 H 0.8041 0.5977 0.0300 0.053 Uiso 1 1 calc R U . . .
C21 C 0.7680(4) 0.5108(4) 0.280(2) 0.029(2) Uani 1 1 d . . . . .
H21 H 0.7845 0.4891 0.1793 0.035 Uiso 1 1 calc R U . . .
C22 C 0.7372(4) 0.4961(4) 0.470(2) 0.026(2) Uani 1 1 d . . . . .
H22 H 0.7329 0.4643 0.4971 0.031 Uiso 1 1 calc R U . . .
Cl3 Cl 0.72022(14) 0.37423(16) 1.4375(11) 0.0255(11) Uani 0.5 1 d . . P . .
Cl2 Cl 0.82773(16) 0.66633(17) -0.0115(9) 0.0236(9) Uani 0.5 1 d . . P . .
O1W O 0.7977(4) 0.7033(3) -0.502(2) 0.050(3) Uani 1 1 d D . . . .
H11W H 0.813(6) 0.682(5) -0.56(4) 0.075 Uiso 1 1 d D U . . .
H12W H 0.799(7) 0.729(3) -0.56(4) 0.075 Uiso 1 1 d D U . . .
O2W O 0.7338(7) 0.3157(7) 0.956(6) 0.109(8) Uani 0.8 1 d . . P . .


_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 Cl1 2.290(3) . y
Pd1 N1 2.020(9) . y
Pd1 N2 1.946(9) . y
Pd1 N3 2.032(9) . y
N1 C2 1.343(14) . ?
N1 C6 1.370(13) . ?
C2 C3 1.375(16) . ?
C2 H2 0.9500 . ?
C3 C4 1.380(15) . ?
C3 H3 0.9500 . ?
C4 C5 1.394(15) . ?
C4 H4 0.9500 . ?
C5 C6 1.377(15) . ?
C5 H5 0.9500 . ?
C6 C7 1.482(14) . ?
N2 C11 1.328(14) . ?
N2 C7 1.353(14) . ?
C7 C8 1.377(15) . ?
C8 C9 1.408(14) . ?
C8 H8 0.9500 . ?
C9 C10 1.401(16) . ?
C9 C17 1.488(14) . ?
C10 C11 1.381(16) . ?
C10 H10 0.9500 . ?
C11 C12 1.479(16) . ?
C12 N3 1.344(14) . ?
C12 C13 1.403(16) . ?
C13 C14 1.396(18) . ?
C13 H13 0.9500 . ?
C14 C15 1.37(2) . ?
C14 H14 0.9500 . ?
C15 C16 1.365(18) . ?
C15 H15 0.9500 . ?
C16 N3 1.340(15) . ?
C16 H16 0.9500 . ?
C17 C18 1.396(16) . ?
C17 C22 1.397(15) . ?
C18 C19 1.394(16) . ?
C18 H18 0.9500 . ?
C19 C20 1.389(16) . ?
C19 H19 0.9500 . ?
C20 O20 1.352(14) . ?
C20 C21 1.385(17) . ?
O20 H20 0.8400 . ?
C21 C22 1.392(15) . ?
C21 H21 0.9500 . ?
C22 H22 0.9500 . ?
O1W H11W 0.80(2) . ?
O1W H12W 0.80(2) . ?

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
N2 Pd1 N1 81.1(4) . . y
N2 Pd1 N3 80.4(4) . . y
N1 Pd1 N3 161.5(4) . . y
N2 Pd1 Cl1 179.1(3) . . y
N1 Pd1 Cl1 99.3(3) . . y
N3 Pd1 Cl1 99.2(3) . . y
C2 N1 C6 118.5(9) . . ?
C2 N1 Pd1 127.7(7) . . ?
C6 N1 Pd1 113.8(7) . . ?
N1 C2 C3 122.2(10) . . ?
N1 C2 H2 118.9 . . ?
C3 C2 H2 118.9 . . ?
C2 C3 C4 119.8(10) . . ?
C2 C3 H3 120.1 . . ?
C4 C3 H3 120.1 . . ?
C3 C4 C5 118.5(10) . . ?
C3 C4 H4 120.7 . . ?
C5 C4 H4 120.7 . . ?
C6 C5 C4 119.4(10) . . ?
C6 C5 H5 120.3 . . ?
C4 C5 H5 120.3 . . ?
N1 C6 C5 121.5(9) . . ?
N1 C6 C7 114.3(9) . . ?
C5 C6 C7 124.2(9) . . ?
C11 N2 C7 123.6(9) . . ?
C11 N2 Pd1 118.8(8) . . ?
C7 N2 Pd1 117.6(7) . . ?
N2 C7 C8 119.1(9) . . ?
N2 C7 C6 113.2(9) . . ?
C8 C7 C6 127.7(10) . . ?
C7 C8 C9 119.5(10) . . ?
C7 C8 H8 120.2 . . ?
C9 C8 H8 120.2 . . ?
C10 C9 C8 118.6(10) . . ?
C10 C9 C17 120.7(9) . . ?
C8 C9 C17 120.7(10) . . ?
C11 C10 C9 119.7(10) . . ?
C11 C10 H10 120.2 . . ?
C9 C10 H10 120.2 . . ?
N2 C11 C10 119.4(10) . . ?
N2 C11 C12 111.8(10) . . ?
C10 C11 C12 128.7(10) . . ?
N3 C12 C13 121.2(10) . . ?
N3 C12 C11 116.3(10) . . ?
C13 C12 C11 122.4(10) . . ?
C14 C13 C12 117.8(11) . . ?
C14 C13 H13 121.1 . . ?
C12 C13 H13 121.1 . . ?
C15 C14 C13 120.0(12) . . ?
C15 C14 H14 120.0 . . ?
C13 C14 H14 120.0 . . ?
C16 C15 C14 118.8(12) . . ?
C16 C15 H15 120.6 . . ?
C14 C15 H15 120.6 . . ?
N3 C16 C15 122.7(12) . . ?
N3 C16 H16 118.6 . . ?
C15 C16 H16 118.6 . . ?
C16 N3 C12 119.4(10) . . ?
C16 N3 Pd1 127.8(8) . . ?
C12 N3 Pd1 112.6(7) . . ?
C18 C17 C22 117.9(10) . . ?
C18 C17 C9 121.4(9) . . ?
C22 C17 C9 120.7(10) . . ?
C19 C18 C17 121.2(10) . . ?
C19 C18 H18 119.4 . . ?
C17 C18 H18 119.4 . . ?
C20 C19 C18 120.0(11) . . ?
C20 C19 H19 120.0 . . ?
C18 C19 H19 120.0 . . ?
O20 C20 C21 117.5(10) . . ?
O20 C20 C19 122.9(11) . . ?
C21 C20 C19 119.6(10) . . ?
C20 O20 H20 109.5 . . ?
C20 C21 C22 120.2(11) . . ?
C20 C21 H21 119.9 . . ?
C22 C21 H21 119.9 . . ?
C21 C22 C17 121.1(10) . . ?
C21 C22 H22 119.4 . . ?
C17 C22 H22 119.4 . . ?
H11W O1W H12W 125(10) . . ?

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
C6 N1 C2 C3 0.7(16) . . . . ?
Pd1 N1 C2 C3 180.0(8) . . . . ?
N1 C2 C3 C4 0.9(17) . . . . ?
C2 C3 C4 C5 -1.2(17) . . . . ?
C3 C4 C5 C6 0.1(16) . . . . ?
C2 N1 C6 C5 -1.8(15) . . . . ?
Pd1 N1 C6 C5 178.8(8) . . . . ?
C2 N1 C6 C7 -179.9(9) . . . . ?
Pd1 N1 C6 C7 0.6(11) . . . . ?
C4 C5 C6 N1 1.4(15) . . . . ?
C4 C5 C6 C7 179.4(10) . . . . ?
C11 N2 C7 C8 -1.5(15) . . . . ?
Pd1 N2 C7 C8 179.0(7) . . . . ?
C11 N2 C7 C6 -179.7(9) . . . . ?
Pd1 N2 C7 C6 0.8(11) . . . . ?
N1 C6 C7 N2 -1.0(12) . . . . ?
C5 C6 C7 N2 -179.0(9) . . . . ?
N1 C6 C7 C8 -178.9(10) . . . . ?
C5 C6 C7 C8 3.0(16) . . . . ?
N2 C7 C8 C9 1.3(15) . . . . ?
C6 C7 C8 C9 179.1(9) . . . . ?
C7 C8 C9 C10 -0.6(15) . . . . ?
C7 C8 C9 C17 178.6(9) . . . . ?
C8 C9 C10 C11 0.0(15) . . . . ?
C17 C9 C10 C11 -179.2(10) . . . . ?
C7 N2 C11 C10 1.0(15) . . . . ?
Pd1 N2 C11 C10 -179.6(7) . . . . ?
C7 N2 C11 C12 -177.5(9) . . . . ?
Pd1 N2 C11 C12 2.0(11) . . . . ?
C9 C10 C11 N2 -0.2(15) . . . . ?
C9 C10 C11 C12 178.0(10) . . . . ?
N2 C11 C12 N3 -2.5(13) . . . . ?
C10 C11 C12 N3 179.3(10) . . . . ?
N2 C11 C12 C13 174.1(10) . . . . ?
C10 C11 C12 C13 -4.2(17) . . . . ?
N3 C12 C13 C14 -1.4(17) . . . . ?
C11 C12 C13 C14 -177.8(11) . . . . ?
C12 C13 C14 C15 -0.5(19) . . . . ?
C13 C14 C15 C16 2(2) . . . . ?
C14 C15 C16 N3 -2(2) . . . . ?
C15 C16 N3 C12 0.4(18) . . . . ?
C15 C16 N3 Pd1 176.0(10) . . . . ?
C13 C12 N3 C16 1.4(16) . . . . ?
C11 C12 N3 C16 178.0(10) . . . . ?
C13 C12 N3 Pd1 -174.8(8) . . . . ?
C11 C12 N3 Pd1 1.8(12) . . . . ?
C10 C9 C17 C18 173.6(10) . . . . ?
C8 C9 C17 C18 -5.5(15) . . . . ?
C10 C9 C17 C22 -8.0(15) . . . . ?
C8 C9 C17 C22 172.9(10) . . . . ?
C22 C17 C18 C19 2.2(16) . . . . ?
C9 C17 C18 C19 -179.3(10) . . . . ?
C17 C18 C19 C20 -1.6(17) . . . . ?
C18 C19 C20 O20 -179.6(10) . . . . ?
C18 C19 C20 C21 0.1(17) . . . . ?
O20 C20 C21 C22 -179.6(10) . . . . ?
C19 C20 C21 C22 0.7(17) . . . . ?
C20 C21 C22 C17 0.0(17) . . . . ?
C18 C17 C22 C21 -1.4(16) . . . . ?
C9 C17 C22 C21 -179.9(10) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O20 H20 Cl2 0.83(17) 2.14(17) 2.942(10) 160(17) 1_555
O1W H11W Cl2 0.82(16) 2.4(2) 2.950(11) 126(17) 1_554
O1W H12W O1W 0.80(2) 2.04(10) 2.769(15) 151(20) 3_655
C2 H2 Cl1 0.95 2.79 3.452(11) 128 5_669
C3 H3 Cl1 0.95 2.84 3.468(11) 125 5_669
C4 H4 O20 0.95 2.55 3.177(13) 123 4_567
C5 H5 Cl2 0.95 2.53 3.474(12) 171 4_566
C10 H10 Cl3 0.95 2.75 3.694(12) 174 1_554
C13 H13 Cl3 0.95 2.66 3.599(13) 171 1_554
C14 H14 Cl3 0.95 2.82 3.769(14) 171 8_657
C22 H22 Cl3 0.95 2.68 3.611(12) 165 1_554

_refine_diff_density_max         2.714
_refine_diff_density_min         -1.387
_refine_diff_density_rms         0.267

