# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_2-(Phenylazo)azobenzene
_database_code_depnum_ccdc_archive 'CCDC 1031475'
_audit_update_record             
;
2014-10-29 deposited with the CCDC.
2015-02-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H14 N4'
_chemical_formula_sum            'C18 H14 N4'
_chemical_formula_weight         286.33

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'

_symmetry_cell_setting           MOnoclinic
_symmetry_space_group_name_H-M   P2(1)/c
_symmetry_space_group_name_Hall  -P2ybc
_symmetry_Int_Tables_number      14

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

_cell_length_a                   9.1369(2)
_cell_length_b                   17.8053(4)
_cell_length_c                   9.7509(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 108.4570(10)
_cell_angle_gamma                90.00
_cell_volume                     1504.73(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1228
_cell_measurement_theta_min      2.29
_cell_measurement_theta_max      27.48

_exptl_crystal_description       parallelopiped
_exptl_crystal_colour            Red
_exptl_crystal_size_max          0.58
_exptl_crystal_size_mid          0.45
_exptl_crystal_size_min          0.22
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.264
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             600
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.960
_exptl_absorpt_correction_T_max  0.981
_exptl_absorpt_process_details   'Sadabs(Sheldrick, 1996)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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  'CCD area-detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            23323
_diffrn_reflns_av_R_equivalents  0.0285
_diffrn_reflns_av_sigmaI/netI    0.0170
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.29
_diffrn_reflns_theta_max         27.48
_reflns_number_total             3445
_reflns_number_gt                2681
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'SMART APEX II (Bruker,2010)'
_computing_cell_refinement       'SMART APEX II'
_computing_data_reduction        'SAINT (Bruker,2000)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Ortep-3v2 for windows (Farrugia, 1997)'
_computing_publication_material  'PLATON (Spek, 2008)'

_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 > 2sigma(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)+(0.0523P)²+0.2049P] 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     SHELXL
_refine_ls_extinction_coef       0.0168(19)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3445
_refine_ls_number_parameters     200
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0536
_refine_ls_R_factor_gt           0.0407
_refine_ls_wR_factor_ref         0.1159
_refine_ls_wR_factor_gt          0.1059
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_restrained_S_all      1.041
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.71351(11) 0.04581(5) 1.00042(10) 0.0493(2) Uani 1 1 d . . .
N2 N 0.65131(11) 0.10653(5) 0.95169(10) 0.0498(3) Uani 1 1 d . . .
N3 N 0.47116(11) 0.21652(5) 0.79272(10) 0.0468(2) Uani 1 1 d . . .
N4 N 0.40522(12) 0.27325(5) 0.72764(11) 0.0524(3) Uani 1 1 d . . .
C1 C 0.59994(16) 0.06143(7) 1.19914(15) 0.0598(3) Uani 1 1 d . . .
H1 H 0.5483 0.1050 1.1583 0.072 Uiso 1 1 calc R . .
C2 C 0.58929(19) 0.03477(9) 1.32788(17) 0.0746(4) Uani 1 1 d . . .
H2 H 0.5304 0.0607 1.3746 0.090 Uiso 1 1 calc R . .
C3 C 0.66512(19) -0.03013(10) 1.38851(16) 0.0776(4) Uani 1 1 d . . .
H3 H 0.6582 -0.0474 1.4763 0.093 Uiso 1 1 calc R . .
C4 C 0.75036(18) -0.06909(9) 1.31978(17) 0.0725(4) Uani 1 1 d . . .
H4 H 0.8000 -0.1133 1.3599 0.087 Uiso 1 1 calc R . .
C5 C 0.76264(15) -0.04286(7) 1.19115(14) 0.0593(3) Uani 1 1 d . . .
H5 H 0.8210 -0.0693 1.1446 0.071 Uiso 1 1 calc R . .
C6 C 0.68857(13) 0.02252(6) 1.13096(12) 0.0468(3) Uani 1 1 d . . .
C7 C 0.68411(13) 0.13133(6) 0.82547(12) 0.0465(3) Uani 1 1 d . . .
C8 C 0.80239(15) 0.10127(8) 0.78070(14) 0.0621(3) Uani 1 1 d . . .
H8 H 0.8616 0.0619 0.8322 0.074 Uiso 1 1 calc R . .
C9 C 0.83195(17) 0.12946(9) 0.66121(16) 0.0710(4) Uani 1 1 d . . .
H9 H 0.9099 0.1085 0.6311 0.085 Uiso 1 1 calc R . .
C10 C 0.74642(16) 0.18880(9) 0.58556(14) 0.0665(4) Uani 1 1 d . . .
H10 H 0.7683 0.2082 0.5057 0.080 Uiso 1 1 calc R . .
C11 C 0.62934(15) 0.21940(7) 0.62737(13) 0.0544(3) Uani 1 1 d . . .
H11 H 0.5718 0.2592 0.5755 0.065 Uiso 1 1 calc R . .
C12 C 0.59661(13) 0.19088(6) 0.74751(11) 0.0445(3) Uani 1 1 d . . .
C13 C 0.27381(13) 0.29645(6) 0.76577(12) 0.0471(3) Uani 1 1 d . . .
C14 C 0.21517(15) 0.25803(7) 0.86029(14) 0.0557(3) Uani 1 1 d . . .
H14 H 0.2648 0.2153 0.9075 0.067 Uiso 1 1 calc R . .
C15 C 0.08271(17) 0.28353(8) 0.88398(17) 0.0681(4) Uani 1 1 d . . .
H15 H 0.0428 0.2577 0.9470 0.082 Uiso 1 1 calc R . .
C16 C 0.00916(16) 0.34700(9) 0.81486(17) 0.0699(4) Uani 1 1 d . . .
H16 H -0.0806 0.3637 0.8306 0.084 Uiso 1 1 calc R . .
C17 C 0.06846(16) 0.38568(8) 0.72266(17) 0.0701(4) Uani 1 1 d . . .
H17 H 0.0192 0.4288 0.6766 0.084 Uiso 1 1 calc R . .
C18 C 0.20094(15) 0.36081(8) 0.69809(15) 0.0615(3) Uani 1 1 d . . .
H18 H 0.2413 0.3873 0.6361 0.074 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
N1 N2 1.2436(13) . ?
N1 C6 1.4240(15) . ?
N2 C7 1.4259(15) . ?
N3 N4 1.2426(13) . ?
N3 C12 1.4270(14) . ?
N4 C13 1.4259(15) . ?
C1 C2 1.3740(19) . ?
C1 C6 1.3851(17) . ?
C1 H1 0.9300 . ?
C2 C3 1.380(2) . ?
C2 H2 0.9300 . ?
C3 C4 1.367(2) . ?
C3 H3 0.9300 . ?
C4 C5 1.3758(19) . ?
C4 H4 0.9300 . ?
C5 C6 1.3808(16) . ?
C5 H5 0.9300 . ?
C7 C8 1.3942(16) . ?
C7 C12 1.3988(16) . ?
C8 C9 1.3717(19) . ?
C8 H8 0.9300 . ?
C9 C10 1.3807(19) . ?
C9 H9 0.9300 . ?
C10 C11 1.3724(17) . ?
C10 H10 0.9300 . ?
C11 C12 1.3934(16) . ?
C11 H11 0.9300 . ?
C13 C18 1.3834(16) . ?
C13 C14 1.3847(17) . ?
C14 C15 1.3788(18) . ?
C14 H14 0.9300 . ?
C15 C16 1.377(2) . ?
C15 H15 0.9300 . ?
C16 C17 1.373(2) . ?
C16 H16 0.9300 . ?
C17 C18 1.3792(19) . ?
C17 H17 0.9300 . ?
C18 H18 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
N2 N1 C6 114.30(9) . . ?
N1 N2 C7 113.79(9) . . ?
N4 N3 C12 114.16(9) . . ?
N3 N4 C13 114.49(10) . . ?
C2 C1 C6 119.15(13) . . ?
C2 C1 H1 120.4 . . ?
C6 C1 H1 120.4 . . ?
C1 C2 C3 120.62(14) . . ?
C1 C2 H2 119.7 . . ?
C3 C2 H2 119.7 . . ?
C4 C3 C2 120.10(14) . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
C3 C4 C5 119.90(14) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
C4 C5 C6 120.21(13) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 H5 119.9 . . ?
C5 C6 C1 120.00(11) . . ?
C5 C6 N1 115.46(11) . . ?
C1 C6 N1 124.53(11) . . ?
C8 C7 C12 119.16(11) . . ?
C8 C7 N2 123.16(10) . . ?
C12 C7 N2 117.62(9) . . ?
C9 C8 C7 120.40(12) . . ?
C9 C8 H8 119.8 . . ?
C7 C8 H8 119.8 . . ?
C8 C9 C10 120.23(12) . . ?
C8 C9 H9 119.9 . . ?
C10 C9 H9 119.9 . . ?
C11 C10 C9 120.51(12) . . ?
C11 C10 H10 119.7 . . ?
C9 C10 H10 119.7 . . ?
C10 C11 C12 120.01(12) . . ?
C10 C11 H11 120.0 . . ?
C12 C11 H11 120.0 . . ?
C11 C12 C7 119.68(10) . . ?
C11 C12 N3 123.39(10) . . ?
C7 C12 N3 116.83(10) . . ?
C18 C13 C14 119.84(11) . . ?
C18 C13 N4 115.69(11) . . ?
C14 C13 N4 124.45(10) . . ?
C15 C14 C13 119.60(12) . . ?
C15 C14 H14 120.2 . . ?
C13 C14 H14 120.2 . . ?
C16 C15 C14 120.43(13) . . ?
C16 C15 H15 119.8 . . ?
C14 C15 H15 119.8 . . ?
C17 C16 C15 119.97(13) . . ?
C17 C16 H16 120.0 . . ?
C15 C16 H16 120.0 . . ?
C16 C17 C18 120.18(13) . . ?
C16 C17 H17 119.9 . . ?
C18 C17 H17 119.9 . . ?
C17 C18 C13 119.96(13) . . ?
C17 C18 H18 120.0 . . ?
C13 C18 H18 120.0 . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.173
_refine_diff_density_min         -0.137
_refine_diff_density_rms         0.033


####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1031476'
_audit_update_record             
;
2014-10-29 deposited with the CCDC.
2015-02-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C20 H16 N4 O2 Pd), H2 O'
_chemical_formula_sum            'C40 H34 N8 O5 Pd2'
_chemical_formula_weight         919.55

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'
Pd Pd -0.9988 1.0072 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           MOnoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   P2(1)/n
_symmetry_Int_Tables_number      14

loop_
_symmetry_equiv_pos_as_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                   11.2390(5)
_cell_length_b                   22.3058(10)
_cell_length_c                   15.2021(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 104.171(2)
_cell_angle_gamma                90.00
_cell_volume                     3695.1(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1476
_cell_measurement_theta_min      1.66
_cell_measurement_theta_max      27.51

_exptl_crystal_description       parallelopiped
_exptl_crystal_colour            Red
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.21
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.653
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1848
_exptl_absorpt_coefficient_mu    1.031
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.656
_exptl_absorpt_correction_T_max  0.805
_exptl_absorpt_process_details   'Sadabs(Sheldrick, 1996)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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  'CCD area-detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            61448
_diffrn_reflns_av_R_equivalents  0.0351
_diffrn_reflns_av_sigmaI/netI    0.0233
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.66
_diffrn_reflns_theta_max         27.51
_reflns_number_total             8482
_reflns_number_gt                6431
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'SMART APEX II (Bruker,2010)'
_computing_cell_refinement       'SMART APEX II'
_computing_data_reduction        'SAINT (Bruker,2000)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Ortep-3v2 for windows (Farrugia, 1997)'
_computing_publication_material  'PLATON (Spek, 2008)'

_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 > 2sigma(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)+(0.0348P)²+1.2732P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         8482
_refine_ls_number_parameters     506
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0428
_refine_ls_R_factor_gt           0.0278
_refine_ls_wR_factor_ref         0.0745
_refine_ls_wR_factor_gt          0.0666
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_restrained_S_all      1.015
_refine_ls_shift/su_max          0.004
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Pd1 Pd 0.234478(17) 0.669473(7) 0.193111(12) 0.03961(6) Uani 1 1 d . . .
N1 N 0.28684(18) 0.78908(8) 0.15186(14) 0.0459(5) Uani 1 1 d . . .
N2 N 0.25907(17) 0.75532(8) 0.21141(13) 0.0410(4) Uani 1 1 d . . .
N3 N 0.19341(18) 0.67787(8) 0.32564(13) 0.0420(4) Uani 1 1 d . . .
N4 N 0.16334(19) 0.64534(9) 0.38430(14) 0.0496(5) Uani 1 1 d . . .
O1 O 0.20307(18) 0.58132(7) 0.15577(13) 0.0538(4) Uani 1 1 d . . .
O2 O 0.0095(2) 0.59540(9) 0.15447(16) 0.0779(6) Uani 1 1 d . . .
C1 C 0.2827(2) 0.69195(11) 0.08111(16) 0.0429(5) Uani 1 1 d . . .
C2 C 0.2982(2) 0.65807(12) 0.00894(17) 0.0521(6) Uani 1 1 d . . .
H2A H 0.2849 0.6169 0.0076 0.062 Uiso 1 1 calc R . .
C3 C 0.3341(3) 0.68630(14) -0.06175(19) 0.0601(7) Uani 1 1 d . . .
H3A H 0.3466 0.6631 -0.1095 0.072 Uiso 1 1 calc R . .
C4 C 0.3518(3) 0.74708(14) -0.06395(19) 0.0625(8) Uani 1 1 d . . .
H4A H 0.3743 0.7645 -0.1131 0.075 Uiso 1 1 calc R . .
C5 C 0.3363(2) 0.78189(13) 0.00663(19) 0.0561(7) Uani 1 1 d . . .
H5A H 0.3474 0.8232 0.0060 0.067 Uiso 1 1 calc R . .
C6 C 0.3034(2) 0.75409(10) 0.07951(16) 0.0433(5) Uani 1 1 d . . .
C7 C 0.2284(2) 0.78106(10) 0.28761(16) 0.0424(5) Uani 1 1 d . . .
C8 C 0.2326(3) 0.84220(11) 0.30556(19) 0.0566(7) Uani 1 1 d . . .
H8A H 0.2592 0.8689 0.2674 0.068 Uiso 1 1 calc R . .
C9 C 0.1971(3) 0.86265(13) 0.3799(2) 0.0663(8) Uani 1 1 d . . .
H9A H 0.2012 0.9034 0.3932 0.080 Uiso 1 1 calc R . .
C10 C 0.1550(3) 0.82303(13) 0.4357(2) 0.0678(8) Uani 1 1 d . . .
H10A H 0.1288 0.8377 0.4850 0.081 Uiso 1 1 calc R . .
C11 C 0.1514(3) 0.76284(13) 0.41922(18) 0.0574(7) Uani 1 1 d . . .
H11A H 0.1233 0.7367 0.4573 0.069 Uiso 1 1 calc R . .
C12 C 0.1900(2) 0.74085(10) 0.34526(16) 0.0428(5) Uani 1 1 d . . .
C13 C 0.1775(2) 0.58265(11) 0.37699(16) 0.0481(6) Uani 1 1 d . . .
C14 C 0.0888(3) 0.54708(13) 0.40210(17) 0.0588(7) Uani 1 1 d . . .
H14A H 0.0210 0.5644 0.4169 0.071 Uiso 1 1 calc R . .
C15 C 0.1042(3) 0.48595(14) 0.4044(2) 0.0699(9) Uani 1 1 d . . .
H15A H 0.0443 0.4615 0.4184 0.084 Uiso 1 1 calc R . .
C16 C 0.2067(4) 0.46040(13) 0.3864(2) 0.0729(9) Uani 1 1 d . . .
H16A H 0.2169 0.4190 0.3895 0.087 Uiso 1 1 calc R . .
C17 C 0.2947(3) 0.49620(12) 0.3635(2) 0.0670(8) Uani 1 1 d . . .
H17A H 0.3643 0.4789 0.3515 0.080 Uiso 1 1 calc R . .
C18 C 0.2800(3) 0.55739(11) 0.35845(17) 0.0533(6) Uani 1 1 d . . .
H18A H 0.3390 0.5815 0.3426 0.064 Uiso 1 1 calc R . .
C19 C 0.0959(3) 0.56413(11) 0.14687(17) 0.0535(6) Uani 1 1 d . . .
C20 C 0.0754(4) 0.49772(13) 0.1272(3) 0.0901(11) Uani 1 1 d . . .
H20A H 0.1056 0.4753 0.1820 0.135 Uiso 1 1 calc R . .
H20B H 0.1184 0.4857 0.0828 0.135 Uiso 1 1 calc R . .
H20C H -0.0107 0.4902 0.1044 0.135 Uiso 1 1 calc R . .
Pd2 Pd 0.052890(16) 0.830712(7) -0.140264(12) 0.03922(6) Uani 1 1 d . . .
N5 N 0.00604(18) 0.71708(9) -0.07245(15) 0.0493(5) Uani 1 1 d . . .
N6 N 0.03287(17) 0.74425(8) -0.13924(13) 0.0425(5) Uani 1 1 d . . .
N7 N 0.09612(17) 0.80855(9) -0.26910(13) 0.0434(5) Uani 1 1 d . . .
N8 N 0.1266(2) 0.83491(9) -0.33326(15) 0.0525(5) Uani 1 1 d . . .
O3 O 0.07726(17) 0.92099(7) -0.12495(12) 0.0506(4) Uani 1 1 d . . .
O4 O 0.27237(18) 0.90617(8) -0.12241(14) 0.0644(5) Uani 1 1 d . . .
C21 C 0.0075(2) 0.82006(10) -0.02431(16) 0.0431(5) Uani 1 1 d . . .
C22 C -0.0073(2) 0.86071(12) 0.04121(18) 0.0525(6) Uani 1 1 d . . .
H22A H 0.0032 0.9015 0.0330 0.063 Uiso 1 1 calc R . .
C23 C -0.0378(3) 0.84039(14) 0.1186(2) 0.0645(8) Uani 1 1 d . . .
H23A H -0.0474 0.8681 0.1621 0.077 Uiso 1 1 calc R . .
C24 C -0.0546(2) 0.78004(14) 0.13351(19) 0.0625(8) Uani 1 1 d . . .
H24A H -0.0748 0.7677 0.1865 0.075 Uiso 1 1 calc R . .
C25 C -0.0416(2) 0.73867(13) 0.07045(19) 0.0561(7) Uani 1 1 d . . .
H25A H -0.0528 0.6981 0.0797 0.067 Uiso 1 1 calc R . .
C26 C -0.0111(2) 0.75870(11) -0.00844(17) 0.0457(6) Uani 1 1 d . . .
C27 C 0.0657(2) 0.71057(10) -0.20772(17) 0.0456(6) Uani 1 1 d . . .
C28 C 0.0669(3) 0.64840(11) -0.2090(2) 0.0591(7) Uani 1 1 d . . .
H28A H 0.0411 0.6264 -0.1651 0.071 Uiso 1 1 calc R . .
C29 C 0.1068(3) 0.61996(13) -0.2764(2) 0.0701(9) Uani 1 1 d . . .
H29A H 0.1080 0.5783 -0.2781 0.084 Uiso 1 1 calc R . .
C30 C 0.1454(3) 0.65237(14) -0.3418(2) 0.0735(9) Uani 1 1 d . . .
H30A H 0.1725 0.6323 -0.3869 0.088 Uiso 1 1 calc R . .
C31 C 0.1441(3) 0.71391(13) -0.3410(2) 0.0617(7) Uani 1 1 d . . .
H31A H 0.1705 0.7353 -0.3852 0.074 Uiso 1 1 calc R . .
C32 C 0.1034(2) 0.74411(11) -0.27416(16) 0.0458(6) Uani 1 1 d . . .
C33 C 0.1082(2) 0.89787(11) -0.34088(16) 0.0485(6) Uani 1 1 d . . .
C34 C 0.1941(3) 0.93026(13) -0.37403(19) 0.0657(8) Uani 1 1 d . . .
H34A H 0.2632 0.9116 -0.3846 0.079 Uiso 1 1 calc R . .
C35 C 0.1739(3) 0.99061(15) -0.3907(2) 0.0799(10) Uani 1 1 d . . .
H35A H 0.2322 1.0134 -0.4097 0.096 Uiso 1 1 calc R . .
C36 C 0.0695(4) 1.01722(14) -0.3795(2) 0.0830(10) Uani 1 1 d . . .
H36A H 0.0557 1.0577 -0.3928 0.100 Uiso 1 1 calc R . .
C37 C -0.0151(3) 0.98447(13) -0.3486(2) 0.0719(8) Uani 1 1 d . . .
H37A H -0.0864 1.0028 -0.3413 0.086 Uiso 1 1 calc R . .
C38 C 0.0044(3) 0.92489(11) -0.32839(17) 0.0543(6) Uani 1 1 d . . .
H38A H -0.0526 0.9030 -0.3064 0.065 Uiso 1 1 calc R . .
C39 C 0.1845(3) 0.93904(10) -0.12265(15) 0.0470(6) Uani 1 1 d . . .
C40 C 0.1983(3) 1.00636(11) -0.1214(2) 0.0718(9) Uani 1 1 d . . .
H40A H 0.2836 1.0166 -0.1113 0.108 Uiso 1 1 calc R . .
H40B H 0.1663 1.0228 -0.0736 0.108 Uiso 1 1 calc R . .
H40C H 0.1539 1.0225 -0.1785 0.108 Uiso 1 1 calc R . .
O1S O 0.3974(2) 0.83505(11) -0.22902(18) 0.0824(7) Uani 1 1 d D . .
H1SA H 0.354(5) 0.8609(17) -0.213(4) 0.28(4) Uiso 1 1 d D . .
H1SB H 0.430(3) 0.8568(14) -0.261(2) 0.110(15) Uiso 1 1 d D . .


_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 N2 1.9450(18) . ?
Pd1 C1 1.974(2) . ?
Pd1 O1 2.0532(16) . ?
Pd1 N3 2.1823(19) . ?
N1 N2 1.274(2) . ?
N1 C6 1.398(3) . ?
N2 C7 1.409(3) . ?
N3 N4 1.258(3) . ?
N3 C12 1.439(3) . ?
N4 C13 1.415(3) . ?
O1 C19 1.239(3) . ?
O2 C19 1.224(3) . ?
C1 C2 1.378(3) . ?
C1 C6 1.407(3) . ?
C2 C3 1.388(4) . ?
C2 H2A 0.9300 . ?
C3 C4 1.372(4) . ?
C3 H3A 0.9300 . ?
C4 C5 1.370(4) . ?
C4 H4A 0.9300 . ?
C5 C6 1.396(3) . ?
C5 H5A 0.9300 . ?
C7 C8 1.389(3) . ?
C7 C12 1.394(3) . ?
C8 C9 1.366(4) . ?
C8 H8A 0.9300 . ?
C9 C10 1.385(4) . ?
C9 H9A 0.9300 . ?
C10 C11 1.365(4) . ?
C10 H10A 0.9300 . ?
C11 C12 1.390(3) . ?
C11 H11A 0.9300 . ?
C13 C18 1.373(3) . ?
C13 C14 1.398(3) . ?
C14 C15 1.374(4) . ?
C14 H14A 0.9300 . ?
C15 C16 1.372(4) . ?
C15 H15A 0.9300 . ?
C16 C17 1.380(4) . ?
C16 H16A 0.9300 . ?
C17 C18 1.375(4) . ?
C17 H17A 0.9300 . ?
C18 H18A 0.9300 . ?
C19 C20 1.518(4) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
Pd2 N6 1.9423(18) . ?
Pd2 C21 1.966(2) . ?
Pd2 O3 2.0380(16) . ?
Pd2 N7 2.1868(19) . ?
N5 N6 1.280(3) . ?
N5 C26 1.392(3) . ?
N6 C27 1.404(3) . ?
N7 N8 1.256(3) . ?
N7 C32 1.443(3) . ?
N8 C33 1.420(3) . ?
O3 C39 1.263(3) . ?
O4 C39 1.229(3) . ?
C21 C22 1.387(3) . ?
C21 C26 1.414(3) . ?
C22 C23 1.379(4) . ?
C22 H22A 0.9300 . ?
C23 C24 1.386(4) . ?
C23 H23A 0.9300 . ?
C24 C25 1.364(4) . ?
C24 H24A 0.9300 . ?
C25 C26 1.399(3) . ?
C25 H25A 0.9300 . ?
C27 C28 1.387(3) . ?
C27 C32 1.403(3) . ?
C28 C29 1.370(4) . ?
C28 H28A 0.9300 . ?
C29 C30 1.382(4) . ?
C29 H29A 0.9300 . ?
C30 C31 1.373(4) . ?
C30 H30A 0.9300 . ?
C31 C32 1.386(3) . ?
C31 H31A 0.9300 . ?
C33 C38 1.368(4) . ?
C33 C34 1.394(3) . ?
C34 C35 1.378(4) . ?
C34 H34A 0.9300 . ?
C35 C36 1.362(5) . ?
C35 H35A 0.9300 . ?
C36 C37 1.371(4) . ?
C36 H36A 0.9300 . ?
C37 C38 1.369(4) . ?
C37 H37A 0.9300 . ?
C38 H38A 0.9300 . ?
C39 C40 1.509(3) . ?
C40 H40A 0.9600 . ?
C40 H40B 0.9600 . ?
C40 H40C 0.9600 . ?
O1S H1SA 0.833(10) . ?
O1S H1SB 0.833(10) . ?

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 C1 79.27(9) . . ?
N2 Pd1 O1 172.42(8) . . ?
C1 Pd1 O1 94.00(9) . . ?
N2 Pd1 N3 80.69(7) . . ?
C1 Pd1 N3 159.95(9) . . ?
O1 Pd1 N3 106.05(7) . . ?
N2 N1 C6 109.40(18) . . ?
N1 N2 C7 119.68(19) . . ?
N1 N2 Pd1 122.09(16) . . ?
C7 N2 Pd1 117.64(15) . . ?
N4 N3 C12 113.00(19) . . ?
N4 N3 Pd1 139.38(16) . . ?
C12 N3 Pd1 107.31(14) . . ?
N3 N4 C13 117.4(2) . . ?
C19 O1 Pd1 115.04(16) . . ?
C2 C1 C6 118.2(2) . . ?
C2 C1 Pd1 131.49(19) . . ?
C6 C1 Pd1 110.28(17) . . ?
C1 C2 C3 119.0(3) . . ?
C1 C2 H2A 120.5 . . ?
C3 C2 H2A 120.5 . . ?
C4 C3 C2 122.6(3) . . ?
C4 C3 H3A 118.7 . . ?
C2 C3 H3A 118.7 . . ?
C5 C4 C3 119.6(3) . . ?
C5 C4 H4A 120.2 . . ?
C3 C4 H4A 120.2 . . ?
C4 C5 C6 118.6(3) . . ?
C4 C5 H5A 120.7 . . ?
C6 C5 H5A 120.7 . . ?
C5 C6 N1 119.3(2) . . ?
C5 C6 C1 121.9(2) . . ?
N1 C6 C1 118.8(2) . . ?
C8 C7 C12 120.6(2) . . ?
C8 C7 N2 123.9(2) . . ?
C12 C7 N2 115.5(2) . . ?
C9 C8 C7 119.2(3) . . ?
C9 C8 H8A 120.4 . . ?
C7 C8 H8A 120.4 . . ?
C8 C9 C10 120.4(3) . . ?
C8 C9 H9A 119.8 . . ?
C10 C9 H9A 119.8 . . ?
C11 C10 C9 121.0(3) . . ?
C11 C10 H10A 119.5 . . ?
C9 C10 H10A 119.5 . . ?
C10 C11 C12 119.6(3) . . ?
C10 C11 H11A 120.2 . . ?
C12 C11 H11A 120.2 . . ?
C11 C12 C7 119.2(2) . . ?
C11 C12 N3 122.8(2) . . ?
C7 C12 N3 118.0(2) . . ?
C18 C13 C14 120.9(2) . . ?
C18 C13 N4 122.5(2) . . ?
C14 C13 N4 116.0(2) . . ?
C15 C14 C13 118.5(3) . . ?
C15 C14 H14A 120.8 . . ?
C13 C14 H14A 120.8 . . ?
C16 C15 C14 120.9(3) . . ?
C16 C15 H15A 119.6 . . ?
C14 C15 H15A 119.6 . . ?
C15 C16 C17 119.9(3) . . ?
C15 C16 H16A 120.0 . . ?
C17 C16 H16A 120.0 . . ?
C18 C17 C16 120.3(3) . . ?
C18 C17 H17A 119.8 . . ?
C16 C17 H17A 119.8 . . ?
C13 C18 C17 119.4(3) . . ?
C13 C18 H18A 120.3 . . ?
C17 C18 H18A 120.3 . . ?
O2 C19 O1 125.9(2) . . ?
O2 C19 C20 119.3(3) . . ?
O1 C19 C20 114.8(3) . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
N6 Pd2 C21 79.44(9) . . ?
N6 Pd2 O3 173.17(8) . . ?
C21 Pd2 O3 94.25(8) . . ?
N6 Pd2 N7 80.46(8) . . ?
C21 Pd2 N7 159.90(9) . . ?
O3 Pd2 N7 105.82(7) . . ?
N6 N5 C26 109.79(19) . . ?
N5 N6 C27 119.4(2) . . ?
N5 N6 Pd2 121.78(16) . . ?
C27 N6 Pd2 118.25(15) . . ?
N8 N7 C32 113.28(19) . . ?
N8 N7 Pd2 138.78(16) . . ?
C32 N7 Pd2 107.51(14) . . ?
N7 N8 C33 117.7(2) . . ?
C39 O3 Pd2 114.76(15) . . ?
C22 C21 C26 117.5(2) . . ?
C22 C21 Pd2 131.93(19) . . ?
C26 C21 Pd2 110.60(17) . . ?
C23 C22 C21 119.7(3) . . ?
C23 C22 H22A 120.1 . . ?
C21 C22 H22A 120.1 . . ?
C22 C23 C24 122.1(3) . . ?
C22 C23 H23A 118.9 . . ?
C24 C23 H23A 118.9 . . ?
C25 C24 C23 120.0(3) . . ?
C25 C24 H24A 120.0 . . ?
C23 C24 H24A 120.0 . . ?
C24 C25 C26 118.5(3) . . ?
C24 C25 H25A 120.7 . . ?
C26 C25 H25A 120.7 . . ?
N5 C26 C25 119.4(2) . . ?
N5 C26 C21 118.3(2) . . ?
C25 C26 C21 122.2(2) . . ?
C28 C27 C32 121.1(2) . . ?
C28 C27 N6 123.4(2) . . ?
C32 C27 N6 115.4(2) . . ?
C29 C28 C27 118.7(3) . . ?
C29 C28 H28A 120.7 . . ?
C27 C28 H28A 120.7 . . ?
C28 C29 C30 120.9(3) . . ?
C28 C29 H29A 119.6 . . ?
C30 C29 H29A 119.6 . . ?
C31 C30 C29 120.7(3) . . ?
C31 C30 H30A 119.7 . . ?
C29 C30 H30A 119.7 . . ?
C30 C31 C32 119.9(3) . . ?
C30 C31 H31A 120.0 . . ?
C32 C31 H31A 120.0 . . ?
C31 C32 C27 118.7(2) . . ?
C31 C32 N7 123.8(2) . . ?
C27 C32 N7 117.5(2) . . ?
C38 C33 C34 120.7(2) . . ?
C38 C33 N8 122.4(2) . . ?
C34 C33 N8 116.3(2) . . ?
C35 C34 C33 118.4(3) . . ?
C35 C34 H34A 120.8 . . ?
C33 C34 H34A 120.8 . . ?
C36 C35 C34 120.7(3) . . ?
C36 C35 H35A 119.6 . . ?
C34 C35 H35A 119.6 . . ?
C35 C36 C37 120.1(3) . . ?
C35 C36 H36A 119.9 . . ?
C37 C36 H36A 119.9 . . ?
C38 C37 C36 120.5(3) . . ?
C38 C37 H37A 119.8 . . ?
C36 C37 H37A 119.8 . . ?
C33 C38 C37 119.5(3) . . ?
C33 C38 H38A 120.3 . . ?
C37 C38 H38A 120.3 . . ?
O4 C39 O3 124.8(2) . . ?
O4 C39 C40 120.9(3) . . ?
O3 C39 C40 114.3(2) . . ?
C39 C40 H40A 109.5 . . ?
C39 C40 H40B 109.5 . . ?
H40A C40 H40B 109.5 . . ?
C39 C40 H40C 109.5 . . ?
H40A C40 H40C 109.5 . . ?
H40B C40 H40C 109.5 . . ?
H1SA O1S H1SB 98(2) . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        27.51
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.574
_refine_diff_density_min         -0.410
_refine_diff_density_rms         0.059

####################################################################### 
# 
# 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_2
_database_code_depnum_ccdc_archive 'CCDC 1031477'
_audit_update_record             
;
2014-10-29 deposited with the CCDC.
2015-02-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H13 Cl N4 Pd'
_chemical_formula_sum            'C18 H13 Cl N4 Pd'
_chemical_formula_weight         427.17

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'
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'

_symmetry_cell_setting           MOnoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   C2/c
_symmetry_Int_Tables_number      15

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

_cell_length_a                   21.9347(6)
_cell_length_b                   6.9520(2)
_cell_length_c                   23.1894(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 112.175(3)
_cell_angle_gamma                90.00
_cell_volume                     3274.60(16)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1052
_cell_measurement_theta_min      2.01
_cell_measurement_theta_max      27.57

_exptl_crystal_description       parallelopiped
_exptl_crystal_colour            Red
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.16
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.733
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1696
_exptl_absorpt_coefficient_mu    1.303
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.615
_exptl_absorpt_correction_T_max  0.812
_exptl_absorpt_process_details   'Sadabs(Sheldrick, 1996)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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  'CCD area-detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            26677
_diffrn_reflns_av_R_equivalents  0.0386
_diffrn_reflns_av_sigmaI/netI    0.0235
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         2.01
_diffrn_reflns_theta_max         27.57
_reflns_number_total             3758
_reflns_number_gt                3150
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'SMART APEX II (Bruker,2010)'
_computing_cell_refinement       'SMART APEX II'
_computing_data_reduction        'SAINT (Bruker,2000)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Ortep-3v2 for windows (Farrugia, 1997)'
_computing_publication_material  'PLATON (Spek, 2008)'

_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 > 2sigma(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)+(0.0297P)²+3.6255P] 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         3758
_refine_ls_number_parameters     217
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0353
_refine_ls_R_factor_gt           0.0270
_refine_ls_wR_factor_ref         0.0675
_refine_ls_wR_factor_gt          0.0626
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_restrained_S_all      1.025
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Pd1 Pd 0.080183(9) 0.71365(3) 0.044196(8) 0.04068(7) Uani 1 1 d . . .
Cl1 Cl 0.18957(4) 0.69465(14) 0.10630(4) 0.0706(2) Uani 1 1 d . . .
N1 N -0.02185(11) 0.7393(3) -0.07579(10) 0.0477(5) Uani 1 1 d . . .
N2 N -0.00972(10) 0.7454(3) -0.01725(10) 0.0413(5) Uani 1 1 d . . .
N3 N 0.02486(12) 0.7641(3) 0.10604(11) 0.0496(5) Uani 1 1 d . . .
N4 N 0.03754(14) 0.8086(4) 0.16122(12) 0.0650(7) Uani 1 1 d . . .
C1 C 0.09560(13) 0.6868(3) -0.03383(12) 0.0446(6) Uani 1 1 d . . .
C2 C 0.15259(14) 0.6561(4) -0.04526(14) 0.0539(6) Uani 1 1 d . . .
H2A H 0.1930 0.6449 -0.0122 0.065 Uiso 1 1 calc R . .
C3 C 0.14919(16) 0.6423(5) -0.10605(15) 0.0629(8) Uani 1 1 d . . .
H3A H 0.1876 0.6214 -0.1132 0.075 Uiso 1 1 calc R . .
C4 C 0.09048(17) 0.6587(5) -0.15606(15) 0.0665(8) Uani 1 1 d . . .
H4A H 0.0896 0.6479 -0.1963 0.080 Uiso 1 1 calc R . .
C5 C 0.03330(16) 0.6908(4) -0.14671(14) 0.0610(8) Uani 1 1 d . . .
H5A H -0.0066 0.7028 -0.1803 0.073 Uiso 1 1 calc R . .
C6 C 0.03622(13) 0.7050(4) -0.08532(12) 0.0460(6) Uani 1 1 d . . .
C7 C -0.06145(12) 0.7840(3) 0.00278(13) 0.0438(5) Uani 1 1 d . . .
C8 C -0.12583(13) 0.8111(4) -0.03731(14) 0.0521(6) Uani 1 1 d . . .
H8A H -0.1372 0.8035 -0.0802 0.063 Uiso 1 1 calc R . .
C9 C -0.17318(14) 0.8496(4) -0.01320(16) 0.0606(7) Uani 1 1 d . . .
H9A H -0.2167 0.8680 -0.0399 0.073 Uiso 1 1 calc R . .
C10 C -0.15625(14) 0.8610(4) 0.05023(16) 0.0605(7) Uani 1 1 d . . .
H10A H -0.1886 0.8876 0.0659 0.073 Uiso 1 1 calc R . .
C11 C -0.09256(14) 0.8338(4) 0.09063(15) 0.0545(7) Uani 1 1 d . . .
H11A H -0.0820 0.8398 0.1334 0.065 Uiso 1 1 calc R . .
C12 C -0.04391(12) 0.7973(3) 0.06737(13) 0.0455(6) Uani 1 1 d . . .
C13 C 0.10088(16) 0.7540(5) 0.20470(14) 0.0649(8) Uani 1 1 d . . .
C14 C 0.12888(15) 0.5741(5) 0.20481(13) 0.0652(8) Uani 1 1 d . . .
H14A H 0.1091 0.4877 0.1725 0.078 Uiso 1 1 calc R . .
C15 C 0.18641(16) 0.5259(7) 0.25356(15) 0.0850(12) Uani 1 1 d . . .
H15A H 0.2050 0.4047 0.2552 0.102 Uiso 1 1 calc R . .
C16 C 0.2157(2) 0.6569(10) 0.29913(18) 0.115(2) Uani 1 1 d . . .
H16A H 0.2549 0.6241 0.3314 0.138 Uiso 1 1 calc R . .
C17 C 0.1899(3) 0.8326(9) 0.29922(19) 0.1157(19) Uani 1 1 d . . .
H17A H 0.2119 0.9200 0.3305 0.139 Uiso 1 1 calc R . .
C18 C 0.1307(2) 0.8831(6) 0.25269(17) 0.0925(12) Uani 1 1 d . . .
H18A H 0.1113 1.0014 0.2536 0.111 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 N2 1.961(2) . ?
Pd1 C1 1.971(3) . ?
Pd1 N3 2.229(2) . ?
Pd1 Cl1 2.2892(7) . ?
N1 N2 1.282(3) . ?
N1 C6 1.393(4) . ?
N2 C7 1.405(3) . ?
N3 N4 1.242(3) . ?
N3 C12 1.453(3) . ?
N4 C13 1.426(4) . ?
C1 C2 1.389(4) . ?
C1 C6 1.402(4) . ?
C2 C3 1.387(4) . ?
C2 H2A 0.9300 . ?
C3 C4 1.374(4) . ?
C3 H3A 0.9300 . ?
C4 C5 1.369(4) . ?
C4 H4A 0.9300 . ?
C5 C6 1.404(4) . ?
C5 H5A 0.9300 . ?
C7 C8 1.379(4) . ?
C7 C12 1.402(4) . ?
C8 C9 1.379(4) . ?
C8 H8A 0.9300 . ?
C9 C10 1.377(4) . ?
C9 H9A 0.9300 . ?
C10 C11 1.370(4) . ?
C10 H10A 0.9300 . ?
C11 C12 1.389(4) . ?
C11 H11A 0.9300 . ?
C13 C18 1.386(5) . ?
C13 C14 1.393(5) . ?
C14 C15 1.381(4) . ?
C14 H14A 0.9300 . ?
C15 C16 1.359(6) . ?
C15 H15A 0.9300 . ?
C16 C17 1.346(7) . ?
C16 H16A 0.9300 . ?
C17 C18 1.385(6) . ?
C17 H17A 0.9300 . ?
C18 H18A 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
N2 Pd1 C1 79.49(10) . . ?
N2 Pd1 N3 78.90(9) . . ?
C1 Pd1 N3 158.35(10) . . ?
N2 Pd1 Cl1 172.42(6) . . ?
C1 Pd1 Cl1 94.00(8) . . ?
N3 Pd1 Cl1 107.48(6) . . ?
N2 N1 C6 109.7(2) . . ?
N1 N2 C7 119.1(2) . . ?
N1 N2 Pd1 121.04(18) . . ?
C7 N2 Pd1 119.83(17) . . ?
N4 N3 C12 111.9(2) . . ?
N4 N3 Pd1 137.5(2) . . ?
C12 N3 Pd1 108.56(16) . . ?
N3 N4 C13 116.2(3) . . ?
C2 C1 C6 117.7(2) . . ?
C2 C1 Pd1 131.9(2) . . ?
C6 C1 Pd1 110.31(19) . . ?
C3 C2 C1 119.9(3) . . ?
C3 C2 H2A 120.1 . . ?
C1 C2 H2A 120.1 . . ?
C4 C3 C2 121.7(3) . . ?
C4 C3 H3A 119.1 . . ?
C2 C3 H3A 119.1 . . ?
C5 C4 C3 120.2(3) . . ?
C5 C4 H4A 119.9 . . ?
C3 C4 H4A 119.9 . . ?
C4 C5 C6 118.6(3) . . ?
C4 C5 H5A 120.7 . . ?
C6 C5 H5A 120.7 . . ?
N1 C6 C1 119.5(2) . . ?
N1 C6 C5 118.6(2) . . ?
C1 C6 C5 122.0(3) . . ?
C8 C7 C12 120.6(2) . . ?
C8 C7 N2 123.5(2) . . ?
C12 C7 N2 115.8(2) . . ?
C9 C8 C7 119.3(3) . . ?
C9 C8 H8A 120.4 . . ?
C7 C8 H8A 120.4 . . ?
C10 C9 C8 120.2(3) . . ?
C10 C9 H9A 119.9 . . ?
C8 C9 H9A 119.9 . . ?
C11 C10 C9 121.1(3) . . ?
C11 C10 H10A 119.4 . . ?
C9 C10 H10A 119.4 . . ?
C10 C11 C12 119.6(3) . . ?
C10 C11 H11A 120.2 . . ?
C12 C11 H11A 120.2 . . ?
C11 C12 C7 119.1(2) . . ?
C11 C12 N3 124.1(2) . . ?
C7 C12 N3 116.8(2) . . ?
C18 C13 C14 120.4(3) . . ?
C18 C13 N4 115.7(3) . . ?
C14 C13 N4 123.5(3) . . ?
C15 C14 C13 119.1(3) . . ?
C15 C14 H14A 120.5 . . ?
C13 C14 H14A 120.5 . . ?
C16 C15 C14 119.4(5) . . ?
C16 C15 H15A 120.3 . . ?
C14 C15 H15A 120.3 . . ?
C17 C16 C15 122.3(4) . . ?
C17 C16 H16A 118.9 . . ?
C15 C16 H16A 118.9 . . ?
C16 C17 C18 120.0(4) . . ?
C16 C17 H17A 120.0 . . ?
C18 C17 H17A 120.0 . . ?
C17 C18 C13 118.8(4) . . ?
C17 C18 H18A 120.6 . . ?
C13 C18 H18A 120.6 . . ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        27.57
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.647
_refine_diff_density_min         -0.393
_refine_diff_density_rms         0.067

####################################################################### 
# 
# 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_3
_database_code_depnum_ccdc_archive 'CCDC 1031478'
_audit_update_record             
;
2014-10-29 deposited with the CCDC.
2015-02-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H13 Br N4 Pd'
_chemical_formula_sum            'C18 H13 Br N4 Pd'
_chemical_formula_weight         471.63

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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Pd Pd -0.9988 1.0072 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   P2(1)/n
_symmetry_Int_Tables_number      14

loop_
_symmetry_equiv_pos_as_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                   12.7588(3)
_cell_length_b                   6.8712(2)
_cell_length_c                   19.0666(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 93.2570(10)
_cell_angle_gamma                90.00
_cell_volume                     1668.84(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1147
_cell_measurement_theta_min      1.97
_cell_measurement_theta_max      28.16

_exptl_crystal_description       parallelopiped
_exptl_crystal_colour            Red
_exptl_crystal_size_max          0.52
_exptl_crystal_size_mid          0.43
_exptl_crystal_size_min          0.23
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.877
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             920
_exptl_absorpt_coefficient_mu    3.512
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.178
_exptl_absorpt_correction_T_max  0.445
_exptl_absorpt_process_details   'Sadabs(Sheldrick, 1996)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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  'CCD area-detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            27890
_diffrn_reflns_av_R_equivalents  0.0325
_diffrn_reflns_av_sigmaI/netI    0.0220
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         1.97
_diffrn_reflns_theta_max         28.16
_reflns_number_total             4072
_reflns_number_gt                3115
_reflns_threshold_expression     >2sigma(I)
_computing_data_collection       'SMART APEX II (Bruker,2010)'
_computing_cell_refinement       'SMART APEX II'
_computing_data_reduction        'SAINT (Bruker,2000)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Ortep-3v2 for windows (Farrugia, 1997)'
_computing_publication_material  'PLATON (Spek, 2008)'

_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 > 2sigma(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)+(0.0333P)²+0.9243P] 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         4072
_refine_ls_number_parameters     217
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0410
_refine_ls_R_factor_gt           0.0273
_refine_ls_wR_factor_ref         0.0719
_refine_ls_wR_factor_gt          0.0655
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_restrained_S_all      1.028
_refine_ls_shift/su_max          0.001
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Pd1 Pd 0.128294(15) 0.62686(3) 0.214645(10) 0.03738(7) Uani 1 1 d . . .
Br1 Br -0.05059(2) 0.61424(5) 0.166608(18) 0.06429(11) Uani 1 1 d . . .
N1 N 0.34800(18) 0.6156(3) 0.19702(13) 0.0461(5) Uani 1 1 d . . .
N2 N 0.27915(17) 0.6229(3) 0.24324(12) 0.0379(4) Uani 1 1 d . . .
N3 N 0.12375(18) 0.6191(3) 0.33120(12) 0.0436(5) Uani 1 1 d . . .
N4 N 0.0590(2) 0.5751(4) 0.37552(14) 0.0571(7) Uani 1 1 d . . .
C1 C 0.1891(2) 0.6151(4) 0.12156(14) 0.0423(6) Uani 1 1 d . . .
C2 C 0.1443(3) 0.6082(4) 0.05407(15) 0.0531(7) Uani 1 1 d . . .
H2A H 0.0717 0.6085 0.0466 0.064 Uiso 1 1 calc R . .
C3 C 0.2075(3) 0.6009(5) -0.00290(17) 0.0631(9) Uani 1 1 d . . .
H3A H 0.1762 0.5962 -0.0481 0.076 Uiso 1 1 calc R . .
C4 C 0.3152(3) 0.6005(5) 0.00610(17) 0.0646(9) Uani 1 1 d . . .
H4A H 0.3558 0.5973 -0.0329 0.078 Uiso 1 1 calc R . .
C5 C 0.3629(3) 0.6049(4) 0.07230(18) 0.0591(8) Uani 1 1 d . . .
H5A H 0.4357 0.6026 0.0788 0.071 Uiso 1 1 calc R . .
C6 C 0.2997(2) 0.6127(4) 0.12985(15) 0.0447(6) Uani 1 1 d . . .
C7 C 0.3111(2) 0.6207(4) 0.31457(14) 0.0402(6) Uani 1 1 d . . .
C8 C 0.4156(2) 0.6245(4) 0.33985(16) 0.0482(6) Uani 1 1 d . . .
H8A H 0.4693 0.6272 0.3088 0.058 Uiso 1 1 calc R . .
C9 C 0.4387(2) 0.6241(4) 0.41056(18) 0.0570(8) Uani 1 1 d . . .
H9A H 0.5084 0.6282 0.4277 0.068 Uiso 1 1 calc R . .
C10 C 0.3599(3) 0.6177(4) 0.45676(17) 0.0582(8) Uani 1 1 d . . .
H10A H 0.3770 0.6169 0.5048 0.070 Uiso 1 1 calc R . .
C11 C 0.2557(2) 0.6123(4) 0.43296(16) 0.0504(7) Uani 1 1 d . . .
H11A H 0.2031 0.6075 0.4647 0.061 Uiso 1 1 calc R . .
C12 C 0.2303(2) 0.6141(4) 0.36153(14) 0.0411(6) Uani 1 1 d . . .
C13 C -0.0483(2) 0.6069(5) 0.35527(17) 0.0568(8) Uani 1 1 d . . .
C14 C -0.0845(3) 0.7797(6) 0.32536(16) 0.0620(8) Uani 1 1 d . . .
H14A H -0.0376 0.8749 0.3123 0.074 Uiso 1 1 calc R . .
C15 C -0.1915(3) 0.8085(7) 0.31519(17) 0.0796(12) Uani 1 1 d . . .
H15A H -0.2173 0.9254 0.2966 0.096 Uiso 1 1 calc R . .
C16 C -0.2591(3) 0.6647(9) 0.3325(2) 0.0944(16) Uani 1 1 d . . .
H16A H -0.3309 0.6844 0.3245 0.113 Uiso 1 1 calc R . .
C17 C -0.2247(3) 0.4944(9) 0.3609(3) 0.0994(16) Uani 1 1 d . . .
H17A H -0.2723 0.3974 0.3711 0.119 Uiso 1 1 calc R . .
C18 C -0.1182(3) 0.4655(7) 0.3748(2) 0.0811(11) Uani 1 1 d . . .
H18A H -0.0939 0.3523 0.3970 0.097 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 N2 1.971(2) . ?
Pd1 C1 1.978(3) . ?
Pd1 N3 2.227(2) . ?
Pd1 Br1 2.4121(4) . ?
N1 N2 1.280(3) . ?
N1 C6 1.389(4) . ?
N2 C7 1.398(3) . ?
N3 N4 1.252(3) . ?
N3 C12 1.447(3) . ?
N4 C13 1.417(4) . ?
C1 C2 1.379(4) . ?
C1 C6 1.412(4) . ?
C2 C3 1.389(4) . ?
C2 H2A 0.9300 . ?
C3 C4 1.375(5) . ?
C3 H3A 0.9300 . ?
C4 C5 1.370(5) . ?
C4 H4A 0.9300 . ?
C5 C6 1.399(4) . ?
C5 H5A 0.9300 . ?
C7 C8 1.392(4) . ?
C7 C12 1.405(4) . ?
C8 C9 1.364(4) . ?
C8 H8A 0.9300 . ?
C9 C10 1.374(5) . ?
C9 H9A 0.9300 . ?
C10 C11 1.380(4) . ?
C10 H10A 0.9300 . ?
C11 C12 1.382(4) . ?
C11 H11A 0.9300 . ?
C13 C18 1.385(5) . ?
C13 C14 1.385(5) . ?
C14 C15 1.382(4) . ?
C14 H14A 0.9300 . ?
C15 C16 1.364(6) . ?
C15 H15A 0.9300 . ?
C16 C17 1.352(7) . ?
C16 H16A 0.9300 . ?
C17 C18 1.383(6) . ?
C17 H17A 0.9300 . ?
C18 H18A 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
N2 Pd1 C1 79.70(10) . . ?
N2 Pd1 N3 78.70(9) . . ?
C1 Pd1 N3 158.12(10) . . ?
N2 Pd1 Br1 173.13(6) . . ?
C1 Pd1 Br1 93.93(8) . . ?
N3 Pd1 Br1 107.48(6) . . ?
N2 N1 C6 110.5(2) . . ?
N1 N2 C7 119.7(2) . . ?
N1 N2 Pd1 120.52(18) . . ?
C7 N2 Pd1 119.73(17) . . ?
N4 N3 C12 111.5(2) . . ?
N4 N3 Pd1 137.3(2) . . ?
C12 N3 Pd1 108.80(16) . . ?
N3 N4 C13 116.3(3) . . ?
C2 C1 C6 117.5(3) . . ?
C2 C1 Pd1 132.6(2) . . ?
C6 C1 Pd1 109.90(19) . . ?
C1 C2 C3 120.2(3) . . ?
C1 C2 H2A 119.9 . . ?
C3 C2 H2A 119.9 . . ?
C4 C3 C2 121.5(3) . . ?
C4 C3 H3A 119.3 . . ?
C2 C3 H3A 119.3 . . ?
C5 C4 C3 120.2(3) . . ?
C5 C4 H4A 119.9 . . ?
C3 C4 H4A 119.9 . . ?
C4 C5 C6 118.5(3) . . ?
C4 C5 H5A 120.7 . . ?
C6 C5 H5A 120.7 . . ?
N1 C6 C5 118.6(3) . . ?
N1 C6 C1 119.4(2) . . ?
C5 C6 C1 122.0(3) . . ?
C8 C7 N2 123.9(3) . . ?
C8 C7 C12 120.2(3) . . ?
N2 C7 C12 115.9(2) . . ?
C9 C8 C7 119.4(3) . . ?
C9 C8 H8A 120.3 . . ?
C7 C8 H8A 120.3 . . ?
C8 C9 C10 120.6(3) . . ?
C8 C9 H9A 119.7 . . ?
C10 C9 H9A 119.7 . . ?
C9 C10 C11 121.1(3) . . ?
C9 C10 H10A 119.5 . . ?
C11 C10 H10A 119.5 . . ?
C10 C11 C12 119.5(3) . . ?
C10 C11 H11A 120.3 . . ?
C12 C11 H11A 120.3 . . ?
C11 C12 C7 119.2(3) . . ?
C11 C12 N3 123.9(3) . . ?
C7 C12 N3 116.9(2) . . ?
C18 C13 C14 120.5(3) . . ?
C18 C13 N4 116.4(3) . . ?
C14 C13 N4 122.6(3) . . ?
C15 C14 C13 119.0(4) . . ?
C15 C14 H14A 120.5 . . ?
C13 C14 H14A 120.5 . . ?
C16 C15 C14 119.7(4) . . ?
C16 C15 H15A 120.2 . . ?
C14 C15 H15A 120.2 . . ?
C17 C16 C15 121.9(4) . . ?
C17 C16 H16A 119.0 . . ?
C15 C16 H16A 119.0 . . ?
C16 C17 C18 119.6(4) . . ?
C16 C17 H17A 120.2 . . ?
C18 C17 H17A 120.2 . . ?
C17 C18 C13 119.2(4) . . ?
C17 C18 H18A 120.4 . . ?
C13 C18 H18A 120.4 . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        28.16
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.622
_refine_diff_density_min         -0.942
_refine_diff_density_rms         0.081

####################################################################### 
# 
# 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_4
_database_code_depnum_ccdc_archive 'CCDC 1031479'
_audit_update_record             
;
2014-10-29 deposited with the CCDC.
2015-02-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H13 I N4 Pd'
_chemical_formula_sum            'C18 H13 I N4 Pd'
_chemical_formula_weight         518.62

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'
Pd Pd -0.9988 1.0072 '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'

_symmetry_cell_setting           MOnoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   P2(1)/c
_symmetry_Int_Tables_number      14

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

_cell_length_a                   9.7153(5)
_cell_length_b                   11.3018(5)
_cell_length_c                   15.5241(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 93.107(2)
_cell_angle_gamma                90.00
_cell_volume                     1702.05(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1024
_cell_measurement_theta_min      2.10
_cell_measurement_theta_max      29.82

_exptl_crystal_description       parallelopiped
_exptl_crystal_colour            Red
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.14
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.024
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             992
_exptl_absorpt_coefficient_mu    2.910
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.436
_exptl_absorpt_correction_T_max  0.665
_exptl_absorpt_process_details   'Sadabs(Sheldrick, 1996)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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  'CCD area-detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            32806
_diffrn_reflns_av_R_equivalents  0.0506
_diffrn_reflns_av_sigmaI/netI    0.0327
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.10
_diffrn_reflns_theta_max         29.82
_reflns_number_total             4791
_reflns_number_gt                3849
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'SMART APEX II (Bruker,2010)'
_computing_cell_refinement       'SMART APEX II'
_computing_data_reduction        'SAINT (Bruker,2000)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Ortep-3v2 for windows (Farrugia, 1997)'
_computing_publication_material  'PLATON (Spek, 2008)'

_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 > 2sigma(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)+(0.0430P)²+6.3531P] 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         4791
_refine_ls_number_parameters     217
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0564
_refine_ls_R_factor_gt           0.0413
_refine_ls_wR_factor_ref         0.1101
_refine_ls_wR_factor_gt          0.0964
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_restrained_S_all      1.047
_refine_ls_shift/su_max          0.001
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Pd1 Pd 0.66432(4) 0.85650(3) 0.060677(19) 0.03205(10) Uani 1 1 d . . .
I1 I 0.70802(4) 0.69194(3) 0.17504(2) 0.04843(12) Uani 1 1 d . . .
N1 N 0.5725(4) 0.9183(3) -0.1104(2) 0.0400(8) Uani 1 1 d . . .
N2 N 0.6494(4) 0.9517(3) -0.0460(2) 0.0350(8) Uani 1 1 d . . .
N3 N 0.8072(4) 1.0033(3) 0.0942(2) 0.0353(8) Uani 1 1 d . . .
N4 N 0.8782(4) 1.0409(4) 0.1586(3) 0.0424(9) Uani 1 1 d . . .
C1 C 0.5224(5) 0.7653(4) -0.0079(3) 0.0354(9) Uani 1 1 d . . .
C2 C 0.4451(6) 0.6674(5) 0.0101(3) 0.0434(11) Uani 1 1 d . . .
H2 H 0.4575 0.6305 0.0635 0.052 Uiso 1 1 calc R . .
C3 C 0.3480(6) 0.6228(5) -0.0510(3) 0.0495(12) Uani 1 1 d . . .
H3 H 0.2948 0.5578 -0.0372 0.059 Uiso 1 1 calc R . .
C4 C 0.3299(6) 0.6734(5) -0.1313(3) 0.0486(12) Uani 1 1 d . . .
H4 H 0.2666 0.6413 -0.1718 0.058 Uiso 1 1 calc R . .
C5 C 0.4049(5) 0.7710(5) -0.1517(3) 0.0442(11) Uani 1 1 d . . .
H5 H 0.3931 0.8054 -0.2060 0.053 Uiso 1 1 calc R . .
C6 C 0.4989(5) 0.8178(4) -0.0901(3) 0.0351(9) Uani 1 1 d . . .
C7 C 0.7431(5) 1.0445(4) -0.0548(3) 0.0362(9) Uani 1 1 d . . .
C8 C 0.7532(6) 1.1085(5) -0.1306(3) 0.0487(12) Uani 1 1 d . . .
H8 H 0.6943 1.0924 -0.1784 0.058 Uiso 1 1 calc R . .
C9 C 0.8507(7) 1.1956(5) -0.1344(4) 0.0564(15) Uani 1 1 d . . .
H9 H 0.8583 1.2385 -0.1850 0.068 Uiso 1 1 calc R . .
C10 C 0.9372(6) 1.2201(5) -0.0637(4) 0.0527(13) Uani 1 1 d . . .
H10 H 1.0038 1.2788 -0.0673 0.063 Uiso 1 1 calc R . .
C11 C 0.9266(6) 1.1587(4) 0.0125(3) 0.0451(11) Uani 1 1 d . . .
H11 H 0.9847 1.1768 0.0603 0.054 Uiso 1 1 calc R . .
C12 C 0.8291(5) 1.0700(4) 0.0175(3) 0.0366(9) Uani 1 1 d . . .
C13 C 0.8522(5) 0.9925(4) 0.2400(3) 0.0369(9) Uani 1 1 d . . .
C14 C 0.7212(5) 0.9686(4) 0.2664(3) 0.0397(10) Uani 1 1 d . . .
H14 H 0.6447 0.9779 0.2284 0.048 Uiso 1 1 calc R . .
C15 C 0.7057(6) 0.9311(5) 0.3494(3) 0.0459(11) Uani 1 1 d . . .
H15 H 0.6179 0.9170 0.3683 0.055 Uiso 1 1 calc R . .
C16 C 0.8197(7) 0.9142(5) 0.4048(3) 0.0526(13) Uani 1 1 d . . .
H16 H 0.8087 0.8851 0.4600 0.063 Uiso 1 1 calc R . .
C17 C 0.9478(7) 0.9397(6) 0.3794(4) 0.0564(14) Uani 1 1 d . . .
H17 H 1.0242 0.9280 0.4173 0.068 Uiso 1 1 calc R . .
C18 C 0.9650(6) 0.9832(5) 0.2969(3) 0.0486(12) Uani 1 1 d . . .
H18 H 1.0519 1.0056 0.2804 0.058 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 N2 1.973(4) . ?
Pd1 C1 1.984(5) . ?
Pd1 N3 2.207(4) . ?
Pd1 I1 2.5903(4) . ?
N1 N2 1.272(5) . ?
N1 C6 1.387(6) . ?
N2 C7 1.401(6) . ?
N3 N4 1.258(5) . ?
N3 C12 1.435(5) . ?
N4 C13 1.413(6) . ?
C1 C2 1.375(6) . ?
C1 C6 1.416(6) . ?
C2 C3 1.395(7) . ?
C2 H2 0.9300 . ?
C3 C4 1.374(8) . ?
C3 H3 0.9300 . ?
C4 C5 1.368(8) . ?
C4 H4 0.9300 . ?
C5 C6 1.390(7) . ?
C5 H5 0.9300 . ?
C7 C8 1.390(6) . ?
C7 C12 1.393(7) . ?
C8 C9 1.369(8) . ?
C8 H8 0.9300 . ?
C9 C10 1.373(9) . ?
C9 H9 0.9300 . ?
C10 C11 1.381(7) . ?
C10 H10 0.9300 . ?
C11 C12 1.384(7) . ?
C11 H11 0.9300 . ?
C13 C18 1.374(7) . ?
C13 C14 1.384(7) . ?
C14 C15 1.372(7) . ?
C14 H14 0.9300 . ?
C15 C16 1.379(8) . ?
C15 H15 0.9300 . ?
C16 C17 1.357(9) . ?
C16 H16 0.9300 . ?
C17 C18 1.391(8) . ?
C17 H17 0.9300 . ?
C18 H18 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
N2 Pd1 C1 79.39(17) . . ?
N2 Pd1 N3 78.75(14) . . ?
C1 Pd1 N3 157.95(16) . . ?
N2 Pd1 I1 165.56(11) . . ?
C1 Pd1 I1 94.46(13) . . ?
N3 Pd1 I1 107.48(10) . . ?
N2 N1 C6 110.7(4) . . ?
N1 N2 C7 120.1(4) . . ?
N1 N2 Pd1 120.7(3) . . ?
C7 N2 Pd1 118.2(3) . . ?
N4 N3 C12 112.4(4) . . ?
N4 N3 Pd1 138.8(3) . . ?
C12 N3 Pd1 108.6(3) . . ?
N3 N4 C13 117.6(4) . . ?
C2 C1 C6 117.2(4) . . ?
C2 C1 Pd1 132.9(4) . . ?
C6 C1 Pd1 109.8(3) . . ?
C1 C2 C3 120.6(5) . . ?
C1 C2 H2 119.7 . . ?
C3 C2 H2 119.7 . . ?
C4 C3 C2 121.0(5) . . ?
C4 C3 H3 119.5 . . ?
C2 C3 H3 119.5 . . ?
C5 C4 C3 120.1(5) . . ?
C5 C4 H4 119.9 . . ?
C3 C4 H4 119.9 . . ?
C4 C5 C6 119.1(5) . . ?
C4 C5 H5 120.5 . . ?
C6 C5 H5 120.5 . . ?
N1 C6 C5 118.9(4) . . ?
N1 C6 C1 119.2(4) . . ?
C5 C6 C1 121.9(4) . . ?
C8 C7 C12 120.6(4) . . ?
C8 C7 N2 123.3(4) . . ?
C12 C7 N2 116.1(4) . . ?
C9 C8 C7 119.4(5) . . ?
C9 C8 H8 120.3 . . ?
C7 C8 H8 120.3 . . ?
C8 C9 C10 120.4(5) . . ?
C8 C9 H9 119.8 . . ?
C10 C9 H9 119.8 . . ?
C9 C10 C11 120.8(5) . . ?
C9 C10 H10 119.6 . . ?
C11 C10 H10 119.6 . . ?
C10 C11 C12 119.7(5) . . ?
C10 C11 H11 120.2 . . ?
C12 C11 H11 120.2 . . ?
C11 C12 C7 119.2(4) . . ?
C11 C12 N3 124.1(4) . . ?
C7 C12 N3 116.8(4) . . ?
C18 C13 C14 120.6(4) . . ?
C18 C13 N4 115.4(5) . . ?
C14 C13 N4 123.6(4) . . ?
C15 C14 C13 119.2(5) . . ?
C15 C14 H14 120.4 . . ?
C13 C14 H14 120.4 . . ?
C14 C15 C16 120.2(5) . . ?
C14 C15 H15 119.9 . . ?
C16 C15 H15 119.9 . . ?
C17 C16 C15 120.6(5) . . ?
C17 C16 H16 119.7 . . ?
C15 C16 H16 119.7 . . ?
C16 C17 C18 120.0(5) . . ?
C16 C17 H17 120.0 . . ?
C18 C17 H17 120.0 . . ?
C13 C18 C17 119.2(5) . . ?
C13 C18 H18 120.4 . . ?
C17 C18 H18 120.4 . . ?

_diffrn_measured_fraction_theta_max 0.982
_diffrn_reflns_theta_full        29.82
_diffrn_measured_fraction_theta_full 0.982
_refine_diff_density_max         1.754
_refine_diff_density_min         -1.004
_refine_diff_density_rms         0.140

