# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1435377'
_audit_update_record             
;
2015-11-05 deposited with the CCDC.
2016-01-08 downloaded from the CCDC.
;


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C30 H24 Cl2 Co N8'
_chemical_formula_sum            'C30 H24 Cl2 Co N8'
_chemical_formula_weight         626.40

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'
Co Co 0.3494 0.9721 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'

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                   8.9080(8)
_cell_length_b                   10.6498(10)
_cell_length_c                   14.8620(15)
_cell_angle_alpha                90.00
_cell_angle_beta                 96.901(2)
_cell_angle_gamma                90.00
_cell_volume                     1399.7(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    6112
_cell_measurement_theta_min      2.76
_cell_measurement_theta_max      30.47

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.486
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             642
_exptl_absorpt_coefficient_mu    0.841
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8617
_exptl_absorpt_correction_T_max  0.9059
_exptl_absorpt_process_details   
;
program SADABS, Bruker (2001).
;
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  
;
 Bruker-Nonius X8kappa APEX II CCD area detector
;
_diffrn_measurement_method       'phi and omega scans with narrow frames'
_diffrn_detector_area_resol_mean 8.26
_diffrn_standards_decay_%        0
_diffrn_reflns_number            16755
_diffrn_reflns_av_R_equivalents  0.0268
_diffrn_reflns_av_sigmaI/netI    0.0280
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.36
_diffrn_reflns_theta_max         30.49
_reflns_number_total             4249
_reflns_number_gt                3535
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 Software Suite (Bruker, 2007)'
_computing_cell_refinement       'APEX2 Software Suite (Bruker, 2007)'
_computing_data_reduction        'APEX2 Software Suite (Bruker, 2007)'
_computing_structure_solution    'SIR2002 (Burla et al., 2003)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL and publCIF (Westrip, 2010)'

_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)+(0.0488P)²+0.2817P] 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         4249
_refine_ls_number_parameters     187
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0441
_refine_ls_R_factor_gt           0.0342
_refine_ls_wR_factor_ref         0.0892
_refine_ls_wR_factor_gt          0.0838
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.015
_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
Co1 Co 0.0000 0.5000 0.0000 0.01813(8) Uani 1 2 d SU . .
Cl1 Cl -0.09121(4) 0.57409(3) 0.13884(2) 0.02633(9) Uani 1 1 d U . .
N1 N -0.04366(13) 0.23674(10) 0.08377(8) 0.0217(2) Uani 1 1 d U . .
N2 N -0.09551(13) 0.31662(11) 0.01483(8) 0.0217(2) Uani 1 1 d U . .
N3 N 0.19625(13) 0.32727(11) 0.13738(8) 0.0217(2) Uani 1 1 d U . .
N4 N 0.20094(13) 0.42521(11) 0.07818(8) 0.0215(2) Uani 1 1 d U . .
C1 C -0.19084(17) 0.25161(14) -0.04187(10) 0.0268(3) Uani 1 1 d U . .
H1 H -0.2417 0.2839 -0.0969 0.032 Uiso 1 1 calc R . .
C2 C -0.20763(17) 0.12767(13) -0.01030(10) 0.0259(3) Uani 1 1 d U . .
C3 C -0.2963(2) 0.02245(16) -0.04025(12) 0.0371(4) Uani 1 1 d U . .
H3 H -0.3641 0.0252 -0.0947 0.045 Uiso 1 1 calc R . .
C4 C -0.2810(2) -0.08399(16) 0.01218(13) 0.0413(4) Uani 1 1 d U . .
H4 H -0.3402 -0.1557 -0.0062 0.050 Uiso 1 1 calc R . .
C5 C -0.1795(2) -0.08960(15) 0.09274(13) 0.0396(4) Uani 1 1 d U . .
H5 H -0.1709 -0.1656 0.1264 0.048 Uiso 1 1 calc R . .
C6 C -0.0927(2) 0.01173(14) 0.12379(12) 0.0320(3) Uani 1 1 d U . .
H6 H -0.0248 0.0079 0.1781 0.038 Uiso 1 1 calc R . .
C7 C -0.10970(16) 0.12104(13) 0.07105(9) 0.0226(3) Uani 1 1 d U . .
C8 C 0.34554(16) 0.44754(14) 0.07244(9) 0.0240(3) Uani 1 1 d U . .
H8 H 0.3816 0.5103 0.0350 0.029 Uiso 1 1 calc R . .
C9 C 0.43965(16) 0.36576(13) 0.12946(9) 0.0229(3) Uani 1 1 d U . .
C10 C 0.59731(17) 0.34951(16) 0.15136(10) 0.0301(3) Uani 1 1 d U . .
H10 H 0.6674 0.4026 0.1265 0.036 Uiso 1 1 calc R . .
C11 C 0.64509(17) 0.25434(18) 0.20978(11) 0.0348(4) Uani 1 1 d U . .
H11 H 0.7505 0.2413 0.2255 0.042 Uiso 1 1 calc R . .
C12 C 0.54209(18) 0.17519(17) 0.24713(11) 0.0338(3) Uani 1 1 d U . .
H12 H 0.5802 0.1084 0.2857 0.041 Uiso 1 1 calc R . .
C13 C 0.38819(17) 0.19128(15) 0.22975(10) 0.0283(3) Uani 1 1 d U . .
H13 H 0.3193 0.1394 0.2568 0.034 Uiso 1 1 calc R . .
C14 C 0.33883(15) 0.28857(13) 0.16990(9) 0.0216(3) Uani 1 1 d U . .
C15 C 0.05224(15) 0.28446(13) 0.16174(9) 0.0214(3) Uani 1 1 d U . .
H15A H 0.0696 0.2174 0.2080 0.026 Uiso 1 1 calc R . .
H15B H 0.0005 0.3550 0.1886 0.026 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
Co1 N2 2.1521(12) 3_565 ?
Co1 N2 2.1521(12) . ?
Co1 N4 2.1653(12) 3_565 ?
Co1 N4 2.1653(12) . ?
Co1 Cl1 2.4379(4) 3_565 ?
Co1 Cl1 2.4379(4) . ?
N1 N2 1.3686(15) . ?
N1 C7 1.3687(17) . ?
N1 C15 1.4466(17) . ?
N2 C1 1.3186(18) . ?
N3 C14 1.3672(17) . ?
N3 N4 1.3685(15) . ?
N3 C15 1.4478(17) . ?
N4 C8 1.3227(18) . ?
C1 C2 1.415(2) . ?
C1 H1 0.9500 . ?
C2 C7 1.405(2) . ?
C2 C3 1.412(2) . ?
C3 C4 1.373(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.412(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.375(2) . ?
C5 H5 0.9500 . ?
C6 C7 1.401(2) . ?
C6 H6 0.9500 . ?
C8 C9 1.417(2) . ?
C8 H8 0.9500 . ?
C9 C14 1.4048(19) . ?
C9 C10 1.414(2) . ?
C10 C11 1.369(2) . ?
C10 H10 0.9500 . ?
C11 C12 1.408(2) . ?
C11 H11 0.9500 . ?
C12 C13 1.375(2) . ?
C12 H12 0.9500 . ?
C13 C14 1.401(2) . ?
C13 H13 0.9500 . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?

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 Co1 N2 180.00(6) 3_565 . ?
N2 Co1 N4 85.57(4) 3_565 3_565 ?
N2 Co1 N4 94.43(4) . 3_565 ?
N2 Co1 N4 94.43(4) 3_565 . ?
N2 Co1 N4 85.57(4) . . ?
N4 Co1 N4 180.00(8) 3_565 . ?
N2 Co1 Cl1 91.78(3) 3_565 3_565 ?
N2 Co1 Cl1 88.22(3) . 3_565 ?
N4 Co1 Cl1 90.17(3) 3_565 3_565 ?
N4 Co1 Cl1 89.83(3) . 3_565 ?
N2 Co1 Cl1 88.22(3) 3_565 . ?
N2 Co1 Cl1 91.78(3) . . ?
N4 Co1 Cl1 89.83(3) 3_565 . ?
N4 Co1 Cl1 90.17(3) . . ?
Cl1 Co1 Cl1 180.000(15) 3_565 . ?
N2 N1 C7 110.82(11) . . ?
N2 N1 C15 119.67(10) . . ?
C7 N1 C15 129.02(12) . . ?
C1 N2 N1 106.59(11) . . ?
C1 N2 Co1 130.03(10) . . ?
N1 N2 Co1 122.60(8) . . ?
C14 N3 N4 110.99(11) . . ?
C14 N3 C15 129.06(12) . . ?
N4 N3 C15 119.81(11) . . ?
C8 N4 N3 106.48(11) . . ?
C8 N4 Co1 130.38(9) . . ?
N3 N4 Co1 122.56(9) . . ?
N2 C1 C2 111.32(13) . . ?
N2 C1 H1 124.3 . . ?
C2 C1 H1 124.3 . . ?
C7 C2 C3 119.83(14) . . ?
C7 C2 C1 104.64(12) . . ?
C3 C2 C1 135.51(15) . . ?
C4 C3 C2 117.55(16) . . ?
C4 C3 H3 121.2 . . ?
C2 C3 H3 121.2 . . ?
C3 C4 C5 121.74(15) . . ?
C3 C4 H4 119.1 . . ?
C5 C4 H4 119.1 . . ?
C6 C5 C4 121.89(15) . . ?
C6 C5 H5 119.1 . . ?
C4 C5 H5 119.1 . . ?
C5 C6 C7 116.47(15) . . ?
C5 C6 H6 121.8 . . ?
C7 C6 H6 121.8 . . ?
N1 C7 C6 130.90(14) . . ?
N1 C7 C2 106.60(12) . . ?
C6 C7 C2 122.49(13) . . ?
N4 C8 C9 111.20(12) . . ?
N4 C8 H8 124.4 . . ?
C9 C8 H8 124.4 . . ?
C14 C9 C10 119.90(13) . . ?
C14 C9 C8 104.64(12) . . ?
C10 C9 C8 135.46(13) . . ?
C11 C10 C9 117.47(14) . . ?
C11 C10 H10 121.3 . . ?
C9 C10 H10 121.3 . . ?
C10 C11 C12 121.71(14) . . ?
C10 C11 H11 119.1 . . ?
C12 C11 H11 119.1 . . ?
C13 C12 C11 122.24(14) . . ?
C13 C12 H12 118.9 . . ?
C11 C12 H12 118.9 . . ?
C12 C13 C14 116.17(14) . . ?
C12 C13 H13 121.9 . . ?
C14 C13 H13 121.9 . . ?
N3 C14 C13 130.88(13) . . ?
N3 C14 C9 106.67(12) . . ?
C13 C14 C9 122.43(13) . . ?
N1 C15 N3 111.48(11) . . ?
N1 C15 H15A 109.3 . . ?
N3 C15 H15A 109.3 . . ?
N1 C15 H15B 109.3 . . ?
N3 C15 H15B 109.3 . . ?
H15A C15 H15B 108.0 . . ?

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
C7 N1 N2 C1 -1.27(16) . . . . ?
C15 N1 N2 C1 -173.87(12) . . . . ?
C7 N1 N2 Co1 -172.09(9) . . . . ?
C15 N1 N2 Co1 15.31(16) . . . . ?
N4 Co1 N2 C1 34.80(13) 3_565 . . . ?
N4 Co1 N2 C1 -145.20(13) . . . . ?
Cl1 Co1 N2 C1 -55.24(13) 3_565 . . . ?
Cl1 Co1 N2 C1 124.76(13) . . . . ?
N4 Co1 N2 N1 -156.73(10) 3_565 . . . ?
N4 Co1 N2 N1 23.27(10) . . . . ?
Cl1 Co1 N2 N1 113.24(10) 3_565 . . . ?
Cl1 Co1 N2 N1 -66.76(10) . . . . ?
C14 N3 N4 C8 0.67(15) . . . . ?
C15 N3 N4 C8 176.82(12) . . . . ?
C14 N3 N4 Co1 172.84(9) . . . . ?
C15 N3 N4 Co1 -11.01(16) . . . . ?
N2 Co1 N4 C8 -35.29(13) 3_565 . . . ?
N2 Co1 N4 C8 144.71(13) . . . . ?
Cl1 Co1 N4 C8 56.48(13) 3_565 . . . ?
Cl1 Co1 N4 C8 -123.52(13) . . . . ?
N2 Co1 N4 N3 154.58(10) 3_565 . . . ?
N2 Co1 N4 N3 -25.42(10) . . . . ?
Cl1 Co1 N4 N3 -113.65(10) 3_565 . . . ?
Cl1 Co1 N4 N3 66.35(10) . . . . ?
N1 N2 C1 C2 1.69(17) . . . . ?
Co1 N2 C1 C2 171.57(10) . . . . ?
N2 C1 C2 C7 -1.46(17) . . . . ?
N2 C1 C2 C3 176.87(18) . . . . ?
C7 C2 C3 C4 -0.7(3) . . . . ?
C1 C2 C3 C4 -178.86(19) . . . . ?
C2 C3 C4 C5 -0.6(3) . . . . ?
C3 C4 C5 C6 1.2(3) . . . . ?
C4 C5 C6 C7 -0.3(3) . . . . ?
N2 N1 C7 C6 -179.30(16) . . . . ?
C15 N1 C7 C6 -7.6(3) . . . . ?
N2 N1 C7 C2 0.36(16) . . . . ?
C15 N1 C7 C2 172.09(13) . . . . ?
C5 C6 C7 N1 178.48(16) . . . . ?
C5 C6 C7 C2 -1.1(2) . . . . ?
C3 C2 C7 N1 -178.03(14) . . . . ?
C1 C2 C7 N1 0.62(16) . . . . ?
C3 C2 C7 C6 1.7(2) . . . . ?
C1 C2 C7 C6 -179.68(15) . . . . ?
N3 N4 C8 C9 -1.12(16) . . . . ?
Co1 N4 C8 C9 -172.45(9) . . . . ?
N4 C8 C9 C14 1.14(16) . . . . ?
N4 C8 C9 C10 -178.35(16) . . . . ?
C14 C9 C10 C11 2.3(2) . . . . ?
C8 C9 C10 C11 -178.28(17) . . . . ?
C9 C10 C11 C12 -0.1(2) . . . . ?
C10 C11 C12 C13 -2.3(3) . . . . ?
C11 C12 C13 C14 2.2(3) . . . . ?
N4 N3 C14 C13 -178.55(14) . . . . ?
C15 N3 C14 C13 5.8(3) . . . . ?
N4 N3 C14 C9 0.04(15) . . . . ?
C15 N3 C14 C9 -175.66(13) . . . . ?
C12 C13 C14 N3 178.48(15) . . . . ?
C12 C13 C14 C9 0.1(2) . . . . ?
C10 C9 C14 N3 178.91(13) . . . . ?
C8 C9 C14 N3 -0.68(15) . . . . ?
C10 C9 C14 C13 -2.4(2) . . . . ?
C8 C9 C14 C13 178.05(14) . . . . ?
N2 N1 C15 N3 -65.55(16) . . . . ?
C7 N1 C15 N3 123.36(14) . . . . ?
C14 N3 C15 N1 -121.79(15) . . . . ?
N4 N3 C15 N1 62.84(16) . . . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        30.49
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.218
_refine_diff_density_min         -0.223
_refine_diff_density_rms         0.065
####################################################################### 
# 
# 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_1a
_database_code_depnum_ccdc_archive 'CCDC 1435378'
_audit_update_record             
;
2015-11-05 deposited with the CCDC.
2016-01-08 downloaded from the CCDC.
;



_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H18 Cl Co N4 O3, Cl, H2 O'
_chemical_formula_sum            'C15 H20 Cl2 Co N4 O4'
_chemical_formula_weight         450.18

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'
Co Co 0.3494 0.9721 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.3480(10)
_cell_length_b                   10.8244(13)
_cell_length_c                   12.3168(15)
_cell_angle_alpha                71.218(3)
_cell_angle_beta                 74.121(3)
_cell_angle_gamma                68.217(3)
_cell_volume                     963.3(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    291(2)
_cell_measurement_reflns_used    2640
_cell_measurement_theta_min      2.38
_cell_measurement_theta_max      23.36

_exptl_crystal_description       plate
_exptl_crystal_colour            pink
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.552
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             462
_exptl_absorpt_coefficient_mu    1.196
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8410
_exptl_absorpt_correction_T_max  0.8898
_exptl_absorpt_process_details   
;
program SADABS, Bruker (2001).
;
_diffrn_ambient_temperature      291(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  
;
 Bruker-Nonius X8kappa APEX II CCD area detector
;
_diffrn_measurement_method       'phi and omega scans with narrow frames'
_diffrn_detector_area_resol_mean 8.26
_diffrn_standards_decay_%        0
_diffrn_reflns_number            8578
_diffrn_reflns_av_R_equivalents  0.0379
_diffrn_reflns_av_sigmaI/netI    0.0466
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.09
_diffrn_reflns_theta_max         25.25
_reflns_number_total             3358
_reflns_number_gt                2544
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 Software Suite (Bruker, 2007)'
_computing_cell_refinement       'APEX2 Software Suite (Bruker, 2007)'
_computing_data_reduction        'APEX2 Software Suite (Bruker, 2007)'
_computing_structure_solution    'SIR2002 (Burla et al., 2003)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL and publCIF (Westrip, 2010)'

_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)+(0.0707P)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    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3358
_refine_ls_number_parameters     259
_refine_ls_number_restraints     12
_refine_ls_R_factor_all          0.0637
_refine_ls_R_factor_gt           0.0441
_refine_ls_wR_factor_ref         0.1195
_refine_ls_wR_factor_gt          0.1111
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_restrained_S_all      1.034
_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
Co1 Co 0.70176(6) 0.39977(4) 0.19087(4) 0.03959(18) Uani 1 1 d . . .
Cl1 Cl 0.73218(12) 0.55105(9) -0.00264(7) 0.0493(2) Uani 1 1 d . . .
O1 O 0.9592(3) 0.3798(3) 0.1977(2) 0.0525(6) Uani 1 1 d D . .
H1A H 1.031(4) 0.405(4) 0.136(2) 0.063 Uiso 1 1 d D . .
H1B H 0.949(5) 0.402(4) 0.258(2) 0.063 Uiso 1 1 d D . .
O2 O 0.6130(4) 0.5600(3) 0.2789(3) 0.0622(7) Uani 1 1 d D . .
H2A H 0.686(4) 0.564(4) 0.315(3) 0.075 Uiso 1 1 d D . .
H2B H 0.507(3) 0.612(4) 0.300(3) 0.075 Uiso 1 1 d D . .
O3 O 0.4352(3) 0.4346(3) 0.2014(2) 0.0505(6) Uani 1 1 d D . .
H3A H 0.366(4) 0.504(3) 0.232(3) 0.061 Uiso 1 1 d D . .
H3B H 0.397(5) 0.443(3) 0.136(2) 0.061 Uiso 1 1 d D . .
N1 N 0.8435(4) 0.0995(3) 0.1719(2) 0.0421(7) Uani 1 1 d . . .
N2 N 0.7655(4) 0.2322(3) 0.1156(2) 0.0405(6) Uani 1 1 d . . .
N3 N 0.7991(4) 0.1150(3) 0.3673(2) 0.0463(7) Uani 1 1 d . . .
N4 N 0.7008(4) 0.2494(3) 0.3590(2) 0.0450(7) Uani 1 1 d . . .
C1 C 0.5917(5) 0.2555(4) 0.4575(3) 0.0538(9) Uani 1 1 d . . .
H1 H 0.5091 0.3356 0.4744 0.065 Uiso 1 1 calc R . .
C2 C 0.6162(5) 0.1239(4) 0.5349(3) 0.0502(9) Uani 1 1 d . . .
C3 C 0.5381(6) 0.0686(5) 0.6485(3) 0.0671(12) Uani 1 1 d . . .
H3 H 0.4499 0.1255 0.6917 0.081 Uiso 1 1 calc R . .
C4 C 0.5941(6) -0.0686(5) 0.6934(3) 0.0668(12) Uani 1 1 d . . .
H4 H 0.5428 -0.1064 0.7678 0.080 Uiso 1 1 calc R . .
C5 C 0.7031(5) 0.2271(3) 0.0305(3) 0.0431(8) Uani 1 1 d . . .
H5 H 0.6439 0.3035 -0.0214 0.052 Uiso 1 1 calc R . .
C6 C 0.7384(4) 0.0902(3) 0.0287(3) 0.0417(8) Uani 1 1 d . . .
C7 C 0.7041(5) 0.0247(4) -0.0417(3) 0.0537(10) Uani 1 1 d . . .
H7 H 0.6458 0.0758 -0.1041 0.064 Uiso 1 1 calc R . .
C8 C 0.7586(5) -0.1138(4) -0.0152(4) 0.0604(11) Uani 1 1 d . . .
H8 H 0.7370 -0.1583 -0.0603 0.072 Uiso 1 1 calc R . .
C9 C 0.8462(6) -0.1915(4) 0.0776(4) 0.0630(12) Uani 1 1 d . . .
H9 H 0.8793 -0.2867 0.0933 0.076 Uiso 1 1 calc R . .
C10 C 0.8861(5) -0.1338(4) 0.1473(3) 0.0537(9) Uani 1 1 d . . .
H10 H 0.9472 -0.1866 0.2082 0.064 Uiso 1 1 calc R . .
C11 C 0.8286(4) 0.0102(3) 0.1205(3) 0.0401(8) Uani 1 1 d . . .
C12 C 0.7290(6) -0.1552(4) 0.6289(3) 0.0659(11) Uani 1 1 d . . .
H12 H 0.7637 -0.2492 0.6623 0.079 Uiso 1 1 calc R . .
C13 C 0.8103(5) -0.1072(4) 0.5203(3) 0.0582(10) Uani 1 1 d . . .
H13 H 0.9009 -0.1652 0.4792 0.070 Uiso 1 1 calc R . .
C14 C 0.7503(4) 0.0344(4) 0.4736(3) 0.0433(8) Uani 1 1 d . . .
C15 C 0.9261(4) 0.0731(4) 0.2695(3) 0.0463(8) Uani 1 1 d . . .
H15A H 0.9883 -0.0242 0.2924 0.056 Uiso 1 1 calc R . .
H15B H 1.0110 0.1225 0.2462 0.056 Uiso 1 1 calc R . .
Cl2 Cl 0.19862(13) 0.64049(11) 0.35902(9) 0.0658(3) Uani 1 1 d . . .
O4 O 0.9009(5) 0.5096(4) 0.3756(3) 0.0947(11) Uani 1 1 d D . .
H4A H 0.869(6) 0.460(5) 0.447(3) 0.114 Uiso 1 1 d D . .
H4B H 1.002(4) 0.519(5) 0.370(4) 0.114 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
Co1 O3 2.088(2) . ?
Co1 O1 2.101(2) . ?
Co1 N2 2.128(3) . ?
Co1 O2 2.133(2) . ?
Co1 N4 2.184(3) . ?
Co1 Cl1 2.4271(9) . ?
O1 H1A 0.863(17) . ?
O1 H1B 0.829(17) . ?
O2 H2A 0.868(18) . ?
O2 H2B 0.873(18) . ?
O3 H3A 0.882(17) . ?
O3 H3B 0.911(17) . ?
N1 C11 1.371(4) . ?
N1 N2 1.371(4) . ?
N1 C15 1.445(4) . ?
N2 C5 1.316(4) . ?
N3 N4 1.366(4) . ?
N3 C14 1.370(4) . ?
N3 C15 1.442(4) . ?
N4 C1 1.307(4) . ?
C1 C2 1.412(5) . ?
C1 H1 0.9300 . ?
C2 C14 1.401(5) . ?
C2 C3 1.412(5) . ?
C3 C4 1.352(6) . ?
C3 H3 0.9300 . ?
C4 C12 1.408(6) . ?
C4 H4 0.9300 . ?
C5 C6 1.406(5) . ?
C5 H5 0.9300 . ?
C6 C11 1.395(5) . ?
C6 C7 1.420(5) . ?
C7 C8 1.349(5) . ?
C7 H7 0.9300 . ?
C8 C9 1.390(6) . ?
C8 H8 0.9300 . ?
C9 C10 1.377(5) . ?
C9 H9 0.9300 . ?
C10 C11 1.402(5) . ?
C10 H10 0.9300 . ?
C12 C13 1.356(5) . ?
C12 H12 0.9300 . ?
C13 C14 1.397(5) . ?
C13 H13 0.9300 . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
O4 H4A 0.897(18) . ?
O4 H4B 0.868(19) . ?

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
O3 Co1 O1 172.19(10) . . ?
O3 Co1 N2 90.26(10) . . ?
O1 Co1 N2 97.06(11) . . ?
O3 Co1 O2 84.52(10) . . ?
O1 Co1 O2 87.98(11) . . ?
N2 Co1 O2 173.35(10) . . ?
O3 Co1 N4 90.77(10) . . ?
O1 Co1 N4 86.98(10) . . ?
N2 Co1 N4 86.40(10) . . ?
O2 Co1 N4 89.55(11) . . ?
O3 Co1 Cl1 93.80(7) . . ?
O1 Co1 Cl1 88.98(7) . . ?
N2 Co1 Cl1 89.79(7) . . ?
O2 Co1 Cl1 94.65(9) . . ?
N4 Co1 Cl1 174.07(8) . . ?
Co1 O1 H1A 122(3) . . ?
Co1 O1 H1B 104(3) . . ?
H1A O1 H1B 119(3) . . ?
Co1 O2 H2A 117(2) . . ?
Co1 O2 H2B 131(2) . . ?
H2A O2 H2B 110(3) . . ?
Co1 O3 H3A 114(2) . . ?
Co1 O3 H3B 118(2) . . ?
H3A O3 H3B 108(2) . . ?
C11 N1 N2 109.9(3) . . ?
C11 N1 C15 130.3(3) . . ?
N2 N1 C15 119.7(3) . . ?
C5 N2 N1 107.3(3) . . ?
C5 N2 Co1 128.5(2) . . ?
N1 N2 Co1 122.0(2) . . ?
N4 N3 C14 110.8(3) . . ?
N4 N3 C15 120.7(3) . . ?
C14 N3 C15 128.4(3) . . ?
C1 N4 N3 107.1(3) . . ?
C1 N4 Co1 130.5(3) . . ?
N3 N4 Co1 120.73(19) . . ?
N4 C1 C2 110.8(3) . . ?
N4 C1 H1 124.6 . . ?
C2 C1 H1 124.6 . . ?
C14 C2 C3 118.6(4) . . ?
C14 C2 C1 105.3(3) . . ?
C3 C2 C1 136.0(4) . . ?
C4 C3 C2 118.7(4) . . ?
C4 C3 H3 120.6 . . ?
C2 C3 H3 120.6 . . ?
C3 C4 C12 120.9(4) . . ?
C3 C4 H4 119.5 . . ?
C12 C4 H4 119.5 . . ?
N2 C5 C6 110.6(3) . . ?
N2 C5 H5 124.7 . . ?
C6 C5 H5 124.7 . . ?
C11 C6 C5 105.5(3) . . ?
C11 C6 C7 119.4(3) . . ?
C5 C6 C7 135.1(4) . . ?
C8 C7 C6 118.0(4) . . ?
C8 C7 H7 121.0 . . ?
C6 C7 H7 121.0 . . ?
C7 C8 C9 121.7(4) . . ?
C7 C8 H8 119.1 . . ?
C9 C8 H8 119.1 . . ?
C10 C9 C8 122.8(4) . . ?
C10 C9 H9 118.6 . . ?
C8 C9 H9 118.6 . . ?
C9 C10 C11 115.5(4) . . ?
C9 C10 H10 122.2 . . ?
C11 C10 H10 122.2 . . ?
N1 C11 C6 106.6(3) . . ?
N1 C11 C10 130.8(3) . . ?
C6 C11 C10 122.6(3) . . ?
C13 C12 C4 122.7(4) . . ?
C13 C12 H12 118.6 . . ?
C4 C12 H12 118.6 . . ?
C12 C13 C14 116.2(4) . . ?
C12 C13 H13 121.9 . . ?
C14 C13 H13 121.9 . . ?
N3 C14 C13 131.3(3) . . ?
N3 C14 C2 105.9(3) . . ?
C13 C14 C2 122.8(3) . . ?
N3 C15 N1 111.4(3) . . ?
N3 C15 H15A 109.4 . . ?
N1 C15 H15A 109.4 . . ?
N3 C15 H15B 109.4 . . ?
N1 C15 H15B 109.4 . . ?
H15A C15 H15B 108.0 . . ?
H4A O4 H4B 110(3) . . ?

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
C11 N1 N2 C5 -0.2(3) . . . . ?
C15 N1 N2 C5 179.3(3) . . . . ?
C11 N1 N2 Co1 164.3(2) . . . . ?
C15 N1 N2 Co1 -16.3(4) . . . . ?
O3 Co1 N2 C5 46.8(3) . . . . ?
O1 Co1 N2 C5 -135.9(3) . . . . ?
N4 Co1 N2 C5 137.5(3) . . . . ?
Cl1 Co1 N2 C5 -47.0(3) . . . . ?
O3 Co1 N2 N1 -114.1(2) . . . . ?
O1 Co1 N2 N1 63.2(2) . . . . ?
N4 Co1 N2 N1 -23.3(2) . . . . ?
Cl1 Co1 N2 N1 152.1(2) . . . . ?
C14 N3 N4 C1 0.2(4) . . . . ?
C15 N3 N4 C1 176.6(3) . . . . ?
C14 N3 N4 Co1 -166.6(2) . . . . ?
C15 N3 N4 Co1 9.8(4) . . . . ?
O3 Co1 N4 C1 -46.4(3) . . . . ?
O1 Co1 N4 C1 126.1(3) . . . . ?
N2 Co1 N4 C1 -136.7(3) . . . . ?
O2 Co1 N4 C1 38.1(3) . . . . ?
O3 Co1 N4 N3 116.8(2) . . . . ?
O1 Co1 N4 N3 -70.7(2) . . . . ?
N2 Co1 N4 N3 26.6(2) . . . . ?
O2 Co1 N4 N3 -158.7(2) . . . . ?
N3 N4 C1 C2 0.5(4) . . . . ?
Co1 N4 C1 C2 165.5(2) . . . . ?
N4 C1 C2 C14 -0.9(4) . . . . ?
N4 C1 C2 C3 -178.9(4) . . . . ?
C14 C2 C3 C4 -0.9(6) . . . . ?
C1 C2 C3 C4 176.9(4) . . . . ?
C2 C3 C4 C12 0.7(6) . . . . ?
N1 N2 C5 C6 0.1(3) . . . . ?
Co1 N2 C5 C6 -163.0(2) . . . . ?
N2 C5 C6 C11 0.0(4) . . . . ?
N2 C5 C6 C7 -179.7(3) . . . . ?
C11 C6 C7 C8 1.0(5) . . . . ?
C5 C6 C7 C8 -179.4(4) . . . . ?
C6 C7 C8 C9 -0.1(5) . . . . ?
C7 C8 C9 C10 -1.2(6) . . . . ?
C8 C9 C10 C11 1.5(5) . . . . ?
N2 N1 C11 C6 0.2(3) . . . . ?
C15 N1 C11 C6 -179.2(3) . . . . ?
N2 N1 C11 C10 -179.6(3) . . . . ?
C15 N1 C11 C10 1.1(5) . . . . ?
C5 C6 C11 N1 -0.1(3) . . . . ?
C7 C6 C11 N1 179.7(3) . . . . ?
C5 C6 C11 C10 179.7(3) . . . . ?
C7 C6 C11 C10 -0.6(5) . . . . ?
C9 C10 C11 N1 179.1(3) . . . . ?
C9 C10 C11 C6 -0.6(5) . . . . ?
C3 C4 C12 C13 0.4(7) . . . . ?
C4 C12 C13 C14 -1.3(6) . . . . ?
N4 N3 C14 C13 178.7(4) . . . . ?
C15 N3 C14 C13 2.6(6) . . . . ?
N4 N3 C14 C2 -0.7(4) . . . . ?
C15 N3 C14 C2 -176.8(3) . . . . ?
C12 C13 C14 N3 -178.2(3) . . . . ?
C12 C13 C14 C2 1.2(6) . . . . ?
C3 C2 C14 N3 179.4(3) . . . . ?
C1 C2 C14 N3 1.0(4) . . . . ?
C3 C2 C14 C13 -0.1(5) . . . . ?
C1 C2 C14 C13 -178.5(3) . . . . ?
N4 N3 C15 N1 -62.5(4) . . . . ?
C14 N3 C15 N1 113.2(4) . . . . ?
C11 N1 C15 N3 -113.9(3) . . . . ?
N2 N1 C15 N3 66.7(4) . . . . ?

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
O4 H4B Cl2 0.868(19) 2.41(3) 3.221(4) 155(5) 1_655
O4 H4A Cl2 0.897(18) 2.29(2) 3.180(4) 169(5) 2_666
O3 H3B Cl1 0.911(17) 2.173(19) 3.072(3) 169(3) 2_665
O3 H3A Cl2 0.882(17) 2.314(18) 3.171(3) 164(3) .
O2 H2B Cl2 0.873(18) 2.41(2) 3.185(3) 149(3) .
O2 H2A O4 0.868(18) 1.95(2) 2.770(4) 158(4) .
O1 H1B O4 0.829(17) 2.01(2) 2.812(4) 164(4) .
O1 H1A Cl1 0.863(17) 2.29(2) 3.140(3) 166(3) 2_765

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        25.25
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.530
_refine_diff_density_min         -0.321
_refine_diff_density_rms         0.078
####################################################################### 
# 
# 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 1435379'
_audit_update_record             
;
2015-11-05 deposited with the CCDC.
2016-01-08 downloaded from the CCDC.
;


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C30 H24 Cl2 N8 Ni'
_chemical_formula_sum            'C30 H24 Cl2 N8 Ni'
_chemical_formula_weight         626.18

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'
Ni Ni 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'

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                   8.933(2)
_cell_length_b                   10.599(2)
_cell_length_c                   14.768(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 96.790(11)
_cell_angle_gamma                90.00
_cell_volume                     1388.5(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    1663
_cell_measurement_theta_min      2.30
_cell_measurement_theta_max      19.83

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.498
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             644
_exptl_absorpt_coefficient_mu    0.928
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9129
_exptl_absorpt_correction_T_max  0.9551
_exptl_absorpt_process_details   
;
program SADABS, Bruker (2001).
;
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  
;
 Bruker-Nonius X8kappa APEX II CCD area detector
;
_diffrn_measurement_method       'phi and omega scans with narrow frames'
_diffrn_detector_area_resol_mean 8.26
_diffrn_standards_decay_%        0
_diffrn_reflns_number            23915
_diffrn_reflns_av_R_equivalents  0.0959
_diffrn_reflns_av_sigmaI/netI    0.0662
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.30
_diffrn_reflns_theta_max         25.25
_reflns_number_total             2503
_reflns_number_gt                1403
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 Software Suite (Bruker, 2007)'
_computing_cell_refinement       'APEX2 Software Suite (Bruker, 2007)'
_computing_data_reduction        'APEX2 Software Suite (Bruker, 2007)'
_computing_structure_solution    'SIR2002 (Burla et al., 2003)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL and publCIF (Westrip, 2010)'

_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)+(0.0563P)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     SHELXL
_refine_ls_extinction_coef       0.0158(18)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2503
_refine_ls_number_parameters     188
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1266
_refine_ls_R_factor_gt           0.0567
_refine_ls_wR_factor_ref         0.1338
_refine_ls_wR_factor_gt          0.1172
_refine_ls_goodness_of_fit_ref   0.921
_refine_ls_restrained_S_all      0.887
_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
Ni1 Ni 0.5000 0.5000 0.0000 0.0288(3) Uani 1 2 d SU . .
Cl1 Cl 0.40685(14) 0.42444(11) 0.13758(8) 0.0376(4) Uani 1 1 d . . .
N1 N 0.6920(4) 0.6677(3) 0.1377(2) 0.0333(10) Uani 1 1 d . . .
N2 N 0.6963(4) 0.5699(3) 0.0768(2) 0.0327(9) Uani 1 1 d . . .
N3 N 0.4537(4) 0.7589(3) 0.0839(2) 0.0330(10) Uani 1 1 d . . .
N4 N 0.4039(4) 0.6794(3) 0.0134(3) 0.0333(10) Uani 1 1 d . . .
C1 C 0.8402(6) 0.5487(4) 0.0718(3) 0.0331(11) Uani 1 1 d . . .
H1 H 0.8764 0.4858 0.0340 0.040 Uiso 1 1 calc R . .
C2 C 0.9349(5) 0.6297(4) 0.1287(3) 0.0322(11) Uani 1 1 d . . .
C3 C 1.0919(6) 0.6462(5) 0.1497(3) 0.0397(12) Uani 1 1 d . . .
H3 H 1.1617 0.5938 0.1237 0.048 Uiso 1 1 calc R . .
C4 C 1.1391(6) 0.7404(5) 0.2091(3) 0.0424(13) Uani 1 1 d . . .
H4 H 1.2442 0.7533 0.2247 0.051 Uiso 1 1 calc R . .
C5 C 1.0372(6) 0.8197(5) 0.2484(3) 0.0437(13) Uani 1 1 d . . .
H5 H 1.0758 0.8855 0.2882 0.052 Uiso 1 1 calc R . .
C6 C 0.8846(6) 0.8042(4) 0.2307(3) 0.0374(12) Uani 1 1 d . . .
H6 H 0.8157 0.8564 0.2578 0.045 Uiso 1 1 calc R . .
C7 C 0.8356(5) 0.7060(4) 0.1696(3) 0.0314(11) Uani 1 1 d . . .
C8 C 0.3138(5) 0.7444(4) -0.0445(3) 0.0373(12) Uani 1 1 d . . .
H8 H 0.2672 0.7126 -0.1011 0.045 Uiso 1 1 calc R . .
C9 C 0.2938(6) 0.8690(4) -0.0126(3) 0.0361(12) Uani 1 1 d . . .
C10 C 0.2066(6) 0.9753(5) -0.0437(4) 0.0502(15) Uani 1 1 d . . .
H10 H 0.1424 0.9735 -0.0998 0.060 Uiso 1 1 calc R . .
C11 C 0.2185(7) 1.0800(5) 0.0097(4) 0.0517(15) Uani 1 1 d . . .
H11 H 0.1589 1.1518 -0.0088 0.062 Uiso 1 1 calc R . .
C12 C 0.3168(6) 1.0855(4) 0.0919(4) 0.0518(15) Uani 1 1 d . . .
H12 H 0.3234 1.1615 0.1262 0.062 Uiso 1 1 calc R . .
C13 C 0.4029(6) 0.9845(4) 0.1236(3) 0.0428(13) Uani 1 1 d . . .
H13 H 0.4693 0.9881 0.1788 0.051 Uiso 1 1 calc R . .
C14 C 0.3872(5) 0.8758(4) 0.0702(3) 0.0330(11) Uani 1 1 d . . .
C15 C 0.5494(5) 0.7121(4) 0.1621(3) 0.0320(11) Uani 1 1 d . . .
H15A H 0.4976 0.6422 0.1901 0.038 Uiso 1 1 calc R . .
H15B H 0.5677 0.7803 0.2079 0.038 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
Ni1 N4 2.105(4) . ?
Ni1 N4 2.105(4) 3_665 ?
Ni1 N2 2.107(4) 3_665 ?
Ni1 N2 2.107(4) . ?
Ni1 Cl1 2.4211(12) 3_665 ?
Ni1 Cl1 2.4211(12) . ?
N1 C7 1.374(5) . ?
N1 N2 1.375(5) . ?
N1 C15 1.443(5) . ?
N2 C1 1.316(6) . ?
N3 N4 1.371(5) . ?
N3 C14 1.379(5) . ?
N3 C15 1.441(5) . ?
N4 C8 1.301(5) . ?
C1 C2 1.411(6) . ?
C1 H1 0.9500 . ?
C2 C7 1.390(6) . ?
C2 C3 1.411(6) . ?
C3 C4 1.363(6) . ?
C3 H3 0.9500 . ?
C4 C5 1.412(7) . ?
C4 H4 0.9500 . ?
C5 C6 1.367(6) . ?
C5 H5 0.9500 . ?
C6 C7 1.413(6) . ?
C6 H6 0.9500 . ?
C8 C9 1.421(6) . ?
C8 H8 0.9500 . ?
C9 C14 1.397(6) . ?
C9 C10 1.415(6) . ?
C10 C11 1.359(7) . ?
C10 H10 0.9500 . ?
C11 C12 1.413(7) . ?
C11 H11 0.9500 . ?
C12 C13 1.368(6) . ?
C12 H12 0.9500 . ?
C13 C14 1.394(6) . ?
C13 H13 0.9500 . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?

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
N4 Ni1 N4 180.0 . 3_665 ?
N4 Ni1 N2 92.63(14) . 3_665 ?
N4 Ni1 N2 87.37(14) 3_665 3_665 ?
N4 Ni1 N2 87.37(14) . . ?
N4 Ni1 N2 92.63(14) 3_665 . ?
N2 Ni1 N2 180.00(17) 3_665 . ?
N4 Ni1 Cl1 87.97(11) . 3_665 ?
N4 Ni1 Cl1 92.03(11) 3_665 3_665 ?
N2 Ni1 Cl1 90.65(11) 3_665 3_665 ?
N2 Ni1 Cl1 89.35(11) . 3_665 ?
N4 Ni1 Cl1 92.03(11) . . ?
N4 Ni1 Cl1 87.97(11) 3_665 . ?
N2 Ni1 Cl1 89.35(11) 3_665 . ?
N2 Ni1 Cl1 90.65(11) . . ?
Cl1 Ni1 Cl1 180.00(5) 3_665 . ?
C7 N1 N2 110.5(4) . . ?
C7 N1 C15 129.3(4) . . ?
N2 N1 C15 120.2(4) . . ?
C1 N2 N1 105.6(4) . . ?
C1 N2 Ni1 131.8(3) . . ?
N1 N2 Ni1 122.1(3) . . ?
N4 N3 C14 110.2(4) . . ?
N4 N3 C15 120.3(4) . . ?
C14 N3 C15 129.2(4) . . ?
C8 N4 N3 107.1(4) . . ?
C8 N4 Ni1 130.1(3) . . ?
N3 N4 Ni1 121.8(3) . . ?
N2 C1 C2 112.6(4) . . ?
N2 C1 H1 123.7 . . ?
C2 C1 H1 123.7 . . ?
C7 C2 C1 104.1(4) . . ?
C7 C2 C3 120.1(4) . . ?
C1 C2 C3 135.8(4) . . ?
C4 C3 C2 117.1(4) . . ?
C4 C3 H3 121.4 . . ?
C2 C3 H3 121.4 . . ?
C3 C4 C5 122.3(5) . . ?
C3 C4 H4 118.8 . . ?
C5 C4 H4 118.8 . . ?
C6 C5 C4 121.8(5) . . ?
C6 C5 H5 119.1 . . ?
C4 C5 H5 119.1 . . ?
C5 C6 C7 115.9(5) . . ?
C5 C6 H6 122.0 . . ?
C7 C6 H6 122.0 . . ?
N1 C7 C2 107.3(4) . . ?
N1 C7 C6 130.0(4) . . ?
C2 C7 C6 122.7(4) . . ?
N4 C8 C9 111.5(4) . . ?
N4 C8 H8 124.3 . . ?
C9 C8 H8 124.3 . . ?
C14 C9 C10 119.5(4) . . ?
C14 C9 C8 104.7(4) . . ?
C10 C9 C8 135.9(5) . . ?
C11 C10 C9 117.3(5) . . ?
C11 C10 H10 121.3 . . ?
C9 C10 H10 121.3 . . ?
C10 C11 C12 122.0(5) . . ?
C10 C11 H11 119.0 . . ?
C12 C11 H11 119.0 . . ?
C13 C12 C11 122.0(5) . . ?
C13 C12 H12 119.0 . . ?
C11 C12 H12 119.0 . . ?
C12 C13 C14 115.9(5) . . ?
C12 C13 H13 122.0 . . ?
C14 C13 H13 122.0 . . ?
N3 C14 C13 130.3(5) . . ?
N3 C14 C9 106.5(4) . . ?
C13 C14 C9 123.2(4) . . ?
N3 C15 N1 111.7(4) . . ?
N3 C15 H15A 109.3 . . ?
N1 C15 H15A 109.3 . . ?
N3 C15 H15B 109.3 . . ?
N1 C15 H15B 109.3 . . ?
H15A C15 H15B 107.9 . . ?

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
C7 N1 N2 C1 0.1(5) . . . . ?
C15 N1 N2 C1 -177.6(4) . . . . ?
C7 N1 N2 Ni1 -172.0(3) . . . . ?
C15 N1 N2 Ni1 10.3(5) . . . . ?
N4 Ni1 N2 C1 -143.9(4) . . . . ?
N4 Ni1 N2 C1 36.1(4) 3_665 . . . ?
Cl1 Ni1 N2 C1 -55.9(4) 3_665 . . . ?
Cl1 Ni1 N2 C1 124.1(4) . . . . ?
N4 Ni1 N2 N1 26.0(3) . . . . ?
N4 Ni1 N2 N1 -154.0(3) 3_665 . . . ?
Cl1 Ni1 N2 N1 114.0(3) 3_665 . . . ?
Cl1 Ni1 N2 N1 -66.0(3) . . . . ?
C14 N3 N4 C8 2.3(5) . . . . ?
C15 N3 N4 C8 176.4(4) . . . . ?
C14 N3 N4 Ni1 171.8(3) . . . . ?
C15 N3 N4 Ni1 -14.1(5) . . . . ?
N2 Ni1 N4 C8 -37.3(5) 3_665 . . . ?
N2 Ni1 N4 C8 142.7(5) . . . . ?
Cl1 Ni1 N4 C8 53.3(4) 3_665 . . . ?
Cl1 Ni1 N4 C8 -126.7(4) . . . . ?
N2 Ni1 N4 N3 155.9(3) 3_665 . . . ?
N2 Ni1 N4 N3 -24.1(3) . . . . ?
Cl1 Ni1 N4 N3 -113.6(3) 3_665 . . . ?
Cl1 Ni1 N4 N3 66.4(3) . . . . ?
N1 N2 C1 C2 0.4(5) . . . . ?
Ni1 N2 C1 C2 171.5(3) . . . . ?
N2 C1 C2 C7 -0.8(5) . . . . ?
N2 C1 C2 C3 179.1(5) . . . . ?
C7 C2 C3 C4 -1.5(7) . . . . ?
C1 C2 C3 C4 178.7(5) . . . . ?
C2 C3 C4 C5 -0.3(7) . . . . ?
C3 C4 C5 C6 1.6(8) . . . . ?
C4 C5 C6 C7 -1.1(7) . . . . ?
N2 N1 C7 C2 -0.6(5) . . . . ?
C15 N1 C7 C2 176.8(4) . . . . ?
N2 N1 C7 C6 178.2(4) . . . . ?
C15 N1 C7 C6 -4.4(8) . . . . ?
C1 C2 C7 N1 0.8(5) . . . . ?
C3 C2 C7 N1 -179.1(4) . . . . ?
C1 C2 C7 C6 -178.1(4) . . . . ?
C3 C2 C7 C6 2.0(7) . . . . ?
C5 C6 C7 N1 -179.3(4) . . . . ?
C5 C6 C7 C2 -0.6(7) . . . . ?
N3 N4 C8 C9 -3.0(6) . . . . ?
Ni1 N4 C8 C9 -171.3(3) . . . . ?
N4 C8 C9 C14 2.6(6) . . . . ?
N4 C8 C9 C10 -176.6(6) . . . . ?
C14 C9 C10 C11 -0.2(8) . . . . ?
C8 C9 C10 C11 178.9(6) . . . . ?
C9 C10 C11 C12 1.9(8) . . . . ?
C10 C11 C12 C13 -1.7(9) . . . . ?
C11 C12 C13 C14 -0.2(8) . . . . ?
N4 N3 C14 C13 179.5(5) . . . . ?
C15 N3 C14 C13 6.0(8) . . . . ?
N4 N3 C14 C9 -0.7(5) . . . . ?
C15 N3 C14 C9 -174.1(4) . . . . ?
C12 C13 C14 N3 -178.2(5) . . . . ?
C12 C13 C14 C9 2.0(8) . . . . ?
C10 C9 C14 N3 178.3(4) . . . . ?
C8 C9 C14 N3 -1.1(5) . . . . ?
C10 C9 C14 C13 -1.8(8) . . . . ?
C8 C9 C14 C13 178.8(5) . . . . ?
N4 N3 C15 N1 63.3(5) . . . . ?
C14 N3 C15 N1 -123.8(5) . . . . ?
C7 N1 C15 N3 121.9(5) . . . . ?
N2 N1 C15 N3 -60.9(5) . . . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        25.25
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.385
_refine_diff_density_min         -0.385
_refine_diff_density_rms         0.091
####################################################################### 
# 
# 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_6
_database_code_depnum_ccdc_archive 'CCDC 1435380'
_audit_update_record             
;
2015-11-05 deposited with the CCDC.
2016-01-08 downloaded from the CCDC.
;


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C30 H24 N8 Pd, 2(Cl)'
_chemical_formula_sum            'C30 H24 Cl2 N8 Pd'
_chemical_formula_weight         673.87

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_H-M   'C 2/c'
_symmetry_space_group_name_Hall  '-C 2yc'

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                   29.0224(14)
_cell_length_b                   12.4346(8)
_cell_length_c                   21.629(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 124.944(2)
_cell_angle_gamma                90.00
_cell_volume                     6398.3(8)
_cell_formula_units_Z            8
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    4044
_cell_measurement_theta_min      2.30
_cell_measurement_theta_max      21.44

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.399
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2720
_exptl_absorpt_coefficient_mu    0.779
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8767
_exptl_absorpt_correction_T_max  0.9403
_exptl_absorpt_process_details   
;
program SADABS, Bruker (2001).
;
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  
;
 Bruker-Nonius X8kappa APEX II CCD area detector
;
_diffrn_measurement_method       'phi and omega scans with narrow frames'
_diffrn_detector_area_resol_mean 8.26
_diffrn_standards_decay_%        0
_diffrn_reflns_number            37724
_diffrn_reflns_av_R_equivalents  0.0911
_diffrn_reflns_av_sigmaI/netI    0.0675
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_h_max       34
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.85
_diffrn_reflns_theta_max         25.25
_reflns_number_total             5742
_reflns_number_gt                4402
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 Software Suite (Bruker, 2007)'
_computing_cell_refinement       'APEX2 Software Suite (Bruker, 2007)'
_computing_data_reduction        'APEX2 Software Suite (Bruker, 2007)'
_computing_structure_solution    'SIR2002 (Burla et al., 2003)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL and publCIF (Westrip, 2010)'

_refine_special_details          SQUEEZE

_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)+(0.0655P)²+9.2623P] 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         5742
_refine_ls_number_parameters     370
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0656
_refine_ls_R_factor_gt           0.0490
_refine_ls_wR_factor_ref         0.1329
_refine_ls_wR_factor_gt          0.1261
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_restrained_S_all      1.044
_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 0.291938(13) 0.14258(3) 0.205110(18) 0.01889(12) Uani 1 1 d . . .
N1 N 0.34131(15) 0.0301(3) 0.2812(2) 0.0245(8) Uani 1 1 d . . .
N2 N 0.34215(15) -0.0720(3) 0.2574(2) 0.0263(8) Uani 1 1 d . . .
N3 N 0.23599(15) 0.0260(3) 0.1445(2) 0.0244(8) Uani 1 1 d . . .
N4 N 0.25347(15) -0.0722(3) 0.1380(2) 0.0244(8) Uani 1 1 d . . .
N5 N 0.34968(14) 0.2594(3) 0.26381(19) 0.0215(7) Uani 1 1 d . . .
N6 N 0.33176(14) 0.3620(3) 0.26036(19) 0.0207(7) Uani 1 1 d . . .
N7 N 0.24228(14) 0.2531(3) 0.12618(18) 0.0200(7) Uani 1 1 d . . .
N8 N 0.24055(14) 0.3555(3) 0.1478(2) 0.0203(7) Uani 1 1 d . . .
C1 C 0.37447(19) -0.1386(4) 0.3144(3) 0.0299(10) Uani 1 1 d . . .
H1 H 0.3814 -0.2122 0.3106 0.036 Uiso 1 1 calc R . .
C2 C 0.39624(17) -0.0806(4) 0.3805(3) 0.0281(10) Uani 1 1 d . . .
C3 C 0.4329(2) -0.1030(4) 0.4596(3) 0.0374(12) Uani 1 1 d . . .
H3 H 0.4488 -0.1726 0.4768 0.045 Uiso 1 1 calc R . .
C4 C 0.4447(2) -0.0237(4) 0.5092(3) 0.0393(12) Uani 1 1 d . . .
H4 H 0.4688 -0.0384 0.5618 0.047 Uiso 1 1 calc R . .
C5 C 0.4220(2) 0.0799(4) 0.4851(3) 0.0357(11) Uani 1 1 d . . .
H5 H 0.4316 0.1334 0.5220 0.043 Uiso 1 1 calc R . .
C6 C 0.38642(19) 0.1069(4) 0.4101(3) 0.0302(10) Uani 1 1 d . . .
H6 H 0.3711 0.1772 0.3946 0.036 Uiso 1 1 calc R . .
C7 C 0.37382(18) 0.0255(3) 0.3574(2) 0.0242(9) Uani 1 1 d . . .
C8 C 0.2105(2) -0.1388(4) 0.0924(3) 0.0292(10) Uani 1 1 d . . .
H8 H 0.2129 -0.2103 0.0791 0.035 Uiso 1 1 calc R . .
C9 C 0.16183(19) -0.0824(4) 0.0688(2) 0.0288(10) Uani 1 1 d . . .
C10 C 0.1030(2) -0.1081(4) 0.0195(3) 0.0359(11) Uani 1 1 d . . .
H10 H 0.0906 -0.1762 -0.0045 0.043 Uiso 1 1 calc R . .
C11 C 0.0662(2) -0.0314(4) 0.0089(3) 0.0385(12) Uani 1 1 d . . .
H11 H 0.0271 -0.0459 -0.0236 0.046 Uiso 1 1 calc R . .
C12 C 0.08438(19) 0.0703(4) 0.0447(3) 0.0355(11) Uani 1 1 d . . .
H12 H 0.0568 0.1212 0.0359 0.043 Uiso 1 1 calc R . .
C13 C 0.13963(19) 0.0980(4) 0.0913(3) 0.0280(10) Uani 1 1 d . . .
H13 H 0.1510 0.1666 0.1147 0.034 Uiso 1 1 calc R . .
C14 C 0.17942(17) 0.0196(3) 0.1031(2) 0.0221(9) Uani 1 1 d . . .
C15 C 0.31403(19) -0.0916(4) 0.1769(3) 0.0312(10) Uani 1 1 d . . .
H15A H 0.3205 -0.1668 0.1686 0.037 Uiso 1 1 calc R . .
H15B H 0.3294 -0.0431 0.1566 0.037 Uiso 1 1 calc R . .
C16 C 0.37240(18) 0.4338(4) 0.2842(2) 0.0267(10) Uani 1 1 d . . .
H16 H 0.3690 0.5094 0.2864 0.032 Uiso 1 1 calc R . .
C17 C 0.42119(18) 0.3777(4) 0.3056(3) 0.0270(10) Uani 1 1 d . . .
C18 C 0.47661(19) 0.4080(4) 0.3329(3) 0.0381(12) Uani 1 1 d . . .
H18 H 0.4878 0.4814 0.3419 0.046 Uiso 1 1 calc R . .
C19 C 0.5130(2) 0.3299(5) 0.3457(3) 0.0422(13) Uani 1 1 d . . .
H19 H 0.5506 0.3488 0.3643 0.051 Uiso 1 1 calc R . .
C20 C 0.49734(19) 0.2214(4) 0.3325(3) 0.0354(11) Uani 1 1 d . . .
H20 H 0.5249 0.1692 0.3431 0.042 Uiso 1 1 calc R . .
C21 C 0.44369(18) 0.1874(4) 0.3048(2) 0.0280(10) Uani 1 1 d . . .
H21 H 0.4333 0.1137 0.2953 0.034 Uiso 1 1 calc R . .
C22 C 0.40521(17) 0.2687(4) 0.2913(2) 0.0216(9) Uani 1 1 d . . .
C23 C 0.20939(17) 0.4209(4) 0.0889(2) 0.0242(9) Uani 1 1 d . . .
H23 H 0.2027 0.4952 0.0910 0.029 Uiso 1 1 calc R . .
C24 C 0.18860(17) 0.3607(4) 0.0245(2) 0.0231(9) Uani 1 1 d . . .
C25 C 0.15355(18) 0.3848(4) -0.0536(3) 0.0305(11) Uani 1 1 d . . .
H25 H 0.1381 0.4545 -0.0712 0.037 Uiso 1 1 calc R . .
C26 C 0.14289(19) 0.3030(5) -0.1029(3) 0.0352(11) Uani 1 1 d . . .
H26 H 0.1192 0.3165 -0.1556 0.042 Uiso 1 1 calc R . .
C27 C 0.16649(19) 0.1978(4) -0.0769(3) 0.0312(11) Uani 1 1 d . . .
H27 H 0.1588 0.1440 -0.1128 0.037 Uiso 1 1 calc R . .
C28 C 0.19981(18) 0.1728(4) -0.0018(2) 0.0256(10) Uani 1 1 d . . .
H28 H 0.2151 0.1028 0.0151 0.031 Uiso 1 1 calc R . .
C29 C 0.21048(16) 0.2559(4) 0.0496(2) 0.0215(9) Uani 1 1 d . . .
C30 C 0.27321(17) 0.3798(3) 0.2286(2) 0.0204(9) Uani 1 1 d . . .
H30A H 0.2671 0.4556 0.2363 0.025 Uiso 1 1 calc R . .
H30B H 0.2610 0.3328 0.2537 0.025 Uiso 1 1 calc R . .
Cl1 Cl 0.22520(5) 0.15790(9) 0.28682(7) 0.0299(3) Uani 1 1 d . . .
Cl2 Cl 0.02008(10) 0.2070(2) 0.15856(13) 0.1087(8) Uani 1 1 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 N1 2.004(4) . ?
Pd1 N3 2.005(4) . ?
Pd1 N7 2.016(3) . ?
Pd1 N5 2.023(3) . ?
N1 C7 1.353(6) . ?
N1 N2 1.375(5) . ?
N2 C1 1.327(6) . ?
N2 C15 1.459(6) . ?
N3 C14 1.349(5) . ?
N3 N4 1.360(5) . ?
N4 C8 1.343(6) . ?
N4 C15 1.470(6) . ?
N5 N6 1.363(5) . ?
N5 C22 1.366(5) . ?
N6 C16 1.325(5) . ?
N6 C30 1.439(5) . ?
N7 C29 1.358(5) . ?
N7 N8 1.367(5) . ?
N8 C23 1.335(5) . ?
N8 C30 1.464(5) . ?
C1 C2 1.389(7) . ?
C1 H1 0.9500 . ?
C2 C7 1.429(6) . ?
C2 C3 1.432(7) . ?
C3 C4 1.351(7) . ?
C3 H3 0.9500 . ?
C4 C5 1.404(7) . ?
C4 H4 0.9500 . ?
C5 C6 1.375(7) . ?
C5 H5 0.9500 . ?
C6 C7 1.408(6) . ?
C6 H6 0.9500 . ?
C8 C9 1.386(7) . ?
C8 H8 0.9500 . ?
C9 C14 1.409(6) . ?
C9 C10 1.438(7) . ?
C10 C11 1.349(7) . ?
C10 H10 0.9500 . ?
C11 C12 1.418(7) . ?
C11 H11 0.9500 . ?
C12 C13 1.361(6) . ?
C12 H12 0.9500 . ?
C13 C14 1.418(6) . ?
C13 H13 0.9500 . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C17 1.398(6) . ?
C16 H16 0.9500 . ?
C17 C22 1.408(6) . ?
C17 C18 1.411(6) . ?
C18 C19 1.342(7) . ?
C18 H18 0.9500 . ?
C19 C20 1.400(7) . ?
C19 H19 0.9500 . ?
C20 C21 1.376(6) . ?
C20 H20 0.9500 . ?
C21 C22 1.408(6) . ?
C21 H21 0.9500 . ?
C23 C24 1.379(6) . ?
C23 H23 0.9500 . ?
C24 C29 1.415(6) . ?
C24 C25 1.418(6) . ?
C25 C26 1.374(7) . ?
C25 H25 0.9500 . ?
C26 C27 1.433(7) . ?
C26 H26 0.9500 . ?
C27 C28 1.368(6) . ?
C27 H27 0.9500 . ?
C28 C29 1.415(6) . ?
C28 H28 0.9500 . ?
C30 H30A 0.9900 . ?
C30 H30B 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 Pd1 N3 87.84(15) . . ?
N1 Pd1 N7 178.26(14) . . ?
N3 Pd1 N7 91.22(14) . . ?
N1 Pd1 N5 92.30(14) . . ?
N3 Pd1 N5 177.71(14) . . ?
N7 Pd1 N5 88.58(14) . . ?
C7 N1 N2 105.5(3) . . ?
C7 N1 Pd1 134.6(3) . . ?
N2 N1 Pd1 119.6(3) . . ?
C1 N2 N1 112.5(4) . . ?
C1 N2 C15 128.2(4) . . ?
N1 N2 C15 118.9(4) . . ?
C14 N3 N4 105.3(3) . . ?
C14 N3 Pd1 134.3(3) . . ?
N4 N3 Pd1 120.4(3) . . ?
C8 N4 N3 112.6(4) . . ?
C8 N4 C15 128.5(4) . . ?
N3 N4 C15 118.9(3) . . ?
N6 N5 C22 105.2(3) . . ?
N6 N5 Pd1 119.0(2) . . ?
C22 N5 Pd1 132.9(3) . . ?
C16 N6 N5 112.5(4) . . ?
C16 N6 C30 128.8(4) . . ?
N5 N6 C30 118.6(3) . . ?
C29 N7 N8 105.2(3) . . ?
C29 N7 Pd1 135.0(3) . . ?
N8 N7 Pd1 119.6(2) . . ?
C23 N8 N7 112.2(3) . . ?
C23 N8 C30 129.4(4) . . ?
N7 N8 C30 118.4(3) . . ?
N2 C1 C2 107.1(4) . . ?
N2 C1 H1 126.4 . . ?
C2 C1 H1 126.4 . . ?
C1 C2 C7 105.8(4) . . ?
C1 C2 C3 135.9(4) . . ?
C7 C2 C3 118.3(4) . . ?
C4 C3 C2 119.0(5) . . ?
C4 C3 H3 120.5 . . ?
C2 C3 H3 120.5 . . ?
C3 C4 C5 121.5(5) . . ?
C3 C4 H4 119.2 . . ?
C5 C4 H4 119.2 . . ?
C6 C5 C4 122.6(5) . . ?
C6 C5 H5 118.7 . . ?
C4 C5 H5 118.7 . . ?
C5 C6 C7 116.8(5) . . ?
C5 C6 H6 121.6 . . ?
C7 C6 H6 121.6 . . ?
N1 C7 C6 129.2(4) . . ?
N1 C7 C2 109.0(4) . . ?
C6 C7 C2 121.8(4) . . ?
N4 C8 C9 106.3(4) . . ?
N4 C8 H8 126.8 . . ?
C9 C8 H8 126.8 . . ?
C8 C9 C14 106.0(4) . . ?
C8 C9 C10 133.4(5) . . ?
C14 C9 C10 120.6(4) . . ?
C11 C10 C9 117.2(5) . . ?
C11 C10 H10 121.4 . . ?
C9 C10 H10 121.4 . . ?
C10 C11 C12 121.8(5) . . ?
C10 C11 H11 119.1 . . ?
C12 C11 H11 119.1 . . ?
C13 C12 C11 122.8(5) . . ?
C13 C12 H12 118.6 . . ?
C11 C12 H12 118.6 . . ?
C12 C13 C14 116.9(4) . . ?
C12 C13 H13 121.6 . . ?
C14 C13 H13 121.6 . . ?
N3 C14 C9 109.8(4) . . ?
N3 C14 C13 129.5(4) . . ?
C9 C14 C13 120.8(4) . . ?
N2 C15 N4 108.9(4) . . ?
N2 C15 H15A 109.9 . . ?
N4 C15 H15A 109.9 . . ?
N2 C15 H15B 109.9 . . ?
N4 C15 H15B 109.9 . . ?
H15A C15 H15B 108.3 . . ?
N6 C16 C17 107.5(4) . . ?
N6 C16 H16 126.3 . . ?
C17 C16 H16 126.3 . . ?
C16 C17 C22 105.3(4) . . ?
C16 C17 C18 134.5(5) . . ?
C22 C17 C18 120.2(4) . . ?
C19 C18 C17 117.9(5) . . ?
C19 C18 H18 121.1 . . ?
C17 C18 H18 121.1 . . ?
C18 C19 C20 122.0(5) . . ?
C18 C19 H19 119.0 . . ?
C20 C19 H19 119.0 . . ?
C21 C20 C19 122.7(5) . . ?
C21 C20 H20 118.7 . . ?
C19 C20 H20 118.7 . . ?
C20 C21 C22 115.8(5) . . ?
C20 C21 H21 122.1 . . ?
C22 C21 H21 122.1 . . ?
N5 C22 C21 128.9(4) . . ?
N5 C22 C17 109.6(4) . . ?
C21 C22 C17 121.5(4) . . ?
N8 C23 C24 107.4(4) . . ?
N8 C23 H23 126.3 . . ?
C24 C23 H23 126.3 . . ?
C23 C24 C29 105.8(4) . . ?
C23 C24 C25 133.6(4) . . ?
C29 C24 C25 120.6(4) . . ?
C26 C25 C24 117.2(4) . . ?
C26 C25 H25 121.4 . . ?
C24 C25 H25 121.4 . . ?
C25 C26 C27 121.8(4) . . ?
C25 C26 H26 119.1 . . ?
C27 C26 H26 119.1 . . ?
C28 C27 C26 121.8(4) . . ?
C28 C27 H27 119.1 . . ?
C26 C27 H27 119.1 . . ?
C27 C28 C29 117.0(4) . . ?
C27 C28 H28 121.5 . . ?
C29 C28 H28 121.5 . . ?
N7 C29 C24 109.4(4) . . ?
N7 C29 C28 129.0(4) . . ?
C24 C29 C28 121.5(4) . . ?
N6 C30 N8 108.6(3) . . ?
N6 C30 H30A 110.0 . . ?
N8 C30 H30A 110.0 . . ?
N6 C30 H30B 110.0 . . ?
N8 C30 H30B 110.0 . . ?
H30A C30 H30B 108.4 . . ?

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
N3 Pd1 N1 C7 -138.2(4) . . . . ?
N5 Pd1 N1 C7 44.1(4) . . . . ?
N3 Pd1 N1 N2 34.9(3) . . . . ?
N5 Pd1 N1 N2 -142.8(3) . . . . ?
C7 N1 N2 C1 -1.7(5) . . . . ?
Pd1 N1 N2 C1 -176.6(3) . . . . ?
C7 N1 N2 C15 -175.4(4) . . . . ?
Pd1 N1 N2 C15 9.6(5) . . . . ?
N1 Pd1 N3 C14 141.1(4) . . . . ?
N7 Pd1 N3 C14 -40.4(4) . . . . ?
N1 Pd1 N3 N4 -40.5(3) . . . . ?
N7 Pd1 N3 N4 138.1(3) . . . . ?
C14 N3 N4 C8 2.0(5) . . . . ?
Pd1 N3 N4 C8 -176.8(3) . . . . ?
C14 N3 N4 C15 179.7(4) . . . . ?
Pd1 N3 N4 C15 0.9(5) . . . . ?
N1 Pd1 N5 N6 -149.0(3) . . . . ?
N7 Pd1 N5 N6 32.5(3) . . . . ?
N1 Pd1 N5 C22 53.4(4) . . . . ?
N7 Pd1 N5 C22 -125.1(4) . . . . ?
C22 N5 N6 C16 -0.4(5) . . . . ?
Pd1 N5 N6 C16 -163.5(3) . . . . ?
C22 N5 N6 C30 176.0(3) . . . . ?
Pd1 N5 N6 C30 12.9(5) . . . . ?
N3 Pd1 N7 C29 -42.2(4) . . . . ?
N5 Pd1 N7 C29 135.5(4) . . . . ?
N3 Pd1 N7 N8 145.0(3) . . . . ?
N5 Pd1 N7 N8 -37.3(3) . . . . ?
C29 N7 N8 C23 0.2(4) . . . . ?
Pd1 N7 N8 C23 174.9(3) . . . . ?
C29 N7 N8 C30 -177.6(3) . . . . ?
Pd1 N7 N8 C30 -2.8(4) . . . . ?
N1 N2 C1 C2 1.0(5) . . . . ?
C15 N2 C1 C2 174.0(4) . . . . ?
N2 C1 C2 C7 0.2(5) . . . . ?
N2 C1 C2 C3 180.0(5) . . . . ?
C1 C2 C3 C4 -179.3(5) . . . . ?
C7 C2 C3 C4 0.5(7) . . . . ?
C2 C3 C4 C5 -0.4(7) . . . . ?
C3 C4 C5 C6 0.6(8) . . . . ?
C4 C5 C6 C7 -0.7(7) . . . . ?
N2 N1 C7 C6 -178.7(4) . . . . ?
Pd1 N1 C7 C6 -4.9(7) . . . . ?
N2 N1 C7 C2 1.7(4) . . . . ?
Pd1 N1 C7 C2 175.6(3) . . . . ?
C5 C6 C7 N1 -178.7(4) . . . . ?
C5 C6 C7 C2 0.8(7) . . . . ?
C1 C2 C7 N1 -1.2(5) . . . . ?
C3 C2 C7 N1 178.9(4) . . . . ?
C1 C2 C7 C6 179.2(4) . . . . ?
C3 C2 C7 C6 -0.7(6) . . . . ?
N3 N4 C8 C9 -1.3(5) . . . . ?
C15 N4 C8 C9 -178.8(4) . . . . ?
N4 C8 C9 C14 0.1(5) . . . . ?
N4 C8 C9 C10 179.1(5) . . . . ?
C8 C9 C10 C11 -179.7(5) . . . . ?
C14 C9 C10 C11 -0.8(7) . . . . ?
C9 C10 C11 C12 -0.3(7) . . . . ?
C10 C11 C12 C13 0.9(8) . . . . ?
C11 C12 C13 C14 -0.2(7) . . . . ?
N4 N3 C14 C9 -1.9(5) . . . . ?
Pd1 N3 C14 C9 176.7(3) . . . . ?
N4 N3 C14 C13 178.7(4) . . . . ?
Pd1 N3 C14 C13 -2.7(7) . . . . ?
C8 C9 C14 N3 1.1(5) . . . . ?
C10 C9 C14 N3 -178.0(4) . . . . ?
C8 C9 C14 C13 -179.4(4) . . . . ?
C10 C9 C14 C13 1.5(7) . . . . ?
C12 C13 C14 N3 178.4(4) . . . . ?
C12 C13 C14 C9 -0.9(6) . . . . ?
C1 N2 C15 N4 123.6(5) . . . . ?
N1 N2 C15 N4 -63.8(5) . . . . ?
C8 N4 C15 N2 -125.1(4) . . . . ?
N3 N4 C15 N2 57.6(5) . . . . ?
N5 N6 C16 C17 -0.2(5) . . . . ?
C30 N6 C16 C17 -176.1(4) . . . . ?
N6 C16 C17 C22 0.7(5) . . . . ?
N6 C16 C17 C18 177.9(5) . . . . ?
C16 C17 C18 C19 -178.0(5) . . . . ?
C22 C17 C18 C19 -1.2(7) . . . . ?
C17 C18 C19 C20 0.3(8) . . . . ?
C18 C19 C20 C21 0.8(8) . . . . ?
C19 C20 C21 C22 -0.9(7) . . . . ?
N6 N5 C22 C21 -178.8(4) . . . . ?
Pd1 N5 C22 C21 -19.1(7) . . . . ?
N6 N5 C22 C17 0.8(4) . . . . ?
Pd1 N5 C22 C17 160.6(3) . . . . ?
C20 C21 C22 N5 179.6(4) . . . . ?
C20 C21 C22 C17 0.0(6) . . . . ?
C16 C17 C22 N5 -0.9(5) . . . . ?
C18 C17 C22 N5 -178.6(4) . . . . ?
C16 C17 C22 C21 178.7(4) . . . . ?
C18 C17 C22 C21 1.0(7) . . . . ?
N7 N8 C23 C24 0.5(5) . . . . ?
C30 N8 C23 C24 177.9(4) . . . . ?
N8 C23 C24 C29 -1.0(4) . . . . ?
N8 C23 C24 C25 179.9(4) . . . . ?
C23 C24 C25 C26 177.9(4) . . . . ?
C29 C24 C25 C26 -1.1(6) . . . . ?
C24 C25 C26 C27 -0.6(6) . . . . ?
C25 C26 C27 C28 1.5(7) . . . . ?
C26 C27 C28 C29 -0.5(6) . . . . ?
N8 N7 C29 C24 -0.8(4) . . . . ?
Pd1 N7 C29 C24 -174.3(3) . . . . ?
N8 N7 C29 C28 177.3(4) . . . . ?
Pd1 N7 C29 C28 3.7(7) . . . . ?
C23 C24 C29 N7 1.1(4) . . . . ?
C25 C24 C29 N7 -179.7(4) . . . . ?
C23 C24 C29 C28 -177.1(4) . . . . ?
C25 C24 C29 C28 2.1(6) . . . . ?
C27 C28 C29 N7 -179.1(4) . . . . ?
C27 C28 C29 C24 -1.2(6) . . . . ?
C16 N6 C30 N8 107.9(5) . . . . ?
N5 N6 C30 N8 -67.8(4) . . . . ?
C23 N8 C30 N6 -115.6(4) . . . . ?
N7 N8 C30 N6 61.6(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        25.25
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         1.238
_refine_diff_density_min         -1.141
_refine_diff_density_rms         0.106

loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.077 0.250 0.327 613 190 ' '
2 0.076 -0.250 0.826 613 190 ' '
_platon_squeeze_details          
;
;
####################################################################### 
# 
# 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_7
_database_code_depnum_ccdc_archive 'CCDC 1435381'
_audit_update_record             
;
2015-11-05 deposited with the CCDC.
2016-01-08 downloaded from the CCDC.
;


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H18 N4 O4 Pd'
_chemical_formula_sum            'C19 H18 N4 O4 Pd'
_chemical_formula_weight         472.77

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           Triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.034(3)
_cell_length_b                   10.625(3)
_cell_length_c                   10.670(3)
_cell_angle_alpha                85.207(9)
_cell_angle_beta                 76.725(10)
_cell_angle_gamma                89.439(9)
_cell_volume                     1103.2(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    4538
_cell_measurement_theta_min      2.82
_cell_measurement_theta_max      22.70

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.423
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             476
_exptl_absorpt_coefficient_mu    0.870
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9009
_exptl_absorpt_correction_T_max  0.9568
_exptl_absorpt_process_details   
;
program SADABS, Bruker (2001).
;
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  
;
 Bruker-Nonius X8kappa APEX II CCD area detector
;
_diffrn_measurement_method       'phi and omega scans with narrow frames'
_diffrn_detector_area_resol_mean 8.26
_diffrn_standards_decay_%        0
_diffrn_reflns_number            18721
_diffrn_reflns_av_R_equivalents  0.0487
_diffrn_reflns_av_sigmaI/netI    0.0435
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         1.92
_diffrn_reflns_theta_max         25.25
_reflns_number_total             3981
_reflns_number_gt                3421
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 Software Suite (Bruker, 2007)'
_computing_cell_refinement       'APEX2 Software Suite (Bruker, 2007)'
_computing_data_reduction        'APEX2 Software Suite (Bruker, 2007)'
_computing_structure_solution    'SIR2002 (Burla et al., 2003)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL and publCIF (Westrip, 2010)'

_refine_special_details          SQUEEZE

_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)+(0.0516P)²+1.0788P] 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         3981
_refine_ls_number_parameters     255
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0452
_refine_ls_R_factor_gt           0.0382
_refine_ls_wR_factor_ref         0.1001
_refine_ls_wR_factor_gt          0.0978
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_restrained_S_all      1.025
_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 0.33667(3) 0.30927(3) 0.55226(3) 0.03005(12) Uani 1 1 d . . .
O1 O 0.1889(3) 0.3543(3) 0.7055(3) 0.0489(7) Uani 1 1 d . . .
O2 O 0.1460(4) 0.5261(3) 0.5950(4) 0.0704(10) Uani 1 1 d . . .
O3 O 0.4769(3) 0.3904(2) 0.6252(3) 0.0380(6) Uani 1 1 d . . .
O4 O 0.5674(3) 0.2049(3) 0.6696(3) 0.0508(8) Uani 1 1 d . . .
N1 N 0.4692(3) 0.1430(3) 0.3560(3) 0.0292(6) Uani 1 1 d . . .
N2 N 0.4801(3) 0.2588(3) 0.4012(3) 0.0308(7) Uani 1 1 d . . .
N3 N 0.2283(3) 0.1161(3) 0.4232(3) 0.0284(6) Uani 1 1 d . . .
N4 N 0.1972(3) 0.2299(3) 0.4737(3) 0.0304(7) Uani 1 1 d . . .
C1 C 0.5744(4) 0.3261(4) 0.3149(4) 0.0323(8) Uani 1 1 d . . .
H1 H 0.6033 0.4090 0.3241 0.039 Uiso 1 1 calc R . .
C2 C 0.6254(4) 0.2563(3) 0.2077(4) 0.0322(8) Uani 1 1 d . . .
C3 C 0.7250(4) 0.2790(4) 0.0906(4) 0.0423(9) Uani 1 1 d . . .
H3 H 0.7769 0.3553 0.0711 0.051 Uiso 1 1 calc R . .
C4 C 0.7438(5) 0.1861(4) 0.0061(4) 0.0473(10) Uani 1 1 d . . .
H4 H 0.8089 0.1995 -0.0740 0.057 Uiso 1 1 calc R . .
C5 C 0.6702(4) 0.0726(4) 0.0345(4) 0.0449(10) Uani 1 1 d . . .
H5 H 0.6865 0.0116 -0.0273 0.054 Uiso 1 1 calc R . .
C6 C 0.5746(4) 0.0457(4) 0.1490(4) 0.0368(9) Uani 1 1 d . . .
H6 H 0.5257 -0.0322 0.1681 0.044 Uiso 1 1 calc R . .
C7 C 0.5540(3) 0.1404(3) 0.2356(3) 0.0272(7) Uani 1 1 d . . .
C8 C 0.0780(4) 0.2649(4) 0.4523(4) 0.0327(8) Uani 1 1 d . . .
H8 H 0.0332 0.3413 0.4764 0.039 Uiso 1 1 calc R . .
C9 C 0.0262(4) 0.1720(3) 0.3881(3) 0.0293(8) Uani 1 1 d . . .
C10 C -0.0938(4) 0.1566(4) 0.3451(4) 0.0393(9) Uani 1 1 d . . .
H10 H -0.1632 0.2188 0.3562 0.047 Uiso 1 1 calc R . .
C11 C -0.1083(4) 0.0498(4) 0.2867(4) 0.0402(9) Uani 1 1 d . . .
H11 H -0.1886 0.0386 0.2558 0.048 Uiso 1 1 calc R . .
C12 C -0.0082(4) -0.0434(4) 0.2712(4) 0.0360(9) Uani 1 1 d . . .
H12 H -0.0236 -0.1171 0.2317 0.043 Uiso 1 1 calc R . .
C13 C 0.1110(4) -0.0324(4) 0.3108(3) 0.0313(8) Uani 1 1 d . . .
H13 H 0.1796 -0.0954 0.2988 0.038 Uiso 1 1 calc R . .
C14 C 0.1257(4) 0.0780(3) 0.3702(3) 0.0283(7) Uani 1 1 d . . .
C15 C 0.3589(3) 0.0602(3) 0.4277(4) 0.0285(7) Uani 1 1 d . . .
H15A H 0.3660 -0.0224 0.3900 0.034 Uiso 1 1 calc R . .
H15B H 0.3664 0.0455 0.5186 0.034 Uiso 1 1 calc R . .
C16 C 0.1264(4) 0.4514(4) 0.6916(4) 0.0412(10) Uani 1 1 d . . .
C17 C 0.0127(5) 0.4802(6) 0.8088(5) 0.0682(15) Uani 1 1 d . . .
H17A H 0.0210 0.4236 0.8839 0.102 Uiso 1 1 calc R . .
H17B H -0.0768 0.4674 0.7896 0.102 Uiso 1 1 calc R . .
H17C H 0.0216 0.5681 0.8277 0.102 Uiso 1 1 calc R . .
C18 C 0.5674(4) 0.3197(4) 0.6640(4) 0.0357(9) Uani 1 1 d . . .
C19 C 0.6773(5) 0.3929(4) 0.7036(5) 0.0548(12) Uani 1 1 d . . .
H19A H 0.6581 0.4834 0.6952 0.082 Uiso 1 1 calc R . .
H19B H 0.7666 0.3761 0.6477 0.082 Uiso 1 1 calc R . .
H19C H 0.6784 0.3666 0.7936 0.082 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 O3 1.992(3) . ?
Pd1 N2 2.005(3) . ?
Pd1 N4 2.013(3) . ?
Pd1 O1 2.026(3) . ?
O1 C16 1.219(5) . ?
O2 C16 1.226(6) . ?
O3 C18 1.291(5) . ?
O4 C18 1.216(5) . ?
N1 C7 1.370(5) . ?
N1 N2 1.372(4) . ?
N1 C15 1.450(4) . ?
N2 C1 1.326(5) . ?
N3 C14 1.362(5) . ?
N3 N4 1.369(4) . ?
N3 C15 1.443(4) . ?
N4 C8 1.313(5) . ?
C1 C2 1.410(5) . ?
C1 H1 0.9500 . ?
C2 C7 1.406(5) . ?
C2 C3 1.414(6) . ?
C3 C4 1.375(6) . ?
C3 H3 0.9500 . ?
C4 C5 1.394(6) . ?
C4 H4 0.9500 . ?
C5 C6 1.379(6) . ?
C5 H5 0.9500 . ?
C6 C7 1.404(5) . ?
C6 H6 0.9500 . ?
C8 C9 1.414(5) . ?
C8 H8 0.9500 . ?
C9 C14 1.399(5) . ?
C9 C10 1.399(5) . ?
C10 C11 1.363(6) . ?
C10 H10 0.9500 . ?
C11 C12 1.396(6) . ?
C11 H11 0.9500 . ?
C12 C13 1.366(5) . ?
C12 H12 0.9500 . ?
C13 C14 1.404(5) . ?
C13 H13 0.9500 . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C17 1.536(6) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 C19 1.512(6) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O3 Pd1 N2 91.47(12) . . ?
O3 Pd1 N4 178.39(12) . . ?
N2 Pd1 N4 87.47(12) . . ?
O3 Pd1 O1 89.94(12) . . ?
N2 Pd1 O1 178.02(12) . . ?
N4 Pd1 O1 91.15(12) . . ?
C16 O1 Pd1 116.8(3) . . ?
C18 O3 Pd1 118.5(2) . . ?
C7 N1 N2 109.3(3) . . ?
C7 N1 C15 132.3(3) . . ?
N2 N1 C15 117.2(3) . . ?
C1 N2 N1 108.1(3) . . ?
C1 N2 Pd1 131.4(2) . . ?
N1 N2 Pd1 119.0(2) . . ?
C14 N3 N4 110.3(3) . . ?
C14 N3 C15 131.0(3) . . ?
N4 N3 C15 118.6(3) . . ?
C8 N4 N3 107.6(3) . . ?
C8 N4 Pd1 134.4(3) . . ?
N3 N4 Pd1 117.8(2) . . ?
N2 C1 C2 109.9(3) . . ?
N2 C1 H1 125.1 . . ?
C2 C1 H1 125.1 . . ?
C7 C2 C1 105.4(3) . . ?
C7 C2 C3 119.9(3) . . ?
C1 C2 C3 134.7(4) . . ?
C4 C3 C2 117.3(4) . . ?
C4 C3 H3 121.4 . . ?
C2 C3 H3 121.4 . . ?
C3 C4 C5 121.9(4) . . ?
C3 C4 H4 119.0 . . ?
C5 C4 H4 119.0 . . ?
C6 C5 C4 122.5(4) . . ?
C6 C5 H5 118.8 . . ?
C4 C5 H5 118.8 . . ?
C5 C6 C7 116.0(4) . . ?
C5 C6 H6 122.0 . . ?
C7 C6 H6 122.0 . . ?
N1 C7 C6 130.6(3) . . ?
N1 C7 C2 107.1(3) . . ?
C6 C7 C2 122.3(3) . . ?
N4 C8 C9 110.0(3) . . ?
N4 C8 H8 125.0 . . ?
C9 C8 H8 125.0 . . ?
C14 C9 C10 119.1(3) . . ?
C14 C9 C8 105.6(3) . . ?
C10 C9 C8 135.3(4) . . ?
C11 C10 C9 118.2(4) . . ?
C11 C10 H10 120.9 . . ?
C9 C10 H10 120.9 . . ?
C10 C11 C12 121.7(4) . . ?
C10 C11 H11 119.2 . . ?
C12 C11 H11 119.2 . . ?
C13 C12 C11 122.4(4) . . ?
C13 C12 H12 118.8 . . ?
C11 C12 H12 118.8 . . ?
C12 C13 C14 115.7(3) . . ?
C12 C13 H13 122.2 . . ?
C14 C13 H13 122.2 . . ?
N3 C14 C9 106.5(3) . . ?
N3 C14 C13 130.5(3) . . ?
C9 C14 C13 123.0(3) . . ?
N3 C15 N1 110.1(3) . . ?
N3 C15 H15A 109.6 . . ?
N1 C15 H15A 109.6 . . ?
N3 C15 H15B 109.6 . . ?
N1 C15 H15B 109.6 . . ?
H15A C15 H15B 108.2 . . ?
O1 C16 O2 126.5(4) . . ?
O1 C16 C17 115.1(4) . . ?
O2 C16 C17 118.4(4) . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
O4 C18 O3 124.8(4) . . ?
O4 C18 C19 121.5(4) . . ?
O3 C18 C19 113.7(3) . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O3 Pd1 O1 C16 95.4(3) . . . . ?
N4 Pd1 O1 C16 -83.4(3) . . . . ?
N2 Pd1 O3 C18 -65.6(3) . . . . ?
O1 Pd1 O3 C18 113.1(3) . . . . ?
C7 N1 N2 C1 -3.1(4) . . . . ?
C15 N1 N2 C1 -172.2(3) . . . . ?
C7 N1 N2 Pd1 164.5(2) . . . . ?
C15 N1 N2 Pd1 -4.6(4) . . . . ?
O3 Pd1 N2 C1 -54.6(3) . . . . ?
N4 Pd1 N2 C1 124.2(3) . . . . ?
O3 Pd1 N2 N1 141.2(2) . . . . ?
N4 Pd1 N2 N1 -40.0(3) . . . . ?
C14 N3 N4 C8 -0.7(4) . . . . ?
C15 N3 N4 C8 176.5(3) . . . . ?
C14 N3 N4 Pd1 -177.9(2) . . . . ?
C15 N3 N4 Pd1 -0.6(4) . . . . ?
N2 Pd1 N4 C8 -133.6(4) . . . . ?
O1 Pd1 N4 C8 47.8(4) . . . . ?
N2 Pd1 N4 N3 42.6(3) . . . . ?
O1 Pd1 N4 N3 -135.9(3) . . . . ?
N1 N2 C1 C2 1.8(4) . . . . ?
Pd1 N2 C1 C2 -163.7(3) . . . . ?
N2 C1 C2 C7 0.1(4) . . . . ?
N2 C1 C2 C3 -179.4(4) . . . . ?
C7 C2 C3 C4 2.3(6) . . . . ?
C1 C2 C3 C4 -178.3(4) . . . . ?
C2 C3 C4 C5 -1.2(7) . . . . ?
C3 C4 C5 C6 -0.4(7) . . . . ?
C4 C5 C6 C7 0.8(6) . . . . ?
N2 N1 C7 C6 -177.3(4) . . . . ?
C15 N1 C7 C6 -10.4(6) . . . . ?
N2 N1 C7 C2 3.1(4) . . . . ?
C15 N1 C7 C2 169.9(3) . . . . ?
C5 C6 C7 N1 -179.2(4) . . . . ?
C5 C6 C7 C2 0.4(5) . . . . ?
C1 C2 C7 N1 -1.9(4) . . . . ?
C3 C2 C7 N1 177.7(3) . . . . ?
C1 C2 C7 C6 178.4(3) . . . . ?
C3 C2 C7 C6 -2.0(6) . . . . ?
N3 N4 C8 C9 1.0(4) . . . . ?
Pd1 N4 C8 C9 177.5(3) . . . . ?
N4 C8 C9 C14 -1.0(4) . . . . ?
N4 C8 C9 C10 178.0(4) . . . . ?
C14 C9 C10 C11 -0.2(5) . . . . ?
C8 C9 C10 C11 -179.1(4) . . . . ?
C9 C10 C11 C12 0.9(6) . . . . ?
C10 C11 C12 C13 -1.4(6) . . . . ?
C11 C12 C13 C14 1.0(5) . . . . ?
N4 N3 C14 C9 0.1(4) . . . . ?
C15 N3 C14 C9 -176.7(3) . . . . ?
N4 N3 C14 C13 -178.3(4) . . . . ?
C15 N3 C14 C13 4.9(6) . . . . ?
C10 C9 C14 N3 -178.7(3) . . . . ?
C8 C9 C14 N3 0.5(4) . . . . ?
C10 C9 C14 C13 -0.1(5) . . . . ?
C8 C9 C14 C13 179.1(3) . . . . ?
C12 C13 C14 N3 177.9(4) . . . . ?
C12 C13 C14 C9 -0.3(5) . . . . ?
C14 N3 C15 N1 115.8(4) . . . . ?
N4 N3 C15 N1 -60.8(4) . . . . ?
C7 N1 C15 N3 -102.4(4) . . . . ?
N2 N1 C15 N3 63.7(4) . . . . ?
Pd1 O1 C16 O2 -1.7(6) . . . . ?
Pd1 O1 C16 C17 178.5(3) . . . . ?
Pd1 O3 C18 O4 -6.4(5) . . . . ?
Pd1 O3 C18 C19 173.6(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        25.25
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         1.080
_refine_diff_density_min         -0.466
_refine_diff_density_rms         0.089


loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.011 0.011 0.000 220 77 ' '
_platon_squeeze_details          
;
;
####################################################################### 
# 
# 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_7H2O
_database_code_depnum_ccdc_archive 'CCDC 1435382'
_audit_update_record             
;
2015-11-05 deposited with the CCDC.
2016-01-08 downloaded from the CCDC.
;


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H18 N4 O4 Pd, H2 O'
_chemical_formula_sum            'C19 H20 N4 O5 Pd'
_chemical_formula_weight         490.79

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           Triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.8396(4)
_cell_length_b                   10.9300(6)
_cell_length_c                   11.5282(6)
_cell_angle_alpha                111.8050(10)
_cell_angle_beta                 97.5450(10)
_cell_angle_gamma                96.2910(10)
_cell_volume                     1009.89(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    291(2)
_cell_measurement_reflns_used    9934
_cell_measurement_theta_min      2.84
_cell_measurement_theta_max      30.37

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.614
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             496
_exptl_absorpt_coefficient_mu    0.957
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8609
_exptl_absorpt_correction_T_max  0.9094
_exptl_absorpt_process_details   
;
program SADABS, Bruker (2001).
;
_diffrn_ambient_temperature      291(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  
;
 Bruker-Nonius X8kappa APEX II CCD area detector
;
_diffrn_measurement_method       'phi and omega scans with narrow frames'
_diffrn_detector_area_resol_mean 8.26
_diffrn_standards_decay_%        0
_diffrn_reflns_number            16409
_diffrn_reflns_av_R_equivalents  0.0181
_diffrn_reflns_av_sigmaI/netI    0.0152
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         1.94
_diffrn_reflns_theta_max         25.25
_reflns_number_total             3614
_reflns_number_gt                3307
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 Software Suite (Bruker, 2007)'
_computing_cell_refinement       'APEX2 Software Suite (Bruker, 2007)'
_computing_data_reduction        'APEX2 Software Suite (Bruker, 2007)'
_computing_structure_solution    'SIR2002 (Burla et al., 2003)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL and publCIF (Westrip, 2010)'

_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)+(0.0334P)²+0.5493P] 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         3614
_refine_ls_number_parameters     270
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0264
_refine_ls_R_factor_gt           0.0227
_refine_ls_wR_factor_ref         0.0609
_refine_ls_wR_factor_gt          0.0590
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_restrained_S_all      1.015
_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 0.028128(18) 0.135913(15) 0.683059(16) 0.03580(7) Uani 1 1 d . . .
O1 O 0.1379(2) 0.00191(16) 0.72424(17) 0.0495(4) Uani 1 1 d . . .
O2 O 0.1334(2) 0.1021(2) 0.92977(19) 0.0653(5) Uani 1 1 d . . .
O3 O -0.16722(19) -0.00203(15) 0.60607(17) 0.0465(4) Uani 1 1 d . . .
O4 O -0.3011(2) 0.1169(2) 0.7474(2) 0.0701(6) Uani 1 1 d . . .
N1 N -0.0273(2) 0.40307(17) 0.70351(17) 0.0350(4) Uani 1 1 d . . .
N2 N -0.0718(2) 0.26959(17) 0.63095(17) 0.0357(4) Uani 1 1 d . . .
N3 N 0.22211(19) 0.40223(17) 0.80723(17) 0.0346(4) Uani 1 1 d . . .
N4 N 0.2274(2) 0.26871(18) 0.75581(17) 0.0365(4) Uani 1 1 d . . .
C1 C -0.1661(3) 0.2569(2) 0.5278(2) 0.0427(5) Uani 1 1 d . . .
H1 H -0.2120 0.1758 0.4621 0.051 Uiso 1 1 calc R . .
C2 C -0.1880(3) 0.3843(2) 0.5308(2) 0.0407(5) Uani 1 1 d . . .
C3 C -0.2756(3) 0.4329(3) 0.4511(3) 0.0566(7) Uani 1 1 d . . .
H3 H -0.3406 0.3747 0.3760 0.068 Uiso 1 1 calc R . .
C4 C -0.2620(4) 0.5675(3) 0.4875(3) 0.0629(8) Uani 1 1 d . . .
H4 H -0.3196 0.6009 0.4363 0.075 Uiso 1 1 calc R . .
C5 C -0.1638(3) 0.6581(3) 0.6001(3) 0.0561(7) Uani 1 1 d . . .
H5 H -0.1563 0.7495 0.6200 0.067 Uiso 1 1 calc R . .
C6 C -0.0792(3) 0.6150(2) 0.6810(3) 0.0455(5) Uani 1 1 d . . .
H6 H -0.0154 0.6744 0.7562 0.055 Uiso 1 1 calc R . .
C7 C -0.0941(2) 0.4762(2) 0.6442(2) 0.0350(5) Uani 1 1 d . . .
C8 C 0.3744(3) 0.2560(2) 0.7538(2) 0.0407(5) Uani 1 1 d . . .
H8 H 0.4102 0.1751 0.7237 0.049 Uiso 1 1 calc R . .
C9 C 0.4687(2) 0.3836(2) 0.8040(2) 0.0386(5) Uani 1 1 d . . .
C10 C 0.6290(3) 0.4306(3) 0.8257(2) 0.0503(6) Uani 1 1 d . . .
H10 H 0.6991 0.3718 0.8052 0.060 Uiso 1 1 calc R . .
C11 C 0.6771(3) 0.5658(3) 0.8778(2) 0.0551(7) Uani 1 1 d . . .
H11 H 0.7824 0.5992 0.8934 0.066 Uiso 1 1 calc R . .
C12 C 0.5733(3) 0.6561(3) 0.9087(2) 0.0518(6) Uani 1 1 d . . .
H12 H 0.6116 0.7474 0.9426 0.062 Uiso 1 1 calc R . .
C13 C 0.4167(3) 0.6136(2) 0.8905(2) 0.0426(5) Uani 1 1 d . . .
H13 H 0.3479 0.6734 0.9121 0.051 Uiso 1 1 calc R . .
C14 C 0.3671(2) 0.4754(2) 0.83757(19) 0.0335(4) Uani 1 1 d . . .
C15 C 0.0743(2) 0.4437(2) 0.8248(2) 0.0347(5) Uani 1 1 d . . .
H15A H 0.0275 0.4038 0.8769 0.042 Uiso 1 1 calc R . .
H15B H 0.0894 0.5401 0.8687 0.042 Uiso 1 1 calc R . .
C16 C 0.1726(3) 0.0181(2) 0.8401(3) 0.0474(6) Uani 1 1 d . . .
C17 C 0.2769(4) -0.0743(3) 0.8635(4) 0.0763(9) Uani 1 1 d . . .
H17A H 0.3832 -0.0333 0.8782 0.115 Uiso 1 1 calc R . .
H17B H 0.2570 -0.1574 0.7905 0.115 Uiso 1 1 calc R . .
H17C H 0.2568 -0.0908 0.9367 0.115 Uiso 1 1 calc R . .
C18 C -0.2873(3) 0.0176(2) 0.6577(3) 0.0491(6) Uani 1 1 d . . .
C19 C -0.4227(3) -0.0971(3) 0.5966(3) 0.0742(9) Uani 1 1 d . . .
H19A H -0.4224 -0.1536 0.6435 0.111 Uiso 1 1 calc R . .
H19B H -0.4137 -0.1482 0.5105 0.111 Uiso 1 1 calc R . .
H19C H -0.5178 -0.0623 0.5970 0.111 Uiso 1 1 calc R . .
O5 O 0.9083(3) 0.2613(2) 0.97511(19) 0.0614(5) Uani 1 1 d D . .
H1O H 0.836(3) 0.232(4) 0.912(3) 0.092 Uiso 1 1 d D . .
H2O H 0.974(3) 0.213(3) 0.958(3) 0.092 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 O1 2.0049(16) . ?
Pd1 N4 2.0152(18) . ?
Pd1 N2 2.0177(18) . ?
Pd1 O3 2.0189(16) . ?
O1 C16 1.270(3) . ?
O2 C16 1.221(3) . ?
O3 C18 1.284(3) . ?
O4 C18 1.221(3) . ?
N1 C7 1.363(3) . ?
N1 N2 1.365(2) . ?
N1 C15 1.443(3) . ?
N2 C1 1.312(3) . ?
N3 C14 1.362(3) . ?
N3 N4 1.365(2) . ?
N3 C15 1.443(3) . ?
N4 C8 1.324(3) . ?
C1 C2 1.416(3) . ?
C1 H1 0.9300 . ?
C2 C7 1.402(3) . ?
C2 C3 1.411(3) . ?
C3 C4 1.357(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.407(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.369(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.400(3) . ?
C6 H6 0.9300 . ?
C8 C9 1.411(3) . ?
C8 H8 0.9300 . ?
C9 C14 1.401(3) . ?
C9 C10 1.409(3) . ?
C10 C11 1.365(4) . ?
C10 H10 0.9300 . ?
C11 C12 1.402(4) . ?
C11 H11 0.9300 . ?
C12 C13 1.373(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.395(3) . ?
C13 H13 0.9300 . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 C17 1.511(4) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 C19 1.515(4) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
O5 H1O 0.838(17) . ?
O5 H2O 0.821(17) . ?

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
O1 Pd1 N4 88.66(7) . . ?
O1 Pd1 N2 175.40(7) . . ?
N4 Pd1 N2 89.65(7) . . ?
O1 Pd1 O3 90.03(7) . . ?
N4 Pd1 O3 177.88(6) . . ?
N2 Pd1 O3 91.52(7) . . ?
C16 O1 Pd1 118.34(15) . . ?
C18 O3 Pd1 119.13(15) . . ?
C7 N1 N2 110.24(17) . . ?
C7 N1 C15 131.20(18) . . ?
N2 N1 C15 118.55(17) . . ?
C1 N2 N1 107.74(18) . . ?
C1 N2 Pd1 132.23(16) . . ?
N1 N2 Pd1 119.57(13) . . ?
C14 N3 N4 110.46(16) . . ?
C14 N3 C15 130.77(18) . . ?
N4 N3 C15 118.73(17) . . ?
C8 N4 N3 107.51(18) . . ?
C8 N4 Pd1 132.62(16) . . ?
N3 N4 Pd1 119.45(13) . . ?
N2 C1 C2 110.2(2) . . ?
N2 C1 H1 124.9 . . ?
C2 C1 H1 124.9 . . ?
C7 C2 C3 118.9(2) . . ?
C7 C2 C1 105.1(2) . . ?
C3 C2 C1 136.0(2) . . ?
C4 C3 C2 117.9(3) . . ?
C4 C3 H3 121.1 . . ?
C2 C3 H3 121.1 . . ?
C3 C4 C5 122.4(3) . . ?
C3 C4 H4 118.8 . . ?
C5 C4 H4 118.8 . . ?
C6 C5 C4 121.5(3) . . ?
C6 C5 H5 119.3 . . ?
C4 C5 H5 119.3 . . ?
C5 C6 C7 116.3(2) . . ?
C5 C6 H6 121.9 . . ?
C7 C6 H6 121.9 . . ?
N1 C7 C6 130.3(2) . . ?
N1 C7 C2 106.64(19) . . ?
C6 C7 C2 123.1(2) . . ?
N4 C8 C9 109.9(2) . . ?
N4 C8 H8 125.0 . . ?
C9 C8 H8 125.0 . . ?
C14 C9 C10 119.6(2) . . ?
C14 C9 C8 105.51(19) . . ?
C10 C9 C8 134.9(2) . . ?
C11 C10 C9 117.3(2) . . ?
C11 C10 H10 121.4 . . ?
C9 C10 H10 121.4 . . ?
C10 C11 C12 122.3(2) . . ?
C10 C11 H11 118.9 . . ?
C12 C11 H11 118.9 . . ?
C13 C12 C11 121.9(2) . . ?
C13 C12 H12 119.0 . . ?
C11 C12 H12 119.0 . . ?
C12 C13 C14 116.0(2) . . ?
C12 C13 H13 122.0 . . ?
C14 C13 H13 122.0 . . ?
N3 C14 C13 130.4(2) . . ?
N3 C14 C9 106.60(19) . . ?
C13 C14 C9 123.0(2) . . ?
N1 C15 N3 110.29(17) . . ?
N1 C15 H15A 109.6 . . ?
N3 C15 H15A 109.6 . . ?
N1 C15 H15B 109.6 . . ?
N3 C15 H15B 109.6 . . ?
H15A C15 H15B 108.1 . . ?
O2 C16 O1 125.9(2) . . ?
O2 C16 C17 119.7(3) . . ?
O1 C16 C17 114.3(3) . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
O4 C18 O3 126.8(2) . . ?
O4 C18 C19 119.2(3) . . ?
O3 C18 C19 114.1(2) . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
H1O O5 H2O 107(2) . . ?

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
N4 Pd1 O1 C16 72.24(18) . . . . ?
O3 Pd1 O1 C16 -109.44(18) . . . . ?
O1 Pd1 O3 C18 115.76(19) . . . . ?
N2 Pd1 O3 C18 -68.57(19) . . . . ?
C7 N1 N2 C1 -0.5(2) . . . . ?
C15 N1 N2 C1 178.33(18) . . . . ?
C7 N1 N2 Pd1 172.62(13) . . . . ?
C15 N1 N2 Pd1 -8.6(2) . . . . ?
N4 Pd1 N2 C1 138.6(2) . . . . ?
O3 Pd1 N2 C1 -39.6(2) . . . . ?
N4 Pd1 N2 N1 -32.53(16) . . . . ?
O3 Pd1 N2 N1 149.24(15) . . . . ?
C14 N3 N4 C8 0.4(2) . . . . ?
C15 N3 N4 C8 -177.68(19) . . . . ?
C14 N3 N4 Pd1 -173.02(13) . . . . ?
C15 N3 N4 Pd1 8.9(2) . . . . ?
O1 Pd1 N4 C8 36.6(2) . . . . ?
N2 Pd1 N4 C8 -139.1(2) . . . . ?
O1 Pd1 N4 N3 -151.98(16) . . . . ?
N2 Pd1 N4 N3 32.30(16) . . . . ?
N1 N2 C1 C2 -0.8(3) . . . . ?
Pd1 N2 C1 C2 -172.68(15) . . . . ?
N2 C1 C2 C7 1.7(3) . . . . ?
N2 C1 C2 C3 -178.5(3) . . . . ?
C7 C2 C3 C4 1.3(4) . . . . ?
C1 C2 C3 C4 -178.5(3) . . . . ?
C2 C3 C4 C5 0.5(4) . . . . ?
C3 C4 C5 C6 -1.7(4) . . . . ?
C4 C5 C6 C7 1.0(4) . . . . ?
N2 N1 C7 C6 -178.3(2) . . . . ?
C15 N1 C7 C6 3.1(4) . . . . ?
N2 N1 C7 C2 1.5(2) . . . . ?
C15 N1 C7 C2 -177.1(2) . . . . ?
C5 C6 C7 N1 -179.5(2) . . . . ?
C5 C6 C7 C2 0.8(3) . . . . ?
C3 C2 C7 N1 178.2(2) . . . . ?
C1 C2 C7 N1 -1.9(2) . . . . ?
C3 C2 C7 C6 -1.9(3) . . . . ?
C1 C2 C7 C6 177.9(2) . . . . ?
N3 N4 C8 C9 -0.4(3) . . . . ?
Pd1 N4 C8 C9 171.79(16) . . . . ?
N4 C8 C9 C14 0.3(3) . . . . ?
N4 C8 C9 C10 179.5(2) . . . . ?
C14 C9 C10 C11 -0.8(3) . . . . ?
C8 C9 C10 C11 -179.9(3) . . . . ?
C9 C10 C11 C12 -0.3(4) . . . . ?
C10 C11 C12 C13 1.2(4) . . . . ?
C11 C12 C13 C14 -1.0(4) . . . . ?
N4 N3 C14 C13 179.3(2) . . . . ?
C15 N3 C14 C13 -3.0(4) . . . . ?
N4 N3 C14 C9 -0.2(2) . . . . ?
C15 N3 C14 C9 177.5(2) . . . . ?
C12 C13 C14 N3 -179.6(2) . . . . ?
C12 C13 C14 C9 -0.2(3) . . . . ?
C10 C9 C14 N3 -179.4(2) . . . . ?
C8 C9 C14 N3 0.0(2) . . . . ?
C10 C9 C14 C13 1.0(3) . . . . ?
C8 C9 C14 C13 -179.6(2) . . . . ?
C7 N1 C15 N3 -117.6(2) . . . . ?
N2 N1 C15 N3 63.9(2) . . . . ?
C14 N3 C15 N1 118.2(2) . . . . ?
N4 N3 C15 N1 -64.2(2) . . . . ?
Pd1 O1 C16 O2 6.8(4) . . . . ?
Pd1 O1 C16 C17 -170.67(19) . . . . ?
Pd1 O3 C18 O4 4.5(4) . . . . ?
Pd1 O3 C18 C19 -176.1(2) . . . . ?

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
O5 H2O O2 0.821(17) 1.940(17) 2.760(3) 176(3) 1_655
O5 H1O O4 0.838(17) 1.98(2) 2.796(3) 163(3) 1_655

_diffrn_measured_fraction_theta_max 0.988
_diffrn_reflns_theta_full        25.25
_diffrn_measured_fraction_theta_full 0.988
_refine_diff_density_max         0.485
_refine_diff_density_min         -0.412
_refine_diff_density_rms         0.055


###END





