# 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 2017

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_mo_HUNUMAN_29816_0m
_database_code_depnum_ccdc_archive 'CCDC 1502139'
_audit_update_record             
;
2016-09-01 deposited with the CCDC.
2017-03-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H18 I N3 O Pd'
_chemical_formula_sum            'C15 H18 I N3 O Pd'
_chemical_formula_weight         489.62

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   10.5522(12)
_cell_length_b                   11.3163(18)
_cell_length_c                   13.8002(13)
_cell_angle_alpha                90
_cell_angle_beta                 104.277(4)
_cell_angle_gamma                90
_cell_volume                     1597.0(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9697
_cell_measurement_theta_min      2.84
_cell_measurement_theta_max      33.71

_exptl_crystal_description       PLATE
_exptl_crystal_colour            BROWN
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.036
_exptl_crystal_F_000             944
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.190
_exptl_crystal_size_min          0.110
_exptl_absorpt_coefficient_mu    3.097
_shelx_estimated_absorpt_T_min   0.549
_shelx_estimated_absorpt_T_max   0.727
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.549
_exptl_absorpt_correction_T_max  0.727
_exptl_absorpt_process_details   'SADABS-2014/5 (Sheldrick, 2014)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'I\mS HB Micro-focus sealed tube'
_diffrn_radiation_monochromator  'multilayer mirrors'
_diffrn_source_type              'Incoatech I\mS HB'
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE Kappa Duo PHOTON II CPAD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector                 'PHoton II CPAD Area Detector'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            63587
_diffrn_reflns_av_unetI/netI     0.0257
_diffrn_reflns_av_R_equivalents  0.0511
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.685
_diffrn_reflns_theta_max         33.498
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             6134
_reflns_number_gt                5555
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+0.7894P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.00170(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         6134
_refine_ls_number_parameters     193
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0253
_refine_ls_R_factor_gt           0.0195
_refine_ls_wR_factor_ref         0.0392
_refine_ls_wR_factor_gt          0.0379
_refine_ls_goodness_of_fit_ref   1.190
_refine_ls_restrained_S_all      1.190
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Pd1 Pd 0.79627(2) 0.29533(2) 0.54602(2) 0.01213(3) Uani 1 1 d . . . . .
I1 I 1.05040(2) 0.30831(2) 0.57003(2) 0.01918(3) Uani 1 1 d . . . . .
O1 O 0.42908(10) 0.15940(10) 0.48781(10) 0.0277(2) Uani 1 1 d . . . . .
N1 N 0.60873(11) 0.28047(10) 0.53986(9) 0.0156(2) Uani 1 1 d . . . . .
N2 N 0.77126(11) 0.45253(10) 0.60971(8) 0.0143(2) Uani 1 1 d . . . . .
N3 N 0.77270(11) 0.12902(10) 0.47997(8) 0.0162(2) Uani 1 1 d . . . . .
C1 C 0.55662(12) 0.37023(12) 0.58760(10) 0.0154(2) Uani 1 1 d . . . . .
C2 C 0.43092(13) 0.37816(13) 0.60146(11) 0.0201(3) Uani 1 1 d . . . . .
H2 H 0.3689 0.3176 0.5769 0.024 Uiso 1 1 calc R U . . .
C3 C 0.39568(14) 0.47634(14) 0.65204(12) 0.0240(3) Uani 1 1 d . . . . .
H3 H 0.3098 0.4802 0.6618 0.029 Uiso 1 1 calc R U . . .
C4 C 0.48135(15) 0.56631(14) 0.68747(11) 0.0234(3) Uani 1 1 d . . . . .
H4 H 0.4549 0.6310 0.7217 0.028 Uiso 1 1 calc R U . . .
C5 C 0.60949(14) 0.56260(13) 0.67292(10) 0.0186(2) Uani 1 1 d . . . . .
C6 C 0.70300(16) 0.65340(13) 0.70319(11) 0.0235(3) Uani 1 1 d . . . . .
H6 H 0.6816 0.7218 0.7359 0.028 Uiso 1 1 calc R U . . .
C7 C 0.82447(16) 0.64242(13) 0.68523(11) 0.0237(3) Uani 1 1 d . . . . .
H7 H 0.8872 0.7037 0.7043 0.028 Uiso 1 1 calc R U . . .
C8 C 0.85575(14) 0.54002(13) 0.63853(10) 0.0187(3) Uani 1 1 d . . . . .
H8 H 0.9406 0.5332 0.6272 0.022 Uiso 1 1 calc R U . . .
C9 C 0.64639(13) 0.46315(12) 0.62403(9) 0.0146(2) Uani 1 1 d . . . . .
C10 C 0.54436(13) 0.18489(13) 0.49423(11) 0.0188(3) Uani 1 1 d . . . . .
C11 C 0.62749(14) 0.10931(13) 0.44267(11) 0.0204(3) Uani 1 1 d . . . . .
H11A H 0.6084 0.0250 0.4521 0.024 Uiso 1 1 calc R U . . .
H11B H 0.6017 0.1259 0.3700 0.024 Uiso 1 1 calc R U . . .
C12 C 0.83006(15) 0.03472(13) 0.55419(11) 0.0214(3) Uani 1 1 d . . . . .
H12B H 0.9258 0.0469 0.5760 0.026 Uiso 1 1 calc R U . . .
H12A H 0.8149 -0.0430 0.5203 0.026 Uiso 1 1 calc R U . . .
C13 C 0.77561(16) 0.03081(14) 0.64603(11) 0.0253(3) Uani 1 1 d . . . . .
H13A H 0.7901 0.1072 0.6804 0.038 Uiso 1 1 calc R U . . .
H13C H 0.8199 -0.0315 0.6912 0.038 Uiso 1 1 calc R U . . .
H13B H 0.6816 0.0142 0.6258 0.038 Uiso 1 1 calc R U . . .
C14 C 0.83629(14) 0.11676(13) 0.39438(10) 0.0209(3) Uani 1 1 d . . . . .
H14B H 0.8059 0.0424 0.3583 0.025 Uiso 1 1 calc R U . . .
H14A H 0.9321 0.1105 0.4215 0.025 Uiso 1 1 calc R U . . .
C15 C 0.80819(16) 0.21816(15) 0.32061(11) 0.0247(3) Uani 1 1 d . . . . .
H15A H 0.8579 0.2072 0.2699 0.037 Uiso 1 1 calc R U . . .
H15B H 0.8340 0.2928 0.3560 0.037 Uiso 1 1 calc R U . . .
H15C H 0.7145 0.2201 0.2881 0.037 Uiso 1 1 calc R U . . .


_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 1.9669(11) . ?
Pd1 N2 2.0300(11) . ?
Pd1 N3 2.0792(12) . ?
Pd1 I1 2.6238(3) . ?
O1 C10 1.2319(17) . ?
N1 C10 1.3479(18) . ?
N1 C1 1.3953(17) . ?
N2 C8 1.3261(17) . ?
N2 C9 1.3849(16) . ?
N3 C12 1.4994(18) . ?
N3 C14 1.5019(17) . ?
N3 C11 1.5079(18) . ?
C1 C2 1.3890(18) . ?
C1 C9 1.4216(19) . ?
C2 C3 1.410(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.369(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.416(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.414(2) . ?
C5 C9 1.4153(18) . ?
C6 C7 1.370(2) . ?
C6 H6 0.9500 . ?
C7 C8 1.404(2) . ?
C7 H7 0.9500 . ?
C8 H8 0.9500 . ?
C10 C11 1.522(2) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.516(2) . ?
C12 H12B 0.9900 . ?
C12 H12A 0.9900 . ?
C13 H13A 0.9800 . ?
C13 H13C 0.9800 . ?
C13 H13B 0.9800 . ?
C14 C15 1.514(2) . ?
C14 H14B 0.9900 . ?
C14 H14A 0.9900 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 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
N1 Pd1 N2 81.77(5) . . ?
N1 Pd1 N3 83.88(5) . . ?
N2 Pd1 N3 165.64(4) . . ?
N1 Pd1 I1 175.08(3) . . ?
N2 Pd1 I1 97.71(3) . . ?
N3 Pd1 I1 96.55(3) . . ?
C10 N1 C1 126.36(12) . . ?
C10 N1 Pd1 118.33(9) . . ?
C1 N1 Pd1 115.27(9) . . ?
C8 N2 C9 119.04(12) . . ?
C8 N2 Pd1 129.39(9) . . ?
C9 N2 Pd1 111.57(8) . . ?
C12 N3 C14 106.75(11) . . ?
C12 N3 C11 109.45(11) . . ?
C14 N3 C11 109.35(11) . . ?
C12 N3 Pd1 111.11(9) . . ?
C14 N3 Pd1 113.58(9) . . ?
C11 N3 Pd1 106.57(8) . . ?
C2 C1 N1 127.81(13) . . ?
C2 C1 C9 118.64(12) . . ?
N1 C1 C9 113.55(11) . . ?
C1 C2 C3 119.77(14) . . ?
C1 C2 H2 120.1 . . ?
C3 C2 H2 120.1 . . ?
C4 C3 C2 122.09(13) . . ?
C4 C3 H3 119.0 . . ?
C2 C3 H3 119.0 . . ?
C3 C4 C5 119.79(13) . . ?
C3 C4 H4 120.1 . . ?
C5 C4 H4 120.1 . . ?
C6 C5 C9 117.68(13) . . ?
C6 C5 C4 123.90(13) . . ?
C9 C5 C4 118.42(13) . . ?
C7 C6 C5 119.76(13) . . ?
C7 C6 H6 120.1 . . ?
C5 C6 H6 120.1 . . ?
C6 C7 C8 119.62(14) . . ?
C6 C7 H7 120.2 . . ?
C8 C7 H7 120.2 . . ?
N2 C8 C7 122.48(13) . . ?
N2 C8 H8 118.8 . . ?
C7 C8 H8 118.8 . . ?
N2 C9 C5 121.35(12) . . ?
N2 C9 C1 117.37(11) . . ?
C5 C9 C1 121.27(12) . . ?
O1 C10 N1 126.61(13) . . ?
O1 C10 C11 120.51(13) . . ?
N1 C10 C11 112.78(12) . . ?
N3 C11 C10 114.31(11) . . ?
N3 C11 H11A 108.7 . . ?
C10 C11 H11A 108.7 . . ?
N3 C11 H11B 108.7 . . ?
C10 C11 H11B 108.7 . . ?
H11A C11 H11B 107.6 . . ?
N3 C12 C13 114.81(12) . . ?
N3 C12 H12B 108.6 . . ?
C13 C12 H12B 108.6 . . ?
N3 C12 H12A 108.6 . . ?
C13 C12 H12A 108.6 . . ?
H12B C12 H12A 107.5 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13C C13 H13B 109.5 . . ?
N3 C14 C15 114.05(12) . . ?
N3 C14 H14B 108.7 . . ?
C15 C14 H14B 108.7 . . ?
N3 C14 H14A 108.7 . . ?
C15 C14 H14A 108.7 . . ?
H14B C14 H14A 107.6 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 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
C10 N1 C1 C2 2.6(2) . . . . ?
Pd1 N1 C1 C2 -174.92(12) . . . . ?
C10 N1 C1 C9 -176.63(13) . . . . ?
Pd1 N1 C1 C9 5.85(15) . . . . ?
N1 C1 C2 C3 179.95(14) . . . . ?
C9 C1 C2 C3 -0.9(2) . . . . ?
C1 C2 C3 C4 0.9(2) . . . . ?
C2 C3 C4 C5 0.5(2) . . . . ?
C3 C4 C5 C6 177.37(15) . . . . ?
C3 C4 C5 C9 -1.7(2) . . . . ?
C9 C5 C6 C7 -0.4(2) . . . . ?
C4 C5 C6 C7 -179.50(15) . . . . ?
C5 C6 C7 C8 -1.2(2) . . . . ?
C9 N2 C8 C7 1.4(2) . . . . ?
Pd1 N2 C8 C7 -177.58(11) . . . . ?
C6 C7 C8 N2 0.7(2) . . . . ?
C8 N2 C9 C5 -3.06(19) . . . . ?
Pd1 N2 C9 C5 176.14(10) . . . . ?
C8 N2 C9 C1 176.89(12) . . . . ?
Pd1 N2 C9 C1 -3.92(14) . . . . ?
C6 C5 C9 N2 2.5(2) . . . . ?
C4 C5 C9 N2 -178.31(13) . . . . ?
C6 C5 C9 C1 -177.43(13) . . . . ?
C4 C5 C9 C1 1.7(2) . . . . ?
C2 C1 C9 N2 179.61(12) . . . . ?
N1 C1 C9 N2 -1.09(17) . . . . ?
C2 C1 C9 C5 -0.4(2) . . . . ?
N1 C1 C9 C5 178.86(12) . . . . ?
C1 N1 C10 O1 -1.0(2) . . . . ?
Pd1 N1 C10 O1 176.47(13) . . . . ?
C1 N1 C10 C11 175.52(12) . . . . ?
Pd1 N1 C10 C11 -7.02(16) . . . . ?
C12 N3 C11 C10 98.41(14) . . . . ?
C14 N3 C11 C10 -144.98(12) . . . . ?
Pd1 N3 C11 C10 -21.83(14) . . . . ?
O1 C10 C11 N3 -163.41(14) . . . . ?
N1 C10 C11 N3 19.85(18) . . . . ?
C14 N3 C12 C13 -178.75(12) . . . . ?
C11 N3 C12 C13 -60.50(15) . . . . ?
Pd1 N3 C12 C13 56.92(14) . . . . ?
C12 N3 C14 C15 -169.71(13) . . . . ?
C11 N3 C14 C15 71.98(15) . . . . ?
Pd1 N3 C14 C15 -46.90(15) . . . . ?



_refine_diff_density_max         0.703
_refine_diff_density_min         -0.634
_refine_diff_density_rms         0.122


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Chloroform-D-dichloromethane'
####################################################################### 
# 
# 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_ABC
_database_code_depnum_ccdc_archive 'CCDC 1487195'
_audit_update_record             
;
2016-06-22 deposited with the CCDC.
2017-03-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H23 N3 O4 Pd'
_chemical_formula_weight         439.78

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   10.8321(4)
_cell_length_b                   23.7645(8)
_cell_length_c                   6.9558(2)
_cell_angle_alpha                90
_cell_angle_beta                 103.107(2)
_cell_angle_gamma                90
_cell_volume                     1743.91(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    4806
_cell_measurement_theta_min      2.58
_cell_measurement_theta_max      30.56

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.675
_exptl_crystal_F_000             896
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.460
_exptl_crystal_size_mid          0.310
_exptl_crystal_size_min          0.210
_exptl_absorpt_coefficient_mu    1.091
_shelx_estimated_absorpt_T_min   0.634
_shelx_estimated_absorpt_T_max   0.803
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6342
_exptl_absorpt_correction_T_max  0.8033
_exptl_absorpt_process_details   'Bruker SADABS'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13765
_diffrn_reflns_av_unetI/netI     0.0390
_diffrn_reflns_av_R_equivalents  0.0411
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         1.714
_diffrn_reflns_theta_max         24.996
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.965
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.965
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.965
_reflns_number_total             3049
_reflns_number_gt                2597
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0002P)²+12.3600P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3049
_refine_ls_number_parameters     237
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0742
_refine_ls_R_factor_gt           0.0621
_refine_ls_wR_factor_ref         0.1099
_refine_ls_wR_factor_gt          0.1062
_refine_ls_goodness_of_fit_ref   1.300
_refine_ls_restrained_S_all      1.300
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Pd1 Pd 0.74702(5) 0.13286(2) 0.24319(8) 0.01716(15) Uani 1 1 d . . . . .
O1 O 0.9587(4) 0.27484(19) 0.3011(7) 0.0253(11) Uani 1 1 d . . . . .
O2 O 0.6921(4) 0.04991(18) 0.2173(7) 0.0224(11) Uani 1 1 d . . . . .
O3 O 0.7082(5) 0.0411(2) 0.5405(8) 0.0355(13) Uani 1 1 d . . . . .
N1 N 0.7903(5) 0.2120(2) 0.2534(8) 0.0180(12) Uani 1 1 d . . . . .
N2 N 0.5687(5) 0.1627(2) 0.1927(8) 0.0174(12) Uani 1 1 d . . . . .
N3 N 0.9416(5) 0.1214(2) 0.3098(7) 0.0167(12) Uani 1 1 d . . . . .
C1 C 0.6860(6) 0.2489(3) 0.2287(9) 0.0174(14) Uani 1 1 d . . . . .
C2 C 0.6870(7) 0.3066(3) 0.2262(10) 0.0225(15) Uani 1 1 d . . . . .
H2 H 0.7652 0.3263 0.2468 0.027 Uiso 1 1 calc R U . . .
C3 C 0.5723(7) 0.3367(3) 0.1934(10) 0.0266(16) Uani 1 1 d . . . . .
H3 H 0.5749 0.3766 0.1927 0.032 Uiso 1 1 calc R U . . .
C4 C 0.4583(7) 0.3107(3) 0.1627(11) 0.0289(17) Uani 1 1 d . . . . .
H4 H 0.3826 0.3322 0.1412 0.035 Uiso 1 1 calc R U . . .
C5 C 0.4528(6) 0.2510(3) 0.1628(10) 0.0234(16) Uani 1 1 d . . . . .
C6 C 0.3399(7) 0.2196(3) 0.1268(11) 0.0293(17) Uani 1 1 d . . . . .
H6 H 0.2606 0.2386 0.1019 0.035 Uiso 1 1 calc R U . . .
C7 C 0.3428(6) 0.1621(3) 0.1271(10) 0.0278(17) Uani 1 1 d . . . . .
H7 H 0.2665 0.1409 0.1058 0.033 Uiso 1 1 calc R U . . .
C8 C 0.4609(6) 0.1349(3) 0.1595(10) 0.0242(15) Uani 1 1 d . . . . .
H8 H 0.4630 0.0950 0.1573 0.029 Uiso 1 1 calc R U . . .
C9 C 0.5665(6) 0.2206(3) 0.1940(9) 0.0198(15) Uani 1 1 d . . . . .
C10 C 0.9122(6) 0.2273(3) 0.2800(10) 0.0212(16) Uani 1 1 d . . . . .
C11 C 0.9977(6) 0.1772(3) 0.2726(10) 0.0211(15) Uani 1 1 d . . . . .
H11A H 1.0184 0.1761 0.1412 0.025 Uiso 1 1 calc R U . . .
H11B H 1.0780 0.1826 0.3722 0.025 Uiso 1 1 calc R U . . .
C12 C 0.9830(7) 0.0750(3) 0.1955(10) 0.0242(16) Uani 1 1 d . . . . .
H12A H 0.9563 0.0386 0.2421 0.029 Uiso 1 1 calc R U . . .
H12B H 1.0767 0.0750 0.2207 0.029 Uiso 1 1 calc R U . . .
C13 C 0.9288(8) 0.0802(3) -0.0233(10) 0.0325(18) Uani 1 1 d . . . . .
H13A H 0.8362 0.0781 -0.0499 0.049 Uiso 1 1 calc R U . . .
H13B H 0.9611 0.0496 -0.0924 0.049 Uiso 1 1 calc R U . . .
H13C H 0.9541 0.1165 -0.0700 0.049 Uiso 1 1 calc R U . . .
C14 C 0.9772(6) 0.1093(3) 0.5278(9) 0.0225(15) Uani 1 1 d . . . . .
H14A H 0.9246 0.0777 0.5563 0.027 Uiso 1 1 calc R U . . .
H14B H 0.9565 0.1427 0.5994 0.027 Uiso 1 1 calc R U . . .
C15 C 1.1169(7) 0.0945(4) 0.6082(12) 0.042(2) Uani 1 1 d . . . . .
H15A H 1.1368 0.0595 0.5476 0.063 Uiso 1 1 calc R U . . .
H15B H 1.1332 0.0898 0.7517 0.063 Uiso 1 1 calc R U . . .
H15C H 1.1702 0.1249 0.5768 0.063 Uiso 1 1 calc R U . . .
C16 C 0.6729(6) 0.0239(3) 0.3706(11) 0.0250(16) Uani 1 1 d . . . . .
C17 C 0.5992(7) -0.0301(3) 0.3259(12) 0.0315(18) Uani 1 1 d . . . . .
H17A H 0.6136 -0.0534 0.4450 0.047 Uiso 1 1 calc R U . . .
H17B H 0.6274 -0.0504 0.2210 0.047 Uiso 1 1 calc R U . . .
H17C H 0.5086 -0.0215 0.2827 0.047 Uiso 1 1 calc R U . . .
O4 O 0.2848(6) 0.4751(3) 0.6140(11) 0.0399(15) Uani 1 1 d . . . . .
H4A H 0.263(9) 0.497(4) 0.692(14) 0.06(4) Uiso 1 1 d . . . . .
H4B H 0.289(8) 0.494(4) 0.512(14) 0.05(3) Uiso 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 1.936(5) . ?
Pd1 N2 2.012(5) . ?
Pd1 O2 2.055(4) . ?
Pd1 N3 2.070(5) . ?
O1 C10 1.232(8) . ?
O2 C16 1.289(8) . ?
O3 C16 1.227(9) . ?
N1 C10 1.342(8) . ?
N1 C1 1.409(8) . ?
N2 C8 1.315(8) . ?
N2 C9 1.378(8) . ?
N3 C12 1.487(8) . ?
N3 C14 1.504(8) . ?
N3 C11 1.506(8) . ?
C1 C2 1.373(9) . ?
C1 C9 1.429(9) . ?
C2 C3 1.406(10) . ?
C2 H2 0.9500 . ?
C3 C4 1.354(10) . ?
C3 H3 0.9500 . ?
C4 C5 1.419(10) . ?
C4 H4 0.9500 . ?
C5 C9 1.402(9) . ?
C5 C6 1.406(10) . ?
C6 C7 1.367(10) . ?
C6 H6 0.9500 . ?
C7 C8 1.405(10) . ?
C7 H7 0.9500 . ?
C8 H8 0.9500 . ?
C10 C11 1.516(9) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.507(10) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 C15 1.530(9) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 C17 1.506(9) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
O4 H4A 0.81(10) . ?
O4 H4B 0.85(9) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 Pd1 N2 83.1(2) . . ?
N1 Pd1 O2 176.4(2) . . ?
N2 Pd1 O2 94.3(2) . . ?
N1 Pd1 N3 83.9(2) . . ?
N2 Pd1 N3 166.8(2) . . ?
O2 Pd1 N3 98.79(19) . . ?
C16 O2 Pd1 119.0(4) . . ?
C10 N1 C1 125.9(6) . . ?
C10 N1 Pd1 119.4(4) . . ?
C1 N1 Pd1 114.7(4) . . ?
C8 N2 C9 119.1(6) . . ?
C8 N2 Pd1 129.3(5) . . ?
C9 N2 Pd1 111.6(4) . . ?
C12 N3 C14 111.0(5) . . ?
C12 N3 C11 112.2(5) . . ?
C14 N3 C11 108.6(5) . . ?
C12 N3 Pd1 113.2(4) . . ?
C14 N3 Pd1 105.5(4) . . ?
C11 N3 Pd1 106.0(4) . . ?
C2 C1 N1 127.9(6) . . ?
C2 C1 C9 118.5(6) . . ?
N1 C1 C9 113.5(6) . . ?
C1 C2 C3 120.1(7) . . ?
C1 C2 H2 120.0 . . ?
C3 C2 H2 120.0 . . ?
C4 C3 C2 122.3(7) . . ?
C4 C3 H3 118.8 . . ?
C2 C3 H3 118.8 . . ?
C3 C4 C5 119.6(6) . . ?
C3 C4 H4 120.2 . . ?
C5 C4 H4 120.2 . . ?
C9 C5 C6 116.9(7) . . ?
C9 C5 C4 118.6(6) . . ?
C6 C5 C4 124.5(6) . . ?
C7 C6 C5 120.8(7) . . ?
C7 C6 H6 119.6 . . ?
C5 C6 H6 119.6 . . ?
C6 C7 C8 118.7(7) . . ?
C6 C7 H7 120.7 . . ?
C8 C7 H7 120.7 . . ?
N2 C8 C7 122.5(7) . . ?
N2 C8 H8 118.8 . . ?
C7 C8 H8 118.8 . . ?
N2 C9 C5 122.0(6) . . ?
N2 C9 C1 117.0(6) . . ?
C5 C9 C1 121.0(6) . . ?
O1 C10 N1 128.9(6) . . ?
O1 C10 C11 119.2(6) . . ?
N1 C10 C11 111.9(6) . . ?
N3 C11 C10 114.4(5) . . ?
N3 C11 H11A 108.7 . . ?
C10 C11 H11A 108.7 . . ?
N3 C11 H11B 108.7 . . ?
C10 C11 H11B 108.7 . . ?
H11A C11 H11B 107.6 . . ?
N3 C12 C13 112.5(5) . . ?
N3 C12 H12A 109.1 . . ?
C13 C12 H12A 109.1 . . ?
N3 C12 H12B 109.1 . . ?
C13 C12 H12B 109.1 . . ?
H12A C12 H12B 107.8 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N3 C14 C15 114.8(6) . . ?
N3 C14 H14A 108.6 . . ?
C15 C14 H14A 108.6 . . ?
N3 C14 H14B 108.6 . . ?
C15 C14 H14B 108.6 . . ?
H14A C14 H14B 107.6 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
O3 C16 O2 124.3(6) . . ?
O3 C16 C17 121.1(7) . . ?
O2 C16 C17 114.5(6) . . ?
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 . . ?
H4A O4 H4B 108(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
C10 N1 C1 C2 0.2(11) . . . . ?
Pd1 N1 C1 C2 -179.0(6) . . . . ?
C10 N1 C1 C9 177.2(6) . . . . ?
Pd1 N1 C1 C9 -2.0(7) . . . . ?
N1 C1 C2 C3 178.0(6) . . . . ?
C9 C1 C2 C3 1.0(10) . . . . ?
C1 C2 C3 C4 -0.2(11) . . . . ?
C2 C3 C4 C5 -0.1(11) . . . . ?
C3 C4 C5 C9 -0.3(11) . . . . ?
C3 C4 C5 C6 -178.0(7) . . . . ?
C9 C5 C6 C7 1.4(11) . . . . ?
C4 C5 C6 C7 179.1(7) . . . . ?
C5 C6 C7 C8 -1.5(11) . . . . ?
C9 N2 C8 C7 -0.7(10) . . . . ?
Pd1 N2 C8 C7 179.8(5) . . . . ?
C6 C7 C8 N2 1.1(11) . . . . ?
C8 N2 C9 C5 0.6(10) . . . . ?
Pd1 N2 C9 C5 -179.8(5) . . . . ?
C8 N2 C9 C1 -179.4(6) . . . . ?
Pd1 N2 C9 C1 0.2(7) . . . . ?
C6 C5 C9 N2 -1.0(10) . . . . ?
C4 C5 C9 N2 -178.8(6) . . . . ?
C6 C5 C9 C1 179.0(6) . . . . ?
C4 C5 C9 C1 1.2(10) . . . . ?
C2 C1 C9 N2 178.5(6) . . . . ?
N1 C1 C9 N2 1.1(9) . . . . ?
C2 C1 C9 C5 -1.5(10) . . . . ?
N1 C1 C9 C5 -178.9(6) . . . . ?
C1 N1 C10 O1 5.2(11) . . . . ?
Pd1 N1 C10 O1 -175.6(6) . . . . ?
C1 N1 C10 C11 -172.0(6) . . . . ?
Pd1 N1 C10 C11 7.2(7) . . . . ?
C12 N3 C11 C10 146.7(6) . . . . ?
C14 N3 C11 C10 -90.2(6) . . . . ?
Pd1 N3 C11 C10 22.7(6) . . . . ?
O1 C10 C11 N3 162.0(6) . . . . ?
N1 C10 C11 N3 -20.6(8) . . . . ?
C14 N3 C12 C13 169.6(6) . . . . ?
C11 N3 C12 C13 -68.6(7) . . . . ?
Pd1 N3 C12 C13 51.3(7) . . . . ?
C12 N3 C14 C15 52.4(8) . . . . ?
C11 N3 C14 C15 -71.5(7) . . . . ?
Pd1 N3 C14 C15 175.2(5) . . . . ?
Pd1 O2 C16 O3 -14.9(9) . . . . ?
Pd1 O2 C16 C17 163.6(4) . . . . ?

_refine_diff_density_max         0.742
_refine_diff_density_min         -1.823
_refine_diff_density_rms         0.123

_shelxl_version_number           2013-3


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_solvent_exptl_crystal_recrystallization_method toluene-diethylether
####################################################################### 
# 
# 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_NNNPdCl_0m
_database_code_depnum_ccdc_archive 'CCDC 1487196'
_audit_update_record             
;
2016-06-22 deposited with the CCDC.
2017-03-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H18 Cl N3 O Pd'
_chemical_formula_sum            'C15 H18 Cl N3 O Pd'
_chemical_formula_weight         398.17

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, 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                   14.7945(6)
_cell_length_b                   13.1480(5)
_cell_length_c                   16.0956(7)
_cell_angle_alpha                90
_cell_angle_beta                 102.202(2)
_cell_angle_gamma                90
_cell_volume                     3060.2(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9991
_cell_measurement_theta_min      2.30
_cell_measurement_theta_max      31.61

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            YELLOW
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.728
_exptl_crystal_F_000             1600
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.460
_exptl_crystal_size_mid          0.400
_exptl_crystal_size_min          0.320
_exptl_absorpt_coefficient_mu    1.389
_shelx_estimated_absorpt_T_min   0.567
_shelx_estimated_absorpt_T_max   0.665
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.5675
_exptl_absorpt_correction_T_max  0.6649
_exptl_absorpt_process_details   SADABS,(BRUKER,2006)

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150(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 APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            20254
_diffrn_reflns_av_unetI/netI     0.0101
_diffrn_reflns_av_R_equivalents  0.0179
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.093
_diffrn_reflns_theta_max         24.995
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.975
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.975
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.975
_reflns_number_total             2696
_reflns_number_gt                2641
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0143P)²+7.7246P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2696
_refine_ls_number_parameters     192
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0187
_refine_ls_R_factor_gt           0.0181
_refine_ls_wR_factor_ref         0.0423
_refine_ls_wR_factor_gt          0.0420
_refine_ls_goodness_of_fit_ref   1.101
_refine_ls_restrained_S_all      1.101
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Pd1 Pd 0.22478(2) 0.79625(2) 0.26276(2) 0.01530(6) Uani 1 1 d . . . . .
Cl1 Cl 0.10167(3) 0.85840(4) 0.16228(3) 0.02462(12) Uani 1 1 d . . . . .
O1 O 0.46570(10) 0.65386(12) 0.36275(10) 0.0239(3) Uani 1 1 d . . . . .
N1 N 0.33388(11) 0.75230(13) 0.34571(11) 0.0185(4) Uani 1 1 d . . . . .
N2 N 0.19800(11) 0.87150(12) 0.36429(11) 0.0164(3) Uani 1 1 d . . . . .
N3 N 0.27762(12) 0.70647(13) 0.17853(11) 0.0190(4) Uani 1 1 d . . . . .
C1 C 0.34448(14) 0.79642(15) 0.42655(13) 0.0177(4) Uani 1 1 d . . . . .
C2 C 0.41604(15) 0.78259(16) 0.49628(14) 0.0221(5) Uani 1 1 d . . . . .
H2 H 0.4676 0.7415 0.4918 0.026 Uiso 1 1 calc R U . . .
C3 C 0.41203(15) 0.82968(17) 0.57389(14) 0.0250(5) Uani 1 1 d . . . . .
H3 H 0.4617 0.8199 0.6213 0.030 Uiso 1 1 calc R U . . .
C4 C 0.33887(16) 0.88918(17) 0.58327(14) 0.0251(5) Uani 1 1 d . . . . .
H4 H 0.3382 0.9196 0.6367 0.030 Uiso 1 1 calc R U . . .
C5 C 0.26421(15) 0.90530(15) 0.51352(13) 0.0201(4) Uani 1 1 d . . . . .
C6 C 0.18417(16) 0.96255(16) 0.51749(14) 0.0236(5) Uani 1 1 d . . . . .
H6 H 0.1787 0.9945 0.5691 0.028 Uiso 1 1 calc R U . . .
C7 C 0.11494(15) 0.97172(16) 0.44705(14) 0.0229(5) Uani 1 1 d . . . . .
H7 H 0.0609 1.0096 0.4496 0.028 Uiso 1 1 calc R U . . .
C8 C 0.12394(14) 0.92491(15) 0.37066(14) 0.0190(4) Uani 1 1 d . . . . .
H8 H 0.0752 0.9319 0.3220 0.023 Uiso 1 1 calc R U . . .
C9 C 0.26857(14) 0.85929(15) 0.43517(13) 0.0169(4) Uani 1 1 d . . . . .
C10 C 0.39196(14) 0.68535(15) 0.32063(13) 0.0184(4) Uani 1 1 d . . . . .
C11 C 0.35500(14) 0.64460(16) 0.23150(13) 0.0203(4) Uani 1 1 d . . . . .
H11A H 0.4067 0.6413 0.2013 0.024 Uiso 1 1 calc R U . . .
H11B H 0.3325 0.5743 0.2361 0.024 Uiso 1 1 calc R U . . .
C12 C 0.31490(16) 0.77111(17) 0.11673(14) 0.0247(5) Uani 1 1 d . . . . .
H12A H 0.2630 0.8089 0.0811 0.030 Uiso 1 1 calc R U . . .
H12B H 0.3414 0.7261 0.0787 0.030 Uiso 1 1 calc R U . . .
C13 C 0.38813(17) 0.84652(18) 0.15770(16) 0.0303(5) Uani 1 1 d . . . . .
H13A H 0.3629 0.8912 0.1960 0.045 Uiso 1 1 calc R U . . .
H13B H 0.4072 0.8875 0.1135 0.045 Uiso 1 1 calc R U . . .
H13C H 0.4417 0.8098 0.1902 0.045 Uiso 1 1 calc R U . . .
C14 C 0.20597(15) 0.63798(17) 0.12663(14) 0.0249(5) Uani 1 1 d . . . . .
H14A H 0.2370 0.5919 0.0928 0.030 Uiso 1 1 calc R U . . .
H14B H 0.1618 0.6803 0.0862 0.030 Uiso 1 1 calc R U . . .
C15 C 0.15218(15) 0.57435(18) 0.17757(15) 0.0286(5) Uani 1 1 d . . . . .
H15A H 0.1947 0.5295 0.2159 0.043 Uiso 1 1 calc R U . . .
H15B H 0.1064 0.5332 0.1389 0.043 Uiso 1 1 calc R U . . .
H15C H 0.1205 0.6191 0.2110 0.043 Uiso 1 1 calc R U . . .


_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 1.9521(17) . ?
Pd1 N2 2.0200(17) . ?
Pd1 N3 2.0713(17) . ?
Pd1 Cl1 2.3142(5) . ?
O1 C10 1.228(3) . ?
N1 C10 1.350(3) . ?
N1 C1 1.403(3) . ?
N2 C8 1.324(3) . ?
N2 C9 1.383(3) . ?
N3 C12 1.499(3) . ?
N3 C14 1.503(3) . ?
N3 C11 1.512(3) . ?
C1 C2 1.383(3) . ?
C1 C9 1.425(3) . ?
C2 C3 1.407(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.370(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.415(3) . ?
C4 H4 0.9500 . ?
C5 C9 1.412(3) . ?
C5 C6 1.416(3) . ?
C6 C7 1.363(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.406(3) . ?
C7 H7 0.9500 . ?
C8 H8 0.9500 . ?
C10 C11 1.521(3) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.513(3) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 C15 1.510(3) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 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
N1 Pd1 N2 82.35(7) . . ?
N1 Pd1 N3 84.67(7) . . ?
N2 Pd1 N3 166.99(7) . . ?
N1 Pd1 Cl1 175.82(5) . . ?
N2 Pd1 Cl1 97.61(5) . . ?
N3 Pd1 Cl1 95.40(5) . . ?
C10 N1 C1 126.40(18) . . ?
C10 N1 Pd1 118.36(14) . . ?
C1 N1 Pd1 115.23(13) . . ?
C8 N2 C9 119.38(18) . . ?
C8 N2 Pd1 129.03(14) . . ?
C9 N2 Pd1 111.55(13) . . ?
C12 N3 C14 106.62(16) . . ?
C12 N3 C11 109.77(16) . . ?
C14 N3 C11 110.61(16) . . ?
C12 N3 Pd1 110.73(13) . . ?
C14 N3 Pd1 112.70(13) . . ?
C11 N3 Pd1 106.44(12) . . ?
C2 C1 N1 127.95(19) . . ?
C2 C1 C9 118.78(19) . . ?
N1 C1 C9 113.22(18) . . ?
C1 C2 C3 119.6(2) . . ?
C1 C2 H2 120.2 . . ?
C3 C2 H2 120.2 . . ?
C4 C3 C2 122.1(2) . . ?
C4 C3 H3 118.9 . . ?
C2 C3 H3 118.9 . . ?
C3 C4 C5 120.1(2) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
C9 C5 C4 117.97(19) . . ?
C9 C5 C6 117.68(19) . . ?
C4 C5 C6 124.3(2) . . ?
C7 C6 C5 119.9(2) . . ?
C7 C6 H6 120.1 . . ?
C5 C6 H6 120.1 . . ?
C6 C7 C8 119.68(19) . . ?
C6 C7 H7 120.2 . . ?
C8 C7 H7 120.2 . . ?
N2 C8 C7 122.2(2) . . ?
N2 C8 H8 118.9 . . ?
C7 C8 H8 118.9 . . ?
N2 C9 C5 121.17(18) . . ?
N2 C9 C1 117.39(18) . . ?
C5 C9 C1 121.41(19) . . ?
O1 C10 N1 127.0(2) . . ?
O1 C10 C11 120.15(18) . . ?
N1 C10 C11 112.77(17) . . ?
N3 C11 C10 114.88(16) . . ?
N3 C11 H11A 108.5 . . ?
C10 C11 H11A 108.5 . . ?
N3 C11 H11B 108.5 . . ?
C10 C11 H11B 108.5 . . ?
H11A C11 H11B 107.5 . . ?
N3 C12 C13 114.34(18) . . ?
N3 C12 H12A 108.7 . . ?
C13 C12 H12A 108.7 . . ?
N3 C12 H12B 108.7 . . ?
C13 C12 H12B 108.7 . . ?
H12A C12 H12B 107.6 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N3 C14 C15 114.89(18) . . ?
N3 C14 H14A 108.5 . . ?
C15 C14 H14A 108.5 . . ?
N3 C14 H14B 108.5 . . ?
C15 C14 H14B 108.5 . . ?
H14A C14 H14B 107.5 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 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
C10 N1 C1 C2 1.2(3) . . . . ?
Pd1 N1 C1 C2 -177.52(17) . . . . ?
C10 N1 C1 C9 -176.21(18) . . . . ?
Pd1 N1 C1 C9 5.1(2) . . . . ?
N1 C1 C2 C3 -176.7(2) . . . . ?
C9 C1 C2 C3 0.6(3) . . . . ?
C1 C2 C3 C4 0.2(3) . . . . ?
C2 C3 C4 C5 -0.2(3) . . . . ?
C3 C4 C5 C9 -0.6(3) . . . . ?
C3 C4 C5 C6 177.8(2) . . . . ?
C9 C5 C6 C7 -0.1(3) . . . . ?
C4 C5 C6 C7 -178.5(2) . . . . ?
C5 C6 C7 C8 -0.6(3) . . . . ?
C9 N2 C8 C7 1.2(3) . . . . ?
Pd1 N2 C8 C7 178.80(14) . . . . ?
C6 C7 C8 N2 0.0(3) . . . . ?
C8 N2 C9 C5 -1.9(3) . . . . ?
Pd1 N2 C9 C5 -179.88(15) . . . . ?
C8 N2 C9 C1 176.50(17) . . . . ?
Pd1 N2 C9 C1 -1.5(2) . . . . ?
C4 C5 C9 N2 179.83(18) . . . . ?
C6 C5 C9 N2 1.3(3) . . . . ?
C4 C5 C9 C1 1.5(3) . . . . ?
C6 C5 C9 C1 -176.99(18) . . . . ?
C2 C1 C9 N2 -179.90(18) . . . . ?
N1 C1 C9 N2 -2.2(3) . . . . ?
C2 C1 C9 C5 -1.5(3) . . . . ?
N1 C1 C9 C5 176.15(18) . . . . ?
C1 N1 C10 O1 -2.7(3) . . . . ?
Pd1 N1 C10 O1 175.93(16) . . . . ?
C1 N1 C10 C11 174.27(18) . . . . ?
Pd1 N1 C10 C11 -7.0(2) . . . . ?
C12 N3 C11 C10 101.8(2) . . . . ?
C14 N3 C11 C10 -140.82(18) . . . . ?
Pd1 N3 C11 C10 -18.1(2) . . . . ?
O1 C10 C11 N3 -165.51(18) . . . . ?
N1 C10 C11 N3 17.2(2) . . . . ?
C14 N3 C12 C13 179.45(18) . . . . ?
C11 N3 C12 C13 -60.7(2) . . . . ?
Pd1 N3 C12 C13 56.5(2) . . . . ?
C12 N3 C14 C15 -173.51(18) . . . . ?
C11 N3 C14 C15 67.2(2) . . . . ?
Pd1 N3 C14 C15 -51.8(2) . . . . ?

_refine_diff_density_max         0.583
_refine_diff_density_min         -0.397
_refine_diff_density_rms         0.060

_shelxl_version_number           2013-3


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_solvent_exptl_crystal_recrystallization_method toluene-diethylether
