# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_4a
_database_code_depnum_ccdc_archive 'CCDC 1038592'
_audit_update_record             
;
2014-12-10 deposited with the CCDC.
2016-06-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H15 Cl N2 Pd'
_chemical_formula_sum            'C14 H15 Cl N2 Pd'
_chemical_formula_weight         353.13

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'
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           7
_space_group_name_H-M_alt        'P c'
_space_group_name_Hall           'P -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'

_cell_length_a                   9.4647(7)
_cell_length_b                   12.7252(9)
_cell_length_c                   11.5908(8)
_cell_angle_alpha                90
_cell_angle_beta                 108.6240(10)
_cell_angle_gamma                90
_cell_volume                     1322.90(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    29218
_cell_measurement_theta_min      2.8
_cell_measurement_theta_max      27.5

_exptl_crystal_description       Block
_exptl_crystal_colour            'Pale Yellow'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.773
_exptl_crystal_F_000             704
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.090
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    1.587
_shelx_estimated_absorpt_T_min   0.870
_shelx_estimated_absorpt_T_max   0.939
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.821
_exptl_absorpt_process_details   
;
CrystalClear-SM Expert 3.1 b27 (Rigaku, 2013)
;
_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_radiation_collimation    'Confocal mirrors, VHF Varimax'
_diffrn_source                   'Rotating Anode'
_diffrn_source_power             2.475
_diffrn_source_voltage           45.0
_diffrn_source_current           55.0
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            'Rigaku HG Saturn724+ (2x2 bin mode)'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measurement_device       'four-circle κ diffractometer'
_diffrn_measurement_device_type  'Rigaku AFC12 (Right)'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_measurement_specimen_support 'MiTeGen MicroMesh'
_diffrn_reflns_number            17067
_diffrn_reflns_av_unetI/netI     0.0241
_diffrn_reflns_av_R_equivalents  0.0337
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.910
_diffrn_reflns_theta_max         27.480
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.885
_diffrn_reflns_point_group_measured_fraction_full 0.907
_reflns_number_total             5364
_reflns_number_gt                5345
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.769
_reflns_Friedel_fraction_max     0.771
_reflns_Friedel_fraction_full    0.818

_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       
;
CrystalClear-SM Expert 3.1 b27 (Rigaku, 2013)
;
_computing_cell_refinement       
;
CrystalClear-SM Expert 3.1 b27 (Rigaku, 2013)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 3.1 b27 (Rigaku, 2013)
;
_computing_structure_solution    'SUPERFLIP (Palatinus & Chapuis, 2007)'
_computing_structure_refinement  'SHELXL-2012 (Sheldrick, 2012)'
_computing_molecular_graphics    
'OLEX2 (Dolomanov, Bourhis, Gildea, Howard & Puschmann, 2009)'
_computing_publication_material  'WINGX (Farrugia, 1998)'

_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)+(0.0594P)²+2.1099P] 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_abs_structure_details 
;
 Flack x determined using 2305 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.034(16)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         5364
_refine_ls_number_parameters     329
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0332
_refine_ls_R_factor_gt           0.0331
_refine_ls_wR_factor_ref         0.0884
_refine_ls_wR_factor_gt          0.0883
_refine_ls_goodness_of_fit_ref   1.097
_refine_ls_restrained_S_all      1.097
_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
C1 C -0.0362(8) 0.2368(6) 1.0499(7) 0.0214(13) Uani 1 1 d . . . . .
H1 H 0.0654 0.2280 1.0973 0.026 Uiso 1 1 calc R U . . .
C2 C -0.1445(9) 0.1956(6) 1.0931(7) 0.0247(14) Uani 1 1 d . . . . .
H2 H -0.1178 0.1591 1.1686 0.030 Uiso 1 1 calc R U . . .
C3 C -0.2934(8) 0.2084(6) 1.0243(7) 0.0257(15) Uani 1 1 d . . . . .
H3 H -0.3700 0.1813 1.0525 0.031 Uiso 1 1 calc R U . . .
C4 C -0.3288(7) 0.2605(6) 0.9150(7) 0.0226(13) Uani 1 1 d . . . . .
H4 H -0.4301 0.2695 0.8669 0.027 Uiso 1 1 calc R U . . .
C5 C -0.2149(7) 0.3004(5) 0.8751(6) 0.0175(12) Uani 1 1 d . . . . .
C6 C -0.2352(7) 0.3615(5) 0.7636(7) 0.0164(12) Uani 1 1 d . . . . .
C7 C -0.3689(7) 0.3892(6) 0.6741(7) 0.0209(13) Uani 1 1 d . . . . .
H7 H -0.4618 0.3671 0.6806 0.025 Uiso 1 1 calc R U . . .
C8 C -0.3638(8) 0.4491(6) 0.5761(7) 0.0256(14) Uani 1 1 d . . . . .
H8 H -0.4546 0.4703 0.5173 0.031 Uiso 1 1 calc R U . . .
C9 C -0.2290(8) 0.4794(6) 0.5612(7) 0.0238(14) Uani 1 1 d . . . . .
H9 H -0.2285 0.5192 0.4920 0.029 Uiso 1 1 calc R U . . .
C10 C -0.0945(7) 0.4508(5) 0.6490(6) 0.0177(12) Uani 1 1 d . . . . .
C11 C -0.1003(7) 0.3950(5) 0.7493(6) 0.0160(12) Uani 1 1 d . . . . .
C12 C 0.0599(8) 0.4669(6) 0.6407(6) 0.0201(13) Uani 1 1 d . . . . .
H12A H 0.0670 0.5366 0.6052 0.024 Uiso 1 1 calc R U . . .
H12B H 0.0820 0.4123 0.5880 0.024 Uiso 1 1 calc R U . . .
C13 C 0.1844(8) 0.5657(5) 0.8281(8) 0.0253(15) Uani 1 1 d . . . . .
H13A H 0.2437 0.5596 0.9142 0.038 Uiso 1 1 calc R U . . .
H13B H 0.0851 0.5928 0.8211 0.038 Uiso 1 1 calc R U . . .
H13C H 0.2339 0.6141 0.7875 0.038 Uiso 1 1 calc R U . . .
C14 C 0.3163(7) 0.4298(6) 0.7593(7) 0.0225(14) Uani 1 1 d . . . . .
H14A H 0.3499 0.4839 0.7138 0.034 Uiso 1 1 calc R U . . .
H14B H 0.3078 0.3624 0.7167 0.034 Uiso 1 1 calc R U . . .
H14C H 0.3887 0.4233 0.8411 0.034 Uiso 1 1 calc R U . . .
Cl1 Cl 0.30973(18) 0.32300(15) 1.03896(16) 0.0259(4) Uani 1 1 d . . . . .
N1 N -0.0679(6) 0.2884(4) 0.9444(5) 0.0166(11) Uani 1 1 d . . . . .
N2 N 0.1700(6) 0.4595(4) 0.7687(5) 0.0187(11) Uani 1 1 d . . . . .
Pd1 Pd 0.08208(4) 0.36045(4) 0.87431(4) 0.01386(12) Uani 1 1 d . . . . .
C101 C -0.1466(8) 0.2804(6) 0.3937(7) 0.0252(14) Uani 1 1 d . . . . .
H101 H -0.0561 0.3021 0.3820 0.030 Uiso 1 1 calc R U . . .
C102 C -0.2810(10) 0.3119(7) 0.3102(7) 0.0302(16) Uani 1 1 d . . . . .
H102 H -0.2820 0.3545 0.2426 0.036 Uiso 1 1 calc R U . . .
C103 C -0.4121(9) 0.2811(7) 0.3264(7) 0.0313(17) Uani 1 1 d . . . . .
H103 H -0.5048 0.3023 0.2702 0.038 Uiso 1 1 calc R U . . .
C104 C -0.4087(8) 0.2188(6) 0.4254(7) 0.0237(14) Uani 1 1 d . . . . .
H104 H -0.4989 0.1960 0.4369 0.028 Uiso 1 1 calc R U . . .
C105 C -0.2712(7) 0.1897(5) 0.5080(6) 0.0179(12) Uani 1 1 d . . . . .
C106 C -0.2472(7) 0.1252(5) 0.6178(6) 0.0163(12) Uani 1 1 d . . . . .
C107 C -0.3574(7) 0.0793(6) 0.6593(7) 0.0221(14) Uani 1 1 d . . . . .
H107 H -0.4601 0.0863 0.6140 0.027 Uiso 1 1 calc R U . . .
C108 C -0.3130(7) 0.0240(6) 0.7668(7) 0.0231(14) Uani 1 1 d . . . . .
H108 H -0.3869 -0.0070 0.7954 0.028 Uiso 1 1 calc R U . . .
C109 C -0.1623(8) 0.0118(5) 0.8357(7) 0.0211(13) Uani 1 1 d . . . . .
H109 H -0.1350 -0.0258 0.9104 0.025 Uiso 1 1 calc R U . . .
C110 C -0.0528(7) 0.0554(5) 0.7935(6) 0.0166(12) Uani 1 1 d . . . . .
C111 C -0.0997(7) 0.1105(5) 0.6845(6) 0.0169(12) Uani 1 1 d . . . . .
C112 C 0.1157(7) 0.0569(6) 0.8577(7) 0.0230(14) Uani 1 1 d . . . . .
H11A H 0.1423 0.1143 0.9184 0.028 Uiso 1 1 calc R U . . .
H11B H 0.1484 -0.0106 0.9005 0.028 Uiso 1 1 calc R U . . .
C113 C 0.2099(9) -0.0292(6) 0.7091(7) 0.0257(14) Uani 1 1 d . . . . .
H11C H 0.2598 -0.0184 0.6478 0.039 Uiso 1 1 calc R U . . .
H11D H 0.1121 -0.0613 0.6707 0.039 Uiso 1 1 calc R U . . .
H11E H 0.2707 -0.0756 0.7734 0.039 Uiso 1 1 calc R U . . .
C114 C 0.3402(7) 0.1199(6) 0.8233(7) 0.0247(14) Uani 1 1 d . . . . .
H11F H 0.3989 0.0720 0.8867 0.037 Uiso 1 1 calc R U . . .
H11G H 0.3288 0.1874 0.8602 0.037 Uiso 1 1 calc R U . . .
H11H H 0.3914 0.1310 0.7630 0.037 Uiso 1 1 calc R U . . .
Cl11 Cl 0.23443(17) 0.21289(13) 0.52198(16) 0.0221(3) Uani 1 1 d . . . . .
N101 N -0.1406(6) 0.2199(4) 0.4908(5) 0.0166(10) Uani 1 1 d . . . . .
N102 N 0.1906(6) 0.0735(4) 0.7628(5) 0.0159(10) Uani 1 1 d . . . . .
Pd11 Pd 0.04966(4) 0.16255(3) 0.61774(4) 0.01345(12) 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
C1 N1 1.335(9) . ?
C1 C2 1.380(10) . ?
C1 H1 0.9500 . ?
C2 C3 1.389(11) . ?
C2 H2 0.9500 . ?
C3 C4 1.373(11) . ?
C3 H3 0.9500 . ?
C4 C5 1.397(9) . ?
C4 H4 0.9500 . ?
C5 N1 1.375(8) . ?
C5 C6 1.467(10) . ?
C6 C7 1.401(9) . ?
C6 C11 1.405(8) . ?
C7 C8 1.380(11) . ?
C7 H7 0.9500 . ?
C8 C9 1.396(10) . ?
C8 H8 0.9500 . ?
C9 C10 1.401(9) . ?
C9 H9 0.9500 . ?
C10 C11 1.378(9) . ?
C10 C12 1.508(9) . ?
C11 Pd1 1.917(6) . ?
C12 N2 1.520(9) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 N2 1.503(8) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 N2 1.474(8) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
Cl1 Pd1 2.4260(17) . ?
N1 Pd1 2.062(5) . ?
N2 Pd1 2.105(6) . ?
C101 N101 1.350(9) . ?
C101 C102 1.389(11) . ?
C101 H101 0.9500 . ?
C102 C103 1.370(12) . ?
C102 H102 0.9500 . ?
C103 C104 1.386(11) . ?
C103 H103 0.9500 . ?
C104 C105 1.396(9) . ?
C104 H104 0.9500 . ?
C105 N101 1.369(8) . ?
C105 C106 1.470(10) . ?
C106 C111 1.376(9) . ?
C106 C107 1.407(9) . ?
C107 C108 1.375(10) . ?
C107 H107 0.9500 . ?
C108 C109 1.404(10) . ?
C108 H108 0.9500 . ?
C109 C110 1.395(9) . ?
C109 H109 0.9500 . ?
C110 C111 1.388(9) . ?
C110 C112 1.529(9) . ?
C111 Pd11 1.933(6) . ?
C112 N102 1.503(9) . ?
C112 H11A 0.9900 . ?
C112 H11B 0.9900 . ?
C113 N102 1.483(8) . ?
C113 H11C 0.9800 . ?
C113 H11D 0.9800 . ?
C113 H11E 0.9800 . ?
C114 N102 1.487(8) . ?
C114 H11F 0.9800 . ?
C114 H11G 0.9800 . ?
C114 H11H 0.9800 . ?
Cl11 Pd11 2.4373(16) . ?
N101 Pd11 2.061(5) . ?
N102 Pd11 2.111(5) . ?

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 C1 C2 123.0(7) . . ?
N1 C1 H1 118.5 . . ?
C2 C1 H1 118.5 . . ?
C1 C2 C3 118.8(7) . . ?
C1 C2 H2 120.6 . . ?
C3 C2 H2 120.6 . . ?
C4 C3 C2 119.4(6) . . ?
C4 C3 H3 120.3 . . ?
C2 C3 H3 120.3 . . ?
C3 C4 C5 119.6(7) . . ?
C3 C4 H4 120.2 . . ?
C5 C4 H4 120.2 . . ?
N1 C5 C4 120.7(6) . . ?
N1 C5 C6 113.4(5) . . ?
C4 C5 C6 125.9(6) . . ?
C7 C6 C11 118.4(6) . . ?
C7 C6 C5 128.3(6) . . ?
C11 C6 C5 113.4(6) . . ?
C8 C7 C6 119.2(6) . . ?
C8 C7 H7 120.4 . . ?
C6 C7 H7 120.4 . . ?
C7 C8 C9 121.9(6) . . ?
C7 C8 H8 119.1 . . ?
C9 C8 H8 119.1 . . ?
C8 C9 C10 119.5(6) . . ?
C8 C9 H9 120.2 . . ?
C10 C9 H9 120.2 . . ?
C11 C10 C9 118.3(6) . . ?
C11 C10 C12 115.1(6) . . ?
C9 C10 C12 126.3(6) . . ?
C10 C11 C6 122.6(6) . . ?
C10 C11 Pd1 119.1(5) . . ?
C6 C11 Pd1 118.3(5) . . ?
C10 C12 N2 107.8(5) . . ?
C10 C12 H12A 110.2 . . ?
N2 C12 H12A 110.2 . . ?
C10 C12 H12B 110.2 . . ?
N2 C12 H12B 110.2 . . ?
H12A C12 H12B 108.5 . . ?
N2 C13 H13A 109.5 . . ?
N2 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
N2 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N2 C14 H14A 109.5 . . ?
N2 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
N2 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C1 N1 C5 118.6(6) . . ?
C1 N1 Pd1 126.7(5) . . ?
C5 N1 Pd1 114.6(4) . . ?
C14 N2 C13 108.3(5) . . ?
C14 N2 C12 108.1(5) . . ?
C13 N2 C12 109.0(5) . . ?
C14 N2 Pd1 116.4(4) . . ?
C13 N2 Pd1 105.5(4) . . ?
C12 N2 Pd1 109.3(4) . . ?
C11 Pd1 N1 80.4(3) . . ?
C11 Pd1 N2 81.4(2) . . ?
N1 Pd1 N2 160.9(2) . . ?
C11 Pd1 Cl1 177.18(19) . . ?
N1 Pd1 Cl1 98.80(17) . . ?
N2 Pd1 Cl1 99.12(16) . . ?
N101 C101 C102 122.1(7) . . ?
N101 C101 H101 119.0 . . ?
C102 C101 H101 119.0 . . ?
C103 C102 C101 119.4(8) . . ?
C103 C102 H102 120.3 . . ?
C101 C102 H102 120.3 . . ?
C102 C103 C104 119.6(7) . . ?
C102 C103 H103 120.2 . . ?
C104 C103 H103 120.2 . . ?
C103 C104 C105 119.3(7) . . ?
C103 C104 H104 120.4 . . ?
C105 C104 H104 120.4 . . ?
N101 C105 C104 120.9(7) . . ?
N101 C105 C106 112.7(6) . . ?
C104 C105 C106 126.4(6) . . ?
C111 C106 C107 118.7(6) . . ?
C111 C106 C105 114.3(6) . . ?
C107 C106 C105 127.0(6) . . ?
C108 C107 C106 118.5(6) . . ?
C108 C107 H107 120.7 . . ?
C106 C107 H107 120.7 . . ?
C107 C108 C109 122.2(6) . . ?
C107 C108 H108 118.9 . . ?
C109 C108 H108 118.9 . . ?
C110 C109 C108 119.4(6) . . ?
C110 C109 H109 120.3 . . ?
C108 C109 H109 120.3 . . ?
C111 C110 C109 117.6(6) . . ?
C111 C110 C112 114.7(6) . . ?
C109 C110 C112 127.6(6) . . ?
C106 C111 C110 123.6(6) . . ?
C106 C111 Pd11 118.0(5) . . ?
C110 C111 Pd11 118.4(5) . . ?
N102 C112 C110 107.9(5) . . ?
N102 C112 H11A 110.1 . . ?
C110 C112 H11A 110.1 . . ?
N102 C112 H11B 110.1 . . ?
C110 C112 H11B 110.1 . . ?
H11A C112 H11B 108.4 . . ?
N102 C113 H11C 109.5 . . ?
N102 C113 H11D 109.5 . . ?
H11C C113 H11D 109.5 . . ?
N102 C113 H11E 109.5 . . ?
H11C C113 H11E 109.5 . . ?
H11D C113 H11E 109.5 . . ?
N102 C114 H11F 109.5 . . ?
N102 C114 H11G 109.5 . . ?
H11F C114 H11G 109.5 . . ?
N102 C114 H11H 109.5 . . ?
H11F C114 H11H 109.5 . . ?
H11G C114 H11H 109.5 . . ?
C101 N101 C105 118.8(6) . . ?
C101 N101 Pd11 126.3(5) . . ?
C105 N101 Pd11 114.9(4) . . ?
C113 N102 C114 108.8(5) . . ?
C113 N102 C112 109.5(6) . . ?
C114 N102 C112 108.1(5) . . ?
C113 N102 Pd11 105.7(4) . . ?
C114 N102 Pd11 115.3(5) . . ?
C112 N102 Pd11 109.4(4) . . ?
C111 Pd11 N101 79.8(3) . . ?
C111 Pd11 N102 81.6(3) . . ?
N101 Pd11 N102 160.8(2) . . ?
C111 Pd11 Cl11 174.52(19) . . ?
N101 Pd11 Cl11 99.92(16) . . ?
N102 Pd11 Cl11 98.09(16) . . ?

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
N1 C1 C2 C3 -0.1(11) . . . . ?
C1 C2 C3 C4 0.6(11) . . . . ?
C2 C3 C4 C5 -0.4(11) . . . . ?
C3 C4 C5 N1 -0.4(10) . . . . ?
C3 C4 C5 C6 -177.2(6) . . . . ?
N1 C5 C6 C7 -179.2(6) . . . . ?
C4 C5 C6 C7 -2.3(11) . . . . ?
N1 C5 C6 C11 0.5(8) . . . . ?
C4 C5 C6 C11 177.5(6) . . . . ?
C11 C6 C7 C8 -0.7(10) . . . . ?
C5 C6 C7 C8 179.0(7) . . . . ?
C6 C7 C8 C9 2.6(11) . . . . ?
C7 C8 C9 C10 -1.6(11) . . . . ?
C8 C9 C10 C11 -1.3(10) . . . . ?
C8 C9 C10 C12 173.0(7) . . . . ?
C9 C10 C11 C6 3.2(10) . . . . ?
C12 C10 C11 C6 -171.8(6) . . . . ?
C9 C10 C11 Pd1 -177.2(5) . . . . ?
C12 C10 C11 Pd1 7.8(8) . . . . ?
C7 C6 C11 C10 -2.2(10) . . . . ?
C5 C6 C11 C10 178.1(6) . . . . ?
C7 C6 C11 Pd1 178.2(5) . . . . ?
C5 C6 C11 Pd1 -1.6(7) . . . . ?
C11 C10 C12 N2 -24.4(8) . . . . ?
C9 C10 C12 N2 161.1(6) . . . . ?
C2 C1 N1 C5 -0.6(10) . . . . ?
C2 C1 N1 Pd1 176.4(5) . . . . ?
C4 C5 N1 C1 0.9(9) . . . . ?
C6 C5 N1 C1 178.0(6) . . . . ?
C4 C5 N1 Pd1 -176.5(5) . . . . ?
C6 C5 N1 Pd1 0.6(7) . . . . ?
C10 C12 N2 C14 156.2(5) . . . . ?
C10 C12 N2 C13 -86.3(6) . . . . ?
C10 C12 N2 Pd1 28.5(6) . . . . ?
N101 C101 C102 C103 0.0(12) . . . . ?
C101 C102 C103 C104 -0.2(12) . . . . ?
C102 C103 C104 C105 0.9(11) . . . . ?
C103 C104 C105 N101 -1.5(10) . . . . ?
C103 C104 C105 C106 179.4(7) . . . . ?
N101 C105 C106 C111 2.2(8) . . . . ?
C104 C105 C106 C111 -178.6(6) . . . . ?
N101 C105 C106 C107 -178.0(6) . . . . ?
C104 C105 C106 C107 1.1(11) . . . . ?
C111 C106 C107 C108 1.8(10) . . . . ?
C105 C106 C107 C108 -177.9(6) . . . . ?
C106 C107 C108 C109 -0.2(11) . . . . ?
C107 C108 C109 C110 -1.1(11) . . . . ?
C108 C109 C110 C111 0.8(9) . . . . ?
C108 C109 C110 C112 176.0(6) . . . . ?
C107 C106 C111 C110 -2.2(10) . . . . ?
C105 C106 C111 C110 177.6(6) . . . . ?
C107 C106 C111 Pd11 174.1(5) . . . . ?
C105 C106 C111 Pd11 -6.1(7) . . . . ?
C109 C110 C111 C106 0.9(10) . . . . ?
C112 C110 C111 C106 -174.9(6) . . . . ?
C109 C110 C111 Pd11 -175.4(5) . . . . ?
C112 C110 C111 Pd11 8.7(8) . . . . ?
C111 C110 C112 N102 -25.9(8) . . . . ?
C109 C110 C112 N102 158.8(6) . . . . ?
C102 C101 N101 C105 -0.6(10) . . . . ?
C102 C101 N101 Pd11 177.4(5) . . . . ?
C104 C105 N101 C101 1.3(10) . . . . ?
C106 C105 N101 C101 -179.4(6) . . . . ?
C104 C105 N101 Pd11 -176.9(5) . . . . ?
C106 C105 N101 Pd11 2.3(7) . . . . ?
C110 C112 N102 C113 -85.6(6) . . . . ?
C110 C112 N102 C114 156.0(6) . . . . ?
C110 C112 N102 Pd11 29.7(6) . . . . ?

_refine_diff_density_max         2.203
_refine_diff_density_min         -0.700
_refine_diff_density_rms         0.144

_shelxl_version_number           2013-3


####################################################################### 
# 
# 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_4b
_database_code_depnum_ccdc_archive 'CCDC 1038593'
_audit_update_record             
;
2014-12-10 deposited with the CCDC.
2016-06-08 downloaded from the CCDC.
;
_audit_creation_date             2014-01-13
_audit_creation_method           
;
Olex2 1.2
(compiled 2013.12.10 svn.r2850 for OlexSys, GUI svn.r4736)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C16 H19 Cl N2 Pd'
_chemical_formula_sum            'C16 H19 Cl1 N2 Pd1'
_chemical_formula_weight         381.18
_chemical_melting_point          ?
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'
Pd Pd -0.9988 1.0072 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   9.6575(7)
_cell_length_b                   11.6750(8)
_cell_length_c                   26.2578(18)
_cell_angle_alpha                90
_cell_angle_beta                 92.0790(10)
_cell_angle_gamma                90
_cell_volume                     2958.7(4)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    21260
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      2.6
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.426
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.686
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_process_details   'CrystalClear-SM Expert 3.1 b27 (Rigaku, 2013)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.711
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       Block
_exptl_crystal_F_000             1536
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.06
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0348
_diffrn_reflns_av_unetI/netI     0.0283
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            20832
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        27.500
_diffrn_reflns_theta_max         27.485
_diffrn_reflns_theta_min         2.574
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_detector_type            'Rigaku HG Saturn724+ (2x2 bin mode)'
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device       'four-circle κ diffractometer'
_diffrn_measurement_device_type  'Rigaku AFC12 (Right)'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_measurement_specimen_support 'MiTeGen MicroMesh'
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      0.081318
_diffrn_orient_matrix_UB_12      -0.010042
_diffrn_orient_matrix_UB_13      -0.063423
_diffrn_orient_matrix_UB_21      -0.022832
_diffrn_orient_matrix_UB_22      -0.080895
_diffrn_orient_matrix_UB_23      -0.016467
_diffrn_orient_matrix_UB_31      -0.020222
_diffrn_orient_matrix_UB_32      0.011826
_diffrn_orient_matrix_UB_33      -0.030059
_diffrn_radiation_collimation    0.3
_diffrn_radiation_monochromator  'Confocal mirrors, HF Varimax'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           55.0
_diffrn_source_power             2.475
_diffrn_source_target            Mo
_diffrn_source_type              'Rotating Anode'
_diffrn_source_voltage           45.0
_diffrn_special_details          
;
 ?
;
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                6135
_reflns_number_total             6748
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrystalClear-SM Expert 3.1 b27 (Rigaku, 2013)'
_computing_data_collection       'CrystalClear-SM Expert 3.1 b27 (Rigaku, 2013)'
_computing_data_reduction        'CrystalClear-SM Expert 3.1 b27 (Rigaku, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.455
_refine_diff_density_min         -0.568
_refine_diff_density_rms         0.084
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     365
_refine_ls_number_reflns         6748
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0257
_refine_ls_R_factor_gt           0.0229
_refine_ls_restrained_S_all      1.067
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0338P)²+0.7357P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0604
_refine_ls_wR_factor_ref         0.0616
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C13(H13A,H13B), C15(H15A,H15B), C112(H11A,H11B), C113(H11C,
 H11D), C115(H11H,H11I)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C7(H7), C8(H8), C9(H9), C101(H101),
 C102(H102), C103(H103), C104(H104), C107(H107), C108(H108), C109(H109)
2.c Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C16(H16A,H16B,H16C), C114(H11E,H11F,H11G), C116(H11J,
 H11K,H11L)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Pd1 Pd 0.02787(2) 0.34900(2) 0.31071(2) 0.01122(5) Uani 1 1 d . . . . .
Cl1 Cl -0.18148(5) 0.40431(4) 0.35253(2) 0.01889(10) Uani 1 1 d . . . . .
N1 N 0.16747(16) 0.46543(14) 0.34200(6) 0.0132(3) Uani 1 1 d . . . . .
N2 N -0.05675(16) 0.20552(13) 0.27153(6) 0.0130(3) Uani 1 1 d . . . . .
C1 C 0.13831(19) 0.55197(16) 0.37356(7) 0.0144(4) Uani 1 1 d . . . . .
H1 H 0.0445 0.5648 0.3817 0.017 Uiso 1 1 calc R . . . .
C2 C 0.2398(2) 0.62345(17) 0.39474(8) 0.0185(4) Uani 1 1 d . . . . .
H2 H 0.2156 0.6848 0.4165 0.022 Uiso 1 1 calc R . . . .
C3 C 0.3767(2) 0.60382(17) 0.38365(8) 0.0183(4) Uani 1 1 d . . . . .
H3 H 0.4481 0.6509 0.3981 0.022 Uiso 1 1 calc R . . . .
C4 C 0.4088(2) 0.51464(17) 0.35112(7) 0.0164(4) Uani 1 1 d . . . . .
H4 H 0.5025 0.4999 0.3435 0.020 Uiso 1 1 calc R . . . .
C5 C 0.30342(19) 0.44718(16) 0.32979(7) 0.0132(4) Uani 1 1 d . . . . .
C6 C 0.31912(19) 0.35349(16) 0.29331(7) 0.0137(4) Uani 1 1 d . . . . .
C7 C 0.4410(2) 0.31573(17) 0.27160(8) 0.0163(4) Uani 1 1 d . . . . .
H7 H 0.5275 0.3498 0.2809 0.020 Uiso 1 1 calc R . . . .
C8 C 0.43319(19) 0.22706(17) 0.23591(8) 0.0165(4) Uani 1 1 d . . . . .
H8 H 0.5156 0.2020 0.2207 0.020 Uiso 1 1 calc R . . . .
C9 C 0.3079(2) 0.17440(17) 0.22204(8) 0.0164(4) Uani 1 1 d . . . . .
H9 H 0.3055 0.1140 0.1978 0.020 Uiso 1 1 calc R . . . .
C10 C 0.18607(19) 0.21092(16) 0.24398(7) 0.0140(4) Uani 1 1 d . . . . .
C11 C 0.19359(19) 0.29990(16) 0.27900(7) 0.0133(4) Uani 1 1 d . . . . .
C12 C 0.04328(19) 0.16638(17) 0.23163(7) 0.0145(4) Uani 1 1 d . . . . .
H12A H 0.0453 0.0816 0.2305 0.017 Uiso 1 1 calc R . . . .
H12B H 0.0112 0.1946 0.1977 0.017 Uiso 1 1 calc R . . . .
C13 C -0.0765(2) 0.11119(17) 0.30952(7) 0.0160(4) Uani 1 1 d . . . . .
H13A H -0.1133 0.0429 0.2912 0.019 Uiso 1 1 calc R . . . .
H13B H -0.1468 0.1358 0.3337 0.019 Uiso 1 1 calc R . . . .
C14 C 0.0535(2) 0.07768(17) 0.33929(8) 0.0188(4) Uani 1 1 d . . . . .
H14A H 0.1239 0.0528 0.3157 0.028 Uiso 1 1 calc GR . . . .
H14B H 0.0329 0.0148 0.3626 0.028 Uiso 1 1 calc GR . . . .
H14C H 0.0884 0.1436 0.3590 0.028 Uiso 1 1 calc GR . . . .
C15 C -0.19596(18) 0.22669(17) 0.24642(7) 0.0147(4) Uani 1 1 d . . . . .
H15A H -0.2654 0.2329 0.2731 0.018 Uiso 1 1 calc R . . . .
H15B H -0.2213 0.1598 0.2248 0.018 Uiso 1 1 calc R . . . .
C16 C -0.2029(2) 0.33353(18) 0.21388(8) 0.0194(4) Uani 1 1 d . . . . .
H16A H -0.1325 0.3294 0.1880 0.029 Uiso 1 1 calc GR . . . .
H16B H -0.1857 0.4010 0.2354 0.029 Uiso 1 1 calc GR . . . .
H16C H -0.2950 0.3395 0.1971 0.029 Uiso 1 1 calc GR . . . .
Pd11 Pd 0.73640(2) 0.79754(2) 0.44697(2) 0.01245(5) Uani 1 1 d . . . . .
Cl11 Cl 0.93878(5) 0.79513(4) 0.39528(2) 0.01899(10) Uani 1 1 d . . . . .
N101 N 0.60812(16) 0.89712(14) 0.40155(6) 0.0144(3) Uani 1 1 d . . . . .
N102 N 0.81715(16) 0.69479(14) 0.50700(6) 0.0143(3) Uani 1 1 d . . . . .
C101 C 0.6421(2) 0.94384(17) 0.35701(7) 0.0170(4) Uani 1 1 d . . . . .
H101 H 0.7294 0.9261 0.3435 0.020 Uiso 1 1 calc R . . . .
C102 C 0.5537(2) 1.01710(17) 0.33018(7) 0.0186(4) Uani 1 1 d . . . . .
H102 H 0.5804 1.0497 0.2989 0.022 Uiso 1 1 calc R . . . .
C103 C 0.4260(2) 1.04221(17) 0.34950(8) 0.0192(4) Uani 1 1 d . . . . .
H103 H 0.3645 1.0935 0.3320 0.023 Uiso 1 1 calc R . . . .
C104 C 0.3887(2) 0.99146(17) 0.39492(8) 0.0174(4) Uani 1 1 d . . . . .
H104 H 0.3001 1.0060 0.4081 0.021 Uiso 1 1 calc R . . . .
C105 C 0.48116(19) 0.91967(16) 0.42095(7) 0.0145(4) Uani 1 1 d . . . . .
C106 C 0.4604(2) 0.86291(16) 0.47009(7) 0.0145(4) Uani 1 1 d . . . . .
C107 C 0.3429(2) 0.86530(17) 0.49962(8) 0.0183(4) Uani 1 1 d . . . . .
H107 H 0.2623 0.9057 0.4882 0.022 Uiso 1 1 calc R . . . .
C108 C 0.3457(2) 0.80744(18) 0.54620(8) 0.0191(4) Uani 1 1 d . . . . .
H108 H 0.2651 0.8073 0.5659 0.023 Uiso 1 1 calc R . . . .
C109 C 0.4640(2) 0.74986(17) 0.56447(7) 0.0165(4) Uani 1 1 d . . . . .
H109 H 0.4640 0.7119 0.5965 0.020 Uiso 1 1 calc R . . . .
C110 C 0.58236(19) 0.74837(17) 0.53547(7) 0.0149(4) Uani 1 1 d . . . . .
C111 C 0.57735(19) 0.80286(16) 0.48847(7) 0.0141(4) Uani 1 1 d . . . . .
C112 C 0.7206(2) 0.69794(17) 0.55161(7) 0.0158(4) Uani 1 1 d . . . . .
H11A H 0.7071 0.6193 0.5646 0.019 Uiso 1 1 calc R . . . .
H11B H 0.7631 0.7445 0.5795 0.019 Uiso 1 1 calc R . . . .
C113 C 0.95807(19) 0.73446(18) 0.52498(8) 0.0180(4) Uani 1 1 d . . . . .
H11C H 1.0273 0.7091 0.5005 0.022 Uiso 1 1 calc R . . . .
H11D H 0.9820 0.6989 0.5584 0.022 Uiso 1 1 calc R . . . .
C114 C 0.9644(2) 0.86382(18) 0.53016(8) 0.0211(4) Uani 1 1 d . . . . .
H11E H 0.9625 0.8988 0.4962 0.032 Uiso 1 1 calc GR . . . .
H11F H 1.0502 0.8856 0.5488 0.032 Uiso 1 1 calc GR . . . .
H11G H 0.8847 0.8907 0.5489 0.032 Uiso 1 1 calc GR . . . .
C115 C 0.8299(2) 0.57377(17) 0.48873(8) 0.0178(4) Uani 1 1 d . . . . .
H11H H 0.8708 0.5268 0.5168 0.021 Uiso 1 1 calc R . . . .
H11I H 0.8949 0.5722 0.4604 0.021 Uiso 1 1 calc R . . . .
C116 C 0.6953(2) 0.51955(18) 0.47060(9) 0.0237(4) Uani 1 1 d . . . . .
H11J H 0.6554 0.5636 0.4419 0.036 Uiso 1 1 calc GR . . . .
H11K H 0.6305 0.5191 0.4985 0.036 Uiso 1 1 calc GR . . . .
H11L H 0.7125 0.4407 0.4597 0.036 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Pd1 Cl1 2.4231(5) . ?
Pd1 N1 2.0639(16) . ?
Pd1 N2 2.1145(16) . ?
Pd1 C11 1.9184(18) . ?
N1 C1 1.343(2) . ?
N1 C5 1.379(2) . ?
N2 C12 1.521(2) . ?
N2 C13 1.503(2) . ?
N2 C15 1.496(2) . ?
C1 H1 0.9500 . ?
C1 C2 1.388(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.384(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.389(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.389(3) . ?
C5 C6 1.466(3) . ?
C6 C7 1.397(3) . ?
C6 C11 1.403(3) . ?
C7 H7 0.9500 . ?
C7 C8 1.397(3) . ?
C8 H8 0.9500 . ?
C8 C9 1.394(3) . ?
C9 H9 0.9500 . ?
C9 C10 1.396(3) . ?
C10 C11 1.387(3) . ?
C10 C12 1.498(3) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C13 C14 1.507(3) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C15 C16 1.512(3) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
Pd11 Cl11 2.4199(5) . ?
Pd11 N101 2.0499(16) . ?
Pd11 N102 2.1077(16) . ?
Pd11 C111 1.9162(19) . ?
N101 C101 1.342(2) . ?
N101 C105 1.370(2) . ?
N102 C112 1.524(2) . ?
N102 C113 1.498(2) . ?
N102 C115 1.499(2) . ?
C101 H101 0.9500 . ?
C101 C102 1.383(3) . ?
C102 H102 0.9500 . ?
C102 C103 1.382(3) . ?
C103 H103 0.9500 . ?
C103 C104 1.391(3) . ?
C104 H104 0.9500 . ?
C104 C105 1.387(3) . ?
C105 C106 1.471(3) . ?
C106 C107 1.398(3) . ?
C106 C111 1.400(3) . ?
C107 H107 0.9500 . ?
C107 C108 1.397(3) . ?
C108 H108 0.9500 . ?
C108 C109 1.396(3) . ?
C109 H109 0.9500 . ?
C109 C110 1.396(3) . ?
C110 C111 1.388(3) . ?
C110 C112 1.505(3) . ?
C112 H11A 0.9900 . ?
C112 H11B 0.9900 . ?
C113 H11C 0.9900 . ?
C113 H11D 0.9900 . ?
C113 C114 1.517(3) . ?
C114 H11E 0.9800 . ?
C114 H11F 0.9800 . ?
C114 H11G 0.9800 . ?
C115 H11H 0.9900 . ?
C115 H11I 0.9900 . ?
C115 C116 1.507(3) . ?
C116 H11J 0.9800 . ?
C116 H11K 0.9800 . ?
C116 H11L 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 Cl1 100.83(4) . . ?
N1 Pd1 N2 161.94(6) . . ?
N2 Pd1 Cl1 96.75(4) . . ?
C11 Pd1 Cl1 177.85(6) . . ?
C11 Pd1 N1 80.00(7) . . ?
C11 Pd1 N2 82.29(7) . . ?
C1 N1 Pd1 126.33(13) . . ?
C1 N1 C5 118.83(16) . . ?
C5 N1 Pd1 114.80(12) . . ?
C12 N2 Pd1 109.23(11) . . ?
C13 N2 Pd1 108.28(12) . . ?
C13 N2 C12 109.64(14) . . ?
C15 N2 Pd1 114.13(11) . . ?
C15 N2 C12 109.21(14) . . ?
C15 N2 C13 106.26(14) . . ?
N1 C1 H1 118.7 . . ?
N1 C1 C2 122.60(17) . . ?
C2 C1 H1 118.7 . . ?
C1 C2 H2 120.6 . . ?
C3 C2 C1 118.85(18) . . ?
C3 C2 H2 120.6 . . ?
C2 C3 H3 120.3 . . ?
C2 C3 C4 119.34(18) . . ?
C4 C3 H3 120.3 . . ?
C3 C4 H4 120.1 . . ?
C5 C4 C3 119.76(18) . . ?
C5 C4 H4 120.1 . . ?
N1 C5 C4 120.58(17) . . ?
N1 C5 C6 112.90(16) . . ?
C4 C5 C6 126.52(17) . . ?
C7 C6 C5 127.65(18) . . ?
C7 C6 C11 118.82(17) . . ?
C11 C6 C5 113.51(16) . . ?
C6 C7 H7 120.6 . . ?
C8 C7 C6 118.83(18) . . ?
C8 C7 H7 120.6 . . ?
C7 C8 H8 119.1 . . ?
C9 C8 C7 121.83(18) . . ?
C9 C8 H8 119.1 . . ?
C8 C9 H9 120.2 . . ?
C8 C9 C10 119.62(18) . . ?
C10 C9 H9 120.2 . . ?
C9 C10 C12 126.00(18) . . ?
C11 C10 C9 118.53(18) . . ?
C11 C10 C12 115.40(17) . . ?
C6 C11 Pd1 118.47(14) . . ?
C10 C11 Pd1 119.14(14) . . ?
C10 C11 C6 122.36(17) . . ?
N2 C12 H12A 109.6 . . ?
N2 C12 H12B 109.6 . . ?
C10 C12 N2 110.43(15) . . ?
C10 C12 H12A 109.6 . . ?
C10 C12 H12B 109.6 . . ?
H12A C12 H12B 108.1 . . ?
N2 C13 H13A 108.7 . . ?
N2 C13 H13B 108.7 . . ?
N2 C13 C14 114.29(15) . . ?
H13A C13 H13B 107.6 . . ?
C14 C13 H13A 108.7 . . ?
C14 C13 H13B 108.7 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
N2 C15 H15A 108.8 . . ?
N2 C15 H15B 108.8 . . ?
N2 C15 C16 113.95(16) . . ?
H15A C15 H15B 107.7 . . ?
C16 C15 H15A 108.8 . . ?
C16 C15 H15B 108.8 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
N101 Pd11 Cl11 99.41(5) . . ?
N101 Pd11 N102 163.21(6) . . ?
N102 Pd11 Cl11 97.38(4) . . ?
C111 Pd11 Cl11 178.69(6) . . ?
C111 Pd11 N101 80.36(7) . . ?
C111 Pd11 N102 82.86(7) . . ?
C101 N101 Pd11 125.17(13) . . ?
C101 N101 C105 119.74(16) . . ?
C105 N101 Pd11 115.01(12) . . ?
C112 N102 Pd11 109.92(11) . . ?
C113 N102 Pd11 111.53(12) . . ?
C113 N102 C112 108.96(15) . . ?
C113 N102 C115 107.96(15) . . ?
C115 N102 Pd11 109.24(12) . . ?
C115 N102 C112 109.17(14) . . ?
N101 C101 H101 119.0 . . ?
N101 C101 C102 121.98(18) . . ?
C102 C101 H101 119.0 . . ?
C101 C102 H102 120.4 . . ?
C103 C102 C101 119.11(18) . . ?
C103 C102 H102 120.4 . . ?
C102 C103 H103 120.4 . . ?
C102 C103 C104 119.13(18) . . ?
C104 C103 H103 120.4 . . ?
C103 C104 H104 120.1 . . ?
C105 C104 C103 119.87(18) . . ?
C105 C104 H104 120.1 . . ?
N101 C105 C104 120.12(17) . . ?
N101 C105 C106 113.06(16) . . ?
C104 C105 C106 126.80(17) . . ?
C107 C106 C105 128.08(18) . . ?
C107 C106 C111 118.67(18) . . ?
C111 C106 C105 113.22(16) . . ?
C106 C107 H107 120.5 . . ?
C108 C107 C106 119.08(18) . . ?
C108 C107 H107 120.5 . . ?
C107 C108 H108 119.2 . . ?
C109 C108 C107 121.56(18) . . ?
C109 C108 H108 119.2 . . ?
C108 C109 H109 120.2 . . ?
C108 C109 C110 119.65(18) . . ?
C110 C109 H109 120.2 . . ?
C109 C110 C112 125.90(17) . . ?
C111 C110 C109 118.45(18) . . ?
C111 C110 C112 115.56(17) . . ?
C106 C111 Pd11 118.26(14) . . ?
C110 C111 Pd11 119.21(14) . . ?
C110 C111 C106 122.53(18) . . ?
N102 C112 H11A 109.5 . . ?
N102 C112 H11B 109.5 . . ?
C110 C112 N102 110.75(15) . . ?
C110 C112 H11A 109.5 . . ?
C110 C112 H11B 109.5 . . ?
H11A C112 H11B 108.1 . . ?
N102 C113 H11C 109.3 . . ?
N102 C113 H11D 109.3 . . ?
N102 C113 C114 111.68(16) . . ?
H11C C113 H11D 107.9 . . ?
C114 C113 H11C 109.3 . . ?
C114 C113 H11D 109.3 . . ?
C113 C114 H11E 109.5 . . ?
C113 C114 H11F 109.5 . . ?
C113 C114 H11G 109.5 . . ?
H11E C114 H11F 109.5 . . ?
H11E C114 H11G 109.5 . . ?
H11F C114 H11G 109.5 . . ?
N102 C115 H11H 108.6 . . ?
N102 C115 H11I 108.6 . . ?
N102 C115 C116 114.66(16) . . ?
H11H C115 H11I 107.6 . . ?
C116 C115 H11H 108.6 . . ?
C116 C115 H11I 108.6 . . ?
C115 C116 H11J 109.5 . . ?
C115 C116 H11K 109.5 . . ?
C115 C116 H11L 109.5 . . ?
H11J C116 H11K 109.5 . . ?
H11J C116 H11L 109.5 . . ?
H11K C116 H11L 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
Pd1 N1 C1 C2 177.03(14) . . . . ?
Pd1 N1 C5 C4 -175.63(14) . . . . ?
Pd1 N1 C5 C6 4.82(19) . . . . ?
Pd1 N2 C12 C10 19.96(18) . . . . ?
Pd1 N2 C13 C14 -56.64(18) . . . . ?
Pd1 N2 C15 C16 50.00(19) . . . . ?
N1 C1 C2 C3 -1.1(3) . . . . ?
N1 C5 C6 C7 177.36(18) . . . . ?
N1 C5 C6 C11 -1.2(2) . . . . ?
C1 N1 C5 C4 2.1(3) . . . . ?
C1 N1 C5 C6 -177.40(16) . . . . ?
C1 C2 C3 C4 1.0(3) . . . . ?
C2 C3 C4 C5 0.6(3) . . . . ?
C3 C4 C5 N1 -2.2(3) . . . . ?
C3 C4 C5 C6 177.25(18) . . . . ?
C4 C5 C6 C7 -2.2(3) . . . . ?
C4 C5 C6 C11 179.25(18) . . . . ?
C5 N1 C1 C2 -0.5(3) . . . . ?
C5 C6 C7 C8 -177.66(19) . . . . ?
C5 C6 C11 Pd1 -3.3(2) . . . . ?
C5 C6 C11 C10 178.59(17) . . . . ?
C6 C7 C8 C9 -1.0(3) . . . . ?
C7 C6 C11 Pd1 177.97(14) . . . . ?
C7 C6 C11 C10 -0.1(3) . . . . ?
C7 C8 C9 C10 0.3(3) . . . . ?
C8 C9 C10 C11 0.4(3) . . . . ?
C8 C9 C10 C12 177.45(18) . . . . ?
C9 C10 C11 Pd1 -178.62(14) . . . . ?
C9 C10 C11 C6 -0.5(3) . . . . ?
C9 C10 C12 N2 166.48(18) . . . . ?
C11 C6 C7 C8 0.9(3) . . . . ?
C11 C10 C12 N2 -16.4(2) . . . . ?
C12 N2 C13 C14 62.4(2) . . . . ?
C12 N2 C15 C16 -72.6(2) . . . . ?
C12 C10 C11 Pd1 4.0(2) . . . . ?
C12 C10 C11 C6 -177.85(17) . . . . ?
C13 N2 C12 C10 -98.55(18) . . . . ?
C13 N2 C15 C16 169.26(16) . . . . ?
C15 N2 C12 C10 145.40(15) . . . . ?
C15 N2 C13 C14 -179.65(16) . . . . ?
Pd11 N101 C101 C102 -175.13(15) . . . . ?
Pd11 N101 C105 C104 176.35(14) . . . . ?
Pd11 N101 C105 C106 -2.5(2) . . . . ?
Pd11 N102 C112 C110 13.74(18) . . . . ?
Pd11 N102 C113 C114 43.95(19) . . . . ?
Pd11 N102 C115 C116 -60.23(18) . . . . ?
N101 C101 C102 C103 -0.6(3) . . . . ?
N101 C105 C106 C107 -178.41(19) . . . . ?
N101 C105 C106 C111 3.5(2) . . . . ?
C101 N101 C105 C104 -0.7(3) . . . . ?
C101 N101 C105 C106 -179.54(17) . . . . ?
C101 C102 C103 C104 -1.2(3) . . . . ?
C102 C103 C104 C105 2.1(3) . . . . ?
C103 C104 C105 N101 -1.1(3) . . . . ?
C103 C104 C105 C106 177.55(19) . . . . ?
C104 C105 C106 C107 2.8(3) . . . . ?
C104 C105 C106 C111 -175.28(19) . . . . ?
C105 N101 C101 C102 1.6(3) . . . . ?
C105 C106 C107 C108 -178.35(19) . . . . ?
C105 C106 C111 Pd11 -3.0(2) . . . . ?
C105 C106 C111 C110 176.46(18) . . . . ?
C106 C107 C108 C109 1.6(3) . . . . ?
C107 C106 C111 Pd11 178.71(15) . . . . ?
C107 C106 C111 C110 -1.8(3) . . . . ?
C107 C108 C109 C110 -0.8(3) . . . . ?
C108 C109 C110 C111 -1.3(3) . . . . ?
C108 C109 C110 C112 175.11(19) . . . . ?
C109 C110 C111 Pd11 -177.90(14) . . . . ?
C109 C110 C111 C106 2.7(3) . . . . ?
C109 C110 C112 N102 170.73(18) . . . . ?
C111 C106 C107 C108 -0.3(3) . . . . ?
C111 C110 C112 N102 -12.8(2) . . . . ?
C112 N102 C113 C114 -77.58(19) . . . . ?
C112 N102 C115 C116 60.0(2) . . . . ?
C112 C110 C111 Pd11 5.3(2) . . . . ?
C112 C110 C111 C106 -174.12(18) . . . . ?
C113 N102 C112 C110 136.25(16) . . . . ?
C113 N102 C115 C116 178.32(17) . . . . ?
C115 N102 C112 C110 -106.07(17) . . . . ?
C115 N102 C113 C114 163.97(16) . . . . ?

####################################################################### 
# 
# 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_4c
_database_code_depnum_ccdc_archive 'CCDC 1038594'
_audit_update_record             
;
2014-12-10 deposited with the CCDC.
2016-06-08 downloaded from the CCDC.
;
_audit_creation_date             2014-02-04
_audit_creation_method           
;
Olex2 1.2
(compiled 2013.12.10 svn.r2850 for OlexSys, GUI svn.r4736)
;
_shelxl_version_number           2014-1
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C16 H17 Cl N2 O Pd'
_chemical_formula_sum            'C16 H17 Cl1 N2 O1 Pd1 '
_chemical_formula_weight         395.18
_chemical_melting_point          ?
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'
Pd Pd -0.9988 1.0072 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   6.9704(5)
_cell_length_b                   17.1706(11)
_cell_length_c                   12.2014(9)
_cell_angle_alpha                90
_cell_angle_beta                 97.943(2)
_cell_angle_gamma                90
_cell_volume                     1446.33(18)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9876
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      2.4
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.467
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.796
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_process_details   
;
CrystalClear-SM Expert 3.1 b27 (Rigaku, 2013)
;
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.815
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       Block
_exptl_crystal_F_000             792
_exptl_crystal_size_max          0.09
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.04
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0246
_diffrn_reflns_av_unetI/netI     0.0210
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            9733
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        27.500
_diffrn_reflns_theta_max         27.484
_diffrn_reflns_theta_min         2.372
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_detector_type            'Rigaku HG Saturn724+ (2x2 bin mode)'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'four-circle κ diffractometer'
_diffrn_measurement_device_type  'Rigaku AFC12 (Right)'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_measurement_specimen_support 'MiTeGen MicroMesh'
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      -0.067800
_diffrn_orient_matrix_UB_12      -0.125950
_diffrn_orient_matrix_UB_13      0.022856
_diffrn_orient_matrix_UB_21      0.032863
_diffrn_orient_matrix_UB_22      -0.009124
_diffrn_orient_matrix_UB_23      0.047207
_diffrn_orient_matrix_UB_31      -0.061090
_diffrn_orient_matrix_UB_32      0.028450
_diffrn_orient_matrix_UB_33      0.048026
_diffrn_radiation_collimation    0.3
_diffrn_radiation_monochromator  'Confocal mirrors, VHF Varimax'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           55.0
_diffrn_source_power             2.475
_diffrn_source_target            Mo
_diffrn_source_type              'Rotating Anode'
_diffrn_source_voltage           45.0
_diffrn_special_details          
;
 ?
;
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3077
_reflns_number_total             3305
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrystalClear-SM Expert 3.1 b27 (Rigaku, 2013)'
_computing_data_collection       'CrystalClear-SM Expert 3.1 b27 (Rigaku, 2013)'
_computing_data_reduction        'CrystalClear-SM Expert 3.1 b27 (Rigaku, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.480
_refine_diff_density_min         -0.628
_refine_diff_density_rms         0.081
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.187
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         3305
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0249
_refine_ls_R_factor_gt           0.0229
_refine_ls_restrained_S_all      1.187
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0143P)²+2.4212P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0556
_refine_ls_wR_factor_ref         0.0562
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C13(H13A,H13B), C14(H14A,H14B), C15(H15A,H15B), C16(H16A,H16B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C7(H7), C8(H8), C9(H9)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Pd1 Pd 0.33877(2) 0.14929(2) 0.44713(2) 0.01029(6) Uani 1 1 d . . . . .
Cl1 Cl 0.40187(9) 0.19532(3) 0.26696(5) 0.01750(12) Uani 1 1 d . . . . .
O1 O 0.3050(3) 0.42408(10) 0.50278(14) 0.0187(4) Uani 1 1 d . . . . .
N1 N 0.2869(3) 0.03457(11) 0.40615(16) 0.0121(4) Uani 1 1 d . . . . .
N2 N 0.3487(3) 0.25669(11) 0.53407(16) 0.0116(4) Uani 1 1 d . . . . .
C1 C 0.2830(3) 0.00368(14) 0.30491(19) 0.0147(4) Uani 1 1 d . . . . .
H1 H 0.3131 0.0359 0.2464 0.018 Uiso 1 1 calc R . . . .
C2 C 0.2366(3) -0.07377(14) 0.2830(2) 0.0167(5) Uani 1 1 d . . . . .
H2 H 0.2334 -0.0941 0.2103 0.020 Uiso 1 1 calc R . . . .
C3 C 0.1952(3) -0.12086(14) 0.3685(2) 0.0169(5) Uani 1 1 d . . . . .
H3 H 0.1619 -0.1740 0.3552 0.020 Uiso 1 1 calc R . . . .
C4 C 0.2026(3) -0.08973(14) 0.4742(2) 0.0153(5) Uani 1 1 d . . . . .
H4 H 0.1773 -0.1217 0.5341 0.018 Uiso 1 1 calc R . . . .
C5 C 0.2473(3) -0.01156(13) 0.49145(19) 0.0123(4) Uani 1 1 d . . . . .
C6 C 0.2555(3) 0.03035(13) 0.59624(19) 0.0121(4) Uani 1 1 d . . . . .
C7 C 0.2304(3) 0.00011(14) 0.6991(2) 0.0146(4) Uani 1 1 d . . . . .
H7 H 0.2045 -0.0538 0.7070 0.017 Uiso 1 1 calc R . . . .
C8 C 0.2437(3) 0.04945(14) 0.79027(19) 0.0155(5) Uani 1 1 d . . . . .
H8 H 0.2257 0.0289 0.8604 0.019 Uiso 1 1 calc R . . . .
C9 C 0.2828(3) 0.12858(14) 0.78023(19) 0.0134(4) Uani 1 1 d . . . . .
H9 H 0.2898 0.1616 0.8432 0.016 Uiso 1 1 calc R . . . .
C10 C 0.3115(3) 0.15932(13) 0.67829(19) 0.0119(4) Uani 1 1 d . . . . .
C11 C 0.2957(3) 0.10956(13) 0.58818(19) 0.0120(4) Uani 1 1 d . . . . .
C12 C 0.3707(3) 0.24125(13) 0.65788(18) 0.0139(4) Uani 1 1 d . . . . .
H12A H 0.5071 0.2495 0.6908 0.017 Uiso 1 1 calc R . . . .
H12B H 0.2886 0.2780 0.6933 0.017 Uiso 1 1 calc R . . . .
C13 C 0.5060(3) 0.30924(14) 0.5067(2) 0.0146(5) Uani 1 1 d . . . . .
H13A H 0.5029 0.3110 0.4254 0.018 Uiso 1 1 calc R . . . .
H13B H 0.6330 0.2877 0.5392 0.018 Uiso 1 1 calc R . . . .
C14 C 0.4863(4) 0.39122(14) 0.5498(2) 0.0173(5) Uani 1 1 d . . . . .
H14A H 0.4945 0.3901 0.6314 0.021 Uiso 1 1 calc R . . . .
H14B H 0.5937 0.4239 0.5303 0.021 Uiso 1 1 calc R . . . .
C15 C 0.1492(4) 0.37916(14) 0.5345(2) 0.0171(5) Uani 1 1 d . . . . .
H15A H 0.0243 0.4025 0.5021 0.021 Uiso 1 1 calc R . . . .
H15B H 0.1556 0.3802 0.6161 0.021 Uiso 1 1 calc R . . . .
C16 C 0.1590(3) 0.29510(13) 0.49547(19) 0.0137(4) Uani 1 1 d . . . . .
H16A H 0.0543 0.2649 0.5227 0.016 Uiso 1 1 calc R . . . .
H16B H 0.1358 0.2941 0.4136 0.016 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 Cl1 2.4327(6) . ?
Pd1 N1 2.0521(19) . ?
Pd1 N2 2.1239(19) . ?
Pd1 C11 1.913(2) . ?
O1 C14 1.430(3) . ?
O1 C15 1.428(3) . ?
N1 C1 1.341(3) . ?
N1 C5 1.366(3) . ?
N2 C12 1.520(3) . ?
N2 C13 1.493(3) . ?
N2 C16 1.495(3) . ?
C1 H1 0.9500 . ?
C1 C2 1.386(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.382(4) . ?
C3 H3 0.9500 . ?
C3 C4 1.391(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.387(3) . ?
C5 C6 1.461(3) . ?
C6 C7 1.391(3) . ?
C6 C11 1.395(3) . ?
C7 H7 0.9500 . ?
C7 C8 1.391(3) . ?
C8 H8 0.9500 . ?
C8 C9 1.395(3) . ?
C9 H9 0.9500 . ?
C9 C10 1.391(3) . ?
C10 C11 1.385(3) . ?
C10 C12 1.496(3) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C13 C14 1.515(3) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C15 C16 1.525(3) . ?
C16 H16A 0.9900 . ?
C16 H16B 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 Cl1 98.02(6) . . ?
N1 Pd1 N2 161.39(8) . . ?
N2 Pd1 Cl1 99.89(5) . . ?
C11 Pd1 Cl1 177.69(7) . . ?
C11 Pd1 N1 80.36(9) . . ?
C11 Pd1 N2 81.88(9) . . ?
C15 O1 C14 109.96(18) . . ?
C1 N1 Pd1 125.76(17) . . ?
C1 N1 C5 119.5(2) . . ?
C5 N1 Pd1 114.73(15) . . ?
C12 N2 Pd1 109.68(13) . . ?
C13 N2 Pd1 112.81(14) . . ?
C13 N2 C12 110.56(17) . . ?
C13 N2 C16 107.94(18) . . ?
C16 N2 Pd1 105.03(13) . . ?
C16 N2 C12 110.68(18) . . ?
N1 C1 H1 118.9 . . ?
N1 C1 C2 122.1(2) . . ?
C2 C1 H1 118.9 . . ?
C1 C2 H2 120.6 . . ?
C3 C2 C1 118.9(2) . . ?
C3 C2 H2 120.6 . . ?
C2 C3 H3 120.3 . . ?
C2 C3 C4 119.4(2) . . ?
C4 C3 H3 120.3 . . ?
C3 C4 H4 120.3 . . ?
C5 C4 C3 119.4(2) . . ?
C5 C4 H4 120.3 . . ?
N1 C5 C4 120.7(2) . . ?
N1 C5 C6 113.2(2) . . ?
C4 C5 C6 126.1(2) . . ?
C7 C6 C5 127.7(2) . . ?
C7 C6 C11 118.6(2) . . ?
C11 C6 C5 113.7(2) . . ?
C6 C7 H7 120.3 . . ?
C6 C7 C8 119.4(2) . . ?
C8 C7 H7 120.3 . . ?
C7 C8 H8 119.5 . . ?
C7 C8 C9 121.0(2) . . ?
C9 C8 H8 119.5 . . ?
C8 C9 H9 119.9 . . ?
C10 C9 C8 120.2(2) . . ?
C10 C9 H9 119.9 . . ?
C9 C10 C12 125.6(2) . . ?
C11 C10 C9 118.1(2) . . ?
C11 C10 C12 116.2(2) . . ?
C6 C11 Pd1 117.98(17) . . ?
C10 C11 Pd1 119.27(17) . . ?
C10 C11 C6 122.7(2) . . ?
N2 C12 H12A 109.7 . . ?
N2 C12 H12B 109.7 . . ?
C10 C12 N2 109.69(18) . . ?
C10 C12 H12A 109.7 . . ?
C10 C12 H12B 109.7 . . ?
H12A C12 H12B 108.2 . . ?
N2 C13 H13A 109.1 . . ?
N2 C13 H13B 109.1 . . ?
N2 C13 C14 112.32(19) . . ?
H13A C13 H13B 107.9 . . ?
C14 C13 H13A 109.1 . . ?
C14 C13 H13B 109.1 . . ?
O1 C14 C13 110.19(19) . . ?
O1 C14 H14A 109.6 . . ?
O1 C14 H14B 109.6 . . ?
C13 C14 H14A 109.6 . . ?
C13 C14 H14B 109.6 . . ?
H14A C14 H14B 108.1 . . ?
O1 C15 H15A 109.4 . . ?
O1 C15 H15B 109.4 . . ?
O1 C15 C16 110.96(19) . . ?
H15A C15 H15B 108.0 . . ?
C16 C15 H15A 109.4 . . ?
C16 C15 H15B 109.4 . . ?
N2 C16 C15 113.28(18) . . ?
N2 C16 H16A 108.9 . . ?
N2 C16 H16B 108.9 . . ?
C15 C16 H16A 108.9 . . ?
C15 C16 H16B 108.9 . . ?
H16A C16 H16B 107.7 . . ?

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
Pd1 N1 C1 C2 -176.49(17) . . . . ?
Pd1 N1 C5 C4 177.64(17) . . . . ?
Pd1 N1 C5 C6 -1.6(2) . . . . ?
Pd1 N2 C12 C10 -19.2(2) . . . . ?
Pd1 N2 C13 C14 168.03(15) . . . . ?
Pd1 N2 C16 C15 -170.89(16) . . . . ?
O1 C15 C16 N2 55.1(3) . . . . ?
N1 C1 C2 C3 -0.7(3) . . . . ?
N1 C5 C6 C7 -177.2(2) . . . . ?
N1 C5 C6 C11 2.0(3) . . . . ?
N2 C13 C14 O1 -59.6(2) . . . . ?
C1 N1 C5 C4 -0.3(3) . . . . ?
C1 N1 C5 C6 -179.51(19) . . . . ?
C1 C2 C3 C4 -0.6(3) . . . . ?
C2 C3 C4 C5 1.4(3) . . . . ?
C3 C4 C5 N1 -1.0(3) . . . . ?
C3 C4 C5 C6 178.1(2) . . . . ?
C4 C5 C6 C7 3.6(4) . . . . ?
C4 C5 C6 C11 -177.2(2) . . . . ?
C5 N1 C1 C2 1.2(3) . . . . ?
C5 C6 C7 C8 180.0(2) . . . . ?
C5 C6 C11 Pd1 -1.4(3) . . . . ?
C5 C6 C11 C10 -179.3(2) . . . . ?
C6 C7 C8 C9 -0.4(3) . . . . ?
C7 C6 C11 Pd1 177.83(16) . . . . ?
C7 C6 C11 C10 -0.1(3) . . . . ?
C7 C8 C9 C10 -0.7(3) . . . . ?
C8 C9 C10 C11 1.4(3) . . . . ?
C8 C9 C10 C12 -174.6(2) . . . . ?
C9 C10 C11 Pd1 -178.91(16) . . . . ?
C9 C10 C11 C6 -1.0(3) . . . . ?
C9 C10 C12 N2 -169.0(2) . . . . ?
C11 C6 C7 C8 0.8(3) . . . . ?
C11 C10 C12 N2 15.0(3) . . . . ?
C12 N2 C13 C14 -68.7(2) . . . . ?
C12 N2 C16 C15 70.8(2) . . . . ?
C12 C10 C11 Pd1 -2.5(3) . . . . ?
C12 C10 C11 C6 175.3(2) . . . . ?
C13 N2 C12 C10 -144.18(19) . . . . ?
C13 N2 C16 C15 -50.3(2) . . . . ?
C14 O1 C15 C16 -59.5(2) . . . . ?
C15 O1 C14 C13 61.8(2) . . . . ?
C16 N2 C12 C10 96.3(2) . . . . ?
C16 N2 C13 C14 52.5(2) . . . . ?

####################################################################### 
# 
# 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_7a
_database_code_depnum_ccdc_archive 'CCDC 1476634'
_audit_update_record             
;
2016-04-26 deposited with the CCDC.
2016-06-08 downloaded from the CCDC.
;

#2014ncs0269za

_audit_creation_date             2016-04-25
_audit_creation_method           
;
Olex2 1.2-alpha
(compiled 2016.02.24 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C24 H19 Cl N O P Pd'
_chemical_formula_sum            'C24 H19 Cl N O P Pd'
_chemical_formula_weight         510.22
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C24 H19 N1 O1 P1 Cl1 Pd1'
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'
P P 0.1023 0.0942 '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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   12.2558(3)
_cell_length_b                   9.9099(3)
_cell_length_c                   17.4367(5)
_cell_angle_alpha                90
_cell_angle_beta                 109.768(3)
_cell_angle_gamma                90
_cell_volume                     1992.95(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    10040
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      29.6730
_cell_measurement_theta_min      2.4400
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.162
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.92345
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.700
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       Shard
_exptl_crystal_F_000             1024
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.04
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0230
_diffrn_reflns_av_unetI/netI     0.0274
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            12267
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.484
_diffrn_reflns_theta_min         2.478
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_detector_type            'Rigaku HG Saturn724+ (2x2 bin mode)'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -107.00  31.00   1.00    5.00    --  -17.00 -24.00 147.00  138
  2  ω    -64.00  22.00   1.00    5.00    --  -17.00 -72.00 -17.00   86
  3  ω    -25.00  -1.00   1.00    5.00    --  -17.00 -72.00 114.00   24
  4  ω   -107.00 -58.00   1.00    5.00    --  -17.00   8.00 -50.00   49
;
_diffrn_measurement_device       'four-circle κ goniometer'
_diffrn_measurement_device_type  
'Rigaku FRE+ equipped with HF Varimax confocal mirrors and an AFC12 goniometer and HG Saturn 724+ detector'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_measurement_specimen_support 'MiTeGen MicroLoop'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0493078000
_diffrn_orient_matrix_UB_12      0.0298091000
_diffrn_orient_matrix_UB_13      0.0291629000
_diffrn_orient_matrix_UB_21      -0.0194358000
_diffrn_orient_matrix_UB_22      0.0647050000
_diffrn_orient_matrix_UB_23      -0.0162919000
_diffrn_orient_matrix_UB_31      -0.0311457000
_diffrn_orient_matrix_UB_32      0.0067096000
_diffrn_orient_matrix_UB_33      0.0274742000
_diffrn_radiation_collimation    0.2
_diffrn_radiation_monochromator  'Confocal mirrors, HF Varimax'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           55.0
_diffrn_source_power             2.475
_diffrn_source_target            Mo
_diffrn_source_type              'Rigaku FRE+'
_diffrn_source_voltage           45.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4046
_reflns_number_total             4548
_reflns_odcompleteness_completeness 99.26
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.42
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrystalClear-SM Expert 3.1 b27 (Rigaku, 2013)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.760
_refine_diff_density_min         -0.456
_refine_diff_density_rms         0.081
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     262
_refine_ls_number_reflns         4548
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0321
_refine_ls_R_factor_gt           0.0268
_refine_ls_restrained_S_all      1.038
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0326P)²+1.4721P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0649
_refine_ls_wR_factor_ref         0.0673
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C9(H9), C10(H10), C11(H11), C12(H12), C14(H14),
 C15(H15), C16(H16), C17(H17), C18(H18), C20(H20), C21(H21), C22(H22), C23(H23),
  C24(H24)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Pd1 Pd 0.18479(2) 0.45676(2) 0.44973(2) 0.01675(6) Uani 1 1 d . . . . .
Cl1 Cl 0.21059(5) 0.22964(6) 0.41506(3) 0.02374(13) Uani 1 1 d . . . . .
P1 P 0.20604(5) 0.53711(6) 0.33720(3) 0.01750(12) Uani 1 1 d . . . . .
O1 O 0.19505(14) 0.69847(16) 0.32761(9) 0.0236(3) Uani 1 1 d . . . . .
N1 N 0.15744(16) 0.4025(2) 0.55837(11) 0.0200(4) Uani 1 1 d . . . . .
C1 C 0.2485(2) 0.7779(2) 0.39962(14) 0.0251(5) Uani 1 1 d . . . . .
H1A H 0.2492 0.8737 0.3837 0.030 Uiso 1 1 calc R . . . .
H1B H 0.3300 0.7486 0.4252 0.030 Uiso 1 1 calc R . . . .
C2 C 0.18744(19) 0.7667(3) 0.46125(13) 0.0229(5) Uani 1 1 d . . . . .
C3 C 0.1598(2) 0.8854(3) 0.49355(15) 0.0279(5) Uani 1 1 d . . . . .
H3 H 0.1714 0.9700 0.4719 0.033 Uiso 1 1 calc R . . . .
C4 C 0.1155(2) 0.8813(3) 0.55707(16) 0.0307(6) Uani 1 1 d . . . . .
H4 H 0.0942 0.9625 0.5773 0.037 Uiso 1 1 calc R . . . .
C5 C 0.1027(2) 0.7591(3) 0.59064(15) 0.0281(5) Uani 1 1 d . . . . .
H5 H 0.0754 0.7564 0.6355 0.034 Uiso 1 1 calc R . . . .
C6 C 0.12981(18) 0.6392(3) 0.55900(13) 0.0210(5) Uani 1 1 d . . . . .
C7 C 0.16654(18) 0.6417(2) 0.49011(13) 0.0200(4) Uani 1 1 d . . . . .
C8 C 0.13027(18) 0.5083(3) 0.59788(14) 0.0208(5) Uani 1 1 d . . . . .
C9 C 0.1130(2) 0.4869(3) 0.67189(15) 0.0268(5) Uani 1 1 d . . . . .
H9 H 0.0936 0.5606 0.6997 0.032 Uiso 1 1 calc R . . . .
C10 C 0.1238(2) 0.3595(3) 0.70478(15) 0.0329(6) Uani 1 1 d . . . . .
H10 H 0.1125 0.3448 0.7554 0.040 Uiso 1 1 calc R . . . .
C11 C 0.1515(2) 0.2528(3) 0.66343(15) 0.0319(6) Uani 1 1 d . . . . .
H11 H 0.1600 0.1640 0.6851 0.038 Uiso 1 1 calc R . . . .
C12 C 0.1666(2) 0.2789(3) 0.59009(14) 0.0256(5) Uani 1 1 d . . . . .
H12 H 0.1841 0.2059 0.5609 0.031 Uiso 1 1 calc R . . . .
C13 C 0.34655(19) 0.4971(2) 0.32976(13) 0.0192(4) Uani 1 1 d . . . . .
C14 C 0.3689(2) 0.5228(2) 0.25788(14) 0.0227(5) Uani 1 1 d . . . . .
H14 H 0.3095 0.5591 0.2122 0.027 Uiso 1 1 calc R . . . .
C15 C 0.4772(2) 0.4957(3) 0.25261(15) 0.0266(5) Uani 1 1 d . . . . .
H15 H 0.4917 0.5122 0.2033 0.032 Uiso 1 1 calc R . . . .
C16 C 0.5638(2) 0.4446(3) 0.31964(16) 0.0271(5) Uani 1 1 d . . . . .
H16 H 0.6383 0.4267 0.3164 0.033 Uiso 1 1 calc R . . . .
C17 C 0.5428(2) 0.4195(3) 0.39100(15) 0.0258(5) Uani 1 1 d . . . . .
H17 H 0.6030 0.3848 0.4368 0.031 Uiso 1 1 calc R . . . .
C18 C 0.4344(2) 0.4445(2) 0.39647(14) 0.0225(5) Uani 1 1 d . . . . .
H18 H 0.4201 0.4258 0.4457 0.027 Uiso 1 1 calc R . . . .
C19 C 0.10288(19) 0.4911(2) 0.23865(13) 0.0196(4) Uani 1 1 d . . . . .
C20 C 0.0671(2) 0.5876(3) 0.17677(14) 0.0263(5) Uani 1 1 d . . . . .
H20 H 0.0963 0.6772 0.1861 0.032 Uiso 1 1 calc R . . . .
C21 C -0.0116(2) 0.5509(3) 0.10143(15) 0.0318(6) Uani 1 1 d . . . . .
H21 H -0.0362 0.6162 0.0592 0.038 Uiso 1 1 calc R . . . .
C22 C -0.0542(2) 0.4225(3) 0.08713(14) 0.0292(6) Uani 1 1 d . . . . .
H22 H -0.1087 0.3994 0.0355 0.035 Uiso 1 1 calc R . . . .
C23 C -0.0180(2) 0.3258(3) 0.14784(14) 0.0260(5) Uani 1 1 d . . . . .
H23 H -0.0468 0.2362 0.1377 0.031 Uiso 1 1 calc R . . . .
C24 C 0.06083(19) 0.3604(3) 0.22397(13) 0.0229(5) Uani 1 1 d . . . . .
H24 H 0.0857 0.2943 0.2658 0.027 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 Cl1 2.3792(6) . ?
Pd1 P1 2.2130(6) . ?
Pd1 N1 2.1022(18) . ?
Pd1 C7 2.003(2) . ?
P1 O1 1.6087(17) . ?
P1 C13 1.814(2) . ?
P1 C19 1.814(2) . ?
O1 C1 1.439(3) . ?
N1 C8 1.356(3) . ?
N1 C12 1.333(3) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C1 C2 1.507(3) . ?
C2 C3 1.395(3) . ?
C2 C7 1.392(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.389(4) . ?
C4 H4 0.9500 . ?
C4 C5 1.377(4) . ?
C5 H5 0.9500 . ?
C5 C6 1.397(3) . ?
C6 C7 1.418(3) . ?
C6 C8 1.463(3) . ?
C8 C9 1.393(3) . ?
C9 H9 0.9500 . ?
C9 C10 1.374(4) . ?
C10 H10 0.9500 . ?
C10 C11 1.385(4) . ?
C11 H11 0.9500 . ?
C11 C12 1.377(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.394(3) . ?
C13 C18 1.391(3) . ?
C14 H14 0.9500 . ?
C14 C15 1.388(3) . ?
C15 H15 0.9500 . ?
C15 C16 1.382(4) . ?
C16 H16 0.9500 . ?
C16 C17 1.376(4) . ?
C17 H17 0.9500 . ?
C17 C18 1.387(3) . ?
C18 H18 0.9500 . ?
C19 C20 1.397(3) . ?
C19 C24 1.386(3) . ?
C20 H20 0.9500 . ?
C20 C21 1.390(3) . ?
C21 H21 0.9500 . ?
C21 C22 1.367(4) . ?
C22 H22 0.9500 . ?
C22 C23 1.384(4) . ?
C23 H23 0.9500 . ?
C23 C24 1.395(3) . ?
C24 H24 0.9500 . ?

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
P1 Pd1 Cl1 92.84(2) . . ?
N1 Pd1 Cl1 93.58(6) . . ?
N1 Pd1 P1 173.41(6) . . ?
C7 Pd1 Cl1 174.42(6) . . ?
C7 Pd1 P1 92.47(7) . . ?
C7 Pd1 N1 81.17(8) . . ?
O1 P1 Pd1 114.77(6) . . ?
O1 P1 C13 104.96(10) . . ?
O1 P1 C19 98.30(10) . . ?
C13 P1 Pd1 112.58(7) . . ?
C19 P1 Pd1 119.75(8) . . ?
C19 P1 C13 104.58(10) . . ?
C1 O1 P1 117.13(14) . . ?
C8 N1 Pd1 113.68(16) . . ?
C12 N1 Pd1 126.32(16) . . ?
C12 N1 C8 120.0(2) . . ?
O1 C1 H1A 109.0 . . ?
O1 C1 H1B 109.0 . . ?
O1 C1 C2 113.12(19) . . ?
H1A C1 H1B 107.8 . . ?
C2 C1 H1A 109.0 . . ?
C2 C1 H1B 109.0 . . ?
C3 C2 C1 118.2(2) . . ?
C7 C2 C1 121.3(2) . . ?
C7 C2 C3 120.3(2) . . ?
C2 C3 H3 119.6 . . ?
C4 C3 C2 120.7(2) . . ?
C4 C3 H3 119.6 . . ?
C3 C4 H4 120.1 . . ?
C5 C4 C3 119.7(2) . . ?
C5 C4 H4 120.1 . . ?
C4 C5 H5 119.9 . . ?
C4 C5 C6 120.3(2) . . ?
C6 C5 H5 119.9 . . ?
C5 C6 C7 120.4(2) . . ?
C5 C6 C8 122.4(2) . . ?
C7 C6 C8 117.1(2) . . ?
C2 C7 Pd1 129.08(17) . . ?
C2 C7 C6 118.1(2) . . ?
C6 C7 Pd1 112.75(17) . . ?
N1 C8 C6 114.4(2) . . ?
N1 C8 C9 119.6(2) . . ?
C9 C8 C6 125.9(2) . . ?
C8 C9 H9 119.9 . . ?
C10 C9 C8 120.2(2) . . ?
C10 C9 H9 119.9 . . ?
C9 C10 H10 120.3 . . ?
C9 C10 C11 119.4(2) . . ?
C11 C10 H10 120.3 . . ?
C10 C11 H11 120.9 . . ?
C12 C11 C10 118.3(2) . . ?
C12 C11 H11 120.9 . . ?
N1 C12 C11 122.6(2) . . ?
N1 C12 H12 118.7 . . ?
C11 C12 H12 118.7 . . ?
C14 C13 P1 120.27(17) . . ?
C18 C13 P1 120.45(17) . . ?
C18 C13 C14 119.2(2) . . ?
C13 C14 H14 119.8 . . ?
C15 C14 C13 120.5(2) . . ?
C15 C14 H14 119.8 . . ?
C14 C15 H15 120.2 . . ?
C16 C15 C14 119.6(2) . . ?
C16 C15 H15 120.2 . . ?
C15 C16 H16 119.8 . . ?
C17 C16 C15 120.4(2) . . ?
C17 C16 H16 119.8 . . ?
C16 C17 H17 119.8 . . ?
C16 C17 C18 120.4(2) . . ?
C18 C17 H17 119.8 . . ?
C13 C18 H18 120.1 . . ?
C17 C18 C13 119.9(2) . . ?
C17 C18 H18 120.1 . . ?
C20 C19 P1 119.71(19) . . ?
C24 C19 P1 120.44(17) . . ?
C24 C19 C20 119.8(2) . . ?
C19 C20 H20 120.4 . . ?
C21 C20 C19 119.1(2) . . ?
C21 C20 H20 120.4 . . ?
C20 C21 H21 119.4 . . ?
C22 C21 C20 121.1(2) . . ?
C22 C21 H21 119.4 . . ?
C21 C22 H22 120.0 . . ?
C21 C22 C23 120.1(2) . . ?
C23 C22 H22 120.0 . . ?
C22 C23 H23 120.1 . . ?
C22 C23 C24 119.8(2) . . ?
C24 C23 H23 120.1 . . ?
C19 C24 C23 120.0(2) . . ?
C19 C24 H24 120.0 . . ?
C23 C24 H24 120.0 . . ?

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
Pd1 P1 O1 C1 40.69(17) . . . . ?
Pd1 P1 C13 C14 170.84(17) . . . . ?
Pd1 P1 C13 C18 -11.2(2) . . . . ?
Pd1 P1 C19 C20 140.90(16) . . . . ?
Pd1 P1 C19 C24 -40.2(2) . . . . ?
Pd1 N1 C8 C6 -2.3(2) . . . . ?
Pd1 N1 C8 C9 -178.29(16) . . . . ?
Pd1 N1 C12 C11 177.38(18) . . . . ?
P1 O1 C1 C2 -69.8(2) . . . . ?
P1 C13 C14 C15 178.25(19) . . . . ?
P1 C13 C18 C17 -177.38(19) . . . . ?
P1 C19 C20 C21 179.75(19) . . . . ?
P1 C19 C24 C23 -179.65(17) . . . . ?
O1 P1 C13 C14 -63.7(2) . . . . ?
O1 P1 C13 C18 114.3(2) . . . . ?
O1 P1 C19 C20 16.1(2) . . . . ?
O1 P1 C19 C24 -165.01(18) . . . . ?
O1 C1 C2 C3 -130.6(2) . . . . ?
O1 C1 C2 C7 54.1(3) . . . . ?
N1 C8 C9 C10 0.3(3) . . . . ?
C1 C2 C3 C4 -172.7(2) . . . . ?
C1 C2 C7 Pd1 -10.4(3) . . . . ?
C1 C2 C7 C6 167.8(2) . . . . ?
C2 C3 C4 C5 2.4(4) . . . . ?
C3 C2 C7 Pd1 174.47(17) . . . . ?
C3 C2 C7 C6 -7.3(3) . . . . ?
C3 C4 C5 C6 -2.5(4) . . . . ?
C4 C5 C6 C7 -2.4(3) . . . . ?
C4 C5 C6 C8 173.0(2) . . . . ?
C5 C6 C7 Pd1 -174.26(17) . . . . ?
C5 C6 C7 C2 7.3(3) . . . . ?
C5 C6 C8 N1 179.4(2) . . . . ?
C5 C6 C8 C9 -4.9(4) . . . . ?
C6 C8 C9 C10 -175.3(2) . . . . ?
C7 C2 C3 C4 2.6(4) . . . . ?
C7 C6 C8 N1 -5.1(3) . . . . ?
C7 C6 C8 C9 170.6(2) . . . . ?
C8 N1 C12 C11 -1.3(4) . . . . ?
C8 C6 C7 Pd1 10.1(2) . . . . ?
C8 C6 C7 C2 -168.3(2) . . . . ?
C8 C9 C10 C11 -0.3(4) . . . . ?
C9 C10 C11 C12 -0.4(4) . . . . ?
C10 C11 C12 N1 1.2(4) . . . . ?
C12 N1 C8 C6 176.5(2) . . . . ?
C12 N1 C8 C9 0.5(3) . . . . ?
C13 P1 O1 C1 -83.43(17) . . . . ?
C13 P1 C19 C20 -91.8(2) . . . . ?
C13 P1 C19 C24 87.1(2) . . . . ?
C13 C14 C15 C16 -0.9(4) . . . . ?
C14 C13 C18 C17 0.5(4) . . . . ?
C14 C15 C16 C17 0.6(4) . . . . ?
C15 C16 C17 C18 0.3(4) . . . . ?
C16 C17 C18 C13 -0.9(4) . . . . ?
C18 C13 C14 C15 0.3(4) . . . . ?
C19 P1 O1 C1 168.98(16) . . . . ?
C19 P1 C13 C14 39.3(2) . . . . ?
C19 P1 C13 C18 -142.8(2) . . . . ?
C19 C20 C21 C22 -0.1(4) . . . . ?
C20 C19 C24 C23 -0.7(3) . . . . ?
C20 C21 C22 C23 -0.8(4) . . . . ?
C21 C22 C23 C24 0.9(4) . . . . ?
C22 C23 C24 C19 -0.1(3) . . . . ?
C24 C19 C20 C21 0.8(4) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_date_sample_completion    2014-05-21
_olex2_date_sample_data_collection 2014-05-21
_olex2_date_sample_submission    2014-04-07
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a MITIGEN holder in oil'
_olex2_submission_original_sample_id 'GR 75b'
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 7.056
_oxdiff_exptl_absorpt_empirical_full_min 0.519
####################################################################### 
# 
# 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_7b
_database_code_depnum_ccdc_archive 'CCDC 1476635'
_audit_update_record             
;
2016-04-26 deposited with the CCDC.
2016-06-08 downloaded from the CCDC.
;

#2014ncs0361za

_audit_creation_date             2016-04-25
_audit_creation_method           
;
Olex2 1.2-alpha
(compiled 2016.02.24 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H17 Cl N O P Pd'
_chemical_formula_sum            'C23 H17 Cl N O P Pd'
_chemical_formula_weight         496.20
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C23 H17 N1 O1 P1 Cl1 Pd1'
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'
P P 0.1023 0.0942 '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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.0641(2)
_cell_length_b                   9.6782(3)
_cell_length_c                   12.7031(4)
_cell_angle_alpha                91.535(3)
_cell_angle_beta                 108.207(3)
_cell_angle_gamma                112.231(3)
_cell_volume                     966.48(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9668
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      29.5560
_cell_measurement_theta_min      2.3700
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.195
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.92532
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.705
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             496
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.07
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0144
_diffrn_reflns_av_unetI/netI     0.0132
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            11298
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.485
_diffrn_reflns_theta_min         2.559
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_detector_type            'Rigaku HG Saturn724+ (2x2 bin mode)'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -107.00  73.00   1.00    5.00    --  -17.00   8.00 -17.00  180
  2  ω    -77.00  22.00   1.00    5.00    --  -17.00 -72.00  81.00   99
  3  ω    -84.00  22.00   1.00    5.00    --  -17.00 -72.00-115.00  106
  4  ω    -27.00  71.00   1.00    5.00    --  -17.00  72.00 -17.00   98
  5  ω    -72.00 -57.00   1.00    5.00    --  -17.00 -40.00-180.00   15
  6  ω    -67.00  -7.00   1.00    5.00    --  -17.00   8.00  16.00   60
;
_diffrn_measurement_device       'four-circle κ goniometer'
_diffrn_measurement_device_type  
'Rigaku FRE+ equipped with HF Varimax confocal mirrors and an AFC12 goniometer and HG Saturn 724+ detector'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_measurement_specimen_support 'MiTeGen MicroLoop'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0018243000
_diffrn_orient_matrix_UB_12      0.0091225000
_diffrn_orient_matrix_UB_13      0.0551051000
_diffrn_orient_matrix_UB_21      -0.0031598000
_diffrn_orient_matrix_UB_22      0.0714621000
_diffrn_orient_matrix_UB_23      -0.0067335000
_diffrn_orient_matrix_UB_31      -0.0901220000
_diffrn_orient_matrix_UB_32      -0.0354068000
_diffrn_orient_matrix_UB_33      -0.0216718000
_diffrn_radiation_collimation    0.2
_diffrn_radiation_monochromator  'Confocal mirrors, HF Varimax'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           55.0
_diffrn_source_power             2.475
_diffrn_source_target            Mo
_diffrn_source_type              'Rigaku FRE+'
_diffrn_source_voltage           45.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4218
_reflns_number_total             4420
_reflns_odcompleteness_completeness 99.68
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.42
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrystalClear-SM Expert 3.1 b27 (Rigaku, 2013)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.489
_refine_diff_density_min         -0.405
_refine_diff_density_rms         0.069
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         4420
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0216
_refine_ls_R_factor_gt           0.0201
_refine_ls_restrained_S_all      1.029
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0266P)²+0.9105P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0508
_refine_ls_wR_factor_ref         0.0514
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C8(H8), C9(H9), C10(H10), C11(H11), C13(H13),
 C14(H14), C15(H15), C16(H16), C17(H17), C19(H19), C20(H20), C21(H21), C22(H22),
  C23(H23)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Pd1 Pd 0.51263(2) 0.69810(2) 0.82866(2) 0.01390(5) Uani 1 1 d . . . . .
Cl1 Cl 0.64802(6) 0.96597(5) 0.88577(4) 0.02082(9) Uani 1 1 d . . . . .
P1 P 0.28744(5) 0.67404(5) 0.68568(3) 0.01416(9) Uani 1 1 d . . . . .
O1 O 0.17569(16) 0.49005(13) 0.64122(10) 0.0184(2) Uani 1 1 d . . . . .
N1 N 0.69213(19) 0.63986(17) 0.94893(12) 0.0178(3) Uani 1 1 d . . . . .
C1 C 0.2564(2) 0.40345(19) 0.69855(14) 0.0172(3) Uani 1 1 d . . . . .
C2 C 0.1844(2) 0.2477(2) 0.66900(15) 0.0210(4) Uani 1 1 d . . . . .
H2 H 0.0799 0.1974 0.6084 0.025 Uiso 1 1 calc R . . . .
C3 C 0.2698(3) 0.1672(2) 0.73064(16) 0.0224(4) Uani 1 1 d . . . . .
H3 H 0.2219 0.0600 0.7116 0.027 Uiso 1 1 calc R . . . .
C4 C 0.4229(2) 0.2385(2) 0.81921(15) 0.0209(4) Uani 1 1 d . . . . .
H4 H 0.4783 0.1809 0.8608 0.025 Uiso 1 1 calc R . . . .
C5 C 0.4946(2) 0.3965(2) 0.84641(14) 0.0181(3) Uani 1 1 d . . . . .
C6 C 0.4095(2) 0.47831(19) 0.78529(14) 0.0163(3) Uani 1 1 d . . . . .
C7 C 0.6553(2) 0.4891(2) 0.93703(15) 0.0181(3) Uani 1 1 d . . . . .
C8 C 0.7643(2) 0.4343(2) 1.00688(16) 0.0229(4) Uani 1 1 d . . . . .
H8 H 0.7388 0.3291 0.9975 0.027 Uiso 1 1 calc R . . . .
C9 C 0.9105(3) 0.5339(2) 1.09018(16) 0.0254(4) Uani 1 1 d . . . . .
H9 H 0.9862 0.4977 1.1387 0.030 Uiso 1 1 calc R . . . .
C10 C 0.9460(2) 0.6867(2) 1.10249(16) 0.0250(4) Uani 1 1 d . . . . .
H10 H 1.0454 0.7569 1.1596 0.030 Uiso 1 1 calc R . . . .
C11 C 0.8329(2) 0.7349(2) 1.02933(15) 0.0212(4) Uani 1 1 d . . . . .
H11 H 0.8569 0.8399 1.0370 0.025 Uiso 1 1 calc R . . . .
C12 C 0.3136(2) 0.73568(19) 0.55751(14) 0.0168(3) Uani 1 1 d . . . . .
C13 C 0.3768(2) 0.6599(2) 0.49981(16) 0.0228(4) Uani 1 1 d . . . . .
H13 H 0.4051 0.5804 0.5291 0.027 Uiso 1 1 calc R . . . .
C14 C 0.3981(3) 0.7004(2) 0.40010(16) 0.0261(4) Uani 1 1 d . . . . .
H14 H 0.4402 0.6481 0.3608 0.031 Uiso 1 1 calc R . . . .
C15 C 0.3580(2) 0.8173(2) 0.35772(15) 0.0245(4) Uani 1 1 d . . . . .
H15 H 0.3722 0.8449 0.2892 0.029 Uiso 1 1 calc R . . . .
C16 C 0.2975(2) 0.8935(2) 0.41517(16) 0.0245(4) Uani 1 1 d . . . . .
H16 H 0.2704 0.9737 0.3860 0.029 Uiso 1 1 calc R . . . .
C17 C 0.2758(2) 0.8538(2) 0.51526(15) 0.0205(3) Uani 1 1 d . . . . .
H17 H 0.2353 0.9074 0.5548 0.025 Uiso 1 1 calc R . . . .
C18 C 0.1352(2) 0.73504(18) 0.71010(14) 0.0160(3) Uani 1 1 d . . . . .
C19 C -0.0225(2) 0.6970(2) 0.62662(15) 0.0221(4) Uani 1 1 d . . . . .
H19 H -0.0482 0.6423 0.5554 0.026 Uiso 1 1 calc R . . . .
C20 C -0.1419(2) 0.7391(2) 0.64773(17) 0.0266(4) Uani 1 1 d . . . . .
H20 H -0.2484 0.7157 0.5902 0.032 Uiso 1 1 calc R . . . .
C21 C -0.1061(2) 0.8154(2) 0.75289(17) 0.0244(4) Uani 1 1 d . . . . .
H21 H -0.1889 0.8426 0.7676 0.029 Uiso 1 1 calc R . . . .
C22 C 0.0498(2) 0.85179(19) 0.83593(15) 0.0200(3) Uani 1 1 d . . . . .
H22 H 0.0733 0.9028 0.9080 0.024 Uiso 1 1 calc R . . . .
C23 C 0.1725(2) 0.81418(18) 0.81470(14) 0.0173(3) Uani 1 1 d . . . . .
H23 H 0.2810 0.8423 0.8712 0.021 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 Cl1 2.3851(4) . ?
Pd1 P1 2.1955(5) . ?
Pd1 N1 2.1180(15) . ?
Pd1 C6 1.9528(17) . ?
P1 O1 1.6551(13) . ?
P1 C12 1.8026(17) . ?
P1 C18 1.7954(17) . ?
O1 C1 1.390(2) . ?
N1 C7 1.361(2) . ?
N1 C11 1.328(2) . ?
C1 C2 1.382(2) . ?
C1 C6 1.381(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.389(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.388(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.400(2) . ?
C5 C6 1.394(2) . ?
C5 C7 1.469(3) . ?
C7 C8 1.386(3) . ?
C8 H8 0.9500 . ?
C8 C9 1.381(3) . ?
C9 H9 0.9500 . ?
C9 C10 1.382(3) . ?
C10 H10 0.9500 . ?
C10 C11 1.387(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.398(2) . ?
C12 C17 1.388(2) . ?
C13 H13 0.9500 . ?
C13 C14 1.385(3) . ?
C14 H14 0.9500 . ?
C14 C15 1.387(3) . ?
C15 H15 0.9500 . ?
C15 C16 1.380(3) . ?
C16 H16 0.9500 . ?
C16 C17 1.388(2) . ?
C17 H17 0.9500 . ?
C18 C19 1.392(3) . ?
C18 C23 1.391(2) . ?
C19 H19 0.9500 . ?
C19 C20 1.384(3) . ?
C20 H20 0.9500 . ?
C20 C21 1.390(3) . ?
C21 H21 0.9500 . ?
C21 C22 1.380(3) . ?
C22 H22 0.9500 . ?
C22 C23 1.390(2) . ?
C23 H23 0.9500 . ?

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
P1 Pd1 Cl1 101.305(16) . . ?
N1 Pd1 Cl1 98.42(4) . . ?
N1 Pd1 P1 160.26(4) . . ?
C6 Pd1 Cl1 177.89(5) . . ?
C6 Pd1 P1 80.74(5) . . ?
C6 Pd1 N1 79.52(7) . . ?
O1 P1 Pd1 106.28(5) . . ?
O1 P1 C12 100.36(7) . . ?
O1 P1 C18 102.71(7) . . ?
C12 P1 Pd1 119.21(6) . . ?
C18 P1 Pd1 118.74(6) . . ?
C18 P1 C12 106.61(8) . . ?
C1 O1 P1 112.85(11) . . ?
C7 N1 Pd1 113.92(12) . . ?
C11 N1 Pd1 126.47(12) . . ?
C11 N1 C7 119.59(16) . . ?
C2 C1 O1 120.59(16) . . ?
C6 C1 O1 117.74(15) . . ?
C6 C1 C2 121.66(17) . . ?
C1 C2 H2 121.0 . . ?
C1 C2 C3 117.92(17) . . ?
C3 C2 H2 121.0 . . ?
C2 C3 H3 119.0 . . ?
C4 C3 C2 122.00(17) . . ?
C4 C3 H3 119.0 . . ?
C3 C4 H4 120.5 . . ?
C3 C4 C5 119.01(17) . . ?
C5 C4 H4 120.5 . . ?
C4 C5 C7 125.86(16) . . ?
C6 C5 C4 119.40(17) . . ?
C6 C5 C7 114.74(15) . . ?
C1 C6 Pd1 122.23(13) . . ?
C1 C6 C5 120.00(16) . . ?
C5 C6 Pd1 117.76(13) . . ?
N1 C7 C5 114.01(15) . . ?
N1 C7 C8 120.61(18) . . ?
C8 C7 C5 125.38(17) . . ?
C7 C8 H8 120.3 . . ?
C9 C8 C7 119.42(18) . . ?
C9 C8 H8 120.3 . . ?
C8 C9 H9 120.2 . . ?
C8 C9 C10 119.58(18) . . ?
C10 C9 H9 120.2 . . ?
C9 C10 H10 120.8 . . ?
C9 C10 C11 118.35(19) . . ?
C11 C10 H10 120.8 . . ?
N1 C11 C10 122.44(18) . . ?
N1 C11 H11 118.8 . . ?
C10 C11 H11 118.8 . . ?
C13 C12 P1 117.25(13) . . ?
C17 C12 P1 123.31(13) . . ?
C17 C12 C13 119.44(16) . . ?
C12 C13 H13 119.9 . . ?
C14 C13 C12 120.26(17) . . ?
C14 C13 H13 119.9 . . ?
C13 C14 H14 120.0 . . ?
C13 C14 C15 119.91(18) . . ?
C15 C14 H14 120.0 . . ?
C14 C15 H15 120.0 . . ?
C16 C15 C14 119.98(17) . . ?
C16 C15 H15 120.0 . . ?
C15 C16 H16 119.8 . . ?
C15 C16 C17 120.47(18) . . ?
C17 C16 H16 119.8 . . ?
C12 C17 C16 119.92(17) . . ?
C12 C17 H17 120.0 . . ?
C16 C17 H17 120.0 . . ?
C19 C18 P1 120.13(13) . . ?
C23 C18 P1 119.63(13) . . ?
C23 C18 C19 120.16(16) . . ?
C18 C19 H19 120.1 . . ?
C20 C19 C18 119.78(17) . . ?
C20 C19 H19 120.1 . . ?
C19 C20 H20 119.9 . . ?
C19 C20 C21 120.12(18) . . ?
C21 C20 H20 119.9 . . ?
C20 C21 H21 120.0 . . ?
C22 C21 C20 120.00(17) . . ?
C22 C21 H21 120.0 . . ?
C21 C22 H22 119.8 . . ?
C21 C22 C23 120.40(16) . . ?
C23 C22 H22 119.8 . . ?
C18 C23 H23 120.3 . . ?
C22 C23 C18 119.49(17) . . ?
C22 C23 H23 120.3 . . ?

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
Pd1 P1 O1 C1 -4.13(11) . . . . ?
Pd1 P1 C12 C13 63.81(15) . . . . ?
Pd1 P1 C12 C17 -115.55(14) . . . . ?
Pd1 P1 C18 C19 -168.36(12) . . . . ?
Pd1 P1 C18 C23 8.53(15) . . . . ?
Pd1 N1 C7 C5 -2.58(17) . . . . ?
Pd1 N1 C7 C8 177.55(12) . . . . ?
Pd1 N1 C11 C10 -178.00(13) . . . . ?
P1 O1 C1 C2 -177.22(13) . . . . ?
P1 O1 C1 C6 2.88(19) . . . . ?
P1 C12 C13 C14 179.26(15) . . . . ?
P1 C12 C17 C16 -179.24(14) . . . . ?
P1 C18 C19 C20 177.34(15) . . . . ?
P1 C18 C23 C22 -175.43(13) . . . . ?
O1 P1 C12 C13 -51.57(15) . . . . ?
O1 P1 C12 C17 129.07(15) . . . . ?
O1 P1 C18 C19 -51.52(15) . . . . ?
O1 P1 C18 C23 125.36(13) . . . . ?
O1 C1 C2 C3 -178.93(15) . . . . ?
O1 C1 C6 Pd1 0.2(2) . . . . ?
O1 C1 C6 C5 179.17(14) . . . . ?
N1 C7 C8 C9 0.9(3) . . . . ?
C1 C2 C3 C4 -0.2(3) . . . . ?
C2 C1 C6 Pd1 -179.71(13) . . . . ?
C2 C1 C6 C5 -0.7(3) . . . . ?
C2 C3 C4 C5 -0.8(3) . . . . ?
C3 C4 C5 C6 1.0(2) . . . . ?
C3 C4 C5 C7 -179.86(16) . . . . ?
C4 C5 C6 Pd1 178.75(12) . . . . ?
C4 C5 C6 C1 -0.3(2) . . . . ?
C4 C5 C7 N1 -177.10(15) . . . . ?
C4 C5 C7 C8 2.8(3) . . . . ?
C5 C7 C8 C9 -178.98(16) . . . . ?
C6 C1 C2 C3 1.0(3) . . . . ?
C6 C5 C7 N1 2.1(2) . . . . ?
C6 C5 C7 C8 -178.06(16) . . . . ?
C7 N1 C11 C10 0.3(3) . . . . ?
C7 C5 C6 Pd1 -0.48(19) . . . . ?
C7 C5 C6 C1 -179.50(14) . . . . ?
C7 C8 C9 C10 -0.1(3) . . . . ?
C8 C9 C10 C11 -0.5(3) . . . . ?
C9 C10 C11 N1 0.4(3) . . . . ?
C11 N1 C7 C5 178.91(14) . . . . ?
C11 N1 C7 C8 -1.0(2) . . . . ?
C12 P1 O1 C1 120.63(12) . . . . ?
C12 P1 C18 C19 53.52(16) . . . . ?
C12 P1 C18 C23 -129.59(13) . . . . ?
C12 C13 C14 C15 0.5(3) . . . . ?
C13 C12 C17 C16 1.4(3) . . . . ?
C13 C14 C15 C16 0.2(3) . . . . ?
C14 C15 C16 C17 -0.2(3) . . . . ?
C15 C16 C17 C12 -0.7(3) . . . . ?
C17 C12 C13 C14 -1.3(3) . . . . ?
C18 P1 O1 C1 -129.54(11) . . . . ?
C18 P1 C12 C13 -158.31(14) . . . . ?
C18 P1 C12 C17 22.33(17) . . . . ?
C18 C19 C20 C21 -1.8(3) . . . . ?
C19 C18 C23 C22 1.5(2) . . . . ?
C19 C20 C21 C22 1.1(3) . . . . ?
C20 C21 C22 C23 0.8(3) . . . . ?
C21 C22 C23 C18 -2.1(3) . . . . ?
C23 C18 C19 C20 0.5(3) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_date_sample_completion    2014-06-02
_olex2_date_sample_data_collection 2014-06-02
_olex2_date_sample_submission    2014-05-16
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a MITIGEN holder in oil'
_olex2_submission_original_sample_id 'GR 83b'
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.160
_oxdiff_exptl_absorpt_empirical_full_min 0.484
