# Electronic Supplementary Material (ESI) for Catalysis Science & Technology.
# This journal is © The Royal Society of Chemistry 2015

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

data_1
_database_code_depnum_ccdc_archive 'CCDC 1054276'
_audit_update_record             
;
2015-03-16 deposited with the CCDC.
2015-05-19 downloaded from the CCDC.
;
#============================================================================= 

_audit_creation_method           
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H16 Cl2 N O P Pd'
_chemical_formula_sum            'C19 H16 Cl2 N O P Pd'
_chemical_formula_weight         482.60

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Pd Pd 0.1215 3.9337 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

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

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

_cell_length_a                   9.3940(5)
_cell_length_b                   10.5702(6)
_cell_length_c                   19.7348(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1959.60(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    293
_cell_measurement_reflns_used    3146
_cell_measurement_theta_min      4.4690
_cell_measurement_theta_max      68.7110

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.636
_exptl_crystal_F_000             960
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.08
_exptl_absorpt_coefficient_mu    10.973
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.37163
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Xcalibur, Onyx, Nova'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 8.2640
_diffrn_reflns_number            6700
_diffrn_reflns_av_unetI/netI     0.0661
_diffrn_reflns_av_R_equivalents  0.0585
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         4.481
_diffrn_reflns_theta_max         69.317
_diffrn_reflns_theta_full        68.310
_diffrn_measured_fraction_theta_max 0.946
_diffrn_measured_fraction_theta_full 0.955
_diffrn_reflns_Laue_measured_fraction_max 0.946
_diffrn_reflns_Laue_measured_fraction_full 0.955
_diffrn_reflns_point_group_measured_fraction_max 0.819
_diffrn_reflns_point_group_measured_fraction_full 0.830
_reflns_number_total             3006
_reflns_number_gt                2717
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.507
_reflns_Friedel_fraction_max     0.647
_reflns_Friedel_fraction_full    0.660

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

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
__computing_structure_solution   'SIR-92 (Altomare, 1994)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  
;
'WinGX publication routines (Farrugia, 1999), (Farrugia, 2012)'
;
_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)+(0.0357P)²+0.6707P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 817 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.012(19)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3006
_refine_ls_number_parameters     230
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0467
_refine_ls_R_factor_gt           0.0407
_refine_ls_wR_factor_ref         0.0953
_refine_ls_wR_factor_gt          0.0920
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_restrained_S_all      1.068
_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 0.8638(9) 0.0698(9) 0.3871(4) 0.0476(19) Uani 1 1 d . . . . .
C2 C 0.7450(10) 0.0453(9) 0.4285(5) 0.056(2) Uani 1 1 d . . . . .
C3 C 0.7283(15) -0.0776(11) 0.4553(6) 0.077(3) Uani 1 1 d . . . . .
H3 H 0.6476 -0.0969 0.4805 0.093 Uiso 1 1 calc R U . . .
C4 C 0.8298(19) -0.1691(10) 0.4446(6) 0.087(4) Uani 1 1 d . . . . .
H4 H 0.8191 -0.2489 0.4638 0.105 Uiso 1 1 calc R U . . .
C5 C 0.9459(15) -0.1428(11) 0.4058(6) 0.079(3) Uani 1 1 d . . . . .
H5 H 1.0152 -0.2044 0.3994 0.095 Uiso 1 1 calc R U . . .
C6 C 0.9618(12) -0.0267(10) 0.3761(5) 0.063(2) Uani 1 1 d . . . . .
H6 H 1.0397 -0.0119 0.3481 0.075 Uiso 1 1 calc R U . . .
C7 C 0.6387(9) 0.1373(11) 0.4486(4) 0.056(2) Uani 1 1 d . . . . .
C8 C 0.7777(8) 0.2223(9) 0.2711(4) 0.0474(19) Uani 1 1 d . . . . .
C9 C 0.7414(11) 0.1135(13) 0.2380(5) 0.070(3) Uani 1 1 d . . . . .
H9 H 0.7649 0.0353 0.2564 0.084 Uiso 1 1 calc R U . . .
C10 C 0.6682(13) 0.1202(16) 0.1758(5) 0.086(4) Uani 1 1 d . . . . .
H10 H 0.6418 0.0465 0.1533 0.103 Uiso 1 1 calc R U . . .
C11 C 0.6359(12) 0.2361(17) 0.1486(5) 0.083(4) Uani 1 1 d . . . . .
H11 H 0.5884 0.2405 0.1073 0.100 Uiso 1 1 calc R U . . .
C12 C 0.6725(14) 0.3445(14) 0.1812(5) 0.082(3) Uani 1 1 d . . . . .
H12 H 0.6498 0.4225 0.1622 0.098 Uiso 1 1 calc R U . . .
C13 C 0.7441(10) 0.3387(11) 0.2430(5) 0.065(3) Uani 1 1 d . . . . .
H13 H 0.7694 0.4129 0.2653 0.077 Uiso 1 1 calc R U . . .
C14 C 1.0691(9) 0.2228(9) 0.3181(4) 0.0476(19) Uani 1 1 d . . . . .
C15 C 1.1049(10) 0.2039(11) 0.2513(5) 0.061(2) Uani 1 1 d . . . . .
H15 H 1.0333 0.1916 0.2194 0.074 Uiso 1 1 calc R U . . .
C16 C 1.2458(12) 0.2028(15) 0.2307(6) 0.087(4) Uani 1 1 d . . . . .
H16 H 1.2682 0.1890 0.1854 0.104 Uiso 1 1 calc R U . . .
C17 C 1.3527(11) 0.2223(13) 0.2773(7) 0.080(3) Uani 1 1 d . . . . .
H17 H 1.4477 0.2229 0.2640 0.096 Uiso 1 1 calc R U . . .
C18 C 1.3164(12) 0.2407(13) 0.3433(7) 0.082(3) Uani 1 1 d . . . . .
H18 H 1.3881 0.2540 0.3750 0.099 Uiso 1 1 calc R U . . .
C19 C 1.1774(12) 0.2403(11) 0.3645(5) 0.069(3) Uani 1 1 d . . . . .
H19 H 1.1561 0.2517 0.4101 0.083 Uiso 1 1 calc R U . . .
N1 N 0.6567(7) 0.2562(8) 0.4491(3) 0.0519(17) Uani 1 1 d . . . . .
O1 O 0.5378(7) 0.3226(8) 0.4717(4) 0.071(2) Uani 1 1 d . . . . .
H1 H 0.5548 0.3987 0.4711 0.107 Uiso 1 1 calc R U . . .
P1 P 0.8876(2) 0.2217(2) 0.34680(10) 0.0432(5) Uani 1 1 d . . . . .
Cl1 Cl 0.7547(4) 0.5155(3) 0.50601(15) 0.0859(9) Uani 1 1 d . . . . .
Cl2 Cl 0.9996(3) 0.5014(3) 0.38641(14) 0.0686(6) Uani 1 1 d . . . . .
Pd1 Pd 0.82285(6) 0.36955(6) 0.42059(3) 0.04614(19) Uani 1 1 d . . . . .
H7 H 0.550(10) 0.108(9) 0.464(4) 0.05(2) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C6 1.391(14) . ?
C1 C2 1.407(12) . ?
C1 P1 1.805(10) . ?
C2 C3 1.411(16) . ?
C2 C7 1.450(15) . ?
C3 C4 1.37(2) . ?
C3 H3 0.9300 . ?
C4 C5 1.362(19) . ?
C4 H4 0.9300 . ?
C5 C6 1.368(17) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 N1 1.268(14) . ?
C7 H7 0.94(9) . ?
C8 C9 1.366(15) . ?
C8 C13 1.386(14) . ?
C8 P1 1.816(8) . ?
C9 C10 1.409(14) . ?
C9 H9 0.9300 . ?
C10 C11 1.37(2) . ?
C10 H10 0.9300 . ?
C11 C12 1.36(2) . ?
C11 H11 0.9300 . ?
C12 C13 1.395(15) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C14 C15 1.376(12) . ?
C14 C19 1.382(13) . ?
C14 P1 1.797(9) . ?
C15 C16 1.384(13) . ?
C15 H15 0.9300 . ?
C16 C17 1.379(17) . ?
C16 H16 0.9300 . ?
C17 C18 1.359(18) . ?
C17 H17 0.9300 . ?
C18 C19 1.371(16) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?
N1 O1 1.393(10) . ?
N1 Pd1 2.046(8) . ?
O1 H1 0.8200 . ?
P1 Pd1 2.221(2) . ?
Cl1 Pd1 2.373(3) . ?
Cl2 Pd1 2.270(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 C1 C2 118.7(9) . . ?
C6 C1 P1 120.1(7) . . ?
C2 C1 P1 121.2(7) . . ?
C1 C2 C3 118.4(10) . . ?
C1 C2 C7 125.6(9) . . ?
C3 C2 C7 116.0(9) . . ?
C4 C3 C2 120.9(11) . . ?
C4 C3 H3 119.5 . . ?
C2 C3 H3 119.5 . . ?
C5 C4 C3 119.9(10) . . ?
C5 C4 H4 120.1 . . ?
C3 C4 H4 120.1 . . ?
C4 C5 C6 120.7(11) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 H5 119.6 . . ?
C5 C6 C1 121.3(11) . . ?
C5 C6 H6 119.3 . . ?
C1 C6 H6 119.3 . . ?
N1 C7 C2 125.1(8) . . ?
N1 C7 H7 116(6) . . ?
C2 C7 H7 119(6) . . ?
C9 C8 C13 120.0(8) . . ?
C9 C8 P1 122.1(7) . . ?
C13 C8 P1 117.5(7) . . ?
C8 C9 C10 119.7(11) . . ?
C8 C9 H9 120.1 . . ?
C10 C9 H9 120.1 . . ?
C11 C10 C9 119.6(12) . . ?
C11 C10 H10 120.2 . . ?
C9 C10 H10 120.2 . . ?
C12 C11 C10 120.8(10) . . ?
C12 C11 H11 119.6 . . ?
C10 C11 H11 119.6 . . ?
C11 C12 C13 120.0(12) . . ?
C11 C12 H12 120.0 . . ?
C13 C12 H12 120.0 . . ?
C8 C13 C12 119.9(11) . . ?
C8 C13 H13 120.0 . . ?
C12 C13 H13 120.0 . . ?
C15 C14 C19 118.4(9) . . ?
C15 C14 P1 122.2(7) . . ?
C19 C14 P1 119.4(7) . . ?
C14 C15 C16 121.1(10) . . ?
C14 C15 H15 119.5 . . ?
C16 C15 H15 119.5 . . ?
C17 C16 C15 120.0(10) . . ?
C17 C16 H16 120.0 . . ?
C15 C16 H16 120.0 . . ?
C18 C17 C16 118.6(10) . . ?
C18 C17 H17 120.7 . . ?
C16 C17 H17 120.7 . . ?
C17 C18 C19 122.1(11) . . ?
C17 C18 H18 119.0 . . ?
C19 C18 H18 119.0 . . ?
C18 C19 C14 119.9(10) . . ?
C18 C19 H19 120.0 . . ?
C14 C19 H19 120.0 . . ?
C7 N1 O1 113.2(7) . . ?
C7 N1 Pd1 132.8(6) . . ?
O1 N1 Pd1 113.9(6) . . ?
N1 O1 H1 109.5 . . ?
C14 P1 C1 105.2(4) . . ?
C14 P1 C8 106.3(4) . . ?
C1 P1 C8 107.2(4) . . ?
C14 P1 Pd1 117.5(3) . . ?
C1 P1 Pd1 107.7(3) . . ?
C8 P1 Pd1 112.4(3) . . ?
N1 Pd1 P1 88.7(2) . . ?
N1 Pd1 Cl2 177.3(2) . . ?
P1 Pd1 Cl2 92.12(9) . . ?
N1 Pd1 Cl1 88.8(2) . . ?
P1 Pd1 Cl1 175.59(10) . . ?
Cl2 Pd1 Cl1 90.55(10) . . ?

_refine_diff_density_max         0.919
_refine_diff_density_min         -0.555
_refine_diff_density_rms         0.089

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

data_2
_database_code_depnum_ccdc_archive 'CCDC 1054277'
_audit_update_record             
;
2015-03-16 deposited with the CCDC.
2015-05-19 downloaded from the CCDC.
;
#============================================================================= 

_audit_creation_method           
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET)
(compiled Aug 27 2010,11:50:40)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C38 H32 N2 O2 P2 Pd, 2(Cl)'
_chemical_formula_sum            'C38 H32 Cl2 N2 O2 P2 Pd'
_chemical_formula_weight         787.89

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'
P P 0.1023 0.0942 '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      orthorhombic
_space_group_IT_number           43
_space_group_name_H-M_alt        'F 2 d d'
_space_group_name_Hall           'F -2d 2'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'x+1/4, y+1/4, -z+1/4'
'x, -y, -z'
'x+1/4, -y+1/4, z+1/4'
'x, y+1/2, z+1/2'
'x+1/4, y+3/4, -z+3/4'
'x, -y+1/2, -z+1/2'
'x+1/4, -y+3/4, z+3/4'
'x+1/2, y, z+1/2'
'x+3/4, y+1/4, -z+3/4'
'x+1/2, -y, -z+1/2'
'x+3/4, -y+1/4, z+3/4'
'x+1/2, y+1/2, z'
'x+3/4, y+3/4, -z+1/4'
'x+1/2, -y+1/2, -z'
'x+3/4, -y+3/4, z+1/4'

_cell_length_a                   10.2329(6)
_cell_length_b                   21.5082(12)
_cell_length_c                   31.0365(18)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     6830.9(7)
_cell_formula_units_Z            8
_cell_measurement_temperature    123.8
_cell_measurement_reflns_used    11599
_cell_measurement_theta_min      2.9498
_cell_measurement_theta_max      27.7091

_exptl_crystal_description       prism
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.532
_exptl_crystal_F_000             3200
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.04
_exptl_absorpt_coefficient_mu    0.831
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.90203
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET)
(compiled Aug 27 2010,11:50:40)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      123.8
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 16.0727
_diffrn_reflns_number            19091
_diffrn_reflns_av_unetI/netI     0.0272
_diffrn_reflns_av_R_equivalents  0.0308
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_l_min       -40
_diffrn_reflns_limit_l_max       39
_diffrn_reflns_theta_min         2.956
_diffrn_reflns_theta_max         27.770
_diffrn_reflns_theta_full        24.970
_diffrn_measured_fraction_theta_max 0.962
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.962
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.964
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3744
_reflns_number_gt                3595
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.898
_reflns_Friedel_fraction_max     0.966
_reflns_Friedel_fraction_full    0.999

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

_computing_data_collection       
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET)
(compiled Aug 27 2010,11:50:40)
;
_computing_cell_refinement       
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET)
(compiled Aug 27 2010,11:50:40)
;
_computing_data_reduction        
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET)
(compiled Aug 27 2010,11:50:40)
;
_computing_structure_solution    'SIR2004(Burla, 2005)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  
;
'WinGX publication routines (Farrugia, 1999), (Farrugia, 2012)'
;
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0222P)²+9.7014P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   -0.02(3)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3744
_refine_ls_number_parameters     218
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0243
_refine_ls_R_factor_gt           0.0220
_refine_ls_wR_factor_ref         0.0503
_refine_ls_wR_factor_gt          0.0492
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_restrained_S_all      1.052
_refine_ls_shift/su_max          0.002
_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 2.0438(4) 1.25734(15) 1.14550(12) 0.0190(8) Uani 1 1 d . . . . .
C2 C 1.9126(4) 1.24066(16) 1.13686(13) 0.0203(8) Uani 1 1 d . . . . .
C3 C 1.8609(3) 1.25312(14) 1.09611(11) 0.0260(8) Uani 1 1 d . . . . .
H3 H 1.7771 1.2396 1.0893 0.031 Uiso 1 1 calc R U . . .
C4 C 1.9327(4) 1.28529(16) 1.06578(11) 0.0282(8) Uani 1 1 d . . . . .
H4 H 1.8951 1.2956 1.0394 0.034 Uiso 1 1 calc R U . . .
C5 C 2.0593(3) 1.30218(15) 1.07440(11) 0.0257(7) Uani 1 1 d . . . . .
H5 H 2.1076 1.3236 1.0538 0.031 Uiso 1 1 calc R U . . .
C6 C 2.1159(3) 1.28735(14) 1.11394(10) 0.0216(6) Uani 1 1 d . . . . .
H6 H 2.2027 1.2977 1.1192 0.026 Uiso 1 1 calc R U . . .
C7 C 1.8252(3) 1.21066(14) 1.16714(11) 0.0221(7) Uani 1 1 d . . . . .
C8 C 2.1716(3) 1.15466(14) 1.18741(10) 0.0208(7) Uani 1 1 d . . . . .
C9 C 2.1173(4) 1.10811(16) 1.21265(11) 0.0280(8) Uani 1 1 d . . . . .
H9 H 2.0573 1.1178 1.2341 0.034 Uiso 1 1 calc R U . . .
C10 C 2.1538(4) 1.04694(16) 1.20539(13) 0.0383(10) Uani 1 1 d . . . . .
H10 H 2.1162 1.0153 1.2216 0.046 Uiso 1 1 calc R U . . .
C11 C 2.2452(5) 1.03242(17) 1.17439(12) 0.0421(11) Uani 1 1 d . . . . .
H11 H 2.2710 0.9913 1.1705 0.051 Uiso 1 1 calc R U . . .
C12 C 2.2986(4) 1.07835(17) 1.14910(12) 0.0384(10) Uani 1 1 d . . . . .
H12 H 2.3602 1.0684 1.1282 0.046 Uiso 1 1 calc R U . . .
C13 C 2.2603(3) 1.13925(16) 1.15499(10) 0.0286(8) Uani 1 1 d . . . . .
H13 H 2.2938 1.1702 1.1372 0.034 Uiso 1 1 calc R U . . .
C14 C 2.2694(3) 1.28216(14) 1.19822(9) 0.0168(6) Uani 1 1 d . . . . .
C15 C 2.3946(3) 1.25682(15) 1.20149(10) 0.0197(6) Uani 1 1 d . . . . .
H15 H 2.4060 1.2139 1.2011 0.024 Uiso 1 1 calc R U . . .
C16 C 2.5023(3) 1.29578(16) 1.20532(10) 0.0239(7) Uani 1 1 d . . . . .
H16 H 2.5857 1.2788 1.2073 0.029 Uiso 1 1 calc R U . . .
C17 C 2.4865(4) 1.35946(15) 1.20616(10) 0.0257(7) Uani 1 1 d . . . . .
H17 H 2.5588 1.3853 1.2090 0.031 Uiso 1 1 calc R U . . .
C18 C 2.3623(4) 1.38484(16) 1.20271(11) 0.0267(7) Uani 1 1 d . . . . .
H18 H 2.3517 1.4278 1.2030 0.032 Uiso 1 1 calc R U . . .
C19 C 2.2540(3) 1.34669(15) 1.19891(10) 0.0224(7) Uani 1 1 d . . . . .
H19 H 2.1710 1.3640 1.1968 0.027 Uiso 1 1 calc R U . . .
Cl1 Cl 1.87462(10) 1.12324(4) 1.30153(3) 0.0360(2) Uani 1 1 d . . . . .
N1 N 1.8378(2) 1.21149(12) 1.20799(9) 0.0204(6) Uani 1 1 d . . . . .
O1 O 1.7376(2) 1.18033(10) 1.22909(7) 0.0260(5) Uani 1 1 d . . . . .
H1 H 1.7496 1.1820 1.2552 0.039 Uiso 1 1 calc R U . . .
P1 P 2.12332(8) 1.23477(4) 1.19619(2) 0.01634(16) Uani 1 1 d . . . . .
Pd1 Pd 1.97854(3) 1.2500 1.2500 0.01729(8) Uani 1 2 d S T P . .
H7 H 1.761(4) 1.1905(17) 1.1560(10) 0.024(9) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C6 1.386(5) . ?
C1 C2 1.415(4) . ?
C1 P1 1.837(4) . ?
C2 C3 1.397(5) . ?
C2 C7 1.449(5) . ?
C3 C4 1.380(5) . ?
C4 C5 1.372(5) . ?
C5 C6 1.394(4) . ?
C7 N1 1.275(4) . ?
C8 C9 1.387(5) . ?
C8 C13 1.395(5) . ?
C8 P1 1.813(3) . ?
C9 C10 1.386(5) . ?
C10 C11 1.378(6) . ?
C11 C12 1.375(6) . ?
C12 C13 1.379(5) . ?
C14 C15 1.397(4) . ?
C14 C19 1.397(4) . ?
C14 P1 1.810(3) . ?
C15 C16 1.389(5) . ?
C16 C17 1.379(5) . ?
C17 C18 1.388(5) . ?
C18 C19 1.383(5) . ?
N1 O1 1.389(3) . ?
N1 Pd1 2.112(3) . ?
P1 Pd1 2.2564(8) . ?
Pd1 N1 2.112(3) 7_577 ?
Pd1 P1 2.2564(8) 7_577 ?

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
C6 C1 C2 119.3(4) . . ?
C6 C1 P1 119.5(3) . . ?
C2 C1 P1 121.1(3) . . ?
C3 C2 C1 118.9(4) . . ?
C3 C2 C7 116.0(3) . . ?
C1 C2 C7 125.1(4) . . ?
C4 C3 C2 120.8(3) . . ?
C5 C4 C3 120.1(3) . . ?
C4 C5 C6 120.2(3) . . ?
C1 C6 C5 120.5(3) . . ?
N1 C7 C2 125.2(3) . . ?
C9 C8 C13 119.8(3) . . ?
C9 C8 P1 119.5(3) . . ?
C13 C8 P1 120.8(3) . . ?
C10 C9 C8 119.0(4) . . ?
C11 C10 C9 120.8(4) . . ?
C12 C11 C10 120.4(3) . . ?
C11 C12 C13 119.6(4) . . ?
C12 C13 C8 120.4(4) . . ?
C15 C14 C19 119.3(3) . . ?
C15 C14 P1 122.7(2) . . ?
C19 C14 P1 117.8(2) . . ?
C16 C15 C14 119.9(3) . . ?
C17 C16 C15 120.5(3) . . ?
C16 C17 C18 119.8(3) . . ?
C19 C18 C17 120.4(3) . . ?
C18 C19 C14 120.0(3) . . ?
C7 N1 O1 112.8(3) . . ?
C7 N1 Pd1 133.5(2) . . ?
O1 N1 Pd1 113.69(18) . . ?
C14 P1 C8 108.40(14) . . ?
C14 P1 C1 104.29(16) . . ?
C8 P1 C1 104.08(15) . . ?
C14 P1 Pd1 115.76(10) . . ?
C8 P1 Pd1 115.34(11) . . ?
C1 P1 Pd1 107.73(14) . . ?
N1 Pd1 N1 94.02(14) 7_577 . ?
N1 Pd1 P1 164.08(7) 7_577 . ?
N1 Pd1 P1 86.20(7) . . ?
N1 Pd1 P1 86.20(7) 7_577 7_577 ?
N1 Pd1 P1 164.08(7) . 7_577 ?
P1 Pd1 P1 97.92(4) . 7_577 ?

_refine_diff_density_max         0.431
_refine_diff_density_min         -0.343
_refine_diff_density_rms         0.054

