# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2017

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

data_rn821m
_audit_block_doi                 10.5517/ccdc.csd.cc1n5d4c
_database_code_depnum_ccdc_archive 'CCDC 1524522'
_audit_update_record             
;
2016-12-26 deposited with the CCDC.
2017-07-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C28 H24 N2 O2 Se'
_chemical_formula_sum            'C28 H24 N2 O2 Se'
_chemical_formula_weight         499.45

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'
Se Se -0.0929 2.2259 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_space_group_name_Hall  '-P 2yn'

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

_cell_length_a                   9.341(6)
_cell_length_b                   20.608(13)
_cell_length_c                   13.101(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 109.331(11)
_cell_angle_gamma                90.00
_cell_volume                     2380(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    3008
_cell_measurement_theta_min      2.55
_cell_measurement_theta_max      19.45

_exptl_crystal_description       block
_exptl_crystal_colour            white
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.29
_exptl_crystal_density_meas      1.394
_exptl_crystal_density_diffrn    1.394
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1024
_exptl_absorpt_coefficient_mu    1.605
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.602
_exptl_absorpt_correction_T_max  0.626
_exptl_absorpt_process_details   '(SADABS; Bruker, 2000)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            22425
_diffrn_reflns_av_R_equivalents  0.0618
_diffrn_reflns_av_sigmaI/netI    0.0467
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.92
_diffrn_reflns_theta_max         25.00
_reflns_number_total             4166
_reflns_number_gt                2835
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0595P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4166
_refine_ls_number_parameters     298
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0723
_refine_ls_R_factor_gt           0.0416
_refine_ls_wR_factor_ref         0.1137
_refine_ls_wR_factor_gt          0.0937
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_restrained_S_all      1.010
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Se1 Se 0.31402(4) 0.072149(19) 0.76674(3) 0.06248(17) Uani 1 1 d . . .
C13 C 0.0734(4) 0.06741(15) 0.5667(2) 0.0460(8) Uani 1 1 d . . .
N2 N 0.2209(3) 0.01219(12) 1.0022(2) 0.0488(7) Uani 1 1 d . . .
C23 C 0.2704(4) 0.07091(15) 1.0644(2) 0.0464(8) Uani 1 1 d . . .
N1 N 0.1116(3) 0.10818(12) 0.4970(2) 0.0462(6) Uani 1 1 d . . .
C7 C 0.2567(4) 0.10683(15) 0.4803(2) 0.0456(8) Uani 1 1 d . . .
C6 C 0.0036(4) 0.15479(15) 0.4337(3) 0.0447(8) Uani 1 1 d . . .
C12 C 0.3599(4) 0.15591(17) 0.5226(3) 0.0623(10) Uani 1 1 d . . .
H12 H 0.3365 0.1891 0.5625 0.075 Uiso 1 1 calc R . .
C8 C 0.2924(4) 0.05816(16) 0.4207(3) 0.0531(9) Uani 1 1 d . . .
H8 H 0.2231 0.0251 0.3915 0.064 Uiso 1 1 calc R . .
C5 C -0.0262(4) 0.15698(17) 0.3235(3) 0.0559(9) Uani 1 1 d . . .
H5 H 0.0209 0.1280 0.2904 0.067 Uiso 1 1 calc R . .
C9 C 0.4309(4) 0.05845(19) 0.4045(3) 0.0638(10) Uani 1 1 d . . .
H9 H 0.4545 0.0255 0.3642 0.077 Uiso 1 1 calc R . .
C16 C 0.1508(4) 0.01410(17) 0.8919(3) 0.0531(9) Uani 1 1 d . . .
C17 C 0.2423(4) -0.04790(16) 1.0614(3) 0.0477(8) Uani 1 1 d . . .
C25 C 0.2191(5) 0.16891(17) 1.1426(3) 0.0705(11) Uani 1 1 d . . .
H25 H 0.1499 0.1983 1.1534 0.085 Uiso 1 1 calc R . .
C24 C 0.1684(4) 0.11369(16) 1.0809(3) 0.0575(9) Uani 1 1 d . . .
H24 H 0.0649 0.1057 1.0507 0.069 Uiso 1 1 calc R . .
C18 C 0.2260(4) -0.04873(18) 1.1622(3) 0.0580(9) Uani 1 1 d . . .
H18 H 0.1983 -0.0111 1.1902 0.070 Uiso 1 1 calc R . .
C22 C 0.2843(4) -0.10421(17) 1.0211(3) 0.0615(10) Uani 1 1 d . . .
H22 H 0.2953 -0.1041 0.9531 0.074 Uiso 1 1 calc R . .
C1 C -0.0688(4) 0.19770(17) 0.4815(3) 0.0622(10) Uani 1 1 d . . .
H1 H -0.0492 0.1964 0.5559 0.075 Uiso 1 1 calc R . .
C28 C 0.4235(4) 0.08248(17) 1.1101(3) 0.0618(10) Uani 1 1 d . . .
H28 H 0.4931 0.0532 1.0996 0.074 Uiso 1 1 calc R . .
C4 C -0.1265(4) 0.20266(19) 0.2628(3) 0.0667(10) Uani 1 1 d . . .
H4 H -0.1457 0.2045 0.1885 0.080 Uiso 1 1 calc R . .
C11 C 0.4987(5) 0.1556(2) 0.5052(3) 0.0716(11) Uani 1 1 d . . .
H11 H 0.5680 0.1888 0.5333 0.086 Uiso 1 1 calc R . .
C10 C 0.5341(4) 0.1069(2) 0.4472(3) 0.0685(11) Uani 1 1 d . . .
H10 H 0.6278 0.1065 0.4368 0.082 Uiso 1 1 calc R . .
C3 C -0.1982(4) 0.24522(18) 0.3096(4) 0.0711(11) Uani 1 1 d . . .
H3 H -0.2656 0.2758 0.2677 0.085 Uiso 1 1 calc R . .
C2 C -0.1697(5) 0.24232(18) 0.4192(3) 0.0708(11) Uani 1 1 d . . .
H2 H -0.2189 0.2708 0.4516 0.085 Uiso 1 1 calc R . .
C27 C 0.4736(5) 0.1373(2) 1.1714(3) 0.0792(12) Uani 1 1 d . . .
H27 H 0.5770 0.1453 1.2017 0.095 Uiso 1 1 calc R . .
C21 C 0.3098(5) -0.16028(19) 1.0814(4) 0.0790(12) Uani 1 1 d . . .
H21 H 0.3384 -0.1980 1.0543 0.095 Uiso 1 1 calc R . .
C20 C 0.2932(5) -0.1607(2) 1.1815(4) 0.0850(13) Uani 1 1 d . . .
H20 H 0.3108 -0.1987 1.2220 0.102 Uiso 1 1 calc R . .
C19 C 0.2511(5) -0.1057(2) 1.2219(3) 0.0734(11) Uani 1 1 d . . .
H19 H 0.2392 -0.1064 1.2896 0.088 Uiso 1 1 calc R . .
C26 C 0.3714(6) 0.1799(2) 1.1875(3) 0.0773(12) Uani 1 1 d . . .
H26 H 0.4056 0.2168 1.2295 0.093 Uiso 1 1 calc R . .
O1 O -0.0534(3) 0.06733(11) 0.57458(19) 0.0589(6) Uani 1 1 d . . .
O2 O 0.0910(3) -0.03378(12) 0.84126(19) 0.0691(7) Uani 1 1 d . . .
C15 C 0.1565(5) 0.07680(16) 0.8348(3) 0.0622(10) Uani 1 1 d . . .
H15A H 0.1783 0.1123 0.8863 0.075 Uiso 1 1 calc R . .
H15B H 0.0589 0.0850 0.7802 0.075 Uiso 1 1 calc R . .
C14 C 0.1956(4) 0.02435(15) 0.6380(2) 0.0514(8) Uani 1 1 d . . .
H14A H 0.2613 0.0097 0.5988 0.062 Uiso 1 1 calc R . .
H14B H 0.1501 -0.0135 0.6590 0.062 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
Se1 C14 1.950(3) . ?
Se1 C15 1.959(4) . ?
C13 O1 1.222(4) . ?
C13 N1 1.372(4) . ?
C13 C14 1.502(4) . ?
N2 C16 1.375(4) . ?
N2 C17 1.440(4) . ?
N2 C23 1.446(4) . ?
C23 C24 1.367(5) . ?
C23 C28 1.376(5) . ?
N1 C6 1.440(4) . ?
N1 C7 1.443(4) . ?
C7 C8 1.378(4) . ?
C7 C12 1.380(4) . ?
C6 C5 1.378(4) . ?
C6 C1 1.383(4) . ?
C12 C11 1.389(5) . ?
C8 C9 1.379(5) . ?
C5 C4 1.380(5) . ?
C9 C10 1.372(5) . ?
C16 O2 1.217(4) . ?
C16 C15 1.503(5) . ?
C17 C18 1.378(5) . ?
C17 C22 1.384(5) . ?
C25 C26 1.366(6) . ?
C25 C24 1.385(5) . ?
C18 C19 1.387(5) . ?
C22 C21 1.376(5) . ?
C1 C2 1.375(5) . ?
C28 C27 1.375(5) . ?
C4 C3 1.366(5) . ?
C11 C10 1.364(5) . ?
C3 C2 1.372(5) . ?
C27 C26 1.365(6) . ?
C21 C20 1.370(6) . ?
C20 C19 1.363(6) . ?

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
C14 Se1 C15 96.99(15) . . ?
O1 C13 N1 122.0(3) . . ?
O1 C13 C14 120.3(3) . . ?
N1 C13 C14 117.7(3) . . ?
C16 N2 C17 121.6(3) . . ?
C16 N2 C23 121.3(3) . . ?
C17 N2 C23 117.1(3) . . ?
C24 C23 C28 119.9(3) . . ?
C24 C23 N2 121.3(3) . . ?
C28 C23 N2 118.9(3) . . ?
C13 N1 C6 120.3(3) . . ?
C13 N1 C7 123.5(3) . . ?
C6 N1 C7 116.1(2) . . ?
C8 C7 C12 119.5(3) . . ?
C8 C7 N1 121.0(3) . . ?
C12 C7 N1 119.5(3) . . ?
C5 C6 C1 119.6(3) . . ?
C5 C6 N1 119.0(3) . . ?
C1 C6 N1 121.4(3) . . ?
C7 C12 C11 119.8(3) . . ?
C7 C8 C9 120.0(3) . . ?
C6 C5 C4 119.3(3) . . ?
C10 C9 C8 120.6(3) . . ?
O2 C16 N2 121.5(3) . . ?
O2 C16 C15 120.8(3) . . ?
N2 C16 C15 117.7(3) . . ?
C18 C17 C22 119.3(3) . . ?
C18 C17 N2 119.1(3) . . ?
C22 C17 N2 121.5(3) . . ?
C26 C25 C24 119.6(4) . . ?
C23 C24 C25 120.0(4) . . ?
C17 C18 C19 119.9(4) . . ?
C21 C22 C17 120.1(3) . . ?
C2 C1 C6 120.0(3) . . ?
C27 C28 C23 120.0(4) . . ?
C3 C4 C5 121.3(4) . . ?
C10 C11 C12 120.4(4) . . ?
C11 C10 C9 119.7(4) . . ?
C4 C3 C2 119.2(4) . . ?
C3 C2 C1 120.5(4) . . ?
C26 C27 C28 119.9(4) . . ?
C20 C21 C22 120.1(4) . . ?
C19 C20 C21 120.3(4) . . ?
C20 C19 C18 120.1(4) . . ?
C27 C26 C25 120.6(4) . . ?
C16 C15 Se1 109.9(2) . . ?
C13 C14 Se1 109.7(2) . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.316
_refine_diff_density_min         -0.337
_refine_diff_density_rms         0.123
####################################################################### 
# 
# 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_pj826m
_audit_block_doi                 10.5517/ccdc.csd.cc1n5d29
_database_code_depnum_ccdc_archive 'CCDC 1524520'
_audit_update_record             
;
2016-12-26 deposited with the CCDC.
2017-07-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H12 Br N O'
_chemical_formula_sum            'C14 H12 Br N O'
_chemical_formula_weight         290.15

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

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_space_group_name_Hall  '-P 2yn'

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

_cell_length_a                   9.398(3)
_cell_length_b                   13.898(4)
_cell_length_c                   10.247(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 112.460(6)
_cell_angle_gamma                90.00
_cell_volume                     1236.9(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    1252
_cell_measurement_theta_min      2.60
_cell_measurement_theta_max      17.81

_exptl_crystal_description       block
_exptl_crystal_colour            white
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.25
_exptl_crystal_density_meas      1.558
_exptl_crystal_density_diffrn    1.558
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             584.0
_exptl_absorpt_coefficient_mu    3.305
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.403
_exptl_absorpt_correction_T_max  0.432
_exptl_absorpt_process_details   '(SADABS; Bruker, 2000)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            11687
_diffrn_reflns_av_R_equivalents  0.0625
_diffrn_reflns_av_sigmaI/netI    0.0587
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.50
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2175
_reflns_number_gt                1379
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0349P)²+0.6788P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2173
_refine_ls_number_parameters     154
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0879
_refine_ls_R_factor_gt           0.0468
_refine_ls_wR_factor_ref         0.1100
_refine_ls_wR_factor_gt          0.0965
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_restrained_S_all      1.024
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 1.05699(6) 0.00227(4) 0.69706(6) 0.0809(2) Uani 1 1 d . . .
O1 O 0.8040(3) 0.0443(2) 0.8648(3) 0.0618(8) Uani 1 1 d . . .
N1 N 0.7862(3) 0.1660(2) 0.7114(3) 0.0399(7) Uani 1 1 d . . .
C7 C 0.8605(4) 0.2323(3) 0.6491(4) 0.0399(9) Uani 1 1 d . . .
C6 C 0.6216(4) 0.1722(3) 0.6610(4) 0.0407(9) Uani 1 1 d . . .
C13 C 0.8661(5) 0.0970(3) 0.8079(4) 0.0459(10) Uani 1 1 d . . .
C5 C 0.5515(5) 0.2611(3) 0.6399(4) 0.0517(11) Uani 1 1 d . . .
H5 H 0.6107 0.3169 0.6632 0.062 Uiso 1 1 calc R . .
C3 C 0.3047(5) 0.1852(4) 0.5498(5) 0.0634(12) Uani 1 1 d . . .
H3 H 0.1978 0.1892 0.5115 0.076 Uiso 1 1 calc R . .
C11 C 0.9101(5) 0.2839(4) 0.4486(5) 0.0637(13) Uani 1 1 d . . .
H11 H 0.8987 0.2751 0.3551 0.076 Uiso 1 1 calc R . .
C4 C 0.3914(5) 0.2671(4) 0.5834(4) 0.0589(12) Uani 1 1 d . . .
H4 H 0.3435 0.3270 0.5686 0.071 Uiso 1 1 calc R . .
C2 C 0.3750(5) 0.0974(3) 0.5723(5) 0.0625(12) Uani 1 1 d . . .
H2 H 0.3153 0.0419 0.5500 0.075 Uiso 1 1 calc R . .
C14 C 1.0349(4) 0.0866(3) 0.8391(4) 0.0554(11) Uani 1 1 d . . .
H14A H 1.0873 0.0594 0.9325 0.067 Uiso 1 1 calc R . .
H14B H 1.0798 0.1491 0.8362 0.067 Uiso 1 1 calc R . .
C12 C 0.8448(4) 0.2195(3) 0.5117(4) 0.0491(10) Uani 1 1 d . . .
H12 H 0.7899 0.1670 0.4608 0.059 Uiso 1 1 calc R . .
C1 C 0.5331(5) 0.0899(3) 0.6276(4) 0.0530(11) Uani 1 1 d . . .
H1 H 0.5798 0.0297 0.6424 0.064 Uiso 1 1 calc R . .
C8 C 0.9407(5) 0.3102(3) 0.7231(4) 0.0550(11) Uani 1 1 d . . .
H8 H 0.9498 0.3203 0.8157 0.066 Uiso 1 1 calc R . .
C10 C 0.9916(5) 0.3608(4) 0.5235(6) 0.0674(14) Uani 1 1 d . . .
H10 H 1.0359 0.4042 0.4811 0.081 Uiso 1 1 calc R . .
C9 C 1.0082(5) 0.3740(3) 0.6602(5) 0.0657(13) Uani 1 1 d . . .
H9 H 1.0649 0.4258 0.7114 0.079 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
Br1 C14 1.941(4) . ?
O1 C13 1.215(4) . ?
N1 C13 1.377(5) . ?
N1 C6 1.434(4) . ?
N1 C7 1.443(4) . ?
C7 C12 1.370(5) . ?
C7 C8 1.372(5) . ?
C6 C5 1.378(5) . ?
C6 C1 1.379(5) . ?
C13 C14 1.501(6) . ?
C5 C4 1.393(5) . ?
C3 C2 1.365(6) . ?
C3 C4 1.365(6) . ?
C11 C10 1.367(7) . ?
C11 C12 1.379(6) . ?
C2 C1 1.376(5) . ?
C8 C9 1.383(6) . ?
C10 C9 1.361(6) . ?

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
C13 N1 C6 121.2(3) . . ?
C13 N1 C7 122.6(3) . . ?
C6 N1 C7 116.1(3) . . ?
C12 C7 C8 119.4(4) . . ?
C12 C7 N1 119.4(3) . . ?
C8 C7 N1 121.1(3) . . ?
C5 C6 C1 119.9(4) . . ?
C5 C6 N1 119.7(3) . . ?
C1 C6 N1 120.3(3) . . ?
O1 C13 N1 122.3(4) . . ?
O1 C13 C14 120.1(4) . . ?
N1 C13 C14 117.5(4) . . ?
C6 C5 C4 119.6(4) . . ?
C2 C3 C4 119.9(4) . . ?
C10 C11 C12 119.9(4) . . ?
C3 C4 C5 120.0(4) . . ?
C3 C2 C1 121.0(4) . . ?
C13 C14 Br1 107.8(3) . . ?
C7 C12 C11 120.4(4) . . ?
C2 C1 C6 119.5(4) . . ?
C7 C8 C9 120.1(4) . . ?
C9 C10 C11 120.2(4) . . ?
C10 C9 C8 120.0(4) . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.545
_refine_diff_density_min         -0.465
_refine_diff_density_rms         0.059
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_om986m
_audit_block_doi                 10.5517/ccdc.csd.cc1n5d6f
_database_code_depnum_ccdc_archive 'CCDC 1524524'
_audit_update_record             
;
2016-12-26 deposited with the CCDC.
2017-07-05 downloaded from the CCDC.
;


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C56 H48 Cl2 N4 O4 Pd Se2, 2(C2 H3 N)'
_chemical_formula_sum            'C60 H54 Cl2 N6 O4 Pd Se2'
_chemical_formula_weight         1258.31

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Se Se -0.0929 2.2259 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Pd Pd -0.9988 1.0072 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

_cell_length_a                   9.430(2)
_cell_length_b                   10.752(3)
_cell_length_c                   14.940(4)
_cell_angle_alpha                81.965(4)
_cell_angle_beta                 89.092(5)
_cell_angle_gamma                68.046(4)
_cell_volume                     1390.1(6)
_cell_formula_units_Z            1
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    2277
_cell_measurement_theta_min      2.31
_cell_measurement_theta_max      25.60

_exptl_crystal_description       block
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.29
_exptl_crystal_density_meas      1.503
_exptl_crystal_density_diffrn    1.503
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             636.0
_exptl_absorpt_coefficient_mu    1.792
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.556
_exptl_absorpt_correction_T_max  0.598
_exptl_absorpt_process_details   '(SADABS; Bruker, 2000)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5997
_diffrn_reflns_av_R_equivalents  0.0202
_diffrn_reflns_av_sigmaI/netI    0.0531
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.31
_diffrn_reflns_theta_max         25.00
_reflns_number_total             4899
_reflns_number_gt                3573
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1157P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4504
_refine_ls_number_parameters     341
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0590
_refine_ls_R_factor_gt           0.0447
_refine_ls_wR_factor_ref         0.1651
_refine_ls_wR_factor_gt          0.1382
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_restrained_S_all      1.023
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.7980(7) 0.1553(7) 0.5834(4) 0.0522(16) Uani 1 1 d . . .
H1 H 0.7419 0.2407 0.5522 0.063 Uiso 1 1 calc R . .
C2 C 0.9569(9) 0.1087(10) 0.5914(6) 0.079(2) Uani 1 1 d . . .
H2 H 1.0074 0.1614 0.5621 0.094 Uiso 1 1 calc R . .
C3 C 1.0385(9) -0.0111(10) 0.6407(6) 0.075(2) Uani 1 1 d . . .
H3 H 1.1445 -0.0408 0.6458 0.090 Uiso 1 1 calc R . .
C4 C 0.9628(9) -0.0906(10) 0.6840(7) 0.098(3) Uani 1 1 d . . .
H4 H 1.0189 -0.1721 0.7198 0.118 Uiso 1 1 calc R . .
C5 C 0.8063(7) -0.0502(6) 0.6748(4) 0.0513(16) Uani 1 1 d . . .
H5 H 0.7559 -0.1039 0.7028 0.062 Uiso 1 1 calc R . .
C6 C 0.7259(6) 0.0734(6) 0.6221(4) 0.0413(14) Uani 1 1 d . . .
C7 C 0.4834(6) 0.1233(5) 0.6977(4) 0.0340(12) Uani 1 1 d . . .
C8 C 0.4049(7) 0.0358(6) 0.7242(4) 0.0468(15) Uani 1 1 d . . .
H8 H 0.4061 -0.0286 0.6883 0.056 Uiso 1 1 calc R . .
C9 C 0.3282(8) 0.0456(7) 0.8017(5) 0.0599(18) Uani 1 1 d . . .
H9 H 0.2761 -0.0117 0.8186 0.072 Uiso 1 1 calc R . .
C10 C 0.3266(9) 0.1382(8) 0.8549(5) 0.066(2) Uani 1 1 d . . .
H10 H 0.2726 0.1451 0.9078 0.079 Uiso 1 1 calc R . .
C11 C 0.4072(9) 0.2247(8) 0.8298(5) 0.071(2) Uani 1 1 d . . .
H11 H 0.4075 0.2874 0.8667 0.085 Uiso 1 1 calc R . .
C12 C 0.4845(7) 0.2158(6) 0.7514(4) 0.0454(14) Uani 1 1 d . . .
H12 H 0.5375 0.2725 0.7347 0.055 Uiso 1 1 calc R . .
C13 C 0.4927(6) 0.1435(5) 0.5321(4) 0.0334(12) Uani 1 1 d . . .
C14 C 0.3217(6) 0.2060(5) 0.5243(4) 0.0359(12) Uani 1 1 d . . .
H14A H 0.2787 0.2003 0.5835 0.043 Uiso 1 1 calc R . .
H14B H 0.2823 0.1596 0.4859 0.043 Uiso 1 1 calc R . .
C15 C 0.2836(6) 0.3680(5) 0.3430(4) 0.0351(12) Uani 1 1 d . . .
H15A H 0.3770 0.2925 0.3346 0.042 Uiso 1 1 calc R . .
H15B H 0.1972 0.3485 0.3240 0.042 Uiso 1 1 calc R . .
C16 C 0.2842(6) 0.4925(5) 0.2904(4) 0.0333(12) Uani 1 1 d . . .
C17 C 0.2248(7) 0.6403(5) 0.1480(4) 0.0398(13) Uani 1 1 d . . .
C18 C 0.1350(8) 0.7633(6) 0.1730(5) 0.0569(17) Uani 1 1 d . . .
H18 H 0.0789 0.7679 0.2250 0.068 Uiso 1 1 calc R . .
C19 C 0.1305(10) 0.8847(7) 0.1162(6) 0.070(2) Uani 1 1 d . . .
H19 H 0.0757 0.9694 0.1329 0.084 Uiso 1 1 calc R . .
C20 C 0.2027(10) 0.8751(8) 0.0424(6) 0.076(2) Uani 1 1 d . . .
H20 H 0.1937 0.9543 0.0046 0.091 Uiso 1 1 calc R . .
C21 C 0.2919(10) 0.7540(9) 0.0166(5) 0.072(2) Uani 1 1 d . . .
H21 H 0.3427 0.7529 -0.0374 0.086 Uiso 1 1 calc R . .
C22 C 0.3071(8) 0.6387(7) 0.0670(4) 0.0535(16) Uani 1 1 d . . .
H22 H 0.3710 0.5568 0.0499 0.064 Uiso 1 1 calc R . .
C23 C 0.1833(7) 0.4281(5) 0.1606(4) 0.0382(13) Uani 1 1 d . . .
C24 C 0.0335(8) 0.4687(7) 0.1374(4) 0.0537(16) Uani 1 1 d . . .
H24 H -0.0352 0.5521 0.1496 0.064 Uiso 1 1 calc R . .
C25 C -0.0175(10) 0.3854(9) 0.0951(5) 0.068(2) Uani 1 1 d . . .
H25 H -0.1207 0.4123 0.0792 0.082 Uiso 1 1 calc R . .
C26 C 0.0847(12) 0.2637(8) 0.0770(6) 0.081(3) Uani 1 1 d . . .
H26 H 0.0510 0.2090 0.0470 0.097 Uiso 1 1 calc R . .
C27 C 0.2329(10) 0.2220(7) 0.1018(5) 0.072(2) Uani 1 1 d . . .
H27 H 0.3003 0.1368 0.0920 0.086 Uiso 1 1 calc R . .
C28 C 0.2858(8) 0.3056(6) 0.1421(4) 0.0506(15) Uani 1 1 d . . .
H28 H 0.3895 0.2792 0.1564 0.061 Uiso 1 1 calc R . .
C29 C 0.6587(9) 0.3533(10) 0.2689(7) 0.088(3) Uani 1 1 d . . .
C30 C 0.6925(11) 0.3925(12) 0.3515(8) 0.119(4) Uani 1 1 d . . .
H30A H 0.6013 0.4584 0.3711 0.178 Uiso 1 1 calc R . .
H30B H 0.7693 0.4310 0.3414 0.178 Uiso 1 1 calc R . .
H30C H 0.7295 0.3144 0.3971 0.178 Uiso 1 1 calc R . .
Cl1 Cl 0.06370(17) 0.41586(17) 0.64839(10) 0.0538(4) Uani 1 1 d . . .
N1 N 0.5621(5) 0.1163(4) 0.6156(3) 0.0345(10) Uani 1 1 d . . .
N2 N 0.2369(5) 0.5178(4) 0.2016(3) 0.0378(11) Uani 1 1 d . . .
N3 N 0.6348(10) 0.3154(13) 0.2095(7) 0.161(5) Uani 1 1 d . . .
O1 O 0.5653(4) 0.1231(4) 0.4626(3) 0.0463(10) Uani 1 1 d . . .
O2 O 0.3312(5) 0.5692(4) 0.3221(3) 0.0450(10) Uani 1 1 d . . .
Pd1 Pd 0.0000 0.5000 0.5000 0.0316(2) Uani 1 2 d S . .
Se1 Se 0.26854(5) 0.39534(5) 0.47131(3) 0.0320(2) 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 C6 1.366(8) . ?
C1 C2 1.392(10) . ?
C1 H1 0.9300 . ?
C2 C3 1.343(12) . ?
C2 H2 0.9300 . ?
C3 C4 1.396(12) . ?
C3 H3 0.9300 . ?
C4 C5 1.377(10) . ?
C4 H4 0.9300 . ?
C5 C6 1.390(9) . ?
C5 H5 0.9300 . ?
C6 N1 1.438(7) . ?
C7 C12 1.365(7) . ?
C7 C8 1.413(8) . ?
C7 N1 1.420(7) . ?
C8 C9 1.350(8) . ?
C8 H8 0.9300 . ?
C9 C10 1.354(10) . ?
C9 H9 0.9300 . ?
C10 C11 1.415(10) . ?
C10 H10 0.9300 . ?
C11 C12 1.365(9) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C13 O1 1.234(6) . ?
C13 N1 1.361(7) . ?
C13 C14 1.497(7) . ?
C14 Se1 1.955(5) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 C16 1.456(7) . ?
C15 Se1 1.974(5) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 O2 1.222(6) . ?
C16 N2 1.363(7) . ?
C17 C18 1.377(8) . ?
C17 N2 1.408(7) . ?
C17 C22 1.426(8) . ?
C18 C19 1.441(9) . ?
C18 H18 0.9300 . ?
C19 C20 1.283(10) . ?
C19 H19 0.9300 . ?
C20 C21 1.364(11) . ?
C20 H20 0.9300 . ?
C21 C22 1.318(9) . ?
C21 H21 0.9300 . ?
C22 H22 0.9300 . ?
C23 C24 1.348(8) . ?
C23 C28 1.374(8) . ?
C23 N2 1.449(7) . ?
C24 C25 1.387(9) . ?
C24 H24 0.9300 . ?
C25 C26 1.364(11) . ?
C25 H25 0.9300 . ?
C26 C27 1.339(11) . ?
C26 H26 0.9300 . ?
C27 C28 1.384(9) . ?
C27 H27 0.9300 . ?
C28 H28 0.9300 . ?
C29 N3 1.086(11) . ?
C29 C30 1.435(13) . ?
C30 H30A 0.9600 . ?
C30 H30B 0.9600 . ?
C30 H30C 0.9600 . ?
Cl1 Pd1 2.2736(16) . ?
Pd1 Cl1 2.2736(16) 2_566 ?
Pd1 Se1 2.4151(7) . ?
Pd1 Se1 2.4151(7) 2_566 ?

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 118.8(7) . . ?
C6 C1 H1 120.6 . . ?
C2 C1 H1 120.6 . . ?
C3 C2 C1 121.1(8) . . ?
C3 C2 H2 119.4 . . ?
C1 C2 H2 119.4 . . ?
C2 C3 C4 119.5(7) . . ?
C2 C3 H3 120.3 . . ?
C4 C3 H3 120.3 . . ?
C5 C4 C3 121.0(8) . . ?
C5 C4 H4 119.5 . . ?
C3 C4 H4 119.5 . . ?
C4 C5 C6 117.8(7) . . ?
C4 C5 H5 121.1 . . ?
C6 C5 H5 121.1 . . ?
C1 C6 C5 121.5(6) . . ?
C1 C6 N1 121.2(5) . . ?
C5 C6 N1 117.2(5) . . ?
C12 C7 C8 120.0(5) . . ?
C12 C7 N1 119.2(5) . . ?
C8 C7 N1 120.8(5) . . ?
C9 C8 C7 120.0(6) . . ?
C9 C8 H8 120.0 . . ?
C7 C8 H8 120.0 . . ?
C8 C9 C10 120.6(6) . . ?
C8 C9 H9 119.7 . . ?
C10 C9 H9 119.7 . . ?
C9 C10 C11 119.8(6) . . ?
C9 C10 H10 120.1 . . ?
C11 C10 H10 120.1 . . ?
C12 C11 C10 120.0(6) . . ?
C12 C11 H11 120.0 . . ?
C10 C11 H11 120.0 . . ?
C11 C12 C7 119.6(6) . . ?
C11 C12 H12 120.2 . . ?
C7 C12 H12 120.2 . . ?
O1 C13 N1 122.6(5) . . ?
O1 C13 C14 119.0(5) . . ?
N1 C13 C14 118.4(5) . . ?
C13 C14 Se1 106.5(3) . . ?
C13 C14 H14A 110.4 . . ?
Se1 C14 H14A 110.4 . . ?
C13 C14 H14B 110.4 . . ?
Se1 C14 H14B 110.4 . . ?
H14A C14 H14B 108.6 . . ?
C16 C15 Se1 107.4(3) . . ?
C16 C15 H15A 110.2 . . ?
Se1 C15 H15A 110.2 . . ?
C16 C15 H15B 110.2 . . ?
Se1 C15 H15B 110.2 . . ?
H15A C15 H15B 108.5 . . ?
O2 C16 N2 120.4(5) . . ?
O2 C16 C15 122.3(5) . . ?
N2 C16 C15 117.3(4) . . ?
C18 C17 N2 121.0(5) . . ?
C18 C17 C22 118.8(6) . . ?
N2 C17 C22 120.2(5) . . ?
C17 C18 C19 118.1(6) . . ?
C17 C18 H18 120.9 . . ?
C19 C18 H18 120.9 . . ?
C20 C19 C18 119.4(7) . . ?
C20 C19 H19 120.3 . . ?
C18 C19 H19 120.3 . . ?
C19 C20 C21 123.1(7) . . ?
C19 C20 H20 118.4 . . ?
C21 C20 H20 118.4 . . ?
C22 C21 C20 120.9(7) . . ?
C22 C21 H21 119.5 . . ?
C20 C21 H21 119.5 . . ?
C21 C22 C17 119.5(7) . . ?
C21 C22 H22 120.2 . . ?
C17 C22 H22 120.2 . . ?
C24 C23 C28 120.6(5) . . ?
C24 C23 N2 119.4(5) . . ?
C28 C23 N2 119.9(5) . . ?
C23 C24 C25 119.6(7) . . ?
C23 C24 H24 120.2 . . ?
C25 C24 H24 120.2 . . ?
C26 C25 C24 119.6(7) . . ?
C26 C25 H25 120.2 . . ?
C24 C25 H25 120.2 . . ?
C27 C26 C25 120.9(7) . . ?
C27 C26 H26 119.6 . . ?
C25 C26 H26 119.6 . . ?
C26 C27 C28 120.1(7) . . ?
C26 C27 H27 120.0 . . ?
C28 C27 H27 120.0 . . ?
C23 C28 C27 119.2(7) . . ?
C23 C28 H28 120.4 . . ?
C27 C28 H28 120.4 . . ?
N3 C29 C30 175.3(14) . . ?
C29 C30 H30A 109.5 . . ?
C29 C30 H30B 109.5 . . ?
H30A C30 H30B 109.5 . . ?
C29 C30 H30C 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
C13 N1 C7 124.1(4) . . ?
C13 N1 C6 118.5(5) . . ?
C7 N1 C6 117.4(4) . . ?
C16 N2 C17 120.5(4) . . ?
C16 N2 C23 122.2(4) . . ?
C17 N2 C23 117.0(4) . . ?
Cl1 Pd1 Cl1 180.00(3) . 2_566 ?
Cl1 Pd1 Se1 87.18(4) . . ?
Cl1 Pd1 Se1 92.82(4) 2_566 . ?
Cl1 Pd1 Se1 92.82(4) . 2_566 ?
Cl1 Pd1 Se1 87.18(4) 2_566 2_566 ?
Se1 Pd1 Se1 180.0 . 2_566 ?
C14 Se1 C15 97.6(2) . . ?
C14 Se1 Pd1 103.57(15) . . ?
C15 Se1 Pd1 107.27(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
C6 C1 C2 C3 -3.9(12) . . . . ?
C1 C2 C3 C4 0.5(13) . . . . ?
C2 C3 C4 C5 2.1(13) . . . . ?
C3 C4 C5 C6 -1.1(12) . . . . ?
C2 C1 C6 C5 4.9(10) . . . . ?
C2 C1 C6 N1 -179.7(6) . . . . ?
C4 C5 C6 C1 -2.4(10) . . . . ?
C4 C5 C6 N1 -178.0(6) . . . . ?
C12 C7 C8 C9 1.4(9) . . . . ?
N1 C7 C8 C9 -178.7(6) . . . . ?
C7 C8 C9 C10 -0.5(11) . . . . ?
C8 C9 C10 C11 -0.7(12) . . . . ?
C9 C10 C11 C12 1.0(12) . . . . ?
C10 C11 C12 C7 0.0(11) . . . . ?
C8 C7 C12 C11 -1.2(9) . . . . ?
N1 C7 C12 C11 179.0(6) . . . . ?
O1 C13 C14 Se1 -71.1(5) . . . . ?
N1 C13 C14 Se1 106.3(4) . . . . ?
Se1 C15 C16 O2 27.3(6) . . . . ?
Se1 C15 C16 N2 -156.0(4) . . . . ?
N2 C17 C18 C19 178.6(6) . . . . ?
C22 C17 C18 C19 -0.8(9) . . . . ?
C17 C18 C19 C20 3.7(11) . . . . ?
C18 C19 C20 C21 -3.8(13) . . . . ?
C19 C20 C21 C22 0.8(13) . . . . ?
C20 C21 C22 C17 2.3(11) . . . . ?
C18 C17 C22 C21 -2.2(9) . . . . ?
N2 C17 C22 C21 178.5(6) . . . . ?
C28 C23 C24 C25 0.6(9) . . . . ?
N2 C23 C24 C25 177.6(6) . . . . ?
C23 C24 C25 C26 -0.4(11) . . . . ?
C24 C25 C26 C27 1.9(13) . . . . ?
C25 C26 C27 C28 -3.5(13) . . . . ?
C24 C23 C28 C27 -2.1(9) . . . . ?
N2 C23 C28 C27 -179.1(6) . . . . ?
C26 C27 C28 C23 3.5(11) . . . . ?
O1 C13 N1 C7 -172.3(5) . . . . ?
C14 C13 N1 C7 10.3(7) . . . . ?
O1 C13 N1 C6 5.6(7) . . . . ?
C14 C13 N1 C6 -171.7(4) . . . . ?
C12 C7 N1 C13 -116.5(6) . . . . ?
C8 C7 N1 C13 63.7(7) . . . . ?
C12 C7 N1 C6 65.5(7) . . . . ?
C8 C7 N1 C6 -114.3(6) . . . . ?
C1 C6 N1 C13 61.5(7) . . . . ?
C5 C6 N1 C13 -123.0(6) . . . . ?
C1 C6 N1 C7 -120.4(6) . . . . ?
C5 C6 N1 C7 55.1(7) . . . . ?
O2 C16 N2 C17 -7.5(8) . . . . ?
C15 C16 N2 C17 175.8(5) . . . . ?
O2 C16 N2 C23 178.7(5) . . . . ?
C15 C16 N2 C23 2.0(7) . . . . ?
C18 C17 N2 C16 -56.3(7) . . . . ?
C22 C17 N2 C16 123.1(6) . . . . ?
C18 C17 N2 C23 117.9(6) . . . . ?
C22 C17 N2 C23 -62.8(7) . . . . ?
C24 C23 N2 C16 109.3(6) . . . . ?
C28 C23 N2 C16 -73.6(7) . . . . ?
C24 C23 N2 C17 -64.7(7) . . . . ?
C28 C23 N2 C17 112.3(6) . . . . ?
C13 C14 Se1 C15 85.3(4) . . . . ?
C13 C14 Se1 Pd1 -164.8(3) . . . . ?
C16 C15 Se1 C14 -166.6(4) . . . . ?
C16 C15 Se1 Pd1 86.6(4) . . . . ?
Cl1 Pd1 Se1 C14 54.35(19) . . . . ?
Cl1 Pd1 Se1 C14 -125.65(19) 2_566 . . . ?
Se1 Pd1 Se1 C14 137(100) 2_566 . . . ?
Cl1 Pd1 Se1 C15 156.95(16) . . . . ?
Cl1 Pd1 Se1 C15 -23.05(16) 2_566 . . . ?
Se1 Pd1 Se1 C15 -120(100) 2_566 . . . ?

_diffrn_measured_fraction_theta_max 0.989
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.989
_refine_diff_density_max         0.625
_refine_diff_density_min         -0.568
_refine_diff_density_rms         0.136
####################################################################### 
# 
# 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_sn812m
_audit_block_doi                 10.5517/ccdc.csd.cc1n5d5d
_database_code_depnum_ccdc_archive 'CCDC 1524523'
_audit_update_record             
;
2016-12-26 deposited with the CCDC.
2017-07-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C56 H48 Cl2 N4 O4 Pd S2, 2(C H Cl3)'
_chemical_formula_sum            'C58 H50 Cl8 N4 O4 Pd S2'
_chemical_formula_weight         1321.14

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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Pd Pd -0.9988 1.0072 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

_cell_length_a                   11.700(4)
_cell_length_b                   12.284(4)
_cell_length_c                   12.639(4)
_cell_angle_alpha                96.477(7)
_cell_angle_beta                 114.035(6)
_cell_angle_gamma                106.735(6)
_cell_volume                     1532.8(9)
_cell_formula_units_Z            1
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    4380
_cell_measurement_theta_min      2.28
_cell_measurement_theta_max      20.42

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.27
_exptl_crystal_density_meas      1.431
_exptl_crystal_density_diffrn    1.431
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             672
_exptl_absorpt_coefficient_mu    0.767
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.791
_exptl_absorpt_correction_T_max  0.810
_exptl_absorpt_process_details   '(SADABS; Bruker, 2000)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            14795
_diffrn_reflns_av_R_equivalents  0.0452
_diffrn_reflns_av_sigmaI/netI    0.0583
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.05
_diffrn_reflns_theta_max         25.00
_reflns_number_total             5395
_reflns_number_gt                4590
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0755P)²+2.5403P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5395
_refine_ls_number_parameters     349
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0771
_refine_ls_R_factor_gt           0.0655
_refine_ls_wR_factor_ref         0.1689
_refine_ls_wR_factor_gt          0.1624
_refine_ls_goodness_of_fit_ref   1.108
_refine_ls_restrained_S_all      1.108
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Pd1 Pd 0.5000 0.0000 0.5000 0.0355(2) Uani 1 2 d S . .
S1 S 0.45320(12) 0.13509(11) 0.39033(12) 0.0421(3) Uani 1 1 d . . .
Cl1 Cl 0.71934(13) 0.09910(13) 0.54543(15) 0.0599(4) Uani 1 1 d . . .
O2 O 0.4291(4) 0.3828(3) 0.3722(4) 0.0561(10) Uani 1 1 d . . .
N2 N 0.6571(4) 0.4431(3) 0.4589(4) 0.0429(10) Uani 1 1 d . . .
O1 O 0.2426(4) -0.0340(4) 0.1768(4) 0.0573(10) Uani 1 1 d . . .
N1 N 0.0580(4) -0.0233(4) 0.1907(4) 0.0435(10) Uani 1 1 d . . .
C15 C 0.5289(5) 0.2753(4) 0.5043(5) 0.0470(12) Uani 1 1 d . . .
H15A H 0.4758 0.2765 0.5463 0.056 Uiso 1 1 calc R . .
H15B H 0.6193 0.2859 0.5624 0.056 Uiso 1 1 calc R . .
C16 C 0.5329(5) 0.3733(4) 0.4405(5) 0.0428(12) Uani 1 1 d . . .
Cl2 Cl 0.5247(4) 0.8926(4) 0.2188(4) 0.222(2) Uani 1 1 d . . .
C6 C 0.0013(5) 0.0398(5) 0.2457(5) 0.0456(12) Uani 1 1 d . . .
C23 C 0.7809(5) 0.4493(4) 0.5554(5) 0.0440(12) Uani 1 1 d . . .
C14 C 0.2775(5) 0.1183(4) 0.3346(5) 0.0444(12) Uani 1 1 d . . .
H14A H 0.2503 0.1072 0.3969 0.053 Uiso 1 1 calc R . .
H14B H 0.2652 0.1885 0.3120 0.053 Uiso 1 1 calc R . .
C7 C -0.0361(5) -0.1305(5) 0.0981(4) 0.0461(12) Uani 1 1 d . . .
C13 C 0.1923(5) 0.0121(4) 0.2265(5) 0.0453(12) Uani 1 1 d . . .
C17 C 0.6663(5) 0.5220(5) 0.3842(5) 0.0483(13) Uani 1 1 d . . .
C24 C 0.8135(6) 0.4961(5) 0.6726(6) 0.0598(15) Uani 1 1 d . . .
H24 H 0.7557 0.5240 0.6905 0.072 Uiso 1 1 calc R . .
C5 C -0.0458(6) -0.0070(5) 0.3198(5) 0.0566(14) Uani 1 1 d . . .
H5 H -0.0360 -0.0763 0.3373 0.068 Uiso 1 1 calc R . .
C8 C -0.0105(7) -0.2334(5) 0.0991(6) 0.0632(16) Uani 1 1 d . . .
H8 H 0.0697 -0.2343 0.1570 0.076 Uiso 1 1 calc R . .
C28 C 0.8670(6) 0.4115(5) 0.5281(6) 0.0612(15) Uani 1 1 d . . .
H28 H 0.8453 0.3818 0.4485 0.073 Uiso 1 1 calc R . .
C12 C -0.1561(6) -0.1307(5) 0.0128(5) 0.0580(15) Uani 1 1 d . . .
H12 H -0.1732 -0.0613 0.0125 0.070 Uiso 1 1 calc R . .
C10 C -0.2272(7) -0.3360(6) -0.0734(6) 0.075(2) Uani 1 1 d . . .
H10 H -0.2916 -0.4049 -0.1314 0.090 Uiso 1 1 calc R . .
C18 C 0.7308(6) 0.6416(5) 0.4352(7) 0.0632(16) Uani 1 1 d . . .
H18 H 0.7638 0.6712 0.5172 0.076 Uiso 1 1 calc R . .
C22 C 0.6184(7) 0.4796(7) 0.2643(6) 0.0741(19) Uani 1 1 d . . .
H22 H 0.5741 0.3990 0.2290 0.089 Uiso 1 1 calc R . .
C9 C -0.1078(8) -0.3358(6) 0.0114(6) 0.077(2) Uani 1 1 d . . .
H9 H -0.0914 -0.4055 0.0103 0.092 Uiso 1 1 calc R . .
C1 C -0.0097(6) 0.1437(5) 0.2211(6) 0.0632(16) Uani 1 1 d . . .
H1 H 0.0225 0.1764 0.1712 0.076 Uiso 1 1 calc R . .
C26 C 1.0205(6) 0.4637(7) 0.7372(7) 0.077(2) Uani 1 1 d . . .
H26 H 1.1021 0.4695 0.7987 0.093 Uiso 1 1 calc R . .
C11 C -0.2496(7) -0.2323(7) -0.0708(6) 0.075(2) Uani 1 1 d . . .
H11 H -0.3305 -0.2316 -0.1276 0.091 Uiso 1 1 calc R . .
C27 C 0.9880(7) 0.4181(7) 0.6213(8) 0.077(2) Uani 1 1 d . . .
H27 H 1.0465 0.3912 0.6038 0.093 Uiso 1 1 calc R . .
C4 C -0.1066(7) 0.0466(6) 0.3681(7) 0.0740(19) Uani 1 1 d . . .
H4 H -0.1395 0.0133 0.4174 0.089 Uiso 1 1 calc R . .
C19 C 0.7470(8) 0.7172(7) 0.3664(9) 0.084(2) Uani 1 1 d . . .
H19 H 0.7914 0.7978 0.4016 0.101 Uiso 1 1 calc R . .
C3 C -0.1194(7) 0.1485(7) 0.3444(8) 0.083(2) Uani 1 1 d . . .
H3 H -0.1618 0.1846 0.3770 0.100 Uiso 1 1 calc R . .
C25 C 0.9334(7) 0.5011(7) 0.7636(6) 0.079(2) Uani 1 1 d . . .
H25 H 0.9550 0.5302 0.8433 0.095 Uiso 1 1 calc R . .
C2 C -0.0704(8) 0.1986(6) 0.2730(8) 0.087(2) Uani 1 1 d . . .
H2 H -0.0775 0.2696 0.2589 0.105 Uiso 1 1 calc R . .
Cl4 Cl 0.3168(7) 0.6858(5) 0.1381(8) 0.299(4) Uani 1 1 d . . .
C20 C 0.6976(8) 0.6736(8) 0.2459(9) 0.091(3) Uani 1 1 d . . .
H20 H 0.7067 0.7251 0.1987 0.109 Uiso 1 1 calc R . .
C21 C 0.6353(8) 0.5559(10) 0.1942(7) 0.099(3) Uani 1 1 d . . .
H21 H 0.6041 0.5266 0.1124 0.118 Uiso 1 1 calc R . .
Cl3 Cl 0.3837(9) 0.7689(9) -0.0224(5) 0.382(6) Uani 1 1 d . . .
C36 C 0.3767(10) 0.8133(9) 0.1012(10) 0.124(4) Uani 1 1 d . . .
H36 H 0.3150 0.8559 0.0870 0.148 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 2.2892(15) 2_656 ?
Pd1 Cl1 2.2892(15) . ?
Pd1 S1 2.3235(14) . ?
Pd1 S1 2.3235(14) 2_656 ?
S1 C14 1.819(5) . ?
S1 C15 1.830(5) . ?
O2 C16 1.218(6) . ?
N2 C16 1.365(6) . ?
N2 C23 1.438(6) . ?
N2 C17 1.439(7) . ?
O1 C13 1.213(6) . ?
N1 C13 1.359(7) . ?
N1 C6 1.441(7) . ?
N1 C7 1.443(6) . ?
C15 C16 1.523(7) . ?
Cl2 C36 1.662(10) . ?
C6 C5 1.367(8) . ?
C6 C1 1.376(8) . ?
C23 C28 1.366(8) . ?
C23 C24 1.376(8) . ?
C14 C13 1.517(7) . ?
C7 C12 1.378(8) . ?
C7 C8 1.380(8) . ?
C17 C22 1.357(9) . ?
C17 C18 1.377(8) . ?
C24 C25 1.384(9) . ?
C5 C4 1.359(9) . ?
C8 C9 1.393(8) . ?
C28 C27 1.397(9) . ?
C12 C11 1.359(9) . ?
C10 C9 1.370(10) . ?
C10 C11 1.372(10) . ?
C18 C19 1.367(9) . ?
C22 C21 1.389(10) . ?
C1 C2 1.394(9) . ?
C26 C27 1.357(10) . ?
C26 C25 1.369(10) . ?
C4 C3 1.354(10) . ?
C19 C20 1.365(12) . ?
C3 C2 1.366(11) . ?
Cl4 C36 1.722(13) . ?
C20 C21 1.357(12) . ?
Cl3 C36 1.638(11) . ?

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
Cl1 Pd1 Cl1 180.000(1) 2_656 . ?
Cl1 Pd1 S1 94.79(5) 2_656 . ?
Cl1 Pd1 S1 85.21(5) . . ?
Cl1 Pd1 S1 85.21(5) 2_656 2_656 ?
Cl1 Pd1 S1 94.79(5) . 2_656 ?
S1 Pd1 S1 180.00(6) . 2_656 ?
C14 S1 C15 98.4(2) . . ?
C14 S1 Pd1 110.65(18) . . ?
C15 S1 Pd1 104.24(18) . . ?
C16 N2 C23 123.6(4) . . ?
C16 N2 C17 118.9(4) . . ?
C23 N2 C17 117.3(4) . . ?
C13 N1 C6 122.6(4) . . ?
C13 N1 C7 121.4(4) . . ?
C6 N1 C7 115.9(4) . . ?
C16 C15 S1 107.7(4) . . ?
O2 C16 N2 123.1(5) . . ?
O2 C16 C15 120.6(4) . . ?
N2 C16 C15 116.2(4) . . ?
C5 C6 C1 120.3(5) . . ?
C5 C6 N1 119.0(5) . . ?
C1 C6 N1 120.6(5) . . ?
C28 C23 C24 120.9(5) . . ?
C28 C23 N2 118.7(5) . . ?
C24 C23 N2 120.4(5) . . ?
C13 C14 S1 108.6(4) . . ?
C12 C7 C8 120.2(5) . . ?
C12 C7 N1 119.0(5) . . ?
C8 C7 N1 120.6(5) . . ?
O1 C13 N1 124.3(5) . . ?
O1 C13 C14 121.5(5) . . ?
N1 C13 C14 114.2(5) . . ?
C22 C17 C18 119.2(6) . . ?
C22 C17 N2 120.7(5) . . ?
C18 C17 N2 119.9(5) . . ?
C23 C24 C25 119.1(6) . . ?
C4 C5 C6 120.8(6) . . ?
C7 C8 C9 118.4(6) . . ?
C23 C28 C27 119.1(6) . . ?
C11 C12 C7 120.0(6) . . ?
C9 C10 C11 118.6(6) . . ?
C19 C18 C17 120.7(7) . . ?
C17 C22 C21 120.3(7) . . ?
C10 C9 C8 121.4(7) . . ?
C6 C1 C2 118.2(6) . . ?
C27 C26 C25 120.1(6) . . ?
C12 C11 C10 121.4(6) . . ?
C26 C27 C28 120.4(6) . . ?
C3 C4 C5 119.9(7) . . ?
C20 C19 C18 119.6(7) . . ?
C4 C3 C2 120.5(7) . . ?
C26 C25 C24 120.4(7) . . ?
C3 C2 C1 120.3(6) . . ?
C21 C20 C19 120.6(7) . . ?
C20 C21 C22 119.5(8) . . ?
Cl3 C36 Cl2 114.9(7) . . ?
Cl3 C36 Cl4 104.7(7) . . ?
Cl2 C36 Cl4 105.4(7) . . ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.747
_refine_diff_density_min         -0.711
_refine_diff_density_rms         0.091
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_mp865m
_audit_block_doi                 10.5517/ccdc.csd.cc1n5d3b
_database_code_depnum_ccdc_archive 'CCDC 1524521'
_audit_update_record             
;
2016-12-26 deposited with the CCDC.
2017-07-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C28 H24 N2 O2 S'
_chemical_formula_sum            'C28 H24 N2 O2 S'
_chemical_formula_weight         452.55

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   C2
_symmetry_space_group_name_Hall  'C 2y'

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

_cell_length_a                   17.766(7)
_cell_length_b                   5.557(2)
_cell_length_c                   13.792(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 120.633(8)
_cell_angle_gamma                90.00
_cell_volume                     1171.5(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    510
_cell_measurement_theta_min      2.32
_cell_measurement_theta_max      14.81

_exptl_crystal_description       block
_exptl_crystal_colour            white
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.28
_exptl_crystal_density_meas      1.283
_exptl_crystal_density_diffrn    1.283
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             476
_exptl_absorpt_coefficient_mu    0.166
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.946
_exptl_absorpt_correction_T_max  0.958
_exptl_absorpt_process_details   '(SADABS; Bruker, 2000)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5687
_diffrn_reflns_av_R_equivalents  0.0717
_diffrn_reflns_av_sigmaI/netI    0.1002
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.66
_diffrn_reflns_theta_max         24.95
_reflns_number_total             2058
_reflns_number_gt                1406
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0269P)²+0.7341P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.20(19)
_refine_ls_number_reflns         2058
_refine_ls_number_parameters     150
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1168
_refine_ls_R_factor_gt           0.0804
_refine_ls_wR_factor_ref         0.1283
_refine_ls_wR_factor_gt          0.1166
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_restrained_S_all      1.082
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.5000 0.5733(3) 0.5000 0.0542(6) Uani 1 2 d S . .
N1 N 0.4935(2) 0.1364(6) 0.2640(3) 0.0450(11) Uani 1 1 d . . .
C13 C 0.4669(3) 0.2384(10) 0.3323(4) 0.0480(13) Uani 1 1 d . . .
O1 O 0.3927(2) 0.2154(7) 0.3145(2) 0.0609(11) Uani 1 1 d . . .
C1 C 0.6033(4) 0.3597(10) 0.2449(4) 0.0625(16) Uani 1 1 d . . .
H1 H 0.5612 0.4743 0.2019 0.075 Uiso 1 1 calc R . .
C7 C 0.4378(3) -0.0237(9) 0.1735(4) 0.0484(14) Uani 1 1 d . . .
C14 C 0.5376(3) 0.3718(10) 0.4333(4) 0.0568(15) Uani 1 1 d . . .
H14A H 0.5722 0.4623 0.4097 0.068 Uiso 1 1 calc R . .
H14B H 0.5759 0.2545 0.4886 0.068 Uiso 1 1 calc R . .
C2 C 0.5817(3) 0.1666(9) 0.2852(4) 0.0470(13) Uani 1 1 d . . .
C8 C 0.4262(3) 0.0122(11) 0.0683(4) 0.0678(17) Uani 1 1 d . . .
H8 H 0.4530 0.1418 0.0553 0.081 Uiso 1 1 calc R . .
C12 C 0.3966(3) -0.2152(9) 0.1908(4) 0.0543(14) Uani 1 1 d . . .
H12 H 0.4038 -0.2411 0.2617 0.065 Uiso 1 1 calc R . .
C3 C 0.6424(4) -0.0042(11) 0.3462(5) 0.0791(19) Uani 1 1 d . . .
H3 H 0.6272 -0.1370 0.3736 0.095 Uiso 1 1 calc R . .
C11 C 0.3451(3) -0.3677(10) 0.1034(5) 0.0672(17) Uani 1 1 d . . .
H11 H 0.3172 -0.4963 0.1153 0.081 Uiso 1 1 calc R . .
C6 C 0.6883(4) 0.3865(15) 0.2676(5) 0.088(2) Uani 1 1 d . . .
H6 H 0.7035 0.5212 0.2414 0.105 Uiso 1 1 calc R . .
C10 C 0.3344(4) -0.3317(13) -0.0009(5) 0.083(2) Uani 1 1 d . . .
H10 H 0.2995 -0.4357 -0.0599 0.100 Uiso 1 1 calc R . .
C9 C 0.3747(5) -0.1447(13) -0.0181(5) 0.088(2) Uani 1 1 d . . .
H9 H 0.3677 -0.1213 -0.0890 0.106 Uiso 1 1 calc R . .
C4 C 0.7261(4) 0.0200(16) 0.3671(6) 0.106(3) Uani 1 1 d . . .
H4 H 0.7675 -0.0979 0.4081 0.128 Uiso 1 1 calc R . .
C5 C 0.7495(4) 0.217(2) 0.3283(6) 0.105(3) Uani 1 1 d . . .
H5 H 0.8065 0.2335 0.3432 0.126 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
S1 C14 1.781(5) . ?
S1 C14 1.781(5) 2_656 ?
N1 C13 1.374(5) . ?
N1 C7 1.438(5) . ?
N1 C2 1.449(5) . ?
C13 O1 1.220(5) . ?
C13 C14 1.511(6) . ?
C1 C2 1.351(6) . ?
C1 C6 1.384(7) . ?
C1 H1 0.9300 . ?
C7 C8 1.372(6) . ?
C7 C12 1.380(6) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C2 C3 1.359(6) . ?
C8 C9 1.381(7) . ?
C8 H8 0.9300 . ?
C12 C11 1.373(6) . ?
C12 H12 0.9300 . ?
C3 C4 1.369(8) . ?
C3 H3 0.9300 . ?
C11 C10 1.367(7) . ?
C11 H11 0.9300 . ?
C6 C5 1.358(10) . ?
C6 H6 0.9300 . ?
C10 C9 1.350(8) . ?
C10 H10 0.9300 . ?
C9 H9 0.9300 . ?
C4 C5 1.371(9) . ?
C4 H4 0.9300 . ?
C5 H5 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C14 S1 C14 102.0(4) . 2_656 ?
C13 N1 C7 121.7(4) . . ?
C13 N1 C2 121.8(4) . . ?
C7 N1 C2 116.3(4) . . ?
O1 C13 N1 122.2(5) . . ?
O1 C13 C14 122.8(4) . . ?
N1 C13 C14 114.9(4) . . ?
C2 C1 C6 119.9(6) . . ?
C2 C1 H1 120.1 . . ?
C6 C1 H1 120.1 . . ?
C8 C7 C12 119.2(5) . . ?
C8 C7 N1 119.6(4) . . ?
C12 C7 N1 121.2(4) . . ?
C13 C14 S1 115.5(3) . . ?
C13 C14 H14A 108.4 . . ?
S1 C14 H14A 108.4 . . ?
C13 C14 H14B 108.4 . . ?
S1 C14 H14B 108.4 . . ?
H14A C14 H14B 107.5 . . ?
C1 C2 C3 120.4(5) . . ?
C1 C2 N1 120.9(5) . . ?
C3 C2 N1 118.6(5) . . ?
C7 C8 C9 119.8(5) . . ?
C7 C8 H8 120.1 . . ?
C9 C8 H8 120.1 . . ?
C11 C12 C7 120.0(5) . . ?
C11 C12 H12 120.0 . . ?
C7 C12 H12 120.0 . . ?
C2 C3 C4 119.7(6) . . ?
C2 C3 H3 120.1 . . ?
C4 C3 H3 120.1 . . ?
C10 C11 C12 120.4(5) . . ?
C10 C11 H11 119.8 . . ?
C12 C11 H11 119.8 . . ?
C5 C6 C1 120.2(7) . . ?
C5 C6 H6 119.9 . . ?
C1 C6 H6 119.9 . . ?
C9 C10 C11 119.7(6) . . ?
C9 C10 H10 120.1 . . ?
C11 C10 H10 120.1 . . ?
C10 C9 C8 120.8(6) . . ?
C10 C9 H9 119.6 . . ?
C8 C9 H9 119.6 . . ?
C3 C4 C5 120.6(7) . . ?
C3 C4 H4 119.7 . . ?
C5 C4 H4 119.7 . . ?
C6 C5 C4 119.2(6) . . ?
C6 C5 H5 120.4 . . ?
C4 C5 H5 120.4 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C7 N1 C13 O1 -6.3(7) . . . . ?
C2 N1 C13 O1 179.4(5) . . . . ?
C7 N1 C13 C14 171.4(4) . . . . ?
C2 N1 C13 C14 -3.0(6) . . . . ?
C13 N1 C7 C8 131.2(5) . . . . ?
C2 N1 C7 C8 -54.1(6) . . . . ?
C13 N1 C7 C12 -49.7(6) . . . . ?
C2 N1 C7 C12 124.9(5) . . . . ?
O1 C13 C14 S1 -19.4(7) . . . . ?
N1 C13 C14 S1 163.0(3) . . . . ?
C14 S1 C14 C13 71.8(4) 2_656 . . . ?
C6 C1 C2 C3 -1.3(8) . . . . ?
C6 C1 C2 N1 179.1(4) . . . . ?
C13 N1 C2 C1 -86.4(6) . . . . ?
C7 N1 C2 C1 99.0(5) . . . . ?
C13 N1 C2 C3 94.0(6) . . . . ?
C7 N1 C2 C3 -80.6(5) . . . . ?
C12 C7 C8 C9 -0.8(8) . . . . ?
N1 C7 C8 C9 178.2(5) . . . . ?
C8 C7 C12 C11 0.2(7) . . . . ?
N1 C7 C12 C11 -178.8(4) . . . . ?
C1 C2 C3 C4 0.2(8) . . . . ?
N1 C2 C3 C4 179.8(5) . . . . ?
C7 C12 C11 C10 0.3(8) . . . . ?
C2 C1 C6 C5 1.5(9) . . . . ?
C12 C11 C10 C9 -0.1(9) . . . . ?
C11 C10 C9 C8 -0.5(10) . . . . ?
C7 C8 C9 C10 1.0(10) . . . . ?
C2 C3 C4 C5 0.8(10) . . . . ?
C1 C6 C5 C4 -0.5(10) . . . . ?
C3 C4 C5 C6 -0.6(11) . . . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        24.95
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.292
_refine_diff_density_min         -0.191
_refine_diff_density_rms         0.039
