# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2014

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
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#  data retrieval see:
#                         www.ccdc.cam.ac.uk
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#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
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data_I
#TrackingRef 'web_deposit_cif_file_0_MARIAANGELESFERNANDEZ_1362499951.datos monomer_0m.cif'

_chemical_name_systematic        ?
_chemical_name_common            TA523c
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H34 N4 O4 Pd S'
_chemical_formula_iupac          ?
_chemical_formula_weight         556.99
_chemical_absolute_configuration ?

_chemical_melting_point          ?

_space_group_crystal_system      orthorhombic
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'

_cell_length_a                   9.3740(3)
_cell_length_b                   14.5468(4)
_cell_length_c                   19.7294(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2690.33(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9063
_cell_measurement_theta_min      2.4055
_cell_measurement_theta_max      25.8223
_cell_measurement_temperature    296.(2)

_exptl_crystal_description       prismatic
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_size_max          0.340
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.160
_exptl_crystal_density_diffrn    1.375
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1152

_exptl_absorpt_coefficient_mu    0.799
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_correction_T_min  0.80
_exptl_absorpt_correction_T_max  0.88

_exptl_special_details           
;
;

_diffrn_ambient_temperature      296.(2)

_diffrn_source                   ?
_diffrn_source_type              ?

_diffrn_radiation_type           ?
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  ?

_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            103234
_diffrn_reflns_av_R_equivalents  0.0340
_diffrn_reflns_av_sigmaI/netI    0.0113
_diffrn_reflns_theta_min         1.74
_diffrn_reflns_theta_max         25.34
_diffrn_reflns_theta_full        25.34
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23

_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.
;

_reflns_number_total             4926
_reflns_number_gt                4704
_reflns_threshold_expression     >2sigma(I)

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0201
_refine_ls_R_factor_gt           0.0180
_refine_ls_wR_factor_gt          0.0462
_refine_ls_wR_factor_ref         0.0480
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_restrained_S_all      1.009
_refine_ls_number_reflns         4926
_refine_ls_number_parameters     298
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0281P)²+0.5812P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap

_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.164
_refine_diff_density_min         -0.277
_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   -0.047(19)

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'
Pd Pd -0.9988 1.0072 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       'Bruker Instrument Service v2010.9.0.0'
_computing_cell_refinement       'SAINT V7.68A (Bruker AXS, 2009)'
_computing_data_reduction        'SAINT V7.68A (Bruker AXS, 2009)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Pd Pd1 0.022156(15) 0.504088(10) 0.855961(7) 0.04261(5) Uani d . 1 . .
C C1 0.0003(3) 0.27078(13) 0.75409(11) 0.0484(5) Uani d . 1 . .
C C2 0.0968(4) 0.2653(2) 0.70218(17) 0.0826(9) Uani d . 1 . .
H H2 0.0973 0.3087 0.6676 0.099 Uiso calc R 1 . .
C C3 0.1926(4) 0.1941(3) 0.7026(2) 0.1118(15) Uani d . 1 . .
H H3 0.2592 0.1881 0.6679 0.134 Uiso calc R 1 . .
C C4 0.1890(3) 0.1327(2) 0.7539(2) 0.0945(12) Uani d . 1 . .
H H4 0.2534 0.0841 0.755 0.113 Uiso calc R 1 . .
C C5 0.0897(3) 0.14262(19) 0.80418(17) 0.0795(8) Uani d . 1 . .
H H5 0.0888 0.1 0.8393 0.095 Uiso calc R 1 . .
C C6 -0.2210(2) 0.37198(14) 0.87989(11) 0.0427(5) Uani d . 1 . .
H H6 -0.2241 0.3047 0.877 0.051 Uiso calc R 1 . .
C C7 -0.3707(3) 0.40911(17) 0.87026(12) 0.0563(6) Uani d . 1 . .
C C8 -0.6160(3) 0.3714(3) 0.8824(2) 0.1288(17) Uani d . 1 . .
H H8A -0.6383 0.4139 0.918 0.193 Uiso calc R 1 . .
H H8B -0.6752 0.3178 0.8867 0.193 Uiso calc R 1 . .
H H8C -0.6331 0.3999 0.8393 0.193 Uiso calc R 1 . .
C C9 -0.1555(3) 0.39962(17) 0.94911(11) 0.0549(6) Uani d . 1 . .
C C10 -0.2665(4) 0.3953(3) 1.00711(14) 0.0864(10) Uani d . 1 . .
H H10A -0.3404 0.4396 0.9989 0.13 Uiso calc R 1 . .
H H10B -0.2205 0.4087 1.0494 0.13 Uiso calc R 1 . .
H H10C -0.3074 0.3348 1.0089 0.13 Uiso calc R 1 . .
C C11 -0.0343(3) 0.33277(19) 0.96503(13) 0.0719(7) Uani d . 1 . .
H H11A -0.0727 0.2722 0.9715 0.108 Uiso calc R 1 . .
H H11B 0.0137 0.3521 1.0055 0.108 Uiso calc R 1 . .
H H11C 0.0321 0.332 0.928 0.108 Uiso calc R 1 . .
C C12 -0.0999(2) 0.49813(18) 0.94200(11) 0.0583(5) Uani d . 1 . .
H H12A -0.0431 0.5146 0.9813 0.07 Uiso calc R 1 . .
H H12B -0.1791 0.5408 0.9387 0.07 Uiso calc R 1 . .
C C13 0.1427(3) 0.59601(16) 0.89713(12) 0.0537(6) Uani d . 1 . .
C C14 0.3265(3) 0.71525(17) 0.94128(12) 0.0562(6) Uani d . 1 . .
C C15 0.3608(4) 0.6936(3) 1.01320(16) 0.1081(13) Uani d . 1 . .
H H15A 0.2742 0.6913 1.0392 0.162 Uiso calc R 1 . .
H H15B 0.4222 0.7403 1.0313 0.162 Uiso calc R 1 . .
H H15C 0.4079 0.6351 1.0156 0.162 Uiso calc R 1 . .
C C16 0.2647(3) 0.8118(2) 0.93669(17) 0.0820(9) Uani d . 1 . .
H H16A 0.2384 0.8246 0.8906 0.123 Uiso calc R 1 . .
H H16B 0.3348 0.8555 0.9514 0.123 Uiso calc R 1 . .
H H16C 0.1819 0.8161 0.9652 0.123 Uiso calc R 1 . .
C C17 0.4511(3) 0.7065(2) 0.89294(17) 0.0815(9) Uani d . 1 . .
H H17A 0.4879 0.645 0.8946 0.122 Uiso calc R 1 . .
H H17B 0.5246 0.749 0.9058 0.122 Uiso calc R 1 . .
H H17C 0.4198 0.7201 0.8477 0.122 Uiso calc R 1 . .
C C18 0.1506(2) 0.50828(16) 0.77075(10) 0.0496(5) Uani d . 1 . .
C C19 0.3329(3) 0.53160(16) 0.67271(12) 0.0593(6) Uani d . 1 . .
C C20 0.4221(4) 0.4460(2) 0.6660(2) 0.1122(14) Uani d . 1 . .
H H20A 0.4723 0.4351 0.7076 0.168 Uiso calc R 1 . .
H H20B 0.4896 0.4538 0.6298 0.168 Uiso calc R 1 . .
H H20C 0.3614 0.3945 0.6562 0.168 Uiso calc R 1 . .
C C21 0.2437(4) 0.5510(3) 0.61022(16) 0.1070(14) Uani d . 1 . .
H H21A 0.1772 0.5017 0.6034 0.16 Uiso calc R 1 . .
H H21B 0.305 0.5561 0.5714 0.16 Uiso calc R 1 . .
H H21C 0.1925 0.6076 0.6163 0.16 Uiso calc R 1 . .
C C22 0.4223(4) 0.6141(2) 0.69033(17) 0.0876(10) Uani d . 1 . .
H H22A 0.3614 0.6664 0.6971 0.131 Uiso calc R 1 . .
H H22B 0.4876 0.6266 0.654 0.131 Uiso calc R 1 . .
H H22C 0.4748 0.6021 0.7311 0.131 Uiso calc R 1 . .
N N1 -0.0064(3) 0.21109(13) 0.80519(11) 0.0630(5) Uani d . 1 . .
N N2 -0.12452(19) 0.40674(11) 0.82729(8) 0.0416(4) Uani d . 1 . .
N N3 0.2164(2) 0.65062(15) 0.91873(11) 0.0612(5) Uani d . 1 . .
N N4 0.2317(2) 0.51670(13) 0.72842(9) 0.0531(5) Uani d . 1 . .
O O1 -0.0926(2) 0.42063(11) 0.70266(8) 0.0650(5) Uani d . 1 . .
O O2 -0.26825(18) 0.31176(11) 0.74849(9) 0.0579(4) Uani d . 1 . .
O O3 -0.46749(18) 0.34485(13) 0.88718(10) 0.0735(5) Uani d . 1 . .
O O4 -0.4019(2) 0.48485(13) 0.85199(12) 0.0865(6) Uani d . 1 . .
S S1 -0.13348(7) 0.35858(3) 0.75566(3) 0.04524(13) Uani d . 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Pd1 C13 . 1.930(2) ?
Pd1 C12 . 2.0491(19) ?
Pd1 N2 . 2.0532(17) ?
Pd1 C18 . 2.069(2) ?
C1 N1 . 1.332(3) ?
C1 C2 . 1.369(4) ?
C1 S1 . 1.790(2) ?
C2 C3 . 1.372(5) ?
C2 H2 . 0.93 ?
C3 C4 . 1.350(6) ?
C3 H3 . 0.93 ?
C4 C5 . 1.368(5) ?
C4 H4 . 0.93 ?
C5 N1 . 1.343(3) ?
C5 H5 . 0.93 ?
C6 N2 . 1.466(3) ?
C6 C7 . 1.516(3) ?
C6 C9 . 1.550(3) ?
C6 H6 . 0.98 ?
C7 O4 . 1.195(3) ?
C7 O3 . 1.345(3) ?
C8 O3 . 1.448(3) ?
C8 H8A . 0.96 ?
C8 H8B . 0.96 ?
C8 H8C . 0.96 ?
C9 C11 . 1.528(4) ?
C9 C12 . 1.531(4) ?
C9 C10 . 1.548(3) ?
C10 H10A . 0.96 ?
C10 H10B . 0.96 ?
C10 H10C . 0.96 ?
C11 H11A . 0.96 ?
C11 H11B . 0.96 ?
C11 H11C . 0.96 ?
C12 H12A . 0.97 ?
C12 H12B . 0.97 ?
C13 N3 . 1.136(3) ?
C14 N3 . 1.465(3) ?
C14 C15 . 1.489(4) ?
C14 C17 . 1.513(4) ?
C14 C16 . 1.522(4) ?
C15 H15A . 0.96 ?
C15 H15B . 0.96 ?
C15 H15C . 0.96 ?
C16 H16A . 0.96 ?
C16 H16B . 0.96 ?
C16 H16C . 0.96 ?
C17 H17A . 0.96 ?
C17 H17B . 0.96 ?
C17 H17C . 0.96 ?
C18 N4 . 1.136(3) ?
C19 N4 . 1.468(3) ?
C19 C22 . 1.505(4) ?
C19 C20 . 1.506(4) ?
C19 C21 . 1.516(4) ?
C20 H20A . 0.96 ?
C20 H20B . 0.96 ?
C20 H20C . 0.96 ?
C21 H21A . 0.96 ?
C21 H21B . 0.96 ?
C21 H21C . 0.96 ?
C22 H22A . 0.96 ?
C22 H22B . 0.96 ?
C22 H22C . 0.96 ?
N2 S1 . 1.5797(16) ?
O1 S1 . 1.4335(16) ?
O2 S1 . 1.4421(17) ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C13 Pd1 C12 . . 90.43(10) ?
C13 Pd1 N2 . . 170.36(8) ?
C12 Pd1 N2 . . 79.92(8) ?
C13 Pd1 C18 . . 88.91(9) ?
C12 Pd1 C18 . . 178.22(9) ?
N2 Pd1 C18 . . 100.73(8) ?
N1 C1 C2 . . 124.0(2) ?
N1 C1 S1 . . 114.79(18) ?
C2 C1 S1 . . 121.2(2) ?
C1 C2 C3 . . 118.2(3) ?
C1 C2 H2 . . 120.9 ?
C3 C2 H2 . . 120.9 ?
C4 C3 C2 . . 119.2(3) ?
C4 C3 H3 . . 120.4 ?
C2 C3 H3 . . 120.4 ?
C3 C4 C5 . . 119.5(3) ?
C3 C4 H4 . . 120.3 ?
C5 C4 H4 . . 120.3 ?
N1 C5 C4 . . 123.0(3) ?
N1 C5 H5 . . 118.5 ?
C4 C5 H5 . . 118.5 ?
N2 C6 C7 . . 111.07(18) ?
N2 C6 C9 . . 106.84(17) ?
C7 C6 C9 . . 112.61(19) ?
N2 C6 H6 . . 108.7 ?
C7 C6 H6 . . 108.7 ?
C9 C6 H6 . . 108.7 ?
O4 C7 O3 . . 123.4(2) ?
O4 C7 C6 . . 126.3(2) ?
O3 C7 C6 . . 110.23(19) ?
O3 C8 H8A . . 109.5 ?
O3 C8 H8B . . 109.5 ?
H8A C8 H8B . . 109.5 ?
O3 C8 H8C . . 109.5 ?
H8A C8 H8C . . 109.5 ?
H8B C8 H8C . . 109.5 ?
C11 C9 C12 . . 111.2(2) ?
C11 C9 C10 . . 108.8(2) ?
C12 C9 C10 . . 109.6(2) ?
C11 C9 C6 . . 108.1(2) ?
C12 C9 C6 . . 107.27(19) ?
C10 C9 C6 . . 112.0(2) ?
C9 C10 H10A . . 109.5 ?
C9 C10 H10B . . 109.5 ?
H10A C10 H10B . . 109.5 ?
C9 C10 H10C . . 109.5 ?
H10A C10 H10C . . 109.5 ?
H10B C10 H10C . . 109.5 ?
C9 C11 H11A . . 109.5 ?
C9 C11 H11B . . 109.5 ?
H11A C11 H11B . . 109.5 ?
C9 C11 H11C . . 109.5 ?
H11A C11 H11C . . 109.5 ?
H11B C11 H11C . . 109.5 ?
C9 C12 Pd1 . . 107.79(14) ?
C9 C12 H12A . . 110.1 ?
Pd1 C12 H12A . . 110.1 ?
C9 C12 H12B . . 110.1 ?
Pd1 C12 H12B . . 110.1 ?
H12A C12 H12B . . 108.5 ?
N3 C13 Pd1 . . 177.0(2) ?
N3 C14 C15 . . 107.8(2) ?
N3 C14 C17 . . 107.4(2) ?
C15 C14 C17 . . 114.6(3) ?
N3 C14 C16 . . 107.8(2) ?
C15 C14 C16 . . 109.5(3) ?
C17 C14 C16 . . 109.5(2) ?
C14 C15 H15A . . 109.5 ?
C14 C15 H15B . . 109.5 ?
H15A C15 H15B . . 109.5 ?
C14 C15 H15C . . 109.5 ?
H15A C15 H15C . . 109.5 ?
H15B C15 H15C . . 109.5 ?
C14 C16 H16A . . 109.5 ?
C14 C16 H16B . . 109.5 ?
H16A C16 H16B . . 109.5 ?
C14 C16 H16C . . 109.5 ?
H16A C16 H16C . . 109.5 ?
H16B C16 H16C . . 109.5 ?
C14 C17 H17A . . 109.5 ?
C14 C17 H17B . . 109.5 ?
H17A C17 H17B . . 109.5 ?
C14 C17 H17C . . 109.5 ?
H17A C17 H17C . . 109.5 ?
H17B C17 H17C . . 109.5 ?
N4 C18 Pd1 . . 171.94(19) ?
N4 C19 C22 . . 107.7(2) ?
N4 C19 C20 . . 107.6(2) ?
C22 C19 C20 . . 111.8(3) ?
N4 C19 C21 . . 106.3(2) ?
C22 C19 C21 . . 110.3(3) ?
C20 C19 C21 . . 112.9(3) ?
C19 C20 H20A . . 109.5 ?
C19 C20 H20B . . 109.5 ?
H20A C20 H20B . . 109.5 ?
C19 C20 H20C . . 109.5 ?
H20A C20 H20C . . 109.5 ?
H20B C20 H20C . . 109.5 ?
C19 C21 H21A . . 109.5 ?
C19 C21 H21B . . 109.5 ?
H21A C21 H21B . . 109.5 ?
C19 C21 H21C . . 109.5 ?
H21A C21 H21C . . 109.5 ?
H21B C21 H21C . . 109.5 ?
C19 C22 H22A . . 109.5 ?
C19 C22 H22B . . 109.5 ?
H22A C22 H22B . . 109.5 ?
C19 C22 H22C . . 109.5 ?
H22A C22 H22C . . 109.5 ?
H22B C22 H22C . . 109.5 ?
C1 N1 C5 . . 116.2(3) ?
C6 N2 S1 . . 116.57(14) ?
C6 N2 Pd1 . . 117.13(12) ?
S1 N2 Pd1 . . 126.01(10) ?
C13 N3 C14 . . 172.4(3) ?
C18 N4 C19 . . 177.3(2) ?
C7 O3 C8 . . 116.6(2) ?
O1 S1 O2 . . 117.38(11) ?
O1 S1 N2 . . 111.05(9) ?
O2 S1 N2 . . 110.10(10) ?
O1 S1 C1 . . 104.45(11) ?
O2 S1 C1 . . 105.96(10) ?
N2 S1 C1 . . 107.14(10) ?



_database_code_depnum_ccdc_archive 'CCDC 928003'
