# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2018

####################################################################### 
# 
# 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_shrv450
_database_code_depnum_ccdc_archive 'CCDC 1578028'
_audit_update_record             
;
2017-10-04 deposited with the CCDC.
2018-08-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 H8 N18 Pd, 4(C2 H6 O S)'
_chemical_formula_sum            'C14 H32 N18 O4 Pd S4'
_chemical_formula_weight         751.21

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'
Pd Pd 0.1215 3.9337 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.0774(6)
_cell_length_b                   9.3329(7)
_cell_length_c                   10.9899(8)
_cell_angle_alpha                96.638(3)
_cell_angle_beta                 108.728(3)
_cell_angle_gamma                107.974(4)
_cell_volume                     724.82(10)
_cell_formula_units_Z            1
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    4417
_cell_measurement_theta_min      4.374
_cell_measurement_theta_max      75.124

_exptl_crystal_description       chunk
_exptl_crystal_colour            'clear colorless'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.721
_exptl_crystal_F_000             384
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.084
_exptl_crystal_size_mid          0.076
_exptl_crystal_size_min          0.035
_exptl_absorpt_coefficient_mu    8.373
_shelx_estimated_absorpt_T_min   0.540
_shelx_estimated_absorpt_T_max   0.758
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5208
_exptl_absorpt_correction_T_max  0.7538
_exptl_absorpt_process_details   'SADABS v2014/5 (Bruker, 2008)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   '1uS microfocus'
_diffrn_radiation_monochromator  'HELIOS multilayer optics'
_diffrn_measurement_device_type  'Photon 100'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4883
_diffrn_reflns_av_unetI/netI     0.0482
_diffrn_reflns_av_R_equivalents  0.0356
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         4.374
_diffrn_reflns_theta_max         75.115
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.789
_diffrn_measured_fraction_theta_full 0.835
_diffrn_reflns_Laue_measured_fraction_max 0.789
_diffrn_reflns_Laue_measured_fraction_full 0.835
_diffrn_reflns_point_group_measured_fraction_max 0.789
_diffrn_reflns_point_group_measured_fraction_full 0.835
_reflns_number_total             2359
_reflns_number_gt                2188
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX3 v2015.5-2 (Bruker, 2015)'
_computing_cell_refinement       'Bruker APEX3 v2015.5-2 (Bruker, 2015)'
_computing_data_reduction        
;
Bruker SAINT v8.34A (Bruker, 2013), Bruker XPREP v2014/2 (Bruker, 2014)
;
_computing_structure_solution    'Bruker SHELXTL v2014/7 (Bruker, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL v2014/7 (Bruker, 2014)'
_computing_publication_material  'Bruker SHELXTL v2014/7 (Bruker, 2014)'
_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)+(0.0557P)²+4.3391P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2359
_refine_ls_number_parameters     193
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0584
_refine_ls_R_factor_gt           0.0531
_refine_ls_wR_factor_ref         0.1337
_refine_ls_wR_factor_gt          0.1272
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_restrained_S_all      1.084
_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
N1 N 0.4632(7) 0.3140(6) 0.0787(5) 0.0213(10) Uani 1 1 d . . . . .
N2 N 0.3751(7) 0.1628(6) 0.0091(5) 0.0283(11) Uani 1 1 d . . . . .
N3 N 0.3976(8) 0.0769(6) 0.0932(5) 0.0302(12) Uani 1 1 d . . . . .
N4 N 0.5004(7) 0.1675(6) 0.2193(5) 0.0254(11) Uani 1 1 d . . . . .
C5 C 0.5360(8) 0.3105(7) 0.2043(6) 0.0218(12) Uani 1 1 d . . . . .
C6 C 0.6471(8) 0.4560(7) 0.3148(6) 0.0243(13) Uani 1 1 d . . . . .
H6 H 0.5589 0.5041 0.3308 0.029 Uiso 1 1 calc R U . . .
N7 N 0.7457(7) 0.4182(6) 0.4366(5) 0.0267(11) Uani 1 1 d . . . . .
H7A H 0.8160 0.3644 0.4201 0.040 Uiso 1 1 calc R U . . .
H7B H 0.6603 0.3593 0.4657 0.040 Uiso 1 1 calc R U . . .
H7C H 0.8220 0.5073 0.4996 0.040 Uiso 1 1 calc R U . . .
C8 C 0.7878(8) 0.5695(7) 0.2762(6) 0.0206(12) Uani 1 1 d . . . . .
N9 N 0.9644(7) 0.6525(6) 0.3521(5) 0.0255(11) Uani 1 1 d . . . . .
N10 N 1.0333(7) 0.7369(6) 0.2738(5) 0.0273(11) Uani 1 1 d . . . . .
N11 N 0.9017(7) 0.7055(6) 0.1559(5) 0.0237(11) Uani 1 1 d . . . . .
N12 N 0.7430(7) 0.5993(5) 0.1554(5) 0.0193(10) Uani 1 1 d . . . . .
Pd13 Pd 0.5000 0.5000 0.0000 0.0199(2) Uani 1 2 d S . P . .
C14 C 0.2657(9) 0.0385(9) 0.5834(7) 0.0387(17) Uani 1 1 d . . . . .
H14A H 0.2026 0.1071 0.6036 0.058 Uiso 1 1 calc R U . . .
H14B H 0.2653 -0.0338 0.6413 0.058 Uiso 1 1 calc R U . . .
H14C H 0.1991 -0.0200 0.4908 0.058 Uiso 1 1 calc R U . . .
S15 S 0.5028(2) 0.15187(18) 0.60954(15) 0.0272(4) Uani 1 1 d . . . . .
O16 O 0.4910(7) 0.2858(6) 0.5444(5) 0.0374(11) Uani 1 1 d . . . . .
C17 C 0.5833(9) 0.2323(8) 0.7809(6) 0.0308(14) Uani 1 1 d . . . . .
H17A H 0.7091 0.3125 0.8106 0.046 Uiso 1 1 calc R U . . .
H17B H 0.5884 0.1506 0.8290 0.046 Uiso 1 1 calc R U . . .
H17C H 0.4969 0.2785 0.7983 0.046 Uiso 1 1 calc R U . . .
C18 C 1.0639(12) 0.6966(9) 0.8985(7) 0.0426(18) Uani 1 1 d . . . . .
H18A H 1.0674 0.5921 0.8928 0.064 Uiso 1 1 calc R U . . .
H18B H 1.0274 0.7240 0.9722 0.064 Uiso 1 1 calc R U . . .
H18C H 1.1885 0.7711 0.9133 0.064 Uiso 1 1 calc R U . . .
S19 S 0.8977(2) 0.70134(19) 0.74864(16) 0.0305(4) Uani 1 1 d . . . . .
O20 O 0.9747(6) 0.6748(5) 0.6427(4) 0.0329(10) Uani 1 1 d . . . . .
C21 C 0.9414(11) 0.9020(9) 0.7861(8) 0.0415(17) Uani 1 1 d . . . . .
H21A H 1.0740 0.9609 0.8051 0.062 Uiso 1 1 calc R U . . .
H21B H 0.9119 0.9284 0.8635 0.062 Uiso 1 1 calc R U . . .
H21C H 0.8624 0.9280 0.7103 0.062 Uiso 1 1 calc R U . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N1 0.022(3) 0.020(3) 0.018(3) 0.0036(18) 0.0039(19) 0.008(2)
N2 0.029(3) 0.026(3) 0.019(3) 0.001(2) 0.004(2) 0.004(2)
N3 0.036(3) 0.023(3) 0.025(3) 0.007(2) 0.009(2) 0.005(2)
N4 0.029(3) 0.018(3) 0.022(3) 0.006(2) 0.005(2) 0.004(2)
C5 0.021(3) 0.027(3) 0.015(3) 0.005(2) 0.006(2) 0.006(3)
C6 0.023(3) 0.025(3) 0.018(3) 0.003(2) 0.004(2) 0.004(3)
N7 0.023(3) 0.031(3) 0.019(3) 0.007(2) 0.006(2) 0.004(2)
C8 0.019(3) 0.024(3) 0.012(3) 0.003(2) 0.001(2) 0.003(3)
N9 0.023(3) 0.024(3) 0.022(3) 0.008(2) 0.005(2) 0.001(2)
N10 0.019(3) 0.024(3) 0.032(3) 0.008(2) 0.007(2) 0.000(2)
N11 0.020(3) 0.020(3) 0.026(3) 0.007(2) 0.008(2) 0.002(2)
N12 0.019(3) 0.018(2) 0.018(3) 0.0058(18) 0.008(2) 0.001(2)
Pd13 0.0213(4) 0.0208(3) 0.0161(3) 0.0057(2) 0.0057(2) 0.0066(3)
C14 0.021(4) 0.043(4) 0.041(4) 0.010(3) 0.010(3) -0.001(3)
S15 0.0264(8) 0.0288(8) 0.0245(9) 0.0031(6) 0.0123(6) 0.0059(7)
O16 0.042(3) 0.042(3) 0.029(3) 0.017(2) 0.019(2) 0.008(2)
C17 0.034(4) 0.032(4) 0.028(4) 0.007(3) 0.013(3) 0.011(3)
C18 0.059(5) 0.043(4) 0.035(4) 0.013(3) 0.022(4) 0.023(4)
S19 0.0299(9) 0.0289(8) 0.0252(9) 0.0001(6) 0.0105(7) 0.0030(7)
O20 0.036(3) 0.035(3) 0.020(2) -0.0019(18) 0.0120(19) 0.005(2)
C21 0.046(5) 0.034(4) 0.037(4) 0.001(3) 0.011(3) 0.012(3)

_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
N1 C5 1.324(8) . ?
N1 N2 1.365(7) . ?
N1 Pd13 2.010(5) . ?
N2 N3 1.297(7) . ?
N3 N4 1.372(7) . ?
N4 C5 1.318(8) . ?
C5 C6 1.514(8) . ?
C6 N7 1.466(7) . ?
C6 C8 1.505(8) . ?
C6 H6 1.0000 . ?
N7 H7A 0.9100 . ?
N7 H7B 0.9100 . ?
N7 H7C 0.9100 . ?
C8 N9 1.317(8) . ?
C8 N12 1.346(8) . ?
N9 N10 1.365(7) . ?
N10 N11 1.316(7) . ?
N11 N12 1.355(7) . ?
N12 Pd13 1.996(5) . ?
Pd13 N12 1.996(5) 2_665 ?
Pd13 N1 2.010(5) 2_665 ?
C14 S15 1.788(7) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
S15 O16 1.523(5) . ?
S15 C17 1.766(6) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 S19 1.775(8) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
S19 O20 1.516(4) . ?
S19 C21 1.767(7) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C5 N1 N2 105.9(5) . . ?
C5 N1 Pd13 127.9(4) . . ?
N2 N1 Pd13 125.7(4) . . ?
N3 N2 N1 107.6(5) . . ?
N2 N3 N4 110.5(5) . . ?
C5 N4 N3 104.1(5) . . ?
N4 C5 N1 111.9(5) . . ?
N4 C5 C6 125.3(5) . . ?
N1 C5 C6 122.8(5) . . ?
N7 C6 C8 109.4(5) . . ?
N7 C6 C5 110.3(5) . . ?
C8 C6 C5 109.7(5) . . ?
N7 C6 H6 109.1 . . ?
C8 C6 H6 109.1 . . ?
C5 C6 H6 109.1 . . ?
C6 N7 H7A 109.5 . . ?
C6 N7 H7B 109.5 . . ?
H7A N7 H7B 109.5 . . ?
C6 N7 H7C 109.5 . . ?
H7A N7 H7C 109.5 . . ?
H7B N7 H7C 109.5 . . ?
N9 C8 N12 111.4(5) . . ?
N9 C8 C6 126.4(5) . . ?
N12 C8 C6 122.2(5) . . ?
C8 N9 N10 104.6(5) . . ?
N11 N10 N9 110.5(5) . . ?
N10 N11 N12 107.5(5) . . ?
C8 N12 N11 106.0(5) . . ?
C8 N12 Pd13 128.2(4) . . ?
N11 N12 Pd13 125.6(4) . . ?
N12 Pd13 N12 180.0 . 2_665 ?
N12 Pd13 N1 85.89(19) . . ?
N12 Pd13 N1 94.11(19) 2_665 . ?
N12 Pd13 N1 94.11(19) . 2_665 ?
N12 Pd13 N1 85.89(19) 2_665 2_665 ?
N1 Pd13 N1 180.0 . 2_665 ?
S15 C14 H14A 109.5 . . ?
S15 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
S15 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
O16 S15 C17 105.1(3) . . ?
O16 S15 C14 105.4(3) . . ?
C17 S15 C14 98.2(3) . . ?
S15 C17 H17A 109.5 . . ?
S15 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
S15 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
S19 C18 H18A 109.5 . . ?
S19 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
S19 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
O20 S19 C21 106.1(3) . . ?
O20 S19 C18 106.1(3) . . ?
C21 S19 C18 97.7(4) . . ?
S19 C21 H21A 109.5 . . ?
S19 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
S19 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 N1 N2 N3 0.1(6) . . . . ?
Pd13 N1 N2 N3 173.0(4) . . . . ?
N1 N2 N3 N4 -0.1(7) . . . . ?
N2 N3 N4 C5 0.1(7) . . . . ?
N3 N4 C5 N1 -0.1(7) . . . . ?
N3 N4 C5 C6 -179.9(5) . . . . ?
N2 N1 C5 N4 0.0(7) . . . . ?
Pd13 N1 C5 N4 -172.7(4) . . . . ?
N2 N1 C5 C6 179.8(5) . . . . ?
Pd13 N1 C5 C6 7.1(8) . . . . ?
N4 C5 C6 N7 12.8(8) . . . . ?
N1 C5 C6 N7 -166.9(5) . . . . ?
N4 C5 C6 C8 133.5(6) . . . . ?
N1 C5 C6 C8 -46.2(7) . . . . ?
N7 C6 C8 N9 -15.3(8) . . . . ?
C5 C6 C8 N9 -136.5(6) . . . . ?
N7 C6 C8 N12 165.5(5) . . . . ?
C5 C6 C8 N12 44.4(8) . . . . ?
N12 C8 N9 N10 -0.7(7) . . . . ?
C6 C8 N9 N10 -179.9(6) . . . . ?
C8 N9 N10 N11 0.3(6) . . . . ?
N9 N10 N11 N12 0.2(6) . . . . ?
N9 C8 N12 N11 0.8(7) . . . . ?
C6 C8 N12 N11 -180.0(5) . . . . ?
N9 C8 N12 Pd13 176.9(4) . . . . ?
C6 C8 N12 Pd13 -3.9(8) . . . . ?
N10 N11 N12 C8 -0.6(6) . . . . ?
N10 N11 N12 Pd13 -176.8(4) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N7 H7A O20 0.91 2.13 2.985(7) 155.9 2_766
N7 H7B S15 0.91 2.89 3.757(5) 160.1 .
N7 H7B O16 0.91 1.85 2.738(7) 166.2 .
N7 H7C S19 0.91 2.87 3.667(5) 147.0 .
N7 H7C O20 0.91 1.85 2.758(7) 173.1 .

_refine_diff_density_max         0.683
_refine_diff_density_min         -1.476
_refine_diff_density_rms         0.145

# start Validation Reply Form
_vrf_PLAT029_shrv450             
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.835 Note  
RESPONSE: Low data completeness is a common problem encountered 
in triclinic unit cells when utilizing Cu radiation.
;
# end Validation Reply Form

# start Validation Reply Form
_vrf_PLAT015_shrv450             
;
PROBLEM: No _shelx_hkl_file record in SHELXL20xy CIF ....     Please Do ! 
RESPONSE: It is our policy to routinely not supply the HKL file unless 
specifically required.
;
####################################################################### 
# 
# 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_shrv434
_database_code_depnum_ccdc_archive 'CCDC 1578029'
_audit_update_record             
;
2017-10-04 deposited with the CCDC.
2018-08-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C3 H2 N9 O2, Na, H2 O'
_chemical_formula_sum            'C3 H4 N9 Na O3'
_chemical_formula_weight         237.14

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'
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'
Na Na 0.0362 0.0249 '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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           57
_space_group_name_H-M_alt        'P b c m'
_space_group_name_Hall           '-P 2c 2b'

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

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

_cell_length_a                   8.3610(11)
_cell_length_b                   15.124(2)
_cell_length_c                   6.2921(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     795.62(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    1746
_cell_measurement_theta_min      2.436
_cell_measurement_theta_max      27.775

_exptl_crystal_description       needle
_exptl_crystal_colour            'clear colorless'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.980
_exptl_crystal_F_000             480
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.259
_exptl_crystal_size_mid          0.049
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    0.215
_shelx_estimated_absorpt_T_min   0.947
_shelx_estimated_absorpt_T_max   0.991
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6878
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_process_details   'SADABS v2014/5 (Bruker, 2008)'
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker SMART APEX II CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8493
_diffrn_reflns_av_unetI/netI     0.0263
_diffrn_reflns_av_R_equivalents  0.0424
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         2.784
_diffrn_reflns_theta_max         30.000
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             1239
_reflns_number_gt                936
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX3 v2015.5-2 (Bruker, 2015)'
_computing_cell_refinement       'Bruker APEX3 v2015.5-2 (Bruker, 2015)'
_computing_data_reduction        
;
Bruker SAINT v8.34A (Bruker, 2013), Bruker XPREP v2014/2 (Bruker, 2014)
;
_computing_structure_solution    'Bruker SHELXTL v2014/7 (Bruker, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL v2014/7 (Bruker, 2014)'
_computing_publication_material  'Bruker SHELXTL v2014/7 (Bruker, 2014)'
_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)+(0.0461P)²+0.1737P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1239
_refine_ls_number_parameters     100
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0557
_refine_ls_R_factor_gt           0.0346
_refine_ls_wR_factor_ref         0.0913
_refine_ls_wR_factor_gt          0.0828
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_restrained_S_all      1.069
_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
N1 N 0.78276(18) 0.64313(10) 0.7500 0.0141(3) Uani 1 2 d S T P . .
H1 H 0.8561 0.6014 0.7500 0.017 Uiso 1 2 calc R U P . .
N2 N 0.81161(19) 0.73035(10) 0.7500 0.0157(4) Uani 1 2 d S T P . .
N3 N 0.67420(19) 0.76912(11) 0.7500 0.0165(4) Uani 1 2 d S T P . .
N4 N 0.55251(19) 0.70908(10) 0.7500 0.0141(3) Uani 1 2 d S T P . .
C5 C 0.6228(2) 0.62956(12) 0.7500 0.0117(4) Uani 1 2 d S T P . .
C6 C 0.5419(2) 0.54544(12) 0.7500 0.0122(4) Uani 1 2 d S T P . .
N7 N 0.63245(19) 0.47071(10) 0.7500 0.0140(3) Uani 1 2 d S T P . .
O8 O 0.78386(16) 0.47624(9) 0.7500 0.0185(3) Uani 1 2 d S T P . .
O9 O 0.56665(16) 0.39484(9) 0.7500 0.0195(3) Uani 1 2 d S T P . .
C10 C 0.3693(2) 0.53787(12) 0.7500 0.0126(4) Uani 1 2 d S T P . .
N11 N 0.26451(19) 0.60471(11) 0.7500 0.0160(4) Uani 1 2 d S T P . .
N12 N 0.11646(19) 0.56558(11) 0.7500 0.0171(4) Uani 1 2 d S T P . .
N13 N 0.12849(19) 0.48054(11) 0.7500 0.0161(4) Uani 1 2 d S T P . .
N14 N 0.28552(18) 0.46187(10) 0.7500 0.0136(3) Uani 1 2 d S T P . .
H14 H 0.3271 0.4084 0.7500 0.016 Uiso 1 2 calc R U P . .
Na15 Na 0.31131(10) 0.7500 0.5000 0.0272(2) Uani 1 2 d S T P . .
O16 O 0.12891(17) 0.69862(10) 0.2500 0.0251(4) Uani 1 2 d DS T P . .
H16B H 0.0362(16) 0.7188(15) 0.2500 0.038 Uiso 1 2 d DS U P . .
H16A H 0.139(3) 0.6436(7) 0.2500 0.038 Uiso 1 2 d DS U P . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N1 0.0108(7) 0.0093(8) 0.0222(8) 0.000 0.000 -0.0006(6)
N2 0.0137(8) 0.0100(8) 0.0235(9) 0.000 0.000 -0.0007(6)
N3 0.0143(8) 0.0117(8) 0.0234(9) 0.000 0.000 -0.0012(6)
N4 0.0113(8) 0.0102(8) 0.0209(8) 0.000 0.000 -0.0010(6)
C5 0.0111(8) 0.0116(8) 0.0125(8) 0.000 0.000 0.0005(7)
C6 0.0100(9) 0.0093(8) 0.0173(9) 0.000 0.000 0.0001(7)
N7 0.0110(8) 0.0103(7) 0.0207(8) 0.000 0.000 -0.0006(6)
O8 0.0076(6) 0.0135(7) 0.0343(8) 0.000 0.000 0.0005(5)
O9 0.0142(7) 0.0070(6) 0.0372(9) 0.000 0.000 -0.0018(5)
C10 0.0109(9) 0.0118(9) 0.0150(9) 0.000 0.000 0.0005(7)
N11 0.0099(8) 0.0121(8) 0.0261(9) 0.000 0.000 0.0009(6)
N12 0.0100(8) 0.0149(8) 0.0264(9) 0.000 0.000 -0.0012(6)
N13 0.0089(8) 0.0148(8) 0.0247(9) 0.000 0.000 0.0016(6)
N14 0.0095(7) 0.0100(8) 0.0212(8) 0.000 0.000 -0.0003(6)
Na15 0.0156(4) 0.0363(5) 0.0297(5) 0.0105(4) 0.000 0.000
O16 0.0130(7) 0.0128(7) 0.0496(10) 0.000 0.000 0.0028(6)

_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
N1 N2 1.341(2) . ?
N1 C5 1.353(2) . ?
N1 H1 0.8800 . ?
N2 N3 1.290(2) . ?
N3 N4 1.364(2) . ?
N4 C5 1.339(2) . ?
N4 Na15 2.6314(14) . ?
C5 C6 1.441(3) . ?
C6 N7 1.360(2) . ?
C6 C10 1.448(3) . ?
N7 O8 1.269(2) . ?
N7 O9 1.272(2) . ?
O9 Na15 2.8833(12) 5_666 ?
C10 N11 1.338(2) . ?
C10 N14 1.346(2) . ?
N11 N12 1.372(2) . ?
N11 Na15 2.7305(13) . ?
N12 N13 1.290(2) . ?
N13 N14 1.343(2) . ?
N14 H14 0.8800 . ?
Na15 O16 2.3247(12) . ?
Na15 N4 2.6314(14) 7_575 ?
Na15 N11 2.7305(13) 7_575 ?
Na15 O9 2.8833(12) 3_656 ?
Na15 H16A 2.672(17) . ?
O16 Na15 2.3247(12) 6_556 ?
O16 H16B 0.833(9) . ?
O16 H16A 0.836(10) . ?

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
N2 N1 C5 109.08(15) . . ?
N2 N1 H1 125.5 . . ?
C5 N1 H1 125.5 . . ?
N3 N2 N1 106.68(15) . . ?
N2 N3 N4 111.21(15) . . ?
C5 N4 N3 105.70(15) . . ?
N4 C5 N1 107.33(16) . . ?
N4 C5 C6 125.95(16) . . ?
N1 C5 C6 126.72(17) . . ?
N7 C6 C5 118.19(16) . . ?
N7 C6 C10 119.27(16) . . ?
C5 C6 C10 122.53(16) . . ?
O8 N7 O9 119.40(15) . . ?
O8 N7 C6 120.03(16) . . ?
O9 N7 C6 120.57(15) . . ?
N11 C10 N14 107.72(16) . . ?
N11 C10 C6 126.38(17) . . ?
N14 C10 C6 125.90(17) . . ?
C10 N11 N12 105.36(15) . . ?
N13 N12 N11 111.08(15) . . ?
N12 N13 N14 106.61(15) . . ?
N13 N14 C10 109.23(15) . . ?
N13 N14 H14 125.4 . . ?
C10 N14 H14 125.4 . . ?
Na15 O16 H16B 119.2(11) 6_556 . ?
Na15 O16 H16A 105.5(12) 6_556 . ?
H16B O16 H16A 117(2) . . ?

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
C5 N1 N2 N3 0.0 . . . . ?
N1 N2 N3 N4 0.0 . . . . ?
N2 N3 N4 C5 0.0 . . . . ?
N3 N4 C5 N1 0.0 . . . . ?
N3 N4 C5 C6 180.0 . . . . ?
N2 N1 C5 N4 0.0 . . . . ?
N2 N1 C5 C6 180.0 . . . . ?
N4 C5 C6 N7 180.0 . . . . ?
N1 C5 C6 N7 0.0 . . . . ?
N4 C5 C6 C10 0.0 . . . . ?
N1 C5 C6 C10 180.0 . . . . ?
C5 C6 N7 O8 0.0 . . . . ?
C10 C6 N7 O8 180.0 . . . . ?
C5 C6 N7 O9 180.0 . . . . ?
C10 C6 N7 O9 0.0 . . . . ?
N7 C6 C10 N11 180.0 . . . . ?
C5 C6 C10 N11 0.0 . . . . ?
N7 C6 C10 N14 0.0 . . . . ?
C5 C6 C10 N14 180.0 . . . . ?
N14 C10 N11 N12 0.0 . . . . ?
C6 C10 N11 N12 180.0 . . . . ?
C10 N11 N12 N13 0.0 . . . . ?
Na15 N11 N12 N13 -139.06(6) 6_557 . . . ?
N11 N12 N13 N14 0.0 . . . . ?
N12 N13 N14 C10 0.0 . . . . ?
N11 C10 N14 N13 0.0 . . . . ?
C6 C10 N14 N13 180.0 . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 O8 0.88 1.99 2.524(2) 118.1 .
N1 H1 N12 0.88 2.24 3.026(2) 148.2 1_655
N14 H14 N3 0.88 2.11 2.934(2) 156.5 3_646
N14 H14 O9 0.88 2.01 2.560(2) 119.1 .
O16 H16B N2 0.833(9) 2.029(10) 2.862(2) 179(2) 7_475

_refine_diff_density_max         0.398
_refine_diff_density_min         -0.267
_refine_diff_density_rms         0.068

# start Validation Reply Form
_vrf_PLAT015_shrv434             
;
PROBLEM: No _shelx_hkl_file record in SHELXL20xy CIF ....     Please Do ! 
RESPONSE: It is our policy to routinely not supply the HKL file unless 
specifically required.
;
