# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2020

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

data_1
_database_code_depnum_ccdc_archive 'CCDC 1858871'
loop_
_audit_author_name
_audit_author_address
'Jinchao Ma'
;Nanjing University of Science and Technology
China
;
_audit_update_record             
;
2018-07-28 deposited with the CCDC.	2020-03-06 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT430_1                   
;
PROBLEM: Short Inter D...A Contact  O2A      ..N3               2.82 Ang.  
RESPONSE: There is no H-bonding between the two atoms
but dipole-dipole interation.
;
# end Validation Reply Form

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C8 H2 N12 O6'
_chemical_formula_sum            'C8 H2 N12 O6'
_chemical_formula_weight         362.22

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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

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

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

_cell_length_a                   7.6311(9)
_cell_length_b                   9.9671(11)
_cell_length_c                   16.9752(17)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1291.1(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    1399
_cell_measurement_theta_min      3.57
_cell_measurement_theta_max      24.92

_exptl_crystal_description       plate
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.863
_exptl_crystal_F_000             728
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.270
_exptl_crystal_size_min          0.070
_exptl_absorpt_coefficient_mu    0.162
_shelx_estimated_absorpt_T_min   0.953
_shelx_estimated_absorpt_T_max   0.989
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5933
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_process_details   'SADABS (Bruker, 2014)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'PHOTON 100 CMOS detector'
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5766
_diffrn_reflns_av_unetI/netI     0.0465
_diffrn_reflns_av_R_equivalents  0.0714
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.570
_diffrn_reflns_theta_max         25.349
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             1173
_reflns_number_gt                824
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0456P)²+1.2885P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1173
_refine_ls_number_parameters     140
_refine_ls_number_restraints     27
_refine_ls_R_factor_all          0.0846
_refine_ls_R_factor_gt           0.0474
_refine_ls_wR_factor_ref         0.1148
_refine_ls_wR_factor_gt          0.0984
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_restrained_S_all      1.022
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.0723(3) 0.5375(3) 0.01768(16) 0.0207(6) Uani 1 1 d . . . . .
C2 C 0.3060(3) 0.5826(3) 0.07692(16) 0.0201(6) Uani 1 1 d . . . . .
C3 C 0.5627(4) 0.6353(3) 0.17773(17) 0.0267(7) Uani 1 1 d D . . . .
C4 C 0.4757(3) 0.5665(3) 0.11618(16) 0.0226(7) Uani 1 1 d . . . . .
N1 N 0.2287(3) 0.6966(2) 0.05529(14) 0.0225(6) Uani 1 1 d . . . . .
H1 H 0.262(4) 0.775(3) 0.0584(17) 0.027 Uiso 1 1 d . U . . .
N2 N 0.0785(3) 0.6709(2) 0.01648(14) 0.0233(6) Uani 1 1 d . . . . .
N3 N 0.2104(3) 0.4780(2) 0.05366(13) 0.0207(5) Uani 1 1 d . . . . .
N4 N 0.7089(3) 0.5779(3) 0.19616(15) 0.0380(7) Uani 1 1 d . . . . .
N5 N 0.5737(3) 0.4644(3) 0.09724(15) 0.0335(7) Uani 1 1 d . . . . .
O1 O 0.7189(3) 0.4710(2) 0.14596(14) 0.0433(6) Uani 1 1 d . . . . .
N6 N 0.5122(3) 0.7550(3) 0.21916(16) 0.0358(7) Uani 1 1 d D . . . .
O2A O 0.4235(18) 0.8345(10) 0.1834(6) 0.041(3) Uani 0.67(10) 1 d D U P A 1
O3A O 0.561(2) 0.7678(13) 0.2867(6) 0.070(3) Uani 0.67(10) 1 d D U P A 1
O2Z O 0.398(6) 0.823(4) 0.190(2) 0.073(9) Uani 0.33(10) 1 d D U P A 2
O3Z O 0.585(5) 0.781(3) 0.2805(16) 0.100(9) Uani 0.33(10) 1 d D U P A 2


_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 N2 1.331(3) . ?
C1 N3 1.355(3) . ?
C1 C1 1.461(5) 5_565 ?
C2 N3 1.332(3) . ?
C2 N1 1.332(3) . ?
C2 C4 1.466(4) . ?
C3 N4 1.292(4) . ?
C3 C4 1.415(4) . ?
C3 N6 1.438(4) . ?
C4 N5 1.303(3) . ?
N1 N2 1.347(3) . ?
N1 H1 0.83(3) . ?
N4 O1 1.367(3) . ?
N5 O1 1.384(3) . ?
N6 O2A 1.206(7) . ?
N6 O2Z 1.211(11) . ?
N6 O3Z 1.206(11) . ?
N6 O3A 1.213(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
N2 C1 N3 114.6(2) . . ?
N2 C1 C1 122.1(3) . 5_565 ?
N3 C1 C1 123.3(3) . 5_565 ?
N3 C2 N1 110.1(2) . . ?
N3 C2 C4 122.2(2) . . ?
N1 C2 C4 127.6(2) . . ?
N4 C3 C4 111.7(3) . . ?
N4 C3 N6 118.7(3) . . ?
C4 C3 N6 129.6(3) . . ?
N5 C4 C3 107.0(2) . . ?
N5 C4 C2 118.7(2) . . ?
C3 C4 C2 134.2(3) . . ?
C2 N1 N2 110.4(2) . . ?
C2 N1 H1 131(2) . . ?
N2 N1 H1 118(2) . . ?
C1 N2 N1 102.3(2) . . ?
C2 N3 C1 102.5(2) . . ?
C3 N4 O1 104.1(2) . . ?
C4 N5 O1 105.9(2) . . ?
N4 O1 N5 111.4(2) . . ?
O2Z N6 O3Z 124.8(11) . . ?
O2A N6 O3A 125.5(5) . . ?
O2A N6 C3 116.7(5) . . ?
O2Z N6 C3 116.8(10) . . ?
O3Z N6 C3 118.4(10) . . ?
O3A N6 C3 117.8(4) . . ?

_refine_diff_density_max         0.275
_refine_diff_density_min         -0.242
_refine_diff_density_rms         0.062

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

data_1_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1860198'
loop_
_audit_author_name
_audit_author_address
'Jinchao Ma'
;Nanjing University of Science and Technology
China
;
_audit_update_record             
;
2018-08-04 deposited with the CCDC.	2020-03-06 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         
'C12 H14 N12 O4 S2, 0.67(C2 H6 O S), 0.82(H2 O)'
_chemical_formula_sum            'C13.33 H19.64 N12 O5.49 S2.67'
_chemical_formula_weight         521.30

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

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

_cell_length_a                   5.2901(3)
_cell_length_b                   18.3313(11)
_cell_length_c                   33.371(2)
_cell_angle_alpha                90
_cell_angle_beta                 92.366(2)
_cell_angle_gamma                90
_cell_volume                     3233.3(3)
_cell_formula_units_Z            6
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    5161
_cell_measurement_theta_min      3.05
_cell_measurement_theta_max      25.08

_exptl_crystal_description       plate
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.606
_exptl_crystal_F_000             1621
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.360
_exptl_crystal_size_mid          0.290
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.371
_shelx_estimated_absorpt_T_min   0.878
_shelx_estimated_absorpt_T_max   0.957
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6060
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_process_details   'SADABS (Bruker, 2014)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'PHOTON 100 CMOS detector'
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            18271
_diffrn_reflns_av_unetI/netI     0.0785
_diffrn_reflns_av_R_equivalents  0.0679
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_limit_l_max       40
_diffrn_reflns_theta_min         3.251
_diffrn_reflns_theta_max         25.353
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measured_fraction_theta_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_point_group_measured_fraction_full 0.990
_reflns_number_total             5862
_reflns_number_gt                3951
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0410P)²+7.7994P] 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         5862
_refine_ls_number_parameters     517
_refine_ls_number_restraints     187
_refine_ls_R_factor_all          0.1150
_refine_ls_R_factor_gt           0.0670
_refine_ls_wR_factor_ref         0.1421
_refine_ls_wR_factor_gt          0.1259
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_restrained_S_all      1.041
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.7362(8) 0.1538(2) 0.17990(12) 0.0223(9) Uani 1 1 d . . . . .
C2 C 1.0413(8) 0.1900(2) 0.21619(12) 0.0234(9) Uani 1 1 d . . . . .
C3 C 0.5407(7) 0.1114(2) 0.15774(12) 0.0212(9) Uani 1 1 d . . . . .
C4 C 0.2317(7) 0.0878(2) 0.11906(12) 0.0189(9) Uani 1 1 d . . . . .
C5 C 1.3978(7) 0.2510(2) 0.26189(12) 0.0255(10) Uani 1 1 d . . . . .
C6 C 1.2593(8) 0.1899(2) 0.24471(12) 0.0247(10) Uani 1 1 d . . . . .
C7 C 1.3873(10) 0.4640(3) 0.25675(16) 0.0467(14) Uani 1 1 d . . . . .
H7A H 1.2049 0.4687 0.2510 0.070 Uiso 1 1 calc R U . . .
H7B H 1.4758 0.4632 0.2315 0.070 Uiso 1 1 calc R U . . .
H7C H 1.4471 0.5055 0.2730 0.070 Uiso 1 1 calc R U . . .
C8 C 1.7792(8) 0.3821(3) 0.29103(17) 0.0465(14) Uani 1 1 d . . . . .
H8A H 1.8337 0.4278 0.3039 0.070 Uiso 1 1 calc R U . . .
H8B H 1.8594 0.3773 0.2652 0.070 Uiso 1 1 calc R U . . .
H8C H 1.8289 0.3409 0.3083 0.070 Uiso 1 1 calc R U . . .
C9 C -0.1348(7) 0.0286(2) 0.07677(12) 0.0212(9) Uani 1 1 d . . . . .
C10 C 0.0169(7) 0.0890(2) 0.09020(12) 0.0197(9) Uani 1 1 d . . . . .
C11 C -0.2348(9) -0.1135(3) 0.02054(13) 0.0383(12) Uani 1 1 d . . . . .
H11A H -0.3112 -0.1597 0.0116 0.057 Uiso 1 1 calc R U . . .
H11B H -0.0576 -0.1120 0.0131 0.057 Uiso 1 1 calc R U . . .
H11C H -0.3272 -0.0728 0.0077 0.057 Uiso 1 1 calc R U . . .
C12 C -0.0796(8) -0.1809(2) 0.09147(13) 0.0267(10) Uani 1 1 d . . . . .
H12A H -0.0696 -0.1791 0.1208 0.040 Uiso 1 1 calc R U . . .
H12B H 0.0915 -0.1798 0.0813 0.040 Uiso 1 1 calc R U . . .
H12C H -0.1646 -0.2260 0.0827 0.040 Uiso 1 1 calc R U . . .
C13 C -0.3896(7) 0.5164(2) 0.01073(13) 0.0265(10) Uani 1 1 d . . . . .
C14 C -0.0985(8) 0.5885(2) 0.02702(13) 0.0247(10) Uani 1 1 d . . . . .
C15 C 0.2912(8) 0.6565(2) 0.05820(13) 0.0234(10) Uani 1 1 d . . . . .
C16 C 0.0813(7) 0.6482(2) 0.03000(12) 0.0229(10) Uani 1 1 d . . . . .
C17 C 0.3967(9) 0.7056(3) 0.14794(15) 0.0412(13) Uani 1 1 d . . . . .
H17A H 0.4835 0.7126 0.1742 0.062 Uiso 1 1 calc R U . . .
H17B H 0.2165 0.6966 0.1516 0.062 Uiso 1 1 calc R U . . .
H17C H 0.4162 0.7495 0.1316 0.062 Uiso 1 1 calc R U . . .
C18 C 0.4968(15) 0.5573(3) 0.15678(18) 0.081(2) Uani 1 1 d . . . . .
H18A H 0.5774 0.5139 0.1459 0.121 Uiso 1 1 calc R U . . .
H18B H 0.3168 0.5475 0.1602 0.121 Uiso 1 1 calc R U . . .
H18C H 0.5782 0.5696 0.1828 0.121 Uiso 1 1 calc R U . . .
N1 N 0.9420(7) 0.2513(2) 0.20145(10) 0.0291(9) Uani 1 1 d . . . . .
N2 N 0.7459(7) 0.2261(2) 0.17800(11) 0.0285(9) Uani 1 1 d D . . . .
H2 H 0.654(7) 0.2575(19) 0.1652(12) 0.034 Uiso 1 1 d D U . . .
N3 N 0.9201(6) 0.12795(18) 0.20394(10) 0.0245(8) Uani 1 1 d . . . . .
N4 N 0.3161(6) 0.02595(18) 0.13661(11) 0.0255(8) Uani 1 1 d D . . . .
H4 H 0.259(8) -0.0167(13) 0.1350(13) 0.031 Uiso 1 1 d D U . . .
N5 N 0.5168(6) 0.04009(19) 0.16191(11) 0.0287(9) Uani 1 1 d . . . . .
N6 N 0.3711(6) 0.14381(17) 0.13193(10) 0.0215(8) Uani 1 1 d . . . . .
N7 N 1.5756(7) 0.2254(2) 0.28659(11) 0.0322(9) Uani 1 1 d . . . . .
N8 N 1.3520(7) 0.1299(2) 0.25920(11) 0.0348(9) Uani 1 1 d . . . . .
N9 N 1.3486(7) 0.32334(19) 0.25305(11) 0.0288(9) Uani 1 1 d . . . . .
N10 N -0.3116(6) 0.05223(19) 0.05136(11) 0.0278(9) Uani 1 1 d . . . . .
N11 N -0.0655(7) 0.14860(19) 0.07310(11) 0.0303(9) Uani 1 1 d . . . . .
N12 N -0.0875(6) -0.04155(18) 0.08929(10) 0.0228(8) Uani 1 1 d . . . . .
N13 N -0.0856(7) 0.5313(2) 0.05115(12) 0.0362(10) Uani 1 1 d D . . . .
H13 H 0.013(8) 0.519(3) 0.0706(10) 0.043 Uiso 1 1 d D U . . .
N14 N -0.2718(7) 0.4830(2) 0.04126(12) 0.0359(10) Uani 1 1 d . . . . .
N15 N -0.2892(6) 0.58085(19) 0.00019(10) 0.0270(9) Uani 1 1 d . . . . .
N16 N 0.4071(6) 0.71769(19) 0.05095(10) 0.0271(8) Uani 1 1 d . . . . .
N17 N 0.0701(7) 0.7044(2) 0.00646(12) 0.0373(10) Uani 1 1 d . . . . .
N18 N 0.3532(6) 0.6062(2) 0.08751(11) 0.0310(9) Uani 1 1 d . . . . .
O1 O 1.5489(6) 0.14936(17) 0.28512(10) 0.0382(8) Uani 1 1 d . . . . .
O2 O 1.3403(6) 0.38427(17) 0.32243(9) 0.0354(8) Uani 1 1 d . . . . .
O3 O -0.2691(6) 0.12770(16) 0.04868(9) 0.0349(8) Uani 1 1 d . . . . .
O4 O -0.5104(5) -0.11057(18) 0.08363(11) 0.0464(9) Uani 1 1 d . . . . .
O5 O 0.2684(6) 0.74902(17) 0.01861(9) 0.0377(8) Uani 1 1 d . . . . .
O6 O 0.7903(6) 0.64660(18) 0.11772(10) 0.0434(9) Uani 1 1 d . . . . .
O8 O 0.8966(10) 0.4138(2) 0.19050(13) 0.0857(15) Uani 1 1 d D . . . .
H8D H 0.7353 0.4005 0.1896 0.103 Uiso 1 1 d DR U . . .
H8E H 0.9739 0.3761 0.1982 0.103 Uiso 1 1 d DR U . . .
S1 S 1.4483(2) 0.38263(6) 0.28317(3) 0.0285(3) Uani 1 1 d . . . . .
S2 S -0.25002(18) -0.10622(6) 0.07297(3) 0.0225(3) Uani 1 1 d . . . . .
S3 S 0.5289(2) 0.63048(6) 0.12364(4) 0.0336(3) Uani 1 1 d . . . . .
O7A O 0.522(3) 0.3504(8) 0.1416(4) 0.063(4) Uani 0.554(4) 1 d D U P A 1
S4A S 0.4001(5) 0.36598(13) 0.10066(7) 0.0431(9) Uani 0.554(4) 1 d D U P A 1
C19A C 0.520(2) 0.2978(8) 0.0684(4) 0.054(4) Uani 0.554(4) 1 d D U P A 1
H19A H 0.7017 0.3054 0.0655 0.082 Uiso 0.554(4) 1 calc R U P A 1
H19B H 0.4323 0.3010 0.0420 0.082 Uiso 0.554(4) 1 calc R U P A 1
H19C H 0.4917 0.2494 0.0799 0.082 Uiso 0.554(4) 1 calc R U P A 1
C20A C 0.0885(17) 0.3326(6) 0.1009(3) 0.065(3) Uani 0.554(4) 1 d D U P A 1
H20A H 0.0895 0.2831 0.1120 0.097 Uiso 0.554(4) 1 calc R U P A 1
H20B H 0.0156 0.3318 0.0735 0.097 Uiso 0.554(4) 1 calc R U P A 1
H20C H -0.0133 0.3644 0.1175 0.097 Uiso 0.554(4) 1 calc R U P A 1
O7Z O 0.494(3) 0.3288(9) 0.1445(4) 0.055(4) Uani 0.446(4) 1 d D U P A 2
S4Z S 0.2750(6) 0.31495(15) 0.11409(8) 0.0383(11) Uani 0.446(4) 1 d D U P A 2
C19Z C 0.415(3) 0.2869(9) 0.0693(4) 0.044(4) Uani 0.446(4) 1 d D U P A 2
H19D H 0.5368 0.3238 0.0612 0.066 Uiso 0.446(4) 1 calc R U P A 2
H19E H 0.2832 0.2810 0.0480 0.066 Uiso 0.446(4) 1 calc R U P A 2
H19F H 0.5023 0.2403 0.0738 0.066 Uiso 0.446(4) 1 calc R U P A 2
C20Z C 0.185(2) 0.4038(6) 0.0976(4) 0.051(3) Uani 0.446(4) 1 d D U P A 2
H20D H 0.1070 0.4299 0.1196 0.076 Uiso 0.446(4) 1 calc R U P A 2
H20E H 0.0627 0.3999 0.0748 0.076 Uiso 0.446(4) 1 calc R U P A 2
H20F H 0.3345 0.4305 0.0894 0.076 Uiso 0.446(4) 1 calc R U P A 2
O9 O 0.029(3) 0.5049(9) 0.1416(5) 0.058(7) Uani 0.228(11) 1 d . . P . .
H9C H -0.0584 0.5433 0.1380 0.070 Uiso 0.228(11) 1 d R U P . .
H9D H -0.0380 0.4788 0.1594 0.070 Uiso 0.228(11) 1 d R U P . .


_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 N3 1.323(5) . ?
C1 N2 1.328(5) . ?
C1 C3 1.469(5) . ?
C2 N1 1.327(5) . ?
C2 N3 1.359(5) . ?
C2 C6 1.465(6) . ?
C3 N5 1.321(5) . ?
C3 N6 1.355(5) . ?
C4 N6 1.325(5) . ?
C4 N4 1.344(5) . ?
C4 C10 1.459(5) . ?
C5 N7 1.311(5) . ?
C5 N9 1.381(5) . ?
C5 C6 1.443(6) . ?
C6 N8 1.290(6) . ?
C7 S1 1.756(5) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 S1 1.759(4) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 N10 1.309(5) . ?
C9 N12 1.373(5) . ?
C9 C10 1.428(5) . ?
C10 N11 1.299(5) . ?
C11 S2 1.760(5) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 S2 1.739(4) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 N14 1.322(6) . ?
C13 N15 1.349(5) . ?
C13 C13 1.473(8) 3_465 ?
C14 N13 1.322(6) . ?
C14 N15 1.328(5) . ?
C14 C16 1.451(6) . ?
C15 N16 1.306(5) . ?
C15 N18 1.374(5) . ?
C15 C16 1.434(6) . ?
C16 N17 1.294(5) . ?
C17 S3 1.757(5) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 S3 1.751(5) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
N1 N2 1.355(5) . ?
N2 H2 0.857(19) . ?
N4 N5 1.354(5) . ?
N4 H4 0.839(19) . ?
N7 O1 1.402(5) . ?
N8 O1 1.373(4) . ?
N9 S1 1.558(4) . ?
N10 O3 1.405(4) . ?
N11 O3 1.378(4) . ?
N12 S2 1.550(3) . ?
N13 N14 1.355(5) . ?
N13 H13 0.847(19) . ?
N16 O5 1.403(4) . ?
N17 O5 1.379(4) . ?
N18 S3 1.557(4) . ?
O2 S1 1.451(3) . ?
O4 S2 1.439(3) . ?
O6 S3 1.436(3) . ?
O8 H8D 0.8869 . ?
O8 H8E 0.8375 . ?
O7A S4A 1.514(9) . ?
S4A C20A 1.758(9) . ?
S4A C19A 1.784(9) . ?
C19A H19A 0.9800 . ?
C19A H19B 0.9800 . ?
C19A H19C 0.9800 . ?
C20A H20A 0.9800 . ?
C20A H20B 0.9800 . ?
C20A H20C 0.9800 . ?
O7Z S4Z 1.530(11) . ?
S4Z C19Z 1.772(11) . ?
S4Z C20Z 1.777(9) . ?
C19Z H19D 0.9800 . ?
C19Z H19E 0.9800 . ?
C19Z H19F 0.9800 . ?
C20Z H20D 0.9800 . ?
C20Z H20E 0.9800 . ?
C20Z H20F 0.9800 . ?
O9 H9C 0.8501 . ?
O9 H9D 0.8500 . ?

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
N3 C1 N2 111.0(3) . . ?
N3 C1 C3 126.9(4) . . ?
N2 C1 C3 122.1(4) . . ?
N1 C2 N3 115.0(4) . . ?
N1 C2 C6 122.0(4) . . ?
N3 C2 C6 123.0(4) . . ?
N5 C3 N6 115.9(3) . . ?
N5 C3 C1 122.6(4) . . ?
N6 C3 C1 121.5(4) . . ?
N6 C4 N4 110.0(3) . . ?
N6 C4 C10 127.6(4) . . ?
N4 C4 C10 122.4(3) . . ?
N7 C5 N9 127.0(4) . . ?
N7 C5 C6 108.2(4) . . ?
N9 C5 C6 124.9(4) . . ?
N8 C6 C5 109.5(4) . . ?
N8 C6 C2 121.4(4) . . ?
C5 C6 C2 129.1(4) . . ?
S1 C7 H7A 109.5 . . ?
S1 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
S1 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
S1 C8 H8A 109.5 . . ?
S1 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
S1 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N10 C9 N12 128.5(4) . . ?
N10 C9 C10 108.9(4) . . ?
N12 C9 C10 122.5(3) . . ?
N11 C10 C9 109.8(4) . . ?
N11 C10 C4 122.8(4) . . ?
C9 C10 C4 127.4(4) . . ?
S2 C11 H11A 109.5 . . ?
S2 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
S2 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
S2 C12 H12A 109.5 . . ?
S2 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
S2 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N14 C13 N15 115.4(4) . . ?
N14 C13 C13 121.7(5) . 3_465 ?
N15 C13 C13 122.9(5) . 3_465 ?
N13 C14 N15 110.2(4) . . ?
N13 C14 C16 122.7(4) . . ?
N15 C14 C16 127.1(4) . . ?
N16 C15 N18 127.4(4) . . ?
N16 C15 C16 109.0(4) . . ?
N18 C15 C16 123.5(4) . . ?
N17 C16 C15 109.2(4) . . ?
N17 C16 C14 123.0(4) . . ?
C15 C16 C14 127.8(4) . . ?
S3 C17 H17A 109.5 . . ?
S3 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
S3 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
S3 C18 H18A 109.5 . . ?
S3 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
S3 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C2 N1 N2 101.9(3) . . ?
C1 N2 N1 110.1(4) . . ?
C1 N2 H2 132(3) . . ?
N1 N2 H2 118(3) . . ?
C1 N3 C2 102.0(3) . . ?
C4 N4 N5 110.4(3) . . ?
C4 N4 H4 130(3) . . ?
N5 N4 H4 119(3) . . ?
C3 N5 N4 101.5(3) . . ?
C4 N6 C3 102.2(3) . . ?
C5 N7 O1 105.3(3) . . ?
C6 N8 O1 106.3(3) . . ?
C5 N9 S1 118.4(3) . . ?
C9 N10 O3 104.7(3) . . ?
C10 N11 O3 105.4(3) . . ?
C9 N12 S2 121.2(3) . . ?
C14 N13 N14 110.6(4) . . ?
C14 N13 H13 134(3) . . ?
N14 N13 H13 116(3) . . ?
C13 N14 N13 101.5(4) . . ?
C14 N15 C13 102.3(4) . . ?
C15 N16 O5 105.0(3) . . ?
C16 N17 O5 106.1(3) . . ?
C15 N18 S3 118.5(3) . . ?
N8 O1 N7 110.7(3) . . ?
N11 O3 N10 111.1(3) . . ?
N17 O5 N16 110.5(3) . . ?
H8D O8 H8E 103.9 . . ?
O2 S1 N9 117.48(19) . . ?
O2 S1 C7 111.4(2) . . ?
N9 S1 C7 102.6(2) . . ?
O2 S1 C8 107.0(2) . . ?
N9 S1 C8 113.6(2) . . ?
C7 S1 C8 103.9(3) . . ?
O4 S2 N12 118.57(19) . . ?
O4 S2 C12 110.9(2) . . ?
N12 S2 C12 101.87(19) . . ?
O4 S2 C11 109.0(2) . . ?
N12 S2 C11 111.1(2) . . ?
C12 S2 C11 104.4(2) . . ?
O6 S3 N18 120.0(2) . . ?
O6 S3 C18 111.3(3) . . ?
N18 S3 C18 101.5(2) . . ?
O6 S3 C17 107.9(2) . . ?
N18 S3 C17 110.2(2) . . ?
C18 S3 C17 104.9(3) . . ?
O7A S4A C20A 107.1(7) . . ?
O7A S4A C19A 105.3(6) . . ?
C20A S4A C19A 96.7(6) . . ?
S4A C19A H19A 109.5 . . ?
S4A C19A H19B 109.5 . . ?
H19A C19A H19B 109.5 . . ?
S4A C19A H19C 109.5 . . ?
H19A C19A H19C 109.5 . . ?
H19B C19A H19C 109.5 . . ?
S4A C20A H20A 109.5 . . ?
S4A C20A H20B 109.5 . . ?
H20A C20A H20B 109.5 . . ?
S4A C20A H20C 109.5 . . ?
H20A C20A H20C 109.5 . . ?
H20B C20A H20C 109.5 . . ?
O7Z S4Z C19Z 106.1(8) . . ?
O7Z S4Z C20Z 103.9(7) . . ?
C19Z S4Z C20Z 97.0(7) . . ?
S4Z C19Z H19D 109.5 . . ?
S4Z C19Z H19E 109.5 . . ?
H19D C19Z H19E 109.5 . . ?
S4Z C19Z H19F 109.5 . . ?
H19D C19Z H19F 109.5 . . ?
H19E C19Z H19F 109.5 . . ?
S4Z C20Z H20D 109.5 . . ?
S4Z C20Z H20E 109.5 . . ?
H20D C20Z H20E 109.5 . . ?
S4Z C20Z H20F 109.5 . . ?
H20D C20Z H20F 109.5 . . ?
H20E C20Z H20F 109.5 . . ?
H9C O9 H9D 108.7 . . ?

_refine_diff_density_max         0.470
_refine_diff_density_min         -0.440
_refine_diff_density_rms         0.074

