# 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_MM
_database_code_depnum_ccdc_archive 'CCDC 1949588'
loop_
_audit_author_name
_audit_author_address
'Shiyu Zhang'
;NUST center
China
;
_audit_update_record             
;
2019-08-27 deposited with the CCDC.	2020-03-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 H4 N14 O4, 2(C2 H6 O S), 4(H2 O)'
_chemical_formula_sum            'C10 H24 N14 O10 S2'
_chemical_formula_weight         564.55

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'

_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                   6.0690(3)
_cell_length_b                   8.3830(6)
_cell_length_c                   12.2268(6)
_cell_angle_alpha                83.361(2)
_cell_angle_beta                 78.909(2)
_cell_angle_gamma                75.168(2)
_cell_volume                     588.65(6)
_cell_formula_units_Z            1
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    3255
_cell_measurement_theta_min      2.52
_cell_measurement_theta_max      26.40

_exptl_crystal_description       disk
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.593
_exptl_crystal_F_000             294
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.070
_exptl_absorpt_coefficient_mu    0.305
_shelx_estimated_absorpt_T_min   0.964
_shelx_estimated_absorpt_T_max   0.979
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.971
_exptl_absorpt_correction_T_max  0.979
_exptl_absorpt_process_details   'Bruker, SADABS'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6546
_diffrn_reflns_av_unetI/netI     0.0357
_diffrn_reflns_av_R_equivalents  0.0292
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.520
_diffrn_reflns_theta_max         26.441
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             2401
_reflns_number_gt                2013
_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 APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_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)+(0.0520P)²+0.5722P] 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         2401
_refine_ls_number_parameters     188
_refine_ls_number_restraints     7
_refine_ls_R_factor_all          0.0572
_refine_ls_R_factor_gt           0.0451
_refine_ls_wR_factor_ref         0.1160
_refine_ls_wR_factor_gt          0.1084
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_restrained_S_all      1.063
_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
S1 S 0.28297(11) 0.15745(7) 0.10383(5) 0.02262(18) Uani 1 1 d . . . . .
O1 O -0.0859(3) 0.8499(2) 0.16781(15) 0.0270(4) Uani 1 1 d . . . . .
O2 O 0.0892(3) 0.5872(2) 0.17394(15) 0.0275(4) Uani 1 1 d . . . . .
O3 O 0.3267(3) 0.2087(2) 0.21138(15) 0.0275(4) Uani 1 1 d . . . . .
O1W O 0.5367(5) 1.0067(3) 0.37951(18) 0.0419(5) Uani 1 1 d D . . . .
O2W O -0.0168(5) 1.0385(3) 0.38675(19) 0.0484(6) Uani 1 1 d D . . . .
N1 N 1.1396(3) 0.3473(2) 0.51922(17) 0.0215(4) Uani 1 1 d . . . . .
N2 N 0.9769(3) 0.3627(2) 0.45828(17) 0.0223(4) Uani 1 1 d . . . . .
N3 N 0.6145(3) 0.4048(2) 0.33627(16) 0.0198(4) Uani 1 1 d . . . . .
N4 N 0.4332(3) 0.4789(2) 0.28340(17) 0.0195(4) Uani 1 1 d . . . . .
N5 N 0.5198(3) 0.6811(2) 0.35129(16) 0.0193(4) Uani 1 1 d D . . . .
N6 N 0.2082(3) 0.7709(2) 0.25652(17) 0.0210(4) Uani 1 1 d . . . . .
N7 N 0.0682(3) 0.7327(2) 0.19837(16) 0.0204(4) Uani 1 1 d . . . . .
C1 C 0.3777(4) 0.6440(3) 0.29246(19) 0.0180(5) Uani 1 1 d D . . . .
C2 C 0.6586(4) 0.5322(3) 0.37508(19) 0.0181(5) Uani 1 1 d D . . . .
C3 C 0.8422(4) 0.5146(3) 0.44078(19) 0.0183(5) Uani 1 1 d . . . . .
C4 C -0.0179(4) 0.2377(3) 0.1025(2) 0.0267(6) Uani 1 1 d . . . . .
H4B H -0.106313 0.176281 0.160099 0.040 Uiso 1 1 calc R U . . .
H4C H -0.051814 0.225975 0.029093 0.040 Uiso 1 1 calc R U . . .
H4D H -0.061155 0.354875 0.117728 0.040 Uiso 1 1 calc R U . . .
C5 C 0.3866(5) 0.2943(3) -0.0048(2) 0.0297(6) Uani 1 1 d . . . . .
H5A H 0.319074 0.408912 0.014622 0.045 Uiso 1 1 calc R U . . .
H5B H 0.342200 0.277929 -0.074822 0.045 Uiso 1 1 calc R U . . .
H5C H 0.555477 0.271483 -0.013815 0.045 Uiso 1 1 calc R U . . .
H1 H 0.537(18) 0.7722(18) 0.360(12) 0.50(11) Uiso 1 1 d D . . . .
H1A H 0.44(4) 1.07(3) 0.35(2) 0.756 Uiso 1 1 d D U . . .
H1B H 0.675(4) 1.017(8) 0.371(6) 0.15(3) Uiso 1 1 d D . . . .
H2A H 0.061(6) 0.965(4) 0.338(3) 0.060(12) Uiso 1 1 d D . . . .
H2B H -0.007(9) 1.141(3) 0.375(4) 0.097(17) Uiso 1 1 d D . . . .
H4 H 0.371(5) 0.429(3) 0.251(2) 0.019(7) Uiso 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O3 1.5190(18) . ?
S1 C4 1.779(3) . ?
S1 C5 1.781(3) . ?
O1 N7 1.248(3) . ?
O2 N7 1.258(3) . ?
O1W H1A 0.840(10) . ?
O1W H1B 0.851(10) . ?
O2W H2A 0.883(19) . ?
O2W H2B 0.869(19) . ?
N1 N2 1.320(3) . ?
N1 C3 1.345(3) 2_766 ?
N2 C3 1.345(3) . ?
N3 C2 1.323(3) . ?
N3 N4 1.359(3) . ?
N4 C1 1.350(3) . ?
N4 H4 0.81(3) . ?
N5 C1 1.336(3) . ?
N5 C2 1.351(3) . ?
N5 H1 0.819(10) . ?
N6 N7 1.324(3) . ?
N6 C1 1.374(3) . ?
C2 C3 1.463(3) . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C4 H4D 0.9800 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 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
O3 S1 C4 105.74(11) . . ?
O3 S1 C5 105.86(11) . . ?
C4 S1 C5 97.70(13) . . ?
H1A O1W H1B 123(10) . . ?
H2A O2W H2B 120(4) . . ?
N2 N1 C3 117.3(2) . 2_766 ?
N1 N2 C3 117.8(2) . . ?
C2 N3 N4 102.07(19) . . ?
C1 N4 N3 110.36(19) . . ?
C1 N4 H4 126.0(19) . . ?
N3 N4 H4 123.6(19) . . ?
C1 N5 C2 103.17(19) . . ?
C1 N5 H1 129(2) . . ?
C2 N5 H1 127(2) . . ?
N7 N6 C1 117.48(19) . . ?
O1 N7 O2 121.39(19) . . ?
O1 N7 N6 116.24(19) . . ?
O2 N7 N6 122.37(19) . . ?
N5 C1 N4 109.0(2) . . ?
N5 C1 N6 118.0(2) . . ?
N4 C1 N6 132.9(2) . . ?
N3 C2 N5 115.4(2) . . ?
N3 C2 C3 122.9(2) . . ?
N5 C2 C3 121.7(2) . . ?
N1 C3 N2 124.9(2) 2_766 . ?
N1 C3 C2 117.0(2) 2_766 . ?
N2 C3 C2 118.1(2) . . ?
S1 C4 H4B 109.5 . . ?
S1 C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
S1 C4 H4D 109.5 . . ?
H4B C4 H4D 109.5 . . ?
H4C C4 H4D 109.5 . . ?
S1 C5 H5A 109.5 . . ?
S1 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
S1 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?

_refine_diff_density_max         0.575
_refine_diff_density_min         -0.319
_refine_diff_density_rms         0.066

####################################################################### 
# 
# 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_22019181_0m
_database_code_depnum_ccdc_archive 'CCDC 1949594'
loop_
_audit_author_name
_audit_author_address
'Shiyu Zhang'
;NUST center
China
;
_audit_update_record             
;
2019-08-27 deposited with the CCDC.	2020-03-18 downloaded from the CCDC.
;
_audit_creation_date             2019-03-01
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C6 H6 N14 O4, 6(C H4 O)'
_chemical_formula_sum            'C12 H30 N14 O10'
_chemical_formula_weight         530.50
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   7.5426(8)
_cell_length_b                   7.2253(8)
_cell_length_c                   21.790(2)
_cell_angle_alpha                90
_cell_angle_beta                 92.711(3)
_cell_angle_gamma                90
_cell_volume                     1186.2(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3607
_cell_measurement_temperature    170
_cell_measurement_theta_max      26.149
_cell_measurement_theta_min      2.704
_shelx_estimated_absorpt_T_max   0.996
_shelx_estimated_absorpt_T_min   0.990
_exptl_absorpt_coefficient_mu    0.127
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6695
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1158 before and 0.0642 after correction. The Ratio of minimum to maximum transmission is 0.8979. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.485
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.03
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0591
_diffrn_reflns_av_unetI/netI     0.0474
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            13596
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.525
_diffrn_reflns_theta_min         2.703
_diffrn_ambient_temperature      170.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1747
_reflns_number_total             2715
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.256
_refine_diff_density_min         -0.540
_refine_diff_density_rms         0.066
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     176
_refine_ls_number_reflns         2715
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1053
_refine_ls_R_factor_gt           0.0608
_refine_ls_restrained_S_all      1.071
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0921P)²+0.8476P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1585
_refine_ls_wR_factor_ref         0.1992
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N5(H5), N6(H6)
2.b Idealised Me refined as rotating group:
 C3(H3A,H3B,H3C), C2(H2A,H2B,H2C), C1(H1A,H1B,H1C)
2.c Idealised tetrahedral OH refined as rotating group:
 O1(H1), O2(H2)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
O4 O 0.1758(3) 0.4768(3) 0.55426(9) 0.0439(5) Uani 1 1 d . . . . .
O5 O 0.1549(3) 0.3318(3) 0.43073(10) 0.0494(6) Uani 1 1 d . . . . .
O3 O 0.1933(3) 0.5672(3) 0.64931(10) 0.0542(6) Uani 1 1 d . . . . .
O1 O 0.8011(3) 0.2021(4) 0.68527(10) 0.0568(6) Uani 1 1 d . . . . .
H1 H 0.738270 0.132446 0.706171 0.085 Uiso 1 1 calc GR . . . .
N5 N 0.6484(3) 0.2434(3) 0.57528(11) 0.0384(6) Uani 1 1 d . . . . .
H5 H 0.716230 0.238990 0.609227 0.046 Uiso 1 1 calc R . . . .
N3 N 0.4330(3) 0.2939(3) 0.50976(11) 0.0374(6) Uani 1 1 d . . . . .
N4 N 0.5576(3) 0.2006(3) 0.47823(11) 0.0386(6) Uani 1 1 d . . . . .
N7 N 0.9781(3) 0.0876(3) 0.55439(11) 0.0405(6) Uani 1 1 d . . . . .
N2 N 0.4156(3) 0.4044(3) 0.61675(11) 0.0414(6) Uani 1 1 d . . . . .
N1 N 0.2567(3) 0.4843(3) 0.60571(11) 0.0411(6) Uani 1 1 d . . . . .
N6 N 0.8705(3) -0.0047(3) 0.45434(11) 0.0423(6) Uani 1 1 d . . . . .
H6 H 0.783737 -0.004887 0.425893 0.051 Uiso 1 1 calc R . . . .
O2 O 0.5924(4) -0.0445(4) 0.73820(11) 0.0702(8) Uani 1 1 d . . . . .
H2 H 0.589164 -0.042082 0.776674 0.105 Uiso 1 1 calc GR . . . .
C4 C 0.4858(3) 0.3207(4) 0.56851(13) 0.0357(6) Uani 1 1 d . . . . .
C5 C 0.6871(3) 0.1736(4) 0.51955(13) 0.0362(6) Uani 1 1 d . . . . .
C6 C 0.8535(3) 0.0802(4) 0.50830(13) 0.0374(6) Uani 1 1 d . . . . .
C3 C 0.2026(5) 0.2888(5) 0.36981(15) 0.0531(8) Uani 1 1 d . . . . .
H3A H 0.211745 0.403444 0.346133 0.080 Uiso 1 1 calc GR . . . .
H3B H 0.111693 0.208806 0.350138 0.080 Uiso 1 1 calc GR . . . .
H3C H 0.317214 0.224650 0.371297 0.080 Uiso 1 1 calc GR . . . .
C2 C 0.9806(5) 0.1820(5) 0.70480(17) 0.0604(9) Uani 1 1 d . . . . .
H2A H 1.042766 0.299657 0.699474 0.091 Uiso 1 1 calc GR . . . .
H2B H 1.035517 0.085918 0.680260 0.091 Uiso 1 1 calc GR . . . .
H2C H 0.988644 0.146540 0.748247 0.091 Uiso 1 1 calc GR . . . .
C1 C 0.4186(5) -0.0315(6) 0.7120(2) 0.0689(10) Uani 1 1 d . . . . .
H1A H 0.421423 -0.045035 0.667262 0.103 Uiso 1 1 calc GR . . . .
H1B H 0.368319 0.089426 0.721791 0.103 Uiso 1 1 calc GR . . . .
H1C H 0.345146 -0.129688 0.728547 0.103 Uiso 1 1 calc GR . . . .
H5A H 0.054(5) 0.384(5) 0.4306(17) 0.061(11) Uiso 1 1 d . . . . .
H3 H 0.344(5) 0.309(5) 0.4917(17) 0.049(10) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O4 N1 1.252(3) . ?
O5 C3 1.426(4) . ?
O5 H5A 0.85(4) . ?
O3 N1 1.238(3) . ?
O1 H1 0.8400 . ?
O1 C2 1.408(4) . ?
N5 H5 0.8800 . ?
N5 C4 1.349(3) . ?
N5 C5 1.359(4) . ?
N3 N4 1.367(3) . ?
N3 C4 1.336(4) . ?
N3 H3 0.77(4) . ?
N4 C5 1.312(3) . ?
N7 N6 1.311(3) 3_756 ?
N7 C6 1.344(3) . ?
N2 N1 1.341(3) . ?
N2 C4 1.343(4) . ?
N6 H6 0.8800 . ?
N6 C6 1.338(4) . ?
O2 H2 0.8400 . ?
O2 C1 1.408(4) . ?
C5 C6 1.456(4) . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 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
C3 O5 H5A 111(3) . . ?
C2 O1 H1 109.5 . . ?
C4 N5 H5 126.6 . . ?
C4 N5 C5 106.8(2) . . ?
C5 N5 H5 126.6 . . ?
N4 N3 H3 115(3) . . ?
C4 N3 N4 111.9(2) . . ?
C4 N3 H3 133(3) . . ?
C5 N4 N3 103.6(2) . . ?
N6 N7 C6 117.2(2) 3_756 . ?
N1 N2 C4 115.8(2) . . ?
O4 N1 N2 122.4(2) . . ?
O3 N1 O4 121.2(2) . . ?
O3 N1 N2 116.4(2) . . ?
N7 N6 H6 121.4 3_756 . ?
N7 N6 C6 117.2(2) 3_756 . ?
C6 N6 H6 121.4 . . ?
C1 O2 H2 109.5 . . ?
N3 C4 N5 105.8(2) . . ?
N3 C4 N2 134.8(3) . . ?
N2 C4 N5 119.4(2) . . ?
N5 C5 C6 123.1(2) . . ?
N4 C5 N5 111.9(2) . . ?
N4 C5 C6 125.0(3) . . ?
N7 C6 C5 115.7(3) . . ?
N6 C6 N7 125.6(3) . . ?
N6 C6 C5 118.7(2) . . ?
O5 C3 H3A 109.5 . . ?
O5 C3 H3B 109.5 . . ?
O5 C3 H3C 109.5 . . ?
H3A C3 H3B 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
O1 C2 H2A 109.5 . . ?
O1 C2 H2B 109.5 . . ?
O1 C2 H2C 109.5 . . ?
H2A C2 H2B 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
O2 C1 H1A 109.5 . . ?
O2 C1 H1B 109.5 . . ?
O2 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
