# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_mo_20220506_nlg_lcc_22_1_0m
_database_code_depnum_ccdc_archive 'CCDC 2176159'
loop_
_audit_author_name
_audit_author_address
a-b
;Nanjing University of Science and Technology
China
;
_audit_update_record             
;
2022-05-31 deposited with the CCDC.	2022-09-16 downloaded from the CCDC.
;
_audit_creation_date             2022-05-06
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C8 H4 N14 O4, 4(C H4 O)'
_chemical_formula_sum            'C12 H20 N14 O8'
_chemical_formula_weight         488.42
_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                   13.6503(13)
_cell_length_b                   11.5914(17)
_cell_length_c                   6.6234(7)
_cell_angle_alpha                90
_cell_angle_beta                 99.337(4)
_cell_angle_gamma                90
_cell_volume                     1034.1(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1037
_cell_measurement_temperature    193.00
_cell_measurement_theta_max      23.916
_cell_measurement_theta_min      2.318
_shelx_estimated_absorpt_T_max   0.987
_shelx_estimated_absorpt_T_min   0.980
_exptl_absorpt_coefficient_mu    0.132
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6905
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0897 before and 0.0633 after correction.
The Ratio of minimum to maximum transmission is 0.9261.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.569
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             508
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0677
_diffrn_reflns_av_unetI/netI     0.0641
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            8748
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.487
_diffrn_reflns_theta_min         2.318
_diffrn_ambient_temperature      193.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1580
_reflns_number_total             2381
_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 V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_refine_diff_density_max         0.273
_refine_diff_density_min         -0.270
_refine_diff_density_rms         0.063
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     194
_refine_ls_number_reflns         2381
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0823
_refine_ls_R_factor_gt           0.0512
_refine_ls_restrained_S_all      1.047
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0563P)²+0.2190P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1170
_refine_ls_wR_factor_ref         0.1382
_refine_special_details          ?
_olex2_refinement_description    
;
;
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     iterative
_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
O1 O 0.89339(14) 0.70626(18) 1.2957(3) 0.0412(5) Uani 1 1 d . . . A 4
O2 O 0.95086(12) 0.59010(15) 1.0885(3) 0.0285(4) Uani 1 1 d . . . A 4
N1 N 0.51258(14) 0.58733(16) 0.7375(3) 0.0221(4) Uani 1 1 d . . . A 4
N2 N 0.63395(14) 0.50950(16) 0.5794(3) 0.0199(4) Uani 1 1 d . . . A 4
N3 N 0.67329(13) 0.56744(15) 0.7526(3) 0.0179(4) Uani 1 1 d . . . A 4
N4 N 0.61856(14) 0.67564(17) 1.0222(3) 0.0265(5) Uani 1 1 d . . . A 4
N5 N 0.71233(14) 0.68249(17) 1.1066(3) 0.0239(5) Uani 1 1 d . . . A 4
N6 N 0.88210(14) 0.64452(17) 1.1458(3) 0.0232(4) Uani 1 1 d . . . A 4
N7 N 0.83645(16) 0.51726(19) 0.7457(4) 0.0262(5) Uani 1 1 d . . . A 4
H7A H 0.896(2) 0.517(2) 0.809(5) 0.031(8) Uiso 1 1 d . . . B 4
H7B H 0.824(2) 0.485(3) 0.618(5) 0.046(9) Uiso 1 1 d . . . C 4
C1 C 0.53732(16) 0.52511(19) 0.5800(3) 0.0188(5) Uani 1 1 d . . . A 4
C2 C 0.60018(16) 0.61423(19) 0.8456(4) 0.0200(5) Uani 1 1 d . . . A 4
C3 C 0.78395(16) 0.63107(19) 1.0251(3) 0.0198(5) Uani 1 1 d . . . A 4
C4 C 0.77185(16) 0.56972(19) 0.8386(3) 0.0194(5) Uani 1 1 d . . . A 4
O3 O 0.66295(13) 0.39849(15) 1.0969(3) 0.0278(4) Uani 1 1 d . . . D 4
H3 H 0.613(3) 0.404(3) 1.156(6) 0.059(11) Uiso 1 1 d . . . E 4
C6 C 0.6488(3) 0.3053(3) 0.9558(5) 0.0367(7) Uani 1 1 d . . . D 4
H6A H 0.701(3) 0.315(3) 0.872(6) 0.068(11) Uiso 1 1 d . . . F 4
H6B H 0.579(3) 0.308(3) 0.868(6) 0.080(13) Uiso 1 1 d . . . G 4
H6C H 0.651(3) 0.231(4) 1.007(6) 0.073(12) Uiso 1 1 d . . . H 4
O4 O 0.82955(15) 0.42530(18) 1.3661(3) 0.0393(5) Uani 1 1 d . . . I 4
H4 H 0.771(3) 0.418(3) 1.281(6) 0.066(11) Uiso 1 1 d . . . J 4
C5 C 0.9004(3) 0.3445(3) 1.3227(5) 0.0426(7) Uani 1 1 d . . . I 4
H5A H 0.960(3) 0.356(4) 1.415(7) 0.078(13) Uiso 1 1 d . . . K 4
H5B H 0.916(2) 0.358(3) 1.187(6) 0.051(9) Uiso 1 1 d . . . L 4
H5C H 0.879(3) 0.265(4) 1.332(7) 0.086(14) Uiso 1 1 d . . . M 4


_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
O1 N6 1.213(3) . ?
O2 N6 1.240(2) . ?
N1 C1 1.355(3) . ?
N1 C2 1.328(3) . ?
N2 N3 1.363(3) . ?
N2 C1 1.332(3) . ?
N3 C2 1.367(3) . ?
N3 C4 1.373(3) . ?
N4 N5 1.314(3) . ?
N4 C2 1.357(3) . ?
N5 C3 1.332(3) . ?
N6 C3 1.453(3) . ?
N7 H7A 0.85(3) . ?
N7 H7B 0.92(3) . ?
N7 C4 1.304(3) . ?
C1 C1 1.466(5) 3_666 ?
C3 C4 1.412(3) . ?
O3 H3 0.84(4) . ?
O3 C6 1.421(3) . ?
C6 H6A 0.97(4) . ?
C6 H6B 1.03(4) . ?
C6 H6C 0.92(4) . ?
O4 H4 0.90(4) . ?
O4 C5 1.409(3) . ?
C5 H5A 0.95(5) . ?
C5 H5B 0.97(3) . ?
C5 H5C 0.97(5) . ?

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
C2 N1 C1 103.02(18) . . ?
C1 N2 N3 100.69(17) . . ?
N2 N3 C2 110.99(18) . . ?
N2 N3 C4 125.75(17) . . ?
C2 N3 C4 122.91(19) . . ?
N5 N4 C2 115.46(18) . . ?
N4 N5 C3 121.9(2) . . ?
O1 N6 O2 123.3(2) . . ?
O1 N6 C3 119.81(19) . . ?
O2 N6 C3 116.93(18) . . ?
H7A N7 H7B 118(3) . . ?
C4 N7 H7A 115.6(19) . . ?
C4 N7 H7B 126(2) . . ?
N1 C1 C1 122.5(2) . 3_666 ?
N2 C1 N1 116.4(2) . . ?
N2 C1 C1 121.1(2) . 3_666 ?
N1 C2 N3 108.85(19) . . ?
N1 C2 N4 127.78(19) . . ?
N4 C2 N3 123.4(2) . . ?
N5 C3 N6 113.62(19) . . ?
N5 C3 C4 126.2(2) . . ?
C4 C3 N6 120.15(19) . . ?
N3 C4 C3 109.87(18) . . ?
N7 C4 N3 119.2(2) . . ?
N7 C4 C3 130.9(2) . . ?
C6 O3 H3 109(2) . . ?
O3 C6 H6A 105(2) . . ?
O3 C6 H6B 111(2) . . ?
O3 C6 H6C 118(2) . . ?
H6A C6 H6B 112(3) . . ?
H6A C6 H6C 110(3) . . ?
H6B C6 H6C 102(3) . . ?
C5 O4 H4 112(2) . . ?
O4 C5 H5A 109(2) . . ?
O4 C5 H5B 110(2) . . ?
O4 C5 H5C 113(2) . . ?
H5A C5 H5B 106(3) . . ?
H5A C5 H5C 109(4) . . ?
H5B C5 H5C 109(3) . . ?

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
O1 N6 C3 N5 -5.9(3) . . . . ?
O1 N6 C3 C4 173.1(2) . . . . ?
O2 N6 C3 N5 173.63(19) . . . . ?
O2 N6 C3 C4 -7.4(3) . . . . ?
N2 N3 C2 N1 0.5(3) . . . . ?
N2 N3 C2 N4 179.4(2) . . . . ?
N2 N3 C4 N7 3.4(3) . . . . ?
N2 N3 C4 C3 -175.51(19) . . . . ?
N3 N2 C1 N1 0.0(2) . . . . ?
N3 N2 C1 C1 -178.8(3) . . . 3_666 ?
N4 N5 C3 N6 -177.4(2) . . . . ?
N4 N5 C3 C4 3.7(4) . . . . ?
N5 N4 C2 N1 175.0(2) . . . . ?
N5 N4 C2 N3 -3.6(3) . . . . ?
N5 C3 C4 N3 -1.6(3) . . . . ?
N5 C3 C4 N7 179.6(2) . . . . ?
N6 C3 C4 N3 179.54(18) . . . . ?
N6 C3 C4 N7 0.8(4) . . . . ?
C1 N1 C2 N3 -0.5(2) . . . . ?
C1 N1 C2 N4 -179.3(2) . . . . ?
C1 N2 N3 C2 -0.3(2) . . . . ?
C1 N2 N3 C4 173.0(2) . . . . ?
C2 N1 C1 N2 0.3(3) . . . . ?
C2 N1 C1 C1 179.1(3) . . . 3_666 ?
C2 N3 C4 N7 176.0(2) . . . . ?
C2 N3 C4 C3 -2.9(3) . . . . ?
C2 N4 N5 C3 -0.9(3) . . . . ?
C4 N3 C2 N1 -173.03(19) . . . . ?
C4 N3 C2 N4 5.8(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_cu_20220407_nlg_lcc_22_1_0m
_database_code_depnum_ccdc_archive 'CCDC 2176161'
loop_
_audit_author_name
_audit_author_address
a-b
;Nanjing University of Science and Technology
China
;
_audit_update_record             
;
2022-05-31 deposited with the CCDC.	2022-09-16 downloaded from the CCDC.
;
_audit_creation_date             2022-05-11
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'H10 Na O6, C8 H4 N14 O4, 2(C3 H7 N O)'
_chemical_formula_sum            'C14 H28 N16 Na O12'
_chemical_formula_weight         635.51
_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 0.0181 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'
Na Na 0.1353 0.1239 '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'

_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                   5.0210(3)
_cell_length_b                   26.654(2)
_cell_length_c                   10.3060(7)
_cell_angle_alpha                90
_cell_angle_beta                 98.410(5)
_cell_angle_gamma                90
_cell_volume                     1364.40(16)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2578
_cell_measurement_temperature    193.00
_cell_measurement_theta_max      68.017
_cell_measurement_theta_min      4.644
_shelx_estimated_absorpt_T_max   0.903
_shelx_estimated_absorpt_T_min   0.820
_exptl_absorpt_coefficient_mu    1.295
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.5368
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1645 before and 0.0750 after correction.
The Ratio of minimum to maximum transmission is 0.7128.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.547
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             662
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0718
_diffrn_reflns_av_unetI/netI     0.0668
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            10182
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.321
_diffrn_reflns_theta_min         4.644
_diffrn_ambient_temperature      193.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_source_current           1.1
_diffrn_source_power             0.05500000000000001
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1792
_reflns_number_total             2478
_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 V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_refine_diff_density_max         0.841
_refine_diff_density_min         -0.345
_refine_diff_density_rms         0.114
_refine_ls_extinction_coef       0.0109(19)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     206
_refine_ls_number_reflns         2478
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0846
_refine_ls_R_factor_gt           0.0646
_refine_ls_restrained_S_all      1.019
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1342P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1713
_refine_ls_wR_factor_ref         0.1925
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups, All O(H,H) groups
2. Restrained distances
 Na1-H4A \\sim Na1-H4B
 with sigma of 0.02
 Na1-H6D \\sim Na1-H6E
 with sigma of 0.02
3.a Free rotating group:
 O4(H4A,H4B), O6(H6D,H6E)
3.b Rotating group:
 O5(H5)
3.c Aromatic/amide H refined with riding coordinates:
 C7(H7)
3.d X=CH2 refined with riding coordinates:
 N(HA,HB)
3.e Idealised Me refined as rotating group:
 C5(H5A,H5B,H5C), C6(H6A,H6B,H6C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_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
Na1 Na 0.500000 0.500000 0.500000 0.0263(4) Uani 1 2 d DS . P . .
O4 O 0.7525(4) 0.51366(8) 0.3618(2) 0.0447(6) Uani 1 1 d G . . . .
H4A H 0.905656 0.529455 0.375145 0.067 Uiso 1 1 d DG U . . .
H4B H 0.746285 0.500607 0.283983 0.067 Uiso 1 1 d DG U . . .
O5 O 0.2442(3) 0.56030(8) 0.4220(2) 0.0440(6) Uani 1 1 d . . . . .
H5 H 0.221743 0.581100 0.484986 0.066 Uiso 1 1 d R U . . .
O6 O 0.7060(4) 0.55003(9) 0.6316(2) 0.0473(6) Uani 1 1 d G . . . .
H6D H 0.841442 0.568950 0.619388 0.071 Uiso 1 1 d DG U . . .
H6E H 0.663651 0.559954 0.706369 0.071 Uiso 1 1 d DG U . . .
O1 O 0.8680(5) 0.69194(10) 0.2183(3) 0.0674(8) Uani 1 1 d . . . . .
O2 O 1.0409(5) 0.69338(11) 0.0386(3) 0.0698(8) Uani 1 1 d . . . . .
N1 N 0.8844(5) 0.67594(11) 0.1076(3) 0.0500(7) Uani 1 1 d . . . . .
N2 N 0.7402(4) 0.62133(10) -0.0621(3) 0.0430(6) Uani 1 1 d . . . . .
N3 N 0.5974(4) 0.58494(10) -0.1243(3) 0.0441(6) Uani 1 1 d . . . . .
N4 N 0.2439(4) 0.52604(10) -0.1019(3) 0.0407(6) Uani 1 1 d . . . . .
N5 N 0.1739(4) 0.54816(9) 0.1049(3) 0.0395(6) Uani 1 1 d . . . . .
N6 N 0.3723(4) 0.57696(9) 0.0642(2) 0.0383(6) Uani 1 1 d . . . . .
N N 0.4711(5) 0.62301(11) 0.2538(3) 0.0499(7) Uani 1 1 d . . . . .
HA H 0.346003 0.605734 0.285610 0.060 Uiso 1 1 calc R U . . .
HB H 0.562144 0.646327 0.301807 0.060 Uiso 1 1 calc R U . . .
C1 C 0.7080(5) 0.63553(11) 0.0573(3) 0.0411(7) Uani 1 1 d . . . . .
C2 C 0.5202(5) 0.61426(11) 0.1383(3) 0.0399(7) Uani 1 1 d . . . . .
C3 C 0.1066(5) 0.51885(11) 0.0011(3) 0.0383(7) Uani 1 1 d . . . . .
C4 C 0.4111(5) 0.56330(12) -0.0581(3) 0.0388(7) Uani 1 1 d . . . . .
O3 O 0.0804(5) 0.62138(10) -0.3940(3) 0.0614(7) Uani 1 1 d . . . . .
N8 N 0.3304(5) 0.68831(10) -0.3172(3) 0.0496(7) Uani 1 1 d . . . . .
C5 C 0.4098(7) 0.72346(14) -0.2102(4) 0.0613(10) Uani 1 1 d . . . . .
H5A H 0.603133 0.720109 -0.179603 0.092 Uiso 1 1 calc R U . . .
H5B H 0.309190 0.716130 -0.137802 0.092 Uiso 1 1 calc R U . . .
H5C H 0.370417 0.757794 -0.241287 0.092 Uiso 1 1 calc R U . . .
C6 C 0.4508(8) 0.69364(16) -0.4362(4) 0.0666(11) Uani 1 1 d . . . . .
H6A H 0.538533 0.726478 -0.436552 0.100 Uiso 1 1 calc R U . . .
H6B H 0.310473 0.690951 -0.512714 0.100 Uiso 1 1 calc R U . . .
H6C H 0.584621 0.667107 -0.439773 0.100 Uiso 1 1 calc R U . . .
C7 C 0.1548(6) 0.65200(13) -0.3071(4) 0.0519(8) Uani 1 1 d . . . . .
H7 H 0.081437 0.649441 -0.227452 0.062 Uiso 1 1 calc R U . . .


_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
Na1 O4 2.073(2) 3_666 ?
Na1 O4 2.073(2) . ?
Na1 O5 2.139(2) 3_666 ?
Na1 O5 2.139(2) . ?
Na1 H5 2.5662 . ?
Na1 O6 2.068(2) 3_666 ?
Na1 O6 2.068(2) . ?
O4 H4A 0.8699 . ?
O4 H4B 0.8706 . ?
O5 H5 0.8733 . ?
O6 H6D 0.8703 . ?
O6 H6E 0.8702 . ?
O1 N1 1.232(4) . ?
O2 N1 1.225(4) . ?
N1 C1 1.442(4) . ?
N2 N3 1.316(4) . ?
N2 C1 1.320(4) . ?
N3 C4 1.363(4) . ?
N4 C3 1.361(4) . ?
N4 C4 1.336(4) . ?
N5 N6 1.371(3) . ?
N5 C3 1.328(4) . ?
N6 C2 1.400(4) . ?
N6 C4 1.353(4) . ?
N HA 0.8800 . ?
N HB 0.8800 . ?
N C2 1.271(4) . ?
C1 C2 1.462(4) . ?
C3 C3 1.466(5) 3_565 ?
O3 C7 1.229(4) . ?
N8 C5 1.457(5) . ?
N8 C6 1.452(5) . ?
N8 C7 1.323(4) . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 H7 0.9500 . ?

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
O4 Na1 O4 180.0 3_666 . ?
O4 Na1 O5 90.22(8) 3_666 3_666 ?
O4 Na1 O5 89.78(8) . 3_666 ?
O4 Na1 O5 89.78(8) 3_666 . ?
O4 Na1 O5 90.22(8) . . ?
O4 Na1 H5 101.1 . . ?
O4 Na1 H5 78.9 3_666 . ?
O5 Na1 O5 180.00(8) . 3_666 ?
O5 Na1 H5 161.3 3_666 . ?
O5 Na1 H5 18.7 . . ?
O6 Na1 O4 92.28(8) 3_666 3_666 ?
O6 Na1 O4 92.28(8) . . ?
O6 Na1 O4 87.72(8) . 3_666 ?
O6 Na1 O4 87.72(8) 3_666 . ?
O6 Na1 O5 91.31(9) . 3_666 ?
O6 Na1 O5 88.68(9) 3_666 3_666 ?
O6 Na1 O5 88.69(9) . . ?
O6 Na1 O5 91.31(9) 3_666 . ?
O6 Na1 H5 73.3 . . ?
O6 Na1 H5 106.7 3_666 . ?
O6 Na1 O6 180.0 . 3_666 ?
Na1 O4 H4A 126.3 . . ?
Na1 O4 H4B 128.3 . . ?
H4A O4 H4B 104.5 . . ?
Na1 O5 H5 109.5 . . ?
Na1 O6 H6D 127.3 . . ?
Na1 O6 H6E 127.8 . . ?
H6D O6 H6E 104.4 . . ?
O1 N1 C1 118.1(3) . . ?
O2 N1 O1 122.7(3) . . ?
O2 N1 C1 119.2(3) . . ?
N3 N2 C1 122.2(2) . . ?
N2 N3 C4 115.6(3) . . ?
C4 N4 C3 101.9(2) . . ?
C3 N5 N6 101.1(2) . . ?
N5 N6 C2 125.6(2) . . ?
C4 N6 N5 110.2(2) . . ?
C4 N6 C2 124.2(2) . . ?
HA N HB 120.0 . . ?
C2 N HA 120.0 . . ?
C2 N HB 120.0 . . ?
N1 C1 C2 119.9(3) . . ?
N2 C1 N1 113.4(3) . . ?
N2 C1 C2 126.8(3) . . ?
N6 C2 C1 107.4(3) . . ?
N C2 N6 118.7(3) . . ?
N C2 C1 133.9(3) . . ?
N4 C3 C3 122.5(3) . 3_565 ?
N5 C3 N4 116.6(2) . . ?
N5 C3 C3 121.0(3) . 3_565 ?
N4 C4 N3 126.0(3) . . ?
N4 C4 N6 110.2(2) . . ?
N6 C4 N3 123.7(3) . . ?
C6 N8 C5 118.3(3) . . ?
C7 N8 C5 121.5(3) . . ?
C7 N8 C6 120.2(3) . . ?
N8 C5 H5A 109.5 . . ?
N8 C5 H5B 109.5 . . ?
N8 C5 H5C 109.5 . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
N8 C6 H6A 109.5 . . ?
N8 C6 H6B 109.5 . . ?
N8 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
O3 C7 N8 124.3(3) . . ?
O3 C7 H7 117.9 . . ?
N8 C7 H7 117.9 . . ?

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
O1 N1 C1 N2 179.6(3) . . . . ?
O1 N1 C1 C2 -1.0(4) . . . . ?
O2 N1 C1 N2 0.6(4) . . . . ?
O2 N1 C1 C2 179.9(3) . . . . ?
N1 C1 C2 N6 178.7(2) . . . . ?
N1 C1 C2 N -1.0(5) . . . . ?
N2 N3 C4 N4 179.8(3) . . . . ?
N2 N3 C4 N6 -0.8(4) . . . . ?
N2 C1 C2 N6 -2.1(4) . . . . ?
N2 C1 C2 N 178.2(3) . . . . ?
N3 N2 C1 N1 179.9(2) . . . . ?
N3 N2 C1 C2 0.7(4) . . . . ?
N5 N6 C2 N 0.1(4) . . . . ?
N5 N6 C2 C1 -179.7(2) . . . . ?
N5 N6 C4 N3 -179.4(2) . . . . ?
N5 N6 C4 N4 0.2(3) . . . . ?
N6 N5 C3 N4 0.3(3) . . . . ?
N6 N5 C3 C3 -179.3(3) . . . 3_565 ?
C1 N2 N3 C4 0.9(4) . . . . ?
C2 N6 C4 N3 -1.0(4) . . . . ?
C2 N6 C4 N4 178.6(2) . . . . ?
C3 N4 C4 N3 179.5(3) . . . . ?
C3 N4 C4 N6 0.0(3) . . . . ?
C3 N5 N6 C2 -178.6(2) . . . . ?
C3 N5 N6 C4 -0.3(3) . . . . ?
C4 N4 C3 N5 -0.2(3) . . . . ?
C4 N4 C3 C3 179.4(3) . . . 3_565 ?
C4 N6 C2 N -178.1(3) . . . . ?
C4 N6 C2 C1 2.2(4) . . . . ?
C5 N8 C7 O3 179.9(3) . . . . ?
C6 N8 C7 O3 -0.6(5) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_mo_20220507_wq_nlg_lcc_28_1_0m
_database_code_depnum_ccdc_archive 'CCDC 2176160'
loop_
_audit_author_name
_audit_author_address
a-b
;Nanjing University of Science and Technology
China
;
_audit_update_record             
;
2022-05-31 deposited with the CCDC.	2022-09-16 downloaded from the CCDC.
;
_audit_creation_date             2022-05-13
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '4(C2 H6 O S), C10 H4 N14'
_chemical_formula_sum            'C18 H28 N14 O4 S4'
_chemical_formula_weight         632.78
_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'
S S 0.1246 0.1234 '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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   5.9008(6)
_cell_length_b                   11.3741(9)
_cell_length_c                   11.9467(11)
_cell_angle_alpha                68.425(3)
_cell_angle_beta                 88.011(4)
_cell_angle_gamma                76.253(3)
_cell_volume                     723.05(12)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    1205
_cell_measurement_temperature    193.00
_cell_measurement_theta_max      25.319
_cell_measurement_theta_min      3.164
_shelx_estimated_absorpt_T_max   0.956
_shelx_estimated_absorpt_T_min   0.942
_exptl_absorpt_coefficient_mu    0.381
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6621
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1245 before and 0.0730 after correction.
The Ratio of minimum to maximum transmission is 0.8880.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.453
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             330
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0989
_diffrn_reflns_av_unetI/netI     0.0751
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            15150
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.457
_diffrn_reflns_theta_min         2.147
_diffrn_ambient_temperature      193.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_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_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2085
_reflns_number_total             3306
_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 V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.5 (Bourhis et al., 2015)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_refine_diff_density_max         0.330
_refine_diff_density_min         -0.404
_refine_diff_density_rms         0.076
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     224
_refine_ls_number_reflns         3306
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0995
_refine_ls_R_factor_gt           0.0554
_refine_ls_restrained_S_all      1.037
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0479P)²+0.5222P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1186
_refine_ls_wR_factor_ref         0.1436
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Sof(S2A)=Sof(O2A)=Sof(C8A)=Sof(H8Aa)=Sof(H8Ab)=Sof(H8Ac)=Sof(C9A)=Sof(H9Aa)=
 Sof(H9Ab)=Sof(H9Ac)=1-FVAR(1)
 Sof(S2)=Sof(O2)=Sof(C8)=Sof(H8a)=Sof(H8b)=Sof(H8c)=Sof(C9)=Sof(H9a)=Sof(H9b)=
 Sof(H9c)=FVAR(1)
3.a X=CH2 refined with riding coordinates:
 N7(H7a,H7b)
3.b Idealised Me refined as rotating group:
 C6(H6a,H6b,H6c), C7(H7c,H7d,H7e), C8(H8a,H8b,H8c), C9(H9a,H9b,H9c), C8A(H8Aa,
 H8Ab,H8Ac), C9A(H9Aa,H9Ab,H9Ac)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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
S1 S 0.73326(15) 0.27397(8) -0.14157(7) 0.0321(2) Uani 1 1 d . . . . .
O1 O 0.5235(4) 0.3663(2) -0.2214(2) 0.0411(6) Uani 1 1 d . . . . .
C6 C 0.7432(9) 0.1212(4) -0.1533(4) 0.0630(13) Uani 1 1 d . . . . .
H6A H 0.614443 0.086368 -0.110820 0.095 Uiso 1 1 calc R U . . .
H6B H 0.892457 0.060077 -0.117090 0.095 Uiso 1 1 calc R U . . .
H6C H 0.728206 0.133124 -0.238465 0.095 Uiso 1 1 calc R U . . .
C7 C 0.9782(7) 0.3096(5) -0.2258(4) 0.0553(11) Uani 1 1 d . . . . .
H7C H 0.957984 0.306771 -0.305765 0.083 Uiso 1 1 calc R U . . .
H7D H 1.120283 0.245005 -0.183699 0.083 Uiso 1 1 calc R U . . .
H7E H 0.991716 0.396716 -0.234471 0.083 Uiso 1 1 calc R U . . .
N1 N 0.1365(4) 0.3283(2) 0.0216(2) 0.0289(6) Uani 1 1 d . . . . .
N2 N 0.2701(4) 0.4665(2) 0.0877(2) 0.0244(5) Uani 1 1 d . . . . .
N3 N 0.4240(4) 0.3476(2) 0.1221(2) 0.0233(5) Uani 1 1 d . . . . .
N4 N 0.4598(5) 0.1415(2) 0.1022(2) 0.0333(6) Uani 1 1 d . . . . .
N5 N 0.6586(5) 0.1001(2) 0.1675(2) 0.0336(6) Uani 1 1 d . . . . .
N6 N 1.1283(6) 0.0711(3) 0.3377(3) 0.0540(9) Uani 1 1 d . . . . .
N7 N 0.6946(4) 0.3891(2) 0.2303(2) 0.0284(6) Uani 1 1 d . . . . .
H7A H 0.609191 0.469127 0.212361 0.034 Uiso 1 1 calc R U . . .
H7B H 0.825941 0.362766 0.274828 0.034 Uiso 1 1 calc R U . . .
C1 C 0.1032(5) 0.4475(3) 0.0280(3) 0.0245(6) Uani 1 1 d . . . . .
C2 C 0.3419(5) 0.2655(3) 0.0817(3) 0.0260(6) Uani 1 1 d . . . . .
C3 C 0.7393(5) 0.1782(3) 0.2105(3) 0.0285(7) Uani 1 1 d . . . . .
C4 C 0.6263(5) 0.3094(3) 0.1910(2) 0.0232(6) Uani 1 1 d . . . . .
C5 C 0.9562(6) 0.1191(3) 0.2813(3) 0.0364(8) Uani 1 1 d . . . . .
S2 S 0.2689(3) 0.28121(13) 0.43126(15) 0.0347(5) Uani 0.769(6) 1 d . . P A 1
O2 O 0.0084(6) 0.3379(3) 0.4206(4) 0.0470(11) Uani 0.769(6) 1 d . . P A 1
C8 C 0.3214(15) 0.1355(8) 0.5636(6) 0.0453(17) Uani 0.769(6) 1 d . . P A 1
H8A H 0.489301 0.094702 0.576303 0.068 Uiso 0.769(6) 1 calc R U P A 1
H8B H 0.237694 0.074963 0.553429 0.068 Uiso 0.769(6) 1 calc R U P A 1
H8C H 0.265841 0.157112 0.633604 0.068 Uiso 0.769(6) 1 calc R U P A 1
C9 C 0.3960(14) 0.3768(9) 0.4878(7) 0.0483(18) Uani 0.769(6) 1 d . . P A 1
H9A H 0.312822 0.386772 0.557457 0.073 Uiso 0.769(6) 1 calc R U P A 1
H9B H 0.384507 0.462873 0.424712 0.073 Uiso 0.769(6) 1 calc R U P A 1
H9C H 0.560805 0.333462 0.512474 0.073 Uiso 0.769(6) 1 calc R U P A 1
S2A S 0.1634(12) 0.2935(4) 0.4794(6) 0.0395(18) Uani 0.231(6) 1 d . . P A 2
O2A O 0.136(2) 0.3377(10) 0.3463(9) 0.039(3) Uani 0.231(6) 1 d . . P A 2
C8A C 0.393(6) 0.157(3) 0.521(2) 0.055(8) Uani 0.231(6) 1 d . . P A 2
H8AA H 0.357186 0.092881 0.491342 0.082 Uiso 0.231(6) 1 calc R U P A 2
H8AB H 0.417273 0.118678 0.608619 0.082 Uiso 0.231(6) 1 calc R U P A 2
H8AC H 0.535362 0.181184 0.485099 0.082 Uiso 0.231(6) 1 calc R U P A 2
C9A C 0.311(5) 0.401(3) 0.512(2) 0.047(7) Uani 0.231(6) 1 d . . P A 2
H9AA H 0.444921 0.411592 0.461223 0.071 Uiso 0.231(6) 1 calc R U P A 2
H9AB H 0.365845 0.363786 0.596914 0.071 Uiso 0.231(6) 1 calc R U P A 2
H9AC H 0.202331 0.486403 0.494466 0.071 Uiso 0.231(6) 1 calc R 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
S1 O1 1.507(2) . ?
S1 C6 1.781(4) . ?
S1 C7 1.773(4) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 H7C 0.9800 . ?
C7 H7D 0.9800 . ?
C7 H7E 0.9800 . ?
N1 C1 1.353(4) . ?
N1 C2 1.330(4) . ?
N2 N3 1.363(3) . ?
N2 C1 1.337(4) . ?
N3 C2 1.379(4) . ?
N3 C4 1.360(4) . ?
N4 N5 1.318(4) . ?
N4 C2 1.350(4) . ?
N5 C3 1.354(4) . ?
N6 C5 1.139(4) . ?
N7 H7A 0.8800 . ?
N7 H7B 0.8800 . ?
N7 C4 1.306(4) . ?
C1 C1 1.461(6) 2_565 ?
C3 C4 1.417(4) . ?
C3 C5 1.432(5) . ?
S2 O2 1.509(4) . ?
S2 C8 1.791(7) . ?
S2 C9 1.779(8) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
S2A O2A 1.483(13) . ?
S2A C8A 1.73(3) . ?
S2A C9A 1.81(3) . ?
C8A H8AA 0.9800 . ?
C8A H8AB 0.9800 . ?
C8A H8AC 0.9800 . ?
C9A H9AA 0.9800 . ?
C9A H9AB 0.9800 . ?
C9A H9AC 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
O1 S1 C6 104.65(17) . . ?
O1 S1 C7 105.13(18) . . ?
C7 S1 C6 98.3(2) . . ?
S1 C6 H6A 109.5 . . ?
S1 C6 H6B 109.5 . . ?
S1 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
S1 C7 H7C 109.5 . . ?
S1 C7 H7D 109.5 . . ?
S1 C7 H7E 109.5 . . ?
H7C C7 H7D 109.5 . . ?
H7C C7 H7E 109.5 . . ?
H7D C7 H7E 109.5 . . ?
C2 N1 C1 102.6(2) . . ?
C1 N2 N3 100.7(2) . . ?
N2 N3 C2 110.4(2) . . ?
C4 N3 N2 126.4(2) . . ?
C4 N3 C2 123.1(2) . . ?
N5 N4 C2 116.0(3) . . ?
N4 N5 C3 121.6(3) . . ?
H7A N7 H7B 120.0 . . ?
C4 N7 H7A 120.0 . . ?
C4 N7 H7B 120.0 . . ?
N1 C1 C1 122.4(3) . 2_565 ?
N2 C1 N1 117.0(3) . . ?
N2 C1 C1 120.6(3) . 2_565 ?
N1 C2 N3 109.3(3) . . ?
N1 C2 N4 127.5(3) . . ?
N4 C2 N3 123.2(3) . . ?
N5 C3 C4 125.2(3) . . ?
N5 C3 C5 115.2(3) . . ?
C4 C3 C5 119.6(3) . . ?
N3 C4 C3 110.8(3) . . ?
N7 C4 N3 121.2(3) . . ?
N7 C4 C3 128.0(3) . . ?
N6 C5 C3 179.4(4) . . ?
O2 S2 C8 105.6(4) . . ?
O2 S2 C9 106.2(3) . . ?
C9 S2 C8 98.1(4) . . ?
S2 C8 H8A 109.5 . . ?
S2 C8 H8B 109.5 . . ?
S2 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
S2 C9 H9A 109.5 . . ?
S2 C9 H9B 109.5 . . ?
S2 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
O2A S2A C8A 104.4(11) . . ?
O2A S2A C9A 106.8(10) . . ?
C8A S2A C9A 97.9(14) . . ?
S2A C8A H8AA 109.5 . . ?
S2A C8A H8AB 109.5 . . ?
S2A C8A H8AC 109.5 . . ?
H8AA C8A H8AB 109.5 . . ?
H8AA C8A H8AC 109.5 . . ?
H8AB C8A H8AC 109.5 . . ?
S2A C9A H9AA 109.5 . . ?
S2A C9A H9AB 109.5 . . ?
S2A C9A H9AC 109.5 . . ?
H9AA C9A H9AB 109.5 . . ?
H9AA C9A H9AC 109.5 . . ?
H9AB C9A H9AC 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
N2 N3 C2 N1 -0.1(3) . . . . ?
N2 N3 C2 N4 179.6(3) . . . . ?
N2 N3 C4 N7 -1.1(4) . . . . ?
N2 N3 C4 C3 178.8(3) . . . . ?
N3 N2 C1 N1 0.1(3) . . . . ?
N3 N2 C1 C1 -179.3(3) . . . 2_565 ?
N4 N5 C3 C4 -0.5(5) . . . . ?
N4 N5 C3 C5 179.2(3) . . . . ?
N5 N4 C2 N1 -178.2(3) . . . . ?
N5 N4 C2 N3 2.1(4) . . . . ?
N5 C3 C4 N3 -0.3(4) . . . . ?
N5 C3 C4 N7 179.7(3) . . . . ?
C1 N1 C2 N3 0.2(3) . . . . ?
C1 N1 C2 N4 -179.5(3) . . . . ?
C1 N2 N3 C2 0.0(3) . . . . ?
C1 N2 N3 C4 -177.2(3) . . . . ?
C2 N1 C1 N2 -0.2(3) . . . . ?
C2 N1 C1 C1 179.2(3) . . . 2_565 ?
C2 N3 C4 N7 -178.0(3) . . . . ?
C2 N3 C4 C3 2.0(4) . . . . ?
C2 N4 N5 C3 -0.4(4) . . . . ?
C4 N3 C2 N1 177.2(3) . . . . ?
C4 N3 C2 N4 -3.1(4) . . . . ?
C5 C3 C4 N3 180.0(3) . . . . ?
C5 C3 C4 N7 -0.1(5) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
