# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_6julb_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2210316'
loop_
_audit_author_name
_audit_author_address
'Srinivas D'
;IIT Kanpur
India
;
_audit_update_record             
;
2022-09-29 deposited with the CCDC.	2022-12-23 downloaded from the CCDC.
;
_audit_creation_date             2022-09-26
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C4 H3 N7 O2)'
_chemical_formula_sum            'C8 H6 N14 O4'
_chemical_formula_weight         362.27
_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      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                   8.5317(3)
_cell_length_b                   8.6151(3)
_cell_length_c                   9.1400(3)
_cell_angle_alpha                92.6160(10)
_cell_angle_beta                 93.1460(10)
_cell_angle_gamma                99.8180(10)
_cell_volume                     659.93(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    6759
_cell_measurement_temperature    100
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      3.2
_shelx_estimated_absorpt_T_max   0.956
_shelx_estimated_absorpt_T_min   0.949
_exptl_absorpt_coefficient_mu    0.152
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6130
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'metallic whiteish colourless'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.823
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       irregular
_exptl_crystal_F_000             368
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.3
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0268
_diffrn_reflns_av_unetI/netI     0.0292
_diffrn_reflns_Laue_measured_fraction_full 0.974
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            10100
_diffrn_reflns_point_group_measured_fraction_full 0.974
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.318
_diffrn_reflns_theta_min         2.235
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.974
_diffrn_measured_fraction_theta_max 0.979
_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           1.0
_diffrn_source_power             0.05
_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                2855
_reflns_number_total             3230
_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 (Bruker, 2018)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.3 (Bourhis et al., 2015)'
_refine_diff_density_max         0.431
_refine_diff_density_min         -0.425
_refine_diff_density_rms         0.054
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     243
_refine_ls_number_reflns         3230
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0444
_refine_ls_R_factor_gt           0.0377
_refine_ls_restrained_S_all      1.057
_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)+(0.0326P)²+0.4962P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0869
_refine_ls_wR_factor_ref         0.0913
_refine_special_details          ?
_olex2_refinement_description    
;
1.a Aromatic/amide H refined with riding coordinates:
 N2(H2), N25(H25), N4(H4), N22(H22)
;
_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
O21 O 0.36537(12) 0.83606(11) -0.14600(11) 0.0142(2) Uani 1 1 d . . . . .
O5 O 0.57693(12) 0.61309(12) 0.65812(11) 0.0154(2) Uani 1 1 d . . . . .
O1 O 0.37090(12) 0.92237(12) 0.33336(11) 0.0168(2) Uani 1 1 d . . . . .
O24 O 0.07516(13) 1.05565(12) 0.18478(12) 0.0188(2) Uani 1 1 d . . . . .
N26 N 0.13558(14) 0.66528(13) 0.13763(13) 0.0117(2) Uani 1 1 d . . . . .
N3 N 0.76776(14) 0.87524(14) 0.40762(13) 0.0120(2) Uani 1 1 d . . . . .
N14 N 0.23214(14) 0.39072(13) 0.03427(13) 0.0113(2) Uani 1 1 d . . . . .
N15 N 0.30178(14) 0.28719(14) -0.04537(13) 0.0127(2) Uani 1 1 d . . . . .
N17 N 0.36774(14) 0.51000(13) -0.13332(13) 0.0108(2) Uani 1 1 d . . . . .
N2 N 0.63732(14) 0.92605(14) 0.35415(12) 0.0119(2) Uani 1 1 d . . . . .
H2 H 0.651629 1.001701 0.292195 0.014 Uiso 1 1 calc R U . . .
N25 N 0.08217(14) 0.79345(13) 0.18573(13) 0.0120(2) Uani 1 1 d . . . . .
H25 H 0.015058 0.782561 0.255819 0.014 Uiso 1 1 calc R U . . .
N4 N 0.46828(14) 0.75771(13) 0.49023(13) 0.0121(2) Uani 1 1 d . . . . .
H4 H 0.371434 0.716216 0.512119 0.015 Uiso 1 1 calc R U . . .
N7 N 1.13088(14) 0.66693(14) 0.57107(13) 0.0136(2) Uani 1 1 d . . . . .
N8 N 1.06943(14) 0.62001(14) 0.69231(13) 0.0131(2) Uani 1 1 d . . . . .
N9 N 0.91962(14) 0.64774(13) 0.68439(13) 0.0108(2) Uani 1 1 d . . . . .
N6 N 1.02373(14) 0.72584(14) 0.48454(13) 0.0128(2) Uani 1 1 d . . . . .
N22 N 0.22347(14) 0.94931(13) 0.02000(13) 0.0126(2) Uani 1 1 d . . . . .
H22 H 0.253835 1.042262 -0.015282 0.015 Uiso 1 1 calc R U . . .
N16 N 0.38392(14) 0.35729(13) -0.14660(13) 0.0127(2) Uani 1 1 d . . . . .
C18 C 0.27474(15) 0.52909(15) -0.02337(14) 0.0097(2) Uani 1 1 d . . . . .
C19 C 0.22565(16) 0.67572(15) 0.02720(14) 0.0099(2) Uani 1 1 d . . . . .
C10 C 0.89354(16) 0.71475(15) 0.55846(14) 0.0100(2) Uani 1 1 d . . . . .
C12 C 0.59336(16) 0.70577(15) 0.56051(14) 0.0109(3) Uani 1 1 d . . . . .
C20 C 0.27893(16) 0.82419(15) -0.04291(14) 0.0105(2) Uani 1 1 d . . . . .
C13 C 0.48323(16) 0.87089(16) 0.38715(15) 0.0118(3) Uani 1 1 d . . . . .
C11 C 0.74909(15) 0.77038(15) 0.50568(14) 0.0102(2) Uani 1 1 d . . . . .
C23 C 0.12367(17) 0.94218(16) 0.13443(15) 0.0130(3) Uani 1 1 d . . . . .
H17 H 0.416(2) 0.578(2) -0.193(2) 0.023(5) Uiso 1 1 d . . . . .
H9 H 0.861(3) 0.632(3) 0.761(2) 0.030(5) 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
O21 C20 1.2254(17) . ?
O5 C12 1.2222(17) . ?
O1 C13 1.2124(17) . ?
O24 C23 1.2069(17) . ?
N26 N25 1.3302(16) . ?
N26 C19 1.2990(18) . ?
N3 N2 1.3397(16) . ?
N3 C11 1.2982(17) . ?
N14 N15 1.3592(16) . ?
N14 C18 1.3271(17) . ?
N15 N16 1.2999(17) . ?
N17 N16 1.3468(16) . ?
N17 C18 1.3354(17) . ?
N17 H17 0.89(2) . ?
N2 H2 0.8800 . ?
N2 C13 1.3743(18) . ?
N25 H25 0.8800 . ?
N25 C23 1.3804(18) . ?
N4 H4 0.8800 . ?
N4 C12 1.3659(18) . ?
N4 C13 1.3818(17) . ?
N7 N8 1.3032(17) . ?
N7 N6 1.3544(16) . ?
N8 N9 1.3384(16) . ?
N9 C10 1.3357(17) . ?
N9 H9 0.88(2) . ?
N6 C10 1.3233(17) . ?
N22 H22 0.8800 . ?
N22 C20 1.3651(17) . ?
N22 C23 1.3815(18) . ?
C18 C19 1.4606(18) . ?
C19 C20 1.4703(18) . ?
C10 C11 1.4624(18) . ?
C12 C11 1.4740(18) . ?

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
C19 N26 N25 118.60(11) . . ?
C11 N3 N2 117.51(12) . . ?
C18 N14 N15 105.41(11) . . ?
N16 N15 N14 111.15(11) . . ?
N16 N17 H17 119.6(13) . . ?
C18 N17 N16 108.86(11) . . ?
C18 N17 H17 131.6(13) . . ?
N3 N2 H2 117.0 . . ?
N3 N2 C13 125.99(11) . . ?
C13 N2 H2 117.0 . . ?
N26 N25 H25 117.4 . . ?
N26 N25 C23 125.18(12) . . ?
C23 N25 H25 117.4 . . ?
C12 N4 H4 117.7 . . ?
C12 N4 C13 124.55(12) . . ?
C13 N4 H4 117.7 . . ?
N8 N7 N6 110.82(11) . . ?
N7 N8 N9 106.28(11) . . ?
N8 N9 H9 119.6(14) . . ?
C10 N9 N8 108.70(11) . . ?
C10 N9 H9 131.2(14) . . ?
C10 N6 N7 105.55(11) . . ?
C20 N22 H22 117.3 . . ?
C20 N22 C23 125.45(11) . . ?
C23 N22 H22 117.3 . . ?
N15 N16 N17 106.01(11) . . ?
N14 C18 N17 108.57(11) . . ?
N14 C18 C19 124.61(12) . . ?
N17 C18 C19 126.82(12) . . ?
N26 C19 C18 115.62(12) . . ?
N26 C19 C20 123.36(12) . . ?
C18 C19 C20 121.01(12) . . ?
N9 C10 C11 127.90(12) . . ?
N6 C10 N9 108.63(12) . . ?
N6 C10 C11 123.47(12) . . ?
O5 C12 N4 123.02(12) . . ?
O5 C12 C11 123.47(12) . . ?
N4 C12 C11 113.50(11) . . ?
O21 C20 N22 123.03(12) . . ?
O21 C20 C19 124.04(12) . . ?
N22 C20 C19 112.92(11) . . ?
O1 C13 N2 122.13(13) . . ?
O1 C13 N4 123.22(13) . . ?
N2 C13 N4 114.59(12) . . ?
N3 C11 C10 115.89(12) . . ?
N3 C11 C12 123.53(12) . . ?
C10 C11 C12 120.56(11) . . ?
O24 C23 N25 122.54(13) . . ?
O24 C23 N22 123.13(13) . . ?
N25 C23 N22 114.33(12) . . ?

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
O5 C12 C11 N3 -176.15(13) . . . . ?
O5 C12 C11 C10 5.3(2) . . . . ?
N26 N25 C23 O24 -177.86(13) . . . . ?
N26 N25 C23 N22 2.8(2) . . . . ?
N26 C19 C20 O21 179.12(13) . . . . ?
N26 C19 C20 N22 -0.16(19) . . . . ?
N3 N2 C13 O1 -179.52(13) . . . . ?
N3 N2 C13 N4 2.99(19) . . . . ?
N14 N15 N16 N17 -0.08(15) . . . . ?
N14 C18 C19 N26 0.84(19) . . . . ?
N14 C18 C19 C20 179.83(12) . . . . ?
N15 N14 C18 N17 -0.40(14) . . . . ?
N15 N14 C18 C19 179.41(12) . . . . ?
N17 C18 C19 N26 -179.38(13) . . . . ?
N17 C18 C19 C20 -0.4(2) . . . . ?
N2 N3 C11 C10 178.41(11) . . . . ?
N2 N3 C11 C12 -0.17(19) . . . . ?
N25 N26 C19 C18 -177.69(11) . . . . ?
N25 N26 C19 C20 3.35(19) . . . . ?
N4 C12 C11 N3 4.73(19) . . . . ?
N4 C12 C11 C10 -173.78(11) . . . . ?
N7 N8 N9 C10 -1.28(15) . . . . ?
N7 N6 C10 N9 -1.41(14) . . . . ?
N7 N6 C10 C11 178.03(12) . . . . ?
N8 N7 N6 C10 0.63(15) . . . . ?
N8 N9 C10 N6 1.71(15) . . . . ?
N8 N9 C10 C11 -177.70(12) . . . . ?
N9 C10 C11 N3 158.01(13) . . . . ?
N9 C10 C11 C12 -23.4(2) . . . . ?
N6 N7 N8 N9 0.40(15) . . . . ?
N6 C10 C11 N3 -21.32(19) . . . . ?
N6 C10 C11 C12 157.30(13) . . . . ?
N16 N17 C18 N14 0.37(15) . . . . ?
N16 N17 C18 C19 -179.44(12) . . . . ?
C18 N14 N15 N16 0.30(15) . . . . ?
C18 N17 N16 N15 -0.17(14) . . . . ?
C18 C19 C20 O21 0.2(2) . . . . ?
C18 C19 C20 N22 -179.07(12) . . . . ?
C19 N26 N25 C23 -4.9(2) . . . . ?
C12 N4 C13 O1 -175.04(13) . . . . ?
C12 N4 C13 N2 2.42(19) . . . . ?
C20 N22 C23 O24 -178.54(14) . . . . ?
C20 N22 C23 N25 0.7(2) . . . . ?
C13 N4 C12 O5 175.06(13) . . . . ?
C13 N4 C12 C11 -5.82(18) . . . . ?
C11 N3 N2 C13 -4.0(2) . . . . ?
C23 N22 C20 O21 178.78(13) . . . . ?
C23 N22 C20 C19 -1.93(19) . . . . ?

_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_28julc
_database_code_depnum_ccdc_archive 'CCDC 2210318'
loop_
_audit_author_name
_audit_author_address
'Srinivas D'
;IIT Kanpur
India
;
_audit_update_record             
;
2022-09-29 deposited with the CCDC.	2022-12-23 downloaded from the CCDC.
;
_audit_creation_date             2022-09-26
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C4 H5 N9 O'
_chemical_formula_sum            'C4 H5 N9 O'
_chemical_formula_weight         195.17
_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/n 1'
_space_group_name_Hall           '-P 2yn'
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                   10.633(2)
_cell_length_b                   5.9796(13)
_cell_length_c                   12.194(3)
_cell_angle_alpha                90
_cell_angle_beta                 105.972(6)
_cell_angle_gamma                90
_cell_volume                     745.3(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3953
_cell_measurement_temperature    100
_cell_measurement_theta_max      29.73
_cell_measurement_theta_min      3.48
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.138
_exptl_absorpt_correction_T_max  0.7459
_exptl_absorpt_correction_T_min  0.6840
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   Blessings,1995
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'metallic brownish yellow'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   brownish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.739
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       irregular
_exptl_crystal_F_000             400
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.25
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0574
_diffrn_reflns_av_unetI/netI     0.0361
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            12126
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.780
_diffrn_reflns_theta_min         2.983
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_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           1.0
_diffrn_source_power             0.05
_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                1740
_reflns_number_total             2119
_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 (Bruker, 2018)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.515
_refine_diff_density_min         -0.295
_refine_diff_density_rms         0.064
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     133
_refine_ls_number_reflns         2119
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0564
_refine_ls_R_factor_gt           0.0435
_refine_ls_restrained_S_all      1.058
_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)+(0.0418P)²+0.6186P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1039
_refine_ls_wR_factor_ref         0.1118
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All N(H) groups, All N(H,H) groups
 At 1.5 times of:
  All O(H) groups
2.a Rotating group:
 N12(H12A)
2.b X=CH2 refined with riding coordinates:
 N10(H10A,H10B)
2.c Idealised tetrahedral OH refined as rotating group:
 O14(H14)
;
_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
O14 O 0.90400(12) 0.54836(19) 0.31390(10) 0.0201(3) Uani 1 1 d . . . . .
H14 H 0.933755 0.657075 0.288512 0.030 Uiso 1 1 calc R U . . .
N5 N 0.72727(12) 0.3621(2) 0.60078(10) 0.0117(2) Uani 1 1 d . . . . .
N4 N 0.65205(12) 0.4122(2) 0.66983(10) 0.0110(2) Uani 1 1 d . . . . .
N8 N 0.56096(12) 0.7469(2) 0.57831(10) 0.0119(3) Uani 1 1 d . . . . .
N1 N 0.51487(12) 0.5815(2) 0.74419(11) 0.0133(3) Uani 1 1 d . . . . .
N12 N 0.85953(14) 0.2534(2) 0.45057(12) 0.0173(3) Uani 1 1 d . . . . .
H12A H 0.916997 0.249524 0.412013 0.021 Uiso 1 1 d R U . . .
N10 N 0.63259(13) 0.8627(2) 0.42760(11) 0.0145(3) Uani 1 1 d . . . . .
H10A H 0.580711 0.975500 0.419981 0.017 Uiso 1 1 calc R U . . .
H10B H 0.680959 0.846197 0.382074 0.017 Uiso 1 1 calc R U . . .
N3 N 0.64494(13) 0.2857(2) 0.76102(10) 0.0139(3) Uani 1 1 d . . . . .
N13 N 0.82196(13) 0.6209(2) 0.37885(11) 0.0164(3) Uani 1 1 d . . . . .
N2 N 0.56256(13) 0.3921(2) 0.80392(11) 0.0147(3) Uani 1 1 d . . . . .
C11 C 0.80691(14) 0.4612(2) 0.44587(12) 0.0123(3) Uani 1 1 d . . . . .
C7 C 0.63799(14) 0.7147(2) 0.50929(12) 0.0113(3) Uani 1 1 d . . . . .
C6 C 0.72327(13) 0.5126(2) 0.52175(12) 0.0109(3) Uani 1 1 d . . . . .
C9 C 0.57300(14) 0.5936(2) 0.66064(12) 0.0109(3) Uani 1 1 d . . . . .
H12B H 0.860(2) 0.173(4) 0.5062(19) 0.027(6) 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
O14 H14 0.8200 . ?
O14 N13 1.3988(17) . ?
N5 N4 1.3449(17) . ?
N5 C6 1.3105(18) . ?
N4 N3 1.3640(17) . ?
N4 C9 1.3578(18) . ?
N8 C7 1.3399(19) . ?
N8 C9 1.3395(18) . ?
N1 N2 1.3664(18) . ?
N1 C9 1.3311(19) . ?
N12 H12A 0.8677 . ?
N12 C11 1.3574(19) . ?
N12 H12B 0.83(2) . ?
N10 H10A 0.8600 . ?
N10 H10B 0.8600 . ?
N10 C7 1.3217(18) . ?
N3 N2 1.3030(18) . ?
N13 C11 1.2953(19) . ?
C11 C6 1.481(2) . ?
C7 C6 1.494(2) . ?

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
N13 O14 H14 109.5 . . ?
C6 N5 N4 113.76(12) . . ?
N5 N4 N3 124.25(12) . . ?
N5 N4 C9 125.97(12) . . ?
C9 N4 N3 109.78(12) . . ?
C9 N8 C7 115.06(12) . . ?
C9 N1 N2 105.70(12) . . ?
H12A N12 H12B 125.5 . . ?
C11 N12 H12A 110.2 . . ?
C11 N12 H12B 118.4(15) . . ?
H10A N10 H10B 120.0 . . ?
C7 N10 H10A 120.0 . . ?
C7 N10 H10B 120.0 . . ?
N2 N3 N4 104.52(12) . . ?
C11 N13 O14 109.46(12) . . ?
N3 N2 N1 112.50(12) . . ?
N12 C11 C6 118.35(13) . . ?
N13 C11 N12 125.49(14) . . ?
N13 C11 C6 116.15(13) . . ?
N8 C7 C6 120.75(13) . . ?
N10 C7 N8 118.03(13) . . ?
N10 C7 C6 121.18(13) . . ?
N5 C6 C11 114.42(13) . . ?
N5 C6 C7 121.76(13) . . ?
C11 C6 C7 123.80(12) . . ?
N8 C9 N4 122.55(13) . . ?
N1 C9 N4 107.50(12) . . ?
N1 C9 N8 129.94(13) . . ?

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
O14 N13 C11 N12 -1.6(2) . . . . ?
O14 N13 C11 C6 179.34(12) . . . . ?
N5 N4 N3 N2 179.88(13) . . . . ?
N5 N4 C9 N8 0.3(2) . . . . ?
N5 N4 C9 N1 179.54(13) . . . . ?
N4 N5 C6 C11 179.28(12) . . . . ?
N4 N5 C6 C7 -2.18(19) . . . . ?
N4 N3 N2 N1 0.47(16) . . . . ?
N8 C7 C6 N5 -0.9(2) . . . . ?
N8 C7 C6 C11 177.48(13) . . . . ?
N12 C11 C6 N5 11.48(19) . . . . ?
N12 C11 C6 C7 -167.03(13) . . . . ?
N10 C7 C6 N5 -178.45(13) . . . . ?
N10 C7 C6 C11 0.0(2) . . . . ?
N3 N4 C9 N8 179.99(13) . . . . ?
N3 N4 C9 N1 -0.75(16) . . . . ?
N13 C11 C6 N5 -169.39(13) . . . . ?
N13 C11 C6 C7 12.1(2) . . . . ?
N2 N1 C9 N4 0.99(15) . . . . ?
N2 N1 C9 N8 -179.82(14) . . . . ?
C7 N8 C9 N4 -3.4(2) . . . . ?
C7 N8 C9 N1 177.47(14) . . . . ?
C6 N5 N4 N3 -177.07(13) . . . . ?
C6 N5 N4 C9 2.6(2) . . . . ?
C9 N4 N3 N2 0.17(15) . . . . ?
C9 N8 C7 N10 -178.72(13) . . . . ?
C9 N8 C7 C6 3.67(19) . . . . ?
C9 N1 N2 N3 -0.94(16) . . . . ?

_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_6sepb_o_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2210317'
loop_
_audit_author_name
_audit_author_address
'Srinivas D'
;IIT Kanpur
India
;
_audit_update_record             
;
2022-09-29 deposited with the CCDC.	2022-12-23 downloaded from the CCDC.
;
_audit_creation_date             2022-09-26
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C4 H2 N7 O2, H2 O, C3 H7 N8'
_chemical_formula_sum            'C7 H11 N15 O3'
_chemical_formula_weight         353.31
_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      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                   6.6541(13)
_cell_length_b                   9.5463(18)
_cell_length_c                   10.9893(19)
_cell_angle_alpha                105.143(6)
_cell_angle_beta                 92.926(7)
_cell_angle_gamma                96.537(7)
_cell_volume                     667.1(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4736
_cell_measurement_temperature    100
_cell_measurement_theta_max      28.28
_cell_measurement_theta_min      2.23
_shelx_estimated_absorpt_T_max   0.972
_shelx_estimated_absorpt_T_min   0.958
_exptl_absorpt_coefficient_mu    0.144
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6739
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1088 before and 0.0542 after correction.
The Ratio of minimum to maximum transmission is 0.9037.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.759
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       irregular
_exptl_crystal_F_000             364
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0411
_diffrn_reflns_av_unetI/netI     0.0399
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            11300
_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         28.354
_diffrn_reflns_theta_min         1.927
_diffrn_ambient_temperature      100
_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           1.0
_diffrn_source_power             0.05
_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                2760
_reflns_number_total             3323
_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 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.3 (Bourhis et al., 2015)'
_refine_diff_density_max         0.340
_refine_diff_density_min         -0.297
_refine_diff_density_rms         0.057
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     230
_refine_ls_number_reflns         3323
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0496
_refine_ls_R_factor_gt           0.0386
_refine_ls_restrained_S_all      1.038
_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)+(0.0466P)²+0.2946P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0964
_refine_ls_wR_factor_ref         0.1034
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All N(H) groups, All N(H,H) groups
 At 1.5 times of:
  All O(H,H) groups
2.a Free rotating group:
 O002(H00A,H00B)
2.b Rotating group:
 N22(H22A,H22B)
2.c Aromatic/amide H refined with riding coordinates:
 N8(H8), N11(H11), N18(H18)
2.d X=CH2 refined with riding coordinates:
 N24(H24A,H24B), N17(H17A,H17B)
;
_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
O13 O 0.34495(16) 0.92780(11) 0.70701(9) 0.0178(2) Uani 1 1 d . . . . .
O002 O 0.58482(18) 1.20563(12) 0.54954(10) 0.0207(2) Uani 1 1 d G . . . .
H00A H 0.604939 1.142727 0.482270 0.031 Uiso 1 1 d G U . . .
H00B H 0.631006 1.287487 0.537971 0.031 Uiso 1 1 d G U . . .
O10 O 0.52397(17) 1.42241(11) 0.83682(10) 0.0191(2) Uani 1 1 d . . . . .
N21 N 0.22418(18) 0.28748(13) 0.39723(11) 0.0134(2) Uani 1 1 d . . . . .
N15 N 0.12996(18) 0.33873(13) 0.58678(11) 0.0131(2) Uani 1 1 d . . . . .
N8 N 0.40792(18) 1.30118(13) 0.97770(11) 0.0147(3) Uani 1 1 d . . . . .
H8 H 0.428283 1.383342 1.038662 0.018 Uiso 1 1 calc R U . . .
N11 N 0.42439(19) 1.17562(13) 0.76837(11) 0.0147(2) Uani 1 1 d . . . . .
H11 H 0.449206 1.175825 0.690519 0.018 Uiso 1 1 calc R U . . .
N2 N 0.20573(18) 0.93135(13) 1.08306(11) 0.0139(2) Uani 1 1 d . . . . .
N7 N 0.33108(18) 1.17930(13) 1.00815(11) 0.0138(2) Uani 1 1 d . . . . .
N14 N 0.08506(18) 0.18689(12) 0.54490(11) 0.0140(2) Uani 1 1 d . . . . .
N3 N 0.12314(18) 0.79571(13) 1.08163(11) 0.0149(3) Uani 1 1 d . . . . .
N19 N 0.24979(18) 0.54449(13) 0.53946(11) 0.0143(2) Uani 1 1 d . . . . .
N4 N 0.08907(19) 0.71471(13) 0.96393(11) 0.0163(3) Uani 1 1 d . . . . .
N18 N 0.17929(18) 0.56976(13) 0.66147(11) 0.0139(2) Uani 1 1 d . . . . .
H18 H 0.182773 0.657655 0.713412 0.017 Uiso 1 1 calc R U . . .
N5 N 0.14906(19) 0.79507(13) 0.88437(11) 0.0155(3) Uani 1 1 d . . . . .
N24 N 0.14793(19) 0.03008(13) 0.34998(11) 0.0172(3) Uani 1 1 d . . . . .
H24A H 0.102095 -0.049018 0.372209 0.021 Uiso 1 1 calc R U . . .
H24B H 0.193066 0.022130 0.274901 0.021 Uiso 1 1 calc R U . . .
N17 N 0.0291(2) 0.43043(13) 0.79493(11) 0.0177(3) Uani 1 1 d . . . . .
H17A H 0.020312 0.507859 0.857802 0.021 Uiso 1 1 calc R U . . .
H17B H -0.013648 0.342338 0.801758 0.021 Uiso 1 1 calc R U . . .
N22 N 0.3098(2) 0.29817(14) 0.28591(11) 0.0176(3) Uani 1 1 d . . . . .
H22A H 0.414633 0.251216 0.275804 0.021 Uiso 1 1 d R U . . .
H22B H 0.222174 0.260289 0.220985 0.021 Uiso 1 1 d R U . . .
C20 C 0.2138(2) 0.40184(15) 0.50060(13) 0.0131(3) Uani 1 1 d . . . . .
C6 C 0.3020(2) 1.05599(15) 0.92080(12) 0.0120(3) Uani 1 1 d . . . . .
C23 C 0.1490(2) 0.16095(15) 0.42943(13) 0.0130(3) Uani 1 1 d . . . . .
C16 C 0.1065(2) 0.44642(15) 0.69029(13) 0.0134(3) Uani 1 1 d . . . . .
C9 C 0.4570(2) 1.30776(15) 0.85956(13) 0.0147(3) Uani 1 1 d . . . . .
C1 C 0.2197(2) 0.92729(15) 0.96062(12) 0.0123(3) Uani 1 1 d . . . . .
C12 C 0.3561(2) 1.04370(15) 0.78975(13) 0.0135(3) Uani 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
O13 C12 1.2269(17) . ?
O002 H00A 0.8494 . ?
O002 H00B 0.8500 . ?
O10 C9 1.2255(18) . ?
N21 N22 1.3980(16) . ?
N21 C20 1.3654(18) . ?
N21 C23 1.3922(18) . ?
N15 N14 1.3932(16) . ?
N15 C20 1.3589(18) . ?
N15 C16 1.3486(17) . ?
N8 H8 0.8800 . ?
N8 N7 1.3463(16) . ?
N8 C9 1.3703(18) . ?
N11 H11 0.8800 . ?
N11 C9 1.3775(18) . ?
N11 C12 1.3722(19) . ?
N2 N3 1.3437(17) . ?
N2 C1 1.3442(17) . ?
N7 C6 1.2975(18) . ?
N14 C23 1.3295(18) . ?
N3 N4 1.3152(17) . ?
N19 N18 1.4131(16) . ?
N19 C20 1.3060(19) . ?
N4 N5 1.3523(17) . ?
N18 H18 0.8800 . ?
N18 C16 1.3424(18) . ?
N5 C1 1.3372(18) . ?
N24 H24A 0.8800 . ?
N24 H24B 0.8800 . ?
N24 C23 1.3231(18) . ?
N17 H17A 0.8800 . ?
N17 H17B 0.8800 . ?
N17 C16 1.3209(18) . ?
N22 H22A 0.8677 . ?
N22 H22B 0.8686 . ?
C6 C1 1.4675(19) . ?
C6 C12 1.4803(19) . ?

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
H00A O002 H00B 104.6 . . ?
C20 N21 N22 125.42(12) . . ?
C20 N21 C23 106.56(11) . . ?
C23 N21 N22 127.83(11) . . ?
C20 N15 N14 114.30(11) . . ?
C16 N15 N14 137.70(12) . . ?
C16 N15 C20 107.94(12) . . ?
N7 N8 H8 117.3 . . ?
N7 N8 C9 125.35(12) . . ?
C9 N8 H8 117.3 . . ?
C9 N11 H11 117.5 . . ?
C12 N11 H11 117.5 . . ?
C12 N11 C9 124.94(12) . . ?
N3 N2 C1 104.79(11) . . ?
C6 N7 N8 118.84(12) . . ?
C23 N14 N15 101.15(11) . . ?
N4 N3 N2 109.41(11) . . ?
C20 N19 N18 100.77(11) . . ?
N3 N4 N5 109.75(11) . . ?
N19 N18 H18 123.3 . . ?
C16 N18 N19 113.34(11) . . ?
C16 N18 H18 123.3 . . ?
C1 N5 N4 104.38(11) . . ?
H24A N24 H24B 120.0 . . ?
C23 N24 H24A 120.0 . . ?
C23 N24 H24B 120.0 . . ?
H17A N17 H17B 120.0 . . ?
C16 N17 H17A 120.0 . . ?
C16 N17 H17B 120.0 . . ?
N21 N22 H22A 110.0 . . ?
N21 N22 H22B 110.3 . . ?
H22A N22 H22B 108.4 . . ?
N15 C20 N21 104.54(12) . . ?
N19 C20 N21 141.62(13) . . ?
N19 C20 N15 113.78(12) . . ?
N7 C6 C1 116.03(12) . . ?
N7 C6 C12 122.35(13) . . ?
C1 C6 C12 121.57(12) . . ?
N14 C23 N21 113.43(12) . . ?
N24 C23 N21 121.02(12) . . ?
N24 C23 N14 125.54(13) . . ?
N18 C16 N15 104.17(12) . . ?
N17 C16 N15 126.70(13) . . ?
N17 C16 N18 129.13(13) . . ?
O10 C9 N8 122.56(13) . . ?
O10 C9 N11 122.69(13) . . ?
N8 C9 N11 114.75(12) . . ?
N2 C1 C6 122.11(12) . . ?
N5 C1 N2 111.67(12) . . ?
N5 C1 C6 126.21(12) . . ?
O13 C12 N11 122.08(13) . . ?
O13 C12 C6 124.32(13) . . ?
N11 C12 C6 113.59(12) . . ?

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
N15 N14 C23 N21 -1.79(15) . . . . ?
N15 N14 C23 N24 177.12(14) . . . . ?
N8 N7 C6 C1 179.47(11) . . . . ?
N8 N7 C6 C12 1.9(2) . . . . ?
N2 N3 N4 N5 0.16(15) . . . . ?
N7 N8 C9 O10 178.93(13) . . . . ?
N7 N8 C9 N11 -0.8(2) . . . . ?
N7 C6 C1 N2 -10.4(2) . . . . ?
N7 C6 C1 N5 169.05(13) . . . . ?
N7 C6 C12 O13 174.42(14) . . . . ?
N7 C6 C12 N11 -4.60(19) . . . . ?
N14 N15 C20 N21 0.26(16) . . . . ?
N14 N15 C20 N19 178.11(12) . . . . ?
N14 N15 C16 N18 -177.20(15) . . . . ?
N14 N15 C16 N17 2.9(3) . . . . ?
N3 N2 C1 N5 0.03(15) . . . . ?
N3 N2 C1 C6 179.56(12) . . . . ?
N3 N4 N5 C1 -0.13(15) . . . . ?
N19 N18 C16 N15 0.30(16) . . . . ?
N19 N18 C16 N17 -179.82(14) . . . . ?
N4 N5 C1 N2 0.06(15) . . . . ?
N4 N5 C1 C6 -179.44(13) . . . . ?
N18 N19 C20 N21 176.33(19) . . . . ?
N18 N19 C20 N15 -0.31(15) . . . . ?
N22 N21 C20 N15 -176.65(12) . . . . ?
N22 N21 C20 N19 6.5(3) . . . . ?
N22 N21 C23 N14 177.27(13) . . . . ?
N22 N21 C23 N24 -1.7(2) . . . . ?
C20 N21 C23 N14 2.07(16) . . . . ?
C20 N21 C23 N24 -176.89(13) . . . . ?
C20 N15 N14 C23 0.93(15) . . . . ?
C20 N15 C16 N18 -0.47(15) . . . . ?
C20 N15 C16 N17 179.64(14) . . . . ?
C20 N19 N18 C16 0.00(15) . . . . ?
C23 N21 C20 N15 -1.30(15) . . . . ?
C23 N21 C20 N19 -178.13(19) . . . . ?
C16 N15 N14 C23 177.51(16) . . . . ?
C16 N15 C20 N21 -177.32(11) . . . . ?
C16 N15 C20 N19 0.53(17) . . . . ?
C9 N8 N7 C6 1.0(2) . . . . ?
C9 N11 C12 O13 -174.13(14) . . . . ?
C9 N11 C12 C6 4.9(2) . . . . ?
C1 N2 N3 N4 -0.12(14) . . . . ?
C1 C6 C12 O13 -3.0(2) . . . . ?
C1 C6 C12 N11 177.95(12) . . . . ?
C12 N11 C9 O10 177.77(13) . . . . ?
C12 N11 C9 N8 -2.5(2) . . . . ?
C12 C6 C1 N2 167.21(12) . . . . ?
C12 C6 C1 N5 -13.3(2) . . . . ?

_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_7decc_o_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2225571'
loop_
_audit_author_name
_audit_author_address
'Srinivas Dharavath'
;IIT Kanpur
India
;
_audit_update_record             
;
2022-12-10 deposited with the CCDC.	2022-12-23 downloaded from the CCDC.
;
_audit_creation_date             2022-12-08
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C2 H6 O S, C5 H4 N10 O'
_chemical_formula_sum            'C7 H10 N10 O2 S'
_chemical_formula_weight         298.31
_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                   5.4454(3)
_cell_length_b                   13.7553(7)
_cell_length_c                   16.7080(9)
_cell_angle_alpha                100.096(2)
_cell_angle_beta                 98.259(2)
_cell_angle_gamma                94.944(2)
_cell_volume                     1211.33(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9972
_cell_measurement_temperature    100
_cell_measurement_theta_max      28.35
_cell_measurement_theta_min      2.51
_shelx_estimated_absorpt_T_max   0.972
_shelx_estimated_absorpt_T_min   0.963
_exptl_absorpt_coefficient_mu    0.291
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6627
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1170 before and 0.0527 after correction.
The Ratio of minimum to maximum transmission is 0.8887.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear orangish orange'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   orangish
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.636
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       irregular
_exptl_crystal_F_000             616
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0404
_diffrn_reflns_av_unetI/netI     0.0314
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            30811
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.351
_diffrn_reflns_theta_min         2.142
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.993
_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           0.0
_diffrn_source_power             0.0
_diffrn_source_voltage           0.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5112
_reflns_number_total             6024
_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 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.3 (Bourhis et al., 2015)'
_refine_diff_density_max         0.377
_refine_diff_density_min         -0.460
_refine_diff_density_rms         0.059
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.099
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     365
_refine_ls_number_reflns         6024
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0530
_refine_ls_R_factor_gt           0.0418
_refine_ls_restrained_S_all      1.099
_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)+(0.0271P)²+1.0961P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0880
_refine_ls_wR_factor_ref         0.0921
_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.a X=CH2 refined with riding coordinates:
 N10(H10A,H10B), N20(H20A,H20B), N17(H17A,H17B), N7(H7A,H7B)
2.b Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C12(H12A,H12B,H12C), C14(H14A,H14B,H14C), C11(H11A,H11B,
 H11C)
;
_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
S2 S -0.26901(8) 0.08722(3) 0.41015(3) 0.01774(10) Uani 1 1 d . . . . .
S1 S 1.15854(9) 0.89675(3) 1.14760(3) 0.01874(10) Uani 1 1 d . . . . .
O2 O 1.0377(2) 0.64374(9) 0.96233(8) 0.0161(3) Uani 1 1 d . . . . .
O1 O -0.1769(2) 0.40594(9) 0.52450(8) 0.0166(3) Uani 1 1 d . . . . .
O3 O 1.2939(3) 0.80589(10) 1.15254(8) 0.0219(3) Uani 1 1 d . . . . .
O4 O -0.1826(2) 0.19565(9) 0.40975(8) 0.0191(3) Uani 1 1 d . . . . .
N12 N 0.9913(3) 0.27852(10) 0.73647(9) 0.0141(3) Uani 1 1 d . . . . .
N11 N 1.0778(3) 0.35326(10) 0.80033(9) 0.0136(3) Uani 1 1 d . . . . .
N18 N 1.2304(3) 0.50790(11) 0.93297(9) 0.0136(3) Uani 1 1 d . . . . .
N9 N 0.1163(3) 0.46623(10) 0.63369(9) 0.0136(3) Uani 1 1 d . . . . .
N2 N 0.1622(3) 0.72423(11) 0.79261(9) 0.0159(3) Uani 1 1 d . . . . .
N10 N 0.1438(3) 0.31133(11) 0.54908(9) 0.0171(3) Uani 1 1 d . . . . .
H10A H 0.283859 0.300921 0.578126 0.020 Uiso 1 1 calc R U . . .
H10B H 0.073057 0.267309 0.505263 0.020 Uiso 1 1 calc R U . . .
N16 N 0.6125(3) 0.33983(11) 0.69146(9) 0.0146(3) Uani 1 1 d . . . . .
N1 N 0.1490(3) 0.63884(11) 0.73912(9) 0.0147(3) Uani 1 1 d . . . . .
N20 N 1.3981(3) 0.63524(11) 1.04911(9) 0.0176(3) Uani 1 1 d . . . . .
H20A H 1.526393 0.604388 1.064777 0.021 Uiso 1 1 calc R U . . .
H20B H 1.378879 0.693591 1.077419 0.021 Uiso 1 1 calc R U . . .
N15 N 0.7447(3) 0.18300(11) 0.63326(9) 0.0181(3) Uani 1 1 d . . . . .
N13 N 1.1106(3) 0.19706(11) 0.71638(10) 0.0186(3) Uani 1 1 d . . . . .
N17 N 0.5522(3) 0.49260(11) 0.76054(9) 0.0159(3) Uani 1 1 d . . . . .
H17A H 0.412968 0.490553 0.725931 0.019 Uiso 1 1 calc R U . . .
H17B H 0.600234 0.544494 0.800502 0.019 Uiso 1 1 calc R U . . .
N7 N -0.4347(3) 0.67349(11) 0.61912(9) 0.0176(3) Uani 1 1 d . . . . .
H7A H -0.548422 0.715055 0.616596 0.021 Uiso 1 1 calc R U . . .
H7B H -0.451495 0.618215 0.582199 0.021 Uiso 1 1 calc R U . . .
N8 N -0.2432(3) 0.49923(11) 0.56192(9) 0.0159(3) Uani 1 1 d . . . . .
N14 N 0.9599(3) 0.14196(11) 0.65465(10) 0.0202(3) Uani 1 1 d . . . . .
N6 N -0.2128(3) 0.77763(11) 0.73422(10) 0.0186(3) Uani 1 1 d . . . . .
N19 N 0.8926(3) 0.58301(11) 0.89107(9) 0.0167(3) Uani 1 1 d . . . . .
N3 N 0.3490(3) 0.75406(12) 0.85797(10) 0.0213(3) Uani 1 1 d . . . . .
N4 N 0.2893(3) 0.83737(12) 0.89484(10) 0.0242(4) Uani 1 1 d . . . . .
N5 N 0.0712(3) 0.86404(12) 0.85660(10) 0.0243(4) Uani 1 1 d . . . . .
C9 C 1.0163(3) 0.50602(12) 0.87838(10) 0.0127(3) Uani 1 1 d . . . . .
C4 C -0.0626(3) 0.52868(12) 0.62422(10) 0.0131(3) Uani 1 1 d . . . . .
C5 C 0.0405(3) 0.39255(13) 0.57110(10) 0.0141(3) Uani 1 1 d . . . . .
C3 C -0.0489(3) 0.62360(12) 0.68217(10) 0.0132(3) Uani 1 1 d . . . . .
C6 C 0.7676(3) 0.26905(13) 0.68582(10) 0.0146(3) Uani 1 1 d . . . . .
C10 C 1.2346(3) 0.59404(12) 0.98321(10) 0.0134(3) Uani 1 1 d . . . . .
C7 C 0.6892(3) 0.41763(12) 0.75249(10) 0.0131(3) Uani 1 1 d . . . . .
C8 C 0.9281(3) 0.42198(12) 0.80894(10) 0.0124(3) Uani 1 1 d . . . . .
C1 C -0.0083(4) 0.79093(13) 0.79214(11) 0.0183(4) Uani 1 1 d . . . . .
C2 C -0.2378(3) 0.69417(13) 0.67857(11) 0.0150(3) Uani 1 1 d . . . . .
C13 C -0.5826(4) 0.08498(14) 0.43090(12) 0.0227(4) Uani 1 1 d . . . . .
H13A H -0.581685 0.118786 0.487696 0.034 Uiso 1 1 calc R U . . .
H13B H -0.656915 0.015902 0.423564 0.034 Uiso 1 1 calc R U . . .
H13C H -0.680799 0.119021 0.392807 0.034 Uiso 1 1 calc R U . . .
C12 C 1.3222(4) 0.96915(14) 1.08999(13) 0.0240(4) Uani 1 1 d . . . . .
H12A H 1.490618 0.992789 1.120276 0.036 Uiso 1 1 calc R U . . .
H12B H 1.232785 1.026229 1.081269 0.036 Uiso 1 1 calc R U . . .
H12C H 1.333683 0.928459 1.036586 0.036 Uiso 1 1 calc R U . . .
C14 C -0.3384(4) 0.02838(14) 0.30429(12) 0.0245(4) Uani 1 1 d . . . . .
H14A H -0.456348 0.064765 0.274555 0.037 Uiso 1 1 calc R U . . .
H14B H -0.412894 -0.040214 0.299716 0.037 Uiso 1 1 calc R U . . .
H14C H -0.184243 0.028258 0.280415 0.037 Uiso 1 1 calc R U . . .
C11 C 0.8830(4) 0.85788(16) 1.07302(15) 0.0306(5) Uani 1 1 d . . . . .
H11A H 0.925656 0.818003 1.023392 0.046 Uiso 1 1 calc R U . . .
H11B H 0.809235 0.916426 1.058895 0.046 Uiso 1 1 calc R U . . .
H11C H 0.762561 0.817869 1.095789 0.046 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
S2 O4 1.5263(13) . ?
S2 C13 1.789(2) . ?
S2 C14 1.7831(19) . ?
S1 O3 1.5132(13) . ?
S1 C12 1.773(2) . ?
S1 C11 1.784(2) . ?
O2 N19 1.4166(18) . ?
O2 C10 1.357(2) . ?
O1 N8 1.4253(19) . ?
O1 C5 1.366(2) . ?
N12 N11 1.343(2) . ?
N12 N13 1.359(2) . ?
N12 C6 1.362(2) . ?
N11 C8 1.303(2) . ?
N18 C9 1.368(2) . ?
N18 C10 1.323(2) . ?
N9 C4 1.364(2) . ?
N9 C5 1.313(2) . ?
N2 N1 1.335(2) . ?
N2 N3 1.359(2) . ?
N2 C1 1.361(2) . ?
N10 H10A 0.8800 . ?
N10 H10B 0.8800 . ?
N10 C5 1.313(2) . ?
N16 C6 1.343(2) . ?
N16 C7 1.333(2) . ?
N1 C3 1.307(2) . ?
N20 H20A 0.8800 . ?
N20 H20B 0.8800 . ?
N20 C10 1.319(2) . ?
N15 N14 1.373(2) . ?
N15 C6 1.329(2) . ?
N13 N14 1.299(2) . ?
N17 H17A 0.8800 . ?
N17 H17B 0.8800 . ?
N17 C7 1.323(2) . ?
N7 H7A 0.8800 . ?
N7 H7B 0.8800 . ?
N7 C2 1.326(2) . ?
N8 C4 1.305(2) . ?
N6 C1 1.343(2) . ?
N6 C2 1.328(2) . ?
N19 C9 1.306(2) . ?
N3 N4 1.293(2) . ?
N4 N5 1.376(2) . ?
N5 C1 1.331(2) . ?
C9 C8 1.479(2) . ?
C4 C3 1.472(2) . ?
C3 C2 1.476(2) . ?
C7 C8 1.483(2) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 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
O4 S2 C13 105.86(8) . . ?
O4 S2 C14 105.15(9) . . ?
C14 S2 C13 97.90(10) . . ?
O3 S1 C12 106.64(9) . . ?
O3 S1 C11 106.89(9) . . ?
C12 S1 C11 97.65(11) . . ?
C10 O2 N19 105.99(12) . . ?
C5 O1 N8 105.94(12) . . ?
N11 N12 N13 124.09(14) . . ?
N11 N12 C6 126.03(15) . . ?
N13 N12 C6 109.75(14) . . ?
C8 N11 N12 113.14(14) . . ?
C10 N18 C9 101.69(14) . . ?
C5 N9 C4 102.39(14) . . ?
N1 N2 N3 123.23(15) . . ?
N1 N2 C1 126.07(15) . . ?
N3 N2 C1 110.66(15) . . ?
H10A N10 H10B 120.0 . . ?
C5 N10 H10A 120.0 . . ?
C5 N10 H10B 120.0 . . ?
C7 N16 C6 114.93(15) . . ?
C3 N1 N2 113.18(15) . . ?
H20A N20 H20B 120.0 . . ?
C10 N20 H20A 120.0 . . ?
C10 N20 H20B 120.0 . . ?
C6 N15 N14 104.70(14) . . ?
N14 N13 N12 104.27(14) . . ?
H17A N17 H17B 120.0 . . ?
C7 N17 H17A 120.0 . . ?
C7 N17 H17B 120.0 . . ?
H7A N7 H7B 120.0 . . ?
C2 N7 H7A 120.0 . . ?
C2 N7 H7B 120.0 . . ?
C4 N8 O1 102.62(13) . . ?
N13 N14 N15 113.29(14) . . ?
C2 N6 C1 115.12(15) . . ?
C9 N19 O2 103.12(13) . . ?
N4 N3 N2 103.84(15) . . ?
N3 N4 N5 113.33(15) . . ?
C1 N5 N4 105.12(16) . . ?
N18 C9 C8 122.37(15) . . ?
N19 C9 N18 116.14(15) . . ?
N19 C9 C8 121.49(15) . . ?
N9 C4 C3 120.77(15) . . ?
N8 C4 N9 116.39(15) . . ?
N8 C4 C3 122.84(15) . . ?
N9 C5 O1 112.65(15) . . ?
N10 C5 O1 118.25(15) . . ?
N10 C5 N9 129.10(16) . . ?
N1 C3 C4 112.62(15) . . ?
N1 C3 C2 122.76(16) . . ?
C4 C3 C2 124.62(15) . . ?
N16 C6 N12 122.24(15) . . ?
N15 C6 N12 108.00(15) . . ?
N15 C6 N16 129.74(16) . . ?
N18 C10 O2 113.06(14) . . ?
N20 C10 O2 117.80(15) . . ?
N20 C10 N18 129.13(16) . . ?
N16 C7 C8 120.79(15) . . ?
N17 C7 N16 118.89(15) . . ?
N17 C7 C8 120.29(15) . . ?
N11 C8 C9 115.01(14) . . ?
N11 C8 C7 122.71(15) . . ?
C9 C8 C7 122.27(15) . . ?
N6 C1 N2 122.14(16) . . ?
N5 C1 N2 107.04(17) . . ?
N5 C1 N6 130.81(18) . . ?
N7 C2 N6 119.90(16) . . ?
N7 C2 C3 119.39(16) . . ?
N6 C2 C3 120.71(16) . . ?
S2 C13 H13A 109.5 . . ?
S2 C13 H13B 109.5 . . ?
S2 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
S1 C12 H12A 109.5 . . ?
S1 C12 H12B 109.5 . . ?
S1 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
S2 C14 H14A 109.5 . . ?
S2 C14 H14B 109.5 . . ?
S2 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
S1 C11 H11A 109.5 . . ?
S1 C11 H11B 109.5 . . ?
S1 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 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
O2 N19 C9 N18 -0.3(2) . . . . ?
O2 N19 C9 C8 179.56(14) . . . . ?
O1 N8 C4 N9 -0.48(19) . . . . ?
O1 N8 C4 C3 179.73(15) . . . . ?
N12 N11 C8 C9 -179.78(14) . . . . ?
N12 N11 C8 C7 -1.0(2) . . . . ?
N12 N13 N14 N15 -0.5(2) . . . . ?
N11 N12 N13 N14 176.79(15) . . . . ?
N11 N12 C6 N16 4.9(3) . . . . ?
N11 N12 C6 N15 -176.67(15) . . . . ?
N18 C9 C8 N11 -4.5(2) . . . . ?
N18 C9 C8 C7 176.68(15) . . . . ?
N9 C4 C3 N1 1.1(2) . . . . ?
N9 C4 C3 C2 -177.78(16) . . . . ?
N2 N1 C3 C4 -179.32(14) . . . . ?
N2 N1 C3 C2 -0.4(2) . . . . ?
N2 N3 N4 N5 -0.1(2) . . . . ?
N16 C7 C8 N11 2.6(3) . . . . ?
N16 C7 C8 C9 -178.63(15) . . . . ?
N1 N2 N3 N4 -178.15(16) . . . . ?
N1 N2 C1 N6 -1.5(3) . . . . ?
N1 N2 C1 N5 178.44(16) . . . . ?
N1 C3 C2 N7 -179.69(16) . . . . ?
N1 C3 C2 N6 0.1(3) . . . . ?
N13 N12 N11 C8 -178.14(15) . . . . ?
N13 N12 C6 N16 -179.08(16) . . . . ?
N13 N12 C6 N15 -0.6(2) . . . . ?
N17 C7 C8 N11 -175.37(16) . . . . ?
N17 C7 C8 C9 3.4(2) . . . . ?
N8 O1 C5 N9 0.61(19) . . . . ?
N8 O1 C5 N10 -179.47(15) . . . . ?
N8 C4 C3 N1 -179.09(16) . . . . ?
N8 C4 C3 C2 2.0(3) . . . . ?
N14 N15 C6 N12 0.33(19) . . . . ?
N14 N15 C6 N16 178.62(18) . . . . ?
N19 O2 C10 N18 -0.15(19) . . . . ?
N19 O2 C10 N20 -179.24(15) . . . . ?
N19 C9 C8 N11 175.67(16) . . . . ?
N19 C9 C8 C7 -3.2(3) . . . . ?
N3 N2 N1 C3 178.42(16) . . . . ?
N3 N2 C1 N6 -179.13(16) . . . . ?
N3 N2 C1 N5 0.8(2) . . . . ?
N3 N4 N5 C1 0.6(2) . . . . ?
N4 N5 C1 N2 -0.8(2) . . . . ?
N4 N5 C1 N6 179.11(19) . . . . ?
C9 N18 C10 O2 -0.01(19) . . . . ?
C9 N18 C10 N20 178.95(18) . . . . ?
C4 N9 C5 O1 -0.84(19) . . . . ?
C4 N9 C5 N10 179.25(18) . . . . ?
C4 C3 C2 N7 -0.9(3) . . . . ?
C4 C3 C2 N6 178.93(16) . . . . ?
C5 O1 N8 C4 -0.07(17) . . . . ?
C5 N9 C4 N8 0.8(2) . . . . ?
C5 N9 C4 C3 -179.37(15) . . . . ?
C6 N12 N11 C8 -2.6(2) . . . . ?
C6 N12 N13 N14 0.66(19) . . . . ?
C6 N16 C7 N17 177.44(15) . . . . ?
C6 N16 C7 C8 -0.6(2) . . . . ?
C6 N15 N14 N13 0.1(2) . . . . ?
C10 O2 N19 C9 0.25(17) . . . . ?
C10 N18 C9 N19 0.2(2) . . . . ?
C10 N18 C9 C8 -179.65(15) . . . . ?
C7 N16 C6 N12 -2.8(2) . . . . ?
C7 N16 C6 N15 179.12(18) . . . . ?
C1 N2 N1 C3 1.0(2) . . . . ?
C1 N2 N3 N4 -0.4(2) . . . . ?
C1 N6 C2 N7 179.39(16) . . . . ?
C1 N6 C2 C3 -0.4(2) . . . . ?
C2 N6 C1 N2 1.0(3) . . . . ?
C2 N6 C1 N5 -178.85(19) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
