# Supplementary Information (SI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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_20211241_0m
_database_code_depnum_ccdc_archive 'CCDC 2190888'
loop_
_audit_author_name
_audit_author_address
'Pengju Yang'
;Nanjing University of Science and Technology
China
;
_audit_update_record             
;
2024-08-15 deposited with the CCDC.	2024-08-20 downloaded from the CCDC.
;
_audit_creation_date             2024-08-02
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2019/2
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C6 H4 N10 O3, C3 H7 N O'
_chemical_formula_sum            'C9 H11 N11 O4'
_chemical_formula_weight         337.29
_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           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   34.451(7)
_cell_length_b                   4.6905(10)
_cell_length_c                   20.015(4)
_cell_angle_alpha                90
_cell_angle_beta                 118.803(6)
_cell_angle_gamma                90
_cell_volume                     2834.2(10)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    2243
_cell_measurement_temperature    170
_cell_measurement_theta_max      26.02
_cell_measurement_theta_min      2.32
_shelx_estimated_absorpt_T_max   0.994
_shelx_estimated_absorpt_T_min   0.981
_exptl_absorpt_coefficient_mu    0.129
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6682
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1141 before and 0.0639 after correction.
The Ratio of minimum to maximum transmission is 0.8964.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.581
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1392
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0702
_diffrn_reflns_av_unetI/netI     0.0556
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       42
_diffrn_reflns_limit_h_min       -42
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            13132
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.443
_diffrn_reflns_theta_min         2.322
_diffrn_ambient_temperature      170
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.984
_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                1904
_reflns_number_total             2866
_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 V8.40A (Bruker, 2019)'
_computing_data_collection       'Bruker D8 VENTURE'
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/2 (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.192
_refine_diff_density_min         -0.229
_refine_diff_density_rms         0.047
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     238
_refine_ls_number_reflns         2866
_refine_ls_number_restraints     7
_refine_ls_R_factor_all          0.0904
_refine_ls_R_factor_gt           0.0498
_refine_ls_restrained_S_all      1.077
_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)+(0.0422P)²+1.7135P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1016
_refine_ls_wR_factor_ref         0.1207
_refine_special_details          ?
_olex2_refinement_description    
;
1. Restrained distances
 N11-C10 \\sim N11-C7
 with sigma of 0.02
2. Rigid bond restraints
 C10, C7
 with sigma for 1-2 distances of 0.008 and sigma for 1-3 distances of 0.008
3. Uiso/Uaniso restraints and constraints
C7 \\sim C10: within 2A with sigma of 0.008 and sigma for terminal atoms of
0.016 within 2A
4. Others
 Sof(C10)=Sof(H10A)=Sof(H10B)=Sof(H10C)=1-FVAR(1)
 Sof(C7)=Sof(H7A)=Sof(H7B)=Sof(H7C)=FVAR(1)
5.a Aromatic/amide H refined with riding coordinates:
 C9(H9)
5.b X=CH2 refined with riding coordinates:
 N2(H2A,H2B)
5.c Idealised Me refined as rotating group:
 C8(H8C,H8D,H8E), C7(H7A,H7B,H7C), C10(H10A,H10B,H10C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O4 O 0.48527(5) 0.5538(4) 0.36853(10) 0.0470(5) Uani 1 1 d . . . . .
O3 O 0.36940(6) 0.7935(4) 0.53178(10) 0.0550(5) Uani 1 1 d . . . . .
N6 N 0.36768(6) 0.4008(4) 0.40622(10) 0.0334(5) Uani 1 1 d . . . . .
N5 N 0.33208(6) 0.2219(4) 0.37874(10) 0.0315(4) Uani 1 1 d . . . . .
O1 O 0.23406(6) 0.0794(5) 0.43240(11) 0.0639(6) Uani 1 1 d . . . . .
N7 N 0.36723(6) 0.0998(4) 0.31558(10) 0.0365(5) Uani 1 1 d . . . . .
N2 N 0.30512(6) 0.3871(4) 0.45675(10) 0.0392(5) Uani 1 1 d . . . . .
H2A H 0.327398 0.507819 0.476843 0.047 Uiso 1 1 calc R U . . .
H2B H 0.285463 0.383633 0.472916 0.047 Uiso 1 1 calc R U . . .
N4 N 0.30071(6) -0.1604(4) 0.28889(10) 0.0384(5) Uani 1 1 d . . . . .
O2 O 0.20806(6) -0.2497(5) 0.34640(11) 0.0673(6) Uani 1 1 d . . . . .
N3 N 0.27007(6) -0.1758(4) 0.30972(10) 0.0381(5) Uani 1 1 d . . . . .
N8 N 0.44109(7) 0.8134(5) 0.48012(12) 0.0433(5) Uani 1 1 d . . . . .
N10 N 0.44883(6) 0.3797(5) 0.34188(11) 0.0426(5) Uani 1 1 d . . . . .
N1 N 0.23475(7) -0.0625(5) 0.38052(12) 0.0463(6) Uani 1 1 d . . . . .
N9 N 0.48691(6) 0.7406(5) 0.42502(11) 0.0425(5) Uani 1 1 d . . . . .
N11 N 0.39310(7) 1.0907(5) 0.63305(12) 0.0539(6) Uani 1 1 d D . . . .
C3 C 0.33227(7) 0.0434(5) 0.32417(12) 0.0326(5) Uani 1 1 d . . . . .
C6 C 0.45180(7) 0.6787(5) 0.43157(12) 0.0348(6) Uani 1 1 d . . . . .
C2 C 0.30120(7) 0.2123(5) 0.40278(12) 0.0337(5) Uani 1 1 d . . . . .
C1 C 0.26999(7) -0.0031(5) 0.36293(12) 0.0350(6) Uani 1 1 d . . . . .
C5 C 0.42814(7) 0.4528(5) 0.37919(12) 0.0351(6) Uani 1 1 d . . . . .
C4 C 0.38710(7) 0.3145(5) 0.36598(12) 0.0339(5) Uani 1 1 d . . . . .
C9 C 0.36428(8) 0.9213(6) 0.58091(14) 0.0449(6) Uani 1 1 d . . . . .
H9 H 0.336924 0.894123 0.580784 0.054 Uiso 1 1 calc R U . . .
C8 C 0.38482(11) 1.2313(7) 0.68905(16) 0.0702(9) Uani 1 1 d . . . . .
H8C H 0.354458 1.191010 0.678426 0.105 Uiso 1 1 calc R U . . .
H8D H 0.388634 1.437447 0.686758 0.105 Uiso 1 1 calc R U . . .
H8E H 0.405725 1.160862 0.740010 0.105 Uiso 1 1 calc R U . . .
C7 C 0.4327(2) 1.177(2) 0.6285(5) 0.067(2) Uani 0.712(17) 1 d D U P A 1
H7A H 0.452899 1.014737 0.641094 0.101 Uiso 0.712(17) 1 calc R U P A 1
H7B H 0.447677 1.332713 0.664661 0.101 Uiso 0.712(17) 1 calc R U P A 1
H7C H 0.424033 1.242839 0.576661 0.101 Uiso 0.712(17) 1 calc R U P A 1
H8A H 0.4617(8) 0.941(6) 0.5171(14) 0.050(8) Uiso 1 1 d . . . . .
H8B H 0.4178(9) 0.749(6) 0.4818(14) 0.055(8) Uiso 1 1 d . . . . .
C10 C 0.4423(4) 1.037(6) 0.6626(14) 0.097(5) Uani 0.288(17) 1 d D U P A 2
H10A H 0.456106 0.976675 0.715958 0.146 Uiso 0.288(17) 1 calc R U P A 2
H10B H 0.456463 1.213557 0.658713 0.146 Uiso 0.288(17) 1 calc R U P A 2
H10C H 0.446128 0.888043 0.631954 0.146 Uiso 0.288(17) 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
O4 N10 1.372(3) . ?
O4 N9 1.410(3) . ?
O3 C9 1.235(3) . ?
N6 N5 1.364(2) . ?
N6 C4 1.334(3) . ?
N5 C3 1.379(3) . ?
N5 C2 1.363(3) . ?
O1 N1 1.243(3) . ?
N7 C3 1.323(3) . ?
N7 C4 1.355(3) . ?
N2 H2A 0.8800 . ?
N2 H2B 0.8800 . ?
N2 C2 1.310(3) . ?
N4 N3 1.311(3) . ?
N4 C3 1.362(3) . ?
O2 N1 1.216(3) . ?
N3 C1 1.339(3) . ?
N8 C6 1.351(3) . ?
N8 H8A 0.95(3) . ?
N8 H8B 0.87(3) . ?
N10 C5 1.302(3) . ?
N1 C1 1.445(3) . ?
N9 C6 1.311(3) . ?
N11 C9 1.307(3) . ?
N11 C8 1.442(3) . ?
N11 C7 1.469(5) . ?
N11 C10 1.525(14) . ?
C6 C5 1.436(3) . ?
C2 C1 1.410(3) . ?
C5 C4 1.459(3) . ?
C9 H9 0.9500 . ?
C8 H8C 0.9800 . ?
C8 H8D 0.9800 . ?
C8 H8E 0.9800 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 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
N10 O4 N9 110.95(16) . . ?
C4 N6 N5 100.65(18) . . ?
N6 N5 C3 110.28(18) . . ?
C2 N5 N6 125.50(19) . . ?
C2 N5 C3 124.20(19) . . ?
C3 N7 C4 102.55(19) . . ?
H2A N2 H2B 120.0 . . ?
C2 N2 H2A 120.0 . . ?
C2 N2 H2B 120.0 . . ?
N3 N4 C3 115.96(19) . . ?
N4 N3 C1 122.03(19) . . ?
C6 N8 H8A 119.7(15) . . ?
C6 N8 H8B 116.2(18) . . ?
H8A N8 H8B 123(2) . . ?
C5 N10 O4 105.7(2) . . ?
O1 N1 C1 117.2(2) . . ?
O2 N1 O1 122.8(2) . . ?
O2 N1 C1 120.0(2) . . ?
C6 N9 O4 105.08(18) . . ?
C9 N11 C8 122.7(2) . . ?
C9 N11 C7 119.3(3) . . ?
C9 N11 C10 119.0(8) . . ?
C8 N11 C7 117.4(3) . . ?
C8 N11 C10 112.0(8) . . ?
N7 C3 N5 109.48(19) . . ?
N7 C3 N4 128.5(2) . . ?
N4 C3 N5 122.0(2) . . ?
N8 C6 C5 127.9(2) . . ?
N9 C6 N8 123.6(2) . . ?
N9 C6 C5 108.5(2) . . ?
N5 C2 C1 109.6(2) . . ?
N2 C2 N5 118.9(2) . . ?
N2 C2 C1 131.5(2) . . ?
N3 C1 N1 113.6(2) . . ?
N3 C1 C2 126.2(2) . . ?
C2 C1 N1 120.1(2) . . ?
N10 C5 C6 109.8(2) . . ?
N10 C5 C4 122.0(2) . . ?
C6 C5 C4 128.3(2) . . ?
N6 C4 N7 117.0(2) . . ?
N6 C4 C5 118.7(2) . . ?
N7 C4 C5 124.3(2) . . ?
O3 C9 N11 125.9(2) . . ?
O3 C9 H9 117.1 . . ?
N11 C9 H9 117.1 . . ?
N11 C8 H8C 109.5 . . ?
N11 C8 H8D 109.5 . . ?
N11 C8 H8E 109.5 . . ?
H8C C8 H8D 109.5 . . ?
H8C C8 H8E 109.5 . . ?
H8D C8 H8E 109.5 . . ?
N11 C7 H7A 109.5 . . ?
N11 C7 H7B 109.5 . . ?
N11 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N11 C10 H10A 109.5 . . ?
N11 C10 H10B 109.5 . . ?
N11 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 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
O4 N10 C5 C6 -0.3(2) . . . . ?
O4 N10 C5 C4 179.60(19) . . . . ?
O4 N9 C6 N8 -179.6(2) . . . . ?
O4 N9 C6 C5 0.0(2) . . . . ?
N6 N5 C3 N7 0.4(2) . . . . ?
N6 N5 C3 N4 178.56(19) . . . . ?
N6 N5 C2 N2 0.0(3) . . . . ?
N6 N5 C2 C1 -178.54(19) . . . . ?
N5 N6 C4 N7 0.3(2) . . . . ?
N5 N6 C4 C5 -179.08(18) . . . . ?
N5 C2 C1 N3 0.4(3) . . . . ?
N5 C2 C1 N1 177.6(2) . . . . ?
O1 N1 C1 N3 176.2(2) . . . . ?
O1 N1 C1 C2 -1.4(3) . . . . ?
N2 C2 C1 N3 -177.9(2) . . . . ?
N2 C2 C1 N1 -0.7(4) . . . . ?
N4 N3 C1 N1 -177.2(2) . . . . ?
N4 N3 C1 C2 0.2(4) . . . . ?
O2 N1 C1 N3 -1.9(3) . . . . ?
O2 N1 C1 C2 -179.5(2) . . . . ?
N3 N4 C3 N5 0.3(3) . . . . ?
N3 N4 C3 N7 178.1(2) . . . . ?
N8 C6 C5 N10 179.7(2) . . . . ?
N8 C6 C5 C4 -0.1(4) . . . . ?
N10 O4 N9 C6 -0.2(2) . . . . ?
N10 C5 C4 N6 -179.9(2) . . . . ?
N10 C5 C4 N7 0.8(3) . . . . ?
N9 O4 N10 C5 0.3(2) . . . . ?
N9 C6 C5 N10 0.2(3) . . . . ?
N9 C6 C5 C4 -179.7(2) . . . . ?
C3 N5 C2 N2 177.9(2) . . . . ?
C3 N5 C2 C1 -0.6(3) . . . . ?
C3 N7 C4 N6 -0.1(3) . . . . ?
C3 N7 C4 C5 179.3(2) . . . . ?
C3 N4 N3 C1 -0.5(3) . . . . ?
C6 C5 C4 N6 0.0(3) . . . . ?
C6 C5 C4 N7 -179.4(2) . . . . ?
C2 N5 C3 N7 -177.8(2) . . . . ?
C2 N5 C3 N4 0.4(3) . . . . ?
C4 N6 N5 C3 -0.4(2) . . . . ?
C4 N6 N5 C2 177.8(2) . . . . ?
C4 N7 C3 N5 -0.2(2) . . . . ?
C4 N7 C3 N4 -178.2(2) . . . . ?
C8 N11 C9 O3 -179.5(3) . . . . ?
C7 N11 C9 O3 9.9(6) . . . . ?
C10 N11 C9 O3 -29.8(14) . . . . ?


_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_1
_database_code_depnum_ccdc_archive 'CCDC 2254742'
loop_
_audit_author_name
_audit_author_address
ypj
;Nanjing University of Science and Technology
China
;
_audit_update_record             
;
2023-04-07 deposited with the CCDC.	2024-08-20 downloaded from the CCDC.
;
_audit_creation_date             2022-05-24
_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         'C7 H4 N10 O4'
_chemical_formula_sum            'C7 H4 N10 O4'
_chemical_formula_weight         292.20
_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'
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      orthorhombic
_space_group_IT_number           60
_space_group_name_H-M_alt        'P b c n'
_space_group_name_Hall           '-P 2n 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y+1/2, z+1/2'
'-x, y, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'x, -y, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   15.467(3)
_cell_length_b                   6.7622(7)
_cell_length_c                   20.528(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2147.0(5)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    153
_cell_measurement_temperature    193.00
_cell_measurement_theta_max      39.791
_cell_measurement_theta_min      12.302
_shelx_estimated_absorpt_T_max   0.878
_shelx_estimated_absorpt_T_min   0.846
_exptl_absorpt_coefficient_mu    1.333
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.5349
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1744 before and 0.0574 after correction.
The Ratio of minimum to maximum transmission is 0.7103.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.808
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1184
_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  0.0511
_diffrn_reflns_av_unetI/netI     0.0471
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            8252
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.386
_diffrn_reflns_theta_min         4.307
_diffrn_ambient_temperature      193.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.992
_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                1578
_reflns_number_total             1956
_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         0.296
_refine_diff_density_min         -0.306
_refine_diff_density_rms         0.079
_refine_ls_extinction_coef       0.0018(4)
_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   1.033
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     195
_refine_ls_number_reflns         1956
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0578
_refine_ls_R_factor_gt           0.0460
_refine_ls_restrained_S_all      1.033
_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)+(0.0870P)²+0.0501P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1166
_refine_ls_wR_factor_ref         0.1266
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C6(H6)
2.b X=CH2 refined with riding coordinates:
 N5(H5A,H5B)
;
_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
O1 O 0.36829(11) 0.4641(2) 0.19449(7) 0.0320(4) Uani 1 1 d . . . . .
O2 O 0.29775(13) 0.7276(2) 0.21977(8) 0.0420(5) Uani 1 1 d . . . . .
O3 O 0.48778(11) 0.3718(2) 0.59143(8) 0.0312(4) Uani 1 1 d . . . . .
O4 O 0.50390(11) 0.2031(2) 0.68034(7) 0.0314(4) Uani 1 1 d . . . . .
N1 N 0.33287(12) 0.5738(2) 0.23442(9) 0.0239(4) Uani 1 1 d . . . . .
N2 N 0.30522(11) 0.6466(2) 0.34269(8) 0.0220(4) Uani 1 1 d . . . . .
N3 N 0.30523(11) 0.6187(2) 0.40623(8) 0.0218(4) Uani 1 1 d . . . . .
N4 N 0.37038(10) 0.3044(2) 0.38545(8) 0.0177(4) Uani 1 1 d . . . . .
N5 N 0.40157(12) 0.1814(2) 0.28305(8) 0.0243(4) Uani 1 1 d . . . . .
H5A H 0.420690 0.072338 0.301503 0.029 Uiso 1 1 calc R U . . .
H5B H 0.402631 0.193427 0.240372 0.029 Uiso 1 1 calc R U . . .
N6 N 0.39680(11) 0.1430(2) 0.41904(8) 0.0197(4) Uani 1 1 d . . . . .
N7 N 0.34659(12) 0.3831(2) 0.48805(8) 0.0209(4) Uani 1 1 d . . . . .
N8 N 0.37602(13) -0.2178(3) 0.58835(9) 0.0270(4) Uani 1 1 d . . . . .
H8 H 0.3666(19) -0.337(4) 0.5993(13) 0.037(7) Uiso 1 1 d . . . . .
N9 N 0.41566(12) -0.0978(2) 0.63071(8) 0.0232(4) Uani 1 1 d . . . . .
N10 N 0.47480(12) 0.2251(2) 0.62498(8) 0.0225(4) Uani 1 1 d . . . . .
C1 C 0.33660(13) 0.5126(3) 0.30187(9) 0.0195(4) Uani 1 1 d . . . . .
C2 C 0.37152(12) 0.3258(3) 0.31914(10) 0.0187(4) Uani 1 1 d . . . . .
C3 C 0.33939(13) 0.4460(3) 0.42721(10) 0.0185(4) Uani 1 1 d . . . . .
C4 C 0.38079(13) 0.1997(3) 0.48039(10) 0.0192(4) Uani 1 1 d . . . . .
C5 C 0.39106(13) 0.0565(3) 0.53348(9) 0.0207(4) Uani 1 1 d . . . . .
C6 C 0.36061(15) -0.1336(3) 0.53047(10) 0.0263(5) Uani 1 1 d . . . . .
H6 H 0.333569 -0.194420 0.494057 0.032 Uiso 1 1 calc R U . . .
C7 C 0.42470(13) 0.0683(3) 0.59691(10) 0.0197(4) 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
O1 N1 1.234(2) . ?
O2 N1 1.211(2) . ?
O3 N10 1.224(2) . ?
O4 N10 1.231(2) . ?
N1 C1 1.446(3) . ?
N2 N3 1.318(2) . ?
N2 C1 1.326(3) . ?
N3 C3 1.352(2) . ?
N4 N6 1.354(2) . ?
N4 C2 1.369(3) . ?
N4 C3 1.372(2) . ?
N5 H5A 0.8800 . ?
N5 H5B 0.8800 . ?
N5 C2 1.311(3) . ?
N6 C4 1.340(3) . ?
N7 C3 1.324(3) . ?
N7 C4 1.358(3) . ?
N8 H8 0.85(3) . ?
N8 N9 1.338(3) . ?
N8 C6 1.339(3) . ?
N9 C7 1.328(3) . ?
N10 C7 1.434(3) . ?
C1 C2 1.419(3) . ?
C4 C5 1.466(3) . ?
C5 C6 1.371(3) . ?
C5 C7 1.404(3) . ?
C6 H6 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
O1 N1 C1 116.49(16) . . ?
O2 N1 O1 123.40(18) . . ?
O2 N1 C1 120.09(17) . . ?
N3 N2 C1 121.83(16) . . ?
N2 N3 C3 116.03(16) . . ?
N6 N4 C2 125.99(16) . . ?
N6 N4 C3 110.49(15) . . ?
C2 N4 C3 123.51(16) . . ?
H5A N5 H5B 120.0 . . ?
C2 N5 H5A 120.0 . . ?
C2 N5 H5B 120.0 . . ?
C4 N6 N4 101.08(15) . . ?
C3 N7 C4 102.56(16) . . ?
N9 N8 H8 118.8(19) . . ?
N9 N8 C6 113.61(17) . . ?
C6 N8 H8 127.4(19) . . ?
C7 N9 N8 102.81(16) . . ?
O3 N10 O4 123.87(17) . . ?
O3 N10 C7 117.50(16) . . ?
O4 N10 C7 118.61(17) . . ?
N2 C1 N1 113.24(17) . . ?
N2 C1 C2 126.16(18) . . ?
C2 C1 N1 120.61(17) . . ?
N4 C2 C1 109.73(17) . . ?
N5 C2 N4 119.18(17) . . ?
N5 C2 C1 131.08(19) . . ?
N3 C3 N4 122.71(18) . . ?
N7 C3 N3 127.66(17) . . ?
N7 C3 N4 109.60(16) . . ?
N6 C4 N7 116.26(17) . . ?
N6 C4 C5 119.33(16) . . ?
N7 C4 C5 124.01(18) . . ?
C6 C5 C4 123.26(18) . . ?
C6 C5 C7 102.85(17) . . ?
C7 C5 C4 133.77(18) . . ?
N8 C6 C5 107.32(18) . . ?
N8 C6 H6 126.3 . . ?
C5 C6 H6 126.3 . . ?
N9 C7 N10 118.20(18) . . ?
N9 C7 C5 113.41(17) . . ?
C5 C7 N10 127.93(17) . . ?

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 173.48(18) . . . . ?
O1 N1 C1 C2 -6.3(3) . . . . ?
O2 N1 C1 N2 -5.1(3) . . . . ?
O2 N1 C1 C2 175.1(2) . . . . ?
O3 N10 C7 N9 174.89(18) . . . . ?
O3 N10 C7 C5 3.2(3) . . . . ?
O4 N10 C7 N9 -3.4(3) . . . . ?
O4 N10 C7 C5 -175.0(2) . . . . ?
N1 C1 C2 N4 178.20(17) . . . . ?
N1 C1 C2 N5 -2.5(3) . . . . ?
N2 N3 C3 N4 -1.7(3) . . . . ?
N2 N3 C3 N7 -179.70(19) . . . . ?
N2 C1 C2 N4 -1.6(3) . . . . ?
N2 C1 C2 N5 177.7(2) . . . . ?
N3 N2 C1 N1 -178.31(17) . . . . ?
N3 N2 C1 C2 1.5(3) . . . . ?
N4 N6 C4 N7 0.0(2) . . . . ?
N4 N6 C4 C5 172.96(17) . . . . ?
N6 N4 C2 N5 -1.0(3) . . . . ?
N6 N4 C2 C1 178.33(17) . . . . ?
N6 N4 C3 N3 -176.96(17) . . . . ?
N6 N4 C3 N7 1.4(2) . . . . ?
N6 C4 C5 C6 -44.9(3) . . . . ?
N6 C4 C5 C7 139.7(2) . . . . ?
N7 C4 C5 C6 127.5(2) . . . . ?
N7 C4 C5 C7 -47.8(4) . . . . ?
N8 N9 C7 N10 -172.61(17) . . . . ?
N8 N9 C7 C5 0.2(2) . . . . ?
N9 N8 C6 C5 -0.4(3) . . . . ?
C1 N2 N3 C3 0.3(3) . . . . ?
C2 N4 N6 C4 -179.23(18) . . . . ?
C2 N4 C3 N3 1.5(3) . . . . ?
C2 N4 C3 N7 179.86(18) . . . . ?
C3 N4 N6 C4 -0.8(2) . . . . ?
C3 N4 C2 N5 -179.28(18) . . . . ?
C3 N4 C2 C1 0.1(3) . . . . ?
C3 N7 C4 N6 0.8(2) . . . . ?
C3 N7 C4 C5 -171.79(19) . . . . ?
C4 N7 C3 N3 177.0(2) . . . . ?
C4 N7 C3 N4 -1.3(2) . . . . ?
C4 C5 C6 N8 -176.0(2) . . . . ?
C4 C5 C7 N9 175.5(2) . . . . ?
C4 C5 C7 N10 -12.5(4) . . . . ?
C6 N8 N9 C7 0.1(2) . . . . ?
C6 C5 C7 N9 -0.5(2) . . . . ?
C6 C5 C7 N10 171.5(2) . . . . ?
C7 C5 C6 N8 0.5(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_mo_2021771_0m
_database_code_depnum_ccdc_archive 'CCDC 2190890'
loop_
_audit_author_name
_audit_author_address
'Pengju Yang'
;Nanjing University of Science and Technology
China
;
_audit_update_record             
;
2022-07-18 deposited with the CCDC.	2024-08-20 downloaded from the CCDC.
;
_audit_creation_date             2021-06-03
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(H2 O), C6 H3 N11 O4'
_chemical_formula_sum            'C6 H7 N11 O6'
_chemical_formula_weight         329.23
_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                   9.966(2)
_cell_length_b                   13.360(3)
_cell_length_c                   18.602(4)
_cell_angle_alpha                90
_cell_angle_beta                 94.827(7)
_cell_angle_gamma                90
_cell_volume                     2467.9(9)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    1990
_cell_measurement_temperature    170
_cell_measurement_theta_max      24.601
_cell_measurement_theta_min      2.24
_shelx_estimated_absorpt_T_max   0.997
_shelx_estimated_absorpt_T_min   0.983
_exptl_absorpt_coefficient_mu    0.157
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6620
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0759 before and 0.0668 after correction. The Ratio of minimum to maximum transmission is 0.8884. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.772
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1344
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0951
_diffrn_reflns_av_unetI/netI     0.0877
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            19352
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.381
_diffrn_reflns_theta_min         2.197
_diffrn_ambient_temperature      170.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  'D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2440
_reflns_number_total             4448
_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 V8.40A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.293
_refine_diff_density_min         -0.347
_refine_diff_density_rms         0.071
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     435
_refine_ls_number_reflns         4448
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1306
_refine_ls_R_factor_gt           0.0601
_refine_ls_restrained_S_all      1.009
_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)+(0.0695P)²+0.0485P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1241
_refine_ls_wR_factor_ref         0.1609
_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 O(H,H) groups
2.a Free rotating group:
 O3(H3A,H3B), O9(H9A,H9B), O10(H10A,H10B), O8(H8A,H8B)
2.b X=CH2 refined with riding coordinates:
 N22(H22A,H22B), N6(H6A,H6B)
;
_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
O3 O 0.5380(3) 0.8309(2) 0.46456(15) 0.0404(8) Uani 1 1 d . . . . .
H3A H 0.592839 0.881424 0.463867 0.061 Uiso 1 1 d G . . . .
H3B H 0.490400 0.826657 0.423271 0.061 Uiso 1 1 d G . . . .
O9 O 0.8451(3) -0.1260(2) 0.60350(15) 0.0380(7) Uani 1 1 d . . . . .
H9A H 0.916096 -0.129191 0.633978 0.057 Uiso 1 1 d G . . . .
H9B H 0.824088 -0.185802 0.587816 0.057 Uiso 1 1 d G . . . .
O12 O 0.0361(3) 0.1577(2) 0.14495(15) 0.0402(8) Uani 1 1 d . . . . .
O4 O 0.7998(3) 0.3727(2) 0.58067(15) 0.0402(8) Uani 1 1 d . . . . .
O11 O 0.1428(3) 0.2979(2) 0.16198(15) 0.0395(7) Uani 1 1 d . . . . .
O10 O 0.5290(3) 0.4415(2) 0.34133(16) 0.0419(8) Uani 1 1 d . . . . .
H10A H 0.568278 0.432737 0.384401 0.063 Uiso 1 1 d G . . . .
H10B H 0.480966 0.495967 0.340506 0.063 Uiso 1 1 d G . . . .
O6 O 0.9240(3) 0.2931(2) 0.45761(15) 0.0419(8) Uani 1 1 d . . . . .
O5 O 0.6550(3) 0.3734(2) 0.48626(16) 0.0430(8) Uani 1 1 d . . . . .
O2 O 1.4196(3) 0.4068(2) 0.80002(15) 0.0399(7) Uani 1 1 d . . . . .
O7 O 0.7704(3) 0.2782(2) 0.36822(16) 0.0432(8) Uani 1 1 d . . . . .
N18 N 0.4070(3) 0.1604(2) 0.30816(16) 0.0286(8) Uani 1 1 d . . . . .
N4 N 1.0872(3) 0.5336(2) 0.69560(16) 0.0297(8) Uani 1 1 d . . . . .
O1 O 1.4578(3) 0.5462(2) 0.85782(17) 0.0525(9) Uani 1 1 d . . . . .
N16 N 0.5167(3) 0.1916(2) 0.35071(17) 0.0301(8) Uani 1 1 d . . . . .
N20 N 0.2061(3) 0.0641(2) 0.23402(17) 0.0318(8) Uani 1 1 d . . . . .
N5 N 0.9966(3) 0.5033(2) 0.64103(17) 0.0323(8) Uani 1 1 d . . . . .
N17 N 0.4856(3) 0.0210(2) 0.35905(17) 0.0325(8) Uani 1 1 d . . . . .
N9 N 0.6619(4) 0.6653(3) 0.50881(19) 0.0377(9) Uani 1 1 d . . . . .
N8 N 0.7571(3) 0.6811(3) 0.56149(17) 0.0349(9) Uani 1 1 d . . . . .
N21 N 0.1262(4) 0.2081(3) 0.17531(18) 0.0354(9) Uani 1 1 d . . . . .
N22 N 0.3494(3) 0.3164(2) 0.26333(17) 0.0337(8) Uani 1 1 d . . . . .
H22A H 0.418318 0.341295 0.290227 0.040 Uiso 1 1 calc R . . . .
H22B H 0.297260 0.356132 0.235537 0.040 Uiso 1 1 calc R . . . .
N7 N 0.9471(3) 0.6602(3) 0.68155(17) 0.0344(9) Uani 1 1 d . . . . .
N1 N 1.3896(3) 0.4949(3) 0.81376(18) 0.0343(9) Uani 1 1 d . . . . .
N15 N 0.6902(3) 0.0129(3) 0.47237(18) 0.0357(9) Uani 1 1 d . . . . .
N12 N 0.8307(4) 0.2490(3) 0.42422(18) 0.0357(9) Uani 1 1 d . . . . .
N6 N 1.2149(3) 0.3901(3) 0.69780(18) 0.0364(9) Uani 1 1 d . . . . .
H6A H 1.158467 0.365793 0.663239 0.044 Uiso 1 1 calc R . . . .
H6B H 1.284296 0.354199 0.715089 0.044 Uiso 1 1 calc R . . . .
N10 N 0.6403(3) 0.5713(3) 0.49038(18) 0.0354(9) Uani 1 1 d . . . . .
N3 N 1.1339(3) 0.6762(3) 0.77149(18) 0.0347(8) Uani 1 1 d . . . . .
N2 N 1.2402(3) 0.6278(3) 0.79878(17) 0.0346(9) Uani 1 1 d . . . . .
N19 N 0.2870(3) 0.0091(2) 0.27636(17) 0.0329(8) Uani 1 1 d . . . . .
N11 N 0.7288(4) 0.4153(3) 0.53372(19) 0.0359(9) Uani 1 1 d . . . . .
N13 N 0.8668(4) 0.1105(3) 0.50442(18) 0.0382(9) Uani 1 1 d . . . . .
N14 N 0.8018(4) 0.0265(3) 0.5139(2) 0.0394(9) Uani 1 1 d . . . . .
O8 O 1.0953(4) 0.2638(3) 0.5978(2) 0.0757(12) Uani 1 1 d . . . . .
H8A H 1.113350 0.203708 0.613825 0.114 Uiso 1 1 d G . . . .
H8B H 1.021415 0.262689 0.569292 0.114 Uiso 1 1 d G . . . .
C9 C 0.5591(4) 0.1041(3) 0.3797(2) 0.0286(9) Uani 1 1 d . . . . .
C2 C 1.1958(4) 0.4789(3) 0.7233(2) 0.0306(10) Uani 1 1 d . . . . .
C3 C 1.0567(4) 0.6288(3) 0.7189(2) 0.0309(10) Uani 1 1 d . . . . .
C5 C 0.8029(4) 0.5897(3) 0.5799(2) 0.0299(9) Uani 1 1 d . . . . .
C4 C 0.9158(4) 0.5826(3) 0.6352(2) 0.0294(9) Uani 1 1 d . . . . .
C10 C 0.3895(4) 0.0585(3) 0.3139(2) 0.0286(10) Uani 1 1 d . . . . .
C12 C 0.2225(4) 0.1631(3) 0.2279(2) 0.0310(10) Uani 1 1 d . . . . .
C11 C 0.3249(4) 0.2212(3) 0.2646(2) 0.0294(9) Uani 1 1 d . . . . .
C8 C 0.6772(4) 0.0952(3) 0.4315(2) 0.0309(10) Uani 1 1 d . . . . .
C1 C 1.2699(4) 0.5355(3) 0.7774(2) 0.0323(10) Uani 1 1 d . . . . .
C6 C 0.7282(4) 0.5238(3) 0.5354(2) 0.0325(10) Uani 1 1 d . . . . .
C7 C 0.7891(4) 0.1541(3) 0.4525(2) 0.0309(10) Uani 1 1 d . . . . .
H9 H 0.620(4) 0.719(3) 0.487(2) 0.036(12) Uiso 1 1 d . . . . .
H14 H 0.835(5) -0.020(4) 0.545(2) 0.060(16) 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
O3 H3A 0.8700 . ?
O3 H3B 0.8698 . ?
O9 H9A 0.8699 . ?
O9 H9B 0.8700 . ?
O12 N21 1.222(4) . ?
O4 N11 1.217(4) . ?
O11 N21 1.239(4) . ?
O10 H10A 0.8695 . ?
O10 H10B 0.8700 . ?
O6 N12 1.225(4) . ?
O5 N11 1.234(4) . ?
O2 N1 1.247(4) . ?
O7 N12 1.222(4) . ?
N18 N16 1.359(4) . ?
N18 C10 1.378(5) . ?
N18 C11 1.369(5) . ?
N4 N5 1.362(4) . ?
N4 C2 1.370(5) . ?
N4 C3 1.385(5) . ?
O1 N1 1.229(4) . ?
N16 C9 1.340(5) . ?
N20 N19 1.305(4) . ?
N20 C12 1.339(5) . ?
N5 C4 1.329(5) . ?
N17 C9 1.368(5) . ?
N17 C10 1.319(5) . ?
N9 N8 1.322(5) . ?
N9 N10 1.315(5) . ?
N9 H9 0.92(4) . ?
N8 C5 1.338(5) . ?
N21 C12 1.442(5) . ?
N22 H22A 0.8800 . ?
N22 H22B 0.8800 . ?
N22 C11 1.296(5) . ?
N7 C3 1.314(5) . ?
N7 C4 1.368(5) . ?
N1 C1 1.428(5) . ?
N15 N14 1.312(5) . ?
N15 C8 1.337(5) . ?
N12 C7 1.446(5) . ?
N6 H6A 0.8800 . ?
N6 H6B 0.8800 . ?
N6 C2 1.297(5) . ?
N10 C6 1.322(5) . ?
N3 N2 1.307(4) . ?
N3 C3 1.350(5) . ?
N2 C1 1.336(5) . ?
N19 C10 1.359(5) . ?
N11 C6 1.451(5) . ?
N13 N14 1.315(5) . ?
N13 C7 1.321(5) . ?
N14 H14 0.90(5) . ?
O8 H8A 0.8701 . ?
O8 H8B 0.8700 . ?
C9 C8 1.461(5) . ?
C2 C1 1.416(6) . ?
C5 C4 1.462(5) . ?
C5 C6 1.383(5) . ?
C12 C11 1.413(5) . ?
C8 C7 1.394(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
H3A O3 H3B 109.5 . . ?
H9A O9 H9B 109.5 . . ?
H10A O10 H10B 109.5 . . ?
N16 N18 C10 111.0(3) . . ?
N16 N18 C11 125.0(3) . . ?
C11 N18 C10 124.0(3) . . ?
N5 N4 C2 125.1(3) . . ?
N5 N4 C3 110.9(3) . . ?
C2 N4 C3 124.0(3) . . ?
C9 N16 N18 100.3(3) . . ?
N19 N20 C12 122.3(3) . . ?
C4 N5 N4 100.6(3) . . ?
C10 N17 C9 102.3(3) . . ?
N8 N9 H9 119(3) . . ?
N10 N9 N8 115.9(4) . . ?
N10 N9 H9 125(3) . . ?
N9 N8 C5 104.7(3) . . ?
O12 N21 O11 123.1(3) . . ?
O12 N21 C12 120.3(3) . . ?
O11 N21 C12 116.6(3) . . ?
H22A N22 H22B 120.0 . . ?
C11 N22 H22A 120.0 . . ?
C11 N22 H22B 120.0 . . ?
C3 N7 C4 103.0(3) . . ?
O2 N1 C1 117.8(3) . . ?
O1 N1 O2 122.3(3) . . ?
O1 N1 C1 119.8(4) . . ?
N14 N15 C8 104.9(3) . . ?
O6 N12 C7 117.8(3) . . ?
O7 N12 O6 125.2(4) . . ?
O7 N12 C7 117.0(3) . . ?
H6A N6 H6B 120.0 . . ?
C2 N6 H6A 120.0 . . ?
C2 N6 H6B 120.0 . . ?
N9 N10 C6 102.0(3) . . ?
N2 N3 C3 116.3(3) . . ?
N3 N2 C1 122.2(3) . . ?
N20 N19 C10 115.9(3) . . ?
O4 N11 O5 125.2(4) . . ?
O4 N11 C6 117.0(3) . . ?
O5 N11 C6 117.7(3) . . ?
N14 N13 C7 102.1(4) . . ?
N15 N14 N13 116.2(4) . . ?
N15 N14 H14 122(3) . . ?
N13 N14 H14 121(3) . . ?
H8A O8 H8B 109.5 . . ?
N16 C9 N17 116.8(4) . . ?
N16 C9 C8 123.1(4) . . ?
N17 C9 C8 120.1(4) . . ?
N4 C2 C1 109.3(4) . . ?
N6 C2 N4 119.1(4) . . ?
N6 C2 C1 131.6(4) . . ?
N7 C3 N4 108.8(3) . . ?
N7 C3 N3 129.1(4) . . ?
N3 C3 N4 122.1(4) . . ?
N8 C5 C4 117.8(4) . . ?
N8 C5 C6 105.8(3) . . ?
C6 C5 C4 136.4(4) . . ?
N5 C4 N7 116.6(4) . . ?
N5 C4 C5 122.3(4) . . ?
N7 C4 C5 121.0(4) . . ?
N17 C10 N18 109.6(3) . . ?
N17 C10 N19 128.1(4) . . ?
N19 C10 N18 122.3(4) . . ?
N20 C12 N21 113.0(3) . . ?
N20 C12 C11 126.2(4) . . ?
C11 C12 N21 120.7(4) . . ?
N18 C11 C12 109.4(4) . . ?
N22 C11 N18 119.3(4) . . ?
N22 C11 C12 131.3(4) . . ?
N15 C8 C9 118.4(4) . . ?
N15 C8 C7 105.5(3) . . ?
C7 C8 C9 136.1(4) . . ?
N2 C1 N1 114.0(4) . . ?
N2 C1 C2 126.1(4) . . ?
C2 C1 N1 119.9(4) . . ?
N10 C6 N11 118.0(4) . . ?
N10 C6 C5 111.6(4) . . ?
C5 C6 N11 130.3(4) . . ?
N13 C7 N12 119.0(4) . . ?
N13 C7 C8 111.2(4) . . ?
C8 C7 N12 129.8(4) . . ?


_olex2_submission_special_instructions 'No special instructions were received'
