# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_bwn18298
_database_code_depnum_ccdc_archive 'CCDC 2005504'
_audit_update_record             
;
2020-05-24 deposited with the CCDC.	2021-04-28 downloaded from the CCDC.
;
_audit_creation_date             2018-10-11
_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(Cl), C3 H9 N5'
_chemical_formula_sum            'C3 H9 Cl2 N5'
_chemical_formula_weight         186.05
_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'
Cl Cl 0.1484 0.1585 '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'

_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                   5.1549(10)
_cell_length_b                   6.9133(14)
_cell_length_c                   11.867(2)
_cell_angle_alpha                74.96(3)
_cell_angle_beta                 80.75(3)
_cell_angle_gamma                88.14(3)
_cell_volume                     403.10(15)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1414
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.4739
_cell_measurement_theta_min      3.0512
_shelx_estimated_absorpt_T_max   0.943
_shelx_estimated_absorpt_T_min   0.910
_exptl_absorpt_coefficient_mu    0.741
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8043
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2008)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.533
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             192
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0326
_diffrn_reflns_av_unetI/netI     0.0386
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            3564
_diffrn_reflns_point_group_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.493
_diffrn_reflns_theta_min         1.799
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1699
_reflns_number_total             1803
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_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         0.394
_refine_diff_density_min         -0.326
_refine_diff_density_rms         0.074
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.105
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     91
_refine_ls_number_reflns         1803
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0371
_refine_ls_R_factor_gt           0.0344
_refine_ls_restrained_S_all      1.105
_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)+(0.0323P)²+0.3560P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0841
_refine_ls_wR_factor_ref         0.0874
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups, All N(H,H) groups, All N(H,H,H) groups
2.a Riding coordinates:
 N1(H1), N2(H2), N5(H5A,H5B), N4(H4A,H4B,H4C), N3(H3)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2A)
;
_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
Cl2 Cl 0.81481(9) 0.20936(6) 0.14219(4) 0.01818(14) Uani 1 1 d . . . . .
Cl1 Cl -0.26654(9) 0.23224(6) 0.47375(4) 0.01892(14) Uani 1 1 d . . . . .
N1 N 0.3791(3) 0.5321(2) 0.14759(14) 0.0186(3) Uani 1 1 d . . . . .
H1 H 0.486000 0.435320 0.150410 0.022 Uiso 1 1 d R . . . .
N2 N 0.1596(3) 0.4921(2) 0.23663(15) 0.0193(3) Uani 1 1 d . . . . .
H2 H 0.048504 0.404871 0.235232 0.023 Uiso 1 1 d R . . . .
N5 N 0.6803(3) 0.7983(3) 0.06364(15) 0.0218(4) Uani 1 1 d . . . . .
H5A H 0.740416 0.910412 0.065221 0.026 Uiso 1 1 d R . . . .
H5B H 0.782696 0.738722 0.020201 0.026 Uiso 1 1 d R . . . .
N4 N -0.1837(3) 0.8537(2) 0.37483(14) 0.0175(3) Uani 1 1 d . . . . .
H4A H -0.061201 0.860456 0.413871 0.021 Uiso 1 1 d R . . . .
H4B H -0.179231 0.958626 0.318101 0.021 Uiso 1 1 d R . . . .
H4C H -0.340081 0.844376 0.411931 0.021 Uiso 1 1 d R . . . .
C2 C 0.2742(4) 0.8156(3) 0.20250(16) 0.0161(4) Uani 1 1 d . . . . .
H2A H 0.276183 0.950539 0.207405 0.019 Uiso 1 1 calc R . . . .
C1 C 0.4589(4) 0.7226(3) 0.13367(16) 0.0159(4) Uani 1 1 d . . . . .
N3 N -0.1495(3) 0.6796(2) 0.33009(14) 0.0173(3) Uani 1 1 d . . . . .
H3 H -0.206161 0.571883 0.380220 0.021 Uiso 1 1 d R . . . .
C3 C 0.0889(4) 0.6692(3) 0.26161(16) 0.0147(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
N1 H1 0.8500 . ?
N1 N2 1.399(2) . ?
N1 C1 1.354(2) . ?
N2 H2 0.8500 . ?
N2 C3 1.358(2) . ?
N5 H5A 0.8500 . ?
N5 H5B 0.8499 . ?
N5 C1 1.332(2) . ?
N4 H4A 0.8500 . ?
N4 H4B 0.8500 . ?
N4 H4C 0.8500 . ?
N4 N3 1.432(2) . ?
C2 H2A 0.9500 . ?
C2 C1 1.403(3) . ?
C2 C3 1.381(3) . ?
N3 H3 0.8500 . ?
N3 C3 1.371(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
N2 N1 H1 113.9 . . ?
C1 N1 H1 122.4 . . ?
C1 N1 N2 107.93(15) . . ?
N1 N2 H2 118.4 . . ?
C3 N2 N1 106.64(15) . . ?
C3 N2 H2 123.0 . . ?
H5A N5 H5B 113.3 . . ?
C1 N5 H5A 120.5 . . ?
C1 N5 H5B 125.8 . . ?
H4A N4 H4B 109.1 . . ?
H4A N4 H4C 117.0 . . ?
H4B N4 H4C 105.9 . . ?
N3 N4 H4A 109.5 . . ?
N3 N4 H4B 110.1 . . ?
N3 N4 H4C 105.0 . . ?
C1 C2 H2A 127.3 . . ?
C3 C2 H2A 127.3 . . ?
C3 C2 C1 105.34(16) . . ?
N1 C1 C2 109.01(16) . . ?
N5 C1 N1 122.15(17) . . ?
N5 C1 C2 128.84(18) . . ?
N4 N3 H3 114.0 . . ?
C3 N3 N4 114.78(15) . . ?
C3 N3 H3 116.3 . . ?
N2 C3 C2 110.32(16) . . ?
N2 C3 N3 118.38(16) . . ?
N3 C3 C2 131.11(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
N1 N2 C3 C2 -7.5(2) . . . . ?
N1 N2 C3 N3 167.99(16) . . . . ?
N2 N1 C1 N5 172.93(18) . . . . ?
N2 N1 C1 C2 -7.3(2) . . . . ?
N4 N3 C3 N2 166.24(16) . . . . ?
N4 N3 C3 C2 -19.4(3) . . . . ?
C1 N1 N2 C3 9.0(2) . . . . ?
C1 C2 C3 N2 3.1(2) . . . . ?
C1 C2 C3 N3 -171.6(2) . . . . ?
C3 C2 C1 N1 2.7(2) . . . . ?
C3 C2 C1 N5 -177.5(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_bwn18399_tw
_database_code_depnum_ccdc_archive 'CCDC 2005505'
_audit_update_record             
;
2020-05-24 deposited with the CCDC.	2021-04-28 downloaded from the CCDC.
;
_audit_creation_date             2018-11-13
_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(N O3), C3 H9 N5'
_chemical_formula_sum            'C3 H9 N7 O6'
_chemical_formula_weight         239.17
_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/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   6.6631(13)
_cell_length_b                   9.3281(19)
_cell_length_c                   14.077(3)
_cell_angle_alpha                90
_cell_angle_beta                 93.39(3)
_cell_angle_gamma                90
_cell_volume                     873.4(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2588
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      27.4816
_cell_measurement_theta_min      1.4491
_shelx_estimated_absorpt_T_max   0.967
_shelx_estimated_absorpt_T_min   0.962
_exptl_absorpt_coefficient_mu    0.171
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8243
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2008)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.819
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             496
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_av_unetI/netI     0.0360
_diffrn_reflns_Laue_measured_fraction_full 0.975
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            1498
_diffrn_reflns_point_group_measured_fraction_full 0.975
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_theta_full        24.996
_diffrn_reflns_theta_max         24.996
_diffrn_reflns_theta_min         2.621
_diffrn_ambient_temperature      298(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.975
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1431
_reflns_number_total             1498
_reflns_special_details          
;
 _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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_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    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.336
_refine_diff_density_min         -0.393
_refine_diff_density_rms         0.086
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.161
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     146
_refine_ls_number_reflns         1498
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0573
_refine_ls_R_factor_gt           0.0544
_refine_ls_restrained_S_all      1.161
_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)+(0.0292P)²+1.9301P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1338
_refine_ls_wR_factor_ref         0.1355
_refine_special_details          
;
 Refined as a 2-component twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.633(5)
 0.367(5)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups, All N(H,H) groups, All N(H,H,H) groups
3.a Riding coordinates:
 N3(H3), N5(H5A,H5B,H5C), N4(H4), N1(H1A,H1B), N2(H2A)
3.b Aromatic/amide H refined with riding coordinates:
 C2(H2)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_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 0.2244(4) -0.0074(3) 0.89730(16) 0.0236(6) Uani 1 1 d . . . A 1
O3 O 0.0863(4) -0.1181(2) 0.77402(16) 0.0193(6) Uani 1 1 d . . . B 2
O2 O 0.0746(4) 0.1138(3) 0.78290(17) 0.0263(6) Uani 1 1 d . . . C 1
N6 N 0.1300(4) -0.0024(3) 0.81897(19) 0.0155(6) Uani 1 1 d . . . . .
O4 O 0.4230(4) 0.0504(3) 0.23053(16) 0.0209(6) Uani 1 1 d . . . . .
N7 N 0.3884(4) 0.1387(3) 0.16299(19) 0.0175(6) Uani 1 1 d . . . . .
O6 O 0.2928(4) 0.0970(3) 0.08878(17) 0.0274(7) Uani 1 1 d . . . D 2
O5 O 0.4502(4) 0.2636(3) 0.17023(17) 0.0262(6) Uani 1 1 d . . . . .
N3 N 0.8567(4) 0.1731(3) 0.57857(19) 0.0166(6) Uani 1 1 d . . . . .
H3 H 0.858163 0.242075 0.618038 0.020 Uiso 1 1 d R . . . .
N5 N 0.6477(4) 0.2810(3) 0.34876(18) 0.0161(6) Uani 1 1 d . . . . .
H5A H 0.684581 0.220850 0.307921 0.019 Uiso 1 1 d R . . . .
H5B H 0.636251 0.364440 0.324821 0.019 Uiso 1 1 d R . . . .
H5C H 0.536871 0.242470 0.361591 0.019 Uiso 1 1 d R . . . .
N4 N 0.7730(4) 0.2914(3) 0.43392(19) 0.0159(6) Uani 1 1 d . . . . .
H4 H 0.757203 0.372630 0.459750 0.019 Uiso 1 1 d R . . . .
N1 N 0.7362(4) -0.1918(3) 0.5663(2) 0.0173(6) Uani 1 1 d . . . . .
H1A H 0.808833 -0.226211 0.612471 0.021 Uiso 1 1 d R . . . .
H1B H 0.723693 -0.251721 0.520801 0.021 Uiso 1 1 d R . . . .
C2 C 0.7228(5) 0.0293(3) 0.4660(2) 0.0134(7) Uani 1 1 d . . . . .
H2 H 0.667563 -0.005043 0.406513 0.016 Uiso 1 1 calc R . . . .
N2 N 0.8406(4) 0.0385(3) 0.61593(19) 0.0153(6) Uani 1 1 d . . . . .
H2A H 0.888443 0.024667 0.672502 0.018 Uiso 1 1 d R . . . .
C3 C 0.7764(5) 0.1692(3) 0.4892(2) 0.0132(7) Uani 1 1 d . . . . .
C1 C 0.7671(5) -0.0503(3) 0.5484(2) 0.0133(7) 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 N6 1.237(3) . ?
O3 N6 1.276(4) . ?
O2 N6 1.244(4) . ?
O4 N7 1.268(4) . ?
N7 O6 1.253(4) . ?
N7 O5 1.238(4) . ?
N3 H3 0.8500 . ?
N3 N2 1.368(4) . ?
N3 C3 1.339(4) . ?
N5 H5A 0.8499 . ?
N5 H5B 0.8499 . ?
N5 H5C 0.8500 . ?
N5 N4 1.423(4) . ?
N4 H4 0.8498 . ?
N4 C3 1.380(4) . ?
N1 H1A 0.8500 . ?
N1 H1B 0.8500 . ?
N1 C1 1.363(4) . ?
C2 H2 0.9500 . ?
C2 C3 1.387(4) . ?
C2 C1 1.394(4) . ?
N2 H2A 0.8500 . ?
N2 C1 1.332(4) . ?

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 N6 O2 121.3(3) . . ?
O6 N7 O4 118.9(3) . . ?
O5 N7 O4 120.3(3) . . ?
O5 N7 O6 120.8(3) . . ?
N2 N3 H3 116.2 . . ?
C3 N3 H3 128.6 . . ?
C3 N3 N2 107.5(3) . . ?
H5A N5 H5B 111.0 . . ?
H5A N5 H5C 98.9 . . ?
H5B N5 H5C 114.4 . . ?
N4 N5 H5A 115.8 . . ?
N4 N5 H5B 107.8 . . ?
N4 N5 H5C 108.9 . . ?
N5 N4 H4 109.9 . . ?
C3 N4 N5 114.1(2) . . ?
C3 N4 H4 119.6 . . ?
H1A N1 H1B 110.8 . . ?
C1 N1 H1A 115.0 . . ?
C1 N1 H1B 120.4 . . ?
C3 C2 H2 127.3 . . ?
C3 C2 C1 105.4(3) . . ?
C1 C2 H2 127.3 . . ?
N3 N2 H2A 117.8 . . ?
C1 N2 N3 109.3(3) . . ?
C1 N2 H2A 132.5 . . ?
N3 C3 N4 120.0(3) . . ?
N3 C3 C2 109.3(3) . . ?
N4 C3 C2 130.5(3) . . ?
N1 C1 C2 130.0(3) . . ?
N2 C1 N1 121.6(3) . . ?
N2 C1 C2 108.3(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N3 N2 C1 N1 179.8(3) . . . . ?
N3 N2 C1 C2 -3.5(4) . . . . ?
N5 N4 C3 N3 -167.5(3) . . . . ?
N5 N4 C3 C2 18.8(5) . . . . ?
N2 N3 C3 N4 -179.8(3) . . . . ?
N2 N3 C3 C2 -4.8(4) . . . . ?
C3 N3 N2 C1 5.1(4) . . . . ?
C3 C2 C1 N1 176.9(3) . . . . ?
C3 C2 C1 N2 0.5(4) . . . . ?
C1 C2 C3 N3 2.7(4) . . . . ?
C1 C2 C3 N4 177.0(3) . . . . ?


_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.633(5)
2 0.367(5)

####################################################################### 
# 
# 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_a
_database_code_depnum_ccdc_archive 'CCDC 2005508'
_audit_update_record             
;
2020-05-24 deposited with the CCDC.	2021-04-28 downloaded from the CCDC.
;
_audit_creation_date             2019-01-08
_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(C H N6 O2), C3 H9 N5, 2(H2 O)'
_chemical_formula_sum            'C5 H15 N17 O6'
_chemical_formula_weight         409.34
_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      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   9.5665(19)
_cell_length_b                   6.7226(13)
_cell_length_c                   50.601(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3254.2(11)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    6871
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      27.4160
_cell_measurement_theta_min      1.6098
_shelx_estimated_absorpt_T_max   0.986
_shelx_estimated_absorpt_T_min   0.978
_exptl_absorpt_coefficient_mu    0.146
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.6882
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2008)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.671
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1696
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0736
_diffrn_reflns_av_unetI/netI     0.0778
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.963
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       63
_diffrn_reflns_limit_l_min       -48
_diffrn_reflns_number            11169
_diffrn_reflns_point_group_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.963
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.358
_diffrn_reflns_theta_min         0.805
_diffrn_ambient_temperature      298(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.963
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2994
_reflns_number_total             3556
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_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    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.318
_refine_diff_density_min         -0.300
_refine_diff_density_rms         0.079
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.212
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     261
_refine_ls_number_reflns         3556
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1103
_refine_ls_R_factor_gt           0.0924
_refine_ls_restrained_S_all      1.212
_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)+(0.0340P)²+7.5788P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1753
_refine_ls_wR_factor_ref         0.1848
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups, All N(H,H) groups, All N(H,H,H) groups,
  All O(H,H) groups
2.a Riding coordinates:
 N2(H2), N10(H10), N11(H11A,H11B), N13(H13), N15(H15A,H15B,H15C), O5(H5A,H5B),
 O6(H6A,H6B)
2.b Aromatic/amide H refined with riding coordinates:
 C4(H4)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_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 0.4329(3) 0.9688(4) 0.59084(5) 0.0287(6) Uani 1 1 d . . . . .
O2 O 0.4999(3) 0.8707(4) 0.55113(5) 0.0317(7) Uani 1 1 d . . . . .
N1 N 0.2689(3) 0.9025(5) 0.56171(6) 0.0244(7) Uani 1 1 d . . . . .
N2 N 0.3112(3) 0.7909(5) 0.51489(5) 0.0219(6) Uani 1 1 d . . . . .
H2 H 0.399482 0.790981 0.513053 0.026 Uiso 1 1 d R . . . .
N3 N 0.2228(3) 0.7446(5) 0.49467(6) 0.0262(7) Uani 1 1 d . . . . .
N4 N 0.0966(3) 0.7665(5) 0.50415(6) 0.0262(7) Uani 1 1 d . . . . .
N5 N 0.0974(3) 0.8263(5) 0.52974(6) 0.0244(7) Uani 1 1 d . . . . .
N16 N 0.4025(3) 0.9120(5) 0.56691(6) 0.0244(7) Uani 1 1 d . . . . .
C1 C 0.2336(4) 0.8402(5) 0.53625(7) 0.0221(7) Uani 1 1 d . . . . .
O3 O 0.0355(3) 0.3876(4) 0.33764(5) 0.0292(6) Uani 1 1 d . . . . .
O4 O -0.0042(3) 0.4826(4) 0.29663(5) 0.0290(6) Uani 1 1 d . . . . .
N6 N 0.2168(3) 0.4663(5) 0.31282(6) 0.0243(7) Uani 1 1 d . . . . .
N7 N 0.4065(3) 0.5271(5) 0.28495(6) 0.0255(7) Uani 1 1 d . . . . .
N8 N 0.4271(3) 0.5763(5) 0.25914(6) 0.0261(7) Uani 1 1 d . . . . .
N9 N 0.3083(3) 0.5967(5) 0.24667(6) 0.0265(7) Uani 1 1 d . . . . .
N10 N 0.2061(3) 0.5620(5) 0.26470(6) 0.0235(7) Uani 1 1 d . . . . .
H10 H 0.121435 0.576140 0.259983 0.028 Uiso 1 1 d R . . . .
N11 N 0.3317(3) 0.6163(5) 0.43907(6) 0.0302(8) Uani 1 1 d . . . . .
H11A H 0.252876 0.629873 0.447054 0.036 Uiso 1 1 d R . . . .
H11B H 0.408456 0.638683 0.447414 0.036 Uiso 1 1 d R . . . .
N12 N 0.2159(3) 0.5238(5) 0.39987(6) 0.0239(7) Uani 1 1 d . . . . .
N13 N 0.2521(3) 0.4686(5) 0.37433(5) 0.0235(7) Uani 1 1 d . . . . .
H13 H 0.188445 0.440922 0.363214 0.028 Uiso 1 1 d R . . . .
N14 N 0.4551(3) 0.4031(5) 0.34918(6) 0.0241(7) Uani 1 1 d . . . . .
N15 N 0.5903(3) 0.4878(5) 0.34404(6) 0.0235(7) Uani 1 1 d . . . . .
H15A H 0.617472 0.455444 0.328655 0.028 Uiso 1 1 d R . . . .
H15B H 0.594742 0.613674 0.342705 0.028 Uiso 1 1 d R . . . .
H15C H 0.652312 0.450154 0.355025 0.028 Uiso 1 1 d R . . . .
N17 N 0.0798(3) 0.4475(5) 0.31508(6) 0.0240(7) Uani 1 1 d . . . . .
C2 C 0.2671(4) 0.5192(5) 0.28823(7) 0.0226(7) Uani 1 1 d . . . . .
C3 C 0.3348(4) 0.5591(5) 0.41365(7) 0.0221(7) Uani 1 1 d . . . . .
C4 C 0.4496(4) 0.5251(6) 0.39674(7) 0.0243(8) Uani 1 1 d . . . . .
H4 H 0.545935 0.538818 0.400958 0.029 Uiso 1 1 calc R . . . .
C5 C 0.3930(4) 0.4677(5) 0.37269(7) 0.0205(7) Uani 1 1 d . . . . .
O5 O 0.7531(3) 0.2835(4) 0.37928(5) 0.0287(6) Uani 1 1 d . . . . .
H5A H 0.808404 0.345302 0.389214 0.034 Uiso 1 1 d R . . . .
H5B H 0.707294 0.226462 0.391264 0.034 Uiso 1 1 d R . . . .
O6 O 0.7419(3) 0.2764(4) 0.30787(5) 0.0280(6) Uani 1 1 d . . . . .
H6A H 0.711188 0.226408 0.293797 0.034 Uiso 1 1 d R . . . .
H6B H 0.820328 0.315708 0.302547 0.034 Uiso 1 1 d R . . . .
H12 H 0.125(4) 0.523(5) 0.4037(6) 0.009(8) Uiso 1 1 d . . . . .
H14 H 0.389(5) 0.409(7) 0.3341(9) 0.045(14) 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
O1 N16 1.303(4) . ?
O2 N16 1.258(4) . ?
N1 N16 1.307(4) . ?
N1 C1 1.396(4) . ?
N2 H2 0.8499 . ?
N2 N3 1.364(4) . ?
N2 C1 1.352(4) . ?
N3 N4 1.307(4) . ?
N4 N5 1.356(4) . ?
N5 C1 1.348(5) . ?
O3 N17 1.283(4) . ?
O4 N17 1.254(4) . ?
N6 N17 1.321(4) . ?
N6 C2 1.381(5) . ?
N7 N8 1.362(4) . ?
N7 C2 1.345(5) . ?
N8 N9 1.308(4) . ?
N9 N10 1.357(4) . ?
N10 H10 0.8499 . ?
N10 C2 1.356(4) . ?
N11 H11A 0.8602 . ?
N11 H11B 0.8602 . ?
N11 C3 1.343(5) . ?
N12 N13 1.388(4) . ?
N12 C3 1.356(5) . ?
N12 H12 0.89(4) . ?
N13 H13 0.8500 . ?
N13 C5 1.350(5) . ?
N14 N15 1.437(4) . ?
N14 C5 1.399(4) . ?
N14 H14 0.99(5) . ?
N15 H15A 0.8492 . ?
N15 H15B 0.8499 . ?
N15 H15C 0.8510 . ?
C3 C4 1.411(5) . ?
C4 H4 0.9500 . ?
C4 C5 1.387(5) . ?
O5 H5A 0.8400 . ?
O5 H5B 0.8403 . ?
O6 H6A 0.8401 . ?
O6 H6B 0.8400 . ?

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
N16 N1 C1 115.9(3) . . ?
N3 N2 H2 122.3 . . ?
C1 N2 H2 129.3 . . ?
C1 N2 N3 108.4(3) . . ?
N4 N3 N2 105.8(3) . . ?
N3 N4 N5 112.3(3) . . ?
C1 N5 N4 105.0(3) . . ?
O1 N16 N1 114.8(3) . . ?
O2 N16 O1 119.3(3) . . ?
O2 N16 N1 125.9(3) . . ?
N2 C1 N1 132.8(3) . . ?
N5 C1 N1 118.7(3) . . ?
N5 C1 N2 108.6(3) . . ?
N17 N6 C2 116.6(3) . . ?
C2 N7 N8 105.8(3) . . ?
N9 N8 N7 111.2(3) . . ?
N8 N9 N10 106.5(3) . . ?
N9 N10 H10 118.6 . . ?
C2 N10 N9 108.5(3) . . ?
C2 N10 H10 132.9 . . ?
H11A N11 H11B 120.0 . . ?
C3 N11 H11A 120.0 . . ?
C3 N11 H11B 120.1 . . ?
N13 N12 H12 116(2) . . ?
C3 N12 N13 108.4(3) . . ?
C3 N12 H12 135(2) . . ?
N12 N13 H13 119.7 . . ?
C5 N13 N12 107.9(3) . . ?
C5 N13 H13 132.4 . . ?
N15 N14 H14 115(3) . . ?
C5 N14 N15 114.4(3) . . ?
C5 N14 H14 112(3) . . ?
N14 N15 H15A 109.8 . . ?
N14 N15 H15B 117.0 . . ?
N14 N15 H15C 113.0 . . ?
H15A N15 H15B 99.6 . . ?
H15A N15 H15C 108.0 . . ?
H15B N15 H15C 108.3 . . ?
O3 N17 N6 115.8(3) . . ?
O4 N17 O3 120.6(3) . . ?
O4 N17 N6 123.6(3) . . ?
N7 C2 N6 117.8(3) . . ?
N7 C2 N10 108.0(3) . . ?
N10 C2 N6 134.1(3) . . ?
N11 C3 N12 121.6(3) . . ?
N11 C3 C4 130.1(3) . . ?
N12 C3 C4 108.3(3) . . ?
C3 C4 H4 127.1 . . ?
C5 C4 C3 105.8(3) . . ?
C5 C4 H4 127.1 . . ?
N13 C5 N14 118.5(3) . . ?
N13 C5 C4 109.6(3) . . ?
C4 C5 N14 131.8(3) . . ?
H5A O5 H5B 97.0 . . ?
H6A O6 H6B 99.6 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N2 N3 N4 N5 0.3(4) . . . . ?
N3 N2 C1 N1 -178.6(4) . . . . ?
N3 N2 C1 N5 -0.2(4) . . . . ?
N3 N4 N5 C1 -0.4(4) . . . . ?
N4 N5 C1 N1 179.1(3) . . . . ?
N4 N5 C1 N2 0.4(4) . . . . ?
N16 N1 C1 N2 -2.1(6) . . . . ?
N16 N1 C1 N5 179.6(3) . . . . ?
C1 N1 N16 O1 -179.4(3) . . . . ?
C1 N1 N16 O2 0.1(6) . . . . ?
C1 N2 N3 N4 -0.1(4) . . . . ?
N7 N8 N9 N10 0.5(4) . . . . ?
N8 N7 C2 N6 178.2(3) . . . . ?
N8 N7 C2 N10 0.3(4) . . . . ?
N8 N9 N10 C2 -0.3(4) . . . . ?
N9 N10 C2 N6 -177.4(4) . . . . ?
N9 N10 C2 N7 0.0(4) . . . . ?
N11 C3 C4 C5 179.7(4) . . . . ?
N12 N13 C5 N14 175.7(3) . . . . ?
N12 N13 C5 C4 -1.0(4) . . . . ?
N12 C3 C4 C5 -0.4(4) . . . . ?
N13 N12 C3 N11 179.7(3) . . . . ?
N13 N12 C3 C4 -0.3(4) . . . . ?
N15 N14 C5 N13 152.6(3) . . . . ?
N15 N14 C5 C4 -31.5(6) . . . . ?
N17 N6 C2 N7 -175.9(3) . . . . ?
N17 N6 C2 N10 1.3(6) . . . . ?
C2 N6 N17 O3 176.3(3) . . . . ?
C2 N6 N17 O4 -2.9(5) . . . . ?
C2 N7 N8 N9 -0.5(4) . . . . ?
C3 N12 N13 C5 0.8(4) . . . . ?
C3 C4 C5 N13 0.9(4) . . . . ?
C3 C4 C5 N14 -175.3(4) . . . . ?


_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_bwn18435
_database_code_depnum_ccdc_archive 'CCDC 2005507'
_audit_update_record             
;
2020-05-24 deposited with the CCDC.	2021-04-28 downloaded from the CCDC.
;
_audit_creation_date             2018-12-10
_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(C6 H2 N3 O8), 5(H2 O), C3 H9 N5'
_chemical_formula_sum            'C15 H23 N11 O21'
_chemical_formula_weight         693.44
_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                   9.4079(19)
_cell_length_b                   10.355(2)
_cell_length_c                   13.922(3)
_cell_angle_alpha                100.85(3)
_cell_angle_beta                 90.26(3)
_cell_angle_gamma                92.14(3)
_cell_volume                     1331.0(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    ?
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      ?
_cell_measurement_theta_min      ?
_shelx_estimated_absorpt_T_max   0.984
_shelx_estimated_absorpt_T_min   0.967
_exptl_absorpt_coefficient_mu    0.163
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.730
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       ?
_exptl_crystal_F_000             716
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0367
_diffrn_reflns_av_unetI/netI     0.0383
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            14862
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.502
_diffrn_reflns_theta_min         2.615
_diffrn_ambient_temperature      298(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5477
_reflns_number_total             6075
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_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         0.402
_refine_diff_density_min         -0.420
_refine_diff_density_rms         0.057
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     456
_refine_ls_number_reflns         6075
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0599
_refine_ls_R_factor_gt           0.0530
_refine_ls_restrained_S_all      1.096
_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)+(0.0469P)²+1.0047P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1205
_refine_ls_wR_factor_ref         0.1257
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, {H20A,H20B} of O20, All N(H) groups, All N(H,H,H) groups
 At 1.5 times of:
  All O(H) groups, {H19A,H19B} of O19, {H17A,H17B} of O17, {H21A,H21B} of O21
2.a Riding coordinates:
 O20(H20A,H20B)
2.b Free rotating group:
 O17(H17A,H17B), O19(H19A,H19B), O21(H21A,H21B)
2.c Aromatic/amide H refined with riding coordinates:
 C7(H7), N3(H3A), N4(H4), C2(H2A), C11(H11)
2.d Idealised Me refined as rotating group:
 N1(H1A,H1B,H1C)
2.e Idealised tetrahedral OH refined as rotating group:
 O3(H3), O13(H13)
;
_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
O1 O 0.74079(16) 0.02172(14) 0.25345(11) 0.0275(3) Uani 1 1 d . . . . .
O2 O 0.62988(17) -0.09865(14) 0.34256(11) 0.0295(3) Uani 1 1 d . . . . .
O3 O 0.67439(16) 0.09151(14) 0.51316(10) 0.0246(3) Uani 1 1 d . . . . .
H3 H 0.675218 0.126121 0.572801 0.037 Uiso 1 1 calc GR . . . .
O4 O 0.61278(16) 0.27047(14) 0.66088(10) 0.0255(3) Uani 1 1 d . . . . .
O5 O 0.44720(17) 0.40717(15) 0.64974(10) 0.0282(3) Uani 1 1 d . . . . .
O6 O 0.25253(17) 0.45212(16) 0.35152(11) 0.0327(4) Uani 1 1 d . . . . .
O7 O 0.3260(2) 0.3506(2) 0.21466(11) 0.0579(6) Uani 1 1 d . . . . .
O8 O 0.48723(14) 0.14261(13) 0.20946(9) 0.0200(3) Uani 1 1 d . . . . .
N6 N 0.65482(18) 0.00645(16) 0.31684(11) 0.0201(3) Uani 1 1 d . . . . .
N7 N 0.52327(18) 0.31793(16) 0.61175(11) 0.0209(3) Uani 1 1 d . . . . .
N8 N 0.32681(18) 0.36932(17) 0.30352(12) 0.0228(4) Uani 1 1 d . . . . .
C4 C 0.5768(2) 0.12072(18) 0.36381(13) 0.0179(4) Uani 1 1 d . . . . .
C5 C 0.5899(2) 0.15790(18) 0.46420(13) 0.0188(4) Uani 1 1 d . . . . .
C6 C 0.5121(2) 0.26797(19) 0.50922(13) 0.0189(4) Uani 1 1 d . . . . .
C7 C 0.4259(2) 0.33169(19) 0.45377(13) 0.0191(4) Uani 1 1 d . . . . .
H7 H 0.372243 0.403204 0.485173 0.023 Uiso 1 1 calc R . . . .
C8 C 0.4169(2) 0.29288(19) 0.35393(13) 0.0188(4) Uani 1 1 d . . . . .
C9 C 0.49349(19) 0.18352(18) 0.30051(13) 0.0169(4) Uani 1 1 d . . . . .
O9 O 0.15351(17) -0.00711(15) 0.15465(10) 0.0299(3) Uani 1 1 d . . . . .
O10 O 0.25082(17) -0.04255(15) 0.28709(11) 0.0302(3) Uani 1 1 d . . . . .
O11 O 0.07328(18) 0.13394(16) 0.59487(11) 0.0344(4) Uani 1 1 d . . . . .
O12 O -0.07442(17) 0.29209(16) 0.61578(11) 0.0326(4) Uani 1 1 d . . . . .
O13 O -0.15290(16) 0.40130(15) 0.47282(10) 0.0280(3) Uani 1 1 d . . . . .
H13 H -0.148413 0.395901 0.532205 0.042 Uiso 1 1 calc GR . . . .
O14 O -0.1045(2) 0.49684(19) 0.2769(2) 0.0745(8) Uani 1 1 d . . . . .
O15 O -0.27347(17) 0.35281(16) 0.24347(13) 0.0347(4) Uani 1 1 d . . . . .
O16 O -0.00759(15) 0.20151(13) 0.16212(10) 0.0223(3) Uani 1 1 d . . . . .
O17 O 0.09939(16) 0.40031(14) 0.07513(10) 0.0239(3) Uani 1 1 d . . . . .
H17A H 0.118124 0.472068 0.114737 0.036 Uiso 1 1 d G . . . .
H17B H 0.082226 0.344461 0.111613 0.036 Uiso 1 1 d G . . . .
O18 O 0.17012(18) 0.64506(16) 0.17491(11) 0.0294(3) Uani 1 1 d . . . . .
O19 O -0.08022(17) 0.77271(15) 0.18310(11) 0.0304(3) Uani 1 1 d . . . . .
H19A H -0.091449 0.824764 0.237298 0.046 Uiso 1 1 d G . . . .
H19B H -0.143970 0.711206 0.176203 0.046 Uiso 1 1 d G . . . .
O20 O 0.19249(16) 0.64547(14) -0.02368(10) 0.0256(3) Uani 1 1 d . . . . .
H20A H 0.106762 0.625334 -0.038362 0.031 Uiso 1 1 d R . . . .
H20B H 0.198592 0.661074 0.037668 0.031 Uiso 1 1 d R . . . .
O21 O 0.86419(17) -0.09772(15) 0.02376(11) 0.0298(3) Uani 1 1 d . . . . .
H21A H 0.903701 -0.132921 0.066930 0.045 Uiso 1 1 d G . . . .
H21B H 0.912768 -0.111013 -0.028237 0.045 Uiso 1 1 d G . . . .
N1 N 0.70419(17) 0.11257(16) 0.06778(11) 0.0199(3) Uani 1 1 d . . . . .
H1A H 0.766472 0.046938 0.065511 0.024 Uiso 1 1 calc GR . . . .
H1B H 0.644060 0.112091 0.118731 0.024 Uiso 1 1 calc GR . . . .
H1C H 0.753099 0.191447 0.075983 0.024 Uiso 1 1 calc GR . . . .
N2 N 0.62332(17) 0.09236(16) -0.02234(12) 0.0198(3) Uani 1 1 d . . . . .
N3 N 0.44985(17) 0.24502(16) 0.04199(11) 0.0195(3) Uani 1 1 d . . . . .
H3A H 0.446787 0.225067 0.100679 0.023 Uiso 1 1 calc R . . . .
N4 N 0.37130(18) 0.33791(16) 0.00981(12) 0.0213(3) Uani 1 1 d . . . . .
H4 H 0.311944 0.390471 0.045137 0.026 Uiso 1 1 calc R . . . .
N5 N 0.3292(2) 0.4099(2) -0.13809(14) 0.0283(4) Uani 1 1 d . . . . .
N9 N 0.16765(17) 0.01658(16) 0.24432(11) 0.0195(3) Uani 1 1 d . . . . .
N10 N 0.00320(19) 0.21445(17) 0.56267(12) 0.0245(4) Uani 1 1 d . . . . .
N11 N -0.15703(18) 0.38947(16) 0.27803(12) 0.0229(4) Uani 1 1 d . . . . .
C1 C 0.5316(2) 0.19038(18) -0.03137(13) 0.0181(4) Uani 1 1 d . . . . .
C2 C 0.5037(2) 0.24286(19) -0.11369(14) 0.0208(4) Uani 1 1 d . . . . .
H2A H 0.545859 0.220808 -0.176215 0.025 Uiso 1 1 calc R . . . .
C3 C 0.4007(2) 0.33469(19) -0.08508(14) 0.0203(4) Uani 1 1 d . . . . .
C10 C 0.0838(2) 0.11793(18) 0.30044(13) 0.0187(4) Uani 1 1 d . . . . .
C11 C 0.0857(2) 0.12657(19) 0.40032(14) 0.0197(4) Uani 1 1 d . . . . .
H11 H 0.142235 0.068856 0.428392 0.024 Uiso 1 1 calc R . . . .
C12 C 0.0066(2) 0.21794(19) 0.46030(13) 0.0207(4) Uani 1 1 d . . . . .
C13 C -0.0752(2) 0.30800(19) 0.42046(14) 0.0203(4) Uani 1 1 d . . . . .
C14 C -0.0737(2) 0.29688(18) 0.32079(14) 0.0197(4) Uani 1 1 d . . . . .
C15 C 0.0012(2) 0.20249(18) 0.25226(13) 0.0186(4) Uani 1 1 d . . . . .
H5A H 0.293(3) 0.484(3) -0.102(2) 0.036(7) Uiso 1 1 d . . . . .
H5B H 0.368(3) 0.417(3) -0.191(2) 0.040(8) Uiso 1 1 d . . . . .
H18A H 0.084(4) 0.692(3) 0.189(2) 0.053(9) Uiso 1 1 d . . . . .
H18B H 0.220(4) 0.651(4) 0.231(3) 0.081(12) Uiso 1 1 d . . . . .
H2 H 0.685(3) 0.080(2) -0.0710(18) 0.026(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
O1 N6 1.228(2) . ?
O2 N6 1.223(2) . ?
O3 H3 0.8400 . ?
O3 C5 1.335(2) . ?
O4 N7 1.253(2) . ?
O5 N7 1.231(2) . ?
O6 N8 1.226(2) . ?
O7 N8 1.216(2) . ?
O8 C9 1.259(2) . ?
N6 C4 1.464(2) . ?
N7 C6 1.426(2) . ?
N8 C8 1.446(2) . ?
C4 C5 1.382(3) . ?
C4 C9 1.436(3) . ?
C5 C6 1.423(3) . ?
C6 C7 1.384(3) . ?
C7 H7 0.9500 . ?
C7 C8 1.374(3) . ?
C8 C9 1.450(3) . ?
O9 N9 1.232(2) . ?
O10 N9 1.229(2) . ?
O11 N10 1.229(2) . ?
O12 N10 1.246(2) . ?
O13 H13 0.8400 . ?
O13 C13 1.339(2) . ?
O14 N11 1.202(2) . ?
O15 N11 1.213(2) . ?
O16 C15 1.255(2) . ?
O17 H17A 0.8499 . ?
O17 H17B 0.8501 . ?
O18 H18A 0.96(3) . ?
O18 H18B 0.90(4) . ?
O19 H19A 0.8503 . ?
O19 H19B 0.8499 . ?
O20 H20A 0.8400 . ?
O20 H20B 0.8402 . ?
O21 H21A 0.8502 . ?
O21 H21B 0.8498 . ?
N1 H1A 0.9100 . ?
N1 H1B 0.9100 . ?
N1 H1C 0.9100 . ?
N1 N2 1.441(2) . ?
N2 C1 1.379(2) . ?
N2 H2 0.89(3) . ?
N3 H3A 0.8800 . ?
N3 N4 1.373(2) . ?
N3 C1 1.333(2) . ?
N4 H4 0.8800 . ?
N4 C3 1.346(2) . ?
N5 C3 1.362(3) . ?
N5 H5A 0.91(3) . ?
N5 H5B 0.83(3) . ?
N9 C10 1.447(2) . ?
N10 C12 1.433(2) . ?
N11 C14 1.468(2) . ?
C1 C2 1.386(3) . ?
C2 H2A 0.9500 . ?
C2 C3 1.390(3) . ?
C10 C11 1.377(3) . ?
C10 C15 1.445(3) . ?
C11 H11 0.9500 . ?
C11 C12 1.381(3) . ?
C12 C13 1.419(3) . ?
C13 C14 1.371(3) . ?
C14 C15 1.439(3) . ?

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
C5 O3 H3 109.5 . . ?
O1 N6 C4 117.98(16) . . ?
O2 N6 O1 123.88(17) . . ?
O2 N6 C4 118.14(16) . . ?
O4 N7 C6 118.60(16) . . ?
O5 N7 O4 121.55(16) . . ?
O5 N7 C6 119.84(17) . . ?
O6 N8 C8 119.15(16) . . ?
O7 N8 O6 121.21(18) . . ?
O7 N8 C8 119.64(16) . . ?
C5 C4 N6 117.37(16) . . ?
C5 C4 C9 126.18(17) . . ?
C9 C4 N6 116.45(15) . . ?
O3 C5 C4 119.33(17) . . ?
O3 C5 C6 123.77(17) . . ?
C4 C5 C6 116.89(17) . . ?
C5 C6 N7 121.32(17) . . ?
C7 C6 N7 118.08(17) . . ?
C7 C6 C5 120.58(17) . . ?
C6 C7 H7 119.6 . . ?
C8 C7 C6 120.86(18) . . ?
C8 C7 H7 119.6 . . ?
N8 C8 C9 121.05(16) . . ?
C7 C8 N8 115.89(17) . . ?
C7 C8 C9 123.06(17) . . ?
O8 C9 C4 121.96(17) . . ?
O8 C9 C8 125.62(17) . . ?
C4 C9 C8 112.38(16) . . ?
C13 O13 H13 109.5 . . ?
H17A O17 H17B 104.5 . . ?
H18A O18 H18B 108(3) . . ?
H19A O19 H19B 109.5 . . ?
H20A O20 H20B 107.0 . . ?
H21A O21 H21B 109.5 . . ?
H1A N1 H1B 109.5 . . ?
H1A N1 H1C 109.5 . . ?
H1B N1 H1C 109.5 . . ?
N2 N1 H1A 109.5 . . ?
N2 N1 H1B 109.5 . . ?
N2 N1 H1C 109.5 . . ?
N1 N2 H2 107.4(16) . . ?
C1 N2 N1 115.41(15) . . ?
C1 N2 H2 111.5(16) . . ?
N4 N3 H3A 126.0 . . ?
C1 N3 H3A 126.0 . . ?
C1 N3 N4 107.92(15) . . ?
N3 N4 H4 125.9 . . ?
C3 N4 N3 108.19(15) . . ?
C3 N4 H4 125.9 . . ?
C3 N5 H5A 114.3(17) . . ?
C3 N5 H5B 113.5(19) . . ?
H5A N5 H5B 118(3) . . ?
O9 N9 C10 118.54(16) . . ?
O10 N9 O9 122.11(16) . . ?
O10 N9 C10 119.35(16) . . ?
O11 N10 O12 122.19(17) . . ?
O11 N10 C12 119.62(17) . . ?
O12 N10 C12 118.17(17) . . ?
O14 N11 O15 123.38(19) . . ?
O14 N11 C14 118.12(18) . . ?
O15 N11 C14 118.47(17) . . ?
N2 C1 C2 128.00(17) . . ?
N3 C1 N2 122.16(17) . . ?
N3 C1 C2 109.78(17) . . ?
C1 C2 H2A 127.4 . . ?
C1 C2 C3 105.16(16) . . ?
C3 C2 H2A 127.4 . . ?
N4 C3 N5 120.85(18) . . ?
N4 C3 C2 108.87(17) . . ?
N5 C3 C2 130.22(18) . . ?
C11 C10 N9 116.40(17) . . ?
C11 C10 C15 122.85(17) . . ?
C15 C10 N9 120.73(16) . . ?
C10 C11 H11 119.5 . . ?
C10 C11 C12 120.95(18) . . ?
C12 C11 H11 119.5 . . ?
C11 C12 N10 118.26(18) . . ?
C11 C12 C13 120.62(17) . . ?
C13 C12 N10 121.04(17) . . ?
O13 C13 C12 124.87(17) . . ?
O13 C13 C14 118.42(18) . . ?
C14 C13 C12 116.71(17) . . ?
C13 C14 N11 117.64(17) . . ?
C13 C14 C15 126.70(18) . . ?
C15 C14 N11 115.66(16) . . ?
O16 C15 C10 127.34(17) . . ?
O16 C15 C14 120.53(17) . . ?
C14 C15 C10 112.12(16) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 N6 C4 C5 -121.84(19) . . . . ?
O1 N6 C4 C9 58.2(2) . . . . ?
O2 N6 C4 C5 58.6(2) . . . . ?
O2 N6 C4 C9 -121.32(19) . . . . ?
O3 C5 C6 N7 1.9(3) . . . . ?
O3 C5 C6 C7 -179.68(18) . . . . ?
O4 N7 C6 C5 6.2(3) . . . . ?
O4 N7 C6 C7 -172.18(17) . . . . ?
O5 N7 C6 C5 -174.81(18) . . . . ?
O5 N7 C6 C7 6.8(3) . . . . ?
O6 N8 C8 C7 -8.2(3) . . . . ?
O6 N8 C8 C9 172.59(18) . . . . ?
O7 N8 C8 C7 171.7(2) . . . . ?
O7 N8 C8 C9 -7.5(3) . . . . ?
N6 C4 C5 O3 1.7(3) . . . . ?
N6 C4 C5 C6 -179.20(16) . . . . ?
N6 C4 C9 O8 0.2(3) . . . . ?
N6 C4 C9 C8 178.23(16) . . . . ?
N7 C6 C7 C8 176.36(17) . . . . ?
N8 C8 C9 O8 -2.1(3) . . . . ?
N8 C8 C9 C4 179.94(16) . . . . ?
C4 C5 C6 N7 -177.15(17) . . . . ?
C4 C5 C6 C7 1.2(3) . . . . ?
C5 C4 C9 O8 -179.74(18) . . . . ?
C5 C4 C9 C8 -1.7(3) . . . . ?
C5 C6 C7 C8 -2.1(3) . . . . ?
C6 C7 C8 N8 -178.18(17) . . . . ?
C6 C7 C8 C9 1.0(3) . . . . ?
C7 C8 C9 O8 178.77(18) . . . . ?
C7 C8 C9 C4 0.8(3) . . . . ?
C9 C4 C5 O3 -178.38(17) . . . . ?
C9 C4 C5 C6 0.7(3) . . . . ?
O9 N9 C10 C11 169.87(17) . . . . ?
O9 N9 C10 C15 -8.9(3) . . . . ?
O10 N9 C10 C11 -10.5(3) . . . . ?
O10 N9 C10 C15 170.73(17) . . . . ?
O11 N10 C12 C11 2.2(3) . . . . ?
O11 N10 C12 C13 178.78(18) . . . . ?
O12 N10 C12 C11 -176.09(18) . . . . ?
O12 N10 C12 C13 0.5(3) . . . . ?
O13 C13 C14 N11 0.5(3) . . . . ?
O13 C13 C14 C15 -179.15(18) . . . . ?
O14 N11 C14 C13 82.6(3) . . . . ?
O14 N11 C14 C15 -97.6(3) . . . . ?
O15 N11 C14 C13 -99.2(2) . . . . ?
O15 N11 C14 C15 80.5(2) . . . . ?
N1 N2 C1 N3 -43.2(3) . . . . ?
N1 N2 C1 C2 139.9(2) . . . . ?
N2 C1 C2 C3 178.02(19) . . . . ?
N3 N4 C3 N5 174.90(18) . . . . ?
N3 N4 C3 C2 -2.5(2) . . . . ?
N3 C1 C2 C3 0.8(2) . . . . ?
N4 N3 C1 N2 -179.74(17) . . . . ?
N4 N3 C1 C2 -2.4(2) . . . . ?
N9 C10 C11 C12 -178.46(17) . . . . ?
N9 C10 C15 O16 -1.0(3) . . . . ?
N9 C10 C15 C14 -179.71(16) . . . . ?
N10 C12 C13 O13 4.8(3) . . . . ?
N10 C12 C13 C14 -174.98(18) . . . . ?
N11 C14 C15 O16 -0.6(3) . . . . ?
N11 C14 C15 C10 178.22(16) . . . . ?
C1 N3 N4 C3 3.0(2) . . . . ?
C1 C2 C3 N4 1.0(2) . . . . ?
C1 C2 C3 N5 -176.0(2) . . . . ?
C10 C11 C12 N10 174.62(18) . . . . ?
C10 C11 C12 C13 -2.0(3) . . . . ?
C11 C10 C15 O16 -179.67(19) . . . . ?
C11 C10 C15 C14 1.6(3) . . . . ?
C11 C12 C13 O13 -178.73(18) . . . . ?
C11 C12 C13 C14 1.5(3) . . . . ?
C12 C13 C14 N11 -179.70(17) . . . . ?
C12 C13 C14 C15 0.6(3) . . . . ?
C13 C14 C15 O16 179.08(19) . . . . ?
C13 C14 C15 C10 -2.1(3) . . . . ?
C15 C10 C11 C12 0.3(3) . . . . ?


_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_bwn18400
_database_code_depnum_ccdc_archive 'CCDC 2005506'
_audit_update_record             
;
2020-05-24 deposited with the CCDC.	2021-04-28 downloaded from the CCDC.
;
_audit_creation_date             2018-11-13
_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(C6 H2 N3 O7), H2 O, C3 H9 N5'
_chemical_formula_sum            'C15 H15 N11 O15'
_chemical_formula_weight         589.38
_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                   7.8469(16)
_cell_length_b                   12.050(2)
_cell_length_c                   12.748(3)
_cell_angle_alpha                73.00(3)
_cell_angle_beta                 83.11(3)
_cell_angle_gamma                76.27(3)
_cell_volume                     1118.1(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3335
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      27.4855
_cell_measurement_theta_min      2.6761
_shelx_estimated_absorpt_T_max   0.984
_shelx_estimated_absorpt_T_min   0.980
_exptl_absorpt_coefficient_mu    0.158
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9399
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2008)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.751
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       rod
_exptl_crystal_F_000             604
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0285
_diffrn_reflns_av_unetI/netI     0.0265
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            15502
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.494
_diffrn_reflns_theta_min         1.673
_diffrn_ambient_temperature      298(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4817
_reflns_number_total             5127
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_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    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.461
_refine_diff_density_min         -0.400
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.117
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     370
_refine_ls_number_reflns         5127
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0516
_refine_ls_R_factor_gt           0.0477
_refine_ls_restrained_S_all      1.117
_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)+(0.0446P)²+0.6283P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1104
_refine_ls_wR_factor_ref         0.1131
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups, All N(H,H) groups, All N(H,H,H) groups,
  All O(H,H) groups
2.a Riding coordinates:
 O15(H15A,H15B), N2(H2), N3(H3), N1(H1A,H1B,H1C), N4(H4), N5(H5A,H5B)
2.b Aromatic/amide H refined with riding coordinates:
 C7(H7), C13(H13), C5(H5), C15(H15), C2(H2A)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_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
O7 O 0.18651(15) 0.00024(10) 0.65403(9) 0.0239(3) Uani 1 1 d . . . . .
O10 O 0.06526(16) 0.35591(10) 0.37361(9) 0.0247(3) Uani 1 1 d . . . . .
O5 O 0.04055(17) -0.26496(12) 0.88761(11) 0.0327(3) Uani 1 1 d . . . . .
O3 O 0.2975(2) 0.04632(13) 1.11589(11) 0.0392(3) Uani 1 1 d . . . . .
O11 O 0.15508(18) 0.12047(12) 0.37660(12) 0.0382(3) Uani 1 1 d . . . . .
O6 O 0.20320(19) -0.23811(11) 0.73640(11) 0.0341(3) Uani 1 1 d . . . . .
O4 O 0.17340(19) -0.10463(13) 1.15945(10) 0.0370(3) Uani 1 1 d . . . . .
O1 O 0.28217(18) 0.20949(11) 0.61593(10) 0.0328(3) Uani 1 1 d . . . . .
O12 O 0.42749(16) 0.08838(12) 0.31969(11) 0.0324(3) Uani 1 1 d . . . . .
N8 N 0.13796(18) -0.21019(12) 0.81972(12) 0.0236(3) Uani 1 1 d . . . . .
C7 C 0.1860(2) -0.11442(14) 0.95116(13) 0.0216(3) Uani 1 1 d . . . . .
H7 H 0.153441 -0.178676 1.007278 0.026 Uiso 1 1 calc R . . . .
O9 O -0.1291(2) 0.56987(12) 0.28651(11) 0.0451(4) Uani 1 1 d . . . . .
C11 C 0.1290(2) 0.36664(14) 0.27648(13) 0.0194(3) Uani 1 1 d . . . . .
N9 N -0.0275(2) 0.57955(13) 0.20637(12) 0.0282(3) Uani 1 1 d . . . . .
C9 C 0.2142(2) -0.00995(14) 0.75205(13) 0.0196(3) Uani 1 1 d . . . . .
N10 N 0.28060(19) 0.15312(13) 0.31883(11) 0.0237(3) Uani 1 1 d . . . . .
O2 O 0.4590(2) 0.20859(13) 0.73330(12) 0.0408(4) Uani 1 1 d . . . . .
O13 O 0.5014(2) 0.32089(13) -0.06174(12) 0.0455(4) Uani 1 1 d . . . . .
N7 N 0.23811(19) -0.02750(13) 1.09131(12) 0.0267(3) Uani 1 1 d . . . . .
C13 C 0.3407(2) 0.28343(15) 0.14252(13) 0.0221(3) Uani 1 1 d . . . . .
H13 H 0.424897 0.218639 0.126612 0.026 Uiso 1 1 calc R . . . .
N11 N 0.3969(2) 0.40728(14) -0.04276(12) 0.0292(3) Uani 1 1 d . . . . .
C5 C 0.2910(2) 0.06874(14) 0.89642(13) 0.0218(3) Uani 1 1 d . . . . .
H5 H 0.334521 0.127031 0.915482 0.026 Uiso 1 1 calc R . . . .
N6 N 0.34359(19) 0.17055(12) 0.70739(12) 0.0252(3) Uani 1 1 d . . . . .
C4 C 0.2788(2) 0.07472(14) 0.78801(13) 0.0208(3) Uani 1 1 d . . . . .
O14 O 0.3675(2) 0.50568(13) -0.10983(11) 0.0412(4) Uani 1 1 d . . . . .
C14 C 0.3048(2) 0.39313(15) 0.06452(13) 0.0232(3) Uani 1 1 d . . . . .
C8 C 0.1820(2) -0.10875(14) 0.84255(13) 0.0200(3) Uani 1 1 d . . . . .
C6 C 0.2387(2) -0.02392(15) 0.97723(13) 0.0218(3) Uani 1 1 d . . . . .
C10 C 0.0983(2) 0.47530(14) 0.18897(13) 0.0217(3) Uani 1 1 d . . . . .
C15 C 0.1838(2) 0.48857(15) 0.08641(13) 0.0236(3) Uani 1 1 d . . . . .
H15 H 0.159702 0.562317 0.031599 0.028 Uiso 1 1 calc R . . . .
C12 C 0.2512(2) 0.27161(14) 0.24284(13) 0.0204(3) Uani 1 1 d . . . . .
O8 O -0.0271(3) 0.67482(14) 0.13947(14) 0.0722(7) Uani 1 1 d . . . . .
O15 O 0.33897(17) 0.86901(11) 0.51044(10) 0.0295(3) Uani 1 1 d . . . . .
H15A H 0.378729 0.921551 0.461294 0.035 Uiso 1 1 d R . . . .
H15B H 0.302239 0.900591 0.561844 0.035 Uiso 1 1 d R . . . .
N2 N 0.1134(2) 0.74889(13) 0.37134(11) 0.0266(3) Uani 1 1 d . . . . .
H2 H 0.151086 0.798819 0.316857 0.032 Uiso 1 1 d R . . . .
N3 N 0.19386(19) 0.55703(12) 0.49699(11) 0.0245(3) Uani 1 1 d . . . . .
H3 H 0.129858 0.562418 0.554761 0.029 Uiso 1 1 d R . . . .
N1 N 0.04872(19) 0.80796(12) 0.45529(11) 0.0244(3) Uani 1 1 d . . . . .
H1A H 0.001861 0.763894 0.510345 0.029 Uiso 1 1 d R . . . .
H1B H 0.130401 0.828924 0.478005 0.029 Uiso 1 1 d R . . . .
H1C H -0.026899 0.867104 0.422055 0.029 Uiso 1 1 d R . . . .
N4 N 0.30909(18) 0.45193(12) 0.49492(11) 0.0230(3) Uani 1 1 d . . . . .
H4 H 0.303074 0.389593 0.546774 0.028 Uiso 1 1 d R . . . .
C1 C 0.2149(2) 0.63562(14) 0.40025(13) 0.0204(3) Uani 1 1 d . . . . .
N5 N 0.5091(2) 0.37544(14) 0.36757(13) 0.0330(4) Uani 1 1 d . . . . .
H5A H 0.532422 0.308974 0.415811 0.040 Uiso 1 1 d R . . . .
H5B H 0.566522 0.391104 0.306061 0.040 Uiso 1 1 d R . . . .
C3 C 0.3930(2) 0.46511(14) 0.39529(13) 0.0215(3) Uani 1 1 d . . . . .
C2 C 0.3384(2) 0.58209(14) 0.33337(13) 0.0219(3) Uani 1 1 d . . . . .
H2A H 0.377801 0.617610 0.260516 0.026 Uiso 1 1 calc R . . . .


_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
O7 C9 1.259(2) . ?
O10 C11 1.2602(19) . ?
O5 N8 1.2311(19) . ?
O3 N7 1.225(2) . ?
O11 N10 1.228(2) . ?
O6 N8 1.2247(19) . ?
O4 N7 1.234(2) . ?
O1 N6 1.233(2) . ?
O12 N10 1.2282(18) . ?
N8 C8 1.460(2) . ?
C7 H7 0.9500 . ?
C7 C8 1.370(2) . ?
C7 C6 1.389(2) . ?
O9 N9 1.213(2) . ?
C11 C10 1.441(2) . ?
C11 C12 1.443(2) . ?
N9 C10 1.457(2) . ?
N9 O8 1.214(2) . ?
C9 C4 1.443(2) . ?
C9 C8 1.443(2) . ?
N10 C12 1.456(2) . ?
O2 N6 1.223(2) . ?
O13 N11 1.228(2) . ?
N7 C6 1.442(2) . ?
C13 H13 0.9500 . ?
C13 C14 1.392(2) . ?
C13 C12 1.369(2) . ?
N11 O14 1.231(2) . ?
N11 C14 1.451(2) . ?
C5 H5 0.9500 . ?
C5 C4 1.376(2) . ?
C5 C6 1.386(2) . ?
N6 C4 1.452(2) . ?
C14 C15 1.381(2) . ?
C10 C15 1.379(2) . ?
C15 H15 0.9500 . ?
O15 H15A 0.8400 . ?
O15 H15B 0.8400 . ?
N2 H2 0.8500 . ?
N2 N1 1.4330(19) . ?
N2 C1 1.376(2) . ?
N3 H3 0.8500 . ?
N3 N4 1.3756(19) . ?
N3 C1 1.337(2) . ?
N1 H1A 0.8500 . ?
N1 H1B 0.8500 . ?
N1 H1C 0.8500 . ?
N4 H4 0.8499 . ?
N4 C3 1.343(2) . ?
C1 C2 1.382(2) . ?
N5 H5A 0.8501 . ?
N5 H5B 0.8500 . ?
N5 C3 1.342(2) . ?
C3 C2 1.392(2) . ?
C2 H2A 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
O5 N8 C8 117.60(14) . . ?
O6 N8 O5 123.73(15) . . ?
O6 N8 C8 118.63(14) . . ?
C8 C7 H7 120.8 . . ?
C8 C7 C6 118.37(15) . . ?
C6 C7 H7 120.8 . . ?
O10 C11 C10 124.58(15) . . ?
O10 C11 C12 122.84(15) . . ?
C10 C11 C12 112.47(14) . . ?
O9 N9 C10 119.93(14) . . ?
O9 N9 O8 121.56(16) . . ?
O8 N9 C10 118.51(15) . . ?
O7 C9 C4 124.88(15) . . ?
O7 C9 C8 123.20(15) . . ?
C8 C9 C4 111.92(14) . . ?
O11 N10 O12 122.67(15) . . ?
O11 N10 C12 118.30(14) . . ?
O12 N10 C12 118.97(14) . . ?
O3 N7 O4 123.34(15) . . ?
O3 N7 C6 119.32(15) . . ?
O4 N7 C6 117.33(15) . . ?
C14 C13 H13 121.0 . . ?
C12 C13 H13 121.0 . . ?
C12 C13 C14 118.06(15) . . ?
O13 N11 O14 123.29(15) . . ?
O13 N11 C14 118.45(15) . . ?
O14 N11 C14 118.26(15) . . ?
C4 C5 H5 120.6 . . ?
C4 C5 C6 118.75(15) . . ?
C6 C5 H5 120.6 . . ?
O1 N6 C4 119.21(14) . . ?
O2 N6 O1 122.71(15) . . ?
O2 N6 C4 118.08(15) . . ?
C9 C4 N6 119.78(14) . . ?
C5 C4 C9 124.14(15) . . ?
C5 C4 N6 116.02(15) . . ?
C13 C14 N11 118.98(15) . . ?
C15 C14 C13 121.79(15) . . ?
C15 C14 N11 119.23(15) . . ?
C7 C8 N8 116.14(14) . . ?
C7 C8 C9 124.65(15) . . ?
C9 C8 N8 119.20(14) . . ?
C7 C6 N7 118.66(15) . . ?
C5 C6 C7 121.52(15) . . ?
C5 C6 N7 119.82(15) . . ?
C11 C10 N9 120.23(14) . . ?
C15 C10 C11 123.63(15) . . ?
C15 C10 N9 116.15(15) . . ?
C14 C15 H15 120.5 . . ?
C10 C15 C14 119.08(16) . . ?
C10 C15 H15 120.5 . . ?
C11 C12 N10 118.66(14) . . ?
C13 C12 C11 124.80(15) . . ?
C13 C12 N10 116.52(14) . . ?
H15A O15 H15B 104.5 . . ?
N1 N2 H2 107.4 . . ?
C1 N2 H2 117.2 . . ?
C1 N2 N1 118.90(13) . . ?
N4 N3 H3 119.9 . . ?
C1 N3 H3 132.7 . . ?
C1 N3 N4 107.36(13) . . ?
N2 N1 H1A 111.8 . . ?
N2 N1 H1B 111.5 . . ?
N2 N1 H1C 102.0 . . ?
H1A N1 H1B 107.8 . . ?
H1A N1 H1C 111.5 . . ?
H1B N1 H1C 112.3 . . ?
N3 N4 H4 119.6 . . ?
C3 N4 N3 108.73(13) . . ?
C3 N4 H4 130.4 . . ?
N2 C1 C2 126.63(15) . . ?
N3 C1 N2 123.16(15) . . ?
N3 C1 C2 109.93(14) . . ?
H5A N5 H5B 123.1 . . ?
C3 N5 H5A 118.4 . . ?
C3 N5 H5B 117.8 . . ?
N4 C3 C2 108.44(14) . . ?
N5 C3 N4 122.22(16) . . ?
N5 C3 C2 129.34(16) . . ?
C1 C2 C3 105.44(14) . . ?
C1 C2 H2A 127.3 . . ?
C3 C2 H2A 127.3 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O7 C9 C4 C5 172.92(15) . . . . ?
O7 C9 C4 N6 -10.0(2) . . . . ?
O7 C9 C8 N8 8.5(2) . . . . ?
O7 C9 C8 C7 -170.02(15) . . . . ?
O10 C11 C10 N9 -6.5(3) . . . . ?
O10 C11 C10 C15 172.84(16) . . . . ?
O10 C11 C12 N10 10.3(2) . . . . ?
O10 C11 C12 C13 -171.22(16) . . . . ?
O5 N8 C8 C7 29.9(2) . . . . ?
O5 N8 C8 C9 -148.78(15) . . . . ?
O3 N7 C6 C7 174.19(15) . . . . ?
O3 N7 C6 C5 -5.9(2) . . . . ?
O11 N10 C12 C11 36.8(2) . . . . ?
O11 N10 C12 C13 -141.85(17) . . . . ?
O6 N8 C8 C7 -148.09(15) . . . . ?
O6 N8 C8 C9 33.2(2) . . . . ?
O4 N7 C6 C7 -7.3(2) . . . . ?
O4 N7 C6 C5 172.64(15) . . . . ?
O1 N6 C4 C9 29.4(2) . . . . ?
O1 N6 C4 C5 -153.25(15) . . . . ?
O12 N10 C12 C11 -145.99(16) . . . . ?
O12 N10 C12 C13 35.4(2) . . . . ?
O9 N9 C10 C11 -13.3(3) . . . . ?
O9 N9 C10 C15 167.32(17) . . . . ?
C11 C10 C15 C14 0.6(3) . . . . ?
N9 C10 C15 C14 179.97(15) . . . . ?
O2 N6 C4 C9 -149.91(16) . . . . ?
O2 N6 C4 C5 27.4(2) . . . . ?
O13 N11 C14 C13 1.4(3) . . . . ?
O13 N11 C14 C15 -178.49(17) . . . . ?
C13 C14 C15 C10 1.1(3) . . . . ?
N11 C14 C15 C10 -179.08(15) . . . . ?
C4 C9 C8 N8 -172.17(13) . . . . ?
C4 C9 C8 C7 9.3(2) . . . . ?
C4 C5 C6 C7 4.4(2) . . . . ?
C4 C5 C6 N7 -175.50(14) . . . . ?
O14 N11 C14 C13 -177.97(16) . . . . ?
O14 N11 C14 C15 2.2(3) . . . . ?
C14 C13 C12 C11 -3.8(3) . . . . ?
C14 C13 C12 N10 174.74(14) . . . . ?
C8 C7 C6 N7 178.17(14) . . . . ?
C8 C7 C6 C5 -1.7(2) . . . . ?
C8 C9 C4 C5 -6.4(2) . . . . ?
C8 C9 C4 N6 170.72(13) . . . . ?
C6 C7 C8 N8 175.74(14) . . . . ?
C6 C7 C8 C9 -5.7(2) . . . . ?
C6 C5 C4 C9 0.1(2) . . . . ?
C6 C5 C4 N6 -177.13(14) . . . . ?
C10 C11 C12 N10 -173.46(14) . . . . ?
C10 C11 C12 C13 5.0(2) . . . . ?
C12 C11 C10 N9 177.28(14) . . . . ?
C12 C11 C10 C15 -3.3(2) . . . . ?
C12 C13 C14 N11 -179.39(15) . . . . ?
C12 C13 C14 C15 0.5(3) . . . . ?
O8 N9 C10 C11 166.5(2) . . . . ?
O8 N9 C10 C15 -12.9(3) . . . . ?
N2 C1 C2 C3 -174.22(16) . . . . ?
N3 N4 C3 N5 -177.35(15) . . . . ?
N3 N4 C3 C2 3.04(19) . . . . ?
N3 C1 C2 C3 -0.21(19) . . . . ?
N1 N2 C1 N3 32.4(2) . . . . ?
N1 N2 C1 C2 -154.38(16) . . . . ?
N4 N3 C1 N2 176.30(15) . . . . ?
N4 N3 C1 C2 2.04(19) . . . . ?
N4 C3 C2 C1 -1.75(19) . . . . ?
C1 N3 N4 C3 -3.15(19) . . . . ?
N5 C3 C2 C1 178.67(17) . . . . ?


_olex2_submission_special_instructions 'No special instructions were received'
