# Electronic Supplementary Material (ESI) for Physical Chemistry Chemical Physics.
# This journal is © the Owner Societies 2023

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
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data_2tnp_p03_p
_audit_block_doi                 10.5517/ccdc.csd.cc29gp1j
_database_code_depnum_ccdc_archive 'CCDC 2129267'
loop_
_audit_author_name
_audit_author_address
'Liu X.'
;The University of Edinburgh
United Kingdom
;
_audit_update_record             
;
2021-12-16 deposited with the CCDC.	2023-11-20 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT029_2tnp_p03_p          
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.596 Why?
RESPONSE: high pressure data
;
_vrf_PLAT088_2tnp_p03_p          
;
PROBLEM: Poor Data / Parameter Ratio ....................       4.54 Note
RESPONSE: high pressure data
;
_vrf_PLAT110_2tnp_p03_p          
;
PROBLEM: ADDSYM Detects Potential Lattice Translation ...          ? Check
RESPONSE: the nature with this crystal - if the data quality is not good enough to clear locate H atoms, stuture falls into Pseudo sysmetry C2/c ( DOI: 10.1002/anie.201006000)
;
_vrf_PLAT112_2tnp_p03_p          
;
PROBLEM: ADDSYM Detects New (Pseudo) Symm. Elem         I        100 %Fit
RESPONSE: the nature with this crystal - if the data quality is not good enough to clear locate H atoms, stuture falls into Pseudo sysmetry C2/c ( DOI: 10.1002/anie.201006000)
;
_vrf_PLAT113_2tnp_p03_p          
;
PROBLEM: ADDSYM Suggests Possible Pseudo/New  Space Group       I2/a Check
RESPONSE: the nature with this crystal - if the data quality is not good enough to clear locate H atoms, stuture falls into Pseudo sysmetry C2/c ( DOI: 10.1002/anie.201006000)
;
_vrf_PLAT430_2tnp_p03_p          
;
PROBLEM: Short Inter D...A Contact  O005     ..O005     .       2.84 Ang.
RESPONSE: High pressure data
;
# Added during the CSD deposition process: Thursday 16 December 2021 05:11 PM
# end Validation Reply Form

_audit_creation_date             2021-12-16
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
?
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '6(C3 H N5 O6)'
_chemical_formula_sum            'C18 H6 N30 O36'
_chemical_formula_weight         1218.53
_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                   14.815(2)
_cell_length_b                   8.0553(13)
_cell_length_c                   16.9050(19)
_cell_angle_alpha                90
_cell_angle_beta                 92.113(8)
_cell_angle_gamma                90
_cell_volume                     2016.0(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1840
_cell_measurement_temperature    298.0
_cell_measurement_theta_max      25.19
_cell_measurement_theta_min      2.75
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.195
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6616
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0780 before and 0.0591 after correction.
The Ratio of minimum to maximum transmission is 0.8876.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.007
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1224
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0636
_diffrn_reflns_av_unetI/netI     0.0610
_diffrn_reflns_Laue_measured_fraction_full 0.596
_diffrn_reflns_Laue_measured_fraction_max 0.596
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            10884
_diffrn_reflns_point_group_measured_fraction_full 0.596
_diffrn_reflns_point_group_measured_fraction_max 0.596
_diffrn_reflns_theta_full        23.504
_diffrn_reflns_theta_max         23.504
_diffrn_reflns_theta_min         2.411
_diffrn_ambient_temperature      298.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.596
_diffrn_measured_fraction_theta_max 0.596
_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                1214
_reflns_number_total             1775
_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 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.197
_refine_diff_density_min         -0.218
_refine_diff_density_rms         0.046
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     391
_refine_ls_number_reflns         1775
_refine_ls_number_restraints     306
_refine_ls_R_factor_all          0.0833
_refine_ls_R_factor_gt           0.0488
_refine_ls_restrained_S_all      0.973
_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)+(0.0598P)²+2.9315P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1193
_refine_ls_wR_factor_ref         0.1407
_refine_special_details          ?
_olex2_refinement_description    
;
1. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
;
_atom_sites_solution_hydrogens   difmap
_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
O001 O 0.6830(3) 0.5964(6) 0.6506(2) 0.0475(12) Uani 1 1 d . . . . .
O002 O 0.8312(3) 0.5990(6) 0.3542(2) 0.0505(13) Uani 1 1 d . . . . .
O003 O 0.5229(2) 0.4953(6) 0.8124(2) 0.0430(12) Uani 1 1 d . . . . .
O004 O 0.6622(2) 0.4208(5) 0.8338(2) 0.0424(11) Uani 1 1 d . . . . .
O005 O 0.9257(3) 0.1084(7) 0.5102(2) 0.0557(14) Uani 1 1 d . . . . .
O006 O 0.5635(3) 0.1264(6) 0.4813(2) 0.0503(13) Uani 1 1 d . . . . .
O007 O 0.9795(3) 0.4605(6) 0.1767(2) 0.0486(13) Uani 1 1 d . . . . .
O008 O 0.8364(2) 0.4103(5) 0.1584(2) 0.0520(13) Uani 1 1 d . . . . .
O009 O 0.8284(3) 0.4341(6) 0.5268(2) 0.0591(14) Uani 1 1 d . . . . .
O00A O 1.0329(3) 0.2858(6) 0.4943(2) 0.0518(13) Uani 1 1 d . . . . .
O00B O 0.6903(3) 0.4196(6) 0.4840(2) 0.0529(13) Uani 1 1 d . . . . .
N00C N 0.6870(3) 0.7437(8) 0.6345(3) 0.0326(12) Uani 1 1 d . . . . .
O00D O 0.4571(3) 0.3060(6) 0.4993(2) 0.0517(13) Uani 1 1 d . . . . .
O00E O 0.4440(3) 0.5958(7) 0.6557(3) 0.0619(15) Uani 1 1 d . . . . .
N00F N 0.7608(3) 0.9351(7) 0.4648(3) 0.0250(11) Uani 1 1 d . . . . .
N00G N 0.8442(3) 0.2079(6) 0.3751(2) 0.0278(11) Uani 1 1 d . . . . .
O00H O 1.1218(3) 0.2973(6) 0.3406(2) 0.0590(14) Uani 1 1 d . . . . .
N00I N 0.7275(3) 0.9417(6) 0.5363(3) 0.0269(11) Uani 1 1 d . . . . .
N00J N 0.8321(3) 0.2606(6) 0.3006(2) 0.0266(11) Uani 1 1 d . . . . .
N00K N 0.6401(3) 0.2027(7) 0.6259(3) 0.0275(12) Uani 1 1 d . . . . .
N00L N 0.8144(3) 0.7434(7) 0.3672(3) 0.0324(13) Uani 1 1 d . . . . .
N00M N 0.5921(3) 0.4252(6) 0.7940(2) 0.0281(12) Uani 1 1 d . . . . .
O00N O 0.3722(3) 0.3609(6) 0.6565(2) 0.0610(14) Uani 1 1 d . . . . .
O00O O 1.0703(3) 0.5461(7) 0.3265(3) 0.0631(17) Uani 1 1 d . . . . .
N00P N 1.0614(3) 0.3997(8) 0.3338(3) 0.0371(14) Uani 1 1 d . . . . .
N00Q N 0.6605(3) 0.2522(6) 0.6990(2) 0.0274(12) Uani 1 1 d . . . . .
O00R O 0.8272(3) 0.8594(6) 0.3230(2) 0.0602(14) Uani 1 1 d . . . . .
N00S N 0.4398(3) 0.4458(8) 0.6571(3) 0.0367(13) Uani 1 1 d . . . . .
O00T O 0.6650(3) 0.8559(7) 0.6769(3) 0.0606(14) Uani 1 1 d . . . . .
N00U N 0.9074(3) 0.4067(6) 0.1972(2) 0.0328(13) Uani 1 1 d . . . . .
N00V N 0.7574(3) 0.4964(7) 0.5042(2) 0.0336(12) Uani 1 1 d . . . . .
C00W C 0.7219(3) 0.7859(8) 0.5585(3) 0.0224(13) Uani 1 1 d . . . . .
C00X C 0.7777(3) 0.7783(7) 0.4423(3) 0.0237(13) Uani 1 1 d . . . . .
C00Y C 0.9057(3) 0.3375(7) 0.2746(3) 0.0259(13) Uani 1 1 d . . . . .
N00Z N 0.5249(3) 0.2293(7) 0.5199(3) 0.0360(13) Uani 1 1 d . . . . .
C010 C 0.5605(3) 0.2636(7) 0.5988(3) 0.0259(13) Uani 1 1 d . . . . .
C011 C 0.5911(3) 0.3438(7) 0.7183(3) 0.0233(13) Uani 1 1 d . . . . .
N012 N 0.9650(3) 0.2116(7) 0.4728(3) 0.0333(13) Uani 1 1 d . . . . .
C013 C 0.9281(3) 0.2519(7) 0.3941(3) 0.0237(13) Uani 1 1 d . . . . .
C014 C 0.5253(3) 0.3569(7) 0.6577(3) 0.0239(13) Uani 1 1 d . . . . .
C015 C 0.9702(3) 0.3329(7) 0.3342(3) 0.0254(14) Uani 1 1 d . . . . .
C016 C 0.7525(3) 0.6752(8) 0.5019(3) 0.0225(12) Uani 1 1 d . . . . .
H00J H 0.777(4) 0.259(7) 0.272(3) 0.053(17) Uiso 1 1 d . . . . .
H00K H 0.672(3) 0.130(7) 0.598(3) 0.020(14) Uiso 1 1 d . . . . .
H00F H 0.775(4) 1.029(8) 0.438(3) 0.046(19) 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
O001 N00C 1.219(6) . ?
O002 N00L 1.212(6) . ?
O003 N00M 1.221(5) . ?
O004 N00M 1.217(4) . ?
O005 N012 1.207(6) . ?
O006 N00Z 1.212(6) . ?
O007 N00U 1.216(5) . ?
O008 N00U 1.219(5) . ?
O009 N00V 1.215(5) . ?
O00A N012 1.214(5) . ?
O00B N00V 1.208(5) . ?
N00C O00T 1.206(7) . ?
N00C C00W 1.443(8) . ?
O00D N00Z 1.219(5) . ?
O00E N00S 1.210(6) . ?
N00F N00I 1.323(7) . ?
N00F C00X 1.346(8) . ?
N00F H00F 0.91(6) . ?
N00G N00J 1.334(6) . ?
N00G C013 1.322(6) . ?
O00H N00P 1.219(6) . ?
N00I C00W 1.314(7) . ?
N00J C00Y 1.342(7) . ?
N00J H00J 0.93(5) . ?
N00K N00Q 1.323(6) . ?
N00K C010 1.342(6) . ?
N00K H00K 0.90(5) . ?
N00L O00R 1.215(7) . ?
N00L C00X 1.427(8) . ?
N00M C011 1.438(6) . ?
O00N N00S 1.212(6) . ?
O00O N00P 1.194(6) . ?
N00P C015 1.455(6) . ?
N00Q C011 1.316(6) . ?
N00S C014 1.455(7) . ?
N00U C00Y 1.423(6) . ?
N00V C016 1.443(7) . ?
C00W C016 1.396(8) . ?
C00X C016 1.369(8) . ?
C00Y C015 1.362(6) . ?
N00Z C010 1.443(6) . ?
C010 C014 1.367(7) . ?
C011 C014 1.391(6) . ?
N012 C013 1.456(6) . ?
C013 C015 1.372(7) . ?

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
O001 N00C C00W 116.7(5) . . ?
O00T N00C O001 125.5(7) . . ?
O00T N00C C00W 117.8(7) . . ?
N00I N00F C00X 112.1(5) . . ?
N00I N00F H00F 122(5) . . ?
C00X N00F H00F 126(5) . . ?
C013 N00G N00J 103.7(4) . . ?
C00W N00I N00F 104.6(5) . . ?
N00G N00J C00Y 111.9(4) . . ?
N00G N00J H00J 124(3) . . ?
C00Y N00J H00J 123(3) . . ?
N00Q N00K C010 112.1(4) . . ?
N00Q N00K H00K 126(3) . . ?
C010 N00K H00K 122(3) . . ?
O002 N00L O00R 126.1(6) . . ?
O002 N00L C00X 116.0(5) . . ?
O00R N00L C00X 118.0(6) . . ?
O003 N00M C011 117.2(4) . . ?
O004 N00M O003 125.4(4) . . ?
O004 N00M C011 117.4(4) . . ?
O00H N00P C015 115.3(6) . . ?
O00O N00P O00H 126.5(6) . . ?
O00O N00P C015 118.2(5) . . ?
C011 N00Q N00K 104.3(4) . . ?
O00E N00S O00N 127.3(6) . . ?
O00E N00S C014 116.5(5) . . ?
O00N N00S C014 116.1(6) . . ?
O007 N00U O008 126.0(4) . . ?
O007 N00U C00Y 116.5(4) . . ?
O008 N00U C00Y 117.4(4) . . ?
O009 N00V C016 117.6(5) . . ?
O00B N00V O009 124.8(6) . . ?
O00B N00V C016 117.6(5) . . ?
N00I C00W N00C 120.5(5) . . ?
N00I C00W C016 112.9(6) . . ?
C016 C00W N00C 126.6(6) . . ?
N00F C00X N00L 121.2(5) . . ?
N00F C00X C016 107.6(6) . . ?
C016 C00X N00L 131.2(6) . . ?
N00J C00Y N00U 121.5(4) . . ?
N00J C00Y C015 107.5(5) . . ?
C015 C00Y N00U 130.9(5) . . ?
O006 N00Z O00D 126.4(4) . . ?
O006 N00Z C010 117.7(4) . . ?
O00D N00Z C010 115.9(4) . . ?
N00K C010 N00Z 122.2(5) . . ?
N00K C010 C014 107.9(4) . . ?
C014 C010 N00Z 130.0(4) . . ?
N00Q C011 N00M 119.6(4) . . ?
N00Q C011 C014 113.1(5) . . ?
C014 C011 N00M 127.2(5) . . ?
O005 N012 O00A 126.3(4) . . ?
O005 N012 C013 117.5(4) . . ?
O00A N012 C013 116.2(4) . . ?
N00G C013 N012 118.7(5) . . ?
N00G C013 C015 113.3(4) . . ?
C015 C013 N012 127.9(4) . . ?
C010 C014 N00S 128.4(4) . . ?
C010 C014 C011 102.6(4) . . ?
C011 C014 N00S 129.0(5) . . ?
C00Y C015 N00P 127.7(5) . . ?
C00Y C015 C013 103.5(4) . . ?
C013 C015 N00P 128.8(4) . . ?
C00W C016 N00V 129.6(6) . . ?
C00X C016 N00V 127.6(5) . . ?
C00X C016 C00W 102.8(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
O001 N00C C00W N00I 179.2(4) . . . . ?
O001 N00C C00W C016 -0.9(7) . . . . ?
O002 N00L C00X N00F 176.5(4) . . . . ?
O002 N00L C00X C016 -4.5(8) . . . . ?
O003 N00M C011 N00Q -173.0(6) . . . . ?
O003 N00M C011 C014 11.0(9) . . . . ?
O004 N00M C011 N00Q 8.1(9) . . . . ?
O004 N00M C011 C014 -167.9(5) . . . . ?
O005 N012 C013 N00G 16.6(9) . . . . ?
O005 N012 C013 C015 -163.5(7) . . . . ?
O006 N00Z C010 N00K 9.0(11) . . . . ?
O006 N00Z C010 C014 -171.3(7) . . . . ?
O007 N00U C00Y N00J -173.6(5) . . . . ?
O007 N00U C00Y C015 6.5(9) . . . . ?
O008 N00U C00Y N00J 8.1(8) . . . . ?
O008 N00U C00Y C015 -171.8(6) . . . . ?
O009 N00V C016 C00W -94.5(6) . . . . ?
O009 N00V C016 C00X 85.4(6) . . . . ?
O00A N012 C013 N00G -163.5(5) . . . . ?
O00A N012 C013 C015 16.4(10) . . . . ?
O00B N00V C016 C00W 85.0(6) . . . . ?
O00B N00V C016 C00X -95.2(6) . . . . ?
N00C C00W C016 N00V 0.0(8) . . . . ?
N00C C00W C016 C00X -179.9(4) . . . . ?
O00D N00Z C010 N00K -172.3(6) . . . . ?
O00D N00Z C010 C014 7.4(11) . . . . ?
O00E N00S C014 C010 -109.7(7) . . . . ?
O00E N00S C014 C011 71.0(8) . . . . ?
N00F N00I C00W N00C -179.5(4) . . . . ?
N00F N00I C00W C016 0.6(5) . . . . ?
N00F C00X C016 N00V 179.5(4) . . . . ?
N00F C00X C016 C00W -0.6(5) . . . . ?
N00G N00J C00Y N00U -178.8(5) . . . . ?
N00G N00J C00Y C015 1.2(7) . . . . ?
N00G C013 C015 N00P 179.6(6) . . . . ?
N00G C013 C015 C00Y 0.0(7) . . . . ?
O00H N00P C015 C00Y -116.4(6) . . . . ?
O00H N00P C015 C013 64.1(8) . . . . ?
N00I N00F C00X N00L -179.7(4) . . . . ?
N00I N00F C00X C016 1.1(5) . . . . ?
N00I C00W C016 N00V 179.9(4) . . . . ?
N00I C00W C016 C00X 0.0(5) . . . . ?
N00J N00G C013 N012 -179.4(5) . . . . ?
N00J N00G C013 C015 0.7(6) . . . . ?
N00J C00Y C015 N00P 179.7(6) . . . . ?
N00J C00Y C015 C013 -0.7(7) . . . . ?
N00K N00Q C011 N00M -177.3(5) . . . . ?
N00K N00Q C011 C014 -0.7(8) . . . . ?
N00K C010 C014 N00S -179.0(6) . . . . ?
N00K C010 C014 C011 0.5(7) . . . . ?
N00L C00X C016 N00V 0.4(9) . . . . ?
N00L C00X C016 C00W -179.8(5) . . . . ?
N00M C011 C014 N00S -4.2(10) . . . . ?
N00M C011 C014 C010 176.4(6) . . . . ?
O00N N00S C014 C010 69.0(8) . . . . ?
O00N N00S C014 C011 -110.3(7) . . . . ?
O00O N00P C015 C00Y 63.1(8) . . . . ?
O00O N00P C015 C013 -116.4(7) . . . . ?
N00Q N00K C010 N00Z 178.8(6) . . . . ?
N00Q N00K C010 C014 -1.0(8) . . . . ?
N00Q C011 C014 N00S 179.6(6) . . . . ?
N00Q C011 C014 C010 0.2(7) . . . . ?
O00R N00L C00X N00F -2.4(7) . . . . ?
O00R N00L C00X C016 176.6(5) . . . . ?
O00T N00C C00W N00I -1.3(7) . . . . ?
O00T N00C C00W C016 178.6(5) . . . . ?
N00U C00Y C015 N00P -0.3(11) . . . . ?
N00U C00Y C015 C013 179.2(6) . . . . ?
C00X N00F N00I C00W -1.0(5) . . . . ?
N00Z C010 C014 N00S 1.3(12) . . . . ?
N00Z C010 C014 C011 -179.3(6) . . . . ?
C010 N00K N00Q C011 1.0(8) . . . . ?
N012 C013 C015 N00P -0.3(11) . . . . ?
N012 C013 C015 C00Y -179.9(6) . . . . ?
C013 N00G N00J C00Y -1.1(6) . . . . ?

_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_2tnp_p08_cc
_audit_block_doi                 10.5517/ccdc.csd.cc29gp2k
_database_code_depnum_ccdc_archive 'CCDC 2129268'
loop_
_audit_author_name
_audit_author_address
'Liu X.'
;The University of Edinburgh
United Kingdom
;
_audit_update_record             
;
2021-12-16 deposited with the CCDC.	2023-11-20 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT029_2tnp_p08_cc         
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.546 Why?
RESPONSE: high pressure data
;
_vrf_PLAT089_2tnp_p08_cc         
;
PROBLEM: Poor Data / Parameter Ratio (Zmax < 18) ........       2.36 Note
RESPONSE: high pressure data
;
_vrf_PLAT340_2tnp_p08_cc         
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.01667 Ang.
RESPONSE: high pressure data
;
# Added during the CSD deposition process: Thursday 16 December 2021 05:11 PM
# end Validation Reply Form

_audit_creation_date             2021-12-16
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
?
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '3(C3 N5 O6)'
_chemical_formula_sum            'C9 N15 O18'
_chemical_formula_weight         606.24
_chemical_absolute_configuration ?
_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'
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           9
_space_group_name_H-M_alt        'C 1 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'

_cell_length_a                   19.5713(11)
_cell_length_b                   7.6509(8)
_cell_length_c                   14.6982(9)
_cell_angle_alpha                90
_cell_angle_beta                 127.661(2)
_cell_angle_gamma                90
_cell_volume                     1742.3(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2276
_cell_measurement_temperature    298.4
_cell_measurement_theta_max      25.99
_cell_measurement_theta_min      2.81
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.226
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6498
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.311
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1212
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0326
_diffrn_reflns_av_unetI/netI     0.0414
_diffrn_reflns_Laue_measured_fraction_full 0.546
_diffrn_reflns_Laue_measured_fraction_max 0.503
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            4862
_diffrn_reflns_point_group_measured_fraction_full 0.510
_diffrn_reflns_point_group_measured_fraction_max 0.464
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.379
_diffrn_reflns_theta_min         2.629
_diffrn_ambient_temperature      298.4
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.546
_diffrn_measured_fraction_theta_max 0.503
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.844
_reflns_Friedel_fraction_full    0.473
_reflns_Friedel_fraction_max     0.425
_reflns_number_gt                1493
_reflns_number_total             1652
_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 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.172
_refine_diff_density_min         -0.193
_refine_diff_density_rms         0.044
_refine_ls_abs_structure_details 
;
 Flack x determined using 637 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -4.5(10)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    undef
_refine_ls_matrix_type           full
_refine_ls_number_parameters     379
_refine_ls_number_reflns         1652
_refine_ls_number_restraints     308
_refine_ls_R_factor_all          0.0458
_refine_ls_R_factor_gt           0.0399
_refine_ls_restrained_S_all      0.978
_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)+(0.0834P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1013
_refine_ls_wR_factor_ref         0.1053
_refine_special_details          ?
_olex2_refinement_description    
;
1. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
;
_atom_sites_solution_hydrogens   .
_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
O001 O 0.6634(5) 0.9097(15) 0.8870(6) 0.040(3) Uani 1 1 d . . . . .
N002 N 0.8116(5) 0.8874(16) 0.7907(7) 0.016(2) Uani 1 1 d . . . . .
O003 O 0.3342(4) 1.0488(14) 0.1516(6) 0.025(2) Uani 1 1 d . . . . .
O004 O 0.8603(4) 0.8322(11) 0.7714(5) 0.020(2) Uani 1 1 d . . . . .
N005 N 0.4869(5) 0.2419(16) 0.5983(7) 0.024(2) Uani 1 1 d . . . . .
N006 N 0.3370(5) -0.0084(16) 0.4216(7) 0.024(3) Uani 1 1 d . . . . .
O O 0.8216(4) 1.0172(14) 0.8450(7) 0.026(3) Uani 1 1 d . . . . .
O008 O 0.4927(4) 0.7985(13) 0.6652(5) 0.035(3) Uani 1 1 d . . . . .
O009 O 0.3317(5) -0.1573(15) 0.4503(6) 0.035(3) Uani 1 1 d . . . . .
C00A C 0.6638(5) 0.8319(17) 0.7391(7) 0.016(2) Uani 1 1 d . . . . .
O00B O 0.5065(4) 0.8429(14) 0.4297(5) 0.028(3) Uani 1 1 d . . . . .
N00C N 0.6465(5) 1.1737(17) 0.5602(6) 0.017(2) Uani 1 1 d . . . . .
O00D O 0.3147(4) 1.3345(14) 0.1256(6) 0.032(3) Uani 1 1 d . . . . .
O00E O 0.4642(4) 0.6211(13) 0.5302(6) 0.025(2) Uani 1 1 d . . . . .
C00F C 0.5643(6) 1.2247(17) 0.4521(8) 0.016(2) Uani 1 1 d . . . . .
O00G O 0.6873(4) 1.2887(13) 0.6306(6) 0.027(2) Uani 1 1 d . . . . .
O00H O 0.1315(4) 0.1893(12) 0.4251(5) 0.027(2) Uani 1 1 d . . . . .
C00I C 0.7305(6) 0.7943(17) 0.7333(7) 0.016(3) Uani 1 1 d . . . . .
N00J N 0.6302(4) 0.6339(14) 0.6124(6) 0.019(3) Uani 1 1 d . . . . .
N00K N 0.4666(4) 1.3935(15) 0.3287(6) 0.020(2) Uani 1 1 d . . . . .
O00L O 0.4913(4) 0.8671(14) 0.2722(5) 0.032(3) Uani 1 1 d . . . . .
O00M O 0.5376(4) 0.3554(14) 0.6634(6) 0.034(3) Uani 1 1 d . . . . .
O00N O 0.1688(5) -0.0196(16) 0.3626(7) 0.036(3) Uani 1 1 d . . . . .
O00O O 0.5051(4) 0.1111(13) 0.5662(5) 0.031(3) Uani 1 1 d . . . . .
N00P N 0.6614(5) 0.9599(18) 0.8065(7) 0.022(3) Uani 1 1 d . . . . .
N00Q N 0.4987(6) 0.9310(13) 0.3556(8) 0.020(2) Uani 1 1 d . . . . .
O00R O 0.6673(4) 1.0225(14) 0.5684(6) 0.022(2) Uani 1 1 d . . . . .
N00S N 0.3564(5) 1.2000(16) 0.1800(6) 0.018(3) Uani 1 1 d . . . . .
N00T N 0.2904(5) 0.3343(16) 0.5391(7) 0.023(3) Uani 1 1 d . . . . .
O00U O 0.6599(5) 1.1122(15) 0.7827(6) 0.032(3) Uani 1 1 d . . . . .
N00V N 0.7116(5) 0.6700(15) 0.6586(7) 0.019(3) Uani 1 1 d . . . . .
C00W C 0.5997(5) 0.7273(16) 0.6571(7) 0.014(3) Uani 1 1 d . . . . .
C00X C 0.3977(6) 0.2556(18) 0.5535(8) 0.021(3) Uani 1 1 d . . . . .
O00Y O 0.3457(5) 0.0259(13) 0.3476(6) 0.040(3) Uani 1 1 d . . . . .
C00Z C 0.5005(7) 1.1150(15) 0.3652(8) 0.015(2) Uani 1 1 d . . . . .
N010 N 0.3725(5) 0.3763(16) 0.5898(7) 0.026(3) Uani 1 1 d . . . . .
N1 N 0.5440(5) 1.3871(15) 0.4320(6) 0.020(2) Uani 1 1 d . . . . .
C2 C 0.4398(5) 1.2332(16) 0.2882(7) 0.017(3) Uani 1 1 d . . . . .
N3 N 0.5116(5) 0.7126(15) 0.6140(6) 0.019(3) Uani 1 1 d . . . . .
N4 N 0.1825(5) 0.1159(17) 0.4170(7) 0.021(2) Uani 1 1 d . . . . .
C5 C 0.3347(6) 0.1362(17) 0.4810(8) 0.019(3) Uani 1 1 d . . . . .
C6 C 0.2665(6) 0.1918(19) 0.4748(8) 0.018(3) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O001 N00P 1.221(12) . ?
N002 O004 1.224(10) . ?
N002 O 1.213(13) . ?
N002 C00I 1.451(14) . ?
O003 N00S 1.216(13) . ?
N005 O00M 1.223(14) . ?
N005 O00O 1.247(13) . ?
N005 C00X 1.444(12) . ?
N006 O009 1.241(14) . ?
N006 O00Y 1.228(12) . ?
N006 C5 1.426(15) . ?
O008 N3 1.214(11) . ?
C00A C00I 1.388(12) . ?
C00A N00P 1.415(16) . ?
C00A C00W 1.349(15) . ?
O00B N00Q 1.208(12) . ?
N00C C00F 1.464(12) . ?
N00C O00G 1.214(13) . ?
N00C O00R 1.207(14) . ?
O00D N00S 1.252(13) . ?
O00E N3 1.212(12) . ?
C00F C00Z 1.395(15) . ?
C00F N1 1.282(15) . ?
O00H N4 1.211(11) . ?
C00I N00V 1.323(15) . ?
N00J N00V 1.323(11) . ?
N00J C00W 1.333(12) . ?
N00K N1 1.339(10) . ?
N00K C2 1.323(15) . ?
O00L N00Q 1.244(12) . ?
O00N N4 1.235(16) . ?
N00P O00U 1.212(14) . ?
N00Q C00Z 1.413(13) . ?
N00S C2 1.445(12) . ?
N00T N010 1.334(11) . ?
N00T C6 1.327(16) . ?
C00W N3 1.434(10) . ?
C00X N010 1.305(16) . ?
C00X C5 1.373(16) . ?
C00Z C2 1.366(15) . ?
N4 C6 1.433(14) . ?
C5 C6 1.351(13) . ?

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
O004 N002 C00I 115.3(9) . . ?
O N002 O004 127.0(10) . . ?
O N002 C00I 117.5(8) . . ?
O00M N005 O00O 125.7(8) . . ?
O00M N005 C00X 118.8(11) . . ?
O00O N005 C00X 115.5(10) . . ?
O009 N006 C5 117.6(10) . . ?
O00Y N006 O009 125.7(11) . . ?
O00Y N006 C5 116.7(13) . . ?
C00I C00A N00P 128.4(10) . . ?
C00W C00A C00I 102.6(9) . . ?
C00W C00A N00P 128.8(8) . . ?
O00G N00C C00F 116.5(13) . . ?
O00R N00C C00F 116.3(9) . . ?
O00R N00C O00G 127.1(10) . . ?
C00Z C00F N00C 127.5(12) . . ?
N1 C00F N00C 119.2(10) . . ?
N1 C00F C00Z 113.2(9) . . ?
C00A C00I N002 126.8(10) . . ?
N00V C00I N002 119.2(8) . . ?
N00V C00I C00A 113.7(9) . . ?
N00V N00J C00W 113.3(8) . . ?
C2 N00K N1 109.8(10) . . ?
O001 N00P C00A 117.8(13) . . ?
O00U N00P O001 124.3(11) . . ?
O00U N00P C00A 117.9(10) . . ?
O00B N00Q O00L 122.9(11) . . ?
O00B N00Q C00Z 118.9(9) . . ?
O00L N00Q C00Z 118.1(8) . . ?
O003 N00S O00D 127.3(10) . . ?
O003 N00S C2 118.1(9) . . ?
O00D N00S C2 114.6(11) . . ?
C6 N00T N010 112.1(9) . . ?
N00J N00V C00I 102.4(8) . . ?
C00A C00W N3 130.7(9) . . ?
N00J C00W C00A 107.9(7) . . ?
N00J C00W N3 121.4(9) . . ?
N010 C00X N005 121.2(10) . . ?
N010 C00X C5 113.8(8) . . ?
C5 C00X N005 124.6(11) . . ?
C00F C00Z N00Q 130.1(9) . . ?
C2 C00Z C00F 101.5(10) . . ?
C2 C00Z N00Q 128.4(9) . . ?
C00X N010 N00T 103.3(9) . . ?
C00F N1 N00K 105.9(10) . . ?
N00K C2 N00S 121.9(10) . . ?
N00K C2 C00Z 109.6(9) . . ?
C00Z C2 N00S 128.4(11) . . ?
O008 N3 C00W 115.0(8) . . ?
O00E N3 O008 127.5(7) . . ?
O00E N3 C00W 117.4(8) . . ?
O00H N4 O00N 125.9(10) . . ?
O00H N4 C6 118.0(11) . . ?
O00N N4 C6 116.1(9) . . ?
C00X C5 N006 129.9(8) . . ?
C6 C5 N006 127.0(10) . . ?
C6 C5 C00X 103.0(10) . . ?
N00T C6 N4 122.2(9) . . ?
N00T C6 C5 107.9(10) . . ?
C5 C6 N4 129.9(12) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N002 C00I N00V N00J -171.2(9) . . . . ?
O003 N00S C2 N00K -175.8(6) . . . . ?
O003 N00S C2 C00Z 1.6(13) . . . . ?
O004 N002 C00I C00A -178.9(11) . . . . ?
O004 N002 C00I N00V -5.6(16) . . . . ?
N005 C00X N010 N00T -173.2(10) . . . . ?
N005 C00X C5 N006 -10(2) . . . . ?
N005 C00X C5 C6 172.6(10) . . . . ?
N006 C5 C6 N00T -177.3(13) . . . . ?
N006 C5 C6 N4 6(2) . . . . ?
O N002 C00I C00A -4.1(19) . . . . ?
O N002 C00I N00V 169.1(13) . . . . ?
O009 N006 C5 C00X 113.5(14) . . . . ?
O009 N006 C5 C6 -69.1(16) . . . . ?
C00A C00I N00V N00J 2.9(15) . . . . ?
C00A C00W N3 O008 -6.3(17) . . . . ?
C00A C00W N3 O00E 171.9(11) . . . . ?
O00B N00Q C00Z C00F 58.4(14) . . . . ?
O00B N00Q C00Z C2 -123.9(10) . . . . ?
N00C C00F C00Z N00Q -2.4(15) . . . . ?
N00C C00F C00Z C2 179.4(7) . . . . ?
N00C C00F N1 N00K -179.8(7) . . . . ?
O00D N00S C2 N00K 4.1(11) . . . . ?
O00D N00S C2 C00Z -178.6(8) . . . . ?
C00F C00Z C2 N00K -0.6(10) . . . . ?
C00F C00Z C2 N00S -178.2(7) . . . . ?
O00G N00C C00F C00Z -170.3(9) . . . . ?
O00G N00C C00F N1 7.4(11) . . . . ?
O00H N4 C6 N00T 2.5(19) . . . . ?
O00H N4 C6 C5 179.0(12) . . . . ?
C00I C00A N00P O001 -109.3(14) . . . . ?
C00I C00A N00P O00U 68.6(16) . . . . ?
C00I C00A C00W N00J 2.2(12) . . . . ?
C00I C00A C00W N3 -175.0(11) . . . . ?
N00J C00W N3 O008 176.8(10) . . . . ?
N00J C00W N3 O00E -5.0(16) . . . . ?
O00L N00Q C00Z C00F -119.9(10) . . . . ?
O00L N00Q C00Z C2 57.9(13) . . . . ?
O00M N005 C00X N010 -6.8(17) . . . . ?
O00M N005 C00X C5 -179.2(11) . . . . ?
O00N N4 C6 N00T -177.8(15) . . . . ?
O00N N4 C6 C5 -1(2) . . . . ?
O00O N005 C00X N010 172.9(11) . . . . ?
O00O N005 C00X C5 0.5(16) . . . . ?
N00P C00A C00I N002 -4(2) . . . . ?
N00P C00A C00I N00V -177.9(12) . . . . ?
N00P C00A C00W N00J 176.8(13) . . . . ?
N00P C00A C00W N3 0(2) . . . . ?
N00Q C00Z C2 N00K -178.9(7) . . . . ?
N00Q C00Z C2 N00S 3.5(15) . . . . ?
O00R N00C C00F C00Z 11.4(12) . . . . ?
O00R N00C C00F N1 -170.8(7) . . . . ?
N00V N00J C00W C00A -0.6(13) . . . . ?
N00V N00J C00W N3 176.9(10) . . . . ?
C00W C00A C00I N002 170.3(10) . . . . ?
C00W C00A C00I N00V -3.3(15) . . . . ?
C00W C00A N00P O001 77.4(15) . . . . ?
C00W C00A N00P O00U -104.6(15) . . . . ?
C00W N00J N00V C00I -1.4(14) . . . . ?
C00X C5 C6 N00T 0.6(15) . . . . ?
C00X C5 C6 N4 -176.3(12) . . . . ?
O00Y N006 C5 C00X -65.2(16) . . . . ?
O00Y N006 C5 C6 112.1(13) . . . . ?
C00Z C00F N1 N00K -1.8(9) . . . . ?
N010 N00T C6 N4 176.5(9) . . . . ?
N010 N00T C6 C5 -0.7(17) . . . . ?
N010 C00X C5 N006 177.5(12) . . . . ?
N010 C00X C5 C6 -0.3(14) . . . . ?
N1 C00F C00Z N00Q 179.7(8) . . . . ?
N1 C00F C00Z C2 1.5(10) . . . . ?
N1 N00K C2 N00S 177.4(7) . . . . ?
N1 N00K C2 C00Z -0.4(9) . . . . ?
C2 N00K N1 C00F 1.3(8) . . . . ?
C5 C00X N010 N00T -0.1(14) . . . . ?
C6 N00T N010 C00X 0.5(15) . . . . ?

_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_2tnp_p09
_audit_block_doi                 10.5517/ccdc.csd.cc29gp3l
_database_code_depnum_ccdc_archive 'CCDC 2129269'
loop_
_audit_author_name
_audit_author_address
'Liu X.'
;The University of Edinburgh
United Kingdom
;
_audit_update_record             
;
2021-12-16 deposited with the CCDC.	2023-11-20 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT029_2tnp_p09            
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.549 Why?
RESPONSE: high pressure data
;
_vrf_PLAT089_2tnp_p09            
;
PROBLEM: Poor Data / Parameter Ratio (Zmax < 18) ........       2.32 Note
RESPONSE: high pressure data
;
_vrf_PLAT340_2tnp_p09            
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.01667 Ang.
RESPONSE: high pressure data
;
# Added during the CSD deposition process: Thursday 16 December 2021 05:11 PM
# end Validation Reply Form

_audit_creation_date             2021-12-16
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
?
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '3(C3 N5 O6)'
_chemical_formula_sum            'C9 H0.25 N15 O18'
_chemical_formula_weight         606.49
_chemical_absolute_configuration ?
_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'
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'
H H 0.0000 0.0000 '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           9
_space_group_name_H-M_alt        'C 1 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'

_cell_length_a                   19.3994(12)
_cell_length_b                   7.5957(8)
_cell_length_c                   14.5289(16)
_cell_angle_alpha                90
_cell_angle_beta                 127.637(3)
_cell_angle_gamma                90
_cell_volume                     1695.3(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2420
_cell_measurement_temperature    298.4
_cell_measurement_theta_max      26.23
_cell_measurement_theta_min      2.85
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.232
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6454
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0908 before and 0.0410 after correction.
The Ratio of minimum to maximum transmission is 0.8658.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.376
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1213
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0246
_diffrn_reflns_av_unetI/netI     0.0335
_diffrn_reflns_Laue_measured_fraction_full 0.549
_diffrn_reflns_Laue_measured_fraction_max 0.507
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            4436
_diffrn_reflns_point_group_measured_fraction_full 0.508
_diffrn_reflns_point_group_measured_fraction_max 0.464
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.367
_diffrn_reflns_theta_min         2.652
_diffrn_ambient_temperature      298.4
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.549
_diffrn_measured_fraction_theta_max 0.507
_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         0.826
_reflns_Friedel_fraction_full    0.468
_reflns_Friedel_fraction_max     0.420
_reflns_number_gt                1481
_reflns_number_total             1607
_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 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.209
_refine_diff_density_min         -0.212
_refine_diff_density_rms         0.047
_refine_ls_abs_structure_details 
;
 Flack x determined using 634 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -1.2(10)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_hydrogen_treatment    undef
_refine_ls_matrix_type           full
_refine_ls_number_parameters     379
_refine_ls_number_reflns         1607
_refine_ls_number_restraints     308
_refine_ls_R_factor_all          0.0412
_refine_ls_R_factor_gt           0.0368
_refine_ls_restrained_S_all      0.994
_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)+(0.0781P)²+0.6967P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0993
_refine_ls_wR_factor_ref         0.1025
_refine_special_details          ?
_olex2_refinement_description    
;
1. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
;
_atom_sites_solution_hydrogens   .
_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
O001 O 1.0303(4) 0.8090(12) 0.8251(6) 0.025(2) Uani 1 1 d . . . . .
O002 O 0.4995(5) -0.1166(15) 0.4671(6) 0.031(3) Uani 1 1 d . . . . .
O003 O 0.9921(5) 1.0242(16) 0.8838(7) 0.034(3) Uani 1 1 d . . . . .
N004 N 0.3488(5) 0.1122(16) 0.4588(7) 0.018(3) Uani 1 1 d . . . . .
C005 C 0.4969(5) 0.1684(16) 0.5092(7) 0.014(2) Uani 1 1 d . . . . .
N006 N 0.0131(4) 0.6743(18) 0.1867(6) 0.018(2) Uani 1 1 d . . . . .
O007 O 0.6973(4) 0.3796(13) 0.7195(6) 0.026(3) Uani 1 1 d . . . . .
O008 O 0.3478(4) 0.8321(14) 0.6274(6) 0.030(2) Uani 1 1 d . . . . .
N009 N 0.8712(5) 0.6630(15) 0.7112(7) 0.021(3) Uani 1 1 d . . . . .
C00A C 0.5609(6) 0.2749(17) 0.5905(7) 0.016(3) Uani 1 1 d . . . . .
O00B O 0.6694(4) 0.1970(13) 0.5853(5) 0.031(3) Uani 1 1 d . . . . .
N00C N 0.6726(5) 0.7564(15) 0.6502(7) 0.020(2) Uani 1 1 d . . . . .
O00D O 0.3281(4) 0.5473(13) 0.5994(6) 0.023(2) Uani 1 1 d . . . . .
C00G C 0.4293(5) 0.2046(18) 0.5150(8) 0.016(3) Uani 1 1 d . . . . .
O00H O -0.0070(4) 0.5216(14) 0.1790(6) 0.021(2) Uani 1 1 d . . . . .
O00I O 0.1704(4) 0.3645(13) 0.4775(5) 0.031(3) Uani 1 1 d . . . . .
C00J C 0.0957(5) 0.7231(17) 0.2961(7) 0.016(2) Uani 1 1 d . . . . .
N00L N 0.1624(6) 0.4287(13) 0.3938(8) 0.020(2) Uani 1 1 d . . . . .
O00M O 0.2989(4) 0.1689(11) 0.4774(6) 0.021(2) Uani 1 1 d . . . . .
O00N O 0.1533(4) 0.3408(14) 0.3172(5) 0.026(2) Uani 1 1 d . . . . .
N N 0.5301(4) 0.3698(15) 0.6356(7) 0.021(3) Uani 1 1 d . . . . .
O00P O 0.6211(4) 0.6432(14) 0.5840(6) 0.032(3) Uani 1 1 d . . . . .
N00Q N 0.4994(5) 0.0350(18) 0.4413(7) 0.022(3) Uani 1 1 d . . . . .
O00R O 0.6542(4) 0.8900(13) 0.6816(5) 0.029(3) Uani 1 1 d . . . . .
O00T O 0.3380(5) -0.0226(14) 0.4050(7) 0.027(3) Uani 1 1 d . . . . .
N00U N 0.7876(5) 0.6228(16) 0.6589(6) 0.024(3) Uani 1 1 d . . . . .
N00V N 0.3053(5) 0.6999(17) 0.5714(7) 0.019(3) Uani 1 1 d . . . . .
C00W C 0.1594(7) 0.6147(16) 0.3831(9) 0.015(2) Uani 1 1 d . . . . .
O00X O 0.5000(5) 0.0858(15) 0.3625(6) 0.037(3) Uani 1 1 d . . . . .
N00Y N 0.6499(5) 0.2870(15) 0.6354(7) 0.020(3) Uani 1 1 d . . . . .
O00Z O -0.0280(4) 0.7907(13) 0.1162(6) 0.026(2) Uani 1 1 d . . . . .
N010 N 0.9790(5) 0.8857(17) 0.8312(7) 0.020(2) Uani 1 1 d . . . . .
N1 N 0.1940(4) 0.8958(15) 0.4221(6) 0.019(2) Uani 1 1 d . . . . .
N2 N 0.1158(5) 0.8904(15) 0.3175(7) 0.020(2) Uani 1 1 d . . . . .
N3 N 0.4485(5) 0.3318(15) 0.5904(7) 0.021(3) Uani 1 1 d . . . . .
C4 C 0.8940(6) 0.8088(19) 0.7731(8) 0.019(3) Uani 1 1 d . . . . .
C5 C 0.2210(5) 0.7336(16) 0.4620(7) 0.017(3) Uani 1 1 d . . . . .
C6 C 0.7623(6) 0.7443(18) 0.6961(8) 0.020(3) Uani 1 1 d . . . . .
C1 C 0.8255(6) 0.8662(18) 0.7679(8) 0.020(3) Uani 1 1 d . . . . .
O1 O 0.8303(5) 1.1609(15) 0.7993(6) 0.032(3) Uani 1 1 d . . . . .
O2 O 0.8138(4) 0.9778(14) 0.9022(6) 0.040(3) Uani 1 1 d . . . . .
N4 N 0.8231(5) 1.0122(16) 0.8269(7) 0.022(3) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O001 N010 1.202(11) . ?
O002 N00Q 1.211(15) . ?
O003 N010 1.232(16) . ?
N004 C00G 1.429(14) . ?
N004 O00M 1.231(10) . ?
N004 O00T 1.227(14) . ?
C005 C00A 1.342(15) . ?
C005 C00G 1.392(13) . ?
C005 N00Q 1.436(16) . ?
N006 O00H 1.207(14) . ?
N006 C00J 1.456(12) . ?
N006 O00Z 1.212(13) . ?
O007 N00Y 1.209(13) . ?
O008 N00V 1.238(13) . ?
N009 N00U 1.340(11) . ?
N009 C4 1.321(16) . ?
C00A N 1.337(13) . ?
C00A N00Y 1.428(11) . ?
O00B N00Y 1.215(11) . ?
N00C O00P 1.220(14) . ?
N00C O00R 1.251(12) . ?
N00C C6 1.436(11) . ?
O00D N00V 1.218(13) . ?
C00G N3 1.332(16) . ?
O00I N00L 1.229(11) . ?
C00J C00W 1.377(15) . ?
C00J N2 1.310(15) . ?
N00L O00N 1.214(12) . ?
N00L C00W 1.419(13) . ?
N N3 1.323(11) . ?
N00Q O00X 1.216(12) . ?
N00U C6 1.308(15) . ?
N00V C5 1.447(12) . ?
C00W C5 1.372(15) . ?
N010 C4 1.440(13) . ?
N1 N2 1.341(9) . ?
N1 C5 1.325(15) . ?
C4 C1 1.356(13) . ?
C6 C1 1.374(17) . ?
C1 N4 1.420(16) . ?
O1 N4 1.235(14) . ?
O2 N4 1.239(12) . ?

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
O00M N004 C00G 115.7(9) . . ?
O00T N004 C00G 118.4(9) . . ?
O00T N004 O00M 125.5(10) . . ?
C00A C005 C00G 103.2(9) . . ?
C00A C005 N00Q 128.9(8) . . ?
C00G C005 N00Q 127.6(10) . . ?
O00H N006 C00J 115.1(9) . . ?
O00H N006 O00Z 127.8(10) . . ?
O00Z N006 C00J 117.0(13) . . ?
C4 N009 N00U 111.3(9) . . ?
C005 C00A N00Y 130.7(10) . . ?
N C00A C005 107.8(7) . . ?
N C00A N00Y 121.3(9) . . ?
O00P N00C O00R 125.5(8) . . ?
O00P N00C C6 119.8(10) . . ?
O00R N00C C6 114.7(9) . . ?
C005 C00G N004 127.6(10) . . ?
N3 C00G N004 119.0(8) . . ?
N3 C00G C005 113.1(9) . . ?
C00W C00J N006 128.5(13) . . ?
N2 C00J N006 118.4(10) . . ?
N2 C00J C00W 113.1(9) . . ?
O00I N00L C00W 118.4(8) . . ?
O00N N00L O00I 123.2(11) . . ?
O00N N00L C00W 118.3(8) . . ?
N3 N C00A 113.4(8) . . ?
O002 N00Q C005 116.9(10) . . ?
O002 N00Q O00X 126.5(12) . . ?
O00X N00Q C005 116.6(13) . . ?
C6 N00U N009 103.6(9) . . ?
O008 N00V C5 115.5(12) . . ?
O00D N00V O008 126.4(10) . . ?
O00D N00V C5 118.1(9) . . ?
C00J C00W N00L 130.5(10) . . ?
C5 C00W C00J 102.1(11) . . ?
C5 C00W N00L 127.4(9) . . ?
O007 N00Y C00A 117.4(8) . . ?
O007 N00Y O00B 127.6(8) . . ?
O00B N00Y C00A 115.0(9) . . ?
O001 N010 O003 126.3(10) . . ?
O001 N010 C4 117.7(11) . . ?
O003 N010 C4 116.0(9) . . ?
C5 N1 N2 109.8(10) . . ?
C00J N2 N1 105.4(10) . . ?
N N3 C00G 102.4(8) . . ?
N009 C4 N010 121.8(9) . . ?
N009 C4 C1 108.8(10) . . ?
C1 C4 N010 129.4(12) . . ?
C00W C5 N00V 128.7(11) . . ?
N1 C5 N00V 121.6(10) . . ?
N1 C5 C00W 109.7(9) . . ?
N00U C6 N00C 120.5(10) . . ?
N00U C6 C1 113.8(8) . . ?
C1 C6 N00C 125.2(11) . . ?
C4 C1 C6 102.5(10) . . ?
C4 C1 N4 127.6(10) . . ?
C6 C1 N4 129.9(8) . . ?
O1 N4 C1 117.7(10) . . ?
O1 N4 O2 125.9(11) . . ?
O2 N4 C1 116.4(13) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O001 N010 C4 N009 -2.6(19) . . . . ?
O001 N010 C4 C1 179.0(11) . . . . ?
O003 N010 C4 N009 178.1(14) . . . . ?
O003 N010 C4 C1 0(2) . . . . ?
N004 C00G N3 N 171.9(9) . . . . ?
C005 C00A N N3 0.9(13) . . . . ?
C005 C00A N00Y O007 -170.7(12) . . . . ?
C005 C00A N00Y O00B 7.2(17) . . . . ?
C005 C00G N3 N -2.7(16) . . . . ?
N006 C00J C00W N00L -2.3(16) . . . . ?
N006 C00J C00W C5 179.4(7) . . . . ?
N006 C00J N2 N1 -179.8(6) . . . . ?
O008 N00V C5 C00W -178.7(8) . . . . ?
O008 N00V C5 N1 4.0(11) . . . . ?
N009 N00U C6 N00C 174.0(10) . . . . ?
N009 N00U C6 C1 2.1(14) . . . . ?
N009 C4 C1 C6 -1.5(15) . . . . ?
N009 C4 C1 N4 176.1(13) . . . . ?
C00A C005 C00G N004 -170.8(11) . . . . ?
C00A C005 C00G N3 3.2(15) . . . . ?
C00A C005 N00Q O002 106.0(14) . . . . ?
C00A C005 N00Q O00X -75.0(15) . . . . ?
C00A N N3 C00G 1.1(14) . . . . ?
N00C C6 C1 C4 -171.9(10) . . . . ?
N00C C6 C1 N4 11(2) . . . . ?
O00D N00V C5 C00W 1.7(13) . . . . ?
O00D N00V C5 N1 -175.6(6) . . . . ?
C00G C005 C00A N -2.3(12) . . . . ?
C00G C005 C00A N00Y 172.6(11) . . . . ?
C00G C005 N00Q O002 -66.3(15) . . . . ?
C00G C005 N00Q O00X 112.7(13) . . . . ?
O00H N006 C00J C00W 11.2(12) . . . . ?
O00H N006 C00J N2 -170.2(7) . . . . ?
O00I N00L C00W C00J -120.3(11) . . . . ?
O00I N00L C00W C5 57.6(13) . . . . ?
C00J C00W C5 N00V -177.8(7) . . . . ?
C00J C00W C5 N1 -0.2(10) . . . . ?
N00L C00W C5 N00V 3.8(15) . . . . ?
N00L C00W C5 N1 -178.6(7) . . . . ?
O00M N004 C00G C005 179.8(11) . . . . ?
O00M N004 C00G N3 6.1(16) . . . . ?
O00N N00L C00W C00J 56.7(14) . . . . ?
O00N N00L C00W C5 -125.4(10) . . . . ?
N C00A N00Y O007 3.6(17) . . . . ?
N C00A N00Y O00B -178.5(10) . . . . ?
O00P N00C C6 N00U 6.7(17) . . . . ?
O00P N00C C6 C1 177.6(11) . . . . ?
N00Q C005 C00A N -176.1(13) . . . . ?
N00Q C005 C00A N00Y -1(2) . . . . ?
N00Q C005 C00G N004 3(2) . . . . ?
N00Q C005 C00G N3 177.1(12) . . . . ?
O00R N00C C6 N00U -171.6(11) . . . . ?
O00R N00C C6 C1 -0.7(15) . . . . ?
O00T N004 C00G C005 5.7(19) . . . . ?
O00T N004 C00G N3 -168.0(14) . . . . ?
N00U N009 C4 N010 -175.7(9) . . . . ?
N00U N009 C4 C1 2.9(16) . . . . ?
N00U C6 C1 C4 -0.4(14) . . . . ?
N00U C6 C1 N4 -178.0(12) . . . . ?
C00W C00J N2 N1 -1.1(9) . . . . ?
N00Y C00A N N3 -174.6(10) . . . . ?
O00Z N006 C00J C00W -170.6(9) . . . . ?
O00Z N006 C00J N2 7.9(11) . . . . ?
N010 C4 C1 C6 177.0(12) . . . . ?
N010 C4 C1 N4 -5(2) . . . . ?
N2 C00J C00W N00L 179.1(8) . . . . ?
N2 C00J C00W C5 0.8(10) . . . . ?
N2 N1 C5 N00V 177.4(7) . . . . ?
N2 N1 C5 C00W -0.4(9) . . . . ?
C4 N009 N00U C6 -3.0(15) . . . . ?
C4 C1 N4 O1 67.0(16) . . . . ?
C4 C1 N4 O2 -112.9(13) . . . . ?
C5 N1 N2 C00J 0.9(8) . . . . ?
C6 C1 N4 O1 -116.0(14) . . . . ?
C6 C1 N4 O2 64.0(17) . . . . ?

_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_2tnp_p04
_audit_block_doi                 10.5517/ccdc.csd.cc29gp6p
_database_code_depnum_ccdc_archive 'CCDC 2129272'
loop_
_audit_author_name
_audit_author_address
'Liu X.'
;The University of Edinburgh
United Kingdom
;
_audit_update_record             
;
2021-12-16 deposited with the CCDC.	2023-11-20 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT029_2tnp_p04            
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.549 Why?
RESPONSE: high pressure data
;
_vrf_PLAT088_2tnp_p04            
;
PROBLEM: Poor Data / Parameter Ratio ....................       5.29 Note
RESPONSE: high pressure data
;
_vrf_PLAT110_2tnp_p04            
;
PROBLEM: ADDSYM Detects Potential Lattice Translation ...          ? Check
RESPONSE: the nature with this crystal - if the data quality is not good enough to clear locate H atoms, stuture falls into Pseudo sysmetry C2/c ( DOI: 10.1002/anie.201006000)
;
_vrf_PLAT112_2tnp_p04            
;
PROBLEM: ADDSYM Detects New (Pseudo) Symm. Elem         I        100 %Fit
RESPONSE: the nature with this crystal - if the data quality is not good enough to clear locate H atoms, stuture falls into Pseudo sysmetry C2/c ( DOI: 10.1002/anie.201006000)
;
_vrf_PLAT113_2tnp_p04            
;
PROBLEM: ADDSYM Suggests Possible Pseudo/New  Space Group       I2/a Check
RESPONSE: the nature with this crystal - if the data quality is not good enough to clear locate H atoms, stuture falls into Pseudo sysmetry C2/c ( DOI: 10.1002/anie.201006000)
;
# Added during the CSD deposition process: Thursday 16 December 2021 05:11 PM
# end Validation Reply Form

_audit_creation_date             2021-12-16
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
?
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '3(C3 H N5 O6)'
_chemical_formula_sum            'C9 H3 N15 O18'
_chemical_formula_weight         609.26
_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                   14.7836(11)
_cell_length_b                   8.0383(8)
_cell_length_c                   16.8670(12)
_cell_angle_alpha                90
_cell_angle_beta                 92.078(4)
_cell_angle_gamma                90
_cell_volume                     2003.1(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2947
_cell_measurement_temperature    300.8
_cell_measurement_theta_max      25.02
_cell_measurement_theta_min      2.76
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.197
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6758
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.020
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1224
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0445
_diffrn_reflns_av_unetI/netI     0.0483
_diffrn_reflns_Laue_measured_fraction_full 0.549
_diffrn_reflns_Laue_measured_fraction_max 0.506
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            10642
_diffrn_reflns_point_group_measured_fraction_full 0.549
_diffrn_reflns_point_group_measured_fraction_max 0.506
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.361
_diffrn_reflns_theta_min         2.417
_diffrn_ambient_temperature      300.8
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.549
_diffrn_measured_fraction_theta_max 0.506
_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                1435
_reflns_number_total             2068
_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 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.156
_refine_diff_density_min         -0.192
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     391
_refine_ls_number_reflns         2068
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0767
_refine_ls_R_factor_gt           0.0445
_refine_ls_restrained_S_all      1.051
_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)+(0.0689P)²+0.6636P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1081
_refine_ls_wR_factor_ref         0.1236
_refine_special_details          ?
_olex2_refinement_description    
;
;
_atom_sites_solution_hydrogens   difmap
_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
O001 O 0.68330(17) 0.5961(4) 0.65058(16) 0.0438(8) Uani 1 1 d . . . . .
O002 O 0.52259(16) 0.4964(4) 0.81225(14) 0.0422(8) Uani 1 1 d . . . . .
O003 O 0.66165(15) 0.4209(3) 0.83384(14) 0.0410(8) Uani 1 1 d . . . . .
O004 O 0.83179(18) 0.5986(4) 0.35438(17) 0.0504(9) Uani 1 1 d . . . . .
N005 N 0.7607(2) 0.9369(5) 0.4645(2) 0.0249(8) Uani 1 1 d . . . . .
O006 O 0.92534(18) 0.1078(5) 0.51046(17) 0.0535(9) Uani 1 1 d . . . . .
O007 O 0.56332(18) 0.1273(4) 0.48087(16) 0.0481(9) Uani 1 1 d . . . . .
N008 N 0.72716(18) 0.9416(4) 0.53643(19) 0.0253(8) Uani 1 1 d . . . . .
O009 O 0.83648(15) 0.4100(4) 0.15811(14) 0.0509(9) Uani 1 1 d . . . . .
O00A O 1.03317(16) 0.2855(4) 0.49459(14) 0.0521(9) Uani 1 1 d . . . . .
O00B O 0.98032(16) 0.4590(4) 0.17610(15) 0.0480(9) Uani 1 1 d . . . . .
O00C O 1.12223(16) 0.2969(4) 0.34059(16) 0.0575(10) Uani 1 1 d . . . . .
O00D O 0.45691(16) 0.3078(4) 0.49889(14) 0.0507(9) Uani 1 1 d . . . . .
N00E N 0.6397(2) 0.2032(5) 0.62523(18) 0.0259(8) Uani 1 1 d . . . . .
N00F N 0.84370(17) 0.2081(4) 0.37514(16) 0.0269(8) Uani 1 1 d . . . . .
N00G N 0.8147(2) 0.7428(5) 0.3673(2) 0.0317(9) Uani 1 1 d . . . . .
O00H O 0.69085(17) 0.4186(4) 0.48385(17) 0.0521(9) Uani 1 1 d . . . . .
N00I N 0.6871(2) 0.7427(5) 0.6347(2) 0.0314(9) Uani 1 1 d . . . . .
O00J O 0.4429(2) 0.5962(5) 0.65576(18) 0.0637(11) Uani 1 1 d . . . . .
N00K N 0.65993(18) 0.2516(4) 0.69890(16) 0.0268(8) Uani 1 1 d . . . . .
O00L O 0.82900(18) 0.4344(4) 0.52700(17) 0.0579(9) Uani 1 1 d . . . . .
N00M N 0.90774(18) 0.4062(4) 0.19649(16) 0.0299(8) Uani 1 1 d . . . . .
N00N N 0.83113(18) 0.2613(4) 0.30072(16) 0.0250(8) Uani 1 1 d . . . . .
N00O N 1.0611(2) 0.3991(5) 0.33338(18) 0.0363(10) Uani 1 1 d . . . . .
N00P N 0.4389(2) 0.4461(5) 0.65711(18) 0.0364(10) Uani 1 1 d . . . . .
N00Q N 0.59164(17) 0.4259(4) 0.79402(16) 0.0258(8) Uani 1 1 d . . . . .
O00R O 0.8264(2) 0.8593(4) 0.32262(17) 0.0567(9) Uani 1 1 d . . . . .
N00S N 0.9647(2) 0.2110(5) 0.47304(18) 0.0343(9) Uani 1 1 d . . . . .
O00T O 1.0706(2) 0.5464(5) 0.32625(18) 0.0644(13) Uani 1 1 d . . . . .
O00U O 0.6650(2) 0.8558(5) 0.67718(18) 0.0609(10) Uani 1 1 d . . . . .
N00V N 0.75798(18) 0.4958(5) 0.50430(15) 0.0323(9) Uani 1 1 d . . . . .
O00W O 0.37150(17) 0.3607(4) 0.65604(17) 0.0624(10) Uani 1 1 d . . . . .
N00X N 0.5246(2) 0.2292(5) 0.51965(18) 0.0329(9) Uani 1 1 d . . . . .
C00Y C 0.5601(2) 0.2636(5) 0.5986(2) 0.0243(9) Uani 1 1 d . . . . .
C00Z C 0.7531(2) 0.6754(5) 0.5019(2) 0.0208(9) Uani 1 1 d . . . . .
C010 C 0.59040(19) 0.3449(5) 0.71839(19) 0.0213(9) Uani 1 1 d . . . . .
C011 C 0.7778(2) 0.7807(5) 0.4421(2) 0.0227(10) Uani 1 1 d . . . . .
C012 C 0.9277(2) 0.2513(4) 0.39459(19) 0.0224(9) Uani 1 1 d . . . . .
C013 C 0.9054(2) 0.3369(5) 0.27396(18) 0.0223(9) Uani 1 1 d . . . . .
C014 C 0.5248(2) 0.3572(5) 0.65750(19) 0.0239(9) Uani 1 1 d . . . . .
C015 C 0.9702(2) 0.3324(5) 0.33408(19) 0.0261(9) Uani 1 1 d . . . . .
C016 C 0.7216(2) 0.7857(5) 0.5590(2) 0.0225(9) Uani 1 1 d . . . . .
H00E H 0.675(2) 0.131(5) 0.598(2) 0.022(9) Uiso 1 1 d . . . . .
H00N H 0.773(3) 0.263(5) 0.272(2) 0.074(13) Uiso 1 1 d . . . . .
H005 H 0.779(3) 1.031(7) 0.432(3) 0.087(17) 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
O001 N00I 1.210(4) . ?
O002 N00Q 1.217(3) . ?
O003 N00Q 1.214(3) . ?
O004 N00G 1.207(4) . ?
N005 N008 1.328(5) . ?
N005 C011 1.338(5) . ?
N005 H005 0.99(5) . ?
O006 N00S 1.205(4) . ?
O007 N00X 1.206(4) . ?
N008 C016 1.313(5) . ?
O009 N00M 1.217(3) . ?
O00A N00S 1.220(3) . ?
O00B N00M 1.215(4) . ?
O00C N00O 1.224(4) . ?
O00D N00X 1.223(4) . ?
N00E N00K 1.326(4) . ?
N00E C00Y 1.336(4) . ?
N00E H00E 0.91(3) . ?
N00F N00N 1.333(4) . ?
N00F C012 1.319(4) . ?
N00G O00R 1.219(5) . ?
N00G C011 1.426(5) . ?
O00H N00V 1.210(4) . ?
N00I O00U 1.209(5) . ?
N00I C016 1.434(5) . ?
O00J N00P 1.208(4) . ?
N00K C010 1.323(4) . ?
O00L N00V 1.210(3) . ?
N00M C013 1.422(4) . ?
N00N C013 1.348(4) . ?
N00N H00N 0.97(4) . ?
N00O O00T 1.198(4) . ?
N00O C015 1.448(4) . ?
N00P O00W 1.210(4) . ?
N00P C014 1.456(4) . ?
N00Q C010 1.432(4) . ?
N00S C012 1.450(4) . ?
N00V C00Z 1.446(5) . ?
N00X C00Y 1.440(4) . ?
C00Y C014 1.365(5) . ?
C00Z C011 1.376(6) . ?
C00Z C016 1.401(5) . ?
C010 C014 1.391(4) . ?
C012 C015 1.381(5) . ?
C013 C015 1.369(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
N008 N005 C011 111.4(3) . . ?
N008 N005 H005 128(4) . . ?
C011 N005 H005 120(4) . . ?
C016 N008 N005 105.5(3) . . ?
N00K N00E C00Y 112.0(3) . . ?
N00K N00E H00E 122.7(18) . . ?
C00Y N00E H00E 125.1(18) . . ?
C012 N00F N00N 104.3(3) . . ?
O004 N00G O00R 126.2(4) . . ?
O004 N00G C011 117.0(4) . . ?
O00R N00G C011 116.8(4) . . ?
O001 N00I C016 116.9(4) . . ?
O00U N00I O001 125.8(4) . . ?
O00U N00I C016 117.3(5) . . ?
C010 N00K N00E 104.4(2) . . ?
O009 N00M C013 116.7(3) . . ?
O00B N00M O009 126.7(3) . . ?
O00B N00M C013 116.6(2) . . ?
N00F N00N C013 111.9(3) . . ?
N00F N00N H00N 124(2) . . ?
C013 N00N H00N 123(2) . . ?
O00C N00O C015 115.6(4) . . ?
O00T N00O O00C 125.7(4) . . ?
O00T N00O C015 118.6(3) . . ?
O00J N00P O00W 127.4(4) . . ?
O00J N00P C014 116.5(3) . . ?
O00W N00P C014 116.1(4) . . ?
O002 N00Q C010 116.9(2) . . ?
O003 N00Q O002 125.6(3) . . ?
O003 N00Q C010 117.5(3) . . ?
O006 N00S O00A 126.4(3) . . ?
O006 N00S C012 117.3(3) . . ?
O00A N00S C012 116.4(3) . . ?
O00H N00V C00Z 117.6(3) . . ?
O00L N00V O00H 125.1(4) . . ?
O00L N00V C00Z 117.3(3) . . ?
O007 N00X O00D 126.5(3) . . ?
O007 N00X C00Y 117.9(3) . . ?
O00D N00X C00Y 115.6(3) . . ?
N00E C00Y N00X 121.9(3) . . ?
N00E C00Y C014 108.1(3) . . ?
C014 C00Y N00X 130.0(3) . . ?
C011 C00Z N00V 128.3(4) . . ?
C011 C00Z C016 102.6(4) . . ?
C016 C00Z N00V 129.1(4) . . ?
N00K C010 N00Q 119.6(2) . . ?
N00K C010 C014 112.6(3) . . ?
C014 C010 N00Q 127.7(3) . . ?
N005 C011 N00G 122.2(4) . . ?
N005 C011 C00Z 108.2(4) . . ?
C00Z C011 N00G 129.6(4) . . ?
N00F C012 N00S 119.3(3) . . ?
N00F C012 C015 112.9(3) . . ?
C015 C012 N00S 127.8(3) . . ?
N00N C013 N00M 122.1(3) . . ?
N00N C013 C015 107.2(3) . . ?
C015 C013 N00M 130.7(3) . . ?
C00Y C014 N00P 128.6(3) . . ?
C00Y C014 C010 102.9(3) . . ?
C010 C014 N00P 128.5(3) . . ?
C012 C015 N00O 128.9(3) . . ?
C013 C015 N00O 127.5(3) . . ?
C013 C015 C012 103.6(3) . . ?
N008 C016 N00I 121.0(4) . . ?
N008 C016 C00Z 112.3(4) . . ?
C00Z C016 N00I 126.7(4) . . ?

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
O001 N00I C016 N008 179.3(3) . . . . ?
O001 N00I C016 C00Z -1.3(4) . . . . ?
O002 N00Q C010 N00K -172.9(4) . . . . ?
O002 N00Q C010 C014 10.6(6) . . . . ?
O003 N00Q C010 N00K 8.3(5) . . . . ?
O003 N00Q C010 C014 -168.2(4) . . . . ?
O004 N00G C011 N005 176.5(3) . . . . ?
O004 N00G C011 C00Z -4.2(5) . . . . ?
N005 N008 C016 N00I -179.6(3) . . . . ?
N005 N008 C016 C00Z 0.9(3) . . . . ?
O006 N00S C012 N00F 16.6(6) . . . . ?
O006 N00S C012 C015 -163.2(5) . . . . ?
O007 N00X C00Y N00E 8.9(7) . . . . ?
O007 N00X C00Y C014 -171.9(5) . . . . ?
N008 N005 C011 N00G -179.6(3) . . . . ?
N008 N005 C011 C00Z 0.9(3) . . . . ?
O009 N00M C013 N00N 7.6(5) . . . . ?
O009 N00M C013 C015 -171.5(4) . . . . ?
O00A N00S C012 N00F -163.5(4) . . . . ?
O00A N00S C012 C015 16.6(6) . . . . ?
O00B N00M C013 N00N -174.0(4) . . . . ?
O00B N00M C013 C015 6.9(6) . . . . ?
O00C N00O C015 C012 63.9(5) . . . . ?
O00C N00O C015 C013 -116.7(4) . . . . ?
O00D N00X C00Y N00E -171.3(4) . . . . ?
O00D N00X C00Y C014 8.0(7) . . . . ?
N00E N00K C010 N00Q -176.9(3) . . . . ?
N00E N00K C010 C014 0.1(5) . . . . ?
N00E C00Y C014 N00P -179.0(4) . . . . ?
N00E C00Y C014 C010 0.2(5) . . . . ?
N00F N00N C013 N00M -179.0(3) . . . . ?
N00F N00N C013 C015 0.2(4) . . . . ?
N00F C012 C015 N00O 179.4(4) . . . . ?
N00F C012 C015 C013 0.0(5) . . . . ?
O00H N00V C00Z C011 -94.6(4) . . . . ?
O00H N00V C00Z C016 84.9(4) . . . . ?
O00J N00P C014 C00Y -109.9(5) . . . . ?
O00J N00P C014 C010 71.1(5) . . . . ?
N00K N00E C00Y N00X 179.2(4) . . . . ?
N00K N00E C00Y C014 -0.2(5) . . . . ?
N00K C010 C014 N00P 179.0(4) . . . . ?
N00K C010 C014 C00Y -0.2(5) . . . . ?
O00L N00V C00Z C011 85.7(4) . . . . ?
O00L N00V C00Z C016 -94.8(4) . . . . ?
N00M C013 C015 N00O -0.4(7) . . . . ?
N00M C013 C015 C012 179.1(4) . . . . ?
N00N N00F C012 N00S -179.7(3) . . . . ?
N00N N00F C012 C015 0.2(4) . . . . ?
N00N C013 C015 N00O -179.6(4) . . . . ?
N00N C013 C015 C012 -0.1(4) . . . . ?
N00Q C010 C014 N00P -4.3(7) . . . . ?
N00Q C010 C014 C00Y 176.5(4) . . . . ?
O00R N00G C011 N005 -3.2(4) . . . . ?
O00R N00G C011 C00Z 176.1(3) . . . . ?
N00S C012 C015 N00O -0.7(7) . . . . ?
N00S C012 C015 C013 179.8(4) . . . . ?
O00T N00O C015 C012 -115.8(5) . . . . ?
O00T N00O C015 C013 63.5(5) . . . . ?
O00U N00I C016 N008 -1.3(4) . . . . ?
O00U N00I C016 C00Z 178.2(3) . . . . ?
N00V C00Z C011 N005 179.3(3) . . . . ?
N00V C00Z C011 N00G -0.1(5) . . . . ?
N00V C00Z C016 N008 -179.9(3) . . . . ?
N00V C00Z C016 N00I 0.6(5) . . . . ?
O00W N00P C014 C00Y 68.2(6) . . . . ?
O00W N00P C014 C010 -110.8(4) . . . . ?
N00X C00Y C014 N00P 1.7(8) . . . . ?
N00X C00Y C014 C010 -179.1(4) . . . . ?
C00Y N00E N00K C010 0.1(5) . . . . ?
C011 N005 N008 C016 -1.1(3) . . . . ?
C011 C00Z C016 N008 -0.4(3) . . . . ?
C011 C00Z C016 N00I -179.9(3) . . . . ?
C012 N00F N00N C013 -0.2(4) . . . . ?
C016 C00Z C011 N005 -0.3(3) . . . . ?
C016 C00Z C011 N00G -179.7(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_2tnp_p01_model
_audit_block_doi                 10.5517/ccdc.csd.cc29gp0h
_database_code_depnum_ccdc_archive 'CCDC 2129266'
loop_
_audit_author_name
_audit_author_address
'Liu X.'
;The University of Edinburgh
United Kingdom
;
_audit_update_record             
;
2021-12-16 deposited with the CCDC.	2023-11-20 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_THETM01_2tnp_p01_model      
;
PROBLEM: The value of sine(theta_max)/wavelength is less than 0.550
RESPONSE: high pressure data
;
_vrf_PLAT029_2tnp_p01_model      
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.597 Why?
RESPONSE: high pressure data
;
_vrf_PLAT088_2tnp_p01_model      
;
PROBLEM: Poor Data / Parameter Ratio ....................       4.52 Note
RESPONSE: high pressure data
;
_vrf_PLAT110_2tnp_p01_model      
;
PROBLEM: ADDSYM Detects Potential Lattice Translation ...          ? Check
RESPONSE: the nature with this crystal - if the data quality is not good enough to clear locate H atoms, stuture falls into Pseudo sysmetry C2/c ( DOI: 10.1002/anie.201006000)
;
_vrf_PLAT112_2tnp_p01_model      
;
PROBLEM: ADDSYM Detects New (Pseudo) Symm. Elem         I        100 %Fit
RESPONSE: the nature with this crystal - if the data quality is not good enough to clear locate H atoms, stuture falls into Pseudo sysmetry C2/c ( DOI: 10.1002/anie.201006000)
;
_vrf_PLAT113_2tnp_p01_model      
;
PROBLEM: ADDSYM Suggests Possible Pseudo/New  Space Group       I2/a Check
RESPONSE: the nature with this crystal - if the data quality is not good enough to clear locate H atoms, stuture falls into Pseudo sysmetry C2/c ( DOI: 10.1002/anie.201006000)
;
# Added during the CSD deposition process: Thursday 16 December 2021 05:11 PM
# end Validation Reply Form

_audit_creation_date             2021-12-16
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
?
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '3(C6 H2 N10 O12)'
_chemical_formula_sum            'C18 H6 N30 O36'
_chemical_formula_weight         1218.53
_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                   15.1040(12)
_cell_length_b                   8.2460(10)
_cell_length_c                   17.1411(12)
_cell_angle_alpha                90
_cell_angle_beta                 92.235(4)
_cell_angle_gamma                90
_cell_volume                     2133.3(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2353
_cell_measurement_temperature    298.0
_cell_measurement_theta_max      23.00
_cell_measurement_theta_min      2.70
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.185
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6507
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0900 before and 0.0486 after correction.
The Ratio of minimum to maximum transmission is 0.8730.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.897
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1224
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0462
_diffrn_reflns_av_unetI/netI     0.0439
_diffrn_reflns_Laue_measured_fraction_full 0.597
_diffrn_reflns_Laue_measured_fraction_max 0.597
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            10171
_diffrn_reflns_point_group_measured_fraction_full 0.597
_diffrn_reflns_point_group_measured_fraction_max 0.597
_diffrn_reflns_theta_full        22.980
_diffrn_reflns_theta_max         22.980
_diffrn_reflns_theta_min         2.378
_diffrn_ambient_temperature      298.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.597
_diffrn_measured_fraction_theta_max 0.597
_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                1155
_reflns_number_total             1766
_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 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    ?
_refine_diff_density_max         0.133
_refine_diff_density_min         -0.131
_refine_diff_density_rms         0.034
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.100
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     391
_refine_ls_number_reflns         1766
_refine_ls_number_restraints     306
_refine_ls_R_factor_all          0.0783
_refine_ls_R_factor_gt           0.0453
_refine_ls_restrained_S_all      1.017
_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)+(0.0650P)²+0.9840P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1128
_refine_ls_wR_factor_ref         0.1319
_refine_special_details          ?
_olex2_refinement_description    
;
1. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
;
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     ?
_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
O001 O 0.8246(2) 0.5958(6) 0.35549(19) 0.0571(14) Uani 1 1 d . . . . .
O002 O 0.6819(2) 0.6025(6) 0.64829(19) 0.0542(13) Uani 1 1 d . . . . .
O003 O 0.5277(2) 0.4881(5) 0.81246(16) 0.0529(13) Uani 1 1 d . . . . .
O004 O 0.66446(18) 0.4175(5) 0.83326(15) 0.0544(12) Uani 1 1 d . . . . .
O005 O 0.9264(2) 0.1148(6) 0.50972(17) 0.0623(14) Uani 1 1 d . . . . .
O006 O 0.5675(2) 0.1244(6) 0.48678(18) 0.0606(14) Uani 1 1 d . . . . .
O007 O 0.9767(2) 0.4640(5) 0.18054(16) 0.0549(13) Uani 1 1 d . . . . .
N008 N 0.7647(2) 0.9302(6) 0.4657(2) 0.0299(11) Uani 1 1 d . . . . .
O009 O 1.1190(2) 0.3101(6) 0.33961(19) 0.0706(14) Uani 1 1 d . . . . .
N00A N 0.8350(2) 0.2579(5) 0.30115(19) 0.0309(12) Uani 1 1 d . . . . .
O00B O 1.0333(2) 0.2828(5) 0.49177(17) 0.0610(13) Uani 1 1 d . . . . .
O00C O 0.83782(19) 0.4069(5) 0.16181(16) 0.0622(13) Uani 1 1 d . . . . .
O00D O 0.4605(2) 0.2929(5) 0.50449(17) 0.0621(13) Uani 1 1 d . . . . .
N00E N 0.7308(2) 0.9379(5) 0.5364(2) 0.0307(11) Uani 1 1 d . . . . .
O00F O 0.4489(2) 0.5840(7) 0.6580(2) 0.0772(18) Uani 1 1 d . . . . .
N00G N 0.6875(2) 0.7449(7) 0.6323(2) 0.0378(14) Uani 1 1 d . . . . .
O00H O 0.8225(2) 0.4371(6) 0.52268(19) 0.0730(15) Uani 1 1 d . . . . .
N00I N 0.8480(2) 0.2044(5) 0.37456(17) 0.0328(12) Uani 1 1 d . . . . .
O00J O 0.6850(2) 0.4299(6) 0.4872(2) 0.0694(14) Uani 1 1 d . . . . .
N00K N 0.6427(2) 0.2028(6) 0.6279(2) 0.0320(12) Uani 1 1 d . . . . .
N00L N 0.8139(3) 0.7378(7) 0.3697(2) 0.0399(14) Uani 1 1 d . . . . .
N00M N 0.6628(2) 0.2529(5) 0.70025(19) 0.0304(12) Uani 1 1 d . . . . .
N00N N 0.4451(3) 0.4374(8) 0.6587(2) 0.0461(15) Uani 1 1 d . . . . .
N00O N 0.5955(2) 0.4219(5) 0.79400(18) 0.0344(12) Uani 1 1 d . . . . .
N00P N 0.9069(2) 0.4087(5) 0.20016(18) 0.0368(13) Uani 1 1 d . . . . .
O00Q O 0.6655(3) 0.8580(6) 0.67327(19) 0.0732(14) Uani 1 1 d . . . . .
O00R O 0.8302(3) 0.8519(6) 0.32688(19) 0.0741(14) Uani 1 1 d . . . . .
N00S N 0.7528(3) 0.5017(7) 0.50367(19) 0.0402(11) Uani 1 1 d . . . . .
N00T N 0.9654(2) 0.2128(6) 0.4717(2) 0.0430(14) Uani 1 1 d . . . . .
O00U O 0.3788(2) 0.3555(6) 0.65818(19) 0.0735(15) Uani 1 1 d . . . . .
C00V C 0.7225(2) 0.7847(7) 0.5572(2) 0.0280(13) Uani 1 1 d . . . . .
C00W C 0.7778(2) 0.7770(7) 0.4434(2) 0.0275(13) Uani 1 1 d . . . . .
N00X N 0.5279(2) 0.2204(6) 0.5249(2) 0.0418(13) Uani 1 1 d . . . . .
C00Y C 0.5944(2) 0.3434(6) 0.7193(2) 0.0268(13) Uani 1 1 d . . . . .
N00Z N 1.0580(3) 0.4063(7) 0.3351(2) 0.0438(15) Uani 1 1 d . . . . .
C010 C 0.5635(3) 0.2589(6) 0.6023(2) 0.0282(13) Uani 1 1 d . . . . .
C011 C 0.9295(2) 0.2501(6) 0.3940(2) 0.0278(13) Uani 1 1 d . . . . .
O012 O 1.0631(2) 0.5511(7) 0.3311(2) 0.0785(18) Uani 1 1 d . . . . .
C013 C 0.7515(3) 0.6769(7) 0.5017(2) 0.0285(11) Uani 1 1 d . . . . .
C014 C 0.9692(2) 0.3337(6) 0.3355(2) 0.0307(14) Uani 1 1 d . . . . .
C015 C 0.9061(2) 0.3369(6) 0.2765(2) 0.0277(13) Uani 1 1 d . . . . .
C016 C 0.5297(2) 0.3496(6) 0.6596(2) 0.0272(13) Uani 1 1 d . . . . .
H008 H 0.784(3) 1.030(7) 0.433(2) 0.059(15) Uiso 1 1 d . . . . .
H00A H 0.780(3) 0.250(6) 0.273(2) 0.059(14) Uiso 1 1 d . . . . .
H00K H 0.673(4) 0.112(9) 0.602(3) 0.10(2) 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
O001 N00L 1.208(6) . ?
O002 N00G 1.210(6) . ?
O003 N00O 1.213(4) . ?
O004 N00O 1.218(4) . ?
O005 N00T 1.206(5) . ?
O006 N00X 1.201(5) . ?
O007 N00P 1.208(4) . ?
N008 N00E 1.335(5) . ?
N008 C00W 1.337(6) . ?
N008 H008 1.04(5) . ?
O009 N00Z 1.215(6) . ?
N00A N00I 1.341(4) . ?
N00A C015 1.339(5) . ?
N00A H00A 0.94(4) . ?
O00B N00T 1.215(4) . ?
O00C N00P 1.211(4) . ?
O00D N00X 1.219(4) . ?
N00E C00V 1.321(6) . ?
O00F N00N 1.210(6) . ?
N00G O00Q 1.220(6) . ?
N00G C00V 1.449(6) . ?
O00H N00S 1.214(5) . ?
N00I C011 1.318(5) . ?
O00J N00S 1.206(5) . ?
N00K N00M 1.331(5) . ?
N00K C010 1.341(5) . ?
N00K H00K 0.99(6) . ?
N00L O00R 1.224(6) . ?
N00L C00W 1.432(6) . ?
N00M C00Y 1.326(5) . ?
N00N O00U 1.208(6) . ?
N00N C016 1.468(6) . ?
N00O C00Y 1.434(5) . ?
N00P C015 1.436(5) . ?
N00S C013 1.445(7) . ?
N00T C011 1.451(5) . ?
C00V C013 1.385(7) . ?
C00W C013 1.368(7) . ?
N00X C010 1.447(5) . ?
C00Y C016 1.388(5) . ?
N00Z O012 1.198(6) . ?
N00Z C014 1.469(6) . ?
C010 C016 1.351(6) . ?
C011 C014 1.375(6) . ?
C014 C015 1.363(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
N00E N008 C00W 111.8(4) . . ?
N00E N008 H008 125(3) . . ?
C00W N008 H008 123(3) . . ?
N00I N00A H00A 123(2) . . ?
C015 N00A N00I 111.5(3) . . ?
C015 N00A H00A 125(2) . . ?
C00V N00E N008 104.1(4) . . ?
O002 N00G O00Q 126.1(5) . . ?
O002 N00G C00V 116.8(5) . . ?
O00Q N00G C00V 117.1(6) . . ?
C011 N00I N00A 104.1(3) . . ?
N00M N00K C010 111.5(3) . . ?
N00M N00K H00K 124(3) . . ?
C010 N00K H00K 123(3) . . ?
O001 N00L O00R 126.4(5) . . ?
O001 N00L C00W 117.0(5) . . ?
O00R N00L C00W 116.6(6) . . ?
C00Y N00M N00K 104.7(3) . . ?
O00F N00N C016 116.8(4) . . ?
O00U N00N O00F 126.8(5) . . ?
O00U N00N C016 116.4(6) . . ?
O003 N00O O004 125.5(4) . . ?
O003 N00O C00Y 117.1(3) . . ?
O004 N00O C00Y 117.4(3) . . ?
O007 N00P O00C 126.6(4) . . ?
O007 N00P C015 116.6(3) . . ?
O00C N00P C015 116.9(3) . . ?
O00H N00S C013 117.1(4) . . ?
O00J N00S O00H 124.5(6) . . ?
O00J N00S C013 118.3(4) . . ?
O005 N00T O00B 126.2(3) . . ?
O005 N00T C011 117.7(4) . . ?
O00B N00T C011 116.1(4) . . ?
N00E C00V N00G 119.9(5) . . ?
N00E C00V C013 113.1(4) . . ?
C013 C00V N00G 127.0(6) . . ?
N008 C00W N00L 122.1(5) . . ?
N008 C00W C013 108.1(4) . . ?
C013 C00W N00L 129.8(6) . . ?
O006 N00X O00D 126.5(3) . . ?
O006 N00X C010 117.8(4) . . ?
O00D N00X C010 115.6(4) . . ?
N00M C00Y N00O 119.4(3) . . ?
N00M C00Y C016 111.9(4) . . ?
C016 C00Y N00O 128.7(4) . . ?
O009 N00Z C014 115.0(6) . . ?
O012 N00Z O009 127.2(5) . . ?
O012 N00Z C014 117.8(4) . . ?
N00K C010 N00X 121.4(4) . . ?
N00K C010 C016 108.1(3) . . ?
C016 C010 N00X 130.5(4) . . ?
N00I C011 N00T 118.9(4) . . ?
N00I C011 C014 112.9(3) . . ?
C014 C011 N00T 128.2(4) . . ?
C00V C013 N00S 129.0(5) . . ?
C00W C013 N00S 128.0(5) . . ?
C00W C013 C00V 102.9(5) . . ?
C011 C014 N00Z 129.2(3) . . ?
C015 C014 N00Z 127.0(4) . . ?
C015 C014 C011 103.8(3) . . ?
N00A C015 N00P 121.6(3) . . ?
N00A C015 C014 107.6(4) . . ?
C014 C015 N00P 130.8(4) . . ?
C00Y C016 N00N 127.8(4) . . ?
C010 C016 N00N 128.3(3) . . ?
C010 C016 C00Y 103.9(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
O001 N00L C00W N008 178.8(4) . . . . ?
O001 N00L C00W C013 -1.1(6) . . . . ?
O002 N00G C00V N00E -179.6(3) . . . . ?
O002 N00G C00V C013 -0.9(6) . . . . ?
O003 N00O C00Y N00M -171.9(5) . . . . ?
O003 N00O C00Y C016 9.3(8) . . . . ?
O004 N00O C00Y N00M 8.6(7) . . . . ?
O004 N00O C00Y C016 -170.2(5) . . . . ?
O005 N00T C011 N00I 14.3(8) . . . . ?
O005 N00T C011 C014 -167.4(6) . . . . ?
O006 N00X C010 N00K 6.7(9) . . . . ?
O006 N00X C010 C016 -173.5(6) . . . . ?
O007 N00P C015 N00A -173.3(4) . . . . ?
O007 N00P C015 C014 7.6(8) . . . . ?
N008 N00E C00V N00G 179.7(3) . . . . ?
N008 N00E C00V C013 0.8(4) . . . . ?
N008 C00W C013 N00S 179.6(4) . . . . ?
N008 C00W C013 C00V 0.4(4) . . . . ?
O009 N00Z C014 C011 65.6(7) . . . . ?
O009 N00Z C014 C015 -115.5(6) . . . . ?
N00A N00I C011 N00T 179.3(4) . . . . ?
N00A N00I C011 C014 0.8(5) . . . . ?
O00B N00T C011 N00I -166.7(4) . . . . ?
O00B N00T C011 C014 11.5(8) . . . . ?
O00C N00P C015 N00A 6.3(7) . . . . ?
O00C N00P C015 C014 -172.9(5) . . . . ?
O00D N00X C010 N00K -171.8(5) . . . . ?
O00D N00X C010 C016 8.0(9) . . . . ?
N00E N008 C00W N00L -179.9(3) . . . . ?
N00E N008 C00W C013 0.1(4) . . . . ?
N00E C00V C013 N00S -179.9(4) . . . . ?
N00E C00V C013 C00W -0.8(5) . . . . ?
O00F N00N C016 C00Y 67.9(7) . . . . ?
O00F N00N C016 C010 -110.6(6) . . . . ?
N00G C00V C013 N00S 1.3(7) . . . . ?
N00G C00V C013 C00W -179.5(3) . . . . ?
O00H N00S C013 C00V -98.7(5) . . . . ?
O00H N00S C013 C00W 82.3(5) . . . . ?
N00I N00A C015 N00P -178.5(4) . . . . ?
N00I N00A C015 C014 0.9(6) . . . . ?
N00I C011 C014 N00Z 178.8(5) . . . . ?
N00I C011 C014 C015 -0.3(6) . . . . ?
O00J N00S C013 C00V 80.6(6) . . . . ?
O00J N00S C013 C00W -98.3(5) . . . . ?
N00K N00M C00Y N00O -178.1(4) . . . . ?
N00K N00M C00Y C016 0.8(6) . . . . ?
N00K C010 C016 N00N 179.3(5) . . . . ?
N00K C010 C016 C00Y 0.5(6) . . . . ?
N00L C00W C013 N00S -0.5(7) . . . . ?
N00L C00W C013 C00V -179.6(4) . . . . ?
N00M N00K C010 N00X 179.8(5) . . . . ?
N00M N00K C010 C016 0.0(6) . . . . ?
N00M C00Y C016 N00N -179.7(5) . . . . ?
N00M C00Y C016 C010 -0.9(6) . . . . ?
N00O C00Y C016 N00N -0.8(8) . . . . ?
N00O C00Y C016 C010 178.0(5) . . . . ?
O00Q N00G C00V N00E 1.2(6) . . . . ?
O00Q N00G C00V C013 179.9(4) . . . . ?
O00R N00L C00W N008 -1.7(6) . . . . ?
O00R N00L C00W C013 178.3(4) . . . . ?
N00T C011 C014 N00Z 0.5(9) . . . . ?
N00T C011 C014 C015 -178.6(5) . . . . ?
O00U N00N C016 C00Y -112.6(5) . . . . ?
O00U N00N C016 C010 68.9(7) . . . . ?
C00W N008 N00E C00V -0.5(4) . . . . ?
N00X C010 C016 N00N -0.5(10) . . . . ?
N00X C010 C016 C00Y -179.3(5) . . . . ?
N00Z C014 C015 N00A -179.5(5) . . . . ?
N00Z C014 C015 N00P -0.2(9) . . . . ?
C010 N00K N00M C00Y -0.5(6) . . . . ?
C011 C014 C015 N00A -0.4(6) . . . . ?
C011 C014 C015 N00P 178.9(5) . . . . ?
O012 N00Z C014 C011 -113.8(6) . . . . ?
O012 N00Z C014 C015 65.1(7) . . . . ?
C015 N00A N00I C011 -1.0(5) . . . . ?

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

data_2tnp_p05
_audit_block_doi                 10.5517/ccdc.csd.cc29gp4m
_database_code_depnum_ccdc_archive 'CCDC 2129270'
loop_
_audit_author_name
_audit_author_address
'Liu X.'
;The University of Edinburgh
United Kingdom
;
_audit_update_record             
;
2021-12-16 deposited with the CCDC.	2023-11-20 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT029_2tnp_p05            
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.551 Why?
RESPONSE: high pressure data
;
_vrf_PLAT088_2tnp_p05            
;
PROBLEM: Poor Data / Parameter Ratio ....................       5.19 Note
RESPONSE: high pressure data
;
_vrf_PLAT430_2tnp_p05            
;
PROBLEM: Short Inter D...A Contact  O002     ..N00P     .       2.87 Ang.
RESPONSE: high pressure data
;
# Added during the CSD deposition process: Thursday 16 December 2021 05:11 PM
# end Validation Reply Form

_audit_creation_date             2021-12-16
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
?
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '3(C3 H N5 O6)'
_chemical_formula_sum            'C9 H3 N15 O18'
_chemical_formula_weight         609.26
_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                   14.6452(10)
_cell_length_b                   7.9546(7)
_cell_length_c                   16.7946(9)
_cell_angle_alpha                90
_cell_angle_beta                 92.018(4)
_cell_angle_gamma                90
_cell_volume                     1955.3(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2710
_cell_measurement_temperature    298.4
_cell_measurement_theta_max      23.80
_cell_measurement_theta_min      2.78
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.201
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6801
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.070
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1224
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0452
_diffrn_reflns_av_unetI/netI     0.0529
_diffrn_reflns_Laue_measured_fraction_full 0.551
_diffrn_reflns_Laue_measured_fraction_max 0.509
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            10399
_diffrn_reflns_point_group_measured_fraction_full 0.551
_diffrn_reflns_point_group_measured_fraction_max 0.509
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.369
_diffrn_reflns_theta_min         2.427
_diffrn_ambient_temperature      298.4
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.551
_diffrn_measured_fraction_theta_max 0.509
_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                1445
_reflns_number_total             2028
_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 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.186
_refine_diff_density_min         -0.209
_refine_diff_density_rms         0.050
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     391
_refine_ls_number_reflns         2028
_refine_ls_number_restraints     306
_refine_ls_R_factor_all          0.0761
_refine_ls_R_factor_gt           0.0458
_refine_ls_restrained_S_all      0.993
_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)+(0.0822P)²+1.1680P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1243
_refine_ls_wR_factor_ref         0.1430
_refine_special_details          ?
_olex2_refinement_description    
;
1. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
;
_atom_sites_solution_hydrogens   difmap
_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
O001 O 0.5194(2) 0.5008(5) 0.81127(16) 0.0386(9) Uani 1 1 d . . . . .
O002 O 0.6858(2) 0.5934(5) 0.65224(17) 0.0432(10) Uani 1 1 d . . . . .
O003 O 0.65993(19) 0.4232(4) 0.83337(16) 0.0370(9) Uani 1 1 d . . . . .
O004 O 0.9816(2) 0.4519(5) 0.17331(17) 0.0465(10) Uani 1 1 d . . . . .
O005 O 0.8371(2) 0.6013(5) 0.35493(18) 0.0462(10) Uani 1 1 d . . . . .
O006 O 0.5608(2) 0.1300(5) 0.47833(17) 0.0443(10) Uani 1 1 d . . . . .
N007 N 0.7582(2) 0.9386(5) 0.4639(2) 0.0218(9) Uani 1 1 d . . . . .
O008 O 0.4552(2) 0.3151(5) 0.49631(16) 0.0471(10) Uani 1 1 d . . . . .
O009 O 0.9239(2) 0.1032(5) 0.50898(19) 0.0507(11) Uani 1 1 d . . . . .
N00A N 0.7247(2) 0.9423(5) 0.53654(18) 0.0234(8) Uani 1 1 d . . . . .
N00B N 0.6880(2) 0.7419(6) 0.6359(2) 0.0289(9) Uani 1 1 d . . . . .
O00C O 0.6952(2) 0.4125(5) 0.48341(18) 0.0464(9) Uani 1 1 d . . . . .
O00D O 1.1225(2) 0.2837(5) 0.33955(18) 0.0513(11) Uani 1 1 d . . . . .
N00E N 0.6377(2) 0.2042(5) 0.62316(19) 0.0236(9) Uani 1 1 d . . . . .
O00F O 0.8359(2) 0.4061(5) 0.15506(17) 0.0490(10) Uani 1 1 d . . . . .
N00G N 0.8158(2) 0.7450(5) 0.3667(2) 0.0286(10) Uani 1 1 d . . . . .
O00H O 1.0324(2) 0.2831(5) 0.49406(17) 0.0495(10) Uani 1 1 d . . . . .
O00I O 1.0750(2) 0.5390(5) 0.3224(2) 0.0551(12) Uani 1 1 d . . . . .
O00J O 0.8239(2) 0.8627(5) 0.32131(18) 0.0499(10) Uani 1 1 d . . . . .
O00K O 0.8332(2) 0.4355(5) 0.5295(2) 0.0550(11) Uani 1 1 d . . . . .
N00L N 0.8287(2) 0.2629(5) 0.29933(18) 0.0234(9) Uani 1 1 d . . . . .
O00M O 0.4395(2) 0.6015(6) 0.65469(19) 0.0572(12) Uani 1 1 d . . . . .
N00N N 0.8408(2) 0.2102(5) 0.37433(18) 0.0242(9) Uani 1 1 d . . . . .
N00O N 0.4360(2) 0.4501(6) 0.65527(19) 0.0318(10) Uani 1 1 d . . . . .
N00P N 0.6581(2) 0.2511(5) 0.69858(18) 0.0251(9) Uani 1 1 d . . . . .
N00Q N 0.5890(2) 0.4290(5) 0.79323(18) 0.0247(9) Uani 1 1 d . . . . .
O00R O 0.6644(3) 0.8557(6) 0.67854(19) 0.0586(12) Uani 1 1 d . . . . .
O00S O 0.3679(2) 0.3643(5) 0.65521(19) 0.0583(11) Uani 1 1 d . . . . .
N00T N 1.0622(2) 0.3906(6) 0.33102(19) 0.0317(10) Uani 1 1 d . . . . .
N00U N 0.9638(2) 0.2075(5) 0.47170(19) 0.0300(10) Uani 1 1 d . . . . .
N00V N 0.5220(2) 0.2330(5) 0.5177(2) 0.0295(9) Uani 1 1 d . . . . .
N00W N 0.7613(2) 0.4935(5) 0.50531(17) 0.0294(9) Uani 1 1 d . . . . .
N00X N 0.9075(2) 0.4021(5) 0.19409(19) 0.0311(10) Uani 1 1 d . . . . .
C00Y C 0.7218(3) 0.7851(6) 0.5592(2) 0.0211(10) Uani 1 1 d . . . . .
C00Z C 0.7778(3) 0.7821(6) 0.4420(2) 0.0204(10) Uani 1 1 d . . . . .
C010 C 0.5872(2) 0.3467(5) 0.7173(2) 0.0190(9) Uani 1 1 d . . . . .
C011 C 0.5581(3) 0.2673(6) 0.5968(2) 0.0226(10) Uani 1 1 d . . . . .
C012 C 0.9269(3) 0.2500(6) 0.3934(2) 0.0221(10) Uani 1 1 d . . . . .
C013 C 0.5223(2) 0.3603(5) 0.6564(2) 0.0213(10) Uani 1 1 d . . . . .
C014 C 0.9702(2) 0.3296(6) 0.3322(2) 0.0228(10) Uani 1 1 d . . . . .
C015 C 0.9044(3) 0.3347(6) 0.2724(2) 0.0239(10) Uani 1 1 d . . . . .
C016 C 0.7543(2) 0.6743(6) 0.5025(2) 0.0226(10) Uani 1 1 d . . . . .
H00E H 0.673(3) 0.128(6) 0.598(2) 0.031(12) Uiso 1 1 d . . . . .
H00L H 0.769(4) 0.274(8) 0.273(3) 0.10(2) Uiso 1 1 d . . . . .
H007 H 0.776(3) 1.040(8) 0.432(3) 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
O001 N00Q 1.216(4) . ?
O002 N00B 1.213(5) . ?
O003 N00Q 1.219(4) . ?
O004 N00X 1.218(4) . ?
O005 N00G 1.203(5) . ?
O006 N00V 1.208(4) . ?
N007 N00A 1.331(5) . ?
N007 C00Z 1.333(6) . ?
N007 H007 1.01(5) . ?
O008 N00V 1.219(4) . ?
O009 N00U 1.203(5) . ?
N00A C00Y 1.308(6) . ?
N00B O00R 1.212(5) . ?
N00B C00Y 1.439(6) . ?
O00C N00W 1.209(5) . ?
O00D N00T 1.231(5) . ?
N00E N00P 1.344(4) . ?
N00E C011 1.331(5) . ?
N00E H00E 0.91(4) . ?
O00F N00X 1.217(4) . ?
N00G O00J 1.216(5) . ?
N00G C00Z 1.430(5) . ?
O00H N00U 1.218(4) . ?
O00I N00T 1.205(5) . ?
O00K N00W 1.207(4) . ?
N00L N00N 1.333(4) . ?
N00L C015 1.340(5) . ?
N00L H00L 0.97(5) . ?
O00M N00O 1.205(5) . ?
N00N C012 1.329(5) . ?
N00O O00S 1.209(5) . ?
N00O C013 1.451(5) . ?
N00P C010 1.333(5) . ?
N00Q C010 1.433(5) . ?
N00T C014 1.433(5) . ?
N00U C012 1.444(5) . ?
N00V C011 1.439(5) . ?
N00W C016 1.442(6) . ?
N00X C015 1.423(5) . ?
C00Y C016 1.394(6) . ?
C00Z C016 1.383(6) . ?
C010 C013 1.377(5) . ?
C011 C013 1.363(5) . ?
C012 C014 1.380(5) . ?
C014 C015 1.367(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
N00A N007 C00Z 111.3(3) . . ?
N00A N007 H007 125(3) . . ?
C00Z N007 H007 123(4) . . ?
C00Y N00A N007 105.2(3) . . ?
O002 N00B C00Y 116.6(4) . . ?
O00R N00B O002 125.7(5) . . ?
O00R N00B C00Y 117.7(5) . . ?
N00P N00E H00E 121(2) . . ?
C011 N00E N00P 111.8(3) . . ?
C011 N00E H00E 127(2) . . ?
O005 N00G O00J 126.7(5) . . ?
O005 N00G C00Z 116.9(4) . . ?
O00J N00G C00Z 116.4(4) . . ?
N00N N00L C015 111.6(3) . . ?
N00N N00L H00L 124(3) . . ?
C015 N00L H00L 123(3) . . ?
C012 N00N N00L 104.2(3) . . ?
O00M N00O O00S 126.8(4) . . ?
O00M N00O C013 117.1(4) . . ?
O00S N00O C013 116.1(5) . . ?
C010 N00P N00E 103.4(3) . . ?
O001 N00Q O003 125.8(3) . . ?
O001 N00Q C010 116.5(3) . . ?
O003 N00Q C010 117.6(3) . . ?
O00D N00T C014 115.8(4) . . ?
O00I N00T O00D 125.3(4) . . ?
O00I N00T C014 118.9(4) . . ?
O009 N00U O00H 126.2(3) . . ?
O009 N00U C012 117.5(4) . . ?
O00H N00U C012 116.3(3) . . ?
O006 N00V O008 126.2(3) . . ?
O006 N00V C011 118.0(4) . . ?
O008 N00V C011 115.8(3) . . ?
O00C N00W C016 117.8(4) . . ?
O00K N00W O00C 125.4(5) . . ?
O00K N00W C016 116.8(4) . . ?
O004 N00X C015 116.4(3) . . ?
O00F N00X O004 126.6(3) . . ?
O00F N00X C015 117.0(3) . . ?
N00A C00Y N00B 120.3(4) . . ?
N00A C00Y C016 113.0(4) . . ?
C016 C00Y N00B 126.7(5) . . ?
N007 C00Z N00G 122.1(4) . . ?
N007 C00Z C016 108.3(4) . . ?
C016 C00Z N00G 129.6(4) . . ?
N00P C010 N00Q 118.7(3) . . ?
N00P C010 C013 113.1(3) . . ?
C013 C010 N00Q 128.1(4) . . ?
N00E C011 N00V 121.6(4) . . ?
N00E C011 C013 108.4(3) . . ?
C013 C011 N00V 130.0(4) . . ?
N00N C012 N00U 119.0(3) . . ?
N00N C012 C014 112.8(3) . . ?
C014 C012 N00U 128.2(3) . . ?
C010 C013 N00O 128.8(4) . . ?
C011 C013 N00O 127.9(3) . . ?
C011 C013 C010 103.3(3) . . ?
C012 C014 N00T 128.5(3) . . ?
C015 C014 N00T 128.2(4) . . ?
C015 C014 C012 103.3(3) . . ?
N00L C015 N00X 121.7(3) . . ?
N00L C015 C014 108.1(3) . . ?
C014 C015 N00X 130.2(4) . . ?
C00Y C016 N00W 129.3(4) . . ?
C00Z C016 N00W 128.6(4) . . ?
C00Z C016 C00Y 102.1(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
O001 N00Q C010 N00P -172.7(4) . . . . ?
O001 N00Q C010 C013 11.5(7) . . . . ?
O002 N00B C00Y N00A 178.7(3) . . . . ?
O002 N00B C00Y C016 -1.6(6) . . . . ?
O003 N00Q C010 N00P 8.2(6) . . . . ?
O003 N00Q C010 C013 -167.5(4) . . . . ?
O004 N00X C015 N00L -174.1(4) . . . . ?
O004 N00X C015 C014 6.6(7) . . . . ?
O005 N00G C00Z N007 174.8(4) . . . . ?
O005 N00G C00Z C016 -6.0(6) . . . . ?
O006 N00V C011 N00E 8.1(8) . . . . ?
O006 N00V C011 C013 -171.1(5) . . . . ?
N007 N00A C00Y N00B -179.6(3) . . . . ?
N007 N00A C00Y C016 0.7(4) . . . . ?
N007 C00Z C016 N00W 178.7(3) . . . . ?
N007 C00Z C016 C00Y -0.8(4) . . . . ?
O008 N00V C011 N00E -170.4(5) . . . . ?
O008 N00V C011 C013 10.3(8) . . . . ?
O009 N00U C012 N00N 18.0(7) . . . . ?
O009 N00U C012 C014 -161.9(5) . . . . ?
N00A N007 C00Z N00G -179.3(3) . . . . ?
N00A N007 C00Z C016 1.3(4) . . . . ?
N00A C00Y C016 N00W -179.5(3) . . . . ?
N00A C00Y C016 C00Z 0.1(4) . . . . ?
N00B C00Y C016 N00W 0.8(6) . . . . ?
N00B C00Y C016 C00Z -179.6(4) . . . . ?
O00C N00W C016 C00Y 86.6(5) . . . . ?
O00C N00W C016 C00Z -92.8(5) . . . . ?
O00D N00T C014 C012 62.2(6) . . . . ?
O00D N00T C014 C015 -117.0(5) . . . . ?
N00E N00P C010 N00Q -175.8(4) . . . . ?
N00E N00P C010 C013 0.6(5) . . . . ?
N00E C011 C013 N00O -178.9(4) . . . . ?
N00E C011 C013 C010 0.6(5) . . . . ?
O00F N00X C015 N00L 6.7(6) . . . . ?
O00F N00X C015 C014 -172.5(5) . . . . ?
N00G C00Z C016 N00W -0.6(7) . . . . ?
N00G C00Z C016 C00Y 179.9(4) . . . . ?
O00H N00U C012 N00N -161.2(4) . . . . ?
O00H N00U C012 C014 19.0(7) . . . . ?
O00I N00T C014 C012 -117.5(5) . . . . ?
O00I N00T C014 C015 63.3(6) . . . . ?
O00J N00G C00Z N007 -4.6(5) . . . . ?
O00J N00G C00Z C016 174.7(4) . . . . ?
O00K N00W C016 C00Y -93.3(5) . . . . ?
O00K N00W C016 C00Z 87.2(5) . . . . ?
N00L N00N C012 N00U -179.0(4) . . . . ?
N00L N00N C012 C014 0.9(5) . . . . ?
O00M N00O C013 C010 70.7(6) . . . . ?
O00M N00O C013 C011 -109.9(5) . . . . ?
N00N N00L C015 N00X -179.3(4) . . . . ?
N00N N00L C015 C014 0.1(5) . . . . ?
N00N C012 C014 N00T 179.8(4) . . . . ?
N00N C012 C014 C015 -0.8(5) . . . . ?
N00P N00E C011 N00V -179.7(4) . . . . ?
N00P N00E C011 C013 -0.2(6) . . . . ?
N00P C010 C013 N00O 178.7(4) . . . . ?
N00P C010 C013 C011 -0.8(5) . . . . ?
N00Q C010 C013 N00O -5.3(8) . . . . ?
N00Q C010 C013 C011 175.2(4) . . . . ?
O00R N00B C00Y N00A -1.4(5) . . . . ?
O00R N00B C00Y C016 178.2(4) . . . . ?
O00S N00O C013 C010 -109.1(5) . . . . ?
O00S N00O C013 C011 70.3(6) . . . . ?
N00T C014 C015 N00L 179.8(4) . . . . ?
N00T C014 C015 N00X -0.9(8) . . . . ?
N00U C012 C014 N00T -0.3(8) . . . . ?
N00U C012 C014 C015 179.1(4) . . . . ?
N00V C011 C013 N00O 0.4(8) . . . . ?
N00V C011 C013 C010 179.9(4) . . . . ?
C00Z N007 N00A C00Y -1.2(4) . . . . ?
C011 N00E N00P C010 -0.2(5) . . . . ?
C012 C014 C015 N00L 0.4(5) . . . . ?
C012 C014 C015 N00X 179.7(4) . . . . ?
C015 N00L N00N C012 -0.6(5) . . . . ?

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

data_2tnp_p02
_audit_block_doi                 10.5517/ccdc.csd.cc29gp5n
_database_code_depnum_ccdc_archive 'CCDC 2129271'
loop_
_audit_author_name
_audit_author_address
'Liu X.'
;The University of Edinburgh
United Kingdom
;
_audit_update_record             
;
2021-12-16 deposited with the CCDC.	2023-11-20 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT029_2tnp_p02            
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.553 Why?
RESPONSE: high pressure data
;
_vrf_PLAT088_2tnp_p02            
;
PROBLEM: Poor Data / Parameter Ratio ....................       5.48 Note
RESPONSE: high pressure data
;
_vrf_PLAT110_2tnp_p02            
;
PROBLEM: ADDSYM Detects Potential Lattice Translation ...          ? Check
RESPONSE: the nature with this crystal - if the data quality is not good enough to clear locate H atoms, stuture falls into Pseudo sysmetry C2/c ( DOI: 10.1002/anie.201006000)
;
_vrf_PLAT112_2tnp_p02            
;
PROBLEM: ADDSYM Detects New (Pseudo) Symm. Elem         I        100 %Fit
RESPONSE: the nature with this crystal - if the data quality is not good enough to clear locate H atoms, stuture falls into Pseudo sysmetry C2/c ( DOI: 10.1002/anie.201006000)
;
_vrf_PLAT113_2tnp_p02            
;
PROBLEM: ADDSYM Suggests Possible Pseudo/New  Space Group       I2/a Check
RESPONSE: the nature with this crystal - if the data quality is not good enough to clear locate H atoms, stuture falls into Pseudo sysmetry C2/c ( DOI: 10.1002/anie.201006000)
;
# Added during the CSD deposition process: Thursday 16 December 2021 05:11 PM
# end Validation Reply Form

_audit_creation_date             2021-12-16
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
?
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '3(C6 H2 N10 O12)'
_chemical_formula_sum            'C18 H6 N30 O36'
_chemical_formula_weight         1218.53
_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                   14.9370(17)
_cell_length_b                   8.1341(11)
_cell_length_c                   16.9890(17)
_cell_angle_alpha                90
_cell_angle_beta                 92.170(7)
_cell_angle_gamma                90
_cell_volume                     2062.7(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2256
_cell_measurement_temperature    298.0
_cell_measurement_theta_max      24.74
_cell_measurement_theta_min      2.73
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.191
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6538
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0839 before and 0.0558 after correction.
The Ratio of minimum to maximum transmission is 0.8771.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.962
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1224
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0563
_diffrn_reflns_av_unetI/netI     0.0651
_diffrn_reflns_Laue_measured_fraction_full 0.553
_diffrn_reflns_Laue_measured_fraction_max 0.507
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            11940
_diffrn_reflns_point_group_measured_fraction_full 0.553
_diffrn_reflns_point_group_measured_fraction_max 0.507
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.380
_diffrn_reflns_theta_min         2.399
_diffrn_ambient_temperature      298.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.553
_diffrn_measured_fraction_theta_max 0.507
_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                1313
_reflns_number_total             2144
_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 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.181
_refine_diff_density_min         -0.192
_refine_diff_density_rms         0.046
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     391
_refine_ls_number_reflns         2144
_refine_ls_number_restraints     306
_refine_ls_R_factor_all          0.0998
_refine_ls_R_factor_gt           0.0512
_refine_ls_restrained_S_all      0.981
_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)+(0.0568P)²+2.7225P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1246
_refine_ls_wR_factor_ref         0.1499
_refine_special_details          ?
_olex2_refinement_description    
;
1. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
;
_atom_sites_solution_hydrogens   difmap
_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
O001 O 0.8274(3) 0.5972(5) 0.3545(2) 0.0527(12) Uani 1 1 d . . . . .
O002 O 0.6821(2) 0.5995(5) 0.6493(2) 0.0500(11) Uani 1 1 d . . . . .
O003 O 0.5252(2) 0.4925(5) 0.8125(2) 0.0459(11) Uani 1 1 d . . . . .
O004 O 0.6631(2) 0.4196(5) 0.83367(19) 0.0458(10) Uani 1 1 d . . . . .
O005 O 0.9260(3) 0.1118(6) 0.5109(2) 0.0562(13) Uani 1 1 d . . . . .
O006 O 0.5655(3) 0.1251(6) 0.4839(2) 0.0534(12) Uani 1 1 d . . . . .
O007 O 0.9783(2) 0.4634(5) 0.1786(2) 0.0510(12) Uani 1 1 d . . . . .
N008 N 0.7625(3) 0.9332(6) 0.4651(3) 0.0268(10) Uani 1 1 d . . . . .
O009 O 1.1209(2) 0.3041(6) 0.3403(2) 0.0627(13) Uani 1 1 d . . . . .
N00A N 0.8338(3) 0.2590(5) 0.3010(2) 0.0274(10) Uani 1 1 d . . . . .
O00B O 1.0332(2) 0.2853(5) 0.4934(2) 0.0560(12) Uani 1 1 d . . . . .
O00C O 0.8367(2) 0.4091(5) 0.1599(2) 0.0546(12) Uani 1 1 d . . . . .
O00D O 0.4586(2) 0.3007(5) 0.5014(2) 0.0559(12) Uani 1 1 d . . . . .
N00E N 0.7291(3) 0.9407(5) 0.5363(2) 0.0278(10) Uani 1 1 d . . . . .
O00F O 0.4461(3) 0.5901(6) 0.6565(2) 0.0681(15) Uani 1 1 d . . . . .
N00G N 0.6874(3) 0.7448(7) 0.6332(3) 0.0328(11) Uani 1 1 d . . . . .
O00H O 0.8256(3) 0.4347(5) 0.5245(2) 0.0627(13) Uani 1 1 d . . . . .
N00I N 0.8460(2) 0.2058(5) 0.3750(2) 0.0283(10) Uani 1 1 d . . . . .
O00J O 0.6876(3) 0.4252(5) 0.4853(2) 0.0599(12) Uani 1 1 d . . . . .
N00K N 0.6410(3) 0.2023(6) 0.6270(3) 0.0302(11) Uani 1 1 d . . . . .
N00L N 0.8140(3) 0.7417(6) 0.3681(3) 0.0347(11) Uani 1 1 d . . . . .
N00M N 0.6618(2) 0.2525(5) 0.6997(2) 0.0282(10) Uani 1 1 d . . . . .
N00N N 0.4425(3) 0.4416(7) 0.6577(2) 0.0399(12) Uani 1 1 d . . . . .
N00O N 0.5940(3) 0.4236(5) 0.7943(2) 0.0313(11) Uani 1 1 d . . . . .
N00P N 0.9071(3) 0.4089(5) 0.1987(2) 0.0334(11) Uani 1 1 d . . . . .
O00Q O 0.6653(3) 0.8565(6) 0.6756(2) 0.0670(14) Uani 1 1 d . . . . .
O00R O 0.8287(3) 0.8560(6) 0.3246(2) 0.0638(13) Uani 1 1 d . . . . .
N00S N 0.7554(3) 0.4981(6) 0.5033(2) 0.0352(10) Uani 1 1 d . . . . .
N00T N 0.9657(3) 0.2125(6) 0.4725(2) 0.0356(11) Uani 1 1 d . . . . .
O00U O 0.3750(3) 0.3581(6) 0.6573(2) 0.0660(13) Uani 1 1 d . . . . .
C00V C 0.7218(3) 0.7850(6) 0.5584(3) 0.0240(11) Uani 1 1 d . . . . .
C00W C 0.7779(3) 0.7783(7) 0.4427(3) 0.0260(12) Uani 1 1 d . . . . .
N00X N 0.5263(3) 0.2251(6) 0.5222(2) 0.0352(11) Uani 1 1 d . . . . .
C00Y C 0.5919(3) 0.3438(6) 0.7187(3) 0.0235(11) Uani 1 1 d . . . . .
N00Z N 1.0593(3) 0.4028(7) 0.3345(2) 0.0394(12) Uani 1 1 d . . . . .
C010 C 0.5620(3) 0.2605(6) 0.5997(3) 0.0270(12) Uani 1 1 d . . . . .
C011 C 0.9290(3) 0.2518(6) 0.3943(3) 0.0262(12) Uani 1 1 d . . . . .
O012 O 1.0671(3) 0.5492(6) 0.3291(2) 0.0714(16) Uani 1 1 d . . . . .
C013 C 0.7519(3) 0.6757(6) 0.5021(3) 0.0256(10) Uani 1 1 d . . . . .
C014 C 0.9699(3) 0.3349(6) 0.3351(3) 0.0252(12) Uani 1 1 d . . . . .
C015 C 0.9056(3) 0.3378(6) 0.2753(3) 0.0276(12) Uani 1 1 d . . . . .
C016 C 0.5271(3) 0.3531(6) 0.6586(3) 0.0257(12) Uani 1 1 d . . . . .
H008 H 0.783(4) 1.028(9) 0.432(4) 0.09(2) Uiso 1 1 d . . . . .
H00K H 0.673(3) 0.138(6) 0.601(2) 0.004(11) Uiso 1 1 d . . . . .
H00A H 0.780(4) 0.254(7) 0.274(3) 0.070(18) 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
O001 N00L 1.216(6) . ?
O002 N00G 1.217(6) . ?
O003 N00O 1.220(5) . ?
O004 N00O 1.209(4) . ?
O005 N00T 1.216(5) . ?
O006 N00X 1.207(5) . ?
O007 N00P 1.213(5) . ?
N008 N00E 1.327(6) . ?
N008 C00W 1.339(7) . ?
N008 H008 1.01(7) . ?
O009 N00Z 1.223(6) . ?
N00A N00I 1.335(5) . ?
N00A C015 1.336(6) . ?
N00A H00A 0.91(5) . ?
O00B N00T 1.211(5) . ?
O00C N00P 1.219(4) . ?
O00D N00X 1.224(5) . ?
N00E C00V 1.327(6) . ?
O00F N00N 1.210(6) . ?
N00G O00Q 1.213(6) . ?
N00G C00V 1.426(7) . ?
O00H N00S 1.211(5) . ?
N00I C011 1.325(5) . ?
O00J N00S 1.203(5) . ?
N00K N00M 1.327(5) . ?
N00K C010 1.338(5) . ?
N00K H00K 0.84(4) . ?
N00L O00R 1.213(6) . ?
N00L C00W 1.427(7) . ?
N00M C00Y 1.330(6) . ?
N00N O00U 1.215(6) . ?
N00N C016 1.454(6) . ?
N00O C00Y 1.439(6) . ?
N00P C015 1.425(6) . ?
N00S C013 1.446(7) . ?
N00T C011 1.453(5) . ?
C00V C013 1.393(7) . ?
C00W C013 1.376(7) . ?
N00X C010 1.430(5) . ?
C00Y C016 1.382(5) . ?
N00Z O012 1.200(6) . ?
N00Z C014 1.446(6) . ?
C010 C016 1.371(7) . ?
C011 C014 1.374(6) . ?
C014 C015 1.371(6) . ?

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
N00E N008 C00W 112.1(4) . . ?
N00E N008 H008 127(5) . . ?
C00W N008 H008 120(5) . . ?
N00I N00A C015 112.4(4) . . ?
N00I N00A H00A 123(3) . . ?
C015 N00A H00A 124(3) . . ?
C00V N00E N008 104.6(4) . . ?
O002 N00G C00V 116.9(4) . . ?
O00Q N00G O002 124.9(6) . . ?
O00Q N00G C00V 118.2(6) . . ?
C011 N00I N00A 103.6(4) . . ?
N00M N00K C010 112.7(4) . . ?
N00M N00K H00K 124(2) . . ?
C010 N00K H00K 123(2) . . ?
O001 N00L C00W 116.2(4) . . ?
O00R N00L O001 126.2(6) . . ?
O00R N00L C00W 117.7(5) . . ?
N00K N00M C00Y 103.8(3) . . ?
O00F N00N O00U 126.6(5) . . ?
O00F N00N C016 117.1(5) . . ?
O00U N00N C016 116.4(5) . . ?
O003 N00O C00Y 116.3(3) . . ?
O004 N00O O003 125.6(4) . . ?
O004 N00O C00Y 118.1(4) . . ?
O007 N00P O00C 126.5(4) . . ?
O007 N00P C015 116.7(4) . . ?
O00C N00P C015 116.8(4) . . ?
O00H N00S C013 117.4(4) . . ?
O00J N00S O00H 125.2(5) . . ?
O00J N00S C013 117.3(4) . . ?
O005 N00T C011 117.7(4) . . ?
O00B N00T O005 126.1(4) . . ?
O00B N00T C011 116.2(4) . . ?
N00E C00V N00G 120.5(5) . . ?
N00E C00V C013 112.5(5) . . ?
C013 C00V N00G 127.0(5) . . ?
N008 C00W N00L 121.6(5) . . ?
N008 C00W C013 107.8(5) . . ?
C013 C00W N00L 130.6(5) . . ?
O006 N00X O00D 126.5(4) . . ?
O006 N00X C010 117.4(4) . . ?
O00D N00X C010 116.1(4) . . ?
N00M C00Y N00O 118.5(4) . . ?
N00M C00Y C016 112.7(4) . . ?
C016 C00Y N00O 128.7(4) . . ?
O009 N00Z C014 116.2(5) . . ?
O012 N00Z O009 125.7(5) . . ?
O012 N00Z C014 118.2(5) . . ?
N00K C010 N00X 122.8(4) . . ?
N00K C010 C016 107.2(4) . . ?
C016 C010 N00X 130.0(4) . . ?
N00I C011 N00T 118.8(4) . . ?
N00I C011 C014 113.2(4) . . ?
C014 C011 N00T 128.0(4) . . ?
C00V C013 N00S 129.8(5) . . ?
C00W C013 N00S 127.3(5) . . ?
C00W C013 C00V 103.0(5) . . ?
C011 C014 N00Z 128.9(4) . . ?
C015 C014 N00Z 127.6(4) . . ?
C015 C014 C011 103.5(4) . . ?
N00A C015 N00P 122.2(4) . . ?
N00A C015 C014 107.3(4) . . ?
C014 C015 N00P 130.4(4) . . ?
C00Y C016 N00N 128.2(4) . . ?
C010 C016 N00N 128.2(4) . . ?
C010 C016 C00Y 103.5(4) . . ?

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
O001 N00L C00W N008 178.3(4) . . . . ?
O001 N00L C00W C013 -2.8(7) . . . . ?
O002 N00G C00V N00E 179.5(4) . . . . ?
O002 N00G C00V C013 -1.4(6) . . . . ?
O003 N00O C00Y N00M -173.0(5) . . . . ?
O003 N00O C00Y C016 10.0(9) . . . . ?
O004 N00O C00Y N00M 8.3(8) . . . . ?
O004 N00O C00Y C016 -168.7(5) . . . . ?
O005 N00T C011 N00I 14.4(9) . . . . ?
O005 N00T C011 C014 -166.2(6) . . . . ?
O006 N00X C010 N00K 7.7(10) . . . . ?
O006 N00X C010 C016 -172.1(7) . . . . ?
O007 N00P C015 N00A -173.0(5) . . . . ?
O007 N00P C015 C014 7.7(9) . . . . ?
N008 N00E C00V N00G -179.8(4) . . . . ?
N008 N00E C00V C013 1.0(5) . . . . ?
N008 C00W C013 N00S 179.4(4) . . . . ?
N008 C00W C013 C00V -0.4(5) . . . . ?
O009 N00Z C014 C011 64.0(8) . . . . ?
O009 N00Z C014 C015 -115.5(6) . . . . ?
N00A N00I C011 N00T -179.7(5) . . . . ?
N00A N00I C011 C014 0.8(6) . . . . ?
O00B N00T C011 N00I -165.0(5) . . . . ?
O00B N00T C011 C014 14.4(9) . . . . ?
O00C N00P C015 N00A 7.1(8) . . . . ?
O00C N00P C015 C014 -172.2(5) . . . . ?
O00D N00X C010 N00K -172.0(5) . . . . ?
O00D N00X C010 C016 8.2(10) . . . . ?
N00E N008 C00W N00L -179.9(4) . . . . ?
N00E N008 C00W C013 1.0(5) . . . . ?
N00E C00V C013 N00S 179.9(4) . . . . ?
N00E C00V C013 C00W -0.4(5) . . . . ?
O00F N00N C016 C00Y 69.4(7) . . . . ?
O00F N00N C016 C010 -109.8(7) . . . . ?
N00G C00V C013 N00S 0.8(8) . . . . ?
N00G C00V C013 C00W -179.5(4) . . . . ?
O00H N00S C013 C00V -96.0(6) . . . . ?
O00H N00S C013 C00W 84.4(6) . . . . ?
N00I N00A C015 N00P -178.5(4) . . . . ?
N00I N00A C015 C014 1.0(6) . . . . ?
N00I C011 C014 N00Z -179.8(5) . . . . ?
N00I C011 C014 C015 -0.2(6) . . . . ?
O00J N00S C013 C00V 82.1(6) . . . . ?
O00J N00S C013 C00W -97.5(6) . . . . ?
N00K N00M C00Y N00O -177.9(5) . . . . ?
N00K N00M C00Y C016 -0.4(7) . . . . ?
N00K C010 C016 N00N -179.8(5) . . . . ?
N00K C010 C016 C00Y 0.9(7) . . . . ?
N00L C00W C013 N00S 0.3(8) . . . . ?
N00L C00W C013 C00V -179.4(4) . . . . ?
N00M N00K C010 N00X 179.0(5) . . . . ?
N00M N00K C010 C016 -1.2(7) . . . . ?
N00M C00Y C016 N00N -179.7(5) . . . . ?
N00M C00Y C016 C010 -0.3(7) . . . . ?
N00O C00Y C016 N00N -2.5(10) . . . . ?
N00O C00Y C016 C010 176.9(5) . . . . ?
O00Q N00G C00V N00E -0.1(6) . . . . ?
O00Q N00G C00V C013 179.0(5) . . . . ?
O00R N00L C00W N008 -1.5(6) . . . . ?
O00R N00L C00W C013 177.4(5) . . . . ?
N00T C011 C014 N00Z 0.7(10) . . . . ?
N00T C011 C014 C015 -179.6(5) . . . . ?
O00U N00N C016 C00Y -111.3(6) . . . . ?
O00U N00N C016 C010 69.4(8) . . . . ?
C00W N008 N00E C00V -1.2(4) . . . . ?
N00X C010 C016 N00N 0.0(11) . . . . ?
N00X C010 C016 C00Y -179.3(5) . . . . ?
N00Z C014 C015 N00A 179.2(5) . . . . ?
N00Z C014 C015 N00P -1.4(10) . . . . ?
C010 N00K N00M C00Y 1.0(7) . . . . ?
C011 C014 C015 N00A -0.4(6) . . . . ?
C011 C014 C015 N00P 178.9(5) . . . . ?
O012 N00Z C014 C011 -115.4(6) . . . . ?
O012 N00Z C014 C015 65.1(7) . . . . ?
C015 N00A N00I C011 -1.1(6) . . . . ?

_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_2tnp_p06
_audit_block_doi                 10.5517/ccdc.csd.cc29gp9s
_database_code_depnum_ccdc_archive 'CCDC 2129275'
loop_
_audit_author_name
_audit_author_address
'Liu X.'
;The University of Edinburgh
United Kingdom
;
_audit_update_record             
;
2021-12-16 deposited with the CCDC.	2023-11-20 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT029_2tnp_p06            
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.551 Why?
RESPONSE: high pressure data
;
_vrf_PLAT088_2tnp_p06            
;
PROBLEM: Poor Data / Parameter Ratio ....................       5.01 Note
RESPONSE: high pressure data
;
# Added during the CSD deposition process: Thursday 16 December 2021 05:11 PM
# end Validation Reply Form

_audit_creation_date             2021-12-16
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
?
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '3(C3 H N5 O6)'
_chemical_formula_sum            'C9 H3 N15 O18'
_chemical_formula_weight         609.26
_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                   14.4526(11)
_cell_length_b                   7.8178(8)
_cell_length_c                   16.7135(11)
_cell_angle_alpha                90
_cell_angle_beta                 92.015(4)
_cell_angle_gamma                90
_cell_volume                     1887.2(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3735
_cell_measurement_temperature    298.4
_cell_measurement_theta_max      24.81
_cell_measurement_theta_min      2.82
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.209
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6775
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0779 before and 0.0528 after correction.
The Ratio of minimum to maximum transmission is 0.9089.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.144
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1224
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0443
_diffrn_reflns_av_unetI/netI     0.0419
_diffrn_reflns_Laue_measured_fraction_full 0.551
_diffrn_reflns_Laue_measured_fraction_max 0.509
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            10757
_diffrn_reflns_point_group_measured_fraction_full 0.551
_diffrn_reflns_point_group_measured_fraction_max 0.509
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.348
_diffrn_reflns_theta_min         2.439
_diffrn_ambient_temperature      298.4
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.551
_diffrn_measured_fraction_theta_max 0.509
_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                1511
_reflns_number_total             1960
_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 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.189
_refine_diff_density_min         -0.178
_refine_diff_density_rms         0.047
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     391
_refine_ls_number_reflns         1960
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0606
_refine_ls_R_factor_gt           0.0402
_refine_ls_restrained_S_all      1.078
_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)+(0.0516P)²+1.7307P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0984
_refine_ls_wR_factor_ref         0.1086
_refine_special_details          ?
_olex2_refinement_description    
;
;
_atom_sites_solution_hydrogens   difmap
_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
O001 O 0.65654(15) 0.5691(4) 0.83147(14) 0.0327(8) Uani 1 1 d . . . . .
O002 O 0.68988(19) 0.4111(5) 0.65493(16) 0.0401(10) Uani 1 1 d . . . . .
O003 O 0.98345(17) 0.5682(4) 0.16702(15) 0.0406(9) Uani 1 1 d . . . . .
O004 O 0.45180(17) 0.6738(4) 0.49229(14) 0.0378(9) Uani 1 1 d . . . . .
O005 O 1.12226(17) 0.7392(4) 0.33606(16) 0.0419(9) Uani 1 1 d . . . . .
O006 O 0.51338(17) 0.4937(4) 0.80960(14) 0.0357(9) Uani 1 1 d . . . . .
O007 O 0.8470(2) 0.3967(5) 0.35756(17) 0.0426(10) Uani 1 1 d . . . . .
O008 O 0.70223(18) 0.5969(4) 0.48490(16) 0.0402(8) Uani 1 1 d . . . . .
O009 O 0.55730(19) 0.8668(5) 0.47455(14) 0.0399(10) Uani 1 1 d . . . . .
O00A O 0.92082(19) 0.9076(5) 0.50472(17) 0.0462(11) Uani 1 1 d . . . . .
O00B O 0.83480(17) 0.6056(4) 0.14884(15) 0.0455(9) Uani 1 1 d . . . . .
O00C O 0.82108(19) 0.1353(4) 0.31980(16) 0.0396(9) Uani 1 1 d . . . . .
O00D O 1.08055(19) 0.4761(5) 0.31563(16) 0.0413(10) Uani 1 1 d . . . . .
N00E N 0.6347(2) 0.7945(5) 0.62101(17) 0.0196(8) Uani 1 1 d . . . . .
O00F O 1.03111(18) 0.7225(4) 0.49157(15) 0.0441(9) Uani 1 1 d . . . . .
N00G N 0.72106(19) 0.0566(5) 0.53628(17) 0.0211(9) Uani 1 1 d . . . . .
N00H N 0.7542(2) 0.0607(5) 0.46344(19) 0.0208(10) Uani 1 1 d . . . . .
O00I O 0.4324(2) 0.3897(6) 0.65287(18) 0.0523(11) Uani 1 1 d . . . . .
N00J N 0.6898(2) 0.2594(6) 0.63815(19) 0.0272(10) Uani 1 1 d . . . . .
N00K N 1.0644(2) 0.6257(6) 0.32618(17) 0.0269(11) Uani 1 1 d . . . . .
N00L N 0.8181(2) 0.2533(5) 0.36738(19) 0.0244(10) Uani 1 1 d . . . . .
O00M O 0.8414(2) 0.5660(5) 0.53327(18) 0.0527(10) Uani 1 1 d . . . . .
N00N N 0.58473(19) 0.5654(4) 0.79155(16) 0.0214(9) Uani 1 1 d . . . . .
N00O N 0.4303(2) 0.5438(6) 0.65312(17) 0.0278(10) Uani 1 1 d . . . . .
N00P N 0.83557(18) 0.7865(4) 0.37221(16) 0.0222(8) Uani 1 1 d . . . . .
O00Q O 0.36201(18) 0.6340(5) 0.65304(17) 0.0511(11) Uani 1 1 d . . . . .
N00R N 0.65392(18) 0.7481(5) 0.69625(16) 0.0205(8) Uani 1 1 d . . . . .
N00S N 0.82391(19) 0.7345(4) 0.29678(16) 0.0213(8) Uani 1 1 d . . . . .
N00T N 0.51881(19) 0.7595(5) 0.51407(17) 0.0246(9) Uani 1 1 d . . . . .
O00U O 0.6654(2) 0.1445(5) 0.68108(17) 0.0541(11) Uani 1 1 d . . . . .
N00V N 0.7677(2) 0.5091(5) 0.50769(16) 0.0272(9) Uani 1 1 d . . . . .
N00W N 0.9072(2) 0.6105(5) 0.18865(17) 0.0289(10) Uani 1 1 d . . . . .
N00X N 0.9616(2) 0.7989(5) 0.46857(18) 0.0288(10) Uani 1 1 d . . . . .
C00Y C 0.5832(2) 0.6490(5) 0.71578(19) 0.0186(10) Uani 1 1 d . . . . .
C00Z C 0.7226(2) 0.2158(6) 0.5605(2) 0.0193(10) Uani 1 1 d . . . . .
C010 C 0.5548(2) 0.7282(5) 0.59397(19) 0.0201(10) Uani 1 1 d . . . . .
C011 C 0.7785(2) 0.2179(6) 0.4429(2) 0.0193(11) Uani 1 1 d . . . . .
C012 C 0.9689(2) 0.6799(5) 0.3279(2) 0.0204(10) Uani 1 1 d . . . . .
C013 C 0.5180(2) 0.6340(5) 0.6535(2) 0.0197(10) Uani 1 1 d . . . . .
C014 C 0.9241(2) 0.7542(5) 0.39041(19) 0.0206(10) Uani 1 1 d . . . . .
C015 C 0.9021(2) 0.6709(5) 0.26884(19) 0.0200(10) Uani 1 1 d . . . . .
C016 C 0.7577(2) 0.3259(6) 0.5040(2) 0.0192(11) Uani 1 1 d . . . . .
H00H H 0.768(3) -0.036(7) 0.436(2) 0.028(12) Uiso 1 1 d . . . . .
H00S H 0.766(3) 0.739(7) 0.270(3) 0.078(17) Uiso 1 1 d . . . . .
H00E H 0.668(3) 0.863(7) 0.593(2) 0.038(13) 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
O001 N00N 1.214(3) . ?
O002 N00J 1.219(5) . ?
O003 N00W 1.218(4) . ?
O004 N00T 1.222(4) . ?
O005 N00K 1.226(5) . ?
O006 N00N 1.221(4) . ?
O007 N00L 1.210(5) . ?
O008 N00V 1.219(4) . ?
O009 N00T 1.215(4) . ?
O00A N00X 1.208(4) . ?
O00B N00W 1.220(3) . ?
O00C N00L 1.220(5) . ?
O00D N00K 1.206(5) . ?
N00E N00R 1.329(4) . ?
N00E C010 1.330(4) . ?
N00E H00E 0.87(4) . ?
O00F N00X 1.219(4) . ?
N00G N00H 1.324(5) . ?
N00G C00Z 1.309(5) . ?
N00H C011 1.327(6) . ?
N00H H00H 0.91(4) . ?
O00I N00O 1.205(5) . ?
N00J O00U 1.210(5) . ?
N00J C00Z 1.439(5) . ?
N00K C012 1.445(5) . ?
N00L C011 1.431(5) . ?
O00M N00V 1.218(4) . ?
N00N C00Y 1.425(4) . ?
N00O O00Q 1.212(5) . ?
N00O C013 1.450(5) . ?
N00P N00S 1.330(4) . ?
N00P C014 1.329(4) . ?
N00R C00Y 1.332(5) . ?
N00S C015 1.334(4) . ?
N00S H00S 0.93(4) . ?
N00T C010 1.437(4) . ?
N00V C016 1.440(6) . ?
N00W C015 1.425(4) . ?
N00X C014 1.439(4) . ?
C00Y C013 1.385(4) . ?
C00Z C016 1.387(6) . ?
C010 C013 1.360(5) . ?
C011 C016 1.366(6) . ?
C012 C014 1.377(5) . ?
C012 C015 1.359(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
N00R N00E C010 111.5(3) . . ?
N00R N00E H00E 125(2) . . ?
C010 N00E H00E 124(2) . . ?
C00Z N00G N00H 104.9(3) . . ?
N00G N00H C011 111.6(4) . . ?
N00G N00H H00H 122(3) . . ?
C011 N00H H00H 125(3) . . ?
O002 N00J C00Z 116.1(4) . . ?
O00U N00J O002 125.8(4) . . ?
O00U N00J C00Z 118.1(5) . . ?
O005 N00K C012 115.6(4) . . ?
O00D N00K O005 125.9(4) . . ?
O00D N00K C012 118.5(3) . . ?
O007 N00L O00C 126.3(4) . . ?
O007 N00L C011 116.7(4) . . ?
O00C N00L C011 117.0(4) . . ?
O001 N00N O006 126.0(3) . . ?
O001 N00N C00Y 117.6(3) . . ?
O006 N00N C00Y 116.3(3) . . ?
O00I N00O O00Q 127.0(4) . . ?
O00I N00O C013 117.7(3) . . ?
O00Q N00O C013 115.4(4) . . ?
C014 N00P N00S 104.3(3) . . ?
N00E N00R C00Y 104.7(3) . . ?
N00P N00S C015 111.4(3) . . ?
N00P N00S H00S 122(3) . . ?
C015 N00S H00S 127(3) . . ?
O004 N00T C010 116.1(3) . . ?
O009 N00T O004 126.1(3) . . ?
O009 N00T C010 117.7(3) . . ?
O008 N00V C016 118.1(3) . . ?
O00M N00V O008 124.3(4) . . ?
O00M N00V C016 117.6(3) . . ?
O003 N00W O00B 126.7(3) . . ?
O003 N00W C015 116.5(3) . . ?
O00B N00W C015 116.8(3) . . ?
O00A N00X O00F 126.7(3) . . ?
O00A N00X C014 116.7(3) . . ?
O00F N00X C014 116.6(3) . . ?
N00R C00Y N00N 119.8(3) . . ?
N00R C00Y C013 111.9(3) . . ?
C013 C00Y N00N 128.2(3) . . ?
N00G C00Z N00J 120.1(4) . . ?
N00G C00Z C016 112.5(4) . . ?
C016 C00Z N00J 127.4(5) . . ?
N00E C010 N00T 122.1(3) . . ?
N00E C010 C013 108.6(3) . . ?
C013 C010 N00T 129.3(3) . . ?
N00H C011 N00L 121.7(4) . . ?
N00H C011 C016 108.2(4) . . ?
C016 C011 N00L 130.2(4) . . ?
C014 C012 N00K 127.9(3) . . ?
C015 C012 N00K 128.7(3) . . ?
C015 C012 C014 103.4(3) . . ?
C00Y C013 N00O 128.0(3) . . ?
C010 C013 N00O 128.7(3) . . ?
C010 C013 C00Y 103.3(3) . . ?
N00P C014 N00X 119.3(3) . . ?
N00P C014 C012 112.4(3) . . ?
C012 C014 N00X 128.2(3) . . ?
N00S C015 N00W 121.7(3) . . ?
N00S C015 C012 108.4(3) . . ?
C012 C015 N00W 129.9(3) . . ?
C00Z C016 N00V 128.8(4) . . ?
C011 C016 N00V 128.5(4) . . ?
C011 C016 C00Z 102.7(4) . . ?

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
O001 N00N C00Y N00R -9.8(5) . . . . ?
O001 N00N C00Y C013 165.7(4) . . . . ?
O002 N00J C00Z N00G -177.1(3) . . . . ?
O002 N00J C00Z C016 2.8(5) . . . . ?
O003 N00W C015 N00S 174.1(4) . . . . ?
O003 N00W C015 C012 -4.4(7) . . . . ?
O004 N00T C010 N00E 170.3(4) . . . . ?
O004 N00T C010 C013 -10.1(7) . . . . ?
O005 N00K C012 C014 -61.8(5) . . . . ?
O005 N00K C012 C015 117.9(5) . . . . ?
O006 N00N C00Y N00R 171.4(4) . . . . ?
O006 N00N C00Y C013 -13.1(6) . . . . ?
O007 N00L C011 N00H -172.4(3) . . . . ?
O007 N00L C011 C016 8.5(6) . . . . ?
O008 N00V C016 C00Z -87.4(4) . . . . ?
O008 N00V C016 C011 90.8(4) . . . . ?
O009 N00T C010 N00E -9.4(6) . . . . ?
O009 N00T C010 C013 170.1(5) . . . . ?
O00A N00X C014 N00P -21.9(7) . . . . ?
O00A N00X C014 C012 157.6(5) . . . . ?
O00B N00W C015 N00S -6.3(6) . . . . ?
O00B N00W C015 C012 175.3(4) . . . . ?
O00C N00L C011 N00H 6.3(5) . . . . ?
O00C N00L C011 C016 -172.9(3) . . . . ?
O00D N00K C012 C014 118.0(5) . . . . ?
O00D N00K C012 C015 -62.3(6) . . . . ?
N00E N00R C00Y N00N 175.2(3) . . . . ?
N00E N00R C00Y C013 -0.9(5) . . . . ?
N00E C010 C013 N00O 177.3(4) . . . . ?
N00E C010 C013 C00Y -1.0(5) . . . . ?
O00F N00X C014 N00P 157.9(4) . . . . ?
O00F N00X C014 C012 -22.6(7) . . . . ?
N00G N00H C011 N00L 178.6(3) . . . . ?
N00G N00H C011 C016 -2.1(4) . . . . ?
N00G C00Z C016 N00V 178.0(3) . . . . ?
N00G C00Z C016 C011 -0.6(4) . . . . ?
N00H N00G C00Z N00J 179.2(3) . . . . ?
N00H N00G C00Z C016 -0.6(4) . . . . ?
N00H C011 C016 N00V -177.0(3) . . . . ?
N00H C011 C016 C00Z 1.6(4) . . . . ?
O00I N00O C013 C00Y -72.0(5) . . . . ?
O00I N00O C013 C010 110.1(5) . . . . ?
N00J C00Z C016 N00V -1.9(6) . . . . ?
N00J C00Z C016 C011 179.6(3) . . . . ?
N00K C012 C014 N00P -179.3(4) . . . . ?
N00K C012 C014 N00X 1.2(7) . . . . ?
N00K C012 C015 N00S 179.6(4) . . . . ?
N00K C012 C015 N00W -1.8(8) . . . . ?
N00L C011 C016 N00V 2.2(6) . . . . ?
N00L C011 C016 C00Z -179.2(3) . . . . ?
O00M N00V C016 C00Z 92.8(4) . . . . ?
O00M N00V C016 C011 -89.0(4) . . . . ?
N00N C00Y C013 N00O 7.2(7) . . . . ?
N00N C00Y C013 C010 -174.6(4) . . . . ?
N00P N00S C015 N00W -178.5(4) . . . . ?
N00P N00S C015 C012 0.2(5) . . . . ?
O00Q N00O C013 C00Y 108.0(5) . . . . ?
O00Q N00O C013 C010 -69.8(5) . . . . ?
N00R N00E C010 N00T -179.9(4) . . . . ?
N00R N00E C010 C013 0.5(5) . . . . ?
N00R C00Y C013 N00O -177.1(4) . . . . ?
N00R C00Y C013 C010 1.2(5) . . . . ?
N00S N00P C014 N00X 178.7(4) . . . . ?
N00S N00P C014 C012 -0.9(5) . . . . ?
N00T C010 C013 N00O -2.3(8) . . . . ?
N00T C010 C013 C00Y 179.4(4) . . . . ?
O00U N00J C00Z N00G 3.6(5) . . . . ?
O00U N00J C00Z C016 -176.6(4) . . . . ?
C00Z N00G N00H C011 1.7(4) . . . . ?
C010 N00E N00R C00Y 0.3(5) . . . . ?
C014 N00P N00S C015 0.4(4) . . . . ?
C014 C012 C015 N00S -0.7(4) . . . . ?
C014 C012 C015 N00W 177.9(4) . . . . ?
C015 C012 C014 N00P 1.0(5) . . . . ?
C015 C012 C014 N00X -178.5(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_2tnp_p07
_audit_block_doi                 10.5517/ccdc.csd.cc29gp7q
_database_code_depnum_ccdc_archive 'CCDC 2129273'
loop_
_audit_author_name
_audit_author_address
'Liu X.'
;The University of Edinburgh
United Kingdom
;
_audit_update_record             
;
2021-12-16 deposited with the CCDC.	2023-11-20 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT029_2tnp_p07            
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.549 Why?
RESPONSE: high pressure data
;
_vrf_PLAT088_2tnp_p07            
;
PROBLEM: Poor Data / Parameter Ratio ....................       4.81 Note
RESPONSE: high pressure data
;
# Added during the CSD deposition process: Thursday 16 December 2021 05:11 PM
# end Validation Reply Form

_audit_creation_date             2021-12-16
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
?
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '3(C3 H N5 O6)'
_chemical_formula_sum            'C9 H3 N15 O18'
_chemical_formula_weight         609.26
_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                   14.2569(7)
_cell_length_b                   7.6573(6)
_cell_length_c                   16.6118(8)
_cell_angle_alpha                90
_cell_angle_beta                 92.197(3)
_cell_angle_gamma                90
_cell_volume                     1812.17(19)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3466
_cell_measurement_temperature    298.4
_cell_measurement_theta_max      24.19
_cell_measurement_theta_min      2.79
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.217
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6715
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0553 before and 0.0469 after correction.
The Ratio of minimum to maximum transmission is 0.9009.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.233
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1224
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0409
_diffrn_reflns_av_unetI/netI     0.0378
_diffrn_reflns_Laue_measured_fraction_full 0.549
_diffrn_reflns_Laue_measured_fraction_max 0.508
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            10484
_diffrn_reflns_point_group_measured_fraction_full 0.549
_diffrn_reflns_point_group_measured_fraction_max 0.508
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.286
_diffrn_reflns_theta_min         2.454
_diffrn_ambient_temperature      298.4
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.549
_diffrn_measured_fraction_theta_max 0.508
_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                1468
_reflns_number_total             1871
_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 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.176
_refine_diff_density_min         -0.177
_refine_diff_density_rms         0.046
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_matrix_type           full
_refine_ls_number_parameters     389
_refine_ls_number_reflns         1871
_refine_ls_number_restraints     306
_refine_ls_R_factor_all          0.0546
_refine_ls_R_factor_gt           0.0366
_refine_ls_restrained_S_all      0.960
_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)+(0.0665P)²+1.0412P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0969
_refine_ls_wR_factor_ref         0.1071
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups
2. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
;
_atom_sites_solution_hydrogens   difmap
_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
O001 O 0.44797(16) 1.1637(4) 0.48725(13) 0.0317(8) Uani 1 1 d . . . . .
O002 O 0.81916(17) 0.6352(4) 0.31889(13) 0.0329(8) Uani 1 1 d . . . . .
O003 O 1.12074(16) 0.2611(4) 0.33139(14) 0.0361(8) Uani 1 1 d . . . . .
O004 O 0.70940(17) 1.1060(4) 0.48802(14) 0.0339(8) Uani 1 1 d . . . . .
O005 O 0.91841(18) 0.4179(5) 0.50045(15) 0.0376(9) Uani 1 1 d . . . . .
O006 O 0.65307(15) 1.0573(4) 0.82932(12) 0.0297(8) Uani 1 1 d . . . . .
O007 O 0.85712(19) 0.8947(5) 0.36143(15) 0.0378(9) Uani 1 1 d . . . . .
O008 O 0.55328(18) 1.3650(4) 0.47110(13) 0.0361(9) Uani 1 1 d . . . . .
O009 O 0.50658(17) 0.9895(4) 0.80762(13) 0.0337(9) Uani 1 1 d . . . . .
O1 O 1.08499(18) -0.0095(5) 0.31049(15) 0.0349(9) Uani 1 1 d . . . . .
O00B O 0.69609(18) 0.9144(5) 0.65892(14) 0.0361(9) Uani 1 1 d . . . . .
O00C O 0.98453(17) 0.0900(4) 0.16068(14) 0.0351(9) Uani 1 1 d . . . . .
O2 O 0.83272(16) 0.1209(4) 0.14173(13) 0.0368(9) Uani 1 1 d . . . . .
N00E N 0.71736(18) 0.5542(5) 0.53655(14) 0.0192(8) Uani 1 1 d . . . . .
O00F O 0.4234(2) 0.8809(5) 0.65202(16) 0.0447(10) Uani 1 1 d . . . . .
O00G O 1.03037(17) 0.2274(4) 0.48835(14) 0.0385(8) Uani 1 1 d . . . . .
N00H N 0.63158(19) 1.2915(5) 0.61828(15) 0.0180(8) Uani 1 1 d . . . . .
N00I N 1.0652(2) 0.1405(5) 0.32108(15) 0.0209(9) Uani 1 1 d . . . . .
O00J O 0.8507(2) 1.0670(5) 0.53615(17) 0.0508(10) Uani 1 1 d . . . . .
N00K N 0.4234(2) 1.0387(6) 0.65059(15) 0.0235(9) Uani 1 1 d . . . . .
N00L N 0.82141(19) 0.7518(5) 0.36890(16) 0.0215(9) Uani 1 1 d . . . . .
N00M N 0.75045(19) 0.5571(5) 0.46289(17) 0.0181(9) Uani 1 1 d . . . . .
O00N O 0.35525(17) 1.1336(5) 0.65071(15) 0.0450(10) Uani 1 1 d . . . . .
N00O N 0.83020(18) 0.2833(4) 0.36979(15) 0.0198(8) Uani 1 1 d . . . . .
N00P N 0.69288(19) 0.7612(6) 0.64123(16) 0.0245(9) Uani 1 1 d . . . . .
N00Q N 0.58014(19) 1.0579(4) 0.78961(15) 0.0198(8) Uani 1 1 d . . . . .
N00R N 0.81865(19) 0.2313(4) 0.29345(15) 0.0198(8) Uani 1 1 d . . . . .
N00S N 0.65021(18) 1.2456(4) 0.69431(14) 0.0178(8) Uani 1 1 d . . . . .
N00T N 0.7751(2) 1.0133(5) 0.51103(15) 0.0243(8) Uani 1 1 d . . . . .
O00U O 0.6674(2) 0.6423(5) 0.68377(15) 0.0517(10) Uani 1 1 d . . . . .
N00V N 0.90617(19) 0.1244(5) 0.18216(15) 0.0238(9) Uani 1 1 d . . . . .
N00W N 0.51528(19) 1.2547(5) 0.51000(15) 0.0223(8) Uani 1 1 d . . . . .
N00X N 0.9593(2) 0.3043(5) 0.46544(16) 0.0260(9) Uani 1 1 d . . . . .
C00Y C 0.7234(2) 0.7158(6) 0.56240(18) 0.0181(9) Uani 1 1 d . . . . .
C00Z C 0.5508(2) 1.2224(5) 0.59045(17) 0.0172(9) Uani 1 1 d . . . . .
C010 C 0.5785(2) 1.1442(5) 0.71352(18) 0.0170(9) Uani 1 1 d . . . . .
C011 C 0.5131(2) 1.1268(5) 0.65040(18) 0.0174(9) Uani 1 1 d . . . . .
C012 C 0.8992(2) 0.1751(5) 0.26427(17) 0.0169(9) Uani 1 1 d . . . . .
C013 C 0.9676(2) 0.1885(5) 0.32365(18) 0.0167(9) Uani 1 1 d . . . . .
C014 C 0.7625(2) 0.8281(6) 0.50705(18) 0.0183(9) Uani 1 1 d . . . . .
C015 C 0.9207(2) 0.2572(5) 0.38684(18) 0.0179(10) Uani 1 1 d . . . . .
C016 C 0.7797(2) 0.7160(6) 0.44382(18) 0.0180(10) Uani 1 1 d . . . . .
H00R H 0.762(2) 0.236(5) 0.2687(17) 0.022 Uiso 1 1 d . U . . .
H00H H 0.665(3) 1.365(6) 0.593(2) 0.022 Uiso 1 1 d . U . . .
H00M H 0.761(3) 0.465(7) 0.433(2) 0.040(13) 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
O001 N00W 1.233(4) . ?
O002 N00L 1.219(4) . ?
O003 N00I 1.225(4) . ?
O004 N00T 1.225(4) . ?
O005 N00X 1.209(4) . ?
O006 N00Q 1.210(3) . ?
O007 N00L 1.215(4) . ?
O008 N00W 1.205(4) . ?
O009 N00Q 1.220(4) . ?
O1 N00I 1.198(4) . ?
O00B N00P 1.210(4) . ?
O00C N00V 1.215(3) . ?
O2 N00V 1.223(3) . ?
N00E N00M 1.328(4) . ?
N00E C00Y 1.312(5) . ?
O00F N00K 1.208(4) . ?
O00G N00X 1.219(4) . ?
N00H N00S 1.328(4) . ?
N00H C00Z 1.334(4) . ?
N00H H00H 0.85(4) . ?
N00I C013 1.440(4) . ?
O00J N00T 1.213(4) . ?
N00K O00N 1.213(4) . ?
N00K C011 1.447(4) . ?
N00L C016 1.426(4) . ?
N00M C016 1.329(6) . ?
N00M H00M 0.88(5) . ?
N00O N00R 1.333(4) . ?
N00O C015 1.325(4) . ?
N00P O00U 1.217(5) . ?
N00P C00Y 1.438(4) . ?
N00Q C010 1.426(4) . ?
N00R C012 1.335(4) . ?
N00R H00R 0.89(3) . ?
N00S C010 1.332(4) . ?
N00T C014 1.430(5) . ?
N00V C012 1.425(4) . ?
N00W C00Z 1.432(4) . ?
N00X C015 1.443(4) . ?
C00Y C014 1.391(5) . ?
C00Z C011 1.363(5) . ?
C010 C011 1.382(4) . ?
C012 C013 1.364(4) . ?
C013 C015 1.371(5) . ?
C014 C016 1.386(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
C00Y N00E N00M 105.3(3) . . ?
N00S N00H C00Z 111.3(3) . . ?
N00S N00H H00H 123(2) . . ?
C00Z N00H H00H 125(2) . . ?
O003 N00I C013 115.0(4) . . ?
O1 N00I O003 126.1(4) . . ?
O1 N00I C013 118.9(3) . . ?
O00F N00K O00N 126.8(4) . . ?
O00F N00K C011 117.8(3) . . ?
O00N N00K C011 115.4(4) . . ?
O002 N00L C016 117.0(3) . . ?
O007 N00L O002 126.1(3) . . ?
O007 N00L C016 116.9(3) . . ?
N00E N00M C016 111.2(3) . . ?
N00E N00M H00M 126(3) . . ?
C016 N00M H00M 122(3) . . ?
C015 N00O N00R 104.0(3) . . ?
O00B N00P O00U 126.5(4) . . ?
O00B N00P C00Y 116.4(3) . . ?
O00U N00P C00Y 117.1(4) . . ?
O006 N00Q O009 126.4(3) . . ?
O006 N00Q C010 118.0(3) . . ?
O009 N00Q C010 115.6(3) . . ?
N00O N00R C012 111.4(3) . . ?
N00O N00R H00R 120(2) . . ?
C012 N00R H00R 128.4(19) . . ?
N00H N00S C010 104.8(3) . . ?
O004 N00T C014 117.9(3) . . ?
O00J N00T O004 124.7(4) . . ?
O00J N00T C014 117.4(3) . . ?
O00C N00V O2 127.7(3) . . ?
O00C N00V C012 116.0(3) . . ?
O2 N00V C012 116.2(3) . . ?
O001 N00W C00Z 115.6(3) . . ?
O008 N00W O001 126.3(3) . . ?
O008 N00W C00Z 118.1(3) . . ?
O005 N00X O00G 127.4(3) . . ?
O005 N00X C015 116.1(3) . . ?
O00G N00X C015 116.5(3) . . ?
N00E C00Y N00P 120.5(3) . . ?
N00E C00Y C014 112.9(3) . . ?
C014 C00Y N00P 126.5(4) . . ?
N00H C00Z N00W 121.6(3) . . ?
N00H C00Z C011 108.6(3) . . ?
C011 C00Z N00W 129.8(3) . . ?
N00S C010 N00Q 119.7(3) . . ?
N00S C010 C011 112.1(3) . . ?
C011 C010 N00Q 128.0(3) . . ?
C00Z C011 N00K 128.7(3) . . ?
C00Z C011 C010 103.3(3) . . ?
C010 C011 N00K 127.9(3) . . ?
N00R C012 N00V 121.9(3) . . ?
N00R C012 C013 108.3(3) . . ?
C013 C012 N00V 129.7(3) . . ?
C012 C013 N00I 128.6(3) . . ?
C012 C013 C015 103.1(3) . . ?
C015 C013 N00I 128.4(3) . . ?
C00Y C014 N00T 129.4(3) . . ?
C016 C014 N00T 128.6(3) . . ?
C016 C014 C00Y 101.9(4) . . ?
N00O C015 N00X 119.4(3) . . ?
N00O C015 C013 113.2(3) . . ?
C013 C015 N00X 127.4(3) . . ?
N00M C016 N00L 121.9(4) . . ?
N00M C016 C014 108.7(3) . . ?
C014 C016 N00L 129.4(4) . . ?

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
O001 N00W C00Z N00H 169.5(4) . . . . ?
O001 N00W C00Z C011 -11.7(6) . . . . ?
O002 N00L C016 N00M 8.4(5) . . . . ?
O002 N00L C016 C014 -171.7(3) . . . . ?
O003 N00I C013 C012 118.2(4) . . . . ?
O003 N00I C013 C015 -62.6(5) . . . . ?
O004 N00T C014 C00Y -85.5(4) . . . . ?
O004 N00T C014 C016 88.9(4) . . . . ?
O005 N00X C015 N00O -25.7(6) . . . . ?
O005 N00X C015 C013 153.0(4) . . . . ?
O006 N00Q C010 N00S -11.5(5) . . . . ?
O006 N00Q C010 C011 162.7(4) . . . . ?
O007 N00L C016 N00M -170.5(3) . . . . ?
O007 N00L C016 C014 9.4(5) . . . . ?
O008 N00W C00Z N00H -10.0(6) . . . . ?
O008 N00W C00Z C011 168.8(4) . . . . ?
O009 N00Q C010 N00S 169.4(4) . . . . ?
O009 N00Q C010 C011 -16.4(5) . . . . ?
O1 N00I C013 C012 -62.8(5) . . . . ?
O1 N00I C013 C015 116.4(4) . . . . ?
O00B N00P C00Y N00E -176.2(3) . . . . ?
O00B N00P C00Y C014 5.1(5) . . . . ?
O00C N00V C012 N00R 173.9(3) . . . . ?
O00C N00V C012 C013 -1.1(6) . . . . ?
O2 N00V C012 N00R -6.1(5) . . . . ?
O2 N00V C012 C013 178.9(4) . . . . ?
N00E N00M C016 N00L 177.7(3) . . . . ?
N00E N00M C016 C014 -2.2(4) . . . . ?
N00E C00Y C014 N00T 175.6(3) . . . . ?
N00E C00Y C014 C016 0.1(4) . . . . ?
O00F N00K C011 C00Z 112.1(4) . . . . ?
O00F N00K C011 C010 -72.9(5) . . . . ?
O00G N00X C015 N00O 155.6(4) . . . . ?
O00G N00X C015 C013 -25.7(6) . . . . ?
N00H N00S C010 N00Q 174.2(3) . . . . ?
N00H N00S C010 C011 -0.9(4) . . . . ?
N00H C00Z C011 N00K 175.0(4) . . . . ?
N00H C00Z C011 C010 -0.8(4) . . . . ?
N00I C013 C015 N00O -178.6(4) . . . . ?
N00I C013 C015 N00X 2.7(7) . . . . ?
O00J N00T C014 C00Y 95.3(4) . . . . ?
O00J N00T C014 C016 -90.2(4) . . . . ?
N00M N00E C00Y N00P 179.8(3) . . . . ?
N00M N00E C00Y C014 -1.3(3) . . . . ?
O00N N00K C011 C00Z -69.1(5) . . . . ?
O00N N00K C011 C010 105.8(4) . . . . ?
N00O N00R C012 N00V -175.5(3) . . . . ?
N00O N00R C012 C013 0.5(4) . . . . ?
N00P C00Y C014 N00T -5.5(6) . . . . ?
N00P C00Y C014 C016 178.9(3) . . . . ?
N00Q C010 C011 N00K 10.6(6) . . . . ?
N00Q C010 C011 C00Z -173.5(4) . . . . ?
N00R N00O C015 N00X 178.4(3) . . . . ?
N00R N00O C015 C013 -0.5(4) . . . . ?
N00R C012 C013 N00I 178.6(4) . . . . ?
N00R C012 C013 C015 -0.7(4) . . . . ?
N00S N00H C00Z N00W 179.4(3) . . . . ?
N00S N00H C00Z C011 0.4(5) . . . . ?
N00S C010 C011 N00K -174.9(4) . . . . ?
N00S C010 C011 C00Z 1.1(4) . . . . ?
N00T C014 C016 N00L 5.7(6) . . . . ?
N00T C014 C016 N00M -174.4(3) . . . . ?
O00U N00P C00Y N00E 4.6(5) . . . . ?
O00U N00P C00Y C014 -174.2(3) . . . . ?
N00V C012 C013 N00I -5.9(7) . . . . ?
N00V C012 C013 C015 174.8(4) . . . . ?
N00W C00Z C011 N00K -3.9(7) . . . . ?
N00W C00Z C011 C010 -179.8(4) . . . . ?
C00Y N00E N00M C016 2.1(3) . . . . ?
C00Y C014 C016 N00L -178.7(3) . . . . ?
C00Y C014 C016 N00M 1.2(4) . . . . ?
C00Z N00H N00S C010 0.3(4) . . . . ?
C012 C013 C015 N00O 0.8(4) . . . . ?
C012 C013 C015 N00X -178.0(4) . . . . ?
C015 N00O N00R C012 0.0(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_2tnp_p10_h
_audit_block_doi                 10.5517/ccdc.csd.cc29gp8r
_database_code_depnum_ccdc_archive 'CCDC 2129274'
loop_
_audit_author_name
_audit_author_address
'Liu X.'
;The University of Edinburgh
United Kingdom
;
_audit_update_record             
;
2021-12-16 deposited with the CCDC.	2023-11-20 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT029_2tnp_p10_h          
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.550 Why?
RESPONSE: high pressure data
;
_vrf_PLAT089_2tnp_p10_h          
;
PROBLEM: Poor Data / Parameter Ratio (Zmax < 18) ........       2.15 Note
RESPONSE: high pressure data
;
_vrf_PLAT211_2tnp_p10_h          
;
PROBLEM: ADP of Atom C00W      is N.P.D. or (nearly) 2D .     Please Check
RESPONSE: high pressure data
;
_vrf_PLAT213_2tnp_p10_h          
;
PROBLEM: Atom C00M            has ADP max/min Ratio .....        5.1 oblate
RESPONSE: high pressure data
;
# Added during the CSD deposition process: Thursday 16 December 2021 05:11 PM
# end Validation Reply Form

_audit_creation_date             2021-12-16
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
?
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '6(C3 N5 O6)'
_chemical_formula_sum            'C18 N30 O36'
_chemical_formula_weight         1212.48
_chemical_absolute_configuration ?
_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'
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           9
_space_group_name_H-M_alt        'C 1 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'

_cell_length_a                   19.319(2)
_cell_length_b                   7.5668(13)
_cell_length_c                   14.458(3)
_cell_angle_alpha                90
_cell_angle_beta                 127.623(5)
_cell_angle_gamma                90
_cell_volume                     1674.0(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1713
_cell_measurement_temperature    287.2
_cell_measurement_theta_max      24.47
_cell_measurement_theta_min      2.86
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.235
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6076
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.405
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1212
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0320
_diffrn_reflns_av_unetI/netI     0.0488
_diffrn_reflns_Laue_measured_fraction_full 0.550
_diffrn_reflns_Laue_measured_fraction_max 0.550
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            3579
_diffrn_reflns_point_group_measured_fraction_full 0.506
_diffrn_reflns_point_group_measured_fraction_max 0.505
_diffrn_reflns_theta_full        25.022
_diffrn_reflns_theta_max         25.022
_diffrn_reflns_theta_min         2.662
_diffrn_ambient_temperature      287.2
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.550
_diffrn_measured_fraction_theta_max 0.550
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.836
_reflns_Friedel_fraction_full    0.461
_reflns_Friedel_fraction_max     0.461
_reflns_number_gt                1292
_reflns_number_total             1493
_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 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.227
_refine_diff_density_min         -0.259
_refine_diff_density_rms         0.062
_refine_ls_abs_structure_details 
;
 Flack x determined using 539 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -2.4(10)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    undef
_refine_ls_matrix_type           full
_refine_ls_number_parameters     379
_refine_ls_number_reflns         1493
_refine_ls_number_restraints     317
_refine_ls_R_factor_all          0.0522
_refine_ls_R_factor_gt           0.0416
_refine_ls_restrained_S_all      0.920
_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)+(0.0927P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1072
_refine_ls_wR_factor_ref         0.1137
_refine_special_details          ?
_olex2_refinement_description    
;
1. Restrained distances
 C00W-C00M \\sim C00W-C00I
 with sigma of 0.02
 N4-C00M \\sim N00A-C00I
 with sigma of 0.02
 C00M-N4 \\sim C00I-N00A
 with sigma of 0.02
 C00I-N00A \\sim N4-C00M
 with sigma of 0.05
 N4-C00M \\sim N9-C00V
 with sigma of 0.02
 N00A-C00I \\sim N4-C00M
 with sigma of 0.1
 C00W-C00I \\sim C00W-C00M
 with sigma of 0.1
2. Restrained planarity
 N00A, C00I, C00W, C00M, N4
 with sigma of 0.1
3. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
;
_atom_sites_solution_hydrogens   .
_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
O001 O 0.2917(6) 0.1935(16) 0.4295(8) 0.030(3) Uani 1 1 d . . . . .
N11 N 0.0161(7) 0.698(2) 0.1817(9) 0.020(4) Uani 1 1 d . . . . .
O003 O 0.6253(5) 0.6173(17) 0.5360(7) 0.027(3) Uani 1 1 d . . . . .
O004 O 0.4914(7) -0.1642(19) 0.4560(9) 0.035(4) Uani 1 1 d . . . . .
O005 O 0.8208(6) 0.9176(18) 0.8916(8) 0.035(3) Uani 1 1 d . . . . .
N14 N 0.1277(6) 0.897(2) 0.3302(9) 0.022(3) Uani 1 1 d . . . . .
O007 O 0.6519(5) 0.8045(16) 0.6678(7) 0.031(3) Uani 1 1 d . . . . .
N2 N 0.3439(8) 0.114(2) 0.4247(11) 0.023(3) Uani 1 1 d . . . . .
O009 O 0.9848(6) 1.0258(18) 0.8489(9) 0.027(3) Uani 1 1 d . . . . .
N00A N 0.7919(6) 0.6303(19) 0.6188(9) 0.027(4) Uani 1 1 d D . . . .
C9 C 0.4974(8) 0.134(2) 0.4871(11) 0.022(3) Uani 1 1 d . . . . .
O12 O 0.3298(6) 0.5215(19) 0.5770(8) 0.026(3) Uani 1 1 d . . . . .
O13 O 0.3516(5) 0.7928(17) 0.6395(8) 0.027(3) Uani 1 1 d . . . . .
O00E O 0.1515(6) 0.3625(17) 0.2771(7) 0.033(3) Uani 1 1 d . . . . .
O00F O 0.1698(5) 0.3399(18) 0.4389(7) 0.031(3) Uani 1 1 d . . . . .
N8 N 0.5004(7) -0.014(2) 0.4287(10) 0.025(4) Uani 1 1 d . . . . .
N7 N 0.6727(7) 0.714(2) 0.6205(10) 0.024(3) Uani 1 1 d . . . . .
C00I C 0.7616(7) 0.725(2) 0.6647(9) 0.018(4) Uani 1 1 d D . . . .
O00J O -0.0061(6) 0.5452(18) 0.1545(7) 0.024(3) Uani 1 1 d . . . . .
N4 N 0.8743(7) 0.667(2) 0.6646(10) 0.026(4) Uani 1 1 d D . . . .
N3 N 0.1593(8) 0.4301(18) 0.3612(11) 0.020(3) Uani 1 1 d . . . . .
C00M C 0.8929(7) 0.798(2) 0.7400(10) 0.015(3) Uani 1 1 d D . . . .
N1 N 0.6501(8) 0.245(2) 0.6043(10) 0.023(3) Uani 1 1 d . . . . .
C00O C 0.4280(8) 0.193(3) 0.4809(12) 0.025(4) Uani 1 1 d . . . . .
N6 N 0.9744(7) 0.887(2) 0.7966(9) 0.017(3) Uani 1 1 d . . . . .
C00Q C 0.2272(8) 0.722(2) 0.4595(10) 0.018(3) Uani 1 1 d . . . . .
O17 O 0.8241(6) 1.1207(19) 0.7879(8) 0.030(3) Uani 1 1 d . . . . .
O11 O 0.3303(7) -0.029(2) 0.3722(9) 0.035(4) Uani 1 1 d . . . . .
C10 C 0.1641(9) 0.614(2) 0.3724(12) 0.017(3) Uani 1 1 d . . . . .
O00U O 0.6692(5) 0.1095(17) 0.5737(7) 0.030(3) Uani 1 1 d . . . . .
C00V C 0.5605(7) 0.255(2) 0.5583(10) 0.021(4) Uani 1 1 d D . . . .
C00W C 0.8260(6) 0.834(2) 0.7465(9) 0.015(3) Uani 1 1 d D . . . .
O15 O -0.0258(6) 0.8333(18) 0.1271(8) 0.034(3) Uani 1 1 d . . . . .
O10 O 0.7032(6) 0.3574(19) 0.6728(8) 0.033(3) Uani 1 1 d . . . . .
O14 O 1.0245(5) 0.8306(16) 0.7783(7) 0.022(3) Uani 1 1 d . . . . .
N10 N 0.4508(6) 0.335(2) 0.5441(9) 0.025(3) Uani 1 1 d . . . . .
N9 N 0.5341(7) 0.3796(19) 0.5953(8) 0.025(3) Uani 1 1 d D . . . .
N15 N 0.8236(7) 0.969(2) 0.8139(10) 0.023(4) Uani 1 1 d . . . . .
O16 O 0.5100(6) 0.0205(18) 0.3531(8) 0.042(4) Uani 1 1 d . . . . .
N12 N 0.3095(6) 0.675(2) 0.5685(9) 0.019(3) Uani 1 1 d . . . . .
C12 C 0.1019(8) 0.733(2) 0.2921(10) 0.017(3) Uani 1 1 d . . . . .
N13 N 0.2073(6) 0.892(2) 0.4373(9) 0.022(3) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O001 N2 1.211(16) . ?
N11 O00J 1.215(17) . ?
N11 O15 1.241(17) . ?
N11 C12 1.461(17) . ?
O003 N7 1.227(16) . ?
O004 N8 1.254(19) . ?
O005 N15 1.220(15) . ?
N14 C12 1.325(19) . ?
N14 N13 1.363(13) . ?
O007 N7 1.195(15) . ?
N2 C00O 1.430(19) . ?
N2 O11 1.26(2) . ?
O009 N6 1.236(18) . ?
N00A C00I 1.332(15) . ?
N00A N4 1.327(15) . ?
C9 N8 1.43(2) . ?
C9 C00O 1.364(17) . ?
C9 C00V 1.36(2) . ?
O12 N12 1.208(19) . ?
O13 N12 1.221(17) . ?
O00E N3 1.242(15) . ?
O00F N3 1.221(17) . ?
N8 O16 1.242(15) . ?
N7 C00I 1.423(15) . ?
C00I C00W 1.351(18) . ?
N4 C00M 1.349(18) . ?
N3 C10 1.396(17) . ?
C00M N6 1.427(17) . ?
C00M C00W 1.377(15) . ?
N1 O00U 1.256(17) . ?
N1 C00V 1.427(15) . ?
N1 O10 1.233(19) . ?
C00O N10 1.30(2) . ?
N6 O14 1.226(14) . ?
C00Q C10 1.37(2) . ?
C00Q N12 1.441(16) . ?
C00Q N13 1.33(2) . ?
O17 N15 1.209(19) . ?
C10 C12 1.38(2) . ?
C00V N9 1.329(17) . ?
C00W N15 1.43(2) . ?
N10 N9 1.342(15) . ?

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
O00J N11 O15 128.0(14) . . ?
O00J N11 C12 117.8(12) . . ?
O15 N11 C12 114.2(15) . . ?
C12 N14 N13 108.8(13) . . ?
O001 N2 C00O 117.2(15) . . ?
O001 N2 O11 125.9(14) . . ?
O11 N2 C00O 116.8(13) . . ?
N4 N00A C00I 113.5(11) . . ?
C00O C9 N8 127.8(14) . . ?
C00V C9 N8 129.4(10) . . ?
C00V C9 C00O 102.8(13) . . ?
O004 N8 C9 117.6(13) . . ?
O16 N8 O004 126.2(15) . . ?
O16 N8 C9 116.2(16) . . ?
O003 N7 C00I 116.3(11) . . ?
O007 N7 O003 127.3(11) . . ?
O007 N7 C00I 116.4(12) . . ?
N00A C00I N7 121.5(12) . . ?
N00A C00I C00W 108.2(10) . . ?
C00W C00I N7 130.0(12) . . ?
N00A N4 C00M 101.6(10) . . ?
O00E N3 C10 118.9(11) . . ?
O00F N3 O00E 121.6(14) . . ?
O00F N3 C10 119.3(11) . . ?
N4 C00M N6 117.9(9) . . ?
N4 C00M C00W 113.8(11) . . ?
C00W C00M N6 128.2(12) . . ?
O00U N1 C00V 114.5(13) . . ?
O10 N1 O00U 124.4(11) . . ?
O10 N1 C00V 121.0(13) . . ?
C9 C00O N2 129.1(15) . . ?
N10 C00O N2 121.7(12) . . ?
N10 C00O C9 109.0(13) . . ?
O009 N6 C00M 117.7(11) . . ?
O14 N6 O009 125.0(13) . . ?
O14 N6 C00M 116.7(12) . . ?
C10 C00Q N12 129.1(16) . . ?
N13 C00Q C10 113.2(13) . . ?
N13 C00Q N12 117.7(13) . . ?
C00Q C10 N3 131.3(13) . . ?
C00Q C10 C12 102.3(14) . . ?
C12 C10 N3 126.3(13) . . ?
C9 C00V N1 126.0(14) . . ?
N9 C00V C9 113.2(10) . . ?
N9 C00V N1 120.3(12) . . ?
C00I C00W C00M 102.8(12) . . ?
C00I C00W N15 129.3(10) . . ?
C00M C00W N15 127.5(12) . . ?
C00O N10 N9 111.9(11) . . ?
C00V N9 N10 103.0(11) . . ?
O005 N15 C00W 115.8(17) . . ?
O17 N15 O005 127.1(16) . . ?
O17 N15 C00W 117.1(12) . . ?
O12 N12 O13 127.5(14) . . ?
O12 N12 C00Q 114.8(12) . . ?
O13 N12 C00Q 117.7(17) . . ?
N14 C12 N11 120.8(13) . . ?
N14 C12 C10 110.5(12) . . ?
C10 C12 N11 128.7(15) . . ?
C00Q N13 N14 105.2(13) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O001 N2 C00O C9 -178.9(15) . . . . ?
O001 N2 C00O N10 7(3) . . . . ?
O003 N7 C00I N00A -2(2) . . . . ?
O003 N7 C00I C00W 171.5(15) . . . . ?
O007 N7 C00I N00A 180.0(13) . . . . ?
O007 N7 C00I C00W -7(2) . . . . ?
N2 C00O N10 N9 175.6(12) . . . . ?
N00A C00I C00W C00M 2.0(15) . . . . ?
N00A C00I C00W N15 175.1(16) . . . . ?
N00A N4 C00M N6 -172.4(12) . . . . ?
N00A N4 C00M C00W 4(2) . . . . ?
C9 C00O N10 N9 0(2) . . . . ?
C9 C00V N9 N10 -0.4(18) . . . . ?
O00E N3 C10 C00Q -120.9(14) . . . . ?
O00E N3 C10 C12 59.1(17) . . . . ?
O00F N3 C10 C00Q 53.3(18) . . . . ?
O00F N3 C10 C12 -126.7(14) . . . . ?
N8 C9 C00O N2 7(3) . . . . ?
N8 C9 C00O N10 -178.0(17) . . . . ?
N8 C9 C00V N1 -10(3) . . . . ?
N8 C9 C00V N9 178.1(15) . . . . ?
N7 C00I C00W C00M -172.1(14) . . . . ?
N7 C00I C00W N15 1(3) . . . . ?
C00I N00A N4 C00M -2.5(17) . . . . ?
C00I C00W N15 O005 73.3(19) . . . . ?
C00I C00W N15 O17 -106.4(18) . . . . ?
O00J N11 C12 N14 -175.9(8) . . . . ?
O00J N11 C12 C10 0.8(16) . . . . ?
N4 N00A C00I N7 175.1(14) . . . . ?
N4 N00A C00I C00W 0.3(16) . . . . ?
N4 C00M N6 O009 167.4(17) . . . . ?
N4 C00M N6 O14 -5(2) . . . . ?
N4 C00M C00W C00I -3.8(19) . . . . ?
N4 C00M C00W N15 -177.1(16) . . . . ?
N3 C10 C12 N11 3.5(19) . . . . ?
N3 C10 C12 N14 -179.6(9) . . . . ?
C00M C00W N15 O005 -115.2(16) . . . . ?
C00M C00W N15 O17 65(2) . . . . ?
N1 C00V N9 N10 -173.1(12) . . . . ?
C00O C9 N8 O004 -66(2) . . . . ?
C00O C9 N8 O16 112.6(17) . . . . ?
C00O C9 C00V N1 172.6(13) . . . . ?
C00O C9 C00V N9 0.5(19) . . . . ?
C00O N10 N9 C00V 0.2(19) . . . . ?
N6 C00M C00W C00I 172.1(14) . . . . ?
N6 C00M C00W N15 -1(3) . . . . ?
C00Q C10 C12 N11 -176.5(9) . . . . ?
C00Q C10 C12 N14 0.4(13) . . . . ?
O11 N2 C00O C9 -1(3) . . . . ?
O11 N2 C00O N10 -175.2(19) . . . . ?
C10 C00Q N12 O12 10.0(16) . . . . ?
C10 C00Q N12 O13 -172.0(12) . . . . ?
C10 C00Q N13 N14 -0.4(11) . . . . ?
O00U N1 C00V C9 0(2) . . . . ?
O00U N1 C00V N9 171.7(14) . . . . ?
C00V C9 N8 O004 117.0(18) . . . . ?
C00V C9 N8 O16 -64(2) . . . . ?
C00V C9 C00O N2 -175.4(16) . . . . ?
C00V C9 C00O N10 -0.3(19) . . . . ?
C00W C00M N6 O009 -8(2) . . . . ?
C00W C00M N6 O14 179.6(14) . . . . ?
O15 N11 C12 N14 3.7(13) . . . . ?
O15 N11 C12 C10 -179.6(10) . . . . ?
O10 N1 C00V C9 -176.6(16) . . . . ?
O10 N1 C00V N9 -5(2) . . . . ?
N12 C00Q C10 N3 0(2) . . . . ?
N12 C00Q C10 C12 -179.9(9) . . . . ?
N12 C00Q N13 N14 179.5(7) . . . . ?
C12 N14 N13 C00Q 0.7(10) . . . . ?
N13 N14 C12 N11 176.5(8) . . . . ?
N13 N14 C12 C10 -0.7(12) . . . . ?
N13 C00Q C10 N3 180.0(11) . . . . ?
N13 C00Q C10 C12 0.0(13) . . . . ?
N13 C00Q N12 O12 -169.9(9) . . . . ?
N13 C00Q N12 O13 8.1(14) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
