# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry A.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_20230116_2023_0m
_database_code_depnum_ccdc_archive 'CCDC 2281230'
loop_
_audit_author_name
_audit_author_address
'Wen Yujia'
;Xian Modern Chemsitry research institute
China
;
_audit_update_record             
;
2023-07-13 deposited with the CCDC.	2024-02-20 downloaded from the CCDC.
;
_audit_creation_date             2023-01-17
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C9 H8 N6 O9'
_chemical_formula_sum            'C9 H8 N6 O9'
_chemical_formula_weight         344.21
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.960(9)
_cell_length_b                   9.401(10)
_cell_length_c                   18.73(2)
_cell_angle_alpha                88.615(16)
_cell_angle_beta                 88.119(19)
_cell_angle_gamma                63.780(16)
_cell_volume                     1415(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2078
_cell_measurement_temperature    273.15
_cell_measurement_theta_max      23.99
_cell_measurement_theta_min      2.53
_shelx_estimated_absorpt_T_max   0.978
_shelx_estimated_absorpt_T_min   0.957
_exptl_absorpt_coefficient_mu    0.147
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.6769
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0374 before and 0.0309 after correction.
The Ratio of minimum to maximum transmission is 0.9080.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.616
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0205
_diffrn_reflns_av_unetI/netI     0.0432
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            8332
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.756
_diffrn_reflns_theta_min         2.176
_diffrn_ambient_temperature      273.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.982
_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           30.0
_diffrn_source_power             1.2
_diffrn_source_voltage           40.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3713
_reflns_number_total             5923
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40A (Bruker, 2019)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.194
_refine_diff_density_min         -0.179
_refine_diff_density_rms         0.037
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     480
_refine_ls_number_reflns         5923
_refine_ls_number_restraints     139
_refine_ls_R_factor_all          0.0774
_refine_ls_R_factor_gt           0.0437
_refine_ls_restrained_S_all      1.016
_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)+(0.0540P)²+0.1396P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1065
_refine_ls_wR_factor_ref         0.1256
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups
2. Restrained distances
 N0-C029 \\sim N028-C029
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
O018 \\sim O02M \\sim N028 \\sim O0 \\sim N0 \\sim O02N: within 2A with sigma
of 0.01 and sigma for terminal atoms of 0.02 within 2A
O01W \\sim N01N \\sim O01X \\sim O02K \\sim O02J: within 2A with sigma of 0.01
and sigma for terminal atoms of 0.02 within 2A
4. Rigid body (RIGU) restrains
 O0, N0, O02N
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.02
 O018, N028, O02M
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.02
 O01W, N01N, O02J
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.02
 O02K, O01X, N01N
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.02
5. Others
 Sof(O0)=Sof(N0)=Sof(O02N)=1-FVAR(1)
 Sof(O018)=Sof(O02M)=Sof(N028)=FVAR(1)
 Sof(O01X)=Sof(O02K)=1-FVAR(2)
 Sof(O01W)=Sof(O02J)=FVAR(2)
6.a Secondary CH2 refined with riding coordinates:
 C023(H02E,H02F), C02B(H02G,H02H), C02H(H02I,H02J), C02L(H02K,H02L), C01T(H01A,
 H01B), C01Z(H01C,H01D), C02G(H02A,H02B), C02K(H02C,H02D)
;
_atom_sites_solution_hydrogens   geom
_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 -0.07198(15) 0.69827(15) 0.13684(7) 0.0507(3) Uani 1 1 d . . . . .
O007 O 0.35294(17) 0.43136(15) 0.09444(8) 0.0597(4) Uani 1 1 d . . . . .
O00A O 0.1747(2) 0.8162(2) -0.03056(9) 0.0806(5) Uani 1 1 d . . . . .
O00D O 0.4760(3) 0.03309(18) 0.08092(10) 0.0854(5) Uani 1 1 d . . . . .
O00H O -0.2147(2) 0.7747(2) 0.30989(9) 0.0902(6) Uani 1 1 d . . . . .
O00J O -0.5470(2) 0.7158(2) 0.19365(11) 0.0909(6) Uani 1 1 d . . . . .
O00P O -0.3524(2) 0.6355(3) 0.11379(10) 0.0981(6) Uani 1 1 d . . . . .
O00U O 0.7961(2) 0.1123(2) 0.19778(10) 0.0971(6) Uani 1 1 d . . . . .
O024 O 0.6101(3) 0.3529(2) 0.19567(14) 0.1196(8) Uani 1 1 d . . . . .
N00G N -0.4080(2) 0.6873(2) 0.17174(11) 0.0627(5) Uani 1 1 d . . . . .
N00V N 0.6647(3) 0.2157(3) 0.17918(11) 0.0729(6) Uani 1 1 d . . . . .
N011 N 0.3677(3) 0.1885(2) 0.06241(11) 0.0709(5) Uani 1 1 d . . . . .
N01G N 0.5945(3) 0.0287(2) 0.12553(11) 0.0777(6) Uani 1 1 d . . . . .
N01H N -0.0947(2) 0.7593(2) 0.25710(10) 0.0709(5) Uani 1 1 d . . . . .
N01K N -0.3401(3) 0.7499(2) 0.28343(10) 0.0739(6) Uani 1 1 d . . . . .
C019 C 0.4202(3) 0.2751(2) 0.09626(11) 0.0532(5) Uani 1 1 d . . . . .
C01D C -0.1475(2) 0.7231(2) 0.20014(10) 0.0500(5) Uani 1 1 d . . . . .
C01I C 0.1459(2) 0.6833(2) 0.05802(10) 0.0476(5) Uani 1 1 d . . . . .
C01P C -0.2998(2) 0.7184(2) 0.21732(11) 0.0512(5) Uani 1 1 d . . . . .
C023 C 0.2122(3) 0.5074(2) 0.04806(11) 0.0548(5) Uani 1 1 d . . . . .
H02E H 0.127041 0.473369 0.060681 0.066 Uiso 1 1 calc R U . . .
H02F H 0.246925 0.479992 -0.001341 0.066 Uiso 1 1 calc R U . . .
C027 C 0.5621(3) 0.1744(2) 0.13481(12) 0.0582(6) Uani 1 1 d . . . . .
C02B C 0.0707(2) 0.7330(2) 0.13113(11) 0.0540(5) Uani 1 1 d . . . . .
H02G H 0.150734 0.674676 0.167311 0.065 Uiso 1 1 calc R U . . .
H02H H 0.035996 0.845439 0.137458 0.065 Uiso 1 1 calc R U . . .
C02H C 0.0433(3) 0.7783(3) -0.00561(12) 0.0660(6) Uani 1 1 d . . . . .
H02I H 0.018841 0.713995 -0.038679 0.079 Uiso 1 1 calc R U . . .
H02J H -0.057547 0.870540 0.008448 0.079 Uiso 1 1 calc R U . . .
C02L C 0.2670(3) 0.7503(3) 0.03285(13) 0.0675(6) Uani 1 1 d . . . . .
H02K H 0.268502 0.829790 0.064506 0.081 Uiso 1 1 calc R U . . .
H02L H 0.378993 0.669014 0.023246 0.081 Uiso 1 1 calc R U . . .
O003 O 0.58522(16) 0.22739(17) 0.50822(7) 0.0536(4) Uani 1 1 d . . . . .
O004 O 0.88132(16) 0.03161(15) 0.65607(7) 0.0522(4) Uani 1 1 d . . . . .
O009 O 1.1490(2) -0.35603(19) 0.62294(10) 0.0819(5) Uani 1 1 d . . . . .
O00L O 0.2374(2) 0.1690(2) 0.49473(10) 0.0843(5) Uani 1 1 d . . . . .
O00N O 0.7221(3) 0.5107(2) 0.61199(10) 0.0938(6) Uani 1 1 d . . . . .
O018 O 0.807(2) -0.0839(19) 0.7914(10) 0.089(3) Uani 0.63(4) 1 d . U P A 1
O01W O 0.429(3) 0.167(2) 0.2995(12) 0.107(4) Uani 0.63(3) 1 d . U P B 1
O02J O 0.6498(12) 0.1344(19) 0.3594(5) 0.094(3) Uani 0.63(3) 1 d . U P B 1
O02M O 0.949(3) -0.3264(13) 0.8164(5) 0.115(3) Uani 0.63(4) 1 d . U P A 1
N00Q N 1.0769(2) -0.1965(2) 0.60129(10) 0.0599(5) Uani 1 1 d . . . . .
N017 N 0.3449(2) 0.2021(2) 0.53574(10) 0.0681(5) Uani 1 1 d . . . . .
N01M N 0.2870(2) 0.1503(2) 0.42476(12) 0.0701(5) Uani 1 1 d . . . . .
N01N N 0.5045(3) 0.1605(3) 0.35477(11) 0.0770(6) Uani 1 1 d . U . . .
N01Y N 1.0918(3) -0.3751(2) 0.68880(11) 0.0787(6) Uani 1 1 d . . . . .
N028 N 0.903(4) -0.218(2) 0.7763(9) 0.080(3) Uani 0.63(4) 1 d D U P A 1
C014 C 0.4574(2) 0.2025(2) 0.49094(11) 0.0475(5) Uani 1 1 d . . . . .
C016 C 0.7431(2) 0.2799(2) 0.59565(10) 0.0468(5) Uani 1 1 d . . . . .
C01O C 0.9787(2) -0.1221(2) 0.65409(11) 0.0480(5) Uani 1 1 d . . . . .
C01T C 0.8939(2) 0.1218(2) 0.59397(11) 0.0521(5) Uani 1 1 d . . . . .
H01A H 0.897420 0.066325 0.550481 0.063 Uiso 1 1 calc R U . . .
H01B H 0.994521 0.136125 0.595552 0.063 Uiso 1 1 calc R U . . .
C01Z C 0.5846(2) 0.2680(2) 0.58316(10) 0.0515(5) Uani 1 1 d . . . . .
H01C H 0.577344 0.186885 0.614044 0.062 Uiso 1 1 calc R U . . .
H01D H 0.489531 0.368317 0.593607 0.062 Uiso 1 1 calc R U . . .
C021 C 0.4188(3) 0.1710(2) 0.42205(11) 0.0518(5) Uani 1 1 d . . . . .
C029 C 0.9901(3) -0.2346(2) 0.70786(11) 0.0580(5) Uani 1 1 d D . . . .
C02G C 0.7627(3) 0.4102(2) 0.55123(12) 0.0615(6) Uani 1 1 d . . . . .
H02A H 0.875086 0.378619 0.532620 0.074 Uiso 1 1 calc R U . . .
H02B H 0.682924 0.453382 0.513402 0.074 Uiso 1 1 calc R U . . .
C02K C 0.7231(3) 0.3878(3) 0.65916(11) 0.0640(6) Uani 1 1 d . . . . .
H02C H 0.619467 0.417638 0.686062 0.077 Uiso 1 1 calc R U . . .
H02D H 0.817041 0.345843 0.690692 0.077 Uiso 1 1 calc R U . . .
O0 O 0.844(4) -0.064(3) 0.7990(17) 0.086(4) Uani 0.37(4) 1 d . U P A 2
N0 N 0.908(7) -0.196(5) 0.7770(16) 0.084(4) Uani 0.37(4) 1 d D U P A 2
O02N O 0.883(4) -0.328(2) 0.8001(15) 0.112(5) Uani 0.37(4) 1 d . U P A 2
O01X O 0.456(4) 0.127(3) 0.304(2) 0.087(4) Uani 0.37(3) 1 d . U P B 2
O02K O 0.6050(19) 0.226(3) 0.3523(6) 0.101(3) Uani 0.37(3) 1 d . U P B 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O001 C01D 1.319(2) . ?
O001 C02B 1.453(3) . ?
O007 C019 1.319(3) . ?
O007 C023 1.449(3) . ?
O00A C02H 1.435(3) . ?
O00A C02L 1.434(3) . ?
O00D N011 1.394(3) . ?
O00D N01G 1.358(3) . ?
O00H N01H 1.398(3) . ?
O00H N01K 1.356(3) . ?
O00J N00G 1.212(2) . ?
O00P N00G 1.200(3) . ?
O00U N00V 1.205(3) . ?
O024 N00V 1.204(3) . ?
N00G C01P 1.438(3) . ?
N00V C027 1.438(3) . ?
N011 C019 1.291(3) . ?
N01G C027 1.284(3) . ?
N01H C01D 1.293(3) . ?
N01K C01P 1.283(3) . ?
C019 C027 1.413(3) . ?
C01D C01P 1.411(3) . ?
C01I C023 1.504(3) . ?
C01I C02B 1.497(3) . ?
C01I C02H 1.536(3) . ?
C01I C02L 1.533(3) . ?
C023 H02E 0.9700 . ?
C023 H02F 0.9700 . ?
C02B H02G 0.9700 . ?
C02B H02H 0.9700 . ?
C02H H02I 0.9700 . ?
C02H H02J 0.9700 . ?
C02L H02K 0.9700 . ?
C02L H02L 0.9700 . ?
O003 C014 1.318(3) . ?
O003 C01Z 1.463(3) . ?
O004 C01O 1.318(3) . ?
O004 C01T 1.454(3) . ?
O009 N00Q 1.401(3) . ?
O009 N01Y 1.359(3) . ?
O00L N017 1.393(3) . ?
O00L N01M 1.360(3) . ?
O00N C02G 1.428(3) . ?
O00N C02K 1.434(3) . ?
O018 N028 1.21(2) . ?
O01W N01N 1.24(2) . ?
O02J N01N 1.220(8) . ?
O02M N028 1.18(2) . ?
N00Q C01O 1.294(3) . ?
N017 C014 1.291(3) . ?
N01M C021 1.278(3) . ?
N01N C021 1.436(3) . ?
N01N O01X 1.17(3) . ?
N01N O02K 1.293(16) . ?
N01Y C029 1.281(3) . ?
N028 C029 1.454(8) . ?
C014 C021 1.418(3) . ?
C016 C01T 1.504(3) . ?
C016 C01Z 1.499(3) . ?
C016 C02G 1.535(3) . ?
C016 C02K 1.536(3) . ?
C01O C029 1.415(3) . ?
C01T H01A 0.9700 . ?
C01T H01B 0.9700 . ?
C01Z H01C 0.9700 . ?
C01Z H01D 0.9700 . ?
C029 N0 1.440(14) . ?
C02G H02A 0.9700 . ?
C02G H02B 0.9700 . ?
C02K H02C 0.9700 . ?
C02K H02D 0.9700 . ?
O0 N0 1.19(4) . ?
N0 O02N 1.41(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
C01D O001 C02B 115.35(16) . . ?
C019 O007 C023 115.33(17) . . ?
C02L O00A C02H 91.55(16) . . ?
N01G O00D N011 111.26(18) . . ?
N01K O00H N01H 111.59(17) . . ?
O00J N00G C01P 118.7(2) . . ?
O00P N00G O00J 124.8(2) . . ?
O00P N00G C01P 116.45(19) . . ?
O00U N00V C027 118.5(2) . . ?
O024 N00V O00U 125.0(3) . . ?
O024 N00V C027 116.5(2) . . ?
C019 N011 O00D 104.7(2) . . ?
C027 N01G O00D 105.1(2) . . ?
C01D N01H O00H 104.5(2) . . ?
C01P N01K O00H 104.56(18) . . ?
O007 C019 C027 125.9(2) . . ?
N011 C019 O007 125.4(2) . . ?
N011 C019 C027 108.7(2) . . ?
O001 C01D C01P 126.50(19) . . ?
N01H C01D O001 125.2(2) . . ?
N01H C01D C01P 108.32(19) . . ?
C023 C01I C02H 112.07(18) . . ?
C023 C01I C02L 113.96(18) . . ?
C02B C01I C023 111.89(16) . . ?
C02B C01I C02H 117.17(18) . . ?
C02B C01I C02L 115.05(18) . . ?
C02L C01I C02H 84.11(17) . . ?
N01K C01P N00G 119.8(2) . . ?
N01K C01P C01D 111.0(2) . . ?
C01D C01P N00G 129.17(19) . . ?
O007 C023 C01I 107.01(17) . . ?
O007 C023 H02E 110.3 . . ?
O007 C023 H02F 110.3 . . ?
C01I C023 H02E 110.3 . . ?
C01I C023 H02F 110.3 . . ?
H02E C023 H02F 108.6 . . ?
N01G C027 N00V 120.7(2) . . ?
N01G C027 C019 110.3(2) . . ?
C019 C027 N00V 129.0(2) . . ?
O001 C02B C01I 106.56(16) . . ?
O001 C02B H02G 110.4 . . ?
O001 C02B H02H 110.4 . . ?
C01I C02B H02G 110.4 . . ?
C01I C02B H02H 110.4 . . ?
H02G C02B H02H 108.6 . . ?
O00A C02H C01I 91.56(18) . . ?
O00A C02H H02I 113.4 . . ?
O00A C02H H02J 113.4 . . ?
C01I C02H H02I 113.4 . . ?
C01I C02H H02J 113.4 . . ?
H02I C02H H02J 110.7 . . ?
O00A C02L C01I 91.71(17) . . ?
O00A C02L H02K 113.3 . . ?
O00A C02L H02L 113.3 . . ?
C01I C02L H02K 113.3 . . ?
C01I C02L H02L 113.3 . . ?
H02K C02L H02L 110.7 . . ?
C014 O003 C01Z 114.32(15) . . ?
C01O O004 C01T 115.42(16) . . ?
N01Y O009 N00Q 111.57(15) . . ?
N01M O00L N017 111.36(16) . . ?
C02G O00N C02K 92.22(17) . . ?
C01O N00Q O009 104.51(17) . . ?
C014 N017 O00L 104.8(2) . . ?
C021 N01M O00L 104.87(18) . . ?
O01W N01N C021 117.7(10) . . ?
O02J N01N O01W 127.4(11) . . ?
O02J N01N C021 114.6(4) . . ?
O01X N01N C021 119.4(17) . . ?
O01X N01N O02K 122.9(18) . . ?
O02K N01N C021 115.6(7) . . ?
C029 N01Y O009 104.58(19) . . ?
O018 N028 C029 114.7(15) . . ?
O02M N028 O018 124.8(12) . . ?
O02M N028 C029 119.2(15) . . ?
O003 C014 C021 127.24(18) . . ?
N017 C014 O003 124.5(2) . . ?
N017 C014 C021 108.3(2) . . ?
C01T C016 C02G 114.28(18) . . ?
C01T C016 C02K 117.15(18) . . ?
C01Z C016 C01T 112.98(18) . . ?
C01Z C016 C02G 114.04(17) . . ?
C01Z C016 C02K 111.08(17) . . ?
C02G C016 C02K 84.40(17) . . ?
O004 C01O C029 126.19(19) . . ?
N00Q C01O O004 125.49(18) . . ?
N00Q C01O C029 108.29(19) . . ?
O004 C01T C016 107.30(16) . . ?
O004 C01T H01A 110.3 . . ?
O004 C01T H01B 110.3 . . ?
C016 C01T H01A 110.3 . . ?
C016 C01T H01B 110.3 . . ?
H01A C01T H01B 108.5 . . ?
O003 C01Z C016 107.90(15) . . ?
O003 C01Z H01C 110.1 . . ?
O003 C01Z H01D 110.1 . . ?
C016 C01Z H01C 110.1 . . ?
C016 C01Z H01D 110.1 . . ?
H01C C01Z H01D 108.4 . . ?
N01M C021 N01N 119.7(2) . . ?
N01M C021 C014 110.7(2) . . ?
C014 C021 N01N 129.6(2) . . ?
N01Y C029 N028 117.1(9) . . ?
N01Y C029 C01O 111.1(2) . . ?
N01Y C029 N0 124.0(17) . . ?
C01O C029 N028 131.7(8) . . ?
C01O C029 N0 124.8(17) . . ?
O00N C02G C016 91.39(18) . . ?
O00N C02G H02A 113.4 . . ?
O00N C02G H02B 113.4 . . ?
C016 C02G H02A 113.4 . . ?
C016 C02G H02B 113.4 . . ?
H02A C02G H02B 110.7 . . ?
O00N C02K C016 91.12(18) . . ?
O00N C02K H02C 113.4 . . ?
O00N C02K H02D 113.4 . . ?
C016 C02K H02C 113.4 . . ?
C016 C02K H02D 113.4 . . ?
H02C C02K H02D 110.7 . . ?
O0 N0 C029 122(3) . . ?
O0 N0 O02N 129(2) . . ?
O02N N0 C029 107(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 C01D C01P N00G -0.4(3) . . . . ?
O001 C01D C01P N01K -179.18(18) . . . . ?
O007 C019 C027 N00V -0.6(3) . . . . ?
O007 C019 C027 N01G 179.66(19) . . . . ?
O00D N011 C019 O007 -179.64(18) . . . . ?
O00D N011 C019 C027 0.9(2) . . . . ?
O00D N01G C027 N00V -179.35(19) . . . . ?
O00D N01G C027 C019 0.4(2) . . . . ?
O00H N01H C01D O001 179.61(18) . . . . ?
O00H N01H C01D C01P 0.8(2) . . . . ?
O00H N01K C01P N00G -179.10(18) . . . . ?
O00H N01K C01P C01D -0.2(2) . . . . ?
O00J N00G C01P N01K 11.5(3) . . . . ?
O00J N00G C01P C01D -167.2(2) . . . . ?
O00P N00G C01P N01K -169.1(2) . . . . ?
O00P N00G C01P C01D 12.3(3) . . . . ?
O00U N00V C027 N01G 12.1(3) . . . . ?
O00U N00V C027 C019 -167.6(2) . . . . ?
O024 N00V C027 N01G -167.0(2) . . . . ?
O024 N00V C027 C019 13.3(4) . . . . ?
N011 O00D N01G C027 0.2(2) . . . . ?
N011 C019 C027 N00V 178.8(2) . . . . ?
N011 C019 C027 N01G -0.9(2) . . . . ?
N01G O00D N011 C019 -0.7(2) . . . . ?
N01H O00H N01K C01P 0.8(2) . . . . ?
N01H C01D C01P N00G 178.3(2) . . . . ?
N01H C01D C01P N01K -0.4(2) . . . . ?
N01K O00H N01H C01D -1.0(2) . . . . ?
C019 O007 C023 C01I 175.57(16) . . . . ?
C01D O001 C02B C01I 175.02(15) . . . . ?
C023 O007 C019 N011 -2.2(3) . . . . ?
C023 O007 C019 C027 177.13(18) . . . . ?
C023 C01I C02B O001 -64.1(2) . . . . ?
C023 C01I C02H O00A -105.90(19) . . . . ?
C023 C01I C02L O00A 104.0(2) . . . . ?
C02B O001 C01D N01H -7.3(3) . . . . ?
C02B O001 C01D C01P 171.32(18) . . . . ?
C02B C01I C023 O007 -67.4(2) . . . . ?
C02B C01I C02H O00A 122.8(2) . . . . ?
C02B C01I C02L O00A -124.89(19) . . . . ?
C02H O00A C02L C01I 8.10(18) . . . . ?
C02H C01I C023 O007 158.64(16) . . . . ?
C02H C01I C02B O001 67.3(2) . . . . ?
C02H C01I C02L O00A -7.61(17) . . . . ?
C02L O00A C02H C01I -8.09(18) . . . . ?
C02L C01I C023 O007 65.3(2) . . . . ?
C02L C01I C02B O001 163.76(16) . . . . ?
C02L C01I C02H O00A 7.60(17) . . . . ?
O003 C014 C021 N01M 178.98(19) . . . . ?
O003 C014 C021 N01N -0.9(4) . . . . ?
O004 C01O C029 N01Y 177.7(2) . . . . ?
O004 C01O C029 N028 1(2) . . . . ?
O004 C01O C029 N0 -6(3) . . . . ?
O009 N00Q C01O O004 -178.07(18) . . . . ?
O009 N00Q C01O C029 0.0(2) . . . . ?
O009 N01Y C029 N028 177.6(16) . . . . ?
O009 N01Y C029 C01O 0.6(3) . . . . ?
O009 N01Y C029 N0 -175(3) . . . . ?
O00L N017 C014 O003 -179.14(17) . . . . ?
O00L N017 C014 C021 0.5(2) . . . . ?
O00L N01M C021 N01N -179.59(19) . . . . ?
O00L N01M C021 C014 0.5(2) . . . . ?
O018 N028 C029 N01Y -179(2) . . . . ?
O018 N028 C029 C01O -3(4) . . . . ?
O01W N01N C021 N01M 15.8(11) . . . . ?
O01W N01N C021 C014 -164.2(10) . . . . ?
O02J N01N C021 N01M -159.1(8) . . . . ?
O02J N01N C021 C014 20.8(9) . . . . ?
O02M N028 C029 N01Y 13(4) . . . . ?
O02M N028 C029 C01O -170(2) . . . . ?
N00Q O009 N01Y C029 -0.6(3) . . . . ?
N00Q C01O C029 N01Y -0.4(3) . . . . ?
N00Q C01O C029 N028 -176.9(19) . . . . ?
N00Q C01O C029 N0 176(3) . . . . ?
N017 O00L N01M C021 -0.2(2) . . . . ?
N017 C014 C021 N01M -0.7(3) . . . . ?
N017 C014 C021 N01N 179.4(2) . . . . ?
N01M O00L N017 C014 -0.3(2) . . . . ?
N01Y O009 N00Q C01O 0.3(2) . . . . ?
N01Y C029 N0 O0 163(4) . . . . ?
N01Y C029 N0 O02N -32(5) . . . . ?
C014 O003 C01Z C016 175.61(15) . . . . ?
C01O O004 C01T C016 163.58(16) . . . . ?
C01O C029 N0 O0 -12(7) . . . . ?
C01O C029 N0 O02N 153(2) . . . . ?
C01T O004 C01O N00Q -2.6(3) . . . . ?
C01T O004 C01O C029 179.62(19) . . . . ?
C01T C016 C01Z O003 -70.6(2) . . . . ?
C01T C016 C02G O00N -124.10(19) . . . . ?
C01T C016 C02K O00N 121.2(2) . . . . ?
C01Z O003 C014 N017 -4.6(3) . . . . ?
C01Z O003 C014 C021 175.81(19) . . . . ?
C01Z C016 C01T O004 -67.9(2) . . . . ?
C01Z C016 C02G O00N 103.83(19) . . . . ?
C01Z C016 C02K O00N -106.88(19) . . . . ?
C02G O00N C02K C016 -7.23(18) . . . . ?
C02G C016 C01T O004 159.55(16) . . . . ?
C02G C016 C01Z O003 62.1(2) . . . . ?
C02G C016 C02K O00N 6.76(17) . . . . ?
C02K O00N C02G C016 7.24(18) . . . . ?
C02K C016 C01T O004 63.2(2) . . . . ?
C02K C016 C01Z O003 155.40(16) . . . . ?
C02K C016 C02G O00N -6.79(17) . . . . ?
O01X N01N C021 N01M -2.7(16) . . . . ?
O01X N01N C021 C014 177.2(16) . . . . ?
O02K N01N C021 N01M 161.1(12) . . . . ?
O02K N01N C021 C014 -19.0(12) . . . . ?

_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_dqd_20230403_wenyujia_0m
_database_code_depnum_ccdc_archive 'CCDC 2281330'
loop_
_audit_author_name
_audit_author_address
'Wen Yujia'
;Xian modern chemistry research institute
China
;
_audit_update_record             
;
2023-07-13 deposited with the CCDC.	2024-02-20 downloaded from the CCDC.
;
_audit_creation_date             2023-04-10
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C7 H8 Br N3 O5'
_chemical_formula_sum            'C7 H8 Br N3 O5'
_chemical_formula_weight         294.07
_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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   5.763
_cell_length_b                   18.197
_cell_length_c                   19.747
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2071.0
_cell_formula_units_Z            8
_cell_measurement_reflns_used    1751
_cell_measurement_temperature    273.15
_cell_measurement_theta_max      19.01
_cell_measurement_theta_min      2.45
_shelx_estimated_absorpt_T_max   0.503
_shelx_estimated_absorpt_T_min   0.503
_exptl_absorpt_coefficient_mu    3.981
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6532
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0750 before and 0.0573 after correction.
The Ratio of minimum to maximum transmission is 0.8760.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.886
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1168
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1028
_diffrn_reflns_av_unetI/netI     0.0693
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            20642
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.318
_diffrn_reflns_theta_min         2.063
_diffrn_ambient_temperature      273.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.996
_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           35.0
_diffrn_source_power             1.575
_diffrn_source_voltage           45.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1371
_reflns_number_total             2576
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40A (Bruker, 2019)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.301
_refine_diff_density_min         -0.471
_refine_diff_density_rms         0.083
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.996
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         2576
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1158
_refine_ls_R_factor_gt           0.0432
_refine_ls_restrained_S_all      0.996
_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)+(0.0288P)²+1.7534P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0752
_refine_ls_wR_factor_ref         0.0947
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C00D(H00A,H00B), C00E(H00C,H00D), C00F(H00E,H00F), C00G(H00G,H00H)
;
_atom_sites_solution_hydrogens   geom
_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
Br01 Br 0.89632(8) 0.06393(2) 0.69184(2) 0.05488(17) Uani 1 1 d . . . . .
O002 O 0.4854(4) 0.26604(13) 0.62920(13) 0.0436(7) Uani 1 1 d . . . . .
O003 O 0.6889(4) 0.18137(14) 0.49908(12) 0.0440(7) Uani 1 1 d . . . . .
O004 O 0.5975(5) 0.40662(16) 0.57589(16) 0.0575(8) Uani 1 1 d . . . . .
O005 O 0.3009(5) 0.47725(16) 0.56243(15) 0.0602(9) Uani 1 1 d . . . . .
N006 N 0.3998(7) 0.42465(17) 0.58659(16) 0.0419(8) Uani 1 1 d . . . . .
O007 O 0.0209(5) 0.34858(17) 0.70305(16) 0.0645(9) Uani 1 1 d . . . . .
N008 N 0.1596(6) 0.28612(18) 0.69573(17) 0.0483(9) Uani 1 1 d . . . . .
C009 C 0.6130(6) 0.14662(18) 0.59997(17) 0.0292(8) Uani 1 1 d . . . . .
C00A C 0.3154(7) 0.3062(2) 0.65248(18) 0.0339(9) Uani 1 1 d . . . . .
N00B N 0.0947(6) 0.4048(2) 0.66367(19) 0.0554(10) Uani 1 1 d . . . . .
C00C C 0.2728(6) 0.3794(2) 0.63326(18) 0.0339(9) Uani 1 1 d . . . . .
C00D C 0.8168(6) 0.1802(2) 0.56185(18) 0.0380(9) Uani 1 1 d . . . . .
H00A H 0.858651 0.228753 0.577951 0.046 Uiso 1 1 calc R U . . .
H00B H 0.951989 0.148450 0.560453 0.046 Uiso 1 1 calc R U . . .
C00E C 0.6547(6) 0.0693(2) 0.62361(19) 0.0397(10) Uani 1 1 d . . . . .
H00C H 0.698408 0.039146 0.585173 0.048 Uiso 1 1 calc R U . . .
H00D H 0.511809 0.049588 0.642171 0.048 Uiso 1 1 calc R U . . .
C00F C 0.5031(7) 0.19166(18) 0.65436(19) 0.0404(10) Uani 1 1 d . . . . .
H00E H 0.350344 0.172574 0.665111 0.049 Uiso 1 1 calc R U . . .
H00F H 0.597220 0.190411 0.695064 0.049 Uiso 1 1 calc R U . . .
C00G C 0.4900(7) 0.1496(2) 0.53142(19) 0.0404(9) Uani 1 1 d . . . . .
H00G H 0.450098 0.101430 0.513853 0.048 Uiso 1 1 calc R U . . .
H00H H 0.355528 0.181612 0.531236 0.048 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br01 C00E 1.940(3) . ?
O002 C00A 1.306(4) . ?
O002 C00F 1.446(4) . ?
O003 C00D 1.442(4) . ?
O003 C00G 1.434(4) . ?
O004 N006 1.204(4) . ?
O005 N006 1.212(4) . ?
N006 C00C 1.437(5) . ?
O007 N008 1.397(4) . ?
O007 N00B 1.354(4) . ?
N008 C00A 1.292(4) . ?
C009 C00D 1.523(5) . ?
C009 C00E 1.502(5) . ?
C009 C00F 1.492(5) . ?
C009 C00G 1.529(5) . ?
C00A C00C 1.406(5) . ?
N00B C00C 1.276(4) . ?
C00D H00A 0.9700 . ?
C00D H00B 0.9700 . ?
C00E H00C 0.9700 . ?
C00E H00D 0.9700 . ?
C00F H00E 0.9700 . ?
C00F H00F 0.9700 . ?
C00G H00G 0.9700 . ?
C00G H00H 0.9700 . ?

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
C00A O002 C00F 117.1(3) . . ?
C00G O003 C00D 91.1(2) . . ?
O004 N006 O005 126.2(4) . . ?
O004 N006 C00C 116.0(3) . . ?
O005 N006 C00C 117.8(4) . . ?
N00B O007 N008 112.1(3) . . ?
C00A N008 O007 103.7(3) . . ?
C00D C009 C00G 84.6(3) . . ?
C00E C009 C00D 113.9(3) . . ?
C00E C009 C00G 112.5(3) . . ?
C00F C009 C00D 117.6(3) . . ?
C00F C009 C00E 111.0(3) . . ?
C00F C009 C00G 114.9(3) . . ?
O002 C00A C00C 124.4(3) . . ?
N008 C00A O002 126.6(3) . . ?
N008 C00A C00C 108.9(3) . . ?
C00C N00B O007 104.4(3) . . ?
C00A C00C N006 128.8(4) . . ?
N00B C00C N006 120.2(4) . . ?
N00B C00C C00A 111.0(4) . . ?
O003 C00D C009 92.1(3) . . ?
O003 C00D H00A 113.3 . . ?
O003 C00D H00B 113.3 . . ?
C009 C00D H00A 113.3 . . ?
C009 C00D H00B 113.3 . . ?
H00A C00D H00B 110.6 . . ?
Br01 C00E H00C 109.2 . . ?
Br01 C00E H00D 109.2 . . ?
C009 C00E Br01 112.2(2) . . ?
C009 C00E H00C 109.2 . . ?
C009 C00E H00D 109.2 . . ?
H00C C00E H00D 107.9 . . ?
O002 C00F C009 107.3(3) . . ?
O002 C00F H00E 110.3 . . ?
O002 C00F H00F 110.3 . . ?
C009 C00F H00E 110.3 . . ?
C009 C00F H00F 110.3 . . ?
H00E C00F H00F 108.5 . . ?
O003 C00G C009 92.2(3) . . ?
O003 C00G H00G 113.3 . . ?
O003 C00G H00H 113.3 . . ?
C009 C00G H00G 113.3 . . ?
C009 C00G H00H 113.3 . . ?
H00G C00G H00H 110.6 . . ?

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
O002 C00A C00C N006 -0.5(6) . . . . ?
O002 C00A C00C N00B 179.6(3) . . . . ?
O004 N006 C00C C00A -21.6(6) . . . . ?
O004 N006 C00C N00B 158.3(4) . . . . ?
O005 N006 C00C C00A 159.2(4) . . . . ?
O005 N006 C00C N00B -20.9(5) . . . . ?
O007 N008 C00A O002 -179.9(3) . . . . ?
O007 N008 C00A C00C -0.3(4) . . . . ?
O007 N00B C00C N006 -179.7(3) . . . . ?
O007 N00B C00C C00A 0.2(4) . . . . ?
N008 O007 N00B C00C -0.4(5) . . . . ?
N008 C00A C00C N006 180.0(4) . . . . ?
N008 C00A C00C N00B 0.1(5) . . . . ?
C00A O002 C00F C009 151.1(3) . . . . ?
N00B O007 N008 C00A 0.5(4) . . . . ?
C00D O003 C00G C009 0.2(3) . . . . ?
C00D C009 C00E Br01 66.0(3) . . . . ?
C00D C009 C00F O002 42.1(4) . . . . ?
C00D C009 C00G O003 -0.2(3) . . . . ?
C00E C009 C00D O003 112.4(3) . . . . ?
C00E C009 C00F O002 175.8(3) . . . . ?
C00E C009 C00G O003 -113.9(3) . . . . ?
C00F O002 C00A N008 -0.3(6) . . . . ?
C00F O002 C00A C00C -179.8(3) . . . . ?
C00F C009 C00D O003 -115.2(3) . . . . ?
C00F C009 C00E Br01 -69.5(3) . . . . ?
C00F C009 C00G O003 117.8(3) . . . . ?
C00G O003 C00D C009 -0.2(3) . . . . ?
C00G C009 C00D O003 0.2(3) . . . . ?
C00G C009 C00E Br01 160.2(3) . . . . ?
C00G C009 C00F O002 -55.1(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_2fn3_20230703_0m
_database_code_depnum_ccdc_archive 'CCDC 2281231'
loop_
_audit_author_name
_audit_author_address
'Wen Yujia'
;Xian Modern Chemsitry research institute
China
;
_audit_update_record             
;
2023-07-25 deposited with the CCDC.	2024-02-20 downloaded from the CCDC.
;
_audit_creation_date             2023-07-22
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C9 H8 N10 O5'
_chemical_formula_sum            'C9 H8 N10 O5'
_chemical_formula_weight         336.25
_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                   14.2832(19)
_cell_length_b                   7.5634(9)
_cell_length_c                   13.8345(18)
_cell_angle_alpha                90
_cell_angle_beta                 105.893(6)
_cell_angle_gamma                90
_cell_volume                     1437.4(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2923
_cell_measurement_temperature    273.15
_cell_measurement_theta_max      23.688
_cell_measurement_theta_min      2.966
_shelx_estimated_absorpt_T_max   0.962
_shelx_estimated_absorpt_T_min   0.938
_exptl_absorpt_coefficient_mu    0.130
_exptl_absorpt_correction_T_max  0.7470
_exptl_absorpt_correction_T_min  0.6923
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0624 before and 0.0552 after correction.
The Ratio of minimum to maximum transmission is 0.9268.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.554
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             688
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.3
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0854
_diffrn_reflns_av_unetI/netI     0.0617
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            34439
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         35.650
_diffrn_reflns_theta_min         1.482
_diffrn_ambient_temperature      273.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           35.0
_diffrn_source_power             1.575
_diffrn_source_voltage           45.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2787
_reflns_number_total             6640
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40A (Bruker, 2019)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.184
_refine_diff_density_min         -0.232
_refine_diff_density_rms         0.055
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.997
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         6640
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1434
_refine_ls_R_factor_gt           0.0487
_refine_ls_restrained_S_all      0.997
_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)+(0.0438P)²+0.1573P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0996
_refine_ls_wR_factor_ref         0.1358
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B), C4(H4A,H4B), C2(H2A,H2B), C1(H1A,H1B)
;
_atom_sites_solution_hydrogens   geom
_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
O2 O 0.84334(6) 0.10367(12) 0.60912(7) 0.0432(2) Uani 1 1 d . . . . .
O3 O 0.66282(6) -0.02949(15) 0.39319(7) 0.0519(3) Uani 1 1 d . . . . .
O1 O 0.76854(8) -0.43502(13) 0.57916(8) 0.0558(3) Uani 1 1 d . . . . .
O5 O 1.02098(9) 0.40909(16) 0.60937(10) 0.0707(3) Uani 1 1 d . . . . .
O4 O 0.42357(7) 0.07153(18) 0.28033(9) 0.0704(3) Uani 1 1 d . . . . .
N9 N 0.59586(9) 0.11668(17) 0.09379(10) 0.0554(3) Uani 1 1 d . . . . .
N1 N 0.96543(10) 0.26330(17) 0.56508(10) 0.0584(3) Uani 1 1 d . . . . .
N2 N 0.99756(10) 0.46066(16) 0.69597(11) 0.0588(3) Uani 1 1 d . . . . .
N6 N 0.49565(9) 0.01777(19) 0.36595(10) 0.0565(3) Uani 1 1 d . . . . .
N8 N 0.62501(9) 0.0718(2) 0.18391(10) 0.0624(4) Uani 1 1 d . . . . .
N7 N 0.46250(9) 0.09948(19) 0.20000(10) 0.0597(3) Uani 1 1 d . . . . .
N10 N 0.58169(12) 0.1533(2) 0.01317(12) 0.0770(4) Uani 1 1 d . . . . .
C6 C 0.91042(9) 0.23049(17) 0.62280(10) 0.0404(3) Uani 1 1 d . . . . .
C5 C 0.85099(9) -0.03378(17) 0.53854(10) 0.0407(3) Uani 1 1 d . . . . .
H5A H 0.913967 -0.091361 0.560162 0.049 Uiso 1 1 calc R U . . .
H5B H 0.843492 0.016089 0.472252 0.049 Uiso 1 1 calc R U . . .
C3 C 0.77075(8) -0.16421(16) 0.53625(9) 0.0372(3) Uani 1 1 d . . . . .
C8 C 0.57440(9) 0.01524(18) 0.33760(10) 0.0431(3) Uani 1 1 d . . . . .
C7 C 0.93050(9) 0.35214(17) 0.70453(10) 0.0422(3) Uani 1 1 d . . . . .
C9 C 0.55398(10) 0.06539(18) 0.23523(11) 0.0458(3) Uani 1 1 d . . . . .
C4 C 0.67011(9) -0.08750(19) 0.49483(10) 0.0440(3) Uani 1 1 d . . . . .
H4A H 0.621038 -0.176239 0.494654 0.053 Uiso 1 1 calc R U . . .
H4B H 0.660518 0.011502 0.535655 0.053 Uiso 1 1 calc R U . . .
C2 C 0.77823(10) -0.26949(18) 0.63287(10) 0.0457(3) Uani 1 1 d . . . . .
H2A H 0.840501 -0.256100 0.682702 0.055 Uiso 1 1 calc R U . . .
H2B H 0.725116 -0.246424 0.662300 0.055 Uiso 1 1 calc R U . . .
C1 C 0.78149(10) -0.34641(18) 0.49143(11) 0.0488(3) Uani 1 1 d . . . . .
H1A H 0.730451 -0.372291 0.430657 0.059 Uiso 1 1 calc R U . . .
H1B H 0.845148 -0.365742 0.480999 0.059 Uiso 1 1 calc R U . . .
N4 N 0.83488(10) 0.25171(18) 0.79615(9) 0.0556(3) Uani 1 1 d . . . . .
N3 N 0.89166(11) 0.37042(17) 0.78504(10) 0.0604(3) Uani 1 1 d . . . . .
N5 N 0.78338(12) 0.1600(2) 0.81771(13) 0.0812(5) 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
O2 C6 1.3321(15) . ?
O2 C5 1.4508(15) . ?
O3 C8 1.3300(16) . ?
O3 C4 1.4493(16) . ?
O1 C2 1.4431(17) . ?
O1 C1 1.4420(19) . ?
O5 N1 1.3981(17) . ?
O5 N2 1.3851(19) . ?
O4 N6 1.4002(17) . ?
O4 N7 1.3884(18) . ?
N9 N8 1.2485(18) . ?
N9 N10 1.1125(19) . ?
N1 C6 1.2885(17) . ?
N2 C7 1.2912(18) . ?
N6 C8 1.2889(18) . ?
N8 C9 1.3892(19) . ?
N7 C9 1.2893(17) . ?
C6 C7 1.4246(19) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C5 C3 1.5059(18) . ?
C3 C4 1.5100(17) . ?
C3 C2 1.5343(18) . ?
C3 C1 1.5359(18) . ?
C8 C9 1.417(2) . ?
C7 N3 1.3807(19) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
N4 N3 1.2473(19) . ?
N4 N5 1.1094(19) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 O2 C5 115.33(10) . . ?
C8 O3 C4 116.27(10) . . ?
C1 O1 C2 90.79(9) . . ?
N2 O5 N1 111.02(10) . . ?
N7 O4 N6 111.01(10) . . ?
N10 N9 N8 171.15(17) . . ?
C6 N1 O5 104.44(12) . . ?
C7 N2 O5 105.14(11) . . ?
C8 N6 O4 104.33(12) . . ?
N9 N8 C9 115.43(13) . . ?
C9 N7 O4 104.69(12) . . ?
O2 C6 C7 123.95(12) . . ?
N1 C6 O2 125.98(12) . . ?
N1 C6 C7 110.07(12) . . ?
O2 C5 H5A 110.4 . . ?
O2 C5 H5B 110.4 . . ?
O2 C5 C3 106.64(10) . . ?
H5A C5 H5B 108.6 . . ?
C3 C5 H5A 110.4 . . ?
C3 C5 H5B 110.4 . . ?
C5 C3 C4 113.34(11) . . ?
C5 C3 C2 116.79(11) . . ?
C5 C3 C1 115.89(11) . . ?
C4 C3 C2 111.22(10) . . ?
C4 C3 C1 112.42(11) . . ?
C2 C3 C1 83.99(10) . . ?
O3 C8 C9 123.29(12) . . ?
N6 C8 O3 126.69(13) . . ?
N6 C8 C9 110.01(12) . . ?
N2 C7 C6 109.33(13) . . ?
N2 C7 N3 118.84(13) . . ?
N3 C7 C6 131.83(12) . . ?
N8 C9 C8 122.73(12) . . ?
N7 C9 N8 127.31(14) . . ?
N7 C9 C8 109.95(13) . . ?
O3 C4 C3 107.01(10) . . ?
O3 C4 H4A 110.3 . . ?
O3 C4 H4B 110.3 . . ?
C3 C4 H4A 110.3 . . ?
C3 C4 H4B 110.3 . . ?
H4A C4 H4B 108.6 . . ?
O1 C2 C3 91.59(10) . . ?
O1 C2 H2A 113.4 . . ?
O1 C2 H2B 113.4 . . ?
C3 C2 H2A 113.4 . . ?
C3 C2 H2B 113.4 . . ?
H2A C2 H2B 110.7 . . ?
O1 C1 C3 91.56(10) . . ?
O1 C1 H1A 113.4 . . ?
O1 C1 H1B 113.4 . . ?
C3 C1 H1A 113.4 . . ?
C3 C1 H1B 113.4 . . ?
H1A C1 H1B 110.7 . . ?
N5 N4 N3 169.83(17) . . ?
N4 N3 C7 116.47(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
O2 C6 C7 N2 -178.72(12) . . . . ?
O2 C6 C7 N3 1.0(2) . . . . ?
O2 C5 C3 C4 64.94(13) . . . . ?
O2 C5 C3 C2 -66.32(14) . . . . ?
O2 C5 C3 C1 -162.90(11) . . . . ?
O3 C8 C9 N8 0.1(2) . . . . ?
O3 C8 C9 N7 179.22(13) . . . . ?
O5 N1 C6 O2 178.64(12) . . . . ?
O5 N1 C6 C7 -0.64(16) . . . . ?
O5 N2 C7 C6 -0.21(15) . . . . ?
O5 N2 C7 N3 -179.93(12) . . . . ?
O4 N6 C8 O3 -179.39(13) . . . . ?
O4 N6 C8 C9 -0.34(16) . . . . ?
O4 N7 C9 N8 179.19(14) . . . . ?
O4 N7 C9 C8 0.14(16) . . . . ?
N9 N8 C9 N7 0.4(2) . . . . ?
N9 N8 C9 C8 179.32(14) . . . . ?
N1 O5 N2 C7 -0.18(16) . . . . ?
N1 C6 C7 N2 0.57(17) . . . . ?
N1 C6 C7 N3 -179.75(15) . . . . ?
N2 O5 N1 C6 0.53(16) . . . . ?
N2 C7 N3 N4 -172.57(14) . . . . ?
N6 O4 N7 C9 -0.36(17) . . . . ?
N6 C8 C9 N8 -178.97(14) . . . . ?
N6 C8 C9 N7 0.14(18) . . . . ?
N7 O4 N6 C8 0.44(17) . . . . ?
C6 O2 C5 C3 178.67(10) . . . . ?
C6 C7 N3 N4 7.8(2) . . . . ?
C5 O2 C6 N1 16.42(19) . . . . ?
C5 O2 C6 C7 -164.41(12) . . . . ?
C5 C3 C4 O3 59.79(14) . . . . ?
C5 C3 C2 O1 -126.58(11) . . . . ?
C5 C3 C1 O1 127.48(11) . . . . ?
C8 O3 C4 C3 169.17(11) . . . . ?
C4 O3 C8 N6 2.5(2) . . . . ?
C4 O3 C8 C9 -176.45(13) . . . . ?
C4 C3 C2 O1 101.19(11) . . . . ?
C4 C3 C1 O1 -99.94(11) . . . . ?
C2 O1 C1 C3 -11.18(10) . . . . ?
C2 C3 C4 O3 -166.25(11) . . . . ?
C2 C3 C1 O1 10.56(9) . . . . ?
C1 O1 C2 C3 11.19(10) . . . . ?
C1 C3 C4 O3 -74.04(14) . . . . ?
C1 C3 C2 O1 -10.56(9) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
