# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry A.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_220191295yto_0m
_database_code_depnum_ccdc_archive 'CCDC 2017267'
loop_
_audit_author_name
_audit_author_address
'Tingou Yan'
;nanjing university of science and technology
China
;
_audit_update_record             
;
2020-07-18 deposited with the CCDC.	2020-10-26 downloaded from the CCDC.
;
_audit_creation_date             2019-12-27
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C8 H3 N11 O8, H2 O, C3 H6 O'
_chemical_formula_sum            'C11 H11 N11 O10'
_chemical_formula_weight         457.31
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      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                   17.0881(10)
_cell_length_b                   6.1522(3)
_cell_length_c                   17.7676(11)
_cell_angle_alpha                90
_cell_angle_beta                 104.741(2)
_cell_angle_gamma                90
_cell_volume                     1806.42(18)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2045
_cell_measurement_temperature    170
_cell_measurement_theta_max      24.512
_cell_measurement_theta_min      2.370
_shelx_estimated_absorpt_T_max   0.994
_shelx_estimated_absorpt_T_min   0.974
_exptl_absorpt_coefficient_mu    0.149
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.4853
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1429 before and 0.0772 after correction. The Ratio of minimum to maximum transmission is 0.6511. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.682
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             936
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.04
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0989
_diffrn_reflns_av_unetI/netI     0.0938
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            11919
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.027
_diffrn_reflns_theta_max         25.027
_diffrn_reflns_theta_min         2.371
_diffrn_ambient_temperature      170.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1915
_reflns_number_total             3179
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.255
_refine_diff_density_min         -0.311
_refine_diff_density_rms         0.070
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     307
_refine_ls_number_reflns         3179
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.1208
_refine_ls_R_factor_gt           0.0583
_refine_ls_restrained_S_all      1.022
_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)+(0.0603P)²+0.6129P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1196
_refine_ls_wR_factor_ref         0.1542
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 H9B-H9
 2.1 with sigma of 0.02
 O9-H9B \\sim O9-H9A
 with sigma of 0.02
3.a Aromatic/amide H refined with riding coordinates:
 N7(H7)
3.b Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C10(H10A,H10B,H10C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O4 O 0.43434(15) -0.0880(4) 0.52058(16) 0.0330(7) Uani 1 1 d . . . . .
O9 O 0.55217(16) 0.7095(5) 0.35066(18) 0.0343(7) Uani 1 1 d D . . . .
O3 O 0.40606(15) -0.2113(5) 0.62536(17) 0.0382(8) Uani 1 1 d . . . . .
O10 O 0.11250(16) 0.5477(5) 0.45226(16) 0.0385(8) Uani 1 1 d . . . . .
O1 O 0.26437(17) -0.4285(5) 0.59940(16) 0.0379(7) Uani 1 1 d . . . . .
O8 O 0.29302(17) 1.4037(5) 0.21060(16) 0.0394(8) Uani 1 1 d . . . . .
O5 O 0.16065(16) 0.6796(5) 0.28754(17) 0.0404(8) Uani 1 1 d . . . . .
O7 O 0.18040(16) 1.2393(5) 0.21184(17) 0.0427(8) Uani 1 1 d . . . . .
N4 N 0.21152(18) 0.2069(5) 0.49003(18) 0.0247(8) Uani 1 1 d . . . . .
N9 N 0.40101(19) 0.8781(5) 0.31750(19) 0.0278(8) Uani 1 1 d . . . . .
O2 O 0.16122(18) -0.2626(5) 0.62401(17) 0.0447(8) Uani 1 1 d . . . . .
N7 N 0.40798(17) 0.3133(5) 0.44810(18) 0.0276(8) Uani 1 1 d . . . . .
H7 H 0.443415 0.213331 0.469763 0.033 Uiso 1 1 calc R . . . .
N2 N 0.38762(18) -0.1141(5) 0.5633(2) 0.0282(8) Uani 1 1 d . . . . .
N5 N 0.29406(17) 0.4903(5) 0.41521(17) 0.0259(8) Uani 1 1 d . . . . .
O6 O 0.15634(17) 0.9924(5) 0.34217(18) 0.0498(9) Uani 1 1 d . . . . .
N3 N 0.17780(17) 0.0575(5) 0.52653(18) 0.0267(8) Uani 1 1 d . . . . .
N8 N 0.18958(18) 0.8519(6) 0.31298(19) 0.0293(8) Uani 1 1 d . . . . .
N10 N 0.37761(18) 1.0597(5) 0.27606(18) 0.0279(8) Uani 1 1 d . . . . .
N6 N 0.42327(17) 0.4791(5) 0.40443(18) 0.0278(8) Uani 1 1 d . . . . .
N1 N 0.2192(2) -0.2705(6) 0.59637(19) 0.0316(8) Uani 1 1 d . . . . .
N11 N 0.2539(2) 1.2521(6) 0.22770(18) 0.0294(8) Uani 1 1 d . . . . .
C5 C 0.3523(2) 0.5814(6) 0.3854(2) 0.0240(9) Uani 1 1 d . . . . .
C4 C 0.3314(2) 0.3214(6) 0.4540(2) 0.0225(9) Uani 1 1 d . . . . .
C8 C 0.2991(2) 1.0726(6) 0.2710(2) 0.0245(9) Uani 1 1 d . . . . .
C1 C 0.2374(2) -0.0796(6) 0.5557(2) 0.0232(9) Uani 1 1 d . . . . .
C3 C 0.2903(2) 0.1691(6) 0.4937(2) 0.0227(9) Uani 1 1 d . . . . .
C2 C 0.3089(2) -0.0208(6) 0.5372(2) 0.0216(9) Uani 1 1 d . . . . .
C6 C 0.3393(2) 0.7751(6) 0.3383(2) 0.0235(9) Uani 1 1 d . . . . .
C7 C 0.2717(2) 0.9002(6) 0.3077(2) 0.0236(9) Uani 1 1 d . . . . .
C9 C 0.0479(2) 0.5803(7) 0.4048(2) 0.0320(10) Uani 1 1 d . . . . .
C11 C 0.0159(2) 0.4285(8) 0.3398(3) 0.0461(12) Uani 1 1 d . . . . .
H11A H 0.057638 0.321438 0.337164 0.069 Uiso 1 1 calc GR . . . .
H11B H 0.000688 0.509808 0.290784 0.069 Uiso 1 1 calc GR . . . .
H11C H -0.031706 0.353448 0.348229 0.069 Uiso 1 1 calc GR . . . .
C10 C -0.0009(3) 0.7769(8) 0.4121(3) 0.0546(14) Uani 1 1 d . . . . .
H10A H -0.052202 0.731916 0.422448 0.082 Uiso 1 1 calc GR . . . .
H10B H -0.011900 0.860142 0.363490 0.082 Uiso 1 1 calc GR . . . .
H10C H 0.029296 0.867584 0.455045 0.082 Uiso 1 1 calc GR . . . .
H4 H 0.181(3) 0.333(8) 0.471(3) 0.070(16) Uiso 1 1 d . . . . .
H9 H 0.452(3) 0.828(7) 0.324(3) 0.067(16) Uiso 1 1 d D . . . .
H9A H 0.574(3) 0.680(8) 0.311(2) 0.074(18) Uiso 1 1 d D . . . .
H9B H 0.536(3) 0.576(6) 0.362(3) 0.11(2) Uiso 1 1 d 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
O4 N2 1.244(4) . ?
O3 N2 1.223(4) . ?
O10 C9 1.224(4) . ?
O1 N1 1.233(4) . ?
O8 N11 1.230(4) . ?
O5 N8 1.208(4) . ?
O7 N11 1.217(4) . ?
N4 N3 1.337(4) . ?
N4 C3 1.351(4) . ?
N9 N10 1.342(4) . ?
N9 C6 1.359(5) . ?
O2 N1 1.214(4) . ?
N7 N6 1.347(4) . ?
N7 C4 1.340(4) . ?
N2 C2 1.427(4) . ?
N5 C5 1.362(5) . ?
N5 C4 1.319(5) . ?
O6 N8 1.220(4) . ?
N3 C1 1.323(5) . ?
N8 C7 1.460(5) . ?
N10 C8 1.323(4) . ?
N6 C5 1.331(4) . ?
N1 C1 1.453(5) . ?
N11 C8 1.452(5) . ?
C5 C6 1.441(5) . ?
C4 C3 1.456(5) . ?
C8 C7 1.388(5) . ?
C1 C2 1.392(5) . ?
C3 C2 1.392(5) . ?
C6 C7 1.381(5) . ?
C9 C11 1.479(6) . ?
C9 C10 1.493(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
N3 N4 C3 113.9(3) . . ?
N10 N9 C6 113.2(3) . . ?
C4 N7 N6 110.7(3) . . ?
O4 N2 C2 116.6(3) . . ?
O3 N2 O4 123.7(3) . . ?
O3 N2 C2 119.6(3) . . ?
C4 N5 C5 102.9(3) . . ?
C1 N3 N4 104.2(3) . . ?
O5 N8 O6 126.2(3) . . ?
O5 N8 C7 117.6(3) . . ?
O6 N8 C7 116.2(3) . . ?
C8 N10 N9 104.0(3) . . ?
C5 N6 N7 101.9(3) . . ?
O1 N1 C1 116.7(3) . . ?
O2 N1 O1 125.4(4) . . ?
O2 N1 C1 117.9(3) . . ?
O8 N11 C8 117.2(3) . . ?
O7 N11 O8 125.8(3) . . ?
O7 N11 C8 116.9(3) . . ?
N5 C5 C6 123.1(3) . . ?
N6 C5 N5 114.5(3) . . ?
N6 C5 C6 122.3(3) . . ?
N7 C4 C3 128.0(3) . . ?
N5 C4 N7 109.9(3) . . ?
N5 C4 C3 122.1(3) . . ?
N10 C8 N11 118.4(3) . . ?
N10 C8 C7 112.4(3) . . ?
C7 C8 N11 129.2(3) . . ?
N3 C1 N1 118.0(3) . . ?
N3 C1 C2 112.1(3) . . ?
C2 C1 N1 129.7(3) . . ?
N4 C3 C4 117.6(3) . . ?
N4 C3 C2 104.8(3) . . ?
C2 C3 C4 137.6(3) . . ?
C1 C2 N2 129.1(3) . . ?
C1 C2 C3 105.0(3) . . ?
C3 C2 N2 125.5(3) . . ?
N9 C6 C5 121.9(3) . . ?
N9 C6 C7 105.3(3) . . ?
C7 C6 C5 132.8(4) . . ?
C8 C7 N8 129.2(3) . . ?
C6 C7 N8 125.7(3) . . ?
C6 C7 C8 105.1(3) . . ?
O10 C9 C11 121.6(4) . . ?
O10 C9 C10 120.0(4) . . ?
C11 C9 C10 118.4(4) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N7 H7 O4 0.88 2.08 2.768(4) 133.8 . yes

_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_220191207_0m
_database_code_depnum_ccdc_archive 'CCDC 2017270'
loop_
_audit_author_name
_audit_author_address
'Tingou Yan'
;nanjing university of science and technology
China
;
_audit_update_record             
;
2020-07-18 deposited with the CCDC.	2020-10-26 downloaded from the CCDC.
;
_audit_creation_date             2019-12-03
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C8 H N11 O8, C3 H7 N O, 2(C2 H8 N)'
_chemical_formula_sum            'C15 H24 N14 O9'
_chemical_formula_weight         544.48
_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                   8.4189(3)
_cell_length_b                   12.1698(5)
_cell_length_c                   12.2467(5)
_cell_angle_alpha                101.7810(10)
_cell_angle_beta                 100.7690(10)
_cell_angle_gamma                93.9020(10)
_cell_volume                     1199.31(8)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    6539
_cell_measurement_temperature    170
_cell_measurement_theta_max      26.378
_cell_measurement_theta_min      2.701
_shelx_estimated_absorpt_T_max   0.990
_shelx_estimated_absorpt_T_min   0.976
_exptl_absorpt_coefficient_mu    0.126
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6126
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1232 before and 0.0626 after correction. The Ratio of minimum to maximum transmission is 0.8218. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.508
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0496
_diffrn_reflns_av_unetI/netI     0.0545
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            14214
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.401
_diffrn_reflns_theta_min         1.736
_diffrn_ambient_temperature      170.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'D8 VENTURE '
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3900
_reflns_number_total             4881
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.262
_refine_diff_density_min         -0.212
_refine_diff_density_rms         0.046
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     353
_refine_ls_number_reflns         4881
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0562
_refine_ls_R_factor_gt           0.0406
_refine_ls_restrained_S_all      1.027
_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)+(0.0377P)²+0.4332P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0944
_refine_ls_wR_factor_ref         0.1057
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 N2(H2A,H2B), N3(H3D,H3E)
2.b Aromatic/amide H refined with riding coordinates:
 C6(H6)
2.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C4(H4A,H4B,H4C), C2(H2C,H2D,H2E), C3(H3A,H3B,H3C), C5(H5A,
 H5B,H5C), C7(H7A,H7B,H7C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.96634(14) 0.67152(10) 0.70258(10) 0.0319(3) Uani 1 1 d . . . . .
O3 O 0.73931(14) 0.20885(10) 0.56743(11) 0.0335(3) Uani 1 1 d . . . . .
O5 O 0.42858(15) 0.23982(11) 0.72680(11) 0.0379(3) Uani 1 1 d . . . . .
O8 O 0.58334(15) 0.70581(11) 0.87199(11) 0.0344(3) Uani 1 1 d . . . . .
N10 N 0.72384(15) 0.45333(11) 0.76640(11) 0.0205(3) Uani 1 1 d . . . . .
N8 N 0.63976(15) 0.46811(12) 0.58349(11) 0.0218(3) Uani 1 1 d . . . . .
O2 O 1.21799(15) 0.67179(11) 0.68520(12) 0.0394(3) Uani 1 1 d . . . . .
N5 N 1.17619(15) 0.44903(11) 0.59947(11) 0.0217(3) Uani 1 1 d . . . . .
O4 O 0.94734(17) 0.13797(11) 0.51141(12) 0.0429(3) Uani 1 1 d . . . . .
O6 O 0.20789(16) 0.21076(11) 0.78880(12) 0.0436(4) Uani 1 1 d . . . . .
O7 O 0.41842(18) 0.75249(11) 0.98502(12) 0.0446(4) Uani 1 1 d . . . . .
N9 N 0.51691(15) 0.47994(12) 0.64073(11) 0.0203(3) Uani 1 1 d . . . . .
N12 N 0.23441(16) 0.42756(12) 0.89955(11) 0.0240(3) Uani 1 1 d . . . . .
N13 N 0.27529(16) 0.53938(12) 0.93791(11) 0.0245(3) Uani 1 1 d . . . . .
N6 N 1.12098(16) 0.33908(12) 0.56511(11) 0.0234(3) Uani 1 1 d . . . . .
O9 O 1.04890(16) 0.05753(12) 0.20945(13) 0.0473(4) Uani 1 1 d . . . . .
N2 N 0.26117(16) 0.17490(12) 0.40839(12) 0.0278(3) Uani 1 1 d . . . . .
H2A H 0.184577 0.145182 0.344146 0.033 Uiso 1 1 calc R . . . .
H2B H 0.212113 0.219407 0.458360 0.033 Uiso 1 1 calc R . . . .
N3 N 0.92883(16) 0.31871(12) 0.93326(11) 0.0263(3) Uani 1 1 d . . . . .
H3D H 1.003973 0.353719 0.903453 0.032 Uiso 1 1 calc R . . . .
H3E H 0.856244 0.368394 0.950113 0.032 Uiso 1 1 calc R . . . .
N4 N 1.08275(16) 0.62303(12) 0.67880(11) 0.0239(3) Uani 1 1 d . . . . .
N14 N 0.47263(16) 0.68264(12) 0.91844(11) 0.0256(3) Uani 1 1 d . . . . .
N7 N 0.87958(17) 0.21811(12) 0.55292(11) 0.0258(3) Uani 1 1 d . . . . .
N11 N 0.32425(17) 0.27238(12) 0.77978(12) 0.0268(3) Uani 1 1 d . . . . .
N1 N 0.77202(19) 0.03064(13) 0.15829(14) 0.0368(4) Uani 1 1 d . . . . .
C12 C 0.56735(17) 0.47033(13) 0.74783(12) 0.0187(3) Uani 1 1 d . . . . .
C9 C 0.91943(17) 0.42991(13) 0.63403(12) 0.0186(3) Uani 1 1 d . . . . .
C11 C 0.76061(17) 0.45258(13) 0.66240(12) 0.0177(3) Uani 1 1 d . . . . .
C10 C 0.96932(18) 0.32816(13) 0.58560(13) 0.0206(3) Uani 1 1 d . . . . .
C8 C 1.05741(17) 0.50224(13) 0.64033(12) 0.0187(3) Uani 1 1 d . . . . .
C14 C 0.33935(18) 0.39000(13) 0.83377(13) 0.0204(3) Uani 1 1 d . . . . .
C15 C 0.40347(18) 0.56690(13) 0.89366(13) 0.0206(3) Uani 1 1 d . . . . .
C13 C 0.45229(17) 0.47504(13) 0.82504(12) 0.0192(3) Uani 1 1 d . . . . .
C1 C 0.8419(2) 0.21940(15) 0.84601(15) 0.0315(4) Uani 1 1 d . . . . .
H1A H 0.786396 0.244459 0.779143 0.047 Uiso 1 1 calc GR . . . .
H1B H 0.761683 0.180443 0.877649 0.047 Uiso 1 1 calc GR . . . .
H1C H 0.920217 0.167641 0.823556 0.047 Uiso 1 1 calc GR . . . .
C4 C 0.3894(2) 0.24533(17) 0.37926(18) 0.0397(5) Uani 1 1 d . . . . .
H4A H 0.440864 0.198464 0.323745 0.060 Uiso 1 1 calc GR . . . .
H4B H 0.471378 0.278966 0.448281 0.060 Uiso 1 1 calc GR . . . .
H4C H 0.341342 0.305422 0.346379 0.060 Uiso 1 1 calc GR . . . .
C6 C 0.9117(3) 0.05866(17) 0.23184(18) 0.0426(5) Uani 1 1 d . . . . .
H6 H 0.906478 0.082077 0.309874 0.051 Uiso 1 1 calc R . . . .
C2 C 1.0112(2) 0.29035(18) 1.03919(16) 0.0416(5) Uani 1 1 d . . . . .
H2C H 1.088471 0.235911 1.021792 0.062 Uiso 1 1 calc GR . . . .
H2D H 0.930305 0.257224 1.074702 0.062 Uiso 1 1 calc GR . . . .
H2E H 1.069703 0.359020 1.091666 0.062 Uiso 1 1 calc GR . . . .
C3 C 0.3225(3) 0.08199(17) 0.45912(19) 0.0446(5) Uani 1 1 d . . . . .
H3A H 0.368801 0.030621 0.403795 0.067 Uiso 1 1 calc GR . . . .
H3B H 0.232796 0.040530 0.479721 0.067 Uiso 1 1 calc GR . . . .
H3C H 0.406782 0.113124 0.527546 0.067 Uiso 1 1 calc GR . . . .
C5 C 0.7650(3) -0.00807(19) 0.03784(18) 0.0497(5) Uani 1 1 d . . . . .
H5A H 0.712981 -0.086031 0.012614 0.075 Uiso 1 1 calc GR . . . .
H5B H 0.875500 -0.004939 0.023128 0.075 Uiso 1 1 calc GR . . . .
H5C H 0.701656 0.040454 -0.004041 0.075 Uiso 1 1 calc GR . . . .
C7 C 0.6188(3) 0.0326(2) 0.1962(2) 0.0550(6) Uani 1 1 d . . . . .
H7A H 0.639891 0.057689 0.279389 0.082 Uiso 1 1 calc GR . . . .
H7B H 0.559787 -0.043427 0.173424 0.082 Uiso 1 1 calc GR . . . .
H7C H 0.553161 0.084775 0.161449 0.082 Uiso 1 1 calc GR . . . .
H9 H 0.418(3) 0.4867(17) 0.6063(17) 0.038(6) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 N4 1.2283(17) . ?
O3 N7 1.2278(17) . ?
O5 N11 1.2267(18) . ?
O8 N14 1.2247(17) . ?
N10 C12 1.3321(18) . ?
N10 C11 1.3643(19) . ?
N8 N9 1.3535(17) . ?
N8 C11 1.3183(19) . ?
O2 N4 1.2289(18) . ?
N5 N6 1.3401(19) . ?
N5 C8 1.3462(19) . ?
O4 N7 1.2315(18) . ?
O6 N11 1.2281(18) . ?
O7 N14 1.2266(18) . ?
N9 C12 1.333(2) . ?
N9 H9 0.88(2) . ?
N12 N13 1.3438(19) . ?
N12 C14 1.3450(19) . ?
N13 C15 1.3467(19) . ?
N6 C10 1.3495(19) . ?
O9 C6 1.237(2) . ?
N2 H2A 0.9100 . ?
N2 H2B 0.9100 . ?
N2 C4 1.473(2) . ?
N2 C3 1.476(2) . ?
N3 H3D 0.9100 . ?
N3 H3E 0.9100 . ?
N3 C1 1.483(2) . ?
N3 C2 1.470(2) . ?
N4 C8 1.437(2) . ?
N14 C15 1.436(2) . ?
N7 C10 1.434(2) . ?
N11 C14 1.435(2) . ?
N1 C6 1.317(3) . ?
N1 C5 1.443(3) . ?
N1 C7 1.451(3) . ?
C12 C13 1.471(2) . ?
C9 C11 1.4729(19) . ?
C9 C10 1.388(2) . ?
C9 C8 1.389(2) . ?
C14 C13 1.391(2) . ?
C15 C13 1.390(2) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C6 H6 0.9500 . ?
C2 H2C 0.9800 . ?
C2 H2D 0.9800 . ?
C2 H2E 0.9800 . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C12 N10 C11 101.82(12) . . ?
C11 N8 N9 102.07(12) . . ?
N6 N5 C8 106.94(12) . . ?
N8 N9 H9 121.6(13) . . ?
C12 N9 N8 110.35(12) . . ?
C12 N9 H9 127.9(13) . . ?
N13 N12 C14 106.90(12) . . ?
N12 N13 C15 106.81(12) . . ?
N5 N6 C10 106.84(12) . . ?
H2A N2 H2B 107.7 . . ?
C4 N2 H2A 108.9 . . ?
C4 N2 H2B 108.9 . . ?
C4 N2 C3 113.36(15) . . ?
C3 N2 H2A 108.9 . . ?
C3 N2 H2B 108.9 . . ?
H3D N3 H3E 107.7 . . ?
C1 N3 H3D 108.8 . . ?
C1 N3 H3E 108.8 . . ?
C2 N3 H3D 108.8 . . ?
C2 N3 H3E 108.8 . . ?
C2 N3 C1 113.69(14) . . ?
O1 N4 O2 123.87(15) . . ?
O1 N4 C8 117.52(13) . . ?
O2 N4 C8 118.61(13) . . ?
O8 N14 O7 123.70(14) . . ?
O8 N14 C15 117.86(13) . . ?
O7 N14 C15 118.45(13) . . ?
O3 N7 O4 123.55(14) . . ?
O3 N7 C10 118.31(13) . . ?
O4 N7 C10 118.14(13) . . ?
O5 N11 O6 124.07(15) . . ?
O5 N11 C14 117.63(13) . . ?
O6 N11 C14 118.30(14) . . ?
C6 N1 C5 121.64(18) . . ?
C6 N1 C7 121.01(18) . . ?
C5 N1 C7 117.29(17) . . ?
N10 C12 N9 110.38(13) . . ?
N10 C12 C13 129.50(14) . . ?
N9 C12 C13 120.08(13) . . ?
C10 C9 C11 128.93(14) . . ?
C10 C9 C8 99.75(13) . . ?
C8 C9 C11 131.22(15) . . ?
N10 C11 C9 124.27(13) . . ?
N8 C11 N10 115.37(13) . . ?
N8 C11 C9 120.27(13) . . ?
N6 C10 N7 118.29(13) . . ?
N6 C10 C9 113.21(14) . . ?
C9 C10 N7 128.47(14) . . ?
N5 C8 N4 118.41(13) . . ?
N5 C8 C9 113.27(14) . . ?
C9 C8 N4 128.25(14) . . ?
N12 C14 N11 119.46(14) . . ?
N12 C14 C13 113.35(14) . . ?
C13 C14 N11 127.18(13) . . ?
N13 C15 N14 119.48(13) . . ?
N13 C15 C13 113.35(14) . . ?
C13 C15 N14 127.17(13) . . ?
C14 C13 C12 128.87(14) . . ?
C15 C13 C12 130.62(14) . . ?
C15 C13 C14 99.59(13) . . ?
N3 C1 H1A 109.5 . . ?
N3 C1 H1B 109.5 . . ?
N3 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
N2 C4 H4A 109.5 . . ?
N2 C4 H4B 109.5 . . ?
N2 C4 H4C 109.5 . . ?
H4A C4 H4B 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
O9 C6 N1 126.5(2) . . ?
O9 C6 H6 116.8 . . ?
N1 C6 H6 116.8 . . ?
N3 C2 H2C 109.5 . . ?
N3 C2 H2D 109.5 . . ?
N3 C2 H2E 109.5 . . ?
H2C C2 H2D 109.5 . . ?
H2C C2 H2E 109.5 . . ?
H2D C2 H2E 109.5 . . ?
N2 C3 H3A 109.5 . . ?
N2 C3 H3B 109.5 . . ?
N2 C3 H3C 109.5 . . ?
H3A C3 H3B 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
N1 C5 H5A 109.5 . . ?
N1 C5 H5B 109.5 . . ?
N1 C5 H5C 109.5 . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
N1 C7 H7A 109.5 . . ?
N1 C7 H7B 109.5 . . ?
N1 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?

_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_zz
_database_code_depnum_ccdc_archive 'CCDC 2017271'
loop_
_audit_author_name
_audit_author_address
'Tingou Yan'
;nanjing university of science and technology
China
;
_audit_update_record             
;
2020-07-18 deposited with the CCDC.	2020-10-26 downloaded from the CCDC.
;
_audit_creation_date             2019-12-16
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C10 H4 N14 O8, 4(C3 H7 N O), 4(H2 O)'
_chemical_formula_sum            'C22 H40 N18 O16'
_chemical_formula_weight         812.72
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   7.1057(4)
_cell_length_b                   10.8374(8)
_cell_length_c                   13.6606(8)
_cell_angle_alpha                67.0870(10)
_cell_angle_beta                 87.001(2)
_cell_angle_gamma                85.154(2)
_cell_volume                     965.28(11)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    4242
_cell_measurement_temperature    170
_cell_measurement_theta_max      25.64
_cell_measurement_theta_min      2.877
_shelx_estimated_absorpt_T_max   0.991
_shelx_estimated_absorpt_T_min   0.978
_exptl_absorpt_coefficient_mu    0.119
_exptl_absorpt_correction_T_max  0.7453
_exptl_absorpt_correction_T_min  0.6748
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1129 before and 0.0538 after correction. The Ratio of minimum to maximum transmission is 0.9054. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.398
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             426
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0415
_diffrn_reflns_av_unetI/netI     0.0478
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            10619
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.682
_diffrn_reflns_theta_min         2.878
_diffrn_ambient_temperature      170.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2828
_reflns_number_total             3646
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.520
_refine_diff_density_min         -0.465
_refine_diff_density_rms         0.046
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     281
_refine_ls_number_reflns         3646
_refine_ls_number_restraints     7
_refine_ls_R_factor_all          0.0694
_refine_ls_R_factor_gt           0.0494
_refine_ls_restrained_S_all      1.043
_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)+(0.0513P)²+0.4918P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1141
_refine_ls_wR_factor_ref         0.1275
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 O5-H5A \\sim O5-H5B \\sim O6-H6B \\sim O6-H6A
 with sigma of 0.02
 N2-H2 \\sim N7-H7
 with sigma of 0.02
3.a Aromatic/amide H refined with riding coordinates:
 C9(H9), C6(H6)
3.b Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C11(H11A,H11B,H11C), C7(H7A,H7B,H7C), C8(H8A,H8B,H8C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O4 O 0.6605(2) 0.89533(14) 0.32647(12) 0.0419(4) Uani 1 1 d . . . . .
O2 O 1.0324(2) 0.36112(15) 0.27731(13) 0.0423(4) Uani 1 1 d . . . . .
N5 N 0.9988(2) 0.84795(15) 0.12491(13) 0.0255(4) Uani 1 1 d . . . . .
O1 O 1.0068(3) 0.54818(16) 0.13903(12) 0.0485(5) Uani 1 1 d . . . . .
O3 O 0.5564(2) 0.75104(16) 0.47575(13) 0.0456(4) Uani 1 1 d . . . . .
O8 O 0.9316(2) 0.23163(15) 0.53589(13) 0.0442(4) Uani 1 1 d . . . . .
O6 O 0.3540(3) 0.51888(18) 0.32901(13) 0.0462(4) Uani 1 1 d D . . . .
N3 N 0.7597(2) 0.55190(16) 0.44560(13) 0.0291(4) Uani 1 1 d . . . . .
N7 N 0.6920(2) 0.86364(16) 0.11311(13) 0.0279(4) Uani 1 1 d D . . . .
N6 N 0.7504(2) 0.96800(16) 0.02631(13) 0.0300(4) Uani 1 1 d . . . . .
N2 N 0.8546(2) 0.47485(17) 0.40111(13) 0.0286(4) Uani 1 1 d D . . . .
N1 N 0.9846(2) 0.48082(17) 0.23336(14) 0.0328(4) Uani 1 1 d . . . . .
N4 N 0.6459(2) 0.78059(17) 0.39170(14) 0.0324(4) Uani 1 1 d . . . . .
N9 N 0.8213(3) 0.02427(18) 0.59952(15) 0.0398(5) Uani 1 1 d . . . . .
O5 O 0.3663(2) 0.7794(2) 0.20323(18) 0.0750(8) Uani 1 1 d D . . . .
O7 O 0.6011(3) 0.3737(2) 0.24465(18) 0.0701(6) Uani 1 1 d . . . . .
C4 C 0.8397(3) 0.79436(18) 0.17004(15) 0.0238(4) Uani 1 1 d . . . . .
C1 C 0.7427(3) 0.67254(19) 0.36778(15) 0.0253(4) Uani 1 1 d . . . . .
C5 C 0.9364(3) 0.95378(18) 0.03765(15) 0.0245(4) Uani 1 1 d . . . . .
C2 C 0.8250(3) 0.67822(19) 0.27119(15) 0.0239(4) Uani 1 1 d . . . . .
C3 C 0.8930(3) 0.54679(19) 0.29818(15) 0.0261(4) Uani 1 1 d . . . . .
N8 N 0.5463(4) 0.3106(3) 0.1100(2) 0.0680(7) Uani 1 1 d . . . . .
C9 C 0.8450(3) 0.1438(2) 0.52533(18) 0.0389(5) Uani 1 1 d . . . . .
H9 H 0.790971 0.164082 0.458177 0.047 Uiso 1 1 calc R . . . .
C10 C 0.7116(4) -0.0705(2) 0.5805(2) 0.0515(7) Uani 1 1 d . . . . .
H10A H 0.595142 -0.082889 0.623961 0.077 Uiso 1 1 calc GR . . . .
H10B H 0.785562 -0.156859 0.599629 0.077 Uiso 1 1 calc GR . . . .
H10C H 0.679944 -0.036086 0.505197 0.077 Uiso 1 1 calc GR . . . .
C6 C 0.4973(4) 0.3640(3) 0.1799(3) 0.0608(8) Uani 1 1 d . . . . .
H6 H 0.369662 0.398158 0.180040 0.073 Uiso 1 1 calc R . . . .
C11 C 0.8860(5) -0.0118(3) 0.7058(2) 0.0683(9) Uani 1 1 d . . . . .
H11A H 0.965805 0.056889 0.707290 0.102 Uiso 1 1 calc GR . . . .
H11B H 0.959270 -0.098695 0.728447 0.102 Uiso 1 1 calc GR . . . .
H11C H 0.777022 -0.018235 0.754171 0.102 Uiso 1 1 calc GR . . . .
C7 C 0.7416(7) 0.2585(5) 0.1038(4) 0.1153(16) Uani 1 1 d . . . . .
H7A H 0.823135 0.291559 0.142570 0.173 Uiso 1 1 calc GR . . . .
H7B H 0.783734 0.288876 0.029164 0.173 Uiso 1 1 calc GR . . . .
H7C H 0.748552 0.160102 0.135436 0.173 Uiso 1 1 calc GR . . . .
C8 C 0.4075(8) 0.2976(5) 0.0404(3) 0.1293(19) Uani 1 1 d . . . . .
H8A H 0.387851 0.202441 0.060099 0.194 Uiso 1 1 calc GR . . . .
H8B H 0.453564 0.336167 -0.033441 0.194 Uiso 1 1 calc GR . . . .
H8C H 0.287831 0.345495 0.047862 0.194 Uiso 1 1 calc GR . . . .
H7 H 0.564(3) 0.847(2) 0.132(2) 0.051(7) Uiso 1 1 d D . . . .
H5A H 0.360(5) 0.693(2) 0.249(2) 0.085(11) Uiso 1 1 d D . . . .
H6A H 0.336(4) 0.489(3) 0.3987(16) 0.076(10) Uiso 1 1 d D . . . .
H6B H 0.445(4) 0.466(3) 0.314(3) 0.086(11) Uiso 1 1 d D . . . .
H5B H 0.258(4) 0.800(4) 0.167(3) 0.120(15) Uiso 1 1 d D . . . .
H2 H 0.889(4) 0.383(2) 0.443(2) 0.058(8) Uiso 1 1 d 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
O4 N4 1.225(2) . ?
O2 N1 1.224(2) . ?
N5 C4 1.325(2) . ?
N5 C5 1.356(2) . ?
O1 N1 1.218(2) . ?
O3 N4 1.224(2) . ?
O8 C9 1.233(3) . ?
O6 H6A 0.88(2) . ?
O6 H6B 0.90(2) . ?
N3 N2 1.334(2) . ?
N3 C1 1.326(2) . ?
N7 N6 1.357(2) . ?
N7 C4 1.329(2) . ?
N7 H7 0.94(2) . ?
N6 C5 1.328(2) . ?
N2 C3 1.342(2) . ?
N2 H2 0.95(2) . ?
N1 C3 1.440(3) . ?
N4 C1 1.445(3) . ?
N9 C9 1.315(3) . ?
N9 C10 1.447(3) . ?
N9 C11 1.439(3) . ?
O5 H5A 0.91(2) . ?
O5 H5B 0.90(2) . ?
O7 C6 1.221(3) . ?
C4 C2 1.469(3) . ?
C1 C2 1.396(3) . ?
C5 C5 1.460(4) 2_775 ?
C2 C3 1.375(3) . ?
N8 C6 1.315(4) . ?
N8 C7 1.465(5) . ?
N8 C8 1.456(5) . ?
C9 H9 0.9500 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C6 H6 0.9500 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C4 N5 C5 102.42(15) . . ?
H6A O6 H6B 109(3) . . ?
C1 N3 N2 104.45(16) . . ?
N6 N7 H7 124.0(15) . . ?
C4 N7 N6 110.14(16) . . ?
C4 N7 H7 125.8(15) . . ?
C5 N6 N7 101.92(15) . . ?
N3 N2 C3 110.51(16) . . ?
N3 N2 H2 120.0(17) . . ?
C3 N2 H2 129.4(17) . . ?
O2 N1 C3 117.35(17) . . ?
O1 N1 O2 125.20(18) . . ?
O1 N1 C3 117.45(17) . . ?
O4 N4 C1 117.48(17) . . ?
O3 N4 O4 124.75(18) . . ?
O3 N4 C1 117.77(17) . . ?
C9 N9 C10 121.2(2) . . ?
C9 N9 C11 121.2(2) . . ?
C11 N9 C10 117.3(2) . . ?
H5A O5 H5B 105(3) . . ?
N5 C4 N7 110.58(16) . . ?
N5 C4 C2 125.40(17) . . ?
N7 C4 C2 123.97(17) . . ?
N3 C1 N4 117.89(17) . . ?
N3 C1 C2 114.07(17) . . ?
C2 C1 N4 128.03(17) . . ?
N5 C5 C5 122.6(2) . 2_775 ?
N6 C5 N5 114.95(16) . . ?
N6 C5 C5 122.4(2) . 2_775 ?
C1 C2 C4 129.18(18) . . ?
C3 C2 C4 130.01(18) . . ?
C3 C2 C1 100.78(16) . . ?
N2 C3 N1 119.57(17) . . ?
N2 C3 C2 110.18(18) . . ?
C2 C3 N1 130.18(18) . . ?
C6 N8 C7 120.1(3) . . ?
C6 N8 C8 121.1(3) . . ?
C8 N8 C7 118.8(3) . . ?
O8 C9 N9 125.3(2) . . ?
O8 C9 H9 117.4 . . ?
N9 C9 H9 117.4 . . ?
N9 C10 H10A 109.5 . . ?
N9 C10 H10B 109.5 . . ?
N9 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
O7 C6 N8 125.8(3) . . ?
O7 C6 H6 117.1 . . ?
N8 C6 H6 117.1 . . ?
N9 C11 H11A 109.5 . . ?
N9 C11 H11B 109.5 . . ?
N9 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N8 C7 H7A 109.5 . . ?
N8 C7 H7B 109.5 . . ?
N8 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N8 C8 H8A 109.5 . . ?
N8 C8 H8B 109.5 . . ?
N8 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N7 H7 O5 0.94(2) 1.72(2) 2.625(2) 161(2) . yes
O5 H5A O6 0.91(2) 1.77(2) 2.679(3) 174(3) . yes
O6 H6B O7 0.90(2) 1.89(2) 2.760(3) 164(3) . yes
O5 H5B N5 0.90(2) 1.92(2) 2.804(2) 164(4) 1_455 yes
N2 H2 O8 0.95(2) 1.65(2) 2.592(2) 168(3) . yes

_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_zz_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2017268'
loop_
_audit_author_name
_audit_author_address
'Tingou Yan'
;nanjing university of science and technology
China
;
_audit_update_record             
;
2020-07-18 deposited with the CCDC.	2020-10-26 downloaded from the CCDC.
;
_audit_creation_date             2019-12-25
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C H4 O), C5 H2 N7 O4'
_chemical_formula_sum            'C7 H10 N7 O6'
_chemical_formula_weight         288.22
_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                   9.3737(4)
_cell_length_b                   8.4417(3)
_cell_length_c                   15.5365(7)
_cell_angle_alpha                90
_cell_angle_beta                 90.12(5)
_cell_angle_gamma                90
_cell_volume                     1229.40(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3702
_cell_measurement_temperature    170
_cell_measurement_theta_max      26.302
_cell_measurement_theta_min      2.622
_shelx_estimated_absorpt_T_max   0.989
_shelx_estimated_absorpt_T_min   0.980
_exptl_absorpt_coefficient_mu    0.136
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.6976
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0982 before and 0.0520 after correction. The Ratio of minimum to maximum transmission is 0.9357. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.557
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             596
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0543
_diffrn_reflns_av_unetI/netI     0.0414
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            14430
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.238
_diffrn_reflns_theta_min         2.622
_diffrn_ambient_temperature      170.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2000
_reflns_number_total             2740
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.293
_refine_diff_density_min         -0.270
_refine_diff_density_rms         0.053
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     195
_refine_ls_number_reflns         2740
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0723
_refine_ls_R_factor_gt           0.0454
_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)+(0.0530P)²+0.8086P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1053
_refine_ls_wR_factor_ref         0.1232
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N3(H3)
2.b Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C), C7(H7A,H7B,H7C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O6 O 0.70634(15) 1.04781(17) 0.51208(10) 0.0304(4) Uani 1 1 d . . . . .
O5 O 0.1087(2) 0.8265(2) 0.36444(11) 0.0504(5) Uani 1 1 d . . . . .
O1 O 0.14076(16) 0.2620(2) 0.36705(12) 0.0448(4) Uani 1 1 d . . . . .
N2 N 0.40837(17) 0.24748(19) 0.42589(10) 0.0246(4) Uani 1 1 d . . . . .
O4 O 0.47088(19) 0.74652(18) 0.35356(11) 0.0451(4) Uani 1 1 d . . . . .
O2 O 0.19133(18) 0.4741(2) 0.29410(12) 0.0484(5) Uani 1 1 d . . . . .
N5 N 0.91795(17) 0.6140(2) 0.41213(11) 0.0253(4) Uani 1 1 d . . . . .
N3 N 0.54329(16) 0.28481(19) 0.44559(10) 0.0232(4) Uani 1 1 d . . . . .
H3 H 0.597923 0.225744 0.478698 0.028 Uiso 1 1 calc R . . . .
N6 N 0.81816(16) 0.41976(19) 0.48477(10) 0.0245(4) Uani 1 1 d . . . . .
N7 N 0.46911(18) 0.6233(2) 0.31342(11) 0.0283(4) Uani 1 1 d . . . . .
N4 N 0.78548(17) 0.60053(19) 0.37811(11) 0.0258(4) Uani 1 1 d . . . . .
N1 N 0.22248(18) 0.3656(2) 0.34266(11) 0.0303(4) Uani 1 1 d . . . . .
O3 O 0.4644(2) 0.6134(2) 0.23573(10) 0.0550(5) Uani 1 1 d . . . . .
C2 C 0.4731(2) 0.4765(2) 0.36254(12) 0.0221(4) Uani 1 1 d . . . . .
C5 C 0.9351(2) 0.5069(2) 0.47472(13) 0.0241(4) Uani 1 1 d . . . . .
C3 C 0.5874(2) 0.4219(2) 0.40972(12) 0.0219(4) Uani 1 1 d . . . . .
C4 C 0.7310(2) 0.4823(2) 0.42374(12) 0.0225(4) Uani 1 1 d . . . . .
C1 C 0.36650(19) 0.3644(2) 0.37515(12) 0.0233(4) Uani 1 1 d . . . . .
C6 C 0.1486(3) 0.8860(3) 0.28322(15) 0.0419(6) Uani 1 1 d . . . . .
H6A H 0.111802 0.816027 0.238001 0.063 Uiso 1 1 calc GR . . . .
H6B H 0.252870 0.890855 0.279568 0.063 Uiso 1 1 calc GR . . . .
H6C H 0.108880 0.992476 0.275617 0.063 Uiso 1 1 calc GR . . . .
C7 C 0.7951(3) 1.0038(3) 0.44032(19) 0.0526(7) Uani 1 1 d . . . . .
H7A H 0.738550 0.943030 0.398701 0.079 Uiso 1 1 calc GR . . . .
H7B H 0.874840 0.938868 0.460868 0.079 Uiso 1 1 calc GR . . . .
H7C H 0.832155 1.099533 0.412585 0.079 Uiso 1 1 calc GR . . . .
H5 H 0.982(3) 0.689(3) 0.3913(16) 0.048(7) Uiso 1 1 d . . . . .
H6 H 0.676(3) 0.961(3) 0.5343(18) 0.055(8) Uiso 1 1 d . . . . .
H5A H 0.169(3) 0.854(4) 0.402(2) 0.070(10) 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
O6 C7 1.441(3) . ?
O6 H6 0.86(3) . ?
O5 C6 1.409(3) . ?
O5 H5A 0.84(3) . ?
O1 N1 1.223(2) . ?
N2 N3 1.338(2) . ?
N2 C1 1.322(2) . ?
O4 N7 1.213(2) . ?
O2 N1 1.222(2) . ?
N5 N4 1.353(2) . ?
N5 C5 1.337(3) . ?
N5 H5 0.93(3) . ?
N3 H3 0.8800 . ?
N3 C3 1.350(2) . ?
N6 C5 1.330(2) . ?
N6 C4 1.358(3) . ?
N7 O3 1.211(2) . ?
N7 C2 1.456(2) . ?
N4 C4 1.327(2) . ?
N1 C1 1.440(2) . ?
C2 C3 1.376(3) . ?
C2 C1 1.390(3) . ?
C5 C5 1.451(4) 3_766 ?
C3 C4 1.455(3) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7 O6 H6 106.4(19) . . ?
C6 O5 H5A 110(2) . . ?
C1 N2 N3 103.88(15) . . ?
N4 N5 H5 120.9(16) . . ?
C5 N5 N4 109.63(16) . . ?
C5 N5 H5 129.4(16) . . ?
N2 N3 H3 123.3 . . ?
N2 N3 C3 113.43(16) . . ?
C3 N3 H3 123.3 . . ?
C5 N6 C4 101.44(16) . . ?
O4 N7 C2 117.39(17) . . ?
O3 N7 O4 124.91(18) . . ?
O3 N7 C2 117.70(17) . . ?
C4 N4 N5 102.05(15) . . ?
O1 N1 C1 118.28(17) . . ?
O2 N1 O1 125.34(18) . . ?
O2 N1 C1 116.36(17) . . ?
C3 C2 N7 125.69(17) . . ?
C3 C2 C1 104.82(16) . . ?
C1 C2 N7 129.46(17) . . ?
N5 C5 C5 123.2(2) . 3_766 ?
N6 C5 N5 111.19(17) . . ?
N6 C5 C5 125.6(2) . 3_766 ?
N3 C3 C2 105.56(16) . . ?
N3 C3 C4 121.50(17) . . ?
C2 C3 C4 132.93(18) . . ?
N6 C4 C3 121.58(17) . . ?
N4 C4 N6 115.69(17) . . ?
N4 C4 C3 122.72(17) . . ?
N2 C1 N1 119.39(17) . . ?
N2 C1 C2 112.31(17) . . ?
C2 C1 N1 128.27(17) . . ?
O5 C6 H6A 109.5 . . ?
O5 C6 H6B 109.5 . . ?
O5 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
O6 C7 H7A 109.5 . . ?
O6 C7 H7B 109.5 . . ?
O6 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N3 H3 O6 0.88 1.89 2.720(2) 157.6 1_545 yes
N5 H5 O5 0.93(3) 1.71(3) 2.640(2) 174(2) 1_655 yes
O6 H6 N2 0.86(3) 2.03(3) 2.882(2) 173(3) 3_666 yes
O5 H5A O6 0.84(3) 1.96(3) 2.793(3) 170(3) 3_676 yes

_olex2_submission_special_instructions 'No special instructions were received'
