# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2019

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

data_mo_2017276-nlg-x-98_0m
_audit_block_doi                 10.5517/ccdc.csd.cc1ps69z
_database_code_depnum_ccdc_archive 'CCDC 1572391'
_audit_update_record             
;
2017-09-04 deposited with the CCDC.	2019-04-26 downloaded from the CCDC.
;
_audit_creation_date             2017-04-21
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5335)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C4 H2 N8'
_chemical_formula_sum            'C4 H2 N8'
_chemical_formula_weight         162.14
_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'

_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                   7.814(2)
_cell_length_b                   11.758(3)
_cell_length_c                   15.119(4)
_cell_angle_alpha                90
_cell_angle_beta                 102.668(6)
_cell_angle_gamma                90
_cell_volume                     1355.4(7)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    2265
_cell_measurement_temperature    173
_cell_measurement_theta_max      27.49
_cell_measurement_theta_min      2.67
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.120
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6600
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.0721 before and 0.0498 after correction. The Ratio of minimum to maximum transmission is 0.8852. The λ/2 correction factor is 0.00150.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.589
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?

_exptl_crystal_description       needle
_exptl_crystal_F_000             656
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.04
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0319
_diffrn_reflns_av_unetI/netI     0.0381
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            8736
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.598
_diffrn_reflns_theta_min         2.215
_diffrn_ambient_temperature      173
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2229
_reflns_number_total             3071
_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 v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_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         0.220
_refine_diff_density_min         -0.267
_refine_diff_density_rms         0.065
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         3071
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0634
_refine_ls_R_factor_gt           0.0440
_refine_ls_restrained_S_all      1.024
_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)+(0.0880P)²+0.0300P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1263
_refine_ls_wR_factor_ref         0.1432
_refine_special_details          ?
_olex2_refinement_description    
;
1. Others
 Fixed Uiso: H10A(0.035) H10B(0.035) H5A(0.036) H5B(0.036)
 Fixed X: H10A(0.6027) H10B(0.673) H5A(-0.036) H5B(-0.1105)
 Fixed Y: H10A(0.4779) H10B(0.5428) H5A(0.7692) H5B(0.7031)
 Fixed Z: H10A(0.1804) H10B(0.1086) H5A(0.839) H5B(0.9087)
;
_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
N4 N 0.00949(16) 0.61343(9) 0.74059(9) 0.0261(3) Uani 1 1 d . . . . .
N13 N 0.51284(16) 0.63735(9) 0.26259(9) 0.0272(3) Uani 1 1 d . . . . .
N10 N 0.62481(16) 0.54270(10) 0.15606(9) 0.0290(3) Uani 1 1 d . . . . .
H10A H 0.6027 0.4779 0.1804 0.035 Uiso 1 1 calc R . . . .
H10B H 0.6730 0.5428 0.1086 0.035 Uiso 1 1 calc R . . . .
N2 N -0.09254(17) 0.40625(10) 0.79869(9) 0.0302(3) Uani 1 1 d . . . . .
N5 N -0.06855(17) 0.70436(10) 0.85927(9) 0.0303(3) Uani 1 1 d . . . . .
H5A H -0.0360 0.7692 0.8390 0.036 Uiso 1 1 calc R . . . .
H5B H -0.1105 0.7031 0.9087 0.036 Uiso 1 1 calc R . . . .
N3 N -0.02684(18) 0.41155(10) 0.72431(9) 0.0326(3) Uani 1 1 d . . . . .
N11 N 0.57246(17) 0.84461(10) 0.18891(10) 0.0322(3) Uani 1 1 d . . . . .
N12 N 0.49609(18) 0.84099(10) 0.25924(10) 0.0339(3) Uani 1 1 d . . . . .
N7 N 0.13085(18) 0.60586(12) 0.59703(10) 0.0367(3) Uani 1 1 d . . . . .
N14 N 0.39454(19) 0.74396(11) 0.36629(10) 0.0359(3) Uani 1 1 d . . . . .
N15 N 0.37786(18) 0.64806(12) 0.40102(9) 0.0351(3) Uani 1 1 d . . . . .
N1 N -0.23664(18) 0.48675(11) 0.98559(10) 0.0393(4) Uani 1 1 d . . . . .
N6 N 0.0831(2) 0.51030(11) 0.62083(10) 0.0383(4) Uani 1 1 d . . . . .
N9 N 0.7668(2) 0.76054(12) 0.01958(11) 0.0432(4) Uani 1 1 d . . . . .
C3 C -0.05461(18) 0.60924(11) 0.81560(10) 0.0242(3) Uani 1 1 d . . . . .
C5 C 0.58581(17) 0.63965(11) 0.19060(10) 0.0237(3) Uani 1 1 d . . . . .
N16 N 0.3548(2) 0.56992(14) 0.43836(11) 0.0486(4) Uani 1 1 d . . . . .
C2 C -0.10762(19) 0.50050(11) 0.84365(10) 0.0251(3) Uani 1 1 d . . . . .
C6 C 0.61733(19) 0.74856(12) 0.15476(10) 0.0262(3) Uani 1 1 d . . . . .
N8 N 0.1774(2) 0.68413(14) 0.56865(11) 0.0487(4) Uani 1 1 d . . . . .
C4 C 0.01921(19) 0.51496(12) 0.69973(10) 0.0275(3) Uani 1 1 d . . . . .
C1 C -0.1802(2) 0.49008(12) 0.92213(11) 0.0286(3) Uani 1 1 d . . . . .
C8 C 0.47203(19) 0.73735(12) 0.29215(11) 0.0280(3) Uani 1 1 d . . . . .
C7 C 0.7013(2) 0.75800(12) 0.07997(11) 0.0304(3) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N4 C3 1.3375(19) . ?
N4 C4 1.3224(18) . ?
N13 C5 1.335(2) . ?
N13 C8 1.3215(18) . ?
N10 H10A 0.8800 . ?
N10 H10B 0.8800 . ?
N10 C5 1.3172(17) . ?
N2 N3 1.3362(18) . ?
N2 C2 1.3188(18) . ?
N5 H5A 0.8800 . ?
N5 H5B 0.8800 . ?
N5 C3 1.3154(18) . ?
N3 C4 1.3433(19) . ?
N11 N12 1.3292(19) . ?
N11 C6 1.3208(18) . ?
N12 C8 1.3451(19) . ?
N7 N6 1.2610(19) . ?
N7 N8 1.110(2) . ?
N14 N15 1.2626(19) . ?
N14 C8 1.3880(19) . ?
N15 N16 1.1136(19) . ?
N1 C1 1.1410(18) . ?
N6 C4 1.392(2) . ?
N9 C7 1.1410(19) . ?
C3 C2 1.4364(19) . ?
C5 C6 1.4328(19) . ?
C2 C1 1.428(2) . ?
C6 C7 1.430(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C4 N4 C3 115.75(12) . . ?
C8 N13 C5 115.82(12) . . ?
H10A N10 H10B 120.0 . . ?
C5 N10 H10A 120.0 . . ?
C5 N10 H10B 120.0 . . ?
C2 N2 N3 119.26(12) . . ?
H5A N5 H5B 120.0 . . ?
C3 N5 H5A 120.0 . . ?
C3 N5 H5B 120.0 . . ?
N2 N3 C4 116.79(12) . . ?
C6 N11 N12 119.31(12) . . ?
N11 N12 C8 116.66(12) . . ?
N8 N7 N6 172.63(16) . . ?
N15 N14 C8 112.88(12) . . ?
N16 N15 N14 172.16(16) . . ?
N7 N6 C4 113.19(12) . . ?
N4 C3 C2 117.97(12) . . ?
N5 C3 N4 118.81(12) . . ?
N5 C3 C2 123.22(13) . . ?
N13 C5 C6 117.77(12) . . ?
N10 C5 N13 118.88(12) . . ?
N10 C5 C6 123.34(13) . . ?
N2 C2 C3 122.13(13) . . ?
N2 C2 C1 116.92(12) . . ?
C1 C2 C3 120.95(13) . . ?
N11 C6 C5 122.28(13) . . ?
N11 C6 C7 116.72(13) . . ?
C7 C6 C5 120.99(12) . . ?
N4 C4 N3 128.10(14) . . ?
N4 C4 N6 120.20(13) . . ?
N3 C4 N6 111.70(12) . . ?
N1 C1 C2 176.96(15) . . ?
N13 C8 N12 128.11(14) . . ?
N13 C8 N14 120.22(13) . . ?
N12 C8 N14 111.66(12) . . ?
N9 C7 C6 176.97(15) . . ?

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

data_2
_audit_block_doi                 10.5517/ccdc.csd.cc1ps6m9
_database_code_depnum_ccdc_archive 'CCDC 1572401'
_audit_update_record             
;
2017-09-04 deposited with the CCDC.	2019-04-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'H4 N O, C4 H2 N11, 2(H2 O)'
_chemical_formula_sum            'C4 H10 N12 O3'
_chemical_formula_weight         274.24

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_H-M_alt        'C c'
_space_group_name_Hall           'C -2yc'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'x, -y, z+1/2'
'x+1/2, y+1/2, z'
'x+1/2, -y+1/2, z+1/2'

_cell_length_a                   5.9556(6)
_cell_length_b                   27.800(3)
_cell_length_c                   6.8014(6)
_cell_angle_alpha                90
_cell_angle_beta                 98.966(3)
_cell_angle_gamma                90
_cell_volume                     1112.31(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    2233
_cell_measurement_theta_min      2.93
_cell_measurement_theta_max      26.23

_exptl_crystal_description       plate
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.638
_exptl_crystal_F_000             568
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.360
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    0.138
_shelx_estimated_absorpt_T_min   0.952
_shelx_estimated_absorpt_T_max   0.989
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6992
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_process_details   'SADABS (Bruker, 2014)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'PHOTON 100 CMOS detector'
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6558
_diffrn_reflns_av_unetI/netI     0.0806
_diffrn_reflns_av_R_equivalents  0.0531
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_k_max       34
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         2.931
_diffrn_reflns_theta_max         26.361
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             2235
_reflns_number_gt                1604
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.954
_reflns_Friedel_fraction_max     0.961
_reflns_Friedel_fraction_full    0.985

_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.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0331P)²+0.3783P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 607 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.3(10)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2235
_refine_ls_number_parameters     202
_refine_ls_number_restraints     19
_refine_ls_R_factor_all          0.0905
_refine_ls_R_factor_gt           0.0490
_refine_ls_wR_factor_ref         0.0869
_refine_ls_wR_factor_gt          0.0767
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_restrained_S_all      1.037
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
C1 C 0.4402(7) 0.38752(16) 0.9436(7) 0.0158(11) Uani 1 1 d . . . . .
C2 C 0.6215(8) 0.45706(17) 1.0328(7) 0.0163(12) Uani 1 1 d . . . . .
C3 C 0.4148(9) 0.48288(15) 0.9370(7) 0.0139(10) Uani 1 1 d . . . . .
C4 C 0.4022(8) 0.53552(15) 0.9320(7) 0.0132(10) Uani 1 1 d . . . . .
N1 N 0.3938(7) 0.34104(12) 0.9178(6) 0.0203(9) Uani 1 1 d . . . . .
N2 N 0.1752(7) 0.33914(14) 0.8177(6) 0.0256(11) Uani 1 1 d . . . . .
N3 N 0.0855(7) 0.38144(14) 0.7820(6) 0.0213(10) Uani 1 1 d . . . . .
N4 N 0.2535(6) 0.41216(13) 0.8612(6) 0.0143(9) Uani 1 1 d . . . . .
N5 N 0.6288(6) 0.40921(14) 1.0349(6) 0.0176(9) Uani 1 1 d . . . . .
N6 N 0.2330(7) 0.46039(13) 0.8532(6) 0.0154(10) Uani 1 1 d . . . . .
N7 N 0.7992(7) 0.48157(15) 1.1182(6) 0.0181(10) Uani 1 1 d D . . . .
H7A H 0.785(9) 0.5121(10) 1.128(7) 0.022 Uiso 1 1 d D U . . .
H7B H 0.914(6) 0.4657(15) 1.182(7) 0.022 Uiso 1 1 d D U . . .
N8 N 0.5618(6) 0.56435(12) 1.0281(6) 0.0176(10) Uani 1 1 d . . . . .
N9 N 0.4834(6) 0.60894(14) 0.9851(6) 0.0178(10) Uani 1 1 d . . . . .
N10 N 0.2848(7) 0.60629(13) 0.8677(6) 0.0190(10) Uani 1 1 d . . . . .
N11 N 0.2282(6) 0.56009(13) 0.8317(5) 0.0169(10) Uani 1 1 d . . . . .
N12 N 0.8428(7) 0.72899(13) 0.4155(6) 0.0215(10) Uani 1 1 d D . . . .
H12A H 0.895(6) 0.7046(11) 0.510(5) 0.032 Uiso 1 1 d D U . . .
H12B H 0.949(5) 0.7548(12) 0.427(5) 0.032 Uiso 1 1 d D U . . .
H12C H 0.826(6) 0.7161(12) 0.284(4) 0.032 Uiso 1 1 d D U . . .
O1 O 0.6277(6) 0.74569(12) 0.4526(6) 0.0317(9) Uani 1 1 d D . . . .
H1D H 0.556(9) 0.7194(13) 0.456(8) 0.038 Uiso 1 1 d D U . . .
O2 O 0.9148(6) 0.66423(11) 0.7204(5) 0.0207(8) Uani 1 1 d D . . . .
H2D H 1.039(6) 0.6524(15) 0.776(7) 0.025 Uiso 1 1 d D U . . .
H2E H 0.846(7) 0.6411(13) 0.668(7) 0.025 Uiso 1 1 d D U . . .
O3 O 0.6796(6) 0.70053(11) 1.0182(5) 0.0220(8) Uani 1 1 d D . . . .
H3D H 0.773(7) 0.6965(16) 0.943(6) 0.026 Uiso 1 1 d D U . . .
H3E H 0.628(8) 0.6740(12) 1.036(8) 0.026 Uiso 1 1 d D 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
C1 N1 1.327(5) . ?
C1 N5 1.339(6) . ?
C1 N4 1.351(6) . ?
C2 N7 1.315(6) . ?
C2 N5 1.331(6) . ?
C2 C3 1.485(6) . ?
C3 N6 1.302(6) . ?
C3 C4 1.465(6) . ?
C4 N8 1.334(5) . ?
C4 N11 1.336(5) . ?
N1 N2 1.373(5) . ?
N2 N3 1.299(5) . ?
N3 N4 1.361(5) . ?
N4 N6 1.347(5) . ?
N7 H7A 0.86(3) . ?
N7 H7B 0.87(3) . ?
N8 N9 1.341(5) . ?
N9 N10 1.322(5) . ?
N10 N11 1.341(5) . ?
N12 O1 1.422(5) . ?
N12 H12A 0.95(3) . ?
N12 H12B 0.95(3) . ?
N12 H12C 0.95(3) . ?
O1 H1D 0.85(3) . ?
O2 H2D 0.84(3) . ?
O2 H2E 0.81(3) . ?
O3 H3D 0.82(3) . ?
O3 H3E 0.82(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 N5 129.9(4) . . ?
N1 C1 N4 107.3(4) . . ?
N5 C1 N4 122.7(4) . . ?
N7 C2 N5 119.4(4) . . ?
N7 C2 C3 119.9(4) . . ?
N5 C2 C3 120.8(4) . . ?
N6 C3 C4 115.7(4) . . ?
N6 C3 C2 122.4(4) . . ?
C4 C3 C2 121.9(4) . . ?
N8 C4 N11 112.3(3) . . ?
N8 C4 C3 124.0(4) . . ?
N11 C4 C3 123.7(4) . . ?
C1 N1 N2 105.3(4) . . ?
N3 N2 N1 112.9(3) . . ?
N2 N3 N4 103.8(4) . . ?
N6 N4 C1 125.8(4) . . ?
N6 N4 N3 123.6(4) . . ?
C1 N4 N3 110.6(3) . . ?
C2 N5 C1 114.9(4) . . ?
C3 N6 N4 113.4(4) . . ?
C2 N7 H7A 118(4) . . ?
C2 N7 H7B 118(3) . . ?
H7A N7 H7B 123(5) . . ?
C4 N8 N9 104.6(3) . . ?
N10 N9 N8 109.2(4) . . ?
N9 N10 N11 109.8(4) . . ?
C4 N11 N10 104.1(3) . . ?
O1 N12 H12A 109(2) . . ?
O1 N12 H12B 110(2) . . ?
H12A N12 H12B 110(2) . . ?
O1 N12 H12C 109(2) . . ?
H12A N12 H12C 110(3) . . ?
H12B N12 H12C 110(3) . . ?
N12 O1 H1D 101(4) . . ?
H2D O2 H2E 104(4) . . ?
H3D O3 H3E 106(4) . . ?

_refine_diff_density_max         0.289
_refine_diff_density_min         -0.361
_refine_diff_density_rms         0.074

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

data_mo_2017354-136_0m
_audit_block_doi                 10.5517/ccdc.csd.cc1ps6l8
_database_code_depnum_ccdc_archive 'CCDC 1572400'
_audit_update_record             
;
2017-09-04 deposited with the CCDC.	2019-04-26 downloaded from the CCDC.
;
_audit_creation_date             2017-05-10
_audit_creation_method           
;
Olex2 1.2-alpha
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5335)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C H4 O, C4 H3 N11'
_chemical_formula_sum            'C5 H7 N11 O'
_chemical_formula_weight         237.22
_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/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   6.8713(14)
_cell_length_b                   8.9648(19)
_cell_length_c                   16.596(4)
_cell_angle_alpha                90
_cell_angle_beta                 93.027(4)
_cell_angle_gamma                90
_cell_volume                     1020.9(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2453
_cell_measurement_temperature    173
_cell_measurement_theta_max      27.04
_cell_measurement_theta_min      2.46
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.121
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6605
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2008/1 (Bruker,2008) was used for absorption correction. wR2(int) was 0.0921 before and 0.0460 after correction. The Ratio of minimum to maximum transmission is 0.8859. The λ/2 correction factor is 0.0015.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.543
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             488
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0309
_diffrn_reflns_av_unetI/netI     0.0302
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            7378
_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         27.513
_diffrn_reflns_theta_min         2.458
_diffrn_ambient_temperature      173
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_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                1905
_reflns_number_total             2335
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.224
_refine_diff_density_min         -0.261
_refine_diff_density_rms         0.063
_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     160
_refine_ls_number_reflns         2335
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0489
_refine_ls_R_factor_gt           0.0396
_refine_ls_restrained_S_all      1.043
_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)+(0.0620P)²+0.1270P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1022
_refine_ls_wR_factor_ref         0.1090
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a X=CH2 refined with riding coordinates:
 N00A(H00A,H00B)
2.b Idealised Me refined as rotating group:
 C00H(H00C,H00D,H00E)
2.c Idealised tetrahedral OH refined as rotating group:
 O001(H001)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
_atom_sites_special_details      
;
The structure was solved using Direct Methods (ShelXS). RE = 0.2, Nqual =  -1, Ralpha = 0.035
;
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 0.46600(14) 0.24621(13) 0.55790(6) 0.0383(3) Uani 1 1 d . . . . .
H001 H 0.5050 0.2358 0.5111 0.057 Uiso 1 1 calc GR . . . .
N002 N 0.25702(14) 0.29579(13) 0.79596(6) 0.0226(2) Uani 1 1 d . . . . .
N003 N 0.40234(15) 0.32975(12) 0.74841(6) 0.0233(2) Uani 1 1 d . . . . .
N004 N 0.71319(16) 0.39715(14) 0.65792(7) 0.0263(3) Uani 1 1 d . . . . .
N005 N 0.39347(15) 0.40552(14) 0.91538(6) 0.0276(3) Uani 1 1 d . . . . .
N006 N 0.85989(16) 0.52134(13) 0.75562(7) 0.0295(3) Uani 1 1 d . . . . .
N007 N 0.08727(16) 0.27338(14) 0.90115(7) 0.0315(3) Uani 1 1 d . . . . .
N008 N 0.09500(16) 0.21663(14) 0.77165(7) 0.0296(3) Uani 1 1 d . . . . .
N009 N -0.00335(17) 0.20548(15) 0.83592(7) 0.0330(3) Uani 1 1 d . . . . .
N00A N 0.68971(17) 0.51942(15) 0.90658(7) 0.0321(3) Uani 1 1 d . . . . .
H00A H 0.6878 0.5441 0.9579 0.039 Uiso 1 1 calc R . . . .
H00B H 0.7893 0.5452 0.8784 0.039 Uiso 1 1 calc R . . . .
N00B N 0.96295(17) 0.52944(15) 0.68757(8) 0.0352(3) Uani 1 1 d . . . . .
N00C N 0.87479(17) 0.45543(15) 0.62902(8) 0.0337(3) Uani 1 1 d . . . . .
C00D C 0.70577(18) 0.43915(15) 0.73515(8) 0.0229(3) Uani 1 1 d . . . . .
C00E C 0.54481(17) 0.40126(15) 0.78583(7) 0.0216(3) Uani 1 1 d . . . . .
C00F C 0.25114(18) 0.32932(16) 0.87528(7) 0.0243(3) Uani 1 1 d . . . . .
C00G C 0.54309(18) 0.44374(15) 0.87194(7) 0.0240(3) Uani 1 1 d . . . . .
C00H C 0.2715(2) 0.3035(2) 0.55327(10) 0.0473(5) Uani 1 1 d . . . . .
H00C H 0.2139 0.2893 0.4985 0.071 Uiso 1 1 calc GR . . . .
H00D H 0.2739 0.4101 0.5664 0.071 Uiso 1 1 calc GR . . . .
H00E H 0.1933 0.2504 0.5918 0.071 Uiso 1 1 calc GR . . . .
H004 H 0.624(3) 0.345(2) 0.6267(11) 0.046(5) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O001 H001 0.8400 . ?
O001 C00H 1.4302(18) . ?
N002 N003 1.3401(14) . ?
N002 N008 1.3632(15) . ?
N002 C00F 1.3531(17) . ?
N003 C00E 1.3003(17) . ?
N004 N00C 1.3388(16) . ?
N004 C00D 1.3394(17) . ?
N004 H004 0.915(19) . ?
N005 C00F 1.3406(17) . ?
N005 C00G 1.3313(17) . ?
N006 N00B 1.3662(16) . ?
N006 C00D 1.3197(18) . ?
N007 N009 1.3634(17) . ?
N007 C00F 1.3247(17) . ?
N008 N009 1.2964(17) . ?
N00A H00A 0.8800 . ?
N00A H00B 0.8800 . ?
N00A C00G 1.3209(17) . ?
N00B N00C 1.2998(18) . ?
C00D C00E 1.4644(17) . ?
C00E C00G 1.4795(17) . ?
C00H H00C 0.9800 . ?
C00H H00D 0.9800 . ?
C00H H00E 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
C00H O001 H001 109.5 . . ?
N003 N002 N008 124.49(11) . . ?
N003 N002 C00F 125.73(11) . . ?
C00F N002 N008 109.74(10) . . ?
C00E N003 N002 113.35(11) . . ?
N00C N004 C00D 107.90(11) . . ?
N00C N004 H004 123.0(11) . . ?
C00D N004 H004 128.9(11) . . ?
C00G N005 C00F 115.23(11) . . ?
C00D N006 N00B 105.12(11) . . ?
C00F N007 N009 105.79(11) . . ?
N009 N008 N002 104.46(11) . . ?
N008 N009 N007 112.51(11) . . ?
H00A N00A H00B 120.0 . . ?
C00G N00A H00A 120.0 . . ?
C00G N00A H00B 120.0 . . ?
N00C N00B N006 110.45(11) . . ?
N00B N00C N004 107.09(11) . . ?
N004 C00D C00E 123.54(12) . . ?
N006 C00D N004 109.43(11) . . ?
N006 C00D C00E 127.00(12) . . ?
N003 C00E C00D 114.35(11) . . ?
N003 C00E C00G 122.96(11) . . ?
C00D C00E C00G 122.68(11) . . ?
N005 C00F N002 122.53(11) . . ?
N007 C00F N002 107.50(11) . . ?
N007 C00F N005 129.97(12) . . ?
N005 C00G C00E 120.17(11) . . ?
N00A C00G N005 119.31(12) . . ?
N00A C00G C00E 120.52(11) . . ?
O001 C00H H00C 109.5 . . ?
O001 C00H H00D 109.5 . . ?
O001 C00H H00E 109.5 . . ?
H00C C00H H00D 109.5 . . ?
H00C C00H H00E 109.5 . . ?
H00D C00H H00E 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_1
_audit_block_doi                 10.5517/ccdc.csd.cc20f9g7
_database_code_depnum_ccdc_archive 'CCDC 1859828'
loop_
_audit_author_name
_audit_author_address
'qian wang'
;nanjing university of science and technology
China
;
_audit_update_record             
;
2018-08-02 deposited with the CCDC.	2019-04-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C5 H2 N8 O2, C H4 O, H2 O'
_chemical_formula_sum            'C6 H8 N8 O4'
_chemical_formula_weight         256.20

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   6.2321(8)
_cell_length_b                   5.9535(7)
_cell_length_c                   29.279(4)
_cell_angle_alpha                90
_cell_angle_beta                 93.811(5)
_cell_angle_gamma                90
_cell_volume                     1083.9(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    172(2)
_cell_measurement_reflns_used    1385
_cell_measurement_theta_min      2.79
_cell_measurement_theta_max      25.32

_exptl_crystal_description       column
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.570
_exptl_crystal_F_000             528
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.110
_exptl_absorpt_coefficient_mu    0.133
_shelx_estimated_absorpt_T_min   0.969
_shelx_estimated_absorpt_T_max   0.986
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6419
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_process_details   'SADABS (Bruker, 2014)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      172(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'PHOTON 100 CMOS detector'
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6135
_diffrn_reflns_av_unetI/netI     0.0645
_diffrn_reflns_av_R_equivalents  0.0661
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_theta_min         2.789
_diffrn_reflns_theta_max         25.349
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             1982
_reflns_number_gt                1356
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0365P)²+0.8398P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1982
_refine_ls_number_parameters     179
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0949
_refine_ls_R_factor_gt           0.0530
_refine_ls_wR_factor_ref         0.1095
_refine_ls_wR_factor_gt          0.0959
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.041
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
C1 C 0.0415(4) 0.9475(5) 0.16923(9) 0.0193(6) Uani 1 1 d . . . . .
C2 C 0.1363(4) 1.1702(5) 0.12019(9) 0.0201(6) Uani 1 1 d . . . . .
C3 C 0.4628(4) 1.1557(5) 0.06813(9) 0.0203(6) Uani 1 1 d . . . . .
C4 C 0.4494(4) 0.9710(5) 0.09856(9) 0.0181(6) Uani 1 1 d . . . . .
C5 C 0.6345(5) 1.1645(5) 0.03764(10) 0.0236(7) Uani 1 1 d . . . . .
C6 C -0.5049(5) 0.8979(5) 0.29571(10) 0.0290(7) Uani 1 1 d . . . . .
H6A H -0.3924 1.0112 0.2929 0.044 Uiso 1 1 calc R U . . .
H6B H -0.6184 0.9198 0.2713 0.044 Uiso 1 1 calc R U . . .
H6C H -0.4428 0.7476 0.2931 0.044 Uiso 1 1 calc R U . . .
N1 N -0.0201(3) 1.1410(4) 0.14892(8) 0.0218(6) Uani 1 1 d . . . . .
N2 N 0.2178(3) 0.8468(4) 0.15753(7) 0.0209(6) Uani 1 1 d . . . . .
N3 N 0.2796(3) 0.9955(4) 0.12531(7) 0.0173(5) Uani 1 1 d . . . . .
N4 N 0.1588(4) 1.3386(4) 0.09037(8) 0.0242(6) Uani 1 1 d . . . . .
N5 N 0.3249(4) 1.3269(4) 0.06466(8) 0.0233(6) Uani 1 1 d . . . . .
N6 N -0.0875(4) 0.8446(4) 0.20355(8) 0.0244(6) Uani 1 1 d . . . . .
N7 N 0.7716(4) 1.1674(5) 0.01357(9) 0.0354(7) Uani 1 1 d . . . . .
N8 N 0.5753(4) 0.7968(4) 0.10265(8) 0.0218(6) Uani 1 1 d D . . . .
H8A H 0.551(4) 0.686(4) 0.1238(8) 0.026 Uiso 1 1 d D U . . .
H8B H 0.696(4) 0.791(5) 0.0852(9) 0.026 Uiso 1 1 d D U . . .
O1 O -0.2698(3) 0.9161(3) 0.20621(7) 0.0302(5) Uani 1 1 d . . . . .
O2 O -0.0043(3) 0.6932(4) 0.22658(7) 0.0381(6) Uani 1 1 d . . . . .
O3 O 0.0452(3) 0.2423(4) 0.43646(7) 0.0317(6) Uani 1 1 d D . . . .
H3C H -0.011(5) 0.118(4) 0.4288(10) 0.038 Uiso 1 1 d D U . . .
H3D H 0.002(5) 0.272(5) 0.4628(8) 0.038 Uiso 1 1 d D U . . .
O4 O -0.5943(3) 0.9200(4) 0.33937(7) 0.0292(5) Uani 1 1 d D . . . .
H4C H -0.711(4) 0.850(5) 0.3399(10) 0.035 Uiso 1 1 d D 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
C1 N2 1.317(3) . ?
C1 N1 1.341(3) . ?
C1 N6 1.462(3) . ?
C2 N1 1.340(3) . ?
C2 N4 1.343(3) . ?
C2 N3 1.372(3) . ?
C3 N5 1.333(3) . ?
C3 C4 1.421(4) . ?
C3 C5 1.439(4) . ?
C4 N8 1.301(3) . ?
C4 N3 1.365(3) . ?
C5 N7 1.143(4) . ?
C6 O4 1.434(3) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
N2 N3 1.367(3) . ?
N4 N5 1.322(3) . ?
N6 O2 1.220(3) . ?
N6 O1 1.221(3) . ?
N8 H8A 0.93(2) . ?
N8 H8B 0.94(2) . ?
O3 H3C 0.84(2) . ?
O3 H3D 0.85(2) . ?
O4 H4C 0.84(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 C1 N1 119.6(2) . . ?
N2 C1 N6 119.6(2) . . ?
N1 C1 N6 120.7(2) . . ?
N1 C2 N4 128.1(2) . . ?
N1 C2 N3 109.2(2) . . ?
N4 C2 N3 122.8(2) . . ?
N5 C3 C4 125.1(2) . . ?
N5 C3 C5 115.3(2) . . ?
C4 C3 C5 119.6(2) . . ?
N8 C4 N3 121.2(3) . . ?
N8 C4 C3 127.9(2) . . ?
N3 C4 C3 110.9(2) . . ?
N7 C5 C3 178.8(3) . . ?
O4 C6 H6A 109.5 . . ?
O4 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
O4 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C2 N1 C1 101.0(2) . . ?
C1 N2 N3 99.4(2) . . ?
C4 N3 N2 126.2(2) . . ?
C4 N3 C2 122.8(2) . . ?
N2 N3 C2 110.8(2) . . ?
N5 N4 C2 116.8(2) . . ?
N4 N5 C3 121.5(2) . . ?
O2 N6 O1 125.8(2) . . ?
O2 N6 C1 117.2(2) . . ?
O1 N6 C1 117.0(2) . . ?
C4 N8 H8A 120.4(18) . . ?
C4 N8 H8B 118.7(18) . . ?
H8A N8 H8B 121(3) . . ?
H3C O3 H3D 106(3) . . ?
C6 O4 H4C 111(2) . . ?

_refine_diff_density_max         0.230
_refine_diff_density_min         -0.267
_refine_diff_density_rms         0.061

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

data_1_CCDC1
_audit_block_doi                 10.5517/ccdc.csd.cc20f9j9
_database_code_depnum_ccdc_archive 'CCDC 1859830'
loop_
_audit_author_name
_audit_author_address
'qian wang'
;nanjing university of science and technology
China
;
_audit_update_record             
;
2018-08-02 deposited with the CCDC.	2019-04-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C5 H3 N11 O2, C2 H6 O'
_chemical_formula_sum            'C7 H9 N11 O3'
_chemical_formula_weight         295.25

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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           62
_space_group_name_H-M_alt        'P n m a'
_space_group_name_Hall           '-P 2ac 2n'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z'
'x+1/2, -y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z'
'-x-1/2, y-1/2, z-1/2'

_cell_length_a                   27.752(5)
_cell_length_b                   6.2922(14)
_cell_length_c                   6.9744(16)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1217.9(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    758
_cell_measurement_theta_min      3.01
_cell_measurement_theta_max      23.78

_exptl_crystal_description       needle
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.610
_exptl_crystal_F_000             608
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.090
_exptl_crystal_size_min          0.070
_exptl_absorpt_coefficient_mu    0.131
_shelx_estimated_absorpt_T_min   0.973
_shelx_estimated_absorpt_T_max   0.991
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5811
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_process_details   'SADABS (Bruker, 2014)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'PHOTON 100 CMOS detector'
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4659
_diffrn_reflns_av_unetI/netI     0.0554
_diffrn_reflns_av_R_equivalents  0.0774
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_h_max       33
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         2.936
_diffrn_reflns_theta_max         25.346
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             1229
_reflns_number_gt                761
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0655P)²+3.0145P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1229
_refine_ls_number_parameters     134
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.1279
_refine_ls_R_factor_gt           0.0721
_refine_ls_wR_factor_ref         0.1852
_refine_ls_wR_factor_gt          0.1555
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_restrained_S_all      1.059
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
C1 C 0.39997(19) 0.7500 0.4914(9) 0.0296(15) Uani 1 2 d S T P . .
C2 C 0.32618(19) 0.7500 0.4461(8) 0.0195(12) Uani 1 2 d S T P . .
C3 C 0.2540(2) 0.7500 0.6910(8) 0.0231(13) Uani 1 2 d S T P . .
C4 C 0.30051(19) 0.7500 0.7753(8) 0.0239(13) Uani 1 2 d S T P . .
C5 C 0.2118(2) 0.7500 0.8132(8) 0.0225(13) Uani 1 2 d S T P . .
N1 N 0.36791(17) 0.7500 0.3469(7) 0.0266(12) Uani 1 2 d S T P . .
N3 N 0.33619(16) 0.7500 0.6388(6) 0.0228(11) Uani 1 2 d S T P . .
N4 N 0.28125(16) 0.7500 0.3742(6) 0.0245(12) Uani 1 2 d S T P . .
N5 N 0.24619(15) 0.7500 0.5017(6) 0.0202(11) Uani 1 2 d S T P . .
N6 N 0.4515(2) 0.7500 0.4556(9) 0.0499(17) Uani 1 2 d S T P . .
N7 N 0.16598(17) 0.7500 0.7520(7) 0.0259(12) Uani 1 2 d DS T P . .
H7D H 0.1528(19) 0.7500 0.639(6) 0.031 Uiso 1 2 d DS U P . .
N8 N 0.13706(17) 0.7500 0.9068(7) 0.0295(13) Uani 1 2 d S T P . .
N9 N 0.16512(17) 0.7500 1.0565(7) 0.0280(12) Uani 1 2 d S T P . .
N10 N 0.21286(17) 0.7500 1.0042(7) 0.0264(11) Uani 1 2 d S T P . .
N11 N 0.31240(16) 0.7500 0.9588(7) 0.0266(12) Uani 1 2 d DS T P . .
H11D H 0.2870(16) 0.7500 1.032(8) 0.032 Uiso 1 2 d DS U P . .
H11E H 0.3422(13) 0.7500 0.992(9) 0.032 Uiso 1 2 d DS U P . .
N2A N 0.38438(16) 0.7500 0.6727(7) 0.0294(13) Uani 1 2 d S T P . .
O1 O 0.4642(2) 0.6943(11) 0.2943(10) 0.053(2) Uiso 0.5 1 d . . P . .
O2 O 0.4785(2) 0.786(8) 0.5894(9) 0.063(10) Uani 0.5 1 d . . P . .
O3 O 0.12522(17) 0.700(2) 0.4224(8) 0.043(4) Uani 0.5 1 d . . P A -1
H3 H 0.1384 0.7149 0.3133 0.051 Uiso 0.5 1 d R U P A -1
C6 C 0.0738(3) 0.7034(14) 0.3980(12) 0.034(2) Uiso 0.5 1 d . . P A -1
H6A H 0.0611 0.5575 0.4136 0.041 Uiso 0.5 1 calc R U P A -1
H6B H 0.0662 0.7510 0.2661 0.041 Uiso 0.5 1 calc R U P A -1
C7 C 0.0495(4) 0.8462(18) 0.5371(17) 0.068(3) Uiso 0.5 1 d . . P A -1
H7A H 0.0570 0.8001 0.6680 0.102 Uiso 0.5 1 calc R U P A -1
H7B H 0.0146 0.8406 0.5169 0.102 Uiso 0.5 1 calc R U P A -1
H7C H 0.0609 0.9921 0.5184 0.102 Uiso 0.5 1 calc R U P A -1


_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
C1 N2A 1.336(8) . ?
C1 N1 1.344(8) . ?
C1 N6 1.451(7) . ?
C2 N1 1.349(7) . ?
C2 N4 1.344(7) . ?
C2 N3 1.372(7) . ?
C3 N5 1.338(7) . ?
C3 C4 1.418(8) . ?
C3 C5 1.448(8) . ?
C4 N11 1.322(7) . ?
C4 N3 1.373(7) . ?
C5 N10 1.332(7) . ?
C5 N7 1.342(7) . ?
N3 N2A 1.358(6) . ?
N4 N5 1.318(6) . ?
N6 O2 1.219(13) 7_575 ?
N6 O2 1.219(13) . ?
N6 O1 1.230(8) 7_575 ?
N6 O1 1.230(8) . ?
N7 N8 1.345(7) . ?
N7 H7D 0.87(4) . ?
N8 N9 1.302(7) . ?
N9 N10 1.374(7) . ?
N11 H11D 0.87(3) . ?
N11 H11E 0.86(3) . ?
O1 O1 0.701(14) 7_575 ?
O2 O2 0.46(10) 7_575 ?
O3 C6 1.437(8) . ?
O3 H3 0.8500 . ?
C6 C7 1.484(13) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
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
N2A C1 N1 119.7(5) . . ?
N2A C1 N6 118.8(5) . . ?
N1 C1 N6 121.5(6) . . ?
N1 C2 N4 127.2(5) . . ?
N1 C2 N3 109.2(5) . . ?
N4 C2 N3 123.6(5) . . ?
N5 C3 C4 123.8(5) . . ?
N5 C3 C5 116.7(5) . . ?
C4 C3 C5 119.5(5) . . ?
N11 C4 N3 119.4(5) . . ?
N11 C4 C3 128.9(5) . . ?
N3 C4 C3 111.6(5) . . ?
N10 C5 N7 109.8(5) . . ?
N10 C5 C3 124.8(5) . . ?
N7 C5 C3 125.4(5) . . ?
C2 N1 C1 100.6(5) . . ?
N2A N3 C2 111.7(4) . . ?
N2A N3 C4 126.1(5) . . ?
C2 N3 C4 122.2(5) . . ?
N5 N4 C2 115.7(4) . . ?
N4 N5 C3 123.1(5) . . ?
O2 N6 O2 22(5) 7_575 . ?
O2 N6 O1 125.2(8) 7_575 7_575 ?
O2 N6 O1 118.0(12) . 7_575 ?
O2 N6 O1 118.0(12) 7_575 . ?
O2 N6 O1 125.2(8) . . ?
O1 N6 O1 33.1(7) 7_575 . ?
O2 N6 C1 118.3(6) 7_575 . ?
O2 N6 C1 118.3(6) . . ?
O1 N6 C1 116.2(6) 7_575 . ?
O1 N6 C1 116.2(6) . . ?
N8 N7 C5 108.1(5) . . ?
N8 N7 H7D 118(4) . . ?
C5 N7 H7D 133(4) . . ?
N9 N8 N7 106.7(4) . . ?
N8 N9 N10 111.3(4) . . ?
C5 N10 N9 104.2(5) . . ?
C4 N11 H11D 112(4) . . ?
C4 N11 H11E 120(4) . . ?
H11D N11 H11E 128(6) . . ?
C1 N2A N3 98.9(4) . . ?
O1 O1 N6 73.4(3) 7_575 . ?
O2 O2 N6 79(2) 7_575 . ?
C6 O3 H3 108.7 . . ?
O3 C6 C7 112.5(8) . . ?
O3 C6 H6A 109.1 . . ?
C7 C6 H6A 109.1 . . ?
O3 C6 H6B 109.1 . . ?
C7 C6 H6B 109.1 . . ?
H6A C6 H6B 107.8 . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?

_refine_diff_density_max         0.402
_refine_diff_density_min         -0.480
_refine_diff_density_rms         0.104

