# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 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_20180631-yc-44_0m
_database_code_depnum_ccdc_archive 'CCDC 1891351'
loop_
_audit_author_name
_audit_author_address
'Chao Yan'
;School of Chemical Engineering, Nanjing University of Science and Technology
China
;
_audit_update_record             
;
2019-05-15 deposited with the CCDC.	2019-06-06 downloaded from the CCDC.
;
_audit_creation_date             2018-06-23
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2016.07.08 svn.r3312 for OlexSys, GUI svn.r5203)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C5 H5 N7 O8'
_chemical_formula_sum            'C5 H5 N7 O8'
_chemical_formula_weight         291.16
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   11.757(3)
_cell_length_b                   12.706(3)
_cell_length_c                   13.594(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2030.8(8)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    922
_cell_measurement_temperature    173
_cell_measurement_theta_max      20.872
_cell_measurement_theta_min      2.997
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.180
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.6425
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0810 before and 0.0653 after correction.
The Ratio of minimum to maximum transmission is 0.8618.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear whiteish colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.905
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1184
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0788
_diffrn_reflns_av_unetI/netI     0.0683
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            11814
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.415
_diffrn_reflns_theta_min         2.796
_diffrn_ambient_temperature      173
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1512
_reflns_number_total             2285
_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       'Bruker APEX 3'
_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         0.253
_refine_diff_density_min         -0.316
_refine_diff_density_rms         0.066
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         2285
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0818
_refine_ls_R_factor_gt           0.0496
_refine_ls_restrained_S_all      1.040
_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)+(0.0449P)²+0.4829P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1081
_refine_ls_wR_factor_ref         0.1246
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups, All N(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B)
2.b Aromatic/amide H refined with riding coordinates:
 N5(H5), N4(H4), N3(H3)
;
_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
O5 O 0.51471(14) 0.21963(15) 0.59769(12) 0.0326(5) Uani 1 1 d . . . . .
O6 O 0.37560(15) 0.11587(16) 0.56324(13) 0.0384(5) Uani 1 1 d . . . . .
O8 O 0.42087(16) 0.13113(15) 0.28390(12) 0.0384(5) Uani 1 1 d . . . . .
O7 O 0.40399(16) 0.01800(14) 0.40133(14) 0.0370(5) Uani 1 1 d . . . . .
O1 O 0.65901(17) 0.39098(16) 0.64019(13) 0.0389(5) Uani 1 1 d . . . . .
N5 N 0.61233(15) 0.32581(15) 0.46174(13) 0.0202(4) Uani 1 1 d . . . . .
H5 H 0.6281 0.3035 0.5215 0.024 Uiso 1 1 calc R . . . .
N6 N 0.45662(16) 0.16966(16) 0.53716(14) 0.0235(5) Uani 1 1 d . . . . .
O3 O 0.73527(17) 0.66272(15) 0.55172(15) 0.0438(5) Uani 1 1 d . . . . .
N4 N 0.57236(16) 0.27748(15) 0.30459(13) 0.0229(5) Uani 1 1 d . . . . .
H4 H 0.5295 0.2471 0.2598 0.027 Uiso 1 1 calc R . . . .
N7 N 0.43338(16) 0.10485(17) 0.37109(15) 0.0253(5) Uani 1 1 d . . . . .
N3 N 0.65757(16) 0.44047(17) 0.34006(14) 0.0251(5) Uani 1 1 d . . . . .
H3 H 0.6623 0.5045 0.3156 0.030 Uiso 1 1 calc R . . . .
O2 O 0.60847(18) 0.55236(17) 0.66489(15) 0.0507(6) Uani 1 1 d . . . . .
O4 O 0.7130(2) 0.62762(16) 0.39690(15) 0.0551(7) Uani 1 1 d . . . . .
N1 N 0.64069(17) 0.48180(18) 0.61029(16) 0.0293(5) Uani 1 1 d . . . . .
N2 N 0.70347(18) 0.60324(17) 0.48544(16) 0.0312(5) Uani 1 1 d . . . . .
C4 C 0.55594(18) 0.25979(18) 0.39839(16) 0.0184(5) Uani 1 1 d . . . . .
C2 C 0.64492(18) 0.42563(18) 0.43491(17) 0.0209(5) Uani 1 1 d . . . . .
C5 C 0.48477(18) 0.17862(18) 0.43604(16) 0.0204(5) Uani 1 1 d . . . . .
C1 C 0.65734(19) 0.50380(19) 0.50796(17) 0.0229(5) Uani 1 1 d . . . . .
C3 C 0.6637(2) 0.3490(2) 0.27636(17) 0.0272(6) Uani 1 1 d . . . . .
H3A H 0.7383 0.3138 0.2838 0.033 Uiso 1 1 calc R . . . .
H3B H 0.6547 0.3704 0.2068 0.033 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O5 N6 1.244(2) . ?
O6 N6 1.225(2) . ?
O8 N7 1.240(3) . ?
O7 N7 1.227(3) . ?
O1 N1 1.242(3) . ?
N5 H5 0.8800 . ?
N5 C4 1.373(3) . ?
N5 C2 1.374(3) . ?
N6 C5 1.419(3) . ?
O3 N2 1.234(3) . ?
N4 H4 0.8800 . ?
N4 C4 1.309(3) . ?
N4 C3 1.458(3) . ?
N7 C5 1.422(3) . ?
N3 H3 0.8800 . ?
N3 C2 1.312(3) . ?
N3 C3 1.451(3) . ?
O2 N1 1.224(3) . ?
O4 N2 1.248(3) . ?
N1 C1 1.432(3) . ?
N2 C1 1.409(3) . ?
C4 C5 1.423(3) . ?
C2 C1 1.412(3) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?

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 H5 118.9 . . ?
C4 N5 C2 122.14(19) . . ?
C2 N5 H5 118.9 . . ?
O5 N6 C5 118.17(19) . . ?
O6 N6 O5 121.4(2) . . ?
O6 N6 C5 120.45(19) . . ?
C4 N4 H4 120.9 . . ?
C4 N4 C3 118.17(19) . . ?
C3 N4 H4 120.9 . . ?
O8 N7 C5 117.8(2) . . ?
O7 N7 O8 121.9(2) . . ?
O7 N7 C5 120.3(2) . . ?
C2 N3 H3 120.8 . . ?
C2 N3 C3 118.5(2) . . ?
C3 N3 H3 120.8 . . ?
O1 N1 C1 118.4(2) . . ?
O2 N1 O1 122.4(2) . . ?
O2 N1 C1 119.2(2) . . ?
O3 N2 O4 121.7(2) . . ?
O3 N2 C1 120.5(2) . . ?
O4 N2 C1 117.8(2) . . ?
N5 C4 C5 120.07(19) . . ?
N4 C4 N5 115.8(2) . . ?
N4 C4 C5 124.1(2) . . ?
N5 C2 C1 119.4(2) . . ?
N3 C2 N5 115.2(2) . . ?
N3 C2 C1 125.3(2) . . ?
N6 C5 N7 116.71(19) . . ?
N6 C5 C4 122.9(2) . . ?
N7 C5 C4 120.3(2) . . ?
N2 C1 N1 116.0(2) . . ?
N2 C1 C2 121.2(2) . . ?
C2 C1 N1 122.1(2) . . ?
N4 C3 H3A 110.1 . . ?
N4 C3 H3B 110.1 . . ?
N3 C3 N4 107.80(18) . . ?
N3 C3 H3A 110.1 . . ?
N3 C3 H3B 110.1 . . ?
H3A C3 H3B 108.5 . . ?

_shelx_SHELXL_version_number     2014/7
_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_mo_20180681-yx-48_0m
_database_code_depnum_ccdc_archive 'CCDC 1892962'
loop_
_audit_author_name
_audit_author_address
'Chao Yan'
;School of Chemical Engineering, Nanjing University of Science and Technology
China
;
_audit_update_record             
;
2019-05-15 deposited with the CCDC.	2019-06-06 downloaded from the CCDC.
;
_audit_creation_date             2019-02-26
_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         'C9 H14 N10 O8, H2 O'
_chemical_formula_sum            'C9 H16 N10 O9'
_chemical_formula_weight         408.32
_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                   17.038(4)
_cell_length_b                   7.1500(16)
_cell_length_c                   13.854(3)
_cell_angle_alpha                90
_cell_angle_beta                 99.084(6)
_cell_angle_gamma                90
_cell_volume                     1666.6(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    857
_cell_measurement_temperature    173
_cell_measurement_theta_max      21.191
_cell_measurement_theta_min      2.978
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.144
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6548
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0737 before and 0.0596 after correction.
The Ratio of minimum to maximum transmission is 0.8785.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear whiteish colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.627
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             848
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.18
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0892
_diffrn_reflns_av_unetI/netI     0.1024
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            11113
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.436
_diffrn_reflns_theta_min         1.210
_diffrn_ambient_temperature      173
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_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                1791
_reflns_number_total             3399
_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       'Bruker APEX 3'
_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    'SIR2004 (Burla et al.,  2007)'
_refine_diff_density_max         0.393
_refine_diff_density_min         -0.273
_refine_diff_density_rms         0.069
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     260
_refine_ls_number_reflns         3399
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.1333
_refine_ls_R_factor_gt           0.0563
_refine_ls_restrained_S_all      1.009
_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)+(0.0602P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1196
_refine_ls_wR_factor_ref         0.1541
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All O(H) groups
2. Restrained distances
 H9A-H7
 2.2 with sigma of 0.02
 H7-H9B
 2.2 with sigma of 0.02
3.a Free rotating group:
 O9(H9A)
3.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C6(H6A,H6B), C3(H3A,H3B), C5(H5A,H5B), C4(H4A,H4B)
3.c Aromatic/amide H refined with riding coordinates:
 N8(H8), N4(H4), N7(H7), N3(H3)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.39474(15) 0.5536(3) 0.60894(18) 0.0325(6) Uani 1 1 d . . . . .
O4 O 0.45383(15) 0.0066(3) 0.65172(18) 0.0354(6) Uani 1 1 d . . . . .
O2 O 0.52053(15) 0.5967(3) 0.60161(18) 0.0347(6) Uani 1 1 d . . . . .
O8 O 1.01776(15) 0.8376(4) 0.5631(2) 0.0438(7) Uani 1 1 d . . . . .
O5 O 0.81748(16) 0.8429(4) 0.73113(19) 0.0414(7) Uani 1 1 d . . . . .
N1 N 0.46338(17) 0.4930(4) 0.61240(19) 0.0254(7) Uani 1 1 d . . . . .
N8 N 0.90694(17) 0.5338(4) 0.6280(2) 0.0272(7) Uani 1 1 d . . . . .
H8 H 0.941483 0.528774 0.682358 0.033 Uiso 1 1 calc R . . . .
N4 N 0.58797(17) 0.1686(4) 0.5549(2) 0.0256(7) Uani 1 1 d . . . . .
H4 H 0.554057 0.154619 0.500509 0.031 Uiso 1 1 calc R . . . .
O7 O 1.02577(16) 1.0576(4) 0.67222(19) 0.0488(8) Uani 1 1 d . . . . .
N7 N 0.83172(17) 0.7105(4) 0.5112(2) 0.0261(7) Uani 1 1 d . . . . .
H7 H 0.816996 0.821348 0.487315 0.031 Uiso 1 1 calc DR . . . .
O6 O 0.90696(18) 1.0565(4) 0.7747(2) 0.0507(8) Uani 1 1 d . . . . .
N6 N 0.79767(17) 0.3863(4) 0.5275(2) 0.0293(7) Uani 1 1 d . . . . .
N9 N 0.87966(19) 0.9274(4) 0.7207(2) 0.0323(8) Uani 1 1 d . . . . .
N2 N 0.42659(19) 0.1713(4) 0.6410(2) 0.0323(8) Uani 1 1 d . . . . .
N5 N 0.72354(17) 0.2160(4) 0.6286(2) 0.0290(7) Uani 1 1 d . . . . .
N10 N 0.98887(18) 0.9240(4) 0.6274(2) 0.0323(8) Uani 1 1 d . . . . .
N3 N 0.61326(17) 0.2672(4) 0.7136(2) 0.0283(7) Uani 1 1 d . . . . .
H3 H 0.595613 0.315683 0.764494 0.034 Uiso 1 1 calc R . . . .
O3 O 0.35593(16) 0.2040(4) 0.6417(3) 0.0601(9) Uani 1 1 d . . . . .
C2 C 0.5643(2) 0.2458(5) 0.6322(2) 0.0225(8) Uani 1 1 d . . . . .
C8 C 0.8835(2) 0.6982(5) 0.5916(2) 0.0235(8) Uani 1 1 d . . . . .
C1 C 0.4813(2) 0.3054(5) 0.6262(2) 0.0248(8) Uani 1 1 d . . . . .
C9 C 0.9155(2) 0.8662(5) 0.6430(2) 0.0251(8) Uani 1 1 d . . . . .
C7 C 0.7978(2) 0.5411(5) 0.4601(2) 0.0296(9) Uani 1 1 d . . . . .
H7A H 0.742709 0.567075 0.428236 0.036 Uiso 1 1 calc R . . . .
H7B H 0.829384 0.506983 0.408566 0.036 Uiso 1 1 calc R . . . .
C6 C 0.8773(2) 0.3598(5) 0.5809(3) 0.0318(9) Uani 1 1 d . . . . .
H6A H 0.913204 0.318326 0.535446 0.038 Uiso 1 1 calc R . . . .
H6B H 0.876549 0.261285 0.631009 0.038 Uiso 1 1 calc R . . . .
C3 C 0.6975(2) 0.2121(6) 0.7228(3) 0.0349(9) Uani 1 1 d . . . . .
H3A H 0.730441 0.298884 0.767922 0.042 Uiso 1 1 calc R . . . .
H3B H 0.704442 0.084550 0.750563 0.042 Uiso 1 1 calc R . . . .
C5 C 0.7382(2) 0.4036(5) 0.5933(3) 0.0298(9) Uani 1 1 d . . . . .
H5A H 0.758221 0.486625 0.648919 0.036 Uiso 1 1 calc R . . . .
H5B H 0.688308 0.457519 0.557765 0.036 Uiso 1 1 calc R . . . .
C4 C 0.6708(2) 0.1057(5) 0.5595(3) 0.0323(9) Uani 1 1 d . . . . .
H4A H 0.675054 -0.027498 0.579028 0.039 Uiso 1 1 calc R . . . .
H4B H 0.686605 0.116974 0.493956 0.039 Uiso 1 1 calc R . . . .
O9 O 0.81310(16) 1.0470(4) 0.4084(2) 0.0450(8) Uani 1 1 d . . . . .
H9A H 0.834624 0.992610 0.362945 0.067 Uiso 1 1 d DG . . . .
H9B H 0.808(10) 1.120(7) 0.448(13) 0.47(11) 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
O1 N1 1.241(3) . ?
O4 N2 1.266(4) . ?
O2 N1 1.252(4) . ?
O8 N10 1.247(4) . ?
O5 N9 1.248(4) . ?
N1 C1 1.382(4) . ?
N8 H8 0.8800 . ?
N8 C8 1.317(4) . ?
N8 C6 1.458(4) . ?
N4 H4 0.8800 . ?
N4 C2 1.322(4) . ?
N4 C4 1.473(4) . ?
O7 N10 1.253(4) . ?
N7 H7 0.8800 . ?
N7 C8 1.311(4) . ?
N7 C7 1.473(4) . ?
O6 N9 1.232(4) . ?
N6 C7 1.448(4) . ?
N6 C6 1.452(5) . ?
N6 C5 1.472(4) . ?
N9 C9 1.389(4) . ?
N2 O3 1.228(4) . ?
N2 C1 1.375(4) . ?
N5 C3 1.443(4) . ?
N5 C5 1.462(4) . ?
N5 C4 1.441(5) . ?
N10 C9 1.367(4) . ?
N3 H3 0.8800 . ?
N3 C2 1.302(4) . ?
N3 C3 1.474(4) . ?
C2 C1 1.468(5) . ?
C8 C9 1.457(5) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
O9 H9A 0.8695 . ?
O9 H9B 0.77(16) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 N1 O2 122.3(3) . . ?
O1 N1 C1 122.0(3) . . ?
O2 N1 C1 115.7(3) . . ?
C8 N8 H8 119.1 . . ?
C8 N8 C6 121.9(3) . . ?
C6 N8 H8 119.1 . . ?
C2 N4 H4 119.8 . . ?
C2 N4 C4 120.3(3) . . ?
C4 N4 H4 119.8 . . ?
C8 N7 H7 119.5 . . ?
C8 N7 C7 120.9(3) . . ?
C7 N7 H7 119.5 . . ?
C7 N6 C6 109.4(3) . . ?
C7 N6 C5 114.0(3) . . ?
C6 N6 C5 112.0(3) . . ?
O5 N9 C9 114.9(3) . . ?
O6 N9 O5 122.6(3) . . ?
O6 N9 C9 122.5(3) . . ?
O4 N2 C1 115.0(3) . . ?
O3 N2 O4 121.2(3) . . ?
O3 N2 C1 123.8(3) . . ?
C3 N5 C5 114.4(3) . . ?
C4 N5 C3 110.0(3) . . ?
C4 N5 C5 113.6(3) . . ?
O8 N10 O7 120.5(3) . . ?
O8 N10 C9 116.0(3) . . ?
O7 N10 C9 123.5(3) . . ?
C2 N3 H3 119.2 . . ?
C2 N3 C3 121.7(3) . . ?
C3 N3 H3 119.2 . . ?
N4 C2 C1 119.3(3) . . ?
N3 C2 N4 121.0(3) . . ?
N3 C2 C1 119.7(3) . . ?
N8 C8 C9 118.8(3) . . ?
N7 C8 N8 120.5(3) . . ?
N7 C8 C9 120.7(3) . . ?
N1 C1 C2 118.6(3) . . ?
N2 C1 N1 123.9(3) . . ?
N2 C1 C2 117.3(3) . . ?
N9 C9 C8 117.5(3) . . ?
N10 C9 N9 123.5(3) . . ?
N10 C9 C8 116.9(3) . . ?
N7 C7 H7A 109.4 . . ?
N7 C7 H7B 109.4 . . ?
N6 C7 N7 111.1(3) . . ?
N6 C7 H7A 109.4 . . ?
N6 C7 H7B 109.4 . . ?
H7A C7 H7B 108.0 . . ?
N8 C6 H6A 109.6 . . ?
N8 C6 H6B 109.6 . . ?
N6 C6 N8 110.3(3) . . ?
N6 C6 H6A 109.6 . . ?
N6 C6 H6B 109.6 . . ?
H6A C6 H6B 108.1 . . ?
N5 C3 N3 110.6(3) . . ?
N5 C3 H3A 109.5 . . ?
N5 C3 H3B 109.5 . . ?
N3 C3 H3A 109.5 . . ?
N3 C3 H3B 109.5 . . ?
H3A C3 H3B 108.1 . . ?
N6 C5 H5A 110.2 . . ?
N6 C5 H5B 110.2 . . ?
N5 C5 N6 107.5(3) . . ?
N5 C5 H5A 110.2 . . ?
N5 C5 H5B 110.2 . . ?
H5A C5 H5B 108.5 . . ?
N4 C4 H4A 109.5 . . ?
N4 C4 H4B 109.5 . . ?
N5 C4 N4 110.8(3) . . ?
N5 C4 H4A 109.5 . . ?
N5 C4 H4B 109.5 . . ?
H4A C4 H4B 108.1 . . ?
H9A O9 H9B 157.6 . . ?

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

data_a
_database_code_depnum_ccdc_archive 'CCDC 1892969'
loop_
_audit_author_name
_audit_author_address
'Chao Yan'
;School of Chemical Engineering, Nanjing University of Science and Technology
China
;
_audit_update_record             
;
2019-05-15 deposited with the CCDC.	2019-06-06 downloaded from the CCDC.
;
_audit_creation_date             2019-02-26
_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         '4(C7 H14 Cl N2), 4(C5 H4 N7 O8), H2 O'
_chemical_formula_sum            'C48 H74 Cl4 N36 O33'
_chemical_formula_weight         1825.23
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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                   13.790(2)
_cell_length_b                   7.0973(11)
_cell_length_c                   19.700(3)
_cell_angle_alpha                90
_cell_angle_beta                 98.238(4)
_cell_angle_gamma                90
_cell_volume                     1908.3(5)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    1026
_cell_measurement_temperature    173
_cell_measurement_theta_max      20.488
_cell_measurement_theta_min      2.985
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.267
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.6499
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0656 before and 0.0514 after correction.
The Ratio of minimum to maximum transmission is 0.8718.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear whiteish colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.588
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             946
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.18
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0854
_diffrn_reflns_av_unetI/netI     0.0788
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            16374
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.404
_diffrn_reflns_theta_min         1.940
_diffrn_ambient_temperature      173
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2402
_reflns_number_total             4304
_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       'Bruker APEX 3'
_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         0.424
_refine_diff_density_min         -0.485
_refine_diff_density_rms         0.066
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     311
_refine_ls_number_reflns         4304
_refine_ls_number_restraints     54
_refine_ls_R_factor_all          0.1216
_refine_ls_R_factor_gt           0.0606
_refine_ls_restrained_S_all      1.018
_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)+(0.0663P)²+0.0748P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1345
_refine_ls_wR_factor_ref         0.1666
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All O(H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(O3A) \\sim Ueq, Uanis(N2A) \\sim Ueq, Uanis(O3) \\sim Ueq, Uanis(N2)
\\sim Ueq, Uanis(O4A) \\sim Ueq, Uanis(O4) \\sim Ueq: with sigma of 0.02 and
sigma for terminal atoms of 0.04
3. Rigid body (RIGU) restrains
 O3A, O3, N2A, N2, O4A, O4
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4. Others
 Sof(O3A)=Sof(N2A)=Sof(O4A)=1-FVAR(1)
 Sof(N2)=Sof(O4)=Sof(O3)=FVAR(1)
 Fixed Sof: O1W(0.25) H1WA(0.25) H1WB(0.25)
5.a Free rotating group:
 O1W(H1WA,H1WB)
5.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C9(H9A,H9B), C6(H6A,H6B), C8(H8A,H8B), C12(H12A,H12B), C7(H7A,
 H7B), C11(H11A,H11B), C3(H3A,H3B)
5.c Aromatic/amide H refined with riding coordinates:
 N5(H5), N3(H3)
;
_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
Cl1 Cl 0.84317(8) 0.27653(11) 0.49860(4) 0.0434(3) Uani 1 1 d . . . . .
O6 O -0.07883(16) 0.1944(3) 0.29456(11) 0.0414(6) Uani 1 1 d . . . . .
N8 N 0.79844(17) 0.5585(3) 0.40762(11) 0.0218(5) Uani 1 1 d . . . . .
N7 N 0.09449(19) 0.2120(4) 0.36393(13) 0.0340(6) Uani 1 1 d . . . . .
N9 N 0.79061(18) 0.9160(3) 0.39306(12) 0.0284(6) Uani 1 1 d . . . . .
N6 N -0.01045(19) 0.1972(4) 0.25850(13) 0.0337(6) Uani 1 1 d . . . . .
O5 O -0.02789(18) 0.1882(4) 0.19454(11) 0.0625(8) Uani 1 1 d . . . . .
O8 O 0.0884(2) 0.3646(4) 0.39121(12) 0.0637(8) Uani 1 1 d . . . . .
O7 O 0.1099(2) 0.0652(4) 0.39498(12) 0.0619(8) Uani 1 1 d . . . . .
N5 N 0.1629(2) 0.1998(4) 0.19067(13) 0.0460(8) Uani 1 1 d . . . . .
H5 H 0.104778 0.186792 0.166094 0.055 Uiso 1 1 calc R . . . .
N3 N 0.3340(2) 0.2016(5) 0.20429(15) 0.0508(9) Uani 1 1 d . . . . .
H3 H 0.390317 0.188960 0.188731 0.061 Uiso 1 1 calc R . . . .
N4 N 0.2528(2) 0.2187(5) 0.29983(13) 0.0454(8) Uani 1 1 d . . . . .
C0AA C 0.1684(2) 0.2073(4) 0.25738(14) 0.0273(7) Uani 1 1 d . . . . .
C5 C 0.0831(2) 0.2053(4) 0.28933(14) 0.0277(7) Uani 1 1 d . . . . .
N1 N 0.5160(2) 0.2064(4) 0.2994(2) 0.0531(9) Uani 1 1 d . . . . .
O2 O 0.58743(19) 0.2102(4) 0.34567(18) 0.0728(9) Uani 1 1 d . . . . .
O1 O 0.5260(2) 0.1972(5) 0.23711(18) 0.0833(11) Uani 1 1 d . . . . .
C2 C 0.3353(2) 0.2096(4) 0.27075(17) 0.0328(7) Uani 1 1 d . . . . .
C10 C 0.8976(2) 0.6450(4) 0.43001(16) 0.0297(7) Uani 1 1 d . . . . .
H10A H 0.945722 0.593665 0.402120 0.036 Uiso 1 1 calc R . . . .
H10B H 0.920151 0.614261 0.478731 0.036 Uiso 1 1 calc R . . . .
C9 C 0.7674(2) 0.6081(4) 0.33281(14) 0.0297(7) Uani 1 1 d . . . . .
H9A H 0.701982 0.554376 0.316466 0.036 Uiso 1 1 calc R . . . .
H9B H 0.814760 0.555829 0.304484 0.036 Uiso 1 1 calc R . . . .
C6 C 0.7642(2) 0.8241(4) 0.32668(15) 0.0339(8) Uani 1 1 d . . . . .
H6A H 0.809934 0.865287 0.295219 0.041 Uiso 1 1 calc R . . . .
H6B H 0.697317 0.863726 0.306651 0.041 Uiso 1 1 calc R . . . .
C8 C 0.7221(3) 0.8552(4) 0.43899(16) 0.0353(8) Uani 1 1 d . . . . .
H8A H 0.654951 0.894804 0.419754 0.042 Uiso 1 1 calc R . . . .
H8B H 0.739357 0.917185 0.484118 0.042 Uiso 1 1 calc R . . . .
N2 N 0.417(2) 0.244(4) 0.3876(15) 0.058(5) Uani 0.45(7) 1 d . U P A 1
C12 C 0.8030(3) 0.3485(4) 0.41326(15) 0.0326(8) Uani 1 1 d . . . . .
H12A H 0.848421 0.299010 0.382947 0.039 Uiso 1 1 calc R . . . .
H12B H 0.737206 0.295071 0.397736 0.039 Uiso 1 1 calc R . . . .
C7 C 0.8897(2) 0.8579(4) 0.42083(16) 0.0349(8) Uani 1 1 d . . . . .
H7A H 0.909272 0.919961 0.465706 0.042 Uiso 1 1 calc R . . . .
H7B H 0.935579 0.899560 0.389482 0.042 Uiso 1 1 calc R . . . .
C1 C 0.4234(2) 0.2106(5) 0.31619(19) 0.0414(9) Uani 1 1 d . . . . .
C11 C 0.7244(2) 0.6413(4) 0.44870(16) 0.0342(8) Uani 1 1 d . . . . .
H11A H 0.742641 0.610231 0.497861 0.041 Uiso 1 1 calc R . . . .
H11B H 0.658723 0.587663 0.432942 0.041 Uiso 1 1 calc R . . . .
C3 C 0.2472(3) 0.2119(5) 0.15531(17) 0.0399(8) Uani 1 1 d . . . . .
H3A H 0.246180 0.107133 0.122030 0.048 Uiso 1 1 calc R . . . .
H3B H 0.245903 0.332216 0.129778 0.048 Uiso 1 1 calc R . . . .
O4 O 0.425(2) 0.403(4) 0.4135(15) 0.094(5) Uani 0.45(7) 1 d . U P A 1
O3 O 0.400(2) 0.106(6) 0.4217(12) 0.087(6) Uani 0.45(7) 1 d . U P A 1
O3A O 0.427(2) 0.041(4) 0.4161(10) 0.089(5) Uani 0.55(7) 1 d . U P A 2
N2A N 0.4206(18) 0.196(4) 0.3913(10) 0.050(4) Uani 0.55(7) 1 d . U P A 2
O4A O 0.410(2) 0.344(5) 0.4189(11) 0.089(6) Uani 0.55(7) 1 d . U P A 2
O1W O 0.436(2) -0.281(3) 0.4570(9) 0.145(8) Uani 0.25 1 d . . P . .
H1WA H 0.467184 -0.174541 0.461919 0.217 Uiso 0.25 1 d G . P . .
H1WB H 0.397636 -0.279408 0.488588 0.217 Uiso 0.25 1 d G . P . .


_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
Cl1 C12 1.768(3) . ?
O6 N6 1.259(3) . ?
N8 C10 1.506(4) . ?
N8 C9 1.516(3) . ?
N8 C12 1.495(4) . ?
N8 C11 1.510(4) . ?
N7 O8 1.217(4) . ?
N7 O7 1.212(3) . ?
N7 C5 1.456(4) . ?
N9 C6 1.460(4) . ?
N9 C8 1.464(4) . ?
N9 C7 1.457(4) . ?
N6 O5 1.250(3) . ?
N6 C5 1.346(4) . ?
N5 H5 0.8800 . ?
N5 C0AA 1.307(4) . ?
N5 C3 1.441(4) . ?
N3 H3 0.8800 . ?
N3 C2 1.308(4) . ?
N3 C3 1.427(5) . ?
N4 C0AA 1.334(4) . ?
N4 C2 1.347(4) . ?
C0AA C5 1.412(4) . ?
N1 O2 1.243(4) . ?
N1 O1 1.255(4) . ?
N1 C1 1.365(4) . ?
C2 C1 1.402(5) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C7 1.524(4) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C6 1.538(4) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C11 1.530(5) . ?
N2 C1 1.44(3) . ?
N2 O4 1.23(2) . ?
N2 O3 1.23(2) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C1 N2A 1.49(2) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
O3A N2A 1.200(17) . ?
N2A O4A 1.205(17) . ?
O1W H1WA 0.8703 . ?
O1W H1WB 0.8699 . ?

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
C10 N8 C9 107.9(2) . . ?
C10 N8 C11 109.9(2) . . ?
C12 N8 C10 111.0(2) . . ?
C12 N8 C9 107.9(2) . . ?
C12 N8 C11 111.9(2) . . ?
C11 N8 C9 108.2(2) . . ?
O8 N7 C5 118.1(3) . . ?
O7 N7 O8 124.1(3) . . ?
O7 N7 C5 117.8(3) . . ?
C6 N9 C8 108.8(2) . . ?
C7 N9 C6 108.1(2) . . ?
C7 N9 C8 109.8(2) . . ?
O6 N6 C5 119.5(2) . . ?
O5 N6 O6 121.1(3) . . ?
O5 N6 C5 119.4(3) . . ?
C0AA N5 H5 118.3 . . ?
C0AA N5 C3 123.3(3) . . ?
C3 N5 H5 118.3 . . ?
C2 N3 H3 117.8 . . ?
C2 N3 C3 124.4(3) . . ?
C3 N3 H3 117.8 . . ?
C0AA N4 C2 116.4(3) . . ?
N5 C0AA N4 123.5(3) . . ?
N5 C0AA C5 121.1(3) . . ?
N4 C0AA C5 115.4(3) . . ?
N6 C5 N7 114.5(3) . . ?
N6 C5 C0AA 127.3(3) . . ?
C0AA C5 N7 118.2(3) . . ?
O2 N1 O1 122.2(3) . . ?
O2 N1 C1 119.4(4) . . ?
O1 N1 C1 118.4(3) . . ?
N3 C2 N4 122.4(3) . . ?
N3 C2 C1 121.7(3) . . ?
N4 C2 C1 115.8(3) . . ?
N8 C10 H10A 109.9 . . ?
N8 C10 H10B 109.9 . . ?
N8 C10 C7 108.9(2) . . ?
H10A C10 H10B 108.3 . . ?
C7 C10 H10A 109.9 . . ?
C7 C10 H10B 109.9 . . ?
N8 C9 H9A 110.1 . . ?
N8 C9 H9B 110.1 . . ?
N8 C9 C6 108.0(2) . . ?
H9A C9 H9B 108.4 . . ?
C6 C9 H9A 110.1 . . ?
C6 C9 H9B 110.1 . . ?
N9 C6 C9 112.0(2) . . ?
N9 C6 H6A 109.2 . . ?
N9 C6 H6B 109.2 . . ?
C9 C6 H6A 109.2 . . ?
C9 C6 H6B 109.2 . . ?
H6A C6 H6B 107.9 . . ?
N9 C8 H8A 109.3 . . ?
N9 C8 H8B 109.3 . . ?
N9 C8 C11 111.5(2) . . ?
H8A C8 H8B 108.0 . . ?
C11 C8 H8A 109.3 . . ?
C11 C8 H8B 109.3 . . ?
O4 N2 C1 123(2) . . ?
O3 N2 C1 116(2) . . ?
O3 N2 O4 121(3) . . ?
Cl1 C12 H12A 109.4 . . ?
Cl1 C12 H12B 109.4 . . ?
N8 C12 Cl1 111.25(19) . . ?
N8 C12 H12A 109.4 . . ?
N8 C12 H12B 109.4 . . ?
H12A C12 H12B 108.0 . . ?
N9 C7 C10 111.8(2) . . ?
N9 C7 H7A 109.3 . . ?
N9 C7 H7B 109.3 . . ?
C10 C7 H7A 109.3 . . ?
C10 C7 H7B 109.3 . . ?
H7A C7 H7B 107.9 . . ?
N1 C1 C2 126.9(3) . . ?
N1 C1 N2 115.8(13) . . ?
N1 C1 N2A 113.4(10) . . ?
C2 C1 N2 116.8(12) . . ?
C2 C1 N2A 119.4(10) . . ?
N8 C11 C8 108.8(2) . . ?
N8 C11 H11A 109.9 . . ?
N8 C11 H11B 109.9 . . ?
C8 C11 H11A 109.9 . . ?
C8 C11 H11B 109.9 . . ?
H11A C11 H11B 108.3 . . ?
N5 C3 H3A 109.9 . . ?
N5 C3 H3B 109.9 . . ?
N3 C3 N5 109.0(3) . . ?
N3 C3 H3A 109.9 . . ?
N3 C3 H3B 109.9 . . ?
H3A C3 H3B 108.3 . . ?
O3A N2A C1 117.4(14) . . ?
O3A N2A O4A 128.3(18) . . ?
O4A N2A C1 114.2(16) . . ?
H1WA O1W H1WB 104.5 . . ?

_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
_database_code_depnum_ccdc_archive 'CCDC 1892967'
loop_
_audit_author_name
_audit_author_address
'Chao Yan'
;School of Chemical Engineering, Nanjing University of Science and Technology
China
;
_audit_update_record             
;
2019-05-15 deposited with the CCDC.	2019-06-06 downloaded from the CCDC.
;
_vrf_RINTA01_1                   
;
PROBLEM: The value of Rint is greater than 0.18
RESPONSE: The diffraction of the crystal was very weak.
;

# end Validation Reply Form

_audit_creation_date             2018-08-27
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2016.07.08 svn.r3312 for OlexSys, GUI svn.r5203)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C9 H14 N10 O8'
_chemical_formula_sum            'C9 H14 N10 O8'
_chemical_formula_weight         390.30
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           56
_space_group_name_H-M_alt        'P c c n'
_space_group_name_Hall           '-P 2ab 2ac'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y+1/2, z'
'-x, y+1/2, -z+1/2'
'x+1/2, -y, -z+1/2'
'-x, -y, -z'
'x-1/2, y-1/2, -z'
'x, -y-1/2, z-1/2'
'-x-1/2, y, z-1/2'

_cell_length_a                   16.894(4)
_cell_length_b                   9.096(2)
_cell_length_c                   9.676(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1486.9(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    462
_cell_measurement_temperature    173
_cell_measurement_theta_max      22.12
_cell_measurement_theta_min      3.86
_shelx_estimated_absorpt_T_max   0.994
_shelx_estimated_absorpt_T_min   0.974
_exptl_absorpt_coefficient_mu    0.153
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear whiteish colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.744
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             808
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.04
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1923
_diffrn_reflns_av_unetI/netI     0.1363
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            5877
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.114
_diffrn_reflns_theta_max         25.114
_diffrn_reflns_theta_min         2.411
_diffrn_ambient_temperature      173
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                559
_reflns_number_total             1329
_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       'Bruker APEX 3'
_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         0.217
_refine_diff_density_min         -0.205
_refine_diff_density_rms         0.051
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     133
_refine_ls_number_reflns         1329
_refine_ls_number_restraints     120
_refine_ls_R_factor_all          0.1738
_refine_ls_R_factor_gt           0.0618
_refine_ls_restrained_S_all      1.005
_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)+(0.0070P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0612
_refine_ls_wR_factor_ref         0.0735
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups, All N(H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(O2) \\sim Ueq, Uanis(O2A) \\sim Ueq: with sigma of 0.005 and sigma for
terminal atoms of 0.01
3. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4. Others
 Sof(O2A)=1-FVAR(1)
 Sof(O2)=FVAR(1)
 Fixed Sof: H1A(0.5) H1B(0.5)
5.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C2(H2A,H2B), C4(H4A,H4B)
5.b Aromatic/amide H refined with riding coordinates:
 N3(H3), N2(H2)
;
_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
O4 O 0.34161(17) 0.2476(3) 0.4202(3) 0.0506(8) Uani 1 1 d . U . . .
N3 N 0.29780(19) 0.4307(3) 0.2350(3) 0.0382(10) Uani 1 1 d . U . . .
H3 H 0.2830 0.3749 0.3046 0.046 Uiso 1 1 calc R . . . .
N5 N 0.4113(2) 0.2961(3) 0.4179(4) 0.0427(10) Uani 1 1 d . U . . .
O1 O 0.53443(18) 0.5270(3) 0.2206(3) 0.0716(12) Uani 1 1 d . U . . .
N1 N 0.25806(19) 0.6213(3) 0.0768(3) 0.0399(9) Uani 1 1 d . U . . .
N2 N 0.39390(18) 0.5550(3) 0.1233(4) 0.0394(9) Uani 1 1 d . U . . .
H2 H 0.4432 0.5858 0.1188 0.047 Uiso 1 1 calc R . . . .
N4 N 0.5124(2) 0.4366(4) 0.3054(5) 0.0528(12) Uani 1 1 d . U . . .
O3 O 0.4604(2) 0.2500(4) 0.5007(3) 0.0787(12) Uani 1 1 d . U . . .
C3 C 0.3742(2) 0.4625(4) 0.2211(5) 0.0334(11) Uani 1 1 d . U . . .
C5 C 0.4313(2) 0.4003(4) 0.3170(4) 0.0350(11) Uani 1 1 d . U . . .
C1 C 0.2500 0.7500 0.1680(6) 0.0448(16) Uani 1 2 d S TU P . .
H1A H 0.2027 0.7398 0.2276 0.054 Uiso 0.5 1 calc R . . . .
H1B H 0.2973 0.7602 0.2276 0.054 Uiso 0.5 1 calc R . . . .
C2 C 0.3368(2) 0.6094(4) 0.0206(4) 0.0422(11) Uani 1 1 d . U . . .
H2A H 0.3541 0.7070 -0.0129 0.051 Uiso 1 1 calc R . . . .
H2B H 0.3359 0.5416 -0.0595 0.051 Uiso 1 1 calc R . . . .
C4 C 0.2374(2) 0.4848(4) 0.1392(4) 0.0431(12) Uani 1 1 d . U . . .
H4A H 0.2290 0.4106 0.0658 0.052 Uiso 1 1 calc R . . . .
H4B H 0.1869 0.4968 0.1898 0.052 Uiso 1 1 calc R . . . .
O2 O 0.5580(5) 0.4087(13) 0.4157(15) 0.067(3) Uani 0.58(2) 1 d . U . A 1
O2A O 0.5629(5) 0.3511(15) 0.332(2) 0.065(5) Uani 0.42(2) 1 d . U . A 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O4 N5 1.257(4) . ?
N3 H3 0.8800 . ?
N3 C3 1.329(4) . ?
N3 C4 1.464(4) . ?
N5 O3 1.227(4) . ?
N5 C5 1.402(5) . ?
O1 N4 1.220(4) . ?
N1 C1 1.472(4) . ?
N1 C2 1.441(4) . ?
N1 C4 1.424(4) . ?
N2 H2 0.8800 . ?
N2 C3 1.309(4) . ?
N2 C2 1.471(4) . ?
N4 C5 1.415(4) . ?
N4 O2 1.340(9) . ?
N4 O2A 1.182(8) . ?
C3 C5 1.454(5) . ?
C1 N1 1.472(4) 2_565 ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?

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
C3 N3 H3 118.7 . . ?
C3 N3 C4 122.6(4) . . ?
C4 N3 H3 118.7 . . ?
O4 N5 C5 118.3(4) . . ?
O3 N5 O4 120.1(4) . . ?
O3 N5 C5 121.5(4) . . ?
C2 N1 C1 111.8(3) . . ?
C4 N1 C1 114.6(3) . . ?
C4 N1 C2 108.7(3) . . ?
C3 N2 H2 118.8 . . ?
C3 N2 C2 122.5(3) . . ?
C2 N2 H2 118.8 . . ?
O1 N4 C5 120.4(4) . . ?
O1 N4 O2 119.2(5) . . ?
O2 N4 C5 116.7(5) . . ?
O2A N4 O1 111.6(7) . . ?
O2A N4 C5 121.9(6) . . ?
N3 C3 C5 119.6(4) . . ?
N2 C3 N3 117.4(4) . . ?
N2 C3 C5 122.9(4) . . ?
N5 C5 N4 116.5(4) . . ?
N5 C5 C3 123.3(4) . . ?
N4 C5 C3 120.1(4) . . ?
N1 C1 N1 106.4(5) 2_565 . ?
N1 C1 H1A 110.5 2_565 . ?
N1 C1 H1A 110.5 . . ?
N1 C1 H1B 110.5 2_565 . ?
N1 C1 H1B 110.5 . . ?
H1A C1 H1B 108.6 . . ?
N1 C2 N2 112.1(3) . . ?
N1 C2 H2A 109.2 . . ?
N1 C2 H2B 109.2 . . ?
N2 C2 H2A 109.2 . . ?
N2 C2 H2B 109.2 . . ?
H2A C2 H2B 107.9 . . ?
N3 C4 H4A 109.0 . . ?
N3 C4 H4B 109.0 . . ?
N1 C4 N3 113.0(3) . . ?
N1 C4 H4A 109.0 . . ?
N1 C4 H4B 109.0 . . ?
H4A C4 H4B 107.8 . . ?

_shelx_SHELXL_version_number     2014/7
_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_pl
_database_code_depnum_ccdc_archive 'CCDC 1892968'
loop_
_audit_author_name
_audit_author_address
'Chao Yan'
;School of Chemical Engineering, Nanjing University of Science and Technology
China
;
_audit_update_record             
;
2019-05-15 deposited with the CCDC.	2019-06-06 downloaded from the CCDC.
;
_audit_creation_date             2018-06-23
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2016.07.08 svn.r3312 for OlexSys, GUI svn.r5203)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C6 H8 N8 O10'
_chemical_formula_sum            'C6 H8 N8 O10'
_chemical_formula_weight         352.20
_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                   13.475(6)
_cell_length_b                   8.538(4)
_cell_length_c                   13.241(6)
_cell_angle_alpha                90
_cell_angle_beta                 115.838(11)
_cell_angle_gamma                90
_cell_volume                     1371.1(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    568
_cell_measurement_temperature    173
_cell_measurement_theta_max      18.36
_cell_measurement_theta_min      2.91
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.162
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.6037
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0815 before and 0.0618 after correction.
The Ratio of minimum to maximum transmission is 0.8098.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear whiteish colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.706
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.18
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1203
_diffrn_reflns_av_unetI/netI     0.1189
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            12162
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.599
_diffrn_reflns_theta_min         1.679
_diffrn_ambient_temperature      173
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1275
_reflns_number_total             3142
_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       'Bruker APEX 3'
_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    'SIR2004 (Burla et al., 2007)'
_refine_diff_density_max         0.259
_refine_diff_density_min         -0.241
_refine_diff_density_rms         0.059
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         3142
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1813
_refine_ls_R_factor_gt           0.0676
_refine_ls_restrained_S_all      1.001
_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)+(0.0642P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1449
_refine_ls_wR_factor_ref         0.1879
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups, All N(H) groups
2.a Riding coordinates:
 N3(H3), N4(H4)
2.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C4(H4A,H4B), C5(H5A,H5B)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.5029(3) 0.6384(3) 0.3385(2) 0.0670(9) Uani 1 1 d . . . . .
O2 O 0.3681(3) 0.7964(4) 0.3013(3) 0.0857(12) Uani 1 1 d . . . . .
O3 O 0.6296(3) 0.7461(6) 0.2561(3) 0.1258(18) Uani 1 1 d . . . . .
O4 O 0.5446(2) 0.7613(4) 0.0794(2) 0.0674(9) Uani 1 1 d . . . . .
O5 O -0.0195(3) 1.3237(7) -0.2046(4) 0.156(2) Uani 1 1 d . . . . .
O6 O 0.0353(3) 1.2682(4) -0.0303(3) 0.0863(12) Uani 1 1 d . . . . .
O7 O 0.1373(5) 1.5674(5) -0.0282(6) 0.170(2) Uani 1 1 d . . . . .
O8 O 0.3057(4) 1.4929(4) 0.0182(5) 0.140(2) Uani 1 1 d . . . . .
O9 O 0.1573(4) 1.2399(6) -0.2608(3) 0.1165(16) Uani 1 1 d . . . . .
O10 O 0.1753(4) 1.4874(5) -0.2297(4) 0.150(2) Uani 1 1 d . . . . .
N1 N 0.5419(3) 0.7588(4) 0.1707(3) 0.0562(10) Uani 1 1 d . . . . .
N2 N 0.4392(3) 0.7385(4) 0.2773(3) 0.0472(9) Uani 1 1 d . . . . .
N3 N 0.3450(2) 0.8714(3) -0.0145(2) 0.0344(7) Uani 1 1 d . . . . .
H3 H 0.4026 0.8422 -0.0247 0.041 Uiso 1 1 d R . . . .
N4 N 0.2592(3) 0.8923(3) 0.0993(2) 0.0407(8) Uani 1 1 d . . . . .
H4 H 0.2608 0.8855 0.1662 0.049 Uiso 1 1 d R . . . .
N5 N 0.1873(2) 1.0406(3) -0.0706(2) 0.0331(7) Uani 1 1 d . . . . .
N6 N 0.2061(5) 1.4768(5) -0.0269(5) 0.1016(17) Uani 1 1 d . . . . .
N7 N 0.0493(3) 1.3068(5) -0.1094(4) 0.0767(13) Uani 1 1 d . . . . .
N8 N 0.1671(4) 1.3533(6) -0.2045(4) 0.0846(15) Uani 1 1 d . . . . .
C1 C 0.4423(3) 0.7846(4) 0.1770(3) 0.0355(9) Uani 1 1 d . . . . .
C2 C 0.3473(3) 0.8505(4) 0.0849(3) 0.0300(8) Uani 1 1 d . . . . .
C3 C 0.1605(3) 0.9515(4) 0.0060(3) 0.0453(10) Uani 1 1 d . . . . .
H3A H 0.1126 0.8625 -0.0344 0.054 Uiso 1 1 calc R . . . .
H3B H 0.1190 1.0184 0.0353 0.054 Uiso 1 1 calc R . . . .
C4 C 0.2519(3) 0.9427(4) -0.1093(3) 0.0444(10) Uani 1 1 d . . . . .
H4A H 0.2798 1.0068 -0.1537 0.053 Uiso 1 1 calc R . . . .
H4B H 0.2044 0.8592 -0.1586 0.053 Uiso 1 1 calc R . . . .
C5 C 0.2397(3) 1.1897(4) -0.0250(3) 0.0338(9) Uani 1 1 d . . . . .
H5A H 0.3116 1.1955 -0.0284 0.041 Uiso 1 1 calc R . . . .
H5B H 0.2537 1.1974 0.0547 0.041 Uiso 1 1 calc R . . . .
C6 C 0.1675(3) 1.3254(4) -0.0903(4) 0.0495(11) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 N2 1.232(4) . ?
O2 N2 1.237(4) . ?
O3 N1 1.234(4) . ?
O4 N1 1.225(4) . ?
O5 N7 1.204(5) . ?
O6 N7 1.189(5) . ?
O7 N6 1.202(5) . ?
O8 N6 1.215(5) . ?
O9 N8 1.193(6) . ?
O10 N8 1.211(5) . ?
N1 C1 1.397(5) . ?
N2 C1 1.403(4) . ?
N3 H3 0.8799 . ?
N3 C2 1.315(4) . ?
N3 C4 1.465(4) . ?
N4 H4 0.8785 . ?
N4 C2 1.330(4) . ?
N4 C3 1.456(5) . ?
N5 C3 1.434(4) . ?
N5 C4 1.452(4) . ?
N5 C5 1.454(4) . ?
N6 C6 1.506(6) . ?
N7 C6 1.507(5) . ?
N8 C6 1.529(6) . ?
C1 C2 1.444(5) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5 C6 1.518(5) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O3 N1 C1 121.3(3) . . ?
O4 N1 O3 118.5(4) . . ?
O4 N1 C1 119.9(3) . . ?
O1 N2 O2 120.2(3) . . ?
O1 N2 C1 121.2(3) . . ?
O2 N2 C1 118.5(3) . . ?
C2 N3 H3 118.5 . . ?
C2 N3 C4 123.4(3) . . ?
C4 N3 H3 118.0 . . ?
C2 N4 H4 119.7 . . ?
C2 N4 C3 120.9(3) . . ?
C3 N4 H4 119.4 . . ?
C3 N5 C4 108.5(3) . . ?
C3 N5 C5 113.4(3) . . ?
C4 N5 C5 113.2(3) . . ?
O7 N6 O8 127.9(5) . . ?
O7 N6 C6 117.9(5) . . ?
O8 N6 C6 114.2(4) . . ?
O5 N7 C6 116.0(5) . . ?
O6 N7 O5 127.5(5) . . ?
O6 N7 C6 116.3(4) . . ?
O9 N8 O10 126.4(6) . . ?
O9 N8 C6 116.3(4) . . ?
O10 N8 C6 117.3(6) . . ?
N1 C1 N2 116.0(3) . . ?
N1 C1 C2 122.1(3) . . ?
N2 C1 C2 121.9(3) . . ?
N3 C2 N4 118.3(3) . . ?
N3 C2 C1 121.6(3) . . ?
N4 C2 C1 120.1(3) . . ?
N4 C3 H3A 109.3 . . ?
N4 C3 H3B 109.3 . . ?
N5 C3 N4 111.5(3) . . ?
N5 C3 H3A 109.3 . . ?
N5 C3 H3B 109.3 . . ?
H3A C3 H3B 108.0 . . ?
N3 C4 H4A 109.4 . . ?
N3 C4 H4B 109.4 . . ?
N5 C4 N3 111.0(3) . . ?
N5 C4 H4A 109.4 . . ?
N5 C4 H4B 109.4 . . ?
H4A C4 H4B 108.0 . . ?
N5 C5 H5A 109.5 . . ?
N5 C5 H5B 109.5 . . ?
N5 C5 C6 110.9(3) . . ?
H5A C5 H5B 108.0 . . ?
C6 C5 H5A 109.5 . . ?
C6 C5 H5B 109.5 . . ?
N6 C6 N7 105.5(4) . . ?
N6 C6 N8 105.6(4) . . ?
N6 C6 C5 111.0(4) . . ?
N7 C6 N8 107.6(4) . . ?
N7 C6 C5 112.6(3) . . ?
C5 C6 N8 114.0(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 N2 C1 N1 -22.9(5) . . . . ?
O1 N2 C1 C2 155.3(3) . . . . ?
O2 N2 C1 N1 159.7(4) . . . . ?
O2 N2 C1 C2 -22.0(5) . . . . ?
O3 N1 C1 N2 -22.8(6) . . . . ?
O3 N1 C1 C2 158.9(4) . . . . ?
O4 N1 C1 N2 163.2(4) . . . . ?
O4 N1 C1 C2 -15.0(6) . . . . ?
O5 N7 C6 N6 109.2(6) . . . . ?
O5 N7 C6 N8 -3.2(6) . . . . ?
O5 N7 C6 C5 -129.7(5) . . . . ?
O6 N7 C6 N6 -75.1(5) . . . . ?
O6 N7 C6 N8 172.6(4) . . . . ?
O6 N7 C6 C5 46.1(6) . . . . ?
O7 N6 C6 N7 -17.7(7) . . . . ?
O7 N6 C6 N8 96.1(6) . . . . ?
O7 N6 C6 C5 -139.9(6) . . . . ?
O8 N6 C6 N7 163.7(5) . . . . ?
O8 N6 C6 N8 -82.5(6) . . . . ?
O8 N6 C6 C5 41.6(6) . . . . ?
O9 N8 C6 N6 167.5(5) . . . . ?
O9 N8 C6 N7 -80.1(6) . . . . ?
O9 N8 C6 C5 45.4(6) . . . . ?
O10 N8 C6 N6 -13.4(6) . . . . ?
O10 N8 C6 N7 98.9(5) . . . . ?
O10 N8 C6 C5 -135.5(5) . . . . ?
N1 C1 C2 N3 8.6(5) . . . . ?
N1 C1 C2 N4 -171.1(3) . . . . ?
N2 C1 C2 N3 -169.5(3) . . . . ?
N2 C1 C2 N4 10.7(5) . . . . ?
N5 C5 C6 N6 165.2(3) . . . . ?
N5 C5 C6 N7 47.2(5) . . . . ?
N5 C5 C6 N8 -75.7(4) . . . . ?
C2 N3 C4 N5 23.2(5) . . . . ?
C2 N4 C3 N5 -33.9(4) . . . . ?
C3 N4 C2 N3 3.4(5) . . . . ?
C3 N4 C2 C1 -176.9(3) . . . . ?
C3 N5 C4 N3 -51.2(4) . . . . ?
C3 N5 C5 C6 -115.5(3) . . . . ?
C4 N3 C2 N4 1.9(5) . . . . ?
C4 N3 C2 C1 -177.9(3) . . . . ?
C4 N5 C3 N4 56.7(4) . . . . ?
C4 N5 C5 C6 120.3(3) . . . . ?
C5 N5 C3 N4 -70.0(4) . . . . ?
C5 N5 C4 N3 75.6(4) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
