# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry A.
# 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_20180028-wy-01-08_0m
_database_code_depnum_ccdc_archive 'CCDC 1831628'
loop_
_audit_author_name
_audit_author_address
'Song Siwei'
;CAEP
China
;
_audit_update_record             
;
2018-03-22 deposited with the CCDC.	2019-07-15 downloaded from the CCDC.
;
_audit_creation_date             2018-03-22
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C4 H6 N6 O4, H O'
_chemical_formula_sum            'C4 H7 N6 O5'
_chemical_formula_weight         219.16
_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      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-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                   14.128(7)
_cell_length_b                   14.696(8)
_cell_length_c                   7.415(4)
_cell_angle_alpha                90
_cell_angle_beta                 98.866(14)
_cell_angle_gamma                90
_cell_volume                     1521.1(14)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    1114
_cell_measurement_temperature    100
_cell_measurement_theta_max      27.38
_cell_measurement_theta_min      2.75
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.174
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6575
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
'? was used for absorption correction. wR2(int) was 0.0642 before and 0.0492 after correction. The Ratio of minimum to maximum transmission is 0.8818. 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    1.914
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             904
_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  0.0339
_diffrn_reflns_av_unetI/netI     0.0436
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            4861
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.480
_diffrn_reflns_theta_min         2.012
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.981
_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                1279
_reflns_number_total             1714
_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-1997 (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2008)'
_refine_diff_density_max         0.511
_refine_diff_density_min         -0.330
_refine_diff_density_rms         0.095
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.121
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     157
_refine_ls_number_reflns         1714
_refine_ls_number_restraints     14
_refine_ls_R_factor_all          0.0718
_refine_ls_R_factor_gt           0.0535
_refine_ls_restrained_S_all      1.124
_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)+(0.1090P)²+0.9139P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1555
_refine_ls_wR_factor_ref         0.1903
_refine_special_details          ?
_olex2_refinement_description    
;
1. Others
 Fixed Sof: O5(0.55) O5A(0.45)
 Fixed Uiso: H1A(0.017) H1B(0.017) H2A(0.016) H2B(0.016)
 Fixed X: H1A(0.4083) H1B(0.4133) H2A(0.1895) H2B(0.1022)
 Fixed Y: H1A(0.7187) H1B(0.6152) H2A(0.4495) H2B(0.4884)
 Fixed Z: H1A(0.6207) H1B(0.6304) H2A(0.839) H2B(0.9098)
;
_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
O4 O 0.01733(12) 0.73581(11) 0.9775(2) 0.0196(4) Uani 1 1 d . . . . .
O1 O 0.31780(11) 0.50861(10) 0.7388(2) 0.0156(4) Uani 1 1 d . . . . .
O3 O 0.01911(12) 0.58906(11) 0.9830(2) 0.0191(4) Uani 1 1 d . . . . .
O2 O 0.29998(13) 0.82020(11) 0.6917(3) 0.0224(5) Uani 1 1 d . . . . .
N6 N 0.26679(13) 0.58447(11) 0.7618(2) 0.0114(4) Uani 1 1 d . . . . .
N3 N 0.05473(14) 0.66252(12) 0.9460(3) 0.0135(5) Uani 1 1 d . . . . .
N4 N 0.14431(15) 0.82962(13) 0.8358(3) 0.0157(5) Uani 1 1 d . . . . .
N1 N 0.38367(14) 0.66640(12) 0.6479(3) 0.0145(5) Uani 1 1 d . . . . .
H1A H 0.4083 0.7187 0.6207 0.017 Uiso 1 1 calc R . . . .
H1B H 0.4133 0.6152 0.6304 0.017 Uiso 1 1 calc R . . . .
N5 N 0.25888(13) 0.74357(12) 0.7399(3) 0.0130(5) Uani 1 1 d . . . . .
N2 N 0.15537(13) 0.49669(13) 0.8639(3) 0.0135(4) Uani 1 1 d . . . . .
H2A H 0.1895 0.4495 0.8390 0.016 Uiso 1 1 calc R . . . .
H2B H 0.1022 0.4884 0.9098 0.016 Uiso 1 1 calc R . . . .
C2 C 0.18372(15) 0.57897(15) 0.8328(3) 0.0112(5) Uani 1 1 d . . . . .
C1 C 0.30345(17) 0.66468(14) 0.7139(3) 0.0134(5) Uani 1 1 d . . . . .
C3 C 0.13816(16) 0.66279(14) 0.8635(3) 0.0124(5) Uani 1 1 d . . . . .
C4 C 0.17741(16) 0.74690(15) 0.8160(3) 0.0133(5) Uani 1 1 d . . . . .
H4A H 0.095(2) 0.8376(16) 0.886(4) 0.008(6) Uiso 1 1 d . . . . .
H4B H 0.175(2) 0.878(2) 0.798(4) 0.035(9) Uiso 1 1 d . . . . .
O5 O 0.5190(3) 0.5435(2) 0.5400(6) 0.0249(8) Uani 0.55 1 d D U P A 1
O5A O 0.4786(3) 0.5412(3) 0.4498(7) 0.0207(9) Uani 0.45 1 d D U P B 2
H5 H 0.5376(15) 0.5135(19) 0.451(3) 0.024(8) Uiso 1 1 d D . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O4 N3 1.238(2) . ?
O1 N6 1.352(2) . ?
O3 N3 1.240(2) . ?
O2 N5 1.341(2) . ?
N6 C2 1.361(3) . ?
N6 C1 1.357(3) . ?
N3 C3 1.409(3) . ?
N4 C4 1.319(3) . ?
N4 H4A 0.84(3) . ?
N4 H4B 0.90(4) . ?
N1 H1A 0.8800 . ?
N1 H1B 0.8800 . ?
N1 C1 1.302(3) . ?
N5 C1 1.347(3) . ?
N5 C4 1.359(3) . ?
N2 H2A 0.8800 . ?
N2 H2B 0.8800 . ?
N2 C2 1.305(3) . ?
C2 C3 1.424(3) . ?
C3 C4 1.421(3) . ?
O5 O5 1.476(7) 5_666 ?
O5 H5 0.865(17) . ?
O5A O5A 1.500(8) 5_666 ?
O5A H5 0.925(17) . ?

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 N6 C2 120.52(17) . . ?
O1 N6 C1 116.80(17) . . ?
C1 N6 C2 122.67(18) . . ?
O4 N3 O3 121.08(18) . . ?
O4 N3 C3 119.31(17) . . ?
O3 N3 C3 119.60(17) . . ?
C4 N4 H4A 120.5(16) . . ?
C4 N4 H4B 120(2) . . ?
H4A N4 H4B 120(3) . . ?
H1A N1 H1B 120.0 . . ?
C1 N1 H1A 120.0 . . ?
C1 N1 H1B 120.0 . . ?
O2 N5 C1 116.96(17) . . ?
O2 N5 C4 120.67(17) . . ?
C1 N5 C4 122.35(18) . . ?
H2A N2 H2B 120.0 . . ?
C2 N2 H2A 120.0 . . ?
C2 N2 H2B 120.0 . . ?
N6 C2 C3 116.64(19) . . ?
N2 C2 N6 115.45(19) . . ?
N2 C2 C3 127.9(2) . . ?
N1 C1 N6 120.31(19) . . ?
N1 C1 N5 119.36(19) . . ?
N5 C1 N6 120.29(19) . . ?
N3 C3 C2 119.72(18) . . ?
N3 C3 C4 119.62(18) . . ?
C4 C3 C2 120.6(2) . . ?
N4 C4 N5 114.65(19) . . ?
N4 C4 C3 128.0(2) . . ?
N5 C4 C3 117.34(19) . . ?
O5 O5 H5 52(2) 5_666 . ?
O5A O5A H5 49.1(19) 5_666 . ?

_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_wy
_database_code_depnum_ccdc_archive 'CCDC 1887847'
loop_
_audit_author_name
_audit_author_address
SV
;CAEP
China
;
_audit_update_record             
;
2018-12-29 deposited with the CCDC.	2019-07-15 downloaded from the CCDC.
;
_audit_creation_date             2018-05-31
_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         'Cl O4, C4 H7 N6 O4'
_chemical_formula_sum            'C4 H7 Cl N6 O8'
_chemical_formula_weight         302.61
_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      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                   12.410(2)
_cell_length_b                   9.9590(19)
_cell_length_c                   16.305(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2015.2(7)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    1192
_cell_measurement_temperature    173
_cell_measurement_theta_max      22.48
_cell_measurement_theta_min      2.99
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.439
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6009
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1312 before and 0.0718 after correction.
The Ratio of minimum to maximum transmission is 0.8061.
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    1.995
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1232
_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  0.0800
_diffrn_reflns_av_unetI/netI     0.0600
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            9864
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.810
_diffrn_reflns_theta_min         2.498
_diffrn_ambient_temperature      173
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_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                1569
_reflns_number_total             2146
_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         0.405
_refine_diff_density_min         -0.467
_refine_diff_density_rms         0.083
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     176
_refine_ls_number_reflns         2146
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0685
_refine_ls_R_factor_gt           0.0456
_refine_ls_restrained_S_all      1.046
_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)+(0.0407P)²+1.2268P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1001
_refine_ls_wR_factor_ref         0.1124
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All N(H,H) groups
2. Restrained distances
 O1-H1
 0.84 with sigma of 0.02
3.a X=CH2 refined with riding coordinates:
 N1(H1A,H1B), N3(H3A,H3B), N5(H5A,H5B)
;
_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 0.63526(5) 0.18419(7) 0.40307(4) 0.0195(2) Uani 1 1 d . . . . .
O2 O 0.61532(15) 0.51322(19) 0.55149(12) 0.0187(5) Uani 1 1 d . . . . .
O1 O 0.86154(15) 0.2016(2) 0.64791(13) 0.0191(5) Uani 1 1 d D . . . .
O4 O 0.50288(17) 0.0366(2) 0.74604(12) 0.0243(5) Uani 1 1 d . . . . .
O3 O 0.39056(16) 0.1554(2) 0.67571(13) 0.0255(5) Uani 1 1 d . . . . .
N6 N 0.75604(18) 0.2390(2) 0.64092(14) 0.0154(5) Uani 1 1 d . . . . .
N4 N 0.48357(19) 0.1279(2) 0.69726(14) 0.0181(5) Uani 1 1 d . . . . .
N1 N 0.81366(18) 0.4144(2) 0.55829(14) 0.0181(5) Uani 1 1 d . . . . .
H1A H 0.8001 0.4864 0.5310 0.022 Uiso 1 1 calc R . . . .
H1B H 0.8785 0.3843 0.5610 0.022 Uiso 1 1 calc R . . . .
O7 O 0.72006(18) 0.1618(2) 0.46195(14) 0.0366(6) Uani 1 1 d . . . . .
N2 N 0.63367(18) 0.3956(2) 0.59227(14) 0.0153(5) Uani 1 1 d . . . . .
N3 N 0.45229(18) 0.3693(2) 0.59753(15) 0.0202(6) Uani 1 1 d . . . . .
H3A H 0.4478 0.4434 0.5706 0.024 Uiso 1 1 calc R . . . .
H3B H 0.3947 0.3271 0.6114 0.024 Uiso 1 1 calc R . . . .
N5 N 0.7106(2) 0.0717(2) 0.72942(14) 0.0198(6) Uani 1 1 d . . . . .
H5A H 0.7784 0.0554 0.7340 0.024 Uiso 1 1 calc R . . . .
H5B H 0.6648 0.0243 0.7563 0.024 Uiso 1 1 calc R . . . .
O6 O 0.54650(17) 0.0981(3) 0.42496(15) 0.0387(6) Uani 1 1 d . . . . .
O5 O 0.6041(2) 0.3213(2) 0.40430(16) 0.0428(7) Uani 1 1 d . . . . .
O8 O 0.6754(2) 0.1490(2) 0.32411(14) 0.0427(7) Uani 1 1 d . . . . .
C1 C 0.7362(2) 0.3511(3) 0.59535(16) 0.0152(6) Uani 1 1 d . . . . .
C2 C 0.5462(2) 0.3211(3) 0.61718(16) 0.0152(6) Uani 1 1 d . . . . .
C4 C 0.6773(2) 0.1685(3) 0.68157(16) 0.0151(6) Uani 1 1 d . . . . .
C3 C 0.5699(2) 0.2044(3) 0.66387(16) 0.0147(6) Uani 1 1 d . . . . .
H1 H 0.870(3) 0.138(3) 0.6115(19) 0.050(12) 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
Cl1 O7 1.442(2) . ?
Cl1 O6 1.441(2) . ?
Cl1 O5 1.419(2) . ?
Cl1 O8 1.424(2) . ?
O2 N2 1.366(3) . ?
O1 N6 1.366(3) . ?
O1 H1 0.877(19) . ?
O4 N4 1.232(3) . ?
O3 N4 1.237(3) . ?
N6 C1 1.364(3) . ?
N6 C4 1.374(4) . ?
N4 C3 1.423(4) . ?
N1 H1A 0.8600 . ?
N1 H1B 0.8600 . ?
N1 C1 1.299(4) . ?
N2 C1 1.348(3) . ?
N2 C2 1.376(3) . ?
N3 H3A 0.8600 . ?
N3 H3B 0.8600 . ?
N3 C2 1.301(3) . ?
N5 H5A 0.8600 . ?
N5 H5B 0.8600 . ?
N5 C4 1.308(3) . ?
C2 C3 1.420(4) . ?
C4 C3 1.410(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O6 Cl1 O7 107.51(14) . . ?
O5 Cl1 O7 109.76(15) . . ?
O5 Cl1 O6 111.15(15) . . ?
O5 Cl1 O8 110.17(15) . . ?
O8 Cl1 O7 107.99(16) . . ?
O8 Cl1 O6 110.17(15) . . ?
N6 O1 H1 105(2) . . ?
O1 N6 C4 120.1(2) . . ?
C1 N6 O1 116.2(2) . . ?
C1 N6 C4 123.6(2) . . ?
O4 N4 O3 121.9(2) . . ?
O4 N4 C3 119.7(2) . . ?
O3 N4 C3 118.4(2) . . ?
H1A N1 H1B 120.0 . . ?
C1 N1 H1A 120.0 . . ?
C1 N1 H1B 120.0 . . ?
O2 N2 C2 118.4(2) . . ?
C1 N2 O2 117.2(2) . . ?
C1 N2 C2 123.8(2) . . ?
H3A N3 H3B 120.0 . . ?
C2 N3 H3A 120.0 . . ?
C2 N3 H3B 120.0 . . ?
H5A N5 H5B 120.0 . . ?
C4 N5 H5A 120.0 . . ?
C4 N5 H5B 120.0 . . ?
N1 C1 N6 121.1(3) . . ?
N1 C1 N2 121.5(3) . . ?
N2 C1 N6 117.4(2) . . ?
N2 C2 C3 115.9(2) . . ?
N3 C2 N2 115.8(3) . . ?
N3 C2 C3 128.3(3) . . ?
N6 C4 C3 116.3(2) . . ?
N5 C4 N6 116.1(3) . . ?
N5 C4 C3 127.5(3) . . ?
C2 C3 N4 119.2(2) . . ?
C4 C3 N4 119.9(2) . . ?
C4 C3 C2 120.9(2) . . ?

_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_20180195-wy-102-n_0m
_database_code_depnum_ccdc_archive 'CCDC 1887848'
loop_
_audit_author_name
_audit_author_address
sv
;CAEP
China
;
_audit_update_record             
;
2018-12-29 deposited with the CCDC.	2019-07-15 downloaded from the CCDC.
;
_audit_creation_date             2018-03-20
_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         'C4 H7 N6 O4, N O3'
_chemical_formula_sum            'C4 H7 N7 O7'
_chemical_formula_weight         265.17
_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                   11.239(3)
_cell_length_b                   11.869(3)
_cell_length_c                   13.511(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1802.2(7)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    1238
_cell_measurement_temperature    173
_cell_measurement_theta_max      22.06
_cell_measurement_theta_min      2.92
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.184
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6178
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0869 before and 0.0660 after correction.
The Ratio of minimum to maximum transmission is 0.8286.
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    1.955
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1088
_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  0.0801
_diffrn_reflns_av_unetI/netI     0.0507
_diffrn_reflns_Laue_measured_fraction_full 0.980
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            12301
_diffrn_reflns_point_group_measured_fraction_full 0.980
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        25.123
_diffrn_reflns_theta_max         25.123
_diffrn_reflns_theta_min         3.015
_diffrn_ambient_temperature      173
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.980
_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                1206
_reflns_number_total             1577
_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         0.492
_refine_diff_density_min         -0.295
_refine_diff_density_rms         0.070
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         1577
_refine_ls_number_restraints     21
_refine_ls_R_factor_all          0.0625
_refine_ls_R_factor_gt           0.0447
_refine_ls_restrained_S_all      1.080
_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)+(0.0755P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1137
_refine_ls_wR_factor_ref         0.1268
_refine_special_details          ?
_olex2_refinement_description    
;
1. Restrained distances
 C4-N4
 1.305 with sigma of 0.02
 N6-H6A
 0.78 with sigma of 0.02
 H4B-N4 = H4A-N4
 0.78 with sigma of 0.02
 C4-H4B = C4-H4A
 1.9 with sigma of 0.02
 H4B-H4A
 1.52 with sigma of 0.02
 O4-H4
 0.78 with sigma of 0.02
2. Rigid bond restraints
 C4, N4
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.001
3. Uiso/Uaniso restraints and constraints
C4 \\sim N4: within 2A with sigma of 0.02 and sigma for terminal atoms of 0.01
Uanis(N4) \\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.01
;
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O3 O 0.54979(15) 0.17475(15) 0.66898(14) 0.0253(5) Uani 1 1 d . . . . .
O5 O 0.09523(14) 0.33601(16) 0.55645(14) 0.0262(5) Uani 1 1 d . . . . .
O4 O 0.23536(15) 0.43371(17) 0.68341(15) 0.0268(5) Uani 1 1 d D . . . .
N4 N 0.32321(17) 0.22481(17) 0.70234(16) 0.0157(5) Uani 1 1 d D U . . .
O6 O -0.03781(16) 0.41835(17) 0.64760(15) 0.0302(5) Uani 1 1 d . . . . .
O1 O 0.58360(16) 0.65920(16) 0.58224(15) 0.0324(5) Uani 1 1 d . . . . .
O2 O 0.73103(15) 0.54491(17) 0.59188(17) 0.0365(6) Uani 1 1 d . . . . .
N7 N -0.00552(17) 0.38336(17) 0.56640(17) 0.0199(5) Uani 1 1 d . . . . .
N5 N 0.35156(16) 0.40780(19) 0.65792(16) 0.0199(5) Uani 1 1 d . . . . .
N3 N 0.50746(17) 0.28233(17) 0.65428(17) 0.0204(5) Uani 1 1 d . . . . .
N1 N 0.62342(17) 0.56360(18) 0.59765(16) 0.0211(5) Uani 1 1 d . . . . .
N6 N 0.3694(2) 0.5951(2) 0.62729(18) 0.0241(6) Uani 1 1 d D . . . .
N2 N 0.69682(18) 0.3277(2) 0.60976(18) 0.0238(5) Uani 1 1 d . . . . .
C1 C 0.4220(2) 0.4975(2) 0.63510(17) 0.0175(6) Uani 1 1 d . . . . .
C3 C 0.5886(2) 0.3627(2) 0.62762(19) 0.0197(6) Uani 1 1 d . . . . .
C2 C 0.5450(2) 0.4746(2) 0.62050(18) 0.0179(6) Uani 1 1 d . . . . .
C4 C 0.3891(2) 0.2998(2) 0.67525(19) 0.0209(6) Uani 1 1 d D U . . .
O7 O -0.07111(15) 0.39183(16) 0.49191(14) 0.0260(5) Uani 1 1 d . . . . .
H2A H 0.713(3) 0.255(3) 0.614(2) 0.034(9) Uiso 1 1 d . . . . .
H6A H 0.3008(18) 0.603(3) 0.647(2) 0.037(9) Uiso 1 1 d D . . . .
H6B H 0.415(3) 0.655(3) 0.612(2) 0.036(8) Uiso 1 1 d . . . . .
H2B H 0.748(3) 0.382(3) 0.590(3) 0.047(10) Uiso 1 1 d . . . . .
H4 H 0.196(3) 0.395(3) 0.643(3) 0.067(14) Uiso 1 1 d D . . . .
H4A H 0.2474(17) 0.235(3) 0.709(5) 0.17(3) Uiso 1 1 d D . . . .
H4B H 0.346(3) 0.1558(15) 0.704(5) 0.14(2) Uiso 1 1 d D . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O3 N3 1.377(3) . ?
O5 N7 1.271(3) . ?
O4 N5 1.385(3) . ?
O4 H4 0.840(19) . ?
N4 C4 1.214(3) . ?
N4 H4A 0.865(17) . ?
N4 H4B 0.860(16) . ?
O6 N7 1.228(3) . ?
O1 N1 1.237(3) . ?
O2 N1 1.232(3) . ?
N7 O7 1.252(3) . ?
N5 C1 1.362(3) . ?
N5 C4 1.370(4) . ?
N3 C3 1.368(3) . ?
N3 C4 1.376(3) . ?
N1 C2 1.410(3) . ?
N6 C1 1.305(3) . ?
N6 H6A 0.821(18) . ?
N6 H6B 0.91(3) . ?
N2 C3 1.308(3) . ?
N2 H2A 0.88(3) . ?
N2 H2B 0.91(4) . ?
C1 C2 1.422(3) . ?
C3 C2 1.420(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N5 O4 H4 102(3) . . ?
C4 N4 H4A 122(2) . . ?
C4 N4 H4B 121(2) . . ?
H4A N4 H4B 115(2) . . ?
O6 N7 O5 120.5(2) . . ?
O6 N7 O7 121.1(2) . . ?
O7 N7 O5 118.4(2) . . ?
C1 N5 O4 115.5(2) . . ?
C1 N5 C4 126.3(2) . . ?
C4 N5 O4 117.1(2) . . ?
C3 N3 O3 117.01(19) . . ?
C3 N3 C4 126.4(2) . . ?
C4 N3 O3 116.3(2) . . ?
O1 N1 C2 119.8(2) . . ?
O2 N1 O1 120.6(2) . . ?
O2 N1 C2 119.5(2) . . ?
C1 N6 H6A 120(2) . . ?
C1 N6 H6B 117(2) . . ?
H6A N6 H6B 122(3) . . ?
C3 N2 H2A 119(2) . . ?
C3 N2 H2B 115(2) . . ?
H2A N2 H2B 126(3) . . ?
N5 C1 C2 116.5(2) . . ?
N6 C1 N5 116.7(2) . . ?
N6 C1 C2 126.8(2) . . ?
N3 C3 C2 116.1(2) . . ?
N2 C3 N3 116.6(2) . . ?
N2 C3 C2 127.3(2) . . ?
N1 C2 C1 119.7(2) . . ?
N1 C2 C3 120.0(2) . . ?
C3 C2 C1 120.4(2) . . ?
N4 C4 N5 123.4(2) . . ?
N4 C4 N3 122.8(2) . . ?
N5 C4 N3 113.8(2) . . ?

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