# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_22020930_0m
_database_code_depnum_ccdc_archive 'CCDC 2078514'
loop_
_audit_author_name
_audit_author_address
'Caijin Lei'
;Nanjing University of Science and Technology
China
;
_audit_update_record             
;
2021-04-19 deposited with the CCDC.	2021-09-08 downloaded from the CCDC.
;
_audit_creation_date             2020-11-23
_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         'C5 H7 N10 O, H2 O, N O3'
_chemical_formula_sum            'C5 H9 N11 O5'
_chemical_formula_weight         303.23
_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'
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                   7.0384(3)
_cell_length_b                   13.0429(6)
_cell_length_c                   12.7579(6)
_cell_angle_alpha                90
_cell_angle_beta                 104.682(2)
_cell_angle_gamma                90
_cell_volume                     1132.95(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5647
_cell_measurement_temperature    160
_cell_measurement_theta_max      27.488
_cell_measurement_theta_min      2.272
_shelx_estimated_absorpt_T_max   0.991
_shelx_estimated_absorpt_T_min   0.974
_exptl_absorpt_coefficient_mu    0.156
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6856
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1233 before and 0.0536 after correction. The Ratio of minimum to maximum transmission is 0.9195. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.778
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.06
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0401
_diffrn_reflns_av_unetI/netI     0.0321
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            12695
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.539
_diffrn_reflns_theta_min         2.272
_diffrn_ambient_temperature      160.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2105
_reflns_number_total             2580
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_refine_diff_density_max         0.355
_refine_diff_density_min         -0.273
_refine_diff_density_rms         0.052
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         2580
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0549
_refine_ls_R_factor_gt           0.0411
_refine_ls_restrained_S_all      1.019
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0538P)²+0.6314P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1000
_refine_ls_wR_factor_ref         0.1110
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All N(H,H) groups
 At 1.5 times of:
  All O(H) groups
2.a Free rotating group:
 O1(H1A)
2.b Rotating group:
 N10(H10A,H10B)
;
_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
O5 O 0.47710(19) 0.01597(9) 0.37355(11) 0.0292(3) Uani 1 1 d . . . . .
O1 O 0.6345(2) 0.76807(10) 0.40756(12) 0.0345(3) Uani 1 1 d . . . . .
H1A H 0.507420 0.765123 0.396308 0.052 Uiso 1 1 d G . . . .
O2 O 0.25062(18) 0.71669(10) 0.38610(11) 0.0344(3) Uani 1 1 d . . . . .
N3 N 0.79295(19) 0.41129(9) 0.37499(11) 0.0182(3) Uani 1 1 d . . . . .
N5 N 0.8308(2) 0.30700(9) 0.37354(11) 0.0193(3) Uani 1 1 d . . . . .
N1 N 0.7497(2) 0.57173(10) 0.37599(11) 0.0203(3) Uani 1 1 d . . . . .
N6 N 0.51613(19) 0.34029(10) 0.37583(11) 0.0194(3) Uani 1 1 d . . . . .
N7 N 0.3185(2) 0.33000(11) 0.37776(14) 0.0237(3) Uani 1 1 d . . . . .
N4 N 1.0734(2) 0.51525(11) 0.37380(12) 0.0230(3) Uani 1 1 d . . . . .
O4 O 0.1378(3) 0.87036(10) 0.35360(12) 0.0470(4) Uani 1 1 d . . . . .
N2 N 0.56619(19) 0.53038(10) 0.37883(11) 0.0211(3) Uani 1 1 d . . . . .
N8 N 0.4532(2) 0.11943(10) 0.37031(12) 0.0250(3) Uani 1 1 d . . . . .
O3 O -0.05228(18) 0.73834(12) 0.30568(13) 0.0435(4) Uani 1 1 d . . . . .
N10 N 0.9613(2) 0.08321(11) 0.38997(13) 0.0284(3) Uani 1 1 d . . . . .
H10A H 1.004246 0.025670 0.367961 0.034 Uiso 1 1 d GR . . . .
H10B H 0.984674 0.134379 0.349903 0.034 Uiso 1 1 d GR . . . .
N9 N 0.6720(2) -0.01096(10) 0.37944(12) 0.0267(3) Uani 1 1 d . . . . .
N11 N 0.1111(2) 0.77719(10) 0.34901(12) 0.0246(3) Uani 1 1 d . . . . .
C3 C 0.6594(2) 0.26765(11) 0.37407(12) 0.0180(3) Uani 1 1 d . . . . .
C1 C 0.8875(2) 0.50232(11) 0.37326(12) 0.0185(3) Uani 1 1 d . . . . .
C2 C 0.6055(2) 0.43319(11) 0.37756(12) 0.0182(3) Uani 1 1 d . . . . .
C4 C 0.6263(2) 0.15768(11) 0.37433(13) 0.0197(3) Uani 1 1 d . . . . .
C5 C 0.7659(2) 0.07590(12) 0.37995(13) 0.0214(3) Uani 1 1 d . . . . .
H4A H 1.116(3) 0.5798(18) 0.3697(16) 0.032(5) Uiso 1 1 d . . . . .
H4B H 1.148(3) 0.4612(18) 0.3717(16) 0.033(5) Uiso 1 1 d . . . . .
H1 H 0.757(3) 0.6425(19) 0.3748(17) 0.039(6) Uiso 1 1 d . . . . .
H1B H 0.667(3) 0.828(2) 0.3981(19) 0.044(7) Uiso 1 1 d . . . . .
H7A H 0.255(3) 0.2994(17) 0.3179(19) 0.039(6) Uiso 1 1 d . . . . .
H7B H 0.314(3) 0.2891(16) 0.4361(18) 0.034(6) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O5 N8 1.3592(17) . ?
O5 N9 1.3995(19) . ?
O1 H1A 0.8699 . ?
O1 H1B 0.83(3) . ?
O2 N11 1.2553(19) . ?
N3 N5 1.3872(17) . ?
N3 C1 1.3641(19) . ?
N3 C2 1.3581(19) . ?
N5 C3 1.313(2) . ?
N1 N2 1.4086(18) . ?
N1 C1 1.334(2) . ?
N1 H1 0.93(2) . ?
N6 N7 1.4036(18) . ?
N6 C3 1.3881(19) . ?
N6 C2 1.363(2) . ?
N7 H7A 0.88(2) . ?
N7 H7B 0.92(2) . ?
N4 C1 1.317(2) . ?
N4 H4A 0.90(2) . ?
N4 H4B 0.89(2) . ?
O4 N11 1.2288(19) . ?
N2 C2 1.299(2) . ?
N8 C4 1.306(2) . ?
O3 N11 1.2498(19) . ?
N10 H10A 0.8812 . ?
N10 H10B 0.8811 . ?
N10 C5 1.352(2) . ?
N9 C5 1.311(2) . ?
C3 C4 1.453(2) . ?
C4 C5 1.440(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N8 O5 N9 111.29(12) . . ?
H1A O1 H1B 109.2 . . ?
C1 N3 N5 139.20(13) . . ?
C2 N3 N5 113.44(12) . . ?
C2 N3 C1 107.36(12) . . ?
C3 N5 N3 101.72(12) . . ?
N2 N1 H1 116.1(14) . . ?
C1 N1 N2 114.75(13) . . ?
C1 N1 H1 129.2(14) . . ?
C3 N6 N7 131.47(13) . . ?
C2 N6 N7 122.70(12) . . ?
C2 N6 C3 105.82(12) . . ?
N6 N7 H7A 108.5(14) . . ?
N6 N7 H7B 107.8(13) . . ?
H7A N7 H7B 109(2) . . ?
C1 N4 H4A 117.8(13) . . ?
C1 N4 H4B 119.9(14) . . ?
H4A N4 H4B 122.0(19) . . ?
C2 N2 N1 99.99(12) . . ?
C4 N8 O5 105.72(13) . . ?
H10A N10 H10B 109.3 . . ?
C5 N10 H10A 109.4 . . ?
C5 N10 H10B 109.5 . . ?
C5 N9 O5 105.64(13) . . ?
O4 N11 O2 120.53(16) . . ?
O4 N11 O3 122.31(16) . . ?
O3 N11 O2 117.14(14) . . ?
N5 C3 N6 113.94(13) . . ?
N5 C3 C4 122.28(14) . . ?
N6 C3 C4 123.78(14) . . ?
N1 C1 N3 103.25(13) . . ?
N4 C1 N3 126.82(14) . . ?
N4 C1 N1 129.86(14) . . ?
N3 C2 N6 105.07(12) . . ?
N2 C2 N3 114.66(13) . . ?
N2 C2 N6 140.26(15) . . ?
N8 C4 C3 121.71(14) . . ?
N8 C4 C5 109.72(14) . . ?
C5 C4 C3 128.56(15) . . ?
N10 C5 C4 128.15(15) . . ?
N9 C5 N10 124.13(15) . . ?
N9 C5 C4 107.63(15) . . ?


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

data_mo_2021278_0m
_database_code_depnum_ccdc_archive 'CCDC 2078515'
loop_
_audit_author_name
_audit_author_address
'Caijin Lei'
;Nanjing University of Science and Technology
China
;
_audit_update_record             
;
2021-04-19 deposited with the CCDC.	2021-09-08 downloaded from the CCDC.
;
_audit_creation_date             2021-03-18
_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         'C5 H6 N10 O'
_chemical_formula_sum            'C5 H6 N10 O'
_chemical_formula_weight         222.20
_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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.8113(9)
_cell_length_b                   8.2072(10)
_cell_length_c                   8.5119(12)
_cell_angle_alpha                108.619(5)
_cell_angle_beta                 109.314(5)
_cell_angle_gamma                92.750(5)
_cell_volume                     419.23(10)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1467
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      26.381
_cell_measurement_theta_min      2.659
_shelx_estimated_absorpt_T_max   0.993
_shelx_estimated_absorpt_T_min   0.980
_exptl_absorpt_coefficient_mu    0.138
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6784
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0670 before and 0.0544 after correction. The Ratio of minimum to maximum transmission is 0.9101. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.760
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             228
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0468
_diffrn_reflns_av_unetI/netI     0.0580
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            4856
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.421
_diffrn_reflns_theta_min         2.658
_diffrn_ambient_temperature      170.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.988
_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                1207
_reflns_number_total             1710
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.249
_refine_diff_density_min         -0.246
_refine_diff_density_rms         0.056
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         1710
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0782
_refine_ls_R_factor_gt           0.0461
_refine_ls_restrained_S_all      1.031
_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)+(0.0474P)²+0.2140P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1013
_refine_ls_wR_factor_ref         0.1219
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All N(H,H) groups
2.a Rotating group:
 N9(H9A,H9B), N10(H10A,H10B)
;
_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
O1 O 0.4003(3) 0.0561(2) 0.8228(2) 0.0315(4) Uani 1 1 d . . . . .
N6 N 0.2390(3) 0.2496(2) 0.3927(2) 0.0214(4) Uani 1 1 d . . . . .
N4 N 0.5932(3) 0.2858(2) 0.4659(2) 0.0211(4) Uani 1 1 d . . . . .
N5 N 0.4922(3) 0.3354(2) 0.3221(2) 0.0197(4) Uani 1 1 d . . . . .
N8 N 0.3547(3) 0.4257(2) 0.1016(2) 0.0246(5) Uani 1 1 d . . . . .
N9 N 0.7360(3) 0.4581(2) 0.2198(2) 0.0250(5) Uani 1 1 d . . . . .
H9A H 0.811005 0.374996 0.230827 0.030 Uiso 1 1 d GR . . . .
H9B H 0.730001 0.477491 0.122337 0.030 Uiso 1 1 d GR . . . .
N7 N 0.1848(3) 0.3680(2) 0.1454(2) 0.0257(5) Uani 1 1 d . . . . .
N2 N 0.8593(3) 0.2043(3) 0.7786(3) 0.0312(5) Uani 1 1 d . . . . .
N3 N 0.3084(3) 0.1053(2) 0.6804(3) 0.0273(5) Uani 1 1 d . . . . .
N10 N 0.0360(3) 0.2199(3) 0.3943(3) 0.0328(5) Uani 1 1 d . . . . .
H10A H -0.001770 0.107560 0.369641 0.039 Uiso 1 1 d GR . . . .
H10B H 0.036004 0.279144 0.500915 0.039 Uiso 1 1 d GR . . . .
N1 N 0.6214(3) 0.0893(3) 0.8792(3) 0.0297(5) Uani 1 1 d . . . . .
C4 C 0.2805(3) 0.3157(3) 0.2760(3) 0.0208(5) Uani 1 1 d . . . . .
C3 C 0.4335(3) 0.2345(3) 0.5032(3) 0.0193(5) Uani 1 1 d . . . . .
C1 C 0.6611(3) 0.1592(3) 0.7722(3) 0.0234(5) Uani 1 1 d . . . . .
C2 C 0.4640(3) 0.1686(3) 0.6476(3) 0.0205(5) Uani 1 1 d . . . . .
C5 C 0.5355(3) 0.4054(3) 0.2079(3) 0.0214(5) Uani 1 1 d . . . . .
H2A H 0.961(4) 0.231(3) 0.886(4) 0.045(8) Uiso 1 1 d . . . . .
H2B H 0.869(4) 0.276(3) 0.721(4) 0.041(8) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 N3 1.364(2) . ?
O1 N1 1.404(2) . ?
N6 N10 1.398(2) . ?
N6 C4 1.370(3) . ?
N6 C3 1.386(3) . ?
N4 N5 1.387(2) . ?
N4 C3 1.316(3) . ?
N5 C4 1.350(3) . ?
N5 C5 1.376(3) . ?
N8 N7 1.430(3) . ?
N8 C5 1.320(3) . ?
N9 H9A 0.8820 . ?
N9 H9B 0.8821 . ?
N9 C5 1.373(3) . ?
N7 C4 1.303(3) . ?
N2 C1 1.362(3) . ?
N2 H2A 0.90(3) . ?
N2 H2B 0.89(3) . ?
N3 C2 1.306(3) . ?
N10 H10A 0.8819 . ?
N10 H10B 0.8820 . ?
N1 C1 1.308(3) . ?
C3 C2 1.453(3) . ?
C1 C2 1.433(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N3 O1 N1 111.03(16) . . ?
C4 N6 N10 122.63(17) . . ?
C4 N6 C3 105.74(17) . . ?
C3 N6 N10 131.49(18) . . ?
C3 N4 N5 101.96(16) . . ?
C4 N5 N4 113.42(17) . . ?
C4 N5 C5 105.56(17) . . ?
C5 N5 N4 140.99(18) . . ?
C5 N8 N7 109.80(17) . . ?
H9A N9 H9B 109.2 . . ?
C5 N9 H9A 109.1 . . ?
C5 N9 H9B 109.5 . . ?
C4 N7 N8 102.99(17) . . ?
C1 N2 H2A 114.4(18) . . ?
C1 N2 H2B 114.5(17) . . ?
H2A N2 H2B 115(2) . . ?
C2 N3 O1 105.79(17) . . ?
N6 N10 H10A 109.2 . . ?
N6 N10 H10B 109.4 . . ?
H10A N10 H10B 109.2 . . ?
C1 N1 O1 105.27(17) . . ?
N5 C4 N6 105.23(17) . . ?
N7 C4 N6 140.8(2) . . ?
N7 C4 N5 113.91(19) . . ?
N6 C3 C2 124.53(19) . . ?
N4 C3 N6 113.65(18) . . ?
N4 C3 C2 121.83(18) . . ?
N2 C1 C2 128.0(2) . . ?
N1 C1 N2 123.6(2) . . ?
N1 C1 C2 108.4(2) . . ?
N3 C2 C3 123.40(19) . . ?
N3 C2 C1 109.54(19) . . ?
C1 C2 C3 127.1(2) . . ?
N5 C5 N9 123.90(19) . . ?
N8 C5 N5 107.75(19) . . ?
N8 C5 N9 128.1(2) . . ?


_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_lcj
_database_code_depnum_ccdc_archive 'CCDC 2078516'
loop_
_audit_author_name
_audit_author_address
'Caijin Lei'
;Nanjing University of Science and Technology
China
;
_audit_update_record             
;
2021-04-19 deposited with the CCDC.	2021-09-08 downloaded from the CCDC.
;
_audit_creation_date             2020-11-23
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(N O3), C5 H9 N11, H2 O'
_chemical_formula_sum            'C5 H11 N13 O7'
_chemical_formula_weight         365.27
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   6.5824(11)
_cell_length_b                   9.6308(11)
_cell_length_c                   11.1986(16)
_cell_angle_alpha                77.516(4)
_cell_angle_beta                 75.288(4)
_cell_angle_gamma                89.243(3)
_cell_volume                     669.76(17)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2571
_cell_measurement_temperature    160
_cell_measurement_theta_max      26.226
_cell_measurement_theta_min      2.168
_shelx_estimated_absorpt_T_max   0.994
_shelx_estimated_absorpt_T_min   0.974
_exptl_absorpt_coefficient_mu    0.163
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6596
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1258 before and 0.0630 after correction. The Ratio of minimum to maximum transmission is 0.8849. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.811
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             376
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.04
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0576
_diffrn_reflns_av_unetI/netI     0.0762
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            7581
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.445
_diffrn_reflns_theta_min         1.927
_diffrn_ambient_temperature      160.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1793
_reflns_number_total             2733
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_refine_diff_density_max         0.606
_refine_diff_density_min         -0.356
_refine_diff_density_rms         0.100
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     241
_refine_ls_number_reflns         2733
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1151
_refine_ls_R_factor_gt           0.0720
_refine_ls_restrained_S_all      1.049
_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)+(0.1169P)²+0.3698P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1770
_refine_ls_wR_factor_ref         0.2144
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All N(H) groups, All N(H,H) groups
 At 1.5 times of:
  All O(H,H) groups
2. Restrained distances
 N7-H7B \\sim N7-H7A
 with sigma of 0.02
3.a Free rotating group:
 O1(H1A,H1B)
3.b Aromatic/amide H refined with riding coordinates:
 N8(H8), N10(H10)
3.c X=CH2 refined with riding coordinates:
 N3(H3A,H3B), N11(H11A,H11B)
;
_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
O7 O 0.0460(4) 0.4868(3) 0.8479(2) 0.0314(7) Uani 1 1 d . . . . .
O2 O 0.6976(5) 0.0250(3) 0.1805(3) 0.0359(7) Uani 1 1 d . . . . .
O5 O 0.1857(5) 0.3630(3) 0.7095(3) 0.0383(8) Uani 1 1 d . . . . .
O6 O 0.1113(5) 0.5822(3) 0.6471(3) 0.0396(8) Uani 1 1 d . . . . .
O3 O 0.5772(5) 0.1032(3) 0.3514(3) 0.0372(8) Uani 1 1 d . . . . .
O4 O 0.7525(5) -0.0883(3) 0.3588(3) 0.0411(8) Uani 1 1 d . . . . .
N4 N 0.2117(5) 1.0268(3) 0.1470(3) 0.0213(7) Uani 1 1 d . . . . .
N8 N 0.2950(5) 0.5878(3) 0.3812(3) 0.0220(7) Uani 1 1 d . . . . .
H8 H 0.243960 0.611324 0.454399 0.026 Uiso 1 1 calc R . . . .
N6 N 0.2259(5) 0.9019(3) 0.3290(3) 0.0228(7) Uani 1 1 d . . . . .
N10 N 0.4219(5) 0.4708(3) 0.2380(3) 0.0241(7) Uani 1 1 d . . . . .
H10 H 0.470138 0.401058 0.200730 0.029 Uiso 1 1 calc R . . . .
O1 O 0.5985(6) 0.3017(3) 0.0908(3) 0.0463(9) Uani 1 1 d . . . . .
H1A H 0.609518 0.313923 0.010096 0.069 Uiso 1 1 d G . . . .
H1B H 0.624349 0.212524 0.114506 0.069 Uiso 1 1 d G . . . .
N5 N 0.2701(5) 0.8941(3) 0.1229(3) 0.0225(7) Uani 1 1 d . . . . .
N2 N 0.0980(5) 1.2269(4) 0.1748(3) 0.0247(7) Uani 1 1 d . . . . .
N9 N 0.4038(5) 0.6076(3) 0.1745(3) 0.0239(7) Uani 1 1 d . . . . .
N12 N 0.1158(5) 0.4778(4) 0.7341(3) 0.0257(8) Uani 1 1 d . . . . .
N1 N 0.1141(5) 1.1538(3) 0.2950(3) 0.0250(7) Uani 1 1 d . . . . .
N13 N 0.6756(5) 0.0124(4) 0.2982(3) 0.0275(8) Uani 1 1 d . . . . .
N3 N 0.1544(5) 1.1888(4) -0.0349(3) 0.0278(8) Uani 1 1 d . . . . .
H3A H 0.112673 1.272965 -0.066053 0.033 Uiso 1 1 calc R . . . .
H3B H 0.196357 1.128571 -0.084142 0.033 Uiso 1 1 calc R . . . .
N7 N 0.2101(6) 0.8465(4) 0.4575(3) 0.0282(8) Uani 1 1 d D . . . .
N11 N 0.3521(5) 0.3432(3) 0.4522(3) 0.0301(8) Uani 1 1 d . . . . .
H11A H 0.395153 0.262191 0.432534 0.036 Uiso 1 1 calc R . . . .
H11B H 0.305482 0.347835 0.532131 0.036 Uiso 1 1 calc R . . . .
C2 C 0.1804(6) 1.0344(4) 0.2705(3) 0.0222(8) Uani 1 1 d . . . . .
C4 C 0.3277(6) 0.6756(4) 0.2629(3) 0.0207(8) Uani 1 1 d . . . . .
C1 C 0.1542(6) 1.1535(4) 0.0844(3) 0.0221(8) Uani 1 1 d . . . . .
C5 C 0.3575(6) 0.4572(4) 0.3624(3) 0.0230(8) Uani 1 1 d . . . . .
C3 C 0.2761(6) 0.8234(4) 0.2371(3) 0.0210(8) Uani 1 1 d . . . . .
H2 H 0.049(6) 1.321(5) 0.162(4) 0.031(11) Uiso 1 1 d . . . . .
H7A H 0.078(5) 0.845(5) 0.503(4) 0.036(12) Uiso 1 1 d D . . . .
H7B H 0.303(7) 0.898(5) 0.478(5) 0.059(17) 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
O7 N12 1.262(4) . ?
O2 N13 1.268(4) . ?
O5 N12 1.250(4) . ?
O6 N12 1.246(4) . ?
O3 N13 1.246(4) . ?
O4 N13 1.238(4) . ?
N4 N5 1.392(4) . ?
N4 C2 1.363(4) . ?
N4 C1 1.370(5) . ?
N8 H8 0.8800 . ?
N8 C4 1.376(5) . ?
N8 C5 1.361(5) . ?
N6 N7 1.399(4) . ?
N6 C2 1.369(5) . ?
N6 C3 1.377(4) . ?
N10 H10 0.8800 . ?
N10 N9 1.374(4) . ?
N10 C5 1.327(5) . ?
O1 H1A 0.8701 . ?
O1 H1B 0.8699 . ?
N5 C3 1.322(5) . ?
N2 N1 1.407(4) . ?
N2 C1 1.332(5) . ?
N2 H2 0.95(4) . ?
N9 C4 1.296(5) . ?
N1 C2 1.285(5) . ?
N3 H3A 0.8800 . ?
N3 H3B 0.8800 . ?
N3 C1 1.304(5) . ?
N7 H7A 0.89(3) . ?
N7 H7B 0.90(3) . ?
N11 H11A 0.8800 . ?
N11 H11B 0.8800 . ?
N11 C5 1.313(5) . ?
C4 C3 1.444(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
C2 N4 N5 114.2(3) . . ?
C2 N4 C1 107.1(3) . . ?
C1 N4 N5 138.2(3) . . ?
C4 N8 H8 126.9 . . ?
C5 N8 H8 126.9 . . ?
C5 N8 C4 106.2(3) . . ?
C2 N6 N7 129.2(3) . . ?
C2 N6 C3 106.4(3) . . ?
C3 N6 N7 124.2(3) . . ?
N9 N10 H10 124.2 . . ?
C5 N10 H10 124.2 . . ?
C5 N10 N9 111.5(3) . . ?
H1A O1 H1B 104.5 . . ?
C3 N5 N4 100.8(3) . . ?
N1 N2 H2 121(3) . . ?
C1 N2 N1 114.7(3) . . ?
C1 N2 H2 124(3) . . ?
C4 N9 N10 104.7(3) . . ?
O5 N12 O7 119.6(3) . . ?
O6 N12 O7 120.0(3) . . ?
O6 N12 O5 120.4(3) . . ?
C2 N1 N2 100.5(3) . . ?
O3 N13 O2 119.0(3) . . ?
O4 N13 O2 120.2(3) . . ?
O4 N13 O3 120.8(3) . . ?
H3A N3 H3B 120.0 . . ?
C1 N3 H3A 120.0 . . ?
C1 N3 H3B 120.0 . . ?
N6 N7 H7A 111(3) . . ?
N6 N7 H7B 106(3) . . ?
H7A N7 H7B 116(4) . . ?
H11A N11 H11B 120.0 . . ?
C5 N11 H11A 120.0 . . ?
C5 N11 H11B 120.0 . . ?
N4 C2 N6 104.1(3) . . ?
N1 C2 N4 114.6(3) . . ?
N1 C2 N6 141.2(3) . . ?
N8 C4 C3 125.4(3) . . ?
N9 C4 N8 111.5(3) . . ?
N9 C4 C3 123.0(3) . . ?
N2 C1 N4 103.0(3) . . ?
N3 C1 N4 127.0(3) . . ?
N3 C1 N2 130.0(4) . . ?
N10 C5 N8 106.1(3) . . ?
N11 C5 N8 125.3(3) . . ?
N11 C5 N10 128.6(3) . . ?
N6 C3 C4 123.1(3) . . ?
N5 C3 N6 114.4(3) . . ?
N5 C3 C4 122.5(3) . . ?


_olex2_submission_special_instructions 'No special instructions were received'
