# Electronic Supplementary Material (ESI) for CrystEngComm.
# 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_180606_s2_cd_180530-1
_database_code_depnum_ccdc_archive 'CCDC 1851336'
loop_
_audit_author_name
_audit_author_address
'DONG CHEN'
;China Academy of Engineering Physics
China
;
_audit_update_record             
;
2018-06-25 deposited with the CCDC.	2019-12-03 downloaded from the CCDC.
;
_audit_creation_date             2018-06-11
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            CBNT
_chemical_name_systematic        
'carbohydrazide bis[3-(5-nitroimino-1,2,4-triazolate)]'
_chemical_formula_moiety         'C4 H2 N10 O4, C H8 N4 O, 2(H2 O)'
_chemical_formula_sum            'C5 H14 N14 O7'
_chemical_formula_weight         382.30
_chemical_melting_point          ?
_chemical_oxdiff_formula         c12h12n2o3
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                   6.5011(8)
_cell_length_b                   10.2497(12)
_cell_length_c                   11.0964(13)
_cell_angle_alpha                97.740(10)
_cell_angle_beta                 99.840(11)
_cell_angle_gamma                90.131(10)
_cell_volume                     721.65(15)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1139
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.7250
_cell_measurement_theta_min      3.7390
_shelx_estimated_absorpt_T_max   0.992
_shelx_estimated_absorpt_T_min   0.947
_exptl_absorpt_coefficient_mu    0.157
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.29988
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.759
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             396
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.05
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0306
_diffrn_reflns_av_unetI/netI     0.0817
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.833
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            5609
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.833
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.323
_diffrn_reflns_theta_min         2.932
_diffrn_ambient_temperature      293.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0874
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.833
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -83.00   11.40   0.8000   75.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.9669  -77.0000  -60.0000 118

#__ type_ start__ end____ width___ exp.time_
  2 omega  -42.00   52.40   0.8000   75.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.9669   77.0000   60.0000 118

#__ type_ start__ end____ width___ exp.time_
  3 omega  -87.00  -35.00   0.8000   75.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.9669 -178.0000   90.0000 65

#__ type_ start__ end____ width___ exp.time_
  4 omega  -15.00   19.40   0.8000   75.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.9669  -99.0000 -180.0000 43

#__ type_ start__ end____ width___ exp.time_
  5 omega    1.00   61.00   0.8000   75.0000
omega____ theta____ kappa____ phi______ frames
    -       16.6856   38.0000 -150.0000 75
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0470816000
_diffrn_orient_matrix_UB_12      0.0637561000
_diffrn_orient_matrix_UB_13      0.0175623000
_diffrn_orient_matrix_UB_21      -0.0421779000
_diffrn_orient_matrix_UB_22      0.0171350000
_diffrn_orient_matrix_UB_23      -0.0588989000
_diffrn_orient_matrix_UB_31      -0.0909627000
_diffrn_orient_matrix_UB_32      0.0228484000
_diffrn_orient_matrix_UB_33      0.0226231000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2023
_reflns_number_total             3290
_reflns_odcompleteness_completeness 98.51
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_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    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.335
_refine_diff_density_min         -0.351
_refine_diff_density_rms         0.077
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     273
_refine_ls_number_reflns         3290
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1036
_refine_ls_R_factor_gt           0.0597
_refine_ls_restrained_S_all      1.054
_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)+(0.0658P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1394
_refine_ls_wR_factor_ref         0.1664
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All N(H) groups
 At 1.5 times of:
  All O(H,H) groups
2.a Free rotating group:
 O6(H6A,H6B), O7(H7A,H7B)
2.b Aromatic/amide H refined with riding coordinates:
 N12(H12), N13(H13)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_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 0.8192(4) 1.1185(2) 0.8178(2) 0.0374(6) Uani 1 1 d . . . . .
O2 O 0.7870(5) 1.0828(2) 0.6173(2) 0.0509(7) Uani 1 1 d . . . . .
O3 O 0.6567(4) 0.0297(2) 0.1537(2) 0.0458(7) Uani 1 1 d . . . . .
O4 O 0.7224(4) 0.0652(2) 0.3545(2) 0.0448(7) Uani 1 1 d . . . . .
N1 N 0.7703(4) 0.6982(2) 0.6256(2) 0.0219(6) Uani 1 1 d . . . . .
N2 N 0.7469(4) 0.8481(3) 0.5012(2) 0.0272(6) Uani 1 1 d . . . . .
H2 H 0.740(6) 0.922(4) 0.470(4) 0.063(13) Uiso 1 1 d . . . . .
N3 N 0.7276(4) 0.7309(2) 0.4265(2) 0.0276(6) Uani 1 1 d . . . . .
N4 N 0.7951(4) 0.9141(2) 0.7275(2) 0.0263(6) Uani 1 1 d . . . . .
N5 N 0.7992(4) 1.0400(3) 0.7182(2) 0.0293(6) Uani 1 1 d . . . . .
N6 N 0.6989(4) 0.4497(2) 0.3439(2) 0.0235(6) Uani 1 1 d . . . . .
N7 N 0.7503(4) 0.3012(2) 0.4692(2) 0.0237(6) Uani 1 1 d . . . . .
H7 H 0.762(5) 0.229(3) 0.501(3) 0.030(9) Uiso 1 1 d . . . . .
N8 N 0.7675(4) 0.4183(2) 0.5446(2) 0.0253(6) Uani 1 1 d . . . . .
N9 N 0.6799(4) 0.2338(2) 0.2421(2) 0.0269(6) Uani 1 1 d . . . . .
N10 N 0.6879(4) 0.1071(3) 0.2527(3) 0.0304(6) Uani 1 1 d . . . . .
C8 C 0.7430(4) 0.6448(3) 0.5056(3) 0.0210(6) Uani 1 1 d . . . . .
C10 C 0.7703(4) 0.8279(3) 0.6197(3) 0.0224(7) Uani 1 1 d . . . . .
C13 C 0.7359(4) 0.5039(3) 0.4648(3) 0.0212(6) Uani 1 1 d . . . . .
C15 C 0.7103(4) 0.3204(3) 0.3500(3) 0.0200(6) Uani 1 1 d . . . . .
O5 O 0.1683(3) 0.6214(2) 0.0175(2) 0.0333(6) Uani 1 1 d . . . . .
N11 N 0.4836(5) 0.7818(3) 0.0183(3) 0.0324(7) Uani 1 1 d . . . . .
H11A H 0.637(6) 0.808(3) 0.006(3) 0.051(11) Uiso 1 1 d . . . . .
H11B H 0.424(7) 0.854(5) 0.072(5) 0.107(19) Uiso 1 1 d . . . . .
H11C H 0.401(7) 0.759(4) -0.062(4) 0.071(13) Uiso 1 1 d . . . . .
N12 N 0.5103(4) 0.6698(3) 0.0803(3) 0.0375(7) Uani 1 1 d . . . . .
H12 H 0.6311 0.6456 0.1135 0.045 Uiso 1 1 calc R . . . .
N13 N 0.3511(4) 0.5131(3) 0.1636(3) 0.0370(7) Uani 1 1 d . . . . .
H13 H 0.4705 0.4923 0.2017 0.044 Uiso 1 1 calc R . . . .
N14 N 0.1619(5) 0.4554(3) 0.1802(3) 0.0300(7) Uani 1 1 d . . . . .
H14A H 0.185(5) 0.393(3) 0.241(4) 0.046(10) Uiso 1 1 d . . . . .
H14B H 0.045(6) 0.525(4) 0.189(4) 0.059(12) Uiso 1 1 d . . . . .
H14C H 0.103(6) 0.403(4) 0.117(4) 0.051(12) Uiso 1 1 d . . . . .
C3 C 0.3321(5) 0.6035(3) 0.0837(3) 0.0273(7) Uani 1 1 d . . . . .
O6 O 0.9126(4) 0.6751(2) 0.2147(2) 0.0353(6) Uani 1 1 d . . . . .
H6A H 1.0007 0.7363 0.2139 0.053 Uiso 1 1 d G . . . .
H6B H 0.8713 0.6845 0.2839 0.053 Uiso 1 1 d G . . . .
O7 O 0.1441(4) 0.1733(2) 0.0422(2) 0.0414(7) Uani 1 1 d . . . . .
H7A H 0.1536 0.1342 0.1057 0.062 Uiso 1 1 d G . . . .
H7B H 0.0484 0.1361 -0.0139 0.062 Uiso 1 1 d G . . . .


_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 N5 1.263(3) . ?
O2 N5 1.247(3) . ?
O3 N10 1.252(3) . ?
O4 N10 1.247(3) . ?
N1 C8 1.352(4) . ?
N1 C10 1.340(4) . ?
N2 H2 0.87(4) . ?
N2 N3 1.357(3) . ?
N2 C10 1.341(4) . ?
N3 C8 1.318(4) . ?
N4 N5 1.309(3) . ?
N4 C10 1.374(4) . ?
N6 C13 1.362(4) . ?
N6 C15 1.338(4) . ?
N7 H7 0.86(3) . ?
N7 N8 1.361(3) . ?
N7 C15 1.344(4) . ?
N8 C13 1.320(4) . ?
N9 N10 1.321(3) . ?
N9 C15 1.376(4) . ?
C8 C13 1.453(4) . ?
O5 C3 1.216(4) . ?
N11 H11A 1.07(3) . ?
N11 H11B 1.01(5) . ?
N11 H11C 0.96(5) . ?
N11 N12 1.412(4) . ?
N12 H12 0.8600 . ?
N12 C3 1.351(4) . ?
N13 H13 0.8600 . ?
N13 N14 1.414(3) . ?
N13 C3 1.358(4) . ?
N14 H14A 0.98(4) . ?
N14 H14B 1.05(4) . ?
N14 H14C 0.86(4) . ?
O6 H6A 0.8504 . ?
O6 H6B 0.8495 . ?
O7 H7A 0.8501 . ?
O7 H7B 0.8500 . ?

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 N1 C8 103.0(2) . . ?
N3 N2 H2 120(3) . . ?
C10 N2 H2 130(3) . . ?
C10 N2 N3 109.9(2) . . ?
C8 N3 N2 102.8(2) . . ?
N5 N4 C10 117.2(2) . . ?
O1 N5 N4 116.7(3) . . ?
O2 N5 O1 120.5(3) . . ?
O2 N5 N4 122.8(3) . . ?
C15 N6 C13 103.1(2) . . ?
N8 N7 H7 120(2) . . ?
C15 N7 H7 130(2) . . ?
C15 N7 N8 110.6(2) . . ?
C13 N8 N7 102.2(2) . . ?
N10 N9 C15 116.8(3) . . ?
O3 N10 N9 116.0(3) . . ?
O4 N10 O3 121.2(3) . . ?
O4 N10 N9 122.8(3) . . ?
N1 C8 C13 123.5(3) . . ?
N3 C8 N1 114.8(3) . . ?
N3 C8 C13 121.7(3) . . ?
N1 C10 N2 109.5(3) . . ?
N1 C10 N4 118.9(3) . . ?
N2 C10 N4 131.6(3) . . ?
N6 C13 C8 123.6(3) . . ?
N8 C13 N6 115.0(3) . . ?
N8 C13 C8 121.4(3) . . ?
N6 C15 N7 109.1(3) . . ?
N6 C15 N9 119.0(3) . . ?
N7 C15 N9 131.9(3) . . ?
H11A N11 H11B 111(3) . . ?
H11A N11 H11C 107(3) . . ?
H11B N11 H11C 114(4) . . ?
N12 N11 H11A 104.6(19) . . ?
N12 N11 H11B 109(3) . . ?
N12 N11 H11C 110(2) . . ?
N11 N12 H12 122.5 . . ?
C3 N12 N11 115.0(3) . . ?
C3 N12 H12 122.5 . . ?
N14 N13 H13 122.1 . . ?
C3 N13 H13 122.1 . . ?
C3 N13 N14 115.7(3) . . ?
N13 N14 H14A 112.2(19) . . ?
N13 N14 H14B 112(2) . . ?
N13 N14 H14C 113(2) . . ?
H14A N14 H14B 117(3) . . ?
H14A N14 H14C 100(3) . . ?
H14B N14 H14C 101(3) . . ?
O5 C3 N12 122.2(3) . . ?
O5 C3 N13 122.7(3) . . ?
N12 C3 N13 115.1(3) . . ?
H6A O6 H6B 109.5 . . ?
H7A O7 H7B 109.5 . . ?

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
N1 C8 C13 N6 176.8(3) . . . . ?
N1 C8 C13 N8 -3.7(4) . . . . ?
N2 N3 C8 N1 0.2(3) . . . . ?
N2 N3 C8 C13 -178.4(3) . . . . ?
N3 N2 C10 N1 0.9(3) . . . . ?
N3 N2 C10 N4 -179.9(3) . . . . ?
N3 C8 C13 N6 -4.7(4) . . . . ?
N3 C8 C13 N8 174.7(3) . . . . ?
N5 N4 C10 N1 178.5(2) . . . . ?
N5 N4 C10 N2 -0.6(5) . . . . ?
N7 N8 C13 N6 0.3(3) . . . . ?
N7 N8 C13 C8 -179.2(2) . . . . ?
N8 N7 C15 N6 -0.4(3) . . . . ?
N8 N7 C15 N9 -179.7(3) . . . . ?
N10 N9 C15 N6 -178.5(2) . . . . ?
N10 N9 C15 N7 0.8(5) . . . . ?
C8 N1 C10 N2 -0.8(3) . . . . ?
C8 N1 C10 N4 180.0(2) . . . . ?
C10 N1 C8 N3 0.4(3) . . . . ?
C10 N1 C8 C13 178.9(3) . . . . ?
C10 N2 N3 C8 -0.7(3) . . . . ?
C10 N4 N5 O1 179.1(2) . . . . ?
C10 N4 N5 O2 -1.9(4) . . . . ?
C13 N6 C15 N7 0.6(3) . . . . ?
C13 N6 C15 N9 180.0(2) . . . . ?
C15 N6 C13 N8 -0.6(3) . . . . ?
C15 N6 C13 C8 178.9(2) . . . . ?
C15 N7 N8 C13 0.1(3) . . . . ?
C15 N9 N10 O3 179.0(2) . . . . ?
C15 N9 N10 O4 -0.4(4) . . . . ?
N11 N12 C3 O5 14.7(5) . . . . ?
N11 N12 C3 N13 -167.1(3) . . . . ?
N14 N13 C3 O5 -9.8(5) . . . . ?
N14 N13 C3 N12 172.0(3) . . . . ?

_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_d8v18509_0m
_database_code_depnum_ccdc_archive 'CCDC 1917976'
loop_
_audit_author_name
_audit_author_address
'DONG CHEN'
;China Academy of Engineering Physics
China
;
_audit_update_record             
;
2019-05-23 deposited with the CCDC.	2019-12-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '[NH2(CH3)2+]2[BNT2-].2H2O'
_chemical_formula_sum            'C8 H22 N12 O6'
_chemical_formula_weight         382.37

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.0311(2)
_cell_length_b                   6.9489(2)
_cell_length_c                   11.1061(4)
_cell_angle_alpha                77.4370(10)
_cell_angle_beta                 89.7860(10)
_cell_angle_gamma                75.1460(10)
_cell_volume                     438.46(3)
_cell_formula_units_Z            1
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3725
_cell_measurement_theta_min      6.511
_cell_measurement_theta_max      54.764

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.448
_exptl_crystal_F_000             202
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.170
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.122
_shelx_estimated_absorpt_T_min   0.980
_shelx_estimated_absorpt_T_max   0.988
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6899
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6244
_diffrn_reflns_av_unetI/netI     0.0243
_diffrn_reflns_av_R_equivalents  0.0281
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.112
_diffrn_reflns_theta_max         25.998
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measured_fraction_theta_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_point_group_measured_fraction_full 0.982
_reflns_number_total             1703
_reflns_number_gt                1523
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 ? 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0460P)²+0.1049P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       ?
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         1703
_refine_ls_number_parameters     163
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0396
_refine_ls_R_factor_gt           0.0353
_refine_ls_wR_factor_ref         0.0947
_refine_ls_wR_factor_gt          0.0905
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_restrained_S_all      1.027
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.0957(2) 0.41217(19) 0.61783(11) 0.0685(4) Uani 1 1 d . . . . .
O2 O 0.27687(19) 0.19840(15) 0.78004(10) 0.0501(3) Uani 1 1 d . . . . .
N1 N 0.50996(18) 0.76645(16) 0.62076(9) 0.0346(3) Uani 1 1 d . . . . .
N2 N 0.2885(2) 0.89201(17) 0.44392(10) 0.0403(3) Uani 1 1 d . . . . .
N3 N 0.2448(2) 0.71653(17) 0.50790(10) 0.0379(3) Uani 1 1 d . . . . .
H3 H 0.147(3) 0.672(3) 0.4816(15) 0.049(5) Uiso 1 1 d . . . . .
N4 N 0.40019(19) 0.46761(16) 0.70409(10) 0.0362(3) Uani 1 1 d . . . . .
N5 N 0.25506(19) 0.35908(16) 0.69798(10) 0.0365(3) Uani 1 1 d . . . . .
C1 C 0.4483(2) 0.91411(19) 0.51586(11) 0.0325(3) Uani 1 1 d . . . . .
C2 C 0.3776(2) 0.64263(18) 0.61280(11) 0.0307(3) Uani 1 1 d . . . . .
O3 O 0.8017(2) 0.22751(19) 0.85626(11) 0.0551(3) Uani 1 1 d . . . . .
H3D H 0.686(4) 0.309(3) 0.806(2) 0.084(7) Uiso 1 1 d . . . . .
H3E H 0.926(4) 0.234(3) 0.819(2) 0.080(7) Uiso 1 1 d . . . . .
N6 N 0.7208(2) 0.84591(19) 0.82876(11) 0.0396(3) Uani 1 1 d . . . . .
H6A H 0.708(3) 0.979(3) 0.8281(17) 0.062(5) Uiso 1 1 d . . . . .
H6B H 0.659(3) 0.835(3) 0.7615(19) 0.062(5) Uiso 1 1 d . . . . .
C3 C 0.9680(3) 0.7499(4) 0.8370(2) 0.0696(6) Uani 1 1 d . . . . .
H3A H 1.037(4) 0.768(4) 0.911(2) 0.100(8) Uiso 1 1 d . . . . .
H3B H 0.984(5) 0.611(4) 0.840(3) 0.116(10) Uiso 1 1 d . . . . .
H3C H 1.032(4) 0.822(4) 0.767(2) 0.100(8) Uiso 1 1 d . . . . .
C4 C 0.5974(4) 0.7548(3) 0.92983(17) 0.0571(5) Uani 1 1 d . . . . .
H4A H 0.668(4) 0.760(3) 1.005(2) 0.081(6) Uiso 1 1 d . . . . .
H4B H 0.615(4) 0.621(4) 0.930(2) 0.079(6) Uiso 1 1 d . . . . .
H4C H 0.440(4) 0.824(3) 0.922(2) 0.089(7) 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 N5 1.2387(15) . ?
O2 N5 1.2560(14) . ?
N1 C2 1.3310(16) . ?
N1 C1 1.3549(16) . ?
N2 C1 1.3141(16) . ?
N2 N3 1.3593(15) . ?
N3 C2 1.3410(17) . ?
N3 H3 0.810(18) . ?
N4 N5 1.3041(15) . ?
N4 C2 1.3803(16) . ?
C1 C1 1.461(2) 2_676 ?
O3 H3D 0.88(2) . ?
O3 H3E 0.86(2) . ?
N6 C4 1.463(2) . ?
N6 C3 1.463(2) . ?
N6 H6A 0.91(2) . ?
N6 H6B 0.86(2) . ?
C3 H3A 0.96(3) . ?
C3 H3B 0.94(3) . ?
C3 H3C 0.97(3) . ?
C4 H4A 0.95(2) . ?
C4 H4B 0.91(2) . ?
C4 H4C 0.94(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
C2 N1 C1 103.12(10) . . ?
C1 N2 N3 102.02(10) . . ?
C2 N3 N2 110.55(10) . . ?
C2 N3 H3 129.3(12) . . ?
N2 N3 H3 120.2(12) . . ?
N5 N4 C2 117.23(11) . . ?
O1 N5 O2 119.94(11) . . ?
O1 N5 N4 122.61(11) . . ?
O2 N5 N4 117.42(11) . . ?
N2 C1 N1 115.21(11) . . ?
N2 C1 C1 122.05(14) . 2_676 ?
N1 C1 C1 122.74(14) . 2_676 ?
N1 C2 N3 109.10(11) . . ?
N1 C2 N4 119.23(11) . . ?
N3 C2 N4 131.63(11) . . ?
H3D O3 H3E 107(2) . . ?
C4 N6 C3 113.96(16) . . ?
C4 N6 H6A 110.8(12) . . ?
C3 N6 H6A 105.3(12) . . ?
C4 N6 H6B 106.4(13) . . ?
C3 N6 H6B 110.2(12) . . ?
H6A N6 H6B 110.2(17) . . ?
N6 C3 H3A 109.7(14) . . ?
N6 C3 H3B 106.1(18) . . ?
H3A C3 H3B 111(2) . . ?
N6 C3 H3C 107.0(15) . . ?
H3A C3 H3C 107(2) . . ?
H3B C3 H3C 116(2) . . ?
N6 C4 H4A 107.3(13) . . ?
N6 C4 H4B 109.3(14) . . ?
H4A C4 H4B 107.4(18) . . ?
N6 C4 H4C 111.1(14) . . ?
H4A C4 H4C 111.8(19) . . ?
H4B C4 H4C 110(2) . . ?

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
C1 N2 N3 C2 -0.13(15) . . . . ?
C2 N4 N5 O1 -3.21(19) . . . . ?
C2 N4 N5 O2 179.15(11) . . . . ?
N3 N2 C1 N1 -0.02(15) . . . . ?
N3 N2 C1 C1 179.85(15) . . . 2_676 ?
C2 N1 C1 N2 0.16(15) . . . . ?
C2 N1 C1 C1 -179.72(15) . . . 2_676 ?
C1 N1 C2 N3 -0.23(14) . . . . ?
C1 N1 C2 N4 177.81(11) . . . . ?
N2 N3 C2 N1 0.23(15) . . . . ?
N2 N3 C2 N4 -177.48(13) . . . . ?
N5 N4 C2 N1 174.70(11) . . . . ?
N5 N4 C2 N3 -7.8(2) . . . . ?

_refine_diff_density_max         0.276
_refine_diff_density_min         -0.182
_refine_diff_density_rms         0.029

_shelxl_version_number           2013-4


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
####################################################################### 
# 
# 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_d8v18635_0m
_database_code_depnum_ccdc_archive 'CCDC 1918102'
loop_
_audit_author_name
_audit_author_address
'DONG CHEN'
;China Academy of Engineering Physics
China
;
_audit_update_record             
;
2019-08-18 deposited with the CCDC.	2019-12-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C4 H4 N10 O4, 2(H2 O)'
_chemical_formula_sum            'C4 H8 N10 O6'
_chemical_formula_weight         292.20

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   5.2460(2)
_cell_length_b                   17.8848(7)
_cell_length_c                   6.3117(2)
_cell_angle_alpha                90
_cell_angle_beta                 112.398(2)
_cell_angle_gamma                90
_cell_volume                     547.51(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2740
_cell_measurement_theta_min      7.345
_cell_measurement_theta_max      54.915

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.772
_exptl_crystal_F_000             300
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.190
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.161
_shelx_estimated_absorpt_T_min   0.970
_shelx_estimated_absorpt_T_max   0.984
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6713
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4050
_diffrn_reflns_av_unetI/netI     0.0190
_diffrn_reflns_av_R_equivalents  0.0222
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_theta_min         3.673
_diffrn_reflns_theta_max         25.991
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measured_fraction_theta_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_point_group_measured_fraction_full 0.986
_reflns_number_total             1058
_reflns_number_gt                978
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0437P)²+0.1955P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1058
_refine_ls_number_parameters     107
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0370
_refine_ls_R_factor_gt           0.0342
_refine_ls_wR_factor_ref         0.0904
_refine_ls_wR_factor_gt          0.0877
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_restrained_S_all      1.058
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.4076(3) 0.74349(6) 0.4321(2) 0.0499(4) Uani 1 1 d . . . . .
O2 O 0.1811(3) 0.71189(6) 0.6425(2) 0.0532(4) Uani 1 1 d . . . . .
N1 N 0.3539(3) 0.53563(7) 0.2070(2) 0.0324(3) Uani 1 1 d . . . . .
H1 H 0.273(4) 0.5006(12) 0.245(3) 0.052(5) Uiso 1 1 d . . . . .
N2 N 0.5879(3) 0.59798(7) 0.0394(2) 0.0346(3) Uani 1 1 d . . . . .
N3 N 0.5116(3) 0.64371(7) 0.1785(2) 0.0338(3) Uani 1 1 d . . . . .
H3 H 0.552(4) 0.6905(12) 0.188(3) 0.051(5) Uiso 1 1 d . . . . .
N4 N 0.2507(3) 0.62560(7) 0.4291(2) 0.0358(3) Uani 1 1 d . . . . .
N5 N 0.2844(3) 0.69643(7) 0.4995(2) 0.0365(3) Uani 1 1 d . . . . .
C1 C 0.3689(3) 0.60693(8) 0.2808(2) 0.0304(3) Uani 1 1 d . . . . .
C2 C 0.4879(3) 0.53335(8) 0.0609(2) 0.0307(3) Uani 1 1 d . . . . .
O3 O 0.1020(3) 0.41223(10) 0.2760(3) 0.0683(5) Uani 1 1 d . . . . .
H3A H 0.017(10) 0.411(3) 0.361(8) 0.156(18) Uiso 1 1 d . . . . .
H3B H 0.092(17) 0.368(5) 0.245(14) 0.33(5) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 N5 1.2317(17) . ?
O2 N5 1.2477(16) . ?
N1 C1 1.3496(18) . ?
N1 C2 1.3571(19) . ?
N1 H1 0.84(2) . ?
N2 C2 1.2975(18) . ?
N2 N3 1.3666(17) . ?
N3 C1 1.3334(18) . ?
N3 H3 0.86(2) . ?
N4 N5 1.3319(17) . ?
N4 C1 1.3468(19) . ?
C2 C2 1.450(3) 3_665 ?
O3 H3A 0.82(5) . ?
O3 H3B 0.81(9) . ?

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
C1 N1 C2 106.61(12) . . ?
C1 N1 H1 125.1(14) . . ?
C2 N1 H1 128.3(14) . . ?
C2 N2 N3 103.73(12) . . ?
C1 N3 N2 111.82(12) . . ?
C1 N3 H3 128.3(13) . . ?
N2 N3 H3 119.9(13) . . ?
N5 N4 C1 115.47(12) . . ?
O1 N5 O2 121.89(13) . . ?
O1 N5 N4 123.71(12) . . ?
O2 N5 N4 114.41(12) . . ?
N3 C1 N4 134.93(13) . . ?
N3 C1 N1 105.59(12) . . ?
N4 C1 N1 119.48(13) . . ?
N2 C2 N1 112.25(12) . . ?
N2 C2 C2 123.87(17) . 3_665 ?
N1 C2 C2 123.87(16) . 3_665 ?
H3A O3 H3B 97(5) . . ?

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
C2 N2 N3 C1 0.00(16) . . . . ?
C1 N4 N5 O1 1.9(2) . . . . ?
C1 N4 N5 O2 -177.75(13) . . . . ?
N2 N3 C1 N4 179.96(15) . . . . ?
N2 N3 C1 N1 0.34(16) . . . . ?
N5 N4 C1 N3 -2.0(2) . . . . ?
N5 N4 C1 N1 177.57(13) . . . . ?
C2 N1 C1 N3 -0.53(16) . . . . ?
C2 N1 C1 N4 179.78(13) . . . . ?
N3 N2 C2 N1 -0.35(16) . . . . ?
N3 N2 C2 C2 178.53(17) . . . 3_665 ?
C1 N1 C2 N2 0.57(17) . . . . ?
C1 N1 C2 C2 -178.31(17) . . . 3_665 ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O3 H3B O2 0.81(9) 2.32(8) 2.8249(18) 121(6) 3_566 yes
O3 H3B O1 0.81(9) 2.49(9) 3.284(2) 166(7) 2_545 yes
O3 H3A N4 0.82(5) 2.36(5) 3.158(2) 165(4) 3_566 yes
O3 H3B O2 0.81(9) 2.32(8) 2.8249(18) 121(6) 3_566 yes
N3 H3 O2 0.86(2) 1.93(2) 2.7689(17) 164.1(19) 4_675 yes
N1 H1 O3 0.84(2) 1.87(2) 2.6917(19) 168(2) . yes

_refine_diff_density_max         0.282
_refine_diff_density_min         -0.170
_refine_diff_density_rms         0.036

####################################################################### 
# 
# 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_d8v18367_0m
_database_code_depnum_ccdc_archive 'CCDC 1917977'
loop_
_audit_author_name
_audit_author_address
'DONG CHEN'
;China Academy of Engineering Physics
China
;
_audit_update_record             
;
2019-05-23 deposited with the CCDC.	2019-12-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            H2BNT.2DMSO
_chemical_melting_point          ?
_chemical_formula_moiety         'C4 H4 N10 O4, 2(C2 H6 O S)'
_chemical_formula_sum            'C8 H16 N10 O6 S2'
_chemical_formula_weight         412.43

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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;

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

_cell_length_a                   12.9910(7)
_cell_length_b                   4.6699(2)
_cell_length_c                   14.4974(7)
_cell_angle_alpha                90
_cell_angle_beta                 95.171(2)
_cell_angle_gamma                90
_cell_volume                     875.93(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    7233
_cell_measurement_theta_min      4.413
_cell_measurement_theta_max      54.926

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.564
_exptl_crystal_F_000             428
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.170
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    0.356
_shelx_estimated_absorpt_T_min   0.942
_shelx_estimated_absorpt_T_max   0.982
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6139
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14378
_diffrn_reflns_av_unetI/netI     0.0296
_diffrn_reflns_av_R_equivalents  0.0567
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.822
_diffrn_reflns_theta_max         25.981
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             1709
_reflns_number_gt                1515
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 ? 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0669P)²+0.5123P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1709
_refine_ls_number_parameters     124
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0482
_refine_ls_R_factor_gt           0.0431
_refine_ls_wR_factor_ref         0.1267
_refine_ls_wR_factor_gt          0.1215
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_restrained_S_all      1.047
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.22265(5) 0.65160(13) 0.39207(4) 0.0494(2) Uani 1 1 d . . . . .
O1 O 0.59417(18) 0.3650(6) 0.14026(15) 0.0901(8) Uani 1 1 d . . . . .
O2 O 0.69206(14) 0.6775(4) 0.21440(12) 0.0610(5) Uani 1 1 d . . . . .
O3 O 0.31854(13) 0.4667(4) 0.39013(13) 0.0605(5) Uani 1 1 d . . . . .
N1 N 0.49124(13) 0.7462(4) 0.40121(11) 0.0383(4) Uani 1 1 d . . . . .
N2 N 0.63439(13) 0.9122(4) 0.36221(11) 0.0409(4) Uani 1 1 d . . . . .
H2 H 0.6883 0.9379 0.3329 0.049 Uiso 1 1 calc R U . . .
N3 N 0.61421(13) 1.0625(4) 0.43998(12) 0.0420(4) Uani 1 1 d . . . . .
N4 N 0.54238(14) 0.5345(5) 0.26798(12) 0.0491(5) Uani 1 1 d . . . . .
N5 N 0.61234(16) 0.5292(5) 0.20635(13) 0.0538(5) Uani 1 1 d . . . . .
C1 C 0.52672(15) 0.9538(5) 0.46078(13) 0.0359(4) Uani 1 1 d . . . . .
C2 C 0.56106(15) 0.7232(5) 0.33762(13) 0.0371(5) Uani 1 1 d . . . . .
C3 C 0.1367(2) 0.5174(8) 0.3007(2) 0.0752(9) Uani 1 1 d . . . . .
H3A H 0.1619 0.5658 0.2424 0.113 Uiso 1 1 calc R U . . .
H3B H 0.0695 0.6006 0.3041 0.113 Uiso 1 1 calc R U . . .
H3C H 0.1320 0.3130 0.3059 0.113 Uiso 1 1 calc R U . . .
C4 C 0.1601(3) 0.5263(9) 0.4869(2) 0.0825(10) Uani 1 1 d . . . . .
H4A H 0.1461 0.3254 0.4795 0.124 Uiso 1 1 calc R U . . .
H4B H 0.0962 0.6280 0.4899 0.124 Uiso 1 1 calc R U . . .
H4C H 0.2037 0.5573 0.5431 0.124 Uiso 1 1 calc R U . . .
H1 H 0.437(3) 0.656(7) 0.396(2) 0.083(11) 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
S1 O3 1.518(2) . ?
S1 C4 1.759(3) . ?
S1 C3 1.769(3) . ?
O1 N5 1.233(3) . ?
O2 N5 1.243(3) . ?
N1 C1 1.351(3) . ?
N1 C2 1.355(2) . ?
N1 H1 0.82(3) . ?
N2 C2 1.324(3) . ?
N2 N3 1.373(2) . ?
N2 H2 0.8600 . ?
N3 C1 1.305(3) . ?
N4 N5 1.331(2) . ?
N4 C2 1.346(3) . ?
C1 C1 1.450(4) 3_676 ?
C3 H3A 0.9600 . ?
C3 H3B 0.9600 . ?
C3 H3C 0.9600 . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?

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 S1 C4 105.25(15) . . ?
O3 S1 C3 104.39(14) . . ?
C4 S1 C3 99.35(16) . . ?
C1 N1 C2 106.34(18) . . ?
C1 N1 H1 132(2) . . ?
C2 N1 H1 122(2) . . ?
C2 N2 N3 112.09(15) . . ?
C2 N2 H2 124.0 . . ?
N3 N2 H2 124.0 . . ?
C1 N3 N2 103.03(17) . . ?
N5 N4 C2 115.33(19) . . ?
O1 N5 O2 121.27(19) . . ?
O1 N5 N4 116.0(2) . . ?
O2 N5 N4 122.72(19) . . ?
N3 C1 N1 112.67(17) . . ?
N3 C1 C1 123.6(2) . 3_676 ?
N1 C1 C1 123.7(2) . 3_676 ?
N2 C2 N4 135.69(17) . . ?
N2 C2 N1 105.87(18) . . ?
N4 C2 N1 118.43(19) . . ?
S1 C3 H3A 109.5 . . ?
S1 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
S1 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
S1 C4 H4A 109.5 . . ?
S1 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
S1 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?

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
C2 N2 N3 C1 0.5(2) . . . . ?
C2 N4 N5 O1 -177.4(2) . . . . ?
C2 N4 N5 O2 3.3(3) . . . . ?
N2 N3 C1 N1 0.0(2) . . . . ?
N2 N3 C1 C1 -179.9(3) . . . 3_676 ?
C2 N1 C1 N3 -0.4(3) . . . . ?
C2 N1 C1 C1 179.4(3) . . . 3_676 ?
N3 N2 C2 N4 177.8(2) . . . . ?
N3 N2 C2 N1 -0.7(2) . . . . ?
N5 N4 C2 N2 -0.5(4) . . . . ?
N5 N4 C2 N1 177.9(2) . . . . ?
C1 N1 C2 N2 0.7(2) . . . . ?
C1 N1 C2 N4 -178.15(19) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H2 O2 0.86 2.11 2.578(2) 113.7 .
N2 H2 O2 0.86 2.08 2.881(2) 154.7 2_655
C3 H3B O1 0.96 2.65 3.581(4) 164.3 2
C3 H3B N4 0.96 2.65 3.437(4) 139.2 2
N1 H1 S1 0.82(3) 2.78(3) 3.5078(19) 149(3) .
N1 H1 O3 0.82(3) 1.77(3) 2.588(2) 178(3) .
N2 H2 O2 0.86 2.11 2.578(2) 113.7 .
N2 H2 O2 0.86 2.08 2.881(2) 154.7 2_655
C3 H3B O1 0.96 2.65 3.581(4) 164.3 2
C3 H3B N4 0.96 2.65 3.437(4) 139.2 2

_refine_diff_density_max         0.525
_refine_diff_density_min         -0.341
_refine_diff_density_rms         0.051

_shelxl_version_number           2013-4


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: DMSO'
