# 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_LY181222_a
_database_code_depnum_ccdc_archive 'CCDC 1887194'
loop_
_audit_author_name
_audit_author_address
'yang liu'
;Nanjing University of Science & Technology
China
;
_audit_update_record             
;
2018-12-25 deposited with the CCDC.	2019-09-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C4 H4 N10 O5'
_chemical_formula_sum            'C4 H4 N10 O5'
_chemical_formula_weight         272.17

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

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

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

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

_cell_length_a                   10.0899(7)
_cell_length_b                   7.7440(5)
_cell_length_c                   13.7323(9)
_cell_angle_alpha                90
_cell_angle_beta                 110.922(2)
_cell_angle_gamma                90
_cell_volume                     1002.24(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    6294
_cell_measurement_theta_min      3.07
_cell_measurement_theta_max      27.50

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.804
_exptl_crystal_F_000             552
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    0.162
_shelx_estimated_absorpt_T_min   0.965
_shelx_estimated_absorpt_T_max   0.971
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6977
_exptl_absorpt_correction_T_max  0.7456
_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            10083
_diffrn_reflns_av_unetI/netI     0.0208
_diffrn_reflns_av_R_equivalents  0.0245
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.073
_diffrn_reflns_theta_max         27.535
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 0.991
_reflns_number_total             2280
_reflns_number_gt                1967
_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    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.0466P)²+0.4109P] 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     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.073(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2280
_refine_ls_number_parameters     176
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0430
_refine_ls_R_factor_gt           0.0367
_refine_ls_wR_factor_ref         0.0978
_refine_ls_wR_factor_gt          0.0942
_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
C1 C 0.17365(14) 0.65875(18) 0.63771(12) 0.0309(3) Uani 1 1 d . . . . .
C2 C 0.31374(14) 0.59382(17) 0.68953(11) 0.0254(3) Uani 1 1 d . . . . .
C3 C 0.43395(13) 0.61368(16) 0.65580(10) 0.0218(3) Uani 1 1 d . . . . .
C4 C 0.64905(14) 0.62151(17) 0.65238(10) 0.0253(3) Uani 1 1 d . . . . .
N1 N 0.31766(14) 0.51133(19) 0.77252(11) 0.0407(3) Uani 1 1 d . . . . .
N2 N 0.09424(14) 0.6152(2) 0.68997(13) 0.0480(4) Uani 1 1 d . . . . .
N3 N 0.13265(13) 0.75613(19) 0.54777(11) 0.0426(4) Uani 1 1 d . . . . .
H3 H 0.196226 0.814991 0.534170 0.051 Uiso 1 1 calc R U . . .
N4 N -0.00257(14) 0.76354(19) 0.47998(11) 0.0411(4) Uani 1 1 d . . . . .
N5 N 0.41925(12) 0.66847(15) 0.56340(9) 0.0275(3) Uani 1 1 d . . . . .
N6 N 0.57481(11) 0.58328(14) 0.71438(8) 0.0214(3) Uani 1 1 d . . . . .
N7 N 0.55463(13) 0.67265(15) 0.56247(9) 0.0281(3) Uani 1 1 d . . . . .
H7 H 0.571(2) 0.711(2) 0.5038(15) 0.042 Uiso 1 1 d . U . . .
N8 N 0.78752(14) 0.6037(2) 0.67932(11) 0.0415(4) Uani 1 1 d . . . . .
H8A H 0.827761 0.626869 0.635213 0.050 Uiso 1 1 calc R U . . .
H8B H 0.837587 0.568963 0.741011 0.050 Uiso 1 1 calc R U . . .
N9 N 0.63992(12) 0.49830(15) 0.80958(8) 0.0248(3) Uani 1 1 d . . . . .
N10 N 0.63665(12) 0.59641(15) 0.88729(8) 0.0245(3) Uani 1 1 d . . . . .
O1 O 0.18290(13) 0.52196(19) 0.77461(10) 0.0537(4) Uani 1 1 d . . . . .
O2 O -0.09231(12) 0.67337(19) 0.49534(12) 0.0577(4) Uani 1 1 d . . . . .
O3 O -0.02127(15) 0.8633(2) 0.40699(11) 0.0664(5) Uani 1 1 d . . . . .
O4 O 0.57455(12) 0.73991(13) 0.87436(8) 0.0327(3) Uani 1 1 d . . . . .
O5 O 0.69699(12) 0.53582(14) 0.97653(7) 0.0350(3) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N2 1.297(2) . ?
C1 N3 1.378(2) . ?
C1 C2 1.4278(19) . ?
C2 N1 1.2947(19) . ?
C2 C3 1.4529(18) . ?
C3 N5 1.2951(17) . ?
C3 N6 1.3806(16) . ?
C4 N8 1.3186(19) . ?
C4 N7 1.3224(19) . ?
C4 N6 1.3525(16) . ?
N1 O1 1.3727(17) . ?
N2 O1 1.3894(19) . ?
N3 N4 1.3507(17) . ?
N3 H3 0.8600 . ?
N4 O2 1.2200(19) . ?
N4 O3 1.225(2) . ?
N5 N7 1.3710(17) . ?
N6 N9 1.4001(15) . ?
N7 H7 0.93(2) . ?
N8 H8A 0.8600 . ?
N8 H8B 0.8600 . ?
N9 N10 1.3200(16) . ?
N10 O5 1.2488(14) . ?
N10 O4 1.2568(15) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 C1 N3 126.23(14) . . ?
N2 C1 C2 109.27(13) . . ?
N3 C1 C2 124.48(13) . . ?
N1 C2 C1 109.03(12) . . ?
N1 C2 C3 124.49(12) . . ?
C1 C2 C3 126.47(13) . . ?
N5 C3 N6 111.15(11) . . ?
N5 C3 C2 122.03(12) . . ?
N6 C3 C2 126.81(12) . . ?
N8 C4 N7 129.14(13) . . ?
N8 C4 N6 124.75(13) . . ?
N7 C4 N6 106.08(12) . . ?
C2 N1 O1 105.64(12) . . ?
C1 N2 O1 104.93(12) . . ?
N4 N3 C1 123.15(14) . . ?
N4 N3 H3 118.4 . . ?
C1 N3 H3 118.4 . . ?
O2 N4 O3 126.52(14) . . ?
O2 N4 N3 119.08(15) . . ?
O3 N4 N3 114.40(15) . . ?
C3 N5 N7 104.53(11) . . ?
C4 N6 C3 106.39(11) . . ?
C4 N6 N9 120.66(11) . . ?
C3 N6 N9 131.79(11) . . ?
C4 N7 N5 111.86(11) . . ?
C4 N7 H7 127.9(12) . . ?
N5 N7 H7 120.2(12) . . ?
C4 N8 H8A 120.0 . . ?
C4 N8 H8B 120.0 . . ?
H8A N8 H8B 120.0 . . ?
N10 N9 N6 110.21(10) . . ?
O5 N10 O4 120.97(11) . . ?
O5 N10 N9 115.65(11) . . ?
O4 N10 N9 123.36(11) . . ?
N1 O1 N2 111.12(11) . . ?

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
N2 C1 C2 N1 0.14(19) . . . . ?
N3 C1 C2 N1 178.55(15) . . . . ?
N2 C1 C2 C3 179.57(14) . . . . ?
N3 C1 C2 C3 -2.0(2) . . . . ?
N1 C2 C3 N5 166.85(14) . . . . ?
C1 C2 C3 N5 -12.5(2) . . . . ?
N1 C2 C3 N6 -14.8(2) . . . . ?
C1 C2 C3 N6 165.82(13) . . . . ?
C1 C2 N1 O1 0.12(17) . . . . ?
C3 C2 N1 O1 -179.32(13) . . . . ?
N3 C1 N2 O1 -178.70(15) . . . . ?
C2 C1 N2 O1 -0.33(18) . . . . ?
N2 C1 N3 N4 -26.9(3) . . . . ?
C2 C1 N3 N4 154.99(15) . . . . ?
C1 N3 N4 O2 -4.0(2) . . . . ?
C1 N3 N4 O3 176.44(16) . . . . ?
N6 C3 N5 N7 0.26(14) . . . . ?
C2 C3 N5 N7 178.81(12) . . . . ?
N8 C4 N6 C3 -177.75(14) . . . . ?
N7 C4 N6 C3 0.39(14) . . . . ?
N8 C4 N6 N9 -8.7(2) . . . . ?
N7 C4 N6 N9 169.48(11) . . . . ?
N5 C3 N6 C4 -0.42(15) . . . . ?
C2 C3 N6 C4 -178.88(13) . . . . ?
N5 C3 N6 N9 -167.81(12) . . . . ?
C2 C3 N6 N9 13.7(2) . . . . ?
N8 C4 N7 N5 177.78(14) . . . . ?
N6 C4 N7 N5 -0.25(15) . . . . ?
C3 N5 N7 C4 -0.01(15) . . . . ?
C4 N6 N9 N10 118.58(13) . . . . ?
C3 N6 N9 N10 -75.52(16) . . . . ?
N6 N9 N10 O5 -177.31(11) . . . . ?
N6 N9 N10 O4 4.43(17) . . . . ?
C2 N1 O1 N2 -0.34(19) . . . . ?
C1 N2 O1 N1 0.4(2) . . . . ?

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
N3 H3 N5 0.86 2.42 2.9027(18) 115.9 . yes
N3 H3 N9 0.86 2.61 3.0675(18) 114.3 2_656 yes
N3 H3 O5 0.86 2.05 2.8577(17) 155.2 2_656 yes
N7 H7 N10 0.93(2) 2.45(2) 3.3304(16) 159.6(16) 4_575 yes
N7 H7 O4 0.93(2) 1.83(2) 2.7463(15) 169.1(17) 4_575 yes
N7 H7 O5 0.93(2) 2.439(19) 3.1247(16) 130.9(15) 4_575 yes
N8 H8A N2 0.86 2.52 3.0469(19) 120.3 1_655 yes
N8 H8A O2 0.86 2.36 3.214(2) 171.5 1_655 yes
N8 H8B O3 0.86 2.28 3.0421(19) 148.4 4_676 yes

_refine_diff_density_max         0.255
_refine_diff_density_min         -0.257
_refine_diff_density_rms         0.041

####################################################################### 
# 
# 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_Ly190410_2_a
_database_code_depnum_ccdc_archive 'CCDC 1915061'
loop_
_audit_author_name
_audit_author_address
'yang liu'
;Nanjing University of Science and Technology
China
;
_audit_update_record             
;
2019-05-09 deposited with the CCDC.	2019-09-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C4 H4 N9 O3, H4 N'
_chemical_formula_sum            'C4 H8 N10 O3'
_chemical_formula_weight         244.20

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           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-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                   18.7451(9)
_cell_length_b                   7.3716(4)
_cell_length_c                   14.7077(6)
_cell_angle_alpha                90
_cell_angle_beta                 110.5010(10)
_cell_angle_gamma                90
_cell_volume                     1903.61(16)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    5148
_cell_measurement_theta_min      2.32
_cell_measurement_theta_max      27.42

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.704
_exptl_crystal_F_000             1008
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.280
_exptl_crystal_size_min          0.260
_exptl_absorpt_coefficient_mu    0.145
_shelx_estimated_absorpt_T_min   0.951
_shelx_estimated_absorpt_T_max   0.963
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6740
_exptl_absorpt_correction_T_max  0.7456
_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            9252
_diffrn_reflns_av_unetI/netI     0.0258
_diffrn_reflns_av_R_equivalents  0.0278
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.320
_diffrn_reflns_theta_max         27.498
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             2178
_reflns_number_gt                1782
_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-2014 (Sheldrick 2014)'
_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)+(0.0766P)²+2.2229P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2178
_refine_ls_number_parameters     154
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0597
_refine_ls_R_factor_gt           0.0479
_refine_ls_wR_factor_ref         0.1393
_refine_ls_wR_factor_gt          0.1314
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.038
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.60609(10) 0.8704(2) 0.51675(12) 0.0237(4) Uani 1 1 d . . . . .
C2 C 0.49934(9) 0.7494(2) 0.51379(12) 0.0212(4) Uani 1 1 d . . . . .
C3 C 0.43788(10) 0.6904(2) 0.54547(12) 0.0229(4) Uani 1 1 d . . . . .
C4 C 0.36707(9) 0.6021(2) 0.49062(12) 0.0233(4) Uani 1 1 d . . . . .
N1 N 0.56786(9) 0.8217(2) 0.42601(11) 0.0278(4) Uani 1 1 d . . . . .
N2 N 0.49975(8) 0.7454(2) 0.42513(10) 0.0259(4) Uani 1 1 d . . . . .
N3 N 0.56514(8) 0.8287(2) 0.57417(10) 0.0217(3) Uani 1 1 d . . . . .
N4 N 0.44008(9) 0.7188(2) 0.63337(11) 0.0343(4) Uani 1 1 d . . . . .
N5 N 0.32791(9) 0.5779(2) 0.54813(11) 0.0326(4) Uani 1 1 d . . . . .
N6 N 0.35213(8) 0.5522(2) 0.39602(10) 0.0273(4) Uani 1 1 d . . . . .
N7 N 0.28322(9) 0.4922(2) 0.34829(11) 0.0291(4) Uani 1 1 d . . . . .
N8 N 0.67458(9) 0.9489(3) 0.55275(12) 0.0398(5) Uani 1 1 d . . . . .
H8A H 0.699470 0.973868 0.515089 0.048 Uiso 1 1 calc R U . . .
H8B H 0.693748 0.974354 0.613582 0.048 Uiso 1 1 calc R U . . .
N9 N 0.59305(9) 0.8584(2) 0.67464(10) 0.0318(4) Uani 1 1 d . . . . .
H9A H 0.637570 0.904632 0.702115 0.038 Uiso 1 1 calc R U . . .
H9B H 0.565660 0.830460 0.708821 0.038 Uiso 1 1 calc R U . . .
N10 N 0.12075(9) 0.2336(2) 0.26600(11) 0.0315(4) Uani 1 1 d . . . . .
H10A H 0.082267 0.231264 0.206277 0.047 Uiso 1 1 d R U . . .
H10B H 0.157367 0.335964 0.266577 0.047 Uiso 1 1 d R U . . .
H10C H 0.101867 0.247864 0.318277 0.047 Uiso 1 1 d R U . . .
H10D H 0.151683 0.120386 0.274184 0.047 Uiso 1 1 d R U . . .
O1 O 0.37313(8) 0.6502(2) 0.63760(9) 0.0400(4) Uani 1 1 d . . . . .
O2 O 0.27154(8) 0.4389(2) 0.26218(10) 0.0394(4) Uani 1 1 d . . . . .
O3 O 0.23105(8) 0.4862(3) 0.38160(11) 0.0505(5) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.324(2) . ?
C1 N8 1.337(2) . ?
C1 N3 1.361(2) . ?
C2 N2 1.307(2) . ?
C2 N3 1.372(2) . ?
C2 C3 1.453(2) . ?
C3 N4 1.296(2) . ?
C3 C4 1.444(2) . ?
C4 N5 1.312(2) . ?
C4 N6 1.370(2) . ?
N1 N2 1.391(2) . ?
N3 N9 1.4014(19) . ?
N4 O1 1.375(2) . ?
N5 O1 1.397(2) . ?
N6 N7 1.312(2) . ?
N7 O3 1.238(2) . ?
N7 O2 1.270(2) . ?
N8 H8A 0.8600 . ?
N8 H8B 0.8600 . ?
N9 H9A 0.8600 . ?
N9 H9B 0.8600 . ?
N10 H10A 0.9212 . ?
N10 H10B 1.0182 . ?
N10 H10C 0.9582 . ?
N10 H10D 0.9990 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 N8 128.48(16) . . ?
N1 C1 N3 109.89(15) . . ?
N8 C1 N3 121.63(15) . . ?
N2 C2 N3 109.71(15) . . ?
N2 C2 C3 126.56(16) . . ?
N3 C2 C3 123.63(15) . . ?
N4 C3 C4 109.39(15) . . ?
N4 C3 C2 121.32(16) . . ?
C4 C3 C2 129.26(16) . . ?
N5 C4 N6 131.06(16) . . ?
N5 C4 C3 108.26(15) . . ?
N6 C4 C3 120.62(15) . . ?
C1 N1 N2 106.86(13) . . ?
C2 N2 N1 107.92(14) . . ?
C1 N3 C2 105.61(14) . . ?
C1 N3 N9 122.38(14) . . ?
C2 N3 N9 131.91(14) . . ?
C3 N4 O1 105.96(14) . . ?
C4 N5 O1 105.28(14) . . ?
N7 N6 C4 116.53(15) . . ?
O3 N7 O2 119.96(15) . . ?
O3 N7 N6 124.49(16) . . ?
O2 N7 N6 115.56(15) . . ?
C1 N8 H8A 120.0 . . ?
C1 N8 H8B 120.0 . . ?
H8A N8 H8B 120.0 . . ?
N3 N9 H9A 120.0 . . ?
N3 N9 H9B 120.0 . . ?
H9A N9 H9B 120.0 . . ?
H10A N10 H10B 108.8 . . ?
H10A N10 H10C 112.4 . . ?
H10B N10 H10C 110.4 . . ?
H10A N10 H10D 109.1 . . ?
H10B N10 H10D 104.9 . . ?
H10C N10 H10D 110.9 . . ?
N4 O1 N5 111.10(12) . . ?

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
N2 C2 C3 N4 -172.30(18) . . . . ?
N3 C2 C3 N4 3.8(3) . . . . ?
N2 C2 C3 C4 5.5(3) . . . . ?
N3 C2 C3 C4 -178.36(17) . . . . ?
N4 C3 C4 N5 -0.4(2) . . . . ?
C2 C3 C4 N5 -178.44(18) . . . . ?
N4 C3 C4 N6 -177.91(17) . . . . ?
C2 C3 C4 N6 4.1(3) . . . . ?
N8 C1 N1 N2 179.82(19) . . . . ?
N3 C1 N1 N2 -0.1(2) . . . . ?
N3 C2 N2 N1 0.8(2) . . . . ?
C3 C2 N2 N1 177.34(16) . . . . ?
C1 N1 N2 C2 -0.4(2) . . . . ?
N1 C1 N3 C2 0.5(2) . . . . ?
N8 C1 N3 C2 -179.39(17) . . . . ?
N1 C1 N3 N9 177.39(16) . . . . ?
N8 C1 N3 N9 -2.5(3) . . . . ?
N2 C2 N3 C1 -0.8(2) . . . . ?
C3 C2 N3 C1 -177.51(16) . . . . ?
N2 C2 N3 N9 -177.23(17) . . . . ?
C3 C2 N3 N9 6.1(3) . . . . ?
C4 C3 N4 O1 0.5(2) . . . . ?
C2 C3 N4 O1 178.71(16) . . . . ?
N6 C4 N5 O1 177.27(19) . . . . ?
C3 C4 N5 O1 0.1(2) . . . . ?
N5 C4 N6 N7 10.9(3) . . . . ?
C3 C4 N6 N7 -172.31(16) . . . . ?
C4 N6 N7 O3 3.5(3) . . . . ?
C4 N6 N7 O2 -176.89(16) . . . . ?
C3 N4 O1 N5 -0.4(2) . . . . ?
C4 N5 O1 N4 0.2(2) . . . . ?

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
N8 H8A N5 0.86 2.41 3.051(2) 131.9 3 yes
N8 H8A O3 0.86 2.24 3.066(2) 160.4 3 yes
N8 H8B O2 0.86 2.25 3.091(2) 164.5 8_566 yes
N9 H9A O2 0.86 2.62 3.474(2) 172.2 8_566 yes
N9 H9B N4 0.86 2.37 2.904(2) 120.5 . yes
N9 H9B N4 0.86 2.50 3.263(2) 148.2 2_656 yes
N9 H9B O1 0.86 2.52 3.026(2) 118.2 2_656 yes
N10 H10A N2 0.92 2.01 2.927(2) 175.8 4_545 yes
N10 H10B N7 1.02 2.52 3.434(2) 149.1 . yes
N10 H10B N9 1.02 2.69 3.261(2) 115.8 8_465 yes
N10 H10B O2 1.02 2.29 3.224(2) 151.4 . yes
N10 H10B O3 1.02 2.09 2.859(2) 130.7 . yes
N10 H10C N1 0.96 1.98 2.929(2) 170.1 3_445 yes
N10 H10D N7 1.00 2.68 3.369(2) 126.6 4_545 yes
N10 H10D O1 1.00 2.51 3.148(2) 121.4 7_556 yes
N10 H10D O2 1.00 2.16 3.091(2) 153.4 4_545 yes

_refine_diff_density_max         0.531
_refine_diff_density_min         -0.710
_refine_diff_density_rms         0.059

####################################################################### 
# 
# 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_Ly190505_1_a
_database_code_depnum_ccdc_archive 'CCDC 1915062'
loop_
_audit_author_name
_audit_author_address
'yang liu'
;Nanjing University of Science and Technology
China
;
_audit_update_record             
;
2019-05-09 deposited with the CCDC.	2019-09-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C4 H4 N9 O3, H5 N2, H2 O'
_chemical_formula_sum            'C4 H11 N11 O4'
_chemical_formula_weight         277.24

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

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

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

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

_cell_length_a                   9.0312(4)
_cell_length_b                   18.6286(7)
_cell_length_c                   6.5567(3)
_cell_angle_alpha                90
_cell_angle_beta                 96.737(2)
_cell_angle_gamma                90
_cell_volume                     1095.47(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    5027
_cell_measurement_theta_min      2.27
_cell_measurement_theta_max      27.41

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.681
_exptl_crystal_F_000             576
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    0.145
_shelx_estimated_absorpt_T_min   0.965
_shelx_estimated_absorpt_T_max   0.997
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6771
_exptl_absorpt_correction_T_max  0.7456
_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            9664
_diffrn_reflns_av_unetI/netI     0.0267
_diffrn_reflns_av_R_equivalents  0.0256
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         2.187
_diffrn_reflns_theta_max         27.488
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             2509
_reflns_number_gt                2045
_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-2014 (Sheldrick 2014)'
_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)+(0.0736P)²+0.6535P] 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         2509
_refine_ls_number_parameters     179
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0634
_refine_ls_R_factor_gt           0.0495
_refine_ls_wR_factor_ref         0.1411
_refine_ls_wR_factor_gt          0.1327
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_restrained_S_all      1.062
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.3808(2) 0.73776(9) 0.3155(3) 0.0221(4) Uani 1 1 d . . . . .
C2 C 0.46846(19) 0.62940(9) 0.3061(3) 0.0218(4) Uani 1 1 d . . . . .
C3 C 0.47727(19) 0.55240(9) 0.2745(3) 0.0222(4) Uani 1 1 d . . . . .
C4 C 0.6086(2) 0.50997(9) 0.2522(3) 0.0226(4) Uani 1 1 d . . . . .
N1 N 0.33868(16) 0.66872(8) 0.2768(2) 0.0219(3) Uani 1 1 d . . . . .
N2 N 0.52581(17) 0.74104(8) 0.3711(2) 0.0253(4) Uani 1 1 d . . . . .
N3 N 0.58074(17) 0.67154(8) 0.3647(2) 0.0256(4) Uani 1 1 d . . . . .
N4 N 0.36091(18) 0.51111(9) 0.2622(3) 0.0293(4) Uani 1 1 d . . . . .
N5 N 0.56716(18) 0.44269(8) 0.2256(3) 0.0284(4) Uani 1 1 d . . . . .
N6 N 0.19067(17) 0.64706(9) 0.2201(3) 0.0338(4) Uani 1 1 d . . . . .
H6A H 0.120255 0.678398 0.208077 0.041 Uiso 1 1 calc R U . . .
H6B H 0.170414 0.602458 0.197392 0.041 Uiso 1 1 calc R U . . .
N7 N 0.28443(19) 0.79323(9) 0.3003(3) 0.0314(4) Uani 1 1 d . . . . .
H7A H 0.316095 0.836052 0.328286 0.038 Uiso 1 1 calc R U . . .
H7B H 0.191254 0.785814 0.262541 0.038 Uiso 1 1 calc R U . . .
N8 N 0.74551(17) 0.54253(8) 0.2599(3) 0.0288(4) Uani 1 1 d . . . . .
N9 N 0.86171(18) 0.49938(9) 0.2595(3) 0.0364(5) Uani 1 1 d . . . . .
N10 N 0.9649(2) 0.80625(10) 0.0632(3) 0.0409(5) Uani 1 1 d . . . . .
H10A H 0.988320 0.818600 -0.049534 0.061 Uiso 1 1 d R U . . .
H10B H 0.904096 0.769234 0.048743 0.061 Uiso 1 1 d R U . . .
N11 N 0.86973(19) 0.86315(10) 0.1205(3) 0.0368(4) Uani 1 1 d . . . . .
H11A H 0.835653 0.852066 0.238502 0.055 Uiso 1 1 calc R U . . .
H11B H 0.793319 0.868654 0.022954 0.055 Uiso 1 1 calc R U . . .
H11C H 0.921485 0.903849 0.135310 0.055 Uiso 1 1 calc R U . . .
O1 O 0.41270(15) 0.44280(7) 0.2316(2) 0.0329(4) Uani 1 1 d . . . . .
O2 O 0.85097(18) 0.43311(8) 0.2473(3) 0.0551(5) Uani 1 1 d . . . . .
O3 O 0.98629(18) 0.52871(10) 0.2748(4) 0.0645(6) Uani 1 1 d . . . . .
O4 O 0.77775(17) 0.82306(8) 0.4932(3) 0.0351(4) Uani 1 1 d . . . . .
H4A H 0.768(3) 0.8552(17) 0.570(5) 0.053 Uiso 1 1 d . U . . .
H4B H 0.697(4) 0.8028(16) 0.461(5) 0.053 Uiso 1 1 d . U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N2 1.319(2) . ?
C1 N7 1.347(2) . ?
C1 N1 1.357(2) . ?
C2 N3 1.304(2) . ?
C2 N1 1.376(2) . ?
C2 C3 1.453(2) . ?
C3 N4 1.297(2) . ?
C3 C4 1.447(2) . ?
C4 N5 1.314(2) . ?
C4 N8 1.373(2) . ?
N1 N6 1.404(2) . ?
N2 N3 1.389(2) . ?
N4 O1 1.378(2) . ?
N5 O1 1.400(2) . ?
N6 H6A 0.8600 . ?
N6 H6B 0.8600 . ?
N7 H7A 0.8600 . ?
N7 H7B 0.8600 . ?
N8 N9 1.322(2) . ?
N9 O2 1.240(2) . ?
N9 O3 1.244(2) . ?
N10 N11 1.442(3) . ?
N10 H10A 0.8253 . ?
N10 H10B 0.8796 . ?
N11 H11A 0.8900 . ?
N11 H11B 0.8900 . ?
N11 H11C 0.8900 . ?
O4 H4A 0.79(3) . ?
O4 H4B 0.83(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
N2 C1 N7 126.64(17) . . ?
N2 C1 N1 110.06(15) . . ?
N7 C1 N1 123.29(17) . . ?
N3 C2 N1 109.93(16) . . ?
N3 C2 C3 125.63(16) . . ?
N1 C2 C3 124.44(16) . . ?
N4 C3 C4 109.72(16) . . ?
N4 C3 C2 122.47(16) . . ?
C4 C3 C2 127.81(16) . . ?
N5 C4 N8 131.89(17) . . ?
N5 C4 C3 108.08(16) . . ?
N8 C4 C3 120.02(16) . . ?
C1 N1 C2 105.24(14) . . ?
C1 N1 N6 124.00(15) . . ?
C2 N1 N6 130.75(15) . . ?
C1 N2 N3 107.16(14) . . ?
C2 N3 N2 107.57(15) . . ?
C3 N4 O1 105.68(14) . . ?
C4 N5 O1 105.31(14) . . ?
N1 N6 H6A 120.0 . . ?
N1 N6 H6B 120.0 . . ?
H6A N6 H6B 120.0 . . ?
C1 N7 H7A 120.0 . . ?
C1 N7 H7B 120.0 . . ?
H7A N7 H7B 120.0 . . ?
N9 N8 C4 116.29(16) . . ?
O2 N9 O3 120.36(17) . . ?
O2 N9 N8 123.31(17) . . ?
O3 N9 N8 116.32(17) . . ?
N11 N10 H10A 104.6 . . ?
N11 N10 H10B 102.8 . . ?
H10A N10 H10B 110.1 . . ?
N10 N11 H11A 109.5 . . ?
N10 N11 H11B 109.5 . . ?
H11A N11 H11B 109.5 . . ?
N10 N11 H11C 109.5 . . ?
H11A N11 H11C 109.5 . . ?
H11B N11 H11C 109.5 . . ?
N4 O1 N5 111.20(13) . . ?
H4A O4 H4B 110(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N3 C2 C3 N4 163.87(18) . . . . ?
N1 C2 C3 N4 -16.5(3) . . . . ?
N3 C2 C3 C4 -16.2(3) . . . . ?
N1 C2 C3 C4 163.46(18) . . . . ?
N4 C3 C4 N5 0.3(2) . . . . ?
C2 C3 C4 N5 -179.72(18) . . . . ?
N4 C3 C4 N8 179.90(17) . . . . ?
C2 C3 C4 N8 -0.1(3) . . . . ?
N2 C1 N1 C2 -1.8(2) . . . . ?
N7 C1 N1 C2 179.06(17) . . . . ?
N2 C1 N1 N6 178.06(16) . . . . ?
N7 C1 N1 N6 -1.1(3) . . . . ?
N3 C2 N1 C1 1.8(2) . . . . ?
C3 C2 N1 C1 -177.83(17) . . . . ?
N3 C2 N1 N6 -178.00(17) . . . . ?
C3 C2 N1 N6 2.3(3) . . . . ?
N7 C1 N2 N3 -179.78(18) . . . . ?
N1 C1 N2 N3 1.1(2) . . . . ?
N1 C2 N3 N2 -1.2(2) . . . . ?
C3 C2 N3 N2 178.47(17) . . . . ?
C1 N2 N3 C2 0.1(2) . . . . ?
C4 C3 N4 O1 -0.2(2) . . . . ?
C2 C3 N4 O1 179.74(16) . . . . ?
N8 C4 N5 O1 -179.74(19) . . . . ?
C3 C4 N5 O1 -0.2(2) . . . . ?
N5 C4 N8 N9 -7.2(3) . . . . ?
C3 C4 N8 N9 173.28(17) . . . . ?
C4 N8 N9 O2 2.0(3) . . . . ?
C4 N8 N9 O3 -177.2(2) . . . . ?
C3 N4 O1 N5 0.1(2) . . . . ?
C4 N5 O1 N4 0.0(2) . . . . ?

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
O4 H4B N2 0.83(3) 1.96(3) 2.779(2) 170(3) . yes
O4 H4A N8 0.79(3) 2.30(3) 3.087(2) 173(3) 4_576 yes
N11 H11C O3 0.89 2.52 3.386(3) 165.4 2_755 yes
N11 H11C O2 0.89 2.18 2.881(2) 135.5 2_755 yes
N11 H11C N9 0.89 2.68 3.535(2) 162.5 2_755 yes
N11 H11B N8 0.89 2.39 3.052(2) 131.1 4_575 yes
N11 H11B N3 0.89 2.20 3.002(2) 149.1 4_575 yes
N11 H11A O4 0.89 1.89 2.774(3) 175.0 . yes
N10 H10B O4 0.88 2.07 2.948(2) 173.4 4_575 yes
N10 H10A N6 0.83 2.58 3.324(3) 150.0 4_675 yes
N7 H7B N10 0.86 2.32 3.123(3) 154.4 1_455 yes
N7 H7A O2 0.86 2.37 2.880(2) 118.4 2_655 yes
N7 H7A N5 0.86 2.30 3.103(2) 156.5 2_655 yes
N6 H6B O3 0.86 2.26 2.924(2) 134.1 1_455 yes
N6 H6B N4 0.86 2.42 2.959(2) 121.1 . yes

_refine_diff_density_max         0.494
_refine_diff_density_min         -0.646
_refine_diff_density_rms         0.057

####################################################################### 
# 
# 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_Wq181211_1_a
_database_code_depnum_ccdc_archive 'CCDC 1887195'
loop_
_audit_author_name
_audit_author_address
'yang liu'
;Nanjing University of Science & Technology
China
;
_audit_update_record             
;
2018-12-25 deposited with the CCDC.	2019-09-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C4 H2 N10 O5, 2(H4 N)'
_chemical_formula_sum            'C4 H10 N12 O5'
_chemical_formula_weight         306.24

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

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

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

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

_cell_length_a                   14.260(2)
_cell_length_b                   4.9236(7)
_cell_length_c                   17.854(2)
_cell_angle_alpha                90
_cell_angle_beta                 103.382(4)
_cell_angle_gamma                90
_cell_volume                     1219.5(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    5515
_cell_measurement_theta_min      2.94
_cell_measurement_theta_max      26.83

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.668
_exptl_crystal_F_000             632
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    0.148
_shelx_estimated_absorpt_T_min   0.968
_shelx_estimated_absorpt_T_max   0.974
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6468
_exptl_absorpt_correction_T_max  0.7456
_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            12535
_diffrn_reflns_av_unetI/netI     0.0431
_diffrn_reflns_av_R_equivalents  0.0457
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.345
_diffrn_reflns_theta_max         27.546
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             2807
_reflns_number_gt                2030
_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 APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.0611P)²+0.2700P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2807
_refine_ls_number_parameters     220
_refine_ls_number_restraints     16
_refine_ls_R_factor_all          0.0690
_refine_ls_R_factor_gt           0.0440
_refine_ls_wR_factor_ref         0.1201
_refine_ls_wR_factor_gt          0.1081
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_restrained_S_all      1.041
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.39573(11) 0.0482(3) 0.65785(9) 0.0284(4) Uani 1 1 d . . . . .
C2 C 0.27871(12) 0.3425(3) 0.64394(9) 0.0287(4) Uani 1 1 d . . . . .
C3 C 0.19680(12) 0.5114(3) 0.60802(9) 0.0295(4) Uani 1 1 d . . . . .
C4 C 0.14662(12) 0.7086(3) 0.64384(9) 0.0306(4) Uani 1 1 d . . . . .
N1 N 0.45800(12) -0.1313(3) 0.63986(9) 0.0401(4) Uani 1 1 d . . . . .
H1A H 0.4973(16) -0.221(5) 0.6811(13) 0.060 Uiso 1 1 d . U . . .
H1B H 0.4395(17) -0.233(5) 0.5936(14) 0.060 Uiso 1 1 d . U . . .
N2 N 0.39899(10) 0.1571(3) 0.72566(8) 0.0331(4) Uani 1 1 d . . . . .
N3 N 0.32385(11) 0.3463(3) 0.71612(8) 0.0342(4) Uani 1 1 d . . . . .
N4 N 0.32083(10) 0.1557(3) 0.60459(7) 0.0287(3) Uani 1 1 d . . . . .
N5 N 0.29852(10) 0.0892(3) 0.52637(7) 0.0302(3) Uani 1 1 d . . . . .
N6 N 0.34538(11) 0.2560(3) 0.49020(8) 0.0349(4) Uani 1 1 d . . . . .
N7 N 0.15906(11) 0.5034(3) 0.53465(8) 0.0393(4) Uani 1 1 d . . . . .
N8 N 0.07843(11) 0.8182(3) 0.58989(8) 0.0394(4) Uani 1 1 d . . . . .
N9 N 0.17202(11) 0.7539(3) 0.72194(8) 0.0369(4) Uani 1 1 d . . . . .
N10 N 0.12565(11) 0.9490(3) 0.74859(9) 0.0370(4) Uani 1 1 d . . . . .
N11 N 0.11947(12) 0.4652(3) 0.89351(9) 0.0363(4) Uani 1 1 d D . . . .
H11C H 0.1278(15) 0.610(3) 0.8689(12) 0.054 Uiso 1 1 d D U . . .
H11D H 0.1274(16) 0.322(3) 0.8663(10) 0.054 Uiso 1 1 d D U . . .
H11B H 0.0629(10) 0.456(4) 0.9020(11) 0.054 Uiso 1 1 d D U . . .
H11A H 0.1620(12) 0.448(4) 0.9389(9) 0.054 Uiso 1 1 d D U . . .
N12 N 0.35570(13) 0.7296(4) 0.34466(10) 0.0456(4) Uani 1 1 d D . . . .
H12A H 0.3319(16) 0.607(4) 0.3694(11) 0.068 Uiso 1 1 d D U . . .
H12D H 0.3142(15) 0.788(4) 0.3065(9) 0.068 Uiso 1 1 d D U . . .
H12C H 0.3797(15) 0.838(4) 0.3784(10) 0.068 Uiso 1 1 d D U . . .
H12B H 0.3924(15) 0.657(4) 0.3189(11) 0.068 Uiso 1 1 d D U . . .
O1 O 0.39981(13) 0.4380(3) 0.52178(9) 0.0686(5) Uani 1 1 d . . . . .
O2 O 0.32988(11) 0.2189(3) 0.41839(7) 0.0471(4) Uani 1 1 d . . . . .
O3 O 0.06552(10) 1.1005(3) 0.70918(8) 0.0534(4) Uani 1 1 d . . . . .
O4 O 0.14927(10) 0.9748(3) 0.82194(7) 0.0452(4) Uani 1 1 d . . . . .
O5 O 0.08550(9) 0.6905(3) 0.52181(7) 0.0433(4) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N2 1.315(2) . ?
C1 N1 1.343(2) . ?
C1 N4 1.362(2) . ?
C2 N3 1.301(2) . ?
C2 N4 1.377(2) . ?
C2 C3 1.456(2) . ?
C3 N7 1.297(2) . ?
C3 C4 1.441(2) . ?
C4 N8 1.316(2) . ?
C4 N9 1.375(2) . ?
N1 H1A 0.93(2) . ?
N1 H1B 0.95(2) . ?
N2 N3 1.400(2) . ?
N4 N5 1.3974(17) . ?
N5 N6 1.318(2) . ?
N6 O1 1.233(2) . ?
N6 O2 1.2629(18) . ?
N7 O5 1.3745(19) . ?
N8 O5 1.3930(19) . ?
N9 N10 1.316(2) . ?
N10 O3 1.228(2) . ?
N10 O4 1.2808(19) . ?
N11 H11C 0.862(14) . ?
N11 H11D 0.878(14) . ?
N11 H11B 0.856(14) . ?
N11 H11A 0.897(13) . ?
N12 H12A 0.864(14) . ?
N12 H12D 0.843(14) . ?
N12 H12C 0.817(14) . ?
N12 H12B 0.850(14) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 C1 N1 127.14(15) . . ?
N2 C1 N4 109.83(14) . . ?
N1 C1 N4 122.93(15) . . ?
N3 C2 N4 109.93(14) . . ?
N3 C2 C3 126.22(15) . . ?
N4 C2 C3 123.84(14) . . ?
N7 C3 C4 109.64(15) . . ?
N7 C3 C2 122.07(15) . . ?
C4 C3 C2 128.28(15) . . ?
N8 C4 N9 130.71(16) . . ?
N8 C4 C3 108.08(14) . . ?
N9 C4 C3 121.21(15) . . ?
C1 N1 H1A 115.8(13) . . ?
C1 N1 H1B 119.3(14) . . ?
H1A N1 H1B 116(2) . . ?
C1 N2 N3 107.24(13) . . ?
C2 N3 N2 107.47(13) . . ?
C1 N4 C2 105.52(13) . . ?
C1 N4 N5 124.55(13) . . ?
C2 N4 N5 129.87(13) . . ?
N6 N5 N4 108.64(13) . . ?
O1 N6 O2 120.87(15) . . ?
O1 N6 N5 124.43(14) . . ?
O2 N6 N5 114.70(14) . . ?
C3 N7 O5 105.71(13) . . ?
C4 N8 O5 105.26(14) . . ?
N10 N9 C4 116.65(15) . . ?
O3 N10 O4 120.63(15) . . ?
O3 N10 N9 125.37(16) . . ?
O4 N10 N9 113.99(15) . . ?
H11C N11 H11D 109.4(16) . . ?
H11C N11 H11B 112.5(17) . . ?
H11D N11 H11B 107(2) . . ?
H11C N11 H11A 113(2) . . ?
H11D N11 H11A 106.3(17) . . ?
H11B N11 H11A 107.7(16) . . ?
H12A N12 H12D 111.6(19) . . ?
H12A N12 H12C 103(2) . . ?
H12D N12 H12C 118(2) . . ?
H12A N12 H12B 110.3(19) . . ?
H12D N12 H12B 96(2) . . ?
H12C N12 H12B 118(2) . . ?
N7 O5 N8 111.31(12) . . ?

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
N3 C2 C3 N7 176.56(17) . . . . ?
N4 C2 C3 N7 -2.3(3) . . . . ?
N3 C2 C3 C4 -2.3(3) . . . . ?
N4 C2 C3 C4 178.91(15) . . . . ?
N7 C3 C4 N8 -0.2(2) . . . . ?
C2 C3 C4 N8 178.70(16) . . . . ?
N7 C3 C4 N9 179.19(15) . . . . ?
C2 C3 C4 N9 -1.9(3) . . . . ?
N1 C1 N2 N3 175.79(17) . . . . ?
N4 C1 N2 N3 -0.79(19) . . . . ?
N4 C2 N3 N2 0.28(18) . . . . ?
C3 C2 N3 N2 -178.69(16) . . . . ?
C1 N2 N3 C2 0.31(18) . . . . ?
N2 C1 N4 C2 0.94(19) . . . . ?
N1 C1 N4 C2 -175.81(16) . . . . ?
N2 C1 N4 N5 178.30(14) . . . . ?
N1 C1 N4 N5 1.5(3) . . . . ?
N3 C2 N4 C1 -0.74(19) . . . . ?
C3 C2 N4 C1 178.26(15) . . . . ?
N3 C2 N4 N5 -177.91(15) . . . . ?
C3 C2 N4 N5 1.1(3) . . . . ?
C1 N4 N5 N6 -89.89(18) . . . . ?
C2 N4 N5 N6 86.79(19) . . . . ?
N4 N5 N6 O1 0.3(2) . . . . ?
N4 N5 N6 O2 -178.96(13) . . . . ?
C4 C3 N7 O5 -0.04(19) . . . . ?
C2 C3 N7 O5 -179.06(15) . . . . ?
N9 C4 N8 O5 -178.95(17) . . . . ?
C3 C4 N8 O5 0.39(19) . . . . ?
N8 C4 N9 N10 -4.5(3) . . . . ?
C3 C4 N9 N10 176.18(15) . . . . ?
C4 N9 N10 O3 -3.7(3) . . . . ?
C4 N9 N10 O4 177.21(14) . . . . ?
C3 N7 O5 N8 0.30(18) . . . . ?
C4 N8 O5 N7 -0.44(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
_geom_hbond_publ_flag
N1 H1A N2 0.93(2) 2.04(2) 2.957(2) 168(2) 2_646 yes
N1 H1B O1 0.95(2) 2.06(2) 2.970(2) 160(2) 1_545 yes
N11 H11C O4 0.862(14) 2.033(14) 2.891(2) 173.7(19) . yes
N11 H11D O4 0.878(14) 1.940(14) 2.810(2) 170.7(18) 1_545 yes
N11 H11B N8 0.856(14) 2.162(14) 2.994(2) 164(2) 2_546 yes
N11 H11B O3 0.856(14) 2.473(18) 2.920(2) 113.3(15) 2_546 yes
N11 H11A N5 0.897(13) 2.203(14) 3.068(2) 161.8(17) 4_566 yes
N12 H12A O2 0.864(14) 2.103(17) 2.901(2) 153(2) . yes
N12 H12A O4 0.864(14) 2.58(2) 3.048(2) 115.3(17) 4_575 yes
N12 H12D N3 0.843(14) 2.442(19) 3.058(2) 130.6(19) 4_575 yes
N12 H12D N9 0.843(14) 2.241(17) 3.002(2) 150(2) 4_575 yes
N12 H12C O2 0.817(14) 2.184(19) 2.810(2) 134(2) 1_565 yes
N12 H12B N2 0.850(14) 2.292(17) 3.021(2) 144(2) 4_565 yes

_refine_diff_density_max         0.224
_refine_diff_density_min         -0.291
_refine_diff_density_rms         0.048

