# Electronic Supplementary Material (ESI) for Dalton Transactions.
# 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_32
_database_code_depnum_ccdc_archive 'CCDC 1840856'
loop_
_audit_author_name
_audit_author_address
'Zhang jinhao'
;SWUST
China
;
_audit_update_record             
;
2018-05-02 deposited with the CCDC.	2019-07-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H20 N20 O6'
_chemical_formula_weight         540.48

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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                   3.7719(4)
_cell_length_b                   10.4109(10)
_cell_length_c                   14.7027(19)
_cell_angle_alpha                105.675(10)
_cell_angle_beta                 95.669(9)
_cell_angle_gamma                98.072(8)
_cell_volume                     544.69(11)
_cell_formula_units_Z            1
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    1347
_cell_measurement_theta_min      4.7410
_cell_measurement_theta_max      73.2030

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.648
_exptl_crystal_F_000             280
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.190
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.170
_exptl_absorpt_coefficient_mu    1.171
_shelx_estimated_absorpt_T_min   0.808
_shelx_estimated_absorpt_T_max   0.826
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  bruker-CCD
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            2586
_diffrn_reflns_av_unetI/netI     0.0662
_diffrn_reflns_av_R_equivalents  0.0637
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         4.678
_diffrn_reflns_theta_max         65.986
_diffrn_reflns_theta_full        65.986
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measured_fraction_theta_full 0.973
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_Laue_measured_fraction_full 0.973
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_point_group_measured_fraction_full 0.973
_reflns_number_total             1862
_reflns_number_gt                1443
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0212P)²+7.4320P] 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         1862
_refine_ls_number_parameters     172
_refine_ls_number_restraints     114
_refine_ls_R_factor_all          0.1324
_refine_ls_R_factor_gt           0.1073
_refine_ls_wR_factor_ref         0.2572
_refine_ls_wR_factor_gt          0.2296
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_restrained_S_all      1.036
_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
O1W O -0.2631(13) 0.0806(5) 0.7396(3) 0.0301(12) Uani 1 1 d . U . . .
H1WA H -0.2341 -0.0069 0.7459 0.045 Uiso 1 1 d R U . . .
H1WB H -0.0687 0.1479 0.7794 0.045 Uiso 1 1 d R U . . .
O1 O 0.0585(13) -0.0257(4) 0.8433(3) 0.0321(12) Uani 1 1 d . U . . .
O2 O 0.1767(13) 0.2083(4) 0.6522(3) 0.0285(11) Uani 1 1 d . U . . .
H2WA H 0.2714 0.1436 0.6712 0.034 Uiso 1 1 d R U . . .
N1 N -0.4604(15) 0.4700(5) 0.7043(4) 0.0269(13) Uani 1 1 d . U . . .
H1 H -0.5707 0.3850 0.6846 0.032 Uiso 1 1 calc R U . . .
N2 N -0.1271(15) 0.6570(5) 0.7903(4) 0.0243(13) Uani 1 1 d . U . . .
H2 H 0.0210 0.7174 0.8372 0.029 Uiso 1 1 calc R U . . .
N3 N 0.2639(15) 0.0738(5) 0.9153(4) 0.0239(12) Uani 1 1 d . U . . .
N4 N 0.2722(16) 0.2042(5) 0.9200(4) 0.0289(14) Uani 1 1 d . U . . .
N5 N 0.4918(15) 0.2728(5) 0.9995(4) 0.0292(14) Uani 1 1 d . U . . .
N6 N 0.6201(15) 0.1884(5) 1.0435(4) 0.0282(13) Uani 1 1 d . U . . .
N7 N 0.0042(14) 0.1798(5) 0.5638(4) 0.0234(12) Uani 1 1 d . U . . .
N8 N -0.1410(16) 0.2723(5) 0.5325(4) 0.0281(13) Uani 1 1 d . U . . .
N9 N -0.2943(15) 0.2084(5) 0.4436(4) 0.0273(13) Uani 1 1 d . U . . .
N10 N -0.2483(14) 0.0786(5) 0.4187(4) 0.0245(12) Uani 1 1 d . U . . .
C1 C -0.143(2) 0.4615(7) 0.8608(5) 0.0347(18) Uani 1 1 d . U . . .
H1A H -0.2626 0.3664 0.8399 0.052 Uiso 1 1 calc R U . . .
H1B H 0.1201 0.4661 0.8708 0.052 Uiso 1 1 calc R U . . .
H1C H -0.2216 0.5080 0.9207 0.052 Uiso 1 1 calc R U . . .
C2 C -0.2389(18) 0.5274(6) 0.7872(5) 0.0280(15) Uani 1 1 d . U . . .
C3 C -0.2795(18) 0.6806(7) 0.7091(5) 0.0275(15) Uani 1 1 d . U . . .
H3 H -0.2437 0.7640 0.6937 0.033 Uiso 1 1 calc R U . . .
C4 C -0.4889(19) 0.5641(7) 0.6550(5) 0.0306(16) Uani 1 1 d . U . . .
H4 H -0.6290 0.5497 0.5947 0.037 Uiso 1 1 calc R U . . .
C5 C 0.4710(18) 0.0621(6) 0.9902(5) 0.0224(14) Uani 1 1 d . U . . .
C6 C -0.0583(16) 0.0607(6) 0.4946(5) 0.0212(13) Uani 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
O1W H1WA 0.9601 . ?
O1W H1WB 0.9600 . ?
O1 N3 1.347(7) . ?
O2 N7 1.331(7) . ?
O2 H2WA 0.8999 . ?
N1 C2 1.343(8) . ?
N1 C4 1.377(9) . ?
N1 H1 0.8800 . ?
N2 C2 1.342(8) . ?
N2 C3 1.371(9) . ?
N2 H2 0.8800 . ?
N3 C5 1.329(8) . ?
N3 N4 1.337(7) . ?
N4 N5 1.324(8) . ?
N5 N6 1.337(8) . ?
N6 C5 1.344(8) . ?
N7 N8 1.333(8) . ?
N7 C6 1.348(8) . ?
N8 N9 1.327(8) . ?
N9 N10 1.342(7) . ?
N10 C6 1.337(8) . ?
C1 C2 1.472(10) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C3 C4 1.346(9) . ?
C3 H3 0.9500 . ?
C4 H4 0.9500 . ?
C5 C5 1.439(12) 2_657 ?
C6 C6 1.438(12) 2_556 ?

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
H1WA O1W H1WB 109.5 . . ?
N7 O2 H2WA 119.6 . . ?
C2 N1 C4 109.7(6) . . ?
C2 N1 H1 125.1 . . ?
C4 N1 H1 125.1 . . ?
C2 N2 C3 109.5(5) . . ?
C2 N2 H2 125.3 . . ?
C3 N2 H2 125.3 . . ?
C5 N3 N4 110.5(5) . . ?
C5 N3 O1 128.2(5) . . ?
N4 N3 O1 121.3(5) . . ?
N5 N4 N3 105.2(5) . . ?
N4 N5 N6 110.7(5) . . ?
N5 N6 C5 106.6(5) . . ?
O2 N7 N8 121.8(5) . . ?
O2 N7 C6 128.1(5) . . ?
N8 N7 C6 110.0(5) . . ?
N9 N8 N7 105.3(5) . . ?
N8 N9 N10 111.1(5) . . ?
C6 N10 N9 106.3(5) . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
N2 C2 N1 106.6(6) . . ?
N2 C2 C1 126.8(6) . . ?
N1 C2 C1 126.6(6) . . ?
C4 C3 N2 107.6(6) . . ?
C4 C3 H3 126.2 . . ?
N2 C3 H3 126.2 . . ?
C3 C4 N1 106.6(6) . . ?
C3 C4 H4 126.7 . . ?
N1 C4 H4 126.7 . . ?
N3 C5 N6 106.9(5) . . ?
N3 C5 C5 126.5(7) . 2_657 ?
N6 C5 C5 126.6(7) . 2_657 ?
N10 C6 N7 107.3(5) . . ?
N10 C6 C6 128.5(7) . 2_556 ?
N7 C6 C6 124.2(7) . 2_556 ?

_refine_diff_density_max         0.660
_refine_diff_density_min         -0.769
_refine_diff_density_rms         0.168

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1
_database_code_depnum_ccdc_archive 'CCDC 1840941'
loop_
_audit_author_name
_audit_author_address
'Zhang jinhao'
;SWUST
China
;
_audit_update_record             
;
2018-05-02 deposited with the CCDC.	2019-07-02 downloaded from the CCDC.
;
_audit_creation_date             2018-04-28
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.04.26 svn.r3504 for OlexSys, GUI svn.r5492)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C2 H N8 O2, C2 H5 N4'
_chemical_formula_sum            'C4 H6 N12 O2'
_chemical_formula_weight         254.21
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   3.79910(10)
_cell_length_b                   12.3968(4)
_cell_length_c                   19.5608(6)
_cell_angle_alpha                90
_cell_angle_beta                 90.308(3)
_cell_angle_gamma                90
_cell_volume                     921.24(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1591
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      73.4550
_cell_measurement_theta_min      4.4940
_shelx_estimated_absorpt_T_max   0.806
_shelx_estimated_absorpt_T_min   0.787
_exptl_absorpt_coefficient_mu    1.323
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.58752
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.44a (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.833
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             520
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.17
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0307
_diffrn_reflns_av_unetI/netI     0.0383
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -3
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            2899
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        65.976
_diffrn_reflns_theta_max         65.976
_diffrn_reflns_theta_min         4.222
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.6525
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -61.00 -26.00   1.00    1.00    --  -41.14  38.00-180.00   35
  2  ω   -109.00 -18.00   1.00    1.00    --  -41.14 -57.00  30.00   91
  3  ω    128.00 155.00   1.00    1.00    --  106.40 125.00-120.00   27
  4  ω     24.00 103.00   1.00    1.00    --  106.40 -95.00-150.00   79
  5  ω     49.00 159.00   1.00    1.00    --  106.40 -15.00-180.00  110
  6  ω      1.00  69.00   1.00    1.00    --   41.33 -99.00-120.00   68
  7  ω     97.00 130.00   1.00    1.00    --  106.40 125.00-120.00   33
  8  ω     87.00 127.00   1.00    1.00    --  106.40 -61.00 150.00   40
  9  ω     34.00  68.00   1.00    1.00    --  106.40-125.00  90.00   34
 10  ω     79.00 105.00   1.00    1.00    --  106.40-125.00  90.00   26
 11  ω     36.00  62.00   1.00    1.00    --  106.40 -61.00 150.00   26
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0153491000
_diffrn_orient_matrix_UB_12      -0.1239410000
_diffrn_orient_matrix_UB_13      0.0048579000
_diffrn_orient_matrix_UB_21      0.0069451000
_diffrn_orient_matrix_UB_22      -0.0075909000
_diffrn_orient_matrix_UB_23      -0.0785900000
_diffrn_orient_matrix_UB_31      0.4051934000
_diffrn_orient_matrix_UB_32      0.0048030000
_diffrn_orient_matrix_UB_33      0.0015872000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1443
_reflns_number_total             1608
_reflns_odcompleteness_completeness 99.25
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.49
_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 1.171.39.44a (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.44a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.44a (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.277
_refine_diff_density_min         -0.290
_refine_diff_density_rms         0.072
_refine_ls_extinction_coef       0.0048(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         1608
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0487
_refine_ls_R_factor_gt           0.0451
_refine_ls_restrained_S_all      1.060
_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)+(0.0800P)²+0.1492P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1197
_refine_ls_wR_factor_ref         0.1258
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups, All N(H,H) groups
 At 1.5 times of:
  All O(H) groups
2.a Riding coordinates:
 O2(H2)
2.b Aromatic/amide H refined with riding coordinates:
 N9(H9), N11(H11), C3(H3)
2.c X=CH2 refined with riding coordinates:
 N12(H12A,H12B)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.7022(4) 0.79106(11) 0.73565(7) 0.0264(4) Uani 1 1 d . . . . .
O2 O 0.0353(3) 0.42808(11) 0.68905(7) 0.0219(4) Uani 1 1 d . . . . .
H2 H 0.1789 0.3789 0.7162 0.033 Uiso 1 1 d R . . . .
N1 N 0.5392(4) 0.71634(13) 0.77233(8) 0.0177(4) Uani 1 1 d . . . . .
N2 N 0.4793(4) 0.72783(14) 0.83894(8) 0.0226(4) Uani 1 1 d . . . . .
N3 N 0.3112(4) 0.64005(15) 0.85798(8) 0.0246(4) Uani 1 1 d . . . . .
N4 N 0.2617(4) 0.57268(14) 0.80482(8) 0.0231(4) Uani 1 1 d . . . . .
N5 N 0.2729(4) 0.49178(13) 0.65837(8) 0.0167(4) Uani 1 1 d . . . . .
N6 N 0.3545(4) 0.47863(13) 0.59280(8) 0.0208(4) Uani 1 1 d . . . . .
N7 N 0.5610(4) 0.55864(13) 0.57704(8) 0.0205(4) Uani 1 1 d . . . . .
N8 N 0.6134(4) 0.62378(13) 0.63198(8) 0.0175(4) Uani 1 1 d . . . . .
C1 C 0.4055(4) 0.62150(15) 0.75140(10) 0.0161(4) Uani 1 1 d . . . . .
C2 C 0.4294(4) 0.58123(15) 0.68269(9) 0.0151(4) Uani 1 1 d . . . . .
N9 N 1.0171(4) 0.80194(13) 0.59033(8) 0.0178(4) Uani 1 1 d . . . . .
H9 H 0.9086 0.7563 0.6158 0.021 Uiso 1 1 calc R . . . .
N10 N 1.3140(4) 0.94727(13) 0.56086(8) 0.0199(4) Uani 1 1 d . . . . .
N11 N 1.2484(4) 0.88154(13) 0.50516(8) 0.0194(4) Uani 1 1 d . . . . .
H11 H 1.3158 0.8955 0.4642 0.023 Uiso 1 1 calc R . . . .
N12 N 0.9603(5) 0.71539(14) 0.48171(9) 0.0272(4) Uani 1 1 d . . . . .
H12A H 1.0063 0.7180 0.4387 0.033 Uiso 1 1 calc R . . . .
H12B H 0.8445 0.6618 0.4981 0.033 Uiso 1 1 calc R . . . .
C3 C 1.1705(5) 0.89630(15) 0.61104(10) 0.0186(4) Uani 1 1 d . . . . .
H3 H 1.1713 0.9208 0.6560 0.022 Uiso 1 1 calc R . . . .
C4 C 1.0682(4) 0.79413(15) 0.52276(10) 0.0171(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
O1 N1 1.327(2) . ?
O2 H2 0.9733 . ?
O2 N5 1.343(2) . ?
N1 N2 1.332(2) . ?
N1 C1 1.344(2) . ?
N2 N3 1.317(2) . ?
N3 N4 1.346(2) . ?
N4 C1 1.328(2) . ?
N5 N6 1.331(2) . ?
N5 C2 1.344(2) . ?
N6 N7 1.303(2) . ?
N7 N8 1.358(2) . ?
N8 C2 1.326(2) . ?
C1 C2 1.437(3) . ?
N9 H9 0.8600 . ?
N9 C3 1.367(2) . ?
N9 C4 1.340(2) . ?
N10 N11 1.382(2) . ?
N10 C3 1.291(2) . ?
N11 H11 0.8600 . ?
N11 C4 1.328(2) . ?
N12 H12A 0.8600 . ?
N12 H12B 0.8600 . ?
N12 C4 1.327(2) . ?
C3 H3 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N5 O2 H2 103.6 . . ?
O1 N1 N2 122.48(15) . . ?
O1 N1 C1 128.52(16) . . ?
N2 N1 C1 108.99(16) . . ?
N3 N2 N1 105.91(15) . . ?
N2 N3 N4 111.12(15) . . ?
C1 N4 N3 105.58(16) . . ?
O2 N5 C2 128.60(16) . . ?
N6 N5 O2 121.27(15) . . ?
N6 N5 C2 109.71(15) . . ?
N7 N6 N5 106.17(15) . . ?
N6 N7 N8 110.58(15) . . ?
C2 N8 N7 106.24(15) . . ?
N1 C1 C2 124.28(17) . . ?
N4 C1 N1 108.40(17) . . ?
N4 C1 C2 127.29(18) . . ?
N5 C2 C1 125.99(17) . . ?
N8 C2 N5 107.31(16) . . ?
N8 C2 C1 126.69(17) . . ?
C3 N9 H9 126.6 . . ?
C4 N9 H9 126.6 . . ?
C4 N9 C3 106.87(16) . . ?
C3 N10 N11 103.63(15) . . ?
N10 N11 H11 124.2 . . ?
C4 N11 N10 111.57(15) . . ?
C4 N11 H11 124.2 . . ?
H12A N12 H12B 120.0 . . ?
C4 N12 H12A 120.0 . . ?
C4 N12 H12B 120.0 . . ?
N9 C3 H3 124.0 . . ?
N10 C3 N9 112.00(17) . . ?
N10 C3 H3 124.0 . . ?
N11 C4 N9 105.92(16) . . ?
N12 C4 N9 127.13(18) . . ?
N12 C4 N11 126.94(18) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.262
_oxdiff_exptl_absorpt_empirical_full_min 0.604
####################################################################### 
# 
# 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_5
_database_code_depnum_ccdc_archive 'CCDC 1850642'
loop_
_audit_author_name
_audit_author_address
'Zhang jinhao'
;SWUST
China
;
_audit_update_record             
;
2018-06-20 deposited with the CCDC.	2019-07-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10 H12 N20 O4'
_chemical_formula_weight         476.40

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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                   7.2291(7)
_cell_length_b                   9.8660(9)
_cell_length_c                   13.8595(12)
_cell_angle_alpha                89.590(7)
_cell_angle_beta                 82.374(7)
_cell_angle_gamma                68.567(8)
_cell_volume                     911.08(15)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    2472
_cell_measurement_theta_min      5.6610
_cell_measurement_theta_max      73.5270

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.737
_exptl_crystal_F_000             488
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.190
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.170
_exptl_absorpt_coefficient_mu    1.226
_shelx_estimated_absorpt_T_min   0.801
_shelx_estimated_absorpt_T_max   0.819
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  bruker-CCd
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4783
_diffrn_reflns_av_unetI/netI     0.0482
_diffrn_reflns_av_R_equivalents  0.0539
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         5.679
_diffrn_reflns_theta_max         65.989
_diffrn_reflns_theta_full        65.989
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measured_fraction_theta_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_point_group_measured_fraction_full 0.984
_reflns_number_total             3126
_reflns_number_gt                2610
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0021P)²+22.1231P] 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     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0212(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3126
_refine_ls_number_parameters     308
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1536
_refine_ls_R_factor_gt           0.1475
_refine_ls_wR_factor_ref         0.3408
_refine_ls_wR_factor_gt          0.3383
_refine_ls_goodness_of_fit_ref   1.154
_refine_ls_restrained_S_all      1.154
_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 0.6413(6) 0.4797(4) -0.1693(3) 0.0312(11) Uani 1 1 d . . . . .
H1WA H 0.6289 0.4400 -0.2276 0.037 Uiso 1 1 d R U . . .
O2 O 0.8561(6) 0.5382(4) 0.1704(3) 0.0333(11) Uani 1 1 d . . . . .
H2WA H 0.8693 0.5812 0.2273 0.040 Uiso 1 1 d R U . . .
N1 N 0.7556(7) 0.3946(5) -0.1075(3) 0.0249(12) Uani 1 1 d . . . . .
N2 N 0.8555(8) 0.2531(5) -0.1260(3) 0.0282(13) Uani 1 1 d . . . . .
N3 N 0.9492(8) 0.2031(5) -0.0521(3) 0.0314(14) Uani 1 1 d . . . . .
N4 N 0.9068(8) 0.3137(5) 0.0159(3) 0.0288(12) Uani 1 1 d . . . . .
N5 N 0.5814(7) 0.6945(5) -0.0134(3) 0.0279(12) Uani 1 1 d . . . . .
N6 N 0.5396(8) 0.8073(5) 0.0526(3) 0.0303(13) Uani 1 1 d . . . . .
N7 N 0.6362(8) 0.7612(5) 0.1260(3) 0.0286(13) Uani 1 1 d . . . . .
N8 N 0.7381(7) 0.6194(5) 0.1092(3) 0.0231(12) Uani 1 1 d . . . . .
C4 C 0.7892(8) 0.4321(5) -0.0201(4) 0.0187(12) Uani 1 1 d . . . . .
C5 C 0.7028(8) 0.5775(5) 0.0234(4) 0.0196(12) Uani 1 1 d . . . . .
O3 O 0.1537(6) 0.5149(4) 0.3221(3) 0.0317(10) Uani 1 1 d . . . . .
O4 O 0.3513(6) 0.4564(4) 0.6749(3) 0.0331(11) Uani 1 1 d . . . . .
N9 N 0.1906(7) 0.5959(5) 0.3892(3) 0.0248(11) Uani 1 1 d . . . . .
N10 N 0.1775(8) 0.7318(5) 0.3762(4) 0.0313(13) Uani 1 1 d . . . . .
N11 N 0.2218(8) 0.7761(5) 0.4570(4) 0.0324(13) Uani 1 1 d . . . . .
N12 N 0.2580(8) 0.6714(5) 0.5221(3) 0.0283(12) Uani 1 1 d . . . . .
N13 N 0.3109(7) 0.3786(5) 0.6082(3) 0.0240(11) Uani 1 1 d . . . . .
N14 N 0.3225(8) 0.2418(5) 0.6205(4) 0.0310(13) Uani 1 1 d . . . . .
N15 N 0.2764(8) 0.1998(5) 0.5401(4) 0.0318(13) Uani 1 1 d . . . . .
N16 N 0.2418(8) 0.3054(5) 0.4758(3) 0.0277(12) Uani 1 1 d . . . . .
C9 C 0.2609(8) 0.4195(6) 0.5180(4) 0.0245(13) Uani 1 1 d . . . . .
C10 C 0.2408(8) 0.5560(6) 0.4796(4) 0.0237(13) Uani 1 1 d . . . . .
N17 N 0.1595(8) 0.1888(5) 0.3026(4) 0.0343(14) Uani 1 1 d . . . . .
H17 H 0.1628 0.2557 0.3410 0.041 Uiso 1 1 d R U . . .
N18 N 0.1730(8) -0.0155(5) 0.2468(4) 0.0285(13) Uani 1 1 d . . . . .
H18 H 0.1885 -0.1061 0.2428 0.034 Uiso 1 1 d R U . . .
C6 C 0.1274(9) 0.0795(6) 0.1736(4) 0.0290(15) Uani 1 1 d . . . . .
H6 H 0.1042 0.0590 0.1104 0.035 Uiso 1 1 calc R U . . .
C7 C 0.1215(9) 0.2085(6) 0.2089(4) 0.0278(15) Uani 1 1 d . . . . .
H7 H 0.0958 0.2960 0.1749 0.033 Uiso 1 1 calc R U . . .
C8 C 0.1931(10) 0.0548(6) 0.3242(4) 0.0328(16) Uani 1 1 d . . . . .
H8 H 0.2262 0.0137 0.3847 0.039 Uiso 1 1 calc R U . . .
N19 N 0.6049(8) 0.2108(5) 0.1911(4) 0.0316(13) Uani 1 1 d . . . . .
H19 H 0.5735 0.2818 0.1525 0.038 Uiso 1 1 d R U . . .
N20 N 0.6758(8) -0.0016(5) 0.2478(3) 0.0294(13) Uani 1 1 d . . . . .
H20 H 0.6992 -0.0932 0.2522 0.035 Uiso 1 1 d R U . . .
C1 C 0.6246(9) 0.0753(6) 0.1696(4) 0.0284(15) Uani 1 1 d . . . . .
H1 H 0.6057 0.0395 0.1097 0.034 Uiso 1 1 calc R U . . .
C2 C 0.6862(9) 0.0903(6) 0.3192(4) 0.0312(15) Uani 1 1 d . . . . .
H2 H 0.7214 0.0644 0.3822 0.037 Uiso 1 1 calc R U . . .
C3 C 0.6379(9) 0.2219(6) 0.2835(5) 0.0296(15) Uani 1 1 d . . . . .
H3 H 0.6283 0.3083 0.3170 0.035 Uiso 1 1 calc R 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
O1 N1 1.338(6) . ?
O1 H1WA 0.9299 . ?
O2 N8 1.331(6) . ?
O2 H2WA 0.9301 . ?
N1 N2 1.325(6) . ?
N1 C4 1.346(7) . ?
N2 N3 1.298(7) . ?
N3 N4 1.366(7) . ?
N4 C4 1.311(7) . ?
N5 C5 1.317(7) . ?
N5 N6 1.365(7) . ?
N6 N7 1.295(7) . ?
N7 N8 1.327(6) . ?
N8 C5 1.347(7) . ?
C4 C5 1.438(7) . ?
O3 N9 1.344(6) . ?
O4 N13 1.332(6) . ?
N9 N10 1.322(7) . ?
N9 C10 1.366(7) . ?
N10 N11 1.323(8) . ?
N11 N12 1.343(7) . ?
N12 C10 1.339(8) . ?
N13 N14 1.333(7) . ?
N13 C9 1.364(7) . ?
N14 N15 1.315(7) . ?
N15 N16 1.340(7) . ?
N16 C9 1.333(8) . ?
C9 C10 1.409(8) . ?
N17 C8 1.295(8) . ?
N17 C7 1.360(8) . ?
N17 H17 0.8600 . ?
N18 C8 1.334(8) . ?
N18 C6 1.365(8) . ?
N18 H18 0.8600 . ?
C6 C7 1.350(9) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C8 H8 0.9500 . ?
N19 C1 1.324(8) . ?
N19 C3 1.345(8) . ?
N19 H19 0.8600 . ?
N20 C1 1.332(8) . ?
N20 C2 1.375(8) . ?
N20 H20 0.8601 . ?
C1 H1 0.9500 . ?
C2 C3 1.325(8) . ?
C2 H2 0.9500 . ?
C3 H3 0.9500 . ?

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 O1 H1WA 120.1 . . ?
N8 O2 H2WA 119.7 . . ?
N2 N1 O1 122.5(5) . . ?
N2 N1 C4 109.1(4) . . ?
O1 N1 C4 128.4(4) . . ?
N3 N2 N1 107.0(5) . . ?
N2 N3 N4 109.6(4) . . ?
C4 N4 N3 106.6(5) . . ?
C5 N5 N6 106.7(5) . . ?
N7 N6 N5 109.7(4) . . ?
N6 N7 N8 107.0(5) . . ?
N7 N8 O2 122.5(5) . . ?
N7 N8 C5 109.3(4) . . ?
O2 N8 C5 128.2(4) . . ?
N4 C4 N1 107.6(4) . . ?
N4 C4 C5 128.2(5) . . ?
N1 C4 C5 124.1(5) . . ?
N5 C5 N8 107.3(4) . . ?
N5 C5 C4 127.2(5) . . ?
N8 C5 C4 125.5(5) . . ?
N10 N9 O3 123.2(5) . . ?
N10 N9 C10 109.7(5) . . ?
O3 N9 C10 127.1(5) . . ?
N9 N10 N11 106.1(5) . . ?
N10 N11 N12 110.9(5) . . ?
C10 N12 N11 106.5(5) . . ?
O4 N13 N14 123.0(4) . . ?
O4 N13 C9 127.5(5) . . ?
N14 N13 C9 109.5(5) . . ?
N15 N14 N13 106.1(5) . . ?
N14 N15 N16 110.8(5) . . ?
C9 N16 N15 107.2(5) . . ?
N16 C9 N13 106.5(5) . . ?
N16 C9 C10 128.6(5) . . ?
N13 C9 C10 124.9(5) . . ?
N12 C10 N9 106.7(5) . . ?
N12 C10 C9 128.8(5) . . ?
N9 C10 C9 124.4(5) . . ?
C8 N17 C7 110.0(5) . . ?
C8 N17 H17 125.5 . . ?
C7 N17 H17 124.6 . . ?
C8 N18 C6 108.7(5) . . ?
C8 N18 H18 126.0 . . ?
C6 N18 H18 125.3 . . ?
C7 C6 N18 106.4(5) . . ?
C7 C6 H6 126.8 . . ?
N18 C6 H6 126.8 . . ?
C6 C7 N17 106.7(5) . . ?
C6 C7 H7 126.6 . . ?
N17 C7 H7 126.6 . . ?
N17 C8 N18 108.1(5) . . ?
N17 C8 H8 125.9 . . ?
N18 C8 H8 125.9 . . ?
C1 N19 C3 109.8(5) . . ?
C1 N19 H19 125.3 . . ?
C3 N19 H19 124.9 . . ?
C1 N20 C2 108.3(5) . . ?
C1 N20 H20 125.5 . . ?
C2 N20 H20 126.2 . . ?
N19 C1 N20 107.2(5) . . ?
N19 C1 H1 126.4 . . ?
N20 C1 H1 126.4 . . ?
C3 C2 N20 107.1(5) . . ?
C3 C2 H2 126.4 . . ?
N20 C2 H2 126.4 . . ?
C2 C3 N19 107.6(5) . . ?
C2 C3 H3 126.2 . . ?
N19 C3 H3 126.2 . . ?

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
O1 N1 N2 N3 -179.6(5) . . . . ?
C4 N1 N2 N3 0.1(7) . . . . ?
N1 N2 N3 N4 0.9(7) . . . . ?
N2 N3 N4 C4 -1.6(7) . . . . ?
C5 N5 N6 N7 1.5(7) . . . . ?
N5 N6 N7 N8 -0.8(7) . . . . ?
N6 N7 N8 O2 179.1(5) . . . . ?
N6 N7 N8 C5 -0.1(7) . . . . ?
N3 N4 C4 N1 1.6(6) . . . . ?
N3 N4 C4 C5 179.9(6) . . . . ?
N2 N1 C4 N4 -1.1(7) . . . . ?
O1 N1 C4 N4 178.6(5) . . . . ?
N2 N1 C4 C5 -179.5(5) . . . . ?
O1 N1 C4 C5 0.1(9) . . . . ?
N6 N5 C5 N8 -1.5(6) . . . . ?
N6 N5 C5 C4 -179.4(6) . . . . ?
N7 N8 C5 N5 1.0(6) . . . . ?
O2 N8 C5 N5 -178.1(5) . . . . ?
N7 N8 C5 C4 179.0(5) . . . . ?
O2 N8 C5 C4 -0.1(9) . . . . ?
N4 C4 C5 N5 -178.4(6) . . . . ?
N1 C4 C5 N5 -0.3(10) . . . . ?
N4 C4 C5 N8 4.0(10) . . . . ?
N1 C4 C5 N8 -177.9(5) . . . . ?
O3 N9 N10 N11 179.3(5) . . . . ?
C10 N9 N10 N11 0.9(6) . . . . ?
N9 N10 N11 N12 -1.5(6) . . . . ?
N10 N11 N12 C10 1.6(6) . . . . ?
O4 N13 N14 N15 -178.9(5) . . . . ?
C9 N13 N14 N15 -1.3(6) . . . . ?
N13 N14 N15 N16 1.9(6) . . . . ?
N14 N15 N16 C9 -1.9(6) . . . . ?
N15 N16 C9 N13 1.0(6) . . . . ?
N15 N16 C9 C10 179.4(6) . . . . ?
O4 N13 C9 N16 177.6(5) . . . . ?
N14 N13 C9 N16 0.2(6) . . . . ?
O4 N13 C9 C10 -0.8(9) . . . . ?
N14 N13 C9 C10 -178.3(5) . . . . ?
N11 N12 C10 N9 -1.0(6) . . . . ?
N11 N12 C10 C9 -178.7(6) . . . . ?
N10 N9 C10 N12 0.1(6) . . . . ?
O3 N9 C10 N12 -178.3(5) . . . . ?
N10 N9 C10 C9 177.9(5) . . . . ?
O3 N9 C10 C9 -0.4(9) . . . . ?
N16 C9 C10 N12 179.3(6) . . . . ?
N13 C9 C10 N12 -2.6(10) . . . . ?
N16 C9 C10 N9 1.9(9) . . . . ?
N13 C9 C10 N9 -180.0(5) . . . . ?
C8 N18 C6 C7 0.3(7) . . . . ?
N18 C6 C7 N17 -1.2(7) . . . . ?
C8 N17 C7 C6 1.7(7) . . . . ?
C7 N17 C8 N18 -1.6(7) . . . . ?
C6 N18 C8 N17 0.8(7) . . . . ?
C3 N19 C1 N20 -1.7(7) . . . . ?
C2 N20 C1 N19 0.4(7) . . . . ?
C1 N20 C2 C3 1.0(7) . . . . ?
N20 C2 C3 N19 -2.0(7) . . . . ?
C1 N19 C3 C2 2.3(7) . . . . ?

_refine_diff_density_max         0.709
_refine_diff_density_min         -0.743
_refine_diff_density_rms         0.173

####################################################################### 
# 
# 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_111
_database_code_depnum_ccdc_archive 'CCDC 1872564'
loop_
_audit_author_name
_audit_author_address
'Zhang jinhao'
;SWUST
China
;
_audit_update_record             
;
2018-10-11 deposited with the CCDC.	2019-07-02 downloaded from the CCDC.
;
_audit_creation_date             2018-07-10
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C2 H2 N8 O2, C3 H4 N3'
_chemical_formula_sum            'C5 H6 N11 O2'
_chemical_formula_weight         252.21
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   7.4215(5)
_cell_length_b                   9.2025(6)
_cell_length_c                   13.7986(9)
_cell_angle_alpha                90
_cell_angle_beta                 98.745(2)
_cell_angle_gamma                90
_cell_volume                     931.44(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6755
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.549
_cell_measurement_theta_min      2.987
_shelx_estimated_absorpt_T_max   0.983
_shelx_estimated_absorpt_T_min   0.960
_exptl_absorpt_coefficient_mu    0.147
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.7160
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0604 before and 0.0351 after correction.
The Ratio of minimum to maximum transmission is 0.9603.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.799
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             516
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0168
_diffrn_reflns_av_unetI/netI     0.0096
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            8078
_diffrn_reflns_point_group_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.569
_diffrn_reflns_theta_min         3.552
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1010
_reflns_number_total             1066
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.883
_refine_diff_density_min         -0.576
_refine_diff_density_rms         0.091
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.123
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     84
_refine_ls_number_reflns         1066
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0623
_refine_ls_R_factor_gt           0.0609
_refine_ls_restrained_S_all      1.123
_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)+(0.1263P)²+1.9922P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1995
_refine_ls_wR_factor_ref         0.2009
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H) groups
 At 1.5 times of:
  All O(H) groups
2. Restrained distances
 H1_$1-H1
 2.2 with sigma of 0.02
3. Others
 Fixed Sof: H5A(0.5) H5B(0.5)
4.a Aromatic/amide H refined with riding coordinates:
 C3(H3)
4.b X=CH2 refined with riding coordinates:
 N5(H5A,H5B)
4.c Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_atom_sites_solution_hydrogens   geom
_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 0.6484(2) 0.5258(2) 0.47580(15) 0.0335(6) Uani 1 1 d . . . . .
H1 H 0.577241 0.472403 0.441112 0.050 Uiso 1 1 calc DGR . . . .
N1 N 0.7755(2) 0.4460(2) 0.52931(14) 0.0195(5) Uani 1 1 d . . . . .
C3 C 0.6182(3) 0.2850(2) 0.80327(14) 0.0154(5) Uani 1 1 d . . . . .
H3 H 0.717649 0.314710 0.848181 0.019 Uiso 1 1 calc R . . . .
N4 N 1.0321(3) 0.3525(2) 0.59328(14) 0.0233(5) Uani 1 1 d . . . . .
N2 N 0.7380(3) 0.3443(2) 0.59264(15) 0.0251(5) Uani 1 1 d . . . . .
N3 N 0.8944(3) 0.2890(2) 0.63054(15) 0.0266(6) Uani 1 1 d . . . . .
C1 C 0.9558(3) 0.4511(2) 0.52965(15) 0.0176(5) Uani 1 1 d . . . . .
N5 N 0.500000 0.5165(3) 0.750000 0.0308(7) Uani 1 2 d S T P . .
H5A H 0.416589 0.563191 0.712402 0.037 Uiso 0.5 1 calc R . . . .
H5B H 0.583411 0.563191 0.787598 0.037 Uiso 0.5 1 calc R . . . .
N6 N 0.5714(3) 0.1448(2) 0.78204(18) 0.0321(6) Uani 1 1 d . . . . .
C2 C 0.500000 0.3739(3) 0.750000 0.0188(6) Uani 1 2 d S T P . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 N1 1.327(2) . ?
N1 N2 1.339(3) . ?
N1 C1 1.339(3) . ?
C3 N6 1.356(3) . ?
C3 C2 1.335(3) . ?
N4 N3 1.345(3) . ?
N4 C1 1.328(3) . ?
N2 N3 1.302(3) . ?
C1 C1 1.440(4) 5_766 ?
N5 C2 1.312(4) . ?
N6 N6 1.272(4) 2_656 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 N1 N2 123.33(18) . . ?
O1 N1 C1 127.46(18) . . ?
N2 N1 C1 109.20(18) . . ?
C2 C3 N6 109.80(19) . . ?
C1 N4 N3 106.10(17) . . ?
N3 N2 N1 105.92(18) . . ?
N2 N3 N4 111.06(18) . . ?
N1 C1 C1 124.2(2) . 5_766 ?
N4 C1 N1 107.71(18) . . ?
N4 C1 C1 128.1(2) . 5_766 ?
N6 N6 C3 107.99(12) 2_656 . ?
C3 C2 C3 104.4(3) 2_656 . ?
N5 C2 C3 127.79(13) . 2_656 ?
N5 C2 C3 127.80(13) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 N1 N2 N3 179.6(2) . . . . ?
O1 N1 C1 N4 -179.6(2) . . . . ?
O1 N1 C1 C1 0.7(4) . . . 5_766 ?
N1 N2 N3 N4 0.0(3) . . . . ?
N2 N1 C1 N4 0.0(2) . . . . ?
N2 N1 C1 C1 -179.7(3) . . . 5_766 ?
N3 N4 C1 N1 0.0(2) . . . . ?
N3 N4 C1 C1 179.7(3) . . . 5_766 ?
C1 N1 N2 N3 0.0(3) . . . . ?
C1 N4 N3 N2 0.0(3) . . . . ?
N6 C3 C2 C3 0.06(13) . . . 2_656 ?
N6 C3 C2 N5 -179.94(13) . . . . ?
C2 C3 N6 N6 -0.2(4) . . . 2_656 ?

_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_44
_database_code_depnum_ccdc_archive 'CCDC 1879814'
loop_
_audit_author_name
_audit_author_address
'Zhang jinhao'
;SWUST
China
;
_audit_update_record             
;
2018-11-19 deposited with the CCDC.	2019-07-02 downloaded from the CCDC.
;
_audit_creation_date             2018-11-12
_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            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C2 H N8 O2, C H7 N4'
_chemical_formula_sum            'C3 H8 N12 O2'
_chemical_formula_weight         244.21
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   7.3674(7)
_cell_length_b                   6.5154(6)
_cell_length_c                   20.4844(18)
_cell_angle_alpha                90
_cell_angle_beta                 98.532(2)
_cell_angle_gamma                90
_cell_volume                     972.40(15)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2891
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      24.606
_cell_measurement_theta_min      3.108
_shelx_estimated_absorpt_T_max   0.979
_shelx_estimated_absorpt_T_min   0.977
_exptl_absorpt_coefficient_mu    0.140
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6518
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0629 before and 0.0553 after correction.
The Ratio of minimum to maximum transmission is 0.8742.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.668
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             504
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.15
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0485
_diffrn_reflns_av_unetI/netI     0.0426
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            9274
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.006
_diffrn_reflns_theta_max         25.006
_diffrn_reflns_theta_min         3.109
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1176
_reflns_number_total             1715
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.218
_refine_diff_density_min         -0.307
_refine_diff_density_rms         0.055
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.095
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     166
_refine_ls_number_reflns         1715
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0868
_refine_ls_R_factor_gt           0.0503
_refine_ls_restrained_S_all      1.096
_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)+(0.0575P)²+0.2672P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1102
_refine_ls_wR_factor_ref         0.1233
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All N(H) groups, All N(H,H) groups
2. Restrained distances
 O1-H1
 0.86 with sigma of 0.02
 N12-H12B
 0.86 with sigma of 0.02
 N12-H12A
 0.86 with sigma of 0.02
3.a Aromatic/amide H refined with riding coordinates:
 N11(H11)
3.b X=CH2 refined with riding coordinates:
 N9(H9A,H9B), N10(H10A,H10B)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 1.0762(2) 0.6279(4) 0.23469(9) 0.0607(7) Uani 1 1 d D . . . .
H1 H 1.181(4) 0.625(7) 0.2174(17) 0.142(19) Uiso 1 1 d D . . . .
O2 O 0.3724(2) 0.6421(3) 0.19516(8) 0.0472(6) Uani 1 1 d . . . . .
N1 N 0.6848(3) 0.5404(3) 0.12441(9) 0.0373(6) Uani 1 1 d . . . . .
N2 N 0.8181(3) 0.5445(4) 0.08626(10) 0.0430(6) Uani 1 1 d . . . . .
N3 N 0.9783(3) 0.5763(4) 0.12170(10) 0.0434(6) Uani 1 1 d . . . . .
N4 N 0.9461(3) 0.5919(3) 0.18355(10) 0.0347(5) Uani 1 1 d . . . . .
N5 N 0.7639(3) 0.5575(3) 0.30675(10) 0.0343(6) Uani 1 1 d . . . . .
N6 N 0.6322(3) 0.5807(3) 0.34406(10) 0.0386(6) Uani 1 1 d . . . . .
N7 N 0.4730(3) 0.6144(4) 0.30826(10) 0.0395(6) Uani 1 1 d . . . . .
N8 N 0.5039(2) 0.6137(3) 0.24590(9) 0.0314(5) Uani 1 1 d . . . . .
N9 N 0.8195(3) 0.7912(4) 0.53777(11) 0.0578(7) Uani 1 1 d . . . . .
H9A H 0.7868 0.8541 0.5010 0.069 Uiso 1 1 calc R . . . .
H9B H 0.8636 0.8594 0.5725 0.069 Uiso 1 1 calc R . . . .
N10 N 0.7352(3) 0.4824(4) 0.48909(10) 0.0507(7) Uani 1 1 d . . . . .
H10A H 0.7017 0.5424 0.4518 0.061 Uiso 1 1 calc R . . . .
H10B H 0.7249 0.3514 0.4922 0.061 Uiso 1 1 calc R . . . .
N11 N 0.8540(3) 0.4961(4) 0.59773(10) 0.0415(6) Uani 1 1 d . . . . .
H11 H 0.8957 0.5651 0.6325 0.050 Uiso 1 1 calc R . . . .
N12 N 0.8403(4) 0.2833(4) 0.60041(12) 0.0463(7) Uani 1 1 d D . . . .
H12A H 0.766(4) 0.245(5) 0.6275(13) 0.070(11) Uiso 1 1 d D . . . .
H12B H 0.947(3) 0.228(5) 0.6158(16) 0.082(12) Uiso 1 1 d D . . . .
C1 C 0.7663(3) 0.5707(4) 0.18537(11) 0.0270(6) Uani 1 1 d . . . . .
C2 C 0.6822(3) 0.5795(4) 0.24488(11) 0.0262(6) Uani 1 1 d . . . . .
C3 C 0.8019(3) 0.5904(4) 0.54099(11) 0.0325(6) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 H1 0.897(19) . ?
O1 N4 1.332(2) . ?
O2 N8 1.325(2) . ?
N1 N2 1.343(3) . ?
N1 C1 1.318(3) . ?
N2 N3 1.308(3) . ?
N3 N4 1.327(3) . ?
N4 C1 1.338(3) . ?
N5 N6 1.330(3) . ?
N5 C2 1.328(3) . ?
N6 N7 1.307(3) . ?
N7 N8 1.330(3) . ?
N8 C2 1.335(3) . ?
N9 H9A 0.8600 . ?
N9 H9B 0.8600 . ?
N9 C3 1.317(3) . ?
N10 H10A 0.8600 . ?
N10 H10B 0.8600 . ?
N10 C3 1.309(3) . ?
N11 H11 0.8600 . ?
N11 N12 1.392(3) . ?
N11 C3 1.320(3) . ?
N12 H12A 0.871(18) . ?
N12 H12B 0.878(18) . ?
C1 C2 1.448(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
N4 O1 H1 104(2) . . ?
C1 N1 N2 106.21(19) . . ?
N3 N2 N1 110.97(19) . . ?
N2 N3 N4 105.51(19) . . ?
O1 N4 C1 126.6(2) . . ?
N3 N4 O1 123.68(19) . . ?
N3 N4 C1 109.7(2) . . ?
C2 N5 N6 105.67(18) . . ?
N7 N6 N5 111.56(18) . . ?
N6 N7 N8 105.71(19) . . ?
O2 N8 N7 122.91(18) . . ?
O2 N8 C2 128.15(19) . . ?
N7 N8 C2 108.94(19) . . ?
H9A N9 H9B 120.0 . . ?
C3 N9 H9A 120.0 . . ?
C3 N9 H9B 120.0 . . ?
H10A N10 H10B 120.0 . . ?
C3 N10 H10A 120.0 . . ?
C3 N10 H10B 120.0 . . ?
N12 N11 H11 120.5 . . ?
C3 N11 H11 120.5 . . ?
C3 N11 N12 119.0(2) . . ?
N11 N12 H12A 112(2) . . ?
N11 N12 H12B 111(2) . . ?
H12A N12 H12B 105(3) . . ?
N1 C1 N4 107.6(2) . . ?
N1 C1 C2 127.8(2) . . ?
N4 C1 C2 124.6(2) . . ?
N5 C2 N8 108.1(2) . . ?
N5 C2 C1 127.5(2) . . ?
N8 C2 C1 124.3(2) . . ?
N9 C3 N11 119.2(2) . . ?
N10 C3 N9 121.4(2) . . ?
N10 C3 N11 119.3(3) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
