# 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_mo_4_0m
_database_code_depnum_ccdc_archive 'CCDC 1903599'
loop_
_audit_author_name
_audit_author_address
'Yuangang Xu'
;Nanjing University of Science and Technology
China
;
_audit_update_record             
;
2019-03-16 deposited with the CCDC.	2019-05-28 downloaded from the CCDC.
;
_audit_creation_date             2016-12-05
_audit_creation_method           
;
Olex2 1.2-alpha
(compiled 2016.11.24 svn.r3356 for OlexSys, GUI svn.r5267)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         '2(C2 H N8 O2), C4 H10 N10'
_chemical_formula_sum            'C8 H12 N26 O4'
_chemical_formula_weight         536.44
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   6.4179(5)
_cell_length_b                   7.4575(5)
_cell_length_c                   10.8598(8)
_cell_angle_alpha                74.881(5)
_cell_angle_beta                 74.297(5)
_cell_angle_gamma                88.026(6)
_cell_volume                     482.68(6)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    1998
_cell_measurement_temperature    205
_cell_measurement_theta_max      26.95
_cell_measurement_theta_min      2.83
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.153
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6750
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0616 before and 0.0507 after correction.
The Ratio of minimum to maximum transmission is 0.9053.
The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.845
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             274
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0932
_diffrn_reflns_av_unetI/netI     0.0715
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            8188
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.797
_diffrn_reflns_theta_min         2.018
_diffrn_ambient_temperature      205
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1479
_reflns_number_total             2264
_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 v7.68A (Bruker, 2009)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_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         0.648
_refine_diff_density_min         -0.652
_refine_diff_density_rms         0.085
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     177
_refine_ls_number_reflns         2264
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0902
_refine_ls_R_factor_gt           0.0579
_refine_ls_restrained_S_all      1.009
_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)+(0.1029P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1584
_refine_ls_wR_factor_ref         0.1748
_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
 0.85 with sigma of 0.02
 H4A-H1B
 2.3 with sigma of 0.02
3.a Rotating group:
 N4(H4A,H4B)
3.b Aromatic/amide H refined with riding coordinates:
 N1AA(H1AA)
3.c X=CH2 refined with riding coordinates:
 N1(H1A,H1B)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
_atom_sites_special_details      
;
The structure was solved using Direct Methods (ShelXS). RE = 0.2, Nqual =  -1, Ralpha = 0.032
;
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 1.3327(4) 0.0873(3) 0.4057(2) 0.0387(6) Uani 1 1 d D . . . .
N2 N 1.1383(4) 0.0631(3) 0.6261(2) 0.0302(6) Uani 1 1 d . . . . .
N3 N 1.0765(4) 0.1815(3) 0.6965(2) 0.0317(6) Uani 1 1 d . . . . .
O4 O 1.2608(3) 0.7465(3) 0.4881(2) 0.0340(5) Uani 1 1 d . . . . .
N3AA N -0.0780(3) 0.8329(3) 0.9152(2) 0.0202(5) Uani 1 1 d . . . . .
N0AA N 0.2444(4) 0.8840(3) 0.9390(2) 0.0251(5) Uani 1 1 d . . . . .
N1AA N 0.2532(4) 0.7528(3) 0.8693(2) 0.0262(5) Uani 1 1 d . . . . .
H1AA H 0.3697 0.6968 0.8395 0.031 Uiso 1 1 calc R . . . .
N4AA N 1.3414(4) 0.6717(3) 0.3887(2) 0.0250(5) Uani 1 1 d . . . . .
N2AA N 1.2447(4) 0.1620(3) 0.5053(2) 0.0258(5) Uani 1 1 d . . . . .
N6 N 1.1433(4) 0.3573(3) 0.6237(2) 0.0271(5) Uani 1 1 d . . . . .
N1 N -0.0021(4) 0.6060(3) 0.7961(2) 0.0317(6) Uani 1 1 d . . . . .
H1A H 0.0913 0.5335 0.7611 0.038 Uiso 1 1 calc R . . . .
H1B H -0.1359 0.6016 0.7932 0.038 Uiso 1 1 calc DR . . . .
C0AA C 0.0595(4) 0.7229(4) 0.8536(2) 0.0227(6) Uani 1 1 d . . . . .
C1AA C 0.0440(4) 0.9301(3) 0.9649(2) 0.0201(6) Uani 1 1 d . . . . .
N4 N -0.2912(4) 0.8454(3) 0.9085(2) 0.0245(5) Uani 1 1 d . . . . .
H4A H -0.2928 0.8705 0.8265 0.029 Uiso 1 1 d DGR . . . .
H4B H -0.3618 0.7412 0.9506 0.029 Uiso 1 1 d GR . . . .
N5 N 1.4375(4) 0.7736(3) 0.2656(2) 0.0304(6) Uani 1 1 d . . . . .
C6 C 1.3442(4) 0.4928(3) 0.3891(3) 0.0219(6) Uani 1 1 d . . . . .
C7 C 1.2474(4) 0.3429(3) 0.5031(2) 0.0213(6) Uani 1 1 d . . . . .
N8 N 1.4989(4) 0.6571(3) 0.1940(2) 0.0326(6) Uani 1 1 d . . . . .
N9 N 1.4439(4) 0.4806(3) 0.2660(2) 0.0285(6) Uani 1 1 d . . . . .
H1 H 1.308(9) -0.029(3) 0.450(5) 0.11(2) Uiso 1 1 d D . . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0620(15) 0.0194(11) 0.0312(12) -0.0145(9) 0.0014(10) -0.0022(10)
N2 0.0387(14) 0.0183(11) 0.0281(13) -0.0013(10) -0.0037(11) -0.0059(10)
N3 0.0395(14) 0.0241(12) 0.0263(13) -0.0042(10) -0.0026(11) -0.0004(10)
O4 0.0485(13) 0.0213(10) 0.0298(11) -0.0124(9) -0.0006(9) -0.0017(9)
N3AA 0.0219(11) 0.0170(10) 0.0202(11) -0.0059(9) -0.0023(9) -0.0012(8)
N0AA 0.0271(12) 0.0233(12) 0.0270(12) -0.0127(10) -0.0049(9) 0.0017(9)
N1AA 0.0264(12) 0.0251(12) 0.0293(12) -0.0161(10) -0.0030(10) 0.0026(9)
N4AA 0.0308(12) 0.0174(11) 0.0260(12) -0.0079(10) -0.0040(10) -0.0006(9)
N2AA 0.0350(13) 0.0182(11) 0.0239(12) -0.0083(10) -0.0044(10) -0.0020(9)
N6 0.0333(13) 0.0198(11) 0.0250(12) -0.0058(10) -0.0029(10) 0.0009(9)
N1 0.0303(13) 0.0312(13) 0.0401(14) -0.0250(12) -0.0055(11) 0.0030(10)
C0AA 0.0273(14) 0.0203(13) 0.0185(13) -0.0077(11) -0.0006(10) 0.0001(10)
C1AA 0.0245(13) 0.0163(12) 0.0187(13) -0.0061(10) -0.0027(10) -0.0006(10)
N4 0.0256(12) 0.0248(12) 0.0245(11) -0.0088(10) -0.0065(9) -0.0020(9)
N5 0.0374(13) 0.0199(12) 0.0265(13) -0.0019(10) -0.0002(10) -0.0021(10)
C6 0.0253(13) 0.0151(12) 0.0267(14) -0.0070(11) -0.0076(11) -0.0013(10)
C7 0.0270(13) 0.0158(12) 0.0216(13) -0.0072(10) -0.0052(11) 0.0006(10)
N8 0.0422(14) 0.0246(13) 0.0275(13) -0.0078(11) -0.0023(11) -0.0006(10)
N9 0.0339(13) 0.0229(12) 0.0250(12) -0.0061(10) -0.0014(10) -0.0028(10)

_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 N2AA 1.328(3) . ?
O1 H1 0.87(2) . ?
N2 N3 1.299(3) . ?
N2 N2AA 1.332(3) . ?
N3 N6 1.357(3) . ?
O4 N4AA 1.317(3) . ?
N3AA C0AA 1.348(3) . ?
N3AA C1AA 1.379(3) . ?
N3AA N4 1.388(3) . ?
N0AA N1AA 1.376(3) . ?
N0AA C1AA 1.294(3) . ?
N1AA H1AA 0.8700 . ?
N1AA C0AA 1.334(4) . ?
N4AA N5 1.342(3) . ?
N4AA C6 1.333(3) . ?
N2AA C7 1.343(3) . ?
N6 C7 1.329(3) . ?
N1 H1A 0.8700 . ?
N1 H1B 0.8700 . ?
N1 C0AA 1.322(3) . ?
C1AA C1AA 1.459(5) 2_577 ?
N4 H4A 0.8637 . ?
N4 H4B 0.8637 . ?
N5 N8 1.295(3) . ?
C6 C7 1.442(4) . ?
C6 N9 1.342(3) . ?
N8 N9 1.347(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
N2AA O1 H1 98(4) . . ?
N3 N2 N2AA 106.3(2) . . ?
N2 N3 N6 111.0(2) . . ?
C0AA N3AA C1AA 106.2(2) . . ?
C0AA N3AA N4 121.0(2) . . ?
C1AA N3AA N4 132.4(2) . . ?
C1AA N0AA N1AA 104.6(2) . . ?
N0AA N1AA H1AA 124.5 . . ?
C0AA N1AA N0AA 111.0(2) . . ?
C0AA N1AA H1AA 124.5 . . ?
O4 N4AA N5 122.6(2) . . ?
O4 N4AA C6 128.6(2) . . ?
C6 N4AA N5 108.8(2) . . ?
O1 N2AA N2 123.5(2) . . ?
O1 N2AA C7 127.1(2) . . ?
N2 N2AA C7 109.4(2) . . ?
C7 N6 N3 105.7(2) . . ?
H1A N1 H1B 120.0 . . ?
C0AA N1 H1A 120.0 . . ?
C0AA N1 H1B 120.0 . . ?
N1AA C0AA N3AA 106.5(2) . . ?
N1 C0AA N3AA 123.3(3) . . ?
N1 C0AA N1AA 130.1(3) . . ?
N3AA C1AA C1AA 123.4(3) . 2_577 ?
N0AA C1AA N3AA 111.6(2) . . ?
N0AA C1AA C1AA 125.0(3) . 2_577 ?
N3AA N4 H4A 109.1 . . ?
N3AA N4 H4B 110.3 . . ?
H4A N4 H4B 108.8 . . ?
N8 N5 N4AA 106.4(2) . . ?
N4AA C6 C7 124.5(2) . . ?
N4AA C6 N9 108.2(2) . . ?
N9 C6 C7 127.3(2) . . ?
N2AA C7 C6 125.6(2) . . ?
N6 C7 N2AA 107.6(2) . . ?
N6 C7 C6 126.8(2) . . ?
N5 N8 N9 111.4(2) . . ?
C6 N9 N8 105.3(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 N2AA C7 N6 -179.3(2) . . . . ?
O1 N2AA C7 C6 1.4(4) . . . . ?
N2 N3 N6 C7 1.0(3) . . . . ?
N2 N2AA C7 N6 0.5(3) . . . . ?
N2 N2AA C7 C6 -178.8(2) . . . . ?
N3 N2 N2AA O1 179.9(2) . . . . ?
N3 N2 N2AA C7 0.1(3) . . . . ?
N3 N6 C7 N2AA -0.9(3) . . . . ?
N3 N6 C7 C6 178.5(2) . . . . ?
O4 N4AA N5 N8 179.4(2) . . . . ?
O4 N4AA C6 C7 2.5(4) . . . . ?
O4 N4AA C6 N9 -179.7(2) . . . . ?
N0AA N1AA C0AA N3AA -0.9(3) . . . . ?
N0AA N1AA C0AA N1 -178.2(3) . . . . ?
N1AA N0AA C1AA N3AA 0.3(3) . . . . ?
N1AA N0AA C1AA C1AA -178.4(3) . . . 2_577 ?
N4AA N5 N8 N9 0.7(3) . . . . ?
N4AA C6 C7 N2AA 178.8(2) . . . . ?
N4AA C6 C7 N6 -0.4(4) . . . . ?
N4AA C6 N9 N8 -0.1(3) . . . . ?
N2AA N2 N3 N6 -0.7(3) . . . . ?
C0AA N3AA C1AA N0AA -0.9(3) . . . . ?
C0AA N3AA C1AA C1AA 177.8(3) . . . 2_577 ?
C1AA N3AA C0AA N1AA 1.1(3) . . . . ?
C1AA N3AA C0AA N1 178.5(2) . . . . ?
C1AA N0AA N1AA C0AA 0.4(3) . . . . ?
N4 N3AA C0AA N1AA 175.0(2) . . . . ?
N4 N3AA C0AA N1 -7.5(4) . . . . ?
N4 N3AA C1AA N0AA -173.8(2) . . . . ?
N4 N3AA C1AA C1AA 4.9(5) . . . 2_577 ?
N5 N4AA C6 C7 -177.3(2) . . . . ?
N5 N4AA C6 N9 0.5(3) . . . . ?
N5 N8 N9 C6 -0.4(3) . . . . ?
C6 N4AA N5 N8 -0.7(3) . . . . ?
C7 C6 N9 N8 177.7(3) . . . . ?
N9 C6 C7 N2AA 1.4(4) . . . . ?
N9 C6 C7 N6 -177.8(3) . . . . ?

_shelx_res_file                  
;
    mo_4_0m.res created by SHELXL-2014/7

TITL mo_4_0m in P-1
CELL 0.71073 6.4179 7.4575 10.8598 74.881 74.297 88.026
ZERR 1 0.0005 0.0005 0.0008 0.005 0.005 0.006
LATT 1
SFAC C H N O
UNIT 8 12 26 4
DFIX 0.85 O1 H1
DFIX 2.3 H4a H1b

L.S. 15
PLAN  -3 0 0
TEMP -68.15
HTAB
BOND $H
CONF
MORE -1
fmap 2
acta
REM <olex2.extras>
REM <HklSrc "%.\\mo_4_0m.hkl">
REM </olex2.extras>

WGHT    0.102900
FVAR       0.73665
O1    4    1.332689    0.087277    0.405660    11.00000    0.06196    0.01942 =
         0.03122   -0.01453    0.00142   -0.00220
N2    3    1.138280    0.063118    0.626065    11.00000    0.03873    0.01828 =
         0.02810   -0.00134   -0.00368   -0.00585
N3    3    1.076504    0.181541    0.696521    11.00000    0.03948    0.02413 =
         0.02632   -0.00416   -0.00257   -0.00043
O4    4    1.260831    0.746489    0.488091    11.00000    0.04846    0.02126 =
         0.02984   -0.01241   -0.00057   -0.00171
N3AA  3   -0.078034    0.832942    0.915179    11.00000    0.02192    0.01702 =
         0.02024   -0.00591   -0.00230   -0.00117
N0AA  3    0.244382    0.884046    0.939001    11.00000    0.02707    0.02328 =
         0.02698   -0.01274   -0.00495    0.00173
N1AA  3    0.253200    0.752819    0.869326    11.00000    0.02636    0.02511 =
         0.02933   -0.01608   -0.00300    0.00262
AFIX  43
H1AA  2    0.369725    0.696797    0.839456    11.00000   -1.20000
AFIX   0

N4AA  3    1.341449    0.671719    0.388746    11.00000    0.03081    0.01741 =
         0.02597   -0.00795   -0.00397   -0.00055
N2AA  3    1.244698    0.162033    0.505350    11.00000    0.03502    0.01822 =
         0.02385   -0.00826   -0.00438   -0.00201
N6    3    1.143287    0.357306    0.623679    11.00000    0.03331    0.01984 =
         0.02503   -0.00580   -0.00288    0.00088
N1    3   -0.002077    0.605999    0.796118    11.00000    0.03035    0.03124 =
         0.04014   -0.02498   -0.00554    0.00299
AFIX  93
H1A   2    0.091256    0.533520    0.761137    11.00000   -1.20000
H1B   2   -0.135911    0.601554    0.793235    11.00000   -1.20000
AFIX   0
C0AA  1    0.059452    0.722861    0.853640    11.00000    0.02729    0.02034 =
         0.01851   -0.00765   -0.00055    0.00009
C1AA  1    0.043985    0.930089    0.964921    11.00000    0.02446    0.01630 =
         0.01866   -0.00610   -0.00266   -0.00061
N4    3   -0.291157    0.845421    0.908474    11.00000    0.02558    0.02478 =
         0.02446   -0.00881   -0.00646   -0.00203
AFIX   7
H4A   2   -0.292755    0.870527    0.826473    11.00000   -1.20000
H4B   2   -0.361849    0.741183    0.950638    11.00000   -1.20000
AFIX   0

N5    3    1.437494    0.773560    0.265649    11.00000    0.03740    0.01995 =
         0.02646   -0.00193   -0.00020   -0.00206
C6    1    1.344178    0.492813    0.389107    11.00000    0.02532    0.01509 =
         0.02671   -0.00696   -0.00762   -0.00129
C7    1    1.247359    0.342877    0.503106    11.00000    0.02704    0.01581 =
         0.02158   -0.00719   -0.00520    0.00061
N8    3    1.498910    0.657131    0.193970    11.00000    0.04218    0.02456 =
         0.02748   -0.00781   -0.00225   -0.00061
N9    3    1.443885    0.480582    0.265994    11.00000    0.03394    0.02291 =
         0.02498   -0.00612   -0.00136   -0.00275
H1    2    1.308209   -0.029126    0.449889    11.00000    0.11197
HKLF 4

REM  mo_4_0m in P-1
REM R1 =  0.0579 for    1479 Fo > 4sig(Fo)  and  0.0902 for all    2264 data
REM    177 parameters refined using      2 restraints

END

WGHT      0.1029      0.0000

REM Instructions for potential hydrogen bonds
EQIV $1 -x+2, -y+1, -z+1
HTAB N1AA N9_$1
EQIV $2 x-1, y, z
HTAB N1 N6_$2
EQIV $3 -x+1, -y+1, -z+1
HTAB N1 N9_$3
HTAB N4 O1_$3
EQIV $4 x-2, y, z+1
HTAB N4 N8_$4
EQIV $5 x, y-1, z
HTAB O1 O4_$5
HTAB O1 N4AA_$5

REM Highest difference peak  0.648,  deepest hole -0.652,  1-sigma level  0.085
Q1    1  -0.3882  0.8214  0.9954  11.00000  0.05    0.65
Q2    1  -0.3121  0.9636  0.8633  11.00000  0.05    0.58
Q3    1   1.4286  0.4860  0.1836  11.00000  0.05    0.45
;
_shelx_res_checksum              22608
_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_zz
_database_code_depnum_ccdc_archive 'CCDC 1903600'
loop_
_audit_author_name
_audit_author_address
'Yuangang Xu'
;Nanjing University of Science and Technology
China
;
_audit_update_record             
;
2019-03-16 deposited with the CCDC.	2019-05-28 downloaded from the CCDC.
;
_audit_creation_date             2016-12-04
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2016.11.24 svn.r3356 for OlexSys, GUI svn.r5267)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C2 N8 O2, 2(H2 O), C4 H10 N10'
_chemical_formula_sum            'C6 H14 N18 O4'
_chemical_formula_weight         402.35
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   8.9135(17)
_cell_length_b                   14.392(3)
_cell_length_c                   6.7544(14)
_cell_angle_alpha                90
_cell_angle_beta                 110.499(4)
_cell_angle_gamma                90
_cell_volume                     811.6(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    955
_cell_measurement_temperature    205
_cell_measurement_theta_max      20.712
_cell_measurement_theta_min      2.821
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.138
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6417
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0758 before and 0.0585 after correction.
The Ratio of minimum to maximum transmission is 0.8606.
The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.646
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             416
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0535
_diffrn_reflns_av_unetI/netI     0.0552
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            6965
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.636
_diffrn_reflns_theta_min         2.439
_diffrn_ambient_temperature      205
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1326
_reflns_number_total             1869
_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 v7.68A (Bruker, 2009)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_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         0.625
_refine_diff_density_min         -0.660
_refine_diff_density_rms         0.072
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     131
_refine_ls_number_reflns         1869
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0779
_refine_ls_R_factor_gt           0.0556
_refine_ls_restrained_S_all      1.030
_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)+(0.1010P)²+0.1870P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1599
_refine_ls_wR_factor_ref         0.1751
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All N(H) groups, All N(H,H) groups
 At 1.5 times of:
  All O(H,H) groups
2.a Free rotating group:
 O2(H2A,H2B)
2.b Rotating group:
 N1(H1A,H1B)
2.c Aromatic/amide H refined with riding coordinates:
 N4(H4)
2.d X=CH2 refined with riding coordinates:
 N5(H5A,H5B)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.7028(2) 0.63726(11) 0.5466(3) 0.0309(5) Uani 1 1 d . . . . .
O2 O 0.4862(2) 0.71941(12) 0.1956(3) 0.0371(5) Uani 1 1 d . . . . .
H2A H 0.5589 0.7057 0.3124 0.056 Uiso 1 1 d G . . . .
H2B H 0.4908 0.7771 0.1712 0.056 Uiso 1 1 d G . . . .
N2 N -0.0506(2) 0.62427(12) 0.0418(3) 0.0214(5) Uani 1 1 d . . . . .
N4 N 0.1984(3) 0.65796(13) 0.1235(3) 0.0248(5) Uani 1 1 d . . . . .
H4 H 0.2878 0.6890 0.1627 0.030 Uiso 1 1 calc R . . . .
N5 N 0.0204(3) 0.78255(13) 0.1196(4) 0.0269(5) Uani 1 1 d . . . . .
H5A H 0.0953 0.8246 0.1554 0.032 Uiso 1 1 calc R . . . .
H5B H -0.0783 0.7982 0.0981 0.032 Uiso 1 1 calc R . . . .
N9 N 0.5992(3) 0.41006(13) 0.3915(4) 0.0300(5) Uani 1 1 d . . . . .
N3 N 0.1864(2) 0.56371(13) 0.0799(3) 0.0261(5) Uani 1 1 d . . . . .
N6 N 0.6847(2) 0.55095(13) 0.4786(3) 0.0243(5) Uani 1 1 d . . . . .
N1 N -0.2143(3) 0.63961(14) 0.0001(4) 0.0300(5) Uani 1 1 d . . . . .
H1A H -0.2490 0.6020 0.0739 0.036 Uiso 1 1 d GR . . . .
H1B H -0.2278 0.6960 0.0340 0.036 Uiso 1 1 d GR . . . .
N7 N 0.7914(3) 0.50900(15) 0.4090(4) 0.0357(6) Uani 1 1 d . . . . .
N8 N 0.7378(3) 0.42387(15) 0.3578(4) 0.0398(6) Uani 1 1 d . . . . .
C2 C 0.0356(3) 0.54556(14) 0.0305(4) 0.0213(5) Uani 1 1 d . . . . .
C1 C 0.0566(3) 0.69510(15) 0.0979(4) 0.0218(5) Uani 1 1 d . . . . .
C3 C 0.5663(3) 0.49029(15) 0.4673(4) 0.0224(5) Uani 1 1 d . . . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0280(11) 0.0181(8) 0.0457(12) -0.0022(7) 0.0116(9) -0.0047(7)
O2 0.0257(11) 0.0265(9) 0.0540(13) 0.0065(8) 0.0075(9) -0.0043(7)
N2 0.0174(11) 0.0166(9) 0.0299(11) 0.0009(7) 0.0079(9) 0.0004(7)
N4 0.0210(11) 0.0178(9) 0.0338(11) -0.0005(8) 0.0071(9) -0.0029(7)
N5 0.0238(12) 0.0194(10) 0.0395(13) -0.0041(8) 0.0138(10) -0.0022(8)
N9 0.0307(13) 0.0212(10) 0.0433(13) -0.0046(9) 0.0197(10) 0.0000(9)
N3 0.0240(12) 0.0185(10) 0.0339(12) 0.0017(8) 0.0076(9) -0.0007(8)
N6 0.0213(11) 0.0179(9) 0.0341(12) 0.0028(8) 0.0102(9) 0.0011(7)
N1 0.0225(12) 0.0200(10) 0.0514(14) 0.0008(9) 0.0178(10) 0.0022(8)
N7 0.0322(14) 0.0272(11) 0.0569(16) 0.0047(10) 0.0270(12) 0.0040(9)
N8 0.0410(15) 0.0274(11) 0.0632(17) 0.0017(11) 0.0333(13) 0.0044(10)
C2 0.0198(13) 0.0179(11) 0.0249(12) 0.0030(8) 0.0063(10) 0.0010(9)
C1 0.0219(13) 0.0211(11) 0.0219(12) 0.0021(8) 0.0072(9) -0.0024(9)
C3 0.0221(13) 0.0151(10) 0.0298(12) 0.0007(8) 0.0088(10) 0.0006(8)

_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 N6 1.315(2) . ?
O2 H2A 0.8501 . ?
O2 H2B 0.8501 . ?
N2 N1 1.403(3) . ?
N2 C2 1.386(3) . ?
N2 C1 1.358(3) . ?
N4 H4 0.8700 . ?
N4 N3 1.384(3) . ?
N4 C1 1.327(3) . ?
N5 H5A 0.8700 . ?
N5 H5B 0.8700 . ?
N5 C1 1.320(3) . ?
N9 N8 1.347(3) . ?
N9 C3 1.337(3) . ?
N3 C2 1.293(3) . ?
N6 N7 1.343(3) . ?
N6 C3 1.350(3) . ?
N1 H1A 0.8633 . ?
N1 H1B 0.8629 . ?
N7 N8 1.316(3) . ?
C2 C2 1.453(4) 3_565 ?
C3 C3 1.428(5) 3_666 ?

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
H2A O2 H2B 109.5 . . ?
C2 N2 N1 132.49(19) . . ?
C1 N2 N1 121.26(19) . . ?
C1 N2 C2 106.2(2) . . ?
N3 N4 H4 124.2 . . ?
C1 N4 H4 124.2 . . ?
C1 N4 N3 111.61(19) . . ?
H5A N5 H5B 120.0 . . ?
C1 N5 H5A 120.0 . . ?
C1 N5 H5B 120.0 . . ?
C3 N9 N8 105.9(2) . . ?
C2 N3 N4 104.39(19) . . ?
O1 N6 N7 122.1(2) . . ?
O1 N6 C3 129.0(2) . . ?
N7 N6 C3 108.9(2) . . ?
N2 N1 H1A 110.1 . . ?
N2 N1 H1B 109.1 . . ?
H1A N1 H1B 109.0 . . ?
N8 N7 N6 105.9(2) . . ?
N7 N8 N9 111.3(2) . . ?
N2 C2 C2 123.9(3) . 3_565 ?
N3 C2 N2 111.55(19) . . ?
N3 C2 C2 124.6(3) . 3_565 ?
N4 C1 N2 106.2(2) . . ?
N5 C1 N2 124.9(2) . . ?
N5 C1 N4 128.9(2) . . ?
N9 C3 N6 108.0(2) . . ?
N9 C3 C3 127.2(3) . 3_666 ?
N6 C3 C3 124.8(3) . 3_666 ?

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 N6 N7 N8 178.9(2) . . . . ?
O1 N6 C3 N9 -178.9(2) . . . . ?
O1 N6 C3 C3 -0.8(5) . . . 3_666 ?
N4 N3 C2 N2 -0.4(3) . . . . ?
N4 N3 C2 C2 179.2(3) . . . 3_565 ?
N3 N4 C1 N2 1.5(3) . . . . ?
N3 N4 C1 N5 -178.2(2) . . . . ?
N6 N7 N8 N9 0.4(3) . . . . ?
N1 N2 C2 N3 178.7(2) . . . . ?
N1 N2 C2 C2 -1.0(5) . . . 3_565 ?
N1 N2 C1 N4 -179.4(2) . . . . ?
N1 N2 C1 N5 0.3(4) . . . . ?
N7 N6 C3 N9 0.3(3) . . . . ?
N7 N6 C3 C3 178.4(3) . . . 3_666 ?
N8 N9 C3 N6 -0.1(3) . . . . ?
N8 N9 C3 C3 -178.2(3) . . . 3_666 ?
C2 N2 C1 N4 -1.7(3) . . . . ?
C2 N2 C1 N5 178.0(2) . . . . ?
C1 N2 C2 N3 1.4(3) . . . . ?
C1 N2 C2 C2 -178.3(3) . . . 3_565 ?
C1 N4 N3 C2 -0.7(3) . . . . ?
C3 N9 N8 N7 -0.2(3) . . . . ?
C3 N6 N7 N8 -0.4(3) . . . . ?

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