# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2022

####################################################################### 
# 
# 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_exp_7777
_database_code_depnum_ccdc_archive 'CCDC 2133016'
loop_
_audit_author_name
_audit_author_address
'Yong Hu'
;Beijing Institute of Technology
China
;
_audit_update_record             
;
2022-01-07 deposited with the CCDC.	2022-06-20 downloaded from the CCDC.
;
_audit_creation_date             2022-01-06
_audit_creation_method           
;
  Olex2 1.1
  (compiled 2011.02.15 svn.r1672, GUI svn.r3494)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'Mg0.5 H6 O3, C6 H3 N10 O3, 4(H2 O)'
_chemical_formula_sum            'C6 H17 Mg0.50 N10 O10'
_chemical_formula_weight         401.45
_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'
Mg Mg 0.0486 0.0363 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x, -y-1/2, z-1/2'

_cell_length_a                   9.323(2)
_cell_length_b                   26.924(6)
_cell_length_c                   6.725(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 108.46(4)
_cell_angle_gamma                90.00
_cell_volume                     1601.2(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    683
_cell_measurement_temperature    113.90(14)
_cell_measurement_theta_max      22.1520
_cell_measurement_theta_min      3.5070
_exptl_absorpt_coefficient_mu    0.171
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.32976
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.665
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             836
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0868
_diffrn_reflns_av_unetI/netI     0.1162
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_number            6285
_diffrn_reflns_theta_full        24.99
_diffrn_reflns_theta_max         24.99
_diffrn_reflns_theta_min         3.03
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      113.90(14)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0971
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.9977
_diffrn_measured_fraction_theta_max 0.8188
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   57.00   86.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       15.9289  178.0000  150.0000 29

#__ type_ start__ end____ width___ exp.time_
  2 omega  -39.00   65.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       15.9289    0.0000   60.0000 104

#__ type_ start__ end____ width___ exp.time_
  3 omega  -12.00   68.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       15.9289   19.0000  -60.0000 80
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0609444000
_diffrn_orient_matrix_UB_12      -0.0159477000
_diffrn_orient_matrix_UB_13      0.0496529000
_diffrn_orient_matrix_UB_21      -0.0360586000
_diffrn_orient_matrix_UB_22      -0.0068132000
_diffrn_orient_matrix_UB_23      0.0736656000
_diffrn_orient_matrix_UB_31      -0.0368945000
_diffrn_orient_matrix_UB_32      -0.0196856000
_diffrn_orient_matrix_UB_33      -0.0658035000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                1704
_reflns_number_total             2796
_reflns_odcompleteness_completeness 99.77
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     25.07
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'A short history of SHELX (Sheldrick, 2007)'
_refine_diff_density_max         0.721
_refine_diff_density_min         -0.539
_refine_diff_density_rms         0.103
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     283
_refine_ls_number_reflns         2796
_refine_ls_number_restraints     24
_refine_ls_R_factor_all          0.1533
_refine_ls_R_factor_gt           0.0973
_refine_ls_restrained_S_all      1.058
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1104P)²+2.3300P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2214
_refine_ls_wR_factor_ref         0.2571
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Mg1 Mg 0.5000 0.0000 -1.0000 0.0158(7) Uani 1 2 d SD . .
O6 O 0.5289(5) 0.05452(16) -0.7616(8) 0.0290(12) Uani 1 1 d D . .
N9 N 0.6779(6) -0.2670(2) -0.4275(8) 0.0262(13) Uani 1 1 d . . .
H9A H 0.5967 -0.2496 -0.4711 0.031 Uiso 1 1 calc R . .
H9B H 0.6725 -0.2989 -0.4297 0.031 Uiso 1 1 calc R . .
N7 N 0.8216(5) -0.19577(18) -0.3524(8) 0.0183(12) Uani 1 1 d . . .
O4 O 0.4680(5) -0.05762(18) -0.7955(7) 0.0324(12) Uani 1 1 d D . .
O1 O 0.6819(5) -0.07759(16) -0.4277(7) 0.0280(12) Uani 1 1 d . . .
O8 O 0.3892(5) -0.24053(17) -0.7086(8) 0.0299(12) Uani 1 1 d D . .
N8 N 0.7015(6) -0.16339(19) -0.4152(8) 0.0242(13) Uani 1 1 d . . .
H8 H 0.6071 -0.1709 -0.4623 0.029 Uiso 1 1 calc R . .
N6 N 1.0913(6) -0.19615(18) -0.2124(8) 0.0225(12) Uani 1 1 d . . .
O3 O 1.1657(5) -0.09226(16) -0.1921(8) 0.0320(12) Uani 1 1 d . . .
N3 N 0.8914(6) -0.4000(2) -0.3218(10) 0.0317(14) Uani 1 1 d . . .
N10 N 1.0291(6) -0.0819(2) -0.2580(9) 0.0261(14) Uani 1 1 d . . .
N1 N 1.0873(6) -0.35167(18) -0.2048(9) 0.0250(13) Uani 1 1 d . . .
N4 N 0.8367(6) -0.3536(2) -0.3515(9) 0.0272(14) Uani 1 1 d . . .
N5 N 1.0840(5) -0.24604(18) -0.2153(8) 0.0198(12) Uani 1 1 d . . .
N2 N 1.0387(6) -0.39878(19) -0.2369(8) 0.0252(13) Uani 1 1 d . . .
C2 C 0.9530(7) -0.2706(2) -0.2824(10) 0.0204(15) Uani 1 1 d . . .
C3 C 0.8098(7) -0.2450(2) -0.3578(10) 0.0194(14) Uani 1 1 d . . .
C4 C 0.9619(6) -0.1714(2) -0.2820(10) 0.0197(15) Uani 1 1 d . . .
O2 O 0.9828(5) -0.03835(17) -0.2796(9) 0.0438(15) Uani 1 1 d . . .
C1 C 0.9591(7) -0.3249(2) -0.2797(10) 0.0207(15) Uani 1 1 d . . .
O5 O 0.7290(5) -0.01311(16) -0.9015(8) 0.0367(13) Uani 1 1 d D . .
O9 O 1.2656(5) -0.47131(16) -0.1063(8) 0.0312(12) Uani 1 1 d D . .
O7 O 0.3937(5) -0.15791(16) -0.9447(7) 0.0304(12) Uani 1 1 d D . .
O10 O 1.3856(6) -0.3392(2) 0.1113(10) 0.0522(16) Uani 1 1 d D . .
C5 C 0.9255(7) -0.1209(2) -0.3050(10) 0.0224(15) Uani 1 1 d . . .
C6 C 0.7628(7) -0.1167(2) -0.3873(10) 0.0237(15) Uani 1 1 d . . .
H5A H 0.771(3) -0.0415(6) -0.882(11) 0.036 Uiso 1 1 d D . .
H5B H 0.797(2) 0.0090(8) -0.859(11) 0.036 Uiso 1 1 d D . .
H6A H 0.518(8) 0.0854(5) -0.789(5) 0.036 Uiso 1 1 d D . .
H6B H 0.507(8) 0.0494(11) -0.650(6) 0.036 Uiso 1 1 d D . .
H4A H 0.552(2) -0.060(2) -0.699(5) 0.036 Uiso 1 1 d D . .
H4B H 0.404(4) -0.0456(19) -0.742(7) 0.036 Uiso 1 1 d D . .
H7A H 0.423(7) -0.1288(10) -0.900(8) 0.036 Uiso 1 1 d D . .
H7B H 0.363(8) -0.1572(19) -1.0782(18) 0.036 Uiso 1 1 d D . .
H8A H 0.397(6) -0.2138(14) -0.772(10) 0.036 Uiso 1 1 d D . .
H8B H 0.304(4) -0.241(2) -0.689(11) 0.036 Uiso 1 1 d D . .
H10A H 1.385(7) -0.3105(12) 0.165(9) 0.036 Uiso 1 1 d D . .
H10B H 1.300(4) -0.344(2) 0.016(8) 0.036 Uiso 1 1 d D . .
H9C H 1.188(4) -0.4528(16) -0.139(11) 0.036 Uiso 1 1 d D . .
H9D H 1.243(6) -0.5008(9) -0.083(11) 0.036 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
Mg1 0.0143(15) 0.0133(14) 0.0203(16) -0.0001(12) 0.0064(12) 0.0008(11)
O6 0.033(3) 0.022(2) 0.038(3) 0.005(2) 0.020(2) 0.000(2)
N9 0.019(3) 0.028(3) 0.033(4) -0.002(3) 0.010(3) -0.005(2)
N7 0.015(3) 0.020(3) 0.020(3) 0.003(2) 0.006(2) 0.002(2)
O4 0.022(3) 0.038(3) 0.038(3) -0.006(2) 0.012(2) 0.005(2)
O1 0.021(2) 0.026(3) 0.038(3) 0.006(2) 0.011(2) 0.006(2)
O8 0.020(3) 0.038(3) 0.034(3) 0.003(2) 0.013(2) -0.001(2)
N8 0.012(3) 0.028(3) 0.032(3) 0.004(3) 0.007(2) 0.001(2)
N6 0.019(3) 0.021(3) 0.027(3) 0.001(2) 0.007(2) -0.002(2)
O3 0.018(3) 0.024(3) 0.051(3) 0.003(2) 0.006(2) 0.0019(19)
N3 0.027(3) 0.025(3) 0.045(4) 0.002(3) 0.014(3) -0.002(3)
N10 0.023(3) 0.026(3) 0.030(3) 0.005(3) 0.010(3) -0.001(2)
N1 0.028(3) 0.019(3) 0.031(3) 0.001(3) 0.012(3) -0.002(2)
N4 0.027(3) 0.028(3) 0.027(3) -0.001(3) 0.009(3) -0.004(3)
N5 0.012(3) 0.024(3) 0.024(3) -0.002(2) 0.006(2) 0.001(2)
N2 0.023(3) 0.022(3) 0.031(3) 0.005(2) 0.010(3) 0.003(2)
C2 0.018(3) 0.021(3) 0.024(4) -0.005(3) 0.008(3) -0.006(3)
C3 0.022(3) 0.026(4) 0.013(3) -0.001(3) 0.009(3) -0.004(3)
C4 0.008(3) 0.027(4) 0.026(4) -0.002(3) 0.009(3) -0.001(3)
O2 0.025(3) 0.022(3) 0.081(4) -0.001(3) 0.012(3) 0.001(2)
C1 0.015(3) 0.023(3) 0.027(4) 0.000(3) 0.010(3) 0.002(3)
O5 0.027(3) 0.022(3) 0.059(4) 0.000(3) 0.011(3) -0.004(2)
O9 0.019(2) 0.022(3) 0.053(3) 0.005(2) 0.012(2) 0.0032(19)
O7 0.033(3) 0.030(3) 0.027(3) -0.002(2) 0.008(2) -0.001(2)
O10 0.042(4) 0.048(3) 0.066(5) -0.008(3) 0.016(3) -0.002(3)
C5 0.021(3) 0.017(3) 0.030(4) 0.003(3) 0.009(3) -0.005(3)
C6 0.025(4) 0.024(4) 0.027(4) 0.003(3) 0.015(3) 0.002(3)

_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
Mg1 O6 2.127(5) 3_653 ?
Mg1 O6 2.127(5) . ?
Mg1 O4 2.156(5) 3_653 ?
Mg1 O4 2.156(5) . ?
Mg1 O5 2.055(5) . ?
Mg1 O5 2.055(5) 3_653 ?
O6 H6A 0.852(10) . ?
O6 H6B 0.850(10) . ?
N9 H9A 0.8600 . ?
N9 H9B 0.8600 . ?
N9 C3 1.311(8) . ?
N7 N8 1.376(7) . ?
N7 C3 1.331(8) . ?
N7 C4 1.404(7) . ?
O4 H4A 0.849(10) . ?
O4 H4B 0.854(10) . ?
O1 C6 1.274(7) . ?
O8 H8A 0.850(10) . ?
O8 H8B 0.851(10) . ?
N8 H8 0.8600 . ?
N8 C6 1.368(8) . ?
N6 N5 1.345(7) . ?
N6 C4 1.327(8) . ?
O3 N10 1.240(7) . ?
N3 N4 1.341(7) . ?
N3 N2 1.310(7) . ?
N10 O2 1.242(7) . ?
N10 C5 1.393(8) . ?
N1 N2 1.341(7) . ?
N1 C1 1.350(8) . ?
N4 C1 1.336(8) . ?
N5 C2 1.334(8) . ?
C2 C3 1.444(9) . ?
C2 C1 1.463(8) . ?
C4 C5 1.398(8) . ?
O5 H5A 0.848(10) . ?
O5 H5B 0.852(10) . ?
O9 H9C 0.849(10) . ?
O9 H9D 0.849(10) . ?
O7 H7A 0.853(10) . ?
O7 H7B 0.851(10) . ?
O10 H10A 0.854(10) . ?
O10 H10B 0.855(10) . ?
C5 C6 1.445(9) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O6 Mg1 O6 180.000(1) . 3_653 ?
O6 Mg1 O4 88.53(17) 3_653 . ?
O6 Mg1 O4 91.47(17) . . ?
O6 Mg1 O4 88.53(17) . 3_653 ?
O6 Mg1 O4 91.47(17) 3_653 3_653 ?
O4 Mg1 O4 180.000(1) 3_653 . ?
O5 Mg1 O6 89.7(2) 3_653 . ?
O5 Mg1 O6 90.3(2) . . ?
O5 Mg1 O6 89.7(2) . 3_653 ?
O5 Mg1 O6 90.3(2) 3_653 3_653 ?
O5 Mg1 O4 90.58(18) . . ?
O5 Mg1 O4 90.58(18) 3_653 3_653 ?
O5 Mg1 O4 89.42(18) . 3_653 ?
O5 Mg1 O4 89.42(18) 3_653 . ?
O5 Mg1 O5 180.0(3) 3_653 . ?
Mg1 O6 H6A 122(2) . . ?
Mg1 O6 H6B 123(2) . . ?
H6A O6 H6B 108(3) . . ?
H9A N9 H9B 120.0 . . ?
C3 N9 H9A 120.0 . . ?
C3 N9 H9B 120.0 . . ?
N8 N7 C4 112.9(4) . . ?
C3 N7 N8 124.8(5) . . ?
C3 N7 C4 122.3(5) . . ?
Mg1 O4 H4A 106(3) . . ?
Mg1 O4 H4B 105(3) . . ?
H4A O4 H4B 108(3) . . ?
H8A O8 H8B 109(3) . . ?
N7 N8 H8 127.0 . . ?
C6 N8 N7 106.0(5) . . ?
C6 N8 H8 127.0 . . ?
C4 N6 N5 117.4(5) . . ?
N2 N3 N4 109.8(5) . . ?
O3 N10 O2 122.2(5) . . ?
O3 N10 C5 118.1(5) . . ?
O2 N10 C5 119.7(5) . . ?
N2 N1 C1 103.4(5) . . ?
C1 N4 N3 104.2(5) . . ?
C2 N5 N6 122.4(5) . . ?
N3 N2 N1 110.4(5) . . ?
N5 C2 C3 121.9(5) . . ?
N5 C2 C1 117.6(5) . . ?
C3 C2 C1 120.5(5) . . ?
N9 C3 N7 121.4(6) . . ?
N9 C3 C2 124.7(6) . . ?
N7 C3 C2 113.9(5) . . ?
N6 C4 N7 122.0(5) . . ?
N6 C4 C5 133.5(5) . . ?
C5 C4 N7 104.4(5) . . ?
N1 C1 C2 124.4(5) . . ?
N4 C1 N1 112.3(5) . . ?
N4 C1 C2 123.3(5) . . ?
Mg1 O5 H5A 125.6(18) . . ?
Mg1 O5 H5B 125.4(18) . . ?
H5A O5 H5B 109(3) . . ?
H9C O9 H9D 111(3) . . ?
H7A O7 H7B 108(3) . . ?
H10A O10 H10B 108(3) . . ?
N10 C5 C4 125.6(6) . . ?
N10 C5 C6 126.6(6) . . ?
C4 C5 C6 107.8(5) . . ?
O1 C6 N8 122.5(6) . . ?
O1 C6 C5 128.6(6) . . ?
N8 C6 C5 108.9(5) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N7 N8 C6 O1 -178.9(6) . . . . ?
N7 N8 C6 C5 0.0(7) . . . . ?
N7 C4 C5 N10 -178.9(6) . . . . ?
N7 C4 C5 C6 0.6(7) . . . . ?
N8 N7 C3 N9 0.6(9) . . . . ?
N8 N7 C3 C2 -179.8(5) . . . . ?
N8 N7 C4 N6 179.2(6) . . . . ?
N8 N7 C4 C5 -0.6(7) . . . . ?
N6 N5 C2 C3 0.3(9) . . . . ?
N6 N5 C2 C1 179.6(5) . . . . ?
N6 C4 C5 N10 1.3(12) . . . . ?
N6 C4 C5 C6 -179.2(7) . . . . ?
O3 N10 C5 C4 0.8(10) . . . . ?
O3 N10 C5 C6 -178.6(6) . . . . ?
N3 N4 C1 N1 -0.6(7) . . . . ?
N3 N4 C1 C2 179.5(6) . . . . ?
N10 C5 C6 O1 -2.1(11) . . . . ?
N10 C5 C6 N8 179.1(6) . . . . ?
N4 N3 N2 N1 0.7(8) . . . . ?
N5 N6 C4 N7 1.2(9) . . . . ?
N5 N6 C4 C5 -179.0(7) . . . . ?
N5 C2 C3 N9 179.3(6) . . . . ?
N5 C2 C3 N7 -0.3(9) . . . . ?
N5 C2 C1 N1 3.3(10) . . . . ?
N5 C2 C1 N4 -176.9(6) . . . . ?
N2 N3 N4 C1 0.0(7) . . . . ?
N2 N1 C1 N4 1.0(7) . . . . ?
N2 N1 C1 C2 -179.2(6) . . . . ?
C3 N7 N8 C6 -179.1(6) . . . . ?
C3 N7 C4 N6 -1.3(9) . . . . ?
C3 N7 C4 C5 178.9(6) . . . . ?
C3 C2 C1 N1 -177.4(6) . . . . ?
C3 C2 C1 N4 2.4(10) . . . . ?
C4 N7 N8 C6 0.4(7) . . . . ?
C4 N7 C3 N9 -178.8(6) . . . . ?
C4 N7 C3 C2 0.8(8) . . . . ?
C4 N6 N5 C2 -0.8(9) . . . . ?
C4 C5 C6 O1 178.4(7) . . . . ?
C4 C5 C6 N8 -0.4(7) . . . . ?
O2 N10 C5 C4 -178.0(6) . . . . ?
O2 N10 C5 C6 2.6(10) . . . . ?
C1 N1 N2 N3 -1.0(7) . . . . ?
C1 C2 C3 N9 0.0(10) . . . . ?
C1 C2 C3 N7 -179.6(6) . . . . ?

####################################################################### 
# 
# 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_211031e
_database_code_depnum_ccdc_archive 'CCDC 2168315'
loop_
_audit_author_name
_audit_author_address
'Yong Hu'
;Beijing Institute of Technology
China
;
_audit_update_record             
;
2022-04-23 deposited with the CCDC.	2022-06-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C7 H7 N7 O3'
_chemical_formula_weight         237.20

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

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   Pnma

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

_cell_length_a                   12.8331(13)
_cell_length_b                   6.4142(7)
_cell_length_c                   12.1223(14)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     997.84(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1657
_cell_measurement_theta_min      2.311
_cell_measurement_theta_max      26.31

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.16
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.579
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             488
_exptl_absorpt_coefficient_mu    0.128
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9553
_exptl_absorpt_correction_T_max  0.9798
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'

_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            4706
_diffrn_reflns_av_R_equivalents  0.0403
_diffrn_reflns_av_sigmaI/netI    0.0333
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.31
_diffrn_reflns_theta_max         25.02
_reflns_number_total             962
_reflns_number_gt                709
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0840P)²+0.4132P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         962
_refine_ls_number_parameters     109
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0722
_refine_ls_R_factor_gt           0.0528
_refine_ls_wR_factor_ref         0.1560
_refine_ls_wR_factor_gt          0.1412
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_restrained_S_all      1.081
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 1.1514(2) 0.7500 0.7406(3) 0.0496(10) Uani 1 2 d S . .
N2 N 0.85164(19) 0.7500 0.8715(2) 0.0460(9) Uani 1 2 d S . .
H2A H 0.8010 0.7500 0.8249 0.055 Uiso 1 2 calc SR . .
H2B H 0.8389 0.7500 0.9411 0.055 Uiso 1 2 calc SR . .
N3 N 0.96706(18) 0.7500 0.7268(2) 0.0372(9) Uani 1 2 d S . .
N4 N 0.89220(19) 0.7500 0.6468(2) 0.0406(9) Uani 1 2 d S . .
N5 N 1.0551(2) 0.7500 0.5722(3) 0.0484(10) Uani 1 2 d S . .
N6 N 1.0272(3) 0.7500 1.1091(3) 0.0623(11) Uani 1 2 d S . .
N7 N 0.9050(3) 0.7500 0.4515(2) 0.0566(11) Uani 1 2 d S . .
O1 O 0.8114(2) 0.7500 0.4456(2) 0.0891(13) Uani 1 2 d S . .
O2 O 0.9635(2) 0.7500 0.3736(2) 0.0787(12) Uani 1 2 d S . .
O3 O 0.7441(3) 0.7005(17) 0.0669(3) 0.075(4) Uani 0.50 1 d P A -1
H3 H 0.6847 0.6927 0.0422 0.113 Uiso 0.50 1 calc PR A -1
C1 C 1.1356(2) 0.7500 0.8483(3) 0.0459(10) Uani 1 2 d S . .
H1 H 1.1943 0.7500 0.8933 0.055 Uiso 1 2 calc SR . .
C2 C 1.0397(2) 0.7500 0.8997(3) 0.0379(10) Uani 1 2 d S . .
C3 C 0.9474(2) 0.7500 0.8365(3) 0.0362(9) Uani 1 2 d S . .
C4 C 1.0647(2) 0.7500 0.6806(3) 0.0408(10) Uani 1 2 d S . .
C5 C 0.9516(3) 0.7500 0.5599(3) 0.0425(10) Uani 1 2 d S . .
C6 C 1.0330(2) 0.7500 1.0156(3) 0.0440(10) Uani 1 2 d S . .
C7 C 0.7400(3) 0.7500 0.1787(4) 0.0642(12) Uani 1 2 d S . .
H7A H 0.8043 0.8131 0.2016 0.096 Uiso 0.50 1 d PR A .
H7B H 0.7280 0.6256 0.2209 0.096 Uiso 0.50 1 d PR . .
H7C H 0.6837 0.8460 0.1906 0.096 Uiso 0.50 1 d PR . .

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
N1 0.0238(14) 0.072(2) 0.053(2) 0.000 0.0005(13) 0.000
N2 0.0231(13) 0.079(2) 0.0355(15) 0.000 0.0025(12) 0.000
N3 0.0243(14) 0.0501(18) 0.0373(16) 0.000 -0.0004(11) 0.000
N4 0.0271(15) 0.0586(19) 0.0360(17) 0.000 -0.0002(11) 0.000
N5 0.0284(15) 0.073(2) 0.0439(18) 0.000 0.0067(12) 0.000
N6 0.061(2) 0.079(3) 0.047(2) 0.000 -0.0024(16) 0.000
N7 0.047(2) 0.083(3) 0.0395(19) 0.000 0.0021(15) 0.000
O1 0.0388(17) 0.183(4) 0.0458(18) 0.000 -0.0062(13) 0.000
O2 0.0596(18) 0.132(3) 0.0445(18) 0.000 0.0120(14) 0.000
O3 0.0474(18) 0.128(11) 0.050(2) 0.003(3) 0.0016(14) -0.002(3)
C1 0.0275(17) 0.057(2) 0.053(2) 0.000 -0.0039(15) 0.000
C2 0.0293(17) 0.042(2) 0.043(2) 0.000 -0.0018(14) 0.000
C3 0.0275(16) 0.044(2) 0.038(2) 0.000 -0.0001(13) 0.000
C4 0.0244(16) 0.053(2) 0.045(2) 0.000 0.0040(15) 0.000
C5 0.0308(17) 0.057(2) 0.040(2) 0.000 0.0029(14) 0.000
C6 0.0319(18) 0.054(2) 0.046(2) 0.000 -0.0055(16) 0.000
C7 0.069(3) 0.072(3) 0.052(3) 0.000 0.001(2) 0.000

_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
N1 C1 1.320(5) . ?
N1 C4 1.329(4) . ?
N2 C3 1.300(4) . ?
N2 H2A 0.8600 . ?
N2 H2B 0.8600 . ?
N3 C3 1.353(4) . ?
N3 N4 1.365(3) . ?
N3 C4 1.373(4) . ?
N4 C5 1.300(4) . ?
N5 C4 1.320(5) . ?
N5 C5 1.336(4) . ?
N6 C6 1.136(5) . ?
N7 O1 1.203(4) . ?
N7 O2 1.206(4) . ?
N7 C5 1.444(5) . ?
O3 C7 1.393(6) . ?
O3 H3 0.8200 . ?
C1 C2 1.380(5) . ?
C1 H1 0.9300 . ?
C2 C6 1.408(5) . ?
C2 C3 1.411(4) . ?
C7 O3 1.393(6) 8_575 ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C4 114.4(3) . . ?
C3 N2 H2A 120.0 . . ?
C3 N2 H2B 120.0 . . ?
H2A N2 H2B 120.0 . . ?
C3 N3 N4 124.5(2) . . ?
C3 N3 C4 124.8(3) . . ?
N4 N3 C4 110.6(3) . . ?
C5 N4 N3 99.4(2) . . ?
C4 N5 C5 101.8(3) . . ?
O1 N7 O2 125.1(3) . . ?
O1 N7 C5 117.8(3) . . ?
O2 N7 C5 117.1(3) . . ?
C7 O3 H3 109.5 . . ?
N1 C1 C2 125.7(3) . . ?
N1 C1 H1 117.2 . . ?
C2 C1 H1 117.2 . . ?
C1 C2 C6 120.4(3) . . ?
C1 C2 C3 120.3(3) . . ?
C6 C2 C3 119.4(3) . . ?
N2 C3 N3 119.8(3) . . ?
N2 C3 C2 128.1(3) . . ?
N3 C3 C2 112.1(3) . . ?
N5 C4 N1 128.5(3) . . ?
N5 C4 N3 108.7(3) . . ?
N1 C4 N3 122.7(3) . . ?
N4 C5 N5 119.5(3) . . ?
N4 C5 N7 119.6(3) . . ?
N5 C5 N7 120.9(3) . . ?
N6 C6 C2 179.8(3) . . ?
O3 C7 O3 26.3(9) . 8_575 ?
O3 C7 H7A 110.1 . . ?
O3 C7 H7A 98.8 8_575 . ?
O3 C7 H7B 109.6 . . ?
O3 C7 H7B 135.6 8_575 . ?
H7A C7 H7B 109.5 . . ?
O3 C7 H7C 108.7 . . ?
O3 C7 H7C 91.6 8_575 . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C3 N3 N4 C5 180.0 . . . . ?
C4 N3 N4 C5 0.0 . . . . ?
C4 N1 C1 C2 0.000(1) . . . . ?
N1 C1 C2 C6 180.0 . . . . ?
N1 C1 C2 C3 0.000(1) . . . . ?
N4 N3 C3 N2 0.0 . . . . ?
C4 N3 C3 N2 180.0 . . . . ?
N4 N3 C3 C2 180.0 . . . . ?
C4 N3 C3 C2 0.0 . . . . ?
C1 C2 C3 N2 180.0 . . . . ?
C6 C2 C3 N2 0.000(1) . . . . ?
C1 C2 C3 N3 0.0 . . . . ?
C6 C2 C3 N3 180.0 . . . . ?
C5 N5 C4 N1 180.0 . . . . ?
C5 N5 C4 N3 0.0 . . . . ?
C1 N1 C4 N5 180.0 . . . . ?
C1 N1 C4 N3 0.0 . . . . ?
C3 N3 C4 N5 180.0 . . . . ?
N4 N3 C4 N5 0.0 . . . . ?
C3 N3 C4 N1 0.0 . . . . ?
N4 N3 C4 N1 180.0 . . . . ?
N3 N4 C5 N5 0.0 . . . . ?
N3 N4 C5 N7 180.0 . . . . ?
C4 N5 C5 N4 0.0 . . . . ?
C4 N5 C5 N7 180.0 . . . . ?
O1 N7 C5 N4 0.0 . . . . ?
O2 N7 C5 N4 180.0 . . . . ?
O1 N7 C5 N5 180.0 . . . . ?
O2 N7 C5 N5 0.0 . . . . ?
C1 C2 C6 N6 180(100) . . . . ?
C3 C2 C6 N6 0(100) . . . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        25.02
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.482
_refine_diff_density_min         -0.331
_refine_diff_density_rms         0.069
####################################################################### 
# 
# 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_210519h
_database_code_depnum_ccdc_archive 'CCDC 2168316'
loop_
_audit_author_name
_audit_author_address
'Yong Hu'
;Beijing Institute of Technology
China
;
_audit_update_record             
;
2022-04-23 deposited with the CCDC.	2022-06-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H22 N18 O10'
_chemical_formula_weight         626.52

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/m

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

_cell_length_a                   9.1828(9)
_cell_length_b                   6.5037(8)
_cell_length_c                   11.7685(13)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.504(3)
_cell_angle_gamma                90.00
_cell_volume                     699.60(13)
_cell_formula_units_Z            1
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    646
_cell_measurement_theta_min      2.692
_cell_measurement_theta_max      25.614

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.492
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             326
_exptl_absorpt_coefficient_mu    0.125
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9611
_exptl_absorpt_correction_T_max  0.9938
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            3498
_diffrn_reflns_av_R_equivalents  0.0932
_diffrn_reflns_av_sigmaI/netI    0.0727
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.23
_diffrn_reflns_theta_max         25.02
_reflns_number_total             1335
_reflns_number_gt                756
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0395P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1335
_refine_ls_number_parameters     130
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1166
_refine_ls_R_factor_gt           0.0600
_refine_ls_wR_factor_ref         0.1349
_refine_ls_wR_factor_gt          0.1185
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_restrained_S_all      1.065
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.6640(3) 0.2500 0.5667(2) 0.0710(10) Uani 1 2 d S . .
O2 O 0.1946(3) 0.2500 0.4200(2) 0.0693(10) Uani 1 2 d S . .
O3 O 0.9481(4) 0.2500 0.0197(3) 0.1188(17) Uani 1 2 d S . .
O4 O 0.7985(3) 0.2500 -0.1344(3) 0.0971(13) Uani 1 2 d S . .
O5 O 0.5690(3) 0.7500 0.2450(2) 0.0726(10) Uani 1 2 d S . .
H5C H 0.5038 0.7500 0.2916 0.109 Uiso 1 2 d SR . .
H5D H 0.5268 0.7500 0.1774 0.109 Uiso 1 2 d SR . .
N1 N 0.6345(3) 0.2500 0.3772(2) 0.0555(10) Uani 1 2 d S . .
N2 N 0.5736(4) 0.2500 0.4792(3) 0.0574(10) Uani 1 2 d S . .
N3 N 0.4312(4) 0.2500 0.4969(3) 0.0566(10) Uani 1 2 d S . .
N4 N 0.3347(3) 0.2500 0.0817(3) 0.0645(11) Uani 1 2 d S . .
N5 N 0.5602(4) 0.2500 -0.0107(2) 0.0596(11) Uani 1 2 d S . .
N6 N 0.7216(3) 0.2500 0.1512(3) 0.0574(10) Uani 1 2 d S . .
N7 N 0.5785(3) 0.2500 0.1787(2) 0.0475(9) Uani 1 2 d S . .
N8 N 0.8258(4) 0.2500 -0.0302(3) 0.0742(13) Uani 1 2 d S . .
C1 C 0.3278(5) 0.2500 0.4024(3) 0.0514(12) Uani 1 2 d S . .
C2 C 0.3786(4) 0.2500 0.2894(3) 0.0442(10) Uani 1 2 d S . .
C3 C 0.2874(4) 0.2500 0.1856(3) 0.0571(13) Uani 1 2 d S . .
H3A H 0.1868 0.2500 0.1900 0.069 Uiso 1 2 calc SR . .
C4 C 0.4818(4) 0.2500 0.0810(3) 0.0497(12) Uani 1 2 d S . .
C5 C 0.6987(4) 0.2500 0.0394(3) 0.0525(12) Uani 1 2 d S . .
C6 C 0.5312(4) 0.2500 0.2880(3) 0.0461(11) Uani 1 2 d S . .
N9 N 0.1381(3) 0.2500 0.6525(3) 0.0641(12) Uani 1 2 d S . .
H9A H 0.2241 0.2500 0.6962 0.077 Uiso 1 2 calc SR . .
H9B H 0.1573 0.2500 0.5789 0.077 Uiso 1 2 calc SR . .
C7 C 0.0559(4) 0.0626(7) 0.6758(3) 0.1043(14) Uani 1 1 d . . .
H7A H 0.0410 0.0577 0.7554 0.125 Uiso 1 1 calc R . .
H7B H 0.1103 -0.0562 0.6563 0.125 Uiso 1 1 calc R . .
H7C H -0.0372 0.0643 0.6310 0.125 Uiso 1 1 calc R . .

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 0.079(2) 0.093(3) 0.0384(16) 0.000 -0.0069(15) 0.000
O2 0.0586(19) 0.092(3) 0.0615(19) 0.000 0.0258(15) 0.000
O3 0.051(2) 0.224(5) 0.083(3) 0.000 0.0177(19) 0.000
O4 0.091(3) 0.154(4) 0.052(2) 0.000 0.0358(18) 0.000
O5 0.0672(19) 0.108(3) 0.0418(16) 0.000 0.0004(14) 0.000
N1 0.055(2) 0.080(3) 0.0320(18) 0.000 0.0058(16) 0.000
N2 0.066(3) 0.067(3) 0.038(2) 0.000 0.002(2) 0.000
N3 0.062(2) 0.070(3) 0.039(2) 0.000 0.0150(18) 0.000
N4 0.049(2) 0.101(4) 0.042(2) 0.000 0.0009(17) 0.000
N5 0.057(2) 0.087(3) 0.0354(19) 0.000 0.0078(18) 0.000
N6 0.047(2) 0.085(3) 0.041(2) 0.000 0.0112(16) 0.000
N7 0.043(2) 0.066(3) 0.0340(18) 0.000 0.0070(15) 0.000
N8 0.067(3) 0.106(4) 0.054(3) 0.000 0.026(2) 0.000
C1 0.057(3) 0.050(3) 0.049(3) 0.000 0.014(2) 0.000
C2 0.046(2) 0.046(3) 0.041(2) 0.000 0.0090(18) 0.000
C3 0.045(2) 0.077(4) 0.051(3) 0.000 0.008(2) 0.000
C4 0.054(3) 0.063(4) 0.032(2) 0.000 0.0044(19) 0.000
C5 0.059(3) 0.062(4) 0.039(2) 0.000 0.015(2) 0.000
C6 0.055(3) 0.049(3) 0.034(2) 0.000 0.0063(19) 0.000
N9 0.045(2) 0.098(4) 0.049(2) 0.000 0.0037(16) 0.000
C7 0.102(3) 0.073(3) 0.144(4) 0.027(3) 0.045(3) 0.011(2)

_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 N2 1.259(4) . ?
O2 C1 1.260(4) . ?
O3 N8 1.216(4) . ?
O4 N8 1.228(4) . ?
O5 H5C 0.8500 . ?
O5 H5D 0.8501 . ?
N1 C6 1.345(4) . ?
N1 N2 1.372(4) . ?
N2 N3 1.344(4) . ?
N3 C1 1.390(5) . ?
N4 C3 1.336(4) . ?
N4 C4 1.352(5) . ?
N5 C5 1.350(5) . ?
N5 C4 1.354(4) . ?
N6 C5 1.312(4) . ?
N6 N7 1.383(4) . ?
N7 C4 1.384(4) . ?
N7 C6 1.396(4) . ?
N8 C5 1.489(5) . ?
C1 C2 1.452(5) . ?
C2 C6 1.403(5) . ?
C2 C3 1.413(5) . ?
C3 H3A 0.9300 . ?
N9 C7 1.473(4) 4_565 ?
N9 C7 1.473(4) . ?
N9 H9A 0.9000 . ?
N9 H9B 0.9000 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
H5C O5 H5D 108.5 . . ?
C6 N1 N2 111.5(3) . . ?
O1 N2 N3 116.7(3) . . ?
O1 N2 N1 115.0(3) . . ?
N3 N2 N1 128.3(3) . . ?
N2 N3 C1 118.4(3) . . ?
C3 N4 C4 114.7(3) . . ?
C5 N5 C4 101.6(3) . . ?
C5 N6 N7 99.8(3) . . ?
C4 N7 N6 110.7(3) . . ?
C4 N7 C6 122.3(3) . . ?
N6 N7 C6 127.0(3) . . ?
O3 N8 O4 125.0(4) . . ?
O3 N8 C5 118.1(3) . . ?
O4 N8 C5 117.0(4) . . ?
O2 C1 N3 117.9(4) . . ?
O2 C1 C2 123.6(4) . . ?
N3 C1 C2 118.5(3) . . ?
C6 C2 C3 120.0(3) . . ?
C6 C2 C1 114.8(3) . . ?
C3 C2 C1 125.2(4) . . ?
N4 C3 C2 125.0(4) . . ?
N4 C3 H3A 117.5 . . ?
C2 C3 H3A 117.5 . . ?
N5 C4 N4 127.8(4) . . ?
N5 C4 N7 108.3(3) . . ?
N4 C4 N7 123.9(3) . . ?
N6 C5 N5 119.5(3) . . ?
N6 C5 N8 119.5(4) . . ?
N5 C5 N8 121.0(3) . . ?
N1 C6 N7 117.4(3) . . ?
N1 C6 C2 128.4(3) . . ?
N7 C6 C2 114.2(3) . . ?
C7 N9 C7 111.6(4) 4_565 . ?
C7 N9 H9A 109.3 4_565 . ?
C7 N9 H9A 109.3 . . ?
C7 N9 H9B 109.3 4_565 . ?
C7 N9 H9B 109.3 . . ?
H9A N9 H9B 108.0 . . ?
N9 C7 H7A 109.5 . . ?
N9 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
N9 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 N1 N2 O1 180.0 . . . . ?
C6 N1 N2 N3 0.0 . . . . ?
O1 N2 N3 C1 180.0 . . . . ?
N1 N2 N3 C1 0.0 . . . . ?
C5 N6 N7 C4 0.0 . . . . ?
C5 N6 N7 C6 180.0 . . . . ?
N2 N3 C1 O2 180.0 . . . . ?
N2 N3 C1 C2 0.0 . . . . ?
O2 C1 C2 C6 180.0 . . . . ?
N3 C1 C2 C6 0.0 . . . . ?
O2 C1 C2 C3 0.0 . . . . ?
N3 C1 C2 C3 180.0 . . . . ?
C4 N4 C3 C2 0.0 . . . . ?
C6 C2 C3 N4 0.0 . . . . ?
C1 C2 C3 N4 180.0 . . . . ?
C5 N5 C4 N4 180.0 . . . . ?
C5 N5 C4 N7 0.0 . . . . ?
C3 N4 C4 N5 180.0 . . . . ?
C3 N4 C4 N7 0.0 . . . . ?
N6 N7 C4 N5 0.0 . . . . ?
C6 N7 C4 N5 180.0 . . . . ?
N6 N7 C4 N4 180.0 . . . . ?
C6 N7 C4 N4 0.0 . . . . ?
N7 N6 C5 N5 0.0 . . . . ?
N7 N6 C5 N8 180.0 . . . . ?
C4 N5 C5 N6 0.0 . . . . ?
C4 N5 C5 N8 180.0 . . . . ?
O3 N8 C5 N6 0.0 . . . . ?
O4 N8 C5 N6 180.0 . . . . ?
O3 N8 C5 N5 180.0 . . . . ?
O4 N8 C5 N5 0.0 . . . . ?
N2 N1 C6 N7 180.0 . . . . ?
N2 N1 C6 C2 0.0 . . . . ?
C4 N7 C6 N1 180.0 . . . . ?
N6 N7 C6 N1 0.0 . . . . ?
C4 N7 C6 C2 0.0 . . . . ?
N6 N7 C6 C2 180.0 . . . . ?
C3 C2 C6 N1 180.0 . . . . ?
C1 C2 C6 N1 0.0 . . . . ?
C3 C2 C6 N7 0.0 . . . . ?
C1 C2 C6 N7 180.0 . . . . ?

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        25.02
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         0.192
_refine_diff_density_min         -0.210
_refine_diff_density_rms         0.050
####################################################################### 
# 
# 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_211031d
_database_code_depnum_ccdc_archive 'CCDC 2168314'
loop_
_audit_author_name
_audit_author_address
'Yong Hu'
;Beijing Institute of Technology
China
;
_audit_update_record             
;
2022-04-23 deposited with the CCDC.	2022-06-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C9 H11 N11 O3'
_chemical_formula_weight         321.29

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

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

_cell_length_a                   6.9809(7)
_cell_length_b                   6.8761(7)
_cell_length_c                   28.243(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 92.736(2)
_cell_angle_gamma                90.00
_cell_volume                     1354.2(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    1596
_cell_measurement_theta_min      2.872
_cell_measurement_theta_max      27.13

_exptl_crystal_description       bulk
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.576
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             664
_exptl_absorpt_coefficient_mu    0.125
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9564
_exptl_absorpt_correction_T_max  0.9901
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6274
_diffrn_reflns_av_R_equivalents  0.0838
_diffrn_reflns_av_sigmaI/netI    0.0671
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_theta_min         2.89
_diffrn_reflns_theta_max         25.01
_reflns_number_total             2371
_reflns_number_gt                1564
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0898P)²+1.0113P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2371
_refine_ls_number_parameters     210
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1203
_refine_ls_R_factor_gt           0.0861
_refine_ls_wR_factor_ref         0.2279
_refine_ls_wR_factor_gt          0.2121
_refine_ls_goodness_of_fit_ref   1.098
_refine_ls_restrained_S_all      1.098
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.2250(5) 0.1370(5) 0.76034(12) 0.0492(9) Uani 1 1 d . . .
N2 N 0.1713(4) 0.4111(5) 0.80845(10) 0.0412(8) Uani 1 1 d . . .
N3 N 0.1155(5) 0.4501(5) 0.85250(11) 0.0441(9) Uani 1 1 d . . .
N4 N 0.1241(5) 0.1235(5) 0.84005(12) 0.0482(9) Uani 1 1 d . . .
N5 N 0.2163(5) 0.7300(5) 0.78821(11) 0.0455(9) Uani 1 1 d . . .
H5A H 0.1834 0.7626 0.8161 0.055 Uiso 1 1 calc R . .
H5B H 0.2468 0.8181 0.7683 0.055 Uiso 1 1 calc R . .
N6 N 0.0274(5) 0.2454(6) 0.91558(13) 0.0521(10) Uani 1 1 d . . .
N7 N 0.3253(5) 0.7793(5) 0.69593(11) 0.0510(10) Uani 1 1 d . . .
N8 N 0.3837(5) 0.8422(6) 0.65446(12) 0.0565(10) Uani 1 1 d . . .
N9 N 0.4163(5) 0.6871(6) 0.63091(12) 0.0525(10) Uani 1 1 d . . .
H9 H 0.4563 0.6897 0.6026 0.063 Uiso 1 1 calc R . .
N10 N 0.3838(5) 0.5238(6) 0.65344(11) 0.0546(10) Uani 1 1 d . . .
N11 N 0.4961(5) 0.7584(5) 0.46894(12) 0.0498(9) Uani 1 1 d . . .
O1 O 0.0002(5) 0.3883(6) 0.93865(12) 0.0731(11) Uani 1 1 d . . .
O2 O 0.0052(6) 0.0839(6) 0.92917(12) 0.0807(12) Uani 1 1 d . . .
O3 O 0.5506(5) 0.7231(5) 0.54706(11) 0.0667(10) Uani 1 1 d . . .
C1 C 0.2704(6) 0.2641(6) 0.72783(14) 0.0444(10) Uani 1 1 d . . .
H1 H 0.3045 0.2151 0.6987 0.053 Uiso 1 1 calc R . .
C2 C 0.2720(5) 0.4645(6) 0.73316(13) 0.0383(9) Uani 1 1 d . . .
C3 C 0.2202(6) 0.5451(6) 0.77604(12) 0.0420(10) Uani 1 1 d . . .
C4 C 0.1770(6) 0.2154(6) 0.80092(13) 0.0427(10) Uani 1 1 d . . .
C5 C 0.0941(6) 0.2716(6) 0.86776(14) 0.0426(10) Uani 1 1 d . . .
C6 C 0.3267(5) 0.5888(6) 0.69421(12) 0.0402(10) Uani 1 1 d . . .
C7 C 0.4414(7) 0.7381(7) 0.51118(17) 0.0560(12) Uani 1 1 d . . .
H7 H 0.3101 0.7343 0.5154 0.067 Uiso 1 1 calc R . .
C8 C 0.6983(8) 0.7604(9) 0.45952(18) 0.0759(16) Uani 1 1 d . . .
H8A H 0.7721 0.7858 0.4884 0.114 Uiso 1 1 calc R . .
H8B H 0.7225 0.8602 0.4368 0.114 Uiso 1 1 calc R . .
H8C H 0.7344 0.6364 0.4471 0.114 Uiso 1 1 calc R . .
C9 C 0.3620(8) 0.7769(9) 0.42821(19) 0.0869(18) Uani 1 1 d . . .
H9A H 0.2334 0.7806 0.4388 0.130 Uiso 1 1 calc R . .
H9B H 0.3759 0.6676 0.4075 0.130 Uiso 1 1 calc R . .
H9C H 0.3882 0.8947 0.4115 0.130 Uiso 1 1 calc R . .

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
N1 0.065(2) 0.033(2) 0.049(2) 0.0026(16) -0.0006(16) 0.0010(18)
N2 0.051(2) 0.031(2) 0.0421(18) 0.0019(15) 0.0001(15) 0.0002(15)
N3 0.055(2) 0.037(2) 0.0403(17) 0.0002(15) 0.0002(15) 0.0016(17)
N4 0.054(2) 0.037(2) 0.053(2) 0.0012(16) -0.0047(16) -0.0024(17)
N5 0.068(2) 0.029(2) 0.0400(17) -0.0020(14) 0.0048(15) -0.0059(17)
N6 0.049(2) 0.055(3) 0.053(2) 0.004(2) 0.0030(16) -0.0021(19)
N7 0.069(3) 0.040(2) 0.0442(19) 0.0048(16) 0.0070(17) 0.0008(18)
N8 0.071(3) 0.048(3) 0.051(2) 0.0049(18) 0.0002(18) -0.005(2)
N9 0.062(2) 0.052(3) 0.0431(19) 0.0022(18) 0.0024(16) 0.0005(19)
N10 0.067(3) 0.055(3) 0.0420(19) 0.0081(18) 0.0051(17) -0.0045(19)
N11 0.064(2) 0.039(2) 0.0460(19) -0.0032(15) -0.0015(17) 0.0051(18)
O1 0.092(3) 0.065(3) 0.063(2) 0.0036(19) 0.0191(18) 0.010(2)
O2 0.108(3) 0.062(3) 0.072(2) 0.020(2) 0.0117(19) -0.020(2)
O3 0.085(2) 0.071(3) 0.0450(18) 0.0069(16) 0.0121(16) -0.0019(19)
C1 0.057(3) 0.036(3) 0.041(2) -0.0020(18) 0.0005(18) -0.001(2)
C2 0.041(2) 0.031(2) 0.042(2) -0.0012(16) -0.0026(16) 0.0051(18)
C3 0.047(2) 0.042(3) 0.0362(19) -0.0001(18) -0.0062(17) -0.002(2)
C4 0.046(2) 0.044(3) 0.038(2) -0.0002(18) -0.0038(17) -0.0022(19)
C5 0.046(2) 0.034(3) 0.048(2) 0.0010(18) -0.0049(18) 0.0002(19)
C6 0.045(2) 0.038(3) 0.037(2) 0.0018(17) -0.0054(17) -0.0016(18)
C7 0.063(3) 0.046(3) 0.060(3) -0.003(2) 0.011(2) 0.004(2)
C8 0.082(4) 0.087(4) 0.060(3) -0.002(3) 0.021(3) -0.010(3)
C9 0.100(4) 0.088(5) 0.071(3) -0.001(3) -0.023(3) 0.012(4)

_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
N1 C1 1.317(5) . ?
N1 C4 1.324(5) . ?
N2 N3 1.348(4) . ?
N2 C3 1.354(5) . ?
N2 C4 1.364(6) . ?
N3 C5 1.312(5) . ?
N4 C5 1.307(5) . ?
N4 C4 1.340(5) . ?
N5 C3 1.318(5) . ?
N5 H5A 0.8600 . ?
N5 H5B 0.8600 . ?
N6 O2 1.188(5) . ?
N6 O1 1.199(5) . ?
N6 C5 1.461(5) . ?
N7 C6 1.311(6) . ?
N7 N8 1.331(5) . ?
N8 N9 1.283(5) . ?
N9 N10 1.316(5) . ?
N9 H9 0.8600 . ?
N10 C6 1.315(5) . ?
N11 C7 1.277(6) . ?
N11 C8 1.449(6) . ?
N11 C9 1.453(6) . ?
O3 C7 1.243(6) . ?
C1 C2 1.386(6) . ?
C1 H1 0.9300 . ?
C2 C3 1.395(5) . ?
C2 C6 1.458(5) . ?
C7 H7 0.9300 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C4 114.4(4) . . ?
N3 N2 C3 125.6(3) . . ?
N3 N2 C4 110.6(3) . . ?
C3 N2 C4 123.8(3) . . ?
C5 N3 N2 99.2(3) . . ?
C5 N4 C4 100.6(4) . . ?
C3 N5 H5A 120.0 . . ?
C3 N5 H5B 120.0 . . ?
H5A N5 H5B 120.0 . . ?
O2 N6 O1 124.4(4) . . ?
O2 N6 C5 117.8(4) . . ?
O1 N6 C5 117.9(4) . . ?
C6 N7 N8 106.8(3) . . ?
N9 N8 N7 104.8(4) . . ?
N8 N9 N10 114.8(3) . . ?
N8 N9 H9 122.6 . . ?
N10 N9 H9 122.6 . . ?
C6 N10 N9 101.5(4) . . ?
C7 N11 C8 120.7(4) . . ?
C7 N11 C9 122.6(4) . . ?
C8 N11 C9 116.7(4) . . ?
N1 C1 C2 125.8(4) . . ?
N1 C1 H1 117.1 . . ?
C2 C1 H1 117.1 . . ?
C1 C2 C3 119.2(4) . . ?
C1 C2 C6 120.1(4) . . ?
C3 C2 C6 120.7(4) . . ?
N5 C3 N2 118.1(3) . . ?
N5 C3 C2 128.3(4) . . ?
N2 C3 C2 113.6(4) . . ?
N1 C4 N4 127.8(4) . . ?
N1 C4 N2 123.1(4) . . ?
N4 C4 N2 109.0(3) . . ?
N4 C5 N3 120.6(4) . . ?
N4 C5 N6 121.7(4) . . ?
N3 C5 N6 117.7(4) . . ?
N7 C6 N10 112.1(4) . . ?
N7 C6 C2 123.7(4) . . ?
N10 C6 C2 124.2(4) . . ?
O3 C7 N11 124.8(5) . . ?
O3 C7 H7 117.6 . . ?
N11 C7 H7 117.6 . . ?
N11 C8 H8A 109.5 . . ?
N11 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
N11 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N11 C9 H9A 109.5 . . ?
N11 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
N11 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C3 N2 N3 C5 -177.9(4) . . . . ?
C4 N2 N3 C5 0.5(4) . . . . ?
C6 N7 N8 N9 -0.1(5) . . . . ?
N7 N8 N9 N10 0.1(5) . . . . ?
N8 N9 N10 C6 -0.1(5) . . . . ?
C4 N1 C1 C2 0.3(6) . . . . ?
N1 C1 C2 C3 -0.6(7) . . . . ?
N1 C1 C2 C6 179.6(4) . . . . ?
N3 N2 C3 N5 1.0(6) . . . . ?
C4 N2 C3 N5 -177.2(4) . . . . ?
N3 N2 C3 C2 -179.9(3) . . . . ?
C4 N2 C3 C2 1.9(5) . . . . ?
C1 C2 C3 N5 178.5(4) . . . . ?
C6 C2 C3 N5 -1.7(6) . . . . ?
C1 C2 C3 N2 -0.5(5) . . . . ?
C6 C2 C3 N2 179.3(3) . . . . ?
C1 N1 C4 N4 179.9(4) . . . . ?
C1 N1 C4 N2 1.1(6) . . . . ?
C5 N4 C4 N1 -179.7(4) . . . . ?
C5 N4 C4 N2 -0.9(4) . . . . ?
N3 N2 C4 N1 179.2(4) . . . . ?
C3 N2 C4 N1 -2.4(6) . . . . ?
N3 N2 C4 N4 0.2(4) . . . . ?
C3 N2 C4 N4 178.7(3) . . . . ?
C4 N4 C5 N3 1.4(5) . . . . ?
C4 N4 C5 N6 178.4(3) . . . . ?
N2 N3 C5 N4 -1.2(5) . . . . ?
N2 N3 C5 N6 -178.4(3) . . . . ?
O2 N6 C5 N4 1.8(6) . . . . ?
O1 N6 C5 N4 -178.9(4) . . . . ?
O2 N6 C5 N3 178.9(4) . . . . ?
O1 N6 C5 N3 -1.7(6) . . . . ?
N8 N7 C6 N10 0.1(5) . . . . ?
N8 N7 C6 C2 179.8(4) . . . . ?
N9 N10 C6 N7 0.0(5) . . . . ?
N9 N10 C6 C2 -179.8(4) . . . . ?
C1 C2 C6 N7 177.5(4) . . . . ?
C3 C2 C6 N7 -2.3(6) . . . . ?
C1 C2 C6 N10 -2.7(6) . . . . ?
C3 C2 C6 N10 177.5(4) . . . . ?
C8 N11 C7 O3 1.6(7) . . . . ?
C9 N11 C7 O3 -179.5(5) . . . . ?

_diffrn_measured_fraction_theta_max 0.990
_diffrn_reflns_theta_full        25.01
_diffrn_measured_fraction_theta_full 0.990
_refine_diff_density_max         0.415
_refine_diff_density_min         -0.364
_refine_diff_density_rms         0.067
