# 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 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_1
_database_code_depnum_ccdc_archive 'CCDC 1854906'
loop_
_audit_author_name
_audit_author_address
'Minxian Xu'
;Nanjing University of Science and Technology
China
;
_audit_update_record             
;
2019-06-04 deposited with the CCDC.	2019-06-13 downloaded from the CCDC.
;
_audit_creation_date             2019-06-03
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C7 H5 N13 O6, H2 O'
_chemical_formula_sum            'C7 H7 N13 O7'
_chemical_formula_weight         385.26
_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                   8.6518(13)
_cell_length_b                   8.7863(13)
_cell_length_c                   9.9600(14)
_cell_angle_alpha                83.380(5)
_cell_angle_beta                 66.139(5)
_cell_angle_gamma                76.502(5)
_cell_volume                     673.11(17)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1461
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      25.23
_cell_measurement_theta_min      3.17
_shelx_estimated_absorpt_T_max   0.992
_shelx_estimated_absorpt_T_min   0.985
_exptl_absorpt_coefficient_mu    0.169
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6123
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.28b (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.901
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             392
_exptl_crystal_size_max          0.09
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0812
_diffrn_reflns_av_unetI/netI     0.0966
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            5838
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        25.021
_diffrn_reflns_theta_max         25.021
_diffrn_reflns_theta_min         3.167
_diffrn_ambient_temperature      172.9
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_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                1438
_reflns_number_total             2337
_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_data_collection       crysalispro
_computing_cell_refinement       'SCALE3 ABSPACK'
_computing_data_reduction        'SCALE3 ABSPACK'
_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         0.414
_refine_diff_density_min         -0.413
_refine_diff_density_rms         0.090
_refine_ls_extinction_coef       0.019(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     263
_refine_ls_number_reflns         2337
_refine_ls_number_restraints     10
_refine_ls_R_factor_all          0.1323
_refine_ls_R_factor_gt           0.0706
_refine_ls_restrained_S_all      1.035
_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)+(0.0753P)²+1.1053P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1505
_refine_ls_wR_factor_ref         0.1850
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All N(H) groups
 At 1.5 times of:
  All O(H,H) groups
2. Restrained distances
 N4-H4 \\sim N5-H5 \\sim N1-H1 \\sim N10-H10 \\sim N11-H11
 with sigma of 0.02
3.a Free rotating group:
 O7(H7A,H7B)
;
_atom_sites_solution_hydrogens   difmap
_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
C1 C 0.2868(7) 0.0847(6) -0.0514(5) 0.0238(12) Uani 1 1 d . . . . .
C2 C 0.3224(7) 0.2333(6) -0.0472(5) 0.0214(11) Uani 1 1 d . . . . .
C3 C 0.1890(7) 0.3062(6) 0.0740(5) 0.0233(12) Uani 1 1 d . . . . .
C4 C 0.5045(6) -0.1836(5) -0.3493(5) 0.0194(11) Uani 1 1 d . . . . .
C5 C 0.3782(7) -0.0464(6) -0.1507(5) 0.0212(11) Uani 1 1 d . . . . .
C6 C 0.0479(7) 0.6378(6) 0.3035(5) 0.0234(11) Uani 1 1 d . . . . .
C7 C 0.1457(7) 0.4596(6) 0.1367(5) 0.0237(11) Uani 1 1 d . . . . .
N1 N 0.0859(6) 0.2032(5) 0.1354(5) 0.0265(10) Uani 1 1 d D . . . .
H1 H -0.021(5) 0.210(7) 0.211(5) 0.032 Uiso 1 1 d DR . . . .
N2 N 0.1409(6) 0.0680(5) 0.0614(4) 0.0271(11) Uani 1 1 d . . . . .
N3 N 0.4029(6) -0.1903(5) -0.1033(4) 0.0272(11) Uani 1 1 d . . . . .
N4 N 0.4834(6) -0.2745(5) -0.2292(4) 0.0256(10) Uani 1 1 d D . . . .
H4 H 0.500(7) -0.381(4) -0.226(6) 0.031 Uiso 1 1 d DR . . . .
N5 N 0.4366(6) -0.0355(5) -0.2989(4) 0.0227(10) Uani 1 1 d D . . . .
H5 H 0.426(7) 0.052(4) -0.356(5) 0.027 Uiso 1 1 d DR . . . .
N6 N 0.5722(5) -0.2084(4) -0.4937(4) 0.0214(9) Uani 1 1 d . . . . .
N7 N 0.6382(6) -0.3573(5) -0.5354(5) 0.0254(10) Uani 1 1 d . . . . .
N8 N 0.4769(6) 0.2857(5) -0.1418(4) 0.0241(10) Uani 1 1 d . . . . .
N9 N 0.1460(6) 0.5919(5) 0.0629(4) 0.0278(10) Uani 1 1 d . . . . .
N10 N 0.0850(6) 0.7035(5) 0.1700(4) 0.0265(10) Uani 1 1 d D . . . .
H10 H 0.077(7) 0.808(4) 0.147(6) 0.032 Uiso 1 1 d DR . . . .
N11 N 0.0880(6) 0.4817(5) 0.2844(4) 0.0234(10) Uani 1 1 d D . . . .
H11 H 0.071(7) 0.412(5) 0.363(4) 0.028 Uiso 1 1 d DR . . . .
N12 N -0.0180(6) 0.6937(5) 0.4399(5) 0.0264(10) Uani 1 1 d . . . . .
N13 N -0.0810(6) 0.8493(5) 0.4507(5) 0.0294(11) Uani 1 1 d . . . . .
O1 O 0.7032(5) -0.3798(4) -0.6687(4) 0.0293(9) Uani 1 1 d . . . . .
O2 O 0.6370(5) -0.4676(4) -0.4433(4) 0.0312(9) Uani 1 1 d . . . . .
O3 O 0.4917(5) 0.4165(4) -0.1188(4) 0.0290(9) Uani 1 1 d . . . . .
O4 O 0.5881(5) 0.1977(4) -0.2367(4) 0.0349(10) Uani 1 1 d . . . . .
O5 O -0.1506(5) 0.9017(5) 0.5772(4) 0.0380(10) Uani 1 1 d . . . . .
O6 O -0.0749(6) 0.9341(4) 0.3413(4) 0.0383(10) Uani 1 1 d . . . . .
O7 O -0.2055(6) 0.2567(5) 0.3808(4) 0.0383(10) Uani 1 1 d . . . . .
H7A H -0.244181 0.342068 0.430887 0.057 Uiso 1 1 d G . . . .
H7B H -0.188812 0.182958 0.442774 0.057 Uiso 1 1 d G . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.418(6) . ?
C1 C5 1.461(7) . ?
C1 N2 1.333(7) . ?
C2 C3 1.380(7) . ?
C2 N8 1.433(6) . ?
C3 C7 1.455(7) . ?
C3 N1 1.340(6) . ?
C4 N4 1.331(6) . ?
C4 N5 1.358(6) . ?
C4 N6 1.338(6) . ?
C5 N3 1.299(6) . ?
C5 N5 1.354(6) . ?
C6 N10 1.330(6) . ?
C6 N11 1.350(6) . ?
C6 N12 1.345(6) . ?
C7 N9 1.302(7) . ?
C7 N11 1.371(6) . ?
N1 H1 0.92(3) . ?
N1 N2 1.354(6) . ?
N3 N4 1.368(6) . ?
N4 H4 0.91(3) . ?
N5 H5 0.92(3) . ?
N6 N7 1.340(6) . ?
N7 O1 1.234(5) . ?
N7 O2 1.254(5) . ?
N8 O3 1.242(5) . ?
N8 O4 1.226(5) . ?
N9 N10 1.386(6) . ?
N10 H10 0.92(3) . ?
N11 H11 0.92(3) . ?
N12 N13 1.348(6) . ?
N13 O5 1.245(5) . ?
N13 O6 1.237(6) . ?
O7 H7A 0.8701 . ?
O7 H7B 0.8702 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C5 132.7(5) . . ?
N2 C1 C2 109.9(4) . . ?
N2 C1 C5 117.4(4) . . ?
C1 C2 N8 125.5(4) . . ?
C3 C2 C1 106.0(4) . . ?
C3 C2 N8 128.1(4) . . ?
C2 C3 C7 133.8(5) . . ?
N1 C3 C2 105.6(4) . . ?
N1 C3 C7 120.6(5) . . ?
N4 C4 N5 105.0(4) . . ?
N4 C4 N6 135.1(4) . . ?
N6 C4 N5 120.0(4) . . ?
N3 C5 C1 122.4(4) . . ?
N3 C5 N5 112.2(4) . . ?
N5 C5 C1 125.3(4) . . ?
N10 C6 N11 106.1(4) . . ?
N10 C6 N12 134.3(5) . . ?
N12 C6 N11 119.7(4) . . ?
N9 C7 C3 125.1(4) . . ?
N9 C7 N11 111.7(4) . . ?
N11 C7 C3 123.1(4) . . ?
C3 N1 H1 133(4) . . ?
C3 N1 N2 113.5(4) . . ?
N2 N1 H1 113(3) . . ?
C1 N2 N1 105.1(4) . . ?
C5 N3 N4 103.6(4) . . ?
C4 N4 N3 112.3(4) . . ?
C4 N4 H4 125(3) . . ?
N3 N4 H4 121(3) . . ?
C4 N5 H5 125(3) . . ?
C5 N5 C4 106.9(4) . . ?
C5 N5 H5 128(3) . . ?
C4 N6 N7 116.7(4) . . ?
O1 N7 N6 116.7(4) . . ?
O1 N7 O2 121.9(4) . . ?
O2 N7 N6 121.4(4) . . ?
O3 N8 C2 117.4(4) . . ?
O4 N8 C2 118.5(4) . . ?
O4 N8 O3 124.0(4) . . ?
C7 N9 N10 103.8(4) . . ?
C6 N10 N9 111.5(4) . . ?
C6 N10 H10 126(3) . . ?
N9 N10 H10 122(3) . . ?
C6 N11 C7 106.8(4) . . ?
C6 N11 H11 122(3) . . ?
C7 N11 H11 132(3) . . ?
C6 N12 N13 115.5(4) . . ?
O5 N13 N12 116.3(4) . . ?
O6 N13 N12 121.6(4) . . ?
O6 N13 O5 122.1(4) . . ?
H7A O7 H7B 104.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N1 H1 O7 0.92(3) 1.80(3) 2.698(6) 164(5) . yes
N4 H4 O3 0.91(3) 1.97(4) 2.805(5) 152(5) 1_545 yes
N5 H5 N6 0.92(3) 1.91(3) 2.810(6) 169(5) 2_654 yes
N11 H11 N12 0.92(3) 2.00(3) 2.897(6) 167(5) 2_566 yes
O7 H7A O2 0.87 2.02 2.881(5) 172.8 1_466 yes

_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_1_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1877695'
loop_
_audit_author_name
_audit_author_address
'Minxian Xu'
;Nanjing University of Science and Technology
China
;
_audit_update_record             
;
2019-06-04 deposited with the CCDC.	2019-06-13 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         'C7 H3 N11 O6, 2(H2 O)'
_chemical_formula_sum            'C7 H7 N11 O8'
_chemical_formula_weight         373.24

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

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

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

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

_cell_length_a                   5.0463(5)
_cell_length_b                   14.9379(12)
_cell_length_c                   18.6918(18)
_cell_angle_alpha                90
_cell_angle_beta                 93.903(9)
_cell_angle_gamma                90
_cell_volume                     1405.7(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    1945
_cell_measurement_theta_min      2.5830
_cell_measurement_theta_max      27.2370

_exptl_crystal_description       column
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.764
_exptl_crystal_F_000             760
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.090
_exptl_absorpt_coefficient_mu    0.159
_shelx_estimated_absorpt_T_min   0.967
_shelx_estimated_absorpt_T_max   0.986
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.73574
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.28b (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11323
_diffrn_reflns_av_unetI/netI     0.0587
_diffrn_reflns_av_R_equivalents  0.0573
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.184
_diffrn_reflns_theta_max         26.996
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3030
_reflns_number_gt                2080
_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       crysalispro
_computing_cell_refinement       'SCALE3 ABSPACK'
_computing_data_reduction        'SCALE3 ABSPACK'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0439P)²+0.7645P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3030
_refine_ls_number_parameters     256
_refine_ls_number_restraints     7
_refine_ls_R_factor_all          0.0806
_refine_ls_R_factor_gt           0.0486
_refine_ls_wR_factor_ref         0.1280
_refine_ls_wR_factor_gt          0.1127
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_restrained_S_all      1.053
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.4138(4) 0.43541(14) 0.89023(11) 0.0291(5) Uani 1 1 d . . . . .
C2 C 0.2895(4) 0.35415(15) 0.90692(11) 0.0291(5) Uani 1 1 d . . . . .
C3 C 0.4393(4) 0.31806(14) 0.96536(11) 0.0284(5) Uani 1 1 d . . . . .
C4 C 0.4278(5) 0.61083(16) 0.76829(13) 0.0370(5) Uani 1 1 d . . . . .
C5 C 0.3721(4) 0.50170(15) 0.83301(11) 0.0311(5) Uani 1 1 d . . . . .
C6 C 0.5731(5) 0.14183(16) 1.08277(12) 0.0349(5) Uani 1 1 d . . . . .
C7 C 0.4451(4) 0.23563(14) 1.00742(12) 0.0308(5) Uani 1 1 d . . . . .
N1 N 0.6313(4) 0.37829(12) 0.98073(10) 0.0317(4) Uani 1 1 d D . . . .
H1 H 0.761(4) 0.3757(16) 1.0146(12) 0.038 Uiso 1 1 d D U . . .
N2 N 0.6232(4) 0.44900(12) 0.93634(10) 0.0333(4) Uani 1 1 d . . . . .
N3 N 0.1939(4) 0.50061(14) 0.77698(11) 0.0391(5) Uani 1 1 d D . . . .
H3 H 0.079(5) 0.4600(16) 0.7652(14) 0.047 Uiso 1 1 d D U . . .
N4 N 0.2268(4) 0.57151(14) 0.73351(11) 0.0432(5) Uani 1 1 d . . . . .
N5 N 0.5271(4) 0.57349(13) 0.82907(10) 0.0354(5) Uani 1 1 d . . . . .
N6 N 0.5451(4) 0.69023(15) 0.73875(12) 0.0498(6) Uani 1 1 d . . . . .
N7 N 0.0567(4) 0.31581(13) 0.87282(10) 0.0351(5) Uani 1 1 d . . . . .
N8 N 0.2881(4) 0.16322(13) 1.00097(10) 0.0353(5) Uani 1 1 d D . . . .
H8 H 0.153(4) 0.1508(17) 0.9724(12) 0.042 Uiso 1 1 d D U . . .
N9 N 0.3693(4) 0.10142(13) 1.05008(10) 0.0378(5) Uani 1 1 d . . . . .
N10 N 0.6325(4) 0.22356(13) 1.06007(10) 0.0346(5) Uani 1 1 d . . . . .
N11 N 0.7276(4) 0.09937(14) 1.14200(12) 0.0445(5) Uani 1 1 d . . . . .
O1 O 0.5295(4) 0.69713(14) 0.67381(11) 0.0634(6) Uani 1 1 d . . . . .
O2 O 0.6552(5) 0.74264(17) 0.78041(13) 0.0855(8) Uani 1 1 d . . . . .
O3 O -0.0556(3) 0.35334(12) 0.82081(9) 0.0430(4) Uani 1 1 d . . . . .
O4 O -0.0252(3) 0.24670(13) 0.89834(11) 0.0552(5) Uani 1 1 d . . . . .
O5 O 0.6439(4) 0.02986(15) 1.16564(12) 0.0718(7) Uani 1 1 d . . . . .
O6 O 0.9313(4) 0.13585(13) 1.16440(10) 0.0564(5) Uani 1 1 d . . . . .
O7 O 0.9805(4) 0.63618(14) 0.91368(11) 0.0518(5) Uani 1 1 d D . . . .
H7A H 0.844(5) 0.6118(19) 0.8930(15) 0.062 Uiso 1 1 d D U . . .
H7B H 1.009(6) 0.6806(16) 0.8891(15) 0.062 Uiso 1 1 d D U . . .
O8 O 0.1291(5) 0.92488(15) 0.06688(11) 0.0706(7) Uani 1 1 d D . . . .
H8A H 0.163(7) 0.917(3) 0.1094(11) 0.085 Uiso 1 1 d D U . . .
H8B H 0.181(7) 0.9744(15) 0.0604(18) 0.085 Uiso 1 1 d D U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N2 1.333(3) . ?
C1 C2 1.411(3) . ?
C1 C5 1.462(3) . ?
C2 C3 1.394(3) . ?
C2 N7 1.418(3) . ?
C3 N1 1.339(3) . ?
C3 C7 1.460(3) . ?
C4 N4 1.306(3) . ?
C4 N5 1.332(3) . ?
C4 N6 1.451(3) . ?
C5 N5 1.332(3) . ?
C5 N3 1.333(3) . ?
C6 N9 1.307(3) . ?
C6 N10 1.333(3) . ?
C6 N11 1.456(3) . ?
C7 N10 1.330(3) . ?
C7 N8 1.342(3) . ?
N1 N2 1.342(3) . ?
N1 H1 0.88(2) . ?
N3 N4 1.352(3) . ?
N3 H3 0.86(2) . ?
N6 O2 1.212(3) . ?
N6 O1 1.215(3) . ?
N7 O4 1.221(3) . ?
N7 O3 1.227(2) . ?
N8 N9 1.346(3) . ?
N8 H8 0.86(2) . ?
N11 O6 1.213(3) . ?
N11 O5 1.215(3) . ?
O7 H7A 0.850(18) . ?
O7 H7B 0.825(18) . ?
O8 H8A 0.812(18) . ?
O8 H8B 0.797(19) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 C1 C2 109.45(19) . . ?
N2 C1 C5 115.97(19) . . ?
C2 C1 C5 134.5(2) . . ?
C3 C2 C1 106.29(19) . . ?
C3 C2 N7 125.8(2) . . ?
C1 C2 N7 127.9(2) . . ?
N1 C3 C2 104.72(19) . . ?
N1 C3 C7 117.61(19) . . ?
C2 C3 C7 137.6(2) . . ?
N4 C4 N5 118.0(2) . . ?
N4 C4 N6 120.1(2) . . ?
N5 C4 N6 121.8(2) . . ?
N5 C5 N3 109.5(2) . . ?
N5 C5 C1 122.00(19) . . ?
N3 C5 C1 128.5(2) . . ?
N9 C6 N10 117.4(2) . . ?
N9 C6 N11 121.2(2) . . ?
N10 C6 N11 121.4(2) . . ?
N10 C7 N8 110.07(19) . . ?
N10 C7 C3 120.0(2) . . ?
N8 C7 C3 129.9(2) . . ?
C3 N1 N2 113.91(18) . . ?
C3 N1 H1 128.1(17) . . ?
N2 N1 H1 118.0(17) . . ?
C1 N2 N1 105.61(18) . . ?
C5 N3 N4 111.0(2) . . ?
C5 N3 H3 128.2(19) . . ?
N4 N3 H3 120.6(19) . . ?
C4 N4 N3 100.16(18) . . ?
C5 N5 C4 101.31(18) . . ?
O2 N6 O1 125.6(2) . . ?
O2 N6 C4 117.7(2) . . ?
O1 N6 C4 116.7(2) . . ?
O4 N7 O3 123.05(19) . . ?
O4 N7 C2 117.2(2) . . ?
O3 N7 C2 119.69(19) . . ?
C7 N8 N9 109.93(19) . . ?
C7 N8 H8 132.1(18) . . ?
N9 N8 H8 117.9(18) . . ?
C6 N9 N8 101.28(18) . . ?
C7 N10 C6 101.28(19) . . ?
O6 N11 O5 124.5(2) . . ?
O6 N11 C6 117.7(2) . . ?
O5 N11 C6 117.9(2) . . ?
H7A O7 H7B 105(3) . . ?
H8A O8 H8B 104(4) . . ?

_refine_diff_density_max         0.314
_refine_diff_density_min         -0.299
_refine_diff_density_rms         0.059

