# Supplementary Information (SI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2025

####################################################################### 
# 
# 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_bwn19103
_database_code_depnum_ccdc_archive 'CCDC 1939348'
loop_
_audit_author_name
_audit_author_address
'Yanna Wang'
;Beijing Institute of Technology
China
;
_audit_update_record             
;
2019-07-09 deposited with the CCDC.	2025-11-18 downloaded from the CCDC.
;
_audit_creation_date             2019-03-28
_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         'C5 H4 N10 O4, 2(H2 O), 2(H1.5 O), 2(C H8 N5)'
_chemical_formula_sum            'C7 H27 N20 O8'
_chemical_formula_weight         519.48
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   21.170(4)
_cell_length_b                   4.5087(9)
_cell_length_c                   23.576(5)
_cell_angle_alpha                90
_cell_angle_beta                 103.79(3)
_cell_angle_gamma                90
_cell_volume                     2185.5(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2968
_cell_measurement_temperature    153(2)
_cell_measurement_theta_max      27.4816
_cell_measurement_theta_min      1.7788
_shelx_estimated_absorpt_T_max   0.986
_shelx_estimated_absorpt_T_min   0.982
_exptl_absorpt_coefficient_mu    0.137
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.6732
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2008)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.579
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       rod
_exptl_crystal_F_000             1092
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0403
_diffrn_reflns_av_unetI/netI     0.0353
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            7881
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.492
_diffrn_reflns_theta_min         2.962
_diffrn_ambient_temperature      153.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'multiwire proportional'
_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                2276
_reflns_number_total             2484
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_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    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.378
_refine_diff_density_min         -0.271
_refine_diff_density_rms         0.058
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.184
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     159
_refine_ls_number_reflns         2484
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0678
_refine_ls_R_factor_gt           0.0607
_refine_ls_restrained_S_all      1.184
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0331P)²+4.3741P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1215
_refine_ls_wR_factor_ref         0.1256
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups, All N(H) groups, All N(H,H) groups, All O(H,H) groups
2. Others
 Fixed Sof: H3A(0.5) H3B(0.5) H4B(0.5)
3.a Riding coordinates:
 N4(H4), O3(H3C,H3D), O4(H4A,H4B), N8(H8A,H8B), N9(H9), N10(H10A,H10B), N6(H6A,
 H6B), N7(H7)
3.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_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 0.28037(7) 0.5797(4) 0.29080(7) 0.0275(4) Uani 1 1 d . . . . .
O2 O 0.31829(7) 0.8404(4) 0.36977(7) 0.0304(4) Uani 1 1 d . . . . .
N4 N 0.35279(8) 0.1968(4) 0.25558(7) 0.0202(4) Uani 1 1 d . . . . .
H4 H 0.312379 0.225669 0.241713 0.024 Uiso 1 1 d R . . . .
N1 N 0.32578(8) 0.6477(4) 0.33325(7) 0.0210(4) Uani 1 1 d . . . . .
N3 N 0.45341(8) 0.2076(4) 0.30728(7) 0.0197(4) Uani 1 1 d . . . . .
N2 N 0.38378(8) 0.5236(4) 0.34227(7) 0.0213(4) Uani 1 1 d . . . . .
N5 N 0.38553(8) -0.0016(4) 0.22895(7) 0.0219(4) Uani 1 1 d . . . . .
C3 C 0.500000 -0.1678(7) 0.250000 0.0221(6) Uani 1 2 d S T P . .
H3A H 0.517211 -0.297283 0.284096 0.027 Uiso 0.5 1 calc R . . . .
H3B H 0.482788 -0.297271 0.215903 0.027 Uiso 0.5 1 calc R . . . .
C1 C 0.39340(9) 0.3178(5) 0.30179(8) 0.0179(4) Uani 1 1 d . . . . .
C2 C 0.44552(9) 0.0145(5) 0.26179(9) 0.0189(4) Uani 1 1 d . . . . .
O3 O 0.20221(8) 0.1825(4) 0.36751(7) 0.0327(4) Uani 1 1 d . . . . .
H3C H 0.236042 0.096958 0.363298 0.039 Uiso 1 1 d R . . . .
H3D H 0.179362 0.258458 0.336898 0.039 Uiso 1 1 d R . . . .
O4 O 0.26724(8) 0.4946(5) 0.47404(8) 0.0446(5) Uani 1 1 d . . . . .
H4A H 0.251559 0.434348 0.439870 0.054 Uiso 1 1 d R . . . .
H4B H 0.269759 0.676998 0.467640 0.054 Uiso 0.5 1 d R . . . .
N8 N 0.37735(9) 0.7774(4) 0.58583(8) 0.0282(4) Uani 1 1 d . . . . .
H8A H 0.385602 0.956297 0.596452 0.034 Uiso 1 1 d R . . . .
H8B H 0.356382 0.701147 0.608772 0.034 Uiso 1 1 d R . . . .
N9 N 0.40054(9) 0.3766(4) 0.51169(8) 0.0254(4) Uani 1 1 d . . . . .
H9 H 0.363356 0.457828 0.506406 0.031 Uiso 1 1 d R . . . .
C4 C 0.44778(10) 0.4316(5) 0.55849(9) 0.0214(4) Uani 1 1 d . . . . .
N10 N 0.40937(9) 0.1515(4) 0.47282(8) 0.0296(4) Uani 1 1 d . . . . .
H10A H 0.398402 0.223156 0.438544 0.035 Uiso 1 1 d R . . . .
H10B H 0.384122 0.004956 0.472904 0.035 Uiso 1 1 d R . . . .
N6 N 0.50392(9) 0.2880(4) 0.56802(8) 0.0298(4) Uani 1 1 d . . . . .
H6A H 0.509723 0.162843 0.542774 0.036 Uiso 1 1 d R . . . .
H6B H 0.535473 0.338473 0.595974 0.036 Uiso 1 1 d R . . . .
N7 N 0.43781(9) 0.6287(5) 0.59767(8) 0.0285(4) Uani 1 1 d . . . . .
H7 H 0.469029 0.670221 0.626609 0.034 Uiso 1 1 d R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 N1 1.249(2) . ?
O2 N1 1.259(2) . ?
N4 N5 1.372(2) . ?
N4 C1 1.333(3) . ?
N1 N2 1.320(2) . ?
N3 C1 1.341(2) . ?
N3 C2 1.361(3) . ?
N2 C1 1.380(3) . ?
N5 C2 1.323(3) . ?
C3 C2 1.495(3) 2_655 ?
C3 C2 1.495(3) . ?
N8 N7 1.413(2) . ?
N9 C4 1.324(3) . ?
N9 N10 1.409(3) . ?
C4 N6 1.325(3) . ?
C4 N7 1.334(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
C1 N4 N5 110.07(16) . . ?
O1 N1 O2 121.24(17) . . ?
O1 N1 N2 122.26(17) . . ?
O2 N1 N2 116.50(17) . . ?
C1 N3 C2 103.04(16) . . ?
N1 N2 C1 117.28(16) . . ?
C2 N5 N4 102.45(16) . . ?
C2 C3 C2 113.3(2) 2_655 . ?
N4 C1 N3 109.80(18) . . ?
N4 C1 N2 131.87(18) . . ?
N3 C1 N2 118.33(17) . . ?
N3 C2 C3 122.90(16) . . ?
N5 C2 N3 114.64(18) . . ?
N5 C2 C3 122.45(17) . . ?
C4 N9 N10 119.06(18) . . ?
N9 C4 N6 121.2(2) . . ?
N9 C4 N7 119.28(19) . . ?
N6 C4 N7 119.44(19) . . ?
C4 N7 N8 117.70(18) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 N1 N2 C1 1.6(3) . . . . ?
O2 N1 N2 C1 -178.27(18) . . . . ?
N4 N5 C2 N3 0.1(2) . . . . ?
N4 N5 C2 C3 179.49(18) . . . . ?
N1 N2 C1 N4 -6.0(3) . . . . ?
N1 N2 C1 N3 174.40(18) . . . . ?
N5 N4 C1 N3 0.3(2) . . . . ?
N5 N4 C1 N2 -179.3(2) . . . . ?
C1 N4 N5 C2 -0.2(2) . . . . ?
C1 N3 C2 N5 0.1(2) . . . . ?
C1 N3 C2 C3 -179.33(18) . . . . ?
C2 N3 C1 N4 -0.2(2) . . . . ?
C2 N3 C1 N2 179.43(18) . . . . ?
C2 C3 C2 N3 -60.86(17) 2_655 . . . ?
C2 C3 C2 N5 119.8(2) 2_655 . . . ?
N9 C4 N7 N8 -2.2(3) . . . . ?
N10 N9 C4 N6 2.9(3) . . . . ?
N10 N9 C4 N7 -175.0(2) . . . . ?
N6 C4 N7 N8 179.9(2) . . . . ?

_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_231007d
_database_code_depnum_ccdc_archive 'CCDC 2422609'
loop_
_audit_author_name
_audit_author_address
'Xiaoming Yang'
;Beijing Institute of Technology
China
;
_audit_update_record             
;
2025-02-10 deposited with the CCDC.	2025-11-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C5 H9 N11 O5'
_chemical_formula_weight         303.23

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)/n

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

_cell_length_a                   4.2790(4)
_cell_length_b                   8.6368(8)
_cell_length_c                   30.854(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 92.692(3)
_cell_angle_gamma                90.00
_cell_volume                     1139.01(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    1587
_cell_measurement_theta_min      2.704
_cell_measurement_theta_max      27.098

_exptl_crystal_description       rodlike
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.768
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             624
_exptl_absorpt_coefficient_mu    0.155
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9364
_exptl_absorpt_correction_T_max  0.9847
_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            5358
_diffrn_reflns_av_R_equivalents  0.0978
_diffrn_reflns_av_sigmaI/netI    0.0843
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_theta_min         2.45
_diffrn_reflns_theta_max         25.02
_reflns_number_total             1961
_reflns_number_gt                1382
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_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)+(0.0882P)²+0.7447P] 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         1961
_refine_ls_number_parameters     192
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1037
_refine_ls_R_factor_gt           0.0730
_refine_ls_wR_factor_ref         0.1865
_refine_ls_wR_factor_gt          0.1705
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.048
_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 0.2603(8) 1.1477(3) 0.15207(10) 0.0315(8) Uani 1 1 d . . .
N2 N 0.4560(8) 1.0899(4) 0.18532(10) 0.0313(8) Uani 1 1 d . . .
H2 H 0.4800 1.1300 0.2108 0.038 Uiso 1 1 calc R . .
N3 N 0.5104(8) 0.9332(3) 0.13036(9) 0.0290(8) Uani 1 1 d . . .
N4 N 0.8123(8) 0.8628(4) 0.19262(9) 0.0349(8) Uani 1 1 d . . .
N5 N 0.9238(8) 0.9072(4) 0.23159(10) 0.0376(9) Uani 1 1 d . . .
N6 N 0.2321(8) 0.8569(4) 0.02050(10) 0.0321(8) Uani 1 1 d . . .
N7 N 0.1053(8) 0.7099(3) 0.01455(10) 0.0327(8) Uani 1 1 d . . .
H7 H 0.1509 0.6483 -0.0061 0.039 Uiso 1 1 calc R . .
N8 N -0.1105(7) 0.8022(3) 0.07048(9) 0.0274(7) Uani 1 1 d . . .
H8 H -0.2245 0.8134 0.0925 0.033 Uiso 1 1 calc R . .
N9 N -0.2329(8) 0.5329(3) 0.04474(10) 0.0345(8) Uani 1 1 d . . .
N10 N -0.4284(8) 0.5038(4) 0.07568(11) 0.0383(9) Uani 1 1 d . . .
N11 N 0.1551(9) 0.5379(4) 0.17734(11) 0.0463(10) Uani 1 1 d . . .
H11A H 0.0546 0.6242 0.1840 0.069 Uiso 1 1 calc R . .
H11B H 0.2870 0.5578 0.1566 0.069 Uiso 1 1 calc R . .
H11C H 0.2614 0.5026 0.2008 0.069 Uiso 1 1 calc R . .
O1 O 1.1282(7) 0.8182(3) 0.24967(9) 0.0467(8) Uani 1 1 d . . .
O2 O 0.8433(7) 1.0298(4) 0.24994(9) 0.0474(8) Uani 1 1 d . . .
O3 O -0.5074(7) 0.6066(3) 0.10186(9) 0.0429(8) Uani 1 1 d . . .
O4 O -0.5361(9) 0.3706(3) 0.07663(11) 0.0608(10) Uani 1 1 d . . .
O5 O -0.0648(8) 0.4245(4) 0.16241(12) 0.0583(9) Uani 1 1 d . . .
H5 H 0.0258 0.3423 0.1586 0.087 Uiso 1 1 calc R . .
C1 C 0.1528(10) 1.0642(4) 0.07500(11) 0.0330(10) Uani 1 1 d . . .
H1A H -0.0436 1.1194 0.0768 0.040 Uiso 1 1 calc R . .
H1B H 0.2871 1.1242 0.0569 0.040 Uiso 1 1 calc R . .
C2 C 0.3064(9) 1.0489(4) 0.11995(11) 0.0268(8) Uani 1 1 d . . .
C3 C 0.6014(9) 0.9634(4) 0.17207(11) 0.0285(9) Uani 1 1 d . . .
C4 C 0.0923(9) 0.9093(4) 0.05460(11) 0.0274(9) Uani 1 1 d . . .
C5 C -0.0961(9) 0.6761(4) 0.04495(11) 0.0286(9) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C2 1.329(5) . ?
N1 N2 1.386(4) . ?
N2 C3 1.331(5) . ?
N2 H2 0.8600 . ?
N3 C3 1.352(4) . ?
N3 C2 1.356(5) . ?
N4 N5 1.329(4) . ?
N4 C3 1.385(5) . ?
N5 O2 1.257(4) . ?
N5 O1 1.273(4) . ?
N6 C4 1.315(5) . ?
N6 N7 1.389(4) . ?
N7 C5 1.336(5) . ?
N7 H7 0.8600 . ?
N8 C5 1.347(4) . ?
N8 C4 1.375(5) . ?
N8 H8 0.8600 . ?
N9 N10 1.323(5) . ?
N9 C5 1.368(5) . ?
N10 O4 1.240(4) . ?
N10 O3 1.258(4) . ?
N11 O5 1.420(5) . ?
N11 H11A 0.8900 . ?
N11 H11B 0.8900 . ?
N11 H11C 0.8900 . ?
O5 H5 0.8200 . ?
C1 C4 1.495(5) . ?
C1 C2 1.512(5) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?

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 N1 N2 102.4(3) . . ?
C3 N2 N1 110.1(3) . . ?
C3 N2 H2 125.0 . . ?
N1 N2 H2 125.0 . . ?
C3 N3 C2 103.7(3) . . ?
N5 N4 C3 115.6(3) . . ?
O2 N5 O1 120.6(3) . . ?
O2 N5 N4 123.8(3) . . ?
O1 N5 N4 115.6(3) . . ?
C4 N6 N7 103.4(3) . . ?
C5 N7 N6 111.6(3) . . ?
C5 N7 H7 124.2 . . ?
N6 N7 H7 124.2 . . ?
C5 N8 C4 106.8(3) . . ?
C5 N8 H8 126.6 . . ?
C4 N8 H8 126.6 . . ?
N10 N9 C5 117.0(3) . . ?
O4 N10 O3 121.9(4) . . ?
O4 N10 N9 116.2(3) . . ?
O3 N10 N9 121.8(3) . . ?
O5 N11 H11A 109.5 . . ?
O5 N11 H11B 109.5 . . ?
H11A N11 H11B 109.5 . . ?
O5 N11 H11C 109.5 . . ?
H11A N11 H11C 109.5 . . ?
H11B N11 H11C 109.5 . . ?
N11 O5 H5 109.5 . . ?
C4 C1 C2 111.5(3) . . ?
C4 C1 H1A 109.3 . . ?
C2 C1 H1A 109.3 . . ?
C4 C1 H1B 109.3 . . ?
C2 C1 H1B 109.3 . . ?
H1A C1 H1B 108.0 . . ?
N1 C2 N3 114.4(3) . . ?
N1 C2 C1 123.7(3) . . ?
N3 C2 C1 121.9(3) . . ?
N2 C3 N3 109.4(3) . . ?
N2 C3 N4 132.7(3) . . ?
N3 C3 N4 117.8(3) . . ?
N6 C4 N8 111.8(3) . . ?
N6 C4 C1 124.7(3) . . ?
N8 C4 C1 123.5(3) . . ?
N7 C5 N8 106.4(3) . . ?
N7 C5 N9 119.0(3) . . ?
N8 C5 N9 134.6(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C2 N1 N2 C3 -0.6(4) . . . . ?
C3 N4 N5 O2 1.5(6) . . . . ?
C3 N4 N5 O1 -177.0(3) . . . . ?
C4 N6 N7 C5 -1.6(4) . . . . ?
C5 N9 N10 O4 -175.9(3) . . . . ?
C5 N9 N10 O3 6.1(5) . . . . ?
N2 N1 C2 N3 0.9(4) . . . . ?
N2 N1 C2 C1 -177.7(3) . . . . ?
C3 N3 C2 N1 -0.8(4) . . . . ?
C3 N3 C2 C1 177.8(3) . . . . ?
C4 C1 C2 N1 -147.9(4) . . . . ?
C4 C1 C2 N3 33.7(5) . . . . ?
N1 N2 C3 N3 0.2(4) . . . . ?
N1 N2 C3 N4 -178.7(4) . . . . ?
C2 N3 C3 N2 0.3(4) . . . . ?
C2 N3 C3 N4 179.4(3) . . . . ?
N5 N4 C3 N2 -9.1(6) . . . . ?
N5 N4 C3 N3 172.1(3) . . . . ?
N7 N6 C4 N8 0.9(4) . . . . ?
N7 N6 C4 C1 178.8(3) . . . . ?
C5 N8 C4 N6 0.1(4) . . . . ?
C5 N8 C4 C1 -177.8(3) . . . . ?
C2 C1 C4 N6 -113.1(4) . . . . ?
C2 C1 C4 N8 64.5(5) . . . . ?
N6 N7 C5 N8 1.7(4) . . . . ?
N6 N7 C5 N9 -177.5(3) . . . . ?
C4 N8 C5 N7 -1.0(4) . . . . ?
C4 N8 C5 N9 177.9(4) . . . . ?
N10 N9 C5 N7 179.3(3) . . . . ?
N10 N9 C5 N8 0.4(7) . . . . ?

_diffrn_measured_fraction_theta_max 0.980
_diffrn_reflns_theta_full        25.02
_diffrn_measured_fraction_theta_full 0.980
_refine_diff_density_max         0.314
_refine_diff_density_min         -0.364
_refine_diff_density_rms         0.078
