# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_xb6928
_database_code_depnum_ccdc_archive 'CCDC 948107'
_audit_update_record             
;
2013-07-01 deposited with the CCDC.	2020-09-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C6 H16 N18 O4'
_chemical_formula_weight         404.37

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                   8.4812(18)
_cell_length_b                   24.898(5)
_cell_length_c                   7.7969(16)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.961(4)
_cell_angle_gamma                90.00
_cell_volume                     1637.5(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    513
_cell_measurement_theta_min      2.92
_cell_measurement_theta_max      19.37

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.14
_exptl_crystal_density_meas      0
_exptl_crystal_density_diffrn    1.640
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             840
_exptl_absorpt_coefficient_mu    0.137
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  0.9592
_exptl_absorpt_correction_T_max  0.9808
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8206
_diffrn_reflns_av_R_equivalents  0.0737
_diffrn_reflns_av_sigmaI/netI    0.0926
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         1.64
_diffrn_reflns_theta_max         25.10
_reflns_number_total             2914
_reflns_number_gt                1515
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_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)+(0.0200P)²+0.1307P] 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         2914
_refine_ls_number_parameters     253
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1191
_refine_ls_R_factor_gt           0.0552
_refine_ls_wR_factor_ref         0.1047
_refine_ls_wR_factor_gt          0.0855
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_restrained_S_all      1.030
_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 0.7285(3) 0.41857(12) 0.5645(4) 0.0428(8) Uani 1 1 d . . .
N2 N 0.5826(3) 0.42977(10) 0.6029(3) 0.0387(7) Uani 1 1 d . . .
N3 N 0.6681(3) 0.50991(10) 0.7560(3) 0.0432(8) Uani 1 1 d . . .
H3A H 0.6449 0.5375 0.8149 0.052 Uiso 1 1 calc R . .
H3B H 0.7642 0.5048 0.7339 0.052 Uiso 1 1 calc R . .
N4 N 0.4037(3) 0.47865(10) 0.7247(3) 0.0378(7) Uani 1 1 d . . .
N5 N 0.4247(3) 0.56389(11) 0.8685(3) 0.0373(7) Uani 1 1 d . . .
N6 N 0.3493(3) 0.60277(10) 0.9418(3) 0.0382(7) Uani 1 1 d . . .
N7 N 0.1845(3) 0.51416(10) 0.8230(4) 0.0401(7) Uani 1 1 d . . .
N8 N 0.1096(3) 0.55237(10) 0.8995(4) 0.0402(7) Uani 1 1 d . . .
N9 N 0.1273(3) 0.63960(10) 1.0330(3) 0.0326(7) Uani 1 1 d . . .
N10 N -0.1268(3) 0.60202(10) 1.0399(3) 0.0484(8) Uani 1 1 d . . .
H10A H -0.1009 0.5725 0.9930 0.058 Uiso 1 1 calc R . .
H10B H -0.2214 0.6063 1.0678 0.058 Uiso 1 1 calc R . .
N11 N -0.0511(3) 0.68963(10) 1.1476(3) 0.0377(7) Uani 1 1 d . . .
N12 N -0.1938(3) 0.70133(11) 1.1846(4) 0.0414(8) Uani 1 1 d . . .
N13 N 0.9383(3) 0.84010(11) 0.1036(4) 0.0521(9) Uani 1 1 d . . .
H13A H 1.0334 0.8498 0.0895 0.062 Uiso 1 1 calc R . .
H13B H 0.9219 0.8103 0.1544 0.062 Uiso 1 1 calc R . .
N14 N 0.8411(3) 0.91645(10) -0.0299(3) 0.0490(8) Uani 1 1 d . . .
H14A H 0.9359 0.9264 -0.0445 0.059 Uiso 1 1 calc R . .
H14B H 0.7617 0.9364 -0.0662 0.059 Uiso 1 1 calc R . .
N15 N 0.6709(3) 0.85604(11) 0.0706(4) 0.0521(9) Uani 1 1 d . . .
H15A H 0.5921 0.8763 0.0347 0.063 Uiso 1 1 calc R . .
H15B H 0.6547 0.8262 0.1214 0.063 Uiso 1 1 calc R . .
N16 N 0.4679(3) 0.72020(11) 0.8590(4) 0.0534(9) Uani 1 1 d . . .
H16A H 0.5633 0.7299 0.8461 0.064 Uiso 1 1 calc R . .
H16B H 0.4503 0.6892 0.9019 0.064 Uiso 1 1 calc R . .
N17 N 0.3763(3) 0.79979(10) 0.7480(3) 0.0467(8) Uani 1 1 d . . .
H17A H 0.4720 0.8091 0.7356 0.056 Uiso 1 1 calc R . .
H17B H 0.2991 0.8213 0.7177 0.056 Uiso 1 1 calc R . .
N18 N 0.2003(3) 0.73883(10) 0.8354(4) 0.0513(9) Uani 1 1 d . . .
H18A H 0.1232 0.7606 0.8071 0.062 Uiso 1 1 calc R . .
H18B H 0.1819 0.7079 0.8782 0.062 Uiso 1 1 calc R . .
O1 O 0.8495(3) 0.44440(10) 0.6189(3) 0.0663(9) Uani 1 1 d . . .
O2 O 0.7396(3) 0.37873(10) 0.4671(3) 0.0561(7) Uani 1 1 d . . .
O3 O -0.3136(3) 0.67177(10) 1.1521(3) 0.0567(8) Uani 1 1 d . . .
O4 O -0.2100(3) 0.74624(9) 1.2581(3) 0.0511(7) Uani 1 1 d . . .
C1 C 0.5558(4) 0.47530(13) 0.6994(4) 0.0340(8) Uani 1 1 d . . .
C2 C 0.3419(4) 0.52015(13) 0.8076(4) 0.0317(8) Uani 1 1 d . . .
C3 C 0.1921(4) 0.59675(12) 0.9556(4) 0.0300(8) Uani 1 1 d . . .
C4 C -0.0214(4) 0.64065(13) 1.0689(4) 0.0332(8) Uani 1 1 d . . .
C5 C 0.8177(4) 0.87092(14) 0.0475(4) 0.0376(9) Uani 1 1 d . . .
C6 C 0.3481(4) 0.75303(14) 0.8128(4) 0.0382(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 O1 1.248(3) . ?
N1 O2 1.259(3) . ?
N1 N2 1.332(3) . ?
N2 C1 1.392(4) . ?
N3 C1 1.326(4) . ?
N3 H3A 0.8600 . ?
N3 H3B 0.8600 . ?
N4 C1 1.328(4) . ?
N4 C2 1.353(4) . ?
N5 N6 1.322(3) . ?
N5 C2 1.355(4) . ?
N6 C3 1.357(4) . ?
N7 N8 1.320(3) . ?
N7 C2 1.361(4) . ?
N8 C3 1.356(4) . ?
N9 C4 1.321(4) . ?
N9 C3 1.369(3) . ?
N10 C4 1.316(4) . ?
N10 H10A 0.8600 . ?
N10 H10B 0.8600 . ?
N11 N12 1.306(3) . ?
N11 C4 1.400(4) . ?
N12 O3 1.259(3) . ?
N12 O4 1.270(3) . ?
N13 C5 1.316(4) . ?
N13 H13A 0.8600 . ?
N13 H13B 0.8600 . ?
N14 C5 1.309(4) . ?
N14 H14A 0.8600 . ?
N14 H14B 0.8600 . ?
N15 C5 1.330(4) . ?
N15 H15A 0.8600 . ?
N15 H15B 0.8600 . ?
N16 C6 1.324(4) . ?
N16 H16A 0.8600 . ?
N16 H16B 0.8600 . ?
N17 C6 1.301(4) . ?
N17 H17A 0.8600 . ?
N17 H17B 0.8600 . ?
N18 C6 1.332(4) . ?
N18 H18A 0.8600 . ?
N18 H18B 0.8600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 N1 O2 120.1(3) . . ?
O1 N1 N2 124.5(3) . . ?
O2 N1 N2 115.4(3) . . ?
N1 N2 C1 119.9(3) . . ?
C1 N3 H3A 120.0 . . ?
C1 N3 H3B 120.0 . . ?
H3A N3 H3B 120.0 . . ?
C1 N4 C2 123.3(3) . . ?
N6 N5 C2 118.9(3) . . ?
N5 N6 C3 118.5(3) . . ?
N8 N7 C2 118.9(3) . . ?
N7 N8 C3 118.5(3) . . ?
C4 N9 C3 123.0(3) . . ?
C4 N10 H10A 120.0 . . ?
C4 N10 H10B 120.0 . . ?
H10A N10 H10B 120.0 . . ?
N12 N11 C4 120.2(3) . . ?
O3 N12 O4 118.9(3) . . ?
O3 N12 N11 124.9(3) . . ?
O4 N12 N11 116.2(3) . . ?
C5 N13 H13A 120.0 . . ?
C5 N13 H13B 120.0 . . ?
H13A N13 H13B 120.0 . . ?
C5 N14 H14A 120.0 . . ?
C5 N14 H14B 120.0 . . ?
H14A N14 H14B 120.0 . . ?
C5 N15 H15A 120.0 . . ?
C5 N15 H15B 120.0 . . ?
H15A N15 H15B 120.0 . . ?
C6 N16 H16A 120.0 . . ?
C6 N16 H16B 120.0 . . ?
H16A N16 H16B 120.0 . . ?
C6 N17 H17A 120.0 . . ?
C6 N17 H17B 120.0 . . ?
H17A N17 H17B 120.0 . . ?
C6 N18 H18A 120.0 . . ?
C6 N18 H18B 120.0 . . ?
H18A N18 H18B 120.0 . . ?
N3 C1 N4 125.8(3) . . ?
N3 C1 N2 123.9(3) . . ?
N4 C1 N2 110.3(3) . . ?
N4 C2 N5 124.7(3) . . ?
N4 C2 N7 113.0(3) . . ?
N5 C2 N7 122.3(3) . . ?
N8 C3 N6 122.9(3) . . ?
N8 C3 N9 124.1(3) . . ?
N6 C3 N9 113.0(3) . . ?
N10 C4 N9 126.5(3) . . ?
N10 C4 N11 124.2(3) . . ?
N9 C4 N11 109.2(3) . . ?
N14 C5 N13 120.6(3) . . ?
N14 C5 N15 119.5(3) . . ?
N13 C5 N15 119.9(3) . . ?
N17 C6 N16 119.4(3) . . ?
N17 C6 N18 120.1(3) . . ?
N16 C6 N18 120.4(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
O1 N1 N2 C1 5.0(5) . . . . ?
O2 N1 N2 C1 -175.4(3) . . . . ?
C2 N5 N6 C3 1.1(4) . . . . ?
C2 N7 N8 C3 1.7(4) . . . . ?
C4 N11 N12 O3 -1.3(5) . . . . ?
C4 N11 N12 O4 179.0(3) . . . . ?
C2 N4 C1 N3 2.9(5) . . . . ?
C2 N4 C1 N2 -176.9(3) . . . . ?
N1 N2 C1 N3 0.9(5) . . . . ?
N1 N2 C1 N4 -179.3(3) . . . . ?
C1 N4 C2 N5 2.6(5) . . . . ?
C1 N4 C2 N7 -178.0(3) . . . . ?
N6 N5 C2 N4 177.6(3) . . . . ?
N6 N5 C2 N7 -1.7(5) . . . . ?
N8 N7 C2 N4 -179.1(3) . . . . ?
N8 N7 C2 N5 0.3(5) . . . . ?
N7 N8 C3 N6 -2.3(5) . . . . ?
N7 N8 C3 N9 178.4(3) . . . . ?
N5 N6 C3 N8 0.9(5) . . . . ?
N5 N6 C3 N9 -179.8(3) . . . . ?
C4 N9 C3 N8 3.7(5) . . . . ?
C4 N9 C3 N6 -175.7(3) . . . . ?
C3 N9 C4 N10 1.0(5) . . . . ?
C3 N9 C4 N11 179.9(3) . . . . ?
N12 N11 C4 N10 -5.7(5) . . . . ?
N12 N11 C4 N9 175.4(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.10
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.208
_refine_diff_density_min         -0.234
_refine_diff_density_rms         0.054
####################################################################### 
# 
# 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_xb6959_0m
_database_code_depnum_ccdc_archive 'CCDC 953452'
_audit_update_record             
;
2013-07-31 deposited with the CCDC.	2020-09-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C6 H18 N20 O4'
_chemical_formula_weight         434.40

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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           Triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.4720(16)
_cell_length_b                   7.8861(16)
_cell_length_c                   8.2265(18)
_cell_angle_alpha                80.222(4)
_cell_angle_beta                 64.653(3)
_cell_angle_gamma                84.717(4)
_cell_volume                     431.61(16)
_cell_formula_units_Z            1
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    342
_cell_measurement_theta_min      3.02
_cell_measurement_theta_max      21.45

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.14
_exptl_crystal_density_meas      0
_exptl_crystal_density_diffrn    1.671
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             226
_exptl_absorpt_coefficient_mu    0.140
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  0.9506
_exptl_absorpt_correction_T_max  0.9803
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            2158
_diffrn_reflns_av_R_equivalents  0.0218
_diffrn_reflns_av_sigmaI/netI    0.0633
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         2.77
_diffrn_reflns_theta_max         25.09
_reflns_number_total             1510
_reflns_number_gt                943
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_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)+(0.0678P)²+0.6023P] 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     SHELXL
_refine_ls_extinction_coef       0.007(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         1510
_refine_ls_number_parameters     137
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1100
_refine_ls_R_factor_gt           0.0713
_refine_ls_wR_factor_ref         0.1844
_refine_ls_wR_factor_gt          0.1601
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_restrained_S_all      1.036
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.1765(5) 0.2381(5) -0.1944(5) 0.0366(9) Uani 1 1 d . . .
N2 N 0.0635(5) 0.2507(5) -0.0215(5) 0.0351(9) Uani 1 1 d . . .
N3 N 0.2925(5) 0.4317(5) 0.0008(5) 0.0431(10) Uani 1 1 d . . .
H3A H 0.3210 0.4878 0.0673 0.052 Uiso 1 1 calc R . .
H3B H 0.3718 0.4323 -0.1119 0.052 Uiso 1 1 calc R . .
N4 N -0.0069(5) 0.3351(5) 0.2447(5) 0.0344(9) Uani 1 1 d . . .
N5 N -0.1515(5) 0.3961(5) 0.5342(5) 0.0374(10) Uani 1 1 d . . .
N6 N -0.1573(5) 0.4757(5) 0.6648(5) 0.0366(9) Uani 1 1 d . . .
N7 N 0.5902(5) 0.2403(5) 0.3568(5) 0.0457(11) Uani 1 1 d . . .
H7A H 0.7082 0.2797 0.3086 0.055 Uiso 1 1 calc R . .
H7B H 0.5100 0.2577 0.4650 0.055 Uiso 1 1 calc R . .
N8 N 0.6537(5) 0.1255(5) 0.0988(5) 0.0438(11) Uani 1 1 d . . .
H8A H 0.7720 0.1643 0.0491 0.053 Uiso 1 1 calc R . .
H8B H 0.6142 0.0686 0.0402 0.053 Uiso 1 1 calc R . .
N9 N 0.3452(5) 0.0992(5) 0.3438(5) 0.0399(10) Uani 1 1 d . . .
H9 H 0.2636 0.1293 0.4462 0.048 Uiso 1 1 calc R . .
N10 N 0.2835(5) -0.0075(5) 0.2575(5) 0.0436(10) Uani 1 1 d . . .
H10A H 0.3655 -0.0374 0.1551 0.052 Uiso 1 1 calc R . .
H10B H 0.1637 -0.0428 0.3071 0.052 Uiso 1 1 calc R . .
O1 O 0.1041(5) 0.1588(4) -0.2710(4) 0.0472(9) Uani 1 1 d . . .
O2 O 0.3464(5) 0.2981(5) -0.2810(4) 0.0601(11) Uani 1 1 d . . .
C1 C 0.1266(6) 0.3448(5) 0.0718(6) 0.0307(10) Uani 1 1 d . . .
C2 C 0.0049(6) 0.4208(5) 0.3712(6) 0.0301(10) Uani 1 1 d . . .
C3 C 0.5325(6) 0.1535(6) 0.2651(6) 0.0330(10) 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 O2 1.251(4) . ?
N1 O1 1.253(4) . ?
N1 N2 1.323(4) . ?
N2 C1 1.389(5) . ?
N3 C1 1.322(5) . ?
N3 H3A 0.8600 . ?
N3 H3B 0.8600 . ?
N4 C1 1.336(5) . ?
N4 C2 1.370(5) . ?
N5 N6 1.317(4) . ?
N5 C2 1.346(5) . ?
N6 C2 1.361(5) 2_566 ?
N7 C3 1.317(5) . ?
N7 H7A 0.8600 . ?
N7 H7B 0.8600 . ?
N8 C3 1.321(5) . ?
N8 H8A 0.8600 . ?
N8 H8B 0.8600 . ?
N9 C3 1.342(5) . ?
N9 N10 1.407(5) . ?
N9 H9 0.8600 . ?
N10 H10A 0.8600 . ?
N10 H10B 0.8600 . ?
C2 N6 1.361(5) 2_566 ?

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
O2 N1 O1 119.9(4) . . ?
O2 N1 N2 124.3(4) . . ?
O1 N1 N2 115.8(3) . . ?
N1 N2 C1 119.9(3) . . ?
C1 N3 H3A 120.0 . . ?
C1 N3 H3B 120.0 . . ?
H3A N3 H3B 120.0 . . ?
C1 N4 C2 124.5(3) . . ?
N6 N5 C2 118.5(3) . . ?
N5 N6 C2 118.5(3) . 2_566 ?
C3 N7 H7A 120.0 . . ?
C3 N7 H7B 120.0 . . ?
H7A N7 H7B 120.0 . . ?
C3 N8 H8A 120.0 . . ?
C3 N8 H8B 120.0 . . ?
H8A N8 H8B 120.0 . . ?
C3 N9 N10 119.5(3) . . ?
C3 N9 H9 120.3 . . ?
N10 N9 H9 120.3 . . ?
N9 N10 H10A 120.0 . . ?
N9 N10 H10B 120.0 . . ?
H10A N10 H10B 120.0 . . ?
N3 C1 N4 125.0(4) . . ?
N3 C1 N2 125.4(4) . . ?
N4 C1 N2 109.6(3) . . ?
N5 C2 N6 123.0(4) . 2_566 ?
N5 C2 N4 113.5(3) . . ?
N6 C2 N4 123.4(4) 2_566 . ?
N7 C3 N8 120.9(4) . . ?
N7 C3 N9 117.8(4) . . ?
N8 C3 N9 121.3(4) . . ?

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
O2 N1 N2 C1 4.3(6) . . . . ?
O1 N1 N2 C1 -176.3(4) . . . . ?
C2 N5 N6 C2 0.0(6) . . . 2_566 ?
C2 N4 C1 N3 3.2(7) . . . . ?
C2 N4 C1 N2 -176.4(4) . . . . ?
N1 N2 C1 N3 2.5(6) . . . . ?
N1 N2 C1 N4 -177.9(4) . . . . ?
N6 N5 C2 N6 0.0(7) . . . 2_566 ?
N6 N5 C2 N4 -178.6(4) . . . . ?
C1 N4 C2 N5 177.4(4) . . . . ?
C1 N4 C2 N6 -1.2(7) . . . 2_566 ?
N10 N9 C3 N7 -174.1(4) . . . . ?
N10 N9 C3 N8 7.9(7) . . . . ?

_diffrn_measured_fraction_theta_max 0.984
_diffrn_reflns_theta_full        25.09
_diffrn_measured_fraction_theta_full 0.984
_refine_diff_density_max         0.403
_refine_diff_density_min         -0.359
_refine_diff_density_rms         0.068
