# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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 1816435'
_audit_update_record             
;
2018-01-11 deposited with the CCDC.
2018-03-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 H2 N3 O7, C7 H16 N'
_chemical_formula_sum            'C13 H18 N4 O7'
_chemical_formula_weight         342.31

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_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+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   6.67620(10)
_cell_length_b                   12.7767(2)
_cell_length_c                   18.3011(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1561.08(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    205(2)
_cell_measurement_reflns_used    3515
_cell_measurement_theta_min      4.8110
_cell_measurement_theta_max      73.0730
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.456
_exptl_crystal_F_000             720
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    1.025
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      205(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4847
_diffrn_reflns_av_unetI/netI     0.0188
_diffrn_reflns_av_R_equivalents  0.0137
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         4.833
_diffrn_reflns_theta_max         66.551
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.969
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.969
_diffrn_reflns_point_group_measured_fraction_max 0.923
_diffrn_reflns_point_group_measured_fraction_full 0.901
_reflns_number_total             2533
_reflns_number_gt                2398
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.592
_reflns_Friedel_fraction_max     0.827
_reflns_Friedel_fraction_full    0.807

_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0573P)²+0.1034P]
 where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 876 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.41(9)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2533
_refine_ls_number_parameters     218
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0338
_refine_ls_R_factor_gt           0.0319
_refine_ls_wR_factor_ref         0.0857
_refine_ls_wR_factor_gt          0.0842
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_restrained_S_all      1.045
_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
O1 O 0.2394(3) 0.27910(12) 0.64374(7) 0.0374(4) Uani 1 1 d . . . . .
C3 C 0.2300(3) 0.11865(15) 0.48007(11) 0.0271(4) Uani 1 1 d . . . . .
H3 H 0.2322 0.0474 0.4672 0.033 Uiso 1 1 calc R U . . .
O5 O 0.2484(3) 0.23799(14) 0.30498(8) 0.0506(5) Uani 1 1 d . . . . .
C6 C 0.2276(3) 0.32876(15) 0.51770(10) 0.0255(4) Uani 1 1 d . . . . .
C5 C 0.2329(3) 0.30109(16) 0.44547(11) 0.0269(4) Uani 1 1 d . . . . .
H5 H 0.2372 0.3528 0.4090 0.032 Uiso 1 1 calc R U . . .
N3 N 0.2267(3) 0.44049(14) 0.53320(9) 0.0320(4) Uani 1 1 d . . . . .
C1 C 0.2265(3) 0.25562(15) 0.57783(10) 0.0250(4) Uani 1 1 d . . . . .
O4 O 0.2365(3) 0.07497(14) 0.33368(9) 0.0513(5) Uani 1 1 d . . . . .
C4 C 0.2320(3) 0.19598(16) 0.42678(10) 0.0273(4) Uani 1 1 d . . . . .
N2 N 0.2378(3) 0.16809(15) 0.35038(10) 0.0351(4) Uani 1 1 d . . . . .
N1 N 0.2215(3) 0.06542(15) 0.60633(10) 0.0380(4) Uani 1 1 d . . . . .
O2 O 0.1072(3) 0.07342(15) 0.65814(9) 0.0523(5) Uani 1 1 d . . . . .
O6 O 0.3131(3) 0.49946(13) 0.49050(10) 0.0494(5) Uani 1 1 d . . . . .
O7 O 0.1368(3) 0.47076(13) 0.58742(10) 0.0519(5) Uani 1 1 d . . . . .
O3 O 0.3292(5) -0.00962(18) 0.59621(13) 0.0841(8) Uani 1 1 d . . . . .
N4 N 0.1597(3) 0.42387(15) 0.75269(9) 0.0358(4) Uani 1 1 d . . . . .
H4A H 0.1807 0.3768 0.7111 0.043 Uiso 1 1 calc R U . . .
H4B H 0.0183 0.4444 0.7528 0.043 Uiso 1 1 calc R U . . .
C8 C 0.2040(3) 0.36499(17) 0.82229(10) 0.0319(5) Uani 1 1 d . . . . .
H8 H 0.2111 0.4162 0.8628 0.038 Uiso 1 1 calc R U . . .
C13 C 0.4029(4) 0.3091(2) 0.81769(13) 0.0414(6) Uani 1 1 d . . . . .
H13A H 0.5098 0.3597 0.8078 0.050 Uiso 1 1 calc R U . . .
H13B H 0.4001 0.2582 0.7777 0.050 Uiso 1 1 calc R U . . .
C9 C 0.0349(4) 0.2895(2) 0.83833(14) 0.0452(6) Uani 1 1 d . . . . .
H9A H 0.0255 0.2375 0.7992 0.054 Uiso 1 1 calc R U . . .
H9B H -0.0923 0.3276 0.8406 0.054 Uiso 1 1 calc R U . . .
C7 C 0.2846(5) 0.51900(19) 0.74213(13) 0.0482(6) Uani 1 1 d . . . . .
H7A H 0.2738 0.5636 0.7849 0.072 Uiso 1 1 calc R U . . .
H7B H 0.2382 0.5568 0.6994 0.072 Uiso 1 1 calc R U . . .
H7C H 0.4233 0.4987 0.7352 0.072 Uiso 1 1 calc R U . . .
C10 C 0.0741(5) 0.2350(2) 0.91093(17) 0.0556(7) Uani 1 1 d . . . . .
H10A H -0.0329 0.1843 0.9205 0.067 Uiso 1 1 calc R U . . .
H10B H 0.0729 0.2868 0.9504 0.067 Uiso 1 1 calc R U . . .
C11 C 0.2753(5) 0.1788(2) 0.91020(16) 0.0586(8) Uani 1 1 d . . . . .
H11A H 0.3016 0.1491 0.9586 0.070 Uiso 1 1 calc R U . . .
H11B H 0.2706 0.1210 0.8750 0.070 Uiso 1 1 calc R U . . .
C12 C 0.4439(4) 0.2531(2) 0.88975(16) 0.0536(7) Uani 1 1 d . . . . .
H12A H 0.5693 0.2137 0.8857 0.064 Uiso 1 1 calc R U . . .
H12B H 0.4604 0.3052 0.9286 0.064 Uiso 1 1 calc R U . . .
C2 C 0.2247(3) 0.14861(15) 0.55173(11) 0.0265(4) 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
O1 C1 1.246(2) . ?
C3 C2 1.367(3) . ?
C3 C4 1.388(3) . ?
O5 N2 1.222(2) . ?
C6 C5 1.369(3) . ?
C6 C1 1.444(3) . ?
C6 N3 1.456(3) . ?
C5 C4 1.386(3) . ?
N3 O7 1.222(3) . ?
N3 O6 1.229(3) . ?
C1 C2 1.448(3) . ?
O4 N2 1.229(3) . ?
C4 N2 1.443(2) . ?
N1 O3 1.213(3) . ?
N1 O2 1.221(3) . ?
N1 C2 1.459(3) . ?
N4 C7 1.487(3) . ?
N4 C8 1.509(3) . ?
C8 C13 1.510(3) . ?
C8 C9 1.513(3) . ?
C13 C12 1.525(4) . ?
C9 C10 1.523(4) . ?
C10 C11 1.523(5) . ?
C11 C12 1.520(4) . ?

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 C3 C4 118.36(18) . . ?
C5 C6 C1 124.69(18) . . ?
C5 C6 N3 116.21(17) . . ?
C1 C6 N3 119.09(17) . . ?
C6 C5 C4 119.25(18) . . ?
O7 N3 O6 123.54(19) . . ?
O7 N3 C6 118.07(18) . . ?
O6 N3 C6 118.38(17) . . ?
O1 C1 C6 125.58(18) . . ?
O1 C1 C2 123.17(18) . . ?
C6 C1 C2 111.08(16) . . ?
C5 C4 C3 121.08(17) . . ?
C5 C4 N2 118.57(18) . . ?
C3 C4 N2 120.34(18) . . ?
O5 N2 O4 122.63(18) . . ?
O5 N2 C4 118.67(18) . . ?
O4 N2 C4 118.68(18) . . ?
O3 N1 O2 123.7(2) . . ?
O3 N1 C2 117.57(19) . . ?
O2 N1 C2 118.68(18) . . ?
C7 N4 C8 114.06(18) . . ?
N4 C8 C13 111.16(17) . . ?
N4 C8 C9 109.60(19) . . ?
C13 C8 C9 111.43(19) . . ?
C8 C13 C12 109.4(2) . . ?
C8 C9 C10 109.4(2) . . ?
C9 C10 C11 111.1(2) . . ?
C12 C11 C10 111.1(2) . . ?
C11 C12 C13 111.9(2) . . ?
C3 C2 C1 125.50(18) . . ?
C3 C2 N1 116.97(17) . . ?
C1 C2 N1 117.51(17) . . ?

_refine_diff_density_max         0.240
_refine_diff_density_min         -0.161
_refine_diff_density_rms         0.038

_shelxl_version_number           2013-2



####################################################################### 
# 
# 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_x
_database_code_depnum_ccdc_archive 'CCDC 1816476'
_audit_update_record             
;
2018-01-12 deposited with the CCDC.
2018-03-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 H2 N3 O7, C7 H16 N'
_chemical_formula_sum            'C13 H18 N4 O7'
_chemical_formula_weight         342.31

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           62
_space_group_name_H-M_alt        'P n m a'
_space_group_name_Hall           '-P 2ac 2n'

_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+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                   18.2587(3)
_cell_length_b                   6.7913(2)
_cell_length_c                   12.8788(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1596.98(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2308
_cell_measurement_theta_min      4.1720
_cell_measurement_theta_max      72.7700
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.424
_exptl_crystal_F_000             720
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    1.002
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4977
_diffrn_reflns_av_unetI/netI     0.0191
_diffrn_reflns_av_R_equivalents  0.0160
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         4.201
_diffrn_reflns_theta_max         73.194
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.962
_diffrn_measured_fraction_theta_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.962
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.962
_diffrn_reflns_point_group_measured_fraction_full 0.990
_reflns_number_total             1672
_reflns_number_gt                1379
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0100P)²+1.3200P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_extinction_coef       0.00281(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         1672
_refine_ls_number_parameters     162
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0728
_refine_ls_R_factor_gt           0.0621
_refine_ls_wR_factor_ref         0.1076
_refine_ls_wR_factor_gt          0.1029
_refine_ls_goodness_of_fit_ref   1.008
_refine_ls_restrained_S_all      1.011
_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
O1 O 0.35521(11) 0.250000 0.02940(19) 0.0828(8) Uani 1 2 d S T P . .
O2 O 0.3371(2) 0.3726(8) -0.1727(3) 0.1238(19) Uani 0.5 1 d . . P . .
O3 O 0.3998(3) 0.1676(11) -0.2589(4) 0.175(4) Uani 0.5 1 d . . P . .
O4 O 0.69321(14) 0.250000 -0.0193(3) 0.1120(12) Uani 1 2 d S T P . .
O5 O 0.66221(15) 0.250000 -0.1787(3) 0.1234(13) Uani 1 2 d S T P . .
O6 O 0.41083(19) 0.1703(7) 0.2178(2) 0.106(2) Uani 0.5 1 d . . P . .
O7 O 0.5149(2) 0.1840(7) 0.2438(3) 0.101(2) Uani 0.5 1 d . . P . .
N1 N 0.3891(2) 0.250000 -0.1822(3) 0.0959(12) Uani 1 2 d S T P . .
N2 N 0.64693(16) 0.250000 -0.0875(3) 0.0824(9) Uani 1 2 d S T P . .
N3 N 0.46786(17) 0.250000 0.1869(2) 0.0759(9) Uani 1 2 d S T P . .
C1 C 0.42064(15) 0.250000 0.0045(2) 0.0560(8) Uani 1 2 d S T P . .
C2 C 0.44521(16) 0.250000 -0.1017(2) 0.0597(8) Uani 1 2 d S T P . .
C3 C 0.51648(17) 0.250000 -0.1322(3) 0.0616(8) Uani 1 2 d S T P . .
H3 H 0.528500 0.250000 -0.202379 0.074 Uiso 1 2 calc R U P . .
C4 C 0.57065(16) 0.250000 -0.0578(3) 0.0598(8) Uani 1 2 d S T P . .
C5 C 0.55335(16) 0.250000 0.0455(3) 0.0588(8) Uani 1 2 d S T P . .
H5 H 0.590346 0.250000 0.095129 0.071 Uiso 1 2 calc R U P . .
C6 C 0.48165(16) 0.250000 0.0757(2) 0.0558(7) Uani 1 2 d S T P . .
N4 N 0.2440(2) 0.1611(7) 0.1685(3) 0.0793(14) Uani 0.5 1 d D . P . .
H4A H 0.2765(16) 0.250000 0.140(2) 0.095 Uiso 1 2 d DS U P . .
H4B H 0.259(2) 0.043(3) 0.197(3) 0.095 Uiso 0.5 1 d D U P . .
C7 C 0.2524(2) 0.250000 0.2692(3) 0.132(2) Uani 1 2 d DS T P . .
H7A H 0.299298 0.284900 0.297517 0.197 Uiso 0.5 1 calc R U P . .
H7B H 0.249153 0.109436 0.262850 0.197 Uiso 0.5 1 calc R U P . .
H7C H 0.214389 0.296364 0.314537 0.197 Uiso 0.5 1 calc R U P . .
C8 C 0.17608(18) 0.250000 0.1083(3) 0.0909(15) Uani 1 2 d S T P . .
H8 H 0.135792 0.250000 0.158843 0.084(11) Uiso 1 2 d R . P . .
C9 C 0.1725(2) 0.0733(6) 0.0453(3) 0.1341(15) Uani 1 1 d . . . . .
H9A H 0.175717 -0.042611 0.089028 0.161 Uiso 1 1 calc DR U . . .
H9B H 0.212958 0.070713 -0.003566 0.161 Uiso 1 1 calc R U . . .
C10 C 0.1015(3) 0.0748(11) -0.0117(4) 0.214(4) Uani 1 1 d . . . . .
H10A H 0.098140 -0.041456 -0.055184 0.257 Uiso 1 1 calc R U . . .
H10B H 0.061411 0.071127 0.037720 0.257 Uiso 1 1 calc R U . . .
C11 C 0.0953(5) 0.250000 -0.0756(5) 0.256(10) Uani 1 2 d S T P . .
H11A H 0.048467 0.249999 -0.111125 0.307 Uiso 1 2 calc R U P . .
H11B H 0.133711 0.250003 -0.127684 0.307 Uiso 1 2 calc R U P . .


_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 C1 1.237(3) . ?
O2 N1 1.269(5) . ?
O2 O3 1.618(6) 8_565 ?
O2 O2 1.666(11) 8_565 ?
O3 O3 1.119(14) 8_565 ?
O3 N1 1.152(5) . ?
O4 N2 1.219(4) . ?
O5 N2 1.207(4) . ?
O6 O6 1.082(9) 8_565 ?
O6 N3 1.239(4) . ?
O7 O7 0.896(9) 8_565 ?
O7 N3 1.215(4) . ?
N1 C2 1.457(4) . ?
N2 C4 1.444(4) . ?
N3 C6 1.454(4) . ?
C1 C2 1.440(4) . ?
C1 C6 1.442(4) . ?
C2 C3 1.359(4) . ?
C3 C4 1.377(4) . ?
C4 C5 1.367(4) . ?
C5 C6 1.366(4) . ?
N4 N4 1.207(10) 8_565 ?
N4 C7 1.439(5) . ?
N4 C8 1.583(5) . ?
C8 C9 1.450(4) . ?
C8 C9 1.450(4) 8_565 ?
C9 C10 1.490(6) . ?
C10 C11 1.452(7) . ?

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
N1 O2 O3 45.1(3) . 8_565 ?
N1 O2 O2 49.0(3) . 8_565 ?
O3 O2 O2 80.3(3) 8_565 8_565 ?
O3 O3 N1 60.9(4) 8_565 . ?
O3 O3 O2 99.7(3) 8_565 8_565 ?
N1 O3 O2 51.2(3) . 8_565 ?
O6 O6 N3 64.1(2) 8_565 . ?
O7 O7 N3 68.4(2) 8_565 . ?
O3 N1 O3 58.1(7) 8_565 . ?
O3 N1 O2 83.7(4) 8_565 . ?
O3 N1 O2 121.9(4) . . ?
O3 N1 O2 121.9(4) 8_565 8_565 ?
O3 N1 O2 83.7(4) . 8_565 ?
O2 N1 O2 82.0(5) . 8_565 ?
O3 N1 C2 119.4(4) 8_565 . ?
O3 N1 C2 119.4(4) . . ?
O2 N1 C2 117.2(3) . . ?
O2 N1 C2 117.2(3) 8_565 . ?
O5 N2 O4 122.7(3) . . ?
O5 N2 C4 118.8(3) . . ?
O4 N2 C4 118.5(3) . . ?
O7 N3 O7 43.3(4) . 8_565 ?
O7 N3 O6 103.9(3) . . ?
O7 N3 O6 124.2(4) 8_565 . ?
O7 N3 O6 124.2(4) . 8_565 ?
O7 N3 O6 103.9(3) 8_565 8_565 ?
O6 N3 O6 51.8(4) . 8_565 ?
O7 N3 C6 118.1(3) . . ?
O7 N3 C6 118.1(3) 8_565 . ?
O6 N3 C6 117.5(3) . . ?
O6 N3 C6 117.5(3) 8_565 . ?
O1 C1 C2 123.2(3) . . ?
O1 C1 C6 125.5(3) . . ?
C2 C1 C6 111.3(3) . . ?
C3 C2 C1 124.9(3) . . ?
C3 C2 N1 117.9(3) . . ?
C1 C2 N1 117.2(3) . . ?
C2 C3 C4 119.1(3) . . ?
C5 C4 C3 120.7(3) . . ?
C5 C4 N2 118.8(3) . . ?
C3 C4 N2 120.5(3) . . ?
C6 C5 C4 119.9(3) . . ?
C5 C6 C1 124.0(3) . . ?
C5 C6 N3 116.5(3) . . ?
C1 C6 N3 119.5(3) . . ?
N4 N4 C7 65.2(2) 8_565 . ?
N4 N4 C8 67.59(18) 8_565 . ?
C7 N4 C8 111.4(3) . . ?
N4 C7 N4 49.6(4) 8_565 . ?
C9 C8 C9 111.7(4) . 8_565 ?
C9 C8 N4 128.7(3) . 8_565 ?
C9 C8 N4 89.7(3) 8_565 8_565 ?
C9 C8 N4 89.7(3) . . ?
C9 C8 N4 128.7(3) 8_565 . ?
N4 C8 N4 44.8(4) 8_565 . ?
C8 C9 C10 108.0(4) . . ?
C11 C10 C9 110.6(5) . . ?
C10 C11 C10 110.1(6) . 8_565 ?

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
N4 H4A O1 0.923(16) 2.02(2) 2.774(4) 137.5(12) .
N4 H4B O2 0.930(19) 2.69(4) 3.196(6) 115(3) 7_656
N4 H4B O5 0.930(19) 2.46(3) 3.278(5) 147(4) 5_655
C7 H7A O6 0.96 2.41 3.016(5) 120.8 .
C7 H7A O6 0.96 2.30 3.016(5) 130.7 8_565
C7 H7B O2 0.96 2.40 3.130(5) 132.7 7_656
C7 H7C O2 0.96 2.44 3.130(5) 128.4 2_565
C8 H8 O7 0.98 2.58 3.534(5) 164.5 6_556
C8 H8 O7 0.98 2.58 3.534(5) 164.5 3_455
C9 H9A O3 0.97 2.54 3.284(6) 133.3 2

_refine_diff_density_max         0.240
_refine_diff_density_min         -0.320
_refine_diff_density_rms         0.037



####################################################################### 
# 
# 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_x_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1816475'
_audit_update_record             
;
2018-01-12 deposited with the CCDC.
2018-03-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 H2 N3 O7, C7 H16 N'
_chemical_formula_sum            'C13 H18 N4 O7'
_chemical_formula_weight         342.31

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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/n'
_space_group_name_Hall           '-P 2yn'

_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+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   6.7455(2)
_cell_length_b                   18.3207(6)
_cell_length_c                   12.8506(5)
_cell_angle_alpha                90
_cell_angle_beta                 93.473(4)
_cell_angle_gamma                90
_cell_volume                     1585.19(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    260(2)
_cell_measurement_reflns_used    4090
_cell_measurement_theta_min      4.1810
_cell_measurement_theta_max      72.4340
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.434
_exptl_crystal_F_000             720
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    1.009
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      260(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            3078
_diffrn_reflns_av_unetI/netI     0.0169
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         4.207
_diffrn_reflns_theta_max         73.074
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             3078
_reflns_number_gt                2636
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 _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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
 Refined as a 2-component twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0100P)²+2.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3078
_refine_ls_number_parameters     262
_refine_ls_number_restraints     74
_refine_ls_R_factor_all          0.0801
_refine_ls_R_factor_gt           0.0723
_refine_ls_wR_factor_ref         0.1390
_refine_ls_wR_factor_gt          0.1359
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_restrained_S_all      1.013
_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
O1 O 0.2604(4) 0.64493(11) 0.47228(17) 0.0611(7) Uani 1 1 d . . . . .
O4 O 0.2474(5) 0.33667(14) 0.6769(2) 0.0889(10) Uani 1 1 d . . . . .
O5 O 0.2244(5) 0.30739(13) 0.5152(2) 0.0813(9) Uani 1 1 d . . . . .
O2 O 0.3924(8) 0.6604(2) 0.6777(3) 0.0785(16) Uani 0.768(9) 1 d . U P A 1
O3 O 0.1784(14) 0.5992(4) 0.7593(6) 0.132(3) Uani 0.768(9) 1 d . U P A 1
O6 O 0.3067(11) 0.4883(3) 0.2534(3) 0.0785(15) Uani 0.768(9) 1 d . U P A 1
O7 O 0.1701(12) 0.5905(2) 0.2800(3) 0.090(2) Uani 0.768(9) 1 d . U P A 1
O2B O 0.192(6) 0.6649(9) 0.6738(13) 0.169(12) Uani 0.232(9) 1 d . U P A 2
O3B O 0.316(4) 0.5900(14) 0.7722(15) 0.118(9) Uani 0.232(9) 1 d . U P A 2
O6B O 0.180(3) 0.4812(9) 0.2576(11) 0.075(4) Uani 0.232(9) 1 d . U P A 2
O7B O 0.325(3) 0.5922(7) 0.2854(9) 0.061(4) Uani 0.232(9) 1 d . U P A 2
N1 N 0.2782(6) 0.60881(17) 0.6860(2) 0.0651(8) Uani 1 1 d . . . . .
N2 N 0.2404(4) 0.35275(15) 0.5849(2) 0.0594(7) Uani 1 1 d . . . . .
N3 N 0.2451(5) 0.53350(15) 0.3122(2) 0.0557(7) Uani 1 1 d . . . . .
C1 C 0.2588(4) 0.57958(15) 0.4964(2) 0.0392(6) Uani 1 1 d . . . . .
C2 C 0.2637(4) 0.55402(15) 0.6030(2) 0.0410(6) Uani 1 1 d . . . . .
C3 C 0.2568(4) 0.48264(16) 0.6331(2) 0.0450(7) Uani 1 1 d . . . . .
H3 H 0.257597 0.470211 0.703324 0.054 Uiso 1 1 calc R U . . .
C4 C 0.2486(4) 0.42910(15) 0.5567(2) 0.0422(6) Uani 1 1 d . . . . .
C5 C 0.2468(4) 0.44741(15) 0.4524(2) 0.0429(7) Uani 1 1 d . . . . .
H5 H 0.243382 0.410993 0.401933 0.051 Uiso 1 1 calc R U . . .
C6 C 0.2500(4) 0.51890(15) 0.4237(2) 0.0399(6) Uani 1 1 d . . . . .
N4 N 0.1748(6) 0.75427(16) 0.3289(2) 0.0673(9) Uani 1 1 d D . . . .
H4A H 0.212(6) 0.7156(13) 0.369(2) 0.081 Uiso 1 1 d D U . . .
H4B H 0.047(2) 0.756(2) 0.304(3) 0.081 Uiso 1 1 d D U . . .
C7 C 0.2810(8) 0.7472(2) 0.2322(3) 0.0913(16) Uani 1 1 d . . . . .
H7A H 0.263137 0.790980 0.191593 0.137 Uiso 1 1 calc R U . . .
H7B H 0.228844 0.706358 0.192615 0.137 Uiso 1 1 calc R U . . .
H7C H 0.419915 0.739787 0.249566 0.137 Uiso 1 1 calc R U . . .
C8 C 0.2233(6) 0.82297(16) 0.3907(2) 0.0559(9) Uani 1 1 d . . . . .
H8 H 0.213142 0.864527 0.342650 0.067 Uiso 1 1 calc R U . . .
C9 C 0.0710(6) 0.8325(2) 0.4695(3) 0.0769(11) Uani 1 1 d . . . . .
H9A H 0.075744 0.791379 0.517064 0.092 Uiso 1 1 calc R U . . .
H9B H -0.060572 0.834341 0.434595 0.092 Uiso 1 1 calc R U . . .
C10 C 0.1118(9) 0.9034(2) 0.5304(4) 0.1040(18) Uani 1 1 d . . . . .
H10A H 0.088630 0.944732 0.484132 0.125 Uiso 1 1 calc R U . . .
H10B H 0.020604 0.907066 0.585703 0.125 Uiso 1 1 calc R U . . .
C11 C 0.3209(9) 0.9059(3) 0.5765(3) 0.0963(16) Uani 1 1 d . . . . .
H11A H 0.345601 0.953403 0.607948 0.116 Uiso 1 1 calc R U . . .
H11B H 0.336769 0.869527 0.631310 0.116 Uiso 1 1 calc R U . . .
C12 C 0.4700(8) 0.8923(3) 0.4984(4) 0.0913(15) Uani 1 1 d . . . . .
H12A H 0.601397 0.890013 0.533301 0.110 Uiso 1 1 calc R U . . .
H12B H 0.468146 0.932410 0.449142 0.110 Uiso 1 1 calc R U . . .
C13 C 0.4278(6) 0.8215(2) 0.4401(3) 0.0680(10) Uani 1 1 d . . . . .
H13A H 0.522632 0.815193 0.386969 0.082 Uiso 1 1 calc R U . . .
H13B H 0.441702 0.780660 0.487994 0.082 Uiso 1 1 calc R 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
O1 C1 1.237(3) . ?
O4 N2 1.217(4) . ?
O5 N2 1.222(4) . ?
O2 N1 1.227(5) . ?
O3 N1 1.204(6) . ?
O6 N3 1.211(5) . ?
O7 N3 1.222(5) . ?
O2B N1 1.19(2) . ?
O3B N1 1.17(2) . ?
O6B N3 1.253(15) . ?
O7B N3 1.261(12) . ?
N1 C2 1.464(4) . ?
N2 C4 1.447(4) . ?
N3 C6 1.456(4) . ?
C1 C2 1.446(4) . ?
C1 C6 1.450(4) . ?
C2 C3 1.366(4) . ?
C3 C4 1.387(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.381(4) . ?
C5 C6 1.361(4) . ?
C5 H5 0.9300 . ?
N4 C7 1.477(5) . ?
N4 C8 1.513(4) . ?
N4 H4A 0.903(10) . ?
N4 H4B 0.902(10) . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 C13 1.483(5) . ?
C8 C9 1.496(5) . ?
C8 H8 0.9800 . ?
C9 C10 1.532(6) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C11 1.498(7) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C12 1.485(6) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.516(5) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 H13A 0.9700 . ?
C13 H13B 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
O3B N1 O2B 117.0(14) . . ?
O3 N1 O2 124.4(5) . . ?
O3B N1 C2 119.2(12) . . ?
O2B N1 C2 119.2(11) . . ?
O3 N1 C2 117.0(5) . . ?
O2 N1 C2 118.6(3) . . ?
O4 N2 O5 123.0(3) . . ?
O4 N2 C4 118.5(3) . . ?
O5 N2 C4 118.5(3) . . ?
O6 N3 O7 121.5(4) . . ?
O6B N3 O7B 129.9(10) . . ?
O6 N3 C6 120.0(3) . . ?
O7 N3 C6 118.4(3) . . ?
O6B N3 C6 113.4(8) . . ?
O7B N3 C6 116.2(6) . . ?
O1 C1 C2 123.4(3) . . ?
O1 C1 C6 125.6(3) . . ?
C2 C1 C6 111.1(2) . . ?
C3 C2 C1 125.4(3) . . ?
C3 C2 N1 116.9(3) . . ?
C1 C2 N1 117.7(3) . . ?
C2 C3 C4 118.5(3) . . ?
C2 C3 H3 120.8 . . ?
C4 C3 H3 120.8 . . ?
C5 C4 C3 120.9(3) . . ?
C5 C4 N2 118.6(3) . . ?
C3 C4 N2 120.5(3) . . ?
C6 C5 C4 119.8(3) . . ?
C6 C5 H5 120.1 . . ?
C4 C5 H5 120.1 . . ?
C5 C6 C1 124.3(3) . . ?
C5 C6 N3 116.3(3) . . ?
C1 C6 N3 119.3(2) . . ?
C7 N4 C8 114.4(3) . . ?
C7 N4 H4A 106(3) . . ?
C8 N4 H4A 108(2) . . ?
C7 N4 H4B 102(3) . . ?
C8 N4 H4B 110(3) . . ?
H4A N4 H4B 117(4) . . ?
N4 C7 H7A 109.5 . . ?
N4 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
N4 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C13 C8 C9 111.8(3) . . ?
C13 C8 N4 112.0(3) . . ?
C9 C8 N4 108.5(3) . . ?
C13 C8 H8 108.1 . . ?
C9 C8 H8 108.1 . . ?
N4 C8 H8 108.1 . . ?
C8 C9 C10 109.6(4) . . ?
C8 C9 H9A 109.7 . . ?
C10 C9 H9A 109.7 . . ?
C8 C9 H9B 109.7 . . ?
C10 C9 H9B 109.7 . . ?
H9A C9 H9B 108.2 . . ?
C11 C10 C9 111.4(4) . . ?
C11 C10 H10A 109.4 . . ?
C9 C10 H10A 109.4 . . ?
C11 C10 H10B 109.4 . . ?
C9 C10 H10B 109.4 . . ?
H10A C10 H10B 108.0 . . ?
C12 C11 C10 112.8(4) . . ?
C12 C11 H11A 109.0 . . ?
C10 C11 H11A 109.0 . . ?
C12 C11 H11B 109.0 . . ?
C10 C11 H11B 109.0 . . ?
H11A C11 H11B 107.8 . . ?
C11 C12 C13 111.3(4) . . ?
C11 C12 H12A 109.4 . . ?
C13 C12 H12A 109.4 . . ?
C11 C12 H12B 109.4 . . ?
C13 C12 H12B 109.4 . . ?
H12A C12 H12B 108.0 . . ?
C8 C13 C12 109.7(4) . . ?
C8 C13 H13A 109.7 . . ?
C12 C13 H13A 109.7 . . ?
C8 C13 H13B 109.7 . . ?
C12 C13 H13B 109.7 . . ?
H13A C13 H13B 108.2 . . ?

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
N4 H4A O1 0.903(10) 1.869(13) 2.759(3) 168(4) .
N4 H4A O7 0.903(10) 2.57(3) 3.065(5) 115(3) .
N4 H4A O7B 0.903(10) 2.63(3) 3.197(14) 121(3) .
N4 H4B O4 0.902(10) 2.63(3) 3.297(5) 131(3) 3_566
N4 H4B O2 0.902(10) 2.42(3) 3.066(5) 128(3) 4_575
C7 H7B O7 0.96 2.44 3.039(6) 119.9 .
C8 H8 O6 0.98 2.58 3.550(5) 169.5 2
C8 H8 O6B 0.98 2.62 3.552(15) 158.9 2
C9 H9B O3B 0.97 2.60 3.30(2) 129.0 4_575
C13 H13A O3 0.97 2.54 3.293(7) 134.1 4_675

_refine_diff_density_max         0.545
_refine_diff_density_min         -0.292
_refine_diff_density_rms         0.051



