# 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 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_11
_database_code_depnum_ccdc_archive 'CCDC 1529109'
_audit_update_record             
;
2017-01-22 deposited with the CCDC.
2018-02-21 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         'C9 H8 N2 O'
_chemical_formula_sum            'C9 H8 N2 O'
_chemical_formula_weight         160.17

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      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -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, -y, z+1/2'
'x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, z+1/2'

_cell_length_a                   8.6883(10)
_cell_length_b                   11.8246(16)
_cell_length_c                   15.412(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1583.3(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2749
_cell_measurement_theta_min      2.64
_cell_measurement_theta_max      21.84

_exptl_crystal_description       Block
_exptl_crystal_colour            Colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.344
_exptl_crystal_F_000             672
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.12
_exptl_absorpt_coefficient_mu    0.091
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.974
_exptl_absorpt_correction_T_max  0.989
_exptl_absorpt_process_details   multi-scan
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            21623
_diffrn_reflns_av_unetI/netI     0.0293
_diffrn_reflns_av_R_equivalents  0.0536
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.171
_diffrn_reflns_theta_max         25.248
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2874
_reflns_number_gt                2461
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.920
_reflns_Friedel_fraction_max     0.998
_reflns_Friedel_fraction_full    0.998

_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-2014/7 (Sheldrick, 2014)'
_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)+(0.0500P)²+0.0200P] 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_abs_structure_details 
;
 Flack x determined using 1012 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.7(8)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2874
_refine_ls_number_parameters     227
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0455
_refine_ls_R_factor_gt           0.0360
_refine_ls_wR_factor_ref         0.0899
_refine_ls_wR_factor_gt          0.0845
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_restrained_S_all      1.056
_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
C14 C 0.0823(3) 0.3848(2) 0.28190(19) 0.0393(6) Uani 1 1 d . . . . .
C11 C 0.0151(3) 0.3357(2) 0.20579(18) 0.0390(6) Uani 1 1 d . . . . .
C10 C 0.0524(3) 0.3679(3) 0.1177(2) 0.0478(7) Uani 1 1 d . . . . .
H10 H 0.1383 0.4144 0.1123 0.057 Uiso 1 1 calc R U . . .
C13 C 0.0254(3) 0.3249(2) 0.3534(2) 0.0440(7) Uani 1 1 d . . . . .
C5 C 0.4863(3) 0.3838(2) 0.69612(18) 0.0414(7) Uani 1 1 d . . . . .
C2 C 0.3757(3) 0.3936(2) 0.76639(19) 0.0418(7) Uani 1 1 d . . . . .
C15 C 0.1834(3) 0.4743(3) 0.2967(2) 0.0526(8) Uani 1 1 d . . . . .
H15 H 0.2200 0.5176 0.2507 0.063 Uiso 1 1 calc R U . . .
C4 C 0.4587(3) 0.4735(2) 0.63862(18) 0.0442(7) Uani 1 1 d . . . . .
C12 C -0.0781(3) 0.2498(3) 0.2340(2) 0.0473(7) Uani 1 1 d . . . . .
H12 H -0.1362 0.2029 0.1983 0.057 Uiso 1 1 calc R U . . .
C18 C 0.0671(4) 0.3491(3) 0.4377(2) 0.0558(8) Uani 1 1 d . . . . .
H18 H 0.0273 0.3086 0.4843 0.067 Uiso 1 1 calc R U . . .
C1 C 0.3684(4) 0.3181(3) 0.8389(2) 0.0503(8) Uani 1 1 d . . . . .
H1 H 0.4470 0.2648 0.8408 0.060 Uiso 1 1 calc R U . . .
C16 C 0.2278(4) 0.4973(3) 0.3802(2) 0.0630(10) Uani 1 1 d . . . . .
H16 H 0.2979 0.5552 0.3905 0.076 Uiso 1 1 calc R U . . .
C9 C 0.5449(4) 0.4895(3) 0.5643(2) 0.0543(8) Uani 1 1 d . . . . .
H9 H 0.5247 0.5488 0.5263 0.065 Uiso 1 1 calc R U . . .
C6 C 0.6041(4) 0.3080(3) 0.6778(2) 0.0515(8) Uani 1 1 d . . . . .
H6 H 0.6232 0.2470 0.7143 0.062 Uiso 1 1 calc R U . . .
C3 C 0.2876(4) 0.4870(3) 0.7472(2) 0.0488(7) Uani 1 1 d . . . . .
H3 H 0.2068 0.5138 0.7810 0.059 Uiso 1 1 calc R U . . .
C8 C 0.6621(4) 0.4135(3) 0.5489(3) 0.0623(9) Uani 1 1 d . . . . .
H8 H 0.7227 0.4221 0.4996 0.075 Uiso 1 1 calc R U . . .
C7 C 0.6918(4) 0.3247(3) 0.6050(2) 0.0608(9) Uani 1 1 d . . . . .
H7 H 0.7726 0.2755 0.5931 0.073 Uiso 1 1 calc R U . . .
C17 C 0.1707(4) 0.4360(3) 0.4496(2) 0.0633(10) Uani 1 1 d . . . . .
H17 H 0.2029 0.4539 0.5055 0.076 Uiso 1 1 calc R U . . .
N1 N 0.2726(3) 0.3116(2) 0.90140(17) 0.0508(6) Uani 1 1 d . . . . .
N3 N -0.0134(3) 0.3429(2) 0.04620(16) 0.0491(6) Uani 1 1 d . . . . .
N4 N -0.0730(3) 0.2436(3) 0.32116(17) 0.0517(7) Uani 1 1 d . . . . .
N2 N 0.3364(3) 0.5344(2) 0.67132(19) 0.0509(7) Uani 1 1 d . . . . .
O1 O 0.1577(3) 0.39360(19) 0.89531(15) 0.0557(6) Uani 1 1 d . . . . .
H1A H 0.1007 0.3891 0.9376 0.084 Uiso 1 1 calc R U . . .
O2 O -0.1481(3) 0.2810(2) 0.05951(14) 0.0564(6) Uani 1 1 d . . . . .
H2A H -0.1799 0.2573 0.0128 0.085 Uiso 1 1 calc R U . . .
H4 H -0.122(4) 0.190(3) 0.351(3) 0.064(10) Uiso 1 1 d . . . . .
H2 H 0.301(4) 0.597(3) 0.648(2) 0.052(10) Uiso 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
C14 C15 1.393(4) . ?
C14 C13 1.401(4) . ?
C14 C11 1.434(4) . ?
C11 C12 1.369(4) . ?
C11 C10 1.447(4) . ?
C10 N3 1.276(4) . ?
C13 C18 1.378(5) . ?
C13 N4 1.379(4) . ?
C5 C6 1.390(4) . ?
C5 C4 1.403(4) . ?
C5 C2 1.452(4) . ?
C2 C3 1.375(4) . ?
C2 C1 1.432(4) . ?
C15 C16 1.372(5) . ?
C4 N2 1.379(4) . ?
C4 C9 1.382(4) . ?
C12 N4 1.347(4) . ?
C18 C17 1.379(5) . ?
C1 N1 1.275(4) . ?
C16 C17 1.383(5) . ?
C9 C8 1.379(5) . ?
C6 C7 1.370(5) . ?
C3 N2 1.364(4) . ?
C8 C7 1.385(6) . ?
N1 O1 1.395(3) . ?
N3 O2 1.396(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
C15 C14 C13 118.6(3) . . ?
C15 C14 C11 134.3(3) . . ?
C13 C14 C11 107.1(2) . . ?
C12 C11 C14 106.4(3) . . ?
C12 C11 C10 128.7(3) . . ?
C14 C11 C10 124.7(3) . . ?
N3 C10 C11 130.4(3) . . ?
C18 C13 N4 130.3(3) . . ?
C18 C13 C14 122.9(3) . . ?
N4 C13 C14 106.7(3) . . ?
C6 C5 C4 119.0(3) . . ?
C6 C5 C2 133.7(3) . . ?
C4 C5 C2 107.3(3) . . ?
C3 C2 C1 130.1(3) . . ?
C3 C2 C5 105.8(3) . . ?
C1 C2 C5 124.1(3) . . ?
C16 C15 C14 118.8(3) . . ?
N2 C4 C9 130.4(3) . . ?
N2 C4 C5 107.2(3) . . ?
C9 C4 C5 122.4(3) . . ?
N4 C12 C11 109.7(3) . . ?
C13 C18 C17 116.8(3) . . ?
N1 C1 C2 131.0(3) . . ?
C15 C16 C17 121.4(3) . . ?
C8 C9 C4 116.9(3) . . ?
C7 C6 C5 118.9(3) . . ?
N2 C3 C2 110.0(3) . . ?
C9 C8 C7 121.7(3) . . ?
C6 C7 C8 121.1(3) . . ?
C18 C17 C16 121.5(3) . . ?
C1 N1 O1 112.0(3) . . ?
C10 N3 O2 111.8(2) . . ?
C12 N4 C13 110.0(3) . . ?
C3 N2 C4 109.7(3) . . ?

_refine_diff_density_max         0.105
_refine_diff_density_min         -0.132
_refine_diff_density_rms         0.029

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_exp_3173
_database_code_depnum_ccdc_archive 'CCDC 1529110'
_audit_update_record             
;
2017-01-22 deposited with the CCDC.
2018-02-21 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         'C6 H2 N3 O7, C9 H9 N2 O, O'
_chemical_formula_sum            'C15 H11 N5 O9'
_chemical_formula_weight         405.29

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

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -z'

_cell_length_a                   6.7711(6)
_cell_length_b                   8.4733(11)
_cell_length_c                   15.8026(17)
_cell_angle_alpha                78.747(10)
_cell_angle_beta                 87.742(8)
_cell_angle_gamma                75.439(10)
_cell_volume                     860.61(17)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1249
_cell_measurement_theta_min      3.55
_cell_measurement_theta_max      26.06

_exptl_crystal_description       Block
_exptl_crystal_colour            Yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.564
_exptl_crystal_F_000             416
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.11
_exptl_absorpt_coefficient_mu    0.132
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.963
_exptl_absorpt_correction_T_max  0.986
_exptl_absorpt_process_details   multi-scan
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5517
_diffrn_reflns_av_unetI/netI     0.0570
_diffrn_reflns_av_R_equivalents  0.0234
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.067
_diffrn_reflns_theta_max         25.249
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3114
_reflns_number_gt                1950
_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-2014/7 (Sheldrick, 2014)'
_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)+(0.0200P)²+2.2000P] 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         3114
_refine_ls_number_parameters     267
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1153
_refine_ls_R_factor_gt           0.0778
_refine_ls_wR_factor_ref         0.1744
_refine_ls_wR_factor_gt          0.1504
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_restrained_S_all      1.041
_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
O8 O 0.7590(5) 0.2778(4) 0.13048(18) 0.0550(9) Uani 1 1 d . . . . .
O5 O 0.8124(7) 0.2825(5) 0.5242(2) 0.0783(12) Uani 1 1 d . . . . .
O3 O 0.7323(6) 0.6037(4) 0.0842(2) 0.0740(12) Uani 1 1 d . . . . .
O2 O 0.5948(7) 0.7483(4) 0.1766(2) 0.0780(12) Uani 1 1 d . . . . .
O7 O 0.9153(7) -0.0358(4) 0.2022(2) 0.0848(13) Uani 1 1 d . . . . .
O1 O 0.1576(7) 0.7560(5) 0.0690(2) 0.0832(13) Uani 1 1 d D . . . .
H1 H 0.1845 0.8303 0.0324 0.125 Uiso 1 1 calc DR U . . .
O6 O 0.8726(6) -0.1074(4) 0.3372(2) 0.0775(12) Uani 1 1 d . . . . .
N5 N 0.6819(6) 0.6147(4) 0.1578(2) 0.0444(9) Uani 1 1 d . . . . .
O4 O 0.7288(11) 0.5417(6) 0.4718(3) 0.142(3) Uani 1 1 d . . . . .
N2 N 0.2132(5) 0.5034(4) 0.3228(2) 0.0414(9) Uani 1 1 d . . . . .
H2 H 0.1939 0.5554 0.3652 0.050 Uiso 1 1 calc R U . . .
N4 N 0.8697(6) -0.0012(4) 0.2730(3) 0.0480(9) Uani 1 1 d . . . . .
N1 N 0.2161(6) 0.6099(5) 0.0408(3) 0.0553(11) Uani 1 1 d . . . . .
N3 N 0.7700(7) 0.3968(6) 0.4633(3) 0.0652(12) Uani 1 1 d . . . . .
C15 C 0.7693(6) 0.3050(5) 0.2050(2) 0.0358(9) Uani 1 1 d . . . . .
C14 C 0.8145(6) 0.1735(5) 0.2818(3) 0.0350(9) Uani 1 1 d . . . . .
C10 C 0.7268(6) 0.4682(5) 0.2260(2) 0.0345(9) Uani 1 1 d . . . . .
C5 C 0.2668(6) 0.3315(5) 0.3311(3) 0.0363(9) Uani 1 1 d . . . . .
C12 C 0.7672(6) 0.3641(5) 0.3769(2) 0.0392(10) Uani 1 1 d . . . . .
C6 C 0.2821(6) 0.2966(5) 0.2473(3) 0.0371(9) Uani 1 1 d . . . . .
C7 C 0.2384(6) 0.4551(5) 0.1880(2) 0.0369(9) Uani 1 1 d . . . . .
C13 C 0.8122(6) 0.2022(5) 0.3637(3) 0.0392(10) Uani 1 1 d . . . . .
H13 H 0.8406 0.1138 0.4104 0.047 Uiso 1 1 calc R U . . .
C9 C 0.1956(6) 0.5768(5) 0.2385(3) 0.0420(10) Uani 1 1 d . . . . .
H9 H 0.1604 0.6908 0.2175 0.050 Uiso 1 1 calc R U . . .
C11 C 0.7251(6) 0.4978(5) 0.3083(3) 0.0393(10) Uani 1 1 d . . . . .
H11 H 0.6963 0.6061 0.3180 0.047 Uiso 1 1 calc R U . . .
C4 C 0.2992(7) 0.2068(5) 0.4041(3) 0.0454(11) Uani 1 1 d . . . . .
H4 H 0.2877 0.2314 0.4592 0.054 Uiso 1 1 calc R U . . .
C2 C 0.3645(7) 0.0080(6) 0.3097(3) 0.0539(12) Uani 1 1 d . . . . .
H2A H 0.3974 -0.1025 0.3036 0.065 Uiso 1 1 calc R U . . .
C8 C 0.2478(6) 0.4731(6) 0.0974(3) 0.0450(11) Uani 1 1 d . . . . .
H8 H 0.2807 0.3753 0.0759 0.054 Uiso 1 1 calc R U . . .
C1 C 0.3324(6) 0.1308(5) 0.2373(3) 0.0458(11) Uani 1 1 d . . . . .
H1B H 0.3438 0.1044 0.1826 0.055 Uiso 1 1 calc R U . . .
C3 C 0.3490(7) 0.0453(6) 0.3918(3) 0.0508(12) Uani 1 1 d . . . . .
H3 H 0.3727 -0.0409 0.4396 0.061 Uiso 1 1 calc R U . . .
O9 O 0.3409(10) 0.9556(6) 0.9549(3) 0.131(2) Uani 1 1 d . . . . .
H1A H 0.222(9) 0.620(8) -0.028(4) 0.12(2) Uiso 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
O8 C15 1.251(5) . ?
O5 N3 1.211(5) . ?
O3 N5 1.214(5) . ?
O2 N5 1.224(5) . ?
O7 N4 1.221(5) . ?
O1 N1 1.357(5) . ?
O6 N4 1.214(5) . ?
N5 C10 1.452(5) . ?
O4 N3 1.222(6) . ?
N2 C9 1.352(5) . ?
N2 C5 1.391(5) . ?
N4 C14 1.466(5) . ?
N1 C8 1.294(6) . ?
N3 C12 1.447(5) . ?
C15 C10 1.441(5) . ?
C15 C14 1.462(5) . ?
C14 C13 1.362(5) . ?
C10 C11 1.372(5) . ?
C5 C4 1.387(6) . ?
C5 C6 1.405(5) . ?
C12 C13 1.384(6) . ?
C12 C11 1.386(5) . ?
C6 C1 1.399(6) . ?
C6 C7 1.449(5) . ?
C7 C9 1.392(6) . ?
C7 C8 1.410(5) . ?
C4 C3 1.375(6) . ?
C2 C1 1.371(6) . ?
C2 C3 1.389(6) . ?

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
O3 N5 O2 121.3(4) . . ?
O3 N5 C10 120.1(4) . . ?
O2 N5 C10 118.6(4) . . ?
C9 N2 C5 110.1(3) . . ?
O6 N4 O7 122.0(4) . . ?
O6 N4 C14 118.7(4) . . ?
O7 N4 C14 119.3(4) . . ?
C8 N1 O1 118.3(4) . . ?
O5 N3 O4 122.1(4) . . ?
O5 N3 C12 120.1(4) . . ?
O4 N3 C12 117.8(4) . . ?
O8 C15 C10 124.3(4) . . ?
O8 C15 C14 123.4(4) . . ?
C10 C15 C14 112.1(3) . . ?
C13 C14 C15 123.9(4) . . ?
C13 C14 N4 116.1(4) . . ?
C15 C14 N4 120.1(4) . . ?
C11 C10 C15 124.3(3) . . ?
C11 C10 N5 115.6(4) . . ?
C15 C10 N5 120.1(3) . . ?
C4 C5 N2 130.6(4) . . ?
C4 C5 C6 122.1(4) . . ?
N2 C5 C6 107.3(3) . . ?
C13 C12 C11 121.4(4) . . ?
C13 C12 N3 120.1(4) . . ?
C11 C12 N3 118.5(4) . . ?
C1 C6 C5 119.0(4) . . ?
C1 C6 C7 134.2(4) . . ?
C5 C6 C7 106.8(4) . . ?
C9 C7 C8 129.3(4) . . ?
C9 C7 C6 106.4(3) . . ?
C8 C7 C6 124.2(4) . . ?
C14 C13 C12 119.3(4) . . ?
N2 C9 C7 109.3(4) . . ?
C10 C11 C12 119.0(4) . . ?
C3 C4 C5 117.4(4) . . ?
C1 C2 C3 121.4(4) . . ?
N1 C8 C7 127.6(4) . . ?
C2 C1 C6 118.7(4) . . ?
C4 C3 C2 121.5(4) . . ?

_refine_diff_density_max         1.452
_refine_diff_density_min         -0.250
_refine_diff_density_rms         0.066

####################################################################### 
# 
# 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_py-pa
_database_code_depnum_ccdc_archive 'CCDC 1529113'
_audit_update_record             
;
2017-01-22 deposited with the CCDC.
2018-02-21 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         'C6 H2 N3 O7, C6 H7 N2 O'
_chemical_formula_sum            'C12 H9 N5 O8'
_chemical_formula_weight         351.24

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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -z'

_cell_length_a                   3.8305(4)
_cell_length_b                   13.112(2)
_cell_length_c                   14.5122(18)
_cell_angle_alpha                80.380(12)
_cell_angle_beta                 82.576(10)
_cell_angle_gamma                86.434(12)
_cell_volume                     711.98(17)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1233
_cell_measurement_theta_min      3.47
_cell_measurement_theta_max      25.79

_exptl_crystal_description       Block
_exptl_crystal_colour            Yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.638
_exptl_crystal_F_000             360
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.11
_exptl_absorpt_coefficient_mu    0.141
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.960
_exptl_absorpt_correction_T_max  0.985
_exptl_absorpt_process_details   multi-scan
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4167
_diffrn_reflns_av_unetI/netI     0.0579
_diffrn_reflns_av_R_equivalents  0.0312
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.043
_diffrn_reflns_theta_max         25.049
_diffrn_reflns_theta_full        25.049
_diffrn_measured_fraction_theta_max 0.960
_diffrn_measured_fraction_theta_full 0.960
_diffrn_reflns_Laue_measured_fraction_max 0.960
_diffrn_reflns_Laue_measured_fraction_full 0.960
_diffrn_reflns_point_group_measured_fraction_max 0.960
_diffrn_reflns_point_group_measured_fraction_full 0.960
_reflns_number_total             2443
_reflns_number_gt                1720
_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-2014/7 (Sheldrick, 2014)'
_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)+(0.0010P)²+2.5000P] 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         2443
_refine_ls_number_parameters     231
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1148
_refine_ls_R_factor_gt           0.0882
_refine_ls_wR_factor_ref         0.1678
_refine_ls_wR_factor_gt          0.1540
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_restrained_S_all      1.066
_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
O8 O 0.7459(11) 0.5815(3) 0.7569(3) 0.0607(12) Uani 1 1 d . . . . .
O4 O 0.6881(11) 1.0426(3) 0.5647(3) 0.0652(12) Uani 1 1 d . . . . .
O3 O 1.1681(13) 0.5920(3) 0.5913(3) 0.0768(15) Uani 1 1 d . . . . .
N4 N 0.5167(11) 1.0011(3) 0.6362(3) 0.0399(10) Uani 1 1 d . . . . .
O1 O 0.2120(11) 1.0226(3) 0.0886(3) 0.0605(11) Uani 1 1 d . . . . .
H1 H 0.2705 1.0592 0.0381 0.091 Uiso 1 1 calc R U . . .
O2 O 0.9586(13) 0.6999(3) 0.4826(3) 0.0766(15) Uani 1 1 d . . . . .
O5 O 0.3022(12) 1.0501(3) 0.6844(3) 0.0652(12) Uani 1 1 d . . . . .
N3 N 0.9888(12) 0.6679(3) 0.5660(3) 0.0463(11) Uani 1 1 d . . . . .
N2 N 0.7948(13) 0.5763(3) 0.2400(3) 0.0466(11) Uani 1 1 d D . . . .
O6 O 0.1938(16) 0.7599(4) 0.9302(3) 0.112(2) Uani 1 1 d . . . . .
N1 N 0.3968(11) 0.9276(3) 0.0920(3) 0.0439(11) Uani 1 1 d . . . . .
O7 O 0.386(2) 0.6159(4) 0.9145(4) 0.155(4) Uani 1 1 d . . . . .
N5 N 0.3488(13) 0.7042(4) 0.8828(3) 0.0505(12) Uani 1 1 d . . . . .
C2 C 0.4902(12) 0.7662(4) 0.1929(3) 0.0348(11) Uani 1 1 d . . . . .
C9 C 0.5664(12) 0.8914(3) 0.6674(3) 0.0334(10) Uani 1 1 d . . . . .
C12 C 0.6886(13) 0.6746(4) 0.7292(3) 0.0376(11) Uani 1 1 d . . . . .
C7 C 0.8075(12) 0.7271(3) 0.6350(3) 0.0348(11) Uani 1 1 d . . . . .
C1 C 0.3253(13) 0.8713(4) 0.1719(3) 0.0401(12) Uani 1 1 d . . . . .
H1A H 0.1672 0.8966 0.2178 0.048 Uiso 1 1 calc R U . . .
C10 C 0.4340(12) 0.8478(4) 0.7572(3) 0.0381(11) Uani 1 1 d . . . . .
H10 H 0.3069 0.8885 0.7977 0.046 Uiso 1 1 calc R U . . .
C8 C 0.7485(12) 0.8318(4) 0.6048(3) 0.0363(11) Uani 1 1 d . . . . .
H8 H 0.8294 0.8618 0.5436 0.044 Uiso 1 1 calc R U . . .
C3 C 0.6646(13) 0.7144(4) 0.1243(4) 0.0419(12) Uani 1 1 d . . . . .
H3 H 0.6784 0.7443 0.0612 0.050 Uiso 1 1 calc R U . . .
C4 C 0.8163(14) 0.6193(4) 0.1500(4) 0.0490(13) Uani 1 1 d . . . . .
H4 H 0.9362 0.5840 0.1042 0.059 Uiso 1 1 calc R U . . .
C11 C 0.4920(13) 0.7435(4) 0.7864(3) 0.0365(11) Uani 1 1 d . . . . .
C5 C 0.6285(16) 0.6241(4) 0.3081(4) 0.0499(14) Uani 1 1 d . . . . .
H5 H 0.6199 0.5924 0.3706 0.060 Uiso 1 1 calc R U . . .
C6 C 0.4708(14) 0.7196(4) 0.2862(4) 0.0462(13) Uani 1 1 d . . . . .
H6 H 0.3515 0.7531 0.3334 0.055 Uiso 1 1 calc R U . . .
H2 H 0.94(2) 0.523(5) 0.247(7) 0.18(5) Uiso 1 1 d 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
O8 C12 1.235(6) . ?
O4 N4 1.218(5) . ?
O3 N3 1.206(6) . ?
N4 O5 1.230(5) . ?
N4 C9 1.443(6) . ?
O1 N1 1.391(5) . ?
O2 N3 1.230(5) . ?
N3 C7 1.450(6) . ?
N2 C4 1.328(7) . ?
N2 C5 1.330(7) . ?
O6 N5 1.170(6) . ?
N1 C1 1.274(6) . ?
O7 N5 1.178(6) . ?
N5 C11 1.456(6) . ?
C2 C3 1.376(6) . ?
C2 C6 1.384(7) . ?
C2 C1 1.481(6) . ?
C9 C10 1.378(6) . ?
C9 C8 1.389(6) . ?
C12 C11 1.441(7) . ?
C12 C7 1.454(6) . ?
C7 C8 1.383(6) . ?
C10 C11 1.376(7) . ?
C3 C4 1.357(7) . ?
C5 C6 1.362(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
O4 N4 O5 122.0(4) . . ?
O4 N4 C9 119.9(4) . . ?
O5 N4 C9 118.0(4) . . ?
O3 N3 O2 122.8(4) . . ?
O3 N3 C7 119.8(4) . . ?
O2 N3 C7 117.4(4) . . ?
C4 N2 C5 121.9(5) . . ?
C1 N1 O1 110.7(4) . . ?
O6 N5 O7 118.8(5) . . ?
O6 N5 C11 120.3(5) . . ?
O7 N5 C11 120.9(5) . . ?
C3 C2 C6 119.3(5) . . ?
C3 C2 C1 123.0(4) . . ?
C6 C2 C1 117.7(4) . . ?
C10 C9 C8 121.5(4) . . ?
C10 C9 N4 120.2(4) . . ?
C8 C9 N4 118.3(4) . . ?
O8 C12 C11 123.8(4) . . ?
O8 C12 C7 124.0(5) . . ?
C11 C12 C7 112.2(4) . . ?
C8 C7 N3 116.6(4) . . ?
C8 C7 C12 123.9(4) . . ?
N3 C7 C12 119.5(4) . . ?
N1 C1 C2 121.0(4) . . ?
C11 C10 C9 119.2(4) . . ?
C7 C8 C9 118.8(4) . . ?
C4 C3 C2 119.1(5) . . ?
N2 C4 C3 120.5(5) . . ?
C10 C11 C12 124.4(4) . . ?
C10 C11 N5 115.7(4) . . ?
C12 C11 N5 119.9(4) . . ?
N2 C5 C6 120.0(5) . . ?
C5 C6 C2 119.2(5) . . ?

_refine_diff_density_max         0.304
_refine_diff_density_min         -0.289
_refine_diff_density_rms         0.068

####################################################################### 
# 
# 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_11_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1529114'
_audit_update_record             
;
2017-01-22 deposited with the CCDC.
2018-02-21 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         'C6 H2 N3 O7, C10 H9 N2 O, H2 O'
_chemical_formula_sum            'C16 H13 N5 O9'
_chemical_formula_weight         419.31

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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/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                   17.0234(15)
_cell_length_b                   4.9886(5)
_cell_length_c                   22.731(2)
_cell_angle_alpha                90
_cell_angle_beta                 109.651(5)
_cell_angle_gamma                90
_cell_volume                     1818.0(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2264
_cell_measurement_theta_min      2.54
_cell_measurement_theta_max      20.18

_exptl_crystal_description       Needle
_exptl_crystal_colour            Yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.532
_exptl_crystal_F_000             864
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.12
_exptl_absorpt_coefficient_mu    0.128
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.964
_exptl_absorpt_correction_T_max  0.985
_exptl_absorpt_process_details   multi-scan
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            17126
_diffrn_reflns_av_unetI/netI     0.0772
_diffrn_reflns_av_R_equivalents  0.0545
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         1.825
_diffrn_reflns_theta_max         25.245
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measured_fraction_theta_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_point_group_measured_fraction_full 0.985
_reflns_number_total             3225
_reflns_number_gt                1776
_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-2014/7 (Sheldrick, 2014)'
_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)+(0.0700P)²+0.1778P] 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         3225
_refine_ls_number_parameters     284
_refine_ls_number_restraints     5
_refine_ls_R_factor_all          0.1107
_refine_ls_R_factor_gt           0.0534
_refine_ls_wR_factor_ref         0.1572
_refine_ls_wR_factor_gt          0.1259
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_restrained_S_all      1.006
_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
C2 C -0.02299(17) 0.3648(6) 0.12533(12) 0.0458(7) Uani 1 1 d . . . . .
C10 C 0.04866(18) 0.7254(6) 0.19589(13) 0.0464(7) Uani 1 1 d . . . . .
C9 C 0.04572(17) 0.5486(6) 0.14666(13) 0.0463(7) Uani 1 1 d . . . . .
C4 C -0.0770(2) 0.5471(6) 0.20095(14) 0.0554(8) Uani 1 1 d . . . . .
H4 H -0.1181 0.5474 0.2194 0.067 Uiso 1 1 calc R U . . .
C5 C 0.11489(19) 0.9078(6) 0.21966(14) 0.0578(8) Uani 1 1 d . . . . .
H5 H 0.1172 1.0191 0.2530 0.069 Uiso 1 1 calc R U . . .
C3 C -0.08265(18) 0.3695(6) 0.15371(13) 0.0526(8) Uani 1 1 d . . . . .
H3 H -0.1273 0.2509 0.1407 0.063 Uiso 1 1 calc R U . . .
C1 C -0.0300(2) 0.1749(7) 0.07519(14) 0.0584(9) Uani 1 1 d . . . . .
H1 H 0.0081 0.1761 0.0539 0.070 Uiso 1 1 calc R U . . .
C8 C 0.11059(19) 0.5666(6) 0.12096(15) 0.0602(9) Uani 1 1 d . . . . .
H8 H 0.1104 0.4533 0.0884 0.072 Uiso 1 1 calc R U . . .
C6 C 0.1758(2) 0.9187(7) 0.19290(15) 0.0669(9) Uani 1 1 d . . . . .
H6 H 0.2193 1.0406 0.2077 0.080 Uiso 1 1 calc R U . . .
C7 C 0.1732(2) 0.7483(7) 0.14348(16) 0.0699(10) Uani 1 1 d . . . . .
H7 H 0.2149 0.7594 0.1257 0.084 Uiso 1 1 calc R U . . .
C14 C 0.61697(16) 0.7236(6) 0.16423(12) 0.0450(7) Uani 1 1 d . . . . .
C12 C 0.48722(16) 0.9507(6) 0.11833(12) 0.0454(7) Uani 1 1 d . . . . .
C11 C 0.52198(18) 1.1037(6) 0.08348(13) 0.0515(8) Uani 1 1 d . . . . .
H11 H 0.4901 1.2320 0.0561 0.062 Uiso 1 1 calc R U . . .
C13 C 0.53035(17) 0.7373(6) 0.15998(13) 0.0473(7) Uani 1 1 d . . . . .
C15 C 0.65250(17) 0.8770(6) 0.12973(12) 0.0487(8) Uani 1 1 d . . . . .
H15 H 0.7082 0.8531 0.1336 0.058 Uiso 1 1 calc R U . . .
C16 C 0.60490(18) 1.0662(6) 0.08931(13) 0.0493(8) Uani 1 1 d . . . . .
N2 N -0.01408(16) 0.7184(5) 0.22089(11) 0.0514(7) Uani 1 1 d D . . . .
N3 N 0.40116(16) 1.0072(5) 0.11193(14) 0.0601(7) Uani 1 1 d . . . . .
N1 N -0.08994(16) 0.0065(5) 0.06137(11) 0.0575(7) Uani 1 1 d . . . . .
N4 N 0.67208(16) 0.5354(5) 0.20821(13) 0.0532(7) Uani 1 1 d . . . . .
N5 N 0.64346(18) 1.2316(6) 0.05415(12) 0.0619(7) Uani 1 1 d . . . . .
O8 O 0.49506(12) 0.5793(4) 0.18572(9) 0.0617(6) Uani 1 1 d . . . . .
O9 O 0.22282(15) 0.4718(6) 0.02018(13) 0.0733(7) Uani 1 1 d D . . . .
O4 O 0.65713(13) 0.4793(4) 0.25583(11) 0.0692(7) Uani 1 1 d . . . . .
O3 O 0.37763(14) 0.9784(5) 0.15652(12) 0.0849(8) Uani 1 1 d . . . . .
O5 O 0.73211(14) 0.4482(4) 0.19606(10) 0.0696(7) Uani 1 1 d . . . . .
O1 O -0.08929(13) -0.1652(5) 0.01430(10) 0.0743(7) Uani 1 1 d . . . . .
H1A H -0.1323 -0.2542 0.0034 0.111 Uiso 1 1 calc R U . . .
O6 O 0.71780(15) 1.1959(5) 0.06214(10) 0.0813(8) Uani 1 1 d . . . . .
O7 O 0.59994(16) 1.3987(5) 0.01766(11) 0.0822(7) Uani 1 1 d . . . . .
O2 O 0.35507(14) 1.0887(5) 0.06091(12) 0.0915(8) Uani 1 1 d . . . . .
H2 H -0.014(2) 0.834(7) 0.2509(14) 0.109(14) Uiso 1 1 d D . . . .
H9A H 0.238(3) 0.568(9) -0.005(2) 0.17(2) Uiso 1 1 d D . . . .
H9B H 0.2627(18) 0.361(6) 0.0362(17) 0.109(16) Uiso 1 1 d 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
C2 C3 1.375(4) . ?
C2 C9 1.436(4) . ?
C2 C1 1.456(4) . ?
C10 N2 1.369(3) . ?
C10 C5 1.408(4) . ?
C10 C9 1.412(4) . ?
C9 C8 1.415(4) . ?
C4 N2 1.325(4) . ?
C4 C3 1.370(4) . ?
C5 C6 1.368(4) . ?
C1 N1 1.277(4) . ?
C8 C7 1.361(4) . ?
C6 C7 1.397(4) . ?
C14 C15 1.373(3) . ?
C14 C13 1.447(4) . ?
C14 N4 1.460(3) . ?
C12 C11 1.370(4) . ?
C12 C13 1.449(4) . ?
C12 N3 1.450(4) . ?
C11 C16 1.385(4) . ?
C13 O8 1.249(3) . ?
C15 C16 1.375(4) . ?
C16 N5 1.450(4) . ?
N3 O3 1.217(3) . ?
N3 O2 1.230(3) . ?
N1 O1 1.374(3) . ?
N4 O4 1.225(3) . ?
N4 O5 1.225(3) . ?
N5 O6 1.230(3) . ?
N5 O7 1.232(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
C3 C2 C9 118.5(3) . . ?
C3 C2 C1 120.0(3) . . ?
C9 C2 C1 121.5(3) . . ?
N2 C10 C5 119.5(3) . . ?
N2 C10 C9 119.2(3) . . ?
C5 C10 C9 121.2(3) . . ?
C10 C9 C8 117.6(3) . . ?
C10 C9 C2 118.3(2) . . ?
C8 C9 C2 124.1(3) . . ?
N2 C4 C3 121.4(3) . . ?
C6 C5 C10 118.9(3) . . ?
C4 C3 C2 120.7(3) . . ?
N1 C1 C2 117.9(3) . . ?
C7 C8 C9 120.5(3) . . ?
C5 C6 C7 120.6(3) . . ?
C8 C7 C6 121.1(3) . . ?
C15 C14 C13 124.8(3) . . ?
C15 C14 N4 116.4(3) . . ?
C13 C14 N4 118.8(2) . . ?
C11 C12 C13 124.4(3) . . ?
C11 C12 N3 116.9(3) . . ?
C13 C12 N3 118.7(2) . . ?
C12 C11 C16 119.6(3) . . ?
O8 C13 C14 125.4(3) . . ?
O8 C13 C12 123.5(3) . . ?
C14 C13 C12 111.1(2) . . ?
C14 C15 C16 119.4(3) . . ?
C15 C16 C11 120.6(3) . . ?
C15 C16 N5 119.0(3) . . ?
C11 C16 N5 120.4(3) . . ?
C4 N2 C10 121.9(3) . . ?
O3 N3 O2 122.7(3) . . ?
O3 N3 C12 119.9(3) . . ?
O2 N3 C12 117.5(3) . . ?
C1 N1 O1 112.7(2) . . ?
O4 N4 O5 123.7(3) . . ?
O4 N4 C14 118.4(3) . . ?
O5 N4 C14 117.8(3) . . ?
O6 N5 O7 123.6(3) . . ?
O6 N5 C16 118.0(3) . . ?
O7 N5 C16 118.3(3) . . ?

_refine_diff_density_max         0.230
_refine_diff_density_min         -0.218
_refine_diff_density_rms         0.046

####################################################################### 
# 
# 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_11_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 1529111'
_audit_update_record             
;
2017-01-22 deposited with the CCDC.
2018-02-21 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         'C6 H2 N3 O7, C9 H13 N2 O'
_chemical_formula_sum            'C15 H15 N5 O8'
_chemical_formula_weight         393.32

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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -z'

_cell_length_a                   7.2191(7)
_cell_length_b                   10.8361(8)
_cell_length_c                   11.3880(9)
_cell_angle_alpha                96.925(5)
_cell_angle_beta                 100.591(5)
_cell_angle_gamma                94.292(5)
_cell_volume                     864.98(13)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3612
_cell_measurement_theta_min      2.46
_cell_measurement_theta_max      28.14

_exptl_crystal_description       Block
_exptl_crystal_colour            Brown
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.510
_exptl_crystal_F_000             408
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.11
_exptl_absorpt_coefficient_mu    0.125
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.965
_exptl_absorpt_correction_T_max  0.986
_exptl_absorpt_process_details   multi-scan
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12241
_diffrn_reflns_av_unetI/netI     0.0202
_diffrn_reflns_av_R_equivalents  0.0242
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         1.837
_diffrn_reflns_theta_max         25.050
_diffrn_reflns_theta_full        25.050
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measured_fraction_theta_full 0.981
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_Laue_measured_fraction_full 0.981
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_point_group_measured_fraction_full 0.981
_reflns_number_total             3006
_reflns_number_gt                2382
_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-2014/7 (Sheldrick, 2014)'
_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)+(0.0500P)²+0.4000P] 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         3006
_refine_ls_number_parameters     260
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0560
_refine_ls_R_factor_gt           0.0452
_refine_ls_wR_factor_ref         0.1165
_refine_ls_wR_factor_gt          0.1094
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_restrained_S_all      1.031
_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
C2 C 0.0347(3) 0.68397(16) 0.74195(16) 0.0356(4) Uani 1 1 d . . . . .
C12 C 0.5276(3) 0.30328(17) 0.33733(17) 0.0397(4) Uani 1 1 d . . . . .
H12 H 0.5773 0.3543 0.4097 0.048 Uiso 1 1 calc R U . . .
C1 C 0.0064(3) 0.81358(17) 0.72634(18) 0.0412(4) Uani 1 1 d . . . . .
H1 H 0.0575 0.8773 0.7887 0.049 Uiso 1 1 calc R U . . .
C11 C 0.4432(3) 0.35370(16) 0.23973(17) 0.0378(4) Uani 1 1 d . . . . .
C13 C 0.5390(3) 0.17581(17) 0.32816(17) 0.0398(4) Uani 1 1 d . . . . .
C5 C 0.0840(3) 0.44026(16) 0.77854(16) 0.0372(4) Uani 1 1 d . . . . .
C7 C 0.1359(3) 0.65718(17) 0.85007(17) 0.0398(4) Uani 1 1 d . . . . .
H7 H 0.1877 0.7223 0.9109 0.048 Uiso 1 1 calc R U . . .
C10 C 0.3743(3) 0.14900(17) 0.12584(17) 0.0407(4) Uani 1 1 d . . . . .
C6 C 0.1613(3) 0.53544(17) 0.86930(17) 0.0394(4) Uani 1 1 d . . . . .
H6 H 0.2293 0.5184 0.9422 0.047 Uiso 1 1 calc R U . . .
C4 C -0.0174(3) 0.46373(18) 0.66981(17) 0.0441(5) Uani 1 1 d . . . . .
H4 H -0.0688 0.3982 0.6094 0.053 Uiso 1 1 calc R U . . .
C14 C 0.4600(3) 0.09804(18) 0.22286(17) 0.0415(5) Uani 1 1 d . . . . .
H14 H 0.4652 0.0121 0.2182 0.050 Uiso 1 1 calc R U . . .
C3 C -0.0417(3) 0.58539(18) 0.65191(17) 0.0431(5) Uani 1 1 d . . . . .
H3 H -0.1098 0.6018 0.5788 0.052 Uiso 1 1 calc R U . . .
C8 C 0.1870(3) 0.23719(18) 0.7051(2) 0.0524(5) Uani 1 1 d . . . . .
H8A H 0.1064 0.2346 0.6276 0.079 Uiso 1 1 calc R U . . .
H8B H 0.1985 0.1536 0.7235 0.079 Uiso 1 1 calc R U . . .
H8C H 0.3099 0.2769 0.7039 0.079 Uiso 1 1 calc R U . . .
C9 C -0.0826(3) 0.24596(19) 0.8110(2) 0.0531(5) Uani 1 1 d . . . . .
H9A H -0.1282 0.2912 0.8760 0.080 Uiso 1 1 calc R U . . .
H9B H -0.0660 0.1622 0.8274 0.080 Uiso 1 1 calc R U . . .
H9C H -0.1727 0.2437 0.7372 0.080 Uiso 1 1 calc R U . . .
N2 N 0.1029(2) 0.30955(14) 0.79921(15) 0.0412(4) Uani 1 1 d . . . . .
N1 N -0.0874(2) 0.83991(14) 0.62837(16) 0.0476(4) Uani 1 1 d . . . . .
N4 N 0.6375(2) 0.12352(16) 0.42842(15) 0.0484(4) Uani 1 1 d . . . . .
N3 N 0.4448(2) 0.48942(15) 0.25571(17) 0.0464(4) Uani 1 1 d . . . . .
N5 N 0.2929(3) 0.06098(17) 0.01882(17) 0.0561(5) Uani 1 1 d . . . . .
C15 C 0.3582(3) 0.28157(18) 0.12422(17) 0.0404(4) Uani 1 1 d . . . . .
O5 O 0.6481(2) 0.00984(14) 0.41789(14) 0.0620(4) Uani 1 1 d . . . . .
O2 O 0.2753(2) 0.32653(14) 0.03654(13) 0.0605(4) Uani 1 1 d . . . . .
O1 O -0.0993(3) 0.96828(13) 0.63520(15) 0.0632(5) Uani 1 1 d . . . . .
H1A H -0.1610 0.9840 0.5718 0.095 Uiso 1 1 calc R U . . .
O6 O 0.7098(3) 0.19307(16) 0.52093(14) 0.0736(5) Uani 1 1 d . . . . .
O7 O 0.4127(3) 0.54358(14) 0.16800(16) 0.0737(5) Uani 1 1 d . . . . .
O8 O 0.4833(3) 0.54543(14) 0.35787(15) 0.0727(5) Uani 1 1 d . . . . .
O4 O 0.2603(4) -0.04638(18) 0.02733(17) 0.1075(9) Uani 1 1 d . . . . .
O3 O 0.2762(4) 0.09593(18) -0.07959(17) 0.1100(9) Uani 1 1 d . . . . .
H2 H 0.180(3) 0.3099(19) 0.875(2) 0.047(6) Uiso 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
C2 C7 1.386(3) . ?
C2 C3 1.391(3) . ?
C2 C1 1.461(2) . ?
C12 C11 1.361(3) . ?
C12 C13 1.382(3) . ?
C1 N1 1.270(2) . ?
C11 C15 1.450(3) . ?
C11 N3 1.459(2) . ?
C13 C14 1.381(3) . ?
C13 N4 1.431(2) . ?
C5 C6 1.374(3) . ?
C5 C4 1.380(3) . ?
C5 N2 1.476(2) . ?
C7 C6 1.383(2) . ?
C10 C14 1.362(3) . ?
C10 C15 1.452(3) . ?
C10 N5 1.453(2) . ?
C4 C3 1.377(3) . ?
C8 N2 1.496(3) . ?
C9 N2 1.495(3) . ?
N1 O1 1.394(2) . ?
N4 O6 1.224(2) . ?
N4 O5 1.233(2) . ?
N3 O7 1.213(2) . ?
N3 O8 1.218(2) . ?
N5 O4 1.189(2) . ?
N5 O3 1.214(2) . ?
C15 O2 1.238(2) . ?

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
C7 C2 C3 118.61(17) . . ?
C7 C2 C1 119.64(17) . . ?
C3 C2 C1 121.73(17) . . ?
C11 C12 C13 119.56(18) . . ?
N1 C1 C2 120.58(18) . . ?
C12 C11 C15 124.15(17) . . ?
C12 C11 N3 115.94(17) . . ?
C15 C11 N3 119.89(16) . . ?
C14 C13 C12 121.08(17) . . ?
C14 C13 N4 119.27(17) . . ?
C12 C13 N4 119.64(17) . . ?
C6 C5 C4 121.54(17) . . ?
C6 C5 N2 119.41(16) . . ?
C4 C5 N2 119.01(16) . . ?
C6 C7 C2 121.27(17) . . ?
C14 C10 C15 124.62(17) . . ?
C14 C10 N5 115.73(17) . . ?
C15 C10 N5 119.64(17) . . ?
C5 C6 C7 118.65(17) . . ?
C3 C4 C5 119.20(18) . . ?
C10 C14 C13 119.02(17) . . ?
C4 C3 C2 120.73(18) . . ?
C5 N2 C9 110.89(15) . . ?
C5 N2 C8 112.74(15) . . ?
C9 N2 C8 111.46(16) . . ?
C1 N1 O1 110.40(17) . . ?
O6 N4 O5 122.35(17) . . ?
O6 N4 C13 119.02(17) . . ?
O5 N4 C13 118.62(16) . . ?
O7 N3 O8 121.87(17) . . ?
O7 N3 C11 119.72(17) . . ?
O8 N3 C11 118.38(17) . . ?
O4 N5 O3 120.5(2) . . ?
O4 N5 C10 119.85(19) . . ?
O3 N5 C10 119.26(19) . . ?
O2 C15 C11 124.36(17) . . ?
O2 C15 C10 124.06(18) . . ?
C11 C15 C10 111.52(16) . . ?

_refine_diff_density_max         0.475
_refine_diff_density_min         -0.293
_refine_diff_density_rms         0.065

