# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry A.
# 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_sh323
_database_code_depnum_ccdc_archive 'CCDC 1854060'
_audit_update_record             
;
2018-07-05 deposited with the CCDC.
2018-09-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C7 H4 N4 O4'
_chemical_formula_sum            'C7 H4 N4 O4'
_chemical_formula_weight         208.14

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

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

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

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

_cell_length_a                   12.608(3)
_cell_length_b                   5.6499(11)
_cell_length_c                   12.102(2)
_cell_angle_alpha                90
_cell_angle_beta                 110.626(4)
_cell_angle_gamma                90
_cell_volume                     806.8(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    1921
_cell_measurement_theta_min      3.40
_cell_measurement_theta_max      29.65

_exptl_crystal_description       prizm
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.714
_exptl_crystal_F_000             424
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.16
_exptl_absorpt_coefficient_mu    0.144
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13624
_diffrn_reflns_av_unetI/netI     0.0452
_diffrn_reflns_av_R_equivalents  0.0642
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.398
_diffrn_reflns_theta_max         30.032
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2354
_reflns_number_gt                1631
_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       'APEX (Bruker, 2009)'
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_reduction        'SAINT (Bruker, 2009)'
_computing_structure_solution    'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_publication_material  
'SHELXL-2014/6 (Sheldrick, 2014) and PLATON (Spek, 2009)'
_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)+(0.0434P)²+0.1712P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2354
_refine_ls_number_parameters     136
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0711
_refine_ls_R_factor_gt           0.0418
_refine_ls_wR_factor_ref         0.1062
_refine_ls_wR_factor_gt          0.0921
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_restrained_S_all      1.015
_refine_ls_shift/su_max          0.001
_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 0.60344(9) 0.10078(19) 0.82908(10) 0.0287(3) Uani 1 1 d . . . . .
O2 O 0.41639(10) 0.1037(2) 0.80812(9) 0.0308(3) Uani 1 1 d . . . . .
O3 O 0.89651(10) -1.0693(2) 1.23807(11) 0.0376(3) Uani 1 1 d . . . . .
O4 O 0.99950(10) -1.0237(2) 1.13110(10) 0.0324(3) Uani 1 1 d . . . . .
N1 N 0.69245(11) -0.0444(2) 0.88201(12) 0.0266(3) Uani 1 1 d . . . . .
N2 N 0.64948(10) -0.2053(2) 0.92892(10) 0.0208(3) Uani 1 1 d . . . . .
N3 N 0.54117(11) -0.1898(2) 0.91569(11) 0.0238(3) Uani 1 1 d . . . . .
N4 N 0.92125(11) -0.9660(2) 1.16208(11) 0.0248(3) Uani 1 1 d . . . . .
C1 C 0.50636(14) 0.0083(3) 0.84896(13) 0.0249(3) Uani 1 1 d . . . . .
C2 C 0.71997(12) -0.3986(2) 0.99078(12) 0.0203(3) Uani 1 1 d . . . . .
C3 C 0.81194(12) -0.4582(3) 0.96022(13) 0.0231(3) Uani 1 1 d . . . . .
H3A H 0.8287 -0.3726 0.9008 0.028 Uiso 1 1 calc R U . . .
C4 C 0.87910(12) -0.6449(3) 1.01787(13) 0.0237(3) Uani 1 1 d . . . . .
H4A H 0.9430 -0.6919 0.9989 0.028 Uiso 1 1 calc R U . . .
C5 C 0.85108(12) -0.7614(3) 1.10376(12) 0.0208(3) Uani 1 1 d . . . . .
C6 C 0.75932(13) -0.7028(3) 1.13421(13) 0.0254(3) Uani 1 1 d . . . . .
H6A H 0.7428 -0.7886 1.1937 0.030 Uiso 1 1 calc R U . . .
C7 C 0.69136(13) -0.5156(3) 1.07626(13) 0.0242(3) Uani 1 1 d . . . . .
H7A H 0.6271 -0.4695 1.0948 0.029 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 N1 1.3549(17) . ?
O1 C1 1.4272(19) . ?
O2 C1 1.1946(19) . ?
O3 N4 1.2188(17) . ?
O4 N4 1.2168(16) . ?
N1 N2 1.2882(17) . ?
N2 N3 1.3206(17) . ?
N2 C2 1.4404(18) . ?
N3 C1 1.359(2) . ?
N4 C5 1.4757(19) . ?
C2 C3 1.377(2) . ?
C2 C7 1.378(2) . ?
C3 C4 1.378(2) . ?
C3 H3A 0.9500 . ?
C4 C5 1.377(2) . ?
C4 H4A 0.9500 . ?
C5 C6 1.373(2) . ?
C6 C7 1.386(2) . ?
C6 H6A 0.9500 . ?
C7 H7A 0.9500 . ?

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 O1 C1 108.38(11) . . ?
N2 N1 O1 103.22(12) . . ?
N1 N2 N3 118.51(12) . . ?
N1 N2 C2 119.09(12) . . ?
N3 N2 C2 122.38(12) . . ?
N2 N3 C1 103.31(12) . . ?
O4 N4 O3 123.72(13) . . ?
O4 N4 C5 118.48(13) . . ?
O3 N4 C5 117.79(13) . . ?
O2 C1 N3 132.72(16) . . ?
O2 C1 O1 120.70(14) . . ?
N3 C1 O1 106.57(13) . . ?
C3 C2 C7 123.50(14) . . ?
C3 C2 N2 118.00(13) . . ?
C7 C2 N2 118.50(13) . . ?
C2 C3 C4 118.44(13) . . ?
C2 C3 H3A 120.8 . . ?
C4 C3 H3A 120.8 . . ?
C5 C4 C3 118.19(14) . . ?
C5 C4 H4A 120.9 . . ?
C3 C4 H4A 120.9 . . ?
C6 C5 C4 123.49(14) . . ?
C6 C5 N4 118.72(13) . . ?
C4 C5 N4 117.74(13) . . ?
C5 C6 C7 118.52(14) . . ?
C5 C6 H6A 120.7 . . ?
C7 C6 H6A 120.7 . . ?
C2 C7 C6 117.85(14) . . ?
C2 C7 H7A 121.1 . . ?
C6 C7 H7A 121.1 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 O1 N1 N2 -0.44(14) . . . . ?
O1 N1 N2 N3 -0.30(16) . . . . ?
O1 N1 N2 C2 177.94(11) . . . . ?
N1 N2 N3 C1 0.92(16) . . . . ?
C2 N2 N3 C1 -177.25(12) . . . . ?
N2 N3 C1 O2 178.03(17) . . . . ?
N2 N3 C1 O1 -1.08(14) . . . . ?
N1 O1 C1 O2 -178.25(13) . . . . ?
N1 O1 C1 N3 0.99(15) . . . . ?
N1 N2 C2 C3 -25.12(19) . . . . ?
N3 N2 C2 C3 153.05(13) . . . . ?
N1 N2 C2 C7 155.57(14) . . . . ?
N3 N2 C2 C7 -26.3(2) . . . . ?
C7 C2 C3 C4 0.1(2) . . . . ?
N2 C2 C3 C4 -179.20(13) . . . . ?
C2 C3 C4 C5 -0.4(2) . . . . ?
C3 C4 C5 C6 0.6(2) . . . . ?
C3 C4 C5 N4 177.98(13) . . . . ?
O4 N4 C5 C6 176.81(14) . . . . ?
O3 N4 C5 C6 -2.5(2) . . . . ?
O4 N4 C5 C4 -0.7(2) . . . . ?
O3 N4 C5 C4 -179.97(14) . . . . ?
C4 C5 C6 C7 -0.4(2) . . . . ?
N4 C5 C6 C7 -177.77(13) . . . . ?
C3 C2 C7 C6 0.1(2) . . . . ?
N2 C2 C7 C6 179.37(13) . . . . ?
C5 C6 C7 C2 0.1(2) . . . . ?

_refine_diff_density_max         0.304
_refine_diff_density_min         -0.224
_refine_diff_density_rms         0.054

_shelxl_version_number           2014/6

####################################################################### 
# 
# 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_sh330
_database_code_depnum_ccdc_archive 'CCDC 1854061'
_audit_update_record             
;
2018-07-05 deposited with the CCDC.
2018-09-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C7 H4 N4 O4'
_chemical_formula_sum            'C7 H4 N4 O4'
_chemical_formula_weight         208.14

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                   5.3726(12)
_cell_length_b                   17.510(4)
_cell_length_c                   8.6127(19)
_cell_angle_alpha                90
_cell_angle_beta                 93.895(5)
_cell_angle_gamma                90
_cell_volume                     808.4(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    4043
_cell_measurement_theta_min      2.33
_cell_measurement_theta_max      29.07

_exptl_crystal_description       prizm
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.710
_exptl_crystal_F_000             424
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.18
_exptl_absorpt_coefficient_mu    0.144
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15218
_diffrn_reflns_av_unetI/netI     0.0209
_diffrn_reflns_av_R_equivalents  0.0399
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.326
_diffrn_reflns_theta_max         27.996
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             1943
_reflns_number_gt                1562
_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       'APEX (Bruker, 2009)'
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_reduction        'SAINT (Bruker, 2009)'
_computing_structure_solution    'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_publication_material  
'SHELXL-2014/6 (Sheldrick, 2014) and PLATON (Spek, 2009)'
_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)+(0.0429P)²+0.2871P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1943
_refine_ls_number_parameters     136
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0482
_refine_ls_R_factor_gt           0.0350
_refine_ls_wR_factor_ref         0.0933
_refine_ls_wR_factor_gt          0.0842
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.048
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_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 0.13336(18) 0.12812(6) 0.59356(11) 0.0277(2) Uani 1 1 d . . . . .
O2 O -0.01501(19) 0.04459(6) 0.76834(12) 0.0289(2) Uani 1 1 d . . . . .
O3 O 0.0307(2) 0.23871(6) -0.08106(13) 0.0345(3) Uani 1 1 d . . . . .
O4 O -0.2736(2) 0.20679(6) -0.24629(12) 0.0339(3) Uani 1 1 d . . . . .
N1 N 0.0606(2) 0.14985(7) 0.44669(14) 0.0269(3) Uani 1 1 d . . . . .
N2 N -0.1372(2) 0.10985(6) 0.41307(13) 0.0206(2) Uani 1 1 d . . . . .
N3 N -0.2123(2) 0.06266(7) 0.52072(14) 0.0242(3) Uani 1 1 d . . . . .
N4 N -0.1666(2) 0.20574(7) -0.11593(14) 0.0265(3) Uani 1 1 d . . . . .
C1 C -0.0397(3) 0.07301(8) 0.64147(16) 0.0240(3) Uani 1 1 d . . . . .
C2 C -0.2647(2) 0.11535(7) 0.26121(16) 0.0207(3) Uani 1 1 d . . . . .
C3 C -0.1579(2) 0.15996(7) 0.15062(15) 0.0218(3) Uani 1 1 d . . . . .
H3A H -0.0082 0.1878 0.1737 0.026 Uiso 1 1 calc R U . . .
C4 C -0.2815(2) 0.16154(8) 0.00536(16) 0.0229(3) Uani 1 1 d . . . . .
C5 C -0.5011(3) 0.12240(8) -0.03132(17) 0.0267(3) Uani 1 1 d . . . . .
H5A H -0.5813 0.1253 -0.1329 0.032 Uiso 1 1 calc R U . . .
C6 C -0.6019(3) 0.07882(8) 0.08318(17) 0.0273(3) Uani 1 1 d . . . . .
H6A H -0.7534 0.0518 0.0603 0.033 Uiso 1 1 calc R U . . .
C7 C -0.4830(2) 0.07436(8) 0.23093(17) 0.0240(3) Uani 1 1 d . . . . .
H7A H -0.5497 0.0439 0.3094 0.029 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 N1 1.3530(15) . ?
O1 C1 1.4206(17) . ?
O2 C1 1.1998(17) . ?
O3 N4 1.2263(16) . ?
O4 N4 1.2264(16) . ?
N1 N2 1.2891(16) . ?
N2 N3 1.3251(16) . ?
N2 C2 1.4379(17) . ?
N3 C1 1.3577(18) . ?
N4 C4 1.4695(18) . ?
C2 C7 1.3844(19) . ?
C2 C3 1.3859(19) . ?
C3 C4 1.3762(18) . ?
C3 H3A 0.9500 . ?
C4 C5 1.382(2) . ?
C5 C6 1.386(2) . ?
C5 H5A 0.9500 . ?
C6 C7 1.387(2) . ?
C6 H6A 0.9500 . ?
C7 H7A 0.9500 . ?

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 O1 C1 108.02(10) . . ?
N2 N1 O1 103.81(10) . . ?
N1 N2 N3 117.85(11) . . ?
N1 N2 C2 120.16(11) . . ?
N3 N2 C2 121.96(11) . . ?
N2 N3 C1 103.19(11) . . ?
O3 N4 O4 124.12(13) . . ?
O3 N4 C4 118.16(12) . . ?
O4 N4 C4 117.72(12) . . ?
O2 C1 N3 132.04(13) . . ?
O2 C1 O1 120.82(12) . . ?
N3 C1 O1 107.14(11) . . ?
C7 C2 C3 123.20(13) . . ?
C7 C2 N2 118.80(12) . . ?
C3 C2 N2 117.97(12) . . ?
C4 C3 C2 116.06(12) . . ?
C4 C3 H3A 122.0 . . ?
C2 C3 H3A 122.0 . . ?
C3 C4 C5 123.33(13) . . ?
C3 C4 N4 117.17(12) . . ?
C5 C4 N4 119.47(12) . . ?
C4 C5 C6 118.62(13) . . ?
C4 C5 H5A 120.7 . . ?
C6 C5 H5A 120.7 . . ?
C5 C6 C7 120.41(13) . . ?
C5 C6 H6A 119.8 . . ?
C7 C6 H6A 119.8 . . ?
C2 C7 C6 118.37(13) . . ?
C2 C7 H7A 120.8 . . ?
C6 C7 H7A 120.8 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 O1 N1 N2 -0.46(14) . . . . ?
O1 N1 N2 N3 0.40(15) . . . . ?
O1 N1 N2 C2 -177.67(11) . . . . ?
N1 N2 N3 C1 -0.16(15) . . . . ?
C2 N2 N3 C1 177.88(11) . . . . ?
N2 N3 C1 O2 -179.42(15) . . . . ?
N2 N3 C1 O1 -0.16(13) . . . . ?
N1 O1 C1 O2 179.76(12) . . . . ?
N1 O1 C1 N3 0.40(14) . . . . ?
N1 N2 C2 C7 -177.05(12) . . . . ?
N3 N2 C2 C7 4.96(18) . . . . ?
N1 N2 C2 C3 4.85(18) . . . . ?
N3 N2 C2 C3 -173.15(11) . . . . ?
C7 C2 C3 C4 -0.18(19) . . . . ?
N2 C2 C3 C4 177.83(11) . . . . ?
C2 C3 C4 C5 0.8(2) . . . . ?
C2 C3 C4 N4 -177.44(11) . . . . ?
O3 N4 C4 C3 -0.30(18) . . . . ?
O4 N4 C4 C3 179.15(12) . . . . ?
O3 N4 C4 C5 -178.61(12) . . . . ?
O4 N4 C4 C5 0.84(18) . . . . ?
C3 C4 C5 C6 -0.5(2) . . . . ?
N4 C4 C5 C6 177.71(12) . . . . ?
C4 C5 C6 C7 -0.5(2) . . . . ?
C3 C2 C7 C6 -0.7(2) . . . . ?
N2 C2 C7 C6 -178.70(12) . . . . ?
C5 C6 C7 C2 1.0(2) . . . . ?

_refine_diff_density_max         0.263
_refine_diff_density_min         -0.196
_refine_diff_density_rms         0.043

_shelxl_version_number           2014/6

####################################################################### 
# 
# 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_sh369
_database_code_depnum_ccdc_archive 'CCDC 1854066'
_audit_update_record             
;
2018-07-05 deposited with the CCDC.
2018-09-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 H4 N4 O2'
_chemical_formula_sum            'C6 H4 N4 O2'
_chemical_formula_weight         164.13

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                   3.7040(2)
_cell_length_b                   10.7498(5)
_cell_length_c                   17.5309(9)
_cell_angle_alpha                98.1710(10)
_cell_angle_beta                 94.5500(10)
_cell_angle_gamma                92.6580(10)
_cell_volume                     687.59(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    4663
_cell_measurement_theta_min      2.36
_cell_measurement_theta_max      31.09

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.586
_exptl_crystal_F_000             336
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.04
_exptl_absorpt_coefficient_mu    0.125
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10802
_diffrn_reflns_av_unetI/netI     0.0252
_diffrn_reflns_av_R_equivalents  0.0194
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         2.098
_diffrn_reflns_theta_max         31.118
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4436
_reflns_number_gt                3670
_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       'APEX (Bruker, 2009)'
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_reduction        'SAINT (Bruker, 2009)'
_computing_structure_solution    'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_publication_material  
'SHELXL-2014/6 (Sheldrick, 2014) and PLATON (Spek, 2009)'
_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)+(0.0609P)²+0.1243P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4436
_refine_ls_number_parameters     217
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0469
_refine_ls_R_factor_gt           0.0377
_refine_ls_wR_factor_ref         0.1080
_refine_ls_wR_factor_gt          0.1003
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_restrained_S_all      1.030
_refine_ls_shift/su_max          0.001
_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 0.0900(2) 0.94155(7) 0.41559(4) 0.02241(16) Uani 1 1 d . . . . .
O2 O 0.1075(2) 0.93961(8) 0.29202(4) 0.02743(18) Uani 1 1 d . . . . .
N1 N 0.6976(2) 1.36193(8) 0.53861(5) 0.02034(17) Uani 1 1 d . . . . .
N2 N 0.5589(2) 1.31974(8) 0.59311(5) 0.01923(17) Uani 1 1 d . . . . .
N3 N 0.4499(3) 1.29344(9) 0.64730(5) 0.0262(2) Uani 1 1 d . . . . .
N4 N 0.1724(2) 0.99052(8) 0.35940(5) 0.01661(16) Uani 1 1 d . . . . .
C1 C 0.6020(2) 1.29331(9) 0.46340(5) 0.01551(17) Uani 1 1 d . . . . .
C2 C 0.4269(2) 1.17374(8) 0.45021(5) 0.01423(17) Uani 1 1 d . . . . .
H2 H 0.3584 1.1326 0.4918 0.017 Uiso 1 1 calc R U . . .
C3 C 0.3565(2) 1.11702(8) 0.37376(5) 0.01429(17) Uani 1 1 d . . . . .
C4 C 0.4487(3) 1.17335(9) 0.31101(5) 0.01765(18) Uani 1 1 d . . . . .
H4 H 0.3942 1.1319 0.2595 0.021 Uiso 1 1 calc R U . . .
C5 C 0.6245(3) 1.29294(9) 0.32619(6) 0.01931(19) Uani 1 1 d . . . . .
H5 H 0.6912 1.3340 0.2844 0.023 Uiso 1 1 calc R U . . .
C6 C 0.7031(3) 1.35273(9) 0.40167(6) 0.01776(18) Uani 1 1 d . . . . .
H6 H 0.8252 1.4338 0.4114 0.021 Uiso 1 1 calc R U . . .
O1' O 0.4121(2) 0.69696(7) -0.13420(4) 0.02459(17) Uani 1 1 d . . . . .
O2' O 0.7678(2) 0.86619(7) -0.10341(4) 0.02456(17) Uani 1 1 d . . . . .
N1' N 0.1796(2) 0.54645(8) 0.11075(5) 0.01830(17) Uani 1 1 d . . . . .
N2' N 0.1296(2) 0.54113(8) 0.17973(5) 0.01879(17) Uani 1 1 d . . . . .
N3' N 0.0652(3) 0.52295(9) 0.23907(5) 0.0296(2) Uani 1 1 d . . . . .
N4' N 0.5760(2) 0.77900(8) -0.08633(5) 0.01672(16) Uani 1 1 d . . . . .
C1' C 0.3481(2) 0.66036(8) 0.09435(5) 0.01420(17) Uani 1 1 d . . . . .
C2' C 0.3779(2) 0.66551(8) 0.01616(5) 0.01437(17) Uani 1 1 d . . . . .
H2' H 0.2895 0.5972 -0.0222 0.017 Uiso 1 1 calc R U . . .
C3' C 0.5408(2) 0.77361(8) -0.00378(5) 0.01399(17) Uani 1 1 d . . . . .
C4' C 0.6729(2) 0.87629(9) 0.05043(5) 0.01554(17) Uani 1 1 d . . . . .
H4' H 0.7826 0.9492 0.0349 0.019 Uiso 1 1 calc R U . . .
C5' C 0.6389(3) 0.86866(9) 0.12790(5) 0.01647(18) Uani 1 1 d . . . . .
H5' H 0.7263 0.9375 0.1661 0.020 Uiso 1 1 calc R U . . .
C6' C 0.4783(3) 0.76145(9) 0.15062(5) 0.01568(17) Uani 1 1 d . . . . .
H6' H 0.4575 0.7571 0.2038 0.019 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 N4 1.2333(11) . ?
O2 N4 1.2295(10) . ?
N1 N2 1.2498(12) . ?
N1 C1 1.4259(12) . ?
N2 N3 1.1278(13) . ?
N4 C3 1.4720(12) . ?
C1 C2 1.3931(12) . ?
C1 C6 1.3993(13) . ?
C2 C3 1.3905(12) . ?
C2 H2 0.9500 . ?
C3 C4 1.3868(13) . ?
C4 C5 1.3946(14) . ?
C4 H4 0.9500 . ?
C5 C6 1.3886(14) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
O1' N4' 1.2288(11) . ?
O2' N4' 1.2346(11) . ?
N1' N2' 1.2467(11) . ?
N1' C1' 1.4245(12) . ?
N2' N3' 1.1270(12) . ?
N4' C3' 1.4723(12) . ?
C1' C2' 1.3925(12) . ?
C1' C6' 1.3992(12) . ?
C2' C3' 1.3857(13) . ?
C2' H2' 0.9500 . ?
C3' C4' 1.3925(12) . ?
C4' C5' 1.3874(13) . ?
C4' H4' 0.9500 . ?
C5' C6' 1.3946(13) . ?
C5' H5' 0.9500 . ?
C6' H6' 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 N1 C1 115.96(8) . . ?
N3 N2 N1 172.35(10) . . ?
O2 N4 O1 123.51(8) . . ?
O2 N4 C3 118.25(8) . . ?
O1 N4 C3 118.24(8) . . ?
C2 C1 C6 120.78(8) . . ?
C2 C1 N1 123.62(8) . . ?
C6 C1 N1 115.58(8) . . ?
C3 C2 C1 117.37(8) . . ?
C3 C2 H2 121.3 . . ?
C1 C2 H2 121.3 . . ?
C4 C3 C2 123.57(9) . . ?
C4 C3 N4 118.77(8) . . ?
C2 C3 N4 117.66(8) . . ?
C3 C4 C5 117.64(9) . . ?
C3 C4 H4 121.2 . . ?
C5 C4 H4 121.2 . . ?
C6 C5 C4 120.77(9) . . ?
C6 C5 H5 119.6 . . ?
C4 C5 H5 119.6 . . ?
C5 C6 C1 119.87(9) . . ?
C5 C6 H6 120.1 . . ?
C1 C6 H6 120.1 . . ?
N2' N1' C1' 116.70(8) . . ?
N3' N2' N1' 171.99(10) . . ?
O1' N4' O2' 123.81(8) . . ?
O1' N4' C3' 118.22(8) . . ?
O2' N4' C3' 117.97(8) . . ?
C2' C1' C6' 120.80(8) . . ?
C2' C1' N1' 114.87(8) . . ?
C6' C1' N1' 124.33(8) . . ?
C3' C2' C1' 117.82(8) . . ?
C3' C2' H2' 121.1 . . ?
C1' C2' H2' 121.1 . . ?
C2' C3' C4' 123.12(8) . . ?
C2' C3' N4' 118.01(8) . . ?
C4' C3' N4' 118.87(8) . . ?
C5' C4' C3' 117.82(8) . . ?
C5' C4' H4' 121.1 . . ?
C3' C4' H4' 121.1 . . ?
C4' C5' C6' 121.00(8) . . ?
C4' C5' H5' 119.5 . . ?
C6' C5' H5' 119.5 . . ?
C5' C6' C1' 119.45(8) . . ?
C5' C6' H6' 120.3 . . ?
C1' C6' H6' 120.3 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N2 N1 C1 C2 -12.56(14) . . . . ?
N2 N1 C1 C6 168.83(9) . . . . ?
C6 C1 C2 C3 -0.29(14) . . . . ?
N1 C1 C2 C3 -178.83(9) . . . . ?
C1 C2 C3 C4 -0.43(14) . . . . ?
C1 C2 C3 N4 179.83(8) . . . . ?
O2 N4 C3 C4 -0.02(13) . . . . ?
O1 N4 C3 C4 -179.64(9) . . . . ?
O2 N4 C3 C2 179.73(9) . . . . ?
O1 N4 C3 C2 0.11(13) . . . . ?
C2 C3 C4 C5 0.58(15) . . . . ?
N4 C3 C4 C5 -179.68(8) . . . . ?
C3 C4 C5 C6 -0.01(14) . . . . ?
C4 C5 C6 C1 -0.68(15) . . . . ?
C2 C1 C6 C5 0.83(14) . . . . ?
N1 C1 C6 C5 179.49(9) . . . . ?
N2' N1' C1' C2' -176.07(8) . . . . ?
N2' N1' C1' C6' 4.08(14) . . . . ?
C6' C1' C2' C3' 0.12(13) . . . . ?
N1' C1' C2' C3' -179.74(8) . . . . ?
C1' C2' C3' C4' -0.28(14) . . . . ?
C1' C2' C3' N4' 179.42(8) . . . . ?
O1' N4' C3' C2' 10.99(13) . . . . ?
O2' N4' C3' C2' -169.31(9) . . . . ?
O1' N4' C3' C4' -169.29(9) . . . . ?
O2' N4' C3' C4' 10.41(13) . . . . ?
C2' C3' C4' C5' 0.16(14) . . . . ?
N4' C3' C4' C5' -179.55(8) . . . . ?
C3' C4' C5' C6' 0.14(14) . . . . ?
C4' C5' C6' C1' -0.30(14) . . . . ?
C2' C1' C6' C5' 0.16(14) . . . . ?
N1' C1' C6' C5' 180.00(9) . . . . ?

_refine_diff_density_max         0.455
_refine_diff_density_min         -0.231
_refine_diff_density_rms         0.053

_shelxl_version_number           2014/6

####################################################################### 
# 
# 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_sh370
_database_code_depnum_ccdc_archive 'CCDC 1854065'
_audit_update_record             
;
2018-07-05 deposited with the CCDC.
2018-09-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 H4 N4 O2'
_chemical_formula_sum            'C6 H4 N4 O2'
_chemical_formula_weight         164.13

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

_cell_length_a                   3.6798(4)
_cell_length_b                   10.3754(10)
_cell_length_c                   18.1767(18)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     693.98(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    4362
_cell_measurement_theta_min      2.24
_cell_measurement_theta_max      30.19

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.571
_exptl_crystal_F_000             336
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.04
_exptl_absorpt_coefficient_mu    0.124
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13294
_diffrn_reflns_av_unetI/netI     0.0271
_diffrn_reflns_av_R_equivalents  0.0443
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         2.260
_diffrn_reflns_theta_max         30.228
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2066
_reflns_number_gt                1861
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.646
_reflns_Friedel_fraction_max     0.995
_reflns_Friedel_fraction_full    1.000

_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       'APEX (Bruker, 2009)'
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_reduction        'SAINT (Bruker, 2009)'
_computing_structure_solution    'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_publication_material  
'SHELXL-2014/6 (Sheldrick, 2014) and PLATON (Spek, 2009)'
_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)+(0.0510P)²+0.0593P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_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 694 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.6(6)
_chemical_absolute_configuration unk
_refine_ls_number_reflns         2066
_refine_ls_number_parameters     109
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0395
_refine_ls_R_factor_gt           0.0333
_refine_ls_wR_factor_ref         0.0875
_refine_ls_wR_factor_gt          0.0833
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_restrained_S_all      1.052
_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 0.9818(4) -0.19367(12) 0.18921(7) 0.0270(3) Uani 1 1 d . . . . .
O2 O 0.8676(4) 0.00905(12) 0.17041(7) 0.0309(3) Uani 1 1 d . . . . .
N1 N 0.3301(4) -0.05279(13) 0.49922(8) 0.0209(3) Uani 1 1 d . . . . .
N2 N 0.1856(4) 0.05071(13) 0.51919(7) 0.0203(3) Uani 1 1 d . . . . .
N3 N 0.0474(5) 0.13813(14) 0.54332(8) 0.0269(3) Uani 1 1 d . . . . .
N4 N 0.8641(4) -0.08791(13) 0.20951(8) 0.0201(3) Uani 1 1 d . . . . .
C1 C 0.4570(4) -0.05519(15) 0.42529(8) 0.0163(3) Uani 1 1 d . . . . .
C2 C 0.5959(5) -0.17335(14) 0.40113(9) 0.0185(3) Uani 1 1 d . . . . .
H2 H 0.5994 -0.2454 0.4334 0.022 Uiso 1 1 calc R U . . .
C3 C 0.7281(4) -0.18506(14) 0.33017(9) 0.0180(3) Uani 1 1 d . . . . .
H3 H 0.8241 -0.2647 0.3131 0.022 Uiso 1 1 calc R U . . .
C4 C 0.7175(4) -0.07770(14) 0.28429(9) 0.0160(3) Uani 1 1 d . . . . .
C5 C 0.5802(4) 0.04035(14) 0.30746(8) 0.0167(3) Uani 1 1 d . . . . .
H5 H 0.5758 0.1120 0.2749 0.020 Uiso 1 1 calc R U . . .
C6 C 0.4497(4) 0.05210(14) 0.37874(8) 0.0167(3) Uani 1 1 d . . . . .
H6 H 0.3565 0.1321 0.3957 0.020 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 N4 1.2361(17) . ?
O2 N4 1.2317(18) . ?
N1 N2 1.2520(19) . ?
N1 C1 1.423(2) . ?
N2 N3 1.129(2) . ?
N4 C4 1.466(2) . ?
C1 C6 1.399(2) . ?
C1 C2 1.399(2) . ?
C2 C3 1.384(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.392(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.390(2) . ?
C5 C6 1.387(2) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 N1 C1 115.35(13) . . ?
N3 N2 N1 173.37(16) . . ?
O2 N4 O1 123.31(14) . . ?
O2 N4 C4 118.67(13) . . ?
O1 N4 C4 118.01(13) . . ?
C6 C1 C2 120.97(14) . . ?
C6 C1 N1 123.45(14) . . ?
C2 C1 N1 115.58(13) . . ?
C3 C2 C1 119.87(14) . . ?
C3 C2 H2 120.1 . . ?
C1 C2 H2 120.1 . . ?
C2 C3 C4 118.57(13) . . ?
C2 C3 H3 120.7 . . ?
C4 C3 H3 120.7 . . ?
C5 C4 C3 122.26(14) . . ?
C5 C4 N4 118.56(13) . . ?
C3 C4 N4 119.16(13) . . ?
C6 C5 C4 119.08(13) . . ?
C6 C5 H5 120.5 . . ?
C4 C5 H5 120.5 . . ?
C5 C6 C1 119.25(13) . . ?
C5 C6 H6 120.4 . . ?
C1 C6 H6 120.4 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N2 N1 C1 C6 4.7(2) . . . . ?
N2 N1 C1 C2 -175.79(14) . . . . ?
C6 C1 C2 C3 -0.1(2) . . . . ?
N1 C1 C2 C3 -179.58(14) . . . . ?
C1 C2 C3 C4 -0.3(2) . . . . ?
C2 C3 C4 C5 0.2(2) . . . . ?
C2 C3 C4 N4 178.65(14) . . . . ?
O2 N4 C4 C5 1.5(2) . . . . ?
O1 N4 C4 C5 -179.22(14) . . . . ?
O2 N4 C4 C3 -176.95(16) . . . . ?
O1 N4 C4 C3 2.3(2) . . . . ?
C3 C4 C5 C6 0.1(2) . . . . ?
N4 C4 C5 C6 -178.29(14) . . . . ?
C4 C5 C6 C1 -0.5(2) . . . . ?
C2 C1 C6 C5 0.4(2) . . . . ?
N1 C1 C6 C5 179.91(15) . . . . ?

_refine_diff_density_max         0.275
_refine_diff_density_min         -0.180
_refine_diff_density_rms         0.045

_shelxl_version_number           2014/6

####################################################################### 
# 
# 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_sh344
_database_code_depnum_ccdc_archive 'CCDC 1854062'
_audit_update_record             
;
2018-07-05 deposited with the CCDC.
2018-09-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C7 H3 N5 O6'
_chemical_formula_sum            'C7 H3 N5 O6'
_chemical_formula_weight         253.14

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           29
_space_group_name_H-M_alt        'P c a 21'
_space_group_name_Hall           'P 2c -2ac'

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

_cell_length_a                   9.893(3)
_cell_length_b                   18.586(6)
_cell_length_c                   9.943(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1828.2(10)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2458
_cell_measurement_theta_min      2.19
_cell_measurement_theta_max      22.15

_exptl_crystal_description       needle
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.839
_exptl_crystal_F_000             1024
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.01
_exptl_crystal_size_min          0.01
_exptl_absorpt_coefficient_mu    0.164
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            26673
_diffrn_reflns_av_unetI/netI     0.0760
_diffrn_reflns_av_R_equivalents  0.1133
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         1.096
_diffrn_reflns_theta_max         28.275
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4496
_reflns_number_gt                2655
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.877
_reflns_Friedel_fraction_max     0.985
_reflns_Friedel_fraction_full    1.000

_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       'APEX (Bruker, 2009)'
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_reduction        'SAINT (Bruker, 2009)'
_computing_structure_solution    'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_publication_material  
'SHELXL-2014/6 (Sheldrick, 2014) and PLATON (Spek, 2009)'
_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)+(0.0494P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_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 904 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   1.4(10)
_chemical_absolute_configuration unk
_refine_ls_number_reflns         4496
_refine_ls_number_parameters     464
_refine_ls_number_restraints     13
_refine_ls_R_factor_all          0.1138
_refine_ls_R_factor_gt           0.0566
_refine_ls_wR_factor_ref         0.1275
_refine_ls_wR_factor_gt          0.1061
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_restrained_S_all      1.043
_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
N1 N 0.4783(5) 0.8000(2) 1.1942(4) 0.0557(13) Uani 1 1 d . . . . .
N2 N 0.5359(4) 0.8570(2) 1.1496(4) 0.0427(11) Uani 1 1 d . . . . .
N3 N 0.6040(4) 0.8979(2) 1.2345(4) 0.0461(11) Uani 1 1 d . . . . .
N4 N 0.3535(5) 0.8066(2) 0.7059(4) 0.0457(11) Uani 1 1 d . . . . .
N5 N 0.6510(4) 1.0126(2) 0.7763(4) 0.0424(10) Uani 1 1 d . . . . .
O1 O 0.5095(4) 0.8003(2) 1.3262(4) 0.0687(14) Uani 1 1 d . . . . .
O2 O 0.6343(4) 0.8734(2) 1.4635(4) 0.0685(13) Uani 1 1 d . . . . .
O3 O 0.3058(4) 0.7516(2) 0.7526(4) 0.0531(10) Uani 1 1 d . . . . .
O4 O 0.3376(4) 0.8268(2) 0.5908(3) 0.0504(10) Uani 1 1 d . . . . .
O5 O 0.6624(4) 1.01923(18) 0.6540(3) 0.0464(9) Uani 1 1 d . . . . .
O6 O 0.6932(4) 1.0563(2) 0.8575(4) 0.0587(11) Uani 1 1 d . . . . .
C1 C 0.5912(6) 0.8620(3) 1.3532(6) 0.0561(16) Uani 1 1 d . . . . .
C2 C 0.5247(5) 0.8748(3) 1.0093(5) 0.0357(11) Uani 1 1 d . . . . .
C3 C 0.4460(5) 0.8319(3) 0.9288(5) 0.0398(13) Uani 1 1 d . . . . .
H3A H 0.3993 0.7912 0.9633 0.048 Uiso 1 1 calc R U . . .
C4 C 0.4385(5) 0.8510(3) 0.7947(5) 0.0373(12) Uani 1 1 d . . . . .
C5 C 0.5045(5) 0.9091(2) 0.7414(5) 0.0354(11) Uani 1 1 d . . . . .
H5A H 0.4979 0.9208 0.6487 0.042 Uiso 1 1 calc R U . . .
C6 C 0.5807(5) 0.9495(3) 0.8284(5) 0.0342(11) Uani 1 1 d . . . . .
C7 C 0.5930(5) 0.9340(3) 0.9637(5) 0.0359(11) Uani 1 1 d . . . . .
H7A H 0.6461 0.9629 1.0221 0.043 Uiso 1 1 calc R U . . .
O1' O 1.2970(17) 0.2702(7) 0.5870(16) 0.051(3) Uani 0.468(5) 1 d . . P A 1
O2' O 1.2190(8) 0.2227(4) 0.7726(8) 0.048(2) Uani 0.468(5) 1 d . . P A 1
N1' N 1.2484(17) 0.3076(8) 0.4743(12) 0.050(3) Uani 0.468(5) 1 d . . P A 1
N2' N 1.1205(16) 0.3161(8) 0.5087(16) 0.036(4) Uani 0.468(5) 1 d . . P A 1
N3' N 1.083(3) 0.2862(14) 0.6201(19) 0.044(5) Uani 0.468(5) 1 d . . P A 1
C1' C 1.1976(16) 0.2552(7) 0.6746(14) 0.040(3) Uani 0.468(5) 1 d . . P A 1
C2' C 1.0342(8) 0.3534(5) 0.4255(8) 0.031(3) Uani 0.468(5) 1 d G . P A 1
C3' C 0.8955(8) 0.3507(6) 0.4472(8) 0.031(3) Uani 0.468(5) 1 d G . P A 1
H3'A H 0.8604 0.3245 0.5214 0.037 Uiso 0.468(5) 1 calc R U P A 1
C4' C 0.8083(7) 0.3865(6) 0.3604(10) 0.033(4) Uani 0.468(5) 1 d G . P A 1
C5' C 0.8597(8) 0.4249(5) 0.2519(9) 0.032(3) Uani 0.468(5) 1 d G . P A 1
H5'A H 0.8000 0.4493 0.1926 0.039 Uiso 0.468(5) 1 calc R U P A 1
C6' C 0.9984(9) 0.4275(4) 0.2302(7) 0.037(3) Uani 0.468(5) 1 d G . P A 1
C7' C 1.0857(7) 0.3917(5) 0.3170(8) 0.024(3) Uani 0.468(5) 1 d G . P A 1
H7'A H 1.1805 0.3935 0.3021 0.028 Uiso 0.468(5) 1 calc R U P A 1
N4' N 0.6670(19) 0.3833(11) 0.380(2) 0.038(4) Uani 0.468(5) 1 d . . P A 1
O3' O 0.627(2) 0.3493(17) 0.479(3) 0.043(5) Uani 0.468(5) 1 d . . P A 1
O4' O 0.5943(15) 0.4138(11) 0.299(2) 0.052(4) Uani 0.468(5) 1 d . . P A 1
N5' N 1.060(3) 0.4631(9) 0.1194(19) 0.036(4) Uani 0.468(5) 1 d . . P A 1
O5' O 0.9706(12) 0.4968(6) 0.0447(12) 0.050(3) Uani 0.468(5) 1 d . . P A 1
O6' O 1.1784(16) 0.4625(6) 0.0972(11) 0.050(3) Uani 0.468(5) 1 d . . P A 1
O1" O 0.5400(11) 0.3527(5) 0.4682(10) 0.054(2) Uani 0.532(5) 1 d . . P A 2
O2" O 0.4231(10) 0.4109(4) 0.3002(9) 0.068(3) Uani 0.532(5) 1 d . . P A 2
N1" N 0.669(2) 0.346(2) 0.497(4) 0.046(6) Uani 0.532(5) 1 d . U P A 2
N2" N 0.7292(16) 0.3781(10) 0.4010(18) 0.042(4) Uani 0.532(5) 1 d . . P A 2
N3" N 0.6545(19) 0.4114(10) 0.309(3) 0.055(5) Uani 0.532(5) 1 d . . P A 2
C1" C 0.532(2) 0.3966(8) 0.3449(15) 0.055(4) Uani 0.532(5) 1 d . . P A 2
C2" C 1.0889(11) 0.3421(6) 0.4671(12) 0.069(7) Uani 0.532(5) 1 d G . P A 2
C3" C 0.9491(11) 0.3427(5) 0.4804(9) 0.056(4) Uani 0.532(5) 1 d G . P A 2
H3"A H 0.9073 0.3178 0.5527 0.067 Uiso 0.532(5) 1 calc R U P A 2
C4" C 0.8702(8) 0.3798(5) 0.3877(10) 0.038(3) Uani 0.532(5) 1 d G . P A 2
C5" C 0.9313(12) 0.4163(5) 0.2818(9) 0.062(4) Uani 0.532(5) 1 d G . P A 2
H5"A H 0.8774 0.4416 0.2185 0.074 Uiso 0.532(5) 1 calc R U P A 2
C6" C 1.0711(13) 0.4157(5) 0.2686(11) 0.065(5) Uani 0.532(5) 1 d G . P A 2
C7" C 1.1500(9) 0.3786(6) 0.3613(14) 0.078(5) Uani 0.532(5) 1 d G . P A 2
H7"A H 1.2456 0.3782 0.3523 0.094 Uiso 0.532(5) 1 calc R U P A 2
N4" N 1.169(2) 0.3032(9) 0.557(2) 0.070(5) Uani 0.532(5) 1 d . . P A 2
O3" O 1.111(3) 0.2706(12) 0.6533(19) 0.078(6) Uani 0.532(5) 1 d . . P A 2
O4" O 1.291(2) 0.3002(10) 0.549(2) 0.089(5) Uani 0.532(5) 1 d . . P A 2
N5" N 1.1332(19) 0.4533(9) 0.1521(19) 0.073(5) Uani 0.532(5) 1 d . U P A 2
O5" O 1.051(3) 0.4852(9) 0.0836(19) 0.081(7) Uani 0.532(5) 1 d . . P A 2
O6" O 1.259(2) 0.4425(9) 0.151(2) 0.140(6) Uani 0.532(5) 1 d . . P A 2


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 N2 1.282(5) . ?
N1 O1 1.348(6) . ?
N2 N3 1.320(6) . ?
N2 C2 1.438(6) . ?
N3 C1 1.362(7) . ?
N4 O4 1.215(5) . ?
N4 O3 1.218(5) . ?
N4 C4 1.473(6) . ?
N5 O6 1.219(5) . ?
N5 O5 1.228(5) . ?
N5 C6 1.458(6) . ?
O1 C1 1.428(7) . ?
O2 C1 1.196(7) . ?
C2 C7 1.368(7) . ?
C2 C3 1.373(7) . ?
C3 C4 1.382(6) . ?
C3 H3A 0.9500 . ?
C4 C5 1.367(7) . ?
C5 C6 1.371(7) . ?
C5 H5A 0.9500 . ?
C6 C7 1.382(7) . ?
C7 H7A 0.9500 . ?
O1' C1' 1.34(2) . ?
O1' N1' 1.403(18) . ?
O2' C1' 1.166(16) . ?
N1' N2' 1.32(3) . ?
N2' N3' 1.29(3) . ?
N2' C2' 1.375(14) . ?
N3' C1' 1.38(2) . ?
C2' C3' 1.3900 . ?
C2' C7' 1.3900 . ?
C3' C4' 1.3900 . ?
C3' H3'A 0.9500 . ?
C4' C5' 1.3900 . ?
C4' N4' 1.41(2) . ?
C5' C6' 1.3900 . ?
C5' H5'A 0.9500 . ?
C6' C7' 1.3900 . ?
C6' N5' 1.42(2) . ?
C7' H7'A 0.9500 . ?
N4' O4' 1.22(2) . ?
N4' O3' 1.23(4) . ?
N5' O6' 1.19(3) . ?
N5' O5' 1.32(3) . ?
O1" N1" 1.31(2) . ?
O1" C1" 1.475(17) . ?
O2" C1" 1.191(18) . ?
N1" N2" 1.28(4) . ?
N2" N3" 1.33(2) . ?
N2" C4" 1.402(16) . ?
N3" C1" 1.30(3) . ?
C2" C3" 1.3900 . ?
C2" C7" 1.3900 . ?
C2" N4" 1.394(18) . ?
C3" C4" 1.3900 . ?
C3" H3"A 0.9500 . ?
C4" C5" 1.3900 . ?
C5" C6" 1.3900 . ?
C5" H5"A 0.9500 . ?
C6" C7" 1.3900 . ?
C6" N5" 1.49(2) . ?
C7" H7"A 0.9500 . ?
N4" O4" 1.21(3) . ?
N4" O3" 1.27(3) . ?
N5" O5" 1.22(3) . ?
N5" O6" 1.26(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
N2 N1 O1 103.4(4) . . ?
N1 N2 N3 118.8(4) . . ?
N1 N2 C2 119.4(4) . . ?
N3 N2 C2 121.8(4) . . ?
N2 N3 C1 102.9(4) . . ?
O4 N4 O3 124.7(4) . . ?
O4 N4 C4 117.7(4) . . ?
O3 N4 C4 117.6(4) . . ?
O6 N5 O5 123.9(4) . . ?
O6 N5 C6 117.7(4) . . ?
O5 N5 C6 118.4(4) . . ?
N1 O1 C1 108.4(4) . . ?
O2 C1 N3 132.4(5) . . ?
O2 C1 O1 121.1(5) . . ?
N3 C1 O1 106.5(5) . . ?
C7 C2 C3 123.6(4) . . ?
C7 C2 N2 117.9(4) . . ?
C3 C2 N2 118.4(4) . . ?
C2 C3 C4 116.3(4) . . ?
C2 C3 H3A 121.8 . . ?
C4 C3 H3A 121.8 . . ?
C5 C4 C3 123.5(5) . . ?
C5 C4 N4 118.9(4) . . ?
C3 C4 N4 117.7(4) . . ?
C4 C5 C6 116.8(5) . . ?
C4 C5 H5A 121.6 . . ?
C6 C5 H5A 121.6 . . ?
C5 C6 C7 123.2(4) . . ?
C5 C6 N5 118.6(4) . . ?
C7 C6 N5 118.1(4) . . ?
C2 C7 C6 116.6(5) . . ?
C2 C7 H7A 121.7 . . ?
C6 C7 H7A 121.7 . . ?
C1' O1' N1' 111.7(15) . . ?
N2' N1' O1' 100.4(14) . . ?
N3' N2' N1' 116.5(15) . . ?
N3' N2' C2' 123.5(17) . . ?
N1' N2' C2' 119.9(13) . . ?
N2' N3' C1' 106(2) . . ?
O2' C1' O1' 121.1(15) . . ?
O2' C1' N3' 133.8(14) . . ?
O1' C1' N3' 105.1(15) . . ?
N2' C2' C3' 120.1(9) . . ?
N2' C2' C7' 119.9(9) . . ?
C3' C2' C7' 120.0 . . ?
C4' C3' C2' 120.0 . . ?
C4' C3' H3'A 120.0 . . ?
C2' C3' H3'A 120.0 . . ?
C5' C4' C3' 120.0 . . ?
C5' C4' N4' 119.5(10) . . ?
C3' C4' N4' 120.5(10) . . ?
C6' C5' C4' 120.0 . . ?
C6' C5' H5'A 120.0 . . ?
C4' C5' H5'A 120.0 . . ?
C5' C6' C7' 120.0 . . ?
C5' C6' N5' 124.1(12) . . ?
C7' C6' N5' 115.8(12) . . ?
C6' C7' C2' 120.0 . . ?
C6' C7' H7'A 120.0 . . ?
C2' C7' H7'A 120.0 . . ?
O4' N4' O3' 125(2) . . ?
O4' N4' C4' 118(2) . . ?
O3' N4' C4' 117.0(16) . . ?
O6' N5' O5' 124.2(15) . . ?
O6' N5' C6' 124.2(19) . . ?
O5' N5' C6' 112(2) . . ?
N1" O1" C1" 107(2) . . ?
N2" N1" O1" 104(2) . . ?
N1" N2" N3" 118.2(18) . . ?
N1" N2" C4" 123.3(17) . . ?
N3" N2" C4" 118.5(16) . . ?
C1" N3" N2" 103.5(17) . . ?
O2" C1" N3" 134.0(17) . . ?
O2" C1" O1" 119.0(16) . . ?
N3" C1" O1" 107.0(14) . . ?
C3" C2" C7" 120.0 . . ?
C3" C2" N4" 120.7(14) . . ?
C7" C2" N4" 119.3(14) . . ?
C2" C3" C4" 120.0 . . ?
C2" C3" H3"A 120.0 . . ?
C4" C3" H3"A 120.0 . . ?
C5" C4" C3" 120.0 . . ?
C5" C4" N2" 121.0(11) . . ?
C3" C4" N2" 119.0(11) . . ?
C4" C5" C6" 120.0 . . ?
C4" C5" H5"A 120.0 . . ?
C6" C5" H5"A 120.0 . . ?
C7" C6" C5" 120.0 . . ?
C7" C6" N5" 121.2(13) . . ?
C5" C6" N5" 118.7(13) . . ?
C6" C7" C2" 120.0 . . ?
C6" C7" H7"A 120.0 . . ?
C2" C7" H7"A 120.0 . . ?
O4" N4" O3" 118(2) . . ?
O4" N4" C2" 123(2) . . ?
O3" N4" C2" 118(2) . . ?
O5" N5" O6" 137(3) . . ?
O5" N5" C6" 113(2) . . ?
O6" N5" C6" 110(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 N1 N2 N3 -0.2(7) . . . . ?
O1 N1 N2 C2 179.8(4) . . . . ?
N1 N2 N3 C1 1.0(7) . . . . ?
C2 N2 N3 C1 -179.0(5) . . . . ?
N2 N1 O1 C1 -0.7(6) . . . . ?
N2 N3 C1 O2 178.5(7) . . . . ?
N2 N3 C1 O1 -1.3(6) . . . . ?
N1 O1 C1 O2 -178.5(6) . . . . ?
N1 O1 C1 N3 1.3(7) . . . . ?
N1 N2 C2 C7 -176.7(5) . . . . ?
N3 N2 C2 C7 3.3(7) . . . . ?
N1 N2 C2 C3 3.5(7) . . . . ?
N3 N2 C2 C3 -176.4(5) . . . . ?
C7 C2 C3 C4 0.3(8) . . . . ?
N2 C2 C3 C4 -180.0(4) . . . . ?
C2 C3 C4 C5 0.2(8) . . . . ?
C2 C3 C4 N4 -179.2(4) . . . . ?
O4 N4 C4 C5 -5.5(7) . . . . ?
O3 N4 C4 C5 173.4(5) . . . . ?
O4 N4 C4 C3 173.9(5) . . . . ?
O3 N4 C4 C3 -7.2(7) . . . . ?
C3 C4 C5 C6 -0.4(7) . . . . ?
N4 C4 C5 C6 179.0(4) . . . . ?
C4 C5 C6 C7 0.1(7) . . . . ?
C4 C5 C6 N5 -178.9(4) . . . . ?
O6 N5 C6 C5 164.3(4) . . . . ?
O5 N5 C6 C5 -14.6(7) . . . . ?
O6 N5 C6 C7 -14.8(7) . . . . ?
O5 N5 C6 C7 166.3(4) . . . . ?
C3 C2 C7 C6 -0.5(7) . . . . ?
N2 C2 C7 C6 179.7(4) . . . . ?
C5 C6 C7 C2 0.3(7) . . . . ?
N5 C6 C7 C2 179.4(4) . . . . ?
C1' O1' N1' N2' 3.8(17) . . . . ?
O1' N1' N2' N3' -4(2) . . . . ?
O1' N1' N2' C2' 178.0(15) . . . . ?
N1' N2' N3' C1' 3(3) . . . . ?
C2' N2' N3' C1' -179.3(16) . . . . ?
N1' O1' C1' O2' 178.0(12) . . . . ?
N1' O1' C1' N3' -2(2) . . . . ?
N2' N3' C1' O2' 179.5(14) . . . . ?
N2' N3' C1' O1' 0(2) . . . . ?
N3' N2' C2' C3' -10(2) . . . . ?
N1' N2' C2' C3' 167.5(11) . . . . ?
N3' N2' C2' C7' 171.7(17) . . . . ?
N1' N2' C2' C7' -10(2) . . . . ?
N2' C2' C3' C4' -177.9(13) . . . . ?
C7' C2' C3' C4' 0.0 . . . . ?
C2' C3' C4' C5' 0.0 . . . . ?
C2' C3' C4' N4' 179.1(13) . . . . ?
C3' C4' C5' C6' 0.0 . . . . ?
N4' C4' C5' C6' -179.1(13) . . . . ?
C4' C5' C6' C7' 0.0 . . . . ?
C4' C5' C6' N5' 177.6(13) . . . . ?
C5' C6' C7' C2' 0.0 . . . . ?
N5' C6' C7' C2' -177.8(11) . . . . ?
N2' C2' C7' C6' 177.9(13) . . . . ?
C3' C2' C7' C6' 0.0 . . . . ?
C5' C4' N4' O4' 1(2) . . . . ?
C3' C4' N4' O4' -177.7(15) . . . . ?
C5' C4' N4' O3' -179.2(19) . . . . ?
C3' C4' N4' O3' 2(3) . . . . ?
C5' C6' N5' O6' -176.3(14) . . . . ?
C7' C6' N5' O6' 1(2) . . . . ?
C5' C6' N5' O5' 4(2) . . . . ?
C7' C6' N5' O5' -178.4(12) . . . . ?
C1" O1" N1" N2" -3(3) . . . . ?
O1" N1" N2" N3" 4(4) . . . . ?
O1" N1" N2" C4" -175.7(17) . . . . ?
N1" N2" N3" C1" -3(3) . . . . ?
C4" N2" N3" C1" 176.5(14) . . . . ?
N2" N3" C1" O2" -179.0(17) . . . . ?
N2" N3" C1" O1" 1(2) . . . . ?
N1" O1" C1" O2" -179(2) . . . . ?
N1" O1" C1" N3" 1(3) . . . . ?
C7" C2" C3" C4" 0.0 . . . . ?
N4" C2" C3" C4" -177.9(12) . . . . ?
C2" C3" C4" C5" 0.0 . . . . ?
C2" C3" C4" N2" 178.3(11) . . . . ?
N1" N2" C4" C5" -179(2) . . . . ?
N3" N2" C4" C5" 1(2) . . . . ?
N1" N2" C4" C3" 3(3) . . . . ?
N3" N2" C4" C3" -177.4(14) . . . . ?
C3" C4" C5" C6" 0.0 . . . . ?
N2" C4" C5" C6" -178.3(11) . . . . ?
C4" C5" C6" C7" 0.0 . . . . ?
C4" C5" C6" N5" 178.1(10) . . . . ?
C5" C6" C7" C2" 0.0 . . . . ?
N5" C6" C7" C2" -178.1(10) . . . . ?
C3" C2" C7" C6" 0.0 . . . . ?
N4" C2" C7" C6" 177.9(12) . . . . ?
C3" C2" N4" O4" 179.0(14) . . . . ?
C7" C2" N4" O4" 1(2) . . . . ?
C3" C2" N4" O3" -3(2) . . . . ?
C7" C2" N4" O3" 179.6(14) . . . . ?
C7" C6" N5" O5" -177.4(14) . . . . ?
C5" C6" N5" O5" 4.5(19) . . . . ?
C7" C6" N5" O6" 2.9(15) . . . . ?
C5" C6" N5" O6" -175.2(10) . . . . ?

_refine_diff_density_max         0.203
_refine_diff_density_min         -0.180
_refine_diff_density_rms         0.045

_shelxl_version_number           2014/6

####################################################################### 
# 
# 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_d05
_database_code_depnum_ccdc_archive 'CCDC 1854064'
_audit_update_record             
;
2018-07-05 deposited with the CCDC.
2018-09-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C7 H5 N5 O2'
_chemical_formula_sum            'C7 H5 N5 O2'
_chemical_formula_weight         191.16

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                   11.1512(5)
_cell_length_b                   17.2780(7)
_cell_length_c                   12.9735(5)
_cell_angle_alpha                90
_cell_angle_beta                 106.2590(10)
_cell_angle_gamma                90
_cell_volume                     2399.64(17)
_cell_formula_units_Z            12
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9893
_cell_measurement_theta_min      2.24
_cell_measurement_theta_max      28.48

_exptl_crystal_description       needle
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.587
_exptl_crystal_F_000             1176
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.04
_exptl_absorpt_coefficient_mu    0.123
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            47363
_diffrn_reflns_av_unetI/netI     0.0243
_diffrn_reflns_av_R_equivalents  0.0419
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.016
_diffrn_reflns_theta_max         28.963
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             6343
_reflns_number_gt                5010
_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       'APEX (Bruker, 2009)'
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_reduction        'SAINT (Bruker, 2009)'
_computing_structure_solution    'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_publication_material  
'SHELXL-2014/6 (Sheldrick, 2014) and PLATON (Spek, 2009)'
_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)+(0.0193P)²+2.0805P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6343
_refine_ls_number_parameters     506
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0716
_refine_ls_R_factor_gt           0.0528
_refine_ls_wR_factor_ref         0.1187
_refine_ls_wR_factor_gt          0.1108
_refine_ls_goodness_of_fit_ref   1.158
_refine_ls_restrained_S_all      1.158
_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 0.37542(14) -0.10149(8) 0.50650(12) 0.0382(3) Uani 1 1 d . . . . .
O2 O 0.22556(14) -0.11980(8) 0.36060(12) 0.0386(4) Uani 1 1 d . . . . .
N1 N 0.02574(14) 0.13481(8) 0.25835(12) 0.0238(3) Uani 1 1 d . . . . .
N2 N -0.04158(14) 0.08599(9) 0.18185(12) 0.0274(3) Uani 1 1 d . . . . .
N3 N -0.12566(15) 0.12727(10) 0.11804(13) 0.0312(4) Uani 1 1 d . . . . .
N4 N -0.11847(16) 0.20297(9) 0.14929(14) 0.0337(4) Uani 1 1 d . . . . .
N5 N 0.28962(15) -0.07798(9) 0.43197(13) 0.0281(3) Uani 1 1 d . . . . .
C1 C 0.13188(16) 0.10823(10) 0.34102(14) 0.0220(3) Uani 1 1 d . . . . .
C2 C 0.15759(16) 0.02976(10) 0.34652(14) 0.0223(3) Uani 1 1 d . . . . .
H2 H 0.1065 -0.0058 0.2976 0.027 Uiso 1 1 calc R U . . .
C3 C 0.26064(16) 0.00556(10) 0.42610(14) 0.0226(3) Uani 1 1 d . . . . .
C4 C 0.33848(17) 0.05470(11) 0.49865(15) 0.0261(4) Uani 1 1 d . . . . .
H4 H 0.4084 0.0354 0.5526 0.031 Uiso 1 1 calc R U . . .
C5 C 0.31127(18) 0.13319(11) 0.49027(15) 0.0286(4) Uani 1 1 d . . . . .
H5 H 0.3634 0.1685 0.5388 0.034 Uiso 1 1 calc R U . . .
C6 C 0.20771(17) 0.16067(10) 0.41097(15) 0.0264(4) Uani 1 1 d . . . . .
H6 H 0.1894 0.2145 0.4050 0.032 Uiso 1 1 calc R U . . .
C7 C -0.02388(19) 0.20564(11) 0.23611(16) 0.0323(4) Uani 1 1 d . . . . .
H7 H 0.0051 0.2509 0.2771 0.039 Uiso 1 1 calc R U . . .
O1' O -0.03454(14) 0.08572(8) -0.11493(12) 0.0377(3) Uani 1 1 d . . . . .
O2' O -0.02638(15) 0.20996(8) -0.09816(14) 0.0481(4) Uani 1 1 d . . . . .
C1' C 0.28191(16) 0.05839(10) 0.13331(14) 0.0227(3) Uani 1 1 d . . . . .
C2' C 0.17561(16) 0.06434(10) 0.04696(14) 0.0230(3) Uani 1 1 d . . . . .
H2' H 0.1383 0.0200 0.0076 0.028 Uiso 1 1 calc R U . . .
C3' C 0.12619(16) 0.13758(10) 0.02062(14) 0.0237(4) Uani 1 1 d . . . . .
C4' C 0.17758(18) 0.20379(10) 0.07629(15) 0.0276(4) Uani 1 1 d . . . . .
H4' H 0.1421 0.2533 0.0556 0.033 Uiso 1 1 calc R U . . .
C5' C 0.28268(18) 0.19510(11) 0.16332(15) 0.0285(4) Uani 1 1 d . . . . .
H5' H 0.3188 0.2394 0.2036 0.034 Uiso 1 1 calc R U . . .
C6' C 0.33553(17) 0.12320(10) 0.19230(15) 0.0260(4) Uani 1 1 d . . . . .
H6' H 0.4076 0.1180 0.2518 0.031 Uiso 1 1 calc R U . . .
C7' C 0.31785(18) -0.08409(11) 0.11027(15) 0.0291(4) Uani 1 1 d . . . . .
H7' H 0.2616 -0.0926 0.0412 0.035 Uiso 1 1 calc R U . . .
N1' N 0.33655(13) -0.01585(9) 0.16269(12) 0.0235(3) Uani 1 1 d . . . . .
N2' N 0.42433(15) -0.02742(10) 0.25831(13) 0.0298(3) Uani 1 1 d . . . . .
N3' N 0.45456(16) -0.09988(10) 0.26145(13) 0.0339(4) Uani 1 1 d . . . . .
N4' N 0.38933(16) -0.13676(10) 0.16943(13) 0.0347(4) Uani 1 1 d . . . . .
N5' N 0.01382(15) 0.14522(9) -0.07111(13) 0.0291(3) Uani 1 1 d . . . . .
O1A O 0.4171(9) -0.0907(5) 0.8862(7) 0.0326(15) Uani 0.504(3) 1 d . . P A 1
O2A O 0.3099(5) -0.1089(3) 0.7270(4) 0.0511(10) Uani 0.504(3) 1 d . . P A 1
N1A N 0.0817(11) 0.1398(6) 0.6260(10) 0.036(3) Uani 0.504(3) 1 d . . P A 1
N2A N 0.0078(4) 0.0869(2) 0.5502(4) 0.0381(9) Uani 0.504(3) 1 d . . P A 1
N3A N -0.0469(19) 0.2060(12) 0.4978(18) 0.038(2) Uani 0.504(3) 1 d . . P A 1
N4A N -0.0675(6) 0.1285(3) 0.4776(6) 0.0445(13) Uani 0.504(3) 1 d . . P A 1
N5A N 0.3499(4) -0.0698(3) 0.8055(3) 0.0386(9) Uani 0.504(3) 1 d . . P A 1
C1A C 0.1779(4) 0.1121(3) 0.7099(4) 0.0353(10) Uani 0.504(3) 1 d . . P A 1
C2A C 0.2134(4) 0.0360(3) 0.7128(4) 0.0314(10) Uani 0.504(3) 1 d . . P A 1
H2A H 0.1753 0.0030 0.6542 0.038 Uiso 0.504(3) 1 calc R U P A 1
C3A C 0.293(2) 0.0099(13) 0.7896(14) 0.037(3) Uani 0.504(3) 1 d . . P A 1
C4A C 0.3665(4) 0.0600(3) 0.8841(3) 0.0384(11) Uani 0.504(3) 1 d . . P A 1
H4A H 0.4315 0.0400 0.9419 0.046 Uiso 0.504(3) 1 calc R U P A 1
C5A C 0.3298(5) 0.1363(3) 0.8780(4) 0.0435(12) Uani 0.504(3) 1 d . . P A 1
H5A H 0.3698 0.1711 0.9338 0.052 Uiso 0.504(3) 1 calc R U P A 1
C6A C 0.2353(7) 0.1632(4) 0.7916(6) 0.0376(14) Uani 0.504(3) 1 d . . P A 1
H6A H 0.2100 0.2159 0.7882 0.045 Uiso 0.504(3) 1 calc R U P A 1
C7A C 0.0456(5) 0.2104(3) 0.5841(4) 0.0472(12) Uani 0.504(3) 1 d . . P A 1
H7A H 0.0834 0.2575 0.6143 0.057 Uiso 0.504(3) 1 calc R U P A 1
O1B O -0.0614(4) 0.0901(3) 0.4856(4) 0.0378(9) Uani 0.496(3) 1 d . . P A 2
O2B O -0.0592(18) 0.2160(11) 0.4970(18) 0.061(5) Uani 0.496(3) 1 d . . P A 2
N1B N 0.3028(17) -0.0006(12) 0.7945(14) 0.043(3) Uani 0.496(3) 1 d . . P A 2
N2B N 0.3704(4) -0.0151(3) 0.8863(3) 0.0414(10) Uani 0.496(3) 1 d . . P A 2
N3B N 0.4212(17) -0.0849(11) 0.8922(15) 0.088(5) Uani 0.496(3) 1 d . . P A 2
N4B N 0.3648(4) -0.1210(3) 0.7894(5) 0.0442(11) Uani 0.496(3) 1 d . . P A 2
N5B N -0.0206(4) 0.1506(3) 0.5335(3) 0.0338(9) Uani 0.496(3) 1 d . . P A 2
C1B C 0.2314(4) 0.0695(3) 0.7570(4) 0.0291(9) Uani 0.496(3) 1 d . . P A 2
C2B C 0.1323(4) 0.0724(2) 0.6632(3) 0.0282(9) Uani 0.496(3) 1 d . . P A 2
H2B H 0.1025 0.0267 0.6235 0.034 Uiso 0.496(3) 1 calc R U P A 2
C3B C 0.0785(13) 0.1442(8) 0.6296(12) 0.040(4) Uani 0.496(3) 1 d . . P A 2
C4B C 0.1155(4) 0.2112(2) 0.6945(3) 0.0331(10) Uani 0.496(3) 1 d . . P A 2
H4B H 0.0751 0.2594 0.6738 0.040 Uiso 0.496(3) 1 calc R U P A 2
C5B C 0.2119(5) 0.2045(3) 0.7886(4) 0.0361(11) Uani 0.496(3) 1 d . . P A 2
H5B H 0.2376 0.2489 0.8325 0.043 Uiso 0.496(3) 1 calc R U P A 2
C6B C 0.2712(6) 0.1349(4) 0.8196(5) 0.0354(13) Uani 0.496(3) 1 d . . P A 2
H6B H 0.3386 0.1316 0.8832 0.043 Uiso 0.496(3) 1 calc R U P A 2
C7B C 0.2908(5) -0.0674(4) 0.7285(4) 0.0355(11) Uani 0.496(3) 1 d . . P A 2
H7B H 0.2409 -0.0729 0.6564 0.043 Uiso 0.496(3) 1 calc R U P A 2


_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 N5 1.224(2) . ?
O2 N5 1.233(2) . ?
N1 C7 1.341(2) . ?
N1 N2 1.358(2) . ?
N1 C1 1.432(2) . ?
N2 N3 1.280(2) . ?
N3 N4 1.365(2) . ?
N4 C7 1.311(2) . ?
N5 C3 1.476(2) . ?
C1 C2 1.383(2) . ?
C1 C6 1.389(2) . ?
C2 C3 1.377(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.379(2) . ?
C4 C5 1.387(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.397(3) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
O1' N5' 1.224(2) . ?
O2' N5' 1.219(2) . ?
C1' C2' 1.388(2) . ?
C1' C6' 1.393(2) . ?
C1' N1' 1.426(2) . ?
C2' C3' 1.384(2) . ?
C2' H2' 0.9500 . ?
C3' C4' 1.388(2) . ?
C3' N5' 1.473(2) . ?
C4' C5' 1.389(3) . ?
C4' H4' 0.9500 . ?
C5' C6' 1.381(3) . ?
C5' H5' 0.9500 . ?
C6' H6' 0.9500 . ?
C7' N4' 1.308(2) . ?
C7' N1' 1.348(2) . ?
C7' H7' 0.9500 . ?
N1' N2' 1.363(2) . ?
N2' N3' 1.294(2) . ?
N3' N4' 1.369(2) . ?
O1A N5A 1.162(10) . ?
O2A N5A 1.200(6) . ?
N1A C7A 1.350(12) . ?
N1A C1A 1.381(13) . ?
N1A N2A 1.424(10) . ?
N2A N4A 1.291(8) . ?
N3A C7A 1.29(2) . ?
N3A N4A 1.37(2) . ?
N5A C3A 1.50(3) . ?
C1A C2A 1.371(7) . ?
C1A C6A 1.391(8) . ?
C2A C3A 1.22(2) . ?
C2A H2A 0.9500 . ?
C3A C4A 1.537(15) . ?
C4A C5A 1.377(7) . ?
C4A H4A 0.9500 . ?
C5A C6A 1.387(8) . ?
C5A H5A 0.9500 . ?
C6A H6A 0.9500 . ?
C7A H7A 0.9500 . ?
O1B N5B 1.236(6) . ?
O2B N5B 1.25(2) . ?
N1B N2B 1.244(18) . ?
N1B C7B 1.420(18) . ?
N1B C1B 1.46(2) . ?
N2B N3B 1.326(18) . ?
N3B N4B 1.447(19) . ?
N4B C7B 1.341(7) . ?
N5B C3B 1.420(14) . ?
C1B C6B 1.390(9) . ?
C1B C2B 1.396(6) . ?
C2B C3B 1.395(14) . ?
C2B H2B 0.9500 . ?
C3B C4B 1.422(15) . ?
C4B C5B 1.387(7) . ?
C4B H4B 0.9500 . ?
C5B C6B 1.377(8) . ?
C5B H5B 0.9500 . ?
C6B H6B 0.9500 . ?
C7B H7B 0.9500 . ?

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 N1 N2 107.42(15) . . ?
C7 N1 C1 131.19(15) . . ?
N2 N1 C1 121.34(14) . . ?
N3 N2 N1 106.36(14) . . ?
N2 N3 N4 111.73(15) . . ?
C7 N4 N3 104.79(16) . . ?
O1 N5 O2 124.02(16) . . ?
O1 N5 C3 118.47(15) . . ?
O2 N5 C3 117.51(15) . . ?
C2 C1 C6 121.75(16) . . ?
C2 C1 N1 117.95(15) . . ?
C6 C1 N1 120.28(16) . . ?
C3 C2 C1 116.97(16) . . ?
C3 C2 H2 121.5 . . ?
C1 C2 H2 121.5 . . ?
C2 C3 C4 123.93(16) . . ?
C2 C3 N5 117.39(15) . . ?
C4 C3 N5 118.67(16) . . ?
C3 C4 C5 117.79(17) . . ?
C3 C4 H4 121.1 . . ?
C5 C4 H4 121.1 . . ?
C4 C5 C6 120.49(17) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 H5 119.8 . . ?
C1 C6 C5 119.06(16) . . ?
C1 C6 H6 120.5 . . ?
C5 C6 H6 120.5 . . ?
N4 C7 N1 109.70(17) . . ?
N4 C7 H7 125.2 . . ?
N1 C7 H7 125.2 . . ?
C2' C1' C6' 121.47(16) . . ?
C2' C1' N1' 119.13(15) . . ?
C6' C1' N1' 119.39(16) . . ?
C3' C2' C1' 117.25(16) . . ?
C3' C2' H2' 121.4 . . ?
C1' C2' H2' 121.4 . . ?
C2' C3' C4' 123.17(17) . . ?
C2' C3' N5' 118.12(15) . . ?
C4' C3' N5' 118.72(16) . . ?
C3' C4' C5' 117.73(17) . . ?
C3' C4' H4' 121.1 . . ?
C5' C4' H4' 121.1 . . ?
C6' C5' C4' 121.13(17) . . ?
C6' C5' H5' 119.4 . . ?
C4' C5' H5' 119.4 . . ?
C5' C6' C1' 119.24(17) . . ?
C5' C6' H6' 120.4 . . ?
C1' C6' H6' 120.4 . . ?
N4' C7' N1' 109.26(16) . . ?
N4' C7' H7' 125.4 . . ?
N1' C7' H7' 125.4 . . ?
C7' N1' N2' 107.53(15) . . ?
C7' N1' C1' 131.16(15) . . ?
N2' N1' C1' 121.31(15) . . ?
N3' N2' N1' 106.55(15) . . ?
N2' N3' N4' 110.65(15) . . ?
C7' N4' N3' 106.01(16) . . ?
O2' N5' O1' 123.91(16) . . ?
O2' N5' C3' 118.41(16) . . ?
O1' N5' C3' 117.67(15) . . ?
C7A N1A C1A 135.2(7) . . ?
C7A N1A N2A 104.6(8) . . ?
C1A N1A N2A 119.5(8) . . ?
N4A N2A N1A 106.2(6) . . ?
C7A N3A N4A 105.7(16) . . ?
N2A N4A N3A 111.4(11) . . ?
O1A N5A O2A 125.6(7) . . ?
O1A N5A C3A 123.3(8) . . ?
O2A N5A C3A 110.9(8) . . ?
C2A C1A N1A 120.6(6) . . ?
C2A C1A C6A 121.4(6) . . ?
N1A C1A C6A 118.0(6) . . ?
C3A C2A C1A 121.1(10) . . ?
C3A C2A H2A 119.5 . . ?
C1A C2A H2A 119.5 . . ?
C2A C3A N5A 129.2(12) . . ?
C2A C3A C4A 123.1(18) . . ?
N5A C3A C4A 107.3(14) . . ?
C5A C4A C3A 114.3(10) . . ?
C5A C4A H4A 122.9 . . ?
C3A C4A H4A 122.9 . . ?
C4A C5A C6A 120.9(5) . . ?
C4A C5A H5A 119.5 . . ?
C6A C5A H5A 119.5 . . ?
C5A C6A C1A 119.2(6) . . ?
C5A C6A H6A 120.4 . . ?
C1A C6A H6A 120.4 . . ?
N3A C7A N1A 111.9(11) . . ?
N3A C7A H7A 124.1 . . ?
N1A C7A H7A 124.1 . . ?
N2B N1B C7B 110.1(15) . . ?
N2B N1B C1B 127.9(14) . . ?
C7B N1B C1B 121.6(13) . . ?
N1B N2B N3B 111.8(13) . . ?
N2B N3B N4B 105.7(12) . . ?
C7B N4B N3B 106.3(10) . . ?
O1B N5B O2B 122.3(11) . . ?
O1B N5B C3B 117.5(7) . . ?
O2B N5B C3B 120.2(12) . . ?
C6B C1B C2B 121.7(5) . . ?
C6B C1B N1B 115.2(8) . . ?
C2B C1B N1B 123.0(8) . . ?
C3B C2B C1B 118.0(7) . . ?
C3B C2B H2B 121.0 . . ?
C1B C2B H2B 121.0 . . ?
C2B C3B N5B 120.3(11) . . ?
C2B C3B C4B 120.7(10) . . ?
N5B C3B C4B 118.8(9) . . ?
C5B C4B C3B 118.6(6) . . ?
C5B C4B H4B 120.7 . . ?
C3B C4B H4B 120.7 . . ?
C6B C5B C4B 121.3(5) . . ?
C6B C5B H5B 119.3 . . ?
C4B C5B H5B 119.3 . . ?
C5B C6B C1B 119.4(5) . . ?
C5B C6B H6B 120.3 . . ?
C1B C6B H6B 120.3 . . ?
N4B C7B N1B 105.5(10) . . ?
N4B C7B H7B 127.2 . . ?
N1B C7B H7B 127.2 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C7 N1 N2 N3 0.4(2) . . . . ?
C1 N1 N2 N3 -177.30(15) . . . . ?
N1 N2 N3 N4 -0.5(2) . . . . ?
N2 N3 N4 C7 0.4(2) . . . . ?
C7 N1 C1 C2 177.24(19) . . . . ?
N2 N1 C1 C2 -5.6(2) . . . . ?
C7 N1 C1 C6 -4.5(3) . . . . ?
N2 N1 C1 C6 172.63(16) . . . . ?
C6 C1 C2 C3 1.3(3) . . . . ?
N1 C1 C2 C3 179.51(15) . . . . ?
C1 C2 C3 C4 -0.5(3) . . . . ?
C1 C2 C3 N5 -179.39(15) . . . . ?
O1 N5 C3 C2 -174.95(17) . . . . ?
O2 N5 C3 C2 5.3(2) . . . . ?
O1 N5 C3 C4 6.1(3) . . . . ?
O2 N5 C3 C4 -173.64(17) . . . . ?
C2 C3 C4 C5 -0.3(3) . . . . ?
N5 C3 C4 C5 178.57(17) . . . . ?
C3 C4 C5 C6 0.4(3) . . . . ?
C2 C1 C6 C5 -1.3(3) . . . . ?
N1 C1 C6 C5 -179.44(16) . . . . ?
C4 C5 C6 C1 0.4(3) . . . . ?
N3 N4 C7 N1 -0.1(2) . . . . ?
N2 N1 C7 N4 -0.2(2) . . . . ?
C1 N1 C7 N4 177.25(17) . . . . ?
C6' C1' C2' C3' 1.1(3) . . . . ?
N1' C1' C2' C3' -179.49(15) . . . . ?
C1' C2' C3' C4' -0.2(3) . . . . ?
C1' C2' C3' N5' 179.67(16) . . . . ?
C2' C3' C4' C5' -0.9(3) . . . . ?
N5' C3' C4' C5' 179.25(16) . . . . ?
C3' C4' C5' C6' 1.1(3) . . . . ?
C4' C5' C6' C1' -0.3(3) . . . . ?
C2' C1' C6' C5' -0.9(3) . . . . ?
N1' C1' C6' C5' 179.71(16) . . . . ?
N4' C7' N1' N2' 0.4(2) . . . . ?
N4' C7' N1' C1' -179.76(17) . . . . ?
C2' C1' N1' C7' 13.5(3) . . . . ?
C6' C1' N1' C7' -167.02(19) . . . . ?
C2' C1' N1' N2' -166.58(16) . . . . ?
C6' C1' N1' N2' 12.9(2) . . . . ?
C7' N1' N2' N3' -0.5(2) . . . . ?
C1' N1' N2' N3' 179.61(16) . . . . ?
N1' N2' N3' N4' 0.5(2) . . . . ?
N1' C7' N4' N3' -0.1(2) . . . . ?
N2' N3' N4' C7' -0.2(2) . . . . ?
C2' C3' N5' O2' -176.27(18) . . . . ?
C4' C3' N5' O2' 3.6(3) . . . . ?
C2' C3' N5' O1' 4.6(3) . . . . ?
C4' C3' N5' O1' -175.55(17) . . . . ?
C7A N1A N2A N4A -4.0(9) . . . . ?
C1A N1A N2A N4A -175.4(8) . . . . ?
N1A N2A N4A N3A 1.7(11) . . . . ?
C7A N3A N4A N2A 1.4(15) . . . . ?
C7A N1A C1A C2A -159.4(11) . . . . ?
N2A N1A C1A C2A 8.8(13) . . . . ?
C7A N1A C1A C6A 21.9(17) . . . . ?
N2A N1A C1A C6A -170.0(7) . . . . ?
N1A C1A C2A C3A -175.7(14) . . . . ?
C6A C1A C2A C3A 3.1(13) . . . . ?
C1A C2A C3A N5A -176.2(13) . . . . ?
C1A C2A C3A C4A -4(2) . . . . ?
O1A N5A C3A C2A -172.5(16) . . . . ?
O2A N5A C3A C2A 3(2) . . . . ?
O1A N5A C3A C4A 14.8(17) . . . . ?
O2A N5A C3A C4A -169.8(8) . . . . ?
C2A C3A C4A C5A 3(2) . . . . ?
N5A C3A C4A C5A 176.6(8) . . . . ?
C3A C4A C5A C6A -0.7(11) . . . . ?
C4A C5A C6A C1A -0.5(7) . . . . ?
C2A C1A C6A C5A -0.5(7) . . . . ?
N1A C1A C6A C5A 178.3(7) . . . . ?
N4A N3A C7A N1A -4.2(16) . . . . ?
C1A N1A C7A N3A 174.5(15) . . . . ?
N2A N1A C7A N3A 5.1(14) . . . . ?
C7B N1B N2B N3B 6.5(17) . . . . ?
C1B N1B N2B N3B 179.8(15) . . . . ?
N1B N2B N3B N4B -6.5(16) . . . . ?
N2B N3B N4B C7B 3.8(13) . . . . ?
N2B N1B C1B C6B 21(2) . . . . ?
C7B N1B C1B C6B -166.7(11) . . . . ?
N2B N1B C1B C2B -161.2(13) . . . . ?
C7B N1B C1B C2B 11.4(19) . . . . ?
C6B C1B C2B C3B 4.1(9) . . . . ?
N1B C1B C2B C3B -174.0(12) . . . . ?
C1B C2B C3B N5B 178.5(8) . . . . ?
C1B C2B C3B C4B -6.0(15) . . . . ?
O1B N5B C3B C2B 4.4(15) . . . . ?
O2B N5B C3B C2B -171.8(13) . . . . ?
O1B N5B C3B C4B -171.2(8) . . . . ?
O2B N5B C3B C4B 12.6(18) . . . . ?
C2B C3B C4B C5B 4.1(15) . . . . ?
N5B C3B C4B C5B 179.7(8) . . . . ?
C3B C4B C5B C6B -0.1(10) . . . . ?
C4B C5B C6B C1B -1.8(9) . . . . ?
C2B C1B C6B C5B -0.2(8) . . . . ?
N1B C1B C6B C5B 178.0(9) . . . . ?
N3B N4B C7B N1B -0.3(12) . . . . ?
N2B N1B C7B N4B -3.7(15) . . . . ?
C1B N1B C7B N4B -177.5(12) . . . . ?

_refine_diff_density_max         0.302
_refine_diff_density_min         -0.241
_refine_diff_density_rms         0.046

_shelxl_version_number           2014/6

####################################################################### 
# 
# 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_sh372
_database_code_depnum_ccdc_archive 'CCDC 1854063'
_audit_update_record             
;
2018-07-05 deposited with the CCDC.
2018-09-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C7 H5 N5 O2'
_chemical_formula_sum            'C7 H5 N5 O2'
_chemical_formula_weight         191.16

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

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

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

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

_cell_length_a                   7.2094(8)
_cell_length_b                   7.7337(9)
_cell_length_c                   14.2011(16)
_cell_angle_alpha                90
_cell_angle_beta                 93.215(2)
_cell_angle_gamma                90
_cell_volume                     790.54(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    8310
_cell_measurement_theta_min      2.83
_cell_measurement_theta_max      30.14

_exptl_crystal_description       prizm
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.606
_exptl_crystal_F_000             392
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_exptl_absorpt_coefficient_mu    0.125
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            22139
_diffrn_reflns_av_unetI/netI     0.0142
_diffrn_reflns_av_R_equivalents  0.0309
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.830
_diffrn_reflns_theta_max         30.201
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2339
_reflns_number_gt                2022
_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       'APEX (Bruker, 2009)'
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_reduction        'SAINT (Bruker, 2009)'
_computing_structure_solution    'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_publication_material  
'SHELXL-2014/6 (Sheldrick, 2014) and PLATON (Spek, 2009)'
_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)+(0.0637P)²+0.2388P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2339
_refine_ls_number_parameters     127
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0455
_refine_ls_R_factor_gt           0.0382
_refine_ls_wR_factor_ref         0.1132
_refine_ls_wR_factor_gt          0.1046
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_restrained_S_all      1.049
_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 0.36342(13) 0.51331(11) 0.36677(7) 0.0332(2) Uani 1 1 d . . . . .
O2 O 0.43183(13) 0.31334(12) 0.26804(6) 0.0313(2) Uani 1 1 d . . . . .
N1 N 0.17579(11) -0.14799(10) 0.60261(6) 0.01601(18) Uani 1 1 d . . . . .
N2 N 0.20238(13) -0.31881(11) 0.58522(7) 0.0229(2) Uani 1 1 d . . . . .
N3 N 0.13986(13) -0.40249(12) 0.65576(7) 0.0241(2) Uani 1 1 d . . . . .
N4 N 0.07192(12) -0.29030(12) 0.72042(6) 0.0219(2) Uani 1 1 d . . . . .
N5 N 0.37760(12) 0.36116(12) 0.34428(6) 0.02124(19) Uani 1 1 d . . . . .
C1 C 0.09636(14) -0.13435(13) 0.68621(7) 0.0191(2) Uani 1 1 d . . . . .
H1 H 0.0635 -0.0292 0.7156 0.023 Uiso 1 1 calc R U . . .
C2 C 0.22637(12) -0.01883(12) 0.53694(6) 0.01530(19) Uani 1 1 d . . . . .
C3 C 0.21642(13) 0.15531(12) 0.56262(7) 0.01735(19) Uani 1 1 d . . . . .
H3 H 0.1758 0.1875 0.6226 0.021 Uiso 1 1 calc R U . . .
C4 C 0.26721(14) 0.28050(12) 0.49862(7) 0.0186(2) Uani 1 1 d . . . . .
H4 H 0.2617 0.3998 0.5141 0.022 Uiso 1 1 calc R U . . .
C5 C 0.32605(13) 0.22771(12) 0.41169(6) 0.01608(19) Uani 1 1 d . . . . .
C6 C 0.33529(13) 0.05511(13) 0.38536(7) 0.01748(19) Uani 1 1 d . . . . .
H6 H 0.3760 0.0235 0.3253 0.021 Uiso 1 1 calc R U . . .
C7 C 0.28350(13) -0.07046(12) 0.44903(6) 0.01649(19) Uani 1 1 d . . . . .
H7 H 0.2870 -0.1896 0.4328 0.020 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 N5 1.2250(13) . ?
O2 N5 1.2286(12) . ?
N1 C1 1.3509(12) . ?
N1 N2 1.3595(11) . ?
N1 C2 1.4278(12) . ?
N2 N3 1.2946(12) . ?
N3 N4 1.3734(13) . ?
N4 C1 1.3158(13) . ?
N5 C5 1.4696(12) . ?
C1 H1 0.9500 . ?
C2 C7 1.3947(13) . ?
C2 C3 1.3982(13) . ?
C3 C4 1.3910(13) . ?
C3 H3 0.9500 . ?
C4 C5 1.3890(13) . ?
C4 H4 0.9500 . ?
C5 C6 1.3888(13) . ?
C6 C7 1.3921(13) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 N2 107.85(8) . . ?
C1 N1 C2 130.98(8) . . ?
N2 N1 C2 121.16(8) . . ?
N3 N2 N1 106.65(8) . . ?
N2 N3 N4 110.75(9) . . ?
C1 N4 N3 105.79(8) . . ?
O1 N5 O2 123.66(9) . . ?
O1 N5 C5 118.48(9) . . ?
O2 N5 C5 117.86(9) . . ?
N4 C1 N1 108.97(9) . . ?
N4 C1 H1 125.5 . . ?
N1 C1 H1 125.5 . . ?
C7 C2 C3 122.09(9) . . ?
C7 C2 N1 118.91(8) . . ?
C3 C2 N1 118.99(8) . . ?
C4 C3 C2 118.74(9) . . ?
C4 C3 H3 120.6 . . ?
C2 C3 H3 120.6 . . ?
C5 C4 C3 118.74(9) . . ?
C5 C4 H4 120.6 . . ?
C3 C4 H4 120.6 . . ?
C4 C5 C6 122.92(9) . . ?
C4 C5 N5 118.27(8) . . ?
C6 C5 N5 118.80(8) . . ?
C5 C6 C7 118.48(9) . . ?
C5 C6 H6 120.8 . . ?
C7 C6 H6 120.8 . . ?
C6 C7 C2 119.02(9) . . ?
C6 C7 H7 120.5 . . ?
C2 C7 H7 120.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 N1 N2 N3 0.35(11) . . . . ?
C2 N1 N2 N3 -178.63(8) . . . . ?
N1 N2 N3 N4 -0.11(11) . . . . ?
N2 N3 N4 C1 -0.18(12) . . . . ?
N3 N4 C1 N1 0.40(11) . . . . ?
N2 N1 C1 N4 -0.48(11) . . . . ?
C2 N1 C1 N4 178.37(9) . . . . ?
C1 N1 C2 C7 -171.16(10) . . . . ?
N2 N1 C2 C7 7.55(13) . . . . ?
C1 N1 C2 C3 8.60(15) . . . . ?
N2 N1 C2 C3 -172.68(9) . . . . ?
C7 C2 C3 C4 -0.72(14) . . . . ?
N1 C2 C3 C4 179.52(8) . . . . ?
C2 C3 C4 C5 -0.07(14) . . . . ?
C3 C4 C5 C6 0.48(15) . . . . ?
C3 C4 C5 N5 179.41(8) . . . . ?
O1 N5 C5 C4 -1.30(14) . . . . ?
O2 N5 C5 C4 179.06(9) . . . . ?
O1 N5 C5 C6 177.67(9) . . . . ?
O2 N5 C5 C6 -1.97(13) . . . . ?
C4 C5 C6 C7 -0.10(15) . . . . ?
N5 C5 C6 C7 -179.02(8) . . . . ?
C5 C6 C7 C2 -0.68(14) . . . . ?
C3 C2 C7 C6 1.10(14) . . . . ?
N1 C2 C7 C6 -179.14(8) . . . . ?

_refine_diff_density_max         0.349
_refine_diff_density_min         -0.283
_refine_diff_density_rms         0.052

_shelxl_version_number           2014/6

####################################################################### 
# 
# 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_sh371
_database_code_depnum_ccdc_archive 'CCDC 1854067'
_audit_update_record             
;
2018-07-05 deposited with the CCDC.
2018-09-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 H3 N5 O4'
_chemical_formula_sum            'C6 H3 N5 O4'
_chemical_formula_weight         209.13

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                   9.7268(6)
_cell_length_b                   8.3199(5)
_cell_length_c                   9.8210(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     794.77(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    3266
_cell_measurement_theta_min      3.21
_cell_measurement_theta_max      29.20

_exptl_crystal_description       prizm
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.748
_exptl_crystal_F_000             424
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.19
_exptl_absorpt_coefficient_mu    0.150
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7840
_diffrn_reflns_av_unetI/netI     0.0239
_diffrn_reflns_av_R_equivalents  0.0263
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.209
_diffrn_reflns_theta_max         29.196
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2149
_reflns_number_gt                1984
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.892
_reflns_Friedel_fraction_max     0.996
_reflns_Friedel_fraction_full    1.000

_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       'APEX (Bruker, 2009)'
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_reduction        'SAINT (Bruker, 2009)'
_computing_structure_solution    'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_publication_material  
'SHELXL-2014/6 (Sheldrick, 2014) and PLATON (Spek, 2009)'
_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)+(0.0307P)²+0.1593P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 887 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.4(5)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2149
_refine_ls_number_parameters     148
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0317
_refine_ls_R_factor_gt           0.0280
_refine_ls_wR_factor_ref         0.0668
_refine_ls_wR_factor_gt          0.0648
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_restrained_S_all      1.042
_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 0.82707(15) 0.09397(17) 0.25880(16) 0.0236(3) Uani 1 1 d . . . . .
O2 O 0.64428(15) 0.06359(16) 0.38305(17) 0.0236(3) Uani 1 1 d . . . . .
O3 O 0.40603(16) 0.5176(2) 0.55856(16) 0.0288(4) Uani 1 1 d . . . . .
O4 O 0.49323(15) 0.75647(17) 0.54304(15) 0.0229(3) Uani 1 1 d . . . . .
N1 N 0.90483(18) 0.6975(2) 0.24861(18) 0.0203(3) Uani 1 1 d . . . . .
N2 N 1.00077(18) 0.64164(19) 0.17880(17) 0.0182(3) Uani 1 1 d . . . . .
N3 N 1.09241(19) 0.6116(2) 0.11353(18) 0.0243(4) Uani 1 1 d . . . . .
N4 N 0.73175(17) 0.14713(19) 0.32647(17) 0.0174(3) Uani 1 1 d . . . . .
N5 N 0.49439(17) 0.6116(2) 0.51887(16) 0.0190(3) Uani 1 1 d . . . . .
C1 C 0.81084(19) 0.5852(2) 0.30479(18) 0.0159(4) Uani 1 1 d . . . . .
C2 C 0.82064(19) 0.4194(2) 0.28483(18) 0.0151(4) Uani 1 1 d . . . . .
C3 C 0.7215(2) 0.3231(2) 0.34353(18) 0.0150(4) Uani 1 1 d . . . . .
C4 C 0.6129(2) 0.3815(2) 0.41888(18) 0.0161(4) Uani 1 1 d . . . . .
C5 C 0.6084(2) 0.5465(2) 0.43709(19) 0.0156(3) Uani 1 1 d . . . . .
C6 C 0.70498(19) 0.6506(2) 0.3833(2) 0.0169(4) Uani 1 1 d . . . . .
H2 H 0.891(2) 0.374(3) 0.234(2) 0.015(6) Uiso 1 1 d . . . . .
H6 H 0.697(2) 0.757(3) 0.397(2) 0.015(5) Uiso 1 1 d . . . . .
H4 H 0.547(3) 0.311(3) 0.458(3) 0.030(7) 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
O1 N4 1.224(2) . ?
O2 N4 1.231(2) . ?
O3 N5 1.226(2) . ?
O4 N5 1.228(2) . ?
N1 N2 1.248(2) . ?
N1 C1 1.419(2) . ?
N2 N3 1.126(2) . ?
N4 C3 1.477(2) . ?
N5 C5 1.472(2) . ?
C1 C6 1.396(3) . ?
C1 C2 1.397(3) . ?
C2 C3 1.380(3) . ?
C2 H2 0.93(2) . ?
C3 C4 1.378(3) . ?
C4 C5 1.385(3) . ?
C4 H4 0.95(3) . ?
C5 C6 1.383(3) . ?
C6 H6 0.90(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
N2 N1 C1 116.75(16) . . ?
N3 N2 N1 170.94(19) . . ?
O1 N4 O2 124.39(16) . . ?
O1 N4 C3 118.11(16) . . ?
O2 N4 C3 117.49(16) . . ?
O3 N5 O4 123.93(17) . . ?
O3 N5 C5 117.81(16) . . ?
O4 N5 C5 118.26(16) . . ?
C6 C1 C2 120.81(17) . . ?
C6 C1 N1 115.69(16) . . ?
C2 C1 N1 123.50(17) . . ?
C3 C2 C1 117.83(17) . . ?
C3 C2 H2 120.1(14) . . ?
C1 C2 H2 122.0(14) . . ?
C4 C3 C2 123.76(16) . . ?
C4 C3 N4 117.52(17) . . ?
C2 C3 N4 118.72(17) . . ?
C3 C4 C5 116.30(17) . . ?
C3 C4 H4 120.9(17) . . ?
C5 C4 H4 122.7(17) . . ?
C6 C5 C4 123.36(18) . . ?
C6 C5 N5 119.30(17) . . ?
C4 C5 N5 117.34(17) . . ?
C5 C6 C1 117.91(17) . . ?
C5 C6 H6 120.2(16) . . ?
C1 C6 H6 121.9(16) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N2 N1 C1 C6 179.56(18) . . . . ?
N2 N1 C1 C2 -0.4(3) . . . . ?
C6 C1 C2 C3 0.9(3) . . . . ?
N1 C1 C2 C3 -179.12(17) . . . . ?
C1 C2 C3 C4 0.9(3) . . . . ?
C1 C2 C3 N4 -178.55(16) . . . . ?
O1 N4 C3 C4 179.39(17) . . . . ?
O2 N4 C3 C4 -1.5(3) . . . . ?
O1 N4 C3 C2 -1.2(3) . . . . ?
O2 N4 C3 C2 177.97(17) . . . . ?
C2 C3 C4 C5 -1.5(3) . . . . ?
N4 C3 C4 C5 177.89(16) . . . . ?
C3 C4 C5 C6 0.5(3) . . . . ?
C3 C4 C5 N5 -179.17(16) . . . . ?
O3 N5 C5 C6 175.85(17) . . . . ?
O4 N5 C5 C6 -4.0(2) . . . . ?
O3 N5 C5 C4 -4.5(3) . . . . ?
O4 N5 C5 C4 175.68(17) . . . . ?
C4 C5 C6 C1 1.1(3) . . . . ?
N5 C5 C6 C1 -179.22(17) . . . . ?
C2 C1 C6 C5 -1.8(3) . . . . ?
N1 C1 C6 C5 178.18(17) . . . . ?

_refine_diff_density_max         0.264
_refine_diff_density_min         -0.173
_refine_diff_density_rms         0.039

_shelxl_version_number           2014/6

