# Electronic Supplementary Material (ESI) for Chemical Communications.
# 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. 
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#######################################################################

data_shrv611
_database_code_depnum_ccdc_archive 'CCDC 1848968'
_audit_update_record             
;
2018-06-12 deposited with the CCDC.
2018-08-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 H6 N8 O4, C2 H3 N'
_chemical_formula_sum            'C8 H9 N9 O4'
_chemical_formula_weight         295.24

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

_space_group_crystal_system      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                   7.7715(4)
_cell_length_b                   29.4724(14)
_cell_length_c                   11.6745(6)
_cell_angle_alpha                90
_cell_angle_beta                 96.9890(10)
_cell_angle_gamma                90
_cell_volume                     2654.1(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    6048
_cell_measurement_theta_min      2.718
_cell_measurement_theta_max      24.513

_exptl_crystal_description       needle
_exptl_crystal_colour            'clear orange'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.478
_exptl_crystal_F_000             1216
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.173
_exptl_crystal_size_mid          0.064
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    0.122
_shelx_estimated_absorpt_T_min   0.979
_shelx_estimated_absorpt_T_max   0.998
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6725
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_process_details   'SADABS v2014/5 (Bruker, 2008)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker SMART APEX II CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            27200
_diffrn_reflns_av_unetI/netI     0.0381
_diffrn_reflns_av_R_equivalents  0.0434
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -38
_diffrn_reflns_limit_k_max       38
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.276
_diffrn_reflns_theta_max         27.482
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.991
_reflns_number_total             6033
_reflns_number_gt                4201
_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       'Bruker APEX3 v2015.5-2 (Bruker, 2015)'
_computing_cell_refinement       'Bruker APEX3 v2015.5-2 (Bruker, 2015)'
_computing_data_reduction        
;
Bruker SAINT v8.34A (Bruker, 2013), Bruker XPREP v2014/2 (Bruker, 2014)
;
_computing_structure_solution    'Bruker SHELXTL v2014/7 (Bruker, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL v2014/7 (Bruker, 2014)'
_computing_publication_material  'Bruker SHELXTL v2014/7 (Bruker, 2014)'
_refine_special_details          
;
One acetonitrile molecule displayed two component disorder with a 
0.74:0.26 ratio between the major and minor components.  Enhanced 
rigid-bond restraints were applied to all atoms (esds = 0.004). 
Bond lenghts for disorded acetonitrile molecules were restrained to
literature values.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0621P)²+1.2287P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6033
_refine_ls_number_parameters     395
_refine_ls_number_restraints     306
_refine_ls_R_factor_all          0.0836
_refine_ls_R_factor_gt           0.0531
_refine_ls_wR_factor_ref         0.1439
_refine_ls_wR_factor_gt          0.1283
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_restrained_S_all      1.022
_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 0.1147(2) 0.63793(5) 0.19765(13) 0.0463(4) Uani 1 1 d . U . . .
O2 O 0.0210(2) 0.69158(5) 0.07932(14) 0.0533(5) Uani 1 1 d . U . . .
N3 N 0.1157(2) 0.67820(5) 0.16708(14) 0.0348(4) Uani 1 1 d . U . . .
C4 C 0.2193(3) 0.70950(6) 0.23004(17) 0.0307(4) Uani 1 1 d . U . . .
C5 C 0.2203(3) 0.75621(7) 0.20727(18) 0.0343(5) Uani 1 1 d . U . . .
N6 N 0.1393(3) 0.78032(6) 0.12116(18) 0.0504(5) Uani 1 1 d . U . . .
H6A H 0.1521 0.8093 0.1199 0.061 Uiso 1 1 calc R U . . .
H6B H 0.0741 0.7670 0.0665 0.061 Uiso 1 1 calc R U . . .
N7 N 0.3248(2) 0.77390(6) 0.29629(17) 0.0420(5) Uani 1 1 d . U . . .
H7 H 0.3464 0.8024 0.3037 0.050 Uiso 1 1 calc R U . . .
N8 N 0.3938(2) 0.74174(6) 0.37453(16) 0.0388(4) Uani 1 1 d . U . . .
C9 C 0.3308(3) 0.70291(6) 0.33446(17) 0.0306(4) Uani 1 1 d . U . . .
C10 C 0.3815(2) 0.66118(6) 0.39815(16) 0.0290(4) Uani 1 1 d . U . . .
N11 N 0.3470(2) 0.65671(5) 0.50480(14) 0.0339(4) Uani 1 1 d . U . . .
N12 N 0.4192(2) 0.61579(6) 0.54159(14) 0.0342(4) Uani 1 1 d . U . . .
H12 H 0.4131 0.6049 0.6094 0.041 Uiso 1 1 calc R U . . .
C13 C 0.4999(3) 0.59448(6) 0.46207(17) 0.0307(4) Uani 1 1 d . U . . .
N14 N 0.5783(3) 0.55467(6) 0.47810(17) 0.0431(5) Uani 1 1 d . U . . .
H14A H 0.5795 0.5408 0.5430 0.052 Uiso 1 1 calc R U . . .
H14B H 0.6280 0.5427 0.4236 0.052 Uiso 1 1 calc R U . . .
C15 C 0.4783(3) 0.62340(6) 0.36556(16) 0.0304(4) Uani 1 1 d . U . . .
N16 N 0.5543(3) 0.61686(6) 0.26570(15) 0.0416(4) Uani 1 1 d . U . . .
O17 O 0.5282(3) 0.64451(6) 0.18570(14) 0.0582(5) Uani 1 1 d . U . . .
O18 O 0.6506(3) 0.58335(6) 0.26080(16) 0.0631(5) Uani 1 1 d . U . . .
O19 O -0.1178(2) 0.48015(6) 0.26299(14) 0.0552(5) Uani 1 1 d . U . . .
O20 O -0.1907(3) 0.48517(6) 0.43591(16) 0.0570(5) Uani 1 1 d . U . . .
N21 N -0.1095(2) 0.46684(6) 0.36341(16) 0.0375(4) Uani 1 1 d . U . . .
C22 C -0.0077(3) 0.42926(6) 0.39850(17) 0.0301(4) Uani 1 1 d . U . . .
C23 C -0.0035(3) 0.40849(6) 0.50742(17) 0.0309(4) Uani 1 1 d . U . . .
N24 N -0.0714(3) 0.42114(6) 0.60154(15) 0.0407(4) Uani 1 1 d . U . . .
H24A H -0.0551 0.4048 0.6630 0.049 Uiso 1 1 calc R U . . .
H24B H -0.1316 0.4456 0.6010 0.049 Uiso 1 1 calc R U . . .
N25 N 0.0920(2) 0.37095(5) 0.49981(15) 0.0360(4) Uani 1 1 d . U . . .
H25 H 0.1138 0.3519 0.5554 0.043 Uiso 1 1 calc R U . . .
N26 N 0.1516(2) 0.36592(5) 0.39451(15) 0.0359(4) Uani 1 1 d . U . . .
C27 C 0.0923(3) 0.40141(6) 0.33323(17) 0.0308(4) Uani 1 1 d . U . . .
C28 C 0.1314(3) 0.40626(6) 0.21423(17) 0.0334(5) Uani 1 1 d . U . . .
N29 N 0.1105(3) 0.37075(6) 0.14516(15) 0.0423(4) Uani 1 1 d . U . . .
N30 N 0.1542(3) 0.38587(7) 0.04072(16) 0.0490(5) Uani 1 1 d . U . . .
H30 H 0.1546 0.3687 -0.0187 0.059 Uiso 1 1 calc R U . . .
C31 C 0.1958(4) 0.42990(8) 0.04084(19) 0.0478(6) Uani 1 1 d . U . . .
N32 N 0.2388(4) 0.45247(9) -0.04933(19) 0.0781(8) Uani 1 1 d . U . . .
H32A H 0.2413 0.4388 -0.1142 0.094 Uiso 1 1 calc R U . . .
H32B H 0.2641 0.4808 -0.0432 0.094 Uiso 1 1 calc R U . . .
C33 C 0.1856(3) 0.44428(7) 0.15459(18) 0.0400(5) Uani 1 1 d . U . . .
N34 N 0.2384(3) 0.48679(6) 0.19792(17) 0.0534(6) Uani 1 1 d . U . . .
O35 O 0.2655(5) 0.51672(7) 0.12909(19) 0.1079(11) Uani 1 1 d . U . . .
O36 O 0.2573(2) 0.49315(5) 0.30345(13) 0.0510(4) Uani 1 1 d . U . . .
N37 N 0.1679(4) 0.29534(10) 0.6638(3) 0.0899(9) Uani 1 1 d . U . . .
C38 C 0.2269(5) 0.27281(13) 0.7351(4) 0.0990(14) Uani 1 1 d . U . . .
C39 C 0.3111(6) 0.2473(2) 0.8368(5) 0.157(3) Uani 1 1 d . U . . .
H39A H 0.4318 0.2551 0.8500 0.235 Uiso 1 1 calc R U . . .
H39B H 0.2995 0.2153 0.8223 0.235 Uiso 1 1 calc R U . . .
H39C H 0.2564 0.2550 0.9036 0.235 Uiso 1 1 calc R U . . .
N40A N 0.4290(12) 0.6016(4) 0.7760(5) 0.149(4) Uani 0.743(7) 1 d D U P A 1
C41A C 0.3688(6) 0.6043(3) 0.8630(3) 0.0760(16) Uani 0.743(7) 1 d D U P A 1
C42A C 0.3009(7) 0.5959(2) 0.9686(3) 0.102(2) Uani 0.743(7) 1 d D U P A 1
H42A H 0.1984 0.5776 0.9542 0.153 Uiso 0.743(7) 1 calc R U P A 1
H42B H 0.2725 0.6243 1.0024 0.153 Uiso 0.743(7) 1 calc R U P A 1
H42C H 0.3859 0.5803 1.0207 0.153 Uiso 0.743(7) 1 calc R U P A 1
N40B N 0.393(3) 0.5954(5) 0.7847(18) 0.068(4) Uiso 0.257(7) 1 d D . P A 2
C41B C 0.387(4) 0.6278(9) 0.836(3) 0.150(12) Uiso 0.257(7) 1 d D . P A 2
C42B C 0.372(3) 0.6702(6) 0.8969(18) 0.144(9) Uiso 0.257(7) 1 d D . P A 2
H42D H 0.4858 0.6803 0.9284 0.216 Uiso 0.257(7) 1 calc R U P A 2
H42E H 0.3023 0.6658 0.9582 0.216 Uiso 0.257(7) 1 calc R U P A 2
H42F H 0.3196 0.6927 0.8443 0.216 Uiso 0.257(7) 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 N3 1.240(2) . ?
O2 N3 1.250(2) . ?
N3 C4 1.376(2) . ?
C4 C5 1.402(3) . ?
C4 C9 1.420(3) . ?
C5 N6 1.326(3) . ?
C5 N7 1.344(3) . ?
N6 H6A 0.8600 . ?
N6 H6B 0.8600 . ?
N7 N8 1.379(2) . ?
N7 H7 0.8600 . ?
N8 C9 1.309(2) . ?
C9 C10 1.466(3) . ?
C10 N11 1.312(3) . ?
C10 C15 1.421(3) . ?
N11 N12 1.377(2) . ?
N12 C13 1.338(3) . ?
N12 H12 0.8600 . ?
C13 N14 1.325(2) . ?
C13 C15 1.406(3) . ?
N14 H14A 0.8600 . ?
N14 H14B 0.8600 . ?
C15 N16 1.383(3) . ?
N16 O17 1.238(2) . ?
N16 O18 1.245(2) . ?
O19 N21 1.230(2) . ?
O20 N21 1.240(2) . ?
N21 C22 1.393(2) . ?
C22 C23 1.408(3) . ?
C22 C27 1.415(3) . ?
C23 N24 1.329(3) . ?
C23 N25 1.341(3) . ?
N24 H24A 0.8600 . ?
N24 H24B 0.8600 . ?
N25 N26 1.373(2) . ?
N25 H25 0.8600 . ?
N26 C27 1.318(2) . ?
C27 C28 1.465(3) . ?
C28 N29 1.319(2) . ?
C28 C33 1.410(3) . ?
N29 N30 1.379(3) . ?
N30 C31 1.337(3) . ?
N30 H30 0.8600 . ?
C31 N32 1.322(3) . ?
C31 C33 1.405(3) . ?
N32 H32A 0.8600 . ?
N32 H32B 0.8600 . ?
C33 N34 1.394(3) . ?
N34 O35 1.228(3) . ?
N34 O36 1.237(2) . ?
N37 C38 1.119(4) . ?
C38 C39 1.488(5) . ?
C39 H39A 0.9600 . ?
C39 H39B 0.9600 . ?
C39 H39C 0.9600 . ?
N40A C41A 1.171(5) . ?
C41A C42A 1.421(5) . ?
C42A H42A 0.9600 . ?
C42A H42B 0.9600 . ?
C42A H42C 0.9600 . ?
N40B C41B 1.131(7) . ?
C41B C42B 1.449(7) . ?
C42B H42D 0.9600 . ?
C42B H42E 0.9600 . ?
C42B H42F 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 N3 O2 120.94(16) . . ?
O1 N3 C4 120.76(16) . . ?
O2 N3 C4 118.29(16) . . ?
N3 C4 C5 124.96(17) . . ?
N3 C4 C9 128.53(17) . . ?
C5 C4 C9 106.24(16) . . ?
N6 C5 N7 124.39(19) . . ?
N6 C5 C4 131.05(19) . . ?
N7 C5 C4 104.55(17) . . ?
C5 N6 H6A 120.0 . . ?
C5 N6 H6B 120.0 . . ?
H6A N6 H6B 120.0 . . ?
C5 N7 N8 113.29(16) . . ?
C5 N7 H7 123.4 . . ?
N8 N7 H7 123.4 . . ?
C9 N8 N7 105.40(16) . . ?
N8 C9 C4 110.50(16) . . ?
N8 C9 C10 119.09(17) . . ?
C4 C9 C10 130.40(17) . . ?
N11 C10 C15 110.57(16) . . ?
N11 C10 C9 119.48(17) . . ?
C15 C10 C9 129.79(18) . . ?
C10 N11 N12 105.15(16) . . ?
C13 N12 N11 113.73(16) . . ?
C13 N12 H12 123.1 . . ?
N11 N12 H12 123.1 . . ?
N14 C13 N12 124.32(19) . . ?
N14 C13 C15 131.1(2) . . ?
N12 C13 C15 104.54(17) . . ?
C13 N14 H14A 120.0 . . ?
C13 N14 H14B 120.0 . . ?
H14A N14 H14B 120.0 . . ?
N16 C15 C13 124.70(18) . . ?
N16 C15 C10 128.98(18) . . ?
C13 C15 C10 106.01(17) . . ?
O17 N16 O18 122.2(2) . . ?
O17 N16 C15 119.77(18) . . ?
O18 N16 C15 118.05(18) . . ?
O19 N21 O20 122.65(18) . . ?
O19 N21 C22 119.71(18) . . ?
O20 N21 C22 117.64(17) . . ?
N21 C22 C23 124.11(19) . . ?
N21 C22 C27 129.20(18) . . ?
C23 C22 C27 106.29(16) . . ?
N24 C23 N25 124.39(19) . . ?
N24 C23 C22 131.08(19) . . ?
N25 C23 C22 104.52(18) . . ?
C23 N24 H24A 120.0 . . ?
C23 N24 H24B 120.0 . . ?
H24A N24 H24B 120.0 . . ?
C23 N25 N26 113.46(16) . . ?
C23 N25 H25 123.3 . . ?
N26 N25 H25 123.3 . . ?
C27 N26 N25 105.44(16) . . ?
N26 C27 C22 110.28(18) . . ?
N26 C27 C28 119.53(17) . . ?
C22 C27 C28 130.17(17) . . ?
N29 C28 C33 110.51(19) . . ?
N29 C28 C27 118.56(18) . . ?
C33 C28 C27 130.90(17) . . ?
C28 N29 N30 105.01(18) . . ?
C31 N30 N29 113.47(17) . . ?
C31 N30 H30 123.3 . . ?
N29 N30 H30 123.3 . . ?
N32 C31 N30 124.9(2) . . ?
N32 C31 C33 130.5(2) . . ?
N30 C31 C33 104.6(2) . . ?
C31 N32 H32A 120.0 . . ?
C31 N32 H32B 120.0 . . ?
H32A N32 H32B 120.0 . . ?
N34 C33 C31 124.5(2) . . ?
N34 C33 C28 128.84(19) . . ?
C31 C33 C28 106.36(19) . . ?
O35 N34 O36 122.2(2) . . ?
O35 N34 C33 118.3(2) . . ?
O36 N34 C33 119.44(18) . . ?
N37 C38 C39 174.0(5) . . ?
C38 C39 H39A 109.5 . . ?
C38 C39 H39B 109.5 . . ?
H39A C39 H39B 109.5 . . ?
C38 C39 H39C 109.5 . . ?
H39A C39 H39C 109.5 . . ?
H39B C39 H39C 109.5 . . ?
N40A C41A C42A 166.0(10) . . ?
C41A C42A H42A 109.5 . . ?
C41A C42A H42B 109.5 . . ?
H42A C42A H42B 109.5 . . ?
C41A C42A H42C 109.5 . . ?
H42A C42A H42C 109.5 . . ?
H42B C42A H42C 109.5 . . ?
N40B C41B C42B 177(3) . . ?
C41B C42B H42D 109.5 . . ?
C41B C42B H42E 109.5 . . ?
H42D C42B H42E 109.5 . . ?
C41B C42B H42F 109.5 . . ?
H42D C42B H42F 109.5 . . ?
H42E C42B H42F 109.5 . . ?

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
O1 N3 C4 C5 -175.2(2) . . . . ?
O2 N3 C4 C5 3.8(3) . . . . ?
O1 N3 C4 C9 -2.0(3) . . . . ?
O2 N3 C4 C9 177.0(2) . . . . ?
N3 C4 C5 N6 -5.7(4) . . . . ?
C9 C4 C5 N6 179.8(2) . . . . ?
N3 C4 C5 N7 173.4(2) . . . . ?
C9 C4 C5 N7 -1.1(2) . . . . ?
N6 C5 N7 N8 -179.8(2) . . . . ?
C4 C5 N7 N8 0.9(3) . . . . ?
C5 N7 N8 C9 -0.4(3) . . . . ?
N7 N8 C9 C4 -0.3(2) . . . . ?
N7 N8 C9 C10 179.32(18) . . . . ?
N3 C4 C9 N8 -173.3(2) . . . . ?
C5 C4 C9 N8 0.9(3) . . . . ?
N3 C4 C9 C10 7.1(4) . . . . ?
C5 C4 C9 C10 -178.7(2) . . . . ?
N8 C9 C10 N11 60.1(3) . . . . ?
C4 C9 C10 N11 -120.4(2) . . . . ?
N8 C9 C10 C15 -114.8(2) . . . . ?
C4 C9 C10 C15 64.7(3) . . . . ?
C15 C10 N11 N12 -0.7(2) . . . . ?
C9 C10 N11 N12 -176.52(16) . . . . ?
C10 N11 N12 C13 0.7(2) . . . . ?
N11 N12 C13 N14 -179.82(18) . . . . ?
N11 N12 C13 C15 -0.3(2) . . . . ?
N14 C13 C15 N16 -6.6(3) . . . . ?
N12 C13 C15 N16 173.97(19) . . . . ?
N14 C13 C15 C10 179.3(2) . . . . ?
N12 C13 C15 C10 -0.1(2) . . . . ?
N11 C10 C15 N16 -173.21(19) . . . . ?
C9 C10 C15 N16 2.0(3) . . . . ?
N11 C10 C15 C13 0.5(2) . . . . ?
C9 C10 C15 C13 175.79(18) . . . . ?
C13 C15 N16 O17 -179.5(2) . . . . ?
C10 C15 N16 O17 -6.8(3) . . . . ?
C13 C15 N16 O18 -0.9(3) . . . . ?
C10 C15 N16 O18 171.7(2) . . . . ?
O19 N21 C22 C23 -173.1(2) . . . . ?
O20 N21 C22 C23 5.9(3) . . . . ?
O19 N21 C22 C27 -1.3(3) . . . . ?
O20 N21 C22 C27 177.7(2) . . . . ?
N21 C22 C23 N24 -8.9(3) . . . . ?
C27 C22 C23 N24 177.8(2) . . . . ?
N21 C22 C23 N25 172.46(18) . . . . ?
C27 C22 C23 N25 -0.9(2) . . . . ?
N24 C23 N25 N26 -178.26(18) . . . . ?
C22 C23 N25 N26 0.5(2) . . . . ?
C23 N25 N26 C27 0.1(2) . . . . ?
N25 N26 C27 C22 -0.7(2) . . . . ?
N25 N26 C27 C28 -179.32(17) . . . . ?
N21 C22 C27 N26 -171.9(2) . . . . ?
C23 C22 C27 N26 1.0(2) . . . . ?
N21 C22 C27 C28 6.6(4) . . . . ?
C23 C22 C27 C28 179.5(2) . . . . ?
N26 C27 C28 N29 46.7(3) . . . . ?
C22 C27 C28 N29 -131.7(2) . . . . ?
N26 C27 C28 C33 -135.6(2) . . . . ?
C22 C27 C28 C33 46.1(4) . . . . ?
C33 C28 N29 N30 0.9(2) . . . . ?
C27 C28 N29 N30 179.07(18) . . . . ?
C28 N29 N30 C31 -2.2(3) . . . . ?
N29 N30 C31 N32 -178.6(3) . . . . ?
N29 N30 C31 C33 2.5(3) . . . . ?
N32 C31 C33 N34 -6.8(5) . . . . ?
N30 C31 C33 N34 172.1(2) . . . . ?
N32 C31 C33 C28 179.3(3) . . . . ?
N30 C31 C33 C28 -1.8(3) . . . . ?
N29 C28 C33 N34 -173.0(2) . . . . ?
C27 C28 C33 N34 9.1(4) . . . . ?
N29 C28 C33 C31 0.6(3) . . . . ?
C27 C28 C33 C31 -177.3(2) . . . . ?
C31 C33 N34 O35 14.2(4) . . . . ?
C28 C33 N34 O35 -173.4(3) . . . . ?
C31 C33 N34 O36 -165.5(2) . . . . ?
C28 C33 N34 O36 7.0(4) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N6 H6A N26 0.86 2.28 3.018(2) 143.8 2
N6 H6B O2 0.86 2.27 2.796(2) 119.6 .
N6 H6B N8 0.86 2.51 3.319(3) 157.6 4_575
N7 H7 N29 0.86 2.11 2.964(2) 169.0 2
N12 H12 N40A 0.86 1.94 2.761(5) 159.9 .
N12 H12 N40B 0.86 2.09 2.93(2) 165.8 .
N14 H14A O36 0.86 2.30 3.054(2) 147.2 3_666
N14 H14B O18 0.86 2.27 2.795(3) 119.3 .
N14 H14B O20 0.86 2.20 2.806(2) 127.7 1_655
N24 H24A O1 0.86 2.15 2.972(2) 159.1 3_566
N24 H24B O20 0.86 2.25 2.779(2) 119.7 .
N24 H24B O36 0.86 2.39 3.176(2) 152.0 3_566
N25 H25 N37 0.86 2.10 2.950(3) 168.1 .
N30 H30 O2 0.86 2.30 2.927(2) 130.1 3_565
N32 H32A O18 0.86 2.10 2.909(3) 156.5 3_665
N32 H32B O35 0.86 2.27 2.804(3) 120.2 .
C42A H42C O35 0.96 2.50 3.027(5) 114.1 1_556

_refine_diff_density_max         0.385
_refine_diff_density_min         -0.285
_refine_diff_density_rms         0.045

####################################################################### 
# 
# 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_shrv628
_database_code_depnum_ccdc_archive 'CCDC 1848976'
_audit_update_record             
;
2018-06-12 deposited with the CCDC.
2018-08-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C6 H6 N8 O4), 3(H2 O)'
_chemical_formula_sum            'C12 H18 N16 O11'
_chemical_formula_weight         562.42

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           60
_space_group_name_H-M_alt        'P b c n'
_space_group_name_Hall           '-P 2n 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+1/2, z+1/2'
'-x, y, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'x, -y, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   10.8470(3)
_cell_length_b                   14.2197(5)
_cell_length_c                   14.3756(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2217.31(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3545
_cell_measurement_theta_min      5.129
_cell_measurement_theta_max      49.906

_exptl_crystal_description       block
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.685
_exptl_crystal_F_000             1160
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.718
_exptl_crystal_size_mid          0.214
_exptl_crystal_size_min          0.091
_exptl_absorpt_coefficient_mu    1.299
_shelx_estimated_absorpt_T_min   0.456
_shelx_estimated_absorpt_T_max   0.891
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6373
_exptl_absorpt_correction_T_max  0.7538
_exptl_absorpt_process_details   'SADABS v2014/5 (Bruker, 2008)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   '1uS microfocus'
_diffrn_radiation_monochromator  'HELIOS multilayer optics'
_diffrn_measurement_device_type  'Photon 100'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11323
_diffrn_reflns_av_unetI/netI     0.0386
_diffrn_reflns_av_R_equivalents  0.0514
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         5.128
_diffrn_reflns_theta_max         74.763
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.951
_diffrn_measured_fraction_theta_full 0.972
_diffrn_reflns_Laue_measured_fraction_max 0.951
_diffrn_reflns_Laue_measured_fraction_full 0.972
_diffrn_reflns_point_group_measured_fraction_max 0.951
_diffrn_reflns_point_group_measured_fraction_full 0.972
_reflns_number_total             2172
_reflns_number_gt                1917
_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       'Bruker APEX3 v2015.5-2 (Bruker, 2015)'
_computing_cell_refinement       'Bruker APEX3 v2015.5-2 (Bruker, 2015)'
_computing_data_reduction        
;
Bruker SAINT v8.34A (Bruker, 2013), Bruker XPREP v2014/2 (Bruker, 2014)
;
_computing_structure_solution    'Bruker SHELXTL v2014/7 (Bruker, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL v2014/7 (Bruker, 2014)'
_computing_publication_material  'Bruker SHELXTL v2014/7 (Bruker, 2014)'
_refine_special_details          
;
One pyrazole hydrogen displays two-component disorder and is alternately 
bound to N7 or N8.  Hydrogen atom occupancies on both atoms have been 
fixed at 0.5.  One water molecule (O19) is disordered around a 2-fold 
rotation axis. A second water molecule (O20) displays two-component 
disorder with a 0.6:0.4 ratio between the major and minor component.  
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0462P)²+3.3016P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0045(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2172
_refine_ls_number_parameters     182
_refine_ls_number_restraints     8
_refine_ls_R_factor_all          0.0590
_refine_ls_R_factor_gt           0.0525
_refine_ls_wR_factor_ref         0.1380
_refine_ls_wR_factor_gt          0.1328
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.046
_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 0.2578(2) 0.06340(15) -0.10904(14) 0.0529(6) Uani 1 1 d . . . . .
O2 O 0.25881(18) 0.19958(13) -0.04190(14) 0.0434(5) Uani 1 1 d . . . . .
N3 N 0.23015(19) 0.11598(15) -0.04293(15) 0.0335(5) Uani 1 1 d . . . . .
C4 C 0.1654(2) 0.07618(16) 0.03097(16) 0.0273(5) Uani 1 1 d . . . . .
C5 C 0.1408(2) -0.02130(16) 0.04133(17) 0.0286(5) Uani 1 1 d . . . . .
N6 N 0.1693(2) -0.09220(15) -0.01485(16) 0.0384(5) Uani 1 1 d . . . . .
H6A H 0.1504 -0.1488 0.0006 0.046 Uiso 1 1 d R U . . .
H6B H 0.2063 -0.0819 -0.0667 0.046 Uiso 1 1 d R U . . .
N7 N 0.0832(2) -0.03137(14) 0.12278(14) 0.0328(5) Uani 1 1 d . . . . .
H7 H 0.0576 -0.0837 0.1457 0.039 Uiso 0.5 1 calc R U P . .
N8 N 0.0712(2) 0.05494(14) 0.16405(14) 0.0327(5) Uani 1 1 d . . . . .
H8 H 0.0374 0.0654 0.2173 0.039 Uiso 0.5 1 d R U P . .
C9 C 0.1199(2) 0.12087(16) 0.11069(16) 0.0277(5) Uani 1 1 d . . . . .
C10 C 0.1222(2) 0.21915(16) 0.14184(16) 0.0280(5) Uani 1 1 d . . . . .
N11 N 0.1648(2) 0.23679(15) 0.22541(15) 0.0356(5) Uani 1 1 d . . . . .
N12 N 0.1563(2) 0.33272(14) 0.23586(15) 0.0352(5) Uani 1 1 d . . . . .
H12 H 0.1780 0.3620 0.2858 0.042 Uiso 1 1 d R U . . .
C13 C 0.1104(2) 0.37656(17) 0.16074(17) 0.0306(5) Uani 1 1 d . . . . .
N14 N 0.0933(2) 0.46870(15) 0.15515(17) 0.0397(5) Uani 1 1 d . . . . .
H14A H 0.1118 0.5045 0.2016 0.048 Uiso 1 1 d R U . . .
H14B H 0.0637 0.4927 0.1051 0.048 Uiso 1 1 d R U . . .
C15 C 0.0857(2) 0.30334(16) 0.09723(16) 0.0284(5) Uani 1 1 d . . . . .
N16 N 0.03327(19) 0.31610(14) 0.01010(14) 0.0317(5) Uani 1 1 d . . . . .
O17 O 0.00785(18) 0.24745(13) -0.03880(12) 0.0397(5) Uani 1 1 d . . . . .
O18 O 0.0157(2) 0.39837(14) -0.01671(15) 0.0514(6) Uani 1 1 d . . . . .
O19 O 0.5000 0.3318(2) 0.2500 0.0896(15) Uani 1 2 d DS T P . .
H19A H 0.4775 0.3554 0.2040 0.134 Uiso 0.5 1 d DR U P . .
H19B H 0.5000 0.2756 0.2500 0.134 Uiso 1 2 d DR U P . .
O20B O 0.3397(4) 0.1071(3) 0.2989(3) 0.0537(11) Uani 0.602(6) 1 d D . P . .
H20A H 0.3888 0.1318 0.3358 0.081 Uiso 1 1 d DR U . . .
H20B H 0.3187 0.1551 0.2693 0.081 Uiso 1 1 d DR U . . .
O20A O 0.3912(6) 0.1376(5) 0.2772(4) 0.0537(11) Uani 0.398(6) 1 d D . P . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 N3 1.246(3) . ?
O2 N3 1.229(3) . ?
N3 C4 1.394(3) . ?
C4 C9 1.400(3) . ?
C4 C5 1.419(3) . ?
C5 N6 1.328(3) . ?
C5 N7 1.335(3) . ?
N6 H6A 0.8593 . ?
N6 H6B 0.8594 . ?
N7 N8 1.369(3) . ?
N7 H7 0.8600 . ?
N8 C9 1.322(3) . ?
N8 H8 0.8611 . ?
C9 C10 1.468(3) . ?
C10 N11 1.311(3) . ?
C10 C15 1.415(3) . ?
N11 N12 1.375(3) . ?
N12 C13 1.342(3) . ?
N12 H12 0.8627 . ?
C13 N14 1.326(3) . ?
C13 C15 1.411(3) . ?
N14 H14A 0.8631 . ?
N14 H14B 0.8583 . ?
C15 N16 1.387(3) . ?
N16 O17 1.234(3) . ?
N16 O18 1.246(3) . ?
O19 H19A 0.7807 . ?
O19 H19B 0.7984 . ?
O20B O20A 0.774(6) . ?
O20B H20A 0.8298 . ?
O20B H20B 0.8360 . ?
O20A H20A 0.8477 . ?
O20A H20B 0.8326 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 N3 O1 121.9(2) . . ?
O2 N3 C4 120.7(2) . . ?
O1 N3 C4 117.3(2) . . ?
N3 C4 C9 128.1(2) . . ?
N3 C4 C5 124.8(2) . . ?
C9 C4 C5 106.9(2) . . ?
N6 C5 N7 124.1(2) . . ?
N6 C5 C4 129.3(2) . . ?
N7 C5 C4 106.5(2) . . ?
C5 N6 H6A 119.8 . . ?
C5 N6 H6B 120.5 . . ?
H6A N6 H6B 119.7 . . ?
C5 N7 N8 109.16(19) . . ?
C5 N7 H7 125.4 . . ?
N8 N7 H7 125.4 . . ?
C9 N8 N7 110.27(19) . . ?
C9 N8 H8 124.3 . . ?
N7 N8 H8 125.4 . . ?
N8 C9 C4 107.1(2) . . ?
N8 C9 C10 120.3(2) . . ?
C4 C9 C10 132.5(2) . . ?
N11 C10 C15 110.6(2) . . ?
N11 C10 C9 117.9(2) . . ?
C15 C10 C9 131.5(2) . . ?
C10 N11 N12 105.4(2) . . ?
C13 N12 N11 113.4(2) . . ?
C13 N12 H12 123.1 . . ?
N11 N12 H12 123.4 . . ?
N14 C13 N12 124.0(2) . . ?
N14 C13 C15 131.6(2) . . ?
N12 C13 C15 104.4(2) . . ?
C13 N14 H14A 120.2 . . ?
C13 N14 H14B 119.8 . . ?
H14A N14 H14B 120.0 . . ?
N16 C15 C13 124.5(2) . . ?
N16 C15 C10 129.4(2) . . ?
C13 C15 C10 106.1(2) . . ?
O17 N16 O18 122.1(2) . . ?
O17 N16 C15 120.1(2) . . ?
O18 N16 C15 117.7(2) . . ?
H19A O19 H19B 115.5 . . ?
O20A O20B H20A 63.7 . . ?
O20A O20B H20B 62.2 . . ?
H20A O20B H20B 98.9 . . ?
O20B O20A H20A 61.4 . . ?
O20B O20A H20B 62.6 . . ?
H20A O20A H20B 97.7 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 N3 C4 C9 3.2(4) . . . . ?
O1 N3 C4 C9 -177.1(2) . . . . ?
O2 N3 C4 C5 -172.3(2) . . . . ?
O1 N3 C4 C5 7.4(4) . . . . ?
N3 C4 C5 N6 -1.9(4) . . . . ?
C9 C4 C5 N6 -178.1(2) . . . . ?
N3 C4 C5 N7 176.7(2) . . . . ?
C9 C4 C5 N7 0.4(3) . . . . ?
N6 C5 N7 N8 178.3(2) . . . . ?
C4 C5 N7 N8 -0.3(3) . . . . ?
C5 N7 N8 C9 0.1(3) . . . . ?
N7 N8 C9 C4 0.2(3) . . . . ?
N7 N8 C9 C10 -177.7(2) . . . . ?
N3 C4 C9 N8 -176.4(2) . . . . ?
C5 C4 C9 N8 -0.4(3) . . . . ?
N3 C4 C9 C10 1.1(4) . . . . ?
C5 C4 C9 C10 177.2(2) . . . . ?
N8 C9 C10 N11 49.9(3) . . . . ?
C4 C9 C10 N11 -127.4(3) . . . . ?
N8 C9 C10 C15 -130.2(3) . . . . ?
C4 C9 C10 C15 52.6(4) . . . . ?
C15 C10 N11 N12 0.0(3) . . . . ?
C9 C10 N11 N12 180.0(2) . . . . ?
C10 N11 N12 C13 -0.6(3) . . . . ?
N11 N12 C13 N14 179.6(2) . . . . ?
N11 N12 C13 C15 0.9(3) . . . . ?
N14 C13 C15 N16 -0.6(4) . . . . ?
N12 C13 C15 N16 178.0(2) . . . . ?
N14 C13 C15 C10 -179.4(3) . . . . ?
N12 C13 C15 C10 -0.8(3) . . . . ?
N11 C10 C15 N16 -178.2(2) . . . . ?
C9 C10 C15 N16 1.8(4) . . . . ?
N11 C10 C15 C13 0.5(3) . . . . ?
C9 C10 C15 C13 -179.5(2) . . . . ?
C13 C15 N16 O17 -175.6(2) . . . . ?
C10 C15 N16 O17 2.9(4) . . . . ?
C13 C15 N16 O18 5.8(4) . . . . ?
C10 C15 N16 O18 -175.7(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N6 H6A O2 0.86 2.45 3.086(3) 131.6 8_655
N6 H6A O17 0.86 2.28 3.027(3) 144.7 5
N6 H6B O1 0.86 2.23 2.766(3) 120.8 .
N6 H6B O20B 0.86 2.44 3.260(6) 159.9 7
N8 H8 N8 0.86 2.08 2.914(4) 163.3 3
N12 H12 O1 0.86 1.97 2.832(3) 173.3 2
N12 H12 N3 0.86 2.67 3.487(3) 157.6 2
N14 H14A O20B 0.86 2.09 2.945(5) 171.3 8_665
N14 H14A O20A 0.86 2.18 2.979(7) 153.2 8_665
N14 H14B O18 0.86 2.27 2.795(3) 119.8 .
N14 H14B O18 0.86 2.18 2.989(3) 156.7 5_565
O19 H19A N7 0.78 2.09 2.819(3) 154.3 8_665
O19 H19B O20A 0.80 2.32 3.028(8) 147.7 .
O19 H19B O20A 0.80 2.32 3.028(8) 147.7 3_655
O20B H20A O18 0.83 2.40 3.081(4) 140.1 2
O20A H20A O18 0.85 2.40 3.172(6) 152.0 2
O20B H20B N11 0.84 2.13 2.849(4) 144.1 .
O20A H20B N11 0.83 2.13 2.929(6) 160.7 .

_refine_diff_density_max         0.303
_refine_diff_density_min         -0.253
_refine_diff_density_rms         0.059

####################################################################### 
# 
# 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_shrv614
_database_code_depnum_ccdc_archive 'CCDC 1848975'
_audit_update_record             
;
2018-06-12 deposited with the CCDC.
2018-08-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H4 N14 O8, C H3 N O2, 2(C H4 O)'
_chemical_formula_sum            'C13 H15 N15 O12'
_chemical_formula_weight         573.40

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_H-M_alt        'C c'
_space_group_name_Hall           'C -2yc'

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

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

_cell_length_a                   8.8353(2)
_cell_length_b                   18.9345(4)
_cell_length_c                   13.7810(3)
_cell_angle_alpha                90
_cell_angle_beta                 90.0620(10)
_cell_angle_gamma                90
_cell_volume                     2305.45(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    6177
_cell_measurement_theta_min      4.67
_cell_measurement_theta_max      74.59

_exptl_crystal_description       plate
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.652
_exptl_crystal_F_000             1176
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.384
_exptl_crystal_size_mid          0.263
_exptl_crystal_size_min          0.094
_exptl_absorpt_coefficient_mu    1.288
_shelx_estimated_absorpt_T_min   0.638
_shelx_estimated_absorpt_T_max   0.889
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6640
_exptl_absorpt_correction_T_max  0.7538
_exptl_absorpt_process_details   'SADABS v2014/5 (Bruker, 2008)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   '1uS microfocus'
_diffrn_radiation_monochromator  'HELIOS multilayer optics'
_diffrn_measurement_device_type  'Photon 100'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7494
_diffrn_reflns_av_unetI/netI     0.0292
_diffrn_reflns_av_R_equivalents  0.0257
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         4.671
_diffrn_reflns_theta_max         74.578
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.933
_diffrn_measured_fraction_theta_full 0.960
_diffrn_reflns_Laue_measured_fraction_max 0.933
_diffrn_reflns_Laue_measured_fraction_full 0.960
_diffrn_reflns_point_group_measured_fraction_max 0.709
_diffrn_reflns_point_group_measured_fraction_full 0.747
_reflns_number_total             3343
_reflns_number_gt                3187
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.517
_reflns_Friedel_fraction_max     0.485
_reflns_Friedel_fraction_full    0.533

_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       'Bruker APEX3 v2015.5-2 (Bruker, 2015)'
_computing_cell_refinement       'Bruker APEX3 v2015.5-2 (Bruker, 2015)'
_computing_data_reduction        
;
Bruker SAINT v8.34A (Bruker, 2013), Bruker XPREP v2014/2 (Bruker, 2014)
;
_computing_structure_solution    'Bruker SHELXTL v2014/7 (Bruker, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL v2014/7 (Bruker, 2014)'
_computing_publication_material  'Bruker SHELXTL v2014/7 (Bruker, 2014)'
_refine_special_details          
;
Aniostropic displacement parameters for nitromethane were restrained 
using enhanced rigid-bond restraints (esds = 0.001).  Bond angles and
lengths in nitromethane were restrained to literature values.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0630P)²+1.3938P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_extinction_coef       0.00161(17)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 1050 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.01(12)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3343
_refine_ls_number_parameters     371
_refine_ls_number_restraints     25
_refine_ls_R_factor_all          0.0368
_refine_ls_R_factor_gt           0.0343
_refine_ls_wR_factor_ref         0.0950
_refine_ls_wR_factor_gt          0.0923
_refine_ls_goodness_of_fit_ref   0.951
_refine_ls_restrained_S_all      0.987
_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 0.7962(3) 0.43230(14) 0.6699(2) 0.0390(7) Uani 1 1 d . . . . .
H1A H 0.741001 0.457889 0.632326 0.047 Uiso 1 1 calc R U . . .
H1B H 0.867766 0.451387 0.703112 0.047 Uiso 1 1 calc R U . . .
C2 C 0.7715(4) 0.36460(17) 0.6763(2) 0.0323(7) Uani 1 1 d . . . . .
C3 C 0.8451(4) 0.31217(18) 0.7319(2) 0.0373(7) Uani 1 1 d . . . . .
N4 N 0.9711(4) 0.33138(17) 0.7947(2) 0.0444(7) Uani 1 1 d . . . . .
O5 O 1.0080(4) 0.39361(17) 0.7976(3) 0.0639(9) Uani 1 1 d . . . . .
O6 O 1.0317(4) 0.28586(17) 0.8421(2) 0.0663(9) Uani 1 1 d . . . . .
N7 N 0.8105(4) 0.24396(16) 0.7325(2) 0.0438(7) Uani 1 1 d . . . . .
N8 N 0.6996(4) 0.21799(15) 0.6799(2) 0.0448(7) Uani 1 1 d . . . . .
C9 C 0.6209(4) 0.26497(16) 0.6249(2) 0.0355(7) Uani 1 1 d . . . . .
C10 C 0.4976(4) 0.25971(16) 0.5627(2) 0.0355(7) Uani 1 1 d . . . . .
N11 N 0.4178(4) 0.19714(15) 0.5379(2) 0.0435(7) Uani 1 1 d . . . . .
O12 O 0.4724(4) 0.14049(13) 0.5621(2) 0.0633(9) Uani 1 1 d . . . . .
O13 O 0.2986(4) 0.20256(15) 0.4932(3) 0.0612(8) Uani 1 1 d . . . . .
C14 C 0.4703(4) 0.32842(16) 0.5265(2) 0.0321(7) Uani 1 1 d . . . . .
N15 N 0.5683(3) 0.37488(13) 0.5629(2) 0.0329(6) Uani 1 1 d . . . . .
N16 N 0.6580(3) 0.33554(13) 0.6232(2) 0.0318(6) Uani 1 1 d . . . . .
C17 C 0.3675(4) 0.35470(15) 0.4513(2) 0.0321(7) Uani 1 1 d . . . . .
C18 C 0.2084(4) 0.35862(16) 0.4445(2) 0.0326(7) Uani 1 1 d . . . . .
N19 N 0.1011(4) 0.33611(16) 0.5154(2) 0.0442(7) Uani 1 1 d . . . . .
O20 O 0.1493(4) 0.32162(18) 0.5963(2) 0.0627(8) Uani 1 1 d . . . . .
O21 O -0.0325(3) 0.33342(17) 0.4926(2) 0.0572(7) Uani 1 1 d . . . . .
C22 C 0.1768(4) 0.39498(15) 0.3597(2) 0.0313(7) Uani 1 1 d . . . . .
N23 N 0.0474(3) 0.41940(16) 0.3176(2) 0.0399(7) Uani 1 1 d . . . . .
N24 N 0.0634(3) 0.45376(15) 0.2357(2) 0.0380(6) Uani 1 1 d . . . . .
C25 C 0.1963(4) 0.46189(16) 0.1933(2) 0.0341(7) Uani 1 1 d . . . . .
N26 N 0.1900(4) 0.49610(16) 0.0997(2) 0.0418(7) Uani 1 1 d . . . . .
O27 O 0.0677(4) 0.51629(15) 0.0687(2) 0.0593(8) Uani 1 1 d . . . . .
O28 O 0.3098(4) 0.50197(17) 0.0544(2) 0.0593(8) Uani 1 1 d . . . . .
C29 C 0.3368(4) 0.43944(16) 0.2319(2) 0.0319(7) Uani 1 1 d . . . . .
N30 N 0.4722(3) 0.44461(17) 0.1975(2) 0.0431(7) Uani 1 1 d . . . . .
H30A H 0.547771 0.428600 0.230099 0.052 Uiso 1 1 calc R U . . .
H30B H 0.486781 0.464058 0.141848 0.052 Uiso 1 1 calc R U . . .
N31 N 0.3160(3) 0.40835(13) 0.32042(19) 0.0310(6) Uani 1 1 d . . . . .
N32 N 0.4339(3) 0.38444(13) 0.3753(2) 0.0324(6) Uani 1 1 d . . . . .
C33 C 0.7534(7) 0.3206(3) 0.2643(5) 0.0861(17) Uani 1 1 d . . . . .
H33A H 0.853185 0.303074 0.250986 0.129 Uiso 1 1 calc R U . . .
H33B H 0.681382 0.296528 0.223897 0.129 Uiso 1 1 calc R U . . .
H33C H 0.729221 0.312537 0.331243 0.129 Uiso 1 1 calc R U . . .
O34 O 0.7483(4) 0.3909(2) 0.2454(4) 0.0812(11) Uani 1 1 d D . . . .
H34 H 0.821(6) 0.407(4) 0.276(5) 0.122 Uiso 1 1 d D U . . .
C35 C 0.7258(6) 0.5184(3) 0.4427(3) 0.0632(12) Uani 1 1 d . . . . .
H35A H 0.711731 0.558534 0.401004 0.095 Uiso 1 1 calc R U . . .
H35B H 0.658444 0.481246 0.423257 0.095 Uiso 1 1 calc R U . . .
H35C H 0.828509 0.502304 0.438049 0.095 Uiso 1 1 calc R U . . .
O36 O 0.6943(3) 0.53797(14) 0.5396(2) 0.0493(7) Uani 1 1 d D . . . .
H36 H 0.752(5) 0.5715(19) 0.543(4) 0.074 Uiso 1 1 d D U . . .
C37 C 0.3646(8) 0.3454(4) 0.9456(5) 0.0971(19) Uani 1 1 d D . . . .
H37A H 0.439981 0.356555 0.993451 0.146 Uiso 1 1 calc R U . . .
H37B H 0.335154 0.296848 0.952218 0.146 Uiso 1 1 calc R U . . .
H37C H 0.277885 0.375188 0.954803 0.146 Uiso 1 1 calc R U . . .
N38 N 0.4262(6) 0.3569(3) 0.8497(4) 0.1004(15) Uani 1 1 d D . . . .
O39 O 0.5170(9) 0.3127(4) 0.8249(6) 0.170(3) Uani 1 1 d D . . . .
O40 O 0.3919(11) 0.4099(5) 0.8087(8) 0.246(6) Uani 1 1 d D . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C2 1.303(4) . ?
N1 H1A 0.8600 . ?
N1 H1B 0.8600 . ?
C2 N16 1.357(4) . ?
C2 C3 1.413(5) . ?
C3 N7 1.327(5) . ?
C3 N4 1.455(5) . ?
N4 O6 1.206(4) . ?
N4 O5 1.223(4) . ?
N7 N8 1.314(5) . ?
N8 C9 1.360(5) . ?
C9 N16 1.376(4) . ?
C9 C10 1.389(5) . ?
C10 C14 1.414(4) . ?
C10 N11 1.420(4) . ?
N11 O12 1.222(4) . ?
N11 O13 1.225(4) . ?
C14 N15 1.332(4) . ?
C14 C17 1.464(5) . ?
N15 N16 1.369(4) . ?
C17 N32 1.326(4) . ?
C17 C18 1.411(5) . ?
C18 C22 1.385(5) . ?
C18 N19 1.427(4) . ?
N19 O21 1.222(4) . ?
N19 O20 1.224(4) . ?
C22 N23 1.363(4) . ?
C22 N31 1.368(4) . ?
N23 N24 1.310(4) . ?
N24 C25 1.321(4) . ?
C25 C29 1.416(4) . ?
C25 N26 1.444(4) . ?
N26 O27 1.222(4) . ?
N26 O28 1.235(4) . ?
C29 N30 1.291(4) . ?
C29 N31 1.367(4) . ?
N30 H30A 0.8600 . ?
N30 H30B 0.8600 . ?
N31 N32 1.364(4) . ?
C33 O34 1.357(7) . ?
C33 H33A 0.9600 . ?
C33 H33B 0.9600 . ?
C33 H33C 0.9600 . ?
O34 H34 0.829(13) . ?
C35 O36 1.413(5) . ?
C35 H35A 0.9600 . ?
C35 H35B 0.9600 . ?
C35 H35C 0.9600 . ?
O36 H36 0.817(13) . ?
C37 N38 1.446(7) . ?
C37 H37A 0.9600 . ?
C37 H37B 0.9600 . ?
C37 H37C 0.9600 . ?
N38 O40 1.191(5) . ?
N38 O39 1.209(5) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 N1 H1A 120.0 . . ?
C2 N1 H1B 120.0 . . ?
H1A N1 H1B 120.0 . . ?
N1 C2 N16 119.1(3) . . ?
N1 C2 C3 130.6(3) . . ?
N16 C2 C3 110.3(3) . . ?
N7 C3 C2 125.5(3) . . ?
N7 C3 N4 114.6(3) . . ?
C2 C3 N4 119.9(3) . . ?
O6 N4 O5 123.5(3) . . ?
O6 N4 C3 118.8(3) . . ?
O5 N4 C3 117.7(3) . . ?
N8 N7 C3 122.2(3) . . ?
N7 N8 C9 116.3(3) . . ?
N8 C9 N16 121.5(3) . . ?
N8 C9 C10 134.2(3) . . ?
N16 C9 C10 104.3(3) . . ?
C9 C10 C14 106.6(3) . . ?
C9 C10 N11 126.6(3) . . ?
C14 C10 N11 126.7(3) . . ?
O12 N11 O13 123.4(3) . . ?
O12 N11 C10 118.1(3) . . ?
O13 N11 C10 118.5(3) . . ?
N15 C14 C10 111.3(3) . . ?
N15 C14 C17 116.4(3) . . ?
C10 C14 C17 131.9(3) . . ?
C14 N15 N16 104.2(2) . . ?
C2 N16 N15 122.3(2) . . ?
C2 N16 C9 124.1(3) . . ?
N15 N16 C9 113.6(3) . . ?
N32 C17 C18 111.5(3) . . ?
N32 C17 C14 115.4(3) . . ?
C18 C17 C14 133.0(3) . . ?
C22 C18 C17 106.4(3) . . ?
C22 C18 N19 126.4(3) . . ?
C17 C18 N19 127.0(3) . . ?
O21 N19 O20 124.1(3) . . ?
O21 N19 C18 118.6(3) . . ?
O20 N19 C18 117.3(3) . . ?
N23 C22 N31 121.5(3) . . ?
N23 C22 C18 134.1(3) . . ?
N31 C22 C18 104.2(3) . . ?
N24 N23 C22 116.3(3) . . ?
N23 N24 C25 122.4(3) . . ?
N24 C25 C29 125.3(3) . . ?
N24 C25 N26 114.4(3) . . ?
C29 C25 N26 120.2(3) . . ?
O27 N26 O28 123.6(3) . . ?
O27 N26 C25 119.0(3) . . ?
O28 N26 C25 117.3(3) . . ?
N30 C29 N31 119.1(3) . . ?
N30 C29 C25 130.6(3) . . ?
N31 C29 C25 110.3(3) . . ?
C29 N30 H30A 120.0 . . ?
C29 N30 H30B 120.0 . . ?
H30A N30 H30B 120.0 . . ?
N32 N31 C29 122.3(3) . . ?
N32 N31 C22 113.9(3) . . ?
C29 N31 C22 123.7(3) . . ?
C17 N32 N31 103.9(3) . . ?
O34 C33 H33A 109.5 . . ?
O34 C33 H33B 109.5 . . ?
H33A C33 H33B 109.5 . . ?
O34 C33 H33C 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?
C33 O34 H34 103(5) . . ?
O36 C35 H35A 109.5 . . ?
O36 C35 H35B 109.5 . . ?
H35A C35 H35B 109.5 . . ?
O36 C35 H35C 109.5 . . ?
H35A C35 H35C 109.5 . . ?
H35B C35 H35C 109.5 . . ?
C35 O36 H36 98(4) . . ?
N38 C37 H37A 109.5 . . ?
N38 C37 H37B 109.5 . . ?
H37A C37 H37B 109.5 . . ?
N38 C37 H37C 109.5 . . ?
H37A C37 H37C 109.5 . . ?
H37B C37 H37C 109.5 . . ?
O40 N38 O39 128.1(9) . . ?
O40 N38 C37 117.7(8) . . ?
O39 N38 C37 113.9(7) . . ?

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
N1 C2 C3 N7 -179.6(4) . . . . ?
N16 C2 C3 N7 0.5(5) . . . . ?
N1 C2 C3 N4 -0.1(6) . . . . ?
N16 C2 C3 N4 180.0(3) . . . . ?
N7 C3 N4 O6 -1.0(5) . . . . ?
C2 C3 N4 O6 179.5(4) . . . . ?
N7 C3 N4 O5 -179.7(4) . . . . ?
C2 C3 N4 O5 0.8(5) . . . . ?
C2 C3 N7 N8 -0.5(6) . . . . ?
N4 C3 N7 N8 179.9(3) . . . . ?
C3 N7 N8 C9 -0.3(5) . . . . ?
N7 N8 C9 N16 1.2(5) . . . . ?
N7 N8 C9 C10 -178.4(4) . . . . ?
N8 C9 C10 C14 -179.5(4) . . . . ?
N16 C9 C10 C14 0.8(4) . . . . ?
N8 C9 C10 N11 -1.4(7) . . . . ?
N16 C9 C10 N11 179.0(3) . . . . ?
C9 C10 N11 O12 -10.6(6) . . . . ?
C14 C10 N11 O12 167.1(4) . . . . ?
C9 C10 N11 O13 169.7(4) . . . . ?
C14 C10 N11 O13 -12.5(6) . . . . ?
C9 C10 C14 N15 -0.3(4) . . . . ?
N11 C10 C14 N15 -178.4(3) . . . . ?
C9 C10 C14 C17 172.5(4) . . . . ?
N11 C10 C14 C17 -5.7(6) . . . . ?
C10 C14 N15 N16 -0.4(4) . . . . ?
C17 C14 N15 N16 -174.4(3) . . . . ?
N1 C2 N16 N15 0.0(5) . . . . ?
C3 C2 N16 N15 179.9(3) . . . . ?
N1 C2 N16 C9 -179.5(3) . . . . ?
C3 C2 N16 C9 0.5(4) . . . . ?
C14 N15 N16 C2 -178.5(3) . . . . ?
C14 N15 N16 C9 1.0(4) . . . . ?
N8 C9 N16 C2 -1.3(5) . . . . ?
C10 C9 N16 C2 178.4(3) . . . . ?
N8 C9 N16 N15 179.1(3) . . . . ?
C10 C9 N16 N15 -1.2(4) . . . . ?
N15 C14 C17 N32 55.2(4) . . . . ?
C10 C14 C17 N32 -117.2(4) . . . . ?
N15 C14 C17 C18 -120.7(4) . . . . ?
C10 C14 C17 C18 66.9(5) . . . . ?
N32 C17 C18 C22 -1.7(4) . . . . ?
C14 C17 C18 C22 174.4(3) . . . . ?
N32 C17 C18 N19 -175.9(3) . . . . ?
C14 C17 C18 N19 0.1(5) . . . . ?
C22 C18 N19 O21 17.7(5) . . . . ?
C17 C18 N19 O21 -169.2(3) . . . . ?
C22 C18 N19 O20 -161.3(3) . . . . ?
C17 C18 N19 O20 11.9(5) . . . . ?
C17 C18 C22 N23 -174.6(3) . . . . ?
N19 C18 C22 N23 -0.3(6) . . . . ?
C17 C18 C22 N31 1.7(3) . . . . ?
N19 C18 C22 N31 176.0(3) . . . . ?
N31 C22 N23 N24 2.7(4) . . . . ?
C18 C22 N23 N24 178.5(3) . . . . ?
C22 N23 N24 C25 3.0(5) . . . . ?
N23 N24 C25 C29 -4.2(5) . . . . ?
N23 N24 C25 N26 175.1(3) . . . . ?
N24 C25 N26 O27 2.1(4) . . . . ?
C29 C25 N26 O27 -178.5(3) . . . . ?
N24 C25 N26 O28 -176.5(3) . . . . ?
C29 C25 N26 O28 2.9(5) . . . . ?
N24 C25 C29 N30 -179.9(3) . . . . ?
N26 C25 C29 N30 0.9(5) . . . . ?
N24 C25 C29 N31 -0.5(4) . . . . ?
N26 C25 C29 N31 -179.7(3) . . . . ?
N30 C29 N31 N32 2.1(4) . . . . ?
C25 C29 N31 N32 -177.4(3) . . . . ?
N30 C29 N31 C22 -174.3(3) . . . . ?
C25 C29 N31 C22 6.2(4) . . . . ?
N23 C22 N31 N32 175.6(3) . . . . ?
C18 C22 N31 N32 -1.4(3) . . . . ?
N23 C22 N31 C29 -7.7(4) . . . . ?
C18 C22 N31 C29 175.3(3) . . . . ?
C18 C17 N32 N31 0.8(3) . . . . ?
C14 C17 N32 N31 -176.0(2) . . . . ?
C29 N31 N32 C17 -176.4(3) . . . . ?
C22 N31 N32 C17 0.4(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1A O36 0.86 2.03 2.834(4) 156.4 .
N1 H1B O5 0.86 2.10 2.671(4) 122.9 .
N1 H1B N24 0.86 2.53 3.323(4) 153.3 2_665
N30 H30A O34 0.86 1.92 2.724(5) 154.6 .
N30 H30B O28 0.86 2.10 2.668(4) 123.1 .
N30 H30B O36 0.86 2.31 2.950(4) 130.9 2_564
C33 H33C O6 0.96 2.56 3.009(7) 109.0 4_454
O34 H34 N23 0.829(13) 2.09(3) 2.873(4) 157(8) 1_655
O34 H34 N24 0.829(13) 2.39(6) 3.031(4) 135(7) 1_655
O36 H36 O12 0.817(13) 2.36(2) 3.146(4) 163(5) 3
O36 H36 O13 0.817(13) 2.61(3) 3.312(4) 145(5) 3

_refine_diff_density_max         0.291
_refine_diff_density_min         -0.181
_refine_diff_density_rms         0.040

