# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry A.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_shrv404
_database_code_depnum_ccdc_archive 'CCDC 1480143'
_audit_update_record             
;
2016-05-17 deposited with the CCDC.
2016-08-19 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         '[C4 N10 H5 O2][N O H4]'
_chemical_formula_sum            'C4 H9 N11 O3'
_chemical_formula_weight         259.22

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                   10.0682(5)
_cell_length_b                   9.9430(5)
_cell_length_c                   10.5715(6)
_cell_angle_alpha                90
_cell_angle_beta                 97.5240(10)
_cell_angle_gamma                90
_cell_volume                     1049.18(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    8129
_cell_measurement_theta_min      2.824
_cell_measurement_theta_max      29.998

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.641
_exptl_crystal_F_000             536
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.444
_exptl_crystal_size_mid          0.418
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    0.139
_shelx_estimated_absorpt_T_min   0.941
_shelx_estimated_absorpt_T_max   0.992
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7063
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_process_details   'SADABS v2014/5 (Bruker, 2008)'
_diffrn_ambient_temperature      150(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            10921
_diffrn_reflns_av_unetI/netI     0.0124
_diffrn_reflns_av_R_equivalents  0.0159
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.824
_diffrn_reflns_theta_max         28.695
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2708
_reflns_number_gt                2517
_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          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0533P)²+0.3190P] 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         2708
_refine_ls_number_parameters     165
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0334
_refine_ls_R_factor_gt           0.0313
_refine_ls_wR_factor_ref         0.0887
_refine_ls_wR_factor_gt          0.0859
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_restrained_S_all      1.054
_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 0.28730(7) 0.10178(7) -0.07095(7) 0.02029(16) Uani 1 1 d . . . . .
O2 O 0.47718(6) 0.17578(7) -0.12375(6) 0.01750(15) Uani 1 1 d . . . . .
N3 N 0.37394(7) 0.19478(8) -0.06732(7) 0.01378(16) Uani 1 1 d . . . . .
N4 N 0.36566(7) 0.30930(8) -0.01046(7) 0.01470(16) Uani 1 1 d . . . . .
C5 C 0.24946(8) 0.33212(9) 0.04287(8) 0.01275(17) Uani 1 1 d . . . . .
N6 N 0.13248(7) 0.26545(8) 0.03150(7) 0.01473(16) Uani 1 1 d . . . . .
H6 H 0.1159 0.1899 -0.0110 0.018 Uiso 1 1 calc R U . . .
N7 N 0.04263(7) 0.33228(8) 0.09566(7) 0.01588(17) Uani 1 1 d . . . . .
C8 C 0.11412(8) 0.43574(9) 0.14459(8) 0.01313(17) Uani 1 1 d . . . . .
N9 N 0.24140(7) 0.44125(8) 0.11546(7) 0.01439(16) Uani 1 1 d . . . . .
C10 C 0.06072(9) 0.54202(9) 0.22553(9) 0.01488(18) Uani 1 1 d . . . . .
H10B H 0.1307 0.5665 0.2965 0.018 Uiso 1 1 calc R U . . .
H10A H 0.0381 0.6236 0.1734 0.018 Uiso 1 1 calc R U . . .
N11 N -0.05786(7) 0.49520(8) 0.27735(7) 0.01386(16) Uani 1 1 d . . . . .
N12 N -0.17947(8) 0.53166(9) 0.23023(8) 0.01861(18) Uani 1 1 d . . . . .
N13 N -0.26201(8) 0.46321(9) 0.29430(8) 0.01998(18) Uani 1 1 d . . . . .
C14 C -0.18293(9) 0.38531(9) 0.37961(9) 0.01569(18) Uani 1 1 d . . . . .
N15 N -0.05286(8) 0.40351(8) 0.37117(7) 0.01525(16) Uani 1 1 d . . . . .
N16 N -0.22997(9) 0.30092(10) 0.46329(9) 0.0255(2) Uani 1 1 d . . . . .
H16A H -0.1738 0.2538 0.5166 0.031 Uiso 1 1 calc R U . . .
H16B H -0.3168 0.2930 0.4645 0.031 Uiso 1 1 calc R U . . .
O17 O 0.58529(8) 0.38205(7) 0.66057(7) 0.02272(17) Uani 1 1 d . . . . .
H17 H 0.6207 0.4480 0.6283 0.034 Uiso 1 1 calc R U . . .
N18 N 0.52945(8) 0.42474(8) 0.77019(7) 0.01579(17) Uani 1 1 d . . . . .
H18A H 0.5906 0.4751 0.8206 0.024 Uiso 1 1 calc R U . . .
H18B H 0.5070 0.3515 0.8145 0.024 Uiso 1 1 calc R U . . .
H18C H 0.4549 0.4750 0.7458 0.024 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 N3 1.2684(10) . ?
O2 N3 1.2783(9) . ?
N3 N4 1.2954(11) . ?
N4 C5 1.3824(11) . ?
C5 N9 1.3376(11) . ?
C5 N6 1.3432(11) . ?
N6 N7 1.3714(10) . ?
N6 H6 0.8800 . ?
N7 C8 1.3215(12) . ?
C8 N9 1.3576(11) . ?
C8 C10 1.5028(12) . ?
C10 N11 1.4538(11) . ?
C10 H10B 0.9900 . ?
C10 H10A 0.9900 . ?
N11 N12 1.3111(10) . ?
N11 N15 1.3433(11) . ?
N12 N13 1.3266(11) . ?
N13 C14 1.3635(12) . ?
C14 N15 1.3365(11) . ?
C14 N16 1.3493(12) . ?
N16 H16A 0.8800 . ?
N16 H16B 0.8800 . ?
O17 N18 1.4176(10) . ?
O17 H17 0.8400 . ?
N18 H18A 0.9100 . ?
N18 H18B 0.9100 . ?
N18 H18C 0.9100 . ?

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 118.43(7) . . ?
O1 N3 N4 124.69(7) . . ?
O2 N3 N4 116.88(7) . . ?
N3 N4 C5 116.29(7) . . ?
N9 C5 N6 109.47(8) . . ?
N9 C5 N4 119.03(8) . . ?
N6 C5 N4 131.42(8) . . ?
C5 N6 N7 110.12(7) . . ?
C5 N6 H6 124.9 . . ?
N7 N6 H6 124.9 . . ?
C8 N7 N6 102.13(7) . . ?
N7 C8 N9 115.12(8) . . ?
N7 C8 C10 123.58(8) . . ?
N9 C8 C10 121.30(8) . . ?
C5 N9 C8 103.14(7) . . ?
N11 C10 C8 111.23(7) . . ?
N11 C10 H10B 109.4 . . ?
C8 C10 H10B 109.4 . . ?
N11 C10 H10A 109.4 . . ?
C8 C10 H10A 109.4 . . ?
H10B C10 H10A 108.0 . . ?
N12 N11 N15 114.27(7) . . ?
N12 N11 C10 122.72(7) . . ?
N15 N11 C10 122.84(7) . . ?
N11 N12 N13 106.29(7) . . ?
N12 N13 C14 106.18(7) . . ?
N15 C14 N16 123.99(8) . . ?
N15 C14 N13 111.80(8) . . ?
N16 C14 N13 124.21(8) . . ?
C14 N15 N11 101.47(7) . . ?
C14 N16 H16A 120.0 . . ?
C14 N16 H16B 120.0 . . ?
H16A N16 H16B 120.0 . . ?
N18 O17 H17 109.5 . . ?
O17 N18 H18A 109.5 . . ?
O17 N18 H18B 109.5 . . ?
H18A N18 H18B 109.5 . . ?
O17 N18 H18C 109.5 . . ?
H18A N18 H18C 109.5 . . ?
H18B N18 H18C 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 N4 C5 -3.92(13) . . . . ?
O2 N3 N4 C5 175.84(7) . . . . ?
N3 N4 C5 N9 172.27(8) . . . . ?
N3 N4 C5 N6 -11.25(14) . . . . ?
N9 C5 N6 N7 1.19(10) . . . . ?
N4 C5 N6 N7 -175.53(9) . . . . ?
C5 N6 N7 C8 -1.20(9) . . . . ?
N6 N7 C8 N9 0.85(10) . . . . ?
N6 N7 C8 C10 -179.88(8) . . . . ?
N6 C5 N9 C8 -0.62(10) . . . . ?
N4 C5 N9 C8 176.57(7) . . . . ?
N7 C8 N9 C5 -0.17(10) . . . . ?
C10 C8 N9 C5 -179.47(8) . . . . ?
N7 C8 C10 N11 19.03(12) . . . . ?
N9 C8 C10 N11 -161.74(8) . . . . ?
C8 C10 N11 N12 -102.39(10) . . . . ?
C8 C10 N11 N15 72.56(10) . . . . ?
N15 N11 N12 N13 0.36(11) . . . . ?
C10 N11 N12 N13 175.70(8) . . . . ?
N11 N12 N13 C14 -0.37(10) . . . . ?
N12 N13 C14 N15 0.29(11) . . . . ?
N12 N13 C14 N16 179.72(9) . . . . ?
N16 C14 N15 N11 -179.51(9) . . . . ?
N13 C14 N15 N11 -0.07(10) . . . . ?
N12 N11 N15 C14 -0.18(10) . . . . ?
C10 N11 N15 C14 -175.51(8) . . . . ?

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 H6 O1 0.88 2.11 2.5871(10) 113.6 .
N6 H6 N15 0.88 2.18 2.8894(11) 137.5 4_565
C10 H10B O1 0.99 2.58 3.2545(12) 125.1 4_566
N16 H16A N7 0.88 2.39 3.1999(12) 153.6 4_566
N16 H16B O2 0.88 2.18 2.9805(11) 150.7 4_466
N16 H16B O17 0.88 2.57 3.0784(12) 117.9 1_455
O17 H17 O1 0.84 1.93 2.7631(10) 174.2 2_655
O17 H17 O2 0.84 2.47 3.0021(10) 122.3 2_655
O17 H17 N3 0.84 2.54 3.3038(11) 151.8 2_655
N18 H18A N9 0.91 1.93 2.7981(11) 159.9 3_666
N18 H18B O2 0.91 1.90 2.7958(11) 166.4 1_556
N18 H18B N3 0.91 2.49 3.3666(11) 160.7 1_556
N18 H18B N4 0.91 2.51 3.2273(11) 135.7 1_556
N18 H18C N13 0.91 2.03 2.9114(11) 163.1 3_566

_refine_diff_density_max         0.284
_refine_diff_density_min         -0.350
_refine_diff_density_rms         0.078

# start Validation Reply Form
_vrf_PLAT015_shrv404             
;
PROBLEM: No _shelx_hkl_file record in SHELXL20xy CIF ....     Please Do ! 
RESPONSE: It is our policy to routinely not supply the HKL file unless 
specifically required.
;
# end Validation Reply Form
####################################################################### 
# 
# 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_shrv406
_database_code_depnum_ccdc_archive 'CCDC 1480144'
_audit_update_record             
;
2016-05-17 deposited with the CCDC.
2016-08-19 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         'C4 H3 N11 O4, 2(H4 N O), H2 O'
_chemical_formula_sum            'C4 H13 N13 O7'
_chemical_formula_weight         355.27

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                   3.8438(8)
_cell_length_b                   14.463(3)
_cell_length_c                   23.861(5)
_cell_angle_alpha                90
_cell_angle_beta                 90.988(3)
_cell_angle_gamma                90
_cell_volume                     1326.3(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    1551
_cell_measurement_theta_min      2.923
_cell_measurement_theta_max      27.9935

_exptl_crystal_description       needle
_exptl_crystal_colour            white
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.779
_exptl_crystal_F_000             736
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.040
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    0.162
_shelx_estimated_absorpt_T_min   0.965
_shelx_estimated_absorpt_T_max   0.994
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5637
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_process_details   'SADABS v2014/5 (Bruker, 2008)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(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            14056
_diffrn_reflns_av_unetI/netI     0.1325
_diffrn_reflns_av_R_equivalents  0.1177
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_theta_min         1.707
_diffrn_reflns_theta_max         29.992
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3749
_reflns_number_gt                1880
_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          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0545P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3749
_refine_ls_number_parameters     227
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.1541
_refine_ls_R_factor_gt           0.0610
_refine_ls_wR_factor_ref         0.1363
_refine_ls_wR_factor_gt          0.1097
_refine_ls_goodness_of_fit_ref   0.970
_refine_ls_restrained_S_all      0.969
_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 1.0552(5) 0.30724(13) 0.41933(8) 0.0200(5) Uani 1 1 d . . . . .
O2 O 1.1175(5) 0.35591(13) 0.33325(8) 0.0207(5) Uani 1 1 d . . . . .
N3 N 0.9910(6) 0.36449(16) 0.38083(10) 0.0165(5) Uani 1 1 d . . . . .
N4 N 0.7840(5) 0.43402(15) 0.39455(9) 0.0152(5) Uani 1 1 d . . . . .
C5 C 0.7079(6) 0.49785(19) 0.35336(11) 0.0137(6) Uani 1 1 d . . . . .
N6 N 0.7845(6) 0.50335(15) 0.29896(9) 0.0142(5) Uani 1 1 d . . . . .
H6 H 0.9097 0.4626 0.2808 0.017 Uiso 1 1 calc R U . . .
N7 N 0.6408(5) 0.58129(15) 0.27551(10) 0.0142(5) Uani 1 1 d . . . . .
C8 C 0.4852(7) 0.61965(18) 0.31836(11) 0.0124(6) Uani 1 1 d . . . . .
N9 N 0.5154(5) 0.57164(16) 0.36737(10) 0.0152(5) Uani 1 1 d . . . . .
C10 C 0.2809(7) 0.70732(18) 0.31415(12) 0.0148(6) Uani 1 1 d . . . . .
H10B H 0.1546 0.7087 0.2776 0.018 Uiso 1 1 calc R U . . .
H10A H 0.1057 0.7081 0.3441 0.018 Uiso 1 1 calc R U . . .
N11 N 0.4979(5) 0.79042(15) 0.31914(9) 0.0130(5) Uani 1 1 d . . . . .
N12 N 0.6183(6) 0.83202(16) 0.27282(10) 0.0160(5) Uani 1 1 d . . . . .
N13 N 0.8009(6) 0.90173(15) 0.29012(10) 0.0170(5) Uani 1 1 d . . . . .
N14 N 0.8038(6) 0.90743(15) 0.34732(10) 0.0162(5) Uani 1 1 d . . . . .
C15 C 0.6115(6) 0.83671(18) 0.36520(11) 0.0121(6) Uani 1 1 d . . . . .
N16 N 0.5158(6) 0.80222(16) 0.41597(10) 0.0171(5) Uani 1 1 d . . . . .
N17 N 0.6184(6) 0.85075(16) 0.46022(10) 0.0168(5) Uani 1 1 d . . . . .
O18 O 0.7908(5) 0.92278(13) 0.45869(9) 0.0253(5) Uani 1 1 d . . . . .
O19 O 0.5323(5) 0.81619(13) 0.50725(8) 0.0205(5) Uani 1 1 d . . . . .
N20 N 0.5038(5) 0.37774(15) 0.49875(10) 0.0161(5) Uani 1 1 d . . . . .
H20C H 0.2913 0.3992 0.5088 0.024 Uiso 1 1 calc R U . . .
H20B H 0.5101 0.3152 0.5029 0.024 Uiso 1 1 calc R U . . .
H20A H 0.5427 0.3926 0.4623 0.024 Uiso 1 1 calc R U . . .
O21 O 0.7644(5) 0.41846(14) 0.53340(8) 0.0198(5) Uani 1 1 d . . . . .
H21 H 0.7007 0.4174 0.5669 0.030 Uiso 1 1 calc R U . . .
N22 N 0.9406(6) 0.10562(16) 0.41453(10) 0.0197(6) Uani 1 1 d . . . . .
H22C H 1.0533 0.1490 0.4356 0.030 Uiso 1 1 calc R U . . .
H22B H 0.7965 0.0723 0.4367 0.030 Uiso 1 1 calc R U . . .
H22A H 0.8134 0.1340 0.3870 0.030 Uiso 1 1 calc R U . . .
O23 O 1.1856(5) 0.04621(15) 0.39028(10) 0.0279(5) Uani 1 1 d . . . . .
H23 H 1.0843 -0.0013 0.3781 0.042 Uiso 1 1 calc R U . . .
O24 O 0.4162(6) 0.81155(15) 0.67379(10) 0.0323(6) Uani 1 1 d D . . . .
H24B H 0.533(7) 0.7632(12) 0.6743(15) 0.039 Uiso 1 1 d D U . . .
H24A H 0.547(7) 0.8539(14) 0.6847(15) 0.039 Uiso 1 1 d D 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 N3 1.258(3) . ?
O2 N3 1.249(3) . ?
N3 N4 1.327(3) . ?
N4 C5 1.376(3) . ?
C5 N6 1.338(3) . ?
C5 N9 1.344(3) . ?
N6 N7 1.370(3) . ?
N6 H6 0.8800 . ?
N7 C8 1.316(3) . ?
C8 N9 1.363(3) . ?
C8 C10 1.494(4) . ?
C10 N11 1.467(3) . ?
C10 H10B 0.9900 . ?
C10 H10A 0.9900 . ?
N11 N12 1.347(3) . ?
N11 C15 1.353(3) . ?
N12 N13 1.292(3) . ?
N13 N14 1.367(3) . ?
N14 C15 1.336(3) . ?
C15 N16 1.366(3) . ?
N16 N17 1.322(3) . ?
N17 O18 1.236(3) . ?
N17 O19 1.277(3) . ?
N20 O21 1.416(3) . ?
N20 H20C 0.9100 . ?
N20 H20B 0.9100 . ?
N20 H20A 0.9100 . ?
O21 H21 0.8400 . ?
N22 O23 1.407(3) . ?
N22 H22C 0.9100 . ?
N22 H22B 0.9100 . ?
N22 H22A 0.9100 . ?
O23 H23 0.8400 . ?
O24 H24B 0.831(10) . ?
O24 H24A 0.831(10) . ?

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 121.6(2) . . ?
O2 N3 N4 123.0(2) . . ?
O1 N3 N4 115.5(2) . . ?
N3 N4 C5 117.0(2) . . ?
N6 C5 N9 109.0(2) . . ?
N6 C5 N4 133.2(3) . . ?
N9 C5 N4 117.8(2) . . ?
C5 N6 N7 110.6(2) . . ?
C5 N6 H6 124.7 . . ?
N7 N6 H6 124.7 . . ?
C8 N7 N6 102.4(2) . . ?
N7 C8 N9 114.7(2) . . ?
N7 C8 C10 123.4(2) . . ?
N9 C8 C10 121.8(2) . . ?
C5 N9 C8 103.3(2) . . ?
N11 C10 C8 113.1(2) . . ?
N11 C10 H10B 109.0 . . ?
C8 C10 H10B 109.0 . . ?
N11 C10 H10A 109.0 . . ?
C8 C10 H10A 109.0 . . ?
H10B C10 H10A 107.8 . . ?
N12 N11 C15 109.6(2) . . ?
N12 N11 C10 120.2(2) . . ?
C15 N11 C10 130.3(2) . . ?
N13 N12 N11 106.2(2) . . ?
N12 N13 N14 111.2(2) . . ?
C15 N14 N13 106.1(2) . . ?
N14 C15 N11 107.0(2) . . ?
N14 C15 N16 136.2(2) . . ?
N11 C15 N16 116.8(2) . . ?
N17 N16 C15 115.7(2) . . ?
O18 N17 O19 120.2(2) . . ?
O18 N17 N16 125.2(2) . . ?
O19 N17 N16 114.6(2) . . ?
O21 N20 H20C 109.5 . . ?
O21 N20 H20B 109.5 . . ?
H20C N20 H20B 109.5 . . ?
O21 N20 H20A 109.5 . . ?
H20C N20 H20A 109.5 . . ?
H20B N20 H20A 109.5 . . ?
N20 O21 H21 109.5 . . ?
O23 N22 H22C 109.5 . . ?
O23 N22 H22B 109.5 . . ?
H22C N22 H22B 109.5 . . ?
O23 N22 H22A 109.5 . . ?
H22C N22 H22A 109.5 . . ?
H22B N22 H22A 109.5 . . ?
N22 O23 H23 109.5 . . ?
H24B O24 H24A 107(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
O2 N3 N4 C5 0.6(3) . . . . ?
O1 N3 N4 C5 -179.9(2) . . . . ?
N3 N4 C5 N6 4.4(4) . . . . ?
N3 N4 C5 N9 -176.2(2) . . . . ?
N9 C5 N6 N7 -0.4(3) . . . . ?
N4 C5 N6 N7 179.0(3) . . . . ?
C5 N6 N7 C8 0.6(3) . . . . ?
N6 N7 C8 N9 -0.6(3) . . . . ?
N6 N7 C8 C10 -178.8(2) . . . . ?
N6 C5 N9 C8 0.1(3) . . . . ?
N4 C5 N9 C8 -179.5(2) . . . . ?
N7 C8 N9 C5 0.4(3) . . . . ?
C10 C8 N9 C5 178.6(2) . . . . ?
N7 C8 C10 N11 -84.5(3) . . . . ?
N9 C8 C10 N11 97.4(3) . . . . ?
C8 C10 N11 N12 93.6(3) . . . . ?
C8 C10 N11 C15 -85.9(3) . . . . ?
C15 N11 N12 N13 0.1(3) . . . . ?
C10 N11 N12 N13 -179.5(2) . . . . ?
N11 N12 N13 N14 -0.1(3) . . . . ?
N12 N13 N14 C15 0.1(3) . . . . ?
N13 N14 C15 N11 0.0(3) . . . . ?
N13 N14 C15 N16 178.6(3) . . . . ?
N12 N11 C15 N14 0.0(3) . . . . ?
C10 N11 C15 N14 179.4(2) . . . . ?
N12 N11 C15 N16 -179.0(2) . . . . ?
C10 N11 C15 N16 0.5(4) . . . . ?
N14 C15 N16 N17 4.0(4) . . . . ?
N11 C15 N16 N17 -177.4(2) . . . . ?
C15 N16 N17 O18 -0.3(4) . . . . ?
C15 N16 N17 O19 -178.6(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 H6 O2 0.88 2.13 2.611(3) 113.4 .
N6 H6 N13 0.88 2.22 3.055(3) 157.8 2_745
N20 H20B N16 0.91 2.58 3.305(3) 137.3 3_666
N20 H20B N17 0.91 2.61 3.481(3) 161.2 3_666
N20 H20B O19 0.91 1.92 2.812(3) 165.2 3_666
N20 H20A N3 0.91 2.65 3.412(3) 141.6 .
N20 H20A N4 0.91 1.97 2.845(3) 160.5 .
O21 H21 N9 0.84 1.79 2.621(3) 167.7 3_666
N22 H22C O1 0.91 2.32 2.951(3) 126.2 .
N22 H22C O19 0.91 2.14 2.956(3) 149.0 3_766
N22 H22B O18 0.91 2.23 2.908(3) 131.3 1_545
N22 H22A O24 0.91 1.86 2.767(3) 174.8 3_666
O23 H23 N14 0.84 1.85 2.680(3) 170.4 1_545
O24 H24B O2 0.831(10) 2.194(12) 3.019(3) 172(4) 3_766
O24 H24A N7 0.831(10) 2.38(3) 2.994(3) 131(3) 4_576
O24 H24A O23 0.831(10) 2.53(3) 2.999(3) 117(3) 3_766

_refine_diff_density_max         0.409
_refine_diff_density_min         -0.338
_refine_diff_density_rms         0.085

# start Validation Reply Form
_vrf_PLAT015_shrv406             
;
PROBLEM: No _shelx_hkl_file record in SHELXL20xy CIF ....     Please Do ! 
RESPONSE: It is our policy to routinely not supply the HKL file unless 
specifically required.
;
# end Validation Reply Form
####################################################################### 
# 
# 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_shrv411
_database_code_depnum_ccdc_archive 'CCDC 1480145'
_audit_update_record             
;
2016-05-17 deposited with the CCDC.
2016-08-19 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         '(C4 H3 N11 O4), 2(H5 N2), 0.5(H2O)'
_chemical_formula_sum            'C4 H14 N15 O4.50'
_chemical_formula_weight         344.30

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'
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'
H H 0.0000 0.0000 '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+1/2'
'x+1/2, -y+1/2, z'

_cell_length_a                   16.6803(14)
_cell_length_b                   3.7404(3)
_cell_length_c                   42.897(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2676.4(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    8438
_cell_measurement_theta_min      4.1225
_cell_measurement_theta_max      68.7145

_exptl_crystal_description       needle
_exptl_crystal_colour            'clear white'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.709
_exptl_crystal_F_000             1432
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.160
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    1.295
_shelx_estimated_absorpt_T_min   0.820
_shelx_estimated_absorpt_T_max   0.962
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5874
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_process_details   'SADABS v2014/5 (Bruker, 2008)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_monochromator  'Helios optics'
_diffrn_measurement_device       'Bruker PLATINUM 135 CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12868
_diffrn_reflns_av_unetI/netI     0.0516
_diffrn_reflns_av_R_equivalents  0.0526
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_k_max       3
_diffrn_reflns_limit_l_min       -41
_diffrn_reflns_limit_l_max       48
_diffrn_reflns_theta_min         2.060
_diffrn_reflns_theta_max         68.228
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.957
_diffrn_measured_fraction_theta_full 0.960
_diffrn_reflns_Laue_measured_fraction_max 0.957
_diffrn_reflns_Laue_measured_fraction_full 0.960
_diffrn_reflns_point_group_measured_fraction_max 0.829
_diffrn_reflns_point_group_measured_fraction_full 0.833
_reflns_number_total             4085
_reflns_number_gt                3906
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.707
_reflns_Friedel_fraction_max     0.697
_reflns_Friedel_fraction_full    0.702

_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          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0900P)²+0.8014P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_chemical_absolute_configuration ?
_refine_ls_number_reflns         4085
_refine_ls_number_parameters     458
_refine_ls_number_restraints     16
_refine_ls_R_factor_all          0.0510
_refine_ls_R_factor_gt           0.0493
_refine_ls_wR_factor_ref         0.1299
_refine_ls_wR_factor_gt          0.1281
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_restrained_S_all      1.074
_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 0.66361(19) 0.0509(10) 0.06102(9) 0.0230(8) Uani 1 1 d . . . . .
O2 O 0.69176(18) 0.0335(8) 0.01155(8) 0.0146(7) Uani 1 1 d . . . . .
N3 N 0.7105(2) 0.1188(9) 0.03897(9) 0.0118(8) Uani 1 1 d . . . . .
N4 N 0.7799(2) 0.2789(10) 0.04298(10) 0.0108(8) Uani 1 1 d . . . . .
C5 C 0.7978(2) 0.3861(10) 0.07293(11) 0.0102(9) Uani 1 1 d . . . . .
N6 N 0.7573(2) 0.3509(11) 0.09952(9) 0.0114(8) Uani 1 1 d . . . . .
H6 H 0.7107 0.2427 0.1013 0.014 Uiso 1 1 calc R U . . .
N7 N 0.7982(2) 0.5066(10) 0.12358(9) 0.0128(8) Uani 1 1 d . . . . .
C8 C 0.8629(2) 0.6306(11) 0.10932(11) 0.0098(9) Uani 1 1 d . . . . .
N9 N 0.8663(2) 0.5638(9) 0.07830(10) 0.0121(8) Uani 1 1 d . . . . .
C10 C 0.9246(3) 0.8447(12) 0.12623(12) 0.0123(9) Uani 1 1 d . . . . .
H10A H 0.9407 1.0487 0.1129 0.015 Uiso 1 1 calc R U . . .
H10B H 0.9002 0.9436 0.1454 0.015 Uiso 1 1 calc R U . . .
N11 N 0.9972(2) 0.6418(9) 0.13493(10) 0.0109(8) Uani 1 1 d . . . . .
N12 N 1.0611(2) 0.6286(10) 0.11574(10) 0.0139(8) Uani 1 1 d . . . . .
N13 N 1.1151(2) 0.4509(11) 0.13044(10) 0.0164(8) Uani 1 1 d . . . . .
N14 N 1.0891(2) 0.3438(11) 0.15929(10) 0.0146(8) Uani 1 1 d . . . . .
C15 C 1.0145(3) 0.4686(11) 0.16185(11) 0.0119(9) Uani 1 1 d . . . . .
N16 N 0.9542(2) 0.4516(10) 0.18312(10) 0.0141(8) Uani 1 1 d . . . . .
N17 N 0.9699(2) 0.2754(11) 0.20913(11) 0.0148(9) Uani 1 1 d . . . . .
O18 O 0.9120(2) 0.2662(9) 0.22873(10) 0.0183(9) Uani 1 1 d . . . . .
O19 O 1.0348(2) 0.1341(11) 0.21530(9) 0.0263(9) Uani 1 1 d . . . . .
O20 O 0.40771(19) 0.5531(10) 0.42475(9) 0.0218(8) Uani 1 1 d . . . . .
O21 O 0.43586(19) 0.5384(9) 0.47437(8) 0.0168(7) Uani 1 1 d . . . . .
N22 N 0.4548(2) 0.6237(9) 0.44660(10) 0.0123(8) Uani 1 1 d . . . . .
N23 N 0.5241(2) 0.7838(10) 0.44326(11) 0.0133(8) Uani 1 1 d . . . . .
C24 C 0.5421(2) 0.8923(11) 0.41286(12) 0.0113(9) Uani 1 1 d . . . . .
N25 N 0.5014(2) 0.8527(10) 0.38586(9) 0.0115(8) Uani 1 1 d . . . . .
H25 H 0.4552 0.7415 0.3839 0.014 Uiso 1 1 calc R U . . .
N26 N 0.5421(2) 1.0090(10) 0.36215(10) 0.0136(8) Uani 1 1 d . . . . .
C27 C 0.6063(2) 1.1354(11) 0.37634(11) 0.0100(9) Uani 1 1 d . . . . .
N28 N 0.6098(2) 1.0718(9) 0.40743(10) 0.0121(8) Uani 1 1 d . . . . .
C29 C 0.6684(2) 1.3489(12) 0.35949(11) 0.0120(9) Uani 1 1 d . . . . .
H29A H 0.6440 1.4457 0.3402 0.014 Uiso 1 1 calc R U . . .
H29B H 0.6836 1.5548 0.3727 0.014 Uiso 1 1 calc R U . . .
N30 N 0.7410(2) 1.1555(10) 0.35107(10) 0.0107(8) Uani 1 1 d . . . . .
N31 N 0.8041(2) 1.1349(11) 0.37078(10) 0.0150(9) Uani 1 1 d . . . . .
N32 N 0.8591(2) 0.9619(10) 0.35582(10) 0.0160(9) Uani 1 1 d . . . . .
N33 N 0.8344(2) 0.8638(10) 0.32673(9) 0.0138(8) Uani 1 1 d . . . . .
C34 C 0.7595(3) 0.9865(10) 0.32425(11) 0.0105(9) Uani 1 1 d . . . . .
N35 N 0.7002(2) 0.9716(10) 0.30205(10) 0.0149(9) Uani 1 1 d . . . . .
N36 N 0.7176(2) 0.7989(10) 0.27561(11) 0.0154(9) Uani 1 1 d . . . . .
O37 O 0.6613(2) 0.7841(11) 0.25650(11) 0.0229(9) Uani 1 1 d . . . . .
O38 O 0.78297(19) 0.6600(11) 0.26994(9) 0.0245(8) Uani 1 1 d . . . . .
N39 N 0.7634(2) 0.0468(9) 0.46548(10) 0.0142(8) Uani 1 1 d . . . . .
H39A H 0.8143 0.0483 0.4732 0.021 Uiso 1 1 calc R U . . .
H39B H 0.7524 -0.1723 0.4573 0.021 Uiso 1 1 calc R U . . .
H39C H 0.7282 0.0955 0.4811 0.021 Uiso 1 1 calc R U . . .
N40 N 0.7562(2) 0.3158(10) 0.44135(11) 0.0140(8) Uani 1 1 d D . . . .
H40A H 0.7085(15) 0.282(16) 0.4316(11) 0.021 Uiso 1 1 d D U . . .
H40B H 0.796(2) 0.259(16) 0.4274(10) 0.021 Uiso 1 1 d D U . . .
N41 N 0.7074(2) 0.3394(11) 0.20558(11) 0.0160(9) Uani 1 1 d . . . . .
H41A H 0.7310 0.1206 0.2067 0.024 Uiso 1 1 calc R U . . .
H41B H 0.6650 0.3296 0.1922 0.024 Uiso 1 1 calc R U . . .
H41C H 0.6898 0.4050 0.2248 0.024 Uiso 1 1 calc R U . . .
N42 N 0.7651(2) 0.5999(11) 0.19437(10) 0.0167(8) Uani 1 1 d D . . . .
H42A H 0.775(3) 0.554(16) 0.1738(4) 0.025 Uiso 1 1 d D U . . .
H42B H 0.809(2) 0.529(15) 0.2052(10) 0.025 Uiso 1 1 d D U . . .
N43 N 0.4529(2) 0.7715(10) 0.27994(11) 0.0155(9) Uani 1 1 d . . . . .
H43A H 0.4099 0.7697 0.2929 0.023 Uiso 1 1 calc R U . . .
H43B H 0.4763 0.5516 0.2798 0.023 Uiso 1 1 calc R U . . .
H43C H 0.4366 0.8279 0.2603 0.023 Uiso 1 1 calc R U . . .
N44 N 0.5112(2) 1.0387(12) 0.29078(11) 0.0200(9) Uani 1 1 d D . . . .
H44A H 0.5610(17) 0.985(16) 0.2832(12) 0.030 Uiso 1 1 d D U . . .
H44B H 0.512(3) 0.997(17) 0.3118(4) 0.030 Uiso 1 1 d D U . . .
N45 N 0.0187(2) 0.5497(10) 0.02064(10) 0.0147(8) Uani 1 1 d . . . . .
H45A H 0.0671 0.5696 0.0110 0.022 Uiso 1 1 calc R U . . .
H45B H -0.0212 0.5814 0.0064 0.022 Uiso 1 1 calc R U . . .
H45C H 0.0143 0.3287 0.0293 0.022 Uiso 1 1 calc R U . . .
N46 N 0.0123(2) 0.8181(10) 0.04465(11) 0.0136(8) Uani 1 1 d D . . . .
H46A H 0.0559(19) 0.736(15) 0.0552(11) 0.020 Uiso 1 1 d D U . . .
H46B H -0.0327(18) 0.764(15) 0.0557(11) 0.020 Uiso 1 1 d D U . . .
O47 O 0.6219(2) 0.4055(8) 0.49296(11) 0.0199(6) Uani 1 1 d D . . . .
H47B H 0.604(3) 0.548(13) 0.4801(12) 0.030 Uiso 1 1 d D U . . .
H47A H 0.646(3) 0.528(14) 0.5059(11) 0.030 Uiso 1 1 d D 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 N3 1.254(5) . ?
O2 N3 1.258(5) . ?
N3 N4 1.314(5) . ?
N4 C5 1.378(7) . ?
C5 N6 1.332(6) . ?
C5 N9 1.343(6) . ?
N6 N7 1.368(5) . ?
N6 H6 0.8800 . ?
N7 C8 1.324(6) . ?
C8 N9 1.355(6) . ?
C8 C10 1.493(6) . ?
C10 N11 1.477(6) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
N11 N12 1.347(5) . ?
N11 C15 1.355(7) . ?
N12 N13 1.285(6) . ?
N13 N14 1.371(6) . ?
N14 C15 1.334(6) . ?
C15 N16 1.359(6) . ?
N16 N17 1.322(6) . ?
N17 O19 1.232(5) . ?
N17 O18 1.281(6) . ?
O20 N22 1.251(5) . ?
O21 N22 1.273(5) . ?
N22 N23 1.310(5) . ?
N23 C24 1.398(7) . ?
C24 N28 1.335(6) . ?
C24 N25 1.350(6) . ?
N25 N26 1.355(6) . ?
N25 H25 0.8800 . ?
N26 C27 1.320(6) . ?
C27 N28 1.356(6) . ?
C27 C29 1.494(6) . ?
C29 N30 1.456(6) . ?
C29 H29A 0.9900 . ?
C29 H29B 0.9900 . ?
N30 C34 1.349(6) . ?
N30 N31 1.352(5) . ?
N31 N32 1.294(6) . ?
N32 N33 1.365(6) . ?
N33 C34 1.335(6) . ?
C34 N35 1.374(6) . ?
N35 N36 1.337(6) . ?
N36 O38 1.232(5) . ?
N36 O37 1.248(6) . ?
N39 N40 1.448(6) . ?
N39 H39A 0.9100 . ?
N39 H39B 0.9100 . ?
N39 H39C 0.9100 . ?
N40 H40A 0.908(14) . ?
N40 H40B 0.915(14) . ?
N41 N42 1.452(6) . ?
N41 H41A 0.9100 . ?
N41 H41B 0.9100 . ?
N41 H41C 0.9100 . ?
N42 H42A 0.915(14) . ?
N42 H42B 0.913(14) . ?
N43 N44 1.469(6) . ?
N43 H43A 0.9100 . ?
N43 H43B 0.9100 . ?
N43 H43C 0.9100 . ?
N44 H44A 0.915(14) . ?
N44 H44B 0.914(14) . ?
N45 N46 1.442(6) . ?
N45 H45A 0.9100 . ?
N45 H45B 0.9100 . ?
N45 H45C 0.9100 . ?
N46 H46A 0.909(14) . ?
N46 H46B 0.910(14) . ?
O47 H47B 0.822(14) . ?
O47 H47A 0.823(14) . ?

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 120.0(4) . . ?
O1 N3 N4 122.9(4) . . ?
O2 N3 N4 117.2(4) . . ?
N3 N4 C5 116.5(4) . . ?
N6 C5 N9 109.5(4) . . ?
N6 C5 N4 131.2(4) . . ?
N9 C5 N4 119.2(4) . . ?
C5 N6 N7 110.5(4) . . ?
C5 N6 H6 124.7 . . ?
N7 N6 H6 124.7 . . ?
C8 N7 N6 102.0(4) . . ?
N7 C8 N9 115.1(4) . . ?
N7 C8 C10 121.7(4) . . ?
N9 C8 C10 123.2(4) . . ?
C5 N9 C8 102.9(4) . . ?
N11 C10 C8 114.4(4) . . ?
N11 C10 H10A 108.7 . . ?
C8 C10 H10A 108.7 . . ?
N11 C10 H10B 108.7 . . ?
C8 C10 H10B 108.7 . . ?
H10A C10 H10B 107.6 . . ?
N12 N11 C15 109.6(3) . . ?
N12 N11 C10 120.8(4) . . ?
C15 N11 C10 129.4(4) . . ?
N13 N12 N11 105.9(4) . . ?
N12 N13 N14 111.9(4) . . ?
C15 N14 N13 105.5(4) . . ?
N14 C15 N11 107.2(4) . . ?
N14 C15 N16 136.8(5) . . ?
N11 C15 N16 115.9(4) . . ?
N17 N16 C15 116.3(4) . . ?
O19 N17 O18 120.6(4) . . ?
O19 N17 N16 124.7(4) . . ?
O18 N17 N16 114.7(4) . . ?
O20 N22 O21 119.5(4) . . ?
O20 N22 N23 124.6(4) . . ?
O21 N22 N23 115.8(4) . . ?
N22 N23 C24 115.1(4) . . ?
N28 C24 N25 109.3(4) . . ?
N28 C24 N23 119.4(4) . . ?
N25 C24 N23 131.3(4) . . ?
C24 N25 N26 110.2(3) . . ?
C24 N25 H25 124.9 . . ?
N26 N25 H25 124.9 . . ?
C27 N26 N25 102.3(4) . . ?
N26 C27 N28 115.3(4) . . ?
N26 C27 C29 122.0(4) . . ?
N28 C27 C29 122.6(4) . . ?
C24 N28 C27 102.8(4) . . ?
N30 C29 C27 115.5(4) . . ?
N30 C29 H29A 108.4 . . ?
C27 C29 H29A 108.4 . . ?
N30 C29 H29B 108.4 . . ?
C27 C29 H29B 108.4 . . ?
H29A C29 H29B 107.5 . . ?
C34 N30 N31 109.2(3) . . ?
C34 N30 C29 129.4(4) . . ?
N31 N30 C29 121.4(4) . . ?
N32 N31 N30 105.7(4) . . ?
N31 N32 N33 111.9(4) . . ?
C34 N33 N32 105.3(4) . . ?
N33 C34 N30 107.9(4) . . ?
N33 C34 N35 135.6(4) . . ?
N30 C34 N35 116.4(4) . . ?
N36 N35 C34 116.8(4) . . ?
O38 N36 O37 121.2(5) . . ?
O38 N36 N35 124.3(4) . . ?
O37 N36 N35 114.5(4) . . ?
N40 N39 H39A 109.5 . . ?
N40 N39 H39B 109.5 . . ?
H39A N39 H39B 109.5 . . ?
N40 N39 H39C 109.5 . . ?
H39A N39 H39C 109.5 . . ?
H39B N39 H39C 109.5 . . ?
N39 N40 H40A 108(4) . . ?
N39 N40 H40B 104(4) . . ?
H40A N40 H40B 107(3) . . ?
N42 N41 H41A 109.5 . . ?
N42 N41 H41B 109.5 . . ?
H41A N41 H41B 109.5 . . ?
N42 N41 H41C 109.5 . . ?
H41A N41 H41C 109.5 . . ?
H41B N41 H41C 109.5 . . ?
N41 N42 H42A 108(4) . . ?
N41 N42 H42B 100(4) . . ?
H42A N42 H42B 107(3) . . ?
N44 N43 H43A 109.5 . . ?
N44 N43 H43B 109.5 . . ?
H43A N43 H43B 109.5 . . ?
N44 N43 H43C 109.5 . . ?
H43A N43 H43C 109.5 . . ?
H43B N43 H43C 109.5 . . ?
N43 N44 H44A 110(4) . . ?
N43 N44 H44B 102(4) . . ?
H44A N44 H44B 108(3) . . ?
N46 N45 H45A 109.5 . . ?
N46 N45 H45B 109.5 . . ?
H45A N45 H45B 109.5 . . ?
N46 N45 H45C 109.5 . . ?
H45A N45 H45C 109.5 . . ?
H45B N45 H45C 109.5 . . ?
N45 N46 H46A 94(4) . . ?
N45 N46 H46B 106(4) . . ?
H46A N46 H46B 109(3) . . ?
H47B O47 H47A 105(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 N3 N4 C5 -2.9(6) . . . . ?
O2 N3 N4 C5 177.0(3) . . . . ?
N3 N4 C5 N6 1.4(7) . . . . ?
N3 N4 C5 N9 -177.4(3) . . . . ?
N9 C5 N6 N7 0.1(5) . . . . ?
N4 C5 N6 N7 -178.8(4) . . . . ?
C5 N6 N7 C8 0.2(4) . . . . ?
N6 N7 C8 N9 -0.4(4) . . . . ?
N6 N7 C8 C10 176.4(4) . . . . ?
N6 C5 N9 C8 -0.3(4) . . . . ?
N4 C5 N9 C8 178.7(4) . . . . ?
N7 C8 N9 C5 0.5(5) . . . . ?
C10 C8 N9 C5 -176.3(4) . . . . ?
N7 C8 C10 N11 101.5(5) . . . . ?
N9 C8 C10 N11 -81.9(5) . . . . ?
C8 C10 N11 N12 91.3(5) . . . . ?
C8 C10 N11 C15 -93.5(6) . . . . ?
C15 N11 N12 N13 0.5(5) . . . . ?
C10 N11 N12 N13 176.6(4) . . . . ?
N11 N12 N13 N14 -0.2(5) . . . . ?
N12 N13 N14 C15 -0.2(5) . . . . ?
N13 N14 C15 N11 0.5(5) . . . . ?
N13 N14 C15 N16 177.2(5) . . . . ?
N12 N11 C15 N14 -0.7(5) . . . . ?
C10 N11 C15 N14 -176.3(4) . . . . ?
N12 N11 C15 N16 -178.1(4) . . . . ?
C10 N11 C15 N16 6.2(6) . . . . ?
N14 C15 N16 N17 2.0(8) . . . . ?
N11 C15 N16 N17 178.4(4) . . . . ?
C15 N16 N17 O19 1.2(7) . . . . ?
C15 N16 N17 O18 179.6(4) . . . . ?
O20 N22 N23 C24 3.0(6) . . . . ?
O21 N22 N23 C24 -176.8(3) . . . . ?
N22 N23 C24 N28 177.1(3) . . . . ?
N22 N23 C24 N25 -2.1(6) . . . . ?
N28 C24 N25 N26 -0.4(5) . . . . ?
N23 C24 N25 N26 178.8(4) . . . . ?
C24 N25 N26 C27 0.2(4) . . . . ?
N25 N26 C27 N28 0.0(5) . . . . ?
N25 N26 C27 C29 -177.1(4) . . . . ?
N25 C24 N28 C27 0.3(4) . . . . ?
N23 C24 N28 C27 -179.0(4) . . . . ?
N26 C27 N28 C24 -0.2(5) . . . . ?
C29 C27 N28 C24 176.9(4) . . . . ?
N26 C27 C29 N30 -101.6(5) . . . . ?
N28 C27 C29 N30 81.5(5) . . . . ?
C27 C29 N30 C34 93.9(5) . . . . ?
C27 C29 N30 N31 -88.7(5) . . . . ?
C34 N30 N31 N32 0.8(4) . . . . ?
C29 N30 N31 N32 -177.1(4) . . . . ?
N30 N31 N32 N33 -0.5(5) . . . . ?
N31 N32 N33 C34 -0.1(5) . . . . ?
N32 N33 C34 N30 0.6(5) . . . . ?
N32 N33 C34 N35 -177.5(5) . . . . ?
N31 N30 C34 N33 -0.9(5) . . . . ?
C29 N30 C34 N33 176.8(4) . . . . ?
N31 N30 C34 N35 177.6(4) . . . . ?
C29 N30 C34 N35 -4.7(6) . . . . ?
N33 C34 N35 N36 -0.8(7) . . . . ?
N30 C34 N35 N36 -178.8(4) . . . . ?
C34 N35 N36 O38 -1.2(6) . . . . ?
C34 N35 N36 O37 178.2(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 H6 O1 0.88 2.03 2.535(5) 115.3 .
N6 H6 N13 0.88 2.15 2.943(5) 149.5 4_455
N25 H25 O20 0.88 2.05 2.546(5) 115.0 .
N25 H25 N32 0.88 2.15 2.946(5) 151.0 4_465
N39 H39A O21 0.91 2.05 2.919(5) 158.0 4
N39 H39A N22 0.91 2.69 3.354(5) 131.1 4
N39 H39C O47 0.91 2.18 2.960(5) 143.6 .
N40 H40A N28 0.908(14) 2.10(2) 2.985(6) 165(5) 1_545
N40 H40B O20 0.915(14) 2.21(4) 2.966(5) 140(5) 4
N40 H40B N31 0.915(14) 2.47(4) 3.203(6) 137(4) 1_545
N41 H41B N14 0.91 2.00 2.881(6) 161.2 4_455
N41 H41B O19 0.91 2.39 2.911(5) 116.2 4_455
N41 H41C N36 0.91 2.67 3.465(6) 146.4 .
N41 H41C O37 0.91 2.02 2.851(7) 151.1 .
N41 H41C O38 0.91 2.66 3.263(6) 124.7 .
N42 H42A N7 0.915(14) 2.195(16) 3.106(6) 174(5) .
N42 H42B N16 0.913(14) 2.61(5) 3.238(5) 127(4) .
N42 H42B O18 0.913(14) 2.216(18) 3.120(6) 170(5) .
N43 H43A N33 0.91 1.98 2.863(6) 162.1 4_465
N43 H43A O38 0.91 2.35 2.879(5) 116.9 4_465
N43 H43C O18 0.91 2.08 2.878(6) 146.4 4_465
N44 H44A N35 0.915(14) 2.46(4) 3.199(5) 138(4) .
N44 H44A O37 0.915(14) 2.16(2) 3.055(6) 165(5) .
N44 H44B N26 0.914(14) 2.22(2) 3.107(6) 164(5) .
N45 H45A O2 0.91 2.12 2.929(5) 148.4 4_455
N45 H45A O21 0.91 2.35 2.803(5) 110.2 3_554
N45 H45B O47 0.91 2.15 2.947(6) 145.6 3_554
N46 H46A O1 0.909(14) 2.11(3) 2.961(5) 156(5) 4_455
N46 H46A N12 0.909(14) 2.63(4) 3.235(6) 125(4) 1_455
N46 H46B N9 0.910(14) 2.083(17) 2.986(6) 172(5) 1_455
O47 H47B N23 0.822(14) 2.25(2) 3.035(6) 160(6) .
O47 H47A N4 0.823(14) 2.225(17) 3.039(6) 171(6) 3_655

_refine_diff_density_max         0.545
_refine_diff_density_min         -0.348
_refine_diff_density_rms         0.082

# start Validation Reply Form
_vrf_PLAT015_shrv411             
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PROBLEM: No _shelx_hkl_file record in SHELXL20xy CIF ....     Please Do ! 
RESPONSE: It is our policy to routinely not supply the HKL files unless specifically required.
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# end Validation Reply Form
