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

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

data_1
_database_code_depnum_ccdc_archive 'CCDC 1816899'
_audit_update_record             
;
2018-01-15 deposited with the CCDC.
2018-06-29 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         'C8 H2 N12 O8, 2(H2 O)'
_chemical_formula_sum            'C8 H6 N12 O10'
_chemical_formula_weight         430.25

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

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

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

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

_cell_length_a                   4.5145(4)
_cell_length_b                   12.0237(11)
_cell_length_c                   28.870(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1567.1(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    1487
_cell_measurement_theta_min      2.82
_cell_measurement_theta_max      25.13

_exptl_crystal_description       sheet
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.824
_exptl_crystal_F_000             872
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    0.167
_shelx_estimated_absorpt_T_min   0.944
_shelx_estimated_absorpt_T_max   0.995
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6613
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_process_details   'SADABS (Bruker, 2014)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'PHOTON 100 CMOS detector'
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6759
_diffrn_reflns_av_unetI/netI     0.0468
_diffrn_reflns_av_R_equivalents  0.0736
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_theta_min         2.822
_diffrn_reflns_theta_max         25.321
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             1436
_reflns_number_gt                1037
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0460P)²+0.5037P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1436
_refine_ls_number_parameters     145
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0733
_refine_ls_R_factor_gt           0.0431
_refine_ls_wR_factor_ref         0.0991
_refine_ls_wR_factor_gt          0.0876
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_restrained_S_all      1.040
_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
C1 C 0.0428(6) 0.82885(19) 0.43596(8) 0.0136(5) Uani 1 1 d . . . . .
C2 C 0.0302(5) 0.95867(19) 0.48212(8) 0.0146(5) Uani 1 1 d . . . . .
C3 C 0.0855(5) 0.68447(19) 0.36857(8) 0.0140(5) Uani 1 1 d . . . . .
C4 C -0.0318(5) 0.72717(19) 0.41113(8) 0.0135(5) Uani 1 1 d . . . . .
N1 N 0.2695(5) 0.88908(17) 0.42327(7) 0.0204(5) Uani 1 1 d . . . . .
N2 N -0.1148(5) 0.86887(16) 0.47327(6) 0.0150(5) Uani 1 1 d . . . . .
N3 N -0.0400(5) 0.58958(16) 0.35925(7) 0.0188(5) Uani 1 1 d . . . . .
N4 N -0.2311(5) 0.65841(16) 0.42623(7) 0.0187(5) Uani 1 1 d . . . . .
N5 N 0.3125(5) 0.72572(17) 0.34054(7) 0.0188(5) Uani 1 1 d . . . . .
H5 H 0.401(6) 0.678(2) 0.3207(9) 0.023 Uiso 1 1 d . U . . .
N6 N 0.2527(5) 0.82447(18) 0.31734(7) 0.0204(5) Uani 1 1 d . . . . .
O1 O 0.2632(4) 0.97835(13) 0.45459(6) 0.0192(4) Uani 1 1 d . . . . .
O2 O -0.2366(4) 0.57158(13) 0.39478(6) 0.0211(4) Uani 1 1 d . . . . .
O3 O 0.0372(4) 0.87816(15) 0.32999(6) 0.0250(5) Uani 1 1 d . . . . .
O4 O 0.4268(4) 0.84942(16) 0.28713(6) 0.0306(5) Uani 1 1 d . . . . .
O5 O 0.5078(4) 0.57612(14) 0.27661(6) 0.0188(4) Uani 1 1 d D . . . .
H5A H 0.496(6) 0.5171(16) 0.2912(8) 0.023 Uiso 1 1 d D U . . .
H5B H 0.662(5) 0.576(2) 0.2613(8) 0.023 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
C1 N1 1.306(3) . ?
C1 N2 1.377(3) . ?
C1 C4 1.457(3) . ?
C2 N2 1.288(3) . ?
C2 O1 1.340(3) . ?
C2 C2 1.459(4) 5_576 ?
C3 N3 1.302(3) . ?
C3 N5 1.397(3) . ?
C3 C4 1.433(3) . ?
C4 N4 1.298(3) . ?
N1 O1 1.404(2) . ?
N3 O2 1.373(3) . ?
N4 O2 1.384(2) . ?
N5 N6 1.390(3) . ?
N5 H5 0.91(3) . ?
N6 O4 1.212(3) . ?
N6 O3 1.223(3) . ?
O5 H5A 0.826(16) . ?
O5 H5B 0.823(17) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 N2 115.5(2) . . ?
N1 C1 C4 120.6(2) . . ?
N2 C1 C4 124.0(2) . . ?
N2 C2 O1 115.4(2) . . ?
N2 C2 C2 128.1(3) . 5_576 ?
O1 C2 C2 116.5(3) . 5_576 ?
N3 C3 N5 120.7(2) . . ?
N3 C3 C4 109.3(2) . . ?
N5 C3 C4 129.8(2) . . ?
N4 C4 C3 108.4(2) . . ?
N4 C4 C1 122.0(2) . . ?
C3 C4 C1 129.6(2) . . ?
C1 N1 O1 103.16(18) . . ?
C2 N2 C1 100.7(2) . . ?
C3 N3 O2 105.37(18) . . ?
C4 N4 O2 105.81(19) . . ?
N6 N5 C3 116.1(2) . . ?
N6 N5 H5 109.1(16) . . ?
C3 N5 H5 117.5(17) . . ?
O4 N6 O3 126.9(2) . . ?
O4 N6 N5 115.6(2) . . ?
O3 N6 N5 117.5(2) . . ?
C2 O1 N1 105.24(17) . . ?
N3 O2 N4 111.07(16) . . ?
H5A O5 H5B 109(3) . . ?

_refine_diff_density_max         0.258
_refine_diff_density_min         -0.268
_refine_diff_density_rms         0.061

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

data_1_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1816905'
_audit_update_record             
;
2018-01-15 deposited with the CCDC.
2018-06-29 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         'C8 K2 N12 O8'
_chemical_formula_sum            'C8 K2 N12 O8'
_chemical_formula_weight         470.40

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
K K 0.2009 0.2494 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   4.7645(6)
_cell_length_b                   6.9326(8)
_cell_length_c                   12.4985(14)
_cell_angle_alpha                100.528(4)
_cell_angle_beta                 93.057(4)
_cell_angle_gamma                108.417(4)
_cell_volume                     382.35(8)
_cell_formula_units_Z            1
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    957
_cell_measurement_theta_min      3.17
_cell_measurement_theta_max      25.29

_exptl_crystal_description       needle
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.043
_exptl_crystal_F_000             234
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    0.703
_shelx_estimated_absorpt_T_min   0.902
_shelx_estimated_absorpt_T_max   0.966
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6620
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_process_details   'SADABS (Bruker, 2014)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'PHOTON 100 CMOS detector'
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            3442
_diffrn_reflns_av_unetI/netI     0.0736
_diffrn_reflns_av_R_equivalents  0.0624
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.168
_diffrn_reflns_theta_max         25.349
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measured_fraction_theta_full 0.977
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_Laue_measured_fraction_full 0.977
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_point_group_measured_fraction_full 0.977
_reflns_number_total             1381
_reflns_number_gt                974
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0188P)²+0.2866P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   .
_refine_ls_hydrogen_treatment    undef
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1381
_refine_ls_number_parameters     136
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0783
_refine_ls_R_factor_gt           0.0419
_refine_ls_wR_factor_ref         0.0791
_refine_ls_wR_factor_gt          0.0696
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_restrained_S_all      1.047
_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
C1 C 0.7356(7) 0.3073(5) 0.6407(3) 0.0142(8) Uani 1 1 d . . . . .
C2 C 0.5808(8) 0.4628(5) 0.5387(3) 0.0153(8) Uani 1 1 d . . . . .
C3 C 0.9723(7) 0.1371(5) 0.7772(3) 0.0121(7) Uani 1 1 d . . . . .
C4 C 0.7472(8) 0.1420(5) 0.6965(3) 0.0139(7) Uani 1 1 d . . . . .
K1 K 1.18596(18) 0.71288(12) 0.89306(6) 0.0189(2) Uani 1 1 d . . . . .
N1 N 0.9498(6) 0.4873(4) 0.6576(2) 0.0186(7) Uani 1 1 d . . . . .
N2 N 0.4963(6) 0.2851(4) 0.5666(2) 0.0174(7) Uani 1 1 d . . . . .
N3 N 0.8816(6) -0.0446(4) 0.8055(2) 0.0178(7) Uani 1 1 d . . . . .
N4 N 0.5231(6) -0.0317(4) 0.6781(2) 0.0181(7) Uani 1 1 d . . . . .
N5 N 1.2285(6) 0.3062(4) 0.8106(2) 0.0143(7) Uani 1 1 d . . . . .
N6 N 1.4207(6) 0.2892(4) 0.8854(2) 0.0142(6) Uani 1 1 d . . . . .
O1 O 0.8462(5) 0.5951(3) 0.58769(18) 0.0197(6) Uani 1 1 d . . . . .
O2 O 0.6010(5) -0.1508(3) 0.74338(19) 0.0208(6) Uani 1 1 d . . . . .
O3 O 1.3774(6) 0.1356(4) 0.92895(19) 0.0251(6) Uani 1 1 d . . . . .
O4 O 1.6622(5) 0.4405(3) 0.91217(18) 0.0189(6) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.311(4) . ?
C1 N2 1.380(4) . ?
C1 C4 1.459(5) . ?
C2 N2 1.289(4) . ?
C2 O1 1.340(4) . ?
C2 C2 1.465(6) 2_666 ?
C3 N3 1.317(4) . ?
C3 N5 1.378(4) . ?
C3 C4 1.445(4) . ?
C4 N4 1.305(4) . ?
K1 O4 2.665(3) 1_455 ?
K1 O3 2.722(2) 1_565 ?
K1 O3 2.766(2) 2_867 ?
K1 N3 2.858(3) 1_565 ?
K1 O2 2.857(3) 1_665 ?
K1 N5 2.894(3) . ?
K1 O4 2.970(2) 2_867 ?
K1 N1 3.037(3) . ?
K1 N6 3.265(3) 2_867 ?
K1 O4 3.404(3) . ?
K1 N6 3.445(3) . ?
K1 K1 4.3682(17) 2_767 ?
N1 O1 1.412(3) . ?
N3 O2 1.411(3) . ?
N3 K1 2.859(3) 1_545 ?
N4 O2 1.376(3) . ?
N5 N6 1.321(4) . ?
N6 O3 1.248(3) . ?
N6 O4 1.266(3) . ?
N6 K1 3.265(3) 2_867 ?
O2 K1 2.857(3) 1_445 ?
O3 K1 2.722(2) 1_545 ?
O3 K1 2.766(2) 2_867 ?
O4 K1 2.665(3) 1_655 ?
O4 K1 2.970(2) 2_867 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 N2 115.2(3) . . ?
N1 C1 C4 122.6(3) . . ?
N2 C1 C4 122.2(3) . . ?
N2 C2 O1 115.6(3) . . ?
N2 C2 C2 127.7(4) . 2_666 ?
O1 C2 C2 116.7(4) . 2_666 ?
N3 C3 N5 131.5(3) . . ?
N3 C3 C4 108.2(3) . . ?
N5 C3 C4 120.2(3) . . ?
N4 C4 C3 110.1(3) . . ?
N4 C4 C1 119.6(3) . . ?
C3 C4 C1 130.3(3) . . ?
O4 K1 O3 131.16(8) 1_455 1_565 ?
O4 K1 O3 119.08(8) 1_455 2_867 ?
O3 K1 O3 72.14(8) 1_565 2_867 ?
O4 K1 N3 89.51(8) 1_455 1_565 ?
O3 K1 N3 54.59(7) 1_565 1_565 ?
O3 K1 N3 124.59(8) 2_867 1_565 ?
O4 K1 O2 144.55(7) 1_455 1_665 ?
O3 K1 O2 70.47(8) 1_565 1_665 ?
O3 K1 O2 92.80(8) 2_867 1_665 ?
N3 K1 O2 83.77(8) 1_565 1_665 ?
O4 K1 N5 74.21(8) 1_455 . ?
O3 K1 N5 154.13(9) 1_565 . ?
O3 K1 N5 101.63(7) 2_867 . ?
N3 K1 N5 132.80(8) 1_565 . ?
O2 K1 N5 85.09(8) 1_665 . ?
O4 K1 O4 78.50(7) 1_455 2_867 ?
O3 K1 O4 112.39(7) 1_565 2_867 ?
O3 K1 O4 44.39(7) 2_867 2_867 ?
N3 K1 O4 146.77(8) 1_565 2_867 ?
O2 K1 O4 123.21(7) 1_665 2_867 ?
N5 K1 O4 73.69(7) . 2_867 ?
O4 K1 N1 76.94(8) 1_455 . ?
O3 K1 N1 115.53(8) 1_565 . ?
O3 K1 N1 152.73(9) 2_867 . ?
N3 K1 N1 73.94(8) 1_565 . ?
O2 K1 N1 67.74(8) 1_665 . ?
N5 K1 N1 59.41(7) . . ?
O4 K1 N1 131.27(7) 2_867 . ?
O4 K1 N6 100.47(8) 1_455 2_867 ?
O3 K1 N6 93.11(7) 1_565 2_867 ?
O3 K1 N6 21.94(7) 2_867 2_867 ?
N3 K1 N6 141.51(8) 1_565 2_867 ?
O2 K1 N6 106.36(7) 1_665 2_867 ?
N5 K1 N6 85.55(7) . 2_867 ?
O4 K1 N6 22.81(6) 2_867 2_867 ?
N1 K1 N6 144.47(7) . 2_867 ?
O4 K1 O4 102.78(7) 1_455 . ?
O3 K1 O4 122.32(7) 1_565 . ?
O3 K1 O4 63.63(6) 2_867 . ?
N3 K1 O4 159.23(8) 1_565 . ?
O2 K1 O4 76.50(7) 1_665 . ?
N5 K1 O4 39.78(6) . . ?
O4 K1 O4 53.55(8) 2_867 . ?
N1 K1 O4 92.37(7) . . ?
N6 K1 O4 53.14(6) 2_867 . ?
O4 K1 N6 82.79(7) 1_455 . ?
O3 K1 N6 143.61(8) 1_565 . ?
O3 K1 N6 79.86(7) 2_867 . ?
N3 K1 N6 154.57(8) 1_565 . ?
O2 K1 N6 88.55(7) 1_665 . ?
N5 K1 N6 21.90(6) . . ?
O4 K1 N6 54.85(6) 2_867 . ?
N1 K1 N6 80.71(7) . . ?
N6 K1 N6 63.91(8) 2_867 . ?
O4 K1 N6 21.30(6) . . ?
O4 K1 K1 41.79(5) 1_455 2_767 ?
O3 K1 K1 131.34(6) 1_565 2_767 ?
O3 K1 K1 79.08(6) 2_867 2_767 ?
N3 K1 K1 124.31(7) 1_565 2_767 ?
O2 K1 K1 150.40(6) 1_665 2_767 ?
N5 K1 K1 69.08(6) . 2_767 ?
O4 K1 K1 36.71(5) 2_867 2_767 ?
N1 K1 K1 108.10(6) . 2_767 ?
N6 K1 K1 58.94(5) 2_867 2_767 ?
O4 K1 K1 74.39(5) . 2_767 ?
N6 K1 K1 62.09(5) . 2_767 ?
C1 N1 O1 103.2(2) . . ?
C1 N1 K1 118.0(2) . . ?
O1 N1 K1 117.83(18) . . ?
C2 N2 C1 100.9(3) . . ?
C3 N3 O2 104.8(2) . . ?
C3 N3 K1 133.4(2) . 1_545 ?
O2 N3 K1 117.74(17) . 1_545 ?
C4 N4 O2 105.1(3) . . ?
N6 N5 C3 116.2(3) . . ?
N6 N5 K1 103.26(18) . . ?
C3 N5 K1 119.7(2) . . ?
O3 N6 O4 119.8(3) . . ?
O3 N6 N5 124.1(3) . . ?
O4 N6 N5 116.1(3) . . ?
O3 N6 K1 55.93(15) . 2_867 ?
O4 N6 K1 65.43(15) . 2_867 ?
N5 N6 K1 167.8(2) . 2_867 ?
O3 N6 K1 139.5(2) . . ?
O4 N6 K1 77.49(16) . . ?
N5 N6 K1 54.84(15) . . ?
K1 N6 K1 116.09(8) 2_867 . ?
C2 O1 N1 105.1(2) . . ?
N4 O2 N3 111.7(2) . . ?
N4 O2 K1 114.68(18) . 1_445 ?
N3 O2 K1 107.28(17) . 1_445 ?
N6 O3 K1 145.3(2) . 1_545 ?
N6 O3 K1 102.12(18) . 2_867 ?
K1 O3 K1 107.86(8) 1_545 2_867 ?
N6 O4 K1 159.4(2) . 1_655 ?
N6 O4 K1 91.76(17) . 2_867 ?
K1 O4 K1 101.50(7) 1_655 2_867 ?
N6 O4 K1 81.21(16) . . ?
K1 O4 K1 102.78(7) 1_655 . ?
K1 O4 K1 126.45(8) 2_867 . ?

_refine_diff_density_max         0.362
_refine_diff_density_min         -0.410
_refine_diff_density_rms         0.092

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

data_1_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 1816902'
_audit_update_record             
;
2018-01-15 deposited with the CCDC.
2018-06-29 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(C2 H5 N4), C8 N12 O8'
_chemical_formula_sum            'C12 H10 N20 O8'
_chemical_formula_weight         562.40

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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                   8.0468(5)
_cell_length_b                   16.0227(10)
_cell_length_c                   8.3828(4)
_cell_angle_alpha                90
_cell_angle_beta                 105.085(2)
_cell_angle_gamma                90
_cell_volume                     1043.56(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    2593
_cell_measurement_theta_min      2.91
_cell_measurement_theta_max      25.34

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.790
_exptl_crystal_F_000             572
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.170
_exptl_absorpt_coefficient_mu    0.153
_shelx_estimated_absorpt_T_min   0.970
_shelx_estimated_absorpt_T_max   0.975
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6927
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_process_details   'SADABS (Bruker, 2014)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'PHOTON 100 CMOS detector'
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7276
_diffrn_reflns_av_unetI/netI     0.0326
_diffrn_reflns_av_R_equivalents  0.0425
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         3.375
_diffrn_reflns_theta_max         25.347
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measured_fraction_theta_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_point_group_measured_fraction_full 0.987
_reflns_number_total             1882
_reflns_number_gt                1487
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0375P)²+0.4572P] 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         1882
_refine_ls_number_parameters     190
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0558
_refine_ls_R_factor_gt           0.0369
_refine_ls_wR_factor_ref         0.0837
_refine_ls_wR_factor_gt          0.0766
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_restrained_S_all      1.026
_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
C1 C 0.6898(2) 0.07154(11) 0.0152(2) 0.0149(4) Uani 1 1 d . . . . .
C2 C 0.9217(2) 0.01662(11) 0.0158(2) 0.0159(4) Uani 1 1 d . . . . .
C3 C 0.4024(2) 0.13720(11) 0.0480(2) 0.0159(4) Uani 1 1 d . . . . .
C4 C 0.5255(2) 0.11494(11) -0.0424(2) 0.0161(4) Uani 1 1 d . . . . .
C5 C 0.7447(3) 0.31036(13) 0.0390(3) 0.0292(5) Uani 1 1 d . . . . .
H5 H 0.6331 0.3067 0.0569 0.035 Uiso 1 1 calc R U . . .
C6 C 0.9777(2) 0.36337(12) -0.0018(2) 0.0197(4) Uani 1 1 d . . . . .
H6 H 1.0633 0.4010 -0.0174 0.024 Uiso 1 1 calc R U . . .
N1 N 0.7454(2) 0.04522(10) 0.16673(19) 0.0203(4) Uani 1 1 d . . . . .
N2 N 0.79606(19) 0.05428(9) -0.08603(18) 0.0169(4) Uani 1 1 d . . . . .
N3 N 0.2695(2) 0.17273(10) -0.05607(19) 0.0220(4) Uani 1 1 d . . . . .
N4 N 0.4698(2) 0.13762(11) -0.19590(19) 0.0238(4) Uani 1 1 d . . . . .
N5 N 0.4401(2) 0.12301(10) 0.21511(18) 0.0188(4) Uani 1 1 d . . . . .
N6 N 0.3111(2) 0.13626(9) 0.28501(19) 0.0186(4) Uani 1 1 d . . . . .
N7 N 0.9852(2) 0.28217(11) -0.0009(2) 0.0248(4) Uani 1 1 d D . . . .
H7A H 1.066(2) 0.2513(13) -0.009(3) 0.030 Uiso 1 1 d D U . . .
N8 N 0.8399(2) 0.24662(11) 0.0261(2) 0.0360(5) Uani 1 1 d . . . . .
N9 N 0.8260(2) 0.38307(9) 0.02359(18) 0.0175(4) Uani 1 1 d . . . . .
N10 N 0.7665(2) 0.46563(10) 0.0268(2) 0.0227(4) Uani 1 1 d . . . . .
H10A H 0.725(3) 0.4720(13) 0.114(3) 0.027 Uiso 1 1 d . U . . .
H10B H 0.676(3) 0.4715(13) -0.061(3) 0.027 Uiso 1 1 d . U . . .
O1 O 0.90431(16) 0.00755(8) 0.16905(15) 0.0199(3) Uani 1 1 d . . . . .
O2 O 0.31227(18) 0.17352(9) -0.20884(16) 0.0277(4) Uani 1 1 d . . . . .
O3 O 0.35005(18) 0.13155(9) 0.43921(16) 0.0266(3) Uani 1 1 d . . . . .
O4 O 0.16009(17) 0.15041(9) 0.20376(16) 0.0240(3) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.302(2) . ?
C1 N2 1.381(2) . ?
C1 C4 1.460(3) . ?
C2 N2 1.291(2) . ?
C2 O1 1.336(2) . ?
C2 C2 1.454(4) 3_755 ?
C3 N3 1.320(2) . ?
C3 N5 1.373(2) . ?
C3 C4 1.440(2) . ?
C4 N4 1.299(2) . ?
C5 N8 1.298(3) . ?
C5 N9 1.359(3) . ?
C5 H5 0.9500 . ?
C6 N7 1.302(3) . ?
C6 N9 1.330(2) . ?
C6 H6 0.9500 . ?
N1 O1 1.4093(19) . ?
N3 O2 1.410(2) . ?
N4 O2 1.371(2) . ?
N5 N6 1.336(2) . ?
N6 O4 1.249(2) . ?
N6 O3 1.251(2) . ?
N7 N8 1.371(2) . ?
N7 H7A 0.831(16) . ?
N9 N10 1.409(2) . ?
N10 H10A 0.89(2) . ?
N10 H10B 0.89(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 N2 115.08(16) . . ?
N1 C1 C4 121.93(16) . . ?
N2 C1 C4 122.99(15) . . ?
N2 C2 O1 115.27(16) . . ?
N2 C2 C2 128.1(2) . 3_755 ?
O1 C2 C2 116.6(2) . 3_755 ?
N3 C3 N5 132.20(17) . . ?
N3 C3 C4 107.98(16) . . ?
N5 C3 C4 119.75(16) . . ?
N4 C4 C3 110.16(16) . . ?
N4 C4 C1 120.66(16) . . ?
C3 C4 C1 129.15(16) . . ?
N8 C5 N9 110.96(18) . . ?
N8 C5 H5 124.5 . . ?
N9 C5 H5 124.5 . . ?
N7 C6 N9 106.22(17) . . ?
N7 C6 H6 126.9 . . ?
N9 C6 H6 126.9 . . ?
C1 N1 O1 103.45(13) . . ?
C2 N2 C1 101.01(15) . . ?
C3 N3 O2 104.89(14) . . ?
C4 N4 O2 105.62(14) . . ?
N6 N5 C3 115.50(15) . . ?
O4 N6 O3 121.42(15) . . ?
O4 N6 N5 123.14(15) . . ?
O3 N6 N5 115.43(15) . . ?
C6 N7 N8 112.06(17) . . ?
C6 N7 H7A 129.0(16) . . ?
N8 N7 H7A 118.9(16) . . ?
C5 N8 N7 103.53(17) . . ?
C6 N9 C5 107.23(16) . . ?
C6 N9 N10 123.78(16) . . ?
C5 N9 N10 128.96(16) . . ?
N9 N10 H10A 109.0(14) . . ?
N9 N10 H10B 106.9(14) . . ?
H10A N10 H10B 105(2) . . ?
C2 O1 N1 105.18(13) . . ?
N4 O2 N3 111.33(13) . . ?

_refine_diff_density_max         0.180
_refine_diff_density_min         -0.279
_refine_diff_density_rms         0.063

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

data_1_CCDC3
_database_code_depnum_ccdc_archive 'CCDC 1816903'
_audit_update_record             
;
2018-01-15 deposited with the CCDC.
2018-06-29 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(C2 H5 N4), C8 N12 O8'
_chemical_formula_sum            'C12 H10 N20 O8'
_chemical_formula_weight         562.40

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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                   11.9711(12)
_cell_length_b                   6.8493(6)
_cell_length_c                   13.2618(12)
_cell_angle_alpha                90
_cell_angle_beta                 102.882(3)
_cell_angle_gamma                90
_cell_volume                     1060.02(17)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    1550
_cell_measurement_theta_min      3.15
_cell_measurement_theta_max      25.27

_exptl_crystal_description       plate
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.762
_exptl_crystal_F_000             572
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    0.150
_shelx_estimated_absorpt_T_min   0.968
_shelx_estimated_absorpt_T_max   0.988
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6092
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_process_details   'SADABS (Bruker, 2014)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'PHOTON 100 CMOS detector'
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5970
_diffrn_reflns_av_unetI/netI     0.0629
_diffrn_reflns_av_R_equivalents  0.0652
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.151
_diffrn_reflns_theta_max         25.354
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             1920
_reflns_number_gt                1301
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0343P)²+0.2706P] 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         1920
_refine_ls_number_parameters     193
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0864
_refine_ls_R_factor_gt           0.0453
_refine_ls_wR_factor_ref         0.0942
_refine_ls_wR_factor_gt          0.0820
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.048
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.3839(2) 0.4838(4) 0.79361(17) 0.0172(6) Uani 1 1 d . . . . .
C2 C 0.4627(2) 0.4909(3) 0.94832(18) 0.0192(6) Uani 1 1 d . . . . .
C3 C 0.2704(2) 0.4656(4) 0.59873(18) 0.0174(6) Uani 1 1 d . . . . .
C4 C 0.3671(2) 0.5089(3) 0.68112(19) 0.0178(6) Uani 1 1 d . . . . .
C5 C -0.0876(2) 0.0689(4) 0.28382(19) 0.0245(6) Uani 1 1 d . . . . .
C6 C -0.2722(3) 0.0396(4) 0.2582(2) 0.0361(7) Uani 1 1 d . . . . .
H6 H -0.3493 0.0142 0.2238 0.043 Uiso 1 1 calc R U . . .
N1 N 0.30781(18) 0.4016(3) 0.83666(15) 0.0276(6) Uani 1 1 d . . . . .
N2 N 0.48284(16) 0.5447(3) 0.86095(14) 0.0195(5) Uani 1 1 d . . . . .
N3 N 0.29648(17) 0.5163(3) 0.51130(15) 0.0226(5) Uani 1 1 d . . . . .
N4 N 0.44939(17) 0.5834(3) 0.64385(15) 0.0239(5) Uani 1 1 d . . . . .
N5 N 0.16939(17) 0.3965(3) 0.61776(14) 0.0207(5) Uani 1 1 d . . . . .
N6 N 0.09483(18) 0.3290(3) 0.53750(15) 0.0216(5) Uani 1 1 d . . . . .
N7 N -0.24130(18) 0.0903(3) 0.35421(18) 0.0327(6) Uani 1 1 d . . . . .
N8 N -0.12386(17) 0.1093(3) 0.36906(16) 0.0222(5) Uani 1 1 d . . . . .
H8A H -0.080(2) 0.154(4) 0.4298(19) 0.027 Uiso 1 1 d . U . . .
N9 N -0.1819(2) 0.0265(4) 0.21201(18) 0.0334(6) Uani 1 1 d . . . . .
H9A H -0.183(2) 0.001(4) 0.151(2) 0.040 Uiso 1 1 d . U . . .
N10 N 0.0202(2) 0.0619(4) 0.2743(2) 0.0352(7) Uani 1 1 d . . . . .
H10A H 0.073(2) 0.103(4) 0.327(2) 0.042 Uiso 1 1 d . U . . .
H10B H 0.036(3) 0.075(5) 0.217(2) 0.042 Uiso 1 1 d . U . . .
O1 O 0.36121(14) 0.4054(3) 0.94279(12) 0.0292(5) Uani 1 1 d . . . . .
O2 O 0.40754(14) 0.5909(3) 0.53872(13) 0.0274(5) Uani 1 1 d . . . . .
O3 O -0.00162(14) 0.2770(3) 0.55362(13) 0.0266(5) Uani 1 1 d . . . . .
O4 O 0.11430(15) 0.3106(3) 0.44880(13) 0.0305(5) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.305(3) . ?
C1 N2 1.380(3) . ?
C1 C4 1.470(3) . ?
C2 N2 1.289(3) . ?
C2 O1 1.336(3) . ?
C2 C2 1.465(5) 3_667 ?
C3 N3 1.313(3) . ?
C3 N5 1.374(3) . ?
C3 C4 1.434(3) . ?
C4 N4 1.301(3) . ?
C5 N10 1.325(3) . ?
C5 N8 1.328(3) . ?
C5 N9 1.337(3) . ?
C6 N7 1.292(3) . ?
C6 N9 1.358(4) . ?
C6 H6 0.9500 . ?
N1 O1 1.410(2) . ?
N3 O2 1.395(2) . ?
N4 O2 1.373(2) . ?
N5 N6 1.311(3) . ?
N6 O4 1.256(2) . ?
N6 O3 1.271(3) . ?
N7 N8 1.382(3) . ?
N8 H8A 0.91(3) . ?
N9 H9A 0.82(3) . ?
N10 H10A 0.88(3) . ?
N10 H10B 0.83(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 N2 115.4(2) . . ?
N1 C1 C4 122.9(2) . . ?
N2 C1 C4 121.7(2) . . ?
N2 C2 O1 115.2(2) . . ?
N2 C2 C2 128.3(3) . 3_667 ?
O1 C2 C2 116.5(3) . 3_667 ?
N3 C3 N5 130.2(2) . . ?
N3 C3 C4 107.9(2) . . ?
N5 C3 C4 121.7(2) . . ?
N4 C4 C3 110.0(2) . . ?
N4 C4 C1 119.2(2) . . ?
C3 C4 C1 130.8(2) . . ?
N10 C5 N8 126.8(2) . . ?
N10 C5 N9 127.6(3) . . ?
N8 C5 N9 105.5(2) . . ?
N7 C6 N9 112.4(3) . . ?
N7 C6 H6 123.8 . . ?
N9 C6 H6 123.8 . . ?
C1 N1 O1 102.90(18) . . ?
C2 N2 C1 100.9(2) . . ?
C3 N3 O2 105.48(18) . . ?
C4 N4 O2 105.34(19) . . ?
N6 N5 C3 116.1(2) . . ?
O4 N6 O3 119.7(2) . . ?
O4 N6 N5 124.1(2) . . ?
O3 N6 N5 116.21(19) . . ?
C6 N7 N8 102.9(2) . . ?
C5 N8 N7 112.0(2) . . ?
C5 N8 H8A 126.1(16) . . ?
N7 N8 H8A 121.7(16) . . ?
C5 N9 C6 107.2(2) . . ?
C5 N9 H9A 125(2) . . ?
C6 N9 H9A 128(2) . . ?
C5 N10 H10A 117(2) . . ?
C5 N10 H10B 120(2) . . ?
H10A N10 H10B 115(3) . . ?
C2 O1 N1 105.50(17) . . ?
N4 O2 N3 111.22(16) . . ?

_refine_diff_density_max         0.210
_refine_diff_density_min         -0.263
_refine_diff_density_rms         0.064

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

data_1_CCDC4
_database_code_depnum_ccdc_archive 'CCDC 1816900'
_audit_update_record             
;
2018-01-15 deposited with the CCDC.
2018-06-29 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(H4 N O), C8 N12 O8'
_chemical_formula_sum            'C8 H8 N14 O10'
_chemical_formula_weight         460.28

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                   14.701(3)
_cell_length_b                   4.1634(7)
_cell_length_c                   14.1870(19)
_cell_angle_alpha                90
_cell_angle_beta                 110.503(7)
_cell_angle_gamma                90
_cell_volume                     813.3(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    557
_cell_measurement_theta_min      2.96
_cell_measurement_theta_max      24.37

_exptl_crystal_description       sheet
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.879
_exptl_crystal_F_000             468
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.310
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    0.171
_shelx_estimated_absorpt_T_min   0.949
_shelx_estimated_absorpt_T_max   0.997
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6022
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_process_details   'SADABS (Bruker, 2014)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'PHOTON 100 CMOS detector'
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            3771
_diffrn_reflns_av_unetI/netI     0.1126
_diffrn_reflns_av_R_equivalents  0.1057
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.900
_diffrn_reflns_theta_max         25.253
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             1451
_reflns_number_gt                858
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0322P)²+0.7293P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1451
_refine_ls_number_parameters     157
_refine_ls_number_restraints     7
_refine_ls_R_factor_all          0.1322
_refine_ls_R_factor_gt           0.0606
_refine_ls_wR_factor_ref         0.1195
_refine_ls_wR_factor_gt          0.0982
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_restrained_S_all      1.045
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.6283(3) 0.9552(11) 0.3960(3) 0.0150(10) Uani 1 1 d . . . . .
C2 C 0.5373(3) 0.9706(11) 0.4783(3) 0.0125(9) Uani 1 1 d . . . . .
C3 C 0.7531(3) 0.9061(10) 0.3014(3) 0.0137(10) Uani 1 1 d . . . . .
C4 C 0.6686(3) 1.0277(10) 0.3179(3) 0.0148(10) Uani 1 1 d . . . . .
N1 N 0.6666(2) 0.7424(9) 0.4665(2) 0.0188(9) Uani 1 1 d . . . . .
N2 N 0.5468(2) 1.1099(9) 0.4012(2) 0.0154(9) Uani 1 1 d . . . . .
N3 N 0.7582(2) 1.0437(9) 0.2200(2) 0.0181(9) Uani 1 1 d . . . . .
N4 N 0.6239(2) 1.2344(9) 0.2485(3) 0.0213(9) Uani 1 1 d . . . . .
N5 N 0.8124(2) 0.6850(8) 0.3660(2) 0.0147(8) Uani 1 1 d . . . . .
N6 N 0.8848(2) 0.5731(8) 0.3403(2) 0.0163(9) Uani 1 1 d . . . . .
N7 N 0.8711(2) 0.4926(9) 0.5889(2) 0.0156(9) Uani 1 1 d D . . . .
H7A H 0.8289(19) 0.619(8) 0.540(2) 0.019 Uiso 1 1 d D U . . .
H7B H 0.849(2) 0.463(10) 0.6410(19) 0.019 Uiso 1 1 d D U . . .
H7C H 0.9319(18) 0.589(9) 0.612(2) 0.019 Uiso 1 1 d D U . . .
O1 O 0.60431(19) 0.7473(7) 0.5225(2) 0.0189(7) Uani 1 1 d . . . . .
O2 O 0.6775(2) 1.2486(7) 0.1867(2) 0.0224(8) Uani 1 1 d . . . . .
O3 O 0.93849(19) 0.3597(7) 0.3995(2) 0.0184(7) Uani 1 1 d . . . . .
O4 O 0.9038(2) 0.6596(8) 0.2653(2) 0.0271(8) Uani 1 1 d . . . . .
O5 O 0.8726(2) 0.1888(8) 0.5457(2) 0.0264(8) Uani 1 1 d D . . . .
H5 H 0.893(3) 0.238(12) 0.500(2) 0.032 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
C1 N1 1.307(5) . ?
C1 N2 1.385(5) . ?
C1 C4 1.458(5) . ?
C2 N2 1.290(5) . ?
C2 O1 1.340(5) . ?
C2 C2 1.452(7) 3_676 ?
C3 N3 1.315(5) . ?
C3 N5 1.374(5) . ?
C3 C4 1.435(6) . ?
C4 N4 1.299(5) . ?
N1 O1 1.408(4) . ?
N3 O2 1.402(4) . ?
N4 O2 1.369(4) . ?
N5 N6 1.324(4) . ?
N6 O4 1.245(4) . ?
N6 O3 1.286(4) . ?
N7 O5 1.409(5) . ?
N7 H7A 0.92(2) . ?
N7 H7B 0.92(2) . ?
N7 H7C 0.93(2) . ?
O5 H5 0.826(19) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 N2 115.0(3) . . ?
N1 C1 C4 122.8(3) . . ?
N2 C1 C4 122.2(4) . . ?
N2 C2 O1 115.3(3) . . ?
N2 C2 C2 127.3(5) . 3_676 ?
O1 C2 C2 117.3(5) . 3_676 ?
N3 C3 N5 131.3(4) . . ?
N3 C3 C4 108.0(4) . . ?
N5 C3 C4 120.8(3) . . ?
N4 C4 C3 110.3(4) . . ?
N4 C4 C1 118.7(4) . . ?
C3 C4 C1 131.0(4) . . ?
C1 N1 O1 103.4(3) . . ?
C2 N2 C1 100.9(3) . . ?
C3 N3 O2 105.0(3) . . ?
C4 N4 O2 105.2(3) . . ?
N6 N5 C3 115.9(3) . . ?
O4 N6 O3 119.3(3) . . ?
O4 N6 N5 125.1(3) . . ?
O3 N6 N5 115.6(3) . . ?
O5 N7 H7A 107(2) . . ?
O5 N7 H7B 107(3) . . ?
H7A N7 H7B 111(2) . . ?
O5 N7 H7C 113(2) . . ?
H7A N7 H7C 109(2) . . ?
H7B N7 H7C 110(2) . . ?
C2 O1 N1 105.3(3) . . ?
N4 O2 N3 111.5(3) . . ?
N7 O5 H5 101(4) . . ?

_refine_diff_density_max         0.392
_refine_diff_density_min         -0.326
_refine_diff_density_rms         0.084

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

data_1_CCDC5
_database_code_depnum_ccdc_archive 'CCDC 1816904'
_audit_update_record             
;
2018-01-15 deposited with the CCDC.
2018-06-29 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         'C H8 N4 O, C8 N12 O8, H2 O'
_chemical_formula_sum            'C9 H10 N16 O10'
_chemical_formula_weight         502.33

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           15
_space_group_name_H-M_alt        'C 2/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'
'-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                   28.666(3)
_cell_length_b                   4.5532(5)
_cell_length_c                   14.0610(16)
_cell_angle_alpha                90
_cell_angle_beta                 95.658(4)
_cell_angle_gamma                90
_cell_volume                     1826.3(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    1115
_cell_measurement_theta_min      3.11
_cell_measurement_theta_max      25.06

_exptl_crystal_description       sheet
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.827
_exptl_crystal_F_000             1024
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.190
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    0.164
_shelx_estimated_absorpt_T_min   0.949
_shelx_estimated_absorpt_T_max   0.997
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6422
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_process_details   'SADABS (Bruker, 2014)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'PHOTON 100 CMOS detector'
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4703
_diffrn_reflns_av_unetI/netI     0.0835
_diffrn_reflns_av_R_equivalents  0.0809
_diffrn_reflns_limit_h_min       -34
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.912
_diffrn_reflns_theta_max         25.024
_diffrn_reflns_theta_full        25.024
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             1614
_reflns_number_gt                1001
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0565P)²+2.3444P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1614
_refine_ls_number_parameters     202
_refine_ls_number_restraints     90
_refine_ls_R_factor_all          0.1185
_refine_ls_R_factor_gt           0.0629
_refine_ls_wR_factor_ref         0.1414
_refine_ls_wR_factor_gt          0.1186
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_restrained_S_all      1.034
_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
C1 C 0.19243(12) 0.3153(8) 0.3311(3) 0.0255(9) Uani 1 1 d . . . . .
C2 C 0.23364(11) 0.2826(8) 0.4588(3) 0.0210(8) Uani 1 1 d . . . . .
C3 C 0.13218(12) 0.3814(8) 0.1804(3) 0.0205(8) Uani 1 1 d . . . . .
C4 C 0.17262(12) 0.2562(8) 0.2339(3) 0.0205(8) Uani 1 1 d . . . . .
N2 N 0.22812(10) 0.1619(7) 0.3774(2) 0.0261(8) Uani 1 1 d . . . . .
N3 N 0.12707(11) 0.2593(7) 0.0959(2) 0.0266(8) Uani 1 1 d . . . . .
N4 N 0.19149(11) 0.0636(7) 0.1819(2) 0.0300(8) Uani 1 1 d . . . . .
N5 N 0.10603(10) 0.5918(6) 0.2211(2) 0.0232(7) Uani 1 1 d . . . . .
N6 N 0.06861(10) 0.6903(7) 0.1698(2) 0.0268(8) Uani 1 1 d . . . . .
O2 O 0.16431(10) 0.0605(6) 0.09619(19) 0.0356(7) Uani 1 1 d . . . . .
O3 O 0.05552(9) 0.6051(7) 0.08734(19) 0.0441(9) Uani 1 1 d . . . . .
O4 O 0.04548(9) 0.8830(6) 0.20950(18) 0.0367(8) Uani 1 1 d . . . . .
O1 O 0.2131(2) 0.5510(13) 0.4594(4) 0.0246(14) Uani 0.5 1 d . U P A 1
N1 N 0.1859(2) 0.5775(14) 0.3713(5) 0.0237(14) Uani 0.5 1 d . U P A 1
N7 N 0.0774(3) 0.680(2) 0.4076(8) 0.021(3) Uiso 0.5 1 d D U P B 1
H7A H 0.0979 0.7009 0.3635 0.031 Uiso 0.5 1 d R U P B 1
H7B H 0.0932 0.6589 0.4657 0.031 Uiso 0.5 1 d R U P B 1
H7C H 0.0602 0.8455 0.4080 0.031 Uiso 0.5 1 d R U P B 1
C5 C 0.0703(2) 0.1757(11) 0.4067(5) 0.0176(14) Uani 0.5 1 d D U P B 1
N8 N 0.04696(19) 0.4348(12) 0.3893(4) 0.0184(12) Uani 0.5 1 d D U P B 1
H8A H 0.0209(14) 0.511(14) 0.399(5) 0.022 Uiso 0.5 1 d D U P C 1
N9 N 0.04098(18) -0.0633(12) 0.4129(4) 0.0160(12) Uani 0.5 1 d D U P B 1
H9A H 0.0180 -0.0561 0.3644 0.019 Uiso 0.5 1 d R U P B 1
N10 N 0.0678(3) -0.326(2) 0.4088(8) 0.019(3) Uiso 0.5 1 d D U P B 1
H10A H 0.0982 -0.2866 0.4033 0.028 Uiso 0.5 1 d R U P B 1
H10B H 0.0563 -0.4387 0.3594 0.028 Uiso 0.5 1 d R U P B 1
H10C H 0.0661 -0.4283 0.4631 0.028 Uiso 0.5 1 d R U P B 1
O5 O 0.11252(16) 0.1594(10) 0.4173(4) 0.0248(12) Uani 0.5 1 d D U P B 1
O1' O 0.1957(2) 0.4439(15) 0.4791(5) 0.0307(15) Uani 0.5 1 d . U P A 2
N1' N 0.1665(3) 0.4519(17) 0.3923(5) 0.0319(16) Uani 0.5 1 d . U P A 2
O6 O 0.01683(16) 0.1463(10) 0.4079(3) 0.0225(11) Uani 0.5 1 d . U P D 2
H6D H -0.0023 0.0520 0.3692 0.027 Uiso 0.5 1 d R U P D 2
H6E H 0.0095 0.3116 0.4303 0.027 Uiso 0.5 1 d R U P D 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
C1 N1 1.342(7) . ?
C1 N1' 1.344(8) . ?
C1 N2 1.352(4) . ?
C1 C4 1.452(5) . ?
C2 N2 1.265(4) . ?
C2 O1 1.357(7) . ?
C2 O1' 1.365(7) . ?
C2 C2 1.447(7) 7_556 ?
C3 N3 1.306(4) . ?
C3 N5 1.376(4) . ?
C3 C4 1.437(5) . ?
C4 N4 1.295(4) . ?
N3 O2 1.399(4) . ?
N4 O2 1.369(4) . ?
N5 N6 1.312(4) . ?
N6 O3 1.244(4) . ?
N6 O4 1.263(4) . ?
O1 N1 1.401(8) . ?
N7 N10 0.277(13) 1_565 ?
N7 N8 1.424(10) . ?
N7 N9 1.574(11) 1_565 ?
N7 H7A 0.8999 . ?
N7 H7B 0.9000 . ?
N7 H7C 0.9002 . ?
C5 O5 1.207(8) . ?
C5 N8 1.367(7) . ?
C5 N9 1.383(7) . ?
N8 N10 1.260(10) 1_565 ?
N8 H8A 0.85(2) . ?
N9 N10 1.426(10) . ?
N9 N7 1.574(11) 1_545 ?
N9 H9A 0.9001 . ?
N10 N7 0.277(13) 1_545 ?
N10 N8 1.260(10) 1_545 ?
N10 H10A 0.8999 . ?
N10 H10B 0.9000 . ?
N10 H10C 0.9000 . ?
O1' N1' 1.411(9) . ?
O6 H6D 0.8499 . ?
O6 H6E 0.8500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 N2 112.8(4) . . ?
N1' C1 N2 111.8(4) . . ?
N1 C1 C4 120.2(4) . . ?
N1' C1 C4 119.9(4) . . ?
N2 C1 C4 124.4(3) . . ?
N2 C2 O1 112.4(4) . . ?
N2 C2 O1' 113.0(4) . . ?
N2 C2 C2 130.4(4) . 7_556 ?
O1 C2 C2 115.3(5) . 7_556 ?
O1' C2 C2 114.2(5) . 7_556 ?
N3 C3 N5 131.1(3) . . ?
N3 C3 C4 108.7(3) . . ?
N5 C3 C4 120.2(3) . . ?
N4 C4 C3 109.4(3) . . ?
N4 C4 C1 120.7(3) . . ?
C3 C4 C1 129.8(3) . . ?
C2 N2 C1 103.4(3) . . ?
C3 N3 O2 104.8(3) . . ?
C4 N4 O2 105.8(3) . . ?
N6 N5 C3 117.3(3) . . ?
O3 N6 O4 120.3(3) . . ?
O3 N6 N5 124.1(3) . . ?
O4 N6 N5 115.5(3) . . ?
N4 O2 N3 111.3(2) . . ?
C2 O1 N1 106.0(5) . . ?
C1 N1 O1 102.0(5) . . ?
N10 N7 N8 49(4) 1_565 . ?
N10 N7 N9 53(4) 1_565 1_565 ?
N8 N7 N9 101.2(6) . 1_565 ?
N10 N7 H7A 140.2 1_565 . ?
N8 N7 H7A 112.9 . . ?
N9 N7 H7A 115.8 1_565 . ?
N10 N7 H7B 110.2 1_565 . ?
N8 N7 H7B 109.0 . . ?
N9 N7 H7B 108.2 1_565 . ?
H7A N7 H7B 109.4 . . ?
N10 N7 H7C 62.4 1_565 . ?
N8 N7 H7C 109.4 . . ?
N9 N7 H7C 9.1 1_565 . ?
H7A N7 H7C 108.0 . . ?
H7B N7 H7C 108.0 . . ?
O5 C5 N8 122.8(5) . . ?
O5 C5 N9 123.5(5) . . ?
N8 C5 N9 113.7(6) . . ?
N10 N8 C5 119.6(6) 1_565 . ?
N10 N8 N7 9.6(7) 1_565 . ?
C5 N8 N7 111.4(6) . . ?
N10 N8 H8A 91(5) 1_565 . ?
C5 N8 H8A 138(5) . . ?
N7 N8 H8A 101(5) . . ?
C5 N9 N10 108.9(5) . . ?
C5 N9 N7 99.9(5) . 1_545 ?
N10 N9 N7 9.0(6) . 1_545 ?
C5 N9 H9A 109.1 . . ?
N10 N9 H9A 110.9 . . ?
N7 N9 H9A 115.4 1_545 . ?
N7 N10 N8 121(4) 1_545 1_545 ?
N7 N10 N9 118(4) 1_545 . ?
N8 N10 N9 119.1(7) 1_545 . ?
N7 N10 H10A 6.1 1_545 . ?
N8 N10 H10A 126.6 1_545 . ?
N9 N10 H10A 111.6 . . ?
N7 N10 H10B 107.2 1_545 . ?
N8 N10 H10B 37.7 1_545 . ?
N9 N10 H10B 110.6 . . ?
H10A N10 H10B 109.3 . . ?
N7 N10 H10C 103.9 1_545 . ?
N8 N10 H10C 70.8 1_545 . ?
N9 N10 H10C 108.9 . . ?
H10A N10 H10C 108.2 . . ?
H10B N10 H10C 108.2 . . ?
C2 O1' N1' 104.5(5) . . ?
C1 N1' O1' 102.9(5) . . ?
H6D O6 H6E 121.1 . . ?

_refine_diff_density_max         0.270
_refine_diff_density_min         -0.367
_refine_diff_density_rms         0.073

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

data_1_CCDC6
_database_code_depnum_ccdc_archive 'CCDC 1816901'
_audit_update_record             
;
2018-01-15 deposited with the CCDC.
2018-06-29 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(C2 H6 N5), C8 N12 O8, 2(H2 O)'
_chemical_formula_sum            'C12 H16 N22 O10'
_chemical_formula_weight         628.47

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                   7.0523(7)
_cell_length_b                   19.0738(19)
_cell_length_c                   9.4159(12)
_cell_angle_alpha                90
_cell_angle_beta                 111.758(4)
_cell_angle_gamma                90
_cell_volume                     1176.3(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    171(2)
_cell_measurement_reflns_used    1610
_cell_measurement_theta_min      3.16
_cell_measurement_theta_max      25.32

_exptl_crystal_description       column
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.774
_exptl_crystal_F_000             644
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.270
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.130
_exptl_absorpt_coefficient_mu    0.154
_shelx_estimated_absorpt_T_min   0.960
_shelx_estimated_absorpt_T_max   0.980
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6249
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_process_details   'SADABS (Bruker, 2014)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      171(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'PHOTON 100 CMOS detector'
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5741
_diffrn_reflns_av_unetI/netI     0.0706
_diffrn_reflns_av_R_equivalents  0.0612
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         3.289
_diffrn_reflns_theta_max         25.376
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             2139
_reflns_number_gt                1508
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0412P)²+0.0231P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2139
_refine_ls_number_parameters     223
_refine_ls_number_restraints     9
_refine_ls_R_factor_all          0.0868
_refine_ls_R_factor_gt           0.0486
_refine_ls_wR_factor_ref         0.0978
_refine_ls_wR_factor_gt          0.0865
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_restrained_S_all      1.041
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C -0.1285(4) 0.92987(13) 0.5980(3) 0.0131(6) Uani 1 1 d . . . . .
C2 C -0.3958(4) 0.98680(13) 0.5288(3) 0.0138(6) Uani 1 1 d . . . . .
C3 C 0.2251(4) 0.86351(13) 0.6967(3) 0.0152(6) Uani 1 1 d . . . . .
C4 C 0.0066(4) 0.86938(12) 0.6226(3) 0.0137(6) Uani 1 1 d . . . . .
C5 C 0.6859(4) 0.19513(12) 0.6997(3) 0.0148(6) Uani 1 1 d . . . . .
C6 C 0.8623(4) 0.12683(12) 0.8878(3) 0.0133(6) Uani 1 1 d . . . . .
N1 N -0.0639(3) 0.99318(11) 0.6453(2) 0.0176(5) Uani 1 1 d . . . . .
N2 N -0.3367(3) 0.92324(10) 0.5236(2) 0.0138(5) Uani 1 1 d . . . . .
N3 N 0.2731(3) 0.79707(11) 0.6928(2) 0.0195(5) Uani 1 1 d . . . . .
N4 N -0.0719(3) 0.80832(10) 0.5730(3) 0.0197(5) Uani 1 1 d . . . . .
N5 N 0.3446(3) 0.92189(10) 0.7516(2) 0.0170(5) Uani 1 1 d . . . . .
N6 N 0.5442(3) 0.91011(11) 0.8116(2) 0.0169(5) Uani 1 1 d . . . . .
N7 N 1.0000(3) 0.16144(11) 0.8545(2) 0.0171(5) Uani 1 1 d . . . . .
N8 N 0.8831(3) 0.20360(11) 0.7307(2) 0.0175(5) Uani 1 1 d D . . . .
H8A H 0.939(4) 0.2383(12) 0.712(3) 0.021 Uiso 1 1 d D U . . .
N9 N 0.6684(3) 0.14525(11) 0.7951(2) 0.0146(5) Uani 1 1 d D . . . .
H9A H 0.559(3) 0.1306(13) 0.797(3) 0.017 Uiso 1 1 d D U . . .
N10 N 0.5350(3) 0.23041(12) 0.5970(3) 0.0212(6) Uani 1 1 d D . . . .
H10A H 0.414(3) 0.2139(13) 0.563(3) 0.025 Uiso 1 1 d D U . . .
H10B H 0.565(4) 0.2590(13) 0.540(3) 0.025 Uiso 1 1 d D U . . .
N11 N 0.9017(3) 0.08150(12) 1.0051(3) 0.0196(5) Uani 1 1 d D . . . .
H11A H 0.808(3) 0.0532(12) 1.001(3) 0.024 Uiso 1 1 d D U . . .
H11B H 1.028(3) 0.0716(14) 1.053(3) 0.024 Uiso 1 1 d D U . . .
O1 O -0.2456(2) 1.03261(8) 0.59778(19) 0.0169(4) Uani 1 1 d . . . . .
O2 O 0.0887(3) 0.76226(9) 0.6146(2) 0.0224(5) Uani 1 1 d . . . . .
O3 O 0.6549(3) 0.96404(9) 0.8469(2) 0.0212(5) Uani 1 1 d . . . . .
O4 O 0.6222(3) 0.85090(9) 0.8310(2) 0.0255(5) Uani 1 1 d . . . . .
O5 O 0.3420(3) 0.08669(11) 0.8242(3) 0.0320(5) Uani 1 1 d D . . . .
H5C H 0.249(4) 0.1089(15) 0.840(4) 0.038 Uiso 1 1 d D U . . .
H5D H 0.303(5) 0.0464(10) 0.802(3) 0.038 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
C1 N1 1.309(3) . ?
C1 N2 1.378(3) . ?
C1 C4 1.459(3) . ?
C2 N2 1.289(3) . ?
C2 O1 1.341(3) . ?
C2 C2 1.455(5) 3_476 ?
C3 N3 1.316(3) . ?
C3 N5 1.376(3) . ?
C3 C4 1.441(3) . ?
C4 N4 1.300(3) . ?
C5 N8 1.321(3) . ?
C5 N10 1.326(3) . ?
C5 N9 1.345(3) . ?
C6 N7 1.305(3) . ?
C6 N11 1.348(3) . ?
C6 N9 1.368(3) . ?
N1 O1 1.408(3) . ?
N3 O2 1.402(3) . ?
N4 O2 1.371(3) . ?
N5 N6 1.328(3) . ?
N6 O4 1.240(2) . ?
N6 O3 1.259(3) . ?
N7 N8 1.405(3) . ?
N8 H8A 0.82(2) . ?
N9 H9A 0.83(2) . ?
N10 H10A 0.854(17) . ?
N10 H10B 0.846(18) . ?
N11 H11A 0.844(17) . ?
N11 H11B 0.856(18) . ?
O5 H5C 0.837(18) . ?
O5 H5D 0.817(17) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 N2 115.4(2) . . ?
N1 C1 C4 123.4(2) . . ?
N2 C1 C4 121.2(2) . . ?
N2 C2 O1 115.0(2) . . ?
N2 C2 C2 127.4(3) . 3_476 ?
O1 C2 C2 117.6(3) . 3_476 ?
N3 C3 N5 131.4(2) . . ?
N3 C3 C4 107.6(2) . . ?
N5 C3 C4 121.0(2) . . ?
N4 C4 C3 109.9(2) . . ?
N4 C4 C1 119.0(2) . . ?
C3 C4 C1 131.0(2) . . ?
N8 C5 N10 126.4(2) . . ?
N8 C5 N9 106.8(2) . . ?
N10 C5 N9 126.8(2) . . ?
N7 C6 N11 125.1(2) . . ?
N7 C6 N9 112.0(2) . . ?
N11 C6 N9 122.8(2) . . ?
C1 N1 O1 102.92(18) . . ?
C2 N2 C1 101.1(2) . . ?
C3 N3 O2 105.81(19) . . ?
C4 N4 O2 105.94(19) . . ?
N6 N5 C3 115.34(19) . . ?
O4 N6 O3 120.5(2) . . ?
O4 N6 N5 124.0(2) . . ?
O3 N6 N5 115.48(19) . . ?
C6 N7 N8 103.24(19) . . ?
C5 N8 N7 111.0(2) . . ?
C5 N8 H8A 126.7(19) . . ?
N7 N8 H8A 117.5(19) . . ?
C5 N9 C6 106.9(2) . . ?
C5 N9 H9A 124.9(18) . . ?
C6 N9 H9A 128.2(18) . . ?
C5 N10 H10A 120.4(18) . . ?
C5 N10 H10B 117.8(19) . . ?
H10A N10 H10B 117(3) . . ?
C6 N11 H11A 116.9(18) . . ?
C6 N11 H11B 115.7(19) . . ?
H11A N11 H11B 122(3) . . ?
C2 O1 N1 105.56(17) . . ?
N4 O2 N3 110.74(17) . . ?
H5C O5 H5D 108(3) . . ?

_refine_diff_density_max         0.324
_refine_diff_density_min         -0.307
_refine_diff_density_rms         0.064

