# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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 1477790'
_audit_update_record             
;
2016-05-03 deposited with the CCDC.
2017-09-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H4 N16 O20'
_chemical_formula_sum            'C10 H4 N16 O20'
_chemical_formula_weight         668.29

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

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P2(1)/c  '
_symmetry_space_group_name_Hall  '-P 2ybc  '

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

_cell_length_a                   17.477(3)
_cell_length_b                   6.0354(7)
_cell_length_c                   21.647(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 94.787(6)
_cell_angle_gamma                90.00
_cell_volume                     2275.3(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    1559
_cell_measurement_theta_min      3.13
_cell_measurement_theta_max      25.25

_exptl_crystal_description       needle
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.03
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.951
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1344
_exptl_absorpt_coefficient_mu    0.190
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5610
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_process_details   'SADABS (Bruker, 2013)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  'TRIUMPH curved crystal monochromator'
_diffrn_measurement_device_type  'PHOTON100 CMOS detector'
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12671
_diffrn_reflns_av_R_equivalents  0.1481
_diffrn_reflns_av_sigmaI/netI    0.1487
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         3.13
_diffrn_reflns_theta_max         24.50
_reflns_number_total             3716
_reflns_number_gt                1792
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0168P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3716
_refine_ls_number_parameters     415
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1743
_refine_ls_R_factor_gt           0.0607
_refine_ls_wR_factor_ref         0.0959
_refine_ls_wR_factor_gt          0.0737
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_restrained_S_all      1.011
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.2588(3) 0.3294(7) 0.2868(2) 0.0155(11) Uani 1 1 d . . .
C2 C 0.2465(3) 0.6454(7) 0.2082(2) 0.0146(11) Uani 1 1 d . . .
C3 C 0.2298(2) 0.0870(7) 0.3805(2) 0.0160(12) Uani 1 1 d . . .
C4 C 0.2680(3) 0.1383(7) 0.3276(2) 0.0147(11) Uani 1 1 d . . .
C5 C 0.1020(2) 0.1065(7) 0.4237(2) 0.0211(12) Uani 1 1 d . . .
H5A H 0.0918 0.1488 0.4664 0.025 Uiso 1 1 calc R . .
H5B H 0.1071 -0.0567 0.4223 0.025 Uiso 1 1 calc R . .
C6 C 0.0350(3) 0.1774(7) 0.3793(2) 0.0214(12) Uani 1 1 d . . .
C7 C 0.2729(3) 0.8761(7) 0.1111(2) 0.0169(12) Uani 1 1 d . . .
C8 C 0.2362(3) 0.8337(7) 0.1657(2) 0.0154(11) Uani 1 1 d . . .
C9 C 0.3987(2) 0.8270(6) 0.0678(2) 0.0159(11) Uani 1 1 d . . .
H9A H 0.3988 0.9907 0.0705 0.019 Uiso 1 1 calc R . .
H9B H 0.4073 0.7861 0.0246 0.019 Uiso 1 1 calc R . .
C10 C 0.4650(3) 0.7357(6) 0.1114(2) 0.0174(12) Uani 1 1 d . . .
N1 N 0.2050(2) 0.4634(5) 0.29584(18) 0.0215(10) Uani 1 1 d . . .
N2 N 0.2988(2) 0.5099(5) 0.19860(18) 0.0220(10) Uani 1 1 d . . .
N3 N 0.2505(2) -0.1084(6) 0.40122(19) 0.0232(10) Uani 1 1 d . . .
N4 N 0.3141(2) -0.0224(6) 0.31662(19) 0.0260(11) Uani 1 1 d . . .
N5 N 0.1733(2) 0.2067(5) 0.40869(18) 0.0175(10) Uani 1 1 d . . .
N6 N 0.2017(2) 0.3902(6) 0.44568(19) 0.0208(10) Uani 1 1 d . . .
N7 N 0.0506(2) 0.1482(7) 0.3118(2) 0.0293(11) Uani 1 1 d . . .
N8 N -0.0352(2) 0.0350(7) 0.3886(2) 0.0341(12) Uani 1 1 d . . .
N9 N 0.0109(3) 0.4150(7) 0.3892(2) 0.0328(12) Uani 1 1 d . . .
N10 N 0.2528(2) 1.0702(6) 0.08975(19) 0.0230(10) Uani 1 1 d . . .
N11 N 0.1925(2) 1.0022(6) 0.17777(19) 0.0243(10) Uani 1 1 d . . .
N12 N 0.3248(2) 0.7461(5) 0.08176(17) 0.0143(9) Uani 1 1 d . . .
N13 N 0.2918(3) 0.5744(6) 0.04317(19) 0.0235(10) Uani 1 1 d . . .
N14 N 0.5371(2) 0.8625(7) 0.1007(2) 0.0313(11) Uani 1 1 d . . .
N15 N 0.4813(3) 0.4902(6) 0.1007(2) 0.0270(11) Uani 1 1 d . . .
N16 N 0.4525(2) 0.7655(6) 0.1791(2) 0.0253(11) Uani 1 1 d . . .
O1 O 0.19848(18) 0.6487(5) 0.25360(16) 0.0272(9) Uani 1 1 d . . .
O2 O 0.30915(18) 0.3337(5) 0.24327(16) 0.0303(9) Uani 1 1 d . . .
O3 O 0.30353(18) -0.1782(4) 0.36232(16) 0.0269(9) Uani 1 1 d . . .
O4 O 0.1545(2) 0.4852(5) 0.47379(17) 0.0327(9) Uani 1 1 d . . .
O5 O 0.26890(19) 0.4321(4) 0.44231(15) 0.0244(9) Uani 1 1 d . . .
O6 O 0.0954(2) 0.0011(5) 0.30219(16) 0.0322(9) Uani 1 1 d . . .
O7 O 0.0164(2) 0.2673(6) 0.27408(18) 0.0532(12) Uani 1 1 d . . .
O8 O -0.0825(2) 0.0109(6) 0.3452(2) 0.0613(13) Uani 1 1 d . . .
O9 O -0.0372(2) -0.0461(7) 0.43937(19) 0.0550(12) Uani 1 1 d . . .
O10 O -0.0435(2) 0.4403(6) 0.4189(2) 0.0714(15) Uani 1 1 d . . .
O11 O 0.0506(2) 0.5554(5) 0.36929(18) 0.0431(11) Uani 1 1 d . . .
O12 O 0.20321(19) 1.1508(5) 0.13025(16) 0.0281(9) Uani 1 1 d . . .
O13 O 0.22339(19) 0.5443(4) 0.04645(15) 0.0251(9) Uani 1 1 d . . .
O14 O 0.3355(2) 0.4733(5) 0.01337(16) 0.0319(9) Uani 1 1 d . . .
O15 O 0.5481(2) 0.8946(6) 0.04701(19) 0.0488(11) Uani 1 1 d . . .
O16 O 0.5774(2) 0.9232(6) 0.1455(2) 0.0485(12) Uani 1 1 d . . .
O17 O 0.4327(2) 0.3654(5) 0.11667(18) 0.0410(10) Uani 1 1 d . . .
O18 O 0.5383(2) 0.4440(5) 0.07641(19) 0.0492(11) Uani 1 1 d . . .
O19 O 0.41196(19) 0.9219(5) 0.19032(15) 0.0300(9) Uani 1 1 d . . .
O20 O 0.4836(2) 0.6339(6) 0.21531(17) 0.0457(11) 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 1.267(5) . ?
C1 O2 1.343(5) . ?
C1 C4 1.453(6) . ?
C2 N2 1.257(5) . ?
C2 O1 1.344(5) . ?
C2 C8 1.465(6) . ?
C3 N3 1.303(5) . ?
C3 N5 1.403(5) . ?
C3 C4 1.407(6) . ?
C4 N4 1.296(5) . ?
C5 N5 1.445(5) . ?
C5 C6 1.512(6) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 N9 1.515(5) . ?
C6 N7 1.520(6) . ?
C6 N8 1.525(6) . ?
C7 N10 1.297(5) . ?
C7 N12 1.392(5) . ?
C7 C8 1.414(6) . ?
C8 N11 1.311(5) . ?
C9 N12 1.437(5) . ?
C9 C10 1.534(6) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 N14 1.510(6) . ?
C10 N16 1.511(6) . ?
C10 N15 1.530(5) . ?
N1 O1 1.443(4) . ?
N2 O2 1.439(4) . ?
N3 O3 1.369(5) . ?
N4 O3 1.388(4) . ?
N5 N6 1.431(5) . ?
N6 O5 1.209(4) . ?
N6 O4 1.210(5) . ?
N7 O7 1.208(5) . ?
N7 O6 1.213(5) . ?
N8 O9 1.207(5) . ?
N8 O8 1.207(5) . ?
N9 O11 1.199(5) . ?
N9 O10 1.201(5) . ?
N10 O12 1.372(5) . ?
N11 O12 1.389(4) . ?
N12 N13 1.423(5) . ?
N13 O14 1.206(5) . ?
N13 O13 1.217(5) . ?
N14 O16 1.207(5) . ?
N14 O15 1.209(5) . ?
N15 O18 1.198(5) . ?
N15 O17 1.207(5) . ?
N16 O20 1.212(4) . ?
N16 O19 1.217(4) . ?

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 O2 129.4(4) . . ?
N1 C1 C4 117.3(4) . . ?
O2 C1 C4 113.3(4) . . ?
N2 C2 O1 129.7(4) . . ?
N2 C2 C8 117.0(4) . . ?
O1 C2 C8 113.3(4) . . ?
N3 C3 N5 120.1(4) . . ?
N3 C3 C4 110.0(4) . . ?
N5 C3 C4 129.8(4) . . ?
N4 C4 C3 109.2(4) . . ?
N4 C4 C1 121.5(5) . . ?
C3 C4 C1 129.3(4) . . ?
N5 C5 C6 112.1(4) . . ?
N5 C5 H5A 109.2 . . ?
C6 C5 H5A 109.2 . . ?
N5 C5 H5B 109.2 . . ?
C6 C5 H5B 109.2 . . ?
H5A C5 H5B 107.9 . . ?
C5 C6 N9 112.8(4) . . ?
C5 C6 N7 112.8(4) . . ?
N9 C6 N7 108.7(4) . . ?
C5 C6 N8 110.3(4) . . ?
N9 C6 N8 106.1(4) . . ?
N7 C6 N8 105.8(4) . . ?
N10 C7 N12 120.9(4) . . ?
N10 C7 C8 109.4(4) . . ?
N12 C7 C8 129.6(4) . . ?
N11 C8 C7 109.8(4) . . ?
N11 C8 C2 121.3(5) . . ?
C7 C8 C2 128.7(4) . . ?
N12 C9 C10 113.2(4) . . ?
N12 C9 H9A 108.9 . . ?
C10 C9 H9A 108.9 . . ?
N12 C9 H9B 108.9 . . ?
C10 C9 H9B 108.9 . . ?
H9A C9 H9B 107.7 . . ?
N14 C10 N16 106.1(4) . . ?
N14 C10 N15 107.4(4) . . ?
N16 C10 N15 107.8(4) . . ?
N14 C10 C9 108.7(4) . . ?
N16 C10 C9 113.1(4) . . ?
N15 C10 C9 113.3(4) . . ?
C1 N1 O1 114.7(4) . . ?
C2 N2 O2 114.9(4) . . ?
C3 N3 O3 104.4(4) . . ?
C4 N4 O3 104.7(4) . . ?
C3 N5 N6 114.7(4) . . ?
C3 N5 C5 122.2(3) . . ?
N6 N5 C5 117.6(4) . . ?
O5 N6 O4 129.6(4) . . ?
O5 N6 N5 114.9(4) . . ?
O4 N6 N5 115.4(4) . . ?
O7 N7 O6 127.6(5) . . ?
O7 N7 C6 117.6(4) . . ?
O6 N7 C6 114.8(4) . . ?
O9 N8 O8 126.2(5) . . ?
O9 N8 C6 115.6(4) . . ?
O8 N8 C6 118.2(5) . . ?
O11 N9 O10 127.7(4) . . ?
O11 N9 C6 116.2(4) . . ?
O10 N9 C6 116.0(5) . . ?
C7 N10 O12 105.0(4) . . ?
C8 N11 O12 103.7(4) . . ?
C7 N12 N13 115.6(4) . . ?
C7 N12 C9 122.4(3) . . ?
N13 N12 C9 116.8(4) . . ?
O14 N13 O13 128.7(4) . . ?
O14 N13 N12 116.0(4) . . ?
O13 N13 N12 115.2(4) . . ?
O16 N14 O15 126.6(4) . . ?
O16 N14 C10 118.0(5) . . ?
O15 N14 C10 115.4(4) . . ?
O18 N15 O17 127.7(4) . . ?
O18 N15 C10 117.7(4) . . ?
O17 N15 C10 114.6(4) . . ?
O20 N16 O19 128.0(5) . . ?
O20 N16 C10 117.2(4) . . ?
O19 N16 C10 114.8(4) . . ?
C2 O1 N1 115.5(3) . . ?
C1 O2 N2 115.7(3) . . ?
N3 O3 N4 111.6(3) . . ?
N10 O12 N11 112.0(3) . . ?

_diffrn_measured_fraction_theta_max 0.985
_diffrn_reflns_theta_full        24.50
_diffrn_measured_fraction_theta_full 0.985
_refine_diff_density_max         0.335
_refine_diff_density_min         -0.331
_refine_diff_density_rms         0.075
####################################################################### 
# 
# 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 1477797'
_audit_update_record             
;
2016-05-03 deposited with the CCDC.
2017-09-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(H4 N), C6 N10 O8, H2 O'
_chemical_formula_sum            'C6 H10 N12 O9'
_chemical_formula_weight         394.26

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'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   'P-1   '
_symmetry_space_group_name_Hall  '-P 1   '

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.3127(7)
_cell_length_b                   8.4521(8)
_cell_length_c                   10.3335(9)
_cell_angle_alpha                84.769(4)
_cell_angle_beta                 83.777(3)
_cell_angle_gamma                85.505(3)
_cell_volume                     717.02(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    1442
_cell_measurement_theta_min      3.26
_cell_measurement_theta_max      25.03

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.11
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.826
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             404
_exptl_absorpt_coefficient_mu    0.168
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6869
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_process_details   'SADABS (Bruker, 2012)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  'TRIUMPH curved crystal monochromator'
_diffrn_measurement_device_type  'PHOTON100 CMOS detector'
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6929
_diffrn_reflns_av_R_equivalents  0.0596
_diffrn_reflns_av_sigmaI/netI    0.0684
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         3.01
_diffrn_reflns_theta_max         25.39
_reflns_number_total             2591
_reflns_number_gt                1532
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0438P)²+0.2624P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2591
_refine_ls_number_parameters     329
_refine_ls_number_restraints     316
_refine_ls_R_factor_all          0.1060
_refine_ls_R_factor_gt           0.0483
_refine_ls_wR_factor_ref         0.1120
_refine_ls_wR_factor_gt          0.0946
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_restrained_S_all      0.995
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C3 C 0.2230(3) 0.0692(3) 0.3267(2) 0.0198(7) Uani 1 1 d . A .
C4 C 0.3204(3) 0.1520(3) 0.4020(2) 0.0185(6) Uani 1 1 d D . .
C5 C 0.2747(3) 0.6195(3) 0.8761(2) 0.0177(7) Uani 1 1 d . A .
C6 C 0.1760(3) 0.5400(3) 0.7991(2) 0.0188(6) Uani 1 1 d D . .
N3 N 0.3210(3) -0.0112(3) 0.2435(2) 0.0316(7) Uani 1 1 d . . .
N4 N 0.4732(3) 0.1207(3) 0.3658(2) 0.0271(6) Uani 1 1 d . A .
N5 N 0.0562(3) 0.0840(3) 0.3483(2) 0.0222(6) Uani 1 1 d . . .
N6 N -0.0229(3) 0.0042(3) 0.2751(2) 0.0247(6) Uani 1 1 d . A .
N7 N 0.1768(3) 0.7046(3) 0.9556(2) 0.0251(6) Uani 1 1 d . . .
N8 N 0.0239(3) 0.5776(3) 0.8311(2) 0.0228(6) Uani 1 1 d . A .
N9 N 0.4411(3) 0.5979(3) 0.8588(2) 0.0208(6) Uani 1 1 d . . .
N10 N 0.5211(3) 0.6810(3) 0.9291(2) 0.0213(6) Uani 1 1 d . A .
N11 N 0.7258(3) 0.3829(3) 0.7440(2) 0.0254(6) Uani 1 1 d D . .
H11A H 0.6266(18) 0.430(3) 0.759(2) 0.038 Uiso 1 1 d D . .
H11B H 0.742(3) 0.359(3) 0.6609(14) 0.038 Uiso 1 1 d D . .
H11C H 0.799(2) 0.448(2) 0.759(2) 0.038 Uiso 1 1 d D . .
H11D H 0.734(3) 0.294(2) 0.7969(19) 0.038 Uiso 1 1 d D . .
N12 N 0.7528(3) 0.9330(3) 0.0436(2) 0.0281(6) Uani 1 1 d D . .
H12A H 0.731(3) 1.0297(18) 0.007(2) 0.042 Uiso 1 1 d D . .
H12B H 0.673(2) 0.870(2) 0.037(2) 0.042 Uiso 1 1 d D . .
H12C H 0.771(3) 0.937(3) 0.1257(14) 0.042 Uiso 1 1 d D . .
H12D H 0.842(2) 0.890(3) 0.000(2) 0.042 Uiso 1 1 d D . .
O3 O 0.4783(2) 0.0212(3) 0.26799(19) 0.0365(6) Uani 1 1 d . A .
O4 O -0.1746(2) 0.0173(3) 0.29559(18) 0.0310(5) Uani 1 1 d . . .
O5 O 0.0447(2) -0.0816(3) 0.18849(19) 0.0337(6) Uani 1 1 d . . .
O6 O 0.0198(2) 0.6792(2) 0.92766(18) 0.0270(5) Uani 1 1 d . A .
O7 O 0.6735(2) 0.6615(2) 0.91110(19) 0.0306(5) Uani 1 1 d . . .
O8 O 0.4552(2) 0.7744(2) 1.01001(18) 0.0269(5) Uani 1 1 d . . .
O9 O 0.2263(3) 0.7265(3) 0.5098(2) 0.0387(6) Uani 1 1 d D . .
H9A H 0.137(3) 0.768(4) 0.533(3) 0.046 Uiso 1 1 d D . .
H9B H 0.299(3) 0.760(4) 0.545(3) 0.046 Uiso 1 1 d D . .
O1 O 0.0918(12) 0.3763(12) 0.6572(9) 0.0261(17) Uani 0.420(9) 1 d PDU A 1
N1 N 0.1183(19) 0.302(4) 0.536(2) 0.024(2) Uani 0.420(9) 1 d PDU A 1
C1 C 0.2671(16) 0.267(2) 0.4987(15) 0.024(2) Uani 0.420(9) 1 d PDU A 1
O2 O 0.3993(7) 0.3359(11) 0.5314(8) 0.0308(17) Uani 0.420(9) 1 d PDU A 1
N2 N 0.3732(18) 0.4006(19) 0.6590(12) 0.028(2) Uani 0.420(9) 1 d PDU A 1
C2 C 0.2248(17) 0.432(2) 0.6996(16) 0.029(2) Uani 0.420(9) 1 d PDU A 1
O1' O 0.0979(9) 0.4265(8) 0.6178(7) 0.0297(14) Uani 0.580(9) 1 d PDU A 2
N1' N 0.1306(14) 0.308(3) 0.5258(16) 0.0238(18) Uani 0.580(9) 1 d PDU A 2
C1' C 0.2755(12) 0.2476(14) 0.5103(11) 0.0237(17) Uani 0.580(9) 1 d PDU A 2
O2' O 0.3961(5) 0.2538(8) 0.5881(6) 0.0302(14) Uani 0.580(9) 1 d PDU A 2
N2' N 0.3678(13) 0.3744(13) 0.6812(9) 0.0286(19) Uani 0.580(9) 1 d PDU A 2
C2' C 0.2224(13) 0.4373(16) 0.6932(12) 0.0281(17) Uani 0.580(9) 1 d PDU A 2


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C3 N3 1.316(3) . ?
C3 N5 1.378(3) . ?
C3 C4 1.440(4) . ?
C4 N4 1.298(3) . ?
C4 C1' 1.440(12) . ?
C4 C1 1.471(16) . ?
C5 N7 1.314(3) . ?
C5 N9 1.376(3) . ?
C5 C6 1.443(3) . ?
C6 N8 1.295(3) . ?
C6 C2 1.439(17) . ?
C6 C2' 1.459(13) . ?
N3 O3 1.411(3) . ?
N4 O3 1.367(3) . ?
N5 N6 1.315(3) . ?
N6 O4 1.253(3) . ?
N6 O5 1.261(3) . ?
N7 O6 1.403(3) . ?
N8 O6 1.370(3) . ?
N9 N10 1.317(3) . ?
N10 O8 1.255(3) . ?
N10 O7 1.260(3) . ?
N11 H11A 0.892(13) . ?
N11 H11B 0.895(13) . ?
N11 H11C 0.884(13) . ?
N11 H11D 0.890(13) . ?
N12 H12A 0.884(13) . ?
N12 H12B 0.892(14) . ?
N12 H12C 0.881(13) . ?
N12 H12D 0.893(14) . ?
O9 H9A 0.820(17) . ?
O9 H9B 0.818(17) . ?
O1 C2 1.365(11) . ?
O1 N1 1.440(11) . ?
N1 C1 1.275(12) . ?
C1 O2 1.368(11) . ?
O2 N2 1.461(10) . ?
N2 C2 1.276(11) . ?
O1' C2' 1.374(9) . ?
O1' N1' 1.436(10) . ?
N1' C1' 1.269(9) . ?
C1' O2' 1.358(9) . ?
O2' N2' 1.453(8) . ?
N2' C2' 1.280(9) . ?

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
N3 C3 N5 131.4(2) . . ?
N3 C3 C4 108.2(2) . . ?
N5 C3 C4 120.4(2) . . ?
N4 C4 C1' 118.9(4) . . ?
N4 C4 C3 109.9(2) . . ?
C1' C4 C3 131.0(4) . . ?
N4 C4 C1 121.2(5) . . ?
C1' C4 C1 8.2(10) . . ?
C3 C4 C1 128.6(5) . . ?
N7 C5 N9 131.6(2) . . ?
N7 C5 C6 107.8(2) . . ?
N9 C5 C6 120.6(2) . . ?
N8 C6 C2 120.5(6) . . ?
N8 C6 C5 110.1(2) . . ?
C2 C6 C5 129.5(6) . . ?
N8 C6 C2' 119.3(5) . . ?
C2 C6 C2' 3.0(11) . . ?
C5 C6 C2' 130.5(5) . . ?
C3 N3 O3 104.7(2) . . ?
C4 N4 O3 105.7(2) . . ?
N6 N5 C3 116.3(2) . . ?
O4 N6 O5 120.0(2) . . ?
O4 N6 N5 116.1(2) . . ?
O5 N6 N5 124.0(2) . . ?
C5 N7 O6 105.21(19) . . ?
C6 N8 O6 105.6(2) . . ?
N10 N9 C5 116.3(2) . . ?
O8 N10 O7 120.2(2) . . ?
O8 N10 N9 124.2(2) . . ?
O7 N10 N9 115.6(2) . . ?
H11A N11 H11B 109.3(15) . . ?
H11A N11 H11C 109.4(16) . . ?
H11B N11 H11C 110.1(15) . . ?
H11A N11 H11D 108.9(15) . . ?
H11B N11 H11D 109.4(15) . . ?
H11C N11 H11D 109.6(15) . . ?
H12A N12 H12B 111.0(16) . . ?
H12A N12 H12C 110.7(15) . . ?
H12B N12 H12C 111.0(16) . . ?
H12A N12 H12D 108.4(16) . . ?
H12B N12 H12D 106.5(15) . . ?
H12C N12 H12D 109.0(15) . . ?
N4 O3 N3 111.36(18) . . ?
N8 O6 N7 111.30(18) . . ?
H9A O9 H9B 113(3) . . ?
C2 O1 N1 116.2(10) . . ?
C1 N1 O1 114.1(13) . . ?
N1 C1 O2 127.4(14) . . ?
N1 C1 C4 123.1(11) . . ?
O2 C1 C4 109.3(10) . . ?
C1 O2 N2 113.5(9) . . ?
C2 N2 O2 114.6(12) . . ?
N2 C2 O1 127.3(15) . . ?
N2 C2 C6 122.4(12) . . ?
O1 C2 C6 110.3(11) . . ?
C2' O1' N1' 113.7(8) . . ?
C1' N1' O1' 116.5(10) . . ?
N1' C1' O2' 128.2(10) . . ?
N1' C1' C4 118.0(8) . . ?
O2' C1' C4 113.6(8) . . ?
C1' O2' N2' 115.0(7) . . ?
C2' N2' O2' 114.4(9) . . ?
N2' C2' O1' 129.6(11) . . ?
N2' C2' C6 118.1(9) . . ?
O1' C2' C6 112.3(8) . . ?

_diffrn_measured_fraction_theta_max 0.984
_diffrn_reflns_theta_full        25.39
_diffrn_measured_fraction_theta_full 0.984
_refine_diff_density_max         0.242
_refine_diff_density_min         -0.449
_refine_diff_density_rms         0.058
####################################################################### 
# 
# 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 1485750'
_audit_update_record             
;
2016-06-15 deposited with the CCDC.
2017-09-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(H4 N O), C6 N10 O8'
_chemical_formula_sum            'C6 H8 N12 O10'
_chemical_formula_weight         408.24

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

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P2(1)/c  '
_symmetry_space_group_name_Hall  '-P 2ybc  '

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

_cell_length_a                   12.4278(18)
_cell_length_b                   4.1913(5)
_cell_length_c                   14.8650(19)
_cell_angle_alpha                90.00
_cell_angle_beta                 113.668(5)
_cell_angle_gamma                90.00
_cell_volume                     709.17(16)
_cell_formula_units_Z            2
_cell_measurement_temperature    172(2)
_cell_measurement_reflns_used    760
_cell_measurement_theta_min      3.63
_cell_measurement_theta_max      24.76

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.09
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.912
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             416
_exptl_absorpt_coefficient_mu    0.179
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6899
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_process_details   'SADABS (Bruker, 2012)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      172(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  'TRIUMPH curved crystal monochromator'
_diffrn_measurement_device_type  'PHOTON100 CMOS detector'
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            3767
_diffrn_reflns_av_R_equivalents  0.0575
_diffrn_reflns_av_sigmaI/netI    0.0592
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.58
_diffrn_reflns_theta_max         25.36
_reflns_number_total             1268
_reflns_number_gt                862
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0283P)²+0.3064P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1268
_refine_ls_number_parameters     138
_refine_ls_number_restraints     10
_refine_ls_R_factor_all          0.0782
_refine_ls_R_factor_gt           0.0398
_refine_ls_wR_factor_ref         0.0849
_refine_ls_wR_factor_gt          0.0743
_refine_ls_goodness_of_fit_ref   1.046
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.0646(2) 1.0356(6) 0.09244(19) 0.0181(6) Uani 1 1 d . . .
C2 C 0.2283(2) 0.9474(6) 0.27008(18) 0.0156(6) Uani 1 1 d . . .
C3 C 0.1252(2) 1.0915(6) 0.19753(18) 0.0166(6) Uani 1 1 d . . .
N1 N 0.10803(18) 0.8494(5) 0.04856(15) 0.0233(5) Uani 1 1 d . . .
N2 N 0.24309(18) 1.0633(5) 0.35650(15) 0.0212(5) Uani 1 1 d . . .
N3 N 0.08041(17) 1.2947(5) 0.23986(15) 0.0208(5) Uani 1 1 d . . .
N4 N 0.29398(17) 0.7280(5) 0.24428(14) 0.0164(5) Uani 1 1 d . . .
N5 N 0.38466(17) 0.6037(5) 0.31816(15) 0.0180(5) Uani 1 1 d . . .
N6 N 0.34839(17) 0.6193(5) 0.06311(14) 0.0183(5) Uani 1 1 d D . .
H6B H 0.3345(17) 0.598(5) -0.0038(12) 0.022 Uiso 1 1 d D . .
H6C H 0.2865(15) 0.735(4) 0.0688(14) 0.022 Uiso 1 1 d D . .
H6D H 0.4207(15) 0.711(4) 0.0996(14) 0.022 Uiso 1 1 d D . .
O1 O -0.0481(3) 1.1464(10) 0.0557(3) 0.0203(12) Uiso 0.50 1 d P . .
O2 O 0.0281(4) 0.7544(10) -0.0519(3) 0.0193(11) Uiso 0.50 1 d P . .
O3 O 0.15094(15) 1.2819(4) 0.33754(13) 0.0245(5) Uani 1 1 d . . .
O4 O 0.41508(15) 0.6725(5) 0.40557(12) 0.0286(5) Uani 1 1 d . . .
O5 O 0.44152(14) 0.3931(4) 0.29240(12) 0.0192(4) Uani 1 1 d . . .
O6 O 0.34493(17) 0.3077(4) 0.09814(13) 0.0264(5) Uani 1 1 d D . .
H6A H 0.371(2) 0.334(7) 0.1602(13) 0.032 Uiso 1 1 d D . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.269(3) . ?
C1 O1 1.364(4) . ?
C1 O2 1.381(4) 3_575 ?
C1 C3 1.455(3) . ?
C2 N2 1.316(3) . ?
C2 N4 1.382(3) . ?
C2 C3 1.436(3) . ?
C3 N3 1.309(3) . ?
N1 O1 1.424(4) 3_575 ?
N1 O2 1.478(4) . ?
N2 O3 1.404(3) . ?
N3 O3 1.363(3) . ?
N4 N5 1.324(3) . ?
N5 O4 1.233(2) . ?
N5 O5 1.282(2) . ?
N6 O6 1.413(3) . ?
N6 H6B 0.942(15) . ?
N6 H6C 0.940(15) . ?
N6 H6D 0.927(16) . ?
O1 O2 0.499(5) 3_575 ?
O1 N1 1.424(4) 3_575 ?
O2 O1 0.499(5) 3_575 ?
O2 C1 1.381(4) 3_575 ?
O6 H6A 0.853(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 O1 125.7(3) . . ?
N1 C1 O2 128.3(3) . 3_575 ?
O1 C1 O2 20.9(2) . 3_575 ?
N1 C1 C3 120.5(2) . . ?
O1 C1 C3 112.4(3) . . ?
O2 C1 C3 110.4(3) 3_575 . ?
N2 C2 N4 130.6(2) . . ?
N2 C2 C3 108.1(2) . . ?
N4 C2 C3 121.3(2) . . ?
N3 C3 C2 109.7(2) . . ?
N3 C3 C1 118.9(2) . . ?
C2 C3 C1 131.3(2) . . ?
C1 N1 O1 114.0(2) . 3_575 ?
C1 N1 O2 115.6(2) . . ?
O1 N1 O2 19.7(2) 3_575 . ?
C2 N2 O3 105.20(19) . . ?
C3 N3 O3 105.71(19) . . ?
N5 N4 C2 115.61(19) . . ?
O4 N5 O5 120.2(2) . . ?
O4 N5 N4 125.5(2) . . ?
O5 N5 N4 114.26(19) . . ?
O6 N6 H6B 106.4(12) . . ?
O6 N6 H6C 107.1(12) . . ?
H6B N6 H6C 109.5(14) . . ?
O6 N6 H6D 109.5(12) . . ?
H6B N6 H6D 112.4(15) . . ?
H6C N6 H6D 111.7(15) . . ?
O2 O1 C1 81.4(8) 3_575 . ?
O2 O1 N1 86.2(8) 3_575 3_575 ?
C1 O1 N1 116.4(3) . 3_575 ?
O1 O2 C1 77.6(8) 3_575 3_575 ?
O1 O2 N1 74.1(8) 3_575 . ?
C1 O2 N1 112.0(3) 3_575 . ?
N3 O3 N2 111.32(17) . . ?
N6 O6 H6A 102.8(19) . . ?

_diffrn_measured_fraction_theta_max 0.983
_diffrn_reflns_theta_full        25.36
_diffrn_measured_fraction_theta_full 0.983
_refine_diff_density_max         0.245
_refine_diff_density_min         -0.263
_refine_diff_density_rms         0.059
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1_CCDC3
_database_code_depnum_ccdc_archive 'CCDC 1477800'
_audit_update_record             
;
2016-05-03 deposited with the CCDC.
2017-09-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C H7 N4), C6 N10 O8'
_chemical_formula_sum            'C8 H14 N18 O8'
_chemical_formula_weight         490.37

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'C2/c  '
_symmetry_space_group_name_Hall  '-C 2yc  '

loop_
_symmetry_equiv_pos_as_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                   21.716(2)
_cell_length_b                   6.6158(6)
_cell_length_c                   16.972(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 129.579(3)
_cell_angle_gamma                90.00
_cell_volume                     1879.4(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    1323
_cell_measurement_theta_min      3.11
_cell_measurement_theta_max      24.57

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.19
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.733
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1008
_exptl_absorpt_coefficient_mu    0.152
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6587
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_process_details   'SADABS (Bruker, 2012)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  'TRIUMPH curved crystal monochromator'
_diffrn_measurement_device_type  'PHOTON100 CMOS detector'
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5715
_diffrn_reflns_av_R_equivalents  0.0559
_diffrn_reflns_av_sigmaI/netI    0.0513
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         3.11
_diffrn_reflns_theta_max         25.38
_reflns_number_total             1701
_reflns_number_gt                1187
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0426P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1701
_refine_ls_number_parameters     175
_refine_ls_number_restraints     16
_refine_ls_R_factor_all          0.0742
_refine_ls_R_factor_gt           0.0392
_refine_ls_wR_factor_ref         0.0899
_refine_ls_wR_factor_gt          0.0783
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_restrained_S_all      1.023
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C -0.02513(12) 0.5858(3) 0.15941(16) 0.0167(5) Uani 1 1 d . . .
C2 C 0.01397(13) 0.7460(3) 0.05602(17) 0.0187(5) Uani 1 1 d . . .
C3 C -0.03983(12) 0.6472(3) 0.06567(16) 0.0169(5) Uani 1 1 d . . .
C4 C 0.18019(13) 0.9371(3) -0.00724(17) 0.0183(5) Uani 1 1 d . . .
N1 N -0.08043(11) 0.5937(2) 0.16525(14) 0.0192(4) Uani 1 1 d . . .
N2 N -0.02221(11) 0.7625(2) -0.04156(14) 0.0245(5) Uani 1 1 d . . .
N3 N -0.10724(11) 0.6070(3) -0.02428(15) 0.0246(5) Uani 1 1 d . . .
N4 N 0.09324(11) 0.8049(3) 0.12602(14) 0.0211(4) Uani 1 1 d . . .
N5 N 0.11083(11) 0.9029(3) 0.20576(14) 0.0208(4) Uani 1 1 d . . .
N6 N 0.23357(12) 1.0011(3) -0.01513(16) 0.0231(5) Uani 1 1 d D . .
H6A H 0.2194(13) 1.017(3) -0.0772(12) 0.028 Uiso 1 1 d D . .
H6B H 0.2830(10) 1.017(3) 0.0412(13) 0.028 Uiso 1 1 d D . .
N7 N 0.20071(11) 0.9073(3) 0.08432(15) 0.0247(5) Uani 1 1 d D . .
H7 H 0.1660(12) 0.863(3) 0.0904(17) 0.030 Uiso 1 1 d D . .
N8 N 0.28055(13) 0.9412(3) 0.17177(17) 0.0349(5) Uani 1 1 d D . .
H8A H 0.2782(15) 1.038(3) 0.2059(17) 0.042 Uiso 1 1 d D . .
H8B H 0.2984(14) 0.819(3) 0.2036(17) 0.042 Uiso 1 1 d D . .
N9 N 0.10564(12) 0.8975(3) -0.09077(15) 0.0245(5) Uani 1 1 d D . .
H9A H 0.0917(14) 0.936(3) -0.1493(19) 0.029 Uiso 1 1 d . . .
H9B H 0.0693(12) 0.875(3) -0.0844(18) 0.029 Uiso 1 1 d D . .
O1 O -0.05091(9) 0.5214(2) 0.26507(11) 0.0217(4) Uani 1 1 d . . .
O2 O -0.09786(9) 0.6778(2) -0.09283(12) 0.0287(4) Uani 1 1 d . . .
O3 O 0.05877(9) 0.9456(2) 0.21443(11) 0.0222(4) Uani 1 1 d . . .
O4 O 0.18218(9) 0.9560(2) 0.27305(12) 0.0304(4) 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 1.267(3) . ?
C1 O1 1.362(2) 2 ?
C1 C3 1.467(3) . ?
C2 N2 1.309(3) . ?
C2 N4 1.386(3) . ?
C2 C3 1.436(3) . ?
C3 N3 1.302(3) . ?
C4 N6 1.319(3) . ?
C4 N7 1.330(3) . ?
C4 N9 1.332(3) . ?
N1 O1 1.458(2) . ?
N2 O2 1.396(2) . ?
N3 O2 1.384(2) . ?
N4 N5 1.319(2) . ?
N5 O4 1.254(2) . ?
N5 O3 1.262(2) . ?
N6 H6A 0.897(14) . ?
N6 H6B 0.877(15) . ?
N7 N8 1.407(3) . ?
N7 H7 0.875(15) . ?
N8 H8A 0.886(14) . ?
N8 H8B 0.910(15) . ?
N9 H9A 0.87(2) . ?
N9 H9B 0.876(15) . ?
O1 C1 1.362(2) 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 O1 125.5(2) . 2 ?
N1 C1 C3 120.7(2) . . ?
O1 C1 C3 113.76(17) 2 . ?
N2 C2 N4 118.52(18) . . ?
N2 C2 C3 107.82(19) . . ?
N4 C2 C3 133.4(2) . . ?
N3 C3 C2 110.35(19) . . ?
N3 C3 C1 121.35(19) . . ?
C2 C3 C1 128.25(19) . . ?
N6 C4 N7 120.3(2) . . ?
N6 C4 N9 120.4(2) . . ?
N7 C4 N9 119.3(2) . . ?
C1 N1 O1 109.89(17) . . ?
C2 N2 O2 105.94(16) . . ?
C3 N3 O2 104.99(17) . . ?
N5 N4 C2 114.04(17) . . ?
O4 N5 O3 120.65(18) . . ?
O4 N5 N4 117.01(17) . . ?
O3 N5 N4 122.33(18) . . ?
C4 N6 H6A 119.5(14) . . ?
C4 N6 H6B 118.2(15) . . ?
H6A N6 H6B 122(2) . . ?
C4 N7 N8 118.63(19) . . ?
C4 N7 H7 121.0(15) . . ?
N8 N7 H7 120.3(15) . . ?
N7 N8 H8A 105.0(17) . . ?
N7 N8 H8B 104.9(16) . . ?
H8A N8 H8B 116(2) . . ?
C4 N9 H9A 117.4(16) . . ?
C4 N9 H9B 118.9(16) . . ?
H9A N9 H9B 120(2) . . ?
C1 O1 N1 111.27(14) 2 . ?
N3 O2 N2 110.90(15) . . ?

_diffrn_measured_fraction_theta_max 0.985
_diffrn_reflns_theta_full        25.38
_diffrn_measured_fraction_theta_full 0.985
_refine_diff_density_max         0.215
_refine_diff_density_min         -0.227
_refine_diff_density_rms         0.050
####################################################################### 
# 
# 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 1477801'
_audit_update_record             
;
2016-05-03 deposited with the CCDC.
2017-09-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C H5 N6), C6 N10 O8'
_chemical_formula_sum            'C8 H10 N22 O8'
_chemical_formula_weight         542.38

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P2(1)/n  '
_symmetry_space_group_name_Hall  '-P 2yn  '

loop_
_symmetry_equiv_pos_as_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                   13.3360(14)
_cell_length_b                   4.4928(5)
_cell_length_c                   16.633(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 96.477(4)
_cell_angle_gamma                90.00
_cell_volume                     990.2(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    971
_cell_measurement_theta_min      3.72
_cell_measurement_theta_max      24.91

_exptl_crystal_description       plate
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.07
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.819
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             552
_exptl_absorpt_coefficient_mu    0.159
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6797
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_process_details   'SADABS (Bruker, 2012)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  'TRIUMPH curved crystal monochromator'
_diffrn_measurement_device_type  'PHOTON100 CMOS detector'
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5412
_diffrn_reflns_av_R_equivalents  0.0669
_diffrn_reflns_av_sigmaI/netI    0.0697
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         3.07
_diffrn_reflns_theta_max         25.44
_reflns_number_total             1814
_reflns_number_gt                1170
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0434P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1814
_refine_ls_number_parameters     187
_refine_ls_number_restraints     11
_refine_ls_R_factor_all          0.0959
_refine_ls_R_factor_gt           0.0433
_refine_ls_wR_factor_ref         0.1008
_refine_ls_wR_factor_gt          0.0845
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_restrained_S_all      1.032
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.53436(19) 0.4570(6) 0.07454(14) 0.0165(6) Uani 1 1 d . . .
C2 C 0.55343(18) 0.4853(6) 0.23377(14) 0.0184(6) Uani 1 1 d . . .
C3 C 0.57804(19) 0.3793(6) 0.15679(15) 0.0170(6) Uani 1 1 d . . .
C4 C 0.68037(19) 0.5701(6) 0.52087(16) 0.0199(6) Uani 1 1 d . . .
N1 N 0.52378(16) 0.3197(5) -0.06435(12) 0.0203(5) Uani 1 1 d . . .
N2 N 0.61291(16) 0.3517(5) 0.29091(12) 0.0215(5) Uani 1 1 d . . .
N3 N 0.65086(16) 0.1848(5) 0.16798(13) 0.0230(6) Uani 1 1 d . . .
N4 N 0.47458(16) 0.6824(5) 0.23900(12) 0.0241(6) Uani 1 1 d . . .
N5 N 0.46168(17) 0.7774(5) 0.31206(13) 0.0251(6) Uani 1 1 d . . .
N6 N 0.75514(15) 0.4711(5) 0.57432(13) 0.0218(6) Uani 1 1 d . . .
N7 N 0.80918(16) 0.2571(5) 0.53961(14) 0.0268(6) Uani 1 1 d . . .
N8 N 0.76975(17) 0.2252(5) 0.46665(14) 0.0267(6) Uani 1 1 d . . .
N9 N 0.69013(16) 0.4156(5) 0.45388(13) 0.0211(6) Uani 1 1 d D . .
H9 H 0.6580(17) 0.427(6) 0.4029(11) 0.025 Uiso 1 1 d D . .
N10 N 0.77620(18) 0.5729(6) 0.65352(14) 0.0307(6) Uani 1 1 d D . .
H10A H 0.8370(15) 0.665(6) 0.6570(17) 0.037 Uiso 1 1 d D . .
H10B H 0.7661(19) 0.414(5) 0.6867(15) 0.037 Uiso 1 1 d D . .
N11 N 0.61312(17) 0.7738(6) 0.53339(14) 0.0254(6) Uani 1 1 d D . .
H11A H 0.6159(19) 0.862(6) 0.5828(11) 0.031 Uiso 1 1 d D . .
H11B H 0.5694(17) 0.811(6) 0.4900(12) 0.031 Uiso 1 1 d D . .
O1 O 0.56377(14) 0.2658(4) 0.01861(10) 0.0243(5) Uani 1 1 d . . .
O2 O 0.67395(13) 0.1634(4) 0.25048(10) 0.0253(5) Uani 1 1 d . . .
O3 O 0.38562(14) 0.9413(5) 0.31652(11) 0.0377(6) Uani 1 1 d . . .
O4 O 0.51949(14) 0.7159(5) 0.37456(11) 0.0325(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 1.268(3) 3_665 ?
C1 O1 1.356(3) . ?
C1 C3 1.467(3) . ?
C2 N2 1.312(3) . ?
C2 N4 1.385(3) . ?
C2 C3 1.438(3) . ?
C3 N3 1.304(3) . ?
C4 N11 1.314(3) . ?
C4 N9 1.332(3) . ?
C4 N6 1.335(3) . ?
N1 C1 1.268(3) 3_665 ?
N1 O1 1.442(3) . ?
N2 O2 1.398(3) . ?
N3 O2 1.375(3) . ?
N4 N5 1.317(3) . ?
N5 O4 1.253(3) . ?
N5 O3 1.262(3) . ?
N6 N7 1.368(3) . ?
N6 N10 1.393(3) . ?
N7 N8 1.275(3) . ?
N8 N9 1.362(3) . ?
N9 H9 0.907(17) . ?
N10 H10A 0.907(17) . ?
N10 H10B 0.922(17) . ?
N11 H11A 0.909(17) . ?
N11 H11B 0.892(16) . ?

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 O1 129.0(2) 3_665 . ?
N1 C1 C3 119.0(2) 3_665 . ?
O1 C1 C3 112.0(2) . . ?
N2 C2 N4 130.4(2) . . ?
N2 C2 C3 108.3(2) . . ?
N4 C2 C3 121.3(2) . . ?
N3 C3 C2 109.6(2) . . ?
N3 C3 C1 120.2(2) . . ?
C2 C3 C1 130.1(2) . . ?
N11 C4 N9 128.9(2) . . ?
N11 C4 N6 126.7(2) . . ?
N9 C4 N6 104.3(2) . . ?
C1 N1 O1 114.5(2) 3_665 . ?
C2 N2 O2 105.40(19) . . ?
C3 N3 O2 105.6(2) . . ?
N5 N4 C2 116.4(2) . . ?
O4 N5 O3 120.2(2) . . ?
O4 N5 N4 124.2(2) . . ?
O3 N5 N4 115.6(2) . . ?
C4 N6 N7 110.0(2) . . ?
C4 N6 N10 125.2(2) . . ?
N7 N6 N10 124.8(2) . . ?
N8 N7 N6 107.5(2) . . ?
N7 N8 N9 108.0(2) . . ?
C4 N9 N8 110.2(2) . . ?
C4 N9 H9 132.2(17) . . ?
N8 N9 H9 117.4(17) . . ?
N6 N10 H10A 107.1(19) . . ?
N6 N10 H10B 106.5(18) . . ?
H10A N10 H10B 120(2) . . ?
C4 N11 H11A 119.1(16) . . ?
C4 N11 H11B 113.4(18) . . ?
H11A N11 H11B 127(2) . . ?
C1 O1 N1 116.47(18) . . ?
N3 O2 N2 111.13(17) . . ?

_diffrn_measured_fraction_theta_max 0.985
_diffrn_reflns_theta_full        25.44
_diffrn_measured_fraction_theta_full 0.985
_refine_diff_density_max         0.224
_refine_diff_density_min         -0.257
_refine_diff_density_rms         0.059
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1_CCDC5
_database_code_depnum_ccdc_archive 'CCDC 1477793'
_audit_update_record             
;
2016-05-03 deposited with the CCDC.
2017-09-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 H2 N10 O8, 0.33(C H2 Cl2)'
_chemical_formula_sum            'C6.33 H2.67 Cl0.67 N10 O8'
_chemical_formula_weight         370.48

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Trigonal
_symmetry_space_group_name_H-M   'R-3   '
_symmetry_space_group_name_Hall  '-R 3   '

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'-x+2/3, -y+1/3, -z+1/3'
'y+2/3, -x+y+1/3, -z+1/3'
'x-y+2/3, x+1/3, -z+1/3'
'-x+1/3, -y+2/3, -z+2/3'
'y+1/3, -x+y+2/3, -z+2/3'
'x-y+1/3, x+2/3, -z+2/3'

_cell_length_a                   24.9941(19)
_cell_length_b                   24.9941(19)
_cell_length_c                   5.1946(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                120.00
_cell_volume                     2810.3(5)
_cell_formula_units_Z            9
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    500
_cell_measurement_theta_min      4.31
_cell_measurement_theta_max      24.24

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.07
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.970
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1674
_exptl_absorpt_coefficient_mu    0.315
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6560
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_process_details   'SADABS (Bruker, 2012)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  'TRIUMPH curved crystal monochromator'
_diffrn_measurement_device_type  'PHOTON100 CMOS detector'
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            2818
_diffrn_reflns_av_R_equivalents  0.0695
_diffrn_reflns_av_sigmaI/netI    0.0817
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_limit_l_max       4
_diffrn_reflns_theta_min         3.26
_diffrn_reflns_theta_max         25.32
_reflns_number_total             1121
_reflns_number_gt                676
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0580P)²+2.0327P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1121
_refine_ls_number_parameters     124
_refine_ls_number_restraints     5
_refine_ls_R_factor_all          0.1127
_refine_ls_R_factor_gt           0.0503
_refine_ls_wR_factor_ref         0.1291
_refine_ls_wR_factor_gt          0.1073
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_restrained_S_all      1.027
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C4 C 0.3331(12) 0.6769(15) 0.376(4) 0.074(6) Uiso 0.17 1 d PDU . .
H4A H 0.3490 0.7204 0.3521 0.089 Uiso 0.17 1 d PR . .
H4B H 0.3257 0.6672 0.5557 0.089 Uiso 0.17 1 d PR . .
Cl1 Cl 0.3821(5) 0.6545(6) 0.2558(18) 0.059(2) Uiso 0.17 1 d PDU . .
Cl2 Cl 0.2669(6) 0.6356(8) 0.199(3) 0.106(4) Uiso 0.17 1 d PDU . .
C1 C 0.63970(15) 0.78177(15) -0.0453(6) 0.0212(8) Uani 1 1 d . . .
C2 C 0.54978(16) 0.67264(15) 0.0904(7) 0.0228(8) Uani 1 1 d . . .
C3 C 0.61092(15) 0.72512(15) 0.1071(6) 0.0205(8) Uani 1 1 d . . .
N1 N 0.61131(12) 0.78248(12) -0.2463(6) 0.0242(7) Uani 1 1 d . . .
N2 N 0.54150(14) 0.63362(13) 0.2731(6) 0.0295(8) Uani 1 1 d . . .
N3 N 0.63950(14) 0.71703(13) 0.2982(6) 0.0287(8) Uani 1 1 d . . .
N4 N 0.50825(14) 0.66576(13) -0.0980(6) 0.0286(8) Uani 1 1 d . . .
H4 H 0.5139(16) 0.6949(17) -0.206(7) 0.034 Uiso 1 1 d . . .
N5 N 0.45129(14) 0.61326(13) -0.1290(7) 0.0332(8) Uani 1 1 d . . .
O1 O 0.64000(11) 0.83988(10) -0.3881(4) 0.0328(7) Uani 1 1 d . . .
O2 O 0.59815(12) 0.66148(11) 0.4043(5) 0.0325(7) Uani 1 1 d . . .
O3 O 0.43511(12) 0.57391(12) 0.0377(6) 0.0450(8) Uani 1 1 d . . .
O4 O 0.42363(12) 0.61183(11) -0.3229(6) 0.0432(8) 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
C4 C4 0.45(5) 2_665 ?
C4 C4 0.45(5) 3_565 ?
C4 Cl1 1.30(3) 2_665 ?
C4 Cl2 1.54(4) 3_565 ?
C4 Cl1 1.62(3) 3_565 ?
C4 Cl1 1.699(19) . ?
C4 Cl2 1.71(2) . ?
C4 Cl2 1.74(3) 14_455 ?
C4 Cl2 1.91(2) 2_665 ?
C4 Cl2 1.94(3) 13_565 ?
C4 Cl1 1.98(2) 13_565 ?
C4 Cl1 2.05(3) 15 ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
Cl1 Cl2 0.602(17) 2_665 ?
Cl1 Cl2 1.132(15) 13_565 ?
Cl1 C4 1.30(3) 3_565 ?
Cl1 C4 1.62(3) 2_665 ?
Cl1 Cl1 1.675(14) 14_455 ?
Cl1 Cl1 1.675(14) 15 ?
Cl1 Cl2 1.949(14) 15 ?
Cl1 C4 1.98(2) 13_565 ?
Cl1 C4 2.05(3) 14_455 ?
Cl1 Cl2 2.171(12) 3_565 ?
Cl1 Cl1 2.417(16) 3_565 ?
Cl2 Cl1 0.602(16) 3_565 ?
Cl2 Cl1 1.132(15) 13_565 ?
Cl2 Cl2 1.476(16) 15 ?
Cl2 Cl2 1.476(16) 14_455 ?
Cl2 C4 1.54(4) 2_665 ?
Cl2 C4 1.74(3) 15 ?
Cl2 C4 1.91(2) 3_565 ?
Cl2 C4 1.94(3) 13_565 ?
Cl2 Cl1 1.949(14) 14_455 ?
Cl2 C4 2.08(3) 14_455 ?
Cl2 Cl1 2.171(12) 2_665 ?
C1 N1 1.267(4) . ?
C1 O1 1.351(4) 16_664 ?
C1 C3 1.460(5) . ?
C2 N2 1.301(4) . ?
C2 N4 1.373(4) . ?
C2 C3 1.435(5) . ?
C3 N3 1.296(4) . ?
N1 O1 1.444(3) . ?
N2 O2 1.403(4) . ?
N3 O2 1.366(3) . ?
N4 N5 1.381(4) . ?
N4 H4 0.87(4) . ?
N5 O4 1.212(4) . ?
N5 O3 1.218(4) . ?
O1 C1 1.351(4) 16_664 ?

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
C4 C4 C4 60.00(5) 2_665 3_565 ?
C4 C4 Cl1 148(3) 2_665 2_665 ?
C4 C4 Cl1 129(6) 3_565 2_665 ?
C4 C4 Cl2 142.1(14) 2_665 3_565 ?
C4 C4 Cl2 106(5) 3_565 3_565 ?
Cl1 C4 Cl2 22.6(9) 2_665 3_565 ?
C4 C4 Cl1 39(5) 2_665 3_565 ?
C4 C4 Cl1 92(6) 3_565 3_565 ?
Cl1 C4 Cl1 111.1(14) 2_665 3_565 ?
Cl2 C4 Cl1 116.9(13) 3_565 3_565 ?
C4 C4 Cl1 72(5) 2_665 . ?
C4 C4 Cl1 24(2) 3_565 . ?
Cl1 C4 Cl1 106.5(18) 2_665 . ?
Cl2 C4 Cl1 84.2(12) 3_565 . ?
Cl1 C4 Cl1 93.4(13) 3_565 . ?
C4 C4 Cl2 59(5) 2_665 . ?
C4 C4 Cl2 109(5) 3_565 . ?
Cl1 C4 Cl2 91.0(13) 2_665 . ?
Cl2 C4 Cl2 99.9(15) 3_565 . ?
Cl1 C4 Cl2 20.6(6) 3_565 . ?
Cl1 C4 Cl2 104.0(12) . . ?
C4 C4 Cl2 109(5) 2_665 14_455 ?
C4 C4 Cl2 134.0(8) 3_565 14_455 ?
Cl1 C4 Cl2 40.5(8) 2_665 14_455 ?
Cl2 C4 Cl2 53.1(9) 3_565 14_455 ?
Cl1 C4 Cl2 70.7(10) 3_565 14_455 ?
Cl1 C4 Cl2 112.1(13) . 14_455 ?
Cl2 C4 Cl2 50.5(6) . 14_455 ?
C4 C4 Cl2 58(4) 2_665 2_665 ?
C4 C4 Cl2 29.6(15) 3_565 2_665 ?
Cl1 C4 Cl2 112.3(16) 2_665 2_665 ?
Cl2 C4 Cl2 91.9(13) 3_565 2_665 ?
Cl1 C4 Cl2 75.4(11) 3_565 2_665 ?
Cl1 C4 Cl2 18.0(6) . 2_665 ?
Cl2 C4 Cl2 86.7(12) . 2_665 ?
Cl2 C4 Cl2 104.8(11) 14_455 2_665 ?
C4 C4 Cl2 103(4) 2_665 13_565 ?
C4 C4 Cl2 58(4) 3_565 13_565 ?
Cl1 C4 Cl2 71.0(14) 2_665 13_565 ?
Cl2 C4 Cl2 48.7(8) 3_565 13_565 ?
Cl1 C4 Cl2 106.5(12) 3_565 13_565 ?
Cl1 C4 Cl2 35.5(6) . 13_565 ?
Cl2 C4 Cl2 104.8(11) . 13_565 ?
Cl2 C4 Cl2 85.1(13) 14_455 13_565 ?
Cl2 C4 Cl2 45.1(5) 2_665 13_565 ?
C4 C4 Cl1 92(4) 2_665 13_565 ?
C4 C4 Cl1 124(2) 3_565 13_565 ?
Cl1 C4 Cl1 56.9(8) 2_665 13_565 ?
Cl2 C4 Cl1 65.9(11) 3_565 13_565 ?
Cl1 C4 Cl1 54.3(6) 3_565 13_565 ?
Cl1 C4 Cl1 105.8(10) . 13_565 ?
Cl2 C4 Cl1 34.7(7) . 13_565 ?
Cl2 C4 Cl1 17.1(6) 14_455 13_565 ?
Cl2 C4 Cl1 94.3(9) 2_665 13_565 ?
Cl2 C4 Cl1 86.7(10) 13_565 13_565 ?
C4 C4 Cl1 113(3) 2_665 15 ?
C4 C4 Cl1 75(4) 3_565 15 ?
Cl1 C4 Cl1 54.7(10) 2_665 15 ?
Cl2 C4 Cl1 33.1(7) 3_565 15 ?
Cl1 C4 Cl1 106.0(10) 3_565 15 ?
Cl1 C4 Cl1 52.1(7) . 15 ?
Cl2 C4 Cl1 98.4(11) . 15 ?
Cl2 C4 Cl1 69.4(10) 14_455 15 ?
Cl2 C4 Cl1 58.9(8) 2_665 15 ?
Cl2 C4 Cl1 17.1(5) 13_565 15 ?
Cl1 C4 Cl1 73.7(9) 13_565 15 ?
C4 C4 H4A 169.4 2_665 . ?
C4 C4 H4A 127.3 3_565 . ?
Cl1 C4 H4A 22.4 2_665 . ?
Cl2 C4 H4A 33.5 3_565 . ?
Cl1 C4 H4A 130.6 3_565 . ?
Cl1 C4 H4A 111.5 . . ?
Cl2 C4 H4A 110.0 . . ?
Cl2 C4 H4A 60.6 14_455 . ?
Cl2 C4 H4A 123.5 2_665 . ?
Cl2 C4 H4A 78.4 13_565 . ?
Cl1 C4 H4A 77.6 13_565 . ?
Cl1 C4 H4A 65.3 15 . ?
C4 C4 H4B 77.5 2_665 . ?
C4 C4 H4B 87.3 3_565 . ?
Cl1 C4 H4B 129.3 2_665 . ?
Cl2 C4 H4B 139.8 3_565 . ?
Cl1 C4 H4B 99.8 3_565 . ?
Cl1 C4 H4B 110.7 . . ?
Cl2 C4 H4B 111.4 . . ?
Cl2 C4 H4B 136.6 14_455 . ?
Cl2 C4 H4B 113.8 2_665 . ?
Cl2 C4 H4B 136.7 13_565 . ?
Cl1 C4 H4B 136.4 13_565 . ?
Cl1 C4 H4B 149.2 15 . ?
H4A C4 H4B 109.2 . . ?
Cl2 Cl1 Cl2 113(2) 2_665 13_565 ?
Cl2 Cl1 C4 101(2) 2_665 3_565 ?
Cl2 Cl1 C4 91.2(14) 13_565 3_565 ?
Cl2 Cl1 C4 89(2) 2_665 2_665 ?
Cl2 Cl1 C4 96.6(14) 13_565 2_665 ?
C4 Cl1 C4 12.5(14) 3_565 2_665 ?
Cl2 Cl1 Cl1 21(2) 2_665 14_455 ?
Cl2 Cl1 Cl1 99.6(10) 13_565 14_455 ?
C4 Cl1 Cl1 85.9(10) 3_565 14_455 ?
C4 Cl1 Cl1 74.0(10) 2_665 14_455 ?
Cl2 Cl1 Cl1 108(2) 2_665 15 ?
Cl2 Cl1 Cl1 10.9(10) 13_565 15 ?
C4 Cl1 Cl1 82.5(10) 3_565 15 ?
C4 Cl1 Cl1 86.7(8) 2_665 15 ?
Cl1 Cl1 Cl1 92.4(7) 14_455 15 ?
Cl2 Cl1 C4 101.3(18) 2_665 . ?
Cl2 Cl1 C4 83.7(15) 13_565 . ?
C4 Cl1 C4 8.1(14) 3_565 . ?
C4 Cl1 C4 15.3(17) 2_665 . ?
Cl1 Cl1 C4 84.3(8) 14_455 . ?
Cl1 Cl1 C4 74.7(11) 15 . ?
Cl2 Cl1 Cl2 32.4(14) 2_665 15 ?
Cl2 Cl1 Cl2 104.8(13) 13_565 15 ?
C4 Cl1 Cl2 69.8(13) 3_565 15 ?
C4 Cl1 Cl2 57.6(12) 2_665 15 ?
Cl1 Cl1 Cl2 17.1(6) 14_455 15 ?
Cl1 Cl1 Cl2 95.5(6) 15 15 ?
C4 Cl1 Cl2 69.1(10) . 15 ?
Cl2 Cl1 C4 58(2) 2_665 13_565 ?
Cl2 Cl1 C4 59.6(11) 13_565 13_565 ?
C4 Cl1 C4 80.6(14) 3_565 13_565 ?
C4 Cl1 C4 74.0(15) 2_665 13_565 ?
Cl1 Cl1 C4 40.6(10) 14_455 13_565 ?
Cl1 Cl1 C4 51.8(11) 15 13_565 ?
C4 Cl1 C4 74.2(10) . 13_565 ?
Cl2 Cl1 C4 46.0(12) 15 13_565 ?
Cl2 Cl1 C4 71(2) 2_665 14_455 ?
Cl2 Cl1 C4 47.8(12) 13_565 14_455 ?
C4 Cl1 C4 78.1(14) 3_565 14_455 ?
C4 Cl1 C4 74.0(10) 2_665 14_455 ?
Cl1 Cl1 C4 53.2(8) 14_455 14_455 ?
Cl1 Cl1 C4 39.4(8) 15 14_455 ?
C4 Cl1 C4 70.8(11) . 14_455 ?
Cl2 Cl1 C4 57.0(9) 15 14_455 ?
C4 Cl1 C4 12.7(16) 13_565 14_455 ?
Cl2 Cl1 Cl2 116(3) 2_665 3_565 ?
Cl2 Cl1 Cl2 39.0(10) 13_565 3_565 ?
C4 Cl1 Cl2 52.1(10) 3_565 3_565 ?
C4 Cl1 Cl2 58.4(9) 2_665 3_565 ?
Cl1 Cl1 Cl2 95.0(6) 14_455 3_565 ?
Cl1 Cl1 Cl2 30.9(4) 15 3_565 ?
C4 Cl1 Cl2 44.7(12) . 3_565 ?
Cl2 Cl1 Cl2 89.1(8) 15 3_565 ?
C4 Cl1 Cl2 59.9(11) 13_565 3_565 ?
C4 Cl1 Cl2 48.7(8) 14_455 3_565 ?
Cl2 Cl1 Cl1 59.3(19) 2_665 3_565 ?
Cl2 Cl1 Cl1 100.9(9) 13_565 3_565 ?
C4 Cl1 Cl1 42.4(10) 3_565 3_565 ?
C4 Cl1 Cl1 30.2(10) 2_665 3_565 ?
Cl1 Cl1 Cl1 43.8(4) 14_455 3_565 ?
Cl1 Cl1 Cl1 89.998(1) 15 3_565 ?
C4 Cl1 Cl1 42.0(10) . 3_565 ?
Cl2 Cl1 Cl1 27.5(6) 15 3_565 ?
C4 Cl1 Cl1 54.4(9) 13_565 3_565 ?
C4 Cl1 Cl1 60.2(8) 14_455 3_565 ?
Cl2 Cl1 Cl1 71.5(4) 3_565 3_565 ?
Cl1 Cl2 Cl1 148(3) 3_565 13_565 ?
Cl1 Cl2 Cl2 44.9(15) 3_565 15 ?
Cl1 Cl2 Cl2 112.1(15) 13_565 15 ?
Cl1 Cl2 Cl2 135.0(19) 3_565 14_455 ?
Cl1 Cl2 Cl2 22.1(10) 13_565 14_455 ?
Cl2 Cl2 Cl2 115.1(9) 15 14_455 ?
Cl1 Cl2 C4 56(2) 3_565 2_665 ?
Cl1 Cl2 C4 99.1(13) 13_565 2_665 ?
Cl2 Cl2 C4 70.7(12) 15 2_665 ?
Cl2 Cl2 C4 79.9(10) 14_455 2_665 ?
Cl1 Cl2 C4 71(2) 3_565 . ?
Cl1 Cl2 C4 85.7(14) 13_565 . ?
Cl2 Cl2 C4 81.0(10) 15 . ?
Cl2 Cl2 C4 65.7(12) 14_455 . ?
C4 Cl2 C4 14.6(16) 2_665 . ?
Cl1 Cl2 C4 105(2) 3_565 15 ?
Cl1 Cl2 C4 48.3(13) 13_565 15 ?
Cl2 Cl2 C4 63.7(12) 15 15 ?
Cl2 Cl2 C4 56.3(15) 14_455 15 ?
C4 Cl2 C4 83.4(16) 2_665 15 ?
C4 Cl2 C4 78.5(14) . 15 ?
Cl1 Cl2 C4 60.7(15) 3_565 3_565 ?
Cl1 Cl2 C4 92.5(15) 13_565 3_565 ?
Cl2 Cl2 C4 68.3(11) 15 3_565 ?
Cl2 Cl2 C4 74.6(11) 14_455 3_565 ?
C4 Cl2 C4 8.3(9) 2_665 3_565 ?
C4 Cl2 C4 12.8(17) . 3_565 ?
C4 Cl2 C4 75.2(11) 15 3_565 ?
Cl1 Cl2 C4 92(2) 3_565 13_565 ?
Cl1 Cl2 C4 60.7(13) 13_565 13_565 ?
Cl2 Cl2 C4 51.4(12) 15 13_565 ?
Cl2 Cl2 C4 66.5(11) 14_455 13_565 ?
C4 Cl2 C4 77.2(16) 2_665 13_565 ?
C4 Cl2 C4 75.2(11) . 13_565 ?
C4 Cl2 C4 12.7(18) 15 13_565 ?
C4 Cl2 C4 69.3(13) 3_565 13_565 ?
Cl1 Cl2 Cl1 54.7(19) 3_565 14_455 ?
Cl1 Cl2 Cl1 99.9(13) 13_565 14_455 ?
Cl2 Cl2 Cl1 12.6(6) 15 14_455 ?
Cl2 Cl2 Cl1 102.6(8) 14_455 14_455 ?
C4 Cl2 Cl1 68.1(11) 2_665 14_455 ?
C4 Cl2 Cl1 76.0(9) . 14_455 ?
C4 Cl2 Cl1 51.7(12) 15 14_455 ?
C4 Cl2 Cl1 64.1(11) 3_565 14_455 ?
C4 Cl2 Cl1 39.2(10) 13_565 14_455 ?
Cl1 Cl2 C4 100(2) 3_565 14_455 ?
Cl1 Cl2 C4 50.7(12) 13_565 14_455 ?
Cl2 Cl2 C4 62.3(10) 15 14_455 ?
Cl2 Cl2 C4 54.5(8) 14_455 14_455 ?
C4 Cl2 C4 74.6(12) 2_665 14_455 ?
C4 Cl2 C4 69.7(16) . 14_455 ?
C4 Cl2 C4 8.9(10) 15 14_455 ?
C4 Cl2 C4 66.3(15) 3_565 14_455 ?
C4 Cl2 C4 12.2(12) 13_565 14_455 ?
Cl1 Cl2 C4 49.7(7) 14_455 14_455 ?
Cl1 Cl2 Cl1 107(2) 3_565 2_665 ?
Cl1 Cl2 Cl1 49.5(8) 13_565 2_665 ?
Cl2 Cl2 Cl1 101.3(5) 15 2_665 ?
Cl2 Cl2 Cl1 28.9(6) 14_455 2_665 ?
C4 Cl2 Cl1 51.1(8) 2_665 2_665 ?
C4 Cl2 Cl1 36.8(11) . 2_665 ?
C4 Cl2 Cl1 61.9(9) 15 2_665 ?
C4 Cl2 Cl1 46.2(11) 3_565 2_665 ?
C4 Cl2 Cl1 66.6(11) 13_565 2_665 ?
Cl1 Cl2 Cl1 90.9(8) 14_455 2_665 ?
C4 Cl2 Cl1 55.5(9) 14_455 2_665 ?
N1 C1 O1 129.4(3) . 16_664 ?
N1 C1 C3 116.9(3) . . ?
O1 C1 C3 113.7(3) 16_664 . ?
N2 C2 N4 126.8(3) . . ?
N2 C2 C3 109.8(3) . . ?
N4 C2 C3 123.4(3) . . ?
N3 C3 C2 108.8(3) . . ?
N3 C3 C1 121.6(3) . . ?
C2 C3 C1 129.6(3) . . ?
C1 N1 O1 115.5(3) . . ?
C2 N2 O2 103.9(3) . . ?
C3 N3 O2 105.8(3) . . ?
C2 N4 N5 123.9(3) . . ?
C2 N4 H4 124(2) . . ?
N5 N4 H4 112(2) . . ?
O4 N5 O3 127.8(3) . . ?
O4 N5 N4 115.3(3) . . ?
O3 N5 N4 116.9(3) . . ?
C1 O1 N1 115.1(2) 16_664 . ?
N3 O2 N2 111.8(2) . . ?

_diffrn_measured_fraction_theta_max 0.982
_diffrn_reflns_theta_full        25.32
_diffrn_measured_fraction_theta_full 0.982
_refine_diff_density_max         0.503
_refine_diff_density_min         -0.369
_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_CCDC6
_database_code_depnum_ccdc_archive 'CCDC 1042140'
_audit_update_record             
;
2015-01-05 deposited with the CCDC.
2017-09-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H6 N14 O16'
_chemical_formula_sum            'C10 H6 N14 O16'
_chemical_formula_weight         578.29

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

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/n
_symmetry_space_group_name_Hall  '-P 2yn'

loop_
_symmetry_equiv_pos_as_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                   6.0094(9)
_cell_length_b                   29.742(5)
_cell_length_c                   6.0976(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 114.883(6)
_cell_angle_gamma                90.00
_cell_volume                     988.7(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    777
_cell_measurement_theta_min      3.80
_cell_measurement_theta_max      21.84

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.943
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             584
_exptl_absorpt_coefficient_mu    0.185
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6334
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_process_details   'SADABS (Bruker, 2013)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71076
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  'TRIUMPH curved crystal monochromator'
_diffrn_measurement_device_type  'PHOTON100 CMOS detector'
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4791
_diffrn_reflns_av_R_equivalents  0.0867
_diffrn_reflns_av_sigmaI/netI    0.1033
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_k_max       35
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_theta_min         3.75
_diffrn_reflns_theta_max         25.36
_reflns_number_total             1781
_reflns_number_gt                999
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0338P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1781
_refine_ls_number_parameters     185
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1284
_refine_ls_R_factor_gt           0.0514
_refine_ls_wR_factor_ref         0.1008
_refine_ls_wR_factor_gt          0.0822
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_restrained_S_all      1.020
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.0495(6) 0.03841(11) 0.2514(6) 0.0186(8) Uani 1 1 d . . .
C2 C -0.0116(6) 0.08369(11) 0.1746(6) 0.0212(8) Uani 1 1 d . . .
C3 C 0.2914(6) 0.01884(12) 0.3860(6) 0.0207(8) Uani 1 1 d . . .
C5 C 0.0594(6) 0.16251(11) 0.1192(6) 0.0208(8) Uani 1 1 d . . .
H5A H 0.1542 0.1852 0.2418 0.025 Uiso 1 1 calc R . .
H5B H -0.1149 0.1653 0.0905 0.025 Uiso 1 1 calc R . .
C6 C 0.0830(6) 0.17217(11) -0.1141(6) 0.0193(8) Uani 1 1 d . . .
N1 N -0.1510(5) 0.01444(10) 0.1797(5) 0.0288(8) Uani 1 1 d . . .
N2 N -0.2483(5) 0.08721(10) 0.0553(5) 0.0275(7) Uani 1 1 d . . .
N3 N 0.4702(5) 0.04626(9) 0.4648(5) 0.0245(7) Uani 1 1 d . . .
N4 N 0.1460(5) 0.11854(10) 0.2108(5) 0.0227(7) Uani 1 1 d . . .
H4 H 0.296(6) 0.1138(12) 0.291(6) 0.027 Uiso 1 1 d . . .
N5 N 0.3499(5) 0.17813(9) -0.0778(6) 0.0258(7) Uani 1 1 d . . .
N6 N -0.0478(5) 0.21577(10) -0.2349(6) 0.0267(7) Uani 1 1 d . . .
N7 N -0.0260(6) 0.13464(11) -0.2959(5) 0.0295(8) Uani 1 1 d . . .
O1 O -0.3376(4) 0.04372(8) 0.0581(4) 0.0310(6) Uani 1 1 d . . .
O2 O 0.2925(4) -0.02640(7) 0.4059(4) 0.0298(7) Uani 1 1 d . . .
O3 O 0.5033(4) 0.17627(8) 0.1294(5) 0.0333(7) Uani 1 1 d . . .
O4 O 0.3872(5) 0.18412(10) -0.2556(5) 0.0488(8) Uani 1 1 d . . .
O5 O -0.1077(4) 0.23976(8) -0.1069(5) 0.0363(7) Uani 1 1 d . . .
O6 O -0.0779(5) 0.22285(9) -0.4411(5) 0.0432(8) Uani 1 1 d . . .
O7 O -0.2456(5) 0.13644(9) -0.4128(5) 0.0464(8) Uani 1 1 d . . .
O8 O 0.1139(5) 0.10497(9) -0.2931(5) 0.0462(8) 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 1.307(4) . ?
C1 C2 1.423(4) . ?
C1 C3 1.456(5) . ?
C2 N2 1.301(4) . ?
C2 N4 1.358(4) . ?
C3 N3 1.271(4) . ?
C3 O2 1.351(4) . ?
C5 N4 1.431(4) . ?
C5 C6 1.515(4) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 N7 1.514(4) . ?
C6 N5 1.534(4) . ?
C6 N6 1.535(4) . ?
N1 O1 1.366(3) . ?
N2 O1 1.403(3) . ?
N3 O2 1.435(3) 3_656 ?
N4 H4 0.84(3) . ?
N5 O4 1.209(3) . ?
N5 O3 1.212(3) . ?
N6 O6 1.211(4) . ?
N6 O5 1.219(3) . ?
N7 O7 1.209(3) . ?
N7 O8 1.214(4) . ?
O2 N3 1.435(3) 3_656 ?

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 C2 109.4(3) . . ?
N1 C1 C3 122.1(3) . . ?
C2 C1 C3 128.5(3) . . ?
N2 C2 N4 123.6(3) . . ?
N2 C2 C1 109.3(3) . . ?
N4 C2 C1 127.1(3) . . ?
N3 C3 O2 129.3(3) . . ?
N3 C3 C1 116.2(3) . . ?
O2 C3 C1 114.5(3) . . ?
N4 C5 C6 112.2(3) . . ?
N4 C5 H5A 109.2 . . ?
C6 C5 H5A 109.2 . . ?
N4 C5 H5B 109.2 . . ?
C6 C5 H5B 109.2 . . ?
H5A C5 H5B 107.9 . . ?
N7 C6 C5 111.4(3) . . ?
N7 C6 N5 107.1(3) . . ?
C5 C6 N5 113.1(3) . . ?
N7 C6 N6 107.2(3) . . ?
C5 C6 N6 112.3(3) . . ?
N5 C6 N6 105.4(2) . . ?
C1 N1 O1 105.4(3) . . ?
C2 N2 O1 104.6(3) . . ?
C3 N3 O2 115.5(3) . 3_656 ?
C2 N4 C5 121.3(3) . . ?
C2 N4 H4 118(2) . . ?
C5 N4 H4 120(2) . . ?
O4 N5 O3 126.5(3) . . ?
O4 N5 C6 117.7(3) . . ?
O3 N5 C6 115.8(3) . . ?
O6 N6 O5 127.5(3) . . ?
O6 N6 C6 117.9(3) . . ?
O5 N6 C6 114.6(3) . . ?
O7 N7 O8 128.2(3) . . ?
O7 N7 C6 115.3(3) . . ?
O8 N7 C6 116.2(3) . . ?
N1 O1 N2 111.3(2) . . ?
C3 O2 N3 115.2(2) . 3_656 ?

_diffrn_measured_fraction_theta_max 0.981
_diffrn_reflns_theta_full        25.36
_diffrn_measured_fraction_theta_full 0.981
_refine_diff_density_max         0.335
_refine_diff_density_min         -0.239
_refine_diff_density_rms         0.065
