# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 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 1565962'
_audit_update_record             
;
2017-10-15 deposited with the CCDC.
2018-01-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C4 H4 N7 Na O8'
_chemical_formula_weight         301.13

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'
Na Na 0.0362 0.0249 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      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                   7.8182(4)
_cell_length_b                   12.4042(7)
_cell_length_c                   12.0228(7)
_cell_angle_alpha                90
_cell_angle_beta                 103.486(2)
_cell_angle_gamma                90
_cell_volume                     1133.80(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    5818
_cell_measurement_theta_min      2.39
_cell_measurement_theta_max      30.02

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.764
_exptl_crystal_F_000             608
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.198
_shelx_estimated_absorpt_T_min   0.943
_shelx_estimated_absorpt_T_max   0.980
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  CCD
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15228
_diffrn_reflns_av_unetI/netI     0.0167
_diffrn_reflns_av_R_equivalents  0.0208
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.394
_diffrn_reflns_theta_max         31.612
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.915
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.915
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.915
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             3497
_reflns_number_gt                2655
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0537P)²+0.2118P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3497
_refine_ls_number_parameters     181
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0519
_refine_ls_R_factor_gt           0.0363
_refine_ls_wR_factor_ref         0.1052
_refine_ls_wR_factor_gt          0.0948
_refine_ls_goodness_of_fit_ref   0.998
_refine_ls_restrained_S_all      0.998
_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 -0.00313(15) 1.00070(9) 0.17320(10) 0.0355(2) Uani 1 1 d . . . . .
C2 C 0.20226(15) 0.91672(9) 0.09785(10) 0.0362(2) Uani 1 1 d . . . . .
C3 C -0.22070(14) 0.97389(9) 0.23731(10) 0.0350(2) Uani 1 1 d . . . . .
C4 C 0.28726(15) 0.76780(10) 0.05795(10) 0.0359(2) Uani 1 1 d . . . . .
N1 N 0.13584(14) 1.00709(8) 0.12848(10) 0.0420(2) Uani 1 1 d . . . . .
N2 N 0.16851(12) 0.81310(8) 0.10786(9) 0.0348(2) Uani 1 1 d . . . . .
N3 N -0.10161(13) 0.91998(7) 0.19443(8) 0.0348(2) Uani 1 1 d . . . . .
N4 N 0.39198(16) 0.82916(10) 0.01775(10) 0.0473(3) Uani 1 1 d . . . . .
N5 N -0.21054(14) 1.07788(8) 0.24628(10) 0.0427(2) Uani 1 1 d . . . . .
N6 N 0.30262(14) 0.65072(9) 0.05033(10) 0.0430(2) Uani 1 1 d . . . . .
N7 N -0.36198(14) 0.91837(9) 0.27391(10) 0.0435(2) Uani 1 1 d . . . . .
O1 O -0.06172(12) 1.09815(7) 0.20281(9) 0.0461(2) Uani 1 1 d . . . . .
O2 O 0.33644(13) 0.93212(8) 0.04381(9) 0.0496(2) Uani 1 1 d . . . . .
O3 O -0.46598(14) 0.97363(9) 0.31035(11) 0.0614(3) Uani 1 1 d . . . . .
O4 O 0.39964(17) 0.61581(11) -0.00654(12) 0.0724(3) Uani 1 1 d . . . . .
O5 O -0.36706(16) 0.82088(9) 0.26434(13) 0.0684(3) Uani 1 1 d . . . . .
O6 O 0.21725(15) 0.59660(8) 0.10186(11) 0.0601(3) Uani 1 1 d . . . . .
O7 O -0.17453(18) 0.65142(10) -0.00872(10) 0.0715(4) Uani 1 1 d D . . . .
H3 H -0.2238 0.6926 -0.0637 0.086 Uiso 1 1 d R U . . .
H4 H -0.1827 0.5894 -0.0392 0.086 Uiso 1 1 d R U . . .
O8 O 0.12011(12) 0.68827(7) 0.35429(8) 0.0429(2) Uani 1 1 d D . . . .
H1 H 0.1944 0.6370 0.3626 0.052 Uiso 1 1 d R U . . .
H2 H 0.0723 0.6737 0.4092 0.052 Uiso 1 1 d R U . . .
Na1 Na -0.06911(7) 0.71271(4) 0.17459(4) 0.04458(14) 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 1.3222(16) . ?
C1 N3 1.3236(15) . ?
C1 O1 1.3689(14) . ?
C2 N1 1.3232(15) . ?
C2 N2 1.3233(14) . ?
C2 O2 1.3701(14) . ?
C3 N5 1.2953(15) . ?
C3 N3 1.3430(14) . ?
C3 N7 1.4542(15) . ?
C4 N4 1.2914(16) . ?
C4 N2 1.3408(14) . ?
C4 N6 1.4618(16) . ?
N2 Na1 2.5180(10) . ?
N3 Na1 2.5999(10) . ?
N4 O2 1.4076(15) . ?
N5 O1 1.4049(14) . ?
N5 Na1 2.7267(11) 2_455 ?
N6 O4 1.2134(15) . ?
N6 O6 1.2137(15) . ?
N7 O5 1.2146(15) . ?
N7 O3 1.2202(14) . ?
O3 Na1 2.9799(13) 2_455 ?
O7 Na1 2.2950(13) . ?
O7 H3 0.8525 . ?
O7 H4 0.8485 . ?
O8 Na1 2.3362(11) . ?
O8 H1 0.8512 . ?
O8 H2 0.8508 . ?
Na1 N5 2.7267(11) 2_445 ?
Na1 O3 2.9799(13) 2_445 ?

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 N3 133.94(11) . . ?
N1 C1 O1 114.16(10) . . ?
N3 C1 O1 111.89(10) . . ?
N1 C2 N2 134.27(11) . . ?
N1 C2 O2 114.05(10) . . ?
N2 C2 O2 111.68(10) . . ?
N5 C3 N3 119.55(11) . . ?
N5 C3 N7 118.85(10) . . ?
N3 C3 N7 121.60(10) . . ?
N4 C4 N2 119.09(11) . . ?
N4 C4 N6 119.57(10) . . ?
N2 C4 N6 121.33(10) . . ?
C1 N1 C2 118.38(10) . . ?
C2 N2 C4 101.12(9) . . ?
C2 N2 Na1 133.38(8) . . ?
C4 N2 Na1 125.08(8) . . ?
C1 N3 C3 100.60(9) . . ?
C1 N3 Na1 131.04(8) . . ?
C3 N3 Na1 128.23(8) . . ?
C4 N4 O2 101.30(9) . . ?
C3 N5 O1 100.80(9) . . ?
C3 N5 Na1 127.47(8) . 2_455 ?
O1 N5 Na1 131.72(7) . 2_455 ?
O4 N6 O6 125.50(12) . . ?
O4 N6 C4 117.46(12) . . ?
O6 N6 C4 117.03(10) . . ?
O5 N7 O3 125.71(11) . . ?
O5 N7 C3 116.95(11) . . ?
O3 N7 C3 117.34(11) . . ?
C1 O1 N5 107.16(8) . . ?
C2 O2 N4 106.81(9) . . ?
N7 O3 Na1 121.42(8) . 2_455 ?
Na1 O7 H3 122.8 . . ?
Na1 O7 H4 133.6 . . ?
H3 O7 H4 103.5 . . ?
Na1 O8 H1 118.2 . . ?
Na1 O8 H2 116.6 . . ?
H1 O8 H2 99.3 . . ?
O7 Na1 O8 148.57(4) . . ?
O7 Na1 N2 89.10(5) . . ?
O8 Na1 N2 90.21(4) . . ?
O7 Na1 N3 113.25(4) . . ?
O8 Na1 N3 95.61(3) . . ?
N2 Na1 N3 68.62(3) . . ?
O7 Na1 N5 90.99(5) . 2_445 ?
O8 Na1 N5 85.01(4) . 2_445 ?
N2 Na1 N5 170.97(4) . 2_445 ?
N3 Na1 N5 119.43(4) . 2_445 ?
O7 Na1 O3 74.69(4) . 2_445 ?
O8 Na1 O3 77.59(4) . 2_445 ?
N2 Na1 O3 116.56(3) . 2_445 ?
N3 Na1 O3 171.16(4) . 2_445 ?
N5 Na1 O3 54.90(3) 2_445 2_445 ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N3 C1 N1 C2 -1.7(2) . . . . ?
O1 C1 N1 C2 179.64(11) . . . . ?
N2 C2 N1 C1 -5.4(2) . . . . ?
O2 C2 N1 C1 174.84(11) . . . . ?
N1 C2 N2 C4 -179.79(14) . . . . ?
O2 C2 N2 C4 0.02(13) . . . . ?
N1 C2 N2 Na1 7.6(2) . . . . ?
O2 C2 N2 Na1 -172.55(8) . . . . ?
N4 C4 N2 C2 0.08(15) . . . . ?
N6 C4 N2 C2 178.83(11) . . . . ?
N4 C4 N2 Na1 173.48(9) . . . . ?
N6 C4 N2 Na1 -7.77(15) . . . . ?
N1 C1 N3 C3 -178.52(14) . . . . ?
O1 C1 N3 C3 0.20(13) . . . . ?
N1 C1 N3 Na1 5.4(2) . . . . ?
O1 C1 N3 Na1 -175.92(7) . . . . ?
N5 C3 N3 C1 -0.15(14) . . . . ?
N7 C3 N3 C1 179.68(11) . . . . ?
N5 C3 N3 Na1 176.12(9) . . . . ?
N7 C3 N3 Na1 -4.05(16) . . . . ?
N2 C4 N4 O2 -0.14(15) . . . . ?
N6 C4 N4 O2 -178.91(10) . . . . ?
N3 C3 N5 O1 0.03(15) . . . . ?
N7 C3 N5 O1 -179.80(10) . . . . ?
N3 C3 N5 Na1 178.90(8) . . . 2_455 ?
N7 C3 N5 Na1 -0.94(17) . . . 2_455 ?
N4 C4 N6 O4 -8.95(18) . . . . ?
N2 C4 N6 O4 172.31(12) . . . . ?
N4 C4 N6 O6 170.87(12) . . . . ?
N2 C4 N6 O6 -7.88(17) . . . . ?
N5 C3 N7 O5 -179.90(13) . . . . ?
N3 C3 N7 O5 0.27(18) . . . . ?
N5 C3 N7 O3 0.85(18) . . . . ?
N3 C3 N7 O3 -178.98(11) . . . . ?
N1 C1 O1 N5 178.79(10) . . . . ?
N3 C1 O1 N5 -0.20(14) . . . . ?
C3 N5 O1 C1 0.09(13) . . . . ?
Na1 N5 O1 C1 -178.70(8) 2_455 . . . ?
N1 C2 O2 N4 179.76(11) . . . . ?
N2 C2 O2 N4 -0.09(14) . . . . ?
C4 N4 O2 C2 0.13(13) . . . . ?
O5 N7 O3 Na1 -179.59(12) . . . 2_455 ?
C3 N7 O3 Na1 -0.42(16) . . . 2_455 ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O7 H4 O6 0.85 2.42 3.2644(16) 171.9 3_565
O7 H3 O8 0.85 2.02 2.8304(15) 158.2 4_575
O8 H2 N4 0.85 2.13 2.9537(14) 162.0 4_576
O8 H1 N1 0.85 2.07 2.9240(13) 175.7 2_545
O7 H4 O6 0.85 2.42 3.2644(16) 171.9 3_565
O7 H3 O8 0.85 2.02 2.8304(15) 158.2 4_575
O8 H2 N4 0.85 2.13 2.9537(14) 162.0 4_576
O8 H1 N1 0.85 2.07 2.9240(13) 175.7 2_545
O7 H4 O6 0.85 2.42 3.2644(16) 171.9 3_565
O7 H3 O8 0.85 2.02 2.8304(15) 158.2 4_575
O8 H2 N4 0.85 2.13 2.9537(14) 162.0 4_576
O8 H1 N1 0.85 2.07 2.9240(13) 175.7 2_545
O7 H4 O6 0.85 2.42 3.2644(16) 171.9 3_565
O7 H3 O8 0.85 2.02 2.8304(15) 158.2 4_575
O8 H2 N4 0.85 2.13 2.9537(14) 162.0 4_576
O8 H1 N1 0.85 2.07 2.9240(13) 175.7 2_545
O7 H4 O6 0.85 2.42 3.2644(16) 171.9 3_565
O7 H3 O8 0.85 2.02 2.8304(15) 158.2 4_575
O8 H2 N4 0.85 2.13 2.9537(14) 162.0 4_576
O8 H1 N1 0.85 2.07 2.9240(13) 175.7 2_545
O7 H4 O6 0.85 2.42 3.2644(16) 171.9 3_565
O7 H3 O8 0.85 2.02 2.8304(15) 158.2 4_575
O8 H2 N4 0.85 2.13 2.9537(14) 162.0 4_576
O8 H1 N1 0.85 2.07 2.9240(13) 175.7 2_545
O7 H4 O6 0.85 2.42 3.2644(16) 171.9 3_565
O7 H3 O8 0.85 2.02 2.8304(15) 158.2 4_575
O8 H2 N4 0.85 2.13 2.9537(14) 162.0 4_576
O8 H1 N1 0.85 2.07 2.9240(13) 175.7 2_545
O7 H4 O6 0.85 2.42 3.2644(16) 171.9 3_565
O7 H3 O8 0.85 2.02 2.8304(15) 158.2 4_575
O8 H2 N4 0.85 2.13 2.9537(14) 162.0 4_576
O8 H1 N1 0.85 2.07 2.9240(13) 175.7 2_545
O7 H4 O6 0.85 2.42 3.2644(16) 171.9 3_565
O7 H3 O8 0.85 2.02 2.8304(15) 158.2 4_575
O8 H2 N4 0.85 2.13 2.9537(14) 162.0 4_576
O8 H1 N1 0.85 2.07 2.9240(13) 175.7 2_545
O7 H4 O6 0.85 2.42 3.2644(16) 171.9 3_565
O7 H3 O8 0.85 2.02 2.8304(15) 158.2 4_575
O8 H2 N4 0.85 2.13 2.9537(14) 162.0 4_576
O8 H1 N1 0.85 2.07 2.9240(13) 175.7 2_545
O7 H4 O6 0.85 2.42 3.2644(16) 171.9 3_565
O7 H3 O8 0.85 2.02 2.8304(15) 158.2 4_575
O8 H2 N4 0.85 2.13 2.9537(14) 162.0 4_576
O8 H1 N1 0.85 2.07 2.9240(13) 175.7 2_545
O7 H4 O6 0.85 2.42 3.2644(16) 171.9 3_565
O7 H3 O8 0.85 2.02 2.8304(15) 158.2 4_575
O8 H2 N4 0.85 2.13 2.9537(14) 162.0 4_576
O8 H1 N1 0.85 2.07 2.9240(13) 175.7 2_545
O8 H1 N1 0.85 2.07 2.9240(13) 175.7 2_545
O8 H2 N4 0.85 2.13 2.9537(14) 162.0 4_576
O7 H4 O6 0.85 2.42 3.2644(16) 171.9 3_565
O7 H3 O8 0.85 2.02 2.8304(15) 158.2 4_575
O8 H1 N1 0.85 2.07 2.9240(13) 175.7 2_545
O8 H2 N4 0.85 2.13 2.9537(14) 162.0 4_576
O7 H3 O8 0.85 2.02 2.8304(15) 158.2 4_575
O7 H4 O6 0.85 2.42 3.2644(16) 171.9 3_565
O8 H1 N1 0.85 2.07 2.9240(13) 175.7 2_545
O8 H2 N4 0.85 2.13 2.9537(14) 162.0 4_576
O7 H3 O8 0.85 2.02 2.8304(15) 158.2 4_575
O7 H4 O6 0.85 2.42 3.2644(16) 171.9 3_565
O8 H1 N1 0.85 2.07 2.9240(13) 175.7 2_545
O8 H2 N4 0.85 2.13 2.9537(14) 162.0 4_576
O7 H3 O8 0.85 2.02 2.8304(15) 158.2 4_575
O7 H4 O6 0.85 2.42 3.2644(16) 171.9 3_565
O8 H1 N1 0.85 2.07 2.9240(13) 175.7 2_545
O8 H2 N4 0.85 2.13 2.9537(14) 162.0 4_576
O7 H3 O8 0.85 2.02 2.8304(15) 158.2 4_575
O7 H4 O6 0.85 2.42 3.2644(16) 171.9 3_565
O8 H1 N1 0.85 2.07 2.9240(13) 175.7 2_545
O8 H2 N4 0.85 2.13 2.9537(14) 162.0 4_576
O7 H3 O8 0.85 2.02 2.8304(15) 158.2 4_575
O8 H1 N1 0.85 2.07 2.9240(13) 175.7 2_545
O8 H2 N4 0.85 2.13 2.9537(14) 162.0 4_576
O7 H3 O8 0.85 2.02 2.8304(15) 158.2 4_575
O7 H4 O6 0.85 2.42 3.2644(16) 171.9 3_565
O8 H1 N1 0.85 2.07 2.9240(13) 175.7 2_545
O8 H2 N4 0.85 2.13 2.9537(14) 162.0 4_576
O7 H3 O8 0.85 2.02 2.8304(15) 158.2 4_575
O7 H4 O6 0.85 2.42 3.2644(16) 171.9 3_565
O8 H1 N1 0.85 2.07 2.9240(13) 175.7 2_545
O8 H2 N4 0.85 2.13 2.9537(14) 162.0 4_576
O7 H3 O8 0.85 2.02 2.8304(15) 158.2 4_575
O8 H1 N1 0.85 2.07 2.9240(13) 175.7 2_545
O8 H2 N4 0.85 2.13 2.9537(14) 162.0 4_576
O7 H3 O8 0.85 2.02 2.8304(15) 158.2 4_575
O7 H4 O6 0.85 2.42 3.2644(16) 171.9 3_565
O8 H1 N1 0.85 2.07 2.9240(13) 175.7 2_545
O8 H2 N4 0.85 2.13 2.9537(14) 162.0 4_576
O7 H3 O8 0.85 2.02 2.8304(15) 158.2 4_575
O7 H4 O6 0.85 2.42 3.2644(16) 171.9 3_565
O8 H1 N1 0.85 2.07 2.9240(13) 175.7 2_545
O8 H2 N4 0.85 2.13 2.9537(14) 162.0 4_576
O7 H3 O8 0.85 2.02 2.8304(15) 158.2 4_575
O7 H4 O6 0.85 2.42 3.2644(16) 171.9 3_565
O8 H1 N1 0.85 2.07 2.9240(13) 175.7 2_545
O8 H2 N4 0.85 2.13 2.9537(14) 162.0 4_576
O7 H3 O8 0.85 2.02 2.8304(15) 158.2 4_575
O7 H4 O6 0.85 2.42 3.2644(16) 171.9 3_565
O8 H1 N1 0.85 2.07 2.9240(13) 175.7 2_545
O8 H2 N4 0.85 2.13 2.9537(14) 162.0 4_576
O7 H3 O8 0.85 2.02 2.8304(15) 158.2 4_575
O7 H4 O6 0.85 2.42 3.2644(16) 171.9 3_565

_refine_diff_density_max         0.227
_refine_diff_density_min         -0.220
_refine_diff_density_rms         0.042

_shelxl_version_number           2014-3

####################################################################### 
# 
# 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_2
_database_code_depnum_ccdc_archive 'CCDC 1565963'
_audit_update_record             
;
2017-10-15 deposited with the CCDC.
2018-01-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C5 H8 N12 O6'
_chemical_formula_weight         332.23

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

_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'

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

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

_cell_length_a                   12.6832(10)
_cell_length_b                   14.8873(12)
_cell_length_c                   6.9071(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1304.19(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    7180
_cell_measurement_theta_min      2.74
_cell_measurement_theta_max      30.52

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.692
_exptl_crystal_F_000             680
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.151
_shelx_estimated_absorpt_T_min   0.956
_shelx_estimated_absorpt_T_max   0.985
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  CCD
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12555
_diffrn_reflns_av_unetI/netI     0.0121
_diffrn_reflns_av_R_equivalents  0.0175
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         2.109
_diffrn_reflns_theta_max         25.480
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2429
_reflns_number_gt                2306
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.836
_reflns_Friedel_fraction_max     0.998
_reflns_Friedel_fraction_full    0.998

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0433P)²+0.2499P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1018 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.5(3)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2429
_refine_ls_number_parameters     208
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0309
_refine_ls_R_factor_gt           0.0292
_refine_ls_wR_factor_ref         0.0775
_refine_ls_wR_factor_gt          0.0764
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_restrained_S_all      1.044
_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 0.48819(17) 0.41662(15) 0.2630(4) 0.0352(5) Uani 1 1 d . . . . .
C2 C 0.44204(17) 0.56469(14) 0.2673(4) 0.0353(5) Uani 1 1 d . . . . .
C3 C 0.43139(18) 0.28931(15) 0.3032(4) 0.0384(5) Uani 1 1 d . . . . .
C4 C 0.31691(19) 0.64959(16) 0.3097(4) 0.0415(5) Uani 1 1 d . . . . .
C5 C 0.19566(16) 0.44170(13) 0.7812(3) 0.0323(5) Uani 1 1 d . . . . .
N1 N 0.51573(14) 0.50225(14) 0.2432(3) 0.0407(5) Uani 1 1 d . . . . .
N2 N 0.52721(18) 0.27071(14) 0.2550(4) 0.0537(6) Uani 1 1 d . . . . .
N3 N 0.39102(18) 0.70790(14) 0.2877(4) 0.0564(6) Uani 1 1 d . . . . .
N4 N 0.40061(14) 0.37526(12) 0.3136(3) 0.0374(4) Uani 1 1 d . . . . .
N5 N 0.33970(14) 0.56163(12) 0.2986(3) 0.0363(4) Uani 1 1 d . . . . .
N6 N 0.36017(19) 0.21521(15) 0.3477(4) 0.0543(6) Uani 1 1 d . . . . .
N7 N 0.20919(18) 0.67996(16) 0.3467(4) 0.0584(7) Uani 1 1 d . . . . .
N8 N 0.26873(16) 0.46392(15) 0.9069(4) 0.0468(5) Uani 1 1 d . . . . .
H8A H 0.3321 0.4743 0.8684 0.056 Uiso 1 1 d R U . . .
H8B H 0.2533 0.4682 1.0277 0.056 Uiso 1 1 d R U . . .
N9 N 0.09668(14) 0.42691(13) 0.8360(3) 0.0360(4) Uani 1 1 d . . . . .
H9 H 0.0479 0.4181 0.7517 0.043 Uiso 1 1 d R U . . .
N10 N 0.07395(19) 0.4259(2) 1.0338(3) 0.0566(6) Uani 1 1 d . . . . .
H10A H 0.0639 0.3697 1.0724 0.068 Uiso 1 1 d R U . . .
H10B H 0.0158 0.4576 1.0553 0.068 Uiso 1 1 d R U . . .
N11 N 0.21925(18) 0.43518(17) 0.5953(3) 0.0502(6) Uani 1 1 d . . . . .
H11 H 0.2828 0.4437 0.5557 0.060 Uiso 1 1 d R U . . .
N12 N 0.1394(2) 0.41402(19) 0.4650(3) 0.0583(7) Uani 1 1 d . . . . .
H12A H 0.1518 0.3601 0.4144 0.070 Uiso 1 1 d R U . . .
H12B H 0.1382 0.4548 0.3711 0.070 Uiso 1 1 d R U . . .
O1 O 0.56772(14) 0.35747(13) 0.2254(3) 0.0551(5) Uani 1 1 d . . . . .
O2 O 0.47801(14) 0.65086(11) 0.2564(4) 0.0559(5) Uani 1 1 d . . . . .
O3 O 0.3899(2) 0.14043(14) 0.3078(6) 0.0960(10) Uani 1 1 d . . . . .
O4 O 0.27649(16) 0.23327(15) 0.4229(5) 0.0743(7) Uani 1 1 d . . . . .
O5 O 0.1977(2) 0.75532(16) 0.4093(6) 0.0969(10) Uani 1 1 d . . . . .
O6 O 0.13864(16) 0.62740(17) 0.3100(6) 0.0868(9) 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 N4 1.317(3) . ?
C1 N1 1.329(3) . ?
C1 O1 1.364(3) . ?
C2 N5 1.317(3) . ?
C2 N1 1.329(3) . ?
C2 O2 1.364(3) . ?
C3 N2 1.290(3) . ?
C3 N4 1.340(3) . ?
C3 N6 1.459(3) . ?
C4 N3 1.288(3) . ?
C4 N5 1.343(3) . ?
C4 N7 1.462(3) . ?
C5 N8 1.312(3) . ?
C5 N11 1.322(3) . ?
C5 N9 1.330(3) . ?
N2 O1 1.405(3) . ?
N3 O2 1.409(3) . ?
N6 O3 1.207(3) . ?
N6 O4 1.212(3) . ?
N7 O5 1.211(4) . ?
N7 O6 1.215(3) . ?
N8 H8A 0.8600 . ?
N8 H8B 0.8600 . ?
N9 N10 1.396(3) . ?
N9 H9 0.8600 . ?
N10 H10A 0.8875 . ?
N10 H10B 0.8878 . ?
N11 N12 1.391(3) . ?
N11 H11 0.8600 . ?
N12 H12A 0.8887 . ?
N12 H12B 0.8887 . ?

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
N4 C1 N1 134.2(2) . . ?
N4 C1 O1 111.9(2) . . ?
N1 C1 O1 113.91(19) . . ?
N5 C2 N1 133.6(2) . . ?
N5 C2 O2 111.8(2) . . ?
N1 C2 O2 114.57(19) . . ?
N2 C3 N4 119.6(2) . . ?
N2 C3 N6 118.4(2) . . ?
N4 C3 N6 122.0(2) . . ?
N3 C4 N5 119.5(2) . . ?
N3 C4 N7 119.6(2) . . ?
N5 C4 N7 120.8(2) . . ?
N8 C5 N11 120.1(2) . . ?
N8 C5 N9 121.3(2) . . ?
N11 C5 N9 118.6(2) . . ?
C2 N1 C1 118.25(19) . . ?
C3 N2 O1 100.65(18) . . ?
C4 N3 O2 100.57(19) . . ?
C1 N4 C3 100.75(18) . . ?
C2 N5 C4 100.82(18) . . ?
O3 N6 O4 125.2(2) . . ?
O3 N6 C3 117.1(2) . . ?
O4 N6 C3 117.7(2) . . ?
O5 N7 O6 125.6(3) . . ?
O5 N7 C4 117.5(2) . . ?
O6 N7 C4 116.9(2) . . ?
C5 N8 H8A 120.0 . . ?
C5 N8 H8B 120.0 . . ?
H8A N8 H8B 120.0 . . ?
C5 N9 N10 118.4(2) . . ?
C5 N9 H9 120.8 . . ?
N10 N9 H9 120.8 . . ?
N9 N10 H10A 109.5 . . ?
N9 N10 H10B 109.3 . . ?
H10A N10 H10B 109.4 . . ?
C5 N11 N12 118.7(2) . . ?
C5 N11 H11 120.6 . . ?
N12 N11 H11 120.7 . . ?
N11 N12 H12A 109.2 . . ?
N11 N12 H12B 109.2 . . ?
H12A N12 H12B 109.4 . . ?
C1 O1 N2 107.18(18) . . ?
C2 O2 N3 107.24(18) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N5 C2 N1 C1 -4.5(4) . . . . ?
O2 C2 N1 C1 176.1(2) . . . . ?
N4 C1 N1 C2 -4.3(4) . . . . ?
O1 C1 N1 C2 176.7(2) . . . . ?
N4 C3 N2 O1 -0.9(3) . . . . ?
N6 C3 N2 O1 -179.9(2) . . . . ?
N5 C4 N3 O2 0.1(4) . . . . ?
N7 C4 N3 O2 -180.0(2) . . . . ?
N1 C1 N4 C3 -179.4(3) . . . . ?
O1 C1 N4 C3 -0.4(3) . . . . ?
N2 C3 N4 C1 0.9(3) . . . . ?
N6 C3 N4 C1 179.9(2) . . . . ?
N1 C2 N5 C4 179.4(3) . . . . ?
O2 C2 N5 C4 -1.2(3) . . . . ?
N3 C4 N5 C2 0.7(3) . . . . ?
N7 C4 N5 C2 -179.2(3) . . . . ?
N2 C3 N6 O3 -11.3(4) . . . . ?
N4 C3 N6 O3 169.7(4) . . . . ?
N2 C3 N6 O4 168.1(3) . . . . ?
N4 C3 N6 O4 -10.9(4) . . . . ?
N3 C4 N7 O5 -20.6(5) . . . . ?
N5 C4 N7 O5 159.3(3) . . . . ?
N3 C4 N7 O6 158.8(3) . . . . ?
N5 C4 N7 O6 -21.3(4) . . . . ?
N8 C5 N9 N10 -6.9(4) . . . . ?
N11 C5 N9 N10 174.3(2) . . . . ?
N8 C5 N11 N12 -178.2(2) . . . . ?
N9 C5 N11 N12 0.6(4) . . . . ?
N4 C1 O1 N2 -0.1(3) . . . . ?
N1 C1 O1 N2 179.2(2) . . . . ?
C3 N2 O1 C1 0.5(3) . . . . ?
N5 C2 O2 N3 1.4(3) . . . . ?
N1 C2 O2 N3 -179.1(2) . . . . ?
C4 N3 O2 C2 -0.8(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N12 H12B O6 0.89 2.60 3.352(4) 142.4 .
N12 H12B N10 0.89 2.51 3.097(3) 124.5 1_554
N12 H12A O4 0.89 2.46 3.217(3) 142.7 .
N11 H11 N5 0.86 2.60 3.174(3) 125.3 .
N11 H11 N4 0.86 2.46 3.142(3) 136.3 .
N10 H10A N2 0.89 2.48 3.354(4) 166.5 4_456
N9 H9 O6 0.86 2.49 3.097(3) 127.9 2_565
N8 H8B N5 0.86 2.58 3.201(3) 130.4 1_556
N8 H8A N1 0.86 2.14 3.001(3) 174.2 2_665
N8 H8A N1 0.86 2.14 3.001(3) 174.2 2_665
N8 H8B N5 0.86 2.58 3.201(3) 130.4 1_556
N9 H9 O6 0.86 2.49 3.097(3) 127.9 2_565
N10 H10A N2 0.89 2.48 3.354(4) 166.5 4_456
N11 H11 N4 0.86 2.46 3.142(3) 136.3 .
N11 H11 N5 0.86 2.60 3.174(3) 125.3 .
N12 H12A O4 0.89 2.46 3.217(3) 142.7 .
N12 H12B N10 0.89 2.51 3.097(3) 124.5 1_554
N12 H12B O6 0.89 2.60 3.352(4) 142.4 .

_refine_diff_density_max         0.151
_refine_diff_density_min         -0.160
_refine_diff_density_rms         0.031

_shelxl_version_number           2014-3

####################################################################### 
# 
# 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_3
_database_code_depnum_ccdc_archive 'CCDC 1565964'
_audit_update_record             
;
2017-10-15 deposited with the CCDC.
2018-01-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C9 H14 N10 O8'
_chemical_formula_weight         390.30

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 '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'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           57
_space_group_name_H-M_alt        'P b c m'
_space_group_name_Hall           '-P 2c 2b'

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

_cell_length_a                   16.141(3)
_cell_length_b                   16.706(3)
_cell_length_c                   6.4305(12)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1734.0(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4499
_cell_measurement_theta_min      2.44
_cell_measurement_theta_max      26.24

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.495
_exptl_crystal_F_000             808
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.131
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  CCD
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            20473
_diffrn_reflns_av_unetI/netI     0.0403
_diffrn_reflns_av_R_equivalents  0.0717
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         1.754
_diffrn_reflns_theta_max         28.588
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measured_fraction_theta_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_point_group_measured_fraction_full 0.990
_reflns_number_total             2390
_reflns_number_gt                1595
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0652P)²+0.3991P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2390
_refine_ls_number_parameters     165
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0845
_refine_ls_R_factor_gt           0.0543
_refine_ls_wR_factor_ref         0.1478
_refine_ls_wR_factor_gt          0.1298
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.038
_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
O4 O 0.52719(10) 0.17486(9) 0.7500 0.0562(5) Uani 1 2 d S T P . .
O1 O 0.67763(11) -0.02250(10) 0.7500 0.0648(5) Uani 1 2 d S T P . .
O3 O 0.82310(13) 0.19660(14) 0.7500 0.1075(10) Uani 1 2 d S T P . .
O6 O 0.25850(16) 0.14590(17) 0.7500 0.1508(16) Uani 1 2 d S T P . .
O2 O 0.89699(13) 0.09088(15) 0.7500 0.0941(8) Uani 1 2 d S T P . .
O5 O 0.29870(18) 0.26874(16) 0.7500 0.181(2) Uani 1 2 d S T P . .
N1 N 0.55052(12) 0.03509(10) 0.7500 0.0462(5) Uani 1 2 d S T P . .
N2 N 0.67984(11) 0.11038(10) 0.7500 0.0419(4) Uani 1 2 d S T P . .
N3 N 0.76168(14) -0.00010(13) 0.7500 0.0689(7) Uani 1 2 d S T P . .
N6 N 0.45556(14) 0.22430(12) 0.7500 0.0743(8) Uani 1 2 d S T P . .
N5 N 0.41841(13) 0.09375(12) 0.7500 0.0603(6) Uani 1 2 d S T P . .
N4 N 0.83084(13) 0.12537(15) 0.7500 0.0650(6) Uani 1 2 d S T P . .
N7 N 0.31072(18) 0.19738(17) 0.7500 0.1198(15) Uani 1 2 d S T P . .
C2 C 0.50062(15) 0.09703(12) 0.7500 0.0453(5) Uani 1 2 d S T P . .
C1 C 0.63239(15) 0.04607(12) 0.7500 0.0429(5) Uani 1 2 d S T P . .
C4 C 0.39749(17) 0.17089(15) 0.7500 0.0690(9) Uani 1 2 d S T P . .
C3 C 0.75559(15) 0.07662(14) 0.7500 0.0482(6) Uani 1 2 d S T P . .
N10 N 0.55023(12) 0.37963(10) 0.7500 0.0491(5) Uani 1 2 d S T P . .
H10A H 0.5260 0.4255 0.7500 0.059 Uiso 1 2 calc R U P . .
H10B H 0.5213 0.3364 0.7500 0.059 Uiso 1 2 calc R U P . .
N8 N 0.67035(13) 0.30542(10) 0.7500 0.0507(5) Uani 1 2 d S T P . .
H8A H 0.6421 0.2618 0.7500 0.061 Uiso 1 2 calc R U P . .
H8B H 0.7236 0.3036 0.7500 0.061 Uiso 1 2 calc R U P . .
O7 O 0.84699(12) 0.39619(12) 0.7500 0.0795(7) Uani 1 2 d S T P . .
N9 N 0.67614(12) 0.44221(10) 0.7500 0.0460(5) Uani 1 2 d S T P . .
H9A H 0.6518 0.4880 0.7500 0.055 Uiso 1 2 calc R U P . .
H9B H 0.7294 0.4397 0.7500 0.055 Uiso 1 2 calc R U P . .
C5 C 0.63174(14) 0.37565(11) 0.7500 0.0378(5) Uani 1 2 d S T P . .
O8 O 0.98375(11) 0.41369(11) 0.7500 0.0713(6) Uani 1 2 d S T P . .
C7 C 0.90663(15) 0.44010(16) 0.7500 0.0589(7) Uani 1 2 d S T P . .
C6 C 0.90161(19) 0.52817(18) 0.7500 0.0906(12) Uani 1 2 d S T P . .
H6A H 0.9492 0.5499 0.6806 0.136 Uiso 0.5 1 calc R U P . .
H6B H 0.9001 0.5473 0.8907 0.136 Uiso 0.5 1 calc R U P . .
H6C H 0.8523 0.5447 0.6786 0.136 Uiso 0.5 1 calc R U P . .
C8 C 0.9961(2) 0.32792(19) 0.7500 0.0958(12) Uani 1 2 d S T P . .
H8C H 0.9706 0.3045 0.6277 0.115 Uiso 0.5 1 calc R U P . .
H8D H 0.9706 0.3045 0.8723 0.115 Uiso 0.5 1 calc R U P . .
C9 C 1.0862(2) 0.3115(2) 0.7500 0.1074(14) Uani 1 2 d S T P . .
H9C H 1.1132 0.3465 0.8472 0.161 Uiso 0.5 1 calc R U P . .
H9D H 1.1081 0.3206 0.6132 0.161 Uiso 0.5 1 calc R U P . .
H9E H 1.0957 0.2569 0.7896 0.161 Uiso 0.5 1 calc R U P . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O4 C2 1.369(2) . ?
O4 N6 1.421(3) . ?
O1 C1 1.358(3) . ?
O1 N3 1.407(3) . ?
O3 N4 1.197(3) . ?
O6 N7 1.204(4) . ?
O2 N4 1.213(3) . ?
O5 N7 1.208(4) . ?
N1 C2 1.311(3) . ?
N1 C1 1.334(3) . ?
N2 C1 1.319(3) . ?
N2 C3 1.347(3) . ?
N3 C3 1.285(3) . ?
N6 C4 1.294(3) . ?
N5 C2 1.328(3) . ?
N5 C4 1.332(3) . ?
N4 C3 1.462(3) . ?
N7 C4 1.469(4) . ?
N10 C5 1.317(3) . ?
N10 H10A 0.8600 . ?
N10 H10B 0.8600 . ?
N8 C5 1.329(3) . ?
N8 H8A 0.8600 . ?
N8 H8B 0.8600 . ?
O7 C7 1.210(3) . ?
N9 C5 1.323(3) . ?
N9 H9A 0.8600 . ?
N9 H9B 0.8600 . ?
O8 C7 1.321(3) . ?
O8 C8 1.447(4) . ?
C7 C6 1.473(4) . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C8 C9 1.479(5) . ?
C8 H8C 0.9700 . ?
C8 H8D 0.9700 . ?
C9 H9C 0.9600 . ?
C9 H9D 0.9600 . ?
C9 H9E 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 O4 N6 107.28(17) . . ?
C1 O1 N3 107.10(18) . . ?
C2 N1 C1 119.99(18) . . ?
C1 N2 C3 100.72(18) . . ?
C3 N3 O1 101.0(2) . . ?
C4 N6 O4 100.88(19) . . ?
C2 N5 C4 102.32(19) . . ?
O3 N4 O2 124.3(3) . . ?
O3 N4 C3 117.8(2) . . ?
O2 N4 C3 117.8(2) . . ?
O6 N7 O5 126.3(3) . . ?
O6 N7 C4 116.9(3) . . ?
O5 N7 C4 116.8(3) . . ?
N1 C2 N5 125.53(19) . . ?
N1 C2 O4 123.9(2) . . ?
N5 C2 O4 110.6(2) . . ?
N2 C1 N1 133.4(2) . . ?
N2 C1 O1 112.0(2) . . ?
N1 C1 O1 114.61(19) . . ?
N6 C4 N5 118.9(2) . . ?
N6 C4 N7 118.9(2) . . ?
N5 C4 N7 122.2(2) . . ?
N3 C3 N2 119.2(2) . . ?
N3 C3 N4 119.5(2) . . ?
N2 C3 N4 121.4(2) . . ?
C5 N10 H10A 120.0 . . ?
C5 N10 H10B 120.0 . . ?
H10A N10 H10B 120.0 . . ?
C5 N8 H8A 120.0 . . ?
C5 N8 H8B 120.0 . . ?
H8A N8 H8B 120.0 . . ?
C5 N9 H9A 120.0 . . ?
C5 N9 H9B 120.0 . . ?
H9A N9 H9B 120.0 . . ?
N10 C5 N9 119.91(18) . . ?
N10 C5 N8 120.86(19) . . ?
N9 C5 N8 119.2(2) . . ?
C7 O8 C8 117.4(2) . . ?
O7 C7 O8 123.2(3) . . ?
O7 C7 C6 124.2(3) . . ?
O8 C7 C6 112.7(2) . . ?
C7 C6 H6A 109.5 . . ?
C7 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C7 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
O8 C8 C9 108.6(3) . . ?
O8 C8 H8C 110.0 . . ?
C9 C8 H8C 110.0 . . ?
O8 C8 H8D 110.0 . . ?
C9 C8 H8D 110.0 . . ?
H8C C8 H8D 108.4 . . ?
C8 C9 H9C 109.5 . . ?
C8 C9 H9D 109.5 . . ?
H9C C9 H9D 109.5 . . ?
C8 C9 H9E 109.5 . . ?
H9C C9 H9E 109.5 . . ?
H9D C9 H9E 109.5 . . ?

_refine_diff_density_max         0.190
_refine_diff_density_min         -0.245
_refine_diff_density_rms         0.046

_shelxl_version_number           2014-3

####################################################################### 
# 
# 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_BO2513-1
_database_code_depnum_ccdc_archive 'CCDC 1565965'
_audit_update_record             
;
2017-10-15 deposited with the CCDC.
2018-01-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C8 H8 N7 Na O8'
_chemical_formula_weight         353.20

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'
Na Na 0.0362 0.0249 '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                   18.955(4)
_cell_length_b                   9.9608(18)
_cell_length_c                   15.930(3)
_cell_angle_alpha                90
_cell_angle_beta                 111.912(2)
_cell_angle_gamma                90
_cell_volume                     2790.5(10)
_cell_formula_units_Z            8
_cell_measurement_temperature    153(2)
_cell_measurement_reflns_used    8256
_cell_measurement_theta_min      2.35
_cell_measurement_theta_max      29.72

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.681
_exptl_crystal_F_000             1440
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.370
_exptl_crystal_size_mid          0.260
_exptl_crystal_size_min          0.170
_exptl_absorpt_coefficient_mu    0.175
_shelx_estimated_absorpt_T_min   0.938
_shelx_estimated_absorpt_T_max   0.971
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      153(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  CCD
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            24352
_diffrn_reflns_av_unetI/netI     0.0337
_diffrn_reflns_av_R_equivalents  0.0291
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.350
_diffrn_reflns_theta_max         29.140
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             7478
_reflns_number_gt                6311
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0557P)²+0.0888P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         7478
_refine_ls_number_parameters     433
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0616
_refine_ls_R_factor_gt           0.0485
_refine_ls_wR_factor_ref         0.1217
_refine_ls_wR_factor_gt          0.1139
_refine_ls_goodness_of_fit_ref   1.129
_refine_ls_restrained_S_all      1.129
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.001

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
Na1 Na 0.38421(3) 0.77142(6) 0.74265(4) 0.02367(14) Uani 1 1 d . . . . .
Na2 Na 0.10962(3) 0.29057(6) 0.75829(4) 0.02489(14) Uani 1 1 d . . . . .
O1 O 0.42249(6) 0.96033(11) 0.60477(7) 0.0310(3) Uani 1 1 d . . . . .
O2 O 0.56392(7) 0.90189(11) 0.90360(7) 0.0338(3) Uani 1 1 d . . . . .
O3 O 0.46195(8) 1.22333(13) 0.43468(8) 0.0444(3) Uani 1 1 d . . . . .
O4 O 0.56141(7) 1.27362(12) 0.55363(8) 0.0384(3) Uani 1 1 d . . . . .
O5 O 0.70575(7) 1.25686(11) 0.94082(8) 0.0346(3) Uani 1 1 d . . . . .
O6 O 0.72637(7) 1.14814(13) 1.06589(8) 0.0402(3) Uani 1 1 d . . . . .
O7 O 0.07066(7) -0.11803(11) 0.87797(9) 0.0387(3) Uani 1 1 d . . . . .
O8 O -0.06810(7) -0.02156(12) 0.58266(9) 0.0403(3) Uani 1 1 d . . . . .
O9 O 0.23017(7) 0.10938(13) 1.06018(8) 0.0426(3) Uani 1 1 d . . . . .
O10 O 0.19466(7) 0.25762(11) 0.95220(8) 0.0369(3) Uani 1 1 d . . . . .
O11 O 0.06046(7) 0.33117(14) 0.56324(9) 0.0478(3) Uani 1 1 d . . . . .
O12 O -0.02739(9) 0.27576(17) 0.43465(9) 0.0612(4) Uani 1 1 d . . . . .
O13 O 0.31940(6) 0.97896(11) 0.72011(7) 0.0308(3) Uani 1 1 d . . . . .
O14 O 0.22199(6) 1.18609(10) 0.73648(7) 0.0283(2) Uani 1 1 d . . . . .
O16 O 0.17312(6) 0.49861(11) 0.79795(8) 0.0314(3) Uani 1 1 d . . . . .
O15 O 0.28133(6) 0.64925(12) 0.75446(8) 0.0373(3) Uani 1 1 d . . . . .
N1 N 0.42154(7) 1.03780(14) 0.52980(9) 0.0306(3) Uani 1 1 d . . . . .
N2 N 0.51761(6) 1.10698(12) 0.65834(8) 0.0221(3) Uani 1 1 d . . . . .
N3 N 0.49276(7) 0.93834(12) 0.75504(8) 0.0266(3) Uani 1 1 d . . . . .
N4 N 0.59285(6) 1.08879(12) 0.84721(8) 0.0226(3) Uani 1 1 d . . . . .
N5 N 0.62307(8) 0.96424(14) 0.97570(9) 0.0334(3) Uani 1 1 d . . . . .
N6 N 0.50217(8) 1.21309(13) 0.51477(9) 0.0295(3) Uani 1 1 d . . . . .
N7 N 0.69358(7) 1.16546(13) 0.98467(8) 0.0274(3) Uani 1 1 d . . . . .
N8 N 0.12646(8) -0.06223(14) 0.95567(10) 0.0373(3) Uani 1 1 d . . . . .
N9 N 0.09666(7) 0.08391(12) 0.83741(8) 0.0253(3) Uani 1 1 d . . . . .
N10 N 0.00038(7) -0.06240(13) 0.73195(10) 0.0319(3) Uani 1 1 d . . . . .
N11 N 0.02386(7) 0.12595(13) 0.64893(8) 0.0259(3) Uani 1 1 d . . . . .
N12 N -0.06978(8) 0.07152(16) 0.51471(10) 0.0405(4) Uani 1 1 d . . . . .
N13 N 0.19149(7) 0.14703(13) 0.98378(9) 0.0296(3) Uani 1 1 d . . . . .
N14 N 0.00744(9) 0.26149(17) 0.51589(10) 0.0395(4) Uani 1 1 d . . . . .
C1 C 0.47850(8) 1.11778(14) 0.56905(10) 0.0233(3) Uani 1 1 d . . . . .
C2 C 0.48146(8) 1.00533(14) 0.67881(10) 0.0227(3) Uani 1 1 d . . . . .
C3 C 0.54830(8) 0.98161(14) 0.82887(10) 0.0238(3) Uani 1 1 d . . . . .
C4 C 0.63462(8) 1.06944(15) 0.93508(10) 0.0247(3) Uani 1 1 d . . . . .
C5 C 0.13661(8) 0.05239(15) 0.92429(10) 0.0263(3) Uani 1 1 d . . . . .
C6 C 0.05441(8) -0.02589(15) 0.80964(11) 0.0275(3) Uani 1 1 d . . . . .
C7 C -0.01102(8) 0.01639(16) 0.66092(11) 0.0281(3) Uani 1 1 d . . . . .
C8 C -0.01467(9) 0.15005(17) 0.56059(10) 0.0299(3) Uani 1 1 d . . . . .
C9 C 0.34357(9) 1.07167(18) 0.79395(11) 0.0358(4) Uani 1 1 d . . . . .
H9A H 0.3699 1.1483 0.7789 0.043 Uiso 1 1 calc R U . . .
H9B H 0.3799 1.0269 0.8484 0.043 Uiso 1 1 calc R U . . .
C10 C 0.27649(10) 1.12215(19) 0.81350(11) 0.0383(4) Uani 1 1 d . . . . .
H10A H 0.2521 1.0459 0.8321 0.046 Uiso 1 1 calc R U . . .
H10B H 0.2943 1.1867 0.8644 0.046 Uiso 1 1 calc R U . . .
C11 C 0.19960(9) 1.09595(17) 0.66115(11) 0.0319(4) Uani 1 1 d . . . . .
H11A H 0.1642 1.1426 0.6069 0.038 Uiso 1 1 calc R U . . .
H11B H 0.1723 1.0186 0.6739 0.038 Uiso 1 1 calc R U . . .
C12 C 0.26719(9) 1.04576(17) 0.64235(10) 0.0331(4) Uani 1 1 d . . . . .
H12A H 0.2499 0.9829 0.5905 0.040 Uiso 1 1 calc R U . . .
H12B H 0.2929 1.1223 0.6261 0.040 Uiso 1 1 calc R U . . .
C13 C 0.20218(9) 0.65577(18) 0.69992(11) 0.0349(4) Uani 1 1 d . . . . .
H13A H 0.1900 0.5891 0.6504 0.042 Uiso 1 1 calc R U . . .
H13B H 0.1897 0.7461 0.6724 0.042 Uiso 1 1 calc R U . . .
C14 C 0.15499(9) 0.62787(16) 0.75572(12) 0.0337(4) Uani 1 1 d . . . . .
H14A H 0.1646 0.6980 0.8027 0.040 Uiso 1 1 calc R U . . .
H14B H 0.1004 0.6309 0.7165 0.040 Uiso 1 1 calc R U . . .
C15 C 0.25230(9) 0.49696(18) 0.85406(11) 0.0346(4) Uani 1 1 d . . . . .
H15A H 0.2658 0.4092 0.8852 0.041 Uiso 1 1 calc R U . . .
H15B H 0.2632 0.5680 0.9007 0.041 Uiso 1 1 calc R U . . .
C16 C 0.29888(9) 0.52003(17) 0.79721(13) 0.0379(4) Uani 1 1 d . . . . .
H16A H 0.3536 0.5156 0.8357 0.045 Uiso 1 1 calc R U . . .
H16B H 0.2878 0.4491 0.7505 0.045 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Na1 O13 2.3627(12) . ?
Na1 O15 2.3649(13) . ?
Na1 N4 2.4520(13) 2_646 ?
Na1 N2 2.5384(13) 2_646 ?
Na1 N3 2.5950(14) . ?
Na1 O5 2.7841(14) 2_646 ?
Na1 O4 3.0164(15) 2_646 ?
Na2 O16 2.3611(12) . ?
Na2 N9 2.4734(14) . ?
Na2 N11 2.5005(14) . ?
Na2 O14 2.5085(12) 1_545 ?
Na2 N10 2.5998(14) 2_556 ?
Na2 O11 2.9199(16) . ?
Na2 O10 2.9209(14) . ?
O1 C2 1.3629(17) . ?
O1 N1 1.4164(17) . ?
O2 C3 1.3684(17) . ?
O2 N5 1.4145(17) . ?
O3 N6 1.2221(17) . ?
O4 N6 1.2202(18) . ?
O4 Na1 3.0163(15) 2_656 ?
O5 N7 1.2209(16) . ?
O5 Na1 2.7842(14) 2_656 ?
O6 N7 1.2207(16) . ?
O7 C6 1.3681(19) . ?
O7 N8 1.4080(18) . ?
O8 C7 1.3641(18) . ?
O8 N12 1.417(2) . ?
O9 N13 1.2220(17) . ?
O10 N13 1.2217(17) . ?
O11 N14 1.223(2) . ?
O12 N14 1.2220(19) . ?
O13 C12 1.4289(18) . ?
O13 C9 1.4298(18) . ?
O14 C10 1.4256(18) . ?
O14 C11 1.4305(18) . ?
O14 Na2 2.5085(12) 1_565 ?
O16 C15 1.4320(18) . ?
O16 C14 1.4338(19) . ?
O15 C13 1.4273(18) . ?
O15 C16 1.4359(19) . ?
N1 C1 1.2990(19) . ?
N2 C2 1.3295(18) . ?
N2 C1 1.3407(18) . ?
N2 Na1 2.5384(13) 2_656 ?
N3 C3 1.3241(18) . ?
N3 C2 1.3310(19) . ?
N4 C3 1.3244(18) . ?
N4 C4 1.3403(18) . ?
N4 Na1 2.4521(14) 2_656 ?
N5 C4 1.2925(19) . ?
N6 C1 1.4629(19) . ?
N7 C4 1.4590(19) . ?
N8 C5 1.289(2) . ?
N9 C6 1.3299(19) . ?
N9 C5 1.3435(19) . ?
N10 C7 1.327(2) . ?
N10 C6 1.329(2) . ?
N10 Na2 2.5997(15) 2_546 ?
N11 C7 1.326(2) . ?
N11 C8 1.3434(19) . ?
N12 C8 1.291(2) . ?
N13 C5 1.461(2) . ?
N14 C8 1.462(2) . ?
C9 C10 1.504(2) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.506(2) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.504(2) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.500(2) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?

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
O13 Na1 O15 93.72(5) . . ?
O13 Na1 N4 139.09(5) . 2_646 ?
O15 Na1 N4 89.76(5) . 2_646 ?
O13 Na1 N2 151.42(5) . 2_646 ?
O15 Na1 N2 93.08(4) . 2_646 ?
N4 Na1 N2 68.61(4) 2_646 2_646 ?
O13 Na1 N3 78.66(5) . . ?
O15 Na1 N3 167.85(5) . . ?
N4 Na1 N3 102.20(4) 2_646 . ?
N2 Na1 N3 89.40(4) 2_646 . ?
O13 Na1 O5 78.81(4) . 2_646 ?
O15 Na1 O5 81.75(4) . 2_646 ?
N4 Na1 O5 61.38(4) 2_646 2_646 ?
N2 Na1 O5 129.68(4) 2_646 2_646 ?
N3 Na1 O5 105.71(4) . 2_646 ?
O13 Na1 O4 96.13(4) . 2_646 ?
O15 Na1 O4 83.05(4) . 2_646 ?
N4 Na1 O4 124.73(4) 2_646 2_646 ?
N2 Na1 O4 57.27(4) 2_646 2_646 ?
N3 Na1 O4 88.32(4) . 2_646 ?
O5 Na1 O4 163.61(4) 2_646 2_646 ?
O16 Na2 N9 137.03(5) . . ?
O16 Na2 N11 153.63(5) . . ?
N9 Na2 N11 69.32(5) . . ?
O16 Na2 O14 91.54(4) . 1_545 ?
N9 Na2 O14 88.64(4) . 1_545 ?
N11 Na2 O14 89.79(4) . 1_545 ?
O16 Na2 N10 80.19(4) . 2_556 ?
N9 Na2 N10 101.77(5) . 2_556 ?
N11 Na2 N10 94.80(5) . 2_556 ?
O14 Na2 N10 169.54(5) 1_545 2_556 ?
O16 Na2 O11 95.25(4) . . ?
N9 Na2 O11 127.20(5) . . ?
N11 Na2 O11 58.88(4) . . ?
O14 Na2 O11 81.97(4) 1_545 . ?
N10 Na2 O11 92.35(4) 2_556 . ?
O16 Na2 O10 77.91(4) . . ?
N9 Na2 O10 59.21(4) . . ?
N11 Na2 O10 128.45(4) . . ?
O14 Na2 O10 86.44(4) 1_545 . ?
N10 Na2 O10 97.96(5) 2_556 . ?
O11 Na2 O10 166.41(4) . . ?
C2 O1 N1 107.38(11) . . ?
C3 O2 N5 107.47(11) . . ?
N6 O4 Na1 115.00(9) . 2_656 ?
N7 O5 Na1 117.84(9) . 2_656 ?
C6 O7 N8 107.87(11) . . ?
C7 O8 N12 107.52(12) . . ?
N13 O10 Na2 116.38(9) . . ?
N14 O11 Na2 116.12(10) . . ?
C12 O13 C9 108.55(12) . . ?
C12 O13 Na1 133.78(9) . . ?
C9 O13 Na1 116.82(9) . . ?
C10 O14 C11 109.54(12) . . ?
C10 O14 Na2 116.50(9) . 1_565 ?
C11 O14 Na2 112.04(8) . 1_565 ?
C15 O16 C14 108.37(11) . . ?
C15 O16 Na2 117.89(9) . . ?
C14 O16 Na2 130.81(9) . . ?
C13 O15 C16 109.54(12) . . ?
C13 O15 Na1 129.70(9) . . ?
C16 O15 Na1 116.55(9) . . ?
C1 N1 O1 100.45(11) . . ?
C2 N2 C1 100.95(12) . . ?
C2 N2 Na1 131.65(10) . 2_656 ?
C1 N2 Na1 126.46(10) . 2_656 ?
C3 N3 C2 116.81(12) . . ?
C3 N3 Na1 128.40(10) . . ?
C2 N3 Na1 113.51(9) . . ?
C3 N4 C4 101.19(12) . . ?
C3 N4 Na1 134.96(10) . 2_656 ?
C4 N4 Na1 123.51(10) . 2_656 ?
C4 N5 O2 100.40(12) . . ?
O4 N6 O3 125.87(14) . . ?
O4 N6 C1 116.61(13) . . ?
O3 N6 C1 117.51(14) . . ?
O6 N7 O5 125.57(13) . . ?
O6 N7 C4 117.74(13) . . ?
O5 N7 C4 116.69(12) . . ?
C5 N8 O7 100.40(13) . . ?
C6 N9 C5 100.86(13) . . ?
C6 N9 Na2 132.60(10) . . ?
C5 N9 Na2 126.47(10) . . ?
C7 N10 C6 117.12(13) . . ?
C7 N10 Na2 120.34(10) . 2_546 ?
C6 N10 Na2 117.06(10) . 2_546 ?
C7 N11 C8 101.10(13) . . ?
C7 N11 Na2 131.97(11) . . ?
C8 N11 Na2 124.80(11) . . ?
C8 N12 O8 100.44(13) . . ?
O10 N13 O9 125.69(14) . . ?
O10 N13 C5 116.57(13) . . ?
O9 N13 C5 117.74(13) . . ?
O12 N14 O11 125.60(17) . . ?
O12 N14 C8 117.67(16) . . ?
O11 N14 C8 116.72(14) . . ?
N1 C1 N2 119.51(14) . . ?
N1 C1 N6 119.77(13) . . ?
N2 C1 N6 120.61(13) . . ?
N2 C2 N3 133.11(13) . . ?
N2 C2 O1 111.68(13) . . ?
N3 C2 O1 115.18(12) . . ?
N3 C3 N4 133.51(14) . . ?
N3 C3 O2 115.22(13) . . ?
N4 C3 O2 111.27(12) . . ?
N5 C4 N4 119.67(14) . . ?
N5 C4 N7 119.94(13) . . ?
N4 C4 N7 120.39(13) . . ?
N8 C5 N9 119.87(15) . . ?
N8 C5 N13 119.55(14) . . ?
N9 C5 N13 120.58(13) . . ?
N10 C6 N9 133.93(15) . . ?
N10 C6 O7 115.07(13) . . ?
N9 C6 O7 110.99(13) . . ?
N11 C7 N10 132.70(14) . . ?
N11 C7 O8 111.37(14) . . ?
N10 C7 O8 115.90(14) . . ?
N12 C8 N11 119.57(16) . . ?
N12 C8 N14 120.17(15) . . ?
N11 C8 N14 120.22(14) . . ?
O13 C9 C10 110.50(13) . . ?
O13 C9 H9A 109.6 . . ?
C10 C9 H9A 109.6 . . ?
O13 C9 H9B 109.6 . . ?
C10 C9 H9B 109.6 . . ?
H9A C9 H9B 108.1 . . ?
O14 C10 C9 111.61(13) . . ?
O14 C10 H10A 109.3 . . ?
C9 C10 H10A 109.3 . . ?
O14 C10 H10B 109.3 . . ?
C9 C10 H10B 109.3 . . ?
H10A C10 H10B 108.0 . . ?
O14 C11 C12 111.54(12) . . ?
O14 C11 H11A 109.3 . . ?
C12 C11 H11A 109.3 . . ?
O14 C11 H11B 109.3 . . ?
C12 C11 H11B 109.3 . . ?
H11A C11 H11B 108.0 . . ?
O13 C12 C11 110.35(13) . . ?
O13 C12 H12A 109.6 . . ?
C11 C12 H12A 109.6 . . ?
O13 C12 H12B 109.6 . . ?
C11 C12 H12B 109.6 . . ?
H12A C12 H12B 108.1 . . ?
O15 C13 C14 110.72(13) . . ?
O15 C13 H13A 109.5 . . ?
C14 C13 H13A 109.5 . . ?
O15 C13 H13B 109.5 . . ?
C14 C13 H13B 109.5 . . ?
H13A C13 H13B 108.1 . . ?
O16 C14 C13 110.61(13) . . ?
O16 C14 H14A 109.5 . . ?
C13 C14 H14A 109.5 . . ?
O16 C14 H14B 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 108.1 . . ?
O16 C15 C16 109.72(13) . . ?
O16 C15 H15A 109.7 . . ?
C16 C15 H15A 109.7 . . ?
O16 C15 H15B 109.7 . . ?
C16 C15 H15B 109.7 . . ?
H15A C15 H15B 108.2 . . ?
O15 C16 C15 109.83(14) . . ?
O15 C16 H16A 109.7 . . ?
C15 C16 H16A 109.7 . . ?
O15 C16 H16B 109.7 . . ?
C15 C16 H16B 109.7 . . ?
H16A C16 H16B 108.2 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C2 O1 N1 C1 -0.69(14) . . . . ?
C3 O2 N5 C4 -0.32(16) . . . . ?
Na1 O4 N6 O3 163.95(12) 2_656 . . . ?
Na1 O4 N6 C1 -17.46(16) 2_656 . . . ?
Na1 O5 N7 O6 -177.53(12) 2_656 . . . ?
Na1 O5 N7 C4 2.40(16) 2_656 . . . ?
C6 O7 N8 C5 -0.61(16) . . . . ?
C7 O8 N12 C8 0.18(15) . . . . ?
Na2 O10 N13 O9 170.53(12) . . . . ?
Na2 O10 N13 C5 -9.29(16) . . . . ?
Na2 O11 N14 O12 169.83(13) . . . . ?
Na2 O11 N14 C8 -11.57(17) . . . . ?
O1 N1 C1 N2 -0.13(17) . . . . ?
O1 N1 C1 N6 176.23(12) . . . . ?
C2 N2 C1 N1 0.88(17) . . . . ?
Na1 N2 C1 N1 -169.00(10) 2_656 . . . ?
C2 N2 C1 N6 -175.44(12) . . . . ?
Na1 N2 C1 N6 14.68(18) 2_656 . . . ?
O4 N6 C1 N1 -171.26(14) . . . . ?
O3 N6 C1 N1 7.5(2) . . . . ?
O4 N6 C1 N2 5.1(2) . . . . ?
O3 N6 C1 N2 -176.23(13) . . . . ?
C1 N2 C2 N3 176.51(16) . . . . ?
Na1 N2 C2 N3 -14.4(2) 2_656 . . . ?
C1 N2 C2 O1 -1.28(15) . . . . ?
Na1 N2 C2 O1 167.82(9) 2_656 . . . ?
C3 N3 C2 N2 4.0(2) . . . . ?
Na1 N3 C2 N2 172.20(13) . . . . ?
C3 N3 C2 O1 -178.23(12) . . . . ?
Na1 N3 C2 O1 -10.07(15) . . . . ?
N1 O1 C2 N2 1.31(16) . . . . ?
N1 O1 C2 N3 -176.91(12) . . . . ?
C2 N3 C3 N4 7.9(2) . . . . ?
Na1 N3 C3 N4 -158.22(13) . . . . ?
C2 N3 C3 O2 -172.99(13) . . . . ?
Na1 N3 C3 O2 20.90(19) . . . . ?
C4 N4 C3 N3 178.81(16) . . . . ?
Na1 N4 C3 N3 -8.0(3) 2_656 . . . ?
C4 N4 C3 O2 -0.33(15) . . . . ?
Na1 N4 C3 O2 172.83(10) 2_656 . . . ?
N5 O2 C3 N3 -178.88(12) . . . . ?
N5 O2 C3 N4 0.43(16) . . . . ?
O2 N5 C4 N4 0.13(18) . . . . ?
O2 N5 C4 N7 -179.10(12) . . . . ?
C3 N4 C4 N5 0.12(18) . . . . ?
Na1 N4 C4 N5 -174.08(11) 2_656 . . . ?
C3 N4 C4 N7 179.34(13) . . . . ?
Na1 N4 C4 N7 5.14(18) 2_656 . . . ?
O6 N7 C4 N5 -5.7(2) . . . . ?
O5 N7 C4 N5 174.33(14) . . . . ?
O6 N7 C4 N4 175.05(13) . . . . ?
O5 N7 C4 N4 -4.9(2) . . . . ?
O7 N8 C5 N9 -0.04(18) . . . . ?
O7 N8 C5 N13 179.83(12) . . . . ?
C6 N9 C5 N8 0.67(18) . . . . ?
Na2 N9 C5 N8 -176.64(11) . . . . ?
C6 N9 C5 N13 -179.20(13) . . . . ?
Na2 N9 C5 N13 3.48(19) . . . . ?
O10 N13 C5 N8 -174.82(14) . . . . ?
O9 N13 C5 N8 5.3(2) . . . . ?
O10 N13 C5 N9 5.1(2) . . . . ?
O9 N13 C5 N9 -174.78(13) . . . . ?
C7 N10 C6 N9 9.2(3) . . . . ?
Na2 N10 C6 N9 -144.87(15) 2_546 . . . ?
C7 N10 C6 O7 -172.23(13) . . . . ?
Na2 N10 C6 O7 33.73(16) 2_546 . . . ?
C5 N9 C6 N10 177.62(17) . . . . ?
Na2 N9 C6 N10 -5.3(3) . . . . ?
C5 N9 C6 O7 -1.02(16) . . . . ?
Na2 N9 C6 O7 176.05(10) . . . . ?
N8 O7 C6 N10 -177.83(13) . . . . ?
N8 O7 C6 N9 1.08(17) . . . . ?
C8 N11 C7 N10 177.50(17) . . . . ?
Na2 N11 C7 N10 -19.0(3) . . . . ?
C8 N11 C7 O8 -0.38(16) . . . . ?
Na2 N11 C7 O8 163.08(9) . . . . ?
C6 N10 C7 N11 3.8(3) . . . . ?
Na2 N10 C7 N11 156.97(14) 2_546 . . . ?
C6 N10 C7 O8 -178.38(13) . . . . ?
Na2 N10 C7 O8 -25.23(17) 2_546 . . . ?
N12 O8 C7 N11 0.14(16) . . . . ?
N12 O8 C7 N10 -178.13(13) . . . . ?
O8 N12 C8 N11 -0.48(18) . . . . ?
O8 N12 C8 N14 177.27(13) . . . . ?
C7 N11 C8 N12 0.56(18) . . . . ?
Na2 N11 C8 N12 -164.49(11) . . . . ?
C7 N11 C8 N14 -177.18(13) . . . . ?
Na2 N11 C8 N14 17.76(19) . . . . ?
O12 N14 C8 N12 -0.7(2) . . . . ?
O11 N14 C8 N12 -179.44(15) . . . . ?
O12 N14 C8 N11 177.01(15) . . . . ?
O11 N14 C8 N11 -1.7(2) . . . . ?
C12 O13 C9 C10 59.31(18) . . . . ?
Na1 O13 C9 C10 -129.77(12) . . . . ?
C11 O14 C10 C9 55.39(19) . . . . ?
Na2 O14 C10 C9 -176.16(11) 1_565 . . . ?
O13 C9 C10 O14 -58.5(2) . . . . ?
C10 O14 C11 C12 -55.45(18) . . . . ?
Na2 O14 C11 C12 173.67(11) 1_565 . . . ?
C9 O13 C12 C11 -59.32(17) . . . . ?
Na1 O13 C12 C11 131.93(12) . . . . ?
O14 C11 C12 O13 58.52(18) . . . . ?
C16 O15 C13 C14 56.95(18) . . . . ?
Na1 O15 C13 C14 -147.40(12) . . . . ?
C15 O16 C14 C13 59.12(17) . . . . ?
Na2 O16 C14 C13 -100.60(14) . . . . ?
O15 C13 C14 O16 -57.95(18) . . . . ?
C14 O16 C15 C16 -60.85(17) . . . . ?
Na2 O16 C15 C16 101.88(13) . . . . ?
C13 O15 C16 C15 -58.68(18) . . . . ?
Na1 O15 C16 C15 142.10(11) . . . . ?
O16 C15 C16 O15 61.38(18) . . . . ?

_refine_diff_density_max         0.240
_refine_diff_density_min         -0.227
_refine_diff_density_rms         0.047

_shelxl_version_number           2014-3

####################################################################### 
# 
# 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 1565968'
_audit_update_record             
;
2017-10-15 deposited with the CCDC.
2018-01-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C8 H8 N9 Na O8'
_chemical_formula_weight         381.22

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Na Na 0.0362 0.0249 '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+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'

_cell_length_a                   9.438(2)
_cell_length_b                   34.981(8)
_cell_length_c                   9.410(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3106.7(12)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4981
_cell_measurement_theta_min      2.48
_cell_measurement_theta_max      27.36

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.630
_exptl_crystal_F_000             1552
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.167
_shelx_estimated_absorpt_T_min   0.952
_shelx_estimated_absorpt_T_max   0.983
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  CCD
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            31927
_diffrn_reflns_av_unetI/netI     0.0327
_diffrn_reflns_av_R_equivalents  0.0550
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -46
_diffrn_reflns_limit_k_max       46
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         1.164
_diffrn_reflns_theta_max         28.692
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.968
_diffrn_measured_fraction_theta_full 0.978
_diffrn_reflns_Laue_measured_fraction_max 0.968
_diffrn_reflns_Laue_measured_fraction_full 0.978
_diffrn_reflns_point_group_measured_fraction_max 0.968
_diffrn_reflns_point_group_measured_fraction_full 0.978
_reflns_number_total             3879
_reflns_number_gt                2741
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0324P)²+5.0076P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3879
_refine_ls_number_parameters     235
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1033
_refine_ls_R_factor_gt           0.0762
_refine_ls_wR_factor_ref         0.1719
_refine_ls_wR_factor_gt          0.1604
_refine_ls_goodness_of_fit_ref   1.105
_refine_ls_restrained_S_all      1.105
_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 0.4781(3) 0.06540(9) 0.7165(3) 0.0472(7) Uani 1 1 d . . . . .
C2 C 0.4558(3) 0.19016(9) 0.7338(3) 0.0491(8) Uani 1 1 d . . . . .
C3 C 0.3684(4) 0.02292(9) 0.6161(3) 0.0481(8) Uani 1 1 d . . . . .
C4 C 0.3421(3) 0.23234(9) 0.6332(4) 0.0495(8) Uani 1 1 d . . . . .
C5 C 0.4476(4) 0.10152(14) 0.1305(4) 0.0758(13) Uani 1 1 d . . . . .
H5A H 0.4566 0.0784 0.0742 0.091 Uiso 1 1 calc R U . . .
H5B H 0.3725 0.1169 0.0894 0.091 Uiso 1 1 calc R U . . .
C6 C 0.4094(4) 0.09123(10) 0.2777(4) 0.0635(10) Uani 1 1 d . . . . .
H6A H 0.3189 0.0781 0.2778 0.076 Uiso 1 1 calc R U . . .
H6B H 0.4801 0.0739 0.3158 0.076 Uiso 1 1 calc R U . . .
C7 C 0.5287(4) 0.14486(14) 0.3592(4) 0.0839(15) Uani 1 1 d . . . . .
H7A H 0.6038 0.1297 0.4011 0.101 Uiso 1 1 calc R U . . .
H7B H 0.5193 0.1681 0.4148 0.101 Uiso 1 1 calc R U . . .
C8 C 0.5683(5) 0.15499(10) 0.2128(5) 0.0742(13) Uani 1 1 d . . . . .
H8A H 0.4985 0.1725 0.1741 0.089 Uiso 1 1 calc R U . . .
H8B H 0.6592 0.1679 0.2135 0.089 Uiso 1 1 calc R U . . .
N1 N 0.4700(3) 0.12783(7) 0.7328(3) 0.0459(6) Uani 1 1 d . . . . .
N2 N 0.5390(3) 0.09715(8) 0.7732(3) 0.0508(7) Uani 1 1 d . . . . .
N3 N 0.5247(3) 0.15900(8) 0.7854(3) 0.0519(7) Uani 1 1 d . . . . .
N4 N 0.3606(3) 0.19393(7) 0.6344(3) 0.0454(6) Uani 1 1 d . . . . .
N5 N 0.4167(4) 0.25296(9) 0.7221(4) 0.0721(9) Uani 1 1 d . . . . .
N6 N 0.3673(3) 0.06122(7) 0.6324(3) 0.0451(6) Uani 1 1 d . . . . .
N7 N 0.4646(4) 0.00264(9) 0.6780(3) 0.0675(9) Uani 1 1 d . . . . .
N8 N 0.2634(4) 0.00358(10) 0.5262(4) 0.0656(9) Uani 1 1 d . . . . .
N9 N 0.2472(3) 0.25155(10) 0.5349(4) 0.0659(9) Uani 1 1 d . . . . .
O1 O 0.2657(4) -0.03125(9) 0.5243(4) 0.1043(12) Uani 1 1 d . . . . .
O2 O 0.1862(4) 0.02364(10) 0.4574(3) 0.0873(10) Uani 1 1 d . . . . .
O3 O 0.1848(4) 0.23145(10) 0.4536(4) 0.0933(10) Uani 1 1 d . . . . .
O4 O 0.2399(4) 0.28639(9) 0.5391(4) 0.1069(12) Uani 1 1 d . . . . .
O5 O 0.4948(3) 0.22401(7) 0.7921(3) 0.0682(7) Uani 1 1 d . . . . .
O6 O 0.5415(3) 0.03203(7) 0.7470(3) 0.0645(7) Uani 1 1 d . . . . .
O7 O 0.4004(2) 0.12412(7) 0.3657(2) 0.0543(6) Uani 1 1 d . . . . .
O8 O 0.5769(2) 0.12225(7) 0.1251(2) 0.0533(6) Uani 1 1 d . . . . .
Na1 Na 0.24002(11) 0.12562(3) 0.56283(11) 0.0406(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 N6 1.320(4) . ?
C1 O6 1.343(4) . ?
C1 N2 1.360(4) . ?
C2 N4 1.304(4) . ?
C2 O5 1.356(4) . ?
C2 N3 1.359(4) . ?
C3 N7 1.291(4) . ?
C3 N6 1.349(4) . ?
C3 N8 1.468(5) . ?
C4 N5 1.310(4) . ?
C4 N4 1.355(4) . ?
C4 N9 1.452(5) . ?
C5 O8 1.420(4) . ?
C5 C6 1.476(5) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 O7 1.420(4) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 O7 1.413(4) . ?
C7 C8 1.471(6) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 O8 1.414(4) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
N1 N3 1.304(3) . ?
N1 N2 1.312(4) . ?
N2 Na1 2.640(3) 6_657 ?
N3 Na1 2.744(3) 6_657 ?
N5 O5 1.415(4) . ?
N7 O6 1.416(4) . ?
N8 O2 1.201(5) . ?
N8 O1 1.219(4) . ?
N9 O3 1.194(4) . ?
N9 O4 1.221(4) . ?
O8 Na1 2.348(2) 6_656 ?
Na1 O8 2.348(2) 6_556 ?
Na1 N2 2.640(3) 6_557 ?
Na1 N3 2.744(3) 6_557 ?

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
N6 C1 O6 112.6(3) . . ?
N6 C1 N2 131.4(3) . . ?
O6 C1 N2 116.0(3) . . ?
N4 C2 O5 112.9(3) . . ?
N4 C2 N3 131.8(3) . . ?
O5 C2 N3 115.2(3) . . ?
N7 C3 N6 120.0(3) . . ?
N7 C3 N8 118.8(3) . . ?
N6 C3 N8 121.2(3) . . ?
N5 C4 N4 118.1(3) . . ?
N5 C4 N9 118.9(3) . . ?
N4 C4 N9 122.9(3) . . ?
O8 C5 C6 111.6(3) . . ?
O8 C5 H5A 109.3 . . ?
C6 C5 H5A 109.3 . . ?
O8 C5 H5B 109.3 . . ?
C6 C5 H5B 109.3 . . ?
H5A C5 H5B 108.0 . . ?
O7 C6 C5 111.4(3) . . ?
O7 C6 H6A 109.4 . . ?
C5 C6 H6A 109.4 . . ?
O7 C6 H6B 109.4 . . ?
C5 C6 H6B 109.4 . . ?
H6A C6 H6B 108.0 . . ?
O7 C7 C8 112.4(3) . . ?
O7 C7 H7A 109.1 . . ?
C8 C7 H7A 109.1 . . ?
O7 C7 H7B 109.1 . . ?
C8 C7 H7B 109.1 . . ?
H7A C7 H7B 107.8 . . ?
O8 C8 C7 111.5(3) . . ?
O8 C8 H8A 109.3 . . ?
C7 C8 H8A 109.3 . . ?
O8 C8 H8B 109.3 . . ?
C7 C8 H8B 109.3 . . ?
H8A C8 H8B 108.0 . . ?
N3 N1 N2 112.1(3) . . ?
N1 N2 C1 110.2(3) . . ?
N1 N2 Na1 102.58(19) . 6_657 ?
C1 N2 Na1 147.3(2) . 6_657 ?
N1 N3 C2 110.2(3) . . ?
N1 N3 Na1 97.77(19) . 6_657 ?
C2 N3 Na1 151.8(2) . 6_657 ?
C2 N4 C4 101.3(3) . . ?
C4 N5 O5 100.6(3) . . ?
C1 N6 C3 99.9(3) . . ?
C3 N7 O6 99.7(3) . . ?
O2 N8 O1 126.0(4) . . ?
O2 N8 C3 116.8(3) . . ?
O1 N8 C3 117.2(4) . . ?
O3 N9 O4 125.5(4) . . ?
O3 N9 C4 116.1(3) . . ?
O4 N9 C4 118.4(4) . . ?
C2 O5 N5 107.2(3) . . ?
C1 O6 N7 107.8(3) . . ?
C7 O7 C6 109.9(3) . . ?
C8 O8 C5 110.1(3) . . ?
C8 O8 Na1 115.89(19) . 6_656 ?
C5 O8 Na1 128.0(2) . 6_656 ?
O8 Na1 N2 87.12(9) 6_556 6_557 ?
O8 Na1 N3 85.85(9) 6_556 6_557 ?
N2 Na1 N3 47.49(9) 6_557 6_557 ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O8 C5 C6 O7 56.7(5) . . . . ?
O7 C7 C8 O8 -56.0(5) . . . . ?
N3 N1 N2 C1 179.8(3) . . . . ?
N3 N1 N2 Na1 0.4(3) . . . 6_657 ?
N6 C1 N2 N1 -0.1(5) . . . . ?
O6 C1 N2 N1 178.3(3) . . . . ?
N6 C1 N2 Na1 178.8(3) . . . 6_657 ?
O6 C1 N2 Na1 -2.9(5) . . . 6_657 ?
N2 N1 N3 C2 176.2(3) . . . . ?
N2 N1 N3 Na1 -0.4(3) . . . 6_657 ?
N4 C2 N3 N1 -8.5(5) . . . . ?
O5 C2 N3 N1 173.8(3) . . . . ?
N4 C2 N3 Na1 164.3(3) . . . 6_657 ?
O5 C2 N3 Na1 -13.5(6) . . . 6_657 ?
O5 C2 N4 C4 0.2(3) . . . . ?
N3 C2 N4 C4 -177.6(3) . . . . ?
N5 C4 N4 C2 0.1(4) . . . . ?
N9 C4 N4 C2 178.0(3) . . . . ?
N4 C4 N5 O5 -0.3(4) . . . . ?
N9 C4 N5 O5 -178.2(3) . . . . ?
O6 C1 N6 C3 0.6(3) . . . . ?
N2 C1 N6 C3 178.9(3) . . . . ?
N7 C3 N6 C1 -0.2(4) . . . . ?
N8 C3 N6 C1 -178.8(3) . . . . ?
N6 C3 N7 O6 -0.2(4) . . . . ?
N8 C3 N7 O6 178.4(3) . . . . ?
N7 C3 N8 O2 -171.5(3) . . . . ?
N6 C3 N8 O2 7.1(5) . . . . ?
N7 C3 N8 O1 6.1(5) . . . . ?
N6 C3 N8 O1 -175.3(3) . . . . ?
N5 C4 N9 O3 178.0(3) . . . . ?
N4 C4 N9 O3 0.1(5) . . . . ?
N5 C4 N9 O4 -0.3(5) . . . . ?
N4 C4 N9 O4 -178.2(3) . . . . ?
N4 C2 O5 N5 -0.4(4) . . . . ?
N3 C2 O5 N5 177.8(3) . . . . ?
C4 N5 O5 C2 0.4(3) . . . . ?
N6 C1 O6 N7 -0.7(4) . . . . ?
N2 C1 O6 N7 -179.4(3) . . . . ?
C3 N7 O6 C1 0.6(3) . . . . ?
C8 C7 O7 C6 55.2(5) . . . . ?
C5 C6 O7 C7 -55.3(5) . . . . ?
C7 C8 O8 C5 55.0(5) . . . . ?
C7 C8 O8 Na1 -149.9(3) . . . 6_656 ?
C6 C5 O8 C8 -55.8(5) . . . . ?
C6 C5 O8 Na1 153.0(3) . . . 6_656 ?

_refine_diff_density_max         0.287
_refine_diff_density_min         -0.233
_refine_diff_density_rms         0.053

_shelxl_version_number           2014-3

####################################################################### 
# 
# 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_fd-3
_database_code_depnum_ccdc_archive 'CCDC 1565966'
_audit_update_record             
;
2018-01-14 deposited with the CCDC.
2018-01-29 downloaded from the CCDC.
;
_audit_creation_date             2017-10-30
_audit_creation_method           
;
Olex2 1.2-dev
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5356)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '1(C48 N84 Na7 O72 H5), 18.0(H2O), 6.0(H2O)'
_chemical_formula_sum            'C48 H53 N84 Na7 O96'
_chemical_formula_weight         3503.37
_chemical_melting_point          ?
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'
Na Na 0.0362 0.0249 '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'

_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.
;
_space_group_crystal_system      cubic
_space_group_IT_number           203
_space_group_name_H-M_alt        'F d -3'
_space_group_name_Hall           '-F 2uv 2vw 3'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/4, -y+1/4, z'
'-x+1/4, y, -z+1/4'
'x, -y+1/4, -z+1/4'
'z, x, y'
'z, -x+1/4, -y+1/4'
'-z+1/4, -x+1/4, y'
'-z+1/4, x, -y+1/4'
'y, z, x'
'-y+1/4, z, -x+1/4'
'y, -z+1/4, -x+1/4'
'-y+1/4, -z+1/4, x'
'x, y+1/2, z+1/2'
'-x+1/4, -y+3/4, z+1/2'
'-x+1/4, y+1/2, -z+3/4'
'x, -y+3/4, -z+3/4'
'z, x+1/2, y+1/2'
'z, -x+3/4, -y+3/4'
'-z+1/4, -x+3/4, y+1/2'
'-z+1/4, x+1/2, -y+3/4'
'y, z+1/2, x+1/2'
'-y+1/4, z+1/2, -x+3/4'
'y, -z+3/4, -x+3/4'
'-y+1/4, -z+3/4, x+1/2'
'x+1/2, y, z+1/2'
'-x+3/4, -y+1/4, z+1/2'
'-x+3/4, y, -z+3/4'
'x+1/2, -y+1/4, -z+3/4'
'z+1/2, x, y+1/2'
'z+1/2, -x+1/4, -y+3/4'
'-z+3/4, -x+1/4, y+1/2'
'-z+3/4, x, -y+3/4'
'y+1/2, z, x+1/2'
'-y+3/4, z, -x+3/4'
'y+1/2, -z+1/4, -x+3/4'
'-y+3/4, -z+1/4, x+1/2'
'x+1/2, y+1/2, z'
'-x+3/4, -y+3/4, z'
'-x+3/4, y+1/2, -z+1/4'
'x+1/2, -y+3/4, -z+1/4'
'z+1/2, x+1/2, y'
'z+1/2, -x+3/4, -y+1/4'
'-z+3/4, -x+3/4, y'
'-z+3/4, x+1/2, -y+1/4'
'y+1/2, z+1/2, x'
'-y+3/4, z+1/2, -x+1/4'
'y+1/2, -z+3/4, -x+1/4'
'-y+3/4, -z+3/4, x'
'-x, -y, -z'
'x-1/4, y-1/4, -z'
'x-1/4, -y, z-1/4'
'-x, y-1/4, z-1/4'
'-z, -x, -y'
'-z, x-1/4, y-1/4'
'z-1/4, x-1/4, -y'
'z-1/4, -x, y-1/4'
'-y, -z, -x'
'y-1/4, -z, x-1/4'
'-y, z-1/4, x-1/4'
'y-1/4, z-1/4, -x'
'-x, -y+1/2, -z+1/2'
'x-1/4, y+1/4, -z+1/2'
'x-1/4, -y+1/2, z+1/4'
'-x, y+1/4, z+1/4'
'-z, -x+1/2, -y+1/2'
'-z, x+1/4, y+1/4'
'z-1/4, x+1/4, -y+1/2'
'z-1/4, -x+1/2, y+1/4'
'-y, -z+1/2, -x+1/2'
'y-1/4, -z+1/2, x+1/4'
'-y, z+1/4, x+1/4'
'y-1/4, z+1/4, -x+1/2'
'-x+1/2, -y, -z+1/2'
'x+1/4, y-1/4, -z+1/2'
'x+1/4, -y, z+1/4'
'-x+1/2, y-1/4, z+1/4'
'-z+1/2, -x, -y+1/2'
'-z+1/2, x-1/4, y+1/4'
'z+1/4, x-1/4, -y+1/2'
'z+1/4, -x, y+1/4'
'-y+1/2, -z, -x+1/2'
'y+1/4, -z, x+1/4'
'-y+1/2, z-1/4, x+1/4'
'y+1/4, z-1/4, -x+1/2'
'-x+1/2, -y+1/2, -z'
'x+1/4, y+1/4, -z'
'x+1/4, -y+1/2, z-1/4'
'-x+1/2, y+1/4, z-1/4'
'-z+1/2, -x+1/2, -y'
'-z+1/2, x+1/4, y-1/4'
'z+1/4, x+1/4, -y'
'z+1/4, -x+1/2, y-1/4'
'-y+1/2, -z+1/2, -x'
'y+1/4, -z+1/2, x-1/4'
'-y+1/2, z+1/4, x-1/4'
'y+1/4, z+1/4, -x'

_cell_length_a                   37.2002(12)
_cell_length_b                   37.2002(12)
_cell_length_c                   37.2002(12)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     51480(5)
_cell_formula_units_Z            16.00032
_cell_measurement_reflns_used    9805
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      20.65
_cell_measurement_theta_min      2.19
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.191
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.806
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             28305
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.100
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0126
_diffrn_reflns_av_unetI/netI     0.0126
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       44
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       44
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       44
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            11343
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        24.992
_diffrn_reflns_theta_max         24.992
_diffrn_reflns_theta_min         1.816
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3199
_reflns_number_total             3797
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.200
_refine_diff_density_min         -0.155
_refine_diff_density_rms         0.032
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_hydrogen_treatment    undef
_refine_ls_matrix_type           full
_refine_ls_number_parameters     318
_refine_ls_number_reflns         3797
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0607
_refine_ls_R_factor_gt           0.0489
_refine_ls_restrained_S_all      1.089
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0482P)²+97.3811P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1121
_refine_ls_wR_factor_ref         0.1193
_refine_special_details          ?
_olex2_refinement_description    
;
;
_atom_sites_solution_hydrogens   .
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
Na01 Na 0.500000 0.500000 0.500000 0.0360(4) Uani 1 6 d S T P . .
Na02 Na 0.58735(2) 0.46769(3) 0.33754(3) 0.0602(3) Uani 1 1 d . . . . .
O O 0.49398(5) 0.45858(6) 0.41730(4) 0.0674(5) Uani 1 1 d . . . . .
N004 N 0.53925(5) 0.46974(5) 0.38016(5) 0.0508(5) Uani 1 1 d . . . . .
N005 N 0.61256(5) 0.51201(5) 0.29716(5) 0.0547(5) Uani 1 1 d . . . . .
N006 N 0.54205(5) 0.42399(5) 0.32082(5) 0.0532(5) Uani 1 1 d . . . . .
O007 O 0.71131(5) 0.47349(6) 0.33682(6) 0.0815(6) Uani 1 1 d . . . . .
N008 N 0.65246(6) 0.46479(5) 0.34108(5) 0.0581(5) Uani 1 1 d . . . . .
O009 O 0.49412(5) 0.38923(6) 0.31628(5) 0.0816(6) Uani 1 1 d . . . . .
O0AA O 0.58846(6) 0.52051(6) 0.38914(6) 0.0828(6) Uani 1 1 d . . . . .
O1 O 0.59322(6) 0.42931(6) 0.27009(6) 0.0875(6) Uani 1 1 d . . . . .
O00C O 0.64775(6) 0.54363(6) 0.26064(6) 0.0859(6) Uani 1 1 d . . . . .
N00D N 0.56478(6) 0.52023(6) 0.41146(6) 0.0660(6) Uani 1 1 d . . . . .
N00E N 0.49656(6) 0.42222(6) 0.36784(6) 0.0653(6) Uani 1 1 d . . . . .
O2 O 0.62084(7) 0.41715(6) 0.38491(6) 0.0930(7) Uani 1 1 d . . . . .
N00G N 0.51246(6) 0.48841(7) 0.43146(5) 0.0651(6) Uani 1 1 d . . . . .
N00H N 0.56822(7) 0.40959(6) 0.26257(6) 0.0669(6) Uani 1 1 d . . . . .
O00I O 0.56464(6) 0.39332(6) 0.23449(5) 0.0899(7) Uani 1 1 d . . . . .
O3 O 0.54023(6) 0.51400(7) 0.29511(6) 0.0945(7) Uani 1 1 d . . . . .
O00K O 0.54115(6) 0.55803(6) 0.25699(7) 0.0969(7) Uani 1 1 d . . . . .
N00L N 0.67791(6) 0.50829(7) 0.29962(7) 0.0707(6) Uani 1 1 d . . . . .
N00M N 0.65329(8) 0.41858(7) 0.38692(7) 0.0786(7) Uani 1 1 d . . . . .
O00N O 0.56242(6) 0.54080(7) 0.43656(6) 0.1039(8) Uani 1 1 d . . . . .
N00O N 0.55549(7) 0.53520(7) 0.27556(7) 0.0714(6) Uani 1 1 d . . . . .
C00P C 0.53765(6) 0.49229(7) 0.40806(6) 0.0540(6) Uani 1 1 d . . . . .
C00Q C 0.51121(7) 0.44909(7) 0.38629(6) 0.0551(6) Uani 1 1 d . . . . .
N00R N 0.51376(7) 0.38439(7) 0.28410(6) 0.0770(7) Uani 1 1 d . . . . .
C00S C 0.54048(7) 0.40551(6) 0.28980(6) 0.0560(6) Uani 1 1 d . . . . .
O00T O 0.67168(8) 0.40061(7) 0.40715(7) 0.1134(9) Uani 1 1 d . . . . .
C00U C 0.59455(7) 0.53325(7) 0.27453(7) 0.0588(6) Uani 1 1 d . . . . .
N00V N 0.61206(8) 0.55278(7) 0.25202(7) 0.0819(7) Uani 1 1 d . . . . .
C00W C 0.64628(7) 0.51921(7) 0.28808(7) 0.0605(6) Uani 1 1 d . . . . .
N00X N 0.70623(7) 0.44650(8) 0.36276(7) 0.0829(7) Uani 1 1 d . . . . .
C00Y C 0.51238(7) 0.41351(7) 0.33694(7) 0.0572(6) Uani 1 1 d . . . . .
C00Z C 0.67817(7) 0.48358(8) 0.32469(8) 0.0635(7) Uani 1 1 d . . . . .
C010 C 0.67156(8) 0.44383(7) 0.36293(7) 0.0642(7) 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
Na01 N00G 2.627(2) 57_666 ?
Na01 N00G 2.627(2) 49_666 ?
Na01 N00G 2.627(2) 9 ?
Na01 N00G 2.627(2) 53_666 ?
Na01 N00G 2.627(2) 5 ?
Na01 N00G 2.627(2) . ?
Na02 N004 2.392(2) . ?
Na02 N005 2.420(2) . ?
Na02 N006 2.423(2) . ?
Na02 N008 2.428(2) . ?
Na02 O0AA 2.748(2) . ?
Na02 O1 2.895(2) . ?
Na02 O2 2.862(3) . ?
Na02 O3 2.921(3) . ?
O N00G 1.408(3) . ?
O C00Q 1.366(3) . ?
N004 C00P 1.336(3) . ?
N004 C00Q 1.315(3) . ?
N005 C00U 1.335(3) . ?
N005 C00W 1.326(3) . ?
N006 C00S 1.344(3) . ?
N006 C00Y 1.315(3) . ?
O007 N00X 1.405(3) . ?
O007 C00Z 1.366(3) . ?
N008 C00Z 1.332(3) . ?
N008 C010 1.332(3) . ?
O009 N00R 1.414(3) . ?
O009 C00Y 1.367(3) . ?
O0AA N00D 1.211(3) . ?
O1 N00H 1.217(3) . ?
O00C N00V 1.408(3) . ?
O00C C00W 1.368(3) . ?
N00D O00N 1.210(3) . ?
N00D C00P 1.454(3) . ?
N00E C00Q 1.329(3) . ?
N00E C00Y 1.332(3) . ?
O2 N00M 1.211(3) . ?
N00G C00P 1.287(3) . ?
N00H O00I 1.214(3) . ?
N00H C00S 1.454(3) . ?
O3 N00O 1.214(3) . ?
O00K N00O 1.218(3) . ?
N00L C00W 1.317(3) . ?
N00L C00Z 1.309(4) . ?
N00M O00T 1.217(3) . ?
N00M C010 1.463(4) . ?
N00O C00U 1.455(4) . ?
N00R C00S 1.285(3) . ?
C00U N00V 1.286(4) . ?
N00X C010 1.293(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
N00G Na01 N00G 180.0 57_666 9 ?
N00G Na01 N00G 180.00(10) 5 53_666 ?
N00G Na01 N00G 92.35(8) 57_666 53_666 ?
N00G Na01 N00G 92.35(8) 49_666 53_666 ?
N00G Na01 N00G 92.34(8) 9 . ?
N00G Na01 N00G 92.35(8) 5 . ?
N00G Na01 N00G 87.65(8) 57_666 5 ?
N00G Na01 N00G 92.35(8) 57_666 49_666 ?
N00G Na01 N00G 92.35(8) 9 5 ?
N00G Na01 N00G 87.66(8) 57_666 . ?
N00G Na01 N00G 87.65(8) 49_666 5 ?
N00G Na01 N00G 87.65(8) 9 49_666 ?
N00G Na01 N00G 180.0 49_666 . ?
N00G Na01 N00G 87.65(8) 9 53_666 ?
N00G Na01 N00G 87.65(8) 53_666 . ?
N004 Na02 N005 132.82(8) . . ?
N004 Na02 N006 70.80(7) . . ?
N004 Na02 N008 135.38(8) . . ?
N004 Na02 O0AA 61.66(7) . . ?
N004 Na02 O1 130.28(7) . . ?
N004 Na02 O2 86.47(7) . . ?
N004 Na02 O3 83.71(7) . . ?
N005 Na02 N006 124.57(8) . . ?
N005 Na02 N008 71.18(7) . . ?
N005 Na02 O0AA 86.59(7) . . ?
N005 Na02 O1 76.63(7) . . ?
N005 Na02 O2 131.39(8) . . ?
N005 Na02 O3 59.68(7) . . ?
N006 Na02 N008 132.69(8) . . ?
N006 Na02 O0AA 132.05(7) . . ?
N006 Na02 O1 59.94(7) . . ?
N006 Na02 O2 91.15(7) . . ?
N006 Na02 O3 80.77(7) . . ?
N008 Na02 O0AA 88.79(7) . . ?
N008 Na02 O1 87.13(7) . . ?
N008 Na02 O2 60.22(7) . . ?
N008 Na02 O3 130.85(8) . . ?
O0AA Na02 O1 163.17(8) . . ?
O0AA Na02 O2 91.89(7) . . ?
O0AA Na02 O3 87.98(7) . . ?
O1 Na02 O3 82.40(7) . . ?
O2 Na02 O1 100.19(8) . . ?
O2 Na02 O3 168.91(8) . . ?
C00Q O N00G 106.89(19) . . ?
C00P N004 Na02 124.62(16) . . ?
C00Q N004 Na02 133.60(16) . . ?
C00Q N004 C00P 101.4(2) . . ?
C00U N005 Na02 126.90(17) . . ?
C00W N005 Na02 131.46(17) . . ?
C00W N005 C00U 101.2(2) . . ?
C00S N006 Na02 126.41(17) . . ?
C00Y N006 Na02 131.73(16) . . ?
C00Y N006 C00S 101.7(2) . . ?
C00Z O007 N00X 107.6(2) . . ?
C00Z N008 Na02 131.90(17) . . ?
C010 N008 Na02 126.26(19) . . ?
C010 N008 C00Z 101.7(2) . . ?
C00Y O009 N00R 107.66(19) . . ?
N00D O0AA Na02 117.51(17) . . ?
N00H O1 Na02 116.03(16) . . ?
C00W O00C N00V 107.0(2) . . ?
O0AA N00D C00P 116.9(2) . . ?
O00N N00D O0AA 125.2(3) . . ?
O00N N00D C00P 117.9(2) . . ?
C00Q N00E C00Y 116.6(2) . . ?
N00M O2 Na02 116.29(19) . . ?
O N00G Na01 113.98(14) . . ?
C00P N00G Na01 140.03(18) . . ?
C00P N00G O 101.01(19) . . ?
O1 N00H C00S 116.4(2) . . ?
O00I N00H O1 125.6(3) . . ?
O00I N00H C00S 118.0(2) . . ?
N00O O3 Na02 115.23(17) . . ?
C00Z N00L C00W 117.1(2) . . ?
O2 N00M O00T 125.0(3) . . ?
O2 N00M C010 117.0(2) . . ?
O00T N00M C010 117.9(3) . . ?
O3 N00O O00K 126.0(3) . . ?
O3 N00O C00U 116.8(2) . . ?
O00K N00O C00U 117.2(3) . . ?
N004 C00P N00D 119.1(2) . . ?
N00G C00P N004 119.2(2) . . ?
N00G C00P N00D 121.8(2) . . ?
N004 C00Q O 111.6(2) . . ?
N004 C00Q N00E 132.4(2) . . ?
N00E C00Q O 116.0(2) . . ?
C00S N00R O009 100.5(2) . . ?
N006 C00S N00H 120.9(2) . . ?
N00R C00S N006 119.2(2) . . ?
N00R C00S N00H 119.9(2) . . ?
N005 C00U N00O 120.9(2) . . ?
N00V C00U N005 119.4(3) . . ?
N00V C00U N00O 119.7(3) . . ?
C00U N00V O00C 101.1(2) . . ?
N005 C00W O00C 111.2(2) . . ?
N00L C00W N005 134.4(3) . . ?
N00L C00W O00C 114.4(2) . . ?
C010 N00X O007 101.1(2) . . ?
N006 C00Y O009 110.9(2) . . ?
N006 C00Y N00E 133.8(2) . . ?
N00E C00Y O009 115.2(2) . . ?
N008 C00Z O007 110.6(3) . . ?
N00L C00Z O007 115.8(3) . . ?
N00L C00Z N008 133.6(2) . . ?
N008 C010 N00M 120.0(3) . . ?
N00X C010 N008 119.0(3) . . ?
N00X C010 N00M 121.0(3) . . ?

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 -0.249 -0.202 0.014 4969.3 2341.7 '3 H2O'
2 -0.125 -0.125 0.375 328.5 116.3 '1 H2O'
3 0.125 0.125 0.625 328.5 116.4 '1 H2O'
4 -0.125 0.375 0.875 328.5 116.3 '1 H2O'
5 0.125 0.625 0.125 328.5 116.4 '1 H2O'
6 0.375 0.375 0.375 328.5 116.3 '1 H2O'
7 0.375 0.875 0.875 328.5 116.3 '1 H2O'
8 0.625 0.125 0.125 328.5 116.4 '1 H2O'
9 0.625 0.625 0.625 328.5 116.4 '1 H2O'

_olex2_submission_special_instructions 'No special instructions were received'

####################################################################### 
# 
# 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 1565967'
_audit_update_record             
;
2017-10-15 deposited with the CCDC.
2018-01-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C11 H18 N12 O9'
_chemical_formula_weight         462.37

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'

_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                   8.9077(8)
_cell_length_b                   11.0719(10)
_cell_length_c                   11.9040(10)
_cell_angle_alpha                105.744(3)
_cell_angle_beta                 95.441(3)
_cell_angle_gamma                109.541(3)
_cell_volume                     1042.38(16)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    6280
_cell_measurement_theta_min      2.03
_cell_measurement_theta_max      29.42

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.473
_exptl_crystal_F_000             480
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.128
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  CCD
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12831
_diffrn_reflns_av_unetI/netI     0.0215
_diffrn_reflns_av_R_equivalents  0.0173
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.816
_diffrn_reflns_theta_max         28.248
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             5143
_reflns_number_gt                3559
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0867P)²+0.3072P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5143
_refine_ls_number_parameters     289
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0777
_refine_ls_R_factor_gt           0.0549
_refine_ls_wR_factor_ref         0.1793
_refine_ls_wR_factor_gt          0.1594
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_restrained_S_all      1.049
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.7304(2) 0.6721(2) 0.74597(17) 0.0512(4) Uani 1 1 d . . . . .
C2 C 0.5102(2) 0.52250(19) 0.65901(16) 0.0452(4) Uani 1 1 d . . . . .
C3 C 0.3131(2) 0.10463(19) 0.41516(16) 0.0443(4) Uani 1 1 d . . . . .
C4 C 0.3949(2) -0.04321(19) 0.33587(17) 0.0479(4) Uani 1 1 d . . . . .
C5 C 0.9141(2) 0.3215(2) 0.53891(19) 0.0508(4) Uani 1 1 d . . . . .
C6 C 0.2419(6) 0.4867(3) 1.0444(3) 0.1214(14) Uani 1 1 d . . . . .
H6A H 0.3511 0.5033 1.0829 0.146 Uiso 1 1 calc R U . . .
H6B H 0.1998 0.5430 1.0995 0.146 Uiso 1 1 calc R U . . .
C7 C 0.2509(6) 0.5275(3) 0.9401(3) 0.1189(13) Uani 1 1 d . . . . .
H7A H 0.1464 0.5290 0.9108 0.143 Uiso 1 1 calc R U . . .
H7B H 0.3310 0.6190 0.9620 0.143 Uiso 1 1 calc R U . . .
C8 C 0.1906(5) 0.3066(3) 0.8222(3) 0.1026(10) Uani 1 1 d . . . . .
H8A H 0.2293 0.2498 0.7646 0.123 Uiso 1 1 calc R U . . .
H8B H 0.0813 0.2932 0.7866 0.123 Uiso 1 1 calc R U . . .
C9 C 0.1856(6) 0.2655(3) 0.9272(3) 0.1185(13) Uani 1 1 d . . . . .
H9A H 0.1056 0.1741 0.9063 0.142 Uiso 1 1 calc R U . . .
H9B H 0.2908 0.2639 0.9546 0.142 Uiso 1 1 calc R U . . .
C11 C 0.3445(3) 0.9448(3) 1.0186(2) 0.0728(6) Uani 1 1 d . . . . .
H11C H 0.3119 1.0220 1.0387 0.087 Uiso 1 1 calc R U . . .
H11D H 0.2543 0.8660 1.0191 0.087 Uiso 1 1 calc R U . . .
C13 C 0.3829(3) 0.9221(4) 0.8993(3) 0.0946(9) Uani 1 1 d . . . . .
H13A H 0.4049 0.8397 0.8764 0.114 Uiso 1 1 calc R U . . .
H13B H 0.2894 0.9102 0.8424 0.114 Uiso 1 1 calc R U . . .
N1 N 0.9069(2) 0.7448(2) 0.78590(18) 0.0656(5) Uani 1 1 d . . . . .
N2 N 0.6345(2) 0.73593(19) 0.77505(17) 0.0638(5) Uani 1 1 d . . . . .
N3 N 0.66529(18) 0.54195(16) 0.67540(13) 0.0469(4) Uani 1 1 d . . . . .
N4 N 0.37302(18) 0.41531(17) 0.59432(14) 0.0475(4) Uani 1 1 d . . . . .
N5 N 0.40796(17) 0.31369(16) 0.53717(13) 0.0426(3) Uani 1 1 d . . . . .
N6 N 0.27598(17) 0.21056(17) 0.47444(14) 0.0475(4) Uani 1 1 d . . . . .
N7 N 0.45056(17) 0.08575(15) 0.40903(13) 0.0439(3) Uani 1 1 d . . . . .
N8 N 0.2402(2) -0.10719(19) 0.29620(18) 0.0641(5) Uani 1 1 d . . . . .
N9 N 0.5056(2) -0.11333(18) 0.30375(15) 0.0560(4) Uani 1 1 d . . . . .
N10 N 1.0384(2) 0.4274(2) 0.60904(19) 0.0690(5) Uani 1 1 d . . . . .
H10A H 1.0233 0.4978 0.6500 0.083 Uiso 1 1 calc R U . . .
H10B H 1.1349 0.4264 0.6140 0.083 Uiso 1 1 calc R U . . .
N11 N 0.9382(2) 0.2145(2) 0.47514(18) 0.0673(5) Uani 1 1 d . . . . .
H11A H 1.0351 0.2143 0.4796 0.081 Uiso 1 1 calc R U . . .
H11B H 0.8571 0.1449 0.4291 0.081 Uiso 1 1 calc R U . . .
N12 N 0.76611(19) 0.3224(2) 0.53091(18) 0.0624(5) Uani 1 1 d . . . . .
H12A H 0.7505 0.3926 0.5718 0.075 Uiso 1 1 calc R U . . .
H12B H 0.6850 0.2528 0.4849 0.075 Uiso 1 1 calc R U . . .
O1 O 0.9544(3) 0.86376(19) 0.8444(2) 0.1005(7) Uani 1 1 d . . . . .
O2 O 0.9919(2) 0.6808(2) 0.75584(18) 0.0832(5) Uani 1 1 d . . . . .
O3 O 0.48248(18) 0.63384(15) 0.71605(14) 0.0604(4) Uani 1 1 d . . . . .
O4 O 0.18242(16) -0.00568(15) 0.34955(14) 0.0619(4) Uani 1 1 d . . . . .
O5 O 0.65043(19) -0.04650(17) 0.33758(15) 0.0673(4) Uani 1 1 d . . . . .
O6 O 0.4450(2) -0.23306(17) 0.24810(18) 0.0830(5) Uani 1 1 d . . . . .
O7 O 0.2925(3) 0.4433(2) 0.84777(19) 0.0990(7) Uani 1 1 d . . . . .
O8 O 0.1459(3) 0.3527(2) 1.02297(17) 0.1017(7) Uani 1 1 d . . . . .
O10 O 0.4810(2) 0.9687(2) 1.10472(17) 0.0922(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 N2 1.295(3) . ?
C1 N3 1.345(2) . ?
C1 N1 1.466(3) . ?
C2 N3 1.311(2) . ?
C2 O3 1.350(2) . ?
C2 N4 1.360(3) . ?
C3 N7 1.314(2) . ?
C3 O4 1.348(2) . ?
C3 N6 1.356(2) . ?
C4 N8 1.290(3) . ?
C4 N7 1.346(2) . ?
C4 N9 1.464(2) . ?
C5 N10 1.312(3) . ?
C5 N12 1.317(2) . ?
C5 N11 1.319(3) . ?
C6 O8 1.380(4) . ?
C6 C7 1.432(5) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 O7 1.402(4) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 O7 1.409(4) . ?
C8 C9 1.441(5) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 O8 1.437(4) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C11 O10 1.414(3) . ?
C11 C13 1.467(4) . ?
C11 H11C 0.9700 . ?
C11 H11D 0.9700 . ?
C13 O10 1.413(3) 2_677 ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
N1 O1 1.214(3) . ?
N1 O2 1.215(3) . ?
N2 O3 1.404(2) . ?
N4 N5 1.298(2) . ?
N5 N6 1.310(2) . ?
N8 O4 1.412(2) . ?
N9 O6 1.210(2) . ?
N9 O5 1.215(2) . ?
N10 H10A 0.8600 . ?
N10 H10B 0.8600 . ?
N11 H11A 0.8600 . ?
N11 H11B 0.8600 . ?
N12 H12A 0.8600 . ?
N12 H12B 0.8600 . ?
O10 C13 1.413(3) 2_677 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 C1 N3 118.85(18) . . ?
N2 C1 N1 119.37(19) . . ?
N3 C1 N1 121.72(18) . . ?
N3 C2 O3 112.74(17) . . ?
N3 C2 N4 133.43(17) . . ?
O3 C2 N4 113.80(15) . . ?
N7 C3 O4 112.59(16) . . ?
N7 C3 N6 133.48(16) . . ?
O4 C3 N6 113.93(15) . . ?
N8 C4 N7 119.08(17) . . ?
N8 C4 N9 119.51(18) . . ?
N7 C4 N9 121.38(17) . . ?
N10 C5 N12 120.3(2) . . ?
N10 C5 N11 119.73(17) . . ?
N12 C5 N11 120.0(2) . . ?
O8 C6 C7 114.6(3) . . ?
O8 C6 H6A 108.6 . . ?
C7 C6 H6A 108.6 . . ?
O8 C6 H6B 108.6 . . ?
C7 C6 H6B 108.6 . . ?
H6A C6 H6B 107.6 . . ?
O7 C7 C6 113.9(3) . . ?
O7 C7 H7A 108.8 . . ?
C6 C7 H7A 108.8 . . ?
O7 C7 H7B 108.8 . . ?
C6 C7 H7B 108.8 . . ?
H7A C7 H7B 107.7 . . ?
O7 C8 C9 112.3(3) . . ?
O7 C8 H8A 109.1 . . ?
C9 C8 H8A 109.1 . . ?
O7 C8 H8B 109.1 . . ?
C9 C8 H8B 109.1 . . ?
H8A C8 H8B 107.9 . . ?
O8 C9 C8 113.4(3) . . ?
O8 C9 H9A 108.9 . . ?
C8 C9 H9A 108.9 . . ?
O8 C9 H9B 108.9 . . ?
C8 C9 H9B 108.9 . . ?
H9A C9 H9B 107.7 . . ?
O10 C11 C13 110.7(2) . . ?
O10 C11 H11C 109.5 . . ?
C13 C11 H11C 109.5 . . ?
O10 C11 H11D 109.5 . . ?
C13 C11 H11D 109.5 . . ?
H11C C11 H11D 108.1 . . ?
O10 C13 C11 111.8(2) 2_677 . ?
O10 C13 H13A 109.3 2_677 . ?
C11 C13 H13A 109.3 . . ?
O10 C13 H13B 109.3 2_677 . ?
C11 C13 H13B 109.3 . . ?
H13A C13 H13B 107.9 . . ?
O1 N1 O2 126.1(2) . . ?
O1 N1 C1 116.9(2) . . ?
O2 N1 C1 116.96(19) . . ?
C1 N2 O3 100.80(16) . . ?
C2 N3 C1 100.53(16) . . ?
N5 N4 C2 110.98(14) . . ?
N4 N5 N6 111.05(13) . . ?
N5 N6 C3 110.80(14) . . ?
C3 N7 C4 100.57(15) . . ?
C4 N8 O4 100.60(15) . . ?
O6 N9 O5 125.72(19) . . ?
O6 N9 C4 117.33(19) . . ?
O5 N9 C4 116.93(17) . . ?
C5 N10 H10A 120.0 . . ?
C5 N10 H10B 120.0 . . ?
H10A N10 H10B 120.0 . . ?
C5 N11 H11A 120.0 . . ?
C5 N11 H11B 120.0 . . ?
H11A N11 H11B 120.0 . . ?
C5 N12 H12A 120.0 . . ?
C5 N12 H12B 120.0 . . ?
H12A N12 H12B 120.0 . . ?
C2 O3 N2 107.09(14) . . ?
C3 O4 N8 107.16(14) . . ?
C7 O7 C8 110.8(3) . . ?
C6 O8 C9 111.0(3) . . ?
C13 O10 C11 110.6(2) 2_677 . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O8 C6 C7 O7 -51.4(6) . . . . ?
O7 C8 C9 O8 52.7(5) . . . . ?
O10 C11 C13 O10 -56.3(4) . . . 2_677 ?
N2 C1 N1 O1 -0.7(3) . . . . ?
N3 C1 N1 O1 176.4(2) . . . . ?
N2 C1 N1 O2 -179.6(2) . . . . ?
N3 C1 N1 O2 -2.5(3) . . . . ?
N3 C1 N2 O3 0.4(2) . . . . ?
N1 C1 N2 O3 177.51(17) . . . . ?
O3 C2 N3 C1 0.0(2) . . . . ?
N4 C2 N3 C1 177.9(2) . . . . ?
N2 C1 N3 C2 -0.2(2) . . . . ?
N1 C1 N3 C2 -177.32(18) . . . . ?
N3 C2 N4 N5 -0.9(3) . . . . ?
O3 C2 N4 N5 176.97(15) . . . . ?
C2 N4 N5 N6 -179.74(15) . . . . ?
N4 N5 N6 C3 -179.87(15) . . . . ?
N7 C3 N6 N5 0.4(3) . . . . ?
O4 C3 N6 N5 179.39(15) . . . . ?
O4 C3 N7 C4 -0.2(2) . . . . ?
N6 C3 N7 C4 178.8(2) . . . . ?
N8 C4 N7 C3 -0.4(2) . . . . ?
N9 C4 N7 C3 -178.34(17) . . . . ?
N7 C4 N8 O4 0.7(2) . . . . ?
N9 C4 N8 O4 178.73(16) . . . . ?
N8 C4 N9 O6 -5.6(3) . . . . ?
N7 C4 N9 O6 172.32(19) . . . . ?
N8 C4 N9 O5 175.83(19) . . . . ?
N7 C4 N9 O5 -6.2(3) . . . . ?
N3 C2 O3 N2 0.2(2) . . . . ?
N4 C2 O3 N2 -178.12(16) . . . . ?
C1 N2 O3 C2 -0.3(2) . . . . ?
N7 C3 O4 N8 0.6(2) . . . . ?
N6 C3 O4 N8 -178.60(16) . . . . ?
C4 N8 O4 C3 -0.8(2) . . . . ?
C6 C7 O7 C8 51.7(5) . . . . ?
C9 C8 O7 C7 -52.5(4) . . . . ?
C7 C6 O8 C9 48.8(5) . . . . ?
C8 C9 O8 C6 -49.9(5) . . . . ?
C13 C11 O10 C13 55.6(4) . . . 2_677 ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N12 H12B N7 0.86 2.18 3.018(2) 164.9 .
N12 H12A N3 0.86 2.18 3.026(2) 168.8 .
N11 H11B O5 0.86 2.20 3.047(3) 170.0 .
N11 H11A N6 0.86 2.17 3.024(2) 175.0 1_655
N10 H10B N4 0.86 2.20 3.048(2) 170.5 1_655
N10 H10A O2 0.86 2.20 3.058(3) 178.5 .

_refine_diff_density_max         0.398
_refine_diff_density_min         -0.293
_refine_diff_density_rms         0.041

_shelxl_version_number           2014-3

