# 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 2017

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

data_mo_2016160_0m
_database_code_depnum_ccdc_archive 'CCDC 1506811'
_audit_update_record             
;
2017-07-09 deposited with the CCDC.
2017-07-12 downloaded from the CCDC.
;
_audit_creation_date             2017-07-05
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5361)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C3 H N9 O10, 2(H2 O)'
_chemical_formula_sum            'C3 H5 N9 O12'
_chemical_formula_weight         359.16
_chemical_absolute_configuration ?
_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'
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      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   7.4840(4)
_cell_length_b                   7.8907(4)
_cell_length_c                   10.2465(5)
_cell_angle_alpha                90
_cell_angle_beta                 93.122(3)
_cell_angle_gamma                90
_cell_volume                     604.20(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4367
_cell_measurement_temperature    296
_cell_measurement_theta_max      27.461
_cell_measurement_theta_min      2.725
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.200
_exptl_absorpt_correction_T_max  0.957
_exptl_absorpt_correction_T_min  0.946
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2008/1 (Bruker,2008) was used for absorption correction. wR2(int) was 0.0431 before and 0.0326 after correction. The Ratio of minimum to maximum transmission is 0.9359. The λ/2 correction factor is 0.0015.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear whiteish colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.974
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             364
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.22
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0490
_diffrn_reflns_av_unetI/netI     0.0309
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            5452
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.465
_diffrn_reflns_theta_min         1.990
_diffrn_ambient_temperature      296
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.868
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                2549
_reflns_number_total             2641
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_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    'SIR2004 (Burla et al., 2007)'
_refine_diff_density_max         0.355
_refine_diff_density_min         -0.464
_refine_diff_density_rms         0.085
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   -2(2)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.261
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     224
_refine_ls_number_reflns         2641
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0379
_refine_ls_R_factor_gt           0.0314
_refine_ls_restrained_S_all      1.266
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0732P)²+0.2583P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0867
_refine_ls_wR_factor_ref         0.1263
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 3(2)
 -2(2)
2. Fixed Uiso
 At 1.2 times of:
  All N(H) groups
 At 1.5 times of:
  All O(H,H) groups
3. Restrained distances
 H2WA-H2WB
 1.46 with sigma of 0.02
 H1WB-H1WA
 1.46 with sigma of 0.02
4.a Free rotating group:
 O2W(H2WA,H2WB), O1W(H1WA,H1WB)
4.b Aromatic/amide H refined with riding coordinates:
 N4(H4)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
_atom_sites_special_details      
;
The structure was solved using Direct Methods (ShelXS). RE = 0.1, Nqual =  -1, Ralpha = 0.048
;
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 0.8689(4) 3.1580(4) 2.9608(3) 0.0220(6) Uani 1 1 d . . . . .
O2W O 0.5742(4) 3.4277(3) 2.9129(3) 0.0194(5) Uani 1 1 d . . . . .
H2WA H 0.5413 3.3252 2.9200 0.029 Uiso 1 1 d DG . . . .
H2WB H 0.6830 3.4307 2.8932 0.029 Uiso 1 1 d DG . . . .
O2 O 0.7321(4) 3.9453(3) 2.7412(3) 0.0203(6) Uani 1 1 d . . . . .
O1 O 0.7361(4) 3.7504(4) 2.8916(3) 0.0207(6) Uani 1 1 d . . . . .
O3 O 1.1035(4) 3.0546(3) 2.8703(3) 0.0201(6) Uani 1 1 d . . . . .
O1W O 0.4868(4) 3.1087(3) 2.8789(3) 0.0198(6) Uani 1 1 d . . . . .
H1WA H 0.5637 3.0443 2.8462 0.030 Uiso 1 1 d DG . . . .
H1WB H 0.3888 3.1030 2.8331 0.030 Uiso 1 1 d DG . . . .
O6 O 1.3084(4) 3.9004(4) 2.6386(3) 0.0245(6) Uani 1 1 d . . . . .
O8 O 1.2315(5) 3.7271(4) 2.4212(3) 0.0274(7) Uani 1 1 d . . . . .
O10 O 1.5427(4) 3.5615(4) 2.6353(3) 0.0263(6) Uani 1 1 d . . . . .
O9 O 1.3658(4) 3.3737(4) 2.5385(3) 0.0269(6) Uani 1 1 d . . . . .
O5 O 1.3328(4) 3.7486(4) 2.8163(3) 0.0241(6) Uani 1 1 d . . . . .
O7 O 0.9943(4) 3.5896(5) 2.4699(3) 0.0296(7) Uani 1 1 d . . . . .
N6 N 0.9961(4) 3.1672(4) 2.8901(3) 0.0152(6) Uani 1 1 d . . . . .
N1 N 0.8958(4) 3.4551(4) 2.8317(3) 0.0140(6) Uani 1 1 d . . . . .
N7 N 1.2966(4) 3.7711(4) 2.7000(3) 0.0158(6) Uani 1 1 d . . . . .
N5 N 0.7897(4) 3.8083(4) 2.7889(3) 0.0149(6) Uani 1 1 d . . . . .
N3 N 1.1204(4) 3.5144(4) 2.7094(3) 0.0153(6) Uani 1 1 d . . . . .
N8 N 1.1419(4) 3.6463(4) 2.4923(3) 0.0180(6) Uani 1 1 d . . . . .
N2 N 1.1572(4) 3.3537(4) 2.7544(3) 0.0147(6) Uani 1 1 d . . . . .
N4 N 0.9170(4) 3.7339(4) 2.7218(3) 0.0167(6) Uani 1 1 d . . . . .
H4 H 0.9658 3.7844 2.6585 0.020 Uiso 1 1 calc R . . . .
N9 N 1.3987(4) 3.5018(4) 2.5988(3) 0.0169(6) Uani 1 1 d . . . . .
C2 C 0.9640(5) 3.5768(4) 2.7588(3) 0.0140(6) Uani 1 1 d . . . . .
C1 C 1.0190(5) 3.3288(4) 2.8237(3) 0.0127(6) Uani 1 1 d . . . . .
C3 C 1.2323(5) 3.6060(4) 2.6291(3) 0.0139(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
O4 N6 1.230(4) . ?
O2W H2WA 0.8499 . ?
O2W H2WB 0.8501 . ?
O2 N5 1.254(4) . ?
O1 N5 1.234(4) . ?
O3 N6 1.222(4) . ?
O1W H1WA 0.8502 . ?
O1W H1WB 0.8502 . ?
O6 N7 1.204(4) . ?
O8 N8 1.201(4) . ?
O10 N9 1.217(5) . ?
O9 N9 1.203(4) . ?
O5 N7 1.220(4) . ?
O7 N8 1.203(5) . ?
N6 C1 1.460(4) . ?
N1 C2 1.335(5) . ?
N1 C1 1.364(4) . ?
N7 C3 1.555(4) . ?
N5 N4 1.340(5) . ?
N3 N2 1.373(4) . ?
N3 C2 1.391(4) . ?
N3 C3 1.406(5) . ?
N8 C3 1.556(4) . ?
N2 C1 1.301(5) . ?
N4 H4 0.8600 . ?
N4 C2 1.337(5) . ?
N9 C3 1.538(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
H2WA O2W H2WB 109.5 . . ?
H1WA O1W H1WB 109.5 . . ?
O4 N6 C1 116.1(3) . . ?
O3 N6 O4 126.3(3) . . ?
O3 N6 C1 117.6(3) . . ?
C2 N1 C1 102.2(3) . . ?
O6 N7 O5 128.0(3) . . ?
O6 N7 C3 119.7(3) . . ?
O5 N7 C3 112.3(3) . . ?
O2 N5 N4 114.6(3) . . ?
O1 N5 O2 122.1(3) . . ?
O1 N5 N4 123.3(3) . . ?
N2 N3 C2 111.3(3) . . ?
N2 N3 C3 123.8(3) . . ?
C2 N3 C3 124.8(3) . . ?
O8 N8 O7 128.3(3) . . ?
O8 N8 C3 115.2(3) . . ?
O7 N8 C3 116.5(3) . . ?
C1 N2 N3 99.9(3) . . ?
N5 N4 H4 121.8 . . ?
C2 N4 N5 116.3(3) . . ?
C2 N4 H4 121.8 . . ?
O10 N9 C3 116.4(3) . . ?
O9 N9 O10 129.5(3) . . ?
O9 N9 C3 114.1(3) . . ?
N1 C2 N3 107.7(3) . . ?
N1 C2 N4 136.3(3) . . ?
N4 C2 N3 116.0(3) . . ?
N1 C1 N6 120.9(3) . . ?
N2 C1 N6 120.2(3) . . ?
N2 C1 N1 118.9(3) . . ?
N7 C3 N8 111.0(3) . . ?
N3 C3 N7 109.7(3) . . ?
N3 C3 N8 112.8(3) . . ?
N3 C3 N9 111.0(3) . . ?
N9 C3 N7 108.0(3) . . ?
N9 C3 N8 104.1(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O4 N6 C1 N1 -5.6(5) . . . . ?
O4 N6 C1 N2 175.1(3) . . . . ?
O2 N5 N4 C2 -170.9(3) . . . . ?
O1 N5 N4 C2 11.1(5) . . . . ?
O3 N6 C1 N1 174.2(3) . . . . ?
O3 N6 C1 N2 -5.1(5) . . . . ?
O6 N7 C3 N3 -141.2(3) . . . . ?
O6 N7 C3 N8 -15.8(5) . . . . ?
O6 N7 C3 N9 97.7(4) . . . . ?
O8 N8 C3 N7 55.2(4) . . . . ?
O8 N8 C3 N3 178.7(3) . . . . ?
O8 N8 C3 N9 -60.8(4) . . . . ?
O10 N9 C3 N7 1.2(4) . . . . ?
O10 N9 C3 N3 -119.1(3) . . . . ?
O10 N9 C3 N8 119.2(3) . . . . ?
O9 N9 C3 N7 -176.9(3) . . . . ?
O9 N9 C3 N3 62.8(4) . . . . ?
O9 N9 C3 N8 -58.9(4) . . . . ?
O5 N7 C3 N3 40.1(4) . . . . ?
O5 N7 C3 N8 165.4(3) . . . . ?
O5 N7 C3 N9 -81.0(3) . . . . ?
O7 N8 C3 N7 -126.7(3) . . . . ?
O7 N8 C3 N3 -3.1(5) . . . . ?
O7 N8 C3 N9 117.3(3) . . . . ?
N5 N4 C2 N1 15.6(6) . . . . ?
N5 N4 C2 N3 -166.5(3) . . . . ?
N3 N2 C1 N6 178.3(3) . . . . ?
N3 N2 C1 N1 -1.1(4) . . . . ?
N2 N3 C2 N1 -2.2(4) . . . . ?
N2 N3 C2 N4 179.3(3) . . . . ?
N2 N3 C3 N7 -118.9(3) . . . . ?
N2 N3 C3 N8 116.8(3) . . . . ?
N2 N3 C3 N9 0.4(4) . . . . ?
C2 N1 C1 N6 -179.6(3) . . . . ?
C2 N1 C1 N2 -0.2(4) . . . . ?
C2 N3 N2 C1 1.9(3) . . . . ?
C2 N3 C3 N7 57.6(4) . . . . ?
C2 N3 C3 N8 -66.6(4) . . . . ?
C2 N3 C3 N9 176.9(3) . . . . ?
C1 N1 C2 N3 1.4(4) . . . . ?
C1 N1 C2 N4 179.5(4) . . . . ?
C3 N3 N2 C1 178.9(3) . . . . ?
C3 N3 C2 N1 -179.1(3) . . . . ?
C3 N3 C2 N4 2.4(5) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 3(2)
2 -2(2)

####################################################################### 
# 
# 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_a
_database_code_depnum_ccdc_archive 'CCDC 1502833'
_audit_update_record             
;
2016-09-06 deposited with the CCDC.
2017-07-12 downloaded from the CCDC.
;
_audit_creation_date             2016-06-03
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C3 N9 O10, C2 H5 N4'
_chemical_formula_sum            'C5 H5 N13 O10'
_chemical_formula_weight         407.22
_chemical_absolute_configuration ?
_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'
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      orthorhombic
_space_group_IT_number           29
_space_group_name_H-M_alt        'P c a 21'
_space_group_name_Hall           'P 2c -2ac'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y, z'
'-x+1/2, y, z+1/2'

_cell_length_a                   23.003(2)
_cell_length_b                   6.7490(7)
_cell_length_c                   19.422(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3015.1(6)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    3572
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      20.377
_cell_measurement_theta_min      2.745
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.170
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6181
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0748 before and 0.0569 after correction.
The Ratio of minimum to maximum transmission is 0.8290.
The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear whiteish colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.794
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1648
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0483
_diffrn_reflns_av_unetI/netI     0.0594
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            22518
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.370
_diffrn_reflns_theta_min         1.771
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.939
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                3165
_reflns_number_total             5696
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_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         0.468
_refine_diff_density_min         -0.244
_refine_diff_density_rms         0.052
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     512
_refine_ls_number_reflns         5696
_refine_ls_number_restraints     166
_refine_ls_R_factor_all          0.1222
_refine_ls_R_factor_gt           0.0602
_refine_ls_restrained_S_all      0.999
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0972P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1454
_refine_ls_wR_factor_ref         0.1774
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 1(3) 0(3)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups, All N(H,H) groups
3. Restrained distances
 O2-N4
 2.9 with sigma of 0.02
 O12-N17
 2.9 with sigma of 0.02
 N17-H17
 0.88 with sigma of 0.02
4. Restrained planarity
 C6, C7, N15, N16, N17
 with sigma of 0.1
5. Rigid bond restraints
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
6. Uiso/Uaniso restraints and constraints
Uanis(O16) \\sim Ueq, Uanis(O15) \\sim Ueq, Uanis(N25) \\sim Ueq: with sigma of
0.1 and sigma for terminal atoms of 0.2
Uanis(C7) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
7.a Rotating group:
 N14(H14A,H14B), N1(H1A,H1B)
7.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C1(H1), C2(H2), N4(H4)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_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
C3 C -0.3346(3) -0.6836(9) -0.3949(4) 0.0459(15) Uani 1 1 d . U . . .
C4 C -0.4066(3) -0.8443(9) -0.3624(4) 0.0476(15) Uani 1 1 d . U . . .
C5 C -0.3883(3) -0.5039(10) -0.4876(4) 0.0484(16) Uani 1 1 d . U . . .
N5 N -0.2387(3) -0.6228(9) -0.3790(4) 0.0610(17) Uani 1 1 d . U . . .
N6 N -0.2868(2) -0.5852(8) -0.4135(4) 0.0590(17) Uani 1 1 d . U . . .
N7 N -0.3501(2) -0.8194(8) -0.3488(3) 0.0503(14) Uani 1 1 d . U . . .
N8 N -0.4416(3) -0.9829(9) -0.3220(4) 0.0600(16) Uani 1 1 d . U . . .
N9 N -0.4311(2) -0.7468(8) -0.4114(3) 0.0507(14) Uani 1 1 d . U . . .
N10 N -0.3840(2) -0.6391(8) -0.4333(3) 0.0487(14) Uani 1 1 d . U . . .
N11 N -0.3561(3) -0.5775(13) -0.5524(4) 0.0733(19) Uani 1 1 d . U . . .
N12 N -0.3661(3) -0.2969(11) -0.4658(5) 0.076(2) Uani 1 1 d . U . . .
N13 N -0.4522(3) -0.4781(11) -0.5088(4) 0.0659(17) Uani 1 1 d . U . . .
O1 O -0.2352(2) -0.7431(9) -0.3315(3) 0.0816(17) Uani 1 1 d . U . . .
O2 O -0.1950(2) -0.5238(9) -0.3963(4) 0.0855(19) Uani 1 1 d D U . . .
O3 O -0.4182(3) -1.0709(9) -0.2761(3) 0.0765(16) Uani 1 1 d . U . . .
O4 O -0.4927(3) -1.0016(11) -0.3368(4) 0.104(2) Uani 1 1 d . U . . .
O5 O -0.3343(3) -0.7382(9) -0.5482(3) 0.0850(18) Uani 1 1 d . U . . .
O6 O -0.3593(4) -0.4750(14) -0.6019(5) 0.140(4) Uani 1 1 d . U . . .
O7 O -0.3509(4) -0.1904(12) -0.5111(5) 0.136(3) Uani 1 1 d . U . . .
O8 O -0.3695(4) -0.2640(10) -0.4057(5) 0.115(3) Uani 1 1 d . U . . .
O9 O -0.4697(3) -0.5777(15) -0.5540(5) 0.119(3) Uani 1 1 d . U . . .
O10 O -0.4791(3) -0.3617(10) -0.4739(4) 0.106(2) Uani 1 1 d . U . . .
C8 C -0.5852(3) -0.1245(10) -0.6065(4) 0.0485(16) Uani 1 1 d . U . . .
C9 C -0.6574(3) -0.2824(9) -0.6406(4) 0.0477(16) Uani 1 1 d . U . . .
C10 C -0.6378(3) 0.0677(10) -0.5186(4) 0.0528(17) Uani 1 1 d . U . . .
N18 N -0.4871(3) -0.0855(10) -0.6183(4) 0.0612(16) Uani 1 1 d . U . . .
N19 N -0.5358(3) -0.0328(9) -0.5871(3) 0.0619(17) Uani 1 1 d . U . . .
N20 N -0.5998(2) -0.2620(7) -0.6516(3) 0.0514(14) Uani 1 1 d . U . . .
N21 N -0.6922(3) -0.4210(9) -0.6815(4) 0.0606(16) Uani 1 1 d . U . . .
N22 N -0.6820(2) -0.1748(8) -0.5933(3) 0.0504(13) Uani 1 1 d . U . . .
N23 N -0.6343(2) -0.0654(8) -0.5712(3) 0.0508(14) Uani 1 1 d . U . . .
N24 N -0.6127(3) -0.0156(14) -0.4510(4) 0.089(2) Uani 1 1 d . U . . .
N25 N -0.6092(4) 0.2665(12) -0.5372(7) 0.097(3) Uani 1 1 d . U . . .
N26 N -0.7030(3) 0.1151(11) -0.5034(4) 0.0672(17) Uani 1 1 d . U . . .
O11 O -0.4854(2) -0.2112(11) -0.6636(4) 0.103(2) Uani 1 1 d . U . . .
O12 O -0.4431(2) -0.0004(10) -0.6004(4) 0.097(2) Uani 1 1 d D U . . .
O13 O -0.6661(3) -0.5163(8) -0.7249(3) 0.0792(17) Uani 1 1 d . U . . .
O14 O -0.7428(3) -0.4334(10) -0.6689(4) 0.099(2) Uani 1 1 d . U . . .
O15 O -0.6102(4) 0.3105(12) -0.5943(7) 0.147(4) Uani 1 1 d . U . . .
O16 O -0.5875(5) 0.3508(17) -0.4884(7) 0.216(7) Uani 1 1 d . U . . .
O17 O -0.5932(3) -0.1787(11) -0.4530(4) 0.098(2) Uani 1 1 d . U . . .
O18 O -0.6202(4) 0.0780(17) -0.3989(5) 0.153(4) Uani 1 1 d . U . . .
O19 O -0.7251(3) 0.0232(12) -0.4581(4) 0.106(2) Uani 1 1 d . U . . .
O20 O -0.7243(3) 0.2396(11) -0.5398(4) 0.100(2) Uani 1 1 d . U . . .
C6 C -0.3024(4) -0.1963(12) -0.7717(5) 0.077(2) Uani 1 1 d . U . . .
H6 H -0.2909 -0.2551 -0.8128 0.092 Uiso 1 1 calc R . . . .
C7 C -0.3000(3) -0.0334(10) -0.6777(4) 0.0554(19) Uani 1 1 d . U . . .
H7 H -0.2879 0.0430 -0.6405 0.066 Uiso 1 1 calc R . . . .
N14 N -0.2091(3) -0.0425(10) -0.7373(4) 0.0684(18) Uani 1 1 d . U . . .
H14A H -0.1885 -0.1492 -0.7370 0.082 Uiso 1 1 d GR . . . .
H14B H -0.2037 0.0193 -0.7755 0.082 Uiso 1 1 d GR . . . .
N15 N -0.2678(3) -0.0894(9) -0.7306(3) 0.0557(15) Uani 1 1 d . U . . .
N16 N -0.3552(3) -0.2061(12) -0.7455(5) 0.086(2) Uani 1 1 d . U . . .
N17 N -0.3507(3) -0.1037(11) -0.6873(4) 0.0707(18) Uani 1 1 d D U . . .
H17 H -0.383(2) -0.086(14) -0.663(4) 0.09(3) Uiso 1 1 d D . . . .
C1 C -0.0486(4) -0.6618(13) -0.2266(6) 0.086(3) Uani 1 1 d . U . . .
H1 H -0.0350 -0.7046 -0.1841 0.103 Uiso 1 1 calc R . . . .
C2 C -0.0501(4) -0.5153(12) -0.3227(5) 0.068(2) Uani 1 1 d . U . . .
H2 H -0.0398 -0.4421 -0.3615 0.082 Uiso 1 1 calc R . . . .
N1 N 0.0386(3) -0.4850(10) -0.2642(5) 0.082(2) Uani 1 1 d . U . . .
H1A H 0.0617 -0.5847 -0.2690 0.099 Uiso 1 1 d GR . . . .
H1B H 0.0460 -0.3985 -0.2957 0.099 Uiso 1 1 d GR . . . .
N2 N -0.0181(3) -0.5519(9) -0.2704(4) 0.0643(17) Uani 1 1 d . U . . .
N3 N -0.1007(4) -0.7022(13) -0.2512(6) 0.104(3) Uani 1 1 d . U . . .
N4 N -0.1005(3) -0.6018(12) -0.3109(5) 0.087(2) Uani 1 1 d D U . . .
H4 H -0.1298 -0.5946 -0.3382 0.104 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C3 N6 1.333(8) . ?
C3 N7 1.330(8) . ?
C3 N10 1.392(8) . ?
C4 N7 1.337(8) . ?
C4 N8 1.462(9) . ?
C4 N9 1.288(8) . ?
C5 N10 1.398(9) . ?
C5 N11 1.542(11) . ?
C5 N12 1.547(10) . ?
C5 N13 1.535(10) . ?
N5 N6 1.319(9) . ?
N5 O1 1.231(8) . ?
N5 O2 1.253(8) . ?
N8 O3 1.199(8) . ?
N8 O4 1.216(9) . ?
N9 N10 1.374(7) . ?
N11 O5 1.198(8) . ?
N11 O6 1.186(10) . ?
N12 O7 1.189(11) . ?
N12 O8 1.191(11) . ?
N13 O9 1.178(10) . ?
N13 O10 1.207(9) . ?
C8 N19 1.346(9) . ?
C8 N20 1.321(9) . ?
C8 N23 1.380(8) . ?
C9 N20 1.348(9) . ?
C9 N21 1.466(9) . ?
C9 N22 1.300(9) . ?
C10 N23 1.363(9) . ?
C10 N24 1.542(11) . ?
C10 N25 1.537(12) . ?
C10 N26 1.561(10) . ?
N18 N19 1.322(8) . ?
N18 O11 1.224(8) . ?
N18 O12 1.215(8) . ?
N21 O13 1.218(9) . ?
N21 O14 1.192(9) . ?
N22 N23 1.390(8) . ?
N24 O17 1.189(10) . ?
N24 O18 1.205(10) . ?
N25 O15 1.148(14) . ?
N25 O16 1.213(15) . ?
N26 O19 1.191(9) . ?
N26 O20 1.203(9) . ?
C6 H6 0.9300 . ?
C6 N15 1.338(10) . ?
C6 N16 1.318(12) . ?
C7 H7 0.9300 . ?
C7 N15 1.321(10) . ?
C7 N17 1.271(10) . ?
N14 H14A 0.8609 . ?
N14 H14B 0.8613 . ?
N14 N15 1.394(8) . ?
N16 N17 1.330(10) . ?
N17 H17 0.89(3) . ?
C1 H1 0.9300 . ?
C1 N2 1.330(11) . ?
C1 N3 1.318(13) . ?
C2 H2 0.9300 . ?
C2 N2 1.278(10) . ?
C2 N4 1.318(11) . ?
N1 H1A 0.8620 . ?
N1 H1B 0.8625 . ?
N1 N2 1.385(9) . ?
N3 N4 1.343(12) . ?
N4 H4 0.8600 . ?

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 C3 N10 114.8(6) . . ?
N7 C3 N6 138.3(6) . . ?
N7 C3 N10 106.9(5) . . ?
N7 C4 N8 120.7(6) . . ?
N9 C4 N7 120.5(6) . . ?
N9 C4 N8 118.8(6) . . ?
N10 C5 N11 111.7(5) . . ?
N10 C5 N12 111.1(7) . . ?
N10 C5 N13 110.2(5) . . ?
N11 C5 N12 110.8(6) . . ?
N13 C5 N11 106.1(6) . . ?
N13 C5 N12 106.7(5) . . ?
O1 N5 N6 124.2(6) . . ?
O1 N5 O2 119.9(7) . . ?
O2 N5 N6 115.8(7) . . ?
N5 N6 C3 117.3(6) . . ?
C3 N7 C4 102.4(5) . . ?
O3 N8 C4 117.9(7) . . ?
O3 N8 O4 123.9(7) . . ?
O4 N8 C4 118.2(7) . . ?
C4 N9 N10 98.8(5) . . ?
C3 N10 C5 127.2(6) . . ?
N9 N10 C3 111.4(5) . . ?
N9 N10 C5 121.5(5) . . ?
O5 N11 C5 115.9(7) . . ?
O6 N11 C5 116.4(8) . . ?
O6 N11 O5 127.5(9) . . ?
O7 N12 C5 116.1(9) . . ?
O7 N12 O8 129.3(9) . . ?
O8 N12 C5 114.5(8) . . ?
O9 N13 C5 117.5(7) . . ?
O9 N13 O10 127.9(8) . . ?
O10 N13 C5 114.5(8) . . ?
N19 C8 N23 114.7(6) . . ?
N20 C8 N19 136.4(6) . . ?
N20 C8 N23 108.9(6) . . ?
N20 C9 N21 121.0(6) . . ?
N22 C9 N20 118.9(6) . . ?
N22 C9 N21 120.1(6) . . ?
N23 C10 N24 112.1(6) . . ?
N23 C10 N25 112.0(8) . . ?
N23 C10 N26 109.6(6) . . ?
N24 C10 N26 105.9(6) . . ?
N25 C10 N24 111.0(8) . . ?
N25 C10 N26 106.0(5) . . ?
O11 N18 N19 123.0(6) . . ?
O12 N18 N19 116.7(7) . . ?
O12 N18 O11 120.4(7) . . ?
N18 N19 C8 117.5(6) . . ?
C8 N20 C9 102.5(5) . . ?
O13 N21 C9 116.2(6) . . ?
O14 N21 C9 117.9(7) . . ?
O14 N21 O13 125.9(7) . . ?
C9 N22 N23 99.8(5) . . ?
C8 N23 N22 109.9(6) . . ?
C10 N23 C8 127.7(6) . . ?
C10 N23 N22 122.3(6) . . ?
O17 N24 C10 116.8(8) . . ?
O17 N24 O18 124.5(9) . . ?
O18 N24 C10 118.0(8) . . ?
O15 N25 C10 116.3(10) . . ?
O15 N25 O16 129.9(12) . . ?
O16 N25 C10 113.7(13) . . ?
O19 N26 C10 116.4(7) . . ?
O19 N26 O20 128.5(8) . . ?
O20 N26 C10 115.1(7) . . ?
N15 C6 H6 124.9 . . ?
N16 C6 H6 124.9 . . ?
N16 C6 N15 110.2(8) . . ?
N15 C7 H7 126.5 . . ?
N17 C7 H7 126.5 . . ?
N17 C7 N15 107.1(7) . . ?
H14A N14 H14B 109.4 . . ?
N15 N14 H14A 110.0 . . ?
N15 N14 H14B 109.3 . . ?
C6 N15 N14 130.0(7) . . ?
C7 N15 C6 106.5(7) . . ?
C7 N15 N14 123.5(7) . . ?
C6 N16 N17 103.3(7) . . ?
C7 N17 N16 113.0(7) . . ?
C7 N17 H17 130(6) . . ?
N16 N17 H17 117(6) . . ?
N2 C1 H1 124.3 . . ?
N3 C1 H1 124.3 . . ?
N3 C1 N2 111.3(9) . . ?
N2 C2 H2 126.8 . . ?
N2 C2 N4 106.4(9) . . ?
N4 C2 H2 126.8 . . ?
H1A N1 H1B 109.2 . . ?
N2 N1 H1A 108.4 . . ?
N2 N1 H1B 110.3 . . ?
C1 N2 N1 128.5(8) . . ?
C2 N2 C1 108.2(8) . . ?
C2 N2 N1 123.3(8) . . ?
C1 N3 N4 101.8(7) . . ?
C2 N4 N3 112.2(8) . . ?
C2 N4 H4 123.9 . . ?
N3 N4 H4 123.9 . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 1(3)
2 0(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_a
_database_code_depnum_ccdc_archive 'CCDC 1502834'
_audit_update_record             
;
2016-12-26 deposited with the CCDC.
2017-07-12 downloaded from the CCDC.
;
_audit_creation_date             2016-12-23
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2016.12.12 svn.r3370 for OlexSys, GUI svn.r5282)
;
_shelxl_version_number           2014-3
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C3 N9 O10, C H4 N5'
_chemical_formula_sum            'C4 H4 N14 O10'
_chemical_formula_weight         408.21
_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'
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      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   12.264(5)
_cell_length_b                   20.048(7)
_cell_length_c                   12.605(5)
_cell_angle_alpha                90
_cell_angle_beta                 98.056(17)
_cell_angle_gamma                90
_cell_volume                     3069(2)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    1434
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      24.927
_cell_measurement_theta_min      2.396
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.169
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.4587
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2008/1 (Bruker,2008) was used for absorption correction. wR2(int) was 0.1637 before and 0.0766 after correction. The Ratio of minimum to maximum transmission is 0.6152. The λ/2 correction factor is 0.0015.'
_exptl_crystal_colour            'clear whiteish colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.767
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1648
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0942
_diffrn_reflns_av_unetI/netI     0.0991
_diffrn_reflns_Laue_measured_fraction_full 0.961
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            8923
_diffrn_reflns_point_group_measured_fraction_full 0.961
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.003
_diffrn_reflns_theta_min         1.961
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.961
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega 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                1494
_reflns_number_total             2668
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'SIR2004 (Burla et al., 2007)'
_refine_diff_density_max         0.344
_refine_diff_density_min         -0.222
_refine_diff_density_rms         0.058
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     317
_refine_ls_number_reflns         2668
_refine_ls_number_restraints     132
_refine_ls_R_factor_all          0.1142
_refine_ls_R_factor_gt           0.0534
_refine_ls_restrained_S_all      0.995
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0595P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1195
_refine_ls_wR_factor_ref         0.1469
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Rigid bond restraints
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
2. Uiso/Uaniso restraints and constraints
Uanis(N12A) \\sim Ueq, Uanis(N13A) \\sim Ueq, Uanis(N14A) \\sim Ueq: with sigma
of 0.005 and sigma for terminal atoms of 0.01
Uanis(O9A) \\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.01
Uanis(O5A) \\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.01
Uanis(N12) \\sim Ueq, Uanis(N13) \\sim Ueq, Uanis(N14) \\sim Ueq: with sigma of
0.005 and sigma for terminal atoms of 0.01
3. Others
 Sof(N14A)=Sof(N13A)=Sof(N12A)=1-FVAR(1)
 Sof(N14)=Sof(N12)=Sof(N13)=FVAR(1)
 Sof(O9A)=1-FVAR(2)
 Sof(O9)=FVAR(2)
 Sof(O5A)=1-FVAR(3)
 Sof(O5)=FVAR(3)
;
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_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
O4 O 0.62275(19) 0.20716(12) 0.73619(18) 0.0530(7) Uani 1 1 d . U . . .
O3 O 0.7369(2) 0.28167(12) 0.81051(18) 0.0622(8) Uani 1 1 d . U . . .
N2 N 0.75187(19) 0.39915(13) 0.7150(2) 0.0376(6) Uani 1 1 d . U . . .
N5 N 0.6346(2) 0.30117(14) 0.6498(2) 0.0413(7) Uani 1 1 d . U . . .
N6 N 0.6671(2) 0.26364(15) 0.7345(2) 0.0418(7) Uani 1 1 d . U . . .
N3 N 0.6483(2) 0.39944(14) 0.5572(2) 0.0408(7) Uani 1 1 d . U . . .
N4 N 0.7013(2) 0.46061(14) 0.5637(2) 0.0448(7) Uani 1 1 d . U . . .
O1 O 0.8696(2) 0.50711(14) 0.7951(2) 0.0775(9) Uani 1 1 d . U . . .
N10 N 0.3354(3) 0.18504(17) 0.5285(3) 0.0542(8) Uani 1 1 d . U . . .
N1 N 0.8312(2) 0.51039(16) 0.7007(3) 0.0529(8) Uani 1 1 d . U . . .
N8 N 0.5780(3) 0.43445(19) 0.3788(2) 0.0578(9) Uani 1 1 d . U . . .
O2 O 0.8479(3) 0.55418(16) 0.6405(3) 0.0871(10) Uani 1 1 d . U . . .
N7 N 0.6114(3) 0.31311(18) 0.4201(3) 0.0645(9) Uani 1 1 d . U . . .
C2 C 0.6810(2) 0.36230(17) 0.6491(2) 0.0358(7) Uani 1 1 d . U . . .
C4 C 0.4177(2) 0.15688(16) 0.4923(2) 0.0378(8) Uani 1 1 d . U . . .
C1 C 0.7587(2) 0.45540(16) 0.6583(3) 0.0385(8) Uani 1 1 d . U . . .
N9 N 0.4556(3) 0.37327(19) 0.4822(3) 0.0669(10) Uani 1 1 d . U . . .
C3 C 0.5768(3) 0.38052(17) 0.4648(2) 0.0435(8) Uani 1 1 d . U . . .
O6 O 0.7072(2) 0.30384(15) 0.4273(3) 0.0803(9) Uani 1 1 d . U . . .
O5 O 0.5368(3) 0.2738(2) 0.3889(3) 0.0967(17) Uani 0.859(8) 1 d . U P A 1
O7 O 0.6386(3) 0.4237(2) 0.3150(3) 0.1045(12) Uani 1 1 d . U . . .
O8 O 0.5195(3) 0.48089(18) 0.3844(2) 0.0925(11) Uani 1 1 d . U . . .
O9 O 0.3882(3) 0.3715(4) 0.3986(4) 0.102(3) Uani 0.821(14) 1 d . U P B 1
O10 O 0.4348(2) 0.37665(16) 0.5698(3) 0.0841(9) Uani 1 1 d . U . . .
N11 N 0.4193(2) 0.12932(15) 0.3974(2) 0.0468(8) Uani 1 1 d . U . . .
N14 N 0.5186(11) 0.1460(8) 0.5471(9) 0.042(2) Uani 0.63(4) 1 d . U P C 1
N12 N 0.5211(8) 0.0993(8) 0.3976(10) 0.052(2) Uani 0.63(4) 1 d . U P C 1
N13 N 0.5821(7) 0.1125(8) 0.4847(9) 0.054(3) Uani 0.63(4) 1 d . U P C 1
N14A N 0.5266(17) 0.1616(11) 0.5313(18) 0.040(4) Uani 0.37(4) 1 d . U P C 2
N13A N 0.5865(12) 0.1364(13) 0.4614(15) 0.054(4) Uani 0.37(4) 1 d . U P C 2
N12A N 0.5238(13) 0.1209(12) 0.3746(14) 0.047(4) Uani 0.37(4) 1 d . U P C 2
H10A H 0.339(3) 0.1916(19) 0.601(4) 0.068(12) Uiso 1 1 d . . . . .
H10B H 0.268(4) 0.179(2) 0.490(4) 0.101(17) Uiso 1 1 d . . . . .
H11 H 0.362(3) 0.122(2) 0.340(3) 0.079(13) Uiso 1 1 d . . . . .
H14 H 0.557(5) 0.166(3) 0.615(5) 0.13(2) Uiso 1 1 d . . . . .
O9A O 0.417(2) 0.3226(18) 0.432(2) 0.109(8) Uani 0.179(14) 1 d . U P B 2
O5A O 0.580(2) 0.3140(12) 0.3153(17) 0.082(7) Uani 0.141(8) 1 d . U P A 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O4 N6 1.257(3) . ?
O3 N6 1.246(3) . ?
N2 C2 1.337(4) . ?
N2 C1 1.344(4) . ?
N5 N6 1.321(4) . ?
N5 C2 1.352(4) . ?
N3 N4 1.385(4) . ?
N3 C2 1.389(4) . ?
N3 C3 1.408(4) . ?
N4 C1 1.302(4) . ?
O1 N1 1.220(4) . ?
N10 C4 1.295(4) . ?
N10 H10A 0.92(4) . ?
N10 H10B 0.91(5) . ?
N1 O2 1.197(4) . ?
N1 C1 1.468(4) . ?
N8 C3 1.533(5) . ?
N8 O7 1.189(4) . ?
N8 O8 1.184(4) . ?
N7 C3 1.547(5) . ?
N7 O6 1.180(4) . ?
N7 O5 1.230(5) . ?
N7 O5A 1.32(2) . ?
C4 N11 1.319(4) . ?
C4 N14 1.348(12) . ?
C4 N14A 1.36(2) . ?
N9 C3 1.539(5) . ?
N9 O9 1.245(5) . ?
N9 O10 1.169(4) . ?
N9 O9A 1.25(2) . ?
N11 N12 1.386(10) . ?
N11 N12A 1.364(16) . ?
N11 H11 0.94(4) . ?
N14 N13 1.360(14) . ?
N14 H14 1.00(6) . ?
N12 N13 1.267(11) . ?
N14A N13A 1.32(3) . ?
N14A H14 1.07(6) . ?
N13A N12A 1.284(19) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 N2 C1 102.5(3) . . ?
N6 N5 C2 116.2(3) . . ?
O4 N6 N5 116.4(3) . . ?
O3 N6 O4 120.0(3) . . ?
O3 N6 N5 123.6(3) . . ?
N4 N3 C2 110.3(2) . . ?
N4 N3 C3 121.4(2) . . ?
C2 N3 C3 128.3(3) . . ?
C1 N4 N3 99.9(2) . . ?
C4 N10 H10A 119(2) . . ?
C4 N10 H10B 117(3) . . ?
H10A N10 H10B 118(4) . . ?
O1 N1 C1 116.5(3) . . ?
O2 N1 O1 125.6(3) . . ?
O2 N1 C1 118.0(3) . . ?
O7 N8 C3 114.8(3) . . ?
O8 N8 C3 116.5(3) . . ?
O8 N8 O7 128.7(4) . . ?
O6 N7 C3 115.5(3) . . ?
O6 N7 O5 127.8(4) . . ?
O6 N7 O5A 103.2(11) . . ?
O5 N7 C3 116.5(4) . . ?
O5A N7 C3 107.2(10) . . ?
N2 C2 N5 137.2(3) . . ?
N2 C2 N3 108.0(3) . . ?
N5 C2 N3 114.8(3) . . ?
N10 C4 N11 127.9(3) . . ?
N10 C4 N14 126.5(6) . . ?
N10 C4 N14A 128.1(9) . . ?
N11 C4 N14 105.5(6) . . ?
N11 C4 N14A 102.6(9) . . ?
N2 C1 N1 121.1(3) . . ?
N4 C1 N2 119.2(3) . . ?
N4 C1 N1 119.7(3) . . ?
O9 N9 C3 115.0(4) . . ?
O10 N9 C3 118.1(3) . . ?
O10 N9 O9 126.4(4) . . ?
O10 N9 O9A 114.0(13) . . ?
O9A N9 C3 107.8(12) . . ?
N3 C3 N8 109.2(3) . . ?
N3 C3 N7 111.5(3) . . ?
N3 C3 N9 114.2(3) . . ?
N8 C3 N7 109.1(3) . . ?
N8 C3 N9 105.8(3) . . ?
N9 C3 N7 106.8(3) . . ?
C4 N11 N12 107.9(5) . . ?
C4 N11 N12A 112.2(7) . . ?
C4 N11 H11 131(3) . . ?
N12 N11 H11 120(3) . . ?
N12A N11 H11 116(3) . . ?
C4 N14 N13 110.1(8) . . ?
C4 N14 H14 131(3) . . ?
N13 N14 H14 117(3) . . ?
N13 N12 N11 109.5(7) . . ?
N12 N13 N14 106.7(8) . . ?
C4 N14A H14 123(4) . . ?
N13A N14A C4 109.9(15) . . ?
N13A N14A H14 123(4) . . ?
N12A N13A N14A 109.7(15) . . ?
N13A N12A N11 105.0(12) . . ?

_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_a
_database_code_depnum_ccdc_archive 'CCDC 1502830'
_audit_update_record             
;
2016-09-06 deposited with the CCDC.
2017-07-12 downloaded from the CCDC.
;
_audit_creation_date             2016-05-24
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C3 N9 O10, C2 H6 N5'
_chemical_formula_sum            'C5 H6 N14 O10'
_chemical_formula_weight         422.24
_chemical_absolute_configuration ?
_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'
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      orthorhombic
_space_group_IT_number           29
_space_group_name_H-M_alt        'P c a 21'
_space_group_name_Hall           'P 2c -2ac'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y, z'
'-x+1/2, y, z+1/2'

_cell_length_a                   9.2722(11)
_cell_length_b                   13.4860(16)
_cell_length_c                   12.5676(15)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1571.5(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1674
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      20.869
_cell_measurement_theta_min      2.666
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.168
_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            'clear yellowish yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.785
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             856
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.18
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0332
_diffrn_reflns_av_unetI/netI     0.0432
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            8984
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.496
_diffrn_reflns_theta_min         2.666
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.909
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.991
_reflns_number_gt                2425
_reflns_number_total             3474
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_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         0.157
_refine_diff_density_min         -0.193
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   2(2)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.008
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     287
_refine_ls_number_reflns         3474
_refine_ls_number_restraints     7
_refine_ls_R_factor_all          0.0726
_refine_ls_R_factor_gt           0.0432
_refine_ls_restrained_S_all      1.010
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0420P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0818
_refine_ls_wR_factor_ref         0.0927
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: -1(2) 2(2)
2. Uiso/Uaniso restraints and constraints
Uanis(N10) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
;
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_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
C1 C -0.5850(4) -0.7774(3) -0.5856(3) 0.0348(8) Uani 1 1 d . . . . .
C2 C -0.7379(4) -0.7497(3) -0.4678(3) 0.0351(8) Uani 1 1 d . . . . .
C3 C -0.9049(4) -0.8856(3) -0.5272(3) 0.0480(10) Uani 1 1 d . . . . .
N1 N -0.4558(4) -0.7673(2) -0.6499(3) 0.0414(8) Uani 1 1 d . . . . .
N2 N -0.7882(3) -0.6604(2) -0.3195(3) 0.0375(7) Uani 1 1 d . . . . .
N3 N -0.8369(3) -0.7166(2) -0.3967(2) 0.0399(8) Uani 1 1 d . . . . .
N4 N -0.9055(4) -0.9559(3) -0.4305(3) 0.0608(11) Uani 1 1 d . . . . .
N5 N -1.0409(4) -0.8196(3) -0.5230(3) 0.0636(11) Uani 1 1 d . . . . .
N6 N -0.9132(6) -0.9526(4) -0.6259(4) 0.0777(14) Uani 1 1 d . . . . .
N7 N -0.6094(3) -0.7190(2) -0.4999(2) 0.0355(7) Uani 1 1 d . . . . .
N8 N -0.7801(3) -0.8262(2) -0.5335(3) 0.0429(8) Uani 1 1 d . . . . .
N9 N -0.6805(3) -0.8433(2) -0.6123(3) 0.0418(8) Uani 1 1 d . . . . .
O1 O -0.4508(3) -0.8106(2) -0.7345(2) 0.0540(8) Uani 1 1 d . . . . .
O2 O -0.3608(3) -0.7152(3) -0.6155(3) 0.0713(10) Uani 1 1 d . . . . .
O3 O -0.6588(3) -0.6494(3) -0.2979(3) 0.0705(10) Uani 1 1 d . . . . .
O4 O -0.8829(3) -0.61777(19) -0.2642(2) 0.0449(7) Uani 1 1 d . . . . .
O5 O -1.0361(4) -0.7477(3) -0.5813(3) 0.0852(12) Uani 1 1 d . . . . .
O6 O -1.1371(3) -0.8442(3) -0.4651(3) 0.0886(12) Uani 1 1 d . . . . .
O7 O -0.8164(4) -0.9410(3) -0.3635(3) 0.0675(9) Uani 1 1 d . . . . .
O8 O -0.9953(5) -1.0216(3) -0.4360(4) 0.1034(14) Uani 1 1 d . . . . .
O9 O -0.8352(6) -1.0238(4) -0.6230(4) 0.1095(17) Uani 1 1 d . . . . .
O10 O -0.9942(6) -0.9274(5) -0.6939(4) 0.129(2) Uani 1 1 d . . . . .
C4 C -0.2953(4) -0.6188(3) -0.3686(4) 0.0465(10) Uani 1 1 d . . . . .
C5 C -0.2831(4) -0.5231(3) -0.5078(3) 0.0387(9) Uani 1 1 d . . . . .
N10 N -0.3461(5) -0.6750(4) -0.2915(4) 0.0817(16) Uani 1 1 d . U . . .
H10A H -0.434(7) -0.679(4) -0.292(5) 0.093(19) Uiso 1 1 d . . . . .
H10B H -0.282(8) -0.712(4) -0.246(5) 0.12(2) Uiso 1 1 d . . . . .
N11 N -0.3298(5) -0.4719(3) -0.5924(4) 0.0624(12) Uani 1 1 d . . . . .
H11A H -0.271(6) -0.449(4) -0.633(4) 0.060(16) Uiso 1 1 d . . . . .
H11B H -0.418(5) -0.461(3) -0.597(3) 0.048(13) Uiso 1 1 d . . . . .
N12 N -0.3753(3) -0.5714(3) -0.4408(3) 0.0391(8) Uani 1 1 d . . . . .
H12 H -0.466(7) -0.580(4) -0.444(5) 0.097(19) Uiso 1 1 d . . . . .
N13 N -0.1495(3) -0.5351(3) -0.4790(3) 0.0535(10) Uani 1 1 d . . . . .
N14 N -0.1606(4) -0.5969(3) -0.3907(4) 0.0606(11) Uani 1 1 d . . . . .
H14 H -0.083(6) -0.614(4) -0.355(4) 0.083(17) Uiso 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 1.452(5) . ?
C1 N7 1.353(4) . ?
C1 N9 1.298(4) . ?
C2 N3 1.356(5) . ?
C2 N7 1.325(4) . ?
C2 N8 1.378(5) . ?
C3 N4 1.542(6) . ?
C3 N5 1.544(6) . ?
C3 N6 1.537(6) . ?
C3 N8 1.409(5) . ?
N1 O1 1.213(4) . ?
N1 O2 1.207(4) . ?
N2 N3 1.311(4) . ?
N2 O3 1.240(4) . ?
N2 O4 1.259(4) . ?
N4 O7 1.197(5) . ?
N4 O8 1.218(5) . ?
N5 O5 1.216(5) . ?
N5 O6 1.198(5) . ?
N6 O9 1.203(7) . ?
N6 O10 1.187(7) . ?
N8 N9 1.373(4) . ?
C4 N10 1.317(6) . ?
C4 N12 1.335(5) . ?
C4 N14 1.313(5) . ?
C5 N11 1.340(5) . ?
C5 N12 1.365(5) . ?
C5 N13 1.300(5) . ?
N10 H10A 0.82(6) . ?
N10 H10B 0.96(7) . ?
N11 H11A 0.81(5) . ?
N11 H11B 0.83(4) . ?
N12 H12 0.85(6) . ?
N13 N14 1.392(5) . ?
N14 H14 0.88(5) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N7 C1 N1 121.8(3) . . ?
N9 C1 N1 118.9(3) . . ?
N9 C1 N7 119.3(3) . . ?
N3 C2 N8 116.7(3) . . ?
N7 C2 N3 134.9(3) . . ?
N7 C2 N8 107.9(3) . . ?
N4 C3 N5 108.9(3) . . ?
N6 C3 N4 105.9(3) . . ?
N6 C3 N5 109.0(4) . . ?
N8 C3 N4 113.4(3) . . ?
N8 C3 N5 110.2(3) . . ?
N8 C3 N6 109.3(3) . . ?
O1 N1 C1 118.3(4) . . ?
O2 N1 C1 117.2(3) . . ?
O2 N1 O1 124.5(3) . . ?
O3 N2 N3 124.4(3) . . ?
O3 N2 O4 119.9(3) . . ?
O4 N2 N3 115.7(3) . . ?
N2 N3 C2 116.4(3) . . ?
O7 N4 C3 116.6(3) . . ?
O7 N4 O8 129.3(4) . . ?
O8 N4 C3 114.0(4) . . ?
O5 N5 C3 114.2(4) . . ?
O6 N5 C3 118.0(4) . . ?
O6 N5 O5 127.9(5) . . ?
O9 N6 C3 114.5(5) . . ?
O10 N6 C3 116.4(6) . . ?
O10 N6 O9 129.1(6) . . ?
C2 N7 C1 102.1(3) . . ?
C2 N8 C3 128.7(3) . . ?
N9 N8 C2 111.5(3) . . ?
N9 N8 C3 119.8(3) . . ?
C1 N9 N8 99.1(3) . . ?
N10 C4 N12 125.2(4) . . ?
N14 C4 N10 128.7(4) . . ?
N14 C4 N12 106.1(4) . . ?
N11 C5 N12 122.2(4) . . ?
N13 C5 N11 126.3(4) . . ?
N13 C5 N12 111.5(3) . . ?
C4 N10 H10A 113(5) . . ?
C4 N10 H10B 121(4) . . ?
H10A N10 H10B 126(6) . . ?
C5 N11 H11A 119(4) . . ?
C5 N11 H11B 118(3) . . ?
H11A N11 H11B 123(5) . . ?
C4 N12 C5 107.4(3) . . ?
C4 N12 H12 121(4) . . ?
C5 N12 H12 131(4) . . ?
C5 N13 N14 103.0(3) . . ?
C4 N14 N13 111.9(3) . . ?
C4 N14 H14 128(4) . . ?
N13 N14 H14 120(4) . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 -1(2)
2 2(2)

####################################################################### 
# 
# 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_mo_2016281_0m
_database_code_depnum_ccdc_archive 'CCDC 1506809'
_audit_update_record             
;
2017-07-09 deposited with the CCDC.
2017-07-12 downloaded from the CCDC.
;
_audit_creation_date             2017-07-09
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2017.07.04 svn.r3439 for OlexSys, GUI svn.r5361)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C3 N9 O10, H2 O, H5 N2'
_chemical_formula_sum            'C3 H7 N11 O11'
_chemical_formula_weight         373.20
_chemical_absolute_configuration .
_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'
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      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   8.2280(4)
_cell_length_b                   7.3357(3)
_cell_length_c                   11.3167(5)
_cell_angle_alpha                90
_cell_angle_beta                 94.923(3)
_cell_angle_gamma                90
_cell_volume                     680.54(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2730
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.39
_cell_measurement_theta_min      2.48
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.180
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6812
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0505 before and 0.0392 after correction.
The Ratio of minimum to maximum transmission is 0.9136.
The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear whiteish colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.821
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             380
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.2
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0753
_diffrn_reflns_av_unetI/netI     0.0697
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            6258
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.465
_diffrn_reflns_theta_min         1.806
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.821
_reflns_Friedel_fraction_full    0.980
_reflns_Friedel_fraction_max     0.960
_reflns_number_gt                2575
_reflns_number_total             3060
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_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         0.181
_refine_diff_density_min         -0.223
_refine_diff_density_rms         0.052
_refine_ls_abs_structure_details 
;
 Flack x determined using 957 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.0(7)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.956
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         3060
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0505
_refine_ls_R_factor_gt           0.0369
_refine_ls_restrained_S_all      0.956
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0419P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0735
_refine_ls_wR_factor_ref         0.0776
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.5 times of:
  All N(H,H) groups, All N(H,H,H) groups, All O(H,H) groups
2.a Free rotating group:
 O1W(H1WA,H1WB)
;
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_special_details      
;
The structure was solved using Direct Methods (ShelXS). RE = 0.1, Nqual =  -1, Ralpha = 0.063
;
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.1718(3) 0.2560(4) 0.5112(2) 0.0719(7) Uani 1 1 d . . . . .
O1W O 1.0390(2) 1.0594(3) 0.80338(18) 0.0515(5) Uani 1 1 d . . . . .
H1WA H 1.1049 1.0637 0.7496 0.077 Uiso 1 1 d G . . . .
H1WB H 0.9484 1.0155 0.7747 0.077 Uiso 1 1 d G . . . .
O2 O 0.0222(3) 0.4166(4) 0.6211(3) 0.0796(8) Uani 1 1 d . . . . .
O3 O 0.5008(3) 0.4988(4) 0.48172(19) 0.0636(7) Uani 1 1 d . . . . .
O4 O 0.2750(4) 0.6410(3) 0.43071(18) 0.0704(8) Uani 1 1 d . . . A 2
O5 O 0.3992(3) -0.0574(3) 0.8812(2) 0.0574(6) Uani 1 1 d . . . . .
O6 O 0.6186(3) 0.0526(3) 0.97226(18) 0.0505(5) Uani 1 1 d . . . . .
O7 O 0.2106(3) 0.8058(3) 0.62512(19) 0.0600(6) Uani 1 1 d . . . . .
O8 O 0.2161(3) 0.6385(3) 0.78236(17) 0.0549(6) Uani 1 1 d . . . . .
O9 O 0.7382(3) 0.8795(3) 0.7478(2) 0.0581(6) Uani 1 1 d . . . B 1
O10 O 0.7972(3) 0.6439(3) 0.8548(2) 0.0790(9) Uani 1 1 d . . . . .
N1 N 0.1472(3) 0.3783(3) 0.5780(2) 0.0466(6) Uani 1 1 d . . . . .
N2 N 0.3671(3) 0.5518(3) 0.49702(18) 0.0429(6) Uani 1 1 d . . . . .
N3 N 0.2341(3) 0.6674(3) 0.67893(19) 0.0375(5) Uani 1 1 d . . . . .
N4 N 0.4080(3) 0.3992(3) 0.69161(18) 0.0336(5) Uani 1 1 d . . . . .
N5 N 0.3686(3) 0.2356(3) 0.74094(18) 0.0327(5) Uani 1 1 d . . . . .
N6 N 0.5043(3) 0.0578(3) 0.89601(19) 0.0367(5) Uani 1 1 d . . . . .
N7 N 0.6088(3) 0.3485(3) 0.82933(17) 0.0307(5) Uani 1 1 d . . . . .
N8 N 0.5876(3) 0.6386(3) 0.71557(19) 0.0387(5) Uani 1 1 d . . . . .
N9 N 0.7132(3) 0.7194(3) 0.7753(2) 0.0412(6) Uani 1 1 d . . . . .
C1 C 0.2967(3) 0.4968(4) 0.6146(2) 0.0321(6) Uani 1 1 d . . . . .
C2 C 0.5502(3) 0.4698(4) 0.7493(2) 0.0305(5) Uani 1 1 d . . . . .
C3 C 0.4932(3) 0.2169(3) 0.8189(2) 0.0298(5) Uani 1 1 d . . . . .
N10 N 1.0918(3) 0.8173(3) 1.0019(2) 0.0360(5) Uani 1 1 d . . . . .
H10A H 1.082(4) 0.694(5) 0.991(3) 0.054 Uiso 1 1 d R . . . .
H10B H 1.108(4) 0.870(5) 0.929(3) 0.054 Uiso 1 1 d R . . . .
H10C H 1.182(4) 0.848(4) 1.056(3) 0.054 Uiso 1 1 d R . . . .
N11 N 0.9495(3) 0.9038(4) 1.0425(2) 0.0424(6) Uani 1 1 d . . . . .
H11A H 0.953(5) 0.871(5) 1.116(4) 0.064 Uiso 1 1 d R . . . .
H11B H 0.868(5) 0.855(5) 1.003(3) 0.064 Uiso 1 1 d R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 N1 1.201(4) . ?
O2 N1 1.208(4) . ?
O3 N2 1.194(4) . ?
O4 N2 1.211(3) . ?
O5 N6 1.210(3) . ?
O6 N6 1.221(3) . ?
O7 N3 1.191(3) . ?
O8 N3 1.211(3) . ?
O9 N9 1.237(3) . ?
O10 N9 1.220(3) . ?
N1 C1 1.535(3) . ?
N2 C1 1.550(3) . ?
N3 C1 1.558(3) . ?
N4 N5 1.374(3) . ?
N4 C1 1.405(3) . ?
N4 C2 1.390(3) . ?
N5 C3 1.302(3) . ?
N6 C3 1.455(3) . ?
N7 C2 1.331(3) . ?
N7 C3 1.353(3) . ?
N8 N9 1.326(3) . ?
N8 C2 1.339(3) . ?
N10 N11 1.441(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 N1 O2 128.5(3) . . ?
O1 N1 C1 114.7(3) . . ?
O2 N1 C1 116.7(3) . . ?
O3 N2 O4 128.4(3) . . ?
O3 N2 C1 117.2(2) . . ?
O4 N2 C1 114.4(2) . . ?
O7 N3 O8 128.0(3) . . ?
O7 N3 C1 119.5(2) . . ?
O8 N3 C1 112.6(2) . . ?
N5 N4 C1 122.2(2) . . ?
N5 N4 C2 110.69(19) . . ?
C2 N4 C1 125.4(2) . . ?
C3 N5 N4 99.7(2) . . ?
O5 N6 O6 125.0(2) . . ?
O5 N6 C3 118.0(2) . . ?
O6 N6 C3 116.9(2) . . ?
C2 N7 C3 101.96(19) . . ?
N9 N8 C2 117.2(2) . . ?
O9 N9 N8 115.8(2) . . ?
O10 N9 O9 121.4(2) . . ?
O10 N9 N8 122.7(2) . . ?
N1 C1 N2 105.4(2) . . ?
N1 C1 N3 107.0(2) . . ?
N2 C1 N3 110.8(2) . . ?
N4 C1 N1 110.1(2) . . ?
N4 C1 N2 113.2(2) . . ?
N4 C1 N3 110.12(18) . . ?
N7 C2 N4 108.1(2) . . ?
N7 C2 N8 137.2(2) . . ?
N8 C2 N4 114.6(2) . . ?
N5 C3 N6 119.8(2) . . ?
N5 C3 N7 119.4(2) . . ?
N7 C3 N6 120.9(2) . . ?

_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_mo_2016291_0m
_database_code_depnum_ccdc_archive 'CCDC 1506810'
_audit_update_record             
;
2017-07-09 deposited with the CCDC.
2017-07-12 downloaded from the CCDC.
;
_audit_creation_date             2017-07-05
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5361)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C3 N9 O10, H4 N O, H2 O'
_chemical_formula_sum            'C3 H6 N10 O12'
_chemical_formula_weight         374.18
_chemical_absolute_configuration .
_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'
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      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   7.8388(15)
_cell_length_b                   7.8730(15)
_cell_length_c                   10.987(2)
_cell_angle_alpha                90
_cell_angle_beta                 90.413(11)
_cell_angle_gamma                90
_cell_volume                     678.1(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2049
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.381
_cell_measurement_theta_min      2.599
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.184
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5205
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2008/1 (Bruker,2008) was used for absorption correction. wR2(int) was 0.1021 before and 0.0718 after correction. The Ratio of minimum to maximum transmission is 0.6981. The λ/2 correction factor is 0.0015.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.833
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             380
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0417
_diffrn_reflns_av_unetI/netI     0.0694
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            4230
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.205
_diffrn_reflns_theta_min         1.854
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.866
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.988
_reflns_number_gt                2034
_reflns_number_total             2832
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_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         0.219
_refine_diff_density_min         -0.227
_refine_diff_density_rms         0.046
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0(2)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     258
_refine_ls_number_reflns         2832
_refine_ls_number_restraints     71
_refine_ls_R_factor_all          0.0669
_refine_ls_R_factor_gt           0.0426
_refine_ls_restrained_S_all      1.004
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0524P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1068
_refine_ls_wR_factor_ref         0.1210
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 1(2)
 0(2)
2. Fixed Uiso
 At 1.5 times of:
  All N(H,H) groups, All O(H) groups, All O(H,H) groups
3. Restrained distances
 O11A-N10
 1.42 with sigma of 0.02
4. Rigid bond restraints
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
5. Uiso/Uaniso restraints and constraints
Uanis(O1W) \\sim Ueq, Uanis(O1WA) \\sim Ueq: with sigma of 0.005 and sigma for
terminal atoms of 0.01
6. Others
 Sof(O1WA)=Sof(H1WC)=Sof(H1WD)=1-FVAR(1)
 Sof(O1W)=Sof(H1WA)=Sof(H1WB)=FVAR(1)
 Fixed Sof: O11(0.5) H11(0.5) O11A(0.5) H11A(0.5)
7.a Free rotating group:
 O1W(H1WA,H1WB), O1WA(H1WC,H1WD)
7.b Rotating group:
 N10(H10A,H10B)
7.c Tetrahedral OH refined with riding coordinates:
 O11A(H11A)
7.d Idealised tetrahedral OH refined as rotating group:
 O11(H11)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
_atom_sites_special_details      
;
The structure was solved using Direct Methods (ShelXS). RE = 0.3, Nqual =  -1, Ralpha = 0.078
;
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
N3 N 1.3931(3) 1.1807(4) 1.1691(3) 0.0386(7) Uani 1 1 d . U . . .
N2 N 1.6407(4) 1.0790(4) 1.2565(3) 0.0396(7) Uani 1 1 d . U . . .
N7 N 1.7754(4) 1.4938(5) 1.3157(3) 0.0486(8) Uani 1 1 d . U . . .
O1 O 1.6058(4) 0.7889(5) 1.1287(3) 0.0662(9) Uani 1 1 d . U . . .
O2 O 1.3803(4) 0.8907(5) 1.0363(3) 0.0632(9) Uani 1 1 d . U . . .
N4 N 1.6017(4) 1.2381(5) 1.3008(3) 0.0413(7) Uani 1 1 d . U . . .
O4 O 1.2442(5) 1.6792(5) 1.2513(4) 0.0742(10) Uani 1 1 d . U . . .
N6 N 1.6273(5) 1.3725(5) 1.5037(3) 0.0518(9) Uani 1 1 d . U . . .
O5 O 1.7940(4) 1.4772(5) 1.2075(3) 0.0656(9) Uani 1 1 d . U . . .
N8 N 1.4084(4) 1.4579(5) 1.2797(3) 0.0465(8) Uani 1 1 d . U . . .
N1 N 1.4984(4) 0.8996(5) 1.1109(3) 0.0470(8) Uani 1 1 d . U . . .
N9 N 1.2830(4) 1.5325(5) 1.2161(3) 0.0522(9) Uani 1 1 d . U . . .
O3 O 1.2126(5) 1.4684(5) 1.1274(4) 0.0878(14) Uani 1 1 d . U . . .
O8 O 1.7171(5) 1.4520(5) 1.5739(3) 0.0811(11) Uani 1 1 d . U . . .
O9 O 1.8447(5) 1.1035(5) 1.4788(3) 0.0774(11) Uani 1 1 d . U . . .
N10 N 1.0881(4) 2.1393(5) 1.0212(4) 0.0523(9) Uani 1 1 d D U . . .
H10A H 1.1687 2.1716 1.0701 0.078 Uiso 1 1 d GR . . B .
H10B H 1.1370 2.1460 0.9417 0.078 Uiso 1 1 d GR . . . .
O6 O 1.7994(5) 1.6208(5) 1.3761(3) 0.0771(11) Uani 1 1 d . U . . .
N5 N 1.8717(4) 1.2231(5) 1.4119(3) 0.0542(9) Uani 1 1 d . U . . .
O7 O 1.4876(5) 1.3189(6) 1.5206(3) 0.0793(12) Uani 1 1 d . U . . .
C2 C 1.4521(4) 1.2999(5) 1.2450(3) 0.0382(8) Uani 1 1 d . U . . .
O10 O 2.0054(4) 1.2682(6) 1.3674(4) 0.0910(13) Uani 1 1 d . U . . .
C1 C 1.5112(4) 1.0558(5) 1.1820(3) 0.0369(8) Uani 1 1 d . U . . .
C3 C 1.7112(4) 1.3289(5) 1.3798(3) 0.0422(9) Uani 1 1 d . U . . .
O1W O 0.9735(8) 1.8793(12) 1.1787(12) 0.070(3) Uani 0.67(3) 1 d . U P A 1
H1WA H 1.0598 1.8278 1.2080 0.105 Uiso 0.67(3) 1 d G . P A 1
H1WB H 0.9046 1.9029 1.2356 0.105 Uiso 0.67(3) 1 d G . P A 1
O11 O 0.9383(12) 2.2366(12) 1.0144(11) 0.080(3) Uani 0.5 1 d . U P B 1
H11 H 0.8706 2.1912 0.9673 0.120 Uiso 0.5 1 calc GR . P B 1
O11A O 0.9495(12) 2.1793(17) 1.0824(11) 0.098(4) Uani 0.5 1 d D U P B 2
H11A H 0.9335 2.2821 1.0783 0.147 Uiso 0.5 1 calc R . P B 2
H10C H 1.037(11) 2.060(13) 1.077(8) 0.13(3) Uiso 1 1 d . . . . .
O1WA O 0.988(3) 1.929(3) 1.248(3) 0.099(7) Uani 0.33(3) 1 d . U P A 2
H1WC H 0.9491 1.9946 1.3032 0.149 Uiso 0.33(3) 1 d G . P A 2
H1WD H 1.0760 1.8782 1.2753 0.149 Uiso 0.33(3) 1 d G . P A 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N3 C2 1.336(5) . ?
N3 C1 1.357(5) . ?
N2 N4 1.379(5) . ?
N2 C1 1.312(5) . ?
N7 O5 1.206(4) . ?
N7 O6 1.214(5) . ?
N7 C3 1.561(5) . ?
O1 N1 1.226(4) . ?
O2 N1 1.234(4) . ?
N4 C2 1.406(4) . ?
N4 C3 1.411(5) . ?
O4 N9 1.256(5) . ?
N6 O8 1.214(5) . ?
N6 O7 1.190(5) . ?
N6 C3 1.555(5) . ?
N8 N9 1.338(4) . ?
N8 C2 1.346(5) . ?
N1 C1 1.460(5) . ?
N9 O3 1.225(5) . ?
O9 N5 1.214(5) . ?
N10 H10A 0.8645 . ?
N10 H10B 0.9588 . ?
N10 O11 1.404(9) . ?
N10 O11A 1.320(9) . ?
N10 H10C 0.96(9) . ?
N5 O10 1.213(5) . ?
N5 C3 1.547(5) . ?
O1W H1WA 0.8500 . ?
O1W H1WB 0.8500 . ?
O11 H11 0.8200 . ?
O11A H11A 0.8200 . ?
O11A H10C 1.16(9) . ?
O1WA H1WC 0.8500 . ?
O1WA H1WD 0.8500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 N3 C1 102.2(3) . . ?
C1 N2 N4 100.1(3) . . ?
O5 N7 O6 127.5(4) . . ?
O5 N7 C3 113.3(4) . . ?
O6 N7 C3 119.1(3) . . ?
N2 N4 C2 110.3(3) . . ?
N2 N4 C3 122.8(3) . . ?
C2 N4 C3 126.5(3) . . ?
O8 N6 C3 115.1(3) . . ?
O7 N6 O8 127.9(4) . . ?
O7 N6 C3 117.0(4) . . ?
N9 N8 C2 116.5(3) . . ?
O1 N1 O2 125.2(4) . . ?
O1 N1 C1 118.0(3) . . ?
O2 N1 C1 116.8(3) . . ?
O4 N9 N8 114.9(4) . . ?
O3 N9 O4 121.0(4) . . ?
O3 N9 N8 124.0(4) . . ?
H10A N10 H10B 104.7 . . ?
H10A N10 H10C 95.6 . . ?
H10B N10 H10C 142.1 . . ?
O11 N10 H10A 118.7 . . ?
O11 N10 H10B 105.1 . . ?
O11 N10 H10C 92(5) . . ?
O11A N10 H10A 102.4 . . ?
O11A N10 H10B 141.9 . . ?
O11A N10 H10C 59(6) . . ?
O9 N5 C3 114.3(4) . . ?
O10 N5 O9 128.7(4) . . ?
O10 N5 C3 117.0(4) . . ?
N3 C2 N4 108.2(3) . . ?
N3 C2 N8 137.6(3) . . ?
N8 C2 N4 114.2(3) . . ?
N3 C1 N1 120.7(3) . . ?
N2 C1 N3 119.2(3) . . ?
N2 C1 N1 120.1(3) . . ?
N4 C3 N7 109.9(3) . . ?
N4 C3 N6 113.0(3) . . ?
N4 C3 N5 110.9(3) . . ?
N6 C3 N7 110.6(3) . . ?
N5 C3 N7 106.7(3) . . ?
N5 C3 N6 105.5(3) . . ?
H1WA O1W H1WB 109.5 . . ?
N10 O11 H11 109.5 . . ?
N10 O11A H11A 109.5 . . ?
N10 O11A H10C 45(5) . . ?
H11A O11A H10C 151.8 . . ?
H1WC O1WA H1WD 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N2 N4 C2 N3 1.9(4) . . . . ?
N2 N4 C2 N8 -177.5(3) . . . . ?
N2 N4 C3 N7 115.3(4) . . . . ?
N2 N4 C3 N6 -120.6(4) . . . . ?
N2 N4 C3 N5 -2.4(5) . . . . ?
O1 N1 C1 N3 -177.9(4) . . . . ?
O1 N1 C1 N2 4.2(5) . . . . ?
O2 N1 C1 N3 2.8(5) . . . . ?
O2 N1 C1 N2 -175.0(4) . . . . ?
N4 N2 C1 N3 1.4(4) . . . . ?
N4 N2 C1 N1 179.3(3) . . . . ?
O5 N7 C3 N4 -33.7(4) . . . . ?
O5 N7 C3 N6 -159.1(3) . . . . ?
O5 N7 C3 N5 86.7(4) . . . . ?
N9 N8 C2 N3 -9.1(7) . . . . ?
N9 N8 C2 N4 170.1(3) . . . . ?
O8 N6 C3 N7 -55.7(4) . . . . ?
O8 N6 C3 N4 -179.4(4) . . . . ?
O8 N6 C3 N5 59.2(5) . . . . ?
O9 N5 C3 N7 169.2(4) . . . . ?
O9 N5 C3 N4 -71.1(4) . . . . ?
O9 N5 C3 N6 51.6(5) . . . . ?
O6 N7 C3 N4 145.8(4) . . . . ?
O6 N7 C3 N6 20.4(5) . . . . ?
O6 N7 C3 N5 -93.9(4) . . . . ?
O7 N6 C3 N7 127.3(4) . . . . ?
O7 N6 C3 N4 3.6(5) . . . . ?
O7 N6 C3 N5 -117.8(4) . . . . ?
C2 N3 C1 N2 -0.3(4) . . . . ?
C2 N3 C1 N1 -178.2(3) . . . . ?
C2 N4 C3 N7 -56.5(5) . . . . ?
C2 N4 C3 N6 67.5(5) . . . . ?
C2 N4 C3 N5 -174.3(3) . . . . ?
C2 N8 N9 O4 179.4(4) . . . . ?
C2 N8 N9 O3 -2.9(6) . . . . ?
O10 N5 C3 N7 -11.3(5) . . . . ?
O10 N5 C3 N4 108.4(5) . . . . ?
O10 N5 C3 N6 -128.9(4) . . . . ?
C1 N3 C2 N4 -0.9(4) . . . . ?
C1 N3 C2 N8 178.3(5) . . . . ?
C1 N2 N4 C2 -1.9(4) . . . . ?
C1 N2 N4 C3 -175.0(3) . . . . ?
C3 N4 C2 N3 174.6(3) . . . . ?
C3 N4 C2 N8 -4.8(5) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 1(2)
2 0(2)

####################################################################### 
# 
# 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_mo_2016492_0m
_database_code_depnum_ccdc_archive 'CCDC 1506807'
_audit_update_record             
;
2017-07-09 deposited with the CCDC.
2017-07-12 downloaded from the CCDC.
;
_audit_creation_date             2017-07-09
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2017.07.04 svn.r3439 for OlexSys, GUI svn.r5361)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C3 H2 K N9 O11'
_chemical_formula_sum            'C3 H2 K N9 O11'
_chemical_formula_weight         379.24
_chemical_absolute_configuration ad
_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'
K K 0.2009 0.2494 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   7.45940(10)
_cell_length_b                   7.8789(2)
_cell_length_c                   10.4774(2)
_cell_angle_alpha                90
_cell_angle_beta                 90.7450(10)
_cell_angle_gamma                90
_cell_volume                     615.72(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3667
_cell_measurement_temperature    170
_cell_measurement_theta_max      25.521
_cell_measurement_theta_min      2.731
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.526
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6325
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2008/1 (Bruker,2008) was used for absorption correction. wR2(int) was 0.0588 before and 0.0474 after correction. The Ratio of minimum to maximum transmission is 0.8483. The λ/2 correction factor is 0.0015.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.046
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             380
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0281
_diffrn_reflns_av_unetI/netI     0.0310
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            9574
_diffrn_reflns_point_group_measured_fraction_full 0.970
_diffrn_reflns_point_group_measured_fraction_max 0.944
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.532
_diffrn_reflns_theta_min         1.944
_diffrn_ambient_temperature      170.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.769
_reflns_Friedel_fraction_full    0.937
_reflns_Friedel_fraction_max     0.885
_reflns_number_gt                2482
_reflns_number_total             2684
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_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         0.204
_refine_diff_density_min         -0.204
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details 
;
 Flack x determined using 1005 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.03(2)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_matrix_type           full
_refine_ls_number_parameters     223
_refine_ls_number_reflns         2684
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0298
_refine_ls_R_factor_gt           0.0257
_refine_ls_restrained_S_all      1.033
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0272P)²+0.0218P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0543
_refine_ls_wR_factor_ref         0.0562
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.5 times of:
  All O(H,H) groups
2. Restrained distances
 H1WA-O1W = O1W-H1WB
 0.85 with sigma of 0.02
;
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     ?
_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
K1 K 0.43020(7) 0.55177(7) 0.01961(6) 0.02853(15) Uani 1 1 d . . . . .
O1 O 0.2885(2) 0.2479(3) 0.11153(19) 0.0296(4) Uani 1 1 d . . . . .
O1W O 0.5206(2) 0.8145(3) 0.1703(2) 0.0287(4) Uani 1 1 d D . . . .
H1WA H 0.447(4) 0.863(4) 0.214(3) 0.043 Uiso 1 1 d DR . . . .
H1WB H 0.609(4) 0.809(5) 0.217(3) 0.043 Uiso 1 1 d DR . . . .
O2 O 0.2715(2) 0.0534(3) 0.25757(18) 0.0305(4) Uani 1 1 d . . . A 1
O3 O 0.1467(2) 0.8419(2) 0.03383(19) 0.0298(4) Uani 1 1 d . . . . .
O4 O -0.0882(2) 0.9457(2) 0.12688(19) 0.0287(4) Uani 1 1 d . . . . .
O5 O -0.3566(2) 0.6305(3) 0.4709(2) 0.0342(5) Uani 1 1 d . . . . .
O6 O -0.5295(2) 0.4628(3) 0.3584(2) 0.0402(6) Uani 1 1 d . . . . .
O7 O 0.0119(3) 0.4122(3) 0.5251(2) 0.0361(5) Uani 1 1 d . . . . .
O8 O -0.2331(3) 0.2799(3) 0.57502(19) 0.0350(5) Uani 1 1 d . . . B 2
O9 O -0.3236(2) 0.2628(3) 0.19165(19) 0.0336(5) Uani 1 1 d . . . . .
O10 O -0.2997(2) 0.1086(2) 0.3628(2) 0.0318(5) Uani 1 1 d . . . . .
N1 N 0.2230(2) 0.1909(3) 0.2116(2) 0.0220(5) Uani 1 1 d . . . . .
N2 N 0.0926(3) 0.2692(3) 0.2757(2) 0.0228(5) Uani 1 1 d . . . . .
N3 N 0.1184(2) 0.5467(3) 0.16390(19) 0.0198(4) Uani 1 1 d . . . . .
N4 N 0.0204(3) 0.8322(3) 0.1069(2) 0.0227(5) Uani 1 1 d . . . . .
N5 N -0.1399(3) 0.6528(3) 0.2490(2) 0.0219(5) Uani 1 1 d . . . . .
N6 N -0.1047(3) 0.4921(3) 0.2934(2) 0.0207(5) Uani 1 1 d . . . . .
N7 N -0.1363(3) 0.3587(3) 0.5047(2) 0.0246(5) Uani 1 1 d . . . . .
N8 N -0.3877(3) 0.5095(3) 0.4035(2) 0.0249(5) Uani 1 1 d . . . . .
N9 N -0.2870(2) 0.2383(3) 0.3041(2) 0.0242(5) Uani 1 1 d . . . . .
C1 C 0.0504(3) 0.4278(3) 0.2387(2) 0.0198(5) Uani 1 1 d . . . . .
C2 C -0.0014(3) 0.6730(3) 0.1756(2) 0.0195(5) Uani 1 1 d . . . . .
C3 C -0.2208(3) 0.4022(3) 0.3727(3) 0.0211(5) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
K1 K1 4.0968(3) 2_645 ?
K1 K1 4.0968(3) 2_655 ?
K1 O1 2.9588(18) 2_655 ?
K1 O1 2.793(2) . ?
K1 O1W 2.684(2) . ?
K1 O1W 2.758(2) 2_645 ?
K1 O3 3.1190(19) . ?
K1 O4 3.0760(19) 2_545 ?
K1 O9 2.872(2) 2 ?
K1 O9 3.423(2) 1_655 ?
K1 N3 2.7904(19) . ?
O1 K1 2.9588(18) 2_645 ?
O1 N1 1.247(3) . ?
O1W K1 2.758(2) 2_655 ?
O1W H1WA 0.82(2) . ?
O1W H1WB 0.82(2) . ?
O2 N1 1.238(3) . ?
O3 N4 1.224(3) . ?
O4 K1 3.0760(19) 2 ?
O4 N4 1.226(3) . ?
O5 N8 1.207(3) . ?
O6 N8 1.211(3) . ?
O7 N7 1.200(3) . ?
O8 N7 1.210(3) . ?
O9 K1 3.423(2) 1_455 ?
O9 K1 2.872(2) 2_545 ?
O9 N9 1.221(3) . ?
O10 N9 1.197(3) . ?
N1 N2 1.339(3) . ?
N2 C1 1.344(3) . ?
N3 C1 1.327(3) . ?
N3 C2 1.344(3) . ?
N4 C2 1.457(3) . ?
N5 N6 1.373(3) . ?
N5 C2 1.306(3) . ?
N6 C1 1.394(3) . ?
N6 C3 1.400(3) . ?
N7 C3 1.551(3) . ?
N8 C3 1.542(3) . ?
N9 C3 1.555(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
K1 K1 K1 148.14(3) 2_645 2_655 ?
O1 K1 K1 46.23(4) . 2_645 ?
O1 K1 K1 42.98(4) 2_655 2_655 ?
O1 K1 K1 105.84(4) 2_655 2_645 ?
O1 K1 K1 163.05(5) . 2_655 ?
O1 K1 O1 151.84(6) . 2_655 ?
O1 K1 O3 97.16(5) 2_655 . ?
O1 K1 O3 110.60(5) . . ?
O1 K1 O4 119.92(6) 2_655 2_545 ?
O1 K1 O4 67.92(5) . 2_545 ?
O1 K1 O9 131.27(6) . 2 ?
O1 K1 O9 102.31(5) 2_655 1_655 ?
O1 K1 O9 56.72(5) . 1_655 ?
O1W K1 K1 40.50(4) 2_645 2_645 ?
O1W K1 K1 41.86(5) . 2_655 ?
O1W K1 K1 122.88(5) 2_645 2_655 ?
O1W K1 K1 137.59(5) . 2_645 ?
O1W K1 O1 72.30(6) . 2_655 ?
O1W K1 O1 123.47(6) . . ?
O1W K1 O1 73.88(6) 2_645 . ?
O1W K1 O1 85.25(6) 2_645 2_655 ?
O1W K1 O1W 155.82(3) . 2_645 ?
O1W K1 O3 64.66(5) . . ?
O1W K1 O3 128.89(6) 2_645 . ?
O1W K1 O4 134.70(5) . 2_545 ?
O1W K1 O4 64.73(5) 2_645 2_545 ?
O1W K1 O9 81.59(6) 2_645 1_655 ?
O1W K1 O9 94.26(6) . 1_655 ?
O1W K1 O9 82.78(6) 2_645 2 ?
O1W K1 O9 94.11(6) . 2 ?
O1W K1 N3 84.10(6) . . ?
O1W K1 N3 120.05(6) 2_645 . ?
O3 K1 K1 152.00(4) . 2_645 ?
O3 K1 K1 58.22(3) . 2_655 ?
O3 K1 O9 145.26(5) . 1_655 ?
O4 K1 K1 84.20(4) 2_545 2_645 ?
O4 K1 K1 114.93(4) 2_545 2_655 ?
O4 K1 O3 70.40(5) 2_545 . ?
O4 K1 O9 121.18(5) 2_545 1_655 ?
O9 K1 K1 123.19(5) 2 2_645 ?
O9 K1 K1 43.78(4) 1_655 2_645 ?
O9 K1 K1 55.54(4) 2 2_655 ?
O9 K1 K1 123.85(4) 1_655 2_655 ?
O9 K1 O1 62.00(5) 2 2_655 ?
O9 K1 O3 55.35(6) 2 . ?
O9 K1 O4 63.47(5) 2 2_545 ?
O9 K1 O9 158.74(3) 2 1_655 ?
N3 K1 K1 106.43(5) . 2_655 ?
N3 K1 K1 104.79(5) . 2_645 ?
N3 K1 O1 58.61(6) . . ?
N3 K1 O1 149.33(7) . 2_655 ?
N3 K1 O3 54.15(6) . . ?
N3 K1 O4 64.83(5) . 2_545 ?
N3 K1 O9 101.62(6) . 2 ?
N3 K1 O9 98.65(6) . 1_655 ?
K1 O1 K1 90.79(5) . 2_645 ?
N1 O1 K1 138.86(16) . . ?
N1 O1 K1 119.39(15) . 2_645 ?
K1 O1W K1 97.65(7) . 2_655 ?
K1 O1W H1WA 101(3) 2_655 . ?
K1 O1W H1WA 122(2) . . ?
K1 O1W H1WB 120(3) . . ?
K1 O1W H1WB 111(3) 2_655 . ?
H1WA O1W H1WB 104(3) . . ?
N4 O3 K1 120.80(16) . . ?
N4 O4 K1 131.16(15) . 2 ?
K1 O9 K1 80.68(5) 2_545 1_455 ?
N9 O9 K1 136.44(16) . 1_455 ?
N9 O9 K1 135.10(17) . 2_545 ?
O1 N1 N2 123.4(2) . . ?
O2 N1 O1 121.8(2) . . ?
O2 N1 N2 114.8(2) . . ?
N1 N2 C1 116.9(2) . . ?
C1 N3 K1 131.14(15) . . ?
C1 N3 C2 102.07(19) . . ?
C2 N3 K1 126.79(17) . . ?
O3 N4 O4 125.2(2) . . ?
O3 N4 C2 117.0(2) . . ?
O4 N4 C2 117.7(2) . . ?
C2 N5 N6 99.3(2) . . ?
N5 N6 C1 110.6(2) . . ?
N5 N6 C3 123.4(2) . . ?
C1 N6 C3 125.7(2) . . ?
O7 N7 O8 128.9(2) . . ?
O7 N7 C3 116.4(2) . . ?
O8 N7 C3 114.7(2) . . ?
O5 N8 O6 128.9(2) . . ?
O5 N8 C3 114.0(2) . . ?
O6 N8 C3 117.1(2) . . ?
O9 N9 C3 112.4(2) . . ?
O10 N9 O9 127.7(2) . . ?
O10 N9 C3 119.9(2) . . ?
N2 C1 N6 114.3(2) . . ?
N3 C1 N2 137.5(2) . . ?
N3 C1 N6 108.2(2) . . ?
N3 C2 N4 120.9(2) . . ?
N5 C2 N3 119.7(2) . . ?
N5 C2 N4 119.3(2) . . ?
N6 C3 N7 113.17(19) . . ?
N6 C3 N8 110.7(2) . . ?
N6 C3 N9 109.9(2) . . ?
N7 C3 N9 110.6(2) . . ?
N8 C3 N7 104.7(2) . . ?
N8 C3 N9 107.44(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
K1 O1 N1 O2 -132.5(2) . . . . ?
K1 O1 N1 O2 -0.5(3) 2_645 . . . ?
K1 O1 N1 N2 -178.53(16) 2_645 . . . ?
K1 O1 N1 N2 49.5(3) . . . . ?
K1 O3 N4 O4 173.35(17) . . . . ?
K1 O3 N4 C2 -6.4(3) . . . . ?
K1 O4 N4 O3 83.6(3) 2 . . . ?
K1 O4 N4 C2 -96.6(2) 2 . . . ?
K1 O9 N9 O10 129.9(2) 1_455 . . . ?
K1 O9 N9 O10 -6.4(4) 2_545 . . . ?
K1 O9 N9 C3 -48.8(3) 1_455 . . . ?
K1 O9 N9 C3 174.96(14) 2_545 . . . ?
K1 N3 C1 N2 -1.0(4) . . . . ?
K1 N3 C1 N6 177.35(14) . . . . ?
K1 N3 C2 N4 1.7(3) . . . . ?
K1 N3 C2 N5 -178.67(16) . . . . ?
O1 N1 N2 C1 -9.6(3) . . . . ?
O2 N1 N2 C1 172.3(2) . . . . ?
O3 N4 C2 N3 3.6(3) . . . . ?
O3 N4 C2 N5 -176.1(2) . . . . ?
O4 N4 C2 N3 -176.2(2) . . . . ?
O4 N4 C2 N5 4.2(3) . . . . ?
O5 N8 C3 N6 -68.6(3) . . . . ?
O5 N8 C3 N7 53.7(3) . . . . ?
O5 N8 C3 N9 171.3(2) . . . . ?
O6 N8 C3 N6 111.5(3) . . . . ?
O6 N8 C3 N7 -126.2(2) . . . . ?
O6 N8 C3 N9 -8.6(3) . . . . ?
O7 N7 C3 N6 3.1(3) . . . . ?
O7 N7 C3 N8 -117.6(2) . . . . ?
O7 N7 C3 N9 127.0(2) . . . . ?
O8 N7 C3 N6 -179.5(2) . . . . ?
O8 N7 C3 N8 59.8(3) . . . . ?
O8 N7 C3 N9 -55.6(3) . . . . ?
O9 N9 C3 N6 -41.7(3) . . . . ?
O9 N9 C3 N7 -167.35(18) . . . . ?
O9 N9 C3 N8 78.9(2) . . . . ?
O10 N9 C3 N6 139.6(2) . . . . ?
O10 N9 C3 N7 13.9(3) . . . . ?
O10 N9 C3 N8 -99.9(2) . . . . ?
N1 N2 C1 N3 -12.0(4) . . . . ?
N1 N2 C1 N6 169.7(2) . . . . ?
N5 N6 C1 N2 -178.95(19) . . . . ?
N5 N6 C1 N3 2.3(3) . . . . ?
N5 N6 C3 N7 -118.2(2) . . . . ?
N5 N6 C3 N8 -1.0(3) . . . . ?
N5 N6 C3 N9 117.6(2) . . . . ?
N6 N5 C2 N3 1.1(3) . . . . ?
N6 N5 C2 N4 -179.2(2) . . . . ?
C1 N3 C2 N4 -179.4(2) . . . . ?
C1 N3 C2 N5 0.2(3) . . . . ?
C1 N6 C3 N7 68.6(3) . . . . ?
C1 N6 C3 N8 -174.2(2) . . . . ?
C1 N6 C3 N9 -55.6(3) . . . . ?
C2 N3 C1 N2 -179.8(3) . . . . ?
C2 N3 C1 N6 -1.5(3) . . . . ?
C2 N5 N6 C1 -2.0(2) . . . . ?
C2 N5 N6 C3 -176.1(2) . . . . ?
C3 N6 C1 N2 -5.0(3) . . . . ?
C3 N6 C1 N3 176.2(2) . . . . ?

_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_a
_database_code_depnum_ccdc_archive 'CCDC 1506808'
_audit_update_record             
;
2017-07-09 deposited with the CCDC.
2017-07-12 downloaded from the CCDC.
;
_audit_creation_date             2017-07-09
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2017.07.04 svn.r3439 for OlexSys, GUI svn.r5361)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C3 N9 O10, H2 O, H4 N'
_chemical_formula_sum            'C3 H6 N10 O11'
_chemical_formula_weight         358.18
_chemical_absolute_configuration .
_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'
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      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   7.5643(7)
_cell_length_b                   8.0022(7)
_cell_length_c                   10.6515(10)
_cell_angle_alpha                90
_cell_angle_beta                 91.239(2)
_cell_angle_gamma                90
_cell_volume                     644.60(10)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1424
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      25.107
_cell_measurement_theta_min      3.184
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.184
_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            'clear yellowish yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.845
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             364
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0141
_diffrn_reflns_av_unetI/netI     0.0340
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            3901
_diffrn_reflns_point_group_measured_fraction_full 0.974
_diffrn_reflns_point_group_measured_fraction_max 0.926
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.553
_diffrn_reflns_theta_min         2.693
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.762
_reflns_Friedel_fraction_full    0.945
_reflns_Friedel_fraction_max     0.862
_reflns_number_gt                2298
_reflns_number_total             2752
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_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         0.141
_refine_diff_density_min         -0.175
_refine_diff_density_rms         0.039
_refine_ls_abs_structure_details 
;
 Flack x determined using 856 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.6(8)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         2752
_refine_ls_number_restraints     7
_refine_ls_R_factor_all          0.0482
_refine_ls_R_factor_gt           0.0355
_refine_ls_restrained_S_all      1.023
_refine_ls_shift/su_max          0.008
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0372P)²+0.0561P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0739
_refine_ls_wR_factor_ref         0.0796
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.5 times of:
  All N(H,H,H,H) groups, All O(H,H) groups
2. Restrained distances
 N10-H10A = N10-H10B = N10-H10C = N10-H10D
 0.88 with sigma of 0.02
 O1W-H1WB = O1W-H1WA
 0.85 with sigma of 0.02
;
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     ?
_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
O1 O 0.2168(3) -0.5038(3) -0.1210(3) 0.0510(7) Uani 1 1 d . . . . .
O1W O -0.0253(3) -0.0963(4) -0.1818(3) 0.0561(7) Uani 1 1 d D . . . .
H1WA H 0.056(5) -0.147(6) -0.215(5) 0.084 Uiso 1 1 d DR . . . .
H1WB H -0.122(4) -0.114(7) -0.219(4) 0.084 Uiso 1 1 d DR . . . .
O2 O 0.2391(3) -0.3113(3) -0.2612(3) 0.0543(7) Uani 1 1 d . . . A 1
O3 O 0.3563(3) -1.0886(3) -0.0382(2) 0.0512(6) Uani 1 1 d . . . . .
O4 O 0.5889(3) -1.1902(3) -0.1271(3) 0.0502(6) Uani 1 1 d . . . . .
O5 O 0.8181(3) -0.5182(4) -0.1951(2) 0.0528(7) Uani 1 1 d . . . . .
O6 O 0.8008(3) -0.3722(3) -0.3658(3) 0.0553(7) Uani 1 1 d . . . . .
O7 O 0.7277(4) -0.5409(3) -0.5725(2) 0.0596(8) Uani 1 1 d . . . B 2
O8 O 0.4872(3) -0.6696(4) -0.5231(2) 0.0593(8) Uani 1 1 d . . . . .
O9 O 0.8506(3) -0.8844(3) -0.4695(3) 0.0556(7) Uani 1 1 d . . . . .
O10 O 1.0192(3) -0.7247(4) -0.3545(3) 0.0674(9) Uani 1 1 d . . . . .
N1 N 0.3860(3) -0.7977(3) -0.1664(2) 0.0303(6) Uani 1 1 d . . . . .
N2 N 0.6394(3) -0.9042(3) -0.2492(2) 0.0317(6) Uani 1 1 d . . . . .
N3 N 0.6049(3) -0.7458(3) -0.2941(3) 0.0323(6) Uani 1 1 d . . . . .
N4 N 0.4117(3) -0.5256(3) -0.2780(3) 0.0368(6) Uani 1 1 d . . . . .
N5 N 0.2840(3) -0.4482(3) -0.2168(3) 0.0359(6) Uani 1 1 d . . . . .
N6 N 0.4819(4) -1.0800(3) -0.1094(3) 0.0372(6) Uani 1 1 d . . . . .
N7 N 0.7856(3) -0.4976(4) -0.3063(3) 0.0367(6) Uani 1 1 d . . . . .
N8 N 0.6334(4) -0.6181(3) -0.5025(2) 0.0380(6) Uani 1 1 d . . . . .
N9 N 0.8814(3) -0.7672(4) -0.4019(3) 0.0392(7) Uani 1 1 d . . . . .
N10 N 0.0483(5) 0.1877(4) -0.0397(4) 0.0505(8) Uani 1 1 d D . . . .
H10A H 0.153(4) 0.227(6) -0.059(5) 0.076 Uiso 1 1 d DR . . . .
H10B H -0.001(6) 0.100(5) -0.073(4) 0.076 Uiso 1 1 d DR . . . .
H10C H -0.014(6) 0.263(5) -0.081(4) 0.076 Uiso 1 1 d DR . . . .
H10D H 0.071(6) 0.176(7) 0.037(3) 0.076 Uiso 1 1 d DR . . . .
C1 C 0.4525(4) -0.6816(4) -0.2407(3) 0.0295(6) Uani 1 1 d . . . . .
C2 C 0.5033(4) -0.9233(4) -0.1773(3) 0.0297(7) Uani 1 1 d . . . . .
C3 C 0.7183(4) -0.6594(4) -0.3726(3) 0.0312(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
O1 N5 1.232(4) . ?
O1W H1WA 0.83(3) . ?
O1W H1WB 0.84(2) . ?
O2 N5 1.238(4) . ?
O3 N6 1.231(3) . ?
O4 N6 1.214(3) . ?
O5 N7 1.216(4) . ?
O6 N7 1.194(4) . ?
O7 N8 1.212(4) . ?
O8 N8 1.196(4) . ?
O9 N9 1.202(4) . ?
O10 N9 1.198(4) . ?
N1 C1 1.326(4) . ?
N1 C2 1.347(4) . ?
N2 N3 1.377(4) . ?
N2 C2 1.305(4) . ?
N3 C1 1.395(4) . ?
N3 C3 1.395(4) . ?
N4 N5 1.331(3) . ?
N4 C1 1.344(4) . ?
N6 C2 1.458(4) . ?
N7 C3 1.555(4) . ?
N8 C3 1.548(4) . ?
N9 C3 1.543(4) . ?
N10 H10A 0.88(2) . ?
N10 H10B 0.87(3) . ?
N10 H10C 0.88(2) . ?
N10 H10D 0.84(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
H1WA O1W H1WB 111(5) . . ?
C1 N1 C2 102.3(2) . . ?
C2 N2 N3 99.5(2) . . ?
N2 N3 C1 110.5(2) . . ?
N2 N3 C3 123.3(2) . . ?
C3 N3 C1 125.9(2) . . ?
N5 N4 C1 116.8(3) . . ?
O1 N5 O2 121.4(3) . . ?
O1 N5 N4 123.7(3) . . ?
O2 N5 N4 114.9(3) . . ?
O3 N6 C2 116.7(3) . . ?
O4 N6 O3 125.5(3) . . ?
O4 N6 C2 117.8(3) . . ?
O5 N7 C3 112.7(3) . . ?
O6 N7 O5 127.7(3) . . ?
O6 N7 C3 119.6(3) . . ?
O7 N8 C3 114.8(3) . . ?
O8 N8 O7 128.1(3) . . ?
O8 N8 C3 117.0(3) . . ?
O9 N9 C3 114.3(3) . . ?
O10 N9 O9 129.0(3) . . ?
O10 N9 C3 116.7(3) . . ?
H10A N10 H10B 125(5) . . ?
H10A N10 H10C 97(4) . . ?
H10A N10 H10D 96(4) . . ?
H10B N10 H10C 97(4) . . ?
H10B N10 H10D 113(5) . . ?
H10C N10 H10D 132(5) . . ?
N1 C1 N3 108.2(2) . . ?
N1 C1 N4 137.8(3) . . ?
N4 C1 N3 114.0(3) . . ?
N1 C2 N6 121.2(3) . . ?
N2 C2 N1 119.5(3) . . ?
N2 C2 N6 119.3(3) . . ?
N3 C3 N7 109.9(2) . . ?
N3 C3 N8 113.1(2) . . ?
N3 C3 N9 110.4(2) . . ?
N8 C3 N7 110.7(2) . . ?
N9 C3 N7 107.6(2) . . ?
N9 C3 N8 104.9(2) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
