# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2018

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

data_bwn17037
_database_code_depnum_ccdc_archive 'CCDC 1561563'
_audit_update_record             
;
2018-05-23 deposited with the CCDC.
2018-07-26 downloaded from the CCDC.
;
_audit_creation_date             2017-04-11
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5335)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C6 H2 N18 O4, 2(C H4 O)'
_chemical_formula_sum            'C8 H10 N18 O6'
_chemical_formula_weight         454.34
_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           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   12.368(3)
_cell_length_b                   6.1353(12)
_cell_length_c                   13.010(3)
_cell_angle_alpha                90
_cell_angle_beta                 99.24(3)
_cell_angle_gamma                90
_cell_volume                     974.5(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2585
_cell_measurement_temperature    153(2)
_cell_measurement_theta_max      27.4778
_cell_measurement_theta_min      1.5858
_shelx_estimated_absorpt_T_max   0.983
_shelx_estimated_absorpt_T_min   0.969
_exptl_absorpt_coefficient_mu    0.133
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.7887
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2008)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.548
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             464
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.13
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0407
_diffrn_reflns_av_unetI/netI     0.0364
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            6580
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.477
_diffrn_reflns_theta_min         3.173
_diffrn_ambient_temperature      153(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'multiwire proportional'
_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                1983
_reflns_number_total             2204
_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       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2008)'
_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    'XS (Sheldrick, 2008)'
_refine_diff_density_max         0.206
_refine_diff_density_min         -0.222
_refine_diff_density_rms         0.051
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.136
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     146
_refine_ls_number_reflns         2204
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0621
_refine_ls_R_factor_gt           0.0555
_refine_ls_restrained_S_all      1.136
_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)+(0.0500P)²+0.5428P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1278
_refine_ls_wR_factor_ref         0.1325
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All N(H) groups, All O(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Riding coordinates:
 N2(H2), O3(H3)
2.b Idealised Me refined as rotating group:
 C4(H4A,H4B,H4C)
;
_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
O1 O 0.90177(12) 0.5992(3) 0.73602(13) 0.0438(4) Uani 1 1 d . . . . .
O2 O 0.90758(12) 0.7804(3) 0.59366(13) 0.0425(4) Uani 1 1 d . . . . .
N1 N 0.45199(14) 0.6011(3) 0.76884(13) 0.0317(4) Uani 1 1 d . . . . .
N2 N 0.36432(14) 0.4742(3) 0.75753(13) 0.0316(4) Uani 1 1 d . . . . .
H2 H 0.3342 0.4498 0.8107 0.038 Uiso 1 1 d R . . . .
N3 N 0.34286(14) 0.3745(3) 0.66750(14) 0.0340(4) Uani 1 1 d . . . . .
N4 N 0.41938(14) 0.4375(3) 0.61365(14) 0.0327(4) Uani 1 1 d . . . . .
N5 N 0.57814(12) 0.6688(3) 0.65054(12) 0.0247(3) Uani 1 1 d . . . . .
N6 N 0.67967(13) 0.5972(3) 0.69216(13) 0.0276(4) Uani 1 1 d . . . . .
N7 N 0.68978(12) 0.8649(3) 0.57228(12) 0.0248(4) Uani 1 1 d . . . . .
N8 N 0.49006(12) 0.9265(3) 0.53085(12) 0.0247(3) Uani 1 1 d . . . . .
N9 N 0.85969(13) 0.6989(3) 0.65901(14) 0.0301(4) Uani 1 1 d . . . . .
C1 C 0.48258(15) 0.5719(3) 0.67733(14) 0.0247(4) Uani 1 1 d . . . . .
C2 C 0.58619(14) 0.8279(3) 0.58029(14) 0.0229(4) Uani 1 1 d . . . . .
C3 C 0.74033(14) 0.7220(3) 0.64124(14) 0.0247(4) Uani 1 1 d . . . . .
O3 O 0.73358(12) 0.6362(2) 1.08637(11) 0.0353(4) Uani 1 1 d . . . . .
H3 H 0.7555 0.5261 1.0572 0.042 Uiso 1 1 d R . . . .
C4 C 0.6676(2) 0.7760(4) 1.0146(2) 0.0469(6) Uani 1 1 d . . . . .
H4A H 0.6446 0.9024 1.0519 0.070 Uiso 1 1 calc GR . . . .
H4B H 0.6027 0.6964 0.9811 0.070 Uiso 1 1 calc GR . . . .
H4C H 0.7099 0.8256 0.9616 0.070 Uiso 1 1 calc GR . . . .


_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 N9 1.217(2) . ?
O2 N9 1.219(2) . ?
N1 N2 1.324(2) . ?
N1 C1 1.318(2) . ?
N2 H2 0.8501 . ?
N2 N3 1.310(2) . ?
N3 N4 1.322(2) . ?
N4 C1 1.330(3) . ?
N5 N6 1.358(2) . ?
N5 C1 1.416(2) . ?
N5 C2 1.352(2) . ?
N6 C3 1.322(2) . ?
N7 C2 1.322(2) . ?
N7 C3 1.336(2) . ?
N8 N8 1.258(3) 3_676 ?
N8 C2 1.396(2) . ?
N9 C3 1.464(2) . ?
O3 H3 0.8400 . ?
O3 C4 1.425(3) . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?

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
C1 N1 N2 99.69(16) . . ?
N1 N2 H2 118.1 . . ?
N3 N2 N1 114.75(16) . . ?
N3 N2 H2 126.4 . . ?
N2 N3 N4 106.13(16) . . ?
N3 N4 C1 104.48(16) . . ?
N6 N5 C1 121.39(15) . . ?
C2 N5 N6 109.84(15) . . ?
C2 N5 C1 128.67(16) . . ?
C3 N6 N5 100.11(15) . . ?
C2 N7 C3 100.93(15) . . ?
N8 N8 C2 111.45(19) 3_676 . ?
O1 N9 O2 126.08(18) . . ?
O1 N9 C3 117.76(17) . . ?
O2 N9 C3 116.16(17) . . ?
N1 C1 N4 114.94(17) . . ?
N1 C1 N5 122.50(17) . . ?
N4 C1 N5 122.51(17) . . ?
N5 C2 N8 118.36(16) . . ?
N7 C2 N5 110.78(16) . . ?
N7 C2 N8 130.85(17) . . ?
N6 C3 N7 118.33(16) . . ?
N6 C3 N9 120.26(17) . . ?
N7 C3 N9 121.40(16) . . ?
C4 O3 H3 112.4 . . ?
O3 C4 H4A 109.5 . . ?
O3 C4 H4B 109.5 . . ?
O3 C4 H4C 109.5 . . ?
H4A C4 H4B 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 N9 C3 N6 -15.6(3) . . . . ?
O1 N9 C3 N7 165.80(18) . . . . ?
O2 N9 C3 N6 163.53(19) . . . . ?
O2 N9 C3 N7 -15.0(3) . . . . ?
N1 N2 N3 N4 -0.5(2) . . . . ?
N2 N1 C1 N4 0.0(2) . . . . ?
N2 N1 C1 N5 -177.43(17) . . . . ?
N2 N3 N4 C1 0.4(2) . . . . ?
N3 N4 C1 N1 -0.2(2) . . . . ?
N3 N4 C1 N5 177.15(17) . . . . ?
N5 N6 C3 N7 0.1(2) . . . . ?
N5 N6 C3 N9 -178.51(16) . . . . ?
N6 N5 C1 N1 72.6(3) . . . . ?
N6 N5 C1 N4 -104.6(2) . . . . ?
N6 N5 C2 N7 0.6(2) . . . . ?
N6 N5 C2 N8 -178.36(16) . . . . ?
N8 N8 C2 N5 178.85(19) 3_676 . . . ?
N8 N8 C2 N7 0.1(3) 3_676 . . . ?
C1 N1 N2 N3 0.3(2) . . . . ?
C1 N5 N6 C3 176.28(17) . . . . ?
C1 N5 C2 N7 -175.78(17) . . . . ?
C1 N5 C2 N8 5.3(3) . . . . ?
C2 N5 N6 C3 -0.4(2) . . . . ?
C2 N5 C1 N1 -111.4(2) . . . . ?
C2 N5 C1 N4 71.4(3) . . . . ?
C2 N7 C3 N6 0.2(2) . . . . ?
C2 N7 C3 N9 178.82(17) . . . . ?
C3 N7 C2 N5 -0.5(2) . . . . ?
C3 N7 C2 N8 178.31(19) . . . . ?

_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_bwn17066
_database_code_depnum_ccdc_archive 'CCDC 1561565'
_audit_update_record             
;
2018-05-23 deposited with the CCDC.
2018-07-26 downloaded from the CCDC.
;
_audit_creation_date             2017-04-26
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5335)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C3 H N9 O2), 2(C H9 N6)'
_chemical_formula_sum            'C8 H20 N30 O4'
_chemical_formula_weight         600.54
_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           3
_space_group_name_H-M_alt        'P 1 2 1'
_space_group_name_Hall           'P 2y'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'

_cell_length_a                   11.727(2)
_cell_length_b                   7.3404(15)
_cell_length_c                   13.670(3)
_cell_angle_alpha                90
_cell_angle_beta                 90.36(3)
_cell_angle_gamma                90
_cell_volume                     1176.6(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4292
_cell_measurement_temperature    153(2)
_cell_measurement_theta_max      27.4855
_cell_measurement_theta_min      1.7366
_shelx_estimated_absorpt_T_max   0.986
_shelx_estimated_absorpt_T_min   0.978
_exptl_absorpt_coefficient_mu    0.140
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8427
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2008)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.695
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             620
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0348
_diffrn_reflns_av_unetI/netI     0.0528
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            8524
_diffrn_reflns_point_group_measured_fraction_full 0.966
_diffrn_reflns_point_group_measured_fraction_max 0.950
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.487
_diffrn_reflns_theta_min         1.490
_diffrn_ambient_temperature      153(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'multiwire proportional'
_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         0.780
_reflns_Friedel_fraction_full    0.936
_reflns_Friedel_fraction_max     0.904
_reflns_number_gt                4719
_reflns_number_total             5137
_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       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2008)'
_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    'XS (Sheldrick, 2008)'
_refine_diff_density_max         0.361
_refine_diff_density_min         -0.328
_refine_diff_density_rms         0.078
_refine_ls_abs_structure_details 
;
 Flack x determined using 1659 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.8(10)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.131
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     379
_refine_ls_number_reflns         5137
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0604
_refine_ls_R_factor_gt           0.0532
_refine_ls_restrained_S_all      1.131
_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)+(0.0220P)²+1.3010P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1050
_refine_ls_wR_factor_ref         0.1221
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All N(H) groups, All N(H,H) groups
2.a Riding coordinates:
 N5(H5), N14(H14), N19(H19), N20(H20A,H20B), N21(H21), N22(H22A,H22B),
 N23(H23), N24(H24A,H24B), N25(H25), N26(H26A,H26B), N27(H27), N28(H28A,H28B),
 N29(H29), N30(H30A,H30B)
;
_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
O1 O 0.6582(3) 0.0337(5) 0.7382(3) 0.0348(8) Uani 1 1 d . . . . .
O2 O 0.6404(3) 0.0481(6) 0.8970(3) 0.0421(9) Uani 1 1 d . . . . .
N1 N 0.6920(3) 0.0775(6) 0.8202(3) 0.0303(9) Uani 1 1 d . . . . .
N2 N 0.8386(3) 0.2284(5) 0.9161(3) 0.0205(8) Uani 1 1 d . . . . .
N3 N 0.8621(3) 0.2016(5) 0.7503(3) 0.0235(8) Uani 1 1 d . . . . .
N4 N 0.9532(3) 0.2899(5) 0.7920(3) 0.0207(8) Uani 1 1 d . . . . .
N5 N 1.0119(3) 0.3887(6) 0.9506(2) 0.0232(8) Uani 1 1 d . . . . .
H5 H 1.0660 0.4535 0.9285 0.028 Uiso 1 1 d R . . . .
N6 N 1.1327(3) 0.4397(6) 0.7786(3) 0.0260(9) Uani 1 1 d . . . . .
N7 N 1.2061(4) 0.4653(6) 0.7034(3) 0.0286(9) Uani 1 1 d . . . . .
N8 N 1.1629(4) 0.3903(6) 0.6233(3) 0.0309(9) Uani 1 1 d . . . . .
N9 N 1.0604(4) 0.3120(6) 0.6427(3) 0.0289(9) Uani 1 1 d . . . . .
C1 C 0.8001(4) 0.1725(6) 0.8278(3) 0.0216(9) Uani 1 1 d . . . . .
C2 C 0.9375(4) 0.3053(6) 0.8913(3) 0.0200(9) Uani 1 1 d . . . . .
C3 C 1.0476(4) 0.3469(6) 0.7373(3) 0.0221(9) Uani 1 1 d . . . . .
O3 O 1.0993(4) 0.9660(5) 0.8902(3) 0.0397(9) Uani 1 1 d . . . . .
O4 O 1.2141(3) 0.9863(6) 0.7662(3) 0.0421(10) Uani 1 1 d . . . . .
N10 N 1.1244(4) 0.9387(6) 0.8040(3) 0.0303(9) Uani 1 1 d . . . . .
N11 N 1.0659(3) 0.8143(5) 0.6469(3) 0.0219(8) Uani 1 1 d . . . . .
N12 N 0.9441(3) 0.7887(5) 0.7785(2) 0.0223(8) Uani 1 1 d . . . . .
N13 N 0.8994(3) 0.7076(5) 0.6966(2) 0.0196(8) Uani 1 1 d . . . . .
N14 N 0.9535(3) 0.6490(5) 0.5313(2) 0.0214(8) Uani 1 1 d . . . . .
H14 H 0.9004 0.5712 0.5241 0.026 Uiso 1 1 d R . . . .
N15 N 0.7487(3) 0.5479(6) 0.6170(3) 0.0271(9) Uani 1 1 d . . . . .
N16 N 0.6490(3) 0.4769(6) 0.6483(3) 0.0307(9) Uani 1 1 d . . . . .
N17 N 0.6371(4) 0.5082(6) 0.7426(3) 0.0314(10) Uani 1 1 d . . . . .
N18 N 0.7285(3) 0.6002(6) 0.7768(3) 0.0269(9) Uani 1 1 d . . . . .
C4 C 1.0422(4) 0.8469(6) 0.7419(3) 0.0223(9) Uani 1 1 d . . . . .
C5 C 0.9736(4) 0.7219(6) 0.6199(3) 0.0199(9) Uani 1 1 d . . . . .
C6 C 0.7922(4) 0.6207(6) 0.6974(3) 0.0200(9) Uani 1 1 d . . . . .
N19 N 0.4399(3) 0.5987(6) 0.8643(3) 0.0313(10) Uani 1 1 d . . . . .
H19 H 0.4891 0.5196 0.8477 0.038 Uiso 1 1 d R . . . .
N20 N 0.4559(4) 0.7837(6) 0.8434(3) 0.0384(11) Uani 1 1 d . . . . .
H20A H 0.4395 0.7993 0.7833 0.046 Uiso 1 1 d R . . . .
H20B H 0.5151 0.8271 0.8710 0.046 Uiso 1 1 d R . . . .
N21 N 0.2948(3) 0.6876(6) 0.9639(3) 0.0280(9) Uani 1 1 d . . . . .
H21 H 0.3245 0.7884 0.9470 0.034 Uiso 1 1 d R . . . .
N22 N 0.1927(3) 0.6476(6) 1.0151(3) 0.0264(9) Uani 1 1 d . . . . .
H22A H 0.1478 0.7340 0.9995 0.032 Uiso 1 1 d R . . . .
H22B H 0.2005 0.6513 1.0769 0.032 Uiso 1 1 d R . . . .
N23 N 0.3297(3) 0.3810(5) 0.9405(3) 0.0267(9) Uani 1 1 d . . . . .
H23 H 0.2830 0.3373 0.9816 0.032 Uiso 1 1 d R . . . .
N24 N 0.3830(4) 0.2470(6) 0.8817(3) 0.0305(9) Uani 1 1 d . . . . .
H24A H 0.3374 0.1768 0.8512 0.037 Uiso 1 1 d R . . . .
H24B H 0.4171 0.1876 0.9265 0.037 Uiso 1 1 d R . . . .
N25 N 0.3342(4) 0.8213(5) 0.5451(3) 0.0324(10) Uani 1 1 d . . . . .
H25 H 0.2753 0.7914 0.5123 0.039 Uiso 1 1 d R . . . .
N26 N 0.3944(4) 0.7020(6) 0.6082(4) 0.0473(13) Uani 1 1 d . . . . .
H26A H 0.3533 0.6781 0.6575 0.057 Uiso 1 1 d R . . . .
H26B H 0.4093 0.6040 0.5777 0.057 Uiso 1 1 d R . . . .
N27 N 0.4336(3) 1.0546(6) 0.6139(3) 0.0304(9) Uani 1 1 d . . . . .
H27 H 0.4794 0.9736 0.6349 0.036 Uiso 1 1 d R . . . .
N28 N 0.4479(4) 1.2452(6) 0.6256(3) 0.0354(10) Uani 1 1 d . . . . .
H28A H 0.4384 1.2606 0.6867 0.043 Uiso 1 1 d R . . . .
H28B H 0.5049 1.2494 0.5876 0.043 Uiso 1 1 d R . . . .
N29 N 0.2863(3) 1.1157(6) 0.5075(3) 0.0279(9) Uani 1 1 d . . . . .
H29 H 0.2642 1.2175 0.5303 0.034 Uiso 1 1 d R . . . .
N30 N 0.1852(4) 1.0497(7) 0.4621(3) 0.0391(11) Uani 1 1 d . . . . .
H30A H 0.1678 1.0958 0.4070 0.047 Uiso 1 1 d R . . . .
H30B H 0.1286 1.0552 0.5006 0.047 Uiso 1 1 d R . . . .
C7 C 0.3540(4) 0.5531(7) 0.9218(3) 0.0234(9) Uani 1 1 d . . . . .
C8 C 0.3498(4) 0.9981(6) 0.5565(3) 0.0246(10) 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 N1 1.230(5) . ?
O2 N1 1.234(5) . ?
N1 C1 1.450(6) . ?
N2 C1 1.350(5) . ?
N2 C2 1.335(6) . ?
N3 N4 1.370(5) . ?
N3 C1 1.305(6) . ?
N4 C2 1.375(5) . ?
N4 C3 1.404(5) . ?
N5 N5 1.380(6) 2_757 ?
N5 H5 0.8500 . ?
N5 C2 1.336(6) . ?
N6 N7 1.358(5) . ?
N6 C3 1.332(6) . ?
N7 N8 1.323(6) . ?
N8 N9 1.360(6) . ?
N9 C3 1.327(6) . ?
O3 N10 1.233(5) . ?
O4 N10 1.225(6) . ?
N10 C4 1.448(6) . ?
N11 C4 1.350(6) . ?
N11 C5 1.329(6) . ?
N12 N13 1.369(5) . ?
N12 C4 1.327(6) . ?
N13 C5 1.370(5) . ?
N13 C6 1.410(5) . ?
N14 N14 1.389(7) 2_756 ?
N14 H14 0.8501 . ?
N14 C5 1.344(5) . ?
N15 N16 1.352(5) . ?
N15 C6 1.322(6) . ?
N16 N17 1.318(6) . ?
N17 N18 1.349(6) . ?
N18 C6 1.330(5) . ?
N19 H19 0.8500 . ?
N19 N20 1.400(6) . ?
N19 C7 1.325(6) . ?
N20 H20A 0.8500 . ?
N20 H20B 0.8498 . ?
N21 H21 0.8501 . ?
N21 N22 1.421(5) . ?
N21 C7 1.339(6) . ?
N22 H22A 0.8502 . ?
N22 H22B 0.8501 . ?
N23 H23 0.8497 . ?
N23 N24 1.418(5) . ?
N23 C7 1.321(6) . ?
N24 H24A 0.8500 . ?
N24 H24B 0.8500 . ?
N25 H25 0.8501 . ?
N25 N26 1.415(6) . ?
N25 C8 1.319(6) . ?
N26 H26A 0.8500 . ?
N26 H26B 0.8500 . ?
N27 H27 0.8501 . ?
N27 N28 1.418(6) . ?
N27 C8 1.321(6) . ?
N28 H28A 0.8499 . ?
N28 H28B 0.8500 . ?
N29 H29 0.8500 . ?
N29 N30 1.420(5) . ?
N29 C8 1.320(6) . ?
N30 H30A 0.8499 . ?
N30 H30B 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
O1 N1 O2 124.9(4) . . ?
O1 N1 C1 117.9(4) . . ?
O2 N1 C1 117.2(4) . . ?
C2 N2 C1 100.8(3) . . ?
C1 N3 N4 100.2(4) . . ?
N3 N4 C2 109.9(4) . . ?
N3 N4 C3 122.3(4) . . ?
C2 N4 C3 127.8(4) . . ?
N5 N5 H5 120.3 2_757 . ?
C2 N5 N5 117.3(4) . 2_757 ?
C2 N5 H5 121.7 . . ?
C3 N6 N7 103.1(4) . . ?
N8 N7 N6 109.1(4) . . ?
N7 N8 N9 110.5(4) . . ?
C3 N9 N8 102.3(4) . . ?
N2 C1 N1 119.8(4) . . ?
N3 C1 N1 120.8(4) . . ?
N3 C1 N2 119.4(4) . . ?
N2 C2 N4 109.8(4) . . ?
N2 C2 N5 127.2(4) . . ?
N5 C2 N4 123.1(4) . . ?
N6 C3 N4 121.2(4) . . ?
N9 C3 N4 123.8(4) . . ?
N9 C3 N6 115.0(4) . . ?
O3 N10 C4 118.3(4) . . ?
O4 N10 O3 124.6(4) . . ?
O4 N10 C4 117.1(4) . . ?
C5 N11 C4 100.7(4) . . ?
C4 N12 N13 99.2(3) . . ?
N12 N13 C5 110.5(4) . . ?
N12 N13 C6 121.8(3) . . ?
C5 N13 C6 127.7(4) . . ?
N14 N14 H14 120.4 2_756 . ?
C5 N14 N14 114.9(4) . 2_756 ?
C5 N14 H14 119.7 . . ?
C6 N15 N16 102.9(4) . . ?
N17 N16 N15 109.8(4) . . ?
N16 N17 N18 109.7(4) . . ?
C6 N18 N17 102.9(4) . . ?
N11 C4 N10 120.4(4) . . ?
N12 C4 N10 120.3(4) . . ?
N12 C4 N11 119.3(4) . . ?
N11 C5 N13 110.3(4) . . ?
N11 C5 N14 126.3(4) . . ?
N14 C5 N13 123.4(4) . . ?
N15 C6 N13 121.0(4) . . ?
N15 C6 N18 114.7(4) . . ?
N18 C6 N13 124.3(4) . . ?
N20 N19 H19 121.1 . . ?
C7 N19 H19 120.3 . . ?
C7 N19 N20 118.0(4) . . ?
N19 N20 H20A 107.3 . . ?
N19 N20 H20B 112.5 . . ?
H20A N20 H20B 123.9 . . ?
N22 N21 H21 131.4 . . ?
C7 N21 H21 108.1 . . ?
C7 N21 N22 120.0(4) . . ?
N21 N22 H22A 104.2 . . ?
N21 N22 H22B 113.4 . . ?
H22A N22 H22B 106.8 . . ?
N24 N23 H23 113.7 . . ?
C7 N23 H23 129.0 . . ?
C7 N23 N24 117.2(4) . . ?
N23 N24 H24A 114.9 . . ?
N23 N24 H24B 98.9 . . ?
H24A N24 H24B 109.5 . . ?
N26 N25 H25 124.2 . . ?
C8 N25 H25 115.3 . . ?
C8 N25 N26 118.0(4) . . ?
N25 N26 H26A 109.1 . . ?
N25 N26 H26B 109.2 . . ?
H26A N26 H26B 109.5 . . ?
N28 N27 H27 125.3 . . ?
C8 N27 H27 116.6 . . ?
C8 N27 N28 117.6(4) . . ?
N27 N28 H28A 103.0 . . ?
N27 N28 H28B 93.4 . . ?
H28A N28 H28B 134.8 . . ?
N30 N29 H29 101.8 . . ?
C8 N29 H29 124.2 . . ?
C8 N29 N30 117.7(4) . . ?
N29 N30 H30A 116.6 . . ?
N29 N30 H30B 111.4 . . ?
H30A N30 H30B 110.3 . . ?
N19 C7 N21 117.8(4) . . ?
N23 C7 N19 121.5(4) . . ?
N23 C7 N21 120.6(4) . . ?
N25 C8 N27 118.7(5) . . ?
N25 C8 N29 120.4(5) . . ?
N29 C8 N27 120.7(4) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 N1 C1 N2 177.8(4) . . . . ?
O1 N1 C1 N3 -3.6(7) . . . . ?
O2 N1 C1 N2 -1.5(7) . . . . ?
O2 N1 C1 N3 177.0(5) . . . . ?
N3 N4 C2 N2 0.3(5) . . . . ?
N3 N4 C2 N5 -178.7(4) . . . . ?
N3 N4 C3 N6 176.9(4) . . . . ?
N3 N4 C3 N9 -4.0(6) . . . . ?
N4 N3 C1 N1 -179.2(4) . . . . ?
N4 N3 C1 N2 -0.7(5) . . . . ?
N5 N5 C2 N2 3.6(6) 2_757 . . . ?
N5 N5 C2 N4 -177.6(4) 2_757 . . . ?
N6 N7 N8 N9 -0.3(5) . . . . ?
N7 N6 C3 N4 179.0(4) . . . . ?
N7 N6 C3 N9 -0.2(5) . . . . ?
N7 N8 N9 C3 0.2(5) . . . . ?
N8 N9 C3 N4 -179.1(4) . . . . ?
N8 N9 C3 N6 0.0(5) . . . . ?
C1 N2 C2 N4 -0.7(5) . . . . ?
C1 N2 C2 N5 178.3(5) . . . . ?
C1 N3 N4 C2 0.2(4) . . . . ?
C1 N3 N4 C3 178.2(4) . . . . ?
C2 N2 C1 N1 179.5(4) . . . . ?
C2 N2 C1 N3 0.9(5) . . . . ?
C2 N4 C3 N6 -5.4(7) . . . . ?
C2 N4 C3 N9 173.6(4) . . . . ?
C3 N4 C2 N2 -177.6(4) . . . . ?
C3 N4 C2 N5 3.4(7) . . . . ?
C3 N6 N7 N8 0.3(5) . . . . ?
O3 N10 C4 N11 179.9(4) . . . . ?
O3 N10 C4 N12 -2.2(6) . . . . ?
O4 N10 C4 N11 0.9(6) . . . . ?
O4 N10 C4 N12 178.7(4) . . . . ?
N12 N13 C5 N11 -1.6(5) . . . . ?
N12 N13 C5 N14 177.7(4) . . . . ?
N12 N13 C6 N15 177.9(4) . . . . ?
N12 N13 C6 N18 -3.9(6) . . . . ?
N13 N12 C4 N10 -177.6(4) . . . . ?
N13 N12 C4 N11 0.3(5) . . . . ?
N14 N14 C5 N11 10.2(6) 2_756 . . . ?
N14 N14 C5 N13 -168.9(3) 2_756 . . . ?
N15 N16 N17 N18 -0.2(6) . . . . ?
N16 N15 C6 N13 178.8(4) . . . . ?
N16 N15 C6 N18 0.5(5) . . . . ?
N16 N17 N18 C6 0.5(5) . . . . ?
N17 N18 C6 N13 -178.8(4) . . . . ?
N17 N18 C6 N15 -0.6(5) . . . . ?
C4 N11 C5 N13 1.6(5) . . . . ?
C4 N11 C5 N14 -177.7(4) . . . . ?
C4 N12 N13 C5 0.8(4) . . . . ?
C4 N12 N13 C6 179.5(4) . . . . ?
C5 N11 C4 N10 176.7(4) . . . . ?
C5 N11 C4 N12 -1.2(5) . . . . ?
C5 N13 C6 N15 -3.5(7) . . . . ?
C5 N13 C6 N18 174.6(4) . . . . ?
C6 N13 C5 N11 179.7(4) . . . . ?
C6 N13 C5 N14 -1.0(7) . . . . ?
C6 N15 N16 N17 -0.1(5) . . . . ?
N20 N19 C7 N21 -6.3(7) . . . . ?
N20 N19 C7 N23 176.3(5) . . . . ?
N22 N21 C7 N19 171.3(4) . . . . ?
N22 N21 C7 N23 -11.3(6) . . . . ?
N24 N23 C7 N19 -12.7(7) . . . . ?
N24 N23 C7 N21 170.0(4) . . . . ?
N26 N25 C8 N27 11.0(7) . . . . ?
N26 N25 C8 N29 -172.2(4) . . . . ?
N28 N27 C8 N25 -179.4(4) . . . . ?
N28 N27 C8 N29 3.8(7) . . . . ?
N30 N29 C8 N25 14.9(6) . . . . ?
N30 N29 C8 N27 -168.4(4) . . . . ?

_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_bwn17077
_database_code_depnum_ccdc_archive 'CCDC 1561564'
_audit_update_record             
;
2018-05-23 deposited with the CCDC.
2018-07-26 downloaded from the CCDC.
;
_audit_creation_date             2017-05-11
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5335)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C6 H2 N18 O4, C H4 O, 2(H4 N), H2 O'
_chemical_formula_sum            'C7 H16 N20 O6'
_chemical_formula_weight         476.40
_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           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   15.406(3)
_cell_length_b                   8.9944(18)
_cell_length_c                   15.496(3)
_cell_angle_alpha                90
_cell_angle_beta                 119.61(3)
_cell_angle_gamma                90
_cell_volume                     1866.9(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5705
_cell_measurement_temperature    153(2)
_cell_measurement_theta_max      27.4778
_cell_measurement_theta_min      1.5115
_shelx_estimated_absorpt_T_max   0.970
_shelx_estimated_absorpt_T_min   0.963
_exptl_absorpt_coefficient_mu    0.145
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8660
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2008)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.695
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             984
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.21
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0479
_diffrn_reflns_av_unetI/netI     0.0527
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            12354
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.478
_diffrn_reflns_theta_min         2.629
_diffrn_ambient_temperature      153(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'multiwire proportional'
_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                3604
_reflns_number_total             4224
_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       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2008)'
_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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.384
_refine_diff_density_min         -0.349
_refine_diff_density_rms         0.070
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.149
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     299
_refine_ls_number_reflns         4224
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0909
_refine_ls_R_factor_gt           0.0742
_refine_ls_restrained_S_all      1.149
_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)+(0.0530P)²+2.3830P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1564
_refine_ls_wR_factor_ref         0.1664
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All N(H) groups, All N(H,H,H,H) groups, All O(H) groups, All O(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Riding coordinates:
 O5(H5), N20(H20A,H20B,H20C,H20D), N9(H9), N10(H10), O7(H7D,H7E), N19(H19A,
 H19B,H19C,H19D)
2.b Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O -0.00934(15) 0.9476(3) 0.11887(15) 0.0316(5) Uani 1 1 d . . . . .
O2 O -0.03386(15) 0.9414(2) 0.24610(16) 0.0307(5) Uani 1 1 d . . . . .
O3 O 0.57523(15) 0.7892(2) 0.29478(14) 0.0296(5) Uani 1 1 d . . . . .
O4 O 0.57828(16) 0.7764(3) 0.15686(16) 0.0377(6) Uani 1 1 d . . . . .
O5 O 0.13478(16) 0.2423(3) -0.34461(15) 0.0316(5) Uani 1 1 d . . . . .
H5 H 0.1497 0.2493 -0.2848 0.038 Uiso 1 1 d R . . . .
N20 N 0.06336(17) 0.7015(3) -0.00956(17) 0.0284(6) Uani 1 1 d . . . . .
H20A H 0.0026 0.7204 -0.0509 0.034 Uiso 1 1 d R . . . .
H20B H 0.0624 0.6989 0.0448 0.034 Uiso 1 1 d R . . . .
H20C H 0.0725 0.6159 -0.0268 0.034 Uiso 1 1 d R . . . .
H20D H 0.1000 0.7710 -0.0111 0.034 Uiso 1 1 d R . . . .
N1 N 0.00891(17) 0.9026(3) 0.20117(17) 0.0239(5) Uani 1 1 d . . . . .
N2 N 0.12697(16) 0.7204(3) 0.19936(16) 0.0195(5) Uani 1 1 d . . . . .
N3 N 0.12966(17) 0.7730(3) 0.34460(16) 0.0217(5) Uani 1 1 d . . . . .
N4 N 0.20293(16) 0.6718(3) 0.35980(16) 0.0196(5) Uani 1 1 d . . . . .
N5 N 0.24641(18) 0.6263(3) 0.52859(17) 0.0261(5) Uani 1 1 d . . . . .
N6 N 0.3248(2) 0.5539(3) 0.60351(18) 0.0316(6) Uani 1 1 d . . . . .
N7 N 0.3834(2) 0.4998(3) 0.57204(18) 0.0326(6) Uani 1 1 d . . . . .
N8 N 0.34712(18) 0.5363(3) 0.47517(17) 0.0283(6) Uani 1 1 d . . . . .
N9 N 0.26058(17) 0.5437(3) 0.26404(16) 0.0212(5) Uani 1 1 d . . . . .
H9 H 0.2930 0.4834 0.3116 0.025 Uiso 1 1 d R . . . .
N10 N 0.24702(16) 0.5184(3) 0.16979(15) 0.0203(5) Uani 1 1 d . . . . .
H10 H 0.2095 0.4495 0.1325 0.024 Uiso 1 1 d R . . . .
N11 N 0.40181(16) 0.6420(3) 0.21965(16) 0.0207(5) Uani 1 1 d . . . . .
N12 N 0.54086(17) 0.7488(3) 0.20894(17) 0.0245(5) Uani 1 1 d . . . . .
N13 N 0.41080(17) 0.6048(3) 0.07778(17) 0.0225(5) Uani 1 1 d . . . . .
N14 N 0.32659(15) 0.5393(3) 0.07062(16) 0.0183(5) Uani 1 1 d . . . . .
N15 N 0.28327(18) 0.4050(3) -0.07989(17) 0.0266(6) Uani 1 1 d . . . . .
N16 N 0.19817(19) 0.3307(3) -0.14415(18) 0.0299(6) Uani 1 1 d . . . . .
N17 N 0.13249(18) 0.3382(3) -0.11395(17) 0.0261(5) Uani 1 1 d . . . . .
N18 N 0.17094(17) 0.4177(3) -0.02890(16) 0.0230(5) Uani 1 1 d . . . . .
C1 C 0.08980(19) 0.7955(3) 0.2498(2) 0.0201(6) Uani 1 1 d . . . . .
C2 C 0.19861(18) 0.6412(3) 0.27167(18) 0.0185(5) Uani 1 1 d . . . . .
C3 C 0.2648(2) 0.6116(3) 0.45381(19) 0.0215(6) Uani 1 1 d . . . . .
C4 C 0.32337(19) 0.5644(3) 0.15622(18) 0.0182(5) Uani 1 1 d . . . . .
C5 C 0.44945(19) 0.6616(3) 0.1673(2) 0.0214(6) Uani 1 1 d . . . . .
C6 C 0.26090(19) 0.4548(3) -0.01242(19) 0.0192(5) Uani 1 1 d . . . . .
C7 C 0.1757(2) 0.3557(4) -0.3724(2) 0.0371(8) Uani 1 1 d . . . . .
H7A H 0.1411 0.3629 -0.4449 0.056 Uiso 1 1 calc GR . . . .
H7B H 0.2467 0.3354 -0.3475 0.056 Uiso 1 1 calc GR . . . .
H7C H 0.1687 0.4497 -0.3445 0.056 Uiso 1 1 calc GR . . . .
O7 O 0.3571(2) 0.9252(3) 0.30875(17) 0.0617(9) Uani 1 1 d . . . . .
H7D H 0.3441 0.9460 0.2508 0.074 Uiso 1 1 d R . . . .
H7E H 0.3275 0.9815 0.3291 0.074 Uiso 1 1 d R . . . .
N19 N 0.50043(17) 0.7434(3) 0.44147(17) 0.0256(5) Uani 1 1 d . . . . .
H19A H 0.4509 0.7960 0.4016 0.031 Uiso 1 1 d R . . . .
H19B H 0.5486 0.7786 0.4944 0.031 Uiso 1 1 d R . . . .
H19C H 0.5329 0.6836 0.4255 0.031 Uiso 1 1 d R . . . .
H19D H 0.4684 0.6978 0.4650 0.031 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 1.231(3) . ?
O2 N1 1.222(3) . ?
O3 N12 1.219(3) . ?
O4 N12 1.227(3) . ?
O5 H5 0.8400 . ?
O5 C7 1.376(4) . ?
N20 H20A 0.8500 . ?
N20 H20B 0.8500 . ?
N20 H20C 0.8499 . ?
N20 H20D 0.8501 . ?
N1 C1 1.456(3) . ?
N2 C1 1.355(4) . ?
N2 C2 1.326(3) . ?
N3 N4 1.377(3) . ?
N3 C1 1.298(3) . ?
N4 C2 1.362(3) . ?
N4 C3 1.397(3) . ?
N5 N6 1.358(3) . ?
N5 C3 1.328(4) . ?
N6 N7 1.313(4) . ?
N7 N8 1.358(3) . ?
N8 C3 1.328(4) . ?
N9 H9 0.8500 . ?
N9 N10 1.388(3) . ?
N9 C2 1.344(3) . ?
N10 H10 0.8501 . ?
N10 C4 1.358(3) . ?
N11 C4 1.319(3) . ?
N11 C5 1.348(4) . ?
N12 C5 1.455(3) . ?
N13 N14 1.379(3) . ?
N13 C5 1.312(3) . ?
N14 C4 1.370(3) . ?
N14 C6 1.404(3) . ?
N15 N16 1.366(3) . ?
N15 C6 1.330(4) . ?
N16 N17 1.310(4) . ?
N17 N18 1.352(3) . ?
N18 C6 1.322(3) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
O7 H7D 0.8399 . ?
O7 H7E 0.8401 . ?
N19 H19A 0.8499 . ?
N19 H19B 0.8500 . ?
N19 H19C 0.8500 . ?
N19 H19D 0.8501 . ?

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
C7 O5 H5 111.8 . . ?
H20A N20 H20B 101.5 . . ?
H20A N20 H20C 103.7 . . ?
H20A N20 H20D 109.4 . . ?
H20B N20 H20C 111.9 . . ?
H20B N20 H20D 112.7 . . ?
H20C N20 H20D 116.2 . . ?
O1 N1 C1 116.9(2) . . ?
O2 N1 O1 125.8(2) . . ?
O2 N1 C1 117.3(2) . . ?
C2 N2 C1 101.1(2) . . ?
C1 N3 N4 100.7(2) . . ?
N3 N4 C3 120.9(2) . . ?
C2 N4 N3 109.4(2) . . ?
C2 N4 C3 129.6(2) . . ?
C3 N5 N6 102.4(2) . . ?
N7 N6 N5 110.1(2) . . ?
N6 N7 N8 109.7(2) . . ?
C3 N8 N7 102.7(2) . . ?
N10 N9 H9 121.7 . . ?
C2 N9 H9 118.7 . . ?
C2 N9 N10 117.1(2) . . ?
N9 N10 H10 122.3 . . ?
C4 N10 N9 114.9(2) . . ?
C4 N10 H10 117.8 . . ?
C4 N11 C5 101.0(2) . . ?
O3 N12 O4 124.4(2) . . ?
O3 N12 C5 116.7(2) . . ?
O4 N12 C5 118.9(2) . . ?
C5 N13 N14 99.7(2) . . ?
N13 N14 C6 121.9(2) . . ?
C4 N14 N13 109.5(2) . . ?
C4 N14 C6 128.5(2) . . ?
C6 N15 N16 102.1(2) . . ?
N17 N16 N15 110.3(2) . . ?
N16 N17 N18 109.4(2) . . ?
C6 N18 N17 103.5(2) . . ?
N2 C1 N1 121.9(2) . . ?
N3 C1 N1 119.6(2) . . ?
N3 C1 N2 118.5(2) . . ?
N2 C2 N4 110.3(2) . . ?
N2 C2 N9 127.4(2) . . ?
N9 C2 N4 122.3(2) . . ?
N5 C3 N4 122.8(3) . . ?
N8 C3 N4 122.2(2) . . ?
N8 C3 N5 115.0(2) . . ?
N10 C4 N14 123.2(2) . . ?
N11 C4 N10 126.2(2) . . ?
N11 C4 N14 110.5(2) . . ?
N11 C5 N12 119.9(2) . . ?
N13 C5 N11 119.2(2) . . ?
N13 C5 N12 120.9(2) . . ?
N15 C6 N14 123.6(2) . . ?
N18 C6 N14 121.7(2) . . ?
N18 C6 N15 114.7(2) . . ?
O5 C7 H7A 109.5 . . ?
O5 C7 H7B 109.5 . . ?
O5 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
H7D O7 H7E 112.4 . . ?
H19A N19 H19B 122.5 . . ?
H19A N19 H19C 126.0 . . ?
H19A N19 H19D 94.4 . . ?
H19B N19 H19C 99.0 . . ?
H19B N19 H19D 100.5 . . ?
H19C N19 H19D 111.6 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 N1 C1 N2 -16.0(4) . . . . ?
O1 N1 C1 N3 162.3(3) . . . . ?
O2 N1 C1 N2 165.0(2) . . . . ?
O2 N1 C1 N3 -16.7(4) . . . . ?
O3 N12 C5 N11 6.6(4) . . . . ?
O3 N12 C5 N13 -175.4(3) . . . . ?
O4 N12 C5 N11 -173.6(3) . . . . ?
O4 N12 C5 N13 4.5(4) . . . . ?
N3 N4 C2 N2 1.3(3) . . . . ?
N3 N4 C2 N9 -178.9(2) . . . . ?
N3 N4 C3 N5 12.2(4) . . . . ?
N3 N4 C3 N8 -167.1(3) . . . . ?
N4 N3 C1 N1 -177.8(2) . . . . ?
N4 N3 C1 N2 0.6(3) . . . . ?
N5 N6 N7 N8 1.0(4) . . . . ?
N6 N5 C3 N4 -179.2(3) . . . . ?
N6 N5 C3 N8 0.2(3) . . . . ?
N6 N7 N8 C3 -0.8(3) . . . . ?
N7 N8 C3 N4 179.7(3) . . . . ?
N7 N8 C3 N5 0.3(4) . . . . ?
N9 N10 C4 N11 -7.2(4) . . . . ?
N9 N10 C4 N14 175.2(2) . . . . ?
N10 N9 C2 N2 -2.2(4) . . . . ?
N10 N9 C2 N4 178.1(2) . . . . ?
N13 N14 C4 N10 177.3(2) . . . . ?
N13 N14 C4 N11 -0.6(3) . . . . ?
N13 N14 C6 N15 14.4(4) . . . . ?
N13 N14 C6 N18 -166.0(3) . . . . ?
N14 N13 C5 N11 0.0(3) . . . . ?
N14 N13 C5 N12 -178.1(2) . . . . ?
N15 N16 N17 N18 0.2(3) . . . . ?
N16 N15 C6 N14 179.9(3) . . . . ?
N16 N15 C6 N18 0.3(3) . . . . ?
N16 N17 N18 C6 0.0(3) . . . . ?
N17 N18 C6 N14 -179.8(2) . . . . ?
N17 N18 C6 N15 -0.2(3) . . . . ?
C1 N2 C2 N4 -0.9(3) . . . . ?
C1 N2 C2 N9 179.3(3) . . . . ?
C1 N3 N4 C2 -1.1(3) . . . . ?
C1 N3 N4 C3 -178.3(2) . . . . ?
C2 N2 C1 N1 178.5(2) . . . . ?
C2 N2 C1 N3 0.2(3) . . . . ?
C2 N4 C3 N5 -164.3(3) . . . . ?
C2 N4 C3 N8 16.3(5) . . . . ?
C2 N9 N10 C4 114.1(3) . . . . ?
C3 N4 C2 N2 178.2(3) . . . . ?
C3 N4 C2 N9 -2.0(4) . . . . ?
C3 N5 N6 N7 -0.7(3) . . . . ?
C4 N11 C5 N12 177.7(3) . . . . ?
C4 N11 C5 N13 -0.4(3) . . . . ?
C4 N14 C6 N15 -161.9(3) . . . . ?
C4 N14 C6 N18 17.7(4) . . . . ?
C5 N11 C4 N10 -177.3(3) . . . . ?
C5 N11 C4 N14 0.6(3) . . . . ?
C5 N13 N14 C4 0.4(3) . . . . ?
C5 N13 N14 C6 -176.6(2) . . . . ?
C6 N14 C4 N10 -6.0(4) . . . . ?
C6 N14 C4 N11 176.0(3) . . . . ?
C6 N15 N16 N17 -0.3(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
