# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry A.
# This journal is © The Royal Society of Chemistry 2017

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

data_tt
_database_code_depnum_ccdc_archive 'CCDC 1534536'
_audit_update_record             
;
2017-02-24 deposited with the CCDC.
2017-09-12 downloaded from the CCDC.
;
_audit_creation_date             2016-11-24
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2016.11.07 svn.r3352 for OlexSys, GUI svn.r5261)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C2 H3 K N10 O3'
_chemical_formula_sum            'C2 H3 K N10 O3'
_chemical_formula_weight         254.24
_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           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                   6.3241(9)
_cell_length_b                   18.197(3)
_cell_length_c                   7.7647(11)
_cell_angle_alpha                90
_cell_angle_beta                 95.544(4)
_cell_angle_gamma                90
_cell_volume                     889.4(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2017
_cell_measurement_temperature    170
_cell_measurement_theta_max      27.406
_cell_measurement_theta_min      2.864
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.615
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.6249
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0746 before and 0.0487 after correction.
The Ratio of minimum to maximum transmission is 0.8382.
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    1.899
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             512
_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
_diffrn_reflns_av_unetI/netI     0.0277
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            2022
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.408
_diffrn_reflns_theta_min         2.238
_diffrn_ambient_temperature      170
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_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         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1673
_reflns_number_total             2022
_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         0.894
_refine_diff_density_min         -1.175
_refine_diff_density_rms         0.300
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.182
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     157
_refine_ls_number_reflns         2022
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0660
_refine_ls_R_factor_gt           0.0547
_refine_ls_restrained_S_all      1.182
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1243P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1672
_refine_ls_wR_factor_ref         0.1818
_refine_special_details          ?
_olex2_refinement_description    
;
;
_atom_sites_solution_hydrogens   difmap
_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
K1 K 0.19195(11) 0.50288(3) 0.70302(7) 0.0232(3) Uani 1 1 d . . . . .
O1W O 0.0867(4) 0.39476(11) 0.4584(3) 0.0258(5) Uani 1 1 d . . . . .
N6 N 0.7209(3) 0.19797(12) 0.6664(3) 0.0149(5) Uani 1 1 d . . . . .
N3 N 0.4666(4) 0.25119(12) 0.7874(3) 0.0192(5) Uani 1 1 d . . . . .
O1 O 0.4862(4) 0.39285(11) 0.7797(3) 0.0311(5) Uani 1 1 d . . . . .
O2 O 0.7117(4) 0.44710(11) 0.6303(3) 0.0319(6) Uani 1 1 d . . . . .
N7 N 1.0236(4) 0.22504(13) 0.5106(3) 0.0180(5) Uani 1 1 d . . . . .
N8 N 1.1485(4) 0.17818(12) 0.4363(3) 0.0190(5) Uani 1 1 d . . . . .
N4 N 0.4495(4) 0.17638(12) 0.7977(3) 0.0207(5) Uani 1 1 d . . . . .
N5 N 0.5980(4) 0.14374(12) 0.7261(3) 0.0189(5) Uani 1 1 d . . . . .
N2 N 0.7317(4) 0.32668(12) 0.6503(3) 0.0193(5) Uani 1 1 d . . . . .
C1 C 0.6369(4) 0.26519(14) 0.7026(3) 0.0154(5) Uani 1 1 d . . . . .
N9 N 1.0987(4) 0.10906(13) 0.4513(3) 0.0205(5) Uani 1 1 d . . . . .
N1 N 0.6367(4) 0.39021(12) 0.6891(3) 0.0202(5) Uani 1 1 d . . . . .
N10 N 0.9303(4) 0.10712(13) 0.5416(3) 0.0201(5) Uani 1 1 d . . . . .
C2 C 0.8925(4) 0.17794(13) 0.5741(3) 0.0148(5) Uani 1 1 d . . . . .
H1WA H 0.015(7) 0.353(3) 0.496(5) 0.058(14) Uiso 1 1 d . . . . .
H1WB H 0.193(6) 0.378(2) 0.403(5) 0.032(9) Uiso 1 1 d . . . . .
H8 H 1.248(9) 0.201(3) 0.386(7) 0.071(15) 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
K1 K1 3.7902(14) 3_566 ?
K1 O1W 2.778(2) 3_566 ?
K1 O1W 2.771(2) . ?
K1 O1 2.759(2) . ?
K1 O2 2.864(2) 3_666 ?
K1 O2 3.200(3) 1_455 ?
K1 N5 2.915(2) 2_656 ?
K1 N9 2.904(2) 4_466 ?
K1 N10 2.902(2) 2_656 ?
O1W K1 2.778(2) 3_566 ?
O1W H1WA 0.94(5) . ?
O1W H1WB 0.89(4) . ?
N6 N5 1.365(3) . ?
N6 C1 1.374(3) . ?
N6 C2 1.405(3) . ?
N3 N4 1.368(3) . ?
N3 C1 1.340(3) . ?
O1 N1 1.238(3) . ?
O2 K1 3.200(3) 1_655 ?
O2 K1 2.864(2) 3_666 ?
O2 N1 1.244(3) . ?
N7 N8 1.331(3) . ?
N7 C2 1.320(3) . ?
N8 N9 1.304(3) . ?
N8 H8 0.88(5) . ?
N4 N5 1.283(3) . ?
N5 K1 2.915(2) 2_646 ?
N2 C1 1.350(3) . ?
N2 N1 1.350(3) . ?
N9 K1 2.904(2) 4_665 ?
N9 N10 1.331(3) . ?
N10 K1 2.902(2) 2_646 ?
N10 C2 1.339(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
O1W K1 K1 46.84(5) 3_566 3_566 ?
O1W K1 K1 47.00(5) . 3_566 ?
O1W K1 O1W 93.84(6) . 3_566 ?
O1W K1 O2 65.38(6) 3_566 1_455 ?
O1W K1 O2 63.91(6) 3_566 3_666 ?
O1W K1 O2 59.52(6) . 1_455 ?
O1W K1 O2 70.38(6) . 3_666 ?
O1W K1 N5 145.98(6) . 2_656 ?
O1W K1 N5 75.72(7) 3_566 2_656 ?
O1W K1 N9 84.62(6) . 4_466 ?
O1W K1 N9 127.53(7) 3_566 4_466 ?
O1W K1 N10 150.48(7) . 2_656 ?
O1W K1 N10 70.78(6) 3_566 2_656 ?
O1 K1 K1 121.59(5) . 3_566 ?
O1 K1 O1W 165.70(7) . 3_566 ?
O1 K1 O1W 75.22(7) . . ?
O1 K1 O2 103.16(6) . 3_666 ?
O1 K1 O2 114.62(6) . 1_455 ?
O1 K1 N5 108.17(7) . 2_656 ?
O1 K1 N9 61.56(6) . 4_466 ?
O1 K1 N10 123.07(7) . 2_656 ?
O2 K1 K1 55.40(5) 3_666 3_566 ?
O2 K1 K1 47.45(4) 1_455 3_566 ?
O2 K1 O2 102.85(5) 3_666 1_455 ?
O2 K1 N5 76.02(6) 3_666 2_656 ?
O2 K1 N9 153.82(6) 3_666 4_466 ?
O2 K1 N10 120.24(6) 3_666 2_656 ?
N5 K1 K1 115.16(5) 2_656 3_566 ?
N5 K1 O2 136.03(6) 2_656 1_455 ?
N9 K1 K1 112.21(6) 4_466 3_566 ?
N9 K1 O2 69.18(6) 4_466 1_455 ?
N9 K1 N5 127.55(6) 4_466 2_656 ?
N10 K1 K1 113.25(6) 2_656 3_566 ?
N10 K1 O2 90.97(6) 2_656 1_455 ?
N10 K1 N5 56.14(6) 2_656 2_656 ?
N10 K1 N9 85.43(7) 2_656 4_466 ?
K1 O1W K1 86.16(6) . 3_566 ?
K1 O1W H1WA 116(3) . . ?
K1 O1W H1WA 112(3) 3_566 . ?
K1 O1W H1WB 115(2) . . ?
K1 O1W H1WB 119(2) 3_566 . ?
H1WA O1W H1WB 107(4) . . ?
N5 N6 C1 109.3(2) . . ?
N5 N6 C2 118.6(2) . . ?
C1 N6 C2 132.0(2) . . ?
C1 N3 N4 106.8(2) . . ?
N1 O1 K1 116.43(16) . . ?
K1 O2 K1 77.15(5) 3_666 1_655 ?
N1 O2 K1 126.06(18) . 1_655 ?
N1 O2 K1 135.89(17) . 3_666 ?
C2 N7 N8 99.6(2) . . ?
N7 N8 H8 112(4) . . ?
N9 N8 N7 114.9(2) . . ?
N9 N8 H8 133(4) . . ?
N5 N4 N3 111.7(2) . . ?
N6 N5 K1 115.83(15) . 2_646 ?
N4 N5 K1 131.66(15) . 2_646 ?
N4 N5 N6 106.1(2) . . ?
N1 N2 C1 115.0(2) . . ?
N3 C1 N6 106.1(2) . . ?
N3 C1 N2 135.0(2) . . ?
N2 C1 N6 119.0(2) . . ?
N8 N9 K1 123.43(15) . 4_665 ?
N8 N9 N10 106.5(2) . . ?
N10 N9 K1 123.74(16) . 4_665 ?
O1 N1 O2 121.2(2) . . ?
O1 N1 N2 122.9(2) . . ?
O2 N1 N2 115.9(2) . . ?
N9 N10 K1 131.06(17) . 2_646 ?
N9 N10 C2 103.9(2) . . ?
C2 N10 K1 115.87(15) . 2_646 ?
N7 C2 N6 124.4(2) . . ?
N7 C2 N10 115.1(2) . . ?
N10 C2 N6 120.4(2) . . ?

_shelx_SHELXL_version_number     2014/7
_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_2016827_0m
_database_code_depnum_ccdc_archive 'CCDC 1534411'
_audit_update_record             
;
2017-02-23 deposited with the CCDC.
2017-09-12 downloaded from the CCDC.
;
_audit_creation_date             2016-12-15
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2016.11.30 svn.r3356 for OlexSys, GUI svn.r5269)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C2 N10 O2, 2(H2 O), 2(H5 N2)'
_chemical_formula_sum            'C2 H14 N14 O4'
_chemical_formula_weight         298.27
_chemical_absolute_configuration rmad
_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                   3.6735(6)
_cell_length_b                   20.633(4)
_cell_length_c                   7.9016(13)
_cell_angle_alpha                90
_cell_angle_beta                 92.690(4)
_cell_angle_gamma                90
_cell_volume                     598.23(17)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2346
_cell_measurement_temperature    170
_cell_measurement_theta_max      26.026
_cell_measurement_theta_min      2.580
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.146
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6643
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0957 before and 0.0556 after correction.
The Ratio of minimum to maximum transmission is 0.8910.
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    1.656
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             312
_exptl_crystal_preparation       ?
_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  0.0323
_diffrn_reflns_av_unetI/netI     0.0292
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            10026
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.467
_diffrn_reflns_theta_min         1.974
_diffrn_ambient_temperature      170
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_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         0.946
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.996
_reflns_number_gt                2649
_reflns_number_total             2724
_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         0.185
_refine_diff_density_min         -0.257
_refine_diff_density_rms         0.070
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.6(15)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.105
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     238
_refine_ls_number_reflns         2724
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0292
_refine_ls_R_factor_gt           0.0282
_refine_ls_restrained_S_all      1.105
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0404P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0668
_refine_ls_wR_factor_ref         0.0674
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.4(15) 0.6(15)
;
_atom_sites_solution_hydrogens   difmap
_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
O2 O 0.2926(5) 0.66540(7) 0.4366(2) 0.0245(4) Uani 1 1 d . . . . .
O1 O 0.0111(5) 0.59534(7) 0.5891(2) 0.0254(4) Uani 1 1 d . . . . .
O1W O 0.9418(4) 0.31290(7) 0.5135(2) 0.0220(3) Uani 1 1 d . . . . .
O2W O 0.6609(6) 0.27044(10) 0.8071(2) 0.0323(4) Uani 1 1 d . . . . .
N1 N 0.1812(5) 0.60918(8) 0.4587(2) 0.0171(3) Uani 1 1 d . . . . .
N6 N 0.4905(4) 0.52603(8) 0.1047(2) 0.0147(3) Uani 1 1 d . . . . .
N10 N 0.5943(5) 0.42948(8) 0.2709(2) 0.0170(4) Uani 1 1 d . . . . .
N13 N 0.7725(5) 0.71768(9) 0.7043(2) 0.0166(3) Uani 1 1 d . . . . .
N7 N 0.3263(5) 0.41823(8) 0.0140(2) 0.0195(4) Uani 1 1 d . . . . .
N14 N 1.0483(4) 0.72959(8) 0.8381(2) 0.0162(3) Uani 1 1 d . . . . .
N11 N 0.1670(5) 0.44228(9) 0.5747(2) 0.0164(3) Uani 1 1 d . . . . .
N12 N -0.0971(4) 0.46096(9) 0.6960(2) 0.0167(3) Uani 1 1 d . . . . .
N2 N 0.2288(5) 0.56065(8) 0.3523(2) 0.0166(3) Uani 1 1 d . . . . .
N9 N 0.5233(5) 0.36649(8) 0.2392(2) 0.0186(4) Uani 1 1 d . . . . .
N3 N 0.4846(5) 0.63087(9) 0.1308(2) 0.0187(4) Uani 1 1 d . . . . .
N8 N 0.3673(5) 0.35981(9) 0.0873(2) 0.0213(4) Uani 1 1 d . . . . .
N5 N 0.6345(5) 0.55083(9) -0.0367(2) 0.0194(4) Uani 1 1 d . . . . .
N4 N 0.6274(5) 0.61272(8) -0.0190(2) 0.0216(4) Uani 1 1 d . . . . .
C1 C 0.3990(5) 0.57581(9) 0.2078(3) 0.0145(4) Uani 1 1 d . . . . .
C2 C 0.4682(5) 0.45839(9) 0.1306(2) 0.0136(4) Uani 1 1 d . . . . .
H14A H 0.996(7) 0.7697(14) 0.879(3) 0.019(6) Uiso 1 1 d . . . . .
H14B H 1.000(7) 0.6993(14) 0.920(4) 0.020(6) Uiso 1 1 d . . . . .
H11A H 0.404(9) 0.4499(16) 0.612(4) 0.033(7) Uiso 1 1 d . . . . .
H12A H -0.075(7) 0.5020(15) 0.705(3) 0.018(6) Uiso 1 1 d . . . . .
H13A H 0.542(8) 0.7201(13) 0.733(3) 0.021(6) Uiso 1 1 d . . . . .
H11B H 0.126(7) 0.4018(16) 0.539(4) 0.024(7) Uiso 1 1 d . . . . .
H13B H 0.797(8) 0.7435(15) 0.620(4) 0.028(7) Uiso 1 1 d . . . . .
H12B H -0.006(8) 0.4457(16) 0.797(4) 0.029(7) Uiso 1 1 d . . . . .
H1WA H 0.766(9) 0.3207(17) 0.442(4) 0.040(9) Uiso 1 1 d . . . . .
H11C H 0.143(7) 0.4685(14) 0.489(4) 0.025(7) Uiso 1 1 d . . . . .
H13C H 0.812(8) 0.6777(15) 0.663(3) 0.023(7) Uiso 1 1 d . . . . .
H1WB H 0.851(11) 0.2993(18) 0.612(5) 0.050(10) Uiso 1 1 d . . . . .
H2WA H 0.600(10) 0.234(2) 0.814(5) 0.055(11) Uiso 1 1 d . . . . .
H2WB H 0.521(9) 0.2946(19) 0.871(4) 0.042(9) 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
O2 N1 1.245(2) . ?
O1 N1 1.263(2) . ?
O1W H1WA 0.85(3) . ?
O1W H1WB 0.91(4) . ?
O2W H2WA 0.80(4) . ?
O2W H2WB 0.89(4) . ?
N1 N2 1.324(2) . ?
N6 N5 1.359(3) . ?
N6 C1 1.362(3) . ?
N6 C2 1.414(2) . ?
N10 N9 1.347(2) . ?
N10 C2 1.323(3) . ?
N13 N14 1.451(2) . ?
N13 H13A 0.89(3) . ?
N13 H13B 0.86(3) . ?
N13 H13C 0.90(3) . ?
N7 N8 1.343(2) . ?
N7 C2 1.328(3) . ?
N14 H14A 0.91(3) . ?
N14 H14B 0.92(3) . ?
N11 N12 1.447(2) . ?
N11 H11A 0.92(3) . ?
N11 H11B 0.89(3) . ?
N11 H11C 0.87(3) . ?
N12 H12A 0.85(3) . ?
N12 H12B 0.90(3) . ?
N2 C1 1.364(3) . ?
N9 N8 1.313(3) . ?
N3 N4 1.369(3) . ?
N3 C1 1.333(3) . ?
N5 N4 1.285(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
H1WA O1W H1WB 109(3) . . ?
H2WA O2W H2WB 109(4) . . ?
O2 N1 O1 120.23(17) . . ?
O2 N1 N2 124.15(19) . . ?
O1 N1 N2 115.62(17) . . ?
N5 N6 C1 108.91(17) . . ?
N5 N6 C2 121.22(16) . . ?
C1 N6 C2 129.80(17) . . ?
C2 N10 N9 102.84(16) . . ?
N14 N13 H13A 116.4(18) . . ?
N14 N13 H13B 111.3(19) . . ?
N14 N13 H13C 107.4(18) . . ?
H13A N13 H13B 107(3) . . ?
H13A N13 H13C 108(3) . . ?
H13B N13 H13C 105(3) . . ?
C2 N7 N8 103.21(17) . . ?
N13 N14 H14A 105.0(15) . . ?
N13 N14 H14B 104.3(17) . . ?
H14A N14 H14B 108(2) . . ?
N12 N11 H11A 113.3(19) . . ?
N12 N11 H11B 110.4(19) . . ?
N12 N11 H11C 107.8(19) . . ?
H11A N11 H11B 114(3) . . ?
H11A N11 H11C 102(3) . . ?
H11B N11 H11C 109(3) . . ?
N11 N12 H12A 104.9(18) . . ?
N11 N12 H12B 104.9(19) . . ?
H12A N12 H12B 104(3) . . ?
N1 N2 C1 115.94(17) . . ?
N8 N9 N10 110.10(16) . . ?
C1 N3 N4 105.63(17) . . ?
N9 N8 N7 109.59(16) . . ?
N4 N5 N6 105.90(17) . . ?
N5 N4 N3 112.13(17) . . ?
N6 C1 N2 117.59(17) . . ?
N3 C1 N6 107.44(18) . . ?
N3 C1 N2 134.81(19) . . ?
N10 C2 N6 123.09(16) . . ?
N10 C2 N7 114.26(17) . . ?
N7 C2 N6 122.63(17) . . ?

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
O2 N1 N2 C1 -2.7(3) . . . . ?
O1 N1 N2 C1 177.40(17) . . . . ?
N1 N2 C1 N6 172.57(17) . . . . ?
N1 N2 C1 N3 -12.9(3) . . . . ?
N6 N5 N4 N3 0.4(2) . . . . ?
N10 N9 N8 N7 -0.7(2) . . . . ?
N9 N10 C2 N6 -178.79(17) . . . . ?
N9 N10 C2 N7 -0.3(2) . . . . ?
N8 N7 C2 N6 178.42(17) . . . . ?
N8 N7 C2 N10 0.0(2) . . . . ?
N5 N6 C1 N2 176.10(16) . . . . ?
N5 N6 C1 N3 0.1(2) . . . . ?
N5 N6 C2 N10 128.0(2) . . . . ?
N5 N6 C2 N7 -50.3(3) . . . . ?
N4 N3 C1 N6 0.1(2) . . . . ?
N4 N3 C1 N2 -174.9(2) . . . . ?
C1 N6 N5 N4 -0.3(2) . . . . ?
C1 N6 C2 N10 -48.8(3) . . . . ?
C1 N6 C2 N7 132.9(2) . . . . ?
C1 N3 N4 N5 -0.3(2) . . . . ?
C2 N6 N5 N4 -177.72(16) . . . . ?
C2 N6 C1 N2 -6.8(3) . . . . ?
C2 N6 C1 N3 177.27(18) . . . . ?
C2 N10 N9 N8 0.6(2) . . . . ?
C2 N7 N8 N9 0.4(2) . . . . ?

_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 0.4(15)
2 0.6(15)

####################################################################### 
# 
# 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_2016770_0m
_database_code_depnum_ccdc_archive 'CCDC 1534412'
_audit_update_record             
;
2017-02-23 deposited with the CCDC.
2017-09-12 downloaded from the CCDC.
;
_audit_creation_date             2016-12-02
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2016.11.24 svn.r3356 for OlexSys, GUI svn.r5267)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C2 N10 O2, 2(H4 N O), H2 O'
_chemical_formula_sum            'C2 H10 N12 O5'
_chemical_formula_weight         282.22
_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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.7628(8)
_cell_length_b                   8.4720(9)
_cell_length_c                   8.6864(9)
_cell_angle_alpha                96.566(2)
_cell_angle_beta                 99.093(2)
_cell_angle_gamma                107.015(2)
_cell_volume                     531.54(10)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2650
_cell_measurement_temperature    170
_cell_measurement_theta_max      27.39
_cell_measurement_theta_min      2.41
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.161
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6651
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0603 before and 0.0430 after correction.
The Ratio of minimum to maximum transmission is 0.8920.
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    1.763
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             292
_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  0.0213
_diffrn_reflns_av_unetI/netI     0.0304
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            5493
_diffrn_reflns_point_group_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.429
_diffrn_reflns_theta_min         2.410
_diffrn_ambient_temperature      170
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.978
_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         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2080
_reflns_number_total             2363
_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         0.214
_refine_diff_density_min         -0.350
_refine_diff_density_rms         0.076
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         2363
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0410
_refine_ls_R_factor_gt           0.0363
_refine_ls_restrained_S_all      1.085
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0677P)²+0.1009P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1031
_refine_ls_wR_factor_ref         0.1108
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All N(H,H) groups
 At 1.5 times of:
  All O(H) groups
2.a Rotating group:
 N12(H12A,H12B)
2.b Idealised tetrahedral OH refined as rotating group:
 O3(H3), O4(H4)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
_atom_sites_special_details      
;
The structure was solved using Direct Methods (ShelXS). RE = 0.2, Nqual =  -1, Ralpha = 0.036
;
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 0.06264(15) 0.59988(12) 0.31301(12) 0.0210(2) Uani 1 1 d . . . . .
O3 O 0.56958(15) 0.91984(13) 0.81313(14) 0.0249(3) Uani 1 1 d . . . . .
H3 H 0.5433 0.8153 0.7906 0.037 Uiso 1 1 calc GR . . . .
O1W O -0.15354(16) 0.24768(13) 0.10436(13) 0.0199(2) Uani 1 1 d . . . . .
O4 O 0.85892(15) 0.88609(13) 1.09714(13) 0.0242(3) Uani 1 1 d . . . . .
H4 H 0.7960 0.7916 1.0444 0.036 Uiso 1 1 calc GR . . . .
O2 O 0.25497(16) 0.83799(12) 0.43900(13) 0.0248(3) Uani 1 1 d . . . . .
N6 N 0.32396(16) 0.36578(14) 0.59761(14) 0.0148(3) Uani 1 1 d . . . . .
N7 N 0.54378(16) 0.59136(14) 0.79158(14) 0.0162(3) Uani 1 1 d . . . . .
N10 N 0.53836(16) 0.33069(14) 0.80954(14) 0.0164(3) Uani 1 1 d . . . . .
N2 N 0.28571(17) 0.61235(14) 0.52284(14) 0.0163(3) Uani 1 1 d . . . . .
N9 N 0.66968(17) 0.43765(14) 0.92611(14) 0.0170(3) Uani 1 1 d . . . . .
N8 N 0.67257(17) 0.59079(14) 0.91508(14) 0.0165(3) Uani 1 1 d . . . . .
N1 N 0.19682(17) 0.68020(14) 0.42139(14) 0.0164(3) Uani 1 1 d . . . . .
N11 N 0.41362(18) 0.96706(15) 0.75810(16) 0.0189(3) Uani 1 1 d . . . . .
N5 N 0.26085(18) 0.19691(15) 0.54487(15) 0.0200(3) Uani 1 1 d . . . . .
N12 N 1.03637(17) 0.88281(15) 1.16129(15) 0.0193(3) Uani 1 1 d . . . . .
H12A H 1.0276 0.7931 1.2014 0.023 Uiso 1 1 d GR . . . .
H12B H 1.0993 0.8844 1.0879 0.023 Uiso 1 1 d GR . . . .
N4 N 0.13860(18) 0.17466(15) 0.41930(15) 0.0209(3) Uani 1 1 d . . . . .
N3 N 0.11642(17) 0.32114(14) 0.38398(14) 0.0176(3) Uani 1 1 d . . . . .
C2 C 0.46601(18) 0.43010(16) 0.73171(15) 0.0132(3) Uani 1 1 d . . . . .
C1 C 0.23448(18) 0.44114(16) 0.49633(16) 0.0141(3) Uani 1 1 d . . . . .
H1WA H -0.199(3) 0.317(3) 0.070(3) 0.036(6) Uiso 1 1 d . . . . .
H1WB H -0.065(4) 0.295(3) 0.184(3) 0.044(6) Uiso 1 1 d . . . . .
H11A H 0.323(3) 0.924(2) 0.815(2) 0.029(5) Uiso 1 1 d . . . . .
H11B H 0.454(3) 1.079(3) 0.783(2) 0.030(5) Uiso 1 1 d . . . . .
H11C H 0.370(3) 0.934(3) 0.647(3) 0.039(6) Uiso 1 1 d . . . . .
H12C H 1.084(3) 0.974(3) 1.250(3) 0.042(6) 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
O1 N1 1.2502(16) . ?
O3 H3 0.8400 . ?
O3 N11 1.4137(16) . ?
O1W H1WA 0.83(2) . ?
O1W H1WB 0.86(3) . ?
O4 H4 0.8400 . ?
O4 N12 1.4114(16) . ?
O2 N1 1.2620(15) . ?
N6 N5 1.3659(15) . ?
N6 C2 1.4025(18) . ?
N6 C1 1.3634(18) . ?
N7 N8 1.3473(18) . ?
N7 C2 1.3255(17) . ?
N10 N9 1.3449(17) . ?
N10 C2 1.3300(18) . ?
N2 N1 1.3186(17) . ?
N2 C1 1.3683(17) . ?
N9 N8 1.3058(17) . ?
N11 H11A 0.93(2) . ?
N11 H11B 0.89(2) . ?
N11 H11C 0.95(2) . ?
N5 N4 1.2833(19) . ?
N12 H12A 0.8609 . ?
N12 H12B 0.8611 . ?
N12 H12C 0.96(2) . ?
N4 N3 1.3636(17) . ?
N3 C1 1.3308(18) . ?

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
N11 O3 H3 109.5 . . ?
H1WA O1W H1WB 111(2) . . ?
N12 O4 H4 109.5 . . ?
N5 N6 C2 118.86(11) . . ?
C1 N6 N5 108.73(11) . . ?
C1 N6 C2 132.31(11) . . ?
C2 N7 N8 103.08(11) . . ?
C2 N10 N9 103.74(11) . . ?
N1 N2 C1 116.11(12) . . ?
N8 N9 N10 109.29(12) . . ?
N9 N8 N7 110.43(11) . . ?
O1 N1 O2 119.56(12) . . ?
O1 N1 N2 124.79(11) . . ?
O2 N1 N2 115.65(12) . . ?
O3 N11 H11A 108.3(12) . . ?
O3 N11 H11B 103.7(14) . . ?
O3 N11 H11C 112.7(14) . . ?
H11A N11 H11B 109.7(17) . . ?
H11A N11 H11C 112.4(18) . . ?
H11B N11 H11C 109.6(19) . . ?
N4 N5 N6 105.51(11) . . ?
O4 N12 H12A 109.6 . . ?
O4 N12 H12B 109.7 . . ?
O4 N12 H12C 105.3(14) . . ?
H12A N12 H12B 109.4 . . ?
H12A N12 H12C 105.6 . . ?
H12B N12 H12C 117.1 . . ?
N5 N4 N3 112.57(11) . . ?
C1 N3 N4 105.70(12) . . ?
N7 C2 N6 124.87(12) . . ?
N7 C2 N10 113.46(13) . . ?
N10 C2 N6 121.66(12) . . ?
N6 C1 N2 118.06(12) . . ?
N3 C1 N6 107.48(12) . . ?
N3 C1 N2 134.36(13) . . ?

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
N6 N5 N4 N3 0.27(16) . . . . ?
N10 N9 N8 N7 0.10(15) . . . . ?
N9 N10 C2 N6 178.90(12) . . . . ?
N9 N10 C2 N7 0.23(15) . . . . ?
N8 N7 C2 N6 -178.80(12) . . . . ?
N8 N7 C2 N10 -0.17(15) . . . . ?
N1 N2 C1 N6 179.44(11) . . . . ?
N1 N2 C1 N3 3.5(2) . . . . ?
N5 N6 C2 N7 177.54(12) . . . . ?
N5 N6 C2 N10 -0.98(19) . . . . ?
N5 N6 C1 N2 -176.18(11) . . . . ?
N5 N6 C1 N3 0.76(15) . . . . ?
N5 N4 N3 C1 0.20(16) . . . . ?
N4 N3 C1 N6 -0.57(15) . . . . ?
N4 N3 C1 N2 175.65(14) . . . . ?
C2 N6 N5 N4 -177.50(12) . . . . ?
C2 N6 C1 N2 0.1(2) . . . . ?
C2 N6 C1 N3 177.06(13) . . . . ?
C2 N7 N8 N9 0.04(15) . . . . ?
C2 N10 N9 N8 -0.19(14) . . . . ?
C1 N6 N5 N4 -0.62(15) . . . . ?
C1 N6 C2 N7 1.5(2) . . . . ?
C1 N6 C2 N10 -176.98(13) . . . . ?
C1 N2 N1 O1 5.82(19) . . . . ?
C1 N2 N1 O2 -174.42(11) . . . . ?

_shelx_SHELXL_version_number     2014/7
_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_2017060_0m
_database_code_depnum_ccdc_archive 'CCDC 1534410'
_audit_update_record             
;
2017-02-23 deposited with the CCDC.
2017-09-12 downloaded from the CCDC.
;
_audit_creation_date             2017-02-16
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2017.01.04 svn.r3372 for OlexSys, GUI svn.r5292)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         '2(H2 O), C H6 N5 O2, C2 H N10 O2'
_chemical_formula_sum            'C3 H11 N15 O6'
_chemical_formula_weight         353.27
_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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.6274(11)
_cell_length_b                   9.3787(14)
_cell_length_c                   11.2469(18)
_cell_angle_alpha                102.272(3)
_cell_angle_beta                 91.229(3)
_cell_angle_gamma                105.997(3)
_cell_volume                     654.25(18)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1797
_cell_measurement_temperature    298
_cell_measurement_theta_max      27.79
_cell_measurement_theta_min      2.62
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.162
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6503
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2008/1 (Bruker,2008) was used for absorption correction. wR2(int) was 0.0526 before and 0.0392 after correction. The Ratio of minimum to maximum transmission is 0.8722. The λ/2 correction factor is 0.0015.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.793
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             364
_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  0.0215
_diffrn_reflns_av_unetI/netI     0.0389
_diffrn_reflns_Laue_measured_fraction_full 0.981
_diffrn_reflns_Laue_measured_fraction_max 0.961
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            5908
_diffrn_reflns_point_group_measured_fraction_full 0.981
_diffrn_reflns_point_group_measured_fraction_max 0.961
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.841
_diffrn_reflns_theta_min         1.860
_diffrn_ambient_temperature      298
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.961
_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         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2315
_reflns_number_total             2983
_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         0.505
_refine_diff_density_min         -0.403
_refine_diff_density_rms         0.118
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     261
_refine_ls_number_reflns         2983
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0790
_refine_ls_R_factor_gt           0.0641
_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)+(0.1346P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1742
_refine_ls_wR_factor_ref         0.1898
_refine_special_details          ?
_olex2_refinement_description    
;
;
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
_atom_sites_special_details      
;
The structure was solved using Direct Methods (ShelXS). RE = 0.2, Nqual =  -1, Ralpha = 0.069
;
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
O2W O 0.2157(3) 0.4926(2) 0.08702(18) 0.0380(5) Uani 1 1 d . . . . .
N14 N 0.3227(3) 0.2778(2) 0.88740(17) 0.0290(4) Uani 1 1 d . . . . .
O1W O 0.1392(3) 0.7629(2) 0.9345(2) 0.0398(5) Uani 1 1 d . . . . .
O4 O 0.1981(4) 0.0191(2) 0.82903(18) 0.0525(6) Uani 1 1 d . . . . .
O3 O 0.3406(4) 0.1308(2) 1.01142(17) 0.0501(6) Uani 1 1 d . . . . .
O2 O 0.2431(3) 0.3365(2) 0.46633(17) 0.0441(5) Uani 1 1 d . . . . .
O1 O 0.2881(3) 0.30288(19) 0.27309(16) 0.0387(5) Uani 1 1 d . . . . .
N15 N 0.2865(3) 0.1363(2) 0.90826(18) 0.0312(5) Uani 1 1 d . . . . .
N6 N 0.2525(3) 0.7653(2) 0.47646(17) 0.0258(4) Uani 1 1 d . . . . .
N2 N 0.2741(3) 0.5275(2) 0.36823(18) 0.0297(5) Uani 1 1 d . . . . .
N1 N 0.2684(3) 0.3870(2) 0.37239(18) 0.0279(4) Uani 1 1 d . . . . .
N7 N 0.2689(3) 0.9897(2) 0.40800(18) 0.0314(5) Uani 1 1 d . . . . .
N8 N 0.2617(3) 1.0131(2) 0.29572(19) 0.0308(5) Uani 1 1 d . . . . .
N11 N 0.3723(4) 0.5550(2) 0.87430(19) 0.0299(5) Uani 1 1 d . . . . .
N12 N 0.2905(3) 0.4361(2) 0.76849(19) 0.0299(5) Uani 1 1 d . . . . .
C3 C 0.2847(3) 0.2921(2) 0.7738(2) 0.0251(5) Uani 1 1 d . . . . .
N13 N 0.2434(3) 0.1888(2) 0.6695(2) 0.0311(5) Uani 1 1 d . . . . .
N9 N 0.2462(3) 0.8921(2) 0.20905(19) 0.0335(5) Uani 1 1 d . . . . .
N10 N 0.2411(3) 0.7792(2) 0.26432(18) 0.0311(5) Uani 1 1 d . . . . .
C2 C 0.2554(3) 0.8431(2) 0.3832(2) 0.0240(5) Uani 1 1 d . . . . .
C1 C 0.2586(3) 0.6202(2) 0.4763(2) 0.0249(5) Uani 1 1 d . . . . .
N5 N 0.2406(4) 0.8384(2) 0.59358(19) 0.0343(5) Uani 1 1 d . . . . .
N4 N 0.2390(4) 0.7421(2) 0.65972(19) 0.0383(5) Uani 1 1 d . . . . .
N3 N 0.2500(3) 0.6058(2) 0.59125(18) 0.0326(5) Uani 1 1 d . . . . .
H11A H 0.513(4) 0.578(3) 0.881(2) 0.029(7) Uiso 1 1 d . . . . .
H2WA H 0.115(5) 0.417(4) 0.084(3) 0.048(9) Uiso 1 1 d . . . . .
H11B H 0.324(5) 0.520(4) 0.941(3) 0.042(8) Uiso 1 1 d . . . . .
H13A H 0.247(6) 0.105(4) 0.668(3) 0.058(10) Uiso 1 1 d . . . . .
H12 H 0.276(5) 0.459(4) 0.694(3) 0.052(9) Uiso 1 1 d . . . . .
H13B H 0.232(5) 0.209(4) 0.591(3) 0.058(10) Uiso 1 1 d . . . . .
H1WA H 0.193(6) 0.813(5) 1.002(4) 0.076(14) Uiso 1 1 d . . . . .
H2WB H 0.212(5) 0.553(4) 0.153(3) 0.057(10) Uiso 1 1 d . . . . .
H11C H 0.306(6) 0.645(4) 0.874(3) 0.069(10) Uiso 1 1 d . . . . .
H1WB H 0.156(8) 0.833(6) 0.885(5) 0.114(18) Uiso 1 1 d . . . . .
H8 H 0.267(6) 1.114(5) 0.282(4) 0.074(11) 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
O2W H2WA 0.82(4) . ?
O2W H2WB 0.84(4) . ?
N14 N15 1.354(2) . ?
N14 C3 1.339(3) . ?
O1W H1WA 0.81(5) . ?
O1W H1WB 0.93(6) . ?
O4 N15 1.246(3) . ?
O3 N15 1.223(3) . ?
O2 N1 1.243(3) . ?
O1 N1 1.255(3) . ?
N6 C2 1.398(3) . ?
N6 C1 1.372(3) . ?
N6 N5 1.365(3) . ?
N2 N1 1.319(2) . ?
N2 C1 1.360(3) . ?
N7 N8 1.329(3) . ?
N7 C2 1.320(3) . ?
N8 N9 1.307(3) . ?
N8 H8 0.98(4) . ?
N11 N12 1.424(3) . ?
N11 H11A 0.90(3) . ?
N11 H11B 0.91(3) . ?
N11 H11C 1.05(4) . ?
N12 C3 1.354(3) . ?
N12 H12 0.92(4) . ?
C3 N13 1.321(3) . ?
N13 H13A 0.79(4) . ?
N13 H13B 0.95(4) . ?
N9 N10 1.331(3) . ?
N10 C2 1.333(3) . ?
C1 N3 1.329(3) . ?
N5 N4 1.285(3) . ?
N4 N3 1.366(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
H2WA O2W H2WB 106(3) . . ?
C3 N14 N15 118.79(19) . . ?
H1WA O1W H1WB 105(4) . . ?
O4 N15 N14 122.45(19) . . ?
O3 N15 N14 115.64(19) . . ?
O3 N15 O4 121.9(2) . . ?
C1 N6 C2 132.4(2) . . ?
N5 N6 C2 119.00(18) . . ?
N5 N6 C1 108.56(18) . . ?
N1 N2 C1 115.82(18) . . ?
O2 N1 O1 120.43(19) . . ?
O2 N1 N2 123.9(2) . . ?
O1 N1 N2 115.61(18) . . ?
C2 N7 N8 100.39(19) . . ?
N7 N8 H8 121(2) . . ?
N9 N8 N7 114.29(18) . . ?
N9 N8 H8 124(2) . . ?
N12 N11 H11A 109.1(17) . . ?
N12 N11 H11B 108(2) . . ?
N12 N11 H11C 110(2) . . ?
H11A N11 H11B 108(2) . . ?
H11A N11 H11C 117(3) . . ?
H11B N11 H11C 104(3) . . ?
N11 N12 H12 120(2) . . ?
C3 N12 N11 118.33(18) . . ?
C3 N12 H12 119(2) . . ?
N14 C3 N12 113.0(2) . . ?
N13 C3 N14 130.0(2) . . ?
N13 C3 N12 117.0(2) . . ?
C3 N13 H13A 120(3) . . ?
C3 N13 H13B 125(2) . . ?
H13A N13 H13B 114(3) . . ?
N8 N9 N10 106.36(19) . . ?
N9 N10 C2 104.58(18) . . ?
N7 C2 N6 121.0(2) . . ?
N7 C2 N10 114.4(2) . . ?
N10 C2 N6 124.57(19) . . ?
N2 C1 N6 118.39(19) . . ?
N3 C1 N6 106.97(19) . . ?
N3 C1 N2 134.6(2) . . ?
N4 N5 N6 106.21(19) . . ?
N5 N4 N3 111.7(2) . . ?
C1 N3 N4 106.60(19) . . ?

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
N15 N14 C3 N12 168.9(2) . . . . ?
N15 N14 C3 N13 -11.1(4) . . . . ?
N6 C1 N3 N4 0.0(2) . . . . ?
N6 N5 N4 N3 0.2(3) . . . . ?
N2 C1 N3 N4 178.9(3) . . . . ?
N1 N2 C1 N6 -176.65(18) . . . . ?
N1 N2 C1 N3 4.5(4) . . . . ?
N7 N8 N9 N10 0.4(3) . . . . ?
N8 N7 C2 N6 -178.67(19) . . . . ?
N8 N7 C2 N10 0.1(3) . . . . ?
N8 N9 N10 C2 -0.3(2) . . . . ?
N11 N12 C3 N14 11.6(3) . . . . ?
N11 N12 C3 N13 -168.5(2) . . . . ?
C3 N14 N15 O4 -7.9(3) . . . . ?
C3 N14 N15 O3 174.2(2) . . . . ?
N9 N10 C2 N6 178.8(2) . . . . ?
N9 N10 C2 N7 0.1(3) . . . . ?
C2 N6 C1 N2 1.3(4) . . . . ?
C2 N6 C1 N3 -179.6(2) . . . . ?
C2 N6 N5 N4 179.56(19) . . . . ?
C2 N7 N8 N9 -0.3(3) . . . . ?
C1 N6 C2 N7 -173.2(2) . . . . ?
C1 N6 C2 N10 8.1(4) . . . . ?
C1 N6 N5 N4 -0.2(3) . . . . ?
C1 N2 N1 O2 2.5(3) . . . . ?
C1 N2 N1 O1 -178.3(2) . . . . ?
N5 N6 C2 N7 7.1(3) . . . . ?
N5 N6 C2 N10 -171.5(2) . . . . ?
N5 N6 C1 N2 -178.96(19) . . . . ?
N5 N6 C1 N3 0.1(2) . . . . ?
N5 N4 N3 C1 -0.1(3) . . . . ?

_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_2016597_0m
_database_code_depnum_ccdc_archive 'CCDC 1534355'
_audit_update_record             
;
2017-04-13 deposited with the CCDC.
2017-09-12 downloaded from the CCDC.
;
_audit_creation_date             2017-04-13
_audit_creation_method           
;
Olex2 1.2-beta
(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         'C8 H8 K4 N36'
_chemical_formula_sum            'C8 H8 K4 N36'
_chemical_formula_weight         764.90
_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'

_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                   7.767(3)
_cell_length_b                   11.993(4)
_cell_length_c                   7.360(3)
_cell_angle_alpha                90
_cell_angle_beta                 101.904(14)
_cell_angle_gamma                90
_cell_volume                     670.8(4)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    3509
_cell_measurement_temperature    170
_cell_measurement_theta_max      27.012
_cell_measurement_theta_min      2.680
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.746
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6650
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2008/1 (Bruker,2008) was used for absorption correction. wR2(int) was 0.0600 before and 0.0487 after correction. The Ratio of minimum to maximum transmission is 0.8919. 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    1.893
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             384
_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  0.0301
_diffrn_reflns_av_unetI/netI     0.0241
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            8770
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.497
_diffrn_reflns_theta_min         2.680
_diffrn_ambient_temperature      170
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.981
_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         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1340
_reflns_number_total             1516
_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         0.251
_refine_diff_density_min         -0.245
_refine_diff_density_rms         0.053
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     117
_refine_ls_number_reflns         1516
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0308
_refine_ls_R_factor_gt           0.0259
_refine_ls_restrained_S_all      1.061
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0339P)²+0.1517P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0631
_refine_ls_wR_factor_ref         0.0657
_refine_special_details          ?
_olex2_refinement_description    
;
;
_atom_sites_solution_hydrogens   difmap
_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
K1 K 0.86409(4) 0.73879(2) 0.43818(4) 0.01940(11) Uani 1 1 d . . . . .
N5 N 0.68095(15) 0.37443(9) 0.84942(17) 0.0166(3) Uani 1 1 d . . . . .
N9 N 0.97543(16) 0.40264(10) 0.80418(18) 0.0186(3) Uani 1 1 d . . . . .
N8 N 1.05507(16) 0.49267(10) 0.74767(18) 0.0201(3) Uani 1 1 d . . . . .
N7 N 0.94497(16) 0.57584(10) 0.71334(18) 0.0199(3) Uani 1 1 d . . . . .
N6 N 0.78685(16) 0.54454(10) 0.74701(18) 0.0197(3) Uani 1 1 d . . . . .
N2 N 0.42871(16) 0.30713(10) 0.87937(19) 0.0219(3) Uani 1 1 d . . . . .
N4 N 0.71242(18) 0.26966(10) 0.9255(2) 0.0233(3) Uani 1 1 d . . . . .
N1 N 0.42969(18) 0.48914(11) 0.7493(2) 0.0265(3) Uani 1 1 d . . . . .
N3 N 0.56107(18) 0.23257(11) 0.9415(2) 0.0256(3) Uani 1 1 d . . . . .
C2 C 0.81358(18) 0.43940(11) 0.80094(19) 0.0150(3) Uani 1 1 d . . . . .
C1 C 0.50641(19) 0.39586(12) 0.8222(2) 0.0179(3) Uani 1 1 d . . . . .
H1A H 0.493(2) 0.5384(15) 0.713(2) 0.025(5) Uiso 1 1 d . . . . .
H1B H 0.310(3) 0.4971(15) 0.739(3) 0.031(5) 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
K1 K1 3.6898(16) 4_575 ?
K1 K1 3.6898(16) 4_576 ?
K1 N9 2.8348(15) 2_756 ?
K1 N9 2.9206(14) 3_766 ?
K1 N8 3.2133(15) 3_766 ?
K1 N7 2.7912(15) . ?
K1 N7 2.9163(14) 4_575 ?
K1 N6 2.9571(15) 4_575 ?
K1 N2 2.9571(16) 3_666 ?
K1 N2 2.9844(14) 2_656 ?
K1 N4 3.2560(18) 2_756 ?
K1 C1 3.5052(18) 3_666 ?
N5 N4 1.3767(17) . ?
N5 C2 1.3954(17) . ?
N5 C1 1.3536(19) . ?
N9 K1 2.8348(15) 2_746 ?
N9 K1 2.9206(14) 3_766 ?
N9 N8 1.3518(16) . ?
N9 C2 1.3277(18) . ?
N8 K1 3.2133(15) 3_766 ?
N8 N7 1.3042(17) . ?
N7 K1 2.9162(14) 4_576 ?
N7 N6 1.3550(17) . ?
N6 K1 2.9571(15) 4_576 ?
N6 C2 1.3254(19) . ?
N2 K1 2.9843(14) 2_646 ?
N2 K1 2.9571(16) 3_666 ?
N2 N3 1.3680(19) . ?
N2 C1 1.3334(18) . ?
N4 K1 3.2560(18) 2_746 ?
N4 N3 1.2849(19) . ?
N1 C1 1.328(2) . ?
N1 H1A 0.847(19) . ?
N1 H1B 0.918(19) . ?
C1 K1 3.5052(17) 3_666 ?

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 171.642(19) 4_575 4_576 ?
N9 K1 K1 121.75(3) 2_756 4_575 ?
N9 K1 K1 49.11(3) 3_766 4_575 ?
N9 K1 K1 51.16(3) 2_756 4_576 ?
N9 K1 K1 137.67(3) 3_766 4_576 ?
N9 K1 N9 128.83(5) 2_756 3_766 ?
N9 K1 N8 141.82(4) 2_756 3_766 ?
N9 K1 N8 24.88(3) 3_766 3_766 ?
N9 K1 N7 74.61(5) 2_756 4_575 ?
N9 K1 N6 74.17(4) 2_756 4_575 ?
N9 K1 N6 106.86(4) 3_766 4_575 ?
N9 K1 N2 144.90(4) 2_756 3_666 ?
N9 K1 N2 76.39(4) 3_766 3_666 ?
N9 K1 N2 77.25(4) 2_756 2_656 ?
N9 K1 N2 153.53(4) 3_766 2_656 ?
N9 K1 N4 55.82(3) 2_756 2_756 ?
N9 K1 N4 73.92(4) 3_766 2_756 ?
N9 K1 C1 152.04(3) 2_756 3_666 ?
N9 K1 C1 78.70(4) 3_766 3_666 ?
N8 K1 K1 121.85(3) 3_766 4_576 ?
N8 K1 K1 66.31(3) 3_766 4_575 ?
N8 K1 N4 87.47(3) 3_766 2_756 ?
N8 K1 C1 65.15(4) 3_766 3_666 ?
N7 K1 K1 48.26(3) 4_575 4_575 ?
N7 K1 K1 51.22(3) . 4_576 ?
N7 K1 K1 136.75(3) . 4_575 ?
N7 K1 K1 123.69(3) 4_575 4_576 ?
N7 K1 N9 88.62(4) . 3_766 ?
N7 K1 N9 85.82(4) 4_575 3_766 ?
N7 K1 N9 89.88(5) . 2_756 ?
N7 K1 N8 70.70(4) . 3_766 ?
N7 K1 N8 109.46(4) 4_575 3_766 ?
N7 K1 N7 154.54(5) . 4_575 ?
N7 K1 N6 162.51(4) . 4_575 ?
N7 K1 N6 26.67(3) 4_575 4_575 ?
N7 K1 N2 86.80(4) . 2_656 ?
N7 K1 N2 108.62(4) 4_575 2_656 ?
N7 K1 N2 117.67(4) . 3_666 ?
N7 K1 N2 85.07(4) 4_575 3_666 ?
N7 K1 N4 76.47(4) 4_575 2_756 ?
N7 K1 N4 78.12(4) . 2_756 ?
N7 K1 C1 96.36(4) . 3_666 ?
N7 K1 C1 106.83(4) 4_575 3_666 ?
N6 K1 K1 60.21(3) 4_575 4_575 ?
N6 K1 K1 111.64(3) 4_575 4_576 ?
N6 K1 N8 126.50(4) 4_575 3_766 ?
N6 K1 N2 74.94(4) 4_575 3_666 ?
N6 K1 N2 82.77(4) 4_575 2_656 ?
N6 K1 N4 98.02(4) 4_575 2_756 ?
N6 K1 C1 94.68(4) 4_575 3_666 ?
N2 K1 K1 51.94(3) 3_666 4_575 ?
N2 K1 K1 125.84(3) 2_656 4_575 ?
N2 K1 K1 51.28(3) 2_656 4_576 ?
N2 K1 K1 130.06(3) 3_666 4_576 ?
N2 K1 N8 131.51(3) 2_656 3_766 ?
N2 K1 N8 71.86(4) 3_666 3_766 ?
N2 K1 N2 82.74(5) 3_666 2_656 ?
N2 K1 N4 130.18(4) 2_656 2_756 ?
N2 K1 N4 145.90(4) 3_666 2_756 ?
N2 K1 C1 75.92(4) 2_656 3_666 ?
N2 K1 C1 21.76(3) 3_666 3_666 ?
N4 K1 K1 83.81(3) 2_756 4_576 ?
N4 K1 K1 95.24(3) 2_756 4_575 ?
N4 K1 C1 152.14(3) 2_756 3_666 ?
C1 K1 K1 114.21(3) 3_666 4_576 ?
C1 K1 K1 69.95(3) 3_666 4_575 ?
N4 N5 C2 122.35(12) . . ?
C1 N5 N4 108.77(11) . . ?
C1 N5 C2 128.74(12) . . ?
K1 N9 K1 79.73(4) 2_746 3_766 ?
N8 N9 K1 126.40(9) . 2_746 ?
N8 N9 K1 89.77(8) . 3_766 ?
C2 N9 K1 121.75(9) . 2_746 ?
C2 N9 K1 134.72(10) . 3_766 ?
C2 N9 N8 102.76(11) . . ?
N9 N8 K1 65.35(7) . 3_766 ?
N7 N8 K1 139.13(10) . 3_766 ?
N7 N8 N9 110.31(11) . . ?
K1 N7 K1 80.52(4) . 4_576 ?
N8 N7 K1 135.77(9) . . ?
N8 N7 K1 133.04(10) . 4_576 ?
N8 N7 N6 109.60(11) . . ?
N6 N7 K1 104.47(9) . . ?
N6 N7 K1 78.35(8) . 4_576 ?
N7 N6 K1 74.99(7) . 4_576 ?
C2 N6 K1 133.61(10) . 4_576 ?
C2 N6 N7 103.09(11) . . ?
K1 N2 K1 76.78(4) 3_666 2_646 ?
N3 N2 K1 105.07(9) . 2_646 ?
N3 N2 K1 123.00(9) . 3_666 ?
C1 N2 K1 102.93(10) . 3_666 ?
C1 N2 K1 142.89(9) . 2_646 ?
C1 N2 N3 105.62(12) . . ?
N5 N4 K1 108.21(8) . 2_746 ?
N3 N4 K1 144.84(10) . 2_746 ?
N3 N4 N5 105.32(12) . . ?
C1 N1 H1A 118.1(12) . . ?
C1 N1 H1B 118.9(11) . . ?
H1A N1 H1B 123.0(17) . . ?
N4 N3 N2 112.44(12) . . ?
N9 C2 N5 123.79(13) . . ?
N6 C2 N5 121.98(12) . . ?
N6 C2 N9 114.24(12) . . ?
N5 C1 K1 132.65(9) . 3_666 ?
N2 C1 K1 55.31(8) . 3_666 ?
N2 C1 N5 107.85(12) . . ?
N1 C1 K1 85.29(10) . 3_666 ?
N1 C1 N5 124.89(13) . . ?
N1 C1 N2 127.26(14) . . ?

_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_2016736-wbs4-298k_0ma
_database_code_depnum_ccdc_archive 'CCDC 1534406'
_audit_update_record             
;
2017-02-23 deposited with the CCDC.
2017-09-12 downloaded from the CCDC.
;
_audit_creation_date             2017-01-13
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2017.01.04 svn.r3372 for OlexSys, GUI svn.r5289)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C2 H N10 O2, H4 N, H2 O'
_chemical_formula_sum            'C2 H7 N11 O3'
_chemical_formula_weight         233.19
_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                   6.663(9)
_cell_length_b                   16.418(17)
_cell_length_c                   16.589(17)
_cell_angle_alpha                90
_cell_angle_beta                 99.96(3)
_cell_angle_gamma                90
_cell_volume                     1787(3)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    621
_cell_measurement_temperature    170
_cell_measurement_theta_max      23.73
_cell_measurement_theta_min      2.48
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.152
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.6293
_exptl_absorpt_correction_type   ?
_exptl_absorpt_process_details   
'SADABS-2008/1 (Bruker,2008) was used for absorption correction. wR2(int) was 0.0368 before and 0.0274 after correction. The Ratio of minimum to maximum transmission is 0.8441. 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    1.733
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             960
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.05
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0421
_diffrn_reflns_av_unetI/netI     0.0485
_diffrn_reflns_Laue_measured_fraction_full 0.970
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            9118
_diffrn_reflns_point_group_measured_fraction_full 0.970
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.346
_diffrn_reflns_theta_min         1.758
_diffrn_ambient_temperature      170
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.970
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '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         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2173
_reflns_number_total             3160
_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         0.313
_refine_diff_density_min         -0.490
_refine_diff_density_rms         0.099
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     325
_refine_ls_number_reflns         3160
_refine_ls_number_restraints     23
_refine_ls_R_factor_all          0.0809
_refine_ls_R_factor_gt           0.0545
_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)+(0.1249P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1613
_refine_ls_wR_factor_ref         0.1812
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.5 times of:
  All N(H,H) groups, All O(H,H) groups
2. Restrained distances
 N8-H8
 0.85 with sigma of 0.02
 H19-N19
 0.85 with sigma of 0.02
 N22-H22B = N22-H22D = N22-H22A = N22-H22C
 0.86 with sigma of 0.02
 H22B-H22D
 1.46 with sigma of 0.02
 N11-H11C = N11-H11A = N11-H11B
 0.86 with sigma of 0.02
 N11-H11D
 0.85 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(N11) \\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.01
Uanis(N11) \\sim Ueq, Uanis(N22) \\sim Ueq: with sigma of 0.005 and sigma for
terminal atoms of 0.01
4.a Free rotating group:
 N22(H22A,H22B), O1W(H1WA,H1WB), N11(H11A,H11B), O2W(H2WA,H2WB)
;
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
_atom_sites_special_details      
;
The structure was solved using Direct Methods (ShelXS). RE = 0.4, Nqual =  -1, Ralpha = 0.295
;
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
N17 N 0.9631(4) 0.33209(13) 0.74307(14) 0.0266(6) Uani 1 1 d . . . . .
N6 N 0.4307(4) 0.24295(14) 0.66767(13) 0.0286(6) Uani 1 1 d . . . . .
N22 N 0.9141(5) 0.37733(14) 1.00567(15) 0.0321(7) Uani 1 1 d D U . . .
H22A H 0.8117 0.4090 0.9991 0.048 Uiso 1 1 d DG . . . .
H22B H 0.9142 0.3500 0.9622 0.048 Uiso 1 1 d DG . . . .
N13 N 0.9478(4) 0.26503(14) 0.86627(14) 0.0305(6) Uani 1 1 d . . . . .
O3 O 0.9134(4) 0.19942(13) 0.97653(14) 0.0522(7) Uani 1 1 d . . . . .
O1 O 0.5160(4) 0.47937(13) 0.80714(14) 0.0520(7) Uani 1 1 d . . . . .
O2 O 0.4837(4) 0.37028(14) 0.87590(14) 0.0546(7) Uani 1 1 d . . . . .
N2 N 0.4748(4) 0.36691(14) 0.73819(14) 0.0315(6) Uani 1 1 d . . . . .
N3 N 0.4434(4) 0.23077(14) 0.79845(14) 0.0315(6) Uani 1 1 d . . . . .
O4 O 0.9139(5) 0.12810(13) 0.86800(15) 0.0596(8) Uani 1 1 d . . . . .
N19 N 1.0287(4) 0.53457(14) 0.76854(16) 0.0351(7) Uani 1 1 d D . . . .
N14 N 0.9261(4) 0.20207(14) 0.73039(15) 0.0315(6) Uani 1 1 d . . . . .
N16 N 0.9523(4) 0.31445(14) 0.66171(15) 0.0332(6) Uani 1 1 d . . . . .
N1 N 0.4921(4) 0.40484(15) 0.80983(14) 0.0329(6) Uani 1 1 d . . . . .
N5 N 0.4129(4) 0.16246(15) 0.68315(16) 0.0357(7) Uani 1 1 d . . . . .
N8 N 0.4278(4) 0.26915(16) 0.46531(15) 0.0358(7) Uani 1 1 d D . . . .
N12 N 0.9242(4) 0.19430(14) 0.90313(16) 0.0354(7) Uani 1 1 d . . . . .
N15 N 0.9300(4) 0.23726(15) 0.65629(15) 0.0363(7) Uani 1 1 d . . . . .
N4 N 0.4215(4) 0.15674(15) 0.76050(16) 0.0376(7) Uani 1 1 d . . . . .
N7 N 0.4419(4) 0.21877(15) 0.52752(15) 0.0392(7) Uani 1 1 d . . . . .
O1W O 0.6983(4) 0.53209(16) 0.97284(17) 0.0589(8) Uani 1 1 d . . . . .
H1WA H 0.6182 0.5283 0.9272 0.088 Uiso 1 1 d G . . . .
H1WB H 0.6538 0.5681 1.0022 0.088 Uiso 1 1 d G . . . .
N18 N 1.0056(5) 0.47244(14) 0.71780(16) 0.0408(7) Uani 1 1 d . . . . .
N11 N 0.4763(6) 0.51109(17) 0.62536(17) 0.0455(8) Uani 1 1 d D U . . .
H11A H 0.5048 0.5453 0.6642 0.068 Uiso 1 1 d DG . . . .
H11B H 0.3704 0.5266 0.5929 0.068 Uiso 1 1 d DG . . . .
N10 N 0.4046(5) 0.34611(16) 0.56387(16) 0.0486(8) Uani 1 1 d . . . . .
N9 N 0.4080(5) 0.34461(16) 0.48390(16) 0.0471(8) Uani 1 1 d . . . . .
C3 C 0.9462(4) 0.26165(16) 0.78498(17) 0.0249(6) Uani 1 1 d . . . . .
C1 C 0.4506(4) 0.28522(17) 0.73974(16) 0.0247(6) Uani 1 1 d . . . . .
N21 N 1.0007(5) 0.43597(15) 0.84599(17) 0.0519(9) Uani 1 1 d . . . . .
O2W O 0.8190(5) 0.03409(18) 1.02924(19) 0.0726(9) Uani 1 1 d . . . . .
H2WA H 0.8879 0.0060 1.0673 0.109 Uiso 1 1 d G . . . .
H2WB H 0.8654 0.0824 1.0311 0.109 Uiso 1 1 d G . . . .
C2 C 0.4253(5) 0.26942(17) 0.58723(17) 0.0285(7) Uani 1 1 d . . . . .
C4 C 0.9883(4) 0.41295(16) 0.76912(17) 0.0276(7) Uani 1 1 d . . . . .
N20 N 1.0254(5) 0.51587(16) 0.84351(17) 0.0498(8) Uani 1 1 d . . . . .
H19 H 1.050(5) 0.5832(14) 0.756(2) 0.055(11) Uiso 1 1 d D . . . .
H8 H 0.433(5) 0.253(2) 0.4162(14) 0.054(11) Uiso 1 1 d D . . . .
H22C H 1.026(4) 0.398(2) 1.023(3) 0.060(13) Uiso 1 1 d D . . . .
H22D H 0.887(10) 0.350(3) 1.046(2) 0.14(3) Uiso 1 1 d D . . . .
H11C H 0.460(10) 0.466(2) 0.650(4) 0.14(2) Uiso 1 1 d D . . . .
H11D H 0.561(8) 0.491(4) 0.600(4) 0.13(3) Uiso 1 1 d D . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N17 N16 1.370(4) . ?
N17 C3 1.364(4) . ?
N17 C4 1.397(4) . ?
N6 N5 1.355(4) . ?
N6 C1 1.369(4) . ?
N6 C2 1.398(4) . ?
N22 H22A 0.8503 . ?
N22 H22B 0.8496 . ?
N22 H22C 0.825(19) . ?
N22 H22D 0.852(19) . ?
N13 N12 1.334(3) . ?
N13 C3 1.348(4) . ?
O3 N12 1.235(4) . ?
O1 N1 1.236(3) . ?
O2 N1 1.244(3) . ?
N2 N1 1.329(4) . ?
N2 C1 1.352(4) . ?
N3 N4 1.365(4) . ?
N3 C1 1.329(4) . ?
O4 N12 1.229(3) . ?
N19 N18 1.315(4) . ?
N19 N20 1.285(4) . ?
N19 H19 0.841(19) . ?
N14 N15 1.363(4) . ?
N14 C3 1.324(4) . ?
N16 N15 1.277(4) . ?
N5 N4 1.278(4) . ?
N8 N7 1.313(4) . ?
N8 N9 1.289(4) . ?
N8 H8 0.865(19) . ?
N7 C2 1.313(4) . ?
O1W H1WA 0.8493 . ?
O1W H1WB 0.8512 . ?
N18 C4 1.314(4) . ?
N11 H11A 0.8504 . ?
N11 H11B 0.8500 . ?
N11 H11C 0.86(2) . ?
N11 H11D 0.83(2) . ?
N10 N9 1.331(4) . ?
N10 C2 1.318(4) . ?
N21 C4 1.319(4) . ?
N21 N20 1.324(4) . ?
O2W H2WA 0.8503 . ?
O2W H2WB 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
N16 N17 C4 119.2(2) . . ?
C3 N17 N16 109.1(2) . . ?
C3 N17 C4 131.6(3) . . ?
N5 N6 C1 109.1(2) . . ?
N5 N6 C2 119.7(2) . . ?
C1 N6 C2 131.2(3) . . ?
H22A N22 H22B 109.5 . . ?
H22A N22 H22C 116.3 . . ?
H22A N22 H22D 98.4 . . ?
H22B N22 H22C 112.9 . . ?
H22B N22 H22D 114.8 . . ?
H22C N22 H22D 104(5) . . ?
N12 N13 C3 116.2(2) . . ?
N1 N2 C1 116.1(2) . . ?
C1 N3 N4 106.0(2) . . ?
N18 N19 H19 126(3) . . ?
N20 N19 N18 114.5(2) . . ?
N20 N19 H19 120(3) . . ?
C3 N14 N15 106.8(2) . . ?
N15 N16 N17 105.3(2) . . ?
O1 N1 O2 120.6(3) . . ?
O1 N1 N2 115.1(2) . . ?
O2 N1 N2 124.3(3) . . ?
N4 N5 N6 105.8(2) . . ?
N7 N8 H8 122(3) . . ?
N9 N8 N7 114.4(3) . . ?
N9 N8 H8 123(3) . . ?
O3 N12 N13 115.1(2) . . ?
O4 N12 N13 123.6(3) . . ?
O4 N12 O3 121.3(3) . . ?
N16 N15 N14 112.2(2) . . ?
N5 N4 N3 112.3(2) . . ?
C2 N7 N8 101.0(3) . . ?
H1WA O1W H1WB 109.4 . . ?
C4 N18 N19 100.1(3) . . ?
H11A N11 H11B 109.5 . . ?
H11A N11 H11C 103.4 . . ?
H11A N11 H11D 124.3 . . ?
H11B N11 H11C 113.6 . . ?
H11B N11 H11D 111.0 . . ?
H11C N11 H11D 94(6) . . ?
C2 N10 N9 104.9(3) . . ?
N8 N9 N10 106.0(3) . . ?
N13 C3 N17 119.2(2) . . ?
N14 C3 N17 106.6(3) . . ?
N14 C3 N13 134.2(3) . . ?
N2 C1 N6 118.7(2) . . ?
N3 C1 N6 106.8(2) . . ?
N3 C1 N2 134.5(3) . . ?
C4 N21 N20 104.0(3) . . ?
H2WA O2W H2WB 109.5 . . ?
N7 C2 N6 122.1(3) . . ?
N7 C2 N10 113.7(3) . . ?
N10 C2 N6 124.2(3) . . ?
N18 C4 N17 121.7(3) . . ?
N18 C4 N21 114.6(3) . . ?
N21 C4 N17 123.7(3) . . ?
N19 N20 N21 106.9(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
N17 N16 N15 N14 -0.2(3) . . . . ?
N6 N5 N4 N3 0.4(3) . . . . ?
N19 N18 C4 N17 -179.1(3) . . . . ?
N19 N18 C4 N21 -0.3(4) . . . . ?
N16 N17 C3 N13 -178.4(2) . . . . ?
N16 N17 C3 N14 0.2(3) . . . . ?
N16 N17 C4 N18 -1.2(4) . . . . ?
N16 N17 C4 N21 -179.9(3) . . . . ?
N1 N2 C1 N6 179.6(3) . . . . ?
N1 N2 C1 N3 -1.7(5) . . . . ?
N5 N6 C1 N2 178.6(2) . . . . ?
N5 N6 C1 N3 -0.4(3) . . . . ?
N5 N6 C2 N7 -13.1(4) . . . . ?
N5 N6 C2 N10 167.3(3) . . . . ?
N8 N7 C2 N6 179.7(3) . . . . ?
N8 N7 C2 N10 -0.7(4) . . . . ?
N12 N13 C3 N17 177.9(2) . . . . ?
N12 N13 C3 N14 -0.1(5) . . . . ?
N15 N14 C3 N17 -0.3(3) . . . . ?
N15 N14 C3 N13 177.9(3) . . . . ?
N4 N3 C1 N6 0.6(3) . . . . ?
N4 N3 C1 N2 -178.2(3) . . . . ?
N7 N8 N9 N10 -1.2(4) . . . . ?
N18 N19 N20 N21 0.6(4) . . . . ?
N9 N8 N7 C2 1.1(4) . . . . ?
N9 N10 C2 N6 179.7(3) . . . . ?
N9 N10 C2 N7 0.0(4) . . . . ?
C3 N17 N16 N15 0.0(3) . . . . ?
C3 N17 C4 N18 178.6(3) . . . . ?
C3 N17 C4 N21 -0.1(5) . . . . ?
C3 N13 N12 O3 -175.7(3) . . . . ?
C3 N13 N12 O4 4.4(4) . . . . ?
C3 N14 N15 N16 0.3(3) . . . . ?
C1 N6 N5 N4 0.1(3) . . . . ?
C1 N6 C2 N7 167.5(3) . . . . ?
C1 N6 C2 N10 -12.2(5) . . . . ?
C1 N2 N1 O1 179.3(3) . . . . ?
C1 N2 N1 O2 -1.3(4) . . . . ?
C1 N3 N4 N5 -0.6(3) . . . . ?
C2 N6 N5 N4 -179.5(3) . . . . ?
C2 N6 C1 N2 -1.9(5) . . . . ?
C2 N6 C1 N3 179.1(3) . . . . ?
C2 N10 N9 N8 0.7(4) . . . . ?
C4 N17 N16 N15 179.9(2) . . . . ?
C4 N17 C3 N13 1.8(5) . . . . ?
C4 N17 C3 N14 -179.6(3) . . . . ?
C4 N21 N20 N19 -0.7(4) . . . . ?
N20 N19 N18 C4 -0.2(4) . . . . ?
N20 N21 C4 N17 179.4(3) . . . . ?
N20 N21 C4 N18 0.7(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
