# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_c103
_database_code_depnum_ccdc_archive 'CCDC 2087553'
_audit_update_record             
;
2021-06-02 deposited with the CCDC.	2022-02-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H6 N14 O16'
_chemical_formula_weight         626.33

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

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   5.843(3)
_cell_length_b                   7.177(3)
_cell_length_c                   14.405(6)
_cell_angle_alpha                87.865(6)
_cell_angle_beta                 88.438(6)
_cell_angle_gamma                80.502(6)
_cell_volume                     595.2(4)
_cell_formula_units_Z            1
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1996
_cell_measurement_theta_min      2.83
_cell_measurement_theta_max      27.33

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.747
_exptl_crystal_F_000             316
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.090
_exptl_absorpt_coefficient_mu    0.161
_shelx_estimated_absorpt_T_min   0.981
_shelx_estimated_absorpt_T_max   0.986
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            3668
_diffrn_reflns_av_unetI/netI     0.0353
_diffrn_reflns_av_R_equivalents  0.0160
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.415
_diffrn_reflns_theta_max         27.456
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measured_fraction_theta_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_point_group_measured_fraction_full 0.987
_reflns_number_total             2632
_reflns_number_gt                2188
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1200P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2632
_refine_ls_number_parameters     200
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0514
_refine_ls_R_factor_gt           0.0438
_refine_ls_wR_factor_ref         0.1661
_refine_ls_wR_factor_gt          0.1529
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_restrained_S_all      1.081
_refine_ls_shift/su_max          0.013
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.8220(2) 0.47888(19) 0.86753(9) 0.0489(4) Uani 1 1 d . . . . .
O2 O 0.4502(3) 0.4435(2) 0.89367(11) 0.0612(4) Uani 1 1 d . . . . .
O3 O 0.6558(4) 0.8528(3) 0.92337(11) 0.0754(5) Uani 1 1 d . U . . .
O4 O 0.6622(3) 0.9974(2) 0.78954(12) 0.0694(5) Uani 1 1 d . . . . .
O5 O 0.1845(3) 0.8560(2) 0.85554(10) 0.0667(5) Uani 1 1 d . . . . .
O6 O 0.1786(2) 0.6808(2) 0.73806(11) 0.0577(4) Uani 1 1 d . . . . .
O7 O 0.7459(2) 0.50364(15) 0.67972(8) 0.0396(3) Uani 1 1 d . . . . .
O8 O 0.7156(3) 0.7478(2) 0.31435(9) 0.0567(4) Uani 1 1 d . . . . .
N2 N 0.6264(3) 0.8721(2) 0.84125(10) 0.0423(4) Uani 1 1 d . U . . .
N3 N 0.2733(3) 0.7533(2) 0.79616(10) 0.0420(4) Uani 1 1 d . . . . .
N4 N 0.6033(2) 0.79089(19) 0.62788(10) 0.0397(4) Uani 1 1 d . . . . .
N5 N 0.8034(3) 0.5114(2) 0.58497(10) 0.0415(4) Uani 1 1 d . . . . .
N6 N 0.6518(3) 0.6633(2) 0.39588(11) 0.0507(4) Uani 1 1 d . . . . .
N7 N 0.8429(3) 0.8854(2) 0.33008(10) 0.0472(4) Uani 1 1 d . . . . .
N8 N 0.9877(3) 1.01368(19) 0.45705(9) 0.0407(4) Uani 1 1 d . . . . .
C1 C 0.9117(4) 0.3077(3) 0.92165(16) 0.0576(5) Uani 1 1 d . . . . .
H1A H 1.076732 0.277762 0.912122 0.086 Uiso 1 1 calc R U . . .
H1B H 0.840343 0.204888 0.902046 0.086 Uiso 1 1 calc R U . . .
H1C H 0.877027 0.327886 0.986383 0.086 Uiso 1 1 calc R U . . .
C2 C 0.5976(3) 0.5216(2) 0.86031(11) 0.0397(4) Uani 1 1 d . . . . .
C3 C 0.5402(3) 0.7021(2) 0.79645(11) 0.0360(4) Uani 1 1 d . . . . .
C4 C 0.6292(3) 0.6742(2) 0.69828(11) 0.0327(3) Uani 1 1 d . . . . .
C5 C 0.7161(3) 0.6818(2) 0.55922(11) 0.0334(4) Uani 1 1 d . . . . .
C6 C 0.7389(3) 0.7463(2) 0.46194(11) 0.0356(4) Uani 1 1 d . . . . .
C7 C 0.8602(3) 0.8861(2) 0.41997(11) 0.0368(4) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C2 1.302(2) . ?
O1 C1 1.459(2) . ?
O2 C2 1.185(2) . ?
O3 N2 1.200(2) . ?
O4 N2 1.188(2) . ?
O5 N3 1.200(2) . ?
O6 N3 1.196(2) . ?
O7 C4 1.3316(19) . ?
O7 N5 1.3981(19) . ?
O8 N7 1.360(2) . ?
O8 N6 1.372(2) . ?
N2 C3 1.561(2) . ?
N3 C3 1.542(2) . ?
N4 C4 1.287(2) . ?
N4 C5 1.370(2) . ?
N5 C5 1.290(2) . ?
N6 C6 1.299(2) . ?
N7 C7 1.302(2) . ?
N8 N8 1.254(3) 2_776 ?
N8 C7 1.401(2) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 C3 1.556(2) . ?
C3 C4 1.502(2) . ?
C5 C6 1.469(2) . ?
C6 C7 1.428(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
C2 O1 C1 117.18(15) . . ?
C4 O7 N5 105.53(12) . . ?
N7 O8 N6 111.56(13) . . ?
O4 N2 O3 129.27(17) . . ?
O4 N2 C3 116.23(15) . . ?
O3 N2 C3 114.42(15) . . ?
O6 N3 O5 127.58(17) . . ?
O6 N3 C3 115.71(14) . . ?
O5 N3 C3 116.67(15) . . ?
C4 N4 C5 101.21(13) . . ?
C5 N5 O7 103.42(12) . . ?
C6 N6 O8 105.96(15) . . ?
C7 N7 O8 105.22(15) . . ?
N8 N8 C7 111.77(17) 2_776 . ?
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O2 C2 O1 129.36(16) . . ?
O2 C2 C3 121.82(16) . . ?
O1 C2 C3 108.82(14) . . ?
C4 C3 N3 109.00(12) . . ?
C4 C3 C2 113.37(13) . . ?
N3 C3 C2 106.36(13) . . ?
C4 C3 N2 112.21(13) . . ?
N3 C3 N2 105.47(12) . . ?
C2 C3 N2 109.94(13) . . ?
N4 C4 O7 114.55(14) . . ?
N4 C4 C3 129.10(14) . . ?
O7 C4 C3 116.32(13) . . ?
N5 C5 N4 115.29(14) . . ?
N5 C5 C6 120.21(14) . . ?
N4 C5 C6 124.50(14) . . ?
N6 C6 C7 107.86(15) . . ?
N6 C6 C5 120.51(16) . . ?
C7 C6 C5 131.48(15) . . ?
N7 C7 N8 118.11(15) . . ?
N7 C7 C6 109.39(16) . . ?
N8 C7 C6 132.49(15) . . ?

_refine_diff_density_max         0.343
_refine_diff_density_min         -0.306
_refine_diff_density_rms         0.052

####################################################################### 
# 
# 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_C102
_database_code_depnum_ccdc_archive 'CCDC 2087555'
_audit_update_record             
;
2021-06-02 deposited with the CCDC.	2022-02-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C H0.80 N1.60 O1.40'
_chemical_formula_weight         57.63

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

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

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

_cell_length_a                   11.796(3)
_cell_length_b                   7.4634(18)
_cell_length_c                   11.526(3)
_cell_angle_alpha                90
_cell_angle_beta                 96.659(4)
_cell_angle_gamma                90
_cell_volume                     1007.9(4)
_cell_formula_units_Z            20
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1442
_cell_measurement_theta_min      3.24
_cell_measurement_theta_max      23.94

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.899
_exptl_crystal_F_000             584
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.10
_exptl_absorpt_coefficient_mu    0.176
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6023
_diffrn_reflns_av_unetI/netI     0.0459
_diffrn_reflns_av_R_equivalents  0.0383
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         1.738
_diffrn_reflns_theta_max         27.495
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2309
_reflns_number_gt                1532
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2309
_refine_ls_number_parameters     184
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0740
_refine_ls_R_factor_gt           0.0463
_refine_ls_wR_factor_ref         0.1603
_refine_ls_wR_factor_gt          0.1347
_refine_ls_goodness_of_fit_ref   0.965
_refine_ls_restrained_S_all      0.965
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.001

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.03592(16) 1.2957(2) 0.19418(15) 0.0597(5) Uani 1 1 d . . . . .
H1 H 0.069(2) 1.261(3) 0.134(2) 0.090 Uiso 1 1 calc R U . . .
O2 O 0.21666(17) 0.9695(2) 0.44491(17) 0.0644(5) Uani 1 1 d . . . . .
O3 O 0.09926(19) 0.9079(2) 0.5644(2) 0.0794(7) Uani 1 1 d . . . . .
O4 O 0.10879(16) 0.5927(2) 0.64114(13) 0.0574(5) Uani 1 1 d . . . . .
O5 O 0.13735(14) 0.3890(2) 0.51560(13) 0.0508(5) Uani 1 1 d . . . . .
O6 O 0.30361(16) 0.7455(2) 0.32652(14) 0.0567(5) Uani 1 1 d . . . . .
O7 O 0.38902(15) 0.0818(2) 0.11942(16) 0.0620(5) Uani 1 1 d . . . . .
N1 N 0.07963(16) 1.1981(2) 0.29224(15) 0.0431(5) Uani 1 1 d . . . . .
H1A H 0.099490 1.089171 0.270435 0.065 Uiso 1 1 calc R U . . .
H1B H 0.026720 1.188654 0.341033 0.065 Uiso 1 1 calc R U . . .
H1C H 0.140618 1.253936 0.327937 0.065 Uiso 1 1 calc R U . . .
N2 N 0.47547(19) 0.5101(3) 0.04223(18) 0.0533(6) Uani 1 1 d . . . . .
N3 N 0.44452(18) 0.1908(3) 0.04856(19) 0.0551(6) Uani 1 1 d . . . . .
N4 N 0.33998(19) 0.1797(3) 0.20186(18) 0.0529(5) Uani 1 1 d . . . . .
N5 N 0.3572(2) 0.6550(3) 0.24108(19) 0.0601(6) Uani 1 1 d . . . . .
N6 N 0.25674(15) 0.4613(2) 0.33827(15) 0.0400(4) Uani 1 1 d . . . . .
N7 N 0.16621(16) 0.8591(2) 0.49793(16) 0.0419(5) Uani 1 1 d . . . . .
N8 N 0.14056(14) 0.5492(2) 0.54636(14) 0.0379(4) Uani 1 1 d . . . . .
C2 C 0.18436(18) 0.6761(3) 0.47566(18) 0.0368(5) Uani 1 1 d . . . . .
C4 C 0.24621(17) 0.6214(3) 0.38097(17) 0.0364(5) Uani 1 1 d . . . . .
C5 C 0.32727(18) 0.4893(3) 0.25387(18) 0.0397(5) Uani 1 1 d . . . . .
C6 C 0.36552(18) 0.3456(3) 0.18336(18) 0.0413(5) Uani 1 1 d . . . . .
C7 C 0.43130(19) 0.3519(3) 0.08748(18) 0.0425(5) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 N1 1.393(2) . ?
O1 H1 0.87(3) . ?
O2 N7 1.221(2) . ?
O3 N7 1.218(2) . ?
O4 N8 1.239(2) . ?
O5 N8 1.246(2) . ?
O6 C4 1.345(2) . ?
O6 N5 1.404(2) . ?
O7 N3 1.372(2) . ?
O7 N4 1.378(2) . ?
N1 H1A 0.8900 . ?
N1 H1B 0.8900 . ?
N1 H1C 0.8900 . ?
N2 N2 1.198(4) 3_665 ?
N2 C7 1.415(3) . ?
N3 C7 1.299(3) . ?
N4 C6 1.298(3) . ?
N5 C5 1.299(3) . ?
N6 C4 1.304(3) . ?
N6 C5 1.368(2) . ?
N7 C2 1.410(3) . ?
N8 C2 1.388(2) . ?
C2 C4 1.441(3) . ?
C5 C6 1.449(3) . ?
C6 C7 1.423(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
N1 O1 H1 109.5 . . ?
C4 O6 N5 106.71(15) . . ?
N3 O7 N4 111.35(17) . . ?
O1 N1 H1A 109.5 . . ?
O1 N1 H1B 109.5 . . ?
H1A N1 H1B 109.5 . . ?
O1 N1 H1C 109.5 . . ?
H1A N1 H1C 109.5 . . ?
H1B N1 H1C 109.5 . . ?
N2 N2 C7 115.3(2) 3_665 . ?
C7 N3 O7 104.98(16) . . ?
C6 N4 O7 105.56(18) . . ?
C5 N5 O6 103.18(16) . . ?
C4 N6 C5 102.75(16) . . ?
O3 N7 O2 120.14(18) . . ?
O3 N7 C2 121.82(18) . . ?
O2 N7 C2 117.98(17) . . ?
O4 N8 O5 120.02(17) . . ?
O4 N8 C2 120.66(18) . . ?
O5 N8 C2 119.27(16) . . ?
N8 C2 N7 118.65(17) . . ?
N8 C2 C4 120.46(17) . . ?
N7 C2 C4 120.89(17) . . ?
N6 C4 O6 112.34(16) . . ?
N6 C4 C2 128.66(17) . . ?
O6 C4 C2 118.99(18) . . ?
N5 C5 N6 114.99(19) . . ?
N5 C5 C6 122.32(19) . . ?
N6 C5 C6 122.69(18) . . ?
N4 C6 C7 108.50(19) . . ?
N4 C6 C5 121.40(19) . . ?
C7 C6 C5 130.10(19) . . ?
N3 C7 N2 125.53(18) . . ?
N3 C7 C6 109.60(18) . . ?
N2 C7 C6 124.87(18) . . ?

_refine_diff_density_max         0.225
_refine_diff_density_min         -0.216
_refine_diff_density_rms         0.049

####################################################################### 
# 
# 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_P21_b
_database_code_depnum_ccdc_archive 'CCDC 2094944'
loop_
_audit_author_name
_audit_author_address
'Chunlin He'
;Beijing Institute of Technology
China
;
_audit_update_record             
;
2022-01-29 deposited with the CCDC.	2022-02-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C28 H50 N36 O29'
_chemical_formula_weight         1355.04

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

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

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

_cell_length_a                   3.6502(5)
_cell_length_b                   17.024(3)
_cell_length_c                   41.865(6)
_cell_angle_alpha                90
_cell_angle_beta                 92.467(4)
_cell_angle_gamma                90
_cell_volume                     2599.1(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    170(2)
_cell_measurement_reflns_used    955
_cell_measurement_theta_min      2.393
_cell_measurement_theta_max      21.291

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.731
_exptl_crystal_F_000             1404
_exptl_transmission_factor_min   0.864
_exptl_transmission_factor_max   0.864
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.154
_shelx_estimated_absorpt_T_min   0.970
_shelx_estimated_absorpt_T_max   0.970
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      170(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ccd
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15885
_diffrn_reflns_av_unetI/netI     0.1728
_diffrn_reflns_av_R_equivalents  0.1504
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -49
_diffrn_reflns_limit_l_max       47
_diffrn_reflns_theta_min         1.196
_diffrn_reflns_theta_max         24.988
_diffrn_reflns_theta_full        24.988
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4650
_reflns_number_gt                2216
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
 Refined as a 2-component twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1458P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4650
_refine_ls_number_parameters     409
_refine_ls_number_restraints     16
_refine_ls_R_factor_all          0.2090
_refine_ls_R_factor_gt           0.0969
_refine_ls_wR_factor_ref         0.2758
_refine_ls_wR_factor_gt          0.2272
_refine_ls_goodness_of_fit_ref   0.973
_refine_ls_restrained_S_all      0.978
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_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 0.758(2) 0.2962(5) 0.70881(18) 0.073(2) Uani 1 1 d D U . . .
H1 H 0.6587 0.2820 0.7256 0.109 Uiso 1 1 calc R U . . .
C1 C 1.159(6) 0.4455(9) 0.7020(4) 0.165(7) Uani 1 1 d D U . . .
H1A H 1.2768 0.4735 0.7201 0.247 Uiso 1 1 d DR U . . .
H1B H 0.9879 0.4808 0.6904 0.247 Uiso 1 1 d R U . . .
H1C H 1.3460 0.4274 0.6876 0.247 Uiso 1 1 d DR U . . .
C2 C 0.942(5) 0.3738(8) 0.7142(4) 0.143(6) Uani 1 1 d D U . . .
H2A H 1.1056 0.3594 0.7328 0.171 Uiso 1 1 calc R U . . .
H2B H 0.7376 0.4022 0.7239 0.171 Uiso 1 1 calc R U . . .
N15_1 O 0.8332(18) 0.5896(3) 0.64330(14) 0.0411(16) Uani 1 1 d . . . . .
C15_1 O 0.1533(17) 0.8452(4) 0.70258(14) 0.0409(16) Uani 1 1 d . . . . .
O4_1 O 0.942(2) 0.7594(4) 0.57783(15) 0.058(2) Uani 1 1 d . . . . .
O5_1 O -0.1511(18) 0.4875(4) 0.77785(13) 0.0389(16) Uani 1 1 d . . . . .
O6_1 O 0.874(3) 0.5000(5) 0.5957(2) 0.104(4) Uani 1 1 d . . . . .
O7_1 O 1.148(3) 0.6810(4) 0.54364(16) 0.072(3) Uani 1 1 d . . . . .
O8_1 O 0.4050(17) 0.7040(3) 0.87080(13) 0.0361(15) Uani 1 1 d . . . . .
O9_1 O 1.159(3) 0.5391(4) 0.5556(2) 0.078(3) Uani 1 1 d . . . . .
O10_1 O 0.035(2) 0.7704(4) 0.91955(14) 0.0456(17) Uani 1 1 d . . . . .
O11_1 O 0.275(3) 0.5743(4) 0.96693(14) 0.071(3) Uani 1 1 d . . . . .
O12_1 O 0.246(2) 0.7285(4) 0.96553(15) 0.058(2) Uani 1 1 d . . . . .
O13_1 O 0.488(2) 0.5233(4) 0.92408(15) 0.0464(17) Uani 1 1 d . . . . .
N1_1 N 0.684(2) 0.6205(5) 0.67143(17) 0.043(2) Uani 1 1 d . . . . .
N2_1 N 0.6475(19) 0.7088(4) 0.63164(15) 0.0296(17) Uani 1 1 d . . . . .
N3_1 N 0.306(2) 0.8123(5) 0.67660(16) 0.0370(19) Uani 1 1 d . . . . .
N4_1 N 0.162(2) 0.7908(5) 0.72843(16) 0.0366(19) Uani 1 1 d . . . . .
N5_1 N 1.014(2) 0.6913(5) 0.56943(17) 0.0377(19) Uani 1 1 d . . . . .
N6_1 N 0.393(2) 0.6629(4) 0.73424(14) 0.0330(18) Uani 1 1 d . . . . .
H6_1 H 0.4880 0.6216 0.7250 0.040 Uiso 1 1 d R U . . .
N7_1 N 0.312(2) 0.6638(4) 0.76677(15) 0.0354(19) Uani 1 1 d . . . . .
H7_1 H 0.3769 0.7018 0.7800 0.042 Uiso 1 1 d R U . . .
N8_1 N -0.102(2) 0.5109(5) 0.80944(16) 0.0365(19) Uani 1 1 d . . . . .
N9_1 N 0.000(2) 0.5437(5) 0.75715(17) 0.0364(19) Uani 1 1 d . . . . .
N10_1 N 1.018(2) 0.5528(4) 0.57966(17) 0.042(2) Uani 1 1 d . . . . .
N11_1 N 0.351(2) 0.6858(4) 0.83765(15) 0.0349(19) Uani 1 1 d . . . . .
N12_1 N 0.1111(19) 0.5900(4) 0.86801(16) 0.0291(17) Uani 1 1 d . . . . .
N13_1 N 0.185(2) 0.7176(5) 0.93652(18) 0.039(2) Uani 1 1 d . . . . .
N14_1 N 0.349(2) 0.5803(4) 0.93835(17) 0.037(2) Uani 1 1 d . . . . .
C3_1 C 0.588(2) 0.6892(6) 0.66273(19) 0.033(2) Uani 1 1 d . . . . .
C4_1 C 0.801(2) 0.6460(5) 0.62088(18) 0.029(2) Uani 1 1 d . . . . .
C5_1 C 0.415(2) 0.7417(5) 0.68475(18) 0.027(2) Uani 1 1 d . . . . .
C6_1 C 0.328(2) 0.7293(5) 0.71756(19) 0.0249(19) Uani 1 1 d . . . . .
C7_1 C 0.943(2) 0.6311(5) 0.58977(19) 0.031(2) Uani 1 1 d . . . . .
C8_1 C 0.140(2) 0.5990(5) 0.77645(18) 0.030(2) Uani 1 1 d . . . . .
C9_1 C 0.078(2) 0.5762(5) 0.80860(19) 0.028(2) Uani 1 1 d . . . . .
C10_1 C 0.177(2) 0.6196(5) 0.83803(17) 0.028(2) Uani 1 1 d . . . . .
C11_1 C 0.257(2) 0.6444(5) 0.8868(2) 0.030(2) Uani 1 1 d . . . . .
C12_1 C 0.269(2) 0.6473(5) 0.92128(18) 0.030(2) Uani 1 1 d . . . . .
N15_5 N 0.7104(19) 0.9182(4) 0.62512(15) 0.0324(18) Uani 1 1 d . . . . .
H15A_5 H 0.6618 0.9702 0.6221 0.039 Uiso 1 1 d R U . . .
H15B_5 H 0.6966 0.9061 0.6462 0.039 Uiso 1 1 d R U . . .
N14_5 N 0.4402(18) 0.8742(4) 0.60684(16) 0.0332(18) Uani 1 1 d . . . . .
H14A_5 H 0.5336 0.8258 0.6029 0.040 Uiso 1 1 d R U . . .
H14B_5 H 0.3940 0.8998 0.5880 0.040 Uiso 1 1 d R U . . .
H14C_5 H 0.2273 0.8689 0.6173 0.040 Uiso 1 1 d R U . . .
N15_9 O 0.540(2) 0.9035(5) 0.54032(17) 0.073(2) Uani 1 1 d . . . . .
H_9 H 0.5424 0.9446 0.5293 0.110 Uiso 1 1 d R U . . .
N14_9 C 0.320(4) 0.8484(6) 0.5205(2) 0.061(3) Uani 1 1 d . . . . .
HA_9 H 0.3731 0.7945 0.5275 0.091 Uiso 1 1 calc R U . . .
HB_9 H 0.3809 0.8544 0.4981 0.091 Uiso 1 1 calc R U . . .
HC_9 H 0.0588 0.8596 0.5228 0.091 Uiso 1 1 calc R U . . .
N15_3 N 0.554(2) 0.5791(5) 0.49552(17) 0.045(2) Uani 1 1 d . . . . .
H15A_3 H 0.4351 0.5659 0.5126 0.054 Uiso 1 1 d R U . . .
H15B_3 H 0.7023 0.6186 0.5003 0.054 Uiso 1 1 d R U . . .
N14_3 N 0.297(2) 0.6068(4) 0.47141(18) 0.041(2) Uani 1 1 d . . . . .
H14A_3 H 0.4037 0.6039 0.4522 0.061 Uiso 1 1 d R U . . .
H14B_3 H 0.1075 0.5720 0.4717 0.061 Uiso 1 1 d R U . . .
H14C_3 H 0.2100 0.6563 0.4744 0.061 Uiso 1 1 d R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C2 1.494(14) . ?
O1 H1 0.8400 . ?
C1 C2 1.554(16) . ?
C1 H1A 0.9802 . ?
C1 H1B 0.9799 . ?
C1 H1C 0.9799 . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
N15_1 C4_1 1.345(9) . ?
N15_1 N1_1 1.420(9) . ?
C15_1 N3_1 1.365(9) . ?
C15_1 N4_1 1.424(9) . ?
O4_1 N5_1 1.242(9) . ?
O5_1 N8_1 1.385(8) . ?
O5_1 N9_1 1.418(9) . ?
O6_1 N10_1 1.251(10) . ?
O7_1 N5_1 1.218(8) . ?
O8_1 C11_1 1.341(10) . ?
O8_1 N11_1 1.427(8) . ?
O9_1 N10_1 1.174(9) . ?
O10_1 N13_1 1.257(9) . ?
O11_1 N14_1 1.242(9) . ?
O12_1 N13_1 1.239(9) . ?
O13_1 N14_1 1.260(9) . ?
N1_1 C3_1 1.270(11) . ?
N2_1 C4_1 1.297(10) . ?
N2_1 C3_1 1.369(10) . ?
N3_1 C5_1 1.307(11) . ?
N4_1 C6_1 1.304(11) . ?
N5_1 C7_1 1.365(11) . ?
N6_1 C6_1 1.343(10) . ?
N6_1 N7_1 1.406(9) . ?
N6_1 H6_1 0.8808 . ?
N7_1 C8_1 1.340(11) . ?
N7_1 H7_1 0.8789 . ?
N8_1 C9_1 1.292(11) . ?
N9_1 C8_1 1.329(11) . ?
N10_1 C7_1 1.429(11) . ?
N11_1 C10_1 1.296(11) . ?
N12_1 C11_1 1.314(11) . ?
N12_1 C10_1 1.383(10) . ?
N13_1 C12_1 1.396(11) . ?
N14_1 C12_1 1.370(11) . ?
C3_1 C5_1 1.448(12) . ?
C4_1 C7_1 1.445(11) . ?
C5_1 C6_1 1.439(11) . ?
C8_1 C9_1 1.429(11) . ?
C9_1 C10_1 1.468(12) . ?
C11_1 C12_1 1.443(11) . ?
N15_5 N14_5 1.434(9) . ?
N15_5 H15A_5 0.9090 . ?
N15_5 H15B_5 0.9087 . ?
N14_5 H14A_5 0.9095 . ?
N14_5 H14B_5 0.9097 . ?
N14_5 H14C_5 0.9118 . ?
N15_9 N14_9 1.467(13) . ?
N15_9 H_9 0.8400 . ?
N14_9 HA_9 0.9800 . ?
N14_9 HB_9 0.9800 . ?
N14_9 HC_9 0.9800 . ?
N15_3 N14_3 1.429(10) . ?
N15_3 H15A_3 0.8801 . ?
N15_3 H15B_3 0.8803 . ?
N14_3 H14A_3 0.9099 . ?
N14_3 H14B_3 0.9100 . ?
N14_3 H14C_3 0.9101 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 O1 H1 109.5 . . ?
C2 C1 H1A 109.9 . . ?
C2 C1 H1B 108.9 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.6 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O1 C2 C1 151.1(13) . . ?
O1 C2 H2A 98.8 . . ?
C1 C2 H2A 98.8 . . ?
O1 C2 H2B 98.8 . . ?
C1 C2 H2B 98.8 . . ?
H2A C2 H2B 103.9 . . ?
C4_1 N15_1 N1_1 106.8(6) . . ?
N3_1 C15_1 N4_1 110.0(6) . . ?
N8_1 O5_1 N9_1 110.6(6) . . ?
C11_1 O8_1 N11_1 106.3(6) . . ?
C3_1 N1_1 N15_1 102.4(7) . . ?
C4_1 N2_1 C3_1 102.6(7) . . ?
C5_1 N3_1 C15_1 107.5(6) . . ?
C6_1 N4_1 C15_1 104.7(6) . . ?
O7_1 N5_1 O4_1 118.9(8) . . ?
O7_1 N5_1 C7_1 122.6(8) . . ?
O4_1 N5_1 C7_1 118.4(7) . . ?
C6_1 N6_1 N7_1 117.0(7) . . ?
C6_1 N6_1 H6_1 120.5 . . ?
N7_1 N6_1 H6_1 122.5 . . ?
C8_1 N7_1 N6_1 113.8(7) . . ?
C8_1 N7_1 H7_1 122.2 . . ?
N6_1 N7_1 H7_1 123.9 . . ?
C9_1 N8_1 O5_1 105.4(7) . . ?
C8_1 N9_1 O5_1 104.8(6) . . ?
O9_1 N10_1 O6_1 122.0(8) . . ?
O9_1 N10_1 C7_1 122.4(8) . . ?
O6_1 N10_1 C7_1 114.8(8) . . ?
C10_1 N11_1 O8_1 102.9(6) . . ?
C11_1 N12_1 C10_1 101.8(7) . . ?
O12_1 N13_1 O10_1 120.1(8) . . ?
O12_1 N13_1 C12_1 122.9(8) . . ?
O10_1 N13_1 C12_1 117.0(7) . . ?
O11_1 N14_1 O13_1 120.1(7) . . ?
O11_1 N14_1 C12_1 121.4(7) . . ?
O13_1 N14_1 C12_1 118.4(7) . . ?
N1_1 C3_1 N2_1 116.4(8) . . ?
N1_1 C3_1 C5_1 120.5(7) . . ?
N2_1 C3_1 C5_1 123.1(8) . . ?
N2_1 C4_1 N15_1 111.9(7) . . ?
N2_1 C4_1 C7_1 129.4(8) . . ?
N15_1 C4_1 C7_1 118.6(8) . . ?
N3_1 C5_1 C6_1 107.9(7) . . ?
N3_1 C5_1 C3_1 122.5(7) . . ?
C6_1 C5_1 C3_1 129.6(8) . . ?
N4_1 C6_1 N6_1 124.6(7) . . ?
N4_1 C6_1 C5_1 109.9(7) . . ?
N6_1 C6_1 C5_1 125.4(8) . . ?
N5_1 C7_1 N10_1 118.2(7) . . ?
N5_1 C7_1 C4_1 121.0(8) . . ?
N10_1 C7_1 C4_1 120.8(8) . . ?
N9_1 C8_1 N7_1 124.9(7) . . ?
N9_1 C8_1 C9_1 107.9(8) . . ?
N7_1 C8_1 C9_1 127.2(9) . . ?
N8_1 C9_1 C8_1 111.2(8) . . ?
N8_1 C9_1 C10_1 121.1(7) . . ?
C8_1 C9_1 C10_1 127.6(8) . . ?
N11_1 C10_1 N12_1 115.6(7) . . ?
N11_1 C10_1 C9_1 122.1(7) . . ?
N12_1 C10_1 C9_1 122.2(8) . . ?
N12_1 C11_1 O8_1 113.3(7) . . ?
N12_1 C11_1 C12_1 128.0(8) . . ?
O8_1 C11_1 C12_1 118.6(8) . . ?
N14_1 C12_1 N13_1 121.4(7) . . ?
N14_1 C12_1 C11_1 119.3(7) . . ?
N13_1 C12_1 C11_1 119.3(8) . . ?
N14_5 N15_5 H15A_5 108.0 . . ?
N14_5 N15_5 H15B_5 109.5 . . ?
H15A_5 N15_5 H15B_5 109.7 . . ?
N15_5 N14_5 H14A_5 108.4 . . ?
N15_5 N14_5 H14B_5 108.0 . . ?
H14A_5 N14_5 H14B_5 109.5 . . ?
N15_5 N14_5 H14C_5 112.1 . . ?
H14A_5 N14_5 H14C_5 109.4 . . ?
H14B_5 N14_5 H14C_5 109.4 . . ?
N14_9 N15_9 H_9 103.9 . . ?
N15_9 N14_9 HA_9 109.5 . . ?
N15_9 N14_9 HB_9 109.5 . . ?
HA_9 N14_9 HB_9 109.5 . . ?
N15_9 N14_9 HC_9 109.5 . . ?
HA_9 N14_9 HC_9 109.5 . . ?
HB_9 N14_9 HC_9 109.5 . . ?
N14_3 N15_3 H15A_3 108.9 . . ?
N14_3 N15_3 H15B_3 106.6 . . ?
H15A_3 N15_3 H15B_3 109.4 . . ?
N15_3 N14_3 H14A_3 108.1 . . ?
N15_3 N14_3 H14B_3 104.5 . . ?
H14A_3 N14_3 H14B_3 109.5 . . ?
N15_3 N14_3 H14C_3 115.6 . . ?
H14A_3 N14_3 H14C_3 109.5 . . ?
H14B_3 N14_3 H14C_3 109.5 . . ?

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
C4_1 N15_1 N1_1 C3_1 -0.6(9) . . . . ?
N4_1 C15_1 N3_1 C5_1 -1.2(9) . . . . ?
N3_1 C15_1 N4_1 C6_1 2.2(9) . . . . ?
C6_1 N6_1 N7_1 C8_1 136.7(8) . . . . ?
N9_1 O5_1 N8_1 C9_1 -1.8(9) . . . . ?
N8_1 O5_1 N9_1 C8_1 0.7(9) . . . . ?
C11_1 O8_1 N11_1 C10_1 0.9(8) . . . . ?
N15_1 N1_1 C3_1 N2_1 1.2(10) . . . . ?
N15_1 N1_1 C3_1 C5_1 179.2(8) . . . . ?
C4_1 N2_1 C3_1 N1_1 -1.3(11) . . . . ?
C4_1 N2_1 C3_1 C5_1 -179.2(8) . . . . ?
C3_1 N2_1 C4_1 N15_1 0.8(10) . . . . ?
C3_1 N2_1 C4_1 C7_1 -177.2(9) . . . . ?
N1_1 N15_1 C4_1 N2_1 -0.2(10) . . . . ?
N1_1 N15_1 C4_1 C7_1 178.1(7) . . . . ?
C15_1 N3_1 C5_1 C6_1 -0.2(9) . . . . ?
C15_1 N3_1 C5_1 C3_1 179.4(8) . . . . ?
N1_1 C3_1 C5_1 N3_1 -178.7(9) . . . . ?
N2_1 C3_1 C5_1 N3_1 -0.8(14) . . . . ?
N1_1 C3_1 C5_1 C6_1 0.8(15) . . . . ?
N2_1 C3_1 C5_1 C6_1 178.6(8) . . . . ?
C15_1 N4_1 C6_1 N6_1 -179.3(8) . . . . ?
C15_1 N4_1 C6_1 C5_1 -2.2(9) . . . . ?
N7_1 N6_1 C6_1 N4_1 -7.7(12) . . . . ?
N7_1 N6_1 C6_1 C5_1 175.7(8) . . . . ?
N3_1 C5_1 C6_1 N4_1 1.6(10) . . . . ?
C3_1 C5_1 C6_1 N4_1 -177.9(9) . . . . ?
N3_1 C5_1 C6_1 N6_1 178.7(8) . . . . ?
C3_1 C5_1 C6_1 N6_1 -0.9(15) . . . . ?
O7_1 N5_1 C7_1 N10_1 -2.3(14) . . . . ?
O4_1 N5_1 C7_1 N10_1 178.6(9) . . . . ?
O7_1 N5_1 C7_1 C4_1 176.7(9) . . . . ?
O4_1 N5_1 C7_1 C4_1 -2.4(13) . . . . ?
O9_1 N10_1 C7_1 N5_1 5.0(14) . . . . ?
O6_1 N10_1 C7_1 N5_1 -164.7(10) . . . . ?
O9_1 N10_1 C7_1 C4_1 -174.0(10) . . . . ?
O6_1 N10_1 C7_1 C4_1 16.3(14) . . . . ?
N2_1 C4_1 C7_1 N5_1 16.7(15) . . . . ?
N15_1 C4_1 C7_1 N5_1 -161.1(8) . . . . ?
N2_1 C4_1 C7_1 N10_1 -164.3(9) . . . . ?
N15_1 C4_1 C7_1 N10_1 17.9(13) . . . . ?
O5_1 N9_1 C8_1 N7_1 180.0(8) . . . . ?
O5_1 N9_1 C8_1 C9_1 0.6(9) . . . . ?
N6_1 N7_1 C8_1 N9_1 -10.8(12) . . . . ?
N6_1 N7_1 C8_1 C9_1 168.4(8) . . . . ?
O5_1 N8_1 C9_1 C8_1 2.1(9) . . . . ?
O5_1 N8_1 C9_1 C10_1 179.1(7) . . . . ?
N9_1 C8_1 C9_1 N8_1 -1.8(10) . . . . ?
N7_1 C8_1 C9_1 N8_1 178.8(8) . . . . ?
N9_1 C8_1 C9_1 C10_1 -178.5(8) . . . . ?
N7_1 C8_1 C9_1 C10_1 2.1(14) . . . . ?
O8_1 N11_1 C10_1 N12_1 -1.0(9) . . . . ?
O8_1 N11_1 C10_1 C9_1 -176.9(7) . . . . ?
C11_1 N12_1 C10_1 N11_1 0.7(10) . . . . ?
C11_1 N12_1 C10_1 C9_1 176.6(8) . . . . ?
N8_1 C9_1 C10_1 N11_1 -178.8(8) . . . . ?
C8_1 C9_1 C10_1 N11_1 -2.3(13) . . . . ?
N8_1 C9_1 C10_1 N12_1 5.6(12) . . . . ?
C8_1 C9_1 C10_1 N12_1 -178.0(8) . . . . ?
C10_1 N12_1 C11_1 O8_1 -0.1(9) . . . . ?
C10_1 N12_1 C11_1 C12_1 178.7(9) . . . . ?
N11_1 O8_1 C11_1 N12_1 -0.5(9) . . . . ?
N11_1 O8_1 C11_1 C12_1 -179.5(7) . . . . ?
O11_1 N14_1 C12_1 N13_1 15.6(14) . . . . ?
O13_1 N14_1 C12_1 N13_1 -166.8(8) . . . . ?
O11_1 N14_1 C12_1 C11_1 -162.0(10) . . . . ?
O13_1 N14_1 C12_1 C11_1 15.6(13) . . . . ?
O12_1 N13_1 C12_1 N14_1 14.5(14) . . . . ?
O10_1 N13_1 C12_1 N14_1 -164.0(8) . . . . ?
O12_1 N13_1 C12_1 C11_1 -167.9(9) . . . . ?
O10_1 N13_1 C12_1 C11_1 13.6(13) . . . . ?
N12_1 C11_1 C12_1 N14_1 42.6(14) . . . . ?
O8_1 C11_1 C12_1 N14_1 -138.6(8) . . . . ?
N12_1 C11_1 C12_1 N13_1 -135.0(9) . . . . ?
O8_1 C11_1 C12_1 N13_1 43.8(12) . . . . ?

_refine_diff_density_max         0.553
_refine_diff_density_min         -0.626
_refine_diff_density_rms         0.134



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

data_a_tw
_database_code_depnum_ccdc_archive 'CCDC 2087557'
_audit_update_record             
;
2021-06-02 deposited with the CCDC.	2022-02-01 downloaded from the CCDC.
;
_audit_creation_date             2019-04-24
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C5 H2 N7 O6, H2 O, H4 N'
_chemical_formula_sum            'C5 H8 N8 O7'
_chemical_formula_weight         292.19
_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                   13.575(3)
_cell_length_b                   11.854(2)
_cell_length_c                   6.6963(13)
_cell_angle_alpha                90
_cell_angle_beta                 98.79(3)
_cell_angle_gamma                90
_cell_volume                     1064.9(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3199
_cell_measurement_temperature    163(2)
_cell_measurement_theta_max      27.4816
_cell_measurement_theta_min      1.5179
_shelx_estimated_absorpt_T_max   0.997
_shelx_estimated_absorpt_T_min   0.979
_exptl_absorpt_coefficient_mu    0.168
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.7461
_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    1.823
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_av_unetI/netI     0.0788
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            2399
_diffrn_reflns_point_group_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.479
_diffrn_reflns_theta_min         1.518
_diffrn_ambient_temperature      163.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.980
_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                1947
_reflns_number_total             2399
_reflns_special_details          
;
 _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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.360
_refine_diff_density_min         -0.418
_refine_diff_density_rms         0.098
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.144
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         2399
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1085
_refine_ls_R_factor_gt           0.0884
_refine_ls_restrained_S_all      1.144
_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)+(0.0298P)²+2.9639P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1737
_refine_ls_wR_factor_ref         0.1851
_refine_special_details          
;
 Refined as a 2-component twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.794(7)
 0.206(7)
2. Fixed Uiso
 At 1.2 times of:
  All N(H,H) groups, All N(H,H,H,H) groups, All O(H,H) groups
3.a Riding coordinates:
 N7(H7A,H7B), O7(H7C,H7D), N8(H8A,H8B,H8C,H8D)
;
_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 0.7390(2) 0.4043(2) 0.2363(5) 0.0226(7) Uani 1 1 d . . . . .
O4 O 0.9320(2) 0.4034(2) 0.3692(5) 0.0309(8) Uani 1 1 d . . . . .
O2 O 0.7799(2) 0.0683(2) 0.2151(6) 0.0336(8) Uani 1 1 d . . . . .
O6 O 0.3617(2) 0.2454(2) 0.3676(5) 0.0269(7) Uani 1 1 d . . . . .
O5 O 0.9365(2) 0.0778(3) 0.3360(6) 0.0352(8) Uani 1 1 d . . . . .
N3 N 0.6679(2) 0.2454(3) 0.3177(5) 0.0177(7) Uani 1 1 d . . . . .
N1 N 0.8556(2) 0.1236(3) 0.2766(5) 0.0204(7) Uani 1 1 d . . . . .
N6 N 0.3385(2) 0.3608(3) 0.3330(6) 0.0234(8) Uani 1 1 d . . . . .
O3 O 1.0085(2) 0.2699(3) 0.2353(5) 0.0305(8) Uani 1 1 d . . . . .
N2 N 0.9340(2) 0.3083(3) 0.2940(5) 0.0202(7) Uani 1 1 d . . . . .
C4 C 0.4980(3) 0.3224(3) 0.3194(6) 0.0177(8) Uani 1 1 d . . . . .
N4 N 0.6388(2) 0.4307(3) 0.2488(6) 0.0221(8) Uani 1 1 d . . . . .
N7 N 0.4338(3) 0.5179(3) 0.2643(6) 0.0257(8) Uani 1 1 d . . . . .
H7A H 0.483814 0.543888 0.216732 0.031 Uiso 1 1 d R . . . .
H7B H 0.387964 0.563798 0.217232 0.031 Uiso 1 1 d R . . . .
N5 N 0.4597(2) 0.2257(3) 0.3577(6) 0.0230(8) Uani 1 1 d . . . . .
C2 C 0.7499(3) 0.2935(3) 0.2809(6) 0.0157(8) Uani 1 1 d . . . . .
C5 C 0.4221(3) 0.4081(3) 0.3015(6) 0.0184(8) Uani 1 1 d . . . . .
C1 C 0.8461(3) 0.2422(3) 0.2790(6) 0.0172(8) Uani 1 1 d . . . . .
C3 C 0.6025(3) 0.3339(3) 0.2944(6) 0.0181(8) Uani 1 1 d . . . . .
O7 O 0.1599(2) 0.3677(3) 0.9873(5) 0.0287(7) Uani 1 1 d . . . . .
H7C H 0.101591 0.392888 0.980695 0.034 Uiso 1 1 d R . . . .
H7D H 0.190482 0.404098 1.085335 0.034 Uiso 1 1 d R . . . .
N8 N 0.1575(3) 0.3753(3) 0.5617(6) 0.0286(9) Uani 1 1 d . . . . .
H8A H 0.148978 0.307190 0.523099 0.034 Uiso 1 1 d R . . . .
H8B H 0.175888 0.381040 0.688449 0.034 Uiso 1 1 d R . . . .
H8C H 0.112568 0.419910 0.505899 0.034 Uiso 1 1 d R . . . .
H8D H 0.208078 0.406900 0.525219 0.034 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 N4 1.411(4) . ?
O1 C2 1.350(4) . ?
O4 N2 1.237(4) . ?
O2 N1 1.235(4) . ?
O6 N6 1.415(4) . ?
O6 N5 1.363(4) . ?
O5 N1 1.236(4) . ?
N3 C2 1.306(5) . ?
N3 C3 1.369(5) . ?
N1 C1 1.412(5) . ?
N6 C5 1.311(5) . ?
O3 N2 1.228(4) . ?
N2 C1 1.418(5) . ?
C4 N5 1.301(5) . ?
C4 C5 1.440(5) . ?
C4 C3 1.460(5) . ?
N4 C3 1.303(5) . ?
N7 H7A 0.8500 . ?
N7 H7B 0.8501 . ?
N7 C5 1.339(5) . ?
C2 C1 1.443(5) . ?
O7 H7C 0.8400 . ?
O7 H7D 0.8402 . ?
N8 H8A 0.8499 . ?
N8 H8B 0.8501 . ?
N8 H8C 0.8500 . ?
N8 H8D 0.8498 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 O1 N4 106.0(3) . . ?
N5 O6 N6 110.6(3) . . ?
C2 N3 C3 101.5(3) . . ?
O2 N1 O5 121.9(3) . . ?
O2 N1 C1 117.4(3) . . ?
O5 N1 C1 120.8(3) . . ?
C5 N6 O6 105.3(3) . . ?
O4 N2 C1 117.6(3) . . ?
O3 N2 O4 122.6(3) . . ?
O3 N2 C1 119.8(3) . . ?
N5 C4 C5 109.6(3) . . ?
N5 C4 C3 122.0(4) . . ?
C5 C4 C3 128.3(3) . . ?
C3 N4 O1 102.8(3) . . ?
H7A N7 H7B 102.2 . . ?
C5 N7 H7A 123.1 . . ?
C5 N7 H7B 126.1 . . ?
C4 N5 O6 106.3(3) . . ?
O1 C2 C1 118.4(3) . . ?
N3 C2 O1 113.5(3) . . ?
N3 C2 C1 128.0(3) . . ?
N6 C5 C4 108.1(3) . . ?
N6 C5 N7 125.2(4) . . ?
N7 C5 C4 126.7(4) . . ?
N1 C1 N2 118.3(3) . . ?
N1 C1 C2 120.2(3) . . ?
N2 C1 C2 121.3(3) . . ?
N3 C3 C4 122.7(3) . . ?
N4 C3 N3 116.1(3) . . ?
N4 C3 C4 121.2(3) . . ?
H7C O7 H7D 102.1 . . ?
H8A N8 H8B 112.7 . . ?
H8A N8 H8C 113.7 . . ?
H8A N8 H8D 114.2 . . ?
H8B N8 H8C 118.0 . . ?
H8B N8 H8D 97.2 . . ?
H8C N8 H8D 99.0 . . ?

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 N4 C3 N3 1.2(5) . . . . ?
O1 N4 C3 C4 -179.1(3) . . . . ?
O1 C2 C1 N1 -164.9(4) . . . . ?
O1 C2 C1 N2 19.7(6) . . . . ?
O4 N2 C1 N1 -153.8(4) . . . . ?
O4 N2 C1 C2 21.7(6) . . . . ?
O2 N1 C1 N2 -162.8(4) . . . . ?
O2 N1 C1 C2 21.7(6) . . . . ?
O6 N6 C5 C4 -0.8(4) . . . . ?
O6 N6 C5 N7 -179.3(4) . . . . ?
O5 N1 C1 N2 17.9(6) . . . . ?
O5 N1 C1 C2 -157.7(4) . . . . ?
N3 C2 C1 N1 13.7(7) . . . . ?
N3 C2 C1 N2 -161.7(4) . . . . ?
N6 O6 N5 C4 0.1(5) . . . . ?
O3 N2 C1 N1 25.4(6) . . . . ?
O3 N2 C1 C2 -159.1(4) . . . . ?
N4 O1 C2 N3 0.9(4) . . . . ?
N4 O1 C2 C1 179.7(3) . . . . ?
N5 O6 N6 C5 0.5(4) . . . . ?
N5 C4 C5 N6 1.0(5) . . . . ?
N5 C4 C5 N7 179.4(4) . . . . ?
N5 C4 C3 N3 -2.8(6) . . . . ?
N5 C4 C3 N4 177.5(4) . . . . ?
C2 O1 N4 C3 -1.2(4) . . . . ?
C2 N3 C3 C4 179.6(4) . . . . ?
C2 N3 C3 N4 -0.6(5) . . . . ?
C5 C4 N5 O6 -0.6(5) . . . . ?
C5 C4 C3 N3 179.3(4) . . . . ?
C5 C4 C3 N4 -0.5(7) . . . . ?
C3 N3 C2 O1 -0.2(4) . . . . ?
C3 N3 C2 C1 -178.9(4) . . . . ?
C3 C4 N5 O6 -178.9(4) . . . . ?
C3 C4 C5 N6 179.1(4) . . . . ?
C3 C4 C5 N7 -2.4(7) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.794(7)
2 0.206(7)

####################################################################### 
# 
# 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_bwn18490
_database_code_depnum_ccdc_archive 'CCDC 2087554'
_audit_update_record             
;
2021-06-02 deposited with the CCDC.	2022-02-01 downloaded from the CCDC.
;
_audit_creation_date             2019-01-03
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C10 N14 O12, 2(H4 N), 2(H2 O)'
_chemical_formula_sum            'C10 H12 N16 O14'
_chemical_formula_weight         580.36
_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                   5.0442(10)
_cell_length_b                   13.949(3)
_cell_length_c                   15.122(3)
_cell_angle_alpha                90
_cell_angle_beta                 92.06(3)
_cell_angle_gamma                90
_cell_volume                     1063.4(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3624
_cell_measurement_temperature    153(2)
_cell_measurement_theta_max      27.4816
_cell_measurement_theta_min      1.4598
_shelx_estimated_absorpt_T_max   0.983
_shelx_estimated_absorpt_T_min   0.979
_exptl_absorpt_coefficient_mu    0.168
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8447
_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    1.813
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0449
_diffrn_reflns_av_unetI/netI     0.0433
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            7140
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.482
_diffrn_reflns_theta_min         3.066
_diffrn_ambient_temperature      153.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.991
_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                2172
_reflns_number_total             2425
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.322
_refine_diff_density_min         -0.242
_refine_diff_density_rms         0.063
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.158
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         2425
_refine_ls_number_restraints     18
_refine_ls_R_factor_all          0.0669
_refine_ls_R_factor_gt           0.0594
_refine_ls_restrained_S_all      1.165
_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)+(0.0567P)²+0.7237P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1384
_refine_ls_wR_factor_ref         0.1430
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All N(H,H,H,H) groups, All O(H,H) groups
2. Uiso/Uaniso restraints and constraints
O9A \\sim O9: within 1.7A with sigma of 0.01 and sigma for terminal atoms of
0.01
Uanis(O9A) \\sim Ueq, Uanis(O9) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
3. Others
 Sof(O9A)=Sof(H9AA)=Sof(H9AB)=1-FVAR(1)
 Sof(O9)=Sof(H9A)=Sof(H9B)=FVAR(1)
4.a Riding coordinates:
 N8(H8A,H8B,H8C,H8D), O9(H9A,H9B), O9A(H9AA,H9AB)
;
_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 0.0307(3) 0.43852(11) 0.17304(11) 0.0238(4) Uani 1 1 d . . . A 2
O3 O 1.1803(3) 0.71524(13) 0.11472(11) 0.0288(4) Uani 1 1 d . . . . .
O2 O 0.8453(3) 0.63113(12) 0.34219(10) 0.0230(4) Uani 1 1 d . . . . .
O5 O 1.4907(3) 0.80409(13) 0.33260(12) 0.0311(4) Uani 1 1 d . . . . .
N5 N 0.7530(3) 0.64210(13) 0.19760(12) 0.0185(4) Uani 1 1 d . . . . .
O6 O 1.1766(4) 0.74748(14) 0.41171(11) 0.0308(4) Uani 1 1 d . . . . .
N6 N 1.2692(4) 0.76530(14) 0.33783(13) 0.0229(4) Uani 1 1 d . . . B 1
N3 N 0.5044(4) 0.52967(13) 0.03170(12) 0.0201(4) Uani 1 1 d . . . . .
N7 N 1.2183(4) 0.76886(14) 0.17949(13) 0.0239(4) Uani 1 1 d . . . . .
N1 N 0.1905(4) 0.48418(14) 0.23617(13) 0.0219(4) Uani 1 1 d . . . . .
C1 C 0.3431(4) 0.49977(15) 0.10090(14) 0.0180(4) Uani 1 1 d . . . . .
C4 C 0.9076(4) 0.67152(15) 0.26445(14) 0.0177(4) Uani 1 1 d . . . . .
C3 C 0.5907(4) 0.57858(15) 0.23878(14) 0.0178(4) Uani 1 1 d . . . . .
N2 N 0.1273(4) 0.44874(13) 0.08967(13) 0.0218(4) Uani 1 1 d . . . . .
N4 N 0.6308(4) 0.56846(14) 0.32372(13) 0.0246(4) Uani 1 1 d . . . . .
O4 O 1.3306(4) 0.84611(14) 0.17347(14) 0.0448(6) Uani 1 1 d . . . . .
C5 C 1.1276(4) 0.73642(16) 0.26203(15) 0.0201(5) Uani 1 1 d . . . . .
C2 C 0.3813(4) 0.52331(15) 0.19218(14) 0.0183(4) Uani 1 1 d . . . . .
N8 N 0.3121(4) 0.25636(15) 0.48082(13) 0.0277(5) Uani 1 1 d . . . . .
H8A H 0.203301 0.243402 0.520774 0.033 Uiso 1 1 d R . . . .
H8B H 0.288421 0.219892 0.436214 0.033 Uiso 1 1 d R . . . .
H8C H 0.464401 0.246582 0.505014 0.033 Uiso 1 1 d R . . . .
H8D H 0.293131 0.315882 0.470334 0.033 Uiso 1 1 d R . . . .
O9 O 0.198(2) 0.4554(6) 0.4495(6) 0.061(2) Uani 0.61(2) 1 d . U P C 1
H9A H 0.142731 0.503931 0.476020 0.073 Uiso 0.61(2) 1 d R . P C 1
H9B H 0.184661 0.453131 0.394000 0.073 Uiso 0.61(2) 1 d R . P C 1
O9A O 0.323(4) 0.4664(7) 0.4727(7) 0.061(3) Uani 0.39(2) 1 d . U P C 2
H9AA H 0.392345 0.473947 0.423516 0.073 Uiso 0.39(2) 1 d R . P C 2
H9AB H 0.295585 0.520027 0.496026 0.073 Uiso 0.39(2) 1 d R . P C 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 N1 1.383(2) . ?
O1 N2 1.375(2) . ?
O3 N7 1.242(3) . ?
O2 C4 1.351(3) . ?
O2 N4 1.411(2) . ?
O5 N6 1.247(3) . ?
N5 C4 1.320(3) . ?
N5 C3 1.371(3) . ?
O6 N6 1.251(3) . ?
N6 C5 1.388(3) . ?
N3 N3 1.266(4) 3_665 ?
N3 C1 1.411(3) . ?
N7 O4 1.222(3) . ?
N7 C5 1.419(3) . ?
N1 C2 1.309(3) . ?
C1 N2 1.307(3) . ?
C1 C2 1.425(3) . ?
C4 C5 1.434(3) . ?
C3 N4 1.301(3) . ?
C3 C2 1.467(3) . ?
N8 H8A 0.8500 . ?
N8 H8B 0.8499 . ?
N8 H8C 0.8500 . ?
N8 H8D 0.8500 . ?
O9 H9A 0.8399 . ?
O9 H9B 0.8399 . ?
O9A H9AA 0.8398 . ?
O9A H9AB 0.8401 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 O1 N1 111.60(15) . . ?
C4 O2 N4 106.67(16) . . ?
C4 N5 C3 101.48(18) . . ?
O5 N6 O6 120.46(19) . . ?
O5 N6 C5 120.6(2) . . ?
O6 N6 C5 118.83(19) . . ?
N3 N3 C1 111.3(2) 3_665 . ?
O3 N7 C5 117.16(19) . . ?
O4 N7 O3 122.1(2) . . ?
O4 N7 C5 120.8(2) . . ?
C2 N1 O1 105.21(18) . . ?
N3 C1 C2 126.06(19) . . ?
N2 C1 N3 124.4(2) . . ?
N2 C1 C2 109.5(2) . . ?
O2 C4 C5 119.35(19) . . ?
N5 C4 O2 112.79(19) . . ?
N5 C4 C5 127.8(2) . . ?
N5 C3 C2 123.55(19) . . ?
N4 C3 N5 116.39(19) . . ?
N4 C3 C2 120.1(2) . . ?
C1 N2 O1 104.97(18) . . ?
C3 N4 O2 102.66(18) . . ?
N6 C5 N7 117.47(19) . . ?
N6 C5 C4 122.5(2) . . ?
N7 C5 C4 119.88(19) . . ?
N1 C2 C1 108.66(19) . . ?
N1 C2 C3 120.3(2) . . ?
C1 C2 C3 131.0(2) . . ?
H8A N8 H8B 111.2 . . ?
H8A N8 H8C 104.9 . . ?
H8A N8 H8D 105.6 . . ?
H8B N8 H8C 110.2 . . ?
H8B N8 H8D 115.1 . . ?
H8C N8 H8D 109.3 . . ?
H9A O9 H9B 119.4 . . ?
H9AA O9A H9AB 109.9 . . ?

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 C2 C1 -1.4(2) . . . . ?
O1 N1 C2 C3 179.93(18) . . . . ?
O3 N7 C5 N6 148.9(2) . . . . ?
O3 N7 C5 C4 -27.4(3) . . . . ?
O2 C4 C5 N6 -4.8(3) . . . . ?
O2 C4 C5 N7 171.20(19) . . . . ?
O5 N6 C5 N7 -11.9(3) . . . . ?
O5 N6 C5 C4 164.2(2) . . . . ?
N5 C4 C5 N6 177.2(2) . . . . ?
N5 C4 C5 N7 -6.8(3) . . . . ?
N5 C3 N4 O2 -0.6(2) . . . . ?
N5 C3 C2 N1 -161.8(2) . . . . ?
N5 C3 C2 C1 19.9(4) . . . . ?
O6 N6 C5 N7 171.59(19) . . . . ?
O6 N6 C5 C4 -12.3(3) . . . . ?
N3 N3 C1 N2 -30.1(3) 3_665 . . . ?
N3 N3 C1 C2 152.8(2) 3_665 . . . ?
N3 C1 N2 O1 -178.36(19) . . . . ?
N3 C1 C2 N1 178.9(2) . . . . ?
N3 C1 C2 C3 -2.6(4) . . . . ?
N1 O1 N2 C1 0.0(2) . . . . ?
C4 O2 N4 C3 0.0(2) . . . . ?
C4 N5 C3 N4 1.0(3) . . . . ?
C4 N5 C3 C2 -178.75(19) . . . . ?
C3 N5 C4 O2 -1.0(2) . . . . ?
C3 N5 C4 C5 177.1(2) . . . . ?
N2 O1 N1 C2 0.9(2) . . . . ?
N2 C1 C2 N1 1.5(3) . . . . ?
N2 C1 C2 C3 180.0(2) . . . . ?
N4 O2 C4 N5 0.7(2) . . . . ?
N4 O2 C4 C5 -177.59(18) . . . . ?
N4 C3 C2 N1 18.4(3) . . . . ?
N4 C3 C2 C1 -159.9(2) . . . . ?
O4 N7 C5 N6 -30.6(3) . . . . ?
O4 N7 C5 C4 153.2(2) . . . . ?
C2 C1 N2 O1 -0.9(2) . . . . ?
C2 C3 N4 O2 179.16(18) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
