# Electronic Supplementary Material (ESI) for CrystEngComm.
# 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_32060301_0m
_database_code_depnum_ccdc_archive 'CCDC 2120743'
loop_
_audit_author_name
_audit_author_address
'Miquel Barcelo-Oliver'
;University of the Balearic Islands
Spain
;
_audit_update_record             
;
2022-11-14 deposited with the CCDC.	2022-11-24 downloaded from the CCDC.
;
_audit_creation_date             2022-11-14
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2019/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C7 H9 N3 O2'
_chemical_formula_sum            'C7 H9 N3 O2'
_chemical_formula_weight         167.17
_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           13
_space_group_name_H-M_alt        'P 1 2/n 1'
_space_group_name_Hall           '-P 2yac'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z-1/2'

_cell_length_a                   8.9457(6)
_cell_length_b                   9.3395(6)
_cell_length_c                   8.9601(6)
_cell_angle_alpha                90
_cell_angle_beta                 92.480(2)
_cell_angle_gamma                90
_cell_volume                     747.90(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8319
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.30
_cell_measurement_theta_min      3.15
_shelx_estimated_absorpt_T_max   0.977
_shelx_estimated_absorpt_T_min   0.972
_exptl_absorpt_coefficient_mu    0.112
_exptl_absorpt_correction_T_max  0.7253
_exptl_absorpt_correction_T_min  0.6907
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS-2016/2 (Bruker AXS Inc.)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.485
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             352
_exptl_crystal_size_max          0.251
_exptl_crystal_size_mid          0.237
_exptl_crystal_size_min          0.212
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0465
_diffrn_reflns_av_unetI/netI     0.0259
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            12672
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.315
_diffrn_reflns_theta_min         3.150
_diffrn_ambient_temperature      100.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker D8 Venture Photon 100 CMOS'
_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                1699
_reflns_number_total             1865
_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       'Bruker SAINT'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_refine_diff_density_max         0.765
_refine_diff_density_min         -0.358
_refine_diff_density_rms         0.078
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     113
_refine_ls_number_reflns         1865
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0593
_refine_ls_R_factor_gt           0.0554
_refine_ls_restrained_S_all      1.049
_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)+(0.0973P)²+0.4563P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1487
_refine_ls_wR_factor_ref         0.1524
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C4(H4A,H4B)
2.b Aromatic/amide H refined with riding coordinates:
 C4'(H4'), C5'(H5'), C6'(H6')
2.c Tetrahedral OH refined with riding coordinates:
 O1(H1)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.08523(14) 0.30025(13) 0.33151(15) 0.0322(4) Uani 1 1 d . . . . .
H1 H 0.148819 0.260542 0.389511 0.039 Uiso 1 1 calc R U . . .
O2 O 0.18456(11) 0.49969(10) 0.43145(11) 0.0137(3) Uani 1 1 d . . . . .
C2 C 0.09634(15) 0.43804(15) 0.34505(15) 0.0126(3) Uani 1 1 d . . . . .
C3 C -0.01487(16) 0.51144(14) 0.23952(15) 0.0126(3) Uani 1 1 d . . . . .
H3A H -0.116636 0.482551 0.266715 0.015 Uiso 1 1 calc R U . . .
H3B H 0.000206 0.475065 0.137483 0.015 Uiso 1 1 calc R U . . .
C4 C -0.00937(15) 0.67381(15) 0.23468(15) 0.0128(3) Uani 1 1 d . . . . .
H4A H -0.035083 0.714320 0.332404 0.015 Uiso 1 1 calc R U . . .
H4B H 0.092191 0.706733 0.211358 0.015 Uiso 1 1 calc R U . . .
N5 N -0.11802(14) 0.71950(13) 0.11829(13) 0.0137(3) Uani 1 1 d . . . . .
H5 H -0.173(3) 0.650(3) 0.065(3) 0.036(6) Uiso 1 1 d . . . . .
N1' N -0.26113(13) 0.88003(13) -0.01758(13) 0.0119(3) Uani 1 1 d . . . . .
C2' C -0.15296(15) 0.85788(14) 0.09012(15) 0.0112(3) Uani 1 1 d . . . . .
N3' N -0.08129(13) 0.96185(14) 0.16707(13) 0.0127(3) Uani 1 1 d . . . . .
C4' C -0.12244(16) 1.09555(15) 0.13273(15) 0.0146(3) Uani 1 1 d . . . . .
H4' H -0.073155 1.171850 0.184850 0.018 Uiso 1 1 calc R U . . .
C5' C -0.23403(16) 1.12990(15) 0.02434(16) 0.0134(3) Uani 1 1 d . . . . .
H5' H -0.261962 1.226066 0.002718 0.016 Uiso 1 1 calc R U . . .
C6' C -0.30102(15) 1.01504(15) -0.04925(15) 0.0122(3) Uani 1 1 d . . . . .
H6' H -0.377262 1.032416 -0.124170 0.015 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 H1 0.8400 . ?
O1 C2 1.2960(17) . ?
O2 C2 1.2251(17) . ?
C2 C3 1.5075(18) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C4 1.5179(19) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 N5 1.4583(17) . ?
N5 H5 0.93(3) . ?
N5 C2' 1.3509(17) . ?
N1' C2' 1.3526(18) . ?
N1' C6' 1.3375(17) . ?
C2' N3' 1.3384(18) . ?
N3' C4' 1.3340(19) . ?
C4' H4' 0.9500 . ?
C4' C5' 1.399(2) . ?
C5' H5' 0.9500 . ?
C5' C6' 1.3822(19) . ?
C6' H6' 0.9500 . ?

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 . . ?
O1 C2 C3 110.30(12) . . ?
O2 C2 O1 124.79(13) . . ?
O2 C2 C3 124.91(12) . . ?
C2 C3 H3A 108.1 . . ?
C2 C3 H3B 108.1 . . ?
C2 C3 C4 116.80(11) . . ?
H3A C3 H3B 107.3 . . ?
C4 C3 H3A 108.1 . . ?
C4 C3 H3B 108.1 . . ?
C3 C4 H4A 110.3 . . ?
C3 C4 H4B 110.3 . . ?
H4A C4 H4B 108.6 . . ?
N5 C4 C3 106.93(11) . . ?
N5 C4 H4A 110.3 . . ?
N5 C4 H4B 110.3 . . ?
C4 N5 H5 118.8(15) . . ?
C2' N5 C4 123.73(12) . . ?
C2' N5 H5 117.3(16) . . ?
C6' N1' C2' 118.14(12) . . ?
N5 C2' N1' 115.61(12) . . ?
N3' C2' N5 119.74(13) . . ?
N3' C2' N1' 124.65(13) . . ?
C4' N3' C2' 116.04(12) . . ?
N3' C4' H4' 118.1 . . ?
N3' C4' C5' 123.78(13) . . ?
C5' C4' H4' 118.1 . . ?
C4' C5' H5' 122.1 . . ?
C6' C5' C4' 115.76(13) . . ?
C6' C5' H5' 122.1 . . ?
N1' C6' C5' 121.62(13) . . ?
N1' C6' H6' 119.2 . . ?
C5' C6' H6' 119.2 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O1 H1 N1' 0.84 1.73 2.5281(16) 156.8 4_666 yes
N5 H5 O2 0.93(3) 2.21(3) 3.1394(16) 175(2) 4_565 yes
C4' H4' O1 0.95 2.24 3.1611(18) 163.5 1_565 yes
C6' H6' N3' 0.95 2.56 3.4988(18) 171.3 4_575 yes

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 C2 C3 C4 -176.24(13) . . . . ?
O2 C2 C3 C4 3.8(2) . . . . ?
C2 C3 C4 N5 175.87(11) . . . . ?
C3 C4 N5 C2' 174.41(12) . . . . ?
C4 N5 C2' N1' -177.14(12) . . . . ?
C4 N5 C2' N3' 3.0(2) . . . . ?
N5 C2' N3' C4' -179.91(12) . . . . ?
N1' C2' N3' C4' 0.22(19) . . . . ?
C2' N1' C6' C5' 0.4(2) . . . . ?
C2' N3' C4' C5' 0.5(2) . . . . ?
N3' C4' C5' C6' -0.7(2) . . . . ?
C4' C5' C6' N1' 0.21(19) . . . . ?
C6' N1' C2' N5 179.48(11) . . . . ?
C6' N1' C2' N3' -0.6(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_32061801_0m
_database_code_depnum_ccdc_archive 'CCDC 2120746'
loop_
_audit_author_name
_audit_author_address
'Miquel Barcelo-Oliver'
;University of the Balearic Islands
Spain
;
_audit_update_record             
;
2022-11-14 deposited with the CCDC.	2022-11-24 downloaded from the CCDC.
;
_audit_creation_date             2022-11-14
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2019/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C9 H13 N3 O2'
_chemical_formula_sum            'C9 H13 N3 O2'
_chemical_formula_weight         195.22
_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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   6.9655(3)
_cell_length_b                   9.4546(5)
_cell_length_c                   14.4579(7)
_cell_angle_alpha                90
_cell_angle_beta                 90.205(2)
_cell_angle_gamma                90
_cell_volume                     952.13(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9994
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.32
_cell_measurement_theta_min      2.57
_shelx_estimated_absorpt_T_max   0.982
_shelx_estimated_absorpt_T_min   0.974
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_T_max  0.7399
_exptl_absorpt_correction_T_min  0.7191
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS-2016/2 (Bruker AXS Inc.)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.362
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             416
_exptl_crystal_size_max          0.267
_exptl_crystal_size_mid          0.236
_exptl_crystal_size_min          0.189
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0329
_diffrn_reflns_av_unetI/netI     0.0185
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            21931
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.343
_diffrn_reflns_theta_min         2.574
_diffrn_ambient_temperature      100.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker D8 Venture Photon 100 CMOS'
_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                2081
_reflns_number_total             2373
_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       'Bruker SAINT'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_refine_diff_density_max         0.290
_refine_diff_density_min         -0.302
_refine_diff_density_rms         0.054
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     135
_refine_ls_number_reflns         2373
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0494
_refine_ls_R_factor_gt           0.0417
_refine_ls_restrained_S_all      1.075
_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)+(0.0405P)²+0.5430P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0954
_refine_ls_wR_factor_ref         0.0990
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C4(H4A,H4B), C5(H5A,H5B), C6(H6A,H6B)
2.b Aromatic/amide H refined with riding coordinates:
 C4'(H4'), C5'(H5'), C6'(H6')
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 1.25823(13) 0.03082(10) 0.85718(6) 0.0191(2) Uani 1 1 d . . . . .
H1 H 1.211(3) -0.025(2) 0.9062(14) 0.044(5) Uiso 1 1 d . . . . .
O2 O 0.98925(12) -0.04497(10) 0.78841(6) 0.0175(2) Uani 1 1 d . . . . .
C2 C 1.13864(16) 0.02140(12) 0.78588(8) 0.0127(2) Uani 1 1 d . . . . .
C3 C 1.21107(17) 0.09872(14) 0.70137(8) 0.0159(3) Uani 1 1 d . . . . .
H3A H 1.335513 0.056980 0.682890 0.019 Uiso 1 1 calc R U . . .
H3B H 1.234588 0.198793 0.718076 0.019 Uiso 1 1 calc R U . . .
C4 C 1.07468(16) 0.09416(13) 0.61860(8) 0.0135(2) Uani 1 1 d . . . . .
H4A H 1.028682 -0.004141 0.610420 0.016 Uiso 1 1 calc R U . . .
H4B H 1.146939 0.120435 0.562320 0.016 Uiso 1 1 calc R U . . .
C5 C 0.90087(17) 0.19176(13) 0.62718(8) 0.0137(2) Uani 1 1 d . . . . .
H5A H 0.828339 0.167429 0.683755 0.016 Uiso 1 1 calc R U . . .
H5B H 0.944897 0.290950 0.632894 0.016 Uiso 1 1 calc R U . . .
C6 C 0.77006(16) 0.17772(13) 0.54313(8) 0.0131(2) Uani 1 1 d . . . . .
H6A H 0.843762 0.199286 0.486429 0.016 Uiso 1 1 calc R U . . .
H6B H 0.723246 0.079100 0.538478 0.016 Uiso 1 1 calc R U . . .
N7 N 0.60709(14) 0.27326(11) 0.54958(7) 0.0142(2) Uani 1 1 d . . . . .
H7 H 0.597(2) 0.3306(17) 0.5962(11) 0.018(4) Uiso 1 1 d . . . . .
N1' N 0.47625(15) 0.17938(11) 0.41587(7) 0.0143(2) Uani 1 1 d . . . . .
C2' C 0.46611(16) 0.27433(12) 0.48593(8) 0.0121(2) Uani 1 1 d . . . . .
N3' N 0.32402(14) 0.37124(11) 0.49707(7) 0.0134(2) Uani 1 1 d . . . . .
C4' C 0.18341(17) 0.36986(13) 0.43398(8) 0.0149(2) Uani 1 1 d . . . . .
H4' H 0.083119 0.437447 0.439229 0.018 Uiso 1 1 calc R U . . .
C5' C 0.17696(17) 0.27488(13) 0.36152(8) 0.0155(3) Uani 1 1 d . . . . .
H5' H 0.074482 0.273866 0.317986 0.019 Uiso 1 1 calc R U . . .
C6' C 0.32957(18) 0.18104(13) 0.35631(8) 0.0153(2) Uani 1 1 d . . . . .
H6' H 0.329651 0.113933 0.307400 0.018 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 H1 0.94(2) . ?
O1 C2 1.3260(14) . ?
O2 C2 1.2158(15) . ?
C2 C3 1.5120(16) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C4 1.5259(15) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C5 1.5277(16) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5 C6 1.5221(15) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C6 N7 1.4540(15) . ?
N7 H7 0.868(17) . ?
N7 C2' 1.3434(15) . ?
N1' C2' 1.3555(15) . ?
N1' C6' 1.3339(15) . ?
C2' N3' 1.3587(15) . ?
N3' C4' 1.3361(15) . ?
C4' H4' 0.9500 . ?
C4' C5' 1.3803(17) . ?
C5' H5' 0.9500 . ?
C5' C6' 1.3869(18) . ?
C6' H6' 0.9500 . ?

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 109.2(12) . . ?
O1 C2 C3 112.66(10) . . ?
O2 C2 O1 123.13(11) . . ?
O2 C2 C3 124.19(10) . . ?
C2 C3 H3A 108.7 . . ?
C2 C3 H3B 108.7 . . ?
C2 C3 C4 114.30(10) . . ?
H3A C3 H3B 107.6 . . ?
C4 C3 H3A 108.7 . . ?
C4 C3 H3B 108.7 . . ?
C3 C4 H4A 108.7 . . ?
C3 C4 H4B 108.7 . . ?
C3 C4 C5 114.24(10) . . ?
H4A C4 H4B 107.6 . . ?
C5 C4 H4A 108.7 . . ?
C5 C4 H4B 108.7 . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 108.1 . . ?
C6 C5 C4 110.78(9) . . ?
C6 C5 H5A 109.5 . . ?
C6 C5 H5B 109.5 . . ?
C5 C6 H6A 109.4 . . ?
C5 C6 H6B 109.4 . . ?
H6A C6 H6B 108.0 . . ?
N7 C6 C5 111.09(9) . . ?
N7 C6 H6A 109.4 . . ?
N7 C6 H6B 109.4 . . ?
C6 N7 H7 120.3(10) . . ?
C2' N7 C6 121.98(10) . . ?
C2' N7 H7 117.7(10) . . ?
C6' N1' C2' 115.64(10) . . ?
N7 C2' N1' 117.84(10) . . ?
N7 C2' N3' 117.05(10) . . ?
N1' C2' N3' 125.11(10) . . ?
C4' N3' C2' 116.42(10) . . ?
N3' C4' H4' 118.4 . . ?
N3' C4' C5' 123.11(11) . . ?
C5' C4' H4' 118.4 . . ?
C4' C5' H5' 122.1 . . ?
C4' C5' C6' 115.75(11) . . ?
C6' C5' H5' 122.1 . . ?
N1' C6' C5' 123.91(11) . . ?
N1' C6' H6' 118.0 . . ?
C5' C6' H6' 118.0 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C4' H4' O1 0.95 2.57 3.2958(15) 133.5 4_465 yes

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 C2 C3 C4 -178.26(10) . . . . ?
O2 C2 C3 C4 3.18(17) . . . . ?
C2 C3 C4 C5 75.41(13) . . . . ?
C3 C4 C5 C6 -178.48(10) . . . . ?
C4 C5 C6 N7 -178.38(10) . . . . ?
C5 C6 N7 C2' -176.22(10) . . . . ?
C6 N7 C2' N1' 2.14(17) . . . . ?
C6 N7 C2' N3' -177.82(10) . . . . ?
N7 C2' N3' C4' -179.13(11) . . . . ?
N1' C2' N3' C4' 0.92(17) . . . . ?
C2' N1' C6' C5' 1.97(18) . . . . ?
C2' N3' C4' C5' 1.10(18) . . . . ?
N3' C4' C5' C6' -1.44(18) . . . . ?
C4' C5' C6' N1' -0.20(18) . . . . ?
C6' N1' C2' N7 177.65(11) . . . . ?
C6' N1' C2' N3' -2.39(17) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1_a
_database_code_depnum_ccdc_archive 'CCDC 2120745'
loop_
_audit_author_name
_audit_author_address
'Miquel Barcelo-Oliver'
;University of the Balearic Islands
Spain
;
_audit_update_record             
;
2022-11-15 deposited with the CCDC.	2022-11-24 downloaded from the CCDC.
;
_audit_creation_date             2022-11-15
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2019/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C8 H12 N3 O2, N O3'
_chemical_formula_sum            'C8 H12 N4 O5'
_chemical_formula_weight         244.22
_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 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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                   9.8280(10)
_cell_length_b                   14.0136(14)
_cell_length_c                   15.9826(16)
_cell_angle_alpha                101.543(3)
_cell_angle_beta                 96.517(3)
_cell_angle_gamma                94.398(2)
_cell_volume                     2131.6(4)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9738
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      66.492
_cell_measurement_theta_min      5.311
_shelx_estimated_absorpt_T_max   0.778
_shelx_estimated_absorpt_T_min   0.614
_exptl_absorpt_coefficient_mu    1.103
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_correction_T_min  0.3844
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1442 before and 0.1014 after correction.
The Ratio of minimum to maximum transmission is 0.5106.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.522
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             1024
_exptl_crystal_size_max          0.49
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.24
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0634
_diffrn_reflns_av_unetI/netI     0.0578
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            33594
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        66.558
_diffrn_reflns_theta_max         66.558
_diffrn_reflns_theta_min         2.847
_diffrn_ambient_temperature      100.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                7193
_reflns_number_total             7442
_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       'Bruker Apex3, 2016'
_computing_data_collection       'Bruker Apex3, 2016'
_computing_data_reduction        'SAINT v8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.362
_refine_diff_density_min         -0.301
_refine_diff_density_rms         0.070
_refine_ls_extinction_coef       0.0095(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2019/1 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     618
_refine_ls_number_reflns         7442
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0547
_refine_ls_R_factor_gt           0.0535
_refine_ls_restrained_S_all      1.069
_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)+(0.0990P)²+0.6163P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1558
_refine_ls_wR_factor_ref         0.1572
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C3B(H3BA,H3BB), C4B(H4BA,H4BB), C5B(H5BA,H5BB), C3D(H3DA,H3DB), C4D(H4DA,
 H4DB), C5D(H5DA,H5DB), C3C(H3CA,H3CB), C4C(H4CA,H4CB), C5C(H5CA,H5CB),
 C3A(H3AA,H3AB), C4A(H4AA,H4AB), C5A(H5AA,H5AB)
2.b Aromatic/amide H refined with riding coordinates:
 N6B(H6B), N1B'(H1B'), C4B'(H4B'), C5B'(H5B'), C6B'(H6B'), N6D(H6D),
 N1D'(H1D'), C4D'(H4D'), C5D'(H5D'), C6D'(H6D'), N6C(H6C), N1C'(H1C'),
 C4C'(H4C'), C5C'(H5C'), C6C'(H6C'), N6A(H6A), N1A'(H1A'), C4A'(H4A'),
 C5A'(H5A'), C6A'(H6A')
2.c Idealised tetrahedral OH refined as rotating group:
 O1B(H1B), O1D(H1D), O1C(H1C), O1A(H1A)
;
_atom_sites_solution_hydrogens   geom
_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
O1B O 0.94144(11) 0.36594(10) 0.87559(8) 0.0344(3) Uani 1 1 d . . . . .
H1B H 0.888332 0.358900 0.912035 0.052 Uiso 1 1 calc R U . . .
C2B C 0.87675(15) 0.40315(11) 0.81430(10) 0.0270(3) Uani 1 1 d . . . . .
O2B O 0.75656(11) 0.41846(9) 0.81131(8) 0.0325(3) Uani 1 1 d . . . . .
C3B C 0.96835(16) 0.42467(13) 0.74948(11) 0.0301(4) Uani 1 1 d . . . . .
H3BA H 1.025651 0.369879 0.736134 0.036 Uiso 1 1 calc R U . . .
H3BB H 1.031149 0.484435 0.775797 0.036 Uiso 1 1 calc R U . . .
C4B C 0.89113(16) 0.43936(11) 0.66568(10) 0.0280(3) Uani 1 1 d . . . . .
H4BA H 0.957577 0.462723 0.630233 0.034 Uiso 1 1 calc R U . . .
H4BB H 0.827255 0.490027 0.678628 0.034 Uiso 1 1 calc R U . . .
C5B C 0.80965(16) 0.34395(12) 0.61491(10) 0.0275(3) Uani 1 1 d . . . . .
H5BA H 0.872575 0.291909 0.607106 0.033 Uiso 1 1 calc R U . . .
H5BB H 0.738159 0.323940 0.648686 0.033 Uiso 1 1 calc R U . . .
N6B N 0.74368(13) 0.35258(10) 0.53046(9) 0.0271(3) Uani 1 1 d . . . . .
H6B H 0.655575 0.360983 0.524198 0.033 Uiso 1 1 calc R U . . .
N1B' N 0.74073(13) 0.34998(10) 0.38539(9) 0.0276(3) Uani 1 1 d . . . . .
H1B' H 0.652539 0.358161 0.382096 0.033 Uiso 1 1 calc R U . . .
C2B' C 0.81182(16) 0.34820(11) 0.46269(10) 0.0261(3) Uani 1 1 d . . . . .
N3B' N 0.94819(13) 0.34067(10) 0.47171(9) 0.0282(3) Uani 1 1 d . . . . .
C4B' C 1.00890(16) 0.33225(12) 0.40084(11) 0.0307(4) Uani 1 1 d . . . . .
H4B' H 1.105219 0.327267 0.406181 0.037 Uiso 1 1 calc R U . . .
C5B' C 0.94021(17) 0.33023(12) 0.31892(11) 0.0319(4) Uani 1 1 d . . . . .
H5B' H 0.987287 0.322797 0.269640 0.038 Uiso 1 1 calc R U . . .
C6B' C 0.80277(17) 0.33942(12) 0.31297(11) 0.0301(4) Uani 1 1 d . . . . .
H6B' H 0.750999 0.338442 0.258807 0.036 Uiso 1 1 calc R U . . .
O1D O 0.68722(11) 0.09206(9) 0.95934(7) 0.0322(3) Uani 1 1 d . . . . .
H1D H 0.636605 0.097959 0.998661 0.048 Uiso 1 1 calc R U . . .
C2D C 0.63130(15) 0.12889(11) 0.89542(10) 0.0264(3) Uani 1 1 d . . . . .
O2D O 0.51756(11) 0.15797(9) 0.89270(7) 0.0311(3) Uani 1 1 d . . . . .
C3D C 0.72543(15) 0.13327(12) 0.82785(11) 0.0279(3) Uani 1 1 d . . . . .
H3DA H 0.755854 0.067502 0.809237 0.033 Uiso 1 1 calc R U . . .
H3DB H 0.808276 0.178672 0.854139 0.033 Uiso 1 1 calc R U . . .
C4D C 0.66079(15) 0.16640(11) 0.74887(10) 0.0267(3) Uani 1 1 d . . . . .
H4DA H 0.734257 0.186928 0.716692 0.032 Uiso 1 1 calc R U . . .
H4DB H 0.609963 0.223636 0.767323 0.032 Uiso 1 1 calc R U . . .
C5D C 0.56238(16) 0.08457(11) 0.68985(10) 0.0263(3) Uani 1 1 d . . . . .
H5DA H 0.612584 0.026343 0.674174 0.032 Uiso 1 1 calc R U . . .
H5DB H 0.487069 0.066265 0.721641 0.032 Uiso 1 1 calc R U . . .
N6D N 0.50288(13) 0.11201(10) 0.61113(9) 0.0271(3) Uani 1 1 d . . . . .
H6D H 0.417990 0.128229 0.607789 0.033 Uiso 1 1 calc R U . . .
N1D' N 0.50814(13) 0.14015(9) 0.47366(9) 0.0269(3) Uani 1 1 d . . . . .
H1D' H 0.424417 0.158272 0.474162 0.032 Uiso 1 1 calc R U . . .
C2D' C 0.57166(16) 0.11349(11) 0.54425(10) 0.0251(3) Uani 1 1 d . . . . .
N3D' N 0.70105(13) 0.08726(10) 0.54684(9) 0.0283(3) Uani 1 1 d . . . . .
C4D' C 0.76242(16) 0.08735(12) 0.47684(11) 0.0297(4) Uani 1 1 d . . . . .
H4D' H 0.853461 0.068815 0.477655 0.036 Uiso 1 1 calc R U . . .
C5D' C 0.70145(17) 0.11300(12) 0.40201(11) 0.0304(4) Uani 1 1 d . . . . .
H5D' H 0.748789 0.112038 0.353266 0.036 Uiso 1 1 calc R U . . .
C6D' C 0.57141(17) 0.13932(11) 0.40251(10) 0.0289(3) Uani 1 1 d . . . . .
H6D' H 0.525052 0.157039 0.353288 0.035 Uiso 1 1 calc R U . . .
O1C O 0.31635(11) 0.42824(9) 0.51261(8) 0.0320(3) Uani 1 1 d . . . . .
H1C H 0.364133 0.416927 0.472038 0.048 Uiso 1 1 calc R U . . .
C2C C 0.36763(15) 0.38910(12) 0.57669(10) 0.0279(4) Uani 1 1 d . . . . .
O2C O 0.47620(11) 0.35257(9) 0.57835(8) 0.0333(3) Uani 1 1 d . . . . .
C3C C 0.27378(16) 0.39160(12) 0.64546(11) 0.0295(4) Uani 1 1 d . . . . .
H3CA H 0.187891 0.348880 0.620571 0.035 Uiso 1 1 calc R U . . .
H3CB H 0.248869 0.459217 0.662695 0.035 Uiso 1 1 calc R U . . .
C4C C 0.33544(16) 0.35899(12) 0.72561(11) 0.0280(3) Uani 1 1 d . . . . .
H4CA H 0.389006 0.302989 0.708126 0.034 Uiso 1 1 calc R U . . .
H4CB H 0.260022 0.336311 0.755316 0.034 Uiso 1 1 calc R U . . .
C5C C 0.42927(16) 0.44091(12) 0.78832(11) 0.0285(3) Uani 1 1 d . . . . .
H5CA H 0.503021 0.465129 0.758154 0.034 Uiso 1 1 calc R U . . .
H5CB H 0.375041 0.496046 0.807445 0.034 Uiso 1 1 calc R U . . .
N6C N 0.49154(13) 0.40811(10) 0.86364(9) 0.0282(3) Uani 1 1 d . . . . .
H6C H 0.577753 0.394769 0.865755 0.034 Uiso 1 1 calc R U . . .
N1C' N 0.48905(14) 0.36298(10) 0.99494(9) 0.0282(3) Uani 1 1 d . . . . .
H1C' H 0.574237 0.348303 0.992846 0.034 Uiso 1 1 calc R U . . .
C2C' C 0.42367(16) 0.39749(11) 0.92924(10) 0.0267(3) Uani 1 1 d . . . . .
N3C' N 0.29417(13) 0.42193(10) 0.93044(9) 0.0298(3) Uani 1 1 d . . . . .
C4C' C 0.23311(16) 0.41082(12) 0.99874(11) 0.0306(4) Uani 1 1 d . . . . .
H4C' H 0.141965 0.428575 1.000650 0.037 Uiso 1 1 calc R U . . .
C5C' C 0.29453(17) 0.37477(12) 1.06764(11) 0.0321(4) Uani 1 1 d . . . . .
H5C' H 0.247257 0.367373 1.114970 0.039 Uiso 1 1 calc R U . . .
C6C' C 0.42573(17) 0.35073(12) 1.06351(11) 0.0305(4) Uani 1 1 d . . . . .
H6C' H 0.472419 0.325556 1.108461 0.037 Uiso 1 1 calc R U . . .
O1A O 1.05454(11) 0.16346(10) 0.59192(8) 0.0345(3) Uani 1 1 d . . . . .
H1A H 1.107371 0.164617 0.554265 0.052 Uiso 1 1 calc R U . . .
C2A C 1.11687(15) 0.12980(11) 0.65641(10) 0.0265(3) Uani 1 1 d . . . . .
O2A O 1.23671(11) 0.11317(9) 0.66100(8) 0.0315(3) Uani 1 1 d . . . . .
C3A C 1.02292(16) 0.11417(12) 0.72127(11) 0.0290(4) Uani 1 1 d . . . . .
H3AA H 0.946603 0.063900 0.692673 0.035 Uiso 1 1 calc R U . . .
H3AB H 0.982336 0.175911 0.741123 0.035 Uiso 1 1 calc R U . . .
C4A C 1.09322(16) 0.08211(12) 0.79938(10) 0.0280(3) Uani 1 1 d . . . . .
H4AA H 1.149696 0.028387 0.780055 0.034 Uiso 1 1 calc R U . . .
H4AB H 1.022561 0.056914 0.831203 0.034 Uiso 1 1 calc R U . . .
C5A C 1.18479(16) 0.16712(12) 0.85914(10) 0.0284(3) Uani 1 1 d . . . . .
H5AA H 1.258703 0.189083 0.827961 0.034 Uiso 1 1 calc R U . . .
H5AB H 1.129128 0.222497 0.874326 0.034 Uiso 1 1 calc R U . . .
N6A N 1.24739(13) 0.14235(10) 0.93835(9) 0.0296(3) Uani 1 1 d . . . . .
H6A H 1.333007 0.127610 0.941697 0.036 Uiso 1 1 calc R U . . .
N1A' N 1.24961(14) 0.12850(10) 1.08015(9) 0.0289(3) Uani 1 1 d . . . . .
H1A' H 1.337403 0.119384 1.081991 0.035 Uiso 1 1 calc R U . . .
C2A' C 1.17922(16) 0.14129(11) 1.00575(11) 0.0278(3) Uani 1 1 d . . . . .
N3A' N 1.04456(14) 0.15415(10) 0.99942(9) 0.0309(3) Uani 1 1 d . . . . .
C4A' C 0.98371(17) 0.15408(12) 1.06974(11) 0.0324(4) Uani 1 1 d . . . . .
H4A' H 0.888506 0.162878 1.066348 0.039 Uiso 1 1 calc R U . . .
C5A' C 1.05072(18) 0.14193(12) 1.14799(11) 0.0334(4) Uani 1 1 d . . . . .
H5A' H 1.003485 0.142267 1.196697 0.040 Uiso 1 1 calc R U . . .
C6A' C 1.18753(18) 0.12951(12) 1.15128(11) 0.0321(4) Uani 1 1 d . . . . .
H6A' H 1.238492 0.121657 1.203213 0.038 Uiso 1 1 calc R U . . .
N1E N 0.82109(14) 0.36044(10) 1.06522(9) 0.0292(3) Uani 1 1 d . . . . .
O2E O 0.76548(11) 0.34286(9) 0.98575(7) 0.0307(3) Uani 1 1 d . . . . .
O3E O 0.94577(12) 0.38300(10) 1.08253(8) 0.0404(3) Uani 1 1 d . . . . .
O4E O 0.74519(13) 0.35336(10) 1.12083(8) 0.0407(3) Uani 1 1 d . . . . .
N5E N 0.42343(14) -0.10476(10) 0.84449(9) 0.0309(3) Uani 1 1 d . . . . .
O6E O 0.29790(13) -0.11488(11) 0.82513(9) 0.0459(4) Uani 1 1 d . . . . .
O7E O 0.50464(13) -0.08583(9) 0.79496(8) 0.0383(3) Uani 1 1 d . . . . .
O8E O 0.47498(12) -0.11457(10) 0.91991(8) 0.0383(3) Uani 1 1 d . . . . .
N9E N 0.59534(13) -0.34501(10) 0.69163(9) 0.0296(3) Uani 1 1 d . . . . .
O10E O 0.52484(13) -0.31198(11) 0.74805(8) 0.0427(3) Uani 1 1 d . . . . .
O11E O 0.53225(12) -0.38074(10) 0.61539(8) 0.0395(3) Uani 1 1 d . . . . .
O12E O 0.72080(12) -0.34492(10) 0.70565(9) 0.0395(3) Uani 1 1 d . . . . .
N13E N 0.82458(14) -0.13344(10) 0.59825(9) 0.0298(3) Uani 1 1 d . . . . .
O14E O 0.76737(11) -0.17319(9) 0.52122(7) 0.0315(3) Uani 1 1 d . . . . .
O15E O 0.75001(13) -0.11791(10) 0.65591(8) 0.0407(3) Uani 1 1 d . . . . .
O16E O 0.95044(12) -0.11283(10) 0.61193(9) 0.0411(3) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1B H1B 0.8400 . ?
O1B C2B 1.323(2) . ?
C2B O2B 1.2140(19) . ?
C2B C3B 1.507(2) . ?
C3B H3BA 0.9900 . ?
C3B H3BB 0.9900 . ?
C3B C4B 1.522(2) . ?
C4B H4BA 0.9900 . ?
C4B H4BB 0.9900 . ?
C4B C5B 1.530(2) . ?
C5B H5BA 0.9900 . ?
C5B H5BB 0.9900 . ?
C5B N6B 1.461(2) . ?
N6B H6B 0.8800 . ?
N6B C2B' 1.330(2) . ?
N1B' H1B' 0.8800 . ?
N1B' C2B' 1.354(2) . ?
N1B' C6B' 1.356(2) . ?
C2B' N3B' 1.346(2) . ?
N3B' C4B' 1.328(2) . ?
C4B' H4B' 0.9500 . ?
C4B' C5B' 1.397(2) . ?
C5B' H5B' 0.9500 . ?
C5B' C6B' 1.361(2) . ?
C6B' H6B' 0.9500 . ?
O1D H1D 0.8400 . ?
O1D C2D 1.319(2) . ?
C2D O2D 1.2179(19) . ?
C2D C3D 1.507(2) . ?
C3D H3DA 0.9900 . ?
C3D H3DB 0.9900 . ?
C3D C4D 1.520(2) . ?
C4D H4DA 0.9900 . ?
C4D H4DB 0.9900 . ?
C4D C5D 1.526(2) . ?
C5D H5DA 0.9900 . ?
C5D H5DB 0.9900 . ?
C5D N6D 1.461(2) . ?
N6D H6D 0.8800 . ?
N6D C2D' 1.331(2) . ?
N1D' H1D' 0.8800 . ?
N1D' C2D' 1.359(2) . ?
N1D' C6D' 1.355(2) . ?
C2D' N3D' 1.349(2) . ?
N3D' C4D' 1.330(2) . ?
C4D' H4D' 0.9500 . ?
C4D' C5D' 1.400(2) . ?
C5D' H5D' 0.9500 . ?
C5D' C6D' 1.357(2) . ?
C6D' H6D' 0.9500 . ?
O1C H1C 0.8400 . ?
O1C C2C 1.324(2) . ?
C2C O2C 1.218(2) . ?
C2C C3C 1.510(2) . ?
C3C H3CA 0.9900 . ?
C3C H3CB 0.9900 . ?
C3C C4C 1.522(2) . ?
C4C H4CA 0.9900 . ?
C4C H4CB 0.9900 . ?
C4C C5C 1.530(2) . ?
C5C H5CA 0.9900 . ?
C5C H5CB 0.9900 . ?
C5C N6C 1.460(2) . ?
N6C H6C 0.8800 . ?
N6C C2C' 1.331(2) . ?
N1C' H1C' 0.8800 . ?
N1C' C2C' 1.359(2) . ?
N1C' C6C' 1.353(2) . ?
C2C' N3C' 1.344(2) . ?
N3C' C4C' 1.333(2) . ?
C4C' H4C' 0.9500 . ?
C4C' C5C' 1.397(3) . ?
C5C' H5C' 0.9500 . ?
C5C' C6C' 1.363(2) . ?
C6C' H6C' 0.9500 . ?
O1A H1A 0.8400 . ?
O1A C2A 1.325(2) . ?
C2A O2A 1.2149(19) . ?
C2A C3A 1.501(2) . ?
C3A H3AA 0.9900 . ?
C3A H3AB 0.9900 . ?
C3A C4A 1.521(2) . ?
C4A H4AA 0.9900 . ?
C4A H4AB 0.9900 . ?
C4A C5A 1.525(2) . ?
C5A H5AA 0.9900 . ?
C5A H5AB 0.9900 . ?
C5A N6A 1.461(2) . ?
N6A H6A 0.8800 . ?
N6A C2A' 1.334(2) . ?
N1A' H1A' 0.8800 . ?
N1A' C2A' 1.357(2) . ?
N1A' C6A' 1.348(2) . ?
C2A' N3A' 1.345(2) . ?
N3A' C4A' 1.332(2) . ?
C4A' H4A' 0.9500 . ?
C4A' C5A' 1.394(3) . ?
C5A' H5A' 0.9500 . ?
C5A' C6A' 1.365(3) . ?
C6A' H6A' 0.9500 . ?
N1E O2E 1.2919(18) . ?
N1E O3E 1.2274(18) . ?
N1E O4E 1.2372(18) . ?
N5E O6E 1.2275(19) . ?
N5E O7E 1.2365(19) . ?
N5E O8E 1.2912(19) . ?
N9E O10E 1.2375(19) . ?
N9E O11E 1.2871(19) . ?
N9E O12E 1.2278(18) . ?
N13E O14E 1.2893(18) . ?
N13E O15E 1.2374(18) . ?
N13E O16E 1.2328(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
C2B O1B H1B 109.5 . . ?
O1B C2B C3B 112.76(13) . . ?
O2B C2B O1B 123.22(14) . . ?
O2B C2B C3B 124.02(15) . . ?
C2B C3B H3BA 108.7 . . ?
C2B C3B H3BB 108.7 . . ?
C2B C3B C4B 114.23(13) . . ?
H3BA C3B H3BB 107.6 . . ?
C4B C3B H3BA 108.7 . . ?
C4B C3B H3BB 108.7 . . ?
C3B C4B H4BA 109.4 . . ?
C3B C4B H4BB 109.4 . . ?
C3B C4B C5B 111.08(13) . . ?
H4BA C4B H4BB 108.0 . . ?
C5B C4B H4BA 109.4 . . ?
C5B C4B H4BB 109.4 . . ?
C4B C5B H5BA 109.0 . . ?
C4B C5B H5BB 109.0 . . ?
H5BA C5B H5BB 107.8 . . ?
N6B C5B C4B 112.89(13) . . ?
N6B C5B H5BA 109.0 . . ?
N6B C5B H5BB 109.0 . . ?
C5B N6B H6B 118.8 . . ?
C2B' N6B C5B 122.47(13) . . ?
C2B' N6B H6B 118.8 . . ?
C2B' N1B' H1B' 119.3 . . ?
C2B' N1B' C6B' 121.30(13) . . ?
C6B' N1B' H1B' 119.3 . . ?
N6B C2B' N1B' 118.60(13) . . ?
N6B C2B' N3B' 119.88(14) . . ?
N3B' C2B' N1B' 121.51(14) . . ?
C4B' N3B' C2B' 116.86(14) . . ?
N3B' C4B' H4B' 117.9 . . ?
N3B' C4B' C5B' 124.21(15) . . ?
C5B' C4B' H4B' 117.9 . . ?
C4B' C5B' H5B' 121.5 . . ?
C6B' C5B' C4B' 116.94(15) . . ?
C6B' C5B' H5B' 121.5 . . ?
N1B' C6B' C5B' 119.10(15) . . ?
N1B' C6B' H6B' 120.4 . . ?
C5B' C6B' H6B' 120.4 . . ?
C2D O1D H1D 109.5 . . ?
O1D C2D C3D 112.38(13) . . ?
O2D C2D O1D 123.48(14) . . ?
O2D C2D C3D 124.12(14) . . ?
C2D C3D H3DA 108.7 . . ?
C2D C3D H3DB 108.7 . . ?
C2D C3D C4D 114.36(13) . . ?
H3DA C3D H3DB 107.6 . . ?
C4D C3D H3DA 108.7 . . ?
C4D C3D H3DB 108.7 . . ?
C3D C4D H4DA 109.4 . . ?
C3D C4D H4DB 109.4 . . ?
C3D C4D C5D 111.30(13) . . ?
H4DA C4D H4DB 108.0 . . ?
C5D C4D H4DA 109.4 . . ?
C5D C4D H4DB 109.4 . . ?
C4D C5D H5DA 109.0 . . ?
C4D C5D H5DB 109.0 . . ?
H5DA C5D H5DB 107.8 . . ?
N6D C5D C4D 113.01(13) . . ?
N6D C5D H5DA 109.0 . . ?
N6D C5D H5DB 109.0 . . ?
C5D N6D H6D 118.6 . . ?
C2D' N6D C5D 122.75(13) . . ?
C2D' N6D H6D 118.6 . . ?
C2D' N1D' H1D' 119.4 . . ?
C6D' N1D' H1D' 119.4 . . ?
C6D' N1D' C2D' 121.18(13) . . ?
N6D C2D' N1D' 118.71(14) . . ?
N6D C2D' N3D' 119.99(14) . . ?
N3D' C2D' N1D' 121.29(14) . . ?
C4D' N3D' C2D' 116.96(14) . . ?
N3D' C4D' H4D' 117.9 . . ?
N3D' C4D' C5D' 124.20(15) . . ?
C5D' C4D' H4D' 117.9 . . ?
C4D' C5D' H5D' 121.6 . . ?
C6D' C5D' C4D' 116.75(15) . . ?
C6D' C5D' H5D' 121.6 . . ?
N1D' C6D' C5D' 119.60(15) . . ?
N1D' C6D' H6D' 120.2 . . ?
C5D' C6D' H6D' 120.2 . . ?
C2C O1C H1C 109.5 . . ?
O1C C2C C3C 112.32(13) . . ?
O2C C2C O1C 123.59(14) . . ?
O2C C2C C3C 124.05(15) . . ?
C2C C3C H3CA 108.7 . . ?
C2C C3C H3CB 108.7 . . ?
C2C C3C C4C 114.39(13) . . ?
H3CA C3C H3CB 107.6 . . ?
C4C C3C H3CA 108.7 . . ?
C4C C3C H3CB 108.7 . . ?
C3C C4C H4CA 109.1 . . ?
C3C C4C H4CB 109.1 . . ?
C3C C4C C5C 112.51(13) . . ?
H4CA C4C H4CB 107.8 . . ?
C5C C4C H4CA 109.1 . . ?
C5C C4C H4CB 109.1 . . ?
C4C C5C H5CA 109.2 . . ?
C4C C5C H5CB 109.2 . . ?
H5CA C5C H5CB 107.9 . . ?
N6C C5C C4C 112.14(13) . . ?
N6C C5C H5CA 109.2 . . ?
N6C C5C H5CB 109.2 . . ?
C5C N6C H6C 118.5 . . ?
C2C' N6C C5C 122.92(13) . . ?
C2C' N6C H6C 118.5 . . ?
C2C' N1C' H1C' 119.3 . . ?
C6C' N1C' H1C' 119.3 . . ?
C6C' N1C' C2C' 121.31(14) . . ?
N6C C2C' N1C' 118.48(14) . . ?
N6C C2C' N3C' 120.29(15) . . ?
N3C' C2C' N1C' 121.23(14) . . ?
C4C' N3C' C2C' 117.11(15) . . ?
N3C' C4C' H4C' 117.9 . . ?
N3C' C4C' C5C' 124.21(15) . . ?
C5C' C4C' H4C' 117.9 . . ?
C4C' C5C' H5C' 121.7 . . ?
C6C' C5C' C4C' 116.60(15) . . ?
C6C' C5C' H5C' 121.7 . . ?
N1C' C6C' C5C' 119.54(15) . . ?
N1C' C6C' H6C' 120.2 . . ?
C5C' C6C' H6C' 120.2 . . ?
C2A O1A H1A 109.5 . . ?
O1A C2A C3A 112.53(13) . . ?
O2A C2A O1A 122.82(14) . . ?
O2A C2A C3A 124.65(14) . . ?
C2A C3A H3AA 108.7 . . ?
C2A C3A H3AB 108.7 . . ?
C2A C3A C4A 114.09(12) . . ?
H3AA C3A H3AB 107.6 . . ?
C4A C3A H3AA 108.7 . . ?
C4A C3A H3AB 108.7 . . ?
C3A C4A H4AA 109.4 . . ?
C3A C4A H4AB 109.4 . . ?
C3A C4A C5A 111.03(13) . . ?
H4AA C4A H4AB 108.0 . . ?
C5A C4A H4AA 109.4 . . ?
C5A C4A H4AB 109.4 . . ?
C4A C5A H5AA 108.9 . . ?
C4A C5A H5AB 108.9 . . ?
H5AA C5A H5AB 107.7 . . ?
N6A C5A C4A 113.42(13) . . ?
N6A C5A H5AA 108.9 . . ?
N6A C5A H5AB 108.9 . . ?
C5A N6A H6A 118.9 . . ?
C2A' N6A C5A 122.24(13) . . ?
C2A' N6A H6A 118.9 . . ?
C2A' N1A' H1A' 119.4 . . ?
C6A' N1A' H1A' 119.4 . . ?
C6A' N1A' C2A' 121.23(14) . . ?
N6A C2A' N1A' 118.36(14) . . ?
N6A C2A' N3A' 120.04(14) . . ?
N3A' C2A' N1A' 121.59(14) . . ?
C4A' N3A' C2A' 116.79(15) . . ?
N3A' C4A' H4A' 117.9 . . ?
N3A' C4A' C5A' 124.21(15) . . ?
C5A' C4A' H4A' 117.9 . . ?
C4A' C5A' H5A' 121.6 . . ?
C6A' C5A' C4A' 116.80(15) . . ?
C6A' C5A' H5A' 121.6 . . ?
N1A' C6A' C5A' 119.38(16) . . ?
N1A' C6A' H6A' 120.3 . . ?
C5A' C6A' H6A' 120.3 . . ?
O3E N1E O2E 119.25(13) . . ?
O3E N1E O4E 122.82(14) . . ?
O4E N1E O2E 117.93(13) . . ?
O6E N5E O7E 123.26(14) . . ?
O6E N5E O8E 119.22(13) . . ?
O7E N5E O8E 117.52(13) . . ?
O10E N9E O11E 117.47(13) . . ?
O12E N9E O10E 122.88(14) . . ?
O12E N9E O11E 119.65(13) . . ?
O15E N13E O14E 118.16(13) . . ?
O16E N13E O14E 119.30(13) . . ?
O16E N13E O15E 122.54(14) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O1B H1B O2E 0.84 1.81 2.6511(16) 176.7 . yes
N6B H6B O2C 0.88 2.06 2.8201(17) 144.7 . yes
N1B' H1B' O10E 0.88 2.50 3.1166(18) 127.7 2_656 yes
N1B' H1B' O11E 0.88 1.87 2.7487(18) 175.3 2_656 yes
C6B' H6B' O4E 0.95 2.25 3.107(2) 149.4 1_554 yes
O1D H1D O8E 0.84 1.79 2.6261(17) 177.4 2_657 yes
N6D H6D O2A 0.88 2.07 2.8202(17) 142.1 1_455 yes
N1D' H1D' O14E 0.88 1.92 2.7894(17) 169.0 2_656 yes
N1D' H1D' O15E 0.88 2.48 3.0415(19) 122.2 2_656 yes
C6D' H6D' O7E 0.95 2.36 3.084(2) 133.2 2_656 yes
O1C H1C O11E 0.84 1.83 2.6721(17) 174.8 2_656 yes
N6C H6C O2B 0.88 2.08 2.8266(17) 142.0 . yes
N1C' H1C' O2E 0.88 1.90 2.7701(17) 168.5 . yes
N1C' H1C' O4E 0.88 2.48 3.0683(19) 124.7 . yes
C6C' H6C' O10E 0.95 2.34 3.157(2) 144.3 2_657 yes
O1A H1A O14E 0.84 1.83 2.6707(16) 175.5 2_756 yes
O1A H1A O16E 0.84 2.59 3.1865(18) 128.6 2_756 yes
N6A H6A O2D 0.88 2.10 2.8363(17) 140.3 1_655 yes
N1A' H1A' O7E 0.88 2.51 3.1273(19) 128.0 2_757 yes
N1A' H1A' O8E 0.88 1.85 2.7288(18) 172.6 2_757 yes
C4A' H4A' O1D 0.95 2.46 3.192(2) 133.3 . yes
C6A' H6A' O15E 0.95 2.25 3.112(2) 150.0 2_757 yes

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
O1B C2B C3B C4B 163.36(14) . . . . ?
C2B C3B C4B C5B -67.45(18) . . . . ?
O2B C2B C3B C4B -16.9(2) . . . . ?
C3B C4B C5B N6B -174.92(12) . . . . ?
C4B C5B N6B C2B' 80.10(18) . . . . ?
C5B N6B C2B' N1B' 175.44(14) . . . . ?
C5B N6B C2B' N3B' -3.6(2) . . . . ?
N6B C2B' N3B' C4B' 177.09(14) . . . . ?
N1B' C2B' N3B' C4B' -1.9(2) . . . . ?
C2B' N1B' C6B' C5B' -2.3(2) . . . . ?
C2B' N3B' C4B' C5B' -0.4(2) . . . . ?
N3B' C4B' C5B' C6B' 1.3(2) . . . . ?
C4B' C5B' C6B' N1B' 0.1(2) . . . . ?
C6B' N1B' C2B' N6B -175.71(14) . . . . ?
C6B' N1B' C2B' N3B' 3.3(2) . . . . ?
O1D C2D C3D C4D 174.65(13) . . . . ?
C2D C3D C4D C5D -76.34(17) . . . . ?
O2D C2D C3D C4D -6.9(2) . . . . ?
C3D C4D C5D N6D -177.33(12) . . . . ?
C4D C5D N6D C2D' 78.09(18) . . . . ?
C5D N6D C2D' N1D' -179.88(13) . . . . ?
C5D N6D C2D' N3D' 1.2(2) . . . . ?
N6D C2D' N3D' C4D' 177.91(13) . . . . ?
N1D' C2D' N3D' C4D' -1.0(2) . . . . ?
C2D' N1D' C6D' C5D' -1.1(2) . . . . ?
C2D' N3D' C4D' C5D' 0.2(2) . . . . ?
N3D' C4D' C5D' C6D' 0.1(2) . . . . ?
C4D' C5D' C6D' N1D' 0.4(2) . . . . ?
C6D' N1D' C2D' N6D -177.44(13) . . . . ?
C6D' N1D' C2D' N3D' 1.4(2) . . . . ?
O1C C2C C3C C4C -172.89(13) . . . . ?
C2C C3C C4C C5C 82.17(17) . . . . ?
O2C C2C C3C C4C 9.3(2) . . . . ?
C3C C4C C5C N6C -178.11(12) . . . . ?
C4C C5C N6C C2C' -78.06(18) . . . . ?
C5C N6C C2C' N1C' 177.54(14) . . . . ?
C5C N6C C2C' N3C' -3.4(2) . . . . ?
N6C C2C' N3C' C4C' -179.00(14) . . . . ?
N1C' C2C' N3C' C4C' 0.0(2) . . . . ?
C2C' N1C' C6C' C5C' -1.0(2) . . . . ?
C2C' N3C' C4C' C5C' -0.7(2) . . . . ?
N3C' C4C' C5C' C6C' 0.6(2) . . . . ?
C4C' C5C' C6C' N1C' 0.3(2) . . . . ?
C6C' N1C' C2C' N6C 179.87(13) . . . . ?
C6C' N1C' C2C' N3C' 0.8(2) . . . . ?
O1A C2A C3A C4A -176.08(13) . . . . ?
C2A C3A C4A C5A 73.67(17) . . . . ?
O2A C2A C3A C4A 4.5(2) . . . . ?
C3A C4A C5A N6A 175.91(12) . . . . ?
C4A C5A N6A C2A' -80.82(19) . . . . ?
C5A N6A C2A' N1A' -172.58(14) . . . . ?
C5A N6A C2A' N3A' 6.5(2) . . . . ?
N6A C2A' N3A' C4A' -178.77(14) . . . . ?
N1A' C2A' N3A' C4A' 0.2(2) . . . . ?
C2A' N1A' C6A' C5A' 1.2(2) . . . . ?
C2A' N3A' C4A' C5A' 0.2(2) . . . . ?
N3A' C4A' C5A' C6A' 0.1(3) . . . . ?
C4A' C5A' C6A' N1A' -0.7(2) . . . . ?
C6A' N1A' C2A' N6A 178.10(14) . . . . ?
C6A' N1A' C2A' N3A' -0.9(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_32061802_0m
_database_code_depnum_ccdc_archive 'CCDC 2120748'
loop_
_audit_author_name
_audit_author_address
'Miquel Barcelo-Oliver'
;University of the Balearic Islands
Spain
;
_audit_update_record             
;
2022-11-14 deposited with the CCDC.	2022-11-24 downloaded from the CCDC.
;
_audit_creation_date             2022-11-14
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2019/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C10 H15 N3 O2'
_chemical_formula_sum            'C10 H15 N3 O2'
_chemical_formula_weight         209.25
_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                   6.7614(3)
_cell_length_b                   17.1948(7)
_cell_length_c                   9.2263(4)
_cell_angle_alpha                90
_cell_angle_beta                 102.643(2)
_cell_angle_gamma                90
_cell_volume                     1046.65(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8076
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      28.31
_cell_measurement_theta_min      2.55
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.7172
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS-2016/2 (Bruker AXS Inc.)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.328
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             448
_exptl_crystal_size_max          0.276
_exptl_crystal_size_mid          0.147
_exptl_crystal_size_min          0.085
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0298
_diffrn_reflns_av_unetI/netI     0.0227
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            15512
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.374
_diffrn_reflns_theta_min         2.369
_diffrn_ambient_temperature      173.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker D8 Venture Photon 100 CMOS'
_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                2304
_reflns_number_total             2609
_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       'Bruker SAINT'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_refine_diff_density_max         0.314
_refine_diff_density_min         -0.296
_refine_diff_density_rms         0.052
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     144
_refine_ls_number_reflns         2609
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0430
_refine_ls_R_factor_gt           0.0369
_refine_ls_restrained_S_all      1.048
_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)+(0.0508P)²+0.3666P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0964
_refine_ls_wR_factor_ref         0.1001
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C4(H4A,H4B), C5(H5A,H5B), C6(H6A,H6B), C7(H7A,H7B)
2.b Aromatic/amide H refined with riding coordinates:
 C4'(H4'), C5'(H5'), C6'(H6')
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 1.15126(11) 0.65339(4) 0.39873(8) 0.01627(18) Uani 1 1 d . . . . .
H1 H 1.211(3) 0.6063(11) 0.374(2) 0.048(5) Uiso 1 1 d . . . . .
O2 O 1.37553(13) 0.70713(4) 0.28389(10) 0.0215(2) Uani 1 1 d . . . . .
C2 C 1.24147(15) 0.71378(6) 0.35271(11) 0.0138(2) Uani 1 1 d . . . . .
C3 C 1.17059(16) 0.79232(6) 0.39384(12) 0.0164(2) Uani 1 1 d . . . . .
H3A H 1.140652 0.824980 0.303310 0.020 Uiso 1 1 calc R U . . .
H3B H 1.283697 0.817293 0.464949 0.020 Uiso 1 1 calc R U . . .
C4 C 0.98517(15) 0.79240(6) 0.46190(11) 0.0136(2) Uani 1 1 d . . . . .
H4A H 1.009268 0.756788 0.548295 0.016 Uiso 1 1 calc R U . . .
H4B H 0.867380 0.772422 0.387939 0.016 Uiso 1 1 calc R U . . .
C5 C 0.93496(14) 0.87326(6) 0.51223(11) 0.0132(2) Uani 1 1 d . . . . .
H5A H 1.054335 0.894449 0.583025 0.016 Uiso 1 1 calc R U . . .
H5B H 0.903522 0.908430 0.425263 0.016 Uiso 1 1 calc R U . . .
C6 C 0.75467(15) 0.87045(6) 0.58638(11) 0.0138(2) Uani 1 1 d . . . . .
H6A H 0.634393 0.851323 0.513743 0.017 Uiso 1 1 calc R U . . .
H6B H 0.784032 0.833015 0.669857 0.017 Uiso 1 1 calc R U . . .
C7 C 0.70593(15) 0.94920(6) 0.64469(11) 0.0141(2) Uani 1 1 d . . . . .
H7A H 0.824073 0.968421 0.719268 0.017 Uiso 1 1 calc R U . . .
H7B H 0.675865 0.987166 0.562119 0.017 Uiso 1 1 calc R U . . .
N8 N 0.53111(13) 0.94162(5) 0.71228(10) 0.01434(19) Uani 1 1 d . . . . .
H8 H 0.490(2) 0.8950(9) 0.7303(17) 0.028(4) Uiso 1 1 d . . . . .
N1' N 0.30335(13) 0.98511(5) 0.84659(9) 0.01343(19) Uani 1 1 d . . . . .
C2' C 0.45537(14) 1.00157(6) 0.77622(11) 0.0119(2) Uani 1 1 d . . . . .
N3' N 0.53452(13) 1.07286(5) 0.76508(10) 0.01450(19) Uani 1 1 d . . . . .
C4' C 0.45585(16) 1.13072(6) 0.83068(12) 0.0161(2) Uani 1 1 d . . . . .
H4' H 0.507650 1.181710 0.824805 0.019 Uiso 1 1 calc R U . . .
C5' C 0.30241(16) 1.12034(6) 0.90699(12) 0.0163(2) Uani 1 1 d . . . . .
H5' H 0.249503 1.162322 0.953738 0.020 Uiso 1 1 calc R U . . .
C6' C 0.23118(15) 1.04521(6) 0.91087(11) 0.0156(2) Uani 1 1 d . . . . .
H6' H 0.125656 1.035832 0.961791 0.019 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 H1 0.956(18) . ?
O1 C2 1.3205(12) . ?
O2 C2 1.2206(13) . ?
C2 C3 1.5090(13) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C4 1.5201(14) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C5 1.5273(13) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5 C6 1.5236(13) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C6 C7 1.5196(13) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 N8 1.4580(13) . ?
N8 H8 0.876(16) . ?
N8 C2' 1.3436(13) . ?
N1' C2' 1.3602(13) . ?
N1' C6' 1.3358(13) . ?
C2' N3' 1.3505(13) . ?
N3' C4' 1.3342(13) . ?
C4' H4' 0.9500 . ?
C4' C5' 1.3870(15) . ?
C5' H5' 0.9500 . ?
C5' C6' 1.3820(15) . ?
C6' H6' 0.9500 . ?

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 109.8(11) . . ?
O1 C2 C3 115.36(9) . . ?
O2 C2 O1 122.79(9) . . ?
O2 C2 C3 121.83(9) . . ?
C2 C3 H3A 108.2 . . ?
C2 C3 H3B 108.2 . . ?
C2 C3 C4 116.16(8) . . ?
H3A C3 H3B 107.4 . . ?
C4 C3 H3A 108.2 . . ?
C4 C3 H3B 108.2 . . ?
C3 C4 H4A 109.1 . . ?
C3 C4 H4B 109.1 . . ?
C3 C4 C5 112.63(8) . . ?
H4A C4 H4B 107.8 . . ?
C5 C4 H4A 109.1 . . ?
C5 C4 H4B 109.1 . . ?
C4 C5 H5A 109.4 . . ?
C4 C5 H5B 109.4 . . ?
H5A C5 H5B 108.0 . . ?
C6 C5 C4 111.14(8) . . ?
C6 C5 H5A 109.4 . . ?
C6 C5 H5B 109.4 . . ?
C5 C6 H6A 109.0 . . ?
C5 C6 H6B 109.0 . . ?
H6A C6 H6B 107.8 . . ?
C7 C6 C5 112.81(8) . . ?
C7 C6 H6A 109.0 . . ?
C7 C6 H6B 109.0 . . ?
C6 C7 H7A 109.8 . . ?
C6 C7 H7B 109.8 . . ?
H7A C7 H7B 108.3 . . ?
N8 C7 C6 109.31(8) . . ?
N8 C7 H7A 109.8 . . ?
N8 C7 H7B 109.8 . . ?
C7 N8 H8 118.9(10) . . ?
C2' N8 C7 122.81(8) . . ?
C2' N8 H8 116.8(10) . . ?
C6' N1' C2' 116.02(9) . . ?
N8 C2' N1' 116.78(9) . . ?
N8 C2' N3' 117.87(9) . . ?
N3' C2' N1' 125.35(9) . . ?
C4' N3' C2' 116.00(9) . . ?
N3' C4' H4' 118.3 . . ?
N3' C4' C5' 123.44(9) . . ?
C5' C4' H4' 118.3 . . ?
C4' C5' H5' 122.0 . . ?
C6' C5' C4' 115.92(9) . . ?
C6' C5' H5' 122.0 . . ?
N1' C6' C5' 123.26(10) . . ?
N1' C6' H6' 118.4 . . ?
C5' C6' H6' 118.4 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O1 H1 N1' 0.956(18) 1.729(19) 2.6790(11) 172.1(17) 4_675 yes
N8 H8 O2 0.876(16) 2.024(16) 2.8964(11) 174.0(14) 4_476 yes

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 C2 C3 C4 -8.75(13) . . . . ?
O2 C2 C3 C4 172.48(10) . . . . ?
C2 C3 C4 C5 175.08(9) . . . . ?
C3 C4 C5 C6 -177.31(8) . . . . ?
C4 C5 C6 C7 177.28(8) . . . . ?
C5 C6 C7 N8 179.42(8) . . . . ?
C6 C7 N8 C2' 178.64(9) . . . . ?
C7 N8 C2' N1' -174.36(9) . . . . ?
C7 N8 C2' N3' 5.99(15) . . . . ?
N8 C2' N3' C4' -179.68(9) . . . . ?
N1' C2' N3' C4' 0.70(15) . . . . ?
C2' N1' C6' C5' 0.52(15) . . . . ?
C2' N3' C4' C5' 0.19(15) . . . . ?
N3' C4' C5' C6' -0.63(16) . . . . ?
C4' C5' C6' N1' 0.25(16) . . . . ?
C6' N1' C2' N8 179.33(9) . . . . ?
C6' N1' C2' N3' -1.04(15) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1
_database_code_depnum_ccdc_archive 'CCDC 2120744'
loop_
_audit_author_name
_audit_author_address
'Miquel Barcelo-Oliver'
;University of the Balearic Islands
Spain
;
_audit_update_record             
;
2022-11-16 deposited with the CCDC.	2022-11-24 downloaded from the CCDC.
;
_audit_creation_date             2022-11-16
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2019/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '0.25(C32 H44 N12 O8)'
_chemical_formula_sum            'C8 H11 N3 O2'
_chemical_formula_weight         181.20
_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                   8.1649(7)
_cell_length_b                   40.876(3)
_cell_length_c                   10.4997(8)
_cell_angle_alpha                90
_cell_angle_beta                 92.500(2)
_cell_angle_gamma                90
_cell_volume                     3501.0(5)
_cell_formula_units_Z            16
_cell_measurement_reflns_used    9988
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.36
_cell_measurement_theta_min      2.45
_shelx_estimated_absorpt_T_max   0.988
_shelx_estimated_absorpt_T_min   0.983
_exptl_absorpt_coefficient_mu    0.102
_exptl_absorpt_correction_T_max  0.7335
_exptl_absorpt_correction_T_min  0.7040
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS-2016/2 (Bruker AXS Inc.)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.375
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             1536
_exptl_crystal_size_max          0.169
_exptl_crystal_size_mid          0.138
_exptl_crystal_size_min          0.115
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0519
_diffrn_reflns_av_unetI/netI     0.0333
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       51
_diffrn_reflns_limit_k_min       -51
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            51471
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.442
_diffrn_reflns_theta_min         2.450
_diffrn_ambient_temperature      100.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker D8 Venture Photon 100 CMOS'
_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                5472
_reflns_number_total             7179
_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 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_refine_diff_density_max         0.177
_refine_diff_density_min         -0.271
_refine_diff_density_rms         0.055
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     501
_refine_ls_number_reflns         7179
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0652
_refine_ls_R_factor_gt           0.0416
_refine_ls_restrained_S_all      1.020
_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)+(0.0412P)²+1.5655P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0896
_refine_ls_wR_factor_ref         0.0994
_refine_special_details          ?
_olex2_refinement_description    
;
1.a Secondary CH2 refined with riding coordinates:
 C3A(H3AA,H3AB), C4A(H4AA,H4AB), C5A(H5AA,H5AB), C3C(H3CA,H3CB), C4C(H4CA,
 H4CB), C5C(H5CA,H5CB), C3D(H3DA,H3DB), C4D(H4DA,H4DB), C5D(H5DA,H5DB),
 C3B(H3BA,H3BB), C4B(H4BA,H4BB), C5B(H5BA,H5BB)
1.b Aromatic/amide H refined with riding coordinates:
 C4A'(H4A'), C5A'(H5A'), C6A'(H6A'), C4C'(H4C'), C5C'(H5C'), C6C'(H6C'),
 C4D'(H4D'), C5D'(H5D'), C6D'(H6D'), C4B'(H4B'), C5B'(H5B'), C6B'(H6B')
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1A O 0.70254(13) 0.05396(2) 0.95339(10) 0.0188(2) Uani 1 1 d . . . . .
H1A H 0.648(3) 0.0706(6) 0.883(2) 0.063(7) Uiso 1 1 d . . . . .
O2A O 0.58706(13) 0.01257(2) 0.84194(10) 0.0184(2) Uani 1 1 d . . . . .
C2A C 0.67538(18) 0.02279(4) 0.93009(14) 0.0152(3) Uani 1 1 d . . . . .
C3A C 0.76161(18) 0.00106(3) 1.02643(14) 0.0161(3) Uani 1 1 d . . . . .
H3AA H 0.716001 0.005205 1.110755 0.019 Uiso 1 1 calc R U . . .
H3AB H 0.879025 0.007169 1.032383 0.019 Uiso 1 1 calc R U . . .
C4A C 0.74869(18) -0.03529(3) 0.99794(15) 0.0158(3) Uani 1 1 d . . . . .
H4AA H 0.632518 -0.042228 0.997892 0.019 Uiso 1 1 calc R U . . .
H4AB H 0.790422 -0.039849 0.912616 0.019 Uiso 1 1 calc R U . . .
C5A C 0.84822(18) -0.05420(3) 1.09845(14) 0.0150(3) Uani 1 1 d . . . . .
H5AA H 0.966303 -0.050127 1.087558 0.018 Uiso 1 1 calc R U . . .
H5AB H 0.821026 -0.046221 1.184004 0.018 Uiso 1 1 calc R U . . .
N6A N 0.81696(16) -0.08909(3) 1.09073(13) 0.0158(3) Uani 1 1 d . . . . .
H6A H 0.748(2) -0.0963(4) 1.0353(18) 0.028(5) Uiso 1 1 d . . . . .
N1A' N 0.83807(15) -0.14187(3) 1.16544(12) 0.0157(3) Uani 1 1 d . . . . .
C2A' C 0.88122(18) -0.10994(4) 1.17792(14) 0.0140(3) Uani 1 1 d . . . . .
N3A' N 0.98322(15) -0.09787(3) 1.27179(12) 0.0157(3) Uani 1 1 d . . . . .
C4A' C 1.04179(19) -0.11936(4) 1.35821(15) 0.0183(3) Uani 1 1 d . . . . .
H4A' H 1.113483 -0.111603 1.425225 0.022 Uiso 1 1 calc R U . . .
C5A' C 1.00374(19) -0.15205(4) 1.35516(15) 0.0190(3) Uani 1 1 d . . . . .
H5A' H 1.045893 -0.166925 1.417925 0.023 Uiso 1 1 calc R U . . .
C6A' C 0.89988(19) -0.16198(4) 1.25464(15) 0.0179(3) Uani 1 1 d . . . . .
H6A' H 0.871176 -0.184474 1.249155 0.021 Uiso 1 1 calc R U . . .
O1C O 0.23097(14) 0.19304(2) 0.44157(11) 0.0207(3) Uani 1 1 d . . . . .
H1C H 0.170(3) 0.1781(6) 0.379(2) 0.065(7) Uiso 1 1 d . . . . .
O2C O 0.12742(13) 0.23414(2) 0.32214(10) 0.0186(2) Uani 1 1 d . . . . .
C2C C 0.20819(18) 0.22407(4) 0.41438(14) 0.0148(3) Uani 1 1 d . . . . .
C3C C 0.29182(18) 0.24600(3) 0.51218(14) 0.0151(3) Uani 1 1 d . . . . .
H3CA H 0.406877 0.238720 0.525916 0.018 Uiso 1 1 calc R U . . .
H3CB H 0.237185 0.243418 0.593921 0.018 Uiso 1 1 calc R U . . .
C4C C 0.29129(18) 0.28214(3) 0.47654(14) 0.0144(3) Uani 1 1 d . . . . .
H4CA H 0.346592 0.285302 0.395395 0.017 Uiso 1 1 calc R U . . .
H4CB H 0.177102 0.290109 0.465071 0.017 Uiso 1 1 calc R U . . .
C5C C 0.38065(18) 0.30110(3) 0.58245(14) 0.0145(3) Uani 1 1 d . . . . .
H5CA H 0.326813 0.297032 0.663626 0.017 Uiso 1 1 calc R U . . .
H5CB H 0.494914 0.293085 0.592231 0.017 Uiso 1 1 calc R U . . .
N6C N 0.38236(16) 0.33600(3) 0.55768(12) 0.0163(3) Uani 1 1 d . . . . .
H6C H 0.318(2) 0.3435(4) 0.4942(17) 0.025(5) Uiso 1 1 d . . . . .
N1C' N 0.43611(15) 0.38941(3) 0.61397(12) 0.0163(3) Uani 1 1 d . . . . .
C2C' C 0.45363(17) 0.35717(3) 0.64096(14) 0.0136(3) Uani 1 1 d . . . . .
N3C' N 0.53823(15) 0.34490(3) 0.74390(12) 0.0146(3) Uani 1 1 d . . . . .
C4C' C 0.61006(18) 0.36680(4) 0.82344(14) 0.0170(3) Uani 1 1 d . . . . .
H4C' H 0.670860 0.359009 0.896462 0.020 Uiso 1 1 calc R U . . .
C5C' C 0.59964(18) 0.39999(4) 0.80406(15) 0.0178(3) Uani 1 1 d . . . . .
H5C' H 0.651131 0.415190 0.861344 0.021 Uiso 1 1 calc R U . . .
C6C' C 0.50990(19) 0.40997(4) 0.69637(14) 0.0173(3) Uani 1 1 d . . . . .
H6C' H 0.500327 0.432772 0.680243 0.021 Uiso 1 1 calc R U . . .
O1D O 0.59842(13) 0.28224(3) 0.80684(10) 0.0209(3) Uani 1 1 d . . . . .
H1D H 0.577(3) 0.3053(5) 0.791(2) 0.052(6) Uiso 1 1 d . . . . .
O2D O 0.75605(16) 0.29775(3) 0.97449(12) 0.0343(3) Uani 1 1 d . . . . .
C2D C 0.70329(18) 0.27674(4) 0.90366(14) 0.0161(3) Uani 1 1 d . . . . .
C3D C 0.74675(19) 0.24102(4) 0.91340(14) 0.0162(3) Uani 1 1 d . . . . .
H3DA H 0.818214 0.235385 0.842843 0.019 Uiso 1 1 calc R U . . .
H3DB H 0.645003 0.227983 0.901907 0.019 Uiso 1 1 calc R U . . .
C4D C 0.83305(18) 0.23127(3) 1.03840(14) 0.0149(3) Uani 1 1 d . . . . .
H4DA H 0.767167 0.238409 1.110311 0.018 Uiso 1 1 calc R U . . .
H4DB H 0.941060 0.242249 1.046665 0.018 Uiso 1 1 calc R U . . .
C5D C 0.85668(18) 0.19438(3) 1.04399(14) 0.0148(3) Uani 1 1 d . . . . .
H5DA H 0.748640 0.183465 1.046688 0.018 Uiso 1 1 calc R U . . .
H5DB H 0.910492 0.186860 0.966533 0.018 Uiso 1 1 calc R U . . .
N6D N 0.95667(16) 0.18558(3) 1.15615(13) 0.0167(3) Uani 1 1 d . . . . .
H6D H 1.004(2) 0.2010(4) 1.2044(16) 0.019(4) Uiso 1 1 d . . . . .
N1D' N 0.91993(15) 0.13049(3) 1.11574(12) 0.0158(3) Uani 1 1 d . . . . .
C2D' C 0.98856(17) 0.15432(3) 1.18814(14) 0.0139(3) Uani 1 1 d . . . . .
N3D' N 1.08887(15) 0.14961(3) 1.29310(12) 0.0159(3) Uani 1 1 d . . . . .
C4D' C 1.11894(19) 0.11864(4) 1.32791(15) 0.0175(3) Uani 1 1 d . . . . .
H4D' H 1.188928 0.114485 1.400767 0.021 Uiso 1 1 calc R U . . .
C5D' C 1.05130(19) 0.09264(4) 1.26108(15) 0.0196(3) Uani 1 1 d . . . . .
H5D' H 1.071224 0.070671 1.286919 0.024 Uiso 1 1 calc R U . . .
C6D' C 0.95285(19) 0.10005(4) 1.15441(15) 0.0182(3) Uani 1 1 d . . . . .
H6D' H 0.906144 0.082474 1.106068 0.022 Uiso 1 1 calc R U . . .
O1B O 0.90383(15) 0.03670(3) 0.69347(11) 0.0260(3) Uani 1 1 d . . . . .
H1B H 0.942(3) 0.0598(6) 0.699(2) 0.053(6) Uiso 1 1 d . . . . .
O2B O 0.81568(17) 0.05000(3) 0.49695(12) 0.0360(3) Uani 1 1 d . . . . .
C2B C 0.83485(18) 0.03001(4) 0.58052(14) 0.0159(3) Uani 1 1 d . . . . .
C3B C 0.78734(19) -0.00541(4) 0.57024(14) 0.0167(3) Uani 1 1 d . . . . .
H3BA H 0.712435 -0.010543 0.639141 0.020 Uiso 1 1 calc R U . . .
H3BB H 0.887147 -0.018898 0.584627 0.020 Uiso 1 1 calc R U . . .
C4B C 0.70450(19) -0.01527(4) 0.44356(14) 0.0168(3) Uani 1 1 d . . . . .
H4BA H 0.603791 -0.002139 0.427707 0.020 Uiso 1 1 calc R U . . .
H4BB H 0.779072 -0.010993 0.373585 0.020 Uiso 1 1 calc R U . . .
C5B C 0.66119(19) -0.05137(4) 0.44646(14) 0.0179(3) Uani 1 1 d . . . . .
H5BA H 0.763072 -0.064513 0.452808 0.022 Uiso 1 1 calc R U . . .
H5BB H 0.597707 -0.056010 0.522612 0.022 Uiso 1 1 calc R U . . .
N6B N 0.56530(16) -0.06076(3) 0.33234(13) 0.0174(3) Uani 1 1 d . . . . .
H6B H 0.523(2) -0.0455(4) 0.2850(17) 0.024(5) Uiso 1 1 d . . . . .
N1B' N 0.41953(15) -0.09686(3) 0.20439(12) 0.0157(3) Uani 1 1 d . . . . .
C2B' C 0.51827(18) -0.09180(4) 0.30967(14) 0.0151(3) Uani 1 1 d . . . . .
N3B' N 0.57234(16) -0.11529(3) 0.39082(12) 0.0178(3) Uani 1 1 d . . . . .
C4B' C 0.52070(19) -0.14554(4) 0.36296(15) 0.0195(3) Uani 1 1 d . . . . .
H4B' H 0.555520 -0.162842 0.418141 0.023 Uiso 1 1 calc R U . . .
C5B' C 0.41938(19) -0.15305(4) 0.25825(16) 0.0203(3) Uani 1 1 d . . . . .
H5B' H 0.384348 -0.174830 0.241117 0.024 Uiso 1 1 calc R U . . .
C6B' C 0.37172(19) -0.12752(4) 0.18011(15) 0.0176(3) Uani 1 1 d . . . . .
H6B' H 0.302816 -0.131813 0.106764 0.021 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1A H1A 1.09(2) . ?
O1A C2A 1.3147(17) . ?
O2A C2A 1.2218(18) . ?
C2A C3A 1.499(2) . ?
C3A H3AA 0.9900 . ?
C3A H3AB 0.9900 . ?
C3A C4A 1.518(2) . ?
C4A H4AA 0.9900 . ?
C4A H4AB 0.9900 . ?
C4A C5A 1.516(2) . ?
C5A H5AA 0.9900 . ?
C5A H5AB 0.9900 . ?
C5A N6A 1.4503(18) . ?
N6A H6A 0.843(19) . ?
N6A C2A' 1.3408(19) . ?
N1A' C2A' 1.3567(19) . ?
N1A' C6A' 1.3291(19) . ?
C2A' N3A' 1.3554(19) . ?
N3A' C4A' 1.3364(19) . ?
C4A' H4A' 0.9500 . ?
C4A' C5A' 1.372(2) . ?
C5A' H5A' 0.9500 . ?
C5A' C6A' 1.385(2) . ?
C6A' H6A' 0.9500 . ?
O1C H1C 1.02(2) . ?
O1C C2C 1.3119(18) . ?
O2C C2C 1.2193(18) . ?
C2C C3C 1.504(2) . ?
C3C H3CA 0.9900 . ?
C3C H3CB 0.9900 . ?
C3C C4C 1.5237(19) . ?
C4C H4CA 0.9900 . ?
C4C H4CB 0.9900 . ?
C4C C5C 1.516(2) . ?
C5C H5CA 0.9900 . ?
C5C H5CB 0.9900 . ?
C5C N6C 1.4501(18) . ?
N6C H6C 0.884(18) . ?
N6C C2C' 1.3446(19) . ?
N1C' C2C' 1.3543(19) . ?
N1C' C6C' 1.3313(19) . ?
C2C' N3C' 1.3534(19) . ?
N3C' C4C' 1.3417(19) . ?
C4C' H4C' 0.9500 . ?
C4C' C5C' 1.374(2) . ?
C5C' H5C' 0.9500 . ?
C5C' C6C' 1.382(2) . ?
C6C' H6C' 0.9500 . ?
O1D H1D 0.97(2) . ?
O1D C2D 1.3195(18) . ?
O2D C2D 1.2032(18) . ?
C2D C3D 1.505(2) . ?
C3D H3DA 0.9900 . ?
C3D H3DB 0.9900 . ?
C3D C4D 1.516(2) . ?
C4D H4DA 0.9900 . ?
C4D H4DB 0.9900 . ?
C4D C5D 1.521(2) . ?
C5D H5DA 0.9900 . ?
C5D H5DB 0.9900 . ?
C5D N6D 1.4488(19) . ?
N6D H6D 0.888(18) . ?
N6D C2D' 1.3439(19) . ?
N1D' C2D' 1.3430(19) . ?
N1D' C6D' 1.3323(19) . ?
C2D' N3D' 1.3578(19) . ?
N3D' C4D' 1.3372(19) . ?
C4D' H4D' 0.9500 . ?
C4D' C5D' 1.376(2) . ?
C5D' H5D' 0.9500 . ?
C5D' C6D' 1.383(2) . ?
C6D' H6D' 0.9500 . ?
O1B H1B 0.99(2) . ?
O1B C2B 1.3192(18) . ?
O2B C2B 1.2041(19) . ?
C2B C3B 1.502(2) . ?
C3B H3BA 0.9900 . ?
C3B H3BB 0.9900 . ?
C3B C4B 1.520(2) . ?
C4B H4BA 0.9900 . ?
C4B H4BB 0.9900 . ?
C4B C5B 1.518(2) . ?
C5B H5BA 0.9900 . ?
C5B H5BB 0.9900 . ?
C5B N6B 1.4540(19) . ?
N6B H6B 0.860(18) . ?
N6B C2B' 1.3440(19) . ?
N1B' C2B' 1.3553(19) . ?
N1B' C6B' 1.3340(19) . ?
C2B' N3B' 1.3453(19) . ?
N3B' C4B' 1.335(2) . ?
C4B' H4B' 0.9500 . ?
C4B' C5B' 1.381(2) . ?
C5B' H5B' 0.9500 . ?
C5B' C6B' 1.373(2) . ?
C6B' H6B' 0.9500 . ?

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
C2A O1A H1A 114.6(12) . . ?
O1A C2A C3A 112.23(13) . . ?
O2A C2A O1A 124.17(14) . . ?
O2A C2A C3A 123.58(13) . . ?
C2A C3A H3AA 108.6 . . ?
C2A C3A H3AB 108.6 . . ?
C2A C3A C4A 114.86(12) . . ?
H3AA C3A H3AB 107.5 . . ?
C4A C3A H3AA 108.6 . . ?
C4A C3A H3AB 108.6 . . ?
C3A C4A H4AA 109.8 . . ?
C3A C4A H4AB 109.8 . . ?
H4AA C4A H4AB 108.3 . . ?
C5A C4A C3A 109.36(12) . . ?
C5A C4A H4AA 109.8 . . ?
C5A C4A H4AB 109.8 . . ?
C4A C5A H5AA 109.2 . . ?
C4A C5A H5AB 109.2 . . ?
H5AA C5A H5AB 107.9 . . ?
N6A C5A C4A 112.02(12) . . ?
N6A C5A H5AA 109.2 . . ?
N6A C5A H5AB 109.2 . . ?
C5A N6A H6A 119.4(12) . . ?
C2A' N6A C5A 121.61(13) . . ?
C2A' N6A H6A 118.6(12) . . ?
C6A' N1A' C2A' 115.97(13) . . ?
N6A C2A' N1A' 116.96(13) . . ?
N6A C2A' N3A' 118.35(13) . . ?
N3A' C2A' N1A' 124.69(13) . . ?
C4A' N3A' C2A' 116.41(13) . . ?
N3A' C4A' H4A' 118.3 . . ?
N3A' C4A' C5A' 123.40(15) . . ?
C5A' C4A' H4A' 118.3 . . ?
C4A' C5A' H5A' 122.2 . . ?
C4A' C5A' C6A' 115.69(14) . . ?
C6A' C5A' H5A' 122.2 . . ?
N1A' C6A' C5A' 123.82(14) . . ?
N1A' C6A' H6A' 118.1 . . ?
C5A' C6A' H6A' 118.1 . . ?
C2C O1C H1C 112.4(13) . . ?
O1C C2C C3C 111.83(13) . . ?
O2C C2C O1C 124.46(14) . . ?
O2C C2C C3C 123.70(13) . . ?
C2C C3C H3CA 108.7 . . ?
C2C C3C H3CB 108.7 . . ?
C2C C3C C4C 114.43(12) . . ?
H3CA C3C H3CB 107.6 . . ?
C4C C3C H3CA 108.7 . . ?
C4C C3C H3CB 108.7 . . ?
C3C C4C H4CA 110.0 . . ?
C3C C4C H4CB 110.0 . . ?
H4CA C4C H4CB 108.3 . . ?
C5C C4C C3C 108.63(12) . . ?
C5C C4C H4CA 110.0 . . ?
C5C C4C H4CB 110.0 . . ?
C4C C5C H5CA 109.1 . . ?
C4C C5C H5CB 109.1 . . ?
H5CA C5C H5CB 107.9 . . ?
N6C C5C C4C 112.30(12) . . ?
N6C C5C H5CA 109.1 . . ?
N6C C5C H5CB 109.1 . . ?
C5C N6C H6C 117.7(11) . . ?
C2C' N6C C5C 121.58(13) . . ?
C2C' N6C H6C 119.6(11) . . ?
C6C' N1C' C2C' 115.95(13) . . ?
N6C C2C' N1C' 116.84(13) . . ?
N6C C2C' N3C' 118.18(13) . . ?
N3C' C2C' N1C' 124.98(13) . . ?
C4C' N3C' C2C' 116.35(13) . . ?
N3C' C4C' H4C' 118.5 . . ?
N3C' C4C' C5C' 122.96(14) . . ?
C5C' C4C' H4C' 118.5 . . ?
C4C' C5C' H5C' 122.0 . . ?
C4C' C5C' C6C' 116.10(14) . . ?
C6C' C5C' H5C' 122.0 . . ?
N1C' C6C' C5C' 123.66(14) . . ?
N1C' C6C' H6C' 118.2 . . ?
C5C' C6C' H6C' 118.2 . . ?
C2D O1D H1D 114.0(13) . . ?
O1D C2D C3D 111.14(13) . . ?
O2D C2D O1D 123.89(14) . . ?
O2D C2D C3D 124.97(14) . . ?
C2D C3D H3DA 108.7 . . ?
C2D C3D H3DB 108.7 . . ?
C2D C3D C4D 114.42(13) . . ?
H3DA C3D H3DB 107.6 . . ?
C4D C3D H3DA 108.7 . . ?
C4D C3D H3DB 108.7 . . ?
C3D C4D H4DA 109.6 . . ?
C3D C4D H4DB 109.6 . . ?
C3D C4D C5D 110.34(12) . . ?
H4DA C4D H4DB 108.1 . . ?
C5D C4D H4DA 109.6 . . ?
C5D C4D H4DB 109.6 . . ?
C4D C5D H5DA 109.6 . . ?
C4D C5D H5DB 109.6 . . ?
H5DA C5D H5DB 108.2 . . ?
N6D C5D C4D 110.08(12) . . ?
N6D C5D H5DA 109.6 . . ?
N6D C5D H5DB 109.6 . . ?
C5D N6D H6D 120.2(11) . . ?
C2D' N6D C5D 122.36(13) . . ?
C2D' N6D H6D 117.4(11) . . ?
C6D' N1D' C2D' 115.54(13) . . ?
N6D C2D' N3D' 116.18(13) . . ?
N1D' C2D' N6D 118.48(13) . . ?
N1D' C2D' N3D' 125.35(13) . . ?
C4D' N3D' C2D' 116.95(13) . . ?
N3D' C4D' H4D' 119.1 . . ?
N3D' C4D' C5D' 121.80(14) . . ?
C5D' C4D' H4D' 119.1 . . ?
C4D' C5D' H5D' 121.6 . . ?
C4D' C5D' C6D' 116.72(14) . . ?
C6D' C5D' H5D' 121.6 . . ?
N1D' C6D' C5D' 123.62(14) . . ?
N1D' C6D' H6D' 118.2 . . ?
C5D' C6D' H6D' 118.2 . . ?
C2B O1B H1B 111.8(13) . . ?
O1B C2B C3B 111.31(13) . . ?
O2B C2B O1B 123.45(14) . . ?
O2B C2B C3B 125.23(14) . . ?
C2B C3B H3BA 108.5 . . ?
C2B C3B H3BB 108.5 . . ?
C2B C3B C4B 114.98(13) . . ?
H3BA C3B H3BB 107.5 . . ?
C4B C3B H3BA 108.5 . . ?
C4B C3B H3BB 108.5 . . ?
C3B C4B H4BA 109.8 . . ?
C3B C4B H4BB 109.8 . . ?
H4BA C4B H4BB 108.2 . . ?
C5B C4B C3B 109.60(12) . . ?
C5B C4B H4BA 109.8 . . ?
C5B C4B H4BB 109.8 . . ?
C4B C5B H5BA 109.5 . . ?
C4B C5B H5BB 109.5 . . ?
H5BA C5B H5BB 108.0 . . ?
N6B C5B C4B 110.94(12) . . ?
N6B C5B H5BA 109.5 . . ?
N6B C5B H5BB 109.5 . . ?
C5B N6B H6B 118.1(12) . . ?
C2B' N6B C5B 122.31(13) . . ?
C2B' N6B H6B 118.7(12) . . ?
C6B' N1B' C2B' 117.25(13) . . ?
N6B C2B' N1B' 116.34(13) . . ?
N6B C2B' N3B' 118.57(14) . . ?
N3B' C2B' N1B' 125.09(13) . . ?
C4B' N3B' C2B' 115.50(13) . . ?
N3B' C4B' H4B' 118.2 . . ?
N3B' C4B' C5B' 123.56(14) . . ?
C5B' C4B' H4B' 118.2 . . ?
C4B' C5B' H5B' 121.6 . . ?
C6B' C5B' C4B' 116.81(14) . . ?
C6B' C5B' H5B' 121.6 . . ?
N1B' C6B' C5B' 121.79(15) . . ?
N1B' C6B' H6B' 119.1 . . ?
C5B' C6B' H6B' 119.1 . . ?

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
O1A C2A C3A C4A -174.40(12) . . . . ?
O2A C2A C3A C4A 7.2(2) . . . . ?
C2A C3A C4A C5A 177.01(12) . . . . ?
C3A C4A C5A N6A 169.30(12) . . . . ?
C4A C5A N6A C2A' -173.95(13) . . . . ?
C5A N6A C2A' N1A' 176.90(13) . . . . ?
C5A N6A C2A' N3A' -2.9(2) . . . . ?
N6A C2A' N3A' C4A' 178.63(13) . . . . ?
N1A' C2A' N3A' C4A' -1.1(2) . . . . ?
C2A' N1A' C6A' C5A' -0.6(2) . . . . ?
C2A' N3A' C4A' C5A' 0.1(2) . . . . ?
N3A' C4A' C5A' C6A' 0.6(2) . . . . ?
C4A' C5A' C6A' N1A' -0.3(2) . . . . ?
C6A' N1A' C2A' N6A -178.39(13) . . . . ?
C6A' N1A' C2A' N3A' 1.4(2) . . . . ?
O1C C2C C3C C4C 171.54(12) . . . . ?
O2C C2C C3C C4C -9.3(2) . . . . ?
C2C C3C C4C C5C -179.41(12) . . . . ?
C3C C4C C5C N6C -178.55(12) . . . . ?
C4C C5C N6C C2C' 179.07(13) . . . . ?
C5C N6C C2C' N1C' -174.45(13) . . . . ?
C5C N6C C2C' N3C' 6.2(2) . . . . ?
N6C C2C' N3C' C4C' 178.80(13) . . . . ?
N1C' C2C' N3C' C4C' -0.5(2) . . . . ?
C2C' N1C' C6C' C5C' -0.1(2) . . . . ?
C2C' N3C' C4C' C5C' 0.3(2) . . . . ?
N3C' C4C' C5C' C6C' -0.1(2) . . . . ?
C4C' C5C' C6C' N1C' 0.0(2) . . . . ?
C6C' N1C' C2C' N6C -178.88(13) . . . . ?
C6C' N1C' C2C' N3C' 0.4(2) . . . . ?
O1D C2D C3D C4D -166.08(13) . . . . ?
O2D C2D C3D C4D 13.7(2) . . . . ?
C2D C3D C4D C5D 174.51(13) . . . . ?
C3D C4D C5D N6D 172.98(12) . . . . ?
C4D C5D N6D C2D' 176.04(13) . . . . ?
C5D N6D C2D' N1D' -2.5(2) . . . . ?
C5D N6D C2D' N3D' 177.69(13) . . . . ?
N6D C2D' N3D' C4D' 178.56(13) . . . . ?
N1D' C2D' N3D' C4D' -1.2(2) . . . . ?
C2D' N1D' C6D' C5D' -0.3(2) . . . . ?
C2D' N3D' C4D' C5D' -0.2(2) . . . . ?
N3D' C4D' C5D' C6D' 1.2(2) . . . . ?
C4D' C5D' C6D' N1D' -0.9(2) . . . . ?
C6D' N1D' C2D' N6D -178.30(14) . . . . ?
C6D' N1D' C2D' N3D' 1.5(2) . . . . ?
O1B C2B C3B C4B 179.17(13) . . . . ?
O2B C2B C3B C4B -1.8(2) . . . . ?
C2B C3B C4B C5B -179.28(13) . . . . ?
C3B C4B C5B N6B 173.53(13) . . . . ?
C4B C5B N6B C2B' 176.89(14) . . . . ?
C5B N6B C2B' N1B' 175.42(13) . . . . ?
C5B N6B C2B' N3B' -5.1(2) . . . . ?
N6B C2B' N3B' C4B' 179.82(14) . . . . ?
N1B' C2B' N3B' C4B' -0.7(2) . . . . ?
C2B' N1B' C6B' C5B' 0.3(2) . . . . ?
C2B' N3B' C4B' C5B' 0.4(2) . . . . ?
N3B' C4B' C5B' C6B' 0.2(2) . . . . ?
C4B' C5B' C6B' N1B' -0.6(2) . . . . ?
C6B' N1B' C2B' N6B 179.89(13) . . . . ?
C6B' N1B' C2B' N3B' 0.4(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1_a_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2120749'
loop_
_audit_author_name
_audit_author_address
'Miquel Barcelo-Oliver'
;University of the Balearic Islands
Spain
;
_audit_update_record             
;
2022-11-15 deposited with the CCDC.	2022-11-24 downloaded from the CCDC.
;
_audit_creation_date             2022-11-15
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2019/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C10 H16 N3 O2, N O3, H2 O'
_chemical_formula_sum            'C10 H18 N4 O6'
_chemical_formula_weight         290.28
_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 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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                   9.9111(9)
_cell_length_b                   10.2045(9)
_cell_length_c                   15.5393(14)
_cell_angle_alpha                81.938(4)
_cell_angle_beta                 74.159(4)
_cell_angle_gamma                62.779(3)
_cell_volume                     1344.3(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9600
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      68.23
_cell_measurement_theta_min      2.96
_shelx_estimated_absorpt_T_max   0.763
_shelx_estimated_absorpt_T_min   0.674
_exptl_absorpt_coefficient_mu    1.020
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.5539
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1511 before and 0.0842 after correction.
The Ratio of minimum to maximum transmission is 0.7355.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.434
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             616
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.28
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0535
_diffrn_reflns_av_unetI/netI     0.0222
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            91370
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.497
_diffrn_reflns_theta_min         2.956
_diffrn_ambient_temperature      100.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4786
_reflns_number_total             4906
_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       'Bruker Apex3, 2016'
_computing_data_collection       'Bruker Apex3, 2016'
_computing_data_reduction        'SAINT v8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.274
_refine_diff_density_min         -0.238
_refine_diff_density_rms         0.051
_refine_ls_extinction_coef       0.0033(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2019/1 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     370
_refine_ls_number_reflns         4906
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0367
_refine_ls_R_factor_gt           0.0362
_refine_ls_restrained_S_all      1.076
_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)+(0.0537P)²+0.4833P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0996
_refine_ls_wR_factor_ref         0.1001
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All O(H) groups, All O(H,H) groups
2.a Free rotating group:
 O1W(H1WA,H1WB), O2W(H2WA,H2WB)
2.b Secondary CH2 refined with riding coordinates:
 C3A(H3AA,H3AB), C4A(H4AA,H4AB), C5A(H5AA,H5AB), C6A(H6AA,H6AB), C7A(H7AB,
 H7AA), C3B(H3BA,H3BB), C4B(H4BA,H4BB), C5B(H5BA,H5BB), C6B(H6BA,H6BB),
 C7B(H7BA,H7BB)
2.c Aromatic/amide H refined with riding coordinates:
 N8A(H8A), N1A'(H1A'), C4A'(H4A'), C5A'(H5A'), C6A'(H6A'), N8B(H8B),
 N1B'(H1B'), C4B'(H4B'), C5B'(H5B'), C6B'(H6B')
2.d Idealised tetrahedral OH refined as rotating group:
 O1A(H1A), O1B(H1B)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1A O 0.58841(11) 0.59047(10) 0.41981(6) 0.0293(2) Uani 1 1 d . . . . .
H1A H 0.582960 0.564487 0.372397 0.044 Uiso 1 1 calc R U . . .
C2A C 0.70710(14) 0.48447(13) 0.44852(8) 0.0187(3) Uani 1 1 d . . . . .
O2A O 0.79111(11) 0.36821(10) 0.41062(6) 0.0274(2) Uani 1 1 d . . . . .
C3A C 0.72754(14) 0.52507(13) 0.53211(8) 0.0204(3) Uani 1 1 d . . . . .
H3AA H 0.631193 0.545113 0.579785 0.024 Uiso 1 1 calc R U . . .
H3AB H 0.739580 0.617498 0.520042 0.024 Uiso 1 1 calc R U . . .
C4A C 0.86590(14) 0.40894(13) 0.56669(8) 0.0205(3) Uani 1 1 d . . . . .
H4AA H 0.961232 0.379372 0.517351 0.025 Uiso 1 1 calc R U . . .
H4AB H 0.847883 0.320651 0.587045 0.025 Uiso 1 1 calc R U . . .
C5A C 0.89127(14) 0.46544(13) 0.64395(8) 0.0195(3) Uani 1 1 d . . . . .
H5AA H 0.906996 0.554994 0.623974 0.023 Uiso 1 1 calc R U . . .
H5AB H 0.796785 0.492983 0.693795 0.023 Uiso 1 1 calc R U . . .
C6A C 1.03201(14) 0.35025(13) 0.67733(8) 0.0194(3) Uani 1 1 d . . . . .
H6AA H 1.016041 0.260832 0.697368 0.023 Uiso 1 1 calc R U . . .
H6AB H 1.126308 0.322475 0.627346 0.023 Uiso 1 1 calc R U . . .
C7A C 1.05861(14) 0.40560(13) 0.75412(8) 0.0194(3) Uani 1 1 d . . . . .
H7AB H 1.074161 0.495362 0.734684 0.023 Uiso 1 1 calc R U . . .
H7AA H 0.965632 0.431606 0.804887 0.023 Uiso 1 1 calc R U . . .
N8A N 1.19591(12) 0.29188(11) 0.78284(7) 0.0194(2) Uani 1 1 d . . . . .
H8A H 1.243255 0.205672 0.756952 0.023 Uiso 1 1 calc R U . . .
N1A' N 1.18213(11) 0.43919(10) 0.88945(6) 0.0177(2) Uani 1 1 d . . . . .
H1A' H 1.096211 0.510359 0.877048 0.021 Uiso 1 1 calc R U . . .
C2A' C 1.25358(13) 0.31013(13) 0.84516(8) 0.0176(2) Uani 1 1 d . . . . .
N3A' N 1.38380(12) 0.19743(11) 0.86437(7) 0.0204(2) Uani 1 1 d . . . . .
C4A' C 1.44051(14) 0.21859(14) 0.92621(8) 0.0220(3) Uani 1 1 d . . . . .
H4A' H 1.532264 0.140126 0.939654 0.026 Uiso 1 1 calc R U . . .
C5A' C 1.37305(14) 0.35008(14) 0.97303(8) 0.0222(3) Uani 1 1 d . . . . .
H5A' H 1.417055 0.361939 1.016875 0.027 Uiso 1 1 calc R U . . .
C6A' C 1.24154(14) 0.45968(13) 0.95251(8) 0.0195(3) Uani 1 1 d . . . . .
H6A' H 1.191076 0.550961 0.982447 0.023 Uiso 1 1 calc R U . . .
O1B O 0.55020(10) 0.82294(9) 0.65907(6) 0.0242(2) Uani 1 1 d . . . . .
H1B H 0.555603 0.848637 0.706591 0.036 Uiso 1 1 calc R U . . .
C2B C 0.42137(13) 0.92124(12) 0.63609(8) 0.0182(2) Uani 1 1 d . . . . .
O2B O 0.32851(10) 1.03183(9) 0.67843(6) 0.0252(2) Uani 1 1 d . . . . .
C3B C 0.40003(14) 0.88056(13) 0.55288(8) 0.0197(3) Uani 1 1 d . . . . .
H3BA H 0.381399 0.791641 0.566249 0.024 Uiso 1 1 calc R U . . .
H3BB H 0.498282 0.854612 0.505993 0.024 Uiso 1 1 calc R U . . .
C4B C 0.26669(14) 1.00075(13) 0.51589(8) 0.0188(3) Uani 1 1 d . . . . .
H4BA H 0.283681 1.090562 0.502600 0.023 Uiso 1 1 calc R U . . .
H4BB H 0.167215 1.025518 0.561572 0.023 Uiso 1 1 calc R U . . .
C5B C 0.25488(14) 0.95186(13) 0.43082(8) 0.0192(3) Uani 1 1 d . . . . .
H5BA H 0.353471 0.929596 0.384716 0.023 Uiso 1 1 calc R U . . .
H5BB H 0.241064 0.860375 0.443826 0.023 Uiso 1 1 calc R U . . .
C6B C 0.11886(14) 1.06973(13) 0.39438(8) 0.0194(3) Uani 1 1 d . . . . .
H6BA H 0.021401 1.097637 0.442073 0.023 Uiso 1 1 calc R U . . .
H6BB H 0.136858 1.158590 0.376950 0.023 Uiso 1 1 calc R U . . .
C7B C 0.09926(13) 1.01692(12) 0.31403(8) 0.0182(2) Uani 1 1 d . . . . .
H7BA H 0.190878 1.000872 0.263410 0.022 Uiso 1 1 calc R U . . .
H7BB H 0.093108 0.921956 0.329008 0.022 Uiso 1 1 calc R U . . .
N8B N -0.04303(12) 1.12629(11) 0.28798(7) 0.0185(2) Uani 1 1 d . . . . .
H8B H -0.097479 1.208946 0.317830 0.022 Uiso 1 1 calc R U . . .
N1B' N -0.01543(11) 0.98410(10) 0.17401(6) 0.0167(2) Uani 1 1 d . . . . .
H1B' H 0.073622 0.916021 0.184533 0.020 Uiso 1 1 calc R U . . .
C2B' C -0.09520(13) 1.10923(12) 0.22266(8) 0.0167(2) Uani 1 1 d . . . . .
N3B' N -0.22921(12) 1.21879(11) 0.20509(7) 0.0189(2) Uani 1 1 d . . . . .
C4B' C -0.28199(14) 1.19727(13) 0.14139(8) 0.0204(3) Uani 1 1 d . . . . .
H4B' H -0.375847 1.273518 0.128895 0.024 Uiso 1 1 calc R U . . .
C5B' C -0.20752(14) 1.06870(13) 0.09137(8) 0.0208(3) Uani 1 1 d . . . . .
H5B' H -0.249818 1.055829 0.046976 0.025 Uiso 1 1 calc R U . . .
C6B' C -0.07167(14) 0.96314(13) 0.10944(8) 0.0188(3) Uani 1 1 d . . . . .
H6B' H -0.015934 0.874355 0.076724 0.023 Uiso 1 1 calc R U . . .
N1C N 0.29940(11) 0.64295(11) 0.14023(7) 0.0191(2) Uani 1 1 d . . . . .
O2C O 0.26448(10) 0.73815(10) 0.19699(6) 0.0250(2) Uani 1 1 d . . . . .
O3C O 0.23765(11) 0.68080(10) 0.07567(7) 0.0330(2) Uani 1 1 d . . . . .
O4C O 0.39565(10) 0.51386(9) 0.15000(6) 0.0279(2) Uani 1 1 d . . . . .
N5C N 0.87006(11) 0.78395(11) 0.91573(7) 0.0181(2) Uani 1 1 d . . . . .
O6C O 0.75581(10) 0.90600(9) 0.91175(6) 0.0256(2) Uani 1 1 d . . . . .
O7C O 0.90635(10) 0.68500(9) 0.86183(6) 0.0248(2) Uani 1 1 d . . . . .
O8C O 0.94828(10) 0.75968(10) 0.97155(6) 0.0253(2) Uani 1 1 d . . . . .
O1W O 0.56748(11) 0.51342(10) 0.27339(6) 0.0266(2) Uani 1 1 d G . . . .
H1WA H 0.490274 0.541765 0.247899 0.040 Uiso 1 1 d G U . . .
H1WB H 0.626908 0.422274 0.257537 0.040 Uiso 1 1 d G U . . .
O2W O 0.56251(11) 0.89305(10) 0.80989(6) 0.0282(2) Uani 1 1 d G . . . .
H2WA H 0.505120 0.986332 0.821050 0.042 Uiso 1 1 d G U . . .
H2WB H 0.643240 0.869628 0.831396 0.042 Uiso 1 1 d G 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
O1A H1A 0.8400 . ?
O1A C2A 1.3191(15) . ?
C2A O2A 1.2132(15) . ?
C2A C3A 1.5071(16) . ?
C3A H3AA 0.9900 . ?
C3A H3AB 0.9900 . ?
C3A C4A 1.5200(16) . ?
C4A H4AA 0.9900 . ?
C4A H4AB 0.9900 . ?
C4A C5A 1.5261(16) . ?
C5A H5AA 0.9900 . ?
C5A H5AB 0.9900 . ?
C5A C6A 1.5232(16) . ?
C6A H6AA 0.9900 . ?
C6A H6AB 0.9900 . ?
C6A C7A 1.5198(16) . ?
C7A H7AB 0.9900 . ?
C7A H7AA 0.9900 . ?
C7A N8A 1.4626(15) . ?
N8A H8A 0.8800 . ?
N8A C2A' 1.3227(16) . ?
N1A' H1A' 0.8800 . ?
N1A' C2A' 1.3581(15) . ?
N1A' C6A' 1.3548(16) . ?
C2A' N3A' 1.3540(16) . ?
N3A' C4A' 1.3229(16) . ?
C4A' H4A' 0.9500 . ?
C4A' C5A' 1.4016(17) . ?
C5A' H5A' 0.9500 . ?
C5A' C6A' 1.3582(17) . ?
C6A' H6A' 0.9500 . ?
O1B H1B 0.8400 . ?
O1B C2B 1.3194(14) . ?
C2B O2B 1.2169(14) . ?
C2B C3B 1.5064(16) . ?
C3B H3BA 0.9900 . ?
C3B H3BB 0.9900 . ?
C3B C4B 1.5216(16) . ?
C4B H4BA 0.9900 . ?
C4B H4BB 0.9900 . ?
C4B C5B 1.5273(16) . ?
C5B H5BA 0.9900 . ?
C5B H5BB 0.9900 . ?
C5B C6B 1.5255(16) . ?
C6B H6BA 0.9900 . ?
C6B H6BB 0.9900 . ?
C6B C7B 1.5179(16) . ?
C7B H7BA 0.9900 . ?
C7B H7BB 0.9900 . ?
C7B N8B 1.4640(15) . ?
N8B H8B 0.8800 . ?
N8B C2B' 1.3216(16) . ?
N1B' H1B' 0.8800 . ?
N1B' C2B' 1.3593(15) . ?
N1B' C6B' 1.3556(15) . ?
C2B' N3B' 1.3574(15) . ?
N3B' C4B' 1.3230(16) . ?
C4B' H4B' 0.9500 . ?
C4B' C5B' 1.3990(17) . ?
C5B' H5B' 0.9500 . ?
C5B' C6B' 1.3590(17) . ?
C6B' H6B' 0.9500 . ?
N1C O2C 1.2679(13) . ?
N1C O3C 1.2412(14) . ?
N1C O4C 1.2416(13) . ?
N5C O6C 1.2504(13) . ?
N5C O7C 1.2613(13) . ?
N5C O8C 1.2434(13) . ?
O1W H1WA 0.8700 . ?
O1W H1WB 0.8698 . ?
O2W H2WA 0.8700 . ?
O2W H2WB 0.8704 . ?

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
C2A O1A H1A 109.5 . . ?
O1A C2A C3A 112.57(10) . . ?
O2A C2A O1A 123.23(11) . . ?
O2A C2A C3A 124.19(11) . . ?
C2A C3A H3AA 108.5 . . ?
C2A C3A H3AB 108.5 . . ?
C2A C3A C4A 114.94(10) . . ?
H3AA C3A H3AB 107.5 . . ?
C4A C3A H3AA 108.5 . . ?
C4A C3A H3AB 108.5 . . ?
C3A C4A H4AA 109.3 . . ?
C3A C4A H4AB 109.3 . . ?
C3A C4A C5A 111.82(9) . . ?
H4AA C4A H4AB 107.9 . . ?
C5A C4A H4AA 109.3 . . ?
C5A C4A H4AB 109.3 . . ?
C4A C5A H5AA 109.2 . . ?
C4A C5A H5AB 109.2 . . ?
H5AA C5A H5AB 107.9 . . ?
C6A C5A C4A 111.85(9) . . ?
C6A C5A H5AA 109.2 . . ?
C6A C5A H5AB 109.2 . . ?
C5A C6A H6AA 109.2 . . ?
C5A C6A H6AB 109.2 . . ?
H6AA C6A H6AB 107.9 . . ?
C7A C6A C5A 112.27(9) . . ?
C7A C6A H6AA 109.2 . . ?
C7A C6A H6AB 109.2 . . ?
C6A C7A H7AB 109.6 . . ?
C6A C7A H7AA 109.6 . . ?
H7AB C7A H7AA 108.2 . . ?
N8A C7A C6A 110.10(9) . . ?
N8A C7A H7AB 109.6 . . ?
N8A C7A H7AA 109.6 . . ?
C7A N8A H8A 117.9 . . ?
C2A' N8A C7A 124.28(10) . . ?
C2A' N8A H8A 117.9 . . ?
C2A' N1A' H1A' 119.6 . . ?
C6A' N1A' H1A' 119.6 . . ?
C6A' N1A' C2A' 120.80(10) . . ?
N8A C2A' N1A' 120.37(10) . . ?
N8A C2A' N3A' 118.74(10) . . ?
N3A' C2A' N1A' 120.89(10) . . ?
C4A' N3A' C2A' 117.75(10) . . ?
N3A' C4A' H4A' 118.1 . . ?
N3A' C4A' C5A' 123.80(11) . . ?
C5A' C4A' H4A' 118.1 . . ?
C4A' C5A' H5A' 121.7 . . ?
C6A' C5A' C4A' 116.57(11) . . ?
C6A' C5A' H5A' 121.7 . . ?
N1A' C6A' C5A' 120.18(11) . . ?
N1A' C6A' H6A' 119.9 . . ?
C5A' C6A' H6A' 119.9 . . ?
C2B O1B H1B 109.5 . . ?
O1B C2B C3B 112.82(10) . . ?
O2B C2B O1B 123.54(11) . . ?
O2B C2B C3B 123.62(11) . . ?
C2B C3B H3BA 108.6 . . ?
C2B C3B H3BB 108.6 . . ?
C2B C3B C4B 114.67(9) . . ?
H3BA C3B H3BB 107.6 . . ?
C4B C3B H3BA 108.6 . . ?
C4B C3B H3BB 108.6 . . ?
C3B C4B H4BA 109.4 . . ?
C3B C4B H4BB 109.4 . . ?
C3B C4B C5B 111.37(9) . . ?
H4BA C4B H4BB 108.0 . . ?
C5B C4B H4BA 109.4 . . ?
C5B C4B H4BB 109.4 . . ?
C4B C5B H5BA 109.2 . . ?
C4B C5B H5BB 109.2 . . ?
H5BA C5B H5BB 107.9 . . ?
C6B C5B C4B 111.95(9) . . ?
C6B C5B H5BA 109.2 . . ?
C6B C5B H5BB 109.2 . . ?
C5B C6B H6BA 109.2 . . ?
C5B C6B H6BB 109.2 . . ?
H6BA C6B H6BB 107.9 . . ?
C7B C6B C5B 112.01(9) . . ?
C7B C6B H6BA 109.2 . . ?
C7B C6B H6BB 109.2 . . ?
C6B C7B H7BA 109.6 . . ?
C6B C7B H7BB 109.6 . . ?
H7BA C7B H7BB 108.2 . . ?
N8B C7B C6B 110.10(9) . . ?
N8B C7B H7BA 109.6 . . ?
N8B C7B H7BB 109.6 . . ?
C7B N8B H8B 117.8 . . ?
C2B' N8B C7B 124.39(10) . . ?
C2B' N8B H8B 117.8 . . ?
C2B' N1B' H1B' 119.7 . . ?
C6B' N1B' H1B' 119.7 . . ?
C6B' N1B' C2B' 120.67(10) . . ?
N8B C2B' N1B' 120.35(10) . . ?
N8B C2B' N3B' 118.82(10) . . ?
N3B' C2B' N1B' 120.83(10) . . ?
C4B' N3B' C2B' 117.76(10) . . ?
N3B' C4B' H4B' 118.1 . . ?
N3B' C4B' C5B' 123.77(11) . . ?
C5B' C4B' H4B' 118.1 . . ?
C4B' C5B' H5B' 121.7 . . ?
C6B' C5B' C4B' 116.68(11) . . ?
C6B' C5B' H5B' 121.7 . . ?
N1B' C6B' C5B' 120.22(11) . . ?
N1B' C6B' H6B' 119.9 . . ?
C5B' C6B' H6B' 119.9 . . ?
O3C N1C O2C 119.39(10) . . ?
O3C N1C O4C 121.30(10) . . ?
O4C N1C O2C 119.30(10) . . ?
O6C N5C O7C 119.22(10) . . ?
O8C N5C O6C 120.86(10) . . ?
O8C N5C O7C 119.92(10) . . ?
H1WA O1W H1WB 104.5 . . ?
H2WA O2W H2WB 104.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O1A H1A O1W 0.84 1.76 2.5975(12) 178.7 . yes
N8A H8A O2B 0.88 2.01 2.8731(13) 168.3 1_645 yes
N1A' H1A' O7C 0.88 1.96 2.8308(13) 171.9 . yes
C6A' H6A' O3C 0.95 2.35 3.1380(15) 139.8 1_656 yes
C6A' H6A' O8C 0.95 2.41 3.0905(15) 128.7 . yes
O1B H1B O2W 0.84 1.75 2.5933(12) 176.0 . yes
N8B H8B O2A 0.88 2.02 2.8853(13) 166.9 1_465 yes
N1B' H1B' O2C 0.88 1.97 2.8360(13) 168.9 . yes
C6B' H6B' O3C 0.95 2.38 3.0725(15) 129.5 . yes
C6B' H6B' O8C 0.95 2.32 3.0955(14) 138.0 1_454 yes
O1W H1WA O4C 0.87 2.10 2.8896(13) 150.2 . yes
O1W H1WB N3B' 0.87 2.03 2.9002(13) 173.1 1_645 yes
O2W H2WA N3A' 0.87 2.03 2.8961(14) 171.2 1_465 yes
O2W H2WB O6C 0.87 2.05 2.8529(13) 152.6 . yes

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
O1A C2A C3A C4A -178.12(10) . . . . ?
C2A C3A C4A C5A 172.71(10) . . . . ?
O2A C2A C3A C4A 0.97(18) . . . . ?
C3A C4A C5A C6A -178.78(10) . . . . ?
C4A C5A C6A C7A 179.82(10) . . . . ?
C5A C6A C7A N8A -179.26(9) . . . . ?
C6A C7A N8A C2A' 176.23(11) . . . . ?
C7A N8A C2A' N1A' 2.25(18) . . . . ?
C7A N8A C2A' N3A' -178.41(10) . . . . ?
N8A C2A' N3A' C4A' 179.26(11) . . . . ?
N1A' C2A' N3A' C4A' -1.40(17) . . . . ?
C2A' N1A' C6A' C5A' -0.78(17) . . . . ?
C2A' N3A' C4A' C5A' 0.43(19) . . . . ?
N3A' C4A' C5A' C6A' 0.35(19) . . . . ?
C4A' C5A' C6A' N1A' -0.17(18) . . . . ?
C6A' N1A' C2A' N8A -179.06(11) . . . . ?
C6A' N1A' C2A' N3A' 1.61(17) . . . . ?
O1B C2B C3B C4B -171.28(10) . . . . ?
C2B C3B C4B C5B 178.96(10) . . . . ?
O2B C2B C3B C4B 9.79(17) . . . . ?
C3B C4B C5B C6B 178.44(10) . . . . ?
C4B C5B C6B C7B -175.60(10) . . . . ?
C5B C6B C7B N8B 173.28(9) . . . . ?
C6B C7B N8B C2B' -177.10(10) . . . . ?
C7B N8B C2B' N1B' -0.33(17) . . . . ?
C7B N8B C2B' N3B' 179.82(10) . . . . ?
N8B C2B' N3B' C4B' -177.81(10) . . . . ?
N1B' C2B' N3B' C4B' 2.34(16) . . . . ?
C2B' N1B' C6B' C5B' 1.28(17) . . . . ?
C2B' N3B' C4B' C5B' -0.12(18) . . . . ?
N3B' C4B' C5B' C6B' -1.46(18) . . . . ?
C4B' C5B' C6B' N1B' 0.85(17) . . . . ?
C6B' N1B' C2B' N8B 177.18(10) . . . . ?
C6B' N1B' C2B' N3B' -2.97(16) . . . . ?

_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_32059501_0m
_database_code_depnum_ccdc_archive 'CCDC 2120750'
loop_
_audit_author_name
_audit_author_address
'Miquel Barcelo-Oliver'
;University of the Balearic Islands
Spain
;
_audit_update_record             
;
2022-11-14 deposited with the CCDC.	2022-11-24 downloaded from the CCDC.
;
_audit_creation_date             2022-11-14
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_chemical_formula_moiety         'C8 H10 N4 O3'
_chemical_formula_sum            'C8 H10 N4 O3'
_chemical_formula_weight         210.194
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.21560 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.00304 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.52900 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.25080 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2ybc (x-z,y,z)'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x+1/2,y+1/2,-z+1/2
3 -x,-y,-z
4 x-1/2,-y-1/2,z-1/2

_symmetry_Int_Tables_number      14
_cell_length_a                   4.6981(2)
_cell_length_b                   14.0421(6)
_cell_length_c                   14.3987(8)
_cell_angle_alpha                90
_cell_angle_beta                 99.168(2)
_cell_angle_gamma                90
_cell_volume                     937.76(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5264
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.31
_cell_measurement_theta_min      2.87
_exptl_absorpt_coefficient_mu    0.117
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.7041
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS-2016/2 (Bruker AXS Inc.)'
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.489
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             440.353
_exptl_crystal_size_max          0.257
_exptl_crystal_size_mid          0.111
_exptl_crystal_size_min          0.093
_diffrn_reflns_av_R_equivalents  0.0294
_diffrn_reflns_av_unetI/netI     0.0266
_diffrn_reflns_Laue_measured_fraction_full 0.9976
_diffrn_reflns_Laue_measured_fraction_max 0.9970
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            9730
_diffrn_reflns_point_group_measured_fraction_full 0.9976
_diffrn_reflns_point_group_measured_fraction_max 0.9970
_diffrn_reflns_theta_full        25.2417
_diffrn_reflns_theta_max         28.32
_diffrn_reflns_theta_min         2.87
_diffrn_ambient_temperature      100.15
_diffrn_measured_fraction_theta_full 0.9976
_diffrn_measured_fraction_theta_max 0.9970
_diffrn_measurement_device_type  'Bruker D8 Venture Photon 100 CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              5
_reflns_limit_h_min              -6
_reflns_limit_k_max              18
_reflns_limit_k_min              0
_reflns_limit_l_max              19
_reflns_limit_l_min              -4
_reflns_number_gt                2019
_reflns_number_total             2333
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.5 (Bourhis et al., 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_refine_diff_density_max         0.2661
_refine_diff_density_min         -0.2617
_refine_diff_density_rms         0.0611
_refine_ls_d_res_high            0.7490
_refine_ls_d_res_low             7.1074
_refine_ls_goodness_of_fit_ref   1.0525
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    12
_refine_ls_number_parameters     148
_refine_ls_number_reflns         2333
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0436
_refine_ls_R_factor_gt           0.0363
_refine_ls_restrained_S_all      1.0525
_refine_ls_shift/su_max          -0.0009
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0446P)²+0.3287P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0889
_refine_ls_wR_factor_ref         0.0930
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C3(H3a,H3b), C6(H6a,H6b)
2.b Aromatic/amide H refined with riding coordinates:
 C6'(H6'), C4'(H4'), C5'(H5')
;
_atom_sites_solution_primary     direct
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_refinement_flags_posn
O1 O -0.24044(18) 0.52438(6) 0.40770(6) 0.01776(19) Uani 1.000000 .
H1 H -0.161(4) 0.5112(14) 0.3479(15) 0.055(6) Uiso 1.000000 .
C2 C -0.1368(2) 0.60421(8) 0.44571(7) 0.0132(2) Uani 1.000000 .
O2 O 0.04462(17) 0.65316(6) 0.41636(5) 0.01730(19) Uani 1.000000 .
C3 C -0.2735(2) 0.63158(8) 0.52968(8) 0.0157(2) Uani 1.000000 .
H3a H -0.4773(2) 0.64927(8) 0.50819(8) 0.0189(3) Uiso 1.000000 R
H3b H -0.2709(2) 0.57593(8) 0.57201(8) 0.0189(3) Uiso 1.000000 R
N4 N -0.1260(2) 0.71062(7) 0.58169(6) 0.0141(2) Uani 1.000000 .
H4 H 0.056(4) 0.7178(10) 0.5842(10) 0.024(4) Uiso 1.000000 .
C5 C -0.2665(2) 0.76730(8) 0.63365(7) 0.0128(2) Uani 1.000000 .
O5 O -0.52549(17) 0.75876(6) 0.63674(6) 0.0219(2) Uani 1.000000 .
C6 C -0.0841(2) 0.84376(8) 0.69075(8) 0.0155(2) Uani 1.000000 .
H6a H 0.0680(2) 0.81263(8) 0.73613(8) 0.0186(3) Uiso 1.000000 R
H6b H 0.0117(2) 0.88320(8) 0.64781(8) 0.0186(3) Uiso 1.000000 R
N7 N -0.2545(2) 0.90440(7) 0.74121(7) 0.0148(2) Uani 1.000000 .
H7 H -0.304(3) 0.8833(10) 0.7953(10) 0.023(4) Uiso 1.000000 .
N1' N -0.5754(2) 1.02590(6) 0.75212(6) 0.0146(2) Uani 1.000000 .
C2' C -0.3914(2) 0.98226(7) 0.70193(7) 0.0140(2) Uani 1.000000 .
N3' N -0.3345(2) 1.01207(7) 0.61828(7) 0.0212(2) Uani 1.000000 .
C4' C -0.4679(3) 1.09151(9) 0.58454(8) 0.0256(3) Uani 1.000000 .
H4' H -0.4294(3) 1.11524(9) 0.52601(8) 0.0307(3) Uiso 1.000000 R
C5' C -0.6592(3) 1.14130(9) 0.62987(9) 0.0258(3) Uani 1.000000 .
H5' H -0.7520(3) 1.19760(9) 0.60400(9) 0.0309(3) Uiso 1.000000 R
C6' C -0.7075(3) 1.10459(8) 0.71480(8) 0.0196(2) Uani 1.000000 .
H6' H -0.8392(3) 1.13628(8) 0.74794(8) 0.0235(3) Uiso 1.000000 R


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 H1 1.01(2) . ?
O1 C2 1.3070(13) . ?
C2 O2 1.2217(13) . ?
C2 C3 1.5062(15) . ?
C3 H3a 0.9900 . ?
C3 H3b 0.9900 . ?
C3 N4 1.4517(14) . ?
N4 H4 0.857(16) . ?
N4 C5 1.3364(14) . ?
C5 O5 1.2307(13) . ?
C5 C6 1.5291(15) . ?
C6 H6a 0.9900 . ?
C6 H6b 0.9900 . ?
C6 N7 1.4419(13) . ?
N7 H7 0.898(15) . ?
N7 C2' 1.3464(14) . ?
N1' C2' 1.3578(14) . ?
N1' C6' 1.3375(14) . ?
C2' N3' 1.3419(15) . ?
N3' C4' 1.3329(16) . ?
C4' H4' 0.9500 . ?
C4' C5' 1.3816(18) . ?
C5' H5' 0.9500 . ?
C5' C6' 1.3789(17) . ?
C6' H6' 0.9500 . ?

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 110.6(11) . . ?
O2 C2 O1 124.85(10) . . ?
C3 C2 O1 112.15(9) . . ?
C3 C2 O2 122.97(10) . . ?
H3a C3 C2 109.14(6) . . ?
H3b C3 C2 109.14(6) . . ?
H3b C3 H3a 107.9 . . ?
N4 C3 C2 112.32(9) . . ?
N4 C3 H3a 109.14(6) . . ?
N4 C3 H3b 109.14(6) . . ?
H4 N4 C3 120.2(10) . . ?
C5 N4 C3 120.43(9) . . ?
C5 N4 H4 119.1(10) . . ?
O5 C5 N4 122.78(10) . . ?
C6 C5 N4 115.77(9) . . ?
C6 C5 O5 121.44(9) . . ?
H6a C6 C5 109.18(6) . . ?
H6b C6 C5 109.18(6) . . ?
H6b C6 H6a 107.9 . . ?
N7 C6 C5 112.15(9) . . ?
N7 C6 H6a 109.18(6) . . ?
N7 C6 H6b 109.18(6) . . ?
H7 N7 C6 119.0(9) . . ?
C2' N7 C6 122.30(9) . . ?
C2' N7 H7 117.3(9) . . ?
C6' N1' C2' 116.95(10) . . ?
N1' C2' N7 116.42(9) . . ?
N3' C2' N7 118.69(10) . . ?
N3' C2' N1' 124.88(10) . . ?
C4' N3' C2' 116.03(10) . . ?
H4' C4' N3' 118.15(7) . . ?
C5' C4' N3' 123.70(11) . . ?
C5' C4' H4' 118.15(7) . . ?
H5' C5' C4' 121.91(7) . . ?
C6' C5' C4' 116.19(11) . . ?
C6' C5' H5' 121.91(7) . . ?
C5' C6' N1' 122.25(11) . . ?
H6' C6' N1' 118.88(6) . . ?
H6' C6' C5' 118.88(7) . . ?

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 C2 C3 N4 170.03(9) . . . . ?
C2 C3 N4 C5 154.60(9) . . . . ?
C3 N4 C5 O5 -3.48(12) . . . . ?
C3 N4 C5 C6 175.85(10) . . . . ?
N4 C5 C6 N7 177.32(10) . . . . ?
C5 C6 N7 C2' -86.60(10) . . . . ?
C6 N7 C2' N1' 171.40(10) . . . . ?
C6 N7 C2' N3' -9.78(11) . . . . ?
N7 C2' N1' C6' 178.48(10) . . . . ?
N7 C2' N3' C4' -177.52(11) . . . . ?
N1' C2' N3' C4' 1.18(13) . . . . ?
N1' C6' C5' C4' 0.69(14) . . . . ?
C2' N3' C4' C5' -1.20(13) . . . . ?
N3' C4' C5' C6' 0.33(15) . . . . ?


_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1_a_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 2120747'
loop_
_audit_author_name
_audit_author_address
'Miquel Barcelo-Oliver'
;University of the Balearic Islands
Spain
;
_audit_update_record             
;
2022-11-14 deposited with the CCDC.	2022-11-24 downloaded from the CCDC.
;
_audit_creation_date             2022-11-14
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_chemical_formula_moiety         'C9 H14 N3 O2, N O3'
_chemical_formula_sum            'C9 H14 N4 O5'
_chemical_formula_weight         258.235
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
C 0.01920 0.00962 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.21560 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.00304 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.03256 0.01839 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.52900 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.05239 0.03376 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.25080 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_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_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,y+1/2,-z+1/2
3 -x,-y,-z
4 x,-y-1/2,z-1/2

_symmetry_Int_Tables_number      14
_cell_length_a                   9.3661(3)
_cell_length_b                   36.0462(12)
_cell_length_c                   7.5101(3)
_cell_angle_alpha                90
_cell_angle_beta                 109.840(1)
_cell_angle_gamma                90
_cell_volume                     2385.01(15)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9916
_cell_measurement_temperature    298.0
_cell_measurement_theta_max      66.661
_cell_measurement_theta_min      4.909
_exptl_absorpt_coefficient_mu    1.016
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_correction_T_min  0.5696
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1321 before and 0.0732 after correction.
The Ratio of minimum to maximum transmission is 0.7566.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.438
_exptl_crystal_description       block
_exptl_crystal_F_000             1092.523
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.14
_diffrn_reflns_av_R_equivalents  0.0418
_diffrn_reflns_av_unetI/netI     0.0385
_diffrn_reflns_Laue_measured_fraction_full 0.9929
_diffrn_reflns_Laue_measured_fraction_max 0.9929
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       42
_diffrn_reflns_limit_k_min       -42
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            21222
_diffrn_reflns_point_group_measured_fraction_full 0.9929
_diffrn_reflns_point_group_measured_fraction_max 0.9929
_diffrn_reflns_theta_full        66.7859
_diffrn_reflns_theta_max         66.79
_diffrn_reflns_theta_min         2.45
_diffrn_ambient_temperature      298.00
_diffrn_measured_fraction_theta_full 0.9929
_diffrn_measured_fraction_theta_max 0.9929
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              10
_reflns_limit_h_min              -11
_reflns_limit_k_max              42
_reflns_limit_k_min              0
_reflns_limit_l_max              8
_reflns_limit_l_min              0
_reflns_number_gt                3929
_reflns_number_total             4206
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'Bruker Apex3, 2016'
_computing_data_collection       'Bruker Apex3, 2016'
_computing_data_reduction        'SAINT v8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.5 (Bourhis et al., 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.3378
_refine_diff_density_min         -0.2609
_refine_diff_density_rms         0.0397
_refine_ls_d_res_high            0.8388
_refine_ls_d_res_low             18.0231
_refine_ls_goodness_of_fit_ref   1.0445
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    48
_refine_ls_number_parameters     327
_refine_ls_number_reflns         4206
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0621
_refine_ls_R_factor_gt           0.0597
_refine_ls_restrained_S_all      1.0445
_refine_ls_shift/su_max          -0.0005
_refine_ls_shift/su_mean         0.0001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0521P)²+1.1353P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1507
_refine_ls_wR_factor_ref         0.1523
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C6B(H6Ba,H6Bb), C5B(H5Ba,H5Bb), C4B(H4Ba,H4Bb), C3B(H3Ba,H3Bb), C6A(H6Aa,
 H6Ab), C5A(H5Aa,H5Ab), C4A(H4Aa,H4Ab), C3A(H3Aa,H3Ab)
2.b Aromatic/amide H refined with riding coordinates:
 N1B'(H1B'), C4B'(H4B'), C5B'(H5B'), C6B'(H6B'), N7B(H7B), N1A'(H1A'),
 C4A'(H4A'), C5A'(H5A'), C6A'(H6A'), N7A(H7A)
2.c Idealised tetrahedral OH refined as rotating group:
 O1B(H1B), O1A(H1A)
;
_atom_sites_solution_primary     dual
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_refinement_flags_posn
O1B O 0.5740(2) 0.50007(5) 0.7635(3) 0.1064(8) Uani 1.000000 .
H1B H 0.5197(6) 0.48209(17) 0.720(5) 0.1596(11) Uiso 1.000000 GR
C2B C 0.4907(3) 0.53000(6) 0.7358(3) 0.0658(6) Uani 1.000000 .
O2B O 0.36017(18) 0.53028(5) 0.6350(2) 0.0786(5) Uani 1.000000 .
C3B C 0.5770(3) 0.56287(6) 0.8379(3) 0.0694(6) Uani 1.000000 .
H3Ba H 0.5932(3) 0.56017(6) 0.9718(3) 0.0833(7) Uiso 1.000000 R
H3Bb H 0.6759(3) 0.56309(6) 0.8229(3) 0.0833(7) Uiso 1.000000 R
C4B C 0.5006(3) 0.59970(6) 0.7717(3) 0.0660(6) Uani 1.000000 .
H4Ba H 0.4695(3) 0.60099(6) 0.6348(3) 0.0792(7) Uiso 1.000000 R
H4Bb H 0.4102(3) 0.60149(6) 0.8066(3) 0.0792(7) Uiso 1.000000 R
C5B C 0.6050(3) 0.63215(6) 0.8572(3) 0.0675(6) Uani 1.000000 .
H5Ba H 0.6276(3) 0.63238(6) 0.9932(3) 0.0811(7) Uiso 1.000000 R
H5Bb H 0.6998(3) 0.62906(6) 0.8333(3) 0.0811(7) Uiso 1.000000 R
C6B C 0.5341(3) 0.66836(6) 0.7757(4) 0.0709(6) Uani 1.000000 .
H6Ba H 0.5107(3) 0.66810(6) 0.6396(4) 0.0851(8) Uiso 1.000000 R
H6Bb H 0.4398(3) 0.67161(6) 0.8006(4) 0.0851(8) Uiso 1.000000 R
N7B N 0.6359(2) 0.69933(5) 0.8576(3) 0.0685(5) Uani 1.000000 .
H7B H 0.7255(2) 0.69465(5) 0.9351(3) 0.0823(6) Uiso 1.000000 R
N1B' N 0.6906(2) 0.76197(5) 0.9070(3) 0.0632(5) Uani 1.000000 .
H1B' H 0.7779(2) 0.75656(5) 0.9882(3) 0.0758(6) Uiso 1.000000 R
C2B' C 0.5954(2) 0.73420(6) 0.8170(3) 0.0580(5) Uani 1.000000 .
N3B' N 0.4600(2) 0.74160(5) 0.6871(3) 0.0660(5) Uani 1.000000 .
C4B' C 0.4228(3) 0.77685(7) 0.6539(3) 0.0692(6) Uani 1.000000 .
H4B' H 0.3290(3) 0.78236(7) 0.5639(3) 0.0830(7) Uiso 1.000000 R
C5B' C 0.5138(3) 0.80611(7) 0.7440(4) 0.0695(6) Uani 1.000000 .
H5B' H 0.4819(3) 0.83056(7) 0.7178(4) 0.0834(7) Uiso 1.000000 R
C6B' C 0.6507(3) 0.79784(6) 0.8712(3) 0.0674(6) Uani 1.000000 .
H6B' H 0.7168(3) 0.81664(6) 0.9335(3) 0.0809(7) Uiso 1.000000 R
N1C N 1.0123(2) 0.67430(6) 0.7516(3) 0.0745(6) Uani 1.000000 .
O2C O 1.1404(2) 0.66993(6) 0.8598(3) 0.1093(7) Uani 1.000000 .
O3C O 0.9217(3) 0.64930(6) 0.7048(4) 0.1202(8) Uani 1.000000 .
O4C O 0.9697(3) 0.70546(5) 0.6814(4) 0.1237(9) Uani 1.000000 .
O1A O 1.1364(2) 0.73679(5) 1.3112(3) 0.1051(7) Uani 1.000000 .
H1A H 1.0885(10) 0.75615(5) 1.280(6) 0.1576(11) Uiso 1.000000 GR
C2A C 1.0451(3) 0.70868(7) 1.2534(3) 0.0688(6) Uani 1.000000 .
O2A O 0.91491(19) 0.71224(5) 1.1520(3) 0.0879(6) Uani 1.000000 .
C3A C 1.1193(3) 0.67234(7) 1.3232(4) 0.0735(7) Uani 1.000000 .
H3Aa H 1.2060(3) 0.66953(7) 1.2813(4) 0.0882(8) Uiso 1.000000 R
H3Ab H 1.1572(3) 0.67271(7) 1.4604(4) 0.0882(8) Uiso 1.000000 R
C4A C 1.0175(2) 0.63918(7) 1.2580(4) 0.0681(6) Uani 1.000000 .
H4Aa H 0.9318(2) 0.64146(7) 1.3020(4) 0.0818(7) Uiso 1.000000 R
H4Ab H 0.9785(2) 0.63870(7) 1.1207(4) 0.0818(7) Uiso 1.000000 R
C5A C 1.0998(3) 0.60303(7) 1.3306(3) 0.0687(6) Uani 1.000000 .
H5Aa H 1.1879(3) 0.60123(7) 1.2909(3) 0.0825(7) Uiso 1.000000 R
H5Ab H 1.1352(3) 0.60310(7) 1.4679(3) 0.0825(7) Uiso 1.000000 R
C6A C 0.9996(2) 0.56968(6) 1.2590(3) 0.0642(6) Uani 1.000000 .
H6Aa H 0.9118(2) 0.57116(6) 1.2993(3) 0.0771(7) Uiso 1.000000 R
H6Ab H 0.9641(2) 0.56936(6) 1.1217(3) 0.0771(7) Uiso 1.000000 R
N7A N 1.0840(2) 0.53556(5) 1.3322(3) 0.0678(5) Uani 1.000000 .
H7A H 1.1737(2) 0.53747(5) 1.4144(3) 0.0814(6) Uiso 1.000000 R
N1A' N 1.1131(2) 0.47199(5) 1.3575(3) 0.0659(5) Uani 1.000000 .
H1A' H 1.2016(2) 0.47498(5) 1.4412(3) 0.0791(6) Uiso 1.000000 R
C2A' C 1.0300(2) 0.50226(6) 1.2789(3) 0.0605(5) Uani 1.000000 .
N3A' N 0.8910(2) 0.49843(5) 1.1469(3) 0.0660(5) Uani 1.000000 .
C4A' C 0.8416(3) 0.46436(7) 1.1018(3) 0.0702(6) Uani 1.000000 .
H4A' H 0.7458(3) 0.46139(7) 1.0114(3) 0.0843(7) Uiso 1.000000 R
C5A' C 0.9221(3) 0.43255(7) 1.1791(4) 0.0718(6) Uani 1.000000 .
H5A' H 0.8822(3) 0.40899(7) 1.1433(4) 0.0861(8) Uiso 1.000000 R
C6A' C 1.0613(3) 0.43756(7) 1.3088(3) 0.0708(6) Uani 1.000000 .
H6A' H 1.1209(3) 0.41720(7) 1.3639(3) 0.0849(8) Uiso 1.000000 R
N5C N 0.5710(2) 0.58617(5) 0.3271(3) 0.0666(5) Uani 1.000000 .
O6C O 0.6085(2) 0.55405(5) 0.3913(3) 0.0960(6) Uani 1.000000 .
O7C O 0.6640(2) 0.61085(5) 0.3852(3) 0.1096(7) Uani 1.000000 .
O8C O 0.4441(2) 0.59135(6) 0.2129(3) 0.0933(6) Uani 1.000000 .


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
O1B H1B 0.8200 . ?
O1B C2B 1.306(3) . ?
C2B O2B 1.200(3) . ?
C2B C3B 1.492(3) . ?
C3B H3Ba 0.9700 . ?
C3B H3Bb 0.9700 . ?
C3B C4B 1.510(3) . ?
C4B H4Ba 0.9700 . ?
C4B H4Bb 0.9700 . ?
C4B C5B 1.520(3) . ?
C5B H5Ba 0.9700 . ?
C5B H5Bb 0.9700 . ?
C5B C6B 1.497(3) . ?
C6B H6Ba 0.9700 . ?
C6B H6Bb 0.9700 . ?
C6B N7B 1.462(3) . ?
N7B H7B 0.8600 . ?
N7B C2B' 1.319(3) . ?
N1B' H1B' 0.8600 . ?
N1B' C2B' 1.358(3) . ?
N1B' C6B' 1.347(3) . ?
C2B' N3B' 1.338(3) . ?
N3B' C4B' 1.319(3) . ?
C4B' H4B' 0.9300 . ?
C4B' C5B' 1.380(3) . ?
C5B' H5B' 0.9300 . ?
C5B' C6B' 1.347(3) . ?
C6B' H6B' 0.9300 . ?
N1C O2C 1.209(3) . ?
N1C O3C 1.205(3) . ?
N1C O4C 1.247(3) . ?
O1A H1A 0.8200 . ?
O1A C2A 1.301(3) . ?
C2A O2A 1.205(3) . ?
C2A C3A 1.492(3) . ?
C3A H3Aa 0.9700 . ?
C3A H3Ab 0.9700 . ?
C3A C4A 1.504(3) . ?
C4A H4Aa 0.9700 . ?
C4A H4Ab 0.9700 . ?
C4A C5A 1.518(3) . ?
C5A H5Aa 0.9700 . ?
C5A H5Ab 0.9700 . ?
C5A C6A 1.508(3) . ?
C6A H6Aa 0.9700 . ?
C6A H6Ab 0.9700 . ?
C6A N7A 1.465(3) . ?
N7A H7A 0.8600 . ?
N7A C2A' 1.312(3) . ?
N1A' H1A' 0.8600 . ?
N1A' C2A' 1.354(3) . ?
N1A' C6A' 1.337(3) . ?
C2A' N3A' 1.349(3) . ?
N3A' C4A' 1.315(3) . ?
C4A' H4A' 0.9300 . ?
C4A' C5A' 1.387(3) . ?
C5A' H5A' 0.9300 . ?
C5A' C6A' 1.348(3) . ?
C6A' H6A' 0.9300 . ?
N5C O6C 1.257(2) . ?
N5C O7C 1.217(3) . ?
N5C O8C 1.221(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
C2B O1B H1B 109.5 . . ?
O2B C2B O1B 122.2(2) . . ?
C3B C2B O1B 112.57(19) . . ?
C3B C2B O2B 125.2(2) . . ?
H3Ba C3B C2B 108.63(14) . . ?
H3Bb C3B C2B 108.63(14) . . ?
H3Bb C3B H3Ba 107.6 . . ?
C4B C3B C2B 114.54(19) . . ?
C4B C3B H3Ba 108.63(13) . . ?
C4B C3B H3Bb 108.63(13) . . ?
H4Ba C4B C3B 109.24(13) . . ?
H4Bb C4B C3B 109.24(14) . . ?
H4Bb C4B H4Ba 107.9 . . ?
C5B C4B C3B 111.87(19) . . ?
C5B C4B H4Ba 109.24(13) . . ?
C5B C4B H4Bb 109.24(13) . . ?
H5Ba C5B C4B 109.33(13) . . ?
H5Bb C5B C4B 109.33(13) . . ?
H5Bb C5B H5Ba 108.0 . . ?
C6B C5B C4B 111.46(19) . . ?
C6B C5B H5Ba 109.33(14) . . ?
C6B C5B H5Bb 109.33(14) . . ?
H6Ba C6B C5B 109.44(14) . . ?
H6Bb C6B C5B 109.44(14) . . ?
H6Bb C6B H6Ba 108.0 . . ?
N7B C6B C5B 111.00(19) . . ?
N7B C6B H6Ba 109.44(13) . . ?
N7B C6B H6Bb 109.44(13) . . ?
H7B N7B C6B 118.82(12) . . ?
C2B' N7B C6B 122.35(19) . . ?
C2B' N7B H7B 118.82(12) . . ?
C2B' N1B' H1B' 119.44(12) . . ?
C6B' N1B' H1B' 119.44(13) . . ?
C6B' N1B' C2B' 121.13(19) . . ?
N1B' C2B' N7B 119.89(19) . . ?
N3B' C2B' N7B 119.1(2) . . ?
N3B' C2B' N1B' 121.0(2) . . ?
C4B' N3B' C2B' 117.03(19) . . ?
H4B' C4B' N3B' 117.85(13) . . ?
C5B' C4B' N3B' 124.3(2) . . ?
C5B' C4B' H4B' 117.85(14) . . ?
H5B' C5B' C4B' 121.32(14) . . ?
C6B' C5B' C4B' 117.4(2) . . ?
C6B' C5B' H5B' 121.32(15) . . ?
C5B' C6B' N1B' 119.1(2) . . ?
H6B' C6B' N1B' 120.43(13) . . ?
H6B' C6B' C5B' 120.43(15) . . ?
O3C N1C O2C 122.5(2) . . ?
O4C N1C O2C 120.2(2) . . ?
O4C N1C O3C 117.2(2) . . ?
C2A O1A H1A 109.5 . . ?
O2A C2A O1A 122.5(2) . . ?
C3A C2A O1A 113.0(2) . . ?
C3A C2A O2A 124.5(2) . . ?
H3Aa C3A C2A 108.63(14) . . ?
H3Ab C3A C2A 108.63(14) . . ?
H3Ab C3A H3Aa 107.6 . . ?
C4A C3A C2A 114.52(19) . . ?
C4A C3A H3Aa 108.63(14) . . ?
C4A C3A H3Ab 108.63(14) . . ?
H4Aa C4A C3A 109.18(14) . . ?
H4Ab C4A C3A 109.18(14) . . ?
H4Ab C4A H4Aa 107.9 . . ?
C5A C4A C3A 112.14(19) . . ?
C5A C4A H4Aa 109.18(13) . . ?
C5A C4A H4Ab 109.18(14) . . ?
H5Aa C5A C4A 109.17(13) . . ?
H5Ab C5A C4A 109.17(14) . . ?
H5Ab C5A H5Aa 107.9 . . ?
C6A C5A C4A 112.19(19) . . ?
C6A C5A H5Aa 109.17(13) . . ?
C6A C5A H5Ab 109.17(13) . . ?
H6Aa C6A C5A 109.63(13) . . ?
H6Ab C6A C5A 109.63(13) . . ?
H6Ab C6A H6Aa 108.1 . . ?
N7A C6A C5A 110.13(18) . . ?
N7A C6A H6Aa 109.63(12) . . ?
N7A C6A H6Ab 109.63(12) . . ?
H7A N7A C6A 118.30(12) . . ?
C2A' N7A C6A 123.39(18) . . ?
C2A' N7A H7A 118.30(12) . . ?
C2A' N1A' H1A' 119.11(13) . . ?
C6A' N1A' H1A' 119.11(13) . . ?
C6A' N1A' C2A' 121.8(2) . . ?
N1A' C2A' N7A 119.9(2) . . ?
N3A' C2A' N7A 119.6(2) . . ?
N3A' C2A' N1A' 120.4(2) . . ?
C4A' N3A' C2A' 116.9(2) . . ?
H4A' C4A' N3A' 117.60(13) . . ?
C5A' C4A' N3A' 124.8(2) . . ?
C5A' C4A' H4A' 117.60(15) . . ?
H5A' C5A' C4A' 121.75(15) . . ?
C6A' C5A' C4A' 116.5(2) . . ?
C6A' C5A' H5A' 121.75(15) . . ?
C5A' C6A' N1A' 119.6(2) . . ?
H6A' C6A' N1A' 120.20(13) . . ?
H6A' C6A' C5A' 120.20(15) . . ?
O7C N5C O6C 117.6(2) . . ?
O8C N5C O6C 119.2(2) . . ?
O8C N5C O7C 123.2(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1B C2B C3B C4B 164.7(2) . . . . ?
C2B C3B C4B C5B -170.5(2) . . . . ?
C3B C4B C5B C6B 174.2(2) . . . . ?
C4B C5B C6B N7B -179.5(2) . . . . ?
C5B C6B N7B C2B' -175.7(2) . . . . ?
C6B N7B C2B' N1B' 175.5(2) . . . . ?
C6B N7B C2B' N3B' -4.4(3) . . . . ?
N7B C2B' N1B' C6B' -178.6(2) . . . . ?
N7B C2B' N3B' C4B' 178.6(2) . . . . ?
N1B' C2B' N3B' C4B' -1.3(3) . . . . ?
N1B' C6B' C5B' C4B' -1.3(3) . . . . ?
C2B' N3B' C4B' C5B' -0.0(3) . . . . ?
N3B' C4B' C5B' C6B' 1.4(3) . . . . ?
O1A C2A C3A C4A -179.6(2) . . . . ?
C2A C3A C4A C5A 179.1(2) . . . . ?
C3A C4A C5A C6A -177.7(2) . . . . ?
C4A C5A C6A N7A 179.8(2) . . . . ?
C5A C6A N7A C2A' -173.29(19) . . . . ?
C6A N7A C2A' N1A' -177.9(2) . . . . ?
C6A N7A C2A' N3A' 1.5(2) . . . . ?
N7A C2A' N1A' C6A' 179.2(2) . . . . ?
N7A C2A' N3A' C4A' -178.7(2) . . . . ?
N1A' C2A' N3A' C4A' 0.7(3) . . . . ?
N1A' C6A' C5A' C4A' 0.9(3) . . . . ?
C2A' N3A' C4A' C5A' -0.3(3) . . . . ?
N3A' C4A' C5A' C6A' -0.5(3) . . . . ?


_olex2_submission_special_instructions 'No special instructions were received'
