# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2023

####################################################################### 
# 
# 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_L210623_a
_database_code_depnum_ccdc_archive 'CCDC 2246513'
loop_
_audit_author_name
_audit_author_address
'Ying He'
;Nanjing University of Science and Technology
China
;
_audit_update_record             
;
2023-03-06 deposited with the CCDC.	2023-04-30 downloaded from the CCDC.
;
_audit_creation_date             2022-11-21
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C6 H7 N8, Cl, H2 O'
_chemical_formula_sum            'C6 H9 Cl N8 O'
_chemical_formula_weight         244.66
_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'
Cl Cl 0.1484 0.1585 '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                   6.9239(5)
_cell_length_b                   8.6109(6)
_cell_length_c                   17.0430(12)
_cell_angle_alpha                90
_cell_angle_beta                 93.587(2)
_cell_angle_gamma                90
_cell_volume                     1014.13(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5699
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.50
_cell_measurement_theta_min      2.65
_shelx_estimated_absorpt_T_max   0.929
_shelx_estimated_absorpt_T_min   0.910
_exptl_absorpt_coefficient_mu    0.372
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6788
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.602
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             504
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0246
_diffrn_reflns_av_unetI/netI     0.0230
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            9212
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.520
_diffrn_reflns_theta_min         2.651
_diffrn_ambient_temperature      296(2)
_diffrn_detector_area_resol_mean 10.42
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON 100'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source.source            'Ius 2.0'
_diffrn_source.type              microfocus
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1987
_reflns_number_total             2316
_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  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.362
_refine_diff_density_min         -0.428
_refine_diff_density_rms         0.050
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     157
_refine_ls_number_reflns         2316
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0451
_refine_ls_R_factor_gt           0.0369
_refine_ls_restrained_S_all      1.042
_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)+(0.0556P)²+0.4070P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0987
_refine_ls_wR_factor_ref         0.1044
_refine_special_details          ?
_olex2_refinement_description    
;
1. Restrained distances
 O1-H1C = O1-H1D
 0.85 with sigma of 0.02
 H1C-H1D
 1.39 with sigma of 0.02
2.a Aromatic/amide H refined with riding coordinates:
 C4(H4)
2.b X=CH2 refined with riding coordinates:
 N1(H1A,H1B), N4(H4A,H4B)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.3635(2) 0.22189(17) 0.46181(9) 0.0241(3) Uani 1 1 d . . . . .
C2 C 0.3022(2) 0.38070(17) 0.45793(8) 0.0222(3) Uani 1 1 d . . . . .
C3 C 0.26453(19) 0.41966(17) 0.53577(8) 0.0224(3) Uani 1 1 d . . . . .
C4 C 0.2068(2) 0.56975(17) 0.55806(8) 0.0242(3) Uani 1 1 d . . . . .
H4 H 0.180827 0.594280 0.609488 0.029 Uiso 1 1 calc R U . . .
C5 C 0.1921(2) 0.67536(17) 0.49917(8) 0.0233(3) Uani 1 1 d . . . . .
C6 C 0.2882(2) 0.49596(17) 0.39989(8) 0.0239(3) Uani 1 1 d . . . . .
Cl1 Cl 0.25074(8) 0.83228(5) 0.26748(3) 0.04675(17) Uani 1 1 d . . . . .
N1 N 0.4279(2) 0.13271(16) 0.40257(8) 0.0326(3) Uani 1 1 d . . . . .
H1A H 0.469066 0.040023 0.412244 0.039 Uiso 1 1 calc R U . . .
H1B H 0.427208 0.169213 0.355590 0.039 Uiso 1 1 calc R U . . .
N2 N 0.36236(19) 0.16957(14) 0.53491(8) 0.0280(3) Uani 1 1 d . . . . .
N3 N 0.30218(19) 0.29318(15) 0.57899(8) 0.0268(3) Uani 1 1 d . . . . .
H3 H 0.279(3) 0.285(2) 0.6266(11) 0.032 Uiso 1 1 d . U . . .
N4 N 0.3290(2) 0.47882(17) 0.32558(8) 0.0376(4) Uani 1 1 d . . . . .
H4A H 0.318604 0.556493 0.293876 0.045 Uiso 1 1 calc R U . . .
H4B H 0.365989 0.389994 0.308974 0.045 Uiso 1 1 calc R U . . .
N5 N 0.23042(18) 0.63864(15) 0.42320(7) 0.0243(3) Uani 1 1 d . . . . .
H5 H 0.231(3) 0.710(2) 0.3917(10) 0.029 Uiso 1 1 d . U . . .
N6 N 0.1398(2) 0.83246(15) 0.50370(8) 0.0309(3) Uani 1 1 d . . . . .
N7 N 0.1183(2) 0.88046(16) 0.57173(8) 0.0316(3) Uani 1 1 d . . . . .
N8 N 0.0951(3) 0.93932(19) 0.62882(9) 0.0501(4) Uani 1 1 d . . . . .
O1 O 0.1877(2) 0.31052(16) 0.73647(8) 0.0444(3) Uani 1 1 d D . . . .
H1C H 0.182(3) 0.4078(18) 0.7425(15) 0.067 Uiso 1 1 d D U . . .
H1D H 0.075(3) 0.272(3) 0.7352(15) 0.067 Uiso 1 1 d D 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
C1 C2 1.432(2) . ?
C1 N1 1.365(2) . ?
C1 N2 1.3253(19) . ?
C2 C3 1.408(2) . ?
C2 C6 1.400(2) . ?
C3 C4 1.412(2) . ?
C3 N3 1.3314(19) . ?
C4 H4 0.9300 . ?
C4 C5 1.354(2) . ?
C5 N5 1.3747(19) . ?
C5 N6 1.4039(19) . ?
C6 N4 1.3231(19) . ?
C6 N5 1.359(2) . ?
N1 H1A 0.8600 . ?
N1 H1B 0.8600 . ?
N2 N3 1.3820(18) . ?
N3 H3 0.839(19) . ?
N4 H4A 0.8600 . ?
N4 H4B 0.8600 . ?
N5 H5 0.81(2) . ?
N6 N7 1.2486(19) . ?
N7 N8 1.117(2) . ?
O1 H1C 0.845(16) . ?
O1 H1D 0.844(15) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 C2 127.76(14) . . ?
N2 C1 C2 110.42(13) . . ?
N2 C1 N1 121.69(14) . . ?
C3 C2 C1 104.81(13) . . ?
C6 C2 C1 135.78(14) . . ?
C6 C2 C3 119.20(13) . . ?
C2 C3 C4 122.94(13) . . ?
N3 C3 C2 106.55(12) . . ?
N3 C3 C4 130.45(13) . . ?
C3 C4 H4 122.4 . . ?
C5 C4 C3 115.14(13) . . ?
C5 C4 H4 122.4 . . ?
C4 C5 N5 122.27(13) . . ?
C4 C5 N6 127.90(13) . . ?
N5 C5 N6 109.83(13) . . ?
N4 C6 C2 125.99(14) . . ?
N4 C6 N5 117.72(14) . . ?
N5 C6 C2 116.29(13) . . ?
C1 N1 H1A 120.0 . . ?
C1 N1 H1B 120.0 . . ?
H1A N1 H1B 120.0 . . ?
C1 N2 N3 105.60(12) . . ?
C3 N3 N2 112.62(12) . . ?
C3 N3 H3 124.4(13) . . ?
N2 N3 H3 122.6(13) . . ?
C6 N4 H4A 120.0 . . ?
C6 N4 H4B 120.0 . . ?
H4A N4 H4B 120.0 . . ?
C5 N5 H5 117.2(13) . . ?
C6 N5 C5 124.12(13) . . ?
C6 N5 H5 118.2(13) . . ?
N7 N6 C5 114.60(13) . . ?
N8 N7 N6 172.14(16) . . ?
H1C O1 H1D 110(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
C4 H4 Cl1 0.93 2.78 3.6615(15) 158.8 4_576 yes
N1 H1A N2 0.86 2.30 3.1346(19) 163.0 3_656 yes
N1 H1B O1 0.86 2.55 3.229(2) 137.1 4_565 yes
N3 H3 O1 0.839(19) 2.027(19) 2.8497(18) 166.5(19) . yes
N4 H4A Cl1 0.86 2.46 3.2359(15) 151.0 . yes
N4 H4B O1 0.86 2.42 3.047(2) 130.6 4_565 yes
N5 H5 Cl1 0.81(2) 2.377(19) 3.1449(14) 157.5(17) . yes
O1 H1C Cl1 0.845(16) 2.322(15) 3.1466(15) 165(2) 4_576 yes
O1 H1D Cl1 0.844(15) 2.428(16) 3.2721(16) 179(2) 3_566 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
C1 C2 C3 C4 177.57(13) . . . . ?
C1 C2 C3 N3 0.09(15) . . . . ?
C1 C2 C6 N4 2.4(3) . . . . ?
C1 C2 C6 N5 -176.37(15) . . . . ?
C1 N2 N3 C3 0.51(17) . . . . ?
C2 C1 N2 N3 -0.43(16) . . . . ?
C2 C3 C4 C5 -0.7(2) . . . . ?
C2 C3 N3 N2 -0.37(16) . . . . ?
C2 C6 N5 C5 2.1(2) . . . . ?
C3 C2 C6 N4 176.20(15) . . . . ?
C3 C2 C6 N5 -2.6(2) . . . . ?
C3 C4 C5 N5 0.1(2) . . . . ?
C3 C4 C5 N6 -179.48(14) . . . . ?
C4 C3 N3 N2 -177.59(14) . . . . ?
C4 C5 N5 C6 -0.8(2) . . . . ?
C4 C5 N6 N7 5.5(2) . . . . ?
C6 C2 C3 C4 2.1(2) . . . . ?
C6 C2 C3 N3 -175.42(12) . . . . ?
N1 C1 C2 C3 -175.74(15) . . . . ?
N1 C1 C2 C6 -1.4(3) . . . . ?
N1 C1 N2 N3 175.82(14) . . . . ?
N2 C1 C2 C3 0.22(16) . . . . ?
N2 C1 C2 C6 174.60(16) . . . . ?
N3 C3 C4 C5 176.09(14) . . . . ?
N4 C6 N5 C5 -176.82(14) . . . . ?
N5 C5 N6 N7 -174.12(13) . . . . ?
N6 C5 N5 C6 178.81(13) . . . . ?

_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_CWH211119_a
_database_code_depnum_ccdc_archive 'CCDC 2246541'
loop_
_audit_author_name
_audit_author_address
'Ying He'
;Nanjing University of Science and Technology
China
;
_audit_update_record             
;
2023-03-06 deposited with the CCDC.	2023-04-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 H7 N8, N O3, H2 O'
_chemical_formula_sum            'C6 H9 N9 O4'
_chemical_formula_weight         271.22

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

_space_group_crystal_system      monoclinic
_space_group_IT_number           11
_space_group_name_H-M_alt        'P 21/m'
_space_group_name_Hall           '-P 2yb'

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

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

_cell_length_a                   9.2168(14)
_cell_length_b                   6.5123(11)
_cell_length_c                   10.2460(15)
_cell_angle_alpha                90
_cell_angle_beta                 115.755(4)
_cell_angle_gamma                90
_cell_volume                     553.90(15)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2393
_cell_measurement_theta_min      2.21
_cell_measurement_theta_max      26.21

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.626
_exptl_crystal_F_000             280
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.010
_exptl_crystal_size_min          0.010
_exptl_absorpt_coefficient_mu    0.138
_shelx_estimated_absorpt_T_min   0.980
_shelx_estimated_absorpt_T_max   0.999
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5983
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_source.type              microfocus
_diffrn_radiation_type           MoK\a
_diffrn_source.source            'Ius 2.0'
_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON 100'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 10.42
_diffrn_reflns_number            6862
_diffrn_reflns_av_unetI/netI     0.0552
_diffrn_reflns_av_R_equivalents  0.0558
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.207
_diffrn_reflns_theta_max         27.487
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             1383
_reflns_number_gt                873
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0479P)²+0.3242P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1383
_refine_ls_number_parameters     118
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1010
_refine_ls_R_factor_gt           0.0540
_refine_ls_wR_factor_ref         0.1263
_refine_ls_wR_factor_gt          0.1114
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_restrained_S_all      1.034
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.2187(4) 0.250000 0.3439(3) 0.0318(7) Uani 1 2 d S T P . .
C2 C 0.4840(4) 0.250000 0.4856(3) 0.0267(7) Uani 1 2 d S T P . .
C3 C 0.6512(4) 0.250000 0.5295(3) 0.0287(7) Uani 1 2 d S T P . .
H3A H 0.725082 0.250000 0.626633 0.034 Uiso 1 2 calc R U P . .
C4 C 0.6974(4) 0.250000 0.4215(3) 0.0304(7) Uani 1 2 d S T P . .
C5 C 0.4262(4) 0.250000 0.2310(3) 0.0293(7) Uani 1 2 d S T P . .
C6 C 0.3710(3) 0.250000 0.3394(3) 0.0273(7) Uani 1 2 d S T P . .
N1 N 0.2357(3) 0.250000 0.4780(3) 0.0337(7) Uani 1 2 d S T P . .
N2 N 0.3986(3) 0.250000 0.5630(2) 0.0310(6) Uani 1 2 d S T P . .
H2 H 0.441382 0.250000 0.656160 0.037 Uiso 1 2 calc R U P . .
N3 N 0.5881(3) 0.250000 0.2782(3) 0.0328(7) Uani 1 2 d S T P . .
H3 H 0.624902 0.250000 0.214174 0.039 Uiso 1 2 calc R U P . .
N4 N 0.0668(3) 0.250000 0.2285(3) 0.0426(8) Uani 1 2 d S T P . .
H4A H -0.005046 0.250000 0.255557 0.051 Uiso 1 2 d R U P . .
H4B H 0.059154 0.139900 0.173057 0.051 Uiso 0.5 1 d R U P . .
N5 N 0.3348(3) 0.250000 0.0896(2) 0.0394(7) Uani 1 2 d S T P . .
H5A H 0.378640 0.250000 0.030651 0.047 Uiso 1 2 calc R U P . .
H5B H 0.231639 0.250000 0.056563 0.047 Uiso 1 2 calc R U P . .
N6 N 0.8549(3) 0.250000 0.4348(3) 0.0418(8) Uani 1 2 d S T P . .
N7 N 0.9607(4) 0.250000 0.5631(3) 0.0506(9) Uani 1 2 d S T P . .
N8 N 1.0656(4) 0.250000 0.6703(4) 0.0875(15) Uani 1 2 d S T P . .
N9 N 0.6251(3) 0.250000 0.9344(3) 0.0400(7) Uani 1 2 d S T P . .
O1 O 0.6886(3) 0.250000 0.8498(2) 0.0573(8) Uani 1 2 d S T P . .
O2 O 0.4770(3) 0.250000 0.8835(3) 0.0656(9) Uani 1 2 d S T P . .
O3 O 0.7083(3) 0.250000 1.0667(2) 0.0616(8) Uani 1 2 d S T P . .
O4 O 1.0031(4) 0.1289(7) 0.9358(3) 0.0648(11) Uani 0.5 1 d . . P A -1
H4C H 1.032808 0.079775 0.862397 0.097 Uiso 0.5 1 d R U P A -1
H4D H 0.897433 0.079774 0.916160 0.097 Uiso 0.5 1 d R U P A -1


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.314(4) . ?
C1 N4 1.386(4) . ?
C1 C6 1.424(4) . ?
C2 N2 1.338(4) . ?
C2 C6 1.405(4) . ?
C2 C3 1.406(4) . ?
C3 C4 1.347(4) . ?
C3 H3A 0.9300 . ?
C4 N3 1.373(4) . ?
C4 N6 1.398(4) . ?
C5 N5 1.322(4) . ?
C5 N3 1.354(4) . ?
C5 C6 1.409(4) . ?
N1 N2 1.369(3) . ?
N2 H2 0.8600 . ?
N3 H3 0.8600 . ?
N4 H4A 0.8215 . ?
N4 H4B 0.8983 . ?
N4 H4B 0.8983 4_565 ?
N5 H5A 0.8600 . ?
N5 H5B 0.8600 . ?
N6 N7 1.251(4) . ?
N7 N8 1.104(4) . ?
N9 O2 1.232(3) . ?
N9 O3 1.234(3) . ?
N9 O1 1.239(3) . ?
O4 H4C 0.9600 . ?
O4 H4D 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 N4 120.7(3) . . ?
N1 C1 C6 111.3(2) . . ?
N4 C1 C6 128.1(3) . . ?
N2 C2 C6 106.1(3) . . ?
N2 C2 C3 131.0(3) . . ?
C6 C2 C3 122.9(3) . . ?
C4 C3 C2 115.5(3) . . ?
C4 C3 H3A 122.2 . . ?
C2 C3 H3A 122.2 . . ?
C3 C4 N3 122.1(3) . . ?
C3 C4 N6 127.2(3) . . ?
N3 C4 N6 110.7(2) . . ?
N5 C5 N3 118.0(3) . . ?
N5 C5 C6 126.0(3) . . ?
N3 C5 C6 116.0(3) . . ?
C2 C6 C5 119.1(3) . . ?
C2 C6 C1 104.5(2) . . ?
C5 C6 C1 136.4(3) . . ?
C1 N1 N2 105.4(2) . . ?
C2 N2 N1 112.8(2) . . ?
C2 N2 H2 123.6 . . ?
N1 N2 H2 123.6 . . ?
C5 N3 C4 124.4(2) . . ?
C5 N3 H3 117.8 . . ?
C4 N3 H3 117.8 . . ?
C1 N4 H4A 112.1 . . ?
C1 N4 H4B 108.2 . . ?
H4A N4 H4B 111.1 . . ?
C1 N4 H4B 108.19(9) . 4_565 ?
H4A N4 H4B 111.1 . 4_565 ?
H4B N4 H4B 105.9 . 4_565 ?
C5 N5 H5A 120.0 . . ?
C5 N5 H5B 120.0 . . ?
H5A N5 H5B 120.0 . . ?
N7 N6 C4 113.9(2) . . ?
N8 N7 N6 172.5(3) . . ?
O2 N9 O3 120.7(3) . . ?
O2 N9 O1 118.5(3) . . ?
O3 N9 O1 120.8(3) . . ?
H4C O4 H4D 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N2 C2 C3 C4 180.000(1) . . . . ?
C6 C2 C3 C4 0.000(1) . . . . ?
C2 C3 C4 N3 0.000(1) . . . . ?
C2 C3 C4 N6 180.000(1) . . . . ?
N2 C2 C6 C5 180.000(1) . . . . ?
C3 C2 C6 C5 0.000(1) . . . . ?
N2 C2 C6 C1 0.000(1) . . . . ?
C3 C2 C6 C1 180.000(1) . . . . ?
N5 C5 C6 C2 180.000(1) . . . . ?
N3 C5 C6 C2 0.000(1) . . . . ?
N5 C5 C6 C1 0.000(1) . . . . ?
N3 C5 C6 C1 180.000(1) . . . . ?
N1 C1 C6 C2 0.000(1) . . . . ?
N4 C1 C6 C2 180.000(1) . . . . ?
N1 C1 C6 C5 180.000(1) . . . . ?
N4 C1 C6 C5 0.000(1) . . . . ?
N4 C1 N1 N2 180.000(0) . . . . ?
C6 C1 N1 N2 0.000(1) . . . . ?
C6 C2 N2 N1 0.000(1) . . . . ?
C3 C2 N2 N1 180.000(1) . . . . ?
C1 N1 N2 C2 0.000(1) . . . . ?
N5 C5 N3 C4 180.000(1) . . . . ?
C6 C5 N3 C4 0.000(1) . . . . ?
C3 C4 N3 C5 0.000(1) . . . . ?
N6 C4 N3 C5 180.000(1) . . . . ?
C3 C4 N6 N7 0.000(1) . . . . ?
N3 C4 N6 N7 180.000(1) . . . . ?

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
C3 H3A O1 0.93 2.45 3.147(4) 131.7 . yes
N2 H2 N9 0.86 2.61 3.455(4) 168.6 . yes
N2 H2 O1 0.86 2.28 2.993(3) 140.2 . yes
N2 H2 O2 0.86 2.21 3.040(3) 163.3 . yes
N3 H3 O3 0.86 1.97 2.830(3) 179.7 1_554 yes
N4 H4A N6 0.82 2.66 3.445(4) 159.3 1_455 yes
N4 H4A O3 0.82 2.51 2.985(3) 118.3 1_454 yes
N4 H4B O4^a 0.90 2.26 2.904(4) 128.7 1_454 yes
N4 H4B O4^a 0.90 2.02 2.897(4) 165.0 3_656 yes
N5 H5A O2 0.86 2.07 2.929(3) 178.2 1_554 yes
N5 H5B O4^a 0.86 2.08 2.875(4) 153.5 1_454 yes
N5 H5B O4^a 0.86 2.08 2.875(4) 153.5 4_464 yes
O4^a H4C^a N4 0.96 2.36 2.897(4) 114.7 3_656 yes
O4^a H4C^a N8 0.96 2.39 3.116(5) 132.2 . yes
O4^a H4D^a O1 0.96 2.06 2.753(4) 127.3 . yes

_refine_diff_density_max         0.291
_refine_diff_density_min         -0.205
_refine_diff_density_rms         0.047

