# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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_cu_20210701_NLG_1_0m_4
_audit_block_doi                 10.5517/ccdc.csd.cc2hjj1m
_database_code_depnum_ccdc_archive 'CCDC 2309780'
loop_
_audit_author_name
_audit_author_address
A
;Nanjing university of science and technology
China
;
_audit_update_record             
;
2023-11-23 deposited with the CCDC.	2024-01-17 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         ?
_chemical_formula_sum            'C4 H8 N12 O2'
_chemical_formula_weight         256.22

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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'

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

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

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

_cell_length_a                   6.5961(17)
_cell_length_b                   7.3355(15)
_cell_length_c                   11.576(2)
_cell_angle_alpha                97.689(9)
_cell_angle_beta                 104.047(11)
_cell_angle_gamma                99.886(11)
_cell_volume                     526.2(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    190(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.617
_exptl_crystal_F_000             264
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    1.159
_shelx_estimated_absorpt_T_min   0.801
_shelx_estimated_absorpt_T_max   0.893
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      190(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            2062
_diffrn_reflns_av_unetI/netI     0.0294
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_limit_h_min       ?
_diffrn_reflns_limit_h_max       ?
_diffrn_reflns_limit_k_min       ?
_diffrn_reflns_limit_k_max       ?
_diffrn_reflns_limit_l_min       ?
_diffrn_reflns_limit_l_max       ?
_diffrn_reflns_theta_min         6.764
_diffrn_reflns_theta_max         72.630
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             2062
_reflns_number_gt                1862
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0649P)²+0.1617P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2062
_refine_ls_number_parameters     163
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0391
_refine_ls_R_factor_gt           0.0359
_refine_ls_wR_factor_ref         0.1040
_refine_ls_wR_factor_gt          0.1013
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_restrained_S_all      1.030
_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
O1 O 0.86517(17) 1.26750(13) 0.63650(9) 0.0298(3) Uani 1 1 d . . . . .
O2 O 0.69431(16) 1.10667(13) 0.45706(8) 0.0265(2) Uani 1 1 d . . . . .
N3 N 0.80214(18) 1.11066(16) 0.56550(10) 0.0219(3) Uani 1 1 d . . . . .
N4 N 0.5133(2) 0.48492(18) 0.23205(11) 0.0371(3) Uani 1 1 d . . . . .
H4A H 0.498106 0.362877 0.209190 0.045 Uiso 1 1 calc R U . . .
H4B H 0.461652 0.552945 0.179489 0.045 Uiso 1 1 calc R U . . .
N5 N 0.69973(19) 0.48317(16) 0.43423(10) 0.0258(3) Uani 1 1 d . . . . .
H5A H 0.696473 0.361662 0.426885 0.039 Uiso 1 1 calc R U . . .
N6 N 0.7943(2) 0.61117(17) 0.53912(11) 0.0263(3) Uani 1 1 d . . . . .
N7 N 0.65198(18) 0.75048(15) 0.39224(10) 0.0229(3) Uani 1 1 d . . . . .
H7 H 0.612297 0.839586 0.353741 0.027 Uiso 1 1 calc R U . . .
N8 N 0.4534(2) -0.07749(17) 0.19369(11) 0.0289(3) Uani 1 1 d . . . . .
N9 N 0.41018(19) 0.07534(17) 0.15391(11) 0.0280(3) Uani 1 1 d . . . . .
N10 N 0.2853(2) 0.02324(18) 0.04218(11) 0.0297(3) Uani 1 1 d . . . . .
N11 N 0.2529(2) -0.16090(18) 0.01263(11) 0.0312(3) Uani 1 1 d . . . . .
N12 N 0.3570(2) -0.22324(18) 0.10620(11) 0.0313(3) Uani 1 1 d . . . . .
C1 C 0.9744(2) 0.94982(19) 0.72259(12) 0.0226(3) Uani 1 1 d . . . . .
N1 N 1.0149(2) 0.79052(18) 0.75428(11) 0.0292(3) Uani 1 1 d . . . . .
H1A H 1.092563 0.790813 0.827794 0.035 Uiso 1 1 calc R U . . .
H1B H 0.964061 0.684120 0.701861 0.035 Uiso 1 1 calc R U . . .
N2 N 1.05216(19) 1.10690(17) 0.80255(10) 0.0266(3) Uani 1 1 d . . . . .
H2A H 1.129573 1.104694 0.875690 0.032 Uiso 1 1 calc R U . . .
H2B H 1.026761 1.214252 0.782937 0.032 Uiso 1 1 calc R U . . .
C2 C 0.8460(2) 0.94810(18) 0.59973(12) 0.0215(3) Uani 1 1 d . . . . .
C3 C 0.7651(2) 0.77379(19) 0.51210(12) 0.0214(3) Uani 1 1 d . . . . .
C4 C 0.6136(2) 0.56588(19) 0.34509(12) 0.0245(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
O1 N3 1.2605(15) . ?
O2 N3 1.2775(15) . ?
N3 C2 1.3609(17) . ?
N4 C4 1.3189(18) . ?
N5 C4 1.3254(18) . ?
N5 N6 1.3679(16) . ?
N6 C3 1.3068(18) . ?
N7 C4 1.3465(17) . ?
N7 C3 1.3788(17) . ?
N8 N9 1.3169(17) . ?
N8 N12 1.3180(17) . ?
N9 N10 1.3190(18) . ?
N10 N11 1.3150(19) . ?
N11 N12 1.3166(18) . ?
C1 N2 1.3148(18) . ?
C1 N1 1.3210(18) . ?
C1 C2 1.4653(18) . ?
C2 C3 1.4507(19) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 N3 O2 117.90(10) . . ?
O1 N3 C2 122.65(11) . . ?
O2 N3 C2 119.45(11) . . ?
C4 N5 N6 111.22(11) . . ?
C3 N6 N5 105.34(11) . . ?
C4 N7 C3 107.19(11) . . ?
N9 N8 N12 107.99(12) . . ?
N8 N9 N10 107.79(12) . . ?
N11 N10 N9 108.25(11) . . ?
N10 N11 N12 107.85(12) . . ?
N11 N12 N8 108.11(12) . . ?
N2 C1 N1 118.83(12) . . ?
N2 C1 C2 121.56(12) . . ?
N1 C1 C2 119.60(12) . . ?
N3 C2 C3 118.79(11) . . ?
N3 C2 C1 120.48(12) . . ?
C3 C2 C1 120.73(12) . . ?
N6 C3 N7 109.91(12) . . ?
N6 C3 C2 122.46(12) . . ?
N7 C3 C2 127.62(12) . . ?
N4 C4 N5 127.11(13) . . ?
N4 C4 N7 126.55(13) . . ?
N5 C4 N7 106.33(12) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C4 N5 N6 C3 -0.27(16) . . . . ?
N12 N8 N9 N10 0.61(16) . . . . ?
N8 N9 N10 N11 -0.52(16) . . . . ?
N9 N10 N11 N12 0.23(16) . . . . ?
N10 N11 N12 N8 0.15(16) . . . . ?
N9 N8 N12 N11 -0.47(16) . . . . ?
O1 N3 C2 C3 179.42(11) . . . . ?
O2 N3 C2 C3 -1.14(19) . . . . ?
O1 N3 C2 C1 -1.1(2) . . . . ?
O2 N3 C2 C1 178.30(11) . . . . ?
N2 C1 C2 N3 -0.6(2) . . . . ?
N1 C1 C2 N3 179.80(12) . . . . ?
N2 C1 C2 C3 178.84(12) . . . . ?
N1 C1 C2 C3 -0.77(19) . . . . ?
N5 N6 C3 N7 0.53(15) . . . . ?
N5 N6 C3 C2 -178.93(12) . . . . ?
C4 N7 C3 N6 -0.61(15) . . . . ?
C4 N7 C3 C2 178.82(13) . . . . ?
N3 C2 C3 N6 -177.70(12) . . . . ?
C1 C2 C3 N6 2.9(2) . . . . ?
N3 C2 C3 N7 2.9(2) . . . . ?
C1 C2 C3 N7 -176.50(12) . . . . ?
N6 N5 C4 N4 178.87(14) . . . . ?
N6 N5 C4 N7 -0.10(16) . . . . ?
C3 N7 C4 N4 -178.56(14) . . . . ?
C3 N7 C4 N5 0.42(15) . . . . ?

_refine_diff_density_max         0.281
_refine_diff_density_min         -0.251
_refine_diff_density_rms         0.048

####################################################################### 
# 
# 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
_audit_block_doi                 10.5517/ccdc.csd.cc2hjj2n
_database_code_depnum_ccdc_archive 'CCDC 2309781'
loop_
_audit_author_name
_audit_author_address
A
;Nanjing university of science and technology
China
;
_audit_update_record             
;
2023-12-04 deposited with the CCDC.	2024-01-17 downloaded from the CCDC.
;
_audit_creation_date             2023-12-04
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C4 H8 N7 O2, Cl'
_chemical_formula_sum            'C4 H8 Cl N7 O2'
_chemical_formula_weight         221.62
_chemical_absolute_configuration ?
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, z+1/2'

_cell_length_a                   9.6066(6)
_cell_length_b                   19.8590(14)
_cell_length_c                   4.6599(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     889.00(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1892
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      26.33
_cell_measurement_theta_min      2.95
_shelx_estimated_absorpt_T_max   0.979
_shelx_estimated_absorpt_T_min   0.847
_exptl_absorpt_coefficient_mu    0.419
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6775
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   'SADABS (Bruker, 2014)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'greenish green'
_exptl_crystal_colour_modifier   greenish
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.656
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             456
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0479
_diffrn_reflns_av_unetI/netI     0.0417
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       5
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_number            6900
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.363
_diffrn_reflns_theta_min         2.950
_diffrn_ambient_temperature      173.10
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.765
_reflns_Friedel_fraction_full    0.991
_reflns_Friedel_fraction_max     0.982
_reflns_number_gt                1618
_reflns_number_total             1800
_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  'olex2.refine 1.5 (Bourhis et al., 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.208
_refine_diff_density_min         -0.208
_refine_diff_density_rms         0.051
_refine_ls_abs_structure_details 
;
 Flack x determined using 627 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.26(4)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_matrix_type           full
_refine_ls_number_parameters     151
_refine_ls_number_reflns         1800
_refine_ls_number_restraints     17
_refine_ls_R_factor_all          0.0399
_refine_ls_R_factor_gt           0.0316
_refine_ls_restrained_S_all      1.072
_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)+(0.0272P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0612
_refine_ls_wR_factor_ref         0.0638
_refine_special_details          ?
_olex2_refinement_description    
;
1. Restrained distances
 N4-H4A \\sim N4-H4B \\sim N5-H5A \\sim N5-H5B \\sim N6-H6A \\sim N6-H6B
 with sigma of 0.02
 N2-H2 \\sim N3-H3
 with sigma of 0.02
;
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     iterative
_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 0.9807(3) 0.22941(16) 1.0037(7) 0.0209(7) Uani 1 1 d . . . . .
C2 C 0.8801(3) 0.13463(15) 0.8740(6) 0.0194(7) Uani 1 1 d . . . . .
C3 C 0.7841(3) 0.08760(17) 0.7386(7) 0.0201(7) Uani 1 1 d . . . . .
C4 C 0.7710(3) 0.01868(17) 0.8404(7) 0.0228(7) Uani 1 1 d . . . . .
Cl1 Cl 0.76477(7) 0.34234(4) 0.60515(19) 0.02429(19) Uani 1 1 d . . . . .
N1 N 0.9731(3) 0.11740(14) 1.0665(6) 0.0247(6) Uani 1 1 d . . . . .
N2 N 1.0329(3) 0.17779(14) 1.1493(6) 0.0252(6) Uani 1 1 d D . . . .
H2 H 1.103(4) 0.1772(18) 1.264(8) 0.030 Uiso 1 1 d DR . . . .
N3 N 0.8833(3) 0.20296(14) 0.8287(6) 0.0202(6) Uani 1 1 d D . . . .
H3 H 0.831(3) 0.2249(17) 0.712(7) 0.024 Uiso 1 1 d DR . . . .
N4 N 1.0162(3) 0.29354(16) 1.0151(7) 0.0285(7) Uani 1 1 d D . . . .
H4A H 1.071(3) 0.3079(18) 1.160(6) 0.034 Uiso 1 1 d DR . . . .
H4B H 0.954(3) 0.3218(17) 0.932(7) 0.034 Uiso 1 1 d DR . . . .
N5 N 0.8579(3) -0.00384(15) 1.0405(6) 0.0277(7) Uani 1 1 d D . . . .
H5A H 0.841(3) -0.0453(13) 1.114(8) 0.033 Uiso 1 1 d DR . . . .
H5B H 0.923(3) 0.0242(15) 1.122(8) 0.033 Uiso 1 1 d DR . . . .
N6 N 0.6751(3) -0.02280(16) 0.7402(7) 0.0323(7) Uani 1 1 d D . . . .
H6A H 0.617(3) -0.0053(18) 0.612(7) 0.039 Uiso 1 1 d DR . . . .
H6B H 0.671(4) -0.0641(13) 0.814(8) 0.039 Uiso 1 1 d DR . . . .
N7 N 0.7019(3) 0.11094(14) 0.5184(5) 0.0214(6) Uani 1 1 d . . . . .
O1 O 0.6111(2) 0.07441(11) 0.3992(5) 0.0311(6) Uani 1 1 d . . . . .
O2 O 0.7159(2) 0.17087(11) 0.4317(5) 0.0275(6) 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
C1 N2 1.328(4) . ?
C1 N3 1.348(4) . ?
C1 N4 1.320(4) . ?
C2 C3 1.456(4) . ?
C2 N1 1.312(4) . ?
C2 N3 1.374(4) . ?
C3 C4 1.454(5) . ?
C3 N7 1.375(4) . ?
C4 N5 1.329(4) . ?
C4 N6 1.321(4) . ?
N1 N2 1.384(4) . ?
N2 H2 0.86(3) . ?
N3 H3 0.86(3) . ?
N4 H4A 0.90(2) . ?
N4 H4B 0.91(2) . ?
N5 H5A 0.91(2) . ?
N5 H5B 0.92(2) . ?
N6 H6A 0.89(2) . ?
N6 H6B 0.89(2) . ?
N7 O1 1.263(3) . ?
N7 O2 1.264(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 C1 N3 105.7(3) . . ?
N4 C1 N2 128.8(3) . . ?
N4 C1 N3 125.5(3) . . ?
N1 C2 C3 124.1(3) . . ?
N1 C2 N3 110.3(3) . . ?
N3 C2 C3 125.6(3) . . ?
C4 C3 C2 121.2(3) . . ?
N7 C3 C2 118.1(3) . . ?
N7 C3 C4 120.7(3) . . ?
N5 C4 C3 119.4(3) . . ?
N6 C4 C3 122.2(3) . . ?
N6 C4 N5 118.4(3) . . ?
C2 N1 N2 104.3(3) . . ?
C1 N2 N1 111.7(3) . . ?
C1 N2 H2 129(2) . . ?
N1 N2 H2 119(2) . . ?
C1 N3 C2 107.9(3) . . ?
C1 N3 H3 126(2) . . ?
C2 N3 H3 126(2) . . ?
C1 N4 H4A 119(2) . . ?
C1 N4 H4B 114(2) . . ?
H4A N4 H4B 121(4) . . ?
C4 N5 H5A 117(2) . . ?
C4 N5 H5B 121(2) . . ?
H5A N5 H5B 121(3) . . ?
C4 N6 H6A 116(2) . . ?
C4 N6 H6B 118(3) . . ?
H6A N6 H6B 126(3) . . ?
O1 N7 C3 122.1(3) . . ?
O1 N7 O2 118.3(2) . . ?
O2 N7 C3 119.6(3) . . ?

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
N2 H2 Cl1 0.86(3) 2.26(3) 3.104(3) 168(3) 3_556
N3 H3 Cl1 0.86(3) 2.47(3) 3.169(3) 139(3) .
N4 H4A O2 0.90(2) 1.93(2) 2.819(4) 169(3) 3_556
N4 H4B Cl1 0.91(2) 2.40(3) 3.229(3) 151(3) .
N5 H5A Cl1 0.91(2) 2.45(3) 3.288(3) 154(3) 4_645
N5 H5B N1 0.92(2) 1.93(3) 2.653(4) 134(3) .
N6 H6A O1 0.89(2) 1.87(3) 2.575(4) 135(3) .
N6 H6B Cl1 0.89(2) 2.38(3) 3.224(3) 158(3) 4_645

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
C2 C3 C4 N5 -7.0(5) . . . . ?
C2 C3 C4 N6 173.1(3) . . . . ?
C2 C3 N7 O1 -176.4(3) . . . . ?
C2 C3 N7 O2 3.1(4) . . . . ?
C2 N1 N2 C1 -2.1(3) . . . . ?
C3 C2 N1 N2 -175.9(3) . . . . ?
C3 C2 N3 C1 176.6(3) . . . . ?
C4 C3 N7 O1 1.1(4) . . . . ?
C4 C3 N7 O2 -179.4(3) . . . . ?
N1 C2 C3 C4 9.3(5) . . . . ?
N1 C2 C3 N7 -173.2(3) . . . . ?
N1 C2 N3 C1 -1.1(4) . . . . ?
N2 C1 N3 C2 -0.3(4) . . . . ?
N3 C1 N2 N1 1.5(3) . . . . ?
N3 C2 C3 C4 -168.1(3) . . . . ?
N3 C2 C3 N7 9.4(4) . . . . ?
N3 C2 N1 N2 1.9(3) . . . . ?
N4 C1 N2 N1 -176.7(3) . . . . ?
N4 C1 N3 C2 178.0(3) . . . . ?
N7 C3 C4 N5 175.6(3) . . . . ?
N7 C3 C4 N6 -4.3(5) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
