# Supplementary Information (SI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 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_20230224_ys_nlg_jg_71_0m
_database_code_depnum_ccdc_archive 'CCDC 2326589'
loop_
_audit_author_name
_audit_author_address
jinganA
;Nanjing University of Science and Technology
China
;
_audit_update_record             
;
2024-01-19 deposited with the CCDC.	2024-10-07 downloaded from the CCDC.
;
_audit_creation_date             2023-02-27
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.02.24 svn.rf166f9f3 for OlexSys, GUI svn.r6725)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C5 H4 N8 O2'
_chemical_formula_sum            'C5 H4 N8 O2'
_chemical_formula_weight         208.16
_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      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                   6.3057(2)
_cell_length_b                   9.7520(3)
_cell_length_c                   13.0730(4)
_cell_angle_alpha                90
_cell_angle_beta                 94.800(2)
_cell_angle_gamma                90
_cell_volume                     801.08(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2371
_cell_measurement_temperature    198.00
_cell_measurement_theta_max      67.867
_cell_measurement_theta_min      5.667
_shelx_estimated_absorpt_T_max   0.898
_shelx_estimated_absorpt_T_min   0.877
_exptl_absorpt_coefficient_mu    1.220
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.6671
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1129 before and 0.0515 after correction.
The Ratio of minimum to maximum transmission is 0.8858.
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    1.726
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             424
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.09
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0528
_diffrn_reflns_av_unetI/netI     0.0302
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            7173
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.015
_diffrn_reflns_theta_min         5.667
_diffrn_ambient_temperature      198.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_source_current           1.1
_diffrn_source_power             0.05500000000000001
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1185
_reflns_number_total             1452
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_refine_diff_density_max         0.192
_refine_diff_density_min         -0.170
_refine_diff_density_rms         0.040
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         1452
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0431
_refine_ls_R_factor_gt           0.0314
_refine_ls_restrained_S_all      1.084
_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)+(0.0371P)²+0.1482P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0771
_refine_ls_wR_factor_ref         0.0825
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups
2. Uiso/Uaniso restraints and constraints
C5A \\sim C5B: within 2A with sigma of 0.004 and sigma for terminal atoms of
0.008 within 2A
3. Others
 Sof(C4B)=Sof(H4BA)=Sof(H4BB)=Sof(C5B)=Sof(H5BA)=Sof(H5BB)=1-FVAR(1)
 Sof(C4A)=Sof(H4AA)=Sof(H4AB)=Sof(C5A)=Sof(H5AA)=Sof(H5AB)=FVAR(1)
4.a Secondary CH2 refined with riding coordinates:
 C4A(H4AA,H4AB), C4B(H4BA,H4BB), C5A(H5AA,H5AB), C5B(H5BA,H5BB)
;
_atom_sites_solution_hydrogens   geom
_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 0.6458(2) 0.49935(15) 0.66174(11) 0.0305(3) Uani 1 1 d . . . . .
C2 C 0.5259(2) 0.34365(15) 0.56984(11) 0.0293(3) Uani 1 1 d . . . . .
C3 C 0.4698(2) 0.23498(15) 0.49732(11) 0.0310(3) Uani 1 1 d . . . . .
C4A C 0.1087(8) 0.2175(6) 0.5655(4) 0.0443(15) Uani 0.439(8) 1 d . . P A 1
H4AA H 0.029509 0.288430 0.523770 0.053 Uiso 0.439(8) 1 calc R U P A 1
H4AB H 0.009527 0.141877 0.578401 0.053 Uiso 0.439(8) 1 calc R U P A 1
C4B C 0.1886(7) 0.1606(4) 0.6075(3) 0.0425(12) Uani 0.561(8) 1 d . . P A 2
H4BA H 0.268723 0.100734 0.658197 0.051 Uiso 0.561(8) 1 calc R U P A 2
H4BB H 0.041284 0.125564 0.595607 0.051 Uiso 0.561(8) 1 calc R U P A 2
C5A C 0.200(3) 0.2765(16) 0.6636(14) 0.041(2) Uani 0.439(8) 1 d . U P A 1
H5AA H 0.246463 0.202166 0.711895 0.049 Uiso 0.439(8) 1 calc R U P A 1
H5AB H 0.090552 0.331805 0.695148 0.049 Uiso 0.439(8) 1 calc R U P A 1
C5B C 0.188(2) 0.3106(12) 0.6465(11) 0.049(2) Uani 0.561(8) 1 d . U P A 2
H5BA H 0.082554 0.364950 0.603433 0.058 Uiso 0.561(8) 1 calc R U P A 2
H5BB H 0.147921 0.312601 0.718045 0.058 Uiso 0.561(8) 1 calc R U P A 2
N1 N 0.7866(2) 0.60757(13) 0.70390(10) 0.0363(3) Uani 1 1 d . . . . .
N2 N 0.4683(2) 0.47094(14) 0.70366(11) 0.0366(3) Uani 1 1 d . . . . .
N3 N 0.69238(18) 0.42654(12) 0.57974(9) 0.0313(3) Uani 1 1 d . . . . .
N4 N 0.39210(18) 0.36844(13) 0.64229(10) 0.0325(3) Uani 1 1 d . . . . .
N5 N 0.5582(2) 0.18849(16) 0.41729(11) 0.0468(4) Uani 1 1 d . . . . .
N6 N 0.4287(2) 0.08496(15) 0.38014(11) 0.0454(4) Uani 1 1 d . . . . .
N7 N 0.2697(2) 0.06899(15) 0.43538(11) 0.0459(4) Uani 1 1 d . . . . .
N8 N 0.2933(2) 0.16391(14) 0.50956(11) 0.0412(3) Uani 1 1 d . . . . .
O1 O 0.72852(19) 0.67422(12) 0.77518(9) 0.0461(3) Uani 1 1 d . . . . .
O2 O 0.9529(2) 0.62362(14) 0.66480(11) 0.0552(4) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.4575(19) . ?
C1 N2 1.316(2) . ?
C1 N3 1.3389(19) . ?
C2 C3 1.446(2) . ?
C2 N3 1.3226(19) . ?
C2 N4 1.3421(19) . ?
C3 N5 1.307(2) . ?
C3 N8 1.332(2) . ?
C4A H4AA 0.9900 . ?
C4A H4AB 0.9900 . ?
C4A C5A 1.48(2) . ?
C4A N8 1.518(4) . ?
C4B H4BA 0.9900 . ?
C4B H4BB 0.9900 . ?
C4B C5B 1.549(15) . ?
C4B N8 1.489(3) . ?
C5A H5AA 0.9900 . ?
C5A H5AB 0.9900 . ?
C5A N4 1.553(16) . ?
C5B H5BA 0.9900 . ?
C5B H5BB 0.9900 . ?
C5B N4 1.408(15) . ?
N1 O1 1.2175(18) . ?
N1 O2 1.2145(18) . ?
N2 N4 1.3451(18) . ?
N5 N6 1.362(2) . ?
N6 N7 1.294(2) . ?
N7 N8 1.3400(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
N2 C1 N1 120.49(13) . . ?
N2 C1 N3 118.23(13) . . ?
N3 C1 N1 121.28(13) . . ?
N3 C2 C3 131.35(13) . . ?
N3 C2 N4 111.20(13) . . ?
N4 C2 C3 117.45(13) . . ?
N5 C3 C2 132.97(14) . . ?
N5 C3 N8 109.40(14) . . ?
N8 C3 C2 117.62(13) . . ?
H4AA C4A H4AB 108.5 . . ?
C5A C4A H4AA 110.3 . . ?
C5A C4A H4AB 110.3 . . ?
C5A C4A N8 107.1(8) . . ?
N8 C4A H4AA 110.3 . . ?
N8 C4A H4AB 110.3 . . ?
H4BA C4B H4BB 108.7 . . ?
C5B C4B H4BA 110.5 . . ?
C5B C4B H4BB 110.5 . . ?
N8 C4B H4BA 110.5 . . ?
N8 C4B H4BB 110.5 . . ?
N8 C4B C5B 106.0(6) . . ?
C4A C5A H5AA 109.9 . . ?
C4A C5A H5AB 109.9 . . ?
C4A C5A N4 108.7(11) . . ?
H5AA C5A H5AB 108.3 . . ?
N4 C5A H5AA 109.9 . . ?
N4 C5A H5AB 109.9 . . ?
C4B C5B H5BA 109.7 . . ?
C4B C5B H5BB 109.7 . . ?
H5BA C5B H5BB 108.2 . . ?
N4 C5B C4B 109.8(10) . . ?
N4 C5B H5BA 109.7 . . ?
N4 C5B H5BB 109.7 . . ?
O1 N1 C1 117.59(13) . . ?
O2 N1 C1 117.02(13) . . ?
O2 N1 O1 125.39(14) . . ?
C1 N2 N4 100.49(12) . . ?
C2 N3 C1 100.19(12) . . ?
C2 N4 C5A 124.7(8) . . ?
C2 N4 C5B 125.8(7) . . ?
C2 N4 N2 109.90(12) . . ?
N2 N4 C5A 124.6(8) . . ?
N2 N4 C5B 123.8(7) . . ?
C3 N5 N6 105.05(13) . . ?
N7 N6 N5 111.09(13) . . ?
N6 N7 N8 106.04(13) . . ?
C3 N8 C4A 124.1(2) . . ?
C3 N8 C4B 123.33(17) . . ?
C3 N8 N7 108.42(13) . . ?
N7 N8 C4A 122.9(2) . . ?
N7 N8 C4B 125.23(17) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 N2 N4 C2 -0.07(16) . . . . ?
C1 N2 N4 C5A 170.2(6) . . . . ?
C1 N2 N4 C5B -172.1(5) . . . . ?
C2 C3 N5 N6 -179.63(16) . . . . ?
C2 C3 N8 C4A 23.5(4) . . . . ?
C2 C3 N8 C4B -18.8(3) . . . . ?
C2 C3 N8 N7 180.00(13) . . . . ?
C3 C2 N3 C1 -179.19(15) . . . . ?
C3 C2 N4 C5A 9.1(6) . . . . ?
C3 C2 N4 C5B -8.8(6) . . . . ?
C3 C2 N4 N2 179.38(12) . . . . ?
C3 N5 N6 N7 -0.3(2) . . . . ?
C4A C5A N4 C2 -34.0(11) . . . . ?
C4A C5A N4 N2 157.2(6) . . . . ?
C4B C5B N4 C2 35.8(10) . . . . ?
C4B C5B N4 N2 -153.4(5) . . . . ?
C5A C4A N8 C3 -47.8(8) . . . . ?
C5A C4A N8 N7 159.0(6) . . . . ?
C5B C4B N8 C3 43.8(7) . . . . ?
C5B C4B N8 N7 -158.1(6) . . . . ?
N1 C1 N2 N4 -179.96(12) . . . . ?
N1 C1 N3 C2 179.95(12) . . . . ?
N2 C1 N1 O1 -3.7(2) . . . . ?
N2 C1 N1 O2 176.29(14) . . . . ?
N2 C1 N3 C2 -0.17(17) . . . . ?
N3 C1 N1 O1 176.23(13) . . . . ?
N3 C1 N1 O2 -3.8(2) . . . . ?
N3 C1 N2 N4 0.15(17) . . . . ?
N3 C2 C3 N5 -3.5(3) . . . . ?
N3 C2 C3 N8 176.96(15) . . . . ?
N3 C2 N4 C5A -170.3(6) . . . . ?
N3 C2 N4 C5B 171.8(5) . . . . ?
N3 C2 N4 N2 -0.02(17) . . . . ?
N4 C2 C3 N5 177.27(16) . . . . ?
N4 C2 C3 N8 -2.3(2) . . . . ?
N4 C2 N3 C1 0.10(15) . . . . ?
N5 C3 N8 C4A -156.1(4) . . . . ?
N5 C3 N8 C4B 161.6(3) . . . . ?
N5 C3 N8 N7 0.34(19) . . . . ?
N5 N6 N7 N8 0.5(2) . . . . ?
N6 N7 N8 C3 -0.50(19) . . . . ?
N6 N7 N8 C4A 156.3(4) . . . . ?
N6 N7 N8 C4B -161.3(3) . . . . ?
N8 C3 N5 N6 -0.05(19) . . . . ?
N8 C4A C5A N4 46.3(10) . . . . ?
N8 C4B C5B N4 -47.8(9) . . . . ?

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

data_mo_20221215_zm_nlg_jg_65_0m
_database_code_depnum_ccdc_archive 'CCDC 2326592'
loop_
_audit_author_name
_audit_author_address
jinganA
;Nanjing University of Science and Technology
China
;
_audit_update_record             
;
2024-01-19 deposited with the CCDC.	2024-10-07 downloaded from the CCDC.
;
_audit_creation_date             2022-12-16
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        123
_chemical_formula_moiety         'C6 H6 N8 O2'
_chemical_formula_sum            'C6 H6 N8 O2'
_chemical_formula_weight         222.19
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/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                   14.5643(12)
_cell_length_b                   9.3620(8)
_cell_length_c                   15.0278(11)
_cell_angle_alpha                90
_cell_angle_beta                 117.847(3)
_cell_angle_gamma                90
_cell_volume                     1811.8(3)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    2067
_cell_measurement_temperature    193.00
_cell_measurement_theta_max      24.52
_cell_measurement_theta_min      2.66
_shelx_estimated_absorpt_T_max   0.986
_shelx_estimated_absorpt_T_min   0.983
_exptl_absorpt_coefficient_mu    0.130
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6504
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1310 before and 0.0651 after correction.
The Ratio of minimum to maximum transmission is 0.8723.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.629
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             912
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0839
_diffrn_reflns_av_unetI/netI     0.0658
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            19688
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.496
_diffrn_reflns_theta_min         2.661
_diffrn_ambient_temperature      193.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2455
_reflns_number_total             4141
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.305
_refine_diff_density_min         -0.250
_refine_diff_density_rms         0.056
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     316
_refine_ls_number_reflns         4141
_refine_ls_number_restraints     7
_refine_ls_R_factor_all          0.1051
_refine_ls_R_factor_gt           0.0556
_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)+(0.0658P)²+0.5659P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1333
_refine_ls_wR_factor_ref         0.1605
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups
2. Restrained distances
 C8A-H9B
 1.6 with sigma of 0.002
 N12-C7A \\sim N12-C7
 with sigma of 0.02
 C9-C7A \\sim C9-C7
 with sigma of 0.04
 C9-C8 \\sim C9-C8A
 with sigma of 0.02
 N12-C8 \\sim N12-C8A
 with sigma of 0.04
 C7A-C8 \\sim C7-C8A
 with sigma of 0.02
 C9-H9A \\sim C9-H9B
 with sigma of 0.02
3. Others
 Sof(C7)=Sof(H7A)=Sof(H7B)=Sof(C8A)=Sof(H8AA)=Sof(H8AB)=1-FVAR(1)
 Sof(C7A)=Sof(H7AA)=Sof(H7AB)=Sof(C8)=Sof(H8A)=Sof(H8B)=FVAR(1)
4.a Secondary CH2 refined with riding coordinates:
 C7A(H7AA,H7AB), C7(H7A,H7B), C8A(H8AA,H8AB), C8(H8A,H8B), C1(H1A,H1B), C2(H2A,
 H2B), C3(H3A,H3B)
;
_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
O3 O 0.70637(19) 0.3205(3) 0.22746(18) 0.0585(6) Uani 1 1 d . . . . .
O4 O 0.83290(19) 0.3737(3) 0.19795(16) 0.0572(6) Uani 1 1 d . . . . .
C7A C 0.7980(5) 0.6726(7) 0.5150(4) 0.0398(16) Uani 0.790(9) 1 d D . P A 1
H7AA H 0.745793 0.610369 0.520214 0.048 Uiso 0.790(9) 1 calc R U P A 1
H7AB H 0.764719 0.765542 0.486861 0.048 Uiso 0.790(9) 1 calc R U P A 1
C7 C 0.820(2) 0.6259(19) 0.5369(14) 0.047(7) Uani 0.210(9) 1 d D . P A 2
H7A H 0.866975 0.562229 0.591802 0.056 Uiso 0.210(9) 1 calc R U P A 2
H7B H 0.747256 0.604930 0.522090 0.056 Uiso 0.210(9) 1 calc R U P A 2
C8A C 0.8457(10) 0.7806(18) 0.5660(12) 0.054(6) Uani 0.210(9) 1 d D . P A 2
H8AA H 0.818402 0.837100 0.503094 0.065 Uiso 0.210(9) 1 calc R U P A 2
H8AB H 0.806905 0.810765 0.602066 0.065 Uiso 0.210(9) 1 calc R U P A 2
C8 C 0.8882(3) 0.6954(4) 0.6185(3) 0.0378(12) Uani 0.790(9) 1 d D . P A 1
H8A H 0.860608 0.706057 0.667083 0.045 Uiso 0.790(9) 1 calc R U P A 1
H8B H 0.932252 0.608707 0.637540 0.045 Uiso 0.790(9) 1 calc R U P A 1
N9 N 0.78509(19) 0.3848(3) 0.24364(17) 0.0397(6) Uani 1 1 d . . . . .
C9 C 0.9549(3) 0.8217(4) 0.6283(3) 0.0500(9) Uani 1 1 d D . . . .
H9A H 1.009(3) 0.827(4) 0.695(2) 0.081(13) Uiso 1 1 d D . . . .
H9B H 0.924(2) 0.913(2) 0.609(3) 0.092(15) Uiso 1 1 d D . . . .
N10 N 0.91413(16) 0.5545(2) 0.35865(15) 0.0300(5) Uani 1 1 d . . . . .
C10 C 1.0001(2) 0.7323(3) 0.49119(18) 0.0288(6) Uani 1 1 d . . . . .
N11 N 0.77092(18) 0.5103(3) 0.37696(16) 0.0397(6) Uani 1 1 d . . . . .
C11 C 0.91753(19) 0.6314(3) 0.43475(17) 0.0267(5) Uani 1 1 d . . . . .
N12 N 0.83287(17) 0.6058(3) 0.44642(15) 0.0343(5) Uani 1 1 d D . . . .
C12 C 0.8246(2) 0.4862(3) 0.32814(18) 0.0311(6) Uani 1 1 d . . . . .
N13 N 1.07525(18) 0.7615(3) 0.46831(16) 0.0395(6) Uani 1 1 d . . . . .
N14 N 1.1354(2) 0.8608(3) 0.53661(19) 0.0495(7) Uani 1 1 d . . . . .
N15 N 1.0993(2) 0.8900(3) 0.59883(19) 0.0486(7) Uani 1 1 d . . . . .
N16 N 1.01410(18) 0.8104(3) 0.57137(16) 0.0365(6) Uani 1 1 d . . . . .
N1 N 0.2138(2) 0.5511(3) 0.2091(2) 0.0443(6) Uani 1 1 d . . . . .
O1 O 0.16029(18) 0.5798(3) 0.24933(18) 0.0608(7) Uani 1 1 d . . . . .
C1 C 0.6523(2) 0.2300(4) 0.4824(2) 0.0454(8) Uani 1 1 d . . . . .
H1A H 0.702176 0.152953 0.519507 0.055 Uiso 1 1 calc R U . . .
H1B H 0.692465 0.318006 0.488408 0.055 Uiso 1 1 calc R U . . .
N2 N 0.36889(17) 0.4312(2) 0.23069(16) 0.0332(5) Uani 1 1 d . . . . .
C2 C 0.5923(2) 0.1893(3) 0.3736(2) 0.0437(7) Uani 1 1 d . . . . .
H2A H 0.541460 0.114713 0.367434 0.052 Uiso 1 1 calc R U . . .
H2B H 0.641209 0.145676 0.352743 0.052 Uiso 1 1 calc R U . . .
O2 O 0.19463(19) 0.5832(3) 0.12353(16) 0.0613(7) Uani 1 1 d . . . . .
C3 C 0.5346(2) 0.3073(4) 0.3005(2) 0.0415(7) Uani 1 1 d . . . . .
H3A H 0.583721 0.386013 0.309945 0.050 Uiso 1 1 calc R U . . .
H3B H 0.508745 0.270642 0.231106 0.050 Uiso 1 1 calc R U . . .
N3 N 0.44629(16) 0.3651(2) 0.31118(15) 0.0291(5) Uani 1 1 d . . . . .
N4 N 0.33723(17) 0.4376(2) 0.36495(16) 0.0315(5) Uani 1 1 d . . . . .
C4 C 0.42615(19) 0.3706(3) 0.38998(18) 0.0275(5) Uani 1 1 d . . . . .
C5 C 0.4891(2) 0.3147(3) 0.49022(18) 0.0282(6) Uani 1 1 d . . . . .
N5 N 0.46121(18) 0.3229(3) 0.56196(16) 0.0363(6) Uani 1 1 d . . . . .
C6 C 0.3081(2) 0.4704(3) 0.26882(19) 0.0325(6) Uani 1 1 d . . . . .
N6 N 0.58342(17) 0.2542(2) 0.52776(16) 0.0345(5) Uani 1 1 d . . . . .
N7 N 0.6139(2) 0.2215(3) 0.62443(16) 0.0432(6) Uani 1 1 d . . . . .
N8 N 0.5399(2) 0.2624(3) 0.64407(17) 0.0422(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
O3 N9 1.215(3) . ?
O4 N9 1.189(3) . ?
C7A H7AA 0.9900 . ?
C7A H7AB 0.9900 . ?
C7A C8 1.510(6) . ?
C7A N12 1.483(5) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C8A 1.510(16) . ?
C7 N12 1.471(15) . ?
C8A H8AA 0.9900 . ?
C8A H8AB 0.9900 . ?
C8A C9 1.471(13) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C9 1.494(5) . ?
N9 C12 1.470(3) . ?
C9 H9A 0.95(3) . ?
C9 H9B 0.95(3) . ?
C9 N16 1.475(4) . ?
N10 C11 1.332(3) . ?
N10 C12 1.327(3) . ?
C10 C11 1.451(4) . ?
C10 N13 1.320(3) . ?
C10 N16 1.341(3) . ?
N11 N12 1.350(3) . ?
N11 C12 1.318(3) . ?
C11 N12 1.346(3) . ?
N13 N14 1.358(3) . ?
N14 N15 1.298(3) . ?
N15 N16 1.337(3) . ?
N1 O1 1.218(3) . ?
N1 O2 1.220(3) . ?
N1 C6 1.453(3) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C1 C2 1.499(4) . ?
C1 N6 1.471(4) . ?
N2 N3 1.357(3) . ?
N2 C6 1.312(3) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C3 1.508(4) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 N3 1.471(3) . ?
N3 C4 1.347(3) . ?
N4 C4 1.326(3) . ?
N4 C6 1.337(3) . ?
C4 C5 1.447(3) . ?
C5 N5 1.320(3) . ?
C5 N6 1.342(3) . ?
N5 N8 1.355(3) . ?
N6 N7 1.341(3) . ?
N7 N8 1.301(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
H7AA C7A H7AB 108.0 . . ?
C8 C7A H7AA 109.4 . . ?
C8 C7A H7AB 109.4 . . ?
N12 C7A H7AA 109.4 . . ?
N12 C7A H7AB 109.4 . . ?
N12 C7A C8 111.1(4) . . ?
H7A C7 H7B 108.8 . . ?
C8A C7 H7A 110.7 . . ?
C8A C7 H7B 110.7 . . ?
N12 C7 H7A 110.7 . . ?
N12 C7 H7B 110.7 . . ?
N12 C7 C8A 105.4(12) . . ?
C7 C8A H8AA 107.5 . . ?
C7 C8A H8AB 107.5 . . ?
H8AA C8A H8AB 107.0 . . ?
C9 C8A C7 119.1(16) . . ?
C9 C8A H8AA 107.5 . . ?
C9 C8A H8AB 107.5 . . ?
C7A C8 H8A 108.5 . . ?
C7A C8 H8B 108.5 . . ?
H8A C8 H8B 107.5 . . ?
C9 C8 C7A 115.3(4) . . ?
C9 C8 H8A 108.5 . . ?
C9 C8 H8B 108.5 . . ?
O3 N9 C12 116.4(2) . . ?
O4 N9 O3 126.4(3) . . ?
O4 N9 C12 117.2(2) . . ?
C8A C9 H9A 144(3) . . ?
C8A C9 H9B 79.7(10) . . ?
C8A C9 N16 111.3(6) . . ?
C8 C9 H9A 109(2) . . ?
C8 C9 H9B 119.3(13) . . ?
H9A C9 H9B 109(3) . . ?
N16 C9 C8 114.5(3) . . ?
N16 C9 H9A 102(2) . . ?
N16 C9 H9B 102(2) . . ?
C12 N10 C11 101.2(2) . . ?
N13 C10 C11 123.0(2) . . ?
N13 C10 N16 109.0(2) . . ?
N16 C10 C11 128.1(2) . . ?
C12 N11 N12 100.8(2) . . ?
N10 C11 C10 122.8(2) . . ?
N10 C11 N12 110.3(2) . . ?
N12 C11 C10 126.8(2) . . ?
N11 N12 C7A 119.6(3) . . ?
N11 N12 C7 118.0(8) . . ?
C11 N12 C7A 130.4(3) . . ?
C11 N12 C7 128.4(10) . . ?
C11 N12 N11 109.8(2) . . ?
N10 C12 N9 122.3(2) . . ?
N11 C12 N9 119.8(2) . . ?
N11 C12 N10 117.9(2) . . ?
C10 N13 N14 105.4(2) . . ?
N15 N14 N13 110.7(2) . . ?
N14 N15 N16 106.9(2) . . ?
C10 N16 C9 132.5(2) . . ?
N15 N16 C9 119.4(2) . . ?
N15 N16 C10 108.1(2) . . ?
O1 N1 O2 125.8(3) . . ?
O1 N1 C6 116.6(2) . . ?
O2 N1 C6 117.6(3) . . ?
H1A C1 H1B 108.0 . . ?
C2 C1 H1A 109.3 . . ?
C2 C1 H1B 109.3 . . ?
N6 C1 H1A 109.3 . . ?
N6 C1 H1B 109.3 . . ?
N6 C1 C2 111.6(2) . . ?
C6 N2 N3 100.79(19) . . ?
C1 C2 H2A 108.1 . . ?
C1 C2 H2B 108.1 . . ?
C1 C2 C3 116.8(3) . . ?
H2A C2 H2B 107.3 . . ?
C3 C2 H2A 108.1 . . ?
C3 C2 H2B 108.1 . . ?
C2 C3 H3A 108.7 . . ?
C2 C3 H3B 108.7 . . ?
H3A C3 H3B 107.6 . . ?
N3 C3 C2 114.1(2) . . ?
N3 C3 H3A 108.7 . . ?
N3 C3 H3B 108.7 . . ?
N2 N3 C3 118.3(2) . . ?
C4 N3 N2 109.6(2) . . ?
C4 N3 C3 132.1(2) . . ?
C4 N4 C6 100.9(2) . . ?
N3 C4 C5 127.5(2) . . ?
N4 C4 N3 110.7(2) . . ?
N4 C4 C5 121.8(2) . . ?
N5 C5 C4 122.8(2) . . ?
N5 C5 N6 109.0(2) . . ?
N6 C5 C4 128.1(2) . . ?
C5 N5 N8 105.5(2) . . ?
N2 C6 N1 120.8(2) . . ?
N2 C6 N4 118.0(2) . . ?
N4 C6 N1 121.2(2) . . ?
C5 N6 C1 131.0(2) . . ?
N7 N6 C1 121.0(2) . . ?
N7 N6 C5 107.9(2) . . ?
N8 N7 N6 106.8(2) . . ?
N7 N8 N5 110.8(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
O3 N9 C12 N10 174.5(2) . . . . ?
O3 N9 C12 N11 -4.8(4) . . . . ?
O4 N9 C12 N10 -5.5(4) . . . . ?
O4 N9 C12 N11 175.2(3) . . . . ?
C7A C8 C9 N16 -67.0(5) . . . . ?
C7 C8A C9 N16 70.1(15) . . . . ?
C8A C7 N12 N11 -148.0(11) . . . . ?
C8A C7 N12 C11 56(2) . . . . ?
C8A C9 N16 C10 -24.4(9) . . . . ?
C8A C9 N16 N15 155.0(8) . . . . ?
C8 C7A N12 N11 144.2(4) . . . . ?
C8 C7A N12 C11 -41.4(7) . . . . ?
C8 C9 N16 C10 22.4(5) . . . . ?
C8 C9 N16 N15 -158.1(3) . . . . ?
N10 C11 N12 C7A -175.0(4) . . . . ?
N10 C11 N12 C7 157.3(10) . . . . ?
N10 C11 N12 N11 -0.2(3) . . . . ?
C10 C11 N12 C7A 2.0(5) . . . . ?
C10 C11 N12 C7 -25.7(11) . . . . ?
C10 C11 N12 N11 176.8(2) . . . . ?
C10 N13 N14 N15 0.6(3) . . . . ?
C11 N10 C12 N9 -179.8(2) . . . . ?
C11 N10 C12 N11 -0.5(3) . . . . ?
C11 C10 N13 N14 179.1(2) . . . . ?
C11 C10 N16 C9 0.2(5) . . . . ?
C11 C10 N16 N15 -179.3(3) . . . . ?
N12 C7A C8 C9 78.4(6) . . . . ?
N12 C7 C8A C9 -84.7(19) . . . . ?
N12 N11 C12 N9 179.7(2) . . . . ?
N12 N11 C12 N10 0.4(3) . . . . ?
C12 N10 C11 C10 -176.8(2) . . . . ?
C12 N10 C11 N12 0.3(3) . . . . ?
C12 N11 N12 C7A 175.4(3) . . . . ?
C12 N11 N12 C7 -160.2(11) . . . . ?
C12 N11 N12 C11 -0.1(3) . . . . ?
N13 C10 C11 N10 3.7(4) . . . . ?
N13 C10 C11 N12 -172.9(3) . . . . ?
N13 C10 N16 C9 179.7(3) . . . . ?
N13 C10 N16 N15 0.2(3) . . . . ?
N13 N14 N15 N16 -0.4(3) . . . . ?
N14 N15 N16 C9 -179.4(3) . . . . ?
N14 N15 N16 C10 0.2(3) . . . . ?
N16 C10 C11 N10 -176.8(2) . . . . ?
N16 C10 C11 N12 6.6(4) . . . . ?
N16 C10 N13 N14 -0.4(3) . . . . ?
O1 N1 C6 N2 178.0(3) . . . . ?
O1 N1 C6 N4 -4.0(4) . . . . ?
C1 C2 C3 N3 -68.2(3) . . . . ?
C1 N6 N7 N8 176.3(3) . . . . ?
N2 N3 C4 N4 0.3(3) . . . . ?
N2 N3 C4 C5 -179.2(2) . . . . ?
C2 C1 N6 C5 -37.9(4) . . . . ?
C2 C1 N6 N7 146.3(3) . . . . ?
C2 C3 N3 N2 -156.7(2) . . . . ?
C2 C3 N3 C4 25.8(4) . . . . ?
O2 N1 C6 N2 -1.5(4) . . . . ?
O2 N1 C6 N4 176.5(3) . . . . ?
C3 N3 C4 N4 178.0(3) . . . . ?
C3 N3 C4 C5 -1.5(5) . . . . ?
N3 N2 C6 N1 178.1(2) . . . . ?
N3 N2 C6 N4 0.1(3) . . . . ?
N3 C4 C5 N5 -178.5(3) . . . . ?
N3 C4 C5 N6 4.7(4) . . . . ?
N4 C4 C5 N5 2.1(4) . . . . ?
N4 C4 C5 N6 -174.8(3) . . . . ?
C4 N4 C6 N1 -177.9(2) . . . . ?
C4 N4 C6 N2 0.1(3) . . . . ?
C4 C5 N5 N8 -178.9(2) . . . . ?
C4 C5 N6 C1 2.2(5) . . . . ?
C4 C5 N6 N7 178.4(3) . . . . ?
C5 N5 N8 N7 1.2(3) . . . . ?
C5 N6 N7 N8 -0.4(3) . . . . ?
N5 C5 N6 C1 -175.0(3) . . . . ?
N5 C5 N6 N7 1.2(3) . . . . ?
C6 N2 N3 C3 -178.3(2) . . . . ?
C6 N2 N3 C4 -0.3(3) . . . . ?
C6 N4 C4 N3 -0.2(3) . . . . ?
C6 N4 C4 C5 179.3(2) . . . . ?
N6 C1 C2 C3 75.3(3) . . . . ?
N6 C5 N5 N8 -1.5(3) . . . . ?
N6 N7 N8 N5 -0.5(3) . . . . ?

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

data_cu_20240418_wq_nlg_jg18_0m
_database_code_depnum_ccdc_archive 'CCDC 2356448'
loop_
_audit_author_name
_audit_author_address
jinganA
;Nanjing University of Science and Technology
China
;
_audit_update_record             
;
2024-05-20 deposited with the CCDC.	2024-10-07 downloaded from the CCDC.
;
_audit_creation_date             2024-04-19
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C7 H7 N7 O2'
_chemical_formula_sum            'C7 H7 N7 O2'
_chemical_formula_weight         221.20
_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 0.0181 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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   6.7579(3)
_cell_length_b                   8.4422(4)
_cell_length_c                   16.3524(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     932.93(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4673
_cell_measurement_temperature    223.00
_cell_measurement_theta_max      68.021
_cell_measurement_theta_min      5.899
_shelx_estimated_absorpt_T_max   0.902
_shelx_estimated_absorpt_T_min   0.875
_exptl_absorpt_coefficient_mu    1.052
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.6521
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1574 before and 0.0614 after correction.
The Ratio of minimum to maximum transmission is 0.8659.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.575
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             456
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0510
_diffrn_reflns_av_unetI/netI     0.0312
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            8704
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.338
_diffrn_reflns_theta_min         5.898
_diffrn_ambient_temperature      223.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.995
_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                   ?
_diffrn_source_current           1.1
_diffrn_source_power             0.05500000000000001
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.672
_reflns_Friedel_fraction_full    0.991
_reflns_Friedel_fraction_max     0.990
_reflns_number_gt                1588
_reflns_number_total             1700
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.395
_refine_diff_density_min         -0.210
_refine_diff_density_rms         0.049
_refine_ls_abs_structure_details 
;
 Flack x determined using 624 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.12(12)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         1700
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0442
_refine_ls_R_factor_gt           0.0378
_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)+(0.0596P)²+0.2180P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0986
_refine_ls_wR_factor_ref         0.1013
_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:
 C5(H5A,H5B), C6(H6A,H6B), C7(H7A,H7B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1)
;
_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
O1 O 0.5224(5) 0.6032(3) 0.73919(13) 0.0660(8) Uani 1 1 d . . . . .
O2 O 0.5426(3) 0.7866(3) 0.64744(13) 0.0495(6) Uani 1 1 d . . . . .
N1 N 0.5020(3) 0.6516(3) 0.66877(14) 0.0400(5) Uani 1 1 d . . . . .
N2 N 0.3255(4) 0.3129(3) 0.55789(15) 0.0459(6) Uani 1 1 d . . . . .
N3 N 0.3424(4) 0.4235(3) 0.49822(14) 0.0373(5) Uani 1 1 d . . . . .
N4 N 0.3847(3) 0.8461(3) 0.47823(14) 0.0368(5) Uani 1 1 d . . . . .
N5 N 0.4304(4) 0.9135(3) 0.40455(17) 0.0481(7) Uani 1 1 d . . . . .
N6 N 0.5028(4) 0.8092(4) 0.35488(15) 0.0490(7) Uani 1 1 d . . . . .
N7 N 0.5047(3) 0.6708(3) 0.39443(13) 0.0384(6) Uani 1 1 d . . . . .
C1 C 0.3804(4) 0.3865(4) 0.62577(18) 0.0415(7) Uani 1 1 d . . . . .
H1 H 0.383654 0.339499 0.677878 0.050 Uiso 1 1 calc R U . . .
C2 C 0.4323(4) 0.5417(3) 0.60950(16) 0.0341(6) Uani 1 1 d . . . . .
C3 C 0.4053(3) 0.5644(3) 0.52627(16) 0.0308(6) Uani 1 1 d . . . . .
C4 C 0.4325(3) 0.6953(3) 0.46948(15) 0.0309(5) Uani 1 1 d . . . . .
C5 C 0.2738(5) 0.3871(4) 0.41516(19) 0.0516(8) Uani 1 1 d . . . . .
H5A H 0.169382 0.462400 0.400330 0.062 Uiso 1 1 calc R U . . .
H5B H 0.215348 0.280891 0.415029 0.062 Uiso 1 1 calc R U . . .
C6 C 0.4330(5) 0.3936(4) 0.3513(2) 0.0550(8) Uani 1 1 d . . . . .
H6A H 0.370100 0.409668 0.297942 0.066 Uiso 1 1 calc R U . . .
H6B H 0.499286 0.290349 0.349751 0.066 Uiso 1 1 calc R U . . .
C7 C 0.5879(5) 0.5193(4) 0.3625(2) 0.0517(8) Uani 1 1 d . . . . .
H7A H 0.688757 0.480525 0.400648 0.062 Uiso 1 1 calc R U . . .
H7B H 0.652612 0.539478 0.309923 0.062 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 N1 1.230(3) . ?
O2 N1 1.223(3) . ?
N1 C2 1.422(4) . ?
N2 N3 1.355(3) . ?
N2 C1 1.325(4) . ?
N3 C3 1.344(4) . ?
N3 C5 1.468(4) . ?
N4 N5 1.368(3) . ?
N4 C4 1.321(4) . ?
N5 N6 1.294(4) . ?
N6 N7 1.336(4) . ?
N7 C4 1.337(3) . ?
N7 C7 1.491(4) . ?
C1 H1 0.9400 . ?
C1 C2 1.382(4) . ?
C2 C3 1.386(4) . ?
C3 C4 1.455(4) . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 C6 1.501(5) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 C7 1.502(5) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?

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 N1 C2 117.3(2) . . ?
O2 N1 O1 123.5(2) . . ?
O2 N1 C2 119.2(2) . . ?
C1 N2 N3 104.9(2) . . ?
N2 N3 C5 119.7(2) . . ?
C3 N3 N2 113.0(2) . . ?
C3 N3 C5 126.9(2) . . ?
C4 N4 N5 104.5(2) . . ?
N6 N5 N4 110.8(2) . . ?
N5 N6 N7 107.2(2) . . ?
N6 N7 C4 107.8(2) . . ?
N6 N7 C7 125.8(2) . . ?
C4 N7 C7 126.2(3) . . ?
N2 C1 H1 124.6 . . ?
N2 C1 C2 110.7(3) . . ?
C2 C1 H1 124.6 . . ?
C1 C2 N1 124.8(3) . . ?
C1 C2 C3 106.7(3) . . ?
C3 C2 N1 128.5(3) . . ?
N3 C3 C2 104.7(2) . . ?
N3 C3 C4 119.6(2) . . ?
C2 C3 C4 135.7(3) . . ?
N4 C4 N7 109.7(2) . . ?
N4 C4 C3 129.2(2) . . ?
N7 C4 C3 121.0(2) . . ?
N3 C5 H5A 108.7 . . ?
N3 C5 H5B 108.7 . . ?
N3 C5 C6 114.2(3) . . ?
H5A C5 H5B 107.6 . . ?
C6 C5 H5A 108.7 . . ?
C6 C5 H5B 108.7 . . ?
C5 C6 H6A 108.3 . . ?
C5 C6 H6B 108.3 . . ?
C5 C6 C7 116.1(3) . . ?
H6A C6 H6B 107.4 . . ?
C7 C6 H6A 108.3 . . ?
C7 C6 H6B 108.3 . . ?
N7 C7 C6 112.7(3) . . ?
N7 C7 H7A 109.0 . . ?
N7 C7 H7B 109.0 . . ?
C6 C7 H7A 109.0 . . ?
C6 C7 H7B 109.0 . . ?
H7A C7 H7B 107.8 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 N1 C2 C1 2.0(4) . . . . ?
O1 N1 C2 C3 -176.9(3) . . . . ?
O2 N1 C2 C1 -179.6(3) . . . . ?
O2 N1 C2 C3 1.4(4) . . . . ?
N1 C2 C3 N3 178.4(2) . . . . ?
N1 C2 C3 C4 -0.2(5) . . . . ?
N2 N3 C3 C2 0.6(3) . . . . ?
N2 N3 C3 C4 179.5(2) . . . . ?
N2 N3 C5 C6 -118.9(3) . . . . ?
N2 C1 C2 N1 -178.6(2) . . . . ?
N2 C1 C2 C3 0.6(3) . . . . ?
N3 N2 C1 C2 -0.2(3) . . . . ?
N3 C3 C4 N4 137.9(3) . . . . ?
N3 C3 C4 N7 -37.8(3) . . . . ?
N3 C5 C6 C7 -36.1(4) . . . . ?
N4 N5 N6 N7 0.5(3) . . . . ?
N5 N4 C4 N7 0.3(3) . . . . ?
N5 N4 C4 C3 -175.9(2) . . . . ?
N5 N6 N7 C4 -0.4(3) . . . . ?
N5 N6 N7 C7 -175.9(2) . . . . ?
N6 N7 C4 N4 0.1(3) . . . . ?
N6 N7 C4 C3 176.6(2) . . . . ?
N6 N7 C7 C6 -115.9(3) . . . . ?
C1 N2 N3 C3 -0.3(3) . . . . ?
C1 N2 N3 C5 -173.9(3) . . . . ?
C1 C2 C3 N3 -0.7(3) . . . . ?
C1 C2 C3 C4 -179.3(3) . . . . ?
C2 C3 C4 N4 -43.6(4) . . . . ?
C2 C3 C4 N7 140.7(3) . . . . ?
C3 N3 C5 C6 68.4(4) . . . . ?
C4 N4 N5 N6 -0.5(3) . . . . ?
C4 N7 C7 C6 69.4(4) . . . . ?
C5 N3 C3 C2 173.6(3) . . . . ?
C5 N3 C3 C4 -7.4(4) . . . . ?
C5 C6 C7 N7 -38.0(4) . . . . ?
C7 N7 C4 N4 175.6(2) . . . . ?
C7 N7 C4 C3 -7.9(4) . . . . ?

_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_cu_20240508_wq_jg23_0m
_database_code_depnum_ccdc_archive 'CCDC 2356449'
loop_
_audit_author_name
_audit_author_address
jinganA
;Nanjing University of Science and Technology
China
;
_audit_update_record             
;
2024-05-20 deposited with the CCDC.	2024-10-07 downloaded from the CCDC.
;
_audit_creation_date             2024-05-10
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C6 H5 N7 O2'
_chemical_formula_sum            'C6 H5 N7 O2'
_chemical_formula_weight         207.17
_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 0.0181 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      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                   6.3809(6)
_cell_length_b                   10.3716(8)
_cell_length_c                   12.1362(10)
_cell_angle_alpha                90
_cell_angle_beta                 91.201(6)
_cell_angle_gamma                90
_cell_volume                     803.00(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2285
_cell_measurement_temperature    233.00
_cell_measurement_theta_max      67.858
_cell_measurement_theta_min      5.612
_shelx_estimated_absorpt_T_max   0.891
_shelx_estimated_absorpt_T_min   0.872
_exptl_absorpt_coefficient_mu    1.176
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.6632
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1226 before and 0.0731 after correction.
The Ratio of minimum to maximum transmission is 0.8806.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.714
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             424
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_av_unetI/netI     0.0892
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            8695
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.251
_diffrn_reflns_theta_min         5.611
_diffrn_ambient_temperature      233.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.992
_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                   ?
_diffrn_source_current           1.1
_diffrn_source_power             0.05500000000000001
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                6427
_reflns_number_total             8695
_reflns_special_details          
;
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.367
_refine_diff_density_min         -0.410
_refine_diff_density_rms         0.091
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     137
_refine_ls_number_reflns         8695
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0789
_refine_ls_R_factor_gt           0.0575
_refine_ls_restrained_S_all      1.039
_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)+(0.0883P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1583
_refine_ls_wR_factor_ref         0.1739
_refine_special_details          
;
 Refined as a 2-component twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.502(11)
 0.498(11)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
3.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C2(H2A,H2B)
3.b Aromatic/amide H refined with riding coordinates:
 C6(H6)
;
_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
O1 O 0.2467(4) 0.6840(2) 0.4689(2) 0.0434(7) Uani 1 1 d . . . . .
O2 O 0.3321(5) 0.8561(2) 0.3790(2) 0.0543(9) Uani 1 1 d . . . . .
N1 N 0.7136(4) 0.5212(2) 0.7105(2) 0.0269(6) Uani 1 1 d . . . . .
N2 N 0.6226(5) 0.4172(2) 0.7555(2) 0.0331(7) Uani 1 1 d . . . . .
N3 N 0.4317(5) 0.4158(3) 0.7162(2) 0.0353(7) Uani 1 1 d . . . . .
N4 N 0.3951(4) 0.5155(3) 0.6461(2) 0.0324(7) Uani 1 1 d . . . . .
N5 N 0.8274(4) 0.7444(2) 0.6175(2) 0.0275(6) Uani 1 1 d . . . . .
N6 N 0.8753(5) 0.8553(2) 0.5645(2) 0.0351(7) Uani 1 1 d . . . . .
N7 N 0.3675(5) 0.7725(3) 0.4485(2) 0.0359(7) Uani 1 1 d . . . . .
C1 C 0.9361(5) 0.5524(3) 0.7182(3) 0.0329(8) Uani 1 1 d . . . . .
H1A H 1.010951 0.510391 0.658271 0.039 Uiso 1 1 calc R U . . .
H1B H 0.995681 0.521799 0.788500 0.039 Uiso 1 1 calc R U . . .
C2 C 0.9587(5) 0.6976(3) 0.7098(3) 0.0315(8) Uani 1 1 d . . . . .
H2A H 0.914902 0.738168 0.778583 0.038 Uiso 1 1 calc R U . . .
H2B H 1.105604 0.720269 0.697900 0.038 Uiso 1 1 calc R U . . .
C3 C 0.6387(5) 0.6958(3) 0.5881(3) 0.0258(7) Uani 1 1 d . . . . .
C4 C 0.5733(5) 0.5796(3) 0.6437(3) 0.0263(7) Uani 1 1 d . . . . .
C5 C 0.5615(5) 0.7804(3) 0.5080(3) 0.0303(8) Uani 1 1 d . . . . .
C6 C 0.7138(6) 0.8757(3) 0.4975(3) 0.0349(8) Uani 1 1 d . . . . .
H6 H 0.702550 0.945794 0.448619 0.042 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 N7 1.227(4) . ?
O2 N7 1.228(4) . ?
N1 N2 1.347(4) . ?
N1 C1 1.457(4) . ?
N1 C4 1.339(4) . ?
N2 N3 1.299(4) . ?
N3 N4 1.356(4) . ?
N4 C4 1.318(4) . ?
N5 N6 1.356(4) . ?
N5 C2 1.468(4) . ?
N5 C3 1.346(4) . ?
N6 C6 1.317(5) . ?
N7 C5 1.422(5) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 C2 1.517(4) . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C3 C4 1.448(5) . ?
C3 C5 1.392(4) . ?
C5 C6 1.394(5) . ?
C6 H6 0.9400 . ?

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 N1 C1 125.4(3) . . ?
C4 N1 N2 108.6(3) . . ?
C4 N1 C1 125.2(3) . . ?
N3 N2 N1 105.6(3) . . ?
N2 N3 N4 111.7(3) . . ?
C4 N4 N3 105.1(3) . . ?
N6 N5 C2 120.8(3) . . ?
C3 N5 N6 113.7(3) . . ?
C3 N5 C2 124.9(3) . . ?
C6 N6 N5 104.4(3) . . ?
O1 N7 O2 124.0(3) . . ?
O1 N7 C5 119.0(3) . . ?
O2 N7 C5 117.0(3) . . ?
N1 C1 H1A 110.1 . . ?
N1 C1 H1B 110.1 . . ?
N1 C1 C2 108.0(3) . . ?
H1A C1 H1B 108.4 . . ?
C2 C1 H1A 110.1 . . ?
C2 C1 H1B 110.1 . . ?
N5 C2 C1 109.0(3) . . ?
N5 C2 H2A 109.9 . . ?
N5 C2 H2B 109.9 . . ?
C1 C2 H2A 109.9 . . ?
C1 C2 H2B 109.9 . . ?
H2A C2 H2B 108.3 . . ?
N5 C3 C4 117.0(3) . . ?
N5 C3 C5 104.5(3) . . ?
C5 C3 C4 138.5(3) . . ?
N1 C4 C3 117.5(3) . . ?
N4 C4 N1 109.0(3) . . ?
N4 C4 C3 133.5(3) . . ?
C3 C5 N7 127.6(3) . . ?
C3 C5 C6 105.9(3) . . ?
C6 C5 N7 126.5(3) . . ?
N6 C6 C5 111.6(3) . . ?
N6 C6 H6 124.2 . . ?
C5 C6 H6 124.2 . . ?

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
O1 N7 C5 C3 1.7(5) . . . . ?
O1 N7 C5 C6 -178.2(3) . . . . ?
O2 N7 C5 C3 -178.2(3) . . . . ?
O2 N7 C5 C6 1.9(5) . . . . ?
N1 N2 N3 N4 0.4(4) . . . . ?
N1 C1 C2 N5 -46.8(4) . . . . ?
N2 N1 C1 C2 -152.2(3) . . . . ?
N2 N1 C4 N4 0.5(4) . . . . ?
N2 N1 C4 C3 178.9(3) . . . . ?
N2 N3 N4 C4 -0.1(4) . . . . ?
N3 N4 C4 N1 -0.2(3) . . . . ?
N3 N4 C4 C3 -178.3(3) . . . . ?
N5 N6 C6 C5 0.9(4) . . . . ?
N5 C3 C4 N1 -7.4(4) . . . . ?
N5 C3 C4 N4 170.6(3) . . . . ?
N5 C3 C5 N7 179.2(3) . . . . ?
N5 C3 C5 C6 -0.9(4) . . . . ?
N6 N5 C2 C1 -154.0(3) . . . . ?
N6 N5 C3 C4 -178.0(3) . . . . ?
N6 N5 C3 C5 1.6(4) . . . . ?
N7 C5 C6 N6 179.9(3) . . . . ?
C1 N1 N2 N3 -170.9(3) . . . . ?
C1 N1 C4 N4 170.9(3) . . . . ?
C1 N1 C4 C3 -10.7(5) . . . . ?
C2 N5 N6 C6 -172.4(3) . . . . ?
C2 N5 C3 C4 -7.7(5) . . . . ?
C2 N5 C3 C5 171.9(3) . . . . ?
C3 N5 N6 C6 -1.6(4) . . . . ?
C3 N5 C2 C1 36.3(4) . . . . ?
C3 C5 C6 N6 0.0(4) . . . . ?
C4 N1 N2 N3 -0.5(3) . . . . ?
C4 N1 C1 C2 39.0(4) . . . . ?
C4 C3 C5 N7 -1.4(6) . . . . ?
C4 C3 C5 C6 178.6(4) . . . . ?
C5 C3 C4 N1 173.2(4) . . . . ?
C5 C3 C4 N4 -8.8(7) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.502(11)
2 0.498(11)

