# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 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_A5ME_0m
_database_code_depnum_ccdc_archive 'CCDC 2189319'
loop_
_audit_author_name
_audit_author_address
'Dongshuai Su'
;Beijing Institute of Technology
China
;
_audit_update_record             
;
2022-07-11 deposited with the CCDC.	2023-07-24 downloaded from the CCDC.
;
_audit_creation_date             2022-01-07
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.09.19 svn.r3010 for OlexSys, GUI svn.r4874)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C7 H6 N8 O6'
_chemical_formula_sum            'C7 H6 N8 O6'
_chemical_formula_weight         298.20
_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 0.0033 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'
O O 0.0106 0.0060 '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'

_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+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'

_cell_length_a                   5.2481(12)
_cell_length_b                   14.898(3)
_cell_length_c                   15.184(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1187.2(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2701
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.44
_cell_measurement_theta_min      2.68
_shelx_estimated_absorpt_T_max   0.980
_shelx_estimated_absorpt_T_min   0.974
_exptl_absorpt_coefficient_mu    0.147
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.668
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.14
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0315
_diffrn_reflns_av_unetI/netI     0.0376
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            6870
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.437
_diffrn_reflns_theta_min         1.915
_diffrn_ambient_temperature      296(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.994
_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_standards_number         0
_reflns_Friedel_coverage         0.681
_reflns_Friedel_fraction_full    0.986
_reflns_Friedel_fraction_max     0.971
_reflns_number_gt                2291
_reflns_number_total             2675
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.214
_refine_diff_density_min         -0.166
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details 
;
 Flack x determined using 781 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.1(8)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.935
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         2675
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0466
_refine_ls_R_factor_gt           0.0378
_refine_ls_restrained_S_all      0.935
_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)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1142
_refine_ls_wR_factor_ref         0.1298
_refine_special_details          ?
_olex2_refinement_description    
;
1. Others
 Fixed Uiso: H2(0.086) H12(0.086) H3(0.086) H7A(0.081) H7B(0.081) H7C(0.081)
 Fixed X: H2(0.837295) H12(0.538582) H3(0.687726) H7A(0.503963) H7B(0.370938)
 H7C(0.634426)
 Fixed Y: H2(0.522162) H12(0.522127) H3(0.467203) H7A(0.131476) H7B(0.062688)
 H7C(0.104648)
 Fixed Z: H2(0.554805) H12(0.554937) H3(0.483536) H7A(0.668517) H7B(0.731686)
 H7C(0.757586)
;
_atom_sites_solution_hydrogens   geom
_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
O1 O -0.2359(6) 0.1843(2) 0.94218(18) 0.0799(9) Uani 1 1 d . . . . .
O2 O -0.2058(5) 0.32871(18) 0.94190(17) 0.0709(7) Uani 1 1 d . . . . .
O3 O 0.3058(6) 0.45593(15) 0.87443(18) 0.0743(9) Uani 1 1 d . . . . .
O4 O -0.0118(7) 0.44905(18) 0.7891(2) 0.1037(13) Uani 1 1 d . . . . .
O5 O 1.1712(4) 0.24857(14) 0.56413(14) 0.0552(6) Uani 1 1 d . . . . .
O6 O 1.1183(6) 0.37710(17) 0.50018(14) 0.0640(7) Uani 1 1 d . . . . .
N1 N -0.1388(5) 0.2541(2) 0.91822(16) 0.0513(6) Uani 1 1 d . . . . .
N2 N 0.1607(5) 0.41528(14) 0.82889(15) 0.0432(6) Uani 1 1 d . . . . .
N3 N 1.0599(5) 0.31951(17) 0.55274(15) 0.0435(6) Uani 1 1 d . . . . .
N4 N 0.1565(5) 0.17064(15) 0.83053(15) 0.0416(6) Uani 1 1 d . . . . .
N5 N 0.3425(5) 0.18994(13) 0.77356(14) 0.0369(5) Uani 1 1 d . . . . .
N6 N 0.7619(5) 0.27785(14) 0.66757(14) 0.0364(5) Uani 1 1 d . . . . .
N7 N 0.4986(5) 0.39812(13) 0.66152(14) 0.0375(5) Uani 1 1 d . . . . .
N8 N 0.6882(5) 0.40759(13) 0.60245(14) 0.0381(5) Uani 1 1 d . . . . .
C1 C 0.0713(6) 0.24902(17) 0.85723(16) 0.0372(6) Uani 1 1 d . . . . .
C2 C 0.2014(5) 0.31998(15) 0.81793(15) 0.0333(5) Uani 1 1 d . . . . .
C3 C 0.3777(5) 0.27974(15) 0.76308(15) 0.0321(5) Uani 1 1 d . . . . .
C4 C 0.5504(5) 0.31908(15) 0.69872(15) 0.0314(5) Uani 1 1 d . . . . .
C5 C 0.8379(5) 0.33556(16) 0.60790(16) 0.0347(6) Uani 1 1 d . . . . .
C6 C 0.6879(8) 0.48669(19) 0.5438(2) 0.0573(9) Uani 1 1 d . . . . .
H2 H 0.837295 0.522162 0.554805 0.086 Uiso 1 1 calc R U . . .
H12 H 0.538582 0.522127 0.554937 0.086 Uiso 1 1 calc R U . . .
H3 H 0.687726 0.467203 0.483536 0.086 Uiso 1 1 calc R U . . .
C7 C 0.4744(7) 0.11576(16) 0.7290(2) 0.0542(8) Uani 1 1 d . . . . .
H7A H 0.503963 0.131476 0.668517 0.081 Uiso 1 1 calc R U . . .
H7B H 0.370938 0.062688 0.731686 0.081 Uiso 1 1 calc R U . . .
H7C H 0.634426 0.104648 0.757586 0.081 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 1.213(3) . ?
O2 N1 1.220(3) . ?
O3 N2 1.194(3) . ?
O4 N2 1.199(4) . ?
O5 N3 1.220(3) . ?
O6 N3 1.211(3) . ?
N1 C1 1.442(4) . ?
N2 C2 1.445(3) . ?
N3 C5 1.455(4) . ?
N4 N5 1.335(3) . ?
N4 C1 1.314(3) . ?
N5 C3 1.360(3) . ?
N5 C7 1.469(3) . ?
N6 C4 1.354(3) . ?
N6 C5 1.311(3) . ?
N7 N8 1.347(3) . ?
N7 C4 1.334(3) . ?
N8 C5 1.332(3) . ?
N8 C6 1.477(3) . ?
C1 C2 1.393(4) . ?
C2 C3 1.382(4) . ?
C3 C4 1.456(4) . ?
C6 H2 0.9600 . ?
C6 H12 0.9600 . ?
C6 H3 0.9600 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 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
O1 N1 O2 124.8(3) . . ?
O1 N1 C1 118.0(3) . . ?
O2 N1 C1 117.2(3) . . ?
O3 N2 O4 124.1(3) . . ?
O3 N2 C2 118.1(3) . . ?
O4 N2 C2 117.8(3) . . ?
O5 N3 C5 116.4(2) . . ?
O6 N3 O5 125.9(3) . . ?
O6 N3 C5 117.7(3) . . ?
C1 N4 N5 104.9(2) . . ?
N4 N5 C3 112.8(2) . . ?
N4 N5 C7 118.7(2) . . ?
C3 N5 C7 128.5(2) . . ?
C5 N6 C4 101.1(2) . . ?
C4 N7 N8 103.0(2) . . ?
N7 N8 C6 119.0(2) . . ?
C5 N8 N7 108.04(19) . . ?
C5 N8 C6 132.9(3) . . ?
N4 C1 N1 120.3(2) . . ?
N4 C1 C2 112.1(2) . . ?
C2 C1 N1 127.6(2) . . ?
C1 C2 N2 128.6(2) . . ?
C3 C2 N2 126.5(2) . . ?
C3 C2 C1 104.9(2) . . ?
N5 C3 C2 105.4(2) . . ?
N5 C3 C4 124.0(2) . . ?
C2 C3 C4 130.3(2) . . ?
N6 C4 C3 124.2(2) . . ?
N7 C4 N6 114.8(2) . . ?
N7 C4 C3 120.9(2) . . ?
N6 C5 N3 122.3(2) . . ?
N6 C5 N8 113.1(2) . . ?
N8 C5 N3 124.7(2) . . ?
N8 C6 H2 109.5 . . ?
N8 C6 H12 109.5 . . ?
N8 C6 H3 109.5 . . ?
H2 C6 H12 109.5 . . ?
H2 C6 H3 109.5 . . ?
H12 C6 H3 109.5 . . ?
N5 C7 H7A 109.5 . . ?
N5 C7 H7B 109.5 . . ?
N5 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 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
O1 N1 C1 N4 -1.5(4) . . . . ?
O1 N1 C1 C2 176.4(3) . . . . ?
O2 N1 C1 N4 178.6(3) . . . . ?
O2 N1 C1 C2 -3.5(4) . . . . ?
O3 N2 C2 C1 103.1(4) . . . . ?
O3 N2 C2 C3 -78.8(3) . . . . ?
O4 N2 C2 C1 -79.5(4) . . . . ?
O4 N2 C2 C3 98.7(4) . . . . ?
O5 N3 C5 N6 0.8(4) . . . . ?
O5 N3 C5 N8 -177.5(2) . . . . ?
O6 N3 C5 N6 -179.0(3) . . . . ?
O6 N3 C5 N8 2.7(4) . . . . ?
N1 C1 C2 N2 0.7(5) . . . . ?
N1 C1 C2 C3 -177.8(2) . . . . ?
N2 C2 C3 N5 -178.8(2) . . . . ?
N2 C2 C3 C4 -5.2(4) . . . . ?
N4 N5 C3 C2 0.3(3) . . . . ?
N4 N5 C3 C4 -173.8(2) . . . . ?
N4 C1 C2 N2 178.7(2) . . . . ?
N4 C1 C2 C3 0.3(3) . . . . ?
N5 N4 C1 N1 178.1(2) . . . . ?
N5 N4 C1 C2 -0.1(3) . . . . ?
N5 C3 C4 N6 -27.5(4) . . . . ?
N5 C3 C4 N7 148.0(3) . . . . ?
N7 N8 C5 N3 178.1(2) . . . . ?
N7 N8 C5 N6 -0.3(3) . . . . ?
N8 N7 C4 N6 0.4(3) . . . . ?
N8 N7 C4 C3 -175.4(2) . . . . ?
C1 N4 N5 C3 -0.2(3) . . . . ?
C1 N4 N5 C7 -178.2(3) . . . . ?
C1 C2 C3 N5 -0.3(3) . . . . ?
C1 C2 C3 C4 173.2(3) . . . . ?
C2 C3 C4 N6 160.0(2) . . . . ?
C2 C3 C4 N7 -24.5(4) . . . . ?
C4 N6 C5 N3 -177.9(2) . . . . ?
C4 N6 C5 N8 0.6(3) . . . . ?
C4 N7 N8 C5 -0.1(3) . . . . ?
C4 N7 N8 C6 176.7(2) . . . . ?
C5 N6 C4 N7 -0.6(3) . . . . ?
C5 N6 C4 C3 175.1(2) . . . . ?
C6 N8 C5 N3 1.9(5) . . . . ?
C6 N8 C5 N6 -176.5(3) . . . . ?
C7 N5 C3 C2 178.1(3) . . . . ?
C7 N5 C3 C4 4.0(5) . . . . ?

_shelx_SHELXL_version_number     2016/6
_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_ame2
_database_code_depnum_ccdc_archive 'CCDC 2205892'
loop_
_audit_author_name
_audit_author_address
'Dongshuai Su'
;Beijing Institute of Technology
China
;
_audit_update_record             
;
2022-09-07 deposited with the CCDC.	2023-07-24 downloaded from the CCDC.
;
_audit_creation_date             2022-09-07
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.09.19 svn.r3010 for OlexSys, GUI svn.r4874)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C7 H6 N8 O6'
_chemical_formula_sum            'C7 H6 N8 O6'
_chemical_formula_weight         298.20
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   8.638(10)
_cell_length_b                   17.10(2)
_cell_length_c                   8.705(10)
_cell_angle_alpha                90
_cell_angle_beta                 111.112(14)
_cell_angle_gamma                90
_cell_volume                     1200(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    726
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      20.02
_cell_measurement_theta_min      2.78
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.145
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.651
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1242
_diffrn_reflns_av_unetI/netI     0.1308
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            6628
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.691
_diffrn_reflns_theta_min         2.382
_diffrn_ambient_temperature      296(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.987
_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_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1107
_reflns_number_total             2495
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.364
_refine_diff_density_min         -0.380
_refine_diff_density_rms         0.086
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.008
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         2495
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1640
_refine_ls_R_factor_gt           0.0807
_refine_ls_restrained_S_all      1.008
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1976
_refine_ls_wR_factor_ref         0.2414
_refine_special_details          ?
_olex2_refinement_description    
;
1. Others
 Fixed Uiso: H23(0.097) H24(0.097) H25(0.097) H19(0.108) H20(0.108) H21(0.108)
 Fixed X: H23(1.12424) H24(1.151391) H25(1.152553) H19(0.675426) H20(0.598009)
 H21(0.732928)
 Fixed Y: H23(0.101457) H24(0.096694) H25(0.178102) H19(0.112653)
 H20(0.031301) H21(0.037186)
 Fixed Z: H23(0.215646) H24(0.403431) H25(0.321035) H19(-0.262911) H20(-
 0.332509) H21(-0.155058)
;
_atom_sites_solution_hydrogens   geom
_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
O1 O 1.0592(5) 0.2165(2) 0.5584(5) 0.0878(12) Uani 1 1 d . . . . .
O2 O 0.8206(5) 0.2142(2) 0.5825(5) 0.0862(12) Uani 1 1 d . . . . .
O3 O 0.4787(4) 0.1347(3) 0.3737(5) 0.0887(13) Uani 1 1 d . . . . .
O4 O 0.4942(5) 0.2484(3) 0.2785(6) 0.1069(16) Uani 1 1 d . . . . .
O5 O 0.0391(4) 0.0928(3) -0.1107(5) 0.1254(19) Uani 1 1 d . . . . .
O6 O 0.0220(4) 0.0499(2) -0.3465(4) 0.0747(10) Uani 1 1 d . . . . .
N1 N 0.9143(5) 0.2017(2) 0.5087(5) 0.0622(11) Uani 1 1 d . . . . .
N2 N 0.5385(5) 0.1819(3) 0.3100(5) 0.0652(11) Uani 1 1 d . . . . .
N3 N 0.9253(4) 0.1338(2) 0.2649(4) 0.0528(10) Uani 1 1 d . . . . .
N4 N 0.8217(4) 0.1061(2) 0.1223(4) 0.0538(10) Uani 1 1 d . . . . .
N5 N 0.3713(4) 0.1028(2) -0.0091(4) 0.0542(10) Uani 1 1 d . . . . .
N6 N 0.5102(4) 0.0753(2) -0.1676(4) 0.0524(10) Uani 1 1 d . . . . .
N7 N 0.3513(4) 0.0624(2) -0.2632(4) 0.0546(10) Uani 1 1 d . . . . .
N8 N 0.0995(5) 0.0737(3) -0.2092(5) 0.0682(12) Uani 1 1 d . . . . .
C1 C 1.1036(5) 0.1269(3) 0.3046(6) 0.0645(13) Uani 1 1 d . . . . .
H23 H 1.124240 0.101457 0.215646 0.097 Uiso 1 1 calc R U . . .
H24 H 1.151391 0.096694 0.403431 0.097 Uiso 1 1 calc R U . . .
H25 H 1.152553 0.178102 0.321035 0.097 Uiso 1 1 calc R U . . .
C2 C 0.8397(5) 0.1648(2) 0.3519(5) 0.0504(11) Uani 1 1 d . . . . .
C3 C 0.6768(5) 0.1563(3) 0.2639(5) 0.0479(11) Uani 1 1 d . . . . .
C4 C 0.6691(5) 0.1203(2) 0.1193(5) 0.0471(11) Uani 1 1 d . . . . .
C5 C 0.5208(5) 0.0994(2) -0.0176(5) 0.0474(10) Uani 1 1 d . . . . .
C6 C 0.2778(5) 0.0800(3) -0.1602(5) 0.0536(12) Uani 1 1 d . . . . .
C7 C 0.6403(6) 0.0631(3) -0.2353(6) 0.0720(15) Uani 1 1 d . . . . .
H19 H 0.675426 0.112653 -0.262911 0.108 Uiso 1 1 calc R U . . .
H20 H 0.598009 0.031301 -0.332509 0.108 Uiso 1 1 calc R U . . .
H21 H 0.732928 0.037186 -0.155058 0.108 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 1.195(5) . ?
O2 N1 1.220(5) . ?
O3 N2 1.198(5) . ?
O4 N2 1.199(5) . ?
O5 N8 1.198(5) . ?
O6 N8 1.211(5) . ?
N1 C2 1.430(6) . ?
N2 C3 1.458(6) . ?
N3 N4 1.329(5) . ?
N3 C1 1.456(5) . ?
N3 C2 1.343(5) . ?
N4 C4 1.331(5) . ?
N5 C5 1.321(5) . ?
N5 C6 1.330(5) . ?
N6 N7 1.343(5) . ?
N6 C5 1.341(5) . ?
N6 C7 1.460(5) . ?
N7 C6 1.307(5) . ?
N8 C6 1.446(6) . ?
C1 H23 0.9600 . ?
C1 H24 0.9600 . ?
C1 H25 0.9600 . ?
C2 C3 1.345(6) . ?
C3 C4 1.382(6) . ?
C4 C5 1.445(6) . ?
C7 H19 0.9600 . ?
C7 H20 0.9600 . ?
C7 H21 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
O1 N1 O2 125.4(5) . . ?
O1 N1 C2 119.5(4) . . ?
O2 N1 C2 115.1(4) . . ?
O3 N2 O4 126.1(5) . . ?
O3 N2 C3 117.2(5) . . ?
O4 N2 C3 116.6(5) . . ?
N4 N3 C1 119.5(4) . . ?
N4 N3 C2 110.1(3) . . ?
C2 N3 C1 130.4(4) . . ?
N3 N4 C4 106.4(3) . . ?
C5 N5 C6 101.0(4) . . ?
N7 N6 C7 119.3(4) . . ?
C5 N6 N7 110.5(3) . . ?
C5 N6 C7 130.2(4) . . ?
C6 N7 N6 100.2(3) . . ?
O5 N8 O6 124.7(4) . . ?
O5 N8 C6 117.4(4) . . ?
O6 N8 C6 117.8(4) . . ?
N3 C1 H23 109.5 . . ?
N3 C1 H24 109.5 . . ?
N3 C1 H25 109.5 . . ?
H23 C1 H24 109.5 . . ?
H23 C1 H25 109.5 . . ?
H24 C1 H25 109.5 . . ?
N3 C2 N1 124.2(4) . . ?
N3 C2 C3 108.2(4) . . ?
C3 C2 N1 127.6(4) . . ?
C2 C3 N2 127.2(4) . . ?
C2 C3 C4 105.3(4) . . ?
C4 C3 N2 127.5(4) . . ?
N4 C4 C3 109.9(4) . . ?
N4 C4 C5 123.3(4) . . ?
C3 C4 C5 126.8(4) . . ?
N5 C5 N6 110.0(4) . . ?
N5 C5 C4 122.5(4) . . ?
N6 C5 C4 127.5(4) . . ?
N5 C6 N8 121.1(4) . . ?
N7 C6 N5 118.3(4) . . ?
N7 C6 N8 120.6(4) . . ?
N6 C7 H19 109.5 . . ?
N6 C7 H20 109.5 . . ?
N6 C7 H21 109.5 . . ?
H19 C7 H20 109.5 . . ?
H19 C7 H21 109.5 . . ?
H20 C7 H21 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
O1 N1 C2 N3 10.9(7) . . . . ?
O1 N1 C2 C3 -167.2(5) . . . . ?
O2 N1 C2 N3 -167.9(4) . . . . ?
O2 N1 C2 C3 14.0(7) . . . . ?
O3 N2 C3 C2 -95.6(6) . . . . ?
O3 N2 C3 C4 86.4(6) . . . . ?
O4 N2 C3 C2 85.1(6) . . . . ?
O4 N2 C3 C4 -92.9(6) . . . . ?
O5 N8 C6 N5 2.9(7) . . . . ?
O5 N8 C6 N7 -177.9(5) . . . . ?
O6 N8 C6 N5 -177.4(4) . . . . ?
O6 N8 C6 N7 1.8(7) . . . . ?
N1 C2 C3 N2 -1.1(8) . . . . ?
N1 C2 C3 C4 177.3(4) . . . . ?
N2 C3 C4 N4 179.7(4) . . . . ?
N2 C3 C4 C5 -0.7(7) . . . . ?
N3 N4 C4 C3 -1.1(5) . . . . ?
N3 N4 C4 C5 179.3(4) . . . . ?
N3 C2 C3 N2 -179.5(4) . . . . ?
N3 C2 C3 C4 -1.1(5) . . . . ?
N4 N3 C2 N1 -178.0(4) . . . . ?
N4 N3 C2 C3 0.5(5) . . . . ?
N4 C4 C5 N5 169.4(4) . . . . ?
N4 C4 C5 N6 -11.3(7) . . . . ?
N6 N7 C6 N5 0.0(5) . . . . ?
N6 N7 C6 N8 -179.1(4) . . . . ?
N7 N6 C5 N5 0.3(5) . . . . ?
N7 N6 C5 C4 -179.1(4) . . . . ?
C1 N3 N4 C4 -180.0(4) . . . . ?
C1 N3 C2 N1 2.4(7) . . . . ?
C1 N3 C2 C3 -179.1(4) . . . . ?
C2 N3 N4 C4 0.4(5) . . . . ?
C2 C3 C4 N4 1.4(5) . . . . ?
C2 C3 C4 C5 -179.1(4) . . . . ?
C3 C4 C5 N5 -10.1(7) . . . . ?
C3 C4 C5 N6 169.2(4) . . . . ?
C5 N5 C6 N7 0.1(5) . . . . ?
C5 N5 C6 N8 179.3(4) . . . . ?
C5 N6 N7 C6 -0.2(5) . . . . ?
C6 N5 C5 N6 -0.2(5) . . . . ?
C6 N5 C5 C4 179.2(4) . . . . ?
C7 N6 N7 C6 -179.6(4) . . . . ?
C7 N6 C5 N5 179.6(4) . . . . ?
C7 N6 C5 C4 0.2(7) . . . . ?

_shelx_SHELXL_version_number     2016/6
_olex2_submission_special_instructions 'No special instructions were received'
