# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry A.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_NLG_0413_3_0m_4
_database_code_depnum_ccdc_archive 'CCDC 2097303'
loop_
_audit_author_name
_audit_author_address
'Yongxing Tang'
;Nanjing University of Science and Technology
China
;
_audit_update_record             
;
2021-07-19 deposited with the CCDC.	2021-09-13 downloaded from the CCDC.
;
_audit_creation_method           
;
FinalCif V69 by Daniel Kratzert, Freiburg 2019,
https://github.com/dkratzert/FinalCif
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_sum            'C6 H8 N10 O4'
_chemical_formula_moiety         ?
_chemical_formula_weight         284.22
_chemical_melting_point          ?
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'
_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+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-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                   21.60(2)
_cell_length_b                   4.493(4)
_cell_length_c                   12.608(12)
_cell_angle_alpha                90
_cell_angle_beta                 122.59(2)
_cell_angle_gamma                90
_cell_volume                     1031.2(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    170(2)
_cell_measurement_reflns_used    475
_cell_measurement_theta_min      4.2215
_cell_measurement_theta_max      50.0005
_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_recrystallization_method ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.831
_exptl_crystal_F_000             584
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.861
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.493357
_exptl_absorpt_correction_T_max  0.750111
_exptl_absorpt_process_details   
;
TWINABS - Bruker AXS scaling for twinned crystals - Version 2012/1: Krause, L.,
Herbst-Irmer, R., Sheldrick G.M. & Stalke D., J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_special_details   ?
_shelx_estimated_absorpt_T_min   0.847
_shelx_estimated_absorpt_T_max   0.919
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_special_details           ?
_diffrn_ambient_temperature      170(2)
_diffrn_ambient_environment      ?
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          ?
_diffrn_source                   ?
_diffrn_source_type              ?
_diffrn_source_voltage           69.86
_diffrn_source_current           3.57
_diffrn_detector                 ?
_diffrn_detector_type            'Bruker PHOTON II'
_diffrn_detector_area_resol_mean ?
_diffrn_measurement_device       ?
_diffrn_measurement_device_type  'Bruker D8 VENTURE Metaljet PHOTON II'
_diffrn_measurement_method       ?
_diffrn_measurement_specimen_support ?
_diffrn_reflns_number            851
_diffrn_reflns_av_unetI/netI     0.0567
_diffrn_reflns_av_R_equivalents  0.0874
_diffrn_reflns_theta_min         4.226
_diffrn_reflns_theta_max         51.385
_diffrn_reflns_theta_full        51.385
_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_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.991
_reflns_number_total             851
_reflns_number_gt                614
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_computing_data_collection       'Bruker BIS V6.2.12/2019-08-12'
_computing_cell_refinement       'SAINT V8.40A'
_computing_data_reduction        'SAINT V8.40A'
_computing_structure_solution    'SHELXT 2014/5'
_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)+(0.1355P)²+10.7606P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         851
_refine_ls_number_parameters     92
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1209
_refine_ls_R_factor_gt           0.0944
_refine_ls_wR_factor_ref         0.2716
_refine_ls_wR_factor_gt          0.2613
_refine_ls_goodness_of_fit_ref   1.112
_refine_ls_restrained_S_all      1.112
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.486
_refine_diff_density_min         -0.368
_refine_diff_density_rms         0.112
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.011(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0137 0.0067 '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 0.0241 0.0134 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0389 0.0241 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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_
_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 0.2546(2) 0.4847(11) 0.5726(4) 0.0384(15) Uani 1 1 d . . . . .
N1 N 0.4751(3) 0.6252(13) 0.7677(5) 0.0270(15) Uani 1 1 d . . . . .
C1 C 0.3616(3) 0.7079(14) 0.7114(6) 0.0248(16) Uani 1 1 d . . . . .
C2 C 0.4040(3) 0.5491(15) 0.6797(5) 0.0243(16) Uani 1 1 d . . . . .
N4 N 0.3873(3) 0.3549(12) 0.5889(5) 0.0324(16) Uani 1 1 d . . . . .
H4A H 0.422417 0.270789 0.583899 0.039 Uiso 1 1 calc R U . . .
H4B H 0.341038 0.310137 0.533552 0.039 Uiso 1 1 calc R U . . .
N3 N 0.2867(3) 0.6802(13) 0.6544(5) 0.0290(15) Uani 1 1 d . . . . .
N2 N 0.4787(3) 0.8634(12) 0.8467(5) 0.0279(15) Uani 1 1 d . . . . .
C3 C 0.4105(3) 0.8983(15) 0.8163(5) 0.0244(16) Uani 1 1 d . . . . .
N5 N 0.3926(3) 1.0836(13) 0.8775(5) 0.0331(16) Uani 1 1 d . . . . .
H5A H 0.426911 1.188923 0.940921 0.040 Uiso 1 1 calc R U . . .
H5B H 0.346448 1.101345 0.854629 0.040 Uiso 1 1 calc R U . . .
O2 O 0.2536(2) 0.8537(12) 0.6856(4) 0.0387(15) Uani 1 1 d . . . . .


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 1.244(7) . ?
N1 C2 1.368(8) . ?
N1 N1 1.369(10) 2_656 ?
N1 N2 1.436(8) . ?
C1 N3 1.377(8) . ?
C1 C2 1.378(9) . ?
C1 C3 1.447(9) . ?
C2 N4 1.326(8) . ?
N4 H4A 0.8800 . ?
N4 H4B 0.8800 . ?
N3 O2 1.256(8) . ?
N2 C3 1.318(8) . ?
C3 N5 1.326(8) . ?
N5 H5A 0.8800 . ?
N5 H5B 0.8800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 N1 N1 118.2(6) . 2_656 ?
C2 N1 N2 111.5(5) . . ?
N1 N1 N2 117.9(4) 2_656 . ?
N3 C1 C2 125.4(6) . . ?
N3 C1 C3 127.1(6) . . ?
C2 C1 C3 107.4(5) . . ?
N4 C2 N1 122.0(6) . . ?
N4 C2 C1 132.5(6) . . ?
N1 C2 C1 105.5(5) . . ?
C2 N4 H4A 120.0 . . ?
C2 N4 H4B 120.0 . . ?
H4A N4 H4B 120.0 . . ?
O1 N3 O2 122.7(5) . . ?
O1 N3 C1 118.1(6) . . ?
O2 N3 C1 119.2(5) . . ?
C3 N2 N1 104.6(5) . . ?
N2 C3 N5 122.4(6) . . ?
N2 C3 C1 110.3(6) . . ?
N5 C3 C1 127.3(6) . . ?
C3 N5 H5A 120.0 . . ?
C3 N5 H5B 120.0 . . ?
H5A N5 H5B 120.0 . . ?

####################################################################### 
# 
# 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_2_0m
_database_code_depnum_ccdc_archive 'CCDC 2097304'
loop_
_audit_author_name
_audit_author_address
'Yongxing Tang'
;Nanjing University of Science and Technology
China
;
_audit_update_record             
;
2021-07-19 deposited with the CCDC.	2021-09-13 downloaded from the CCDC.
;
_audit_creation_date             2021-07-13
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H27 N5 O3'
_chemical_formula_sum            'C18 H27 N5 O3'
_chemical_formula_weight         361.44
_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                   9.1659(10)
_cell_length_b                   22.9892(18)
_cell_length_c                   9.3626(8)
_cell_angle_alpha                90
_cell_angle_beta                 102.482(3)
_cell_angle_gamma                90
_cell_volume                     1926.2(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1414
_cell_measurement_temperature    188(2)
_cell_measurement_theta_max      25.85
_cell_measurement_theta_min      2.40
_shelx_estimated_absorpt_T_max   0.992
_shelx_estimated_absorpt_T_min   0.990
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6225
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.246
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             776
_exptl_crystal_size_max          0.12
_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  0.0911
_diffrn_reflns_av_unetI/netI     0.0870
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            14444
_diffrn_reflns_point_group_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.451
_diffrn_reflns_theta_min         2.398
_diffrn_ambient_temperature      188.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.974
_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                2472
_reflns_number_total             3875
_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 (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.227
_refine_diff_density_min         -0.229
_refine_diff_density_rms         0.052
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     250
_refine_ls_number_reflns         3875
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1096
_refine_ls_R_factor_gt           0.0574
_refine_ls_restrained_S_all      1.049
_refine_ls_shift/su_max          0.007
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0492P)²+0.4927P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1147
_refine_ls_wR_factor_ref         0.1407
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C5(H5), C9(H9)
2.b X=CH2 refined with riding coordinates:
 N2(H2A,H2B)
2.c Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C12(H12A,H12B,H12C), C13(H13A,H13B,H13C), C15(H15A,H15B,
 H15C), C16(H16A,H16B,H16C), C17(H17A,H17B,H17C), C18(H18A,H18B,H18C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.61762(19) 0.61335(7) 0.70075(17) 0.0288(4) Uani 1 1 d . . . . .
O2 O -0.09222(19) 0.74778(6) 0.09189(19) 0.0316(4) Uani 1 1 d . . . . .
O3 O -0.2155(2) 0.68775(7) -0.07042(19) 0.0375(5) Uani 1 1 d . . . . .
N1 N -0.1153(2) 0.69736(8) 0.0396(2) 0.0251(5) Uani 1 1 d . . . . .
N2 N 0.1419(2) 0.70128(8) 0.3126(2) 0.0323(5) Uani 1 1 d . . . . .
H2A H 0.2171 0.6970 0.3882 0.039 Uiso 1 1 calc R . . . .
H2B H 0.1000 0.7356 0.2930 0.039 Uiso 1 1 calc R . . . .
N3 N 0.1471(2) 0.60149(8) 0.2471(2) 0.0219(5) Uani 1 1 d . . . . .
N4 N 0.0680(2) 0.56130(8) 0.1446(2) 0.0228(5) Uani 1 1 d . . . . .
N5 N -0.1402(3) 0.56819(10) -0.0491(2) 0.0304(6) Uani 1 1 d . . . . .
C1 C -0.0382(3) 0.59243(9) 0.0608(2) 0.0203(5) Uani 1 1 d . . . . .
C2 C -0.0285(3) 0.65202(9) 0.1057(2) 0.0212(5) Uani 1 1 d . . . . .
C3 C 0.0914(3) 0.65549(9) 0.2271(2) 0.0219(5) Uani 1 1 d . . . . .
C4 C 0.2787(3) 0.58242(9) 0.3573(2) 0.0220(5) Uani 1 1 d . . . . .
C5 C 0.2500(3) 0.58932(10) 0.5079(2) 0.0240(5) Uani 1 1 d . . . . .
H5 H 0.1517 0.5825 0.5215 0.029 Uiso 1 1 calc R . . . .
C6 C 0.3553(3) 0.60463(9) 0.6244(2) 0.0228(5) Uani 1 1 d . . . . .
C7 C 0.5081(3) 0.61676(9) 0.6000(2) 0.0202(5) Uani 1 1 d . . . . .
C8 C 0.5249(3) 0.63109(9) 0.4482(2) 0.0221(5) Uani 1 1 d . . . . .
C9 C 0.4143(3) 0.61517(10) 0.3383(2) 0.0237(5) Uani 1 1 d . . . . .
H9 H 0.4219 0.6252 0.2418 0.028 Uiso 1 1 calc R . . . .
C10 C 0.6713(3) 0.65739(11) 0.4232(3) 0.0285(6) Uani 1 1 d . . . . .
C11 C 0.7286(3) 0.70734(12) 0.5288(3) 0.0393(7) Uani 1 1 d . . . . .
H11A H 0.8229 0.7220 0.5096 0.059 Uiso 1 1 calc GR . . . .
H11B H 0.7451 0.6932 0.6297 0.059 Uiso 1 1 calc GR . . . .
H11C H 0.6546 0.7387 0.5145 0.059 Uiso 1 1 calc GR . . . .
C12 C 0.7912(3) 0.60972(12) 0.4435(3) 0.0438(7) Uani 1 1 d . . . . .
H12A H 0.8826 0.6254 0.4200 0.066 Uiso 1 1 calc GR . . . .
H12B H 0.7550 0.5770 0.3783 0.066 Uiso 1 1 calc GR . . . .
H12C H 0.8127 0.5963 0.5453 0.066 Uiso 1 1 calc GR . . . .
C13 C 0.6503(3) 0.68127(13) 0.2672(3) 0.0442(8) Uani 1 1 d . . . . .
H13A H 0.7406 0.7023 0.2571 0.066 Uiso 1 1 calc GR . . . .
H13B H 0.5647 0.7078 0.2474 0.066 Uiso 1 1 calc GR . . . .
H13C H 0.6323 0.6490 0.1973 0.066 Uiso 1 1 calc GR . . . .
C14 C 0.3265(3) 0.60536(11) 0.7801(3) 0.0320(6) Uani 1 1 d . . . . .
C15 C 0.1598(4) 0.60214(19) 0.7762(3) 0.0726(12) Uani 1 1 d . . . . .
H15A H 0.1432 0.6063 0.8757 0.109 Uiso 1 1 calc GR . . . .
H15B H 0.1207 0.5645 0.7358 0.109 Uiso 1 1 calc GR . . . .
H15C H 0.1081 0.6335 0.7146 0.109 Uiso 1 1 calc GR . . . .
C16 C 0.4021(4) 0.55225(12) 0.8657(3) 0.0473(8) Uani 1 1 d . . . . .
H16A H 0.3769 0.5510 0.9622 0.071 Uiso 1 1 calc GR . . . .
H16B H 0.5108 0.5554 0.8777 0.071 Uiso 1 1 calc GR . . . .
H16C H 0.3669 0.5166 0.8117 0.071 Uiso 1 1 calc GR . . . .
C17 C 0.3897(3) 0.66077(11) 0.8606(3) 0.0407(7) Uani 1 1 d . . . . .
H17A H 0.3612 0.6625 0.9555 0.061 Uiso 1 1 calc GR . . . .
H17B H 0.3496 0.6948 0.8020 0.061 Uiso 1 1 calc GR . . . .
H17C H 0.4989 0.6605 0.8757 0.061 Uiso 1 1 calc GR . . . .
C18 C 0.3060(3) 0.51748(10) 0.3318(3) 0.0366(7) Uani 1 1 d . . . . .
H18A H 0.3924 0.5039 0.4052 0.055 Uiso 1 1 calc GR . . . .
H18B H 0.3256 0.5122 0.2338 0.055 Uiso 1 1 calc GR . . . .
H18C H 0.2174 0.4950 0.3403 0.055 Uiso 1 1 calc GR . . . .
H5A H -0.120(3) 0.5325(13) -0.075(3) 0.041(8) Uiso 1 1 d . . . . .
H5B H -0.194(3) 0.5912(11) -0.107(3) 0.035(8) Uiso 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 C7 1.223(3) . ?
O2 N1 1.258(2) . ?
O3 N1 1.243(2) . ?
N1 C2 1.375(3) . ?
N2 H2A 0.8800 . ?
N2 H2B 0.8800 . ?
N2 C3 1.342(3) . ?
N3 N4 1.414(2) . ?
N3 C3 1.340(3) . ?
N3 C4 1.475(3) . ?
N4 C1 1.321(3) . ?
N5 C1 1.352(3) . ?
N5 H5A 0.89(3) . ?
N5 H5B 0.84(3) . ?
C1 C2 1.430(3) . ?
C2 C3 1.402(3) . ?
C4 C5 1.497(3) . ?
C4 C9 1.496(3) . ?
C4 C18 1.541(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.338(3) . ?
C6 C7 1.493(3) . ?
C6 C14 1.536(3) . ?
C7 C8 1.499(3) . ?
C8 C9 1.330(3) . ?
C8 C10 1.535(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.532(3) . ?
C10 C12 1.535(4) . ?
C10 C13 1.533(3) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 C15 1.523(4) . ?
C14 C16 1.541(4) . ?
C14 C17 1.529(4) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 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
O2 N1 C2 119.43(19) . . ?
O3 N1 O2 121.21(19) . . ?
O3 N1 C2 119.36(19) . . ?
H2A N2 H2B 120.0 . . ?
C3 N2 H2A 120.0 . . ?
C3 N2 H2B 120.0 . . ?
N4 N3 C4 120.18(17) . . ?
C3 N3 N4 112.74(17) . . ?
C3 N3 C4 127.05(18) . . ?
C1 N4 N3 104.67(17) . . ?
C1 N5 H5A 116.1(18) . . ?
C1 N5 H5B 116.4(18) . . ?
H5A N5 H5B 122(2) . . ?
N4 C1 N5 121.9(2) . . ?
N4 C1 C2 110.67(19) . . ?
N5 C1 C2 127.4(2) . . ?
N1 C2 C1 126.9(2) . . ?
N1 C2 C3 126.7(2) . . ?
C3 C2 C1 106.33(19) . . ?
N2 C3 C2 129.6(2) . . ?
N3 C3 N2 124.8(2) . . ?
N3 C3 C2 105.58(19) . . ?
N3 C4 C5 110.10(19) . . ?
N3 C4 C9 110.02(18) . . ?
N3 C4 C18 108.38(18) . . ?
C5 C4 C18 108.42(19) . . ?
C9 C4 C5 112.22(19) . . ?
C9 C4 C18 107.6(2) . . ?
C4 C5 H5 118.2 . . ?
C6 C5 C4 123.6(2) . . ?
C6 C5 H5 118.2 . . ?
C5 C6 C7 117.3(2) . . ?
C5 C6 C14 122.3(2) . . ?
C7 C6 C14 120.2(2) . . ?
O1 C7 C6 120.7(2) . . ?
O1 C7 C8 120.7(2) . . ?
C6 C7 C8 118.60(19) . . ?
C7 C8 C10 120.3(2) . . ?
C9 C8 C7 117.1(2) . . ?
C9 C8 C10 122.4(2) . . ?
C4 C9 H9 118.0 . . ?
C8 C9 C4 124.1(2) . . ?
C8 C9 H9 118.0 . . ?
C8 C10 C13 110.7(2) . . ?
C11 C10 C8 112.7(2) . . ?
C11 C10 C12 108.6(2) . . ?
C11 C10 C13 107.5(2) . . ?
C12 C10 C8 109.0(2) . . ?
C12 C10 C13 108.2(2) . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C10 C12 H12A 109.5 . . ?
C10 C12 H12B 109.5 . . ?
C10 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C10 C13 H13A 109.5 . . ?
C10 C13 H13B 109.5 . . ?
C10 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C6 C14 C16 109.6(2) . . ?
C15 C14 C6 110.7(2) . . ?
C15 C14 C16 108.1(3) . . ?
C15 C14 C17 108.9(3) . . ?
C17 C14 C6 110.6(2) . . ?
C17 C14 C16 108.9(2) . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C14 C16 H16A 109.5 . . ?
C14 C16 H16B 109.5 . . ?
C14 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C14 C17 H17A 109.5 . . ?
C14 C17 H17B 109.5 . . ?
C14 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C4 C18 H18A 109.5 . . ?
C4 C18 H18B 109.5 . . ?
C4 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H2A O2 0.88 2.62 3.375(3) 144.5 4_676
N2 H2B O2 0.88 2.30 2.846(3) 120.2 .
N5 H5B O1 0.84(3) 2.27(3) 3.040(3) 154(2) 1_454
N5 H5B O3 0.84(3) 2.26(3) 2.830(3) 125(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 C7 C8 C9 157.7(2) . . . . ?
O1 C7 C8 C10 -16.4(3) . . . . ?
O2 N1 C2 C1 -179.4(2) . . . . ?
O2 N1 C2 C3 -2.3(4) . . . . ?
O3 N1 C2 C1 0.8(4) . . . . ?
O3 N1 C2 C3 177.9(2) . . . . ?
N1 C2 C3 N2 5.6(4) . . . . ?
N1 C2 C3 N3 -176.5(2) . . . . ?
N3 N4 C1 N5 -178.3(2) . . . . ?
N3 N4 C1 C2 0.7(2) . . . . ?
N3 C4 C5 C6 -144.8(2) . . . . ?
N3 C4 C9 C8 145.2(2) . . . . ?
N4 N3 C3 N2 177.3(2) . . . . ?
N4 N3 C3 C2 -0.7(3) . . . . ?
N4 N3 C4 C5 -116.9(2) . . . . ?
N4 N3 C4 C9 118.9(2) . . . . ?
N4 N3 C4 C18 1.6(3) . . . . ?
N4 C1 C2 N1 176.4(2) . . . . ?
N4 C1 C2 C3 -1.2(3) . . . . ?
N5 C1 C2 N1 -4.7(4) . . . . ?
N5 C1 C2 C3 177.7(2) . . . . ?
C1 C2 C3 N2 -176.8(2) . . . . ?
C1 C2 C3 N3 1.1(3) . . . . ?
C3 N3 N4 C1 0.0(2) . . . . ?
C3 N3 C4 C5 65.3(3) . . . . ?
C3 N3 C4 C9 -58.9(3) . . . . ?
C3 N3 C4 C18 -176.2(2) . . . . ?
C4 N3 N4 C1 -178.1(2) . . . . ?
C4 N3 C3 N2 -4.7(4) . . . . ?
C4 N3 C3 C2 177.2(2) . . . . ?
C4 C5 C6 C7 1.6(3) . . . . ?
C4 C5 C6 C14 -173.7(2) . . . . ?
C5 C4 C9 C8 22.3(3) . . . . ?
C5 C6 C7 O1 -157.4(2) . . . . ?
C5 C6 C7 C8 20.4(3) . . . . ?
C5 C6 C14 C15 -14.5(4) . . . . ?
C5 C6 C14 C16 104.6(3) . . . . ?
C5 C6 C14 C17 -135.3(2) . . . . ?
C6 C7 C8 C9 -20.1(3) . . . . ?
C6 C7 C8 C10 165.8(2) . . . . ?
C7 C6 C14 C15 170.4(3) . . . . ?
C7 C6 C14 C16 -70.5(3) . . . . ?
C7 C6 C14 C17 49.6(3) . . . . ?
C7 C8 C9 C4 -2.2(3) . . . . ?
C7 C8 C10 C11 -46.3(3) . . . . ?
C7 C8 C10 C12 74.3(3) . . . . ?
C7 C8 C10 C13 -166.8(2) . . . . ?
C9 C4 C5 C6 -21.9(3) . . . . ?
C9 C8 C10 C11 140.0(2) . . . . ?
C9 C8 C10 C12 -99.4(3) . . . . ?
C9 C8 C10 C13 19.5(3) . . . . ?
C10 C8 C9 C4 171.7(2) . . . . ?
C14 C6 C7 O1 18.0(3) . . . . ?
C14 C6 C7 C8 -164.2(2) . . . . ?
C18 C4 C5 C6 96.8(3) . . . . ?
C18 C4 C9 C8 -96.9(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
