# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2022

####################################################################### 
# 
# 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_220515_wq_nlg_yb_3_0m
_audit_block_doi                 10.5517/ccdc.csd.cc2cbfy3
_database_code_depnum_ccdc_archive 'CCDC 2184785'
loop_
_audit_author_name
_audit_author_address
'Haoran Hu'
;Nanjing University of Science and Technology
China
;
_audit_update_record             
;
2022-07-08 deposited with the CCDC.	2022-09-05 downloaded from the CCDC.
;
_audit_creation_date             2022-05-16
_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        ?
_chemical_formula_moiety         'C14 H15 N5'
_chemical_formula_sum            'C14 H15 N5'
_chemical_formula_weight         253.31
_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'

_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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.7299(5)
_cell_length_b                   9.2355(5)
_cell_length_c                   9.5254(5)
_cell_angle_alpha                65.084(2)
_cell_angle_beta                 68.436(2)
_cell_angle_gamma                73.691(2)
_cell_volume                     640.49(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    8993
_cell_measurement_temperature    193.00
_cell_measurement_theta_max      27.488
_cell_measurement_theta_min      2.537
_shelx_estimated_absorpt_T_max   0.989
_shelx_estimated_absorpt_T_min   0.987
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.7167
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0761 before and 0.0510 after correction.
The Ratio of minimum to maximum transmission is 0.9612.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.313
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             268
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.13
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0380
_diffrn_reflns_av_unetI/netI     0.0229
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            20760
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.488
_diffrn_reflns_theta_min         2.459
_diffrn_ambient_temperature      193.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.41
_diffrn_source_power             0.0705
_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                2629
_reflns_number_total             2926
_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         0.263
_refine_diff_density_min         -0.211
_refine_diff_density_rms         0.039
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.100
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     174
_refine_ls_number_reflns         2926
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0436
_refine_ls_R_factor_gt           0.0401
_refine_ls_restrained_S_all      1.100
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0556P)²+0.1364P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1099
_refine_ls_wR_factor_ref         0.1127
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C4(H4), C6(H6), C11(H11), C12(H12), C13(H13), C14(H14)
2.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C8(H8A,H8B,H8C)
;
_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
N1 N 0.84380(12) 1.19141(11) 0.07154(12) 0.0299(2) Uani 1 1 d . . . . .
N2 N 0.73830(13) 1.22535(12) -0.01638(13) 0.0374(3) Uani 1 1 d . . . . .
N3 N 0.74135(11) 0.79857(10) 0.22660(11) 0.0280(2) Uani 1 1 d . . . . .
N4 N 0.64007(11) 0.75551(10) 0.18861(11) 0.0273(2) Uani 1 1 d . . . . .
N5 N 0.52045(11) 0.37050(11) 0.32902(11) 0.0278(2) Uani 1 1 d . . . . .
C1 C 0.92796(16) 1.31809(15) 0.04914(16) 0.0369(3) Uani 1 1 d . . . . .
H1A H 1.001819 1.353303 -0.061405 0.055 Uiso 1 1 calc R U . . .
H1B H 0.993731 1.276620 0.125916 0.055 Uiso 1 1 calc R U . . .
H1C H 0.845089 1.409792 0.067792 0.055 Uiso 1 1 calc R U . . .
C2 C 0.85790(14) 1.03621(13) 0.16881(14) 0.0307(2) Uani 1 1 d . . . . .
H2 H 0.925165 0.986075 0.240603 0.037 Uiso 1 1 calc R U . . .
C3 C 0.75648(13) 0.96260(12) 0.14535(13) 0.0268(2) Uani 1 1 d . . . . .
C4 C 0.68525(15) 1.08677(13) 0.02806(15) 0.0347(3) Uani 1 1 d . . . . .
H4 H 0.609055 1.073213 -0.013916 0.042 Uiso 1 1 calc R U . . .
C5 C 0.62530(13) 0.59321(12) 0.26475(12) 0.0264(2) Uani 1 1 d . . . . .
C6 C 0.51228(13) 0.53155(12) 0.24304(12) 0.0280(2) Uani 1 1 d . . . . .
H6 H 0.439572 0.592680 0.177658 0.034 Uiso 1 1 calc R U . . .
C7 C 0.41883(15) 0.25966(14) 0.34465(14) 0.0331(3) Uani 1 1 d . . . . .
H7A H 0.347414 0.221580 0.457519 0.040 Uiso 1 1 calc R U . . .
H7B H 0.493249 0.164326 0.321920 0.040 Uiso 1 1 calc R U . . .
C8 C 0.30992(17) 0.33483(17) 0.23283(17) 0.0430(3) Uani 1 1 d . . . . .
H8A H 0.379576 0.373571 0.120778 0.064 Uiso 1 1 calc R U . . .
H8B H 0.231512 0.425711 0.258562 0.064 Uiso 1 1 calc R U . . .
H8C H 0.247837 0.254089 0.246447 0.064 Uiso 1 1 calc R U . . .
C9 C 0.63972(13) 0.32416(13) 0.40964(12) 0.0270(2) Uani 1 1 d . . . . .
C10 C 0.70961(13) 0.46075(12) 0.37290(12) 0.0261(2) Uani 1 1 d . . . . .
C11 C 0.83502(15) 0.44146(14) 0.44045(14) 0.0329(3) Uani 1 1 d . . . . .
H11 H 0.884866 0.531183 0.417282 0.039 Uiso 1 1 calc R U . . .
C12 C 0.88541(16) 0.28935(15) 0.54174(17) 0.0417(3) Uani 1 1 d . . . . .
H12 H 0.970087 0.275354 0.588584 0.050 Uiso 1 1 calc R U . . .
C13 C 0.81353(17) 0.15584(14) 0.57621(17) 0.0416(3) Uani 1 1 d . . . . .
H13 H 0.850434 0.052939 0.646071 0.050 Uiso 1 1 calc R U . . .
C14 C 0.69043(15) 0.17083(13) 0.51083(14) 0.0335(3) Uani 1 1 d . . . . .
H14 H 0.642038 0.080244 0.533801 0.040 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
N1 N2 1.3534(13) . ?
N1 C1 1.4531(14) . ?
N1 C2 1.3393(14) . ?
N2 C4 1.3282(15) . ?
N3 N4 1.2746(13) . ?
N3 C3 1.4003(13) . ?
N4 C5 1.3832(13) . ?
N5 C6 1.3584(13) . ?
N5 C7 1.4634(14) . ?
N5 C9 1.3848(14) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 H2 0.9500 . ?
C2 C3 1.3812(15) . ?
C3 C4 1.4073(15) . ?
C4 H4 0.9500 . ?
C5 C6 1.3803(15) . ?
C5 C10 1.4454(14) . ?
C6 H6 0.9500 . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C8 1.5070(17) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 C10 1.4105(15) . ?
C9 C14 1.3935(15) . ?
C10 C11 1.3986(15) . ?
C11 H11 0.9500 . ?
C11 C12 1.3859(16) . ?
C12 H12 0.9500 . ?
C12 C13 1.4014(18) . ?
C13 H13 0.9500 . ?
C13 C14 1.3776(17) . ?
C14 H14 0.9500 . ?

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 119.35(10) . . ?
C2 N1 N2 112.05(9) . . ?
C2 N1 C1 128.57(10) . . ?
C4 N2 N1 105.08(9) . . ?
N4 N3 C3 113.00(9) . . ?
N3 N4 C5 114.20(9) . . ?
C6 N5 C7 127.92(9) . . ?
C6 N5 C9 108.63(9) . . ?
C9 N5 C7 123.40(9) . . ?
N1 C1 H1A 109.5 . . ?
N1 C1 H1B 109.5 . . ?
N1 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
N1 C2 H2 126.4 . . ?
N1 C2 C3 107.27(9) . . ?
C3 C2 H2 126.4 . . ?
N3 C3 C4 132.58(10) . . ?
C2 C3 N3 123.08(10) . . ?
C2 C3 C4 104.33(9) . . ?
N2 C4 C3 111.27(10) . . ?
N2 C4 H4 124.4 . . ?
C3 C4 H4 124.4 . . ?
N4 C5 C10 132.22(10) . . ?
C6 C5 N4 120.54(9) . . ?
C6 C5 C10 107.25(9) . . ?
N5 C6 C5 109.91(9) . . ?
N5 C6 H6 125.0 . . ?
C5 C6 H6 125.0 . . ?
N5 C7 H7A 108.9 . . ?
N5 C7 H7B 108.9 . . ?
N5 C7 C8 113.31(10) . . ?
H7A C7 H7B 107.7 . . ?
C8 C7 H7A 108.9 . . ?
C8 C7 H7B 108.9 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N5 C9 C10 108.87(9) . . ?
N5 C9 C14 128.52(10) . . ?
C14 C9 C10 122.61(10) . . ?
C9 C10 C5 105.34(9) . . ?
C11 C10 C5 135.97(10) . . ?
C11 C10 C9 118.69(10) . . ?
C10 C11 H11 120.5 . . ?
C12 C11 C10 118.94(10) . . ?
C12 C11 H11 120.5 . . ?
C11 C12 H12 119.4 . . ?
C11 C12 C13 121.10(11) . . ?
C13 C12 H12 119.4 . . ?
C12 C13 H13 119.3 . . ?
C14 C13 C12 121.32(11) . . ?
C14 C13 H13 119.3 . . ?
C9 C14 H14 121.3 . . ?
C13 C14 C9 117.34(10) . . ?
C13 C14 H14 121.3 . . ?

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
N1 N2 C4 C3 0.07(14) . . . . ?
N1 C2 C3 N3 179.34(9) . . . . ?
N1 C2 C3 C4 0.22(13) . . . . ?
N2 N1 C2 C3 -0.20(13) . . . . ?
N3 N4 C5 C6 175.89(9) . . . . ?
N3 N4 C5 C10 -3.90(17) . . . . ?
N3 C3 C4 N2 -179.18(11) . . . . ?
N4 N3 C3 C2 179.31(10) . . . . ?
N4 N3 C3 C4 -1.85(17) . . . . ?
N4 C5 C6 N5 179.90(9) . . . . ?
N4 C5 C10 C9 179.97(11) . . . . ?
N4 C5 C10 C11 -0.9(2) . . . . ?
N5 C9 C10 C5 -0.01(11) . . . . ?
N5 C9 C10 C11 -179.33(9) . . . . ?
N5 C9 C14 C13 179.57(11) . . . . ?
C1 N1 N2 C4 178.64(10) . . . . ?
C1 N1 C2 C3 -178.59(11) . . . . ?
C2 N1 N2 C4 0.08(14) . . . . ?
C2 C3 C4 N2 -0.19(14) . . . . ?
C3 N3 N4 C5 178.76(8) . . . . ?
C5 C10 C11 C12 -179.46(12) . . . . ?
C6 N5 C7 C8 8.50(17) . . . . ?
C6 N5 C9 C10 -0.15(12) . . . . ?
C6 N5 C9 C14 -179.58(11) . . . . ?
C6 C5 C10 C9 0.17(11) . . . . ?
C6 C5 C10 C11 179.31(12) . . . . ?
C7 N5 C6 C5 177.68(10) . . . . ?
C7 N5 C9 C10 -177.71(9) . . . . ?
C7 N5 C9 C14 2.87(18) . . . . ?
C9 N5 C6 C5 0.26(12) . . . . ?
C9 N5 C7 C8 -174.43(10) . . . . ?
C9 C10 C11 C12 -0.41(17) . . . . ?
C10 C5 C6 N5 -0.27(12) . . . . ?
C10 C9 C14 C13 0.21(17) . . . . ?
C10 C11 C12 C13 0.3(2) . . . . ?
C11 C12 C13 C14 0.0(2) . . . . ?
C12 C13 C14 C9 -0.3(2) . . . . ?
C14 C9 C10 C5 179.45(10) . . . . ?
C14 C9 C10 C11 0.14(16) . . . . ?

_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_220515_wq_nlg_yb_4_0m
_database_code_depnum_ccdc_archive 'CCDC 2184786'
loop_
_audit_author_name
_audit_author_address
'Hu Haoran'
;nanjing university of science and technology
China
;
_audit_update_record             
;
2022-07-08 deposited with the CCDC.	2022-09-05 downloaded from the CCDC.
;
_audit_creation_date             2022-05-16
_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        ?
_chemical_formula_moiety         'C15 H17 N5'
_chemical_formula_sum            'C15 H17 N5'
_chemical_formula_weight         267.33
_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'

_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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.2845(5)
_cell_length_b                   9.2942(5)
_cell_length_c                   9.4489(4)
_cell_angle_alpha                67.465(2)
_cell_angle_beta                 69.500(2)
_cell_angle_gamma                70.108(2)
_cell_volume                     685.12(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9279
_cell_measurement_temperature    193.00
_cell_measurement_theta_max      27.486
_cell_measurement_theta_min      2.443
_shelx_estimated_absorpt_T_max   0.988
_shelx_estimated_absorpt_T_min   0.984
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_T_max  0.4305
_exptl_absorpt_correction_T_min  0.4066
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0941 before and 0.0535 after correction.
The Ratio of minimum to maximum transmission is 0.9445.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.296
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             284
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.15
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0419
_diffrn_reflns_av_unetI/netI     0.0279
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            22511
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.486
_diffrn_reflns_theta_min         2.411
_diffrn_ambient_temperature      193.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_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                2820
_reflns_number_total             3127
_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         0.256
_refine_diff_density_min         -0.219
_refine_diff_density_rms         0.041
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     183
_refine_ls_number_reflns         3127
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0438
_refine_ls_R_factor_gt           0.0404
_refine_ls_restrained_S_all      1.059
_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)+(0.0582P)²+0.1354P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1083
_refine_ls_wR_factor_ref         0.1112
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C2(H2A,H2B)
2.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C8(H8), C9(H9), C10(H10), C11(H11), C13(H13), C14(H14)
2.c Idealised Me refined as rotating group:
 C3(H3A,H3B,H3C), C15(H15A,H15B,H15C)
;
_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
N1 N 0.46043(10) 0.61165(10) 0.67437(10) 0.0284(2) Uani 1 1 d . . . . .
N2 N 0.35562(10) 0.23957(10) 0.80883(10) 0.0292(2) Uani 1 1 d . . . . .
N3 N 0.25602(10) 0.20062(10) 0.77443(10) 0.0301(2) Uani 1 1 d . . . . .
N4 N 0.16904(11) -0.18127(11) 0.93310(11) 0.0309(2) Uani 1 1 d . . . . .
N5 N 0.26737(12) -0.21132(11) 1.02350(12) 0.0363(2) Uani 1 1 d . . . . .
C1 C 0.55418(13) 0.71582(13) 0.66340(13) 0.0309(2) Uani 1 1 d . . . . .
H1A H 0.481967 0.817800 0.679951 0.037 Uiso 1 1 calc R U . . .
H1B H 0.624937 0.741268 0.555399 0.037 Uiso 1 1 calc R U . . .
C2 C 0.65318(14) 0.64169(14) 0.78255(14) 0.0368(3) Uani 1 1 d . . . . .
H2A H 0.734279 0.546449 0.758983 0.044 Uiso 1 1 calc R U . . .
H2B H 0.584757 0.606046 0.890182 0.044 Uiso 1 1 calc R U . . .
C3 C 0.73382(16) 0.76173(17) 0.77730(17) 0.0466(3) Uani 1 1 d . . . . .
H3A H 0.803780 0.794722 0.671554 0.070 Uiso 1 1 calc R U . . .
H3B H 0.796225 0.712030 0.856138 0.070 Uiso 1 1 calc R U . . .
H3C H 0.653477 0.855889 0.800825 0.070 Uiso 1 1 calc R U . . .
C4 C 0.47354(12) 0.45369(12) 0.75682(12) 0.0295(2) Uani 1 1 d . . . . .
H4 H 0.545920 0.391182 0.820641 0.035 Uiso 1 1 calc R U . . .
C5 C 0.36610(12) 0.39749(12) 0.73410(12) 0.0281(2) Uani 1 1 d . . . . .
C6 C 0.28097(12) 0.52955(12) 0.62788(12) 0.0278(2) Uani 1 1 d . . . . .
C7 C 0.34432(12) 0.66115(12) 0.59363(12) 0.0279(2) Uani 1 1 d . . . . .
C8 C 0.29263(13) 0.81210(13) 0.49363(13) 0.0333(2) Uani 1 1 d . . . . .
H8 H 0.336194 0.899184 0.472837 0.040 Uiso 1 1 calc R U . . .
C9 C 0.17517(15) 0.83011(14) 0.42574(15) 0.0393(3) Uani 1 1 d . . . . .
H9 H 0.137552 0.931461 0.356320 0.047 Uiso 1 1 calc R U . . .
C10 C 0.11075(14) 0.70176(14) 0.45745(15) 0.0397(3) Uani 1 1 d . . . . .
H10 H 0.030628 0.717591 0.408564 0.048 Uiso 1 1 calc R U . . .
C11 C 0.16122(13) 0.55202(13) 0.55858(14) 0.0340(2) Uani 1 1 d . . . . .
H11 H 0.115357 0.466267 0.580419 0.041 Uiso 1 1 calc R U . . .
C12 C 0.24447(12) 0.04176(12) 0.85722(12) 0.0282(2) Uani 1 1 d . . . . .
C13 C 0.31335(13) -0.07617(13) 0.97780(13) 0.0335(2) Uani 1 1 d . . . . .
H13 H 0.383583 -0.061057 1.020863 0.040 Uiso 1 1 calc R U . . .
C14 C 0.15206(13) -0.03150(13) 0.83322(13) 0.0326(2) Uani 1 1 d . . . . .
H14 H 0.088339 0.015315 0.759730 0.039 Uiso 1 1 calc R U . . .
C15 C 0.09433(14) -0.30513(14) 0.95498(15) 0.0385(3) Uani 1 1 d . . . . .
H15A H 0.175755 -0.403172 0.944268 0.058 Uiso 1 1 calc R U . . .
H15B H 0.035139 -0.268572 0.874687 0.058 Uiso 1 1 calc R U . . .
H15C H 0.021701 -0.327211 1.060729 0.058 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
N1 C1 1.4626(13) . ?
N1 C4 1.3584(13) . ?
N1 C7 1.3876(13) . ?
N2 N3 1.2730(13) . ?
N2 C5 1.3846(13) . ?
N3 C12 1.4026(13) . ?
N4 N5 1.3531(13) . ?
N4 C14 1.3421(14) . ?
N4 C15 1.4524(14) . ?
N5 C13 1.3292(14) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C1 C2 1.5121(15) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C3 1.5192(16) . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C4 H4 0.9500 . ?
C4 C5 1.3799(15) . ?
C5 C6 1.4457(14) . ?
C6 C7 1.4140(14) . ?
C6 C11 1.3984(15) . ?
C7 C8 1.3910(14) . ?
C8 H8 0.9500 . ?
C8 C9 1.3829(16) . ?
C9 H9 0.9500 . ?
C9 C10 1.3988(17) . ?
C10 H10 0.9500 . ?
C10 C11 1.3856(16) . ?
C11 H11 0.9500 . ?
C12 C13 1.4087(14) . ?
C12 C14 1.3796(15) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 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
C4 N1 C1 127.54(9) . . ?
C4 N1 C7 108.67(8) . . ?
C7 N1 C1 123.75(8) . . ?
N3 N2 C5 114.57(9) . . ?
N2 N3 C12 112.78(9) . . ?
N5 N4 C15 119.48(9) . . ?
C14 N4 N5 112.11(9) . . ?
C14 N4 C15 128.39(10) . . ?
C13 N5 N4 105.04(9) . . ?
N1 C1 H1A 108.9 . . ?
N1 C1 H1B 108.9 . . ?
N1 C1 C2 113.17(9) . . ?
H1A C1 H1B 107.8 . . ?
C2 C1 H1A 108.9 . . ?
C2 C1 H1B 108.9 . . ?
C1 C2 H2A 109.5 . . ?
C1 C2 H2B 109.5 . . ?
C1 C2 C3 110.67(10) . . ?
H2A C2 H2B 108.1 . . ?
C3 C2 H2A 109.5 . . ?
C3 C2 H2B 109.5 . . ?
C2 C3 H3A 109.5 . . ?
C2 C3 H3B 109.5 . . ?
C2 C3 H3C 109.5 . . ?
H3A C3 H3B 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
N1 C4 H4 125.0 . . ?
N1 C4 C5 109.91(9) . . ?
C5 C4 H4 125.0 . . ?
N2 C5 C6 132.17(10) . . ?
C4 C5 N2 120.43(9) . . ?
C4 C5 C6 107.40(9) . . ?
C7 C6 C5 105.26(9) . . ?
C11 C6 C5 136.05(10) . . ?
C11 C6 C7 118.69(9) . . ?
N1 C7 C6 108.75(9) . . ?
N1 C7 C8 128.53(10) . . ?
C8 C7 C6 122.73(10) . . ?
C7 C8 H8 121.4 . . ?
C9 C8 C7 117.21(10) . . ?
C9 C8 H8 121.4 . . ?
C8 C9 H9 119.4 . . ?
C8 C9 C10 121.18(10) . . ?
C10 C9 H9 119.4 . . ?
C9 C10 H10 119.3 . . ?
C11 C10 C9 121.46(11) . . ?
C11 C10 H10 119.3 . . ?
C6 C11 H11 120.6 . . ?
C10 C11 C6 118.73(10) . . ?
C10 C11 H11 120.6 . . ?
N3 C12 C13 131.88(10) . . ?
C14 C12 N3 123.69(9) . . ?
C14 C12 C13 104.42(9) . . ?
N5 C13 C12 111.23(10) . . ?
N5 C13 H13 124.4 . . ?
C12 C13 H13 124.4 . . ?
N4 C14 C12 107.18(9) . . ?
N4 C14 H14 126.4 . . ?
C12 C14 H14 126.4 . . ?
N4 C15 H15A 109.5 . . ?
N4 C15 H15B 109.5 . . ?
N4 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 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
N1 C1 C2 C3 -173.94(10) . . . . ?
N1 C4 C5 N2 -178.92(9) . . . . ?
N1 C4 C5 C6 0.81(12) . . . . ?
N1 C7 C8 C9 179.32(10) . . . . ?
N2 N3 C12 C13 5.37(16) . . . . ?
N2 N3 C12 C14 -175.86(9) . . . . ?
N2 C5 C6 C7 179.25(10) . . . . ?
N2 C5 C6 C11 -0.9(2) . . . . ?
N3 N2 C5 C4 -177.74(9) . . . . ?
N3 N2 C5 C6 2.60(16) . . . . ?
N3 C12 C13 N5 179.24(10) . . . . ?
N3 C12 C14 N4 -179.49(9) . . . . ?
N4 N5 C13 C12 -0.03(13) . . . . ?
N5 N4 C14 C12 0.45(13) . . . . ?
C1 N1 C4 C5 -178.59(9) . . . . ?
C1 N1 C7 C6 178.40(9) . . . . ?
C1 N1 C7 C8 -1.46(16) . . . . ?
C4 N1 C1 C2 -12.00(15) . . . . ?
C4 N1 C7 C6 0.57(11) . . . . ?
C4 N1 C7 C8 -179.28(11) . . . . ?
C4 C5 C6 C7 -0.44(11) . . . . ?
C4 C5 C6 C11 179.41(12) . . . . ?
C5 N2 N3 C12 -177.63(8) . . . . ?
C5 C6 C7 N1 -0.07(11) . . . . ?
C5 C6 C7 C8 179.79(9) . . . . ?
C5 C6 C11 C10 -179.00(11) . . . . ?
C6 C7 C8 C9 -0.51(16) . . . . ?
C7 N1 C1 C2 170.60(9) . . . . ?
C7 N1 C4 C5 -0.87(12) . . . . ?
C7 C6 C11 C10 0.83(16) . . . . ?
C7 C8 C9 C10 0.38(18) . . . . ?
C8 C9 C10 C11 0.37(19) . . . . ?
C9 C10 C11 C6 -0.98(18) . . . . ?
C11 C6 C7 N1 -179.96(9) . . . . ?
C11 C6 C7 C8 -0.09(15) . . . . ?
C13 C12 C14 N4 -0.43(12) . . . . ?
C14 N4 N5 C13 -0.26(13) . . . . ?
C14 C12 C13 N5 0.29(13) . . . . ?
C15 N4 N5 C13 -178.94(10) . . . . ?
C15 N4 C14 C12 178.98(10) . . . . ?

_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_20220514_yhj_hnr_yb3_bj_0m
_database_code_depnum_ccdc_archive 'CCDC 2184787'
loop_
_audit_author_name
_audit_author_address
'Hu Haoran'
;nanjing university of science and technology
China
;
_audit_update_record             
;
2022-07-08 deposited with the CCDC.	2022-09-05 downloaded from the CCDC.
;
_audit_creation_date             2022-05-16
_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        ?
_chemical_formula_moiety         'C21 H21 N5'
_chemical_formula_sum            'C21 H21 N5'
_chemical_formula_weight         343.43
_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'

_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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   5.4109(4)
_cell_length_b                   12.3109(6)
_cell_length_c                   14.8982(9)
_cell_angle_alpha                67.826(2)
_cell_angle_beta                 83.410(2)
_cell_angle_gamma                88.031(2)
_cell_volume                     912.90(10)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2081
_cell_measurement_temperature    193.00
_cell_measurement_theta_max      25.564
_cell_measurement_theta_min      2.720
_shelx_estimated_absorpt_T_max   0.991
_shelx_estimated_absorpt_T_min   0.988
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6841
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1077 before and 0.0725 after correction.
The Ratio of minimum to maximum transmission is 0.9175.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.249
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             364
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0703
_diffrn_reflns_av_unetI/netI     0.0510
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            18968
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.451
_diffrn_reflns_theta_min         2.719
_diffrn_ambient_temperature      193.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_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                2623
_reflns_number_total             4149
_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         0.286
_refine_diff_density_min         -0.182
_refine_diff_density_rms         0.040
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     319
_refine_ls_number_reflns         4149
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0903
_refine_ls_R_factor_gt           0.0533
_refine_ls_restrained_S_all      1.033
_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)+(0.0523P)²+0.3041P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1216
_refine_ls_wR_factor_ref         0.1498
_refine_special_details          ?
_olex2_refinement_description    
;
;
_atom_sites_solution_hydrogens   difmap
_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
N1 N 0.9331(3) 0.59301(14) 0.29176(12) 0.0430(4) Uani 1 1 d . . . . .
N2 N 0.6698(3) 0.87574(15) 0.24340(12) 0.0455(4) Uani 1 1 d . . . . .
N3 N 0.5067(3) 0.92480(14) 0.18676(12) 0.0417(4) Uani 1 1 d . . . . .
N4 N 0.3947(3) 1.21077(14) 0.20469(12) 0.0443(4) Uani 1 1 d . . . . .
N5 N 0.2460(3) 1.20448(14) 0.13811(12) 0.0406(4) Uani 1 1 d . . . . .
C1 C 1.1249(5) 0.2860(2) 0.41431(17) 0.0531(6) Uani 1 1 d . . . . .
H1 H 1.287(5) 0.289(2) 0.3717(18) 0.066(7) Uiso 1 1 d . . . . .
C2 C 1.0313(7) 0.1784(2) 0.4798(2) 0.0728(8) Uani 1 1 d . . . . .
H2 H 1.125(6) 0.105(3) 0.488(2) 0.108(11) Uiso 1 1 d . . . . .
C3 C 0.8094(7) 0.1723(3) 0.5359(2) 0.0813(10) Uani 1 1 d . . . . .
H3 H 0.745(6) 0.093(3) 0.582(2) 0.103(10) Uiso 1 1 d . . . . .
C4 C 0.6780(6) 0.2718(3) 0.52627(19) 0.0776(10) Uani 1 1 d . . . . .
H4 H 0.528(5) 0.273(2) 0.560(2) 0.079(9) Uiso 1 1 d . . . . .
C5 C 0.7716(4) 0.3813(3) 0.46158(16) 0.0575(6) Uani 1 1 d . . . . .
H5 H 0.682(4) 0.452(2) 0.4510(16) 0.056(7) Uiso 1 1 d . . . . .
C6 C 0.9981(4) 0.38828(18) 0.40560(14) 0.0418(5) Uani 1 1 d . . . . .
C7 C 1.1123(4) 0.50414(19) 0.33664(17) 0.0466(5) Uani 1 1 d . . . . .
H7A H 1.230(4) 0.490(2) 0.2845(17) 0.061(7) Uiso 1 1 d . . . . .
H7B H 1.216(4) 0.540(2) 0.3710(17) 0.062(7) Uiso 1 1 d . . . . .
C8 C 0.9069(4) 0.69905(18) 0.30046(16) 0.0462(5) Uani 1 1 d . . . . .
H8 H 1.006(4) 0.723(2) 0.3428(17) 0.059(7) Uiso 1 1 d . . . . .
C9 C 0.7313(4) 0.76381(17) 0.24375(15) 0.0419(5) Uani 1 1 d . . . . .
C10 C 0.6405(4) 0.69360(16) 0.19484(13) 0.0373(4) Uani 1 1 d . . . . .
C11 C 0.4665(4) 0.70801(18) 0.12896(14) 0.0417(5) Uani 1 1 d . . . . .
H11 H 0.370(4) 0.7833(19) 0.1020(15) 0.049(6) Uiso 1 1 d . . . . .
C12 C 0.4337(4) 0.6177(2) 0.09737(16) 0.0482(5) Uani 1 1 d . . . . .
H12 H 0.321(4) 0.6240(19) 0.0524(16) 0.052(6) Uiso 1 1 d . . . . .
C13 C 0.5685(4) 0.51301(19) 0.13055(16) 0.0479(5) Uani 1 1 d . . . . .
H13 H 0.541(4) 0.4515(18) 0.1087(14) 0.043(6) Uiso 1 1 d . . . . .
C14 C 0.7389(4) 0.49616(18) 0.19581(15) 0.0418(5) Uani 1 1 d . . . . .
H14 H 0.830(4) 0.424(2) 0.2186(16) 0.057(7) Uiso 1 1 d . . . . .
C15 C 0.7741(3) 0.58739(16) 0.22678(13) 0.0372(4) Uani 1 1 d . . . . .
C16 C 0.4417(4) 1.03727(16) 0.18543(14) 0.0386(4) Uani 1 1 d . . . . .
C17 C 0.2678(4) 1.10204(16) 0.12527(14) 0.0389(4) Uani 1 1 d . . . . .
C18 C 0.1230(5) 1.0718(2) 0.05877(19) 0.0502(5) Uani 1 1 d . . . . .
H18A H -0.060(7) 1.075(3) 0.077(3) 0.124(13) Uiso 1 1 d . . . . .
H18B H 0.166(7) 0.995(3) 0.066(3) 0.122(13) Uiso 1 1 d . . . . .
H18C H 0.161(6) 1.118(3) -0.008(3) 0.120(12) Uiso 1 1 d . . . . .
C19 C 0.0794(5) 1.2997(2) 0.0940(2) 0.0528(6) Uani 1 1 d . . . . .
H19A H -0.095(5) 1.278(2) 0.1205(18) 0.072(8) Uiso 1 1 d . . . . .
H19B H 0.118(5) 1.367(3) 0.106(2) 0.087(9) Uiso 1 1 d . . . . .
H19C H 0.101(6) 1.324(3) 0.021(3) 0.108(11) Uiso 1 1 d . . . . .
C20 C 0.5149(4) 1.10926(17) 0.23361(14) 0.0417(5) Uani 1 1 d . . . . .
C21 C 0.6961(5) 1.0854(2) 0.30674(19) 0.0567(6) Uani 1 1 d . . . . .
H21A H 0.696(4) 1.151(2) 0.3277(17) 0.062(7) Uiso 1 1 d . . . . .
H21B H 0.872(6) 1.067(3) 0.285(2) 0.099(10) Uiso 1 1 d . . . . .
H21C H 0.646(6) 1.018(3) 0.370(2) 0.097(10) 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
N1 C7 1.452(3) . ?
N1 C8 1.361(3) . ?
N1 C15 1.389(3) . ?
N2 N3 1.267(2) . ?
N2 C9 1.405(2) . ?
N3 C16 1.410(2) . ?
N4 N5 1.372(2) . ?
N4 C20 1.331(3) . ?
N5 C17 1.344(2) . ?
N5 C19 1.449(3) . ?
C1 H1 1.01(2) . ?
C1 C2 1.386(3) . ?
C1 C6 1.382(3) . ?
C2 H2 0.99(3) . ?
C2 C3 1.369(5) . ?
C3 H3 1.00(3) . ?
C3 C4 1.364(5) . ?
C4 H4 0.91(3) . ?
C4 C5 1.398(4) . ?
C5 H5 0.95(2) . ?
C5 C6 1.387(3) . ?
C6 C7 1.510(3) . ?
C7 H7A 1.01(2) . ?
C7 H7B 1.01(3) . ?
C8 H8 1.00(2) . ?
C8 C9 1.370(3) . ?
C9 C10 1.451(3) . ?
C10 C11 1.396(3) . ?
C10 C15 1.415(3) . ?
C11 H11 1.01(2) . ?
C11 C12 1.384(3) . ?
C12 H12 0.94(2) . ?
C12 C13 1.406(3) . ?
C13 H13 0.95(2) . ?
C13 C14 1.371(3) . ?
C14 H14 0.96(2) . ?
C14 C15 1.391(3) . ?
C16 C17 1.388(3) . ?
C16 C20 1.424(3) . ?
C17 C18 1.487(3) . ?
C18 H18A 1.00(4) . ?
C18 H18B 0.94(4) . ?
C18 H18C 0.95(4) . ?
C19 H19A 0.98(3) . ?
C19 H19B 0.95(3) . ?
C19 H19C 1.01(3) . ?
C20 C21 1.490(3) . ?
C21 H21A 0.97(3) . ?
C21 H21B 1.01(3) . ?
C21 H21C 1.01(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
C8 N1 C7 125.62(19) . . ?
C8 N1 C15 108.82(17) . . ?
C15 N1 C7 125.38(17) . . ?
N3 N2 C9 112.27(17) . . ?
N2 N3 C16 113.22(17) . . ?
C20 N4 N5 105.22(16) . . ?
N4 N5 C19 120.17(18) . . ?
C17 N5 N4 112.59(16) . . ?
C17 N5 C19 127.16(19) . . ?
C2 C1 H1 119.1(14) . . ?
C6 C1 H1 120.1(14) . . ?
C6 C1 C2 120.7(3) . . ?
C1 C2 H2 121(2) . . ?
C3 C2 C1 120.0(3) . . ?
C3 C2 H2 119.0(19) . . ?
C2 C3 H3 118.2(18) . . ?
C4 C3 C2 120.1(3) . . ?
C4 C3 H3 121.7(19) . . ?
C3 C4 H4 124.3(18) . . ?
C3 C4 C5 120.6(3) . . ?
C5 C4 H4 115.1(18) . . ?
C4 C5 H5 122.9(14) . . ?
C6 C5 C4 119.7(3) . . ?
C6 C5 H5 117.3(14) . . ?
C1 C6 C5 118.9(2) . . ?
C1 C6 C7 118.99(19) . . ?
C5 C6 C7 122.1(2) . . ?
N1 C7 C6 114.44(18) . . ?
N1 C7 H7A 109.7(13) . . ?
N1 C7 H7B 105.6(14) . . ?
C6 C7 H7A 108.8(13) . . ?
C6 C7 H7B 111.6(13) . . ?
H7A C7 H7B 106.3(19) . . ?
N1 C8 H8 122.5(13) . . ?
N1 C8 C9 110.1(2) . . ?
C9 C8 H8 127.4(13) . . ?
N2 C9 C10 132.84(19) . . ?
C8 C9 N2 119.83(19) . . ?
C8 C9 C10 107.32(18) . . ?
C11 C10 C9 135.88(18) . . ?
C11 C10 C15 118.71(18) . . ?
C15 C10 C9 105.41(17) . . ?
C10 C11 H11 122.0(12) . . ?
C12 C11 C10 118.35(19) . . ?
C12 C11 H11 119.6(12) . . ?
C11 C12 H12 121.3(14) . . ?
C11 C12 C13 121.7(2) . . ?
C13 C12 H12 117.0(14) . . ?
C12 C13 H13 120.3(13) . . ?
C14 C13 C12 121.1(2) . . ?
C14 C13 H13 118.6(13) . . ?
C13 C14 H14 121.0(14) . . ?
C13 C14 C15 117.18(19) . . ?
C15 C14 H14 121.8(14) . . ?
N1 C15 C10 108.30(17) . . ?
N1 C15 C14 128.80(18) . . ?
C14 C15 C10 122.90(19) . . ?
N3 C16 C20 135.04(19) . . ?
C17 C16 N3 119.44(18) . . ?
C17 C16 C20 105.52(17) . . ?
N5 C17 C16 106.31(17) . . ?
N5 C17 C18 123.40(19) . . ?
C16 C17 C18 130.28(19) . . ?
C17 C18 H18A 112(2) . . ?
C17 C18 H18B 106(2) . . ?
C17 C18 H18C 115(2) . . ?
H18A C18 H18B 109(3) . . ?
H18A C18 H18C 109(3) . . ?
H18B C18 H18C 106(3) . . ?
N5 C19 H19A 111.3(15) . . ?
N5 C19 H19B 110.8(18) . . ?
N5 C19 H19C 110.3(18) . . ?
H19A C19 H19B 108(2) . . ?
H19A C19 H19C 111(2) . . ?
H19B C19 H19C 106(2) . . ?
N4 C20 C16 110.36(18) . . ?
N4 C20 C21 120.1(2) . . ?
C16 C20 C21 129.5(2) . . ?
C20 C21 H21A 108.8(15) . . ?
C20 C21 H21B 115.7(17) . . ?
C20 C21 H21C 113.9(18) . . ?
H21A C21 H21B 111(2) . . ?
H21A C21 H21C 102(2) . . ?
H21B C21 H21C 105(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
N1 C8 C9 N2 178.50(17) . . . . ?
N1 C8 C9 C10 -0.4(2) . . . . ?
N2 N3 C16 C17 178.96(17) . . . . ?
N2 N3 C16 C20 -0.6(3) . . . . ?
N2 C9 C10 C11 1.5(4) . . . . ?
N2 C9 C10 C15 -178.9(2) . . . . ?
N3 N2 C9 C8 179.34(18) . . . . ?
N3 N2 C9 C10 -2.1(3) . . . . ?
N3 C16 C17 N5 -179.21(16) . . . . ?
N3 C16 C17 C18 1.6(3) . . . . ?
N3 C16 C20 N4 179.5(2) . . . . ?
N3 C16 C20 C21 -0.5(4) . . . . ?
N4 N5 C17 C16 -0.7(2) . . . . ?
N4 N5 C17 C18 178.62(19) . . . . ?
N5 N4 C20 C16 -0.2(2) . . . . ?
N5 N4 C20 C21 179.77(19) . . . . ?
C1 C2 C3 C4 1.1(4) . . . . ?
C1 C6 C7 N1 148.0(2) . . . . ?
C2 C1 C6 C5 -1.7(3) . . . . ?
C2 C1 C6 C7 177.3(2) . . . . ?
C2 C3 C4 C5 -2.0(4) . . . . ?
C3 C4 C5 C6 1.0(4) . . . . ?
C4 C5 C6 C1 0.8(3) . . . . ?
C4 C5 C6 C7 -178.2(2) . . . . ?
C5 C6 C7 N1 -33.0(3) . . . . ?
C6 C1 C2 C3 0.8(4) . . . . ?
C7 N1 C8 C9 176.18(18) . . . . ?
C7 N1 C15 C10 -176.29(17) . . . . ?
C7 N1 C15 C14 4.5(3) . . . . ?
C8 N1 C7 C6 119.8(2) . . . . ?
C8 N1 C15 C10 -0.9(2) . . . . ?
C8 N1 C15 C14 179.87(19) . . . . ?
C8 C9 C10 C11 -179.8(2) . . . . ?
C8 C9 C10 C15 -0.2(2) . . . . ?
C9 N2 N3 C16 179.87(15) . . . . ?
C9 C10 C11 C12 179.3(2) . . . . ?
C9 C10 C15 N1 0.7(2) . . . . ?
C9 C10 C15 C14 179.92(17) . . . . ?
C10 C11 C12 C13 0.6(3) . . . . ?
C11 C10 C15 N1 -179.60(16) . . . . ?
C11 C10 C15 C14 -0.3(3) . . . . ?
C11 C12 C13 C14 -0.1(3) . . . . ?
C12 C13 C14 C15 -0.6(3) . . . . ?
C13 C14 C15 N1 179.93(19) . . . . ?
C13 C14 C15 C10 0.8(3) . . . . ?
C15 N1 C7 C6 -65.6(3) . . . . ?
C15 N1 C8 C9 0.8(2) . . . . ?
C15 C10 C11 C12 -0.4(3) . . . . ?
C17 C16 C20 N4 -0.2(2) . . . . ?
C17 C16 C20 C21 179.8(2) . . . . ?
C19 N5 C17 C16 -177.37(19) . . . . ?
C19 N5 C17 C18 1.9(3) . . . . ?
C20 N4 N5 C17 0.6(2) . . . . ?
C20 N4 N5 C19 177.53(18) . . . . ?
C20 C16 C17 N5 0.5(2) . . . . ?
C20 C16 C17 C18 -178.7(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
