# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# 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_1
_audit_block_doi                 10.5517/ccdc.csd.cc26png1
_database_code_depnum_ccdc_archive 'CCDC 2046603'
loop_
_audit_author_name
_audit_author_address
'Shou Yuan' 'Qingdao University of Science and Technology'
_audit_update_record             
;
2020-11-26 deposited with the CCDC.	2021-06-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H11 N3'
_chemical_formula_weight         269.30

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   15.379(9)
_cell_length_b                   7.516(4)
_cell_length_c                   11.563(6)
_cell_angle_alpha                90
_cell_angle_beta                 100.885(9)
_cell_angle_gamma                90
_cell_volume                     1312.5(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2372
_cell_measurement_theta_min      2.71
_cell_measurement_theta_max      26.62

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            COLORLESS
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.363
_exptl_crystal_F_000             560
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.230
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.210
_exptl_absorpt_coefficient_mu    0.083
_shelx_estimated_absorpt_T_min   0.981
_shelx_estimated_absorpt_T_max   0.983
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7551
_diffrn_reflns_av_unetI/netI     0.0400
_diffrn_reflns_av_R_equivalents  0.0394
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_theta_min         3.028
_diffrn_reflns_theta_max         24.994
_diffrn_reflns_theta_full        24.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             2298
_reflns_number_gt                1752
_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 SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0714P)²+0.2834P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2298
_refine_ls_number_parameters     190
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0624
_refine_ls_R_factor_gt           0.0454
_refine_ls_wR_factor_ref         0.1313
_refine_ls_wR_factor_gt          0.1234
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_restrained_S_all      1.017
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.37905(14) 0.4254(3) 0.19115(17) 0.0446(5) Uani 1 1 d . . . . .
H1A H 0.3744 0.4526 0.1100 0.053 Uiso 1 1 calc R U . . .
C2 C 0.45539(15) 0.3535(3) 0.25415(18) 0.0512(6) Uani 1 1 d . . . . .
H2A H 0.5036 0.3289 0.2160 0.061 Uiso 1 1 calc R U . . .
C3 C 0.46286(14) 0.3163(3) 0.37355(18) 0.0476(5) Uani 1 1 d . . . . .
H3A H 0.5160 0.2649 0.4154 0.057 Uiso 1 1 calc R U . . .
C4 C 0.39517(13) 0.3522(3) 0.43193(16) 0.0397(5) Uani 1 1 d . . . . .
H4A H 0.4012 0.3291 0.5138 0.048 Uiso 1 1 calc R U . . .
C5 C 0.31819(12) 0.4228(2) 0.36838(14) 0.0334(4) Uani 1 1 d . . . . .
C6 C 0.30887(12) 0.4578(2) 0.24730(15) 0.0340(4) Uani 1 1 d . . . . .
C7 C 0.17908(12) 0.5291(3) 0.30601(15) 0.0347(5) Uani 1 1 d . . . . .
C8 C 0.09367(13) 0.5915(3) 0.29862(17) 0.0438(5) Uani 1 1 d . . . . .
H8A H 0.0666 0.5957 0.3659 0.053 Uiso 1 1 calc R U . . .
C9 C 0.04937(14) 0.6472(3) 0.19012(18) 0.0510(6) Uani 1 1 d . . . . .
H9A H -0.0092 0.6917 0.1829 0.061 Uiso 1 1 calc R U . . .
C10 C 0.08770(14) 0.6401(3) 0.09138(18) 0.0513(6) Uani 1 1 d . . . . .
H10A H 0.0546 0.6763 0.0173 0.062 Uiso 1 1 calc R U . . .
C11 C 0.17356(14) 0.5810(3) 0.09941(16) 0.0431(5) Uani 1 1 d . . . . .
H11A H 0.2002 0.5785 0.0317 0.052 Uiso 1 1 calc R U . . .
C12 C 0.22060(12) 0.5252(2) 0.20784(15) 0.0346(5) Uani 1 1 d . . . . .
C13 C 0.22200(12) 0.4564(2) 0.51931(15) 0.0335(5) Uani 1 1 d . . . . .
C14 C 0.27983(12) 0.5263(2) 0.61371(15) 0.0342(4) Uani 1 1 d . . . . .
H14A H 0.3341 0.5794 0.6040 0.041 Uiso 1 1 calc R U . . .
C15 C 0.25629(12) 0.5165(2) 0.72346(14) 0.0346(5) Uani 1 1 d . . . . .
C16 C 0.17585(14) 0.4417(3) 0.73371(16) 0.0428(5) Uani 1 1 d . . . . .
H16A H 0.1599 0.4393 0.8092 0.051 Uiso 1 1 calc R U . . .
C17 C 0.14449(13) 0.3788(3) 0.53922(16) 0.0399(5) Uani 1 1 d . . . . .
H17A H 0.1063 0.3260 0.4741 0.048 Uiso 1 1 calc R U . . .
C18 C 0.31128(13) 0.5880(3) 0.82661(16) 0.0409(5) Uani 1 1 d . . . . .
N1 N 0.23854(10) 0.4648(2) 0.40340(12) 0.0357(4) Uani 1 1 d . . . . .
N2 N 0.11991(11) 0.3732(2) 0.64327(14) 0.0446(5) Uani 1 1 d . . . . .
N3 N 0.35217(13) 0.6447(3) 0.91140(14) 0.0550(5) Uani 1 1 d . . . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.370(3) . ?
C1 C6 1.382(3) . ?
C1 H1A 0.9500 . ?
C2 C3 1.392(3) . ?
C2 H2A 0.9500 . ?
C3 C4 1.370(3) . ?
C3 H3A 0.9500 . ?
C4 C5 1.376(3) . ?
C4 H4A 0.9500 . ?
C5 N1 1.397(2) . ?
C5 C6 1.405(2) . ?
C6 C12 1.440(3) . ?
C7 C8 1.382(3) . ?
C7 N1 1.396(2) . ?
C7 C12 1.404(2) . ?
C8 C9 1.375(3) . ?
C8 H8A 0.9500 . ?
C9 C10 1.381(3) . ?
C9 H9A 0.9500 . ?
C10 C11 1.380(3) . ?
C10 H10A 0.9500 . ?
C11 C12 1.389(3) . ?
C11 H11A 0.9500 . ?
C13 C14 1.375(3) . ?
C13 C17 1.385(3) . ?
C13 N1 1.412(2) . ?
C14 C15 1.386(2) . ?
C14 H14A 0.9500 . ?
C15 C16 1.384(3) . ?
C15 C18 1.430(3) . ?
C16 N2 1.326(3) . ?
C16 H16A 0.9500 . ?
C17 N2 1.328(2) . ?
C17 H17A 0.9500 . ?
C18 N3 1.143(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
C2 C1 C6 119.10(18) . . ?
C2 C1 H1A 120.5 . . ?
C6 C1 H1A 120.5 . . ?
C1 C2 C3 120.56(19) . . ?
C1 C2 H2A 119.7 . . ?
C3 C2 H2A 119.7 . . ?
C4 C3 C2 121.4(2) . . ?
C4 C3 H3A 119.3 . . ?
C2 C3 H3A 119.3 . . ?
C3 C4 C5 118.02(18) . . ?
C3 C4 H4A 121.0 . . ?
C5 C4 H4A 121.0 . . ?
C4 C5 N1 130.18(16) . . ?
C4 C5 C6 121.31(16) . . ?
N1 C5 C6 108.46(16) . . ?
C1 C6 C5 119.57(18) . . ?
C1 C6 C12 133.32(17) . . ?
C5 C6 C12 107.11(15) . . ?
C8 C7 N1 129.60(16) . . ?
C8 C7 C12 121.94(17) . . ?
N1 C7 C12 108.45(16) . . ?
C9 C8 C7 117.46(18) . . ?
C9 C8 H8A 121.3 . . ?
C7 C8 H8A 121.3 . . ?
C8 C9 C10 121.8(2) . . ?
C8 C9 H9A 119.1 . . ?
C10 C9 H9A 119.1 . . ?
C11 C10 C9 120.61(19) . . ?
C11 C10 H10A 119.7 . . ?
C9 C10 H10A 119.7 . . ?
C10 C11 C12 119.13(18) . . ?
C10 C11 H11A 120.4 . . ?
C12 C11 H11A 120.4 . . ?
C11 C12 C7 119.00(18) . . ?
C11 C12 C6 133.75(17) . . ?
C7 C12 C6 107.25(16) . . ?
C14 C13 C17 118.47(16) . . ?
C14 C13 N1 122.08(17) . . ?
C17 C13 N1 119.44(16) . . ?
C13 C14 C15 117.72(18) . . ?
C13 C14 H14A 121.1 . . ?
C15 C14 H14A 121.1 . . ?
C16 C15 C14 119.48(17) . . ?
C16 C15 C18 118.58(16) . . ?
C14 C15 C18 121.90(17) . . ?
N2 C16 C15 123.18(17) . . ?
N2 C16 H16A 118.4 . . ?
C15 C16 H16A 118.4 . . ?
N2 C17 C13 124.41(18) . . ?
N2 C17 H17A 117.8 . . ?
C13 C17 H17A 117.8 . . ?
N3 C18 C15 177.1(2) . . ?
C5 N1 C7 108.73(14) . . ?
C5 N1 C13 126.17(15) . . ?
C7 N1 C13 124.96(16) . . ?
C16 N2 C17 116.67(17) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 -1.1(3) . . . . ?
C1 C2 C3 C4 -0.9(3) . . . . ?
C2 C3 C4 C5 1.5(3) . . . . ?
C3 C4 C5 N1 177.01(19) . . . . ?
C3 C4 C5 C6 -0.2(3) . . . . ?
C2 C1 C6 C5 2.4(3) . . . . ?
C2 C1 C6 C12 -177.8(2) . . . . ?
C4 C5 C6 C1 -1.8(3) . . . . ?
N1 C5 C6 C1 -179.51(17) . . . . ?
C4 C5 C6 C12 178.37(17) . . . . ?
N1 C5 C6 C12 0.6(2) . . . . ?
N1 C7 C8 C9 -179.89(19) . . . . ?
C12 C7 C8 C9 1.3(3) . . . . ?
C7 C8 C9 C10 0.6(3) . . . . ?
C8 C9 C10 C11 -1.9(3) . . . . ?
C9 C10 C11 C12 1.2(3) . . . . ?
C10 C11 C12 C7 0.6(3) . . . . ?
C10 C11 C12 C6 -179.9(2) . . . . ?
C8 C7 C12 C11 -1.9(3) . . . . ?
N1 C7 C12 C11 179.06(16) . . . . ?
C8 C7 C12 C6 178.47(18) . . . . ?
N1 C7 C12 C6 -0.6(2) . . . . ?
C1 C6 C12 C11 0.6(4) . . . . ?
C5 C6 C12 C11 -179.6(2) . . . . ?
C1 C6 C12 C7 -179.9(2) . . . . ?
C5 C6 C12 C7 0.0(2) . . . . ?
C17 C13 C14 C15 -0.8(3) . . . . ?
N1 C13 C14 C15 177.97(16) . . . . ?
C13 C14 C15 C16 -1.4(3) . . . . ?
C13 C14 C15 C18 -178.93(17) . . . . ?
C14 C15 C16 N2 1.9(3) . . . . ?
C18 C15 C16 N2 179.46(19) . . . . ?
C14 C13 C17 N2 2.9(3) . . . . ?
N1 C13 C17 N2 -175.87(18) . . . . ?
C4 C5 N1 C7 -178.5(2) . . . . ?
C6 C5 N1 C7 -1.0(2) . . . . ?
C4 C5 N1 C13 5.7(3) . . . . ?
C6 C5 N1 C13 -176.80(17) . . . . ?
C8 C7 N1 C5 -178.0(2) . . . . ?
C12 C7 N1 C5 1.0(2) . . . . ?
C8 C7 N1 C13 -2.1(3) . . . . ?
C12 C7 N1 C13 176.84(17) . . . . ?
C14 C13 N1 C5 46.8(3) . . . . ?
C17 C13 N1 C5 -134.5(2) . . . . ?
C14 C13 N1 C7 -128.3(2) . . . . ?
C17 C13 N1 C7 50.4(3) . . . . ?
C15 C16 N2 C17 0.1(3) . . . . ?
C13 C17 N2 C16 -2.5(3) . . . . ?

_refine_diff_density_max         0.190
_refine_diff_density_min         -0.161
_refine_diff_density_rms         0.044

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2046605'
loop_
_audit_author_name
_audit_author_address
'Shou Yuan'
;Qingdao University of Science and Technology
China
;
_audit_update_record             
;
2020-11-26 deposited with the CCDC.	2021-06-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        CCCM
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C36 H26 N6 O2'
_chemical_formula_weight         574.63

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   7.8374(11)
_cell_length_b                   25.281(3)
_cell_length_c                   14.813(2)
_cell_angle_alpha                90
_cell_angle_beta                 102.932(3)
_cell_angle_gamma                90
_cell_volume                     2860.6(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    1360
_cell_measurement_theta_min      2.79
_cell_measurement_theta_max      22.03

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            COLORLESS
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.334
_exptl_crystal_F_000             1200
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.140
_exptl_absorpt_coefficient_mu    0.086
_shelx_estimated_absorpt_T_min   0.983
_shelx_estimated_absorpt_T_max   0.988
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14544
_diffrn_reflns_av_unetI/netI     0.1003
_diffrn_reflns_av_R_equivalents  0.0831
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.666
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_full        24.998
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             5035
_reflns_number_gt                3091
_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 SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0845P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5035
_refine_ls_number_parameters     397
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1063
_refine_ls_R_factor_gt           0.0490
_refine_ls_wR_factor_ref         0.1305
_refine_ls_wR_factor_gt          0.1105
_refine_ls_goodness_of_fit_ref   0.782
_refine_ls_restrained_S_all      0.782
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.8441(3) 0.77743(10) 0.71439(18) 0.0210(6) Uani 1 1 d . . . . .
H1 H 0.9418 0.7542 0.7252 0.025 Uiso 1 1 calc R U . . .
C2 C 0.8309(3) 0.81723(11) 0.77650(19) 0.0247(7) Uani 1 1 d . . . . .
H2 H 0.9227 0.8219 0.8299 0.030 Uiso 1 1 calc R U . . .
C3 C 0.6865(4) 0.85061(11) 0.76273(19) 0.0263(7) Uani 1 1 d . . . . .
H3 H 0.6825 0.8782 0.8058 0.032 Uiso 1 1 calc R U . . .
C4 C 0.5482(3) 0.84414(10) 0.68678(19) 0.0241(7) Uani 1 1 d . . . . .
H4 H 0.4481 0.8663 0.6783 0.029 Uiso 1 1 calc R U . . .
C5 C 0.5593(3) 0.80423(10) 0.62296(18) 0.0191(6) Uani 1 1 d . . . . .
C6 C 0.7103(3) 0.77248(10) 0.63597(17) 0.0178(6) Uani 1 1 d . . . . .
C7 C 0.5271(3) 0.74569(10) 0.50159(17) 0.0169(6) Uani 1 1 d . . . . .
C8 C 0.4543(3) 0.72261(10) 0.41679(17) 0.0199(6) Uani 1 1 d . . . . .
H8 H 0.5129 0.6951 0.3922 0.024 Uiso 1 1 calc R U . . .
C9 C 0.2926(3) 0.74123(11) 0.36922(19) 0.0237(6) Uani 1 1 d . . . . .
H9 H 0.2392 0.7259 0.3112 0.028 Uiso 1 1 calc R U . . .
C10 C 0.2066(3) 0.78198(11) 0.40454(19) 0.0248(7) Uani 1 1 d . . . . .
H10 H 0.0958 0.7938 0.3705 0.030 Uiso 1 1 calc R U . . .
C11 C 0.2805(3) 0.80516(11) 0.48814(18) 0.0224(6) Uani 1 1 d . . . . .
H11 H 0.2223 0.8331 0.5119 0.027 Uiso 1 1 calc R U . . .
C12 C 0.4434(3) 0.78682(10) 0.53760(18) 0.0177(6) Uani 1 1 d . . . . .
C13 C 0.8226(3) 0.70180(10) 0.54641(17) 0.0167(6) Uani 1 1 d . . . . .
C14 C 0.9974(3) 0.71685(10) 0.56362(17) 0.0194(6) Uani 1 1 d . . . . .
H14 H 1.0313 0.7515 0.5850 0.023 Uiso 1 1 calc R U . . .
C15 C 1.1207(3) 0.68105(10) 0.54947(17) 0.0193(6) Uani 1 1 d . . . . .
H15 H 1.2412 0.6903 0.5630 0.023 Uiso 1 1 calc R U . . .
C16 C 1.0670(3) 0.63134(10) 0.51531(17) 0.0164(6) Uani 1 1 d . . . . .
C17 C 0.7807(3) 0.65058(10) 0.51451(17) 0.0162(6) Uani 1 1 d . . . . .
H17 H 0.6620 0.6397 0.5045 0.019 Uiso 1 1 calc R U . . .
C18 C 1.1985(3) 0.59319(10) 0.49250(17) 0.0176(6) Uani 1 1 d . . . . .
C19 C 0.5176(3) 0.50947(10) 0.35997(17) 0.0156(6) Uani 1 1 d . . . . .
C20 C 0.6326(3) 0.48867(10) 0.29883(17) 0.0168(6) Uani 1 1 d . . . . .
C21 C 0.5600(3) 0.45810(10) 0.22268(18) 0.0203(6) Uani 1 1 d . . . . .
H21 H 0.4385 0.4501 0.2090 0.024 Uiso 1 1 calc R U . . .
C22 C 0.6652(3) 0.43931(10) 0.16666(18) 0.0205(6) Uani 1 1 d . . . . .
H22 H 0.6174 0.4184 0.1137 0.025 Uiso 1 1 calc R U . . .
C23 C 0.8416(3) 0.45147(10) 0.18912(17) 0.0171(6) Uani 1 1 d . . . . .
C24 C 0.9051(3) 0.48242(10) 0.26699(17) 0.0164(6) Uani 1 1 d . . . . .
H24 H 1.0263 0.4908 0.2820 0.020 Uiso 1 1 calc R U . . .
C25 C 1.1039(3) 0.40041(10) 0.17025(18) 0.0184(6) Uani 1 1 d . . . . .
C26 C 1.1816(3) 0.38670(10) 0.26111(18) 0.0222(6) Uani 1 1 d . . . . .
H26 H 1.1366 0.3991 0.3117 0.027 Uiso 1 1 calc R U . . .
C27 C 1.3266(3) 0.35428(11) 0.2746(2) 0.0261(7) Uani 1 1 d . . . . .
H27 H 1.3843 0.3453 0.3361 0.031 Uiso 1 1 calc R U . . .
C28 C 1.3916(4) 0.33423(11) 0.2011(2) 0.0275(7) Uani 1 1 d . . . . .
H28 H 1.4900 0.3112 0.2131 0.033 Uiso 1 1 calc R U . . .
C29 C 1.3133(3) 0.34777(10) 0.1116(2) 0.0258(7) Uani 1 1 d . . . . .
H29 H 1.3575 0.3343 0.0614 0.031 Uiso 1 1 calc R U . . .
C30 C 1.1690(3) 0.38135(10) 0.09487(18) 0.0194(6) Uani 1 1 d . . . . .
C31 C 1.0565(3) 0.40199(10) 0.01160(18) 0.0192(6) Uani 1 1 d . . . . .
C32 C 1.0557(4) 0.39650(10) -0.08238(19) 0.0249(7) Uani 1 1 d . . . . .
H32 H 1.1430 0.3762 -0.1017 0.030 Uiso 1 1 calc R U . . .
C33 C 0.9257(4) 0.42121(11) -0.14621(19) 0.0281(7) Uani 1 1 d . . . . .
H33 H 0.9215 0.4171 -0.2104 0.034 Uiso 1 1 calc R U . . .
C34 C 0.7996(4) 0.45227(11) -0.11799(19) 0.0263(7) Uani 1 1 d . . . . .
H34 H 0.7129 0.4695 -0.1636 0.032 Uiso 1 1 calc R U . . .
C35 C 0.7974(3) 0.45863(11) -0.02552(18) 0.0239(7) Uani 1 1 d . . . . .
H35 H 0.7114 0.4799 -0.0068 0.029 Uiso 1 1 calc R U . . .
C36 C 0.9263(3) 0.43266(10) 0.03889(17) 0.0186(6) Uani 1 1 d . . . . .
N5 N 0.6909(2) 0.73685(8) 0.56173(14) 0.0169(5) Uani 1 1 d . . . . .
N6 N 0.8977(2) 0.61598(8) 0.49723(14) 0.0168(5) Uani 1 1 d . . . . .
N7 N 1.1335(3) 0.55159(9) 0.44156(14) 0.0229(5) Uani 1 1 d . . . . .
H7A H 1.2044 0.5286 0.4245 0.028 Uiso 1 1 calc R U . . .
H7B H 1.0195 0.5470 0.4249 0.028 Uiso 1 1 calc R U . . .
N8 N 0.5928(3) 0.53908(8) 0.43073(14) 0.0187(5) Uani 1 1 d . . . . .
H8A H 0.5299 0.5525 0.4675 0.022 Uiso 1 1 calc R U . . .
H8B H 0.7059 0.5454 0.4413 0.022 Uiso 1 1 calc R U . . .
N9 N 0.8045(3) 0.50101(8) 0.32181(14) 0.0171(5) Uani 1 1 d . . . . .
N10 N 0.9568(2) 0.43200(8) 0.13587(14) 0.0181(5) Uani 1 1 d . . . . .
O1 O 1.3578(2) 0.60215(7) 0.51856(12) 0.0227(4) Uani 1 1 d . . . . .
O2 O 0.3590(2) 0.49875(7) 0.34059(12) 0.0229(4) Uani 1 1 d . . . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C6 1.385(3) . ?
C1 C2 1.383(4) . ?
C1 H1 0.9500 . ?
C2 C3 1.389(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.386(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.398(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.407(3) . ?
C5 C12 1.451(4) . ?
C6 N5 1.403(3) . ?
C7 C8 1.387(4) . ?
C7 C12 1.398(3) . ?
C7 N5 1.407(3) . ?
C8 C9 1.387(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.396(4) . ?
C9 H9 0.9500 . ?
C10 C11 1.375(4) . ?
C10 H10 0.9500 . ?
C11 C12 1.401(3) . ?
C11 H11 0.9500 . ?
C13 C14 1.390(3) . ?
C13 C17 1.392(3) . ?
C13 N5 1.417(3) . ?
C14 C15 1.374(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.385(3) . ?
C15 H15 0.9500 . ?
C16 N6 1.351(3) . ?
C16 C18 1.504(3) . ?
C17 N6 1.333(3) . ?
C17 H17 0.9500 . ?
C18 O1 1.242(3) . ?
C18 N7 1.328(3) . ?
C19 O2 1.241(3) . ?
C19 N8 1.315(3) . ?
C19 C20 1.508(3) . ?
C20 N9 1.350(3) . ?
C20 C21 1.381(3) . ?
C21 C22 1.378(3) . ?
C21 H21 0.9500 . ?
C22 C23 1.382(3) . ?
C22 H22 0.9500 . ?
C23 C24 1.391(3) . ?
C23 N10 1.414(3) . ?
C24 N9 1.337(3) . ?
C24 H24 0.9500 . ?
C25 C26 1.391(4) . ?
C25 N10 1.401(3) . ?
C25 C30 1.412(3) . ?
C26 C27 1.379(3) . ?
C26 H26 0.9500 . ?
C27 C28 1.396(4) . ?
C27 H27 0.9500 . ?
C28 C29 1.375(4) . ?
C28 H28 0.9500 . ?
C29 C30 1.391(3) . ?
C29 H29 0.9500 . ?
C30 C31 1.444(4) . ?
C31 C32 1.398(4) . ?
C31 C36 1.411(3) . ?
C32 C33 1.376(4) . ?
C32 H32 0.9500 . ?
C33 C34 1.397(4) . ?
C33 H33 0.9500 . ?
C34 C35 1.383(4) . ?
C34 H34 0.9500 . ?
C35 C36 1.389(4) . ?
C35 H35 0.9500 . ?
C36 N10 1.403(3) . ?
N7 H7A 0.8800 . ?
N7 H7B 0.8800 . ?
N8 H8A 0.8800 . ?
N8 H8B 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
C6 C1 C2 117.9(2) . . ?
C6 C1 H1 121.0 . . ?
C2 C1 H1 121.0 . . ?
C1 C2 C3 121.6(3) . . ?
C1 C2 H2 119.2 . . ?
C3 C2 H2 119.2 . . ?
C4 C3 C2 120.7(3) . . ?
C4 C3 H3 119.6 . . ?
C2 C3 H3 119.6 . . ?
C3 C4 C5 118.6(3) . . ?
C3 C4 H4 120.7 . . ?
C5 C4 H4 120.7 . . ?
C4 C5 C6 119.8(2) . . ?
C4 C5 C12 133.4(2) . . ?
C6 C5 C12 106.9(2) . . ?
C1 C6 N5 130.1(2) . . ?
C1 C6 C5 121.3(2) . . ?
N5 C6 C5 108.6(2) . . ?
C8 C7 C12 121.7(2) . . ?
C8 C7 N5 129.7(2) . . ?
C12 C7 N5 108.5(2) . . ?
C9 C8 C7 117.5(2) . . ?
C9 C8 H8 121.3 . . ?
C7 C8 H8 121.3 . . ?
C8 C9 C10 121.5(3) . . ?
C8 C9 H9 119.2 . . ?
C10 C9 H9 119.2 . . ?
C11 C10 C9 120.7(2) . . ?
C11 C10 H10 119.7 . . ?
C9 C10 H10 119.7 . . ?
C10 C11 C12 118.8(2) . . ?
C10 C11 H11 120.6 . . ?
C12 C11 H11 120.6 . . ?
C11 C12 C7 119.8(2) . . ?
C11 C12 C5 132.5(2) . . ?
C7 C12 C5 107.6(2) . . ?
C14 C13 C17 117.7(2) . . ?
C14 C13 N5 121.5(2) . . ?
C17 C13 N5 120.8(2) . . ?
C15 C14 C13 119.3(2) . . ?
C15 C14 H14 120.3 . . ?
C13 C14 H14 120.3 . . ?
C14 C15 C16 119.2(2) . . ?
C14 C15 H15 120.4 . . ?
C16 C15 H15 120.4 . . ?
N6 C16 C15 122.5(2) . . ?
N6 C16 C18 117.6(2) . . ?
C15 C16 C18 119.8(2) . . ?
N6 C17 C13 123.8(2) . . ?
N6 C17 H17 118.1 . . ?
C13 C17 H17 118.1 . . ?
O1 C18 N7 123.5(2) . . ?
O1 C18 C16 120.3(2) . . ?
N7 C18 C16 116.1(2) . . ?
O2 C19 N8 123.7(2) . . ?
O2 C19 C20 119.1(2) . . ?
N8 C19 C20 117.1(2) . . ?
N9 C20 C21 122.7(2) . . ?
N9 C20 C19 117.7(2) . . ?
C21 C20 C19 119.6(2) . . ?
C20 C21 C22 119.5(2) . . ?
C20 C21 H21 120.3 . . ?
C22 C21 H21 120.3 . . ?
C23 C22 C21 118.6(2) . . ?
C23 C22 H22 120.7 . . ?
C21 C22 H22 120.7 . . ?
C22 C23 C24 118.6(2) . . ?
C22 C23 N10 121.2(2) . . ?
C24 C23 N10 120.3(2) . . ?
N9 C24 C23 123.5(2) . . ?
N9 C24 H24 118.3 . . ?
C23 C24 H24 118.3 . . ?
C26 C25 N10 129.8(2) . . ?
C26 C25 C30 121.5(2) . . ?
N10 C25 C30 108.7(2) . . ?
C27 C26 C25 117.1(2) . . ?
C27 C26 H26 121.4 . . ?
C25 C26 H26 121.4 . . ?
C26 C27 C28 122.4(3) . . ?
C26 C27 H27 118.8 . . ?
C28 C27 H27 118.8 . . ?
C29 C28 C27 120.0(3) . . ?
C29 C28 H28 120.0 . . ?
C27 C28 H28 120.0 . . ?
C28 C29 C30 119.5(3) . . ?
C28 C29 H29 120.2 . . ?
C30 C29 H29 120.2 . . ?
C29 C30 C25 119.4(3) . . ?
C29 C30 C31 133.6(2) . . ?
C25 C30 C31 107.0(2) . . ?
C32 C31 C36 119.8(2) . . ?
C32 C31 C30 132.9(2) . . ?
C36 C31 C30 107.3(2) . . ?
C33 C32 C31 118.5(2) . . ?
C33 C32 H32 120.8 . . ?
C31 C32 H32 120.8 . . ?
C32 C33 C34 121.0(3) . . ?
C32 C33 H33 119.5 . . ?
C34 C33 H33 119.5 . . ?
C35 C34 C33 121.9(3) . . ?
C35 C34 H34 119.1 . . ?
C33 C34 H34 119.1 . . ?
C34 C35 C36 117.2(2) . . ?
C34 C35 H35 121.4 . . ?
C36 C35 H35 121.4 . . ?
C35 C36 N10 129.8(2) . . ?
C35 C36 C31 121.6(2) . . ?
N10 C36 C31 108.6(2) . . ?
C6 N5 C7 108.5(2) . . ?
C6 N5 C13 124.9(2) . . ?
C7 N5 C13 126.3(2) . . ?
C17 N6 C16 117.4(2) . . ?
C18 N7 H7A 120.0 . . ?
C18 N7 H7B 120.0 . . ?
H7A N7 H7B 120.0 . . ?
C19 N8 H8A 120.0 . . ?
C19 N8 H8B 120.0 . . ?
H8A N8 H8B 120.0 . . ?
C24 N9 C20 117.1(2) . . ?
C36 N10 C25 108.5(2) . . ?
C36 N10 C23 125.7(2) . . ?
C25 N10 C23 124.9(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
C6 C1 C2 C3 1.6(4) . . . . ?
C1 C2 C3 C4 1.6(4) . . . . ?
C2 C3 C4 C5 -1.7(4) . . . . ?
C3 C4 C5 C6 -1.2(4) . . . . ?
C3 C4 C5 C12 -179.5(3) . . . . ?
C2 C1 C6 N5 178.9(2) . . . . ?
C2 C1 C6 C5 -4.7(4) . . . . ?
C4 C5 C6 C1 4.5(4) . . . . ?
C12 C5 C6 C1 -176.8(2) . . . . ?
C4 C5 C6 N5 -178.3(2) . . . . ?
C12 C5 C6 N5 0.4(3) . . . . ?
C12 C7 C8 C9 -1.1(4) . . . . ?
N5 C7 C8 C9 -176.3(2) . . . . ?
C7 C8 C9 C10 0.6(4) . . . . ?
C8 C9 C10 C11 0.2(4) . . . . ?
C9 C10 C11 C12 -0.5(4) . . . . ?
C10 C11 C12 C7 0.0(4) . . . . ?
C10 C11 C12 C5 175.8(3) . . . . ?
C8 C7 C12 C11 0.8(4) . . . . ?
N5 C7 C12 C11 176.9(2) . . . . ?
C8 C7 C12 C5 -175.9(2) . . . . ?
N5 C7 C12 C5 0.1(3) . . . . ?
C4 C5 C12 C11 1.9(5) . . . . ?
C6 C5 C12 C11 -176.5(3) . . . . ?
C4 C5 C12 C7 178.1(3) . . . . ?
C6 C5 C12 C7 -0.3(3) . . . . ?
C17 C13 C14 C15 -0.5(4) . . . . ?
N5 C13 C14 C15 178.7(2) . . . . ?
C13 C14 C15 C16 2.2(4) . . . . ?
C14 C15 C16 N6 -1.6(4) . . . . ?
C14 C15 C16 C18 175.3(2) . . . . ?
C14 C13 C17 N6 -2.0(4) . . . . ?
N5 C13 C17 N6 178.8(2) . . . . ?
N6 C16 C18 O1 -170.5(2) . . . . ?
C15 C16 C18 O1 12.4(4) . . . . ?
N6 C16 C18 N7 11.5(3) . . . . ?
C15 C16 C18 N7 -165.5(2) . . . . ?
O2 C19 C20 N9 -180.0(2) . . . . ?
N8 C19 C20 N9 1.2(3) . . . . ?
O2 C19 C20 C21 -0.1(4) . . . . ?
N8 C19 C20 C21 -178.9(2) . . . . ?
N9 C20 C21 C22 -0.4(4) . . . . ?
C19 C20 C21 C22 179.7(2) . . . . ?
C20 C21 C22 C23 0.5(4) . . . . ?
C21 C22 C23 C24 -0.4(4) . . . . ?
C21 C22 C23 N10 178.1(2) . . . . ?
C22 C23 C24 N9 0.2(4) . . . . ?
N10 C23 C24 N9 -178.2(2) . . . . ?
N10 C25 C26 C27 179.6(2) . . . . ?
C30 C25 C26 C27 0.9(4) . . . . ?
C25 C26 C27 C28 -2.0(4) . . . . ?
C26 C27 C28 C29 1.7(4) . . . . ?
C27 C28 C29 C30 -0.2(4) . . . . ?
C28 C29 C30 C25 -0.9(4) . . . . ?
C28 C29 C30 C31 -178.4(3) . . . . ?
C26 C25 C30 C29 0.5(4) . . . . ?
N10 C25 C30 C29 -178.4(2) . . . . ?
C26 C25 C30 C31 178.6(2) . . . . ?
N10 C25 C30 C31 -0.3(3) . . . . ?
C29 C30 C31 C32 -1.9(5) . . . . ?
C25 C30 C31 C32 -179.7(3) . . . . ?
C29 C30 C31 C36 177.5(3) . . . . ?
C25 C30 C31 C36 -0.3(3) . . . . ?
C36 C31 C32 C33 -0.4(4) . . . . ?
C30 C31 C32 C33 178.9(3) . . . . ?
C31 C32 C33 C34 1.6(4) . . . . ?
C32 C33 C34 C35 -1.4(4) . . . . ?
C33 C34 C35 C36 -0.1(4) . . . . ?
C34 C35 C36 N10 179.7(2) . . . . ?
C34 C35 C36 C31 1.4(4) . . . . ?
C32 C31 C36 C35 -1.1(4) . . . . ?
C30 C31 C36 C35 179.4(2) . . . . ?
C32 C31 C36 N10 -179.7(2) . . . . ?
C30 C31 C36 N10 0.8(3) . . . . ?
C1 C6 N5 C7 176.5(2) . . . . ?
C5 C6 N5 C7 -0.3(3) . . . . ?
C1 C6 N5 C13 -9.2(4) . . . . ?
C5 C6 N5 C13 174.0(2) . . . . ?
C8 C7 N5 C6 175.7(3) . . . . ?
C12 C7 N5 C6 0.1(3) . . . . ?
C8 C7 N5 C13 1.5(4) . . . . ?
C12 C7 N5 C13 -174.1(2) . . . . ?
C14 C13 N5 C6 -38.3(4) . . . . ?
C17 C13 N5 C6 140.8(2) . . . . ?
C14 C13 N5 C7 135.0(3) . . . . ?
C17 C13 N5 C7 -45.9(3) . . . . ?
C13 C17 N6 C16 2.6(4) . . . . ?
C15 C16 N6 C17 -0.7(3) . . . . ?
C18 C16 N6 C17 -177.7(2) . . . . ?
C23 C24 N9 C20 -0.2(4) . . . . ?
C21 C20 N9 C24 0.2(4) . . . . ?
C19 C20 N9 C24 -179.9(2) . . . . ?
C35 C36 N10 C25 -179.4(2) . . . . ?
C31 C36 N10 C25 -0.9(3) . . . . ?
C35 C36 N10 C23 11.3(4) . . . . ?
C31 C36 N10 C23 -170.2(2) . . . . ?
C26 C25 N10 C36 -178.0(3) . . . . ?
C30 C25 N10 C36 0.7(3) . . . . ?
C26 C25 N10 C23 -8.6(4) . . . . ?
C30 C25 N10 C23 170.1(2) . . . . ?
C22 C23 N10 C36 46.5(4) . . . . ?
C24 C23 N10 C36 -135.0(3) . . . . ?
C22 C23 N10 C25 -121.0(3) . . . . ?
C24 C23 N10 C25 57.4(3) . . . . ?

_refine_diff_density_max         0.218
_refine_diff_density_min         -0.273
_refine_diff_density_rms         0.054

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 2053954'
loop_
_audit_author_name
_audit_author_address
'Shou yuan'
;Qingdao University of Science amd Technology
China
;
_audit_update_record             
;
2021-01-05 deposited with the CCDC.	2021-06-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H13 N3 O'
_chemical_formula_weight         287.31

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

_cell_length_a                   9.4696(11)
_cell_length_b                   5.0807(6)
_cell_length_c                   29.630(4)
_cell_angle_alpha                90
_cell_angle_beta                 96.439(2)
_cell_angle_gamma                90
_cell_volume                     1416.6(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    4037
_cell_measurement_theta_min      2.77
_cell_measurement_theta_max      27.52

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.347
_exptl_crystal_F_000             600
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.290
_exptl_crystal_size_min          0.280
_exptl_absorpt_coefficient_mu    0.087
_shelx_estimated_absorpt_T_min   0.975
_shelx_estimated_absorpt_T_max   0.976
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6703
_diffrn_reflns_av_unetI/netI     0.0192
_diffrn_reflns_av_R_equivalents  0.0172
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_theta_min         2.767
_diffrn_reflns_theta_max         24.996
_diffrn_reflns_theta_full        24.996
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             2475
_reflns_number_gt                2250
_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 SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0654P)²+0.4918P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2475
_refine_ls_number_parameters     199
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0395
_refine_ls_R_factor_gt           0.0354
_refine_ls_wR_factor_ref         0.1003
_refine_ls_wR_factor_gt          0.0973
_refine_ls_goodness_of_fit_ref   0.993
_refine_ls_restrained_S_all      0.993
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.09134(15) -0.2051(3) 0.32281(5) 0.0211(3) Uani 1 1 d . . . . .
H1 H 0.0792 -0.3313 0.2990 0.025 Uiso 1 1 calc R U . . .
C2 C -0.01617(15) -0.1585(3) 0.34975(5) 0.0242(3) Uani 1 1 d . . . . .
H2 H -0.1031 -0.2528 0.3444 0.029 Uiso 1 1 calc R U . . .
C3 C 0.00261(15) 0.0274(3) 0.38482(5) 0.0230(3) Uani 1 1 d . . . . .
H3 H -0.0722 0.0557 0.4031 0.028 Uiso 1 1 calc R U . . .
C4 C 0.12701(14) 0.1713(3) 0.39367(5) 0.0194(3) Uani 1 1 d . . . . .
H4 H 0.1385 0.2960 0.4177 0.023 Uiso 1 1 calc R U . . .
C5 C 0.23493(13) 0.1265(3) 0.36605(4) 0.0155(3) Uani 1 1 d . . . . .
C6 C 0.21842(13) -0.0633(3) 0.33118(4) 0.0163(3) Uani 1 1 d . . . . .
C7 C 0.44392(14) 0.1071(3) 0.33466(4) 0.0163(3) Uani 1 1 d . . . . .
C8 C 0.57958(14) 0.1504(3) 0.32176(4) 0.0208(3) Uani 1 1 d . . . . .
H8 H 0.6410 0.2800 0.3364 0.025 Uiso 1 1 calc R U . . .
C9 C 0.62130(15) -0.0033(3) 0.28673(5) 0.0239(3) Uani 1 1 d . . . . .
H9 H 0.7131 0.0219 0.2774 0.029 Uiso 1 1 calc R U . . .
C10 C 0.53153(15) -0.1942(3) 0.26478(5) 0.0231(3) Uani 1 1 d . . . . .
H10 H 0.5641 -0.2990 0.2415 0.028 Uiso 1 1 calc R U . . .
C11 C 0.39613(15) -0.2313(3) 0.27674(4) 0.0206(3) Uani 1 1 d . . . . .
H11 H 0.3346 -0.3588 0.2615 0.025 Uiso 1 1 calc R U . . .
C12 C 0.35112(14) -0.0778(3) 0.31165(4) 0.0168(3) Uani 1 1 d . . . . .
C13 C 0.43759(14) 0.4037(3) 0.40218(4) 0.0154(3) Uani 1 1 d . . . . .
C14 C 0.36112(13) 0.6133(3) 0.41842(4) 0.0160(3) Uani 1 1 d . . . . .
H14 H 0.2647 0.6356 0.4063 0.019 Uiso 1 1 calc R U . . .
C15 C 0.55365(14) 0.7532(3) 0.46609(4) 0.0157(3) Uani 1 1 d . . . . .
H15 H 0.5950 0.8754 0.4880 0.019 Uiso 1 1 calc R U . . .
C16 C 0.63825(13) 0.5512(3) 0.45220(4) 0.0145(3) Uani 1 1 d . . . . .
C17 C 0.57814(13) 0.3699(3) 0.42063(4) 0.0153(3) Uani 1 1 d . . . . .
H17 H 0.6321 0.2250 0.4118 0.018 Uiso 1 1 calc R U . . .
C18 C 0.79021(13) 0.5194(3) 0.47177(4) 0.0145(3) Uani 1 1 d . . . . .
N1 N 0.37312(11) 0.2321(2) 0.36824(4) 0.0160(3) Uani 1 1 d . . . . .
N2 N 0.41651(12) 0.7832(2) 0.45002(4) 0.0172(3) Uani 1 1 d . . . . .
N3 N 0.85866(11) 0.7343(2) 0.48746(4) 0.0179(3) Uani 1 1 d . . . . .
H3A H 0.9481 0.7240 0.4992 0.021 Uiso 1 1 calc R U . . .
H3B H 0.8146 0.8871 0.4862 0.021 Uiso 1 1 calc R U . . .
O1 O 0.84721(9) 0.29798(18) 0.47275(3) 0.0190(2) Uani 1 1 d . . . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.383(2) . ?
C1 C6 1.4007(19) . ?
C1 H1 0.9500 . ?
C2 C3 1.401(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.386(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.3977(19) . ?
C4 H4 0.9500 . ?
C5 N1 1.4090(17) . ?
C5 C6 1.4093(18) . ?
C6 C12 1.4430(19) . ?
C7 C8 1.3982(19) . ?
C7 C12 1.4088(19) . ?
C7 N1 1.4115(17) . ?
C8 C9 1.391(2) . ?
C8 H8 0.9500 . ?
C9 C10 1.401(2) . ?
C9 H9 0.9500 . ?
C10 C11 1.381(2) . ?
C10 H10 0.9500 . ?
C11 C12 1.3998(19) . ?
C11 H11 0.9500 . ?
C13 C17 1.3917(18) . ?
C13 C14 1.4026(19) . ?
C13 N1 1.4167(16) . ?
C14 N2 1.3368(17) . ?
C14 H14 0.9500 . ?
C15 N2 1.3409(17) . ?
C15 C16 1.3922(18) . ?
C15 H15 0.9500 . ?
C16 C17 1.3888(18) . ?
C16 C18 1.4986(17) . ?
C17 H17 0.9500 . ?
C18 O1 1.2467(16) . ?
C18 N3 1.3268(17) . ?
N3 H3A 0.8800 . ?
N3 H3B 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 C1 C6 118.91(13) . . ?
C2 C1 H1 120.5 . . ?
C6 C1 H1 120.5 . . ?
C1 C2 C3 120.22(13) . . ?
C1 C2 H2 119.9 . . ?
C3 C2 H2 119.9 . . ?
C4 C3 C2 122.04(13) . . ?
C4 C3 H3 119.0 . . ?
C2 C3 H3 119.0 . . ?
C3 C4 C5 117.71(13) . . ?
C3 C4 H4 121.1 . . ?
C5 C4 H4 121.1 . . ?
C4 C5 N1 130.35(12) . . ?
C4 C5 C6 120.83(12) . . ?
N1 C5 C6 108.68(11) . . ?
C1 C6 C5 120.28(12) . . ?
C1 C6 C12 132.26(13) . . ?
C5 C6 C12 107.39(11) . . ?
C8 C7 C12 121.01(12) . . ?
C8 C7 N1 130.20(12) . . ?
C12 C7 N1 108.74(11) . . ?
C9 C8 C7 117.52(13) . . ?
C9 C8 H8 121.2 . . ?
C7 C8 H8 121.2 . . ?
C8 C9 C10 121.79(13) . . ?
C8 C9 H9 119.1 . . ?
C10 C9 H9 119.1 . . ?
C11 C10 C9 120.54(13) . . ?
C11 C10 H10 119.7 . . ?
C9 C10 H10 119.7 . . ?
C10 C11 C12 118.80(13) . . ?
C10 C11 H11 120.6 . . ?
C12 C11 H11 120.6 . . ?
C11 C12 C7 120.27(12) . . ?
C11 C12 C6 132.51(12) . . ?
C7 C12 C6 107.22(11) . . ?
C17 C13 C14 117.83(12) . . ?
C17 C13 N1 121.31(11) . . ?
C14 C13 N1 120.86(11) . . ?
N2 C14 C13 123.61(12) . . ?
N2 C14 H14 118.2 . . ?
C13 C14 H14 118.2 . . ?
N2 C15 C16 123.05(12) . . ?
N2 C15 H15 118.5 . . ?
C16 C15 H15 118.5 . . ?
C17 C16 C15 118.83(12) . . ?
C17 C16 C18 119.49(11) . . ?
C15 C16 C18 121.64(12) . . ?
C16 C17 C13 118.96(12) . . ?
C16 C17 H17 120.5 . . ?
C13 C17 H17 120.5 . . ?
O1 C18 N3 122.75(11) . . ?
O1 C18 C16 120.05(11) . . ?
N3 C18 C16 117.20(11) . . ?
C5 N1 C7 107.96(10) . . ?
C5 N1 C13 126.23(11) . . ?
C7 N1 C13 125.20(11) . . ?
C14 N2 C15 117.62(11) . . ?
C18 N3 H3A 120.0 . . ?
C18 N3 H3B 120.0 . . ?
H3A N3 H3B 120.0 . . ?

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
C6 C1 C2 C3 -0.2(2) . . . . ?
C1 C2 C3 C4 0.5(2) . . . . ?
C2 C3 C4 C5 0.4(2) . . . . ?
C3 C4 C5 N1 -176.60(13) . . . . ?
C3 C4 C5 C6 -1.52(19) . . . . ?
C2 C1 C6 C5 -1.0(2) . . . . ?
C2 C1 C6 C12 175.32(13) . . . . ?
C4 C5 C6 C1 1.87(19) . . . . ?
N1 C5 C6 C1 177.91(12) . . . . ?
C4 C5 C6 C12 -175.28(12) . . . . ?
N1 C5 C6 C12 0.77(14) . . . . ?
C12 C7 C8 C9 -2.59(19) . . . . ?
N1 C7 C8 C9 -179.40(13) . . . . ?
C7 C8 C9 C10 0.3(2) . . . . ?
C8 C9 C10 C11 1.6(2) . . . . ?
C9 C10 C11 C12 -1.0(2) . . . . ?
C10 C11 C12 C7 -1.29(19) . . . . ?
C10 C11 C12 C6 178.29(13) . . . . ?
C8 C7 C12 C11 3.16(19) . . . . ?
N1 C7 C12 C11 -179.41(11) . . . . ?
C8 C7 C12 C6 -176.52(12) . . . . ?
N1 C7 C12 C6 0.92(14) . . . . ?
C1 C6 C12 C11 2.7(3) . . . . ?
C5 C6 C12 C11 179.34(13) . . . . ?
C1 C6 C12 C7 -177.70(14) . . . . ?
C5 C6 C12 C7 -1.04(14) . . . . ?
C17 C13 C14 N2 1.00(19) . . . . ?
N1 C13 C14 N2 -179.28(11) . . . . ?
N2 C15 C16 C17 -0.76(19) . . . . ?
N2 C15 C16 C18 -178.40(11) . . . . ?
C15 C16 C17 C13 3.29(18) . . . . ?
C18 C16 C17 C13 -179.02(11) . . . . ?
C14 C13 C17 C16 -3.38(18) . . . . ?
N1 C13 C17 C16 176.90(11) . . . . ?
C17 C16 C18 O1 -24.47(17) . . . . ?
C15 C16 C18 O1 153.16(13) . . . . ?
C17 C16 C18 N3 155.44(12) . . . . ?
C15 C16 C18 N3 -26.93(17) . . . . ?
C4 C5 N1 C7 175.33(13) . . . . ?
C6 C5 N1 C7 -0.21(14) . . . . ?
C4 C5 N1 C13 3.9(2) . . . . ?
C6 C5 N1 C13 -171.64(11) . . . . ?
C8 C7 N1 C5 176.67(13) . . . . ?
C12 C7 N1 C5 -0.45(14) . . . . ?
C8 C7 N1 C13 -11.8(2) . . . . ?
C12 C7 N1 C13 171.09(11) . . . . ?
C17 C13 N1 C5 137.27(13) . . . . ?
C14 C13 N1 C5 -42.44(18) . . . . ?
C17 C13 N1 C7 -32.74(18) . . . . ?
C14 C13 N1 C7 147.55(13) . . . . ?
C13 C14 N2 C15 1.50(19) . . . . ?
C16 C15 N2 C14 -1.63(19) . . . . ?

_refine_diff_density_max         0.175
_refine_diff_density_min         -0.241
_refine_diff_density_rms         0.046

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1_CCDC3
_database_code_depnum_ccdc_archive 'CCDC 2056175'
loop_
_audit_author_name
_audit_author_address
' Yaguang Wang'
;Qingdao University of Science amd Technology
China
;
_audit_update_record             
;
2021-01-14 deposited with the CCDC.	2021-06-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H11 N3'
_chemical_formula_weight         269.30

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

_cell_length_a                   9.034(3)
_cell_length_b                   7.442(2)
_cell_length_c                   20.076(6)
_cell_angle_alpha                90
_cell_angle_beta                 99.057(6)
_cell_angle_gamma                90
_cell_volume                     1333.0(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    1434
_cell_measurement_theta_min      2.35
_cell_measurement_theta_max      24.45

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.342
_exptl_crystal_F_000             560
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    0.082
_shelx_estimated_absorpt_T_min   0.979
_shelx_estimated_absorpt_T_max   0.985
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6452
_diffrn_reflns_av_unetI/netI     0.0519
_diffrn_reflns_av_R_equivalents  0.0419
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.647
_diffrn_reflns_theta_max         24.992
_diffrn_reflns_theta_full        24.992
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2339
_reflns_number_gt                1650
_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 SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0743P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.010(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2339
_refine_ls_number_parameters     191
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0724
_refine_ls_R_factor_gt           0.0461
_refine_ls_wR_factor_ref         0.1301
_refine_ls_wR_factor_gt          0.1118
_refine_ls_goodness_of_fit_ref   0.991
_refine_ls_restrained_S_all      0.991
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.9180(2) 0.6354(3) 0.91236(11) 0.0475(6) Uani 1 1 d . . . . .
H1A H 1.0178 0.6750 0.9268 0.057 Uiso 1 1 calc R U . . .
C2 C 0.8699(2) 0.6060(2) 0.84472(10) 0.0388(5) Uani 1 1 d . . . . .
H2A H 0.9346 0.6259 0.8124 0.047 Uiso 1 1 calc R U . . .
C3 C 0.7239(2) 0.5465(2) 0.82518(9) 0.0324(5) Uani 1 1 d . . . . .
C4 C 0.49598(19) 0.4600(2) 0.76781(9) 0.0304(5) Uani 1 1 d . . . . .
C5 C 0.3778(2) 0.4034(2) 0.71943(10) 0.0358(5) Uani 1 1 d . . . . .
H5A H 0.3854 0.4038 0.6728 0.043 Uiso 1 1 calc R U . . .
C6 C 0.2491(2) 0.3467(2) 0.74201(10) 0.0408(5) Uani 1 1 d . . . . .
H6A H 0.1673 0.3059 0.7100 0.049 Uiso 1 1 calc R U . . .
C7 C 0.2348(2) 0.3472(3) 0.80999(11) 0.0456(6) Uani 1 1 d . . . . .
H7A H 0.1442 0.3076 0.8237 0.055 Uiso 1 1 calc R U . . .
C8 C 0.3516(2) 0.4049(3) 0.85723(10) 0.0436(5) Uani 1 1 d . . . . .
H8A H 0.3422 0.4067 0.9037 0.052 Uiso 1 1 calc R U . . .
C9 C 0.4842(2) 0.4608(2) 0.83650(9) 0.0336(5) Uani 1 1 d . . . . .
C10 C 0.6275(2) 0.5187(2) 0.87286(10) 0.0353(5) Uani 1 1 d . . . . .
C11 C 0.6792(2) 0.5512(3) 0.94048(10) 0.0456(5) Uani 1 1 d . . . . .
H11A H 0.6149 0.5340 0.9731 0.055 Uiso 1 1 calc R U . . .
C12 C 0.8240(2) 0.6084(3) 0.96003(11) 0.0516(6) Uani 1 1 d . . . . .
H12A H 0.8601 0.6297 1.0064 0.062 Uiso 1 1 calc R U . . .
C13 C 0.6947(2) 0.5383(2) 0.69857(9) 0.0315(5) Uani 1 1 d . . . . .
C14 C 0.8396(2) 0.4914(2) 0.69017(10) 0.0375(5) Uani 1 1 d . . . . .
H14A H 0.9080 0.4441 0.7268 0.045 Uiso 1 1 calc R U . . .
C15 C 0.8819(2) 0.5147(3) 0.62803(10) 0.0406(5) Uani 1 1 d . . . . .
H15A H 0.9805 0.4855 0.6209 0.049 Uiso 1 1 calc R U . . .
C16 C 0.7776(2) 0.5817(3) 0.57590(10) 0.0412(5) Uani 1 1 d . . . . .
C17 C 0.6362(2) 0.6233(3) 0.58897(10) 0.0436(5) Uani 1 1 d . . . . .
H17A H 0.5648 0.6675 0.5528 0.052 Uiso 1 1 calc R U . . .
C18 C 0.8115(3) 0.6064(3) 0.50894(12) 0.0564(6) Uani 1 1 d . . . . .
N1 N 0.64318(16) 0.51306(19) 0.76067(7) 0.0326(4) Uani 1 1 d . . . . .
N2 N 0.59358(17) 0.6052(2) 0.64926(8) 0.0394(4) Uani 1 1 d . . . . .
N3 N 0.8337(3) 0.6284(3) 0.45484(11) 0.0833(8) Uani 1 1 d . . . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.376(3) . ?
C1 C12 1.391(3) . ?
C1 H1A 0.9500 . ?
C2 C3 1.388(3) . ?
C2 H2A 0.9500 . ?
C3 N1 1.405(2) . ?
C3 C10 1.407(2) . ?
C4 C5 1.391(3) . ?
C4 C9 1.399(2) . ?
C4 N1 1.416(2) . ?
C5 C6 1.379(2) . ?
C5 H5A 0.9500 . ?
C6 C7 1.391(3) . ?
C6 H6A 0.9500 . ?
C7 C8 1.372(3) . ?
C7 H7A 0.9500 . ?
C8 C9 1.392(3) . ?
C8 H8A 0.9500 . ?
C9 C10 1.448(3) . ?
C10 C11 1.386(3) . ?
C11 C12 1.372(3) . ?
C11 H11A 0.9500 . ?
C12 H12A 0.9500 . ?
C13 N2 1.333(2) . ?
C13 C14 1.390(3) . ?
C13 N1 1.411(2) . ?
C14 C15 1.372(3) . ?
C14 H14A 0.9500 . ?
C15 C16 1.386(3) . ?
C15 H15A 0.9500 . ?
C16 C17 1.379(3) . ?
C16 C18 1.437(3) . ?
C17 N2 1.333(2) . ?
C17 H17A 0.9500 . ?
C18 N3 1.147(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
C2 C1 C12 121.6(2) . . ?
C2 C1 H1A 119.2 . . ?
C12 C1 H1A 119.2 . . ?
C1 C2 C3 117.85(19) . . ?
C1 C2 H2A 121.1 . . ?
C3 C2 H2A 121.1 . . ?
C2 C3 N1 130.48(17) . . ?
C2 C3 C10 121.15(18) . . ?
N1 C3 C10 108.29(16) . . ?
C5 C4 C9 121.36(16) . . ?
C5 C4 N1 130.07(16) . . ?
C9 C4 N1 108.46(15) . . ?
C6 C5 C4 117.22(18) . . ?
C6 C5 H5A 121.4 . . ?
C4 C5 H5A 121.4 . . ?
C5 C6 C7 122.37(19) . . ?
C5 C6 H6A 118.8 . . ?
C7 C6 H6A 118.8 . . ?
C8 C7 C6 119.90(18) . . ?
C8 C7 H7A 120.0 . . ?
C6 C7 H7A 120.0 . . ?
C7 C8 C9 119.44(19) . . ?
C7 C8 H8A 120.3 . . ?
C9 C8 H8A 120.3 . . ?
C8 C9 C4 119.70(17) . . ?
C8 C9 C10 132.92(18) . . ?
C4 C9 C10 107.33(15) . . ?
C11 C10 C3 119.42(18) . . ?
C11 C10 C9 133.08(18) . . ?
C3 C10 C9 107.49(17) . . ?
C12 C11 C10 119.59(19) . . ?
C12 C11 H11A 120.2 . . ?
C10 C11 H11A 120.2 . . ?
C11 C12 C1 120.4(2) . . ?
C11 C12 H12A 119.8 . . ?
C1 C12 H12A 119.8 . . ?
N2 C13 C14 123.51(17) . . ?
N2 C13 N1 115.01(15) . . ?
C14 C13 N1 121.46(17) . . ?
C15 C14 C13 118.72(19) . . ?
C15 C14 H14A 120.6 . . ?
C13 C14 H14A 120.6 . . ?
C14 C15 C16 118.62(18) . . ?
C14 C15 H15A 120.7 . . ?
C16 C15 H15A 120.7 . . ?
C17 C16 C15 118.48(17) . . ?
C17 C16 C18 119.30(19) . . ?
C15 C16 C18 122.22(18) . . ?
N2 C17 C16 123.93(19) . . ?
N2 C17 H17A 118.0 . . ?
C16 C17 H17A 118.0 . . ?
N3 C18 C16 177.7(2) . . ?
C3 N1 C13 126.54(15) . . ?
C3 N1 C4 108.39(14) . . ?
C13 N1 C4 124.95(15) . . ?
C13 N2 C17 116.72(16) . . ?

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
C12 C1 C2 C3 -0.6(3) . . . . ?
C1 C2 C3 N1 176.96(17) . . . . ?
C1 C2 C3 C10 0.6(3) . . . . ?
C9 C4 C5 C6 -0.5(3) . . . . ?
N1 C4 C5 C6 175.19(16) . . . . ?
C4 C5 C6 C7 0.8(3) . . . . ?
C5 C6 C7 C8 -0.3(3) . . . . ?
C6 C7 C8 C9 -0.6(3) . . . . ?
C7 C8 C9 C4 0.9(3) . . . . ?
C7 C8 C9 C10 -176.21(19) . . . . ?
C5 C4 C9 C8 -0.3(3) . . . . ?
N1 C4 C9 C8 -176.89(16) . . . . ?
C5 C4 C9 C10 177.47(16) . . . . ?
N1 C4 C9 C10 0.92(19) . . . . ?
C2 C3 C10 C11 -0.1(3) . . . . ?
N1 C3 C10 C11 -177.12(16) . . . . ?
C2 C3 C10 C9 178.90(16) . . . . ?
N1 C3 C10 C9 1.84(19) . . . . ?
C8 C9 C10 C11 -5.5(4) . . . . ?
C4 C9 C10 C11 177.1(2) . . . . ?
C8 C9 C10 C3 175.69(19) . . . . ?
C4 C9 C10 C3 -1.71(19) . . . . ?
C3 C10 C11 C12 -0.6(3) . . . . ?
C9 C10 C11 C12 -179.2(2) . . . . ?
C10 C11 C12 C1 0.6(3) . . . . ?
C2 C1 C12 C11 0.0(3) . . . . ?
N2 C13 C14 C15 0.0(3) . . . . ?
N1 C13 C14 C15 178.24(16) . . . . ?
C13 C14 C15 C16 -0.9(3) . . . . ?
C14 C15 C16 C17 0.5(3) . . . . ?
C14 C15 C16 C18 -178.57(18) . . . . ?
C15 C16 C17 N2 0.9(3) . . . . ?
C18 C16 C17 N2 179.98(19) . . . . ?
C2 C3 N1 C13 -1.8(3) . . . . ?
C10 C3 N1 C13 174.93(15) . . . . ?
C2 C3 N1 C4 -177.98(18) . . . . ?
C10 C3 N1 C4 -1.29(19) . . . . ?
N2 C13 N1 C3 -140.55(17) . . . . ?
C14 C13 N1 C3 41.1(2) . . . . ?
N2 C13 N1 C4 35.1(2) . . . . ?
C14 C13 N1 C4 -143.28(18) . . . . ?
C5 C4 N1 C3 -175.94(17) . . . . ?
C9 C4 N1 C3 0.21(18) . . . . ?
C5 C4 N1 C13 7.8(3) . . . . ?
C9 C4 N1 C13 -176.08(15) . . . . ?
C14 C13 N2 C17 1.3(3) . . . . ?
N1 C13 N2 C17 -177.05(15) . . . . ?
C16 C17 N2 C13 -1.7(3) . . . . ?

_refine_diff_density_max         0.182
_refine_diff_density_min         -0.183
_refine_diff_density_rms         0.043

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1_CCDC4
_database_code_depnum_ccdc_archive 'CCDC 2056176'
loop_
_audit_author_name
_audit_author_address
'Yaguang Wang'
;Qingdao University of Science amd Technology
China
;
_audit_update_record             
;
2021-01-14 deposited with the CCDC.	2021-06-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H13 N3 O'
_chemical_formula_weight         287.31

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

_cell_length_a                   8.543(8)
_cell_length_b                   10.702(9)
_cell_length_c                   16.886(15)
_cell_angle_alpha                90
_cell_angle_beta                 91.104(17)
_cell_angle_gamma                90
_cell_volume                     1544(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    1705
_cell_measurement_theta_min      2.69
_cell_measurement_theta_max      26.48

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            COLORLESS
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.236
_exptl_crystal_F_000             600
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    0.079
_shelx_estimated_absorpt_T_min   0.983
_shelx_estimated_absorpt_T_max   0.986
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8643
_diffrn_reflns_av_unetI/netI     0.1121
_diffrn_reflns_av_R_equivalents  0.0933
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.652
_diffrn_reflns_theta_max         27.561
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.953
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.953
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.953
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             3394
_reflns_number_gt                1771
_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 SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.1761P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.033(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3394
_refine_ls_number_parameters     200
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1594
_refine_ls_R_factor_gt           0.0886
_refine_ls_wR_factor_ref         0.2893
_refine_ls_wR_factor_gt          0.2268
_refine_ls_goodness_of_fit_ref   0.971
_refine_ls_restrained_S_all      0.971
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.1484(5) 0.4664(5) 0.2760(3) 0.0771(13) Uani 1 1 d . . . . .
H1A H 0.0796 0.4174 0.2438 0.093 Uiso 1 1 calc R U . . .
C2 C 0.2999(4) 0.4248(4) 0.2916(2) 0.0562(10) Uani 1 1 d . . . . .
H2A H 0.3364 0.3479 0.2708 0.067 Uiso 1 1 calc R U . . .
C3 C 0.3953(4) 0.4993(3) 0.33848(19) 0.0446(9) Uani 1 1 d . . . . .
C4 C 0.5970(4) 0.5760(3) 0.41506(18) 0.0461(9) Uani 1 1 d . . . . .
C5 C 0.7384(5) 0.5963(4) 0.4549(2) 0.0600(10) Uani 1 1 d . . . . .
H5A H 0.8195 0.5357 0.4540 0.072 Uiso 1 1 calc R U . . .
C6 C 0.7575(6) 0.7062(5) 0.4955(3) 0.0811(14) Uani 1 1 d . . . . .
H6A H 0.8531 0.7212 0.5236 0.097 Uiso 1 1 calc R U . . .
C7 C 0.6402(8) 0.7965(5) 0.4967(3) 0.0877(16) Uani 1 1 d . . . . .
H7A H 0.6573 0.8727 0.5244 0.105 Uiso 1 1 calc R U . . .
C8 C 0.4991(6) 0.7759(4) 0.4577(3) 0.0756(14) Uani 1 1 d . . . . .
H8A H 0.4192 0.8376 0.4588 0.091 Uiso 1 1 calc R U . . .
C9 C 0.4737(5) 0.6646(3) 0.4168(2) 0.0537(10) Uani 1 1 d . . . . .
C10 C 0.3445(4) 0.6135(3) 0.3701(2) 0.0523(10) Uani 1 1 d . . . . .
C11 C 0.1898(5) 0.6520(4) 0.3538(3) 0.0726(13) Uani 1 1 d . . . . .
H11A H 0.1515 0.7279 0.3753 0.087 Uiso 1 1 calc R U . . .
C12 C 0.0962(5) 0.5801(5) 0.3073(3) 0.0851(15) Uani 1 1 d . . . . .
H12A H -0.0076 0.6072 0.2955 0.102 Uiso 1 1 calc R U . . .
C13 C 0.6476(3) 0.3806(3) 0.33826(18) 0.0371(7) Uani 1 1 d . . . . .
C14 C 0.7518(4) 0.2834(3) 0.23041(18) 0.0427(8) Uani 1 1 d . . . . .
H14A H 0.7622 0.2771 0.1746 0.051 Uiso 1 1 calc R U . . .
C15 C 0.8323(4) 0.1991(3) 0.27752(18) 0.0407(8) Uani 1 1 d . . . . .
H15A H 0.8967 0.1371 0.2544 0.049 Uiso 1 1 calc R U . . .
C16 C 0.8180(3) 0.2059(3) 0.35965(18) 0.0369(8) Uani 1 1 d . . . . .
C17 C 0.7252(4) 0.3013(3) 0.39004(18) 0.0401(8) Uani 1 1 d . . . . .
H17A H 0.7155 0.3114 0.4456 0.048 Uiso 1 1 calc R U . . .
C18 C 0.8938(4) 0.1170(3) 0.41751(18) 0.0405(8) Uani 1 1 d . . . . .
N1 N 0.5486(3) 0.4764(2) 0.36671(15) 0.0422(7) Uani 1 1 d . . . . .
N2 N 0.6594(3) 0.3740(2) 0.25876(14) 0.0402(7) Uani 1 1 d . . . . .
N3 N 0.9550(3) 0.0121(3) 0.39012(16) 0.0518(8) Uani 1 1 d . . . . .
H3A H 0.9992 -0.0417 0.4231 0.062 Uiso 1 1 calc R U . . .
H3B H 0.9515 -0.0039 0.3390 0.062 Uiso 1 1 calc R U . . .
O1 O 0.8964(3) 0.1432(2) 0.48954(13) 0.0581(8) Uani 1 1 d . . . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.390(5) . ?
C1 C12 1.404(6) . ?
C1 H1A 0.9500 . ?
C2 C3 1.379(5) . ?
C2 H2A 0.9500 . ?
C3 N1 1.406(4) . ?
C3 C10 1.406(5) . ?
C4 C5 1.388(5) . ?
C4 N1 1.400(4) . ?
C4 C9 1.418(5) . ?
C5 C6 1.369(6) . ?
C5 H5A 0.9500 . ?
C6 C7 1.393(7) . ?
C6 H6A 0.9500 . ?
C7 C8 1.380(7) . ?
C7 H7A 0.9500 . ?
C8 C9 1.392(5) . ?
C8 H8A 0.9500 . ?
C9 C10 1.451(5) . ?
C10 C11 1.407(6) . ?
C11 C12 1.351(7) . ?
C11 H11A 0.9500 . ?
C12 H12A 0.9500 . ?
C13 N2 1.350(4) . ?
C13 C17 1.379(4) . ?
C13 N1 1.419(4) . ?
C14 N2 1.345(4) . ?
C14 C15 1.378(4) . ?
C14 H14A 0.9500 . ?
C15 C16 1.397(4) . ?
C15 H15A 0.9500 . ?
C16 C17 1.396(4) . ?
C16 C18 1.502(4) . ?
C17 H17A 0.9500 . ?
C18 O1 1.248(4) . ?
C18 N3 1.326(4) . ?
N3 H3A 0.8800 . ?
N3 H3B 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 C1 C12 120.5(4) . . ?
C2 C1 H1A 119.8 . . ?
C12 C1 H1A 119.8 . . ?
C3 C2 C1 117.6(4) . . ?
C3 C2 H2A 121.2 . . ?
C1 C2 H2A 121.2 . . ?
C2 C3 N1 129.1(3) . . ?
C2 C3 C10 122.5(3) . . ?
N1 C3 C10 108.4(3) . . ?
C5 C4 N1 130.2(3) . . ?
C5 C4 C9 121.7(4) . . ?
N1 C4 C9 108.1(3) . . ?
C6 C5 C4 118.1(4) . . ?
C6 C5 H5A 120.9 . . ?
C4 C5 H5A 120.9 . . ?
C5 C6 C7 121.6(5) . . ?
C5 C6 H6A 119.2 . . ?
C7 C6 H6A 119.2 . . ?
C8 C7 C6 120.3(4) . . ?
C8 C7 H7A 119.9 . . ?
C6 C7 H7A 119.9 . . ?
C7 C8 C9 120.0(5) . . ?
C7 C8 H8A 120.0 . . ?
C9 C8 H8A 120.0 . . ?
C8 C9 C4 118.3(4) . . ?
C8 C9 C10 134.6(4) . . ?
C4 C9 C10 107.1(3) . . ?
C11 C10 C3 118.5(4) . . ?
C11 C10 C9 134.2(4) . . ?
C3 C10 C9 107.3(3) . . ?
C12 C11 C10 119.3(4) . . ?
C12 C11 H11A 120.3 . . ?
C10 C11 H11A 120.3 . . ?
C11 C12 C1 121.6(4) . . ?
C11 C12 H12A 119.2 . . ?
C1 C12 H12A 119.2 . . ?
N2 C13 C17 123.6(3) . . ?
N2 C13 N1 115.5(3) . . ?
C17 C13 N1 120.8(3) . . ?
N2 C14 C15 123.8(3) . . ?
N2 C14 H14A 118.1 . . ?
C15 C14 H14A 118.1 . . ?
C14 C15 C16 119.1(3) . . ?
C14 C15 H15A 120.4 . . ?
C16 C15 H15A 120.4 . . ?
C15 C16 C17 117.7(3) . . ?
C15 C16 C18 124.6(3) . . ?
C17 C16 C18 117.7(3) . . ?
C13 C17 C16 119.1(3) . . ?
C13 C17 H17A 120.4 . . ?
C16 C17 H17A 120.4 . . ?
O1 C18 N3 122.0(3) . . ?
O1 C18 C16 119.4(3) . . ?
N3 C18 C16 118.5(3) . . ?
C4 N1 C3 109.1(3) . . ?
C4 N1 C13 125.2(3) . . ?
C3 N1 C13 124.6(3) . . ?
C14 N2 C13 116.6(3) . . ?
C18 N3 H3A 120.0 . . ?
C18 N3 H3B 120.0 . . ?
H3A N3 H3B 120.0 . . ?

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
C12 C1 C2 C3 -0.1(6) . . . . ?
C1 C2 C3 N1 176.1(3) . . . . ?
C1 C2 C3 C10 0.0(5) . . . . ?
N1 C4 C5 C6 176.8(3) . . . . ?
C9 C4 C5 C6 -1.0(5) . . . . ?
C4 C5 C6 C7 -0.7(6) . . . . ?
C5 C6 C7 C8 1.3(7) . . . . ?
C6 C7 C8 C9 -0.2(6) . . . . ?
C7 C8 C9 C4 -1.3(5) . . . . ?
C7 C8 C9 C10 -179.3(4) . . . . ?
C5 C4 C9 C8 2.0(5) . . . . ?
N1 C4 C9 C8 -176.2(3) . . . . ?
C5 C4 C9 C10 -179.5(3) . . . . ?
N1 C4 C9 C10 2.3(3) . . . . ?
C2 C3 C10 C11 0.8(5) . . . . ?
N1 C3 C10 C11 -176.1(3) . . . . ?
C2 C3 C10 C9 179.1(3) . . . . ?
N1 C3 C10 C9 2.3(3) . . . . ?
C8 C9 C10 C11 -6.7(7) . . . . ?
C4 C9 C10 C11 175.2(4) . . . . ?
C8 C9 C10 C3 175.3(4) . . . . ?
C4 C9 C10 C3 -2.8(4) . . . . ?
C3 C10 C11 C12 -1.4(6) . . . . ?
C9 C10 C11 C12 -179.2(4) . . . . ?
C10 C11 C12 C1 1.3(7) . . . . ?
C2 C1 C12 C11 -0.5(7) . . . . ?
N2 C14 C15 C16 0.4(5) . . . . ?
C14 C15 C16 C17 -1.8(5) . . . . ?
C14 C15 C16 C18 177.4(3) . . . . ?
N2 C13 C17 C16 -1.9(5) . . . . ?
N1 C13 C17 C16 178.2(3) . . . . ?
C15 C16 C17 C13 2.5(5) . . . . ?
C18 C16 C17 C13 -176.8(3) . . . . ?
C15 C16 C18 O1 167.7(3) . . . . ?
C17 C16 C18 O1 -13.1(5) . . . . ?
C15 C16 C18 N3 -12.9(5) . . . . ?
C17 C16 C18 N3 166.3(3) . . . . ?
C5 C4 N1 C3 -178.9(3) . . . . ?
C9 C4 N1 C3 -0.9(3) . . . . ?
C5 C4 N1 C13 -10.2(5) . . . . ?
C9 C4 N1 C13 167.8(3) . . . . ?
C2 C3 N1 C4 -177.5(3) . . . . ?
C10 C3 N1 C4 -0.9(3) . . . . ?
C2 C3 N1 C13 13.8(5) . . . . ?
C10 C3 N1 C13 -169.7(3) . . . . ?
N2 C13 N1 C4 -117.9(3) . . . . ?
C17 C13 N1 C4 62.0(4) . . . . ?
N2 C13 N1 C3 49.1(4) . . . . ?
C17 C13 N1 C3 -131.0(3) . . . . ?
C15 C14 N2 C13 0.2(5) . . . . ?
C17 C13 N2 C14 0.5(5) . . . . ?
N1 C13 N2 C14 -179.6(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N3 H3A O1 0.88 2.03 2.898(4) 171.3 3_756
N3 H3B N2 0.88 2.30 3.060(4) 145.3 2_645

_refine_diff_density_max         0.381
_refine_diff_density_min         -0.331
_refine_diff_density_rms         0.083

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1_CCDC5
_database_code_depnum_ccdc_archive 'CCDC 2046606'
loop_
_audit_author_name
_audit_author_address
'Shou Yuan'
;Qingdao University of Science and Technology
China
;
_audit_update_record             
;
2020-11-26 deposited with the CCDC.	2021-06-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H11 N3'
_chemical_formula_weight         269.30

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   18.140(14)
_cell_length_b                   3.914(3)
_cell_length_c                   18.577(14)
_cell_angle_alpha                90
_cell_angle_beta                 95.169(16)
_cell_angle_gamma                90
_cell_volume                     1313.6(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    798
_cell_measurement_theta_min      2.25
_cell_measurement_theta_max      23.43

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            COLORLESS
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.362
_exptl_crystal_F_000             560
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.230
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.160
_exptl_absorpt_coefficient_mu    0.083
_shelx_estimated_absorpt_T_min   0.981
_shelx_estimated_absorpt_T_max   0.987
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5999
_diffrn_reflns_av_unetI/netI     0.1307
_diffrn_reflns_av_R_equivalents  0.1182
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.562
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_full        24.997
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             2302
_reflns_number_gt                1278
_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 SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.1129P)²+0.1985P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.055(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2302
_refine_ls_number_parameters     201
_refine_ls_number_restraints     24
_refine_ls_R_factor_all          0.1483
_refine_ls_R_factor_gt           0.0919
_refine_ls_wR_factor_ref         0.2585
_refine_ls_wR_factor_gt          0.2380
_refine_ls_goodness_of_fit_ref   1.122
_refine_ls_restrained_S_all      1.171
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.0955(3) 0.2461(12) -0.0146(3) 0.0475(13) Uani 1 1 d . . . . .
H1A H 0.0442 0.2310 -0.0084 0.057 Uiso 1 1 calc R U . . .
C2 C 0.1225(3) 0.1343(12) -0.0777(3) 0.0520(14) Uani 1 1 d . . . . .
H2A H 0.0894 0.0385 -0.1147 0.062 Uiso 1 1 calc R U . . .
C3 C 0.1964(3) 0.1588(12) -0.0879(2) 0.0495(14) Uani 1 1 d . . . . .
H3A H 0.2135 0.0812 -0.1319 0.059 Uiso 1 1 calc R U . . .
C4 C 0.2460(3) 0.2953(13) -0.0348(2) 0.0470(13) Uani 1 1 d . . . . .
H4A H 0.2972 0.3098 -0.0415 0.056 Uiso 1 1 calc R U . . .
C5 C 0.2194(2) 0.4105(11) 0.0285(2) 0.0351(11) Uani 1 1 d . . . . .
C6 C 0.1448(3) 0.3810(10) 0.0395(2) 0.0355(11) Uani 1 1 d . . . . .
C7 C 0.2061(2) 0.6164(11) 0.1409(2) 0.0347(11) Uani 1 1 d . . . . .
C8 C 0.2159(3) 0.7740(12) 0.2084(2) 0.0411(12) Uani 1 1 d . . . . .
H8A H 0.2634 0.8471 0.2285 0.049 Uiso 1 1 calc R U . . .
C9 C 0.1535(3) 0.8189(12) 0.2448(3) 0.0473(13) Uani 1 1 d . . . . .
H9A H 0.1584 0.9256 0.2909 0.057 Uiso 1 1 calc R U . . .
C10 C 0.0840(3) 0.7141(13) 0.2165(3) 0.0510(14) Uani 1 1 d . . . . .
H10A H 0.0426 0.7442 0.2438 0.061 Uiso 1 1 calc R U . . .
C11 C 0.0745(3) 0.5667(13) 0.1491(3) 0.0468(13) Uani 1 1 d . . . . .
H11A H 0.0267 0.4984 0.1292 0.056 Uiso 1 1 calc R U . . .
C12 C 0.1361(2) 0.5193(11) 0.1106(2) 0.0350(11) Uani 1 1 d . . . . .
C13 C 0.3352(2) 0.5966(12) 0.1027(2) 0.0393(12) Uani 1 1 d . . . . .
C14 C 0.3753(3) 0.7284(13) 0.0501(2) 0.0444(13) Uani 1 1 d . . . . .
H14A H 0.3502 0.7858 0.0046 0.053 Uiso 1 1 calc R U . . .
N2 N 0.4496(3) 0.7802(15) 0.0604(3) 0.0772(16) Uani 1 1 d . . . . .
C15 C 0.4826(3) 0.6843(19) 0.1271(3) 0.0732(19) Uani 1 1 d . U . . .
C17 C 0.3730(3) 0.5070(13) 0.1692(2) 0.0461(13) Uani 1 1 d . . . . .
H17A H 0.3460 0.4158 0.2063 0.055 Uiso 1 1 calc R U . . .
C18 C 0.5616(4) 0.730(3) 0.1408(4) 0.119(3) Uani 1 1 d . U . . .
N1 N 0.2583(2) 0.5496(9) 0.09049(17) 0.0366(10) Uani 1 1 d . . . . .
C16 C 0.4458(2) 0.5472(14) 0.1813(2) 0.0493(14) Uani 1 1 d . . . . .
H16 H 0.4715 0.4829 0.2261 0.059 Uiso 1 1 calc R U . . .
N3' N 0.6265(7) 0.644(8) 0.1636(7) 0.086(8) Uani 0.48(3) 1 d . U P A 2
N3 N 0.6194(7) 0.930(7) 0.1405(9) 0.088(9) Uani 0.52(3) 1 d . U P A 1


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C6 1.388(6) . ?
C1 C2 1.381(7) . ?
C1 H1A 0.9500 . ?
C2 C3 1.373(7) . ?
C2 H2A 0.9500 . ?
C3 C4 1.381(7) . ?
C3 H3A 0.9500 . ?
C4 C5 1.385(6) . ?
C4 H4A 0.9500 . ?
C5 C6 1.393(6) . ?
C5 N1 1.404(5) . ?
C6 C12 1.449(6) . ?
C7 C8 1.394(6) . ?
C7 C12 1.395(6) . ?
C7 N1 1.415(5) . ?
C8 C9 1.381(7) . ?
C8 H8A 0.9500 . ?
C9 C10 1.384(7) . ?
C9 H9A 0.9500 . ?
C10 C11 1.374(7) . ?
C10 H10A 0.9500 . ?
C11 C12 1.391(6) . ?
C11 H11A 0.9500 . ?
C13 C14 1.370(6) . ?
C13 C17 1.402(6) . ?
C13 N1 1.406(5) . ?
C14 N2 1.359(6) . ?
C14 H14A 0.9500 . ?
N2 C15 1.380(8) . ?
C15 C16 1.366(8) . ?
C15 C18 1.443(9) . ?
C17 C16 1.330(6) . ?
C17 H17A 0.9500 . ?
C18 N3' 1.260(16) . ?
C18 N3 1.309(17) . ?
C16 H16 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
C6 C1 C2 118.7(5) . . ?
C6 C1 H1A 120.6 . . ?
C2 C1 H1A 120.6 . . ?
C3 C2 C1 121.3(5) . . ?
C3 C2 H2A 119.3 . . ?
C1 C2 H2A 119.3 . . ?
C2 C3 C4 120.6(5) . . ?
C2 C3 H3A 119.7 . . ?
C4 C3 H3A 119.7 . . ?
C3 C4 C5 118.6(5) . . ?
C3 C4 H4A 120.7 . . ?
C5 C4 H4A 120.7 . . ?
C4 C5 C6 121.0(4) . . ?
C4 C5 N1 129.4(4) . . ?
C6 C5 N1 109.5(4) . . ?
C1 C6 C5 119.8(4) . . ?
C1 C6 C12 133.4(4) . . ?
C5 C6 C12 106.9(4) . . ?
C8 C7 C12 121.5(4) . . ?
C8 C7 N1 129.7(4) . . ?
C12 C7 N1 108.7(4) . . ?
C9 C8 C7 116.8(5) . . ?
C9 C8 H8A 121.6 . . ?
C7 C8 H8A 121.6 . . ?
C8 C9 C10 122.4(5) . . ?
C8 C9 H9A 118.8 . . ?
C10 C9 H9A 118.8 . . ?
C11 C10 C9 120.3(4) . . ?
C11 C10 H10A 119.8 . . ?
C9 C10 H10A 119.8 . . ?
C10 C11 C12 118.9(5) . . ?
C10 C11 H11A 120.5 . . ?
C12 C11 H11A 120.5 . . ?
C11 C12 C7 120.0(4) . . ?
C11 C12 C6 132.6(4) . . ?
C7 C12 C6 107.5(4) . . ?
C14 C13 C17 118.3(4) . . ?
C14 C13 N1 121.1(4) . . ?
C17 C13 N1 120.6(4) . . ?
N2 C14 C13 122.6(4) . . ?
N2 C14 H14A 118.7 . . ?
C13 C14 H14A 118.7 . . ?
C14 N2 C15 115.5(5) . . ?
C16 C15 N2 124.6(5) . . ?
C16 C15 C18 117.5(6) . . ?
N2 C15 C18 117.9(6) . . ?
C16 C17 C13 121.3(4) . . ?
C16 C17 H17A 119.4 . . ?
C13 C17 H17A 119.4 . . ?
N3' C18 C15 155.3(17) . . ?
N3 C18 C15 148.9(17) . . ?
C13 N1 C5 126.9(4) . . ?
C13 N1 C7 125.6(3) . . ?
C5 N1 C7 107.4(4) . . ?
C17 C16 C15 117.7(4) . . ?
C17 C16 H16 121.1 . . ?
C15 C16 H16 121.1 . . ?

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
C6 C1 C2 C3 -0.9(7) . . . . ?
C1 C2 C3 C4 0.4(7) . . . . ?
C2 C3 C4 C5 -0.8(7) . . . . ?
C3 C4 C5 C6 1.8(7) . . . . ?
C3 C4 C5 N1 178.2(4) . . . . ?
C2 C1 C6 C5 1.9(7) . . . . ?
C2 C1 C6 C12 179.9(4) . . . . ?
C4 C5 C6 C1 -2.4(6) . . . . ?
N1 C5 C6 C1 -179.4(4) . . . . ?
C4 C5 C6 C12 179.1(4) . . . . ?
N1 C5 C6 C12 2.1(5) . . . . ?
C12 C7 C8 C9 2.1(6) . . . . ?
N1 C7 C8 C9 177.1(4) . . . . ?
C7 C8 C9 C10 0.0(7) . . . . ?
C8 C9 C10 C11 -1.7(7) . . . . ?
C9 C10 C11 C12 1.2(7) . . . . ?
C10 C11 C12 C7 0.9(7) . . . . ?
C10 C11 C12 C6 -178.7(4) . . . . ?
C8 C7 C12 C11 -2.6(6) . . . . ?
N1 C7 C12 C11 -178.5(4) . . . . ?
C8 C7 C12 C6 177.1(4) . . . . ?
N1 C7 C12 C6 1.1(5) . . . . ?
C1 C6 C12 C11 -0.6(8) . . . . ?
C5 C6 C12 C11 177.6(5) . . . . ?
C1 C6 C12 C7 179.8(5) . . . . ?
C5 C6 C12 C7 -2.0(5) . . . . ?
C17 C13 C14 N2 -1.1(8) . . . . ?
N1 C13 C14 N2 179.4(5) . . . . ?
C13 C14 N2 C15 1.3(8) . . . . ?
C14 N2 C15 C16 -0.3(9) . . . . ?
C14 N2 C15 C18 179.3(7) . . . . ?
C14 C13 C17 C16 -0.1(8) . . . . ?
N1 C13 C17 C16 179.4(5) . . . . ?
C16 C15 C18 N3' 44(2) . . . . ?
N2 C15 C18 N3' -136.1(19) . . . . ?
C16 C15 C18 N3 -128.7(14) . . . . ?
N2 C15 C18 N3 51.6(16) . . . . ?
C14 C13 N1 C5 44.3(7) . . . . ?
C17 C13 N1 C5 -135.3(5) . . . . ?
C14 C13 N1 C7 -139.8(5) . . . . ?
C17 C13 N1 C7 40.7(6) . . . . ?
C4 C5 N1 C13 -1.5(7) . . . . ?
C6 C5 N1 C13 175.2(4) . . . . ?
C4 C5 N1 C7 -178.1(4) . . . . ?
C6 C5 N1 C7 -1.4(5) . . . . ?
C8 C7 N1 C13 8.0(7) . . . . ?
C12 C7 N1 C13 -176.5(4) . . . . ?
C8 C7 N1 C5 -175.4(4) . . . . ?
C12 C7 N1 C5 0.1(4) . . . . ?
C13 C17 C16 C15 1.0(8) . . . . ?
N2 C15 C16 C17 -0.8(9) . . . . ?
C18 C15 C16 C17 179.5(6) . . . . ?

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
C17 H17A N3 0.95 2.86 3.538(16) 129.3 2_645
C4 H4A N3' 0.95 2.77 3.483(14) 132.8 3_665
C4 H4A N3' 0.95 2.77 3.483(14) 132.8 3_665
C17 H17A N3 0.95 2.86 3.538(16) 129.3 2_645
C4 H4A N3' 0.95 2.77 3.483(14) 132.8 3_665
C17 H17A N3 0.95 2.86 3.538(16) 129.3 2_645
C4 H4A N3' 0.95 2.77 3.483(14) 132.8 3_665
C17 H17A N3 0.95 2.86 3.538(16) 129.3 2_645
C4 H4A N3 0.95 2.66 3.386(12) 134.0 3_665
C17 H17A N3' 0.95 2.65 3.415(15) 138.3 2_645
C4 H4A N3 0.95 2.66 3.386(12) 134.0 3_665
C17 H17A N3' 0.95 2.65 3.415(15) 138.3 2_645
C4 H4A N3 0.95 2.66 3.386(12) 134.0 3_665
C17 H17A N3' 0.95 2.65 3.415(15) 138.3 2_645
C4 H4A N3 0.95 2.66 3.386(12) 134.0 3_665
C17 H17A N3' 0.95 2.65 3.415(15) 138.3 2_645

_refine_diff_density_max         0.466
_refine_diff_density_min         -0.351
_refine_diff_density_rms         0.070

