# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_Compound2j
_database_code_depnum_ccdc_archive 'CCDC 1956320'
loop_
_audit_author_name
_audit_author_address
'Deguang Huang'
;Fujian Institute of Research on the Structure of Matter, CAS
China
;
_audit_update_record             
;
2019-09-27 deposited with the CCDC.	2020-01-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H18 N2 O2'
_chemical_formula_sum            'C18 H18 N2 O2'
_chemical_formula_weight         294.34

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'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1
_symmetry_space_group_name_Hall  '-P 1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.5587(4)
_cell_length_b                   8.8898(7)
_cell_length_c                   12.5059(7)
_cell_angle_alpha                74.341(6)
_cell_angle_beta                 74.736(5)
_cell_angle_gamma                67.915(6)
_cell_volume                     737.35(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    5345
_cell_measurement_theta_min      3.8490
_cell_measurement_theta_max      29.1390

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.326
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             312
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9617
_exptl_absorpt_correction_T_max  0.9827
_exptl_absorpt_process_details   
; 
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018) 
Empirical absorption correction using spherical harmonics, 
 implemented in SCALE3 ABSPACK scaling algorithm. 
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'SuperNova (Mo) X-ray Source'
_diffrn_radiation_monochromator  Mirror
_diffrn_measurement_device_type  'SuperNova, Dual'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.5594
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            15001
_diffrn_reflns_av_R_equivalents  0.0503
_diffrn_reflns_av_sigmaI/netI    0.0358
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.44
_diffrn_reflns_theta_max         26.50
_reflns_number_total             3055
_reflns_number_gt                2577
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0328P)²+0.5096P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3055
_refine_ls_number_parameters     199
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0535
_refine_ls_R_factor_gt           0.0448
_refine_ls_wR_factor_ref         0.1089
_refine_ls_wR_factor_gt          0.1028
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_restrained_S_all      1.070
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.20321(16) 1.14549(14) 1.03289(9) 0.0201(3) Uani 1 1 d . . .
O2 O 0.06828(16) 0.26681(14) 0.58394(10) 0.0209(3) Uani 1 1 d . . .
N1 N 0.7579(2) 0.70520(18) 0.71651(12) 0.0238(3) Uani 1 1 d . . .
N2 N 0.11043(19) 0.68842(17) 0.79662(11) 0.0195(3) Uani 1 1 d . . .
H2A H 0.0558 0.7192 0.8621 0.023 Uiso 1 1 calc R . .
H2B H 0.0429 0.6656 0.7593 0.023 Uiso 1 1 calc R . .
C1 C 0.6012(2) 0.70550(19) 0.75623(13) 0.0168(3) Uani 1 1 d . . .
C2 C 0.4083(2) 0.71027(18) 0.80812(12) 0.0148(3) Uani 1 1 d . . .
C3 C 0.3306(2) 0.76838(19) 0.91859(12) 0.0153(3) Uani 1 1 d . . .
C4 C 0.2706(2) 0.66662(19) 1.01651(13) 0.0177(3) Uani 1 1 d . . .
H4A H 0.2843 0.5565 1.0149 0.021 Uiso 1 1 calc R . .
C5 C 0.1907(2) 0.7264(2) 1.11666(13) 0.0185(3) Uani 1 1 d . . .
H5A H 0.1500 0.6568 1.1833 0.022 Uiso 1 1 calc R . .
C6 C 0.1700(2) 0.8865(2) 1.11977(13) 0.0173(3) Uani 1 1 d . . .
H6A H 0.1138 0.9271 1.1881 0.021 Uiso 1 1 calc R . .
C7 C 0.2317(2) 0.98794(19) 1.02239(13) 0.0153(3) Uani 1 1 d . . .
C8 C 0.3138(2) 0.92890(19) 0.92213(12) 0.0151(3) Uani 1 1 d . . .
H8A H 0.3582 0.9976 0.8562 0.018 Uiso 1 1 calc R . .
C9 C 0.2628(2) 1.2542(2) 0.93398(14) 0.0214(4) Uani 1 1 d . . .
H9A H 0.2348 1.3622 0.9525 0.032 Uiso 1 1 calc R . .
H9B H 0.1919 1.2678 0.8749 0.032 Uiso 1 1 calc R . .
H9C H 0.4025 1.2071 0.9070 0.032 Uiso 1 1 calc R . .
C10 C 0.2969(2) 0.67624(18) 0.75362(12) 0.0149(3) Uani 1 1 d . . .
C11 C 0.3728(2) 0.62853(19) 0.63836(12) 0.0166(3) Uani 1 1 d . . .
H11A H 0.5059 0.6345 0.6111 0.020 Uiso 1 1 calc R . .
H11B H 0.2902 0.7103 0.5850 0.020 Uiso 1 1 calc R . .
C12 C 0.3775(2) 0.45707(19) 0.63682(12) 0.0147(3) Uani 1 1 d . . .
C13 C 0.5414(2) 0.3205(2) 0.65917(12) 0.0170(3) Uani 1 1 d . . .
H13A H 0.6483 0.3349 0.6767 0.020 Uiso 1 1 calc R . .
C14 C 0.5475(2) 0.16417(19) 0.65573(13) 0.0179(3) Uani 1 1 d . . .
H14A H 0.6587 0.0718 0.6718 0.021 Uiso 1 1 calc R . .
C15 C 0.3940(2) 0.13971(19) 0.62925(12) 0.0168(3) Uani 1 1 d . . .
H15A H 0.4007 0.0323 0.6255 0.020 Uiso 1 1 calc R . .
C16 C 0.2301(2) 0.27603(19) 0.60837(12) 0.0160(3) Uani 1 1 d . . .
C17 C 0.2222(2) 0.43366(19) 0.61181(12) 0.0159(3) Uani 1 1 d . . .
H17A H 0.1100 0.5258 0.5970 0.019 Uiso 1 1 calc R . .
C18 C 0.0825(2) 0.1137(2) 0.56148(14) 0.0224(4) Uani 1 1 d . . .
H18A H -0.0415 0.1224 0.5454 0.034 Uiso 1 1 calc R . .
H18B H 0.1134 0.0261 0.6275 0.034 Uiso 1 1 calc R . .
H18C H 0.1853 0.0872 0.4961 0.034 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C7 1.3721(18) . ?
O1 C9 1.4340(19) . ?
O2 C16 1.3717(19) . ?
O2 C18 1.4221(19) . ?
N1 C1 1.157(2) . ?
N2 C10 1.344(2) . ?
N2 H2A 0.8800 . ?
N2 H2B 0.8800 . ?
C1 C2 1.420(2) . ?
C2 C10 1.368(2) . ?
C2 C3 1.500(2) . ?
C3 C4 1.393(2) . ?
C3 C8 1.396(2) . ?
C4 C5 1.391(2) . ?
C4 H4A 0.9500 . ?
C5 C6 1.382(2) . ?
C5 H5A 0.9500 . ?
C6 C7 1.392(2) . ?
C6 H6A 0.9500 . ?
C7 C8 1.390(2) . ?
C8 H8A 0.9500 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 C11 1.516(2) . ?
C11 C12 1.516(2) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C17 1.390(2) . ?
C12 C13 1.398(2) . ?
C13 C14 1.385(2) . ?
C13 H13A 0.9500 . ?
C14 C15 1.390(2) . ?
C14 H14A 0.9500 . ?
C15 C16 1.394(2) . ?
C15 H15A 0.9500 . ?
C16 C17 1.392(2) . ?
C17 H17A 0.9500 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7 O1 C9 117.41(12) . . ?
C16 O2 C18 117.10(12) . . ?
C10 N2 H2A 120.0 . . ?
C10 N2 H2B 120.0 . . ?
H2A N2 H2B 120.0 . . ?
N1 C1 C2 177.54(16) . . ?
C10 C2 C1 120.35(14) . . ?
C10 C2 C3 122.71(13) . . ?
C1 C2 C3 116.72(13) . . ?
C4 C3 C8 119.72(14) . . ?
C4 C3 C2 121.16(14) . . ?
C8 C3 C2 119.09(13) . . ?
C5 C4 C3 119.92(15) . . ?
C5 C4 H4A 120.0 . . ?
C3 C4 H4A 120.0 . . ?
C6 C5 C4 120.44(14) . . ?
C6 C5 H5A 119.8 . . ?
C4 C5 H5A 119.8 . . ?
C5 C6 C7 119.81(14) . . ?
C5 C6 H6A 120.1 . . ?
C7 C6 H6A 120.1 . . ?
O1 C7 C8 123.91(14) . . ?
O1 C7 C6 115.83(13) . . ?
C8 C7 C6 120.25(14) . . ?
C7 C8 C3 119.83(14) . . ?
C7 C8 H8A 120.1 . . ?
C3 C8 H8A 120.1 . . ?
O1 C9 H9A 109.5 . . ?
O1 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
O1 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
N2 C10 C2 122.37(14) . . ?
N2 C10 C11 115.25(13) . . ?
C2 C10 C11 122.34(13) . . ?
C10 C11 C12 114.11(12) . . ?
C10 C11 H11A 108.7 . . ?
C12 C11 H11A 108.7 . . ?
C10 C11 H11B 108.7 . . ?
C12 C11 H11B 108.7 . . ?
H11A C11 H11B 107.6 . . ?
C17 C12 C13 119.32(14) . . ?
C17 C12 C11 120.95(13) . . ?
C13 C12 C11 119.72(14) . . ?
C14 C13 C12 119.79(14) . . ?
C14 C13 H13A 120.1 . . ?
C12 C13 H13A 120.1 . . ?
C13 C14 C15 121.34(14) . . ?
C13 C14 H14A 119.3 . . ?
C15 C14 H14A 119.3 . . ?
C14 C15 C16 118.60(14) . . ?
C14 C15 H15A 120.7 . . ?
C16 C15 H15A 120.7 . . ?
O2 C16 C17 115.55(13) . . ?
O2 C16 C15 123.90(14) . . ?
C17 C16 C15 120.55(14) . . ?
C12 C17 C16 120.38(14) . . ?
C12 C17 H17A 119.8 . . ?
C16 C17 H17A 119.8 . . ?
O2 C18 H18A 109.5 . . ?
O2 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
O2 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 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 C10 159(4) . . . . ?
N1 C1 C2 C3 -16(4) . . . . ?
C10 C2 C3 C4 65.6(2) . . . . ?
C1 C2 C3 C4 -119.86(16) . . . . ?
C10 C2 C3 C8 -112.77(17) . . . . ?
C1 C2 C3 C8 61.82(19) . . . . ?
C8 C3 C4 C5 1.3(2) . . . . ?
C2 C3 C4 C5 -176.99(14) . . . . ?
C3 C4 C5 C6 0.1(2) . . . . ?
C4 C5 C6 C7 -0.8(2) . . . . ?
C9 O1 C7 C8 -0.2(2) . . . . ?
C9 O1 C7 C6 -179.25(13) . . . . ?
C5 C6 C7 O1 179.17(13) . . . . ?
C5 C6 C7 C8 0.1(2) . . . . ?
O1 C7 C8 C3 -177.70(13) . . . . ?
C6 C7 C8 C3 1.3(2) . . . . ?
C4 C3 C8 C7 -2.0(2) . . . . ?
C2 C3 C8 C7 176.34(14) . . . . ?
C1 C2 C10 N2 -176.12(14) . . . . ?
C3 C2 C10 N2 -1.7(2) . . . . ?
C1 C2 C10 C11 1.5(2) . . . . ?
C3 C2 C10 C11 175.85(14) . . . . ?
N2 C10 C11 C12 -64.32(17) . . . . ?
C2 C10 C11 C12 117.94(16) . . . . ?
C10 C11 C12 C17 92.79(16) . . . . ?
C10 C11 C12 C13 -88.17(17) . . . . ?
C17 C12 C13 C14 0.3(2) . . . . ?
C11 C12 C13 C14 -178.80(13) . . . . ?
C12 C13 C14 C15 0.7(2) . . . . ?
C13 C14 C15 C16 -1.4(2) . . . . ?
C18 O2 C16 C17 169.99(13) . . . . ?
C18 O2 C16 C15 -10.2(2) . . . . ?
C14 C15 C16 O2 -178.52(14) . . . . ?
C14 C15 C16 C17 1.3(2) . . . . ?
C13 C12 C17 C16 -0.4(2) . . . . ?
C11 C12 C17 C16 178.66(13) . . . . ?
O2 C16 C17 C12 179.41(13) . . . . ?
C15 C16 C17 C12 -0.4(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        26.50
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.251
_refine_diff_density_min         -0.244
_refine_diff_density_rms         0.048
####################################################################### 
# 
# 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_Compound4a
_database_code_depnum_ccdc_archive 'CCDC 1956322'
loop_
_audit_author_name
_audit_author_address
'Deguang Huang'
;Fujian Institute of Research on the Structure of Matter, CAS
China
;
_audit_update_record             
;
2019-09-27 deposited with the CCDC.	2020-01-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H21 N3'
_chemical_formula_sum            'C15 H21 N3'
_chemical_formula_weight         243.35

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_space_group_name_Hall  '-P 2yn'

loop_
_symmetry_equiv_pos_as_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                   9.8970(3)
_cell_length_b                   9.8470(3)
_cell_length_c                   14.2912(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 93.032(3)
_cell_angle_gamma                90.00
_cell_volume                     1390.81(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2462
_cell_measurement_theta_min      5.3000
_cell_measurement_theta_max      73.7310

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.162
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             528
_exptl_absorpt_coefficient_mu    0.541
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9232
_exptl_absorpt_correction_T_max  0.9735
_exptl_absorpt_process_details   
; 
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018) 
Empirical absorption correction using spherical harmonics, 
 implemented in SCALE3 ABSPACK scaling algorithm. 
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'SuperNova (Mo) X-ray Source'
_diffrn_radiation_monochromator  Mirror
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.5594
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            4954
_diffrn_reflns_av_R_equivalents  0.0187
_diffrn_reflns_av_sigmaI/netI    0.0233
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         5.31
_diffrn_reflns_theta_max         69.98
_reflns_number_total             2605
_reflns_number_gt                2216
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0775P)²+0.4700P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2605
_refine_ls_number_parameters     163
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0559
_refine_ls_R_factor_gt           0.0482
_refine_ls_wR_factor_ref         0.1380
_refine_ls_wR_factor_gt          0.1314
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_restrained_S_all      1.080
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.06674(13) -0.13317(15) 0.06619(10) 0.0312(3) Uani 1 1 d . . .
N2 N 0.24648(12) 0.15768(13) -0.01076(8) 0.0208(3) Uani 1 1 d . . .
H2A H 0.1647 0.1881 -0.0013 0.025 Uiso 1 1 calc R . .
N3 N 0.45208(12) 0.15774(13) 0.07606(9) 0.0212(3) Uani 1 1 d . . .
H3A H 0.5187 0.1024 0.0934 0.025 Uiso 1 1 calc R . .
C1 C 0.16263(14) -0.07174(16) 0.08826(10) 0.0217(3) Uani 1 1 d . . .
C2 C 0.28035(14) 0.00111(15) 0.11879(10) 0.0198(3) Uani 1 1 d . . .
C3 C 0.35226(14) -0.04644(16) 0.20690(10) 0.0206(3) Uani 1 1 d . . .
C4 C 0.37852(15) -0.18492(17) 0.22024(11) 0.0257(4) Uani 1 1 d . . .
H4A H 0.3522 -0.2476 0.1721 0.031 Uiso 1 1 calc R . .
C5 C 0.44225(16) -0.23196(19) 0.30248(12) 0.0322(4) Uani 1 1 d . . .
H5A H 0.4589 -0.3264 0.3104 0.039 Uiso 1 1 calc R . .
C6 C 0.48187(17) -0.1420(2) 0.37333(12) 0.0352(4) Uani 1 1 d . . .
H6A H 0.5262 -0.1743 0.4296 0.042 Uiso 1 1 calc R . .
C7 C 0.45640(17) -0.0046(2) 0.36151(11) 0.0322(4) Uani 1 1 d . . .
H7A H 0.4831 0.0574 0.4099 0.039 Uiso 1 1 calc R . .
C8 C 0.39191(15) 0.04305(17) 0.27911(11) 0.0252(4) Uani 1 1 d . . .
H8A H 0.3746 0.1375 0.2718 0.030 Uiso 1 1 calc R . .
C9 C 0.32456(14) 0.10476(15) 0.06271(10) 0.0187(3) Uani 1 1 d . . .
C10 C 0.29881(14) 0.16390(15) -0.10535(10) 0.0201(3) Uani 1 1 d . . .
H10A H 0.3999 0.1664 -0.0990 0.024 Uiso 1 1 calc R . .
C11 C 0.25633(17) 0.03818(17) -0.16150(12) 0.0283(4) Uani 1 1 d . . .
H11A H 0.2886 -0.0433 -0.1279 0.042 Uiso 1 1 calc R . .
H11B H 0.2956 0.0416 -0.2230 0.042 Uiso 1 1 calc R . .
H11C H 0.1574 0.0353 -0.1698 0.042 Uiso 1 1 calc R . .
C12 C 0.25001(18) 0.29131(17) -0.15600(11) 0.0300(4) Uani 1 1 d . . .
H12A H 0.2781 0.3712 -0.1190 0.045 Uiso 1 1 calc R . .
H12B H 0.1511 0.2894 -0.1643 0.045 Uiso 1 1 calc R . .
H12C H 0.2893 0.2957 -0.2175 0.045 Uiso 1 1 calc R . .
C13 C 0.48356(15) 0.30265(15) 0.06297(10) 0.0214(3) Uani 1 1 d . . .
H13A H 0.4406 0.3325 0.0015 0.026 Uiso 1 1 calc R . .
C14 C 0.42795(18) 0.39020(18) 0.13952(13) 0.0346(4) Uani 1 1 d . . .
H14A H 0.3298 0.3778 0.1402 0.052 Uiso 1 1 calc R . .
H14B H 0.4482 0.4858 0.1274 0.052 Uiso 1 1 calc R . .
H14C H 0.4700 0.3635 0.2004 0.052 Uiso 1 1 calc R . .
C15 C 0.63596(16) 0.31795(17) 0.05875(13) 0.0293(4) Uani 1 1 d . . .
H15A H 0.6682 0.2602 0.0087 0.044 Uiso 1 1 calc R . .
H15B H 0.6799 0.2906 0.1189 0.044 Uiso 1 1 calc R . .
H15C H 0.6580 0.4129 0.0459 0.044 Uiso 1 1 calc R . .


_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 1.155(2) . ?
N2 C9 1.3730(18) . ?
N2 C10 1.4743(18) . ?
N2 H2A 0.8800 . ?
N3 C9 1.3697(19) . ?
N3 C13 1.4745(19) . ?
N3 H3A 0.8800 . ?
C1 C2 1.417(2) . ?
C2 C9 1.383(2) . ?
C2 C3 1.489(2) . ?
C3 C8 1.397(2) . ?
C3 C4 1.399(2) . ?
C4 C5 1.384(2) . ?
C4 H4A 0.9500 . ?
C5 C6 1.386(3) . ?
C5 H5A 0.9500 . ?
C6 C7 1.385(3) . ?
C6 H6A 0.9500 . ?
C7 C8 1.391(2) . ?
C7 H7A 0.9500 . ?
C8 H8A 0.9500 . ?
C10 C12 1.515(2) . ?
C10 C11 1.522(2) . ?
C10 H10A 1.0000 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 C14 1.519(2) . ?
C13 C15 1.520(2) . ?
C13 H13A 1.0000 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
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
C9 N2 C10 120.41(11) . . ?
C9 N2 H2A 119.8 . . ?
C10 N2 H2A 119.8 . . ?
C9 N3 C13 123.38(12) . . ?
C9 N3 H3A 118.3 . . ?
C13 N3 H3A 118.3 . . ?
N1 C1 C2 177.77(16) . . ?
C9 C2 C1 118.37(13) . . ?
C9 C2 C3 124.79(13) . . ?
C1 C2 C3 116.72(13) . . ?
C8 C3 C4 118.10(14) . . ?
C8 C3 C2 121.96(14) . . ?
C4 C3 C2 119.91(14) . . ?
C5 C4 C3 120.99(16) . . ?
C5 C4 H4A 119.5 . . ?
C3 C4 H4A 119.5 . . ?
C4 C5 C6 120.33(16) . . ?
C4 C5 H5A 119.8 . . ?
C6 C5 H5A 119.8 . . ?
C7 C6 C5 119.51(15) . . ?
C7 C6 H6A 120.2 . . ?
C5 C6 H6A 120.2 . . ?
C6 C7 C8 120.35(17) . . ?
C6 C7 H7A 119.8 . . ?
C8 C7 H7A 119.8 . . ?
C7 C8 C3 120.72(16) . . ?
C7 C8 H8A 119.6 . . ?
C3 C8 H8A 119.6 . . ?
N3 C9 N2 116.05(13) . . ?
N3 C9 C2 121.18(13) . . ?
N2 C9 C2 122.74(13) . . ?
N2 C10 C12 110.73(12) . . ?
N2 C10 C11 110.42(12) . . ?
C12 C10 C11 110.46(13) . . ?
N2 C10 H10A 108.4 . . ?
C12 C10 H10A 108.4 . . ?
C11 C10 H10A 108.4 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C10 C12 H12A 109.5 . . ?
C10 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C10 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N3 C13 C14 111.77(13) . . ?
N3 C13 C15 108.53(12) . . ?
C14 C13 C15 111.74(13) . . ?
N3 C13 H13A 108.2 . . ?
C14 C13 H13A 108.2 . . ?
C15 C13 H13A 108.2 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C13 C15 H15C 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 C9 -171(4) . . . . ?
N1 C1 C2 C3 12(4) . . . . ?
C9 C2 C3 C8 52.5(2) . . . . ?
C1 C2 C3 C8 -131.56(15) . . . . ?
C9 C2 C3 C4 -129.36(16) . . . . ?
C1 C2 C3 C4 46.62(19) . . . . ?
C8 C3 C4 C5 -0.2(2) . . . . ?
C2 C3 C4 C5 -178.41(13) . . . . ?
C3 C4 C5 C6 -0.3(2) . . . . ?
C4 C5 C6 C7 0.4(2) . . . . ?
C5 C6 C7 C8 -0.2(2) . . . . ?
C6 C7 C8 C3 -0.2(2) . . . . ?
C4 C3 C8 C7 0.4(2) . . . . ?
C2 C3 C8 C7 178.62(14) . . . . ?
C13 N3 C9 N2 37.9(2) . . . . ?
C13 N3 C9 C2 -144.05(14) . . . . ?
C10 N2 C9 N3 52.09(19) . . . . ?
C10 N2 C9 C2 -125.91(15) . . . . ?
C1 C2 C9 N3 -164.71(13) . . . . ?
C3 C2 C9 N3 11.2(2) . . . . ?
C1 C2 C9 N2 13.2(2) . . . . ?
C3 C2 C9 N2 -170.88(13) . . . . ?
C9 N2 C10 C12 -144.05(14) . . . . ?
C9 N2 C10 C11 93.29(16) . . . . ?
C9 N3 C13 C14 70.89(18) . . . . ?
C9 N3 C13 C15 -165.43(13) . . . . ?

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        69.98
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         0.597
_refine_diff_density_min         -0.574
_refine_diff_density_rms         0.053
####################################################################### 
# 
# 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_Compound6a
_database_code_depnum_ccdc_archive 'CCDC 1956324'
loop_
_audit_author_name
_audit_author_address
'Deguang Huang'
;Fujian Institute of Research on the Structure of Matter, CAS
China
;
_audit_update_record             
;
2019-09-27 deposited with the CCDC.	2020-01-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H16 N4 S3'
_chemical_formula_sum            'C19 H16 N4 S3'
_chemical_formula_weight         396.54

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   Pbcn
_symmetry_space_group_name_Hall  '-P 2n 2ab'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y+1/2, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y, -z+1/2'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y, z-1/2'

_cell_length_a                   10.5993(3)
_cell_length_b                   11.9893(4)
_cell_length_c                   28.8362(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     3664.45(19)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    3928
_cell_measurement_theta_min      5.1540
_cell_measurement_theta_max      72.3310

_exptl_crystal_description       column
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.438
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1648
_exptl_absorpt_coefficient_mu    3.781
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4516
_exptl_absorpt_correction_T_max  0.7036
_exptl_absorpt_process_details   
; 
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018) 
Empirical absorption correction using spherical harmonics, 
 implemented in SCALE3 ABSPACK scaling algorithm. 
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'SuperNova (Cu) X-ray Source'
_diffrn_radiation_monochromator  Mirror
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.5594
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            9121
_diffrn_reflns_av_R_equivalents  0.0256
_diffrn_reflns_av_sigmaI/netI    0.0261
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_theta_min         5.18
_diffrn_reflns_theta_max         70.00
_reflns_number_total             3458
_reflns_number_gt                3046
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0425P)²+2.7109P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3458
_refine_ls_number_parameters     272
_refine_ls_number_restraints     144
_refine_ls_R_factor_all          0.0410
_refine_ls_R_factor_gt           0.0349
_refine_ls_wR_factor_ref         0.0911
_refine_ls_wR_factor_gt          0.0879
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_restrained_S_all      1.072
_refine_ls_shift/su_max          0.001
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.69876(5) 0.85894(4) 0.304072(16) 0.02187(13) Uani 1 1 d . . .
S3 S 0.73203(5) 0.37828(4) 0.535688(16) 0.02132(13) Uani 1 1 d . . .
N1 N 0.63118(15) 0.46719(13) 0.45018(5) 0.0178(3) Uani 1 1 d . . .
N2 N 0.49583(15) 0.51901(13) 0.38735(5) 0.0165(3) Uani 1 1 d . A .
N3 N 0.56048(15) 0.66205(13) 0.33510(5) 0.0173(3) Uani 1 1 d . A .
N4 N 0.43890(16) 0.36644(14) 0.45049(6) 0.0220(4) Uani 1 1 d . . .
H4A H 0.4110 0.3976 0.4248 0.026 Uiso 1 1 calc R . .
H4B H 0.3925 0.3165 0.4650 0.026 Uiso 1 1 calc R . .
C1 C 0.60433(18) 0.53038(15) 0.41115(6) 0.0158(4) Uani 1 1 d . . .
C2 C 0.69745(18) 0.60929(16) 0.39808(6) 0.0174(4) Uani 1 1 d . . .
C3 C 0.81271(19) 0.62425(17) 0.42802(7) 0.0218(4) Uani 1 1 d . . .
H3B H 0.7864 0.6252 0.4610 0.026 Uiso 1 1 calc R . .
H3A H 0.8513 0.6975 0.4209 0.026 Uiso 1 1 calc R . .
C4 C 0.9121(2) 0.53327(19) 0.42138(8) 0.0299(5) Uani 1 1 d . . .
H4C H 0.9842 0.5481 0.4417 0.045 Uiso 1 1 calc R . .
H4D H 0.9401 0.5327 0.3890 0.045 Uiso 1 1 calc R . .
H4E H 0.8755 0.4606 0.4292 0.045 Uiso 1 1 calc R . .
C5 C 0.67187(18) 0.67092(15) 0.35812(6) 0.0164(4) Uani 1 1 d . . .
C6 C 0.75970(19) 0.75135(16) 0.33718(6) 0.0178(4) Uani 1 1 d . . .
C7 C 0.8897(2) 0.75201(17) 0.33563(6) 0.0212(4) Uani 1 1 d . . .
H7A H 0.9412 0.6995 0.3514 0.025 Uiso 1 1 calc R . .
C8 C 0.9380(2) 0.83974(17) 0.30789(6) 0.0232(4) Uani 1 1 d . . .
H8A H 1.0255 0.8518 0.3028 0.028 Uiso 1 1 calc R . .
C9 C 0.8463(2) 0.90456(17) 0.28937(7) 0.0244(5) Uani 1 1 d . . .
H9A H 0.8620 0.9679 0.2704 0.029 Uiso 1 1 calc R . .
C10 C 0.47850(18) 0.58768(15) 0.35113(6) 0.0169(4) Uani 1 1 d . . .
S2 S 0.24828(7) 0.47951(6) 0.34108(3) 0.0205(2) Uani 0.782(2) 1 d PDU A 1
C11 C 0.35786(14) 0.57857(12) 0.32699(6) 0.0181(3) Uani 0.782(2) 1 d PDU A 1
C12 C 0.3122(3) 0.6472(3) 0.29279(12) 0.0194(4) Uani 0.782(2) 1 d PDU A 1
H12A H 0.3601 0.7071 0.2804 0.023 Uiso 0.782(2) 1 calc PR A 1
C13 C 0.1872(3) 0.6221(3) 0.27710(17) 0.0228(5) Uani 0.782(2) 1 d PDU A 1
H13A H 0.1420 0.6616 0.2539 0.027 Uiso 0.782(2) 1 calc PR A 1
C14 C 0.1439(3) 0.5317(3) 0.30132(13) 0.0224(5) Uani 0.782(2) 1 d PDU A 1
H14A H 0.0626 0.5004 0.2965 0.027 Uiso 0.782(2) 1 calc PR A 1
S2' S 0.3225(3) 0.6756(2) 0.28582(11) 0.0219(5) Uani 0.218(2) 1 d PDU A 2
C11' C 0.35786(14) 0.57857(12) 0.32699(6) 0.0181(3) Uani 0.218(2) 1 d PDU A 2
C12' C 0.2607(8) 0.5051(9) 0.3340(5) 0.0201(6) Uani 0.218(2) 1 d PDU A 2
H12B H 0.2676 0.4490 0.3571 0.024 Uiso 0.218(2) 1 calc PR A 2
C13' C 0.1489(12) 0.5128(12) 0.3064(5) 0.0220(6) Uani 0.218(2) 1 d PDU A 2
H13B H 0.0747 0.4684 0.3058 0.026 Uiso 0.218(2) 1 calc PR A 2
C14' C 0.1829(10) 0.6048(13) 0.2812(7) 0.0221(6) Uani 0.218(2) 1 d PDU A 2
H14B H 0.1237 0.6317 0.2591 0.026 Uiso 0.218(2) 1 calc PR A 2
C15 C 0.55172(18) 0.39493(15) 0.46748(6) 0.0167(4) Uani 1 1 d . . .
C16 C 0.59276(18) 0.33767(15) 0.50989(6) 0.0174(4) Uani 1 1 d . . .
C17 C 0.53490(19) 0.25195(16) 0.53417(6) 0.0194(4) Uani 1 1 d . . .
H17A H 0.4576 0.2179 0.5253 0.023 Uiso 1 1 calc R . .
C18 C 0.6062(2) 0.22142(17) 0.57417(7) 0.0246(4) Uani 1 1 d . . .
H18A H 0.5814 0.1644 0.5952 0.030 Uiso 1 1 calc R . .
C19 C 0.7130(2) 0.28223(17) 0.57910(7) 0.0232(4) Uani 1 1 d . . .
H19B H 0.7710 0.2727 0.6039 0.028 Uiso 1 1 calc R . .


_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
S1 C9 1.710(2) . ?
S1 C6 1.730(2) . ?
S3 C19 1.713(2) . ?
S3 C16 1.723(2) . ?
N1 C15 1.307(2) . ?
N1 C1 1.386(2) . ?
N2 C10 1.342(2) . ?
N2 C1 1.346(2) . ?
N3 C10 1.328(2) . ?
N3 C5 1.359(2) . ?
N4 C15 1.337(3) . ?
N4 H4A 0.8800 . ?
N4 H4B 0.8800 . ?
C1 C2 1.418(3) . ?
C2 C5 1.395(3) . ?
C2 C3 1.507(3) . ?
C3 C4 1.528(3) . ?
C3 H3B 0.9900 . ?
C3 H3A 0.9900 . ?
C4 H4C 0.9800 . ?
C4 H4D 0.9800 . ?
C4 H4E 0.9800 . ?
C5 C6 1.470(3) . ?
C6 C7 1.379(3) . ?
C7 C8 1.417(3) . ?
C7 H7A 0.9500 . ?
C8 C9 1.355(3) . ?
C8 H8A 0.9500 . ?
C9 H9A 0.9500 . ?
C10 C11 1.460(2) . ?
S2 C11 1.7102(9) . ?
S2 C14 1.7114(10) . ?
C11 C12 1.3724(10) . ?
C12 C13 1.4317(10) . ?
C12 H12A 0.9500 . ?
C13 C14 1.3694(10) . ?
C13 H13A 0.9500 . ?
C14 H14A 0.9500 . ?
S2' C14' 1.7107(11) . ?
C12' C13' 1.4301(11) . ?
C12' H12B 0.9500 . ?
C13' C14' 1.3699(11) . ?
C13' H13B 0.9500 . ?
C14' H14B 0.9500 . ?
C15 C16 1.468(3) . ?
C16 C17 1.387(3) . ?
C17 C18 1.427(3) . ?
C17 H17A 0.9500 . ?
C18 C19 1.354(3) . ?
C18 H18A 0.9500 . ?
C19 H19B 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
C9 S1 C6 91.95(10) . . ?
C19 S3 C16 91.40(10) . . ?
C15 N1 C1 122.67(16) . . ?
C10 N2 C1 116.84(16) . . ?
C10 N3 C5 116.81(16) . . ?
C15 N4 H4A 120.0 . . ?
C15 N4 H4B 120.0 . . ?
H4A N4 H4B 120.0 . . ?
N2 C1 N1 122.28(17) . . ?
N2 C1 C2 121.77(16) . . ?
N1 C1 C2 115.94(16) . . ?
C5 C2 C1 115.94(17) . . ?
C5 C2 C3 124.59(17) . . ?
C1 C2 C3 119.43(17) . . ?
C2 C3 C4 113.70(17) . . ?
C2 C3 H3B 108.8 . . ?
C4 C3 H3B 108.8 . . ?
C2 C3 H3A 108.8 . . ?
C4 C3 H3A 108.8 . . ?
H3B C3 H3A 107.7 . . ?
C3 C4 H4C 109.5 . . ?
C3 C4 H4D 109.5 . . ?
H4C C4 H4D 109.5 . . ?
C3 C4 H4E 109.5 . . ?
H4C C4 H4E 109.5 . . ?
H4D C4 H4E 109.5 . . ?
N3 C5 C2 122.06(17) . . ?
N3 C5 C6 113.64(16) . . ?
C2 C5 C6 124.30(17) . . ?
C7 C6 C5 130.54(19) . . ?
C7 C6 S1 110.55(15) . . ?
C5 C6 S1 118.64(15) . . ?
C6 C7 C8 112.57(19) . . ?
C6 C7 H7A 123.7 . . ?
C8 C7 H7A 123.7 . . ?
C9 C8 C7 112.87(19) . . ?
C9 C8 H8A 123.6 . . ?
C7 C8 H8A 123.6 . . ?
C8 C9 S1 112.04(15) . . ?
C8 C9 H9A 124.0 . . ?
S1 C9 H9A 124.0 . . ?
N3 C10 N2 126.37(18) . . ?
N3 C10 C11 117.21(15) . . ?
N2 C10 C11 116.42(16) . . ?
C11 S2 C14 91.50(12) . . ?
C12 C11 C10 127.35(15) . . ?
C12 C11 S2 110.33(15) . . ?
C10 C11 S2 122.24(12) . . ?
C11 C12 C13 115.3(3) . . ?
C11 C12 H12A 122.3 . . ?
C13 C12 H12A 122.3 . . ?
C14 C13 C12 108.4(3) . . ?
C14 C13 H13A 125.8 . . ?
C12 C13 H13A 125.8 . . ?
C13 C14 S2 114.5(2) . . ?
C13 C14 H14A 122.8 . . ?
S2 C14 H14A 122.8 . . ?
C13' C12' H12B 120.0 . . ?
C14' C13' C12' 97.4(12) . . ?
C14' C13' H13B 131.3 . . ?
C12' C13' H13B 131.3 . . ?
C13' C14' S2' 125.8(11) . . ?
C13' C14' H14B 117.1 . . ?
S2' C14' H14B 117.1 . . ?
N1 C15 N4 127.30(17) . . ?
N1 C15 C16 115.90(17) . . ?
N4 C15 C16 116.80(17) . . ?
C17 C16 C15 129.49(18) . . ?
C17 C16 S3 111.74(14) . . ?
C15 C16 S3 118.77(14) . . ?
C16 C17 C18 111.34(19) . . ?
C16 C17 H17A 124.3 . . ?
C18 C17 H17A 124.3 . . ?
C19 C18 C17 112.92(19) . . ?
C19 C18 H18A 123.5 . . ?
C17 C18 H18A 123.5 . . ?
C18 C19 S3 112.59(15) . . ?
C18 C19 H19B 123.7 . . ?
S3 C19 H19B 123.7 . . ?

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
C10 N2 C1 N1 177.64(16) . . . . ?
C10 N2 C1 C2 -1.4(3) . . . . ?
C15 N1 C1 N2 -2.3(3) . . . . ?
C15 N1 C1 C2 176.81(17) . . . . ?
N2 C1 C2 C5 -2.5(3) . . . . ?
N1 C1 C2 C5 178.44(16) . . . . ?
N2 C1 C2 C3 175.52(17) . . . . ?
N1 C1 C2 C3 -3.6(3) . . . . ?
C5 C2 C3 C4 -103.8(2) . . . . ?
C1 C2 C3 C4 78.4(2) . . . . ?
C10 N3 C5 C2 -3.1(3) . . . . ?
C10 N3 C5 C6 177.50(16) . . . . ?
C1 C2 C5 N3 4.8(3) . . . . ?
C3 C2 C5 N3 -173.05(17) . . . . ?
C1 C2 C5 C6 -175.87(17) . . . . ?
C3 C2 C5 C6 6.3(3) . . . . ?
N3 C5 C6 C7 -148.3(2) . . . . ?
C2 C5 C6 C7 32.3(3) . . . . ?
N3 C5 C6 S1 25.1(2) . . . . ?
C2 C5 C6 S1 -154.25(16) . . . . ?
C9 S1 C6 C7 -0.87(15) . . . . ?
C9 S1 C6 C5 -175.56(15) . . . . ?
C5 C6 C7 C8 174.14(18) . . . . ?
S1 C6 C7 C8 0.3(2) . . . . ?
C6 C7 C8 C9 0.7(2) . . . . ?
C7 C8 C9 S1 -1.4(2) . . . . ?
C6 S1 C9 C8 1.28(16) . . . . ?
C5 N3 C10 N2 -1.3(3) . . . . ?
C5 N3 C10 C11 179.21(16) . . . . ?
C1 N2 C10 N3 3.5(3) . . . . ?
C1 N2 C10 C11 -176.99(15) . . . . ?
N3 C10 C11 C12 -8.5(4) . . . . ?
N2 C10 C11 C12 171.9(3) . . . . ?
N3 C10 C11 S2 175.03(14) . . . . ?
N2 C10 C11 S2 -4.5(2) . . . . ?
C14 S2 C11 C12 -0.2(3) . . . . ?
C14 S2 C11 C10 176.9(2) . . . . ?
C10 C11 C12 C13 -176.6(4) . . . . ?
S2 C11 C12 C13 0.3(5) . . . . ?
C11 C12 C13 C14 -0.3(7) . . . . ?
C12 C13 C14 S2 0.1(6) . . . . ?
C11 S2 C14 C13 0.0(4) . . . . ?
C12' C13' C14' S2' 1(2) . . . . ?
C1 N1 C15 N4 3.2(3) . . . . ?
C1 N1 C15 C16 -177.89(16) . . . . ?
N1 C15 C16 C17 -174.61(18) . . . . ?
N4 C15 C16 C17 4.4(3) . . . . ?
N1 C15 C16 S3 5.7(2) . . . . ?
N4 C15 C16 S3 -175.32(14) . . . . ?
C19 S3 C16 C17 -0.51(15) . . . . ?
C19 S3 C16 C15 179.24(15) . . . . ?
C15 C16 C17 C18 -179.22(18) . . . . ?
S3 C16 C17 C18 0.5(2) . . . . ?
C16 C17 C18 C19 -0.2(2) . . . . ?
C17 C18 C19 S3 -0.2(2) . . . . ?
C16 S3 C19 C18 0.39(16) . . . . ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        70.00
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.493
_refine_diff_density_min         -0.470
_refine_diff_density_rms         0.058
####################################################################### 
# 
# 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_full
_database_code_depnum_ccdc_archive 'CCDC 1969352'
loop_
_audit_author_name
_audit_author_address
'Deguang Huang'
;Fujian Institute of Research on the Structure of Matter, CAS
China
;
_audit_update_record             
;
2019-12-02 deposited with the CCDC.	2020-01-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H12 N4'
_chemical_formula_sum            'C14 H12 N4'
_chemical_formula_weight         236.28

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1
_symmetry_space_group_name_Hall  '-P 1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   4.4117(4)
_cell_length_b                   11.8292(13)
_cell_length_c                   12.0532(11)
_cell_angle_alpha                97.480(8)
_cell_angle_beta                 97.624(7)
_cell_angle_gamma                93.401(8)
_cell_volume                     616.27(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    1145
_cell_measurement_theta_min      3.7080
_cell_measurement_theta_max      73.0980

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.273
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             248
_exptl_absorpt_coefficient_mu    0.636
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9107
_exptl_absorpt_correction_T_max  0.9750
_exptl_absorpt_process_details   
; 
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018) 
Empirical absorption correction using spherical harmonics, 
 implemented in SCALE3 ABSPACK scaling algorithm. 
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.5594
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            3598
_diffrn_reflns_av_R_equivalents  0.0253
_diffrn_reflns_av_sigmaI/netI    0.0353
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       3
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.74
_diffrn_reflns_theta_max         69.99
_reflns_number_total             2316
_reflns_number_gt                1725
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0374P)²+0.4161P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2316
_refine_ls_number_parameters     163
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0783
_refine_ls_R_factor_gt           0.0584
_refine_ls_wR_factor_ref         0.1896
_refine_ls_wR_factor_gt          0.1834
_refine_ls_goodness_of_fit_ref   1.300
_refine_ls_restrained_S_all      1.300
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.8122(10) 0.7294(3) 0.5374(3) 0.0890(11) Uani 1 1 d . . .
N2 N 0.4441(6) 0.6315(2) 0.8698(2) 0.0577(7) Uani 1 1 d . . .
N3 N 0.8290(7) 0.8183(2) 0.9321(2) 0.0599(7) Uani 1 1 d . . .
H3A H 0.7043 0.7677 0.9543 0.072 Uiso 1 1 calc R . .
H3B H 0.9302 0.8734 0.9817 0.072 Uiso 1 1 calc R . .
N4 N 0.8201(6) 1.0745(2) 0.8466(2) 0.0557(7) Uani 1 1 d . . .
C1 C 0.7686(8) 0.7291(3) 0.6290(3) 0.0607(9) Uani 1 1 d . . .
C2 C 0.7116(7) 0.7272(3) 0.7425(2) 0.0490(7) Uani 1 1 d . . .
C3 C 0.4984(7) 0.6347(3) 0.7623(3) 0.0501(7) Uani 1 1 d . . .
C4 C 0.3569(8) 0.5508(3) 0.6748(3) 0.0649(9) Uani 1 1 d . . .
H4A H 0.3952 0.5534 0.5995 0.078 Uiso 1 1 calc R . .
C5 C 0.1624(9) 0.4647(3) 0.6985(4) 0.0771(11) Uani 1 1 d . . .
H5A H 0.0659 0.4075 0.6396 0.093 Uiso 1 1 calc R . .
C6 C 0.1087(10) 0.4621(3) 0.8077(4) 0.0803(12) Uani 1 1 d . . .
H6A H -0.0242 0.4034 0.8261 0.096 Uiso 1 1 calc R . .
C7 C 0.2522(9) 0.5465(3) 0.8889(4) 0.0714(10) Uani 1 1 d . . .
H7A H 0.2133 0.5449 0.9643 0.086 Uiso 1 1 calc R . .
C8 C 0.8644(7) 0.8116(3) 0.8237(2) 0.0480(7) Uani 1 1 d . . .
C9 C 1.0778(7) 0.9044(3) 0.7944(3) 0.0556(8) Uani 1 1 d . . .
H9A H 1.1817 0.8728 0.7306 0.067 Uiso 1 1 calc R . .
H9B H 1.2371 0.9306 0.8601 0.067 Uiso 1 1 calc R . .
C10 C 0.9065(7) 1.0050(3) 0.7623(2) 0.0477(7) Uani 1 1 d . . .
C11 C 0.8402(9) 1.0233(3) 0.6507(3) 0.0647(9) Uani 1 1 d . . .
H11A H 0.9039 0.9724 0.5921 0.078 Uiso 1 1 calc R . .
C12 C 0.6817(10) 1.1156(3) 0.6251(3) 0.0748(11) Uani 1 1 d . . .
H12A H 0.6372 1.1296 0.5490 0.090 Uiso 1 1 calc R . .
C13 C 0.5895(9) 1.1865(3) 0.7107(4) 0.0710(10) Uani 1 1 d . . .
H13A H 0.4777 1.2503 0.6956 0.085 Uiso 1 1 calc R . .
C14 C 0.6629(9) 1.1631(3) 0.8192(3) 0.0678(9) Uani 1 1 d . . .
H14A H 0.5986 1.2127 0.8787 0.081 Uiso 1 1 calc R . .


_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 1.146(4) . ?
N2 C7 1.339(5) . ?
N2 C3 1.353(4) . ?
N3 C8 1.330(4) . ?
N3 H3A 0.8800 . ?
N3 H3B 0.8800 . ?
N4 C10 1.333(4) . ?
N4 C14 1.344(4) . ?
C1 C2 1.426(4) . ?
C2 C8 1.378(4) . ?
C2 C3 1.464(5) . ?
C3 C4 1.402(5) . ?
C4 C5 1.375(6) . ?
C4 H4A 0.9500 . ?
C5 C6 1.372(6) . ?
C5 H5A 0.9500 . ?
C6 C7 1.365(6) . ?
C6 H6A 0.9500 . ?
C7 H7A 0.9500 . ?
C8 C9 1.510(4) . ?
C9 C10 1.512(4) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.385(4) . ?
C11 C12 1.377(5) . ?
C11 H11A 0.9500 . ?
C12 C13 1.364(6) . ?
C12 H12A 0.9500 . ?
C13 C14 1.374(5) . ?
C13 H13A 0.9500 . ?
C14 H14A 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
C7 N2 C3 117.9(3) . . ?
C8 N3 H3A 120.0 . . ?
C8 N3 H3B 120.0 . . ?
H3A N3 H3B 120.0 . . ?
C10 N4 C14 117.3(3) . . ?
N1 C1 C2 179.1(5) . . ?
C8 C2 C1 117.1(3) . . ?
C8 C2 C3 126.0(3) . . ?
C1 C2 C3 116.9(3) . . ?
N2 C3 C4 120.3(3) . . ?
N2 C3 C2 117.4(3) . . ?
C4 C3 C2 122.2(3) . . ?
C5 C4 C3 119.8(4) . . ?
C5 C4 H4A 120.1 . . ?
C3 C4 H4A 120.1 . . ?
C6 C5 C4 119.5(4) . . ?
C6 C5 H5A 120.3 . . ?
C4 C5 H5A 120.3 . . ?
C7 C6 C5 117.9(4) . . ?
C7 C6 H6A 121.1 . . ?
C5 C6 H6A 121.1 . . ?
N2 C7 C6 124.6(4) . . ?
N2 C7 H7A 117.7 . . ?
C6 C7 H7A 117.7 . . ?
N3 C8 C2 122.4(3) . . ?
N3 C8 C9 115.6(3) . . ?
C2 C8 C9 121.9(3) . . ?
C8 C9 C10 111.5(2) . . ?
C8 C9 H9A 109.3 . . ?
C10 C9 H9A 109.3 . . ?
C8 C9 H9B 109.3 . . ?
C10 C9 H9B 109.3 . . ?
H9A C9 H9B 108.0 . . ?
N4 C10 C11 121.7(3) . . ?
N4 C10 C9 116.6(3) . . ?
C11 C10 C9 121.6(3) . . ?
C12 C11 C10 119.8(3) . . ?
C12 C11 H11A 120.1 . . ?
C10 C11 H11A 120.1 . . ?
C13 C12 C11 118.9(3) . . ?
C13 C12 H12A 120.5 . . ?
C11 C12 H12A 120.5 . . ?
C12 C13 C14 118.2(3) . . ?
C12 C13 H13A 120.9 . . ?
C14 C13 H13A 120.9 . . ?
N4 C14 C13 124.1(4) . . ?
N4 C14 H14A 118.0 . . ?
C13 C14 H14A 118.0 . . ?

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
N1 C1 C2 C8 172(100) . . . . ?
N1 C1 C2 C3 -7(27) . . . . ?
C7 N2 C3 C4 -0.1(5) . . . . ?
C7 N2 C3 C2 -179.2(3) . . . . ?
C8 C2 C3 N2 0.3(4) . . . . ?
C1 C2 C3 N2 179.6(3) . . . . ?
C8 C2 C3 C4 -178.8(3) . . . . ?
C1 C2 C3 C4 0.5(4) . . . . ?
N2 C3 C4 C5 -0.1(5) . . . . ?
C2 C3 C4 C5 178.9(3) . . . . ?
C3 C4 C5 C6 0.1(6) . . . . ?
C4 C5 C6 C7 0.2(6) . . . . ?
C3 N2 C7 C6 0.5(6) . . . . ?
C5 C6 C7 N2 -0.5(6) . . . . ?
C1 C2 C8 N3 179.9(3) . . . . ?
C3 C2 C8 N3 -0.8(5) . . . . ?
C1 C2 C8 C9 1.4(4) . . . . ?
C3 C2 C8 C9 -179.3(3) . . . . ?
N3 C8 C9 C10 -91.2(3) . . . . ?
C2 C8 C9 C10 87.4(4) . . . . ?
C14 N4 C10 C11 0.5(5) . . . . ?
C14 N4 C10 C9 -178.9(3) . . . . ?
C8 C9 C10 N4 75.5(4) . . . . ?
C8 C9 C10 C11 -103.9(4) . . . . ?
N4 C10 C11 C12 0.2(5) . . . . ?
C9 C10 C11 C12 179.5(3) . . . . ?
C10 C11 C12 C13 -0.8(6) . . . . ?
C11 C12 C13 C14 0.8(6) . . . . ?
C10 N4 C14 C13 -0.6(5) . . . . ?
C12 C13 C14 N4 -0.1(6) . . . . ?

_diffrn_measured_fraction_theta_max 0.986
_diffrn_reflns_theta_full        69.99
_diffrn_measured_fraction_theta_full 0.986
_refine_diff_density_max         0.172
_refine_diff_density_min         -0.236
_refine_diff_density_rms         0.040
####################################################################### 
# 
# 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_Compound6b
_database_code_depnum_ccdc_archive 'CCDC 1956325'
loop_
_audit_author_name
_audit_author_address
'Deguang Huang'
;Fujian Institute of Research on the Structure of Matter, CAS
China
;
_audit_update_record             
;
2019-09-27 deposited with the CCDC.	2020-01-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C25 H22 N4'
_chemical_formula_sum            'C25 H22 N4'
_chemical_formula_weight         378.47

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   'P n 21 a'
_symmetry_space_group_name_Hall  'P -2ac -2n'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x+1/2, y, -z+1/2'
'-x+1/2, y+1/2, z+1/2'
'-x, y+1/2, -z'

_cell_length_a                   11.7806(4)
_cell_length_b                   14.4288(4)
_cell_length_c                   11.4659(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1948.97(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2523
_cell_measurement_theta_min      4.9030
_cell_measurement_theta_max      72.4350

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.290
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             800
_exptl_absorpt_coefficient_mu    0.606
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8390
_exptl_absorpt_correction_T_max  0.9419
_exptl_absorpt_process_details   
; 
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018) 
Empirical absorption correction using spherical harmonics, 
 implemented in SCALE3 ABSPACK scaling algorithm. 
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'SuperNova (Cu) X-ray Source'
_diffrn_radiation_monochromator  Mirror
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.5594
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            4784
_diffrn_reflns_av_R_equivalents  0.0240
_diffrn_reflns_av_sigmaI/netI    0.0314
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         4.93
_diffrn_reflns_theta_max         69.98
_reflns_number_total             2552
_reflns_number_gt                2413
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0412P)²+0.0932P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.1(4)
_refine_ls_number_reflns         2552
_refine_ls_number_parameters     262
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0335
_refine_ls_R_factor_gt           0.0308
_refine_ls_wR_factor_ref         0.0754
_refine_ls_wR_factor_gt          0.0741
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_restrained_S_all      1.077
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.32886(12) 0.24673(11) 0.84381(13) 0.0157(3) Uani 1 1 d . . .
N2 N 0.47633(12) 0.29319(11) 0.97382(12) 0.0149(3) Uani 1 1 d . . .
N3 N 0.60344(12) 0.41470(11) 0.92039(13) 0.0159(3) Uani 1 1 d . . .
N4 N 0.35092(13) 0.13733(11) 0.99639(13) 0.0188(3) Uani 1 1 d . . .
H4A H 0.4143 0.1624 1.0219 0.023 Uiso 1 1 calc R . .
H4B H 0.3228 0.0881 1.0314 0.023 Uiso 1 1 calc R . .
C1 C 0.42379(15) 0.29904(13) 0.86920(15) 0.0153(4) Uani 1 1 d . . .
C2 C 0.46149(15) 0.36234(12) 0.78318(15) 0.0152(4) Uani 1 1 d . . .
C3 C 0.40592(15) 0.36785(13) 0.66542(15) 0.0178(4) Uani 1 1 d . . .
H3B H 0.4208 0.4297 0.6312 0.021 Uiso 1 1 calc R . .
H3C H 0.3228 0.3612 0.6749 0.021 Uiso 1 1 calc R . .
C4 C 0.44835(18) 0.29364(16) 0.58191(16) 0.0274(4) Uani 1 1 d . . .
H4C H 0.4097 0.3002 0.5067 0.041 Uiso 1 1 calc R . .
H4D H 0.4323 0.2322 0.6145 0.041 Uiso 1 1 calc R . .
H4E H 0.5304 0.3007 0.5708 0.041 Uiso 1 1 calc R . .
C5 C 0.55391(15) 0.41693(12) 0.81319(15) 0.0150(4) Uani 1 1 d . . .
C6 C 0.60842(15) 0.48297(13) 0.72960(16) 0.0159(4) Uani 1 1 d . . .
C7 C 0.69080(15) 0.45093(14) 0.65238(16) 0.0200(4) Uani 1 1 d . . .
H7A H 0.7067 0.3865 0.6481 0.024 Uiso 1 1 calc R . .
C8 C 0.75014(16) 0.51235(15) 0.58137(17) 0.0226(4) Uani 1 1 d . . .
H8A H 0.8067 0.4900 0.5295 0.027 Uiso 1 1 calc R . .
C9 C 0.72623(17) 0.60646(15) 0.58668(17) 0.0235(4) Uani 1 1 d . . .
H9A H 0.7675 0.6489 0.5396 0.028 Uiso 1 1 calc R . .
C10 C 0.64231(18) 0.63830(14) 0.66058(16) 0.0236(4) Uani 1 1 d . . .
H10A H 0.6247 0.7025 0.6627 0.028 Uiso 1 1 calc R . .
C11 C 0.58364(17) 0.57731(13) 0.73164(15) 0.0208(4) Uani 1 1 d . . .
H11A H 0.5261 0.6000 0.7822 0.025 Uiso 1 1 calc R . .
C12 C 0.56270(14) 0.35166(13) 0.99469(15) 0.0145(4) Uani 1 1 d . . .
C13 C 0.61812(16) 0.34435(12) 1.11081(15) 0.0157(4) Uani 1 1 d . . .
C14 C 0.72303(16) 0.38572(14) 1.13110(16) 0.0172(4) Uani 1 1 d . . .
H14A H 0.7594 0.4191 1.0702 0.021 Uiso 1 1 calc R . .
C15 C 0.77521(16) 0.37881(14) 1.23943(16) 0.0203(4) Uani 1 1 d . . .
H15A H 0.8465 0.4079 1.2524 0.024 Uiso 1 1 calc R . .
C16 C 0.72345(17) 0.32956(14) 1.32874(17) 0.0217(4) Uani 1 1 d . . .
H16A H 0.7592 0.3248 1.4028 0.026 Uiso 1 1 calc R . .
C17 C 0.61928(16) 0.28735(14) 1.30947(16) 0.0210(4) Uani 1 1 d . . .
H17A H 0.5837 0.2532 1.3702 0.025 Uiso 1 1 calc R . .
C18 C 0.56697(15) 0.29504(13) 1.20118(15) 0.0182(4) Uani 1 1 d . . .
H18A H 0.4954 0.2663 1.1886 0.022 Uiso 1 1 calc R . .
C19 C 0.29714(15) 0.17405(13) 0.90423(15) 0.0153(4) Uani 1 1 d . . .
C20 C 0.19013(15) 0.12812(13) 0.86613(16) 0.0166(4) Uani 1 1 d . . .
C21 C 0.15759(15) 0.13362(14) 0.74935(16) 0.0201(4) Uani 1 1 d . . .
H21A H 0.2038 0.1658 0.6948 0.024 Uiso 1 1 calc R . .
C22 C 0.05779(16) 0.09201(14) 0.71339(17) 0.0228(4) Uani 1 1 d . . .
H22A H 0.0361 0.0953 0.6337 0.027 Uiso 1 1 calc R . .
C23 C -0.01110(16) 0.04555(14) 0.79232(19) 0.0238(4) Uani 1 1 d . . .
H23A H -0.0796 0.0174 0.7668 0.029 Uiso 1 1 calc R . .
C24 C 0.02060(16) 0.04048(13) 0.90876(18) 0.0217(4) Uani 1 1 d . . .
H24A H -0.0263 0.0089 0.9631 0.026 Uiso 1 1 calc R . .
C25 C 0.12097(15) 0.08166(13) 0.94578(17) 0.0189(4) Uani 1 1 d . . .
H25A H 0.1425 0.0782 1.0255 0.023 Uiso 1 1 calc R . .


_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 C19 1.311(2) . ?
N1 C1 1.380(2) . ?
N2 C12 1.343(2) . ?
N2 C1 1.352(2) . ?
N3 C12 1.335(2) . ?
N3 C5 1.361(2) . ?
N4 C19 1.341(2) . ?
N4 H4A 0.8800 . ?
N4 H4B 0.8800 . ?
C1 C2 1.416(3) . ?
C2 C5 1.387(3) . ?
C2 C3 1.503(2) . ?
C3 C4 1.521(3) . ?
C3 H3B 0.9900 . ?
C3 H3C 0.9900 . ?
C4 H4C 0.9800 . ?
C4 H4D 0.9800 . ?
C4 H4E 0.9800 . ?
C5 C6 1.496(3) . ?
C6 C11 1.392(3) . ?
C6 C7 1.393(3) . ?
C7 C8 1.392(3) . ?
C7 H7A 0.9500 . ?
C8 C9 1.388(3) . ?
C8 H8A 0.9500 . ?
C9 C10 1.381(3) . ?
C9 H9A 0.9500 . ?
C10 C11 1.384(3) . ?
C10 H10A 0.9500 . ?
C11 H11A 0.9500 . ?
C12 C13 1.487(2) . ?
C13 C14 1.392(3) . ?
C13 C18 1.394(2) . ?
C14 C15 1.389(2) . ?
C14 H14A 0.9500 . ?
C15 C16 1.388(3) . ?
C15 H15A 0.9500 . ?
C16 C17 1.388(3) . ?
C16 H16A 0.9500 . ?
C17 C18 1.391(3) . ?
C17 H17A 0.9500 . ?
C18 H18A 0.9500 . ?
C19 C20 1.490(2) . ?
C20 C21 1.395(3) . ?
C20 C25 1.395(3) . ?
C21 C22 1.383(3) . ?
C21 H21A 0.9500 . ?
C22 C23 1.388(3) . ?
C22 H22A 0.9500 . ?
C23 C24 1.388(3) . ?
C23 H23A 0.9500 . ?
C24 C25 1.390(3) . ?
C24 H24A 0.9500 . ?
C25 H25A 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
C19 N1 C1 123.83(15) . . ?
C12 N2 C1 117.75(15) . . ?
C12 N3 C5 115.98(15) . . ?
C19 N4 H4A 120.0 . . ?
C19 N4 H4B 120.0 . . ?
H4A N4 H4B 120.0 . . ?
N2 C1 N1 121.59(16) . . ?
N2 C1 C2 120.97(16) . . ?
N1 C1 C2 117.38(16) . . ?
C5 C2 C1 116.09(15) . . ?
C5 C2 C3 122.33(16) . . ?
C1 C2 C3 121.57(16) . . ?
C2 C3 C4 112.67(16) . . ?
C2 C3 H3B 109.1 . . ?
C4 C3 H3B 109.1 . . ?
C2 C3 H3C 109.1 . . ?
C4 C3 H3C 109.1 . . ?
H3B C3 H3C 107.8 . . ?
C3 C4 H4C 109.5 . . ?
C3 C4 H4D 109.5 . . ?
H4C C4 H4D 109.5 . . ?
C3 C4 H4E 109.5 . . ?
H4C C4 H4E 109.5 . . ?
H4D C4 H4E 109.5 . . ?
N3 C5 C2 123.17(16) . . ?
N3 C5 C6 114.18(16) . . ?
C2 C5 C6 122.65(16) . . ?
C11 C6 C7 118.77(17) . . ?
C11 C6 C5 121.45(17) . . ?
C7 C6 C5 119.66(17) . . ?
C8 C7 C6 120.70(18) . . ?
C8 C7 H7A 119.7 . . ?
C6 C7 H7A 119.7 . . ?
C9 C8 C7 119.69(19) . . ?
C9 C8 H8A 120.2 . . ?
C7 C8 H8A 120.2 . . ?
C10 C9 C8 119.85(19) . . ?
C10 C9 H9A 120.1 . . ?
C8 C9 H9A 120.1 . . ?
C9 C10 C11 120.48(19) . . ?
C9 C10 H10A 119.8 . . ?
C11 C10 H10A 119.8 . . ?
C10 C11 C6 120.46(18) . . ?
C10 C11 H11A 119.8 . . ?
C6 C11 H11A 119.8 . . ?
N3 C12 N2 125.90(15) . . ?
N3 C12 C13 117.50(16) . . ?
N2 C12 C13 116.59(15) . . ?
C14 C13 C18 118.58(16) . . ?
C14 C13 C12 120.60(16) . . ?
C18 C13 C12 120.81(16) . . ?
C15 C14 C13 120.75(17) . . ?
C15 C14 H14A 119.6 . . ?
C13 C14 H14A 119.6 . . ?
C16 C15 C14 120.14(18) . . ?
C16 C15 H15A 119.9 . . ?
C14 C15 H15A 119.9 . . ?
C15 C16 C17 119.73(17) . . ?
C15 C16 H16A 120.1 . . ?
C17 C16 H16A 120.1 . . ?
C16 C17 C18 119.94(18) . . ?
C16 C17 H17A 120.0 . . ?
C18 C17 H17A 120.0 . . ?
C17 C18 C13 120.86(17) . . ?
C17 C18 H18A 119.6 . . ?
C13 C18 H18A 119.6 . . ?
N1 C19 N4 126.71(16) . . ?
N1 C19 C20 116.23(15) . . ?
N4 C19 C20 117.06(16) . . ?
C21 C20 C25 119.67(17) . . ?
C21 C20 C19 119.25(16) . . ?
C25 C20 C19 121.06(16) . . ?
C22 C21 C20 119.67(18) . . ?
C22 C21 H21A 120.2 . . ?
C20 C21 H21A 120.2 . . ?
C21 C22 C23 120.82(18) . . ?
C21 C22 H22A 119.6 . . ?
C23 C22 H22A 119.6 . . ?
C22 C23 C24 119.68(18) . . ?
C22 C23 H23A 120.2 . . ?
C24 C23 H23A 120.2 . . ?
C23 C24 C25 120.00(18) . . ?
C23 C24 H24A 120.0 . . ?
C25 C24 H24A 120.0 . . ?
C24 C25 C20 120.15(17) . . ?
C24 C25 H25A 119.9 . . ?
C20 C25 H25A 119.9 . . ?

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 N2 C1 N1 -174.90(15) . . . . ?
C12 N2 C1 C2 2.3(3) . . . . ?
C19 N1 C1 N2 -16.1(3) . . . . ?
C19 N1 C1 C2 166.55(16) . . . . ?
N2 C1 C2 C5 -0.2(2) . . . . ?
N1 C1 C2 C5 177.17(15) . . . . ?
N2 C1 C2 C3 178.35(16) . . . . ?
N1 C1 C2 C3 -4.3(3) . . . . ?
C5 C2 C3 C4 96.8(2) . . . . ?
C1 C2 C3 C4 -81.6(2) . . . . ?
C12 N3 C5 C2 4.3(2) . . . . ?
C12 N3 C5 C6 -175.16(15) . . . . ?
C1 C2 C5 N3 -3.3(3) . . . . ?
C3 C2 C5 N3 178.19(17) . . . . ?
C1 C2 C5 C6 176.14(16) . . . . ?
C3 C2 C5 C6 -2.4(3) . . . . ?
N3 C5 C6 C11 -81.4(2) . . . . ?
C2 C5 C6 C11 99.1(2) . . . . ?
N3 C5 C6 C7 94.7(2) . . . . ?
C2 C5 C6 C7 -84.8(2) . . . . ?
C11 C6 C7 C8 2.2(3) . . . . ?
C5 C6 C7 C8 -174.03(17) . . . . ?
C6 C7 C8 C9 -0.6(3) . . . . ?
C7 C8 C9 C10 -1.3(3) . . . . ?
C8 C9 C10 C11 1.6(3) . . . . ?
C9 C10 C11 C6 0.0(3) . . . . ?
C7 C6 C11 C10 -1.9(3) . . . . ?
C5 C6 C11 C10 174.28(17) . . . . ?
C5 N3 C12 N2 -2.0(3) . . . . ?
C5 N3 C12 C13 177.36(16) . . . . ?
C1 N2 C12 N3 -1.3(3) . . . . ?
C1 N2 C12 C13 179.39(16) . . . . ?
N3 C12 C13 C14 -14.3(3) . . . . ?
N2 C12 C13 C14 165.08(16) . . . . ?
N3 C12 C13 C18 166.48(16) . . . . ?
N2 C12 C13 C18 -14.1(3) . . . . ?
C18 C13 C14 C15 -0.6(3) . . . . ?
C12 C13 C14 C15 -179.82(17) . . . . ?
C13 C14 C15 C16 0.6(3) . . . . ?
C14 C15 C16 C17 -0.1(3) . . . . ?
C15 C16 C17 C18 -0.4(3) . . . . ?
C16 C17 C18 C13 0.4(3) . . . . ?
C14 C13 C18 C17 0.1(3) . . . . ?
C12 C13 C18 C17 179.33(18) . . . . ?
C1 N1 C19 N4 -1.8(3) . . . . ?
C1 N1 C19 C20 178.02(16) . . . . ?
N1 C19 C20 C21 28.1(3) . . . . ?
N4 C19 C20 C21 -152.03(18) . . . . ?
N1 C19 C20 C25 -150.43(17) . . . . ?
N4 C19 C20 C25 29.4(3) . . . . ?
C25 C20 C21 C22 -0.8(3) . . . . ?
C19 C20 C21 C22 -179.34(17) . . . . ?
C20 C21 C22 C23 0.6(3) . . . . ?
C21 C22 C23 C24 -0.2(3) . . . . ?
C22 C23 C24 C25 -0.1(3) . . . . ?
C23 C24 C25 C20 0.0(3) . . . . ?
C21 C20 C25 C24 0.5(3) . . . . ?
C19 C20 C25 C24 179.02(17) . . . . ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        69.98
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.140
_refine_diff_density_min         -0.170
_refine_diff_density_rms         0.039
####################################################################### 
# 
# 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_Compound5e
_database_code_depnum_ccdc_archive 'CCDC 1956323'
loop_
_audit_author_name
_audit_author_address
'Deguang Huang'
;Fujian Institute of Research on the Structure of Matter, CAS
China
;
_audit_update_record             
;
2019-09-27 deposited with the CCDC.	2020-01-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H15 N3 S'
_chemical_formula_sum            'C16 H15 N3 S'
_chemical_formula_weight         281.37

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1
_symmetry_space_group_name_Hall  '-P 1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   11.8744(3)
_cell_length_b                   14.4778(4)
_cell_length_c                   17.3921(4)
_cell_angle_alpha                89.485(2)
_cell_angle_beta                 80.497(2)
_cell_angle_gamma                72.612(2)
_cell_volume                     2811.59(12)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    23404
_cell_measurement_theta_min      3.9120
_cell_measurement_theta_max      72.4430

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.329
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1184
_exptl_absorpt_coefficient_mu    1.974
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6936
_exptl_absorpt_correction_T_max  0.9252
_exptl_absorpt_process_details   
; 
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018) 
Empirical absorption correction using spherical harmonics, 
 implemented in SCALE3 ABSPACK scaling algorithm. 
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'SuperNova (Cu) X-ray Source'
_diffrn_radiation_monochromator  Mirror
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.5594
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            51242
_diffrn_reflns_av_R_equivalents  0.0508
_diffrn_reflns_av_sigmaI/netI    0.0321
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         3.96
_diffrn_reflns_theta_max         69.99
_reflns_number_total             10645
_reflns_number_gt                9584
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

# start Validation Reply Form
_vrf_PLAT420_Compound5e          
;
PROBLEM:  D-H Without Acceptor  N4 --- H4E      .     Please Check
RESPONSE: The H4E/H10C is one of the hydrogens for the aniline group. The other
          hydrogen atom H4D/H10B was defined pointing to a nitrogen acceptor on 
          the neighbour molecule. Thus the direction of H4E/H10C is constrained   
          to point to space between molecules in term of the bond angle of 
          H4E-N4-H4D / H10B-N10-H10C .
;

# end Validation Reply Form


_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0574P)²+2.2350P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         10645
_refine_ls_number_parameters     888
_refine_ls_number_restraints     692
_refine_ls_R_factor_all          0.0508
_refine_ls_R_factor_gt           0.0450
_refine_ls_wR_factor_ref         0.1272
_refine_ls_wR_factor_gt          0.1242
_refine_ls_goodness_of_fit_ref   1.102
_refine_ls_restrained_S_all      1.087
_refine_ls_shift/su_max          0.001
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.36621(15) -0.26273(12) -0.04868(10) 0.0257(4) Uani 1 1 d . . .
H1A H 0.4132 -0.2981 -0.0183 0.031 Uiso 1 1 calc R . .
H1B H 0.3417 -0.2910 -0.0844 0.031 Uiso 1 1 calc R . .
N2 N 0.37363(14) -0.12863(12) 0.01556(9) 0.0210(3) Uani 1 1 d . A .
N3 N 0.25314(14) 0.03042(12) -0.00708(9) 0.0199(3) Uani 1 1 d . A .
C1 C 0.33183(16) -0.16535(14) -0.04045(11) 0.0208(4) Uani 1 1 d . . .
C2 C 0.25282(16) -0.10536(14) -0.08655(11) 0.0201(4) Uani 1 1 d . . .
C3 C 0.21011(17) -0.15041(15) -0.14980(11) 0.0224(4) Uani 1 1 d . . .
H3B H 0.1366 -0.1035 -0.1626 0.027 Uiso 1 1 calc R . .
H3C H 0.1888 -0.2082 -0.1295 0.027 Uiso 1 1 calc R . .
C4 C 0.30305(19) -0.18064(16) -0.22493(12) 0.0277(4) Uani 1 1 d . . .
H4A H 0.2699 -0.2094 -0.2632 0.042 Uiso 1 1 calc R . .
H4B H 0.3756 -0.2282 -0.2131 0.042 Uiso 1 1 calc R . .
H4C H 0.3229 -0.1236 -0.2465 0.042 Uiso 1 1 calc R . .
C5 C 0.21412(16) -0.00765(14) -0.06480(10) 0.0189(4) Uani 1 1 d . . .
C6 C 0.11904(16) 0.06427(14) -0.09907(11) 0.0197(4) Uani 1 1 d . . .
C7 C 0.01602(18) 0.11909(15) -0.04820(11) 0.0255(4) Uani 1 1 d . . .
H7A H 0.0098 0.1099 0.0063 0.031 Uiso 1 1 calc R . .
C8 C -0.07520(19) 0.18535(16) -0.07607(13) 0.0292(5) Uani 1 1 d . . .
H8A H -0.1444 0.2213 -0.0410 0.035 Uiso 1 1 calc R . .
C9 C -0.06691(18) 0.20009(15) -0.15503(13) 0.0263(4) Uani 1 1 d . . .
H9A H -0.1306 0.2457 -0.1743 0.032 Uiso 1 1 calc R . .
C10 C 0.03385(19) 0.14860(15) -0.20598(12) 0.0259(4) Uani 1 1 d . . .
H10A H 0.0397 0.1596 -0.2602 0.031 Uiso 1 1 calc R . .
C11 C 0.12693(17) 0.08077(15) -0.17853(11) 0.0224(4) Uani 1 1 d . . .
H11A H 0.1961 0.0456 -0.2140 0.027 Uiso 1 1 calc R . .
C12 C 0.33315(16) -0.03204(14) 0.02872(10) 0.0194(4) Uani 1 1 d D . .
C13 C 0.38079(16) 0.00909(14) 0.08819(11) 0.0209(4) Uani 0.822(3) 1 d PDU A 1
C14 C 0.4612(7) -0.0357(5) 0.1348(5) 0.0289(12) Uani 0.822(3) 1 d PU A 1
H14A H 0.4942 -0.1042 0.1342 0.035 Uiso 0.822(3) 1 calc PR A 1
C15 C 0.4917(4) 0.0265(3) 0.1837(3) 0.0229(9) Uani 0.822(3) 1 d PU A 1
H15A H 0.5469 0.0059 0.2188 0.028 Uiso 0.822(3) 1 calc PR A 1
C16 C 0.4305(4) 0.1211(4) 0.1737(3) 0.0216(8) Uani 0.822(3) 1 d PU A 1
H16A H 0.4383 0.1746 0.2012 0.026 Uiso 0.822(3) 1 calc PR A 1
S1 S 0.33764(7) 0.13214(5) 0.10533(5) 0.0206(2) Uani 0.822(3) 1 d PU A 1
C13' C 0.38079(16) 0.00909(14) 0.08819(11) 0.0209(4) Uani 0.178(3) 1 d PDU A 2
C14' C 0.3572(18) 0.1018(14) 0.1005(12) 0.026(2) Uani 0.178(3) 1 d PU A 2
H14B H 0.3080 0.1482 0.0715 0.031 Uiso 0.178(3) 1 calc PR A 2
C15' C 0.412(2) 0.129(2) 0.1624(16) 0.0243(18) Uani 0.178(3) 1 d PU A 2
H15B H 0.4016 0.1930 0.1819 0.029 Uiso 0.178(3) 1 calc PR A 2
C16' C 0.478(3) 0.0499(19) 0.1847(18) 0.0237(19) Uani 0.178(3) 1 d PU A 2
H16C H 0.5254 0.0492 0.2236 0.028 Uiso 0.178(3) 1 calc PR A 2
S1' S 0.4753(8) -0.0570(5) 0.1406(5) 0.0252(11) Uani 0.178(3) 1 d PU A 2
N4 N 0.60444(15) 0.72954(12) 0.04698(10) 0.0262(4) Uani 1 1 d . B .
H4D H 0.5369 0.7677 0.0356 0.031 Uiso 1 1 calc R . .
H4E H 0.6681 0.7497 0.0420 0.031 Uiso 1 1 calc R . .
N5 N 0.61009(14) 0.46120(12) 0.12558(9) 0.0198(3) Uani 1 1 d . B .
N6 N 0.50972(14) 0.61471(12) 0.07825(9) 0.0210(3) Uani 1 1 d . B .
C17 C 0.61042(17) 0.64030(14) 0.07211(11) 0.0208(4) Uani 1 1 d . . .
C18 C 0.71813(16) 0.57656(14) 0.09101(11) 0.0213(4) Uani 0.65(3) 1 d PDU B 1
C19 C 0.8312(5) 0.6063(6) 0.0791(5) 0.0216(9) Uani 0.65(3) 1 d PDU B 1
H19A H 0.8398 0.6367 0.0281 0.026 Uiso 0.65(3) 1 calc PR B 1
H19B H 0.9013 0.5480 0.0781 0.026 Uiso 0.65(3) 1 calc PR B 1
C20 C 0.8295(8) 0.6775(5) 0.1438(7) 0.0292(12) Uani 0.65(3) 1 d PDU B 1
H20A H 0.9035 0.6957 0.1341 0.044 Uiso 0.65(3) 1 calc PR B 1
H20B H 0.8231 0.6470 0.1942 0.044 Uiso 0.65(3) 1 calc PR B 1
H20C H 0.7606 0.7356 0.1446 0.044 Uiso 0.65(3) 1 calc PR B 1
C18' C 0.71813(16) 0.57656(14) 0.09101(11) 0.0213(4) Uani 0.35(3) 1 d PDU B 2
C19' C 0.8231(10) 0.6154(11) 0.0957(9) 0.0242(13) Uani 0.35(3) 1 d PDU B 2
H19C H 0.8950 0.5599 0.0985 0.029 Uiso 0.35(3) 1 calc PR B 2
H19D H 0.8397 0.6485 0.0470 0.029 Uiso 0.35(3) 1 calc PR B 2
C20' C 0.8036(15) 0.6856(10) 0.1647(10) 0.0293(16) Uani 0.35(3) 1 d PDU B 2
H20D H 0.8747 0.7071 0.1633 0.044 Uiso 0.35(3) 1 calc PR B 2
H20E H 0.7898 0.6530 0.2135 0.044 Uiso 0.35(3) 1 calc PR B 2
H20F H 0.7338 0.7418 0.1619 0.044 Uiso 0.35(3) 1 calc PR B 2
C21 C 0.71181(16) 0.48791(14) 0.11758(10) 0.0195(4) Uani 1 1 d . . .
C22 C 0.81770(16) 0.41352(14) 0.14040(11) 0.0201(4) Uani 1 1 d . B .
C23 C 0.91537(18) 0.36348(15) 0.08460(12) 0.0261(4) Uani 1 1 d . . .
H23A H 0.9161 0.3775 0.0311 0.031 Uiso 1 1 calc R B .
C24 C 1.01153(18) 0.29327(16) 0.10684(13) 0.0292(5) Uani 1 1 d . B .
H24A H 1.0772 0.2589 0.0685 0.035 Uiso 1 1 calc R . .
C25 C 1.01150(18) 0.27348(15) 0.18469(13) 0.0281(4) Uani 1 1 d . . .
H25A H 1.0776 0.2259 0.1999 0.034 Uiso 1 1 calc R B .
C26 C 0.91518(19) 0.32288(16) 0.24056(13) 0.0298(5) Uani 1 1 d . B .
H26A H 0.9154 0.3093 0.2941 0.036 Uiso 1 1 calc R . .
C27 C 0.81845(18) 0.39212(15) 0.21850(12) 0.0248(4) Uani 1 1 d . . .
H27A H 0.7522 0.4252 0.2570 0.030 Uiso 1 1 calc R B .
C28 C 0.51485(16) 0.52656(14) 0.10519(10) 0.0194(4) Uani 1 1 d . . .
C29 C 0.40396(17) 0.49950(14) 0.11215(11) 0.0215(4) Uani 0.633(3) 1 d PU B 1
C30 C 0.3035(8) 0.5488(7) 0.0810(7) 0.0247(11) Uani 0.633(3) 1 d PU B 1
H30A H 0.2966 0.6064 0.0531 0.030 Uiso 0.633(3) 1 calc PR B 1
C31 C 0.2105(7) 0.5024(4) 0.0961(5) 0.0250(8) Uani 0.633(3) 1 d PU B 1
H31A H 0.1346 0.5258 0.0802 0.030 Uiso 0.633(3) 1 calc PR B 1
C32 C 0.2461(4) 0.4203(5) 0.1364(4) 0.0238(9) Uani 0.633(3) 1 d PU B 1
H32A H 0.1986 0.3785 0.1507 0.029 Uiso 0.633(3) 1 calc PR B 1
S2 S 0.38748(13) 0.40150(10) 0.15848(7) 0.0236(3) Uani 0.633(3) 1 d PU B 1
C29' C 0.40396(17) 0.49950(14) 0.11215(11) 0.0215(4) Uani 0.367(3) 1 d PDU B 2
C30' C 0.3893(11) 0.4143(7) 0.1418(7) 0.0263(12) Uani 0.367(3) 1 d PDU B 2
H30B H 0.4493 0.3670 0.1629 0.032 Uiso 0.367(3) 1 calc PR B 2
C31' C 0.2736(8) 0.4048(9) 0.1373(8) 0.0256(12) Uani 0.367(3) 1 d PDU B 2
H31B H 0.2453 0.3529 0.1569 0.031 Uiso 0.367(3) 1 calc PR B 2
C32' C 0.2115(11) 0.4810(7) 0.1010(9) 0.0239(12) Uani 0.367(3) 1 d PDU B 2
H32B H 0.1345 0.4871 0.0889 0.029 Uiso 0.367(3) 1 calc PR B 2
S2' S 0.2848(3) 0.5656(3) 0.0788(3) 0.0231(6) Uani 0.367(3) 1 d PDU B 2
N7 N 0.66115(15) 0.15467(12) 0.53066(10) 0.0252(4) Uani 1 1 d . . .
H7B H 0.6178 0.1421 0.4981 0.030 Uiso 1 1 calc R . .
H7C H 0.6879 0.1119 0.5648 0.030 Uiso 1 1 calc R . .
N8 N 0.64222(14) 0.30034(12) 0.47434(9) 0.0202(3) Uani 1 1 d . C .
N9 N 0.74460(13) 0.40888(12) 0.50836(9) 0.0190(3) Uani 1 1 d . C .
C33 C 0.68668(16) 0.23954(14) 0.52829(11) 0.0199(4) Uani 1 1 d . . .
C34 C 0.75950(16) 0.26208(14) 0.57820(11) 0.0197(4) Uani 1 1 d . . .
C35 C 0.80363(17) 0.19243(15) 0.63984(11) 0.0229(4) Uani 1 1 d . . .
H35A H 0.8737 0.2058 0.6557 0.027 Uiso 1 1 calc R . .
H35B H 0.8303 0.1254 0.6170 0.027 Uiso 1 1 calc R . .
C36 C 0.70748(18) 0.19979(16) 0.71251(12) 0.0265(4) Uani 1 1 d . . .
H36A H 0.7407 0.1533 0.7503 0.040 Uiso 1 1 calc R . .
H36B H 0.6385 0.1852 0.6974 0.040 Uiso 1 1 calc R . .
H36C H 0.6819 0.2656 0.7361 0.040 Uiso 1 1 calc R . .
C37 C 0.78688(16) 0.34772(14) 0.56410(10) 0.0180(4) Uani 1 1 d . . .
C38 C 0.87153(16) 0.37876(13) 0.60510(11) 0.0190(4) Uani 1 1 d . . .
C39 C 0.86272(17) 0.38221(14) 0.68729(11) 0.0216(4) Uani 1 1 d . . .
H39A H 0.7995 0.3658 0.7197 0.026 Uiso 1 1 calc R . .
C40 C 0.94700(18) 0.40974(15) 0.71991(12) 0.0255(4) Uani 1 1 d . . .
H40A H 0.9422 0.4103 0.7750 0.031 Uiso 1 1 calc R . .
C41 C 1.03746(18) 0.43635(15) 0.67453(13) 0.0269(4) Uani 1 1 d . . .
H41A H 1.0940 0.4555 0.6982 0.032 Uiso 1 1 calc R . .
C42 C 1.04575(18) 0.43507(16) 0.59460(13) 0.0275(4) Uani 1 1 d . . .
H42A H 1.1081 0.4536 0.5630 0.033 Uiso 1 1 calc R . .
C43 C 0.96367(17) 0.40695(15) 0.56026(11) 0.0226(4) Uani 1 1 d . . .
H43A H 0.9700 0.4068 0.5051 0.027 Uiso 1 1 calc R . .
C44 C 0.67203(16) 0.38263(14) 0.46841(10) 0.0182(4) Uani 1 1 d D . .
C45 C 0.61832(16) 0.45116(14) 0.41186(10) 0.0194(4) Uani 0.786(3) 1 d PU C 1
C46 C 0.5433(9) 0.4412(8) 0.3630(6) 0.0289(16) Uani 0.786(3) 1 d PDU C 1
H46A H 0.5200 0.3844 0.3585 0.035 Uiso 0.786(3) 1 calc PR C 1
C47 C 0.5035(6) 0.5252(4) 0.3193(4) 0.0225(8) Uani 0.786(3) 1 d PU C 1
H47A H 0.4493 0.5317 0.2837 0.027 Uiso 0.786(3) 1 calc PR C 1
C48 C 0.5529(7) 0.5945(5) 0.3350(4) 0.0228(9) Uani 0.786(3) 1 d PU C 1
H48A H 0.5383 0.6551 0.3110 0.027 Uiso 0.786(3) 1 calc PR C 1
S3 S 0.64543(11) 0.56010(7) 0.40385(8) 0.0211(2) Uani 0.786(3) 1 d PDU C 1
C45' C 0.61832(16) 0.45116(14) 0.41186(10) 0.0194(4) Uani 0.214(3) 1 d PDU C 2
C46' C 0.6279(19) 0.5440(10) 0.4035(13) 0.027(2) Uani 0.214(3) 1 d PDU C 2
H46B H 0.6716 0.5704 0.4336 0.032 Uiso 0.214(3) 1 calc PR C 2
C47' C 0.566(3) 0.5957(18) 0.3456(15) 0.024(2) Uani 0.214(3) 1 d PDU C 2
H47B H 0.5642 0.6598 0.3317 0.029 Uiso 0.214(3) 1 calc PR C 2
C48' C 0.511(3) 0.5412(15) 0.3130(17) 0.025(3) Uani 0.214(3) 1 d PDU C 2
H48B H 0.4672 0.5613 0.2716 0.030 Uiso 0.214(3) 1 calc PR C 2
S3' S 0.5284(8) 0.4304(6) 0.3555(6) 0.0252(12) Uani 0.214(3) 1 d PDU C 2
N10 N 0.41254(15) 0.27674(12) 0.44498(10) 0.0255(4) Uani 1 1 d . . .
H10B H 0.4819 0.2787 0.4553 0.031 Uiso 1 1 calc R . .
H10C H 0.3517 0.3301 0.4489 0.031 Uiso 1 1 calc R . .
N11 N 0.38391(14) 0.01548(12) 0.37887(9) 0.0191(3) Uani 1 1 d . D .
N12 N 0.49635(14) 0.11356(12) 0.41849(9) 0.0202(3) Uani 1 1 d . D .
C49 C 0.39946(16) 0.19205(14) 0.42319(10) 0.0192(4) Uani 1 1 d . . .
C50 C 0.28925(16) 0.18640(14) 0.40524(10) 0.0188(4) Uani 1 1 d . . .
C51 C 0.18746(17) 0.27787(15) 0.40326(12) 0.0248(4) Uani 1 1 d . . .
H51A H 0.1801 0.3211 0.4488 0.030 Uiso 1 1 calc R . .
H51B H 0.1116 0.2616 0.4067 0.030 Uiso 1 1 calc R . .
C52 C 0.2084(2) 0.33045(17) 0.32812(14) 0.0362(5) Uani 1 1 d . . .
H52A H 0.1414 0.3897 0.3281 0.054 Uiso 1 1 calc R . .
H52B H 0.2142 0.2881 0.2831 0.054 Uiso 1 1 calc R . .
H52C H 0.2830 0.3473 0.3250 0.054 Uiso 1 1 calc R . .
C53 C 0.28641(16) 0.09555(14) 0.38486(10) 0.0176(4) Uani 1 1 d . . .
C54 C 0.17561(16) 0.07885(13) 0.36625(11) 0.0190(4) Uani 1 1 d . . .
C55 C 0.17274(17) 0.04942(14) 0.29074(11) 0.0214(4) Uani 1 1 d . . .
H55A H 0.2420 0.0386 0.2517 0.026 Uiso 1 1 calc R . .
C56 C 0.06893(19) 0.03586(15) 0.27231(12) 0.0261(4) Uani 1 1 d . . .
H56A H 0.0674 0.0161 0.2206 0.031 Uiso 1 1 calc R . .
C57 C -0.03212(18) 0.05108(16) 0.32910(13) 0.0281(4) Uani 1 1 d . . .
H57A H -0.1031 0.0423 0.3163 0.034 Uiso 1 1 calc R . .
C58 C -0.02965(18) 0.07898(16) 0.40446(13) 0.0301(5) Uani 1 1 d . . .
H58A H -0.0987 0.0885 0.4435 0.036 Uiso 1 1 calc R . .
C59 C 0.07348(18) 0.09314(15) 0.42342(12) 0.0258(4) Uani 1 1 d . . .
H59A H 0.0746 0.1125 0.4753 0.031 Uiso 1 1 calc R . .
C60 C 0.48338(16) 0.02983(14) 0.39514(10) 0.0186(4) Uani 1 1 d . . .
C61 C 0.59117(17) -0.05455(14) 0.38625(11) 0.0218(4) Uani 0.502(3) 1 d PU D 1
C62 C 0.5969(12) -0.1481(9) 0.3598(6) 0.0266(12) Uani 0.502(3) 1 d PU D 1
H62A H 0.5311 -0.1646 0.3458 0.032 Uiso 0.502(3) 1 calc PR D 1
C63 C 0.7153(6) -0.2153(8) 0.3566(7) 0.0269(10) Uani 0.502(3) 1 d PU D 1
H63A H 0.7395 -0.2798 0.3353 0.032 Uiso 0.502(3) 1 calc PR D 1
C64 C 0.7873(9) -0.1752(4) 0.3878(6) 0.0233(12) Uani 0.502(3) 1 d PU D 1
H64A H 0.8661 -0.2098 0.3954 0.028 Uiso 0.502(3) 1 calc PR D 1
S4 S 0.71960(15) -0.05326(18) 0.41230(18) 0.0222(4) Uani 0.502(3) 1 d PU D 1
C61' C 0.59117(17) -0.05455(14) 0.38625(11) 0.0218(4) Uani 0.498(3) 1 d PDU D 2
C62' C 0.6968(7) -0.0580(8) 0.4122(8) 0.0257(13) Uani 0.498(3) 1 d PDU D 2
H62B H 0.7091 -0.0055 0.4386 0.031 Uiso 0.498(3) 1 calc PR D 2
C63' C 0.7847(9) -0.1504(5) 0.3941(6) 0.0250(11) Uani 0.498(3) 1 d PDU D 2
H63B H 0.8641 -0.1665 0.4048 0.030 Uiso 0.498(3) 1 calc PR D 2
C64' C 0.7395(6) -0.2127(8) 0.3594(7) 0.0278(13) Uani 0.498(3) 1 d PDU D 2
H64B H 0.7823 -0.2788 0.3458 0.033 Uiso 0.498(3) 1 calc PR D 2
S4' S 0.5966(3) -0.15744(19) 0.34334(13) 0.0275(5) Uani 0.498(3) 1 d PDU D 2


_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 1.347(3) . ?
N1 H1A 0.8800 . ?
N1 H1B 0.8800 . ?
N2 C1 1.343(3) . ?
N2 C12 1.344(3) . ?
N3 C12 1.334(2) . ?
N3 C5 1.357(3) . ?
C1 C2 1.423(3) . ?
C2 C5 1.385(3) . ?
C2 C3 1.512(3) . ?
C3 C4 1.537(3) . ?
C3 H3B 0.9900 . ?
C3 H3C 0.9900 . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 C6 1.491(2) . ?
C6 C11 1.393(3) . ?
C6 C7 1.409(3) . ?
C7 C8 1.368(3) . ?
C7 H7A 0.9500 . ?
C8 C9 1.380(3) . ?
C8 H8A 0.9500 . ?
C9 C10 1.379(3) . ?
C9 H9A 0.9500 . ?
C10 C11 1.390(3) . ?
C10 H10A 0.9500 . ?
C11 H11A 0.9500 . ?
C12 C13 1.466(3) . ?
C13 C14 1.366(7) . ?
C13 S1 1.714(2) . ?
C14 C15 1.407(11) . ?
C14 H14A 0.9500 . ?
C15 C16 1.371(5) . ?
C15 H15A 0.9500 . ?
C16 S1 1.726(3) . ?
C16 H16A 0.9500 . ?
C14' C15' 1.46(3) . ?
C14' H14B 0.9500 . ?
C15' C16' 1.28(3) . ?
C15' H15B 0.9500 . ?
C16' S1' 1.74(3) . ?
C16' H16C 0.9500 . ?
N4 C17 1.346(3) . ?
N4 H4D 0.8800 . ?
N4 H4E 0.8800 . ?
N5 C28 1.337(2) . ?
N5 C21 1.360(3) . ?
N6 C17 1.342(3) . ?
N6 C28 1.343(3) . ?
C17 C18 1.422(3) . ?
C18 C21 1.379(3) . ?
C18 C19 1.511(5) . ?
C19 C20 1.527(5) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C19' C20' 1.522(8) . ?
C19' H19C 0.9900 . ?
C19' H19D 0.9900 . ?
C20' H20D 0.9800 . ?
C20' H20E 0.9800 . ?
C20' H20F 0.9800 . ?
C21 C22 1.499(2) . ?
C22 C27 1.391(3) . ?
C22 C23 1.397(3) . ?
C23 C24 1.390(3) . ?
C23 H23A 0.9500 . ?
C24 C25 1.381(3) . ?
C24 H24A 0.9500 . ?
C25 C26 1.386(3) . ?
C25 H25A 0.9500 . ?
C26 C27 1.386(3) . ?
C26 H26A 0.9500 . ?
C27 H27A 0.9500 . ?
C28 C29 1.469(3) . ?
C29 C30 1.387(9) . ?
C29 S2 1.672(2) . ?
C30 C31 1.444(12) . ?
C30 H30A 0.9500 . ?
C31 C32 1.365(6) . ?
C31 H31A 0.9500 . ?
C32 S2 1.725(5) . ?
C32 H32A 0.9500 . ?
C30' C31' 1.435(9) . ?
C30' H30B 0.9500 . ?
C31' C32' 1.347(8) . ?
C31' H31B 0.9500 . ?
C32' S2' 1.710(8) . ?
C32' H32B 0.9500 . ?
N7 C33 1.349(3) . ?
N7 H7B 0.8800 . ?
N7 H7C 0.8800 . ?
N8 C44 1.339(3) . ?
N8 C33 1.344(2) . ?
N9 C44 1.330(3) . ?
N9 C37 1.362(2) . ?
C33 C34 1.424(3) . ?
C34 C37 1.383(3) . ?
C34 C35 1.514(2) . ?
C35 C36 1.538(3) . ?
C35 H35A 0.9900 . ?
C35 H35B 0.9900 . ?
C36 H36A 0.9800 . ?
C36 H36B 0.9800 . ?
C36 H36C 0.9800 . ?
C37 C38 1.494(3) . ?
C38 C43 1.397(3) . ?
C38 C39 1.416(3) . ?
C39 C40 1.383(3) . ?
C39 H39A 0.9500 . ?
C40 C41 1.374(3) . ?
C40 H40A 0.9500 . ?
C41 C42 1.377(3) . ?
C41 H41A 0.9500 . ?
C42 C43 1.381(3) . ?
C42 H42A 0.9500 . ?
C43 H43A 0.9500 . ?
C44 C45 1.473(2) . ?
C45 C46 1.366(8) . ?
C45 S3 1.702(2) . ?
C46 C47 1.427(11) . ?
C46 H46A 0.9500 . ?
C47 C48 1.355(6) . ?
C47 H47A 0.9500 . ?
C48 S3 1.727(4) . ?
C48 H48A 0.9500 . ?
C46' C47' 1.419(17) . ?
C46' H46B 0.9500 . ?
C47' C48' 1.348(18) . ?
C47' H47B 0.9500 . ?
C48' S3' 1.730(16) . ?
C48' H48B 0.9500 . ?
N10 C49 1.346(3) . ?
N10 H10B 0.8800 . ?
N10 H10C 0.8800 . ?
N11 C60 1.333(2) . ?
N11 C53 1.362(2) . ?
N12 C60 1.341(3) . ?
N12 C49 1.346(2) . ?
C49 C50 1.420(3) . ?
C50 C53 1.377(3) . ?
C50 C51 1.507(3) . ?
C51 C52 1.529(3) . ?
C51 H51A 0.9900 . ?
C51 H51B 0.9900 . ?
C52 H52A 0.9800 . ?
C52 H52B 0.9800 . ?
C52 H52C 0.9800 . ?
C53 C54 1.492(3) . ?
C54 C55 1.393(3) . ?
C54 C59 1.399(3) . ?
C55 C56 1.392(3) . ?
C55 H55A 0.9500 . ?
C56 C57 1.385(3) . ?
C56 H56A 0.9500 . ?
C57 C58 1.383(3) . ?
C57 H57A 0.9500 . ?
C58 C59 1.391(3) . ?
C58 H58A 0.9500 . ?
C59 H59A 0.9500 . ?
C60 C61 1.469(3) . ?
C61 C62 1.413(12) . ?
C61 S4 1.666(3) . ?
C62 C63 1.444(14) . ?
C62 H62A 0.9500 . ?
C63 C64 1.348(10) . ?
C63 H63A 0.9500 . ?
C64 S4 1.731(6) . ?
C64 H64A 0.9500 . ?
C62' C63' 1.430(8) . ?
C62' H62B 0.9500 . ?
C63' C64' 1.368(8) . ?
C63' H63B 0.9500 . ?
C64' S4' 1.715(6) . ?
C64' H64B 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
C1 N1 H1A 120.0 . . ?
C1 N1 H1B 120.0 . . ?
H1A N1 H1B 120.0 . . ?
C1 N2 C12 116.78(16) . . ?
C12 N3 C5 116.15(17) . . ?
N2 C1 N1 115.87(17) . . ?
N2 C1 C2 122.17(18) . . ?
N1 C1 C2 121.93(18) . . ?
C5 C2 C1 115.07(18) . . ?
C5 C2 C3 124.77(16) . . ?
C1 C2 C3 119.99(17) . . ?
C2 C3 C4 113.73(16) . . ?
C2 C3 H3B 108.8 . . ?
C4 C3 H3B 108.8 . . ?
C2 C3 H3C 108.8 . . ?
C4 C3 H3C 108.8 . . ?
H3B C3 H3C 107.7 . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
N3 C5 C2 123.37(17) . . ?
N3 C5 C6 113.77(17) . . ?
C2 C5 C6 122.73(17) . . ?
C11 C6 C7 118.23(17) . . ?
C11 C6 C5 123.61(17) . . ?
C7 C6 C5 118.16(16) . . ?
C8 C7 C6 121.03(18) . . ?
C8 C7 H7A 119.5 . . ?
C6 C7 H7A 119.5 . . ?
C7 C8 C9 120.14(19) . . ?
C7 C8 H8A 119.9 . . ?
C9 C8 H8A 119.9 . . ?
C10 C9 C8 120.01(18) . . ?
C10 C9 H9A 120.0 . . ?
C8 C9 H9A 120.0 . . ?
C9 C10 C11 120.46(18) . . ?
C9 C10 H10A 119.8 . . ?
C11 C10 H10A 119.8 . . ?
C10 C11 C6 120.11(18) . . ?
C10 C11 H11A 119.9 . . ?
C6 C11 H11A 119.9 . . ?
N3 C12 N2 126.21(18) . . ?
N3 C12 C13 116.55(17) . . ?
N2 C12 C13 117.24(16) . . ?
C14 C13 C12 130.1(4) . . ?
C14 C13 S1 110.2(4) . . ?
C12 C13 S1 119.76(14) . . ?
C13 C14 C15 115.3(5) . . ?
C13 C14 H14A 122.3 . . ?
C15 C14 H14A 122.3 . . ?
C16 C15 C14 110.4(5) . . ?
C16 C15 H15A 124.8 . . ?
C14 C15 H15A 124.8 . . ?
C15 C16 S1 112.4(4) . . ?
C15 C16 H16A 123.8 . . ?
S1 C16 H16A 123.8 . . ?
C13 S1 C16 91.7(2) . . ?
C15' C14' H14B 122.6 . . ?
C16' C15' C14' 106(3) . . ?
C16' C15' H15B 127.2 . . ?
C14' C15' H15B 127.2 . . ?
C15' C16' S1' 117(2) . . ?
C15' C16' H16C 121.5 . . ?
S1' C16' H16C 121.5 . . ?
C17 N4 H4D 120.0 . . ?
C17 N4 H4E 120.0 . . ?
H4D N4 H4E 120.0 . . ?
C28 N5 C21 115.64(16) . . ?
C17 N6 C28 116.53(16) . . ?
N6 C17 N4 116.53(17) . . ?
N6 C17 C18 121.90(18) . . ?
N4 C17 C18 121.57(18) . . ?
C21 C18 C17 115.88(17) . . ?
C21 C18 C19 124.0(3) . . ?
C17 C18 C19 120.1(3) . . ?
C18 C19 C20 111.5(4) . . ?
C18 C19 H19A 109.3 . . ?
C20 C19 H19A 109.3 . . ?
C18 C19 H19B 109.3 . . ?
C20 C19 H19B 109.3 . . ?
H19A C19 H19B 108.0 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C20' C19' H19C 108.6 . . ?
C20' C19' H19D 108.6 . . ?
H19C C19' H19D 107.6 . . ?
C19' C20' H20D 109.5 . . ?
C19' C20' H20E 109.5 . . ?
H20D C20' H20E 109.5 . . ?
C19' C20' H20F 109.5 . . ?
H20D C20' H20F 109.5 . . ?
H20E C20' H20F 109.5 . . ?
N5 C21 C18 123.16(17) . . ?
N5 C21 C22 114.84(16) . . ?
C18 C21 C22 122.00(17) . . ?
C27 C22 C23 118.93(17) . . ?
C27 C22 C21 119.70(17) . . ?
C23 C22 C21 121.36(17) . . ?
C24 C23 C22 120.44(19) . . ?
C24 C23 H23A 119.8 . . ?
C22 C23 H23A 119.8 . . ?
C25 C24 C23 120.0(2) . . ?
C25 C24 H24A 120.0 . . ?
C23 C24 H24A 120.0 . . ?
C24 C25 C26 120.08(18) . . ?
C24 C25 H25A 120.0 . . ?
C26 C25 H25A 120.0 . . ?
C25 C26 C27 120.12(19) . . ?
C25 C26 H26A 119.9 . . ?
C27 C26 H26A 119.9 . . ?
C26 C27 C22 120.46(19) . . ?
C26 C27 H27A 119.8 . . ?
C22 C27 H27A 119.8 . . ?
N5 C28 N6 126.86(18) . . ?
N5 C28 C29 117.03(17) . . ?
N6 C28 C29 116.10(16) . . ?
C30 C29 C28 125.4(5) . . ?
C30 C29 S2 112.3(5) . . ?
C28 C29 S2 122.22(15) . . ?
C29 C30 C31 112.0(8) . . ?
C29 C30 H30A 124.0 . . ?
C31 C30 H30A 124.0 . . ?
C32 C31 C30 111.0(7) . . ?
C32 C31 H31A 124.5 . . ?
C30 C31 H31A 124.5 . . ?
C31 C32 S2 112.1(6) . . ?
C31 C32 H32A 123.9 . . ?
S2 C32 H32A 123.9 . . ?
C29 S2 C32 92.5(3) . . ?
C31' C30' H30B 123.6 . . ?
C32' C31' C30' 109.4(12) . . ?
C32' C31' H31B 125.3 . . ?
C30' C31' H31B 125.3 . . ?
C31' C32' S2' 113.4(10) . . ?
C31' C32' H32B 123.3 . . ?
S2' C32' H32B 123.3 . . ?
C33 N7 H7B 120.0 . . ?
C33 N7 H7C 120.0 . . ?
H7B N7 H7C 120.0 . . ?
C44 N8 C33 116.65(16) . . ?
C44 N9 C37 115.93(16) . . ?
N8 C33 N7 115.90(17) . . ?
N8 C33 C34 121.97(18) . . ?
N7 C33 C34 122.10(17) . . ?
C37 C34 C33 115.42(16) . . ?
C37 C34 C35 124.85(17) . . ?
C33 C34 C35 119.71(17) . . ?
C34 C35 C36 112.92(16) . . ?
C34 C35 H35A 109.0 . . ?
C36 C35 H35A 109.0 . . ?
C34 C35 H35B 109.0 . . ?
C36 C35 H35B 109.0 . . ?
H35A C35 H35B 107.8 . . ?
C35 C36 H36A 109.5 . . ?
C35 C36 H36B 109.5 . . ?
H36A C36 H36B 109.5 . . ?
C35 C36 H36C 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?
N9 C37 C34 123.07(17) . . ?
N9 C37 C38 113.68(16) . . ?
C34 C37 C38 123.15(16) . . ?
C43 C38 C39 118.00(18) . . ?
C43 C38 C37 118.48(17) . . ?
C39 C38 C37 123.52(17) . . ?
C40 C39 C38 119.37(18) . . ?
C40 C39 H39A 120.3 . . ?
C38 C39 H39A 120.3 . . ?
C41 C40 C39 121.52(19) . . ?
C41 C40 H40A 119.2 . . ?
C39 C40 H40A 119.2 . . ?
C40 C41 C42 119.70(19) . . ?
C40 C41 H41A 120.2 . . ?
C42 C41 H41A 120.2 . . ?
C41 C42 C43 120.13(19) . . ?
C41 C42 H42A 119.9 . . ?
C43 C42 H42A 119.9 . . ?
C42 C43 C38 121.25(18) . . ?
C42 C43 H43A 119.4 . . ?
C38 C43 H43A 119.4 . . ?
N9 C44 N8 126.78(16) . . ?
N9 C44 C45 116.80(17) . . ?
N8 C44 C45 116.42(17) . . ?
C46 C45 C44 128.5(5) . . ?
C46 C45 S3 111.9(5) . . ?
C44 C45 S3 119.62(15) . . ?
C45 C46 C47 112.8(7) . . ?
C45 C46 H46A 123.6 . . ?
C47 C46 H46A 123.6 . . ?
C48 C47 C46 111.5(6) . . ?
C48 C47 H47A 124.2 . . ?
C46 C47 H47A 124.2 . . ?
C47 C48 S3 112.3(5) . . ?
C47 C48 H48A 123.8 . . ?
S3 C48 H48A 123.8 . . ?
C45 S3 C48 91.4(2) . . ?
C47' C46' H46B 123.2 . . ?
C48' C47' C46' 110(2) . . ?
C48' C47' H47B 124.8 . . ?
C46' C47' H47B 124.8 . . ?
C47' C48' S3' 112.2(18) . . ?
C47' C48' H48B 123.9 . . ?
S3' C48' H48B 123.9 . . ?
C49 N10 H10B 120.0 . . ?
C49 N10 H10C 120.0 . . ?
H10B N10 H10C 120.0 . . ?
C60 N11 C53 115.81(17) . . ?
C60 N12 C49 116.28(16) . . ?
N12 C49 N10 116.62(17) . . ?
N12 C49 C50 121.88(18) . . ?
N10 C49 C50 121.50(17) . . ?
C53 C50 C49 116.10(17) . . ?
C53 C50 C51 123.98(17) . . ?
C49 C50 C51 119.74(17) . . ?
C50 C51 C52 110.85(17) . . ?
C50 C51 H51A 109.5 . . ?
C52 C51 H51A 109.5 . . ?
C50 C51 H51B 109.5 . . ?
C52 C51 H51B 109.5 . . ?
H51A C51 H51B 108.1 . . ?
C51 C52 H52A 109.5 . . ?
C51 C52 H52B 109.5 . . ?
H52A C52 H52B 109.5 . . ?
C51 C52 H52C 109.5 . . ?
H52A C52 H52C 109.5 . . ?
H52B C52 H52C 109.5 . . ?
N11 C53 C50 122.84(17) . . ?
N11 C53 C54 115.43(16) . . ?
C50 C53 C54 121.72(16) . . ?
C55 C54 C59 119.15(18) . . ?
C55 C54 C53 119.83(17) . . ?
C59 C54 C53 121.02(17) . . ?
C56 C55 C54 120.29(18) . . ?
C56 C55 H55A 119.9 . . ?
C54 C55 H55A 119.9 . . ?
C57 C56 C55 120.16(19) . . ?
C57 C56 H56A 119.9 . . ?
C55 C56 H56A 119.9 . . ?
C58 C57 C56 119.98(19) . . ?
C58 C57 H57A 120.0 . . ?
C56 C57 H57A 120.0 . . ?
C57 C58 C59 120.32(19) . . ?
C57 C58 H58A 119.8 . . ?
C59 C58 H58A 119.8 . . ?
C58 C59 C54 120.10(19) . . ?
C58 C59 H59A 120.0 . . ?
C54 C59 H59A 120.0 . . ?
N11 C60 N12 127.02(17) . . ?
N11 C60 C61 116.99(17) . . ?
N12 C60 C61 115.99(17) . . ?
C62 C61 C60 124.6(6) . . ?
C62 C61 S4 111.5(6) . . ?
C60 C61 S4 123.79(17) . . ?
C61 C62 C63 111.5(10) . . ?
C61 C62 H62A 124.3 . . ?
C63 C62 H62A 124.3 . . ?
C64 C63 C62 111.6(11) . . ?
C64 C63 H63A 124.2 . . ?
C62 C63 H63A 124.2 . . ?
C63 C64 S4 112.2(8) . . ?
C63 C64 H64A 123.9 . . ?
S4 C64 H64A 123.9 . . ?
C61 S4 C64 92.9(4) . . ?
C63' C62' H62B 124.3 . . ?
C64' C63' C62' 111.1(10) . . ?
C64' C63' H63B 124.5 . . ?
C62' C63' H63B 124.5 . . ?
C63' C64' S4' 112.0(8) . . ?
C63' C64' H64B 124.0 . . ?
S4' C64' H64B 124.0 . . ?

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 N2 C1 N1 -175.09(16) . . . . ?
C12 N2 C1 C2 2.8(3) . . . . ?
N2 C1 C2 C5 -5.5(3) . . . . ?
N1 C1 C2 C5 172.33(17) . . . . ?
N2 C1 C2 C3 178.96(17) . . . . ?
N1 C1 C2 C3 -3.2(3) . . . . ?
C5 C2 C3 C4 106.5(2) . . . . ?
C1 C2 C3 C4 -78.4(2) . . . . ?
C12 N3 C5 C2 0.3(3) . . . . ?
C12 N3 C5 C6 176.16(16) . . . . ?
C1 C2 C5 N3 3.9(3) . . . . ?
C3 C2 C5 N3 179.17(17) . . . . ?
C1 C2 C5 C6 -171.67(17) . . . . ?
C3 C2 C5 C6 3.6(3) . . . . ?
N3 C5 C6 C11 125.5(2) . . . . ?
C2 C5 C6 C11 -58.6(3) . . . . ?
N3 C5 C6 C7 -54.0(2) . . . . ?
C2 C5 C6 C7 122.0(2) . . . . ?
C11 C6 C7 C8 1.4(3) . . . . ?
C5 C6 C7 C8 -179.1(2) . . . . ?
C6 C7 C8 C9 -0.6(3) . . . . ?
C7 C8 C9 C10 -0.5(3) . . . . ?
C8 C9 C10 C11 0.8(3) . . . . ?
C9 C10 C11 C6 0.0(3) . . . . ?
C7 C6 C11 C10 -1.1(3) . . . . ?
C5 C6 C11 C10 179.45(19) . . . . ?
C5 N3 C12 N2 -3.5(3) . . . . ?
C5 N3 C12 C13 176.74(16) . . . . ?
C1 N2 C12 N3 1.9(3) . . . . ?
C1 N2 C12 C13 -178.30(16) . . . . ?
N3 C12 C13 C14 179.0(5) . . . . ?
N2 C12 C13 C14 -0.8(6) . . . . ?
N3 C12 C13 S1 -2.7(2) . . . . ?
N2 C12 C13 S1 177.44(14) . . . . ?
C12 C13 C14 C15 177.3(4) . . . . ?
S1 C13 C14 C15 -1.1(8) . . . . ?
C13 C14 C15 C16 0.7(9) . . . . ?
C14 C15 C16 S1 0.0(7) . . . . ?
C14 C13 S1 C16 0.9(5) . . . . ?
C12 C13 S1 C16 -177.7(2) . . . . ?
C15 C16 S1 C13 -0.6(4) . . . . ?
C14' C15' C16' S1' -2(3) . . . . ?
C28 N6 C17 N4 -178.39(17) . . . . ?
C28 N6 C17 C18 1.7(3) . . . . ?
N6 C17 C18 C21 -1.4(3) . . . . ?
N4 C17 C18 C21 178.73(18) . . . . ?
N6 C17 C18 C19 176.7(5) . . . . ?
N4 C17 C18 C19 -3.2(5) . . . . ?
C21 C18 C19 C20 -104.6(5) . . . . ?
C17 C18 C19 C20 77.5(5) . . . . ?
C28 N5 C21 C18 0.6(3) . . . . ?
C28 N5 C21 C22 -179.74(16) . . . . ?
C17 C18 C21 N5 0.2(3) . . . . ?
C19 C18 C21 N5 -177.8(5) . . . . ?
C17 C18 C21 C22 -179.48(17) . . . . ?
C19 C18 C21 C22 2.6(5) . . . . ?
N5 C21 C22 C27 -69.3(2) . . . . ?
C18 C21 C22 C27 110.3(2) . . . . ?
N5 C21 C22 C23 109.5(2) . . . . ?
C18 C21 C22 C23 -70.9(3) . . . . ?
C27 C22 C23 C24 0.2(3) . . . . ?
C21 C22 C23 C24 -178.6(2) . . . . ?
C22 C23 C24 C25 -0.8(3) . . . . ?
C23 C24 C25 C26 0.6(3) . . . . ?
C24 C25 C26 C27 0.2(3) . . . . ?
C25 C26 C27 C22 -0.8(3) . . . . ?
C23 C22 C27 C26 0.6(3) . . . . ?
C21 C22 C27 C26 179.42(19) . . . . ?
C21 N5 C28 N6 -0.2(3) . . . . ?
C21 N5 C28 C29 179.23(16) . . . . ?
C17 N6 C28 N5 -0.9(3) . . . . ?
C17 N6 C28 C29 179.63(16) . . . . ?
N5 C28 C29 C30 -167.5(6) . . . . ?
N6 C28 C29 C30 12.0(6) . . . . ?
N5 C28 C29 S2 11.1(2) . . . . ?
N6 C28 C29 S2 -169.33(15) . . . . ?
C28 C29 C30 C31 178.4(6) . . . . ?
S2 C29 C30 C31 -0.4(10) . . . . ?
C29 C30 C31 C32 -1.0(12) . . . . ?
C30 C31 C32 S2 1.9(9) . . . . ?
C30 C29 S2 C32 1.3(6) . . . . ?
C28 C29 S2 C32 -177.6(3) . . . . ?
C31 C32 S2 C29 -1.9(5) . . . . ?
C30' C31' C32' S2' -4.1(14) . . . . ?
C44 N8 C33 N7 -176.55(16) . . . . ?
C44 N8 C33 C34 1.5(3) . . . . ?
N8 C33 C34 C37 -3.7(3) . . . . ?
N7 C33 C34 C37 174.24(17) . . . . ?
N8 C33 C34 C35 177.89(17) . . . . ?
N7 C33 C34 C35 -4.2(3) . . . . ?
C37 C34 C35 C36 103.0(2) . . . . ?
C33 C34 C35 C36 -78.8(2) . . . . ?
C44 N9 C37 C34 1.4(3) . . . . ?
C44 N9 C37 C38 177.83(15) . . . . ?
C33 C34 C37 N9 2.2(3) . . . . ?
C35 C34 C37 N9 -179.52(17) . . . . ?
C33 C34 C37 C38 -173.91(16) . . . . ?
C35 C34 C37 C38 4.4(3) . . . . ?
N9 C37 C38 C43 -47.2(2) . . . . ?
C34 C37 C38 C43 129.2(2) . . . . ?
N9 C37 C38 C39 132.09(18) . . . . ?
C34 C37 C38 C39 -51.5(3) . . . . ?
C43 C38 C39 C40 -2.2(3) . . . . ?
C37 C38 C39 C40 178.48(17) . . . . ?
C38 C39 C40 C41 1.7(3) . . . . ?
C39 C40 C41 C42 -0.5(3) . . . . ?
C40 C41 C42 C43 -0.2(3) . . . . ?
C41 C42 C43 C38 -0.4(3) . . . . ?
C39 C38 C43 C42 1.6(3) . . . . ?
C37 C38 C43 C42 -179.08(18) . . . . ?
C37 N9 C44 N8 -4.1(3) . . . . ?
C37 N9 C44 C45 175.67(15) . . . . ?
C33 N8 C44 N9 2.7(3) . . . . ?
C33 N8 C44 C45 -177.11(16) . . . . ?
N9 C44 C45 C46 178.7(7) . . . . ?
N8 C44 C45 C46 -1.5(7) . . . . ?
N9 C44 C45 S3 -3.0(2) . . . . ?
N8 C44 C45 S3 176.82(14) . . . . ?
C44 C45 C46 C47 176.6(5) . . . . ?
S3 C45 C46 C47 -1.8(10) . . . . ?
C45 C46 C47 C48 1.9(12) . . . . ?
C46 C47 C48 S3 -1.1(10) . . . . ?
C46 C45 S3 C48 1.0(6) . . . . ?
C44 C45 S3 C48 -177.6(3) . . . . ?
C47 C48 S3 C45 0.1(6) . . . . ?
C46' C47' C48' S3' 3(4) . . . . ?
C60 N12 C49 N10 -178.62(16) . . . . ?
C60 N12 C49 C50 0.6(3) . . . . ?
N12 C49 C50 C53 1.7(3) . . . . ?
N10 C49 C50 C53 -179.04(17) . . . . ?
N12 C49 C50 C51 -173.61(17) . . . . ?
N10 C49 C50 C51 5.6(3) . . . . ?
C53 C50 C51 C52 -98.0(2) . . . . ?
C49 C50 C51 C52 76.9(2) . . . . ?
C60 N11 C53 C50 0.9(2) . . . . ?
C60 N11 C53 C54 179.78(15) . . . . ?
C49 C50 C53 N11 -2.5(3) . . . . ?
C51 C50 C53 N11 172.57(17) . . . . ?
C49 C50 C53 C54 178.66(16) . . . . ?
C51 C50 C53 C54 -6.2(3) . . . . ?
N11 C53 C54 C55 -65.2(2) . . . . ?
C50 C53 C54 C55 113.7(2) . . . . ?
N11 C53 C54 C59 115.4(2) . . . . ?
C50 C53 C54 C59 -65.7(2) . . . . ?
C59 C54 C55 C56 0.9(3) . . . . ?
C53 C54 C55 C56 -178.47(17) . . . . ?
C54 C55 C56 C57 -0.3(3) . . . . ?
C55 C56 C57 C58 -0.6(3) . . . . ?
C56 C57 C58 C59 0.9(3) . . . . ?
C57 C58 C59 C54 -0.2(3) . . . . ?
C55 C54 C59 C58 -0.7(3) . . . . ?
C53 C54 C59 C58 178.74(18) . . . . ?
C53 N11 C60 N12 1.9(3) . . . . ?
C53 N11 C60 C61 -177.72(15) . . . . ?
C49 N12 C60 N11 -2.6(3) . . . . ?
C49 N12 C60 C61 176.97(15) . . . . ?
N11 C60 C61 C62 1.9(6) . . . . ?
N12 C60 C61 C62 -177.8(6) . . . . ?
N11 C60 C61 S4 -173.61(19) . . . . ?
N12 C60 C61 S4 6.8(3) . . . . ?
C60 C61 C62 C63 179.4(7) . . . . ?
S4 C61 C62 C63 -4.6(11) . . . . ?
C61 C62 C63 C64 6.9(14) . . . . ?
C62 C63 C64 S4 -6.0(13) . . . . ?
C62 C61 S4 C64 1.1(6) . . . . ?
C60 C61 S4 C64 177.1(4) . . . . ?
C63 C64 S4 C61 3.0(8) . . . . ?
C62' C63' C64' S4' 3.9(13) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        69.99
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.500
_refine_diff_density_min         -0.292
_refine_diff_density_rms         0.055
####################################################################### 
# 
# 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_Compound3c
_database_code_depnum_ccdc_archive 'CCDC 1956321'
loop_
_audit_author_name
_audit_author_address
'Deguang Huang'
;Fujian Institute of Research on the Structure of Matter, CAS
China
;
_audit_update_record             
;
2019-09-27 deposited with the CCDC.	2020-01-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H11 N3'
_chemical_formula_sum            'C14 H11 N3'
_chemical_formula_weight         221.26

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P21/c
_symmetry_space_group_name_Hall  '-P 2ybc'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   12.3235(3)
_cell_length_b                   14.5512(3)
_cell_length_c                   13.9300(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 109.772(3)
_cell_angle_gamma                90.00
_cell_volume                     2350.69(9)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    5428
_cell_measurement_theta_min      3.7800
_cell_measurement_theta_max      72.3340

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.250
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             928
_exptl_absorpt_coefficient_mu    0.607
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8388
_exptl_absorpt_correction_T_max  0.8882
_exptl_absorpt_process_details   
; 
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018) 
Empirical absorption correction using spherical harmonics, 
 implemented in SCALE3 ABSPACK scaling algorithm. 
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'SuperNova (Cu) X-ray Source'
_diffrn_radiation_monochromator  Mirror
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.5594
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            9386
_diffrn_reflns_av_R_equivalents  0.0147
_diffrn_reflns_av_sigmaI/netI    0.0163
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.81
_diffrn_reflns_theta_max         69.93
_reflns_number_total             4423
_reflns_number_gt                4003
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0477P)²+0.5330P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4423
_refine_ls_number_parameters     307
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0382
_refine_ls_R_factor_gt           0.0350
_refine_ls_wR_factor_ref         0.0917
_refine_ls_wR_factor_gt          0.0896
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_restrained_S_all      1.058
_refine_ls_shift/su_max          0.001
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.99798(10) 0.26487(8) -0.04002(8) 0.0233(2) Uani 1 1 d . . .
C2 C 0.96480(9) 0.19874(7) 0.01981(8) 0.0204(2) Uani 1 1 d . . .
C3 C 0.90966(9) 0.11509(7) -0.03405(8) 0.0208(2) Uani 1 1 d . . .
C4 C 0.89717(9) 0.10057(8) -0.13700(8) 0.0249(2) Uani 1 1 d . . .
H4A H 0.9223 0.1458 -0.1739 0.030 Uiso 1 1 calc R . .
C5 C 0.84806(10) 0.01997(8) -0.18383(8) 0.0270(3) Uani 1 1 d . . .
H5A H 0.8397 0.0089 -0.2532 0.032 Uiso 1 1 calc R . .
C6 C 0.81104(9) -0.04474(8) -0.12873(9) 0.0270(2) Uani 1 1 d . . .
H6A H 0.7759 -0.1004 -0.1595 0.032 Uiso 1 1 calc R . .
C7 C 0.82670(9) -0.02597(8) -0.02791(9) 0.0252(2) Uani 1 1 d . . .
H7A H 0.8020 -0.0706 0.0101 0.030 Uiso 1 1 calc R . .
C8 C 0.99775(9) 0.21302(7) 0.12480(8) 0.0192(2) Uani 1 1 d . . .
C9 C 1.06082(9) 0.29764(7) 0.17289(8) 0.0200(2) Uani 1 1 d . . .
C10 C 1.16377(10) 0.28959(8) 0.25529(8) 0.0240(2) Uani 1 1 d . . .
H10A H 1.1916 0.2306 0.2813 0.029 Uiso 1 1 calc R . .
C11 C 1.22518(10) 0.36756(9) 0.29898(9) 0.0308(3) Uani 1 1 d . . .
H11A H 1.2958 0.3617 0.3542 0.037 Uiso 1 1 calc R . .
C12 C 1.18438(12) 0.45415(8) 0.26274(10) 0.0330(3) Uani 1 1 d . . .
H12A H 1.2271 0.5074 0.2927 0.040 Uiso 1 1 calc R . .
C13 C 1.08088(12) 0.46265(8) 0.18251(9) 0.0314(3) Uani 1 1 d . . .
H13A H 1.0519 0.5219 0.1583 0.038 Uiso 1 1 calc R . .
C14 C 1.01983(10) 0.38481(8) 0.13761(8) 0.0252(2) Uani 1 1 d . . .
H14A H 0.9494 0.3910 0.0823 0.030 Uiso 1 1 calc R . .
C15 C 0.47739(9) -0.03182(7) 0.26353(8) 0.0233(2) Uani 1 1 d . . .
C16 C 0.44976(9) 0.04725(7) 0.31081(8) 0.0209(2) Uani 1 1 d . . .
C17 C 0.38919(9) 0.02978(7) 0.38362(8) 0.0215(2) Uani 1 1 d . . .
C18 C 0.36987(9) -0.06015(8) 0.41030(8) 0.0242(2) Uani 1 1 d . . .
H18A H 0.3969 -0.1112 0.3823 0.029 Uiso 1 1 calc R . .
C19 C 0.31109(10) -0.07366(9) 0.47765(9) 0.0288(3) Uani 1 1 d . . .
H19A H 0.2974 -0.1342 0.4964 0.035 Uiso 1 1 calc R . .
C20 C 0.27215(10) 0.00149(9) 0.51776(9) 0.0322(3) Uani 1 1 d . . .
H20A H 0.2309 -0.0062 0.5638 0.039 Uiso 1 1 calc R . .
C21 C 0.29524(11) 0.08785(9) 0.48858(9) 0.0320(3) Uani 1 1 d . . .
H21A H 0.2692 0.1396 0.5163 0.038 Uiso 1 1 calc R . .
C22 C 0.48356(9) 0.13309(7) 0.28725(8) 0.0219(2) Uani 1 1 d . . .
C23 C 0.54336(9) 0.14459(7) 0.21144(8) 0.0225(2) Uani 1 1 d . . .
C24 C 0.64494(10) 0.19611(8) 0.23731(9) 0.0272(2) Uani 1 1 d . . .
H24A H 0.6757 0.2228 0.3032 0.033 Uiso 1 1 calc R . .
C25 C 0.70087(10) 0.20839(8) 0.16709(10) 0.0320(3) Uani 1 1 d . . .
H25A H 0.7705 0.2428 0.1855 0.038 Uiso 1 1 calc R . .
C26 C 0.65599(11) 0.17090(8) 0.07037(10) 0.0326(3) Uani 1 1 d . . .
H26A H 0.6947 0.1794 0.0225 0.039 Uiso 1 1 calc R . .
C27 C 0.55400(11) 0.12068(8) 0.04338(9) 0.0304(3) Uani 1 1 d . . .
H27A H 0.5225 0.0955 -0.0233 0.036 Uiso 1 1 calc R . .
C28 C 0.49831(10) 0.10731(8) 0.11365(9) 0.0256(2) Uani 1 1 d . . .
H28A H 0.4290 0.0725 0.0951 0.031 Uiso 1 1 calc R . .
N1 N 1.02234(10) 0.31503(7) -0.09358(7) 0.0316(2) Uani 1 1 d . . .
N2 N 0.87470(8) 0.05157(6) 0.01964(7) 0.0225(2) Uani 1 1 d . . .
N3 N 0.97867(8) 0.15114(6) 0.18746(6) 0.0218(2) Uani 1 1 d . . .
H3A H 0.9441 0.0990 0.1630 0.026 Uiso 1 1 calc R . .
H3B H 1.0006 0.1623 0.2534 0.026 Uiso 1 1 calc R . .
N4 N 0.49604(9) -0.09861(7) 0.22746(8) 0.0311(2) Uani 1 1 d . . .
N5 N 0.35227(8) 0.10320(7) 0.42337(7) 0.0273(2) Uani 1 1 d . . .
N6 N 0.46746(9) 0.20996(6) 0.33296(7) 0.0276(2) Uani 1 1 d . . .
H6B H 0.4344 0.2074 0.3799 0.033 Uiso 1 1 calc R . .
H6C H 0.4899 0.2632 0.3162 0.033 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.1537(15) . ?
C1 C2 1.4208(15) . ?
C2 C8 1.3947(14) . ?
C2 C3 1.4701(15) . ?
C3 N2 1.3482(14) . ?
C3 C4 1.4056(15) . ?
C4 C5 1.3784(16) . ?
C4 H4A 0.9500 . ?
C5 C6 1.3859(17) . ?
C5 H5A 0.9500 . ?
C6 C7 1.3787(16) . ?
C6 H6A 0.9500 . ?
C7 N2 1.3404(14) . ?
C7 H7A 0.9500 . ?
C8 N3 1.3291(13) . ?
C8 C9 1.4889(15) . ?
C9 C14 1.3920(15) . ?
C9 C10 1.3984(15) . ?
C10 C11 1.3851(16) . ?
C10 H10A 0.9500 . ?
C11 C12 1.3870(18) . ?
C11 H11A 0.9500 . ?
C12 C13 1.3881(19) . ?
C12 H12A 0.9500 . ?
C13 C14 1.3863(17) . ?
C13 H13A 0.9500 . ?
C14 H14A 0.9500 . ?
C15 N4 1.1524(15) . ?
C15 C16 1.4231(15) . ?
C16 C22 1.3906(15) . ?
C16 C17 1.4706(15) . ?
C17 N5 1.3512(14) . ?
C17 C18 1.4025(15) . ?
C18 C19 1.3796(16) . ?
C18 H18A 0.9500 . ?
C19 C20 1.3855(18) . ?
C19 H19A 0.9500 . ?
C20 C21 1.3798(18) . ?
C20 H20A 0.9500 . ?
C21 N5 1.3420(15) . ?
C21 H21A 0.9500 . ?
C22 N6 1.3346(14) . ?
C22 C23 1.4876(15) . ?
C23 C28 1.3951(16) . ?
C23 C24 1.3978(16) . ?
C24 C25 1.3858(17) . ?
C24 H24A 0.9500 . ?
C25 C26 1.3837(19) . ?
C25 H25A 0.9500 . ?
C26 C27 1.3911(18) . ?
C26 H26A 0.9500 . ?
C27 C28 1.3863(16) . ?
C27 H27A 0.9500 . ?
C28 H28A 0.9500 . ?
N3 H3A 0.8800 . ?
N3 H3B 0.8800 . ?
N6 H6B 0.8800 . ?
N6 H6C 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
N1 C1 C2 175.85(12) . . ?
C8 C2 C1 118.34(10) . . ?
C8 C2 C3 125.37(10) . . ?
C1 C2 C3 115.88(9) . . ?
N2 C3 C4 121.18(10) . . ?
N2 C3 C2 117.63(9) . . ?
C4 C3 C2 121.16(10) . . ?
C5 C4 C3 119.33(11) . . ?
C5 C4 H4A 120.3 . . ?
C3 C4 H4A 120.3 . . ?
C4 C5 C6 119.35(10) . . ?
C4 C5 H5A 120.3 . . ?
C6 C5 H5A 120.3 . . ?
C7 C6 C5 118.07(11) . . ?
C7 C6 H6A 121.0 . . ?
C5 C6 H6A 121.0 . . ?
N2 C7 C6 123.81(11) . . ?
N2 C7 H7A 118.1 . . ?
C6 C7 H7A 118.1 . . ?
N3 C8 C2 122.30(10) . . ?
N3 C8 C9 116.49(9) . . ?
C2 C8 C9 121.17(9) . . ?
C14 C9 C10 119.09(10) . . ?
C14 C9 C8 121.53(10) . . ?
C10 C9 C8 119.38(9) . . ?
C11 C10 C9 120.08(11) . . ?
C11 C10 H10A 120.0 . . ?
C9 C10 H10A 120.0 . . ?
C10 C11 C12 120.48(11) . . ?
C10 C11 H11A 119.8 . . ?
C12 C11 H11A 119.8 . . ?
C11 C12 C13 119.68(11) . . ?
C11 C12 H12A 120.2 . . ?
C13 C12 H12A 120.2 . . ?
C14 C13 C12 120.07(11) . . ?
C14 C13 H13A 120.0 . . ?
C12 C13 H13A 120.0 . . ?
C13 C14 C9 120.56(11) . . ?
C13 C14 H14A 119.7 . . ?
C9 C14 H14A 119.7 . . ?
N4 C15 C16 176.28(11) . . ?
C22 C16 C15 118.65(10) . . ?
C22 C16 C17 125.48(10) . . ?
C15 C16 C17 115.85(9) . . ?
N5 C17 C18 121.21(10) . . ?
N5 C17 C16 117.76(10) . . ?
C18 C17 C16 121.03(10) . . ?
C19 C18 C17 119.24(11) . . ?
C19 C18 H18A 120.4 . . ?
C17 C18 H18A 120.4 . . ?
C18 C19 C20 119.67(11) . . ?
C18 C19 H19A 120.2 . . ?
C20 C19 H19A 120.2 . . ?
C21 C20 C19 117.76(11) . . ?
C21 C20 H20A 121.1 . . ?
C19 C20 H20A 121.1 . . ?
N5 C21 C20 123.95(11) . . ?
N5 C21 H21A 118.0 . . ?
C20 C21 H21A 118.0 . . ?
N6 C22 C16 122.38(10) . . ?
N6 C22 C23 115.70(10) . . ?
C16 C22 C23 121.90(10) . . ?
C28 C23 C24 119.09(11) . . ?
C28 C23 C22 121.36(10) . . ?
C24 C23 C22 119.52(10) . . ?
C25 C24 C23 120.21(11) . . ?
C25 C24 H24A 119.9 . . ?
C23 C24 H24A 119.9 . . ?
C26 C25 C24 120.40(11) . . ?
C26 C25 H25A 119.8 . . ?
C24 C25 H25A 119.8 . . ?
C25 C26 C27 119.82(11) . . ?
C25 C26 H26A 120.1 . . ?
C27 C26 H26A 120.1 . . ?
C28 C27 C26 120.05(11) . . ?
C28 C27 H27A 120.0 . . ?
C26 C27 H27A 120.0 . . ?
C27 C28 C23 120.42(11) . . ?
C27 C28 H28A 119.8 . . ?
C23 C28 H28A 119.8 . . ?
C7 N2 C3 118.25(9) . . ?
C8 N3 H3A 120.0 . . ?
C8 N3 H3B 120.0 . . ?
H3A N3 H3B 120.0 . . ?
C21 N5 C17 118.15(10) . . ?
C22 N6 H6B 120.0 . . ?
C22 N6 H6C 120.0 . . ?
H6B N6 H6C 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
N1 C1 C2 C8 172.9(16) . . . . ?
N1 C1 C2 C3 -0.2(17) . . . . ?
C8 C2 C3 N2 8.87(15) . . . . ?
C1 C2 C3 N2 -178.61(9) . . . . ?
C8 C2 C3 C4 -169.16(10) . . . . ?
C1 C2 C3 C4 3.36(14) . . . . ?
N2 C3 C4 C5 0.13(16) . . . . ?
C2 C3 C4 C5 178.09(10) . . . . ?
C3 C4 C5 C6 0.58(16) . . . . ?
C4 C5 C6 C7 -0.93(16) . . . . ?
C5 C6 C7 N2 0.62(17) . . . . ?
C1 C2 C8 N3 -174.36(10) . . . . ?
C3 C2 C8 N3 -2.00(17) . . . . ?
C1 C2 C8 C9 3.15(15) . . . . ?
C3 C2 C8 C9 175.50(9) . . . . ?
N3 C8 C9 C14 -130.18(11) . . . . ?
C2 C8 C9 C14 52.18(14) . . . . ?
N3 C8 C9 C10 49.96(13) . . . . ?
C2 C8 C9 C10 -127.69(11) . . . . ?
C14 C9 C10 C11 -1.73(16) . . . . ?
C8 C9 C10 C11 178.14(10) . . . . ?
C9 C10 C11 C12 1.10(17) . . . . ?
C10 C11 C12 C13 0.39(18) . . . . ?
C11 C12 C13 C14 -1.24(17) . . . . ?
C12 C13 C14 C9 0.60(17) . . . . ?
C10 C9 C14 C13 0.88(16) . . . . ?
C8 C9 C14 C13 -178.98(10) . . . . ?
N4 C15 C16 C22 -171.4(18) . . . . ?
N4 C15 C16 C17 10.1(19) . . . . ?
C22 C16 C17 N5 7.35(16) . . . . ?
C15 C16 C17 N5 -174.24(9) . . . . ?
C22 C16 C17 C18 -173.04(10) . . . . ?
C15 C16 C17 C18 5.37(15) . . . . ?
N5 C17 C18 C19 0.63(16) . . . . ?
C16 C17 C18 C19 -178.97(9) . . . . ?
C17 C18 C19 C20 0.01(16) . . . . ?
C18 C19 C20 C21 -0.53(17) . . . . ?
C19 C20 C21 N5 0.47(19) . . . . ?
C15 C16 C22 N6 -175.70(10) . . . . ?
C17 C16 C22 N6 2.67(17) . . . . ?
C15 C16 C22 C23 2.41(15) . . . . ?
C17 C16 C22 C23 -179.22(9) . . . . ?
N6 C22 C23 C28 -129.71(11) . . . . ?
C16 C22 C23 C28 52.05(15) . . . . ?
N6 C22 C23 C24 48.31(14) . . . . ?
C16 C22 C23 C24 -129.93(11) . . . . ?
C28 C23 C24 C25 -1.14(16) . . . . ?
C22 C23 C24 C25 -179.20(10) . . . . ?
C23 C24 C25 C26 0.88(17) . . . . ?
C24 C25 C26 C27 0.09(17) . . . . ?
C25 C26 C27 C28 -0.79(17) . . . . ?
C26 C27 C28 C23 0.52(17) . . . . ?
C24 C23 C28 C27 0.44(16) . . . . ?
C22 C23 C28 C27 178.47(10) . . . . ?
C6 C7 N2 C3 0.08(16) . . . . ?
C4 C3 N2 C7 -0.46(15) . . . . ?
C2 C3 N2 C7 -178.49(9) . . . . ?
C20 C21 N5 C17 0.14(18) . . . . ?
C18 C17 N5 C21 -0.69(16) . . . . ?
C16 C17 N5 C21 178.92(10) . . . . ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        69.93
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.149
_refine_diff_density_min         -0.221
_refine_diff_density_rms         0.042
####################################################################### 
# 
# 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_Compound6d
_database_code_depnum_ccdc_archive 'CCDC 1956327'
loop_
_audit_author_name
_audit_author_address
'Deguang Huang'
;Fujian Institute of Research on the Structure of Matter, CAS
China
;
_audit_update_record             
;
2019-09-27 deposited with the CCDC.	2020-01-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H19 N5 S'
_chemical_formula_sum            'C22 H19 N5 S'
_chemical_formula_weight         385.48

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_space_group_name_Hall  '-P 2yn'

loop_
_symmetry_equiv_pos_as_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                   4.05790(12)
_cell_length_b                   20.9622(7)
_cell_length_c                   21.6800(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 91.982(3)
_cell_angle_gamma                90.00
_cell_volume                     1843.05(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2566
_cell_measurement_theta_min      4.0310
_cell_measurement_theta_max      72.0020

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.02
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.389
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             808
_exptl_absorpt_coefficient_mu    1.698
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6298
_exptl_absorpt_correction_T_max  0.9668
_exptl_absorpt_process_details   
; 
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018) 
Empirical absorption correction using spherical harmonics, 
 implemented in SCALE3 ABSPACK scaling algorithm. 
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'SuperNova (Cu) X-ray Source'
_diffrn_radiation_monochromator  Mirror
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.5594
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6613
_diffrn_reflns_av_R_equivalents  0.0222
_diffrn_reflns_av_sigmaI/netI    0.0305
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       3
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         4.08
_diffrn_reflns_theta_max         69.95
_reflns_number_total             3439
_reflns_number_gt                2879
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0642P)²+0.2916P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3439
_refine_ls_number_parameters     290
_refine_ls_number_restraints     145
_refine_ls_R_factor_all          0.0473
_refine_ls_R_factor_gt           0.0377
_refine_ls_wR_factor_ref         0.1081
_refine_ls_wR_factor_gt          0.1014
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_restrained_S_all      1.034
_refine_ls_shift/su_max          0.001
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.7503(4) 0.77356(7) 0.56123(7) 0.0186(3) Uani 1 1 d . . .
C2 C 0.6404(3) 0.70930(7) 0.56169(7) 0.0181(3) Uani 1 1 d . . .
C3 C 0.4259(4) 0.68495(7) 0.50850(7) 0.0196(3) Uani 1 1 d . . .
H3A H 0.2497 0.7166 0.4995 0.023 Uiso 1 1 calc R . .
H3B H 0.3184 0.6450 0.5214 0.023 Uiso 1 1 calc R . .
C4 C 0.6070(4) 0.67199(8) 0.44913(7) 0.0225(3) Uani 1 1 d . . .
H4A H 0.4498 0.6565 0.4172 0.034 Uiso 1 1 calc R . .
H4B H 0.7776 0.6396 0.4570 0.034 Uiso 1 1 calc R . .
H4C H 0.7097 0.7115 0.4351 0.034 Uiso 1 1 calc R . .
C5 C 0.7280(3) 0.67350(7) 0.61381(6) 0.0179(3) Uani 1 1 d . . .
C6 C 0.6376(3) 0.60524(7) 0.62131(6) 0.0183(3) Uani 1 1 d . . .
C7 C 0.7034(4) 0.55939(7) 0.57665(7) 0.0204(3) Uani 1 1 d . . .
H7A H 0.8067 0.5718 0.5399 0.024 Uiso 1 1 calc R . .
C8 C 0.6199(4) 0.49609(7) 0.58535(7) 0.0230(3) Uani 1 1 d . . .
H8A H 0.6680 0.4653 0.5548 0.028 Uiso 1 1 calc R . .
C9 C 0.4663(4) 0.47763(8) 0.63854(7) 0.0239(3) Uani 1 1 d . . .
H9A H 0.4052 0.4343 0.6442 0.029 Uiso 1 1 calc R . .
C10 C 0.4021(4) 0.52229(8) 0.68338(7) 0.0248(3) Uani 1 1 d . . .
H10A H 0.2972 0.5094 0.7198 0.030 Uiso 1 1 calc R . .
C11 C 0.4880(4) 0.58510(7) 0.67589(7) 0.0208(3) Uani 1 1 d . . .
H11A H 0.4467 0.6151 0.7075 0.025 Uiso 1 1 calc R . .
C12 C 0.9916(4) 0.75931(7) 0.65734(6) 0.0186(3) Uani 1 1 d . . .
S1 S 1.3072(3) 0.86381(4) 0.71113(5) 0.0239(2) Uani 0.715(2) 1 d PU A 1
C13 C 1.1837(4) 0.78610(7) 0.70969(7) 0.0205(3) Uani 0.715(2) 1 d PU A 1
C14 C 1.289(2) 0.7556(3) 0.7622(3) 0.0267(9) Uani 0.715(2) 1 d PU A 1
H14A H 1.2431 0.7118 0.7697 0.032 Uiso 0.715(2) 1 calc PR A 1
C15 C 1.4729(17) 0.79426(18) 0.8054(3) 0.0244(7) Uani 0.715(2) 1 d PU A 1
H15A H 1.5623 0.7800 0.8440 0.029 Uiso 0.715(2) 1 calc PR A 1
C16 C 1.5015(12) 0.8549(2) 0.78272(14) 0.0228(7) Uani 0.715(2) 1 d PU A 1
H16A H 1.6153 0.8883 0.8040 0.027 Uiso 0.715(2) 1 calc PR A 1
S1' S 1.2781(12) 0.74305(15) 0.77160(16) 0.0225(6) Uani 0.285(2) 1 d PDU A 2
C13' C 1.1837(4) 0.78610(7) 0.70969(7) 0.0205(3) Uani 0.285(2) 1 d PDU A 2
C14' C 1.298(3) 0.8469(4) 0.7112(6) 0.0249(13) Uani 0.285(2) 1 d PDU A 2
H14B H 1.2665 0.8768 0.6786 0.030 Uiso 0.285(2) 1 calc PR A 2
C15' C 1.472(3) 0.8604(7) 0.7683(4) 0.0247(12) Uani 0.285(2) 1 d PDU A 2
H15B H 1.5679 0.9003 0.7795 0.030 Uiso 0.285(2) 1 calc PR A 2
C16' C 1.479(5) 0.8076(5) 0.8036(7) 0.0251(13) Uani 0.285(2) 1 d PDU A 2
H16B H 1.5867 0.8062 0.8432 0.030 Uiso 0.285(2) 1 calc PR A 2
C17 C 0.7496(4) 0.86816(7) 0.50201(7) 0.0212(3) Uani 1 1 d . . .
C18 C 0.6302(4) 0.89903(8) 0.44296(7) 0.0223(3) Uani 1 1 d . . .
C19 C 0.4622(4) 0.86327(8) 0.39797(8) 0.0280(4) Uani 1 1 d . . .
H19A H 0.4217 0.8191 0.4042 0.034 Uiso 1 1 calc R . .
C20 C 0.3547(4) 0.89318(9) 0.34393(8) 0.0318(4) Uani 1 1 d . . .
H20A H 0.2434 0.8697 0.3120 0.038 Uiso 1 1 calc R . .
C21 C 0.4122(4) 0.95763(9) 0.33727(8) 0.0294(4) Uani 1 1 d . . .
H21A H 0.3372 0.9798 0.3012 0.035 Uiso 1 1 calc R . .
C22 C 0.5823(4) 0.98915(9) 0.38457(8) 0.0305(4) Uani 1 1 d . . .
H22A H 0.6225 1.0335 0.3797 0.037 Uiso 1 1 calc R . .
N1 N 0.6640(3) 0.80868(6) 0.50922(6) 0.0207(3) Uani 1 1 d . . .
N2 N 0.9296(3) 0.79815(6) 0.60900(6) 0.0200(3) Uani 1 1 d . A .
N3 N 0.9006(3) 0.69872(6) 0.66257(6) 0.0193(3) Uani 1 1 d . A .
N4 N 0.9296(4) 0.90469(7) 0.54046(6) 0.0274(3) Uani 1 1 d . . .
H4D H 1.0063 0.8890 0.5758 0.033 Uiso 1 1 calc R . .
H4E H 0.9718 0.9445 0.5306 0.033 Uiso 1 1 calc R . .
N5 N 0.6937(4) 0.96123(7) 0.43667(6) 0.0268(3) 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 N2 1.3473(19) . ?
C1 N1 1.3816(19) . ?
C1 C2 1.419(2) . ?
C2 C5 1.392(2) . ?
C2 C3 1.5095(19) . ?
C3 C4 1.528(2) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 N3 1.3552(19) . ?
C5 C6 1.488(2) . ?
C6 C7 1.397(2) . ?
C6 C11 1.413(2) . ?
C7 C8 1.384(2) . ?
C7 H7A 0.9500 . ?
C8 C9 1.385(2) . ?
C8 H8A 0.9500 . ?
C9 C10 1.381(2) . ?
C9 H9A 0.9500 . ?
C10 C11 1.373(2) . ?
C10 H10A 0.9500 . ?
C11 H11A 0.9500 . ?
C12 N3 1.329(2) . ?
C12 N2 1.344(2) . ?
C12 C13 1.466(2) . ?
S1 C13 1.7043(17) . ?
S1 C16 1.726(3) . ?
C13 C14 1.362(6) . ?
C14 C15 1.429(8) . ?
C14 H14A 0.9500 . ?
C15 C16 1.369(5) . ?
C15 H15A 0.9500 . ?
C16 H16A 0.9500 . ?
S1' C16' 1.714(9) . ?
C14' C15' 1.432(9) . ?
C14' H14B 0.9500 . ?
C15' C16' 1.344(9) . ?
C15' H15B 0.9500 . ?
C16' H16B 0.9500 . ?
C17 N1 1.305(2) . ?
C17 N4 1.331(2) . ?
C17 C18 1.500(2) . ?
C18 N5 1.337(2) . ?
C18 C19 1.390(2) . ?
C19 C20 1.386(2) . ?
C19 H19A 0.9500 . ?
C20 C21 1.379(3) . ?
C20 H20A 0.9500 . ?
C21 C22 1.384(2) . ?
C21 H21A 0.9500 . ?
C22 N5 1.337(2) . ?
C22 H22A 0.9500 . ?
N4 H4D 0.8800 . ?
N4 H4E 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
N2 C1 N1 122.57(13) . . ?
N2 C1 C2 121.29(13) . . ?
N1 C1 C2 116.14(13) . . ?
C5 C2 C1 116.47(13) . . ?
C5 C2 C3 124.20(13) . . ?
C1 C2 C3 119.26(13) . . ?
C2 C3 C4 114.97(12) . . ?
C2 C3 H3A 108.5 . . ?
C4 C3 H3A 108.5 . . ?
C2 C3 H3B 108.5 . . ?
C4 C3 H3B 108.5 . . ?
H3A C3 H3B 107.5 . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
N3 C5 C2 122.24(13) . . ?
N3 C5 C6 114.38(12) . . ?
C2 C5 C6 123.37(13) . . ?
C7 C6 C11 118.23(14) . . ?
C7 C6 C5 122.17(13) . . ?
C11 C6 C5 119.57(13) . . ?
C8 C7 C6 120.78(14) . . ?
C8 C7 H7A 119.6 . . ?
C6 C7 H7A 119.6 . . ?
C7 C8 C9 120.05(15) . . ?
C7 C8 H8A 120.0 . . ?
C9 C8 H8A 120.0 . . ?
C10 C9 C8 119.88(15) . . ?
C10 C9 H9A 120.1 . . ?
C8 C9 H9A 120.1 . . ?
C11 C10 C9 120.80(15) . . ?
C11 C10 H10A 119.6 . . ?
C9 C10 H10A 119.6 . . ?
C10 C11 C6 120.23(14) . . ?
C10 C11 H11A 119.9 . . ?
C6 C11 H11A 119.9 . . ?
N3 C12 N2 126.93(13) . . ?
N3 C12 C13 116.21(13) . . ?
N2 C12 C13 116.85(13) . . ?
C13 S1 C16 92.19(19) . . ?
C14 C13 C12 127.6(3) . . ?
C14 C13 S1 110.5(3) . . ?
C12 C13 S1 121.89(12) . . ?
C13 C14 C15 115.0(5) . . ?
C13 C14 H14A 122.5 . . ?
C15 C14 H14A 122.5 . . ?
C16 C15 C14 109.9(5) . . ?
C16 C15 H15A 125.0 . . ?
C14 C15 H15A 125.0 . . ?
C15 C16 S1 112.4(4) . . ?
C15 C16 H16A 123.8 . . ?
S1 C16 H16A 123.8 . . ?
C15' C14' H14B 124.3 . . ?
C16' C15' C14' 109.2(12) . . ?
C16' C15' H15B 125.4 . . ?
C14' C15' H15B 125.4 . . ?
C15' C16' S1' 114.8(11) . . ?
C15' C16' H16B 122.6 . . ?
S1' C16' H16B 122.6 . . ?
N1 C17 N4 128.10(14) . . ?
N1 C17 C18 115.78(13) . . ?
N4 C17 C18 116.12(14) . . ?
N5 C18 C19 123.08(14) . . ?
N5 C18 C17 116.76(14) . . ?
C19 C18 C17 120.16(14) . . ?
C20 C19 C18 118.79(16) . . ?
C20 C19 H19A 120.6 . . ?
C18 C19 H19A 120.6 . . ?
C21 C20 C19 118.83(16) . . ?
C21 C20 H20A 120.6 . . ?
C19 C20 H20A 120.6 . . ?
C20 C21 C22 118.15(15) . . ?
C20 C21 H21A 120.9 . . ?
C22 C21 H21A 120.9 . . ?
N5 C22 C21 124.23(16) . . ?
N5 C22 H22A 117.9 . . ?
C21 C22 H22A 117.9 . . ?
C17 N1 C1 123.08(13) . . ?
C12 N2 C1 116.68(13) . . ?
C12 N3 C5 116.35(12) . . ?
C17 N4 H4D 120.0 . . ?
C17 N4 H4E 120.0 . . ?
H4D N4 H4E 120.0 . . ?
C22 N5 C18 116.90(14) . . ?

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
N2 C1 C2 C5 0.0(2) . . . . ?
N1 C1 C2 C5 179.66(13) . . . . ?
N2 C1 C2 C3 176.96(13) . . . . ?
N1 C1 C2 C3 -3.3(2) . . . . ?
C5 C2 C3 C4 -108.17(17) . . . . ?
C1 C2 C3 C4 75.07(17) . . . . ?
C1 C2 C5 N3 1.9(2) . . . . ?
C3 C2 C5 N3 -174.96(13) . . . . ?
C1 C2 C5 C6 -179.00(13) . . . . ?
C3 C2 C5 C6 4.2(2) . . . . ?
N3 C5 C6 C7 -128.82(14) . . . . ?
C2 C5 C6 C7 52.0(2) . . . . ?
N3 C5 C6 C11 49.45(18) . . . . ?
C2 C5 C6 C11 -129.73(15) . . . . ?
C11 C6 C7 C8 0.9(2) . . . . ?
C5 C6 C7 C8 179.18(13) . . . . ?
C6 C7 C8 C9 0.6(2) . . . . ?
C7 C8 C9 C10 -1.2(2) . . . . ?
C8 C9 C10 C11 0.2(2) . . . . ?
C9 C10 C11 C6 1.4(2) . . . . ?
C7 C6 C11 C10 -1.9(2) . . . . ?
C5 C6 C11 C10 179.77(13) . . . . ?
N3 C12 C13 C14 2.3(5) . . . . ?
N2 C12 C13 C14 -176.9(5) . . . . ?
N3 C12 C13 S1 -177.83(12) . . . . ?
N2 C12 C13 S1 3.0(2) . . . . ?
C16 S1 C13 C14 0.1(4) . . . . ?
C16 S1 C13 C12 -179.8(2) . . . . ?
C12 C13 C14 C15 179.9(5) . . . . ?
S1 C13 C14 C15 0.0(8) . . . . ?
C13 C14 C15 C16 -0.1(10) . . . . ?
C14 C15 C16 S1 0.2(8) . . . . ?
C13 S1 C16 C15 -0.2(4) . . . . ?
C14' C15' C16' S1' -1.2(19) . . . . ?
N1 C17 C18 N5 175.07(14) . . . . ?
N4 C17 C18 N5 -5.0(2) . . . . ?
N1 C17 C18 C19 -4.8(2) . . . . ?
N4 C17 C18 C19 175.09(15) . . . . ?
N5 C18 C19 C20 0.0(3) . . . . ?
C17 C18 C19 C20 179.94(15) . . . . ?
C18 C19 C20 C21 -1.4(3) . . . . ?
C19 C20 C21 C22 1.5(3) . . . . ?
C20 C21 C22 N5 -0.3(3) . . . . ?
N4 C17 N1 C1 0.9(3) . . . . ?
C18 C17 N1 C1 -179.22(13) . . . . ?
N2 C1 N1 C17 0.3(2) . . . . ?
C2 C1 N1 C17 -179.44(14) . . . . ?
N3 C12 N2 C1 1.5(2) . . . . ?
C13 C12 N2 C1 -179.38(12) . . . . ?
N1 C1 N2 C12 178.78(13) . . . . ?
C2 C1 N2 C12 -1.5(2) . . . . ?
N2 C12 N3 C5 0.2(2) . . . . ?
C13 C12 N3 C5 -178.89(12) . . . . ?
C2 C5 N3 C12 -2.0(2) . . . . ?
C6 C5 N3 C12 178.84(13) . . . . ?
C21 C22 N5 C18 -0.9(3) . . . . ?
C19 C18 N5 C22 1.1(3) . . . . ?
C17 C18 N5 C22 -178.81(15) . . . . ?

_diffrn_measured_fraction_theta_max 0.992
_diffrn_reflns_theta_full        69.95
_diffrn_measured_fraction_theta_full 0.992
_refine_diff_density_max         0.259
_refine_diff_density_min         -0.208
_refine_diff_density_rms         0.048
####################################################################### 
# 
# 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_Compound6c
_database_code_depnum_ccdc_archive 'CCDC 1956326'
loop_
_audit_author_name
_audit_author_address
'Deguang Huang'
;Fujian Institute of Research on the Structure of Matter, CAS
China
;
_audit_update_record             
;
2019-09-27 deposited with the CCDC.	2020-01-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H21 N5'
_chemical_formula_sum            'C24 H21 N5'
_chemical_formula_weight         379.46

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   Pn21a
_symmetry_space_group_name_Hall  'P -2ac -2n'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x+1/2, y, -z+1/2'
'-x+1/2, y+1/2, z+1/2'
'-x, y+1/2, -z'

_cell_length_a                   19.9809(13)
_cell_length_b                   17.0776(11)
_cell_length_c                   5.5951(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1909.2(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    1645
_cell_measurement_theta_min      4.3980
_cell_measurement_theta_max      72.3950

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.320
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             800
_exptl_absorpt_coefficient_mu    0.636
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8321
_exptl_absorpt_correction_T_max  0.9106
_exptl_absorpt_process_details   
; 
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018) 
Empirical absorption correction using spherical harmonics, 
 implemented in SCALE3 ABSPACK scaling algorithm. 
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'SuperNova (Cu) X-ray Source'
_diffrn_radiation_monochromator  Mirror
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.5594
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            4501
_diffrn_reflns_av_R_equivalents  0.0359
_diffrn_reflns_av_sigmaI/netI    0.0547
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -4
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_theta_min         4.43
_diffrn_reflns_theta_max         69.99
_reflns_number_total             2477
_reflns_number_gt                2229
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0555P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.2(6)
_refine_ls_number_reflns         2477
_refine_ls_number_parameters     262
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0499
_refine_ls_R_factor_gt           0.0435
_refine_ls_wR_factor_ref         0.1085
_refine_ls_wR_factor_gt          0.1034
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_restrained_S_all      1.079
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.81713(11) 0.51799(14) 0.9184(4) 0.0221(5) Uani 1 1 d . . .
N2 N 0.71848(11) 0.58126(14) 0.7747(4) 0.0219(5) Uani 1 1 d . . .
N3 N 0.65441(11) 0.51990(13) 0.4678(4) 0.0221(5) Uani 1 1 d . . .
N4 N 0.78410(12) 0.62160(15) 1.1787(4) 0.0255(5) Uani 1 1 d . . .
H4A H 0.7475 0.6329 1.0985 0.031 Uiso 1 1 calc R . .
H4B H 0.7944 0.6484 1.3079 0.031 Uiso 1 1 calc R . .
N5 N 0.89148(11) 0.59386(14) 1.4478(4) 0.0240(5) Uani 1 1 d . . .
C1 C 0.76232(13) 0.52131(16) 0.7681(5) 0.0216(5) Uani 1 1 d . . .
C2 C 0.75567(14) 0.45841(17) 0.6043(5) 0.0213(5) Uani 1 1 d . . .
C3 C 0.80950(13) 0.39597(17) 0.5942(5) 0.0233(6) Uani 1 1 d . . .
H3B H 0.8538 0.4220 0.5879 0.028 Uiso 1 1 calc R . .
H3A H 0.8040 0.3658 0.4444 0.028 Uiso 1 1 calc R . .
C4 C 0.80894(15) 0.33862(18) 0.8060(5) 0.0264(6) Uani 1 1 d . . .
H4C H 0.8448 0.3000 0.7856 0.040 Uiso 1 1 calc R . .
H4D H 0.7657 0.3117 0.8124 0.040 Uiso 1 1 calc R . .
H4E H 0.8160 0.3676 0.9551 0.040 Uiso 1 1 calc R . .
C5 C 0.69839(13) 0.45925(16) 0.4623(5) 0.0210(5) Uani 1 1 d . . .
C6 C 0.67799(13) 0.39615(16) 0.2926(5) 0.0216(6) Uani 1 1 d . . .
C7 C 0.68466(14) 0.31677(18) 0.3444(5) 0.0244(6) Uani 1 1 d . . .
H7A H 0.7061 0.3010 0.4881 0.029 Uiso 1 1 calc R . .
C8 C 0.66014(14) 0.26031(17) 0.1873(5) 0.0256(6) Uani 1 1 d . . .
H8A H 0.6647 0.2063 0.2248 0.031 Uiso 1 1 calc R . .
C9 C 0.62898(14) 0.28271(17) -0.0243(5) 0.0259(6) Uani 1 1 d . . .
H9A H 0.6122 0.2443 -0.1314 0.031 Uiso 1 1 calc R . .
C10 C 0.62265(14) 0.36184(17) -0.0775(5) 0.0245(6) Uani 1 1 d . . .
H10A H 0.6017 0.3774 -0.2222 0.029 Uiso 1 1 calc R . .
C11 C 0.64657(13) 0.41805(18) 0.0782(5) 0.0234(6) Uani 1 1 d . . .
H11A H 0.6417 0.4720 0.0400 0.028 Uiso 1 1 calc R . .
C12 C 0.66655(13) 0.57834(16) 0.6183(5) 0.0204(5) Uani 1 1 d . . .
C13 C 0.61859(13) 0.64459(17) 0.6166(5) 0.0226(6) Uani 1 1 d . . .
C14 C 0.61711(15) 0.70035(17) 0.7968(5) 0.0269(6) Uani 1 1 d . . .
H14A H 0.6486 0.6976 0.9238 0.032 Uiso 1 1 calc R . .
C15 C 0.56974(14) 0.76060(18) 0.7935(5) 0.0285(6) Uani 1 1 d . . .
H15A H 0.5689 0.7983 0.9183 0.034 Uiso 1 1 calc R . .
C16 C 0.52394(14) 0.76537(18) 0.6079(5) 0.0276(6) Uani 1 1 d . . .
H16A H 0.4913 0.8058 0.6068 0.033 Uiso 1 1 calc R . .
C17 C 0.52591(14) 0.71112(17) 0.4242(5) 0.0265(6) Uani 1 1 d . . .
H17A H 0.4955 0.7153 0.2943 0.032 Uiso 1 1 calc R . .
C18 C 0.57229(14) 0.65052(17) 0.4293(5) 0.0248(6) Uani 1 1 d . . .
H18A H 0.5726 0.6128 0.3046 0.030 Uiso 1 1 calc R . .
C19 C 0.82420(13) 0.56360(16) 1.1039(5) 0.0218(6) Uani 1 1 d . . .
C20 C 0.88494(14) 0.54883(17) 1.2526(5) 0.0220(5) Uani 1 1 d . . .
C21 C 0.93059(14) 0.49049(17) 1.1918(5) 0.0249(6) Uani 1 1 d . . .
H21A H 0.9246 0.4599 1.0516 0.030 Uiso 1 1 calc R . .
C22 C 0.98497(14) 0.47816(18) 1.3413(6) 0.0275(6) Uani 1 1 d . . .
H22A H 1.0170 0.4389 1.3045 0.033 Uiso 1 1 calc R . .
C23 C 0.99207(14) 0.52362(18) 1.5445(5) 0.0269(6) Uani 1 1 d . . .
H23A H 1.0287 0.5157 1.6502 0.032 Uiso 1 1 calc R . .
C24 C 0.94462(14) 0.58096(18) 1.5905(5) 0.0265(6) Uani 1 1 d . . .
H24A H 0.9498 0.6126 1.7290 0.032 Uiso 1 1 calc R . .


_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 C19 1.306(3) . ?
N1 C1 1.382(3) . ?
N2 C1 1.348(4) . ?
N2 C12 1.358(3) . ?
N3 C12 1.328(4) . ?
N3 C5 1.359(4) . ?
N4 C19 1.341(4) . ?
N4 H4A 0.8800 . ?
N4 H4B 0.8800 . ?
N5 C20 1.342(4) . ?
N5 C24 1.347(4) . ?
C1 C2 1.418(4) . ?
C2 C5 1.393(4) . ?
C2 C3 1.516(4) . ?
C3 C4 1.538(4) . ?
C3 H3B 0.9900 . ?
C3 H3A 0.9900 . ?
C4 H4C 0.9800 . ?
C4 H4D 0.9800 . ?
C4 H4E 0.9800 . ?
C5 C6 1.493(4) . ?
C6 C7 1.393(4) . ?
C6 C11 1.404(4) . ?
C7 C8 1.394(4) . ?
C7 H7A 0.9500 . ?
C8 C9 1.391(4) . ?
C8 H8A 0.9500 . ?
C9 C10 1.389(4) . ?
C9 H9A 0.9500 . ?
C10 C11 1.382(4) . ?
C10 H10A 0.9500 . ?
C11 H11A 0.9500 . ?
C12 C13 1.483(4) . ?
C13 C14 1.387(4) . ?
C13 C18 1.402(4) . ?
C14 C15 1.398(4) . ?
C14 H14A 0.9500 . ?
C15 C16 1.386(4) . ?
C15 H15A 0.9500 . ?
C16 C17 1.384(4) . ?
C16 H16A 0.9500 . ?
C17 C18 1.389(4) . ?
C17 H17A 0.9500 . ?
C18 H18A 0.9500 . ?
C19 C20 1.493(4) . ?
C20 C21 1.393(4) . ?
C21 C22 1.387(4) . ?
C21 H21A 0.9500 . ?
C22 C23 1.384(4) . ?
C22 H22A 0.9500 . ?
C23 C24 1.387(4) . ?
C23 H23A 0.9500 . ?
C24 H24A 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
C19 N1 C1 123.0(2) . . ?
C1 N2 C12 116.8(2) . . ?
C12 N3 C5 118.0(2) . . ?
C19 N4 H4A 120.0 . . ?
C19 N4 H4B 120.0 . . ?
H4A N4 H4B 120.0 . . ?
C20 N5 C24 117.8(2) . . ?
N2 C1 N1 122.0(2) . . ?
N2 C1 C2 122.1(2) . . ?
N1 C1 C2 115.9(2) . . ?
C5 C2 C1 116.0(2) . . ?
C5 C2 C3 124.7(2) . . ?
C1 C2 C3 119.4(2) . . ?
C2 C3 C4 114.5(2) . . ?
C2 C3 H3B 108.6 . . ?
C4 C3 H3B 108.6 . . ?
C2 C3 H3A 108.6 . . ?
C4 C3 H3A 108.6 . . ?
H3B C3 H3A 107.6 . . ?
C3 C4 H4C 109.5 . . ?
C3 C4 H4D 109.5 . . ?
H4C C4 H4D 109.5 . . ?
C3 C4 H4E 109.5 . . ?
H4C C4 H4E 109.5 . . ?
H4D C4 H4E 109.5 . . ?
N3 C5 C2 121.8(2) . . ?
N3 C5 C6 112.8(2) . . ?
C2 C5 C6 125.4(2) . . ?
C7 C6 C11 118.7(3) . . ?
C7 C6 C5 123.0(2) . . ?
C11 C6 C5 118.2(3) . . ?
C6 C7 C8 120.6(3) . . ?
C6 C7 H7A 119.7 . . ?
C8 C7 H7A 119.7 . . ?
C9 C8 C7 120.3(3) . . ?
C9 C8 H8A 119.9 . . ?
C7 C8 H8A 119.9 . . ?
C10 C9 C8 119.4(3) . . ?
C10 C9 H9A 120.3 . . ?
C8 C9 H9A 120.3 . . ?
C11 C10 C9 120.6(3) . . ?
C11 C10 H10A 119.7 . . ?
C9 C10 H10A 119.7 . . ?
C10 C11 C6 120.5(3) . . ?
C10 C11 H11A 119.7 . . ?
C6 C11 H11A 119.7 . . ?
N3 C12 N2 125.1(2) . . ?
N3 C12 C13 116.8(2) . . ?
N2 C12 C13 118.0(2) . . ?
C14 C13 C18 118.7(3) . . ?
C14 C13 C12 122.2(3) . . ?
C18 C13 C12 119.1(3) . . ?
C13 C14 C15 120.6(3) . . ?
C13 C14 H14A 119.7 . . ?
C15 C14 H14A 119.7 . . ?
C16 C15 C14 120.0(3) . . ?
C16 C15 H15A 120.0 . . ?
C14 C15 H15A 120.0 . . ?
C17 C16 C15 119.9(3) . . ?
C17 C16 H16A 120.1 . . ?
C15 C16 H16A 120.1 . . ?
C16 C17 C18 120.1(3) . . ?
C16 C17 H17A 119.9 . . ?
C18 C17 H17A 119.9 . . ?
C17 C18 C13 120.6(3) . . ?
C17 C18 H18A 119.7 . . ?
C13 C18 H18A 119.7 . . ?
N1 C19 N4 128.6(2) . . ?
N1 C19 C20 115.5(2) . . ?
N4 C19 C20 115.9(2) . . ?
N5 C20 C21 123.0(3) . . ?
N5 C20 C19 115.8(2) . . ?
C21 C20 C19 121.1(3) . . ?
C22 C21 C20 118.3(3) . . ?
C22 C21 H21A 120.8 . . ?
C20 C21 H21A 120.8 . . ?
C23 C22 C21 119.4(3) . . ?
C23 C22 H22A 120.3 . . ?
C21 C22 H22A 120.3 . . ?
C22 C23 C24 118.6(3) . . ?
C22 C23 H23A 120.7 . . ?
C24 C23 H23A 120.7 . . ?
N5 C24 C23 123.0(3) . . ?
N5 C24 H24A 118.5 . . ?
C23 C24 H24A 118.5 . . ?

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
C12 N2 C1 N1 179.9(2) . . . . ?
C12 N2 C1 C2 0.9(4) . . . . ?
C19 N1 C1 N2 12.9(4) . . . . ?
C19 N1 C1 C2 -168.1(2) . . . . ?
N2 C1 C2 C5 -4.6(4) . . . . ?
N1 C1 C2 C5 176.4(2) . . . . ?
N2 C1 C2 C3 175.5(2) . . . . ?
N1 C1 C2 C3 -3.5(4) . . . . ?
C5 C2 C3 C4 -105.9(3) . . . . ?
C1 C2 C3 C4 74.0(3) . . . . ?
C12 N3 C5 C2 -1.7(4) . . . . ?
C12 N3 C5 C6 178.0(2) . . . . ?
C1 C2 C5 N3 5.0(4) . . . . ?
C3 C2 C5 N3 -175.1(2) . . . . ?
C1 C2 C5 C6 -174.7(3) . . . . ?
C3 C2 C5 C6 5.2(4) . . . . ?
N3 C5 C6 C7 -139.5(3) . . . . ?
C2 C5 C6 C7 40.2(4) . . . . ?
N3 C5 C6 C11 36.1(3) . . . . ?
C2 C5 C6 C11 -144.3(3) . . . . ?
C11 C6 C7 C8 -0.5(4) . . . . ?
C5 C6 C7 C8 175.1(2) . . . . ?
C6 C7 C8 C9 0.4(4) . . . . ?
C7 C8 C9 C10 0.1(4) . . . . ?
C8 C9 C10 C11 -0.4(4) . . . . ?
C9 C10 C11 C6 0.3(4) . . . . ?
C7 C6 C11 C10 0.2(4) . . . . ?
C5 C6 C11 C10 -175.6(2) . . . . ?
C5 N3 C12 N2 -2.5(4) . . . . ?
C5 N3 C12 C13 178.7(2) . . . . ?
C1 N2 C12 N3 2.9(4) . . . . ?
C1 N2 C12 C13 -178.3(2) . . . . ?
N3 C12 C13 C14 165.9(3) . . . . ?
N2 C12 C13 C14 -13.1(4) . . . . ?
N3 C12 C13 C18 -12.9(4) . . . . ?
N2 C12 C13 C18 168.1(2) . . . . ?
C18 C13 C14 C15 0.9(4) . . . . ?
C12 C13 C14 C15 -177.9(3) . . . . ?
C13 C14 C15 C16 -0.5(5) . . . . ?
C14 C15 C16 C17 -1.0(5) . . . . ?
C15 C16 C17 C18 2.0(4) . . . . ?
C16 C17 C18 C13 -1.6(4) . . . . ?
C14 C13 C18 C17 0.1(4) . . . . ?
C12 C13 C18 C17 178.9(2) . . . . ?
C1 N1 C19 N4 -2.8(4) . . . . ?
C1 N1 C19 C20 177.0(3) . . . . ?
C24 N5 C20 C21 -0.5(4) . . . . ?
C24 N5 C20 C19 178.2(2) . . . . ?
N1 C19 C20 N5 -178.0(2) . . . . ?
N4 C19 C20 N5 1.8(4) . . . . ?
N1 C19 C20 C21 0.7(4) . . . . ?
N4 C19 C20 C21 -179.5(3) . . . . ?
N5 C20 C21 C22 0.5(4) . . . . ?
C19 C20 C21 C22 -178.1(3) . . . . ?
C20 C21 C22 C23 0.1(4) . . . . ?
C21 C22 C23 C24 -0.7(4) . . . . ?
C20 N5 C24 C23 -0.2(4) . . . . ?
C22 C23 C24 N5 0.8(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        69.99
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.178
_refine_diff_density_min         -0.211
_refine_diff_density_rms         0.047
