# Electronic Supplementary Material (ESI) for Physical Chemistry Chemical Physics.
# This journal is © the Owner Societies 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_nh2nh2
_database_code_depnum_ccdc_archive 'CCDC 2012188'
loop_
_audit_author_name
_audit_author_address
CPIQNH
;Feng Chia University
Taiwan
;
_audit_update_record             
;
2020-06-25 deposited with the CCDC.	2020-09-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C18 H14 N2'
_chemical_formula_sum            'C18 H14 N2'
_chemical_melting_point          ?

_exptl_crystal_description       parallelepiped
_exptl_crystal_colour            colorless
_diffrn_ambient_temperature      150(2)
_chemical_formula_weight         258.31

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.1263(4)
_cell_length_b                   13.1296(8)
_cell_length_c                   15.5168(9)
_cell_angle_alpha                67.0568(19)
_cell_angle_beta                 82.3572(19)
_cell_angle_gamma                75.4351(19)
_cell_volume                     1293.02(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9553
_cell_measurement_theta_min      2.955
_cell_measurement_theta_max      26.389
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.327
_exptl_crystal_F_000             544
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.410
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.090
_exptl_absorpt_coefficient_mu    0.079
_shelx_estimated_absorpt_T_min   0.968
_shelx_estimated_absorpt_T_max   0.993
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7836
_exptl_absorpt_correction_T_max  0.9281
_exptl_absorpt_process_details   'SADABS V2012/1 (Bruker AXS Inc.)'
_exptl_absorpt_special_details   ?
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            25951
_diffrn_reflns_av_unetI/netI     0.0330
_diffrn_reflns_av_R_equivalents  0.0436
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         3.059
_diffrn_reflns_theta_max         26.403
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             5284
_reflns_number_gt                4108
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'APEX2 (Bruker AXS, 2010)'
_computing_cell_refinement       'SAINT V7.34A (Bruker AXS, 2006)'
_computing_data_reduction        'SAINT V7.34A (Bruker AXS, 2006)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1028P)²+3.0032P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5284
_refine_ls_number_parameters     369
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1049
_refine_ls_R_factor_gt           0.0835
_refine_ls_wR_factor_ref         0.2387
_refine_ls_wR_factor_gt          0.2189
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_restrained_S_all      1.041
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.2838(4) 0.7230(2) 0.37553(17) 0.0241(5) Uani 1 1 d . . . . .
N2 N 0.0748(4) 0.6673(2) 0.25637(19) 0.0289(6) Uani 1 1 d . . . . .
H2A H 0.080(6) 0.719(4) 0.282(3) 0.045(11) Uiso 1 1 d . . . . .
H2B H 0.000(6) 0.689(3) 0.213(3) 0.034(10) Uiso 1 1 d . . . . .
C1 C 0.4192(4) 0.6384(2) 0.36416(19) 0.0204(6) Uani 1 1 d . . . . .
C2 C 0.4026(4) 0.5775(2) 0.30567(19) 0.0213(6) Uani 1 1 d . . . . .
C3 C 0.2456(4) 0.5925(2) 0.2521(2) 0.0233(6) Uani 1 1 d . . . . .
C4 C 0.2725(5) 0.5254(3) 0.1976(2) 0.0288(7) Uani 1 1 d . . . . .
H4A H 0.1720 0.5345 0.1590 0.035 Uiso 1 1 calc R U . . .
C5 C 0.4439(5) 0.4461(3) 0.1997(2) 0.0331(7) Uani 1 1 d . . . . .
H5A H 0.4579 0.4019 0.1623 0.040 Uiso 1 1 calc R U . . .
C6 C 0.5968(5) 0.4292(3) 0.2551(2) 0.0286(7) Uani 1 1 d . . . . .
H6A H 0.7124 0.3734 0.2568 0.034 Uiso 1 1 calc R U . . .
C7 C 0.5742(4) 0.4964(2) 0.3076(2) 0.0223(6) Uani 1 1 d . . . . .
C8 C 0.7161(4) 0.4990(2) 0.3708(2) 0.0231(6) Uani 1 1 d . . . . .
H8A H 0.7473 0.4256 0.4239 0.028 Uiso 1 1 calc R U . . .
H8B H 0.8377 0.5170 0.3357 0.028 Uiso 1 1 calc R U . . .
C9 C 0.6082(4) 0.5921(2) 0.40415(19) 0.0209(6) Uani 1 1 d . . . . .
C10 C 0.6554(4) 0.6394(2) 0.46035(19) 0.0232(6) Uani 1 1 d . . . . .
C11 C 0.8339(5) 0.6213(3) 0.5122(2) 0.0287(7) Uani 1 1 d . . . . .
H11A H 0.9459 0.6376 0.4679 0.034 Uiso 1 1 calc R U . . .
H11B H 0.8682 0.5423 0.5575 0.034 Uiso 1 1 calc R U . . .
C12 C 0.7762(5) 0.7064(3) 0.5638(2) 0.0361(8) Uani 1 1 d . . . . .
H12A H 0.7737 0.6654 0.6326 0.043 Uiso 1 1 calc R U . . .
H12B H 0.8691 0.7567 0.5468 0.043 Uiso 1 1 calc R U . . .
C13 C 0.5760(5) 0.7741(3) 0.5312(2) 0.0305(7) Uani 1 1 d . . . . .
C14 C 0.5142(4) 0.7294(3) 0.4735(2) 0.0251(6) Uani 1 1 d . . . . .
C15 C 0.3334(4) 0.7711(3) 0.4319(2) 0.0265(6) Uani 1 1 d . . . . .
C16 C 0.2096(5) 0.8646(3) 0.4492(3) 0.0365(8) Uani 1 1 d . . . . .
H16A H 0.0856 0.8964 0.4226 0.044 Uiso 1 1 calc R U . . .
C17 C 0.2707(6) 0.9091(3) 0.5049(3) 0.0440(9) Uani 1 1 d . . . . .
H17A H 0.1870 0.9722 0.5156 0.053 Uiso 1 1 calc R U . . .
C18 C 0.4530(6) 0.8645(3) 0.5469(2) 0.0400(8) Uani 1 1 d . . . . .
H18A H 0.4899 0.8968 0.5855 0.048 Uiso 1 1 calc R U . . .
N3 N 0.7497(4) 0.8370(2) 0.10906(19) 0.0311(6) Uani 1 1 d . . . . .
N4 N 0.8058(5) 0.6266(3) 0.0788(2) 0.0426(8) Uani 1 1 d . . . . .
H4B H 0.8188 0.5531 0.0954 0.051 Uiso 1 1 calc R U . . .
H4C H 0.7817 0.6571 0.1216 0.051 Uiso 1 1 calc R U . . .
C19 C 0.7691(4) 0.8790(3) 0.0179(2) 0.0323(7) Uani 1 1 d . . . . .
C20 C 0.8077(4) 0.8110(3) -0.0417(3) 0.0359(8) Uani 1 1 d . . . . .
C21 C 0.8228(5) 0.6924(3) -0.0122(3) 0.0389(8) Uani 1 1 d . . . . .
C22 C 0.8611(5) 0.6482(4) -0.0835(3) 0.0513(11) Uani 1 1 d . . . . .
H22A H 0.8741 0.5693 -0.0679 0.062 Uiso 1 1 calc R U . . .
C23 C 0.8800(6) 0.7179(4) -0.1756(3) 0.0527(11) Uani 1 1 d . . . . .
H23A H 0.9063 0.6852 -0.2221 0.063 Uiso 1 1 calc R U . . .
C24 C 0.8619(5) 0.8370(4) -0.2045(3) 0.0520(11) Uani 1 1 d . . . . .
H24A H 0.8744 0.8842 -0.2685 0.062 Uiso 1 1 calc R U . . .
C25 C 0.8248(5) 0.8805(4) -0.1337(3) 0.0406(9) Uani 1 1 d . . . . .
C26 C 0.7977(5) 1.0010(3) -0.1427(2) 0.0380(8) Uani 1 1 d . . . . .
H26A H 0.9152 1.0306 -0.1714 0.046 Uiso 1 1 calc R U . . .
H26B H 0.6854 1.0499 -0.1813 0.046 Uiso 1 1 calc R U . . .
C27 C 0.7624(4) 0.9956(3) -0.04418(19) 0.0226(6) Uani 1 1 d . . . . .
C28 C 0.7294(4) 1.0745(3) -0.0038(2) 0.0317(7) Uani 1 1 d . . . . .
C29 C 0.7125(5) 1.2000(3) -0.0384(3) 0.0388(8) Uani 1 1 d . . . . .
H29A H 0.6021 1.2410 -0.0802 0.047 Uiso 1 1 calc R U . . .
H29B H 0.8329 1.2207 -0.0730 0.047 Uiso 1 1 calc R U . . .
C30 C 0.6778(5) 1.2286(3) 0.0527(3) 0.0386(8) Uani 1 1 d . . . . .
H30A H 0.7821 1.2630 0.0583 0.046 Uiso 1 1 calc R U . . .
H30B H 0.5516 1.2822 0.0515 0.046 Uiso 1 1 calc R U . . .
C31 C 0.6790(5) 1.1192(3) 0.1318(3) 0.0351(8) Uani 1 1 d . . . . .
C32 C 0.7080(4) 1.0302(3) 0.0962(2) 0.0281(7) Uani 1 1 d . . . . .
C33 C 0.7180(4) 0.9183(3) 0.1510(2) 0.0300(7) Uani 1 1 d . . . . .
C34 C 0.6968(5) 0.8872(3) 0.2496(2) 0.0355(8) Uani 1 1 d . . . . .
H34A H 0.7014 0.8108 0.2904 0.043 Uiso 1 1 calc R U . . .
C35 C 0.6687(6) 0.9749(3) 0.2843(3) 0.0412(8) Uani 1 1 d . . . . .
H35A H 0.6547 0.9555 0.3502 0.049 Uiso 1 1 calc R U . . .
C36 C 0.6604(5) 1.0878(4) 0.2275(3) 0.0407(9) Uani 1 1 d . . . . .
H36A H 0.6420 1.1432 0.2548 0.049 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C1 1.328(4) . ?
N1 C15 1.384(4) . ?
N2 C3 1.371(4) . ?
N2 H2A 0.92(4) . ?
N2 H2B 0.83(4) . ?
C1 C9 1.444(4) . ?
C1 C2 1.455(4) . ?
C2 C7 1.401(4) . ?
C2 C3 1.411(4) . ?
C3 C4 1.407(4) . ?
C4 C5 1.385(5) . ?
C4 H4A 0.9500 . ?
C5 C6 1.398(5) . ?
C5 H5A 0.9500 . ?
C6 C7 1.386(4) . ?
C6 H6A 0.9500 . ?
C7 C8 1.514(4) . ?
C8 C9 1.505(4) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.366(4) . ?
C10 C14 1.408(4) . ?
C10 C11 1.514(4) . ?
C11 C12 1.562(5) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.512(5) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C18 1.372(5) . ?
C13 C14 1.409(4) . ?
C14 C15 1.403(4) . ?
C15 C16 1.416(4) . ?
C16 C17 1.379(5) . ?
C16 H16A 0.9500 . ?
C17 C18 1.414(6) . ?
C17 H17A 0.9500 . ?
C18 H18A 0.9500 . ?
N3 C19 1.304(4) . ?
N3 C33 1.412(4) . ?
N4 C21 1.346(5) . ?
N4 H4B 0.8800 . ?
N4 H4C 0.8800 . ?
C19 C27 1.449(4) . ?
C19 C20 1.478(5) . ?
C20 C25 1.370(5) . ?
C20 C21 1.421(5) . ?
C21 C22 1.406(5) . ?
C22 C23 1.374(7) . ?
C22 H22A 0.9500 . ?
C23 C24 1.426(7) . ?
C23 H23A 0.9500 . ?
C24 C25 1.392(5) . ?
C24 H24A 0.9500 . ?
C25 C26 1.497(6) . ?
C26 C27 1.493(4) . ?
C26 H26A 0.9900 . ?
C26 H26B 0.9900 . ?
C27 C28 1.366(5) . ?
C28 C32 1.430(4) . ?
C28 C29 1.498(5) . ?
C29 C30 1.574(5) . ?
C29 H29A 0.9900 . ?
C29 H29B 0.9900 . ?
C30 C31 1.480(5) . ?
C30 H30A 0.9900 . ?
C30 H30B 0.9900 . ?
C31 C36 1.375(5) . ?
C31 C32 1.437(5) . ?
C32 C33 1.371(5) . ?
C33 C34 1.418(4) . ?
C34 C35 1.412(5) . ?
C34 H34A 0.9500 . ?
C35 C36 1.389(6) . ?
C35 H35A 0.9500 . ?
C36 H36A 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 C15 115.1(3) . . ?
C3 N2 H2A 116(3) . . ?
C3 N2 H2B 117(3) . . ?
H2A N2 H2B 117(4) . . ?
N1 C1 C9 127.3(3) . . ?
N1 C1 C2 124.9(3) . . ?
C9 C1 C2 107.7(2) . . ?
C7 C2 C3 121.5(3) . . ?
C7 C2 C1 109.7(2) . . ?
C3 C2 C1 128.8(3) . . ?
N2 C3 C4 122.8(3) . . ?
N2 C3 C2 120.2(3) . . ?
C4 C3 C2 116.9(3) . . ?
C5 C4 C3 120.8(3) . . ?
C5 C4 H4A 119.6 . . ?
C3 C4 H4A 119.6 . . ?
C4 C5 C6 122.1(3) . . ?
C4 C5 H5A 118.9 . . ?
C6 C5 H5A 118.9 . . ?
C7 C6 C5 117.8(3) . . ?
C7 C6 H6A 121.1 . . ?
C5 C6 H6A 121.1 . . ?
C6 C7 C2 120.8(3) . . ?
C6 C7 C8 129.2(3) . . ?
C2 C7 C8 110.0(3) . . ?
C9 C8 C7 103.2(2) . . ?
C9 C8 H8A 111.1 . . ?
C7 C8 H8A 111.1 . . ?
C9 C8 H8B 111.1 . . ?
C7 C8 H8B 111.1 . . ?
H8A C8 H8B 109.1 . . ?
C10 C9 C1 117.2(3) . . ?
C10 C9 C8 133.3(3) . . ?
C1 C9 C8 109.5(2) . . ?
C9 C10 C14 116.5(3) . . ?
C9 C10 C11 134.8(3) . . ?
C14 C10 C11 108.6(3) . . ?
C10 C11 C12 104.8(3) . . ?
C10 C11 H11A 110.8 . . ?
C12 C11 H11A 110.8 . . ?
C10 C11 H11B 110.8 . . ?
C12 C11 H11B 110.8 . . ?
H11A C11 H11B 108.9 . . ?
C13 C12 C11 105.1(3) . . ?
C13 C12 H12A 110.7 . . ?
C11 C12 H12A 110.7 . . ?
C13 C12 H12B 110.7 . . ?
C11 C12 H12B 110.7 . . ?
H12A C12 H12B 108.8 . . ?
C18 C13 C14 118.2(3) . . ?
C18 C13 C12 133.3(3) . . ?
C14 C13 C12 108.5(3) . . ?
C10 C14 C13 112.7(3) . . ?
C10 C14 C15 123.4(3) . . ?
C13 C14 C15 123.8(3) . . ?
N1 C15 C14 120.4(3) . . ?
N1 C15 C16 122.8(3) . . ?
C14 C15 C16 116.8(3) . . ?
C17 C16 C15 119.4(3) . . ?
C17 C16 H16A 120.3 . . ?
C15 C16 H16A 120.3 . . ?
C16 C17 C18 122.7(3) . . ?
C16 C17 H17A 118.7 . . ?
C18 C17 H17A 118.7 . . ?
C13 C18 C17 119.1(3) . . ?
C13 C18 H18A 120.4 . . ?
C17 C18 H18A 120.4 . . ?
C19 N3 C33 114.1(3) . . ?
C21 N4 H4B 120.0 . . ?
C21 N4 H4C 120.0 . . ?
H4B N4 H4C 120.0 . . ?
N3 C19 C27 128.9(3) . . ?
N3 C19 C20 124.3(3) . . ?
C27 C19 C20 106.7(3) . . ?
C25 C20 C21 123.2(3) . . ?
C25 C20 C19 109.5(3) . . ?
C21 C20 C19 127.2(3) . . ?
N4 C21 C22 122.4(4) . . ?
N4 C21 C20 121.7(3) . . ?
C22 C21 C20 115.9(4) . . ?
C23 C22 C21 120.7(4) . . ?
C23 C22 H22A 119.6 . . ?
C21 C22 H22A 119.6 . . ?
C22 C23 C24 122.8(4) . . ?
C22 C23 H23A 118.6 . . ?
C24 C23 H23A 118.6 . . ?
C25 C24 C23 116.3(4) . . ?
C25 C24 H24A 121.8 . . ?
C23 C24 H24A 121.8 . . ?
C20 C25 C24 120.9(4) . . ?
C20 C25 C26 110.8(3) . . ?
C24 C25 C26 128.2(4) . . ?
C27 C26 C25 103.9(3) . . ?
C27 C26 H26A 111.0 . . ?
C25 C26 H26A 111.0 . . ?
C27 C26 H26B 111.0 . . ?
C25 C26 H26B 111.0 . . ?
H26A C26 H26B 109.0 . . ?
C28 C27 C19 117.1(3) . . ?
C28 C27 C26 133.9(3) . . ?
C19 C27 C26 109.0(3) . . ?
C27 C28 C32 115.0(3) . . ?
C27 C28 C29 135.6(3) . . ?
C32 C28 C29 109.4(3) . . ?
C28 C29 C30 104.7(3) . . ?
C28 C29 H29A 110.8 . . ?
C30 C29 H29A 110.8 . . ?
C28 C29 H29B 110.8 . . ?
C30 C29 H29B 110.8 . . ?
H29A C29 H29B 108.9 . . ?
C31 C30 C29 105.8(3) . . ?
C31 C30 H30A 110.6 . . ?
C29 C30 H30A 110.6 . . ?
C31 C30 H30B 110.6 . . ?
C29 C30 H30B 110.6 . . ?
H30A C30 H30B 108.7 . . ?
C36 C31 C32 116.6(3) . . ?
C36 C31 C30 133.9(3) . . ?
C32 C31 C30 109.4(3) . . ?
C33 C32 C28 125.0(3) . . ?
C33 C32 C31 124.4(3) . . ?
C28 C32 C31 110.6(3) . . ?
C32 C33 N3 120.0(3) . . ?
C32 C33 C34 118.4(3) . . ?
N3 C33 C34 121.6(3) . . ?
C35 C34 C33 117.0(3) . . ?
C35 C34 H34A 121.5 . . ?
C33 C34 H34A 121.5 . . ?
C36 C35 C34 123.7(3) . . ?
C36 C35 H35A 118.2 . . ?
C34 C35 H35A 118.2 . . ?
C31 C36 C35 119.9(3) . . ?
C31 C36 H36A 120.1 . . ?
C35 C36 H36A 120.1 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C15 N1 C1 C9 0.4(4) . . . . ?
C15 N1 C1 C2 -177.8(3) . . . . ?
N1 C1 C2 C7 178.1(3) . . . . ?
C9 C1 C2 C7 -0.4(3) . . . . ?
N1 C1 C2 C3 -1.3(5) . . . . ?
C9 C1 C2 C3 -179.8(3) . . . . ?
C7 C2 C3 N2 175.7(3) . . . . ?
C1 C2 C3 N2 -5.0(4) . . . . ?
C7 C2 C3 C4 -2.6(4) . . . . ?
C1 C2 C3 C4 176.8(3) . . . . ?
N2 C3 C4 C5 -176.2(3) . . . . ?
C2 C3 C4 C5 2.0(4) . . . . ?
C3 C4 C5 C6 -0.1(5) . . . . ?
C4 C5 C6 C7 -1.3(5) . . . . ?
C5 C6 C7 C2 0.7(4) . . . . ?
C5 C6 C7 C8 -178.0(3) . . . . ?
C3 C2 C7 C6 1.2(4) . . . . ?
C1 C2 C7 C6 -178.2(3) . . . . ?
C3 C2 C7 C8 -179.8(2) . . . . ?
C1 C2 C7 C8 0.8(3) . . . . ?
C6 C7 C8 C9 178.1(3) . . . . ?
C2 C7 C8 C9 -0.8(3) . . . . ?
N1 C1 C9 C10 0.1(4) . . . . ?
C2 C1 C9 C10 178.6(2) . . . . ?
N1 C1 C9 C8 -178.5(3) . . . . ?
C2 C1 C9 C8 -0.1(3) . . . . ?
C7 C8 C9 C10 -177.9(3) . . . . ?
C7 C8 C9 C1 0.5(3) . . . . ?
C1 C9 C10 C14 -0.1(4) . . . . ?
C8 C9 C10 C14 178.1(3) . . . . ?
C1 C9 C10 C11 -177.3(3) . . . . ?
C8 C9 C10 C11 0.9(6) . . . . ?
C9 C10 C11 C12 -178.8(3) . . . . ?
C14 C10 C11 C12 3.8(3) . . . . ?
C10 C11 C12 C13 -4.8(3) . . . . ?
C11 C12 C13 C18 -175.8(3) . . . . ?
C11 C12 C13 C14 4.3(3) . . . . ?
C9 C10 C14 C13 -179.2(3) . . . . ?
C11 C10 C14 C13 -1.2(3) . . . . ?
C9 C10 C14 C15 -0.4(4) . . . . ?
C11 C10 C14 C15 177.5(3) . . . . ?
C18 C13 C14 C10 178.1(3) . . . . ?
C12 C13 C14 C10 -2.0(4) . . . . ?
C18 C13 C14 C15 -0.7(5) . . . . ?
C12 C13 C14 C15 179.2(3) . . . . ?
C1 N1 C15 C14 -0.9(4) . . . . ?
C1 N1 C15 C16 177.8(3) . . . . ?
C10 C14 C15 N1 1.0(4) . . . . ?
C13 C14 C15 N1 179.6(3) . . . . ?
C10 C14 C15 C16 -177.8(3) . . . . ?
C13 C14 C15 C16 0.8(4) . . . . ?
N1 C15 C16 C17 -178.9(3) . . . . ?
C14 C15 C16 C17 -0.1(5) . . . . ?
C15 C16 C17 C18 -0.6(5) . . . . ?
C14 C13 C18 C17 0.0(5) . . . . ?
C12 C13 C18 C17 -179.9(3) . . . . ?
C16 C17 C18 C13 0.7(6) . . . . ?
C33 N3 C19 C27 0.0(5) . . . . ?
C33 N3 C19 C20 178.6(3) . . . . ?
N3 C19 C20 C25 -178.5(3) . . . . ?
C27 C19 C20 C25 0.4(3) . . . . ?
N3 C19 C20 C21 2.5(5) . . . . ?
C27 C19 C20 C21 -178.6(3) . . . . ?
C25 C20 C21 N4 179.8(3) . . . . ?
C19 C20 C21 N4 -1.4(5) . . . . ?
C25 C20 C21 C22 1.3(5) . . . . ?
C19 C20 C21 C22 -179.8(3) . . . . ?
N4 C21 C22 C23 -179.1(3) . . . . ?
C20 C21 C22 C23 -0.7(5) . . . . ?
C21 C22 C23 C24 -0.2(6) . . . . ?
C22 C23 C24 C25 0.5(5) . . . . ?
C21 C20 C25 C24 -1.1(5) . . . . ?
C19 C20 C25 C24 179.9(3) . . . . ?
C21 C20 C25 C26 178.7(3) . . . . ?
C19 C20 C25 C26 -0.3(4) . . . . ?
C23 C24 C25 C20 0.2(5) . . . . ?
C23 C24 C25 C26 -179.6(3) . . . . ?
C20 C25 C26 C27 0.1(4) . . . . ?
C24 C25 C26 C27 179.9(3) . . . . ?
N3 C19 C27 C28 -0.8(5) . . . . ?
C20 C19 C27 C28 -179.5(2) . . . . ?
N3 C19 C27 C26 178.5(3) . . . . ?
C20 C19 C27 C26 -0.3(3) . . . . ?
C25 C26 C27 C28 179.2(3) . . . . ?
C25 C26 C27 C19 0.1(3) . . . . ?
C19 C27 C28 C32 0.7(4) . . . . ?
C26 C27 C28 C32 -178.3(3) . . . . ?
C19 C27 C28 C29 179.5(3) . . . . ?
C26 C27 C28 C29 0.5(6) . . . . ?
C27 C28 C29 C30 -178.8(3) . . . . ?
C32 C28 C29 C30 0.0(3) . . . . ?
C28 C29 C30 C31 0.5(3) . . . . ?
C29 C30 C31 C36 178.6(4) . . . . ?
C29 C30 C31 C32 -0.8(4) . . . . ?
C27 C28 C32 C33 -0.1(4) . . . . ?
C29 C28 C32 C33 -179.2(3) . . . . ?
C27 C28 C32 C31 178.5(3) . . . . ?
C29 C28 C32 C31 -0.6(4) . . . . ?
C36 C31 C32 C33 0.0(5) . . . . ?
C30 C31 C32 C33 179.5(3) . . . . ?
C36 C31 C32 C28 -178.6(3) . . . . ?
C30 C31 C32 C28 0.9(4) . . . . ?
C28 C32 C33 N3 -0.7(5) . . . . ?
C31 C32 C33 N3 -179.1(3) . . . . ?
C28 C32 C33 C34 179.0(3) . . . . ?
C31 C32 C33 C34 0.6(5) . . . . ?
C19 N3 C33 C32 0.7(4) . . . . ?
C19 N3 C33 C34 -179.0(3) . . . . ?
C32 C33 C34 C35 -0.7(5) . . . . ?
N3 C33 C34 C35 179.0(3) . . . . ?
C33 C34 C35 C36 0.2(5) . . . . ?
C32 C31 C36 C35 -0.5(5) . . . . ?
C30 C31 C36 C35 -179.8(4) . . . . ?
C34 C35 C36 C31 0.4(6) . . . . ?

_refine_diff_density_max         1.001
_refine_diff_density_min         -0.477
_refine_diff_density_rms         0.076

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_h-m   P-1
_symmetry_int_tables_number      ?
_chemical_absolute_configuration ?

####################################################################### 
# 
# 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_tsnh2
_database_code_depnum_ccdc_archive 'CCDC 2012191'
loop_
_audit_author_name
_audit_author_address
CPIQNHTs
;Feng Chia University
Taiwan
;
_audit_update_record             
;
2020-06-25 deposited with the CCDC.	2020-09-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C25 H20 N2 O2 S'
_chemical_formula_sum            'C25 H20 N2 O2 S'
_chemical_melting_point          ?

_exptl_crystal_description       parallelepiped
_exptl_crystal_colour            colourless
_diffrn_ambient_temperature      150(2)
_chemical_formula_weight         412.49

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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.1962(10)
_cell_length_b                   9.1505(10)
_cell_length_c                   14.0898(19)
_cell_angle_alpha                82.486(4)
_cell_angle_beta                 87.536(5)
_cell_angle_gamma                68.336(4)
_cell_volume                     973.6(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    7979
_cell_measurement_theta_min      2.674
_cell_measurement_theta_max      27.069
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.407
_exptl_crystal_F_000             432
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.290
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    0.192
_shelx_estimated_absorpt_T_min   0.946
_shelx_estimated_absorpt_T_max   0.992
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8640
_exptl_absorpt_correction_T_max  0.9281
_exptl_absorpt_process_details   'SADABS V2012/1 (Bruker AXS Inc.)'
_exptl_absorpt_special_details   ?
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            17881
_diffrn_reflns_av_unetI/netI     0.0552
_diffrn_reflns_av_R_equivalents  0.0565
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.674
_diffrn_reflns_theta_max         27.109
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.956
_diffrn_measured_fraction_theta_full 0.962
_diffrn_reflns_Laue_measured_fraction_max 0.956
_diffrn_reflns_Laue_measured_fraction_full 0.962
_diffrn_reflns_point_group_measured_fraction_max 0.956
_diffrn_reflns_point_group_measured_fraction_full 0.962
_reflns_number_total             4127
_reflns_number_gt                3173
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'APEX2 (Bruker AXS, 2010)'
_computing_cell_refinement       'SAINT V7.34A (Bruker AXS, 2006)'
_computing_data_reduction        'SAINT V7.34A (Bruker AXS, 2006)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0299P)²+1.5839P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4127
_refine_ls_number_parameters     275
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0731
_refine_ls_R_factor_gt           0.0515
_refine_ls_wR_factor_ref         0.1345
_refine_ls_wR_factor_gt          0.1266
_refine_ls_goodness_of_fit_ref   1.113
_refine_ls_restrained_S_all      1.113
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S S 0.04397(8) 0.82598(8) 0.32664(5) 0.01660(17) Uani 1 1 d . . . . .
O1 O -0.0858(2) 0.9170(2) 0.38892(13) 0.0233(4) Uani 1 1 d . . . . .
O2 O 0.0310(3) 0.6865(2) 0.29752(13) 0.0248(4) Uani 1 1 d . . . . .
N1 N 0.0426(3) 0.9388(3) 0.22697(16) 0.0182(5) Uani 1 1 d . . . . .
H1A H 0.084(4) 0.882(4) 0.181(3) 0.039(10) Uiso 1 1 d . . . . .
N2 N 0.2083(3) 0.8981(2) 0.04824(15) 0.0156(4) Uani 1 1 d . . . . .
C1 C 0.2502(3) 0.7737(3) 0.38099(18) 0.0165(5) Uani 1 1 d . . . . .
C2 C 0.2701(4) 0.8556(3) 0.45309(19) 0.0234(6) Uani 1 1 d . . . . .
H2C H 0.1729 0.9402 0.4737 0.028 Uiso 1 1 calc R U . . .
C3 C 0.4346(4) 0.8118(4) 0.4946(2) 0.0311(7) Uani 1 1 d . . . . .
H3A H 0.4489 0.8675 0.5440 0.037 Uiso 1 1 calc R U . . .
C4 C 0.5786(4) 0.6883(4) 0.4657(2) 0.0316(7) Uani 1 1 d . . . . .
C5 C 0.5551(4) 0.6082(4) 0.3937(2) 0.0312(7) Uani 1 1 d . . . . .
H5A H 0.6524 0.5233 0.3734 0.037 Uiso 1 1 calc R U . . .
C6 C 0.3927(4) 0.6493(3) 0.3505(2) 0.0241(6) Uani 1 1 d . . . . .
H6A H 0.3787 0.5937 0.3010 0.029 Uiso 1 1 calc R U . . .
C7 C 0.7561(4) 0.6429(5) 0.5121(3) 0.0510(11) Uani 1 1 d . . . . .
H7A H 0.7474 0.7122 0.5611 0.076 Uiso 1 1 calc R U . . .
H7B H 0.7952 0.5325 0.5418 0.076 Uiso 1 1 calc R U . . .
H7C H 0.8409 0.6547 0.4634 0.076 Uiso 1 1 calc R U . . .
C8 C 0.0556(3) 1.0898(3) 0.21827(18) 0.0161(5) Uani 1 1 d . . . . .
C9 C 0.0002(3) 1.1961(3) 0.28585(19) 0.0208(6) Uani 1 1 d . . . . .
H9A H -0.0486 1.1685 0.3447 0.025 Uiso 1 1 calc R U . . .
C10 C 0.0165(3) 1.3432(3) 0.2667(2) 0.0224(6) Uani 1 1 d . . . . .
H10A H -0.0208 1.4144 0.3136 0.027 Uiso 1 1 calc R U . . .
C11 C 0.0857(3) 1.3897(3) 0.1812(2) 0.0207(6) Uani 1 1 d . . . . .
H11A H 0.0951 1.4909 0.1695 0.025 Uiso 1 1 calc R U . . .
C12 C 0.1404(3) 1.2845(3) 0.11390(19) 0.0181(5) Uani 1 1 d . . . . .
C13 C 0.2216(3) 1.3020(3) 0.01655(19) 0.0191(5) Uani 1 1 d . . . . .
H13A H 0.1400 1.3907 -0.0265 0.023 Uiso 1 1 calc R U . . .
H13B H 0.3327 1.3199 0.0220 0.023 Uiso 1 1 calc R U . . .
C14 C 0.2544(3) 1.1448(3) -0.01888(18) 0.0163(5) Uani 1 1 d . . . . .
C15 C 0.3249(3) 1.0825(3) -0.10060(18) 0.0177(5) Uani 1 1 d . . . . .
C16 C 0.3975(4) 1.1436(3) -0.19097(19) 0.0220(6) Uani 1 1 d . . . . .
H16A H 0.4989 1.1710 -0.1763 0.026 Uiso 1 1 calc R U . . .
H16B H 0.3065 1.2386 -0.2245 0.026 Uiso 1 1 calc R U . . .
C17 C 0.4553(4) 1.0035(3) -0.25323(19) 0.0227(6) Uani 1 1 d . . . . .
H17A H 0.3892 1.0353 -0.3144 0.027 Uiso 1 1 calc R U . . .
H17B H 0.5824 0.9691 -0.2673 0.027 Uiso 1 1 calc R U . . .
C18 C 0.4135(3) 0.8722(3) -0.19294(19) 0.0197(6) Uani 1 1 d . . . . .
C19 C 0.4350(4) 0.7205(3) -0.2070(2) 0.0246(6) Uani 1 1 d . . . . .
H19A H 0.4853 0.6798 -0.2645 0.030 Uiso 1 1 calc R U . . .
C20 C 0.3811(4) 0.6258(3) -0.1345(2) 0.0256(6) Uani 1 1 d . . . . .
H20A H 0.3971 0.5207 -0.1444 0.031 Uiso 1 1 calc R U . . .
C21 C 0.3065(3) 0.6796(3) -0.05043(19) 0.0198(5) Uani 1 1 d . . . . .
H21A H 0.2716 0.6124 -0.0036 0.024 Uiso 1 1 calc R U . . .
C22 C 0.2819(3) 0.8352(3) -0.03393(18) 0.0158(5) Uani 1 1 d . . . . .
C23 C 0.3384(3) 0.9263(3) -0.10662(18) 0.0168(5) Uani 1 1 d . . . . .
C24 C 0.1976(3) 1.0462(3) 0.05215(18) 0.0151(5) Uani 1 1 d . . . . .
C25 C 0.1267(3) 1.1354(3) 0.13270(18) 0.0157(5) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S O2 1.4314(19) . ?
S O1 1.4323(19) . ?
S N1 1.628(2) . ?
S C1 1.758(3) . ?
N1 C8 1.414(3) . ?
N1 H1A 0.86(4) . ?
N2 C24 1.334(3) . ?
N2 C22 1.376(3) . ?
C1 C6 1.396(4) . ?
C1 C2 1.387(4) . ?
C2 C3 1.388(4) . ?
C2 H2C 0.9500 . ?
C3 C4 1.389(5) . ?
C3 H3A 0.9500 . ?
C4 C5 1.386(5) . ?
C4 C7 1.510(4) . ?
C5 C6 1.387(4) . ?
C5 H5A 0.9500 . ?
C6 H6A 0.9500 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 C25 1.398(4) . ?
C8 C9 1.393(4) . ?
C9 C10 1.392(4) . ?
C9 H9A 0.9500 . ?
C10 C11 1.392(4) . ?
C10 H10A 0.9500 . ?
C11 C12 1.382(4) . ?
C11 H11A 0.9500 . ?
C12 C25 1.401(3) . ?
C12 C13 1.514(4) . ?
C13 C14 1.511(3) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.362(4) . ?
C14 C24 1.437(3) . ?
C15 C23 1.405(4) . ?
C15 C16 1.511(4) . ?
C16 C17 1.564(4) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 C18 1.515(4) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 C19 1.373(4) . ?
C18 C23 1.404(4) . ?
C19 C20 1.414(4) . ?
C19 H19A 0.9500 . ?
C20 C21 1.374(4) . ?
C20 H20A 0.9500 . ?
C21 C22 1.412(4) . ?
C21 H21A 0.9500 . ?
C22 C23 1.407(4) . ?
C24 C25 1.458(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 S O1 119.75(12) . . ?
O2 S N1 104.64(11) . . ?
O1 S N1 108.51(12) . . ?
O2 S C1 108.46(12) . . ?
O1 S C1 107.55(12) . . ?
N1 S C1 107.35(12) . . ?
C8 N1 S 126.07(18) . . ?
C8 N1 H1A 117(2) . . ?
S N1 H1A 110(2) . . ?
C24 N2 C22 115.1(2) . . ?
C6 C1 C2 120.7(3) . . ?
C6 C1 S 119.1(2) . . ?
C2 C1 S 120.2(2) . . ?
C1 C2 C3 118.9(3) . . ?
C1 C2 H2C 120.6 . . ?
C3 C2 H2C 120.6 . . ?
C4 C3 C2 121.6(3) . . ?
C4 C3 H3A 119.2 . . ?
C2 C3 H3A 119.2 . . ?
C5 C4 C3 118.4(3) . . ?
C5 C4 C7 121.0(3) . . ?
C3 C4 C7 120.5(3) . . ?
C6 C5 C4 121.4(3) . . ?
C6 C5 H5A 119.3 . . ?
C4 C5 H5A 119.3 . . ?
C5 C6 C1 119.0(3) . . ?
C5 C6 H6A 120.5 . . ?
C1 C6 H6A 120.5 . . ?
C4 C7 H7A 109.5 . . ?
C4 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C4 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C25 C8 C9 118.2(2) . . ?
C25 C8 N1 116.0(2) . . ?
C9 C8 N1 125.7(2) . . ?
C10 C9 C8 119.7(2) . . ?
C10 C9 H9A 120.2 . . ?
C8 C9 H9A 120.2 . . ?
C9 C10 C11 122.3(2) . . ?
C9 C10 H10A 118.9 . . ?
C11 C10 H10A 118.9 . . ?
C12 C11 C10 118.2(2) . . ?
C12 C11 H11A 120.9 . . ?
C10 C11 H11A 120.9 . . ?
C25 C12 C11 120.1(2) . . ?
C25 C12 C13 110.2(2) . . ?
C11 C12 C13 129.6(2) . . ?
C14 C13 C12 103.0(2) . . ?
C14 C13 H13A 111.2 . . ?
C12 C13 H13A 111.2 . . ?
C14 C13 H13B 111.2 . . ?
C12 C13 H13B 111.2 . . ?
H13A C13 H13B 109.1 . . ?
C15 C14 C24 117.1(2) . . ?
C15 C14 C13 133.4(2) . . ?
C24 C14 C13 109.5(2) . . ?
C14 C15 C23 116.8(2) . . ?
C14 C15 C16 134.2(2) . . ?
C23 C15 C16 109.0(2) . . ?
C15 C16 C17 104.7(2) . . ?
C15 C16 H16A 110.8 . . ?
C17 C16 H16A 110.8 . . ?
C15 C16 H16B 110.8 . . ?
C17 C16 H16B 110.8 . . ?
H16A C16 H16B 108.9 . . ?
C18 C17 C16 104.9(2) . . ?
C18 C17 H17A 110.8 . . ?
C16 C17 H17A 110.8 . . ?
C18 C17 H17B 110.8 . . ?
C16 C17 H17B 110.8 . . ?
H17A C17 H17B 108.8 . . ?
C19 C18 C23 118.1(2) . . ?
C19 C18 C17 133.2(3) . . ?
C23 C18 C17 108.7(2) . . ?
C18 C19 C20 119.0(3) . . ?
C18 C19 H19A 120.5 . . ?
C20 C19 H19A 120.5 . . ?
C21 C20 C19 122.7(3) . . ?
C21 C20 H20A 118.7 . . ?
C19 C20 H20A 118.7 . . ?
C20 C21 C22 119.7(3) . . ?
C20 C21 H21A 120.1 . . ?
C22 C21 H21A 120.1 . . ?
N2 C22 C23 120.2(2) . . ?
N2 C22 C21 123.3(2) . . ?
C23 C22 C21 116.5(2) . . ?
C22 C23 C18 124.0(2) . . ?
C22 C23 C15 123.4(2) . . ?
C18 C23 C15 112.6(2) . . ?
N2 C24 C14 127.4(2) . . ?
N2 C24 C25 124.6(2) . . ?
C14 C24 C25 108.0(2) . . ?
C12 C25 C8 121.5(2) . . ?
C12 C25 C24 109.3(2) . . ?
C8 C25 C24 129.2(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 S N1 C8 -178.9(2) . . . . ?
O1 S N1 C8 52.1(2) . . . . ?
C1 S N1 C8 -63.8(2) . . . . ?
O2 S C1 C6 30.9(2) . . . . ?
O1 S C1 C6 161.7(2) . . . . ?
N1 S C1 C6 -81.7(2) . . . . ?
O2 S C1 C2 -149.2(2) . . . . ?
O1 S C1 C2 -18.3(2) . . . . ?
N1 S C1 C2 98.3(2) . . . . ?
C6 C1 C2 C3 0.0(4) . . . . ?
S C1 C2 C3 -179.9(2) . . . . ?
C1 C2 C3 C4 -0.1(4) . . . . ?
C2 C3 C4 C5 0.0(4) . . . . ?
C2 C3 C4 C7 180.0(3) . . . . ?
C3 C4 C5 C6 0.2(4) . . . . ?
C7 C4 C5 C6 -179.8(3) . . . . ?
C4 C5 C6 C1 -0.3(4) . . . . ?
C2 C1 C6 C5 0.2(4) . . . . ?
S C1 C6 C5 -179.9(2) . . . . ?
S N1 C8 C25 153.18(19) . . . . ?
S N1 C8 C9 -28.6(4) . . . . ?
C25 C8 C9 C10 0.0(4) . . . . ?
N1 C8 C9 C10 -178.2(2) . . . . ?
C8 C9 C10 C11 0.6(4) . . . . ?
C9 C10 C11 C12 -0.4(4) . . . . ?
C10 C11 C12 C25 -0.4(4) . . . . ?
C10 C11 C12 C13 -179.2(2) . . . . ?
C25 C12 C13 C14 -0.3(3) . . . . ?
C11 C12 C13 C14 178.6(3) . . . . ?
C12 C13 C14 C15 -179.7(3) . . . . ?
C12 C13 C14 C24 -0.2(3) . . . . ?
C24 C14 C15 C23 -1.2(3) . . . . ?
C13 C14 C15 C23 178.2(2) . . . . ?
C24 C14 C15 C16 179.4(3) . . . . ?
C13 C14 C15 C16 -1.2(5) . . . . ?
C14 C15 C16 C17 179.9(3) . . . . ?
C23 C15 C16 C17 0.6(3) . . . . ?
C15 C16 C17 C18 -0.8(3) . . . . ?
C16 C17 C18 C19 -179.2(3) . . . . ?
C16 C17 C18 C23 0.7(3) . . . . ?
C23 C18 C19 C20 0.0(4) . . . . ?
C17 C18 C19 C20 179.9(3) . . . . ?
C18 C19 C20 C21 0.5(4) . . . . ?
C19 C20 C21 C22 -0.2(4) . . . . ?
C24 N2 C22 C23 -0.4(3) . . . . ?
C24 N2 C22 C21 179.1(2) . . . . ?
C20 C21 C22 N2 -180.0(2) . . . . ?
C20 C21 C22 C23 -0.5(4) . . . . ?
N2 C22 C23 C18 -179.5(2) . . . . ?
C21 C22 C23 C18 1.0(4) . . . . ?
N2 C22 C23 C15 0.2(4) . . . . ?
C21 C22 C23 C15 -179.3(2) . . . . ?
C19 C18 C23 C22 -0.8(4) . . . . ?
C17 C18 C23 C22 179.3(2) . . . . ?
C19 C18 C23 C15 179.5(2) . . . . ?
C17 C18 C23 C15 -0.4(3) . . . . ?
C14 C15 C23 C22 0.6(4) . . . . ?
C16 C15 C23 C22 -179.8(2) . . . . ?
C14 C15 C23 C18 -179.6(2) . . . . ?
C16 C15 C23 C18 -0.1(3) . . . . ?
C22 N2 C24 C14 -0.3(3) . . . . ?
C22 N2 C24 C25 -179.1(2) . . . . ?
C15 C14 C24 N2 1.2(4) . . . . ?
C13 C14 C24 N2 -178.4(2) . . . . ?
C15 C14 C24 C25 -179.8(2) . . . . ?
C13 C14 C24 C25 0.6(3) . . . . ?
C11 C12 C25 C8 1.0(4) . . . . ?
C13 C12 C25 C8 -180.0(2) . . . . ?
C11 C12 C25 C24 -178.3(2) . . . . ?
C13 C12 C25 C24 0.7(3) . . . . ?
C9 C8 C25 C12 -0.8(4) . . . . ?
N1 C8 C25 C12 177.6(2) . . . . ?
C9 C8 C25 C24 178.4(2) . . . . ?
N1 C8 C25 C24 -3.2(4) . . . . ?
N2 C24 C25 C12 178.2(2) . . . . ?
C14 C24 C25 C12 -0.8(3) . . . . ?
N2 C24 C25 C8 -1.1(4) . . . . ?
C14 C24 C25 C8 179.9(2) . . . . ?

_refine_diff_density_max         0.388
_refine_diff_density_min         -0.500
_refine_diff_density_rms         0.071

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_h-m   P-1
_symmetry_int_tables_number      ?
_chemical_absolute_configuration ?

####################################################################### 
# 
# 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_nh2nh2_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2012189'
loop_
_audit_author_name
_audit_author_address
CPIQNHMe
;Feng Chia University
Taiwan
;
_audit_update_record             
;
2020-06-25 deposited with the CCDC.	2020-09-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H16 N2'
_chemical_formula_weight         272.34

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'

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

_shelx_space_group_comment       
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;

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

_cell_length_a                   6.9216(4)
_cell_length_b                   15.8745(9)
_cell_length_c                   12.8437(8)
_cell_angle_alpha                90
_cell_angle_beta                 103.530(3)
_cell_angle_gamma                90
_cell_volume                     1372.06(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9944
_cell_measurement_theta_min      3.041
_cell_measurement_theta_max      27.095

_exptl_crystal_description       parallelepiped
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.318
_exptl_crystal_F_000             576
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.430
_exptl_crystal_size_mid          0.420
_exptl_crystal_size_min          0.260
_exptl_absorpt_coefficient_mu    0.078
_shelx_estimated_absorpt_T_min   0.967
_shelx_estimated_absorpt_T_max   0.980
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8825
_exptl_absorpt_correction_T_max  0.9281
_exptl_absorpt_process_details   'SADABS V2012/1 (Bruker AXS Inc.)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            25175
_diffrn_reflns_av_unetI/netI     0.0217
_diffrn_reflns_av_R_equivalents  0.0424
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.263
_diffrn_reflns_theta_max         27.107
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             3004
_reflns_number_gt                2619
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'APEX2 (Bruker AXS, 2010)'
_computing_cell_refinement       'SAINT V7.34A (Bruker AXS, 2006)'
_computing_data_reduction        'SAINT V7.34A (Bruker AXS, 2006)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0705P)²+0.4225P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3004
_refine_ls_number_parameters     194
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0460
_refine_ls_R_factor_gt           0.0394
_refine_ls_wR_factor_ref         0.1193
_refine_ls_wR_factor_gt          0.1100
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_restrained_S_all      1.011
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.27800(13) 0.36078(6) 0.68592(7) 0.0217(2) Uani 1 1 d . . . . .
N2 N -0.05138(16) 0.24855(7) 0.69949(8) 0.0287(2) Uani 1 1 d . . . . .
H2A H 0.020(2) 0.2928(11) 0.7273(13) 0.037(4) Uiso 1 1 d . . . . .
C1 C 0.56053(15) 0.42904(7) 0.64138(9) 0.0217(2) Uani 1 1 d . . . . .
C2 C 0.42156(15) 0.42289(7) 0.70523(8) 0.0213(2) Uani 1 1 d . . . . .
C3 C 0.43661(17) 0.48420(7) 0.78701(9) 0.0263(3) Uani 1 1 d . . . . .
H3A H 0.3466 0.4833 0.8326 0.032 Uiso 1 1 calc R U . . .
C4 C 0.58276(18) 0.54534(8) 0.80012(10) 0.0292(3) Uani 1 1 d . . . . .
H4A H 0.5906 0.5860 0.8552 0.035 Uiso 1 1 calc R U . . .
C5 C 0.72118(17) 0.54975(8) 0.73464(10) 0.0288(3) Uani 1 1 d . . . . .
H5A H 0.8199 0.5925 0.7455 0.035 Uiso 1 1 calc R U . . .
C6 C 0.70961(16) 0.49088(7) 0.65510(9) 0.0251(3) Uani 1 1 d . . . . .
C7 C 0.82958(17) 0.47753(8) 0.57190(10) 0.0300(3) Uani 1 1 d . . . . .
H7A H 0.9695 0.4641 0.6066 0.036 Uiso 1 1 calc R U . . .
H7B H 0.8267 0.5286 0.5273 0.036 Uiso 1 1 calc R U . . .
C8 C 0.72803(17) 0.40194(8) 0.50237(10) 0.0276(3) Uani 1 1 d . . . . .
H8A H 0.6746 0.4196 0.4272 0.033 Uiso 1 1 calc R U . . .
H8B H 0.8236 0.3553 0.5037 0.033 Uiso 1 1 calc R U . . .
C9 C 0.56132(16) 0.37511(7) 0.55383(8) 0.0224(2) Uani 1 1 d . . . . .
C10 C 0.41772(16) 0.31447(7) 0.53339(8) 0.0224(2) Uani 1 1 d . . . . .
C11 C 0.36553(18) 0.24689(7) 0.44892(9) 0.0269(3) Uani 1 1 d . . . . .
H11A H 0.4779 0.2075 0.4526 0.032 Uiso 1 1 calc R U . . .
H11B H 0.3276 0.2717 0.3763 0.032 Uiso 1 1 calc R U . . .
C12 C 0.19030(17) 0.20293(7) 0.47768(9) 0.0256(3) Uani 1 1 d . . . . .
C13 C 0.08113(19) 0.13447(7) 0.42796(10) 0.0312(3) Uani 1 1 d . . . . .
H13A H 0.1122 0.1082 0.3674 0.037 Uiso 1 1 calc R U . . .
C14 C -0.0752(2) 0.10555(8) 0.46967(10) 0.0342(3) Uani 1 1 d . . . . .
H14A H -0.1519 0.0592 0.4362 0.041 Uiso 1 1 calc R U . . .
C15 C -0.12266(18) 0.14227(8) 0.55861(10) 0.0300(3) Uani 1 1 d . . . . .
H15A H -0.2304 0.1206 0.5846 0.036 Uiso 1 1 calc R U . . .
C16 C -0.01321(16) 0.21136(7) 0.61090(9) 0.0237(2) Uani 1 1 d . . . . .
C17 C 0.14447(16) 0.24092(7) 0.56734(9) 0.0222(2) Uani 1 1 d . . . . .
C18 C 0.28175(15) 0.31056(7) 0.60351(8) 0.0205(2) Uani 1 1 d . . . . .
C19 C -0.20183(19) 0.21855(9) 0.75188(10) 0.0331(3) Uani 1 1 d . . . . .
H19A H -0.2039 0.2545 0.8137 0.050 Uiso 1 1 calc R U . . .
H19B H -0.3321 0.2204 0.7014 0.050 Uiso 1 1 calc R U . . .
H19C H -0.1715 0.1605 0.7761 0.050 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C18 1.3302(14) . ?
N1 C2 1.3804(14) . ?
N2 C16 1.3614(16) . ?
N2 C19 1.4464(15) . ?
N2 H2A 0.884(17) . ?
C1 C6 1.4050(16) . ?
C1 C2 1.4059(15) . ?
C1 C9 1.4144(16) . ?
C2 C3 1.4178(15) . ?
C3 C4 1.3834(17) . ?
C3 H3A 0.9500 . ?
C4 C5 1.4167(17) . ?
C4 H4A 0.9500 . ?
C5 C6 1.3730(17) . ?
C5 H5A 0.9500 . ?
C6 C7 1.5138(16) . ?
C7 C8 1.5614(18) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.5187(15) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.3643(16) . ?
C10 C18 1.4482(14) . ?
C10 C11 1.5083(16) . ?
C11 C12 1.5179(17) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.3908(17) . ?
C12 C17 1.4005(16) . ?
C13 C14 1.3926(19) . ?
C13 H13A 0.9500 . ?
C14 C15 1.3887(19) . ?
C14 H14A 0.9500 . ?
C15 C16 1.4106(16) . ?
C15 H15A 0.9500 . ?
C16 C17 1.4178(16) . ?
C17 C18 1.4608(15) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 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
C18 N1 C2 115.08(9) . . ?
C16 N2 C19 123.20(11) . . ?
C16 N2 H2A 119.0(10) . . ?
C19 N2 H2A 117.8(10) . . ?
C6 C1 C2 123.92(11) . . ?
C6 C1 C9 112.54(10) . . ?
C2 C1 C9 123.51(10) . . ?
N1 C2 C1 120.45(10) . . ?
N1 C2 C3 123.26(10) . . ?
C1 C2 C3 116.28(10) . . ?
C4 C3 C2 119.78(11) . . ?
C4 C3 H3A 120.1 . . ?
C2 C3 H3A 120.1 . . ?
C3 C4 C5 122.63(11) . . ?
C3 C4 H4A 118.7 . . ?
C5 C4 H4A 118.7 . . ?
C6 C5 C4 118.57(11) . . ?
C6 C5 H5A 120.7 . . ?
C4 C5 H5A 120.7 . . ?
C5 C6 C1 118.83(11) . . ?
C5 C6 C7 132.40(11) . . ?
C1 C6 C7 108.77(10) . . ?
C6 C7 C8 105.28(9) . . ?
C6 C7 H7A 110.7 . . ?
C8 C7 H7A 110.7 . . ?
C6 C7 H7B 110.7 . . ?
C8 C7 H7B 110.7 . . ?
H7A C7 H7B 108.8 . . ?
C9 C8 C7 104.64(9) . . ?
C9 C8 H8A 110.8 . . ?
C7 C8 H8A 110.8 . . ?
C9 C8 H8B 110.8 . . ?
C7 C8 H8B 110.8 . . ?
H8A C8 H8B 108.9 . . ?
C10 C9 C1 116.22(10) . . ?
C10 C9 C8 135.05(10) . . ?
C1 C9 C8 108.72(10) . . ?
C9 C10 C18 117.44(10) . . ?
C9 C10 C11 132.95(10) . . ?
C18 C10 C11 109.61(10) . . ?
C10 C11 C12 102.86(9) . . ?
C10 C11 H11A 111.2 . . ?
C12 C11 H11A 111.2 . . ?
C10 C11 H11B 111.2 . . ?
C12 C11 H11B 111.2 . . ?
H11A C11 H11B 109.1 . . ?
C13 C12 C17 120.72(11) . . ?
C13 C12 C11 128.81(11) . . ?
C17 C12 C11 110.47(10) . . ?
C12 C13 C14 117.93(12) . . ?
C12 C13 H13A 121.0 . . ?
C14 C13 H13A 121.0 . . ?
C15 C14 C13 122.19(11) . . ?
C15 C14 H14A 118.9 . . ?
C13 C14 H14A 118.9 . . ?
C14 C15 C16 120.93(12) . . ?
C14 C15 H15A 119.5 . . ?
C16 C15 H15A 119.5 . . ?
N2 C16 C15 123.19(11) . . ?
N2 C16 C17 120.27(10) . . ?
C15 C16 C17 116.53(11) . . ?
C12 C17 C16 121.69(10) . . ?
C12 C17 C18 109.37(10) . . ?
C16 C17 C18 128.94(10) . . ?
N1 C18 C10 127.27(10) . . ?
N1 C18 C17 125.05(10) . . ?
C10 C18 C17 107.68(9) . . ?
N2 C19 H19A 109.5 . . ?
N2 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
N2 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 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
C18 N1 C2 C1 -1.09(14) . . . . ?
C18 N1 C2 C3 177.65(10) . . . . ?
C6 C1 C2 N1 179.29(10) . . . . ?
C9 C1 C2 N1 1.43(16) . . . . ?
C6 C1 C2 C3 0.47(16) . . . . ?
C9 C1 C2 C3 -177.40(10) . . . . ?
N1 C2 C3 C4 -178.90(10) . . . . ?
C1 C2 C3 C4 -0.11(16) . . . . ?
C2 C3 C4 C5 -0.08(18) . . . . ?
C3 C4 C5 C6 -0.06(18) . . . . ?
C4 C5 C6 C1 0.39(16) . . . . ?
C4 C5 C6 C7 179.50(11) . . . . ?
C2 C1 C6 C5 -0.62(17) . . . . ?
C9 C1 C6 C5 177.45(10) . . . . ?
C2 C1 C6 C7 -179.92(10) . . . . ?
C9 C1 C6 C7 -1.85(13) . . . . ?
C5 C6 C7 C8 -176.69(12) . . . . ?
C1 C6 C7 C8 2.49(12) . . . . ?
C6 C7 C8 C9 -2.18(11) . . . . ?
C6 C1 C9 C10 -178.45(9) . . . . ?
C2 C1 C9 C10 -0.37(16) . . . . ?
C6 C1 C9 C8 0.37(13) . . . . ?
C2 C1 C9 C8 178.45(9) . . . . ?
C7 C8 C9 C10 179.69(12) . . . . ?
C7 C8 C9 C1 1.20(12) . . . . ?
C1 C9 C10 C18 -0.84(14) . . . . ?
C8 C9 C10 C18 -179.25(11) . . . . ?
C1 C9 C10 C11 178.89(11) . . . . ?
C8 C9 C10 C11 0.5(2) . . . . ?
C9 C10 C11 C12 179.33(11) . . . . ?
C18 C10 C11 C12 -0.93(11) . . . . ?
C10 C11 C12 C13 -179.23(11) . . . . ?
C10 C11 C12 C17 0.61(12) . . . . ?
C17 C12 C13 C14 0.43(17) . . . . ?
C11 C12 C13 C14 -179.75(11) . . . . ?
C12 C13 C14 C15 -0.56(18) . . . . ?
C13 C14 C15 C16 0.09(19) . . . . ?
C19 N2 C16 C15 3.00(18) . . . . ?
C19 N2 C16 C17 -176.18(10) . . . . ?
C14 C15 C16 N2 -178.72(11) . . . . ?
C14 C15 C16 C17 0.49(17) . . . . ?
C13 C12 C17 C16 0.16(17) . . . . ?
C11 C12 C17 C16 -179.69(10) . . . . ?
C13 C12 C17 C18 179.78(10) . . . . ?
C11 C12 C17 C18 -0.07(12) . . . . ?
N2 C16 C17 C12 178.62(10) . . . . ?
C15 C16 C17 C12 -0.61(16) . . . . ?
N2 C16 C17 C18 -0.92(18) . . . . ?
C15 C16 C17 C18 179.85(10) . . . . ?
C2 N1 C18 C10 -0.18(16) . . . . ?
C2 N1 C18 C17 -179.61(9) . . . . ?
C9 C10 C18 N1 1.20(16) . . . . ?
C11 C10 C18 N1 -178.59(10) . . . . ?
C9 C10 C18 C17 -179.29(9) . . . . ?
C11 C10 C18 C17 0.92(12) . . . . ?
C12 C17 C18 N1 179.00(10) . . . . ?
C16 C17 C18 N1 -1.42(18) . . . . ?
C12 C17 C18 C10 -0.53(12) . . . . ?
C16 C17 C18 C10 179.06(10) . . . . ?

_refine_diff_density_max         0.277
_refine_diff_density_min         -0.229
_refine_diff_density_rms         0.045

####################################################################### 
# 
# 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_nhacnh2
_database_code_depnum_ccdc_archive 'CCDC 2012190'
loop_
_audit_author_name
_audit_author_address
CPIQNHAc
;Feng Chia University
Taiwan
;
_audit_update_record             
;
2020-06-25 deposited with the CCDC.	2020-09-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C20 H16 N2 O'
_chemical_formula_sum            'C20 H16 N2 O'
_chemical_melting_point          ?

_exptl_crystal_description       parallelepiped
_exptl_crystal_colour            yellow
_diffrn_ambient_temperature      150(2)
_chemical_formula_weight         300.35

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'

_shelx_space_group_comment       
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;

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

_cell_length_a                   18.6355(8)
_cell_length_b                   7.0763(2)
_cell_length_c                   22.0296(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2905.05(19)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9909
_cell_measurement_theta_min      2.863
_cell_measurement_theta_max      27.064
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.373
_exptl_crystal_F_000             1264
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.600
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.090
_exptl_absorpt_coefficient_mu    0.086
_shelx_estimated_absorpt_T_min   0.950
_shelx_estimated_absorpt_T_max   0.992
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8598
_exptl_absorpt_correction_T_max  0.9281
_exptl_absorpt_process_details   'SADABS V2012/1 (Bruker AXS Inc.)'
_exptl_absorpt_special_details   ?
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            33227
_diffrn_reflns_av_unetI/netI     0.0345
_diffrn_reflns_av_R_equivalents  0.0413
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         2.863
_diffrn_reflns_theta_max         27.176
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             6405
_reflns_number_gt                5433
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.947
_reflns_Friedel_fraction_max     0.995
_reflns_Friedel_fraction_full    0.999

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'APEX2 (Bruker AXS, 2010)'
_computing_cell_refinement       'SAINT V7.34A (Bruker AXS, 2006)'
_computing_data_reduction        'SAINT V7.34A (Bruker AXS, 2006)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0672P)²+0.7323P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
; 
 Flack x determined using 2350 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.3(4)
_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_h-m   Pna2(1)
_symmetry_int_tables_number      ?
_chemical_absolute_configuration ?
_refine_ls_number_reflns         6405
_refine_ls_number_parameters     423
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0560
_refine_ls_R_factor_gt           0.0428
_refine_ls_wR_factor_ref         0.1147
_refine_ls_wR_factor_gt          0.1055
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_restrained_S_all      1.021
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.11329(12) 0.6623(3) 0.27694(9) 0.0316(5) Uani 1 1 d . . . . .
N1 N 0.12941(12) 0.8297(3) 0.05312(11) 0.0195(5) Uani 1 1 d . . . . .
N2 N 0.10799(13) 0.7500(3) 0.17714(12) 0.0216(5) Uani 1 1 d . . . . .
H2A H 0.1353(18) 0.773(5) 0.1435(17) 0.028(9) Uiso 1 1 d . . . . .
C1 C 0.16123(15) 0.8600(4) -0.00230(12) 0.0190(6) Uani 1 1 d . . . . .
C2 C 0.23648(15) 0.8735(4) -0.00993(14) 0.0242(6) Uani 1 1 d . . . . .
H2B H 0.2675 0.8627 0.0241 0.029 Uiso 1 1 calc R U . . .
C3 C 0.26445(16) 0.9026(4) -0.06740(13) 0.0253(6) Uani 1 1 d . . . . .
H3A H 0.3150 0.9113 -0.0720 0.030 Uiso 1 1 calc R U . . .
C4 C 0.22046(16) 0.9199(4) -0.11982(14) 0.0251(6) Uani 1 1 d . . . . .
H4B H 0.2413 0.9402 -0.1586 0.030 Uiso 1 1 calc R U . . .
C5 C 0.14743(16) 0.9066(4) -0.11333(13) 0.0227(6) Uani 1 1 d . . . . .
C6 C 0.08588(17) 0.9175(5) -0.15850(15) 0.0328(7) Uani 1 1 d . . . . .
H6A H 0.0897 0.8155 -0.1891 0.039 Uiso 1 1 calc R U . . .
H6B H 0.0857 1.0410 -0.1796 0.039 Uiso 1 1 calc R U . . .
C7 C 0.01669(17) 0.8929(4) -0.11915(14) 0.0271(6) Uani 1 1 d . . . . .
H7A H -0.0148 1.0049 -0.1229 0.032 Uiso 1 1 calc R U . . .
H7B H -0.0105 0.7795 -0.1320 0.032 Uiso 1 1 calc R U . . .
C8 C 0.04331(15) 0.8713(4) -0.05444(14) 0.0206(6) Uani 1 1 d . . . . .
C9 C 0.11911(15) 0.8783(4) -0.05489(13) 0.0195(6) Uani 1 1 d . . . . .
C10 C 0.01161(15) 0.8464(4) 0.00058(14) 0.0204(6) Uani 1 1 d . . . . .
C11 C -0.06564(16) 0.8336(4) 0.02078(14) 0.0233(6) Uani 1 1 d . . . . .
H11A H -0.0908 0.7289 0.0000 0.028 Uiso 1 1 calc R U . . .
H11B H -0.0915 0.9533 0.0128 0.028 Uiso 1 1 calc R U . . .
C12 C -0.05936(15) 0.7961(4) 0.08869(14) 0.0220(6) Uani 1 1 d . . . . .
C13 C -0.11235(17) 0.7690(4) 0.13187(15) 0.0269(6) Uani 1 1 d . . . . .
H13A H -0.1616 0.7754 0.1210 0.032 Uiso 1 1 calc R U . . .
C14 C -0.09208(16) 0.7322(4) 0.19167(14) 0.0276(7) Uani 1 1 d . . . . .
H14A H -0.1282 0.7122 0.2214 0.033 Uiso 1 1 calc R U . . .
C15 C -0.02010(16) 0.7241(4) 0.20895(14) 0.0250(6) Uani 1 1 d . . . . .
H15A H -0.0077 0.6985 0.2500 0.030 Uiso 1 1 calc R U . . .
C16 C 0.03361(15) 0.7536(4) 0.16571(13) 0.0201(6) Uani 1 1 d . . . . .
C17 C 0.01345(15) 0.7904(4) 0.10549(13) 0.0199(6) Uani 1 1 d . . . . .
C18 C 0.05808(14) 0.8233(4) 0.05214(13) 0.0181(5) Uani 1 1 d . . . . .
C19 C 0.14327(15) 0.7044(4) 0.22904(13) 0.0203(6) Uani 1 1 d . . . . .
C20 C 0.22380(16) 0.7071(4) 0.22281(14) 0.0242(6) Uani 1 1 d . . . . .
H20A H 0.2367 0.7440 0.1814 0.036 Uiso 1 1 calc R U . . .
H20B H 0.2441 0.7981 0.2516 0.036 Uiso 1 1 calc R U . . .
H20C H 0.2430 0.5809 0.2314 0.036 Uiso 1 1 calc R U . . .
O2 O 0.16245(12) 0.4013(3) -0.16520(10) 0.0342(5) Uani 1 1 d . . . . .
N3 N 0.17519(12) 0.3147(3) 0.06310(10) 0.0181(5) Uani 1 1 d . . . . .
N4 N 0.15598(13) 0.3810(3) -0.06198(11) 0.0213(5) Uani 1 1 d . . . . .
H4A H 0.180(2) 0.365(5) -0.0223(18) 0.042(10) Uiso 1 1 d . . . . .
C21 C 0.20568(15) 0.2768(4) 0.11840(13) 0.0191(6) Uani 1 1 d . . . . .
C22 C 0.28101(16) 0.2642(4) 0.12711(14) 0.0236(6) Uani 1 1 d . . . . .
H22A H 0.3129 0.2848 0.0941 0.028 Uiso 1 1 calc R U . . .
C23 C 0.30729(16) 0.2220(4) 0.18374(13) 0.0251(6) Uani 1 1 d . . . . .
H23A H 0.3578 0.2122 0.1889 0.030 Uiso 1 1 calc R U . . .
C24 C 0.26257(16) 0.1921(4) 0.23498(13) 0.0244(6) Uani 1 1 d . . . . .
H24A H 0.2826 0.1623 0.2735 0.029 Uiso 1 1 calc R U . . .
C25 C 0.18948(15) 0.2075(4) 0.22757(13) 0.0210(6) Uani 1 1 d . . . . .
C26 C 0.12648(16) 0.1866(4) 0.27116(13) 0.0252(6) Uani 1 1 d . . . . .
H26A H 0.1295 0.2810 0.3042 0.030 Uiso 1 1 calc R U . . .
H26B H 0.1257 0.0585 0.2893 0.030 Uiso 1 1 calc R U . . .
C27 C 0.05836(15) 0.2204(4) 0.23164(13) 0.0226(6) Uani 1 1 d . . . . .
H27A H 0.0266 0.1082 0.2324 0.027 Uiso 1 1 calc R U . . .
H27B H 0.0311 0.3312 0.2465 0.027 Uiso 1 1 calc R U . . .
C28 C 0.08683(14) 0.2557(4) 0.16785(13) 0.0184(6) Uani 1 1 d . . . . .
C29 C 0.16253(14) 0.2486(4) 0.16982(12) 0.0182(6) Uani 1 1 d . . . . .
C30 C 0.05645(14) 0.2890(4) 0.11300(13) 0.0180(6) Uani 1 1 d . . . . .
C31 C -0.02069(15) 0.3004(4) 0.09165(13) 0.0203(6) Uani 1 1 d . . . . .
H31A H -0.0463 0.4065 0.1113 0.024 Uiso 1 1 calc R U . . .
H31B H -0.0467 0.1812 0.1000 0.024 Uiso 1 1 calc R U . . .
C32 C -0.01251(15) 0.3333(4) 0.02379(13) 0.0199(6) Uani 1 1 d . . . . .
C33 C -0.06532(16) 0.3495(4) -0.02034(14) 0.0245(6) Uani 1 1 d . . . . .
H33A H -0.1148 0.3420 -0.0101 0.029 Uiso 1 1 calc R U . . .
C34 C -0.04341(16) 0.3773(4) -0.08028(14) 0.0268(7) Uani 1 1 d . . . . .
H34A H -0.0789 0.3881 -0.1111 0.032 Uiso 1 1 calc R U . . .
C35 C 0.02865(17) 0.3896(4) -0.09641(13) 0.0244(6) Uani 1 1 d . . . . .
H35A H 0.0416 0.4094 -0.1376 0.029 Uiso 1 1 calc R U . . .
C36 C 0.08166(15) 0.3729(4) -0.05231(14) 0.0205(6) Uani 1 1 d . . . . .
C37 C 0.05977(15) 0.3449(4) 0.00817(12) 0.0181(6) Uani 1 1 d . . . . .
C38 C 0.10393(15) 0.3171(4) 0.06221(12) 0.0174(5) Uani 1 1 d . . . . .
C39 C 0.19192(16) 0.3941(4) -0.11580(14) 0.0239(6) Uani 1 1 d . . . . .
C40 C 0.27242(16) 0.4004(4) -0.10884(15) 0.0290(7) Uani 1 1 d . . . . .
H40A H 0.2849 0.3929 -0.0657 0.043 Uiso 1 1 calc R U . . .
H40B H 0.2939 0.2934 -0.1305 0.043 Uiso 1 1 calc R U . . .
H40C H 0.2908 0.5190 -0.1258 0.043 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C19 1.231(3) . ?
N1 C18 1.330(3) . ?
N1 C1 1.374(4) . ?
N2 C19 1.358(4) . ?
N2 C16 1.409(4) . ?
N2 H2A 0.91(4) . ?
C1 C2 1.416(4) . ?
C1 C9 1.405(4) . ?
C2 C3 1.385(4) . ?
C2 H2B 0.9500 . ?
C3 C4 1.422(4) . ?
C3 H3A 0.9500 . ?
C4 C5 1.372(4) . ?
C4 H4B 0.9500 . ?
C5 C9 1.406(4) . ?
C5 C6 1.520(4) . ?
C6 C7 1.563(5) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.517(4) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C10 1.360(4) . ?
C8 C9 1.413(4) . ?
C10 C18 1.438(4) . ?
C10 C11 1.509(4) . ?
C11 C12 1.524(4) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.384(4) . ?
C12 C17 1.407(4) . ?
C13 C14 1.395(4) . ?
C13 H13A 0.9500 . ?
C14 C15 1.396(4) . ?
C14 H14A 0.9500 . ?
C15 C16 1.397(4) . ?
C15 H15A 0.9500 . ?
C16 C17 1.403(4) . ?
C17 C18 1.458(4) . ?
C19 C20 1.507(4) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
O2 C39 1.220(4) . ?
N3 C38 1.328(3) . ?
N3 C21 1.371(4) . ?
N4 C39 1.365(4) . ?
N4 C36 1.402(4) . ?
N4 H4A 0.99(4) . ?
C21 C29 1.404(4) . ?
C21 C22 1.420(4) . ?
C22 C23 1.373(4) . ?
C22 H22A 0.9500 . ?
C23 C24 1.419(4) . ?
C23 H23A 0.9500 . ?
C24 C25 1.376(4) . ?
C24 H24A 0.9500 . ?
C25 C29 1.398(4) . ?
C25 C26 1.524(4) . ?
C26 C27 1.558(4) . ?
C26 H26A 0.9900 . ?
C26 H26B 0.9900 . ?
C27 C28 1.523(4) . ?
C27 H27A 0.9900 . ?
C27 H27B 0.9900 . ?
C28 C30 1.355(4) . ?
C28 C29 1.412(4) . ?
C30 C38 1.440(4) . ?
C30 C31 1.515(4) . ?
C31 C32 1.521(4) . ?
C31 H31A 0.9900 . ?
C31 H31B 0.9900 . ?
C32 C33 1.388(4) . ?
C32 C37 1.393(4) . ?
C33 C34 1.396(4) . ?
C33 H33A 0.9500 . ?
C34 C35 1.392(4) . ?
C34 H34A 0.9500 . ?
C35 C36 1.391(4) . ?
C35 H35A 0.9500 . ?
C36 C37 1.407(4) . ?
C37 C38 1.460(4) . ?
C39 C40 1.509(4) . ?
C40 H40A 0.9800 . ?
C40 H40B 0.9800 . ?
C40 H40C 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
C18 N1 C1 115.0(2) . . ?
C19 N2 C16 129.1(2) . . ?
C19 N2 H2A 117(2) . . ?
C16 N2 H2A 114(2) . . ?
N1 C1 C2 122.9(2) . . ?
N1 C1 C9 120.4(2) . . ?
C2 C1 C9 116.7(2) . . ?
C3 C2 C1 119.4(3) . . ?
C3 C2 H2B 120.3 . . ?
C1 C2 H2B 120.3 . . ?
C2 C3 C4 122.6(3) . . ?
C2 C3 H3A 118.7 . . ?
C4 C3 H3A 118.7 . . ?
C5 C4 C3 118.8(3) . . ?
C5 C4 H4B 120.6 . . ?
C3 C4 H4B 120.6 . . ?
C4 C5 C9 118.5(3) . . ?
C4 C5 C6 132.6(3) . . ?
C9 C5 C6 108.9(3) . . ?
C5 C6 C7 104.7(3) . . ?
C5 C6 H6A 110.8 . . ?
C7 C6 H6A 110.8 . . ?
C5 C6 H6B 110.8 . . ?
C7 C6 H6B 110.8 . . ?
H6A C6 H6B 108.9 . . ?
C8 C7 C6 105.2(2) . . ?
C8 C7 H7A 110.7 . . ?
C6 C7 H7A 110.7 . . ?
C8 C7 H7B 110.7 . . ?
C6 C7 H7B 110.7 . . ?
H7A C7 H7B 108.8 . . ?
C10 C8 C9 116.4(3) . . ?
C10 C8 C7 135.1(3) . . ?
C9 C8 C7 108.5(3) . . ?
C8 C9 C1 123.3(3) . . ?
C8 C9 C5 112.8(3) . . ?
C1 C9 C5 123.9(3) . . ?
C8 C10 C18 117.2(3) . . ?
C8 C10 C11 133.2(3) . . ?
C18 C10 C11 109.6(3) . . ?
C10 C11 C12 103.1(2) . . ?
C10 C11 H11A 111.1 . . ?
C12 C11 H11A 111.1 . . ?
C10 C11 H11B 111.1 . . ?
C12 C11 H11B 111.1 . . ?
H11A C11 H11B 109.1 . . ?
C13 C12 C17 120.2(3) . . ?
C13 C12 C11 130.1(3) . . ?
C17 C12 C11 109.7(2) . . ?
C14 C13 C12 118.8(3) . . ?
C14 C13 H13A 120.6 . . ?
C12 C13 H13A 120.6 . . ?
C13 C14 C15 121.7(3) . . ?
C13 C14 H14A 119.1 . . ?
C15 C14 H14A 119.1 . . ?
C16 C15 C14 119.8(3) . . ?
C16 C15 H15A 120.1 . . ?
C14 C15 H15A 120.1 . . ?
C15 C16 C17 118.7(3) . . ?
C15 C16 N2 125.5(3) . . ?
C17 C16 N2 115.8(2) . . ?
C16 C17 C12 120.8(3) . . ?
C16 C17 C18 129.7(3) . . ?
C12 C17 C18 109.5(2) . . ?
N1 C18 C10 127.6(3) . . ?
N1 C18 C17 124.2(3) . . ?
C10 C18 C17 108.1(2) . . ?
O1 C19 N2 124.0(3) . . ?
O1 C19 C20 122.2(3) . . ?
N2 C19 C20 113.7(2) . . ?
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 . . ?
C38 N3 C21 115.5(2) . . ?
C39 N4 C36 128.3(3) . . ?
C39 N4 H4A 123(2) . . ?
C36 N4 H4A 108(2) . . ?
N3 C21 C29 120.5(2) . . ?
N3 C21 C22 122.8(3) . . ?
C29 C21 C22 116.7(3) . . ?
C23 C22 C21 119.3(3) . . ?
C23 C22 H22A 120.4 . . ?
C21 C22 H22A 120.4 . . ?
C22 C23 C24 123.1(3) . . ?
C22 C23 H23A 118.5 . . ?
C24 C23 H23A 118.5 . . ?
C25 C24 C23 118.4(3) . . ?
C25 C24 H24A 120.8 . . ?
C23 C24 H24A 120.8 . . ?
C24 C25 C29 118.7(3) . . ?
C24 C25 C26 132.9(3) . . ?
C29 C25 C26 108.5(2) . . ?
C25 C26 C27 105.1(2) . . ?
C25 C26 H26A 110.7 . . ?
C27 C26 H26A 110.7 . . ?
C25 C26 H26B 110.7 . . ?
C27 C26 H26B 110.7 . . ?
H26A C26 H26B 108.8 . . ?
C28 C27 C26 104.9(2) . . ?
C28 C27 H27A 110.8 . . ?
C26 C27 H27A 110.8 . . ?
C28 C27 H27B 110.8 . . ?
C26 C27 H27B 110.8 . . ?
H27A C27 H27B 108.8 . . ?
C30 C28 C29 116.8(2) . . ?
C30 C28 C27 134.9(2) . . ?
C29 C28 C27 108.3(2) . . ?
C25 C29 C28 113.2(2) . . ?
C25 C29 C21 123.9(2) . . ?
C28 C29 C21 122.8(2) . . ?
C28 C30 C38 117.4(2) . . ?
C28 C30 C31 133.1(3) . . ?
C38 C30 C31 109.5(2) . . ?
C30 C31 C32 102.6(2) . . ?
C30 C31 H31A 111.2 . . ?
C32 C31 H31A 111.2 . . ?
C30 C31 H31B 111.2 . . ?
C32 C31 H31B 111.2 . . ?
H31A C31 H31B 109.2 . . ?
C33 C32 C37 120.5(3) . . ?
C33 C32 C31 129.1(3) . . ?
C37 C32 C31 110.4(2) . . ?
C32 C33 C34 117.8(3) . . ?
C32 C33 H33A 121.1 . . ?
C34 C33 H33A 121.1 . . ?
C33 C34 C35 122.2(3) . . ?
C33 C34 H34A 118.9 . . ?
C35 C34 H34A 118.9 . . ?
C36 C35 C34 120.1(3) . . ?
C36 C35 H35A 119.9 . . ?
C34 C35 H35A 119.9 . . ?
C37 C36 C35 117.9(3) . . ?
C37 C36 N4 115.8(3) . . ?
C35 C36 N4 126.3(3) . . ?
C36 C37 C32 121.5(3) . . ?
C36 C37 C38 128.8(3) . . ?
C32 C37 C38 109.6(2) . . ?
N3 C38 C30 126.9(2) . . ?
N3 C38 C37 125.2(2) . . ?
C30 C38 C37 107.8(2) . . ?
O2 C39 N4 123.8(3) . . ?
O2 C39 C40 122.5(3) . . ?
N4 C39 C40 113.7(3) . . ?
C39 C40 H40A 109.5 . . ?
C39 C40 H40B 109.5 . . ?
H40A C40 H40B 109.5 . . ?
C39 C40 H40C 109.5 . . ?
H40A C40 H40C 109.5 . . ?
H40B C40 H40C 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
C18 N1 C1 C2 179.2(3) . . . . ?
C18 N1 C1 C9 -1.1(4) . . . . ?
N1 C1 C2 C3 179.4(3) . . . . ?
C9 C1 C2 C3 -0.2(4) . . . . ?
C1 C2 C3 C4 0.0(4) . . . . ?
C2 C3 C4 C5 -0.2(4) . . . . ?
C3 C4 C5 C9 0.6(4) . . . . ?
C3 C4 C5 C6 -179.8(3) . . . . ?
C4 C5 C6 C7 -179.3(3) . . . . ?
C9 C5 C6 C7 0.3(3) . . . . ?
C5 C6 C7 C8 0.4(3) . . . . ?
C6 C7 C8 C10 179.7(3) . . . . ?
C6 C7 C8 C9 -1.0(3) . . . . ?
C10 C8 C9 C1 0.3(4) . . . . ?
C7 C8 C9 C1 -179.1(2) . . . . ?
C10 C8 C9 C5 -179.3(2) . . . . ?
C7 C8 C9 C5 1.3(3) . . . . ?
N1 C1 C9 C8 1.4(4) . . . . ?
C2 C1 C9 C8 -178.9(2) . . . . ?
N1 C1 C9 C5 -179.0(2) . . . . ?
C2 C1 C9 C5 0.7(4) . . . . ?
C4 C5 C9 C8 178.7(2) . . . . ?
C6 C5 C9 C8 -1.0(3) . . . . ?
C4 C5 C9 C1 -0.9(4) . . . . ?
C6 C5 C9 C1 179.4(3) . . . . ?
C9 C8 C10 C18 -2.1(4) . . . . ?
C7 C8 C10 C18 177.2(3) . . . . ?
C9 C8 C10 C11 179.2(3) . . . . ?
C7 C8 C10 C11 -1.5(5) . . . . ?
C8 C10 C11 C12 177.5(3) . . . . ?
C18 C10 C11 C12 -1.3(3) . . . . ?
C10 C11 C12 C13 -179.2(3) . . . . ?
C10 C11 C12 C17 0.6(3) . . . . ?
C17 C12 C13 C14 -1.3(4) . . . . ?
C11 C12 C13 C14 178.5(3) . . . . ?
C12 C13 C14 C15 0.7(4) . . . . ?
C13 C14 C15 C16 0.1(4) . . . . ?
C14 C15 C16 C17 -0.2(4) . . . . ?
C14 C15 C16 N2 179.8(3) . . . . ?
C19 N2 C16 C15 5.6(5) . . . . ?
C19 N2 C16 C17 -174.4(3) . . . . ?
C15 C16 C17 C12 -0.5(4) . . . . ?
N2 C16 C17 C12 179.6(2) . . . . ?
C15 C16 C17 C18 -179.1(3) . . . . ?
N2 C16 C17 C18 1.0(4) . . . . ?
C13 C12 C17 C16 1.3(4) . . . . ?
C11 C12 C17 C16 -178.6(2) . . . . ?
C13 C12 C17 C18 -179.9(2) . . . . ?
C11 C12 C17 C18 0.3(3) . . . . ?
C1 N1 C18 C10 -0.8(4) . . . . ?
C1 N1 C18 C17 179.2(2) . . . . ?
C8 C10 C18 N1 2.6(4) . . . . ?
C11 C10 C18 N1 -178.4(3) . . . . ?
C8 C10 C18 C17 -177.5(2) . . . . ?
C11 C10 C18 C17 1.5(3) . . . . ?
C16 C17 C18 N1 -2.4(4) . . . . ?
C12 C17 C18 N1 178.8(2) . . . . ?
C16 C17 C18 C10 177.6(3) . . . . ?
C12 C17 C18 C10 -1.1(3) . . . . ?
C16 N2 C19 O1 -2.3(5) . . . . ?
C16 N2 C19 C20 176.9(3) . . . . ?
C38 N3 C21 C29 -1.7(4) . . . . ?
C38 N3 C21 C22 178.4(2) . . . . ?
N3 C21 C22 C23 -178.7(3) . . . . ?
C29 C21 C22 C23 1.4(4) . . . . ?
C21 C22 C23 C24 -0.8(4) . . . . ?
C22 C23 C24 C25 -0.4(4) . . . . ?
C23 C24 C25 C29 1.1(4) . . . . ?
C23 C24 C25 C26 -179.6(3) . . . . ?
C24 C25 C26 C27 -179.3(3) . . . . ?
C29 C25 C26 C27 0.1(3) . . . . ?
C25 C26 C27 C28 0.8(3) . . . . ?
C26 C27 C28 C30 178.0(3) . . . . ?
C26 C27 C28 C29 -1.4(3) . . . . ?
C24 C25 C29 C28 178.4(2) . . . . ?
C26 C25 C29 C28 -1.0(3) . . . . ?
C24 C25 C29 C21 -0.5(4) . . . . ?
C26 C25 C29 C21 -180.0(2) . . . . ?
C30 C28 C29 C25 -178.0(2) . . . . ?
C27 C28 C29 C25 1.5(3) . . . . ?
C30 C28 C29 C21 1.0(4) . . . . ?
C27 C28 C29 C21 -179.5(2) . . . . ?
N3 C21 C29 C25 179.3(2) . . . . ?
C22 C21 C29 C25 -0.7(4) . . . . ?
N3 C21 C29 C28 0.5(4) . . . . ?
C22 C21 C29 C28 -179.6(2) . . . . ?
C29 C28 C30 C38 -1.1(4) . . . . ?
C27 C28 C30 C38 179.6(3) . . . . ?
C29 C28 C30 C31 177.5(3) . . . . ?
C27 C28 C30 C31 -1.8(6) . . . . ?
C28 C30 C31 C32 -177.5(3) . . . . ?
C38 C30 C31 C32 1.2(3) . . . . ?
C30 C31 C32 C33 177.8(3) . . . . ?
C30 C31 C32 C37 -1.5(3) . . . . ?
C37 C32 C33 C34 0.1(4) . . . . ?
C31 C32 C33 C34 -179.1(3) . . . . ?
C32 C33 C34 C35 -0.3(4) . . . . ?
C33 C34 C35 C36 0.4(4) . . . . ?
C34 C35 C36 C37 -0.4(4) . . . . ?
C34 C35 C36 N4 179.5(3) . . . . ?
C39 N4 C36 C37 175.3(3) . . . . ?
C39 N4 C36 C35 -4.6(5) . . . . ?
C35 C36 C37 C32 0.2(4) . . . . ?
N4 C36 C37 C32 -179.7(2) . . . . ?
C35 C36 C37 C38 177.8(3) . . . . ?
N4 C36 C37 C38 -2.1(4) . . . . ?
C33 C32 C37 C36 -0.1(4) . . . . ?
C31 C32 C37 C36 179.3(2) . . . . ?
C33 C32 C37 C38 -178.1(2) . . . . ?
C31 C32 C37 C38 1.3(3) . . . . ?
C21 N3 C38 C30 1.6(4) . . . . ?
C21 N3 C38 C37 -176.8(2) . . . . ?
C28 C30 C38 N3 -0.2(4) . . . . ?
C31 C30 C38 N3 -179.1(2) . . . . ?
C28 C30 C38 C37 178.4(2) . . . . ?
C31 C30 C38 C37 -0.5(3) . . . . ?
C36 C37 C38 N3 0.4(4) . . . . ?
C32 C37 C38 N3 178.2(2) . . . . ?
C36 C37 C38 C30 -178.3(3) . . . . ?
C32 C37 C38 C30 -0.5(3) . . . . ?
C36 N4 C39 O2 0.1(5) . . . . ?
C36 N4 C39 C40 179.8(2) . . . . ?

_refine_diff_density_max         0.232
_refine_diff_density_min         -0.297
_refine_diff_density_rms         0.055

