# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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_P21_a
_database_code_depnum_ccdc_archive 'CCDC 1970159'
loop_
_audit_author_name
_audit_author_address
'Dongsik Nam'
;Ulsan National Institute of Science and Technology
South Korea
;
_audit_update_record             
;
2019-12-05 deposited with the CCDC.	2020-04-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        5ad
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H11 N5 O2'
_chemical_formula_weight         305.30

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

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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'

_cell_length_a                   7.1117(14)
_cell_length_b                   14.251(3)
_cell_length_c                   7.5497(15)
_cell_angle_alpha                90
_cell_angle_beta                 102.83(3)
_cell_angle_gamma                90
_cell_volume                     746.0(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    3389
_cell_measurement_theta_min      3.115
_cell_measurement_theta_max      27.468

_exptl_crystal_description       Block
_exptl_crystal_colour            Colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.359
_exptl_crystal_F_000             316
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.720
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.130
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.935
_exptl_absorpt_correction_T_max  0.988
_exptl_absorpt_process_details   'Rigaku Rapid Auto'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'imaging plate'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7109
_diffrn_reflns_av_unetI/netI     0.0269
_diffrn_reflns_av_R_equivalents  0.0182
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         3.115
_diffrn_reflns_theta_max         27.468
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             3389
_reflns_number_gt                2490
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.918
_reflns_Friedel_fraction_max     0.992
_reflns_Friedel_fraction_full    0.995

_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       'Rigaku Rapid Auto'
_computing_cell_refinement       'Rigaku Rapid Auto'
_computing_data_reduction        'Rigaku Rapid Auto'
_computing_structure_solution    SHELXS
_computing_structure_refinement  SHELXL
_computing_molecular_graphics    ORTEP
_computing_publication_material  CIFTAB
_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)+(0.0306P)²+0.0435P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 888 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3389
_refine_ls_number_parameters     208
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0631
_refine_ls_R_factor_gt           0.0401
_refine_ls_wR_factor_ref         0.0777
_refine_ls_wR_factor_gt          0.0721
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_restrained_S_all      1.030
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.5814(4) 0.51877(17) 0.1513(3) 0.0511(6) Uani 1 1 d . . . . .
C2 C 0.5952(3) 0.45063(16) 0.3004(3) 0.0465(5) Uani 1 1 d . . . . .
C3 C 0.6364(4) 0.47896(17) 0.4817(3) 0.0530(6) Uani 1 1 d . . . . .
H3 H 0.6505 0.5424 0.5107 0.064 Uiso 1 1 calc R U . . .
C4 C 0.6563(4) 0.41294(17) 0.6181(3) 0.0542(6) Uani 1 1 d . . . . .
H4 H 0.6868 0.4309 0.7395 0.065 Uiso 1 1 calc R U . . .
C5 C 0.6302(3) 0.32004(18) 0.5707(3) 0.0481(6) Uani 1 1 d . . . . .
C6 C 0.5836(4) 0.29005(17) 0.3940(3) 0.0528(6) Uani 1 1 d . . . . .
H6 H 0.5638 0.2267 0.3663 0.063 Uiso 1 1 calc R U . . .
C7 C 0.5670(3) 0.35607(16) 0.2587(3) 0.0526(6) Uani 1 1 d . . . . .
H7 H 0.5364 0.3372 0.1378 0.063 Uiso 1 1 calc R U . . .
C8 C 0.4359(4) 0.53464(17) 0.0007(3) 0.0602(7) Uani 1 1 d . . . . .
C9 C 0.2487(6) 0.49394(19) -0.0392(4) 0.0713(8) Uani 1 1 d . . . . .
C10 C 0.9109(4) 0.5977(2) 0.2477(4) 0.0736(8) Uani 1 1 d . . . . .
H10A H 0.9985 0.6153 0.1715 0.088 Uiso 1 1 calc R U . . .
H10B H 0.9585 0.5399 0.3097 0.088 Uiso 1 1 calc R U . . .
C11 C 0.9132(4) 0.6734(2) 0.3874(4) 0.0624(7) Uani 1 1 d . . . . .
C12 C 0.8576(4) 0.7644(2) 0.3371(4) 0.0706(8) Uani 1 1 d . . . . .
H12 H 0.8160 0.7792 0.2147 0.085 Uiso 1 1 calc R U . . .
C13 C 0.8632(5) 0.8328(2) 0.4652(5) 0.0861(10) Uani 1 1 d . . . . .
H13 H 0.8249 0.8936 0.4296 0.103 Uiso 1 1 calc R U . . .
C14 C 0.9251(5) 0.8118(3) 0.6461(6) 0.0966(12) Uani 1 1 d . . . . .
H14 H 0.9275 0.8582 0.7332 0.116 Uiso 1 1 calc R U . . .
C15 C 0.9836(6) 0.7219(3) 0.6984(5) 0.1030(12) Uani 1 1 d . . . . .
H15 H 1.0269 0.7075 0.8208 0.124 Uiso 1 1 calc R U . . .
C16 C 0.9779(5) 0.6542(2) 0.5702(4) 0.0856(10) Uani 1 1 d . . . . .
H16 H 1.0184 0.5938 0.6064 0.103 Uiso 1 1 calc R U . . .
N1 N 0.4902(4) 0.60245(16) -0.1036(3) 0.0777(7) Uani 1 1 d . . . . .
N2 N 0.6636(4) 0.63040(17) -0.0244(3) 0.0792(7) Uani 1 1 d . . . . .
N3 N 0.7194(3) 0.58030(15) 0.1317(3) 0.0629(6) Uani 1 1 d . . . . .
N4 N 0.6541(3) 0.24855(18) 0.7157(3) 0.0674(7) Uani 1 1 d . . . . .
N5 N 0.0970(5) 0.4632(2) -0.0664(4) 0.1002(10) Uani 1 1 d . . . . .
O1 O 0.6350(3) 0.16616(15) 0.6732(3) 0.0883(7) Uani 1 1 d . . . . .
O2 O 0.6964(4) 0.27567(19) 0.8721(3) 0.1130(9) 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 N3 1.348(3) . ?
C1 C8 1.375(3) . ?
C1 C2 1.473(3) . ?
C2 C7 1.388(3) . ?
C2 C3 1.395(3) . ?
C3 C4 1.378(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.373(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.370(3) . ?
C5 N4 1.478(3) . ?
C6 C7 1.374(3) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C8 N1 1.356(3) . ?
C8 C9 1.422(5) . ?
C9 N5 1.140(4) . ?
C10 N3 1.468(3) . ?
C10 C11 1.506(4) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C16 1.381(4) . ?
C11 C12 1.384(4) . ?
C12 C13 1.367(4) . ?
C12 H12 0.9300 . ?
C13 C14 1.372(5) . ?
C13 H13 0.9300 . ?
C14 C15 1.377(6) . ?
C14 H14 0.9300 . ?
C15 C16 1.361(5) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
N1 N2 1.307(3) . ?
N2 N3 1.360(3) . ?
N4 O2 1.215(3) . ?
N4 O1 1.217(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
N3 C1 C8 103.6(2) . . ?
N3 C1 C2 125.9(2) . . ?
C8 C1 C2 130.6(2) . . ?
C7 C2 C3 119.5(2) . . ?
C7 C2 C1 119.0(2) . . ?
C3 C2 C1 121.5(2) . . ?
C4 C3 C2 120.0(2) . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
C5 C4 C3 118.6(2) . . ?
C5 C4 H4 120.7 . . ?
C3 C4 H4 120.7 . . ?
C6 C5 C4 123.0(2) . . ?
C6 C5 N4 118.0(2) . . ?
C4 C5 N4 119.0(2) . . ?
C5 C6 C7 118.2(2) . . ?
C5 C6 H6 120.9 . . ?
C7 C6 H6 120.9 . . ?
C6 C7 C2 120.8(2) . . ?
C6 C7 H7 119.6 . . ?
C2 C7 H7 119.6 . . ?
N1 C8 C1 109.8(3) . . ?
N1 C8 C9 122.8(2) . . ?
C1 C8 C9 127.2(2) . . ?
N5 C9 C8 177.6(3) . . ?
N3 C10 C11 113.8(2) . . ?
N3 C10 H10A 108.8 . . ?
C11 C10 H10A 108.8 . . ?
N3 C10 H10B 108.8 . . ?
C11 C10 H10B 108.8 . . ?
H10A C10 H10B 107.7 . . ?
C16 C11 C12 118.1(3) . . ?
C16 C11 C10 120.5(3) . . ?
C12 C11 C10 121.4(3) . . ?
C13 C12 C11 120.8(3) . . ?
C13 C12 H12 119.6 . . ?
C11 C12 H12 119.6 . . ?
C12 C13 C14 120.1(4) . . ?
C12 C13 H13 120.0 . . ?
C14 C13 H13 120.0 . . ?
C13 C14 C15 119.9(4) . . ?
C13 C14 H14 120.1 . . ?
C15 C14 H14 120.1 . . ?
C16 C15 C14 119.7(3) . . ?
C16 C15 H15 120.1 . . ?
C14 C15 H15 120.1 . . ?
C15 C16 C11 121.4(3) . . ?
C15 C16 H16 119.3 . . ?
C11 C16 H16 119.3 . . ?
N2 N1 C8 108.2(2) . . ?
N1 N2 N3 107.5(2) . . ?
C1 N3 N2 110.9(2) . . ?
C1 N3 C10 130.2(2) . . ?
N2 N3 C10 118.8(2) . . ?
O2 N4 O1 123.5(3) . . ?
O2 N4 C5 117.6(3) . . ?
O1 N4 C5 118.8(2) . . ?

_refine_diff_density_max         0.103
_refine_diff_density_min         -0.156
_refine_diff_density_rms         0.022

####################################################################### 
# 
# 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_P21c_a
_database_code_depnum_ccdc_archive 'CCDC 1970161'
loop_
_audit_author_name
_audit_author_address
'Dongsik Nam'
;Ulsan National Institute of Science and Technology
South Korea
;
_audit_update_record             
;
2019-12-05 deposited with the CCDC.	2020-04-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        7ab
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H18 N4 O2'
_chemical_formula_weight         334.37

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

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

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

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

_cell_length_a                   9.6779(19)
_cell_length_b                   15.962(3)
_cell_length_c                   12.006(2)
_cell_angle_alpha                90
_cell_angle_beta                 108.70(3)
_cell_angle_gamma                90
_cell_volume                     1756.8(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    4008
_cell_measurement_theta_min      3.118
_cell_measurement_theta_max      27.459

_exptl_crystal_description       Block
_exptl_crystal_colour            Colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.264
_exptl_crystal_F_000             704
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.280
_exptl_crystal_size_min          0.140
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.977
_exptl_absorpt_correction_T_max  0.988
_exptl_absorpt_process_details   'Rigaku Rapid Auto'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'imaging plate'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            16732
_diffrn_reflns_av_unetI/netI     0.0284
_diffrn_reflns_av_R_equivalents  0.0350
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.118
_diffrn_reflns_theta_max         27.459
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             4008
_reflns_number_gt                2666
_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       'Rigaku Rapid Auto'
_computing_cell_refinement       'Rigaku Rapid Auto'
_computing_data_reduction        'Rigaku Rapid Auto'
_computing_structure_solution    SHELXS
_computing_structure_refinement  SHELXL
_computing_molecular_graphics    ORTEP
_computing_publication_material  CIFTAB
_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)+(0.0631P)²+0.5194P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4008
_refine_ls_number_parameters     227
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0959
_refine_ls_R_factor_gt           0.0584
_refine_ls_wR_factor_ref         0.1495
_refine_ls_wR_factor_gt          0.1333
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_restrained_S_all      1.027
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.3147(2) 0.61376(11) 0.45023(16) 0.0429(4) Uani 1 1 d . . . . .
C2 C 0.4977(3) 0.68447(14) 0.62452(18) 0.0684(7) Uani 1 1 d . . . . .
H2A H 0.5789 0.6463 0.6350 0.082 Uiso 1 1 calc R U . . .
H2B H 0.4484 0.6712 0.6810 0.082 Uiso 1 1 calc R U . . .
C3 C 0.5459(4) 0.77430(17) 0.6335(2) 0.0994(10) Uani 1 1 d . . . . .
H3A H 0.4942 0.8071 0.6754 0.119 Uiso 1 1 calc R U . . .
H3B H 0.6498 0.7787 0.6745 0.119 Uiso 1 1 calc R U . . .
C4 C 0.4163(3) 0.75032(13) 0.44146(19) 0.0588(6) Uani 1 1 d . . . . .
C5 C 0.3285(2) 0.55631(11) 0.36972(16) 0.0436(4) Uani 1 1 d . . . . .
C6 C 0.4431(2) 0.54398(11) 0.31575(15) 0.0412(4) Uani 1 1 d . . . . .
C7 C 0.5866(2) 0.56864(12) 0.37021(17) 0.0491(5) Uani 1 1 d . . . . .
H7 H 0.6116 0.5967 0.4418 0.059 Uiso 1 1 calc R U . . .
C8 C 0.6924(2) 0.55195(14) 0.31903(18) 0.0548(5) Uani 1 1 d . . . . .
H8 H 0.7877 0.5692 0.3569 0.066 Uiso 1 1 calc R U . . .
C9 C 0.6606(2) 0.51022(13) 0.21303(18) 0.0547(5) Uani 1 1 d . . . . .
C10 C 0.7769(3) 0.4912(2) 0.1579(2) 0.0856(8) Uani 1 1 d . . . . .
H10A H 0.7850 0.5374 0.1091 0.128 Uiso 1 1 calc R U . . .
H10B H 0.7510 0.4414 0.1110 0.128 Uiso 1 1 calc R U . . .
H10C H 0.8686 0.4829 0.2186 0.128 Uiso 1 1 calc R U . . .
C11 C 0.5180(2) 0.48551(13) 0.15924(18) 0.0565(5) Uani 1 1 d . . . . .
H11 H 0.4939 0.4569 0.0881 0.068 Uiso 1 1 calc R U . . .
C12 C 0.4107(2) 0.50226(12) 0.20836(17) 0.0512(5) Uani 1 1 d . . . . .
H12 H 0.3153 0.4856 0.1695 0.061 Uiso 1 1 calc R U . . .
C13 C 0.1196(3) 0.63388(13) 0.5486(2) 0.0592(6) Uani 1 1 d . . . . .
H13A H 0.1898 0.6377 0.6269 0.071 Uiso 1 1 calc R U . . .
H13B H 0.0390 0.5994 0.5532 0.071 Uiso 1 1 calc R U . . .
C14 C 0.0637(2) 0.72016(13) 0.50771(19) 0.0543(5) Uani 1 1 d . . . . .
C15 C 0.0870(3) 0.78427(17) 0.5894(2) 0.0804(8) Uani 1 1 d . . . . .
H15 H 0.1369 0.7730 0.6681 0.096 Uiso 1 1 calc R U . . .
C16 C 0.0380(4) 0.86404(19) 0.5565(3) 0.1015(10) Uani 1 1 d . . . . .
H16 H 0.0550 0.9063 0.6126 0.122 Uiso 1 1 calc R U . . .
C17 C -0.0352(3) 0.88116(19) 0.4420(4) 0.0949(10) Uani 1 1 d . . . . .
H17 H -0.0699 0.9350 0.4202 0.114 Uiso 1 1 calc R U . . .
C18 C -0.0584(3) 0.8200(2) 0.3586(3) 0.0903(9) Uani 1 1 d . . . . .
H18 H -0.1079 0.8322 0.2802 0.108 Uiso 1 1 calc R U . . .
C19 C -0.0071(3) 0.73837(16) 0.3918(2) 0.0742(7) Uani 1 1 d . . . . .
H19 H -0.0211 0.6967 0.3351 0.089 Uiso 1 1 calc R U . . .
N1 N 0.21040(18) 0.50439(10) 0.34430(15) 0.0528(4) Uani 1 1 d . . . . .
N2 N 0.12668(19) 0.52699(11) 0.40634(16) 0.0574(5) Uani 1 1 d . . . . .
N3 N 0.18872(18) 0.59341(10) 0.47045(14) 0.0501(4) Uani 1 1 d . . . . .
N4 N 0.39771(18) 0.68285(9) 0.50421(13) 0.0480(4) Uani 1 1 d . . . . .
O1 O 0.5117(2) 0.80299(10) 0.51405(16) 0.0901(6) Uani 1 1 d . . . . .
O2 O 0.3602(2) 0.76299(11) 0.33902(14) 0.0831(6) 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 N3 1.356(2) . ?
C1 C5 1.370(3) . ?
C1 N4 1.396(2) . ?
C2 N4 1.459(3) . ?
C2 C3 1.501(3) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 O1 1.439(3) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 O2 1.192(3) . ?
C4 O1 1.342(3) . ?
C4 N4 1.359(2) . ?
C5 N1 1.365(2) . ?
C5 C6 1.467(3) . ?
C6 C7 1.389(3) . ?
C6 C12 1.395(3) . ?
C7 C8 1.378(3) . ?
C7 H7 0.9300 . ?
C8 C9 1.381(3) . ?
C8 H8 0.9300 . ?
C9 C11 1.381(3) . ?
C9 C10 1.508(3) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 C12 1.375(3) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C13 N3 1.465(3) . ?
C13 C14 1.503(3) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 C19 1.371(3) . ?
C14 C15 1.385(3) . ?
C15 C16 1.372(4) . ?
C15 H15 0.9300 . ?
C16 C17 1.357(4) . ?
C16 H16 0.9300 . ?
C17 C18 1.365(4) . ?
C17 H17 0.9300 . ?
C18 C19 1.405(4) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?
N1 N2 1.315(2) . ?
N2 N3 1.334(2) . ?

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
N3 C1 C5 105.22(16) . . ?
N3 C1 N4 121.53(17) . . ?
C5 C1 N4 133.22(18) . . ?
N4 C2 C3 100.39(18) . . ?
N4 C2 H2A 111.7 . . ?
C3 C2 H2A 111.7 . . ?
N4 C2 H2B 111.7 . . ?
C3 C2 H2B 111.7 . . ?
H2A C2 H2B 109.5 . . ?
O1 C3 C2 105.39(19) . . ?
O1 C3 H3A 110.7 . . ?
C2 C3 H3A 110.7 . . ?
O1 C3 H3B 110.7 . . ?
C2 C3 H3B 110.7 . . ?
H3A C3 H3B 108.8 . . ?
O2 C4 O1 123.7(2) . . ?
O2 C4 N4 127.5(2) . . ?
O1 C4 N4 108.79(18) . . ?
N1 C5 C1 107.48(17) . . ?
N1 C5 C6 121.17(16) . . ?
C1 C5 C6 131.33(17) . . ?
C7 C6 C12 117.74(18) . . ?
C7 C6 C5 122.55(17) . . ?
C12 C6 C5 119.64(17) . . ?
C8 C7 C6 120.58(19) . . ?
C8 C7 H7 119.7 . . ?
C6 C7 H7 119.7 . . ?
C7 C8 C9 121.74(19) . . ?
C7 C8 H8 119.1 . . ?
C9 C8 H8 119.1 . . ?
C11 C9 C8 117.58(19) . . ?
C11 C9 C10 120.8(2) . . ?
C8 C9 C10 121.6(2) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C12 C11 C9 121.5(2) . . ?
C12 C11 H11 119.2 . . ?
C9 C11 H11 119.2 . . ?
C11 C12 C6 120.82(19) . . ?
C11 C12 H12 119.6 . . ?
C6 C12 H12 119.6 . . ?
N3 C13 C14 112.66(17) . . ?
N3 C13 H13A 109.1 . . ?
C14 C13 H13A 109.1 . . ?
N3 C13 H13B 109.1 . . ?
C14 C13 H13B 109.1 . . ?
H13A C13 H13B 107.8 . . ?
C19 C14 C15 118.5(2) . . ?
C19 C14 C13 122.4(2) . . ?
C15 C14 C13 119.1(2) . . ?
C16 C15 C14 121.2(3) . . ?
C16 C15 H15 119.4 . . ?
C14 C15 H15 119.4 . . ?
C17 C16 C15 119.9(3) . . ?
C17 C16 H16 120.0 . . ?
C15 C16 H16 120.0 . . ?
C16 C17 C18 120.6(3) . . ?
C16 C17 H17 119.7 . . ?
C18 C17 H17 119.7 . . ?
C17 C18 C19 119.7(3) . . ?
C17 C18 H18 120.2 . . ?
C19 C18 H18 120.2 . . ?
C14 C19 C18 120.0(3) . . ?
C14 C19 H19 120.0 . . ?
C18 C19 H19 120.0 . . ?
N2 N1 C5 109.30(16) . . ?
N1 N2 N3 107.44(15) . . ?
N2 N3 C1 110.55(16) . . ?
N2 N3 C13 120.40(17) . . ?
C1 N3 C13 129.04(17) . . ?
C4 N4 C1 121.85(16) . . ?
C4 N4 C2 111.78(17) . . ?
C1 N4 C2 125.05(16) . . ?
C4 O1 C3 109.79(18) . . ?

_refine_diff_density_max         0.175
_refine_diff_density_min         -0.207
_refine_diff_density_rms         0.034

####################################################################### 
# 
# 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_Pbca_a
_database_code_depnum_ccdc_archive 'CCDC 1970162'
loop_
_audit_author_name
_audit_author_address
'Dongsik Nam'
;Ulsan National Institute of Science and Technology
South Korea
;
_audit_update_record             
;
2019-12-05 deposited with the CCDC.	2020-04-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        7ae
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H18 N4 O3'
_chemical_formula_weight         350.37

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

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

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

_cell_length_a                   14.942(3)
_cell_length_b                   12.891(3)
_cell_length_c                   17.930(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3453.6(12)
_cell_formula_units_Z            8
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    3956
_cell_measurement_theta_min      3.085
_cell_measurement_theta_max      27.466

_exptl_crystal_description       Block
_exptl_crystal_colour            Orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.348
_exptl_crystal_F_000             1472
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.230
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.220
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.979
_exptl_absorpt_correction_T_max  0.980
_exptl_absorpt_process_details   'Rigaku Rapid Auto'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'imaging plate'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            30009
_diffrn_reflns_av_unetI/netI     0.0267
_diffrn_reflns_av_R_equivalents  0.0453
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         3.085
_diffrn_reflns_theta_max         27.466
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3956
_reflns_number_gt                2672
_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       'Rigaku Rapid Auto'
_computing_cell_refinement       'Rigaku Rapid Auto'
_computing_data_reduction        'Rigaku Rapid Auto'
_computing_structure_solution    SHELXS
_computing_structure_refinement  SHELXL
_computing_molecular_graphics    ORTEP
_computing_publication_material  CIFTAB
_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)+(0.0432P)²+0.7003P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3956
_refine_ls_number_parameters     236
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0887
_refine_ls_R_factor_gt           0.0512
_refine_ls_wR_factor_ref         0.1121
_refine_ls_wR_factor_gt          0.0993
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.038
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.30829(10) 0.71713(11) 0.50468(9) 0.0451(4) Uani 1 1 d . . . . .
C2 C 0.22027(12) 0.73279(15) 0.61565(11) 0.0599(5) Uani 1 1 d . . . . .
C3 C 0.15453(13) 0.89069(16) 0.60085(12) 0.0728(6) Uani 1 1 d . . . . .
H3A H 0.1644 0.9570 0.6251 0.087 Uiso 1 1 calc R U . . .
H3B H 0.0931 0.8878 0.5835 0.087 Uiso 1 1 calc R U . . .
C4 C 0.21870(13) 0.87616(14) 0.53691(11) 0.0630(5) Uani 1 1 d . . . . .
H4A H 0.1904 0.8903 0.4893 0.076 Uiso 1 1 calc R U . . .
H4B H 0.2714 0.9195 0.5423 0.076 Uiso 1 1 calc R U . . .
C5 C 0.39424(10) 0.68590(11) 0.52046(9) 0.0446(4) Uani 1 1 d . . . . .
C6 C 0.44945(10) 0.68528(12) 0.58844(9) 0.0429(4) Uani 1 1 d . . . . .
C7 C 0.50760(10) 0.60218(12) 0.59936(9) 0.0476(4) Uani 1 1 d . . . . .
H7 H 0.5095 0.5494 0.5640 0.057 Uiso 1 1 calc R U . . .
C8 C 0.56227(12) 0.59590(14) 0.66088(10) 0.0546(4) Uani 1 1 d . . . . .
H8 H 0.6009 0.5399 0.6667 0.066 Uiso 1 1 calc R U . . .
C9 C 0.55929(12) 0.67303(14) 0.71366(10) 0.0569(5) Uani 1 1 d . . . . .
H9 H 0.5955 0.6686 0.7557 0.068 Uiso 1 1 calc R U . . .
C10 C 0.50312(12) 0.75681(14) 0.70484(9) 0.0546(4) Uani 1 1 d . . . . .
H10 H 0.5019 0.8089 0.7407 0.066 Uiso 1 1 calc R U . . .
C11 C 0.44836(10) 0.76348(12) 0.64248(9) 0.0462(4) Uani 1 1 d . . . . .
C12 C 0.39275(15) 0.92895(15) 0.68051(12) 0.0752(6) Uani 1 1 d . . . . .
H12A H 0.3743 0.9043 0.7286 0.113 Uiso 1 1 calc R U . . .
H12B H 0.3523 0.9820 0.6639 0.113 Uiso 1 1 calc R U . . .
H12C H 0.4521 0.9570 0.6839 0.113 Uiso 1 1 calc R U . . .
C13 C 0.21259(12) 0.69444(14) 0.38734(11) 0.0628(5) Uani 1 1 d . . . . .
H13A H 0.2271 0.7216 0.3384 0.075 Uiso 1 1 calc R U . . .
H13B H 0.1703 0.7415 0.4106 0.075 Uiso 1 1 calc R U . . .
C14 C 0.17034(12) 0.58922(13) 0.37931(10) 0.0529(4) Uani 1 1 d . . . . .
C15 C 0.12235(15) 0.54649(17) 0.43660(11) 0.0722(6) Uani 1 1 d . . . . .
H15 H 0.1154 0.5834 0.4808 0.087 Uiso 1 1 calc R U . . .
C16 C 0.08429(16) 0.4498(2) 0.42983(15) 0.0869(7) Uani 1 1 d . . . . .
H16 H 0.0524 0.4217 0.4695 0.104 Uiso 1 1 calc R U . . .
C17 C 0.09290(17) 0.39539(18) 0.36567(17) 0.0867(7) Uani 1 1 d . . . . .
H17 H 0.0662 0.3305 0.3611 0.104 Uiso 1 1 calc R U . . .
C18 C 0.14051(17) 0.4355(2) 0.30818(16) 0.0883(7) Uani 1 1 d . . . . .
H18 H 0.1471 0.3978 0.2643 0.106 Uiso 1 1 calc R U . . .
C19 C 0.17950(14) 0.53299(17) 0.31470(12) 0.0721(6) Uani 1 1 d . . . . .
H19 H 0.2120 0.5603 0.2751 0.086 Uiso 1 1 calc R U . . .
N1 N 0.24046(9) 0.76581(10) 0.54523(8) 0.0501(3) Uani 1 1 d . . . . .
N2 N 0.29443(9) 0.68900(11) 0.43283(8) 0.0529(4) Uani 1 1 d . . . . .
N3 N 0.36718(10) 0.64396(12) 0.40407(8) 0.0612(4) Uani 1 1 d . . . . .
N4 N 0.42768(9) 0.64140(11) 0.45734(8) 0.0547(4) Uani 1 1 d . . . . .
O1 O 0.17307(9) 0.80637(11) 0.65127(8) 0.0775(4) Uani 1 1 d . . . . .
O2 O 0.23947(10) 0.65082(11) 0.64334(8) 0.0804(4) Uani 1 1 d . . . . .
O3 O 0.39210(8) 0.84509(9) 0.62866(7) 0.0592(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 1.354(2) . ?
C1 C5 1.375(2) . ?
C1 N1 1.396(2) . ?
C2 O2 1.202(2) . ?
C2 O1 1.343(2) . ?
C2 N1 1.366(2) . ?
C3 O1 1.441(2) . ?
C3 C4 1.506(3) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 N1 1.467(2) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 N4 1.364(2) . ?
C5 C6 1.472(2) . ?
C6 C7 1.393(2) . ?
C6 C11 1.398(2) . ?
C7 C8 1.375(2) . ?
C7 H7 0.9300 . ?
C8 C9 1.373(2) . ?
C8 H8 0.9300 . ?
C9 C10 1.377(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.388(2) . ?
C10 H10 0.9300 . ?
C11 O3 1.3692(19) . ?
C12 O3 1.426(2) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 N2 1.472(2) . ?
C13 C14 1.503(2) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 C15 1.368(3) . ?
C14 C19 1.373(3) . ?
C15 C16 1.375(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.354(3) . ?
C16 H16 0.9300 . ?
C17 C18 1.355(3) . ?
C17 H17 0.9300 . ?
C18 C19 1.390(3) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?
N2 N3 1.3359(19) . ?
N3 N4 1.3156(19) . ?

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 C5 105.09(14) . . ?
N2 C1 N1 120.31(14) . . ?
C5 C1 N1 134.60(15) . . ?
O2 C2 O1 123.34(18) . . ?
O2 C2 N1 127.06(18) . . ?
O1 C2 N1 109.59(16) . . ?
O1 C3 C4 105.15(14) . . ?
O1 C3 H3A 110.7 . . ?
C4 C3 H3A 110.7 . . ?
O1 C3 H3B 110.7 . . ?
C4 C3 H3B 110.7 . . ?
H3A C3 H3B 108.8 . . ?
N1 C4 C3 100.62(15) . . ?
N1 C4 H4A 111.6 . . ?
C3 C4 H4A 111.6 . . ?
N1 C4 H4B 111.6 . . ?
C3 C4 H4B 111.6 . . ?
H4A C4 H4B 109.4 . . ?
N4 C5 C1 107.12(14) . . ?
N4 C5 C6 118.66(13) . . ?
C1 C5 C6 134.06(15) . . ?
C7 C6 C11 117.66(15) . . ?
C7 C6 C5 118.05(14) . . ?
C11 C6 C5 124.29(14) . . ?
C8 C7 C6 121.91(16) . . ?
C8 C7 H7 119.0 . . ?
C6 C7 H7 119.0 . . ?
C9 C8 C7 119.40(17) . . ?
C9 C8 H8 120.3 . . ?
C7 C8 H8 120.3 . . ?
C8 C9 C10 120.57(17) . . ?
C8 C9 H9 119.7 . . ?
C10 C9 H9 119.7 . . ?
C9 C10 C11 120.02(17) . . ?
C9 C10 H10 120.0 . . ?
C11 C10 H10 120.0 . . ?
O3 C11 C10 123.72(15) . . ?
O3 C11 C6 115.83(14) . . ?
C10 C11 C6 120.44(15) . . ?
O3 C12 H12A 109.5 . . ?
O3 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
O3 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N2 C13 C14 111.05(14) . . ?
N2 C13 H13A 109.4 . . ?
C14 C13 H13A 109.4 . . ?
N2 C13 H13B 109.4 . . ?
C14 C13 H13B 109.4 . . ?
H13A C13 H13B 108.0 . . ?
C15 C14 C19 118.22(19) . . ?
C15 C14 C13 120.76(17) . . ?
C19 C14 C13 121.01(18) . . ?
C14 C15 C16 121.0(2) . . ?
C14 C15 H15 119.5 . . ?
C16 C15 H15 119.5 . . ?
C17 C16 C15 120.4(2) . . ?
C17 C16 H16 119.8 . . ?
C15 C16 H16 119.8 . . ?
C16 C17 C18 119.9(2) . . ?
C16 C17 H17 120.1 . . ?
C18 C17 H17 120.1 . . ?
C17 C18 C19 120.1(2) . . ?
C17 C18 H18 120.0 . . ?
C19 C18 H18 120.0 . . ?
C14 C19 C18 120.4(2) . . ?
C14 C19 H19 119.8 . . ?
C18 C19 H19 119.8 . . ?
C2 N1 C1 120.11(14) . . ?
C2 N1 C4 110.31(15) . . ?
C1 N1 C4 122.94(14) . . ?
N3 N2 C1 111.05(13) . . ?
N3 N2 C13 118.88(14) . . ?
C1 N2 C13 129.91(15) . . ?
N4 N3 N2 106.85(13) . . ?
N3 N4 C5 109.89(13) . . ?
C2 O1 C3 109.59(15) . . ?
C11 O3 C12 117.41(14) . . ?

_refine_diff_density_max         0.168
_refine_diff_density_min         -0.129
_refine_diff_density_rms         0.027

####################################################################### 
# 
# 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_Pbca_a_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1970160'
loop_
_audit_author_name
_audit_author_address
'Dongsik Nam'
;Ulsan National Institute of Science and Technology
South Korea
;
_audit_update_record             
;
2019-12-05 deposited with the CCDC.	2020-04-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        6ea
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C28 H23 N3 S'
_chemical_formula_weight         433.55

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

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

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

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

_cell_length_a                   13.151(3)
_cell_length_b                   18.198(4)
_cell_length_c                   19.461(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4657.6(16)
_cell_formula_units_Z            8
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    5321
_cell_measurement_theta_min      3.065
_cell_measurement_theta_max      27.455

_exptl_crystal_description       Block
_exptl_crystal_colour            Brown
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.237
_exptl_crystal_F_000             1824
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.260
_exptl_crystal_size_min          0.250
_exptl_absorpt_coefficient_mu    0.159
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.960
_exptl_absorpt_correction_T_max  0.961
_exptl_absorpt_process_details   'Rigaku Rapid Auto'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'imaging plate'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            40382
_diffrn_reflns_av_unetI/netI     0.0289
_diffrn_reflns_av_R_equivalents  0.0545
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         3.065
_diffrn_reflns_theta_max         27.455
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             5321
_reflns_number_gt                3461
_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       'Rigaku Rapid Auto'
_computing_cell_refinement       'Rigaku Rapid Auto'
_computing_data_reduction        'Rigaku Rapid Auto'
_computing_structure_solution    SHELXS
_computing_structure_refinement  SHELXL
_computing_molecular_graphics    ORTEP
_computing_publication_material  CIFTAB
_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)+(0.0452P)²+1.1679P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5321
_refine_ls_number_parameters     289
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0923
_refine_ls_R_factor_gt           0.0520
_refine_ls_wR_factor_ref         0.1171
_refine_ls_wR_factor_gt          0.1038
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_restrained_S_all      1.016
_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
C1 C 0.57123(13) 0.56806(9) 0.31248(9) 0.0429(4) Uani 1 1 d . . . . .
C2 C 0.66034(14) 0.57851(9) 0.34929(9) 0.0446(4) Uani 1 1 d . . . . .
C3 C 0.72547(14) 0.64313(10) 0.36018(9) 0.0484(4) Uani 1 1 d . . . . .
C4 C 0.69665(18) 0.71347(11) 0.34245(14) 0.0756(7) Uani 1 1 d . . . . .
H4 H 0.6337 0.7212 0.3219 0.091 Uiso 1 1 calc R U . . .
C5 C 0.7600(2) 0.77269(12) 0.35487(16) 0.0879(8) Uani 1 1 d . . . . .
H5 H 0.7388 0.8197 0.3429 0.106 Uiso 1 1 calc R U . . .
C6 C 0.8521(2) 0.76324(13) 0.38413(13) 0.0762(7) Uani 1 1 d . . . . .
H6 H 0.8941 0.8034 0.3922 0.091 Uiso 1 1 calc R U . . .
C7 C 0.88298(19) 0.69368(14) 0.40185(12) 0.0746(7) Uani 1 1 d . . . . .
H7 H 0.9465 0.6867 0.4219 0.090 Uiso 1 1 calc R U . . .
C8 C 0.82032(17) 0.63408(12) 0.39012(11) 0.0626(6) Uani 1 1 d . . . . .
H8 H 0.8420 0.5873 0.4025 0.075 Uiso 1 1 calc R U . . .
C9 C 0.42141(16) 0.67745(11) 0.30851(13) 0.0694(6) Uani 1 1 d . . . . .
H9A H 0.4640 0.7102 0.3353 0.083 Uiso 1 1 calc R U . . .
H9B H 0.3788 0.7076 0.2792 0.083 Uiso 1 1 calc R U . . .
C10 C 0.3726(2) 0.63451(13) 0.42619(13) 0.0802(7) Uani 1 1 d . . . . .
H10 H 0.4279 0.6601 0.4438 0.096 Uiso 1 1 calc R U . . .
C11 C 0.3095(3) 0.59596(16) 0.47022(14) 0.1042(11) Uani 1 1 d . . . . .
H11 H 0.3223 0.5961 0.5172 0.125 Uiso 1 1 calc R U . . .
C12 C 0.2286(3) 0.55769(16) 0.44478(18) 0.1026(10) Uani 1 1 d . . . . .
H12 H 0.1869 0.5311 0.4743 0.123 Uiso 1 1 calc R U . . .
C13 C 0.20899(19) 0.55847(14) 0.37612(16) 0.0825(7) Uani 1 1 d . . . . .
H13 H 0.1533 0.5331 0.3587 0.099 Uiso 1 1 calc R U . . .
C14 C 0.27138(16) 0.59673(12) 0.33276(12) 0.0623(5) Uani 1 1 d . . . . .
H14 H 0.2575 0.5967 0.2859 0.075 Uiso 1 1 calc R U . . .
C15 C 0.35431(15) 0.63531(10) 0.35676(11) 0.0542(5) Uani 1 1 d . . . . .
C16 C 0.46442(13) 0.45258(9) 0.29262(9) 0.0442(4) Uani 1 1 d . . . . .
H16 H 0.4078 0.4867 0.2851 0.053 Uiso 1 1 calc R U . . .
C17 C 0.42675(13) 0.39468(9) 0.34310(10) 0.0446(4) Uani 1 1 d . . . . .
C18 C 0.40476(16) 0.41423(12) 0.40990(11) 0.0609(5) Uani 1 1 d . . . . .
H18 H 0.4152 0.4624 0.4242 0.073 Uiso 1 1 calc R U . . .
C19 C 0.36759(17) 0.36332(14) 0.45561(12) 0.0726(6) Uani 1 1 d . . . . .
H19 H 0.3534 0.3774 0.5005 0.087 Uiso 1 1 calc R U . . .
C20 C 0.35124(16) 0.29214(13) 0.43579(13) 0.0721(6) Uani 1 1 d . . . . .
H20 H 0.3267 0.2578 0.4670 0.086 Uiso 1 1 calc R U . . .
C21 C 0.37143(16) 0.27219(11) 0.36956(13) 0.0672(6) Uani 1 1 d . . . . .
H21 H 0.3596 0.2241 0.3555 0.081 Uiso 1 1 calc R U . . .
C22 C 0.40929(14) 0.32289(10) 0.32329(11) 0.0538(5) Uani 1 1 d . . . . .
H22 H 0.4231 0.3085 0.2784 0.065 Uiso 1 1 calc R U . . .
C23 C 0.49608(14) 0.42468(9) 0.22267(10) 0.0482(4) Uani 1 1 d . . . . .
C24 C 0.58891(16) 0.39137(11) 0.21249(11) 0.0608(5) Uani 1 1 d . . . . .
H24 H 0.6331 0.3859 0.2494 0.073 Uiso 1 1 calc R U . . .
C25 C 0.6174(2) 0.36608(13) 0.14881(14) 0.0823(7) Uani 1 1 d . . . . .
H25 H 0.6806 0.3439 0.1430 0.099 Uiso 1 1 calc R U . . .
C26 C 0.5543(3) 0.37332(17) 0.09481(14) 0.1003(9) Uani 1 1 d . . . . .
H26 H 0.5740 0.3566 0.0517 0.120 Uiso 1 1 calc R U . . .
C27 C 0.4610(3) 0.4053(2) 0.10340(14) 0.1074(10) Uani 1 1 d . . . . .
H27 H 0.4169 0.4093 0.0662 0.129 Uiso 1 1 calc R U . . .
C28 C 0.43156(18) 0.43194(14) 0.16796(12) 0.0760(7) Uani 1 1 d . . . . .
H28 H 0.3686 0.4544 0.1736 0.091 Uiso 1 1 calc R U . . .
N1 N 0.54762(11) 0.49581(7) 0.32351(7) 0.0439(3) Uani 1 1 d . . . . .
N2 N 0.61759(12) 0.46328(8) 0.36323(8) 0.0522(4) Uani 1 1 d . . . . .
N3 N 0.68566(12) 0.51327(8) 0.37948(8) 0.0520(4) Uani 1 1 d . . . . .
S1 S 0.50306(4) 0.62124(3) 0.25411(3) 0.05766(16) 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 N1 1.368(2) . ?
C1 C2 1.387(2) . ?
C1 S1 1.7409(17) . ?
C2 N3 1.366(2) . ?
C2 C3 1.470(2) . ?
C3 C4 1.379(3) . ?
C3 C8 1.387(3) . ?
C4 C5 1.384(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.349(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.374(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.381(3) . ?
C7 H7 0.9300 . ?
C8 H8 0.9300 . ?
C9 C15 1.499(3) . ?
C9 S1 1.822(2) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C15 1.372(3) . ?
C10 C11 1.384(4) . ?
C10 H10 0.9300 . ?
C11 C12 1.365(4) . ?
C11 H11 0.9300 . ?
C12 C13 1.361(4) . ?
C12 H12 0.9300 . ?
C13 C14 1.368(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.379(3) . ?
C14 H14 0.9300 . ?
C16 N1 1.476(2) . ?
C16 C23 1.511(3) . ?
C16 C17 1.523(2) . ?
C16 H16 0.9800 . ?
C17 C18 1.378(3) . ?
C17 C22 1.381(2) . ?
C18 C19 1.374(3) . ?
C18 H18 0.9300 . ?
C19 C20 1.369(3) . ?
C19 H19 0.9300 . ?
C20 C21 1.365(3) . ?
C20 H20 0.9300 . ?
C21 C22 1.382(3) . ?
C21 H21 0.9300 . ?
C22 H22 0.9300 . ?
C23 C28 1.368(3) . ?
C23 C24 1.377(3) . ?
C24 C25 1.374(3) . ?
C24 H24 0.9300 . ?
C25 C26 1.346(4) . ?
C25 H25 0.9300 . ?
C26 C27 1.368(4) . ?
C26 H26 0.9300 . ?
C27 C28 1.402(4) . ?
C27 H27 0.9300 . ?
C28 H28 0.9300 . ?
N1 N2 1.340(2) . ?
N2 N3 1.315(2) . ?

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 104.04(14) . . ?
N1 C1 S1 121.33(13) . . ?
C2 C1 S1 134.11(13) . . ?
N3 C2 C1 108.01(15) . . ?
N3 C2 C3 119.42(16) . . ?
C1 C2 C3 132.58(16) . . ?
C4 C3 C8 117.56(18) . . ?
C4 C3 C2 123.12(19) . . ?
C8 C3 C2 119.32(17) . . ?
C3 C4 C5 120.9(2) . . ?
C3 C4 H4 119.5 . . ?
C5 C4 H4 119.5 . . ?
C6 C5 C4 121.0(2) . . ?
C6 C5 H5 119.5 . . ?
C4 C5 H5 119.5 . . ?
C5 C6 C7 119.3(2) . . ?
C5 C6 H6 120.4 . . ?
C7 C6 H6 120.4 . . ?
C6 C7 C8 120.4(2) . . ?
C6 C7 H7 119.8 . . ?
C8 C7 H7 119.8 . . ?
C7 C8 C3 120.9(2) . . ?
C7 C8 H8 119.6 . . ?
C3 C8 H8 119.6 . . ?
C15 C9 S1 115.06(14) . . ?
C15 C9 H9A 108.5 . . ?
S1 C9 H9A 108.5 . . ?
C15 C9 H9B 108.5 . . ?
S1 C9 H9B 108.5 . . ?
H9A C9 H9B 107.5 . . ?
C15 C10 C11 120.7(3) . . ?
C15 C10 H10 119.7 . . ?
C11 C10 H10 119.7 . . ?
C12 C11 C10 120.1(3) . . ?
C12 C11 H11 119.9 . . ?
C10 C11 H11 119.9 . . ?
C13 C12 C11 119.9(3) . . ?
C13 C12 H12 120.1 . . ?
C11 C12 H12 120.1 . . ?
C12 C13 C14 119.9(3) . . ?
C12 C13 H13 120.1 . . ?
C14 C13 H13 120.1 . . ?
C13 C14 C15 121.7(2) . . ?
C13 C14 H14 119.2 . . ?
C15 C14 H14 119.2 . . ?
C10 C15 C14 117.8(2) . . ?
C10 C15 C9 121.3(2) . . ?
C14 C15 C9 120.9(2) . . ?
N1 C16 C23 109.98(14) . . ?
N1 C16 C17 110.31(14) . . ?
C23 C16 C17 115.98(14) . . ?
N1 C16 H16 106.7 . . ?
C23 C16 H16 106.7 . . ?
C17 C16 H16 106.7 . . ?
C18 C17 C22 118.19(18) . . ?
C18 C17 C16 119.86(16) . . ?
C22 C17 C16 121.89(17) . . ?
C19 C18 C17 120.7(2) . . ?
C19 C18 H18 119.6 . . ?
C17 C18 H18 119.6 . . ?
C20 C19 C18 120.8(2) . . ?
C20 C19 H19 119.6 . . ?
C18 C19 H19 119.6 . . ?
C21 C20 C19 119.2(2) . . ?
C21 C20 H20 120.4 . . ?
C19 C20 H20 120.4 . . ?
C20 C21 C22 120.5(2) . . ?
C20 C21 H21 119.7 . . ?
C22 C21 H21 119.7 . . ?
C17 C22 C21 120.6(2) . . ?
C17 C22 H22 119.7 . . ?
C21 C22 H22 119.7 . . ?
C28 C23 C24 118.7(2) . . ?
C28 C23 C16 119.84(18) . . ?
C24 C23 C16 121.44(17) . . ?
C25 C24 C23 121.3(2) . . ?
C25 C24 H24 119.4 . . ?
C23 C24 H24 119.4 . . ?
C26 C25 C24 120.2(3) . . ?
C26 C25 H25 119.9 . . ?
C24 C25 H25 119.9 . . ?
C25 C26 C27 120.0(3) . . ?
C25 C26 H26 120.0 . . ?
C27 C26 H26 120.0 . . ?
C26 C27 C28 120.3(3) . . ?
C26 C27 H27 119.8 . . ?
C28 C27 H27 119.8 . . ?
C23 C28 C27 119.5(2) . . ?
C23 C28 H28 120.2 . . ?
C27 C28 H28 120.2 . . ?
N2 N1 C1 111.06(14) . . ?
N2 N1 C16 120.59(13) . . ?
C1 N1 C16 128.08(14) . . ?
N3 N2 N1 107.51(13) . . ?
N2 N3 C2 109.38(14) . . ?
C1 S1 C9 103.68(10) . . ?

_refine_diff_density_max         0.204
_refine_diff_density_min         -0.198
_refine_diff_density_rms         0.030

