# Supplementary Information (SI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2025

####################################################################### 
# 
# 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_SYC048
_database_code_depnum_ccdc_archive 'CCDC 2415277'
loop_
_audit_author_name
_audit_author_address
'Dao-Wen Luo'
;Tunghai University
Taiwan
;
_audit_update_record             
;
2025-01-08 deposited with the CCDC.	2025-07-31 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C14 H8 N2 O2'
_chemical_formula_sum            'C14 H8 N2 O2'
_chemical_melting_point          ?

_exptl_crystal_description       parallelepiped
_exptl_crystal_colour            colourless
_diffrn_ambient_temperature      150(2)
_chemical_formula_weight         236.22

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           29
_space_group_name_H-M_alt        'P c a 21'
_space_group_name_Hall           'P 2c -2ac'

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

_cell_length_a                   23.5362(16)
_cell_length_b                   5.4062(3)
_cell_length_c                   8.0446(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1023.61(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    8832
_cell_measurement_theta_min      3.067
_cell_measurement_theta_max      27.903
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.533
_exptl_crystal_F_000             488
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    0.106
_shelx_estimated_absorpt_T_min   0.967
_shelx_estimated_absorpt_T_max   0.996
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6366
_exptl_absorpt_correction_T_max  0.7456
_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            18024
_diffrn_reflns_av_unetI/netI     0.0270
_diffrn_reflns_av_R_equivalents  0.0424
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         3.462
_diffrn_reflns_theta_max         27.944
_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 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             2451
_reflns_number_gt                2343
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.864
_reflns_Friedel_fraction_max     0.996
_reflns_Friedel_fraction_full    0.997

_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    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  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)+(0.0757P)²+0.1616P] 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 1022 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.0(4)
_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_h-m   Pca2(1)
_symmetry_int_tables_number      ?
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2451
_refine_ls_number_parameters     163
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0413
_refine_ls_R_factor_gt           0.0389
_refine_ls_wR_factor_ref         0.1110
_refine_ls_wR_factor_gt          0.1087
_refine_ls_goodness_of_fit_ref   1.092
_refine_ls_restrained_S_all      1.092
_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
O1 O 0.28408(8) 0.6000(3) -0.1209(2) 0.0219(4) Uani 1 1 d . . . . .
O2 O 0.37497(8) 0.6987(4) -0.1551(2) 0.0247(4) Uani 1 1 d . . . . .
N1 N 0.33862(8) 0.0157(4) 0.1550(3) 0.0204(4) Uani 1 1 d . . . . .
N2 N 0.35337(9) 0.3634(4) 0.0071(2) 0.0183(4) Uani 1 1 d . . . . .
C1 C 0.24202(11) 0.4488(4) -0.0530(3) 0.0190(5) Uani 1 1 d . . . . .
C2 C 0.18640(11) 0.5198(5) -0.0832(3) 0.0211(5) Uani 1 1 d . . . . .
H2A H 0.178153 0.662982 -0.147259 0.025 Uiso 1 1 calc R U . . .
C3 C 0.14321(11) 0.3763(5) -0.0176(3) 0.0228(5) Uani 1 1 d . . . . .
H3A H 0.104762 0.421691 -0.036637 0.027 Uiso 1 1 calc R U . . .
C4 C 0.15539(11) 0.1653(5) 0.0765(3) 0.0223(5) Uani 1 1 d . . . . .
H4A H 0.125302 0.068347 0.120644 0.027 Uiso 1 1 calc R U . . .
C5 C 0.21110(11) 0.0977(5) 0.1052(3) 0.0209(5) Uani 1 1 d . . . . .
H5A H 0.219366 -0.045354 0.169300 0.025 Uiso 1 1 calc R U . . .
C6 C 0.25535(10) 0.2403(4) 0.0396(3) 0.0180(5) Uani 1 1 d . . . . .
C7 C 0.31468(10) 0.1910(4) 0.0699(3) 0.0178(5) Uani 1 1 d . . . . .
C8 C 0.39648(10) 0.0761(4) 0.1554(3) 0.0190(5) Uani 1 1 d . . . . .
C9 C 0.44074(10) -0.0419(5) 0.2399(3) 0.0237(5) Uani 1 1 d . . . . .
H9A H 0.434292 -0.188710 0.301912 0.028 Uiso 1 1 calc R U . . .
C10 C 0.49433(11) 0.0628(5) 0.2299(4) 0.0257(5) Uani 1 1 d . . . . .
H10A H 0.525065 -0.012655 0.287259 0.031 Uiso 1 1 calc R U . . .
C11 C 0.50413(10) 0.2779(5) 0.1369(3) 0.0262(5) Uani 1 1 d . . . . .
H11A H 0.541456 0.344512 0.133119 0.031 Uiso 1 1 calc R U . . .
C12 C 0.46098(10) 0.3967(5) 0.0501(3) 0.0223(5) Uani 1 1 d . . . . .
H12A H 0.467713 0.541128 -0.014227 0.027 Uiso 1 1 calc R U . . .
C13 C 0.40706(10) 0.2904(5) 0.0635(3) 0.0195(5) Uani 1 1 d . . . . .
C14 C 0.34020(10) 0.5635(5) -0.0934(3) 0.0194(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
O1 C14 1.354(3) . ?
O1 C1 1.395(3) . ?
O2 C14 1.204(3) . ?
N1 C7 1.297(3) . ?
N1 C8 1.400(3) . ?
N2 C14 1.385(3) . ?
N2 C7 1.398(3) . ?
N2 C13 1.400(3) . ?
C1 C2 1.386(3) . ?
C1 C6 1.387(3) . ?
C2 C3 1.384(4) . ?
C2 H2A 0.9500 . ?
C3 C4 1.398(4) . ?
C3 H3A 0.9500 . ?
C4 C5 1.381(4) . ?
C4 H4A 0.9500 . ?
C5 C6 1.399(3) . ?
C5 H5A 0.9500 . ?
C6 C7 1.442(3) . ?
C8 C9 1.397(3) . ?
C8 C13 1.397(3) . ?
C9 C10 1.385(4) . ?
C9 H9A 0.9500 . ?
C10 C11 1.402(4) . ?
C10 H10A 0.9500 . ?
C11 C12 1.390(4) . ?
C11 H11A 0.9500 . ?
C12 C13 1.397(3) . ?
C12 H12A 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
C14 O1 C1 122.88(19) . . ?
C7 N1 C8 104.7(2) . . ?
C14 N2 C7 125.9(2) . . ?
C14 N2 C13 127.7(2) . . ?
C7 N2 C13 106.41(19) . . ?
C2 C1 C6 122.2(2) . . ?
C2 C1 O1 116.1(2) . . ?
C6 C1 O1 121.7(2) . . ?
C3 C2 C1 118.2(2) . . ?
C3 C2 H2A 120.9 . . ?
C1 C2 H2A 120.9 . . ?
C2 C3 C4 120.9(2) . . ?
C2 C3 H3A 119.6 . . ?
C4 C3 H3A 119.6 . . ?
C5 C4 C3 120.1(2) . . ?
C5 C4 H4A 120.0 . . ?
C3 C4 H4A 120.0 . . ?
C4 C5 C6 119.9(2) . . ?
C4 C5 H5A 120.1 . . ?
C6 C5 H5A 120.1 . . ?
C1 C6 C5 118.8(2) . . ?
C1 C6 C7 117.4(2) . . ?
C5 C6 C7 123.7(2) . . ?
N1 C7 N2 113.3(2) . . ?
N1 C7 C6 130.1(2) . . ?
N2 C7 C6 116.5(2) . . ?
N1 C8 C9 128.3(2) . . ?
N1 C8 C13 111.4(2) . . ?
C9 C8 C13 120.2(2) . . ?
C10 C9 C8 117.7(2) . . ?
C10 C9 H9A 121.2 . . ?
C8 C9 H9A 121.2 . . ?
C9 C10 C11 121.3(2) . . ?
C9 C10 H10A 119.3 . . ?
C11 C10 H10A 119.3 . . ?
C12 C11 C10 122.1(2) . . ?
C12 C11 H11A 119.0 . . ?
C10 C11 H11A 119.0 . . ?
C11 C12 C13 115.8(2) . . ?
C11 C12 H12A 122.1 . . ?
C13 C12 H12A 122.1 . . ?
N2 C13 C12 132.8(2) . . ?
N2 C13 C8 104.2(2) . . ?
C12 C13 C8 123.0(2) . . ?
O2 C14 O1 120.5(2) . . ?
O2 C14 N2 124.2(2) . . ?
O1 C14 N2 115.3(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
C14 O1 C1 C2 175.7(2) . . . . ?
C14 O1 C1 C6 -4.1(3) . . . . ?
C6 C1 C2 C3 0.2(3) . . . . ?
O1 C1 C2 C3 -179.7(2) . . . . ?
C1 C2 C3 C4 -0.1(4) . . . . ?
C2 C3 C4 C5 0.1(4) . . . . ?
C3 C4 C5 C6 -0.2(4) . . . . ?
C2 C1 C6 C5 -0.3(3) . . . . ?
O1 C1 C6 C5 179.6(2) . . . . ?
C2 C1 C6 C7 -177.1(2) . . . . ?
O1 C1 C6 C7 2.8(3) . . . . ?
C4 C5 C6 C1 0.3(3) . . . . ?
C4 C5 C6 C7 176.8(2) . . . . ?
C8 N1 C7 N2 2.2(3) . . . . ?
C8 N1 C7 C6 -173.9(2) . . . . ?
C14 N2 C7 N1 177.2(2) . . . . ?
C13 N2 C7 N1 -1.8(3) . . . . ?
C14 N2 C7 C6 -6.1(3) . . . . ?
C13 N2 C7 C6 174.83(19) . . . . ?
C1 C6 C7 N1 177.9(2) . . . . ?
C5 C6 C7 N1 1.3(4) . . . . ?
C1 C6 C7 N2 1.9(3) . . . . ?
C5 C6 C7 N2 -174.7(2) . . . . ?
C7 N1 C8 C9 174.9(3) . . . . ?
C7 N1 C8 C13 -1.7(3) . . . . ?
N1 C8 C9 C10 -175.7(2) . . . . ?
C13 C8 C9 C10 0.7(4) . . . . ?
C8 C9 C10 C11 -0.7(4) . . . . ?
C9 C10 C11 C12 -0.1(4) . . . . ?
C10 C11 C12 C13 0.9(4) . . . . ?
C14 N2 C13 C12 5.6(4) . . . . ?
C7 N2 C13 C12 -175.4(2) . . . . ?
C14 N2 C13 C8 -178.4(2) . . . . ?
C7 N2 C13 C8 0.6(2) . . . . ?
C11 C12 C13 N2 174.3(2) . . . . ?
C11 C12 C13 C8 -1.0(4) . . . . ?
N1 C8 C13 N2 0.7(3) . . . . ?
C9 C8 C13 N2 -176.3(2) . . . . ?
N1 C8 C13 C12 177.1(2) . . . . ?
C9 C8 C13 C12 0.2(4) . . . . ?
C1 O1 C14 O2 179.9(2) . . . . ?
C1 O1 C14 N2 0.3(3) . . . . ?
C7 N2 C14 O2 -174.6(2) . . . . ?
C13 N2 C14 O2 4.3(4) . . . . ?
C7 N2 C14 O1 5.0(3) . . . . ?
C13 N2 C14 O1 -176.2(2) . . . . ?

_refine_diff_density_max         0.234
_refine_diff_density_min         -0.212
_refine_diff_density_rms         0.050

####################################################################### 
# 
# 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_SYC011
_database_code_depnum_ccdc_archive 'CCDC 2415384'
loop_
_audit_author_name
_audit_author_address
'Dao-Wen Luo'
;Tunghai University
Taiwan
;
_audit_update_record             
;
2025-01-08 deposited with the CCDC.	2025-07-31 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C10 H8 N2 O2'
_chemical_formula_sum            'C10 H8 N2 O2'
_chemical_melting_point          ?

_exptl_crystal_description       parallelepiped
_exptl_crystal_colour            colourless
_diffrn_ambient_temperature      150(2)
_chemical_formula_weight         188.18

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

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

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

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

_cell_length_a                   7.1200(8)
_cell_length_b                   10.3987(14)
_cell_length_c                   11.7591(16)
_cell_angle_alpha                90
_cell_angle_beta                 102.754(5)
_cell_angle_gamma                90
_cell_volume                     849.15(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    6493
_cell_measurement_theta_min      2.644
_cell_measurement_theta_max      27.472
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.472
_exptl_crystal_F_000             392
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.330
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.170
_exptl_absorpt_coefficient_mu    0.106
_shelx_estimated_absorpt_T_min   0.966
_shelx_estimated_absorpt_T_max   0.982
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6628
_exptl_absorpt_correction_T_max  0.7456
_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            16852
_diffrn_reflns_av_unetI/netI     0.0319
_diffrn_reflns_av_R_equivalents  0.0655
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.076
_diffrn_reflns_theta_max         27.494
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             1973
_reflns_number_gt                1609
_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. Completness statistics refer to single and 
 composite reflections containing twin component 1 only. 
;

_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    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  SHELXTL
_refine_special_details          
; 
 Refined as a 2-component twin. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.2715P)²+2.2300P] 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         1973
_refine_ls_number_parameters     128
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1286
_refine_ls_R_factor_gt           0.1116
_refine_ls_wR_factor_ref         0.4264
_refine_ls_wR_factor_gt          0.4083
_refine_ls_goodness_of_fit_ref   1.201
_refine_ls_restrained_S_all      1.201
_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
O1 O 0.6353(5) 1.0790(3) 0.3446(3) 0.0241(9) Uani 1 1 d . . . . .
O2 O 0.5744(6) 0.9393(4) 0.1992(3) 0.0308(10) Uani 1 1 d . . . . .
N1 N 0.6949(6) 0.8633(4) 0.3821(4) 0.0214(10) Uani 1 1 d . . . . .
N2 N 0.8359(6) 0.7795(4) 0.5584(4) 0.0265(11) Uani 1 1 d . . . . .
C1 C 0.7022(6) 1.1071(5) 0.4623(4) 0.0203(10) Uani 1 1 d . . . . .
C2 C 0.6907(7) 1.2350(5) 0.4930(5) 0.0244(11) Uani 1 1 d . . . . .
H2 H 0.638253 1.298024 0.436393 0.029 Uiso 1 1 calc R U . . .
C3 C 0.7584(8) 1.2682(5) 0.6093(5) 0.0289(12) Uani 1 1 d . . . . .
H3 H 0.751200 1.355157 0.632718 0.035 Uiso 1 1 calc R U . . .
C4 C 0.8367(8) 1.1756(6) 0.6924(5) 0.0297(12) Uani 1 1 d . . . . .
H4 H 0.884170 1.200181 0.771336 0.036 Uiso 1 1 calc R U . . .
C5 C 0.8455(7) 1.0480(6) 0.6599(4) 0.0260(12) Uani 1 1 d . . . . .
H5 H 0.898111 0.984855 0.716370 0.031 Uiso 1 1 calc R U . . .
C6 C 0.7761(6) 1.0128(5) 0.5431(4) 0.0194(10) Uani 1 1 d . . . . .
C7 C 0.7755(6) 0.8808(5) 0.5016(4) 0.0199(10) Uani 1 1 d . . . . .
C8 C 0.7938(8) 0.6704(5) 0.4762(5) 0.0288(12) Uani 1 1 d . . . . .
H8A H 0.699088 0.611779 0.499197 0.035 Uiso 1 1 calc R U . . .
H8B H 0.912869 0.621299 0.476144 0.035 Uiso 1 1 calc R U . . .
C9 C 0.7111(7) 0.7267(5) 0.3538(5) 0.0252(11) Uani 1 1 d . . . . .
H9A H 0.799990 0.713593 0.300913 0.030 Uiso 1 1 calc R U . . .
H9B H 0.583981 0.688966 0.318274 0.030 Uiso 1 1 calc R U . . .
C10 C 0.6320(7) 0.9560(5) 0.3027(4) 0.0216(11) 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
O1 C10 1.370(6) . ?
O1 C1 1.391(5) . ?
O2 C10 1.207(6) . ?
N1 C10 1.349(6) . ?
N1 C7 1.408(6) . ?
N1 C9 1.469(6) . ?
N2 C7 1.271(7) . ?
N2 C8 1.478(7) . ?
C1 C2 1.385(7) . ?
C1 C6 1.386(7) . ?
C2 C3 1.389(7) . ?
C2 H2 0.9500 . ?
C3 C4 1.397(8) . ?
C3 H3 0.9500 . ?
C4 C5 1.386(8) . ?
C4 H4 0.9500 . ?
C5 C6 1.402(6) . ?
C5 H5 0.9500 . ?
C6 C7 1.456(7) . ?
C8 C9 1.544(7) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?

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
C10 O1 C1 122.0(4) . . ?
C10 N1 C7 126.8(4) . . ?
C10 N1 C9 124.4(4) . . ?
C7 N1 C9 108.5(4) . . ?
C7 N2 C8 107.2(4) . . ?
C2 C1 C6 122.4(5) . . ?
C2 C1 O1 115.8(4) . . ?
C6 C1 O1 121.9(4) . . ?
C1 C2 C3 117.9(5) . . ?
C1 C2 H2 121.1 . . ?
C3 C2 H2 121.1 . . ?
C2 C3 C4 121.0(5) . . ?
C2 C3 H3 119.5 . . ?
C4 C3 H3 119.5 . . ?
C5 C4 C3 120.1(5) . . ?
C5 C4 H4 119.9 . . ?
C3 C4 H4 119.9 . . ?
C4 C5 C6 119.5(5) . . ?
C4 C5 H5 120.2 . . ?
C6 C5 H5 120.2 . . ?
C1 C6 C5 119.0(5) . . ?
C1 C6 C7 117.7(4) . . ?
C5 C6 C7 123.3(5) . . ?
N2 C7 N1 115.7(5) . . ?
N2 C7 C6 129.0(4) . . ?
N1 C7 C6 115.3(4) . . ?
N2 C8 C9 107.4(4) . . ?
N2 C8 H8A 110.2 . . ?
C9 C8 H8A 110.2 . . ?
N2 C8 H8B 110.2 . . ?
C9 C8 H8B 110.2 . . ?
H8A C8 H8B 108.5 . . ?
N1 C9 C8 100.8(4) . . ?
N1 C9 H9A 111.6 . . ?
C8 C9 H9A 111.6 . . ?
N1 C9 H9B 111.6 . . ?
C8 C9 H9B 111.6 . . ?
H9A C9 H9B 109.4 . . ?
O2 C10 N1 125.6(5) . . ?
O2 C10 O1 118.2(4) . . ?
N1 C10 O1 116.2(4) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C10 O1 C1 C2 -177.8(4) . . . . ?
C10 O1 C1 C6 2.4(7) . . . . ?
C6 C1 C2 C3 0.7(7) . . . . ?
O1 C1 C2 C3 -179.1(4) . . . . ?
C1 C2 C3 C4 0.5(8) . . . . ?
C2 C3 C4 C5 -1.0(8) . . . . ?
C3 C4 C5 C6 0.3(8) . . . . ?
C2 C1 C6 C5 -1.3(7) . . . . ?
O1 C1 C6 C5 178.5(4) . . . . ?
C2 C1 C6 C7 178.1(4) . . . . ?
O1 C1 C6 C7 -2.1(7) . . . . ?
C4 C5 C6 C1 0.8(7) . . . . ?
C4 C5 C6 C7 -178.6(4) . . . . ?
C8 N2 C7 N1 -1.7(6) . . . . ?
C8 N2 C7 C6 177.5(5) . . . . ?
C10 N1 C7 N2 -175.7(5) . . . . ?
C9 N1 C7 N2 -2.4(6) . . . . ?
C10 N1 C7 C6 4.9(7) . . . . ?
C9 N1 C7 C6 178.2(4) . . . . ?
C1 C6 C7 N2 179.5(5) . . . . ?
C5 C6 C7 N2 -1.1(8) . . . . ?
C1 C6 C7 N1 -1.2(6) . . . . ?
C5 C6 C7 N1 178.2(4) . . . . ?
C7 N2 C8 C9 5.0(5) . . . . ?
C10 N1 C9 C8 178.5(4) . . . . ?
C7 N1 C9 C8 5.1(5) . . . . ?
N2 C8 C9 N1 -6.0(5) . . . . ?
C7 N1 C10 O2 175.1(5) . . . . ?
C9 N1 C10 O2 2.9(8) . . . . ?
C7 N1 C10 O1 -4.8(7) . . . . ?
C9 N1 C10 O1 -177.0(4) . . . . ?
C1 O1 C10 O2 -179.0(4) . . . . ?
C1 O1 C10 N1 0.9(7) . . . . ?

_refine_diff_density_max         0.899
_refine_diff_density_min         -0.594
_refine_diff_density_rms         0.196

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_h-m   P2(1)/c
_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_SYC025
_database_code_depnum_ccdc_archive 'CCDC 2429895'
loop_
_audit_author_name
_audit_author_address
'Dao-Wen Luo'
;Tunghai University
Taiwan
;
_audit_update_record             
;
2025-03-10 deposited with the CCDC.	2025-07-31 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C13 H10 N2 O'
_chemical_formula_sum            'C13 H10 N2 O'
_chemical_melting_point          ?

_exptl_crystal_description       parallelepiped
_exptl_crystal_colour            colourless
_diffrn_ambient_temperature      298(2)
_chemical_formula_weight         210.23

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                   16.985(5)
_cell_length_b                   4.7953(12)
_cell_length_c                   13.075(4)
_cell_angle_alpha                90
_cell_angle_beta                 102.321(10)
_cell_angle_gamma                90
_cell_volume                     1040.4(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    6413
_cell_measurement_theta_min      2.455
_cell_measurement_theta_max      27.769
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.342
_exptl_crystal_F_000             440
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.460
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.140
_exptl_absorpt_coefficient_mu    0.087
_shelx_estimated_absorpt_T_min   0.961
_shelx_estimated_absorpt_T_max   0.988
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6370
_exptl_absorpt_correction_T_max  0.7456
_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            14113
_diffrn_reflns_av_unetI/netI     0.0590
_diffrn_reflns_av_R_equivalents  0.0638
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.587
_diffrn_reflns_theta_max         28.605
_diffrn_reflns_theta_full        26.000
_diffrn_measured_fraction_theta_max 0.910
_diffrn_measured_fraction_theta_full 0.961
_diffrn_reflns_Laue_measured_fraction_max 0.910
_diffrn_reflns_Laue_measured_fraction_full 0.961
_diffrn_reflns_point_group_measured_fraction_max 0.910
_diffrn_reflns_point_group_measured_fraction_full 0.961
_reflns_number_total             2432
_reflns_number_gt                1888
_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    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  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)+(0.1437P)²+0.2358P] 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     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.39(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2432
_refine_ls_number_parameters     154
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1191
_refine_ls_R_factor_gt           0.0785
_refine_ls_wR_factor_ref         0.2281
_refine_ls_wR_factor_gt          0.1934
_refine_ls_goodness_of_fit_ref   1.105
_refine_ls_restrained_S_all      1.105
_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
O O 0.20925(12) 0.2995(4) 0.54703(12) 0.0579(5) Uani 1 1 d . . . . .
N1 N 0.28355(10) 0.5514(4) 0.42178(13) 0.0414(5) Uani 1 1 d . . . . .
N2 N 0.25893(11) 0.4511(4) 0.25103(12) 0.0413(5) Uani 1 1 d . . . . .
H2A H 0.2367(16) 0.355(7) 0.188(2) 0.069(8) Uiso 1 1 d . . . . .
C1 C 0.16763(13) 0.1522(5) 0.46382(16) 0.0449(5) Uani 1 1 d . . . . .
C2 C 0.11050(15) -0.0402(5) 0.4802(2) 0.0582(7) Uani 1 1 d . . . . .
H2B H 0.101074 -0.064636 0.547146 0.070 Uiso 1 1 calc R U . . .
C3 C 0.06750(15) -0.1959(5) 0.3980(2) 0.0598(7) Uani 1 1 d . . . . .
H3A H 0.029612 -0.325025 0.409966 0.072 Uiso 1 1 calc R U . . .
C4 C 0.08059(14) -0.1603(5) 0.2985(2) 0.0578(6) Uani 1 1 d . . . . .
H4A H 0.051566 -0.265397 0.243356 0.069 Uiso 1 1 calc R U . . .
C5 C 0.13680(13) 0.0314(5) 0.28040(18) 0.0484(6) Uani 1 1 d . . . . .
H5A H 0.145369 0.054428 0.212992 0.058 Uiso 1 1 calc R U . . .
C6 C 0.18105(11) 0.1916(4) 0.36254(15) 0.0392(5) Uani 1 1 d . . . . .
C7 C 0.24103(11) 0.3955(4) 0.34558(14) 0.0381(5) Uani 1 1 d . . . . .
C8 C 0.33249(12) 0.7167(4) 0.37406(15) 0.0409(5) Uani 1 1 d . . . . .
C9 C 0.31735(12) 0.6549(4) 0.26685(15) 0.0407(5) Uani 1 1 d . . . . .
C10 C 0.35710(14) 0.7908(5) 0.19832(18) 0.0518(6) Uani 1 1 d . . . . .
H10A H 0.346433 0.748727 0.127257 0.062 Uiso 1 1 calc R U . . .
C11 C 0.41305(14) 0.9908(5) 0.2408(2) 0.0561(6) Uani 1 1 d . . . . .
H11A H 0.440789 1.085754 0.197408 0.067 Uiso 1 1 calc R U . . .
C12 C 0.42886(14) 1.0535(5) 0.3477(2) 0.0567(6) Uani 1 1 d . . . . .
H12A H 0.467047 1.189086 0.373755 0.068 Uiso 1 1 calc R U . . .
C13 C 0.38958(13) 0.9206(5) 0.41507(18) 0.0520(6) Uani 1 1 d . . . . .
H13A H 0.400517 0.964551 0.485979 0.062 Uiso 1 1 calc R U . . .
H0A H 0.2483(18) 0.418(8) 0.518(3) 0.087(10) Uiso 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O C1 1.362(3) . ?
O H0A 1.01(3) . ?
N1 C7 1.329(3) . ?
N1 C8 1.389(3) . ?
N2 C7 1.361(2) . ?
N2 C9 1.377(3) . ?
N2 H2A 0.95(3) . ?
C1 C2 1.388(3) . ?
C1 C6 1.404(3) . ?
C2 C3 1.382(4) . ?
C2 H2B 0.9300 . ?
C3 C4 1.377(4) . ?
C3 H3A 0.9300 . ?
C4 C5 1.382(3) . ?
C4 H4A 0.9300 . ?
C5 C6 1.401(3) . ?
C5 H5A 0.9300 . ?
C6 C7 1.463(3) . ?
C8 C13 1.401(3) . ?
C8 C9 1.402(3) . ?
C9 C10 1.393(3) . ?
C10 C11 1.380(4) . ?
C10 H10A 0.9300 . ?
C11 C12 1.399(4) . ?
C11 H11A 0.9300 . ?
C12 C13 1.370(3) . ?
C12 H12A 0.9300 . ?
C13 H13A 0.9300 . ?

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 O H0A 105(2) . . ?
C7 N1 C8 105.41(16) . . ?
C7 N2 C9 107.22(16) . . ?
C7 N2 H2A 124.4(18) . . ?
C9 N2 H2A 128.2(18) . . ?
O C1 C2 118.83(19) . . ?
O C1 C6 121.51(19) . . ?
C2 C1 C6 119.7(2) . . ?
C3 C2 C1 120.6(2) . . ?
C3 C2 H2B 119.7 . . ?
C1 C2 H2B 119.7 . . ?
C4 C3 C2 120.2(2) . . ?
C4 C3 H3A 119.9 . . ?
C2 C3 H3A 119.9 . . ?
C3 C4 C5 120.1(2) . . ?
C3 C4 H4A 120.0 . . ?
C5 C4 H4A 120.0 . . ?
C4 C5 C6 120.7(2) . . ?
C4 C5 H5A 119.6 . . ?
C6 C5 H5A 119.6 . . ?
C1 C6 C5 118.7(2) . . ?
C1 C6 C7 119.46(18) . . ?
C5 C6 C7 121.82(18) . . ?
N1 C7 N2 112.33(18) . . ?
N1 C7 C6 123.17(17) . . ?
N2 C7 C6 124.50(17) . . ?
N1 C8 C13 131.15(19) . . ?
N1 C8 C9 109.20(18) . . ?
C13 C8 C9 119.65(19) . . ?
N2 C9 C10 131.91(19) . . ?
N2 C9 C8 105.84(16) . . ?
C10 C9 C8 122.2(2) . . ?
C11 C10 C9 116.9(2) . . ?
C11 C10 H10A 121.5 . . ?
C9 C10 H10A 121.5 . . ?
C10 C11 C12 121.3(2) . . ?
C10 C11 H11A 119.3 . . ?
C12 C11 H11A 119.3 . . ?
C13 C12 C11 121.8(2) . . ?
C13 C12 H12A 119.1 . . ?
C11 C12 H12A 119.1 . . ?
C12 C13 C8 118.1(2) . . ?
C12 C13 H13A 121.0 . . ?
C8 C13 H13A 121.0 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O C1 C2 C3 -179.4(2) . . . . ?
C6 C1 C2 C3 0.9(3) . . . . ?
C1 C2 C3 C4 -0.4(4) . . . . ?
C2 C3 C4 C5 0.0(4) . . . . ?
C3 C4 C5 C6 0.0(3) . . . . ?
O C1 C6 C5 179.37(19) . . . . ?
C2 C1 C6 C5 -0.9(3) . . . . ?
O C1 C6 C7 0.0(3) . . . . ?
C2 C1 C6 C7 179.71(19) . . . . ?
C4 C5 C6 C1 0.5(3) . . . . ?
C4 C5 C6 C7 179.86(19) . . . . ?
C8 N1 C7 N2 -0.5(2) . . . . ?
C8 N1 C7 C6 -179.52(17) . . . . ?
C9 N2 C7 N1 0.5(2) . . . . ?
C9 N2 C7 C6 179.50(16) . . . . ?
C1 C6 C7 N1 -1.0(3) . . . . ?
C5 C6 C7 N1 179.61(19) . . . . ?
C1 C6 C7 N2 -179.95(18) . . . . ?
C5 C6 C7 N2 0.7(3) . . . . ?
C7 N1 C8 C13 179.8(2) . . . . ?
C7 N1 C8 C9 0.3(2) . . . . ?
C7 N2 C9 C10 -179.5(2) . . . . ?
C7 N2 C9 C8 -0.3(2) . . . . ?
N1 C8 C9 N2 0.0(2) . . . . ?
C13 C8 C9 N2 -179.61(19) . . . . ?
N1 C8 C9 C10 179.31(18) . . . . ?
C13 C8 C9 C10 -0.3(3) . . . . ?
N2 C9 C10 C11 179.4(2) . . . . ?
C8 C9 C10 C11 0.3(3) . . . . ?
C9 C10 C11 C12 0.0(3) . . . . ?
C10 C11 C12 C13 -0.2(4) . . . . ?
C11 C12 C13 C8 0.2(4) . . . . ?
N1 C8 C13 C12 -179.4(2) . . . . ?
C9 C8 C13 C12 0.1(3) . . . . ?

_refine_diff_density_max         0.576
_refine_diff_density_min         -0.712
_refine_diff_density_rms         0.198

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_h-m   P2(1)/c
_symmetry_int_tables_number      ?
_chemical_absolute_configuration ?

