# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_18mar16c_0m
_audit_block_doi                 10.5517/ccdc.csd.cc24wg5p
_database_code_depnum_ccdc_archive 'CCDC 1992592'
loop_
_audit_author_name
_audit_author_address
'chen wei'
;Dalian university of Technology
China
;
_audit_update_record             
;
2020-10-16 deposited with the CCDC.	2021-12-15 downloaded from the CCDC.
;
_audit_creation_date             2020-03-25
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         S8
_chemical_formula_sum            S8
_chemical_formula_weight         256.48
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           70
_space_group_name_H-M_alt        'F d d d'
_space_group_name_Hall           '-F 2uv 2vw'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+3/4, -y+3/4, z'
'-x+3/4, y, -z+3/4'
'x, -y+3/4, -z+3/4'
'x, y+1/2, z+1/2'
'-x+3/4, -y+5/4, z+1/2'
'-x+3/4, y+1/2, -z+5/4'
'x, -y+5/4, -z+5/4'
'x+1/2, y, z+1/2'
'-x+5/4, -y+3/4, z+1/2'
'-x+5/4, y, -z+5/4'
'x+1/2, -y+3/4, -z+5/4'
'x+1/2, y+1/2, z'
'-x+5/4, -y+5/4, z'
'-x+5/4, y+1/2, -z+3/4'
'x+1/2, -y+5/4, -z+3/4'
'-x, -y, -z'
'x-3/4, y-3/4, -z'
'x-3/4, -y, z-3/4'
'-x, y-3/4, z-3/4'
'-x, -y+1/2, -z+1/2'
'x-3/4, y-1/4, -z+1/2'
'x-3/4, -y+1/2, z-1/4'
'-x, y-1/4, z-1/4'
'-x+1/2, -y, -z+1/2'
'x-1/4, y-3/4, -z+1/2'
'x-1/4, -y, z-1/4'
'-x+1/2, y-3/4, z-1/4'
'-x+1/2, -y+1/2, -z'
'x-1/4, y-1/4, -z'
'x-1/4, -y+1/2, z-3/4'
'-x+1/2, y-1/4, z-3/4'

_cell_length_a                   10.4753(14)
_cell_length_b                   12.8737(18)
_cell_length_c                   24.510(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3305.3(8)
_cell_formula_units_Z            16
_cell_measurement_reflns_used    3393
_cell_measurement_temperature    273.15
_cell_measurement_theta_max      30.743
_cell_measurement_theta_min      2.641
_shelx_estimated_absorpt_T_max   0.820
_shelx_estimated_absorpt_T_min   0.820
_exptl_absorpt_coefficient_mu    2.060
_exptl_absorpt_correction_T_max  0.7462
_exptl_absorpt_correction_T_min  0.4510
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2012/1 (Bruker,2012) was used for absorption correction. wR2(int) was 0.1110 before and 0.0434 after correction. The Ratio of minimum to maximum transmission is 0.6044. The λ/2 correction factor is 0.0015.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.062
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             2048
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0350
_diffrn_reflns_av_unetI/netI     0.0250
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.955
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            6169
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.955
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.132
_diffrn_reflns_theta_min         2.641
_diffrn_ambient_temperature      273.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.955
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1153
_reflns_number_total             1276
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.32B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.32B (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.249
_refine_diff_density_min         -0.270
_refine_diff_density_rms         0.059
_refine_ls_extinction_coef       0.0113(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    undef
_refine_ls_matrix_type           full
_refine_ls_number_parameters     38
_refine_ls_number_reflns         1276
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0232
_refine_ls_R_factor_gt           0.0200
_refine_ls_restrained_S_all      1.063
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0232P)²+1.0306P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0484
_refine_ls_wR_factor_ref         0.0499
_refine_special_details          ?
_olex2_refinement_description    
;
;
_atom_sites_solution_hydrogens   .
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
S1 S 0.46407(3) 0.40769(3) 0.62055(2) 0.04153(11) Uani 1 1 d . . . . .
S2 S 0.39415(3) 0.45278(2) 0.79857(2) 0.04273(11) Uani 1 1 d . . . . .
S3 S 0.54278(3) 0.47983(2) 0.74594(2) 0.04315(11) Uani 1 1 d . . . . .
S4 S 0.46588(3) 0.53033(2) 0.67380(2) 0.04413(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
S1 S1 2.0472(6) 2 ?
S1 S4 2.0485(5) . ?
S2 S2 2.0425(6) 2 ?
S2 S3 2.0516(5) . ?
S3 S4 2.0490(5) . ?

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
S1 S1 S4 108.980(19) 2 . ?
S2 S2 S3 108.39(2) 2 . ?
S4 S3 S2 107.34(2) . . ?
S1 S4 S3 107.99(2) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_19jul16a_0m
_audit_block_doi                 10.5517/ccdc.csd.cc24wg3m
_database_code_depnum_ccdc_archive 'CCDC 1992590'
loop_
_audit_author_name
_audit_author_address
'chen wei'
;Dalian university of Technology
China
;
_audit_update_record             
;
2020-10-15 deposited with the CCDC.	2021-12-15 downloaded from the CCDC.
;
_audit_creation_date             2019-07-19
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C24 H30 N2 O2 Si2'
_chemical_formula_sum            'C24 H30 N2 O2 Si2'
_chemical_formula_weight         434.68
_chemical_melting_point          ?
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'
Si Si 0.0817 0.0704 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   12.0825(8)
_cell_length_b                   6.2924(4)
_cell_length_c                   15.8782(10)
_cell_angle_alpha                90
_cell_angle_beta                 90.701(4)
_cell_angle_gamma                90
_cell_volume                     1207.10(13)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    845
_cell_measurement_temperature    273.15
_cell_measurement_theta_max      19.773
_cell_measurement_theta_min      3.087
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.169
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6127
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2014/3 (Bruker,2014/3) was used for absorption correction. wR2(int) was 0.0647 before and 0.0410 after correction. The Ratio of minimum to maximum transmission is 0.8218. The λ/2 correction factor is 0.00150.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.196
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             464
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0433
_diffrn_reflns_av_unetI/netI     0.0765
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            5625
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.461
_diffrn_reflns_theta_min         1.686
_diffrn_ambient_temperature      273.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_device_type  'CCD Area Detector'
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1314
_reflns_number_total             2703
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.168
_refine_diff_density_min         -0.204
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.970
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     139
_refine_ls_number_reflns         2703
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1250
_refine_ls_R_factor_gt           0.0537
_refine_ls_restrained_S_all      0.970
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0567P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1148
_refine_ls_wR_factor_ref         0.1466
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B)
2.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C8(H8), C9(H9)
2.c Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C11(H11A,H11B,H11C), C12(H12A,H12B,H12C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
Si1 Si 0.13066(7) 0.31354(14) 0.63943(5) 0.0652(3) Uani 1 1 d . . . . .
O1 O 0.28330(16) 0.0487(4) 0.46331(14) 0.0917(8) Uani 1 1 d . . . . .
N1 N 0.33264(17) 0.3173(4) 0.55132(13) 0.0533(6) Uani 1 1 d . . . . .
C1 C 0.2222(2) 0.4140(5) 0.55256(16) 0.0615(8) Uani 1 1 d . . . . .
H1A H 0.185683 0.387270 0.498856 0.074 Uiso 1 1 calc R . . . .
H1B H 0.230381 0.566638 0.558536 0.074 Uiso 1 1 calc R . . . .
C2 C 0.3537(2) 0.1397(5) 0.50533(16) 0.0560(7) Uani 1 1 d . . . . .
C3 C 0.47480(19) 0.0850(4) 0.51885(14) 0.0447(6) Uani 1 1 d . . . . .
C4 C 0.51593(19) 0.2515(4) 0.57653(14) 0.0454(6) Uani 1 1 d . . . . .
C5 C 0.4267(2) 0.3883(4) 0.59328(15) 0.0461(6) Uani 1 1 d . . . . .
C6 C 0.4363(2) 0.5646(5) 0.64367(17) 0.0618(8) Uani 1 1 d . . . . .
H6 H 0.375848 0.652469 0.653128 0.074 Uiso 1 1 calc R . . . .
C7 C 0.5381(3) 0.6080(5) 0.67990(18) 0.0728(9) Uani 1 1 d . . . . .
H7 H 0.546824 0.726404 0.714383 0.087 Uiso 1 1 calc R . . . .
C8 C 0.6265(3) 0.4768(5) 0.6652(2) 0.0767(10) Uani 1 1 d . . . . .
H8 H 0.694561 0.507646 0.690361 0.092 Uiso 1 1 calc R . . . .
C9 C 0.6169(2) 0.3004(5) 0.61409(16) 0.0609(8) Uani 1 1 d . . . . .
H9 H 0.678120 0.214296 0.604831 0.073 Uiso 1 1 calc R . . . .
C10 C 0.1758(3) 0.4250(6) 0.74241(17) 0.0872(11) Uani 1 1 d . . . . .
H10A H 0.252438 0.391893 0.752213 0.131 Uiso 1 1 calc GR . . . .
H10B H 0.132131 0.364386 0.786440 0.131 Uiso 1 1 calc GR . . . .
H10C H 0.166181 0.576455 0.741883 0.131 Uiso 1 1 calc GR . . . .
C11 C -0.0125(2) 0.4016(7) 0.6151(2) 0.0977(12) Uani 1 1 d . . . . .
H11A H -0.013244 0.552687 0.606534 0.147 Uiso 1 1 calc GR . . . .
H11B H -0.059715 0.366061 0.661126 0.147 Uiso 1 1 calc GR . . . .
H11C H -0.038593 0.331858 0.564856 0.147 Uiso 1 1 calc GR . . . .
C12 C 0.1390(3) 0.0206(5) 0.6413(2) 0.1065(13) Uani 1 1 d . . . . .
H12A H 0.114832 -0.034866 0.587818 0.160 Uiso 1 1 calc GR . . . .
H12B H 0.092475 -0.033523 0.684863 0.160 Uiso 1 1 calc GR . . . .
H12C H 0.214174 -0.021981 0.652053 0.160 Uiso 1 1 calc GR . . . .


_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
Si1 C1 1.887(3) . ?
Si1 C10 1.855(3) . ?
Si1 C11 1.852(3) . ?
Si1 C12 1.846(4) . ?
O1 C2 1.218(3) . ?
N1 C1 1.467(3) . ?
N1 C2 1.361(3) . ?
N1 C5 1.384(3) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 C3 1.516(3) . ?
C3 C3 1.372(5) 3_656 ?
C3 C4 1.474(3) . ?
C4 C5 1.408(3) . ?
C4 C9 1.386(3) . ?
C5 C6 1.372(4) . ?
C6 H6 0.9300 . ?
C6 C7 1.378(4) . ?
C7 H7 0.9300 . ?
C7 C8 1.372(4) . ?
C8 H8 0.9300 . ?
C8 C9 1.380(4) . ?
C9 H9 0.9300 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?

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 Si1 C1 110.42(15) . . ?
C11 Si1 C1 107.51(13) . . ?
C11 Si1 C10 109.55(16) . . ?
C12 Si1 C1 108.26(15) . . ?
C12 Si1 C10 110.38(18) . . ?
C12 Si1 C11 110.67(19) . . ?
C2 N1 C1 121.6(2) . . ?
C2 N1 C5 111.4(2) . . ?
C5 N1 C1 127.0(2) . . ?
Si1 C1 H1A 108.7 . . ?
Si1 C1 H1B 108.7 . . ?
N1 C1 Si1 114.34(18) . . ?
N1 C1 H1A 108.7 . . ?
N1 C1 H1B 108.7 . . ?
H1A C1 H1B 107.6 . . ?
O1 C2 N1 123.1(2) . . ?
O1 C2 C3 129.6(3) . . ?
N1 C2 C3 107.3(2) . . ?
C3 C3 C2 123.2(3) 3_656 . ?
C3 C3 C4 132.6(3) 3_656 . ?
C4 C3 C2 104.1(2) . . ?
C5 C4 C3 107.4(2) . . ?
C9 C4 C3 135.5(2) . . ?
C9 C4 C5 117.1(2) . . ?
N1 C5 C4 109.7(2) . . ?
C6 C5 N1 127.2(2) . . ?
C6 C5 C4 123.0(2) . . ?
C5 C6 H6 120.9 . . ?
C5 C6 C7 118.2(3) . . ?
C7 C6 H6 120.9 . . ?
C6 C7 H7 119.9 . . ?
C8 C7 C6 120.2(3) . . ?
C8 C7 H7 119.9 . . ?
C7 C8 H8 119.2 . . ?
C7 C8 C9 121.6(3) . . ?
C9 C8 H8 119.2 . . ?
C4 C9 H9 120.0 . . ?
C8 C9 C4 120.0(3) . . ?
C8 C9 H9 120.0 . . ?
Si1 C10 H10A 109.5 . . ?
Si1 C10 H10B 109.5 . . ?
Si1 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
Si1 C11 H11A 109.5 . . ?
Si1 C11 H11B 109.5 . . ?
Si1 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
Si1 C12 H12A 109.5 . . ?
Si1 C12 H12B 109.5 . . ?
Si1 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 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
O1 C2 C3 C3 1.5(5) . . . 3_656 ?
O1 C2 C3 C4 -179.2(3) . . . . ?
N1 C2 C3 C3 -179.4(3) . . . 3_656 ?
N1 C2 C3 C4 -0.1(3) . . . . ?
N1 C5 C6 C7 -180.0(2) . . . . ?
C1 N1 C2 O1 -0.8(4) . . . . ?
C1 N1 C2 C3 -179.9(2) . . . . ?
C1 N1 C5 C4 179.6(2) . . . . ?
C1 N1 C5 C6 -0.9(4) . . . . ?
C2 N1 C1 Si1 91.2(3) . . . . ?
C2 N1 C5 C4 -1.0(3) . . . . ?
C2 N1 C5 C6 178.5(3) . . . . ?
C2 C3 C4 C5 -0.5(3) . . . . ?
C2 C3 C4 C9 -179.4(3) . . . . ?
C3 C3 C4 C5 178.7(3) 3_656 . . . ?
C3 C3 C4 C9 -0.1(6) 3_656 . . . ?
C3 C4 C5 N1 1.0(3) . . . . ?
C3 C4 C5 C6 -178.6(2) . . . . ?
C3 C4 C9 C8 178.7(3) . . . . ?
C4 C5 C6 C7 -0.5(4) . . . . ?
C5 N1 C1 Si1 -89.5(3) . . . . ?
C5 N1 C2 O1 179.8(3) . . . . ?
C5 N1 C2 C3 0.7(3) . . . . ?
C5 C4 C9 C8 -0.1(4) . . . . ?
C5 C6 C7 C8 0.1(4) . . . . ?
C6 C7 C8 C9 0.4(5) . . . . ?
C7 C8 C9 C4 -0.4(5) . . . . ?
C9 C4 C5 N1 -180.0(2) . . . . ?
C9 C4 C5 C6 0.5(4) . . . . ?
C10 Si1 C1 N1 74.2(2) . . . . ?
C11 Si1 C1 N1 -166.4(2) . . . . ?
C12 Si1 C1 N1 -46.8(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_19oct22a_0m_tw
_audit_block_doi                 10.5517/ccdc.csd.cc24wg4n
_database_code_depnum_ccdc_archive 'CCDC 1992591'
loop_
_audit_author_name
_audit_author_address
'chen wei'
;Dalian university of Technology
China
;
_audit_update_record             
;
2020-10-16 deposited with the CCDC.	2021-12-15 downloaded from the CCDC.
;
_audit_creation_date             2019-10-23
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H12 N4 O2'
_chemical_formula_sum            'C16 H12 N4 O2'
_chemical_formula_weight         292.30
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
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'
'-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                   22.659(3)
_cell_length_b                   8.6862(14)
_cell_length_c                   15.721(3)
_cell_angle_alpha                90
_cell_angle_beta                 121.417(9)
_cell_angle_gamma                90
_cell_volume                     2640.6(8)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    1844
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.108
_cell_measurement_theta_min      2.571
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.4750
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2012/1 (Bruker,2012) was used for absorption correction. wR2(int) was 0.1117 before and 0.0699 after correction. The Ratio of minimum to maximum transmission is 0.6370. The λ/2 correction factor is 0.0015.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.470
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1216
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_av_unetI/netI     0.0652
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            3348
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.653
_diffrn_reflns_theta_min         2.106
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2140
_reflns_number_total             3348
_reflns_special_details          
;
 _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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.32B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.32B (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    ?
_refine_diff_density_max         0.599
_refine_diff_density_min         -0.382
_refine_diff_density_rms         0.124
_refine_ls_extinction_coef       0.0040(15)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     203
_refine_ls_number_reflns         3348
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1352
_refine_ls_R_factor_gt           0.0945
_refine_ls_restrained_S_all      1.074
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1504P)²+1.6362P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2506
_refine_ls_wR_factor_ref         0.2786
_refine_special_details          
;
 Refined as a 2-component twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.609(6)
 0.391(6)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3.a Aromatic/amide H refined with riding coordinates:
 C9(H9), C10(H10), C11(H11), C13(H13), C14(H14), C15(H15)
3.b Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C16(H16A,H16B,H16C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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 0.35552(12) 0.6405(3) 0.5966(2) 0.0509(7) Uani 1 1 d . . . . .
O2 O 0.47190(14) 0.1021(3) 0.6009(2) 0.0573(8) Uani 1 1 d . . . . .
N1 N 0.29236(13) 0.4532(3) 0.6147(2) 0.0363(7) Uani 1 1 d . . . . .
N2 N 0.54641(13) 0.2910(3) 0.6141(2) 0.0357(6) Uani 1 1 d . . . . .
N3 N 0.24748(13) 0.2163(3) 0.6316(2) 0.0417(7) Uani 1 1 d . . . . .
N4 N 0.60373(13) 0.5263(4) 0.6316(2) 0.0425(7) Uani 1 1 d . . . . .
C1 C 0.34731(14) 0.5055(4) 0.6100(2) 0.0335(7) Uani 1 1 d . . . . .
C2 C 0.29501(15) 0.2938(4) 0.6254(2) 0.0331(7) Uani 1 1 d . . . . .
C3 C 0.35386(14) 0.2342(4) 0.6272(2) 0.0312(7) Uani 1 1 d . . . . .
C4 C 0.39099(14) 0.3670(3) 0.6198(2) 0.0287(6) Uani 1 1 d . . . . .
C5 C 0.45145(14) 0.3767(3) 0.6198(2) 0.0285(6) Uani 1 1 d . . . . .
C6 C 0.48853(15) 0.2378(4) 0.6114(2) 0.0339(7) Uani 1 1 d . . . . .
C7 C 0.55117(14) 0.4498(4) 0.6243(2) 0.0329(7) Uani 1 1 d . . . . .
C8 C 0.49395(14) 0.5093(3) 0.6268(2) 0.0281(6) Uani 1 1 d . . . . .
C9 C 0.49392(16) 0.6677(4) 0.6402(2) 0.0363(7) Uani 1 1 d . . . . .
H9 H 0.458716 0.715139 0.644339 0.044 Uiso 1 1 calc R . . . .
C10 C 0.54803(16) 0.7526(4) 0.6470(3) 0.0423(8) Uani 1 1 d . . . . .
H10 H 0.549177 0.858822 0.655062 0.051 Uiso 1 1 calc R . . . .
C11 C 0.60032(17) 0.6797(4) 0.6417(3) 0.0449(8) Uani 1 1 d . . . . .
H11 H 0.635410 0.740382 0.645454 0.054 Uiso 1 1 calc R . . . .
C12 C 0.59466(18) 0.1923(4) 0.6037(3) 0.0472(9) Uani 1 1 d . . . . .
H12A H 0.629627 0.155070 0.668106 0.071 Uiso 1 1 calc GR . . . .
H12B H 0.615974 0.250533 0.574905 0.071 Uiso 1 1 calc GR . . . .
H12C H 0.570007 0.106747 0.561239 0.071 Uiso 1 1 calc GR . . . .
C13 C 0.36336(17) 0.0772(4) 0.6405(3) 0.0407(8) Uani 1 1 d . . . . .
H13 H 0.401942 0.030460 0.645422 0.049 Uiso 1 1 calc R . . . .
C14 C 0.31373(18) -0.0102(4) 0.6464(3) 0.0467(9) Uani 1 1 d . . . . .
H14 H 0.318856 -0.116380 0.654583 0.056 Uiso 1 1 calc R . . . .
C15 C 0.25711(18) 0.0613(4) 0.6401(3) 0.0450(9) Uani 1 1 d . . . . .
H15 H 0.223978 0.000454 0.641841 0.054 Uiso 1 1 calc R . . . .
C16 C 0.23877(17) 0.5530(4) 0.6096(3) 0.0486(9) Uani 1 1 d . . . . .
H16A H 0.255772 0.601841 0.673043 0.073 Uiso 1 1 calc GR . . . .
H16B H 0.198675 0.492644 0.593114 0.073 Uiso 1 1 calc GR . . . .
H16C H 0.226615 0.630143 0.559415 0.073 Uiso 1 1 calc GR . . . .


_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 C1 1.222(4) . ?
O2 C6 1.222(4) . ?
N1 C1 1.364(4) . ?
N1 C2 1.392(4) . ?
N1 C16 1.460(4) . ?
N2 C6 1.370(4) . ?
N2 C7 1.387(4) . ?
N2 C12 1.464(4) . ?
N3 C2 1.317(4) . ?
N3 C15 1.359(5) . ?
N4 C7 1.315(4) . ?
N4 C11 1.349(5) . ?
C1 C4 1.514(4) . ?
C2 C3 1.417(4) . ?
C3 C4 1.468(4) . ?
C3 C13 1.379(4) . ?
C4 C5 1.373(4) . ?
C5 C6 1.515(4) . ?
C5 C8 1.468(4) . ?
C7 C8 1.416(4) . ?
C8 C9 1.392(4) . ?
C9 H9 0.9300 . ?
C9 C10 1.386(4) . ?
C10 H10 0.9300 . ?
C10 C11 1.383(5) . ?
C11 H11 0.9300 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 H13 0.9300 . ?
C13 C14 1.400(5) . ?
C14 H14 0.9300 . ?
C14 C15 1.382(5) . ?
C15 H15 0.9300 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?

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 C2 110.8(2) . . ?
C1 N1 C16 123.8(3) . . ?
C2 N1 C16 125.4(3) . . ?
C6 N2 C7 110.8(2) . . ?
C6 N2 C12 123.9(3) . . ?
C7 N2 C12 125.3(3) . . ?
C2 N3 C15 114.7(3) . . ?
C7 N4 C11 113.8(3) . . ?
O1 C1 N1 123.7(3) . . ?
O1 C1 C4 129.0(3) . . ?
N1 C1 C4 107.3(3) . . ?
N1 C2 C3 110.3(3) . . ?
N3 C2 N1 122.2(3) . . ?
N3 C2 C3 127.5(3) . . ?
C2 C3 C4 106.4(3) . . ?
C13 C3 C2 115.9(3) . . ?
C13 C3 C4 137.6(3) . . ?
C3 C4 C1 105.2(2) . . ?
C5 C4 C1 123.4(3) . . ?
C5 C4 C3 131.4(3) . . ?
C4 C5 C6 123.4(3) . . ?
C4 C5 C8 131.6(3) . . ?
C8 C5 C6 105.1(2) . . ?
O2 C6 N2 123.5(3) . . ?
O2 C6 C5 129.4(3) . . ?
N2 C6 C5 107.1(3) . . ?
N2 C7 C8 110.4(3) . . ?
N4 C7 N2 121.7(3) . . ?
N4 C7 C8 127.9(3) . . ?
C7 C8 C5 106.6(3) . . ?
C9 C8 C5 137.3(3) . . ?
C9 C8 C7 115.9(3) . . ?
C8 C9 H9 121.1 . . ?
C10 C9 C8 117.9(3) . . ?
C10 C9 H9 121.1 . . ?
C9 C10 H10 119.9 . . ?
C11 C10 C9 120.2(3) . . ?
C11 C10 H10 119.9 . . ?
N4 C11 C10 124.2(3) . . ?
N4 C11 H11 117.9 . . ?
C10 C11 H11 117.9 . . ?
N2 C12 H12A 109.5 . . ?
N2 C12 H12B 109.5 . . ?
N2 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C3 C13 H13 120.7 . . ?
C3 C13 C14 118.6(3) . . ?
C14 C13 H13 120.7 . . ?
C13 C14 H14 120.0 . . ?
C15 C14 C13 120.0(3) . . ?
C15 C14 H14 120.0 . . ?
N3 C15 C14 123.2(3) . . ?
N3 C15 H15 118.4 . . ?
C14 C15 H15 118.4 . . ?
N1 C16 H16A 109.5 . . ?
N1 C16 H16B 109.5 . . ?
N1 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C9 H9 O1 0.93 2.15 2.850(4) 131.2 . yes
C13 H13 O2 0.93 2.13 2.843(4) 132.3 . yes

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
O1 C1 C4 C3 -175.8(3) . . . . ?
O1 C1 C4 C5 3.5(5) . . . . ?
N1 C1 C4 C3 1.7(3) . . . . ?
N1 C1 C4 C5 -179.0(3) . . . . ?
N1 C2 C3 C4 1.6(3) . . . . ?
N1 C2 C3 C13 178.2(3) . . . . ?
N2 C7 C8 C5 1.2(3) . . . . ?
N2 C7 C8 C9 178.0(3) . . . . ?
N3 C2 C3 C4 -179.0(3) . . . . ?
N3 C2 C3 C13 -2.4(5) . . . . ?
N4 C7 C8 C5 -177.8(3) . . . . ?
N4 C7 C8 C9 -1.0(5) . . . . ?
C1 N1 C2 N3 -180.0(3) . . . . ?
C1 N1 C2 C3 -0.5(4) . . . . ?
C1 C4 C5 C6 -168.9(3) . . . . ?
C1 C4 C5 C8 11.0(5) . . . . ?
C2 N1 C1 O1 176.9(3) . . . . ?
C2 N1 C1 C4 -0.8(3) . . . . ?
C2 N3 C15 C14 2.8(5) . . . . ?
C2 C3 C4 C1 -1.9(3) . . . . ?
C2 C3 C4 C5 178.8(3) . . . . ?
C2 C3 C13 C14 2.8(5) . . . . ?
C3 C4 C5 C6 10.2(5) . . . . ?
C3 C4 C5 C8 -169.8(3) . . . . ?
C3 C13 C14 C15 -0.8(5) . . . . ?
C4 C3 C13 C14 178.0(3) . . . . ?
C4 C5 C6 O2 2.4(5) . . . . ?
C4 C5 C6 N2 -179.9(3) . . . . ?
C4 C5 C8 C7 179.2(3) . . . . ?
C4 C5 C8 C9 3.5(6) . . . . ?
C5 C8 C9 C10 177.1(3) . . . . ?
C6 N2 C7 N4 177.9(3) . . . . ?
C6 N2 C7 C8 -1.1(4) . . . . ?
C6 C5 C8 C7 -0.8(3) . . . . ?
C6 C5 C8 C9 -176.5(4) . . . . ?
C7 N2 C6 O2 178.5(3) . . . . ?
C7 N2 C6 C5 0.6(3) . . . . ?
C7 N4 C11 C10 1.7(5) . . . . ?
C7 C8 C9 C10 1.7(4) . . . . ?
C8 C5 C6 O2 -177.6(3) . . . . ?
C8 C5 C6 N2 0.2(3) . . . . ?
C8 C9 C10 C11 -0.8(5) . . . . ?
C9 C10 C11 N4 -1.1(5) . . . . ?
C11 N4 C7 N2 -179.6(3) . . . . ?
C11 N4 C7 C8 -0.7(5) . . . . ?
C12 N2 C6 O2 0.6(5) . . . . ?
C12 N2 C6 C5 -177.3(3) . . . . ?
C12 N2 C7 N4 -4.3(5) . . . . ?
C12 N2 C7 C8 176.7(3) . . . . ?
C13 C3 C4 C1 -177.4(4) . . . . ?
C13 C3 C4 C5 3.4(6) . . . . ?
C13 C14 C15 N3 -2.3(6) . . . . ?
C15 N3 C2 N1 179.0(3) . . . . ?
C15 N3 C2 C3 -0.4(5) . . . . ?
C16 N1 C1 O1 -3.4(5) . . . . ?
C16 N1 C1 C4 178.9(3) . . . . ?
C16 N1 C2 N3 0.3(5) . . . . ?
C16 N1 C2 C3 179.8(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.609(6)
2 0.391(6)

