# Electronic Supplementary Material (ESI) for Green 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_846_lsf_0m
_database_code_depnum_ccdc_archive 'CCDC 2165779'
loop_
_audit_author_name
_audit_author_address
'Sifeng Li'
;Shenzhen Polytechnic
China
;
_audit_update_record             
;
2022-04-11 deposited with the CCDC.	2022-10-31 downloaded from the CCDC.
;
_audit_creation_date             2021-11-30
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.02.04 svn.rd84adfe8 for OlexSys, GUI svn.r6032)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H17 N3 S'
_chemical_formula_sum            'C19 H17 N3 S'
_chemical_formula_weight         319.41
_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 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.3612(2)
_cell_length_b                   9.7442(2)
_cell_length_c                   10.6475(2)
_cell_angle_alpha                65.8180(10)
_cell_angle_beta                 86.3210(10)
_cell_angle_gamma                79.4170(10)
_cell_volume                     777.84(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    6127
_cell_measurement_temperature    200.0
_cell_measurement_theta_max      68.192
_cell_measurement_theta_min      4.553
_shelx_estimated_absorpt_T_max   0.866
_shelx_estimated_absorpt_T_min   0.708
_exptl_absorpt_coefficient_mu    1.853
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.6475
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1085 before and 0.0694 after correction.
The Ratio of minimum to maximum transmission is 0.8598.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.364
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             336
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0474
_diffrn_reflns_av_unetI/netI     0.0410
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            10004
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.186
_diffrn_reflns_theta_min         4.552
_diffrn_ambient_temperature      200.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2607
_reflns_number_total             2825
_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 V8.38A (Bruker, 2018)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2017/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.287
_refine_diff_density_min         -0.285
_refine_diff_density_rms         0.045
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.099
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     324
_refine_ls_number_reflns         2825
_refine_ls_number_restraints     872
_refine_ls_R_factor_all          0.0503
_refine_ls_R_factor_gt           0.0466
_refine_ls_restrained_S_all      0.994
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0515P)²+0.3640P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1197
_refine_ls_wR_factor_ref         0.1229
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 S1A-C12A \\sim S1A-C9A \\sim S1B-C9B \\sim S1B-C12B
 with sigma of 0.02
 C9B-C10B \\sim C11B-C12B \\sim C12A-C11A \\sim C10A-C9A
 with sigma of 0.02
 C10B-C11B \\sim C10A-C11A
 with sigma of 0.02
 S1B-C11B \\sim S1B-C10B
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
All non-hydrogen atoms have similar U: within 2A with sigma of 0.01 and sigma
for terminal atoms of 0.02 within 2A
4. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.02
5. Others
 Sof(S1B)=Sof(N2B)=Sof(C19B)=Sof(C18B)=Sof(H18B)=Sof(C17B)=Sof(H17B)=Sof(C16B)=
 Sof(H16B)=Sof(C15B)=Sof(H15B)=Sof(N3B)=Sof(H8BD)=Sof(H8BC)=Sof(C9B)=Sof(H9B)=
 Sof(C10B)=Sof(H10B)=Sof(C11B)=Sof(H11B)=Sof(C12B)=Sof(C13B)=Sof(C14B)=1-FVAR(1)
 Sof(S1A)=Sof(H8AB)=Sof(H8AA)=Sof(N2A)=Sof(N3A)=Sof(C9A)=Sof(H9A)=Sof(C10A)=
 Sof(H10A)=Sof(C11A)=Sof(H11A)=Sof(C12A)=Sof(C13A)=Sof(C14A)=Sof(C15A)=
 Sof(H15A)=Sof(C16A)=Sof(H16A)=Sof(C17A)=Sof(H17A)=Sof(C18A)=Sof(H18A)=
 Sof(C19A)=FVAR(1)
6.a Secondary CH2 refined with riding coordinates:
 C8(H8AB,H8AA), C8(H8BD,H8BC)
6.b Aromatic/amide H refined with riding coordinates:
 C18B(H18B), C17B(H17B), C16B(H16B), C15B(H15B), C2(H2), C3(H3), C4(H4),
 C5(H5), C6(H6), C9B(H9B), C10B(H10B), C11B(H11B), C9A(H9A), C10A(H10A),
 C11A(H11A), C15A(H15A), C16A(H16A), C17A(H17A), C18A(H18A)
6.c Fitted hexagon refined as free rotating group:
 N2B(C19B,C18B,C17B,C16B,C15B)
6.d Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C)
;
_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
S1A S 0.69531(9) 0.20653(11) 0.12814(7) 0.0458(2) Uani 0.850(2) 1 d D U P A 1
S1B S 0.857(2) 0.010(2) 0.6337(12) 0.0526(18) Uani 0.150(2) 1 d D U P A 2
N1 N 0.2830(2) 0.38153(17) 0.53166(17) 0.0378(4) Uani 1 1 d . U . . .
N2B N 0.4745(13) 0.2546(12) 0.2662(9) 0.032(2) Uani 0.150(2) 1 d G U P A 2
C19B C 0.6296(12) 0.2018(12) 0.2315(10) 0.035(2) Uani 0.150(2) 1 d G U P A 2
C18B C 0.6637(17) 0.223(2) 0.0960(13) 0.051(3) Uani 0.150(2) 1 d G U P A 2
H18B H 0.769764 0.186755 0.072255 0.061 Uiso 0.150(2) 1 calc R U P A 2
C17B C 0.543(2) 0.297(4) -0.0049(10) 0.044(3) Uani 0.150(2) 1 d G U P A 2
H17B H 0.566118 0.310847 -0.097470 0.053 Uiso 0.150(2) 1 calc R U P A 2
C16B C 0.388(2) 0.349(4) 0.0298(13) 0.039(3) Uani 0.150(2) 1 d G U P A 2
H16B H 0.304969 0.399646 -0.039076 0.047 Uiso 0.150(2) 1 calc R U P A 2
C15B C 0.3535(14) 0.328(2) 0.1653(15) 0.032(3) Uani 0.150(2) 1 d G U P A 2
H15B H 0.247465 0.364353 0.189044 0.038 Uiso 0.150(2) 1 calc R U P A 2
N3B N 0.7220(18) 0.1295(16) 0.3636(15) 0.035(2) Uani 0.150(2) 1 d . U P A 2
C1 C 0.1823(2) 0.3909(2) 0.63777(19) 0.0336(4) Uani 1 1 d . U . . .
C2 C 0.1167(2) 0.2662(2) 0.7341(2) 0.0399(4) Uani 1 1 d . U . . .
H2 H 0.135767 0.171973 0.724209 0.048 Uiso 1 1 calc R U . . .
C3 C 0.0251(3) 0.2785(3) 0.8429(2) 0.0462(5) Uani 1 1 d . U . . .
H3 H -0.016951 0.192204 0.906673 0.055 Uiso 1 1 calc R U . . .
C4 C -0.0067(3) 0.4131(3) 0.8611(2) 0.0502(5) Uani 1 1 d . U . . .
H4 H -0.069074 0.420216 0.936624 0.060 Uiso 1 1 calc R U . . .
C5 C 0.0546(3) 0.5368(3) 0.7667(2) 0.0495(5) Uani 1 1 d . U . . .
H5 H 0.033603 0.630528 0.777464 0.059 Uiso 1 1 calc R U . . .
C6 C 0.1457(2) 0.5280(2) 0.6566(2) 0.0420(5) Uani 1 1 d . U . . .
H6 H 0.184529 0.616077 0.592430 0.050 Uiso 1 1 calc R U . . .
C7 C 0.3157(3) 0.5209(2) 0.4195(2) 0.0441(5) Uani 1 1 d . U . . .
H7A H 0.388853 0.495013 0.353777 0.066 Uiso 1 1 calc R U . . .
H7B H 0.366935 0.579714 0.456227 0.066 Uiso 1 1 calc R U . . .
H7C H 0.213250 0.582096 0.372720 0.066 Uiso 1 1 calc R U . . .
C8 C 0.3053(2) 0.2494(2) 0.4968(2) 0.0367(4) Uani 1 1 d . U . . .
H8AB H 0.250357 0.278205 0.407656 0.044 Uiso 0.850(2) 1 calc R U P A 1
H8AA H 0.254781 0.167350 0.568094 0.044 Uiso 0.850(2) 1 calc R U P A 1
H8BD H 0.208463 0.259174 0.442873 0.044 Uiso 0.150(2) 1 calc R U P A 2
H8BC H 0.305479 0.157590 0.583806 0.044 Uiso 0.150(2) 1 calc R U P A 2
C9B C 0.846(5) -0.051(4) 0.806(2) 0.046(3) Uani 0.150(2) 1 d D U P A 2
H9B H 0.929970 -0.114465 0.870192 0.055 Uiso 0.150(2) 1 calc R U P A 2
C10B C 0.694(5) 0.009(6) 0.836(2) 0.039(3) Uani 0.150(2) 1 d D U P A 2
H10B H 0.661909 -0.004140 0.927146 0.047 Uiso 0.150(2) 1 calc R U P A 2
C11B C 0.586(3) 0.092(3) 0.719(2) 0.029(3) Uani 0.150(2) 1 d D U P A 2
H11B H 0.477870 0.140017 0.722824 0.034 Uiso 0.150(2) 1 calc R U P A 2
C12B C 0.662(2) 0.0918(16) 0.5980(14) 0.0300(19) Uani 0.150(2) 1 d D U P A 2
C13B C 0.6115(17) 0.1495(15) 0.4538(17) 0.0327(19) Uani 0.150(2) 1 d . U P A 2
C14B C 0.4669(17) 0.2168(15) 0.4106(17) 0.033(2) Uani 0.150(2) 1 d . U P A 2
N2A N 0.5823(3) 0.1238(2) 0.6017(2) 0.0312(4) Uani 0.850(2) 1 d . U P A 1
N3A N 0.7357(3) 0.1124(3) 0.4246(3) 0.0335(5) Uani 0.850(2) 1 d . U P A 1
C9A C 0.5744(5) 0.2900(6) -0.0121(3) 0.0463(8) Uani 0.850(2) 1 d D U P A 1
H9A H 0.609786 0.301169 -0.101804 0.056 Uiso 0.850(2) 1 calc R U P A 1
C10A C 0.4211(5) 0.3393(7) 0.0172(3) 0.0462(9) Uani 0.850(2) 1 d D U P A 1
H10A H 0.336587 0.388396 -0.050136 0.055 Uiso 0.850(2) 1 calc R U P A 1
C11A C 0.3982(4) 0.3111(4) 0.1576(3) 0.0378(7) Uani 0.850(2) 1 d D U P A 1
H11A H 0.297748 0.338846 0.195372 0.045 Uiso 0.850(2) 1 calc R U P A 1
C12A C 0.5415(4) 0.2376(3) 0.2339(3) 0.0329(5) Uani 0.850(2) 1 d D U P A 1
C13A C 0.5795(3) 0.1841(2) 0.3785(3) 0.0302(5) Uani 0.850(2) 1 d . U P A 1
C14A C 0.4810(3) 0.1921(2) 0.4869(3) 0.0309(5) Uani 0.850(2) 1 d . U P A 1
C15A C 0.5547(4) 0.1018(5) 0.7384(4) 0.0258(6) Uani 0.850(2) 1 d . U P A 1
H15A H 0.450750 0.137715 0.765786 0.031 Uiso 0.850(2) 1 calc R U P A 1
C16A C 0.6753(10) 0.0299(10) 0.8305(5) 0.0463(12) Uani 0.850(2) 1 d . U P A 1
H16A H 0.656162 0.012787 0.924294 0.056 Uiso 0.850(2) 1 calc R U P A 1
C17A C 0.8322(8) -0.0214(6) 0.7902(4) 0.0443(10) Uani 0.850(2) 1 d . U P A 1
H17A H 0.916368 -0.068915 0.857970 0.053 Uiso 0.850(2) 1 calc R U P A 1
C18A C 0.8668(13) -0.0059(13) 0.6616(8) 0.0491(15) Uani 0.850(2) 1 d . U P A 1
H18A H 0.970886 -0.045851 0.637681 0.059 Uiso 0.850(2) 1 calc R U P A 1
C19A C 0.7357(3) 0.0762(2) 0.5591(2) 0.0310(5) Uani 0.850(2) 1 d . U P A 1


_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
S1A C9A 1.676(3) . ?
S1A C12A 1.722(3) . ?
S1B C9B 1.680(17) . ?
S1B C12B 1.667(15) . ?
N1 C1 1.389(2) . ?
N1 C7 1.453(3) . ?
N1 C8 1.458(2) . ?
N2B C19B 1.3900 . ?
N2B C15B 1.3900 . ?
N2B C14B 1.427(19) . ?
C19B C18B 1.3900 . ?
C19B N3B 1.483(18) . ?
C18B H18B 0.9500 . ?
C18B C17B 1.3900 . ?
C17B H17B 0.9500 . ?
C17B C16B 1.3900 . ?
C16B H16B 0.9500 . ?
C16B C15B 1.3900 . ?
C15B H15B 0.9500 . ?
N3B C13B 1.337(19) . ?
C1 C2 1.408(3) . ?
C1 C6 1.407(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.381(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.379(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.376(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.380(3) . ?
C6 H6 0.9500 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 H8AB 0.9900 . ?
C8 H8AA 0.9900 . ?
C8 H8BD 0.9900 . ?
C8 H8BC 0.9900 . ?
C8 C14B 1.641(13) . ?
C8 C14A 1.486(3) . ?
C9B H9B 0.9500 . ?
C9B C10B 1.376(17) . ?
C10B H10B 0.9500 . ?
C10B C11B 1.44(2) . ?
C11B H11B 0.9500 . ?
C11B C12B 1.396(16) . ?
C12B C13B 1.46(2) . ?
C13B C14B 1.28(2) . ?
N2A C14A 1.383(3) . ?
N2A C15A 1.392(4) . ?
N2A C19A 1.394(3) . ?
N3A C13A 1.378(3) . ?
N3A C19A 1.327(4) . ?
C9A H9A 0.9500 . ?
C9A C10A 1.348(4) . ?
C10A H10A 0.9500 . ?
C10A C11A 1.412(4) . ?
C11A H11A 0.9500 . ?
C11A C12A 1.393(4) . ?
C12A C13A 1.445(4) . ?
C13A C14A 1.395(3) . ?
C15A H15A 0.9500 . ?
C15A C16A 1.332(6) . ?
C16A H16A 0.9500 . ?
C16A C17A 1.421(5) . ?
C17A H17A 0.9500 . ?
C17A C18A 1.333(10) . ?
C18A H18A 0.9500 . ?
C18A C19A 1.466(8) . ?

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
C9A S1A C12A 92.85(14) . . ?
C12B S1B C9B 97.4(16) . . ?
C1 N1 C7 119.47(15) . . ?
C1 N1 C8 121.85(15) . . ?
C7 N1 C8 114.24(16) . . ?
C19B N2B C15B 120.0 . . ?
C19B N2B C14B 110.1(9) . . ?
C15B N2B C14B 129.9(9) . . ?
N2B C19B N3B 104.4(9) . . ?
C18B C19B N2B 120.0 . . ?
C18B C19B N3B 135.6(9) . . ?
C19B C18B H18B 120.0 . . ?
C19B C18B C17B 120.0 . . ?
C17B C18B H18B 120.0 . . ?
C18B C17B H17B 120.0 . . ?
C18B C17B C16B 120.0 . . ?
C16B C17B H17B 120.0 . . ?
C17B C16B H16B 120.0 . . ?
C15B C16B C17B 120.0 . . ?
C15B C16B H16B 120.0 . . ?
N2B C15B H15B 120.0 . . ?
C16B C15B N2B 120.0 . . ?
C16B C15B H15B 120.0 . . ?
C13B N3B C19B 103.0(13) . . ?
N1 C1 C2 123.16(17) . . ?
N1 C1 C6 120.35(17) . . ?
C6 C1 C2 116.44(18) . . ?
C1 C2 H2 119.5 . . ?
C3 C2 C1 121.06(19) . . ?
C3 C2 H2 119.5 . . ?
C2 C3 H3 119.2 . . ?
C4 C3 C2 121.6(2) . . ?
C4 C3 H3 119.2 . . ?
C3 C4 H4 121.0 . . ?
C5 C4 C3 118.1(2) . . ?
C5 C4 H4 121.0 . . ?
C4 C5 H5 119.2 . . ?
C4 C5 C6 121.6(2) . . ?
C6 C5 H5 119.2 . . ?
C1 C6 H6 119.4 . . ?
C5 C6 C1 121.2(2) . . ?
C5 C6 H6 119.4 . . ?
N1 C7 H7A 109.5 . . ?
N1 C7 H7B 109.5 . . ?
N1 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N1 C8 H8AB 109.5 . . ?
N1 C8 H8AA 109.5 . . ?
N1 C8 H8BD 107.6 . . ?
N1 C8 H8BC 107.6 . . ?
N1 C8 C14B 119.0(5) . . ?
N1 C8 C14A 110.78(16) . . ?
H8AB C8 H8AA 108.1 . . ?
H8BD C8 H8BC 107.0 . . ?
C14B C8 H8BD 107.6 . . ?
C14B C8 H8BC 107.6 . . ?
C14A C8 H8AB 109.5 . . ?
C14A C8 H8AA 109.5 . . ?
S1B C9B H9B 126.2 . . ?
C10B C9B S1B 107.6(19) . . ?
C10B C9B H9B 126.2 . . ?
C9B C10B H10B 122.9 . . ?
C9B C10B C11B 114.2(16) . . ?
C11B C10B H10B 122.9 . . ?
C10B C11B H11B 124.3 . . ?
C12B C11B C10B 111.4(12) . . ?
C12B C11B H11B 124.3 . . ?
C11B C12B S1B 108.8(15) . . ?
C11B C12B C13B 135.1(18) . . ?
C13B C12B S1B 116.1(12) . . ?
N3B C13B C12B 118.1(14) . . ?
C14B C13B N3B 118.7(17) . . ?
C14B C13B C12B 123.2(14) . . ?
N2B C14B C8 126.5(11) . . ?
C13B C14B N2B 103.7(12) . . ?
C13B C14B C8 129.7(14) . . ?
C14A N2A C15A 131.6(2) . . ?
C14A N2A C19A 107.51(18) . . ?
C15A N2A C19A 120.9(2) . . ?
C19A N3A C13A 106.0(2) . . ?
S1A C9A H9A 123.9 . . ?
C10A C9A S1A 112.2(2) . . ?
C10A C9A H9A 123.9 . . ?
C9A C10A H10A 123.2 . . ?
C9A C10A C11A 113.5(3) . . ?
C11A C10A H10A 123.2 . . ?
C10A C11A H11A 124.2 . . ?
C12A C11A C10A 111.5(3) . . ?
C12A C11A H11A 124.2 . . ?
C11A C12A S1A 109.9(2) . . ?
C11A C12A C13A 132.4(3) . . ?
C13A C12A S1A 117.7(2) . . ?
N3A C13A C12A 118.9(2) . . ?
N3A C13A C14A 110.8(2) . . ?
C14A C13A C12A 130.3(2) . . ?
N2A C14A C8 121.7(2) . . ?
N2A C14A C13A 104.9(2) . . ?
C13A C14A C8 133.3(2) . . ?
N2A C15A H15A 120.3 . . ?
C16A C15A N2A 119.5(3) . . ?
C16A C15A H15A 120.3 . . ?
C15A C16A H16A 119.6 . . ?
C15A C16A C17A 120.7(4) . . ?
C17A C16A H16A 119.6 . . ?
C16A C17A H17A 118.5 . . ?
C18A C17A C16A 123.1(6) . . ?
C18A C17A H17A 118.5 . . ?
C17A C18A H18A 121.8 . . ?
C17A C18A C19A 116.4(9) . . ?
C19A C18A H18A 121.8 . . ?
N2A C19A C18A 119.3(5) . . ?
N3A C19A N2A 110.8(2) . . ?
N3A C19A C18A 129.9(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
S1A C9A C10A C11A 0.6(3) . . . . ?
S1A C12A C13A N3A 0.4(3) . . . . ?
S1A C12A C13A C14A -179.55(19) . . . . ?
S1B C9B C10B C11B 5(5) . . . . ?
S1B C12B C13B N3B 1.5(18) . . . . ?
S1B C12B C13B C14B -179.1(13) . . . . ?
N1 C1 C2 C3 176.04(18) . . . . ?
N1 C1 C6 C5 -175.77(19) . . . . ?
N1 C8 C14B N2B -99.5(11) . . . . ?
N1 C8 C14B C13B 82.9(14) . . . . ?
N1 C8 C14A N2A 68.5(2) . . . . ?
N1 C8 C14A C13A -114.7(3) . . . . ?
N2B C19B C18B C17B 0.0 . . . . ?
N2B C19B N3B C13B 0.0(13) . . . . ?
C19B N2B C15B C16B 0.0 . . . . ?
C19B N2B C14B C8 -176.7(9) . . . . ?
C19B N2B C14B C13B 1.4(14) . . . . ?
C19B C18B C17B C16B 0.0 . . . . ?
C19B N3B C13B C12B -179.5(11) . . . . ?
C19B N3B C13B C14B 1.0(17) . . . . ?
C18B C19B N3B C13B -179.1(13) . . . . ?
C18B C17B C16B C15B 0.0 . . . . ?
C17B C16B C15B N2B 0.0 . . . . ?
C15B N2B C19B C18B 0.0 . . . . ?
C15B N2B C19B N3B -179.3(12) . . . . ?
C15B N2B C14B C8 1.5(18) . . . . ?
C15B N2B C14B C13B 179.6(12) . . . . ?
N3B C19B C18B C17B 179.0(17) . . . . ?
N3B C13B C14B N2B -1.5(16) . . . . ?
N3B C13B C14B C8 176.5(11) . . . . ?
C1 N1 C8 C14B -159.3(7) . . . . ?
C1 N1 C8 C14A -130.3(2) . . . . ?
C1 C2 C3 C4 0.4(3) . . . . ?
C2 C1 C6 C5 2.0(3) . . . . ?
C2 C3 C4 C5 0.5(3) . . . . ?
C3 C4 C5 C6 -0.2(3) . . . . ?
C4 C5 C6 C1 -1.1(3) . . . . ?
C6 C1 C2 C3 -1.6(3) . . . . ?
C7 N1 C1 C2 166.23(19) . . . . ?
C7 N1 C1 C6 -16.2(3) . . . . ?
C7 N1 C8 C14B 44.5(7) . . . . ?
C7 N1 C8 C14A 73.5(2) . . . . ?
C8 N1 C1 C2 11.2(3) . . . . ?
C8 N1 C1 C6 -171.19(18) . . . . ?
C9B S1B C12B C11B 8(3) . . . . ?
C9B S1B C12B C13B -174(2) . . . . ?
C9B C10B C11B C12B 1(5) . . . . ?
C10B C11B C12B S1B -6(4) . . . . ?
C10B C11B C12B C13B 176(3) . . . . ?
C11B C12B C13B N3B 179(2) . . . . ?
C11B C12B C13B C14B -1(3) . . . . ?
C12B S1B C9B C10B -7(4) . . . . ?
C12B C13B C14B N2B 179.1(11) . . . . ?
C12B C13B C14B C8 -3(2) . . . . ?
C14B N2B C19B C18B 178.4(12) . . . . ?
C14B N2B C19B N3B -0.8(12) . . . . ?
C14B N2B C15B C16B -178.1(15) . . . . ?
N2A C15A C16A C17A 1.4(11) . . . . ?
N3A C13A C14A C8 -176.7(2) . . . . ?
N3A C13A C14A N2A 0.5(2) . . . . ?
C9A S1A C12A C11A 0.6(2) . . . . ?
C9A S1A C12A C13A 179.7(3) . . . . ?
C9A C10A C11A C12A -0.1(3) . . . . ?
C10A C11A C12A S1A -0.4(3) . . . . ?
C10A C11A C12A C13A -179.3(3) . . . . ?
C11A C12A C13A N3A 179.3(3) . . . . ?
C11A C12A C13A C14A -0.7(4) . . . . ?
C12A S1A C9A C10A -0.7(2) . . . . ?
C12A C13A C14A C8 3.3(4) . . . . ?
C12A C13A C14A N2A -179.6(2) . . . . ?
C13A N3A C19A N2A -0.3(3) . . . . ?
C13A N3A C19A C18A 177.8(7) . . . . ?
C14A N2A C15A C16A 179.4(6) . . . . ?
C14A N2A C19A N3A 0.6(3) . . . . ?
C14A N2A C19A C18A -177.7(6) . . . . ?
C15A N2A C14A C8 -4.5(4) . . . . ?
C15A N2A C14A C13A 178.0(3) . . . . ?
C15A N2A C19A N3A -178.2(3) . . . . ?
C15A N2A C19A C18A 3.5(7) . . . . ?
C15A C16A C17A C18A -2.2(13) . . . . ?
C16A C17A C18A C19A 3.5(15) . . . . ?
C17A C18A C19A N2A -4.1(13) . . . . ?
C17A C18A C19A N3A 178.0(6) . . . . ?
C19A N2A C14A C8 176.94(18) . . . . ?
C19A N2A C14A C13A -0.6(2) . . . . ?
C19A N2A C15A C16A -2.2(7) . . . . ?
C19A N3A C13A C12A 179.9(2) . . . . ?
C19A N3A C13A C14A -0.1(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_662_lsf_0m
_database_code_depnum_ccdc_archive 'CCDC 2165780'
loop_
_audit_author_name
_audit_author_address
'Sifeng Li'
;Shenzhen Polytechnic
China
;
_audit_update_record             
;
2022-04-11 deposited with the CCDC.	2022-10-31 downloaded from the CCDC.
;
_audit_creation_date             2021-09-09
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.02.04 svn.rd84adfe8 for OlexSys, GUI svn.r6032)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H20 Br N3'
_chemical_formula_sum            'C22 H20 Br N3'
_chemical_formula_weight         406.32
_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 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   6.3317(2)
_cell_length_b                   10.0072(3)
_cell_length_c                   29.5714(8)
_cell_angle_alpha                90
_cell_angle_beta                 92.360(2)
_cell_angle_gamma                90
_cell_volume                     1872.13(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4655
_cell_measurement_temperature    200.0
_cell_measurement_theta_max      68.046
_cell_measurement_theta_min      2.991
_shelx_estimated_absorpt_T_max   0.970
_shelx_estimated_absorpt_T_min   0.374
_exptl_absorpt_coefficient_mu    3.057
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.5635
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1153 before and 0.0784 after correction.
The Ratio of minimum to maximum transmission is 0.7482.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.442
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             832
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.01
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0655
_diffrn_reflns_av_unetI/netI     0.0561
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            14919
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.193
_diffrn_reflns_theta_min         2.991
_diffrn_ambient_temperature      200.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2719
_reflns_number_total             3421
_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 V8.38A (Bruker, 2018)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2017/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.486
_refine_diff_density_min         -0.532
_refine_diff_density_rms         0.061
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         3421
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0543
_refine_ls_R_factor_gt           0.0417
_refine_ls_restrained_S_all      1.044
_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)+(0.0552P)²+0.1673P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1057
_refine_ls_wR_factor_ref         0.1127
_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:
 C14(H14A,H14B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C10(H10), C11(H11), C12(H12), C13(H13),
 C16(H16), C17(H17), C19(H19), C20(H20)
2.c Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C), C22(H22A,H22B,H22C)
;
_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
Br1 Br 0.12151(6) 0.04151(4) 0.56554(2) 0.06105(16) Uani 1 1 d . . . . .
N1 N 0.8892(4) 0.0130(3) 0.25488(9) 0.0524(7) Uani 1 1 d . . . . .
N2 N 0.5990(4) 0.5707(2) 0.38045(7) 0.0375(5) Uani 1 1 d . . . . .
N3 N 0.2962(4) 0.5631(2) 0.41729(8) 0.0400(5) Uani 1 1 d . . . . .
C1 C 0.2068(5) 0.1681(3) 0.52189(9) 0.0432(6) Uani 1 1 d . . . . .
C2 C 0.1544(5) 0.3014(3) 0.52666(9) 0.0424(6) Uani 1 1 d . . . . .
H2 H 0.071682 0.330149 0.550918 0.051 Uiso 1 1 calc R U . . .
C3 C 0.2249(4) 0.3919(3) 0.49543(8) 0.0369(6) Uani 1 1 d . . . . .
H3 H 0.190656 0.483746 0.498549 0.044 Uiso 1 1 calc R U . . .
C4 C 0.3452(4) 0.3517(3) 0.45944(8) 0.0343(6) Uani 1 1 d . . . . .
C5 C 0.3904(4) 0.2157(3) 0.45495(9) 0.0393(6) Uani 1 1 d . . . . .
H5 H 0.470670 0.186130 0.430420 0.047 Uiso 1 1 calc R U . . .
C6 C 0.3199(5) 0.1240(3) 0.48564(10) 0.0444(7) Uani 1 1 d . . . . .
H6 H 0.348634 0.031558 0.481998 0.053 Uiso 1 1 calc R U . . .
C7 C 0.4168(4) 0.4515(3) 0.42693(8) 0.0341(6) Uani 1 1 d . . . . .
C8 C 0.6042(4) 0.4529(3) 0.40510(8) 0.0354(6) Uani 1 1 d . . . . .
C9 C 0.4091(4) 0.6344(3) 0.38930(9) 0.0401(6) Uani 1 1 d . . . . .
C10 C 0.3686(5) 0.7606(3) 0.36904(11) 0.0531(8) Uani 1 1 d . . . . .
H10 H 0.240901 0.806968 0.374163 0.064 Uiso 1 1 calc R U . . .
C11 C 0.5156(6) 0.8142(4) 0.34214(12) 0.0611(9) Uani 1 1 d . . . . .
H11 H 0.489993 0.898927 0.328518 0.073 Uiso 1 1 calc R U . . .
C12 C 0.7060(6) 0.7459(4) 0.33407(12) 0.0600(9) Uani 1 1 d . . . . .
H12 H 0.806121 0.784858 0.314958 0.072 Uiso 1 1 calc R U . . .
C13 C 0.7464(5) 0.6263(3) 0.35328(10) 0.0476(7) Uani 1 1 d . . . . .
H13 H 0.874994 0.580859 0.348141 0.057 Uiso 1 1 calc R U . . .
C14 C 0.7926(4) 0.3636(3) 0.40658(8) 0.0371(6) Uani 1 1 d . . . . .
H14A H 0.787823 0.306983 0.433975 0.045 Uiso 1 1 calc R U . . .
H14B H 0.921073 0.419775 0.409765 0.045 Uiso 1 1 calc R U . . .
C15 C 0.8138(4) 0.2728(3) 0.36566(8) 0.0315(5) Uani 1 1 d . . . . .
C16 C 0.6459(4) 0.2431(3) 0.33551(8) 0.0332(5) Uani 1 1 d . . . . .
H16 H 0.511725 0.282231 0.340018 0.040 Uiso 1 1 calc R U . . .
C17 C 0.6691(4) 0.1581(3) 0.29913(8) 0.0343(6) Uani 1 1 d . . . . .
H17 H 0.551082 0.140689 0.279111 0.041 Uiso 1 1 calc R U . . .
C18 C 0.8639(4) 0.0971(3) 0.29127(8) 0.0342(6) Uani 1 1 d . . . . .
C19 C 1.0314(4) 0.1266(3) 0.32207(9) 0.0387(6) Uani 1 1 d . . . . .
H19 H 1.165428 0.086499 0.318218 0.046 Uiso 1 1 calc R U . . .
C20 C 1.0058(4) 0.2126(3) 0.35789(8) 0.0372(6) Uani 1 1 d . . . . .
H20 H 1.123563 0.231100 0.377842 0.045 Uiso 1 1 calc R U . . .
C21 C 0.7188(6) -0.0133(4) 0.22305(11) 0.0576(9) Uani 1 1 d . . . . .
H21A H 0.609574 -0.065025 0.237751 0.086 Uiso 1 1 calc R U . . .
H21B H 0.771213 -0.064357 0.197548 0.086 Uiso 1 1 calc R U . . .
H21C H 0.658709 0.071421 0.211990 0.086 Uiso 1 1 calc R U . . .
C22 C 1.0869(5) -0.0533(3) 0.24961(11) 0.0501(7) Uani 1 1 d . . . . .
H22A H 1.197963 0.013235 0.245536 0.075 Uiso 1 1 calc R U . . .
H22B H 1.076274 -0.111866 0.223045 0.075 Uiso 1 1 calc R U . . .
H22C H 1.121688 -0.106856 0.276657 0.075 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C1 1.903(3) . ?
N1 C18 1.381(4) . ?
N1 C21 1.427(4) . ?
N1 C22 1.431(4) . ?
N2 C8 1.386(4) . ?
N2 C9 1.395(4) . ?
N2 C13 1.374(4) . ?
N3 C7 1.375(3) . ?
N3 C9 1.325(4) . ?
C1 C2 1.383(4) . ?
C1 C6 1.386(4) . ?
C2 H2 0.9500 . ?
C2 C3 1.380(4) . ?
C3 H3 0.9500 . ?
C3 C4 1.393(4) . ?
C4 C5 1.398(4) . ?
C4 C7 1.471(4) . ?
C5 H5 0.9500 . ?
C5 C6 1.378(4) . ?
C6 H6 0.9500 . ?
C7 C8 1.374(4) . ?
C8 C14 1.490(4) . ?
C9 C10 1.416(4) . ?
C10 H10 0.9500 . ?
C10 C11 1.359(5) . ?
C11 H11 0.9500 . ?
C11 C12 1.415(5) . ?
C12 H12 0.9500 . ?
C12 C13 1.345(5) . ?
C13 H13 0.9500 . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C14 C15 1.523(4) . ?
C15 C16 1.391(4) . ?
C15 C20 1.384(4) . ?
C16 H16 0.9500 . ?
C16 C17 1.384(4) . ?
C17 H17 0.9500 . ?
C17 C18 1.404(4) . ?
C18 C19 1.401(4) . ?
C19 H19 0.9500 . ?
C19 C20 1.380(4) . ?
C20 H20 0.9500 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C18 N1 C21 121.2(2) . . ?
C18 N1 C22 119.9(2) . . ?
C21 N1 C22 118.9(2) . . ?
C8 N2 C9 107.0(2) . . ?
C13 N2 C8 130.5(3) . . ?
C13 N2 C9 122.4(3) . . ?
C9 N3 C7 104.9(2) . . ?
C2 C1 Br1 119.8(2) . . ?
C2 C1 C6 121.3(3) . . ?
C6 C1 Br1 118.9(2) . . ?
C1 C2 H2 120.7 . . ?
C3 C2 C1 118.6(3) . . ?
C3 C2 H2 120.7 . . ?
C2 C3 H3 119.2 . . ?
C2 C3 C4 121.6(3) . . ?
C4 C3 H3 119.2 . . ?
C3 C4 C5 118.3(3) . . ?
C3 C4 C7 119.7(2) . . ?
C5 C4 C7 122.0(2) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 C4 120.8(3) . . ?
C6 C5 H5 119.6 . . ?
C1 C6 H6 120.3 . . ?
C5 C6 C1 119.3(3) . . ?
C5 C6 H6 120.3 . . ?
N3 C7 C4 120.2(2) . . ?
C8 C7 N3 112.2(2) . . ?
C8 C7 C4 127.5(2) . . ?
N2 C8 C14 121.8(2) . . ?
C7 C8 N2 104.7(2) . . ?
C7 C8 C14 133.3(2) . . ?
N2 C9 C10 118.1(3) . . ?
N3 C9 N2 111.2(2) . . ?
N3 C9 C10 130.7(3) . . ?
C9 C10 H10 120.6 . . ?
C11 C10 C9 118.9(3) . . ?
C11 C10 H10 120.6 . . ?
C10 C11 H11 119.4 . . ?
C10 C11 C12 121.1(3) . . ?
C12 C11 H11 119.4 . . ?
C11 C12 H12 119.8 . . ?
C13 C12 C11 120.5(3) . . ?
C13 C12 H12 119.8 . . ?
N2 C13 H13 120.5 . . ?
C12 C13 N2 119.0(3) . . ?
C12 C13 H13 120.5 . . ?
C8 C14 H14A 108.4 . . ?
C8 C14 H14B 108.4 . . ?
C8 C14 C15 115.5(2) . . ?
H14A C14 H14B 107.5 . . ?
C15 C14 H14A 108.4 . . ?
C15 C14 H14B 108.4 . . ?
C16 C15 C14 123.1(2) . . ?
C20 C15 C14 119.9(2) . . ?
C20 C15 C16 117.0(2) . . ?
C15 C16 H16 119.1 . . ?
C17 C16 C15 121.8(2) . . ?
C17 C16 H16 119.1 . . ?
C16 C17 H17 119.4 . . ?
C16 C17 C18 121.2(2) . . ?
C18 C17 H17 119.4 . . ?
N1 C18 C17 121.7(2) . . ?
N1 C18 C19 121.7(2) . . ?
C19 C18 C17 116.6(2) . . ?
C18 C19 H19 119.3 . . ?
C20 C19 C18 121.4(2) . . ?
C20 C19 H19 119.3 . . ?
C15 C20 H20 119.0 . . ?
C19 C20 C15 122.1(2) . . ?
C19 C20 H20 119.0 . . ?
N1 C21 H21A 109.5 . . ?
N1 C21 H21B 109.5 . . ?
N1 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
N1 C22 H22A 109.5 . . ?
N1 C22 H22B 109.5 . . ?
N1 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 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
Br1 C1 C2 C3 177.6(2) . . . . ?
Br1 C1 C6 C5 -177.2(2) . . . . ?
N1 C18 C19 C20 178.8(3) . . . . ?
N2 C8 C14 C15 -79.7(3) . . . . ?
N2 C9 C10 C11 -0.2(4) . . . . ?
N3 C7 C8 N2 -0.4(3) . . . . ?
N3 C7 C8 C14 174.8(3) . . . . ?
N3 C9 C10 C11 178.2(3) . . . . ?
C1 C2 C3 C4 0.5(4) . . . . ?
C2 C1 C6 C5 3.1(4) . . . . ?
C2 C3 C4 C5 1.2(4) . . . . ?
C2 C3 C4 C7 179.9(2) . . . . ?
C3 C4 C5 C6 -0.8(4) . . . . ?
C3 C4 C7 N3 -31.2(3) . . . . ?
C3 C4 C7 C8 144.9(3) . . . . ?
C4 C5 C6 C1 -1.4(4) . . . . ?
C4 C7 C8 N2 -176.8(2) . . . . ?
C4 C7 C8 C14 -1.6(5) . . . . ?
C5 C4 C7 N3 147.4(3) . . . . ?
C5 C4 C7 C8 -36.4(4) . . . . ?
C6 C1 C2 C3 -2.7(4) . . . . ?
C7 N3 C9 N2 0.5(3) . . . . ?
C7 N3 C9 C10 -178.0(3) . . . . ?
C7 C4 C5 C6 -179.4(2) . . . . ?
C7 C8 C14 C15 105.7(3) . . . . ?
C8 N2 C9 N3 -0.7(3) . . . . ?
C8 N2 C9 C10 177.9(2) . . . . ?
C8 N2 C13 C12 -177.5(3) . . . . ?
C8 C14 C15 C16 -18.6(4) . . . . ?
C8 C14 C15 C20 163.2(2) . . . . ?
C9 N2 C8 C7 0.7(3) . . . . ?
C9 N2 C8 C14 -175.3(2) . . . . ?
C9 N2 C13 C12 -0.7(4) . . . . ?
C9 N3 C7 C4 176.7(2) . . . . ?
C9 N3 C7 C8 0.0(3) . . . . ?
C9 C10 C11 C12 0.3(5) . . . . ?
C10 C11 C12 C13 -0.5(5) . . . . ?
C11 C12 C13 N2 0.7(5) . . . . ?
C13 N2 C8 C7 177.9(3) . . . . ?
C13 N2 C8 C14 1.9(4) . . . . ?
C13 N2 C9 N3 -178.2(2) . . . . ?
C13 N2 C9 C10 0.4(4) . . . . ?
C14 C15 C16 C17 -178.7(2) . . . . ?
C14 C15 C20 C19 178.1(3) . . . . ?
C15 C16 C17 C18 0.5(4) . . . . ?
C16 C15 C20 C19 -0.2(4) . . . . ?
C16 C17 C18 N1 -179.5(3) . . . . ?
C16 C17 C18 C19 0.2(4) . . . . ?
C17 C18 C19 C20 -0.8(4) . . . . ?
C18 C19 C20 C15 0.8(4) . . . . ?
C20 C15 C16 C17 -0.5(4) . . . . ?
C21 N1 C18 C17 1.3(5) . . . . ?
C21 N1 C18 C19 -178.3(3) . . . . ?
C22 N1 C18 C17 -176.3(3) . . . . ?
C22 N1 C18 C19 4.1(5) . . . . ?

_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_1132_lsf_0m
_database_code_depnum_ccdc_archive 'CCDC 2175986'
loop_
_audit_author_name
_audit_author_address
'Sifeng Li'
;Shenzhen Polytechnic
China
;
_audit_update_record             
;
2022-05-31 deposited with the CCDC.	2022-10-31 downloaded from the CCDC.
;
_audit_creation_date             2022-05-27
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H19 N3'
_chemical_formula_sum            'C21 H19 N3'
_chemical_formula_weight         313.39
_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'

_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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.365(4)
_cell_length_b                   10.655(5)
_cell_length_c                   10.809(5)
_cell_angle_alpha                115.055(14)
_cell_angle_beta                 99.780(14)
_cell_angle_gamma                98.016(15)
_cell_volume                     835.6(7)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3982
_cell_measurement_temperature    298.0
_cell_measurement_theta_max      27.689
_cell_measurement_theta_min      2.881
_shelx_estimated_absorpt_T_max   0.957
_shelx_estimated_absorpt_T_min   0.957
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6360
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1175 before and 0.0804 after correction.
The Ratio of minimum to maximum transmission is 0.8530.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.246
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             332
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.6
_exptl_crystal_size_min          0.6
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0552
_diffrn_reflns_av_unetI/netI     0.0503
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            13642
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.483
_diffrn_reflns_theta_min         2.151
_diffrn_ambient_temperature      298.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2783
_reflns_number_total             3805
_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 V8.38A (Bruker, 2018)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2017/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.149
_refine_diff_density_min         -0.140
_refine_diff_density_rms         0.030
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         3805
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0676
_refine_ls_R_factor_gt           0.0470
_refine_ls_restrained_S_all      1.033
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0563P)²+0.1179P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1198
_refine_ls_wR_factor_ref         0.1352
_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:
 C8(H8A,H8B)
2.b Aromatic/amide H refined with riding coordinates:
 C00G(H00G), C1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C12(H12), C13(H13),
 C14(H14), C15(H15), C17(H17), C18(H18), C19(H19), C20(H20)
2.c Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C)
;
_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
N1 N 0.69513(16) 0.38191(12) 0.43107(13) 0.0537(3) Uani 1 1 d . . . . .
N2 N 0.37712(15) 0.13875(12) 0.28414(12) 0.0486(3) Uani 1 1 d . . . . .
N3 N 0.23128(15) 0.11535(13) 0.07826(13) 0.0526(3) Uani 1 1 d . . . . .
C00G C 0.3613(2) 0.2818(2) -0.06069(19) 0.0696(5) Uani 1 1 d . . . . .
H00G H 0.260692 0.296707 -0.038392 0.084 Uiso 1 1 calc R U . . .
C1 C 0.8533(2) 0.55122(17) 0.66903(17) 0.0613(4) Uani 1 1 d . . . . .
H1 H 0.813377 0.623403 0.656630 0.074 Uiso 1 1 calc R U . . .
C2 C 0.9566(2) 0.5830(2) 0.79756(18) 0.0694(5) Uani 1 1 d . . . . .
H2 H 0.983519 0.675732 0.870336 0.083 Uiso 1 1 calc R U . . .
C3 C 1.0200(2) 0.4805(2) 0.81991(18) 0.0687(5) Uani 1 1 d . . . . .
H3 H 1.090599 0.502649 0.906411 0.082 Uiso 1 1 calc R U . . .
C4 C 0.9769(2) 0.3444(2) 0.71151(19) 0.0663(4) Uani 1 1 d . . . . .
H4 H 1.018381 0.273504 0.725353 0.080 Uiso 1 1 calc R U . . .
C5 C 0.87334(19) 0.31011(17) 0.58236(17) 0.0580(4) Uani 1 1 d . . . . .
H5 H 0.846930 0.216770 0.510864 0.070 Uiso 1 1 calc R U . . .
C6 C 0.80725(16) 0.41294(15) 0.55678(15) 0.0459(3) Uani 1 1 d . . . . .
C7 C 0.6608(2) 0.49890(18) 0.40247(19) 0.0689(5) Uani 1 1 d . . . . .
H7A H 0.583198 0.461066 0.311736 0.103 Uiso 1 1 calc R U . . .
H7B H 0.762829 0.553100 0.402824 0.103 Uiso 1 1 calc R U . . .
H7C H 0.613751 0.559538 0.474036 0.103 Uiso 1 1 calc R U . . .
C8 C 0.67179(19) 0.24869(17) 0.30222(16) 0.0561(4) Uani 1 1 d . . . . .
H8A H 0.716314 0.180547 0.326737 0.067 Uiso 1 1 calc R U . . .
H8B H 0.733329 0.266929 0.240806 0.067 Uiso 1 1 calc R U . . .
C9 C 0.49183(18) 0.18658(15) 0.22541(15) 0.0476(3) Uani 1 1 d . . . . .
C10 C 0.39825(18) 0.17148(15) 0.10000(15) 0.0479(3) Uani 1 1 d . . . . .
C11 C 0.22052(18) 0.09576(15) 0.19034(15) 0.0501(3) Uani 1 1 d . . . . .
C12 C 0.0804(2) 0.04216(17) 0.22587(18) 0.0602(4) Uani 1 1 d . . . . .
H12 H -0.025397 0.011171 0.164570 0.072 Uiso 1 1 calc R U . . .
C13 C 0.1023(2) 0.03652(18) 0.35078(19) 0.0674(5) Uani 1 1 d . . . . .
H13 H 0.010544 0.002116 0.375185 0.081 Uiso 1 1 calc R U . . .
C14 C 0.2622(3) 0.08216(18) 0.44365(18) 0.0673(5) Uani 1 1 d . . . . .
H14 H 0.274826 0.078083 0.528939 0.081 Uiso 1 1 calc R U . . .
C15 C 0.3977(2) 0.13190(16) 0.41008(16) 0.0591(4) Uani 1 1 d . . . . .
H15 H 0.503276 0.161059 0.471261 0.071 Uiso 1 1 calc R U . . .
C16 C 0.45522(18) 0.21344(15) -0.00240(14) 0.0487(3) Uani 1 1 d . . . . .
C17 C 0.6026(2) 0.18942(16) -0.04115(15) 0.0558(4) Uani 1 1 d . . . . .
H17 H 0.666362 0.141999 -0.004909 0.067 Uiso 1 1 calc R U . . .
C18 C 0.6557(2) 0.23510(18) -0.13291(17) 0.0630(4) Uani 1 1 d . . . . .
H18 H 0.754440 0.217876 -0.157993 0.076 Uiso 1 1 calc R U . . .
C19 C 0.5635(2) 0.3057(2) -0.18705(18) 0.0710(5) Uani 1 1 d . . . . .
H19 H 0.600528 0.338201 -0.247045 0.085 Uiso 1 1 calc R U . . .
C20 C 0.4156(3) 0.3279(3) -0.1517(2) 0.0826(6) Uani 1 1 d . . . . .
H20 H 0.351788 0.374270 -0.189274 0.099 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C6 1.3912(18) . ?
N1 C7 1.4587(19) . ?
N1 C8 1.466(2) . ?
N2 C9 1.3885(18) . ?
N2 C11 1.3935(19) . ?
N2 C15 1.3770(19) . ?
N3 C10 1.378(2) . ?
N3 C11 1.3286(19) . ?
C00G H00G 0.9300 . ?
C00G C16 1.387(2) . ?
C00G C20 1.384(2) . ?
C1 H1 0.9300 . ?
C1 C2 1.379(2) . ?
C1 C6 1.400(2) . ?
C2 H2 0.9300 . ?
C2 C3 1.370(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.370(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.379(2) . ?
C5 H5 0.9300 . ?
C5 C6 1.399(2) . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 C9 1.492(2) . ?
C9 C10 1.377(2) . ?
C10 C16 1.480(2) . ?
C11 C12 1.414(2) . ?
C12 H12 0.9300 . ?
C12 C13 1.359(2) . ?
C13 H13 0.9300 . ?
C13 C14 1.408(3) . ?
C14 H14 0.9300 . ?
C14 C15 1.354(2) . ?
C15 H15 0.9300 . ?
C16 C17 1.391(2) . ?
C17 H17 0.9300 . ?
C17 C18 1.384(2) . ?
C18 H18 0.9300 . ?
C18 C19 1.373(3) . ?
C19 H19 0.9300 . ?
C19 C20 1.378(3) . ?
C20 H20 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
C6 N1 C7 119.06(12) . . ?
C6 N1 C8 121.70(12) . . ?
C7 N1 C8 112.97(13) . . ?
C9 N2 C11 107.22(12) . . ?
C15 N2 C9 131.04(13) . . ?
C15 N2 C11 121.73(13) . . ?
C11 N3 C10 105.44(12) . . ?
C16 C00G H00G 119.7 . . ?
C20 C00G H00G 119.7 . . ?
C20 C00G C16 120.67(17) . . ?
C2 C1 H1 119.2 . . ?
C2 C1 C6 121.61(16) . . ?
C6 C1 H1 119.2 . . ?
C1 C2 H2 119.4 . . ?
C3 C2 C1 121.17(17) . . ?
C3 C2 H2 119.4 . . ?
C2 C3 H3 120.9 . . ?
C2 C3 C4 118.26(16) . . ?
C4 C3 H3 120.9 . . ?
C3 C4 H4 119.2 . . ?
C3 C4 C5 121.54(16) . . ?
C5 C4 H4 119.2 . . ?
C4 C5 H5 119.4 . . ?
C4 C5 C6 121.30(15) . . ?
C6 C5 H5 119.4 . . ?
N1 C6 C1 120.44(13) . . ?
N1 C6 C5 123.36(13) . . ?
C5 C6 C1 116.12(14) . . ?
N1 C7 H7A 109.5 . . ?
N1 C7 H7B 109.5 . . ?
N1 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N1 C8 H8A 109.3 . . ?
N1 C8 H8B 109.3 . . ?
N1 C8 C9 111.47(13) . . ?
H8A C8 H8B 108.0 . . ?
C9 C8 H8A 109.3 . . ?
C9 C8 H8B 109.3 . . ?
N2 C9 C8 121.59(13) . . ?
C10 C9 N2 104.86(13) . . ?
C10 C9 C8 133.38(13) . . ?
N3 C10 C16 120.17(12) . . ?
C9 C10 N3 111.62(13) . . ?
C9 C10 C16 128.14(13) . . ?
N2 C11 C12 118.54(14) . . ?
N3 C11 N2 110.86(13) . . ?
N3 C11 C12 130.59(14) . . ?
C11 C12 H12 120.4 . . ?
C13 C12 C11 119.14(16) . . ?
C13 C12 H12 120.4 . . ?
C12 C13 H13 119.6 . . ?
C12 C13 C14 120.78(16) . . ?
C14 C13 H13 119.6 . . ?
C13 C14 H14 119.7 . . ?
C15 C14 C13 120.68(16) . . ?
C15 C14 H14 119.7 . . ?
N2 C15 H15 120.4 . . ?
C14 C15 N2 119.11(16) . . ?
C14 C15 H15 120.4 . . ?
C00G C16 C10 119.54(14) . . ?
C00G C16 C17 118.08(14) . . ?
C17 C16 C10 122.36(13) . . ?
C16 C17 H17 119.5 . . ?
C18 C17 C16 120.92(15) . . ?
C18 C17 H17 119.5 . . ?
C17 C18 H18 119.8 . . ?
C19 C18 C17 120.34(16) . . ?
C19 C18 H18 119.8 . . ?
C18 C19 H19 120.3 . . ?
C18 C19 C20 119.36(16) . . ?
C20 C19 H19 120.3 . . ?
C00G C20 H20 119.7 . . ?
C19 C20 C00G 120.59(17) . . ?
C19 C20 H20 119.7 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C8 C9 N2 -64.59(18) . . . . ?
N1 C8 C9 C10 109.80(19) . . . . ?
N2 C9 C10 N3 -0.53(16) . . . . ?
N2 C9 C10 C16 176.42(13) . . . . ?
N2 C11 C12 C13 1.1(2) . . . . ?
N3 C10 C16 C00G 40.6(2) . . . . ?
N3 C10 C16 C17 -140.72(15) . . . . ?
N3 C11 C12 C13 -178.07(15) . . . . ?
C00G C16 C17 C18 1.4(2) . . . . ?
C1 C2 C3 C4 -0.7(3) . . . . ?
C2 C1 C6 N1 176.16(15) . . . . ?
C2 C1 C6 C5 -0.7(2) . . . . ?
C2 C3 C4 C5 0.5(3) . . . . ?
C3 C4 C5 C6 -0.3(3) . . . . ?
C4 C5 C6 N1 -176.33(15) . . . . ?
C4 C5 C6 C1 0.4(2) . . . . ?
C6 N1 C8 C9 138.30(14) . . . . ?
C6 C1 C2 C3 0.9(3) . . . . ?
C7 N1 C6 C1 16.3(2) . . . . ?
C7 N1 C6 C5 -167.10(15) . . . . ?
C7 N1 C8 C9 -69.85(17) . . . . ?
C8 N1 C6 C1 166.52(14) . . . . ?
C8 N1 C6 C5 -16.9(2) . . . . ?
C8 C9 C10 N3 -175.59(15) . . . . ?
C8 C9 C10 C16 1.4(3) . . . . ?
C9 N2 C11 N3 -0.60(16) . . . . ?
C9 N2 C11 C12 -179.92(13) . . . . ?
C9 N2 C15 C14 178.81(15) . . . . ?
C9 C10 C16 C00G -136.16(17) . . . . ?
C9 C10 C16 C17 42.6(2) . . . . ?
C10 N3 C11 N2 0.27(16) . . . . ?
C10 N3 C11 C12 179.48(15) . . . . ?
C10 C16 C17 C18 -177.39(14) . . . . ?
C11 N2 C9 C8 176.45(13) . . . . ?
C11 N2 C9 C10 0.66(15) . . . . ?
C11 N2 C15 C14 0.0(2) . . . . ?
C11 N3 C10 C9 0.17(16) . . . . ?
C11 N3 C10 C16 -177.05(13) . . . . ?
C11 C12 C13 C14 -0.5(3) . . . . ?
C12 C13 C14 C15 -0.4(3) . . . . ?
C13 C14 C15 N2 0.6(2) . . . . ?
C15 N2 C9 C8 -2.5(2) . . . . ?
C15 N2 C9 C10 -178.31(14) . . . . ?
C15 N2 C11 N3 178.49(13) . . . . ?
C15 N2 C11 C12 -0.8(2) . . . . ?
C16 C00G C20 C19 0.6(3) . . . . ?
C16 C17 C18 C19 0.2(2) . . . . ?
C17 C18 C19 C20 -1.4(3) . . . . ?
C18 C19 C20 C00G 1.0(3) . . . . ?
C20 C00G C16 C10 177.04(17) . . . . ?
C20 C00G C16 C17 -1.7(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
