# Supplementary Information (SI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 2190485'
loop_
_audit_author_name
_audit_author_address
'kun he'
;yunnan university
China
;
_audit_update_record             
;
2022-07-15 deposited with the CCDC.	2024-11-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H17 Br N2 O'
_chemical_formula_sum            'C22 H17 Br N2 O'
_chemical_formula_weight         405.28

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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

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

_cell_length_a                   13.4106(8)
_cell_length_b                   17.0023(11)
_cell_length_c                   17.4419(9)
_cell_angle_alpha                90
_cell_angle_beta                 110.493(2)
_cell_angle_gamma                90
_cell_volume                     3725.3(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    7419
_cell_measurement_theta_min      2.3958
_cell_measurement_theta_max      28.2364

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.445
_exptl_crystal_F_000             1648
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    2.220
_shelx_estimated_absorpt_T_min   0.641
_shelx_estimated_absorpt_T_max   0.691
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6507
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_special_details   
;
 The following wavelength and cell were deduced by SADABS from the
 direction cosines etc. They are given here for emergency use only:
 CELL 0.71076   13.420   17.012   17.449   89.998  110.513   89.970
;
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  graphite
_diffrn_measurement_method       'CCD area detector'
_diffrn_detector_area_resol_mean 'phi and omega scans'
_diffrn_reflns_number            29219
_diffrn_reflns_av_unetI/netI     0.0771
_diffrn_reflns_av_R_equivalents  0.0772
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.016
_diffrn_reflns_theta_max         28.369
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measured_fraction_theta_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_point_group_measured_fraction_full 0.988
_reflns_number_total             9065
_reflns_number_gt                5463
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0426P)²+1.8735P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         9065
_refine_ls_number_parameters     475
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1091
_refine_ls_R_factor_gt           0.0444
_refine_ls_wR_factor_ref         0.1236
_refine_ls_wR_factor_gt          0.0920
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_restrained_S_all      1.046
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br2 Br 0.18211(3) 0.62014(3) 0.16688(2) 0.04119(12) Uani 1 1 d . . . . .
Br1 Br 0.71315(3) 0.64917(2) 0.17767(2) 0.03819(12) Uani 1 1 d . . . . .
O1 O 0.3825(2) 0.69340(15) 0.28329(15) 0.0379(6) Uani 1 1 d . . . . .
O2 O 0.9050(2) 0.72470(15) 0.30199(15) 0.0392(6) Uani 1 1 d . . . . .
N1 N 0.0652(2) 0.57307(19) 0.27896(18) 0.0325(7) Uani 1 1 d . . . . .
N2 N 0.0014(2) 0.54727(17) 0.32034(17) 0.0296(7) Uani 1 1 d . . . . .
N3 N 0.6012(2) 0.57577(17) 0.28502(17) 0.0280(7) Uani 1 1 d . . . . .
N4 N 0.5382(2) 0.54300(17) 0.32443(16) 0.0276(6) Uani 1 1 d . . . . .
C1 C 0.4068(3) 0.7683(2) 0.5648(2) 0.0401(9) Uani 1 1 d . . . . .
H1 H 0.4273 0.7869 0.6195 0.048 Uiso 1 1 calc R U . . .
C2 C 0.3095(3) 0.7896(2) 0.5078(2) 0.0387(9) Uani 1 1 d . . . . .
H5 H 0.2641 0.8244 0.5231 0.046 Uiso 1 1 calc R U . . .
C3 C 0.2775(3) 0.7606(2) 0.4282(2) 0.0347(8) Uani 1 1 d . . . . .
H4 H 0.2095 0.7739 0.3899 0.042 Uiso 1 1 calc R U . . .
C4 C 0.3456(3) 0.7118(2) 0.4049(2) 0.0304(8) Uani 1 1 d . . . . .
C5 C 0.3178(3) 0.6840(2) 0.3178(2) 0.0310(8) Uani 1 1 d . . . . .
C6 C 0.2166(3) 0.6457(2) 0.2791(2) 0.0298(8) Uani 1 1 d . . . . .
C7 C 0.1509(3) 0.6180(2) 0.3164(2) 0.0291(8) Uani 1 1 d . . . . .
H6 H 0.1662 0.6309 0.3724 0.035 Uiso 1 1 calc R U . . .
C8 C -0.0689(3) 0.4948(2) 0.28378(19) 0.0266(7) Uani 1 1 d . . . . .
C9 C -0.0757(3) 0.4593(2) 0.2036(2) 0.0276(7) Uani 1 1 d . . . . .
C10 C -0.1070(3) 0.5028(2) 0.1313(2) 0.0347(8) Uani 1 1 d . . . . .
H9 H -0.1333 0.5548 0.1307 0.042 Uiso 1 1 calc R U . . .
C11 C -0.1001(3) 0.4704(3) 0.0600(2) 0.0426(10) Uani 1 1 d . . . . .
H8 H -0.1212 0.5004 0.0110 0.051 Uiso 1 1 calc R U . . .
C12 C -0.0625(3) 0.3949(3) 0.0606(2) 0.0465(11) Uani 1 1 d . . . . .
H2 H -0.0563 0.3731 0.0123 0.056 Uiso 1 1 calc R U . . .
C13 C 0.4744(3) 0.7196(2) 0.5415(2) 0.0371(9) Uani 1 1 d . . . . .
H3 H 0.5413 0.7049 0.5803 0.045 Uiso 1 1 calc R U . . .
C14 C 0.4442(3) 0.6925(2) 0.4618(2) 0.0313(8) Uani 1 1 d . . . . .
H16 H 0.4916 0.6603 0.4459 0.038 Uiso 1 1 calc R U . . .
C15 C -0.0405(3) 0.3825(2) 0.2026(2) 0.0328(8) Uani 1 1 d . . . . .
H10 H -0.0209 0.3517 0.2511 0.039 Uiso 1 1 calc R U . . .
C16 C -0.0338(3) 0.3508(2) 0.1320(2) 0.0400(9) Uani 1 1 d . . . . .
H7 H -0.0094 0.2983 0.1321 0.048 Uiso 1 1 calc R U . . .
C17 C -0.1358(3) 0.46435(19) 0.32894(19) 0.0251(7) Uani 1 1 d . . . . .
C18 C -0.1164(3) 0.4891(2) 0.4095(2) 0.0289(8) Uani 1 1 d . . . . .
H15 H -0.0619 0.5265 0.4341 0.035 Uiso 1 1 calc R U . . .
C19 C -0.1764(3) 0.4593(2) 0.4533(2) 0.0322(8) Uani 1 1 d . . . . .
H14 H -0.1630 0.4764 0.5079 0.039 Uiso 1 1 calc R U . . .
C20 C -0.2560(3) 0.4046(2) 0.4180(2) 0.0342(8) Uani 1 1 d . . . . .
H13 H -0.2970 0.3844 0.4483 0.041 Uiso 1 1 calc R U . . .
C21 C -0.2754(3) 0.3796(2) 0.3388(2) 0.0348(8) Uani 1 1 d . . . . .
H11 H -0.3291 0.3416 0.3148 0.042 Uiso 1 1 calc R U . . .
C22 C -0.2167(3) 0.4099(2) 0.2938(2) 0.0313(8) Uani 1 1 d . . . . .
H12 H -0.2318 0.3934 0.2388 0.038 Uiso 1 1 calc R U . . .
C23 C 0.9250(3) 0.7540(2) 0.5899(2) 0.0415(10) Uani 1 1 d . . . . .
H17 H 0.9447 0.7667 0.6463 0.050 Uiso 1 1 calc R U . . .
C24 C 0.8260(3) 0.7754(2) 0.5355(2) 0.0419(10) Uani 1 1 d . . . . .
H19 H 0.7773 0.8024 0.5548 0.050 Uiso 1 1 calc R U . . .
C25 C 0.7973(3) 0.7578(2) 0.4530(2) 0.0350(8) Uani 1 1 d . . . . .
H20 H 0.7292 0.7726 0.4158 0.042 Uiso 1 1 calc R U . . .
C26 C 0.8689(3) 0.7182(2) 0.4248(2) 0.0281(8) Uani 1 1 d . . . . .
C27 C 0.8437(3) 0.7024(2) 0.3352(2) 0.0290(8) Uani 1 1 d . . . . .
C28 C 0.7461(3) 0.6600(2) 0.29200(19) 0.0266(7) Uani 1 1 d . . . . .
C29 C 0.6838(3) 0.6218(2) 0.3263(2) 0.0261(7) Uani 1 1 d . . . . .
H30 H 0.6995 0.6280 0.3835 0.031 Uiso 1 1 calc R U . . .
C30 C 0.4635(3) 0.49617(19) 0.2807(2) 0.0269(7) Uani 1 1 d . . . . .
C31 C 0.3923(3) 0.4628(2) 0.3211(2) 0.0274(7) Uani 1 1 d . . . . .
C32 C 0.3102(3) 0.4115(2) 0.2792(2) 0.0385(9) Uani 1 1 d . . . . .
H29 H 0.2995 0.3973 0.2242 0.046 Uiso 1 1 calc R U . . .
C33 C 0.2438(3) 0.3812(2) 0.3179(2) 0.0439(10) Uani 1 1 d . . . . .
H26 H 0.1896 0.3448 0.2898 0.053 Uiso 1 1 calc R U . . .
C34 C 0.2559(3) 0.4034(2) 0.3965(2) 0.0394(9) Uani 1 1 d . . . . .
H18 H 0.2091 0.3836 0.4220 0.047 Uiso 1 1 calc R U . . .
C35 C 0.4459(3) 0.4769(2) 0.1938(2) 0.0260(7) Uani 1 1 d . . . . .
C36 C 0.4070(3) 0.5337(2) 0.1336(2) 0.0302(8) Uani 1 1 d . . . . .
H21 H 0.3909 0.5848 0.1480 0.036 Uiso 1 1 calc R U . . .
C37 C 0.3914(3) 0.5165(2) 0.0525(2) 0.0377(9) Uani 1 1 d . . . . .
H22 H 0.3639 0.5555 0.0115 0.045 Uiso 1 1 calc R U . . .
C38 C 0.4157(3) 0.4430(3) 0.0315(2) 0.0431(10) Uani 1 1 d . . . . .
H23 H 0.4053 0.4312 -0.0240 0.052 Uiso 1 1 calc R U . . .
C39 C 0.4552(3) 0.3861(2) 0.0912(2) 0.0421(10) Uani 1 1 d . . . . .
H24 H 0.4729 0.3355 0.0765 0.050 Uiso 1 1 calc R U . . .
C40 C 0.4692(3) 0.4023(2) 0.1720(2) 0.0359(9) Uani 1 1 d . . . . .
H25 H 0.4947 0.3626 0.2125 0.043 Uiso 1 1 calc R U . . .
C41 C 0.3366(3) 0.4547(2) 0.4379(2) 0.0352(9) Uani 1 1 d . . . . .
H27 H 0.3453 0.4701 0.4923 0.042 Uiso 1 1 calc R U . . .
C42 C 0.4047(3) 0.4839(2) 0.4011(2) 0.0293(8) Uani 1 1 d . . . . .
H28 H 0.4606 0.5185 0.4306 0.035 Uiso 1 1 calc R U . . .
C43 C 0.9677(3) 0.6967(2) 0.4797(2) 0.0325(8) Uani 1 1 d . . . . .
H31 H 1.0168 0.6699 0.4608 0.039 Uiso 1 1 calc R U . . .
C44 C 0.9951(3) 0.7143(2) 0.5618(2) 0.0411(10) Uani 1 1 d . . . . .
H32 H 1.0627 0.6988 0.5992 0.049 Uiso 1 1 calc R U . . .
H1N H 0.057(3) 0.559(3) 0.232(3) 0.062 Uiso 1 1 d . U . . .
H3N H 0.589(3) 0.565(3) 0.235(3) 0.062 Uiso 1 1 d . 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
Br2 C6 1.898(3) . ?
Br1 C28 1.894(3) . ?
O1 C5 1.228(4) . ?
O2 C27 1.219(4) . ?
N1 C7 1.344(4) . ?
N1 N2 1.370(4) . ?
N1 H1N 0.83(4) . ?
N2 C8 1.292(4) . ?
N3 C29 1.341(4) . ?
N3 N4 1.380(4) . ?
N3 H3N 0.84(4) . ?
N4 C30 1.298(4) . ?
C1 C2 1.384(5) . ?
C1 C13 1.389(5) . ?
C1 H1 0.9500 . ?
C2 C3 1.392(5) . ?
C2 H5 0.9500 . ?
C3 C4 1.394(5) . ?
C3 H4 0.9500 . ?
C4 C14 1.387(5) . ?
C4 C5 1.508(5) . ?
C5 C6 1.443(5) . ?
C6 C7 1.350(4) . ?
C7 H6 0.9500 . ?
C8 C17 1.480(4) . ?
C8 C9 1.497(4) . ?
C9 C15 1.390(5) . ?
C9 C10 1.394(5) . ?
C10 C11 1.392(5) . ?
C10 H9 0.9500 . ?
C11 C12 1.378(6) . ?
C11 H8 0.9500 . ?
C12 C16 1.387(6) . ?
C12 H2 0.9500 . ?
C13 C14 1.383(5) . ?
C13 H3 0.9500 . ?
C14 H16 0.9500 . ?
C15 C16 1.376(5) . ?
C15 H10 0.9500 . ?
C16 H7 0.9500 . ?
C17 C22 1.395(5) . ?
C17 C18 1.400(4) . ?
C18 C19 1.386(5) . ?
C18 H15 0.9500 . ?
C19 C20 1.386(5) . ?
C19 H14 0.9500 . ?
C20 C21 1.381(5) . ?
C20 H13 0.9500 . ?
C21 C22 1.389(5) . ?
C21 H11 0.9500 . ?
C22 H12 0.9500 . ?
C23 C44 1.379(5) . ?
C23 C24 1.384(6) . ?
C23 H17 0.9500 . ?
C24 C25 1.386(5) . ?
C24 H19 0.9500 . ?
C25 C26 1.396(5) . ?
C25 H20 0.9500 . ?
C26 C43 1.385(5) . ?
C26 C27 1.504(5) . ?
C27 C28 1.453(5) . ?
C28 C29 1.351(4) . ?
C29 H30 0.9500 . ?
C30 C31 1.484(4) . ?
C30 C35 1.486(4) . ?
C31 C42 1.393(4) . ?
C31 C32 1.395(5) . ?
C32 C33 1.391(5) . ?
C32 H29 0.9500 . ?
C33 C34 1.375(5) . ?
C33 H26 0.9500 . ?
C34 C41 1.381(5) . ?
C34 H18 0.9500 . ?
C35 C36 1.387(5) . ?
C35 C40 1.392(5) . ?
C36 C37 1.387(5) . ?
C36 H21 0.9500 . ?
C37 C38 1.373(5) . ?
C37 H22 0.9500 . ?
C38 C39 1.383(6) . ?
C38 H23 0.9500 . ?
C39 C40 1.384(5) . ?
C39 H24 0.9500 . ?
C40 H25 0.9500 . ?
C41 C42 1.379(5) . ?
C41 H27 0.9500 . ?
C42 H28 0.9500 . ?
C43 C44 1.381(5) . ?
C43 H31 0.9500 . ?
C44 H32 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7 N1 N2 120.7(3) . . ?
C7 N1 H1N 116(3) . . ?
N2 N1 H1N 123(3) . . ?
C8 N2 N1 116.3(3) . . ?
C29 N3 N4 120.2(3) . . ?
C29 N3 H3N 120(3) . . ?
N4 N3 H3N 120(3) . . ?
C30 N4 N3 115.8(3) . . ?
C2 C1 C13 119.6(4) . . ?
C2 C1 H1 120.2 . . ?
C13 C1 H1 120.2 . . ?
C1 C2 C3 120.5(4) . . ?
C1 C2 H5 119.8 . . ?
C3 C2 H5 119.8 . . ?
C2 C3 C4 119.8(4) . . ?
C2 C3 H4 120.1 . . ?
C4 C3 H4 120.1 . . ?
C14 C4 C3 119.3(3) . . ?
C14 C4 C5 118.9(3) . . ?
C3 C4 C5 121.6(3) . . ?
O1 C5 C6 122.6(3) . . ?
O1 C5 C4 119.1(3) . . ?
C6 C5 C4 118.3(3) . . ?
C7 C6 C5 126.7(3) . . ?
C7 C6 Br2 116.9(3) . . ?
C5 C6 Br2 115.8(2) . . ?
N1 C7 C6 123.7(3) . . ?
N1 C7 H6 118.1 . . ?
C6 C7 H6 118.1 . . ?
N2 C8 C17 116.9(3) . . ?
N2 C8 C9 122.4(3) . . ?
C17 C8 C9 120.4(3) . . ?
C15 C9 C10 118.9(3) . . ?
C15 C9 C8 118.7(3) . . ?
C10 C9 C8 122.1(3) . . ?
C11 C10 C9 120.3(4) . . ?
C11 C10 H9 119.9 . . ?
C9 C10 H9 119.9 . . ?
C12 C11 C10 120.0(4) . . ?
C12 C11 H8 120.0 . . ?
C10 C11 H8 120.0 . . ?
C11 C12 C16 119.8(4) . . ?
C11 C12 H2 120.1 . . ?
C16 C12 H2 120.1 . . ?
C14 C13 C1 120.1(4) . . ?
C14 C13 H3 119.9 . . ?
C1 C13 H3 119.9 . . ?
C13 C14 C4 120.6(3) . . ?
C13 C14 H16 119.7 . . ?
C4 C14 H16 119.7 . . ?
C16 C15 C9 120.5(4) . . ?
C16 C15 H10 119.7 . . ?
C9 C15 H10 119.7 . . ?
C15 C16 C12 120.4(4) . . ?
C15 C16 H7 119.8 . . ?
C12 C16 H7 119.8 . . ?
C22 C17 C18 118.9(3) . . ?
C22 C17 C8 121.5(3) . . ?
C18 C17 C8 119.6(3) . . ?
C19 C18 C17 120.2(3) . . ?
C19 C18 H15 119.9 . . ?
C17 C18 H15 119.9 . . ?
C20 C19 C18 120.4(3) . . ?
C20 C19 H14 119.8 . . ?
C18 C19 H14 119.8 . . ?
C21 C20 C19 119.7(3) . . ?
C21 C20 H13 120.1 . . ?
C19 C20 H13 120.1 . . ?
C20 C21 C22 120.4(3) . . ?
C20 C21 H11 119.8 . . ?
C22 C21 H11 119.8 . . ?
C21 C22 C17 120.3(3) . . ?
C21 C22 H12 119.8 . . ?
C17 C22 H12 119.8 . . ?
C44 C23 C24 119.7(4) . . ?
C44 C23 H17 120.2 . . ?
C24 C23 H17 120.2 . . ?
C23 C24 C25 120.4(4) . . ?
C23 C24 H19 119.8 . . ?
C25 C24 H19 119.8 . . ?
C24 C25 C26 119.7(4) . . ?
C24 C25 H20 120.2 . . ?
C26 C25 H20 120.2 . . ?
C43 C26 C25 119.6(3) . . ?
C43 C26 C27 118.9(3) . . ?
C25 C26 C27 121.4(3) . . ?
O2 C27 C28 122.9(3) . . ?
O2 C27 C26 119.7(3) . . ?
C28 C27 C26 117.4(3) . . ?
C29 C28 C27 126.4(3) . . ?
C29 C28 Br1 117.8(3) . . ?
C27 C28 Br1 115.4(2) . . ?
N3 C29 C28 124.4(3) . . ?
N3 C29 H30 117.8 . . ?
C28 C29 H30 117.8 . . ?
N4 C30 C31 116.6(3) . . ?
N4 C30 C35 123.3(3) . . ?
C31 C30 C35 120.1(3) . . ?
C42 C31 C32 118.7(3) . . ?
C42 C31 C30 120.5(3) . . ?
C32 C31 C30 120.8(3) . . ?
C33 C32 C31 120.0(3) . . ?
C33 C32 H29 120.0 . . ?
C31 C32 H29 120.0 . . ?
C34 C33 C32 120.6(4) . . ?
C34 C33 H26 119.7 . . ?
C32 C33 H26 119.7 . . ?
C33 C34 C41 119.5(3) . . ?
C33 C34 H18 120.2 . . ?
C41 C34 H18 120.2 . . ?
C36 C35 C40 119.3(3) . . ?
C36 C35 C30 120.2(3) . . ?
C40 C35 C30 120.5(3) . . ?
C37 C36 C35 120.5(3) . . ?
C37 C36 H21 119.7 . . ?
C35 C36 H21 119.7 . . ?
C38 C37 C36 119.9(4) . . ?
C38 C37 H22 120.0 . . ?
C36 C37 H22 120.0 . . ?
C37 C38 C39 120.1(3) . . ?
C37 C38 H23 120.0 . . ?
C39 C38 H23 120.0 . . ?
C40 C39 C38 120.4(4) . . ?
C40 C39 H24 119.8 . . ?
C38 C39 H24 119.8 . . ?
C39 C40 C35 119.8(4) . . ?
C39 C40 H25 120.1 . . ?
C35 C40 H25 120.1 . . ?
C42 C41 C34 120.6(3) . . ?
C42 C41 H27 119.7 . . ?
C34 C41 H27 119.7 . . ?
C41 C42 C31 120.5(3) . . ?
C41 C42 H28 119.7 . . ?
C31 C42 H28 119.7 . . ?
C44 C43 C26 120.2(3) . . ?
C44 C43 H31 119.9 . . ?
C26 C43 H31 119.9 . . ?
C23 C44 C43 120.5(4) . . ?
C23 C44 H32 119.7 . . ?
C43 C44 H32 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
C7 N1 N2 C8 -169.5(3) . . . . ?
C29 N3 N4 C30 -176.7(3) . . . . ?
C13 C1 C2 C3 2.1(6) . . . . ?
C1 C2 C3 C4 -2.3(6) . . . . ?
C2 C3 C4 C14 0.5(5) . . . . ?
C2 C3 C4 C5 -175.3(3) . . . . ?
C14 C4 C5 O1 -47.8(5) . . . . ?
C3 C4 C5 O1 128.0(4) . . . . ?
C14 C4 C5 C6 130.8(3) . . . . ?
C3 C4 C5 C6 -53.4(5) . . . . ?
O1 C5 C6 C7 164.9(4) . . . . ?
C4 C5 C6 C7 -13.6(5) . . . . ?
O1 C5 C6 Br2 -6.5(5) . . . . ?
C4 C5 C6 Br2 175.0(2) . . . . ?
N2 N1 C7 C6 -179.6(3) . . . . ?
C5 C6 C7 N1 -170.2(4) . . . . ?
Br2 C6 C7 N1 1.1(5) . . . . ?
N1 N2 C8 C17 177.9(3) . . . . ?
N1 N2 C8 C9 4.5(5) . . . . ?
N2 C8 C9 C15 106.1(4) . . . . ?
C17 C8 C9 C15 -67.2(4) . . . . ?
N2 C8 C9 C10 -68.0(5) . . . . ?
C17 C8 C9 C10 118.7(4) . . . . ?
C15 C9 C10 C11 -1.9(5) . . . . ?
C8 C9 C10 C11 172.2(3) . . . . ?
C9 C10 C11 C12 0.3(6) . . . . ?
C10 C11 C12 C16 1.3(6) . . . . ?
C2 C1 C13 C14 -0.1(6) . . . . ?
C1 C13 C14 C4 -1.7(5) . . . . ?
C3 C4 C14 C13 1.5(5) . . . . ?
C5 C4 C14 C13 177.3(3) . . . . ?
C10 C9 C15 C16 1.8(5) . . . . ?
C8 C9 C15 C16 -172.4(3) . . . . ?
C9 C15 C16 C12 -0.2(6) . . . . ?
C11 C12 C16 C15 -1.4(6) . . . . ?
N2 C8 C17 C22 177.5(3) . . . . ?
C9 C8 C17 C22 -8.9(5) . . . . ?
N2 C8 C17 C18 -4.0(5) . . . . ?
C9 C8 C17 C18 169.6(3) . . . . ?
C22 C17 C18 C19 0.5(5) . . . . ?
C8 C17 C18 C19 -178.1(3) . . . . ?
C17 C18 C19 C20 0.1(5) . . . . ?
C18 C19 C20 C21 0.1(6) . . . . ?
C19 C20 C21 C22 -1.0(6) . . . . ?
C20 C21 C22 C17 1.6(6) . . . . ?
C18 C17 C22 C21 -1.3(5) . . . . ?
C8 C17 C22 C21 177.2(3) . . . . ?
C44 C23 C24 C25 -0.6(6) . . . . ?
C23 C24 C25 C26 0.0(6) . . . . ?
C24 C25 C26 C43 0.2(5) . . . . ?
C24 C25 C26 C27 -176.1(3) . . . . ?
C43 C26 C27 O2 -51.8(5) . . . . ?
C25 C26 C27 O2 124.5(4) . . . . ?
C43 C26 C27 C28 127.7(4) . . . . ?
C25 C26 C27 C28 -55.9(4) . . . . ?
O2 C27 C28 C29 167.8(4) . . . . ?
C26 C27 C28 C29 -11.7(5) . . . . ?
O2 C27 C28 Br1 -5.3(5) . . . . ?
C26 C27 C28 Br1 175.2(2) . . . . ?
N4 N3 C29 C28 -176.1(3) . . . . ?
C27 C28 C29 N3 -171.8(3) . . . . ?
Br1 C28 C29 N3 1.1(5) . . . . ?
N3 N4 C30 C31 -177.7(3) . . . . ?
N3 N4 C30 C35 0.8(5) . . . . ?
N4 C30 C31 C42 2.0(5) . . . . ?
C35 C30 C31 C42 -176.6(3) . . . . ?
N4 C30 C31 C32 -179.6(3) . . . . ?
C35 C30 C31 C32 1.8(5) . . . . ?
C42 C31 C32 C33 -1.2(6) . . . . ?
C30 C31 C32 C33 -179.6(4) . . . . ?
C31 C32 C33 C34 2.3(6) . . . . ?
C32 C33 C34 C41 -1.7(6) . . . . ?
N4 C30 C35 C36 -69.8(5) . . . . ?
C31 C30 C35 C36 108.7(4) . . . . ?
N4 C30 C35 C40 109.5(4) . . . . ?
C31 C30 C35 C40 -72.0(4) . . . . ?
C40 C35 C36 C37 0.0(5) . . . . ?
C30 C35 C36 C37 179.3(3) . . . . ?
C35 C36 C37 C38 -0.7(5) . . . . ?
C36 C37 C38 C39 0.3(6) . . . . ?
C37 C38 C39 C40 0.9(6) . . . . ?
C38 C39 C40 C35 -1.6(6) . . . . ?
C36 C35 C40 C39 1.2(5) . . . . ?
C30 C35 C40 C39 -178.1(3) . . . . ?
C33 C34 C41 C42 0.1(6) . . . . ?
C34 C41 C42 C31 0.9(6) . . . . ?
C32 C31 C42 C41 -0.3(5) . . . . ?
C30 C31 C42 C41 178.1(3) . . . . ?
C25 C26 C43 C44 0.2(5) . . . . ?
C27 C26 C43 C44 176.5(3) . . . . ?
C24 C23 C44 C43 1.0(6) . . . . ?
C26 C43 C44 C23 -0.8(6) . . . . ?

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
N3 H3N Br1 0.84(4) 2.64(4) 3.047(3) 111(4) .
N1 H1N Br2 0.83(4) 2.55(4) 3.011(3) 116(4) .
N3 H3N Br1 0.84(4) 2.64(4) 3.047(3) 111(4) .
N1 H1N Br2 0.83(4) 2.55(4) 3.011(3) 116(4) .

_refine_diff_density_max         0.568
_refine_diff_density_min         -0.594
_refine_diff_density_rms         0.091

####################################################################### 
# 
# 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_hs
_database_code_depnum_ccdc_archive 'CCDC 2190575'
loop_
_audit_author_name
_audit_author_address
'kun he'
;yunnan university
China
;
_audit_update_record             
;
2022-07-15 deposited with the CCDC.	2024-11-14 downloaded from the CCDC.
;
_audit_creation_date             2021-12-16
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.09.19 svn.r3010 for OlexSys, GUI svn.r4874)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C24 H22 N2 O'
_chemical_formula_sum            'C24 H22 N2 O'
_chemical_formula_weight         354.43
_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           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   14.550(19)
_cell_length_b                   6.415(9)
_cell_length_c                   21.40(3)
_cell_angle_alpha                90
_cell_angle_beta                 100.555(11)
_cell_angle_gamma                90
_cell_volume                     1964(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    602
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      16.89
_cell_measurement_theta_min      2.85
_shelx_estimated_absorpt_T_max   0.996
_shelx_estimated_absorpt_T_min   0.987
_exptl_absorpt_coefficient_mu    0.074
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.199
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.06
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1497
_diffrn_reflns_av_unetI/netI     0.1862
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            14294
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.250
_diffrn_reflns_theta_min         1.862
_diffrn_ambient_temperature      296(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1281
_reflns_number_total             3558
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.183
_refine_diff_density_min         -0.238
_refine_diff_density_rms         0.055
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     250
_refine_ls_number_reflns         3558
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2217
_refine_ls_R_factor_gt           0.0824
_refine_ls_restrained_S_all      1.014
_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)+(0.0400P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1761
_refine_ls_wR_factor_ref         0.2388
_refine_special_details          ?
_olex2_refinement_description    
;
1. Others
 Fixed Uiso: H1(0.099) H2(0.116) H3(0.12) H4(0.116) H5(0.099) H8(0.085)
 H9(0.089) H12(0.079) H13(0.092) H14(0.098) H15(0.094) H16(0.082) H18(0.085)
 H21(0.093) H22(0.083) H23A(0.163) H23B(0.163) H23C(0.163) H24A(0.145)
 H24B(0.145) H24C(0.145)
 Fixed X: H1(0.325949) H2(0.270416) H3(0.112509) H4(0.010048) H5(0.063167)
 H8(0.364449) H9(0.422017) H12(0.236005) H13(0.086306) H14(-0.028659)
 H15(0.004742) H16(0.153207) H18(0.285716) H21(0.506962) H22(0.439166)
 H23A(0.398334) H23B(0.313861) H23C(0.301664) H24A(0.530786) H24B(0.437295)
 H24C(0.513453)
 Fixed Y: H1(1.208115) H2(1.489413) H3(1.537809) H4(1.309826) H5(1.035367)
 H8(0.893183) H9(0.628082) H12(0.649167) H13(0.720954) H14(0.470461)
 H15(0.150887) H16(0.072852) H18(0.127131) H21(-0.239326) H22(0.047012) H23A(-
 0.192765) H23B(-0.316497) H23C(-0.081984) H24A(-0.476618) H24B(-0.529431)
 H24C(-0.392423)
 Fixed Z: H1(-0.147684) H2(-0.211414) H3(-0.24337) H4(-0.211583) H5(-0.144936)
 H8(-0.11942) H9(-0.056043) H12(0.092148) H13(0.108394) H14(0.086353)
 H15(0.048056) H16(0.03347) H18(0.161349) H21(0.080396) H22(0.026838)
 H23A(0.273363) H23B(0.23451) H23C(0.251912) H24A(0.163753) H24B(0.186906)
 H24C(0.229382)
;
_atom_sites_solution_hydrogens   mixed
_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 0.1777(2) 0.8243(5) -0.06776(17) 0.0815(10) Uani 1 1 d . . . . .
N1 N 0.3115(3) 0.5573(6) -0.0209(2) 0.0707(12) Uani 1 1 d . . . . .
N2 N 0.3554(3) 0.3959(6) 0.0157(2) 0.0684(11) Uani 1 1 d . . . . .
C1 C 0.2618(4) 1.2278(8) -0.1599(3) 0.0821(16) Uani 1 1 d . . . . .
H1 H 0.325949 1.208115 -0.147684 0.099 Uiso 1 1 calc R U . . .
C2 C 0.2285(5) 1.3965(8) -0.1985(3) 0.0968(18) Uani 1 1 d . . . . .
H2 H 0.270416 1.489413 -0.211414 0.116 Uiso 1 1 calc R U . . .
C3 C 0.1347(6) 1.4257(9) -0.2174(3) 0.0998(19) Uani 1 1 d . . . . .
H3 H 0.112509 1.537809 -0.243370 0.120 Uiso 1 1 calc R U . . .
C4 C 0.0740(5) 1.2907(10) -0.1982(3) 0.0966(19) Uani 1 1 d . . . . .
H4 H 0.010048 1.309826 -0.211583 0.116 Uiso 1 1 calc R U . . .
C5 C 0.1059(4) 1.1242(8) -0.1587(3) 0.0827(16) Uani 1 1 d . . . . .
H5 H 0.063167 1.035367 -0.144936 0.099 Uiso 1 1 calc R U . . .
C6 C 0.2006(3) 1.0890(7) -0.1395(2) 0.0644(13) Uani 1 1 d . . . . .
C7 C 0.2334(3) 0.9046(7) -0.0987(2) 0.0636(13) Uani 1 1 d . . . . .
C8 C 0.3258(3) 0.8291(7) -0.0950(2) 0.0708(14) Uani 1 1 d . . . . .
H8 H 0.364449 0.893183 -0.119420 0.085 Uiso 1 1 calc R U . . .
C9 C 0.3601(4) 0.6663(8) -0.0570(3) 0.0744(14) Uani 1 1 d . . . . .
H9 H 0.422017 0.628082 -0.056043 0.089 Uiso 1 1 calc R U . . .
C10 C 0.3075(3) 0.3003(7) 0.0525(2) 0.0616(13) Uani 1 1 d . . . . .
C11 C 0.2108(3) 0.3549(7) 0.0604(2) 0.0597(12) Uani 1 1 d . . . . .
C12 C 0.1897(3) 0.5480(7) 0.0833(2) 0.0657(13) Uani 1 1 d . . . . .
H12 H 0.236005 0.649167 0.092148 0.079 Uiso 1 1 calc R U . . .
C13 C 0.1001(4) 0.5912(8) 0.0930(2) 0.0771(15) Uani 1 1 d . . . . .
H13 H 0.086306 0.720954 0.108394 0.092 Uiso 1 1 calc R U . . .
C14 C 0.0315(3) 0.4417(9) 0.0799(2) 0.0816(16) Uani 1 1 d . . . . .
H14 H -0.028659 0.470461 0.086353 0.098 Uiso 1 1 calc R U . . .
C15 C 0.0517(4) 0.2505(9) 0.0572(2) 0.0780(15) Uani 1 1 d . . . . .
H15 H 0.004742 0.150887 0.048056 0.094 Uiso 1 1 calc R U . . .
C16 C 0.1401(3) 0.2043(7) 0.0480(2) 0.0679(14) Uani 1 1 d . . . . .
H16 H 0.153207 0.072852 0.033470 0.082 Uiso 1 1 calc R U . . .
C17 C 0.3542(3) 0.1194(7) 0.0877(2) 0.0583(12) Uani 1 1 d . . . . .
C18 C 0.3312(3) 0.0538(7) 0.1451(3) 0.0710(14) Uani 1 1 d . . . . .
H18 H 0.285716 0.127131 0.161349 0.085 Uiso 1 1 calc R U . . .
C19 C 0.3735(4) -0.1173(8) 0.1790(2) 0.0722(14) Uani 1 1 d . . . . .
C20 C 0.4401(4) -0.2306(7) 0.1542(3) 0.0707(15) Uani 1 1 d . . . . .
C21 C 0.4625(3) -0.1649(8) 0.0973(3) 0.0772(15) Uani 1 1 d . . . . .
H21 H 0.506962 -0.239326 0.080396 0.093 Uiso 1 1 calc R U . . .
C22 C 0.4213(3) 0.0070(7) 0.0647(2) 0.0695(14) Uani 1 1 d . . . . .
H22 H 0.439166 0.047012 0.026838 0.083 Uiso 1 1 calc R U . . .
C23 C 0.3442(4) -0.1831(9) 0.2403(3) 0.109(2) Uani 1 1 d . . . . .
H23A H 0.398334 -0.192765 0.273363 0.163 Uiso 1 1 calc R U . . .
H23B H 0.313861 -0.316497 0.234510 0.163 Uiso 1 1 calc R U . . .
H23C H 0.301664 -0.081984 0.251912 0.163 Uiso 1 1 calc R U . . .
C24 C 0.4845(4) -0.4250(7) 0.1865(3) 0.0965(19) Uani 1 1 d . . . . .
H24A H 0.530786 -0.476618 0.163753 0.145 Uiso 1 1 calc R U . . .
H24B H 0.437295 -0.529431 0.186906 0.145 Uiso 1 1 calc R U . . .
H24C H 0.513453 -0.392423 0.229382 0.145 Uiso 1 1 calc R U . . .
H1D H 0.250(4) 0.589(8) -0.026(3) 0.11(2) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C7 1.248(5) . ?
N1 N2 1.382(5) . ?
N1 C9 1.337(6) . ?
N1 H1D 0.90(5) . ?
N2 C10 1.296(5) . ?
C1 H1 0.9300 . ?
C1 C2 1.393(7) . ?
C1 C6 1.385(6) . ?
C2 H2 0.9300 . ?
C2 C3 1.364(8) . ?
C3 H3 0.9300 . ?
C3 C4 1.353(8) . ?
C4 H4 0.9300 . ?
C4 C5 1.389(7) . ?
C5 H5 0.9300 . ?
C5 C6 1.382(6) . ?
C6 C7 1.496(6) . ?
C7 C8 1.418(6) . ?
C8 H8 0.9300 . ?
C8 C9 1.361(6) . ?
C9 H9 0.9300 . ?
C10 C11 1.489(6) . ?
C10 C17 1.480(6) . ?
C11 C12 1.387(6) . ?
C11 C16 1.401(6) . ?
C12 H12 0.9300 . ?
C12 C13 1.386(6) . ?
C13 H13 0.9300 . ?
C13 C14 1.375(6) . ?
C14 H14 0.9300 . ?
C14 C15 1.370(6) . ?
C15 H15 0.9300 . ?
C15 C16 1.370(6) . ?
C16 H16 0.9300 . ?
C17 C18 1.394(6) . ?
C17 C22 1.377(6) . ?
C18 H18 0.9300 . ?
C18 C19 1.395(6) . ?
C19 C20 1.392(7) . ?
C19 C23 1.512(7) . ?
C20 C21 1.382(7) . ?
C20 C24 1.512(6) . ?
C21 H21 0.9300 . ?
C21 C22 1.382(6) . ?
C22 H22 0.9300 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 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
N2 N1 H1D 126(4) . . ?
C9 N1 N2 118.7(5) . . ?
C9 N1 H1D 115(4) . . ?
C10 N2 N1 117.0(4) . . ?
C2 C1 H1 119.6 . . ?
C6 C1 H1 119.6 . . ?
C6 C1 C2 120.8(5) . . ?
C1 C2 H2 119.9 . . ?
C3 C2 C1 120.2(6) . . ?
C3 C2 H2 119.9 . . ?
C2 C3 H3 120.1 . . ?
C4 C3 C2 119.7(6) . . ?
C4 C3 H3 120.1 . . ?
C3 C4 H4 119.6 . . ?
C3 C4 C5 120.9(6) . . ?
C5 C4 H4 119.6 . . ?
C4 C5 H5 119.7 . . ?
C6 C5 C4 120.7(5) . . ?
C6 C5 H5 119.7 . . ?
C1 C6 C7 122.5(4) . . ?
C5 C6 C1 117.7(5) . . ?
C5 C6 C7 119.7(5) . . ?
O1 C7 C6 117.9(4) . . ?
O1 C7 C8 122.1(5) . . ?
C8 C7 C6 120.0(5) . . ?
C7 C8 H8 118.8 . . ?
C9 C8 C7 122.4(5) . . ?
C9 C8 H8 118.8 . . ?
N1 C9 C8 124.9(5) . . ?
N1 C9 H9 117.6 . . ?
C8 C9 H9 117.6 . . ?
N2 C10 C11 125.6(4) . . ?
N2 C10 C17 115.7(4) . . ?
C17 C10 C11 118.7(4) . . ?
C12 C11 C10 121.7(4) . . ?
C12 C11 C16 118.7(4) . . ?
C16 C11 C10 119.5(4) . . ?
C11 C12 H12 119.7 . . ?
C13 C12 C11 120.5(4) . . ?
C13 C12 H12 119.7 . . ?
C12 C13 H13 120.1 . . ?
C14 C13 C12 119.8(5) . . ?
C14 C13 H13 120.1 . . ?
C13 C14 H14 119.9 . . ?
C15 C14 C13 120.2(5) . . ?
C15 C14 H14 119.9 . . ?
C14 C15 H15 119.6 . . ?
C16 C15 C14 120.9(5) . . ?
C16 C15 H15 119.6 . . ?
C11 C16 H16 120.0 . . ?
C15 C16 C11 120.0(5) . . ?
C15 C16 H16 120.0 . . ?
C18 C17 C10 121.6(5) . . ?
C22 C17 C10 121.1(5) . . ?
C22 C17 C18 117.3(4) . . ?
C17 C18 H18 118.6 . . ?
C17 C18 C19 122.8(5) . . ?
C19 C18 H18 118.6 . . ?
C18 C19 C23 120.3(5) . . ?
C20 C19 C18 118.9(5) . . ?
C20 C19 C23 120.8(5) . . ?
C19 C20 C24 121.7(5) . . ?
C21 C20 C19 118.0(5) . . ?
C21 C20 C24 120.3(5) . . ?
C20 C21 H21 118.7 . . ?
C22 C21 C20 122.6(5) . . ?
C22 C21 H21 118.7 . . ?
C17 C22 C21 120.4(5) . . ?
C17 C22 H22 119.8 . . ?
C21 C22 H22 119.8 . . ?
C19 C23 H23A 109.5 . . ?
C19 C23 H23B 109.5 . . ?
C19 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C20 C24 H24A 109.5 . . ?
C20 C24 H24B 109.5 . . ?
C20 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 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 C7 C8 C9 -0.8(7) . . . . ?
N1 N2 C10 C11 -2.5(7) . . . . ?
N1 N2 C10 C17 176.0(4) . . . . ?
N2 N1 C9 C8 -179.7(4) . . . . ?
N2 C10 C11 C12 -61.0(6) . . . . ?
N2 C10 C11 C16 122.7(5) . . . . ?
N2 C10 C17 C18 154.3(4) . . . . ?
N2 C10 C17 C22 -26.6(6) . . . . ?
C1 C2 C3 C4 0.4(9) . . . . ?
C1 C6 C7 O1 159.6(5) . . . . ?
C1 C6 C7 C8 -19.1(7) . . . . ?
C2 C1 C6 C5 -0.2(8) . . . . ?
C2 C1 C6 C7 179.3(5) . . . . ?
C2 C3 C4 C5 0.9(9) . . . . ?
C3 C4 C5 C6 -1.9(9) . . . . ?
C4 C5 C6 C1 1.5(8) . . . . ?
C4 C5 C6 C7 -178.0(5) . . . . ?
C5 C6 C7 O1 -21.0(7) . . . . ?
C5 C6 C7 C8 160.4(5) . . . . ?
C6 C1 C2 C3 -0.8(9) . . . . ?
C6 C7 C8 C9 177.8(4) . . . . ?
C7 C8 C9 N1 1.9(8) . . . . ?
C9 N1 N2 C10 176.7(4) . . . . ?
C10 C11 C12 C13 -176.9(4) . . . . ?
C10 C11 C16 C15 177.7(4) . . . . ?
C10 C17 C18 C19 179.5(4) . . . . ?
C10 C17 C22 C21 -178.3(4) . . . . ?
C11 C10 C17 C18 -27.1(6) . . . . ?
C11 C10 C17 C22 152.0(4) . . . . ?
C11 C12 C13 C14 0.0(7) . . . . ?
C12 C11 C16 C15 1.4(7) . . . . ?
C12 C13 C14 C15 0.0(8) . . . . ?
C13 C14 C15 C16 0.7(8) . . . . ?
C14 C15 C16 C11 -1.4(7) . . . . ?
C16 C11 C12 C13 -0.7(7) . . . . ?
C17 C10 C11 C12 120.5(5) . . . . ?
C17 C10 C11 C16 -55.8(6) . . . . ?
C17 C18 C19 C20 -1.4(7) . . . . ?
C17 C18 C19 C23 -178.8(4) . . . . ?
C18 C17 C22 C21 0.8(6) . . . . ?
C18 C19 C20 C21 1.3(7) . . . . ?
C18 C19 C20 C24 -176.3(4) . . . . ?
C19 C20 C21 C22 -0.2(7) . . . . ?
C20 C21 C22 C17 -1.0(7) . . . . ?
C22 C17 C18 C19 0.3(7) . . . . ?
C23 C19 C20 C21 178.7(5) . . . . ?
C23 C19 C20 C24 1.0(7) . . . . ?
C24 C20 C21 C22 177.5(4) . . . . ?

_shelx_SHELXL_version_number     2016/6
_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_YY
_database_code_depnum_ccdc_archive 'CCDC 2190573'
loop_
_audit_author_name
_audit_author_address
'kun he'
;yunnan university
China
;
_audit_update_record             
;
2022-07-15 deposited with the CCDC.	2024-11-14 downloaded from the CCDC.
;
_audit_creation_date             2021-12-16
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.09.19 svn.r3010 for OlexSys, GUI svn.r4874)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H14 N2 O'
_chemical_formula_sum            'C16 H14 N2 O'
_chemical_formula_weight         250.29
_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      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'
'-x, -y, -z'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'
'x-1/2, y, -z-1/2'

_cell_length_a                   11.568(3)
_cell_length_b                   7.6379(19)
_cell_length_c                   30.481(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2693.3(11)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    2020
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      21.20
_cell_measurement_theta_min      2.21
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.235
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1056
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.16
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0454
_diffrn_reflns_av_unetI/netI     0.0390
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       39
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            15473
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.498
_diffrn_reflns_theta_min         1.336
_diffrn_ambient_temperature      296(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_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_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1885
_reflns_number_total             3069
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.212
_refine_diff_density_min         -0.192
_refine_diff_density_rms         0.035
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     176
_refine_ls_number_reflns         3069
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0911
_refine_ls_R_factor_gt           0.0548
_refine_ls_restrained_S_all      1.043
_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)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1584
_refine_ls_wR_factor_ref         0.1834
_refine_special_details          ?
_olex2_refinement_description    
;
1. Others
 Fixed Uiso: H1(0.077) H2(0.082) H3(0.082) H4(0.083) H5(0.073) H7(0.073)
 H8(0.073) H9(0.067) H12(0.069) H13(0.081) H14(0.082) H15(0.081) H16(0.068)
 Fixed X: H1(0.460441) H2(0.47295) H3(0.616813) H4(0.751396) H5(0.741792)
 H7(0.532487) H8(0.767917) H9(0.756744) H12(0.741944) H13(0.726713)
 H14(0.593925) H15(0.47425) H16(0.486607)
 Fixed Y: H1(0.529382) H2(0.433259) H3(0.245857) H4(0.153518) H5(0.246205)
 H7(0.539227) H8(0.34213) H9(0.429292) H12(0.485979) H13(0.560105)
 H14(0.765065) H15(0.895451) H16(0.819186)
 Fixed Z: H1(0.220005) H2(0.147966) H3(0.127167) H4(0.177526) H5(0.249324)
 H7(0.295282) H8(0.383772) H9(0.453202) H12(0.518816) H13(0.591888)
 H14(0.614053) H15(0.563422) H16(0.490306)
;
_atom_sites_solution_hydrogens   mixed
_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 0.55786(12) 0.67828(18) 0.42281(4) 0.0646(4) Uani 1 1 d . . . . .
N1 N 0.65926(15) 0.4081(2) 0.31705(5) 0.0603(5) Uani 1 1 d . . . . .
N2 N 0.64301(15) 0.4772(2) 0.35867(5) 0.0605(5) Uani 1 1 d . . . . .
C1 C 0.51945(18) 0.4535(3) 0.21175(6) 0.0639(6) Uani 1 1 d . . . . .
H1 H 0.460441 0.529382 0.220005 0.077 Uiso 1 1 calc R U . . .
C2 C 0.52698(19) 0.3955(3) 0.16849(6) 0.0679(6) Uani 1 1 d . . . . .
H2 H 0.472950 0.433259 0.147966 0.082 Uiso 1 1 calc R U . . .
C3 C 0.6126(2) 0.2844(3) 0.15606(7) 0.0683(6) Uani 1 1 d . . . . .
H3 H 0.616813 0.245857 0.127167 0.082 Uiso 1 1 calc R U . . .
C4 C 0.69269(19) 0.2292(3) 0.18618(6) 0.0689(6) Uani 1 1 d . . . . .
H4 H 0.751396 0.153518 0.177526 0.083 Uiso 1 1 calc R U . . .
C5 C 0.68707(17) 0.2848(3) 0.22917(6) 0.0606(5) Uani 1 1 d . . . . .
H5 H 0.741792 0.246205 0.249324 0.073 Uiso 1 1 calc R U . . .
C6 C 0.59989(17) 0.3982(2) 0.24249(6) 0.0543(5) Uani 1 1 d . . . . .
C7 C 0.59043(19) 0.4601(3) 0.28791(6) 0.0610(5) Uani 1 1 d . . . . .
H7 H 0.532487 0.539227 0.295282 0.073 Uiso 1 1 calc R U . . .
C8 C 0.71103(17) 0.4235(3) 0.39080(6) 0.0607(5) Uani 1 1 d . . . . .
H8 H 0.767917 0.342130 0.383772 0.073 Uiso 1 1 calc R U . . .
C9 C 0.70486(16) 0.4770(3) 0.43319(6) 0.0558(5) Uani 1 1 d . . . . .
H9 H 0.756744 0.429292 0.453202 0.067 Uiso 1 1 calc R U . . .
C10 C 0.62325(15) 0.6022(2) 0.44872(5) 0.0471(4) Uani 1 1 d . . . . .
C11 C 0.61712(14) 0.6469(2) 0.49646(5) 0.0453(4) Uani 1 1 d . . . . .
C12 C 0.68780(17) 0.5690(3) 0.52754(6) 0.0572(5) Uani 1 1 d . . . . .
H12 H 0.741944 0.485979 0.518816 0.069 Uiso 1 1 calc R U . . .
C13 C 0.67874(19) 0.6132(3) 0.57134(6) 0.0671(6) Uani 1 1 d . . . . .
H13 H 0.726713 0.560105 0.591888 0.081 Uiso 1 1 calc R U . . .
C14 C 0.59946(19) 0.7349(3) 0.58457(6) 0.0680(6) Uani 1 1 d . . . . .
H14 H 0.593925 0.765065 0.614053 0.082 Uiso 1 1 calc R U . . .
C15 C 0.52811(19) 0.8125(3) 0.55440(6) 0.0676(6) Uani 1 1 d . . . . .
H15 H 0.474250 0.895451 0.563422 0.081 Uiso 1 1 calc R U . . .
C16 C 0.53619(16) 0.7676(3) 0.51055(6) 0.0569(5) Uani 1 1 d . . . . .
H16 H 0.486607 0.819186 0.490306 0.068 Uiso 1 1 calc R U . . .
H1D H 0.5876(19) 0.565(3) 0.3662(6) 0.078(7) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C10 1.238(2) . ?
N1 N2 1.387(2) . ?
N1 C7 1.257(2) . ?
N2 C8 1.322(2) . ?
N2 H1D 0.96(2) . ?
C1 H1 0.9300 . ?
C1 C2 1.394(2) . ?
C1 C6 1.386(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.358(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.371(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.379(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.390(3) . ?
C6 C7 1.467(2) . ?
C7 H7 0.9300 . ?
C8 H8 0.9300 . ?
C8 C9 1.357(2) . ?
C9 H9 0.9300 . ?
C9 C10 1.425(3) . ?
C10 C11 1.496(2) . ?
C11 C12 1.386(2) . ?
C11 C16 1.382(3) . ?
C12 H12 0.9300 . ?
C12 C13 1.381(2) . ?
C13 H13 0.9300 . ?
C13 C14 1.366(3) . ?
C14 H14 0.9300 . ?
C14 C15 1.370(3) . ?
C15 H15 0.9300 . ?
C15 C16 1.383(3) . ?
C16 H16 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
C7 N1 N2 116.12(18) . . ?
N1 N2 H1D 125.3(12) . . ?
C8 N2 N1 118.63(18) . . ?
C8 N2 H1D 116.0(11) . . ?
C2 C1 H1 120.0 . . ?
C6 C1 H1 120.0 . . ?
C6 C1 C2 120.0(2) . . ?
C1 C2 H2 119.7 . . ?
C3 C2 C1 120.53(19) . . ?
C3 C2 H2 119.7 . . ?
C2 C3 H3 120.1 . . ?
C2 C3 C4 119.90(18) . . ?
C4 C3 H3 120.1 . . ?
C3 C4 H4 119.7 . . ?
C3 C4 C5 120.6(2) . . ?
C5 C4 H4 119.7 . . ?
C4 C5 H5 119.9 . . ?
C4 C5 C6 120.23(19) . . ?
C6 C5 H5 119.9 . . ?
C1 C6 C5 118.66(17) . . ?
C1 C6 C7 119.30(19) . . ?
C5 C6 C7 122.04(18) . . ?
N1 C7 C6 121.17(19) . . ?
N1 C7 H7 119.4 . . ?
C6 C7 H7 119.4 . . ?
N2 C8 H8 117.2 . . ?
N2 C8 C9 125.51(19) . . ?
C9 C8 H8 117.2 . . ?
C8 C9 H9 118.2 . . ?
C8 C9 C10 123.59(17) . . ?
C10 C9 H9 118.2 . . ?
O1 C10 C9 120.53(16) . . ?
O1 C10 C11 118.96(16) . . ?
C9 C10 C11 120.50(16) . . ?
C12 C11 C10 122.62(16) . . ?
C16 C11 C10 119.09(16) . . ?
C16 C11 C12 118.28(16) . . ?
C11 C12 H12 119.6 . . ?
C13 C12 C11 120.73(19) . . ?
C13 C12 H12 119.6 . . ?
C12 C13 H13 119.9 . . ?
C14 C13 C12 120.17(19) . . ?
C14 C13 H13 119.9 . . ?
C13 C14 H14 120.0 . . ?
C13 C14 C15 120.04(18) . . ?
C15 C14 H14 120.0 . . ?
C14 C15 H15 120.0 . . ?
C14 C15 C16 120.02(19) . . ?
C16 C15 H15 120.0 . . ?
C11 C16 C15 120.75(18) . . ?
C11 C16 H16 119.6 . . ?
C15 C16 H16 119.6 . . ?

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 C10 C11 C12 -179.46(17) . . . . ?
O1 C10 C11 C16 2.1(3) . . . . ?
N1 N2 C8 C9 -179.12(18) . . . . ?
N2 N1 C7 C6 179.18(17) . . . . ?
N2 C8 C9 C10 -0.7(3) . . . . ?
C1 C2 C3 C4 -0.3(3) . . . . ?
C1 C6 C7 N1 177.49(19) . . . . ?
C2 C1 C6 C5 0.0(3) . . . . ?
C2 C1 C6 C7 -179.80(18) . . . . ?
C2 C3 C4 C5 0.3(3) . . . . ?
C3 C4 C5 C6 -0.2(3) . . . . ?
C4 C5 C6 C1 0.0(3) . . . . ?
C4 C5 C6 C7 179.79(19) . . . . ?
C5 C6 C7 N1 -2.3(3) . . . . ?
C6 C1 C2 C3 0.2(3) . . . . ?
C7 N1 N2 C8 178.23(18) . . . . ?
C8 C9 C10 O1 -5.1(3) . . . . ?
C8 C9 C10 C11 176.37(18) . . . . ?
C9 C10 C11 C12 -0.9(3) . . . . ?
C9 C10 C11 C16 -179.35(17) . . . . ?
C10 C11 C12 C13 -179.57(17) . . . . ?
C10 C11 C16 C15 -179.84(17) . . . . ?
C11 C12 C13 C14 0.0(3) . . . . ?
C12 C11 C16 C15 1.6(3) . . . . ?
C12 C13 C14 C15 0.5(3) . . . . ?
C13 C14 C15 C16 0.1(3) . . . . ?
C14 C15 C16 C11 -1.1(3) . . . . ?
C16 C11 C12 C13 -1.1(3) . . . . ?

_shelx_SHELXL_version_number     2016/6
_olex2_submission_special_instructions 'No special instructions were received'
