# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_f
_database_code_depnum_ccdc_archive 'CCDC 2021411'
loop_
_audit_author_name
_audit_author_address
'peng zhao'
;Central China Normal University
China
;
_audit_update_record             
;
2020-08-05 deposited with the CCDC.	2020-09-07 downloaded from the CCDC.
;
_audit_creation_date             2019-12-19
_audit_creation_method           
; 
Olex2 1.2 
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506) 
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H17 Br N2 O, C H Cl3'
_chemical_formula_sum            'C23 H18 Br Cl3 N2 O'
_chemical_formula_weight         524.65
_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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 '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      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                   8.4050(19)
_cell_length_b                   10.003(2)
_cell_length_c                   15.623(4)
_cell_angle_alpha                71.488(4)
_cell_angle_beta                 78.914(5)
_cell_angle_gamma                66.772(3)
_cell_volume                     1141.2(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4811
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      29.67
_cell_measurement_theta_min      2.34
_shelx_estimated_absorpt_T_max   0.812
_shelx_estimated_absorpt_T_min   0.781
_exptl_absorpt_coefficient_mu    2.170
_exptl_absorpt_correction_T_max  0.7464
_exptl_absorpt_correction_T_min  0.3146
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS-2008/1 (Bruker,2008)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.527
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0563
_diffrn_reflns_av_unetI/netI     0.0726
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            8078
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.500
_diffrn_reflns_theta_min         1.379
_diffrn_ambient_temperature      273.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_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                3381
_reflns_number_total             4184
_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 v7.68A (Bruker, 2009)'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.667
_refine_diff_density_min         -1.064
_refine_diff_density_rms         0.126
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     273
_refine_ls_number_reflns         4184
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0744
_refine_ls_R_factor_gt           0.0606
_refine_ls_restrained_S_all      1.082
_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)+(0.1090P)²+0.4675P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1644
_refine_ls_wR_factor_ref         0.1799
_refine_special_details          ?
_olex2_refinement_description    
; 
1. Fixed Uiso 
 At 1.2 times of: 
  All C(H) groups, All N(H) groups 
 At 1.5 times of: 
  All C(H,H,H) groups 
2.a Ternary CH refined with riding coordinates: 
 C23(H23) 
2.b Aromatic/amide H refined with riding coordinates: 
 C3(H3), C6(H6), C7(H7), C10(H10), C11(H11), C13(H13), C18(H18), C19(H19), 
 C21(H21), C22(H22), N1(H1) 
2.c Idealised Me refined as rotating group: 
 C1(H1A,H1B,H1C), C15(H15A,H15B,H15C) 
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
_atom_sites_special_details      
; 
The structure was solved using Patterson Methods, followed by a Tangent Expansion (ShelXS). RE = 0.3, Nqual =  -1, Ralpha = 0.04 
;
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 1.12813(6) 0.25234(6) 0.47008(3) 0.0606(2) Uani 1 1 d . . . . .
C1 C -0.3085(6) 0.2604(7) 0.8902(4) 0.0618(13) Uani 1 1 d . . . . .
H1A H -0.2896 0.1707 0.9396 0.093 Uiso 1 1 calc GR . . . .
H1B H -0.3767 0.2592 0.8479 0.093 Uiso 1 1 calc GR . . . .
H1C H -0.3689 0.3476 0.9129 0.093 Uiso 1 1 calc GR . . . .
C2 C -0.1362(5) 0.2666(4) 0.8433(3) 0.0368(8) Uani 1 1 d . . . . .
C3 C 0.0133(4) 0.1994(4) 0.8890(2) 0.0312(7) Uani 1 1 d . . . . .
H3 H 0.0061 0.1517 0.9506 0.037 Uiso 1 1 calc R . . . .
C4 C 0.1735(4) 0.2009(4) 0.8462(2) 0.0267(7) Uani 1 1 d . . . . .
C5 C 0.1859(4) 0.2750(4) 0.7542(2) 0.0269(7) Uani 1 1 d . . . . .
C6 C 0.0341(5) 0.3491(4) 0.7088(2) 0.0351(8) Uani 1 1 d . . . . .
H6 H 0.0388 0.4040 0.6485 0.042 Uiso 1 1 calc R . . . .
C7 C -0.1228(5) 0.3420(5) 0.7524(3) 0.0406(9) Uani 1 1 d . . . . .
H7 H -0.2215 0.3886 0.7202 0.049 Uiso 1 1 calc R . . . .
C8 C 0.3246(4) 0.1260(4) 0.9037(2) 0.0268(7) Uani 1 1 d . . . . .
C9 C 0.4683(4) -0.0591(4) 0.8148(2) 0.0273(7) Uani 1 1 d . . . . .
C10 C 0.4833(6) -0.2109(4) 0.8421(3) 0.0426(9) Uani 1 1 d . . . . .
H10 H 0.4952 -0.2656 0.9025 0.051 Uiso 1 1 calc R . . . .
C11 C 0.4803(6) -0.2780(4) 0.7779(3) 0.0497(11) Uani 1 1 d . . . . .
H11 H 0.4901 -0.3788 0.7961 0.060 Uiso 1 1 calc R . . . .
C12 C 0.4630(5) -0.2002(4) 0.6876(3) 0.0423(9) Uani 1 1 d . . . . .
C13 C 0.4595(5) -0.0546(4) 0.6614(2) 0.0343(8) Uani 1 1 d . . . . .
H13 H 0.4550 -0.0026 0.6004 0.041 Uiso 1 1 calc R . . . .
C14 C 0.4626(4) 0.0181(4) 0.7243(2) 0.0266(7) Uani 1 1 d . . . . .
C15 C 0.4446(7) -0.2714(6) 0.6190(4) 0.0637(13) Uani 1 1 d . . . . .
H15A H 0.5566 -0.3384 0.6024 0.096 Uiso 1 1 calc GR . . . .
H15B H 0.3969 -0.1936 0.5662 0.096 Uiso 1 1 calc GR . . . .
H15C H 0.3687 -0.3272 0.6453 0.096 Uiso 1 1 calc GR . . . .
C16 C 0.4675(4) 0.1738(4) 0.6926(2) 0.0259(7) Uani 1 1 d . . . . .
C17 C 0.6284(4) 0.1916(4) 0.6395(2) 0.0260(7) Uani 1 1 d . . . . .
C18 C 0.7844(5) 0.0706(4) 0.6432(3) 0.0401(9) Uani 1 1 d . . . . .
H18 H 0.7891 -0.0245 0.6795 0.048 Uiso 1 1 calc R . . . .
C19 C 0.9327(5) 0.0887(5) 0.5941(3) 0.0460(9) Uani 1 1 d . . . . .
H19 H 1.0372 0.0071 0.5979 0.055 Uiso 1 1 calc R . . . .
C20 C 0.9238(5) 0.2286(4) 0.5396(2) 0.0374(8) Uani 1 1 d . . . . .
C21 C 0.7718(5) 0.3517(4) 0.5335(2) 0.0349(8) Uani 1 1 d . . . . .
H21 H 0.7684 0.4458 0.4961 0.042 Uiso 1 1 calc R . . . .
C22 C 0.6255(5) 0.3332(4) 0.5836(2) 0.0315(7) Uani 1 1 d . . . . .
H22 H 0.5223 0.4161 0.5805 0.038 Uiso 1 1 calc R . . . .
N1 N 0.4636(4) 0.0120(3) 0.88205(19) 0.0304(6) Uani 1 1 d . . . . .
H1 H 0.5551 -0.0200 0.9105 0.036 Uiso 1 1 calc R . . . .
N2 N 0.3411(4) 0.2914(3) 0.70614(18) 0.0301(6) Uani 1 1 d . . . . .
O1 O 0.3170(3) 0.1639(3) 0.97287(16) 0.0363(6) Uani 1 1 d . . . . .
C23 C 0.9946(6) 0.3056(5) 0.1095(3) 0.0536(11) Uani 1 1 d . . . . .
H23 H 1.0947 0.3005 0.0648 0.064 Uiso 1 1 calc R . . . .
Cl1 Cl 1.0298(3) 0.3596(2) 0.19698(16) 0.1248(8) Uani 1 1 d . . . . .
Cl2 Cl 0.9812(2) 0.12597(13) 0.14910(9) 0.0669(4) Uani 1 1 d . . . . .
Cl3 Cl 0.8102(2) 0.43772(17) 0.05583(13) 0.0891(5) Uani 1 1 d . . . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C20 1.904(4) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C1 C2 1.507(5) . ?
C2 C3 1.383(5) . ?
C2 C7 1.388(6) . ?
C3 H3 0.9300 . ?
C3 C4 1.387(5) . ?
C4 C5 1.398(5) . ?
C4 C8 1.497(4) . ?
C5 C6 1.396(5) . ?
C5 N2 1.416(4) . ?
C6 H6 0.9300 . ?
C6 C7 1.381(5) . ?
C7 H7 0.9300 . ?
C8 N1 1.349(4) . ?
C8 O1 1.238(4) . ?
C9 C10 1.400(5) . ?
C9 C14 1.379(5) . ?
C9 N1 1.431(4) . ?
C10 H10 0.9300 . ?
C10 C11 1.381(6) . ?
C11 H11 0.9300 . ?
C11 C12 1.383(6) . ?
C12 C13 1.372(5) . ?
C12 C15 1.521(5) . ?
C13 H13 0.9300 . ?
C13 C14 1.405(4) . ?
C14 C16 1.492(4) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 C17 1.488(5) . ?
C16 N2 1.282(4) . ?
C17 C18 1.386(5) . ?
C17 C22 1.402(5) . ?
C18 H18 0.9300 . ?
C18 C19 1.377(5) . ?
C19 H19 0.9300 . ?
C19 C20 1.370(6) . ?
C20 C21 1.374(5) . ?
C21 H21 0.9300 . ?
C21 C22 1.370(5) . ?
C22 H22 0.9300 . ?
N1 H1 0.8600 . ?
C23 H23 0.9800 . ?
C23 Cl1 1.731(5) . ?
C23 Cl2 1.747(4) . ?
C23 Cl3 1.742(5) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
C3 C2 C1 121.7(4) . . ?
C3 C2 C7 117.6(3) . . ?
C7 C2 C1 120.7(4) . . ?
C2 C3 H3 118.9 . . ?
C2 C3 C4 122.3(3) . . ?
C4 C3 H3 118.9 . . ?
C3 C4 C5 119.6(3) . . ?
C3 C4 C8 117.0(3) . . ?
C5 C4 C8 123.4(3) . . ?
C4 C5 N2 123.7(3) . . ?
C6 C5 C4 118.4(3) . . ?
C6 C5 N2 117.7(3) . . ?
C5 C6 H6 119.6 . . ?
C7 C6 C5 120.8(3) . . ?
C7 C6 H6 119.6 . . ?
C2 C7 H7 119.4 . . ?
C6 C7 C2 121.3(3) . . ?
C6 C7 H7 119.4 . . ?
N1 C8 C4 119.4(3) . . ?
O1 C8 C4 119.7(3) . . ?
O1 C8 N1 120.8(3) . . ?
C10 C9 N1 118.8(3) . . ?
C14 C9 C10 120.1(3) . . ?
C14 C9 N1 121.1(3) . . ?
C9 C10 H10 120.5 . . ?
C11 C10 C9 119.0(3) . . ?
C11 C10 H10 120.5 . . ?
C10 C11 H11 119.0 . . ?
C10 C11 C12 122.1(3) . . ?
C12 C11 H11 119.0 . . ?
C11 C12 C15 121.5(4) . . ?
C13 C12 C11 117.9(3) . . ?
C13 C12 C15 120.6(4) . . ?
C12 C13 H13 119.1 . . ?
C12 C13 C14 121.8(3) . . ?
C14 C13 H13 119.1 . . ?
C9 C14 C13 118.9(3) . . ?
C9 C14 C16 121.0(3) . . ?
C13 C14 C16 120.1(3) . . ?
C12 C15 H15A 109.5 . . ?
C12 C15 H15B 109.5 . . ?
C12 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C17 C16 C14 116.9(3) . . ?
N2 C16 C14 124.1(3) . . ?
N2 C16 C17 118.9(3) . . ?
C18 C17 C16 121.7(3) . . ?
C18 C17 C22 118.0(3) . . ?
C22 C17 C16 120.3(3) . . ?
C17 C18 H18 119.4 . . ?
C19 C18 C17 121.2(3) . . ?
C19 C18 H18 119.4 . . ?
C18 C19 H19 120.5 . . ?
C20 C19 C18 119.0(4) . . ?
C20 C19 H19 120.5 . . ?
C19 C20 Br1 118.8(3) . . ?
C19 C20 C21 121.9(4) . . ?
C21 C20 Br1 119.3(3) . . ?
C20 C21 H21 120.6 . . ?
C22 C21 C20 118.8(3) . . ?
C22 C21 H21 120.6 . . ?
C17 C22 H22 119.4 . . ?
C21 C22 C17 121.2(3) . . ?
C21 C22 H22 119.4 . . ?
C8 N1 C9 124.2(3) . . ?
C8 N1 H1 117.9 . . ?
C9 N1 H1 117.9 . . ?
C16 N2 C5 118.9(3) . . ?
Cl1 C23 H23 107.9 . . ?
Cl1 C23 Cl2 110.5(3) . . ?
Cl1 C23 Cl3 111.2(3) . . ?
Cl2 C23 H23 107.9 . . ?
Cl3 C23 H23 107.9 . . ?
Cl3 C23 Cl2 111.3(3) . . ?

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
N1 H1 O1 0.86 2.10 2.855(4) 146.1 2_657

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 C20 C21 C22 179.8(3) . . . . ?
C1 C2 C3 C4 178.3(4) . . . . ?
C1 C2 C7 C6 179.6(4) . . . . ?
C2 C3 C4 C5 1.4(5) . . . . ?
C2 C3 C4 C8 179.2(3) . . . . ?
C3 C2 C7 C6 0.4(5) . . . . ?
C3 C4 C5 C6 1.7(5) . . . . ?
C3 C4 C5 N2 175.6(3) . . . . ?
C3 C4 C8 N1 121.9(3) . . . . ?
C3 C4 C8 O1 -54.3(4) . . . . ?
C4 C5 C6 C7 -3.7(5) . . . . ?
C4 C5 N2 C16 68.1(4) . . . . ?
C4 C8 N1 C9 -9.5(5) . . . . ?
C5 C4 C8 N1 -60.3(4) . . . . ?
C5 C4 C8 O1 123.4(4) . . . . ?
C5 C6 C7 C2 2.7(6) . . . . ?
C6 C5 N2 C16 -118.0(3) . . . . ?
C7 C2 C3 C4 -2.4(5) . . . . ?
C8 C4 C5 C6 -175.9(3) . . . . ?
C8 C4 C5 N2 -2.1(5) . . . . ?
C9 C10 C11 C12 0.1(7) . . . . ?
C9 C14 C16 C17 109.8(3) . . . . ?
C9 C14 C16 N2 -72.2(4) . . . . ?
C10 C9 C14 C13 4.5(5) . . . . ?
C10 C9 C14 C16 -172.8(3) . . . . ?
C10 C9 N1 C8 -114.3(4) . . . . ?
C10 C11 C12 C13 4.0(6) . . . . ?
C10 C11 C12 C15 -174.8(4) . . . . ?
C11 C12 C13 C14 -3.8(6) . . . . ?
C12 C13 C14 C9 -0.4(5) . . . . ?
C12 C13 C14 C16 176.9(3) . . . . ?
C13 C14 C16 C17 -67.4(4) . . . . ?
C13 C14 C16 N2 110.6(4) . . . . ?
C14 C9 C10 C11 -4.4(6) . . . . ?
C14 C9 N1 C8 67.3(5) . . . . ?
C14 C16 C17 C18 -20.2(4) . . . . ?
C14 C16 C17 C22 159.6(3) . . . . ?
C14 C16 N2 C5 0.1(4) . . . . ?
C15 C12 C13 C14 174.9(4) . . . . ?
C16 C17 C18 C19 -179.7(3) . . . . ?
C16 C17 C22 C21 -179.3(3) . . . . ?
C17 C16 N2 C5 178.0(3) . . . . ?
C17 C18 C19 C20 -1.2(6) . . . . ?
C18 C17 C22 C21 0.5(5) . . . . ?
C18 C19 C20 Br1 -178.9(3) . . . . ?
C18 C19 C20 C21 0.9(6) . . . . ?
C19 C20 C21 C22 0.0(6) . . . . ?
C20 C21 C22 C17 -0.7(5) . . . . ?
C22 C17 C18 C19 0.5(5) . . . . ?
N1 C9 C10 C11 177.2(4) . . . . ?
N1 C9 C14 C13 -177.1(3) . . . . ?
N1 C9 C14 C16 5.6(5) . . . . ?
N2 C5 C6 C7 -178.0(3) . . . . ?
N2 C16 C17 C18 161.7(3) . . . . ?
N2 C16 C17 C22 -18.5(4) . . . . ?
O1 C8 N1 C9 166.7(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_y
_database_code_depnum_ccdc_archive 'CCDC 2021412'
loop_
_audit_author_name
_audit_author_address
'peng zhao'
;Central China Normal University
China
;
_audit_update_record             
;
2020-08-05 deposited with the CCDC.	2020-09-07 downloaded from the CCDC.
;
_audit_creation_date             2019-12-19
_audit_creation_method           
; 
Olex2 1.2 
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506) 
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H18 N2 O'
_chemical_formula_sum            'C22 H18 N2 O'
_chemical_formula_weight         326.38
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   13.602(3)
_cell_length_b                   13.685(3)
_cell_length_c                   19.401(4)
_cell_angle_alpha                90
_cell_angle_beta                 99.361(3)
_cell_angle_gamma                90
_cell_volume                     3563.2(12)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    6724
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      31.22
_cell_measurement_theta_min      2.26
_shelx_estimated_absorpt_T_max   0.989
_shelx_estimated_absorpt_T_min   0.985
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_T_max  0.7463
_exptl_absorpt_correction_T_min  0.6687
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS-2008/1 (Bruker,2008)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.217
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1376
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0399
_diffrn_reflns_av_unetI/netI     0.0343
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            12571
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.500
_diffrn_reflns_theta_min         2.125
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_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                2732
_reflns_number_total             3323
_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 v7.68A (Bruker, 2009)'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.259
_refine_diff_density_min         -0.189
_refine_diff_density_rms         0.042
_refine_ls_extinction_coef       0.0103(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     229
_refine_ls_number_reflns         3323
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0592
_refine_ls_R_factor_gt           0.0486
_refine_ls_restrained_S_all      1.057
_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)+(0.0825P)²+2.1671P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1408
_refine_ls_wR_factor_ref         0.1557
_refine_special_details          ?
_olex2_refinement_description    
; 
1. Fixed Uiso 
 At 1.2 times of: 
  All C(H) groups, All N(H) groups 
 At 1.5 times of: 
  All C(H,H,H) groups 
2.a Aromatic/amide H refined with riding coordinates: 
 C3(H3), C4(H4), C7(H7), C10(H10), C12(H12), C13(H13), C18(H18), C19(H19), 
 C20(H20), C21(H21), C22(H22), N1(H1) 
2.b Idealised Me refined as rotating group: 
 C1(H1A,H1B,H1C), C15(H15A,H15B,H15C) 
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
_atom_sites_special_details      
; 
The structure was solved using Direct Methods (ShelXS). RE = 0.2, Nqual =  -1, Ralpha = 0.034 
;
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.64194(16) 0.54293(16) 0.30753(12) 0.0646(6) Uani 1 1 d . . . . .
H1A H 0.6585 0.4798 0.3276 0.097 Uiso 1 1 calc GR . . . .
H1B H 0.7003 0.5835 0.3140 0.097 Uiso 1 1 calc GR . . . .
H1C H 0.6174 0.5359 0.2585 0.097 Uiso 1 1 calc GR . . . .
C2 C 0.56287(13) 0.58943(12) 0.34284(9) 0.0454(4) Uani 1 1 d . . . . .
C3 C 0.50023(16) 0.53421(13) 0.37699(11) 0.0594(5) Uani 1 1 d . . . . .
H3 H 0.5093 0.4669 0.3804 0.071 Uiso 1 1 calc R . . . .
C4 C 0.42444(16) 0.57701(13) 0.40608(12) 0.0563(5) Uani 1 1 d . . . . .
H4 H 0.3825 0.5383 0.4280 0.068 Uiso 1 1 calc R . . . .
C5 C 0.41077(12) 0.67746(12) 0.40264(8) 0.0388(4) Uani 1 1 d . . . . .
C6 C 0.47585(11) 0.73498(11) 0.37236(8) 0.0346(4) Uani 1 1 d . . . . .
C7 C 0.55019(12) 0.68995(12) 0.34191(9) 0.0392(4) Uani 1 1 d . . . . .
H7 H 0.5925 0.7286 0.3203 0.047 Uiso 1 1 calc R . . . .
C8 C 0.25541(12) 0.77069(12) 0.39540(9) 0.0405(4) Uani 1 1 d . . . . .
C9 C 0.25483(12) 0.79100(13) 0.31923(9) 0.0432(4) Uani 1 1 d . . . . .
C10 C 0.17513(14) 0.75648(17) 0.27152(11) 0.0604(5) Uani 1 1 d . . . . .
H10 H 0.1290 0.7151 0.2870 0.072 Uiso 1 1 calc R . . . .
C11 C 0.16231(16) 0.7822(2) 0.20110(12) 0.0731(7) Uani 1 1 d . . . . .
C12 C 0.22919(18) 0.8469(2) 0.18043(11) 0.0737(7) Uani 1 1 d . . . . .
H12 H 0.2214 0.8661 0.1339 0.088 Uiso 1 1 calc R . . . .
C13 C 0.30704(15) 0.88361(16) 0.22686(10) 0.0580(5) Uani 1 1 d . . . . .
H13 H 0.3496 0.9291 0.2116 0.070 Uiso 1 1 calc R . . . .
C14 C 0.32363(12) 0.85409(12) 0.29647(9) 0.0424(4) Uani 1 1 d . . . . .
C15 C 0.0765(2) 0.7405(3) 0.15008(17) 0.1246(15) Uani 1 1 d . . . . .
H15A H 0.0741 0.6710 0.1560 0.187 Uiso 1 1 calc GR . . . .
H15B H 0.0858 0.7553 0.1032 0.187 Uiso 1 1 calc GR . . . .
H15C H 0.0151 0.7689 0.1587 0.187 Uiso 1 1 calc GR . . . .
C16 C 0.47147(12) 0.84456(11) 0.37634(8) 0.0374(4) Uani 1 1 d . . . . .
C17 C 0.55418(13) 0.89382(12) 0.42312(9) 0.0420(4) Uani 1 1 d . . . . .
C18 C 0.56394(16) 0.99521(13) 0.42074(11) 0.0584(5) Uani 1 1 d . . . . .
H18 H 0.5187 1.0318 0.3900 0.070 Uiso 1 1 calc R . . . .
C19 C 0.64103(19) 1.04148(17) 0.46423(13) 0.0736(7) Uani 1 1 d . . . . .
H19 H 0.6472 1.1090 0.4621 0.088 Uiso 1 1 calc R . . . .
C20 C 0.70787(18) 0.98944(18) 0.51004(13) 0.0713(7) Uani 1 1 d . . . . .
H20 H 0.7594 1.0213 0.5387 0.086 Uiso 1 1 calc R . . . .
C21 C 0.69859(17) 0.89030(18) 0.51352(12) 0.0681(6) Uani 1 1 d . . . . .
H21 H 0.7437 0.8546 0.5449 0.082 Uiso 1 1 calc R . . . .
C22 C 0.62190(14) 0.84248(14) 0.47022(10) 0.0536(5) Uani 1 1 d . . . . .
H22 H 0.6162 0.7749 0.4731 0.064 Uiso 1 1 calc R . . . .
N1 N 0.33162(11) 0.72125(10) 0.43185(7) 0.0430(4) Uani 1 1 d . . . . .
H1 H 0.3330 0.7155 0.4761 0.052 Uiso 1 1 calc R . . . .
N2 N 0.40314(11) 0.89729(10) 0.34179(8) 0.0435(4) Uani 1 1 d . . . . .
O1 O 0.18422(9) 0.79883(9) 0.42266(7) 0.0505(4) Uani 1 1 d . . . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C1 C2 1.507(2) . ?
C2 C3 1.386(3) . ?
C2 C7 1.386(2) . ?
C3 H3 0.9300 . ?
C3 C4 1.383(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.387(2) . ?
C5 C6 1.385(2) . ?
C5 N1 1.427(2) . ?
C6 C7 1.395(2) . ?
C6 C16 1.503(2) . ?
C7 H7 0.9300 . ?
C8 C9 1.502(2) . ?
C8 N1 1.339(2) . ?
C8 O1 1.2378(19) . ?
C9 C10 1.389(3) . ?
C9 C14 1.397(2) . ?
C10 H10 0.9300 . ?
C10 C11 1.394(3) . ?
C11 C12 1.375(4) . ?
C11 C15 1.514(4) . ?
C12 H12 0.9300 . ?
C12 C13 1.369(3) . ?
C13 H13 0.9300 . ?
C13 C14 1.392(3) . ?
C14 N2 1.408(2) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 C17 1.487(2) . ?
C16 N2 1.277(2) . ?
C17 C18 1.395(2) . ?
C17 C22 1.380(3) . ?
C18 H18 0.9300 . ?
C18 C19 1.387(3) . ?
C19 H19 0.9300 . ?
C19 C20 1.364(4) . ?
C20 H20 0.9300 . ?
C20 C21 1.365(3) . ?
C21 H21 0.9300 . ?
C21 C22 1.392(3) . ?
C22 H22 0.9300 . ?
N1 H1 0.8600 . ?

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
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
C3 C2 C1 121.80(17) . . ?
C3 C2 C7 117.55(15) . . ?
C7 C2 C1 120.65(17) . . ?
C2 C3 H3 119.3 . . ?
C4 C3 C2 121.41(16) . . ?
C4 C3 H3 119.3 . . ?
C3 C4 H4 119.9 . . ?
C3 C4 C5 120.19(16) . . ?
C5 C4 H4 119.9 . . ?
C4 C5 N1 120.05(15) . . ?
C6 C5 C4 119.59(15) . . ?
C6 C5 N1 120.34(14) . . ?
C5 C6 C7 119.08(14) . . ?
C5 C6 C16 120.80(13) . . ?
C7 C6 C16 119.99(14) . . ?
C2 C7 C6 122.02(15) . . ?
C2 C7 H7 119.0 . . ?
C6 C7 H7 119.0 . . ?
N1 C8 C9 119.50(14) . . ?
O1 C8 C9 118.91(15) . . ?
O1 C8 N1 121.58(15) . . ?
C10 C9 C8 118.12(16) . . ?
C10 C9 C14 119.34(17) . . ?
C14 C9 C8 121.92(15) . . ?
C9 C10 H10 119.1 . . ?
C9 C10 C11 121.8(2) . . ?
C11 C10 H10 119.1 . . ?
C10 C11 C15 120.4(3) . . ?
C12 C11 C10 117.7(2) . . ?
C12 C11 C15 121.9(3) . . ?
C11 C12 H12 119.3 . . ?
C13 C12 C11 121.5(2) . . ?
C13 C12 H12 119.3 . . ?
C12 C13 H13 119.4 . . ?
C12 C13 C14 121.2(2) . . ?
C14 C13 H13 119.4 . . ?
C9 C14 N2 123.25(15) . . ?
C13 C14 C9 118.35(18) . . ?
C13 C14 N2 118.07(17) . . ?
C11 C15 H15A 109.5 . . ?
C11 C15 H15B 109.5 . . ?
C11 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C17 C16 C6 116.82(14) . . ?
N2 C16 C6 124.63(15) . . ?
N2 C16 C17 118.54(14) . . ?
C18 C17 C16 119.81(17) . . ?
C22 C17 C16 122.05(15) . . ?
C22 C17 C18 118.13(17) . . ?
C17 C18 H18 120.0 . . ?
C19 C18 C17 120.0(2) . . ?
C19 C18 H18 120.0 . . ?
C18 C19 H19 119.5 . . ?
C20 C19 C18 121.0(2) . . ?
C20 C19 H19 119.5 . . ?
C19 C20 H20 120.2 . . ?
C19 C20 C21 119.6(2) . . ?
C21 C20 H20 120.2 . . ?
C20 C21 H21 119.9 . . ?
C20 C21 C22 120.2(2) . . ?
C22 C21 H21 119.9 . . ?
C17 C22 C21 120.96(19) . . ?
C17 C22 H22 119.5 . . ?
C21 C22 H22 119.5 . . ?
C5 N1 H1 117.6 . . ?
C8 N1 C5 124.85(14) . . ?
C8 N1 H1 117.6 . . ?
C16 N2 C14 120.65(14) . . ?

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
C1 C2 C3 C4 -176.5(2) . . . . ?
C1 C2 C7 C6 178.13(16) . . . . ?
C2 C3 C4 C5 -1.2(3) . . . . ?
C3 C2 C7 C6 -1.6(3) . . . . ?
C3 C4 C5 C6 -2.5(3) . . . . ?
C3 C4 C5 N1 179.12(18) . . . . ?
C4 C5 C6 C7 4.0(2) . . . . ?
C4 C5 C6 C16 -171.78(17) . . . . ?
C4 C5 N1 C8 -117.3(2) . . . . ?
C5 C6 C7 C2 -2.0(2) . . . . ?
C5 C6 C16 C17 108.25(17) . . . . ?
C5 C6 C16 N2 -72.9(2) . . . . ?
C6 C5 N1 C8 64.4(2) . . . . ?
C6 C16 C17 C18 169.44(15) . . . . ?
C6 C16 C17 C22 -11.5(2) . . . . ?
C6 C16 N2 C14 0.8(2) . . . . ?
C7 C2 C3 C4 3.2(3) . . . . ?
C7 C6 C16 C17 -67.54(19) . . . . ?
C7 C6 C16 N2 111.31(18) . . . . ?
C8 C9 C10 C11 171.90(17) . . . . ?
C8 C9 C14 C13 -168.00(15) . . . . ?
C8 C9 C14 N2 5.2(2) . . . . ?
C9 C8 N1 C5 -5.8(2) . . . . ?
C9 C10 C11 C12 -2.8(3) . . . . ?
C9 C10 C11 C15 178.0(2) . . . . ?
C9 C14 N2 C16 63.0(2) . . . . ?
C10 C9 C14 C13 2.8(2) . . . . ?
C10 C9 C14 N2 176.04(15) . . . . ?
C10 C11 C12 C13 1.3(3) . . . . ?
C11 C12 C13 C14 2.3(3) . . . . ?
C12 C13 C14 C9 -4.4(3) . . . . ?
C12 C13 C14 N2 -177.94(16) . . . . ?
C13 C14 N2 C16 -123.81(17) . . . . ?
C14 C9 C10 C11 0.7(3) . . . . ?
C15 C11 C12 C13 -179.5(2) . . . . ?
C16 C6 C7 C2 173.89(16) . . . . ?
C16 C17 C18 C19 -179.94(16) . . . . ?
C16 C17 C22 C21 -179.90(17) . . . . ?
C17 C16 N2 C14 179.59(13) . . . . ?
C17 C18 C19 C20 -0.4(3) . . . . ?
C18 C17 C22 C21 -0.8(3) . . . . ?
C18 C19 C20 C21 -0.4(3) . . . . ?
C19 C20 C21 C22 0.5(3) . . . . ?
C20 C21 C22 C17 0.1(3) . . . . ?
C22 C17 C18 C19 1.0(3) . . . . ?
N1 C5 C6 C7 -177.61(15) . . . . ?
N1 C5 C6 C16 6.6(2) . . . . ?
N1 C8 C9 C10 121.51(18) . . . . ?
N1 C8 C9 C14 -67.6(2) . . . . ?
N2 C16 C17 C18 -9.5(2) . . . . ?
N2 C16 C17 C22 169.57(16) . . . . ?
O1 C8 C9 C10 -57.3(2) . . . . ?
O1 C8 C9 C14 113.65(18) . . . . ?
O1 C8 N1 C5 172.97(15) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
