# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2021

####################################################################### 
# 
# 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 
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data_201127d_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2052427'
loop_
_audit_author_name
_audit_author_address
qianbaiyang
;AnHui Normal University
China
;
_audit_update_record             
;
2020-12-25 deposited with the CCDC.	2021-03-25 downloaded from the CCDC.
;
_audit_creation_date             2020-12-03
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H20 N2 O'
_chemical_formula_sum            'C22 H20 N2 O'
_chemical_formula_weight         328.40
_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      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                   7.7527(8)
_cell_length_b                   10.2814(11)
_cell_length_c                   11.9759(12)
_cell_angle_alpha                67.0030(10)
_cell_angle_beta                 78.8430(10)
_cell_angle_gamma                83.4520(10)
_cell_volume                     861.33(15)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3260
_cell_measurement_temperature    300
_cell_measurement_theta_max      27.536
_cell_measurement_theta_min      2.257
_shelx_estimated_absorpt_T_max   0.985
_shelx_estimated_absorpt_T_min   0.982
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.6190
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.1026 before and 0.0490 after correction. The Ratio of minimum to maximum transmission is 0.8303. The λ/2 correction factor is 0.00150.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.266
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             348
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0286
_diffrn_reflns_av_unetI/netI     0.0419
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            10207
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.616
_diffrn_reflns_theta_min         1.872
_diffrn_ambient_temperature      300
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.986
_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                2676
_reflns_number_total             3938
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.203
_refine_diff_density_min         -0.194
_refine_diff_density_rms         0.036
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         3938
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0798
_refine_ls_R_factor_gt           0.0524
_refine_ls_restrained_S_all      1.038
_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)+(0.0592P)²+0.1482P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1248
_refine_ls_wR_factor_ref         0.1396
_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:
 C18(H18A,H18B), C19(H19A,H19B), C21(H21A,H21B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C4(H4), C5(H5), C6(H6), C7(H7), C10(H10), C11(H11), C12(H12),
 C15(H15), C16(H16), C17(H17)
2.c Idealised Me refined as rotating group:
 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
O1 O 0.1770(2) 0.81072(14) 0.28387(14) 0.0870(5) Uani 1 1 d . . . . .
N1 N 0.26836(18) 0.55699(13) 0.73006(12) 0.0411(3) Uani 1 1 d . . . . .
N2 N 0.55789(19) 0.72705(15) 0.64547(13) 0.0483(4) Uani 1 1 d . . . . .
C1 C 0.2671(2) 0.51603(16) 0.63240(14) 0.0389(4) Uani 1 1 d . . . . .
C2 C 0.2950(2) 0.37331(16) 0.67195(15) 0.0441(4) Uani 1 1 d . . . . .
H2 H 0.298970 0.318981 0.624945 0.053 Uiso 1 1 calc R . . . .
C3 C 0.3174(2) 0.32093(16) 0.79789(15) 0.0415(4) Uani 1 1 d . . . . .
C4 C 0.3485(2) 0.18719(17) 0.88811(17) 0.0514(4) Uani 1 1 d . . . . .
H4 H 0.358907 0.106498 0.869638 0.062 Uiso 1 1 calc R . . . .
C5 C 0.3632(3) 0.17704(19) 1.00359(17) 0.0570(5) Uani 1 1 d . . . . .
H5 H 0.383044 0.088581 1.063324 0.068 Uiso 1 1 calc R . . . .
C6 C 0.3490(3) 0.2965(2) 1.03326(17) 0.0576(5) Uani 1 1 d . . . . .
H6 H 0.360851 0.286314 1.112086 0.069 Uiso 1 1 calc R . . . .
C7 C 0.3178(2) 0.42907(19) 0.94815(16) 0.0517(4) Uani 1 1 d . . . . .
H7 H 0.308496 0.508932 0.967745 0.062 Uiso 1 1 calc R . . . .
C8 C 0.3008(2) 0.43896(16) 0.83172(14) 0.0396(4) Uani 1 1 d . . . . .
C9 C 0.2502(2) 0.69850(15) 0.72636(14) 0.0392(4) Uani 1 1 d . . . . .
C10 C 0.0907(2) 0.75097(18) 0.76406(16) 0.0481(4) Uani 1 1 d . . . . .
H10 H -0.006267 0.694556 0.791181 0.058 Uiso 1 1 calc R . . . .
C11 C 0.0699(3) 0.88921(19) 0.76276(17) 0.0527(5) Uani 1 1 d . . . . .
H11 H -0.040564 0.924482 0.787061 0.063 Uiso 1 1 calc R . . . .
C12 C 0.2113(3) 0.97072(17) 0.72599(16) 0.0502(5) Uani 1 1 d . . . . .
H12 H 0.197015 1.061834 0.725831 0.060 Uiso 1 1 calc R . . . .
C13 C 0.3801(2) 0.91983(16) 0.68787(14) 0.0422(4) Uani 1 1 d . . . . .
C14 C 0.4006(2) 0.78191(15) 0.68532(13) 0.0382(4) Uani 1 1 d . . . . .
C15 C 0.5322(3) 0.99873(18) 0.65096(16) 0.0535(5) Uani 1 1 d . . . . .
H15 H 0.525599 1.088599 0.653187 0.064 Uiso 1 1 calc R . . . .
C16 C 0.6877(3) 0.9437(2) 0.61234(18) 0.0595(5) Uani 1 1 d . . . . .
H16 H 0.789133 0.994852 0.587781 0.071 Uiso 1 1 calc R . . . .
C17 C 0.6936(3) 0.8079(2) 0.60991(18) 0.0572(5) Uani 1 1 d . . . . .
H17 H 0.801272 0.772572 0.581090 0.069 Uiso 1 1 calc R . . . .
C18 C 0.2384(3) 0.62567(17) 0.51180(15) 0.0476(4) Uani 1 1 d . . . . .
H18A H 0.331717 0.692015 0.483498 0.057 Uiso 1 1 calc R . . . .
H18B H 0.128376 0.677424 0.524032 0.057 Uiso 1 1 calc R . . . .
C19 C 0.2324(2) 0.57326(17) 0.41229(15) 0.0439(4) Uani 1 1 d . . . . .
H19A H 0.141149 0.505119 0.440493 0.053 Uiso 1 1 calc R . . . .
H19B H 0.343832 0.524751 0.396965 0.053 Uiso 1 1 calc R . . . .
C20 C 0.1972(2) 0.68905(18) 0.29371(16) 0.0476(4) Uani 1 1 d . . . . .
C21 C 0.1892(3) 0.6460(2) 0.18927(17) 0.0598(5) Uani 1 1 d . . . . .
H21A H 0.098489 0.577784 0.215290 0.072 Uiso 1 1 calc R . . . .
H21B H 0.300548 0.598933 0.171150 0.072 Uiso 1 1 calc R . . . .
C22 C 0.1521(3) 0.7651(3) 0.07299(19) 0.0781(7) Uani 1 1 d . . . . .
H22A H 0.139190 0.727321 0.013490 0.117 Uiso 1 1 calc GR . . . .
H22B H 0.248028 0.827862 0.040810 0.117 Uiso 1 1 calc GR . . . .
H22C H 0.045574 0.816127 0.090457 0.117 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C20 1.204(2) . ?
N1 C1 1.3913(19) . ?
N1 C8 1.3829(19) . ?
N1 C9 1.4296(19) . ?
N2 C14 1.364(2) . ?
N2 C17 1.315(2) . ?
C1 C2 1.360(2) . ?
C1 C18 1.484(2) . ?
C2 H2 0.9300 . ?
C2 C3 1.428(2) . ?
C3 C4 1.407(2) . ?
C3 C8 1.408(2) . ?
C4 H4 0.9300 . ?
C4 C5 1.372(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.393(3) . ?
C6 H6 0.9300 . ?
C6 C7 1.375(2) . ?
C7 H7 0.9300 . ?
C7 C8 1.389(2) . ?
C9 C10 1.358(2) . ?
C9 C14 1.419(2) . ?
C10 H10 0.9300 . ?
C10 C11 1.406(2) . ?
C11 H11 0.9300 . ?
C11 C12 1.354(3) . ?
C12 H12 0.9300 . ?
C12 C13 1.412(2) . ?
C13 C14 1.420(2) . ?
C13 C15 1.408(2) . ?
C15 H15 0.9300 . ?
C15 C16 1.349(3) . ?
C16 H16 0.9300 . ?
C16 C17 1.403(3) . ?
C17 H17 0.9300 . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C18 C19 1.497(2) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C19 C20 1.504(2) . ?
C20 C21 1.494(2) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C21 C22 1.504(3) . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C9 126.38(13) . . ?
C8 N1 C1 109.15(12) . . ?
C8 N1 C9 124.37(13) . . ?
C17 N2 C14 116.72(15) . . ?
N1 C1 C18 119.04(13) . . ?
C2 C1 N1 108.35(14) . . ?
C2 C1 C18 132.61(15) . . ?
C1 C2 H2 125.8 . . ?
C1 C2 C3 108.45(14) . . ?
C3 C2 H2 125.8 . . ?
C4 C3 C2 135.71(15) . . ?
C4 C3 C8 117.72(15) . . ?
C8 C3 C2 106.56(13) . . ?
C3 C4 H4 120.3 . . ?
C5 C4 C3 119.34(16) . . ?
C5 C4 H4 120.3 . . ?
C4 C5 H5 119.3 . . ?
C4 C5 C6 121.38(17) . . ?
C6 C5 H5 119.3 . . ?
C5 C6 H6 119.4 . . ?
C7 C6 C5 121.22(17) . . ?
C7 C6 H6 119.4 . . ?
C6 C7 H7 121.3 . . ?
C6 C7 C8 117.32(16) . . ?
C8 C7 H7 121.3 . . ?
N1 C8 C3 107.47(14) . . ?
N1 C8 C7 129.53(14) . . ?
C7 C8 C3 123.00(15) . . ?
C10 C9 N1 120.01(15) . . ?
C10 C9 C14 120.65(14) . . ?
C14 C9 N1 119.33(14) . . ?
C9 C10 H10 119.5 . . ?
C9 C10 C11 121.07(17) . . ?
C11 C10 H10 119.5 . . ?
C10 C11 H11 120.1 . . ?
C12 C11 C10 119.74(17) . . ?
C12 C11 H11 120.1 . . ?
C11 C12 H12 119.4 . . ?
C11 C12 C13 121.15(15) . . ?
C13 C12 H12 119.4 . . ?
C12 C13 C14 119.26(15) . . ?
C15 C13 C12 123.64(15) . . ?
C15 C13 C14 117.10(16) . . ?
N2 C14 C9 119.11(14) . . ?
N2 C14 C13 122.81(15) . . ?
C9 C14 C13 118.08(14) . . ?
C13 C15 H15 120.1 . . ?
C16 C15 C13 119.86(17) . . ?
C16 C15 H15 120.1 . . ?
C15 C16 H16 120.6 . . ?
C15 C16 C17 118.78(18) . . ?
C17 C16 H16 120.6 . . ?
N2 C17 C16 124.69(18) . . ?
N2 C17 H17 117.7 . . ?
C16 C17 H17 117.7 . . ?
C1 C18 H18A 108.3 . . ?
C1 C18 H18B 108.3 . . ?
C1 C18 C19 116.05(13) . . ?
H18A C18 H18B 107.4 . . ?
C19 C18 H18A 108.3 . . ?
C19 C18 H18B 108.3 . . ?
C18 C19 H19A 108.9 . . ?
C18 C19 H19B 108.9 . . ?
C18 C19 C20 113.40(14) . . ?
H19A C19 H19B 107.7 . . ?
C20 C19 H19A 108.9 . . ?
C20 C19 H19B 108.9 . . ?
O1 C20 C19 121.23(16) . . ?
O1 C20 C21 121.82(17) . . ?
C21 C20 C19 116.95(15) . . ?
C20 C21 H21A 108.5 . . ?
C20 C21 H21B 108.5 . . ?
C20 C21 C22 115.07(17) . . ?
H21A C21 H21B 107.5 . . ?
C22 C21 H21A 108.5 . . ?
C22 C21 H21B 108.5 . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
C21 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
O1 C20 C21 C22 -0.8(3) . . . . ?
N1 C1 C2 C3 -0.81(19) . . . . ?
N1 C1 C18 C19 -177.93(14) . . . . ?
N1 C9 C10 C11 179.19(15) . . . . ?
N1 C9 C14 N2 2.7(2) . . . . ?
N1 C9 C14 C13 -177.21(13) . . . . ?
C1 N1 C8 C3 -0.98(17) . . . . ?
C1 N1 C8 C7 178.35(17) . . . . ?
C1 N1 C9 C10 97.2(2) . . . . ?
C1 N1 C9 C14 -84.0(2) . . . . ?
C1 C2 C3 C4 179.62(19) . . . . ?
C1 C2 C3 C8 0.21(19) . . . . ?
C1 C18 C19 C20 178.15(14) . . . . ?
C2 C1 C18 C19 2.3(3) . . . . ?
C2 C3 C4 C5 179.93(18) . . . . ?
C2 C3 C8 N1 0.47(17) . . . . ?
C2 C3 C8 C7 -178.91(16) . . . . ?
C3 C4 C5 C6 -0.4(3) . . . . ?
C4 C3 C8 N1 -179.07(15) . . . . ?
C4 C3 C8 C7 1.5(2) . . . . ?
C4 C5 C6 C7 0.7(3) . . . . ?
C5 C6 C7 C8 0.1(3) . . . . ?
C6 C7 C8 N1 179.52(16) . . . . ?
C6 C7 C8 C3 -1.2(3) . . . . ?
C8 N1 C1 C2 1.12(18) . . . . ?
C8 N1 C1 C18 -178.73(14) . . . . ?
C8 N1 C9 C10 -86.8(2) . . . . ?
C8 N1 C9 C14 91.96(18) . . . . ?
C8 C3 C4 C5 -0.7(3) . . . . ?
C9 N1 C1 C2 177.59(15) . . . . ?
C9 N1 C1 C18 -2.3(2) . . . . ?
C9 N1 C8 C3 -177.54(14) . . . . ?
C9 N1 C8 C7 1.8(3) . . . . ?
C9 C10 C11 C12 -1.5(3) . . . . ?
C10 C9 C14 N2 -178.53(14) . . . . ?
C10 C9 C14 C13 1.6(2) . . . . ?
C10 C11 C12 C13 0.4(3) . . . . ?
C11 C12 C13 C14 1.6(2) . . . . ?
C11 C12 C13 C15 -178.75(16) . . . . ?
C12 C13 C14 N2 177.57(14) . . . . ?
C12 C13 C14 C9 -2.5(2) . . . . ?
C12 C13 C15 C16 -178.03(16) . . . . ?
C13 C15 C16 C17 0.0(3) . . . . ?
C14 N2 C17 C16 1.2(3) . . . . ?
C14 C9 C10 C11 0.4(2) . . . . ?
C14 C13 C15 C16 1.7(2) . . . . ?
C15 C13 C14 N2 -2.1(2) . . . . ?
C15 C13 C14 C9 177.77(14) . . . . ?
C15 C16 C17 N2 -1.6(3) . . . . ?
C17 N2 C14 C9 -179.15(15) . . . . ?
C17 N2 C14 C13 0.8(2) . . . . ?
C18 C1 C2 C3 179.01(17) . . . . ?
C18 C19 C20 O1 0.2(3) . . . . ?
C18 C19 C20 C21 179.93(16) . . . . ?
C19 C20 C21 C22 179.49(17) . . . . ?

_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_191012a_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2052431'
loop_
_audit_author_name
_audit_author_address
qianbaiyang
;AnHui Normal University
China
;
_audit_update_record             
;
2020-12-25 deposited with the CCDC.	2021-03-25 downloaded from the CCDC.
;
_audit_creation_date             2019-10-12
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H18 N2 O2'
_chemical_formula_sum            'C22 H18 N2 O2'
_chemical_formula_weight         342.38
_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      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                   7.752(2)
_cell_length_b                   10.496(3)
_cell_length_c                   11.381(3)
_cell_angle_alpha                93.456(3)
_cell_angle_beta                 101.918(3)
_cell_angle_gamma                103.845(3)
_cell_volume                     873.9(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2363
_cell_measurement_temperature    298.15
_cell_measurement_theta_max      27.378
_cell_measurement_theta_min      2.566
_shelx_estimated_absorpt_T_max   0.983
_shelx_estimated_absorpt_T_min   0.980
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6627
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.0873 before and 0.0376 after correction. The Ratio of minimum to maximum transmission is 0.8888. The λ/2 correction factor is 0.00150.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.301
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             360
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.21
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0212
_diffrn_reflns_av_unetI/netI     0.0385
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_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            7393
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.529
_diffrn_reflns_theta_min         1.841
_diffrn_ambient_temperature      298.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.976
_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                2483
_reflns_number_total             3924
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.422
_refine_diff_density_min         -0.182
_refine_diff_density_rms         0.042
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         3924
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0986
_refine_ls_R_factor_gt           0.0603
_refine_ls_restrained_S_all      1.026
_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)+(0.0817P)²+0.2966P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1573
_refine_ls_wR_factor_ref         0.1853
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Rigid bond restraints
 C16, C17, C18
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
3.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C7(H7), C9(H9), C10(H10), C15(H15), C16(H16),
 C17(H17), C20(H20), C21(H21), C22(H22)
3.b Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C13(H13A,H13B,H13C)
;
_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
O1 O 0.8608(2) 0.57335(17) 0.57855(15) 0.0708(5) Uani 1 1 d . . . . .
O2 O 0.7453(2) 0.35492(15) 0.55037(14) 0.0592(5) Uani 1 1 d . . . . .
N1 N 0.5604(2) 0.73134(17) 0.19915(16) 0.0499(5) Uani 1 1 d . . . . .
N2 N 0.8967(3) 0.8345(2) 0.14795(18) 0.0619(5) Uani 1 1 d . . . . .
C1 C 0.5286(3) 0.6044(2) 0.23691(18) 0.0431(5) Uani 1 1 d . . . . .
C2 C 0.3966(3) 0.5192(2) 0.1485(2) 0.0495(5) Uani 1 1 d . . . . .
C3 C 0.3457(3) 0.5946(2) 0.0515(2) 0.0481(5) Uani 1 1 d . . . . .
C4 C 0.2222(3) 0.5648(2) -0.0606(2) 0.0598(6) Uani 1 1 d . . . . .
H4 H 0.149577 0.479191 -0.085395 0.072 Uiso 1 1 calc R . . . .
C5 C 0.2087(3) 0.6627(3) -0.1342(2) 0.0637(7) Uani 1 1 d . . . . .
H5 H 0.125700 0.643397 -0.208670 0.076 Uiso 1 1 calc R . . . .
C6 C 0.3191(4) 0.7916(3) -0.0977(2) 0.0630(7) Uani 1 1 d . . . . .
H6 H 0.309510 0.856598 -0.148899 0.076 Uiso 1 1 calc R . . . .
C7 C 0.4411(3) 0.8233(2) 0.0122(2) 0.0586(6) Uani 1 1 d . . . . .
H7 H 0.514591 0.908628 0.036544 0.070 Uiso 1 1 calc R . . . .
C8 C 0.4507(3) 0.7240(2) 0.08514(19) 0.0471(5) Uani 1 1 d . . . . .
C9 C 0.6332(3) 0.5858(2) 0.35186(18) 0.0448(5) Uani 1 1 d . . . . .
H9 H 0.707969 0.662543 0.398607 0.054 Uiso 1 1 calc R . . . .
C10 C 0.6377(3) 0.4751(2) 0.4000(2) 0.0516(6) Uani 1 1 d . . . . .
H10 H 0.562892 0.395246 0.358937 0.062 Uiso 1 1 calc R . . . .
C11 C 0.7594(3) 0.4767(2) 0.51767(19) 0.0481(5) Uani 1 1 d . . . . .
C12 C 0.8638(3) 0.3442(3) 0.6624(2) 0.0655(7) Uani 1 1 d . . . . .
H12A H 0.987879 0.385369 0.660836 0.098 Uiso 1 1 calc GR . . . .
H12B H 0.851393 0.252675 0.673066 0.098 Uiso 1 1 calc GR . . . .
H12C H 0.831240 0.387428 0.728188 0.098 Uiso 1 1 calc GR . . . .
C13 C 0.3172(4) 0.3780(2) 0.1495(3) 0.0696(7) Uani 1 1 d . . . . .
H13A H 0.411933 0.332376 0.158127 0.104 Uiso 1 1 calc GR . . . .
H13B H 0.229077 0.343596 0.075014 0.104 Uiso 1 1 calc GR . . . .
H13C H 0.258674 0.365356 0.215989 0.104 Uiso 1 1 calc GR . . . .
C14 C 0.6785(3) 0.8508(2) 0.2649(2) 0.0500(5) Uani 1 1 d . . . . .
C15 C 0.6263(4) 0.9162(3) 0.3515(2) 0.0673(7) Uani 1 1 d . . . . .
H15 H 0.515373 0.879440 0.370673 0.081 Uiso 1 1 calc R . . . .
C16 C 0.7360(5) 1.0396(3) 0.4142(3) 0.0892(9) Uani 1 1 d . U . . .
H16 H 0.696040 1.083087 0.472758 0.107 Uiso 1 1 calc R . . . .
C17 C 0.8970(4) 1.0930(3) 0.3887(3) 0.0781(7) Uani 1 1 d . U . . .
H17 H 0.969055 1.173991 0.428946 0.094 Uiso 1 1 calc R . . . .
C18 C 0.9568(3) 1.0251(2) 0.3000(2) 0.0630(6) Uani 1 1 d . U . . .
C19 C 0.8466(3) 0.9029(2) 0.2367(2) 0.0515(6) Uani 1 1 d . . . . .
C20 C 1.1224(5) 1.0753(3) 0.2697(3) 0.0928(11) Uani 1 1 d . . . . .
H20 H 1.200022 1.154547 0.309844 0.111 Uiso 1 1 calc R . . . .
C21 C 1.1706(4) 1.0088(4) 0.1817(4) 0.1024(12) Uani 1 1 d . . . . .
H21 H 1.280647 1.042337 0.160237 0.123 Uiso 1 1 calc R . . . .
C22 C 1.0541(4) 0.8900(4) 0.1239(3) 0.0863(9) Uani 1 1 d . . . . .
H22 H 1.090232 0.846407 0.063456 0.104 Uiso 1 1 calc R . . . .


_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 C11 1.199(3) . ?
O2 C11 1.338(3) . ?
O2 C12 1.437(3) . ?
N1 C1 1.406(3) . ?
N1 C8 1.383(3) . ?
N1 C14 1.423(3) . ?
N2 C19 1.377(3) . ?
N2 C22 1.311(3) . ?
C1 C2 1.374(3) . ?
C1 C9 1.440(3) . ?
C2 C3 1.441(3) . ?
C2 C13 1.464(3) . ?
C3 C4 1.395(3) . ?
C3 C8 1.390(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.374(4) . ?
C5 H5 0.9300 . ?
C5 C6 1.402(3) . ?
C6 H6 0.9300 . ?
C6 C7 1.371(3) . ?
C7 H7 0.9300 . ?
C7 C8 1.377(3) . ?
C9 H9 0.9300 . ?
C9 C10 1.319(3) . ?
C10 H10 0.9300 . ?
C10 C11 1.467(3) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 C15 1.350(3) . ?
C14 C19 1.397(3) . ?
C15 H15 0.9300 . ?
C15 C16 1.422(4) . ?
C16 H16 0.9300 . ?
C16 C17 1.338(4) . ?
C17 H17 0.9300 . ?
C17 C18 1.417(4) . ?
C18 C19 1.415(3) . ?
C18 C20 1.388(4) . ?
C20 H20 0.9300 . ?
C20 C21 1.350(5) . ?
C21 H21 0.9300 . ?
C21 C22 1.385(5) . ?
C22 H22 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
C11 O2 C12 116.39(18) . . ?
C1 N1 C14 127.74(17) . . ?
C8 N1 C1 108.38(17) . . ?
C8 N1 C14 123.85(18) . . ?
C22 N2 C19 115.8(2) . . ?
N1 C1 C9 118.72(18) . . ?
C2 C1 N1 108.54(18) . . ?
C2 C1 C9 132.7(2) . . ?
C1 C2 C3 107.32(19) . . ?
C1 C2 C13 127.8(2) . . ?
C3 C2 C13 124.8(2) . . ?
C4 C3 C2 134.5(2) . . ?
C8 C3 C2 107.25(19) . . ?
C8 C3 C4 118.3(2) . . ?
C3 C4 H4 120.2 . . ?
C5 C4 C3 119.5(2) . . ?
C5 C4 H4 120.2 . . ?
C4 C5 H5 119.8 . . ?
C4 C5 C6 120.4(2) . . ?
C6 C5 H5 119.8 . . ?
C5 C6 H6 119.5 . . ?
C7 C6 C5 121.1(2) . . ?
C7 C6 H6 119.5 . . ?
C6 C7 H7 121.2 . . ?
C6 C7 C8 117.5(2) . . ?
C8 C7 H7 121.2 . . ?
N1 C8 C3 108.47(18) . . ?
C7 C8 N1 128.4(2) . . ?
C7 C8 C3 123.2(2) . . ?
C1 C9 H9 115.5 . . ?
C10 C9 C1 129.0(2) . . ?
C10 C9 H9 115.5 . . ?
C9 C10 H10 119.7 . . ?
C9 C10 C11 120.6(2) . . ?
C11 C10 H10 119.7 . . ?
O1 C11 O2 122.9(2) . . ?
O1 C11 C10 125.4(2) . . ?
O2 C11 C10 111.63(18) . . ?
O2 C12 H12A 109.5 . . ?
O2 C12 H12B 109.5 . . ?
O2 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C2 C13 H13A 109.5 . . ?
C2 C13 H13B 109.5 . . ?
C2 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C15 C14 N1 120.3(2) . . ?
C15 C14 C19 119.9(2) . . ?
C19 C14 N1 119.8(2) . . ?
C14 C15 H15 119.1 . . ?
C14 C15 C16 121.9(3) . . ?
C16 C15 H15 119.1 . . ?
C15 C16 H16 120.1 . . ?
C17 C16 C15 119.8(3) . . ?
C17 C16 H16 120.1 . . ?
C16 C17 H17 120.3 . . ?
C16 C17 C18 119.5(3) . . ?
C18 C17 H17 120.3 . . ?
C19 C18 C17 120.7(2) . . ?
C20 C18 C17 122.2(3) . . ?
C20 C18 C19 117.1(3) . . ?
N2 C19 C14 118.8(2) . . ?
N2 C19 C18 122.9(2) . . ?
C14 C19 C18 118.3(2) . . ?
C18 C20 H20 120.0 . . ?
C21 C20 C18 119.9(3) . . ?
C21 C20 H20 120.0 . . ?
C20 C21 H21 120.4 . . ?
C20 C21 C22 119.2(3) . . ?
C22 C21 H21 120.4 . . ?
N2 C22 C21 125.0(3) . . ?
N2 C22 H22 117.5 . . ?
C21 C22 H22 117.5 . . ?

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
N1 C1 C2 C3 0.8(2) . . . . ?
N1 C1 C2 C13 -178.6(2) . . . . ?
N1 C1 C9 C10 -173.5(2) . . . . ?
N1 C14 C15 C16 -176.3(2) . . . . ?
N1 C14 C19 N2 -2.2(3) . . . . ?
N1 C14 C19 C18 177.05(18) . . . . ?
C1 N1 C8 C3 1.7(2) . . . . ?
C1 N1 C8 C7 -177.8(2) . . . . ?
C1 N1 C14 C15 -78.7(3) . . . . ?
C1 N1 C14 C19 103.5(3) . . . . ?
C1 C2 C3 C4 179.8(2) . . . . ?
C1 C2 C3 C8 0.2(2) . . . . ?
C1 C9 C10 C11 177.8(2) . . . . ?
C2 C1 C9 C10 5.4(4) . . . . ?
C2 C3 C4 C5 -179.2(2) . . . . ?
C2 C3 C8 N1 -1.2(2) . . . . ?
C2 C3 C8 C7 178.4(2) . . . . ?
C3 C4 C5 C6 0.6(4) . . . . ?
C4 C3 C8 N1 179.11(19) . . . . ?
C4 C3 C8 C7 -1.3(3) . . . . ?
C4 C5 C6 C7 -0.8(4) . . . . ?
C5 C6 C7 C8 -0.1(4) . . . . ?
C6 C7 C8 N1 -179.4(2) . . . . ?
C6 C7 C8 C3 1.1(4) . . . . ?
C8 N1 C1 C2 -1.6(2) . . . . ?
C8 N1 C1 C9 177.57(18) . . . . ?
C8 N1 C14 C15 98.9(3) . . . . ?
C8 N1 C14 C19 -78.8(3) . . . . ?
C8 C3 C4 C5 0.4(3) . . . . ?
C9 C1 C2 C3 -178.2(2) . . . . ?
C9 C1 C2 C13 2.4(4) . . . . ?
C9 C10 C11 O1 0.2(4) . . . . ?
C9 C10 C11 O2 -179.4(2) . . . . ?
C12 O2 C11 O1 -1.9(3) . . . . ?
C12 O2 C11 C10 177.74(19) . . . . ?
C13 C2 C3 C4 -0.7(4) . . . . ?
C13 C2 C3 C8 179.7(2) . . . . ?
C14 N1 C1 C2 176.3(2) . . . . ?
C14 N1 C1 C9 -4.5(3) . . . . ?
C14 N1 C8 C3 -176.3(2) . . . . ?
C14 N1 C8 C7 4.1(4) . . . . ?
C14 C15 C16 C17 -0.8(5) . . . . ?
C15 C14 C19 N2 -179.9(2) . . . . ?
C15 C14 C19 C18 -0.7(3) . . . . ?
C15 C16 C17 C18 -0.5(5) . . . . ?
C16 C17 C18 C19 1.2(4) . . . . ?
C16 C17 C18 C20 -179.9(3) . . . . ?
C17 C18 C19 N2 178.6(2) . . . . ?
C17 C18 C19 C14 -0.6(3) . . . . ?
C17 C18 C20 C21 -177.9(3) . . . . ?
C18 C20 C21 C22 -0.8(5) . . . . ?
C19 N2 C22 C21 0.9(4) . . . . ?
C19 C14 C15 C16 1.4(4) . . . . ?
C19 C18 C20 C21 1.0(4) . . . . ?
C20 C18 C19 N2 -0.3(3) . . . . ?
C20 C18 C19 C14 -179.5(2) . . . . ?
C20 C21 C22 N2 -0.3(5) . . . . ?
C22 N2 C19 C14 178.6(2) . . . . ?
C22 N2 C19 C18 -0.6(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
