# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_shelxl
_database_code_depnum_ccdc_archive 'CCDC 1954587'
loop_
_audit_author_name
_audit_author_address
NB-one
;China Three Gorges University
China
;
_audit_update_record             
;
2019-09-19 deposited with the CCDC.	2019-10-21 downloaded from the CCDC.
;
_audit_creation_date             2018-12-25
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H22 N2 O2'
_chemical_formula_sum            'C23 H22 N2 O2'
_chemical_formula_weight         358.42
_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                   21.762(4)
_cell_length_b                   6.5576(13)
_cell_length_c                   27.605(6)
_cell_angle_alpha                90
_cell_angle_beta                 100.00(3)
_cell_angle_gamma                90
_cell_volume                     3879.5(14)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    4532
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      27.9183
_cell_measurement_theta_min      1.4981
_shelx_estimated_absorpt_T_max   0.991
_shelx_estimated_absorpt_T_min   0.984
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.7429
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   crystalclear
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.227
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             1520
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0585
_diffrn_reflns_av_unetI/netI     0.0471
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_number            21928
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.901
_diffrn_reflns_theta_min         2.206
_diffrn_ambient_temperature      113.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Rigaku Saturn 70 CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  confocal
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3736
_reflns_number_total             4618
_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       crystalclear
_computing_data_collection       crystalclear
_computing_data_reduction        crystalclear
_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    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.269
_refine_diff_density_min         -0.233
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       0.0061(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.098
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     252
_refine_ls_number_reflns         4618
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0728
_refine_ls_R_factor_gt           0.0578
_refine_ls_restrained_S_all      1.098
_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)+(0.0625P)²+0.9771P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1331
_refine_ls_wR_factor_ref         0.1429
_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:
 C22(H22A,H22B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C8(H8), C9(H9), C15(H15), C16(H16), C19(H19),
 C20(H20)
2.c Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C13(H13A,H13B,H13C), C23(H23A,H23B,H23C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_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 0.36844(5) 0.97970(19) 0.03014(5) 0.0467(3) Uani 1 1 d . . . . .
O2 O 0.46703(5) 1.04202(17) 0.06692(4) 0.0413(3) Uani 1 1 d . . . . .
N1 N 0.30417(6) 0.22806(19) 0.13952(4) 0.0300(3) Uani 1 1 d . . . . .
N2 N 0.39743(6) 0.4914(2) 0.13719(5) 0.0346(3) Uani 1 1 d . . . . .
C1 C 0.28271(7) 0.0443(2) 0.15768(5) 0.0287(3) Uani 1 1 d . . . . .
C2 C 0.31705(7) -0.0780(2) 0.19523(5) 0.0313(3) Uani 1 1 d . . . . .
C3 C 0.37790(8) -0.0311(3) 0.22005(6) 0.0426(4) Uani 1 1 d . . . . .
H3 H 0.397959 0.090004 0.212117 0.051 Uiso 1 1 calc R . . . .
C4 C 0.40794(8) -0.1599(3) 0.25548(7) 0.0516(5) Uani 1 1 d . . . . .
H4 H 0.448832 -0.127483 0.271909 0.062 Uiso 1 1 calc R . . . .
C5 C 0.37899(9) -0.3390(3) 0.26777(7) 0.0482(5) Uani 1 1 d . . . . .
H5 H 0.400332 -0.426672 0.292501 0.058 Uiso 1 1 calc R . . . .
C6 C 0.32042(8) -0.3880(3) 0.24444(6) 0.0414(4) Uani 1 1 d . . . . .
H6 H 0.301573 -0.510507 0.252981 0.050 Uiso 1 1 calc R . . . .
C7 C 0.28708(7) -0.2595(2) 0.20763(5) 0.0321(3) Uani 1 1 d . . . . .
C8 C 0.22596(8) -0.3068(2) 0.18331(5) 0.0344(4) Uani 1 1 d . . . . .
H8 H 0.206302 -0.426999 0.192273 0.041 Uiso 1 1 calc R . . . .
C9 C 0.19433(8) -0.1834(2) 0.14710(5) 0.0331(3) Uani 1 1 d . . . . .
H9 H 0.153398 -0.217872 0.131129 0.040 Uiso 1 1 calc R . . . .
C10 C 0.22347(7) -0.0060(2) 0.13415(5) 0.0286(3) Uani 1 1 d . . . . .
C11 C 0.20286(7) 0.1544(2) 0.09566(5) 0.0291(3) Uani 1 1 d . . . . .
C12 C 0.14327(7) 0.2656(2) 0.10301(6) 0.0353(4) Uani 1 1 d . . . . .
H12A H 0.108123 0.169968 0.097778 0.053 Uiso 1 1 calc GR . . . .
H12B H 0.134922 0.377970 0.079390 0.053 Uiso 1 1 calc GR . . . .
H12C H 0.148629 0.319835 0.136555 0.053 Uiso 1 1 calc GR . . . .
C13 C 0.19519(8) 0.0660(3) 0.04311(5) 0.0357(4) Uani 1 1 d . . . . .
H13A H 0.235028 0.008682 0.037692 0.054 Uiso 1 1 calc GR . . . .
H13B H 0.182282 0.174691 0.019127 0.054 Uiso 1 1 calc GR . . . .
H13C H 0.163400 -0.041370 0.039162 0.054 Uiso 1 1 calc GR . . . .
C14 C 0.26008(7) 0.2943(2) 0.10468(5) 0.0280(3) Uani 1 1 d . . . . .
C15 C 0.26286(7) 0.4747(2) 0.07530(6) 0.0314(3) Uani 1 1 d . . . . .
H15 H 0.225342 0.504155 0.053230 0.038 Uiso 1 1 calc R . . . .
C16 C 0.30975(7) 0.6099(2) 0.07366(5) 0.0303(3) Uani 1 1 d . . . . .
H16 H 0.299145 0.716284 0.050352 0.036 Uiso 1 1 calc R . . . .
C17 C 0.37231(7) 0.6220(2) 0.10055(5) 0.0285(3) Uani 1 1 d . . . . .
C18 C 0.41893(7) 0.7643(2) 0.09537(5) 0.0308(3) Uani 1 1 d . . . . .
C19 C 0.47225(7) 0.7129(3) 0.13005(6) 0.0403(4) Uani 1 1 d . . . . .
H19 H 0.511190 0.782122 0.135116 0.048 Uiso 1 1 calc R . . . .
C20 C 0.45746(8) 0.5452(3) 0.15498(6) 0.0448(4) Uani 1 1 d . . . . .
H20 H 0.484647 0.477228 0.180563 0.054 Uiso 1 1 calc R . . . .
C21 C 0.41342(7) 0.9351(2) 0.06088(6) 0.0333(4) Uani 1 1 d . . . . .
C22 C 0.46837(8) 1.2192(3) 0.03600(7) 0.0446(4) Uani 1 1 d . . . . .
H22A H 0.437527 1.321775 0.042691 0.053 Uiso 1 1 calc R . . . .
H22B H 0.458764 1.180754 0.000817 0.053 Uiso 1 1 calc R . . . .
C23 C 0.53371(9) 1.3027(3) 0.04879(8) 0.0536(5) Uani 1 1 d . . . . .
H23A H 0.542592 1.337987 0.083803 0.080 Uiso 1 1 calc GR . . . .
H23B H 0.537482 1.424840 0.029072 0.080 Uiso 1 1 calc GR . . . .
H23C H 0.563544 1.199423 0.041806 0.080 Uiso 1 1 calc GR . . . .
H2 H 0.3726(10) 0.386(3) 0.1459(7) 0.062(6) 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 C21 1.2147(18) . ?
O2 C21 1.3466(18) . ?
O2 C22 1.4450(19) . ?
N1 C1 1.4152(19) . ?
N1 C14 1.3090(18) . ?
N2 C17 1.3652(19) . ?
N2 C20 1.360(2) . ?
N2 H2 0.94(2) . ?
C1 C2 1.417(2) . ?
C1 C10 1.379(2) . ?
C2 C3 1.415(2) . ?
C2 C7 1.427(2) . ?
C3 H3 0.9500 . ?
C3 C4 1.369(2) . ?
C4 H4 0.9500 . ?
C4 C5 1.402(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.363(3) . ?
C6 H6 0.9500 . ?
C6 C7 1.419(2) . ?
C7 C8 1.416(2) . ?
C8 H8 0.9500 . ?
C8 C9 1.374(2) . ?
C9 H9 0.9500 . ?
C9 C10 1.401(2) . ?
C10 C11 1.507(2) . ?
C11 C12 1.531(2) . ?
C11 C13 1.544(2) . ?
C11 C14 1.532(2) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 C15 1.442(2) . ?
C15 H15 0.9500 . ?
C15 C16 1.358(2) . ?
C16 H16 0.9500 . ?
C16 C17 1.435(2) . ?
C17 C18 1.404(2) . ?
C18 C19 1.411(2) . ?
C18 C21 1.461(2) . ?
C19 H19 0.9500 . ?
C19 C20 1.365(2) . ?
C20 H20 0.9500 . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C22 C23 1.507(2) . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C21 O2 C22 116.85(12) . . ?
C14 N1 C1 107.32(12) . . ?
C17 N2 H2 118.8(13) . . ?
C20 N2 C17 109.91(13) . . ?
C20 N2 H2 131.3(13) . . ?
N1 C1 C2 125.22(13) . . ?
C10 C1 N1 112.07(13) . . ?
C10 C1 C2 122.70(14) . . ?
C1 C2 C7 116.29(14) . . ?
C3 C2 C1 124.16(14) . . ?
C3 C2 C7 119.55(14) . . ?
C2 C3 H3 119.9 . . ?
C4 C3 C2 120.17(16) . . ?
C4 C3 H3 119.9 . . ?
C3 C4 H4 119.6 . . ?
C3 C4 C5 120.70(17) . . ?
C5 C4 H4 119.6 . . ?
C4 C5 H5 119.8 . . ?
C6 C5 C4 120.40(16) . . ?
C6 C5 H5 119.8 . . ?
C5 C6 H6 119.4 . . ?
C5 C6 C7 121.20(16) . . ?
C7 C6 H6 119.4 . . ?
C6 C7 C2 117.98(15) . . ?
C8 C7 C2 119.96(14) . . ?
C8 C7 C6 122.06(15) . . ?
C7 C8 H8 119.1 . . ?
C9 C8 C7 121.77(14) . . ?
C9 C8 H8 119.1 . . ?
C8 C9 H9 120.6 . . ?
C8 C9 C10 118.86(14) . . ?
C10 C9 H9 120.6 . . ?
C1 C10 C9 120.40(14) . . ?
C1 C10 C11 107.73(13) . . ?
C9 C10 C11 131.85(14) . . ?
C10 C11 C12 113.22(13) . . ?
C10 C11 C13 111.75(12) . . ?
C10 C11 C14 99.75(11) . . ?
C12 C11 C13 110.31(13) . . ?
C12 C11 C14 112.14(12) . . ?
C14 C11 C13 109.25(12) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C11 C13 H13A 109.5 . . ?
C11 C13 H13B 109.5 . . ?
C11 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N1 C14 C11 113.11(13) . . ?
N1 C14 C15 126.05(13) . . ?
C15 C14 C11 120.81(13) . . ?
C14 C15 H15 114.4 . . ?
C16 C15 C14 131.27(14) . . ?
C16 C15 H15 114.4 . . ?
C15 C16 H16 114.0 . . ?
C15 C16 C17 132.02(14) . . ?
C17 C16 H16 114.0 . . ?
N2 C17 C16 124.76(13) . . ?
N2 C17 C18 106.81(13) . . ?
C18 C17 C16 128.43(14) . . ?
C17 C18 C19 107.21(13) . . ?
C17 C18 C21 126.64(14) . . ?
C19 C18 C21 126.15(14) . . ?
C18 C19 H19 126.4 . . ?
C20 C19 C18 107.24(14) . . ?
C20 C19 H19 126.4 . . ?
N2 C20 C19 108.84(14) . . ?
N2 C20 H20 125.6 . . ?
C19 C20 H20 125.6 . . ?
O1 C21 O2 122.46(14) . . ?
O1 C21 C18 127.22(14) . . ?
O2 C21 C18 110.32(13) . . ?
O2 C22 H22A 110.6 . . ?
O2 C22 H22B 110.6 . . ?
O2 C22 C23 105.58(13) . . ?
H22A C22 H22B 108.8 . . ?
C23 C22 H22A 110.6 . . ?
C23 C22 H22B 110.6 . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C16 H16 O1 0.95 2.42 3.0804(19) 126.3 . yes

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C2 C3 0.5(2) . . . . ?
N1 C1 C2 C7 -179.11(13) . . . . ?
N1 C1 C10 C9 179.92(13) . . . . ?
N1 C1 C10 C11 1.35(17) . . . . ?
N1 C14 C15 C16 4.1(3) . . . . ?
N2 C17 C18 C19 0.10(17) . . . . ?
N2 C17 C18 C21 -179.42(15) . . . . ?
C1 N1 C14 C11 -0.44(17) . . . . ?
C1 N1 C14 C15 -178.39(14) . . . . ?
C1 C2 C3 C4 -179.12(16) . . . . ?
C1 C2 C7 C6 178.86(13) . . . . ?
C1 C2 C7 C8 -1.0(2) . . . . ?
C1 C10 C11 C12 -120.75(14) . . . . ?
C1 C10 C11 C13 113.95(14) . . . . ?
C1 C10 C11 C14 -1.43(15) . . . . ?
C2 C1 C10 C9 0.4(2) . . . . ?
C2 C1 C10 C11 -178.13(13) . . . . ?
C2 C3 C4 C5 -0.2(3) . . . . ?
C2 C7 C8 C9 0.9(2) . . . . ?
C3 C2 C7 C6 -0.8(2) . . . . ?
C3 C2 C7 C8 179.42(14) . . . . ?
C3 C4 C5 C6 0.2(3) . . . . ?
C4 C5 C6 C7 -0.5(3) . . . . ?
C5 C6 C7 C2 0.8(2) . . . . ?
C5 C6 C7 C8 -179.38(16) . . . . ?
C6 C7 C8 C9 -178.87(14) . . . . ?
C7 C2 C3 C4 0.5(3) . . . . ?
C7 C8 C9 C10 -0.2(2) . . . . ?
C8 C9 C10 C1 -0.5(2) . . . . ?
C8 C9 C10 C11 177.68(15) . . . . ?
C9 C10 C11 C12 60.9(2) . . . . ?
C9 C10 C11 C13 -64.4(2) . . . . ?
C9 C10 C11 C14 -179.77(15) . . . . ?
C10 C1 C2 C3 179.89(15) . . . . ?
C10 C1 C2 C7 0.3(2) . . . . ?
C10 C11 C14 N1 1.16(16) . . . . ?
C10 C11 C14 C15 179.23(13) . . . . ?
C11 C14 C15 C16 -173.73(15) . . . . ?
C12 C11 C14 N1 121.27(14) . . . . ?
C12 C11 C14 C15 -60.65(18) . . . . ?
C13 C11 C14 N1 -116.11(14) . . . . ?
C13 C11 C14 C15 61.96(18) . . . . ?
C14 N1 C1 C2 178.88(14) . . . . ?
C14 N1 C1 C10 -0.59(17) . . . . ?
C14 C15 C16 C17 -0.6(3) . . . . ?
C15 C16 C17 N2 -2.6(3) . . . . ?
C15 C16 C17 C18 177.58(16) . . . . ?
C16 C17 C18 C19 179.93(15) . . . . ?
C16 C17 C18 C21 0.4(3) . . . . ?
C17 N2 C20 C19 0.1(2) . . . . ?
C17 C18 C19 C20 0.0(2) . . . . ?
C17 C18 C21 O1 -2.1(3) . . . . ?
C17 C18 C21 O2 178.69(14) . . . . ?
C18 C19 C20 N2 -0.1(2) . . . . ?
C19 C18 C21 O1 178.49(17) . . . . ?
C19 C18 C21 O2 -0.7(2) . . . . ?
C20 N2 C17 C16 -179.98(15) . . . . ?
C20 N2 C17 C18 -0.14(18) . . . . ?
C21 O2 C22 C23 -177.58(15) . . . . ?
C21 C18 C19 C20 179.49(16) . . . . ?
C22 O2 C21 O1 2.0(2) . . . . ?
C22 O2 C21 C18 -178.69(14) . . . . ?

_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_shelxl_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1954588'
loop_
_audit_author_name
_audit_author_address
NB-three
;China Three Gorges University
China
;
_audit_update_record             
;
2019-09-19 deposited with the CCDC.	2019-10-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H22 N2 O2'
_chemical_formula_weight         358.42

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'

_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                   9.6810(19)
_cell_length_b                   11.462(2)
_cell_length_c                   16.848(3)
_cell_angle_alpha                90
_cell_angle_beta                 98.17(3)
_cell_angle_gamma                90
_cell_volume                     1850.5(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    113(2)
_cell_measurement_reflns_used    3930
_cell_measurement_theta_min      2.1560
_cell_measurement_theta_max      28.0915

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.286
_exptl_crystal_F_000             760
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.083
_shelx_estimated_absorpt_T_min   0.984
_shelx_estimated_absorpt_T_max   0.990
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.7457
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_process_details   crystalclear
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      113(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'rigaku saturn'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            19376
_diffrn_reflns_av_unetI/netI     0.0939
_diffrn_reflns_av_R_equivalents  0.0758
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.156
_diffrn_reflns_theta_max         27.903
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             4389
_reflns_number_gt                2214
_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       crystalclear
_computing_cell_refinement       crystalclear
_computing_data_reduction        crystalclear
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4389
_refine_ls_number_parameters     250
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0996
_refine_ls_R_factor_gt           0.0493
_refine_ls_wR_factor_ref         0.1181
_refine_ls_wR_factor_gt          0.0963
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_restrained_S_all      1.012
_refine_ls_shift/su_max          0.000
_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
O1 O 0.16119(17) 0.64128(12) -0.18282(8) 0.0434(4) Uani 1 1 d . . . . .
O2 O 0.28500(15) 0.52324(12) -0.09198(8) 0.0391(4) Uani 1 1 d . . . . .
N1 N 0.09583(16) 0.60672(13) 0.22477(9) 0.0229(4) Uani 1 1 d . . . . .
N2 N 0.03456(17) 0.67139(14) 0.06868(9) 0.0259(4) Uani 1 1 d D . . . .
H2 H 0.032(2) 0.6636(15) 0.1224(6) 0.031 Uiso 1 1 d D U . . .
C1 C 0.08683(19) 0.62425(15) 0.30766(11) 0.0215(4) Uani 1 1 d . . . . .
C2 C 0.0069(2) 0.71192(15) 0.33827(11) 0.0252(4) Uani 1 1 d . . . . .
H2A H -0.048989 0.764009 0.303472 0.030 Uiso 1 1 calc R U . . .
C3 C 0.0123(2) 0.71952(16) 0.41967(12) 0.0270(5) Uani 1 1 d . . . . .
H3 H -0.039583 0.778822 0.441492 0.032 Uiso 1 1 calc R U . . .
C4 C 0.09355(19) 0.64118(15) 0.47242(11) 0.0232(4) Uani 1 1 d . . . . .
C5 C 0.0968(2) 0.64939(16) 0.55645(11) 0.0285(5) Uani 1 1 d . . . . .
H5 H 0.045095 0.709132 0.577960 0.034 Uiso 1 1 calc R U . . .
C6 C 0.1733(2) 0.57266(16) 0.60732(12) 0.0312(5) Uani 1 1 d . . . . .
H6 H 0.175031 0.579841 0.663626 0.037 Uiso 1 1 calc R U . . .
C7 C 0.2496(2) 0.48284(17) 0.57600(12) 0.0299(5) Uani 1 1 d . . . . .
H7 H 0.301533 0.429268 0.611503 0.036 Uiso 1 1 calc R U . . .
C8 C 0.24949(19) 0.47212(16) 0.49530(11) 0.0262(5) Uani 1 1 d . . . . .
H8 H 0.301622 0.411142 0.475492 0.031 Uiso 1 1 calc R U . . .
C9 C 0.17279(19) 0.55055(15) 0.44039(11) 0.0223(4) Uani 1 1 d . . . . .
C10 C 0.16743(19) 0.54586(15) 0.35615(11) 0.0218(4) Uani 1 1 d . . . . .
C11 C 0.23615(19) 0.46490(15) 0.30204(11) 0.0233(4) Uani 1 1 d . . . . .
C12 C 0.1802(2) 0.33879(15) 0.30375(12) 0.0301(5) Uani 1 1 d . . . . .
H12A H 0.205680 0.305991 0.357560 0.045 Uiso 1 1 calc R U . . .
H12B H 0.221076 0.291099 0.264779 0.045 Uiso 1 1 calc R U . . .
H12C H 0.078387 0.339307 0.290003 0.045 Uiso 1 1 calc R U . . .
C13 C 0.3969(2) 0.46832(17) 0.31840(12) 0.0318(5) Uani 1 1 d . . . . .
H13A H 0.429357 0.547599 0.309451 0.048 Uiso 1 1 calc R U . . .
H13B H 0.435143 0.414200 0.282085 0.048 Uiso 1 1 calc R U . . .
H13C H 0.428465 0.445348 0.374055 0.048 Uiso 1 1 calc R U . . .
C14 C 0.18293(19) 0.51907(15) 0.22063(11) 0.0235(4) Uani 1 1 d . . . . .
C15 C 0.2313(2) 0.47607(16) 0.14850(11) 0.0264(5) Uani 1 1 d . . . . .
H15 H 0.288366 0.408504 0.156809 0.032 Uiso 1 1 calc R U . . .
C16 C 0.2108(2) 0.51375(15) 0.07151(12) 0.0258(4) Uani 1 1 d . . . . .
H16 H 0.261835 0.471114 0.037009 0.031 Uiso 1 1 calc R U . . .
C17 C 0.1264(2) 0.60613(16) 0.03181(11) 0.0239(4) Uani 1 1 d . . . . .
C18 C 0.1117(2) 0.64377(15) -0.04856(11) 0.0256(4) Uani 1 1 d . . . . .
C19 C 0.0085(2) 0.73136(16) -0.05764(12) 0.0311(5) Uani 1 1 d . . . . .
H19 H -0.023955 0.772488 -0.105630 0.037 Uiso 1 1 calc R U . . .
C20 C -0.0368(2) 0.74665(16) 0.01532(12) 0.0298(5) Uani 1 1 d . . . . .
H20 H -0.106033 0.800491 0.026601 0.036 Uiso 1 1 calc R U . . .
C21 C 0.1843(2) 0.60355(17) -0.11475(13) 0.0316(5) Uani 1 1 d . . . . .
C22 C 0.3623(2) 0.47601(19) -0.15367(13) 0.0414(6) Uani 1 1 d . . . . .
H22A H 0.453357 0.445068 -0.128117 0.050 Uiso 1 1 calc R U . . .
H22B H 0.380315 0.538940 -0.191121 0.050 Uiso 1 1 calc R U . . .
C23 C 0.2810(2) 0.38171(18) -0.19847(13) 0.0439(6) Uani 1 1 d . . . . .
H23A H 0.254405 0.323769 -0.160646 0.066 Uiso 1 1 calc R U . . .
H23B H 0.338012 0.344254 -0.234852 0.066 Uiso 1 1 calc R U . . .
H23C H 0.196830 0.414633 -0.229604 0.066 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C21 1.216(2) . ?
O2 C21 1.356(2) . ?
O2 C22 1.468(2) . ?
N1 C14 1.320(2) . ?
N1 C1 1.426(2) . ?
N2 C20 1.361(2) . ?
N2 C17 1.375(2) . ?
N2 H2 0.912(9) . ?
C1 C10 1.379(2) . ?
C1 C2 1.410(2) . ?
C2 C3 1.368(3) . ?
C2 H2A 0.9500 . ?
C3 C4 1.420(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.415(3) . ?
C4 C9 1.441(2) . ?
C5 C6 1.370(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.412(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.365(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.421(2) . ?
C8 H8 0.9500 . ?
C9 C10 1.414(3) . ?
C10 C11 1.519(2) . ?
C11 C14 1.527(3) . ?
C11 C13 1.542(3) . ?
C11 C12 1.545(2) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 C15 1.450(2) . ?
C15 C16 1.355(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.443(2) . ?
C16 H16 0.9500 . ?
C17 C18 1.409(3) . ?
C18 C19 1.409(3) . ?
C18 C21 1.474(3) . ?
C19 C20 1.374(3) . ?
C19 H19 0.9500 . ?
C20 H20 0.9500 . ?
C22 C23 1.479(3) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C21 O2 C22 117.93(16) . . ?
C14 N1 C1 106.71(15) . . ?
C20 N2 C17 110.26(17) . . ?
C20 N2 H2 129.5(12) . . ?
C17 N2 H2 120.1(12) . . ?
C10 C1 C2 122.78(17) . . ?
C10 C1 N1 112.34(16) . . ?
C2 C1 N1 124.88(17) . . ?
C3 C2 C1 117.85(18) . . ?
C3 C2 H2A 121.1 . . ?
C1 C2 H2A 121.1 . . ?
C2 C3 C4 121.77(17) . . ?
C2 C3 H3 119.1 . . ?
C4 C3 H3 119.1 . . ?
C5 C4 C3 121.06(17) . . ?
C5 C4 C9 119.04(17) . . ?
C3 C4 C9 119.89(17) . . ?
C6 C5 C4 121.10(18) . . ?
C6 C5 H5 119.4 . . ?
C4 C5 H5 119.4 . . ?
C5 C6 C7 119.95(19) . . ?
C5 C6 H6 120.0 . . ?
C7 C6 H6 120.0 . . ?
C8 C7 C6 120.77(19) . . ?
C8 C7 H7 119.6 . . ?
C6 C7 H7 119.6 . . ?
C7 C8 C9 121.17(18) . . ?
C7 C8 H8 119.4 . . ?
C9 C8 H8 119.4 . . ?
C10 C9 C8 124.79(17) . . ?
C10 C9 C4 117.25(17) . . ?
C8 C9 C4 117.96(17) . . ?
C1 C10 C9 120.45(17) . . ?
C1 C10 C11 107.56(16) . . ?
C9 C10 C11 131.99(17) . . ?
C10 C11 C14 99.79(14) . . ?
C10 C11 C13 113.22(16) . . ?
C14 C11 C13 110.69(15) . . ?
C10 C11 C12 112.07(15) . . ?
C14 C11 C12 108.83(15) . . ?
C13 C11 C12 111.59(15) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C11 C13 H13A 109.5 . . ?
C11 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C11 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N1 C14 C15 126.03(17) . . ?
N1 C14 C11 113.49(16) . . ?
C15 C14 C11 120.46(16) . . ?
C16 C15 C14 132.34(18) . . ?
C16 C15 H15 113.8 . . ?
C14 C15 H15 113.8 . . ?
C15 C16 C17 132.39(18) . . ?
C15 C16 H16 113.8 . . ?
C17 C16 H16 113.8 . . ?
N2 C17 C18 106.51(17) . . ?
N2 C17 C16 123.35(17) . . ?
C18 C17 C16 130.04(18) . . ?
C17 C18 C19 107.18(17) . . ?
C17 C18 C21 129.61(18) . . ?
C19 C18 C21 123.21(18) . . ?
C20 C19 C18 107.78(18) . . ?
C20 C19 H19 126.1 . . ?
C18 C19 H19 126.1 . . ?
N2 C20 C19 108.27(17) . . ?
N2 C20 H20 125.9 . . ?
C19 C20 H20 125.9 . . ?
O1 C21 O2 122.47(19) . . ?
O1 C21 C18 123.9(2) . . ?
O2 C21 C18 113.53(17) . . ?
O2 C22 C23 110.06(18) . . ?
O2 C22 H22A 109.6 . . ?
C23 C22 H22A 109.6 . . ?
O2 C22 H22B 109.6 . . ?
C23 C22 H22B 109.6 . . ?
H22A C22 H22B 108.2 . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 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
C14 N1 C1 C10 -0.9(2) . . . . ?
C14 N1 C1 C2 178.37(17) . . . . ?
C10 C1 C2 C3 1.1(3) . . . . ?
N1 C1 C2 C3 -178.13(17) . . . . ?
C1 C2 C3 C4 -1.0(3) . . . . ?
C2 C3 C4 C5 -179.26(18) . . . . ?
C2 C3 C4 C9 -0.1(3) . . . . ?
C3 C4 C5 C6 178.91(18) . . . . ?
C9 C4 C5 C6 -0.2(3) . . . . ?
C4 C5 C6 C7 -0.6(3) . . . . ?
C5 C6 C7 C8 0.8(3) . . . . ?
C6 C7 C8 C9 -0.1(3) . . . . ?
C7 C8 C9 C10 179.80(18) . . . . ?
C7 C8 C9 C4 -0.7(3) . . . . ?
C5 C4 C9 C10 -179.59(17) . . . . ?
C3 C4 C9 C10 1.2(2) . . . . ?
C5 C4 C9 C8 0.9(3) . . . . ?
C3 C4 C9 C8 -178.29(16) . . . . ?
C2 C1 C10 C9 0.1(3) . . . . ?
N1 C1 C10 C9 179.37(16) . . . . ?
C2 C1 C10 C11 179.40(16) . . . . ?
N1 C1 C10 C11 -1.3(2) . . . . ?
C8 C9 C10 C1 178.26(18) . . . . ?
C4 C9 C10 C1 -1.2(3) . . . . ?
C8 C9 C10 C11 -0.8(3) . . . . ?
C4 C9 C10 C11 179.67(18) . . . . ?
C1 C10 C11 C14 2.64(19) . . . . ?
C9 C10 C11 C14 -178.17(19) . . . . ?
C1 C10 C11 C13 120.29(17) . . . . ?
C9 C10 C11 C13 -60.5(3) . . . . ?
C1 C10 C11 C12 -112.41(17) . . . . ?
C9 C10 C11 C12 66.8(3) . . . . ?
C1 N1 C14 C15 -175.36(17) . . . . ?
C1 N1 C14 C11 2.8(2) . . . . ?
C10 C11 C14 N1 -3.4(2) . . . . ?
C13 C11 C14 N1 -122.94(17) . . . . ?
C12 C11 C14 N1 114.08(17) . . . . ?
C10 C11 C14 C15 174.85(16) . . . . ?
C13 C11 C14 C15 55.3(2) . . . . ?
C12 C11 C14 C15 -67.7(2) . . . . ?
N1 C14 C15 C16 4.4(3) . . . . ?
C11 C14 C15 C16 -173.58(19) . . . . ?
C14 C15 C16 C17 -4.5(4) . . . . ?
C20 N2 C17 C18 0.5(2) . . . . ?
C20 N2 C17 C16 -176.09(17) . . . . ?
C15 C16 C17 N2 -6.2(3) . . . . ?
C15 C16 C17 C18 178.1(2) . . . . ?
N2 C17 C18 C19 -0.6(2) . . . . ?
C16 C17 C18 C19 175.68(18) . . . . ?
N2 C17 C18 C21 -179.89(17) . . . . ?
C16 C17 C18 C21 -3.6(3) . . . . ?
C17 C18 C19 C20 0.5(2) . . . . ?
C21 C18 C19 C20 179.85(17) . . . . ?
C17 N2 C20 C19 -0.2(2) . . . . ?
C18 C19 C20 N2 -0.2(2) . . . . ?
C22 O2 C21 O1 -3.7(3) . . . . ?
C22 O2 C21 C18 179.06(16) . . . . ?
C17 C18 C21 O1 178.6(2) . . . . ?
C19 C18 C21 O1 -0.6(3) . . . . ?
C17 C18 C21 O2 -4.2(3) . . . . ?
C19 C18 C21 O2 176.60(17) . . . . ?
C21 O2 C22 C23 -81.8(2) . . . . ?

_refine_diff_density_max         0.502
_refine_diff_density_min         -0.303
_refine_diff_density_rms         0.060

