# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2022

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

data_1
_database_code_depnum_ccdc_archive 'CCDC 2183433'
loop_
_audit_author_name
_audit_author_address
'Jiaqing Xu'
;China Agricultural University
China
;
_audit_update_record             
;
2022-07-01 deposited with the CCDC.	2022-09-05 downloaded from the CCDC.
;
_audit_creation_date             2022-05-05
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.08.20 svn.r13c46975 for OlexSys, GUI svn.r6396)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H26 N2 O3'
_chemical_formula_sum            'C18 H26 N2 O3'
_chemical_formula_weight         318.41
_chemical_absolute_configuration ad
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   6.9618(3)
_cell_length_b                   14.6189(6)
_cell_length_c                   18.3457(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1867.11(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8295
_cell_measurement_temperature    298.00
_cell_measurement_theta_max      61.687
_cell_measurement_theta_min      3.363
_shelx_estimated_absorpt_T_max   0.999
_shelx_estimated_absorpt_T_min   0.985
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_T_max  0.7526
_exptl_absorpt_correction_T_min  0.6094
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1613 before and 0.0677 after correction.
The Ratio of minimum to maximum transmission is 0.8097.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.133
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             688
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.01
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0524
_diffrn_reflns_av_unetI/netI     0.0433
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            17434
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.474
_diffrn_reflns_theta_min         1.781
_diffrn_ambient_temperature      298.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.985
_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_source_current           2.86
_diffrn_source_power             0.1997996
_diffrn_source_voltage           69.86
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.720
_reflns_Friedel_fraction_full    0.993
_reflns_Friedel_fraction_max     0.954
_reflns_number_gt                3432
_reflns_number_total             4150
_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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2018)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.676
_refine_diff_density_min         -0.603
_refine_diff_density_rms         0.071
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   -1(4)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.101
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     214
_refine_ls_number_reflns         4150
_refine_ls_number_restraints     156
_refine_ls_R_factor_all          0.1082
_refine_ls_R_factor_gt           0.0954
_refine_ls_restrained_S_all      1.180
_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)+(0.1793P)²+1.0249P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2786
_refine_ls_wR_factor_ref         0.2936
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 2(4)
 -1(4)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
3. Uiso/Uaniso restraints and constraints
C18 \\sim C16 \\sim C17 \\sim C15 \\sim N2 \\sim N1: within 2A with sigma of
0.01 and sigma for terminal atoms of 0.02 within 2A
C12 \\sim O2 \\sim O3 \\sim C13 \\sim C14: within 2A with sigma of 0.01 and
sigma for terminal atoms of 0.02 within 2A
Uanis(C18) \\sim Ueq, Uanis(C16) \\sim Ueq: with sigma of 0.005 and sigma for
terminal atoms of 0.01
Uanis(C13) \\sim Ueq, Uanis(C14) \\sim Ueq, Uanis(O3) \\sim Ueq, Uanis(O2)
\\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.01
Uanis(C18) \\sim Ueq, Uanis(C16) \\sim Ueq, Uanis(O3) \\sim Ueq, Uanis(C13)
\\sim Ueq, Uanis(C14) \\sim Ueq: with sigma of 0.001 and sigma for terminal
atoms of 0.002
4. Rigid body (RIGU) restrains
 C18, C17, C15, C16, N2, N1
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
 C12, C11, O2, O3, C13, C14
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
5.a Ternary CH refined with riding coordinates:
 C7(H7)
5.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C13(H13A,H13B)
5.c Aromatic/amide H refined with riding coordinates:
 N2(H2), C1(H1A), C5(H5), C3(H3), C2(H2A), C4(H4)
5.d X=CH2 refined with riding coordinates:
 C9(H9A,H9B)
5.e Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C18(H18A,H18B,H18C), C16(H16A,H16B,H16C), C14(H14A,H14B,
 H14C)
5.f Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_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 0.5219(5) 0.3450(2) 0.7042(3) 0.0558(10) Uani 1 1 d . . . . .
H1 H 0.573892 0.294786 0.700995 0.084 Uiso 1 1 calc R U . . .
O2 O 0.2699(7) 0.6884(3) 0.8060(3) 0.0694(13) Uani 1 1 d . U . . .
N1 N 0.1810(6) 0.4577(3) 0.8427(3) 0.0469(10) Uani 1 1 d . U . . .
N2 N 0.2240(7) 0.3747(3) 0.8195(3) 0.0538(11) Uani 1 1 d . U . . .
H2 H 0.280522 0.366752 0.778323 0.065 Uiso 1 1 calc R U . . .
O3 O 0.0878(8) 0.6216(3) 0.8922(3) 0.0738(12) Uani 1 1 d . U . . .
C10 C 0.3771(6) 0.5203(3) 0.7414(3) 0.0395(10) Uani 1 1 d . . . . .
H10A H 0.384114 0.579656 0.717887 0.047 Uiso 1 1 calc R U . . .
H10B H 0.320951 0.477743 0.706887 0.047 Uiso 1 1 calc R U . . .
C6 C 0.7328(7) 0.4498(3) 0.6388(3) 0.0388(10) Uani 1 1 d . . . . .
C1 C 0.6128(8) 0.4563(4) 0.5792(3) 0.0485(12) Uani 1 1 d . . . . .
H1A H 0.485827 0.437126 0.582993 0.058 Uiso 1 1 calc R U . . .
C11 C 0.2488(6) 0.5274(3) 0.8061(3) 0.0430(10) Uani 1 1 d . . . . .
C8 C 0.5801(6) 0.4887(3) 0.7597(2) 0.0373(9) Uani 1 1 d . . . . .
C7 C 0.6662(7) 0.4148(3) 0.7127(3) 0.0420(10) Uani 1 1 d . . . . .
H7 H 0.776647 0.388365 0.738294 0.050 Uiso 1 1 calc R U . . .
C9 C 0.6780(8) 0.5247(4) 0.8140(3) 0.0508(12) Uani 1 1 d . . . . .
H9A H 0.802062 0.504607 0.823766 0.061 Uiso 1 1 calc R U . . .
H9B H 0.622989 0.570282 0.842548 0.061 Uiso 1 1 calc R U . . .
C12 C 0.2038(8) 0.6196(3) 0.8346(4) 0.0544(12) Uani 1 1 d . U . . .
C5 C 0.9227(7) 0.4792(4) 0.6314(3) 0.0485(11) Uani 1 1 d . . . . .
H5 H 1.004513 0.476948 0.671386 0.058 Uiso 1 1 calc R U . . .
C15 C 0.1730(9) 0.2960(4) 0.8658(3) 0.0557(12) Uani 1 1 d . U . . .
C3 C 0.8697(10) 0.5179(4) 0.5073(3) 0.0607(15) Uani 1 1 d . . . . .
H3 H 0.915431 0.540395 0.463215 0.073 Uiso 1 1 calc R U . . .
C2 C 0.6800(10) 0.4914(4) 0.5132(3) 0.0602(15) Uani 1 1 d . . . . .
H2A H 0.597662 0.496846 0.473545 0.072 Uiso 1 1 calc R U . . .
C4 C 0.9907(9) 0.5115(4) 0.5656(3) 0.0593(14) Uani 1 1 d . . . . .
H4 H 1.118653 0.528784 0.561005 0.071 Uiso 1 1 calc R U . . .
C17 C -0.0410(10) 0.2854(5) 0.8685(4) 0.0698(17) Uani 1 1 d . U . . .
H17A H -0.098331 0.341924 0.883741 0.105 Uiso 1 1 calc R U . . .
H17B H -0.073969 0.237919 0.902395 0.105 Uiso 1 1 calc R U . . .
H17C H -0.087762 0.269448 0.820888 0.105 Uiso 1 1 calc R U . . .
C18 C 0.2417(13) 0.3090(6) 0.9436(5) 0.0821(19) Uani 1 1 d . U . . .
H18A H 0.375464 0.324973 0.943462 0.123 Uiso 1 1 calc R U . . .
H18B H 0.223967 0.253172 0.970357 0.123 Uiso 1 1 calc R U . . .
H18C H 0.169205 0.357064 0.966304 0.123 Uiso 1 1 calc R U . . .
C13 C 0.0500(15) 0.7119(6) 0.9268(5) 0.0880(18) Uani 1 1 d . U . . .
H13A H 0.033189 0.704533 0.978940 0.106 Uiso 1 1 calc R U . . .
H13B H 0.157581 0.752773 0.918511 0.106 Uiso 1 1 calc R U . . .
C16 C 0.2623(14) 0.2133(6) 0.8309(5) 0.087(2) Uani 1 1 d . U . . .
H16A H 0.179728 0.191084 0.792936 0.131 Uiso 1 1 calc R U . . .
H16B H 0.279674 0.166360 0.866931 0.131 Uiso 1 1 calc R U . . .
H16C H 0.384701 0.229575 0.810574 0.131 Uiso 1 1 calc R U . . .
C14 C -0.1179(16) 0.7485(7) 0.8956(6) 0.108(3) Uani 1 1 d . U . . .
H14A H -0.101714 0.753236 0.843730 0.162 Uiso 1 1 calc R U . . .
H14B H -0.141790 0.808079 0.915569 0.162 Uiso 1 1 calc R U . . .
H14C H -0.224658 0.709082 0.906079 0.162 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 H1 0.8200 . ?
O1 C7 1.441(6) . ?
O2 C12 1.224(6) . ?
N1 N2 1.320(6) . ?
N1 C11 1.307(6) . ?
N2 H2 0.8600 . ?
N2 C15 1.474(7) . ?
O3 C12 1.331(8) . ?
O3 C13 1.487(10) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 C11 1.490(7) . ?
C10 C8 1.525(6) . ?
C6 C1 1.380(7) . ?
C6 C7 1.522(7) . ?
C6 C5 1.397(7) . ?
C1 H1A 0.9300 . ?
C1 C2 1.395(8) . ?
C11 C12 1.479(7) . ?
C8 C7 1.507(7) . ?
C8 C9 1.316(7) . ?
C7 H7 0.9800 . ?
C9 H9A 0.9300 . ?
C9 H9B 0.9300 . ?
C5 H5 0.9300 . ?
C5 C4 1.379(8) . ?
C15 C17 1.498(9) . ?
C15 C18 1.517(10) . ?
C15 C16 1.503(10) . ?
C3 H3 0.9300 . ?
C3 C2 1.381(9) . ?
C3 C4 1.364(9) . ?
C2 H2A 0.9300 . ?
C4 H4 0.9300 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 C14 1.407(14) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 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
C7 O1 H1 109.5 . . ?
C11 N1 N2 118.0(4) . . ?
N1 N2 H2 120.7 . . ?
N1 N2 C15 118.5(5) . . ?
C15 N2 H2 120.7 . . ?
C12 O3 C13 117.8(6) . . ?
H10A C10 H10B 107.7 . . ?
C11 C10 H10A 108.8 . . ?
C11 C10 H10B 108.8 . . ?
C11 C10 C8 113.6(4) . . ?
C8 C10 H10A 108.8 . . ?
C8 C10 H10B 108.8 . . ?
C1 C6 C7 123.0(4) . . ?
C1 C6 C5 118.3(4) . . ?
C5 C6 C7 118.6(4) . . ?
C6 C1 H1A 119.7 . . ?
C6 C1 C2 120.7(5) . . ?
C2 C1 H1A 119.7 . . ?
N1 C11 C10 124.9(4) . . ?
N1 C11 C12 116.9(5) . . ?
C12 C11 C10 118.1(4) . . ?
C7 C8 C10 117.4(4) . . ?
C9 C8 C10 121.7(5) . . ?
C9 C8 C7 121.0(5) . . ?
O1 C7 C6 110.7(4) . . ?
O1 C7 C8 107.0(4) . . ?
O1 C7 H7 108.7 . . ?
C6 C7 H7 108.7 . . ?
C8 C7 C6 113.0(4) . . ?
C8 C7 H7 108.7 . . ?
C8 C9 H9A 120.0 . . ?
C8 C9 H9B 120.0 . . ?
H9A C9 H9B 120.0 . . ?
O2 C12 O3 123.4(5) . . ?
O2 C12 C11 121.2(5) . . ?
O3 C12 C11 115.4(4) . . ?
C6 C5 H5 119.5 . . ?
C4 C5 C6 121.0(5) . . ?
C4 C5 H5 119.5 . . ?
N2 C15 C17 109.8(5) . . ?
N2 C15 C18 111.6(5) . . ?
N2 C15 C16 106.4(5) . . ?
C17 C15 C18 107.3(6) . . ?
C17 C15 C16 110.0(6) . . ?
C16 C15 C18 111.8(6) . . ?
C2 C3 H3 119.7 . . ?
C4 C3 H3 119.7 . . ?
C4 C3 C2 120.7(5) . . ?
C1 C2 H2A 120.3 . . ?
C3 C2 C1 119.5(5) . . ?
C3 C2 H2A 120.3 . . ?
C5 C4 H4 120.1 . . ?
C3 C4 C5 119.8(5) . . ?
C3 C4 H4 120.1 . . ?
C15 C17 H17A 109.5 . . ?
C15 C17 H17B 109.5 . . ?
C15 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C15 C18 H18A 109.5 . . ?
C15 C18 H18B 109.5 . . ?
C15 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
O3 C13 H13A 110.1 . . ?
O3 C13 H13B 110.1 . . ?
H13A C13 H13B 108.4 . . ?
C14 C13 O3 108.1(8) . . ?
C14 C13 H13A 110.1 . . ?
C14 C13 H13B 110.1 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 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
N1 N2 C15 C17 68.6(7) . . . . ?
N1 N2 C15 C18 -50.3(8) . . . . ?
N1 N2 C15 C16 -172.5(6) . . . . ?
N1 C11 C12 O2 176.1(6) . . . . ?
N1 C11 C12 O3 -4.1(8) . . . . ?
N2 N1 C11 C10 -2.2(8) . . . . ?
N2 N1 C11 C12 -178.0(5) . . . . ?
C10 C11 C12 O2 0.0(9) . . . . ?
C10 C11 C12 O3 179.7(5) . . . . ?
C10 C8 C7 O1 -46.0(5) . . . . ?
C10 C8 C7 C6 76.2(5) . . . . ?
C6 C1 C2 C3 1.4(9) . . . . ?
C6 C5 C4 C3 2.3(9) . . . . ?
C1 C6 C7 O1 33.7(6) . . . . ?
C1 C6 C7 C8 -86.3(6) . . . . ?
C1 C6 C5 C4 -1.9(8) . . . . ?
C11 N1 N2 C15 171.2(5) . . . . ?
C11 C10 C8 C7 133.5(4) . . . . ?
C11 C10 C8 C9 -47.1(6) . . . . ?
C8 C10 C11 N1 -71.1(6) . . . . ?
C8 C10 C11 C12 104.8(5) . . . . ?
C7 C6 C1 C2 178.1(5) . . . . ?
C7 C6 C5 C4 179.9(5) . . . . ?
C9 C8 C7 O1 134.6(5) . . . . ?
C9 C8 C7 C6 -103.3(5) . . . . ?
C12 O3 C13 C14 93.0(9) . . . . ?
C5 C6 C1 C2 0.1(8) . . . . ?
C5 C6 C7 O1 -148.2(4) . . . . ?
C5 C6 C7 C8 91.7(5) . . . . ?
C2 C3 C4 C5 -0.8(9) . . . . ?
C4 C3 C2 C1 -1.0(9) . . . . ?
C13 O3 C12 O2 -5.0(10) . . . . ?
C13 O3 C12 C11 175.3(6) . . . . ?


_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 2(4)
2 -1(4)

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

data_1_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2183504'
loop_
_audit_author_name
_audit_author_address
'Jiaqing Xu'
;China Agricultural University
China
;
_audit_update_record             
;
2022-07-02 deposited with the CCDC.	2022-09-05 downloaded from the CCDC.
;
_audit_creation_date             2022-05-12
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.07.19 svn.r715e62df for OlexSys, GUI svn.r6383)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H20 N2 O2'
_chemical_formula_sum            'C20 H20 N2 O2'
_chemical_formula_weight         320.38
_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           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   8.1524(2)
_cell_length_b                   14.0253(4)
_cell_length_c                   15.1337(4)
_cell_angle_alpha                90
_cell_angle_beta                 102.5470(10)
_cell_angle_gamma                90
_cell_volume                     1689.06(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9962
_cell_measurement_temperature    298.00
_cell_measurement_theta_max      60.592
_cell_measurement_theta_min      3.781
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_T_max  0.7519
_exptl_absorpt_correction_T_min  0.5723
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1191 before and 0.0486 after correction.
The Ratio of minimum to maximum transmission is 0.7611.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.260
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             680
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0358
_diffrn_reflns_av_unetI/netI     0.0293
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            17254
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.500
_diffrn_reflns_theta_min         2.002
_diffrn_ambient_temperature      298.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.987
_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_source_current           2.86
_diffrn_source_power             0.1997996
_diffrn_source_voltage           69.86
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3170
_reflns_number_total             3838
_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 V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.189
_refine_diff_density_min         -0.161
_refine_diff_density_rms         0.032
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         3838
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0491
_refine_ls_R_factor_gt           0.0392
_refine_ls_restrained_S_all      1.040
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0489P)²+0.3292P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0987
_refine_ls_wR_factor_ref         0.1050
_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 Ternary CH refined with riding coordinates:
 C8(H8)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C5(H5A,H5B)
2.c Aromatic/amide H refined with riding coordinates:
 C10(H10), C11(H11), C12(H12), C13(H13), C14(H14), C16(H16), C17(H17),
 C18(H18), C19(H19), C20(H20)
2.d X=CH2 refined with riding coordinates:
 C7(H7A,H7B)
2.e Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
;
_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 0.11084(12) 0.65660(6) 0.44985(6) 0.0457(2) Uani 1 1 d . . . . .
O2 O 0.23141(11) 0.51573(6) 0.49519(5) 0.0400(2) Uani 1 1 d . . . . .
N1 N 0.35303(11) 0.58628(6) 0.65865(6) 0.0290(2) Uani 1 1 d . . . . .
N2 N 0.41962(11) 0.61614(6) 0.74353(6) 0.0289(2) Uani 1 1 d . . . . .
C1 C 0.2252(2) 0.37953(11) 0.39997(10) 0.0560(4) Uani 1 1 d . . . . .
H1A H 0.184117 0.354608 0.340176 0.084 Uiso 1 1 calc R U . . .
H1B H 0.182939 0.341578 0.442918 0.084 Uiso 1 1 calc R U . . .
H1C H 0.345782 0.377739 0.414274 0.084 Uiso 1 1 calc R U . . .
C2 C 0.16720(17) 0.48012(9) 0.40395(8) 0.0421(3) Uani 1 1 d . . . . .
H2A H 0.208825 0.518985 0.360532 0.050 Uiso 1 1 calc R U . . .
H2B H 0.045393 0.482688 0.389317 0.050 Uiso 1 1 calc R U . . .
C3 C 0.19398(14) 0.60682(8) 0.50838(7) 0.0335(2) Uani 1 1 d . . . . .
C4 C 0.26246(13) 0.64369(8) 0.60071(7) 0.0312(2) Uani 1 1 d . . . . .
C5 C 0.22646(16) 0.74623(8) 0.61857(8) 0.0369(3) Uani 1 1 d . . . . .
H5A H 0.233837 0.784969 0.566477 0.044 Uiso 1 1 calc R U . . .
H5B H 0.113737 0.752166 0.629142 0.044 Uiso 1 1 calc R U . . .
C6 C 0.35177(14) 0.77973(8) 0.69978(8) 0.0331(2) Uani 1 1 d . . . . .
C7 C 0.43588(18) 0.86054(9) 0.70432(10) 0.0490(3) Uani 1 1 d . . . . .
H7A H 0.418875 0.901166 0.654591 0.059 Uiso 1 1 calc R U . . .
H7B H 0.512212 0.876899 0.757245 0.059 Uiso 1 1 calc R U . . .
C8 C 0.37812(13) 0.70965(7) 0.77734(7) 0.0288(2) Uani 1 1 d . . . . .
H8 H 0.474017 0.731127 0.823982 0.035 Uiso 1 1 calc R U . . .
C9 C 0.22379(13) 0.70414(7) 0.81926(7) 0.0276(2) Uani 1 1 d . . . . .
C10 C 0.17957(15) 0.78401(8) 0.86329(8) 0.0351(3) Uani 1 1 d . . . . .
H10 H 0.246701 0.838255 0.869251 0.042 Uiso 1 1 calc R U . . .
C11 C 0.03594(15) 0.78325(9) 0.89835(8) 0.0389(3) Uani 1 1 d . . . . .
H11 H 0.006967 0.837086 0.927436 0.047 Uiso 1 1 calc R U . . .
C12 C -0.06453(15) 0.70281(9) 0.89029(8) 0.0387(3) Uani 1 1 d . . . . .
H12 H -0.161531 0.702838 0.913218 0.046 Uiso 1 1 calc R U . . .
C13 C -0.02014(15) 0.62234(9) 0.84801(8) 0.0385(3) Uani 1 1 d . . . . .
H13 H -0.086287 0.567782 0.843412 0.046 Uiso 1 1 calc R U . . .
C14 C 0.12335(14) 0.62308(8) 0.81240(7) 0.0328(2) Uani 1 1 d . . . . .
H14 H 0.152460 0.568962 0.783770 0.039 Uiso 1 1 calc R U . . .
C15 C 0.51522(12) 0.54812(7) 0.80242(7) 0.0288(2) Uani 1 1 d . . . . .
C16 C 0.56759(14) 0.56628(9) 0.89470(7) 0.0349(3) Uani 1 1 d . . . . .
H16 H 0.537867 0.623023 0.918902 0.042 Uiso 1 1 calc R U . . .
C17 C 0.66451(15) 0.49921(9) 0.95048(9) 0.0423(3) Uani 1 1 d . . . . .
H17 H 0.701347 0.512302 1.011834 0.051 Uiso 1 1 calc R U . . .
C18 C 0.70709(16) 0.41361(10) 0.91657(9) 0.0465(3) Uani 1 1 d . . . . .
H18 H 0.771591 0.369064 0.954480 0.056 Uiso 1 1 calc R U . . .
C19 C 0.65205(16) 0.39527(9) 0.82514(9) 0.0448(3) Uani 1 1 d . . . . .
H19 H 0.678602 0.337368 0.801748 0.054 Uiso 1 1 calc R U . . .
C20 C 0.55811(14) 0.46162(8) 0.76786(8) 0.0367(3) Uani 1 1 d . . . . .
H20 H 0.523589 0.448557 0.706375 0.044 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 C3 1.2127(14) . ?
O2 C2 1.4547(14) . ?
O2 C3 1.3385(14) . ?
N1 N2 1.3480(12) . ?
N1 C4 1.2966(14) . ?
N2 C8 1.4736(13) . ?
N2 C15 1.4177(13) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C1 C2 1.4932(19) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.4808(15) . ?
C4 C5 1.5039(16) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C5 C6 1.4931(16) . ?
C6 C7 1.3187(17) . ?
C6 C8 1.5102(15) . ?
C7 H7A 0.9300 . ?
C7 H7B 0.9300 . ?
C8 H8 0.9800 . ?
C8 C9 1.5291(14) . ?
C9 C10 1.3904(15) . ?
C9 C14 1.3917(15) . ?
C10 H10 0.9300 . ?
C10 C11 1.3866(17) . ?
C11 H11 0.9300 . ?
C11 C12 1.3839(17) . ?
C12 H12 0.9300 . ?
C12 C13 1.3837(17) . ?
C13 H13 0.9300 . ?
C13 C14 1.3903(16) . ?
C14 H14 0.9300 . ?
C15 C16 1.3922(16) . ?
C15 C20 1.3954(16) . ?
C16 H16 0.9300 . ?
C16 C17 1.3899(16) . ?
C17 H17 0.9300 . ?
C17 C18 1.3794(19) . ?
C18 H18 0.9300 . ?
C18 C19 1.383(2) . ?
C19 H19 0.9300 . ?
C19 C20 1.3840(17) . ?
C20 H20 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 O2 C2 115.00(9) . . ?
C4 N1 N2 120.25(9) . . ?
N1 N2 C8 122.14(8) . . ?
N1 N2 C15 116.27(9) . . ?
C15 N2 C8 121.13(8) . . ?
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 . . ?
O2 C2 C1 108.11(10) . . ?
O2 C2 H2A 110.1 . . ?
O2 C2 H2B 110.1 . . ?
C1 C2 H2A 110.1 . . ?
C1 C2 H2B 110.1 . . ?
H2A C2 H2B 108.4 . . ?
O1 C3 O2 123.37(10) . . ?
O1 C3 C4 121.63(11) . . ?
O2 C3 C4 115.00(9) . . ?
N1 C4 C3 117.63(10) . . ?
N1 C4 C5 125.24(10) . . ?
C3 C4 C5 117.08(9) . . ?
C4 C5 H5A 109.9 . . ?
C4 C5 H5B 109.9 . . ?
H5A C5 H5B 108.3 . . ?
C6 C5 C4 108.87(9) . . ?
C6 C5 H5A 109.9 . . ?
C6 C5 H5B 109.9 . . ?
C5 C6 C8 113.04(9) . . ?
C7 C6 C5 124.64(11) . . ?
C7 C6 C8 122.30(11) . . ?
C6 C7 H7A 120.0 . . ?
C6 C7 H7B 120.0 . . ?
H7A C7 H7B 120.0 . . ?
N2 C8 C6 108.30(8) . . ?
N2 C8 H8 108.4 . . ?
N2 C8 C9 111.76(8) . . ?
C6 C8 H8 108.4 . . ?
C6 C8 C9 111.37(9) . . ?
C9 C8 H8 108.4 . . ?
C10 C9 C8 118.72(9) . . ?
C10 C9 C14 118.97(10) . . ?
C14 C9 C8 122.29(9) . . ?
C9 C10 H10 119.8 . . ?
C11 C10 C9 120.37(11) . . ?
C11 C10 H10 119.8 . . ?
C10 C11 H11 119.8 . . ?
C12 C11 C10 120.36(11) . . ?
C12 C11 H11 119.8 . . ?
C11 C12 H12 120.1 . . ?
C13 C12 C11 119.76(11) . . ?
C13 C12 H12 120.1 . . ?
C12 C13 H13 120.0 . . ?
C12 C13 C14 119.98(11) . . ?
C14 C13 H13 120.0 . . ?
C9 C14 H14 119.7 . . ?
C13 C14 C9 120.54(10) . . ?
C13 C14 H14 119.7 . . ?
C16 C15 N2 120.95(10) . . ?
C16 C15 C20 119.19(10) . . ?
C20 C15 N2 119.85(10) . . ?
C15 C16 H16 120.2 . . ?
C17 C16 C15 119.70(11) . . ?
C17 C16 H16 120.2 . . ?
C16 C17 H17 119.4 . . ?
C18 C17 C16 121.25(12) . . ?
C18 C17 H17 119.4 . . ?
C17 C18 H18 120.6 . . ?
C17 C18 C19 118.75(11) . . ?
C19 C18 H18 120.6 . . ?
C18 C19 H19 119.4 . . ?
C18 C19 C20 121.11(12) . . ?
C20 C19 H19 119.4 . . ?
C15 C20 H20 120.0 . . ?
C19 C20 C15 119.97(11) . . ?
C19 C20 H20 120.0 . . ?

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 C3 C4 N1 -178.57(10) . . . . ?
O1 C3 C4 C5 -0.82(16) . . . . ?
O2 C3 C4 N1 1.21(14) . . . . ?
O2 C3 C4 C5 178.97(9) . . . . ?
N1 N2 C8 C6 -34.14(12) . . . . ?
N1 N2 C8 C9 88.91(11) . . . . ?
N1 N2 C15 C16 -169.98(9) . . . . ?
N1 N2 C15 C20 10.10(14) . . . . ?
N1 C4 C5 C6 17.96(15) . . . . ?
N2 N1 C4 C3 179.55(9) . . . . ?
N2 N1 C4 C5 2.00(16) . . . . ?
N2 C8 C9 C10 172.92(9) . . . . ?
N2 C8 C9 C14 -9.11(14) . . . . ?
N2 C15 C16 C17 -178.51(10) . . . . ?
N2 C15 C20 C19 179.72(10) . . . . ?
C2 O2 C3 O1 1.05(16) . . . . ?
C2 O2 C3 C4 -178.73(9) . . . . ?
C3 O2 C2 C1 177.89(11) . . . . ?
C3 C4 C5 C6 -159.60(10) . . . . ?
C4 N1 N2 C8 7.04(14) . . . . ?
C4 N1 N2 C15 179.32(9) . . . . ?
C4 C5 C6 C7 132.68(13) . . . . ?
C4 C5 C6 C8 -45.56(13) . . . . ?
C5 C6 C8 N2 53.39(12) . . . . ?
C5 C6 C8 C9 -69.90(12) . . . . ?
C6 C8 C9 C10 -65.79(12) . . . . ?
C6 C8 C9 C14 112.17(11) . . . . ?
C7 C6 C8 N2 -124.90(12) . . . . ?
C7 C6 C8 C9 111.81(13) . . . . ?
C8 N2 C15 C16 2.39(14) . . . . ?
C8 N2 C15 C20 -177.53(9) . . . . ?
C8 C9 C10 C11 176.91(10) . . . . ?
C8 C9 C14 C13 -177.15(10) . . . . ?
C9 C10 C11 C12 0.32(18) . . . . ?
C10 C9 C14 C13 0.80(16) . . . . ?
C10 C11 C12 C13 0.82(18) . . . . ?
C11 C12 C13 C14 -1.13(18) . . . . ?
C12 C13 C14 C9 0.32(17) . . . . ?
C14 C9 C10 C11 -1.12(16) . . . . ?
C15 N2 C8 C6 153.95(9) . . . . ?
C15 N2 C8 C9 -83.00(11) . . . . ?
C15 C16 C17 C18 -1.47(18) . . . . ?
C16 C15 C20 C19 -0.20(17) . . . . ?
C16 C17 C18 C19 0.27(19) . . . . ?
C17 C18 C19 C20 0.97(19) . . . . ?
C18 C19 C20 C15 -1.01(19) . . . . ?
C20 C15 C16 C17 1.41(16) . . . . ?


_olex2_submission_special_instructions 'No special instructions were received'
