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

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
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data_mo_230612_zy_5_80_0m
_database_code_depnum_ccdc_archive 'CCDC 2365302'
loop_
_audit_author_name
_audit_author_address
'Yu Zhu'
;Zhejiang University of Technology
China
;
_audit_update_record             
;
2024-06-25 deposited with the CCDC.	2025-01-21 downloaded from the CCDC.
;
_audit_creation_date             2023-06-14
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2019/2
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C26 H26 N2 O2'
_chemical_formula_sum            'C26 H26 N2 O2'
_chemical_formula_weight         398.49
_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                   7.8217(3)
_cell_length_b                   28.8712(10)
_cell_length_c                   10.0160(3)
_cell_angle_alpha                90
_cell_angle_beta                 109.4000(10)
_cell_angle_gamma                90
_cell_volume                     2133.41(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9914
_cell_measurement_temperature    170.00
_cell_measurement_theta_max      27.416
_cell_measurement_theta_min      2.576
_shelx_estimated_absorpt_T_max   0.982
_shelx_estimated_absorpt_T_min   0.968
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.7081
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1469 before and 0.0768 after correction.
The Ratio of minimum to maximum transmission is 0.9497.
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    1.241
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             848
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.23
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0407
_diffrn_reflns_av_unetI/netI     0.0265
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       37
_diffrn_reflns_limit_k_min       -37
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            30701
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.495
_diffrn_reflns_theta_min         2.268
_diffrn_ambient_temperature      170.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'zju Bruker D8 Venture'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3974
_reflns_number_total             4889
_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 (Bruker Nano, Inc., 2019)'
_computing_data_collection       'Bruker Instrument Service vV6.2.14'
_computing_data_reduction        'SAINT V8.40B (Bruker Nano, Inc., 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/2 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.180
_refine_diff_density_min         -0.178
_refine_diff_density_rms         0.039
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     281
_refine_ls_number_reflns         4889
_refine_ls_number_restraints     21
_refine_ls_R_factor_all          0.0602
_refine_ls_R_factor_gt           0.0458
_refine_ls_restrained_S_all      1.059
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0374P)²+0.7411P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1005
_refine_ls_wR_factor_ref         0.1108
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
2. Restrained distances
 O1-N1 \\sim O1-N1A
 with sigma of 0.02
 N1-C6 \\sim N1A-C6
 with sigma of 0.02
 N1-C7 \\sim N1A-C7
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
C6 \\sim N1 \\sim N1A: within 2A with sigma of 0.01 and sigma for terminal
atoms of 0.02 within 2A
4. Others
 Sof(H7BC)=Sof(H7BD)=Sof(N1A)=1-FVAR(1)
 Sof(H7AA)=Sof(H7AB)=Sof(N1)=FVAR(1)
5.a Ternary CH refined with riding coordinates:
 C8(H8)
5.b Secondary CH2 refined with riding coordinates:
 C7(H7AA,H7AB), C7(H7BC,H7BD), C9(H9A,H9B), C11(H11A,H11B), C13(H13A,H13B),
 C20(H20A,H20B)
5.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C15(H15), C16(H16), C17(H17),
 C18(H18), C19(H19), C22(H22), C23(H23), C24(H24), C25(H25), C26(H26)
;
_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 0.77590(12) 0.59907(3) 0.74914(10) 0.0349(2) Uani 1 1 d D . . . .
O2 O 0.43214(14) 0.53301(4) 0.61865(11) 0.0438(3) Uani 1 1 d . . . . .
N2 N 0.47448(14) 0.59323(4) 0.48861(11) 0.0303(2) Uani 1 1 d . . . . .
C1 C 0.86630(19) 0.68459(5) 0.84742(16) 0.0382(3) Uani 1 1 d . . . . .
H1 H 0.759208 0.680961 0.768031 0.046 Uiso 1 1 calc R U . . .
C2 C 0.8960(2) 0.72540(5) 0.92377(16) 0.0425(3) Uani 1 1 d . . . . .
H2 H 0.809118 0.749637 0.896425 0.051 Uiso 1 1 calc R U . . .
C3 C 1.0511(2) 0.73127(6) 1.03964(18) 0.0491(4) Uani 1 1 d . . . . .
H3 H 1.071265 0.759375 1.091896 0.059 Uiso 1 1 calc R U . . .
C4 C 1.1758(2) 0.69595(6) 1.07837(18) 0.0508(4) Uani 1 1 d . . . . .
H4 H 1.282814 0.699951 1.157629 0.061 Uiso 1 1 calc R U . . .
C5 C 1.1482(2) 0.65452(5) 1.00367(17) 0.0445(4) Uani 1 1 d . . . . .
H5 H 1.234891 0.630293 1.032481 0.053 Uiso 1 1 calc R U . . .
C6 C 0.99245(18) 0.64869(5) 0.88611(15) 0.0369(3) Uani 1 1 d D U . . .
C7 C 1.0797(2) 0.56850(5) 0.84868(18) 0.0496(4) Uani 1 1 d D . . . .
H7AA H 1.085244 0.561699 0.946924 0.060 Uiso 0.871(7) 1 calc R U P A 1
H7AB H 1.204494 0.573992 0.848467 0.060 Uiso 0.871(7) 1 calc R U P A 1
H7BC H 1.151751 0.556558 0.943310 0.060 Uiso 0.129(7) 1 calc R U P A 2
H7BD H 1.163136 0.585124 0.809583 0.060 Uiso 0.129(7) 1 calc R U P A 2
C8 C 0.9948(2) 0.52775(6) 0.75209(18) 0.0504(4) Uani 1 1 d . . . . .
H8 H 1.076740 0.500836 0.755862 0.061 Uiso 1 1 calc R U . . .
C9 C 0.8879(2) 0.54614(6) 0.60243(16) 0.0433(4) Uani 1 1 d . . . . .
H9A H 0.854972 0.522191 0.527454 0.052 Uiso 1 1 calc R U . . .
H9B H 0.941677 0.573798 0.573379 0.052 Uiso 1 1 calc R U . . .
C10 C 0.73779(18) 0.55693(5) 0.66745(14) 0.0327(3) Uani 1 1 d . . . . .
C11 C 0.8096(2) 0.51603(5) 0.76805(17) 0.0463(4) Uani 1 1 d . . . . .
H11A H 0.759578 0.485541 0.728870 0.056 Uiso 1 1 calc R U . . .
H11B H 0.804599 0.520631 0.864631 0.056 Uiso 1 1 calc R U . . .
C12 C 0.53493(18) 0.55970(4) 0.58717(13) 0.0309(3) Uani 1 1 d . . . . .
C13 C 0.28000(18) 0.60159(5) 0.42782(14) 0.0344(3) Uani 1 1 d . . . . .
H13A H 0.213976 0.573690 0.441325 0.041 Uiso 1 1 calc R U . . .
H13B H 0.248137 0.606903 0.324771 0.041 Uiso 1 1 calc R U . . .
C14 C 0.21942(18) 0.64289(5) 0.49403(15) 0.0347(3) Uani 1 1 d . . . . .
C15 C 0.0699(2) 0.66807(6) 0.4157(2) 0.0496(4) Uani 1 1 d . . . . .
H15 H 0.009046 0.660469 0.319229 0.059 Uiso 1 1 calc R U . . .
C16 C 0.0082(3) 0.70469(6) 0.4782(3) 0.0676(6) Uani 1 1 d . . . . .
H16 H -0.095869 0.721720 0.424511 0.081 Uiso 1 1 calc R U . . .
C17 C 0.0968(3) 0.71625(6) 0.6167(3) 0.0700(6) Uani 1 1 d . . . . .
H17 H 0.054223 0.741260 0.658723 0.084 Uiso 1 1 calc R U . . .
C18 C 0.2465(3) 0.69182(6) 0.6945(2) 0.0632(5) Uani 1 1 d . . . . .
H18 H 0.308495 0.700067 0.790226 0.076 Uiso 1 1 calc R U . . .
C19 C 0.3080(2) 0.65515(6) 0.63413(17) 0.0476(4) Uani 1 1 d . . . . .
H19 H 0.411591 0.638186 0.688936 0.057 Uiso 1 1 calc R U . . .
C20 C 0.58938(18) 0.62543(5) 0.44464(14) 0.0335(3) Uani 1 1 d . . . . .
H20A H 0.714122 0.623823 0.513134 0.040 Uiso 1 1 calc R U . . .
H20B H 0.544126 0.657341 0.446962 0.040 Uiso 1 1 calc R U . . .
C21 C 0.59492(17) 0.61550(5) 0.29764(14) 0.0318(3) Uani 1 1 d . . . . .
C22 C 0.5820(2) 0.57088(5) 0.24426(15) 0.0393(3) Uani 1 1 d . . . . .
H22 H 0.563663 0.545513 0.298407 0.047 Uiso 1 1 calc R U . . .
C23 C 0.5960(2) 0.56336(7) 0.11118(17) 0.0519(4) Uani 1 1 d . . . . .
H23 H 0.586767 0.532798 0.074310 0.062 Uiso 1 1 calc R U . . .
C24 C 0.6232(2) 0.60026(8) 0.03204(18) 0.0618(5) Uani 1 1 d . . . . .
H24 H 0.633222 0.595006 -0.058706 0.074 Uiso 1 1 calc R U . . .
C25 C 0.6357(2) 0.64439(8) 0.08519(19) 0.0604(5) Uani 1 1 d . . . . .
H25 H 0.654574 0.669740 0.031251 0.073 Uiso 1 1 calc R U . . .
C26 C 0.6209(2) 0.65196(6) 0.21622(16) 0.0440(4) Uani 1 1 d . . . . .
H26 H 0.628676 0.682676 0.251749 0.053 Uiso 1 1 calc R U . . .
N1 N 0.96767(19) 0.60935(6) 0.7959(3) 0.0361(5) Uani 0.871(7) 1 d D U P A 1
N1A N 0.9460(12) 0.6004(3) 0.8633(15) 0.033(3) Uani 0.129(7) 1 d D U P A 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C10 1.4408(15) . ?
O1 N1 1.4460(17) . ?
O1 N1A 1.438(9) . ?
O2 C12 1.2280(16) . ?
N2 C12 1.3509(17) . ?
N2 C13 1.4587(16) . ?
N2 C20 1.4592(16) . ?
C1 H1 0.9500 . ?
C1 C2 1.382(2) . ?
C1 C6 1.3942(19) . ?
C2 H2 0.9500 . ?
C2 C3 1.383(2) . ?
C3 H3 0.9500 . ?
C3 C4 1.375(2) . ?
C4 H4 0.9500 . ?
C4 C5 1.389(2) . ?
C5 H5 0.9500 . ?
C5 C6 1.395(2) . ?
C6 N1 1.424(2) . ?
C6 N1A 1.441(10) . ?
C7 H7AA 0.9900 . ?
C7 H7AB 0.9900 . ?
C7 H7BC 0.9900 . ?
C7 H7BD 0.9900 . ?
C7 C8 1.528(2) . ?
C7 N1 1.460(2) . ?
C7 N1A 1.436(10) . ?
C8 H8 1.0000 . ?
C8 C9 1.548(2) . ?
C8 C11 1.547(2) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.5519(19) . ?
C10 C11 1.5328(19) . ?
C10 C12 1.5241(18) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C13 C14 1.5149(18) . ?
C14 C15 1.379(2) . ?
C14 C19 1.389(2) . ?
C15 H15 0.9500 . ?
C15 C16 1.394(2) . ?
C16 H16 0.9500 . ?
C16 C17 1.370(3) . ?
C17 H17 0.9500 . ?
C17 C18 1.368(3) . ?
C18 H18 0.9500 . ?
C18 C19 1.382(2) . ?
C19 H19 0.9500 . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C20 C21 1.5146(18) . ?
C21 C22 1.386(2) . ?
C21 C26 1.3874(19) . ?
C22 H22 0.9500 . ?
C22 C23 1.390(2) . ?
C23 H23 0.9500 . ?
C23 C24 1.386(3) . ?
C24 H24 0.9500 . ?
C24 C25 1.372(3) . ?
C25 H25 0.9500 . ?
C25 C26 1.373(2) . ?
C26 H26 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C10 O1 N1 110.73(10) . . ?
N1A O1 C10 115.8(3) . . ?
C12 N2 C13 119.14(11) . . ?
C12 N2 C20 125.17(11) . . ?
C13 N2 C20 115.47(11) . . ?
C2 C1 H1 119.8 . . ?
C2 C1 C6 120.45(14) . . ?
C6 C1 H1 119.8 . . ?
C1 C2 H2 119.7 . . ?
C1 C2 C3 120.54(14) . . ?
C3 C2 H2 119.7 . . ?
C2 C3 H3 120.4 . . ?
C4 C3 C2 119.24(15) . . ?
C4 C3 H3 120.4 . . ?
C3 C4 H4 119.4 . . ?
C3 C4 C5 121.18(15) . . ?
C5 C4 H4 119.4 . . ?
C4 C5 H5 120.2 . . ?
C4 C5 C6 119.64(14) . . ?
C6 C5 H5 120.2 . . ?
C1 C6 C5 118.94(13) . . ?
C1 C6 N1 118.81(13) . . ?
C1 C6 N1A 123.9(4) . . ?
C5 C6 N1 121.90(13) . . ?
C5 C6 N1A 110.7(4) . . ?
H7AA C7 H7AB 108.4 . . ?
H7BC C7 H7BD 107.9 . . ?
C8 C7 H7AA 110.1 . . ?
C8 C7 H7AB 110.1 . . ?
C8 C7 H7BC 109.1 . . ?
C8 C7 H7BD 109.1 . . ?
N1 C7 H7AA 110.1 . . ?
N1 C7 H7AB 110.1 . . ?
N1 C7 C8 108.10(13) . . ?
N1A C7 H7BC 109.1 . . ?
N1A C7 H7BD 109.1 . . ?
N1A C7 C8 112.3(4) . . ?
C7 C8 H8 115.9 . . ?
C7 C8 C9 109.30(13) . . ?
C7 C8 C11 109.13(13) . . ?
C9 C8 H8 115.9 . . ?
C11 C8 H8 115.9 . . ?
C11 C8 C9 87.25(11) . . ?
C8 C9 H9A 114.6 . . ?
C8 C9 H9B 114.6 . . ?
C8 C9 C10 84.44(11) . . ?
H9A C9 H9B 111.7 . . ?
C10 C9 H9A 114.6 . . ?
C10 C9 H9B 114.6 . . ?
O1 C10 C9 111.41(11) . . ?
O1 C10 C11 108.40(11) . . ?
O1 C10 C12 103.78(10) . . ?
C11 C10 C9 87.59(11) . . ?
C12 C10 C9 126.12(11) . . ?
C12 C10 C11 118.50(12) . . ?
C8 C11 H11A 114.5 . . ?
C8 C11 H11B 114.5 . . ?
C10 C11 C8 85.11(12) . . ?
C10 C11 H11A 114.5 . . ?
C10 C11 H11B 114.5 . . ?
H11A C11 H11B 111.6 . . ?
O2 C12 N2 122.49(12) . . ?
O2 C12 C10 119.16(12) . . ?
N2 C12 C10 118.26(11) . . ?
N2 C13 H13A 109.1 . . ?
N2 C13 H13B 109.1 . . ?
N2 C13 C14 112.45(11) . . ?
H13A C13 H13B 107.8 . . ?
C14 C13 H13A 109.1 . . ?
C14 C13 H13B 109.1 . . ?
C15 C14 C13 119.68(13) . . ?
C15 C14 C19 118.99(14) . . ?
C19 C14 C13 121.30(13) . . ?
C14 C15 H15 120.0 . . ?
C14 C15 C16 119.92(18) . . ?
C16 C15 H15 120.0 . . ?
C15 C16 H16 119.8 . . ?
C17 C16 C15 120.35(19) . . ?
C17 C16 H16 119.8 . . ?
C16 C17 H17 120.0 . . ?
C18 C17 C16 120.04(17) . . ?
C18 C17 H17 120.0 . . ?
C17 C18 H18 119.9 . . ?
C17 C18 C19 120.16(19) . . ?
C19 C18 H18 119.9 . . ?
C14 C19 H19 119.7 . . ?
C18 C19 C14 120.54(17) . . ?
C18 C19 H19 119.7 . . ?
N2 C20 H20A 109.0 . . ?
N2 C20 H20B 109.0 . . ?
N2 C20 C21 113.09(11) . . ?
H20A C20 H20B 107.8 . . ?
C21 C20 H20A 109.0 . . ?
C21 C20 H20B 109.0 . . ?
C22 C21 C20 121.95(12) . . ?
C22 C21 C26 119.00(13) . . ?
C26 C21 C20 119.00(13) . . ?
C21 C22 H22 120.1 . . ?
C21 C22 C23 119.75(14) . . ?
C23 C22 H22 120.1 . . ?
C22 C23 H23 119.9 . . ?
C24 C23 C22 120.30(17) . . ?
C24 C23 H23 119.9 . . ?
C23 C24 H24 120.1 . . ?
C25 C24 C23 119.77(15) . . ?
C25 C24 H24 120.1 . . ?
C24 C25 H25 120.0 . . ?
C24 C25 C26 120.08(16) . . ?
C26 C25 H25 120.0 . . ?
C21 C26 H26 119.5 . . ?
C25 C26 C21 121.10(16) . . ?
C25 C26 H26 119.5 . . ?
O1 N1 C7 112.61(15) . . ?
C6 N1 O1 106.09(13) . . ?
C6 N1 C7 118.42(16) . . ?
O1 N1A C6 105.6(7) . . ?
C7 N1A O1 114.5(7) . . ?
C7 N1A C6 118.9(9) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C10 C11 C8 -82.50(12) . . . . ?
O1 C10 C12 O2 -110.54(13) . . . . ?
O1 C10 C12 N2 66.10(14) . . . . ?
N2 C13 C14 C15 151.43(13) . . . . ?
N2 C13 C14 C19 -30.71(18) . . . . ?
N2 C20 C21 C22 -32.71(18) . . . . ?
N2 C20 C21 C26 149.91(12) . . . . ?
C1 C2 C3 C4 -0.1(2) . . . . ?
C1 C6 N1 O1 -41.2(2) . . . . ?
C1 C6 N1 C7 -168.89(17) . . . . ?
C1 C6 N1A O1 23.3(13) . . . . ?
C1 C6 N1A C7 153.5(6) . . . . ?
C2 C1 C6 C5 0.5(2) . . . . ?
C2 C1 C6 N1 -172.91(17) . . . . ?
C2 C1 C6 N1A 149.7(8) . . . . ?
C2 C3 C4 C5 -0.3(3) . . . . ?
C3 C4 C5 C6 0.8(3) . . . . ?
C4 C5 C6 C1 -0.9(2) . . . . ?
C4 C5 C6 N1 172.31(19) . . . . ?
C4 C5 C6 N1A -153.9(7) . . . . ?
C5 C6 N1 O1 145.57(15) . . . . ?
C5 C6 N1 C7 17.9(3) . . . . ?
C5 C6 N1A O1 174.7(6) . . . . ?
C5 C6 N1A C7 -55.1(13) . . . . ?
C6 C1 C2 C3 0.0(2) . . . . ?
C7 C8 C9 C10 -80.30(14) . . . . ?
C7 C8 C11 C10 80.11(13) . . . . ?
C8 C7 N1 O1 40.4(2) . . . . ?
C8 C7 N1 C6 164.91(17) . . . . ?
C8 C7 N1A O1 -23.2(13) . . . . ?
C8 C7 N1A C6 -149.3(8) . . . . ?
C8 C9 C10 O1 79.54(12) . . . . ?
C8 C9 C10 C11 -29.30(11) . . . . ?
C8 C9 C10 C12 -153.39(13) . . . . ?
C9 C8 C11 C10 -29.38(10) . . . . ?
C9 C10 C11 C8 29.28(11) . . . . ?
C9 C10 C12 O2 119.35(15) . . . . ?
C9 C10 C12 N2 -64.01(18) . . . . ?
C10 O1 N1 C6 -174.52(14) . . . . ?
C10 O1 N1 C7 -43.5(2) . . . . ?
C10 O1 N1A C6 154.7(6) . . . . ?
C10 O1 N1A C7 22.0(13) . . . . ?
C11 C8 C9 C10 29.02(10) . . . . ?
C11 C10 C12 O2 9.66(18) . . . . ?
C11 C10 C12 N2 -173.70(12) . . . . ?
C12 N2 C13 C14 100.17(14) . . . . ?
C12 N2 C20 C21 108.03(14) . . . . ?
C12 C10 C11 C8 159.71(12) . . . . ?
C13 N2 C12 O2 6.83(19) . . . . ?
C13 N2 C12 C10 -169.70(11) . . . . ?
C13 N2 C20 C21 -77.45(14) . . . . ?
C13 C14 C15 C16 176.82(14) . . . . ?
C13 C14 C19 C18 -177.44(14) . . . . ?
C14 C15 C16 C17 0.9(3) . . . . ?
C15 C14 C19 C18 0.4(2) . . . . ?
C15 C16 C17 C18 -0.1(3) . . . . ?
C16 C17 C18 C19 -0.6(3) . . . . ?
C17 C18 C19 C14 0.4(3) . . . . ?
C19 C14 C15 C16 -1.1(2) . . . . ?
C20 N2 C12 O2 -178.83(12) . . . . ?
C20 N2 C12 C10 4.65(18) . . . . ?
C20 N2 C13 C14 -74.71(14) . . . . ?
C20 C21 C22 C23 -177.12(13) . . . . ?
C20 C21 C26 C25 176.82(14) . . . . ?
C21 C22 C23 C24 0.2(2) . . . . ?
C22 C21 C26 C25 -0.6(2) . . . . ?
C22 C23 C24 C25 -0.3(3) . . . . ?
C23 C24 C25 C26 -0.1(3) . . . . ?
C24 C25 C26 C21 0.6(3) . . . . ?
C26 C21 C22 C23 0.3(2) . . . . ?
N1 O1 C10 C9 -23.19(18) . . . . ?
N1 O1 C10 C11 71.56(17) . . . . ?
N1 O1 C10 C12 -161.62(14) . . . . ?
N1 C7 C8 C9 27.3(2) . . . . ?
N1 C7 C8 C11 -66.5(2) . . . . ?
N1A O1 C10 C9 -57.6(8) . . . . ?
N1A O1 C10 C11 37.2(8) . . . . ?
N1A O1 C10 C12 164.0(8) . . . . ?
N1A C7 C8 C9 60.9(8) . . . . ?
N1A C7 C8 C11 -32.9(8) . . . . ?

_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_240325_zy_6_142
_database_code_depnum_ccdc_archive 'CCDC 2365303'
loop_
_audit_author_name
_audit_author_address
'Yu Zhu'
;Zhejiang University of Technology
China
;
_audit_update_record             
;
2024-06-25 deposited with the CCDC.	2025-01-21 downloaded from the CCDC.
;
_audit_creation_date             2024-03-26
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2019/2
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H24 N2 O3'
_chemical_formula_sum            'C22 H24 N2 O3'
_chemical_formula_weight         364.43
_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 0.0137 0.0067 '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 0.0241 0.0134 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0389 0.0241 '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           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'
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'

_cell_length_a                   11.2419(4)
_cell_length_b                   12.3869(5)
_cell_length_c                   13.4125(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1867.72(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9127
_cell_measurement_temperature    170.00
_cell_measurement_theta_max      60.394
_cell_measurement_theta_min      3.421
_shelx_estimated_absorpt_T_max   0.982
_shelx_estimated_absorpt_T_min   0.957
_exptl_absorpt_coefficient_mu    0.443
_exptl_absorpt_correction_T_max  0.7519
_exptl_absorpt_correction_T_min  0.6857
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1322 before and 0.0664 after correction.
The Ratio of minimum to maximum transmission is 0.9120.
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    1.296
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             776
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.04
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0405
_diffrn_reflns_av_unetI/netI     0.0234
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            61419
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         60.660
_diffrn_reflns_theta_min         4.227
_diffrn_ambient_temperature      170.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'zju Bruker D8 Venture'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_source                   ?
_diffrn_source_current           3.57
_diffrn_source_power             0.24957869999999996
_diffrn_source_voltage           69.91
_reflns_Friedel_coverage         0.915
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.997
_reflns_number_gt                4138
_reflns_number_total             4289
_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 (Bruker Nano, Inc., 2019)'
_computing_data_collection       'Bruker Instrument Service vV6.2.14'
_computing_data_reduction        'SAINT V8.40B (Bruker Nano, Inc., 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/2 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.141
_refine_diff_density_min         -0.188
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details 
;
 Flack x determined using 1922 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.01(4)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     254
_refine_ls_number_reflns         4289
_refine_ls_number_restraints     22
_refine_ls_R_factor_all          0.0330
_refine_ls_R_factor_gt           0.0305
_refine_ls_restrained_S_all      1.062
_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)+(0.0474P)²+0.2107P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0776
_refine_ls_wR_factor_ref         0.0790
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
2. Restrained distances
 O1-N1 \\sim O1-N1A
 with sigma of 0.02
 C7-N1 \\sim C7-N1A
 with sigma of 0.02
 C6-N1 \\sim C6-N1A
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
N1 \\sim N1A \\sim C6: within 2A with sigma of 0.01 and sigma for terminal
atoms of 0.02 within 2A
4. Others
 Sof(N1A)=Sof(H7BC)=Sof(H7BD)=1-FVAR(1)
 Sof(N1)=Sof(H7AA)=Sof(H7AB)=FVAR(1)
5.a Secondary CH2 refined with riding coordinates:
 C7(H7AA,H7AB), C7(H7BC,H7BD), C9(H9A,H9B), C11(H11A,H11B), C13(H13A,H13B),
 C14(H14A,H14B), C15(H15A,H15B), C16(H16A,H16B)
5.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C18(H18), C19(H19), C20(H20),
 C21(H21), C22(H22)
;
_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 0.38525(11) 0.34873(10) 0.60511(9) 0.0332(3) Uani 1 1 d D . . . .
N1 N 0.4540(4) 0.3611(4) 0.51586(18) 0.0234(9) Uani 0.605(12) 1 d D U P A 1
N1A N 0.4094(6) 0.4053(5) 0.5169(3) 0.0254(15) Uani 0.395(12) 1 d D U P A 2
C1 C 0.56203(15) 0.49030(14) 0.62086(13) 0.0314(4) Uani 1 1 d . . . . .
H1 H 0.527829 0.459550 0.679074 0.038 Uiso 1 1 calc R U . . .
O2 O 0.15233(11) 0.24191(11) 0.31606(10) 0.0357(3) Uani 1 1 d . . . . .
N2 N 0.30964(12) 0.13330(12) 0.28920(11) 0.0302(3) Uani 1 1 d . . . . .
C2 C 0.65108(16) 0.56722(14) 0.62900(15) 0.0355(4) Uani 1 1 d . . . . .
H2 H 0.677786 0.588479 0.693272 0.043 Uiso 1 1 calc R U . . .
O3 O 0.44252(12) 0.03093(11) 0.13739(10) 0.0392(3) Uani 1 1 d . . . . .
C3 C 0.70183(16) 0.61363(15) 0.54540(16) 0.0377(4) Uani 1 1 d . . . . .
H3 H 0.763210 0.665853 0.552046 0.045 Uiso 1 1 calc R U . . .
C4 C 0.66205(16) 0.58302(14) 0.45203(15) 0.0343(4) Uani 1 1 d . . . . .
H4 H 0.695901 0.615063 0.394267 0.041 Uiso 1 1 calc R U . . .
C5 C 0.57297(15) 0.50580(15) 0.44172(14) 0.0320(4) Uani 1 1 d . . . . .
H5 H 0.546314 0.485473 0.377185 0.038 Uiso 1 1 calc R U . . .
C6 C 0.52274(15) 0.45818(14) 0.52619(14) 0.0317(3) Uani 1 1 d D U . . .
C7 C 0.39281(14) 0.34370(13) 0.42272(12) 0.0261(3) Uani 1 1 d D . . . .
H7AA H 0.450413 0.324313 0.369843 0.031 Uiso 0.605(12) 1 calc R U P A 1
H7AB H 0.350594 0.410240 0.402244 0.031 Uiso 0.605(12) 1 calc R U P A 1
H7BC H 0.470129 0.313724 0.400775 0.031 Uiso 0.395(12) 1 calc R U P A 2
H7BD H 0.363317 0.392669 0.369890 0.031 Uiso 0.395(12) 1 calc R U P A 2
C8 C 0.30374(14) 0.25158(13) 0.43831(12) 0.0229(3) Uani 1 1 d . . . . .
C9 C 0.35079(13) 0.17533(12) 0.52224(12) 0.0241(3) Uani 1 1 d . . . . .
H9A H 0.310556 0.104321 0.525469 0.029 Uiso 1 1 calc R U . . .
H9B H 0.438411 0.167638 0.524182 0.029 Uiso 1 1 calc R U . . .
C10 C 0.30045(13) 0.26077(12) 0.59460(12) 0.0236(3) Uani 1 1 d . . . . .
C11 C 0.20924(13) 0.29065(12) 0.51404(12) 0.0254(3) Uani 1 1 d . . . . .
H11A H 0.190990 0.368716 0.510044 0.031 Uiso 1 1 calc R U . . .
H11B H 0.135762 0.246620 0.515350 0.031 Uiso 1 1 calc R U . . .
C12 C 0.25089(14) 0.20877(13) 0.34203(12) 0.0251(3) Uani 1 1 d . . . . .
C13 C 0.25043(16) 0.07899(16) 0.20568(14) 0.0369(4) Uani 1 1 d . . . . .
H13A H 0.175362 0.116965 0.189583 0.044 Uiso 1 1 calc R U . . .
H13B H 0.230654 0.003901 0.224750 0.044 Uiso 1 1 calc R U . . .
C14 C 0.33017(19) 0.07825(15) 0.11556(13) 0.0380(4) Uani 1 1 d . . . . .
H14A H 0.291326 0.037137 0.061277 0.046 Uiso 1 1 calc R U . . .
H14B H 0.342172 0.153228 0.092064 0.046 Uiso 1 1 calc R U . . .
C15 C 0.50034(16) 0.09332(15) 0.21271(15) 0.0357(4) Uani 1 1 d . . . . .
H15A H 0.509900 0.168534 0.189072 0.043 Uiso 1 1 calc R U . . .
H15B H 0.580567 0.063305 0.225301 0.043 Uiso 1 1 calc R U . . .
C16 C 0.42953(14) 0.09300(14) 0.30895(13) 0.0297(3) Uani 1 1 d . . . . .
H16A H 0.425284 0.018722 0.335975 0.036 Uiso 1 1 calc R U . . .
H16B H 0.469155 0.139444 0.358999 0.036 Uiso 1 1 calc R U . . .
C17 C 0.26207(14) 0.22941(13) 0.69757(12) 0.0252(3) Uani 1 1 d . . . . .
C18 C 0.33076(16) 0.15824(16) 0.75304(14) 0.0337(4) Uani 1 1 d . . . . .
H18 H 0.404011 0.132479 0.726940 0.040 Uiso 1 1 calc R U . . .
C19 C 0.29277(17) 0.12449(17) 0.84669(15) 0.0381(4) Uani 1 1 d . . . . .
H19 H 0.340587 0.076489 0.884703 0.046 Uiso 1 1 calc R U . . .
C20 C 0.18519(17) 0.16079(15) 0.88471(14) 0.0350(4) Uani 1 1 d . . . . .
H20 H 0.158649 0.136798 0.948196 0.042 Uiso 1 1 calc R U . . .
C21 C 0.11684(16) 0.23193(16) 0.82990(14) 0.0356(4) Uani 1 1 d . . . . .
H21 H 0.043481 0.257426 0.856017 0.043 Uiso 1 1 calc R U . . .
C22 C 0.15527(16) 0.26644(15) 0.73626(13) 0.0317(4) Uani 1 1 d . . . . .
H22 H 0.108061 0.315510 0.698882 0.038 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 N1 1.433(3) . ?
O1 N1A 1.402(4) . ?
O1 C10 1.4545(18) . ?
N1 C6 1.436(3) . ?
N1 C7 1.442(3) . ?
N1A C6 1.438(4) . ?
N1A C7 1.487(5) . ?
C1 H1 0.9500 . ?
C1 C2 1.386(2) . ?
C1 C6 1.402(2) . ?
O2 C12 1.232(2) . ?
N2 C12 1.346(2) . ?
N2 C13 1.466(2) . ?
N2 C16 1.461(2) . ?
C2 H2 0.9500 . ?
C2 C3 1.383(3) . ?
O3 C14 1.423(2) . ?
O3 C15 1.428(2) . ?
C3 H3 0.9500 . ?
C3 C4 1.383(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.392(2) . ?
C5 H5 0.9500 . ?
C5 C6 1.397(2) . ?
C7 H7AA 0.9900 . ?
C7 H7AB 0.9900 . ?
C7 H7BC 0.9900 . ?
C7 H7BD 0.9900 . ?
C7 C8 1.532(2) . ?
C8 C9 1.562(2) . ?
C8 C11 1.547(2) . ?
C8 C12 1.517(2) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.543(2) . ?
C10 C11 1.535(2) . ?
C10 C17 1.498(2) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C13 C14 1.505(3) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C15 C16 1.517(3) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 C18 1.388(2) . ?
C17 C22 1.386(2) . ?
C18 H18 0.9500 . ?
C18 C19 1.391(3) . ?
C19 H19 0.9500 . ?
C19 C20 1.387(3) . ?
C20 H20 0.9500 . ?
C20 C21 1.381(3) . ?
C21 H21 0.9500 . ?
C21 C22 1.395(2) . ?
C22 H22 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 O1 C10 110.65(14) . . ?
N1A O1 C10 114.80(17) . . ?
O1 N1 C6 107.4(2) . . ?
O1 N1 C7 116.7(2) . . ?
C6 N1 C7 117.7(2) . . ?
O1 N1A C6 109.0(3) . . ?
O1 N1A C7 115.8(4) . . ?
C6 N1A C7 114.7(4) . . ?
C2 C1 H1 120.2 . . ?
C2 C1 C6 119.59(16) . . ?
C6 C1 H1 120.2 . . ?
C12 N2 C13 119.87(14) . . ?
C12 N2 C16 126.46(14) . . ?
C16 N2 C13 113.60(13) . . ?
C1 C2 H2 119.3 . . ?
C3 C2 C1 121.31(17) . . ?
C3 C2 H2 119.3 . . ?
C14 O3 C15 109.07(13) . . ?
C2 C3 H3 120.4 . . ?
C4 C3 C2 119.13(15) . . ?
C4 C3 H3 120.4 . . ?
C3 C4 H4 119.6 . . ?
C3 C4 C5 120.74(17) . . ?
C5 C4 H4 119.6 . . ?
C4 C5 H5 120.0 . . ?
C4 C5 C6 120.05(17) . . ?
C6 C5 H5 120.0 . . ?
C1 C6 N1 119.64(17) . . ?
C1 C6 N1A 119.2(2) . . ?
C5 C6 N1 119.53(18) . . ?
C5 C6 N1A 118.7(2) . . ?
C5 C6 C1 119.18(15) . . ?
N1 C7 H7AA 110.2 . . ?
N1 C7 H7AB 110.2 . . ?
N1 C7 C8 107.76(15) . . ?
N1A C7 H7BC 109.6 . . ?
N1A C7 H7BD 109.6 . . ?
N1A C7 C8 110.38(18) . . ?
H7AA C7 H7AB 108.5 . . ?
H7BC C7 H7BD 108.1 . . ?
C8 C7 H7AA 110.2 . . ?
C8 C7 H7AB 110.2 . . ?
C8 C7 H7BC 109.6 . . ?
C8 C7 H7BD 109.6 . . ?
C7 C8 C9 109.11(12) . . ?
C7 C8 C11 107.77(12) . . ?
C11 C8 C9 87.05(12) . . ?
C12 C8 C7 113.58(13) . . ?
C12 C8 C9 122.33(13) . . ?
C12 C8 C11 113.53(13) . . ?
C8 C9 H9A 114.5 . . ?
C8 C9 H9B 114.5 . . ?
H9A C9 H9B 111.6 . . ?
C10 C9 C8 85.09(11) . . ?
C10 C9 H9A 114.5 . . ?
C10 C9 H9B 114.5 . . ?
O1 C10 C9 109.53(12) . . ?
O1 C10 C11 108.99(12) . . ?
O1 C10 C17 107.08(12) . . ?
C11 C10 C9 88.14(12) . . ?
C17 C10 C9 120.50(13) . . ?
C17 C10 C11 121.27(13) . . ?
C8 C11 H11A 114.3 . . ?
C8 C11 H11B 114.3 . . ?
C10 C11 C8 85.87(11) . . ?
C10 C11 H11A 114.3 . . ?
C10 C11 H11B 114.3 . . ?
H11A C11 H11B 111.5 . . ?
O2 C12 N2 121.59(15) . . ?
O2 C12 C8 118.46(15) . . ?
N2 C12 C8 119.91(14) . . ?
N2 C13 H13A 109.6 . . ?
N2 C13 H13B 109.6 . . ?
N2 C13 C14 110.25(15) . . ?
H13A C13 H13B 108.1 . . ?
C14 C13 H13A 109.6 . . ?
C14 C13 H13B 109.6 . . ?
O3 C14 C13 111.47(15) . . ?
O3 C14 H14A 109.3 . . ?
O3 C14 H14B 109.3 . . ?
C13 C14 H14A 109.3 . . ?
C13 C14 H14B 109.3 . . ?
H14A C14 H14B 108.0 . . ?
O3 C15 H15A 109.4 . . ?
O3 C15 H15B 109.4 . . ?
O3 C15 C16 111.20(14) . . ?
H15A C15 H15B 108.0 . . ?
C16 C15 H15A 109.4 . . ?
C16 C15 H15B 109.4 . . ?
N2 C16 C15 109.20(15) . . ?
N2 C16 H16A 109.8 . . ?
N2 C16 H16B 109.8 . . ?
C15 C16 H16A 109.8 . . ?
C15 C16 H16B 109.8 . . ?
H16A C16 H16B 108.3 . . ?
C18 C17 C10 119.90(15) . . ?
C22 C17 C10 120.58(15) . . ?
C22 C17 C18 119.43(16) . . ?
C17 C18 H18 119.9 . . ?
C17 C18 C19 120.27(17) . . ?
C19 C18 H18 119.9 . . ?
C18 C19 H19 119.9 . . ?
C20 C19 C18 120.14(18) . . ?
C20 C19 H19 119.9 . . ?
C19 C20 H20 120.1 . . ?
C21 C20 C19 119.75(17) . . ?
C21 C20 H20 120.1 . . ?
C20 C21 H21 119.9 . . ?
C20 C21 C22 120.15(17) . . ?
C22 C21 H21 119.9 . . ?
C17 C22 C21 120.26(17) . . ?
C17 C22 H22 119.9 . . ?
C21 C22 H22 119.9 . . ?

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 N1 C6 C1 31.9(4) . . . . ?
O1 N1 C6 C5 -162.9(2) . . . . ?
O1 N1 C7 C8 -36.6(4) . . . . ?
O1 N1A C6 C1 -29.3(7) . . . . ?
O1 N1A C6 C5 170.4(3) . . . . ?
O1 N1A C7 C8 24.9(6) . . . . ?
O1 C10 C11 C8 82.16(13) . . . . ?
O1 C10 C17 C18 -83.96(18) . . . . ?
O1 C10 C17 C22 99.37(17) . . . . ?
N1 O1 C10 C9 29.5(3) . . . . ?
N1 O1 C10 C11 -65.4(3) . . . . ?
N1 O1 C10 C17 161.7(3) . . . . ?
N1 C7 C8 C9 -27.9(3) . . . . ?
N1 C7 C8 C11 65.2(3) . . . . ?
N1 C7 C8 C12 -168.1(3) . . . . ?
N1A O1 C10 C9 62.2(4) . . . . ?
N1A O1 C10 C11 -32.7(4) . . . . ?
N1A O1 C10 C17 -165.6(4) . . . . ?
N1A C7 C8 C9 -58.9(4) . . . . ?
N1A C7 C8 C11 34.2(4) . . . . ?
N1A C7 C8 C12 160.9(4) . . . . ?
C1 C2 C3 C4 0.5(3) . . . . ?
N2 C13 C14 O3 55.2(2) . . . . ?
C2 C1 C6 N1 164.2(3) . . . . ?
C2 C1 C6 N1A -161.2(4) . . . . ?
C2 C1 C6 C5 -1.0(3) . . . . ?
C2 C3 C4 C5 -0.6(3) . . . . ?
O3 C15 C16 N2 -56.81(19) . . . . ?
C3 C4 C5 C6 -0.1(3) . . . . ?
C4 C5 C6 N1 -164.4(3) . . . . ?
C4 C5 C6 N1A 161.2(4) . . . . ?
C4 C5 C6 C1 0.9(3) . . . . ?
C6 N1 C7 C8 -166.6(3) . . . . ?
C6 N1A C7 C8 153.3(4) . . . . ?
C6 C1 C2 C3 0.4(3) . . . . ?
C7 N1 C6 C1 166.1(3) . . . . ?
C7 N1 C6 C5 -28.6(5) . . . . ?
C7 N1A C6 C1 -161.0(3) . . . . ?
C7 N1A C6 C5 38.7(7) . . . . ?
C7 C8 C9 C10 80.39(13) . . . . ?
C7 C8 C11 C10 -81.58(13) . . . . ?
C7 C8 C12 O2 -97.88(18) . . . . ?
C7 C8 C12 N2 84.60(18) . . . . ?
C8 C9 C10 O1 -81.88(13) . . . . ?
C8 C9 C10 C11 27.63(10) . . . . ?
C8 C9 C10 C17 153.33(14) . . . . ?
C9 C8 C11 C10 27.54(10) . . . . ?
C9 C8 C12 O2 127.78(17) . . . . ?
C9 C8 C12 N2 -49.7(2) . . . . ?
C9 C10 C11 C8 -27.87(10) . . . . ?
C9 C10 C17 C18 42.0(2) . . . . ?
C9 C10 C17 C22 -134.69(16) . . . . ?
C10 O1 N1 C6 171.8(2) . . . . ?
C10 O1 N1 C7 37.0(4) . . . . ?
C10 O1 N1A C6 -157.6(3) . . . . ?
C10 O1 N1A C7 -26.4(7) . . . . ?
C10 C17 C18 C19 -176.77(17) . . . . ?
C10 C17 C22 C21 176.29(16) . . . . ?
C11 C8 C9 C10 -27.41(10) . . . . ?
C11 C8 C12 O2 25.7(2) . . . . ?
C11 C8 C12 N2 -151.80(15) . . . . ?
C11 C10 C17 C18 150.25(16) . . . . ?
C11 C10 C17 C22 -26.4(2) . . . . ?
C12 N2 C13 C14 132.24(17) . . . . ?
C12 N2 C16 C15 -132.00(18) . . . . ?
C12 C8 C9 C10 -143.54(15) . . . . ?
C12 C8 C11 C10 151.71(14) . . . . ?
C13 N2 C12 O2 -7.6(3) . . . . ?
C13 N2 C12 C8 169.88(16) . . . . ?
C13 N2 C16 C15 51.2(2) . . . . ?
C14 O3 C15 C16 62.4(2) . . . . ?
C15 O3 C14 C13 -61.49(19) . . . . ?
C16 N2 C12 O2 175.80(17) . . . . ?
C16 N2 C12 C8 -6.8(3) . . . . ?
C16 N2 C13 C14 -50.7(2) . . . . ?
C17 C10 C11 C8 -152.93(15) . . . . ?
C17 C18 C19 C20 0.8(3) . . . . ?
C18 C17 C22 C21 -0.4(3) . . . . ?
C18 C19 C20 C21 -1.0(3) . . . . ?
C19 C20 C21 C22 0.6(3) . . . . ?
C20 C21 C22 C17 0.1(3) . . . . ?
C22 C17 C18 C19 -0.1(3) . . . . ?


_olex2_submission_special_instructions 'No special instructions were received'
