# Electronic Supplementary Material (ESI) for ChemComm.
# 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_xxq_3aa_1_0m
_database_code_depnum_ccdc_archive 'CCDC 2310615'
loop_
_audit_author_name
_audit_author_address
'Xiangqi Xie'
;East China University Of Science And Technology
China
;
_audit_update_record             
;
2023-11-27 deposited with the CCDC.	2024-01-03 downloaded from the CCDC.
;
_audit_creation_date             2023-10-18
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H23 N O2, 1[C4H8O2]'
_chemical_formula_sum            'C26 H31 N O4'
_chemical_formula_weight         421.52
_chemical_absolute_configuration syn
_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 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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                   7.5575(6)
_cell_length_b                   12.6622(11)
_cell_length_c                   25.9109(19)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2479.5(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1302
_cell_measurement_temperature    295.00
_cell_measurement_theta_max      67.754
_cell_measurement_theta_min      8.684
_shelx_estimated_absorpt_T_max   0.936
_shelx_estimated_absorpt_T_min   0.909
_exptl_absorpt_coefficient_mu    0.604
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.4205
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1601 before and 0.0876 after correction.
The Ratio of minimum to maximum transmission is 0.5584.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.129
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             904
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0533
_diffrn_reflns_av_unetI/netI     0.0618
_diffrn_reflns_Laue_measured_fraction_full 0.974
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            10067
_diffrn_reflns_point_group_measured_fraction_full 0.951
_diffrn_reflns_point_group_measured_fraction_max 0.949
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.254
_diffrn_reflns_theta_min         4.884
_diffrn_ambient_temperature      295.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.974
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_source_current           1.2
_diffrn_source_power             0.06
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.697
_reflns_Friedel_fraction_full    0.921
_reflns_Friedel_fraction_max     0.917
_reflns_number_gt                3869
_reflns_number_total             4305
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _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 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.367
_refine_diff_density_min         -0.318
_refine_diff_density_rms         0.062
_refine_ls_abs_structure_details 
;
 Flack x determined using 1381 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.11(14)
_refine_ls_extinction_coef       0.098(17)
_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   1.264
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     230
_refine_ls_number_reflns         4305
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1003
_refine_ls_R_factor_gt           0.0964
_refine_ls_restrained_S_all      1.264
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2855
_refine_ls_wR_factor_ref         0.2943
_refine_special_details          ?
_olex2_refinement_description    
;
1. 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
2.a Ternary CH refined with riding coordinates:
 C10(H10)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B)
2.c Aromatic/amide H refined with riding coordinates:
 N1(H1), C16(H16), C13(H13), C17(H17), C14(H14), C6(H6), C3(H3), C5(H5), C4(H4)
2.d X=CH2 refined with riding coordinates:
 C18(H18A,H18B)
2.e Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C), C20(H20A,H20B,H20C), C21(H21A,H21B,H21C)
;
_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
O2 O 0.7189(5) 0.2749(2) 0.30133(11) 0.0621(8) Uani 1 1 d . . . . .
N1 N 0.4703(5) 0.3860(3) 0.31587(16) 0.0646(10) Uani 1 1 d . . . . .
H1 H 0.421493 0.395578 0.286252 0.078 Uiso 1 1 calc R U . . .
O1 O 0.2153(5) 0.3892(4) 0.36467(19) 0.0930(13) Uani 1 1 d . . . . .
C8 C 0.6622(6) 0.3721(3) 0.32302(17) 0.0554(9) Uani 1 1 d . . . . .
C16 C 0.7585(7) 0.3455(4) 0.16394(16) 0.0614(11) Uani 1 1 d . . . . .
H16 H 0.763714 0.404861 0.142852 0.074 Uiso 1 1 calc R U . . .
C12 C 0.7351(6) 0.2712(4) 0.24869(15) 0.0543(9) Uani 1 1 d . . . . .
C10 C 0.7333(6) 0.4707(3) 0.24050(18) 0.0595(10) Uani 1 1 d . . . . .
H10 H 0.612768 0.497082 0.235160 0.071 Uiso 1 1 calc R U . . .
C2 C 0.5097(6) 0.3719(4) 0.40270(19) 0.0634(11) Uani 1 1 d . . . . .
C11 C 0.7443(5) 0.3601(3) 0.21732(17) 0.0552(9) Uani 1 1 d . . . . .
C7 C 0.6764(6) 0.3668(3) 0.38015(17) 0.0570(10) Uani 1 1 d . . . . .
C13 C 0.7426(6) 0.1740(4) 0.22675(17) 0.0616(11) Uani 1 1 d . . . . .
H13 H 0.737912 0.115016 0.248110 0.074 Uiso 1 1 calc R U . . .
C9 C 0.7659(7) 0.4641(3) 0.29861(18) 0.0614(10) Uani 1 1 d . . . . .
H9A H 0.730109 0.529890 0.314698 0.074 Uiso 1 1 calc R U . . .
H9B H 0.891282 0.454323 0.304958 0.074 Uiso 1 1 calc R U . . .
C17 C 0.8598(8) 0.5475(4) 0.21532(19) 0.0689(12) Uani 1 1 d . . . . .
H17 H 0.979797 0.531587 0.217013 0.083 Uiso 1 1 calc R U . . .
C15 C 0.7650(7) 0.2479(4) 0.14138(18) 0.0648(11) Uani 1 1 d . . . . .
C14 C 0.7568(7) 0.1584(4) 0.17360(19) 0.0680(12) Uani 1 1 d . . . . .
H14 H 0.760844 0.090664 0.159796 0.082 Uiso 1 1 calc R U . . .
C1 C 0.3798(6) 0.3820(4) 0.3600(2) 0.0644(12) Uani 1 1 d . . . . .
C6 C 0.8277(6) 0.3593(4) 0.41045(19) 0.0683(12) Uani 1 1 d . . . . .
H6 H 0.939569 0.355380 0.395650 0.082 Uiso 1 1 calc R U . . .
C3 C 0.4819(10) 0.3666(5) 0.4551(2) 0.0849(16) Uani 1 1 d . . . . .
H3 H 0.368636 0.366316 0.469094 0.102 Uiso 1 1 calc R U . . .
C22 C 0.7913(14) 0.3361(7) 0.0522(2) 0.115(3) Uani 1 1 d . . . . .
H22A H 0.691100 0.379745 0.060254 0.172 Uiso 1 1 calc R U . . .
H22B H 0.792993 0.321824 0.015800 0.172 Uiso 1 1 calc R U . . .
H22C H 0.898076 0.372160 0.061801 0.172 Uiso 1 1 calc R U . . .
C5 C 0.8049(9) 0.3579(7) 0.4649(2) 0.096(2) Uani 1 1 d . . . . .
H5 H 0.903470 0.354451 0.486333 0.116 Uiso 1 1 calc R U . . .
C18 C 0.8162(11) 0.6326(5) 0.1919(2) 0.0939(19) Uani 1 1 d . . . . .
H18A H 0.697687 0.651537 0.189295 0.113 Uiso 1 1 calc R U . . .
H18B H 0.903075 0.675394 0.177458 0.113 Uiso 1 1 calc R U . . .
C4 C 0.6350(13) 0.3618(6) 0.4866(2) 0.104(2) Uani 1 1 d . . . . .
H4 H 0.622556 0.361100 0.522321 0.124 Uiso 1 1 calc R U . . .
C19 C 0.7776(9) 0.2293(5) 0.08277(18) 0.0807(15) Uani 1 1 d . . . . .
C20 C 0.9399(18) 0.1568(11) 0.0709(3) 0.161(5) Uani 1 1 d . . . . .
H20A H 1.037325 0.176614 0.092666 0.242 Uiso 1 1 calc R U . . .
H20B H 0.973361 0.164700 0.035407 0.242 Uiso 1 1 calc R U . . .
H20C H 0.908875 0.084497 0.077486 0.242 Uiso 1 1 calc R U . . .
C21 C 0.6090(17) 0.1726(9) 0.0642(3) 0.140(4) Uani 1 1 d . . . . .
H21A H 0.611924 0.100204 0.075243 0.210 Uiso 1 1 calc R U . . .
H21B H 0.603072 0.175358 0.027232 0.210 Uiso 1 1 calc R U . . .
H21C H 0.506951 0.206766 0.078603 0.210 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
O2 C8 1.419(5) . ?
O2 C12 1.370(5) . ?
N1 H1 0.8600 . ?
N1 C8 1.472(6) . ?
N1 C1 1.334(6) . ?
O1 C1 1.252(6) . ?
C8 C7 1.486(6) . ?
C8 C9 1.539(6) . ?
C16 H16 0.9300 . ?
C16 C11 1.399(6) . ?
C16 C15 1.369(7) . ?
C12 C11 1.390(6) . ?
C12 C13 1.357(6) . ?
C10 H10 0.9800 . ?
C10 C11 1.527(6) . ?
C10 C9 1.528(6) . ?
C10 C17 1.512(6) . ?
C2 C7 1.389(6) . ?
C2 C1 1.484(8) . ?
C2 C3 1.375(7) . ?
C7 C6 1.390(6) . ?
C13 H13 0.9300 . ?
C13 C14 1.395(6) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C17 H17 0.9300 . ?
C17 C18 1.279(8) . ?
C15 C14 1.408(7) . ?
C15 C19 1.540(6) . ?
C14 H14 0.9300 . ?
C6 H6 0.9300 . ?
C6 C5 1.422(8) . ?
C3 H3 0.9300 . ?
C3 C4 1.418(12) . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C22 C19 1.572(11) . ?
C5 H5 0.9300 . ?
C5 C4 1.402(11) . ?
C18 H18A 0.9300 . ?
C18 H18B 0.9300 . ?
C4 H4 0.9300 . ?
C19 C20 1.563(13) . ?
C19 C21 1.539(11) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 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
C12 O2 C8 116.8(3) . . ?
C8 N1 H1 123.4 . . ?
C1 N1 H1 123.4 . . ?
C1 N1 C8 113.1(4) . . ?
O2 C8 N1 110.5(4) . . ?
O2 C8 C7 109.5(3) . . ?
O2 C8 C9 109.9(3) . . ?
N1 C8 C7 101.6(3) . . ?
N1 C8 C9 111.1(4) . . ?
C7 C8 C9 114.0(3) . . ?
C11 C16 H16 118.5 . . ?
C15 C16 H16 118.5 . . ?
C15 C16 C11 123.0(4) . . ?
O2 C12 C11 124.0(4) . . ?
C13 C12 O2 116.9(4) . . ?
C13 C12 C11 119.2(4) . . ?
C11 C10 H10 107.9 . . ?
C11 C10 C9 109.2(3) . . ?
C9 C10 H10 107.9 . . ?
C17 C10 H10 107.9 . . ?
C17 C10 C11 112.7(4) . . ?
C17 C10 C9 111.0(4) . . ?
C7 C2 C1 106.9(4) . . ?
C3 C2 C7 123.5(5) . . ?
C3 C2 C1 129.6(5) . . ?
C16 C11 C10 120.9(4) . . ?
C12 C11 C16 118.4(4) . . ?
C12 C11 C10 120.7(4) . . ?
C2 C7 C8 110.6(4) . . ?
C2 C7 C6 120.7(4) . . ?
C6 C7 C8 128.7(4) . . ?
C12 C13 H13 118.5 . . ?
C12 C13 C14 123.0(4) . . ?
C14 C13 H13 118.5 . . ?
C8 C9 H9A 109.4 . . ?
C8 C9 H9B 109.4 . . ?
C10 C9 C8 111.4(4) . . ?
C10 C9 H9A 109.4 . . ?
C10 C9 H9B 109.4 . . ?
H9A C9 H9B 108.0 . . ?
C10 C17 H17 117.2 . . ?
C18 C17 C10 125.7(6) . . ?
C18 C17 H17 117.2 . . ?
C16 C15 C14 118.1(4) . . ?
C16 C15 C19 124.2(5) . . ?
C14 C15 C19 117.7(4) . . ?
C13 C14 C15 118.4(4) . . ?
C13 C14 H14 120.8 . . ?
C15 C14 H14 120.8 . . ?
N1 C1 C2 107.6(4) . . ?
O1 C1 N1 126.0(6) . . ?
O1 C1 C2 126.3(5) . . ?
C7 C6 H6 121.2 . . ?
C7 C6 C5 117.5(5) . . ?
C5 C6 H6 121.2 . . ?
C2 C3 H3 121.8 . . ?
C2 C3 C4 116.5(6) . . ?
C4 C3 H3 121.8 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C19 C22 H22A 109.5 . . ?
C19 C22 H22B 109.5 . . ?
C19 C22 H22C 109.5 . . ?
C6 C5 H5 119.7 . . ?
C4 C5 C6 120.5(6) . . ?
C4 C5 H5 119.7 . . ?
C17 C18 H18A 120.0 . . ?
C17 C18 H18B 120.0 . . ?
H18A C18 H18B 120.0 . . ?
C3 C4 H4 119.4 . . ?
C5 C4 C3 121.2(5) . . ?
C5 C4 H4 119.4 . . ?
C15 C19 C22 111.7(5) . . ?
C15 C19 C20 109.4(5) . . ?
C15 C19 C21 109.2(6) . . ?
C20 C19 C22 110.8(7) . . ?
C21 C19 C22 107.4(7) . . ?
C21 C19 C20 108.3(8) . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C19 C21 H21A 109.5 . . ?
C19 C21 H21B 109.5 . . ?
C19 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 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
O2 C8 C7 C2 -114.3(4) . . . . ?
O2 C8 C7 C6 66.6(6) . . . . ?
O2 C8 C9 C10 61.5(5) . . . . ?
O2 C12 C11 C16 -179.2(4) . . . . ?
O2 C12 C11 C10 -1.0(6) . . . . ?
O2 C12 C13 C14 179.2(4) . . . . ?
N1 C8 C7 C2 2.6(5) . . . . ?
N1 C8 C7 C6 -176.5(5) . . . . ?
N1 C8 C9 C10 -61.1(5) . . . . ?
C8 O2 C12 C11 17.1(6) . . . . ?
C8 O2 C12 C13 -162.9(4) . . . . ?
C8 N1 C1 O1 -178.4(5) . . . . ?
C8 N1 C1 C2 3.8(5) . . . . ?
C8 C7 C6 C5 178.6(5) . . . . ?
C16 C15 C14 C13 0.0(7) . . . . ?
C16 C15 C19 C22 2.8(9) . . . . ?
C16 C15 C19 C20 125.8(8) . . . . ?
C16 C15 C19 C21 -115.8(8) . . . . ?
C12 O2 C8 N1 76.8(4) . . . . ?
C12 O2 C8 C7 -172.0(3) . . . . ?
C12 O2 C8 C9 -46.2(5) . . . . ?
C12 C13 C14 C15 0.4(7) . . . . ?
C2 C7 C6 C5 -0.5(7) . . . . ?
C2 C3 C4 C5 -2.7(11) . . . . ?
C11 C16 C15 C14 0.1(8) . . . . ?
C11 C16 C15 C19 179.0(5) . . . . ?
C11 C12 C13 C14 -0.8(7) . . . . ?
C11 C10 C9 C8 -44.8(5) . . . . ?
C11 C10 C17 C18 120.0(6) . . . . ?
C7 C8 C9 C10 -175.2(3) . . . . ?
C7 C2 C1 N1 -1.9(5) . . . . ?
C7 C2 C1 O1 -179.7(5) . . . . ?
C7 C2 C3 C4 3.6(9) . . . . ?
C7 C6 C5 C4 1.3(10) . . . . ?
C13 C12 C11 C16 0.9(6) . . . . ?
C13 C12 C11 C10 179.0(4) . . . . ?
C9 C8 C7 C2 122.2(4) . . . . ?
C9 C8 C7 C6 -56.9(6) . . . . ?
C9 C10 C11 C16 -165.8(4) . . . . ?
C9 C10 C11 C12 16.1(6) . . . . ?
C9 C10 C17 C18 -117.2(6) . . . . ?
C17 C10 C11 C16 -41.9(6) . . . . ?
C17 C10 C11 C12 140.0(4) . . . . ?
C17 C10 C9 C8 -169.6(4) . . . . ?
C15 C16 C11 C12 -0.5(7) . . . . ?
C15 C16 C11 C10 -178.6(4) . . . . ?
C14 C15 C19 C22 -178.3(6) . . . . ?
C14 C15 C19 C20 -55.3(8) . . . . ?
C14 C15 C19 C21 63.1(8) . . . . ?
C1 N1 C8 O2 112.1(4) . . . . ?
C1 N1 C8 C7 -4.0(5) . . . . ?
C1 N1 C8 C9 -125.7(4) . . . . ?
C1 C2 C7 C8 -0.6(5) . . . . ?
C1 C2 C7 C6 178.6(4) . . . . ?
C1 C2 C3 C4 -177.3(6) . . . . ?
C6 C5 C4 C3 0.3(12) . . . . ?
C3 C2 C7 C8 178.7(5) . . . . ?
C3 C2 C7 C6 -2.1(7) . . . . ?
C3 C2 C1 N1 178.8(5) . . . . ?
C3 C2 C1 O1 1.0(9) . . . . ?
C19 C15 C14 C13 -179.0(5) . . . . ?

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 -0.783 0.050 -0.123 200.3 50.0 '1 C4H8O2'
2 -0.604 -0.050 0.377 200.3 50.0 '1 C4H8O2'
3 -0.431 0.450 0.123 200.3 50.1 '1 C4H8O2'
4 0.040 0.550 0.623 200.3 50.0 '1 C4H8O2'

_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_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_xxq_3aa_2_0ma
_database_code_depnum_ccdc_archive 'CCDC 2310616'
loop_
_audit_author_name
_audit_author_address
'Xiangqi Xie'
;East China University Of Science And Technology
China
;
_audit_update_record             
;
2023-11-27 deposited with the CCDC.	2024-01-03 downloaded from the CCDC.
;
_audit_creation_date             2023-10-18
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H23 N O2, 1[C4H8O2]'
_chemical_formula_sum            'C26 H31 N O4'
_chemical_formula_weight         421.52
_chemical_absolute_configuration syn
_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 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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                   8.9352(6)
_cell_length_b                   9.9706(7)
_cell_length_c                   26.0378(18)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2319.7(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9919
_cell_measurement_temperature    295.00
_cell_measurement_theta_max      68.443
_cell_measurement_theta_min      3.395
_shelx_estimated_absorpt_T_max   0.909
_shelx_estimated_absorpt_T_min   0.887
_exptl_absorpt_coefficient_mu    0.646
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.6482
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1122 before and 0.0605 after correction.
The Ratio of minimum to maximum transmission is 0.8607.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.207
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             904
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.15
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0441
_diffrn_reflns_av_unetI/netI     0.0304
_diffrn_reflns_Laue_measured_fraction_full 0.980
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            21429
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.444
_diffrn_reflns_theta_min         7.113
_diffrn_ambient_temperature      295.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_source_current           1.2
_diffrn_source_power             0.06
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.746
_reflns_Friedel_fraction_full    0.990
_reflns_Friedel_fraction_max     0.984
_reflns_number_gt                3983
_reflns_number_total             4181
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _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 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.190
_refine_diff_density_min         -0.181
_refine_diff_density_rms         0.036
_refine_ls_abs_structure_details 
;
 Flack x determined using 1612 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.02(8)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     229
_refine_ls_number_reflns         4181
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0516
_refine_ls_R_factor_gt           0.0502
_refine_ls_restrained_S_all      1.081
_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)+(0.1062P)²+0.2044P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1550
_refine_ls_wR_factor_ref         0.1567
_refine_special_details          ?
_olex2_refinement_description    
;
1. 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
2.a Ternary CH refined with riding coordinates:
 C10(H10)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B)
2.c Aromatic/amide H refined with riding coordinates:
 N1(H1), C16(H16), C14(H14), C17(H17), C6(H6), C13(H13), C5(H5), C4(H4), C3(H3)
2.d X=CH2 refined with riding coordinates:
 C18(H18A,H18B)
2.e Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C), C21(H21A,H21B,H21C), C22(H22A,H22B,H22C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O2 O 0.55409(19) 0.78037(19) 0.63426(7) 0.0511(5) Uani 1 1 d . . . . .
O1 O 0.2640(2) 0.7697(3) 0.49594(8) 0.0743(6) Uani 1 1 d . . . . .
C11 C 0.6280(3) 0.6094(2) 0.69692(10) 0.0431(5) Uani 1 1 d . . . . .
N1 N 0.4510(2) 0.7285(3) 0.55527(8) 0.0569(6) Uani 1 1 d . . . . .
H1 H 0.525880 0.747910 0.535910 0.068 Uiso 1 1 calc R U . . .
C10 C 0.5737(3) 0.4948(2) 0.66306(10) 0.0455(5) Uani 1 1 d . . . . .
H10 H 0.477609 0.462723 0.676446 0.055 Uiso 1 1 calc R U . . .
C16 C 0.6918(3) 0.5849(3) 0.74449(10) 0.0482(6) Uani 1 1 d . . . . .
H16 H 0.698033 0.496478 0.755635 0.058 Uiso 1 1 calc R U . . .
C9 C 0.5493(3) 0.5476(3) 0.60823(10) 0.0510(6) Uani 1 1 d . . . . .
H9A H 0.645666 0.557451 0.591468 0.061 Uiso 1 1 calc R U . . .
H9B H 0.491623 0.482441 0.588921 0.061 Uiso 1 1 calc R U . . .
C15 C 0.7472(3) 0.6849(3) 0.77654(10) 0.0504(6) Uani 1 1 d . . . . .
C7 C 0.3073(3) 0.6789(3) 0.62539(9) 0.0454(5) Uani 1 1 d . . . . .
C12 C 0.6151(3) 0.7423(2) 0.68060(9) 0.0434(5) Uani 1 1 d . . . . .
C14 C 0.7375(3) 0.8162(3) 0.75736(11) 0.0551(6) Uani 1 1 d . . . . .
H14 H 0.777613 0.886244 0.776527 0.066 Uiso 1 1 calc R U . . .
C17 C 0.6823(3) 0.3799(3) 0.66295(12) 0.0589(7) Uani 1 1 d . . . . .
H17 H 0.774308 0.392381 0.646932 0.071 Uiso 1 1 calc R U . . .
C2 C 0.2140(3) 0.7097(3) 0.58465(10) 0.0481(6) Uani 1 1 d . . . . .
C6 C 0.2483(3) 0.6552(3) 0.67418(10) 0.0515(6) Uani 1 1 d . . . . .
H6 H 0.310072 0.636795 0.702050 0.062 Uiso 1 1 calc R U . . .
C8 C 0.4685(3) 0.6811(3) 0.60733(9) 0.0474(6) Uani 1 1 d . . . . .
C13 C 0.6708(3) 0.8442(3) 0.71131(11) 0.0523(6) Uani 1 1 d . . . . .
H13 H 0.662750 0.932754 0.700464 0.063 Uiso 1 1 calc R U . . .
C5 C 0.0934(3) 0.6602(4) 0.67949(12) 0.0645(8) Uani 1 1 d . . . . .
H5 H 0.050511 0.643544 0.711393 0.077 Uiso 1 1 calc R U . . .
C19 C 0.8155(4) 0.6509(3) 0.82874(12) 0.0644(8) Uani 1 1 d . . . . .
C4 C 0.0028(3) 0.6895(4) 0.63823(13) 0.0695(9) Uani 1 1 d . . . . .
H4 H -0.100337 0.691543 0.642876 0.083 Uiso 1 1 calc R U . . .
C18 C 0.6549(5) 0.2609(3) 0.68443(16) 0.0807(10) Uani 1 1 d . . . . .
H18A H 0.563914 0.245308 0.700722 0.097 Uiso 1 1 calc R U . . .
H18B H 0.726751 0.193465 0.683100 0.097 Uiso 1 1 calc R U . . .
C3 C 0.0605(3) 0.7157(3) 0.59051(11) 0.0623(7) Uani 1 1 d . . . . .
H3 H -0.001637 0.736716 0.563005 0.075 Uiso 1 1 calc R U . . .
C1 C 0.3062(3) 0.7400(3) 0.53920(10) 0.0545(6) Uani 1 1 d . . . . .
C20 C 0.7031(6) 0.5709(7) 0.86036(16) 0.1175(19) Uani 1 1 d . . . . .
H20A H 0.616560 0.625202 0.867024 0.176 Uiso 1 1 calc R U . . .
H20B H 0.748148 0.544889 0.892325 0.176 Uiso 1 1 calc R U . . .
H20C H 0.673849 0.492174 0.841655 0.176 Uiso 1 1 calc R U . . .
C21 C 0.9465(6) 0.5535(6) 0.82051(18) 0.1175(18) Uani 1 1 d . . . . .
H21A H 0.916461 0.483744 0.797263 0.176 Uiso 1 1 calc R U . . .
H21B H 0.974695 0.514571 0.852817 0.176 Uiso 1 1 calc R U . . .
H21C H 1.030105 0.601182 0.806304 0.176 Uiso 1 1 calc R U . . .
C22 C 0.8762(10) 0.7689(6) 0.8553(2) 0.160(3) Uani 1 1 d . . . . .
H22A H 0.937866 0.819179 0.832026 0.241 Uiso 1 1 calc R U . . .
H22B H 0.935052 0.740444 0.884132 0.241 Uiso 1 1 calc R U . . .
H22C H 0.795256 0.824317 0.867042 0.241 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
O2 C12 1.377(3) . ?
O2 C8 1.434(3) . ?
O1 C1 1.224(3) . ?
C11 C10 1.523(4) . ?
C11 C16 1.385(4) . ?
C11 C12 1.396(3) . ?
N1 H1 0.8600 . ?
N1 C8 1.444(3) . ?
N1 C1 1.364(3) . ?
C10 H10 0.9800 . ?
C10 C9 1.537(4) . ?
C10 C17 1.502(4) . ?
C16 H16 0.9300 . ?
C16 C15 1.391(4) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 C8 1.515(4) . ?
C15 C14 1.405(4) . ?
C15 C19 1.528(4) . ?
C7 C2 1.384(4) . ?
C7 C6 1.395(3) . ?
C7 C8 1.516(3) . ?
C12 C13 1.386(4) . ?
C14 H14 0.9300 . ?
C14 C13 1.368(4) . ?
C17 H17 0.9300 . ?
C17 C18 1.334(5) . ?
C2 C3 1.381(4) . ?
C2 C1 1.473(4) . ?
C6 H6 0.9300 . ?
C6 C5 1.392(4) . ?
C13 H13 0.9300 . ?
C5 H5 0.9300 . ?
C5 C4 1.376(5) . ?
C19 C20 1.524(6) . ?
C19 C21 1.536(6) . ?
C19 C22 1.468(6) . ?
C4 H4 0.9300 . ?
C4 C3 1.370(4) . ?
C18 H18A 0.9300 . ?
C18 H18B 0.9300 . ?
C3 H3 0.9300 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C12 O2 C8 116.69(19) . . ?
C16 C11 C10 121.1(2) . . ?
C16 C11 C12 118.3(2) . . ?
C12 C11 C10 120.6(2) . . ?
C8 N1 H1 122.6 . . ?
C1 N1 H1 122.6 . . ?
C1 N1 C8 114.7(2) . . ?
C11 C10 H10 108.5 . . ?
C11 C10 C9 109.0(2) . . ?
C9 C10 H10 108.5 . . ?
C17 C10 C11 111.6(2) . . ?
C17 C10 H10 108.5 . . ?
C17 C10 C9 110.5(2) . . ?
C11 C16 H16 118.1 . . ?
C11 C16 C15 123.8(2) . . ?
C15 C16 H16 118.1 . . ?
C10 C9 H9A 109.1 . . ?
C10 C9 H9B 109.1 . . ?
H9A C9 H9B 107.8 . . ?
C8 C9 C10 112.5(2) . . ?
C8 C9 H9A 109.1 . . ?
C8 C9 H9B 109.1 . . ?
C16 C15 C14 115.6(2) . . ?
C16 C15 C19 121.1(3) . . ?
C14 C15 C19 123.2(3) . . ?
C2 C7 C6 120.5(2) . . ?
C2 C7 C8 109.4(2) . . ?
C6 C7 C8 130.1(2) . . ?
O2 C12 C11 124.1(2) . . ?
O2 C12 C13 116.4(2) . . ?
C13 C12 C11 119.4(2) . . ?
C15 C14 H14 119.0 . . ?
C13 C14 C15 121.9(2) . . ?
C13 C14 H14 119.0 . . ?
C10 C17 H17 118.0 . . ?
C18 C17 C10 124.0(3) . . ?
C18 C17 H17 118.0 . . ?
C7 C2 C1 108.9(2) . . ?
C3 C2 C7 121.5(2) . . ?
C3 C2 C1 129.4(2) . . ?
C7 C6 H6 121.3 . . ?
C5 C6 C7 117.4(3) . . ?
C5 C6 H6 121.3 . . ?
O2 C8 N1 106.9(2) . . ?
O2 C8 C9 110.16(19) . . ?
O2 C8 C7 111.4(2) . . ?
N1 C8 C9 110.7(2) . . ?
N1 C8 C7 101.13(19) . . ?
C9 C8 C7 115.8(2) . . ?
C12 C13 H13 119.6 . . ?
C14 C13 C12 120.9(2) . . ?
C14 C13 H13 119.6 . . ?
C6 C5 H5 119.5 . . ?
C4 C5 C6 121.0(3) . . ?
C4 C5 H5 119.5 . . ?
C15 C19 C21 108.7(3) . . ?
C20 C19 C15 109.4(3) . . ?
C20 C19 C21 104.3(4) . . ?
C22 C19 C15 112.9(3) . . ?
C22 C19 C20 114.1(5) . . ?
C22 C19 C21 107.0(5) . . ?
C5 C4 H4 119.1 . . ?
C3 C4 C5 121.8(3) . . ?
C3 C4 H4 119.1 . . ?
C17 C18 H18A 120.0 . . ?
C17 C18 H18B 120.0 . . ?
H18A C18 H18B 120.0 . . ?
C2 C3 H3 121.1 . . ?
C4 C3 C2 117.7(3) . . ?
C4 C3 H3 121.1 . . ?
O1 C1 N1 126.5(3) . . ?
O1 C1 C2 128.1(2) . . ?
N1 C1 C2 105.5(2) . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C19 C21 H21A 109.5 . . ?
C19 C21 H21B 109.5 . . ?
C19 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C19 C22 H22A 109.5 . . ?
C19 C22 H22B 109.5 . . ?
C19 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 C12 C13 C14 -178.1(2) . . . . ?
C11 C10 C9 C8 -44.5(3) . . . . ?
C11 C10 C17 C18 111.1(3) . . . . ?
C11 C16 C15 C14 -1.2(4) . . . . ?
C11 C16 C15 C19 179.7(2) . . . . ?
C11 C12 C13 C14 -0.3(4) . . . . ?
C10 C11 C16 C15 178.2(2) . . . . ?
C10 C11 C12 O2 0.1(4) . . . . ?
C10 C11 C12 C13 -177.5(2) . . . . ?
C10 C9 C8 O2 60.6(3) . . . . ?
C10 C9 C8 N1 178.7(2) . . . . ?
C10 C9 C8 C7 -67.0(3) . . . . ?
C16 C11 C10 C9 -164.7(2) . . . . ?
C16 C11 C10 C17 -42.3(3) . . . . ?
C16 C11 C12 O2 179.9(2) . . . . ?
C16 C11 C12 C13 2.3(4) . . . . ?
C16 C15 C14 C13 3.3(4) . . . . ?
C16 C15 C19 C20 -55.5(4) . . . . ?
C16 C15 C19 C21 57.8(4) . . . . ?
C16 C15 C19 C22 176.3(5) . . . . ?
C9 C10 C17 C18 -127.4(3) . . . . ?
C15 C14 C13 C12 -2.6(4) . . . . ?
C7 C2 C3 C4 -0.2(5) . . . . ?
C7 C2 C1 O1 178.9(3) . . . . ?
C7 C2 C1 N1 -1.2(3) . . . . ?
C7 C6 C5 C4 -1.0(5) . . . . ?
C12 O2 C8 N1 -164.76(19) . . . . ?
C12 O2 C8 C9 -44.4(3) . . . . ?
C12 O2 C8 C7 85.6(3) . . . . ?
C12 C11 C10 C9 15.1(3) . . . . ?
C12 C11 C10 C17 137.5(3) . . . . ?
C12 C11 C16 C15 -1.6(4) . . . . ?
C14 C15 C19 C20 125.4(4) . . . . ?
C14 C15 C19 C21 -121.3(4) . . . . ?
C14 C15 C19 C22 -2.8(6) . . . . ?
C17 C10 C9 C8 -167.5(2) . . . . ?
C2 C7 C6 C5 1.8(4) . . . . ?
C2 C7 C8 O2 118.7(2) . . . . ?
C2 C7 C8 N1 5.4(3) . . . . ?
C2 C7 C8 C9 -114.3(2) . . . . ?
C6 C7 C2 C3 -1.2(4) . . . . ?
C6 C7 C2 C1 175.6(3) . . . . ?
C6 C7 C8 O2 -59.4(4) . . . . ?
C6 C7 C8 N1 -172.7(3) . . . . ?
C6 C7 C8 C9 67.6(4) . . . . ?
C6 C5 C4 C3 -0.4(6) . . . . ?
C8 O2 C12 C11 15.1(3) . . . . ?
C8 O2 C12 C13 -167.2(2) . . . . ?
C8 N1 C1 O1 -175.0(3) . . . . ?
C8 N1 C1 C2 5.1(3) . . . . ?
C8 C7 C2 C3 -179.5(3) . . . . ?
C8 C7 C2 C1 -2.8(3) . . . . ?
C8 C7 C6 C5 179.7(3) . . . . ?
C5 C4 C3 C2 1.0(5) . . . . ?
C19 C15 C14 C13 -177.6(3) . . . . ?
C3 C2 C1 O1 -4.6(6) . . . . ?
C3 C2 C1 N1 175.2(3) . . . . ?
C1 N1 C8 O2 -123.2(3) . . . . ?
C1 N1 C8 C9 116.8(3) . . . . ?
C1 N1 C8 C7 -6.5(3) . . . . ?
C1 C2 C3 C4 -176.2(3) . . . . ?

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 -0.615 -0.250 0.000 340.2 88.9 '2 C4H8O2'
2 -0.028 0.250 0.500 340.2 88.9 '2 C4H8O2'

_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_olex2_submission_special_instructions 'No special instructions were received'
