# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_wangmei1223
_database_code_depnum_ccdc_archive 'CCDC 1045102'
_audit_update_record             
;
2015-03-30 deposited with the CCDC.	2023-03-01 downloaded from the CCDC.
;
_audit_creation_date             2014-12-24
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.12.23 svn.r3114 for OlexSys, GUI svn.r4973)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C24 H25 N O5'
_chemical_formula_sum            'C24 H25 N O5'
_chemical_formula_weight         407.45
_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 0.0181 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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z'

_cell_length_a                   7.14183(12)
_cell_length_b                   7.64267(12)
_cell_length_c                   20.2119(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 93.1825(15)
_cell_angle_gamma                90.00
_cell_volume                     1101.52(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3865
_cell_measurement_temperature    290.92(10)
_cell_measurement_theta_max      69.6340
_cell_measurement_theta_min      7.8010
_exptl_absorpt_coefficient_mu    0.702
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.57327
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_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    1.228
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             432
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.263
_exptl_crystal_size_min          0.22
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0126
_diffrn_reflns_av_unetI/netI     0.0173
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            7064
_diffrn_reflns_theta_full        69.66
_diffrn_reflns_theta_max         69.66
_diffrn_reflns_theta_min         6.19
_diffrn_ambient_temperature      290.92(10)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega    7.00   34.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   57.0000  150.0000 27

#__ type_ start__ end____ width___ exp.time_
  2 omega  -73.00  -23.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -19.0000   90.0000 50

#__ type_ start__ end____ width___ exp.time_
  3 omega  -12.00   47.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -19.0000   90.0000 59

#__ type_ start__ end____ width___ exp.time_
  4 omega  -17.00   57.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -77.0000  120.0000 74

#__ type_ start__ end____ width___ exp.time_
  5 omega   53.00  122.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   57.0000 -120.0000 69

#__ type_ start__ end____ width___ exp.time_
  6 omega    1.00   65.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -57.0000    0.0000 64

#__ type_ start__ end____ width___ exp.time_
  7 omega   34.00  123.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   57.0000 -180.0000 89

#__ type_ start__ end____ width___ exp.time_
  8 omega   29.00  113.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   77.0000   90.0000 84

#__ type_ start__ end____ width___ exp.time_
  9 omega  -11.00   45.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -57.0000  -60.0000 56

#__ type_ start__ end____ width___ exp.time_
 10 omega   47.00  118.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -91.0000 -150.0000 71

#__ type_ start__ end____ width___ exp.time_
 11 omega   35.00   67.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000  -60.0000 32

#__ type_ start__ end____ width___ exp.time_
 12 omega   52.00  129.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -63.0000  -30.0000 77

#__ type_ start__ end____ width___ exp.time_
 13 omega   39.00  103.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -50.0000 -150.0000 64

#__ type_ start__ end____ width___ exp.time_
 14 omega   40.00   82.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000  -30.0000 42

#__ type_ start__ end____ width___ exp.time_
 15 omega  125.00  173.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000 -120.0000 48

#__ type_ start__ end____ width___ exp.time_
 16 omega   51.00   88.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000  120.0000 37

#__ type_ start__ end____ width___ exp.time_
 17 omega   36.00   85.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000   90.0000 49

#__ type_ start__ end____ width___ exp.time_
 18 omega   35.00  106.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000    0.0000 71

#__ type_ start__ end____ width___ exp.time_
 19 omega   81.00  178.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   38.0000  -90.0000 97

#__ type_ start__ end____ width___ exp.time_
 20 omega   37.00  114.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000 -180.0000 77

#__ type_ start__ end____ width___ exp.time_
 21 omega  111.00  173.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   63.0000 -150.0000 62

#__ type_ start__ end____ width___ exp.time_
 22 omega   77.00  108.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000   90.0000 31

#__ type_ start__ end____ width___ exp.time_
 23 omega   42.00  178.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -12.0000 -150.0000 136
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.1603034000
_diffrn_orient_matrix_UB_12      -0.0379823000
_diffrn_orient_matrix_UB_13      0.0522311000
_diffrn_orient_matrix_UB_21      -0.0138068000
_diffrn_orient_matrix_UB_22      0.1885394000
_diffrn_orient_matrix_UB_23      0.0262729000
_diffrn_orient_matrix_UB_31      -0.1441766000
_diffrn_orient_matrix_UB_32      -0.0603444000
_diffrn_orient_matrix_UB_33      0.0490914000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                3891
_reflns_number_total             4053
_reflns_odcompleteness_completeness 99.63
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.089
_refine_diff_density_min         -0.124
_refine_diff_density_rms         0.027
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.02(16)
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     316
_refine_ls_number_reflns         4053
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0321
_refine_ls_R_factor_gt           0.0309
_refine_ls_restrained_S_all      1.045
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0510P)²+0.0375P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0826
_refine_ls_wR_factor_ref         0.0841
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_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. Others
 Fixed Sof: O4(0.47) O5(0.47) C10(0.47) C11(0.47) H11A(0.47) H11B(0.47)
 H11C(0.47) O4'(0.53) O5'(0.53) C10'(0.53) C11'(0.53) H11D(0.53) H11E(0.53)
 H11F(0.53)
3.a Ternary CH refined with riding coordinates:
 C21(H21)
3.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B)
3.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C4(H4), C5(H5), C14(H14), C15(H15), C16(H16), C17(H17),
 C18(H18)
3.d Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C), C23(H23A,H23B,H23C), C24(H24A,H24B,H24C), C11(H11A,H11B,
 H11C), C11'(H11D,H11E,H11F)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
O1 O 0.83783(14) 0.2668(2) 0.33111(6) 0.0775(4) Uani 1 d . . .
O2 O 0.57927(12) 0.77664(12) 0.20784(5) 0.0528(2) Uani 1 d . . .
O3 O 0.59884(17) 1.06967(16) 0.20798(7) 0.0822(4) Uani 1 d . . .
N1 N 0.84841(15) 0.72265(14) 0.15035(6) 0.0506(2) Uani 1 d . . .
C1 C 0.5969(2) 0.0905(2) 0.41222(9) 0.0705(4) Uani 1 d . . .
H1 H 0.7205 0.0521 0.4124 0.085 Uiso 1 calc . . R
C2 C 0.4765(3) 0.0165(3) 0.45521(9) 0.0771(5) Uani 1 d . . .
H2 H 0.5202 -0.0713 0.4840 0.093 Uiso 1 calc . . R
C3 C 0.2922(2) 0.0702(2) 0.45641(7) 0.0646(4) Uani 1 d . . .
C4 C 0.2309(2) 0.1986(2) 0.41222(7) 0.0635(4) Uani 1 d . . .
H4 H 0.1070 0.2361 0.4119 0.076 Uiso 1 calc . . R
C5 C 0.34968(19) 0.2721(2) 0.36856(7) 0.0565(3) Uani 1 d . . .
H5 H 0.3043 0.3566 0.3387 0.068 Uiso 1 calc . . R
C6 C 0.53561(18) 0.22182(18) 0.36862(6) 0.0502(3) Uani 1 d . . .
C7 C 0.67286(19) 0.30490(19) 0.32577(6) 0.0526(3) Uani 1 d . . .
C8 C 0.60570(18) 0.44116(18) 0.27586(6) 0.0501(3) Uani 1 d . . .
H8A H 0.5440 0.5348 0.2987 0.060 Uiso 1 calc . . R
H8B H 0.5141 0.3887 0.2447 0.060 Uiso 1 calc . . R
C9 C 0.76463(19) 0.5175(2) 0.23805(8) 0.0572(3) Uani 1 d . . .
H9 H 0.830(3) 0.426(3) 0.2168(10) 0.073(5) Uiso 1 d . . .
C12 C 0.69079(18) 0.63804(16) 0.18079(6) 0.0473(3) Uani 1 d . . .
C13 C 0.57174(18) 0.54005(16) 0.12856(6) 0.0470(3) Uani 1 d . . .
C14 C 0.6572(2) 0.4414(2) 0.08133(8) 0.0629(3) Uani 1 d . . .
H14 H 0.7874 0.4363 0.0818 0.076 Uiso 1 calc . . R
C15 C 0.5509(3) 0.3502(2) 0.03350(9) 0.0747(5) Uani 1 d . . .
H15 H 0.6102 0.2833 0.0024 0.090 Uiso 1 calc A . R
C16 C 0.3598(3) 0.3579(2) 0.03156(8) 0.0738(4) Uani 1 d . . .
H16 H 0.2887 0.2982 -0.0011 0.089 Uiso 1 calc . . R
C17 C 0.2732(2) 0.4547(3) 0.07837(9) 0.0707(4) Uani 1 d . . .
H17 H 0.1430 0.4596 0.0774 0.085 Uiso 1 calc A . R
C18 C 0.37788(19) 0.5451(2) 0.12704(7) 0.0556(3) Uani 1 d . . .
H18 H 0.3177 0.6093 0.1587 0.067 Uiso 1 calc . . R
C19 C 0.66169(19) 0.93052(19) 0.19460(7) 0.0559(3) Uani 1 d . . .
C20 C 0.83448(19) 0.88635(18) 0.15907(7) 0.0523(3) Uani 1 d . . .
C21 C 0.9686(2) 1.0232(2) 0.13817(9) 0.0646(4) Uani 1 d . . .
H21 H 0.8954 1.1233 0.1209 0.078 Uiso 1 calc . . R
C22 C 1.0901(3) 0.9588(3) 0.08370(11) 0.0903(6) Uani 1 d . . .
H22A H 1.1581 0.8566 0.0987 0.135 Uiso 1 calc . . GR
H22B H 1.1770 1.0489 0.0730 0.135 Uiso 1 calc . . GR
H22C H 1.0120 0.9302 0.0450 0.135 Uiso 1 calc . . GR
C23 C 1.0884(3) 1.0844(3) 0.19817(12) 0.0923(6) Uani 1 d . . .
H23A H 1.0089 1.1160 0.2330 0.138 Uiso 1 calc . . GR
H23B H 1.1611 1.1841 0.1863 0.138 Uiso 1 calc . . GR
H23C H 1.1710 0.9916 0.2131 0.138 Uiso 1 calc . . GR
C24 C 0.1609(3) -0.0072(4) 0.50452(11) 0.0980(7) Uani 1 d . . .
H24A H 0.1807 0.0487 0.5469 0.147 Uiso 1 calc . . GR
H24B H 0.1848 -0.1304 0.5091 0.147 Uiso 1 calc . . GR
H24C H 0.0335 0.0107 0.4882 0.147 Uiso 1 calc . . GR
O4 O 1.0954(3) 0.5448(5) 0.25786(15) 0.0805(8) Uani 0.47 d A 1 .
O5 O 0.8834(10) 0.6906(7) 0.3147(3) 0.0826(16) Uani 0.47 d A 1 .
C10 C 0.9363(7) 0.5772(6) 0.2693(2) 0.0591(8) Uani 0.47 d A 1 .
C11 C 1.0479(9) 0.7775(10) 0.3505(3) 0.1178(19) Uani 0.47 d A 1 .
H11A H 1.1308 0.8226 0.3188 0.177 Uiso 0.47 calc A 1 GR
H11B H 1.1136 0.6938 0.3785 0.177 Uiso 0.47 calc A 1 GR
H11C H 1.0044 0.8718 0.3770 0.177 Uiso 0.47 calc A 1 GR
O4' O 0.8109(5) 0.7178(5) 0.33862(17) 0.0825(9) Uani 0.53 d A 2 .
O5' O 1.0598(3) 0.6410(3) 0.28287(11) 0.0652(5) Uani 0.53 d A 2 .
C10' C 0.8785(8) 0.6400(6) 0.2940(2) 0.0487(8) Uani 0.53 d A 2 .
C11' C 1.1784(5) 0.7428(6) 0.3273(2) 0.0833(10) Uani 0.53 d A 2 .
H11D H 1.2995 0.7553 0.3095 0.125 Uiso 0.53 calc A 2 GR
H11E H 1.1915 0.6850 0.3695 0.125 Uiso 0.53 calc A 2 GR
H11F H 1.1237 0.8562 0.3328 0.125 Uiso 0.53 calc A 2 GR


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C7 1.2126(17) . ?
O2 C12 1.4504(15) . ?
O2 C19 1.3486(18) . ?
O3 C19 1.1912(19) . ?
N1 C12 1.4631(16) . ?
N1 C20 1.2681(18) . ?
C1 H1 0.9300 . ?
C1 C2 1.377(2) . ?
C1 C6 1.390(2) . ?
C2 H2 0.9300 . ?
C2 C3 1.380(2) . ?
C3 C4 1.381(2) . ?
C3 C24 1.509(2) . ?
C4 H4 0.9300 . ?
C4 C5 1.377(2) . ?
C5 H5 0.9300 . ?
C5 C6 1.3824(19) . ?
C6 C7 1.4861(19) . ?
C7 C8 1.5094(18) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 C9 1.5196(18) . ?
C9 H9 0.96(2) . ?
C9 C12 1.5487(18) . ?
C9 C10 1.423(4) . ?
C9 C10' 1.647(5) . ?
C12 C13 1.5160(19) . ?
C13 C14 1.3848(19) . ?
C13 C18 1.3837(19) . ?
C14 H14 0.9300 . ?
C14 C15 1.383(3) . ?
C15 H15 0.9300 . ?
C15 C16 1.365(3) . ?
C16 H16 0.9300 . ?
C16 C17 1.375(3) . ?
C17 H17 0.9300 . ?
C17 C18 1.386(2) . ?
C18 H18 0.9300 . ?
C19 C20 1.500(2) . ?
C20 C21 1.4948(19) . ?
C21 H21 0.9800 . ?
C21 C22 1.521(3) . ?
C21 C23 1.519(3) . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
O4 C10 1.197(6) . ?
O5 C10 1.332(6) . ?
O5 C11 1.500(7) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
O4' C10' 1.204(7) . ?
O5' C10' 1.326(6) . ?
O5' C11' 1.430(4) . ?
C11' H11D 0.9600 . ?
C11' H11E 0.9600 . ?
C11' H11F 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
C19 O2 C12 107.89(10) . . ?
C20 N1 C12 108.03(11) . . ?
C2 C1 H1 119.6 . . ?
C2 C1 C6 120.72(15) . . ?
C6 C1 H1 119.6 . . ?
C1 C2 H2 119.4 . . ?
C1 C2 C3 121.22(14) . . ?
C3 C2 H2 119.4 . . ?
C2 C3 C4 117.92(14) . . ?
C2 C3 C24 121.48(15) . . ?
C4 C3 C24 120.61(16) . . ?
C3 C4 H4 119.3 . . ?
C5 C4 C3 121.31(14) . . ?
C5 C4 H4 119.3 . . ?
C4 C5 H5 119.6 . . ?
C4 C5 C6 120.77(13) . . ?
C6 C5 H5 119.6 . . ?
C1 C6 C7 118.91(12) . . ?
C5 C6 C1 118.02(13) . . ?
C5 C6 C7 123.05(12) . . ?
O1 C7 C6 120.97(12) . . ?
O1 C7 C8 119.75(13) . . ?
C6 C7 C8 119.26(11) . . ?
C7 C8 H8A 109.1 . . ?
C7 C8 H8B 109.1 . . ?
C7 C8 C9 112.49(11) . . ?
H8A C8 H8B 107.8 . . ?
C9 C8 H8A 109.1 . . ?
C9 C8 H8B 109.1 . . ?
C8 C9 H9 110.0(12) . . ?
C8 C9 C12 111.80(11) . . ?
C8 C9 C10' 103.1(2) . . ?
C12 C9 H9 104.8(12) . . ?
C12 C9 C10' 108.02(17) . . ?
C10 C9 C8 123.3(2) . . ?
C10 C9 H9 90.2(12) . . ?
C10 C9 C12 112.98(17) . . ?
C10 C9 C10' 29.8(3) . . ?
C10' C9 H9 119.3(12) . . ?
O2 C12 N1 106.69(10) . . ?
O2 C12 C9 108.91(11) . . ?
O2 C12 C13 108.95(10) . . ?
N1 C12 C9 109.83(10) . . ?
N1 C12 C13 109.90(10) . . ?
C13 C12 C9 112.40(11) . . ?
C14 C13 C12 119.84(12) . . ?
C18 C13 C12 121.56(11) . . ?
C18 C13 C14 118.60(13) . . ?
C13 C14 H14 119.7 . . ?
C15 C14 C13 120.69(15) . . ?
C15 C14 H14 119.7 . . ?
C14 C15 H15 119.8 . . ?
C16 C15 C14 120.49(15) . . ?
C16 C15 H15 119.8 . . ?
C15 C16 H16 120.3 . . ?
C15 C16 C17 119.37(15) . . ?
C17 C16 H16 120.3 . . ?
C16 C17 H17 119.6 . . ?
C16 C17 C18 120.77(16) . . ?
C18 C17 H17 119.6 . . ?
C13 C18 C17 120.07(13) . . ?
C13 C18 H18 120.0 . . ?
C17 C18 H18 120.0 . . ?
O2 C19 C20 106.16(11) . . ?
O3 C19 O2 124.01(13) . . ?
O3 C19 C20 129.78(14) . . ?
N1 C20 C19 111.19(12) . . ?
N1 C20 C21 126.48(13) . . ?
C21 C20 C19 122.32(13) . . ?
C20 C21 H21 108.0 . . ?
C20 C21 C22 112.24(14) . . ?
C20 C21 C23 109.34(14) . . ?
C22 C21 H21 108.0 . . ?
C23 C21 H21 108.0 . . ?
C23 C21 C22 111.00(15) . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C21 C23 H23A 109.5 . . ?
C21 C23 H23B 109.5 . . ?
C21 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C3 C24 H24A 109.5 . . ?
C3 C24 H24B 109.5 . . ?
C3 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C10 O5 C11 112.1(6) . . ?
O4 C10 C9 130.6(5) . . ?
O4 C10 O5 125.2(5) . . ?
O5 C10 C9 104.1(4) . . ?
C10' O5' C11' 116.5(3) . . ?
O4' C10' C9 126.3(4) . . ?
O4' C10' O5' 124.0(4) . . ?
O5' C10' C9 109.7(4) . . ?
O5' C11' H11D 109.5 . . ?
O5' C11' H11E 109.5 . . ?
O5' C11' H11F 109.5 . . ?
H11D C11' H11E 109.5 . . ?
H11D C11' H11F 109.5 . . ?
H11E C11' H11F 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C7 C8 C9 -1.0(2) . . . . ?
O2 C12 C13 C14 159.48(12) . . . . ?
O2 C12 C13 C18 -21.11(16) . . . . ?
O2 C19 C20 N1 2.04(16) . . . . ?
O2 C19 C20 C21 -177.63(13) . . . . ?
O3 C19 C20 N1 -175.64(17) . . . . ?
O3 C19 C20 C21 4.7(2) . . . . ?
N1 C12 C13 C14 42.92(16) . . . . ?
N1 C12 C13 C18 -137.67(12) . . . . ?
N1 C20 C21 C22 20.5(2) . . . . ?
N1 C20 C21 C23 -103.1(2) . . . . ?
C1 C2 C3 C4 1.2(3) . . . . ?
C1 C2 C3 C24 -178.5(2) . . . . ?
C1 C6 C7 O1 -4.2(2) . . . . ?
C1 C6 C7 C8 176.94(14) . . . . ?
C2 C1 C6 C5 -1.7(3) . . . . ?
C2 C1 C6 C7 176.59(17) . . . . ?
C2 C3 C4 C5 -0.5(3) . . . . ?
C3 C4 C5 C6 -1.3(3) . . . . ?
C4 C5 C6 C1 2.4(2) . . . . ?
C4 C5 C6 C7 -175.85(14) . . . . ?
C5 C6 C7 O1 173.97(15) . . . . ?
C5 C6 C7 C8 -4.8(2) . . . . ?
C6 C1 C2 C3 -0.1(3) . . . . ?
C6 C7 C8 C9 177.86(12) . . . . ?
C7 C8 C9 C12 172.30(11) . . . . ?
C7 C8 C9 C10 -47.7(3) . . . . ?
C7 C8 C9 C10' -71.9(2) . . . . ?
C8 C9 C12 O2 57.60(15) . . . . ?
C8 C9 C12 N1 174.10(11) . . . . ?
C8 C9 C12 C13 -63.22(16) . . . . ?
C8 C9 C10 O4 129.5(4) . . . . ?
C8 C9 C10 O5 -53.8(4) . . . . ?
C8 C9 C10' O4' -32.3(5) . . . . ?
C8 C9 C10' O5' 147.6(2) . . . . ?
C9 C12 C13 C14 -79.72(15) . . . . ?
C9 C12 C13 C18 99.69(14) . . . . ?
C12 O2 C19 O3 176.59(15) . . . . ?
C12 O2 C19 C20 -1.26(13) . . . . ?
C12 N1 C20 C19 -1.83(16) . . . . ?
C12 N1 C20 C21 177.82(14) . . . . ?
C12 C9 C10 O4 -91.0(4) . . . . ?
C12 C9 C10 O5 85.8(3) . . . . ?
C12 C9 C10' O4' 86.2(4) . . . . ?
C12 C9 C10' O5' -93.9(3) . . . . ?
C12 C13 C14 C15 179.64(14) . . . . ?
C12 C13 C18 C17 179.66(14) . . . . ?
C13 C14 C15 C16 0.8(3) . . . . ?
C14 C13 C18 C17 -0.9(2) . . . . ?
C14 C15 C16 C17 -1.1(3) . . . . ?
C15 C16 C17 C18 0.4(3) . . . . ?
C16 C17 C18 C13 0.6(3) . . . . ?
C18 C13 C14 C15 0.2(2) . . . . ?
C19 O2 C12 N1 0.27(13) . . . . ?
C19 O2 C12 C9 118.76(12) . . . . ?
C19 O2 C12 C13 -118.32(11) . . . . ?
C19 C20 C21 C22 -159.90(15) . . . . ?
C19 C20 C21 C23 76.47(19) . . . . ?
C20 N1 C12 O2 1.03(15) . . . . ?
C20 N1 C12 C9 -116.85(13) . . . . ?
C20 N1 C12 C13 119.00(12) . . . . ?
C24 C3 C4 C5 179.19(18) . . . . ?
C10 C9 C12 O2 -86.7(3) . . . . ?
C10 C9 C12 N1 29.8(3) . . . . ?
C10 C9 C12 C13 152.5(3) . . . . ?
C10 C9 C10' O4' -168.8(7) . . . . ?
C10 C9 C10' O5' 11.0(3) . . . . ?
C11 O5 C10 C9 -176.3(4) . . . . ?
C11 O5 C10 O4 0.7(7) . . . . ?
C10' C9 C12 O2 -55.2(2) . . . . ?
C10' C9 C12 N1 61.3(3) . . . . ?
C10' C9 C12 C13 -176.0(2) . . . . ?
C10' C9 C10 O4 -177.3(6) . . . . ?
C10' C9 C10 O5 -0.5(4) . . . . ?
C11' O5' C10' C9 179.7(3) . . . . ?
C11' O5' C10' O4' -0.4(6) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
