# Electronic Supplementary Material (ESI) for CrystEngComm.
# 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. 
# 
#######################################################################

data_f
_database_code_depnum_ccdc_archive 'CCDC 2334117'
loop_
_audit_author_name
_audit_author_address
'tian fanyu'
;Shanghai Institute of Materia Medica
China
;
_audit_update_record             
;
2024-02-21 deposited with the CCDC.	2024-04-24 downloaded from the CCDC.
;
_audit_creation_date             2024-02-21
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H24 O6, C5 H9 N O2'
_chemical_formula_sum            'C26 H33 N O8'
_chemical_formula_weight         487.53
_chemical_absolute_configuration .
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           18
_space_group_name_H-M_alt        'P 21 21 2'
_space_group_name_Hall           'P 2 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'-x+1/2, y+1/2, -z'
'x+1/2, -y+1/2, -z'

_cell_length_a                   18.4944(8)
_cell_length_b                   23.2557(11)
_cell_length_c                   5.4935(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2362.76(17)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3797
_cell_measurement_temperature    170
_cell_measurement_theta_max      25.786
_cell_measurement_theta_min      2.370
_shelx_estimated_absorpt_T_max   0.997
_shelx_estimated_absorpt_T_min   0.991
_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6751
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1459 before and 0.0545 after correction. The Ratio of minimum to maximum transmission is 0.9057. 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    1.371
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1040
_exptl_crystal_size_max          0.09
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.03
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0692
_diffrn_reflns_av_unetI/netI     0.0614
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       5
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            21614
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.369
_diffrn_reflns_theta_min         2.069
_diffrn_ambient_temperature      170.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.716
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.988
_reflns_number_gt                3400
_reflns_number_total             4792
_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 V8.40A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.268
_refine_diff_density_min         -0.206
_refine_diff_density_rms         0.050
_refine_ls_abs_structure_details 
;
 Flack x determined using 1055 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.5(8)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     324
_refine_ls_number_reflns         4792
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0909
_refine_ls_R_factor_gt           0.0516
_refine_ls_restrained_S_all      1.082
_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)+(0.0445P)²+0.6093P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1026
_refine_ls_wR_factor_ref         0.1215
_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,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Restrained distances
 O1-H1
 0.87 with sigma of 0.02
3.a Ternary CH refined with riding coordinates:
 C22(H22)
3.b Secondary CH2 refined with riding coordinates:
 N1(H1c,H1d), C7(H7a,H7b), C6(H6a,H6b), C2(H2a,H2b), C1(H1a,H1b), C24(H24a,
 H24b), C25(H25a,H25b), C23(H23a,H23b)
3.c Aromatic/amide H refined with riding coordinates:
 C19(H19), C4(H4a), C20(H20), C16(H16), C9(H9), C13(H13), C12(H12)
3.d Idealised Me refined as rotating group:
 C14(H14a,H14b,H14c), C21(H21a,H21b,H21c)
3.e Idealised tetrahedral OH refined as rotating group:
 O6(H6), O4(H4)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_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
O5 O 0.71021(14) 0.06969(11) 0.4335(5) 0.0338(7) Uani 1 1 d . . . . .
O6 O 0.62369(16) 0.05694(12) 0.8317(5) 0.0370(7) Uani 1 1 d . . . . .
H6 H 0.652375 0.033130 0.769246 0.055 Uiso 1 1 calc GR . . . .
O3 O 0.70196(14) 0.75336(11) 0.3682(5) 0.0358(7) Uani 1 1 d . . . . .
O8 O 0.19464(15) 0.54372(12) 0.1933(5) 0.0360(7) Uani 1 1 d . . . . .
O4 O 0.61960(14) 0.76692(11) 0.7702(5) 0.0336(7) Uani 1 1 d . . . . .
H4 H 0.648482 0.789836 0.703043 0.050 Uiso 1 1 calc GR . . . .
O7 O 0.19867(15) 0.63630(11) 0.2939(5) 0.0368(7) Uani 1 1 d . . . . .
O1 O 0.6209(2) 0.46219(13) -0.0660(5) 0.0490(9) Uani 1 1 d D . . . .
O2 O 0.6195(2) 0.35444(12) -0.0487(5) 0.0554(10) Uani 1 1 d . . . . .
N1 N 0.16671(17) 0.62052(15) 0.7596(6) 0.0355(8) Uani 1 1 d . . . . .
H1C H 0.186972 0.613699 0.907769 0.043 Uiso 1 1 calc R . . . .
H1D H 0.191059 0.649886 0.687072 0.043 Uiso 1 1 calc R . . . .
C10 C 0.6527(2) 0.71061(16) 0.4178(7) 0.0288(9) Uani 1 1 d . . . . .
C26 C 0.18976(19) 0.58395(19) 0.3424(7) 0.0308(9) Uani 1 1 d . . . . .
C18 C 0.6166(2) 0.10300(15) 0.6815(7) 0.0276(9) Uani 1 1 d . . . . .
C15 C 0.5952(2) 0.19984(17) 0.3861(7) 0.0285(9) Uani 1 1 d . . . . .
C19 C 0.5650(2) 0.14381(16) 0.7406(8) 0.0307(9) Uani 1 1 d . . . . .
H19 H 0.536377 0.138980 0.882722 0.037 Uiso 1 1 calc R . . . .
C4 C 0.62611(19) 0.41118(16) 0.2981(7) 0.0278(8) Uani 1 1 d . . . . .
H4A H 0.627781 0.412518 0.470868 0.033 Uiso 1 1 calc R . . . .
C20 C 0.5548(2) 0.19166(17) 0.5943(8) 0.0322(10) Uani 1 1 d . . . . .
H20 H 0.519257 0.219318 0.638097 0.039 Uiso 1 1 calc R . . . .
C11 C 0.6117(2) 0.71904(16) 0.6280(7) 0.0274(9) Uani 1 1 d . . . . .
C8 C 0.5910(2) 0.62036(17) 0.3432(8) 0.0307(9) Uani 1 1 d . . . . .
C14 C 0.7552(2) 0.74164(18) 0.1847(7) 0.0333(9) Uani 1 1 d . . . . .
H14A H 0.731441 0.738160 0.025905 0.050 Uiso 1 1 calc GR . . . .
H14B H 0.780153 0.705600 0.223317 0.050 Uiso 1 1 calc GR . . . .
H14C H 0.790345 0.773148 0.179530 0.050 Uiso 1 1 calc GR . . . .
C17 C 0.6589(2) 0.11153(16) 0.4756(7) 0.0271(9) Uani 1 1 d . . . . .
C16 C 0.64802(19) 0.15918(16) 0.3286(7) 0.0282(9) Uani 1 1 d . . . . .
H16 H 0.676805 0.164217 0.186964 0.034 Uiso 1 1 calc R . . . .
C7 C 0.5854(2) 0.25325(16) 0.2341(7) 0.0322(9) Uani 1 1 d . . . . .
H7A H 0.533678 0.264343 0.235524 0.039 Uiso 1 1 calc R . . . .
H7B H 0.599048 0.244710 0.063703 0.039 Uiso 1 1 calc R . . . .
C5 C 0.6244(2) 0.35777(17) 0.1838(8) 0.0346(9) Uani 1 1 d . . . . .
C9 C 0.6424(2) 0.66168(16) 0.2776(8) 0.0317(9) Uani 1 1 d . . . . .
H9 H 0.670590 0.656153 0.135039 0.038 Uiso 1 1 calc R . . . .
C13 C 0.5508(2) 0.62960(17) 0.5525(8) 0.0340(10) Uani 1 1 d . . . . .
H13 H 0.515667 0.601956 0.599847 0.041 Uiso 1 1 calc R . . . .
C12 C 0.5608(2) 0.67880(17) 0.6958(8) 0.0318(9) Uani 1 1 d . . . . .
H12 H 0.532637 0.684404 0.838549 0.038 Uiso 1 1 calc R . . . .
C3 C 0.6255(2) 0.46203(17) 0.1708(7) 0.0330(9) Uani 1 1 d . . . . .
C6 C 0.6305(2) 0.30338(15) 0.3260(7) 0.0350(10) Uani 1 1 d . . . . .
H6A H 0.616331 0.311453 0.496428 0.042 Uiso 1 1 calc R . . . .
H6B H 0.681852 0.291448 0.327396 0.042 Uiso 1 1 calc R . . . .
C21 C 0.7587(2) 0.07882(18) 0.2366(7) 0.0349(10) Uani 1 1 d . . . . .
H21A H 0.731264 0.082650 0.084883 0.052 Uiso 1 1 calc GR . . . .
H21B H 0.791852 0.046068 0.223717 0.052 Uiso 1 1 calc GR . . . .
H21C H 0.786539 0.114044 0.265359 0.052 Uiso 1 1 calc GR . . . .
C2 C 0.6324(2) 0.51896(16) 0.2926(8) 0.0352(10) Uani 1 1 d . . . . .
H2A H 0.682962 0.532248 0.274905 0.042 Uiso 1 1 calc R . . . .
H2B H 0.623033 0.513698 0.468596 0.042 Uiso 1 1 calc R . . . .
C22 C 0.1701(2) 0.56753(17) 0.6046(8) 0.0338(10) Uani 1 1 d . . . . .
H22 H 0.206936 0.540302 0.671414 0.041 Uiso 1 1 calc R . . . .
C1 C 0.5828(2) 0.56587(16) 0.1991(9) 0.0362(10) Uani 1 1 d . . . . .
H1A H 0.593990 0.573678 0.026050 0.043 Uiso 1 1 calc R . . . .
H1B H 0.532017 0.552564 0.208971 0.043 Uiso 1 1 calc R . . . .
C24 C 0.0523(2) 0.57800(18) 0.7988(9) 0.0436(11) Uani 1 1 d . . . . .
H24A H 0.001071 0.580968 0.747557 0.052 Uiso 1 1 calc R . . . .
H24B H 0.054224 0.562048 0.965699 0.052 Uiso 1 1 calc R . . . .
C25 C 0.0888(2) 0.63550(18) 0.7873(9) 0.0398(11) Uani 1 1 d . . . . .
H25A H 0.071315 0.658123 0.646387 0.048 Uiso 1 1 calc R . . . .
H25B H 0.080350 0.657741 0.938326 0.048 Uiso 1 1 calc R . . . .
C23 C 0.0947(3) 0.5410(2) 0.6240(10) 0.0559(15) Uani 1 1 d . . . . .
H23A H 0.071010 0.540388 0.462453 0.067 Uiso 1 1 calc R . . . .
H23B H 0.097922 0.501096 0.685573 0.067 Uiso 1 1 calc R . . . .
H1 H 0.619(5) 0.4247(16) -0.112(16) 0.19(4) Uiso 1 1 d D . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O5 C17 1.378(4) . ?
O5 C21 1.421(4) . ?
O6 H6 0.8400 . ?
O6 C18 1.358(4) . ?
O3 C10 1.376(4) . ?
O3 C14 1.435(4) . ?
O8 C26 1.247(5) . ?
O4 H4 0.8400 . ?
O4 C11 1.368(4) . ?
O7 C26 1.257(5) . ?
O1 C3 1.303(5) . ?
O1 H1 0.91(3) . ?
O2 C5 1.283(5) . ?
N1 H1C 0.9100 . ?
N1 H1D 0.9100 . ?
N1 C22 1.499(5) . ?
N1 C25 1.491(5) . ?
C10 C11 1.395(5) . ?
C10 C9 1.387(5) . ?
C26 C22 1.534(5) . ?
C18 C19 1.384(5) . ?
C18 C17 1.391(5) . ?
C15 C20 1.380(6) . ?
C15 C16 1.395(5) . ?
C15 C7 1.508(5) . ?
C19 H19 0.9500 . ?
C19 C20 1.386(6) . ?
C4 H4A 0.9500 . ?
C4 C5 1.392(5) . ?
C4 C3 1.374(5) . ?
C20 H20 0.9500 . ?
C11 C12 1.379(5) . ?
C8 C9 1.399(5) . ?
C8 C13 1.386(6) . ?
C8 C1 1.502(5) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C17 C16 1.386(5) . ?
C16 H16 0.9500 . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C6 1.520(5) . ?
C5 C6 1.491(5) . ?
C9 H9 0.9500 . ?
C13 H13 0.9500 . ?
C13 C12 1.401(5) . ?
C12 H12 0.9500 . ?
C3 C2 1.489(5) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C1 1.515(5) . ?
C22 H22 1.0000 . ?
C22 C23 1.528(6) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C24 C25 1.499(6) . ?
C24 C23 1.509(6) . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?

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
C17 O5 C21 117.2(3) . . ?
C18 O6 H6 109.5 . . ?
C10 O3 C14 117.1(3) . . ?
C11 O4 H4 109.5 . . ?
C3 O1 H1 106(6) . . ?
H1C N1 H1D 108.6 . . ?
C22 N1 H1C 110.3 . . ?
C22 N1 H1D 110.3 . . ?
C25 N1 H1C 110.3 . . ?
C25 N1 H1D 110.3 . . ?
C25 N1 C22 106.9(3) . . ?
O3 C10 C11 115.0(3) . . ?
O3 C10 C9 125.0(4) . . ?
C9 C10 C11 120.0(4) . . ?
O8 C26 O7 125.3(4) . . ?
O8 C26 C22 116.6(4) . . ?
O7 C26 C22 118.1(4) . . ?
O6 C18 C19 117.7(4) . . ?
O6 C18 C17 123.5(3) . . ?
C19 C18 C17 118.8(3) . . ?
C20 C15 C16 118.3(4) . . ?
C20 C15 C7 120.4(4) . . ?
C16 C15 C7 121.2(4) . . ?
C18 C19 H19 119.7 . . ?
C18 C19 C20 120.6(4) . . ?
C20 C19 H19 119.7 . . ?
C5 C4 H4A 118.7 . . ?
C3 C4 H4A 118.7 . . ?
C3 C4 C5 122.5(4) . . ?
C15 C20 C19 121.1(4) . . ?
C15 C20 H20 119.4 . . ?
C19 C20 H20 119.4 . . ?
O4 C11 C10 121.9(3) . . ?
O4 C11 C12 118.1(3) . . ?
C12 C11 C10 120.0(4) . . ?
C9 C8 C1 120.8(4) . . ?
C13 C8 C9 118.2(4) . . ?
C13 C8 C1 120.9(4) . . ?
O3 C14 H14A 109.5 . . ?
O3 C14 H14B 109.5 . . ?
O3 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
O5 C17 C18 115.1(3) . . ?
O5 C17 C16 124.5(3) . . ?
C16 C17 C18 120.4(3) . . ?
C15 C16 H16 119.6 . . ?
C17 C16 C15 120.8(4) . . ?
C17 C16 H16 119.6 . . ?
C15 C7 H7A 109.1 . . ?
C15 C7 H7B 109.1 . . ?
C15 C7 C6 112.4(3) . . ?
H7A C7 H7B 107.9 . . ?
C6 C7 H7A 109.1 . . ?
C6 C7 H7B 109.1 . . ?
O2 C5 C4 120.3(4) . . ?
O2 C5 C6 118.4(4) . . ?
C4 C5 C6 121.2(4) . . ?
C10 C9 C8 120.9(4) . . ?
C10 C9 H9 119.5 . . ?
C8 C9 H9 119.5 . . ?
C8 C13 H13 119.3 . . ?
C8 C13 C12 121.5(4) . . ?
C12 C13 H13 119.3 . . ?
C11 C12 C13 119.5(4) . . ?
C11 C12 H12 120.3 . . ?
C13 C12 H12 120.3 . . ?
O1 C3 C4 120.7(4) . . ?
O1 C3 C2 116.8(4) . . ?
C4 C3 C2 122.4(4) . . ?
C7 C6 H6A 108.3 . . ?
C7 C6 H6B 108.3 . . ?
C5 C6 C7 115.8(3) . . ?
C5 C6 H6A 108.3 . . ?
C5 C6 H6B 108.3 . . ?
H6A C6 H6B 107.4 . . ?
O5 C21 H21A 109.5 . . ?
O5 C21 H21B 109.5 . . ?
O5 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C3 C2 H2A 108.3 . . ?
C3 C2 H2B 108.3 . . ?
C3 C2 C1 115.9(4) . . ?
H2A C2 H2B 107.4 . . ?
C1 C2 H2A 108.3 . . ?
C1 C2 H2B 108.3 . . ?
N1 C22 C26 109.8(3) . . ?
N1 C22 H22 109.9 . . ?
N1 C22 C23 104.7(3) . . ?
C26 C22 H22 109.9 . . ?
C23 C22 C26 112.5(4) . . ?
C23 C22 H22 109.9 . . ?
C8 C1 C2 111.6(3) . . ?
C8 C1 H1A 109.3 . . ?
C8 C1 H1B 109.3 . . ?
C2 C1 H1A 109.3 . . ?
C2 C1 H1B 109.3 . . ?
H1A C1 H1B 108.0 . . ?
H24A C24 H24B 108.9 . . ?
C25 C24 H24A 110.9 . . ?
C25 C24 H24B 110.9 . . ?
C25 C24 C23 104.3(3) . . ?
C23 C24 H24A 110.9 . . ?
C23 C24 H24B 110.9 . . ?
N1 C25 C24 103.4(3) . . ?
N1 C25 H25A 111.1 . . ?
N1 C25 H25B 111.1 . . ?
C24 C25 H25A 111.1 . . ?
C24 C25 H25B 111.1 . . ?
H25A C25 H25B 109.1 . . ?
C22 C23 H23A 110.4 . . ?
C22 C23 H23B 110.4 . . ?
C24 C23 C22 106.8(4) . . ?
C24 C23 H23A 110.4 . . ?
C24 C23 H23B 110.4 . . ?
H23A C23 H23B 108.6 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O6 H6 O8 0.84 1.96 2.687(4) 144.0 4_556 yes
O4 H4 O7 0.84 1.95 2.707(4) 148.9 4_566 yes

_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_mo_2022905_0m
_database_code_depnum_ccdc_archive 'CCDC 2334120'
loop_
_audit_author_name
_audit_author_address
'tian fanyu'
;Shanghai Institute of Materia Medica
China
;
_audit_update_record             
;
2024-02-21 deposited with the CCDC.	2024-04-24 downloaded from the CCDC.
;
_audit_creation_date             2024-02-21
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '0.5(C42 H48 O12), C10 H8 N2'
_chemical_formula_sum            'C31 H32 N2 O6'
_chemical_formula_weight         528.58
_chemical_absolute_configuration .
_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           5
_space_group_name_H-M_alt        'C 1 2 1'
_space_group_name_Hall           'C 2y'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'

_cell_length_a                   13.421(5)
_cell_length_b                   6.843(3)
_cell_length_c                   14.762(4)
_cell_angle_alpha                90
_cell_angle_beta                 101.980(12)
_cell_angle_gamma                90
_cell_volume                     1326.2(8)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1179
_cell_measurement_temperature    170
_cell_measurement_theta_max      23.31
_cell_measurement_theta_min      2.82
_shelx_estimated_absorpt_T_max   0.996
_shelx_estimated_absorpt_T_min   0.993
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6474
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0719 before and 0.0610 after correction.
The Ratio of minimum to maximum transmission is 0.8685.
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    1.324
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.04
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0545
_diffrn_reflns_av_unetI/netI     0.0823
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            5043
_diffrn_reflns_point_group_measured_fraction_full 0.897
_diffrn_reflns_point_group_measured_fraction_max 0.873
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.363
_diffrn_reflns_theta_min         2.821
_diffrn_ambient_temperature      170.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.619
_reflns_Friedel_fraction_full    0.777
_reflns_Friedel_fraction_max     0.732
_reflns_number_gt                1550
_reflns_number_total             2378
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.460
_refine_diff_density_min         -0.379
_refine_diff_density_rms         0.065
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   -1(4)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     276
_refine_ls_number_reflns         2378
_refine_ls_number_restraints     705
_refine_ls_R_factor_all          0.1214
_refine_ls_R_factor_gt           0.0719
_refine_ls_restrained_S_all      0.961
_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)+(0.0815P)²+2.1188P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1621
_refine_ls_wR_factor_ref         0.1985
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 2(4)
 -1(4)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
3. Rigid bond restraints
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
All non-hydrogen atoms have similar U: within 2A with sigma of 0.04 and sigma
for terminal atoms of 0.08
Uanis(C7) \\sim Ueq, Uanis(C6) \\sim Ueq, Uanis(C5) \\sim Ueq, Uanis(O2) \\sim
Ueq, Uanis(C21) \\sim Ueq, Uanis(O5) \\sim Ueq, Uanis(C18) \\sim Ueq, Uanis(O6)
\\sim Ueq, Uanis(C17) \\sim Ueq, Uanis(C16) \\sim Ueq, Uanis(C15) \\sim Ueq,
Uanis(C20) \\sim Ueq, Uanis(C19) \\sim Ueq, Uanis(C3) \\sim Ueq, Uanis(C2)
\\sim Ueq, Uanis(C1) \\sim Ueq, Uanis(C8) \\sim Ueq, Uanis(C9) \\sim Ueq,
Uanis(C10) \\sim Ueq, Uanis(O3) \\sim Ueq, Uanis(C14) \\sim Ueq, Uanis(C11)
\\sim Ueq, Uanis(O4) \\sim Ueq, Uanis(C12) \\sim Ueq, Uanis(C13) \\sim Ueq,
Uanis(C26) \\sim Ueq, Uanis(N1) \\sim Ueq, Uanis(C22) \\sim Ueq, Uanis(C23)
\\sim Ueq, Uanis(C24) \\sim Ueq, Uanis(C25) \\sim Ueq: with sigma of 0.005 and
sigma for terminal atoms of 0.01
Uanis(O2) \\sim Ueq, Uanis(O1) \\sim Ueq: with sigma of 0.001 and sigma for
terminal atoms of 0.002
5. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
6. Others
 Fixed Sof: O1(0.5) H1(0.5) O2(0.5) O4(0.5) H4(0.5) O6(0.5) H6(0.5) O3(0.5)
 O5(0.5) C11(0.5) C3(0.5) C5(0.5) C13(0.5) H13(0.5) C20(0.5) H20(0.5) C19(0.5)
 H19(0.5) C18(0.5) C17(0.5) C16(0.5) H16(0.5) C15(0.5) C12(0.5) H12(0.5)
 C10(0.5) C9(0.5) H9(0.5) C2(0.5) H2a(0.5) H2b(0.5) C6(0.5) H6a(0.5) H6b(0.5)
 C8(0.5) H4a(0.5) C1(0.5) H1a(0.5) H1b(0.5) C7(0.5) H7a(0.5) H7b(0.5) C14(0.5)
 H14a(0.5) H14b(0.5) H14c(0.5) C21(0.5) H21a(0.5) H21b(0.5) H21c(0.5)
7.a Secondary CH2 refined with riding coordinates:
 C2(H2a,H2b), C6(H6a,H6b), C1(H1a,H1b), C7(H7a,H7b)
7.b Aromatic/amide H refined with riding coordinates:
 C13(H13), C20(H20), C19(H19), C16(H16), C12(H12), C25(H25), C26(H26),
 C22(H22), C23(H23), C9(H9), C4(H4a)
7.c Fitted hexagon refined as free rotating group:
 C20(C19,C18,C17,C16,C15), C25(C26,N1,C22,C23,C24)
7.d Idealised Me refined as rotating group:
 C14(H14a,H14b,H14c), C21(H21a,H21b,H21c)
7.e Idealised tetrahedral OH refined as rotating group:
 O1(H1), O4(H4), O6(H6)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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 0.5876(12) 0.543(3) 0.5452(10) 0.035(4) Uani 0.5 1 d . U . A -1
H1 H 0.531353 0.499839 0.516220 0.053 Uiso 0.5 1 calc GR . . A -1
O2 O 0.4209(12) 0.554(3) 0.4352(9) 0.034(3) Uani 0.5 1 d . U . B -1
O4 O 1.032(3) 1.353(6) 0.8383(19) 0.035(5) Uani 0.5 1 d . U . A -1
H4 H 1.091700 1.324416 0.832620 0.052 Uiso 0.5 1 calc GR . . A -1
O6 O -0.041(3) 1.368(6) 0.1811(19) 0.039(6) Uani 0.5 1 d . U . B -1
H6 H -0.082163 1.283893 0.154168 0.059 Uiso 0.5 1 calc GR . . B -1
O3 O 1.0641(18) 1.000(4) 0.7646(11) 0.034(4) Uani 0.5 1 d . U . A -1
O5 O -0.0610(19) 0.996(4) 0.2124(12) 0.038(4) Uani 0.5 1 d . U . B -1
C11 C 0.9615(19) 1.273(4) 0.764(2) 0.034(5) Uani 0.5 1 d . U . A -1
C3 C 0.579(3) 0.747(4) 0.562(2) 0.034(4) Uani 0.5 1 d . U . A -1
C5 C 0.417(3) 0.720(4) 0.450(2) 0.028(4) Uani 0.5 1 d . U . B -1
C13 C 0.7962(16) 1.270(3) 0.6619(15) 0.031(4) Uani 0.5 1 d . U . A -1
H13 H 0.737378 1.341983 0.633303 0.038 Uiso 0.5 1 calc R . . A -1
C20 C 0.2085(14) 1.304(2) 0.3241(13) 0.033(5) Uani 0.5 1 d . U . B -1
H20 H 0.269860 1.375579 0.343421 0.039 Uiso 0.5 1 calc R . . B -1
C19 C 0.1281(18) 1.385(3) 0.2606(15) 0.036(5) Uani 0.5 1 d G U . B -1
H19 H 0.134488 1.512387 0.236566 0.043 Uiso 0.5 1 calc R . . B -1
C18 C 0.0383(17) 1.281(4) 0.232(2) 0.035(5) Uani 0.5 1 d G U . B -1
C17 C 0.0289(15) 1.095(4) 0.2674(19) 0.034(5) Uani 0.5 1 d G U . B -1
C16 C 0.1093(16) 1.013(2) 0.3308(14) 0.032(4) Uani 0.5 1 d G U . B -1
H16 H 0.102844 0.886175 0.354862 0.038 Uiso 0.5 1 calc R . . B -1
C15 C 0.1991(14) 1.118(2) 0.3592(14) 0.029(4) Uani 0.5 1 d G U . B -1
C12 C 0.8714(19) 1.362(3) 0.7250(16) 0.032(4) Uani 0.5 1 d . U . A -1
H12 H 0.860412 1.493221 0.742222 0.039 Uiso 0.5 1 calc R . . A -1
C10 C 0.9699(17) 1.072(4) 0.740(2) 0.033(4) Uani 0.5 1 d . U . A -1
C25 C 0.4037(3) 0.4374(6) 0.9287(3) 0.0431(17) Uani 1 1 d . U . . .
H25 H 0.444821 0.550540 0.929233 0.052 Uiso 1 1 calc R . . . .
C26 C 0.3023(3) 0.4403(7) 0.8823(3) 0.0498(18) Uani 1 1 d G U . . .
H26 H 0.274250 0.555440 0.851103 0.060 Uiso 1 1 calc R . . . .
N1 N 0.2421(2) 0.2748(8) 0.8815(3) 0.0432(14) Uani 1 1 d G U . . .
C22 C 0.2833(3) 0.1064(7) 0.9271(3) 0.0474(18) Uani 1 1 d G U . . .
H22 H 0.242099 -0.006723 0.926561 0.057 Uiso 1 1 calc R . . . .
C23 C 0.3846(3) 0.1035(7) 0.9735(3) 0.0444(17) Uani 1 1 d G U . . .
H23 H 0.412670 -0.011628 1.004692 0.053 Uiso 1 1 calc R . . . .
C24 C 0.4448(2) 0.2690(7) 0.9743(3) 0.0338(14) Uani 1 1 d G U . . .
C9 C 0.8948(18) 0.978(3) 0.6810(15) 0.034(4) Uani 0.5 1 d . U . A -1
H9 H 0.902791 0.843969 0.667143 0.041 Uiso 0.5 1 calc R . . A -1
C2 C 0.6740(18) 0.822(4) 0.6097(14) 0.038(5) Uani 0.5 1 d . U . A -1
H2A H 0.726763 0.722430 0.606896 0.046 Uiso 0.5 1 calc R . . A -1
H2B H 0.670456 0.837672 0.675596 0.046 Uiso 0.5 1 calc R . . A -1
C6 C 0.3396(17) 0.851(4) 0.3733(13) 0.034(4) Uani 0.5 1 d . U . B -1
H6A H 0.378484 0.932908 0.337422 0.041 Uiso 0.5 1 calc R . . B -1
H6B H 0.293086 0.765504 0.329839 0.041 Uiso 0.5 1 calc R . . B -1
C8 C 0.8043(17) 1.078(3) 0.6396(16) 0.034(4) Uani 0.5 1 d . U . A -1
C4 C 0.500000 0.8310(16) 0.500000 0.051(3) Uani 1 2 d S TU P . .
H4A H 0.500759 0.968264 0.490507 0.062 Uiso 0.5 1 calc R . . A .
C1 C 0.711(2) 1.024(3) 0.5746(19) 0.037(5) Uani 0.5 1 d . U . A -1
H1A H 0.724901 1.009778 0.511464 0.044 Uiso 0.5 1 calc R . . A -1
H1B H 0.658868 1.126549 0.573062 0.044 Uiso 0.5 1 calc R . . A -1
C7 C 0.279(2) 0.980(3) 0.4271(19) 0.039(5) Uani 0.5 1 d . U . B -1
H7A H 0.327056 1.062773 0.471059 0.047 Uiso 0.5 1 calc R . . B -1
H7B H 0.242022 0.896063 0.463517 0.047 Uiso 0.5 1 calc R . . B -1
C14 C 1.070(2) 0.797(4) 0.7483(16) 0.035(4) Uani 0.5 1 d . U . A -1
H14A H 1.066858 0.773773 0.682210 0.053 Uiso 0.5 1 calc GR . . A -1
H14B H 1.013032 0.729941 0.767177 0.053 Uiso 0.5 1 calc GR . . A -1
H14C H 1.134480 0.745504 0.784216 0.053 Uiso 0.5 1 calc GR . . A -1
C21 C -0.072(3) 0.786(5) 0.2235(17) 0.054(7) Uani 0.5 1 d . U . B -1
H21A H -0.022370 0.717514 0.194697 0.081 Uiso 0.5 1 calc GR . . B -1
H21B H -0.140949 0.746290 0.193613 0.081 Uiso 0.5 1 calc GR . . B -1
H21C H -0.059478 0.754277 0.289545 0.081 Uiso 0.5 1 calc GR . . B -1


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 H1 0.8400 . ?
O1 C3 1.43(3) . ?
O2 C5 1.16(3) . ?
O4 H4 0.8400 . ?
O4 C11 1.41(4) . ?
O6 H6 0.8400 . ?
O6 C18 1.31(4) . ?
O3 C10 1.33(3) . ?
O3 C14 1.42(4) . ?
O5 C17 1.47(3) . ?
O5 C21 1.45(4) . ?
C11 C12 1.371(17) . ?
C11 C10 1.43(2) . ?
C3 C2 1.42(4) . ?
C3 C4 1.37(3) . ?
C5 C6 1.63(4) . ?
C5 C4 1.42(3) . ?
C13 H13 0.9500 . ?
C13 C12 1.375(19) . ?
C13 C8 1.37(2) . ?
C20 H20 0.9500 . ?
C20 C19 1.3900 . ?
C20 C15 1.3900 . ?
C19 H19 0.9500 . ?
C19 C18 1.3900 . ?
C18 C17 1.3900 . ?
C17 C16 1.3900 . ?
C16 H16 0.9500 . ?
C16 C15 1.3900 . ?
C15 C7 1.61(3) . ?
C12 H12 0.9500 . ?
C10 C9 1.356(18) . ?
C25 H25 0.9500 . ?
C25 C26 1.3900 . ?
C25 C24 1.3900 . ?
C26 H26 0.9500 . ?
C26 N1 1.3900 . ?
N1 C22 1.3900 . ?
C22 H22 0.9500 . ?
C22 C23 1.3900 . ?
C23 H23 0.9500 . ?
C23 C24 1.3900 . ?
C24 C24 1.518(5) 2_657 ?
C9 H9 0.9500 . ?
C9 C8 1.416(19) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C1 1.60(3) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C6 C7 1.53(4) . ?
C8 C1 1.45(3) . ?
C4 H4A 0.9500 2_656 ?
C4 H4A 0.9500 . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 O1 H1 109.5 . . ?
C11 O4 H4 109.5 . . ?
C18 O6 H6 109.5 . . ?
C10 O3 C14 114(2) . . ?
C21 O5 C17 119(2) . . ?
O4 C11 C10 119(2) . . ?
C12 C11 O4 123(2) . . ?
C12 C11 C10 115.8(12) . . ?
C2 C3 O1 110(3) . . ?
C4 C3 O1 112(2) . . ?
C4 C3 C2 132(3) . . ?
O2 C5 C6 117(2) . . ?
O2 C5 C4 124(3) . . ?
C4 C5 C6 112.7(19) . . ?
C12 C13 H13 119.3 . . ?
C8 C13 H13 119.3 . . ?
C8 C13 C12 121.3(13) . . ?
C19 C20 H20 120.0 . . ?
C19 C20 C15 120.0 . . ?
C15 C20 H20 120.0 . . ?
C20 C19 H19 120.0 . . ?
C20 C19 C18 120.0 . . ?
C18 C19 H19 120.0 . . ?
O6 C18 C19 119(2) . . ?
O6 C18 C17 120(2) . . ?
C19 C18 C17 120.0 . . ?
C18 C17 O5 110.0(16) . . ?
C16 C17 O5 128.4(17) . . ?
C16 C17 C18 120.0 . . ?
C17 C16 H16 120.0 . . ?
C17 C16 C15 120.0 . . ?
C15 C16 H16 120.0 . . ?
C20 C15 C7 131.8(15) . . ?
C16 C15 C20 120.0 . . ?
C16 C15 C7 108.1(15) . . ?
C11 C12 C13 122.6(15) . . ?
C11 C12 H12 118.7 . . ?
C13 C12 H12 118.7 . . ?
O3 C10 C11 114(2) . . ?
O3 C10 C9 122(2) . . ?
C9 C10 C11 122.1(12) . . ?
C26 C25 H25 120.0 . . ?
C26 C25 C24 120.0 . . ?
C24 C25 H25 120.0 . . ?
C25 C26 H26 120.0 . . ?
N1 C26 C25 120.0 . . ?
N1 C26 H26 120.0 . . ?
C22 N1 C26 120.0 . . ?
N1 C22 H22 120.0 . . ?
N1 C22 C23 120.0 . . ?
C23 C22 H22 120.0 . . ?
C22 C23 H23 120.0 . . ?
C24 C23 C22 120.0 . . ?
C24 C23 H23 120.0 . . ?
C25 C24 C24 119.35(18) . 2_657 ?
C23 C24 C25 120.0 . . ?
C23 C24 C24 120.64(18) . 2_657 ?
C10 C9 H9 119.8 . . ?
C10 C9 C8 120.3(15) . . ?
C8 C9 H9 119.8 . . ?
C3 C2 H2A 107.9 . . ?
C3 C2 H2B 107.9 . . ?
C3 C2 C1 118(2) . . ?
H2A C2 H2B 107.2 . . ?
C1 C2 H2A 107.9 . . ?
C1 C2 H2B 107.9 . . ?
C5 C6 H6A 110.4 . . ?
C5 C6 H6B 110.4 . . ?
H6A C6 H6B 108.6 . . ?
C7 C6 C5 106.8(19) . . ?
C7 C6 H6A 110.4 . . ?
C7 C6 H6B 110.4 . . ?
C13 C8 C9 117.7(12) . . ?
C13 C8 C1 107.5(18) . . ?
C9 C8 C1 135(2) . . ?
C3 C4 C5 122.5(10) . . ?
C3 C4 H4A 110.2(12) . 2_656 ?
C3 C4 H4A 118.8 . . ?
C5 C4 H4A 118.8 . . ?
C5 C4 H4A 125.0(13) . 2_656 ?
H4A C4 H4A 17.3 . 2_656 ?
C2 C1 H1A 110.4 . . ?
C2 C1 H1B 110.4 . . ?
C8 C1 C2 107(2) . . ?
C8 C1 H1A 110.4 . . ?
C8 C1 H1B 110.4 . . ?
H1A C1 H1B 108.6 . . ?
C15 C7 H7A 109.3 . . ?
C15 C7 H7B 109.3 . . ?
C6 C7 C15 112(2) . . ?
C6 C7 H7A 109.3 . . ?
C6 C7 H7B 109.3 . . ?
H7A C7 H7B 107.9 . . ?
O3 C14 H14A 109.5 . . ?
O3 C14 H14B 109.5 . . ?
O3 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
O5 C21 H21A 109.5 . . ?
O5 C21 H21B 109.5 . . ?
O5 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?

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

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

data_mo_2023137_0m
_database_code_depnum_ccdc_archive 'CCDC 2334118'
loop_
_audit_author_name
_audit_author_address
'tian fanyu'
;Shanghai Institute of Materia Medica
China
;
_audit_update_record             
;
2024-02-21 deposited with the CCDC.	2024-04-24 downloaded from the CCDC.
;
_audit_creation_date             2024-02-21
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H24 O6, C5 H9 N O2'
_chemical_formula_sum            'C26 H33 N O8'
_chemical_formula_weight         487.53
_chemical_absolute_configuration .
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           18
_space_group_name_H-M_alt        'P 21 21 2'
_space_group_name_Hall           'P 2 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'x+1/2, -y+1/2, -z'
'-x+1/2, y+1/2, -z'

_cell_length_a                   18.370(4)
_cell_length_b                   23.190(8)
_cell_length_c                   5.4660(16)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2328.5(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2899
_cell_measurement_temperature    100
_cell_measurement_theta_max      24.412
_cell_measurement_theta_min      2.218
_shelx_estimated_absorpt_T_max   0.995
_shelx_estimated_absorpt_T_min   0.985
_exptl_absorpt_coefficient_mu    0.103
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6445
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1196 before and 0.0637 after correction. The Ratio of minimum to maximum transmission is 0.8646. 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    1.391
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1040
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0881
_diffrn_reflns_av_unetI/netI     0.0855
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       5
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            17672
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.411
_diffrn_reflns_theta_min         2.077
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.715
_reflns_Friedel_fraction_full    0.996
_reflns_Friedel_fraction_max     0.983
_reflns_number_gt                3277
_reflns_number_total             4722
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.493
_refine_diff_density_min         -0.304
_refine_diff_density_rms         0.068
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   1(2)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     322
_refine_ls_number_reflns         4722
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1097
_refine_ls_R_factor_gt           0.0657
_refine_ls_restrained_S_all      1.060
_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)+(0.0608P)²+1.5797P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1361
_refine_ls_wR_factor_ref         0.1592
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0(2)
 1(2)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
3.a Ternary CH refined with riding coordinates:
 C22(H22)
3.b Secondary CH2 refined with riding coordinates:
 C1(H1a,H1b), C2(H2a,H2b), C6(H6a,H6b), C7(H7a,H7b), N1(H1c,H1d), C24(H24a,
 H24b), C25(H25a,H25b), C23(H23a,H23b)
3.c Aromatic/amide H refined with riding coordinates:
 C16(H16), C12(H12), C4(H4a), C13(H13), C19(H19), C20(H20), C9(H9)
3.d Idealised Me refined as rotating group:
 C14(H14a,H14b,H14c), C21(H21a,H21b,H21c)
3.e Idealised tetrahedral OH refined as rotating group:
 O4(H4), O6(H6), O2(H2)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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
O3 O 0.28966(19) 0.43105(14) 0.0691(7) 0.0261(9) Uani 1 1 d . . . . .
O5 O 0.29688(19) -0.25313(15) 0.1227(7) 0.0273(9) Uani 1 1 d . . . . .
O4 O 0.3776(2) 0.44313(15) -0.3289(7) 0.0274(9) Uani 1 1 d . . . . .
H4 H 0.350554 0.467829 -0.262720 0.041 Uiso 1 1 calc GR . . . .
O6 O 0.38119(18) -0.26693(15) -0.2799(7) 0.0263(9) Uani 1 1 d . . . . .
H6 H 0.345950 -0.286679 -0.229199 0.039 Uiso 1 1 calc GR . . . .
O2 O 0.3800(3) 0.03716(16) 0.5686(7) 0.0390(11) Uani 1 1 d . . . . .
H2 H 0.382077 0.071243 0.620180 0.058 Uiso 1 1 calc GR . . . .
O1 O 0.3793(3) 0.14492(17) 0.5526(8) 0.0487(12) Uani 1 1 d . . . . .
C16 C 0.3573(3) -0.1620(2) 0.2196(11) 0.0249(12) Uani 1 1 d . . . . .
H16 H 0.328927 -0.156833 0.363259 0.030 Uiso 1 1 calc R . . . .
C12 C 0.4359(3) 0.3558(2) -0.2402(10) 0.0211(11) Uani 1 1 d . . . . .
H12 H 0.464491 0.360143 -0.383852 0.025 Uiso 1 1 calc R . . . .
C17 C 0.3469(3) -0.2107(2) 0.0750(11) 0.0253(12) Uani 1 1 d . . . . .
C14 C 0.2409(3) 0.4219(2) 0.2655(10) 0.0257(12) Uani 1 1 d . . . . .
H14A H 0.212293 0.387009 0.234915 0.039 Uiso 1 1 calc GR . . . .
H14B H 0.208125 0.455113 0.280059 0.039 Uiso 1 1 calc GR . . . .
H14C H 0.268477 0.417395 0.417800 0.039 Uiso 1 1 calc GR . . . .
C4 C 0.3732(3) 0.0890(2) 0.2035(10) 0.0232(11) Uani 1 1 d . . . . .
H4A H 0.371425 0.088011 0.029883 0.028 Uiso 1 1 calc R . . . .
C15 C 0.4095(3) -0.1206(2) 0.1540(11) 0.0257(12) Uani 1 1 d . . . . .
C11 C 0.3841(3) 0.3972(2) -0.1806(10) 0.0232(12) Uani 1 1 d . . . . .
C13 C 0.4459(3) 0.3079(2) -0.0900(10) 0.0229(12) Uani 1 1 d . . . . .
H13 H 0.481887 0.280169 -0.131398 0.027 Uiso 1 1 calc R . . . .
C19 C 0.4407(3) -0.1788(2) -0.2041(11) 0.0233(12) Uani 1 1 d . . . . .
H19 H 0.469183 -0.184161 -0.347320 0.028 Uiso 1 1 calc R . . . .
C8 C 0.4044(3) 0.3002(2) 0.1179(10) 0.0225(12) Uani 1 1 d . . . . .
C10 C 0.3409(3) 0.3889(2) 0.0274(10) 0.0209(12) Uani 1 1 d . . . . .
C3 C 0.3745(3) 0.1424(2) 0.3204(11) 0.0302(13) Uani 1 1 d . . . . .
C21 C 0.2437(3) -0.2413(2) 0.3080(10) 0.0254(12) Uani 1 1 d . . . . .
H21A H 0.219231 -0.204790 0.271404 0.038 Uiso 1 1 calc GR . . . .
H21B H 0.267749 -0.238665 0.467562 0.038 Uiso 1 1 calc GR . . . .
H21C H 0.207695 -0.272534 0.311555 0.038 Uiso 1 1 calc GR . . . .
C1 C 0.4143(3) 0.2464(2) 0.2723(10) 0.0229(12) Uani 1 1 d . . . . .
H1A H 0.466173 0.234865 0.269948 0.028 Uiso 1 1 calc R . . . .
H1B H 0.400792 0.255050 0.443740 0.028 Uiso 1 1 calc R . . . .
C18 C 0.3887(3) -0.2189(2) -0.1369(10) 0.0245(12) Uani 1 1 d . . . . .
C2 C 0.3683(3) 0.1971(2) 0.1798(11) 0.0308(13) Uani 1 1 d . . . . .
H2A H 0.316657 0.209387 0.180979 0.037 Uiso 1 1 calc R . . . .
H2B H 0.381831 0.189273 0.007672 0.037 Uiso 1 1 calc R . . . .
C20 C 0.4506(3) -0.1298(2) -0.0559(11) 0.0282(13) Uani 1 1 d . . . . .
H20 H 0.486365 -0.102129 -0.100614 0.034 Uiso 1 1 calc R . . . .
C6 C 0.3676(3) -0.0191(2) 0.2080(11) 0.0292(13) Uani 1 1 d . . . . .
H6A H 0.376610 -0.013577 0.031020 0.035 Uiso 1 1 calc R . . . .
H6B H 0.316688 -0.032551 0.226399 0.035 Uiso 1 1 calc R . . . .
C5 C 0.3744(3) 0.0375(2) 0.3308(11) 0.0289(13) Uani 1 1 d . . . . .
C9 C 0.3512(3) 0.3407(2) 0.1781(11) 0.0234(12) Uani 1 1 d . . . . .
H9 H 0.322181 0.335712 0.320351 0.028 Uiso 1 1 calc R . . . .
C7 C 0.4179(3) -0.0665(2) 0.2994(12) 0.0299(13) Uani 1 1 d . . . . .
H7A H 0.468932 -0.053114 0.288881 0.036 Uiso 1 1 calc R . . . .
H7B H 0.406920 -0.074646 0.473396 0.036 Uiso 1 1 calc R . . . .
O7 O 0.19602(19) 0.04220(15) 1.3077(7) 0.0247(8) Uani 1 1 d . . . . .
O8 O 0.19764(19) 0.13567(15) 1.2202(7) 0.0265(9) Uani 1 1 d . . . . .
N1 N 0.1672(2) 0.12303(19) 0.7476(8) 0.0241(10) Uani 1 1 d . . . . .
H1C H 0.187087 0.117798 0.596670 0.029 Uiso 1 1 calc R . . . .
H1D H 0.191644 0.152016 0.824199 0.029 Uiso 1 1 calc R . . . .
C22 C 0.1722(3) 0.0687(2) 0.8935(10) 0.0239(12) Uani 1 1 d . . . . .
H22 H 0.210486 0.042853 0.823653 0.029 Uiso 1 1 calc R . . . .
C24 C 0.0531(3) 0.0789(2) 0.6956(10) 0.0255(12) Uani 1 1 d . . . . .
H24A H 0.056951 0.065265 0.524438 0.031 Uiso 1 1 calc R . . . .
H24B H 0.001096 0.079962 0.743239 0.031 Uiso 1 1 calc R . . . .
C25 C 0.0882(3) 0.1376(2) 0.7259(11) 0.0265(13) Uani 1 1 d . . . . .
H25A H 0.078925 0.162481 0.581960 0.032 Uiso 1 1 calc R . . . .
H25B H 0.070289 0.157324 0.874904 0.032 Uiso 1 1 calc R . . . .
C23 C 0.0965(3) 0.0406(2) 0.8670(12) 0.0338(15) Uani 1 1 d . . . . .
H23A H 0.101005 0.001291 0.798276 0.041 Uiso 1 1 calc R . . . .
H23B H 0.072174 0.038012 1.028277 0.041 Uiso 1 1 calc R . . . .
C26 C 0.1902(2) 0.0833(2) 1.1631(10) 0.0234(12) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O3 C14 1.414(6) . ?
O3 C10 1.376(6) . ?
O5 C17 1.373(6) . ?
O5 C21 1.434(6) . ?
O4 H4 0.8400 . ?
O4 C11 1.343(6) . ?
O6 H6 0.8400 . ?
O6 C18 1.368(6) . ?
O2 H2 0.8400 . ?
O2 C5 1.304(7) . ?
O1 C3 1.274(7) . ?
C16 H16 0.9500 . ?
C16 C17 1.390(7) . ?
C16 C15 1.404(7) . ?
C12 H12 0.9500 . ?
C12 C11 1.390(7) . ?
C12 C13 1.393(7) . ?
C17 C18 1.402(8) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C4 H4A 0.9500 . ?
C4 C3 1.393(7) . ?
C4 C5 1.384(8) . ?
C15 C20 1.390(8) . ?
C15 C7 1.493(7) . ?
C11 C10 1.401(7) . ?
C13 H13 0.9500 . ?
C13 C8 1.380(8) . ?
C19 H19 0.9500 . ?
C19 C18 1.383(7) . ?
C19 C20 1.407(7) . ?
C8 C1 1.517(7) . ?
C8 C9 1.396(7) . ?
C10 C9 1.400(7) . ?
C3 C2 1.487(8) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C1 C2 1.510(7) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C20 H20 0.9500 . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C6 C5 1.480(7) . ?
C6 C7 1.520(7) . ?
C9 H9 0.9500 . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
O7 C26 1.243(6) . ?
O8 C26 1.260(6) . ?
N1 H1C 0.9100 . ?
N1 H1D 0.9100 . ?
N1 C22 1.493(6) . ?
N1 C25 1.495(6) . ?
C22 H22 1.0000 . ?
C22 C23 1.543(7) . ?
C22 C26 1.548(7) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C24 C25 1.517(7) . ?
C24 C23 1.517(7) . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?

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 O3 C14 116.9(4) . . ?
C17 O5 C21 117.0(4) . . ?
C11 O4 H4 109.5 . . ?
C18 O6 H6 109.5 . . ?
C5 O2 H2 109.5 . . ?
C17 C16 H16 119.9 . . ?
C17 C16 C15 120.2(5) . . ?
C15 C16 H16 119.9 . . ?
C11 C12 H12 119.9 . . ?
C11 C12 C13 120.2(5) . . ?
C13 C12 H12 119.9 . . ?
O5 C17 C16 124.4(5) . . ?
O5 C17 C18 115.2(5) . . ?
C16 C17 C18 120.4(5) . . ?
O3 C14 H14A 109.5 . . ?
O3 C14 H14B 109.5 . . ?
O3 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C3 C4 H4A 118.8 . . ?
C5 C4 H4A 118.8 . . ?
C5 C4 C3 122.5(5) . . ?
C16 C15 C7 120.6(5) . . ?
C20 C15 C16 118.5(5) . . ?
C20 C15 C7 120.8(5) . . ?
O4 C11 C12 117.9(5) . . ?
O4 C11 C10 123.2(5) . . ?
C12 C11 C10 118.9(5) . . ?
C12 C13 H13 119.5 . . ?
C8 C13 C12 121.1(5) . . ?
C8 C13 H13 119.5 . . ?
C18 C19 H19 120.7 . . ?
C18 C19 C20 118.6(5) . . ?
C20 C19 H19 120.7 . . ?
C13 C8 C1 119.9(5) . . ?
C13 C8 C9 119.6(5) . . ?
C9 C8 C1 120.4(5) . . ?
O3 C10 C11 115.1(4) . . ?
O3 C10 C9 124.2(5) . . ?
C9 C10 C11 120.7(4) . . ?
O1 C3 C4 119.9(5) . . ?
O1 C3 C2 118.7(5) . . ?
C4 C3 C2 121.3(5) . . ?
O5 C21 H21A 109.5 . . ?
O5 C21 H21B 109.5 . . ?
O5 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C8 C1 H1A 109.3 . . ?
C8 C1 H1B 109.3 . . ?
H1A C1 H1B 107.9 . . ?
C2 C1 C8 111.7(4) . . ?
C2 C1 H1A 109.3 . . ?
C2 C1 H1B 109.3 . . ?
O6 C18 C17 121.8(5) . . ?
O6 C18 C19 117.8(5) . . ?
C19 C18 C17 120.4(5) . . ?
C3 C2 C1 115.5(5) . . ?
C3 C2 H2A 108.4 . . ?
C3 C2 H2B 108.4 . . ?
C1 C2 H2A 108.4 . . ?
C1 C2 H2B 108.4 . . ?
H2A C2 H2B 107.5 . . ?
C15 C20 C19 121.9(5) . . ?
C15 C20 H20 119.0 . . ?
C19 C20 H20 119.0 . . ?
H6A C6 H6B 107.4 . . ?
C5 C6 H6A 108.3 . . ?
C5 C6 H6B 108.3 . . ?
C5 C6 C7 116.1(5) . . ?
C7 C6 H6A 108.3 . . ?
C7 C6 H6B 108.3 . . ?
O2 C5 C4 120.5(5) . . ?
O2 C5 C6 117.0(5) . . ?
C4 C5 C6 122.5(5) . . ?
C8 C9 C10 119.6(5) . . ?
C8 C9 H9 120.2 . . ?
C10 C9 H9 120.2 . . ?
C15 C7 C6 111.7(5) . . ?
C15 C7 H7A 109.3 . . ?
C15 C7 H7B 109.3 . . ?
C6 C7 H7A 109.3 . . ?
C6 C7 H7B 109.3 . . ?
H7A C7 H7B 107.9 . . ?
H1C N1 H1D 108.6 . . ?
C22 N1 H1C 110.3 . . ?
C22 N1 H1D 110.3 . . ?
C22 N1 C25 107.0(4) . . ?
C25 N1 H1C 110.3 . . ?
C25 N1 H1D 110.3 . . ?
N1 C22 H22 110.2 . . ?
N1 C22 C23 104.5(4) . . ?
N1 C22 C26 109.7(4) . . ?
C23 C22 H22 110.2 . . ?
C23 C22 C26 112.0(5) . . ?
C26 C22 H22 110.2 . . ?
H24A C24 H24B 109.0 . . ?
C25 C24 H24A 111.1 . . ?
C25 C24 H24B 111.1 . . ?
C25 C24 C23 103.5(4) . . ?
C23 C24 H24A 111.1 . . ?
C23 C24 H24B 111.1 . . ?
N1 C25 C24 102.6(4) . . ?
N1 C25 H25A 111.2 . . ?
N1 C25 H25B 111.2 . . ?
C24 C25 H25A 111.2 . . ?
C24 C25 H25B 111.2 . . ?
H25A C25 H25B 109.2 . . ?
C22 C23 H23A 110.4 . . ?
C22 C23 H23B 110.4 . . ?
C24 C23 C22 106.6(4) . . ?
C24 C23 H23A 110.4 . . ?
C24 C23 H23B 110.4 . . ?
H23A C23 H23B 108.6 . . ?
O7 C26 O8 124.9(5) . . ?
O7 C26 C22 117.1(5) . . ?
O8 C26 C22 118.0(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
O3 C10 C9 C8 179.5(5) . . . . ?
O5 C17 C18 O6 -2.0(7) . . . . ?
O5 C17 C18 C19 179.7(5) . . . . ?
O4 C11 C10 O3 0.8(7) . . . . ?
O4 C11 C10 C9 -178.7(5) . . . . ?
O1 C3 C2 C1 39.1(9) . . . . ?
C16 C17 C18 O6 178.3(5) . . . . ?
C16 C17 C18 C19 0.1(8) . . . . ?
C16 C15 C20 C19 0.7(8) . . . . ?
C16 C15 C7 C6 -88.2(6) . . . . ?
C12 C11 C10 O3 -178.2(4) . . . . ?
C12 C11 C10 C9 2.3(7) . . . . ?
C12 C13 C8 C1 177.4(5) . . . . ?
C12 C13 C8 C9 0.4(8) . . . . ?
C17 C16 C15 C20 -0.6(8) . . . . ?
C17 C16 C15 C7 176.2(5) . . . . ?
C14 O3 C10 C11 175.0(4) . . . . ?
C14 O3 C10 C9 -5.5(7) . . . . ?
C4 C3 C2 C1 -142.6(5) . . . . ?
C15 C16 C17 O5 -179.3(5) . . . . ?
C15 C16 C17 C18 0.3(8) . . . . ?
C11 C12 C13 C8 0.9(8) . . . . ?
C11 C10 C9 C8 -1.0(7) . . . . ?
C13 C12 C11 O4 178.7(5) . . . . ?
C13 C12 C11 C10 -2.2(7) . . . . ?
C13 C8 C1 C2 -86.2(6) . . . . ?
C13 C8 C9 C10 -0.3(7) . . . . ?
C8 C1 C2 C3 180.0(5) . . . . ?
C3 C4 C5 O2 -2.9(8) . . . . ?
C3 C4 C5 C6 175.3(5) . . . . ?
C21 O5 C17 C16 11.5(7) . . . . ?
C21 O5 C17 C18 -168.1(4) . . . . ?
C1 C8 C9 C10 -177.3(5) . . . . ?
C18 C19 C20 C15 -0.3(8) . . . . ?
C20 C15 C7 C6 88.6(6) . . . . ?
C20 C19 C18 O6 -178.4(4) . . . . ?
C20 C19 C18 C17 -0.1(7) . . . . ?
C5 C4 C3 O1 2.3(9) . . . . ?
C5 C4 C3 C2 -176.0(6) . . . . ?
C5 C6 C7 C15 -176.7(5) . . . . ?
C9 C8 C1 C2 90.7(6) . . . . ?
C7 C15 C20 C19 -176.2(5) . . . . ?
C7 C6 C5 O2 -43.7(8) . . . . ?
C7 C6 C5 C4 138.1(6) . . . . ?
N1 C22 C23 C24 2.9(6) . . . . ?
N1 C22 C26 O7 180.0(4) . . . . ?
N1 C22 C26 O8 0.1(6) . . . . ?
C22 N1 C25 C24 -37.8(5) . . . . ?
C25 N1 C22 C23 21.6(6) . . . . ?
C25 N1 C22 C26 -98.6(5) . . . . ?
C25 C24 C23 C22 -25.7(6) . . . . ?
C23 C22 C26 O7 64.4(6) . . . . ?
C23 C22 C26 O8 -115.5(5) . . . . ?
C23 C24 C25 N1 38.5(6) . . . . ?
C26 C22 C23 C24 121.6(5) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0(2)
2 1(2)

####################################################################### 
# 
# 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_mo_20231102_0m_4
_database_code_depnum_ccdc_archive 'CCDC 2334119'
loop_
_audit_author_name
_audit_author_address
'tian fanyu'
;Shanghai Institute of Materia Medica
China
;
_audit_update_record             
;
2024-02-21 deposited with the CCDC.	2024-04-24 downloaded from the CCDC.
;
_audit_creation_date             2024-02-21
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H24 O6, C5 H9 N O2'
_chemical_formula_sum            'C26 H33 N O8'
_chemical_formula_weight         487.53
_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           13
_space_group_name_H-M_alt        'P 1 2/n 1'
_space_group_name_Hall           '-P 2yac'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z-1/2'

_cell_length_a                   20.106(4)
_cell_length_b                   5.4996(10)
_cell_length_c                   23.399(5)
_cell_angle_alpha                90
_cell_angle_beta                 114.231(5)
_cell_angle_gamma                90
_cell_volume                     2359.4(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1220
_cell_measurement_temperature    170
_cell_measurement_theta_max      23.116
_cell_measurement_theta_min      2.259
_shelx_estimated_absorpt_T_max   0.996
_shelx_estimated_absorpt_T_min   0.988
_exptl_absorpt_coefficient_mu    0.102
_exptl_absorpt_correction_T_max  0.7523
_exptl_absorpt_correction_T_min  0.5236
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
 TWINABS-2012/1 (Bruker,2012) was used for absorption correction.

Final HKLF 4 output contains 20923 reflections, Rint = 0.0911
 (6016 with I > 3sig(I), Rint = 0.0543)
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.373
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1040
_exptl_crystal_size_max          0.12
_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  ?
_diffrn_reflns_av_unetI/netI     0.0899
_diffrn_reflns_Laue_measured_fraction_full 0.962
_diffrn_reflns_Laue_measured_fraction_max 0.953
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            4448
_diffrn_reflns_point_group_measured_fraction_full 0.962
_diffrn_reflns_point_group_measured_fraction_max 0.953
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.672
_diffrn_reflns_theta_min         1.909
_diffrn_ambient_temperature      170.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.962
_diffrn_measured_fraction_theta_max 0.953
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2853
_reflns_number_total             4448
_reflns_special_details          
;
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.413
_refine_diff_density_min         -0.323
_refine_diff_density_rms         0.079
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.090
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     367
_refine_ls_number_reflns         4448
_refine_ls_number_restraints     759
_refine_ls_R_factor_all          0.1541
_refine_ls_R_factor_gt           0.0993
_refine_ls_restrained_S_all      1.019
_refine_ls_shift/su_max          0.019
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0173P)²+9.7206P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1837
_refine_ls_wR_factor_ref         0.2087
_refine_special_details          
;
 Refined as a 2-component twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.6350(16)
 0.3650(16)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
3. Restrained distances
 C22-C26 \\sim C27-C26
 with sigma of 0.02
4. Rigid bond restraints
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
5. Uiso/Uaniso restraints and constraints
All non-hydrogen atoms have similar U: within 2A with sigma of 0.04 and sigma
for terminal atoms of 0.08
Uanis(C23) \\sim Ueq, Uanis(C22) \\sim Ueq: with sigma of 0.001 and sigma for
terminal atoms of 0.002
Uanis(C27) \\sim Ueq, Uanis(N2) \\sim Ueq: with sigma of 0.001 and sigma for
terminal atoms of 0.002
6. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
7. Others
 Fixed Sof: N2(0.6) H2C(0.6) H2D(0.6) C30(0.6) H30A(0.6) H30B(0.6) C29(0.6)
 H29A(0.6) H29B(0.6) C27(0.6) H27(0.6) C28(0.6) H28A(0.6) H28B(0.6) C23(0.4)
 H23A(0.4) H23B(0.4) C24(0.4) H24A(0.4) H24B(0.4) C25(0.4) H25A(0.4) H25B(0.4)
 N1(0.4) H1C(0.4) H1D(0.4) C22(0.4) H22(0.4)
8.a Ternary CH refined with riding coordinates:
 C27(H27), C22(H22)
8.b Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C7(H7A,H7B), C2(H2A,H2B), C1(H1A,H1B), N2(H2C,H2D), C30(H30A,
 H30B), C29(H29A,H29B), C28(H28A,H28B), C23(H23A,H23B), C24(H24A,H24B),
 C25(H25A,H25B), N1(H1C,H1D)
8.c Aromatic/amide H refined with riding coordinates:
 C4(H4A), C19(H19), C9(H9), C16(H16), C12(H12), C20(H20), C13(H13)
8.d Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C), C14(H14A,H14B,H14C)
8.e Idealised tetrahedral OH refined as rotating group:
 O6(H6), O2(H2), O4(H4)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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
O5 O 0.45334(13) 0.3887(5) 1.07358(10) 0.0353(8) Uani 1 1 d . U . . .
O8 O 0.44607(14) 0.7143(6) 0.18396(12) 0.0418(8) Uani 1 1 d . U . . .
O6 O 0.37024(12) 0.7925(5) 1.05967(12) 0.0330(7) Uani 1 1 d . U . . .
H6 H 0.401257 0.729959 1.092561 0.050 Uiso 1 1 calc GR . . . .
O3 O 0.45692(13) 0.3953(7) 0.39331(11) 0.0510(9) Uani 1 1 d . U . . .
O2 O 0.37841(17) -0.0405(6) 0.76010(12) 0.0507(9) Uani 1 1 d . U . . .
H2 H 0.379128 -0.094571 0.726788 0.076 Uiso 1 1 calc GR . . . .
O1 O 0.37116(17) -0.0366(6) 0.65077(13) 0.0544(9) Uani 1 1 d . U . . .
O4 O 0.37175(15) 0.7957(7) 0.34772(13) 0.0542(9) Uani 1 1 d . U . . .
H4 H 0.398754 0.724444 0.333572 0.081 Uiso 1 1 calc GR . . . .
O7 O 0.44961(15) 0.7463(8) 0.27832(13) 0.0619(10) Uani 1 1 d . U . . .
C4 C 0.37577(17) 0.3179(7) 0.70618(18) 0.0303(9) Uani 1 1 d . U . . .
H4A H 0.374552 0.490615 0.705645 0.036 Uiso 1 1 calc R . . . .
C8 C 0.3427(2) 0.3793(10) 0.48407(17) 0.0404(11) Uani 1 1 d . U . . .
C19 C 0.31139(18) 0.7264(8) 0.95014(16) 0.0301(9) Uani 1 1 d . U . . .
H19 H 0.285149 0.873684 0.946042 0.036 Uiso 1 1 calc R . . . .
C17 C 0.40358(18) 0.4478(8) 1.01383(15) 0.0288(9) Uani 1 1 d . U . . .
C10 C 0.40701(19) 0.4490(10) 0.41804(16) 0.0385(10) Uani 1 1 d . U . . .
C15 C 0.34212(18) 0.3784(8) 0.90240(16) 0.0283(9) Uani 1 1 d . U . . .
C18 C 0.36172(18) 0.6462(8) 1.00865(16) 0.0315(9) Uani 1 1 d . U . . .
C6 C 0.38583(19) 0.3286(8) 0.81687(15) 0.0295(9) Uani 1 1 d . U . . .
H6A H 0.376111 0.503452 0.806910 0.035 Uiso 1 1 calc R . . . .
H6B H 0.436425 0.312899 0.849024 0.035 Uiso 1 1 calc R . . . .
C21 C 0.50399(18) 0.1983(8) 1.07991(18) 0.0348(10) Uani 1 1 d . U . . .
H21A H 0.530788 0.235325 1.054175 0.052 Uiso 1 1 calc GR . . . .
H21B H 0.477633 0.044579 1.065975 0.052 Uiso 1 1 calc GR . . . .
H21C H 0.538391 0.184226 1.123924 0.052 Uiso 1 1 calc GR . . . .
C9 C 0.39645(18) 0.3129(9) 0.46326(15) 0.0325(10) Uani 1 1 d . U . . .
H9 H 0.425762 0.173460 0.480389 0.039 Uiso 1 1 calc R . . . .
C16 C 0.39363(18) 0.3023(9) 0.96092(16) 0.0336(10) Uani 1 1 d . U . . .
H16 H 0.421062 0.157702 0.965056 0.040 Uiso 1 1 calc R . . . .
C3 C 0.3739(2) 0.1939(8) 0.65362(17) 0.0350(9) Uani 1 1 d . U . . .
C7 C 0.33243(18) 0.2323(8) 0.84430(15) 0.0334(10) Uani 1 1 d . U . . .
H7A H 0.281567 0.247541 0.812608 0.040 Uiso 1 1 calc R . . . .
H7B H 0.342345 0.058306 0.855366 0.040 Uiso 1 1 calc R . . . .
C26 C 0.44068(18) 0.6317(7) 0.2297(2) 0.0360(9) Uani 1 1 d D U . . .
C12 C 0.3140(2) 0.7211(10) 0.41511(17) 0.0429(11) Uani 1 1 d . U . . .
H12 H 0.283589 0.857838 0.397442 0.051 Uiso 1 1 calc R . . . .
C20 C 0.30085(18) 0.5813(8) 0.89741(16) 0.0331(10) Uani 1 1 d . U . . .
H20 H 0.264359 0.625456 0.857651 0.040 Uiso 1 1 calc R . . . .
C2 C 0.3787(2) 0.3304(8) 0.59998(16) 0.0348(10) Uani 1 1 d . U . . .
H2A H 0.430322 0.331125 0.605869 0.042 Uiso 1 1 calc R . . . .
H2B H 0.364557 0.501337 0.602358 0.042 Uiso 1 1 calc R . . . .
C5 C 0.3794(2) 0.1963(8) 0.75922(17) 0.0327(9) Uani 1 1 d . U . . .
C14 C 0.50713(19) 0.1998(9) 0.42202(18) 0.0448(12) Uani 1 1 d . U . . .
H14A H 0.538444 0.175563 0.399603 0.067 Uiso 1 1 calc GR . . . .
H14B H 0.479806 0.050200 0.420136 0.067 Uiso 1 1 calc GR . . . .
H14C H 0.537339 0.240343 0.465885 0.067 Uiso 1 1 calc GR . . . .
C11 C 0.36615(19) 0.6594(9) 0.39378(16) 0.0402(10) Uani 1 1 d . U . . .
C13 C 0.3047(2) 0.5899(9) 0.46129(17) 0.0389(10) Uani 1 1 d . U . . .
H13 H 0.271361 0.646190 0.477678 0.047 Uiso 1 1 calc R . . . .
C1 C 0.33293(18) 0.2369(9) 0.53469(15) 0.0375(11) Uani 1 1 d . U . . .
H1A H 0.345882 0.064962 0.531905 0.045 Uiso 1 1 calc R . . . .
H1B H 0.280873 0.242026 0.527508 0.045 Uiso 1 1 calc R . . . .
N2 N 0.4174(3) 0.2345(11) 0.1854(2) 0.0295(6) Uani 0.6 1 d . U P A 1
H2C H 0.439368 0.086400 0.195075 0.035 Uiso 0.6 1 calc R . P A 1
H2D H 0.439885 0.323983 0.165791 0.035 Uiso 0.6 1 calc R . P A 1
C30 C 0.3361(3) 0.2052(16) 0.1428(3) 0.0430(19) Uani 0.6 1 d . U P A 1
H30A H 0.316446 0.350771 0.116330 0.052 Uiso 0.6 1 calc R . P A 1
H30B H 0.327116 0.059802 0.115715 0.052 Uiso 0.6 1 calc R . P A 1
C29 C 0.3047(3) 0.1767(13) 0.1896(3) 0.0402(16) Uani 0.6 1 d . U P A 1
H29A H 0.307924 0.004954 0.203148 0.048 Uiso 0.6 1 calc R . P A 1
H29B H 0.252780 0.226054 0.171343 0.048 Uiso 0.6 1 calc R . P A 1
C27 C 0.4224(3) 0.3613(12) 0.2437(3) 0.0370(6) Uani 0.6 1 d D U P A 1
H27 H 0.461890 0.292086 0.282183 0.044 Uiso 0.6 1 calc R . P A 1
C28 C 0.3492(3) 0.3407(16) 0.2455(3) 0.0463(16) Uani 0.6 1 d . U P A 1
H28A H 0.326051 0.502546 0.241112 0.056 Uiso 0.6 1 calc R . P A 1
H28B H 0.353332 0.266407 0.285372 0.056 Uiso 0.6 1 calc R . P A 1
C23 C 0.4176(5) 0.196(2) 0.2561(4) 0.0331(6) Uani 0.4 1 d . U P A 2
H23A H 0.442861 0.275144 0.297400 0.040 Uiso 0.4 1 calc R . P A 2
H23B H 0.440127 0.034372 0.257731 0.040 Uiso 0.4 1 calc R . P A 2
C24 C 0.3401(5) 0.167(2) 0.2419(5) 0.046(2) Uani 0.4 1 d . U P A 2
H24A H 0.330116 0.217511 0.278282 0.055 Uiso 0.4 1 calc R . P A 2
H24B H 0.325166 -0.004712 0.232055 0.055 Uiso 0.4 1 calc R . P A 2
C25 C 0.2989(5) 0.3270(18) 0.1861(4) 0.033(2) Uani 0.4 1 d . U P A 2
H25A H 0.296464 0.497580 0.198647 0.040 Uiso 0.4 1 calc R . P A 2
H25B H 0.248902 0.265677 0.161436 0.040 Uiso 0.4 1 calc R . P A 2
N1 N 0.3486(4) 0.300(2) 0.1495(4) 0.048(2) Uani 0.4 1 d . U P A 2
H1C H 0.338890 0.414959 0.119171 0.057 Uiso 0.4 1 calc R . P A 2
H1D H 0.345523 0.149164 0.132590 0.057 Uiso 0.4 1 calc R . P A 2
C22 C 0.4250(5) 0.3444(16) 0.2073(4) 0.0383(6) Uani 0.4 1 d D U P A 2
H22 H 0.465552 0.280702 0.197256 0.046 Uiso 0.4 1 calc R . 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
O5 C17 1.383(4) . ?
O5 C21 1.425(5) . ?
O8 C26 1.209(5) . ?
O6 H6 0.8400 . ?
O6 C18 1.390(5) . ?
O3 C10 1.380(5) . ?
O3 C14 1.439(5) . ?
O2 H2 0.8400 . ?
O2 C5 1.302(5) . ?
O1 C3 1.269(6) . ?
O4 H4 0.8400 . ?
O4 C11 1.355(5) . ?
O7 C26 1.246(6) . ?
C4 H4A 0.9500 . ?
C4 C3 1.393(6) . ?
C4 C5 1.385(6) . ?
C8 C9 1.403(6) . ?
C8 C13 1.370(7) . ?
C8 C1 1.499(6) . ?
C19 H19 0.9500 . ?
C19 C18 1.398(5) . ?
C19 C20 1.410(6) . ?
C17 C18 1.353(6) . ?
C17 C16 1.418(6) . ?
C10 C9 1.382(6) . ?
C10 C11 1.398(6) . ?
C15 C16 1.400(5) . ?
C15 C7 1.521(5) . ?
C15 C20 1.366(6) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C6 C7 1.552(5) . ?
C6 C5 1.491(5) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C9 H9 0.9500 . ?
C16 H16 0.9500 . ?
C3 C2 1.499(6) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C26 C27 1.597(8) . ?
C26 C22 1.654(9) . ?
C12 H12 0.9500 . ?
C12 C11 1.376(6) . ?
C12 C13 1.374(6) . ?
C20 H20 0.9500 . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C1 1.514(5) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C13 H13 0.9500 . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
N2 H2C 0.9100 . ?
N2 H2D 0.9100 . ?
N2 C30 1.534(7) . ?
N2 C27 1.498(9) . ?
C30 H30A 0.9900 . ?
C30 H30B 0.9900 . ?
C30 C29 1.479(11) . ?
C29 H29A 0.9900 . ?
C29 H29B 0.9900 . ?
C29 C28 1.538(9) . ?
C27 H27 1.0000 . ?
C27 C28 1.494(10) . ?
C28 H28A 0.9900 . ?
C28 H28B 0.9900 . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C23 C24 1.463(13) . ?
C23 C22 1.461(14) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C24 C25 1.509(14) . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
C25 N1 1.568(15) . ?
N1 H1C 0.9100 . ?
N1 H1D 0.9100 . ?
N1 C22 1.594(11) . ?
C22 H22 1.0000 . ?

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
C17 O5 C21 117.9(3) . . ?
C18 O6 H6 109.5 . . ?
C10 O3 C14 117.1(3) . . ?
C5 O2 H2 109.5 . . ?
C11 O4 H4 109.5 . . ?
C3 C4 H4A 119.1 . . ?
C5 C4 H4A 119.1 . . ?
C5 C4 C3 121.8(4) . . ?
C9 C8 C1 120.5(4) . . ?
C13 C8 C9 118.1(4) . . ?
C13 C8 C1 121.1(4) . . ?
C18 C19 H19 121.1 . . ?
C18 C19 C20 117.8(4) . . ?
C20 C19 H19 121.1 . . ?
O5 C17 C16 122.3(4) . . ?
C18 C17 O5 116.5(3) . . ?
C18 C17 C16 121.2(3) . . ?
O3 C10 C9 124.9(4) . . ?
O3 C10 C11 114.5(4) . . ?
C9 C10 C11 120.7(4) . . ?
C16 C15 C7 119.2(4) . . ?
C20 C15 C16 120.5(4) . . ?
C20 C15 C7 120.3(3) . . ?
O6 C18 C19 116.3(4) . . ?
C17 C18 O6 122.5(3) . . ?
C17 C18 C19 121.0(4) . . ?
H6A C6 H6B 107.8 . . ?
C7 C6 H6A 109.0 . . ?
C7 C6 H6B 109.0 . . ?
C5 C6 H6A 109.0 . . ?
C5 C6 H6B 109.0 . . ?
C5 C6 C7 112.9(3) . . ?
O5 C21 H21A 109.5 . . ?
O5 C21 H21B 109.5 . . ?
O5 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C8 C9 H9 119.8 . . ?
C10 C9 C8 120.5(4) . . ?
C10 C9 H9 119.8 . . ?
C17 C16 H16 121.0 . . ?
C15 C16 C17 117.9(4) . . ?
C15 C16 H16 121.0 . . ?
O1 C3 C4 121.3(4) . . ?
O1 C3 C2 118.2(4) . . ?
C4 C3 C2 120.4(4) . . ?
C15 C7 C6 109.4(3) . . ?
C15 C7 H7A 109.8 . . ?
C15 C7 H7B 109.8 . . ?
C6 C7 H7A 109.8 . . ?
C6 C7 H7B 109.8 . . ?
H7A C7 H7B 108.2 . . ?
O8 C26 O7 125.9(4) . . ?
O8 C26 C27 130.1(4) . . ?
O8 C26 C22 98.8(5) . . ?
O7 C26 C27 104.1(4) . . ?
O7 C26 C22 135.2(5) . . ?
C11 C12 H12 119.1 . . ?
C13 C12 H12 119.1 . . ?
C13 C12 C11 121.7(4) . . ?
C19 C20 H20 119.4 . . ?
C15 C20 C19 121.3(3) . . ?
C15 C20 H20 119.4 . . ?
C3 C2 H2A 108.1 . . ?
C3 C2 H2B 108.1 . . ?
C3 C2 C1 117.0(4) . . ?
H2A C2 H2B 107.3 . . ?
C1 C2 H2A 108.1 . . ?
C1 C2 H2B 108.1 . . ?
O2 C5 C4 120.1(4) . . ?
O2 C5 C6 118.0(4) . . ?
C4 C5 C6 121.9(4) . . ?
O3 C14 H14A 109.5 . . ?
O3 C14 H14B 109.5 . . ?
O3 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
O4 C11 C10 123.7(4) . . ?
O4 C11 C12 118.5(4) . . ?
C12 C11 C10 117.7(4) . . ?
C8 C13 C12 121.0(4) . . ?
C8 C13 H13 119.5 . . ?
C12 C13 H13 119.5 . . ?
C8 C1 C2 113.4(4) . . ?
C8 C1 H1A 108.9 . . ?
C8 C1 H1B 108.9 . . ?
C2 C1 H1A 108.9 . . ?
C2 C1 H1B 108.9 . . ?
H1A C1 H1B 107.7 . . ?
H2C N2 H2D 108.5 . . ?
C30 N2 H2C 110.3 . . ?
C30 N2 H2D 110.3 . . ?
C27 N2 H2C 110.3 . . ?
C27 N2 H2D 110.3 . . ?
C27 N2 C30 107.2(5) . . ?
N2 C30 H30A 111.5 . . ?
N2 C30 H30B 111.5 . . ?
H30A C30 H30B 109.3 . . ?
C29 C30 N2 101.2(5) . . ?
C29 C30 H30A 111.5 . . ?
C29 C30 H30B 111.5 . . ?
C30 C29 H29A 110.3 . . ?
C30 C29 H29B 110.3 . . ?
C30 C29 C28 107.0(6) . . ?
H29A C29 H29B 108.6 . . ?
C28 C29 H29A 110.3 . . ?
C28 C29 H29B 110.3 . . ?
C26 C27 H27 112.0 . . ?
N2 C27 C26 100.5(5) . . ?
N2 C27 H27 112.0 . . ?
C28 C27 C26 112.9(6) . . ?
C28 C27 N2 107.0(5) . . ?
C28 C27 H27 112.0 . . ?
C29 C28 H28A 110.8 . . ?
C29 C28 H28B 110.8 . . ?
C27 C28 C29 104.8(6) . . ?
C27 C28 H28A 110.8 . . ?
C27 C28 H28B 110.8 . . ?
H28A C28 H28B 108.9 . . ?
H23A C23 H23B 108.3 . . ?
C24 C23 H23A 109.9 . . ?
C24 C23 H23B 109.9 . . ?
C22 C23 H23A 109.9 . . ?
C22 C23 H23B 109.9 . . ?
C22 C23 C24 108.9(8) . . ?
C23 C24 H24A 110.4 . . ?
C23 C24 H24B 110.4 . . ?
C23 C24 C25 106.8(9) . . ?
H24A C24 H24B 108.6 . . ?
C25 C24 H24A 110.4 . . ?
C25 C24 H24B 110.4 . . ?
C24 C25 H25A 111.8 . . ?
C24 C25 H25B 111.8 . . ?
C24 C25 N1 99.8(8) . . ?
H25A C25 H25B 109.5 . . ?
N1 C25 H25A 111.8 . . ?
N1 C25 H25B 111.8 . . ?
C25 N1 H1C 112.3 . . ?
C25 N1 H1D 112.3 . . ?
C25 N1 C22 97.5(7) . . ?
H1C N1 H1D 109.9 . . ?
C22 N1 H1C 112.3 . . ?
C22 N1 H1D 112.3 . . ?
C26 C22 H22 110.0 . . ?
C23 C22 C26 110.7(8) . . ?
C23 C22 N1 101.9(8) . . ?
C23 C22 H22 110.0 . . ?
N1 C22 C26 114.1(7) . . ?
N1 C22 H22 110.0 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O5 C17 C18 O6 3.4(6) . . . . ?
O5 C17 C18 C19 177.9(4) . . . . ?
O5 C17 C16 C15 -179.7(4) . . . . ?
O8 C26 C27 N2 2.8(6) . . . . ?
O8 C26 C27 C28 -110.8(6) . . . . ?
O8 C26 C22 C23 178.7(6) . . . . ?
O8 C26 C22 N1 -67.1(8) . . . . ?
O3 C10 C9 C8 -178.2(4) . . . . ?
O3 C10 C11 O4 3.0(6) . . . . ?
O3 C10 C11 C12 178.4(3) . . . . ?
O1 C3 C2 C1 40.0(5) . . . . ?
O7 C26 C27 N2 -176.5(4) . . . . ?
O7 C26 C27 C28 69.9(5) . . . . ?
O7 C26 C22 C23 2.6(11) . . . . ?
O7 C26 C22 N1 116.8(7) . . . . ?
C4 C3 C2 C1 -142.9(4) . . . . ?
C18 C19 C20 C15 -4.7(6) . . . . ?
C18 C17 C16 C15 3.8(6) . . . . ?
C21 O5 C17 C18 -172.9(4) . . . . ?
C21 O5 C17 C16 10.5(5) . . . . ?
C9 C8 C13 C12 5.9(6) . . . . ?
C9 C8 C1 C2 90.1(5) . . . . ?
C9 C10 C11 O4 -177.3(4) . . . . ?
C9 C10 C11 C12 -1.9(6) . . . . ?
C16 C17 C18 O6 -179.9(4) . . . . ?
C16 C17 C18 C19 -5.4(6) . . . . ?
C16 C15 C7 C6 -88.9(4) . . . . ?
C16 C15 C20 C19 3.3(6) . . . . ?
C3 C4 C5 O2 -2.5(5) . . . . ?
C3 C4 C5 C6 176.4(3) . . . . ?
C3 C2 C1 C8 -178.3(4) . . . . ?
C7 C15 C16 C17 177.4(4) . . . . ?
C7 C15 C20 C19 -176.8(4) . . . . ?
C7 C6 C5 O2 -47.6(5) . . . . ?
C7 C6 C5 C4 133.5(4) . . . . ?
C26 C27 C28 C29 114.9(6) . . . . ?
C20 C19 C18 O6 -179.4(3) . . . . ?
C20 C19 C18 C17 5.7(6) . . . . ?
C20 C15 C16 C17 -2.7(6) . . . . ?
C20 C15 C7 C6 91.2(4) . . . . ?
C5 C4 C3 O1 4.1(6) . . . . ?
C5 C4 C3 C2 -172.9(3) . . . . ?
C5 C6 C7 C15 -179.5(3) . . . . ?
C14 O3 C10 C9 -7.6(6) . . . . ?
C14 O3 C10 C11 172.1(3) . . . . ?
C11 C10 C9 C8 2.2(6) . . . . ?
C11 C12 C13 C8 -5.9(6) . . . . ?
C13 C8 C9 C10 -4.1(6) . . . . ?
C13 C8 C1 C2 -83.5(5) . . . . ?
C13 C12 C11 O4 179.4(4) . . . . ?
C13 C12 C11 C10 3.7(6) . . . . ?
C1 C8 C9 C10 -177.9(4) . . . . ?
C1 C8 C13 C12 179.7(4) . . . . ?
N2 C30 C29 C28 35.5(7) . . . . ?
N2 C27 C28 C29 5.3(7) . . . . ?
C30 N2 C27 C26 -101.3(5) . . . . ?
C30 N2 C27 C28 16.7(7) . . . . ?
C30 C29 C28 C27 -26.4(8) . . . . ?
C27 N2 C30 C29 -32.3(7) . . . . ?
C23 C24 C25 N1 34.8(11) . . . . ?
C24 C23 C22 C26 96.9(9) . . . . ?
C24 C23 C22 N1 -24.7(11) . . . . ?
C24 C25 N1 C22 -47.3(9) . . . . ?
C25 N1 C22 C26 -74.9(9) . . . . ?
C25 N1 C22 C23 44.4(9) . . . . ?
C22 C23 C24 C25 -6.2(12) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.6350(16)
2 0.3650(16)

####################################################################### 
# 
# 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_mo_20240325_0m
_database_code_depnum_ccdc_archive 'CCDC 2334121'
loop_
_audit_author_name
_audit_author_address
'tian fanyu'
;Shanghai Institute of Materia Medica
China
;
_audit_update_record             
;
2024-02-21 deposited with the CCDC.	2024-04-24 downloaded from the CCDC.
;
_audit_creation_date             2024-02-21
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C5 H11 N O2, C21 H24 O6'
_chemical_formula_sum            'C26 H35 N O8'
_chemical_formula_weight         489.55
_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/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   15.254(3)
_cell_length_b                   7.9952(14)
_cell_length_c                   20.500(3)
_cell_angle_alpha                90
_cell_angle_beta                 96.512(5)
_cell_angle_gamma                90
_cell_volume                     2484.0(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4171
_cell_measurement_temperature    170
_cell_measurement_theta_max      22.807
_cell_measurement_theta_min      2.280
_shelx_estimated_absorpt_T_max   0.994
_shelx_estimated_absorpt_T_min   0.988
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.4469
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1305 before and 0.0774 after correction. The Ratio of minimum to maximum transmission is 0.5995. 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    1.309
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1048
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.06
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0955
_diffrn_reflns_av_unetI/netI     0.1102
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            17294
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.413
_diffrn_reflns_theta_min         2.000
_diffrn_ambient_temperature      170.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2752
_reflns_number_total             5068
_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 V8.40A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.423
_refine_diff_density_min         -0.322
_refine_diff_density_rms         0.070
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     324
_refine_ls_number_reflns         5068
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1791
_refine_ls_R_factor_gt           0.0871
_refine_ls_restrained_S_all      1.039
_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)+(0.0455P)²+5.8189P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1623
_refine_ls_wR_factor_ref         0.2048
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C2(H2a,H2b), C24(H24a,H24b), C7(H7a,H7b), C1(H1a,H1b), C6(H6a,H6b)
2.b Aromatic/amide H refined with riding coordinates:
 C12(H12), C4(H4a), C13(H13), C20(H20), C9(H9), C19(H19), C16(H16)
2.c Idealised Me refined as rotating group:
 C25(H25a,H25b,H25c), C14(H14a,H14b,H14c), C23(H23a,H23b,H23c), C21(H21a,H21b,
 H21c), C22(H22a,H22b,H22c)
2.d Idealised tetrahedral OH refined as rotating group:
 O4(H4), O6(H6), O1(H1)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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
O7 O 0.1284(2) 0.6067(4) 0.63210(14) 0.0405(8) Uani 1 1 d . . . . .
O3 O 0.77246(19) 1.2409(4) 0.47615(13) 0.0384(8) Uani 1 1 d . . . . .
O4 O 0.7326(2) 1.1760(4) 0.34878(13) 0.0412(8) Uani 1 1 d . . . . .
H4 H 0.774755 1.230189 0.368490 0.062 Uiso 1 1 calc GR . . . .
O5 O 0.0958(2) 0.7055(4) 0.80729(14) 0.0405(8) Uani 1 1 d . . . . .
O6 O 0.0391(2) 0.4289(4) 0.85460(16) 0.0433(8) Uani 1 1 d . . . . .
H6 H 0.028030 0.335489 0.870502 0.065 Uiso 1 1 calc GR . . . .
O8 O -0.0100(2) 0.6488(4) 0.58588(15) 0.0492(9) Uani 1 1 d . . . . .
O1 O 0.6304(2) 0.4133(4) 0.62297(17) 0.0505(9) Uani 1 1 d . . . . .
H1 H 0.611572 0.367428 0.655510 0.076 Uiso 1 1 calc GR . . . .
O2 O 0.5288(2) 0.3553(4) 0.70763(15) 0.0483(9) Uani 1 1 d . . . . .
N1 N 0.1198(2) 0.2630(4) 0.58792(16) 0.0301(8) Uani 1 1 d . . . . .
C17 C 0.1530(3) 0.5722(5) 0.80919(19) 0.0307(10) Uani 1 1 d . . . . .
C12 C 0.6238(3) 0.9783(6) 0.3726(2) 0.0389(11) Uani 1 1 d . . . . .
H12 H 0.607274 0.961804 0.326984 0.047 Uiso 1 1 calc R . . . .
C11 C 0.6890(3) 1.0922(5) 0.3936(2) 0.0353(10) Uani 1 1 d . . . . .
C8 C 0.6051(3) 0.9072(6) 0.4843(2) 0.0366(11) Uani 1 1 d . . . . .
C10 C 0.7102(3) 1.1189(5) 0.4614(2) 0.0334(10) Uani 1 1 d . . . . .
C4 C 0.4989(3) 0.5636(6) 0.6276(2) 0.0342(10) Uani 1 1 d . . . . .
H4A H 0.460157 0.650105 0.610611 0.041 Uiso 1 1 calc R . . . .
C13 C 0.5826(3) 0.8884(6) 0.4180(2) 0.0401(11) Uani 1 1 d . . . . .
H13 H 0.537367 0.811337 0.402843 0.048 Uiso 1 1 calc R . . . .
C5 C 0.4771(3) 0.4650(6) 0.6816(2) 0.0369(11) Uani 1 1 d . . . . .
C15 C 0.2906(3) 0.4350(6) 0.79440(19) 0.0353(11) Uani 1 1 d . . . . .
C18 C 0.1209(3) 0.4258(5) 0.8348(2) 0.0321(10) Uani 1 1 d . . . . .
C20 C 0.2573(3) 0.2888(6) 0.8174(2) 0.0360(11) Uani 1 1 d . . . . .
H20 H 0.291856 0.189716 0.819078 0.043 Uiso 1 1 calc R . . . .
C9 C 0.6692(3) 1.0240(5) 0.5057(2) 0.0353(10) Uani 1 1 d . . . . .
H9 H 0.685209 1.039319 0.551456 0.042 Uiso 1 1 calc R . . . .
C2 C 0.6072(3) 0.6319(6) 0.5455(2) 0.0378(11) Uani 1 1 d . . . . .
H2A H 0.597557 0.564722 0.504769 0.045 Uiso 1 1 calc R . . . .
H2B H 0.671534 0.649623 0.555607 0.045 Uiso 1 1 calc R . . . .
C26 C 0.0574(3) 0.5613(6) 0.6018(2) 0.0362(11) Uani 1 1 d . . . . .
C24 C 0.0427(3) 0.3807(5) 0.5788(2) 0.0331(10) Uani 1 1 d . . . . .
H24A H -0.005014 0.332896 0.602002 0.040 Uiso 1 1 calc R . . . .
H24B H 0.020834 0.383066 0.531433 0.040 Uiso 1 1 calc R . . . .
C19 C 0.1735(3) 0.2846(5) 0.8384(2) 0.0353(11) Uani 1 1 d . . . . .
H19 H 0.152292 0.183569 0.855250 0.042 Uiso 1 1 calc R . . . .
C7 C 0.3831(3) 0.4409(7) 0.7750(2) 0.0444(12) Uani 1 1 d . . . . .
H7A H 0.418070 0.522040 0.803756 0.053 Uiso 1 1 calc R . . . .
H7B H 0.410662 0.329532 0.782921 0.053 Uiso 1 1 calc R . . . .
C25 C 0.1956(3) 0.3286(6) 0.5554(2) 0.0362(11) Uani 1 1 d . . . . .
H25A H 0.177307 0.343111 0.508304 0.054 Uiso 1 1 calc GR . . . .
H25B H 0.244730 0.249123 0.561596 0.054 Uiso 1 1 calc GR . . . .
H25C H 0.214399 0.436543 0.574795 0.054 Uiso 1 1 calc GR . . . .
C14 C 0.8046(3) 1.2632(6) 0.5440(2) 0.0441(12) Uani 1 1 d . . . . .
H14A H 0.845040 1.358803 0.548659 0.066 Uiso 1 1 calc GR . . . .
H14B H 0.835974 1.162041 0.560558 0.066 Uiso 1 1 calc GR . . . .
H14C H 0.754876 1.283862 0.569273 0.066 Uiso 1 1 calc GR . . . .
C23 C 0.0900(3) 0.1011(6) 0.5556(2) 0.0409(11) Uani 1 1 d . . . . .
H23A H 0.037383 0.060875 0.574106 0.061 Uiso 1 1 calc GR . . . .
H23B H 0.137226 0.017965 0.563415 0.061 Uiso 1 1 calc GR . . . .
H23C H 0.075966 0.118876 0.508304 0.061 Uiso 1 1 calc GR . . . .
C16 C 0.2368(3) 0.5779(5) 0.7899(2) 0.0333(10) Uani 1 1 d . . . . .
H16 H 0.258306 0.679404 0.773593 0.040 Uiso 1 1 calc R . . . .
C21 C 0.1207(3) 0.8537(6) 0.7756(2) 0.0456(12) Uani 1 1 d . . . . .
H21A H 0.132699 0.826926 0.730832 0.068 Uiso 1 1 calc GR . . . .
H21B H 0.173953 0.900644 0.800173 0.068 Uiso 1 1 calc GR . . . .
H21C H 0.072723 0.935534 0.774081 0.068 Uiso 1 1 calc GR . . . .
C22 C 0.1467(3) 0.2310(6) 0.6596(2) 0.0416(12) Uani 1 1 d . . . . .
H22A H 0.167142 0.335627 0.681171 0.062 Uiso 1 1 calc GR . . . .
H22B H 0.194404 0.148397 0.664608 0.062 Uiso 1 1 calc GR . . . .
H22C H 0.095976 0.188256 0.679907 0.062 Uiso 1 1 calc GR . . . .
C3 C 0.5749(3) 0.5344(6) 0.6003(2) 0.0358(11) Uani 1 1 d . . . . .
C1 C 0.5627(3) 0.8009(6) 0.5331(2) 0.0430(12) Uani 1 1 d . . . . .
H1A H 0.499917 0.783020 0.516593 0.052 Uiso 1 1 calc R . . . .
H1B H 0.564877 0.862276 0.575222 0.052 Uiso 1 1 calc R . . . .
C6 C 0.3882(3) 0.4885(7) 0.7054(2) 0.0436(12) Uani 1 1 d . . . . .
H6A H 0.371107 0.607585 0.699807 0.052 Uiso 1 1 calc R . . . .
H6B H 0.344330 0.421575 0.677252 0.052 Uiso 1 1 calc R . . . .


_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
O7 C26 1.239(5) . ?
O3 C10 1.371(5) . ?
O3 C14 1.433(5) . ?
O4 H4 0.8400 . ?
O4 C11 1.368(5) . ?
O5 C17 1.375(5) . ?
O5 C21 1.423(5) . ?
O6 H6 0.8400 . ?
O6 C18 1.355(5) . ?
O8 C26 1.256(5) . ?
O1 H1 0.8400 . ?
O1 C3 1.334(5) . ?
O2 C5 1.257(5) . ?
N1 C24 1.502(5) . ?
N1 C25 1.494(5) . ?
N1 C23 1.500(5) . ?
N1 C22 1.503(5) . ?
C17 C18 1.394(6) . ?
C17 C16 1.382(6) . ?
C12 H12 0.9500 . ?
C12 C11 1.381(6) . ?
C12 C13 1.383(6) . ?
C11 C10 1.407(6) . ?
C8 C13 1.372(6) . ?
C8 C9 1.387(6) . ?
C8 C1 1.513(6) . ?
C10 C9 1.386(6) . ?
C4 H4A 0.9500 . ?
C4 C5 1.428(6) . ?
C4 C3 1.364(6) . ?
C13 H13 0.9500 . ?
C5 C6 1.505(6) . ?
C15 C20 1.379(6) . ?
C15 C7 1.511(6) . ?
C15 C16 1.403(6) . ?
C18 C19 1.382(6) . ?
C20 H20 0.9500 . ?
C20 C19 1.394(6) . ?
C9 H9 0.9500 . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C3 1.496(6) . ?
C2 C1 1.520(6) . ?
C26 C24 1.528(6) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C19 H19 0.9500 . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C6 1.487(6) . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C16 H16 0.9500 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?

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 O3 C14 117.1(3) . . ?
C11 O4 H4 109.5 . . ?
C17 O5 C21 117.2(3) . . ?
C18 O6 H6 109.5 . . ?
C3 O1 H1 109.5 . . ?
C24 N1 C22 110.6(3) . . ?
C25 N1 C24 111.0(3) . . ?
C25 N1 C23 108.5(3) . . ?
C25 N1 C22 111.0(3) . . ?
C23 N1 C24 107.0(3) . . ?
C23 N1 C22 108.7(3) . . ?
O5 C17 C18 114.4(4) . . ?
O5 C17 C16 124.8(4) . . ?
C16 C17 C18 120.7(4) . . ?
C11 C12 H12 120.0 . . ?
C11 C12 C13 120.0(4) . . ?
C13 C12 H12 120.0 . . ?
O4 C11 C12 120.1(4) . . ?
O4 C11 C10 120.9(4) . . ?
C12 C11 C10 119.0(4) . . ?
C13 C8 C9 118.4(4) . . ?
C13 C8 C1 121.1(4) . . ?
C9 C8 C1 120.5(4) . . ?
O3 C10 C11 113.7(4) . . ?
O3 C10 C9 126.7(4) . . ?
C9 C10 C11 119.6(4) . . ?
C5 C4 H4A 119.8 . . ?
C3 C4 H4A 119.8 . . ?
C3 C4 C5 120.5(4) . . ?
C12 C13 H13 119.1 . . ?
C8 C13 C12 121.8(4) . . ?
C8 C13 H13 119.1 . . ?
O2 C5 C4 121.6(4) . . ?
O2 C5 C6 119.7(4) . . ?
C4 C5 C6 118.7(4) . . ?
C20 C15 C7 120.6(4) . . ?
C20 C15 C16 118.5(4) . . ?
C16 C15 C7 120.9(4) . . ?
O6 C18 C17 118.1(4) . . ?
O6 C18 C19 123.2(4) . . ?
C19 C18 C17 118.7(4) . . ?
C15 C20 H20 119.6 . . ?
C15 C20 C19 120.8(4) . . ?
C19 C20 H20 119.6 . . ?
C8 C9 H9 119.5 . . ?
C10 C9 C8 121.0(4) . . ?
C10 C9 H9 119.5 . . ?
H2A C2 H2B 107.6 . . ?
C3 C2 H2A 108.7 . . ?
C3 C2 H2B 108.7 . . ?
C3 C2 C1 114.2(4) . . ?
C1 C2 H2A 108.7 . . ?
C1 C2 H2B 108.7 . . ?
O7 C26 O8 127.6(4) . . ?
O7 C26 C24 121.4(4) . . ?
O8 C26 C24 111.0(4) . . ?
N1 C24 C26 117.9(4) . . ?
N1 C24 H24A 107.8 . . ?
N1 C24 H24B 107.8 . . ?
C26 C24 H24A 107.8 . . ?
C26 C24 H24B 107.8 . . ?
H24A C24 H24B 107.2 . . ?
C18 C19 C20 120.7(4) . . ?
C18 C19 H19 119.6 . . ?
C20 C19 H19 119.6 . . ?
C15 C7 H7A 108.7 . . ?
C15 C7 H7B 108.7 . . ?
H7A C7 H7B 107.6 . . ?
C6 C7 C15 114.3(4) . . ?
C6 C7 H7A 108.7 . . ?
C6 C7 H7B 108.7 . . ?
N1 C25 H25A 109.5 . . ?
N1 C25 H25B 109.5 . . ?
N1 C25 H25C 109.5 . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
O3 C14 H14A 109.5 . . ?
O3 C14 H14B 109.5 . . ?
O3 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
N1 C23 H23A 109.5 . . ?
N1 C23 H23B 109.5 . . ?
N1 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C17 C16 C15 120.5(4) . . ?
C17 C16 H16 119.8 . . ?
C15 C16 H16 119.8 . . ?
O5 C21 H21A 109.5 . . ?
O5 C21 H21B 109.5 . . ?
O5 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
N1 C22 H22A 109.5 . . ?
N1 C22 H22B 109.5 . . ?
N1 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
O1 C3 C4 121.1(4) . . ?
O1 C3 C2 113.0(4) . . ?
C4 C3 C2 125.9(4) . . ?
C8 C1 C2 113.2(4) . . ?
C8 C1 H1A 108.9 . . ?
C8 C1 H1B 108.9 . . ?
C2 C1 H1A 108.9 . . ?
C2 C1 H1B 108.9 . . ?
H1A C1 H1B 107.8 . . ?
C5 C6 H6A 108.5 . . ?
C5 C6 H6B 108.5 . . ?
C7 C6 C5 115.2(4) . . ?
C7 C6 H6A 108.5 . . ?
C7 C6 H6B 108.5 . . ?
H6A C6 H6B 107.5 . . ?

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
O7 C26 C24 N1 -6.0(6) . . . . ?
O3 C10 C9 C8 178.1(4) . . . . ?
O4 C11 C10 O3 4.0(6) . . . . ?
O4 C11 C10 C9 -175.7(4) . . . . ?
O5 C17 C18 O6 0.1(5) . . . . ?
O5 C17 C18 C19 179.6(4) . . . . ?
O5 C17 C16 C15 179.4(4) . . . . ?
O6 C18 C19 C20 -179.8(4) . . . . ?
O8 C26 C24 N1 174.0(3) . . . . ?
O2 C5 C6 C7 27.4(7) . . . . ?
C17 C18 C19 C20 0.7(6) . . . . ?
C12 C11 C10 O3 -176.7(4) . . . . ?
C12 C11 C10 C9 3.7(6) . . . . ?
C11 C12 C13 C8 -0.7(7) . . . . ?
C11 C10 C9 C8 -2.3(6) . . . . ?
C4 C5 C6 C7 -155.5(4) . . . . ?
C13 C12 C11 O4 177.1(4) . . . . ?
C13 C12 C11 C10 -2.2(6) . . . . ?
C13 C8 C9 C10 -0.5(6) . . . . ?
C13 C8 C1 C2 84.3(5) . . . . ?
C5 C4 C3 O1 0.3(7) . . . . ?
C5 C4 C3 C2 -177.6(4) . . . . ?
C15 C20 C19 C18 1.8(6) . . . . ?
C15 C7 C6 C5 -169.3(4) . . . . ?
C18 C17 C16 C15 1.5(6) . . . . ?
C20 C15 C7 C6 120.4(5) . . . . ?
C20 C15 C16 C17 0.9(6) . . . . ?
C9 C8 C13 C12 2.1(7) . . . . ?
C9 C8 C1 C2 -94.4(5) . . . . ?
C7 C15 C20 C19 176.9(4) . . . . ?
C7 C15 C16 C17 -178.5(4) . . . . ?
C25 N1 C24 C26 -56.5(5) . . . . ?
C14 O3 C10 C11 -173.5(4) . . . . ?
C14 O3 C10 C9 6.2(6) . . . . ?
C23 N1 C24 C26 -174.6(4) . . . . ?
C16 C17 C18 O6 178.1(4) . . . . ?
C16 C17 C18 C19 -2.3(6) . . . . ?
C16 C15 C20 C19 -2.6(6) . . . . ?
C16 C15 C7 C6 -60.1(6) . . . . ?
C21 O5 C17 C18 -173.8(4) . . . . ?
C21 O5 C17 C16 8.3(6) . . . . ?
C22 N1 C24 C26 67.2(5) . . . . ?
C3 C4 C5 O2 3.7(7) . . . . ?
C3 C4 C5 C6 -173.3(4) . . . . ?
C3 C2 C1 C8 171.9(4) . . . . ?
C1 C8 C13 C12 -176.7(4) . . . . ?
C1 C8 C9 C10 178.2(4) . . . . ?
C1 C2 C3 O1 -161.5(4) . . . . ?
C1 C2 C3 C4 16.5(7) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
