# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2022

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

data_cu_20210409THZ_TBUDH_0m
_database_code_depnum_ccdc_archive 'CCDC 2153627'
loop_
_audit_author_name
_audit_author_address
Tianhengzhi
;Fudan University
China
;
_audit_update_record             
;
2022-02-21 deposited with the CCDC.	2022-05-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C32 H39 N3 O8'
_chemical_formula_weight         593.66

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   12.891(6)
_cell_length_b                   8.629(5)
_cell_length_c                   15.510(7)
_cell_angle_alpha                90
_cell_angle_beta                 111.57(2)
_cell_angle_gamma                90
_cell_volume                     1604.5(14)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    9976
_cell_measurement_theta_min      3.07
_cell_measurement_theta_max      65.12

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.229
_exptl_crystal_F_000             632
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.730
_shelx_estimated_absorpt_T_min   0.868
_shelx_estimated_absorpt_T_max   0.931
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6068
_exptl_absorpt_correction_T_max  0.7526
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'D8 Venture'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            19779
_diffrn_reflns_av_unetI/netI     0.0713
_diffrn_reflns_av_R_equivalents  0.0869
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.687
_diffrn_reflns_theta_max         65.009
_diffrn_reflns_theta_full        65.009
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_point_group_measured_fraction_full 0.984
_reflns_number_total             5367
_reflns_number_gt                4848
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.835
_reflns_Friedel_fraction_max     0.968
_reflns_Friedel_fraction_full    0.968

_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.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0338P)²+0.1266P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1995 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.14(11)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         5367
_refine_ls_number_parameters     398
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0474
_refine_ls_R_factor_gt           0.0332
_refine_ls_wR_factor_ref         0.0836
_refine_ls_wR_factor_gt          0.0803
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_restrained_S_all      1.062
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 0.62030(14) 0.6786(2) 0.73894(16) 0.0405(5) Uani 1 1 d . . . . .
O2 O 0.67602(15) 0.4483(2) 0.70254(19) 0.0513(6) Uani 1 1 d . . . . .
O3 O 0.41182(13) 0.7169(2) 0.71390(15) 0.0376(5) Uani 1 1 d . . . . .
O4 O 0.13777(13) 0.8289(2) 0.42738(13) 0.0316(4) Uani 1 1 d . . . . .
O5 O 0.16357(14) 0.6799(2) 0.31886(13) 0.0294(4) Uani 1 1 d . . . . .
O6 O 0.05919(15) 0.4687(2) 0.43483(13) 0.0392(5) Uani 1 1 d . . . . .
O7 O 0.38507(13) 0.3493(2) 0.81604(13) 0.0311(4) Uani 1 1 d . . . . .
O8 O 0.21148(15) 0.2570(2) 0.78890(15) 0.0376(5) Uani 1 1 d . . . . .
N1 N 0.11709(15) 0.5071(3) 0.67491(15) 0.0280(5) Uani 1 1 d . . . . .
N2 N 0.49214(15) 0.4978(2) 0.67333(16) 0.0271(5) Uani 1 1 d . . . . .
N3 N 0.07202(17) 0.4468(3) 0.58405(16) 0.0301(5) Uani 1 1 d . . . . .
H39 H 0.007(3) 0.401(4) 0.570(2) 0.045 Uiso 1 1 d . U . . .
C1 C 0.1479(2) 0.8337(4) 0.9558(2) 0.0426(7) Uani 1 1 d . . . . .
H1 H 0.163651 0.871847 1.015355 0.051 Uiso 1 1 calc R U . . .
C2 C 0.1405(2) 0.9333(4) 0.8843(2) 0.0420(7) Uani 1 1 d . . . . .
H19 H 0.151128 1.039067 0.895818 0.050 Uiso 1 1 calc R U . . .
C3 C 0.1174(2) 0.8773(3) 0.7957(2) 0.0377(6) Uani 1 1 d . . . . .
H18 H 0.113081 0.945583 0.748080 0.045 Uiso 1 1 calc R U . . .
C4 C 0.10067(18) 0.7195(3) 0.77714(19) 0.0295(5) Uani 1 1 d . . . . .
C5 C 0.0709(2) 0.6625(3) 0.67938(19) 0.0335(6) Uani 1 1 d . . . . .
H17 H -0.009701 0.658862 0.649361 0.040 Uiso 1 1 calc R U . . .
H22 H 0.098770 0.735440 0.645471 0.040 Uiso 1 1 calc R U . . .
C6 C 0.23861(17) 0.4928(3) 0.71385(17) 0.0236(5) Uani 1 1 d . . . . .
H23 H 0.266702 0.583049 0.754040 0.028 Uiso 1 1 calc R U . . .
C7 C 0.29584(18) 0.4962(3) 0.64031(18) 0.0245(5) Uani 1 1 d . . . . .
C8 C 0.40512(18) 0.5890(3) 0.68176(19) 0.0260(5) Uani 1 1 d . . . . .
C9 C 0.60605(19) 0.5365(3) 0.7062(2) 0.0305(6) Uani 1 1 d . . . . .
C10 C 0.7315(2) 0.7525(3) 0.7761(2) 0.0399(7) Uani 1 1 d . . . . .
C11 C 0.7027(3) 0.9112(4) 0.8016(4) 0.0699(13) Uani 1 1 d . . . . .
H37 H 0.654717 0.963298 0.746768 0.105 Uiso 1 1 calc R U . . .
H38 H 0.769849 0.970293 0.829711 0.105 Uiso 1 1 calc R U . . .
H2 H 0.665251 0.900975 0.844576 0.105 Uiso 1 1 calc R U . . .
C12 C 0.8055(3) 0.6644(4) 0.8608(3) 0.0594(10) Uani 1 1 d . . . . .
H3 H 0.768606 0.655154 0.904228 0.089 Uiso 1 1 calc R U . . .
H4 H 0.874560 0.719195 0.889275 0.089 Uiso 1 1 calc R U . . .
H5 H 0.820337 0.562946 0.842668 0.089 Uiso 1 1 calc R U . . .
C13 C 0.7801(3) 0.7584(5) 0.7015(3) 0.0606(10) Uani 1 1 d . . . . .
H8 H 0.795133 0.654964 0.686450 0.091 Uiso 1 1 calc R U . . .
H6 H 0.848295 0.816782 0.723239 0.091 Uiso 1 1 calc R U . . .
H7 H 0.727988 0.807188 0.647234 0.091 Uiso 1 1 calc R U . . .
C14 C 0.21714(17) 0.5858(3) 0.55486(17) 0.0236(5) Uani 1 1 d . . . . .
H9 H 0.202564 0.687556 0.576080 0.028 Uiso 1 1 calc R U . . .
C15 C 0.26083(19) 0.6118(3) 0.47710(19) 0.0269(5) Uani 1 1 d . . . . .
H10 H 0.334307 0.658720 0.501715 0.032 Uiso 1 1 calc R U . . .
H16 H 0.266758 0.513549 0.448888 0.032 Uiso 1 1 calc R U . . .
C16 C 0.18034(18) 0.7180(3) 0.40518(18) 0.0248(5) Uani 1 1 d . . . . .
C17 C 0.0815(2) 0.7777(3) 0.2492(2) 0.0329(6) Uani 1 1 d . . . . .
H15 H 0.102078 0.886039 0.260239 0.040 Uiso 1 1 calc R U . . .
H11 H 0.008114 0.763861 0.251983 0.040 Uiso 1 1 calc R U . . .
C18 C 0.0810(2) 0.7283(4) 0.1563(2) 0.0415(7) Uani 1 1 d . . . . .
H12 H 0.154199 0.741398 0.154722 0.062 Uiso 1 1 calc R U . . .
H14 H 0.028718 0.790637 0.108719 0.062 Uiso 1 1 calc R U . . .
H13 H 0.059589 0.621310 0.145926 0.062 Uiso 1 1 calc R U . . .
C19 C 0.10642(18) 0.4977(3) 0.51716(18) 0.0271(5) Uani 1 1 d . . . . .
C20 C 0.1317(2) 0.6764(4) 0.9382(2) 0.0390(6) Uani 1 1 d . . . . .
H20 H 0.136547 0.608811 0.986269 0.047 Uiso 1 1 calc R U . . .
C21 C 0.1082(2) 0.6190(3) 0.8497(2) 0.0321(6) Uani 1 1 d . . . . .
H21 H 0.097527 0.513157 0.838614 0.039 Uiso 1 1 calc R U . . .
C22 C 0.27346(19) 0.3495(3) 0.77636(18) 0.0269(5) Uani 1 1 d . . . . .
C23 C 0.4455(2) 0.2206(3) 0.8784(2) 0.0385(7) Uani 1 1 d . . . . .
C24 C 0.4174(3) 0.2226(5) 0.9647(2) 0.0559(9) Uani 1 1 d . . . . .
H25 H 0.424537 0.326302 0.988681 0.084 Uiso 1 1 calc R U . . .
H24 H 0.467519 0.155451 1.010575 0.084 Uiso 1 1 calc R U . . .
H26 H 0.342110 0.187428 0.949821 0.084 Uiso 1 1 calc R U . . .
C25 C 0.4186(3) 0.0674(3) 0.8266(3) 0.0456(8) Uani 1 1 d . . . . .
H29 H 0.341959 0.041125 0.813680 0.068 Uiso 1 1 calc R U . . .
H28 H 0.465890 -0.012361 0.863982 0.068 Uiso 1 1 calc R U . . .
H27 H 0.430877 0.076567 0.769406 0.068 Uiso 1 1 calc R U . . .
C26 C 0.5670(2) 0.2650(4) 0.9001(3) 0.0564(10) Uani 1 1 d . . . . .
H31 H 0.581913 0.265808 0.843803 0.085 Uiso 1 1 calc R U . . .
H30 H 0.614905 0.190999 0.942389 0.085 Uiso 1 1 calc R U . . .
H32 H 0.580794 0.366210 0.927692 0.085 Uiso 1 1 calc R U . . .
C27 C 0.33475(19) 0.3436(3) 0.61463(18) 0.0258(5) Uani 1 1 d . . . . .
C28 C 0.44917(19) 0.3504(3) 0.63281(19) 0.0273(5) Uani 1 1 d . . . . .
C29 C 0.5058(2) 0.2283(3) 0.6124(2) 0.0373(6) Uani 1 1 d . . . . .
H33 H 0.582004 0.233918 0.624990 0.045 Uiso 1 1 calc R U . . .
C30 C 0.4444(3) 0.0963(4) 0.5724(2) 0.0452(8) Uani 1 1 d . . . . .
H34 H 0.480229 0.013025 0.557246 0.054 Uiso 1 1 calc R U . . .
C31 C 0.3314(3) 0.0871(3) 0.5548(2) 0.0424(7) Uani 1 1 d . . . . .
H35 H 0.292442 -0.002586 0.528803 0.051 Uiso 1 1 calc R U . . .
C32 C 0.2758(2) 0.2105(3) 0.57556(19) 0.0326(6) Uani 1 1 d . . . . .
H36 H 0.199735 0.204062 0.563439 0.039 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C9 1.314(3) . ?
O1 C10 1.479(3) . ?
O2 C9 1.197(3) . ?
O3 C8 1.201(3) . ?
O4 C16 1.214(3) . ?
O5 C16 1.317(3) . ?
O5 C17 1.469(3) . ?
O6 C19 1.222(3) . ?
O7 C22 1.341(3) . ?
O7 C23 1.491(3) . ?
O8 C22 1.195(3) . ?
N1 N3 1.412(3) . ?
N1 C6 1.462(3) . ?
N1 C5 1.480(4) . ?
N2 C9 1.406(3) . ?
N2 C8 1.415(3) . ?
N2 C28 1.437(3) . ?
N3 C19 1.343(3) . ?
N3 H39 0.88(4) . ?
C1 C2 1.378(5) . ?
C1 C20 1.386(5) . ?
C1 H1 0.9300 . ?
C2 C3 1.383(5) . ?
C2 H19 0.9300 . ?
C3 C4 1.392(4) . ?
C3 H18 0.9300 . ?
C4 C21 1.396(4) . ?
C4 C5 1.503(4) . ?
C5 H17 0.9700 . ?
C5 H22 0.9700 . ?
C6 C22 1.533(4) . ?
C6 C7 1.570(4) . ?
C6 H23 0.9800 . ?
C7 C27 1.514(3) . ?
C7 C8 1.540(3) . ?
C7 C14 1.547(3) . ?
C10 C13 1.506(5) . ?
C10 C11 1.509(5) . ?
C10 C12 1.514(5) . ?
C11 H37 0.9600 . ?
C11 H38 0.9600 . ?
C11 H2 0.9600 . ?
C12 H3 0.9600 . ?
C12 H4 0.9600 . ?
C12 H5 0.9600 . ?
C13 H8 0.9600 . ?
C13 H6 0.9600 . ?
C13 H7 0.9600 . ?
C14 C15 1.524(4) . ?
C14 C19 1.531(3) . ?
C14 H9 0.9800 . ?
C15 C16 1.520(4) . ?
C15 H10 0.9700 . ?
C15 H16 0.9700 . ?
C17 C18 1.501(4) . ?
C17 H15 0.9700 . ?
C17 H11 0.9700 . ?
C18 H12 0.9600 . ?
C18 H14 0.9600 . ?
C18 H13 0.9600 . ?
C20 C21 1.384(4) . ?
C20 H20 0.9300 . ?
C21 H21 0.9300 . ?
C23 C24 1.511(5) . ?
C23 C25 1.519(5) . ?
C23 C26 1.525(4) . ?
C24 H25 0.9600 . ?
C24 H24 0.9600 . ?
C24 H26 0.9600 . ?
C25 H29 0.9600 . ?
C25 H28 0.9600 . ?
C25 H27 0.9600 . ?
C26 H31 0.9600 . ?
C26 H30 0.9600 . ?
C26 H32 0.9600 . ?
C27 C32 1.388(4) . ?
C27 C28 1.397(3) . ?
C28 C29 1.383(4) . ?
C29 C30 1.395(4) . ?
C29 H33 0.9300 . ?
C30 C31 1.382(5) . ?
C30 H34 0.9300 . ?
C31 C32 1.386(4) . ?
C31 H35 0.9300 . ?
C32 H36 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C9 O1 C10 122.1(2) . . ?
C16 O5 C17 114.16(19) . . ?
C22 O7 C23 121.0(2) . . ?
N3 N1 C6 111.49(19) . . ?
N3 N1 C5 110.86(19) . . ?
C6 N1 C5 116.5(2) . . ?
C9 N2 C8 126.3(2) . . ?
C9 N2 C28 123.5(2) . . ?
C8 N2 C28 109.96(19) . . ?
C19 N3 N1 121.2(2) . . ?
C19 N3 H39 121(2) . . ?
N1 N3 H39 114(2) . . ?
C2 C1 C20 119.5(3) . . ?
C2 C1 H1 120.3 . . ?
C20 C1 H1 120.3 . . ?
C1 C2 C3 120.5(3) . . ?
C1 C2 H19 119.7 . . ?
C3 C2 H19 119.7 . . ?
C2 C3 C4 120.5(3) . . ?
C2 C3 H18 119.7 . . ?
C4 C3 H18 119.7 . . ?
C3 C4 C21 118.8(3) . . ?
C3 C4 C5 119.4(3) . . ?
C21 C4 C5 121.7(3) . . ?
N1 C5 C4 112.7(2) . . ?
N1 C5 H17 109.1 . . ?
C4 C5 H17 109.1 . . ?
N1 C5 H22 109.1 . . ?
C4 C5 H22 109.1 . . ?
H17 C5 H22 107.8 . . ?
N1 C6 C22 110.47(19) . . ?
N1 C6 C7 114.6(2) . . ?
C22 C6 C7 111.59(19) . . ?
N1 C6 H23 106.5 . . ?
C22 C6 H23 106.5 . . ?
C7 C6 H23 106.5 . . ?
C27 C7 C8 102.78(18) . . ?
C27 C7 C14 112.7(2) . . ?
C8 C7 C14 108.0(2) . . ?
C27 C7 C6 117.7(2) . . ?
C8 C7 C6 108.0(2) . . ?
C14 C7 C6 107.25(18) . . ?
O3 C8 N2 127.6(2) . . ?
O3 C8 C7 124.5(2) . . ?
N2 C8 C7 107.9(2) . . ?
O2 C9 O1 127.6(2) . . ?
O2 C9 N2 122.5(2) . . ?
O1 C9 N2 109.9(2) . . ?
O1 C10 C13 109.4(3) . . ?
O1 C10 C11 101.4(2) . . ?
C13 C10 C11 112.5(3) . . ?
O1 C10 C12 109.5(2) . . ?
C13 C10 C12 112.1(3) . . ?
C11 C10 C12 111.5(3) . . ?
C10 C11 H37 109.5 . . ?
C10 C11 H38 109.5 . . ?
H37 C11 H38 109.5 . . ?
C10 C11 H2 109.5 . . ?
H37 C11 H2 109.5 . . ?
H38 C11 H2 109.5 . . ?
C10 C12 H3 109.5 . . ?
C10 C12 H4 109.5 . . ?
H3 C12 H4 109.5 . . ?
C10 C12 H5 109.5 . . ?
H3 C12 H5 109.5 . . ?
H4 C12 H5 109.5 . . ?
C10 C13 H8 109.5 . . ?
C10 C13 H6 109.5 . . ?
H8 C13 H6 109.5 . . ?
C10 C13 H7 109.5 . . ?
H8 C13 H7 109.5 . . ?
H6 C13 H7 109.5 . . ?
C15 C14 C19 109.6(2) . . ?
C15 C14 C7 115.78(19) . . ?
C19 C14 C7 107.7(2) . . ?
C15 C14 H9 107.8 . . ?
C19 C14 H9 107.8 . . ?
C7 C14 H9 107.8 . . ?
C16 C15 C14 108.58(19) . . ?
C16 C15 H10 110.0 . . ?
C14 C15 H10 110.0 . . ?
C16 C15 H16 110.0 . . ?
C14 C15 H16 110.0 . . ?
H10 C15 H16 108.4 . . ?
O4 C16 O5 124.2(2) . . ?
O4 C16 C15 121.7(2) . . ?
O5 C16 C15 114.1(2) . . ?
O5 C17 C18 106.9(2) . . ?
O5 C17 H15 110.3 . . ?
C18 C17 H15 110.3 . . ?
O5 C17 H11 110.3 . . ?
C18 C17 H11 110.3 . . ?
H15 C17 H11 108.6 . . ?
C17 C18 H12 109.5 . . ?
C17 C18 H14 109.5 . . ?
H12 C18 H14 109.5 . . ?
C17 C18 H13 109.5 . . ?
H12 C18 H13 109.5 . . ?
H14 C18 H13 109.5 . . ?
O6 C19 N3 124.1(2) . . ?
O6 C19 C14 122.5(2) . . ?
N3 C19 C14 113.2(2) . . ?
C21 C20 C1 120.5(3) . . ?
C21 C20 H20 119.7 . . ?
C1 C20 H20 119.7 . . ?
C20 C21 C4 120.1(3) . . ?
C20 C21 H21 119.9 . . ?
C4 C21 H21 119.9 . . ?
O8 C22 O7 126.4(2) . . ?
O8 C22 C6 125.7(2) . . ?
O7 C22 C6 107.9(2) . . ?
O7 C23 C24 109.1(2) . . ?
O7 C23 C25 110.0(2) . . ?
C24 C23 C25 113.3(3) . . ?
O7 C23 C26 101.8(2) . . ?
C24 C23 C26 111.3(3) . . ?
C25 C23 C26 110.6(3) . . ?
C23 C24 H25 109.5 . . ?
C23 C24 H24 109.5 . . ?
H25 C24 H24 109.5 . . ?
C23 C24 H26 109.5 . . ?
H25 C24 H26 109.5 . . ?
H24 C24 H26 109.5 . . ?
C23 C25 H29 109.5 . . ?
C23 C25 H28 109.5 . . ?
H29 C25 H28 109.5 . . ?
C23 C25 H27 109.5 . . ?
H29 C25 H27 109.5 . . ?
H28 C25 H27 109.5 . . ?
C23 C26 H31 109.5 . . ?
C23 C26 H30 109.5 . . ?
H31 C26 H30 109.5 . . ?
C23 C26 H32 109.5 . . ?
H31 C26 H32 109.5 . . ?
H30 C26 H32 109.5 . . ?
C32 C27 C28 119.4(2) . . ?
C32 C27 C7 130.9(2) . . ?
C28 C27 C7 109.7(2) . . ?
C29 C28 C27 121.9(2) . . ?
C29 C28 N2 128.6(2) . . ?
C27 C28 N2 109.5(2) . . ?
C28 C29 C30 117.6(2) . . ?
C28 C29 H33 121.2 . . ?
C30 C29 H33 121.2 . . ?
C31 C30 C29 121.3(3) . . ?
C31 C30 H34 119.4 . . ?
C29 C30 H34 119.4 . . ?
C30 C31 C32 120.5(3) . . ?
C30 C31 H35 119.8 . . ?
C32 C31 H35 119.8 . . ?
C31 C32 C27 119.4(2) . . ?
C31 C32 H36 120.3 . . ?
C27 C32 H36 120.3 . . ?

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
C6 N1 N3 C19 -55.5(3) . . . . ?
C5 N1 N3 C19 76.1(3) . . . . ?
C20 C1 C2 C3 -0.2(4) . . . . ?
C1 C2 C3 C4 0.4(4) . . . . ?
C2 C3 C4 C21 -0.4(4) . . . . ?
C2 C3 C4 C5 177.4(2) . . . . ?
N3 N1 C5 C4 170.0(2) . . . . ?
C6 N1 C5 C4 -61.1(3) . . . . ?
C3 C4 C5 N1 146.8(2) . . . . ?
C21 C4 C5 N1 -35.5(3) . . . . ?
N3 N1 C6 C22 -98.1(2) . . . . ?
C5 N1 C6 C22 133.3(2) . . . . ?
N3 N1 C6 C7 29.0(3) . . . . ?
C5 N1 C6 C7 -99.6(3) . . . . ?
N1 C6 C7 C27 -102.9(2) . . . . ?
C22 C6 C7 C27 23.6(3) . . . . ?
N1 C6 C7 C8 141.5(2) . . . . ?
C22 C6 C7 C8 -92.0(2) . . . . ?
N1 C6 C7 C14 25.3(3) . . . . ?
C22 C6 C7 C14 151.83(19) . . . . ?
C9 N2 C8 O3 3.9(5) . . . . ?
C28 N2 C8 O3 178.8(3) . . . . ?
C9 N2 C8 C7 -177.0(2) . . . . ?
C28 N2 C8 C7 -2.2(3) . . . . ?
C27 C7 C8 O3 -177.5(3) . . . . ?
C14 C7 C8 O3 63.2(3) . . . . ?
C6 C7 C8 O3 -52.5(3) . . . . ?
C27 C7 C8 N2 3.3(3) . . . . ?
C14 C7 C8 N2 -115.9(2) . . . . ?
C6 C7 C8 N2 128.4(2) . . . . ?
C10 O1 C9 O2 1.2(5) . . . . ?
C10 O1 C9 N2 -178.4(3) . . . . ?
C8 N2 C9 O2 174.3(3) . . . . ?
C28 N2 C9 O2 0.1(5) . . . . ?
C8 N2 C9 O1 -6.1(4) . . . . ?
C28 N2 C9 O1 179.7(2) . . . . ?
C9 O1 C10 C13 59.7(4) . . . . ?
C9 O1 C10 C11 178.7(3) . . . . ?
C9 O1 C10 C12 -63.5(4) . . . . ?
C27 C7 C14 C15 -52.8(3) . . . . ?
C8 C7 C14 C15 60.0(3) . . . . ?
C6 C7 C14 C15 176.1(2) . . . . ?
C27 C7 C14 C19 70.2(2) . . . . ?
C8 C7 C14 C19 -177.0(2) . . . . ?
C6 C7 C14 C19 -60.8(2) . . . . ?
C19 C14 C15 C16 65.0(3) . . . . ?
C7 C14 C15 C16 -172.89(19) . . . . ?
C17 O5 C16 O4 -4.1(3) . . . . ?
C17 O5 C16 C15 177.05(19) . . . . ?
C14 C15 C16 O4 40.6(3) . . . . ?
C14 C15 C16 O5 -140.5(2) . . . . ?
C16 O5 C17 C18 174.7(2) . . . . ?
N1 N3 C19 O6 -168.0(2) . . . . ?
N1 N3 C19 C14 16.8(3) . . . . ?
C15 C14 C19 O6 -6.2(3) . . . . ?
C7 C14 C19 O6 -132.9(3) . . . . ?
C15 C14 C19 N3 169.2(2) . . . . ?
C7 C14 C19 N3 42.4(3) . . . . ?
C2 C1 C20 C21 0.0(4) . . . . ?
C1 C20 C21 C4 0.0(4) . . . . ?
C3 C4 C21 C20 0.2(4) . . . . ?
C5 C4 C21 C20 -177.5(2) . . . . ?
C23 O7 C22 O8 4.1(4) . . . . ?
C23 O7 C22 C6 -177.5(2) . . . . ?
N1 C6 C22 O8 3.4(4) . . . . ?
C7 C6 C22 O8 -125.4(3) . . . . ?
N1 C6 C22 O7 -174.9(2) . . . . ?
C7 C6 C22 O7 56.3(3) . . . . ?
C22 O7 C23 C24 -66.0(3) . . . . ?
C22 O7 C23 C25 58.9(3) . . . . ?
C22 O7 C23 C26 176.2(3) . . . . ?
C8 C7 C27 C32 178.9(3) . . . . ?
C14 C7 C27 C32 -65.1(4) . . . . ?
C6 C7 C27 C32 60.5(4) . . . . ?
C8 C7 C27 C28 -3.4(3) . . . . ?
C14 C7 C27 C28 112.5(2) . . . . ?
C6 C7 C27 C28 -121.9(2) . . . . ?
C32 C27 C28 C29 0.4(4) . . . . ?
C7 C27 C28 C29 -177.5(3) . . . . ?
C32 C27 C28 N2 -179.7(2) . . . . ?
C7 C27 C28 N2 2.3(3) . . . . ?
C9 N2 C28 C29 -5.2(5) . . . . ?
C8 N2 C28 C29 179.8(3) . . . . ?
C9 N2 C28 C27 175.0(2) . . . . ?
C8 N2 C28 C27 -0.1(3) . . . . ?
C27 C28 C29 C30 0.2(5) . . . . ?
N2 C28 C29 C30 -179.7(3) . . . . ?
C28 C29 C30 C31 -0.8(5) . . . . ?
C29 C30 C31 C32 0.9(5) . . . . ?
C30 C31 C32 C27 -0.2(5) . . . . ?
C28 C27 C32 C31 -0.4(4) . . . . ?
C7 C27 C32 C31 177.0(3) . . . . ?

_refine_diff_density_max         0.159
_refine_diff_density_min         -0.150
_refine_diff_density_rms         0.037

####################################################################### 
# 
# 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_20190417tangQG_0ma
_database_code_depnum_ccdc_archive 'CCDC 2153695'
loop_
_audit_author_name
_audit_author_address
Tianhengzhi
;Fudan University
China
;
_audit_update_record             
;
2022-02-21 deposited with the CCDC.	2022-05-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H26 N2 O6'
_chemical_formula_weight         390.43

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   11.2293(6)
_cell_length_b                   8.1032(5)
_cell_length_c                   11.2293(6)
_cell_angle_alpha                90
_cell_angle_beta                 100.54
_cell_angle_gamma                90
_cell_volume                     1004.56(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    274(2)
_cell_measurement_reflns_used    9144
_cell_measurement_theta_min      4.00
_cell_measurement_theta_max      72.63

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.291
_exptl_crystal_F_000             416
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.070
_exptl_absorpt_coefficient_mu    0.793
_shelx_estimated_absorpt_T_min   0.797
_shelx_estimated_absorpt_T_max   0.947
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      274(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9600
_diffrn_reflns_av_unetI/netI     0.0611
_diffrn_reflns_av_R_equivalents  0.0591
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         4.004
_diffrn_reflns_theta_max         72.847
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.765
_diffrn_reflns_point_group_measured_fraction_full 0.784
_reflns_number_total             3056
_reflns_number_gt                2984
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.448
_reflns_Friedel_fraction_max     0.511
_reflns_Friedel_fraction_full    0.541

_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.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0651P)²+0.0605P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 879 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.02(14)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         3056
_refine_ls_number_parameters     265
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0439
_refine_ls_R_factor_gt           0.0434
_refine_ls_wR_factor_ref         0.1016
_refine_ls_wR_factor_gt          0.1008
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_restrained_S_all      1.091
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 0.70089(13) 0.36801(19) 0.48857(13) 0.0241(3) Uani 1 1 d . . . . .
O2 O 0.20740(13) 0.7716(2) 0.04132(14) 0.0271(3) Uani 1 1 d . . . . .
O3 O 0.47827(16) 0.1706(2) 0.12388(15) 0.0320(4) Uani 1 1 d . . . . .
O4 O 0.42628(14) 0.48128(19) 0.45003(13) 0.0252(3) Uani 1 1 d . . . . .
O5 O 0.17184(15) 0.5026(2) 0.06500(18) 0.0388(4) Uani 1 1 d . . . . .
O6 O 0.79438(14) 0.2052(2) 0.36949(14) 0.0283(3) Uani 1 1 d . . . . .
N1 N 0.59933(17) 0.2000(2) 0.19239(16) 0.0262(4) Uani 1 1 d . . . . .
H18 H 0.623(3) 0.094(4) 0.211(2) 0.026(6) Uiso 1 1 d . . . . .
N2 N 0.55490(17) 0.6848(2) 0.40614(16) 0.0231(4) Uani 1 1 d . . . . .
H27 H 0.546(3) 0.754(5) 0.459(3) 0.034(7) Uiso 1 1 d . . . . .
C1 C 0.7592(3) 0.5054(4) 0.6725(2) 0.0454(7) Uani 1 1 d . . . . .
H1 H 0.734451 0.608875 0.634241 0.068 Uiso 1 1 calc R U . . .
H21 H 0.820384 0.524433 0.742901 0.068 Uiso 1 1 calc R U . . .
H22 H 0.690674 0.452439 0.696194 0.068 Uiso 1 1 calc R U . . .
C2 C 0.8099(2) 0.3954(3) 0.5844(2) 0.0307(5) Uani 1 1 d . . . . .
C3 C 0.70682(18) 0.2785(2) 0.39063(18) 0.0211(4) Uani 1 1 d . . . . .
C4 C 0.58339(18) 0.2776(2) 0.30627(17) 0.0199(4) Uani 1 1 d . . . . .
H20 H 0.525470 0.213712 0.343062 0.024 Uiso 1 1 calc R U . . .
C5 C 0.53440(17) 0.4541(2) 0.27794(16) 0.0187(4) Uani 1 1 d . . . . .
C6 C 0.41663(19) 0.4426(3) 0.17952(18) 0.0220(4) Uani 1 1 d . . . . .
H15 H 0.352665 0.395571 0.217934 0.026 Uiso 1 1 calc R U . . .
C7 C 0.37387(18) 0.6123(3) 0.12943(18) 0.0225(4) Uani 1 1 d . . . . .
H10 H 0.390618 0.692717 0.194310 0.027 Uiso 1 1 calc R U . . .
H9 H 0.420088 0.643468 0.067944 0.027 Uiso 1 1 calc R U . . .
C8 C 0.24041(19) 0.6185(3) 0.07497(18) 0.0238(4) Uani 1 1 d . . . . .
C9 C 0.0792(2) 0.8001(3) -0.0065(2) 0.0317(5) Uani 1 1 d . . . . .
H11 H 0.061056 0.916081 0.002121 0.038 Uiso 1 1 calc R U . . .
H12 H 0.030962 0.737191 0.040871 0.038 Uiso 1 1 calc R U . . .
C10 C 0.0444(2) 0.7520(4) -0.1370(2) 0.0373(6) Uani 1 1 d . . . . .
H2 H 0.098005 0.804402 -0.182873 0.056 Uiso 1 1 calc R U . . .
H13 H -0.037311 0.786353 -0.167344 0.056 Uiso 1 1 calc R U . . .
H14 H 0.050263 0.634369 -0.144361 0.056 Uiso 1 1 calc R U . . .
C11 C 0.8524(2) 0.2306(3) 0.6419(2) 0.0358(6) Uani 1 1 d . . . . .
H4 H 0.784503 0.172076 0.662202 0.054 Uiso 1 1 calc R U . . .
H3 H 0.911415 0.249291 0.713991 0.054 Uiso 1 1 calc R U . . .
H26 H 0.888058 0.166344 0.585705 0.054 Uiso 1 1 calc R U . . .
C12 C 0.4352(2) 0.3276(3) 0.0779(2) 0.0304(5) Uani 1 1 d . . . . .
H17 H 0.359181 0.313844 0.021876 0.036 Uiso 1 1 calc R U . . .
H16 H 0.493199 0.376164 0.033816 0.036 Uiso 1 1 calc R U . . .
C13 C 0.49825(18) 0.5378(3) 0.38969(17) 0.0196(4) Uani 1 1 d . . . . .
C14 C 0.63819(18) 0.7047(2) 0.32773(18) 0.0214(4) Uani 1 1 d . . . . .
C15 C 0.7214(2) 0.8309(3) 0.3288(2) 0.0285(5) Uani 1 1 d . . . . .
H8 H 0.726437 0.917860 0.383588 0.034 Uiso 1 1 calc R U . . .
C16 C 0.7973(2) 0.8212(3) 0.2439(2) 0.0323(5) Uani 1 1 d . . . . .
H7 H 0.853115 0.905107 0.240566 0.039 Uiso 1 1 calc R U . . .
C17 C 0.7916(2) 0.6900(3) 0.1645(2) 0.0315(5) Uani 1 1 d . . . . .
H5 H 0.844147 0.686318 0.109460 0.038 Uiso 1 1 calc R U . . .
C18 C 0.70780(19) 0.5625(3) 0.16595(18) 0.0246(4) Uani 1 1 d . . . . .
H6 H 0.704377 0.473934 0.112761 0.030 Uiso 1 1 calc R U . . .
C19 C 0.62992(17) 0.5712(2) 0.24848(16) 0.0190(4) Uani 1 1 d . . . . .
C20 C 0.9068(2) 0.4834(4) 0.5298(3) 0.0428(6) Uani 1 1 d . . . . .
H24 H 0.938747 0.409297 0.476708 0.064 Uiso 1 1 calc R U . . .
H23 H 0.970929 0.518585 0.593359 0.064 Uiso 1 1 calc R U . . .
H25 H 0.871978 0.577731 0.484689 0.064 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C3 1.329(3) . ?
O1 C2 1.492(2) . ?
O2 C8 1.330(3) . ?
O2 C9 1.460(2) . ?
O3 C12 1.424(3) . ?
O3 N1 1.454(2) . ?
O4 C13 1.234(3) . ?
O5 C8 1.207(3) . ?
O6 C3 1.209(3) . ?
N1 C4 1.465(2) . ?
N1 H18 0.91(3) . ?
N2 C13 1.347(3) . ?
N2 C14 1.406(3) . ?
N2 H27 0.83(4) . ?
C1 C2 1.518(4) . ?
C1 H1 0.9600 . ?
C1 H21 0.9600 . ?
C1 H22 0.9600 . ?
C2 C20 1.521(4) . ?
C2 C11 1.522(3) . ?
C3 C4 1.529(3) . ?
C4 C5 1.544(3) . ?
C4 H20 0.9800 . ?
C5 C19 1.513(3) . ?
C5 C13 1.544(3) . ?
C5 C6 1.564(3) . ?
C6 C12 1.517(3) . ?
C6 C7 1.529(3) . ?
C6 H15 0.9800 . ?
C7 C8 1.512(3) . ?
C7 H10 0.9700 . ?
C7 H9 0.9700 . ?
C9 C10 1.498(3) . ?
C9 H11 0.9700 . ?
C9 H12 0.9700 . ?
C10 H2 0.9600 . ?
C10 H13 0.9600 . ?
C10 H14 0.9600 . ?
C11 H4 0.9600 . ?
C11 H3 0.9600 . ?
C11 H26 0.9600 . ?
C12 H17 0.9700 . ?
C12 H16 0.9700 . ?
C14 C15 1.384(3) . ?
C14 C19 1.393(3) . ?
C15 C16 1.392(4) . ?
C15 H8 0.9300 . ?
C16 C17 1.382(4) . ?
C16 H7 0.9300 . ?
C17 C18 1.399(3) . ?
C17 H5 0.9300 . ?
C18 C19 1.387(3) . ?
C18 H6 0.9300 . ?
C20 H24 0.9600 . ?
C20 H23 0.9600 . ?
C20 H25 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 O1 C2 121.30(17) . . ?
C8 O2 C9 117.18(18) . . ?
C12 O3 N1 105.55(16) . . ?
O3 N1 C4 106.29(16) . . ?
O3 N1 H18 99.6(18) . . ?
C4 N1 H18 106.6(18) . . ?
C13 N2 C14 111.56(17) . . ?
C13 N2 H27 125(2) . . ?
C14 N2 H27 123(2) . . ?
C2 C1 H1 109.5 . . ?
C2 C1 H21 109.5 . . ?
H1 C1 H21 109.5 . . ?
C2 C1 H22 109.5 . . ?
H1 C1 H22 109.5 . . ?
H21 C1 H22 109.5 . . ?
O1 C2 C1 101.61(19) . . ?
O1 C2 C20 109.38(18) . . ?
C1 C2 C20 111.7(3) . . ?
O1 C2 C11 109.12(19) . . ?
C1 C2 C11 111.4(2) . . ?
C20 C2 C11 113.0(2) . . ?
O6 C3 O1 126.59(19) . . ?
O6 C3 C4 123.63(18) . . ?
O1 C3 C4 109.77(16) . . ?
N1 C4 C3 107.53(16) . . ?
N1 C4 C5 108.28(15) . . ?
C3 C4 C5 111.83(15) . . ?
N1 C4 H20 109.7 . . ?
C3 C4 H20 109.7 . . ?
C5 C4 H20 109.7 . . ?
C19 C5 C13 101.80(15) . . ?
C19 C5 C4 112.68(16) . . ?
C13 C5 C4 112.07(15) . . ?
C19 C5 C6 115.13(15) . . ?
C13 C5 C6 106.66(16) . . ?
C4 C5 C6 108.28(15) . . ?
C12 C6 C7 110.64(17) . . ?
C12 C6 C5 110.70(17) . . ?
C7 C6 C5 111.98(16) . . ?
C12 C6 H15 107.8 . . ?
C7 C6 H15 107.8 . . ?
C5 C6 H15 107.8 . . ?
C8 C7 C6 113.56(17) . . ?
C8 C7 H10 108.9 . . ?
C6 C7 H10 108.9 . . ?
C8 C7 H9 108.9 . . ?
C6 C7 H9 108.9 . . ?
H10 C7 H9 107.7 . . ?
O5 C8 O2 124.05(19) . . ?
O5 C8 C7 125.5(2) . . ?
O2 C8 C7 110.48(17) . . ?
O2 C9 C10 112.43(19) . . ?
O2 C9 H11 109.1 . . ?
C10 C9 H11 109.1 . . ?
O2 C9 H12 109.1 . . ?
C10 C9 H12 109.1 . . ?
H11 C9 H12 107.8 . . ?
C9 C10 H2 109.5 . . ?
C9 C10 H13 109.5 . . ?
H2 C10 H13 109.5 . . ?
C9 C10 H14 109.5 . . ?
H2 C10 H14 109.5 . . ?
H13 C10 H14 109.5 . . ?
C2 C11 H4 109.5 . . ?
C2 C11 H3 109.5 . . ?
H4 C11 H3 109.5 . . ?
C2 C11 H26 109.5 . . ?
H4 C11 H26 109.5 . . ?
H3 C11 H26 109.5 . . ?
O3 C12 C6 111.10(18) . . ?
O3 C12 H17 109.4 . . ?
C6 C12 H17 109.4 . . ?
O3 C12 H16 109.4 . . ?
C6 C12 H16 109.4 . . ?
H17 C12 H16 108.0 . . ?
O4 C13 N2 126.38(19) . . ?
O4 C13 C5 125.40(19) . . ?
N2 C13 C5 108.17(17) . . ?
C15 C14 C19 123.1(2) . . ?
C15 C14 N2 127.2(2) . . ?
C19 C14 N2 109.65(17) . . ?
C14 C15 C16 116.7(2) . . ?
C14 C15 H8 121.7 . . ?
C16 C15 H8 121.7 . . ?
C17 C16 C15 121.6(2) . . ?
C17 C16 H7 119.2 . . ?
C15 C16 H7 119.2 . . ?
C16 C17 C18 120.8(2) . . ?
C16 C17 H5 119.6 . . ?
C18 C17 H5 119.6 . . ?
C19 C18 C17 118.5(2) . . ?
C19 C18 H6 120.7 . . ?
C17 C18 H6 120.7 . . ?
C18 C19 C14 119.32(19) . . ?
C18 C19 C5 132.27(19) . . ?
C14 C19 C5 108.33(17) . . ?
C2 C20 H24 109.5 . . ?
C2 C20 H23 109.5 . . ?
H24 C20 H23 109.5 . . ?
C2 C20 H25 109.5 . . ?
H24 C20 H25 109.5 . . ?
H23 C20 H25 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C12 O3 N1 C4 75.6(2) . . . . ?
C3 O1 C2 C1 178.5(2) . . . . ?
C3 O1 C2 C20 60.4(3) . . . . ?
C3 O1 C2 C11 -63.7(3) . . . . ?
C2 O1 C3 O6 3.4(3) . . . . ?
C2 O1 C3 C4 -177.65(17) . . . . ?
O3 N1 C4 C3 168.81(15) . . . . ?
O3 N1 C4 C5 -70.20(19) . . . . ?
O6 C3 C4 N1 -9.7(3) . . . . ?
O1 C3 C4 N1 171.34(16) . . . . ?
O6 C3 C4 C5 -128.4(2) . . . . ?
O1 C3 C4 C5 52.6(2) . . . . ?
N1 C4 C5 C19 -73.62(19) . . . . ?
C3 C4 C5 C19 44.7(2) . . . . ?
N1 C4 C5 C13 172.26(17) . . . . ?
C3 C4 C5 C13 -69.4(2) . . . . ?
N1 C4 C5 C6 54.9(2) . . . . ?
C3 C4 C5 C6 173.19(16) . . . . ?
C19 C5 C6 C12 81.2(2) . . . . ?
C13 C5 C6 C12 -166.75(19) . . . . ?
C4 C5 C6 C12 -46.0(2) . . . . ?
C19 C5 C6 C7 -42.8(2) . . . . ?
C13 C5 C6 C7 69.3(2) . . . . ?
C4 C5 C6 C7 -169.95(16) . . . . ?
C12 C6 C7 C8 79.1(2) . . . . ?
C5 C6 C7 C8 -156.88(17) . . . . ?
C9 O2 C8 O5 2.2(3) . . . . ?
C9 O2 C8 C7 -176.41(17) . . . . ?
C6 C7 C8 O5 -3.2(3) . . . . ?
C6 C7 C8 O2 175.44(17) . . . . ?
C8 O2 C9 C10 -80.9(3) . . . . ?
N1 O3 C12 C6 -67.0(2) . . . . ?
C7 C6 C12 O3 178.39(17) . . . . ?
C5 C6 C12 O3 53.6(2) . . . . ?
C14 N2 C13 O4 175.21(19) . . . . ?
C14 N2 C13 C5 -7.3(2) . . . . ?
C19 C5 C13 O4 -175.96(18) . . . . ?
C4 C5 C13 O4 -55.3(2) . . . . ?
C6 C5 C13 O4 63.0(2) . . . . ?
C19 C5 C13 N2 6.5(2) . . . . ?
C4 C5 C13 N2 127.16(17) . . . . ?
C6 C5 C13 N2 -114.51(17) . . . . ?
C13 N2 C14 C15 -172.1(2) . . . . ?
C13 N2 C14 C19 5.0(2) . . . . ?
C19 C14 C15 C16 1.3(3) . . . . ?
N2 C14 C15 C16 178.05(19) . . . . ?
C14 C15 C16 C17 -1.5(3) . . . . ?
C15 C16 C17 C18 0.8(3) . . . . ?
C16 C17 C18 C19 0.4(3) . . . . ?
C17 C18 C19 C14 -0.6(3) . . . . ?
C17 C18 C19 C5 -176.8(2) . . . . ?
C15 C14 C19 C18 -0.2(3) . . . . ?
N2 C14 C19 C18 -177.48(17) . . . . ?
C15 C14 C19 C5 176.85(18) . . . . ?
N2 C14 C19 C5 -0.4(2) . . . . ?
C13 C5 C19 C18 173.0(2) . . . . ?
C4 C5 C19 C18 52.8(3) . . . . ?
C6 C5 C19 C18 -72.1(3) . . . . ?
C13 C5 C19 C14 -3.54(19) . . . . ?
C4 C5 C19 C14 -123.76(17) . . . . ?
C6 C5 C19 C14 111.39(18) . . . . ?

_refine_diff_density_max         0.334
_refine_diff_density_min         -0.256
_refine_diff_density_rms         0.058

