# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_lslt99
_database_code_depnum_ccdc_archive 'CCDC 2070473'
loop_
_audit_author_name
_audit_author_address
'Tao Feng'
;South Central University for Nationalities
China
;
_audit_update_record             
;
2021-03-15 deposited with the CCDC.	2021-05-19 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C25 H35 N O5'
_chemical_formula_iupac          ?
_chemical_formula_weight         429.54
_chemical_absolute_configuration ad

_chemical_melting_point          ?

_space_group_crystal_system      hexagonal
_space_group_name_H-M_alt        'P 65'
_space_group_name_Hall           'P 65'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x-y, x, z+5/6'
'y, -x+y, z+1/6'
'-y, x-y, z+2/3'
'-x+y, -x, z+1/3'
'-x, -y, z+1/2'

_cell_length_a                   17.6760(4)
_cell_length_b                   17.6760(4)
_cell_length_c                   13.1360(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     3554.36(19)
_cell_formula_units_Z            6
_cell_measurement_reflns_used    9847
_cell_measurement_theta_min      4.4353
_cell_measurement_theta_max      78.9492
_cell_measurement_temperature    156.(2)

_exptl_crystal_description       NEEDLE
_exptl_crystal_colour            'light colourless'
_exptl_crystal_size_max          0.153
_exptl_crystal_size_mid          0.096
_exptl_crystal_size_min          0.095
_exptl_crystal_density_diffrn    1.204
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1392

_exptl_absorpt_coefficient_mu    0.669
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_correction_T_min  0.86
_exptl_absorpt_correction_T_max  0.94

_exptl_special_details           
;
;

_diffrn_ambient_temperature      156.(2)

_diffrn_source                   ?
_diffrn_source_type              ?

_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_monochromator  ?

_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'


_diffrn_detector_area_resol_mean 7.3910

_diffrn_reflns_number            83650
_diffrn_reflns_av_R_equivalents  0.0490
_diffrn_reflns_av_unetI/netI     0.0164
_diffrn_reflns_theta_min         2.89
_diffrn_reflns_theta_max         79.21
_diffrn_reflns_theta_full        79.21
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       16

_refine_special_details          
;
;

_reflns_number_total             5041
_reflns_number_gt                4897
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0299
_refine_ls_R_factor_gt           0.0285
_refine_ls_wR_factor_gt          0.0676
_refine_ls_wR_factor_ref         0.0688
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_restrained_S_all      1.077
_refine_ls_number_reflns         5041
_refine_ls_number_parameters     293
_refine_ls_number_restraints     1
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0332P)²+0.4945P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.126
_refine_diff_density_min         -0.153
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
;

Flack x determined using 2229 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.03(5)

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'

_computing_data_collection       ?
_computing_cell_refinement       'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 833)'
_computing_publication_material  ?

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.67143(10) 0.50436(10) 0.51326(13) 0.0230(3) Uani d . . . 1 . .
H H1 0.7484(13) 0.3794(13) 0.5630(17) 0.025(5) Uiso d . . . 1 . .
O O2 0.53739(8) 0.40427(8) 0.42595(10) 0.0287(2) Uani d . . . 1 . .
H H2 0.5136(9) 0.3629(17) 0.384(2) 0.043 Uiso calc U . R 1 . .
C C2 0.73508(10) 0.48222(10) 0.56716(12) 0.0231(3) Uani d . . . 1 . .
O O3 0.67282(8) 0.46285(7) 0.34544(9) 0.0283(2) Uani d . . . 1 . .
C C3 0.64301(10) 0.35492(10) 0.47137(13) 0.0251(3) Uani d . . . 1 . .
H H3 0.659949 0.332825 0.41043 0.03 Uiso calc U . R 1 . .
C C4 0.62472(10) 0.42848(10) 0.43708(13) 0.0242(3) Uani d . . . 1 . .
O O4 0.55776(8) 0.45868(8) 0.64155(10) 0.0320(3) Uani d . . . 1 . .
O O5 0.55061(9) 0.29931(9) 0.62502(10) 0.0350(3) Uani d . . . 1 . .
H H5A 0.5429(18) 0.3416(19) 0.6190(4) 0.053 Uiso calc U . R 1 . .
C C5 0.71050(10) 0.55723(10) 0.33798(13) 0.0255(3) Uani d . . . 1 . .
H H5 0.771586 0.582028 0.312127 0.031 Uiso calc U . R 1 . .
N N1 0.71970(9) 0.40390(9) 0.53535(11) 0.0248(3) Uani d . . . 1 . .
O O1 0.79167(7) 0.53015(7) 0.62818(9) 0.0263(2) Uani d . . . 1 . .
C C6 0.71633(10) 0.58932(10) 0.44966(13) 0.0243(3) Uani d . . . 1 . .
H H6 0.779196 0.623923 0.469904 0.029 Uiso calc U . R 1 . .
C C7 0.66971(11) 0.64196(11) 0.47919(13) 0.0272(3) Uani d . . . 1 . .
H H7 0.619836 0.624783 0.431144 0.033 Uiso calc U . R 1 . .
C C11 0.82126(12) 0.80251(11) 0.73167(15) 0.0332(4) Uani d . . . 1 . .
H H11A 0.868511 0.795712 0.700473 0.04 Uiso calc U . R 1 . .
H H11B 0.840963 0.865681 0.733755 0.04 Uiso calc U . R 1 . .
C C10 0.73916(11) 0.75585(11) 0.66491(14) 0.0300(4) Uani d . . . 1 . .
H H10 0.693079 0.76627 0.694656 0.036 Uiso calc U . R 1 . .
C C9 0.75648(13) 0.78971(11) 0.55740(15) 0.0341(4) Uani d . . . 1 . .
H H9 0.790498 0.851164 0.548335 0.041 Uiso calc U . R 1 . .
C C8 0.72801(12) 0.74054(11) 0.47386(15) 0.0325(4) Uani d . . . 1 . .
C C12 0.80569(12) 0.76699(12) 0.84050(15) 0.0343(4) Uani d . . . 1 . .
H H12 0.762303 0.779963 0.873095 0.041 Uiso calc U . R 1 . .
C C17 0.61180(10) 0.51599(11) 0.58807(13) 0.0257(3) Uani d . . . 1 . .
C C16 0.63150(11) 0.60945(11) 0.58670(14) 0.0271(3) Uani d . . . 1 . .
C C15 0.70567(11) 0.65768(10) 0.66625(13) 0.0266(3) Uani d . . . 1 . .
H H15 0.755425 0.649881 0.643866 0.032 Uiso calc U . R 1 . .
C C14 0.68374(12) 0.62313(12) 0.77548(15) 0.0328(4) Uani d . . . 1 . .
H H14A 0.639083 0.635247 0.804159 0.039 Uiso calc U . R 1 . .
H H14B 0.659882 0.559143 0.776009 0.039 Uiso calc U . R 1 . .
C C13 0.76664(13) 0.66802(12) 0.83951(15) 0.0350(4) Uani d . . . 1 . .
H H13A 0.810111 0.65379 0.811727 0.042 Uiso calc U . R 1 . .
H H13B 0.753011 0.645613 0.910133 0.042 Uiso calc U . R 1 . .
C C19 0.59319(12) 0.20646(11) 0.54738(16) 0.0348(4) Uani d . . . 1 . .
H H19A 0.606178 0.188087 0.482441 0.052 Uiso calc U . R 1 . .
H H19B 0.544181 0.15615 0.580527 0.052 Uiso calc U . R 1 . .
H H19C 0.644707 0.229878 0.591562 0.052 Uiso calc U . R 1 . .
C C18 0.56912(11) 0.27675(11) 0.52815(14) 0.0290(3) Uani d . . . 1 . .
H H18 0.514997 0.251455 0.485597 0.035 Uiso calc U . R 1 . .
C C20 0.66120(11) 0.57860(11) 0.26173(14) 0.0278(3) Uani d . . . 1 . .
H H20 0.602634 0.563311 0.276489 0.033 Uiso calc U . R 1 . .
C C21 0.69597(12) 0.61788(14) 0.17476(16) 0.0398(4) Uani d . . . 1 . .
H H21 0.75411 0.63114 0.161068 0.048 Uiso calc U . R 1 . .
C C22 0.65195(15) 0.64342(19) 0.0957(2) 0.0582(7) Uani d . . . 1 . .
H H22A 0.688571 0.705696 0.080067 0.087 Uiso calc U . R 1 . .
H H22B 0.595245 0.632263 0.121498 0.087 Uiso calc U . R 1 . .
H H22C 0.643188 0.609038 0.03382 0.087 Uiso calc U . R 1 . .
C C23 0.75024(16) 0.78050(13) 0.36931(17) 0.0430(5) Uani d . . . 1 . .
H H23A 0.783706 0.758692 0.332493 0.065 Uiso calc U . R 1 . .
H H23B 0.785226 0.844215 0.375268 0.065 Uiso calc U . R 1 . .
H H23C 0.696289 0.764637 0.332042 0.065 Uiso calc U . R 1 . .
C C24 0.88938(14) 0.81108(15) 0.90395(18) 0.0439(5) Uani d . . . 1 . .
H H24A 0.932813 0.798699 0.873969 0.066 Uiso calc U . R 1 . .
H H24B 0.876479 0.788471 0.973717 0.066 Uiso calc U . R 1 . .
H H24C 0.912503 0.874339 0.904851 0.066 Uiso calc U . R 1 . .
C C25 0.54996(12) 0.61592(13) 0.60855(16) 0.0346(4) Uani d . . . 1 . .
H H25A 0.563289 0.67628 0.598386 0.052 Uiso calc U . R 1 . .
H H25B 0.531362 0.598372 0.67907 0.052 Uiso calc U . R 1 . .
H H25C 0.502952 0.57724 0.562198 0.052 Uiso calc U . R 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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C17 . 1.528(2) ?
C1 C2 . 1.536(2) ?
C1 C4 . 1.541(2) ?
C1 C6 . 1.546(2) ?
O2 C4 . 1.3881(19) ?
O2 H2 . 0.84(3) ?
C2 O1 . 1.230(2) ?
C2 N1 . 1.337(2) ?
O3 C4 . 1.423(2) ?
O3 C5 . 1.4578(19) ?
C3 N1 . 1.456(2) ?
C3 C18 . 1.538(2) ?
C3 C4 . 1.555(2) ?
C3 H3 . 1.0 ?
O4 C17 . 1.210(2) ?
O5 C18 . 1.420(2) ?
O5 H5A . 0.83(3) ?
C5 C20 . 1.495(2) ?
C5 C6 . 1.558(2) ?
C5 H5 . 1.0 ?
N1 H1 . 0.89(2) ?
C6 C7 . 1.569(2) ?
C6 H6 . 1.0 ?
C7 C8 . 1.519(2) ?
C7 C16 . 1.547(2) ?
C7 H7 . 1.0 ?
C11 C12 . 1.530(3) ?
C11 C10 . 1.536(2) ?
C11 H11A . 0.99 ?
C11 H11B . 0.99 ?
C10 C9 . 1.504(3) ?
C10 C15 . 1.528(2) ?
C10 H10 . 1.0 ?
C9 C8 . 1.333(3) ?
C9 H9 . 0.95 ?
C8 C23 . 1.504(3) ?
C12 C13 . 1.526(3) ?
C12 C24 . 1.529(3) ?
C12 H12 . 1.0 ?
C17 C16 . 1.508(2) ?
C16 C25 . 1.529(2) ?
C16 C15 . 1.556(2) ?
C15 C14 . 1.531(3) ?
C15 H15 . 1.0 ?
C14 C13 . 1.524(3) ?
C14 H14A . 0.99 ?
C14 H14B . 0.99 ?
C13 H13A . 0.99 ?
C13 H13B . 0.99 ?
C19 C18 . 1.522(2) ?
C19 H19A . 0.98 ?
C19 H19B . 0.98 ?
C19 H19C . 0.98 ?
C18 H18 . 1.0 ?
C20 C21 . 1.318(3) ?
C20 H20 . 0.95 ?
C21 C22 . 1.496(3) ?
C21 H21 . 0.95 ?
C22 H22A . 0.98 ?
C22 H22B . 0.98 ?
C22 H22C . 0.98 ?
C23 H23A . 0.98 ?
C23 H23B . 0.98 ?
C23 H23C . 0.98 ?
C24 H24A . 0.98 ?
C24 H24B . 0.98 ?
C24 H24C . 0.98 ?
C25 H25A . 0.98 ?
C25 H25B . 0.98 ?
C25 H25C . 0.98 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C17 C1 C2 . . 112.34(13) ?
C17 C1 C4 . . 115.42(13) ?
C2 C1 C4 . . 102.68(12) ?
C17 C1 C6 . . 105.68(12) ?
C2 C1 C6 . . 114.25(12) ?
C4 C1 C6 . . 106.61(13) ?
C4 O2 H2 . . 109.5 ?
O1 C2 N1 . . 126.23(15) ?
O1 C2 C1 . . 124.86(14) ?
N1 C2 C1 . . 108.90(13) ?
C4 O3 C5 . . 112.28(12) ?
N1 C3 C18 . . 111.96(14) ?
N1 C3 C4 . . 101.01(12) ?
C18 C3 C4 . . 116.97(13) ?
N1 C3 H3 . . 108.8 ?
C18 C3 H3 . . 108.8 ?
C4 C3 H3 . . 108.8 ?
O2 C4 O3 . . 112.18(14) ?
O2 C4 C1 . . 111.47(13) ?
O3 C4 C1 . . 103.42(12) ?
O2 C4 C3 . . 115.90(13) ?
O3 C4 C3 . . 105.81(12) ?
C1 C4 C3 . . 107.14(13) ?
C18 O5 H5A . . 109.5 ?
O3 C5 C20 . . 110.10(13) ?
O3 C5 C6 . . 105.22(12) ?
C20 C5 C6 . . 118.67(13) ?
O3 C5 H5 . . 107.4 ?
C20 C5 H5 . . 107.4 ?
C6 C5 H5 . . 107.4 ?
C2 N1 C3 . . 116.29(13) ?
C2 N1 H1 . . 120.3(13) ?
C3 N1 H1 . . 122.2(13) ?
C1 C6 C5 . . 104.29(12) ?
C1 C6 C7 . . 106.00(13) ?
C5 C6 C7 . . 119.34(13) ?
C1 C6 H6 . . 108.9 ?
C5 C6 H6 . . 108.9 ?
C7 C6 H6 . . 108.9 ?
C8 C7 C16 . . 112.83(14) ?
C8 C7 C6 . . 114.37(14) ?
C16 C7 C6 . . 105.46(13) ?
C8 C7 H7 . . 108.0 ?
C16 C7 H7 . . 108.0 ?
C6 C7 H7 . . 108.0 ?
C12 C11 C10 . . 112.67(15) ?
C12 C11 H11A . . 109.1 ?
C10 C11 H11A . . 109.1 ?
C12 C11 H11B . . 109.1 ?
C10 C11 H11B . . 109.1 ?
H11A C11 H11B . . 107.8 ?
C9 C10 C15 . . 110.42(14) ?
C9 C10 C11 . . 111.88(15) ?
C15 C10 C11 . . 109.19(14) ?
C9 C10 H10 . . 108.4 ?
C15 C10 H10 . . 108.4 ?
C11 C10 H10 . . 108.4 ?
C8 C9 C10 . . 125.33(16) ?
C8 C9 H9 . . 117.3 ?
C10 C9 H9 . . 117.3 ?
C9 C8 C23 . . 121.40(16) ?
C9 C8 C7 . . 121.91(16) ?
C23 C8 C7 . . 116.67(16) ?
C13 C12 C24 . . 110.90(17) ?
C13 C12 C11 . . 110.35(15) ?
C24 C12 C11 . . 111.75(16) ?
C13 C12 H12 . . 107.9 ?
C24 C12 H12 . . 107.9 ?
C11 C12 H12 . . 107.9 ?
O4 C17 C16 . . 125.24(15) ?
O4 C17 C1 . . 124.72(15) ?
C16 C17 C1 . . 110.03(13) ?
C17 C16 C25 . . 111.69(14) ?
C17 C16 C7 . . 103.69(13) ?
C25 C16 C7 . . 113.35(15) ?
C17 C16 C15 . . 105.19(13) ?
C25 C16 C15 . . 113.62(14) ?
C7 C16 C15 . . 108.54(13) ?
C10 C15 C14 . . 109.92(14) ?
C10 C15 C16 . . 110.88(14) ?
C14 C15 C16 . . 115.78(14) ?
C10 C15 H15 . . 106.6 ?
C14 C15 H15 . . 106.6 ?
C16 C15 H15 . . 106.6 ?
C13 C14 C15 . . 108.89(15) ?
C13 C14 H14A . . 109.9 ?
C15 C14 H14A . . 109.9 ?
C13 C14 H14B . . 109.9 ?
C15 C14 H14B . . 109.9 ?
H14A C14 H14B . . 108.3 ?
C14 C13 C12 . . 111.57(16) ?
C14 C13 H13A . . 109.3 ?
C12 C13 H13A . . 109.3 ?
C14 C13 H13B . . 109.3 ?
C12 C13 H13B . . 109.3 ?
H13A C13 H13B . . 108.0 ?
C18 C19 H19A . . 109.5 ?
C18 C19 H19B . . 109.5 ?
H19A C19 H19B . . 109.5 ?
C18 C19 H19C . . 109.5 ?
H19A C19 H19C . . 109.5 ?
H19B C19 H19C . . 109.5 ?
O5 C18 C19 . . 106.16(14) ?
O5 C18 C3 . . 113.18(14) ?
C19 C18 C3 . . 110.82(14) ?
O5 C18 H18 . . 108.9 ?
C19 C18 H18 . . 108.9 ?
C3 C18 H18 . . 108.9 ?
C21 C20 C5 . . 122.45(16) ?
C21 C20 H20 . . 118.8 ?
C5 C20 H20 . . 118.8 ?
C20 C21 C22 . . 125.76(18) ?
C20 C21 H21 . . 117.1 ?
C22 C21 H21 . . 117.1 ?
C21 C22 H22A . . 109.5 ?
C21 C22 H22B . . 109.5 ?
H22A C22 H22B . . 109.5 ?
C21 C22 H22C . . 109.5 ?
H22A C22 H22C . . 109.5 ?
H22B C22 H22C . . 109.5 ?
C8 C23 H23A . . 109.5 ?
C8 C23 H23B . . 109.5 ?
H23A C23 H23B . . 109.5 ?
C8 C23 H23C . . 109.5 ?
H23A C23 H23C . . 109.5 ?
H23B C23 H23C . . 109.5 ?
C12 C24 H24A . . 109.5 ?
C12 C24 H24B . . 109.5 ?
H24A C24 H24B . . 109.5 ?
C12 C24 H24C . . 109.5 ?
H24A C24 H24C . . 109.5 ?
H24B C24 H24C . . 109.5 ?
C16 C25 H25A . . 109.5 ?
C16 C25 H25B . . 109.5 ?
H25A C25 H25B . . 109.5 ?
C16 C25 H25C . . 109.5 ?
H25A C25 H25C . . 109.5 ?
H25B C25 H25C . . 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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C17 C1 C2 O1 . . . . -62.5(2) ?
C4 C1 C2 O1 . . . . 172.93(15) ?
C6 C1 C2 O1 . . . . 57.9(2) ?
C17 C1 C2 N1 . . . . 118.69(15) ?
C4 C1 C2 N1 . . . . -5.93(16) ?
C6 C1 C2 N1 . . . . -120.94(15) ?
C5 O3 C4 O2 . . . . 90.26(15) ?
C5 O3 C4 C1 . . . . -29.97(16) ?
C5 O3 C4 C3 . . . . -142.45(13) ?
C17 C1 C4 O2 . . . . 21.25(19) ?
C2 C1 C4 O2 . . . . 143.81(13) ?
C6 C1 C4 O2 . . . . -95.76(15) ?
C17 C1 C4 O3 . . . . 141.97(13) ?
C2 C1 C4 O3 . . . . -95.47(13) ?
C6 C1 C4 O3 . . . . 24.96(15) ?
C17 C1 C4 C3 . . . . -106.52(15) ?
C2 C1 C4 C3 . . . . 16.05(15) ?
C6 C1 C4 C3 . . . . 136.47(13) ?
N1 C3 C4 O2 . . . . -144.84(14) ?
C18 C3 C4 O2 . . . . -23.1(2) ?
N1 C3 C4 O3 . . . . 90.15(14) ?
C18 C3 C4 O3 . . . . -148.07(14) ?
N1 C3 C4 C1 . . . . -19.71(16) ?
C18 C3 C4 C1 . . . . 102.07(16) ?
C4 O3 C5 C20 . . . . -106.38(15) ?
C4 O3 C5 C6 . . . . 22.60(16) ?
O1 C2 N1 C3 . . . . 173.48(15) ?
C1 C2 N1 C3 . . . . -7.69(19) ?
C18 C3 N1 C2 . . . . -107.83(16) ?
C4 C3 N1 C2 . . . . 17.38(18) ?
C17 C1 C6 C5 . . . . -135.32(13) ?
C2 C1 C6 C5 . . . . 100.66(15) ?
C4 C1 C6 C5 . . . . -12.02(15) ?
C17 C1 C6 C7 . . . . -8.51(16) ?
C2 C1 C6 C7 . . . . -132.54(14) ?
C4 C1 C6 C7 . . . . 114.79(14) ?
O3 C5 C6 C1 . . . . -5.02(15) ?
C20 C5 C6 C1 . . . . 118.68(15) ?
O3 C5 C6 C7 . . . . -123.02(14) ?
C20 C5 C6 C7 . . . . 0.7(2) ?
C1 C6 C7 C8 . . . . 148.88(14) ?
C5 C6 C7 C8 . . . . -94.01(18) ?
C1 C6 C7 C16 . . . . 24.32(16) ?
C5 C6 C7 C16 . . . . 141.43(14) ?
C12 C11 C10 C9 . . . . -178.21(14) ?
C12 C11 C10 C15 . . . . -55.67(19) ?
C15 C10 C9 C8 . . . . 15.0(3) ?
C11 C10 C9 C8 . . . . 136.85(19) ?
C10 C9 C8 C23 . . . . -178.83(18) ?
C10 C9 C8 C7 . . . . 2.8(3) ?
C16 C7 C8 C9 . . . . 13.0(2) ?
C6 C7 C8 C9 . . . . -107.55(19) ?
C16 C7 C8 C23 . . . . -165.42(16) ?
C6 C7 C8 C23 . . . . 74.0(2) ?
C10 C11 C12 C13 . . . . 53.2(2) ?
C10 C11 C12 C24 . . . . 177.05(15) ?
C2 C1 C17 O4 . . . . -64.7(2) ?
C4 C1 C17 O4 . . . . 52.6(2) ?
C6 C1 C17 O4 . . . . 170.10(16) ?
C2 C1 C17 C16 . . . . 114.24(14) ?
C4 C1 C17 C16 . . . . -128.50(15) ?
C6 C1 C17 C16 . . . . -10.97(17) ?
O4 C17 C16 C25 . . . . -32.7(2) ?
C1 C17 C16 C25 . . . . 148.40(15) ?
O4 C17 C16 C7 . . . . -155.09(17) ?
C1 C17 C16 C7 . . . . 25.99(17) ?
O4 C17 C16 C15 . . . . 91.00(19) ?
C1 C17 C16 C15 . . . . -87.91(16) ?
C8 C7 C16 C17 . . . . -155.95(13) ?
C6 C7 C16 C17 . . . . -30.43(16) ?
C8 C7 C16 C25 . . . . 82.75(18) ?
C6 C7 C16 C25 . . . . -151.73(14) ?
C8 C7 C16 C15 . . . . -44.48(18) ?
C6 C7 C16 C15 . . . . 81.04(15) ?
C9 C10 C15 C14 . . . . -177.05(15) ?
C11 C10 C15 C14 . . . . 59.55(18) ?
C9 C10 C15 C16 . . . . -47.75(19) ?
C11 C10 C15 C16 . . . . -171.16(14) ?
C17 C16 C15 C10 . . . . 173.98(14) ?
C25 C16 C15 C10 . . . . -63.56(19) ?
C7 C16 C15 C10 . . . . 63.52(16) ?
C17 C16 C15 C14 . . . . -59.91(18) ?
C25 C16 C15 C14 . . . . 62.55(19) ?
C7 C16 C15 C14 . . . . -170.38(14) ?
C10 C15 C14 C13 . . . . -61.75(18) ?
C16 C15 C14 C13 . . . . 171.66(14) ?
C15 C14 C13 C12 . . . . 59.44(19) ?
C24 C12 C13 C14 . . . . -179.30(17) ?
C11 C12 C13 C14 . . . . -54.9(2) ?
N1 C3 C18 O5 . . . . 49.40(18) ?
C4 C3 C18 O5 . . . . -66.47(19) ?
N1 C3 C18 C19 . . . . -69.72(18) ?
C4 C3 C18 C19 . . . . 174.41(14) ?
O3 C5 C20 C21 . . . . -112.44(19) ?
C6 C5 C20 C21 . . . . 126.31(19) ?
C5 C20 C21 C22 . . . . -178.4(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_ftxj20
_database_code_depnum_ccdc_archive 'CCDC 2070474'
loop_
_audit_author_name
_audit_author_address
'Tao Feng'
;South Central University for Nationalities
China
;
_audit_update_record             
;
2021-03-15 deposited with the CCDC.	2021-05-19 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H29 N O4'
_chemical_formula_iupac          ?
_chemical_formula_weight         383.47
_chemical_absolute_configuration ad

_chemical_melting_point          ?

_space_group_crystal_system      orthorhombic
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'

_cell_length_a                   6.8544(3)
_cell_length_b                   43.8920(19)
_cell_length_c                   6.7683(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2036.27(15)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9186
_cell_measurement_theta_min      6.0493
_cell_measurement_theta_max      79.0555
_cell_measurement_temperature    150.(2)

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            'light colourless'
_exptl_crystal_size_max          0.258
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.101
_exptl_crystal_density_diffrn    1.251
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             824

_exptl_absorpt_coefficient_mu    0.683
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_correction_T_min  0.77
_exptl_absorpt_correction_T_max  0.93

_exptl_special_details           
;
;

_diffrn_ambient_temperature      150.(2)

_diffrn_source                   ?
_diffrn_source_type              ?

_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_monochromator  ?

_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'


_diffrn_detector_area_resol_mean 7.3910

_diffrn_reflns_number            22455
_diffrn_reflns_av_R_equivalents  0.0597
_diffrn_reflns_av_unetI/netI     0.0503
_diffrn_reflns_theta_min         4.03
_diffrn_reflns_theta_max         79.27
_diffrn_reflns_theta_full        79.27
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measured_fraction_theta_full 0.980
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -55
_diffrn_reflns_limit_k_max       55
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       8

_refine_special_details          
;
;

_reflns_number_total             4309
_reflns_number_gt                4186
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0596
_refine_ls_R_factor_gt           0.0581
_refine_ls_wR_factor_gt          0.1584
_refine_ls_wR_factor_ref         0.1593
_refine_ls_goodness_of_fit_ref   1.110
_refine_ls_restrained_S_all      1.110
_refine_ls_number_reflns         4309
_refine_ls_number_parameters     261
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1000P)²+0.5930P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.396
_refine_diff_density_min         -0.372
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
;

Flack x determined using 1619 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.04(9)

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'

_computing_data_collection       ?
_computing_cell_refinement       'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 833)'
_computing_publication_material  ?

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 0.1725(3) 0.40211(5) 0.3853(4) 0.0345(5) Uani d . . . 1 . .
C C1 0.8485(5) 0.47304(8) 0.2839(5) 0.0360(7) Uani d . . . 1 . .
H H1A 0.803851 0.471813 0.146539 0.054 Uiso calc U . R 1 . .
H H1B 0.991447 0.473198 0.287011 0.054 Uiso calc U . R 1 . .
H H1C 0.79871 0.491783 0.344296 0.054 Uiso calc U . R 1 . .
O O2 0.5373(3) 0.42415(5) 0.1776(3) 0.0278(5) Uani d . . . 1 . .
H H2O 0.437(9) 0.4306(13) 0.113(9) 0.050(14) Uiso d . . . 1 . .
C C2 0.7729(4) 0.44550(7) 0.3988(4) 0.0242(5) Uani d . . . 1 . .
H H2 0.843551 0.42758 0.342169 0.029 Uiso calc U . R 1 . .
O O3 0.4017(3) 0.48517(5) 0.2302(3) 0.0304(5) Uani d . . . 1 . .
C C3 0.8284(4) 0.44607(7) 0.6158(4) 0.0254(5) Uani d . . . 1 . .
H H3 0.908266 0.462013 0.665423 0.031 Uiso calc U . R 1 . .
C C4 0.7651(4) 0.42422(7) 0.7371(4) 0.0250(5) Uani d . . . 1 . .
H H4 0.804783 0.423 0.871342 0.03 Uiso calc U . R 1 . .
O O4 0.3224(3) 0.44255(5) 0.8378(3) 0.0317(5) Uani d . . . 1 . .
N N1 0.3525(4) 0.47075(6) 0.5537(4) 0.0259(5) Uani d . . . 1 . .
H H1 0.293196 0.487287 0.596096 0.031 Uiso calc U . R 1 . .
C C5 0.6268(4) 0.40172(6) 0.6460(4) 0.0222(5) Uani d . . . 1 . .
H H5 0.701336 0.39003 0.544148 0.027 Uiso calc U . R 1 . .
C C6 0.5073(4) 0.37843(6) 0.7672(4) 0.0247(6) Uani d . . . 1 . .
H H6 0.449565 0.389504 0.882327 0.03 Uiso calc U . R 1 . .
C C7 0.6243(4) 0.35195(7) 0.8478(4) 0.0282(6) Uani d . . . 1 . .
C C8 0.6041(5) 0.32392(7) 0.7766(5) 0.0337(7) Uani d . . . 1 . .
H H8 0.68458 0.30841 0.83086 0.04 Uiso calc U . R 1 . .
C C9 0.4640(5) 0.31494(7) 0.6171(5) 0.0325(7) Uani d . . . 1 . .
H H9 0.345702 0.30644 0.683661 0.039 Uiso calc U . R 1 . .
C C10 0.5443(6) 0.28989(8) 0.4813(6) 0.0425(8) Uani d . . . 1 . .
H H10A 0.660162 0.29775 0.41048 0.051 Uiso calc U . R 1 . .
H H10B 0.586374 0.272353 0.56282 0.051 Uiso calc U . R 1 . .
C C16 0.3060(4) 0.39744(6) 0.4962(4) 0.0253(5) Uani d . . . 1 . .
C C15 0.3363(4) 0.36917(7) 0.6275(4) 0.0259(6) Uani d . . . 1 . .
C C14 0.3964(5) 0.34201(7) 0.4919(5) 0.0281(6) Uani d . . . 1 . .
H H14 0.510939 0.348873 0.41199 0.034 Uiso calc U . R 1 . .
C C13 0.2388(5) 0.33179(8) 0.3467(6) 0.0369(7) Uani d . . . 1 . .
H H13A 0.198754 0.349301 0.263912 0.044 Uiso calc U . R 1 . .
H H13B 0.123 0.324696 0.421013 0.044 Uiso calc U . R 1 . .
C C12 0.3129(6) 0.30604(8) 0.2137(6) 0.0410(8) Uani d . . . 1 . .
H H12A 0.204392 0.298835 0.129172 0.049 Uiso calc U . R 1 . .
H H12B 0.416395 0.314083 0.126075 0.049 Uiso calc U . R 1 . .
C C11 0.3939(7) 0.27911(8) 0.3311(6) 0.0428(8) Uani d . . . 1 . .
H H11 0.283019 0.269906 0.406229 0.051 Uiso calc U . R 1 . .
C C19 0.4287(4) 0.46803(6) 0.3672(4) 0.0234(5) Uani d . . . 1 . .
C C18 0.5504(4) 0.43889(6) 0.3615(4) 0.0218(5) Uani d . . . 1 . .
C C17 0.4707(4) 0.42034(6) 0.5370(4) 0.0216(5) Uani d . . . 1 . .
C C22 0.1504(5) 0.36303(8) 0.7459(6) 0.0347(7) Uani d . . . 1 . .
H H22A 0.040039 0.360619 0.655105 0.052 Uiso calc U . R 1 . .
H H22B 0.125268 0.380179 0.835015 0.052 Uiso calc U . R 1 . .
H H22C 0.166634 0.34434 0.823403 0.052 Uiso calc U . R 1 . .
C C23 0.3778(4) 0.44496(7) 0.6693(4) 0.0235(5) Uani d . . . 1 . .
C C21 0.4760(9) 0.25447(11) 0.1950(8) 0.0604(12) Uani d . . . 1 . .
H H21A 0.375134 0.248119 0.101014 0.091 Uiso calc U . R 1 . .
H H21B 0.517007 0.236906 0.274146 0.091 Uiso calc U . R 1 . .
H H21C 0.58837 0.262588 0.122671 0.091 Uiso calc U . R 1 . .
C C20 0.7508(5) 0.35853(8) 1.0247(5) 0.0321(6) Uani d . . . 1 . .
H H20A 0.828775 0.340473 1.056498 0.048 Uiso calc U . R 1 . .
H H20B 0.668097 0.363761 1.137864 0.048 Uiso calc U . R 1 . .
H H20C 0.837751 0.375645 0.99487 0.048 Uiso calc U . R 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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C16 . 1.201(4) ?
C1 C2 . 1.528(4) ?
C1 H1A . 0.98 ?
C1 H1B . 0.98 ?
C1 H1C . 0.98 ?
O2 C18 . 1.406(3) ?
O2 H2O . 0.87(6) ?
C2 C3 . 1.517(4) ?
C2 C18 . 1.573(4) ?
C2 H2 . 1.0 ?
O3 C19 . 1.208(4) ?
C3 C4 . 1.335(4) ?
C3 H3 . 0.95 ?
C4 C5 . 1.502(4) ?
C4 H4 . 0.95 ?
O4 C23 . 1.206(4) ?
N1 C19 . 1.372(4) ?
N1 C23 . 1.387(4) ?
N1 H1 . 0.88 ?
C5 C17 . 1.535(4) ?
C5 C6 . 1.545(4) ?
C5 H5 . 1.0 ?
C6 C7 . 1.514(4) ?
C6 C15 . 1.560(4) ?
C6 H6 . 1.0 ?
C7 C8 . 1.329(5) ?
C7 C20 . 1.506(5) ?
C8 C9 . 1.498(5) ?
C8 H8 . 0.95 ?
C9 C14 . 1.531(4) ?
C9 C10 . 1.535(5) ?
C9 H9 . 1.0 ?
C10 C11 . 1.523(6) ?
C10 H10A . 0.99 ?
C10 H10B . 0.99 ?
C16 C17 . 1.537(4) ?
C16 C15 . 1.540(4) ?
C15 C22 . 1.529(4) ?
C15 C14 . 1.560(4) ?
C14 C13 . 1.528(5) ?
C14 H14 . 1.0 ?
C13 C12 . 1.531(5) ?
C13 H13A . 0.99 ?
C13 H13B . 0.99 ?
C12 C11 . 1.529(5) ?
C12 H12A . 0.99 ?
C12 H12B . 0.99 ?
C11 C21 . 1.528(5) ?
C11 H11 . 1.0 ?
C19 C18 . 1.528(4) ?
C18 C17 . 1.540(4) ?
C17 C23 . 1.541(4) ?
C22 H22A . 0.98 ?
C22 H22B . 0.98 ?
C22 H22C . 0.98 ?
C21 H21A . 0.98 ?
C21 H21B . 0.98 ?
C21 H21C . 0.98 ?
C20 H20A . 0.98 ?
C20 H20B . 0.98 ?
C20 H20C . 0.98 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 C1 H1A . . 109.5 ?
C2 C1 H1B . . 109.5 ?
H1A C1 H1B . . 109.5 ?
C2 C1 H1C . . 109.5 ?
H1A C1 H1C . . 109.5 ?
H1B C1 H1C . . 109.5 ?
C18 O2 H2O . . 110.(4) ?
C3 C2 C1 . . 113.3(3) ?
C3 C2 C18 . . 113.7(2) ?
C1 C2 C18 . . 113.1(2) ?
C3 C2 H2 . . 105.2 ?
C1 C2 H2 . . 105.2 ?
C18 C2 H2 . . 105.2 ?
C4 C3 C2 . . 120.1(3) ?
C4 C3 H3 . . 119.9 ?
C2 C3 H3 . . 119.9 ?
C3 C4 C5 . . 115.2(3) ?
C3 C4 H4 . . 122.4 ?
C5 C4 H4 . . 122.4 ?
C19 N1 C23 . . 113.6(2) ?
C19 N1 H1 . . 123.2 ?
C23 N1 H1 . . 123.2 ?
C4 C5 C17 . . 106.7(2) ?
C4 C5 C6 . . 123.5(2) ?
C17 C5 C6 . . 103.8(2) ?
C4 C5 H5 . . 107.3 ?
C17 C5 H5 . . 107.3 ?
C6 C5 H5 . . 107.3 ?
C7 C6 C5 . . 114.7(2) ?
C7 C6 C15 . . 114.6(3) ?
C5 C6 C15 . . 104.4(2) ?
C7 C6 H6 . . 107.6 ?
C5 C6 H6 . . 107.6 ?
C15 C6 H6 . . 107.6 ?
C8 C7 C20 . . 121.8(3) ?
C8 C7 C6 . . 121.6(3) ?
C20 C7 C6 . . 116.4(3) ?
C7 C8 C9 . . 124.9(3) ?
C7 C8 H8 . . 117.5 ?
C9 C8 H8 . . 117.5 ?
C8 C9 C14 . . 112.9(3) ?
C8 C9 C10 . . 113.0(3) ?
C14 C9 C10 . . 109.5(3) ?
C8 C9 H9 . . 107.1 ?
C14 C9 H9 . . 107.1 ?
C10 C9 H9 . . 107.1 ?
C11 C10 C9 . . 112.3(3) ?
C11 C10 H10A . . 109.1 ?
C9 C10 H10A . . 109.1 ?
C11 C10 H10B . . 109.1 ?
C9 C10 H10B . . 109.1 ?
H10A C10 H10B . . 107.9 ?
O1 C16 C17 . . 124.1(3) ?
O1 C16 C15 . . 126.9(3) ?
C17 C16 C15 . . 108.9(2) ?
C22 C15 C16 . . 109.4(2) ?
C22 C15 C14 . . 113.2(3) ?
C16 C15 C14 . . 108.2(2) ?
C22 C15 C6 . . 110.8(3) ?
C16 C15 C6 . . 103.9(2) ?
C14 C15 C6 . . 110.9(2) ?
C13 C14 C9 . . 110.0(3) ?
C13 C14 C15 . . 114.6(3) ?
C9 C14 C15 . . 110.4(2) ?
C13 C14 H14 . . 107.2 ?
C9 C14 H14 . . 107.2 ?
C15 C14 H14 . . 107.2 ?
C14 C13 C12 . . 111.1(3) ?
C14 C13 H13A . . 109.4 ?
C12 C13 H13A . . 109.4 ?
C14 C13 H13B . . 109.4 ?
C12 C13 H13B . . 109.4 ?
H13A C13 H13B . . 108.0 ?
C11 C12 C13 . . 112.7(3) ?
C11 C12 H12A . . 109.1 ?
C13 C12 H12A . . 109.1 ?
C11 C12 H12B . . 109.1 ?
C13 C12 H12B . . 109.1 ?
H12A C12 H12B . . 107.8 ?
C10 C11 C21 . . 111.9(4) ?
C10 C11 C12 . . 110.7(3) ?
C21 C11 C12 . . 111.6(4) ?
C10 C11 H11 . . 107.5 ?
C21 C11 H11 . . 107.5 ?
C12 C11 H11 . . 107.5 ?
O3 C19 N1 . . 126.5(3) ?
O3 C19 C18 . . 125.8(3) ?
N1 C19 C18 . . 107.7(2) ?
O2 C18 C19 . . 111.9(2) ?
O2 C18 C17 . . 114.7(2) ?
C19 C18 C17 . . 103.3(2) ?
O2 C18 C2 . . 106.8(2) ?
C19 C18 C2 . . 111.8(2) ?
C17 C18 C2 . . 108.5(2) ?
C5 C17 C16 . . 104.5(2) ?
C5 C17 C18 . . 113.9(2) ?
C16 C17 C18 . . 117.9(2) ?
C5 C17 C23 . . 112.4(2) ?
C16 C17 C23 . . 105.0(2) ?
C18 C17 C23 . . 102.9(2) ?
C15 C22 H22A . . 109.5 ?
C15 C22 H22B . . 109.5 ?
H22A C22 H22B . . 109.5 ?
C15 C22 H22C . . 109.5 ?
H22A C22 H22C . . 109.5 ?
H22B C22 H22C . . 109.5 ?
O4 C23 N1 . . 124.4(3) ?
O4 C23 C17 . . 128.1(3) ?
N1 C23 C17 . . 107.2(2) ?
C11 C21 H21A . . 109.5 ?
C11 C21 H21B . . 109.5 ?
H21A C21 H21B . . 109.5 ?
C11 C21 H21C . . 109.5 ?
H21A C21 H21C . . 109.5 ?
H21B C21 H21C . . 109.5 ?
C7 C20 H20A . . 109.5 ?
C7 C20 H20B . . 109.5 ?
H20A C20 H20B . . 109.5 ?
C7 C20 H20C . . 109.5 ?
H20A C20 H20C . . 109.5 ?
H20B C20 H20C . . 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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C1 C2 C3 C4 . . . . 176.9(3) ?
C18 C2 C3 C4 . . . . 46.0(4) ?
C2 C3 C4 C5 . . . . -4.8(4) ?
C3 C4 C5 C17 . . . . -48.5(3) ?
C3 C4 C5 C6 . . . . -168.3(3) ?
C4 C5 C6 C7 . . . . -74.0(3) ?
C17 C5 C6 C7 . . . . 164.9(2) ?
C4 C5 C6 C15 . . . . 159.7(2) ?
C17 C5 C6 C15 . . . . 38.6(3) ?
C5 C6 C7 C8 . . . . -109.3(3) ?
C15 C6 C7 C8 . . . . 11.5(4) ?
C5 C6 C7 C20 . . . . 76.1(3) ?
C15 C6 C7 C20 . . . . -163.1(2) ?
C20 C7 C8 C9 . . . . 172.5(3) ?
C6 C7 C8 C9 . . . . -1.8(5) ?
C7 C8 C9 C14 . . . . 20.3(4) ?
C7 C8 C9 C10 . . . . 145.2(3) ?
C8 C9 C10 C11 . . . . 175.1(3) ?
C14 C9 C10 C11 . . . . -58.2(4) ?
O1 C16 C15 C22 . . . . -50.8(4) ?
C17 C16 C15 C22 . . . . 126.1(3) ?
O1 C16 C15 C14 . . . . 72.9(4) ?
C17 C16 C15 C14 . . . . -110.2(3) ?
O1 C16 C15 C6 . . . . -169.2(3) ?
C17 C16 C15 C6 . . . . 7.8(3) ?
C7 C6 C15 C22 . . . . 87.9(3) ?
C5 C6 C15 C22 . . . . -145.7(2) ?
C7 C6 C15 C16 . . . . -154.7(2) ?
C5 C6 C15 C16 . . . . -28.3(3) ?
C7 C6 C15 C14 . . . . -38.6(3) ?
C5 C6 C15 C14 . . . . 87.8(3) ?
C8 C9 C14 C13 . . . . -174.2(3) ?
C10 C9 C14 C13 . . . . 59.0(4) ?
C8 C9 C14 C15 . . . . -46.8(3) ?
C10 C9 C14 C15 . . . . -173.6(3) ?
C22 C15 C14 C13 . . . . 56.0(4) ?
C16 C15 C14 C13 . . . . -65.4(3) ?
C6 C15 C14 C13 . . . . -178.8(3) ?
C22 C15 C14 C9 . . . . -68.8(3) ?
C16 C15 C14 C9 . . . . 169.8(2) ?
C6 C15 C14 C9 . . . . 56.4(3) ?
C9 C14 C13 C12 . . . . -57.5(4) ?
C15 C14 C13 C12 . . . . 177.5(3) ?
C14 C13 C12 C11 . . . . 54.2(4) ?
C9 C10 C11 C21 . . . . 179.3(3) ?
C9 C10 C11 C12 . . . . 54.1(4) ?
C13 C12 C11 C10 . . . . -51.8(4) ?
C13 C12 C11 C21 . . . . -177.2(4) ?
C23 N1 C19 O3 . . . . 168.5(3) ?
C23 N1 C19 C18 . . . . -10.1(3) ?
O3 C19 C18 O2 . . . . -34.3(4) ?
N1 C19 C18 O2 . . . . 144.3(2) ?
O3 C19 C18 C17 . . . . -158.2(3) ?
N1 C19 C18 C17 . . . . 20.5(3) ?
O3 C19 C18 C2 . . . . 85.4(3) ?
N1 C19 C18 C2 . . . . -96.0(3) ?
C3 C2 C18 O2 . . . . -150.7(2) ?
C1 C2 C18 O2 . . . . 78.3(3) ?
C3 C2 C18 C19 . . . . 86.6(3) ?
C1 C2 C18 C19 . . . . -44.4(3) ?
C3 C2 C18 C17 . . . . -26.6(3) ?
C1 C2 C18 C17 . . . . -157.6(2) ?
C4 C5 C17 C16 . . . . -165.1(2) ?
C6 C5 C17 C16 . . . . -33.3(3) ?
C4 C5 C17 C18 . . . . 64.9(3) ?
C6 C5 C17 C18 . . . . -163.3(2) ?
C4 C5 C17 C23 . . . . -51.7(3) ?
C6 C5 C17 C23 . . . . 80.1(3) ?
O1 C16 C17 C5 . . . . -167.2(3) ?
C15 C16 C17 C5 . . . . 15.8(3) ?
O1 C16 C17 C18 . . . . -39.5(4) ?
C15 C16 C17 C18 . . . . 143.4(2) ?
O1 C16 C17 C23 . . . . 74.3(4) ?
C15 C16 C17 C23 . . . . -102.7(2) ?
O2 C18 C17 C5 . . . . 93.9(3) ?
C19 C18 C17 C5 . . . . -144.1(2) ?
C2 C18 C17 C5 . . . . -25.4(3) ?
O2 C18 C17 C16 . . . . -29.1(3) ?
C19 C18 C17 C16 . . . . 92.9(3) ?
C2 C18 C17 C16 . . . . -148.4(2) ?
O2 C18 C17 C23 . . . . -144.1(2) ?
C19 C18 C17 C23 . . . . -22.1(3) ?
C2 C18 C17 C23 . . . . 96.6(2) ?
C19 N1 C23 O4 . . . . 179.8(3) ?
C19 N1 C23 C17 . . . . -4.9(3) ?
C5 C17 C23 O4 . . . . -44.6(4) ?
C16 C17 C23 O4 . . . . 68.5(4) ?
C18 C17 C23 O4 . . . . -167.6(3) ?
C5 C17 C23 N1 . . . . 140.4(2) ?
C16 C17 C23 N1 . . . . -106.6(3) ?
C18 C17 C23 N1 . . . . 17.3(3) ?

