# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2023

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

data_asp1
_database_code_depnum_ccdc_archive 'CCDC 2241778'
loop_
_audit_author_name
_audit_author_address
'Yu-Rong Yang'
;Kunming Institute of Botany
China
;
_audit_update_record             
;
2023-02-14 deposited with the CCDC.	2023-04-17 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C20 H23 N O5'
_chemical_formula_sum            'C20 H23 N O5'
_chemical_formula_iupac          ?
_chemical_formula_weight         357.39
_chemical_absolute_configuration rmad

_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                   11.0160(2)
_cell_length_b                   11.7054(3)
_cell_length_c                   13.6481(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1759.88(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9933
_cell_measurement_theta_min      3.2381
_cell_measurement_theta_max      72.1989
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       block
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_size_max          0.550
_exptl_crystal_size_mid          0.440
_exptl_crystal_size_min          0.330
_exptl_crystal_density_diffrn    1.349
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             760

_exptl_absorpt_coefficient_mu    0.797
_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  0.65
_exptl_absorpt_correction_T_max  0.78

_exptl_special_details           
;
;

_diffrn_ambient_temperature      100.(2)

_diffrn_source                   'Ius Diamond'
_diffrn_source_type              Microfocus

_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_monochromator  'Helixos MX multilayer Optic'

_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON II'
_diffrn_measurement_method       ?

_diffrn_detector_area_resol_mean 7.3910

_diffrn_reflns_number            11329
_diffrn_reflns_av_R_equivalents  0.0360
_diffrn_reflns_av_unetI/netI     0.0303
_diffrn_reflns_theta_min         5.16
_diffrn_reflns_theta_max         72.19
_diffrn_reflns_theta_full        72.19
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       16

_refine_special_details          
;
;

_reflns_number_total             3426
_reflns_number_gt                3394
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0339
_refine_ls_R_factor_gt           0.0337
_refine_ls_wR_factor_gt          0.0896
_refine_ls_wR_factor_ref         0.0898
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_restrained_S_all      1.081
_refine_ls_number_reflns         3426
_refine_ls_number_parameters     237
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0463P)²+0.5630P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_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         0.677
_refine_diff_density_min         -0.183
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
;

Flack x determined using 1411 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.09(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       'Bruker Instrument Service vV6.2.9'
_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-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 882)'
_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 0.09720(13) 0.39691(13) 0.36794(11) 0.0199(3) Uani d . . . 1 . .
O O2 0.33679(14) 0.84802(13) 0.48049(12) 0.0222(3) Uani d . . . 1 . .
O O3 0.52819(14) 0.79645(13) 0.53551(11) 0.0218(3) Uani d . . . 1 . .
O O4 0.10454(13) 0.30420(13) 0.22125(11) 0.0206(3) Uani d . . . 1 . .
O O5 0.57698(15) 0.63830(15) 0.13645(13) 0.0286(4) Uani d . . . 1 . .
N N1 0.46746(16) 0.48241(15) 0.18912(13) 0.0173(4) Uani d . . . 1 . .
C C1 -0.0230(2) 0.2266(2) 0.3505(2) 0.0312(5) Uani d . . . 1 . .
H H8 -0.071767 0.181631 0.304469 0.047 Uiso calc U . R 1 . .
H H7 -0.073558 0.24948 0.406257 0.047 Uiso calc U . R 1 . .
H H1 0.045242 0.180391 0.373956 0.047 Uiso calc U . R 1 . .
C C2 0.0249(2) 0.33212(19) 0.29933(17) 0.0211(5) Uani d . . . 1 . .
C C3 0.22283(18) 0.38120(17) 0.34279(14) 0.0162(4) Uani d . . . 1 . .
H H21 0.272005 0.358288 0.401161 0.019 Uiso calc U . R 1 . .
C C4 0.27572(18) 0.48860(17) 0.29286(14) 0.0150(4) Uani d . . . 1 . .
H H22 0.204238 0.535259 0.271922 0.018 Uiso calc U . R 1 . .
C C5 0.35040(18) 0.56541(17) 0.35912(14) 0.0141(4) Uani d . . . 1 . .
C C6 0.29980(18) 0.67071(18) 0.38678(15) 0.0154(4) Uani d . . . 1 . .
H H3 0.222038 0.693366 0.3638 0.018 Uiso calc U . R 1 . .
C C7 0.36577(18) 0.73987(18) 0.44784(15) 0.0158(4) Uani d . . . 1 . .
C C8 0.4322(2) 0.87776(19) 0.54733(16) 0.0209(5) Uani d . . . 1 . .
H H2 0.462257 0.955727 0.533103 0.025 Uiso calc U . R 1 . .
H H23 0.401667 0.876086 0.615531 0.025 Uiso calc U . R 1 . .
C C9 0.47892(19) 0.70876(18) 0.48123(15) 0.0170(4) Uani d . . . 1 . .
C C10 -0.0752(2) 0.4069(2) 0.2583(2) 0.0290(5) Uani d . . . 1 . .
H H4 -0.040301 0.478517 0.234041 0.044 Uiso calc U . R 1 . .
H H5 -0.134333 0.423658 0.310034 0.044 Uiso calc U . R 1 . .
H H6 -0.115785 0.366932 0.204403 0.044 Uiso calc U . R 1 . .
C C11 0.22241(18) 0.28768(18) 0.26464(15) 0.0182(4) Uani d . . . 1 . .
H H20 0.232095 0.209633 0.29339 0.022 Uiso calc U . R 1 . .
C C12 0.32191(19) 0.31610(18) 0.19204(16) 0.0194(4) Uani d . . . 1 . .
H H9 0.298428 0.2914 0.125299 0.023 Uiso calc U . R 1 . .
H H10 0.398312 0.277007 0.210334 0.023 Uiso calc U . R 1 . .
C C13 0.33884(18) 0.44727(18) 0.19541(15) 0.0164(4) Uani d . . . 1 . .
C C14 0.2869(2) 0.51014(19) 0.10576(15) 0.0193(4) Uani d . . . 1 . .
H H18 0.300468 0.465896 0.044917 0.023 Uiso calc U . R 1 . .
H H19 0.198918 0.524659 0.113536 0.023 Uiso calc U . R 1 . .
C C15 0.3587(2) 0.6219(2) 0.10461(16) 0.0218(5) Uani d . . . 1 . .
H H11 0.36546 0.652934 0.037364 0.026 Uiso calc U . R 1 . .
H H12 0.320762 0.67992 0.147549 0.026 Uiso calc U . R 1 . .
C C16 0.4821(2) 0.58522(18) 0.14381(16) 0.0204(4) Uani d . . . 1 . .
C C17 0.56272(19) 0.4339(2) 0.25004(16) 0.0208(4) Uani d . . . 1 . .
H H17 0.636065 0.482521 0.245506 0.025 Uiso calc U . R 1 . .
H H13 0.583989 0.357066 0.225134 0.025 Uiso calc U . R 1 . .
C C18 0.5238(2) 0.42444(18) 0.35791(16) 0.0192(4) Uani d . . . 1 . .
H H16 0.465472 0.360643 0.365177 0.023 Uiso calc U . R 1 . .
H H14 0.595706 0.407171 0.398813 0.023 Uiso calc U . R 1 . .
C C19 0.46572(18) 0.53357(18) 0.39335(15) 0.0154(4) Uani d . . . 1 . .
C C20 0.53136(19) 0.60690(18) 0.45592(15) 0.0178(4) Uani d . . . 1 . .
H H15 0.609389 0.586302 0.47972 0.021 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 C3 . 1.438(2) ?
O1 C2 . 1.444(3) ?
O2 C7 . 1.380(3) ?
O2 C8 . 1.435(3) ?
O3 C9 . 1.377(2) ?
O3 C8 . 1.432(3) ?
O4 C2 . 1.418(3) ?
O4 C11 . 1.440(2) ?
O5 C16 . 1.220(3) ?
N1 C16 . 1.363(3) ?
N1 C17 . 1.454(3) ?
N1 C13 . 1.478(3) ?
C1 C2 . 1.514(3) ?
C1 H8 . 0.98 ?
C1 H7 . 0.98 ?
C1 H1 . 0.98 ?
C2 C10 . 1.515(3) ?
C3 C11 . 1.528(3) ?
C3 C4 . 1.544(3) ?
C3 H21 . 1.0 ?
C4 C5 . 1.518(3) ?
C4 C13 . 1.577(3) ?
C4 H22 . 1.0 ?
C5 C19 . 1.404(3) ?
C5 C6 . 1.404(3) ?
C6 C7 . 1.370(3) ?
C6 H3 . 0.95 ?
C7 C9 . 1.376(3) ?
C8 H2 . 0.99 ?
C8 H23 . 0.99 ?
C9 C20 . 1.369(3) ?
C10 H4 . 0.98 ?
C10 H5 . 0.98 ?
C10 H6 . 0.98 ?
C11 C12 . 1.515(3) ?
C11 H20 . 1.0 ?
C12 C13 . 1.547(3) ?
C12 H9 . 0.99 ?
C12 H10 . 0.99 ?
C13 C14 . 1.538(3) ?
C14 C15 . 1.528(3) ?
C14 H18 . 0.99 ?
C14 H19 . 0.99 ?
C15 C16 . 1.522(3) ?
C15 H11 . 0.99 ?
C15 H12 . 0.99 ?
C17 C18 . 1.537(3) ?
C17 H17 . 0.99 ?
C17 H13 . 0.99 ?
C18 C19 . 1.508(3) ?
C18 H16 . 0.99 ?
C18 H14 . 0.99 ?
C19 C20 . 1.410(3) ?
C20 H15 . 0.95 ?

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
C3 O1 C2 . . 107.99(15) ?
C7 O2 C8 . . 104.98(16) ?
C9 O3 C8 . . 105.37(16) ?
C2 O4 C11 . . 106.24(16) ?
C16 N1 C17 . . 121.26(18) ?
C16 N1 C13 . . 112.67(17) ?
C17 N1 C13 . . 123.37(17) ?
C2 C1 H8 . . 109.5 ?
C2 C1 H7 . . 109.5 ?
H8 C1 H7 . . 109.5 ?
C2 C1 H1 . . 109.5 ?
H8 C1 H1 . . 109.5 ?
H7 C1 H1 . . 109.5 ?
O4 C2 O1 . . 105.49(16) ?
O4 C2 C1 . . 111.98(19) ?
O1 C2 C1 . . 108.75(19) ?
O4 C2 C10 . . 107.81(19) ?
O1 C2 C10 . . 109.72(18) ?
C1 C2 C10 . . 112.8(2) ?
O1 C3 C11 . . 104.79(16) ?
O1 C3 C4 . . 111.37(16) ?
C11 C3 C4 . . 106.04(16) ?
O1 C3 H21 . . 111.4 ?
C11 C3 H21 . . 111.4 ?
C4 C3 H21 . . 111.4 ?
C5 C4 C3 . . 115.08(16) ?
C5 C4 C13 . . 116.45(16) ?
C3 C4 C13 . . 106.78(16) ?
C5 C4 H22 . . 105.9 ?
C3 C4 H22 . . 105.9 ?
C13 C4 H22 . . 105.9 ?
C19 C5 C6 . . 120.18(19) ?
C19 C5 C4 . . 122.11(18) ?
C6 C5 C4 . . 117.71(18) ?
C7 C6 C5 . . 118.12(19) ?
C7 C6 H3 . . 120.9 ?
C5 C6 H3 . . 120.9 ?
C6 C7 C9 . . 121.7(2) ?
C6 C7 O2 . . 128.01(19) ?
C9 C7 O2 . . 110.21(18) ?
O3 C8 O2 . . 107.95(16) ?
O3 C8 H2 . . 110.1 ?
O2 C8 H2 . . 110.1 ?
O3 C8 H23 . . 110.1 ?
O2 C8 H23 . . 110.1 ?
H2 C8 H23 . . 108.4 ?
C20 C9 C7 . . 121.9(2) ?
C20 C9 O3 . . 128.2(2) ?
C7 C9 O3 . . 109.75(19) ?
C2 C10 H4 . . 109.5 ?
C2 C10 H5 . . 109.5 ?
H4 C10 H5 . . 109.5 ?
C2 C10 H6 . . 109.5 ?
H4 C10 H6 . . 109.5 ?
H5 C10 H6 . . 109.5 ?
O4 C11 C12 . . 110.73(17) ?
O4 C11 C3 . . 101.16(16) ?
C12 C11 C3 . . 107.28(17) ?
O4 C11 H20 . . 112.3 ?
C12 C11 H20 . . 112.3 ?
C3 C11 H20 . . 112.3 ?
C11 C12 C13 . . 106.60(17) ?
C11 C12 H9 . . 110.4 ?
C13 C12 H9 . . 110.4 ?
C11 C12 H10 . . 110.4 ?
C13 C12 H10 . . 110.4 ?
H9 C12 H10 . . 108.6 ?
N1 C13 C14 . . 100.20(16) ?
N1 C13 C12 . . 112.95(17) ?
C14 C13 C12 . . 113.97(17) ?
N1 C13 C4 . . 112.73(16) ?
C14 C13 C4 . . 111.12(16) ?
C12 C13 C4 . . 106.05(17) ?
C15 C14 C13 . . 103.01(17) ?
C15 C14 H18 . . 111.2 ?
C13 C14 H18 . . 111.2 ?
C15 C14 H19 . . 111.2 ?
C13 C14 H19 . . 111.2 ?
H18 C14 H19 . . 109.1 ?
C16 C15 C14 . . 102.54(18) ?
C16 C15 H11 . . 111.3 ?
C14 C15 H11 . . 111.3 ?
C16 C15 H12 . . 111.3 ?
C14 C15 H12 . . 111.3 ?
H11 C15 H12 . . 109.2 ?
O5 C16 N1 . . 126.0(2) ?
O5 C16 C15 . . 126.3(2) ?
N1 C16 C15 . . 107.65(18) ?
N1 C17 C18 . . 111.99(17) ?
N1 C17 H17 . . 109.2 ?
C18 C17 H17 . . 109.2 ?
N1 C17 H13 . . 109.2 ?
C18 C17 H13 . . 109.2 ?
H17 C17 H13 . . 107.9 ?
C19 C18 C17 . . 111.35(18) ?
C19 C18 H16 . . 109.4 ?
C17 C18 H16 . . 109.4 ?
C19 C18 H14 . . 109.4 ?
C17 C18 H14 . . 109.4 ?
H16 C18 H14 . . 108.0 ?
C5 C19 C20 . . 120.26(19) ?
C5 C19 C18 . . 120.13(18) ?
C20 C19 C18 . . 119.48(19) ?
C9 C20 C19 . . 117.8(2) ?
C9 C20 H15 . . 121.1 ?
C19 C20 H15 . . 121.1 ?

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
C11 O4 C2 O1 . . . . 33.9(2) ?
C11 O4 C2 C1 . . . . -84.2(2) ?
C11 O4 C2 C10 . . . . 151.09(18) ?
C3 O1 C2 O4 . . . . -14.7(2) ?
C3 O1 C2 C1 . . . . 105.6(2) ?
C3 O1 C2 C10 . . . . -130.6(2) ?
C2 O1 C3 C11 . . . . -8.7(2) ?
C2 O1 C3 C4 . . . . 105.51(18) ?
O1 C3 C4 C5 . . . . 100.20(19) ?
C11 C3 C4 C5 . . . . -146.36(17) ?
O1 C3 C4 C13 . . . . -128.90(16) ?
C11 C3 C4 C13 . . . . -15.5(2) ?
C3 C4 C5 C19 . . . . 71.2(2) ?
C13 C4 C5 C19 . . . . -54.9(3) ?
C3 C4 C5 C6 . . . . -108.1(2) ?
C13 C4 C5 C6 . . . . 125.8(2) ?
C19 C5 C6 C7 . . . . -0.3(3) ?
C4 C5 C6 C7 . . . . 178.99(17) ?
C5 C6 C7 C9 . . . . 0.5(3) ?
C5 C6 C7 O2 . . . . 176.75(19) ?
C8 O2 C7 C6 . . . . 176.1(2) ?
C8 O2 C7 C9 . . . . -7.3(2) ?
C9 O3 C8 O2 . . . . -13.2(2) ?
C7 O2 C8 O3 . . . . 12.6(2) ?
C6 C7 C9 C20 . . . . -0.5(3) ?
O2 C7 C9 C20 . . . . -177.34(18) ?
C6 C7 C9 O3 . . . . 175.92(18) ?
O2 C7 C9 O3 . . . . -0.9(2) ?
C8 O3 C9 C20 . . . . -175.1(2) ?
C8 O3 C9 C7 . . . . 8.8(2) ?
C2 O4 C11 C12 . . . . -151.55(17) ?
C2 O4 C11 C3 . . . . -38.07(19) ?
O1 C3 C11 O4 . . . . 28.2(2) ?
C4 C3 C11 O4 . . . . -89.75(17) ?
O1 C3 C11 C12 . . . . 144.21(17) ?
C4 C3 C11 C12 . . . . 26.3(2) ?
O4 C11 C12 C13 . . . . 82.7(2) ?
C3 C11 C12 C13 . . . . -26.8(2) ?
C16 N1 C13 C14 . . . . 27.2(2) ?
C17 N1 C13 C14 . . . . -171.30(18) ?
C16 N1 C13 C12 . . . . 148.80(18) ?
C17 N1 C13 C12 . . . . -49.7(3) ?
C16 N1 C13 C4 . . . . -91.0(2) ?
C17 N1 C13 C4 . . . . 70.5(2) ?
C11 C12 C13 N1 . . . . 140.57(17) ?
C11 C12 C13 C14 . . . . -105.9(2) ?
C11 C12 C13 C4 . . . . 16.6(2) ?
C5 C4 C13 N1 . . . . 5.5(3) ?
C3 C4 C13 N1 . . . . -124.67(17) ?
C5 C4 C13 C14 . . . . -106.1(2) ?
C3 C4 C13 C14 . . . . 123.76(18) ?
C5 C4 C13 C12 . . . . 129.54(19) ?
C3 C4 C13 C12 . . . . -0.6(2) ?
N1 C13 C14 C15 . . . . -36.1(2) ?
C12 C13 C14 C15 . . . . -157.01(17) ?
C4 C13 C14 C15 . . . . 83.3(2) ?
C13 C14 C15 C16 . . . . 33.3(2) ?
C17 N1 C16 O5 . . . . 11.3(3) ?
C13 N1 C16 O5 . . . . 173.3(2) ?
C17 N1 C16 C15 . . . . -168.40(18) ?
C13 N1 C16 C15 . . . . -6.4(2) ?
C14 C15 C16 O5 . . . . 162.8(2) ?
C14 C15 C16 N1 . . . . -17.5(2) ?
C16 N1 C17 C18 . . . . 115.2(2) ?
C13 N1 C17 C18 . . . . -44.8(3) ?
N1 C17 C18 C19 . . . . -47.0(2) ?
C6 C5 C19 C20 . . . . 0.2(3) ?
C4 C5 C19 C20 . . . . -179.13(18) ?
C6 C5 C19 C18 . . . . -175.61(18) ?
C4 C5 C19 C18 . . . . 5.1(3) ?
C17 C18 C19 C5 . . . . 70.6(2) ?
C17 C18 C19 C20 . . . . -105.3(2) ?
C7 C9 C20 C19 . . . . 0.3(3) ?
O3 C9 C20 C19 . . . . -175.39(19) ?
C5 C19 C20 C9 . . . . -0.1(3) ?
C18 C19 C20 C9 . . . . 175.67(18) ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
C6 H3 O3 2_466 0.95 2.54 3.198(2) 126.3 ?
C8 H2 O1 2_566 0.99 2.65 3.405(3) 133.5 ?
C8 H23 O4 4_565 0.99 2.56 3.215(3) 123.8 ?
C11 H20 O5 3_645 1.00 2.46 3.125(3) 123.7 ?
C12 H10 O5 3_645 0.99 2.66 3.324(3) 124.6 ?
C15 H11 O1 4_564 0.99 2.42 3.274(3) 144.1 ?
C18 H16 O5 3_645 0.99 2.64 3.529(3) 148.9 ?

####################################################################### 
# 
# 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_au3114
_database_code_depnum_ccdc_archive 'CCDC 2241779'
loop_
_audit_author_name
_audit_author_address
'Yu-Rong Yang'
;Kunming Institute of Botany
China
;
_audit_update_record             
;
2023-02-14 deposited with the CCDC.	2023-04-17 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C16 H16 F3 N O4'
_chemical_formula_sum            'C16 H16 F3 N O4'
_chemical_formula_iupac          ?
_chemical_formula_weight         343.30
_chemical_absolute_configuration rmad

_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                   7.1715(3)
_cell_length_b                   9.3959(4)
_cell_length_c                   23.0426(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1552.67(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9888
_cell_measurement_theta_min      4.7063
_cell_measurement_theta_max      72.3291
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       block
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_size_max          0.750
_exptl_crystal_size_mid          0.600
_exptl_crystal_size_min          0.320
_exptl_crystal_density_diffrn    1.469
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             712

_exptl_absorpt_coefficient_mu    1.116
_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  0.45
_exptl_absorpt_correction_T_max  0.72

_exptl_special_details           
;
;

_diffrn_ambient_temperature      100.(2)

_diffrn_source                   'Ius Diamond'
_diffrn_source_type              Microfocus

_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_monochromator  'Helixos MX multilayer Optic'

_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON II'
_diffrn_measurement_method       ?

_diffrn_detector_area_resol_mean 7.3910

_diffrn_reflns_number            15643
_diffrn_reflns_av_R_equivalents  0.0541
_diffrn_reflns_av_unetI/netI     0.0330
_diffrn_reflns_theta_min         5.08
_diffrn_reflns_theta_max         72.43
_diffrn_reflns_theta_full        72.43
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       28

_refine_special_details          
;
;

_reflns_number_total             3052
_reflns_number_gt                3022
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0318
_refine_ls_R_factor_gt           0.0315
_refine_ls_wR_factor_gt          0.0799
_refine_ls_wR_factor_ref         0.0802
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_restrained_S_all      1.062
_refine_ls_number_reflns         3052
_refine_ls_number_parameters     218
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0418P)²+0.3544P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_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         0.267
_refine_diff_density_min         -0.286
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
;

Flack x determined using 1238 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.02(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'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       'Bruker Instrument Service vV6.2.9'
_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-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 882)'
_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
F F1 0.1133(3) 0.71463(15) 0.56442(6) 0.0536(5) Uani d . . . 1 . .
F F2 -0.09575(18) 0.74933(14) 0.63005(7) 0.0419(4) Uani d . . . 1 . .
F F3 0.1367(2) 0.89264(12) 0.62212(6) 0.0348(3) Uani d . . . 1 . .
O O1 0.6851(2) 0.13925(17) 0.51843(6) 0.0337(4) Uani d . . . 1 . .
O O2 0.3046(2) 0.72994(14) 0.69646(6) 0.0279(3) Uani d . . . 1 . .
O O3 0.4550(2) 0.52624(15) 0.78087(6) 0.0254(3) Uani d . . . 1 . .
O O4 0.1471(2) 0.53570(17) 0.79525(6) 0.0319(4) Uani d . . . 1 . .
N N1 0.1750(2) 0.52702(16) 0.66152(6) 0.0178(3) Uani d . . . 1 . .
C C1 0.0874(3) 0.7575(2) 0.61917(9) 0.0285(4) Uani d . . . 1 . .
C C2 0.2006(3) 0.6677(2) 0.66296(8) 0.0213(4) Uani d . . . 1 . .
C C3 0.2662(3) 0.43413(19) 0.70481(8) 0.0178(4) Uani d . . . 1 . .
C C4 0.4745(2) 0.39817(19) 0.69254(8) 0.0175(4) Uani d . . . 1 . .
H H2 0.49692 0.300064 0.707859 0.021 Uiso calc U . R 1 . .
C C5 0.5377(2) 0.3984(2) 0.62986(8) 0.0187(4) Uani d . . . 1 . .
C C6 0.5788(2) 0.2675(2) 0.60404(8) 0.0202(4) Uani d . . . 1 . .
H H5 0.565171 0.181998 0.625635 0.024 Uiso calc U . R 1 . .
C C7 0.6398(3) 0.2623(2) 0.54652(8) 0.0253(4) Uani d . . . 1 . .
C C8 0.6827(4) 0.0111(2) 0.55147(10) 0.0367(5) Uani d . . . 1 . .
H H6 0.763638 0.021726 0.585461 0.055 Uiso calc U . R 1 . .
H H7 0.727864 -0.067806 0.527437 0.055 Uiso calc U . R 1 . .
H H1 0.55501 -0.008928 0.56422 0.055 Uiso calc U . R 1 . .
C C9 0.5793(3) 0.5005(2) 0.73229(8) 0.0224(4) Uani d . . . 1 . .
H H3 0.697658 0.457518 0.745754 0.027 Uiso calc U . R 1 . .
H H4 0.607707 0.590523 0.711768 0.027 Uiso calc U . R 1 . .
C C10 0.2763(3) 0.5067(2) 0.76459(8) 0.0221(4) Uani d . . . 1 . .
C C11 0.6596(3) 0.3873(3) 0.51477(9) 0.0301(4) Uani d . . . 1 . .
H H8 0.700977 0.383815 0.47563 0.036 Uiso calc U . R 1 . .
C C12 0.6188(3) 0.5162(2) 0.54036(9) 0.0282(4) Uani d . . . 1 . .
H H9 0.631939 0.601343 0.518509 0.034 Uiso calc U . R 1 . .
C C13 0.5585(3) 0.5235(2) 0.59794(8) 0.0221(4) Uani d . . . 1 . .
H H10 0.531932 0.613039 0.615221 0.027 Uiso calc U . R 1 . .
C C14 0.1344(3) 0.3059(2) 0.70492(8) 0.0208(4) Uani d . . . 1 . .
H H12 0.198306 0.219405 0.719267 0.025 Uiso calc U . R 1 . .
H H11 0.023205 0.324304 0.729253 0.025 Uiso calc U . R 1 . .
C C15 0.0812(3) 0.2907(2) 0.64118(9) 0.0230(4) Uani d . . . 1 . .
H H13 -0.035427 0.235413 0.63677 0.028 Uiso calc U . R 1 . .
H H14 0.181705 0.243406 0.618909 0.028 Uiso calc U . R 1 . .
C C16 0.0546(3) 0.4441(2) 0.62129(8) 0.0229(4) Uani d . . . 1 . .
H H16 0.095288 0.456452 0.580537 0.027 Uiso calc U . R 1 . .
H H15 -0.077459 0.473505 0.624765 0.027 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
F1 C1 . 1.337(3) ?
F2 C1 . 1.339(3) ?
F3 C1 . 1.320(2) ?
O1 C7 . 1.364(3) ?
O1 C8 . 1.425(3) ?
O2 C2 . 1.222(3) ?
O3 C10 . 1.348(3) ?
O3 C9 . 1.451(2) ?
O4 C10 . 1.196(3) ?
N1 C2 . 1.335(2) ?
N1 C3 . 1.478(2) ?
N1 C16 . 1.487(2) ?
C1 C2 . 1.546(3) ?
C3 C14 . 1.531(3) ?
C3 C10 . 1.539(2) ?
C3 C4 . 1.558(2) ?
C4 C5 . 1.514(2) ?
C4 C9 . 1.526(2) ?
C4 H2 . 1.0 ?
C5 C13 . 1.395(3) ?
C5 C6 . 1.398(3) ?
C6 C7 . 1.397(3) ?
C6 H5 . 0.95 ?
C7 C11 . 1.391(3) ?
C8 H6 . 0.98 ?
C8 H7 . 0.98 ?
C8 H1 . 0.98 ?
C9 H3 . 0.99 ?
C9 H4 . 0.99 ?
C11 C12 . 1.379(3) ?
C11 H8 . 0.95 ?
C12 C13 . 1.397(3) ?
C12 H9 . 0.95 ?
C13 H10 . 0.95 ?
C14 C15 . 1.524(3) ?
C14 H12 . 0.99 ?
C14 H11 . 0.99 ?
C15 C16 . 1.525(3) ?
C15 H13 . 0.99 ?
C15 H14 . 0.99 ?
C16 H16 . 0.99 ?
C16 H15 . 0.99 ?

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
C7 O1 C8 . . 117.39(16) ?
C10 O3 C9 . . 110.28(14) ?
C2 N1 C3 . . 120.48(16) ?
C2 N1 C16 . . 127.87(16) ?
C3 N1 C16 . . 111.61(14) ?
F3 C1 F1 . . 107.50(18) ?
F3 C1 F2 . . 107.95(17) ?
F1 C1 F2 . . 107.21(19) ?
F3 C1 C2 . . 110.52(17) ?
F1 C1 C2 . . 112.23(17) ?
F2 C1 C2 . . 111.23(17) ?
O2 C2 N1 . . 124.99(18) ?
O2 C2 C1 . . 118.14(17) ?
N1 C2 C1 . . 116.87(17) ?
N1 C3 C14 . . 101.11(14) ?
N1 C3 C10 . . 111.31(15) ?
C14 C3 C10 . . 112.09(15) ?
N1 C3 C4 . . 115.46(15) ?
C14 C3 C4 . . 114.94(15) ?
C10 C3 C4 . . 102.33(14) ?
C5 C4 C9 . . 115.10(15) ?
C5 C4 C3 . . 117.39(15) ?
C9 C4 C3 . . 103.10(14) ?
C5 C4 H2 . . 106.9 ?
C9 C4 H2 . . 106.9 ?
C3 C4 H2 . . 106.9 ?
C13 C5 C6 . . 119.65(17) ?
C13 C5 C4 . . 122.45(17) ?
C6 C5 C4 . . 117.89(16) ?
C7 C6 C5 . . 120.06(18) ?
C7 C6 H5 . . 120.0 ?
C5 C6 H5 . . 120.0 ?
O1 C7 C11 . . 116.22(17) ?
O1 C7 C6 . . 123.7(2) ?
C11 C7 C6 . . 120.1(2) ?
O1 C8 H6 . . 109.5 ?
O1 C8 H7 . . 109.5 ?
H6 C8 H7 . . 109.5 ?
O1 C8 H1 . . 109.5 ?
H6 C8 H1 . . 109.5 ?
H7 C8 H1 . . 109.5 ?
O3 C9 C4 . . 105.40(15) ?
O3 C9 H3 . . 110.7 ?
C4 C9 H3 . . 110.7 ?
O3 C9 H4 . . 110.7 ?
C4 C9 H4 . . 110.7 ?
H3 C9 H4 . . 108.8 ?
O4 C10 O3 . . 122.73(17) ?
O4 C10 C3 . . 126.39(19) ?
O3 C10 C3 . . 110.75(16) ?
C12 C11 C7 . . 119.69(18) ?
C12 C11 H8 . . 120.2 ?
C7 C11 H8 . . 120.2 ?
C11 C12 C13 . . 121.00(19) ?
C11 C12 H9 . . 119.5 ?
C13 C12 H9 . . 119.5 ?
C5 C13 C12 . . 119.50(19) ?
C5 C13 H10 . . 120.2 ?
C12 C13 H10 . . 120.2 ?
C15 C14 C3 . . 103.10(14) ?
C15 C14 H12 . . 111.1 ?
C3 C14 H12 . . 111.1 ?
C15 C14 H11 . . 111.1 ?
C3 C14 H11 . . 111.1 ?
H12 C14 H11 . . 109.1 ?
C14 C15 C16 . . 103.44(15) ?
C14 C15 H13 . . 111.1 ?
C16 C15 H13 . . 111.1 ?
C14 C15 H14 . . 111.1 ?
C16 C15 H14 . . 111.1 ?
H13 C15 H14 . . 109.0 ?
N1 C16 C15 . . 103.60(14) ?
N1 C16 H16 . . 111.0 ?
C15 C16 H16 . . 111.0 ?
N1 C16 H15 . . 111.0 ?
C15 C16 H15 . . 111.0 ?
H16 C16 H15 . . 109.0 ?

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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C3 N1 C2 O2 . . . . 4.0(3) ?
C16 N1 C2 O2 . . . . -178.51(19) ?
C3 N1 C2 C1 . . . . -175.17(16) ?
C16 N1 C2 C1 . . . . 2.3(3) ?
F3 C1 C2 O2 . . . . 5.7(3) ?
F1 C1 C2 O2 . . . . 125.7(2) ?
F2 C1 C2 O2 . . . . -114.2(2) ?
F3 C1 C2 N1 . . . . -175.03(17) ?
F1 C1 C2 N1 . . . . -55.0(3) ?
F2 C1 C2 N1 . . . . 65.1(2) ?
C2 N1 C3 C14 . . . . 154.96(16) ?
C16 N1 C3 C14 . . . . -22.90(18) ?
C2 N1 C3 C10 . . . . 35.7(2) ?
C16 N1 C3 C10 . . . . -142.11(16) ?
C2 N1 C3 C4 . . . . -80.3(2) ?
C16 N1 C3 C4 . . . . 101.81(17) ?
N1 C3 C4 C5 . . . . -27.6(2) ?
C14 C3 C4 C5 . . . . 89.5(2) ?
C10 C3 C4 C5 . . . . -148.70(16) ?
N1 C3 C4 C9 . . . . 100.04(17) ?
C14 C3 C4 C9 . . . . -142.78(15) ?
C10 C3 C4 C9 . . . . -21.03(17) ?
C9 C4 C5 C13 . . . . -49.6(2) ?
C3 C4 C5 C13 . . . . 72.0(2) ?
C9 C4 C5 C6 . . . . 129.40(18) ?
C3 C4 C5 C6 . . . . -108.96(18) ?
C13 C5 C6 C7 . . . . -0.2(3) ?
C4 C5 C6 C7 . . . . -179.23(16) ?
C8 O1 C7 C11 . . . . 174.36(19) ?
C8 O1 C7 C6 . . . . -4.9(3) ?
C5 C6 C7 O1 . . . . 179.08(17) ?
C5 C6 C7 C11 . . . . -0.1(3) ?
C10 O3 C9 C4 . . . . -25.96(19) ?
C5 C4 C9 O3 . . . . 157.58(15) ?
C3 C4 C9 O3 . . . . 28.48(17) ?
C9 O3 C10 O4 . . . . -172.07(18) ?
C9 O3 C10 C3 . . . . 11.9(2) ?
N1 C3 C10 O4 . . . . 66.9(2) ?
C14 C3 C10 O4 . . . . -45.5(3) ?
C4 C3 C10 O4 . . . . -169.20(19) ?
N1 C3 C10 O3 . . . . -117.26(17) ?
C14 C3 C10 O3 . . . . 130.30(16) ?
C4 C3 C10 O3 . . . . 6.62(19) ?
O1 C7 C11 C12 . . . . -179.19(19) ?
C6 C7 C11 C12 . . . . 0.1(3) ?
C7 C11 C12 C13 . . . . 0.3(3) ?
C6 C5 C13 C12 . . . . 0.5(3) ?
C4 C5 C13 C12 . . . . 179.51(17) ?
C11 C12 C13 C5 . . . . -0.6(3) ?
N1 C3 C14 C15 . . . . 38.36(17) ?
C10 C3 C14 C15 . . . . 157.01(15) ?
C4 C3 C14 C15 . . . . -86.70(18) ?
C3 C14 C15 C16 . . . . -40.55(18) ?
C2 N1 C16 C15 . . . . -179.39(18) ?
C3 N1 C16 C15 . . . . -1.7(2) ?
C14 C15 C16 N1 . . . . 25.99(19) ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
C4 H2 O3 3_646 1.00 2.61 3.584(2) 164.9 ?
C6 H5 O3 3_646 0.95 2.61 3.497(2) 155.9 ?
C9 H3 O2 3_646 0.99 2.52 3.139(2) 120.4 ?
C15 H13 O4 3_546 0.99 2.57 3.251(2) 125.7 ?
C16 H16 O1 2_456 0.99 2.53 3.443(2) 152.5 ?

