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

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

data_1
_database_code_depnum_ccdc_archive 'CCDC 2236216'
loop_
_audit_author_name
_audit_author_address
'Dong Qiu'
;University of Chinese Academy of Sciences
China
;
_audit_update_record             
;
2023-01-14 deposited with the CCDC.	2023-02-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H21 N O6'
_chemical_formula_weight         419.42

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/n

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

_cell_length_a                   9.4202(7)
_cell_length_b                   18.5520(13)
_cell_length_c                   12.6365(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 110.2940(10)
_cell_angle_gamma                90.00
_cell_volume                     2071.3(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4335
_cell_measurement_theta_min      2.20
_cell_measurement_theta_max      27.90

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.345
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             880
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.9714
_exptl_absorpt_correction_T_max  0.9808
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX II area detector'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10414
_diffrn_reflns_av_R_equivalents  0.0200
_diffrn_reflns_av_sigmaI/netI    0.0228
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.04
_diffrn_reflns_theta_max         25.00
_reflns_number_total             3642
_reflns_number_gt                2992
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART APEX II'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SMART'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0200P)²+0.8322P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0239(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3642
_refine_ls_number_parameters     283
_refine_ls_number_restraints     13
_refine_ls_R_factor_all          0.0460
_refine_ls_R_factor_gt           0.0371
_refine_ls_wR_factor_ref         0.0822
_refine_ls_wR_factor_gt          0.0773
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_restrained_S_all      1.026
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.20089(18) 0.21597(9) -0.05617(14) 0.0467(4) Uani 1 1 d . . .
C2 C 0.1409(2) 0.21971(10) -0.17297(15) 0.0581(5) Uani 1 1 d . . .
H2 H 0.0601 0.1902 -0.2125 0.070 Uiso 1 1 calc R . .
C3 C 0.2007(3) 0.26695(12) -0.23067(18) 0.0729(6) Uani 1 1 d . . .
H3 H 0.1593 0.2695 -0.3089 0.087 Uiso 1 1 calc R . .
C4 C 0.3199(3) 0.30985(12) -0.1738(2) 0.0794(7) Uani 1 1 d . . .
H4 H 0.3610 0.3409 -0.2133 0.095 Uiso 1 1 calc R . .
C5 C 0.3793(3) 0.30734(12) -0.0586(2) 0.0810(7) Uani 1 1 d . . .
H5 H 0.4600 0.3371 -0.0200 0.097 Uiso 1 1 calc R . .
C6 C 0.3202(2) 0.26084(10) 0.00064(17) 0.0651(5) Uani 1 1 d . . .
H6 H 0.3607 0.2597 0.0790 0.078 Uiso 1 1 calc R . .
C7 C 0.13621(18) 0.16257(9) 0.00185(14) 0.0470(4) Uani 1 1 d . . .
C8 C 0.19977(18) 0.15520(9) 0.13001(14) 0.0465(4) Uani 1 1 d . . .
C9 C 0.20935(17) 0.08059(8) 0.17796(13) 0.0423(4) Uani 1 1 d . . .
H9A H 0.1777 0.0462 0.1164 0.051 Uiso 1 1 calc R . .
H9B H 0.1395 0.0769 0.2189 0.051 Uiso 1 1 calc R . .
C10 C 0.37030(16) 0.06029(8) 0.25828(12) 0.0365(3) Uani 1 1 d . . .
C11 C 0.47728(17) 0.05949(8) 0.19003(12) 0.0366(3) Uani 1 1 d . . .
C13 C 0.5113(2) 0.09682(9) 0.02613(14) 0.0520(4) Uani 1 1 d U . .
H13 H 0.4731 0.1211 -0.0423 0.062 Uiso 1 1 calc R . .
C14 C 0.6495(2) 0.06721(9) 0.05504(14) 0.0524(4) Uani 1 1 d U . .
H14 H 0.7038 0.0701 0.0062 0.063 Uiso 1 1 calc R . .
C15 C 0.71213(18) 0.03172(9) 0.15967(14) 0.0468(4) Uani 1 1 d . . .
C16 C 0.8582(2) 0.00105(10) 0.19688(19) 0.0623(5) Uani 1 1 d . . .
H16 H 0.9143 0.0011 0.1491 0.075 Uiso 1 1 calc R . .
C17 C 0.9179(2) -0.02840(11) 0.3005(2) 0.0703(6) Uani 1 1 d . . .
H17 H 1.0156 -0.0471 0.3243 0.084 Uiso 1 1 calc R . .
C18 C 0.8337(2) -0.03105(10) 0.37250(17) 0.0612(5) Uani 1 1 d . . .
H18 H 0.8760 -0.0512 0.4440 0.073 Uiso 1 1 calc R . .
C19 C 0.69043(18) -0.00433(9) 0.33864(14) 0.0480(4) Uani 1 1 d . . .
H19 H 0.6348 -0.0075 0.3866 0.058 Uiso 1 1 calc R . .
C20 C 0.62479(17) 0.02832(8) 0.23137(13) 0.0398(4) Uani 1 1 d . . .
C21 C 0.35321(16) -0.01477(9) 0.30213(13) 0.0414(4) Uani 1 1 d . . .
C22 C 0.3125(2) -0.13751(10) 0.25136(18) 0.0733(6) Uani 1 1 d . . .
H22A H 0.3958 -0.1509 0.3175 0.110 Uiso 1 1 calc R . .
H22B H 0.3091 -0.1689 0.1901 0.110 Uiso 1 1 calc R . .
H22C H 0.2197 -0.1416 0.2663 0.110 Uiso 1 1 calc R . .
C23 C 0.43517(17) 0.11335(9) 0.35732(13) 0.0417(4) Uani 1 1 d . . .
H23A H 0.5196 0.0898 0.4140 0.050 Uiso 1 1 calc R . .
H23B H 0.4757 0.1544 0.3298 0.050 Uiso 1 1 calc R . .
C24 C 0.33140(19) 0.14139(9) 0.41455(13) 0.0464(4) Uani 1 1 d . . .
C25 C 0.3160(3) 0.22855(15) 0.5449(2) 0.1000(9) Uani 1 1 d . . .
H25A H 0.2221 0.2477 0.4947 0.150 Uiso 1 1 calc R . .
H25B H 0.3749 0.2667 0.5908 0.150 Uiso 1 1 calc R . .
H25C H 0.2959 0.1925 0.5923 0.150 Uiso 1 1 calc R . .
N1 N 0.42427(15) 0.09284(7) 0.09261(10) 0.0437(3) Uani 1 1 d . . .
O1 O 0.02931(14) 0.12463(7) -0.04810(11) 0.0673(4) Uani 1 1 d . . .
O2 O 0.22520(17) 0.20881(7) 0.18827(11) 0.0702(4) Uani 1 1 d . . .
O3 O 0.33204(14) -0.06387(6) 0.22135(10) 0.0571(3) Uani 1 1 d . . .
O4 O 0.35354(15) -0.02796(7) 0.39464(10) 0.0625(4) Uani 1 1 d . . .
O5 O 0.20906(14) 0.11973(7) 0.40758(11) 0.0656(4) Uani 1 1 d . . .
O6 O 0.39901(15) 0.19666(8) 0.47996(12) 0.0722(4) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C6 1.383(2) . ?
C1 C2 1.387(2) . ?
C1 C7 1.483(2) . ?
C2 C3 1.379(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.361(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.367(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.380(3) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 O1 1.2112(19) . ?
C7 C8 1.526(2) . ?
C8 O2 1.2110(19) . ?
C8 C9 1.501(2) . ?
C9 C10 1.550(2) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C21 1.528(2) . ?
C10 C11 1.537(2) . ?
C10 C23 1.542(2) . ?
C11 N1 1.3119(19) . ?
C11 C20 1.426(2) . ?
C13 C14 1.342(2) . ?
C13 N1 1.364(2) . ?
C13 H13 0.9300 . ?
C14 C15 1.410(2) . ?
C14 H14 0.9300 . ?
C15 C16 1.411(2) . ?
C15 C20 1.421(2) . ?
C16 C17 1.349(3) . ?
C16 H16 0.9300 . ?
C17 C18 1.400(3) . ?
C17 H17 0.9300 . ?
C18 C19 1.360(2) . ?
C18 H18 0.9300 . ?
C19 C20 1.416(2) . ?
C19 H19 0.9300 . ?
C21 O4 1.1933(18) . ?
C21 O3 1.3306(19) . ?
C22 O3 1.446(2) . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 C24 1.497(2) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C24 O5 1.1945(19) . ?
C24 O6 1.332(2) . ?
C25 O6 1.442(2) . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 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
C6 C1 C2 118.68(17) . . ?
C6 C1 C7 123.01(16) . . ?
C2 C1 C7 118.29(16) . . ?
C3 C2 C1 120.3(2) . . ?
C3 C2 H2 119.9 . . ?
C1 C2 H2 119.9 . . ?
C4 C3 C2 120.4(2) . . ?
C4 C3 H3 119.8 . . ?
C2 C3 H3 119.8 . . ?
C3 C4 C5 120.1(2) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
C4 C5 C6 120.4(2) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 H5 119.8 . . ?
C5 C6 C1 120.2(2) . . ?
C5 C6 H6 119.9 . . ?
C1 C6 H6 119.9 . . ?
O1 C7 C1 122.71(15) . . ?
O1 C7 C8 116.76(16) . . ?
C1 C7 C8 120.49(14) . . ?
O2 C8 C9 122.71(15) . . ?
O2 C8 C7 119.59(15) . . ?
C9 C8 C7 117.24(14) . . ?
C8 C9 C10 113.35(13) . . ?
C8 C9 H9A 108.9 . . ?
C10 C9 H9A 108.9 . . ?
C8 C9 H9B 108.9 . . ?
C10 C9 H9B 108.9 . . ?
H9A C9 H9B 107.7 . . ?
C21 C10 C11 111.51(12) . . ?
C21 C10 C23 110.45(12) . . ?
C11 C10 C23 108.01(11) . . ?
C21 C10 C9 104.87(12) . . ?
C11 C10 C9 108.52(12) . . ?
C23 C10 C9 113.49(12) . . ?
N1 C11 C20 122.70(13) . . ?
N1 C11 C10 114.31(13) . . ?
C20 C11 C10 122.92(13) . . ?
C14 C13 N1 122.94(16) . . ?
C14 C13 H13 118.5 . . ?
N1 C13 H13 118.5 . . ?
C13 C14 C15 119.84(15) . . ?
C13 C14 H14 120.1 . . ?
C15 C14 H14 120.1 . . ?
C14 C15 C16 122.92(16) . . ?
C14 C15 C20 118.17(15) . . ?
C16 C15 C20 118.90(17) . . ?
C17 C16 C15 121.15(17) . . ?
C17 C16 H16 119.4 . . ?
C15 C16 H16 119.4 . . ?
C16 C17 C18 120.37(18) . . ?
C16 C17 H17 119.8 . . ?
C18 C17 H17 119.8 . . ?
C19 C18 C17 120.46(19) . . ?
C19 C18 H18 119.8 . . ?
C17 C18 H18 119.8 . . ?
C18 C19 C20 120.88(16) . . ?
C18 C19 H19 119.6 . . ?
C20 C19 H19 119.6 . . ?
C19 C20 C15 118.18(14) . . ?
C19 C20 C11 124.78(14) . . ?
C15 C20 C11 117.03(14) . . ?
O4 C21 O3 124.05(15) . . ?
O4 C21 C10 125.27(15) . . ?
O3 C21 C10 110.64(12) . . ?
O3 C22 H22A 109.5 . . ?
O3 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
O3 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C24 C23 C10 118.21(13) . . ?
C24 C23 H23A 107.8 . . ?
C10 C23 H23A 107.8 . . ?
C24 C23 H23B 107.8 . . ?
C10 C23 H23B 107.8 . . ?
H23A C23 H23B 107.1 . . ?
O5 C24 O6 123.10(15) . . ?
O5 C24 C23 128.51(16) . . ?
O6 C24 C23 108.39(14) . . ?
O6 C25 H25A 109.5 . . ?
O6 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
O6 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C11 N1 C13 119.26(14) . . ?
C21 O3 C22 116.38(14) . . ?
C24 O6 C25 115.59(15) . . ?

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 C1 C2 C3 0.6(3) . . . . ?
C7 C1 C2 C3 -177.95(16) . . . . ?
C1 C2 C3 C4 0.6(3) . . . . ?
C2 C3 C4 C5 -1.3(3) . . . . ?
C3 C4 C5 C6 0.7(3) . . . . ?
C4 C5 C6 C1 0.5(3) . . . . ?
C2 C1 C6 C5 -1.1(3) . . . . ?
C7 C1 C6 C5 177.34(18) . . . . ?
C6 C1 C7 O1 178.15(18) . . . . ?
C2 C1 C7 O1 -3.4(2) . . . . ?
C6 C1 C7 C8 0.4(2) . . . . ?
C2 C1 C7 C8 178.88(15) . . . . ?
O1 C7 C8 O2 -132.56(19) . . . . ?
C1 C7 C8 O2 45.3(2) . . . . ?
O1 C7 C8 C9 39.9(2) . . . . ?
C1 C7 C8 C9 -142.24(15) . . . . ?
O2 C8 C9 C10 -62.6(2) . . . . ?
C7 C8 C9 C10 125.15(15) . . . . ?
C8 C9 C10 C21 176.91(13) . . . . ?
C8 C9 C10 C11 -63.81(16) . . . . ?
C8 C9 C10 C23 56.27(17) . . . . ?
C21 C10 C11 N1 131.84(13) . . . . ?
C23 C10 C11 N1 -106.62(14) . . . . ?
C9 C10 C11 N1 16.81(17) . . . . ?
C21 C10 C11 C20 -51.15(18) . . . . ?
C23 C10 C11 C20 70.39(17) . . . . ?
C9 C10 C11 C20 -166.18(13) . . . . ?
N1 C13 C14 C15 -1.8(3) . . . . ?
C13 C14 C15 C16 -178.27(16) . . . . ?
C13 C14 C15 C20 0.3(2) . . . . ?
C14 C15 C16 C17 175.72(17) . . . . ?
C20 C15 C16 C17 -2.9(3) . . . . ?
C15 C16 C17 C18 1.9(3) . . . . ?
C16 C17 C18 C19 0.3(3) . . . . ?
C17 C18 C19 C20 -1.6(3) . . . . ?
C18 C19 C20 C15 0.6(2) . . . . ?
C18 C19 C20 C11 -178.21(16) . . . . ?
C14 C15 C20 C19 -177.09(14) . . . . ?
C16 C15 C20 C19 1.6(2) . . . . ?
C14 C15 C20 C11 1.8(2) . . . . ?
C16 C15 C20 C11 -179.51(14) . . . . ?
N1 C11 C20 C19 176.00(15) . . . . ?
C10 C11 C20 C19 -0.8(2) . . . . ?
N1 C11 C20 C15 -2.9(2) . . . . ?
C10 C11 C20 C15 -179.62(13) . . . . ?
C11 C10 C21 O4 137.11(16) . . . . ?
C23 C10 C21 O4 17.0(2) . . . . ?
C9 C10 C21 O4 -105.63(18) . . . . ?
C11 C10 C21 O3 -45.21(17) . . . . ?
C23 C10 C21 O3 -165.32(12) . . . . ?
C9 C10 C21 O3 72.05(15) . . . . ?
C21 C10 C23 C24 -76.53(17) . . . . ?
C11 C10 C23 C24 161.27(13) . . . . ?
C9 C10 C23 C24 40.90(19) . . . . ?
C10 C23 C24 O5 13.9(3) . . . . ?
C10 C23 C24 O6 -167.13(14) . . . . ?
C20 C11 N1 C13 1.6(2) . . . . ?
C10 C11 N1 C13 178.57(13) . . . . ?
C14 C13 N1 C11 0.8(2) . . . . ?
O4 C21 O3 C22 -1.7(2) . . . . ?
C10 C21 O3 C22 -179.38(14) . . . . ?
O5 C24 O6 C25 1.2(3) . . . . ?
C23 C24 O6 C25 -177.83(18) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.176
_refine_diff_density_min         -0.178
_refine_diff_density_rms         0.032
####################################################################### 
# 
# 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_1_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2236219'
loop_
_audit_author_name
_audit_author_address
'Dong Qiu'
;University of Chinese Academy of Sciences
China
;
_audit_update_record             
;
2023-01-14 deposited with the CCDC.	2023-02-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H23 N O5'
_chemical_formula_weight         405.43

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   Pna2(1)

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

_cell_length_a                   7.713(2)
_cell_length_b                   13.434(4)
_cell_length_c                   19.831(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2054.8(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3303
_cell_measurement_theta_min      3.05
_cell_measurement_theta_max      22.43

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.311
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             856
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.9729
_exptl_absorpt_correction_T_max  0.9818
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX II area detector'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10225
_diffrn_reflns_av_R_equivalents  0.0306
_diffrn_reflns_av_sigmaI/netI    0.0347
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         1.83
_diffrn_reflns_theta_max         25.58
_reflns_number_total             3690
_reflns_number_gt                3116
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART APEX II'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SMART'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0800P)²+0.2936P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.6(13)
_refine_ls_number_reflns         3690
_refine_ls_number_parameters     273
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0504
_refine_ls_R_factor_gt           0.0383
_refine_ls_wR_factor_ref         0.1291
_refine_ls_wR_factor_gt          0.1087
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_restrained_S_all      1.001
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.2674(3) 0.7857(2) 0.36725(14) 0.0460(6) Uani 1 1 d . . .
C2 C 0.3097(4) 0.8732(2) 0.40175(18) 0.0647(9) Uani 1 1 d . . .
H2 H 0.3010 0.9344 0.3801 0.078 Uiso 1 1 calc R . .
C3 C 0.3646(6) 0.8689(3) 0.4684(2) 0.0827(12) Uani 1 1 d . . .
H3 H 0.3871 0.9274 0.4918 0.099 Uiso 1 1 calc R . .
C4 C 0.3858(5) 0.7785(3) 0.49982(18) 0.0774(11) Uani 1 1 d . . .
H4 H 0.4263 0.7761 0.5440 0.093 Uiso 1 1 calc R . .
C5 C 0.3475(5) 0.6920(3) 0.46647(17) 0.0706(10) Uani 1 1 d . . .
H5 H 0.3634 0.6310 0.4877 0.085 Uiso 1 1 calc R . .
C6 C 0.2849(4) 0.6957(2) 0.40109(16) 0.0579(7) Uani 1 1 d . . .
H6 H 0.2540 0.6369 0.3794 0.069 Uiso 1 1 calc R . .
C7 C 0.2051(3) 0.78536(19) 0.29627(13) 0.0431(6) Uani 1 1 d . . .
C8 C 0.2237(4) 0.88044(19) 0.25448(12) 0.0405(6) Uani 1 1 d . . .
H8 H 0.3363 0.9116 0.2632 0.049 Uiso 1 1 calc R . .
C9 C 0.0739(3) 0.95425(17) 0.27232(13) 0.0405(5) Uani 1 1 d . . .
H9A H -0.0067 0.9235 0.3036 0.049 Uiso 1 1 calc R . .
H9B H 0.1203 1.0140 0.2930 0.049 Uiso 1 1 calc R . .
C10 C -0.0184(3) 0.97999(17) 0.20554(11) 0.0357(5) Uani 1 1 d . . .
C11 C 0.0236(3) 0.88115(17) 0.16424(12) 0.0371(5) Uani 1 1 d . . .
H11 H -0.0470 0.8279 0.1839 0.045 Uiso 1 1 calc R . .
C12 C -0.0087(4) 0.87956(19) 0.08871(13) 0.0432(6) Uani 1 1 d . . .
C13 C -0.1691(4) 0.8573(2) 0.06324(15) 0.0551(7) Uani 1 1 d . . .
H13 H -0.2593 0.8428 0.0927 0.066 Uiso 1 1 calc R . .
C14 C -0.1997(6) 0.8558(3) -0.00586(18) 0.0725(10) Uani 1 1 d . . .
H14 H -0.3098 0.8408 -0.0221 0.087 Uiso 1 1 calc R . .
C15 C -0.0689(6) 0.8763(3) -0.04978(17) 0.0775(11) Uani 1 1 d . . .
H15 H -0.0896 0.8760 -0.0960 0.093 Uiso 1 1 calc R . .
C16 C 0.0970(5) 0.8979(3) -0.02504(16) 0.0671(9) Uani 1 1 d . . .
H16 H 0.1861 0.9124 -0.0551 0.081 Uiso 1 1 calc R . .
C17 C 0.1304(4) 0.8980(2) 0.04444(14) 0.0519(7) Uani 1 1 d . . .
C18 C 0.3040(4) 0.9108(3) 0.07304(17) 0.0607(8) Uani 1 1 d . . .
H18 H 0.3940 0.9333 0.0458 0.073 Uiso 1 1 calc R . .
C19 C 0.3343(4) 0.8906(2) 0.13791(15) 0.0515(7) Uani 1 1 d . . .
H19 H 0.4468 0.8969 0.1542 0.062 Uiso 1 1 calc R . .
C20 C -0.2128(3) 0.99559(18) 0.21275(14) 0.0410(5) Uani 1 1 d . . .
H20A H -0.2605 1.0136 0.1692 0.049 Uiso 1 1 calc R . .
H20B H -0.2660 0.9333 0.2264 0.049 Uiso 1 1 calc R . .
C21 C -0.2594(4) 1.07487(19) 0.26306(15) 0.0446(6) Uani 1 1 d . . .
C22 C 0.0612(3) 1.06989(17) 0.16965(13) 0.0394(5) Uani 1 1 d . . .
C23 C 0.3096(5) 1.1699(3) 0.15673(19) 0.0732(10) Uani 1 1 d . . .
H23A H 0.3312 1.1487 0.1113 0.110 Uiso 1 1 calc R . .
H23B H 0.4179 1.1833 0.1788 0.110 Uiso 1 1 calc R . .
H23C H 0.2403 1.2293 0.1562 0.110 Uiso 1 1 calc R . .
C24 C -0.4904(6) 1.1452(3) 0.3262(2) 0.0879(13) Uani 1 1 d . . .
H24A H -0.5348 1.1132 0.3659 0.132 Uiso 1 1 calc R . .
H24B H -0.5816 1.1821 0.3047 0.132 Uiso 1 1 calc R . .
H24C H -0.3983 1.1896 0.3385 0.132 Uiso 1 1 calc R . .
N1 N 0.2038(3) 0.86032(15) 0.18224(10) 0.0396(5) Uani 1 1 d . . .
O1 O -0.0110(3) 1.11519(14) 0.12513(11) 0.0561(5) Uani 1 1 d . . .
O2 O -0.4248(3) 1.07034(16) 0.27986(13) 0.0668(6) Uani 1 1 d . . .
O3 O -0.1618(3) 1.13542(17) 0.28596(15) 0.0754(7) Uani 1 1 d . . .
O4 O 0.2185(3) 1.09227(14) 0.19271(11) 0.0517(5) Uani 1 1 d . . .
O5 O 0.1403(3) 0.71144(14) 0.27159(11) 0.0589(5) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C6 1.390(4) . ?
C1 C2 1.398(5) . ?
C1 C7 1.487(4) . ?
C2 C3 1.389(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.374(6) . ?
C3 H3 0.9300 . ?
C4 C5 1.369(6) . ?
C4 H4 0.9300 . ?
C5 C6 1.385(5) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 O5 1.215(3) . ?
C7 C8 1.529(4) . ?
C8 N1 1.466(3) . ?
C8 C9 1.563(4) . ?
C8 H8 0.9800 . ?
C9 C10 1.543(3) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C20 1.521(3) . ?
C10 C22 1.531(3) . ?
C10 C11 1.593(3) . ?
C11 N1 1.462(3) . ?
C11 C12 1.519(3) . ?
C11 H11 0.9800 . ?
C12 C13 1.370(4) . ?
C12 C17 1.408(4) . ?
C13 C14 1.391(5) . ?
C13 H13 0.9300 . ?
C14 C15 1.361(6) . ?
C14 H14 0.9300 . ?
C15 C16 1.401(6) . ?
C15 H15 0.9300 . ?
C16 C17 1.402(4) . ?
C16 H16 0.9300 . ?
C17 C18 1.465(5) . ?
C18 C19 1.335(5) . ?
C18 H18 0.9300 . ?
C19 N1 1.397(3) . ?
C19 H19 0.9300 . ?
C20 C21 1.503(4) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C21 O3 1.198(4) . ?
C21 O2 1.320(3) . ?
C22 O1 1.208(3) . ?
C22 O4 1.331(3) . ?
C23 O4 1.446(4) . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C24 O2 1.452(4) . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 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
C6 C1 C2 118.2(3) . . ?
C6 C1 C7 119.0(3) . . ?
C2 C1 C7 122.8(3) . . ?
C3 C2 C1 120.1(3) . . ?
C3 C2 H2 120.0 . . ?
C1 C2 H2 120.0 . . ?
C4 C3 C2 120.3(4) . . ?
C4 C3 H3 119.8 . . ?
C2 C3 H3 119.8 . . ?
C5 C4 C3 120.3(3) . . ?
C5 C4 H4 119.8 . . ?
C3 C4 H4 119.8 . . ?
C4 C5 C6 119.8(3) . . ?
C4 C5 H5 120.1 . . ?
C6 C5 H5 120.1 . . ?
C5 C6 C1 121.1(3) . . ?
C5 C6 H6 119.4 . . ?
C1 C6 H6 119.4 . . ?
O5 C7 C1 121.1(2) . . ?
O5 C7 C8 120.2(2) . . ?
C1 C7 C8 118.7(2) . . ?
N1 C8 C7 111.5(2) . . ?
N1 C8 C9 105.1(2) . . ?
C7 C8 C9 109.8(2) . . ?
N1 C8 H8 110.1 . . ?
C7 C8 H8 110.1 . . ?
C9 C8 H8 110.1 . . ?
C10 C9 C8 106.80(19) . . ?
C10 C9 H9A 110.4 . . ?
C8 C9 H9A 110.4 . . ?
C10 C9 H9B 110.4 . . ?
C8 C9 H9B 110.4 . . ?
H9A C9 H9B 108.6 . . ?
C20 C10 C22 109.32(19) . . ?
C20 C10 C9 113.9(2) . . ?
C22 C10 C9 113.0(2) . . ?
C20 C10 C11 111.33(18) . . ?
C22 C10 C11 109.68(18) . . ?
C9 C10 C11 99.24(18) . . ?
N1 C11 C12 113.2(2) . . ?
N1 C11 C10 103.15(18) . . ?
C12 C11 C10 119.0(2) . . ?
N1 C11 H11 106.9 . . ?
C12 C11 H11 106.9 . . ?
C10 C11 H11 106.9 . . ?
C13 C12 C17 119.8(3) . . ?
C13 C12 C11 121.0(3) . . ?
C17 C12 C11 119.2(2) . . ?
C12 C13 C14 121.3(3) . . ?
C12 C13 H13 119.3 . . ?
C14 C13 H13 119.3 . . ?
C15 C14 C13 120.1(4) . . ?
C15 C14 H14 119.9 . . ?
C13 C14 H14 119.9 . . ?
C14 C15 C16 119.7(3) . . ?
C14 C15 H15 120.2 . . ?
C16 C15 H15 120.2 . . ?
C15 C16 C17 120.8(3) . . ?
C15 C16 H16 119.6 . . ?
C17 C16 H16 119.6 . . ?
C16 C17 C12 118.2(3) . . ?
C16 C17 C18 123.3(3) . . ?
C12 C17 C18 118.4(3) . . ?
C19 C18 C17 120.6(3) . . ?
C19 C18 H18 119.7 . . ?
C17 C18 H18 119.7 . . ?
C18 C19 N1 122.7(3) . . ?
C18 C19 H19 118.7 . . ?
N1 C19 H19 118.7 . . ?
C21 C20 C10 113.3(2) . . ?
C21 C20 H20A 108.9 . . ?
C10 C20 H20A 108.9 . . ?
C21 C20 H20B 108.9 . . ?
C10 C20 H20B 108.9 . . ?
H20A C20 H20B 107.7 . . ?
O3 C21 O2 122.9(3) . . ?
O3 C21 C20 125.6(3) . . ?
O2 C21 C20 111.4(2) . . ?
O1 C22 O4 123.9(2) . . ?
O1 C22 C10 123.5(2) . . ?
O4 C22 C10 112.6(2) . . ?
O4 C23 H23A 109.5 . . ?
O4 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
O4 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
O2 C24 H24A 109.5 . . ?
O2 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
O2 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C19 N1 C11 118.4(2) . . ?
C19 N1 C8 119.1(2) . . ?
C11 N1 C8 107.62(19) . . ?
C21 O2 C24 117.7(3) . . ?
C22 O4 C23 115.9(2) . . ?

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 C1 C2 C3 -1.1(5) . . . . ?
C7 C1 C2 C3 179.0(3) . . . . ?
C1 C2 C3 C4 3.2(6) . . . . ?
C2 C3 C4 C5 -2.2(6) . . . . ?
C3 C4 C5 C6 -0.9(6) . . . . ?
C4 C5 C6 C1 3.0(5) . . . . ?
C2 C1 C6 C5 -1.9(4) . . . . ?
C7 C1 C6 C5 178.0(3) . . . . ?
C6 C1 C7 O5 13.4(4) . . . . ?
C2 C1 C7 O5 -166.7(3) . . . . ?
C6 C1 C7 C8 -166.7(3) . . . . ?
C2 C1 C7 C8 13.2(4) . . . . ?
O5 C7 C8 N1 -16.4(4) . . . . ?
C1 C7 C8 N1 163.7(2) . . . . ?
O5 C7 C8 C9 99.6(3) . . . . ?
C1 C7 C8 C9 -80.2(3) . . . . ?
N1 C8 C9 C10 -4.6(3) . . . . ?
C7 C8 C9 C10 -124.6(2) . . . . ?
C8 C9 C10 C20 145.4(2) . . . . ?
C8 C9 C10 C22 -89.1(2) . . . . ?
C8 C9 C10 C11 27.0(2) . . . . ?
C20 C10 C11 N1 -161.1(2) . . . . ?
C22 C10 C11 N1 77.8(2) . . . . ?
C9 C10 C11 N1 -40.8(2) . . . . ?
C20 C10 C11 C12 72.6(3) . . . . ?
C22 C10 C11 C12 -48.5(3) . . . . ?
C9 C10 C11 C12 -167.1(2) . . . . ?
N1 C11 C12 C13 153.4(2) . . . . ?
C10 C11 C12 C13 -85.2(3) . . . . ?
N1 C11 C12 C17 -24.5(3) . . . . ?
C10 C11 C12 C17 96.9(3) . . . . ?
C17 C12 C13 C14 -2.3(4) . . . . ?
C11 C12 C13 C14 179.9(3) . . . . ?
C12 C13 C14 C15 0.3(5) . . . . ?
C13 C14 C15 C16 0.6(6) . . . . ?
C14 C15 C16 C17 0.4(5) . . . . ?
C15 C16 C17 C12 -2.4(5) . . . . ?
C15 C16 C17 C18 174.2(3) . . . . ?
C13 C12 C17 C16 3.3(4) . . . . ?
C11 C12 C17 C16 -178.9(3) . . . . ?
C13 C12 C17 C18 -173.4(3) . . . . ?
C11 C12 C17 C18 4.4(4) . . . . ?
C16 C17 C18 C19 -166.4(3) . . . . ?
C12 C17 C18 C19 10.1(5) . . . . ?
C17 C18 C19 N1 -2.5(5) . . . . ?
C22 C10 C20 C21 -70.8(3) . . . . ?
C9 C10 C20 C21 56.7(3) . . . . ?
C11 C10 C20 C21 167.9(2) . . . . ?
C10 C20 C21 O3 14.9(4) . . . . ?
C10 C20 C21 O2 -165.0(2) . . . . ?
C20 C10 C22 O1 -35.8(3) . . . . ?
C9 C10 C22 O1 -163.8(2) . . . . ?
C11 C10 C22 O1 86.5(3) . . . . ?
C20 C10 C22 O4 144.4(2) . . . . ?
C9 C10 C22 O4 16.4(3) . . . . ?
C11 C10 C22 O4 -93.3(2) . . . . ?
C18 C19 N1 C11 -19.8(4) . . . . ?
C18 C19 N1 C8 -153.7(3) . . . . ?
C12 C11 N1 C19 32.0(3) . . . . ?
C10 C11 N1 C19 -98.0(2) . . . . ?
C12 C11 N1 C8 170.7(2) . . . . ?
C10 C11 N1 C8 40.7(2) . . . . ?
C7 C8 N1 C19 -125.6(2) . . . . ?
C9 C8 N1 C19 115.5(3) . . . . ?
C7 C8 N1 C11 96.0(2) . . . . ?
C9 C8 N1 C11 -22.9(2) . . . . ?
O3 C21 O2 C24 2.5(5) . . . . ?
C20 C21 O2 C24 -177.5(3) . . . . ?
O1 C22 O4 C23 -5.8(4) . . . . ?
C10 C22 O4 C23 173.9(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.58
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.195
_refine_diff_density_min         -0.212
_refine_diff_density_rms         0.068
