# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2022

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

data_exp_12188
_database_code_depnum_ccdc_archive 'CCDC 2150432'
loop_
_audit_author_name
_audit_author_address
'xuanxuan du'
;ocean university of China
China
;
_audit_update_record             
;
2022-02-07 deposited with the CCDC.	2022-07-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C28 H31 N O5'
_chemical_formula_weight         461.54

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

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   7.6357(4)
_cell_length_b                   17.5288(11)
_cell_length_c                   17.6701(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2365.1(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    137.2(8)
_cell_measurement_reflns_used    2432
_cell_measurement_theta_min      3.5440
_cell_measurement_theta_max      69.6500

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            WHITE
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.296
_exptl_crystal_F_000             984
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.110
_exptl_absorpt_coefficient_mu    0.716
_shelx_estimated_absorpt_T_min   0.919
_shelx_estimated_absorpt_T_max   0.925
_exptl_absorpt_correction_T_min  0.99296
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      137.2(8)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5563
_diffrn_reflns_av_unetI/netI     0.0594
_diffrn_reflns_av_R_equivalents  0.0334
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         3.552
_diffrn_reflns_theta_max         67.233
_diffrn_reflns_theta_full        67.233
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.877
_diffrn_reflns_point_group_measured_fraction_full 0.877
_reflns_number_total             3703
_reflns_number_gt                3277
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.531
_reflns_Friedel_fraction_max     0.713
_reflns_Friedel_fraction_full    0.713

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_structure_solution    'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0435P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1032 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.1(2)
_chemical_absolute_configuration RM
_refine_ls_number_reflns         3703
_refine_ls_number_parameters     311
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0505
_refine_ls_R_factor_gt           0.0430
_refine_ls_wR_factor_ref         0.1021
_refine_ls_wR_factor_gt          0.0968
_refine_ls_goodness_of_fit_ref   1.026
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N -0.3409(4) 0.27054(16) 0.91460(16) 0.0284(7) Uani 1 1 d . . . . .
O1 O -0.4969(3) 0.26465(17) 0.90116(15) 0.0434(7) Uani 1 1 d . . . . .
O2 O -0.2823(3) 0.29568(15) 0.97389(13) 0.0388(6) Uani 1 1 d . . . . .
O3 O 0.0926(3) 0.18652(14) 0.61637(12) 0.0288(6) Uani 1 1 d . . . . .
O4 O 0.3099(3) 0.19182(14) 0.70210(12) 0.0262(5) Uani 1 1 d . . . . .
O5 O 0.7764(3) 0.10412(12) 0.47885(11) 0.0194(5) Uani 1 1 d . . . . .
C1 C -0.2153(4) 0.24602(18) 0.85608(18) 0.0223(7) Uani 1 1 d . . . . .
C2 C -0.0406(4) 0.23993(19) 0.87502(18) 0.0248(8) Uani 1 1 d . . . . .
H2 H -0.003435 0.247642 0.924557 0.030 Uiso 1 1 calc R U . . .
C3 C 0.0776(4) 0.22215(18) 0.81873(18) 0.0241(7) Uani 1 1 d . . . . .
H3 H 0.196012 0.217484 0.830207 0.029 Uiso 1 1 calc R U . . .
C4 C 0.0203(4) 0.21117(18) 0.74488(18) 0.0211(7) Uani 1 1 d . . . . .
C5 C -0.1582(4) 0.2139(2) 0.72842(18) 0.0260(8) Uani 1 1 d . . . . .
H5 H -0.197075 0.204266 0.679473 0.031 Uiso 1 1 calc R U . . .
C6 C -0.2769(4) 0.23094(19) 0.78452(18) 0.0256(7) Uani 1 1 d . . . . .
H6 H -0.396292 0.232218 0.774242 0.031 Uiso 1 1 calc R U . . .
C7 C 0.1405(4) 0.19538(19) 0.67984(18) 0.0222(7) Uani 1 1 d . . . . .
C8 C 0.4289(4) 0.1699(2) 0.64402(18) 0.0231(7) Uani 1 1 d . . . . .
C9 C 0.4898(4) 0.09667(19) 0.64452(17) 0.0229(7) Uani 1 1 d . . . . .
H9 H 0.453492 0.063182 0.682198 0.027 Uiso 1 1 calc R U . . .
C10 C 0.6062(4) 0.07173(18) 0.58896(18) 0.0211(7) Uani 1 1 d . . . . .
C11 C 0.6597(4) 0.12338(19) 0.53449(17) 0.0200(7) Uani 1 1 d . . . . .
C12 C 0.6000(4) 0.19846(19) 0.53523(18) 0.0237(7) Uani 1 1 d . . . . .
H12 H 0.639092 0.232731 0.498767 0.028 Uiso 1 1 calc R U . . .
C13 C 0.4823(4) 0.22224(19) 0.59033(18) 0.0245(7) Uani 1 1 d . . . . .
H13 H 0.440513 0.272078 0.591060 0.029 Uiso 1 1 calc R U . . .
C14 C 0.6655(4) -0.00962(19) 0.58567(19) 0.0250(7) Uani 1 1 d . . . . .
H14A H 0.568217 -0.041052 0.569159 0.030 Uiso 1 1 calc R U . . .
H14B H 0.697530 -0.025917 0.636272 0.030 Uiso 1 1 calc R U . . .
C15 C 0.8223(4) -0.02356(18) 0.53236(18) 0.0226(7) Uani 1 1 d . . . . .
C16 C 0.9925(4) 0.00795(19) 0.56963(18) 0.0242(7) Uani 1 1 d . . . . .
H16 H 0.969075 0.060913 0.584243 0.029 Uiso 1 1 calc R U . . .
C17 C 1.1464(4) 0.0092(2) 0.51445(19) 0.0283(8) Uani 1 1 d . . . . .
H17A H 1.177009 -0.042916 0.501432 0.034 Uiso 1 1 calc R U . . .
H17B H 1.246756 0.031941 0.539375 0.034 Uiso 1 1 calc R U . . .
C18 C 1.1081(4) 0.0533(2) 0.44181(18) 0.0260(8) Uani 1 1 d . . . . .
H18A H 1.208405 0.049517 0.408330 0.031 Uiso 1 1 calc R U . . .
H18B H 1.091567 0.106789 0.454097 0.031 Uiso 1 1 calc R U . . .
C19 C 0.9440(4) 0.02364(18) 0.40014(19) 0.0236(7) Uani 1 1 d . . . . .
C20 C 0.8961(5) 0.0741(2) 0.33266(18) 0.0275(8) Uani 1 1 d . . . . .
C21 C 0.7318(5) 0.0891(2) 0.31426(19) 0.0312(8) Uani 1 1 d . . . . .
H21 H 0.712961 0.117996 0.270879 0.037 Uiso 1 1 calc R U . . .
C22 C 0.5738(5) 0.0635(2) 0.3574(2) 0.0331(8) Uani 1 1 d . . . . .
H22A H 0.488547 0.042766 0.322230 0.040 Uiso 1 1 calc R U . . .
H22B H 0.521042 0.107212 0.382153 0.040 Uiso 1 1 calc R U . . .
C23 C 0.6177(4) 0.0031(2) 0.4169(2) 0.0279(8) Uani 1 1 d . . . . .
H23A H 0.629353 -0.046311 0.392606 0.033 Uiso 1 1 calc R U . . .
H23B H 0.523028 -0.000178 0.453361 0.033 Uiso 1 1 calc R U . . .
C24 C 0.7888(4) 0.02298(18) 0.45793(18) 0.0222(7) Uani 1 1 d . . . . .
C25 C 0.8298(5) -0.11038(19) 0.5207(2) 0.0294(8) Uani 1 1 d . . . . .
H25A H 0.809741 -0.135603 0.568165 0.044 Uiso 1 1 calc R U . . .
H25B H 0.942969 -0.124357 0.501590 0.044 Uiso 1 1 calc R U . . .
H25C H 0.741234 -0.125413 0.485144 0.044 Uiso 1 1 calc R U . . .
C26 C 1.0468(5) -0.0348(2) 0.6413(2) 0.0373(9) Uani 1 1 d . . . . .
H26A H 1.072046 -0.086956 0.628977 0.056 Uiso 1 1 calc R U . . .
H26B H 0.953238 -0.032874 0.677527 0.056 Uiso 1 1 calc R U . . .
H26C H 1.149370 -0.011270 0.662407 0.056 Uiso 1 1 calc R U . . .
C27 C 0.9864(5) -0.0559(2) 0.3663(2) 0.0328(9) Uani 1 1 d . . . . .
H27A H 0.880119 -0.079513 0.349040 0.049 Uiso 1 1 calc R U . . .
H27B H 1.039634 -0.087338 0.404352 0.049 Uiso 1 1 calc R U . . .
H27C H 1.065505 -0.050150 0.324444 0.049 Uiso 1 1 calc R U . . .
C28 C 1.0444(5) 0.1045(2) 0.28512(19) 0.0354(9) Uani 1 1 d . . . . .
H28A H 0.997747 0.131490 0.242383 0.053 Uiso 1 1 calc R U . . .
H28B H 1.115363 0.062788 0.267744 0.053 Uiso 1 1 calc R U . . .
H28C H 1.114711 0.138502 0.314964 0.053 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 O1 1.219(4) . ?
N1 O2 1.222(4) . ?
N1 C1 1.474(4) . ?
O3 C7 1.190(4) . ?
O4 C7 1.354(4) . ?
O4 C8 1.423(4) . ?
O5 C11 1.369(4) . ?
O5 C24 1.473(4) . ?
C1 C6 1.375(4) . ?
C1 C2 1.380(4) . ?
C2 C3 1.379(4) . ?
C3 C4 1.390(4) . ?
C4 C5 1.395(5) . ?
C4 C7 1.497(4) . ?
C5 C6 1.376(4) . ?
C8 C9 1.365(5) . ?
C8 C13 1.382(5) . ?
C9 C10 1.395(4) . ?
C10 C11 1.383(4) . ?
C10 C14 1.497(4) . ?
C11 C12 1.393(5) . ?
C12 C13 1.389(4) . ?
C14 C15 1.542(4) . ?
C15 C25 1.537(4) . ?
C15 C16 1.558(4) . ?
C15 C24 1.569(4) . ?
C16 C17 1.527(4) . ?
C16 C26 1.529(5) . ?
C17 C18 1.527(5) . ?
C18 C19 1.544(4) . ?
C19 C20 1.529(5) . ?
C19 C27 1.552(5) . ?
C19 C24 1.564(4) . ?
C20 C21 1.322(5) . ?
C20 C28 1.507(5) . ?
C21 C22 1.496(5) . ?
C22 C23 1.530(5) . ?
C23 C24 1.535(4) . ?

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
O1 N1 O2 123.8(3) . . ?
O1 N1 C1 118.3(3) . . ?
O2 N1 C1 117.9(3) . . ?
C7 O4 C8 114.4(2) . . ?
C11 O5 C24 117.4(2) . . ?
C6 C1 C2 122.6(3) . . ?
C6 C1 N1 118.6(3) . . ?
C2 C1 N1 118.8(3) . . ?
C3 C2 C1 118.4(3) . . ?
C2 C3 C4 120.2(3) . . ?
C3 C4 C5 119.9(3) . . ?
C3 C4 C7 123.6(3) . . ?
C5 C4 C7 116.5(3) . . ?
C6 C5 C4 120.1(3) . . ?
C1 C6 C5 118.6(3) . . ?
O3 C7 O4 124.2(3) . . ?
O3 C7 C4 124.0(3) . . ?
O4 C7 C4 111.8(3) . . ?
C9 C8 C13 121.9(3) . . ?
C9 C8 O4 117.9(3) . . ?
C13 C8 O4 120.2(3) . . ?
C8 C9 C10 120.5(3) . . ?
C11 C10 C9 118.2(3) . . ?
C11 C10 C14 120.5(3) . . ?
C9 C10 C14 121.2(3) . . ?
O5 C11 C10 122.0(3) . . ?
O5 C11 C12 116.9(3) . . ?
C10 C11 C12 121.0(3) . . ?
C13 C12 C11 120.1(3) . . ?
C8 C13 C12 118.2(3) . . ?
C10 C14 C15 114.2(3) . . ?
C25 C15 C14 105.5(3) . . ?
C25 C15 C16 112.1(3) . . ?
C14 C15 C16 109.4(3) . . ?
C25 C15 C24 114.1(3) . . ?
C14 C15 C24 107.7(3) . . ?
C16 C15 C24 107.8(3) . . ?
C17 C16 C26 109.1(3) . . ?
C17 C16 C15 112.1(3) . . ?
C26 C16 C15 113.8(3) . . ?
C16 C17 C18 113.4(3) . . ?
C17 C18 C19 112.7(3) . . ?
C20 C19 C18 111.8(3) . . ?
C20 C19 C27 105.6(3) . . ?
C18 C19 C27 108.5(3) . . ?
C20 C19 C24 109.4(3) . . ?
C18 C19 C24 107.8(2) . . ?
C27 C19 C24 113.8(3) . . ?
C21 C20 C28 120.4(3) . . ?
C21 C20 C19 122.3(3) . . ?
C28 C20 C19 117.3(3) . . ?
C20 C21 C22 125.5(3) . . ?
C21 C22 C23 112.4(3) . . ?
C22 C23 C24 110.7(3) . . ?
O5 C24 C23 106.5(3) . . ?
O5 C24 C19 101.9(2) . . ?
C23 C24 C19 109.8(3) . . ?
O5 C24 C15 107.6(2) . . ?
C23 C24 C15 114.6(3) . . ?
C19 C24 C15 115.3(3) . . ?

_refine_diff_density_max         0.158
_refine_diff_density_min         -0.191
_refine_diff_density_rms         0.041

