# 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_11203
_database_code_depnum_ccdc_archive 'CCDC 2050805'
loop_
_audit_author_name
_audit_author_address
'Biao Wang'
;Guangzhou Medical University
China
;
_audit_update_record             
;
2020-12-17 deposited with the CCDC.	2022-01-28 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            'C31 H38 N2 O7'
_chemical_formula_weight         550.63

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

_cell_length_a                   11.0073(4)
_cell_length_b                   13.7688(6)
_cell_length_c                   20.0723(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3042.1(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2954
_cell_measurement_theta_min      3.8620
_cell_measurement_theta_max      70.3580

_exptl_crystal_description       block
_exptl_crystal_colour            white
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.202
_exptl_crystal_F_000             1176
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.110
_exptl_absorpt_coefficient_mu    0.695
_shelx_estimated_absorpt_T_min   0.921
_shelx_estimated_absorpt_T_max   0.927
_exptl_absorpt_correction_T_min  0.96230
_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      293(2)
_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            7222
_diffrn_reflns_av_unetI/netI     0.0497
_diffrn_reflns_av_R_equivalents  0.0273
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.893
_diffrn_reflns_theta_max         67.245
_diffrn_reflns_theta_full        67.245
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.880
_diffrn_reflns_point_group_measured_fraction_full 0.880
_reflns_number_total             4791
_reflns_number_gt                4045
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.560
_reflns_Friedel_fraction_max     0.725
_reflns_Friedel_fraction_full    0.725

_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)+(0.0514P)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     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.0065(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 1229 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.14(15)
_chemical_absolute_configuration rm
_refine_ls_number_reflns         4791
_refine_ls_number_parameters     371
_refine_ls_number_restraints     1356
_refine_ls_R_factor_all          0.0542
_refine_ls_R_factor_gt           0.0442
_refine_ls_wR_factor_ref         0.1119
_refine_ls_wR_factor_gt          0.1040
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_restrained_S_all      0.974
_refine_ls_shift/su_max          0.001
_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 0.0425(3) 0.6489(2) 0.45724(13) 0.0466(7) Uani 1 1 d . U . . .
H1A H -0.012376 0.681515 0.477946 0.056 Uiso 1 1 calc R U . . .
N2 N 0.2332(2) 0.7266(2) 0.19420(12) 0.0406(6) Uani 1 1 d . U . . .
O1 O 0.05481(18) 0.73352(18) 0.25758(11) 0.0454(6) Uani 1 1 d . U . . .
O2 O 0.2685(2) 0.91487(18) 0.33618(13) 0.0555(7) Uani 1 1 d . U . . .
O3 O 0.3635(3) 0.8665(2) 0.42840(12) 0.0644(8) Uani 1 1 d . U . . .
O4 O -0.2587(2) 0.4679(2) 0.33599(15) 0.0638(7) Uani 1 1 d . U . . .
O5 O 0.1366(2) 0.50912(19) 0.24657(12) 0.0556(7) Uani 1 1 d . U . . .
O6 O 0.0730(2) 0.7292(3) 0.12731(12) 0.0766(9) Uani 1 1 d . U . . .
O7 O 0.2571(3) 0.7404(3) 0.08222(12) 0.0799(10) Uani 1 1 d . U . . .
C1 C 0.4578(3) 0.7442(3) 0.17163(18) 0.0521(9) Uani 1 1 d . U . . .
H1 H 0.448830 0.754126 0.126066 0.063 Uiso 1 1 calc R U . . .
C2 C 0.5724(3) 0.7454(3) 0.2013(2) 0.0561(10) Uani 1 1 d . U . . .
H2 H 0.640567 0.756231 0.174962 0.067 Uiso 1 1 calc R U . . .
C3 C 0.5866(3) 0.7310(3) 0.2686(2) 0.0540(9) Uani 1 1 d . U . . .
H3 H 0.663783 0.732392 0.287383 0.065 Uiso 1 1 calc R U . . .
C4 C 0.4861(3) 0.7145(3) 0.30824(19) 0.0470(8) Uani 1 1 d . U . . .
H4 H 0.495746 0.703902 0.353684 0.056 Uiso 1 1 calc R U . . .
C5 C 0.3706(3) 0.7138(2) 0.28020(16) 0.0361(7) Uani 1 1 d . U . . .
C6 C 0.2477(3) 0.7015(2) 0.31076(15) 0.0345(7) Uani 1 1 d . U . . .
C7 C 0.2199(3) 0.7611(2) 0.37504(14) 0.0352(7) Uani 1 1 d . U . . .
H7 H 0.133053 0.776473 0.376772 0.042 Uiso 1 1 calc R U . . .
C8 C 0.2457(3) 0.6720(2) 0.41829(15) 0.0375(7) Uani 1 1 d . U . . .
H8 H 0.331764 0.671151 0.430757 0.045 Uiso 1 1 calc R U . . .
C9 C 0.1684(3) 0.6519(3) 0.47928(16) 0.0462(8) Uani 1 1 d . U . . .
C10 C 0.2054(4) 0.5560(3) 0.5112(2) 0.0678(12) Uani 1 1 d . U . . .
H10A H 0.154790 0.543624 0.549213 0.102 Uiso 1 1 calc R U . . .
H10B H 0.288747 0.559602 0.525061 0.102 Uiso 1 1 calc R U . . .
H10C H 0.195985 0.504438 0.479450 0.102 Uiso 1 1 calc R U . . .
C11 C 0.1812(4) 0.7342(3) 0.52995(17) 0.0671(12) Uani 1 1 d . U . . .
H11A H 0.156580 0.794364 0.509847 0.101 Uiso 1 1 calc R U . . .
H11B H 0.264414 0.739021 0.543931 0.101 Uiso 1 1 calc R U . . .
H11C H 0.130738 0.721031 0.567886 0.101 Uiso 1 1 calc R U . . .
C12 C 0.0123(3) 0.5927(2) 0.40242(15) 0.0382(7) Uani 1 1 d . U . . .
C13 C -0.1086(3) 0.5591(2) 0.39800(17) 0.0437(8) Uani 1 1 d . U . . .
H13 H -0.163527 0.572766 0.431939 0.052 Uiso 1 1 calc R U . . .
C14 C -0.1451(3) 0.5062(3) 0.34360(18) 0.0460(8) Uani 1 1 d . U . . .
C15 C -0.0645(3) 0.4863(3) 0.29208(17) 0.0481(8) Uani 1 1 d . U . . .
H15 H -0.089459 0.450757 0.255149 0.058 Uiso 1 1 calc R U . . .
C16 C 0.0533(3) 0.5202(2) 0.29662(16) 0.0418(8) Uani 1 1 d . U . . .
C17 C 0.0956(3) 0.5717(2) 0.35249(16) 0.0366(7) Uani 1 1 d . U . . .
C18 C 0.2256(3) 0.6061(2) 0.35648(16) 0.0374(7) Uani 1 1 d . U . . .
C19 C 0.3176(3) 0.5236(3) 0.34811(19) 0.0497(9) Uani 1 1 d . U . . .
H19A H 0.293967 0.469543 0.375376 0.075 Uiso 1 1 calc R U . . .
H19B H 0.396671 0.545760 0.361435 0.075 Uiso 1 1 calc R U . . .
H19C H 0.319920 0.503817 0.302269 0.075 Uiso 1 1 calc R U . . .
C20 C 0.1615(3) 0.7207(2) 0.25333(15) 0.0355(7) Uani 1 1 d . U . . .
C21 C 0.3587(3) 0.7280(2) 0.21144(15) 0.0387(7) Uani 1 1 d . U . . .
C22 C 0.1908(3) 0.7336(3) 0.12866(16) 0.0488(8) Uani 1 1 d . U . . .
C23 C 0.0026(4) 0.7342(4) 0.06487(19) 0.0709(13) Uani 1 1 d . U . . .
C24 C 0.0284(6) 0.8259(4) 0.0283(3) 0.109(2) Uani 1 1 d . U . . .
H24A H 0.015820 0.880258 0.057399 0.164 Uiso 1 1 calc R U . . .
H24B H -0.025018 0.830971 -0.009348 0.164 Uiso 1 1 calc R U . . .
H24C H 0.111186 0.825544 0.013170 0.164 Uiso 1 1 calc R U . . .
C25 C 0.0329(6) 0.6489(4) 0.0215(3) 0.112(2) Uani 1 1 d . U . . .
H25A H 0.115505 0.654070 0.006581 0.168 Uiso 1 1 calc R U . . .
H25B H -0.020427 0.648022 -0.016353 0.168 Uiso 1 1 calc R U . . .
H25C H 0.022968 0.589987 0.046485 0.168 Uiso 1 1 calc R U . . .
C26 C -0.1248(5) 0.7316(8) 0.0899(3) 0.170(4) Uani 1 1 d . U . . .
H26A H -0.140909 0.669269 0.109429 0.255 Uiso 1 1 calc R U . . .
H26B H -0.179810 0.742592 0.053617 0.255 Uiso 1 1 calc R U . . .
H26C H -0.135662 0.781328 0.122954 0.255 Uiso 1 1 calc R U . . .
C27 C 0.2925(3) 0.8524(2) 0.38437(16) 0.0412(7) Uani 1 1 d . U . . .
C28 C 0.3437(4) 1.0021(3) 0.3329(2) 0.0633(11) Uani 1 1 d . U . . .
H28A H 0.354763 1.027957 0.377481 0.076 Uiso 1 1 calc R U . . .
H28B H 0.302663 1.051059 0.306445 0.076 Uiso 1 1 calc R U . . .
C29 C 0.4648(4) 0.9809(3) 0.3030(3) 0.0763(13) Uani 1 1 d . U . . .
H29A H 0.509195 0.938007 0.331771 0.114 Uiso 1 1 calc R U . . .
H29B H 0.509167 1.040372 0.297578 0.114 Uiso 1 1 calc R U . . .
H29C H 0.453871 0.950596 0.260323 0.114 Uiso 1 1 calc R U . . .
C30 C -0.3431(3) 0.4835(3) 0.3876(2) 0.0704(12) Uani 1 1 d . U . . .
H30A H -0.311465 0.457549 0.428516 0.106 Uiso 1 1 calc R U . . .
H30B H -0.418155 0.451636 0.376937 0.106 Uiso 1 1 calc R U . . .
H30C H -0.357131 0.551913 0.392700 0.106 Uiso 1 1 calc R U . . .
C31 C 0.1039(5) 0.4544(4) 0.1900(2) 0.0952(18) Uani 1 1 d . U . . .
H31A H 0.078091 0.390857 0.203669 0.143 Uiso 1 1 calc R U . . .
H31B H 0.172647 0.448768 0.160855 0.143 Uiso 1 1 calc R U . . .
H31C H 0.038685 0.486357 0.167044 0.143 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 C12 1.386(4) . ?
N1 C9 1.455(5) . ?
N2 C22 1.399(4) . ?
N2 C21 1.424(4) . ?
N2 C20 1.428(4) . ?
O1 C20 1.191(4) . ?
O2 C27 1.321(4) . ?
O2 C28 1.461(4) . ?
O3 C27 1.196(4) . ?
O4 C14 1.366(4) . ?
O4 C30 1.409(5) . ?
O5 C16 1.369(4) . ?
O5 C31 1.409(5) . ?
O6 C22 1.298(4) . ?
O6 C23 1.475(4) . ?
O7 C22 1.188(4) . ?
C1 C21 1.370(5) . ?
C1 C2 1.395(5) . ?
C2 C3 1.374(6) . ?
C3 C4 1.382(5) . ?
C4 C5 1.390(4) . ?
C5 C21 1.400(4) . ?
C5 C6 1.496(4) . ?
C6 C20 1.516(4) . ?
C6 C7 1.559(4) . ?
C6 C18 1.621(4) . ?
C7 C27 1.501(4) . ?
C7 C8 1.529(4) . ?
C8 C9 1.517(4) . ?
C8 C18 1.553(4) . ?
C9 C10 1.523(5) . ?
C9 C11 1.530(5) . ?
C12 C17 1.389(4) . ?
C12 C13 1.412(5) . ?
C13 C14 1.372(5) . ?
C14 C15 1.390(5) . ?
C15 C16 1.381(5) . ?
C16 C17 1.406(4) . ?
C17 C18 1.509(4) . ?
C18 C19 1.531(5) . ?
C23 C24 1.487(7) . ?
C23 C26 1.490(7) . ?
C23 C25 1.500(7) . ?
C28 C29 1.491(6) . ?

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
C12 N1 C9 119.1(3) . . ?
C22 N2 C21 123.4(3) . . ?
C22 N2 C20 126.9(3) . . ?
C21 N2 C20 109.6(2) . . ?
C27 O2 C28 117.0(3) . . ?
C14 O4 C30 117.6(3) . . ?
C16 O5 C31 118.7(3) . . ?
C22 O6 C23 122.7(3) . . ?
C21 C1 C2 118.2(3) . . ?
C3 C2 C1 121.4(3) . . ?
C2 C3 C4 119.9(3) . . ?
C3 C4 C5 120.0(3) . . ?
C4 C5 C21 118.9(3) . . ?
C4 C5 C6 131.5(3) . . ?
C21 C5 C6 109.6(3) . . ?
C5 C6 C20 103.6(2) . . ?
C5 C6 C7 117.2(3) . . ?
C20 C6 C7 114.5(3) . . ?
C5 C6 C18 117.4(3) . . ?
C20 C6 C18 118.6(2) . . ?
C7 C6 C18 85.9(2) . . ?
C27 C7 C8 120.2(3) . . ?
C27 C7 C6 116.1(2) . . ?
C8 C7 C6 90.6(2) . . ?
C9 C8 C7 120.0(3) . . ?
C9 C8 C18 117.3(3) . . ?
C7 C8 C18 89.4(2) . . ?
N1 C9 C8 107.1(3) . . ?
N1 C9 C10 111.0(3) . . ?
C8 C9 C10 110.3(3) . . ?
N1 C9 C11 108.2(3) . . ?
C8 C9 C11 110.5(3) . . ?
C10 C9 C11 109.8(3) . . ?
N1 C12 C17 122.0(3) . . ?
N1 C12 C13 117.3(3) . . ?
C17 C12 C13 120.6(3) . . ?
C14 C13 C12 120.0(3) . . ?
O4 C14 C13 124.2(3) . . ?
O4 C14 C15 115.2(3) . . ?
C13 C14 C15 120.7(3) . . ?
C16 C15 C14 118.9(3) . . ?
O5 C16 C15 122.9(3) . . ?
O5 C16 C17 114.8(3) . . ?
C15 C16 C17 122.3(3) . . ?
C12 C17 C16 117.5(3) . . ?
C12 C17 C18 121.5(3) . . ?
C16 C17 C18 121.0(3) . . ?
C17 C18 C19 112.9(3) . . ?
C17 C18 C8 111.1(3) . . ?
C19 C18 C8 115.3(3) . . ?
C17 C18 C6 111.5(3) . . ?
C19 C18 C6 116.1(3) . . ?
C8 C18 C6 87.5(2) . . ?
O1 C20 N2 126.6(3) . . ?
O1 C20 C6 126.0(3) . . ?
N2 C20 C6 107.2(2) . . ?
C1 C21 C5 121.5(3) . . ?
C1 C21 N2 129.2(3) . . ?
C5 C21 N2 109.2(3) . . ?
O7 C22 O6 126.9(3) . . ?
O7 C22 N2 122.6(3) . . ?
O6 C22 N2 110.5(3) . . ?
O6 C23 C24 111.0(4) . . ?
O6 C23 C26 101.9(4) . . ?
C24 C23 C26 111.5(6) . . ?
O6 C23 C25 109.9(4) . . ?
C24 C23 C25 109.6(4) . . ?
C26 C23 C25 112.7(6) . . ?
O3 C27 O2 124.5(3) . . ?
O3 C27 C7 125.2(3) . . ?
O2 C27 C7 110.3(3) . . ?
O2 C28 C29 111.3(3) . . ?

_refine_diff_density_max         0.197
_refine_diff_density_min         -0.196
_refine_diff_density_rms         0.033

