# 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_cu_2021052788D2_0m
_database_code_depnum_ccdc_archive 'CCDC 2133176'
loop_
_audit_author_name
_audit_author_address
'aza-spirobicyclic core'
;Shanghai University of Traditional Chinese Medicine
China
;
_audit_update_record             
;
2022-01-08 deposited with the CCDC.	2022-04-11 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            'C15 H17 N2 O4'
_chemical_formula_weight         289.30

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'
O O 0.0492 0.0322 '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'

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

_cell_length_a                   7.42380(10)
_cell_length_b                   9.5641(2)
_cell_length_c                   20.7146(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1470.78(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    305(2)
_cell_measurement_reflns_used    9990
_cell_measurement_theta_min      4.2686
_cell_measurement_theta_max      65.1033

_exptl_crystal_description       block
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.307
_exptl_crystal_F_000             612
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.795
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      305(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'd8 venture'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15248
_diffrn_reflns_av_unetI/netI     0.0254
_diffrn_reflns_av_R_equivalents  0.0423
_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       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         5.093
_diffrn_reflns_theta_max         65.164
_diffrn_reflns_theta_full        65.164
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             2505
_reflns_number_gt                2407
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.705
_reflns_Friedel_fraction_max     0.999
_reflns_Friedel_fraction_full    0.999

_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2018/2 (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)+(0.0726P)²+0.2147P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 968 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.20(7)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         2505
_refine_ls_number_parameters     198
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0408
_refine_ls_R_factor_gt           0.0391
_refine_ls_wR_factor_ref         0.1132
_refine_ls_wR_factor_gt          0.1109
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_restrained_S_all      1.062
_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
O1 O 1.0809(3) 0.4938(2) 0.42378(11) 0.0675(6) Uani 1 1 d . . . . .
O2 O 0.4145(3) 0.6643(2) 0.28047(11) 0.0619(6) Uani 1 1 d . . . . .
H1B H 0.353(6) 0.730(5) 0.284(2) 0.093 Uiso 1 1 d . U . . .
O3 O 0.7460(3) 0.7182(2) 0.21105(9) 0.0651(6) Uani 1 1 d . . . . .
O4 O 0.7713(4) 1.0059(2) 0.38491(11) 0.0681(6) Uani 1 1 d . . . . .
N2 N 0.7867(3) 0.8816(2) 0.29055(10) 0.0449(5) Uani 1 1 d . . . . .
N13 N 0.3849(3) 0.9115(3) 0.33491(11) 0.0528(6) Uani 1 1 d . . . . .
H1G H 0.415(5) 0.987(4) 0.3126(19) 0.079 Uiso 1 1 d . U . . .
C1 C 0.9306(4) 0.9604(4) 0.25934(16) 0.0668(8) Uani 1 1 d . . . . .
H1 H 1.038753 0.905437 0.258911 0.100 Uiso 1 1 calc R U . . .
H13 H 0.951595 1.045525 0.282749 0.100 Uiso 1 1 calc R U . . .
H12 H 0.896117 0.982255 0.215826 0.100 Uiso 1 1 calc R U . . .
C3 C 0.7091(4) 0.7652(3) 0.26375(11) 0.0446(6) Uani 1 1 d . . . . .
C4 C 0.5741(4) 0.7046(2) 0.31208(12) 0.0431(6) Uani 1 1 d . . . . .
C5 C 0.6604(4) 0.5781(2) 0.34438(11) 0.0424(6) Uani 1 1 d . . . . .
C6 C 0.8316(4) 0.5874(3) 0.37132(12) 0.0465(6) Uani 1 1 d . . . . .
H14 H 0.892837 0.672175 0.370422 0.056 Uiso 1 1 calc R U . . .
C7 C 0.9121(4) 0.4712(3) 0.39959(12) 0.0489(6) Uani 1 1 d . . . . .
C8 C 1.1715(6) 0.3779(4) 0.45182(19) 0.0819(11) Uani 1 1 d . . . . .
H3 H 1.101714 0.342381 0.487233 0.123 Uiso 1 1 calc R U . . .
H2 H 1.287491 0.407105 0.467195 0.123 Uiso 1 1 calc R U . . .
H4 H 1.186351 0.305886 0.419977 0.123 Uiso 1 1 calc R U . . .
C9 C 0.8233(5) 0.3452(3) 0.40031(15) 0.0615(8) Uani 1 1 d . . . . .
H5 H 0.876946 0.266542 0.418366 0.074 Uiso 1 1 calc R U . . .
C10 C 0.6521(5) 0.3373(3) 0.37365(17) 0.0695(9) Uani 1 1 d . . . . .
H16 H 0.590960 0.252425 0.374442 0.083 Uiso 1 1 calc R U . . .
C11 C 0.5710(5) 0.4515(3) 0.34614(15) 0.0585(7) Uani 1 1 d . . . . .
H15 H 0.456021 0.443772 0.328713 0.070 Uiso 1 1 calc R U . . .
C12 C 0.5422(3) 0.8306(2) 0.35877(12) 0.0415(6) Uani 1 1 d . . . . .
C14 C 0.2839(6) 0.9610(5) 0.39166(19) 0.0878(12) Uani 1 1 d . . . . .
H14A H 0.327352 1.051939 0.405413 0.105 Uiso 1 1 calc R U . . .
H14B H 0.156422 0.968172 0.381938 0.105 Uiso 1 1 calc R U . . .
C15 C 0.3151(5) 0.8585(6) 0.44045(17) 0.0891(13) Uani 1 1 d . . . . .
H15A H 0.224178 0.785881 0.438111 0.107 Uiso 1 1 calc R U . . .
H15B H 0.309180 0.901358 0.482847 0.107 Uiso 1 1 calc R U . . .
C16 C 0.4964(4) 0.7978(3) 0.42961(14) 0.0579(8) Uani 1 1 d . . . . .
H10 H 0.494954 0.697667 0.436930 0.069 Uiso 1 1 calc R U . . .
H9 H 0.584032 0.839997 0.458375 0.069 Uiso 1 1 calc R U . . .
C17 C 0.7113(4) 0.9171(3) 0.34944(13) 0.0446(6) 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
O1 C7 1.367(4) . ?
O1 C8 1.420(4) . ?
O2 C4 1.408(3) . ?
O2 H1B 0.78(5) . ?
O3 C3 1.212(3) . ?
O4 C17 1.208(3) . ?
N2 C3 1.371(3) . ?
N2 C17 1.384(3) . ?
N2 C1 1.458(4) . ?
N13 C14 1.473(4) . ?
N13 C12 1.485(3) . ?
N13 H1G 0.88(4) . ?
C1 H1 0.9600 . ?
C1 H13 0.9600 . ?
C1 H12 0.9600 . ?
C3 C4 1.530(4) . ?
C4 C5 1.524(3) . ?
C4 C12 1.564(3) . ?
C5 C11 1.381(4) . ?
C5 C6 1.390(4) . ?
C6 C7 1.391(4) . ?
C6 H14 0.9300 . ?
C7 C9 1.374(4) . ?
C8 H3 0.9600 . ?
C8 H2 0.9600 . ?
C8 H4 0.9600 . ?
C9 C10 1.387(5) . ?
C9 H5 0.9300 . ?
C10 C11 1.372(4) . ?
C10 H16 0.9300 . ?
C11 H15 0.9300 . ?
C12 C17 1.516(4) . ?
C12 C16 1.539(4) . ?
C14 C15 1.427(6) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 C16 1.483(5) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 H10 0.9700 . ?
C16 H9 0.9700 . ?

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
C7 O1 C8 117.4(3) . . ?
C4 O2 H1B 104(4) . . ?
C3 N2 C17 112.7(2) . . ?
C3 N2 C1 123.2(2) . . ?
C17 N2 C1 124.1(2) . . ?
C14 N13 C12 107.6(2) . . ?
C14 N13 H1G 106(3) . . ?
C12 N13 H1G 114(3) . . ?
N2 C1 H1 109.5 . . ?
N2 C1 H13 109.5 . . ?
H1 C1 H13 109.5 . . ?
N2 C1 H12 109.5 . . ?
H1 C1 H12 109.5 . . ?
H13 C1 H12 109.5 . . ?
O3 C3 N2 124.8(3) . . ?
O3 C3 C4 126.6(2) . . ?
N2 C3 C4 108.5(2) . . ?
O2 C4 C5 109.9(2) . . ?
O2 C4 C3 110.5(2) . . ?
C5 C4 C3 108.2(2) . . ?
O2 C4 C12 111.8(2) . . ?
C5 C4 C12 113.85(19) . . ?
C3 C4 C12 102.23(19) . . ?
C11 C5 C6 119.0(2) . . ?
C11 C5 C4 120.4(2) . . ?
C6 C5 C4 120.6(2) . . ?
C5 C6 C7 120.7(2) . . ?
C5 C6 H14 119.6 . . ?
C7 C6 H14 119.6 . . ?
O1 C7 C9 125.1(3) . . ?
O1 C7 C6 115.0(3) . . ?
C9 C7 C6 119.9(3) . . ?
O1 C8 H3 109.5 . . ?
O1 C8 H2 109.5 . . ?
H3 C8 H2 109.5 . . ?
O1 C8 H4 109.5 . . ?
H3 C8 H4 109.5 . . ?
H2 C8 H4 109.5 . . ?
C7 C9 C10 118.9(3) . . ?
C7 C9 H5 120.5 . . ?
C10 C9 H5 120.5 . . ?
C11 C10 C9 121.6(3) . . ?
C11 C10 H16 119.2 . . ?
C9 C10 H16 119.2 . . ?
C10 C11 C5 119.9(3) . . ?
C10 C11 H15 120.1 . . ?
C5 C11 H15 120.1 . . ?
N13 C12 C17 108.97(19) . . ?
N13 C12 C16 104.5(2) . . ?
C17 C12 C16 114.6(2) . . ?
N13 C12 C4 108.3(2) . . ?
C17 C12 C4 102.5(2) . . ?
C16 C12 C4 117.8(2) . . ?
C15 C14 N13 105.2(3) . . ?
C15 C14 H14A 110.7 . . ?
N13 C14 H14A 110.7 . . ?
C15 C14 H14B 110.7 . . ?
N13 C14 H14B 110.7 . . ?
H14A C14 H14B 108.8 . . ?
C14 C15 C16 108.0(3) . . ?
C14 C15 H15A 110.1 . . ?
C16 C15 H15A 110.1 . . ?
C14 C15 H15B 110.1 . . ?
C16 C15 H15B 110.1 . . ?
H15A C15 H15B 108.4 . . ?
C15 C16 C12 105.4(3) . . ?
C15 C16 H10 110.7 . . ?
C12 C16 H10 110.7 . . ?
C15 C16 H9 110.7 . . ?
C12 C16 H9 110.7 . . ?
H10 C16 H9 108.8 . . ?
O4 C17 N2 124.0(3) . . ?
O4 C17 C12 127.7(3) . . ?
N2 C17 C12 108.3(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
C17 N2 C3 O3 176.1(3) . . . . ?
C1 N2 C3 O3 -2.7(4) . . . . ?
C17 N2 C3 C4 -5.3(3) . . . . ?
C1 N2 C3 C4 175.9(2) . . . . ?
O3 C3 C4 O2 -44.2(4) . . . . ?
N2 C3 C4 O2 137.3(2) . . . . ?
O3 C3 C4 C5 76.3(3) . . . . ?
N2 C3 C4 C5 -102.2(2) . . . . ?
O3 C3 C4 C12 -163.3(3) . . . . ?
N2 C3 C4 C12 18.2(2) . . . . ?
O2 C4 C5 C11 -7.3(3) . . . . ?
C3 C4 C5 C11 -128.1(3) . . . . ?
C12 C4 C5 C11 119.0(3) . . . . ?
O2 C4 C5 C6 171.4(2) . . . . ?
C3 C4 C5 C6 50.5(3) . . . . ?
C12 C4 C5 C6 -62.4(3) . . . . ?
C11 C5 C6 C7 0.1(4) . . . . ?
C4 C5 C6 C7 -178.6(2) . . . . ?
C8 O1 C7 C9 0.0(4) . . . . ?
C8 O1 C7 C6 -178.5(3) . . . . ?
C5 C6 C7 O1 179.5(2) . . . . ?
C5 C6 C7 C9 0.9(4) . . . . ?
O1 C7 C9 C10 -179.7(3) . . . . ?
C6 C7 C9 C10 -1.2(4) . . . . ?
C7 C9 C10 C11 0.7(5) . . . . ?
C9 C10 C11 C5 0.2(5) . . . . ?
C6 C5 C11 C10 -0.6(4) . . . . ?
C4 C5 C11 C10 178.1(3) . . . . ?
C14 N13 C12 C17 -106.1(3) . . . . ?
C14 N13 C12 C16 16.8(3) . . . . ?
C14 N13 C12 C4 143.2(3) . . . . ?
O2 C4 C12 N13 -26.2(3) . . . . ?
C5 C4 C12 N13 -151.5(2) . . . . ?
C3 C4 C12 N13 92.0(2) . . . . ?
O2 C4 C12 C17 -141.3(2) . . . . ?
C5 C4 C12 C17 93.4(2) . . . . ?
C3 C4 C12 C17 -23.0(2) . . . . ?
O2 C4 C12 C16 92.0(3) . . . . ?
C5 C4 C12 C16 -33.3(3) . . . . ?
C3 C4 C12 C16 -149.8(2) . . . . ?
C12 N13 C14 C15 -29.6(4) . . . . ?
N13 C14 C15 C16 30.6(5) . . . . ?
C14 C15 C16 C12 -20.0(4) . . . . ?
N13 C12 C16 C15 1.5(3) . . . . ?
C17 C12 C16 C15 120.7(3) . . . . ?
C4 C12 C16 C15 -118.7(3) . . . . ?
C3 N2 C17 O4 171.5(3) . . . . ?
C1 N2 C17 O4 -9.8(4) . . . . ?
C3 N2 C17 C12 -10.8(3) . . . . ?
C1 N2 C17 C12 168.0(2) . . . . ?
N13 C12 C17 O4 84.4(3) . . . . ?
C16 C12 C17 O4 -32.2(4) . . . . ?
C4 C12 C17 O4 -160.9(3) . . . . ?
N13 C12 C17 N2 -93.2(2) . . . . ?
C16 C12 C17 N2 150.2(2) . . . . ?
C4 C12 C17 N2 21.4(2) . . . . ?

_refine_diff_density_max         0.271
_refine_diff_density_min         -0.180
_refine_diff_density_rms         0.051



