# 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_1
_database_code_depnum_ccdc_archive 'CCDC 2258399'
loop_
_audit_author_name
_audit_author_address
'Ruchun Yang'
;Jiangxi Science and Technology Normal University
China
;
_audit_update_record             
;
2023-04-24 deposited with the CCDC.	2023-06-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H19 N O4'
_chemical_formula_weight         325.35

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

_cell_length_a                   10.662(10)
_cell_length_b                   15.838(14)
_cell_length_c                   11.151(10)
_cell_angle_alpha                90
_cell_angle_beta                 113.116(16)
_cell_angle_gamma                90
_cell_volume                     1732(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1762
_cell_measurement_theta_min      2.24
_cell_measurement_theta_max      27.55

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            COLORLESS
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.248
_exptl_crystal_F_000             688
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.160
_exptl_absorpt_coefficient_mu    0.088
_shelx_estimated_absorpt_T_min   0.978
_shelx_estimated_absorpt_T_max   0.986
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8359
_diffrn_reflns_av_unetI/netI     0.1164
_diffrn_reflns_av_R_equivalents  0.0816
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.366
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_full        24.998
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             3034
_reflns_number_gt                1571
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0045P)²+3.0405P] 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_number_reflns         3034
_refine_ls_number_parameters     220
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1697
_refine_ls_R_factor_gt           0.0857
_refine_ls_wR_factor_ref         0.1428
_refine_ls_wR_factor_gt          0.1279
_refine_ls_goodness_of_fit_ref   0.951
_refine_ls_restrained_S_all      0.951
_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 0.6751(3) 0.79819(15) 0.5281(2) 0.0403(7) Uani 1 1 d . . . . .
O2 O 0.9971(3) 0.69261(17) 0.6255(3) 0.0551(8) Uani 1 1 d . . . . .
O3 O 0.8761(3) 0.75154(17) 0.4193(3) 0.0552(8) Uani 1 1 d . . . . .
O4 O 0.5299(3) 0.42304(17) 0.3347(3) 0.0581(8) Uani 1 1 d . . . . .
N1 N 0.7361(4) 0.8388(2) 0.7344(3) 0.0508(9) Uani 1 1 d . . . . .
C13 C 0.7806(4) 0.6319(2) 0.4755(4) 0.0362(10) Uani 1 1 d . . . . .
C16 C 0.6152(4) 0.4898(2) 0.3893(4) 0.0396(10) Uani 1 1 d . . . . .
C6 C 0.5095(4) 0.8822(2) 0.5751(4) 0.0419(10) Uani 1 1 d . . . . .
C9 C 0.8038(4) 0.7662(2) 0.5984(4) 0.0393(10) Uani 1 1 d . . . . .
C7 C 0.6420(4) 0.8413(2) 0.6175(4) 0.0394(10) Uani 1 1 d . . . . .
C10 C 0.8669(4) 0.7109(2) 0.5274(4) 0.0416(10) Uani 1 1 d . . . . .
C14 C 0.6857(4) 0.6269(2) 0.3490(4) 0.0478(11) Uani 1 1 d . . . . .
H14 H 0.6764 0.6716 0.2919 0.057 Uiso 1 1 calc R U . . .
C17 C 0.7080(4) 0.4939(2) 0.5163(4) 0.0438(11) Uani 1 1 d . . . . .
H17 H 0.7165 0.4495 0.5735 0.053 Uiso 1 1 calc R U . . .
C8 C 0.8400(4) 0.7906(2) 0.7219(4) 0.0506(11) Uani 1 1 d . . . . .
H8 H 0.9223 0.7774 0.7898 0.061 Uiso 1 1 calc R U . . .
C18 C 0.7887(4) 0.5651(2) 0.5574(4) 0.0451(11) Uani 1 1 d . . . . .
H18 H 0.8506 0.5681 0.6437 0.054 Uiso 1 1 calc R U . . .
C15 C 0.6040(4) 0.5562(2) 0.3061(4) 0.0497(11) Uani 1 1 d . . . . .
H15 H 0.5409 0.5536 0.2202 0.060 Uiso 1 1 calc R U . . .
C5 C 0.4266(5) 0.8905(3) 0.4447(5) 0.0544(12) Uani 1 1 d . . . . .
H5 H 0.4560 0.8700 0.3820 0.065 Uiso 1 1 calc R U . . .
C1 C 0.4630(5) 0.9130(3) 0.6660(5) 0.0630(13) Uani 1 1 d . . . . .
H1 H 0.5169 0.9078 0.7545 0.076 Uiso 1 1 calc R U . . .
C19 C 0.5319(5) 0.3533(3) 0.4158(5) 0.0672(14) Uani 1 1 d . . . . .
H19A H 0.4682 0.3114 0.3652 0.101 Uiso 1 1 calc R U . . .
H19B H 0.5071 0.3721 0.4854 0.101 Uiso 1 1 calc R U . . .
H19C H 0.6219 0.3295 0.4516 0.101 Uiso 1 1 calc R U . . .
C3 C 0.2552(5) 0.9590(3) 0.4967(6) 0.0738(15) Uani 1 1 d . . . . .
H3 H 0.1698 0.9842 0.4705 0.089 Uiso 1 1 calc R U . . .
C2 C 0.3362(6) 0.9516(3) 0.6260(6) 0.0772(16) Uani 1 1 d . . . . .
H2 H 0.3063 0.9728 0.6880 0.093 Uiso 1 1 calc R U . . .
C4 C 0.3003(5) 0.9291(3) 0.4060(5) 0.0684(14) Uani 1 1 d . . . . .
H4 H 0.2459 0.9346 0.3177 0.082 Uiso 1 1 calc R U . . .
C12 C 0.9482(5) 0.8305(3) 0.4460(5) 0.0843(18) Uani 1 1 d . . . . .
H12A H 0.9567 0.8506 0.3684 0.126 Uiso 1 1 calc R U . . .
H12B H 1.0373 0.8226 0.5133 0.126 Uiso 1 1 calc R U . . .
H12C H 0.8987 0.8711 0.4744 0.126 Uiso 1 1 calc R U . . .
C11 C 1.0848(5) 0.6428(3) 0.5834(5) 0.0814(17) Uani 1 1 d . . . . .
H11A H 1.0965 0.6706 0.5119 0.122 Uiso 1 1 calc R U . . .
H11B H 1.0446 0.5883 0.5557 0.122 Uiso 1 1 calc R U . . .
H11C H 1.1719 0.6363 0.6542 0.122 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
O1 C7 1.365(4) . ?
O1 C9 1.382(4) . ?
O2 C10 1.419(5) . ?
O2 C11 1.437(5) . ?
O3 C10 1.404(4) . ?
O3 C12 1.437(5) . ?
O4 C16 1.372(4) . ?
O4 C19 1.422(5) . ?
N1 C7 1.296(5) . ?
N1 C8 1.397(5) . ?
C13 C14 1.378(5) . ?
C13 C18 1.378(5) . ?
C13 C10 1.526(5) . ?
C16 C17 1.374(5) . ?
C16 C15 1.376(5) . ?
C6 C1 1.380(5) . ?
C6 C5 1.380(5) . ?
C6 C7 1.454(6) . ?
C9 C8 1.333(5) . ?
C9 C10 1.506(5) . ?
C14 C15 1.383(5) . ?
C14 H14 0.9300 . ?
C17 C18 1.383(5) . ?
C17 H17 0.9300 . ?
C8 H8 0.9300 . ?
C18 H18 0.9300 . ?
C15 H15 0.9300 . ?
C5 C4 1.384(6) . ?
C5 H5 0.9300 . ?
C1 C2 1.388(6) . ?
C1 H1 0.9300 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C3 C4 1.364(6) . ?
C3 C2 1.364(7) . ?
C3 H3 0.9300 . ?
C2 H2 0.9300 . ?
C4 H4 0.9300 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 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
C7 O1 C9 104.6(3) . . ?
C10 O2 C11 115.1(3) . . ?
C10 O3 C12 115.6(3) . . ?
C16 O4 C19 118.3(3) . . ?
C7 N1 C8 104.3(3) . . ?
C14 C13 C18 117.7(4) . . ?
C14 C13 C10 121.7(4) . . ?
C18 C13 C10 120.4(4) . . ?
O4 C16 C17 125.2(4) . . ?
O4 C16 C15 115.0(4) . . ?
C17 C16 C15 119.7(4) . . ?
C1 C6 C5 118.3(4) . . ?
C1 C6 C7 120.1(4) . . ?
C5 C6 C7 121.6(4) . . ?
C8 C9 O1 107.5(3) . . ?
C8 C9 C10 134.8(4) . . ?
O1 C9 C10 117.6(3) . . ?
N1 C7 O1 113.5(4) . . ?
N1 C7 C6 127.6(4) . . ?
O1 C7 C6 118.8(4) . . ?
O3 C10 O2 112.3(3) . . ?
O3 C10 C9 112.4(3) . . ?
O2 C10 C9 102.5(3) . . ?
O3 C10 C13 106.6(3) . . ?
O2 C10 C13 112.8(3) . . ?
C9 C10 C13 110.4(3) . . ?
C13 C14 C15 120.6(4) . . ?
C13 C14 H14 119.7 . . ?
C15 C14 H14 119.7 . . ?
C16 C17 C18 118.8(4) . . ?
C16 C17 H17 120.6 . . ?
C18 C17 H17 120.6 . . ?
C9 C8 N1 110.0(4) . . ?
C9 C8 H8 125.0 . . ?
N1 C8 H8 125.0 . . ?
C13 C18 C17 122.5(4) . . ?
C13 C18 H18 118.8 . . ?
C17 C18 H18 118.8 . . ?
C16 C15 C14 120.6(4) . . ?
C16 C15 H15 119.7 . . ?
C14 C15 H15 119.7 . . ?
C6 C5 C4 120.9(4) . . ?
C6 C5 H5 119.6 . . ?
C4 C5 H5 119.6 . . ?
C6 C1 C2 120.3(5) . . ?
C6 C1 H1 119.8 . . ?
C2 C1 H1 119.8 . . ?
O4 C19 H19A 109.5 . . ?
O4 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
O4 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C4 C3 C2 119.5(5) . . ?
C4 C3 H3 120.2 . . ?
C2 C3 H3 120.2 . . ?
C3 C2 C1 120.6(5) . . ?
C3 C2 H2 119.7 . . ?
C1 C2 H2 119.7 . . ?
C3 C4 C5 120.3(5) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 H4 119.8 . . ?
O3 C12 H12A 109.5 . . ?
O3 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
O3 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
O2 C11 H11A 109.5 . . ?
O2 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
O2 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?

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
C19 O4 C16 C17 2.9(6) . . . . ?
C19 O4 C16 C15 -177.7(4) . . . . ?
C7 O1 C9 C8 0.2(4) . . . . ?
C7 O1 C9 C10 176.9(3) . . . . ?
C8 N1 C7 O1 0.1(4) . . . . ?
C8 N1 C7 C6 178.8(4) . . . . ?
C9 O1 C7 N1 -0.2(4) . . . . ?
C9 O1 C7 C6 -179.0(3) . . . . ?
C1 C6 C7 N1 -10.3(6) . . . . ?
C5 C6 C7 N1 170.5(4) . . . . ?
C1 C6 C7 O1 168.3(4) . . . . ?
C5 C6 C7 O1 -10.9(5) . . . . ?
C12 O3 C10 O2 -59.1(5) . . . . ?
C12 O3 C10 C9 55.8(5) . . . . ?
C12 O3 C10 C13 176.9(3) . . . . ?
C11 O2 C10 O3 -56.3(4) . . . . ?
C11 O2 C10 C9 -177.2(3) . . . . ?
C11 O2 C10 C13 64.1(4) . . . . ?
C8 C9 C10 O3 -127.2(5) . . . . ?
O1 C9 C10 O3 57.2(4) . . . . ?
C8 C9 C10 O2 -6.4(6) . . . . ?
O1 C9 C10 O2 178.0(3) . . . . ?
C8 C9 C10 C13 113.9(5) . . . . ?
O1 C9 C10 C13 -61.7(4) . . . . ?
C14 C13 C10 O3 -26.0(5) . . . . ?
C18 C13 C10 O3 158.7(3) . . . . ?
C14 C13 C10 O2 -149.7(4) . . . . ?
C18 C13 C10 O2 35.0(5) . . . . ?
C14 C13 C10 C9 96.3(4) . . . . ?
C18 C13 C10 C9 -79.0(5) . . . . ?
C18 C13 C14 C15 -1.4(6) . . . . ?
C10 C13 C14 C15 -176.8(4) . . . . ?
O4 C16 C17 C18 179.3(4) . . . . ?
C15 C16 C17 C18 -0.1(6) . . . . ?
O1 C9 C8 N1 -0.1(4) . . . . ?
C10 C9 C8 N1 -176.0(4) . . . . ?
C7 N1 C8 C9 0.0(4) . . . . ?
C14 C13 C18 C17 1.6(6) . . . . ?
C10 C13 C18 C17 177.0(4) . . . . ?
C16 C17 C18 C13 -0.8(6) . . . . ?
O4 C16 C15 C14 -179.2(4) . . . . ?
C17 C16 C15 C14 0.2(6) . . . . ?
C13 C14 C15 C16 0.6(6) . . . . ?
C1 C6 C5 C4 0.2(6) . . . . ?
C7 C6 C5 C4 179.5(4) . . . . ?
C5 C6 C1 C2 -0.3(6) . . . . ?
C7 C6 C1 C2 -179.6(4) . . . . ?
C4 C3 C2 C1 -1.0(8) . . . . ?
C6 C1 C2 C3 0.7(8) . . . . ?
C2 C3 C4 C5 0.8(8) . . . . ?
C6 C5 C4 C3 -0.5(7) . . . . ?

_refine_diff_density_max         0.232
_refine_diff_density_min         -0.208
_refine_diff_density_rms         0.046

