# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2021

####################################################################### 
# 
# 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_10415
_database_code_depnum_ccdc_archive 'CCDC 2072646'
loop_
_audit_author_name
_audit_author_address
'Yankai Liu'
;Ocean University of China
China
;
_audit_update_record             
;
2021-03-24 deposited with the CCDC.	2021-06-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H19 N O4'
_chemical_formula_weight         289.32

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'

_symmetry_cell_setting           ?
_symmetry_space_group_name_H-M   ?

loop_
_symmetry_equiv_pos_as_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                   7.2163(4)
_cell_length_b                   10.5180(4)
_cell_length_c                   19.1890(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1456.47(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.21
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.319
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             616
_exptl_absorpt_coefficient_mu    0.780
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  0.8289
_exptl_absorpt_correction_T_max  0.8533
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            9017
_diffrn_reflns_av_R_equivalents  0.0422
_diffrn_reflns_av_sigmaI/netI    0.0355
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         4.61
_diffrn_reflns_theta_max         67.25
_reflns_number_total             2616
_reflns_number_gt                2138
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_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)+(0.0670P)²+0.1290P] 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       0.0100(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.2(4)
_refine_ls_number_reflns         2616
_refine_ls_number_parameters     192
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0569
_refine_ls_R_factor_gt           0.0448
_refine_ls_wR_factor_ref         0.1290
_refine_ls_wR_factor_gt          0.1179
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_restrained_S_all      1.036
_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
N1 N 1.0673(4) 0.5322(3) 0.27270(12) 0.0721(7) Uani 1 1 d . . .
O1 O 0.7186(3) 0.63474(19) 0.47125(9) 0.0606(5) Uani 1 1 d . . .
O2 O 0.6340(3) 0.66035(18) 0.35399(9) 0.0620(5) Uani 1 1 d . . .
O3 O 1.1259(4) 0.4392(3) 0.30220(13) 0.1129(10) Uani 1 1 d . . .
O4 O 1.1039(5) 0.5524(3) 0.21328(12) 0.1317(12) Uani 1 1 d . . .
C1 C 1.3824(4) 0.3679(3) 0.53171(16) 0.0749(9) Uani 1 1 d . . .
H1A H 1.4010 0.3682 0.5812 0.112 Uiso 1 1 calc R . .
H1B H 1.4865 0.4073 0.5093 0.112 Uiso 1 1 calc R . .
H1C H 1.3703 0.2819 0.5156 0.112 Uiso 1 1 calc R . .
C2 C 1.2088(4) 0.4407(2) 0.51441(13) 0.0537(6) Uani 1 1 d . . .
C3 C 1.0543(4) 0.4340(3) 0.55760(13) 0.0571(7) Uani 1 1 d . . .
H3A H 1.0594 0.3843 0.5976 0.068 Uiso 1 1 calc R . .
C4 C 0.8945(4) 0.4993(3) 0.54249(12) 0.0550(7) Uani 1 1 d . . .
H4 H 0.7929 0.4938 0.5722 0.066 Uiso 1 1 calc R . .
C5 C 0.8849(3) 0.5733(2) 0.48295(11) 0.0479(6) Uani 1 1 d . . .
C6 C 1.0361(3) 0.5835(2) 0.43851(11) 0.0447(6) Uani 1 1 d . . .
C7 C 1.1962(4) 0.5179(2) 0.45627(12) 0.0494(6) Uani 1 1 d . . .
H7 H 1.2997 0.5263 0.4278 0.059 Uiso 1 1 calc R . .
C8 C 1.0250(4) 0.6729(2) 0.37746(12) 0.0527(6) Uani 1 1 d . . .
H8 H 1.1482 0.7079 0.3678 0.063 Uiso 1 1 calc R . .
C9 C 0.8945(4) 0.7797(2) 0.39903(13) 0.0628(8) Uani 1 1 d . . .
H9A H 0.9405 0.8217 0.4406 0.075 Uiso 1 1 calc R . .
H9B H 0.8844 0.8422 0.3620 0.075 Uiso 1 1 calc R . .
C10 C 0.7093(4) 0.7202(3) 0.41308(14) 0.0613(8) Uani 1 1 d . . .
H10 H 0.6245 0.7890 0.4261 0.074 Uiso 1 1 calc R . .
C11 C 0.7433(4) 0.5656(2) 0.31718(12) 0.0519(6) Uani 1 1 d . . .
C12 C 0.9396(4) 0.6216(2) 0.30962(12) 0.0553(7) Uani 1 1 d . . .
H12 H 0.9266 0.6954 0.2788 0.066 Uiso 1 1 calc R . .
C13 C 0.6467(5) 0.5502(3) 0.24610(14) 0.0730(9) Uani 1 1 d . . .
H13A H 0.5240 0.5878 0.2473 0.088 Uiso 1 1 calc R . .
H13B H 0.7181 0.5916 0.2098 0.088 Uiso 1 1 calc R . .
C14 C 0.6341(7) 0.4123(3) 0.23268(18) 0.0988(13) Uani 1 1 d . . .
H14A H 0.7426 0.3830 0.2076 0.119 Uiso 1 1 calc R . .
H14B H 0.5248 0.3932 0.2052 0.119 Uiso 1 1 calc R . .
C15 C 0.6225(6) 0.3501(3) 0.30176(17) 0.0957(12) Uani 1 1 d . . .
H15A H 0.6767 0.2658 0.3000 0.115 Uiso 1 1 calc R . .
H15B H 0.4943 0.3426 0.3165 0.115 Uiso 1 1 calc R . .
C16 C 0.7278(4) 0.4329(3) 0.35080(13) 0.0579(7) Uani 1 1 d . . .
H16A H 0.8502 0.3979 0.3590 0.069 Uiso 1 1 calc R . .
H16B H 0.6635 0.4386 0.3951 0.069 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N1 0.0877(19) 0.0819(18) 0.0466(13) -0.0050(13) 0.0138(12) -0.0025(15)
O1 0.0608(11) 0.0704(12) 0.0507(10) -0.0015(9) 0.0058(8) 0.0116(9)
O2 0.0718(12) 0.0573(11) 0.0569(10) -0.0051(9) -0.0107(9) 0.0155(10)
O3 0.139(2) 0.117(2) 0.0829(17) -0.0088(16) 0.0197(16) 0.063(2)
O4 0.200(3) 0.138(3) 0.0576(14) -0.0083(16) 0.0517(17) 0.014(3)
C1 0.077(2) 0.0723(19) 0.076(2) 0.0022(16) -0.0075(16) 0.0156(17)
C2 0.0638(17) 0.0446(12) 0.0528(14) -0.0019(12) -0.0076(12) -0.0026(12)
C3 0.0745(18) 0.0517(14) 0.0451(13) 0.0078(12) -0.0070(13) -0.0072(14)
C4 0.0613(16) 0.0651(15) 0.0387(13) -0.0006(11) 0.0067(12) -0.0093(13)
C5 0.0573(15) 0.0457(12) 0.0406(12) -0.0078(10) 0.0004(10) -0.0014(12)
C6 0.0578(14) 0.0417(12) 0.0346(11) -0.0045(9) 0.0026(10) -0.0071(11)
C7 0.0523(15) 0.0475(13) 0.0484(14) -0.0048(11) 0.0039(11) -0.0038(11)
C8 0.0666(16) 0.0458(13) 0.0458(13) 0.0021(11) 0.0035(11) -0.0115(13)
C9 0.097(2) 0.0390(12) 0.0525(15) -0.0032(11) -0.0050(15) -0.0009(14)
C10 0.078(2) 0.0508(14) 0.0549(15) -0.0093(12) -0.0036(14) 0.0170(14)
C11 0.0670(16) 0.0453(12) 0.0432(12) 0.0009(11) -0.0069(11) 0.0035(13)
C12 0.0830(19) 0.0446(13) 0.0382(12) 0.0043(10) 0.0043(12) -0.0005(13)
C13 0.103(2) 0.0667(19) 0.0493(15) 0.0017(14) -0.0224(15) 0.0098(18)
C14 0.152(4) 0.079(2) 0.065(2) -0.0103(17) -0.032(2) -0.010(3)
C15 0.138(3) 0.0666(19) 0.083(2) 0.0016(18) -0.035(2) -0.028(2)
C16 0.0700(17) 0.0492(14) 0.0544(14) 0.0054(12) -0.0063(13) -0.0040(14)

_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 O4 1.190(3) . ?
N1 O3 1.207(3) . ?
N1 C12 1.496(4) . ?
O1 C5 1.381(3) . ?
O1 C10 1.435(3) . ?
O2 C10 1.406(3) . ?
O2 C11 1.454(3) . ?
C1 C2 1.505(4) . ?
C2 C7 1.383(3) . ?
C2 C3 1.391(4) . ?
C3 C4 1.373(4) . ?
C4 C5 1.384(3) . ?
C5 C6 1.389(3) . ?
C6 C7 1.388(3) . ?
C6 C8 1.504(3) . ?
C8 C9 1.524(4) . ?
C8 C12 1.538(3) . ?
C9 C10 1.500(4) . ?
C11 C13 1.540(3) . ?
C11 C12 1.541(4) . ?
C11 C16 1.542(3) . ?
C13 C14 1.476(5) . ?
C14 C15 1.481(4) . ?
C15 C16 1.490(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
O4 N1 O3 121.2(3) . . ?
O4 N1 C12 118.6(3) . . ?
O3 N1 C12 120.2(2) . . ?
C5 O1 C10 117.40(19) . . ?
C10 O2 C11 119.3(2) . . ?
C7 C2 C3 117.2(2) . . ?
C7 C2 C1 122.1(2) . . ?
C3 C2 C1 120.7(2) . . ?
C4 C3 C2 121.5(2) . . ?
C3 C4 C5 119.8(2) . . ?
O1 C5 C4 116.2(2) . . ?
O1 C5 C6 123.1(2) . . ?
C4 C5 C6 120.7(2) . . ?
C7 C6 C5 117.7(2) . . ?
C7 C6 C8 123.1(2) . . ?
C5 C6 C8 119.0(2) . . ?
C2 C7 C6 123.0(2) . . ?
C6 C8 C9 106.40(19) . . ?
C6 C8 C12 117.5(2) . . ?
C9 C8 C12 103.9(2) . . ?
C10 C9 C8 107.0(2) . . ?
O2 C10 O1 111.4(2) . . ?
O2 C10 C9 112.7(2) . . ?
O1 C10 C9 111.1(2) . . ?
O2 C11 C13 104.9(2) . . ?
O2 C11 C12 106.40(19) . . ?
C13 C11 C12 111.9(2) . . ?
O2 C11 C16 112.2(2) . . ?
C13 C11 C16 104.0(2) . . ?
C12 C11 C16 116.9(2) . . ?
N1 C12 C8 112.0(2) . . ?
N1 C12 C11 111.8(2) . . ?
C8 C12 C11 115.0(2) . . ?
C14 C13 C11 106.6(2) . . ?
C13 C14 C15 106.4(3) . . ?
C14 C15 C16 106.1(3) . . ?
C15 C16 C11 107.6(2) . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        67.25
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.152
_refine_diff_density_min         -0.130
_refine_diff_density_rms         0.037
