# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_11_a
_database_code_depnum_ccdc_archive 'CCDC 1974831'
loop_
_audit_author_name
_audit_author_address
'xiling liu'
;University of Shanghai for Science and Technology 
China
;
_audit_update_record             
;
2019-12-31 deposited with the CCDC.	2020-10-12 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            'C22 H22 N2 O4'
_chemical_formula_weight         378.41

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0137 0.0067 '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 0.0241 0.0134 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0389 0.0241 '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/c'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   13.7287(13)
_cell_length_b                   18.656(2)
_cell_length_c                   7.4592(7)
_cell_angle_alpha                90
_cell_angle_beta                 105.962(6)
_cell_angle_gamma                90
_cell_volume                     1836.8(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    210(2)
_cell_measurement_reflns_used    2282
_cell_measurement_theta_min      2.91
_cell_measurement_theta_max      51.36

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.368
_exptl_crystal_F_000             800
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.070
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    0.493
_shelx_estimated_absorpt_T_min   0.952
_shelx_estimated_absorpt_T_max   0.985
_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      210(2)
_diffrn_radiation_wavelength     1.34139
_diffrn_radiation_type           GaK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14209
_diffrn_reflns_av_unetI/netI     0.0985
_diffrn_reflns_av_R_equivalents  0.0845
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_theta_min         2.913
_diffrn_reflns_theta_max         52.995
_diffrn_reflns_theta_full        52.995
_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 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3252
_reflns_number_gt                1549
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_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)+(0.0903P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.0019(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3252
_refine_ls_number_parameters     256
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1473
_refine_ls_R_factor_gt           0.0616
_refine_ls_wR_factor_ref         0.1823
_refine_ls_wR_factor_gt          0.1407
_refine_ls_goodness_of_fit_ref   0.960
_refine_ls_restrained_S_all      0.960
_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
C1 C 0.1365(3) 0.4934(3) 0.1926(6) 0.0817(16) Uani 1 1 d . . . . .
H1A H 0.117649 0.464192 0.285361 0.123 Uiso 1 1 calc R U . . .
H1B H 0.075822 0.510889 0.103021 0.123 Uiso 1 1 calc R U . . .
H1C H 0.176999 0.533669 0.253199 0.123 Uiso 1 1 calc R U . . .
C2 C 0.1965(3) 0.4493(2) 0.0943(5) 0.0553(12) Uani 1 1 d . . . . .
H2A H 0.214527 0.479468 0.000728 0.066 Uiso 1 1 calc R U . . .
H2B H 0.153191 0.410541 0.027802 0.066 Uiso 1 1 calc R U . . .
C3 C 0.2928(3) 0.4165(2) 0.2179(5) 0.0519(11) Uani 1 1 d . . . . .
H3A H 0.327540 0.451838 0.310753 0.062 Uiso 1 1 calc R U . . .
H3B H 0.275381 0.375298 0.284567 0.062 Uiso 1 1 calc R U . . .
C4 C 0.3636(2) 0.3923(2) 0.1055(5) 0.0437(10) Uani 1 1 d . . . . .
H4A H 0.323123 0.371913 -0.012691 0.052 Uiso 1 1 calc R U . . .
H4B H 0.399341 0.434223 0.076144 0.052 Uiso 1 1 calc R U . . .
C5 C 0.4116(3) 0.2674(2) 0.1705(5) 0.0394(9) Uani 1 1 d . . . . .
C6 C 0.4852(2) 0.2128(2) 0.2588(5) 0.0343(9) Uani 1 1 d . . . . .
C7 C 0.4631(2) 0.1413(2) 0.2219(5) 0.0407(10) Uani 1 1 d . . . . .
H7 H 0.399921 0.127934 0.142373 0.049 Uiso 1 1 calc R U . . .
C8 C 0.5335(2) 0.0892(2) 0.3015(5) 0.0448(10) Uani 1 1 d . . . . .
H8 H 0.519211 0.040722 0.270729 0.054 Uiso 1 1 calc R U . . .
C9 C 0.6244(2) 0.1079(2) 0.4256(5) 0.0404(10) Uani 1 1 d . . . . .
H9 H 0.670271 0.071797 0.482682 0.048 Uiso 1 1 calc R U . . .
C10 C 0.6494(2) 0.1797(2) 0.4679(5) 0.0347(9) Uani 1 1 d . . . . .
C11 C 0.7454(2) 0.2020(2) 0.5949(5) 0.0352(9) Uani 1 1 d . . . . .
C12 C 0.7666(2) 0.2744(2) 0.6205(5) 0.0381(9) Uani 1 1 d . . . . .
H12 H 0.829155 0.289169 0.699586 0.046 Uiso 1 1 calc R U . . .
C13 C 0.6963(2) 0.3255(2) 0.5305(5) 0.0394(9) Uani 1 1 d . . . . .
H13 H 0.712524 0.374237 0.551914 0.047 Uiso 1 1 calc R U . . .
C14 C 0.6036(2) 0.30720(19) 0.4107(5) 0.0335(9) Uani 1 1 d . . . . .
C15 C 0.5328(2) 0.3617(2) 0.3181(5) 0.0343(9) Uani 1 1 d . . . . .
C16 C 0.5797(2) 0.2335(2) 0.3806(4) 0.0319(8) Uani 1 1 d . . . . .
C17 C 0.9104(2) 0.1554(2) 0.8001(5) 0.0382(9) Uani 1 1 d . . . . .
C18 C 0.9823(2) 0.2013(2) 0.7643(5) 0.0458(10) Uani 1 1 d . . . . .
H18 H 0.964087 0.232816 0.662240 0.055 Uiso 1 1 calc R U . . .
C19 C 1.0810(2) 0.2009(2) 0.8781(5) 0.0435(10) Uani 1 1 d . . . . .
H19 H 1.129041 0.232789 0.854389 0.052 Uiso 1 1 calc R U . . .
C20 C 1.1088(2) 0.1540(2) 1.0253(5) 0.0406(10) Uani 1 1 d . . . . .
C21 C 1.0379(3) 0.1079(2) 1.0636(5) 0.0467(10) Uani 1 1 d . . . . .
H21 H 1.056670 0.076255 1.165401 0.056 Uiso 1 1 calc R U . . .
C22 C 0.9389(2) 0.1088(2) 0.9499(5) 0.0438(10) Uani 1 1 d . . . . .
H22 H 0.890707 0.077362 0.974982 0.053 Uiso 1 1 calc R U . . .
N1 N 0.80996(19) 0.14911(17) 0.6849(4) 0.0429(8) Uani 1 1 d . . . . .
H1D H 0.785825 0.105747 0.668889 0.051 Uiso 1 1 calc R U . . .
N2 N 0.43872(18) 0.33881(16) 0.2013(4) 0.0358(8) Uani 1 1 d . . . . .
O1 O 1.20644(16) 0.14859(15) 1.1389(4) 0.0531(8) Uani 1 1 d . . . . .
H1 H 1.240384 0.183055 1.119373 0.080 Uiso 1 1 calc R U . . .
O2 O 0.32682(17) 0.25195(14) 0.0676(3) 0.0532(8) Uani 1 1 d . . . . .
O3 O 0.54819(16) 0.42674(14) 0.3356(3) 0.0447(7) Uani 1 1 d . . . . .
O1W O 0.72843(17) 0.49259(14) 0.3017(3) 0.0528(8) Uani 1 1 d . . . . .
H1WA H 0.664342 0.471778 0.302735 0.063 Uiso 1 1 d R U . . .
H1WB H 0.743742 0.536878 0.369335 0.063 Uiso 1 1 d 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
C1 C2 1.491(5) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C1 H1C 0.9700 . ?
C2 C3 1.518(5) . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C3 C4 1.516(5) . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C4 N2 1.471(4) . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C5 O2 1.239(4) . ?
C5 N2 1.385(5) . ?
C5 C6 1.458(5) . ?
C6 C7 1.379(5) . ?
C6 C16 1.417(4) . ?
C7 C8 1.385(5) . ?
C7 H7 0.9400 . ?
C8 C9 1.379(4) . ?
C8 H8 0.9400 . ?
C9 C10 1.398(5) . ?
C9 H9 0.9400 . ?
C10 C16 1.416(5) . ?
C10 C11 1.455(4) . ?
C11 N1 1.373(4) . ?
C11 C12 1.383(5) . ?
C12 C13 1.390(4) . ?
C12 H12 0.9400 . ?
C13 C14 1.381(4) . ?
C13 H13 0.9400 . ?
C14 C16 1.417(5) . ?
C14 C15 1.444(5) . ?
C15 O3 1.233(4) . ?
C15 N2 1.411(4) . ?
C17 C22 1.384(5) . ?
C17 C18 1.388(5) . ?
C17 N1 1.415(4) . ?
C18 C19 1.387(5) . ?
C18 H18 0.9400 . ?
C19 C20 1.373(5) . ?
C19 H19 0.9400 . ?
C20 O1 1.379(4) . ?
C20 C21 1.386(5) . ?
C21 C22 1.391(4) . ?
C21 H21 0.9400 . ?
C22 H22 0.9400 . ?
N1 H1D 0.8700 . ?
O1 H1 0.8300 . ?
O1W H1WA 0.9637 . ?
O1W H1WB 0.9609 . ?

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
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C1 C2 C3 115.5(3) . . ?
C1 C2 H2A 108.4 . . ?
C3 C2 H2A 108.4 . . ?
C1 C2 H2B 108.4 . . ?
C3 C2 H2B 108.4 . . ?
H2A C2 H2B 107.5 . . ?
C4 C3 C2 111.6(3) . . ?
C4 C3 H3A 109.3 . . ?
C2 C3 H3A 109.3 . . ?
C4 C3 H3B 109.3 . . ?
C2 C3 H3B 109.3 . . ?
H3A C3 H3B 108.0 . . ?
N2 C4 C3 113.8(3) . . ?
N2 C4 H4A 108.8 . . ?
C3 C4 H4A 108.8 . . ?
N2 C4 H4B 108.8 . . ?
C3 C4 H4B 108.8 . . ?
H4A C4 H4B 107.7 . . ?
O2 C5 N2 119.3(3) . . ?
O2 C5 C6 122.3(4) . . ?
N2 C5 C6 118.4(3) . . ?
C7 C6 C16 120.3(3) . . ?
C7 C6 C5 119.9(3) . . ?
C16 C6 C5 119.8(3) . . ?
C6 C7 C8 120.3(3) . . ?
C6 C7 H7 119.9 . . ?
C8 C7 H7 119.9 . . ?
C9 C8 C7 120.4(4) . . ?
C9 C8 H8 119.8 . . ?
C7 C8 H8 119.8 . . ?
C8 C9 C10 121.0(3) . . ?
C8 C9 H9 119.5 . . ?
C10 C9 H9 119.5 . . ?
C9 C10 C16 118.9(3) . . ?
C9 C10 C11 122.9(3) . . ?
C16 C10 C11 118.3(3) . . ?
N1 C11 C12 123.4(3) . . ?
N1 C11 C10 117.4(3) . . ?
C12 C11 C10 119.1(3) . . ?
C11 C12 C13 120.7(3) . . ?
C11 C12 H12 119.6 . . ?
C13 C12 H12 119.6 . . ?
C14 C13 C12 122.5(3) . . ?
C14 C13 H13 118.8 . . ?
C12 C13 H13 118.8 . . ?
C13 C14 C16 118.3(3) . . ?
C13 C14 C15 121.0(3) . . ?
C16 C14 C15 120.7(3) . . ?
O3 C15 N2 117.6(3) . . ?
O3 C15 C14 124.7(3) . . ?
N2 C15 C14 117.7(3) . . ?
C10 C16 C14 121.1(3) . . ?
C10 C16 C6 119.0(3) . . ?
C14 C16 C6 119.9(3) . . ?
C22 C17 C18 119.0(3) . . ?
C22 C17 N1 116.7(3) . . ?
C18 C17 N1 124.1(3) . . ?
C19 C18 C17 120.4(3) . . ?
C19 C18 H18 119.8 . . ?
C17 C18 H18 119.8 . . ?
C20 C19 C18 120.1(3) . . ?
C20 C19 H19 119.9 . . ?
C18 C19 H19 119.9 . . ?
C19 C20 O1 123.2(3) . . ?
C19 C20 C21 120.3(3) . . ?
O1 C20 C21 116.5(3) . . ?
C20 C21 C22 119.4(3) . . ?
C20 C21 H21 120.3 . . ?
C22 C21 H21 120.3 . . ?
C17 C22 C21 120.7(3) . . ?
C17 C22 H22 119.6 . . ?
C21 C22 H22 119.6 . . ?
C11 N1 C17 128.9(3) . . ?
C11 N1 H1D 115.5 . . ?
C17 N1 H1D 115.5 . . ?
C5 N2 C15 123.5(3) . . ?
C5 N2 C4 116.8(3) . . ?
C15 N2 C4 119.7(3) . . ?
C20 O1 H1 109.5 . . ?
H1WA O1W H1WB 114.2 . . ?

_refine_diff_density_max         0.235
_refine_diff_density_min         -0.236
_refine_diff_density_rms         0.058

