# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 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_qlll1
_audit_block_doi                 10.5517/ccdc.csd.cc25fpfr
_database_code_depnum_ccdc_archive 'CCDC 2009154'
loop_
_audit_author_name
_audit_author_address
'Dandan Liu'
;Kunming Medical University, Chunrong West Street, Yuhua Road, Chenggong District, Kunming, Yunnan
China
;
_audit_update_record             
;
2020-06-10 deposited with the CCDC.	2021-03-02 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C16 H17 N O4'
_chemical_formula_sum            'C16 H17 N O4'
_chemical_formula_iupac          ?
_chemical_formula_weight         287.30
_chemical_absolute_configuration ad

_chemical_melting_point          ?

_space_group_crystal_system      orthorhombic
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
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                   5.2488(2)
_cell_length_b                   7.5956(3)
_cell_length_c                   33.4224(12)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1332.48(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9977
_cell_measurement_theta_min      2.6441
_cell_measurement_theta_max      72.3507
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       prism
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_size_max          0.560
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.070
_exptl_crystal_density_diffrn    1.432
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             608

_exptl_absorpt_coefficient_mu    0.852
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_correction_T_min  0.75
_exptl_absorpt_correction_T_max  0.94

_exptl_special_details           
;
;

_diffrn_ambient_temperature      100.(2)

_diffrn_source                   'Ius Diamond'
_diffrn_source_type              Microfocus

_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_monochromator  'Helixos MX multilayer Optic'

_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON II'
_diffrn_measurement_method       ?

_diffrn_detector_area_resol_mean 7.3910

_diffrn_reflns_number            11774
_diffrn_reflns_av_R_equivalents  0.0324
_diffrn_reflns_av_unetI/netI     0.0227
_diffrn_reflns_theta_min         2.64
_diffrn_reflns_theta_max         72.34
_diffrn_reflns_theta_full        72.34
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_limit_l_max       41

_refine_special_details          
;
;

_reflns_number_total             2637
_reflns_number_gt                2600
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0282
_refine_ls_R_factor_gt           0.0278
_refine_ls_wR_factor_gt          0.0734
_refine_ls_wR_factor_ref         0.0737
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_restrained_S_all      1.057
_refine_ls_number_reflns         2637
_refine_ls_number_parameters     191
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0417P)²+0.2445P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.222
_refine_diff_density_min         -0.169
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
;

Flack x determined using 1031 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.00(5)

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'

_computing_data_collection       'Bruker Instrument Service vV6.2.9'
_computing_cell_refinement       'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 0.6712(3) 0.84689(16) 0.71180(4) 0.0302(3) Uani d . . . 1 . .
O O2 0.8112(3) 0.58788(17) 0.74074(4) 0.0300(3) Uani d . . . 1 . .
O O3 0.1291(2) 0.69300(17) 0.50754(3) 0.0242(3) Uani d . . . 1 . .
H H17 0.011007 0.724947 0.4922 0.036 Uiso calc U . R 1 . .
O O4 0.4242(2) 0.67484(15) 0.57184(3) 0.0216(2) Uani d . . . 1 . .
N N1 0.1940(3) 0.22477(18) 0.60836(4) 0.0206(3) Uani d . . . 1 . .
C C1 -0.0261(3) 0.4109(2) 0.53334(5) 0.0237(3) Uani d . . . 1 . .
H H13 -0.137761 0.398915 0.509627 0.028 Uiso calc U . R 1 . .
H H1 0.137172 0.351236 0.527328 0.028 Uiso calc U . R 1 . .
C C2 -0.1523(3) 0.3211(2) 0.56920(5) 0.0219(3) Uani d . . . 1 . .
H H5 -0.333709 0.359946 0.571596 0.026 Uiso calc U . R 1 . .
C C3 -0.0097(3) 0.3564(2) 0.60860(5) 0.0192(3) Uani d . . . 1 . .
H H15 -0.1269 0.330715 0.63145 0.023 Uiso calc U . R 1 . .
C C4 0.1049(3) 0.5405(2) 0.61452(4) 0.0190(3) Uani d . . . 1 . .
H H16 -0.037196 0.619741 0.623045 0.023 Uiso calc U . R 1 . .
C C5 0.3008(3) 0.5417(2) 0.64788(4) 0.0194(3) Uani d . . . 1 . .
C C6 0.3873(3) 0.7056(2) 0.66223(5) 0.0233(3) Uani d . . . 1 . .
H H4 0.325607 0.812915 0.651288 0.028 Uiso calc U . R 1 . .
C C7 0.5633(3) 0.7051(2) 0.69245(5) 0.0238(3) Uani d . . . 1 . .
C C8 0.8697(3) 0.7715(2) 0.73583(5) 0.0284(4) Uani d . . . 1 . .
H H3 0.877213 0.830516 0.762207 0.034 Uiso calc U . R 1 . .
H H2 1.036685 0.785686 0.722439 0.034 Uiso calc U . R 1 . .
C C9 0.6493(3) 0.5496(2) 0.70956(5) 0.0238(3) Uani d . . . 1 . .
C C10 -0.1388(4) 0.1180(2) 0.56580(5) 0.0276(4) Uani d . . . 1 . .
H H6 -0.304504 0.064303 0.572924 0.033 Uiso calc U . R 1 . .
H H12 -0.093446 0.082272 0.538223 0.033 Uiso calc U . R 1 . .
C C11 0.0687(4) 0.0611(2) 0.59539(5) 0.0283(4) Uani d . . . 1 . .
H H7 -0.00739 -0.000925 0.618548 0.034 Uiso calc U . R 1 . .
H H11 0.192527 -0.018387 0.582252 0.034 Uiso calc U . R 1 . .
C C12 0.3113(3) 0.2085(2) 0.64760(5) 0.0231(3) Uani d . . . 1 . .
H H8 0.461139 0.129751 0.645701 0.028 Uiso calc U . R 1 . .
H H9 0.188188 0.154336 0.666354 0.028 Uiso calc U . R 1 . .
C C13 0.3946(3) 0.3855(2) 0.66387(4) 0.0207(3) Uani d . . . 1 . .
C C14 0.5703(3) 0.3883(2) 0.69591(5) 0.0234(3) Uani d . . . 1 . .
H H10 0.631397 0.282321 0.707563 0.028 Uiso calc U . R 1 . .
C C15 0.0244(3) 0.6069(2) 0.54127(4) 0.0203(3) Uani d . . . 1 . .
H H14 -0.13804 0.66609 0.549231 0.024 Uiso calc U . R 1 . .
C C16 0.2112(3) 0.6150(2) 0.57540(5) 0.0177(3) Uani d . . . 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C7 . 1.378(2) ?
O1 C8 . 1.435(2) ?
O2 C9 . 1.376(2) ?
O2 C8 . 1.437(2) ?
O3 C15 . 1.4147(18) ?
O3 H17 . 0.84 ?
O4 C16 . 1.213(2) ?
N1 C12 . 1.454(2) ?
N1 C3 . 1.464(2) ?
N1 C11 . 1.472(2) ?
C1 C2 . 1.530(2) ?
C1 C15 . 1.535(2) ?
C1 H13 . 0.99 ?
C1 H1 . 0.99 ?
C2 C3 . 1.538(2) ?
C2 C10 . 1.548(2) ?
C2 H5 . 1.0 ?
C3 C4 . 1.535(2) ?
C3 H15 . 1.0 ?
C4 C5 . 1.517(2) ?
C4 C16 . 1.530(2) ?
C4 H16 . 1.0 ?
C5 C13 . 1.392(2) ?
C5 C6 . 1.409(2) ?
C6 C7 . 1.369(2) ?
C6 H4 . 0.95 ?
C7 C9 . 1.388(3) ?
C8 H3 . 0.99 ?
C8 H2 . 0.99 ?
C9 C14 . 1.372(3) ?
C10 C11 . 1.533(2) ?
C10 H6 . 0.99 ?
C10 H12 . 0.99 ?
C11 H7 . 0.99 ?
C11 H11 . 0.99 ?
C12 C13 . 1.514(2) ?
C12 H8 . 0.99 ?
C12 H9 . 0.99 ?
C13 C14 . 1.413(2) ?
C14 H10 . 0.95 ?
C15 C16 . 1.505(2) ?
C15 H14 . 1.0 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C7 O1 C8 . . 104.42(14) ?
C9 O2 C8 . . 104.51(14) ?
C15 O3 H17 . . 109.5 ?
C12 N1 C3 . . 111.24(12) ?
C12 N1 C11 . . 112.52(13) ?
C3 N1 C11 . . 104.60(13) ?
C2 C1 C15 . . 111.83(13) ?
C2 C1 H13 . . 109.3 ?
C15 C1 H13 . . 109.3 ?
C2 C1 H1 . . 109.3 ?
C15 C1 H1 . . 109.3 ?
H13 C1 H1 . . 107.9 ?
C1 C2 C3 . . 112.47(13) ?
C1 C2 C10 . . 111.52(14) ?
C3 C2 C10 . . 102.36(13) ?
C1 C2 H5 . . 110.1 ?
C3 C2 H5 . . 110.1 ?
C10 C2 H5 . . 110.1 ?
N1 C3 C4 . . 109.67(13) ?
N1 C3 C2 . . 103.40(13) ?
C4 C3 C2 . . 117.38(13) ?
N1 C3 H15 . . 108.7 ?
C4 C3 H15 . . 108.7 ?
C2 C3 H15 . . 108.7 ?
C5 C4 C16 . . 112.27(13) ?
C5 C4 C3 . . 111.48(13) ?
C16 C4 C3 . . 111.68(12) ?
C5 C4 H16 . . 107.0 ?
C16 C4 H16 . . 107.0 ?
C3 C4 H16 . . 107.0 ?
C13 C5 C6 . . 120.58(15) ?
C13 C5 C4 . . 121.13(14) ?
C6 C5 C4 . . 118.29(14) ?
C7 C6 C5 . . 117.77(15) ?
C7 C6 H4 . . 121.1 ?
C5 C6 H4 . . 121.1 ?
C6 C7 O1 . . 128.42(16) ?
C6 C7 C9 . . 121.75(16) ?
O1 C7 C9 . . 109.76(14) ?
O1 C8 O2 . . 107.23(14) ?
O1 C8 H3 . . 110.3 ?
O2 C8 H3 . . 110.3 ?
O1 C8 H2 . . 110.3 ?
O2 C8 H2 . . 110.3 ?
H3 C8 H2 . . 108.5 ?
C14 C9 O2 . . 128.87(16) ?
C14 C9 C7 . . 121.66(15) ?
O2 C9 C7 . . 109.46(15) ?
C11 C10 C2 . . 105.45(14) ?
C11 C10 H6 . . 110.7 ?
C2 C10 H6 . . 110.7 ?
C11 C10 H12 . . 110.7 ?
C2 C10 H12 . . 110.7 ?
H6 C10 H12 . . 108.8 ?
N1 C11 C10 . . 105.61(13) ?
N1 C11 H7 . . 110.6 ?
C10 C11 H7 . . 110.6 ?
N1 C11 H11 . . 110.6 ?
C10 C11 H11 . . 110.6 ?
H7 C11 H11 . . 108.8 ?
N1 C12 C13 . . 111.76(13) ?
N1 C12 H8 . . 109.3 ?
C13 C12 H8 . . 109.3 ?
N1 C12 H9 . . 109.3 ?
C13 C12 H9 . . 109.3 ?
H8 C12 H9 . . 107.9 ?
C5 C13 C14 . . 120.59(15) ?
C5 C13 C12 . . 121.12(14) ?
C14 C13 C12 . . 118.29(14) ?
C9 C14 C13 . . 117.57(15) ?
C9 C14 H10 . . 121.2 ?
C13 C14 H10 . . 121.2 ?
O3 C15 C16 . . 109.39(13) ?
O3 C15 C1 . . 112.21(13) ?
C16 C15 C1 . . 106.44(13) ?
O3 C15 H14 . . 109.6 ?
C16 C15 H14 . . 109.6 ?
C1 C15 H14 . . 109.6 ?
O4 C16 C15 . . 122.78(14) ?
O4 C16 C4 . . 123.94(14) ?
C15 C16 C4 . . 113.27(13) ?

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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C15 C1 C2 C3 . . . . -50.74(19) ?
C15 C1 C2 C10 . . . . -165.07(14) ?
C12 N1 C3 C4 . . . . 68.13(16) ?
C11 N1 C3 C4 . . . . -170.14(12) ?
C12 N1 C3 C2 . . . . -165.91(13) ?
C11 N1 C3 C2 . . . . -44.18(15) ?
C1 C2 C3 N1 . . . . -83.32(16) ?
C10 C2 C3 N1 . . . . 36.48(15) ?
C1 C2 C3 C4 . . . . 37.55(19) ?
C10 C2 C3 C4 . . . . 157.35(14) ?
N1 C3 C4 C5 . . . . -45.87(16) ?
C2 C3 C4 C5 . . . . -163.41(13) ?
N1 C3 C4 C16 . . . . 80.62(15) ?
C2 C3 C4 C16 . . . . -36.92(19) ?
C16 C4 C5 C13 . . . . -113.73(16) ?
C3 C4 C5 C13 . . . . 12.4(2) ?
C16 C4 C5 C6 . . . . 65.88(18) ?
C3 C4 C5 C6 . . . . -167.96(14) ?
C13 C5 C6 C7 . . . . -0.7(2) ?
C4 C5 C6 C7 . . . . 179.73(14) ?
C5 C6 C7 O1 . . . . -178.48(15) ?
C5 C6 C7 C9 . . . . -2.0(2) ?
C8 O1 C7 C6 . . . . -171.00(17) ?
C8 O1 C7 C9 . . . . 12.20(18) ?
C7 O1 C8 O2 . . . . -20.54(17) ?
C9 O2 C8 O1 . . . . 21.15(17) ?
C8 O2 C9 C14 . . . . 167.57(17) ?
C8 O2 C9 C7 . . . . -13.70(17) ?
C6 C7 C9 C14 . . . . 2.8(3) ?
O1 C7 C9 C14 . . . . 179.83(15) ?
C6 C7 C9 O2 . . . . -176.07(15) ?
O1 C7 C9 O2 . . . . 0.98(19) ?
C1 C2 C10 C11 . . . . 104.59(16) ?
C3 C2 C10 C11 . . . . -15.87(17) ?
C12 N1 C11 C10 . . . . 154.57(14) ?
C3 N1 C11 C10 . . . . 33.68(17) ?
C2 C10 C11 N1 . . . . -10.00(19) ?
C3 N1 C12 C13 . . . . -52.11(18) ?
C11 N1 C12 C13 . . . . -169.11(14) ?
C6 C5 C13 C14 . . . . 2.7(2) ?
C4 C5 C13 C14 . . . . -177.73(14) ?
C6 C5 C13 C12 . . . . -177.49(15) ?
C4 C5 C13 C12 . . . . 2.1(2) ?
N1 C12 C13 C5 . . . . 17.0(2) ?
N1 C12 C13 C14 . . . . -163.14(14) ?
O2 C9 C14 C13 . . . . 177.89(16) ?
C7 C9 C14 C13 . . . . -0.7(2) ?
C5 C13 C14 C9 . . . . -2.0(2) ?
C12 C13 C14 C9 . . . . 178.21(14) ?
C2 C1 C15 O3 . . . . -176.97(12) ?
C2 C1 C15 C16 . . . . 63.41(17) ?
O3 C15 C16 O4 . . . . -5.5(2) ?
C1 C15 C16 O4 . . . . 115.90(16) ?
O3 C15 C16 C4 . . . . 174.53(13) ?
C1 C15 C16 C4 . . . . -64.03(16) ?
C5 C4 C16 O4 . . . . -2.8(2) ?
C3 C4 C16 O4 . . . . -128.86(15) ?
C5 C4 C16 C15 . . . . 177.13(13) ?
C3 C4 C16 C15 . . . . 51.07(18) ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
O3 H17 O3 2_466 0.84 2.10 2.8091(9) 142.0 ?
O3 H17 O4 2_466 0.84 2.32 3.0334(15) 143.5 ?
C11 H11 O4 1_545 0.99 2.65 3.565(2) 153.6 ?
C15 H14 O3 2_466 1.00 2.50 3.0458(19) 114.1 ?
C15 H14 O4 1_455 1.00 2.42 3.3516(19) 154.8 ?

