# Electronic Supplementary Material (ESI) for Chemical Communications.
# 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_11_a
_database_code_depnum_ccdc_archive 'CCDC 2061389'
loop_
_audit_author_name
_audit_author_address
'H. Liu'
;Shaaxi Normal University
China
;
_audit_update_record             
;
2021-02-05 deposited with the CCDC.	2021-03-15 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 H22 N2 O4'
_chemical_formula_weight         294.34

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                   18.4663(5)
_cell_length_b                   7.8880(2)
_cell_length_c                   10.6546(3)
_cell_angle_alpha                90
_cell_angle_beta                 93.0910(10)
_cell_angle_gamma                90
_cell_volume                     1549.71(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    210(2)
_cell_measurement_reflns_used    9982
_cell_measurement_theta_min      3.49
_cell_measurement_theta_max      53.84

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.262
_exptl_crystal_F_000             632
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.090
_exptl_absorpt_coefficient_mu    0.481
_shelx_estimated_absorpt_T_min   0.945
_shelx_estimated_absorpt_T_max   0.958
_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            12000
_diffrn_reflns_av_unetI/netI     0.0229
_diffrn_reflns_av_R_equivalents  0.0319
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.084
_diffrn_reflns_theta_max         53.860
_diffrn_reflns_theta_full        53.594
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             2815
_reflns_number_gt                2524
_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)+(0.0755P)²+0.3554P] 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     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2815
_refine_ls_number_parameters     195
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0399
_refine_ls_R_factor_gt           0.0356
_refine_ls_wR_factor_ref         0.1080
_refine_ls_wR_factor_gt          0.1032
_refine_ls_goodness_of_fit_ref   0.908
_refine_ls_restrained_S_all      0.908
_refine_ls_shift/su_max          0.001
_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 0.56665(8) 0.3621(2) 0.22253(16) 0.0599(4) Uani 1 1 d . . . . .
H1A H 0.543393 0.311337 0.147848 0.090 Uiso 1 1 calc R U . . .
H1B H 0.615588 0.318261 0.234999 0.090 Uiso 1 1 calc R U . . .
H1C H 0.568370 0.484187 0.212297 0.090 Uiso 1 1 calc R U . . .
C2 C 0.52482(6) 0.32006(18) 0.33309(13) 0.0429(3) Uani 1 1 d . . . . .
H2A H 0.525266 0.197385 0.347657 0.051 Uiso 1 1 calc R U . . .
H2B H 0.546067 0.376337 0.408372 0.051 Uiso 1 1 calc R U . . .
C3 C 0.40518(6) 0.36400(15) 0.39812(11) 0.0345(3) Uani 1 1 d . . . . .
C4 C 0.33181(6) 0.42846(14) 0.36154(11) 0.0308(3) Uani 1 1 d . . . . .
C5 C 0.27794(6) 0.43794(15) 0.45056(11) 0.0321(3) Uani 1 1 d . . . . .
C6 C 0.20936(6) 0.49885(15) 0.40735(11) 0.0325(3) Uani 1 1 d . . . . .
H6 H 0.171922 0.503020 0.463646 0.039 Uiso 1 1 calc R U . . .
C7 C 0.19517(6) 0.55282(14) 0.28475(11) 0.0300(3) Uani 1 1 d . . . . .
C8 C 0.24896(6) 0.54379(14) 0.19513(10) 0.0295(3) Uani 1 1 d . . . . .
C9 C 0.31599(6) 0.48010(14) 0.23730(10) 0.0308(3) Uani 1 1 d . . . . .
H9 H 0.352573 0.471180 0.179633 0.037 Uiso 1 1 calc R U . . .
C10 C 0.17641(7) 0.51039(18) -0.00092(12) 0.0419(3) Uani 1 1 d . . . . .
H10A H 0.191540 0.395420 -0.018448 0.063 Uiso 1 1 calc R U . . .
H10B H 0.165122 0.569390 -0.079427 0.063 Uiso 1 1 calc R U . . .
H10C H 0.133715 0.507559 0.048223 0.063 Uiso 1 1 calc R U . . .
C11 C 0.29776(7) 0.61567(18) -0.00567(12) 0.0404(3) Uani 1 1 d . . . . .
H11A H 0.333847 0.686181 0.038494 0.061 Uiso 1 1 calc R U . . .
H11B H 0.283303 0.667610 -0.085652 0.061 Uiso 1 1 calc R U . . .
H11C H 0.318135 0.504465 -0.020109 0.061 Uiso 1 1 calc R U . . .
C12 C 0.12292(6) 0.63432(15) 0.25677(10) 0.0313(3) Uani 1 1 d . . . . .
C13 C -0.00245(6) 0.61923(18) 0.29796(14) 0.0460(3) Uani 1 1 d . . . . .
H13A H -0.039325 0.529779 0.293607 0.055 Uiso 1 1 calc R U . . .
H13B H -0.009050 0.689112 0.222153 0.055 Uiso 1 1 calc R U . . .
C14 C -0.01185(9) 0.7262(2) 0.41136(16) 0.0604(4) Uani 1 1 d . . . . .
H14A H 0.000621 0.660580 0.486439 0.091 Uiso 1 1 calc R U . . .
H14B H -0.061905 0.763147 0.412574 0.091 Uiso 1 1 calc R U . . .
H14C H 0.019634 0.824447 0.408833 0.091 Uiso 1 1 calc R U . . .
C15 C 0.23908(8) 0.41915(19) 0.66838(12) 0.0460(3) Uani 1 1 d . . . . .
H15A H 0.224675 0.537395 0.668749 0.069 Uiso 1 1 calc R U . . .
H15B H 0.261101 0.389073 0.750066 0.069 Uiso 1 1 calc R U . . .
H15C H 0.196749 0.348713 0.650212 0.069 Uiso 1 1 calc R U . . .
N1 N 0.29059(6) 0.39282(15) 0.57359(10) 0.0420(3) Uani 1 1 d . . . . .
H1 H 0.335339 0.348444 0.593476 0.050 Uiso 1 1 d R U . . .
N2 N 0.23488(5) 0.59883(13) 0.06961(9) 0.0332(2) Uani 1 1 d . . . . .
O1 O 0.45107(4) 0.37896(12) 0.30608(8) 0.0423(2) Uani 1 1 d . . . . .
O2 O 0.42337(5) 0.30356(14) 0.49975(9) 0.0510(3) Uani 1 1 d . . . . .
O3 O 0.11371(5) 0.76744(12) 0.20330(9) 0.0443(3) Uani 1 1 d . . . . .
O4 O 0.06945(4) 0.54306(11) 0.30290(9) 0.0407(2) 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
C1 C2 1.481(2) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C1 H1C 0.9700 . ?
C2 O1 1.4531(14) . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C3 O2 1.2139(15) . ?
C3 O1 1.3353(15) . ?
C3 C4 1.4796(16) . ?
C4 C9 1.4007(16) . ?
C4 C5 1.4131(16) . ?
C5 N1 1.3662(15) . ?
C5 C6 1.4084(16) . ?
C6 C7 1.3854(16) . ?
C6 H6 0.9400 . ?
C7 C8 1.4164(15) . ?
C7 C12 1.4963(15) . ?
C8 C9 1.3879(16) . ?
C8 N2 1.4167(14) . ?
C9 H9 0.9400 . ?
C10 N2 1.4593(16) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 H10C 0.9700 . ?
C11 N2 1.4525(15) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 H11C 0.9700 . ?
C12 O3 1.2024(15) . ?
C12 O4 1.3368(14) . ?
C13 O4 1.4557(14) . ?
C13 C14 1.492(2) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 H14C 0.9700 . ?
C15 N1 1.4393(16) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C15 H15C 0.9700 . ?
N1 H1 0.9117 . ?

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 . . ?
O1 C2 C1 107.13(11) . . ?
O1 C2 H2A 110.3 . . ?
C1 C2 H2A 110.3 . . ?
O1 C2 H2B 110.3 . . ?
C1 C2 H2B 110.3 . . ?
H2A C2 H2B 108.5 . . ?
O2 C3 O1 122.27(11) . . ?
O2 C3 C4 125.12(11) . . ?
O1 C3 C4 112.61(10) . . ?
C9 C4 C5 120.03(10) . . ?
C9 C4 C3 119.36(10) . . ?
C5 C4 C3 120.61(10) . . ?
N1 C5 C6 120.45(10) . . ?
N1 C5 C4 122.69(11) . . ?
C6 C5 C4 116.86(10) . . ?
C7 C6 C5 122.29(10) . . ?
C7 C6 H6 118.9 . . ?
C5 C6 H6 118.9 . . ?
C6 C7 C8 121.08(10) . . ?
C6 C7 C12 116.18(10) . . ?
C8 C7 C12 122.52(10) . . ?
C9 C8 C7 116.46(10) . . ?
C9 C8 N2 122.12(10) . . ?
C7 C8 N2 121.41(10) . . ?
C8 C9 C4 123.24(10) . . ?
C8 C9 H9 118.4 . . ?
C4 C9 H9 118.4 . . ?
N2 C10 H10A 109.5 . . ?
N2 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
N2 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N2 C11 H11A 109.5 . . ?
N2 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
N2 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
O3 C12 O4 123.78(11) . . ?
O3 C12 C7 124.85(10) . . ?
O4 C12 C7 111.33(10) . . ?
O4 C13 C14 110.48(12) . . ?
O4 C13 H13A 109.6 . . ?
C14 C13 H13A 109.6 . . ?
O4 C13 H13B 109.6 . . ?
C14 C13 H13B 109.6 . . ?
H13A C13 H13B 108.1 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
N1 C15 H15A 109.5 . . ?
N1 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
N1 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C5 N1 C15 123.39(10) . . ?
C5 N1 H1 115.4 . . ?
C15 N1 H1 121.2 . . ?
C8 N2 C11 115.96(9) . . ?
C8 N2 C10 115.64(9) . . ?
C11 N2 C10 110.53(10) . . ?
C3 O1 C2 116.84(9) . . ?
C12 O4 C13 117.05(10) . . ?

_refine_diff_density_max         0.165
_refine_diff_density_min         -0.192
_refine_diff_density_rms         0.035

