# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 2100280'
loop_
_audit_author_name
_audit_author_address
'Hoseop Yun'
;Ajou University
South Korea
;
#Added by publCIF



_audit_update_record             
;
2021-07-30 deposited with the CCDC.	2022-05-19 downloaded from the CCDC.
;


_symmetry_space_group_name_hall  '-C 2yc'
#Added by publCIF




_diffrn_radiation_monochromator  graphite
# publcif _publ_body_element loop end

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H18 O3, C6 H6 N2 O'
_chemical_formula_sum            'C22 H24 N2 O4'
_chemical_formula_weight         380.43

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           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

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

_cell_length_a                   18.2765(12)
_cell_length_b                   6.1664(3)
_cell_length_c                   35.009(2)
_cell_angle_alpha                90
_cell_angle_beta                 90.6002(19)
_cell_angle_gamma                90
_cell_volume                     3945.3(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    290(1)
_cell_measurement_reflns_used    8423
_cell_measurement_theta_min      3.205
_cell_measurement_theta_max      27.43

_exptl_crystal_description       Plate
_exptl_crystal_colour            Colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.281
_exptl_crystal_F_000             1616
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.06
_exptl_absorpt_coefficient_mu    0.089
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(ABSCOR; Higashi, 1995)'
_exptl_absorpt_correction_T_min  0.7811
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      290(1)
_diffrn_radiation_wavelength     0.7107
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Sealed X-ray tube'
_diffrn_measurement_device_type  'Rigaku R-axis Rapid S'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14588
_diffrn_reflns_av_unetI/netI     0.0397
_diffrn_reflns_av_R_equivalents  0.0439
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -43
_diffrn_reflns_limit_l_max       43
_diffrn_reflns_theta_min         3.206
_diffrn_reflns_theta_max         25.998
_diffrn_reflns_theta_full        25.241
_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             3864
_reflns_number_gt                2019
_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    ?
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'
_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)+(0.0790P)²+1.0159P] 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     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.0015(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3864
_refine_ls_number_parameters     256
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1105
_refine_ls_R_factor_gt           0.0489
_refine_ls_wR_factor_ref         0.1792
_refine_ls_wR_factor_gt          0.1314
_refine_ls_goodness_of_fit_ref   1.133
_refine_ls_restrained_S_all      1.133
_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 0.32204(15) 0.4731(4) 0.58824(7) 0.0499(6) Uani 1 1 d . . . . .
C2 C 0.25958(14) 0.3929(4) 0.61285(7) 0.0520(7) Uani 1 1 d . . . . .
H2 H 0.221570 0.505039 0.612556 0.062 Uiso 1 1 calc R U . . .
C3 C 0.22582(17) 0.1870(5) 0.59692(8) 0.0713(9) Uani 1 1 d . . . . .
H3A H 0.262208 0.074806 0.596237 0.107 Uiso 1 1 calc R U . . .
H3B H 0.207623 0.213544 0.571524 0.107 Uiso 1 1 calc R U . . .
H3C H 0.186237 0.142099 0.612907 0.107 Uiso 1 1 calc R U . . .
C4 C 0.28767(14) 0.3716(4) 0.65397(7) 0.0474(6) Uani 1 1 d . . . . .
C5 C 0.27772(15) 0.5384(4) 0.67977(7) 0.0540(7) Uani 1 1 d . . . . .
H5 H 0.253756 0.663664 0.671730 0.065 Uiso 1 1 calc R U . . .
C6 C 0.30229(14) 0.5247(4) 0.71710(7) 0.0528(7) Uani 1 1 d . . . . .
H6 H 0.293969 0.639586 0.733702 0.063 Uiso 1 1 calc R U . . .
C7 C 0.33946(14) 0.3411(4) 0.73036(7) 0.0499(7) Uani 1 1 d . . . . .
C8 C 0.34782(17) 0.1716(5) 0.70448(8) 0.0619(8) Uani 1 1 d . . . . .
H8 H 0.370701 0.044664 0.712569 0.074 Uiso 1 1 calc R U . . .
C9 C 0.32300(16) 0.1866(4) 0.66700(8) 0.0590(7) Uani 1 1 d . . . . .
H9 H 0.330172 0.071015 0.650387 0.071 Uiso 1 1 calc R U . . .
C10 C 0.36688(15) 0.3139(4) 0.76973(7) 0.0551(7) Uani 1 1 d . . . . .
H10 H 0.365476 0.172374 0.778868 0.066 Uiso 1 1 calc R U . . .
C11 C 0.39350(15) 0.4597(4) 0.79451(7) 0.0522(7) Uani 1 1 d . . . . .
C12 C 0.40313(16) 0.6978(4) 0.78736(8) 0.0608(8) Uani 1 1 d . . . . .
H12A H 0.364820 0.777109 0.800295 0.073 Uiso 1 1 calc R U . . .
H12B H 0.398192 0.725979 0.760194 0.073 Uiso 1 1 calc R U . . .
C13 C 0.4771(2) 0.7791(6) 0.80128(10) 0.0861(11) Uani 1 1 d . . . . .
H13A H 0.515096 0.715685 0.785654 0.103 Uiso 1 1 calc R U . . .
H13B H 0.479216 0.935200 0.798068 0.103 Uiso 1 1 calc R U . . .
C14 C 0.4918(2) 0.7260(6) 0.84138(10) 0.0975(13) Uani 1 1 d . . . . .
H14A H 0.457691 0.805110 0.857217 0.117 Uiso 1 1 calc R U . . .
H14B H 0.540783 0.774105 0.848112 0.117 Uiso 1 1 calc R U . . .
C15 C 0.48540(19) 0.4897(6) 0.84999(9) 0.0810(10) Uani 1 1 d . . . . .
H15A H 0.482644 0.471988 0.877465 0.097 Uiso 1 1 calc R U . . .
H15B H 0.529746 0.418298 0.841649 0.097 Uiso 1 1 calc R U . . .
C16 C 0.42098(17) 0.3758(5) 0.83197(8) 0.0634(8) Uani 1 1 d . . . . .
O1 O 0.34318(12) 0.6703(3) 0.59743(5) 0.0662(6) Uani 1 1 d . . . . .
H1 H 0.378248 0.704858 0.584338 0.099 Uiso 1 1 calc R U . . .
O2 O 0.35081(12) 0.3702(3) 0.56329(6) 0.0763(6) Uani 1 1 d . . . . .
O3 O 0.39445(16) 0.2168(4) 0.84697(6) 0.0966(8) Uani 1 1 d . . . . .
C17 C 0.65903(16) 1.0917(5) 0.51905(8) 0.0599(7) Uani 1 1 d . . . . .
C18 C 0.59096(14) 0.9858(4) 0.53368(6) 0.0478(6) Uani 1 1 d . . . . .
C19 C 0.56721(16) 0.7814(4) 0.52345(8) 0.0595(7) Uani 1 1 d . . . . .
H19 H 0.593796 0.697567 0.506413 0.071 Uiso 1 1 calc R U . . .
C20 C 0.50323(17) 0.7035(5) 0.53897(8) 0.0632(8) Uani 1 1 d . . . . .
H20 H 0.487979 0.564737 0.532182 0.076 Uiso 1 1 calc R U . . .
C21 C 0.48618(17) 1.0116(5) 0.57288(8) 0.0680(8) Uani 1 1 d . . . . .
H21 H 0.458581 1.092918 0.589842 0.082 Uiso 1 1 calc R U . . .
C22 C 0.54970(17) 1.0993(5) 0.55913(8) 0.0637(8) Uani 1 1 d . . . . .
H22 H 0.564678 1.236198 0.567155 0.076 Uiso 1 1 calc R U . . .
N1 N 0.69385(13) 1.0012(4) 0.49033(6) 0.0706(7) Uani 1 1 d . . . . .
H1A H 0.732810 1.060530 0.481569 0.085 Uiso 1 1 calc R U . . .
H1B H 0.677581 0.882953 0.480379 0.085 Uiso 1 1 calc R U . . .
N2 N 0.46236(13) 0.8154(4) 0.56299(6) 0.0579(6) Uani 1 1 d . . . . .
O4 O 0.68013(14) 1.2610(4) 0.53428(7) 0.1024(9) 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 O2 1.205(3) . ?
C1 O1 1.315(3) . ?
C1 C2 1.520(4) . ?
C2 C3 1.516(4) . ?
C2 C4 1.529(3) . ?
C2 H2 0.9800 . ?
C3 H3A 0.9600 . ?
C3 H3B 0.9600 . ?
C3 H3C 0.9600 . ?
C4 C5 1.382(4) . ?
C4 C9 1.386(4) . ?
C5 C6 1.380(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.397(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.393(4) . ?
C7 C10 1.471(3) . ?
C8 C9 1.387(4) . ?
C8 H8 0.9300 . ?
C9 H9 0.9300 . ?
C10 C11 1.337(4) . ?
C10 H10 0.9300 . ?
C11 C16 1.492(4) . ?
C11 C12 1.500(4) . ?
C12 C13 1.518(4) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C14 1.464(5) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 C15 1.493(5) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 C16 1.504(4) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 O3 1.215(4) . ?
O1 H1 0.8200 . ?
C17 O4 1.232(3) . ?
C17 N1 1.319(3) . ?
C17 C18 1.500(4) . ?
C18 C22 1.366(4) . ?
C18 C19 1.379(3) . ?
C19 C20 1.381(4) . ?
C19 H19 0.9300 . ?
C20 N2 1.325(4) . ?
C20 H20 0.9300 . ?
C21 N2 1.330(3) . ?
C21 C22 1.372(4) . ?
C21 H21 0.9300 . ?
C22 H22 0.9300 . ?
N1 H1A 0.8600 . ?
N1 H1B 0.8600 . ?

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
O2 C1 O1 122.3(3) . . ?
O2 C1 C2 125.2(2) . . ?
O1 C1 C2 112.5(2) . . ?
C3 C2 C1 111.7(2) . . ?
C3 C2 C4 113.9(2) . . ?
C1 C2 C4 108.4(2) . . ?
C3 C2 H2 107.5 . . ?
C1 C2 H2 107.5 . . ?
C4 C2 H2 107.5 . . ?
C2 C3 H3A 109.5 . . ?
C2 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
C2 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C5 C4 C9 117.5(2) . . ?
C5 C4 C2 120.4(2) . . ?
C9 C4 C2 122.1(2) . . ?
C6 C5 C4 122.0(2) . . ?
C6 C5 H5 119.0 . . ?
C4 C5 H5 119.0 . . ?
C5 C6 C7 121.1(2) . . ?
C5 C6 H6 119.4 . . ?
C7 C6 H6 119.4 . . ?
C8 C7 C6 116.6(2) . . ?
C8 C7 C10 119.0(2) . . ?
C6 C7 C10 124.3(2) . . ?
C9 C8 C7 121.9(3) . . ?
C9 C8 H8 119.1 . . ?
C7 C8 H8 119.1 . . ?
C4 C9 C8 120.9(2) . . ?
C4 C9 H9 119.6 . . ?
C8 C9 H9 119.6 . . ?
C11 C10 C7 130.5(2) . . ?
C11 C10 H10 114.8 . . ?
C7 C10 H10 114.8 . . ?
C10 C11 C16 117.0(2) . . ?
C10 C11 C12 126.3(2) . . ?
C16 C11 C12 116.6(2) . . ?
C11 C12 C13 112.0(2) . . ?
C11 C12 H12A 109.2 . . ?
C13 C12 H12A 109.2 . . ?
C11 C12 H12B 109.2 . . ?
C13 C12 H12B 109.2 . . ?
H12A C12 H12B 107.9 . . ?
C14 C13 C12 112.8(3) . . ?
C14 C13 H13A 109.0 . . ?
C12 C13 H13A 109.0 . . ?
C14 C13 H13B 109.0 . . ?
C12 C13 H13B 109.0 . . ?
H13A C13 H13B 107.8 . . ?
C13 C14 C15 113.4(3) . . ?
C13 C14 H14A 108.9 . . ?
C15 C14 H14A 108.9 . . ?
C13 C14 H14B 108.9 . . ?
C15 C14 H14B 108.9 . . ?
H14A C14 H14B 107.7 . . ?
C14 C15 C16 115.7(3) . . ?
C14 C15 H15A 108.4 . . ?
C16 C15 H15A 108.4 . . ?
C14 C15 H15B 108.4 . . ?
C16 C15 H15B 108.4 . . ?
H15A C15 H15B 107.4 . . ?
O3 C16 C11 121.8(3) . . ?
O3 C16 C15 120.6(3) . . ?
C11 C16 C15 117.5(3) . . ?
C1 O1 H1 109.5 . . ?
O4 C17 N1 122.5(3) . . ?
O4 C17 C18 118.6(2) . . ?
N1 C17 C18 119.0(2) . . ?
C22 C18 C19 117.6(3) . . ?
C22 C18 C17 117.7(2) . . ?
C19 C18 C17 124.7(2) . . ?
C18 C19 C20 118.8(3) . . ?
C18 C19 H19 120.6 . . ?
C20 C19 H19 120.6 . . ?
N2 C20 C19 123.6(3) . . ?
N2 C20 H20 118.2 . . ?
C19 C20 H20 118.2 . . ?
N2 C21 C22 122.9(3) . . ?
N2 C21 H21 118.6 . . ?
C22 C21 H21 118.6 . . ?
C18 C22 C21 120.1(3) . . ?
C18 C22 H22 119.9 . . ?
C21 C22 H22 119.9 . . ?
C17 N1 H1A 120.0 . . ?
C17 N1 H1B 120.0 . . ?
H1A N1 H1B 120.0 . . ?
C20 N2 C21 117.0(3) . . ?

_refine_diff_density_max         0.370
_refine_diff_density_min         -0.256
_refine_diff_density_rms         0.049




_publcif_funding_html            
;
;
