# Supplementary Information (SI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2025

####################################################################### 
# 
# 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_t_a
_database_code_depnum_ccdc_archive 'CCDC 2328306'
loop_
_audit_author_name
_audit_author_address
'Lixingzi lixingzi'
;Shang hai jiao tong university
China
;
_audit_update_record             
;
2024-01-25 deposited with the CCDC.	2024-12-13 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         'C22 H20 N2 O5'
_chemical_formula_sum            'C22 H20 N2 O5'
_chemical_formula_weight         392.40

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'

_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                   27.3021(9)
_cell_length_b                   8.3073(3)
_cell_length_c                   17.6695(6)
_cell_angle_alpha                90
_cell_angle_beta                 103.7090(10)
_cell_angle_gamma                90
_cell_volume                     3893.4(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    9844
_cell_measurement_theta_min      5.58
_cell_measurement_theta_max      68.40

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.339
_exptl_crystal_F_000             1648
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    0.793
_shelx_estimated_absorpt_T_min   0.845
_shelx_estimated_absorpt_T_max   0.870
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6439
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction 
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            26425
_diffrn_reflns_av_unetI/netI     0.0197
_diffrn_reflns_av_R_equivalents  0.0348
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         5.435
_diffrn_reflns_theta_max         68.391
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             3528
_reflns_number_gt                3164
_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 2018/2 (Sheldrick, 2018)'
_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)+(0.1000P)²] 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     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3528
_refine_ls_number_parameters     264
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0401
_refine_ls_R_factor_gt           0.0363
_refine_ls_wR_factor_ref         0.1397
_refine_ls_wR_factor_gt          0.1345
_refine_ls_goodness_of_fit_ref   1.223
_refine_ls_restrained_S_all      1.223
_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
O2 O 0.56943(3) 0.94347(12) 0.46579(6) 0.0416(3) Uani 1 1 d . . . . .
O1 O 0.82436(4) 1.15901(13) 0.63302(7) 0.0515(3) Uani 1 1 d . . . . .
O3 O 0.57075(3) 0.77099(10) 0.56455(5) 0.0314(2) Uani 1 1 d . . . . .
O4 O 0.57643(3) 0.52205(12) 0.41663(6) 0.0427(3) Uani 1 1 d . . . . .
O5 O 0.70708(3) 0.48198(11) 0.63226(5) 0.0342(2) Uani 1 1 d . . . . .
N1 N 0.67095(3) 0.70453(11) 0.56061(5) 0.0239(2) Uani 1 1 d . . . . .
N2 N 0.63794(4) 0.46115(12) 0.52732(6) 0.0288(3) Uani 1 1 d . . . . .
C1 C 0.70974(4) 0.82124(13) 0.58355(6) 0.0238(3) Uani 1 1 d . . . . .
C2 C 0.73802(4) 0.83401(15) 0.65962(7) 0.0295(3) Uani 1 1 d . . . . .
H2 H 0.730931 0.765751 0.698825 0.035 Uiso 1 1 calc R U . . .
C3 C 0.77680(5) 0.94660(16) 0.67874(8) 0.0355(3) Uani 1 1 d . . . . .
H3 H 0.796364 0.954679 0.730776 0.043 Uiso 1 1 calc R U . . .
C4 C 0.78673(5) 1.04719(15) 0.62117(8) 0.0352(3) Uani 1 1 d . . . . .
C5 C 0.75766(5) 1.03598(14) 0.54525(8) 0.0313(3) Uani 1 1 d . . . . .
H5 H 0.764005 1.107253 0.506620 0.038 Uiso 1 1 calc R U . . .
C6 C 0.71949(4) 0.92226(14) 0.52496(7) 0.0252(3) Uani 1 1 d . . . . .
C7 C 0.69164(4) 0.89880(15) 0.44429(7) 0.0288(3) Uani 1 1 d . . . . .
H7 H 0.702699 0.952222 0.403795 0.035 Uiso 1 1 calc R U . . .
C8 C 0.65125(4) 0.80467(15) 0.42617(7) 0.0295(3) Uani 1 1 d . . . . .
H8 H 0.635119 0.785054 0.373156 0.035 Uiso 1 1 calc R U . . .
C9 C 0.63128(4) 0.72952(14) 0.48993(6) 0.0256(3) Uani 1 1 d . . . . .
C10 C 0.61087(4) 0.55882(15) 0.47076(7) 0.0292(3) Uani 1 1 d . . . . .
C11 C 0.67585(4) 0.54462(14) 0.58020(6) 0.0251(3) Uani 1 1 d . . . . .
C12 C 0.58690(4) 0.83020(14) 0.50507(7) 0.0265(3) Uani 1 1 d . . . . .
C13 C 0.52628(4) 0.85187(15) 0.57961(7) 0.0316(3) Uani 1 1 d . . . . .
H13A H 0.497596 0.843348 0.533481 0.038 Uiso 1 1 calc R U . . .
H13B H 0.533557 0.967304 0.590905 0.038 Uiso 1 1 calc R U . . .
C14 C 0.51355(5) 0.77090(19) 0.64838(9) 0.0417(3) Uani 1 1 d . . . . .
H14A H 0.483978 0.822950 0.660061 0.062 Uiso 1 1 calc R U . . .
H14B H 0.542215 0.779837 0.693621 0.062 Uiso 1 1 calc R U . . .
H14C H 0.506146 0.657026 0.636395 0.062 Uiso 1 1 calc R U . . .
C15 C 0.86130(6) 1.1531(3) 0.70510(11) 0.0644(5) Uani 1 1 d . . . . .
H15A H 0.889021 1.226548 0.702970 0.097 Uiso 1 1 calc R U . . .
H15B H 0.874355 1.043103 0.714326 0.097 Uiso 1 1 calc R U . . .
H15C H 0.845919 1.185427 0.747541 0.097 Uiso 1 1 calc R U . . .
C16 C 0.62984(5) 0.28793(15) 0.53335(8) 0.0358(3) Uani 1 1 d . . . . .
H16A H 0.662324 0.230781 0.538957 0.043 Uiso 1 1 calc R U . . .
H16B H 0.606539 0.249496 0.484952 0.043 Uiso 1 1 calc R U . . .
C17 C 0.60798(5) 0.24892(14) 0.60238(7) 0.0303(3) Uani 1 1 d . . . . .
C18 C 0.56271(5) 0.31845(15) 0.60874(8) 0.0345(3) Uani 1 1 d . . . . .
H18 H 0.545828 0.392116 0.570168 0.041 Uiso 1 1 calc R U . . .
C19 C 0.54218(5) 0.28049(17) 0.67123(8) 0.0381(3) Uani 1 1 d . . . . .
H19 H 0.511246 0.328118 0.675171 0.046 Uiso 1 1 calc R U . . .
C20 C 0.56644(5) 0.17400(17) 0.72764(8) 0.0394(3) Uani 1 1 d . . . . .
H20 H 0.552263 0.148082 0.770290 0.047 Uiso 1 1 calc R U . . .
C21 C 0.61173(5) 0.10480(17) 0.72178(8) 0.0405(3) Uani 1 1 d . . . . .
H21 H 0.628587 0.031300 0.760457 0.049 Uiso 1 1 calc R U . . .
C22 C 0.63231(5) 0.14308(15) 0.65947(8) 0.0359(3) Uani 1 1 d . . . . .
H22 H 0.663420 0.096174 0.655937 0.043 Uiso 1 1 calc 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
O2 C12 1.1991(15) . ?
O1 C4 1.3639(15) . ?
O1 C15 1.426(2) . ?
O3 C12 1.3267(14) . ?
O3 C13 1.4661(14) . ?
O4 C10 1.2108(14) . ?
O5 C11 1.2134(14) . ?
N1 C11 1.3713(15) . ?
N1 C1 1.4222(14) . ?
N1 C9 1.4611(14) . ?
N2 C10 1.3613(16) . ?
N2 C11 1.4023(15) . ?
N2 C16 1.4636(16) . ?
C1 C2 1.3863(16) . ?
C1 C6 1.4063(16) . ?
C2 C3 1.3931(18) . ?
C3 C4 1.392(2) . ?
C4 C5 1.3905(19) . ?
C5 C6 1.3893(17) . ?
C6 C7 1.4609(16) . ?
C7 C8 1.3275(17) . ?
C8 C9 1.4991(16) . ?
C9 C10 1.5319(16) . ?
C9 C12 1.5470(15) . ?
C13 C14 1.4999(18) . ?
C16 C17 1.5147(17) . ?
C17 C22 1.3835(18) . ?
C17 C18 1.3926(17) . ?
C18 C19 1.3879(18) . ?
C19 C20 1.379(2) . ?
C20 C21 1.389(2) . ?
C21 C22 1.386(2) . ?

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
C4 O1 C15 117.46(13) . . ?
C12 O3 C13 114.77(9) . . ?
C11 N1 C1 124.54(9) . . ?
C11 N1 C9 111.20(9) . . ?
C1 N1 C9 119.86(9) . . ?
C10 N2 C11 112.39(10) . . ?
C10 N2 C16 125.05(11) . . ?
C11 N2 C16 122.55(11) . . ?
C2 C1 C6 120.60(11) . . ?
C2 C1 N1 122.31(10) . . ?
C6 C1 N1 117.07(10) . . ?
C1 C2 C3 120.21(11) . . ?
C4 C3 C2 119.63(11) . . ?
O1 C4 C5 115.51(12) . . ?
O1 C4 C3 124.53(12) . . ?
C5 C4 C3 119.96(11) . . ?
C6 C5 C4 121.08(11) . . ?
C5 C6 C1 118.49(11) . . ?
C5 C6 C7 121.85(11) . . ?
C1 C6 C7 119.55(10) . . ?
C8 C7 C6 121.62(11) . . ?
C7 C8 C9 119.56(10) . . ?
N1 C9 C8 111.94(9) . . ?
N1 C9 C10 102.39(9) . . ?
C8 C9 C10 113.42(10) . . ?
N1 C9 C12 112.41(9) . . ?
C8 C9 C12 110.13(9) . . ?
C10 C9 C12 106.25(9) . . ?
O4 C10 N2 127.91(12) . . ?
O4 C10 C9 125.58(11) . . ?
N2 C10 C9 106.48(9) . . ?
O5 C11 N1 128.00(11) . . ?
O5 C11 N2 124.62(11) . . ?
N1 C11 N2 107.36(9) . . ?
O2 C12 O3 126.03(11) . . ?
O2 C12 C9 122.99(11) . . ?
O3 C12 C9 110.95(9) . . ?
O3 C13 C14 107.60(10) . . ?
N2 C16 C17 111.36(10) . . ?
C22 C17 C18 119.12(12) . . ?
C22 C17 C16 120.69(11) . . ?
C18 C17 C16 120.19(12) . . ?
C19 C18 C17 120.22(12) . . ?
C20 C19 C18 120.35(12) . . ?
C19 C20 C21 119.68(13) . . ?
C22 C21 C20 119.96(13) . . ?
C17 C22 C21 120.66(12) . . ?

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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C11 N1 C1 C2 -47.28(15) . . . . ?
C9 N1 C1 C2 158.39(10) . . . . ?
C11 N1 C1 C6 131.05(11) . . . . ?
C9 N1 C1 C6 -23.28(14) . . . . ?
C6 C1 C2 C3 -0.51(17) . . . . ?
N1 C1 C2 C3 177.76(10) . . . . ?
C1 C2 C3 C4 0.54(18) . . . . ?
C15 O1 C4 C5 -167.57(12) . . . . ?
C15 O1 C4 C3 11.66(19) . . . . ?
C2 C3 C4 O1 -178.54(11) . . . . ?
C2 C3 C4 C5 0.65(18) . . . . ?
O1 C4 C5 C6 177.36(11) . . . . ?
C3 C4 C5 C6 -1.90(18) . . . . ?
C4 C5 C6 C1 1.90(16) . . . . ?
C4 C5 C6 C7 -174.32(10) . . . . ?
C2 C1 C6 C5 -0.70(16) . . . . ?
N1 C1 C6 C5 -179.06(9) . . . . ?
C2 C1 C6 C7 175.61(10) . . . . ?
N1 C1 C6 C7 -2.75(14) . . . . ?
C5 C6 C7 C8 -171.57(11) . . . . ?
C1 C6 C7 C8 12.25(16) . . . . ?
C6 C7 C8 C9 4.46(17) . . . . ?
C11 N1 C9 C8 -119.58(10) . . . . ?
C1 N1 C9 C8 37.92(13) . . . . ?
C11 N1 C9 C10 2.23(11) . . . . ?
C1 N1 C9 C10 159.73(9) . . . . ?
C11 N1 C9 C12 115.85(10) . . . . ?
C1 N1 C9 C12 -86.65(12) . . . . ?
C7 C8 C9 N1 -28.10(15) . . . . ?
C7 C8 C9 C10 -143.34(11) . . . . ?
C7 C8 C9 C12 97.73(13) . . . . ?
C11 N2 C10 O4 178.88(12) . . . . ?
C16 N2 C10 O4 -0.35(19) . . . . ?
C11 N2 C10 C9 -2.93(12) . . . . ?
C16 N2 C10 C9 177.84(10) . . . . ?
N1 C9 C10 O4 178.67(11) . . . . ?
C8 C9 C10 O4 -60.54(16) . . . . ?
C12 C9 C10 O4 60.59(15) . . . . ?
N1 C9 C10 N2 0.43(12) . . . . ?
C8 C9 C10 N2 121.23(10) . . . . ?
C12 C9 C10 N2 -117.64(10) . . . . ?
C1 N1 C11 O5 18.65(18) . . . . ?
C9 N1 C11 O5 174.90(11) . . . . ?
C1 N1 C11 N2 -160.26(9) . . . . ?
C9 N1 C11 N2 -4.01(12) . . . . ?
C10 N2 C11 O5 -174.56(11) . . . . ?
C16 N2 C11 O5 4.70(17) . . . . ?
C10 N2 C11 N1 4.40(12) . . . . ?
C16 N2 C11 N1 -176.35(9) . . . . ?
C13 O3 C12 O2 2.30(17) . . . . ?
C13 O3 C12 C9 -175.77(9) . . . . ?
N1 C9 C12 O2 131.25(12) . . . . ?
C8 C9 C12 O2 5.69(16) . . . . ?
C10 C9 C12 O2 -117.52(13) . . . . ?
N1 C9 C12 O3 -50.61(12) . . . . ?
C8 C9 C12 O3 -176.17(9) . . . . ?
C10 C9 C12 O3 60.61(12) . . . . ?
C12 O3 C13 C14 -179.66(10) . . . . ?
C10 N2 C16 C17 -109.98(13) . . . . ?
C11 N2 C16 C17 70.87(14) . . . . ?
N2 C16 C17 C22 -123.09(13) . . . . ?
N2 C16 C17 C18 57.49(16) . . . . ?
C22 C17 C18 C19 -0.62(18) . . . . ?
C16 C17 C18 C19 178.81(11) . . . . ?
C17 C18 C19 C20 0.2(2) . . . . ?
C18 C19 C20 C21 0.1(2) . . . . ?
C19 C20 C21 C22 0.1(2) . . . . ?
C18 C17 C22 C21 0.80(19) . . . . ?
C16 C17 C22 C21 -178.62(12) . . . . ?
C20 C21 C22 C17 -0.5(2) . . . . ?

_refine_diff_density_max         0.264
_refine_diff_density_min         -0.219
_refine_diff_density_rms         0.039



####################################################################### 
# 
# 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_t_a_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2333917'
loop_
_audit_author_name
_audit_author_address
'Lixingzi lixingzi'
;Shang hai jiao tong university
China
;
_audit_update_record             
;
2024-02-20 deposited with the CCDC.	2024-12-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/1
_shelx_SHELXL_version_number     2019/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H16 N2 O4'
_chemical_formula_sum            'C16 H16 N2 O4'
_chemical_formula_weight         300.31

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

_cell_length_a                   13.0389(3)
_cell_length_b                   6.6376(2)
_cell_length_c                   17.0474(4)
_cell_angle_alpha                90
_cell_angle_beta                 91.1030(10)
_cell_angle_gamma                90
_cell_volume                     1475.13(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    7510
_cell_measurement_theta_min      4.23
_cell_measurement_theta_max      68.34

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.352
_exptl_crystal_F_000             632
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.160
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.816
_shelx_estimated_absorpt_T_min   0.880
_shelx_estimated_absorpt_T_max   0.908
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6123
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14811
_diffrn_reflns_av_unetI/netI     0.0455
_diffrn_reflns_av_R_equivalents  0.0561
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         4.230
_diffrn_reflns_theta_max         68.340
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             2676
_reflns_number_gt                2195
_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-2019/1 (Sheldrick, 2019)'
_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)+(0.0650P)²+0.2256P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2019/1 (Sheldrick 2019)'
_refine_ls_extinction_coef       0.0034(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2676
_refine_ls_number_parameters     204
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0591
_refine_ls_R_factor_gt           0.0359
_refine_ls_wR_factor_ref         0.1083
_refine_ls_wR_factor_gt          0.1010
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_restrained_S_all      1.024
_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
O2 O 0.52575(8) 0.88486(15) 0.60352(6) 0.0356(3) Uani 1 1 d . . . . .
H5 H 0.5548(16) 1.003(3) 0.5975(11) 0.053 Uiso 1 1 d . U . . .
O3 O 0.38814(8) 0.59029(16) 0.69685(7) 0.0394(3) Uani 1 1 d . . . . .
O4 O 0.44428(8) 0.86432(15) 0.76227(6) 0.0334(3) Uani 1 1 d . . . . .
O1 O 0.61813(8) 0.23850(14) 0.58493(6) 0.0338(3) Uani 1 1 d . . . . .
N1 N 0.61360(9) 0.58451(16) 0.57933(7) 0.0281(3) Uani 1 1 d . . . . .
N2 N 0.58516(9) 0.43890(16) 0.69272(7) 0.0268(3) Uani 1 1 d . . . . .
C1 C 0.58833(12) 0.2977(2) 0.75282(9) 0.0341(3) Uani 1 1 d . . . . .
H1 H 0.572136 0.160442 0.742746 0.041 Uiso 1 1 calc R U . . .
C2 C 0.61454(12) 0.3587(2) 0.82488(9) 0.0398(4) Uani 1 1 d . . . . .
H2 H 0.609890 0.269057 0.868099 0.048 Uiso 1 1 calc R U . . .
C3 C 0.65031(11) 0.5638(2) 0.83663(9) 0.0368(4) Uani 1 1 d . . . . .
H3 H 0.684849 0.598340 0.884338 0.044 Uiso 1 1 calc R U . . .
C4 C 0.63569(11) 0.7046(2) 0.78191(9) 0.0313(3) Uani 1 1 d . . . . .
H4 H 0.665076 0.834792 0.787714 0.038 Uiso 1 1 calc R U . . .
C5 C 0.57100(10) 0.65151(18) 0.71021(8) 0.0241(3) Uani 1 1 d . . . . .
C6 C 0.60194(10) 0.75512(18) 0.63186(8) 0.0249(3) Uani 1 1 d . . . . .
H6 H 0.668495 0.828457 0.638788 0.030 Uiso 1 1 calc R U . . .
C7 C 0.60633(10) 0.40459(19) 0.61542(8) 0.0246(3) Uani 1 1 d . . . . .
C8 C 0.45592(10) 0.69418(19) 0.72222(8) 0.0261(3) Uani 1 1 d . . . . .
C9 C 0.33960(13) 0.9340(3) 0.77039(10) 0.0459(4) Uani 1 1 d . . . . .
H9A H 0.339560 1.061919 0.799075 0.069 Uiso 1 1 calc R U . . .
H9B H 0.300291 0.833496 0.799316 0.069 Uiso 1 1 calc R U . . .
H9C H 0.308199 0.953572 0.718253 0.069 Uiso 1 1 calc R U . . .
C10 C 0.62660(12) 0.6091(2) 0.49516(8) 0.0305(3) Uani 1 1 d . . . . .
H10A H 0.567213 0.684458 0.473099 0.037 Uiso 1 1 calc R U . . .
H10B H 0.627256 0.474509 0.470127 0.037 Uiso 1 1 calc R U . . .
C11 C 0.72364(11) 0.7187(2) 0.47537(8) 0.0295(3) Uani 1 1 d . . . . .
C12 C 0.71855(15) 0.9165(2) 0.44946(9) 0.0418(4) Uani 1 1 d . . . . .
H12 H 0.654094 0.982937 0.445834 0.050 Uiso 1 1 calc R U . . .
C13 C 0.8066(2) 1.0175(3) 0.42891(11) 0.0645(6) Uani 1 1 d . . . . .
H13 H 0.802298 1.152752 0.410897 0.077 Uiso 1 1 calc R U . . .
C14 C 0.89951(19) 0.9243(5) 0.43432(12) 0.0762(8) Uani 1 1 d . . . . .
H14 H 0.959762 0.994465 0.419859 0.091 Uiso 1 1 calc R U . . .
C15 C 0.90628(16) 0.7303(5) 0.46047(13) 0.0722(7) Uani 1 1 d . . . . .
H15 H 0.971392 0.666463 0.464449 0.087 Uiso 1 1 calc R U . . .
C16 C 0.81801(13) 0.6245(3) 0.48148(10) 0.0480(4) Uani 1 1 d . . . . .
H16 H 0.822942 0.489567 0.499720 0.058 Uiso 1 1 calc 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
O2 C6 1.3941(16) . ?
O3 C8 1.1955(17) . ?
O4 C8 1.3299(16) . ?
O4 C9 1.4502(18) . ?
O1 C7 1.2298(16) . ?
N1 C7 1.3476(17) . ?
N1 C6 1.4535(17) . ?
N1 C10 1.4573(18) . ?
N2 C7 1.3706(18) . ?
N2 C1 1.3886(17) . ?
N2 C5 1.4549(16) . ?
C1 C2 1.332(2) . ?
C2 C3 1.452(2) . ?
C3 C4 1.331(2) . ?
C4 C5 1.5132(18) . ?
C5 C8 1.5445(18) . ?
C5 C6 1.5621(19) . ?
C10 C11 1.504(2) . ?
C11 C16 1.382(2) . ?
C11 C12 1.387(2) . ?
C12 C13 1.380(3) . ?
C13 C14 1.362(4) . ?
C14 C15 1.365(4) . ?
C15 C16 1.400(3) . ?

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
C8 O4 C9 115.89(12) . . ?
C7 N1 C6 113.58(11) . . ?
C7 N1 C10 124.00(11) . . ?
C6 N1 C10 122.35(11) . . ?
C7 N2 C1 126.41(11) . . ?
C7 N2 C5 112.76(10) . . ?
C1 N2 C5 120.38(12) . . ?
C2 C1 N2 118.60(14) . . ?
C1 C2 C3 119.25(14) . . ?
C4 C3 C2 121.33(14) . . ?
C3 C4 C5 118.23(13) . . ?
N2 C5 C4 108.68(11) . . ?
N2 C5 C8 109.42(11) . . ?
C4 C5 C8 112.21(11) . . ?
N2 C5 C6 102.47(10) . . ?
C4 C5 C6 116.04(11) . . ?
C8 C5 C6 107.48(10) . . ?
O2 C6 N1 110.49(11) . . ?
O2 C6 C5 111.97(11) . . ?
N1 C6 C5 102.45(10) . . ?
O1 C7 N1 126.22(13) . . ?
O1 C7 N2 125.77(12) . . ?
N1 C7 N2 108.00(11) . . ?
O3 C8 O4 125.78(13) . . ?
O3 C8 C5 124.03(12) . . ?
O4 C8 C5 110.16(11) . . ?
N1 C10 C11 112.92(11) . . ?
C16 C11 C12 119.30(16) . . ?
C16 C11 C10 121.06(15) . . ?
C12 C11 C10 119.63(14) . . ?
C13 C12 C11 120.40(19) . . ?
C14 C13 C12 120.3(2) . . ?
C13 C14 C15 120.16(19) . . ?
C14 C15 C16 120.5(2) . . ?
C11 C16 C15 119.3(2) . . ?

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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C7 N2 C1 C2 148.17(15) . . . . ?
C5 N2 C1 C2 -23.5(2) . . . . ?
N2 C1 C2 C3 -7.1(2) . . . . ?
C1 C2 C3 C4 15.6(2) . . . . ?
C2 C3 C4 C5 6.2(2) . . . . ?
C7 N2 C5 C4 -130.90(12) . . . . ?
C1 N2 C5 C4 41.82(17) . . . . ?
C7 N2 C5 C8 106.26(12) . . . . ?
C1 N2 C5 C8 -81.01(15) . . . . ?
C7 N2 C5 C6 -7.57(14) . . . . ?
C1 N2 C5 C6 165.15(12) . . . . ?
C3 C4 C5 N2 -32.31(18) . . . . ?
C3 C4 C5 C8 88.83(16) . . . . ?
C3 C4 C5 C6 -147.08(13) . . . . ?
C7 N1 C6 O2 -126.42(12) . . . . ?
C10 N1 C6 O2 50.63(16) . . . . ?
C7 N1 C6 C5 -6.98(14) . . . . ?
C10 N1 C6 C5 170.07(11) . . . . ?
N2 C5 C6 O2 126.59(11) . . . . ?
C4 C5 C6 O2 -115.17(13) . . . . ?
C8 C5 C6 O2 11.34(14) . . . . ?
N2 C5 C6 N1 8.20(13) . . . . ?
C4 C5 C6 N1 126.43(12) . . . . ?
C8 C5 C6 N1 -107.06(11) . . . . ?
C6 N1 C7 O1 -176.39(13) . . . . ?
C10 N1 C7 O1 6.6(2) . . . . ?
C6 N1 C7 N2 2.57(15) . . . . ?
C10 N1 C7 N2 -174.43(12) . . . . ?
C1 N2 C7 O1 10.4(2) . . . . ?
C5 N2 C7 O1 -177.42(13) . . . . ?
C1 N2 C7 N1 -168.59(13) . . . . ?
C5 N2 C7 N1 3.61(15) . . . . ?
C9 O4 C8 O3 -4.5(2) . . . . ?
C9 O4 C8 C5 173.55(12) . . . . ?
N2 C5 C8 O3 -22.16(18) . . . . ?
C4 C5 C8 O3 -142.87(14) . . . . ?
C6 C5 C8 O3 88.39(15) . . . . ?
N2 C5 C8 O4 159.74(11) . . . . ?
C4 C5 C8 O4 39.03(15) . . . . ?
C6 C5 C8 O4 -89.71(12) . . . . ?
C7 N1 C10 C11 -119.88(14) . . . . ?
C6 N1 C10 C11 63.37(17) . . . . ?
N1 C10 C11 C16 74.91(17) . . . . ?
N1 C10 C11 C12 -106.05(15) . . . . ?
C16 C11 C12 C13 0.9(2) . . . . ?
C10 C11 C12 C13 -178.14(14) . . . . ?
C11 C12 C13 C14 -0.4(3) . . . . ?
C12 C13 C14 C15 -0.3(3) . . . . ?
C13 C14 C15 C16 0.4(3) . . . . ?
C12 C11 C16 C15 -0.7(2) . . . . ?
C10 C11 C16 C15 178.30(15) . . . . ?
C14 C15 C16 C11 0.1(3) . . . . ?

_refine_diff_density_max         0.265
_refine_diff_density_min         -0.188
_refine_diff_density_rms         0.041



