# Supplementary Information (SI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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_tianjinrui-tyq_1113_auto
_database_code_depnum_ccdc_archive 'CCDC 2362885'
loop_
_audit_author_name
_audit_author_address
Tianjinrui
;LanZhou University
China
;
_audit_update_record             
;
2024-06-14 deposited with the CCDC.	2024-08-11 downloaded from the CCDC.
;
_audit_creation_date             2024-01-11
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C13 H15 N O4'
_chemical_formula_sum            'C13 H15 N O4'
_chemical_formula_weight         249.26
_chemical_absolute_configuration ad
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   7.5054(2)
_cell_length_b                   10.0086(2)
_cell_length_c                   8.5104(2)
_cell_angle_alpha                90
_cell_angle_beta                 110.518(2)
_cell_angle_gamma                90
_cell_volume                     598.73(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    6934
_cell_measurement_temperature    302.44(10)
_cell_measurement_theta_max      75.8580
_cell_measurement_theta_min      4.4370
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.858
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.67466
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.93a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.383
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             264
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0256
_diffrn_reflns_av_unetI/netI     0.0183
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.964
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            7782
_diffrn_reflns_point_group_measured_fraction_full 0.946
_diffrn_reflns_point_group_measured_fraction_max 0.900
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.996
_diffrn_reflns_theta_min         5.550
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      302.44(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.964
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     57.00 100.00   0.50    0.05    --  104.27 -94.00   0.00   86
  2  ω     36.00  93.00   0.50    0.05    --  104.27 -94.00 -30.00  114
  3  ω     35.00  73.00   0.50    0.05    --  104.27 -94.00 -60.00   76
  4  ω     78.00 104.00   0.50    0.05    --  104.27 -94.00-120.00   52
  5  ω     34.00  59.00   0.50    0.05    --  104.27 -94.00-120.00   50
  6  ω    -25.00   0.00   0.50    0.05    --   46.54 -13.00  97.00   50
  7  ω   -121.00 -60.00   0.50    0.05    --  -46.54 -13.00  97.00  122
  8  ω   -111.00 -79.00   0.50    0.05    -- -102.00 -77.00 -30.00   64
  9  ω   -163.00-138.00   0.50    0.05    -- -102.00 -77.00  90.00   50
 10  ω   -173.00-127.00   0.50    0.05    -- -102.00 -77.00 120.00   92
 11  ω   -160.00-135.00   0.50    0.05    -- -102.00 -77.00 -30.00   50
 12  ω   -104.00 -79.00   0.50    0.05    -- -102.00 -77.00   0.00   50
 13  ω   -107.00 -79.00   0.50    0.05    -- -102.00 -77.00  30.00   56
 14  ω   -118.00 -82.00   0.50    0.05    -- -102.00 -71.00  48.88   72
 15  ω   -105.00 -79.00   0.50    0.05    -- -102.00 -76.00  64.45   52
 16  ω   -105.00 -80.00   0.50    0.05    -- -102.00 -77.00  90.00   50
 17  ω   -154.00-123.00   0.50    0.05    -- -102.00 -68.00 -57.45   62
 18  ω   -109.00 -84.00   0.50    0.05    -- -102.00 -64.00 -31.78   50
 19  ω   -115.00 -84.00   0.50    0.05    -- -102.00 -68.00 -57.45   62
 20  ω   -168.00 -86.00   0.50    0.05    -- -102.00 -64.00  30.30  164
 21  ω   -120.00 -86.00   0.50    0.05    -- -102.00 -61.00   0.00   68
 22  ω   -112.00 -87.00   0.50    0.05    -- -102.00 -61.00 -30.00   50
 23  ω   -111.00 -86.00   0.50    0.05    -- -102.00 -60.00  -5.81   50
 24  ω   -166.00-140.00   0.50    0.05    -- -102.00 -60.00  -5.81   52
 25  ω   -126.00 -86.00   0.50    0.05    -- -102.00 -59.00 -16.35   80
 26  ω   -110.00 -85.00   0.50    0.05    -- -102.00 -61.00  60.00   50
 27  ω   -170.00-124.00   0.50    0.05    -- -102.00 -47.00  40.11   92
 28  ω   -172.00-146.00   0.50    0.05    -- -102.00 -59.00 -16.35   52
 29  ω   -118.00 -93.00   0.50    0.05    -- -102.00 -47.00  40.11   50
 30  ω   -133.00-108.00   0.50    0.05    -- -102.00 -13.00  97.00   50
 31  ω   -139.00 -90.00   0.50    0.05    -- -102.00 -45.00  60.00   98
 32  ω    -81.00 -34.00   0.50    0.05    --  -46.54 -19.00   0.00   94
 33  ω   -121.00 -91.00   0.50    0.05    -- -102.00 -30.00 -60.00   60
 34  ω    -87.00 -14.00   0.50    0.05    --  -46.54 125.00  60.00  146
 35  ω    -64.00 -29.00   0.50    0.05    -- -102.00  61.00  60.00   70
 36  ω    -68.00 -29.00   0.50    0.05    -- -102.00  61.00  90.00   78
 37  ω    -69.00 -32.00   0.50    0.05    -- -102.00  61.00  30.00   74
 38  ω    -67.00 -30.00   0.50    0.05    -- -102.00  61.00-180.00   74
 39  ω    -21.00   4.00   0.50    0.05    --  -46.54  13.00 -90.00   50
 40  ω      2.00  27.00   0.50    0.05    --  -46.54  19.00 -30.00   50
 41  ω     88.00 119.00   0.50    0.05    --   46.54  77.00  30.00   62
 42  ω     74.00 100.00   0.50    0.05    --   46.54  77.00   0.00   52
 43  ω     25.00  81.00   0.50    0.05    --   46.54  77.00  30.00  112
 44  ω     26.00  64.00   0.50    0.05    --   46.54  77.00   0.00   76
 45  ω     25.00  58.00   0.50    0.05    --   46.54  77.00 -60.00   66
 46  ω     36.00  76.00   0.50    0.05    --   46.54  37.00   0.00   80
 47  ω     34.00  59.00   0.50    0.05    --   46.54  57.00 -30.00   50
 48  ω     43.00  79.00   0.50    0.05    --   46.54  13.00 -90.00   72
 49  ω     86.00 117.00   0.50    0.05    --  104.27  77.00 -90.00   62
 50  ω     85.00 111.00   0.50    0.05    --  104.27  77.00 -30.00   52
 51  ω     82.00 108.00   0.50    0.05    --  104.27  77.00   0.00   52
 52  ω    149.00 174.00   0.50    0.05    --  104.27  77.00 -30.00   50
 53  ω     88.00 166.00   0.50    0.05    --  104.27  61.00 -90.00  156
 54  ω     99.00 134.00   0.50    0.05    --  104.27  13.00 -90.00   70
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.2154637000
_diffrn_orient_matrix_UB_12      0.0279377000
_diffrn_orient_matrix_UB_13      -0.0622318000
_diffrn_orient_matrix_UB_21      0.0064282000
_diffrn_orient_matrix_UB_22      0.0039050000
_diffrn_orient_matrix_UB_23      0.1829133000
_diffrn_orient_matrix_UB_31      0.0395833000
_diffrn_orient_matrix_UB_32      0.1512781000
_diffrn_orient_matrix_UB_33      0.0065911000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.761
_reflns_Friedel_fraction_full    0.894
_reflns_Friedel_fraction_max     0.827
_reflns_number_gt                2200
_reflns_number_total             2258
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.93a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.93a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.93a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.194
_refine_diff_density_min         -0.145
_refine_diff_density_rms         0.036
_refine_ls_abs_structure_details 
;
 Flack x determined using 927 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.06(6)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     165
_refine_ls_number_reflns         2258
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0323
_refine_ls_R_factor_gt           0.0316
_refine_ls_restrained_S_all      1.066
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0518P)²+0.0442P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0822
_refine_ls_wR_factor_ref         0.0832
_refine_special_details          ?
_olex2_refinement_description    
;
1.a Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B), C7(H7A,H7B), C9(H9A,H9B), C11(H11A,H11B)
1.b Aromatic/amide H refined with riding coordinates:
 C1(H1A)
1.c Idealised Me refined as rotating group:
 C5(H5A,H5B,H5C)
1.d Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
O1 O 0.6102(2) 0.52055(16) 0.32844(16) 0.0493(4) Uani 1 1 d . . . . .
H1 H 0.573319 0.493791 0.231222 0.074 Uiso 1 1 calc R U . . .
O2 O 0.5288(2) 0.46172(19) 0.98890(18) 0.0608(5) Uani 1 1 d . . . . .
O3 O 0.2370(3) 0.4574(3) 0.2272(2) 0.0755(6) Uani 1 1 d . . . . .
O4 O 0.24738(19) 0.40139(18) 0.47787(18) 0.0518(4) Uani 1 1 d . . . . .
N1 N 0.7680(2) 0.56792(16) 0.92992(18) 0.0388(4) Uani 1 1 d . . . . .
C1 C 0.8014(3) 0.5564(2) 0.6645(2) 0.0380(4) Uani 1 1 d . . . . .
H1A H 0.866467 0.577841 0.592864 0.046 Uiso 1 1 calc R U . . .
C2 C 0.8501(4) 0.6299(3) 1.0967(2) 0.0539(6) Uani 1 1 d . . . . .
H2A H 0.913621 0.564000 1.181436 0.065 Uiso 1 1 calc R U . . .
H2B H 0.752973 0.674422 1.128484 0.065 Uiso 1 1 calc R U . . .
C3 C 0.9915(4) 0.7299(3) 1.0733(3) 0.0672(7) Uani 1 1 d . . . . .
H3A H 0.936591 0.818808 1.053897 0.081 Uiso 1 1 calc R U . . .
H3B H 1.106363 0.732231 1.171899 0.081 Uiso 1 1 calc R U . . .
C4 C 0.6339(3) 0.47874(17) 0.6081(2) 0.0329(4) Uani 1 1 d . . . . .
C5 C 0.8196(4) 0.2672(3) 0.4504(3) 0.0620(7) Uani 1 1 d . . . . .
H5A H 0.863218 0.327424 0.383756 0.093 Uiso 1 1 calc R U . . .
H5B H 0.844349 0.176868 0.426283 0.093 Uiso 1 1 calc R U . . .
H5C H 0.885431 0.285579 0.567183 0.093 Uiso 1 1 calc R U . . .
C6 C 0.6072(3) 0.4889(2) 0.8864(2) 0.0400(4) Uani 1 1 d . . . . .
C7 C 0.6084(3) 0.2859(2) 0.4094(3) 0.0479(5) Uani 1 1 d . . . . .
H7A H 0.567525 0.229434 0.482935 0.058 Uiso 1 1 calc R U . . .
H7B H 0.542097 0.256622 0.295043 0.058 Uiso 1 1 calc R U . . .
C8 C 0.5507(3) 0.4317(2) 0.4275(2) 0.0357(4) Uani 1 1 d . . . . .
C9 C 0.3580(3) 0.3694(2) 0.6510(2) 0.0459(5) Uani 1 1 d . . . . .
H9A H 0.385989 0.274471 0.660235 0.055 Uiso 1 1 calc R U . . .
H9B H 0.283209 0.389273 0.720832 0.055 Uiso 1 1 calc R U . . .
C10 C 0.8649(3) 0.59903(19) 0.8259(2) 0.0391(4) Uani 1 1 d . . . . .
C11 C 1.0353(3) 0.6819(3) 0.9215(2) 0.0558(6) Uani 1 1 d . . . . .
H11A H 1.050072 0.756629 0.854621 0.067 Uiso 1 1 calc R U . . .
H11B H 1.150517 0.628519 0.955353 0.067 Uiso 1 1 calc R U . . .
C12 C 0.5401(3) 0.44606(19) 0.7138(2) 0.0357(4) Uani 1 1 d . . . . .
C13 C 0.3329(3) 0.4327(2) 0.3698(2) 0.0458(5) 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
O1 H1 0.8200 . ?
O1 C8 1.402(2) . ?
O2 C6 1.242(2) . ?
O3 C13 1.200(3) . ?
O4 C9 1.451(3) . ?
O4 C13 1.331(2) . ?
N1 C2 1.472(2) . ?
N1 C6 1.380(2) . ?
N1 C10 1.364(2) . ?
C1 H1A 0.9300 . ?
C1 C4 1.412(2) . ?
C1 C10 1.355(3) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 C3 1.522(3) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 C11 1.518(3) . ?
C4 C8 1.517(2) . ?
C4 C12 1.362(2) . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C5 C7 1.510(3) . ?
C6 C12 1.441(2) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C7 C8 1.545(3) . ?
C8 C13 1.533(3) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 C12 1.494(3) . ?
C10 C11 1.502(3) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?

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 O1 H1 109.5 . . ?
C13 O4 C9 120.75(14) . . ?
C6 N1 C2 122.10(16) . . ?
C10 N1 C2 113.06(16) . . ?
C10 N1 C6 124.84(15) . . ?
C4 C1 H1A 120.9 . . ?
C10 C1 H1A 120.9 . . ?
C10 C1 C4 118.22(16) . . ?
N1 C2 H2A 111.2 . . ?
N1 C2 H2B 111.2 . . ?
N1 C2 C3 103.07(16) . . ?
H2A C2 H2B 109.1 . . ?
C3 C2 H2A 111.2 . . ?
C3 C2 H2B 111.2 . . ?
C2 C3 H3A 110.6 . . ?
C2 C3 H3B 110.6 . . ?
H3A C3 H3B 108.7 . . ?
C11 C3 C2 105.8(2) . . ?
C11 C3 H3A 110.6 . . ?
C11 C3 H3B 110.6 . . ?
C1 C4 C8 121.13(15) . . ?
C12 C4 C1 120.83(16) . . ?
C12 C4 C8 118.02(15) . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C7 C5 H5A 109.5 . . ?
C7 C5 H5B 109.5 . . ?
C7 C5 H5C 109.5 . . ?
O2 C6 N1 121.47(17) . . ?
O2 C6 C12 124.66(17) . . ?
N1 C6 C12 113.85(15) . . ?
C5 C7 H7A 108.8 . . ?
C5 C7 H7B 108.8 . . ?
C5 C7 C8 113.72(19) . . ?
H7A C7 H7B 107.7 . . ?
C8 C7 H7A 108.8 . . ?
C8 C7 H7B 108.8 . . ?
O1 C8 C4 107.90(14) . . ?
O1 C8 C7 112.30(15) . . ?
O1 C8 C13 109.36(16) . . ?
C4 C8 C7 111.37(16) . . ?
C4 C8 C13 109.68(14) . . ?
C13 C8 C7 106.21(16) . . ?
O4 C9 H9A 109.2 . . ?
O4 C9 H9B 109.2 . . ?
O4 C9 C12 112.06(16) . . ?
H9A C9 H9B 107.9 . . ?
C12 C9 H9A 109.2 . . ?
C12 C9 H9B 109.2 . . ?
N1 C10 C11 108.70(16) . . ?
C1 C10 N1 120.53(17) . . ?
C1 C10 C11 130.77(18) . . ?
C3 C11 H11A 111.0 . . ?
C3 C11 H11B 111.0 . . ?
C10 C11 C3 103.80(18) . . ?
C10 C11 H11A 111.0 . . ?
C10 C11 H11B 111.0 . . ?
H11A C11 H11B 109.0 . . ?
C4 C12 C6 121.65(16) . . ?
C4 C12 C9 120.49(16) . . ?
C6 C12 C9 117.80(15) . . ?
O3 C13 O4 118.92(19) . . ?
O3 C13 C8 121.35(19) . . ?
O4 C13 C8 119.70(16) . . ?

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
O1 C8 C13 O3 28.7(3) . . . . ?
O1 C8 C13 O4 -153.50(19) . . . . ?
O2 C6 C12 C4 -179.5(2) . . . . ?
O2 C6 C12 C9 3.3(3) . . . . ?
O4 C9 C12 C4 -33.0(3) . . . . ?
O4 C9 C12 C6 144.25(17) . . . . ?
N1 C2 C3 C11 -21.3(3) . . . . ?
N1 C6 C12 C4 2.0(3) . . . . ?
N1 C6 C12 C9 -175.15(18) . . . . ?
N1 C10 C11 C3 -16.9(3) . . . . ?
C1 C4 C8 O1 -25.1(2) . . . . ?
C1 C4 C8 C7 98.5(2) . . . . ?
C1 C4 C8 C13 -144.18(18) . . . . ?
C1 C4 C12 C6 0.0(3) . . . . ?
C1 C4 C12 C9 177.05(18) . . . . ?
C1 C10 C11 C3 162.6(2) . . . . ?
C2 N1 C6 O2 -3.1(3) . . . . ?
C2 N1 C6 C12 175.36(19) . . . . ?
C2 N1 C10 C1 -176.1(2) . . . . ?
C2 N1 C10 C11 3.5(3) . . . . ?
C2 C3 C11 C10 23.5(3) . . . . ?
C4 C1 C10 N1 -0.4(3) . . . . ?
C4 C1 C10 C11 -179.9(2) . . . . ?
C4 C8 C13 O3 146.9(2) . . . . ?
C4 C8 C13 O4 -35.4(3) . . . . ?
C5 C7 C8 O1 56.7(2) . . . . ?
C5 C7 C8 C4 -64.4(2) . . . . ?
C5 C7 C8 C13 176.23(18) . . . . ?
C6 N1 C2 C3 -167.5(2) . . . . ?
C6 N1 C10 C1 2.7(3) . . . . ?
C6 N1 C10 C11 -177.6(2) . . . . ?
C7 C8 C13 O3 -92.7(3) . . . . ?
C7 C8 C13 O4 85.1(2) . . . . ?
C8 C4 C12 C6 -178.77(16) . . . . ?
C8 C4 C12 C9 -1.7(3) . . . . ?
C9 O4 C13 O3 179.3(2) . . . . ?
C9 O4 C13 C8 1.5(3) . . . . ?
C10 N1 C2 C3 11.4(3) . . . . ?
C10 N1 C6 O2 178.1(2) . . . . ?
C10 N1 C6 C12 -3.4(3) . . . . ?
C10 C1 C4 C8 177.85(18) . . . . ?
C10 C1 C4 C12 -0.8(3) . . . . ?
C12 C4 C8 O1 153.58(17) . . . . ?
C12 C4 C8 C7 -82.7(2) . . . . ?
C12 C4 C8 C13 34.5(2) . . . . ?
C13 O4 C9 C12 32.9(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.435
_oxdiff_exptl_absorpt_empirical_full_min 0.617
