# Supplementary Information (SI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 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_p20240809e
_database_code_depnum_ccdc_archive 'CCDC 2378637'
loop_
_audit_author_name
_audit_author_address
Ling
;NanKai University
China
;
_audit_update_record             
;
2024-08-20 deposited with the CCDC.	2025-04-15 downloaded from the CCDC.
;
_audit_creation_date             2024-08-13
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H15 N O4'
_chemical_formula_sum            'C14 H15 N O4'
_chemical_formula_weight         261.27
_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                   7.41048(5)
_cell_length_b                   6.29241(5)
_cell_length_c                   28.74880(18)
_cell_angle_alpha                90
_cell_angle_beta                 94.1631(6)
_cell_angle_gamma                90
_cell_volume                     1337.014(16)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    19269
_cell_measurement_temperature    143.15
_cell_measurement_theta_max      78.8460
_cell_measurement_theta_min      3.0740
_shelx_estimated_absorpt_T_max   0.890
_shelx_estimated_absorpt_T_min   0.832
_exptl_absorpt_coefficient_mu    0.795
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.01059
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.298
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0246
_diffrn_reflns_av_unetI/netI     0.0167
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            24793
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.155
_diffrn_reflns_theta_min         3.082
_diffrn_ambient_temperature      143.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -84.00  41.00   0.50    0.50    --  -48.80  35.00  55.00  250
  2  ω   -145.00 -21.00   0.50    0.50    -- -110.00  35.00  55.00  248
  3  ω   -199.00 -75.00   0.50    0.50    -- -110.00 -35.00-101.00  248
  4  ω    -84.00  35.00   0.50    0.50    --    5.00 -57.00-150.00  238
  5  ω   -138.00 -18.00   0.50    0.50    --  -48.80 -58.00 134.06  240
  6  ω   -138.00 -13.00   0.50    0.50    --  -48.80 -35.00-101.00  250
  7  ω    -79.00  41.00   0.50    0.50    --  -48.80  57.00-150.00  240
  8  ω   -138.00 -11.00   0.50    0.50    --  -48.80 -30.00 128.98  254
  9  ω   -140.00 -21.00   0.50    0.50    -- -110.00  57.00  60.00  238
 10  ω   -137.00 -39.00   0.50    0.50    -- -110.00  57.00 -90.00  196
 11  ω   -192.00-167.00   0.50    0.50    -- -110.00 -43.00  92.95   50
 12  ω   -128.00 -83.00   0.50    0.50    -- -110.00 -43.00  92.95   90
 13  ω   -111.00 -79.00   0.50    0.50    -- -110.00 -46.00-154.18   64
 14  ω   -198.00 -81.00   0.50    0.50    -- -110.00 -53.00  13.42  234
 15  ω   -198.00-150.00   0.50    0.50    -- -110.00 -62.00 160.07   96
 16  ω   -140.00 -22.00   0.50    0.50    -- -110.00  57.00-150.00  236
 17  ω   -102.00 -76.00   0.50    0.50    -- -110.00 -72.00 150.00   52
 18  ω   -102.00 -77.00   0.50    0.50    -- -110.00 -68.00-173.38   50
 19  ω   -101.00 -75.00   0.50    0.50    -- -110.00 -36.00 134.40   52
 20  ω   -164.00-138.00   0.50    0.50    -- -110.00 -59.00-162.59   52
 21  ω   -111.00 -80.00   0.50    0.50    -- -110.00 -59.00-162.59   62
 22  ω   -107.00 -81.00   0.50    0.50    -- -110.00 -61.00 148.94   52
 23  ω   -134.00-100.00   0.50    0.50    -- -110.00  38.00-150.00   68
 24  ω    -71.00 -21.00   0.50    0.50    -- -110.00  38.00-150.00  100
 25  ω   -185.00-159.00   0.50    0.50    -- -110.00 -46.00-154.18   52
 26  ω   -189.00-124.00   0.50    0.50    -- -110.00 -68.00-173.38  130
 27  ω   -145.00 -84.00   0.50    0.50    -- -110.00 -54.00-128.50  122
 28  ω    -50.00 -24.00   0.50    0.50    -- -110.00  57.00-120.00   52
 29  ω   -198.00-116.00   0.50    0.50    -- -110.00 -38.00   0.00  164
 30  ω   -108.00 -82.00   0.50    0.50    -- -110.00 -40.00 107.03   52
 31  ω   -106.00 -80.00   0.50    0.50    -- -110.00 -64.00 125.27   52
 32  ω   -140.00 -75.00   0.50    0.50    -- -110.00  57.00-120.00  130
 33  ω   -104.00 -79.00   0.50    0.50    -- -110.00 -62.00 160.07   50
 34  ω   -174.00 -75.00   0.50    0.50    -- -110.00 -36.00 145.84  198
 35  ω   -104.00 -77.00   0.50    0.50    -- -110.00 -38.00-180.00   54
 36  ω   -199.00-111.00   0.50    0.50    -- -110.00 -72.00 150.00  176
 37  ω   -175.00-146.00   0.50    0.50    -- -110.00 -42.00  99.12   58
 38  ω   -114.00 -78.00   0.50    0.50    -- -110.00 -42.00  99.12   72
 39  ω   -105.00 -79.00   0.50    0.50    -- -110.00 -70.00-159.18   52
 40  ω   -102.00 -75.00   0.50    0.50    -- -110.00 -36.00 119.22   54
 41  ω   -153.00-127.00   0.50    0.50    -- -110.00 -57.00-120.00   52
 42  ω   -109.00 -80.00   0.50    0.50    -- -110.00 -57.00-120.00   58
 43  ω   -105.00 -79.00   0.50    0.50    -- -110.00 -43.00 118.66   52
 44  ω   -104.00 -79.00   0.50    0.50    -- -110.00 -61.00 149.49   50
 45  ω   -119.00 -84.00   0.50    0.50    -- -110.00 -62.00  91.80   70
 46  ω   -103.00 -78.00   0.50    0.50    -- -110.00 -65.00 172.82   50
 47  ω   -109.00 -80.00   0.50    0.50    -- -110.00 -72.00 120.00   58
 48  ω   -114.00 -78.00   0.50    0.50    -- -110.00 -35.00 129.87   72
 49  ω   -106.00 -59.00   0.50    0.50    -- -110.00 -19.00 120.00   94
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0886055000
_diffrn_orient_matrix_UB_12      0.0998515000
_diffrn_orient_matrix_UB_13      0.0416374000
_diffrn_orient_matrix_UB_21      -0.1886225000
_diffrn_orient_matrix_UB_22      -0.0421986000
_diffrn_orient_matrix_UB_23      -0.0243832000
_diffrn_orient_matrix_UB_31      -0.0041496000
_diffrn_orient_matrix_UB_32      -0.2195596000
_diffrn_orient_matrix_UB_33      0.0236172000
_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         0.801
_reflns_Friedel_fraction_full    0.982
_reflns_Friedel_fraction_max     0.959
_reflns_number_gt                5490
_reflns_number_total             5663
_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 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_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         0.186
_refine_diff_density_min         -0.152
_refine_diff_density_rms         0.032
_refine_ls_abs_structure_details 
;
 Flack x determined using 2337 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.10(5)
_refine_ls_extinction_coef       0.0032(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.109
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     358
_refine_ls_number_reflns         5663
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0313
_refine_ls_R_factor_gt           0.0308
_refine_ls_restrained_S_all      1.109
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0592P)²+0.0773P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0913
_refine_ls_wR_factor_ref         0.0918
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 N1-H1 = N2-H2
 0.9 with sigma of 0.01
3.a Ternary CH refined with riding coordinates:
 C11(H11), C25(H25)
3.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C7(H7), C8(H8), C18(H18), C19(H19), C21(H21), C22(H22)
3.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C12(H12A,H12B,H12C), C14(H14A,H14B,H14C), C15(H15A,H15B,
 H15C), C26(H26A,H26B,H26C), C28(H28A,H28B,H28C)
;
_atom_sites_solution_hydrogens   mixed
_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 0.40117(18) 1.2124(2) 0.91026(4) 0.0436(3) Uani 1 1 d . . . . .
O2 O 0.5494(2) 0.9315(3) 0.94144(4) 0.0537(4) Uani 1 1 d . . . . .
O3 O 0.27598(15) 0.7578(2) 0.58657(4) 0.0370(3) Uani 1 1 d . . . . .
O4 O 0.54892(14) 0.71921(19) 0.55722(4) 0.0342(2) Uani 1 1 d . . . . .
N1 N 0.47004(16) 0.4968(2) 0.61200(4) 0.0286(3) Uani 1 1 d D . . . .
H1 H 0.575(2) 0.434(4) 0.6083(7) 0.040(5) Uiso 1 1 d D . . . .
C1 C 0.4258(3) 1.3182(4) 0.95500(6) 0.0513(5) Uani 1 1 d . . . . .
H1A H 0.370993 1.459948 0.952689 0.077 Uiso 1 1 calc R U . . .
H1B H 0.555344 1.331557 0.964063 0.077 Uiso 1 1 calc R U . . .
H1C H 0.367678 1.234845 0.978521 0.077 Uiso 1 1 calc R U . . .
C2 C 0.4719(2) 1.0180(3) 0.90866(5) 0.0330(3) Uani 1 1 d . . . . .
C3 C 0.4482(2) 0.9220(3) 0.86116(5) 0.0283(3) Uani 1 1 d . . . . .
C4 C 0.35613(19) 1.0272(3) 0.82371(5) 0.0318(3) Uani 1 1 d . . . . .
H4 H 0.303819 1.162735 0.828249 0.038 Uiso 1 1 calc R U . . .
C5 C 0.3413(2) 0.9338(3) 0.78013(5) 0.0326(3) Uani 1 1 d . . . . .
H5 H 0.277871 1.005340 0.754831 0.039 Uiso 1 1 calc R U . . .
C6 C 0.41881(19) 0.7350(3) 0.77291(5) 0.0288(3) Uani 1 1 d . . . . .
C7 C 0.5111(2) 0.6300(3) 0.81035(5) 0.0331(3) Uani 1 1 d . . . . .
H7 H 0.565106 0.495425 0.805783 0.040 Uiso 1 1 calc R U . . .
C8 C 0.5236(2) 0.7232(3) 0.85419(5) 0.0327(3) Uani 1 1 d . . . . .
H8 H 0.584224 0.650483 0.879719 0.039 Uiso 1 1 calc R U . . .
C9 C 0.4004(2) 0.6348(3) 0.72776(5) 0.0309(3) Uani 1 1 d . . . . .
C10 C 0.38202(19) 0.5438(3) 0.69108(5) 0.0302(3) Uani 1 1 d . . . . .
C11 C 0.35680(18) 0.4183(3) 0.64763(5) 0.0275(3) Uani 1 1 d . . . . .
H11 H 0.227394 0.430862 0.635440 0.033 Uiso 1 1 calc R U . . .
C12 C 0.3977(2) 0.1847(3) 0.65731(5) 0.0347(3) Uani 1 1 d . . . . .
H12A H 0.388839 0.105506 0.627879 0.052 Uiso 1 1 calc R U . . .
H12B H 0.310253 0.127644 0.678052 0.052 Uiso 1 1 calc R U . . .
H12C H 0.520268 0.170574 0.672222 0.052 Uiso 1 1 calc R U . . .
C13 C 0.41974(19) 0.6648(2) 0.58574(5) 0.0266(3) Uani 1 1 d . . . . .
C14 C 0.5047(2) 0.8963(3) 0.52666(6) 0.0405(4) Uani 1 1 d . . . . .
H14A H 0.411995 0.852927 0.502482 0.061 Uiso 1 1 calc R U . . .
H14B H 0.613444 0.942410 0.511991 0.061 Uiso 1 1 calc R U . . .
H14C H 0.458668 1.013996 0.544730 0.061 Uiso 1 1 calc R U . . .
O5 O 1.03262(17) 0.7167(2) 0.90936(4) 0.0432(3) Uani 1 1 d . . . . .
O6 O 0.9099(2) 0.4359(3) 0.94262(4) 0.0546(4) Uani 1 1 d . . . . .
O7 O 0.77666(15) 0.2567(2) 0.58726(4) 0.0372(3) Uani 1 1 d . . . . .
O8 O 1.04832(15) 0.2125(2) 0.55760(4) 0.0347(3) Uani 1 1 d . . . . .
N2 N 0.96781(16) -0.0077(2) 0.61267(4) 0.0290(3) Uani 1 1 d D . . . .
H2 H 1.074(2) -0.070(4) 0.6089(7) 0.040(5) Uiso 1 1 d D . . . .
C15 C 1.0401(3) 0.8238(3) 0.95399(6) 0.0500(5) Uani 1 1 d . . . . .
H15A H 1.084026 0.969400 0.950390 0.075 Uiso 1 1 calc R U . . .
H15B H 1.122481 0.747177 0.976313 0.075 Uiso 1 1 calc R U . . .
H15C H 0.918856 0.827519 0.965499 0.075 Uiso 1 1 calc R U . . .
C16 C 0.9624(2) 0.5216(3) 0.90893(5) 0.0326(3) Uani 1 1 d . . . . .
C17 C 0.9519(2) 0.4243(3) 0.86143(5) 0.0283(3) Uani 1 1 d . . . . .
C18 C 1.01526(19) 0.5287(3) 0.82308(5) 0.0312(3) Uani 1 1 d . . . . .
H18 H 1.070352 0.664535 0.826886 0.037 Uiso 1 1 calc R U . . .
C19 C 0.9980(2) 0.4346(3) 0.77939(5) 0.0320(3) Uani 1 1 d . . . . .
H19 H 1.042417 0.505471 0.753378 0.038 Uiso 1 1 calc R U . . .
C20 C 0.91524(19) 0.2353(3) 0.77346(5) 0.0283(3) Uani 1 1 d . . . . .
C21 C 0.8529(2) 0.1305(3) 0.81207(5) 0.0330(3) Uani 1 1 d . . . . .
H21 H 0.797585 -0.005252 0.808412 0.040 Uiso 1 1 calc R U . . .
C22 C 0.8721(2) 0.2250(3) 0.85568(5) 0.0327(3) Uani 1 1 d . . . . .
H22 H 0.830311 0.153024 0.881896 0.039 Uiso 1 1 calc R U . . .
C23 C 0.8962(2) 0.1350(3) 0.72838(5) 0.0303(3) Uani 1 1 d . . . . .
C24 C 0.87943(19) 0.0434(3) 0.69169(5) 0.0299(3) Uani 1 1 d . . . . .
C25 C 0.85465(18) -0.0837(3) 0.64850(5) 0.0276(3) Uani 1 1 d . . . . .
H25 H 0.725246 -0.071938 0.636251 0.033 Uiso 1 1 calc R U . . .
C26 C 0.8959(2) -0.3167(3) 0.65874(5) 0.0340(3) Uani 1 1 d . . . . .
H26A H 0.877309 -0.399284 0.629891 0.051 Uiso 1 1 calc R U . . .
H26B H 0.815149 -0.369596 0.681653 0.051 Uiso 1 1 calc R U . . .
H26C H 1.021877 -0.331161 0.671262 0.051 Uiso 1 1 calc R U . . .
C27 C 0.91905(19) 0.1610(2) 0.58633(5) 0.0270(3) Uani 1 1 d . . . . .
C28 C 1.0058(3) 0.3894(3) 0.52689(6) 0.0413(4) Uani 1 1 d . . . . .
H28A H 0.911630 0.347172 0.502978 0.062 Uiso 1 1 calc R U . . .
H28B H 1.114606 0.432586 0.511898 0.062 Uiso 1 1 calc R U . . .
H28C H 0.962217 0.508657 0.544916 0.062 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
O1 C1 1.4479(19) . ?
O1 C2 1.333(2) . ?
O2 C2 1.198(2) . ?
O3 C13 1.2171(19) . ?
O4 C13 1.3490(19) . ?
O4 C14 1.442(2) . ?
N1 H1 0.883(12) . ?
N1 C11 1.4569(19) . ?
N1 C13 1.336(2) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 C3 1.4920(19) . ?
C3 C4 1.398(2) . ?
C3 C8 1.390(2) . ?
C4 H4 0.9500 . ?
C4 C5 1.381(2) . ?
C5 H5 0.9500 . ?
C5 C6 1.399(2) . ?
C6 C7 1.398(2) . ?
C6 C9 1.440(2) . ?
C7 H7 0.9500 . ?
C7 C8 1.387(2) . ?
C8 H8 0.9500 . ?
C9 C10 1.199(2) . ?
C10 C11 1.4778(19) . ?
C11 H11 1.0000 . ?
C11 C12 1.522(2) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
O5 C15 1.4468(19) . ?
O5 C16 1.334(2) . ?
O6 C16 1.198(2) . ?
O7 C27 1.2169(19) . ?
O8 C27 1.3490(19) . ?
O8 C28 1.441(2) . ?
N2 H2 0.894(12) . ?
N2 C25 1.4554(19) . ?
N2 C27 1.338(2) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 C17 1.4933(19) . ?
C17 C18 1.394(2) . ?
C17 C22 1.392(2) . ?
C18 H18 0.9500 . ?
C18 C19 1.386(2) . ?
C19 H19 0.9500 . ?
C19 C20 1.401(2) . ?
C20 C21 1.398(2) . ?
C20 C23 1.439(2) . ?
C21 H21 0.9500 . ?
C21 C22 1.386(2) . ?
C22 H22 0.9500 . ?
C23 C24 1.201(2) . ?
C24 C25 1.4770(19) . ?
C25 H25 1.0000 . ?
C25 C26 1.522(2) . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?

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 O1 C1 115.35(14) . . ?
C13 O4 C14 115.25(12) . . ?
C11 N1 H1 119.1(15) . . ?
C13 N1 H1 119.9(15) . . ?
C13 N1 C11 120.95(12) . . ?
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O1 C2 C3 112.51(13) . . ?
O2 C2 O1 123.86(16) . . ?
O2 C2 C3 123.61(17) . . ?
C4 C3 C2 122.11(14) . . ?
C8 C3 C2 118.33(13) . . ?
C8 C3 C4 119.55(14) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 C3 119.99(15) . . ?
C5 C4 H4 120.0 . . ?
C4 C5 H5 119.7 . . ?
C4 C5 C6 120.57(14) . . ?
C6 C5 H5 119.7 . . ?
C5 C6 C9 120.81(14) . . ?
C7 C6 C5 119.42(14) . . ?
C7 C6 C9 119.75(14) . . ?
C6 C7 H7 120.1 . . ?
C8 C7 C6 119.76(14) . . ?
C8 C7 H7 120.1 . . ?
C3 C8 H8 119.7 . . ?
C7 C8 C3 120.70(14) . . ?
C7 C8 H8 119.7 . . ?
C10 C9 C6 177.15(18) . . ?
C9 C10 C11 176.12(18) . . ?
N1 C11 C10 111.67(13) . . ?
N1 C11 H11 108.3 . . ?
N1 C11 C12 109.81(12) . . ?
C10 C11 H11 108.3 . . ?
C10 C11 C12 110.49(13) . . ?
C12 C11 H11 108.3 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
O3 C13 O4 123.41(14) . . ?
O3 C13 N1 125.30(15) . . ?
N1 C13 O4 111.28(12) . . ?
O4 C14 H14A 109.5 . . ?
O4 C14 H14B 109.5 . . ?
O4 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C16 O5 C15 115.27(14) . . ?
C27 O8 C28 115.29(13) . . ?
C25 N2 H2 120.1(15) . . ?
C27 N2 H2 118.8(15) . . ?
C27 N2 C25 121.02(12) . . ?
O5 C15 H15A 109.5 . . ?
O5 C15 H15B 109.5 . . ?
O5 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
O5 C16 C17 112.34(13) . . ?
O6 C16 O5 123.82(16) . . ?
O6 C16 C17 123.82(16) . . ?
C18 C17 C16 122.15(15) . . ?
C22 C17 C16 118.13(13) . . ?
C22 C17 C18 119.70(14) . . ?
C17 C18 H18 120.0 . . ?
C19 C18 C17 120.07(15) . . ?
C19 C18 H18 120.0 . . ?
C18 C19 H19 119.9 . . ?
C18 C19 C20 120.25(14) . . ?
C20 C19 H19 119.9 . . ?
C19 C20 C23 121.04(14) . . ?
C21 C20 C19 119.50(13) . . ?
C21 C20 C23 119.45(15) . . ?
C20 C21 H21 120.1 . . ?
C22 C21 C20 119.86(15) . . ?
C22 C21 H21 120.1 . . ?
C17 C22 H22 119.7 . . ?
C21 C22 C17 120.60(13) . . ?
C21 C22 H22 119.7 . . ?
C24 C23 C20 177.27(18) . . ?
C23 C24 C25 175.67(18) . . ?
N2 C25 C24 111.97(13) . . ?
N2 C25 H25 108.3 . . ?
N2 C25 C26 109.59(12) . . ?
C24 C25 H25 108.3 . . ?
C24 C25 C26 110.36(13) . . ?
C26 C25 H25 108.3 . . ?
C25 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
C25 C26 H26C 109.5 . . ?
H26A C26 H26B 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
O7 C27 O8 123.37(15) . . ?
O7 C27 N2 125.38(15) . . ?
N2 C27 O8 111.25(12) . . ?
O8 C28 H28A 109.5 . . ?
O8 C28 H28B 109.5 . . ?
O8 C28 H28C 109.5 . . ?
H28A C28 H28B 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?

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 C2 C3 C4 -1.8(2) . . . . ?
O1 C2 C3 C8 176.98(15) . . . . ?
O2 C2 C3 C4 179.69(18) . . . . ?
O2 C2 C3 C8 -1.5(2) . . . . ?
C1 O1 C2 O2 0.8(3) . . . . ?
C1 O1 C2 C3 -177.66(15) . . . . ?
C2 C3 C4 C5 178.52(14) . . . . ?
C2 C3 C8 C7 -177.70(14) . . . . ?
C3 C4 C5 C6 -0.5(2) . . . . ?
C4 C3 C8 C7 1.1(2) . . . . ?
C4 C5 C6 C7 0.4(2) . . . . ?
C4 C5 C6 C9 178.64(14) . . . . ?
C5 C6 C7 C8 0.5(2) . . . . ?
C6 C7 C8 C3 -1.3(2) . . . . ?
C8 C3 C4 C5 -0.3(2) . . . . ?
C9 C6 C7 C8 -177.80(14) . . . . ?
C11 N1 C13 O3 -4.7(2) . . . . ?
C11 N1 C13 O4 175.95(12) . . . . ?
C13 N1 C11 C10 -81.20(16) . . . . ?
C13 N1 C11 C12 155.89(13) . . . . ?
C14 O4 C13 O3 -0.8(2) . . . . ?
C14 O4 C13 N1 178.58(13) . . . . ?
O5 C16 C17 C18 1.9(2) . . . . ?
O5 C16 C17 C22 -176.61(15) . . . . ?
O6 C16 C17 C18 -179.69(18) . . . . ?
O6 C16 C17 C22 1.8(2) . . . . ?
C15 O5 C16 O6 -0.8(3) . . . . ?
C15 O5 C16 C17 177.64(15) . . . . ?
C16 C17 C18 C19 -178.17(13) . . . . ?
C16 C17 C22 C21 177.70(14) . . . . ?
C17 C18 C19 C20 0.6(2) . . . . ?
C18 C17 C22 C21 -0.8(2) . . . . ?
C18 C19 C20 C21 -1.1(2) . . . . ?
C18 C19 C20 C23 -179.94(14) . . . . ?
C19 C20 C21 C22 0.5(2) . . . . ?
C20 C21 C22 C17 0.4(2) . . . . ?
C22 C17 C18 C19 0.3(2) . . . . ?
C23 C20 C21 C22 179.44(14) . . . . ?
C25 N2 C27 O7 -4.7(2) . . . . ?
C25 N2 C27 O8 175.94(12) . . . . ?
C27 N2 C25 C24 -80.26(16) . . . . ?
C27 N2 C25 C26 156.93(13) . . . . ?
C28 O8 C27 O7 -0.9(2) . . . . ?
C28 O8 C27 N2 178.42(13) . . . . ?

_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 63.430
_oxdiff_exptl_absorpt_empirical_full_min 0.580
