# Supplementary Information (SI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2026

####################################################################### 
# 
# 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_jds240053_fa_I
_database_code_depnum_ccdc_archive 'CCDC 2514195'
loop_
_audit_author_name
_audit_author_address
'Paul Waddell'
;Newcastle University
United Kingdom
;
_audit_update_record             
;
2025-12-08 deposited with the CCDC.	2026-02-09 downloaded from the CCDC.
;
_audit_creation_date             2024-08-21
_audit_creation_method           
;
Olex2 1.5-ac5-023
(compiled 2022.04.12 svn.rca3783a0 for Rigaku Oxford Diffraction, GUI svn.r6498)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H22 N2 O4'
_chemical_formula_sum            'C22 H22 N2 O4'
_chemical_formula_weight         378.41
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C11 H11 N1 O2'
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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   5.9187(2)
_cell_length_b                   8.0533(3)
_cell_length_c                   10.5862(3)
_cell_angle_alpha                99.782(3)
_cell_angle_beta                 96.732(3)
_cell_angle_gamma                102.517(3)
_cell_volume                     479.17(3)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    4199
_cell_measurement_temperature    150.0(2)
_cell_measurement_theta_max      75.1720
_cell_measurement_theta_min      4.2870
_shelx_estimated_absorpt_T_max   0.936
_shelx_estimated_absorpt_T_min   0.860
_exptl_absorpt_coefficient_mu    0.742
_exptl_absorpt_correction_T_max  0.952
_exptl_absorpt_correction_T_min  0.910
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.126a (Rigaku Oxford Diffraction, 2024)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.311
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             200
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 -1 -1 0.0583
-1 1 1 0.0563
0 0 -1 0.0485
0 0 1 0.0375
0 1 0 0.0566
0 -1 0 0.0626
-1 1 -1 0.0462
1 -1 1 0.0462
0 1 1 0.0477
0 -1 -1 0.0477
1 -2 -1 0.0524
-1 2 1 0.0494
1 0 0 0.0822
-1 0 0 0.0822
-1 2 -1 0.0543

_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.09
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
1.0000 -1.0000 -1.0000 0.3241 -0.0373 0.0434
-1.0000 1.0000 1.0000 -0.3241 0.0373 -0.0434
-0.0000 0.0000 -1.0000 0.0793 0.1251 0.0212
0.0000 -0.0000 1.0000 -0.0793 -0.1251 -0.0212
0.0000 1.0000 0.0000 -0.1226 0.0027 0.1581
-0.0000 -1.0000 -0.0000 0.1226 -0.0027 -0.1581
-1.0000 1.0000 -1.0000 -0.1656 0.2875 -0.0009
1.0000 -1.0000 1.0000 0.1656 -0.2875 0.0009
0.0000 1.0000 1.0000 -0.2019 -0.1224 0.1368
-0.0000 -1.0000 -1.0000 0.2019 0.1224 -0.1368
1.0000 -2.0000 -1.0000 0.4468 -0.0400 -0.1147
-1.0000 2.0000 1.0000 -0.4468 0.0400 0.1147
1.0000 -0.0000 0.0000 0.1223 -0.1598 0.1802
-1.0000 0.0000 -0.0000 -0.1223 0.1598 -0.1802
-1.0000 2.0000 -1.0000 -0.2883 0.2902 0.1571

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0282
_diffrn_reflns_av_unetI/netI     0.0200
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.931
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            9088
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.931
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.316
_diffrn_reflns_theta_min         4.293
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.0(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            'HyPix-Arc 100'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.931
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -51.00 -11.00   0.50    0.05    --  -92.45  45.00-120.00   80
  2  ω    -51.00 -11.00   0.50    0.05    --  -92.45  45.00  30.00   80
  3  ω    -51.00 -11.00   0.50    0.05    --  -92.45  45.00 150.00   80
  4  ω    -26.00  35.00   0.50    0.05    --  -47.30  19.00  60.00  122
  5  ω     15.00 117.00   0.50    0.05    --   46.55  77.00  90.00  204
  6  ω     15.00 117.00   0.50    0.05    --   46.55  77.00   0.00  204
  7  ω     15.00  95.00   0.50    0.05    --   46.55  77.00-150.00  160
  8  ω     20.00 175.00   0.50    0.05    --   97.16   0.00-150.00  310
  9  ω     78.00 178.00   0.50    0.05    --  108.12 118.00 -78.00  200
 10  ω     51.00 115.00   0.50    0.05    --   46.55 161.00  72.00  128
 11  ω     50.00 157.00   0.50    0.05    --  108.12 161.00  72.00  214
 12  ω     31.00  71.00   0.50    0.05    --  108.12 -61.00  90.00   80
 13  ω     27.00 105.00   0.50    0.05    --   97.16 -77.00   0.00  156
 14  ω     27.00 105.00   0.50    0.05    --   97.16 -77.00   0.00  156
 15  ω     31.00  71.00   0.50    0.05    --  108.12 -61.00  60.00   80
 16  ω     31.00  71.00   0.50    0.05    --  108.12 -61.00   0.00   80
 17  ω     38.00 105.00   0.50    0.05    --  108.12 -77.00-150.00  134
 18  ω     16.00  51.00   0.50    0.05    --   97.16 -45.00-150.00   70
 19  ω     20.00  71.00   0.50    0.05    --   97.16 -61.00-180.00  102
 20  ω     22.00 109.00   0.50    0.05    --   97.16-118.00-165.00  174
 21  ω     35.00 105.00   0.50    0.05    --  108.12 -95.00   0.00  140
 22  ω     35.00 105.00   0.50    0.05    --  108.12 -95.00  90.00  140
 23  ω     35.00 105.00   0.50    0.05    --  108.12 -95.00  90.00  140
 24  ω   -130.00 -31.00   0.50    0.05    --  -47.30 161.00  72.00  198
 25  ω   -101.00  -8.00   0.50    0.05    --  -47.30 118.00 -78.00  186
 26  ω   -109.00 -17.00   0.50    0.05    --  -92.45 118.00 -78.00  184
 27  ω   -175.00 -23.00   0.50    0.05    --  -92.45 -15.00-150.00  304
 28  ω   -175.00 -23.00   0.50    0.05    --  -92.45 -15.00-150.00  304
 29  ω   -175.00 -23.00   0.50    0.05    --  -92.45 -15.00-150.00  304
 30  ω   -169.00 -67.00   0.50    0.05    --  -92.45 -61.00 -90.00  204
 31  ω   -167.00 -78.00   0.50    0.05    --  -92.45-118.00-165.00  178
 32  ω   -157.00 -49.00   0.50    0.05    --  -92.45-161.00  43.00  216
 33  ω   -115.00 -50.00   0.50    0.05    --  -47.30-161.00  43.00  130
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'XtaLAB Synergy, Single source at home/near, HyPix-Arc 100'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1222814000
_diffrn_orient_matrix_UB_12      -0.1226115000
_diffrn_orient_matrix_UB_13      -0.0792509000
_diffrn_orient_matrix_UB_21      -0.1597709000
_diffrn_orient_matrix_UB_22      0.0026642000
_diffrn_orient_matrix_UB_23      -0.1250996000
_diffrn_orient_matrix_UB_31      0.1802255000
_diffrn_orient_matrix_UB_32      0.1580536000
_diffrn_orient_matrix_UB_33      -0.0212260000
_diffrn_oxdiff_digest_frames     
;
01e65775425804872a1205c2c267543a450544228d3
;
_diffrn_oxdiff_digest_hkl        
;
017fae741d46f35cc5d0235bb69082adb83ca5
;
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1660
_reflns_number_total             1892
_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 1.171.43.126a (Rigaku OD, 2024)'
_computing_data_collection       
'CrysAlisPro system (CCD 43.126a 64-bit (release 11-06-2024))'
_computing_data_reduction        'CrysAlisPro 1.171.43.126a (Rigaku OD, 2024)'
_computing_molecular_graphics    'Olex2 1.5-ac5-023 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-ac5-023 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.244
_refine_diff_density_min         -0.180
_refine_diff_density_rms         0.037
_refine_ls_extinction_coef       0.0059(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2019/1 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     129
_refine_ls_number_reflns         1892
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0404
_refine_ls_R_factor_gt           0.0362
_refine_ls_restrained_S_all      1.058
_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)+(0.0552P)²+0.0945P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1011
_refine_ls_wR_factor_ref         0.1057
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C7(H7), C8(H8)
2.c Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C)
;
_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 0.33317(14) 0.63418(11) 0.04047(8) 0.0333(3) Uani 1 1 d . . . . .
O2 O 0.65868(14) 0.72461(10) 0.19014(7) 0.0283(2) Uani 1 1 d . . . . .
N1 N -0.39647(16) 0.03941(12) 0.52445(9) 0.0269(3) Uani 1 1 d . . . . .
C1 C -0.27924(19) 0.14641(14) 0.44574(11) 0.0237(3) Uani 1 1 d . . . . .
C2 C -0.38709(19) 0.17492(15) 0.32951(11) 0.0278(3) Uani 1 1 d . . . . .
H2 H -0.548850 0.123592 0.298964 0.033 Uiso 1 1 calc R U . . .
C3 C -0.25653(19) 0.27852(15) 0.25915(11) 0.0261(3) Uani 1 1 d . . . . .
H3 H -0.330062 0.297513 0.179963 0.031 Uiso 1 1 calc R U . . .
C4 C -0.01833(19) 0.35581(14) 0.30243(11) 0.0223(3) Uani 1 1 d . . . . .
C5 C 0.08621(19) 0.32863(14) 0.42020(11) 0.0243(3) Uani 1 1 d . . . . .
H5 H 0.247195 0.381666 0.451799 0.029 Uiso 1 1 calc R U . . .
C6 C -0.04349(19) 0.22478(14) 0.49121(11) 0.0251(3) Uani 1 1 d . . . . .
H6 H 0.028949 0.207139 0.571156 0.030 Uiso 1 1 calc R U . . .
C7 C 0.11045(19) 0.45851(14) 0.22008(11) 0.0232(3) Uani 1 1 d . . . . .
H7 H 0.023378 0.463913 0.140208 0.028 Uiso 1 1 calc R U . . .
C8 C 0.3341(2) 0.54476(14) 0.24385(11) 0.0247(3) Uani 1 1 d . . . . .
H8 H 0.428731 0.547468 0.323470 0.030 Uiso 1 1 calc R U . . .
C9 C 0.4358(2) 0.63655(14) 0.14648(11) 0.0244(3) Uani 1 1 d . . . . .
C10 C 0.7729(2) 0.81739(17) 0.09948(12) 0.0337(3) Uani 1 1 d . . . . .
H10A H 0.682553 0.899182 0.072735 0.040 Uiso 1 1 calc R U . . .
H10B H 0.783216 0.734643 0.020968 0.040 Uiso 1 1 calc R U . . .
C11 C 1.0133(2) 0.91446(16) 0.16775(12) 0.0307(3) Uani 1 1 d . . . . .
H11A H 1.096829 0.976811 0.108611 0.046 Uiso 1 1 calc R U . . .
H11B H 1.099706 0.832370 0.195208 0.046 Uiso 1 1 calc R U . . .
H11C H 1.000575 0.997725 0.244094 0.046 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 C9 1.2070(14) . ?
O2 C9 1.3403(13) . ?
O2 C10 1.4536(12) . ?
N1 N1 1.2551(19) 2_456 ?
N1 C1 1.4278(14) . ?
C1 C2 1.3963(16) . ?
C1 C6 1.3909(16) . ?
C2 C3 1.3837(14) . ?
C3 C4 1.3987(15) . ?
C4 C5 1.3984(15) . ?
C4 C7 1.4671(14) . ?
C5 C6 1.3873(14) . ?
C7 C8 1.3273(16) . ?
C8 C9 1.4775(14) . ?
C10 C11 1.4976(16) . ?

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
C9 O2 C10 115.18(9) . . ?
N1 N1 C1 114.16(12) 2_456 . ?
C2 C1 N1 124.02(10) . . ?
C6 C1 N1 116.03(10) . . ?
C6 C1 C2 119.95(10) . . ?
C3 C2 C1 119.48(10) . . ?
C2 C3 C4 121.24(10) . . ?
C3 C4 C7 118.06(10) . . ?
C5 C4 C3 118.61(9) . . ?
C5 C4 C7 123.31(10) . . ?
C6 C5 C4 120.47(10) . . ?
C5 C6 C1 120.22(10) . . ?
C8 C7 C4 127.75(10) . . ?
C7 C8 C9 120.01(10) . . ?
O1 C9 O2 123.45(10) . . ?
O1 C9 C8 124.88(10) . . ?
O2 C9 C8 111.67(9) . . ?
O2 C10 C11 107.25(9) . . ?

_shelx_SHELXL_version_number     2019/1
_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 1.176
_oxdiff_exptl_absorpt_empirical_full_min 0.865
####################################################################### 
# 
# 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_jds240052_fa_III
_database_code_depnum_ccdc_archive 'CCDC 2514197'
loop_
_audit_author_name
_audit_author_address
'Paul Waddell'
;Newcastle University
United Kingdom
;
_audit_update_record             
;
2025-12-08 deposited with the CCDC.	2026-02-09 downloaded from the CCDC.
;
_audit_creation_date             2024-08-19
_audit_creation_method           
;
Olex2 1.5-ac5-023
(compiled 2022.04.12 svn.rca3783a0 for Rigaku Oxford Diffraction, GUI svn.r6498)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H22 N2 O4'
_chemical_formula_sum            'C22 H22 N2 O4'
_chemical_formula_weight         378.41
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C22 H24 N2 O4'
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           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   13.4185(5)
_cell_length_b                   9.8231(4)
_cell_length_c                   7.2136(3)
_cell_angle_alpha                90
_cell_angle_beta                 90.961(4)
_cell_angle_gamma                90
_cell_volume                     950.70(7)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4045
_cell_measurement_temperature    150.0(2)
_cell_measurement_theta_max      72.6470
_cell_measurement_theta_min      3.2970
_shelx_estimated_absorpt_T_max   0.993
_shelx_estimated_absorpt_T_min   0.903
_exptl_absorpt_coefficient_mu    0.748
_exptl_absorpt_correction_T_max  0.989
_exptl_absorpt_correction_T_min  0.932
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.126a (Rigaku Oxford Diffraction, 2024)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.322
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             400
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 0 0 0.0104
-1 0 0 0.0044
0 1 -1 0.0538
0 -1 1 0.0538
0 -1 0 0.0345
0 1 0 0.0345
0 -1 -1 0.0608
0 1 1 0.0488

_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.01
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
1.0009 0.0023 0.0001 -0.0727 0.0890 -0.0052
-1.0009 -0.0023 -0.0001 0.0727 -0.0890 0.0052
-0.0012 1.0003 -0.9996 0.2072 0.1649 -0.0072
0.0012 -1.0003 0.9996 -0.2072 -0.1649 0.0072
0.0007 -0.9996 0.0002 -0.0725 -0.0525 0.1287
-0.0007 0.9996 -0.0002 0.0725 0.0525 -0.1287
0.0003 -0.9989 -0.9991 0.0623 0.0599 0.2502
-0.0003 0.9989 0.9991 -0.0623 -0.0599 -0.2502

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0295
_diffrn_reflns_av_unetI/netI     0.0269
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.937
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            8654
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.937
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.437
_diffrn_reflns_theta_min         3.294
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.0(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            'HyPix-Arc 100'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.937
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     26.00 127.00   0.50    1.10    --   46.05  46.00 109.00  202
  2  ω    -35.00  52.00   0.50    1.10    --   46.05 -46.00 -39.00  174
  3  ω   -127.00 -26.00   0.50    1.10    --  -46.92 -46.00 -39.00  202
  4  ω   -173.00 -72.00   0.50    4.40    --  -92.45 -46.00 -39.00  202
  5  ω   -173.00 -72.00   0.50    4.40    --  -92.45 -46.00 -39.00  202
  6  ω    -52.00 -12.00   0.50    4.40    --  -92.45  46.00 109.00   80
  7  ω     77.00 178.00   0.50    4.40    --   97.16  46.00 109.00  202
  8  ω     17.00  52.00   0.50    4.40    --   97.16 -46.00 -39.00   70
  9  ω     74.00 122.00   0.50    1.10    --   46.05 125.00 -30.00   96
 10  ω    -52.00  34.00   0.50    1.10    --  -46.92  46.00 109.00  172
 11  ω   -166.00 -83.00   0.50    4.40    --  -92.45 -95.00-120.00  166
 12  ω    -51.00 -11.00   0.50    4.40    --  -92.45  45.00 -90.00   80
 13  ω   -166.00 -83.00   0.50    4.40    --  -92.45 -95.00-120.00  166
 14  ω    -71.00 -15.00   0.50    4.40    --  -92.45  61.00 -90.00  112
 15  ω    -51.00 -11.00   0.50    4.40    --  -92.45  45.00 -30.00   80
 16  ω    -51.00 -11.00   0.50    4.40    --  -92.45  45.00  60.00   80
 17  ω    -51.00 -11.00   0.50    4.40    --  -92.45  45.00-120.00   80
 18  ω     16.00  51.00   0.50    4.40    --   97.16 -45.00 150.00   70
 19  ω     27.00 105.00   0.50    4.40    --   97.16 -77.00  60.00  156
 20  ω     35.00 105.00   0.50    4.40    --  108.12 -95.00   0.00  140
 21  ω     36.00  71.00   0.50    4.40    --  108.12 -61.00  90.00   70
 22  ω     42.00 102.00   0.50    4.40    --  108.12 -77.00-150.00  120
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'XtaLAB Synergy, Single source at home/near, HyPix-Arc 100'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0727389000
_diffrn_orient_matrix_UB_12      0.0723939000
_diffrn_orient_matrix_UB_13      -0.1347320000
_diffrn_orient_matrix_UB_21      0.0888083000
_diffrn_orient_matrix_UB_22      0.0525494000
_diffrn_orient_matrix_UB_23      -0.1124397000
_diffrn_orient_matrix_UB_31      -0.0048472000
_diffrn_orient_matrix_UB_32      -0.1287628000
_diffrn_orient_matrix_UB_33      -0.1216320000
_diffrn_oxdiff_digest_frames     
;
01828faa26fb282caa983d35c4363654d902922d712
;
_diffrn_oxdiff_digest_hkl        
;
019f813f56b11bb2bc668792eacae6f82c43dc
;
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1601
_reflns_number_total             1866
_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 1.171.43.126a (Rigaku OD, 2024)'
_computing_data_collection       'CrysAlisPro 1.171.43.126a (Rigaku OD, 2024)'
_computing_data_reduction        'CrysAlisPro 1.171.43.126a (Rigaku OD, 2024)'
_computing_molecular_graphics    'Olex2 1.5-ac5-023 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-ac5-023 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.221
_refine_diff_density_min         -0.172
_refine_diff_density_rms         0.039
_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     128
_refine_ls_number_reflns         1866
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0455
_refine_ls_R_factor_gt           0.0386
_refine_ls_restrained_S_all      1.067
_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)+(0.0474P)²+0.2826P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0977
_refine_ls_wR_factor_ref         0.1032
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C7(H7), C8(H8)
2.c Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C)
;
_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 0.13625(7) 0.35688(10) 0.98195(13) 0.0350(3) Uani 1 1 d . . . . .
O2 O 0.15302(7) 0.56693(9) 1.10176(12) 0.0334(3) Uani 1 1 d . . . . .
N1 N 0.49408(8) 0.54924(11) 0.05499(14) 0.0289(3) Uani 1 1 d . . . . .
C1 C 0.43161(10) 0.51861(13) 0.20755(17) 0.0265(3) Uani 1 1 d . . . . .
C2 C 0.37555(10) 0.39981(13) 0.22183(17) 0.0274(3) Uani 1 1 d . . . . .
H2 H 0.377800 0.332652 0.127225 0.033 Uiso 1 1 calc R U . . .
C3 C 0.31666(10) 0.38060(13) 0.37492(17) 0.0277(3) Uani 1 1 d . . . . .
H3 H 0.278246 0.299716 0.384168 0.033 Uiso 1 1 calc R U . . .
C4 C 0.31230(10) 0.47772(13) 0.51689(17) 0.0269(3) Uani 1 1 d . . . . .
C5 C 0.36812(10) 0.59724(13) 0.49971(17) 0.0298(3) Uani 1 1 d . . . . .
H5 H 0.365461 0.664937 0.593551 0.036 Uiso 1 1 calc R U . . .
C6 C 0.42731(10) 0.61733(13) 0.34630(17) 0.0295(3) Uani 1 1 d . . . . .
H6 H 0.465087 0.698665 0.335641 0.035 Uiso 1 1 calc R U . . .
C7 C 0.24876(10) 0.44772(13) 0.67544(17) 0.0283(3) Uani 1 1 d . . . . .
H7 H 0.210851 0.366204 0.667095 0.034 Uiso 1 1 calc R U . . .
C8 C 0.23760(10) 0.52042(14) 0.82951(18) 0.0308(3) Uani 1 1 d . . . . .
H8 H 0.272261 0.604047 0.845374 0.037 Uiso 1 1 calc R U . . .
C9 C 0.17100(10) 0.47035(13) 0.97571(17) 0.0287(3) Uani 1 1 d . . . . .
C10 C 0.08368(11) 0.52982(15) 1.24646(18) 0.0332(3) Uani 1 1 d . . . . .
H10A H 0.111308 0.454404 1.322470 0.040 Uiso 1 1 calc R U . . .
H10B H 0.019406 0.499853 1.190781 0.040 Uiso 1 1 calc R U . . .
C11 C 0.06868(14) 0.65330(17) 1.3638(2) 0.0493(4) Uani 1 1 d . . . . .
H11A H 0.040853 0.726910 1.287230 0.074 Uiso 1 1 calc R U . . .
H11B H 0.132811 0.682164 1.417581 0.074 Uiso 1 1 calc R U . . .
H11C H 0.022528 0.631776 1.463499 0.074 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 C9 1.2093(16) . ?
O2 C9 1.3388(16) . ?
O2 C10 1.4563(16) . ?
N1 N1 1.263(2) 3_665 ?
N1 C1 1.4266(17) . ?
C1 C2 1.3932(19) . ?
C1 C6 1.3956(18) . ?
C2 C3 1.3816(18) . ?
C3 C4 1.4016(18) . ?
C4 C5 1.3993(19) . ?
C4 C7 1.4678(18) . ?
C5 C6 1.3870(18) . ?
C7 C8 1.3317(19) . ?
C8 C9 1.4779(19) . ?
C10 C11 1.495(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
C9 O2 C10 115.72(10) . . ?
N1 N1 C1 113.88(13) 3_665 . ?
C2 C1 N1 123.97(12) . . ?
C2 C1 C6 120.01(12) . . ?
C6 C1 N1 116.02(11) . . ?
C3 C2 C1 119.36(12) . . ?
C2 C3 C4 121.50(12) . . ?
C3 C4 C7 117.68(12) . . ?
C5 C4 C3 118.52(12) . . ?
C5 C4 C7 123.80(12) . . ?
C6 C5 C4 120.30(12) . . ?
C5 C6 C1 120.30(12) . . ?
C8 C7 C4 128.14(13) . . ?
C7 C8 C9 119.66(13) . . ?
O1 C9 O2 123.63(12) . . ?
O1 C9 C8 124.85(12) . . ?
O2 C9 C8 111.52(11) . . ?
O2 C10 C11 107.25(12) . . ?

_shelx_SHELXL_version_number     2019/1
_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 1.389
_oxdiff_exptl_absorpt_empirical_full_min 0.712
####################################################################### 
# 
# 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_jds240049_fa_II
_database_code_depnum_ccdc_archive 'CCDC 2514196'
loop_
_audit_author_name
_audit_author_address
'Paul Waddell'
;Newcastle University
United Kingdom
;
_audit_update_record             
;
2025-12-08 deposited with the CCDC.	2026-02-09 downloaded from the CCDC.
;
_audit_creation_date             2024-08-12
_audit_creation_method           
;
Olex2 1.5-ac5-023
(compiled 2022.04.12 svn.rca3783a0 for Rigaku Oxford Diffraction, GUI svn.r6498)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H22 N2 O4'
_chemical_formula_sum            'C22 H22 N2 O4'
_chemical_formula_weight         378.41
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C19 H21 N1 O6 S1'
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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   3.91720(10)
_cell_length_b                   9.6395(2)
_cell_length_c                   50.1648(11)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1894.22(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5273
_cell_measurement_temperature    150.0(2)
_cell_measurement_theta_max      73.2820
_cell_measurement_theta_min      3.5200
_shelx_estimated_absorpt_T_max   0.985
_shelx_estimated_absorpt_T_min   0.795
_exptl_absorpt_coefficient_mu    0.751
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.698
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.126a (Rigaku Oxford Diffraction, 2024)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.327
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plank
_exptl_crystal_F_000             800
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 0 -1 0.0179
0 0 1 0.0059
0 -1 0 0.0209
0 1 0 0.0259
1 0 -1 0.1575
-1 0 1 0.1575

_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.02
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
0.0000 0.0000 -1.0001 -0.0177 0.0251 0.0014
-0.0000 -0.0000 1.0001 0.0177 -0.0251 -0.0014
-0.0002 -1.0005 0.0010 0.1280 0.0919 -0.0269
0.0002 1.0005 -0.0010 -0.1280 -0.0919 0.0269
0.9994 -0.0008 -0.9901 0.0465 0.0485 0.3885
-0.9994 0.0008 0.9901 -0.0465 -0.0485 -0.3885

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0250
_diffrn_reflns_av_unetI/netI     0.0338
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -1
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       60
_diffrn_reflns_limit_l_min       -62
_diffrn_reflns_number            8816
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.965
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.640
_diffrn_reflns_theta_min         3.524
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.0(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            'HyPix-Arc 100'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -137.00-111.00   0.25    1.57    --  -96.07 -95.00   0.00  104
  2  ω    -51.00 -17.00   0.25    1.57    --  -96.07  45.00  30.00  136
  3  ω     14.00  48.00   0.25    0.39    --  -38.83  38.00 -30.00  136
  4  ω    -33.00   8.00   0.25    0.39    --  -38.83  38.00 -30.00  164
  5  ω    -24.00   8.00   0.25    0.39    --  -38.83  13.00 -73.00  128
  6  ω     40.00  66.00   0.25    0.39    --   35.33-178.00   0.00  104
  7  ω     80.00 118.00   0.25    0.39    --   35.33-178.00   0.00  152
  8  ω     28.00  77.00   0.25    1.57    --  104.27-129.00 -91.00  196
  9  ω     43.00 106.00   0.25    1.57    --  111.20-111.00 -90.00  252
 10  ω     34.00 104.00   0.25    1.57    --  104.27-115.00  -8.00  280
 11  ω     -9.00  23.00   0.25    0.39    --   35.33 -13.00 114.00  128
 12  ω     14.00  48.00   0.25    1.57    --  104.27 -45.00 150.00  136
 13  ω     18.00  43.00   0.25    1.57    --  104.27 -45.00 120.00  100
 14  ω    -51.00 -20.00   0.25    0.39    --   35.33 -13.00 114.00  124
 15  ω     45.00  70.00   0.25    1.57    --  111.20 -61.00  60.00  100
 16  ω     49.00 171.00   0.25    1.57    --  111.20  13.00 -73.00  488
 17  ω     71.00  97.00   0.25    0.39    --   35.33 171.00-137.00  104
 18  ω   -100.00 -70.00   0.25    0.39    --  -38.83-142.00  97.00  120
 19  ω     50.00  93.00   0.25    0.39    --   35.58 178.00  90.00  172
 20  ω    -59.00 -13.00   0.25    1.57    --  -96.07  61.00  90.00  184
 21  ω     17.00  43.00   0.25    1.57    --  104.27 -45.00-150.00  104
 22  ω     14.00  45.00   0.25    1.57    --  104.27 -45.00-120.00  124
 23  ω     14.00  39.00   0.25    1.57    --  104.27 -45.00 -90.00  100
 24  ω     21.00  46.00   0.25    1.57    --  111.20 -45.00-180.00  100
 25  ω     27.00  52.00   0.25    1.57    --  111.20 -61.00   0.00  100
 26  ω     21.00  48.00   0.25    1.57    --  111.20 -45.00 -60.00  108
 27  ω     37.00  63.00   0.25    1.57    --  111.20 -77.00 -60.00  104
 28  ω     77.00 103.00   0.25    1.57    --  111.20 -77.00 -60.00  104
 29  ω     27.00  52.00   0.25    1.57    --  111.20 -61.00 -30.00  100
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'XtaLAB Synergy, Single source at home/near, HyPix-Arc 100'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0639827000
_diffrn_orient_matrix_UB_12      -0.1279370000
_diffrn_orient_matrix_UB_13      0.0177047000
_diffrn_orient_matrix_UB_21      0.0236173000
_diffrn_orient_matrix_UB_22      -0.0918816000
_diffrn_orient_matrix_UB_23      -0.0250567000
_diffrn_orient_matrix_UB_31      0.3873948000
_diffrn_orient_matrix_UB_32      0.0267913000
_diffrn_orient_matrix_UB_33      -0.0014088000
_diffrn_oxdiff_digest_frames     
;
01b47cd8c44bbeecc96111008d78cd7a2a04252f643
;
_diffrn_oxdiff_digest_hkl        
;
015fbbdc20dc2dd5016bc9e4f8d6679713b33f
;
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.614
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.937
_reflns_number_gt                3336
_reflns_number_total             3665
_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 1.171.43.126a (Rigaku OD, 2024)'
_computing_data_collection       
'CrysAlisPro system (CCD 43.126a 64-bit (release 11-06-2024))'
_computing_data_reduction        'CrysAlisPro 1.171.43.126a (Rigaku OD, 2024)'
_computing_molecular_graphics    'Olex2 1.5-ac5-023 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-ac5-023 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.287
_refine_diff_density_min         -0.137
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details 
;
 Flack x determined using 1225 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.04(13)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     255
_refine_ls_number_reflns         3665
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0398
_refine_ls_R_factor_gt           0.0356
_refine_ls_restrained_S_all      1.044
_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)+(0.0582P)²+0.0877P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0915
_refine_ls_wR_factor_ref         0.0942
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C21(H21A,H21B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C7(H7), C8(H8), C13(H13), C14(H14), C16(H16),
 C17(H17), C18(H18), C19(H19)
2.c Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C22(H22A,H22B,H22C)
;
_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 1.2133(5) 0.93657(16) 0.11605(3) 0.0382(4) Uani 1 1 d . . . . .
O2 O 0.9874(4) 0.73376(15) 0.10271(3) 0.0308(3) Uani 1 1 d . . . . .
O3 O 0.2742(6) 0.80677(17) 0.45871(3) 0.0450(4) Uani 1 1 d . . . . .
O4 O 0.0882(5) 0.58703(16) 0.45483(3) 0.0368(4) Uani 1 1 d . . . . .
N1 N 0.6320(4) 0.77291(17) 0.27685(3) 0.0250(4) Uani 1 1 d . . . . .
N2 N 0.6926(4) 0.87065(17) 0.29273(3) 0.0253(4) Uani 1 1 d . . . . .
C1 C 0.7292(5) 0.80313(19) 0.24996(4) 0.0226(4) Uani 1 1 d . . . . .
C2 C 0.9149(5) 0.9202(2) 0.24245(4) 0.0234(4) Uani 1 1 d . . . . .
H2 H 0.984110 0.985981 0.255472 0.028 Uiso 1 1 calc R U . . .
C3 C 0.9976(5) 0.93990(19) 0.21598(4) 0.0242(4) Uani 1 1 d . . . . .
H3 H 1.123348 1.019950 0.210909 0.029 Uiso 1 1 calc R U . . .
C4 C 0.8996(5) 0.8440(2) 0.19645(4) 0.0230(4) Uani 1 1 d . . . . .
C5 C 0.7146(5) 0.72649(19) 0.20443(4) 0.0241(4) Uani 1 1 d . . . . .
H5 H 0.646705 0.660093 0.191480 0.029 Uiso 1 1 calc R U . . .
C6 C 0.6301(5) 0.70612(19) 0.23078(4) 0.0244(4) Uani 1 1 d . . . . .
H6 H 0.504557 0.626152 0.235911 0.029 Uiso 1 1 calc R U . . .
C7 C 1.0011(5) 0.8690(2) 0.16880(4) 0.0258(4) Uani 1 1 d . . . . .
H7 H 1.138241 0.948710 0.165709 0.031 Uiso 1 1 calc R U . . .
C8 C 0.9239(5) 0.7932(2) 0.14750(4) 0.0265(4) Uani 1 1 d . . . . .
H8 H 0.782106 0.713837 0.149354 0.032 Uiso 1 1 calc R U . . .
C9 C 1.0567(5) 0.8316(2) 0.12106(4) 0.0273(4) Uani 1 1 d . . . . .
C10 C 1.1182(6) 0.7616(2) 0.07621(4) 0.0333(5) Uani 1 1 d . . . . .
H10A H 1.366303 0.780758 0.076985 0.040 Uiso 1 1 calc R U . . .
H10B H 1.002294 0.843524 0.068470 0.040 Uiso 1 1 calc R U . . .
C11 C 1.0509(7) 0.6356(3) 0.05943(5) 0.0397(5) Uani 1 1 d . . . . .
H11A H 1.145105 0.649903 0.041545 0.060 Uiso 1 1 calc R U . . .
H11B H 0.804253 0.620021 0.058168 0.060 Uiso 1 1 calc R U . . .
H11C H 1.159581 0.554574 0.067639 0.060 Uiso 1 1 calc R U . . .
C12 C 0.6075(5) 0.8437(2) 0.31975(4) 0.0233(4) Uani 1 1 d . . . . .
C13 C 0.4430(5) 0.7240(2) 0.32920(4) 0.0250(4) Uani 1 1 d . . . . .
H13 H 0.377340 0.653030 0.317100 0.030 Uiso 1 1 calc R U . . .
C14 C 0.3769(5) 0.7094(2) 0.35603(4) 0.0259(4) Uani 1 1 d . . . . .
H14 H 0.265113 0.628178 0.362280 0.031 Uiso 1 1 calc R U . . .
C15 C 0.4728(5) 0.8133(2) 0.37431(4) 0.0248(4) Uani 1 1 d . . . . .
C16 C 0.6356(5) 0.9317(2) 0.36459(4) 0.0273(4) Uani 1 1 d . . . . .
H16 H 0.701345 1.002947 0.376634 0.033 Uiso 1 1 calc R U . . .
C17 C 0.7026(5) 0.9469(2) 0.33764(4) 0.0266(4) Uani 1 1 d . . . . .
H17 H 0.814004 1.028127 0.331356 0.032 Uiso 1 1 calc R U . . .
C18 C 0.4044(6) 0.8029(2) 0.40285(4) 0.0283(4) Uani 1 1 d . . . . .
H18 H 0.462954 0.881739 0.413241 0.034 Uiso 1 1 calc R U . . .
C19 C 0.2713(6) 0.6973(2) 0.41598(4) 0.0322(5) Uani 1 1 d . . . . .
H19 H 0.210896 0.614990 0.406686 0.039 Uiso 1 1 calc R U . . .
C20 C 0.2157(6) 0.7064(2) 0.44511(4) 0.0312(5) Uani 1 1 d . . . . .
C21 C 0.0031(7) 0.5887(2) 0.48297(4) 0.0362(5) Uani 1 1 d . . . . .
H21A H -0.172728 0.659964 0.486618 0.043 Uiso 1 1 calc R U . . .
H21B H 0.208113 0.610154 0.493747 0.043 Uiso 1 1 calc R U . . .
C22 C -0.1304(7) 0.4468(3) 0.48985(5) 0.0429(6) Uani 1 1 d . . . . .
H22A H -0.333103 0.426800 0.479059 0.064 Uiso 1 1 calc R U . . .
H22B H -0.191151 0.443776 0.508794 0.064 Uiso 1 1 calc R U . . .
H22C H 0.045999 0.377250 0.486181 0.064 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 C9 1.209(3) . ?
O2 C9 1.346(3) . ?
O2 C10 1.450(2) . ?
O3 C20 1.206(3) . ?
O4 C20 1.346(3) . ?
O4 C21 1.451(2) . ?
N1 N2 1.256(2) . ?
N1 C1 1.432(2) . ?
N2 C12 1.420(2) . ?
C1 C2 1.395(3) . ?
C1 C6 1.397(3) . ?
C2 C3 1.380(3) . ?
C3 C4 1.401(3) . ?
C4 C5 1.403(3) . ?
C4 C7 1.463(3) . ?
C5 C6 1.377(3) . ?
C7 C8 1.329(3) . ?
C8 C9 1.472(3) . ?
C10 C11 1.501(3) . ?
C12 C13 1.404(3) . ?
C12 C17 1.391(3) . ?
C13 C14 1.377(3) . ?
C14 C15 1.409(3) . ?
C15 C16 1.396(3) . ?
C15 C18 1.460(3) . ?
C16 C17 1.385(3) . ?
C18 C19 1.320(3) . ?
C19 C20 1.480(3) . ?
C21 C22 1.505(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
C9 O2 C10 115.22(16) . . ?
C20 O4 C21 115.39(17) . . ?
N2 N1 C1 113.24(16) . . ?
N1 N2 C12 115.05(16) . . ?
C2 C1 N1 123.91(17) . . ?
C2 C1 C6 120.04(18) . . ?
C6 C1 N1 116.05(17) . . ?
C3 C2 C1 119.60(18) . . ?
C2 C3 C4 121.17(18) . . ?
C3 C4 C5 118.36(18) . . ?
C3 C4 C7 118.64(18) . . ?
C5 C4 C7 122.98(18) . . ?
C6 C5 C4 120.89(18) . . ?
C5 C6 C1 119.94(18) . . ?
C8 C7 C4 127.54(19) . . ?
C7 C8 C9 120.36(19) . . ?
O1 C9 O2 123.14(19) . . ?
O1 C9 C8 125.22(19) . . ?
O2 C9 C8 111.63(18) . . ?
O2 C10 C11 107.59(19) . . ?
C13 C12 N2 125.50(18) . . ?
C17 C12 N2 114.96(17) . . ?
C17 C12 C13 119.54(18) . . ?
C14 C13 C12 120.02(18) . . ?
C13 C14 C15 120.86(19) . . ?
C14 C15 C18 122.72(18) . . ?
C16 C15 C14 118.43(18) . . ?
C16 C15 C18 118.85(18) . . ?
C17 C16 C15 120.93(18) . . ?
C16 C17 C12 120.22(18) . . ?
C19 C18 C15 127.95(19) . . ?
C18 C19 C20 120.34(19) . . ?
O3 C20 O4 123.45(19) . . ?
O3 C20 C19 125.3(2) . . ?
O4 C20 C19 111.21(17) . . ?
O4 C21 C22 107.05(18) . . ?

_shelx_SHELXL_version_number     2019/1
_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 1.524
_oxdiff_exptl_absorpt_empirical_full_min 0.684
####################################################################### 
# 
# 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_jds240050_fa_SM1
_database_code_depnum_ccdc_archive 'CCDC 2514199'
loop_
_audit_author_name
_audit_author_address
'Paul Waddell'
;Newcastle University
United Kingdom
;
_audit_update_record             
;
2025-12-08 deposited with the CCDC.	2026-02-09 downloaded from the CCDC.
;
_audit_creation_date             2024-08-16
_audit_creation_method           
;
Olex2 1.5-ac5-023
(compiled 2022.04.12 svn.rca3783a0 for Rigaku Oxford Diffraction, GUI svn.r6498)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C11 H13 N O2'
_chemical_formula_sum            'C11 H13 N O2'
_chemical_formula_weight         191.22
_chemical_absolute_configuration unk
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C11 H12 N1 O2'
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      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'
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'

_cell_length_a                   22.6748(7)
_cell_length_b                   8.4634(3)
_cell_length_c                   5.3937(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1035.08(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2135
_cell_measurement_temperature    150.0(2)
_cell_measurement_theta_max      74.3630
_cell_measurement_theta_min      3.8930
_shelx_estimated_absorpt_T_max   0.986
_shelx_estimated_absorpt_T_min   0.836
_exptl_absorpt_coefficient_mu    0.687
_exptl_absorpt_correction_T_max  0.988
_exptl_absorpt_correction_T_min  0.921
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.126a (Rigaku Oxford Diffraction, 2024)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.227
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             408
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 0 0 0.0079
-1 0 0 0.0099
0 0 -1 0.0122
0 0 1 0.0182
0 1 2 0.0610
0 -1 -2 0.0787

_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
1.0000 0.0000 -0.0000 0.0411 -0.0484 -0.0242
-1.0000 -0.0000 0.0000 -0.0411 0.0484 0.0242
-0.0000 0.0000 -1.0000 0.1441 0.1074 0.0296
0.0000 -0.0000 1.0000 -0.1441 -0.1074 -0.0296
0.0001 1.0000 2.0000 -0.2611 -0.3231 0.2036
-0.0001 -1.0000 -2.0000 0.2611 0.3231 -0.2036

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0305
_diffrn_reflns_av_unetI/netI     0.0332
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.935
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -2
_diffrn_reflns_number            3449
_diffrn_reflns_point_group_measured_fraction_full 0.717
_diffrn_reflns_point_group_measured_fraction_max 0.656
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.664
_diffrn_reflns_theta_min         3.899
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.0(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            'HyPix-Arc 100'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.935
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     -6.00  34.00   0.50    1.21    --   46.55 -30.00  23.00   80
  2  ω     16.00  51.00   0.50    1.21    --   97.16 -45.00   0.00   70
  3  ω     32.00  57.00   0.50    1.21    --  108.12 -61.00  60.00   50
  4  ω     21.00  47.00   0.50    1.21    --   97.16 -45.00  90.00   52
  5  ω     41.00 100.00   0.50    1.21    --   97.16-115.00 172.00  118
  6  ω     37.00 103.00   0.50    1.21    --  108.12 -95.00-150.00  132
  7  ω    -53.00  -5.00   0.50    1.21    --  -47.30  57.00-150.00   96
  8  ω    -43.00 -13.00   0.50    1.21    --  -92.45  45.00-180.00   60
  9  ω    -19.00  32.00   0.50    1.21    --  -47.30  19.00 -90.00  102
 10  ω    -76.00 -51.00   0.50    1.21    --  -92.45  96.00   4.00   50
 11  ω    -51.00 -12.00   0.50    1.21    --  -92.45  45.00   0.00   78
 12  ω   -166.00-102.00   0.50    1.21    --  -92.45 -30.00  23.00  128
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'XtaLAB Synergy, Single source at home/near, HyPix-Arc 100'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0411100000
_diffrn_orient_matrix_UB_12      0.0270049000
_diffrn_orient_matrix_UB_13      -0.1440593000
_diffrn_orient_matrix_UB_21      -0.0483741000
_diffrn_orient_matrix_UB_22      -0.1082782000
_diffrn_orient_matrix_UB_23      -0.1074256000
_diffrn_orient_matrix_UB_31      -0.0242317000
_diffrn_orient_matrix_UB_32      0.2627187000
_diffrn_orient_matrix_UB_33      -0.0295622000
_diffrn_oxdiff_digest_frames     
;
0194f107880116dfe77c927c53c1b9d28b010169d63
;
_diffrn_oxdiff_digest_hkl        
;
010c24001fef82565358ecc3a4b333aa3e22c9
;
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.265
_reflns_Friedel_fraction_full    0.360
_reflns_Friedel_fraction_max     0.309
_reflns_number_gt                1289
_reflns_number_total             1435
_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 1.171.43.126a (Rigaku OD, 2024)'
_computing_data_collection       
'CrysAlisPro system (CCD 43.126a 64-bit (release 11-06-2024))'
_computing_data_reduction        'CrysAlisPro 1.171.43.126a (Rigaku OD, 2024)'
_computing_molecular_graphics    'Olex2 1.5-ac5-023 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-ac5-023 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.216
_refine_diff_density_min         -0.154
_refine_diff_density_rms         0.036
_refine_ls_abs_structure_details 
;
 Flack x determined using 252 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.2(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     134
_refine_ls_number_reflns         1435
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0431
_refine_ls_R_factor_gt           0.0381
_refine_ls_restrained_S_all      1.050
_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)+(0.0531P)²+0.1849P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0972
_refine_ls_wR_factor_ref         0.1009
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C7(H7), C8(H8)
2.c Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C)
;
_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 0.62433(8) 0.0125(2) 0.8175(5) 0.0401(5) Uani 1 1 d . . . . .
O2 O 0.68635(8) -0.0340(2) 0.5036(4) 0.0379(5) Uani 1 1 d . . . . .
N1 N 0.54080(11) 0.9227(3) 0.2352(5) 0.0353(5) Uani 1 1 d . . . . .
H1A H 0.5248(13) 0.981(4) 0.348(7) 0.042 Uiso 1 1 d . U . . .
H1B H 0.5658(14) 0.960(4) 0.139(7) 0.042 Uiso 1 1 d . U . . .
C1 C 0.58634(10) 0.4669(3) 0.4863(5) 0.0286(6) Uani 1 1 d . . . . .
C2 C 0.60969(11) 0.5287(3) 0.2657(5) 0.0314(6) Uani 1 1 d . . . . .
H2 H 0.635814 0.465760 0.169723 0.038 Uiso 1 1 calc R U . . .
C3 C 0.59553(11) 0.6790(3) 0.1849(5) 0.0305(6) Uani 1 1 d . . . . .
H3 H 0.612529 0.718171 0.036140 0.037 Uiso 1 1 calc R U . . .
C4 C 0.55652(10) 0.7741(3) 0.3192(5) 0.0270(5) Uani 1 1 d . . . . .
C5 C 0.53275(11) 0.7130(3) 0.5393(5) 0.0306(6) Uani 1 1 d . . . . .
H5 H 0.506278 0.775388 0.634348 0.037 Uiso 1 1 calc R U . . .
C6 C 0.54741(10) 0.5630(3) 0.6191(5) 0.0295(5) Uani 1 1 d . . . . .
H6 H 0.530592 0.524148 0.768474 0.035 Uiso 1 1 calc R U . . .
C7 C 0.60024(10) 0.3111(3) 0.5867(5) 0.0317(6) Uani 1 1 d . . . . .
H7 H 0.582071 0.284989 0.739995 0.038 Uiso 1 1 calc R U . . .
C8 C 0.63520(11) 0.2016(3) 0.4896(5) 0.0347(6) Uani 1 1 d . . . . .
H8 H 0.653084 0.219148 0.332741 0.042 Uiso 1 1 calc R U . . .
C9 C 0.64640(11) 0.0535(3) 0.6230(6) 0.0336(6) Uani 1 1 d . . . . .
C10 C 0.70222(11) -0.1820(3) 0.6174(6) 0.0360(6) Uani 1 1 d . . . . .
H10A H 0.666799 -0.249263 0.637189 0.043 Uiso 1 1 calc R U . . .
H10B H 0.719474 -0.163140 0.783336 0.043 Uiso 1 1 calc R U . . .
C11 C 0.74658(12) -0.2632(4) 0.4525(7) 0.0475(8) Uani 1 1 d . . . . .
H11A H 0.728534 -0.285652 0.291242 0.071 Uiso 1 1 calc R U . . .
H11B H 0.759161 -0.362379 0.529906 0.071 Uiso 1 1 calc R U . . .
H11C H 0.780862 -0.194252 0.429342 0.071 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 C9 1.213(4) . ?
O2 C9 1.335(3) . ?
O2 C10 1.441(3) . ?
N1 H1A 0.86(4) . ?
N1 H1B 0.83(4) . ?
N1 C4 1.383(3) . ?
C1 C2 1.403(4) . ?
C1 C6 1.398(4) . ?
C1 C7 1.460(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.382(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.398(3) . ?
C4 C5 1.402(4) . ?
C5 H5 0.9500 . ?
C5 C6 1.381(4) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C7 C8 1.328(3) . ?
C8 H8 0.9500 . ?
C8 C9 1.467(4) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C11 1.508(4) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 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
C9 O2 C10 116.5(2) . . ?
H1A N1 H1B 121(3) . . ?
C4 N1 H1A 113(2) . . ?
C4 N1 H1B 112(2) . . ?
C2 C1 C7 124.7(2) . . ?
C6 C1 C2 117.1(2) . . ?
C6 C1 C7 118.1(2) . . ?
C1 C2 H2 119.3 . . ?
C3 C2 C1 121.5(2) . . ?
C3 C2 H2 119.3 . . ?
C2 C3 H3 119.6 . . ?
C2 C3 C4 120.9(2) . . ?
C4 C3 H3 119.6 . . ?
N1 C4 C3 121.1(2) . . ?
N1 C4 C5 120.9(2) . . ?
C3 C4 C5 118.0(2) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 C4 120.7(2) . . ?
C6 C5 H5 119.7 . . ?
C1 C6 H6 119.1 . . ?
C5 C6 C1 121.8(2) . . ?
C5 C6 H6 119.1 . . ?
C1 C7 H7 116.1 . . ?
C8 C7 C1 127.8(3) . . ?
C8 C7 H7 116.1 . . ?
C7 C8 H8 119.8 . . ?
C7 C8 C9 120.4(2) . . ?
C9 C8 H8 119.8 . . ?
O1 C9 O2 122.6(2) . . ?
O1 C9 C8 126.7(2) . . ?
O2 C9 C8 110.8(2) . . ?
O2 C10 H10A 110.1 . . ?
O2 C10 H10B 110.1 . . ?
O2 C10 C11 108.2(2) . . ?
H10A C10 H10B 108.4 . . ?
C11 C10 H10A 110.1 . . ?
C11 C10 H10B 110.1 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N1 H1A N1 0.86(4) 2.69(4) 3.523(3) 162(3) 2_675 yes
N1 H1B O1 0.83(4) 2.23(4) 3.040(4) 165(3) 1_564 yes

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
N1 C4 C5 C6 178.4(2) . . . . ?
C1 C2 C3 C4 -1.0(4) . . . . ?
C1 C7 C8 C9 177.0(2) . . . . ?
C2 C1 C6 C5 -0.6(4) . . . . ?
C2 C1 C7 C8 -1.5(4) . . . . ?
C2 C3 C4 N1 -178.0(2) . . . . ?
C2 C3 C4 C5 0.7(4) . . . . ?
C3 C4 C5 C6 -0.3(3) . . . . ?
C4 C5 C6 C1 0.3(4) . . . . ?
C6 C1 C2 C3 0.9(4) . . . . ?
C6 C1 C7 C8 179.1(3) . . . . ?
C7 C1 C2 C3 -178.5(2) . . . . ?
C7 C1 C6 C5 178.9(2) . . . . ?
C7 C8 C9 O1 3.9(4) . . . . ?
C7 C8 C9 O2 -174.8(2) . . . . ?
C9 O2 C10 C11 179.0(2) . . . . ?
C10 O2 C9 O1 0.2(4) . . . . ?
C10 O2 C9 C8 179.0(2) . . . . ?

_shelx_SHELXL_version_number     2019/1
_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 1.280
_oxdiff_exptl_absorpt_empirical_full_min 0.773
####################################################################### 
# 
# 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_jds250024_fa_SM2
_database_code_depnum_ccdc_archive 'CCDC 2514200'
loop_
_audit_author_name
_audit_author_address
'Paul Waddell'
;Newcastle University
United Kingdom
;
_audit_update_record             
;
2025-12-08 deposited with the CCDC.	2026-02-09 downloaded from the CCDC.
;
_audit_creation_date             2025-05-13
_audit_creation_method           
;
Olex2 1.5-ac5-023
(compiled 2022.04.12 svn.rca3783a0 for Rigaku Oxford Diffraction, GUI svn.r6498)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C11 H11 N O4'
_chemical_formula_sum            'C11 H11 N O4'
_chemical_formula_weight         221.21
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C11 H11 N1 O4'
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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.9802(3)
_cell_length_b                   8.0029(4)
_cell_length_c                   10.9422(7)
_cell_angle_alpha                69.905(5)
_cell_angle_beta                 72.221(5)
_cell_angle_gamma                68.201(5)
_cell_volume                     521.80(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5098
_cell_measurement_temperature    150.0(2)
_cell_measurement_theta_max      75.8160
_cell_measurement_theta_min      4.3910
_shelx_estimated_absorpt_T_max   0.973
_shelx_estimated_absorpt_T_min   0.875
_exptl_absorpt_coefficient_mu    0.914
_exptl_absorpt_correction_T_max  0.976
_exptl_absorpt_correction_T_min  0.907
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.126a (Rigaku Oxford Diffraction, 2024)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.408
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             232
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 0 -1 0.0190
0 0 1 0.0090
0 -1 0 0.0400
0 1 0 0.0620
-1 0 0 0.0559
1 0 0 0.0569
1 2 0 0.0565
1 1 0 0.0594

_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.03
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-0.0000 -0.0000 -1.0000 0.1055 -0.1098 -0.0156
0.0000 0.0000 1.0000 -0.1055 0.1098 0.0156
-0.0000 -1.0000 -0.0000 0.0788 0.1688 -0.1068
0.0000 1.0000 0.0000 -0.0788 -0.1688 0.1068
-1.0000 -0.0000 -0.0000 0.0158 0.0505 0.2370
1.0000 0.0000 0.0000 -0.0158 -0.0505 -0.2370
1.0000 2.0000 0.0000 -0.1734 -0.3881 -0.0234
1.0000 1.0000 0.0000 -0.0946 -0.2193 -0.1302

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0296
_diffrn_reflns_av_unetI/netI     0.0260
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.931
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            9705
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.931
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.104
_diffrn_reflns_theta_min         4.395
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.0(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            'HyPix-Arc 100'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.931
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     35.00 130.00   0.50    0.45    --  107.32-151.00 112.00  190
  2  ω     35.00 130.00   0.50    0.45    --  107.32-151.00 112.00  190
  3  ω     20.00 110.00   0.50    0.45    --   95.82-122.00 -86.00  180
  4  ω     20.00 110.00   0.50    0.45    --   95.82-122.00 -86.00  180
  5  ω     32.00 110.00   0.50    0.45    --  107.32-122.00 -86.00  156
  6  ω     81.00 112.00   0.50    0.45    --  107.32-125.00-180.00   62
  7  ω     32.00  63.00   0.50    0.45    --  107.32-125.00-180.00   62
  8  ω     11.00 103.00   0.50    0.11    --   46.11-122.00 -86.00  184
  9  ω    -36.00  26.00   0.50    0.11    --   46.11 -19.00 -90.00  124
 10  ω     25.00 105.00   0.50    0.45    --   95.82 -77.00  90.00  160
 11  ω     25.00 105.00   0.50    0.45    --   95.82 -77.00  90.00  160
 12  ω     33.00  64.00   0.50    0.45    --  107.32 -61.00  90.00   62
 13  ω     19.00  71.00   0.50    0.45    --   95.82 -61.00 -60.00  104
 14  ω     45.00 105.00   0.50    0.45    --  107.32 -77.00 -90.00  120
 15  ω     41.00 103.00   0.50    0.45    --  107.32 -77.00-180.00  124
 16  ω     15.00  51.00   0.50    0.45    --   95.82 -45.00-180.00   72
 17  ω     15.00  51.00   0.50    0.45    --   95.82 -45.00-120.00   72
 18  ω     15.00  51.00   0.50    0.45    --   95.82 -45.00 -90.00   72
 19  ω     15.00  51.00   0.50    0.45    --   95.82 -45.00 -30.00   72
 20  ω     15.00  51.00   0.50    0.45    --   95.82 -45.00 120.00   72
 21  ω     84.00 132.00   0.50    0.45    --  107.32 125.00-150.00   96
 22  ω    141.00 167.00   0.50    0.45    --  107.32 125.00-150.00   52
 23  ω     74.00 122.00   0.50    0.11    --   46.11 125.00 120.00   96
 24  ω     57.00 118.00   0.50    0.11    --   46.11 151.00 155.00  122
 25  ω     56.00 165.00   0.50    0.45    --   95.82 151.00 155.00  218
 26  ω   -110.00 -16.00   0.50    0.45    --  -92.22 122.00  -5.00  188
 27  ω   -130.00 -26.00   0.50    0.45    --  -92.22 151.00 155.00  208
 28  ω   -124.00 -26.00   0.50    0.11    --  -47.36 151.00 155.00  196
 29  ω   -104.00 -11.00   0.50    0.11    --  -47.36 122.00  -5.00  186
 30  ω    -51.00 -11.00   0.50    0.45    --  -92.22  45.00  30.00   80
 31  ω    -35.00  -9.00   0.50    0.45    --  -92.22  30.00 150.00   52
 32  ω    -51.00 -11.00   0.50    0.45    --  -92.22  45.00 -60.00   80
 33  ω    -51.00 -11.00   0.50    0.45    --  -92.22  45.00-180.00   80
 34  ω    -35.00  -9.00   0.50    0.45    --  -92.22  30.00-150.00   52
 35  ω    -35.00  -9.00   0.50    0.45    --  -92.22  30.00-120.00   52
 36  ω    -26.00  35.00   0.50    0.11    --  -47.36  19.00-120.00  122
 37  ω    -35.00  -9.00   0.50    0.45    --  -92.22  30.00 120.00   52
 38  ω    -26.00  35.00   0.50    0.11    --  -47.36  19.00 120.00  122
 39  ω   -119.00 -56.00   0.50    0.11    --  -47.36-151.00 112.00  126
 40  ω   -165.00 -55.00   0.50    0.45    --  -92.22-151.00 112.00  220
 41  ω   -168.00 -75.00   0.50    0.45    --  -92.22-122.00 -86.00  186
 42  ω   -169.00 -67.00   0.50    0.45    --  -92.22 -61.00-180.00  204
 43  ω   -169.00 -67.00   0.50    0.45    --  -92.22 -61.00-180.00  204
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'XtaLAB Synergy, Single source at home/near, HyPix-Arc 100'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0158259000
_diffrn_orient_matrix_UB_12      -0.0787785000
_diffrn_orient_matrix_UB_13      -0.1055421000
_diffrn_orient_matrix_UB_21      -0.0504818000
_diffrn_orient_matrix_UB_22      -0.1688254000
_diffrn_orient_matrix_UB_23      0.1098462000
_diffrn_orient_matrix_UB_31      -0.2369645000
_diffrn_orient_matrix_UB_32      0.1067795000
_diffrn_orient_matrix_UB_33      0.0156322000
_diffrn_oxdiff_digest_frames     
;
0171bd6a42202ab6afe001247ed0c929fa0541284cf
;
_diffrn_oxdiff_digest_hkl        
;
01d665dfaac8a1930dec29c507afef54d4ac95
;
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1790
_reflns_number_total             2050
_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 1.171.43.126a (Rigaku OD, 2024)'
_computing_data_collection       'CrysAlisPro 1.171.43.126a (Rigaku OD, 2024)'
_computing_data_reduction        'CrysAlisPro 1.171.43.126a (Rigaku OD, 2024)'
_computing_molecular_graphics    'Olex2 1.5-ac5-023 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-ac5-023 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.174
_refine_diff_density_min         -0.232
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     146
_refine_ls_number_reflns         2050
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0428
_refine_ls_R_factor_gt           0.0386
_refine_ls_restrained_S_all      1.082
_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)+(0.0627P)²+0.0859P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1099
_refine_ls_wR_factor_ref         0.1139
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C7(H7), C8(H8)
2.c Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C)
;
_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 0.60339(15) 0.96107(12) 0.67385(9) 0.0389(3) Uani 1 1 d . . . . .
O2 O 0.46658(15) 0.75221(12) 0.83970(9) 0.0377(3) Uani 1 1 d . . . . .
O3 O 0.95875(15) 0.01783(12) 0.26572(10) 0.0413(3) Uani 1 1 d . . . . .
O4 O 1.05448(17) 0.22141(14) 0.09107(10) 0.0445(3) Uani 1 1 d . . . . .
N1 N 0.97905(16) 0.17346(14) 0.20973(11) 0.0325(3) Uani 1 1 d . . . . .
C1 C 0.90866(17) 0.30858(16) 0.28886(13) 0.0278(3) Uani 1 1 d . . . . .
C2 C 0.91764(19) 0.48901(17) 0.22506(13) 0.0315(3) Uani 1 1 d . . . . .
H2 H 0.967638 0.525214 0.131751 0.038 Uiso 1 1 calc R U . . .
C3 C 0.85190(19) 0.61457(16) 0.30091(13) 0.0315(3) Uani 1 1 d . . . . .
H3 H 0.856680 0.738852 0.259039 0.038 Uiso 1 1 calc R U . . .
C4 C 0.77870(17) 0.56204(16) 0.43775(12) 0.0281(3) Uani 1 1 d . . . . .
C5 C 0.77228(18) 0.37758(17) 0.49862(13) 0.0300(3) Uani 1 1 d . . . . .
H5 H 0.722953 0.340171 0.591930 0.036 Uiso 1 1 calc R U . . .
C6 C 0.83682(18) 0.25036(16) 0.42430(13) 0.0290(3) Uani 1 1 d . . . . .
H6 H 0.831987 0.125934 0.465211 0.035 Uiso 1 1 calc R U . . .
C7 C 0.71418(18) 0.69994(16) 0.51439(13) 0.0294(3) Uani 1 1 d . . . . .
H7 H 0.737335 0.817631 0.469024 0.035 Uiso 1 1 calc R U . . .
C8 C 0.62590(19) 0.67097(17) 0.64250(13) 0.0317(3) Uani 1 1 d . . . . .
H8 H 0.599820 0.554643 0.688975 0.038 Uiso 1 1 calc R U . . .
C9 C 0.56630(18) 0.81389(16) 0.71600(12) 0.0301(3) Uani 1 1 d . . . . .
C10 C 0.4013(2) 0.86916(18) 0.92989(14) 0.0411(3) Uani 1 1 d . . . . .
H10A H 0.263197 0.962941 0.918372 0.049 Uiso 1 1 calc R U . . .
H10B H 0.505862 0.935359 0.911889 0.049 Uiso 1 1 calc R U . . .
C11 C 0.3854(3) 0.7461(2) 1.06680(15) 0.0466(4) Uani 1 1 d . . . . .
H11A H 0.524687 0.658877 1.078631 0.070 Uiso 1 1 calc R U . . .
H11B H 0.287493 0.676073 1.081723 0.070 Uiso 1 1 calc R U . . .
H11C H 0.333332 0.821826 1.130674 0.070 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 C9 1.2030(15) . ?
O2 C9 1.3345(15) . ?
O2 C10 1.4494(15) . ?
O3 N1 1.2249(14) . ?
O4 N1 1.2249(15) . ?
N1 C1 1.4662(15) . ?
C1 C2 1.3871(17) . ?
C1 C6 1.3820(17) . ?
C2 C3 1.3809(17) . ?
C3 C4 1.3927(18) . ?
C4 C5 1.4072(17) . ?
C4 C7 1.4697(16) . ?
C5 C6 1.3804(17) . ?
C7 C8 1.3243(18) . ?
C8 C9 1.4841(16) . ?
C10 C11 1.481(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
C9 O2 C10 117.81(10) . . ?
O3 N1 O4 123.16(11) . . ?
O3 N1 C1 118.20(11) . . ?
O4 N1 C1 118.65(10) . . ?
C2 C1 N1 118.79(11) . . ?
C6 C1 N1 118.49(11) . . ?
C6 C1 C2 122.72(11) . . ?
C3 C2 C1 118.18(12) . . ?
C2 C3 C4 121.10(11) . . ?
C3 C4 C5 118.92(11) . . ?
C3 C4 C7 119.01(11) . . ?
C5 C4 C7 122.06(12) . . ?
C6 C5 C4 120.76(12) . . ?
C5 C6 C1 118.32(11) . . ?
C8 C7 C4 124.33(12) . . ?
C7 C8 C9 122.30(12) . . ?
O1 C9 O2 124.39(11) . . ?
O1 C9 C8 126.54(12) . . ?
O2 C9 C8 109.06(10) . . ?
O2 C10 C11 107.38(11) . . ?

_shelx_SHELXL_version_number     2019/1
_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 1.962
_oxdiff_exptl_absorpt_empirical_full_min 0.699
####################################################################### 
# 
# 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_jds250003_fa_IV
_database_code_depnum_ccdc_archive 'CCDC 2514198'
loop_
_audit_author_name
_audit_author_address
'Paul Waddell'
;Newcastle University
United Kingdom
;
_audit_update_record             
;
2025-12-08 deposited with the CCDC.	2026-02-09 downloaded from the CCDC.
;
_audit_creation_date             2025-04-22
_audit_creation_method           
;
Olex2 1.5-ac5-023
(compiled 2022.04.12 svn.rca3783a0 for Rigaku Oxford Diffraction, GUI svn.r6498)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H22 N2 O4'
_chemical_formula_sum            'C22 H22 N2 O4'
_chemical_formula_weight         378.41
_chemical_absolute_configuration unk
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C22 H22 N2 O4'
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                   8.8556(2)
_cell_length_b                   10.0594(3)
_cell_length_c                   21.7173(6)
_cell_angle_alpha                90
_cell_angle_beta                 98.001(3)
_cell_angle_gamma                90
_cell_volume                     1915.79(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    10930
_cell_measurement_temperature    150.0(2)
_cell_measurement_theta_max      76.3170
_cell_measurement_theta_min      2.0390
_shelx_estimated_absorpt_T_max   0.995
_shelx_estimated_absorpt_T_min   0.812
_exptl_absorpt_coefficient_mu    0.742
_exptl_absorpt_correction_T_max  0.995
_exptl_absorpt_correction_T_min  0.895
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.126a (Rigaku Oxford Diffraction, 2024)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.312
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             800
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 0 1 0.0028
0 0 -1 0.0040
0 -1 0 0.0377
0 1 0 0.0427
-1 0 0 0.1391
1 0 0 0.1491
-1 -1 0 0.1094
1 1 0 0.1154
1 -1 0 0.1279
-1 1 0 0.1245

_exptl_crystal_size_max          0.292
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.007
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
0.0001 -0.0006 1.0006 -0.0564 0.0442 0.0018
-0.0001 0.0006 -1.0006 0.0564 -0.0442 -0.0018
-0.0008 -1.0000 -0.0020 0.0944 0.1206 -0.0053
0.0008 1.0000 0.0020 -0.0944 -0.1206 0.0053
-0.9994 0.0001 0.0002 0.0266 -0.0130 0.1730
0.9994 -0.0001 -0.0002 -0.0266 0.0130 -0.1730
-1.0002 -0.9999 -0.0018 0.1210 0.1076 0.1677
1.0002 0.9999 0.0018 -0.1210 -0.1076 -0.1677
0.9986 -1.0001 -0.0022 0.0678 0.1336 -0.1783
-0.9986 1.0001 0.0022 -0.0678 -0.1336 0.1783

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0405
_diffrn_reflns_av_unetI/netI     0.0422
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.920
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            22630
_diffrn_reflns_point_group_measured_fraction_full 0.980
_diffrn_reflns_point_group_measured_fraction_max 0.884
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.046
_diffrn_reflns_theta_min         2.054
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.0(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            'HyPix-Arc 100'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.920
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     72.00  97.00   0.50    1.27    --   46.11 130.00  87.00   50
  2  ω     69.00  94.00   0.50    1.27    --   46.11 140.00 -98.00   50
  3  ω     40.00  84.00   0.50    1.27    --   46.11-130.00  16.00   88
  4  ω    -87.00 -62.00   0.50    1.27    --  -47.36 130.00  87.00   50
  5  ω   -119.00 -90.00   0.50    5.07    --  -92.22-130.00  16.00   58
  6  ω   -140.00-115.00   0.50    5.07    --  -92.22-140.00-157.00   50
  7  ω    -73.00 -36.00   0.50    5.07    --  -92.22 140.00 -98.00   74
  8  ω   -115.00 -51.00   0.50    5.07    --  -92.22 130.00  87.00  128
  9  ω     48.00  73.00   0.50    5.07    --   95.82-140.00-157.00   50
 10  ω     21.00 115.00   0.50    5.07    --   95.82-130.00  16.00  188
 11  ω     49.00  74.00   0.50    5.07    --  107.32-130.00  16.00   50
 12  ω     66.00 172.00   0.50    5.07    --  107.32 140.00 -98.00  212
 13  ω     53.00  78.00   0.50    5.07    --  107.32-140.00-157.00   50
 14  ω    -34.00  24.00   0.50    1.27    --   46.11 -19.00   0.00  116
 15  ω    -36.00  13.00   0.50    1.27    --   46.11 -19.00  60.00   98
 16  ω     78.00 103.00   0.50    1.27    --   46.11 125.00 -60.00   50
 17  ω   -120.00 -73.00   0.50    1.27    --  -47.36-125.00-120.00   94
 18  ω    -37.00  33.00   0.50    1.27    --  -47.36  38.00-180.00  140
 19  ω    -35.00  -9.00   0.50    5.07    --  -92.22  30.00  30.00   52
 20  ω   -168.00-122.00   0.50    5.07    --  -92.22-125.00 150.00   92
 21  ω    -35.00  -9.00   0.50    5.07    --  -92.22  30.00  90.00   52
 22  ω    -51.00 -16.00   0.50    5.07    --  -92.22  45.00-150.00   70
 23  ω    -45.00 -19.00   0.50    5.07    --  -92.22  45.00  90.00   52
 24  ω    -51.00 -11.00   0.50    5.07    --  -92.22  45.00-120.00   80
 25  ω    -34.00  -9.00   0.50    5.07    --  -92.22  30.00  60.00   50
 26  ω   -117.00 -87.00   0.50    5.07    --  -92.22-125.00 150.00   60
 27  ω    -34.00  -9.00   0.50    5.07    --  -92.22  30.00 150.00   50
 28  ω     16.00  43.00   0.50    5.07    --   95.82 -45.00 -30.00   54
 29  ω     15.00  40.00   0.50    5.07    --   95.82 -45.00   0.00   50
 30  ω     33.00  71.00   0.50    5.07    --   95.82 -61.00  30.00   76
 31  ω     45.00  71.00   0.50    5.07    --  107.32 -95.00-150.00   52
 32  ω     34.00  79.00   0.50    5.07    --  107.32-125.00 -90.00   90
 33  ω     74.00 103.00   0.50    5.07    --  107.32 -95.00-150.00   58
 34  ω     45.00  71.00   0.50    1.27    --   46.11-140.00-157.00   52
 35  ω    -11.00  19.00   0.50    1.27    --   46.11 -19.00-150.00   60
 36  ω     80.00 122.00   0.50    1.27    --   46.11 125.00  30.00   84
 37  ω    -23.00  16.00   0.50    1.27    --   46.11 -19.00-180.00   78
 38  ω   -102.00 -73.00   0.50    1.27    --  -47.36-125.00  90.00   58
 39  ω    -94.00 -64.00   0.50    5.07    --  -92.22 -77.00  90.00   60
 40  ω    -35.00 -10.00   0.50    5.07    --  -92.22  30.00   0.00   50
 41  ω   -147.00-119.00   0.50    5.07    --  -92.22 -77.00  90.00   56
 42  ω    -41.00 -15.00   0.50    5.07    --  -92.22  45.00 -60.00   52
 43  ω    -35.00 -10.00   0.50    5.07    --  -92.22  30.00 -30.00   50
 44  ω    -35.00 -10.00   0.50    5.07    --  -92.22  30.00-180.00   50
 45  ω    -35.00 -10.00   0.50    5.07    --  -92.22  30.00 120.00   50
 46  ω    -54.00 -21.00   0.50    5.07    --  -92.22 125.00 -30.00   66
 47  ω    -38.00 -12.00   0.50    5.07    --  -92.22  45.00 120.00   52
 48  ω   -111.00 -60.00   0.50    5.07    --  -92.22 125.00 -30.00  102
 49  ω    -87.00 -61.00   0.50    5.07    --  -92.22 -77.00 -90.00   52
 50  ω   -144.00-113.00   0.50    5.07    --  -92.22 -77.00 -90.00   62
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'XtaLAB Synergy, Single source at home/near, HyPix-Arc 100'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0266254000
_diffrn_orient_matrix_UB_12      -0.0942306000
_diffrn_orient_matrix_UB_13      -0.0564163000
_diffrn_orient_matrix_UB_21      0.0129878000
_diffrn_orient_matrix_UB_22      -0.1206707000
_diffrn_orient_matrix_UB_23      0.0441080000
_diffrn_orient_matrix_UB_31      -0.1731100000
_diffrn_orient_matrix_UB_32      0.0054411000
_diffrn_orient_matrix_UB_33      0.0018242000
_diffrn_oxdiff_digest_frames     
;
010e41379c47f69791521737a0a8acb0cf03568816c
;
_diffrn_oxdiff_digest_hkl        
;
012a90aea3537fb6f85eba556444c145250b62
;
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.814
_reflns_Friedel_fraction_full    0.960
_reflns_Friedel_fraction_max     0.844
_reflns_number_gt                6538
_reflns_number_total             7157
_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 1.171.43.126a (Rigaku OD, 2024)'
_computing_data_collection       
'CrysAlisPro system (CCD 43.126a 64-bit (release 11-06-2024))'
_computing_data_reduction        'CrysAlisPro 1.171.43.126a (Rigaku OD, 2024)'
_computing_molecular_graphics    'Olex2 1.5-ac5-023 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-ac5-023 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.346
_refine_diff_density_min         -0.188
_refine_diff_density_rms         0.038
_refine_ls_abs_structure_details 
;
 Flack x determined using 2695 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.39(9)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     509
_refine_ls_number_reflns         7157
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0420
_refine_ls_R_factor_gt           0.0378
_refine_ls_restrained_S_all      1.031
_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)+(0.0612P)²+0.1261P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0980
_refine_ls_wR_factor_ref         0.1006
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C21(H21A,H21B), C32(H32A,H32B), C43(H43A,H43B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C7(H7), C8(H8), C13(H13), C14(H14), C16(H16),
 C17(H17), C18(H18), C19(H19), C24(H24), C25(H25), C27(H27), C28(H28), C29(H29),
  C30(H30), C35(H35), C36(H36), C38(H38), C39(H39), C40(H40), C41(H41)
2.c Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C22(H22A,H22B,H22C), C33(H33A,H33B,H33C), C44(H44A,H44B,
 H44C)
;
_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 1.43504(19) 0.39513(18) 0.80449(8) 0.0321(4) Uani 1 1 d . . . . .
O2 O 1.5345(2) 0.60061(18) 0.80452(8) 0.0305(4) Uani 1 1 d . . . . .
O3 O 0.1493(2) 0.5125(2) 0.11058(10) 0.0481(5) Uani 1 1 d . . . . .
O4 O 0.2178(2) 0.72063(18) 0.08958(8) 0.0340(4) Uani 1 1 d . . . . .
O5 O -0.0388(3) 0.6389(2) 0.24226(10) 0.0493(6) Uani 1 1 d . . . . .
O6 O -0.1351(2) 0.43255(18) 0.23206(9) 0.0339(4) Uani 1 1 d . . . . .
O7 O 1.2691(2) 0.5110(2) 0.92140(9) 0.0390(4) Uani 1 1 d . . . . .
O8 O 1.2712(2) 0.28738(18) 0.91651(8) 0.0333(4) Uani 1 1 d . . . . .
N1 N 0.8405(2) 0.5620(2) 0.46949(10) 0.0281(5) Uani 1 1 d . . . . .
N2 N 0.7640(2) 0.4634(2) 0.44685(10) 0.0285(5) Uani 1 1 d . . . . .
N3 N 0.5139(2) 0.4596(2) 0.58346(10) 0.0266(4) Uani 1 1 d . . . . .
N4 N 0.5919(2) 0.5578(2) 0.60488(10) 0.0284(5) Uani 1 1 d . . . . .
C1 C 0.9343(3) 0.5336(2) 0.52680(11) 0.0245(5) Uani 1 1 d . . . . .
C2 C 0.9246(3) 0.4174(2) 0.56162(11) 0.0261(5) Uani 1 1 d . . . . .
H2 H 0.850397 0.351697 0.547951 0.031 Uiso 1 1 calc R U . . .
C3 C 1.0234(3) 0.3990(3) 0.61581(11) 0.0256(5) Uani 1 1 d . . . . .
H3 H 1.016892 0.319620 0.639017 0.031 Uiso 1 1 calc R U . . .
C4 C 1.1333(3) 0.4943(2) 0.63751(11) 0.0249(5) Uani 1 1 d . . . . .
C5 C 1.1395(3) 0.6115(2) 0.60295(11) 0.0264(5) Uani 1 1 d . . . . .
H5 H 1.211556 0.678513 0.617206 0.032 Uiso 1 1 calc R U . . .
C6 C 1.0418(3) 0.6302(2) 0.54846(11) 0.0272(5) Uani 1 1 d . . . . .
H6 H 1.047684 0.709756 0.525366 0.033 Uiso 1 1 calc R U . . .
C7 C 1.2359(3) 0.4674(3) 0.69524(11) 0.0264(5) Uani 1 1 d . . . . .
H7 H 1.222680 0.384687 0.714915 0.032 Uiso 1 1 calc R U . . .
C8 C 1.3455(3) 0.5464(3) 0.72306(12) 0.0285(5) Uani 1 1 d . . . . .
H8 H 1.362756 0.630650 0.705545 0.034 Uiso 1 1 calc R U . . .
C9 C 1.4401(3) 0.5035(3) 0.78097(11) 0.0269(5) Uani 1 1 d . . . . .
C10 C 1.6276(3) 0.5703(3) 0.86336(12) 0.0335(6) Uani 1 1 d . . . . .
H10A H 1.691443 0.491045 0.858905 0.040 Uiso 1 1 calc R U . . .
H10B H 1.561854 0.551687 0.895661 0.040 Uiso 1 1 calc R U . . .
C11 C 1.7269(3) 0.6891(3) 0.88152(13) 0.0377(6) Uani 1 1 d . . . . .
H11A H 1.790827 0.707078 0.849083 0.057 Uiso 1 1 calc R U . . .
H11B H 1.792016 0.671045 0.920923 0.057 Uiso 1 1 calc R U . . .
H11C H 1.662594 0.766624 0.886394 0.057 Uiso 1 1 calc R U . . .
C12 C 0.6705(3) 0.4879(2) 0.38939(11) 0.0257(5) Uani 1 1 d . . . . .
C13 C 0.6743(3) 0.6039(3) 0.35353(12) 0.0271(5) Uani 1 1 d . . . . .
H13 H 0.742606 0.673826 0.367536 0.033 Uiso 1 1 calc R U . . .
C14 C 0.5786(3) 0.6161(3) 0.29792(11) 0.0282(5) Uani 1 1 d . . . . .
H14 H 0.581841 0.694644 0.273853 0.034 Uiso 1 1 calc R U . . .
C15 C 0.4765(3) 0.5141(3) 0.27647(11) 0.0265(5) Uani 1 1 d . . . . .
C16 C 0.4760(3) 0.3988(3) 0.31264(12) 0.0296(5) Uani 1 1 d . . . . .
H16 H 0.408849 0.328174 0.298450 0.035 Uiso 1 1 calc R U . . .
C17 C 0.5705(3) 0.3854(2) 0.36829(12) 0.0280(5) Uani 1 1 d . . . . .
H17 H 0.567660 0.306567 0.392197 0.034 Uiso 1 1 calc R U . . .
C18 C 0.3686(3) 0.5212(3) 0.21896(12) 0.0300(5) Uani 1 1 d . . . . .
H18 H 0.304686 0.445818 0.209906 0.036 Uiso 1 1 calc R U . . .
C19 C 0.3488(3) 0.6198(3) 0.17779(12) 0.0295(5) Uani 1 1 d . . . . .
H19 H 0.411236 0.696926 0.183261 0.035 Uiso 1 1 calc R U . . .
C20 C 0.2291(3) 0.6083(3) 0.12356(13) 0.0323(6) Uani 1 1 d . . . . .
C21 C 0.1052(3) 0.7199(3) 0.03413(13) 0.0382(6) Uani 1 1 d . . . . .
H21A H 0.003047 0.698681 0.045060 0.046 Uiso 1 1 calc R U . . .
H21B H 0.131884 0.652398 0.004282 0.046 Uiso 1 1 calc R U . . .
C22 C 0.1053(4) 0.8560(4) 0.00609(16) 0.0521(8) Uani 1 1 d . . . . .
H22A H 0.028016 0.860418 -0.030817 0.078 Uiso 1 1 calc R U . . .
H22B H 0.205996 0.874592 -0.005813 0.078 Uiso 1 1 calc R U . . .
H22C H 0.082082 0.922139 0.036565 0.078 Uiso 1 1 calc R U . . .
C23 C 0.4186(3) 0.4888(2) 0.52653(11) 0.0252(5) Uani 1 1 d . . . . .
C24 C 0.4344(3) 0.6046(3) 0.49191(11) 0.0263(5) Uani 1 1 d . . . . .
H24 H 0.508723 0.669376 0.506728 0.032 Uiso 1 1 calc R U . . .
C25 C 0.3417(3) 0.6235(3) 0.43641(11) 0.0268(5) Uani 1 1 d . . . . .
H25 H 0.353286 0.701693 0.413021 0.032 Uiso 1 1 calc R U . . .
C26 C 0.2307(3) 0.5305(2) 0.41351(11) 0.0252(5) Uani 1 1 d . . . . .
C27 C 0.2146(3) 0.4163(3) 0.44910(11) 0.0269(5) Uani 1 1 d . . . . .
H27 H 0.138058 0.352832 0.434970 0.032 Uiso 1 1 calc R U . . .
C28 C 0.3091(3) 0.3951(2) 0.50464(11) 0.0260(5) Uani 1 1 d . . . . .
H28 H 0.299004 0.316229 0.527783 0.031 Uiso 1 1 calc R U . . .
C29 C 0.1374(3) 0.5566(3) 0.35355(12) 0.0279(5) Uani 1 1 d . . . . .
H29 H 0.157926 0.637648 0.333838 0.033 Uiso 1 1 calc R U . . .
C30 C 0.0283(3) 0.4820(3) 0.32322(12) 0.0298(6) Uani 1 1 d . . . . .
H30 H 0.000470 0.400131 0.340325 0.036 Uiso 1 1 calc R U . . .
C31 C -0.0498(3) 0.5282(3) 0.26227(13) 0.0313(6) Uani 1 1 d . . . . .
C32 C -0.2162(3) 0.4694(3) 0.17158(13) 0.0379(6) Uani 1 1 d . . . . .
H32A H -0.142768 0.492093 0.142743 0.045 Uiso 1 1 calc R U . . .
H32B H -0.281706 0.547776 0.175608 0.045 Uiso 1 1 calc R U . . .
C33 C -0.3115(4) 0.3531(3) 0.14727(15) 0.0454(7) Uani 1 1 d . . . . .
H33A H -0.371490 0.376646 0.107389 0.068 Uiso 1 1 calc R U . . .
H33B H -0.380334 0.328962 0.177097 0.068 Uiso 1 1 calc R U . . .
H33C H -0.245102 0.277579 0.141393 0.068 Uiso 1 1 calc R U . . .
C34 C 0.6941(3) 0.5347(2) 0.65985(11) 0.0248(5) Uani 1 1 d . . . . .
C35 C 0.7041(3) 0.4175(3) 0.69544(11) 0.0264(5) Uani 1 1 d . . . . .
H35 H 0.636209 0.345799 0.684050 0.032 Uiso 1 1 calc R U . . .
C36 C 0.8132(3) 0.4077(3) 0.74691(11) 0.0256(5) Uani 1 1 d . . . . .
H36 H 0.821261 0.327744 0.770410 0.031 Uiso 1 1 calc R U . . .
C37 C 0.9126(3) 0.5132(3) 0.76542(11) 0.0264(5) Uani 1 1 d . . . . .
C38 C 0.8983(3) 0.6304(2) 0.73054(12) 0.0277(5) Uani 1 1 d . . . . .
H38 H 0.962755 0.703907 0.743028 0.033 Uiso 1 1 calc R U . . .
C39 C 0.7914(3) 0.6404(2) 0.67819(11) 0.0276(5) Uani 1 1 d . . . . .
H39 H 0.784051 0.719979 0.654437 0.033 Uiso 1 1 calc R U . . .
C40 C 1.0317(3) 0.5061(3) 0.81907(11) 0.0277(5) Uani 1 1 d . . . . .
H40 H 1.073450 0.588308 0.834866 0.033 Uiso 1 1 calc R U . . .
C41 C 1.0879(3) 0.3966(3) 0.84819(11) 0.0284(5) Uani 1 1 d . . . . .
H41 H 1.045145 0.312181 0.836524 0.034 Uiso 1 1 calc R U . . .
C42 C 1.2172(3) 0.4076(3) 0.89876(11) 0.0294(5) Uani 1 1 d . . . . .
C43 C 1.4083(3) 0.2859(3) 0.96178(13) 0.0391(6) Uani 1 1 d . . . . .
H43A H 1.388250 0.326995 1.001275 0.047 Uiso 1 1 calc R U . . .
H43B H 1.490995 0.336119 0.945922 0.047 Uiso 1 1 calc R U . . .
C44 C 1.4525(3) 0.1434(3) 0.97184(14) 0.0431(7) Uani 1 1 d . . . . .
H44A H 1.476880 0.105309 0.932865 0.065 Uiso 1 1 calc R U . . .
H44B H 1.367642 0.094065 0.985464 0.065 Uiso 1 1 calc R U . . .
H44C H 1.542034 0.137259 1.003786 0.065 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 C9 1.208(3) . ?
O2 C9 1.340(3) . ?
O2 C10 1.454(3) . ?
O3 C20 1.205(3) . ?
O4 C20 1.346(3) . ?
O4 C21 1.453(3) . ?
O5 C31 1.204(3) . ?
O6 C31 1.338(3) . ?
O6 C32 1.454(3) . ?
O7 C42 1.213(3) . ?
O8 C42 1.338(3) . ?
O8 C43 1.452(3) . ?
N1 N2 1.262(3) . ?
N1 C1 1.426(3) . ?
N2 C12 1.420(3) . ?
N3 N4 1.257(3) . ?
N3 C23 1.428(3) . ?
N4 C34 1.413(3) . ?
C1 C2 1.401(3) . ?
C1 C6 1.395(4) . ?
C2 C3 1.378(3) . ?
C3 C4 1.401(3) . ?
C4 C5 1.403(3) . ?
C4 C7 1.467(3) . ?
C5 C6 1.378(3) . ?
C7 C8 1.332(4) . ?
C8 C9 1.475(3) . ?
C10 C11 1.503(4) . ?
C12 C13 1.406(3) . ?
C12 C17 1.394(4) . ?
C13 C14 1.381(3) . ?
C14 C15 1.404(4) . ?
C15 C16 1.401(4) . ?
C15 C18 1.465(3) . ?
C16 C17 1.378(3) . ?
C18 C19 1.331(4) . ?
C19 C20 1.476(3) . ?
C21 C22 1.499(4) . ?
C23 C24 1.404(4) . ?
C23 C28 1.388(4) . ?
C24 C25 1.374(3) . ?
C25 C26 1.397(4) . ?
C26 C27 1.403(4) . ?
C26 C29 1.465(3) . ?
C27 C28 1.386(3) . ?
C29 C30 1.324(4) . ?
C30 C31 1.480(3) . ?
C32 C33 1.495(4) . ?
C34 C35 1.405(3) . ?
C34 C39 1.391(3) . ?
C35 C36 1.375(3) . ?
C36 C37 1.402(4) . ?
C37 C38 1.398(4) . ?
C37 C40 1.460(3) . ?
C38 C39 1.378(3) . ?
C40 C41 1.332(4) . ?
C41 C42 1.477(3) . ?
C43 C44 1.495(4) . ?

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
C9 O2 C10 115.5(2) . . ?
C20 O4 C21 116.1(2) . . ?
C31 O6 C32 115.7(2) . . ?
C42 O8 C43 115.8(2) . . ?
N2 N1 C1 113.5(2) . . ?
N1 N2 C12 114.9(2) . . ?
N4 N3 C23 112.7(2) . . ?
N3 N4 C34 116.0(2) . . ?
C2 C1 N1 124.5(2) . . ?
C6 C1 N1 116.2(2) . . ?
C6 C1 C2 119.3(2) . . ?
C3 C2 C1 119.6(2) . . ?
C2 C3 C4 121.6(2) . . ?
C3 C4 C5 118.2(2) . . ?
C3 C4 C7 118.6(2) . . ?
C5 C4 C7 123.2(2) . . ?
C6 C5 C4 120.5(2) . . ?
C5 C6 C1 120.8(2) . . ?
C8 C7 C4 127.0(2) . . ?
C7 C8 C9 120.2(2) . . ?
O1 C9 O2 123.7(2) . . ?
O1 C9 C8 125.1(2) . . ?
O2 C9 C8 111.2(2) . . ?
O2 C10 C11 107.7(2) . . ?
C13 C12 N2 125.1(2) . . ?
C17 C12 N2 115.2(2) . . ?
C17 C12 C13 119.7(2) . . ?
C14 C13 C12 120.0(2) . . ?
C13 C14 C15 120.9(2) . . ?
C14 C15 C18 124.1(2) . . ?
C16 C15 C14 118.1(2) . . ?
C16 C15 C18 117.8(2) . . ?
C17 C16 C15 121.6(2) . . ?
C16 C17 C12 119.7(2) . . ?
C19 C18 C15 128.2(2) . . ?
C18 C19 C20 119.4(2) . . ?
O3 C20 O4 123.2(2) . . ?
O3 C20 C19 125.6(3) . . ?
O4 C20 C19 111.2(2) . . ?
O4 C21 C22 107.0(2) . . ?
C24 C23 N3 123.0(2) . . ?
C28 C23 N3 117.2(2) . . ?
C28 C23 C24 119.8(2) . . ?
C25 C24 C23 119.5(2) . . ?
C24 C25 C26 121.7(2) . . ?
C25 C26 C27 118.2(2) . . ?
C25 C26 C29 118.6(2) . . ?
C27 C26 C29 123.2(2) . . ?
C28 C27 C26 120.7(2) . . ?
C27 C28 C23 120.1(2) . . ?
C30 C29 C26 128.5(2) . . ?
C29 C30 C31 119.0(2) . . ?
O5 C31 O6 123.8(2) . . ?
O5 C31 C30 124.2(2) . . ?
O6 C31 C30 112.0(2) . . ?
O6 C32 C33 107.6(2) . . ?
C35 C34 N4 125.9(2) . . ?
C39 C34 N4 114.5(2) . . ?
C39 C34 C35 119.6(2) . . ?
C36 C35 C34 119.4(2) . . ?
C35 C36 C37 121.4(2) . . ?
C36 C37 C40 123.2(2) . . ?
C38 C37 C36 118.5(2) . . ?
C38 C37 C40 118.3(2) . . ?
C39 C38 C37 120.6(2) . . ?
C38 C39 C34 120.5(2) . . ?
C41 C40 C37 126.9(2) . . ?
C40 C41 C42 119.4(2) . . ?
O7 C42 O8 124.0(2) . . ?
O7 C42 C41 125.2(2) . . ?
O8 C42 C41 110.8(2) . . ?
O8 C43 C44 106.6(2) . . ?

_shelx_SHELXL_version_number     2019/1
_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 1.856
_oxdiff_exptl_absorpt_empirical_full_min 0.622
