# Supplementary Information (SI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2025

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_gwg23jc01_auto
_database_code_depnum_ccdc_archive 'CCDC 2390183'
loop_
_audit_author_name
_audit_author_address
'Jack Clegg'
;The University of Queensalnd
Australia
;
_audit_update_record             
;
2024-10-11 deposited with the CCDC.	2024-11-27 downloaded from the CCDC.
;
_audit_creation_date             2024-10-11
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.01.12 svn.r2f8d729c for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C26 H15 N O5'
_chemical_formula_sum            'C26 H15 N O5'
_chemical_formula_weight         421.39
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C26 H15 N O5'
_chemical_oxdiff_usercomment     'oidb - dark crystal'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   14.885(2)
_cell_length_b                   9.4476(11)
_cell_length_c                   15.911(2)
_cell_angle_alpha                90
_cell_angle_beta                 116.173(19)
_cell_angle_gamma                90
_cell_volume                     2008.0(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1973
_cell_measurement_temperature    190(2)
_cell_measurement_theta_max      24.8650
_cell_measurement_theta_min      2.9110
_shelx_estimated_absorpt_T_max   0.995
_shelx_estimated_absorpt_T_min   0.953
_exptl_absorpt_coefficient_mu    0.098
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.90826
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.123a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            violet
_exptl_crystal_colour_primary    violet
_exptl_crystal_density_diffrn    1.394
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             872
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0527
_diffrn_reflns_av_unetI/netI     0.0714
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            8881
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.121
_diffrn_reflns_theta_max         25.121
_diffrn_reflns_theta_min         2.641
_diffrn_ambient_temperature      190(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0217
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -30.00  35.00   1.00    5.00    --   19.52 -57.00-150.00   65
  2  ω     17.00  46.00   1.00    5.00    --   19.52 -77.00 120.00   29
  3  ω     12.00  38.00   1.00    5.00    --   19.52  77.00-180.00   26
  4  ω    -84.00  -4.00   1.00    5.00    --  -20.93 -57.00 -60.00   80
  5  ω    -32.00  31.00   1.00    5.00    --  -20.93  57.00  60.00   63
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, EosS2, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0117680000
_diffrn_orient_matrix_UB_12      0.0366033000
_diffrn_orient_matrix_UB_13      0.0328649000
_diffrn_orient_matrix_UB_21      0.0442077000
_diffrn_orient_matrix_UB_22      0.0409811000
_diffrn_orient_matrix_UB_23      0.0139388000
_diffrn_orient_matrix_UB_31      -0.0269552000
_diffrn_orient_matrix_UB_32      0.0511567000
_diffrn_orient_matrix_UB_33      -0.0344817000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2538
_reflns_number_total             3576
_reflns_odcompleteness_completeness 99.87
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     28.22
_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 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.317
_refine_diff_density_min         -0.234
_refine_diff_density_rms         0.054
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     289
_refine_ls_number_reflns         3576
_refine_ls_number_restraints     36
_refine_ls_R_factor_all          0.0933
_refine_ls_R_factor_gt           0.0635
_refine_ls_restrained_S_all      1.055
_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)+(0.0562P)²+0.6480P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1369
_refine_ls_wR_factor_ref         0.1555
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2. Uiso/Uaniso restraints and constraints
C17 \\sim C12 \\sim C11 \\sim C14 \\sim C15 \\sim C16: within 2A with sigma of
0.02 and sigma for terminal atoms of 0.02 within 2A
3.a Ternary CH refined with riding coordinates:
 C18(H18), C9(H9)
3.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C5(H5), C6(H6), C4(H4), C7(H7), C23(H23), C26(H26), C24(H24),
 C25(H25), C14(H14), C15(H15), C17(H17), C16(H16)
;
_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 0.74056(16) 0.5231(2) 0.26963(13) 0.0410(6) Uani 1 1 d . . . . .
N1 N 0.70545(17) 0.2973(2) 0.29932(14) 0.0298(6) Uani 1 1 d . . . . .
H1 H 0.730205 0.249988 0.266653 0.036 Uiso 1 1 calc R U . . .
O3 O 0.57528(17) 0.6946(2) 0.46555(13) 0.0438(6) Uani 1 1 d . . . . .
O5 O 0.62381(18) 0.7851(2) 0.28440(14) 0.0484(6) Uani 1 1 d . . . . .
O2 O 0.85814(16) 0.4296(2) 0.50244(14) 0.0475(6) Uani 1 1 d . . . . .
O4 O 0.44406(17) 0.3531(2) 0.21067(14) 0.0492(6) Uani 1 1 d . . . . .
C1 C 0.7054(2) 0.4391(3) 0.30493(17) 0.0295(7) Uani 1 1 d . . . . .
C8 C 0.6614(2) 0.2333(3) 0.35158(17) 0.0269(6) Uani 1 1 d . . . . .
C3 C 0.6253(2) 0.3372(3) 0.39029(17) 0.0248(6) Uani 1 1 d . . . . .
C5 C 0.5750(2) 0.1584(3) 0.46486(19) 0.0347(7) Uani 1 1 d . . . . .
H5 H 0.545725 0.130889 0.504677 0.042 Uiso 1 1 calc R U . . .
C6 C 0.6104(2) 0.0558(3) 0.4249(2) 0.0391(8) Uani 1 1 d . . . . .
H6 H 0.605646 -0.041199 0.438175 0.047 Uiso 1 1 calc R U . . .
C4 C 0.5818(2) 0.2998(3) 0.44753(18) 0.0311(7) Uani 1 1 d . . . . .
H4 H 0.556901 0.370050 0.474512 0.037 Uiso 1 1 calc R U . . .
C22 C 0.5688(2) 0.6875(3) 0.24422(19) 0.0333(7) Uani 1 1 d . . . . .
C7 C 0.6528(2) 0.0923(3) 0.36574(19) 0.0331(7) Uani 1 1 d . . . . .
H7 H 0.674909 0.022207 0.336305 0.040 Uiso 1 1 calc R U . . .
C18 C 0.5489(2) 0.5564(3) 0.29006(17) 0.0280(6) Uani 1 1 d . . . . .
H18 H 0.511358 0.587701 0.325719 0.034 Uiso 1 1 calc R U . . .
C21 C 0.5091(2) 0.6759(3) 0.14204(18) 0.0318(7) Uani 1 1 d . . . . .
C2 C 0.6453(2) 0.4801(3) 0.35957(16) 0.0253(6) Uani 1 1 d . . . . .
C10 C 0.8009(2) 0.5035(3) 0.51734(18) 0.0328(7) Uani 1 1 d . . . . .
C9 C 0.7086(2) 0.5765(3) 0.44268(17) 0.0290(7) Uani 1 1 d . . . . .
H9 H 0.732427 0.657864 0.417596 0.035 Uiso 1 1 calc R U . . .
C13 C 0.6563(2) 0.6371(3) 0.49784(18) 0.0302(7) Uani 1 1 d . . . . .
C20 C 0.4548(2) 0.5498(3) 0.12062(18) 0.0321(7) Uani 1 1 d . . . . .
C19 C 0.4774(2) 0.4678(3) 0.20658(18) 0.0313(7) Uani 1 1 d . . . . .
C11 C 0.8056(2) 0.5399(4) 0.60910(18) 0.0414(8) Uani 1 1 d . U . . .
C23 C 0.3912(2) 0.5150(4) 0.02914(19) 0.0411(8) Uani 1 1 d . . . . .
H23 H 0.353573 0.429714 0.014101 0.049 Uiso 1 1 calc R U . . .
C26 C 0.5039(2) 0.7692(3) 0.0733(2) 0.0404(8) Uani 1 1 d . . . . .
H26 H 0.541654 0.854384 0.088059 0.049 Uiso 1 1 calc R U . . .
C24 C 0.3846(2) 0.6104(4) -0.0402(2) 0.0439(9) Uani 1 1 d . . . . .
H24 H 0.340545 0.590489 -0.103694 0.053 Uiso 1 1 calc R U . . .
C12 C 0.7222(2) 0.6168(4) 0.59727(19) 0.0406(8) Uani 1 1 d . U . . .
C25 C 0.4403(2) 0.7323(4) -0.0187(2) 0.0467(9) Uani 1 1 d . . . . .
H25 H 0.435445 0.793208 -0.068044 0.056 Uiso 1 1 calc R U . . .
C14 C 0.8778(3) 0.5036(5) 0.6976(2) 0.0702(12) Uani 1 1 d . U . . .
H14 H 0.935354 0.450432 0.705898 0.084 Uiso 1 1 calc R U . . .
C15 C 0.8630(4) 0.5474(6) 0.7726(2) 0.1017(18) Uani 1 1 d . U . . .
H15 H 0.911186 0.523529 0.834025 0.122 Uiso 1 1 calc R U . . .
C17 C 0.7069(3) 0.6611(5) 0.6735(2) 0.0677(12) Uani 1 1 d . U . . .
H17 H 0.649024 0.713246 0.665257 0.081 Uiso 1 1 calc R U . . .
C16 C 0.7790(4) 0.6261(6) 0.7611(2) 0.1016(19) Uani 1 1 d . U . . .
H16 H 0.771655 0.655921 0.814783 0.122 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.216(3) . ?
N1 H1 0.8800 . ?
N1 C1 1.343(4) . ?
N1 C8 1.403(3) . ?
O3 C13 1.211(3) . ?
O5 C22 1.211(3) . ?
O2 C10 1.203(3) . ?
O4 C19 1.205(3) . ?
C1 C2 1.547(4) . ?
C8 C3 1.387(4) . ?
C8 C7 1.366(4) . ?
C3 C4 1.376(4) . ?
C3 C2 1.510(4) . ?
C5 H5 0.9500 . ?
C5 C6 1.385(4) . ?
C5 C4 1.377(4) . ?
C6 H6 0.9500 . ?
C6 C7 1.388(4) . ?
C4 H4 0.9500 . ?
C22 C18 1.531(4) . ?
C22 C21 1.473(4) . ?
C7 H7 0.9500 . ?
C18 H18 1.0000 . ?
C18 C2 1.550(4) . ?
C18 C19 1.533(4) . ?
C21 C20 1.395(4) . ?
C21 C26 1.379(4) . ?
C2 C9 1.538(3) . ?
C10 C9 1.528(4) . ?
C10 C11 1.471(4) . ?
C9 H9 1.0000 . ?
C9 C13 1.519(4) . ?
C13 C12 1.460(4) . ?
C20 C19 1.476(4) . ?
C20 C23 1.381(4) . ?
C11 C12 1.378(4) . ?
C11 C14 1.386(4) . ?
C23 H23 0.9500 . ?
C23 C24 1.393(4) . ?
C26 H26 0.9500 . ?
C26 C25 1.393(4) . ?
C24 H24 0.9500 . ?
C24 C25 1.371(5) . ?
C12 C17 1.394(4) . ?
C25 H25 0.9500 . ?
C14 H14 0.9500 . ?
C14 C15 1.370(5) . ?
C15 H15 0.9500 . ?
C15 C16 1.396(6) . ?
C17 H17 0.9500 . ?
C17 C16 1.372(5) . ?
C16 H16 0.9500 . ?

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
C1 N1 H1 123.9 . . ?
C1 N1 C8 112.1(2) . . ?
C8 N1 H1 123.9 . . ?
O1 C1 N1 127.4(3) . . ?
O1 C1 C2 124.7(3) . . ?
N1 C1 C2 107.7(2) . . ?
C3 C8 N1 109.4(2) . . ?
C7 C8 N1 128.4(3) . . ?
C7 C8 C3 122.3(3) . . ?
C8 C3 C2 108.6(2) . . ?
C4 C3 C8 120.0(2) . . ?
C4 C3 C2 131.4(2) . . ?
C6 C5 H5 119.6 . . ?
C4 C5 H5 119.6 . . ?
C4 C5 C6 120.7(3) . . ?
C5 C6 H6 119.5 . . ?
C5 C6 C7 121.1(3) . . ?
C7 C6 H6 119.5 . . ?
C3 C4 H4 120.7 . . ?
C5 C4 C3 118.6(3) . . ?
C5 C4 H4 120.7 . . ?
O5 C22 C18 126.3(3) . . ?
O5 C22 C21 125.3(3) . . ?
C21 C22 C18 108.4(2) . . ?
C8 C7 C6 117.3(3) . . ?
C8 C7 H7 121.4 . . ?
C6 C7 H7 121.4 . . ?
C22 C18 H18 107.8 . . ?
C22 C18 C2 113.8(2) . . ?
C22 C18 C19 103.6(2) . . ?
C2 C18 H18 107.8 . . ?
C19 C18 H18 107.8 . . ?
C19 C18 C2 115.7(2) . . ?
C20 C21 C22 109.6(2) . . ?
C26 C21 C22 128.5(3) . . ?
C26 C21 C20 121.9(3) . . ?
C1 C2 C18 107.4(2) . . ?
C3 C2 C1 101.7(2) . . ?
C3 C2 C18 113.2(2) . . ?
C3 C2 C9 112.6(2) . . ?
C9 C2 C1 110.1(2) . . ?
C9 C2 C18 111.2(2) . . ?
O2 C10 C9 125.5(2) . . ?
O2 C10 C11 127.1(3) . . ?
C11 C10 C9 107.4(2) . . ?
C2 C9 H9 107.6 . . ?
C10 C9 C2 113.7(2) . . ?
C10 C9 H9 107.6 . . ?
C13 C9 C2 116.3(2) . . ?
C13 C9 C10 103.6(2) . . ?
C13 C9 H9 107.6 . . ?
O3 C13 C9 126.3(2) . . ?
O3 C13 C12 125.8(3) . . ?
C12 C13 C9 107.8(2) . . ?
C21 C20 C19 110.6(2) . . ?
C23 C20 C21 121.0(3) . . ?
C23 C20 C19 128.4(3) . . ?
O4 C19 C18 126.1(2) . . ?
O4 C19 C20 126.2(3) . . ?
C20 C19 C18 107.6(2) . . ?
C12 C11 C10 110.0(2) . . ?
C12 C11 C14 121.2(3) . . ?
C14 C11 C10 128.8(3) . . ?
C20 C23 H23 121.4 . . ?
C20 C23 C24 117.2(3) . . ?
C24 C23 H23 121.4 . . ?
C21 C26 H26 121.7 . . ?
C21 C26 C25 116.6(3) . . ?
C25 C26 H26 121.7 . . ?
C23 C24 H24 119.3 . . ?
C25 C24 C23 121.5(3) . . ?
C25 C24 H24 119.3 . . ?
C11 C12 C13 110.6(2) . . ?
C11 C12 C17 121.5(3) . . ?
C17 C12 C13 127.9(3) . . ?
C26 C25 H25 119.1 . . ?
C24 C25 C26 121.9(3) . . ?
C24 C25 H25 119.1 . . ?
C11 C14 H14 121.3 . . ?
C15 C14 C11 117.3(4) . . ?
C15 C14 H14 121.3 . . ?
C14 C15 H15 119.1 . . ?
C14 C15 C16 121.8(3) . . ?
C16 C15 H15 119.1 . . ?
C12 C17 H17 121.4 . . ?
C16 C17 C12 117.2(3) . . ?
C16 C17 H17 121.4 . . ?
C15 C16 H16 119.5 . . ?
C17 C16 C15 121.0(3) . . ?
C17 C16 H16 119.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C3 -177.5(3) . . . . ?
O1 C1 C2 C18 63.4(3) . . . . ?
O1 C1 C2 C9 -57.9(3) . . . . ?
N1 C1 C2 C3 6.3(3) . . . . ?
N1 C1 C2 C18 -112.8(2) . . . . ?
N1 C1 C2 C9 125.9(2) . . . . ?
N1 C8 C3 C4 -177.7(2) . . . . ?
N1 C8 C3 C2 1.2(3) . . . . ?
N1 C8 C7 C6 176.6(3) . . . . ?
O3 C13 C12 C11 176.3(3) . . . . ?
O3 C13 C12 C17 -1.6(6) . . . . ?
O5 C22 C18 C2 -51.5(4) . . . . ?
O5 C22 C18 C19 -178.0(3) . . . . ?
O5 C22 C21 C20 179.9(3) . . . . ?
O5 C22 C21 C26 0.4(5) . . . . ?
O2 C10 C9 C2 45.1(4) . . . . ?
O2 C10 C9 C13 172.2(3) . . . . ?
O2 C10 C11 C12 -174.8(3) . . . . ?
O2 C10 C11 C14 3.2(6) . . . . ?
C1 N1 C8 C3 3.2(3) . . . . ?
C1 N1 C8 C7 -176.5(3) . . . . ?
C1 C2 C9 C10 -65.4(3) . . . . ?
C1 C2 C9 C13 174.4(2) . . . . ?
C8 N1 C1 O1 177.8(3) . . . . ?
C8 N1 C1 C2 -6.1(3) . . . . ?
C8 C3 C4 C5 -0.1(4) . . . . ?
C8 C3 C2 C1 -4.4(3) . . . . ?
C8 C3 C2 C18 110.5(2) . . . . ?
C8 C3 C2 C9 -122.3(2) . . . . ?
C3 C8 C7 C6 -3.1(4) . . . . ?
C3 C2 C9 C10 47.4(3) . . . . ?
C3 C2 C9 C13 -72.8(3) . . . . ?
C5 C6 C7 C8 2.4(4) . . . . ?
C6 C5 C4 C3 -0.6(4) . . . . ?
C4 C3 C2 C1 174.3(3) . . . . ?
C4 C3 C2 C18 -70.7(4) . . . . ?
C4 C3 C2 C9 56.5(4) . . . . ?
C4 C5 C6 C7 -0.6(5) . . . . ?
C22 C18 C2 C1 -57.7(3) . . . . ?
C22 C18 C2 C3 -169.1(2) . . . . ?
C22 C18 C2 C9 62.9(3) . . . . ?
C22 C18 C19 O4 178.2(3) . . . . ?
C22 C18 C19 C20 -3.2(3) . . . . ?
C22 C21 C20 C19 -1.8(3) . . . . ?
C22 C21 C20 C23 178.8(3) . . . . ?
C22 C21 C26 C25 -179.6(3) . . . . ?
C7 C8 C3 C4 2.1(4) . . . . ?
C7 C8 C3 C2 -179.0(2) . . . . ?
C18 C22 C21 C20 -0.4(3) . . . . ?
C18 C22 C21 C26 -179.9(3) . . . . ?
C18 C2 C9 C10 175.7(2) . . . . ?
C18 C2 C9 C13 55.5(3) . . . . ?
C21 C22 C18 C2 128.7(2) . . . . ?
C21 C22 C18 C19 2.2(3) . . . . ?
C21 C20 C19 O4 -178.2(3) . . . . ?
C21 C20 C19 C18 3.3(3) . . . . ?
C21 C20 C23 C24 0.6(4) . . . . ?
C21 C26 C25 C24 0.9(5) . . . . ?
C2 C3 C4 C5 -178.8(3) . . . . ?
C2 C18 C19 O4 52.9(4) . . . . ?
C2 C18 C19 C20 -128.5(2) . . . . ?
C2 C9 C13 O3 -48.4(4) . . . . ?
C2 C9 C13 C12 133.0(3) . . . . ?
C10 C9 C13 O3 -173.8(3) . . . . ?
C10 C9 C13 C12 7.5(3) . . . . ?
C10 C11 C12 C13 0.0(4) . . . . ?
C10 C11 C12 C17 178.1(3) . . . . ?
C10 C11 C14 C15 -177.9(4) . . . . ?
C9 C10 C11 C12 4.9(4) . . . . ?
C9 C10 C11 C14 -177.1(4) . . . . ?
C9 C13 C12 C11 -5.0(4) . . . . ?
C9 C13 C12 C17 177.1(4) . . . . ?
C13 C12 C17 C16 178.4(4) . . . . ?
C20 C21 C26 C25 0.9(4) . . . . ?
C20 C23 C24 C25 1.2(5) . . . . ?
C19 C18 C2 C1 62.2(3) . . . . ?
C19 C18 C2 C3 -49.3(3) . . . . ?
C19 C18 C2 C9 -177.3(2) . . . . ?
C19 C20 C23 C24 -178.7(3) . . . . ?
C11 C10 C9 C2 -134.6(2) . . . . ?
C11 C10 C9 C13 -7.5(3) . . . . ?
C11 C12 C17 C16 0.6(6) . . . . ?
C11 C14 C15 C16 -0.3(8) . . . . ?
C23 C20 C19 O4 1.2(5) . . . . ?
C23 C20 C19 C18 -177.4(3) . . . . ?
C23 C24 C25 C26 -2.0(5) . . . . ?
C26 C21 C20 C19 177.7(3) . . . . ?
C26 C21 C20 C23 -1.7(5) . . . . ?
C12 C11 C14 C15 -0.1(6) . . . . ?
C12 C17 C16 C15 -1.1(8) . . . . ?
C14 C11 C12 C13 -178.2(3) . . . . ?
C14 C11 C12 C17 -0.1(6) . . . . ?
C14 C15 C16 C17 0.9(9) . . . . ?

_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.203
_oxdiff_exptl_absorpt_empirical_full_min 0.799
####################################################################### 
# 
# 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_cu_dwg24jc02
_database_code_depnum_ccdc_archive 'CCDC 2390188'
loop_
_audit_author_name
_audit_author_address
'Jack Clegg'
;The University of Queensalnd
Australia
;
_audit_update_record             
;
2024-11-07 deposited with the CCDC.	2024-11-27 downloaded from the CCDC.
;
_audit_creation_date             2024-10-11
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.01.12 svn.r2f8d729c for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2019/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C28 H18 N2 O3, 0.5[CH2Cl2]'
_chemical_formula_sum            'C28.50 H19 Cl N2 O3'
_chemical_formula_weight         472.91
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 '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/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   12.3461(7)
_cell_length_b                   9.1978(5)
_cell_length_c                   20.5495(11)
_cell_angle_alpha                90
_cell_angle_beta                 102.858(4)
_cell_angle_gamma                90
_cell_volume                     2275.0(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9953
_cell_measurement_temperature    150.00
_cell_measurement_theta_max      60.541
_cell_measurement_theta_min      3.841
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.771
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.6403
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1783 before and 0.1097 after correction.
The Ratio of minimum to maximum transmission is 0.8502.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.381
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             980
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.01
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1493
_diffrn_reflns_av_unetI/netI     0.0564
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            104411
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.790
_diffrn_reflns_theta_min         3.840
_diffrn_ambient_temperature      150.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  BrukerD8
_diffrn_measurement_method       ?
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2720
_reflns_number_total             4170
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _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       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.698
_refine_diff_density_min         -0.304
_refine_diff_density_rms         0.093
_refine_ls_extinction_coef       0.0094(8)
_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   1.076
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     300
_refine_ls_number_reflns         4170
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0962
_refine_ls_R_factor_gt           0.0649
_refine_ls_restrained_S_all      1.076
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1157P)²+0.1729P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1823
_refine_ls_wR_factor_ref         0.1982
_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) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C6(H6a,H6b)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C1(H1a), C2(H2), C9(H9), C10(H10), C11(H11), C12(H12), C13(H13),
 C18(H18), C22(H22), C23(H23), C24(H24), C25(H25)
2.c Idealised Me refined as rotating group:
 C28(H28a,H28b,H28c)
;
_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 0.5509(2) 0.7119(3) 0.42386(11) 0.0715(8) Uani 1 1 d . . . . .
O2 O 0.4268(2) 0.5019(2) 0.11123(10) 0.0558(6) Uani 1 1 d . . . . .
O3 O 0.6847(2) 0.5554(2) 0.13157(10) 0.0551(6) Uani 1 1 d . . . . .
N1 N 0.7136(2) 0.3274(3) 0.32469(11) 0.0449(6) Uani 1 1 d . . . . .
H1 H 0.736342 0.239128 0.337430 0.054 Uiso 1 1 calc R U . . .
N2 N 0.6406(2) 0.3198(3) 0.09941(11) 0.0452(6) Uani 1 1 d . . . . .
C1 C 0.5182(3) -0.0349(4) 0.13149(18) 0.0560(9) Uani 1 1 d . . . . .
H1A H 0.498536 -0.128086 0.112640 0.067 Uiso 1 1 calc R U . . .
C2 C 0.5671(3) 0.0650(4) 0.09626(16) 0.0512(8) Uani 1 1 d . . . . .
H2 H 0.582125 0.041634 0.054111 0.061 Uiso 1 1 calc R U . . .
C3 C 0.5928(3) 0.1998(3) 0.12521(14) 0.0447(7) Uani 1 1 d . . . . .
C4 C 0.5740(2) 0.2335(3) 0.18802(14) 0.0413(7) Uani 1 1 d . . . . .
C5 C 0.6175(2) 0.3840(3) 0.20650(13) 0.0410(7) Uani 1 1 d . . . . .
C6 C 0.7266(3) 0.3795(4) 0.25961(13) 0.0442(7) Uani 1 1 d . . . . .
H6A H 0.779702 0.315345 0.243695 0.053 Uiso 1 1 calc R U . . .
H6B H 0.758943 0.478392 0.264970 0.053 Uiso 1 1 calc R U . . .
C7 C 0.6687(2) 0.4086(3) 0.36530(13) 0.0404(7) Uani 1 1 d . . . . .
C8 C 0.7016(3) 0.3880(3) 0.43884(13) 0.0435(7) Uani 1 1 d . . . . .
C9 C 0.7721(3) 0.2896(3) 0.47817(14) 0.0487(8) Uani 1 1 d . . . . .
H9 H 0.805806 0.212719 0.458909 0.058 Uiso 1 1 calc R U . . .
C10 C 0.7917(3) 0.3077(4) 0.54722(14) 0.0518(8) Uani 1 1 d . . . . .
H10 H 0.839265 0.241517 0.575533 0.062 Uiso 1 1 calc R U . . .
C11 C 0.7434(3) 0.4197(4) 0.57521(15) 0.0539(9) Uani 1 1 d . . . . .
H11 H 0.758240 0.428832 0.622414 0.065 Uiso 1 1 calc R U . . .
C12 C 0.4975(3) -0.0027(3) 0.19275(17) 0.0505(8) Uani 1 1 d . . . . .
H12 H 0.464145 -0.073615 0.215673 0.061 Uiso 1 1 calc R U . . .
C13 C 0.5248(3) 0.1323(3) 0.22138(15) 0.0471(8) Uani 1 1 d . . . . .
H13 H 0.509751 0.154877 0.263610 0.057 Uiso 1 1 calc R U . . .
C14 C 0.5351(3) 0.4902(3) 0.22417(14) 0.0434(7) Uani 1 1 d . . . . .
C15 C 0.5272(2) 0.5546(3) 0.28312(14) 0.0406(7) Uani 1 1 d . . . . .
C16 C 0.5944(3) 0.5251(3) 0.34931(14) 0.0430(7) Uani 1 1 d . . . . .
C17 C 0.6537(3) 0.5000(3) 0.46717(15) 0.0460(8) Uani 1 1 d . . . . .
C18 C 0.6736(3) 0.5191(4) 0.53604(15) 0.0533(9) Uani 1 1 d . . . . .
H18 H 0.640818 0.596760 0.555282 0.064 Uiso 1 1 calc R U . . .
C19 C 0.5901(3) 0.5942(4) 0.41317(15) 0.0502(8) Uani 1 1 d . . . . .
C20 C 0.4258(3) 0.6526(3) 0.26838(14) 0.0437(7) Uani 1 1 d . . . . .
C21 C 0.3765(3) 0.6407(3) 0.19998(14) 0.0440(7) Uani 1 1 d . . . . .
C22 C 0.2802(3) 0.7124(3) 0.17071(16) 0.0526(8) Uani 1 1 d . . . . .
H22 H 0.248759 0.701730 0.124374 0.063 Uiso 1 1 calc R U . . .
C23 C 0.2298(3) 0.8012(4) 0.21038(17) 0.0562(9) Uani 1 1 d . . . . .
H23 H 0.163655 0.852803 0.191393 0.067 Uiso 1 1 calc R U . . .
C24 C 0.2768(3) 0.8127(4) 0.27695(17) 0.0581(9) Uani 1 1 d . . . . .
H24 H 0.241454 0.872052 0.303890 0.070 Uiso 1 1 calc R U . . .
C25 C 0.3746(3) 0.7409(3) 0.30690(16) 0.0520(8) Uani 1 1 d . . . . .
H25 H 0.405656 0.752450 0.353241 0.062 Uiso 1 1 calc R U . . .
C26 C 0.4434(3) 0.5400(3) 0.17007(14) 0.0443(8) Uani 1 1 d . . . . .
C27 C 0.6494(3) 0.4331(3) 0.14198(14) 0.0437(7) Uani 1 1 d . . . . .
C28 C 0.6559(3) 0.3310(4) 0.03098(14) 0.0597(9) Uani 1 1 d . . . . .
H28A H 0.583274 0.339511 0.000061 0.090 Uiso 1 1 calc R U . . .
H28B H 0.693944 0.243793 0.020081 0.090 Uiso 1 1 calc R U . . .
H28C H 0.700751 0.417038 0.026988 0.090 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 C19 1.225(4) . ?
O2 C26 1.231(3) . ?
O3 C27 1.242(3) . ?
N1 H1 0.8800 . ?
N1 C6 1.462(3) . ?
N1 C7 1.329(4) . ?
N2 C3 1.409(4) . ?
N2 C27 1.349(4) . ?
N2 C28 1.464(3) . ?
C1 H1A 0.9500 . ?
C1 C2 1.388(5) . ?
C1 C12 1.372(5) . ?
C2 H2 0.9500 . ?
C2 C3 1.382(4) . ?
C3 C4 1.396(4) . ?
C4 C5 1.503(4) . ?
C4 C13 1.375(4) . ?
C5 C6 1.534(4) . ?
C5 C14 1.511(4) . ?
C5 C27 1.533(4) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.487(4) . ?
C7 C16 1.401(4) . ?
C8 C9 1.385(4) . ?
C8 C17 1.379(4) . ?
C9 H9 0.9500 . ?
C9 C10 1.395(4) . ?
C10 H10 0.9500 . ?
C10 C11 1.378(5) . ?
C11 H11 0.9500 . ?
C11 C18 1.384(5) . ?
C12 H12 0.9500 . ?
C12 C13 1.384(4) . ?
C13 H13 0.9500 . ?
C14 C15 1.371(4) . ?
C14 C26 1.472(4) . ?
C15 C16 1.452(4) . ?
C15 C20 1.518(4) . ?
C16 C19 1.470(4) . ?
C17 C18 1.393(4) . ?
C17 C19 1.487(4) . ?
C18 H18 0.9500 . ?
C20 C21 1.406(4) . ?
C20 C25 1.381(4) . ?
C21 C22 1.375(4) . ?
C21 C26 1.465(4) . ?
C22 H22 0.9500 . ?
C22 C23 1.395(5) . ?
C23 H23 0.9500 . ?
C23 C24 1.366(5) . ?
C24 H24 0.9500 . ?
C24 C25 1.394(4) . ?
C25 H25 0.9500 . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 N1 H1 118.8 . . ?
C7 N1 H1 118.8 . . ?
C7 N1 C6 122.4(2) . . ?
C3 N2 C28 124.8(2) . . ?
C27 N2 C3 110.0(2) . . ?
C27 N2 C28 124.0(3) . . ?
C2 C1 H1A 119.1 . . ?
C12 C1 H1A 119.1 . . ?
C12 C1 C2 121.9(3) . . ?
C1 C2 H2 121.5 . . ?
C3 C2 C1 117.0(3) . . ?
C3 C2 H2 121.5 . . ?
C2 C3 N2 128.1(3) . . ?
C2 C3 C4 121.8(3) . . ?
C4 C3 N2 110.1(3) . . ?
C3 C4 C5 108.3(3) . . ?
C13 C4 C3 119.6(3) . . ?
C13 C4 C5 132.1(3) . . ?
C4 C5 C6 111.2(2) . . ?
C4 C5 C14 115.7(2) . . ?
C4 C5 C27 101.5(2) . . ?
C14 C5 C6 112.2(2) . . ?
C14 C5 C27 109.5(2) . . ?
C27 C5 C6 105.6(2) . . ?
N1 C6 C5 113.7(2) . . ?
N1 C6 H6A 108.8 . . ?
N1 C6 H6B 108.8 . . ?
C5 C6 H6A 108.8 . . ?
C5 C6 H6B 108.8 . . ?
H6A C6 H6B 107.7 . . ?
N1 C7 C8 120.6(3) . . ?
N1 C7 C16 128.7(3) . . ?
C16 C7 C8 110.6(3) . . ?
C9 C8 C7 132.1(3) . . ?
C17 C8 C7 106.7(3) . . ?
C17 C8 C9 121.0(3) . . ?
C8 C9 H9 121.3 . . ?
C8 C9 C10 117.3(3) . . ?
C10 C9 H9 121.3 . . ?
C9 C10 H10 119.3 . . ?
C11 C10 C9 121.4(3) . . ?
C11 C10 H10 119.3 . . ?
C10 C11 H11 119.3 . . ?
C10 C11 C18 121.4(3) . . ?
C18 C11 H11 119.3 . . ?
C1 C12 H12 119.8 . . ?
C1 C12 C13 120.4(3) . . ?
C13 C12 H12 119.8 . . ?
C4 C13 C12 119.3(3) . . ?
C4 C13 H13 120.4 . . ?
C12 C13 H13 120.4 . . ?
C15 C14 C5 132.5(3) . . ?
C15 C14 C26 109.8(3) . . ?
C26 C14 C5 117.7(3) . . ?
C14 C15 C16 127.5(3) . . ?
C14 C15 C20 107.3(3) . . ?
C16 C15 C20 124.9(3) . . ?
C7 C16 C15 124.8(3) . . ?
C7 C16 C19 105.9(2) . . ?
C15 C16 C19 128.9(3) . . ?
C8 C17 C18 121.8(3) . . ?
C8 C17 C19 109.0(3) . . ?
C18 C17 C19 129.0(3) . . ?
C11 C18 C17 117.0(3) . . ?
C11 C18 H18 121.5 . . ?
C17 C18 H18 121.5 . . ?
O1 C19 C16 129.5(3) . . ?
O1 C19 C17 123.0(3) . . ?
C16 C19 C17 107.2(3) . . ?
C21 C20 C15 107.9(3) . . ?
C25 C20 C15 134.2(3) . . ?
C25 C20 C21 117.8(3) . . ?
C20 C21 C26 108.0(3) . . ?
C22 C21 C20 122.7(3) . . ?
C22 C21 C26 129.3(3) . . ?
C21 C22 H22 120.7 . . ?
C21 C22 C23 118.7(3) . . ?
C23 C22 H22 120.7 . . ?
C22 C23 H23 120.5 . . ?
C24 C23 C22 119.0(3) . . ?
C24 C23 H23 120.5 . . ?
C23 C24 H24 118.7 . . ?
C23 C24 C25 122.6(3) . . ?
C25 C24 H24 118.7 . . ?
C20 C25 C24 119.2(3) . . ?
C20 C25 H25 120.4 . . ?
C24 C25 H25 120.4 . . ?
O2 C26 C14 125.8(3) . . ?
O2 C26 C21 127.3(3) . . ?
C21 C26 C14 106.9(2) . . ?
O3 C27 N2 124.7(3) . . ?
O3 C27 C5 125.7(3) . . ?
N2 C27 C5 109.5(3) . . ?
N2 C28 H28A 109.5 . . ?
N2 C28 H28B 109.5 . . ?
N2 C28 H28C 109.5 . . ?
H28A C28 H28B 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C7 C8 C9 -3.4(5) . . . . ?
N1 C7 C8 C17 171.6(3) . . . . ?
N1 C7 C16 C15 18.5(5) . . . . ?
N1 C7 C16 C19 -168.4(3) . . . . ?
N2 C3 C4 C5 -2.9(3) . . . . ?
N2 C3 C4 C13 178.2(3) . . . . ?
C1 C2 C3 N2 -178.8(3) . . . . ?
C1 C2 C3 C4 1.9(4) . . . . ?
C1 C12 C13 C4 -0.6(5) . . . . ?
C2 C1 C12 C13 0.2(5) . . . . ?
C2 C3 C4 C5 176.5(3) . . . . ?
C2 C3 C4 C13 -2.4(4) . . . . ?
C3 N2 C27 O3 -177.2(3) . . . . ?
C3 N2 C27 C5 6.8(3) . . . . ?
C3 C4 C5 C6 -105.6(3) . . . . ?
C3 C4 C5 C14 124.8(3) . . . . ?
C3 C4 C5 C27 6.4(3) . . . . ?
C3 C4 C13 C12 1.7(4) . . . . ?
C4 C5 C6 N1 -67.8(3) . . . . ?
C4 C5 C14 C15 110.9(4) . . . . ?
C4 C5 C14 C26 -69.6(3) . . . . ?
C4 C5 C27 O3 176.1(3) . . . . ?
C4 C5 C27 N2 -8.1(3) . . . . ?
C5 C4 C13 C12 -176.9(3) . . . . ?
C5 C14 C15 C16 -6.8(5) . . . . ?
C5 C14 C15 C20 179.4(3) . . . . ?
C5 C14 C26 O2 0.7(5) . . . . ?
C5 C14 C26 C21 -180.0(2) . . . . ?
C6 N1 C7 C8 -151.3(3) . . . . ?
C6 N1 C7 C16 24.3(5) . . . . ?
C6 C5 C14 C15 -18.3(4) . . . . ?
C6 C5 C14 C26 161.2(3) . . . . ?
C6 C5 C27 O3 -67.8(4) . . . . ?
C6 C5 C27 N2 108.1(3) . . . . ?
C7 N1 C6 C5 -74.5(3) . . . . ?
C7 C8 C9 C10 175.0(3) . . . . ?
C7 C8 C17 C18 -175.8(3) . . . . ?
C7 C8 C17 C19 -0.2(3) . . . . ?
C7 C16 C19 O1 167.3(4) . . . . ?
C7 C16 C19 C17 -7.4(4) . . . . ?
C8 C7 C16 C15 -165.6(3) . . . . ?
C8 C7 C16 C19 7.5(3) . . . . ?
C8 C9 C10 C11 -0.4(5) . . . . ?
C8 C17 C18 C11 -0.4(5) . . . . ?
C8 C17 C19 O1 -170.4(3) . . . . ?
C8 C17 C19 C16 4.7(4) . . . . ?
C9 C8 C17 C18 -0.1(5) . . . . ?
C9 C8 C17 C19 175.5(3) . . . . ?
C9 C10 C11 C18 -0.2(5) . . . . ?
C10 C11 C18 C17 0.6(5) . . . . ?
C12 C1 C2 C3 -0.9(5) . . . . ?
C13 C4 C5 C6 73.1(4) . . . . ?
C13 C4 C5 C14 -56.5(4) . . . . ?
C13 C4 C5 C27 -174.9(3) . . . . ?
C14 C5 C6 N1 63.6(3) . . . . ?
C14 C5 C27 O3 53.3(4) . . . . ?
C14 C5 C27 N2 -130.9(3) . . . . ?
C14 C15 C16 C7 -10.2(5) . . . . ?
C14 C15 C16 C19 178.4(3) . . . . ?
C14 C15 C20 C21 0.5(3) . . . . ?
C14 C15 C20 C25 178.1(3) . . . . ?
C15 C14 C26 O2 -179.7(3) . . . . ?
C15 C14 C26 C21 -0.4(3) . . . . ?
C15 C16 C19 O1 -20.0(6) . . . . ?
C15 C16 C19 C17 165.2(3) . . . . ?
C15 C20 C21 C22 177.8(3) . . . . ?
C15 C20 C21 C26 -0.7(3) . . . . ?
C15 C20 C25 C24 -176.9(3) . . . . ?
C16 C7 C8 C9 -179.7(3) . . . . ?
C16 C7 C8 C17 -4.7(3) . . . . ?
C16 C15 C20 C21 -173.5(3) . . . . ?
C16 C15 C20 C25 4.1(5) . . . . ?
C17 C8 C9 C10 0.5(5) . . . . ?
C18 C17 C19 O1 4.8(6) . . . . ?
C18 C17 C19 C16 180.0(3) . . . . ?
C19 C17 C18 C11 -175.1(3) . . . . ?
C20 C15 C16 C7 162.5(3) . . . . ?
C20 C15 C16 C19 -8.9(5) . . . . ?
C20 C21 C22 C23 0.3(5) . . . . ?
C20 C21 C26 O2 -180.0(3) . . . . ?
C20 C21 C26 C14 0.7(3) . . . . ?
C21 C20 C25 C24 0.5(5) . . . . ?
C21 C22 C23 C24 -0.7(5) . . . . ?
C22 C21 C26 O2 1.7(5) . . . . ?
C22 C21 C26 C14 -177.7(3) . . . . ?
C22 C23 C24 C25 1.0(5) . . . . ?
C23 C24 C25 C20 -0.9(5) . . . . ?
C25 C20 C21 C22 -0.2(5) . . . . ?
C25 C20 C21 C26 -178.8(3) . . . . ?
C26 C14 C15 C16 173.7(3) . . . . ?
C26 C14 C15 C20 -0.1(3) . . . . ?
C26 C21 C22 C23 178.5(3) . . . . ?
C27 N2 C3 C2 178.1(3) . . . . ?
C27 N2 C3 C4 -2.5(3) . . . . ?
C27 C5 C6 N1 -177.1(2) . . . . ?
C27 C5 C14 C15 -135.2(3) . . . . ?
C27 C5 C14 C26 44.2(3) . . . . ?
C28 N2 C3 C2 10.3(5) . . . . ?
C28 N2 C3 C4 -170.3(3) . . . . ?
C28 N2 C27 O3 -9.3(5) . . . . ?
C28 N2 C27 C5 174.7(3) . . . . ?

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 0.000 0.500 0.000 160.9 62.3 '1 CH2Cl2'
2 0.500 0.000 0.500 160.9 62.3 '1 CH2Cl2'

_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_gwg23jc02_auto
_database_code_depnum_ccdc_archive 'CCDC 2390184'
loop_
_audit_author_name
_audit_author_address
'Jack Clegg'
;The University of Queensalnd
Australia
;
_audit_update_record             
;
2024-10-11 deposited with the CCDC.	2024-11-27 downloaded from the CCDC.
;
_audit_creation_date             2024-10-11
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.01.12 svn.r2f8d729c for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H13 N O3'
_chemical_formula_sum            'C19 H13 N O3'
_chemical_formula_weight         303.30
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C26 H15 N O5'
_chemical_oxdiff_usercomment     'oidb - clear crystal'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   6.9394(6)
_cell_length_b                   10.6577(8)
_cell_length_c                   10.8516(9)
_cell_angle_alpha                64.849(8)
_cell_angle_beta                 81.266(7)
_cell_angle_gamma                87.520(7)
_cell_volume                     717.84(11)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1984
_cell_measurement_temperature    190(2)
_cell_measurement_theta_max      29.7670
_cell_measurement_theta_min      3.0330
_shelx_estimated_absorpt_T_max   0.995
_shelx_estimated_absorpt_T_min   0.972
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.81011
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.123a (Rigaku Oxford Diffraction, 2022)
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    1.403
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             316
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0315
_diffrn_reflns_av_unetI/netI     0.0491
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            5628
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.123
_diffrn_reflns_theta_max         25.123
_diffrn_reflns_theta_min         2.971
_diffrn_ambient_temperature      190(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0217
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -48.00  36.00   1.00   15.00    --   19.52 -57.00  90.00   84
  2  ω     18.00  74.00   1.00   15.00    --   19.52  38.00 -90.00   56
  3  ω     -7.00  38.00   1.00   15.00    --   19.52  77.00 -30.00   45
  4  ω     -5.00  29.00   1.00   15.00    --   19.52  77.00  90.00   34
  5  ω     -7.00  29.00   1.00   15.00    --   19.52  77.00-150.00   36
  6  ω      4.00  47.00   1.00   15.00    --  -20.77  57.00 120.00   43
  7  ω    -88.00 -23.00   1.00   15.00    --  -20.77 -57.00-150.00   65
  8  ω    -33.00  47.00   1.00   15.00    --  -20.77  57.00   0.00   80
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, EosS2, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0378836000
_diffrn_orient_matrix_UB_12      0.0647339000
_diffrn_orient_matrix_UB_13      -0.0094249000
_diffrn_orient_matrix_UB_21      -0.0656014000
_diffrn_orient_matrix_UB_22      -0.0027350000
_diffrn_orient_matrix_UB_23      0.0580290000
_diffrn_orient_matrix_UB_31      0.0704388000
_diffrn_orient_matrix_UB_32      -0.0347962000
_diffrn_orient_matrix_UB_33      0.0432911000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2009
_reflns_number_total             2571
_reflns_odcompleteness_completeness 99.89
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     28.22
_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 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.167
_refine_diff_density_min         -0.180
_refine_diff_density_rms         0.040
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         2571
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0611
_refine_ls_R_factor_gt           0.0437
_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)+(0.0411P)²+0.0364P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0926
_refine_ls_wR_factor_ref         0.1026
_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:
 C18(H18A,H18B)
2.b Aromatic/amide H refined with riding coordinates:
 C13(H13), C6(H6), C16(H16), C9(H9), C15(H15), C14(H14), C7(H7), C8(H8)
2.c Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C)
;
_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 0.77876(17) 0.33610(14) 0.95291(11) 0.0357(3) Uani 1 1 d . . . . .
O2 O 0.45896(17) 0.35145(14) 0.93915(12) 0.0384(4) Uani 1 1 d . . . . .
O3 O 0.66556(19) 0.66268(13) 0.70432(12) 0.0410(4) Uani 1 1 d . . . . .
N1 N 0.7742(2) 0.36247(14) 0.47833(13) 0.0269(4) Uani 1 1 d . . . . .
C2 C 0.7083(2) 0.47443(17) 0.63357(16) 0.0239(4) Uani 1 1 d . . . . .
C1 C 0.7544(2) 0.47305(17) 0.50170(16) 0.0238(4) Uani 1 1 d . . . . .
C17 C 0.6245(2) 0.34772(17) 0.88999(16) 0.0256(4) Uani 1 1 d . . . . .
C11 C 0.7405(2) 0.70626(18) 0.46299(16) 0.0264(4) Uani 1 1 d . . . . .
C5 C 0.7460(2) 0.23725(17) 0.59399(16) 0.0253(4) Uani 1 1 d . . . . .
C4 C 0.7009(2) 0.22699(17) 0.73033(16) 0.0245(4) Uani 1 1 d . . . . .
C12 C 0.7760(2) 0.61819(17) 0.39667(16) 0.0240(4) Uani 1 1 d . . . . .
C13 C 0.8242(2) 0.67110(19) 0.25565(17) 0.0294(4) Uani 1 1 d . . . . .
H13 H 0.849534 0.611589 0.210438 0.035 Uiso 1 1 calc R U . . .
C3 C 0.6820(2) 0.35232(18) 0.74857(16) 0.0240(4) Uani 1 1 d . . . . .
C6 C 0.6754(2) 0.09414(18) 0.84088(17) 0.0292(4) Uani 1 1 d . . . . .
H6 H 0.646372 0.085737 0.932517 0.035 Uiso 1 1 calc R U . . .
C16 C 0.7496(3) 0.84879(19) 0.38833(19) 0.0334(5) Uani 1 1 d . . . . .
H16 H 0.723791 0.908667 0.433098 0.040 Uiso 1 1 calc R U . . .
C10 C 0.6983(2) 0.62171(18) 0.61407(18) 0.0285(4) Uani 1 1 d . . . . .
C9 C 0.7631(3) 0.11532(18) 0.57419(18) 0.0325(4) Uani 1 1 d . . . . .
H9 H 0.794720 0.121256 0.483541 0.039 Uiso 1 1 calc R U . . .
C15 C 0.7972(3) 0.90171(19) 0.24673(19) 0.0372(5) Uani 1 1 d . . . . .
H15 H 0.804464 0.999262 0.193455 0.045 Uiso 1 1 calc R U . . .
C14 C 0.8344(3) 0.8143(2) 0.18179(19) 0.0361(5) Uani 1 1 d . . . . .
H14 H 0.867610 0.853120 0.084476 0.043 Uiso 1 1 calc R U . . .
C7 C 0.6918(3) -0.02218(19) 0.81805(18) 0.0327(4) Uani 1 1 d . . . . .
H7 H 0.673748 -0.110811 0.893790 0.039 Uiso 1 1 calc R U . . .
C18 C 0.7374(3) 0.3367(2) 1.08962(18) 0.0400(5) Uani 1 1 d . . . . .
H18A H 0.640658 0.262554 1.150687 0.048 Uiso 1 1 calc R U . . .
H18B H 0.683824 0.426951 1.081951 0.048 Uiso 1 1 calc R U . . .
C8 C 0.7350(3) -0.01240(19) 0.68372(19) 0.0356(5) Uani 1 1 d . . . . .
H8 H 0.744774 -0.094103 0.668607 0.043 Uiso 1 1 calc R U . . .
C19 C 0.9257(3) 0.3127(2) 1.14695(19) 0.0467(6) Uani 1 1 d . . . . .
H19A H 1.023129 0.382747 1.082311 0.070 Uiso 1 1 calc R U . . .
H19B H 0.971982 0.220158 1.160849 0.070 Uiso 1 1 calc R U . . .
H19C H 0.905254 0.319652 1.235201 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 C17 1.329(2) . ?
O1 C18 1.470(2) . ?
O2 C17 1.1971(19) . ?
O3 C10 1.220(2) . ?
N1 C1 1.304(2) . ?
N1 C5 1.385(2) . ?
C2 C1 1.424(2) . ?
C2 C3 1.362(2) . ?
C2 C10 1.492(2) . ?
C1 C12 1.478(2) . ?
C17 C3 1.506(2) . ?
C11 C12 1.400(2) . ?
C11 C16 1.384(2) . ?
C11 C10 1.486(2) . ?
C5 C4 1.423(2) . ?
C5 C9 1.402(2) . ?
C4 C3 1.429(2) . ?
C4 C6 1.410(2) . ?
C12 C13 1.378(2) . ?
C13 H13 0.9500 . ?
C13 C14 1.389(3) . ?
C6 H6 0.9500 . ?
C6 C7 1.361(3) . ?
C16 H16 0.9500 . ?
C16 C15 1.383(3) . ?
C9 H9 0.9500 . ?
C9 C8 1.372(2) . ?
C15 H15 0.9500 . ?
C15 C14 1.383(3) . ?
C14 H14 0.9500 . ?
C7 H7 0.9500 . ?
C7 C8 1.402(3) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C18 C19 1.498(2) . ?
C8 H8 0.9500 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 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
C17 O1 C18 115.51(13) . . ?
C1 N1 C5 115.52(14) . . ?
C1 C2 C10 108.36(14) . . ?
C3 C2 C1 119.62(16) . . ?
C3 C2 C10 132.02(15) . . ?
N1 C1 C2 125.69(15) . . ?
N1 C1 C12 126.15(15) . . ?
C2 C1 C12 108.16(14) . . ?
O1 C17 C3 111.68(14) . . ?
O2 C17 O1 124.94(15) . . ?
O2 C17 C3 123.36(15) . . ?
C12 C11 C10 109.35(15) . . ?
C16 C11 C12 120.82(16) . . ?
C16 C11 C10 129.84(17) . . ?
N1 C5 C4 123.30(15) . . ?
N1 C5 C9 117.72(15) . . ?
C9 C5 C4 118.98(15) . . ?
C5 C4 C3 118.25(14) . . ?
C6 C4 C5 118.66(16) . . ?
C6 C4 C3 123.09(15) . . ?
C11 C12 C1 108.65(14) . . ?
C13 C12 C1 130.43(16) . . ?
C13 C12 C11 120.91(16) . . ?
C12 C13 H13 121.1 . . ?
C12 C13 C14 117.80(18) . . ?
C14 C13 H13 121.1 . . ?
C2 C3 C17 121.82(15) . . ?
C2 C3 C4 117.60(14) . . ?
C4 C3 C17 120.50(14) . . ?
C4 C6 H6 119.6 . . ?
C7 C6 C4 120.89(16) . . ?
C7 C6 H6 119.6 . . ?
C11 C16 H16 120.9 . . ?
C15 C16 C11 118.19(18) . . ?
C15 C16 H16 120.9 . . ?
O3 C10 C2 126.71(16) . . ?
O3 C10 C11 127.80(17) . . ?
C11 C10 C2 105.47(15) . . ?
C5 C9 H9 119.5 . . ?
C8 C9 C5 120.99(16) . . ?
C8 C9 H9 119.5 . . ?
C16 C15 H15 119.6 . . ?
C14 C15 C16 120.80(17) . . ?
C14 C15 H15 119.6 . . ?
C13 C14 H14 119.3 . . ?
C15 C14 C13 121.49(17) . . ?
C15 C14 H14 119.3 . . ?
C6 C7 H7 119.7 . . ?
C6 C7 C8 120.59(16) . . ?
C8 C7 H7 119.7 . . ?
O1 C18 H18A 110.2 . . ?
O1 C18 H18B 110.2 . . ?
O1 C18 C19 107.37(15) . . ?
H18A C18 H18B 108.5 . . ?
C19 C18 H18A 110.2 . . ?
C19 C18 H18B 110.2 . . ?
C9 C8 C7 119.88(17) . . ?
C9 C8 H8 120.1 . . ?
C7 C8 H8 120.1 . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C17 C3 C2 -95.89(18) . . . . ?
O1 C17 C3 C4 87.43(19) . . . . ?
O2 C17 C3 C2 85.5(2) . . . . ?
O2 C17 C3 C4 -91.2(2) . . . . ?
N1 C1 C12 C11 179.13(16) . . . . ?
N1 C1 C12 C13 -1.6(3) . . . . ?
N1 C5 C4 C3 0.6(2) . . . . ?
N1 C5 C4 C6 -179.90(14) . . . . ?
N1 C5 C9 C8 -179.25(15) . . . . ?
C2 C1 C12 C11 -0.99(18) . . . . ?
C2 C1 C12 C13 178.33(16) . . . . ?
C1 N1 C5 C4 -0.8(2) . . . . ?
C1 N1 C5 C9 179.16(15) . . . . ?
C1 C2 C3 C17 -177.29(14) . . . . ?
C1 C2 C3 C4 -0.5(2) . . . . ?
C1 C2 C10 O3 -178.63(17) . . . . ?
C1 C2 C10 C11 0.22(18) . . . . ?
C1 C12 C13 C14 -179.85(15) . . . . ?
C17 O1 C18 C19 176.09(15) . . . . ?
C11 C12 C13 C14 -0.6(2) . . . . ?
C11 C16 C15 C14 0.1(3) . . . . ?
C5 N1 C1 C2 0.4(2) . . . . ?
C5 N1 C1 C12 -179.78(14) . . . . ?
C5 C4 C3 C2 0.1(2) . . . . ?
C5 C4 C3 C17 176.92(14) . . . . ?
C5 C4 C6 C7 -0.6(2) . . . . ?
C5 C9 C8 C7 -1.1(3) . . . . ?
C4 C5 C9 C8 0.7(3) . . . . ?
C4 C6 C7 C8 0.2(3) . . . . ?
C12 C11 C16 C15 -0.9(2) . . . . ?
C12 C11 C10 O3 177.99(17) . . . . ?
C12 C11 C10 C2 -0.84(18) . . . . ?
C12 C13 C14 C15 -0.2(3) . . . . ?
C3 C2 C1 N1 0.3(3) . . . . ?
C3 C2 C1 C12 -179.58(14) . . . . ?
C3 C2 C10 O3 1.4(3) . . . . ?
C3 C2 C10 C11 -179.75(16) . . . . ?
C3 C4 C6 C7 178.91(16) . . . . ?
C6 C4 C3 C2 -179.39(15) . . . . ?
C6 C4 C3 C17 -2.6(2) . . . . ?
C6 C7 C8 C9 0.7(3) . . . . ?
C16 C11 C12 C1 -179.47(15) . . . . ?
C16 C11 C12 C13 1.1(2) . . . . ?
C16 C11 C10 O3 -1.3(3) . . . . ?
C16 C11 C10 C2 179.84(16) . . . . ?
C16 C15 C14 C13 0.4(3) . . . . ?
C10 C2 C1 N1 -179.67(15) . . . . ?
C10 C2 C1 C12 0.45(18) . . . . ?
C10 C2 C3 C17 2.7(3) . . . . ?
C10 C2 C3 C4 179.45(16) . . . . ?
C10 C11 C12 C1 1.13(18) . . . . ?
C10 C11 C12 C13 -178.26(14) . . . . ?
C10 C11 C16 C15 178.40(16) . . . . ?
C9 C5 C4 C3 -179.38(15) . . . . ?
C9 C5 C4 C6 0.1(2) . . . . ?
C18 O1 C17 O2 -3.9(3) . . . . ?
C18 O1 C17 C3 177.53(14) . . . . ?

_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.237
_oxdiff_exptl_absorpt_empirical_full_min 0.814
####################################################################### 
# 
# 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_cu_dwg24jc04
_database_code_depnum_ccdc_archive 'CCDC 2390189'
loop_
_audit_author_name
_audit_author_address
'Jack Clegg'
;The University of Queensalnd
Australia
;
_audit_update_record             
;
2024-10-11 deposited with the CCDC.	2024-11-27 downloaded from the CCDC.
;
_audit_creation_date             2024-10-11
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.01.12 svn.r2f8d729c for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C27 H15 Br N2 O3, 1[H2O]'
_chemical_formula_sum            'C27 H17 Br N2 O4'
_chemical_formula_weight         513.33
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 '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                   10.5296(5)
_cell_length_b                   20.1852(13)
_cell_length_c                   12.1204(8)
_cell_angle_alpha                90
_cell_angle_beta                 113.100(3)
_cell_angle_gamma                90
_cell_volume                     2369.5(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5298
_cell_measurement_temperature    150.00
_cell_measurement_theta_max      67.406
_cell_measurement_theta_min      4.381
_shelx_estimated_absorpt_T_max   0.997
_shelx_estimated_absorpt_T_min   0.974
_exptl_absorpt_coefficient_mu    2.667
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.5589
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016) was used for absorption correction.
wR2(int) was 0.1632 before and 0.0979 after correction.
The Ratio of minimum to maximum transmission is 0.7421.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'dark violet'
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    violet
_exptl_crystal_density_diffrn    1.439
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             1040
_exptl_crystal_size_max          0.01
_exptl_crystal_size_mid          0.001
_exptl_crystal_size_min          0.001
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1503
_diffrn_reflns_av_unetI/netI     0.0623
_diffrn_reflns_Laue_measured_fraction_full 0.978
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            33994
_diffrn_reflns_point_group_measured_fraction_full 0.978
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_theta_full        50.431
_diffrn_reflns_theta_max         50.431
_diffrn_reflns_theta_min         4.381
_diffrn_ambient_temperature      150.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.978
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_device_type  BrukerD8
_diffrn_measurement_method       ?
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1921
_reflns_number_total             2435
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _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       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.515
_refine_diff_density_min         -0.770
_refine_diff_density_rms         0.112
_refine_ls_extinction_coef       0.0033(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     299
_refine_ls_number_reflns         2435
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0897
_refine_ls_R_factor_gt           0.0733
_refine_ls_restrained_S_all      1.044
_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)+(0.1309P)²+6.5801P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1962
_refine_ls_wR_factor_ref         0.2098
_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) groups
2.a Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), N2(H2), C25(H25), C24(H24), C5(H5), C6(H6), C17(H17), C18(H18),
 C19(H19), C20(H20), C8(H8), C27(H27), C26(H26)
;
_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
Br1 Br 0.10541(12) 0.58516(5) 0.25651(11) 0.0755(6) Uani 1 1 d . . . . .
O3 O 0.6173(5) 0.3698(3) 0.4190(5) 0.0432(14) Uani 1 1 d . . . . .
O2 O 0.1986(5) 0.3290(2) 0.6709(4) 0.0326(12) Uani 1 1 d . . . . .
O1 O -0.0127(5) 0.2450(3) 0.4813(4) 0.0354(13) Uani 1 1 d . . . . .
N1 N -0.1021(6) 0.3497(3) 0.4338(6) 0.0371(16) Uani 1 1 d . . . . .
H1 H -0.175786 0.344268 0.450175 0.044 Uiso 1 1 calc R U . . .
N2 N 0.1406(6) 0.3133(3) 0.2125(5) 0.0330(15) Uani 1 1 d . . . . .
H2 H 0.087504 0.318633 0.136133 0.040 Uiso 1 1 calc R U . . .
C25 C 0.4664(10) 0.4035(4) 0.0286(8) 0.051(2) Uani 1 1 d . . . . .
H25 H 0.514957 0.421631 -0.015938 0.061 Uiso 1 1 calc R U . . .
C24 C 0.5351(9) 0.3949(4) 0.1496(7) 0.045(2) Uani 1 1 d . . . . .
H24 H 0.630141 0.405586 0.189443 0.054 Uiso 1 1 calc R U . . .
C22 C 0.4579(8) 0.3695(4) 0.2119(7) 0.036(2) Uani 1 1 d . . . . .
C21 C 0.5041(9) 0.3583(4) 0.3440(8) 0.040(2) Uani 1 1 d . . . . .
C11 C 0.3769(7) 0.3334(3) 0.3592(7) 0.0323(19) Uani 1 1 d . . . . .
C12 C 0.3643(7) 0.3219(3) 0.4705(7) 0.0309(18) Uani 1 1 d . . . . .
C13 C 0.2444(7) 0.3223(3) 0.4909(7) 0.0297(18) Uani 1 1 d . . . . .
C4 C 0.0990(7) 0.3294(3) 0.4006(6) 0.0289(18) Uani 1 1 d . . . . .
C3 C 0.0494(7) 0.3999(3) 0.3698(6) 0.0303(18) Uani 1 1 d . . . . .
C2 C -0.0716(8) 0.4093(4) 0.3903(6) 0.0340(19) Uani 1 1 d . . . . .
C5 C -0.1379(8) 0.4681(4) 0.3721(7) 0.039(2) Uani 1 1 d . . . . .
H5 H -0.219123 0.473317 0.387572 0.046 Uiso 1 1 calc R U . . .
C6 C -0.0855(8) 0.5196(4) 0.3311(7) 0.044(2) Uani 1 1 d . . . . .
H6 H -0.131159 0.561264 0.317074 0.052 Uiso 1 1 calc R U . . .
C14 C 0.2780(8) 0.3222(3) 0.6204(7) 0.0320(18) Uani 1 1 d . . . . .
C15 C 0.4301(7) 0.3133(3) 0.6800(7) 0.0320(19) Uani 1 1 d . . . . .
C17 C 0.5136(8) 0.3045(4) 0.7987(7) 0.039(2) Uani 1 1 d . . . . .
H17 H 0.476653 0.307025 0.858630 0.046 Uiso 1 1 calc R U . . .
C18 C 0.6504(8) 0.2920(4) 0.8292(7) 0.042(2) Uani 1 1 d . . . . .
H18 H 0.710559 0.287486 0.911186 0.050 Uiso 1 1 calc R U . . .
C19 C 0.7009(9) 0.2860(4) 0.7417(8) 0.046(2) Uani 1 1 d . . . . .
H19 H 0.795597 0.275190 0.764568 0.056 Uiso 1 1 calc R U . . .
C20 C 0.6207(8) 0.2949(4) 0.6222(7) 0.040(2) Uani 1 1 d . . . . .
H20 H 0.658103 0.290318 0.562885 0.048 Uiso 1 1 calc R U . . .
C16 C 0.4825(8) 0.3108(4) 0.5916(7) 0.0337(19) Uani 1 1 d . . . . .
C8 C 0.1046(8) 0.4523(4) 0.3313(7) 0.037(2) Uani 1 1 d . . . . .
H8 H 0.188532 0.447625 0.320052 0.045 Uiso 1 1 calc R U . . .
C7 C 0.0344(8) 0.5122(4) 0.3094(7) 0.042(2) Uani 1 1 d . . . . .
C1 C -0.0092(7) 0.3018(4) 0.4482(6) 0.0322(19) Uani 1 1 d . . . . .
C9 C 0.0745(7) 0.2863(4) 0.2867(7) 0.0335(19) Uani 1 1 d . . . . .
H9A H 0.110209 0.241095 0.312231 0.040 Uiso 1 1 calc R U . . .
H9B H -0.026002 0.282875 0.238697 0.040 Uiso 1 1 calc R U . . .
C10 C 0.2703(8) 0.3310(3) 0.2448(7) 0.0311(18) Uani 1 1 d . . . . .
C23 C 0.3217(8) 0.3534(4) 0.1532(7) 0.036(2) Uani 1 1 d . . . . .
C27 C 0.2541(8) 0.3618(4) 0.0308(7) 0.037(2) Uani 1 1 d . . . . .
H27 H 0.159291 0.350648 -0.009512 0.044 Uiso 1 1 calc R U . . .
C26 C 0.3292(9) 0.3869(4) -0.0311(8) 0.045(2) Uani 1 1 d . . . . .
H26 H 0.285886 0.392812 -0.115484 0.054 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
Br1 C7 1.875(7) . ?
O3 C21 1.205(10) . ?
O2 C14 1.222(8) . ?
O1 C1 1.219(9) . ?
N1 H1 0.8800 . ?
N1 C2 1.401(10) . ?
N1 C1 1.338(10) . ?
N2 H2 0.8800 . ?
N2 C9 1.443(9) . ?
N2 C10 1.313(9) . ?
C25 H25 0.9500 . ?
C25 C24 1.368(12) . ?
C25 C26 1.380(12) . ?
C24 H24 0.9500 . ?
C24 C22 1.405(11) . ?
C22 C21 1.496(12) . ?
C22 C23 1.367(11) . ?
C21 C11 1.509(11) . ?
C11 C12 1.424(10) . ?
C11 C10 1.401(11) . ?
C12 C13 1.379(9) . ?
C12 C16 1.524(10) . ?
C13 C4 1.499(10) . ?
C13 C14 1.466(11) . ?
C4 C3 1.510(10) . ?
C4 C1 1.568(10) . ?
C4 C9 1.565(10) . ?
C3 C2 1.403(10) . ?
C3 C8 1.374(10) . ?
C2 C5 1.350(10) . ?
C5 H5 0.9500 . ?
C5 C6 1.359(11) . ?
C6 H6 0.9500 . ?
C6 C7 1.395(11) . ?
C14 C15 1.487(10) . ?
C15 C17 1.372(11) . ?
C15 C16 1.385(10) . ?
C17 H17 0.9500 . ?
C17 C18 1.363(11) . ?
C18 H18 0.9500 . ?
C18 C19 1.365(11) . ?
C19 H19 0.9500 . ?
C19 C20 1.372(11) . ?
C20 H20 0.9500 . ?
C20 C16 1.391(10) . ?
C8 H8 0.9500 . ?
C8 C7 1.388(11) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C23 1.485(10) . ?
C23 C27 1.382(11) . ?
C27 H27 0.9500 . ?
C27 C26 1.382(10) . ?
C26 H26 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 N1 H1 123.0 . . ?
C1 N1 H1 123.0 . . ?
C1 N1 C2 114.0(6) . . ?
C9 N2 H2 116.0 . . ?
C10 N2 H2 116.0 . . ?
C10 N2 C9 128.0(6) . . ?
C24 C25 H25 118.8 . . ?
C24 C25 C26 122.4(7) . . ?
C26 C25 H25 118.8 . . ?
C25 C24 H24 121.7 . . ?
C25 C24 C22 116.7(8) . . ?
C22 C24 H24 121.7 . . ?
C24 C22 C21 128.1(7) . . ?
C23 C22 C24 121.1(7) . . ?
C23 C22 C21 110.8(6) . . ?
O3 C21 C22 126.1(7) . . ?
O3 C21 C11 129.4(7) . . ?
C22 C21 C11 104.5(7) . . ?
C12 C11 C21 125.9(7) . . ?
C10 C11 C21 107.2(6) . . ?
C10 C11 C12 126.5(6) . . ?
C11 C12 C16 126.3(6) . . ?
C13 C12 C11 126.9(7) . . ?
C13 C12 C16 106.7(6) . . ?
C12 C13 C4 127.9(6) . . ?
C12 C13 C14 109.8(6) . . ?
C14 C13 C4 122.0(6) . . ?
C13 C4 C3 115.2(6) . . ?
C13 C4 C1 112.2(6) . . ?
C13 C4 C9 111.0(5) . . ?
C3 C4 C1 101.3(6) . . ?
C3 C4 C9 112.6(6) . . ?
C9 C4 C1 103.6(5) . . ?
C2 C3 C4 109.6(6) . . ?
C8 C3 C4 131.1(6) . . ?
C8 C3 C2 119.3(7) . . ?
N1 C2 C3 107.9(6) . . ?
C5 C2 N1 129.5(7) . . ?
C5 C2 C3 122.6(7) . . ?
C2 C5 H5 120.9 . . ?
C2 C5 C6 118.2(7) . . ?
C6 C5 H5 120.9 . . ?
C5 C6 H6 119.5 . . ?
C5 C6 C7 120.9(7) . . ?
C7 C6 H6 119.5 . . ?
O2 C14 C13 127.6(7) . . ?
O2 C14 C15 126.0(7) . . ?
C13 C14 C15 106.4(6) . . ?
C17 C15 C14 130.5(6) . . ?
C17 C15 C16 121.4(7) . . ?
C16 C15 C14 108.0(6) . . ?
C15 C17 H17 120.6 . . ?
C18 C17 C15 118.8(7) . . ?
C18 C17 H17 120.6 . . ?
C17 C18 H18 120.1 . . ?
C17 C18 C19 119.9(8) . . ?
C19 C18 H18 120.1 . . ?
C18 C19 H19 118.6 . . ?
C18 C19 C20 122.9(7) . . ?
C20 C19 H19 118.6 . . ?
C19 C20 H20 121.4 . . ?
C19 C20 C16 117.2(7) . . ?
C16 C20 H20 121.4 . . ?
C15 C16 C12 108.5(6) . . ?
C15 C16 C20 119.6(7) . . ?
C20 C16 C12 131.7(7) . . ?
C3 C8 H8 121.0 . . ?
C3 C8 C7 118.1(7) . . ?
C7 C8 H8 121.0 . . ?
C6 C7 Br1 119.5(6) . . ?
C8 C7 Br1 119.7(6) . . ?
C8 C7 C6 120.8(7) . . ?
O1 C1 N1 127.4(6) . . ?
O1 C1 C4 125.2(7) . . ?
N1 C1 C4 107.1(7) . . ?
N2 C9 C4 112.8(6) . . ?
N2 C9 H9A 109.0 . . ?
N2 C9 H9B 109.0 . . ?
C4 C9 H9A 109.0 . . ?
C4 C9 H9B 109.0 . . ?
H9A C9 H9B 107.8 . . ?
N2 C10 C11 129.8(7) . . ?
N2 C10 C23 120.1(7) . . ?
C11 C10 C23 110.1(6) . . ?
C22 C23 C10 107.4(7) . . ?
C22 C23 C27 121.6(7) . . ?
C27 C23 C10 131.0(7) . . ?
C23 C27 H27 121.2 . . ?
C26 C27 C23 117.7(7) . . ?
C26 C27 H27 121.2 . . ?
C25 C26 C27 120.6(8) . . ?
C25 C26 H26 119.7 . . ?
C27 C26 H26 119.7 . . ?

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
O3 C21 C11 C12 3.9(12) . . . . ?
O3 C21 C11 C10 177.5(8) . . . . ?
O2 C14 C15 C17 6.9(12) . . . . ?
O2 C14 C15 C16 -176.9(7) . . . . ?
N1 C2 C5 C6 178.5(7) . . . . ?
N2 C10 C23 C22 179.0(6) . . . . ?
N2 C10 C23 C27 2.0(12) . . . . ?
C25 C24 C22 C21 -176.7(7) . . . . ?
C25 C24 C22 C23 1.0(12) . . . . ?
C24 C25 C26 C27 1.4(13) . . . . ?
C24 C22 C21 O3 0.2(13) . . . . ?
C24 C22 C21 C11 177.6(7) . . . . ?
C24 C22 C23 C10 -177.7(7) . . . . ?
C24 C22 C23 C27 -0.4(12) . . . . ?
C22 C21 C11 C12 -173.3(7) . . . . ?
C22 C21 C11 C10 0.2(8) . . . . ?
C22 C23 C27 C26 0.2(11) . . . . ?
C21 C22 C23 C10 0.4(8) . . . . ?
C21 C22 C23 C27 177.7(7) . . . . ?
C21 C11 C12 C13 155.2(7) . . . . ?
C21 C11 C12 C16 -21.0(11) . . . . ?
C21 C11 C10 N2 -179.1(7) . . . . ?
C21 C11 C10 C23 0.0(8) . . . . ?
C11 C12 C13 C4 5.3(11) . . . . ?
C11 C12 C13 C14 -168.2(6) . . . . ?
C11 C12 C16 C15 169.5(7) . . . . ?
C11 C12 C16 C20 -15.7(12) . . . . ?
C11 C10 C23 C22 -0.2(8) . . . . ?
C11 C10 C23 C27 -177.2(8) . . . . ?
C12 C11 C10 N2 -5.6(12) . . . . ?
C12 C11 C10 C23 173.5(7) . . . . ?
C12 C13 C4 C3 -86.1(8) . . . . ?
C12 C13 C4 C1 158.7(7) . . . . ?
C12 C13 C4 C9 43.3(9) . . . . ?
C12 C13 C14 O2 172.0(6) . . . . ?
C12 C13 C14 C15 -6.8(7) . . . . ?
C13 C12 C16 C15 -7.3(8) . . . . ?
C13 C12 C16 C20 167.5(8) . . . . ?
C13 C4 C3 C2 -124.2(6) . . . . ?
C13 C4 C3 C8 53.6(10) . . . . ?
C13 C4 C1 O1 -58.6(9) . . . . ?
C13 C4 C1 N1 127.5(6) . . . . ?
C13 C4 C9 N2 -73.0(8) . . . . ?
C13 C14 C15 C17 -174.2(7) . . . . ?
C13 C14 C15 C16 2.0(7) . . . . ?
C4 C13 C14 O2 -1.9(11) . . . . ?
C4 C13 C14 C15 179.2(6) . . . . ?
C4 C3 C2 N1 0.8(8) . . . . ?
C4 C3 C2 C5 179.0(7) . . . . ?
C4 C3 C8 C7 179.8(7) . . . . ?
C3 C4 C1 O1 178.0(7) . . . . ?
C3 C4 C1 N1 4.1(7) . . . . ?
C3 C4 C9 N2 57.8(8) . . . . ?
C3 C2 C5 C6 0.8(11) . . . . ?
C3 C8 C7 Br1 -179.9(5) . . . . ?
C3 C8 C7 C6 2.8(12) . . . . ?
C2 N1 C1 O1 -177.8(7) . . . . ?
C2 N1 C1 C4 -4.1(8) . . . . ?
C2 C3 C8 C7 -2.6(11) . . . . ?
C2 C5 C6 C7 -0.6(11) . . . . ?
C5 C6 C7 Br1 -178.5(6) . . . . ?
C5 C6 C7 C8 -1.2(12) . . . . ?
C14 C13 C4 C3 86.7(8) . . . . ?
C14 C13 C4 C1 -28.5(9) . . . . ?
C14 C13 C4 C9 -143.9(6) . . . . ?
C14 C15 C17 C18 174.7(7) . . . . ?
C14 C15 C16 C12 3.1(8) . . . . ?
C14 C15 C16 C20 -172.4(6) . . . . ?
C15 C17 C18 C19 -2.5(11) . . . . ?
C17 C15 C16 C12 179.7(7) . . . . ?
C17 C15 C16 C20 4.2(11) . . . . ?
C17 C18 C19 C20 3.0(12) . . . . ?
C18 C19 C20 C16 0.1(12) . . . . ?
C19 C20 C16 C12 -177.9(7) . . . . ?
C19 C20 C16 C15 -3.6(11) . . . . ?
C16 C12 C13 C4 -177.9(6) . . . . ?
C16 C12 C13 C14 8.6(7) . . . . ?
C16 C15 C17 C18 -1.1(11) . . . . ?
C8 C3 C2 N1 -177.3(7) . . . . ?
C8 C3 C2 C5 0.9(11) . . . . ?
C1 N1 C2 C3 2.2(8) . . . . ?
C1 N1 C2 C5 -175.8(7) . . . . ?
C1 C4 C3 C2 -2.9(7) . . . . ?
C1 C4 C3 C8 174.9(7) . . . . ?
C1 C4 C9 N2 166.4(6) . . . . ?
C9 N2 C10 C11 -5.4(12) . . . . ?
C9 N2 C10 C23 175.6(6) . . . . ?
C9 C4 C3 C2 107.1(7) . . . . ?
C9 C4 C3 C8 -75.1(9) . . . . ?
C9 C4 C1 O1 61.2(9) . . . . ?
C9 C4 C1 N1 -112.7(6) . . . . ?
C10 N2 C9 C4 52.3(9) . . . . ?
C10 C11 C12 C13 -17.1(11) . . . . ?
C10 C11 C12 C16 166.7(7) . . . . ?
C10 C23 C27 C26 176.8(7) . . . . ?
C23 C22 C21 O3 -177.8(7) . . . . ?
C23 C22 C21 C11 -0.4(8) . . . . ?
C23 C27 C26 C25 -0.7(12) . . . . ?
C26 C25 C24 C22 -1.5(13) . . . . ?

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 -0.490 0.000 -0.990 258.9 14.0 '2 H2O'
2 -0.787 0.500 -0.787 258.9 14.0 '2 H2O'

_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_gwg23jc03_auto
_database_code_depnum_ccdc_archive 'CCDC 2390185'
loop_
_audit_author_name
_audit_author_address
'Jack Clegg'
;The University of Queensalnd
Australia
;
_audit_update_record             
;
2024-10-11 deposited with the CCDC.	2024-11-27 downloaded from the CCDC.
;
_audit_creation_date             2024-10-11
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.01.12 svn.r2f8d729c for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C27 H16 N2 O3, H2 O, 1[C1H4O]'
_chemical_formula_sum            'C28 H22 N2 O5'
_chemical_formula_weight         466.47
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C26 H15 N O5'
_chemical_oxdiff_usercomment     SD2
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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           15
_space_group_name_H-M_alt        'I 1 2/a 1'
_space_group_name_Hall           '-I 2ya'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z'
'-x+1/2, -y+1/2, -z+1/2'
'x, -y+1/2, z+1/2'

_cell_length_a                   23.0157(11)
_cell_length_b                   7.5409(3)
_cell_length_c                   27.2889(15)
_cell_angle_alpha                90
_cell_angle_beta                 110.155(6)
_cell_angle_gamma                90
_cell_volume                     4446.2(4)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    2630
_cell_measurement_temperature    190(2)
_cell_measurement_theta_max      27.7000
_cell_measurement_theta_min      2.8790
_shelx_estimated_absorpt_T_max   0.995
_shelx_estimated_absorpt_T_min   0.972
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.52233
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.123a (Rigaku Oxford Diffraction, 2022)
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    1.394
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             1952
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0421
_diffrn_reflns_av_unetI/netI     0.0557
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            10491
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.122
_diffrn_reflns_theta_max         25.122
_diffrn_reflns_theta_min         2.816
_diffrn_ambient_temperature      190(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0434
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -50.00  33.00   1.00   75.00    --   19.52 -38.00-120.00   83
  2  ω     -8.00  83.00   1.00   75.00    --   19.52  19.00-120.00   91
  3  ω    -12.00  15.00   1.00   75.00    --   19.52 -77.00  30.00   27
  4  ω    -79.00 -40.00   1.00   75.00    --  -20.77-178.00   0.00   39
  5  ω    -91.00 -45.00   1.00   75.00    --  -20.77-178.00-120.00   46
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, EosS2, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0124247000
_diffrn_orient_matrix_UB_12      -0.0679455000
_diffrn_orient_matrix_UB_13      -0.0114241000
_diffrn_orient_matrix_UB_21      -0.0139157000
_diffrn_orient_matrix_UB_22      0.0395306000
_diffrn_orient_matrix_UB_23      -0.0248888000
_diffrn_orient_matrix_UB_31      0.0270219000
_diffrn_orient_matrix_UB_32      0.0516439000
_diffrn_orient_matrix_UB_33      0.0040048000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2850
_reflns_number_total             3941
_reflns_odcompleteness_completeness 99.85
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     28.22
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _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 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.135
_refine_diff_density_min         -0.173
_refine_diff_density_rms         0.041
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     305
_refine_ls_number_reflns         3941
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0724
_refine_ls_R_factor_gt           0.0469
_refine_ls_restrained_S_all      1.010
_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)+(0.0508P)²+0.2033P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1043
_refine_ls_wR_factor_ref         0.1160
_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) groups
 At 1.5 times of:
  All O(H) groups
2. Restrained distances
 O4-H4B
 0.87 with sigma of 0.02
3.a Free rotating group:
 O4(H4A)
3.b Secondary CH2 refined with riding coordinates:
 C18(H18A,H18B)
3.c Aromatic/amide H refined with riding coordinates:
 N1(H1), N2(H2), C14(H14), C17(H17), C5(H5), C27(H27), C8(H8), C16(H16),
 C15(H15), C26(H26), C24(H24), C6(H6), C25(H25), C7(H7)
;
_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 0.29770(6) 0.48422(19) 0.22017(5) 0.0397(4) Uani 1 1 d . . . . .
O2 O 0.36940(6) 0.16352(18) 0.27987(6) 0.0386(4) Uani 1 1 d . . . . .
N1 N 0.25115(7) 0.4335(2) 0.28094(7) 0.0346(4) Uani 1 1 d . . . . .
H1 H 0.213746 0.408069 0.259409 0.042 Uiso 1 1 calc R U . . .
O3 O 0.60162(7) 0.6006(2) 0.42553(7) 0.0625(5) Uani 1 1 d . . . . .
N2 N 0.39669(7) 0.8289(2) 0.35087(7) 0.0378(4) Uani 1 1 d . . . . .
H2 H 0.379254 0.914520 0.362814 0.045 Uiso 1 1 calc R U . . .
O4 O 0.30524(9) 1.0115(3) 0.37420(8) 0.0668(5) Uani 1 1 d DG . . . .
H4A H 0.273648 1.024004 0.346802 0.100 Uiso 1 1 d G U . . .
C10 C 0.41427(8) 0.2623(3) 0.29864(7) 0.0290(5) Uani 1 1 d . . . . .
C9 C 0.41380(8) 0.4413(3) 0.31847(7) 0.0273(4) Uani 1 1 d . . . . .
C13 C 0.47376(8) 0.4999(3) 0.34222(7) 0.0285(5) Uani 1 1 d . . . . .
C11 C 0.47964(8) 0.2174(3) 0.30693(7) 0.0297(5) Uani 1 1 d . . . . .
C1 C 0.29920(8) 0.4757(3) 0.26539(8) 0.0304(5) Uani 1 1 d . . . . .
C2 C 0.35417(8) 0.5310(3) 0.31428(7) 0.0291(5) Uani 1 1 d . . . . .
C20 C 0.49382(8) 0.6591(3) 0.37189(7) 0.0306(5) Uani 1 1 d . . . . .
C3 C 0.32931(9) 0.4887(3) 0.35760(8) 0.0303(5) Uani 1 1 d . . . . .
C12 C 0.51599(8) 0.3609(3) 0.33234(7) 0.0313(5) Uani 1 1 d . . . . .
C23 C 0.49179(9) 0.9326(3) 0.41457(8) 0.0339(5) Uani 1 1 d . . . . .
C4 C 0.26793(9) 0.4350(3) 0.33533(8) 0.0330(5) Uani 1 1 d . . . . .
C19 C 0.45615(9) 0.8007(3) 0.37587(8) 0.0319(5) Uani 1 1 d . . . . .
C22 C 0.55167(9) 0.8696(3) 0.43565(8) 0.0366(5) Uani 1 1 d . . . . .
C18 C 0.35745(9) 0.7331(3) 0.30588(8) 0.0363(5) Uani 1 1 d . . . . .
H18A H 0.372695 0.753151 0.276546 0.044 Uiso 1 1 calc R U . . .
H18B H 0.315086 0.782537 0.295592 0.044 Uiso 1 1 calc R U . . .
C14 C 0.50342(9) 0.0698(3) 0.29138(8) 0.0387(5) Uani 1 1 d . . . . .
H14 H 0.477448 -0.026054 0.274478 0.046 Uiso 1 1 calc R U . . .
C17 C 0.57871(9) 0.3574(3) 0.34045(8) 0.0410(6) Uani 1 1 d . . . . .
H17 H 0.604509 0.454756 0.356384 0.049 Uiso 1 1 calc R U . . .
C5 C 0.35717(10) 0.4880(3) 0.41100(8) 0.0402(5) Uani 1 1 d . . . . .
H5 H 0.399393 0.520823 0.426722 0.048 Uiso 1 1 calc R U . . .
C27 C 0.47549(10) 1.0957(3) 0.42872(9) 0.0427(6) Uani 1 1 d . . . . .
H27 H 0.434570 1.140375 0.413658 0.051 Uiso 1 1 calc R U . . .
C21 C 0.55555(9) 0.6948(3) 0.41169(8) 0.0394(5) Uani 1 1 d . . . . .
C8 C 0.23251(10) 0.3864(3) 0.36488(10) 0.0464(6) Uani 1 1 d . . . . .
H8 H 0.190435 0.352240 0.349047 0.056 Uiso 1 1 calc R U . . .
C16 C 0.60327(9) 0.2070(3) 0.32463(8) 0.0479(6) Uani 1 1 d . . . . .
H16 H 0.646361 0.203312 0.330288 0.057 Uiso 1 1 calc R U . . .
C15 C 0.56719(10) 0.0650(3) 0.30123(8) 0.0470(6) Uani 1 1 d . . . . .
H15 H 0.585438 -0.036393 0.291737 0.056 Uiso 1 1 calc R U . . .
C26 C 0.52136(11) 1.1924(3) 0.46593(9) 0.0489(6) Uani 1 1 d . . . . .
H26 H 0.511551 1.305262 0.476477 0.059 Uiso 1 1 calc R U . . .
C24 C 0.59664(10) 0.9637(3) 0.47301(9) 0.0500(6) Uani 1 1 d . . . . .
H24 H 0.637380 0.917925 0.488295 0.060 Uiso 1 1 calc R U . . .
C6 C 0.32233(12) 0.4382(3) 0.44173(10) 0.0520(6) Uani 1 1 d . . . . .
H6 H 0.340883 0.437666 0.478683 0.062 Uiso 1 1 calc R U . . .
C25 C 0.58071(11) 1.1276(3) 0.48774(10) 0.0534(7) Uani 1 1 d . . . . .
H25 H 0.611102 1.195975 0.513182 0.064 Uiso 1 1 calc R U . . .
C7 C 0.26092(12) 0.3896(3) 0.41864(10) 0.0556(7) Uani 1 1 d . . . . .
H7 H 0.237723 0.357730 0.440133 0.067 Uiso 1 1 calc R U . . .
H4B H 0.299(2) 1.068(6) 0.3991(13) 0.18(2) Uiso 1 1 d D . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.224(2) . ?
O2 C10 1.232(2) . ?
N1 H1 0.8800 . ?
N1 C1 1.352(2) . ?
N1 C4 1.399(3) . ?
O3 C21 1.223(2) . ?
N2 H2 0.8800 . ?
N2 C19 1.319(2) . ?
N2 C18 1.443(2) . ?
O4 H4A 0.8497 . ?
O4 H4B 0.853(19) . ?
C10 C9 1.456(3) . ?
C10 C11 1.481(3) . ?
C9 C13 1.379(3) . ?
C9 C2 1.499(3) . ?
C13 C20 1.433(3) . ?
C13 C12 1.516(3) . ?
C11 C12 1.397(3) . ?
C11 C14 1.370(3) . ?
C1 C2 1.546(3) . ?
C2 C3 1.514(3) . ?
C2 C18 1.547(3) . ?
C20 C19 1.403(3) . ?
C20 C21 1.485(3) . ?
C3 C4 1.392(3) . ?
C3 C5 1.375(3) . ?
C12 C17 1.383(3) . ?
C23 C19 1.477(3) . ?
C23 C22 1.382(3) . ?
C23 C27 1.380(3) . ?
C4 C8 1.379(3) . ?
C22 C21 1.488(3) . ?
C22 C24 1.374(3) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C14 H14 0.9500 . ?
C14 C15 1.399(3) . ?
C17 H17 0.9500 . ?
C17 C16 1.400(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.397(3) . ?
C27 H27 0.9500 . ?
C27 C26 1.392(3) . ?
C8 H8 0.9500 . ?
C8 C7 1.385(3) . ?
C16 H16 0.9500 . ?
C16 C15 1.371(3) . ?
C15 H15 0.9500 . ?
C26 H26 0.9500 . ?
C26 C25 1.378(3) . ?
C24 H24 0.9500 . ?
C24 C25 1.388(3) . ?
C6 H6 0.9500 . ?
C6 C7 1.384(3) . ?
C25 H25 0.9500 . ?
C7 H7 0.9500 . ?

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
C1 N1 H1 124.0 . . ?
C1 N1 C4 111.99(16) . . ?
C4 N1 H1 124.0 . . ?
C19 N2 H2 116.8 . . ?
C19 N2 C18 126.38(18) . . ?
C18 N2 H2 116.8 . . ?
H4A O4 H4B 108.6 . . ?
O2 C10 C9 127.04(17) . . ?
O2 C10 C11 125.92(18) . . ?
C9 C10 C11 107.01(16) . . ?
C10 C9 C2 120.92(16) . . ?
C13 C9 C10 109.70(16) . . ?
C13 C9 C2 129.28(18) . . ?
C9 C13 C20 127.53(18) . . ?
C9 C13 C12 107.10(17) . . ?
C20 C13 C12 125.36(16) . . ?
C12 C11 C10 107.55(17) . . ?
C14 C11 C10 129.15(18) . . ?
C14 C11 C12 123.22(17) . . ?
O1 C1 N1 125.93(18) . . ?
O1 C1 C2 125.87(17) . . ?
N1 C1 C2 107.89(17) . . ?
C9 C2 C1 113.57(16) . . ?
C9 C2 C3 115.33(16) . . ?
C9 C2 C18 111.43(16) . . ?
C1 C2 C18 101.84(15) . . ?
C3 C2 C1 101.53(15) . . ?
C3 C2 C18 111.97(17) . . ?
C13 C20 C21 127.27(18) . . ?
C19 C20 C13 126.44(17) . . ?
C19 C20 C21 105.47(17) . . ?
C4 C3 C2 108.66(17) . . ?
C5 C3 C2 131.64(18) . . ?
C5 C3 C4 119.62(19) . . ?
C11 C12 C13 108.24(16) . . ?
C17 C12 C13 133.03(19) . . ?
C17 C12 C11 118.58(19) . . ?
C22 C23 C19 107.14(18) . . ?
C27 C23 C19 131.55(19) . . ?
C27 C23 C22 121.23(19) . . ?
C3 C4 N1 109.47(17) . . ?
C8 C4 N1 127.98(19) . . ?
C8 C4 C3 122.5(2) . . ?
N2 C19 C20 129.89(18) . . ?
N2 C19 C23 118.88(18) . . ?
C20 C19 C23 111.23(16) . . ?
C23 C22 C21 108.90(17) . . ?
C24 C22 C23 121.3(2) . . ?
C24 C22 C21 129.8(2) . . ?
N2 C18 C2 114.55(16) . . ?
N2 C18 H18A 108.6 . . ?
N2 C18 H18B 108.6 . . ?
C2 C18 H18A 108.6 . . ?
C2 C18 H18B 108.6 . . ?
H18A C18 H18B 107.6 . . ?
C11 C14 H14 121.1 . . ?
C11 C14 C15 117.8(2) . . ?
C15 C14 H14 121.1 . . ?
C12 C17 H17 120.8 . . ?
C12 C17 C16 118.4(2) . . ?
C16 C17 H17 120.8 . . ?
C3 C5 H5 120.6 . . ?
C3 C5 C6 118.9(2) . . ?
C6 C5 H5 120.6 . . ?
C23 C27 H27 121.3 . . ?
C23 C27 C26 117.4(2) . . ?
C26 C27 H27 121.3 . . ?
O3 C21 C20 129.0(2) . . ?
O3 C21 C22 123.76(19) . . ?
C20 C21 C22 107.13(17) . . ?
C4 C8 H8 121.4 . . ?
C4 C8 C7 117.1(2) . . ?
C7 C8 H8 121.4 . . ?
C17 C16 H16 118.9 . . ?
C15 C16 C17 122.17(19) . . ?
C15 C16 H16 118.9 . . ?
C14 C15 H15 120.1 . . ?
C16 C15 C14 119.8(2) . . ?
C16 C15 H15 120.1 . . ?
C27 C26 H26 119.4 . . ?
C25 C26 C27 121.3(2) . . ?
C25 C26 H26 119.4 . . ?
C22 C24 H24 121.0 . . ?
C22 C24 C25 117.9(2) . . ?
C25 C24 H24 121.0 . . ?
C5 C6 H6 119.8 . . ?
C7 C6 C5 120.4(2) . . ?
C7 C6 H6 119.8 . . ?
C26 C25 C24 120.8(2) . . ?
C26 C25 H25 119.6 . . ?
C24 C25 H25 119.6 . . ?
C8 C7 H7 119.3 . . ?
C6 C7 C8 121.5(2) . . ?
C6 C7 H7 119.3 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C9 -55.0(3) . . . . ?
O1 C1 C2 C3 -179.38(19) . . . . ?
O1 C1 C2 C18 65.0(2) . . . . ?
O2 C10 C9 C13 172.42(19) . . . . ?
O2 C10 C9 C2 -4.3(3) . . . . ?
O2 C10 C11 C12 -175.84(18) . . . . ?
O2 C10 C11 C14 7.3(3) . . . . ?
N1 C1 C2 C9 131.13(17) . . . . ?
N1 C1 C2 C3 6.7(2) . . . . ?
N1 C1 C2 C18 -108.94(18) . . . . ?
N1 C4 C8 C7 176.2(2) . . . . ?
C10 C9 C13 C20 -172.11(19) . . . . ?
C10 C9 C13 C12 6.5(2) . . . . ?
C10 C9 C2 C1 -31.9(2) . . . . ?
C10 C9 C2 C3 84.7(2) . . . . ?
C10 C9 C2 C18 -146.22(18) . . . . ?
C10 C11 C12 C13 1.6(2) . . . . ?
C10 C11 C12 C17 -174.45(17) . . . . ?
C10 C11 C14 C15 175.8(2) . . . . ?
C9 C10 C11 C12 2.2(2) . . . . ?
C9 C10 C11 C14 -174.62(19) . . . . ?
C9 C13 C20 C19 -10.8(3) . . . . ?
C9 C13 C20 C21 157.3(2) . . . . ?
C9 C13 C12 C11 -5.1(2) . . . . ?
C9 C13 C12 C17 170.2(2) . . . . ?
C9 C2 C3 C4 -128.27(18) . . . . ?
C9 C2 C3 C5 48.5(3) . . . . ?
C9 C2 C18 N2 -70.7(2) . . . . ?
C13 C9 C2 C1 152.12(19) . . . . ?
C13 C9 C2 C3 -91.3(2) . . . . ?
C13 C9 C2 C18 37.8(3) . . . . ?
C13 C20 C19 N2 -6.6(3) . . . . ?
C13 C20 C19 C23 173.47(18) . . . . ?
C13 C20 C21 O3 3.1(4) . . . . ?
C13 C20 C21 C22 -173.83(19) . . . . ?
C13 C12 C17 C16 -177.4(2) . . . . ?
C11 C10 C9 C13 -5.6(2) . . . . ?
C11 C10 C9 C2 177.70(16) . . . . ?
C11 C12 C17 C16 -2.5(3) . . . . ?
C11 C14 C15 C16 -1.5(3) . . . . ?
C1 N1 C4 C3 2.9(2) . . . . ?
C1 N1 C4 C8 -174.8(2) . . . . ?
C1 C2 C3 C4 -5.0(2) . . . . ?
C1 C2 C3 C5 171.7(2) . . . . ?
C1 C2 C18 N2 167.85(16) . . . . ?
C2 C9 C13 C20 4.2(3) . . . . ?
C2 C9 C13 C12 -177.15(18) . . . . ?
C2 C3 C4 N1 1.8(2) . . . . ?
C2 C3 C4 C8 179.68(19) . . . . ?
C2 C3 C5 C6 -178.4(2) . . . . ?
C20 C13 C12 C11 173.55(18) . . . . ?
C20 C13 C12 C17 -11.2(3) . . . . ?
C3 C2 C18 N2 60.1(2) . . . . ?
C3 C4 C8 C7 -1.2(3) . . . . ?
C3 C5 C6 C7 0.3(3) . . . . ?
C12 C13 C20 C19 170.84(18) . . . . ?
C12 C13 C20 C21 -21.1(3) . . . . ?
C12 C11 C14 C15 -0.6(3) . . . . ?
C12 C17 C16 C15 0.4(3) . . . . ?
C23 C22 C21 O3 -174.2(2) . . . . ?
C23 C22 C21 C20 3.0(2) . . . . ?
C23 C22 C24 C25 -2.2(3) . . . . ?
C23 C27 C26 C25 0.0(3) . . . . ?
C4 N1 C1 O1 179.9(2) . . . . ?
C4 N1 C1 C2 -6.2(2) . . . . ?
C4 C3 C5 C6 -1.9(3) . . . . ?
C4 C8 C7 C6 -0.5(4) . . . . ?
C19 N2 C18 C2 58.1(3) . . . . ?
C19 C20 C21 O3 173.2(2) . . . . ?
C19 C20 C21 C22 -3.7(2) . . . . ?
C19 C23 C22 C21 -1.0(2) . . . . ?
C19 C23 C22 C24 179.6(2) . . . . ?
C19 C23 C27 C26 -177.6(2) . . . . ?
C22 C23 C19 N2 178.57(19) . . . . ?
C22 C23 C19 C20 -1.5(2) . . . . ?
C22 C23 C27 C26 -1.5(3) . . . . ?
C22 C24 C25 C26 0.8(4) . . . . ?
C18 N2 C19 C20 -11.7(3) . . . . ?
C18 N2 C19 C23 168.25(18) . . . . ?
C18 C2 C3 C4 102.91(18) . . . . ?
C18 C2 C3 C5 -80.3(3) . . . . ?
C14 C11 C12 C13 178.70(18) . . . . ?
C14 C11 C12 C17 2.6(3) . . . . ?
C17 C16 C15 C14 1.6(4) . . . . ?
C5 C3 C4 N1 -175.44(18) . . . . ?
C5 C3 C4 C8 2.4(3) . . . . ?
C5 C6 C7 C8 0.9(4) . . . . ?
C27 C23 C19 N2 -4.9(3) . . . . ?
C27 C23 C19 C20 175.1(2) . . . . ?
C27 C23 C22 C21 -177.97(19) . . . . ?
C27 C23 C22 C24 2.6(3) . . . . ?
C27 C26 C25 C24 0.3(4) . . . . ?
C21 C20 C19 N2 -176.8(2) . . . . ?
C21 C20 C19 C23 3.3(2) . . . . ?
C21 C22 C24 C25 178.5(2) . . . . ?
C24 C22 C21 O3 5.1(4) . . . . ?
C24 C22 C21 C20 -177.7(2) . . . . ?

_smtbx_masks_special_details     
;
A solvent mask was calculated and 120 electrons were 
found in a volume of 476Å³ in 1 void per unit cell. 
This is consistent with the presence of 
MeOH per formula unit.
;
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 0.250 -0.122 0.500 118.6 29.5 '2 C1H4O'
2 0.250 0.622 0.000 118.6 29.5 '2 C1H4O'
3 0.750 0.378 1.000 118.6 29.5 '2 C1H4O'
4 0.750 0.122 0.500 118.6 29.5 '2 C1H4O'

_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.471
_oxdiff_exptl_absorpt_empirical_full_min 0.766
####################################################################### 
# 
# 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_swg24jc01
_database_code_depnum_ccdc_archive 'CCDC 2390186'
loop_
_audit_author_name
_audit_author_address
'Jack Clegg'
;The University of Queensalnd
Australia
;
_audit_update_record             
;
2024-10-11 deposited with the CCDC.	2024-11-27 downloaded from the CCDC.
;
_audit_creation_date             2024-10-11
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.01.12 svn.r2f8d729c for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C28 H18 N2 O3, 0.5[C3H6O]'
_chemical_formula_sum            'C29.50 H21 N2 O3.50'
_chemical_formula_weight         459.48
_chemical_melting_point          ?
_chemical_oxdiff_formula         C28H17N2O3
_chemical_oxdiff_usercomment     MeIsatin
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   12.2834(7)
_cell_length_b                   9.2034(5)
_cell_length_c                   20.3095(13)
_cell_angle_alpha                90
_cell_angle_beta                 100.514(6)
_cell_angle_gamma                90
_cell_volume                     2257.4(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7690
_cell_measurement_temperature    219.7(6)
_cell_measurement_theta_max      32.4460
_cell_measurement_theta_min      2.1510
_shelx_estimated_absorpt_T_max   0.982
_shelx_estimated_absorpt_T_min   0.916
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.45317
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.128a (Rigaku Oxford Diffraction, 2024)
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    1.352
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             960
_exptl_crystal_size_max          1
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0508
_diffrn_reflns_av_unetI/netI     0.0489
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            26341
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.282
_diffrn_reflns_theta_min         2.124
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      219.7(6)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_detector_type            'Pilatus 300K'
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -20.00  43.00   0.50    5.00    --    8.20  80.00 -98.00  126
  2  ω      6.00  34.00   0.50    5.00    --    8.20 -80.00 137.00   56
  3  ω    -15.00  43.00   0.50    5.00    --   -9.45  80.00 -98.00  116
  4  ω      3.00  45.00   0.50    5.00    --    8.20 -99.00   0.00   84
  5  ω     14.00  44.00   0.50    5.00    --    8.20 -99.00 -90.00   60
  6  ω     43.00  82.00   0.50    5.00    --    8.20  57.00  90.00   78
  7  ω    -11.00  39.00   0.50    5.00    --    8.20  57.00  90.00  100
  8  ω      1.00  44.00   0.50    5.00    --    8.20 -99.00 -30.00   86
  9  ω    -41.00  -2.00   0.50    5.00    --   -9.45 -57.00 120.00   78
 10  ω    -69.00 -44.00   0.50    5.00    --   -9.45 -57.00 120.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, Pilatus 300K'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0206230000
_diffrn_orient_matrix_UB_12      -0.0618153000
_diffrn_orient_matrix_UB_13      0.0146052000
_diffrn_orient_matrix_UB_21      -0.0276705000
_diffrn_orient_matrix_UB_22      -0.0227879000
_diffrn_orient_matrix_UB_23      -0.0320666000
_diffrn_orient_matrix_UB_31      0.0475159000
_diffrn_orient_matrix_UB_32      -0.0400695000
_diffrn_orient_matrix_UB_33      -0.0043458000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3868
_reflns_number_total             5558
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _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 1.171.43.128a (Rigaku OD, 2024)'
_computing_data_collection       'CrysAlisPro 1.171.43.128a (Rigaku OD, 2024)'
_computing_data_reduction        'CrysAlisPro 1.171.43.128a (Rigaku OD, 2024)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.243
_refine_diff_density_min         -0.249
_refine_diff_density_rms         0.042
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     302
_refine_ls_number_reflns         5558
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0736
_refine_ls_R_factor_gt           0.0483
_refine_ls_restrained_S_all      1.032
_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)+(0.0569P)²+0.2788P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1146
_refine_ls_wR_factor_ref         0.1246
_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,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B)
2.b Aromatic/amide H refined with riding coordinates:
 C8(H8), C28(H28), C27(H27), C7(H7), C16(H16), C5(H5), C25(H25), C19(H19),
 C6(H6), C26(H26), C17(H17), C18(H18)
2.c Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C)
;
_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 0.69417(9) 0.44842(12) 0.13067(5) 0.0446(3) Uani 1 1 d . . . . .
O2 O 0.43305(9) 0.50423(12) 0.11287(6) 0.0461(3) Uani 1 1 d . . . . .
N2 N 0.71265(10) 0.67403(13) 0.32419(6) 0.0312(3) Uani 1 1 d . . . . .
N1 N 0.64453(10) 0.68058(13) 0.09680(6) 0.0330(3) Uani 1 1 d . . . . .
O3 O 0.55729(12) 0.27699(14) 0.42327(6) 0.0653(4) Uani 1 1 d . . . . .
C3 C 0.57688(10) 0.76796(14) 0.18707(7) 0.0280(3) Uani 1 1 d . . . . .
C15 C 0.53137(11) 0.44456(14) 0.28402(7) 0.0277(3) Uani 1 1 d . . . . .
C1 C 0.65683(11) 0.56831(15) 0.14051(7) 0.0313(3) Uani 1 1 d . . . . .
C11 C 0.53956(11) 0.51157(14) 0.22463(7) 0.0275(3) Uani 1 1 d . . . . .
C24 C 0.66918(11) 0.58982(15) 0.36537(7) 0.0290(3) Uani 1 1 d . . . . .
C2 C 0.59516(11) 0.80006(15) 0.12293(7) 0.0305(3) Uani 1 1 d . . . . .
C23 C 0.69901(11) 0.60701(15) 0.43905(7) 0.0320(3) Uani 1 1 d . . . . .
C22 C 0.65378(12) 0.49016(16) 0.46755(7) 0.0365(3) Uani 1 1 d . . . . .
C14 C 0.42885(11) 0.34772(15) 0.27016(8) 0.0317(3) Uani 1 1 d . . . . .
C4 C 0.62178(11) 0.61765(14) 0.20629(7) 0.0266(3) Uani 1 1 d . . . . .
C8 C 0.52683(11) 0.86839(15) 0.22187(8) 0.0353(3) Uani 1 1 d . . . . .
H8 H 0.512489 0.846860 0.265231 0.042 Uiso 1 1 calc R U . . .
C20 C 0.59716(12) 0.47098(15) 0.34895(7) 0.0311(3) Uani 1 1 d . . . . .
C13 C 0.38055(11) 0.36302(15) 0.20287(8) 0.0334(3) Uani 1 1 d . . . . .
C12 C 0.44894(11) 0.46507(15) 0.17157(8) 0.0329(3) Uani 1 1 d . . . . .
C10 C 0.72887(11) 0.62523(16) 0.25866(7) 0.0303(3) Uani 1 1 d . . . . .
H10A H 0.763325 0.527642 0.263261 0.036 Uiso 1 1 calc R U . . .
H10B H 0.781153 0.692104 0.242268 0.036 Uiso 1 1 calc R U . . .
C21 C 0.59337(13) 0.39665(17) 0.41315(8) 0.0398(4) Uani 1 1 d . . . . .
C28 C 0.76614(13) 0.70647(17) 0.47834(8) 0.0401(4) Uani 1 1 d . . . . .
H28 H 0.798148 0.785958 0.458893 0.048 Uiso 1 1 calc R U . . .
C27 C 0.78509(14) 0.68584(19) 0.54742(8) 0.0456(4) Uani 1 1 d . . . . .
H27 H 0.829832 0.753410 0.575646 0.055 Uiso 1 1 calc R U . . .
C7 C 0.49761(12) 1.00276(17) 0.19193(9) 0.0454(4) Uani 1 1 d . . . . .
H7 H 0.463340 1.073741 0.215311 0.054 Uiso 1 1 calc R U . . .
C16 C 0.28354(12) 0.29470(17) 0.17454(9) 0.0426(4) Uani 1 1 d . . . . .
H16 H 0.252295 0.308230 0.128604 0.051 Uiso 1 1 calc R U . . .
C5 C 0.56654(12) 0.93257(16) 0.09282(8) 0.0412(4) Uani 1 1 d . . . . .
H5 H 0.579658 0.953633 0.049144 0.049 Uiso 1 1 calc R U . . .
C25 C 0.67354(14) 0.46920(19) 0.53602(8) 0.0444(4) Uani 1 1 d . . . . .
H25 H 0.642486 0.388808 0.555395 0.053 Uiso 1 1 calc R U . . .
C19 C 0.37811(13) 0.25890(18) 0.30998(9) 0.0442(4) Uani 1 1 d . . . . .
H19 H 0.409127 0.245594 0.355961 0.053 Uiso 1 1 calc R U . . .
C6 C 0.51780(13) 1.03370(17) 0.12903(10) 0.0490(4) Uani 1 1 d . . . . .
H6 H 0.497951 1.126348 0.109935 0.059 Uiso 1 1 calc R U . . .
C26 C 0.74013(14) 0.5692(2) 0.57561(8) 0.0460(4) Uani 1 1 d . . . . .
H26 H 0.754995 0.557158 0.622863 0.055 Uiso 1 1 calc R U . . .
C17 C 0.23271(13) 0.20556(19) 0.21498(10) 0.0503(5) Uani 1 1 d . . . . .
H17 H 0.165802 0.156612 0.196956 0.060 Uiso 1 1 calc R U . . .
C18 C 0.27974(15) 0.1885(2) 0.28123(10) 0.0553(5) Uani 1 1 d . . . . .
H18 H 0.244416 0.127036 0.308471 0.066 Uiso 1 1 calc R U . . .
C9 C 0.65719(16) 0.6649(2) 0.02730(8) 0.0510(4) Uani 1 1 d . . . . .
H9A H 0.703626 0.580091 0.022954 0.077 Uiso 1 1 calc R U . . .
H9B H 0.692245 0.752303 0.013149 0.077 Uiso 1 1 calc R U . . .
H9C H 0.584242 0.651681 -0.001019 0.077 Uiso 1 1 calc R U . . .
H2 H 0.7519(17) 0.759(2) 0.3402(10) 0.077 Uiso 1 1 d . U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.2253(17) . ?
O2 C12 1.2265(18) . ?
N2 C24 1.3221(18) . ?
N2 C10 1.4525(18) . ?
N2 H2 0.94(2) . ?
N1 C1 1.3527(18) . ?
N1 C2 1.4057(18) . ?
N1 C9 1.455(2) . ?
O3 C21 1.2185(19) . ?
C3 C2 1.393(2) . ?
C3 C4 1.5138(18) . ?
C3 C8 1.3748(19) . ?
C15 C11 1.3746(19) . ?
C15 C14 1.5265(19) . ?
C15 C20 1.436(2) . ?
C1 C4 1.5447(19) . ?
C11 C4 1.4998(18) . ?
C11 C12 1.4649(19) . ?
C24 C23 1.4827(19) . ?
C24 C20 1.4080(19) . ?
C2 C5 1.381(2) . ?
C23 C22 1.385(2) . ?
C23 C28 1.384(2) . ?
C22 C21 1.488(2) . ?
C22 C25 1.381(2) . ?
C14 C13 1.394(2) . ?
C14 C19 1.376(2) . ?
C4 C10 1.5348(19) . ?
C8 H8 0.9500 . ?
C8 C7 1.396(2) . ?
C20 C21 1.481(2) . ?
C13 C12 1.479(2) . ?
C13 C16 1.377(2) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C28 H28 0.9500 . ?
C28 C27 1.393(2) . ?
C27 H27 0.9500 . ?
C27 C26 1.379(2) . ?
C7 H7 0.9500 . ?
C7 C6 1.375(2) . ?
C16 H16 0.9500 . ?
C16 C17 1.387(2) . ?
C5 H5 0.9500 . ?
C5 C6 1.388(2) . ?
C25 H25 0.9500 . ?
C25 C26 1.387(2) . ?
C19 H19 0.9500 . ?
C19 C18 1.401(2) . ?
C6 H6 0.9500 . ?
C26 H26 0.9500 . ?
C17 H17 0.9500 . ?
C17 C18 1.373(3) . ?
C18 H18 0.9500 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 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
C24 N2 C10 122.49(12) . . ?
C24 N2 H2 120.4(13) . . ?
C10 N2 H2 115.2(13) . . ?
C1 N1 C2 110.73(12) . . ?
C1 N1 C9 122.81(13) . . ?
C2 N1 C9 125.01(13) . . ?
C2 C3 C4 108.75(11) . . ?
C8 C3 C2 120.10(13) . . ?
C8 C3 C4 131.14(13) . . ?
C11 C15 C14 106.87(12) . . ?
C11 C15 C20 127.65(12) . . ?
C20 C15 C14 125.12(13) . . ?
O1 C1 N1 125.53(13) . . ?
O1 C1 C4 125.28(13) . . ?
N1 C1 C4 109.13(11) . . ?
C15 C11 C4 132.10(12) . . ?
C15 C11 C12 110.30(12) . . ?
C12 C11 C4 117.59(12) . . ?
N2 C24 C23 121.46(12) . . ?
N2 C24 C20 127.90(13) . . ?
C20 C24 C23 110.54(12) . . ?
C3 C2 N1 109.96(12) . . ?
C5 C2 N1 128.04(14) . . ?
C5 C2 C3 122.00(14) . . ?
C22 C23 C24 107.15(12) . . ?
C28 C23 C24 131.62(14) . . ?
C28 C23 C22 121.00(14) . . ?
C23 C22 C21 108.82(13) . . ?
C25 C22 C23 121.28(15) . . ?
C25 C22 C21 129.74(15) . . ?
C13 C14 C15 108.12(12) . . ?
C19 C14 C15 133.25(14) . . ?
C19 C14 C13 118.60(13) . . ?
C3 C4 C1 101.05(11) . . ?
C3 C4 C10 111.28(11) . . ?
C11 C4 C3 115.38(11) . . ?
C11 C4 C1 109.27(11) . . ?
C11 C4 C10 112.85(11) . . ?
C10 C4 C1 105.89(11) . . ?
C3 C8 H8 120.8 . . ?
C3 C8 C7 118.38(15) . . ?
C7 C8 H8 120.8 . . ?
C15 C20 C21 128.87(13) . . ?
C24 C20 C15 124.96(13) . . ?
C24 C20 C21 105.64(12) . . ?
C14 C13 C12 108.18(12) . . ?
C16 C13 C14 122.99(15) . . ?
C16 C13 C12 128.80(14) . . ?
O2 C12 C11 126.44(13) . . ?
O2 C12 C13 127.04(13) . . ?
C11 C12 C13 106.52(12) . . ?
N2 C10 C4 113.93(11) . . ?
N2 C10 H10A 108.8 . . ?
N2 C10 H10B 108.8 . . ?
C4 C10 H10A 108.8 . . ?
C4 C10 H10B 108.8 . . ?
H10A C10 H10B 107.7 . . ?
O3 C21 C22 123.03(14) . . ?
O3 C21 C20 129.56(15) . . ?
C20 C21 C22 107.17(13) . . ?
C23 C28 H28 121.2 . . ?
C23 C28 C27 117.60(15) . . ?
C27 C28 H28 121.2 . . ?
C28 C27 H27 119.4 . . ?
C26 C27 C28 121.24(15) . . ?
C26 C27 H27 119.4 . . ?
C8 C7 H7 119.6 . . ?
C6 C7 C8 120.84(15) . . ?
C6 C7 H7 119.6 . . ?
C13 C16 H16 120.9 . . ?
C13 C16 C17 118.12(16) . . ?
C17 C16 H16 120.9 . . ?
C2 C5 H5 121.4 . . ?
C2 C5 C6 117.20(15) . . ?
C6 C5 H5 121.4 . . ?
C22 C25 H25 121.0 . . ?
C22 C25 C26 117.90(16) . . ?
C26 C25 H25 121.0 . . ?
C14 C19 H19 120.7 . . ?
C14 C19 C18 118.57(16) . . ?
C18 C19 H19 120.7 . . ?
C7 C6 C5 121.46(14) . . ?
C7 C6 H6 119.3 . . ?
C5 C6 H6 119.3 . . ?
C27 C26 C25 120.97(15) . . ?
C27 C26 H26 119.5 . . ?
C25 C26 H26 119.5 . . ?
C16 C17 H17 120.2 . . ?
C18 C17 C16 119.56(15) . . ?
C18 C17 H17 120.2 . . ?
C19 C18 H18 118.9 . . ?
C17 C18 C19 122.17(17) . . ?
C17 C18 H18 118.9 . . ?
N1 C9 H9A 109.5 . . ?
N1 C9 H9B 109.5 . . ?
N1 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C4 C3 -176.59(14) . . . . ?
O1 C1 C4 C11 -54.52(18) . . . . ?
O1 C1 C4 C10 67.29(17) . . . . ?
N2 C24 C23 C22 -170.91(13) . . . . ?
N2 C24 C23 C28 3.4(2) . . . . ?
N2 C24 C20 C15 -19.6(2) . . . . ?
N2 C24 C20 C21 168.06(14) . . . . ?
N1 C1 C4 C3 6.21(14) . . . . ?
N1 C1 C4 C11 128.28(12) . . . . ?
N1 C1 C4 C10 -109.91(12) . . . . ?
N1 C2 C5 C6 179.65(14) . . . . ?
C3 C2 C5 C6 -0.3(2) . . . . ?
C3 C4 C10 N2 69.52(15) . . . . ?
C3 C8 C7 C6 0.4(2) . . . . ?
C15 C11 C4 C3 -113.50(16) . . . . ?
C15 C11 C4 C1 133.51(15) . . . . ?
C15 C11 C4 C10 16.0(2) . . . . ?
C15 C11 C12 O2 -179.58(14) . . . . ?
C15 C11 C12 C13 0.81(15) . . . . ?
C15 C14 C13 C12 0.90(15) . . . . ?
C15 C14 C13 C16 -177.22(13) . . . . ?
C15 C14 C19 C18 177.03(15) . . . . ?
C15 C20 C21 O3 21.4(3) . . . . ?
C15 C20 C21 C22 -164.16(14) . . . . ?
C1 N1 C2 C3 1.80(15) . . . . ?
C1 N1 C2 C5 -178.16(14) . . . . ?
C1 C4 C10 N2 178.47(11) . . . . ?
C11 C15 C14 C13 -0.41(15) . . . . ?
C11 C15 C14 C19 -178.07(16) . . . . ?
C11 C15 C20 C24 12.3(2) . . . . ?
C11 C15 C20 C21 -177.25(14) . . . . ?
C11 C4 C10 N2 -62.04(15) . . . . ?
C24 N2 C10 C4 74.96(16) . . . . ?
C24 C23 C22 C21 -0.53(16) . . . . ?
C24 C23 C22 C25 175.41(14) . . . . ?
C24 C23 C28 C27 -174.61(15) . . . . ?
C24 C20 C21 O3 -166.73(18) . . . . ?
C24 C20 C21 C22 7.74(16) . . . . ?
C2 N1 C1 O1 177.60(14) . . . . ?
C2 N1 C1 C4 -5.20(15) . . . . ?
C2 C3 C4 C1 -5.08(13) . . . . ?
C2 C3 C4 C11 -122.78(13) . . . . ?
C2 C3 C4 C10 106.97(13) . . . . ?
C2 C3 C8 C7 -1.39(19) . . . . ?
C2 C5 C6 C7 -0.8(2) . . . . ?
C23 C24 C20 C15 164.03(13) . . . . ?
C23 C24 C20 C21 -8.28(16) . . . . ?
C23 C22 C21 O3 170.46(16) . . . . ?
C23 C22 C21 C20 -4.46(17) . . . . ?
C23 C22 C25 C26 0.1(2) . . . . ?
C23 C28 C27 C26 1.1(2) . . . . ?
C22 C23 C28 C27 -0.9(2) . . . . ?
C22 C25 C26 C27 0.0(2) . . . . ?
C14 C15 C11 C4 -179.84(13) . . . . ?
C14 C15 C11 C12 -0.26(15) . . . . ?
C14 C15 C20 C24 -159.80(13) . . . . ?
C14 C15 C20 C21 10.7(2) . . . . ?
C14 C13 C12 O2 179.34(14) . . . . ?
C14 C13 C12 C11 -1.05(15) . . . . ?
C14 C13 C16 C17 -0.7(2) . . . . ?
C14 C19 C18 C17 -0.1(3) . . . . ?
C4 C3 C2 N1 2.46(14) . . . . ?
C4 C3 C2 C5 -177.58(12) . . . . ?
C4 C3 C8 C7 177.33(13) . . . . ?
C4 C11 C12 O2 0.1(2) . . . . ?
C4 C11 C12 C13 -179.55(11) . . . . ?
C8 C3 C2 N1 -178.56(12) . . . . ?
C8 C3 C2 C5 1.4(2) . . . . ?
C8 C3 C4 C1 176.09(14) . . . . ?
C8 C3 C4 C11 58.39(19) . . . . ?
C8 C3 C4 C10 -71.85(18) . . . . ?
C8 C7 C6 C5 0.7(2) . . . . ?
C20 C15 C11 C4 6.9(2) . . . . ?
C20 C15 C11 C12 -173.50(13) . . . . ?
C20 C15 C14 C13 173.04(13) . . . . ?
C20 C15 C14 C19 -4.6(2) . . . . ?
C20 C24 C23 C22 5.70(16) . . . . ?
C20 C24 C23 C28 -179.95(15) . . . . ?
C13 C14 C19 C18 -0.4(2) . . . . ?
C13 C16 C17 C18 0.2(2) . . . . ?
C12 C11 C4 C3 66.95(16) . . . . ?
C12 C11 C4 C1 -46.04(15) . . . . ?
C12 C11 C4 C10 -163.56(12) . . . . ?
C12 C13 C16 C17 -178.42(14) . . . . ?
C10 N2 C24 C23 150.72(13) . . . . ?
C10 N2 C24 C20 -25.3(2) . . . . ?
C21 C22 C25 C26 175.12(15) . . . . ?
C28 C23 C22 C21 -175.60(14) . . . . ?
C28 C23 C22 C25 0.3(2) . . . . ?
C28 C27 C26 C25 -0.6(3) . . . . ?
C16 C13 C12 O2 -2.7(3) . . . . ?
C16 C13 C12 C11 176.92(14) . . . . ?
C16 C17 C18 C19 0.2(3) . . . . ?
C25 C22 C21 O3 -5.0(3) . . . . ?
C25 C22 C21 C20 -179.95(15) . . . . ?
C19 C14 C13 C12 178.96(13) . . . . ?
C19 C14 C13 C16 0.8(2) . . . . ?
C9 N1 C1 O1 10.7(2) . . . . ?
C9 N1 C1 C4 -172.09(13) . . . . ?
C9 N1 C2 C3 168.34(14) . . . . ?
C9 N1 C2 C5 -11.6(2) . . . . ?

_smtbx_masks_special_details     
;
A solvent mask was calculated and 68 electrons were 
found in a volume of 310Å³ in 1 void per unit cell. 
This is consistent with the presence of 
0.5[C3H6O] per Asymmetric Unit 
which account for 64 electrons 
per unit cell.
;
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 0.000 0.500 0.000 155.1 34.5 '1 C3H6O'
2 0.500 0.000 0.500 155.1 34.5 '1 C3H6O'

_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_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 1.433
_oxdiff_exptl_absorpt_empirical_full_min 0.382
####################################################################### 
# 
# 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_swg24jc02
_database_code_depnum_ccdc_archive 'CCDC 2390187'
loop_
_audit_author_name
_audit_author_address
'Jack Clegg'
;The University of Queensalnd
Australia
;
_audit_update_record             
;
2024-10-11 deposited with the CCDC.	2024-11-27 downloaded from the CCDC.
;
_audit_creation_date             2024-10-11
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.01.12 svn.r2f8d729c for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C26 H13 N3 O5, 1[C3H6O]'
_chemical_formula_sum            'C29 H19 N3 O6'
_chemical_formula_weight         505.47
_chemical_melting_point          ?
_chemical_oxdiff_formula         C27H25N3O5
_chemical_oxdiff_usercomment     MeIsatin
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   9.8568(8)
_cell_length_b                   20.5209(17)
_cell_length_c                   11.6657(7)
_cell_angle_alpha                90
_cell_angle_beta                 107.853(8)
_cell_angle_gamma                90
_cell_volume                     2246.0(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4725
_cell_measurement_temperature    150
_cell_measurement_theta_max      32.6210
_cell_measurement_theta_min      3.0520
_shelx_estimated_absorpt_T_max   0.995
_shelx_estimated_absorpt_T_min   0.989
_exptl_absorpt_coefficient_mu    0.107
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.99137
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.128a (Rigaku Oxford Diffraction, 2024)
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    1.495
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1048
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0619
_diffrn_reflns_av_unetI/netI     0.0469
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            25280
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.122
_diffrn_reflns_theta_max         25.122
_diffrn_reflns_theta_min         1.985
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_detector_type            'Pilatus 300K'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -29.00  11.00   0.50   20.00    --    8.20 101.00 176.00   80
  2  ω    -27.00   0.00   0.50   20.00    --   -9.45 101.00 176.00   54
  3  ω      0.00  44.00   0.50   20.00    --    8.20 -99.00-180.00   88
  4  ω    -11.00  28.00   0.50   20.00    --    8.20  57.00   0.00   78
  5  ω     -2.00  45.00   0.50   20.00    --    8.20 -99.00  30.00   94
  6  ω     18.00  44.00   0.50   20.00    --    8.20 -99.00-120.00   52
  7  ω     38.00  82.00   0.50   20.00    --    8.20  57.00   0.00   88
  8  ω     -1.00  34.00   0.50   20.00    --    8.20 -99.00 120.00   70
  9  ω      0.00  36.00   0.50   20.00    --    8.20 -99.00-150.00   72
 10  ω    -29.00   6.00   0.50   20.00    --   -9.45 -37.00-150.00   70
 11  ω    -88.00 -34.00   0.50   20.00    --   -9.45 -37.00-150.00  108
 12  ω     32.00  57.00   0.50   20.00    --   -9.45  57.00 -90.00   50
 13  ω    -23.00   2.00   0.50   20.00    --   -9.45  57.00 -90.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, Pilatus 300K'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0575297000
_diffrn_orient_matrix_UB_12      -0.0186016000
_diffrn_orient_matrix_UB_13      0.0071783000
_diffrn_orient_matrix_UB_21      -0.0458232000
_diffrn_orient_matrix_UB_22      0.0272505000
_diffrn_orient_matrix_UB_23      -0.0181308000
_diffrn_orient_matrix_UB_31      -0.0174631000
_diffrn_orient_matrix_UB_32      -0.0103103000
_diffrn_orient_matrix_UB_33      -0.0608316000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3034
_reflns_number_total             4003
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _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 1.171.43.128a (Rigaku OD, 2024)'
_computing_data_collection       'CrysAlisPro 1.171.43.128a (Rigaku OD, 2024)'
_computing_data_reduction        'CrysAlisPro 1.171.43.128a (Rigaku OD, 2024)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.248
_refine_diff_density_min         -0.294
_refine_diff_density_rms         0.045
_refine_ls_extinction_coef       0.0026(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     308
_refine_ls_number_reflns         4003
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0638
_refine_ls_R_factor_gt           0.0460
_refine_ls_restrained_S_all      1.036
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0523P)²+0.5892P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1075
_refine_ls_wR_factor_ref         0.1146
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N3(H3), N1(H1), C8(H8), C14(H14), C23(H23), C17(H17), C26(H26), C16(H16),
 C15(H15), C5(H5), C6(H6), C24(H24), C25(H25)
;
_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 0.34307(14) 0.52706(7) 0.21131(10) 0.0359(4) Uani 1 1 d . . . . .
O5 O 0.25244(15) 0.35451(7) 0.22676(11) 0.0393(4) Uani 1 1 d . . . . .
O4 O 0.72375(15) 0.53705(7) 0.20566(11) 0.0409(4) Uani 1 1 d . . . . .
N3 N 0.63223(16) 0.44050(8) 0.54325(12) 0.0282(4) Uani 1 1 d . . . . .
H3 H 0.666557 0.439864 0.622336 0.034 Uiso 1 1 calc R U . . .
N1 N 0.39643(17) 0.46166(8) 0.07098(12) 0.0322(4) Uani 1 1 d . . . . .
H1 H 0.340246 0.479972 0.005327 0.039 Uiso 1 1 calc R U . . .
C10 C 0.69003(19) 0.47861(9) 0.47450(15) 0.0264(4) Uani 1 1 d . . . . .
C18 C 0.51793(19) 0.40337(9) 0.48213(14) 0.0259(4) Uani 1 1 d . . . . .
C1 C 0.4087(2) 0.48226(9) 0.18448(15) 0.0282(4) Uani 1 1 d . . . . .
C11 C 0.81159(19) 0.52356(9) 0.52144(15) 0.0282(4) Uani 1 1 d . . . . .
O3 O 0.7629(2) 0.21530(10) 0.05032(17) 0.0782(6) Uani 1 1 d . . . . .
C22 C 0.4408(2) 0.35717(9) 0.53662(15) 0.0290(4) Uani 1 1 d . . . . .
C20 C 0.3367(2) 0.36136(9) 0.32727(15) 0.0293(4) Uani 1 1 d . . . . .
C3 C 0.56126(19) 0.39224(9) 0.18876(14) 0.0278(4) Uani 1 1 d . . . . .
C4 C 0.52191(19) 0.43911(9) 0.27430(14) 0.0273(4) Uani 1 1 d . . . . .
C9 C 0.64370(19) 0.47922(9) 0.35194(15) 0.0278(4) Uani 1 1 d . . . . .
C19 C 0.4611(2) 0.40355(9) 0.36045(15) 0.0277(4) Uani 1 1 d . . . . .
C21 C 0.3304(2) 0.33036(9) 0.44177(16) 0.0306(4) Uani 1 1 d . . . . .
C12 C 0.8368(2) 0.55268(10) 0.42130(16) 0.0309(4) Uani 1 1 d . . . . .
C2 C 0.4834(2) 0.40807(10) 0.07093(15) 0.0316(5) Uani 1 1 d . . . . .
C13 C 0.7326(2) 0.52469(10) 0.31041(15) 0.0302(4) Uani 1 1 d . . . . .
N2 N 0.7566(2) 0.24797(10) 0.13638(18) 0.0574(6) Uani 1 1 d . . . . .
C8 C 0.6498(2) 0.33927(10) 0.21241(16) 0.0338(5) Uani 1 1 d . . . . .
H8 H 0.700770 0.327044 0.292610 0.041 Uiso 1 1 calc R U . . .
C14 C 0.8930(2) 0.53891(10) 0.63640(16) 0.0327(5) Uani 1 1 d . . . . .
H14 H 0.876763 0.518780 0.704340 0.039 Uiso 1 1 calc R U . . .
C23 C 0.4606(2) 0.33803(10) 0.65346(16) 0.0353(5) Uani 1 1 d . . . . .
H23 H 0.534614 0.356011 0.718294 0.042 Uiso 1 1 calc R U . . .
C17 C 0.9420(2) 0.59804(10) 0.43478(18) 0.0385(5) Uani 1 1 d . . . . .
H17 H 0.958668 0.617814 0.366703 0.046 Uiso 1 1 calc R U . . .
C7 C 0.6620(2) 0.30413(10) 0.11446(17) 0.0380(5) Uani 1 1 d . . . . .
C26 C 0.2400(2) 0.28440(10) 0.46165(18) 0.0390(5) Uani 1 1 d . . . . .
H26 H 0.165750 0.266452 0.396941 0.047 Uiso 1 1 calc R U . . .
C16 C 1.0241(2) 0.61448(11) 0.55139(19) 0.0423(5) Uani 1 1 d . . . . .
H16 H 1.097112 0.646294 0.563009 0.051 Uiso 1 1 calc R U . . .
O2 O 0.8244(3) 0.23495(11) 0.24014(17) 0.0998(8) Uani 1 1 d . . . . .
C15 C 1.0008(2) 0.58520(11) 0.65002(18) 0.0403(5) Uani 1 1 d . . . . .
H15 H 1.059012 0.596686 0.728602 0.048 Uiso 1 1 calc R U . . .
C5 C 0.4953(2) 0.37210(11) -0.02560(17) 0.0424(5) Uani 1 1 d . . . . .
H5 H 0.442117 0.383285 -0.105810 0.051 Uiso 1 1 calc R U . . .
C6 C 0.5864(3) 0.31970(11) -0.00223(17) 0.0453(6) Uani 1 1 d . . . . .
H6 H 0.597168 0.294172 -0.066834 0.054 Uiso 1 1 calc R U . . .
C24 C 0.3675(2) 0.29109(11) 0.67322(18) 0.0440(5) Uani 1 1 d . . . . .
H24 H 0.378557 0.277072 0.753183 0.053 Uiso 1 1 calc R U . . .
C25 C 0.2604(2) 0.26471(11) 0.58001(19) 0.0465(6) Uani 1 1 d . . . . .
H25 H 0.199379 0.232617 0.596467 0.056 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.219(2) . ?
O5 C20 1.220(2) . ?
O4 C13 1.225(2) . ?
N3 H3 0.8800 . ?
N3 C10 1.364(2) . ?
N3 C18 1.366(2) . ?
N1 H1 0.8800 . ?
N1 C1 1.359(2) . ?
N1 C2 1.395(3) . ?
C10 C11 1.478(3) . ?
C10 C9 1.361(2) . ?
C18 C22 1.476(3) . ?
C18 C19 1.357(2) . ?
C1 C4 1.552(3) . ?
C11 C12 1.401(3) . ?
C11 C14 1.372(2) . ?
O3 N2 1.225(2) . ?
C22 C21 1.405(3) . ?
C22 C23 1.374(2) . ?
C20 C19 1.453(3) . ?
C20 C21 1.498(2) . ?
C3 C4 1.519(2) . ?
C3 C2 1.392(2) . ?
C3 C8 1.368(3) . ?
C4 C9 1.507(3) . ?
C4 C19 1.507(2) . ?
C9 C13 1.461(3) . ?
C21 C26 1.365(3) . ?
C12 C13 1.498(3) . ?
C12 C17 1.366(3) . ?
C2 C5 1.381(3) . ?
N2 C7 1.455(3) . ?
N2 O2 1.220(2) . ?
C8 H8 0.9500 . ?
C8 C7 1.387(3) . ?
C14 H14 0.9500 . ?
C14 C15 1.397(3) . ?
C23 H23 0.9500 . ?
C23 C24 1.397(3) . ?
C17 H17 0.9500 . ?
C17 C16 1.394(3) . ?
C7 C6 1.374(3) . ?
C26 H26 0.9500 . ?
C26 C25 1.393(3) . ?
C16 H16 0.9500 . ?
C16 C15 1.378(3) . ?
C15 H15 0.9500 . ?
C5 H5 0.9500 . ?
C5 C6 1.374(3) . ?
C6 H6 0.9500 . ?
C24 H24 0.9500 . ?
C24 C25 1.373(3) . ?
C25 H25 0.9500 . ?

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
C10 N3 H3 122.0 . . ?
C10 N3 C18 116.06(14) . . ?
C18 N3 H3 122.0 . . ?
C1 N1 H1 124.0 . . ?
C1 N1 C2 111.98(15) . . ?
C2 N1 H1 124.0 . . ?
N3 C10 C11 125.27(15) . . ?
C9 C10 N3 123.85(17) . . ?
C9 C10 C11 110.87(16) . . ?
N3 C18 C22 125.80(15) . . ?
C19 C18 N3 123.67(16) . . ?
C19 C18 C22 110.52(16) . . ?
O1 C1 N1 126.06(17) . . ?
O1 C1 C4 125.81(15) . . ?
N1 C1 C4 108.13(16) . . ?
C12 C11 C10 106.75(15) . . ?
C14 C11 C10 132.11(17) . . ?
C14 C11 C12 121.14(18) . . ?
C21 C22 C18 106.82(15) . . ?
C23 C22 C18 132.54(18) . . ?
C23 C22 C21 120.63(18) . . ?
O5 C20 C19 126.52(17) . . ?
O5 C20 C21 127.32(18) . . ?
C19 C20 C21 106.13(15) . . ?
C2 C3 C4 109.05(16) . . ?
C8 C3 C4 130.24(16) . . ?
C8 C3 C2 120.61(17) . . ?
C3 C4 C1 101.13(13) . . ?
C9 C4 C1 111.67(15) . . ?
C9 C4 C3 115.07(15) . . ?
C19 C4 C1 112.08(15) . . ?
C19 C4 C3 111.42(15) . . ?
C19 C4 C9 105.66(13) . . ?
C10 C9 C4 125.10(16) . . ?
C10 C9 C13 108.19(16) . . ?
C13 C9 C4 126.71(15) . . ?
C18 C19 C20 108.72(16) . . ?
C18 C19 C4 125.31(17) . . ?
C20 C19 C4 125.90(15) . . ?
C22 C21 C20 107.59(16) . . ?
C26 C21 C22 121.68(17) . . ?
C26 C21 C20 130.74(18) . . ?
C11 C12 C13 107.87(17) . . ?
C17 C12 C11 121.14(17) . . ?
C17 C12 C13 130.99(17) . . ?
C3 C2 N1 109.67(15) . . ?
C5 C2 N1 128.88(17) . . ?
C5 C2 C3 121.43(19) . . ?
O4 C13 C9 126.64(17) . . ?
O4 C13 C12 127.06(18) . . ?
C9 C13 C12 106.30(15) . . ?
O3 N2 C7 118.7(2) . . ?
O2 N2 O3 122.9(2) . . ?
O2 N2 C7 118.33(18) . . ?
C3 C8 H8 121.4 . . ?
C3 C8 C7 117.26(17) . . ?
C7 C8 H8 121.4 . . ?
C11 C14 H14 121.2 . . ?
C11 C14 C15 117.64(18) . . ?
C15 C14 H14 121.2 . . ?
C22 C23 H23 121.3 . . ?
C22 C23 C24 117.40(19) . . ?
C24 C23 H23 121.3 . . ?
C12 C17 H17 121.0 . . ?
C12 C17 C16 118.05(18) . . ?
C16 C17 H17 121.0 . . ?
C8 C7 N2 118.68(18) . . ?
C6 C7 N2 118.82(18) . . ?
C6 C7 C8 122.50(19) . . ?
C21 C26 H26 121.1 . . ?
C21 C26 C25 117.76(19) . . ?
C25 C26 H26 121.1 . . ?
C17 C16 H16 119.6 . . ?
C15 C16 C17 120.9(2) . . ?
C15 C16 H16 119.6 . . ?
C14 C15 H15 119.4 . . ?
C16 C15 C14 121.12(18) . . ?
C16 C15 H15 119.4 . . ?
C2 C5 H5 121.0 . . ?
C6 C5 C2 118.06(18) . . ?
C6 C5 H5 121.0 . . ?
C7 C6 H6 119.9 . . ?
C5 C6 C7 120.11(18) . . ?
C5 C6 H6 119.9 . . ?
C23 C24 H24 119.1 . . ?
C25 C24 C23 121.70(18) . . ?
C25 C24 H24 119.1 . . ?
C26 C25 H25 119.6 . . ?
C24 C25 C26 120.8(2) . . ?
C24 C25 H25 119.6 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C4 C3 178.68(18) . . . . ?
O1 C1 C4 C9 -58.4(2) . . . . ?
O1 C1 C4 C19 59.9(2) . . . . ?
O5 C20 C19 C18 173.02(18) . . . . ?
O5 C20 C19 C4 -9.8(3) . . . . ?
O5 C20 C21 C22 -174.12(19) . . . . ?
O5 C20 C21 C26 5.9(3) . . . . ?
N3 C10 C11 C12 179.75(17) . . . . ?
N3 C10 C11 C14 -0.5(3) . . . . ?
N3 C10 C9 C4 0.8(3) . . . . ?
N3 C10 C9 C13 -178.84(17) . . . . ?
N3 C18 C22 C21 179.28(17) . . . . ?
N3 C18 C22 C23 -1.8(3) . . . . ?
N3 C18 C19 C20 -176.82(17) . . . . ?
N3 C18 C19 C4 6.0(3) . . . . ?
N1 C1 C4 C3 -1.72(19) . . . . ?
N1 C1 C4 C9 121.16(16) . . . . ?
N1 C1 C4 C19 -120.51(16) . . . . ?
N1 C2 C5 C6 -178.1(2) . . . . ?
C10 N3 C18 C22 178.12(17) . . . . ?
C10 N3 C18 C19 -0.7(3) . . . . ?
C10 C11 C12 C13 -1.3(2) . . . . ?
C10 C11 C12 C17 178.83(18) . . . . ?
C10 C11 C14 C15 -178.96(18) . . . . ?
C10 C9 C13 O4 178.68(18) . . . . ?
C10 C9 C13 C12 -1.0(2) . . . . ?
C18 N3 C10 C11 178.57(16) . . . . ?
C18 N3 C10 C9 -2.6(3) . . . . ?
C18 C22 C21 C20 -1.3(2) . . . . ?
C18 C22 C21 C26 178.64(18) . . . . ?
C18 C22 C23 C24 -178.5(2) . . . . ?
C1 N1 C2 C3 -1.6(2) . . . . ?
C1 N1 C2 C5 176.9(2) . . . . ?
C1 C4 C9 C10 125.57(19) . . . . ?
C1 C4 C9 C13 -54.8(2) . . . . ?
C1 C4 C19 C18 -128.53(19) . . . . ?
C1 C4 C19 C20 54.7(2) . . . . ?
C11 C10 C9 C4 179.81(17) . . . . ?
C11 C10 C9 C13 0.2(2) . . . . ?
C11 C12 C13 O4 -178.21(19) . . . . ?
C11 C12 C13 C9 1.4(2) . . . . ?
C11 C12 C17 C16 0.2(3) . . . . ?
C11 C14 C15 C16 0.2(3) . . . . ?
O3 N2 C7 C8 177.0(2) . . . . ?
O3 N2 C7 C6 -1.9(3) . . . . ?
C22 C18 C19 C20 4.2(2) . . . . ?
C22 C18 C19 C4 -173.03(17) . . . . ?
C22 C21 C26 C25 0.1(3) . . . . ?
C22 C23 C24 C25 0.2(3) . . . . ?
C20 C21 C26 C25 -179.9(2) . . . . ?
C3 C4 C9 C10 -119.90(19) . . . . ?
C3 C4 C9 C13 59.7(2) . . . . ?
C3 C4 C19 C18 118.95(19) . . . . ?
C3 C4 C19 C20 -57.8(2) . . . . ?
C3 C2 C5 C6 0.2(3) . . . . ?
C3 C8 C7 N2 179.28(18) . . . . ?
C3 C8 C7 C6 -1.9(3) . . . . ?
C4 C3 C2 N1 0.4(2) . . . . ?
C4 C3 C2 C5 -178.25(18) . . . . ?
C4 C3 C8 C7 178.20(19) . . . . ?
C4 C9 C13 O4 -1.0(3) . . . . ?
C4 C9 C13 C12 179.40(17) . . . . ?
C9 C10 C11 C12 0.8(2) . . . . ?
C9 C10 C11 C14 -179.5(2) . . . . ?
C9 C4 C19 C18 -6.7(2) . . . . ?
C9 C4 C19 C20 176.55(17) . . . . ?
C19 C18 C22 C21 -1.8(2) . . . . ?
C19 C18 C22 C23 177.2(2) . . . . ?
C19 C20 C21 C22 3.7(2) . . . . ?
C19 C20 C21 C26 -176.2(2) . . . . ?
C19 C4 C9 C10 3.5(2) . . . . ?
C19 C4 C9 C13 -176.95(17) . . . . ?
C21 C22 C23 C24 0.3(3) . . . . ?
C21 C20 C19 C18 -4.9(2) . . . . ?
C21 C20 C19 C4 172.33(17) . . . . ?
C21 C26 C25 C24 0.3(3) . . . . ?
C12 C11 C14 C15 0.8(3) . . . . ?
C12 C17 C16 C15 0.8(3) . . . . ?
C2 N1 C1 O1 -178.30(18) . . . . ?
C2 N1 C1 C4 2.1(2) . . . . ?
C2 C3 C4 C1 0.80(19) . . . . ?
C2 C3 C4 C9 -119.70(17) . . . . ?
C2 C3 C4 C19 120.06(17) . . . . ?
C2 C3 C8 C7 2.4(3) . . . . ?
C2 C5 C6 C7 0.3(3) . . . . ?
C13 C12 C17 C16 -179.63(19) . . . . ?
N2 C7 C6 C5 179.4(2) . . . . ?
C8 C3 C4 C1 -175.42(19) . . . . ?
C8 C3 C4 C9 64.1(3) . . . . ?
C8 C3 C4 C19 -56.2(3) . . . . ?
C8 C3 C2 N1 177.00(17) . . . . ?
C8 C3 C2 C5 -1.6(3) . . . . ?
C8 C7 C6 C5 0.6(3) . . . . ?
C14 C11 C12 C13 178.88(17) . . . . ?
C14 C11 C12 C17 -1.0(3) . . . . ?
C23 C22 C21 C20 179.57(17) . . . . ?
C23 C22 C21 C26 -0.5(3) . . . . ?
C23 C24 C25 C26 -0.5(4) . . . . ?
C17 C12 C13 O4 1.6(4) . . . . ?
C17 C12 C13 C9 -178.7(2) . . . . ?
C17 C16 C15 C14 -0.9(3) . . . . ?
O2 N2 C7 C8 -1.9(3) . . . . ?
O2 N2 C7 C6 179.3(2) . . . . ?

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 0.000 0.000 0.500 211.1 52.8 '2 C3H6O'
2 0.000 0.500 0.000 211.1 52.8 '2 C3H6O'

_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_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 1.089
_oxdiff_exptl_absorpt_empirical_full_min 0.913
