# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2024

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

data_ag2018
_database_code_depnum_ccdc_archive 'CCDC 2263627'
loop_
_audit_author_name
_audit_author_address
'Michel Giorgi'
;University of Aix Marseille
France
;
_audit_update_record             
;
2023-05-17 deposited with the CCDC.	2024-04-19 downloaded from the CCDC.
;
_audit_creation_date             2021-09-10
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C28 H21 N O4'
_chemical_formula_sum            'C28 H21 N O4'
_chemical_formula_weight         435.46
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         'c28 h21 n1 o4'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   12.28419(14)
_cell_length_b                   13.47791(17)
_cell_length_c                   13.83030(17)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2289.82(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9461
_cell_measurement_temperature    295
_cell_measurement_theta_max      72.8220
_cell_measurement_theta_min      3.1370
_shelx_estimated_absorpt_T_max   0.947
_shelx_estimated_absorpt_T_min   0.864
_exptl_absorpt_coefficient_mu    0.685
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.76110
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.116a (Rigaku Oxford Diffraction, 2021)
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    1.263
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             912
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0331
_diffrn_reflns_av_unetI/netI     0.0218
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            17009
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.917
_diffrn_reflns_theta_min         4.581
_diffrn_ambient_temperature      295
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3048
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -71.00  32.00   1.00    1.50    --  -40.79  65.00 -12.00  103
  2  ω     27.00 140.00   1.00   12.50    --  105.59 -83.00 100.00  113
  3  ω     74.00 178.00   1.00   12.50    --  105.59  73.00 112.00  104
  4  ω     23.00  97.00   1.00    1.50    --   40.79-125.00-120.00   74
  5  ω     23.00  97.00   1.00    1.50    --   40.79-125.00 120.00   74
  6  ω     23.00  97.00   1.00    1.50    --   40.79-125.00-150.00   74
  7  ω     80.00 178.00   1.00   12.50    --  105.59  45.00-180.00   98
  8  ω     32.00 118.00   1.00   12.50    --  105.59-125.00-150.00   86
  9  ω     80.00 178.00   1.00   12.50    --  105.59  45.00 -90.00   98
 10  ω     94.00 178.00   1.00   12.50    --  105.59 125.00 -60.00   84
 11  ω     33.00 135.00   1.00   12.50    --  105.59 -65.00-148.00  102
 12  ω   -113.00 -13.00   1.00    1.50    --  -40.79 -57.00-120.00  100
 13  ω   -117.00 -26.00   1.00    1.50    --  -40.79 -77.00 120.00   91
 14  ω   -113.00 -13.00   1.00    1.50    --  -40.79 -57.00   0.00  100
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1056739000
_diffrn_orient_matrix_UB_12      -0.0599867000
_diffrn_orient_matrix_UB_13      0.0138252000
_diffrn_orient_matrix_UB_21      -0.0353503000
_diffrn_orient_matrix_UB_22      -0.0714525000
_diffrn_orient_matrix_UB_23      -0.0811630000
_diffrn_orient_matrix_UB_31      0.0576519000
_diffrn_orient_matrix_UB_32      0.0661336000
_diffrn_orient_matrix_UB_33      -0.0750913000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.751
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.968
_reflns_number_gt                4184
_reflns_number_total             4475
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.116a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.116a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.116a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.127
_refine_diff_density_min         -0.155
_refine_diff_density_rms         0.032
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.0(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     300
_refine_ls_number_reflns         4475
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0400
_refine_ls_R_factor_gt           0.0371
_refine_ls_restrained_S_all      1.025
_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)+(0.0641P)²+0.1170P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0992
_refine_ls_wR_factor_ref         0.1032
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 1.0(3)
 0.0(3)
2. 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
3.a Ternary CH refined with riding coordinates:
 C1(H1), C2(H2)
3.b Secondary CH2 refined with riding coordinates:
 C21(H21A,H21B)
3.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C7(H7), C8(H8), C16(H16), C17(H17), C18(H18), C19(H19),
 C20(H20), C24(H24), C25(H25), C26(H26), C27(H27), C28(H28)
3.d Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.12562(14) 0.32951(15) 0.16338(13) 0.0695(5) Uani 1 1 d . . . . .
O2 O 0.54031(12) 0.45466(13) 0.50200(11) 0.0600(4) Uani 1 1 d . . . . .
O3 O -0.02860(18) 0.4315(2) 0.2439(2) 0.1198(10) Uani 1 1 d . . . . .
O4 O 0.0497(2) 0.5717(2) 0.21792(19) 0.1018(8) Uani 1 1 d . . . . .
N1 N 0.04385(18) 0.4820(2) 0.21149(16) 0.0784(7) Uani 1 1 d . . . . .
C1 C 0.24662(16) 0.45919(15) 0.20482(14) 0.0479(4) Uani 1 1 d . . . . .
H1 H 0.240417 0.522927 0.238475 0.057 Uiso 1 1 calc R U . . .
C2 C 0.13843(17) 0.43128(19) 0.15599(17) 0.0602(6) Uani 1 1 d . . . . .
H2 H 0.138539 0.451832 0.088015 0.072 Uiso 1 1 calc R U . . .
C3 C 0.18465(18) 0.30152(18) 0.24449(17) 0.0577(5) Uani 1 1 d . . . . .
C4 C 0.1741(2) 0.2083(2) 0.2862(2) 0.0725(7) Uani 1 1 d . . . . .
H4 H 0.125438 0.161526 0.262225 0.087 Uiso 1 1 calc R U . . .
C5 C 0.2383(2) 0.18907(18) 0.3633(2) 0.0692(6) Uani 1 1 d . . . . .
H5 H 0.233519 0.127131 0.392662 0.083 Uiso 1 1 calc R U . . .
C6 C 0.31271(19) 0.25964(16) 0.40142(18) 0.0555(5) Uani 1 1 d . . . . .
C7 C 0.3798(2) 0.23180(18) 0.4802(2) 0.0675(6) Uani 1 1 d . . . . .
H7 H 0.369941 0.169785 0.508348 0.081 Uiso 1 1 calc R U . . .
C8 C 0.4579(2) 0.29271(19) 0.51578(19) 0.0678(6) Uani 1 1 d . . . . .
H8 H 0.503761 0.273346 0.565838 0.081 Uiso 1 1 calc R U . . .
C9 C 0.46545(17) 0.38597(16) 0.47301(15) 0.0515(4) Uani 1 1 d . . . . .
C10 C 0.51850(18) 0.53878(17) 0.44981(16) 0.0542(5) Uani 1 1 d . . . . .
C11 C 0.43272(15) 0.52583(15) 0.38896(13) 0.0442(4) Uani 1 1 d . . . . .
C12 C 0.39876(15) 0.42289(14) 0.40096(13) 0.0427(4) Uani 1 1 d . . . . .
C13 C 0.32092(15) 0.35647(14) 0.35805(14) 0.0440(4) Uani 1 1 d . . . . .
C14 C 0.25410(16) 0.37439(15) 0.27638(14) 0.0463(4) Uani 1 1 d . . . . .
C15 C 0.33711(15) 0.46247(15) 0.12958(14) 0.0458(4) Uani 1 1 d . . . . .
C16 C 0.4206(2) 0.39411(18) 0.1277(2) 0.0625(6) Uani 1 1 d . . . . .
H16 H 0.423858 0.344797 0.174633 0.075 Uiso 1 1 calc R U . . .
C17 C 0.4999(2) 0.3983(2) 0.0563(2) 0.0795(8) Uani 1 1 d . . . . .
H17 H 0.556396 0.352391 0.056330 0.095 Uiso 1 1 calc R U . . .
C18 C 0.4955(2) 0.4699(2) -0.0144(2) 0.0733(7) Uani 1 1 d . . . . .
H18 H 0.547507 0.471396 -0.063264 0.088 Uiso 1 1 calc R U . . .
C19 C 0.4136(2) 0.5392(2) -0.01238(18) 0.0653(6) Uani 1 1 d . . . . .
H19 H 0.410863 0.588521 -0.059358 0.078 Uiso 1 1 calc R U . . .
C20 C 0.33522(19) 0.53605(17) 0.05906(16) 0.0558(5) Uani 1 1 d . . . . .
H20 H 0.280484 0.583710 0.060074 0.067 Uiso 1 1 calc R U . . .
C21 C 0.5893(2) 0.6252(2) 0.4727(2) 0.0750(7) Uani 1 1 d . . . . .
H21A H 0.561790 0.683035 0.438797 0.090 Uiso 1 1 calc R U . . .
H21B H 0.584907 0.638718 0.541453 0.090 Uiso 1 1 calc R U . . .
C22 C 0.7053(3) 0.6105(4) 0.4460(4) 0.1186(14) Uani 1 1 d . . . . .
H22A H 0.739587 0.568212 0.492842 0.178 Uiso 1 1 calc R U . . .
H22B H 0.741683 0.673514 0.444736 0.178 Uiso 1 1 calc R U . . .
H22C H 0.709531 0.580257 0.383307 0.178 Uiso 1 1 calc R U . . .
C23 C 0.38271(17) 0.60970(14) 0.33626(14) 0.0472(4) Uani 1 1 d . . . . .
C24 C 0.4352(2) 0.65769(18) 0.26108(17) 0.0639(6) Uani 1 1 d . . . . .
H24 H 0.502973 0.635341 0.240478 0.077 Uiso 1 1 calc R U . . .
C25 C 0.3879(4) 0.7384(2) 0.2165(2) 0.0878(10) Uani 1 1 d . . . . .
H25 H 0.424235 0.770309 0.166380 0.105 Uiso 1 1 calc R U . . .
C26 C 0.2870(4) 0.7721(2) 0.2456(3) 0.0918(11) Uani 1 1 d . . . . .
H26 H 0.255105 0.826079 0.214787 0.110 Uiso 1 1 calc R U . . .
C27 C 0.2334(3) 0.7251(2) 0.3208(2) 0.0783(8) Uani 1 1 d . . . . .
H27 H 0.165290 0.747333 0.340529 0.094 Uiso 1 1 calc R U . . .
C28 C 0.2815(2) 0.64525(17) 0.36632(17) 0.0584(5) Uani 1 1 d . . . . .
H28 H 0.245970 0.614716 0.417718 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 C2 1.384(3) . ?
O1 C3 1.388(3) . ?
O2 C9 1.365(3) . ?
O2 C10 1.370(3) . ?
O3 N1 1.207(4) . ?
O4 N1 1.213(4) . ?
N1 C2 1.552(3) . ?
C1 H1 0.9800 . ?
C1 C2 1.538(3) . ?
C1 C14 1.515(3) . ?
C1 C15 1.523(3) . ?
C2 H2 0.9800 . ?
C3 C4 1.388(4) . ?
C3 C14 1.374(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.352(4) . ?
C5 H5 0.9300 . ?
C5 C6 1.421(4) . ?
C6 C7 1.417(4) . ?
C6 C13 1.440(3) . ?
C7 H7 0.9300 . ?
C7 C8 1.355(4) . ?
C8 H8 0.9300 . ?
C8 C9 1.392(3) . ?
C9 C12 1.383(3) . ?
C10 C11 1.360(3) . ?
C10 C21 1.488(3) . ?
C11 C12 1.458(3) . ?
C11 C23 1.479(3) . ?
C12 C13 1.438(3) . ?
C13 C14 1.417(3) . ?
C15 C16 1.379(3) . ?
C15 C20 1.391(3) . ?
C16 H16 0.9300 . ?
C16 C17 1.388(4) . ?
C17 H17 0.9300 . ?
C17 C18 1.376(4) . ?
C18 H18 0.9300 . ?
C18 C19 1.373(4) . ?
C19 H19 0.9300 . ?
C19 C20 1.380(4) . ?
C20 H20 0.9300 . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C21 C22 1.484(5) . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 C24 1.384(3) . ?
C23 C28 1.396(3) . ?
C24 H24 0.9300 . ?
C24 C25 1.378(4) . ?
C25 H25 0.9300 . ?
C25 C26 1.380(6) . ?
C26 H26 0.9300 . ?
C26 C27 1.383(5) . ?
C27 H27 0.9300 . ?
C27 C28 1.380(4) . ?
C28 H28 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 O1 C3 105.64(17) . . ?
C9 O2 C10 105.94(15) . . ?
O3 N1 O4 125.3(3) . . ?
O3 N1 C2 119.2(3) . . ?
O4 N1 C2 115.5(3) . . ?
C2 C1 H1 110.8 . . ?
C14 C1 H1 110.8 . . ?
C14 C1 C2 98.91(17) . . ?
C14 C1 C15 115.09(16) . . ?
C15 C1 H1 110.8 . . ?
C15 C1 C2 109.74(16) . . ?
O1 C2 N1 108.4(2) . . ?
O1 C2 C1 107.95(19) . . ?
O1 C2 H2 110.6 . . ?
N1 C2 H2 110.6 . . ?
C1 C2 N1 108.79(17) . . ?
C1 C2 H2 110.6 . . ?
O1 C3 C4 122.2(2) . . ?
C14 C3 O1 112.9(2) . . ?
C14 C3 C4 124.9(2) . . ?
C3 C4 H4 121.7 . . ?
C5 C4 C3 116.6(2) . . ?
C5 C4 H4 121.7 . . ?
C4 C5 H5 118.7 . . ?
C4 C5 C6 122.6(2) . . ?
C6 C5 H5 118.7 . . ?
C5 C6 C13 119.8(2) . . ?
C7 C6 C5 118.8(2) . . ?
C7 C6 C13 121.3(2) . . ?
C6 C7 H7 119.0 . . ?
C8 C7 C6 122.0(2) . . ?
C8 C7 H7 119.0 . . ?
C7 C8 H8 122.0 . . ?
C7 C8 C9 116.1(2) . . ?
C9 C8 H8 122.0 . . ?
O2 C9 C8 122.17(19) . . ?
O2 C9 C12 111.52(18) . . ?
C12 C9 C8 126.3(2) . . ?
O2 C10 C21 114.9(2) . . ?
C11 C10 O2 111.80(18) . . ?
C11 C10 C21 133.2(2) . . ?
C10 C11 C12 105.86(18) . . ?
C10 C11 C23 121.93(18) . . ?
C12 C11 C23 131.65(17) . . ?
C9 C12 C11 104.77(17) . . ?
C9 C12 C13 117.86(18) . . ?
C13 C12 C11 137.36(18) . . ?
C12 C13 C6 116.04(18) . . ?
C14 C13 C6 116.49(19) . . ?
C14 C13 C12 127.45(17) . . ?
C3 C14 C1 106.98(18) . . ?
C3 C14 C13 119.6(2) . . ?
C13 C14 C1 133.20(18) . . ?
C16 C15 C1 122.44(19) . . ?
C16 C15 C20 118.4(2) . . ?
C20 C15 C1 119.17(18) . . ?
C15 C16 H16 119.7 . . ?
C15 C16 C17 120.5(2) . . ?
C17 C16 H16 119.7 . . ?
C16 C17 H17 119.8 . . ?
C18 C17 C16 120.5(3) . . ?
C18 C17 H17 119.8 . . ?
C17 C18 H18 120.3 . . ?
C19 C18 C17 119.4(2) . . ?
C19 C18 H18 120.3 . . ?
C18 C19 H19 119.8 . . ?
C18 C19 C20 120.3(2) . . ?
C20 C19 H19 119.8 . . ?
C15 C20 H20 119.6 . . ?
C19 C20 C15 120.8(2) . . ?
C19 C20 H20 119.6 . . ?
C10 C21 H21A 108.8 . . ?
C10 C21 H21B 108.8 . . ?
H21A C21 H21B 107.7 . . ?
C22 C21 C10 113.8(3) . . ?
C22 C21 H21A 108.8 . . ?
C22 C21 H21B 108.8 . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C24 C23 C11 122.3(2) . . ?
C24 C23 C28 118.6(2) . . ?
C28 C23 C11 119.05(18) . . ?
C23 C24 H24 119.7 . . ?
C25 C24 C23 120.5(3) . . ?
C25 C24 H24 119.7 . . ?
C24 C25 H25 119.7 . . ?
C24 C25 C26 120.5(3) . . ?
C26 C25 H25 119.7 . . ?
C25 C26 H26 120.1 . . ?
C25 C26 C27 119.7(3) . . ?
C27 C26 H26 120.1 . . ?
C26 C27 H27 120.1 . . ?
C28 C27 C26 119.8(3) . . ?
C28 C27 H27 120.1 . . ?
C23 C28 H28 119.6 . . ?
C27 C28 C23 120.8(2) . . ?
C27 C28 H28 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 C3 C4 C5 178.2(2) . . . . ?
O1 C3 C14 C1 -4.0(2) . . . . ?
O1 C3 C14 C13 -179.29(17) . . . . ?
O2 C9 C12 C11 -3.4(2) . . . . ?
O2 C9 C12 C13 175.50(16) . . . . ?
O2 C10 C11 C12 -2.0(2) . . . . ?
O2 C10 C11 C23 170.36(17) . . . . ?
O2 C10 C21 C22 66.0(4) . . . . ?
O3 N1 C2 O1 -6.3(3) . . . . ?
O3 N1 C2 C1 -123.4(3) . . . . ?
O4 N1 C2 O1 174.1(2) . . . . ?
O4 N1 C2 C1 57.0(3) . . . . ?
C1 C15 C16 C17 178.3(2) . . . . ?
C1 C15 C20 C19 -177.61(19) . . . . ?
C2 O1 C3 C4 167.1(2) . . . . ?
C2 O1 C3 C14 -14.1(2) . . . . ?
C2 C1 C14 C3 18.1(2) . . . . ?
C2 C1 C14 C13 -167.5(2) . . . . ?
C2 C1 C15 C16 -111.4(2) . . . . ?
C2 C1 C15 C20 67.6(2) . . . . ?
C3 O1 C2 N1 -91.6(2) . . . . ?
C3 O1 C2 C1 26.0(2) . . . . ?
C3 C4 C5 C6 0.4(4) . . . . ?
C4 C3 C14 C1 174.8(2) . . . . ?
C4 C3 C14 C13 -0.4(3) . . . . ?
C4 C5 C6 C7 -177.6(2) . . . . ?
C4 C5 C6 C13 0.7(4) . . . . ?
C5 C6 C7 C8 175.2(2) . . . . ?
C5 C6 C13 C12 -179.7(2) . . . . ?
C5 C6 C13 C14 -1.6(3) . . . . ?
C6 C7 C8 C9 2.6(4) . . . . ?
C6 C13 C14 C1 -172.33(19) . . . . ?
C6 C13 C14 C3 1.4(3) . . . . ?
C7 C6 C13 C12 -1.5(3) . . . . ?
C7 C6 C13 C14 176.6(2) . . . . ?
C7 C8 C9 O2 179.9(2) . . . . ?
C7 C8 C9 C12 2.5(4) . . . . ?
C8 C9 C12 C11 174.2(2) . . . . ?
C8 C9 C12 C13 -6.9(3) . . . . ?
C9 O2 C10 C11 0.0(2) . . . . ?
C9 O2 C10 C21 178.1(2) . . . . ?
C9 C12 C13 C6 6.0(3) . . . . ?
C9 C12 C13 C14 -171.91(18) . . . . ?
C10 O2 C9 C8 -175.5(2) . . . . ?
C10 O2 C9 C12 2.2(2) . . . . ?
C10 C11 C12 C9 3.2(2) . . . . ?
C10 C11 C12 C13 -175.3(2) . . . . ?
C10 C11 C23 C24 70.6(3) . . . . ?
C10 C11 C23 C28 -106.0(2) . . . . ?
C11 C10 C21 C22 -116.4(4) . . . . ?
C11 C12 C13 C6 -175.6(2) . . . . ?
C11 C12 C13 C14 6.5(3) . . . . ?
C11 C23 C24 C25 -177.2(2) . . . . ?
C11 C23 C28 C27 178.2(2) . . . . ?
C12 C11 C23 C24 -119.2(2) . . . . ?
C12 C11 C23 C28 64.1(3) . . . . ?
C12 C13 C14 C1 5.5(3) . . . . ?
C12 C13 C14 C3 179.31(19) . . . . ?
C13 C6 C7 C8 -3.0(4) . . . . ?
C14 C1 C2 O1 -27.1(2) . . . . ?
C14 C1 C2 N1 90.3(2) . . . . ?
C14 C1 C15 C16 -1.0(3) . . . . ?
C14 C1 C15 C20 178.11(17) . . . . ?
C14 C3 C4 C5 -0.5(4) . . . . ?
C15 C1 C2 O1 93.7(2) . . . . ?
C15 C1 C2 N1 -148.9(2) . . . . ?
C15 C1 C14 C3 -98.7(2) . . . . ?
C15 C1 C14 C13 75.7(3) . . . . ?
C15 C16 C17 C18 -0.9(5) . . . . ?
C16 C15 C20 C19 1.5(3) . . . . ?
C16 C17 C18 C19 1.9(5) . . . . ?
C17 C18 C19 C20 -1.1(4) . . . . ?
C18 C19 C20 C15 -0.6(3) . . . . ?
C20 C15 C16 C17 -0.8(4) . . . . ?
C21 C10 C11 C12 -179.7(3) . . . . ?
C21 C10 C11 C23 -7.3(4) . . . . ?
C23 C11 C12 C9 -168.15(19) . . . . ?
C23 C11 C12 C13 13.3(4) . . . . ?
C23 C24 C25 C26 -0.5(4) . . . . ?
C24 C23 C28 C27 1.5(3) . . . . ?
C24 C25 C26 C27 0.7(5) . . . . ?
C25 C26 C27 C28 0.3(5) . . . . ?
C26 C27 C28 C23 -1.3(4) . . . . ?
C28 C23 C24 C25 -0.5(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.265
_oxdiff_exptl_absorpt_empirical_full_min 0.812
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 1.0(3)
2 0.0(3)

####################################################################### 
# 
# 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_ag3-166
_database_code_depnum_ccdc_archive 'CCDC 2263636'
loop_
_audit_author_name
_audit_author_address
'Michel Giorgi'
;University of Aix Marseille
France
;
_audit_update_record             
;
2023-05-17 deposited with the CCDC.	2024-04-19 downloaded from the CCDC.
;
_audit_creation_date             2023-03-24
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C27 H19 N O5)'
_chemical_formula_sum            'C54 H38 N2 O10'
_chemical_formula_weight         874.86
_chemical_absolute_configuration unk
_chemical_melting_point          ?
_chemical_oxdiff_formula         'c27 h19 n1 o5'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, z+1/2'

_cell_length_a                   15.4716(8)
_cell_length_b                   10.1507(8)
_cell_length_c                   27.2357(19)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4277.3(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7753
_cell_measurement_temperature    295
_cell_measurement_theta_max      75.9970
_cell_measurement_theta_min      4.7020
_shelx_estimated_absorpt_T_max   0.970
_shelx_estimated_absorpt_T_min   0.801
_exptl_absorpt_coefficient_mu    0.773
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.76966
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.84a (Rigaku Oxford Diffraction, 2023)
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    1.359
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1824
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.04
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0482
_diffrn_reflns_av_unetI/netI     0.0405
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.964
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            29242
_diffrn_reflns_point_group_measured_fraction_full 0.892
_diffrn_reflns_point_group_measured_fraction_max 0.858
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.530
_diffrn_reflns_theta_min         4.649
_diffrn_ambient_temperature      295
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3048
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.964
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -71.00 -35.00   1.00    2.00    --  -22.88 123.00-102.00   36
  2  ω    -58.00  63.00   1.00    2.00    --  -22.88   8.00 147.00  121
  3  ω   -140.00-115.00   1.00    5.00    --  -70.50-129.00 -89.00   25
  4  ω   -161.00 -52.00   1.00    5.00    --  -70.50   8.00 147.00  109
  5  ω     79.00 113.00   1.00    5.00    --   71.94-141.00  97.00   34
  6  ω     95.00 161.00   1.00    5.00    --   71.94 123.00-102.00   66
  7  ω     37.00  73.00   1.00    5.00    --   71.94-141.00  97.00   36
  8  ω    136.00 162.00   1.00   12.00    --  121.00  -8.00 -27.00   26
  9  ω     27.00  53.00   1.00   12.00    --  121.00  -8.00 -27.00   26
 10  ω     94.00 135.00   1.00   12.00    --  121.00 129.00 -16.00   41
 11  ω     56.00  81.00   1.00   12.00    --  121.00-141.00  97.00   25
 12  ω     49.00  74.00   1.00   12.00    --  121.00-123.00 176.00   25
 13  ω     51.00  76.00   1.00   12.00    --  121.00-129.00 -89.00   25
 14  ω    102.00 128.00   1.00   12.00    --  121.00   8.00 147.00   26
 15  ω    112.00 137.00   1.00   12.00    --  121.00 123.00-102.00   25
 16  ω    101.00 161.00   1.00    5.00    --   71.94 111.00-150.00   60
 17  ω     51.00  76.00   1.00    5.00    --   71.94  -8.00 -27.00   25
 18  ω    107.00 162.00   1.00    5.00    --   71.94 111.00 -60.00   55
 19  ω     52.00  78.00   1.00   12.00    --  121.00 -63.00  60.00   26
 20  ω    108.00 175.00   1.00   12.00    --  121.00 111.00 -60.00   67
 21  ω     66.00  92.00   1.00   12.00    --  121.00 -91.00 -90.00   26
 22  ω     43.00  94.00   1.00   12.00    --  121.00-111.00  90.00   51
 23  ω    101.00 154.00   1.00   12.00    --  121.00 111.00-120.00   53
 24  ω     32.00 109.00   1.00   12.00    --  121.00-111.00 120.00   77
 25  ω    127.00 176.00   1.00   12.00    --  121.00 111.00 -30.00   49
 26  ω     56.00  91.00   1.00   12.00    --  121.00-111.00  30.00   35
 27  ω     24.00  60.00   1.00   12.00    --  121.00 -91.00 -90.00   36
 28  ω     61.00  86.00   1.00   12.00    --  121.00 178.00-120.00   25
 29  ω     98.00 124.00   1.00   12.00    --  121.00 -91.00 -90.00   26
 30  ω     42.00  67.00   1.00   12.00    --  121.00-111.00 -30.00   25
 31  ω     75.00 131.00   1.00   12.00    --  121.00  38.00  90.00   56
 32  ω     87.00 112.00   1.00   12.00    --  121.00-111.00 -30.00   25
 33  ω     60.00 112.00   1.00   12.00    --  121.00-111.00   0.00   52
 34  ω     86.00 124.00   1.00   12.00    --  121.00 178.00 -90.00   38
 35  ω     99.00 132.00   1.00   12.00    --  121.00-145.00 -32.30   33
 36  ω     82.00 111.00   1.00   12.00    --  121.00  50.00   0.00   29
 37  ω     88.00 161.00   1.00   12.00    --  121.00  77.00-150.00   73
 38  ω     35.00  60.00   1.00   12.00    --  121.00 -91.00-120.00   25
 39  ω    100.00 125.00   1.00   12.00    --  121.00 -91.00-120.00   25
 40  ω    102.00 176.00   1.00   12.00    --  121.00 111.00 -90.00   74
 41  ω     75.00 110.00   1.00   12.00    --  121.00-111.00  60.00   35
 42  ω    126.00 151.00   1.00   12.00    --  121.00 -63.00  60.00   25
 43  ω     98.00 123.00   1.00   12.00    --  121.00-132.00 -75.85   25
 44  ω     91.00 135.00   1.00   12.00    --  121.00-150.00  13.00   44
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0002232000
_diffrn_orient_matrix_UB_12      -0.0349527000
_diffrn_orient_matrix_UB_13      0.1187985000
_diffrn_orient_matrix_UB_21      0.0057381000
_diffrn_orient_matrix_UB_22      0.0444585000
_diffrn_orient_matrix_UB_23      0.0939643000
_diffrn_orient_matrix_UB_31      -0.0995198000
_diffrn_orient_matrix_UB_32      0.0025908000
_diffrn_orient_matrix_UB_33      0.0051500000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.742
_reflns_Friedel_fraction_full    0.780
_reflns_Friedel_fraction_max     0.747
_reflns_number_gt                6706
_reflns_number_total             7959
_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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.84a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.84a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.84a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.568
_refine_diff_density_min         -0.243
_refine_diff_density_rms         0.068
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.2(4)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     598
_refine_ls_number_reflns         7959
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0792
_refine_ls_R_factor_gt           0.0706
_refine_ls_restrained_S_all      1.040
_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)+(0.1336P)²+0.1614P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1815
_refine_ls_wR_factor_ref         0.1946
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.8(4)
 0.2(4)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3.a Ternary CH refined with riding coordinates:
 C1(H1), C14(H14), C28(H28), C29(H29)
3.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C6(H6), C7(H7), C9(H9), C16(H16), C17(H17), C18(H18),
 C19(H19), C20(H20), C22(H22), C23(H23), C24(H24), C25(H25), C34(H34), C36(H36),
  C37(H37), C39(H39), C40(H40), C43(H43), C44(H44), C45(H45), C46(H46),
 C47(H47), C49(H49), C50(H50), C51(H51), C52(H52)
3.c Idealised Me refined as rotating group:
 C27(H27A,H27B,H27C), C54(H54A,H54B,H54C)
;
_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 0.8725(2) 0.8792(3) 0.39869(15) 0.0559(8) Uani 1 1 d . . . . .
O2 O 0.7461(4) 0.8766(6) 0.4619(3) 0.108(2) Uani 1 1 d . . . . .
O3 O 0.7724(4) 0.6828(6) 0.48715(19) 0.0893(14) Uani 1 1 d . . . . .
O4 O 0.7252(3) 0.3766(4) 0.23650(15) 0.0702(10) Uani 1 1 d . . . . .
O5 O 0.6534(2) 0.5148(5) 0.38706(14) 0.0654(9) Uani 1 1 d . . . . .
N1 N 0.7861(3) 0.7756(6) 0.46089(17) 0.0608(10) Uani 1 1 d . . . . .
C1 C 0.8668(3) 0.7638(5) 0.42756(19) 0.0472(10) Uani 1 1 d . . . . .
H1 H 0.918886 0.754137 0.447675 0.057 Uiso 1 1 calc R U . . .
C2 C 0.8364(3) 0.8483(5) 0.35363(18) 0.0497(9) Uani 1 1 d . . . . .
C3 C 0.8243(3) 0.9428(5) 0.3176(2) 0.0587(11) Uani 1 1 d . . . . .
H3 H 0.835310 1.031545 0.323338 0.070 Uiso 1 1 calc R U . . .
C4 C 0.7951(3) 0.8984(5) 0.2729(2) 0.0600(11) Uani 1 1 d . . . . .
H4 H 0.787385 0.958489 0.247534 0.072 Uiso 1 1 calc R U . . .
C5 C 0.7765(3) 0.7641(6) 0.2645(2) 0.0525(11) Uani 1 1 d . . . . .
C6 C 0.7493(4) 0.7264(7) 0.2166(2) 0.0657(14) Uani 1 1 d . . . . .
H6 H 0.742336 0.791055 0.192731 0.079 Uiso 1 1 calc R U . . .
C7 C 0.7333(3) 0.5998(8) 0.20482(18) 0.0705(15) Uani 1 1 d . . . . .
H7 H 0.717819 0.574908 0.173160 0.085 Uiso 1 1 calc R U . . .
C8 C 0.7413(3) 0.5077(6) 0.24290(17) 0.0577(11) Uani 1 1 d . . . . .
C9 C 0.7367(4) 0.3210(6) 0.2819(2) 0.0647(12) Uani 1 1 d . . . . .
H9 H 0.729887 0.231543 0.288164 0.078 Uiso 1 1 calc R U . . .
C10 C 0.7591(2) 0.4101(5) 0.31664(17) 0.0487(9) Uani 1 1 d . . . . .
C11 C 0.7641(2) 0.5353(5) 0.29139(15) 0.0462(9) Uani 1 1 d . . . . .
C12 C 0.7867(2) 0.6684(4) 0.30286(14) 0.0430(8) Uani 1 1 d . . . . .
C13 C 0.8204(2) 0.7166(5) 0.34784(15) 0.0418(7) Uani 1 1 d . . . . .
C14 C 0.8575(2) 0.6460(4) 0.39287(14) 0.0403(8) Uani 1 1 d . . . . .
H14 H 0.816618 0.581127 0.405894 0.048 Uiso 1 1 calc R U . . .
C15 C 0.9458(2) 0.5850(4) 0.38448(15) 0.0424(7) Uani 1 1 d . . . . .
C16 C 0.9773(3) 0.4952(6) 0.4181(2) 0.0690(14) Uani 1 1 d . . . . .
H16 H 0.942556 0.468579 0.444096 0.083 Uiso 1 1 calc R U . . .
C17 C 1.0595(4) 0.4446(8) 0.4135(3) 0.088(2) Uani 1 1 d . . . . .
H17 H 1.079438 0.383440 0.436249 0.105 Uiso 1 1 calc R U . . .
C18 C 1.1123(3) 0.4839(6) 0.3756(3) 0.0723(15) Uani 1 1 d . . . . .
H18 H 1.168008 0.450466 0.372852 0.087 Uiso 1 1 calc R U . . .
C19 C 1.0821(3) 0.5725(7) 0.3419(2) 0.0702(14) Uani 1 1 d . . . . .
H19 H 1.117225 0.599009 0.316062 0.084 Uiso 1 1 calc R U . . .
C20 C 0.9989(3) 0.6231(5) 0.34626(19) 0.0545(10) Uani 1 1 d . . . . .
H20 H 0.978768 0.683255 0.323172 0.065 Uiso 1 1 calc R U . . .
C21 C 0.7640(3) 0.3673(4) 0.36867(18) 0.0497(9) Uani 1 1 d . . . . .
C22 C 0.8215(4) 0.2667(5) 0.3822(3) 0.0644(14) Uani 1 1 d . . . . .
H22 H 0.862184 0.236581 0.359753 0.077 Uiso 1 1 calc R U . . .
C23 C 0.8181(6) 0.2121(6) 0.4287(3) 0.087(2) Uani 1 1 d . . . . .
H23 H 0.855548 0.144122 0.437192 0.104 Uiso 1 1 calc R U . . .
C24 C 0.7595(6) 0.2586(7) 0.4622(3) 0.085(2) Uani 1 1 d . . . . .
H24 H 0.757369 0.221627 0.493384 0.102 Uiso 1 1 calc R U . . .
C25 C 0.7032(4) 0.3604(7) 0.4500(2) 0.0743(15) Uani 1 1 d . . . . .
H25 H 0.664119 0.391847 0.473163 0.089 Uiso 1 1 calc R U . . .
C26 C 0.7054(3) 0.4152(5) 0.40310(18) 0.0517(9) Uani 1 1 d . . . . .
C27 C 0.5925(4) 0.5669(11) 0.4208(3) 0.098(3) Uani 1 1 d . . . . .
H27A H 0.561414 0.637855 0.405636 0.148 Uiso 1 1 calc R U . . .
H27B H 0.622257 0.599135 0.449343 0.148 Uiso 1 1 calc R U . . .
H27C H 0.552741 0.498998 0.430346 0.148 Uiso 1 1 calc R U . . .
O6 O 0.6215(2) 0.8793(3) 0.60565(14) 0.0514(7) Uani 1 1 d . . . . .
O7 O 0.4921(4) 0.8815(6) 0.5454(2) 0.0996(18) Uani 1 1 d . . . . .
O8 O 0.5211(3) 0.6914(5) 0.51519(16) 0.0792(12) Uani 1 1 d . . . . .
O9 O 0.4698(3) 0.3640(6) 0.76020(19) 0.0874(15) Uani 1 1 d . . . . .
O10 O 0.4010(2) 0.5243(4) 0.61249(14) 0.0624(8) Uani 1 1 d . . . . .
N2 N 0.5358(3) 0.7835(5) 0.54291(16) 0.0572(9) Uani 1 1 d . . . . .
C28 C 0.6162(3) 0.7682(5) 0.57621(18) 0.0447(9) Uani 1 1 d . . . . .
H28 H 0.668374 0.760180 0.556056 0.054 Uiso 1 1 calc R U . . .
C29 C 0.6060(2) 0.6461(4) 0.60902(14) 0.0393(8) Uani 1 1 d . . . . .
H29 H 0.565696 0.582371 0.594671 0.047 Uiso 1 1 calc R U . . .
C30 C 0.5676(2) 0.7125(5) 0.65388(14) 0.0411(7) Uani 1 1 d . . . . .
C31 C 0.5318(2) 0.6618(5) 0.69840(14) 0.0447(8) Uani 1 1 d . . . . .
C32 C 0.5096(2) 0.5279(5) 0.70794(16) 0.0504(10) Uani 1 1 d . . . . .
C33 C 0.5038(3) 0.4041(5) 0.6807(2) 0.0568(11) Uani 1 1 d . . . . .
C34 C 0.4811(4) 0.3131(7) 0.7146(3) 0.0740(16) Uani 1 1 d . . . . .
H34 H 0.473967 0.224192 0.707402 0.089 Uiso 1 1 calc R U . . .
C35 C 0.4854(3) 0.4951(7) 0.7558(2) 0.0668(15) Uani 1 1 d . . . . .
C36 C 0.4760(4) 0.5840(9) 0.7946(2) 0.0795(19) Uani 1 1 d . . . . .
H36 H 0.459130 0.555880 0.825629 0.095 Uiso 1 1 calc R U . . .
C37 C 0.4924(4) 0.7127(10) 0.7853(2) 0.0783(19) Uani 1 1 d . . . . .
H37 H 0.485156 0.774738 0.810065 0.094 Uiso 1 1 calc R U . . .
C38 C 0.5208(3) 0.7544(5) 0.7377(2) 0.0538(12) Uani 1 1 d . . . . .
C39 C 0.5406(3) 0.8895(6) 0.7308(2) 0.0643(13) Uani 1 1 d . . . . .
H39 H 0.532653 0.947392 0.756908 0.077 Uiso 1 1 calc R U . . .
C40 C 0.5709(3) 0.9373(5) 0.6876(2) 0.0614(12) Uani 1 1 d . . . . .
H40 H 0.582402 1.026385 0.682989 0.074 Uiso 1 1 calc R U . . .
C41 C 0.5838(3) 0.8443(5) 0.65023(17) 0.0480(9) Uani 1 1 d . . . . .
C42 C 0.6939(2) 0.5847(4) 0.61821(14) 0.0401(7) Uani 1 1 d . . . . .
C43 C 0.7475(3) 0.6265(5) 0.65593(19) 0.0544(10) Uani 1 1 d . . . . .
H43 H 0.727664 0.689002 0.678191 0.065 Uiso 1 1 calc R U . . .
C44 C 0.8304(3) 0.5761(6) 0.6609(2) 0.0689(14) Uani 1 1 d . . . . .
H44 H 0.865775 0.605399 0.686248 0.083 Uiso 1 1 calc R U . . .
C45 C 0.8606(3) 0.4830(6) 0.6284(3) 0.0702(14) Uani 1 1 d . . . . .
H45 H 0.916317 0.449519 0.631556 0.084 Uiso 1 1 calc R U . . .
C46 C 0.8077(4) 0.4400(6) 0.5912(3) 0.0756(16) Uani 1 1 d . . . . .
H46 H 0.827553 0.377078 0.569112 0.091 Uiso 1 1 calc R U . . .
C47 C 0.7242(3) 0.4903(6) 0.5864(2) 0.0623(12) Uani 1 1 d . . . . .
H47 H 0.688623 0.459574 0.561356 0.075 Uiso 1 1 calc R U . . .
C48 C 0.5079(3) 0.3675(5) 0.6285(2) 0.0562(11) Uani 1 1 d . . . . .
C49 C 0.5613(5) 0.2659(5) 0.6109(3) 0.0747(18) Uani 1 1 d . . . . .
H49 H 0.601247 0.227524 0.632002 0.090 Uiso 1 1 calc R U . . .
C50 C 0.5560(6) 0.2217(7) 0.5632(4) 0.096(3) Uani 1 1 d . . . . .
H50 H 0.591602 0.153344 0.552748 0.115 Uiso 1 1 calc R U . . .
C51 C 0.4991(6) 0.2774(9) 0.5312(4) 0.098(3) Uani 1 1 d . . . . .
H51 H 0.495265 0.246418 0.499187 0.118 Uiso 1 1 calc R U . . .
C52 C 0.4470(4) 0.3804(7) 0.5466(3) 0.0751(16) Uani 1 1 d . . . . .
H52 H 0.409470 0.420180 0.524447 0.090 Uiso 1 1 calc R U . . .
C53 C 0.4500(3) 0.4241(5) 0.5942(2) 0.0561(10) Uani 1 1 d . . . . .
C54 C 0.3403(4) 0.5880(9) 0.5815(3) 0.090(2) Uani 1 1 d . . . . .
H54A H 0.370216 0.628916 0.554571 0.135 Uiso 1 1 calc R U . . .
H54B H 0.309768 0.653966 0.599813 0.135 Uiso 1 1 calc R U . . .
H54C H 0.300039 0.524423 0.568965 0.135 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 1.413(6) . ?
O1 C2 1.384(6) . ?
O2 N1 1.198(8) . ?
O3 N1 1.201(8) . ?
O4 C8 1.365(7) . ?
O4 C9 1.370(8) . ?
O5 C26 1.364(6) . ?
O5 C27 1.419(6) . ?
N1 C1 1.547(7) . ?
C1 H1 0.9800 . ?
C1 C14 1.531(6) . ?
C2 C3 1.385(7) . ?
C2 C13 1.369(6) . ?
C3 H3 0.9300 . ?
C3 C4 1.374(8) . ?
C4 H4 0.9300 . ?
C4 C5 1.412(8) . ?
C5 C6 1.423(8) . ?
C5 C12 1.435(7) . ?
C6 H6 0.9300 . ?
C6 C7 1.347(10) . ?
C7 H7 0.9300 . ?
C7 C8 1.402(9) . ?
C8 C11 1.395(6) . ?
C9 H9 0.9300 . ?
C9 C10 1.354(6) . ?
C10 C11 1.447(7) . ?
C10 C21 1.484(7) . ?
C11 C12 1.430(6) . ?
C12 C13 1.419(5) . ?
C13 C14 1.532(6) . ?
C14 H14 0.9800 . ?
C14 C15 1.516(5) . ?
C15 C16 1.380(6) . ?
C15 C20 1.381(6) . ?
C16 H16 0.9300 . ?
C16 C17 1.377(9) . ?
C17 H17 0.9300 . ?
C17 C18 1.376(10) . ?
C18 H18 0.9300 . ?
C18 C19 1.366(9) . ?
C19 H19 0.9300 . ?
C19 C20 1.391(7) . ?
C20 H20 0.9300 . ?
C21 C22 1.403(7) . ?
C21 C26 1.392(6) . ?
C22 H22 0.9300 . ?
C22 C23 1.383(10) . ?
C23 H23 0.9300 . ?
C23 C24 1.369(13) . ?
C24 H24 0.9300 . ?
C24 C25 1.392(12) . ?
C25 H25 0.9300 . ?
C25 C26 1.394(8) . ?
C27 H27A 0.9600 . ?
C27 H27B 0.9600 . ?
C27 H27C 0.9600 . ?
O6 C28 1.386(6) . ?
O6 C41 1.393(6) . ?
O7 N2 1.204(7) . ?
O8 N2 1.223(7) . ?
O9 C34 1.356(10) . ?
O9 C35 1.358(9) . ?
O10 C53 1.363(6) . ?
O10 C54 1.419(7) . ?
N2 C28 1.547(6) . ?
C28 H28 0.9800 . ?
C28 C29 1.536(6) . ?
C29 H29 0.9800 . ?
C29 C30 1.517(6) . ?
C29 C42 1.517(5) . ?
C30 C31 1.429(5) . ?
C30 C41 1.364(6) . ?
C31 C32 1.426(7) . ?
C31 C38 1.435(7) . ?
C32 C33 1.463(8) . ?
C32 C35 1.398(6) . ?
C33 C34 1.353(7) . ?
C33 C48 1.472(8) . ?
C34 H34 0.9300 . ?
C35 C36 1.396(10) . ?
C36 H36 0.9300 . ?
C36 C37 1.355(12) . ?
C37 H37 0.9300 . ?
C37 C38 1.432(8) . ?
C38 C39 1.417(9) . ?
C39 H39 0.9300 . ?
C39 C40 1.358(9) . ?
C40 H40 0.9300 . ?
C40 C41 1.402(6) . ?
C42 C43 1.387(6) . ?
C42 C47 1.374(6) . ?
C43 H43 0.9300 . ?
C43 C44 1.387(7) . ?
C44 H44 0.9300 . ?
C44 C45 1.377(9) . ?
C45 H45 0.9300 . ?
C45 C46 1.374(10) . ?
C46 H46 0.9300 . ?
C46 C47 1.394(7) . ?
C47 H47 0.9300 . ?
C48 C49 1.406(8) . ?
C48 C53 1.415(7) . ?
C49 H49 0.9300 . ?
C49 C50 1.376(13) . ?
C50 H50 0.9300 . ?
C50 C51 1.361(15) . ?
C51 H51 0.9300 . ?
C51 C52 1.385(12) . ?
C52 H52 0.9300 . ?
C52 C53 1.371(8) . ?
C54 H54A 0.9600 . ?
C54 H54B 0.9600 . ?
C54 H54C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 O1 C1 106.3(4) . . ?
C8 O4 C9 105.2(4) . . ?
C26 O5 C27 117.4(5) . . ?
O2 N1 O3 124.5(6) . . ?
O2 N1 C1 119.7(6) . . ?
O3 N1 C1 115.5(5) . . ?
O1 C1 N1 108.2(4) . . ?
O1 C1 H1 110.1 . . ?
O1 C1 C14 108.1(4) . . ?
N1 C1 H1 110.1 . . ?
C14 C1 N1 110.3(4) . . ?
C14 C1 H1 110.1 . . ?
O1 C2 C3 121.7(5) . . ?
C13 C2 O1 113.4(4) . . ?
C13 C2 C3 124.8(5) . . ?
C2 C3 H3 121.8 . . ?
C4 C3 C2 116.4(5) . . ?
C4 C3 H3 121.8 . . ?
C3 C4 H4 119.1 . . ?
C3 C4 C5 121.9(5) . . ?
C5 C4 H4 119.1 . . ?
C4 C5 C6 118.0(5) . . ?
C4 C5 C12 120.8(5) . . ?
C6 C5 C12 121.2(5) . . ?
C5 C6 H6 119.0 . . ?
C7 C6 C5 121.9(5) . . ?
C7 C6 H6 119.0 . . ?
C6 C7 H7 121.8 . . ?
C6 C7 C8 116.3(5) . . ?
C8 C7 H7 121.8 . . ?
O4 C8 C7 122.7(4) . . ?
O4 C8 C11 111.2(5) . . ?
C11 C8 C7 126.1(5) . . ?
O4 C9 H9 123.6 . . ?
C10 C9 O4 112.9(5) . . ?
C10 C9 H9 123.6 . . ?
C9 C10 C11 105.5(5) . . ?
C9 C10 C21 119.0(5) . . ?
C11 C10 C21 135.1(4) . . ?
C8 C11 C10 105.1(4) . . ?
C8 C11 C12 117.2(4) . . ?
C12 C11 C10 137.7(4) . . ?
C11 C12 C5 117.0(4) . . ?
C13 C12 C5 115.8(4) . . ?
C13 C12 C11 127.2(4) . . ?
C2 C13 C12 120.2(4) . . ?
C2 C13 C14 107.3(4) . . ?
C12 C13 C14 131.9(4) . . ?
C1 C14 C13 99.4(4) . . ?
C1 C14 H14 111.2 . . ?
C13 C14 H14 111.2 . . ?
C15 C14 C1 109.1(3) . . ?
C15 C14 C13 114.1(3) . . ?
C15 C14 H14 111.2 . . ?
C16 C15 C14 119.2(4) . . ?
C16 C15 C20 118.3(4) . . ?
C20 C15 C14 122.3(4) . . ?
C15 C16 H16 119.6 . . ?
C17 C16 C15 120.9(5) . . ?
C17 C16 H16 119.6 . . ?
C16 C17 H17 119.8 . . ?
C18 C17 C16 120.5(5) . . ?
C18 C17 H17 119.8 . . ?
C17 C18 H18 120.3 . . ?
C19 C18 C17 119.4(5) . . ?
C19 C18 H18 120.3 . . ?
C18 C19 H19 119.9 . . ?
C18 C19 C20 120.2(5) . . ?
C20 C19 H19 119.9 . . ?
C15 C20 C19 120.7(5) . . ?
C15 C20 H20 119.6 . . ?
C19 C20 H20 119.6 . . ?
C22 C21 C10 119.8(5) . . ?
C26 C21 C10 120.5(4) . . ?
C26 C21 C22 119.3(5) . . ?
C21 C22 H22 119.7 . . ?
C23 C22 C21 120.6(6) . . ?
C23 C22 H22 119.7 . . ?
C22 C23 H23 120.1 . . ?
C24 C23 C22 119.7(6) . . ?
C24 C23 H23 120.1 . . ?
C23 C24 H24 119.6 . . ?
C23 C24 C25 120.8(7) . . ?
C25 C24 H24 119.6 . . ?
C24 C25 H25 120.0 . . ?
C24 C25 C26 119.9(7) . . ?
C26 C25 H25 120.0 . . ?
O5 C26 C21 115.3(4) . . ?
O5 C26 C25 125.1(5) . . ?
C21 C26 C25 119.6(5) . . ?
O5 C27 H27A 109.5 . . ?
O5 C27 H27B 109.5 . . ?
O5 C27 H27C 109.5 . . ?
H27A C27 H27B 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C28 O6 C41 105.8(3) . . ?
C34 O9 C35 105.7(4) . . ?
C53 O10 C54 119.4(5) . . ?
O7 N2 O8 124.2(5) . . ?
O7 N2 C28 120.1(5) . . ?
O8 N2 C28 115.8(4) . . ?
O6 C28 N2 107.8(4) . . ?
O6 C28 H28 110.0 . . ?
O6 C28 C29 109.0(4) . . ?
N2 C28 H28 110.0 . . ?
C29 C28 N2 109.9(4) . . ?
C29 C28 H28 110.0 . . ?
C28 C29 H29 111.4 . . ?
C30 C29 C28 98.6(3) . . ?
C30 C29 H29 111.4 . . ?
C30 C29 C42 113.6(3) . . ?
C42 C29 C28 109.6(3) . . ?
C42 C29 H29 111.4 . . ?
C31 C30 C29 132.5(4) . . ?
C41 C30 C29 107.8(4) . . ?
C41 C30 C31 119.1(4) . . ?
C30 C31 C38 116.3(4) . . ?
C32 C31 C30 126.3(4) . . ?
C32 C31 C38 117.4(4) . . ?
C31 C32 C33 137.9(4) . . ?
C35 C32 C31 117.5(5) . . ?
C35 C32 C33 104.6(5) . . ?
C32 C33 C48 134.8(4) . . ?
C34 C33 C32 104.8(6) . . ?
C34 C33 C48 120.0(6) . . ?
O9 C34 H34 123.2 . . ?
C33 C34 O9 113.5(6) . . ?
C33 C34 H34 123.2 . . ?
O9 C35 C32 111.3(6) . . ?
O9 C35 C36 123.3(5) . . ?
C36 C35 C32 125.4(6) . . ?
C35 C36 H36 121.2 . . ?
C37 C36 C35 117.6(5) . . ?
C37 C36 H36 121.2 . . ?
C36 C37 H37 119.6 . . ?
C36 C37 C38 120.8(6) . . ?
C38 C37 H37 119.6 . . ?
C37 C38 C31 121.2(6) . . ?
C39 C38 C31 120.6(5) . . ?
C39 C38 C37 118.1(6) . . ?
C38 C39 H39 118.8 . . ?
C40 C39 C38 122.3(5) . . ?
C40 C39 H39 118.8 . . ?
C39 C40 H40 122.0 . . ?
C39 C40 C41 116.0(5) . . ?
C41 C40 H40 122.0 . . ?
O6 C41 C40 121.3(5) . . ?
C30 C41 O6 113.0(4) . . ?
C30 C41 C40 125.5(5) . . ?
C43 C42 C29 122.2(4) . . ?
C47 C42 C29 119.2(4) . . ?
C47 C42 C43 118.5(4) . . ?
C42 C43 H43 119.6 . . ?
C42 C43 C44 120.8(5) . . ?
C44 C43 H43 119.6 . . ?
C43 C44 H44 119.9 . . ?
C45 C44 C43 120.3(5) . . ?
C45 C44 H44 119.9 . . ?
C44 C45 H45 120.4 . . ?
C46 C45 C44 119.3(5) . . ?
C46 C45 H45 120.4 . . ?
C45 C46 H46 119.8 . . ?
C45 C46 C47 120.4(5) . . ?
C47 C46 H46 119.8 . . ?
C42 C47 C46 120.8(5) . . ?
C42 C47 H47 119.6 . . ?
C46 C47 H47 119.6 . . ?
C49 C48 C33 122.7(6) . . ?
C49 C48 C53 116.4(6) . . ?
C53 C48 C33 120.5(4) . . ?
C48 C49 H49 119.1 . . ?
C50 C49 C48 121.7(8) . . ?
C50 C49 H49 119.1 . . ?
C49 C50 H50 119.8 . . ?
C51 C50 C49 120.4(7) . . ?
C51 C50 H50 119.8 . . ?
C50 C51 H51 120.1 . . ?
C50 C51 C52 119.8(8) . . ?
C52 C51 H51 120.1 . . ?
C51 C52 H52 119.7 . . ?
C53 C52 C51 120.7(8) . . ?
C53 C52 H52 119.7 . . ?
O10 C53 C48 114.5(5) . . ?
O10 C53 C52 124.6(5) . . ?
C52 C53 C48 120.9(6) . . ?
O10 C54 H54A 109.5 . . ?
O10 C54 H54B 109.5 . . ?
O10 C54 H54C 109.5 . . ?
H54A C54 H54B 109.5 . . ?
H54A C54 H54C 109.5 . . ?
H54B C54 H54C 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 C14 C13 -23.5(5) . . . . ?
O1 C1 C14 C15 96.2(4) . . . . ?
O1 C2 C3 C4 174.4(4) . . . . ?
O1 C2 C13 C12 -177.5(3) . . . . ?
O1 C2 C13 C14 -5.6(5) . . . . ?
O2 N1 C1 O1 -6.6(7) . . . . ?
O2 N1 C1 C14 -124.6(6) . . . . ?
O3 N1 C1 O1 179.0(5) . . . . ?
O3 N1 C1 C14 60.9(6) . . . . ?
O4 C8 C11 C10 -1.6(5) . . . . ?
O4 C8 C11 C12 177.2(3) . . . . ?
O4 C9 C10 C11 -1.1(5) . . . . ?
O4 C9 C10 C21 173.1(4) . . . . ?
N1 C1 C14 C13 94.6(4) . . . . ?
N1 C1 C14 C15 -145.7(4) . . . . ?
C1 O1 C2 C3 174.1(4) . . . . ?
C1 O1 C2 C13 -10.1(5) . . . . ?
C1 C14 C15 C16 84.0(5) . . . . ?
C1 C14 C15 C20 -91.1(5) . . . . ?
C2 O1 C1 N1 -97.9(4) . . . . ?
C2 O1 C1 C14 21.6(5) . . . . ?
C2 C3 C4 C5 1.4(7) . . . . ?
C2 C13 C14 C1 17.3(4) . . . . ?
C2 C13 C14 C15 -98.7(4) . . . . ?
C3 C2 C13 C12 -1.9(7) . . . . ?
C3 C2 C13 C14 170.0(4) . . . . ?
C3 C4 C5 C6 -178.0(5) . . . . ?
C3 C4 C5 C12 0.7(7) . . . . ?
C4 C5 C6 C7 177.5(5) . . . . ?
C4 C5 C12 C11 178.4(4) . . . . ?
C4 C5 C12 C13 -3.3(6) . . . . ?
C5 C6 C7 C8 2.7(8) . . . . ?
C5 C12 C13 C2 3.8(6) . . . . ?
C5 C12 C13 C14 -165.8(4) . . . . ?
C6 C5 C12 C11 -3.0(6) . . . . ?
C6 C5 C12 C13 175.4(4) . . . . ?
C6 C7 C8 O4 178.5(5) . . . . ?
C6 C7 C8 C11 0.0(8) . . . . ?
C7 C8 C11 C10 177.1(4) . . . . ?
C7 C8 C11 C12 -4.1(6) . . . . ?
C8 O4 C9 C10 0.1(6) . . . . ?
C8 C11 C12 C5 5.3(5) . . . . ?
C8 C11 C12 C13 -172.8(4) . . . . ?
C9 O4 C8 C7 -177.8(5) . . . . ?
C9 O4 C8 C11 1.0(5) . . . . ?
C9 C10 C11 C8 1.6(5) . . . . ?
C9 C10 C11 C12 -176.8(4) . . . . ?
C9 C10 C21 C22 59.9(6) . . . . ?
C9 C10 C21 C26 -112.8(5) . . . . ?
C10 C11 C12 C5 -176.4(4) . . . . ?
C10 C11 C12 C13 5.4(7) . . . . ?
C10 C21 C22 C23 -170.4(5) . . . . ?
C10 C21 C26 O5 -8.8(6) . . . . ?
C10 C21 C26 C25 171.1(4) . . . . ?
C11 C10 C21 C22 -128.1(5) . . . . ?
C11 C10 C21 C26 59.2(6) . . . . ?
C11 C12 C13 C2 -178.0(4) . . . . ?
C11 C12 C13 C14 12.4(6) . . . . ?
C12 C5 C6 C7 -1.2(8) . . . . ?
C12 C13 C14 C1 -172.2(4) . . . . ?
C12 C13 C14 C15 71.9(5) . . . . ?
C13 C2 C3 C4 -0.9(7) . . . . ?
C13 C14 C15 C16 -165.8(4) . . . . ?
C13 C14 C15 C20 19.0(5) . . . . ?
C14 C15 C16 C17 -175.5(6) . . . . ?
C14 C15 C20 C19 174.9(5) . . . . ?
C15 C16 C17 C18 0.7(12) . . . . ?
C16 C15 C20 C19 -0.3(8) . . . . ?
C16 C17 C18 C19 -0.9(12) . . . . ?
C17 C18 C19 C20 0.5(11) . . . . ?
C18 C19 C20 C15 0.1(9) . . . . ?
C20 C15 C16 C17 -0.2(10) . . . . ?
C21 C10 C11 C8 -171.2(4) . . . . ?
C21 C10 C11 C12 10.4(8) . . . . ?
C21 C22 C23 C24 -1.5(10) . . . . ?
C22 C21 C26 O5 178.5(4) . . . . ?
C22 C21 C26 C25 -1.6(7) . . . . ?
C22 C23 C24 C25 -0.1(11) . . . . ?
C23 C24 C25 C26 0.8(10) . . . . ?
C24 C25 C26 O5 179.9(6) . . . . ?
C24 C25 C26 C21 0.1(8) . . . . ?
C26 C21 C22 C23 2.3(8) . . . . ?
C27 O5 C26 C21 180.0(6) . . . . ?
C27 O5 C26 C25 0.1(8) . . . . ?
O6 C28 C29 C30 24.1(4) . . . . ?
O6 C28 C29 C42 -94.9(4) . . . . ?
O7 N2 C28 O6 1.2(7) . . . . ?
O7 N2 C28 C29 119.9(6) . . . . ?
O8 N2 C28 O6 -178.6(5) . . . . ?
O8 N2 C28 C29 -59.9(6) . . . . ?
O9 C35 C36 C37 -179.0(5) . . . . ?
N2 C28 C29 C30 -93.8(4) . . . . ?
N2 C28 C29 C42 147.2(4) . . . . ?
C28 O6 C41 C30 10.1(5) . . . . ?
C28 O6 C41 C40 -174.2(4) . . . . ?
C28 C29 C30 C31 172.2(4) . . . . ?
C28 C29 C30 C41 -17.5(4) . . . . ?
C28 C29 C42 C43 86.0(5) . . . . ?
C28 C29 C42 C47 -89.8(5) . . . . ?
C29 C30 C31 C32 -11.8(6) . . . . ?
C29 C30 C31 C38 165.3(4) . . . . ?
C29 C30 C41 O6 6.0(4) . . . . ?
C29 C30 C41 C40 -169.5(4) . . . . ?
C29 C42 C43 C44 -174.5(5) . . . . ?
C29 C42 C47 C46 174.4(5) . . . . ?
C30 C29 C42 C43 -23.3(5) . . . . ?
C30 C29 C42 C47 161.0(4) . . . . ?
C30 C31 C32 C33 -7.9(7) . . . . ?
C30 C31 C32 C35 172.1(4) . . . . ?
C30 C31 C38 C37 -174.6(4) . . . . ?
C30 C31 C38 C39 3.3(6) . . . . ?
C31 C30 C41 O6 177.8(3) . . . . ?
C31 C30 C41 C40 2.3(6) . . . . ?
C31 C32 C33 C34 177.7(5) . . . . ?
C31 C32 C33 C48 -10.0(8) . . . . ?
C31 C32 C35 O9 -177.3(4) . . . . ?
C31 C32 C35 C36 4.2(7) . . . . ?
C31 C38 C39 C40 -0.3(7) . . . . ?
C32 C31 C38 C37 2.8(6) . . . . ?
C32 C31 C38 C39 -179.4(4) . . . . ?
C32 C33 C34 O9 1.3(6) . . . . ?
C32 C33 C48 C49 130.4(6) . . . . ?
C32 C33 C48 C53 -56.9(7) . . . . ?
C32 C35 C36 C37 -0.7(8) . . . . ?
C33 C32 C35 O9 2.7(5) . . . . ?
C33 C32 C35 C36 -175.8(5) . . . . ?
C33 C48 C49 C50 171.4(6) . . . . ?
C33 C48 C53 O10 8.4(6) . . . . ?
C33 C48 C53 C52 -172.8(5) . . . . ?
C34 O9 C35 C32 -2.0(6) . . . . ?
C34 O9 C35 C36 176.6(5) . . . . ?
C34 C33 C48 C49 -58.1(7) . . . . ?
C34 C33 C48 C53 114.5(5) . . . . ?
C35 O9 C34 C33 0.3(6) . . . . ?
C35 C32 C33 C34 -2.4(5) . . . . ?
C35 C32 C33 C48 170.0(5) . . . . ?
C35 C36 C37 C38 -1.8(8) . . . . ?
C36 C37 C38 C31 0.7(8) . . . . ?
C36 C37 C38 C39 -177.2(5) . . . . ?
C37 C38 C39 C40 177.6(5) . . . . ?
C38 C31 C32 C33 175.0(5) . . . . ?
C38 C31 C32 C35 -5.0(5) . . . . ?
C38 C39 C40 C41 -1.7(7) . . . . ?
C39 C40 C41 O6 -174.4(4) . . . . ?
C39 C40 C41 C30 0.8(7) . . . . ?
C41 O6 C28 N2 97.3(4) . . . . ?
C41 O6 C28 C29 -21.9(4) . . . . ?
C41 C30 C31 C32 178.8(4) . . . . ?
C41 C30 C31 C38 -4.1(5) . . . . ?
C42 C29 C30 C31 -71.8(5) . . . . ?
C42 C29 C30 C41 98.4(4) . . . . ?
C42 C43 C44 C45 -0.3(9) . . . . ?
C43 C42 C47 C46 -1.5(8) . . . . ?
C43 C44 C45 C46 -0.3(10) . . . . ?
C44 C45 C46 C47 0.1(10) . . . . ?
C45 C46 C47 C42 0.9(10) . . . . ?
C47 C42 C43 C44 1.3(8) . . . . ?
C48 C33 C34 O9 -172.4(5) . . . . ?
C48 C49 C50 C51 1.0(11) . . . . ?
C49 C48 C53 O10 -178.6(5) . . . . ?
C49 C48 C53 C52 0.3(7) . . . . ?
C49 C50 C51 C52 0.8(12) . . . . ?
C50 C51 C52 C53 -2.1(11) . . . . ?
C51 C52 C53 O10 -179.8(6) . . . . ?
C51 C52 C53 C48 1.5(9) . . . . ?
C53 C48 C49 C50 -1.5(8) . . . . ?
C54 O10 C53 C48 -179.7(5) . . . . ?
C54 O10 C53 C52 1.5(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
;
_oxdiff_exptl_absorpt_empirical_full_max 2.304
_oxdiff_exptl_absorpt_empirical_full_min 0.700
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.8(4)
2 0.2(4)

####################################################################### 
# 
# 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_ag2153f2
_database_code_depnum_ccdc_archive 'CCDC 2263637'
loop_
_audit_author_name
_audit_author_address
'Michel Giorgi'
;University of Aix Marseille
France
;
_audit_update_record             
;
2023-05-17 deposited with the CCDC.	2024-04-19 downloaded from the CCDC.
;
_audit_creation_date             2022-03-28
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C27 H18 Cl N O4'
_chemical_formula_sum            'C27 H18 Cl N O4'
_chemical_formula_weight         455.87
_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/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                   15.3160(5)
_cell_length_b                   9.2552(2)
_cell_length_c                   16.7635(5)
_cell_angle_alpha                90
_cell_angle_beta                 112.958(4)
_cell_angle_gamma                90
_cell_volume                     2188.05(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6371
_cell_measurement_temperature    295
_cell_measurement_theta_max      71.2690
_cell_measurement_theta_min      3.1110
_shelx_estimated_absorpt_T_max   0.914
_shelx_estimated_absorpt_T_min   0.710
_exptl_absorpt_coefficient_mu    1.841
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.87661
_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    1.384
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             944
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0257
_diffrn_reflns_av_unetI/netI     0.0273
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            14184
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.517
_diffrn_reflns_theta_min         3.134
_diffrn_ambient_temperature      295
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3048
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -80.00  17.00   1.00    5.00    --  -35.88  92.00  63.00   97
  2  ω   -126.00-101.00   1.00    5.00    --  -35.88 -92.00 -49.00   25
  3  ω     26.00  63.00   1.00    5.00    --   35.88 -92.00 -49.00   37
  4  ω    101.00 162.00   1.00   20.00    --  107.97  92.00  63.00   61
  5  ω     48.00 108.00   1.00   20.00    --  107.97 -92.00 -49.00   60
  6  ω   -125.00-100.00   1.00    5.00    --  -35.88 -99.00 -90.00   25
  7  ω   -124.00 -81.00   1.00    5.00    --  -35.88 -99.00-180.00   43
  8  ω   -124.00 -81.00   1.00    5.00    --  -35.88 -99.00  90.00   43
  9  ω   -105.00 -20.00   1.00    5.00    --  -35.88 -38.00-150.00   85
 10  ω   -119.00 -84.00   1.00    5.00    --  -35.88 -99.00-150.00   35
 11  ω   -121.00 -81.00   1.00    5.00    --  -35.88 -99.00-120.00   40
 12  ω   -124.00 -81.00   1.00    5.00    --  -35.88 -99.00 150.00   43
 13  ω     17.00  72.00   1.00    5.00    --   35.88 -77.00-120.00   55
 14  ω    -51.00 -26.00   1.00    5.00    --   35.88 -19.00   0.00   25
 15  ω     57.00 121.00   1.00    5.00    --   35.88 178.00 -60.00   64
 16  ω     90.00 115.00   1.00    5.00    --   35.88 -19.00   0.00   25
 17  ω    -55.00  -5.00   1.00    5.00    --   35.88 -77.00-120.00   50
 18  ω     59.00  95.00   1.00    5.00    --   35.88 178.00  60.00   36
 19  ω      5.00  43.00   1.00    5.00    --   35.88 -19.00   0.00   38
 20  ω     24.00 144.00   1.00   20.00    --  107.97 -61.00 -30.00  120
 21  ω    101.00 171.00   1.00   20.00    --  107.97 111.00  30.00   70
 22  ω     66.00 106.00   1.00   20.00    --  107.97 -94.00  60.00   40
 23  ω     72.00 177.00   1.00   20.00    --  107.97  45.00-150.00  105
 24  ω     22.00  50.00   1.00   20.00    --  107.97-111.00  60.00   28
 25  ω     22.00  47.00   1.00   20.00    --  107.97 -94.00  60.00   25
 26  ω    101.00 159.00   1.00   20.00    --  107.97  61.00 150.00   58
 27  ω     22.00  80.00   1.00   20.00    --  107.97-111.00-150.00   58
 28  ω     95.00 142.00   1.00   20.00    --  107.97  45.00  60.00   47
 29  ω     83.00 151.00   1.00   20.00    --  107.97  61.00 120.00   68
 30  ω     83.00 113.00   1.00   20.00    --  107.97-111.00  60.00   30
 31  ω    117.00 151.00   1.00   20.00    --  107.97 111.00  90.00   34
 32  ω     82.00 177.00   1.00   20.00    --  107.97  77.00   0.00   95
 33  ω     92.00 117.00   1.00   20.00    --  107.97 -45.00  30.00   25
 34  ω     60.00 110.00   1.00   20.00    --  107.97-111.00-120.00   50
 35  ω     64.00  89.00   1.00   20.00    --  107.97 -45.00  30.00   25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0459521000
_diffrn_orient_matrix_UB_12      -0.1509585000
_diffrn_orient_matrix_UB_13      0.0141140000
_diffrn_orient_matrix_UB_21      -0.0324112000
_diffrn_orient_matrix_UB_22      -0.0187943000
_diffrn_orient_matrix_UB_23      -0.0987240000
_diffrn_orient_matrix_UB_31      0.0936031000
_diffrn_orient_matrix_UB_32      0.0676182000
_diffrn_orient_matrix_UB_33      0.0042769000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3074
_reflns_number_total             4174
_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 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.288
_refine_diff_density_min         -0.385
_refine_diff_density_rms         0.054
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.132
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     299
_refine_ls_number_reflns         4174
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0671
_refine_ls_R_factor_gt           0.0473
_refine_ls_restrained_S_all      1.132
_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)+(0.0845P)²+0.6558P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1342
_refine_ls_wR_factor_ref         0.1692
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C10(H10), C11(H11)
2.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C7(H7), C8(H8), C17(H17), C18(H18), C19(H19), C20(H20),
 C23(H23), C24(H24), C25(H25), C26(H26), C27(H27)
2.c Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C)
;
_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
Cl1 Cl 0.34381(6) 0.68274(8) 0.35469(4) 0.0692(3) Uani 1 1 d . . . . .
O1 O 0.45523(14) 0.4888(2) 0.15445(12) 0.0575(5) Uani 1 1 d . . . . .
O2 O 0.00407(12) 0.5041(2) 0.18237(11) 0.0541(5) Uani 1 1 d . . . . .
O3 O 0.07398(18) 0.6579(2) 0.32462(15) 0.0780(7) Uani 1 1 d . . . . .
O4 O 0.1125(2) 0.4687(3) 0.40453(14) 0.0929(9) Uani 1 1 d . . . . .
N1 N 0.08282(17) 0.5286(3) 0.33483(14) 0.0549(6) Uani 1 1 d . . . . .
C1 C 0.38747(18) 0.4428(3) 0.24899(15) 0.0441(5) Uani 1 1 d . . . . .
C2 C 0.4678(2) 0.4357(3) 0.23506(17) 0.0536(6) Uani 1 1 d . . . . .
C3 C 0.3628(2) 0.5327(3) 0.11744(15) 0.0489(6) Uani 1 1 d . . . . .
C4 C 0.3267(2) 0.6070(3) 0.03872(17) 0.0572(7) Uani 1 1 d . . . . .
H4 H 0.362579 0.622442 0.005789 0.069 Uiso 1 1 calc R U . . .
C5 C 0.2363(2) 0.6552(3) 0.01310(16) 0.0552(7) Uani 1 1 d . . . . .
H5 H 0.210715 0.709552 -0.037399 0.066 Uiso 1 1 calc R U . . .
C6 C 0.17922(19) 0.6254(3) 0.06092(14) 0.0461(6) Uani 1 1 d . . . . .
C7 C 0.0854(2) 0.6766(3) 0.02968(15) 0.0545(7) Uani 1 1 d . . . . .
H7 H 0.063464 0.733535 -0.019957 0.065 Uiso 1 1 calc R U . . .
C8 C 0.0255(2) 0.6455(3) 0.06977(16) 0.0541(7) Uani 1 1 d . . . . .
H8 H -0.035863 0.682245 0.050032 0.065 Uiso 1 1 calc R U . . .
C9 C 0.06119(18) 0.5555(3) 0.14197(15) 0.0469(6) Uani 1 1 d . . . . .
C10 C 0.06282(18) 0.4301(3) 0.25640(15) 0.0463(6) Uani 1 1 d . . . . .
H10 H 0.032544 0.340278 0.263238 0.056 Uiso 1 1 calc R U . . .
C11 C 0.15738(17) 0.3975(3) 0.24775(14) 0.0413(5) Uani 1 1 d . . . . .
H11 H 0.210281 0.423400 0.301706 0.050 Uiso 1 1 calc R U . . .
C12 C 0.15190(16) 0.5039(3) 0.17741(14) 0.0397(5) Uani 1 1 d . . . . .
C13 C 0.21684(17) 0.5420(2) 0.13992(13) 0.0394(5) Uani 1 1 d . . . . .
C14 C 0.31529(18) 0.5038(2) 0.17081(14) 0.0406(5) Uani 1 1 d . . . . .
C15 C 0.38513(18) 0.4046(3) 0.33436(15) 0.0472(6) Uani 1 1 d . . . . .
C16 C 0.36970(19) 0.5053(3) 0.38880(16) 0.0531(7) Uani 1 1 d . . . . .
C17 C 0.3718(2) 0.4700(4) 0.46976(17) 0.0690(9) Uani 1 1 d . . . . .
H17 H 0.359657 0.540137 0.503838 0.083 Uiso 1 1 calc R U . . .
C18 C 0.3918(3) 0.3321(5) 0.4990(2) 0.0869(12) Uani 1 1 d . . . . .
H18 H 0.393289 0.307335 0.553334 0.104 Uiso 1 1 calc R U . . .
C19 C 0.4098(3) 0.2294(5) 0.4485(2) 0.0849(12) Uani 1 1 d . . . . .
H19 H 0.424688 0.135514 0.469143 0.102 Uiso 1 1 calc R U . . .
C20 C 0.4059(2) 0.2644(4) 0.3665(2) 0.0649(8) Uani 1 1 d . . . . .
H20 H 0.417371 0.193251 0.332588 0.078 Uiso 1 1 calc R U . . .
C21 C 0.5663(2) 0.3908(5) 0.2897(2) 0.0769(10) Uani 1 1 d . . . . .
H21A H 0.584023 0.310239 0.263202 0.115 Uiso 1 1 calc R U . . .
H21B H 0.569757 0.363343 0.346105 0.115 Uiso 1 1 calc R U . . .
H21C H 0.608870 0.469912 0.295230 0.115 Uiso 1 1 calc R U . . .
C22 C 0.16534(17) 0.2383(3) 0.22718(14) 0.0400(5) Uani 1 1 d . . . . .
C23 C 0.1791(2) 0.1375(3) 0.29154(17) 0.0534(6) Uani 1 1 d . . . . .
H23 H 0.184333 0.167858 0.346107 0.064 Uiso 1 1 calc R U . . .
C24 C 0.1852(2) -0.0077(3) 0.27608(19) 0.0601(7) Uani 1 1 d . . . . .
H24 H 0.193599 -0.074539 0.319876 0.072 Uiso 1 1 calc R U . . .
C25 C 0.1788(2) -0.0534(3) 0.1966(2) 0.0630(8) Uani 1 1 d . . . . .
H25 H 0.183227 -0.151331 0.186325 0.076 Uiso 1 1 calc R U . . .
C26 C 0.1659(3) 0.0452(3) 0.13216(19) 0.0714(9) Uani 1 1 d . . . . .
H26 H 0.161445 0.013962 0.077972 0.086 Uiso 1 1 calc R U . . .
C27 C 0.1595(2) 0.1910(3) 0.14715(16) 0.0569(7) Uani 1 1 d . . . . .
H27 H 0.151167 0.257398 0.103144 0.068 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
Cl1 C16 1.733(3) . ?
O1 C2 1.379(3) . ?
O1 C3 1.367(3) . ?
O2 C9 1.383(3) . ?
O2 C10 1.396(3) . ?
O3 N1 1.210(3) . ?
O4 N1 1.210(3) . ?
N1 C10 1.529(3) . ?
C1 C2 1.341(4) . ?
C1 C14 1.459(3) . ?
C1 C15 1.488(3) . ?
C2 C21 1.487(4) . ?
C3 C4 1.397(4) . ?
C3 C14 1.382(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.354(4) . ?
C5 H5 0.9300 . ?
C5 C6 1.425(4) . ?
C6 C7 1.406(4) . ?
C6 C13 1.444(3) . ?
C7 H7 0.9300 . ?
C7 C8 1.363(4) . ?
C8 H8 0.9300 . ?
C8 C9 1.393(4) . ?
C9 C12 1.367(3) . ?
C10 H10 0.9800 . ?
C10 C11 1.541(3) . ?
C11 H11 0.9800 . ?
C11 C12 1.513(3) . ?
C11 C22 1.528(3) . ?
C12 C13 1.413(3) . ?
C13 C14 1.434(3) . ?
C15 C16 1.388(4) . ?
C15 C20 1.393(4) . ?
C16 C17 1.384(4) . ?
C17 H17 0.9300 . ?
C17 C18 1.360(5) . ?
C18 H18 0.9300 . ?
C18 C19 1.371(6) . ?
C19 H19 0.9300 . ?
C19 C20 1.391(5) . ?
C20 H20 0.9300 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 C23 1.379(3) . ?
C22 C27 1.380(3) . ?
C23 H23 0.9300 . ?
C23 C24 1.378(4) . ?
C24 H24 0.9300 . ?
C24 C25 1.364(4) . ?
C25 H25 0.9300 . ?
C25 C26 1.369(4) . ?
C26 H26 0.9300 . ?
C26 C27 1.383(4) . ?
C27 H27 0.9300 . ?

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
C3 O1 C2 105.9(2) . . ?
C9 O2 C10 107.02(19) . . ?
O3 N1 O4 124.7(3) . . ?
O3 N1 C10 119.6(2) . . ?
O4 N1 C10 115.5(2) . . ?
C2 C1 C14 106.7(2) . . ?
C2 C1 C15 121.6(2) . . ?
C14 C1 C15 131.4(2) . . ?
O1 C2 C21 115.1(2) . . ?
C1 C2 O1 111.5(2) . . ?
C1 C2 C21 133.3(3) . . ?
O1 C3 C4 122.2(2) . . ?
O1 C3 C14 111.2(2) . . ?
C14 C3 C4 126.3(3) . . ?
C3 C4 H4 121.9 . . ?
C5 C4 C3 116.2(2) . . ?
C5 C4 H4 121.9 . . ?
C4 C5 H5 118.9 . . ?
C4 C5 C6 122.2(2) . . ?
C6 C5 H5 118.9 . . ?
C5 C6 C13 120.4(2) . . ?
C7 C6 C5 119.2(2) . . ?
C7 C6 C13 120.4(2) . . ?
C6 C7 H7 118.9 . . ?
C8 C7 C6 122.1(2) . . ?
C8 C7 H7 118.9 . . ?
C7 C8 H8 121.9 . . ?
C7 C8 C9 116.3(3) . . ?
C9 C8 H8 121.9 . . ?
O2 C9 C8 121.5(2) . . ?
C12 C9 O2 113.4(2) . . ?
C12 C9 C8 125.1(3) . . ?
O2 C10 N1 108.4(2) . . ?
O2 C10 H10 110.5 . . ?
O2 C10 C11 108.4(2) . . ?
N1 C10 H10 110.5 . . ?
N1 C10 C11 108.50(19) . . ?
C11 C10 H10 110.5 . . ?
C10 C11 H11 109.5 . . ?
C12 C11 C10 100.21(19) . . ?
C12 C11 H11 109.5 . . ?
C12 C11 C22 115.87(18) . . ?
C22 C11 C10 111.8(2) . . ?
C22 C11 H11 109.5 . . ?
C9 C12 C11 107.7(2) . . ?
C9 C12 C13 119.5(2) . . ?
C13 C12 C11 132.4(2) . . ?
C12 C13 C6 116.3(2) . . ?
C12 C13 C14 127.0(2) . . ?
C14 C13 C6 116.7(2) . . ?
C3 C14 C1 104.5(2) . . ?
C3 C14 C13 117.6(2) . . ?
C13 C14 C1 137.8(2) . . ?
C16 C15 C1 123.1(2) . . ?
C16 C15 C20 116.3(2) . . ?
C20 C15 C1 120.4(3) . . ?
C15 C16 Cl1 119.69(19) . . ?
C17 C16 Cl1 117.5(3) . . ?
C17 C16 C15 122.8(3) . . ?
C16 C17 H17 120.3 . . ?
C18 C17 C16 119.4(3) . . ?
C18 C17 H17 120.3 . . ?
C17 C18 H18 120.0 . . ?
C17 C18 C19 119.9(3) . . ?
C19 C18 H18 120.0 . . ?
C18 C19 H19 119.7 . . ?
C18 C19 C20 120.5(3) . . ?
C20 C19 H19 119.7 . . ?
C15 C20 H20 119.5 . . ?
C19 C20 C15 121.0(3) . . ?
C19 C20 H20 119.5 . . ?
C2 C21 H21A 109.5 . . ?
C2 C21 H21B 109.5 . . ?
C2 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C23 C22 C11 118.5(2) . . ?
C23 C22 C27 118.5(2) . . ?
C27 C22 C11 123.0(2) . . ?
C22 C23 H23 119.6 . . ?
C24 C23 C22 120.9(2) . . ?
C24 C23 H23 119.6 . . ?
C23 C24 H24 119.9 . . ?
C25 C24 C23 120.1(3) . . ?
C25 C24 H24 119.9 . . ?
C24 C25 H25 120.1 . . ?
C24 C25 C26 119.8(3) . . ?
C26 C25 H25 120.1 . . ?
C25 C26 H26 119.8 . . ?
C25 C26 C27 120.4(3) . . ?
C27 C26 H26 119.8 . . ?
C22 C27 C26 120.3(3) . . ?
C22 C27 H27 119.9 . . ?
C26 C27 H27 119.9 . . ?

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
Cl1 C16 C17 C18 180.0(3) . . . . ?
O1 C3 C4 C5 -174.4(2) . . . . ?
O1 C3 C14 C1 2.8(3) . . . . ?
O1 C3 C14 C13 -179.0(2) . . . . ?
O2 C9 C12 C11 3.4(3) . . . . ?
O2 C9 C12 C13 177.0(2) . . . . ?
O2 C10 C11 C12 17.8(2) . . . . ?
O2 C10 C11 C22 -105.5(2) . . . . ?
O3 N1 C10 O2 -21.9(3) . . . . ?
O3 N1 C10 C11 95.7(3) . . . . ?
O4 N1 C10 O2 162.4(3) . . . . ?
O4 N1 C10 C11 -80.0(3) . . . . ?
N1 C10 C11 C12 -99.7(2) . . . . ?
N1 C10 C11 C22 137.0(2) . . . . ?
C1 C15 C16 Cl1 4.5(4) . . . . ?
C1 C15 C16 C17 -177.0(3) . . . . ?
C1 C15 C20 C19 176.0(3) . . . . ?
C2 O1 C3 C4 173.0(3) . . . . ?
C2 O1 C3 C14 -2.4(3) . . . . ?
C2 C1 C14 C3 -2.1(3) . . . . ?
C2 C1 C14 C13 -179.7(3) . . . . ?
C2 C1 C15 C16 111.7(3) . . . . ?
C2 C1 C15 C20 -63.3(4) . . . . ?
C3 O1 C2 C1 0.9(3) . . . . ?
C3 O1 C2 C21 -175.9(3) . . . . ?
C3 C4 C5 C6 -3.4(4) . . . . ?
C4 C3 C14 C1 -172.3(3) . . . . ?
C4 C3 C14 C13 5.8(4) . . . . ?
C4 C5 C6 C7 -178.8(3) . . . . ?
C4 C5 C6 C13 0.4(4) . . . . ?
C5 C6 C7 C8 176.5(3) . . . . ?
C5 C6 C13 C12 -173.0(2) . . . . ?
C5 C6 C13 C14 5.6(3) . . . . ?
C6 C7 C8 C9 -2.2(4) . . . . ?
C6 C13 C14 C1 169.0(3) . . . . ?
C6 C13 C14 C3 -8.3(3) . . . . ?
C7 C6 C13 C12 6.2(3) . . . . ?
C7 C6 C13 C14 -175.2(2) . . . . ?
C7 C8 C9 O2 -173.0(2) . . . . ?
C7 C8 C9 C12 3.7(4) . . . . ?
C8 C9 C12 C11 -173.6(2) . . . . ?
C8 C9 C12 C13 0.0(4) . . . . ?
C9 O2 C10 N1 100.9(2) . . . . ?
C9 O2 C10 C11 -16.7(3) . . . . ?
C9 C12 C13 C6 -4.9(3) . . . . ?
C9 C12 C13 C14 176.7(2) . . . . ?
C10 O2 C9 C8 -174.3(2) . . . . ?
C10 O2 C9 C12 8.6(3) . . . . ?
C10 C11 C12 C9 -12.5(2) . . . . ?
C10 C11 C12 C13 175.1(2) . . . . ?
C10 C11 C22 C23 -71.8(3) . . . . ?
C10 C11 C22 C27 108.3(3) . . . . ?
C11 C12 C13 C6 166.8(2) . . . . ?
C11 C12 C13 C14 -11.6(4) . . . . ?
C11 C22 C23 C24 178.9(3) . . . . ?
C11 C22 C27 C26 -179.1(3) . . . . ?
C12 C11 C22 C23 174.3(2) . . . . ?
C12 C11 C22 C27 -5.6(3) . . . . ?
C12 C13 C14 C1 -12.6(4) . . . . ?
C12 C13 C14 C3 170.1(2) . . . . ?
C13 C6 C7 C8 -2.7(4) . . . . ?
C14 C1 C2 O1 0.8(3) . . . . ?
C14 C1 C2 C21 176.8(3) . . . . ?
C14 C1 C15 C16 -62.0(4) . . . . ?
C14 C1 C15 C20 123.0(3) . . . . ?
C14 C3 C4 C5 0.2(4) . . . . ?
C15 C1 C2 O1 -174.3(2) . . . . ?
C15 C1 C2 C21 1.7(5) . . . . ?
C15 C1 C14 C3 172.3(3) . . . . ?
C15 C1 C14 C13 -5.3(5) . . . . ?
C15 C16 C17 C18 1.5(5) . . . . ?
C16 C15 C20 C19 0.6(4) . . . . ?
C16 C17 C18 C19 0.1(5) . . . . ?
C17 C18 C19 C20 -1.3(6) . . . . ?
C18 C19 C20 C15 0.9(5) . . . . ?
C20 C15 C16 Cl1 179.8(2) . . . . ?
C20 C15 C16 C17 -1.8(4) . . . . ?
C22 C11 C12 C9 107.9(2) . . . . ?
C22 C11 C12 C13 -64.5(3) . . . . ?
C22 C23 C24 C25 0.9(5) . . . . ?
C23 C22 C27 C26 1.0(4) . . . . ?
C23 C24 C25 C26 -0.3(5) . . . . ?
C24 C25 C26 C27 0.1(5) . . . . ?
C25 C26 C27 C22 -0.5(5) . . . . ?
C27 C22 C23 C24 -1.2(4) . . . . ?

_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 1.404
_oxdiff_exptl_absorpt_empirical_full_min 0.798
####################################################################### 
# 
# 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_eyp1-12
_database_code_depnum_ccdc_archive 'CCDC 2263639'
loop_
_audit_author_name
_audit_author_address
'Michel Giorgi'
;University of Aix Marseille
France
;
_audit_update_record             
;
2023-05-17 deposited with the CCDC.	2024-04-19 downloaded from the CCDC.
;
_audit_creation_date             2022-01-28
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C27 H19 N O4'
_chemical_formula_sum            'C27 H19 N O4'
_chemical_formula_weight         421.43
_chemical_melting_point          ?

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      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                   8.7947(2)
_cell_length_b                   9.7683(2)
_cell_length_c                   13.6750(3)
_cell_angle_alpha                78.591(2)
_cell_angle_beta                 74.221(2)
_cell_angle_gamma                66.162(2)
_cell_volume                     1028.93(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    11441
_cell_measurement_temperature    295
_cell_measurement_theta_max      72.6090
_cell_measurement_theta_min      3.3430
_shelx_estimated_absorpt_T_max   0.929
_shelx_estimated_absorpt_T_min   0.916
_exptl_absorpt_coefficient_mu    0.744
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.90910
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.122a (Rigaku Oxford Diffraction, 2021)
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    1.360
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             440
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0266
_diffrn_reflns_av_unetI/netI     0.0155
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            18898
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.747
_diffrn_reflns_theta_min         3.375
_diffrn_ambient_temperature      295
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3048
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -110.00 -65.00   1.00    5.00    --  -40.79 -52.00 -32.00   45
  2  ω     19.00  46.00   1.00    5.00    --   40.79  52.00 113.00   27
  3  ω     66.00  99.00   1.00    5.00    --   40.79  52.00 113.00   33
  4  ω     37.00  63.00   1.00   20.00    --  105.59 -52.00 -32.00   26
  5  ω    117.00 143.00   1.00   20.00    --  105.59  52.00 113.00   26
  6  ω     81.00 111.00   1.00   20.00    --  105.59  52.00 113.00   30
  7  ω    -56.00 -16.00   1.00    5.00    --  -40.79 -52.00 -32.00   40
  8  ω     -9.00  19.00   1.00    5.00    --  -40.79  52.00 113.00   28
  9  ω    -55.00 -19.00   1.00    5.00    --  -40.79  52.00 113.00   36
 10  ω     19.00  45.00   1.00    5.00    --   40.79  38.00  60.00   26
 11  ω    -29.00  67.00   1.00    5.00    --   40.79 -52.00 -32.00   96
 12  ω     48.00 113.00   1.00    5.00    --   40.79  38.00  60.00   65
 13  ω     25.00  97.00   1.00    5.00    --   40.79-125.00-120.00   72
 14  ω     17.00  42.00   1.00    5.00    --   46.00  67.00 174.16   25
 15  ω     55.00  82.00   1.00    5.00    --   46.00  67.00 174.16   27
 16  ω     11.00  36.00   1.00    5.00    --   46.00  84.00-172.15   25
 17  ω     11.00  37.00   1.00    5.00    --   46.00  84.00 -90.36   26
 18  ω     11.00  36.00   1.00    5.00    --   46.00  84.00 -31.27   25
 19  ω     16.00  42.00   1.00    5.00    --   50.00  81.00 150.93   26
 20  ω     17.00  43.00   1.00    5.00    --   50.00  80.00  62.62   26
 21  ω     17.00  42.00   1.00    5.00    --   50.00  79.00 119.94   25
 22  ω     71.00  97.00   1.00    5.00    --   58.00  75.00-110.93   26
 23  ω     25.00  54.00   1.00    5.00    --   58.00  77.00  22.90   29
 24  ω     27.00  65.00   1.00    5.00    --   58.00  75.00-110.93   38
 25  ω     26.00  62.00   1.00    5.00    --   58.00  75.00 -41.14   36
 26  ω     32.00  60.00   1.00    5.00    --   62.00  75.00 121.98   28
 27  ω     31.00  56.00   1.00    5.00    --   62.00  76.00-165.31   25
 28  ω     35.00  69.00   1.00    5.00    --   66.00  76.00  64.36   34
 29  ω     98.00 124.00   1.00    5.00    --   66.00  76.00 -27.22   26
 30  ω     34.00  66.00   1.00    5.00    --   66.00  76.00 -27.22   32
 31  ω     92.00 142.00   1.00    5.00    --   66.00  76.00  64.36   50
 32  ω     39.00 142.00   1.00    5.00    --   70.00  76.00-107.36  103
 33  ω     43.00  69.00   1.00    5.00    --   70.00  61.00  67.04   26
 34  ω     45.00  71.00   1.00   20.00    --   74.00  65.00  19.17   26
 35  ω     42.00  70.00   1.00   20.00    --   74.00  75.00 141.27   28
 36  ω     46.00  75.00   1.00   20.00    --   78.00  77.00 166.85   29
 37  ω    104.00 153.00   1.00   20.00    --   78.00  74.00 104.22   49
 38  ω     46.00  74.00   1.00   20.00    --   78.00  74.00 104.22   28
 39  ω     51.00  83.00   1.00   20.00    --   82.00  72.00-141.98   32
 40  ω     53.00  93.00   1.00   20.00    --   82.00  67.00 -62.72   40
 41  ω     57.00  83.00   1.00   20.00    --   86.00  71.00-178.38   26
 42  ω     56.00  95.00   1.00   20.00    --   86.00  65.00 -85.40   39
 43  ω    124.00 157.00   1.00   20.00    --   90.00  75.00 -54.61   33
 44  ω     62.00 112.00   1.00   20.00    --   90.00  75.00 -54.61   50
 45  ω     69.00 104.00   1.00   20.00    --  105.59 -94.00  60.00   35
 46  ω    115.00 147.00   1.00   20.00    --  105.59  77.00  60.00   32
 47  ω     33.00  63.00   1.00   20.00    --  105.59 -94.00  60.00   30
 48  ω     77.00 105.00   1.00   20.00    --  105.59  77.00  60.00   28
 49  ω     73.00 173.00   1.00   20.00    --  105.59  77.00   0.00  100
 50  ω     24.00 108.00   1.00   20.00    --  105.59 -94.00   0.00   84
 51  ω     73.00 101.00   1.00   20.00    --  105.59  77.00 120.00   28
 52  ω     81.00 128.00   1.00   20.00    --  105.59  61.00   0.00   47
 53  ω    112.00 177.00   1.00   20.00    --  105.59  77.00  90.00   65
 54  ω     73.00 177.00   1.00   20.00    --  105.59  77.00  30.00  104
 55  ω     75.00 102.00   1.00   20.00    --  105.59  77.00  90.00   27
 56  ω     75.00 143.00   1.00   20.00    --  105.59  77.00-180.00   68
 57  ω     74.00 178.00   1.00   20.00    --  105.59  77.00-120.00  104
 58  ω    109.00 148.00   1.00   20.00    --  105.59  77.00 -90.00   39
 59  ω     75.00 101.00   1.00   20.00    --  105.59  77.00 -90.00   26
 60  ω     73.00 177.00   1.00   20.00    --  105.59  77.00 -60.00  104
 61  ω     44.00 111.00   1.00   20.00    --  105.59-125.00 -30.00   67
 62  ω     74.00 177.00   1.00   20.00    --  105.59  77.00-150.00  103
 63  ω     36.00  98.00   1.00   20.00    --  105.59 -94.00-150.00   62
 64  ω     77.00 178.00   1.00   20.00    --  105.59  61.00 150.00  101
 65  ω    125.00 151.00   1.00   20.00    --  105.59  77.00 -30.00   26
 66  ω     73.00  99.00   1.00   20.00    --  105.59  77.00 -30.00   26
 67  ω     44.00 116.00   1.00   20.00    --  105.59-125.00-180.00   72
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1770995000
_diffrn_orient_matrix_UB_12      -0.0028858000
_diffrn_orient_matrix_UB_13      0.0539478000
_diffrn_orient_matrix_UB_21      -0.0409968000
_diffrn_orient_matrix_UB_22      0.1417147000
_diffrn_orient_matrix_UB_23      0.0509523000
_diffrn_orient_matrix_UB_31      -0.0734263000
_diffrn_orient_matrix_UB_32      0.0996821000
_diffrn_orient_matrix_UB_33      -0.0913027000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3629
_reflns_number_total             4028
_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 1.171.41.122a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.122a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.122a (Rigaku OD, 2021)'
_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         0.240
_refine_diff_density_min         -0.250
_refine_diff_density_rms         0.035
_refine_ls_extinction_coef       0.0032(6)
_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   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     290
_refine_ls_number_reflns         4028
_refine_ls_number_restraints     18
_refine_ls_R_factor_all          0.0469
_refine_ls_R_factor_gt           0.0435
_refine_ls_restrained_S_all      1.056
_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)+(0.0687P)²+0.2186P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1221
_refine_ls_wR_factor_ref         0.1260
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Rigid body (RIGU) restrains
 C1, N1, O3, O4
 with sigma for 1-2 distances of 0.0005 and sigma for 1-3 distances of 0.001
3.a Ternary CH refined with riding coordinates:
 C1(H1), C15(H15)
3.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B)
3.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C6(H6), C7(H7), C10(H10), C17(H17), C18(H18), C19(H19),
 C20(H20), C21(H21), C23(H23), C24(H24), C25(H25), C26(H26), C27(H27)
;
_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 0.06355(14) 0.57296(12) 0.57983(8) 0.0614(3) Uani 1 1 d . . . . .
O2 O 0.63086(15) -0.15321(11) 0.73780(9) 0.0610(3) Uani 1 1 d . . . . .
O3 O 0.1173(3) 0.74261(17) 0.67812(14) 0.1111(7) Uani 1 1 d . . . . .
O4 O -0.0168(2) 0.67687(15) 0.82302(11) 0.0832(4) Uani 1 1 d . . . . .
N1 N 0.03989(17) 0.66918(13) 0.73202(12) 0.0607(3) Uani 1 1 d . . . . .
C1 C 0.00657(18) 0.55516(15) 0.68529(11) 0.0503(3) Uani 1 1 d . . . . .
H1 H -0.114813 0.571582 0.702885 0.060 Uiso 1 1 calc R U . . .
C2 C 0.22517(18) 0.46205(16) 0.55668(11) 0.0485(3) Uani 1 1 d . . . . .
C3 C 0.3263(2) 0.45558(19) 0.45838(12) 0.0571(4) Uani 1 1 d . . . . .
H3 H 0.296567 0.532206 0.406486 0.069 Uiso 1 1 calc R U . . .
C4 C 0.4711(2) 0.33097(18) 0.44245(11) 0.0536(4) Uani 1 1 d . . . . .
H4 H 0.541824 0.322114 0.377741 0.064 Uiso 1 1 calc R U . . .
C5 C 0.51736(17) 0.21460(16) 0.52118(10) 0.0443(3) Uani 1 1 d . . . . .
C6 C 0.65861(18) 0.07902(18) 0.49854(12) 0.0530(4) Uani 1 1 d . . . . .
H6 H 0.729129 0.072467 0.433769 0.064 Uiso 1 1 calc R U . . .
C7 C 0.69234(19) -0.04132(17) 0.57004(13) 0.0556(4) Uani 1 1 d . . . . .
H7 H 0.780025 -0.131960 0.552997 0.067 Uiso 1 1 calc R U . . .
C8 C 0.59386(18) -0.02746(15) 0.66949(12) 0.0474(3) Uani 1 1 d . . . . .
C9 C 0.4891(2) -0.14791(17) 0.82256(13) 0.0612(4) Uani 1 1 d . . . . .
H9A H 0.522375 -0.235798 0.871125 0.073 Uiso 1 1 calc R U . . .
H9B H 0.395230 -0.147946 0.798252 0.073 Uiso 1 1 calc R U . . .
C10 C 0.4349(2) -0.00906(16) 0.87303(12) 0.0517(4) Uani 1 1 d . . . . .
H10 H 0.410818 -0.011143 0.943750 0.062 Uiso 1 1 calc R U . . .
C11 C 0.42213(17) 0.11903(14) 0.81243(10) 0.0414(3) Uani 1 1 d . . . . .
C12 C 0.47007(16) 0.10871(13) 0.70116(10) 0.0394(3) Uani 1 1 d . . . . .
C13 C 0.41779(15) 0.22831(14) 0.62295(10) 0.0380(3) Uani 1 1 d . . . . .
C14 C 0.26546(16) 0.35808(14) 0.63766(10) 0.0399(3) Uani 1 1 d . . . . .
C15 C 0.11256(16) 0.39530(13) 0.72607(10) 0.0406(3) Uani 1 1 d . . . . .
H15 H 0.147180 0.399550 0.787390 0.049 Uiso 1 1 calc R U . . .
C16 C 0.39535(17) 0.25864(14) 0.85397(10) 0.0414(3) Uani 1 1 d . . . . .
C17 C 0.48021(18) 0.35312(15) 0.79969(11) 0.0459(3) Uani 1 1 d . . . . .
H17 H 0.552619 0.329275 0.736604 0.055 Uiso 1 1 calc R U . . .
C18 C 0.4579(2) 0.48189(18) 0.83860(13) 0.0575(4) Uani 1 1 d . . . . .
H18 H 0.516130 0.543380 0.801783 0.069 Uiso 1 1 calc R U . . .
C19 C 0.3505(3) 0.51956(19) 0.93118(13) 0.0649(4) Uani 1 1 d . . . . .
H19 H 0.334260 0.607203 0.956518 0.078 Uiso 1 1 calc R U . . .
C20 C 0.2672(2) 0.42690(19) 0.98623(12) 0.0627(4) Uani 1 1 d . . . . .
H20 H 0.194974 0.451741 1.049232 0.075 Uiso 1 1 calc R U . . .
C21 C 0.2899(2) 0.29672(17) 0.94846(11) 0.0518(3) Uani 1 1 d . . . . .
H21 H 0.234023 0.234246 0.986817 0.062 Uiso 1 1 calc R U . . .
C22 C 0.02328(16) 0.28469(14) 0.74830(11) 0.0435(3) Uani 1 1 d . . . . .
C23 C -0.0025(2) 0.23091(19) 0.66993(14) 0.0596(4) Uani 1 1 d . . . . .
H23 H 0.030410 0.266561 0.602495 0.072 Uiso 1 1 calc R U . . .
C24 C -0.0769(2) 0.1248(2) 0.6914(2) 0.0789(6) Uani 1 1 d . . . . .
H24 H -0.093936 0.089671 0.638343 0.095 Uiso 1 1 calc R U . . .
C25 C -0.1254(2) 0.0711(2) 0.7902(2) 0.0847(7) Uani 1 1 d . . . . .
H25 H -0.173966 -0.001228 0.804164 0.102 Uiso 1 1 calc R U . . .
C26 C -0.1025(3) 0.1240(2) 0.86894(19) 0.0826(6) Uani 1 1 d . . . . .
H26 H -0.136157 0.087831 0.936138 0.099 Uiso 1 1 calc R U . . .
C27 C -0.0291(2) 0.23147(19) 0.84812(13) 0.0613(4) Uani 1 1 d . . . . .
H27 H -0.014974 0.267904 0.901602 0.074 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.3926(18) . ?
O1 C2 1.3931(17) . ?
O2 C8 1.3696(18) . ?
O2 C9 1.445(2) . ?
O3 N1 1.1974(18) . ?
O4 N1 1.2133(19) . ?
N1 C1 1.543(2) . ?
C1 H1 0.9800 . ?
C1 C15 1.5428(17) . ?
C2 C3 1.393(2) . ?
C2 C14 1.3641(19) . ?
C3 H3 0.9300 . ?
C3 C4 1.361(2) . ?
C4 H4 0.9300 . ?
C4 C5 1.413(2) . ?
C5 C6 1.420(2) . ?
C5 C13 1.4275(18) . ?
C6 H6 0.9300 . ?
C6 C7 1.359(2) . ?
C7 H7 0.9300 . ?
C7 C8 1.398(2) . ?
C8 C12 1.3939(18) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 C10 1.487(2) . ?
C10 H10 0.9300 . ?
C10 C11 1.3386(19) . ?
C11 C12 1.4767(19) . ?
C11 C16 1.4873(18) . ?
C12 C13 1.4350(18) . ?
C13 C14 1.4226(18) . ?
C14 C15 1.5155(17) . ?
C15 H15 0.9800 . ?
C15 C22 1.5173(18) . ?
C16 C17 1.3944(19) . ?
C16 C21 1.388(2) . ?
C17 H17 0.9300 . ?
C17 C18 1.383(2) . ?
C18 H18 0.9300 . ?
C18 C19 1.372(2) . ?
C19 H19 0.9300 . ?
C19 C20 1.375(2) . ?
C20 H20 0.9300 . ?
C20 C21 1.386(2) . ?
C21 H21 0.9300 . ?
C22 C23 1.388(2) . ?
C22 C27 1.384(2) . ?
C23 H23 0.9300 . ?
C23 C24 1.383(3) . ?
C24 H24 0.9300 . ?
C24 C25 1.368(3) . ?
C25 H25 0.9300 . ?
C25 C26 1.374(3) . ?
C26 H26 0.9300 . ?
C26 C27 1.389(3) . ?
C27 H27 0.9300 . ?

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 O1 C2 106.73(10) . . ?
C8 O2 C9 112.37(11) . . ?
O3 N1 O4 124.88(17) . . ?
O3 N1 C1 119.38(15) . . ?
O4 N1 C1 115.75(13) . . ?
O1 C1 N1 107.84(12) . . ?
O1 C1 H1 110.7 . . ?
O1 C1 C15 108.58(11) . . ?
N1 C1 H1 110.7 . . ?
C15 C1 N1 108.19(12) . . ?
C15 C1 H1 110.7 . . ?
C3 C2 O1 122.01(13) . . ?
C14 C2 O1 112.87(12) . . ?
C14 C2 C3 124.96(13) . . ?
C2 C3 H3 121.8 . . ?
C4 C3 C2 116.32(13) . . ?
C4 C3 H3 121.8 . . ?
C3 C4 H4 119.0 . . ?
C3 C4 C5 122.05(13) . . ?
C5 C4 H4 119.0 . . ?
C4 C5 C6 120.09(13) . . ?
C4 C5 C13 120.62(13) . . ?
C6 C5 C13 119.21(13) . . ?
C5 C6 H6 119.5 . . ?
C7 C6 C5 121.03(14) . . ?
C7 C6 H6 119.5 . . ?
C6 C7 H7 120.3 . . ?
C6 C7 C8 119.32(13) . . ?
C8 C7 H7 120.3 . . ?
O2 C8 C7 116.85(13) . . ?
O2 C8 C12 120.39(13) . . ?
C12 C8 C7 122.65(13) . . ?
O2 C9 H9A 109.8 . . ?
O2 C9 H9B 109.8 . . ?
O2 C9 C10 109.15(12) . . ?
H9A C9 H9B 108.3 . . ?
C10 C9 H9A 109.8 . . ?
C10 C9 H9B 109.8 . . ?
C9 C10 H10 121.4 . . ?
C11 C10 C9 117.23(14) . . ?
C11 C10 H10 121.4 . . ?
C10 C11 C12 116.97(12) . . ?
C10 C11 C16 121.29(13) . . ?
C12 C11 C16 120.61(11) . . ?
C8 C12 C11 115.62(12) . . ?
C8 C12 C13 117.10(12) . . ?
C13 C12 C11 126.85(11) . . ?
C5 C13 C12 119.02(12) . . ?
C14 C13 C5 116.34(12) . . ?
C14 C13 C12 124.51(12) . . ?
C2 C14 C13 119.47(12) . . ?
C2 C14 C15 108.19(11) . . ?
C13 C14 C15 131.32(11) . . ?
C1 C15 H15 109.9 . . ?
C14 C15 C1 99.65(10) . . ?
C14 C15 H15 109.9 . . ?
C14 C15 C22 112.95(11) . . ?
C22 C15 C1 114.16(11) . . ?
C22 C15 H15 109.9 . . ?
C17 C16 C11 120.45(12) . . ?
C21 C16 C11 121.46(12) . . ?
C21 C16 C17 118.07(13) . . ?
C16 C17 H17 119.6 . . ?
C18 C17 C16 120.75(14) . . ?
C18 C17 H17 119.6 . . ?
C17 C18 H18 119.8 . . ?
C19 C18 C17 120.45(14) . . ?
C19 C18 H18 119.8 . . ?
C18 C19 H19 120.2 . . ?
C18 C19 C20 119.58(14) . . ?
C20 C19 H19 120.2 . . ?
C19 C20 H20 119.8 . . ?
C19 C20 C21 120.45(15) . . ?
C21 C20 H20 119.8 . . ?
C16 C21 H21 119.7 . . ?
C20 C21 C16 120.68(14) . . ?
C20 C21 H21 119.7 . . ?
C23 C22 C15 121.27(13) . . ?
C27 C22 C15 120.04(14) . . ?
C27 C22 C23 118.65(14) . . ?
C22 C23 H23 119.7 . . ?
C24 C23 C22 120.51(18) . . ?
C24 C23 H23 119.7 . . ?
C23 C24 H24 119.9 . . ?
C25 C24 C23 120.3(2) . . ?
C25 C24 H24 119.9 . . ?
C24 C25 H25 119.9 . . ?
C24 C25 C26 120.11(17) . . ?
C26 C25 H25 119.9 . . ?
C25 C26 H26 120.0 . . ?
C25 C26 C27 119.97(19) . . ?
C27 C26 H26 120.0 . . ?
C22 C27 C26 120.45(19) . . ?
C22 C27 H27 119.8 . . ?
C26 C27 H27 119.8 . . ?

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 C15 C14 19.60(14) . . . . ?
O1 C1 C15 C22 -101.05(14) . . . . ?
O1 C2 C3 C4 -171.36(15) . . . . ?
O1 C2 C14 C13 172.75(12) . . . . ?
O1 C2 C14 C15 3.02(17) . . . . ?
O2 C8 C12 C11 17.32(18) . . . . ?
O2 C8 C12 C13 -169.67(11) . . . . ?
O2 C9 C10 C11 44.67(19) . . . . ?
O3 N1 C1 O1 -6.2(2) . . . . ?
O3 N1 C1 C15 111.08(18) . . . . ?
O4 N1 C1 O1 173.68(14) . . . . ?
O4 N1 C1 C15 -69.06(17) . . . . ?
N1 C1 C15 C14 -97.18(12) . . . . ?
N1 C1 C15 C22 142.17(12) . . . . ?
C1 O1 C2 C3 -174.10(15) . . . . ?
C1 O1 C2 C14 10.21(17) . . . . ?
C1 C15 C22 C23 71.44(17) . . . . ?
C1 C15 C22 C27 -110.77(15) . . . . ?
C2 O1 C1 N1 98.11(13) . . . . ?
C2 O1 C1 C15 -18.90(16) . . . . ?
C2 C3 C4 C5 -0.3(2) . . . . ?
C2 C14 C15 C1 -13.30(14) . . . . ?
C2 C14 C15 C22 108.23(13) . . . . ?
C3 C2 C14 C13 -2.8(2) . . . . ?
C3 C2 C14 C15 -172.52(14) . . . . ?
C3 C4 C5 C6 172.65(15) . . . . ?
C3 C4 C5 C13 -3.9(2) . . . . ?
C4 C5 C6 C7 -171.56(14) . . . . ?
C4 C5 C13 C12 -179.14(12) . . . . ?
C4 C5 C13 C14 4.78(18) . . . . ?
C5 C6 C7 C8 -4.8(2) . . . . ?
C5 C13 C14 C2 -1.59(18) . . . . ?
C5 C13 C14 C15 165.38(13) . . . . ?
C6 C5 C13 C12 4.26(18) . . . . ?
C6 C5 C13 C14 -171.83(12) . . . . ?
C6 C7 C8 O2 178.53(13) . . . . ?
C6 C7 C8 C12 -5.2(2) . . . . ?
C7 C8 C12 C11 -158.81(13) . . . . ?
C7 C8 C12 C13 14.2(2) . . . . ?
C8 O2 C9 C10 -56.08(16) . . . . ?
C8 C12 C13 C5 -13.38(18) . . . . ?
C8 C12 C13 C14 162.36(12) . . . . ?
C9 O2 C8 C7 -157.57(13) . . . . ?
C9 O2 C8 C12 26.08(18) . . . . ?
C9 C10 C11 C12 -2.5(2) . . . . ?
C9 C10 C11 C16 -170.40(13) . . . . ?
C10 C11 C12 C8 -29.60(18) . . . . ?
C10 C11 C12 C13 158.17(13) . . . . ?
C10 C11 C16 C17 139.79(15) . . . . ?
C10 C11 C16 C21 -38.3(2) . . . . ?
C11 C12 C13 C5 158.74(12) . . . . ?
C11 C12 C13 C14 -25.5(2) . . . . ?
C11 C16 C17 C18 -178.99(14) . . . . ?
C11 C16 C21 C20 179.66(14) . . . . ?
C12 C11 C16 C17 -27.71(18) . . . . ?
C12 C11 C16 C21 154.15(13) . . . . ?
C12 C13 C14 C2 -177.43(12) . . . . ?
C12 C13 C14 C15 -10.5(2) . . . . ?
C13 C5 C6 C7 5.1(2) . . . . ?
C13 C14 C15 C1 178.63(14) . . . . ?
C13 C14 C15 C22 -59.84(19) . . . . ?
C14 C2 C3 C4 3.8(2) . . . . ?
C14 C15 C22 C23 -41.49(17) . . . . ?
C14 C15 C22 C27 136.30(14) . . . . ?
C15 C22 C23 C24 176.91(14) . . . . ?
C15 C22 C27 C26 -176.47(15) . . . . ?
C16 C11 C12 C8 138.43(13) . . . . ?
C16 C11 C12 C13 -33.80(19) . . . . ?
C16 C17 C18 C19 -0.5(2) . . . . ?
C17 C16 C21 C20 1.5(2) . . . . ?
C17 C18 C19 C20 1.2(3) . . . . ?
C18 C19 C20 C21 -0.5(3) . . . . ?
C19 C20 C21 C16 -0.9(3) . . . . ?
C21 C16 C17 C18 -0.8(2) . . . . ?
C22 C23 C24 C25 -0.2(3) . . . . ?
C23 C22 C27 C26 1.4(2) . . . . ?
C23 C24 C25 C26 0.8(3) . . . . ?
C24 C25 C26 C27 -0.4(3) . . . . ?
C25 C26 C27 C22 -0.8(3) . . . . ?
C27 C22 C23 C24 -0.9(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 1.382
_oxdiff_exptl_absorpt_empirical_full_min 0.807
####################################################################### 
# 
# 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_eyp291
_database_code_depnum_ccdc_archive 'CCDC 2263640'
loop_
_audit_author_name
_audit_author_address
'Michel Giorgi'
;University of Aix Marseille
France
;
_audit_update_record             
;
2023-05-17 deposited with the CCDC.	2024-04-19 downloaded from the CCDC.
;
_audit_creation_date             2023-01-30
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C27 H17 N O5'
_chemical_formula_sum            'C27 H17 N O5'
_chemical_formula_weight         435.42
_chemical_melting_point          ?
_chemical_oxdiff_formula         'c27 h17 n1 o5'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   10.9082(6)
_cell_length_b                   13.4620(7)
_cell_length_c                   28.2100(13)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4142.5(4)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    6592
_cell_measurement_temperature    295
_cell_measurement_theta_max      70.3350
_cell_measurement_theta_min      5.1240
_shelx_estimated_absorpt_T_max   0.910
_shelx_estimated_absorpt_T_min   0.784
_exptl_absorpt_coefficient_mu    0.798
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.89214
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.79a (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    1.396
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             1808
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0312
_diffrn_reflns_av_unetI/netI     0.0290
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.917
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            12209
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.917
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.591
_diffrn_reflns_theta_min         5.126
_diffrn_ambient_temperature      295
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3048
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.917
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω      0.00  51.00   1.00    1.00    --    0.00 -96.00 103.00   51
  2  ω    -95.00  16.00   1.00    5.00    --  -55.48  58.00 -17.00  111
  3  ω   -146.00-120.00   1.00    5.00    --  -55.48 -72.00 -12.00   26
  4  ω     -1.00  41.00   1.00    5.00    --   55.48 -96.00 103.00   42
  5  ω     66.00 146.00   1.00   20.00    --  110.96  72.00 117.00   80
  6  ω    115.00 140.00   1.00   20.00    --  110.96  96.00-147.00   25
  7  ω     36.00  66.00   1.00   20.00    --  110.96 -96.00 103.00   30
  8  ω     30.00 145.00   1.00   20.00    --  110.96 -58.00-158.00  115
  9  ω     57.00  82.00   1.00    1.00    --    0.00 178.00 -60.00   25
 10  ω     13.00  48.00   1.00    1.00    --    0.00 -99.00 -60.00   35
 11  ω      3.00  48.00   1.00    1.00    --    0.00 -99.00-150.00   45
 12  ω    -92.00  -2.00   1.00    5.00    --  -55.48 125.00 -30.00   90
 13  ω     33.00 102.00   1.00    5.00    --   55.48-125.00-150.00   69
 14  ω    149.00 176.00   1.00   20.00    --  110.96  50.00  30.00   27
 15  ω    143.00 169.00   1.00   20.00    --  110.96 111.00 -30.00   26
 16  ω     71.00 144.00   1.00   20.00    --  110.96  50.00  30.00   73
 17  ω    126.00 152.00   1.00   20.00    --  110.96 111.00-180.00   26
 18  ω     60.00 178.00   1.00   20.00    --  110.96  38.00  90.00  118
 19  ω     67.00  93.00   1.00   20.00    --  110.96  77.00 -90.00   26
 20  ω     34.00 106.00   1.00   20.00    --  110.96-111.00-150.00   72
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0783580000
_diffrn_orient_matrix_UB_12      -0.0016541000
_diffrn_orient_matrix_UB_13      0.0453456000
_diffrn_orient_matrix_UB_21      -0.0838137000
_diffrn_orient_matrix_UB_22      -0.0794355000
_diffrn_orient_matrix_UB_23      -0.0223482000
_diffrn_orient_matrix_UB_31      0.0823653000
_diffrn_orient_matrix_UB_32      -0.0824014000
_diffrn_orient_matrix_UB_33      0.0206044000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2964
_reflns_number_total             3947
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.79a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.79a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.79a (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         0.404
_refine_diff_density_min         -0.341
_refine_diff_density_rms         0.079
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.132
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     300
_refine_ls_number_reflns         3947
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0970
_refine_ls_R_factor_gt           0.0661
_refine_ls_restrained_S_all      1.132
_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)+(0.1531P)²+4.1543P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2310
_refine_ls_wR_factor_ref         0.2934
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1), C15(H15)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C6(H6), C7(H7), C10(H10), C17(H17), C18(H18), C19(H19),
 C20(H20), C21(H21), C23(H23), C24(H24), C25(H25), C26(H26), C27(H27)
;
_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 0.5413(3) 0.4662(2) 0.55145(10) 0.0629(10) Uani 1 1 d . . . . .
O2 O 0.1301(3) 0.7844(3) 0.68413(11) 0.0701(11) Uani 1 1 d . . . . .
O3 O 0.1728(4) 0.9287(3) 0.71744(14) 0.0898(13) Uani 1 1 d . . . . .
O4 O 0.6913(5) 0.4280(3) 0.62085(16) 0.1042(15) Uani 1 1 d . . . . .
O5 O 0.7995(3) 0.5575(4) 0.60624(16) 0.1013(15) Uani 1 1 d . . . . .
N1 N 0.7104(4) 0.5052(3) 0.60069(14) 0.0675(12) Uani 1 1 d . . . . .
C1 C 0.6161(4) 0.5441(3) 0.56502(13) 0.0548(11) Uani 1 1 d . . . . .
H1 H 0.657869 0.572031 0.537290 0.066 Uiso 1 1 calc R U . . .
C2 C 0.4309(4) 0.4777(3) 0.57536(13) 0.0529(11) Uani 1 1 d . . . . .
C3 C 0.3377(5) 0.4078(3) 0.57000(15) 0.0649(13) Uani 1 1 d . . . . .
H3 H 0.350065 0.347810 0.554328 0.078 Uiso 1 1 calc R U . . .
C4 C 0.2282(5) 0.4328(3) 0.58907(15) 0.0639(13) Uani 1 1 d . . . . .
H4 H 0.162191 0.389767 0.585201 0.077 Uiso 1 1 calc R U . . .
C5 C 0.2103(4) 0.5218(3) 0.61462(14) 0.0542(11) Uani 1 1 d . . . . .
C6 C 0.0910(4) 0.5481(4) 0.62958(15) 0.0670(13) Uani 1 1 d . . . . .
H6 H 0.027039 0.503579 0.624837 0.080 Uiso 1 1 calc R U . . .
C7 C 0.0676(4) 0.6354(4) 0.65039(16) 0.0707(14) Uani 1 1 d . . . . .
H7 H -0.012637 0.653989 0.657220 0.085 Uiso 1 1 calc R U . . .
C8 C 0.1655(4) 0.6985(3) 0.66177(13) 0.0561(11) Uani 1 1 d . . . . .
C9 C 0.2130(5) 0.8537(3) 0.70058(15) 0.0656(13) Uani 1 1 d . . . . .
C10 C 0.3385(5) 0.8236(3) 0.69847(14) 0.0595(12) Uani 1 1 d . . . . .
H10 H 0.397457 0.864812 0.711864 0.071 Uiso 1 1 calc R U . . .
C11 C 0.3758(4) 0.7376(3) 0.67785(11) 0.0454(10) Uani 1 1 d . . . . .
C12 C 0.2878(3) 0.6753(3) 0.65311(12) 0.0448(10) Uani 1 1 d . . . . .
C13 C 0.3105(3) 0.5889(3) 0.62374(11) 0.0429(9) Uani 1 1 d . . . . .
C14 C 0.4218(4) 0.5646(2) 0.60029(11) 0.0445(10) Uani 1 1 d . . . . .
C15 C 0.5363(3) 0.6242(2) 0.58898(12) 0.0427(10) Uani 1 1 d . . . . .
H15 H 0.575214 0.647126 0.618320 0.051 Uiso 1 1 calc R U . . .
C16 C 0.5164(3) 0.7113(2) 0.55538(12) 0.0444(10) Uani 1 1 d . . . . .
C17 C 0.4221(4) 0.7116(3) 0.52211(14) 0.0543(11) Uani 1 1 d . . . . .
H17 H 0.363889 0.661089 0.522302 0.065 Uiso 1 1 calc R U . . .
C18 C 0.4148(5) 0.7866(3) 0.48879(15) 0.0668(13) Uani 1 1 d . . . . .
H18 H 0.351984 0.786171 0.466519 0.080 Uiso 1 1 calc R U . . .
C19 C 0.5004(5) 0.8622(3) 0.48838(16) 0.0701(14) Uani 1 1 d . . . . .
H19 H 0.496418 0.911897 0.465523 0.084 Uiso 1 1 calc R U . . .
C20 C 0.5910(5) 0.8634(3) 0.52190(18) 0.0710(14) Uani 1 1 d . . . . .
H20 H 0.647282 0.915295 0.522201 0.085 Uiso 1 1 calc R U . . .
C21 C 0.6002(4) 0.7890(3) 0.55521(15) 0.0586(12) Uani 1 1 d . . . . .
H21 H 0.662738 0.790728 0.577618 0.070 Uiso 1 1 calc R U . . .
C22 C 0.5036(3) 0.7053(2) 0.68846(11) 0.0428(10) Uani 1 1 d . . . . .
C23 C 0.6017(4) 0.7716(3) 0.68494(13) 0.0549(11) Uani 1 1 d . . . . .
H23 H 0.588189 0.836553 0.674944 0.066 Uiso 1 1 calc R U . . .
C24 C 0.7183(4) 0.7408(4) 0.69627(15) 0.0675(13) Uani 1 1 d . . . . .
H24 H 0.783468 0.784718 0.692861 0.081 Uiso 1 1 calc R U . . .
C25 C 0.7401(4) 0.6463(4) 0.71254(15) 0.0677(13) Uani 1 1 d . . . . .
H25 H 0.819298 0.626440 0.720204 0.081 Uiso 1 1 calc R U . . .
C26 C 0.6430(4) 0.5811(3) 0.71739(14) 0.0611(12) Uani 1 1 d . . . . .
H26 H 0.656722 0.517366 0.728990 0.073 Uiso 1 1 calc R U . . .
C27 C 0.5257(4) 0.6101(3) 0.70510(12) 0.0486(10) Uani 1 1 d . . . . .
H27 H 0.461123 0.565353 0.708004 0.058 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.384(5) . ?
O1 C2 1.389(5) . ?
O2 C8 1.373(5) . ?
O2 C9 1.379(6) . ?
O3 C9 1.199(5) . ?
O4 N1 1.203(5) . ?
O5 N1 1.210(6) . ?
N1 C1 1.531(5) . ?
C1 H1 0.9800 . ?
C1 C15 1.542(5) . ?
C2 C3 1.393(6) . ?
C2 C14 1.369(5) . ?
C3 H3 0.9300 . ?
C3 C4 1.354(7) . ?
C4 H4 0.9300 . ?
C4 C5 1.411(6) . ?
C5 C6 1.414(6) . ?
C5 C13 1.441(5) . ?
C6 H6 0.9300 . ?
C6 C7 1.338(7) . ?
C7 H7 0.9300 . ?
C7 C8 1.402(7) . ?
C8 C12 1.392(5) . ?
C9 C10 1.429(7) . ?
C10 H10 0.9300 . ?
C10 C11 1.358(5) . ?
C11 C12 1.452(5) . ?
C11 C22 1.491(5) . ?
C12 C13 1.449(5) . ?
C13 C14 1.421(5) . ?
C14 C15 1.518(5) . ?
C15 H15 0.9800 . ?
C15 C16 1.523(5) . ?
C16 C17 1.392(5) . ?
C16 C21 1.389(5) . ?
C17 H17 0.9300 . ?
C17 C18 1.382(6) . ?
C18 H18 0.9300 . ?
C18 C19 1.381(7) . ?
C19 H19 0.9300 . ?
C19 C20 1.368(7) . ?
C20 H20 0.9300 . ?
C20 C21 1.377(6) . ?
C21 H21 0.9300 . ?
C22 C23 1.398(5) . ?
C22 C27 1.386(5) . ?
C23 H23 0.9300 . ?
C23 C24 1.375(6) . ?
C24 H24 0.9300 . ?
C24 C25 1.373(7) . ?
C25 H25 0.9300 . ?
C25 C26 1.383(7) . ?
C26 H26 0.9300 . ?
C26 C27 1.382(6) . ?
C27 H27 0.9300 . ?

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 O1 C2 107.0(3) . . ?
C8 O2 C9 122.7(3) . . ?
O4 N1 O5 125.5(5) . . ?
O4 N1 C1 119.3(4) . . ?
O5 N1 C1 115.1(4) . . ?
O1 C1 N1 108.6(3) . . ?
O1 C1 H1 110.1 . . ?
O1 C1 C15 108.5(3) . . ?
N1 C1 H1 110.1 . . ?
N1 C1 C15 109.3(3) . . ?
C15 C1 H1 110.1 . . ?
O1 C2 C3 120.3(3) . . ?
C14 C2 O1 114.0(3) . . ?
C14 C2 C3 125.5(4) . . ?
C2 C3 H3 122.2 . . ?
C4 C3 C2 115.7(4) . . ?
C4 C3 H3 122.2 . . ?
C3 C4 H4 118.8 . . ?
C3 C4 C5 122.4(4) . . ?
C5 C4 H4 118.8 . . ?
C4 C5 C6 119.5(4) . . ?
C4 C5 C13 121.3(4) . . ?
C6 C5 C13 119.1(4) . . ?
C5 C6 H6 119.1 . . ?
C7 C6 C5 121.8(4) . . ?
C7 C6 H6 119.1 . . ?
C6 C7 H7 120.4 . . ?
C6 C7 C8 119.1(4) . . ?
C8 C7 H7 120.4 . . ?
O2 C8 C7 113.7(4) . . ?
O2 C8 C12 122.6(4) . . ?
C12 C8 C7 123.7(4) . . ?
O2 C9 C10 115.0(4) . . ?
O3 C9 O2 117.6(5) . . ?
O3 C9 C10 127.3(5) . . ?
C9 C10 H10 118.4 . . ?
C11 C10 C9 123.1(4) . . ?
C11 C10 H10 118.4 . . ?
C10 C11 C12 120.0(4) . . ?
C10 C11 C22 116.3(3) . . ?
C12 C11 C22 123.1(3) . . ?
C8 C12 C11 114.8(3) . . ?
C8 C12 C13 116.3(3) . . ?
C13 C12 C11 128.7(3) . . ?
C5 C13 C12 118.5(3) . . ?
C14 C13 C5 114.8(3) . . ?
C14 C13 C12 126.6(3) . . ?
C2 C14 C13 119.9(4) . . ?
C2 C14 C15 106.5(3) . . ?
C13 C14 C15 132.8(3) . . ?
C1 C15 H15 110.2 . . ?
C14 C15 C1 100.8(3) . . ?
C14 C15 H15 110.2 . . ?
C14 C15 C16 114.9(3) . . ?
C16 C15 C1 110.2(3) . . ?
C16 C15 H15 110.2 . . ?
C17 C16 C15 121.8(3) . . ?
C21 C16 C15 119.2(3) . . ?
C21 C16 C17 118.8(3) . . ?
C16 C17 H17 119.9 . . ?
C18 C17 C16 120.2(4) . . ?
C18 C17 H17 119.9 . . ?
C17 C18 H18 119.8 . . ?
C19 C18 C17 120.4(4) . . ?
C19 C18 H18 119.8 . . ?
C18 C19 H19 120.3 . . ?
C20 C19 C18 119.4(4) . . ?
C20 C19 H19 120.3 . . ?
C19 C20 H20 119.5 . . ?
C19 C20 C21 121.1(4) . . ?
C21 C20 H20 119.5 . . ?
C16 C21 H21 119.9 . . ?
C20 C21 C16 120.1(4) . . ?
C20 C21 H21 119.9 . . ?
C23 C22 C11 121.0(3) . . ?
C27 C22 C11 120.0(3) . . ?
C27 C22 C23 118.8(4) . . ?
C22 C23 H23 120.0 . . ?
C24 C23 C22 119.9(4) . . ?
C24 C23 H23 120.0 . . ?
C23 C24 H24 119.4 . . ?
C25 C24 C23 121.2(4) . . ?
C25 C24 H24 119.4 . . ?
C24 C25 H25 120.4 . . ?
C24 C25 C26 119.3(4) . . ?
C26 C25 H25 120.4 . . ?
C25 C26 H26 119.8 . . ?
C27 C26 C25 120.3(4) . . ?
C27 C26 H26 119.8 . . ?
C22 C27 H27 119.8 . . ?
C26 C27 C22 120.5(4) . . ?
C26 C27 H27 119.8 . . ?

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 C15 C14 17.6(4) . . . . ?
O1 C1 C15 C16 -104.1(3) . . . . ?
O1 C2 C3 C4 -170.7(4) . . . . ?
O1 C2 C14 C13 175.7(3) . . . . ?
O1 C2 C14 C15 5.0(4) . . . . ?
O2 C8 C12 C11 12.2(5) . . . . ?
O2 C8 C12 C13 -172.1(3) . . . . ?
O2 C9 C10 C11 6.0(6) . . . . ?
O3 C9 C10 C11 -178.9(4) . . . . ?
O4 N1 C1 O1 -18.7(5) . . . . ?
O4 N1 C1 C15 99.6(5) . . . . ?
O5 N1 C1 O1 161.9(4) . . . . ?
O5 N1 C1 C15 -79.9(5) . . . . ?
N1 C1 C15 C14 -100.6(4) . . . . ?
N1 C1 C15 C16 137.6(3) . . . . ?
C1 O1 C2 C3 -177.8(4) . . . . ?
C1 O1 C2 C14 6.8(4) . . . . ?
C1 C15 C16 C17 85.8(4) . . . . ?
C1 C15 C16 C21 -88.9(4) . . . . ?
C2 O1 C1 N1 103.3(3) . . . . ?
C2 O1 C1 C15 -15.5(4) . . . . ?
C2 C3 C4 C5 -2.7(6) . . . . ?
C2 C14 C15 C1 -13.2(3) . . . . ?
C2 C14 C15 C16 105.3(3) . . . . ?
C3 C2 C14 C13 0.6(6) . . . . ?
C3 C2 C14 C15 -170.1(4) . . . . ?
C3 C4 C5 C6 173.8(4) . . . . ?
C3 C4 C5 C13 -3.1(6) . . . . ?
C4 C5 C6 C7 -174.3(4) . . . . ?
C4 C5 C13 C12 -175.6(3) . . . . ?
C4 C5 C13 C14 7.5(5) . . . . ?
C5 C6 C7 C8 -6.2(7) . . . . ?
C5 C13 C14 C2 -6.2(5) . . . . ?
C5 C13 C14 C15 161.6(3) . . . . ?
C6 C5 C13 C12 7.6(5) . . . . ?
C6 C5 C13 C14 -169.4(3) . . . . ?
C6 C7 C8 O2 -178.3(4) . . . . ?
C6 C7 C8 C12 -0.7(6) . . . . ?
C7 C8 C12 C11 -165.1(4) . . . . ?
C7 C8 C12 C13 10.6(6) . . . . ?
C8 O2 C9 O3 176.3(4) . . . . ?
C8 O2 C9 C10 -8.1(6) . . . . ?
C8 C12 C13 C5 -13.6(5) . . . . ?
C8 C12 C13 C14 163.0(3) . . . . ?
C9 O2 C8 C7 176.3(4) . . . . ?
C9 O2 C8 C12 -1.3(6) . . . . ?
C9 C10 C11 C12 5.1(6) . . . . ?
C9 C10 C11 C22 -165.9(4) . . . . ?
C10 C11 C12 C8 -13.9(5) . . . . ?
C10 C11 C12 C13 171.0(3) . . . . ?
C10 C11 C22 C23 -48.1(5) . . . . ?
C10 C11 C22 C27 127.6(4) . . . . ?
C11 C12 C13 C5 161.4(3) . . . . ?
C11 C12 C13 C14 -22.0(5) . . . . ?
C11 C22 C23 C24 178.1(3) . . . . ?
C11 C22 C27 C26 -176.6(3) . . . . ?
C12 C11 C22 C23 141.1(3) . . . . ?
C12 C11 C22 C27 -43.2(5) . . . . ?
C12 C13 C14 C2 177.1(3) . . . . ?
C12 C13 C14 C15 -15.1(6) . . . . ?
C13 C5 C6 C7 2.6(6) . . . . ?
C13 C14 C15 C1 177.8(4) . . . . ?
C13 C14 C15 C16 -63.7(5) . . . . ?
C14 C2 C3 C4 4.1(6) . . . . ?
C14 C15 C16 C17 -27.2(4) . . . . ?
C14 C15 C16 C21 158.1(3) . . . . ?
C15 C16 C17 C18 -172.9(4) . . . . ?
C15 C16 C21 C20 173.4(4) . . . . ?
C16 C17 C18 C19 -0.4(6) . . . . ?
C17 C16 C21 C20 -1.4(6) . . . . ?
C17 C18 C19 C20 -1.4(7) . . . . ?
C18 C19 C20 C21 1.8(7) . . . . ?
C19 C20 C21 C16 -0.4(7) . . . . ?
C21 C16 C17 C18 1.8(6) . . . . ?
C22 C11 C12 C8 156.5(3) . . . . ?
C22 C11 C12 C13 -18.5(5) . . . . ?
C22 C23 C24 C25 -2.1(6) . . . . ?
C23 C22 C27 C26 -0.8(5) . . . . ?
C23 C24 C25 C26 0.3(6) . . . . ?
C24 C25 C26 C27 1.3(6) . . . . ?
C25 C26 C27 C22 -1.0(6) . . . . ?
C27 C22 C23 C24 2.3(5) . . . . ?

_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 2.283
_oxdiff_exptl_absorpt_empirical_full_min 0.630
####################################################################### 
# 
# 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_ag3021
_database_code_depnum_ccdc_archive 'CCDC 2263638'
loop_
_audit_author_name
_audit_author_address
'Michel Giorgi'
;University of Aix Marseille
France
;
_audit_update_record             
;
2023-05-17 deposited with the CCDC.	2024-04-19 downloaded from the CCDC.
;
_audit_creation_date             2022-05-16
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C27 H20 N2 O3'
_chemical_formula_sum            'C27 H20 N2 O3'
_chemical_formula_weight         420.45
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         'c27 h20 n2 o3'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   9.18760(10)
_cell_length_b                   11.14520(10)
_cell_length_c                   20.9565(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2145.90(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    15399
_cell_measurement_temperature    295
_cell_measurement_theta_max      75.9430
_cell_measurement_theta_min      4.1930
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.689
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.75390
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.51a (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    1.301
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             880
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.24
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0260
_diffrn_reflns_av_unetI/netI     0.0188
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            22277
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.183
_diffrn_reflns_theta_min         4.219
_diffrn_ambient_temperature      295
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3048
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -118.00 -10.00   1.00    1.00    --  -40.91 -27.00  94.00  108
  2  ω    -87.00   7.00   1.00    1.00    --  -40.91 114.00 102.00   94
  3  ω      4.00  83.00   1.00    1.00    --   40.91-101.00 -88.00   79
  4  ω     10.00 118.00   1.00    1.00    --   40.91  27.00-103.00  108
  5  ω    100.00 178.00   1.00   10.00    --  112.00 114.00 102.00   78
  6  ω     32.00 111.00   1.00   10.00    --  112.00-101.00 -88.00   79
  7  ω     35.00 143.00   1.00   10.00    --  112.00 -27.00  94.00  108
  8  ω    101.00 178.00   1.00   10.00    --  112.00 101.00  15.00   77
  9  ω     36.00 112.00   1.00   10.00    --  112.00-114.00  11.00   76
 10  ω     23.00  97.00   1.00    1.00    --   40.91-125.00-150.00   74
 11  ω     39.00 138.00   1.00   10.00    --  112.00 -45.00-120.00   99
 12  ω     56.00 107.00   1.00   10.00    --  112.00-111.00 -60.00   51
 13  ω    115.00 147.00   1.00   10.00    --  112.00  15.00   0.00   32
 14  ω     60.00  86.00   1.00   10.00    --  112.00-111.00-120.00   26
 15  ω     97.00 126.00   1.00   10.00    --  112.00 -61.00-150.00   29
 16  ω     60.00  87.00   1.00   10.00    --  112.00  15.00   0.00   27
 17  ω    103.00 177.00   1.00   10.00    --  112.00 111.00 -60.00   74
 18  ω     41.00  92.00   1.00   10.00    --  112.00-111.00  30.00   51
 19  ω     37.00 107.00   1.00   10.00    --  112.00-111.00 -90.00   70
 20  ω     37.00 139.00   1.00   10.00    --  112.00 -30.00-150.00  102
 21  ω    129.00 168.00   1.00   10.00    --  112.00  27.00-103.00   39
 22  ω     31.00  56.00   1.00   10.00    --  112.00 -94.00  30.00   25
 23  ω     76.00 106.00   1.00   10.00    --  112.00 -94.00  30.00   30
 24  ω     66.00  92.00   1.00   10.00    --  112.00 178.00 120.00   26
 25  ω    125.00 150.00   1.00   10.00    --  112.00 178.00 120.00   25
 26  ω    108.00 134.00   1.00   10.00    --  112.00  56.00 -10.39   26
 27  ω    136.00 162.00   1.00   10.00    --  112.00  56.00 -10.39   26
 28  ω     84.00 116.00   1.00   10.00    --  112.00  61.00 -25.89   32
 29  ω     85.00 111.00   1.00   10.00    --  112.00 -77.00 -90.00   26
 30  ω    109.00 135.00   1.00   10.00    --  112.00 111.00 -90.00   26
 31  ω     97.00 123.00   1.00   10.00    --  112.00  45.00-120.00   26
 32  ω     85.00 111.00   1.00   10.00    --  112.00  27.00-103.00   26
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0617727000
_diffrn_orient_matrix_UB_12      -0.1065619000
_diffrn_orient_matrix_UB_13      0.0382010000
_diffrn_orient_matrix_UB_21      0.0066172000
_diffrn_orient_matrix_UB_22      0.0754436000
_diffrn_orient_matrix_UB_23      0.0615336000
_diffrn_orient_matrix_UB_31      -0.1557187000
_diffrn_orient_matrix_UB_32      0.0454564000
_diffrn_orient_matrix_UB_33      -0.0125718000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.748
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.990
_reflns_number_gt                4332
_reflns_number_total             4452
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.51a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.51a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.51a (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         0.140
_refine_diff_density_min         -0.174
_refine_diff_density_rms         0.033
_refine_ls_abs_structure_details 
;
 Flack x determined using 1836 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.06(8)
_refine_ls_extinction_coef       0.0015(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   1.069
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     291
_refine_ls_number_reflns         4452
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0419
_refine_ls_R_factor_gt           0.0404
_refine_ls_restrained_S_all      1.069
_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)+(0.0769P)²+0.1124P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1123
_refine_ls_wR_factor_ref         0.1142
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1), C2(H2)
2.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C7(H7), C8(H8), C10(H10), C16(H16), C17(H17), C18(H18),
 C19(H19), C20(H20), C22(H22), C23(H23), C24(H24), C25(H25), C26(H26)
2.c Idealised Me refined as rotating group:
 C27(H27A,H27B,H27C)
;
_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 0.43059(19) 0.58598(16) 0.28274(8) 0.0670(4) Uani 1 1 d . . . . .
O2 O 0.4300(4) 0.7182(3) 0.38458(16) 0.1300(12) Uani 1 1 d . . . . .
O3 O 0.6410(4) 0.7917(2) 0.36428(18) 0.1229(11) Uani 1 1 d . . . . .
N1 N 0.8038(2) 0.12768(16) 0.45252(9) 0.0582(4) Uani 1 1 d . . . . .
N2 N 0.5404(3) 0.7237(2) 0.35394(12) 0.0818(7) Uani 1 1 d . . . . .
C1 C 0.6625(2) 0.53237(16) 0.32483(8) 0.0487(4) Uani 1 1 d . . . . .
H1 H 0.713739 0.558707 0.363373 0.058 Uiso 1 1 calc R U . . .
C2 C 0.5637(3) 0.6341(2) 0.29970(10) 0.0599(5) Uani 1 1 d . . . . .
H2 H 0.608952 0.673717 0.262988 0.072 Uiso 1 1 calc R U . . .
C3 C 0.4204(2) 0.4749(2) 0.31309(9) 0.0564(5) Uani 1 1 d . . . . .
C4 C 0.2944(2) 0.4068(3) 0.31086(11) 0.0678(6) Uani 1 1 d . . . . .
H4 H 0.209633 0.435244 0.291919 0.081 Uiso 1 1 calc R U . . .
C5 C 0.3015(2) 0.2954(2) 0.33803(11) 0.0638(5) Uani 1 1 d . . . . .
H5 H 0.219286 0.246791 0.337179 0.077 Uiso 1 1 calc R U . . .
C6 C 0.4288(2) 0.25168(19) 0.36723(9) 0.0532(4) Uani 1 1 d . . . . .
C7 C 0.4333(3) 0.1290(2) 0.38785(11) 0.0614(5) Uani 1 1 d . . . . .
H7 H 0.350123 0.082131 0.383677 0.074 Uiso 1 1 calc R U . . .
C8 C 0.5542(3) 0.07941(19) 0.41308(11) 0.0605(5) Uani 1 1 d . . . . .
H8 H 0.557907 -0.001726 0.423319 0.073 Uiso 1 1 calc R U . . .
C9 C 0.6750(2) 0.15545(17) 0.42335(9) 0.0510(4) Uani 1 1 d . . . . .
C10 C 0.8848(2) 0.22921(19) 0.45765(11) 0.0560(4) Uani 1 1 d . . . . .
H10 H 0.976315 0.233310 0.476454 0.067 Uiso 1 1 calc R U . . .
C11 C 0.8128(2) 0.32464(17) 0.43128(9) 0.0474(4) Uani 1 1 d . . . . .
C12 C 0.6769(2) 0.27834(16) 0.40740(8) 0.0446(4) Uani 1 1 d . . . . .
C13 C 0.5550(2) 0.32684(16) 0.37295(8) 0.0452(4) Uani 1 1 d . . . . .
C14 C 0.5476(2) 0.44028(17) 0.34186(8) 0.0471(4) Uani 1 1 d . . . . .
C15 C 0.7719(2) 0.4931(2) 0.27410(9) 0.0526(4) Uani 1 1 d . . . . .
C16 C 0.7631(3) 0.3839(3) 0.24357(13) 0.0773(7) Uani 1 1 d . . . . .
H16 H 0.687714 0.331171 0.253092 0.093 Uiso 1 1 calc R U . . .
C17 C 0.8675(5) 0.3526(4) 0.19845(18) 0.1070(12) Uani 1 1 d . . . . .
H17 H 0.862099 0.278312 0.178417 0.128 Uiso 1 1 calc R U . . .
C18 C 0.9778(4) 0.4295(5) 0.18315(17) 0.1081(14) Uani 1 1 d . . . . .
H18 H 1.046873 0.407652 0.152850 0.130 Uiso 1 1 calc R U . . .
C19 C 0.9864(3) 0.5380(4) 0.21232(16) 0.0944(11) Uani 1 1 d . . . . .
H19 H 1.060330 0.591095 0.201371 0.113 Uiso 1 1 calc R U . . .
C20 C 0.8847(3) 0.5701(3) 0.25866(13) 0.0703(6) Uani 1 1 d . . . . .
H20 H 0.892691 0.643681 0.279300 0.084 Uiso 1 1 calc R U . . .
C21 C 0.86462(19) 0.44924(17) 0.43877(9) 0.0463(4) Uani 1 1 d . . . . .
C22 C 0.7850(2) 0.5320(2) 0.47429(10) 0.0571(5) Uani 1 1 d . . . . .
H22 H 0.696507 0.509410 0.492154 0.069 Uiso 1 1 calc R U . . .
C23 C 0.8362(3) 0.6472(2) 0.48323(14) 0.0732(7) Uani 1 1 d . . . . .
H23 H 0.781238 0.701808 0.506534 0.088 Uiso 1 1 calc R U . . .
C24 C 0.9675(3) 0.6818(2) 0.45806(17) 0.0789(8) Uani 1 1 d . . . . .
H24 H 1.001565 0.759515 0.464215 0.095 Uiso 1 1 calc R U . . .
C25 C 1.0478(3) 0.6011(2) 0.42389(15) 0.0734(7) Uani 1 1 d . . . . .
H25 H 1.137313 0.623806 0.407030 0.088 Uiso 1 1 calc R U . . .
C26 C 0.9964(2) 0.4851(2) 0.41420(11) 0.0581(5) Uani 1 1 d . . . . .
H26 H 1.052018 0.431096 0.390754 0.070 Uiso 1 1 calc R U . . .
C27 C 0.8434(3) 0.0124(2) 0.48036(15) 0.0757(7) Uani 1 1 d . . . . .
H27A H 0.822090 0.013130 0.525207 0.114 Uiso 1 1 calc R U . . .
H27B H 0.945491 -0.001662 0.474147 0.114 Uiso 1 1 calc R U . . .
H27C H 0.788635 -0.050283 0.460066 0.114 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 C2 1.381(3) . ?
O1 C3 1.395(3) . ?
O2 N2 1.202(4) . ?
O3 N2 1.215(4) . ?
N1 C9 1.367(3) . ?
N1 C10 1.359(3) . ?
N1 C27 1.457(3) . ?
N2 C2 1.528(3) . ?
C1 H1 0.9800 . ?
C1 C2 1.545(3) . ?
C1 C14 1.515(3) . ?
C1 C15 1.527(3) . ?
C2 H2 0.9800 . ?
C3 C4 1.386(4) . ?
C3 C14 1.370(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.367(4) . ?
C5 H5 0.9300 . ?
C5 C6 1.407(3) . ?
C6 C7 1.434(3) . ?
C6 C13 1.435(3) . ?
C7 H7 0.9300 . ?
C7 C8 1.349(4) . ?
C8 H8 0.9300 . ?
C8 C9 1.413(3) . ?
C9 C12 1.410(3) . ?
C10 H10 0.9300 . ?
C10 C11 1.369(3) . ?
C11 C12 1.441(3) . ?
C11 C21 1.476(3) . ?
C12 C13 1.438(3) . ?
C13 C14 1.424(3) . ?
C15 C16 1.377(4) . ?
C15 C20 1.384(4) . ?
C16 H16 0.9300 . ?
C16 C17 1.391(4) . ?
C17 H17 0.9300 . ?
C17 C18 1.366(7) . ?
C18 H18 0.9300 . ?
C18 C19 1.357(6) . ?
C19 H19 0.9300 . ?
C19 C20 1.394(4) . ?
C20 H20 0.9300 . ?
C21 C22 1.393(3) . ?
C21 C26 1.376(3) . ?
C22 H22 0.9300 . ?
C22 C23 1.380(4) . ?
C23 H23 0.9300 . ?
C23 C24 1.372(4) . ?
C24 H24 0.9300 . ?
C24 C25 1.366(5) . ?
C25 H25 0.9300 . ?
C25 C26 1.391(3) . ?
C26 H26 0.9300 . ?
C27 H27A 0.9600 . ?
C27 H27B 0.9600 . ?
C27 H27C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 O1 C3 106.62(16) . . ?
C9 N1 C27 126.5(2) . . ?
C10 N1 C9 108.70(17) . . ?
C10 N1 C27 124.5(2) . . ?
O2 N2 O3 125.4(3) . . ?
O2 N2 C2 118.8(3) . . ?
O3 N2 C2 115.7(3) . . ?
C2 C1 H1 110.1 . . ?
C14 C1 H1 110.1 . . ?
C14 C1 C2 99.67(16) . . ?
C14 C1 C15 115.35(16) . . ?
C15 C1 H1 110.1 . . ?
C15 C1 C2 111.10(15) . . ?
O1 C2 N2 108.7(2) . . ?
O1 C2 C1 108.85(18) . . ?
O1 C2 H2 110.4 . . ?
N2 C2 C1 107.97(18) . . ?
N2 C2 H2 110.4 . . ?
C1 C2 H2 110.4 . . ?
C4 C3 O1 121.79(19) . . ?
C14 C3 O1 113.19(19) . . ?
C14 C3 C4 125.0(2) . . ?
C3 C4 H4 121.8 . . ?
C5 C4 C3 116.3(2) . . ?
C5 C4 H4 121.8 . . ?
C4 C5 H5 118.8 . . ?
C4 C5 C6 122.4(2) . . ?
C6 C5 H5 118.8 . . ?
C5 C6 C7 119.0(2) . . ?
C5 C6 C13 120.4(2) . . ?
C7 C6 C13 120.53(19) . . ?
C6 C7 H7 118.9 . . ?
C8 C7 C6 122.17(19) . . ?
C8 C7 H7 118.9 . . ?
C7 C8 H8 121.3 . . ?
C7 C8 C9 117.44(19) . . ?
C9 C8 H8 121.3 . . ?
N1 C9 C8 127.74(19) . . ?
N1 C9 C12 108.39(17) . . ?
C12 C9 C8 123.8(2) . . ?
N1 C10 H10 124.7 . . ?
N1 C10 C11 110.53(19) . . ?
C11 C10 H10 124.7 . . ?
C10 C11 C12 106.29(17) . . ?
C10 C11 C21 122.15(18) . . ?
C12 C11 C21 130.80(16) . . ?
C9 C12 C11 106.03(17) . . ?
C9 C12 C13 118.33(18) . . ?
C13 C12 C11 135.63(16) . . ?
C6 C13 C12 116.85(17) . . ?
C14 C13 C6 116.23(18) . . ?
C14 C13 C12 126.88(17) . . ?
C3 C14 C1 107.43(17) . . ?
C3 C14 C13 119.46(19) . . ?
C13 C14 C1 132.56(17) . . ?
C16 C15 C1 122.6(2) . . ?
C16 C15 C20 118.9(2) . . ?
C20 C15 C1 118.5(2) . . ?
C15 C16 H16 120.1 . . ?
C15 C16 C17 119.8(3) . . ?
C17 C16 H16 120.1 . . ?
C16 C17 H17 119.5 . . ?
C18 C17 C16 121.0(4) . . ?
C18 C17 H17 119.5 . . ?
C17 C18 H18 120.1 . . ?
C19 C18 C17 119.7(3) . . ?
C19 C18 H18 120.1 . . ?
C18 C19 H19 119.9 . . ?
C18 C19 C20 120.3(3) . . ?
C20 C19 H19 119.9 . . ?
C15 C20 C19 120.3(3) . . ?
C15 C20 H20 119.8 . . ?
C19 C20 H20 119.8 . . ?
C22 C21 C11 120.69(18) . . ?
C26 C21 C11 121.19(18) . . ?
C26 C21 C22 118.02(19) . . ?
C21 C22 H22 119.7 . . ?
C23 C22 C21 120.6(2) . . ?
C23 C22 H22 119.7 . . ?
C22 C23 H23 119.7 . . ?
C24 C23 C22 120.6(2) . . ?
C24 C23 H23 119.7 . . ?
C23 C24 H24 120.3 . . ?
C25 C24 C23 119.4(2) . . ?
C25 C24 H24 120.3 . . ?
C24 C25 H25 119.8 . . ?
C24 C25 C26 120.3(2) . . ?
C26 C25 H25 119.8 . . ?
C21 C26 C25 121.0(2) . . ?
C21 C26 H26 119.5 . . ?
C25 C26 H26 119.5 . . ?
N1 C27 H27A 109.5 . . ?
N1 C27 H27B 109.5 . . ?
N1 C27 H27C 109.5 . . ?
H27A C27 H27B 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 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 C3 C4 C5 174.88(19) . . . . ?
O1 C3 C14 C1 -5.3(2) . . . . ?
O1 C3 C14 C13 -177.93(15) . . . . ?
O2 N2 C2 O1 19.1(4) . . . . ?
O2 N2 C2 C1 -98.8(3) . . . . ?
O3 N2 C2 O1 -164.5(3) . . . . ?
O3 N2 C2 C1 77.6(3) . . . . ?
N1 C9 C12 C11 -2.4(2) . . . . ?
N1 C9 C12 C13 176.74(16) . . . . ?
N1 C10 C11 C12 -0.5(2) . . . . ?
N1 C10 C11 C21 170.44(18) . . . . ?
C1 C15 C16 C17 -179.0(3) . . . . ?
C1 C15 C20 C19 -179.6(2) . . . . ?
C2 O1 C3 C4 174.2(2) . . . . ?
C2 O1 C3 C14 -8.5(2) . . . . ?
C2 C1 C14 C3 15.08(19) . . . . ?
C2 C1 C14 C13 -173.70(18) . . . . ?
C2 C1 C15 C16 -109.5(3) . . . . ?
C2 C1 C15 C20 71.0(2) . . . . ?
C3 O1 C2 N2 -98.85(19) . . . . ?
C3 O1 C2 C1 18.5(2) . . . . ?
C3 C4 C5 C6 0.5(3) . . . . ?
C4 C3 C14 C1 171.87(19) . . . . ?
C4 C3 C14 C13 -0.7(3) . . . . ?
C4 C5 C6 C7 -172.6(2) . . . . ?
C4 C5 C6 C13 3.9(3) . . . . ?
C5 C6 C7 C8 176.4(2) . . . . ?
C5 C6 C13 C12 175.70(17) . . . . ?
C5 C6 C13 C14 -6.4(3) . . . . ?
C6 C7 C8 C9 4.8(3) . . . . ?
C6 C13 C14 C1 -165.49(18) . . . . ?
C6 C13 C14 C3 4.9(2) . . . . ?
C7 C6 C13 C12 -7.9(3) . . . . ?
C7 C6 C13 C14 170.01(17) . . . . ?
C7 C8 C9 N1 174.6(2) . . . . ?
C7 C8 C9 C12 -1.5(3) . . . . ?
C8 C9 C12 C11 174.36(19) . . . . ?
C8 C9 C12 C13 -6.5(3) . . . . ?
C9 N1 C10 C11 -1.0(3) . . . . ?
C9 C12 C13 C6 10.8(2) . . . . ?
C9 C12 C13 C14 -166.86(17) . . . . ?
C10 N1 C9 C8 -174.5(2) . . . . ?
C10 N1 C9 C12 2.2(2) . . . . ?
C10 C11 C12 C9 1.8(2) . . . . ?
C10 C11 C12 C13 -177.1(2) . . . . ?
C10 C11 C21 C22 -112.7(2) . . . . ?
C10 C11 C21 C26 63.5(3) . . . . ?
C11 C12 C13 C6 -170.38(19) . . . . ?
C11 C12 C13 C14 12.0(3) . . . . ?
C11 C21 C22 C23 177.6(2) . . . . ?
C11 C21 C26 C25 -177.0(2) . . . . ?
C12 C11 C21 C22 55.8(3) . . . . ?
C12 C11 C21 C26 -128.0(2) . . . . ?
C12 C13 C14 C1 12.2(3) . . . . ?
C12 C13 C14 C3 -177.48(17) . . . . ?
C13 C6 C7 C8 -0.1(3) . . . . ?
C14 C1 C2 O1 -20.63(19) . . . . ?
C14 C1 C2 N2 97.3(2) . . . . ?
C14 C1 C15 C16 3.0(3) . . . . ?
C14 C1 C15 C20 -176.52(18) . . . . ?
C14 C3 C4 C5 -2.1(3) . . . . ?
C15 C1 C2 O1 101.5(2) . . . . ?
C15 C1 C2 N2 -140.7(2) . . . . ?
C15 C1 C14 C3 -103.92(18) . . . . ?
C15 C1 C14 C13 67.3(2) . . . . ?
C15 C16 C17 C18 -1.0(6) . . . . ?
C16 C15 C20 C19 0.9(4) . . . . ?
C16 C17 C18 C19 0.1(6) . . . . ?
C17 C18 C19 C20 1.2(5) . . . . ?
C18 C19 C20 C15 -1.7(4) . . . . ?
C20 C15 C16 C17 0.5(4) . . . . ?
C21 C11 C12 C9 -168.1(2) . . . . ?
C21 C11 C12 C13 12.9(3) . . . . ?
C21 C22 C23 C24 -0.9(4) . . . . ?
C22 C21 C26 C25 -0.8(3) . . . . ?
C22 C23 C24 C25 0.0(4) . . . . ?
C23 C24 C25 C26 0.6(4) . . . . ?
C24 C25 C26 C21 -0.2(4) . . . . ?
C26 C21 C22 C23 1.3(3) . . . . ?
C27 N1 C9 C8 -0.9(4) . . . . ?
C27 N1 C9 C12 175.7(2) . . . . ?
C27 N1 C10 C11 -174.7(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 1.468
_oxdiff_exptl_absorpt_empirical_full_min 0.771
####################################################################### 
# 
# 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_eyp2-163
_database_code_depnum_ccdc_archive 'CCDC 2306282'
loop_
_audit_author_name
_audit_author_address
'Michel Giorgi'
;Aix Marseille Universite, CNRS, Centrale Marseille, FSCM, Spectropole, Marseille, France
France
;
_audit_update_record             
;
2023-11-07 deposited with the CCDC.	2024-04-19 downloaded from the CCDC.
;
_audit_creation_date             2023-09-14
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2019/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C27 H16 O3'
_chemical_formula_sum            'C27 H16 O3'
_chemical_formula_weight         388.40
_chemical_melting_point          ?
_chemical_oxdiff_formula         'c27 h16 o3'
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'
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                   10.93381(14)
_cell_length_b                   15.53317(18)
_cell_length_c                   11.17806(14)
_cell_angle_alpha                90
_cell_angle_beta                 92.8746(12)
_cell_angle_gamma                90
_cell_volume                     1896.06(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8351
_cell_measurement_temperature    298
_cell_measurement_theta_max      72.1980
_cell_measurement_theta_min      4.9340
_shelx_estimated_absorpt_T_max   0.920
_shelx_estimated_absorpt_T_min   0.872
_exptl_absorpt_coefficient_mu    0.707
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.85348
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.100a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.361
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             808
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0271
_diffrn_reflns_av_unetI/netI     0.0207
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            14711
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.341
_diffrn_reflns_theta_min         4.878
_diffrn_ambient_temperature      298
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3045
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -56.00  33.00   1.00    1.00    --  -40.57  60.00 -29.00   89
  2  ω   -108.00 -15.00   1.00    1.00    --  -40.57 -60.00-169.00   93
  3  ω     38.00 118.00   1.00    5.00    --  103.49 -60.00-169.00   80
  4  ω     75.00 172.00   1.00    5.00    --  103.49  60.00 -29.00   97
  5  ω     15.00  58.00   1.00    1.00    --   40.57 -99.00  30.00   43
  6  ω     16.00 106.00   1.00    1.00    --   40.57  38.00 120.00   90
  7  ω     39.00  87.00   1.00    1.00    --   40.57-125.00-180.00   48
  8  ω     80.00 177.00   1.00    5.00    --  103.49  30.00 -60.00   97
  9  ω    114.00 175.00   1.00    5.00    --  103.49 111.00-180.00   61
 10  ω     75.00 103.00   1.00    5.00    --  103.49  61.00  30.00   28
 11  ω    140.00 166.00   1.00    5.00    --  103.49  61.00  60.00   26
 12  ω     74.00 157.00   1.00    5.00    --  103.49  61.00  90.00   83
 13  ω     33.00 107.00   1.00    5.00    --  103.49-111.00-150.00   74
 14  ω     87.00 113.00   1.00    5.00    --  103.49  45.00  60.00   26
 15  ω     83.00 133.00   1.00    5.00    --  103.49  30.00 150.00   50
 16  ω    116.00 150.00   1.00    5.00    --  103.49 111.00-150.00   34
 17  ω    106.00 157.00   1.00    5.00    --  103.49  77.00   0.00   51
 18  ω     79.00 131.00   1.00    5.00    --  103.49  45.00  90.00   52
 19  ω    123.00 172.00   1.00    5.00    --  103.49  61.00  30.00   49
 20  ω     80.00 106.00   1.00    5.00    --  103.49  61.00  60.00   26
 21  ω     35.00 100.00   1.00    5.00    --  103.49-111.00  60.00   65
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0224222000
_diffrn_orient_matrix_UB_12      0.0125591000
_diffrn_orient_matrix_UB_13      0.1338245000
_diffrn_orient_matrix_UB_21      0.1006924000
_diffrn_orient_matrix_UB_22      0.0693886000
_diffrn_orient_matrix_UB_23      0.0084164000
_diffrn_orient_matrix_UB_31      -0.0962254000
_diffrn_orient_matrix_UB_32      0.0697671000
_diffrn_orient_matrix_UB_33      -0.0325144000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3365
_reflns_number_total             3710
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.100a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.100a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.100a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.172
_refine_diff_density_min         -0.151
_refine_diff_density_rms         0.029
_refine_ls_extinction_coef       0.0021(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2019/2 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     272
_refine_ls_number_reflns         3710
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0378
_refine_ls_R_factor_gt           0.0347
_refine_ls_restrained_S_all      1.043
_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)+(0.0530P)²+0.2575P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0957
_refine_ls_wR_factor_ref         0.0992
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C8(H8), C11(H11), C12(H12), C14(H14),
 C15(H15), C17(H17), C23(H23), C24(H24), C25(H25), C26(H26), C27(H27)
;
_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 0.37379(11) 0.07306(6) -0.06065(10) 0.0673(3) Uani 1 1 d . . . . .
O2 O 0.31528(9) 0.19706(6) -0.14143(8) 0.0526(2) Uani 1 1 d . . . . .
O3 O 0.11570(9) 0.56017(5) 0.19780(9) 0.0545(2) Uani 1 1 d . . . . .
C1 C 0.41145(9) 0.32907(7) 0.17914(9) 0.0371(2) Uani 1 1 d . . . . .
C2 C 0.42676(12) 0.29232(8) 0.29201(11) 0.0492(3) Uani 1 1 d . . . . .
H2 H 0.394970 0.237935 0.306121 0.059 Uiso 1 1 calc R U . . .
C3 C 0.48919(16) 0.33640(11) 0.38363(14) 0.0700(4) Uani 1 1 d . . . . .
H3 H 0.497074 0.312115 0.459673 0.084 Uiso 1 1 calc R U . . .
C4 C 0.53993(15) 0.41616(11) 0.36319(16) 0.0718(5) Uani 1 1 d . . . . .
H4 H 0.582379 0.445277 0.424983 0.086 Uiso 1 1 calc R U . . .
C5 C 0.52727(12) 0.45239(9) 0.25058(15) 0.0604(4) Uani 1 1 d . . . . .
H5 H 0.562363 0.505679 0.236106 0.072 Uiso 1 1 calc R U . . .
C6 C 0.46254(11) 0.40970(7) 0.15912(12) 0.0459(3) Uani 1 1 d . . . . .
H6 H 0.453039 0.434955 0.083787 0.055 Uiso 1 1 calc R U . . .
C7 C 0.35319(9) 0.27985(7) 0.07743(9) 0.0362(2) Uani 1 1 d . . . . .
C8 C 0.38641(11) 0.19659(7) 0.06383(10) 0.0431(3) Uani 1 1 d . . . . .
H8 H 0.429439 0.169122 0.126753 0.052 Uiso 1 1 calc R U . . .
C9 C 0.35758(12) 0.14901(8) -0.04448(11) 0.0488(3) Uani 1 1 d . . . . .
C10 C 0.27705(11) 0.28040(8) -0.12870(10) 0.0448(3) Uani 1 1 d . . . . .
C11 C 0.24011(13) 0.32275(10) -0.23572(11) 0.0572(3) Uani 1 1 d . . . . .
H11 H 0.239069 0.293622 -0.308460 0.069 Uiso 1 1 calc R U . . .
C12 C 0.20609(13) 0.40649(9) -0.23148(11) 0.0558(3) Uani 1 1 d . . . . .
H12 H 0.190040 0.436370 -0.302640 0.067 Uiso 1 1 calc R U . . .
C13 C 0.19445(11) 0.44953(8) -0.12082(10) 0.0464(3) Uani 1 1 d . . . . .
C14 C 0.15728(12) 0.53753(9) -0.11949(13) 0.0548(3) Uani 1 1 d . . . . .
H14 H 0.145688 0.566903 -0.191663 0.066 Uiso 1 1 calc R U . . .
C15 C 0.13845(12) 0.57941(8) -0.01563(14) 0.0545(3) Uani 1 1 d . . . . .
H15 H 0.120157 0.637856 -0.014150 0.065 Uiso 1 1 calc R U . . .
C16 C 0.14790(11) 0.53041(7) 0.08870(11) 0.0457(3) Uani 1 1 d . . . . .
C17 C 0.11903(12) 0.48987(8) 0.27154(12) 0.0492(3) Uani 1 1 d . . . . .
H17 H 0.098730 0.491679 0.351303 0.059 Uiso 1 1 calc R U . . .
C18 C 0.15491(10) 0.41758(7) 0.21623(10) 0.0387(2) Uani 1 1 d . . . . .
C19 C 0.18006(9) 0.44385(7) 0.09491(10) 0.0377(2) Uani 1 1 d . . . . .
C20 C 0.21926(10) 0.40362(7) -0.01180(10) 0.0381(2) Uani 1 1 d . . . . .
C21 C 0.27906(10) 0.32103(7) -0.01813(9) 0.0377(2) Uani 1 1 d . . . . .
C22 C 0.14051(9) 0.33110(7) 0.26714(9) 0.0372(2) Uani 1 1 d . . . . .
C23 C 0.10185(10) 0.26279(7) 0.19430(10) 0.0421(3) Uani 1 1 d . . . . .
H23 H 0.088047 0.271934 0.112513 0.050 Uiso 1 1 calc R U . . .
C24 C 0.08347(12) 0.18167(8) 0.24063(12) 0.0516(3) Uani 1 1 d . . . . .
H24 H 0.059137 0.136652 0.190018 0.062 Uiso 1 1 calc R U . . .
C25 C 0.10128(13) 0.16747(8) 0.36226(12) 0.0544(3) Uani 1 1 d . . . . .
H25 H 0.089873 0.112823 0.393805 0.065 Uiso 1 1 calc R U . . .
C26 C 0.13593(12) 0.23467(9) 0.43621(11) 0.0531(3) Uani 1 1 d . . . . .
H26 H 0.145859 0.225556 0.518350 0.064 Uiso 1 1 calc R U . . .
C27 C 0.15626(11) 0.31573(8) 0.39006(10) 0.0466(3) Uani 1 1 d . . . . .
H27 H 0.180624 0.360388 0.441301 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 C9 1.2080(15) . ?
O2 C9 1.3767(16) . ?
O2 C10 1.3700(15) . ?
O3 C16 1.3667(16) . ?
O3 C17 1.3676(15) . ?
C1 C2 1.3873(16) . ?
C1 C6 1.3941(16) . ?
C1 C7 1.4866(14) . ?
C2 H2 0.9300 . ?
C2 C3 1.3833(19) . ?
C3 H3 0.9300 . ?
C3 C4 1.381(2) . ?
C4 H4 0.9300 . ?
C4 C5 1.379(2) . ?
C5 H5 0.9300 . ?
C5 C6 1.3832(18) . ?
C6 H6 0.9300 . ?
C7 C8 1.3539(16) . ?
C7 C21 1.4561(15) . ?
C8 H8 0.9300 . ?
C8 C9 1.4398(16) . ?
C10 C11 1.4066(18) . ?
C10 C21 1.3870(15) . ?
C11 H11 0.9300 . ?
C11 C12 1.354(2) . ?
C12 H12 0.9300 . ?
C12 C13 1.4174(19) . ?
C13 C14 1.4264(19) . ?
C13 C20 1.4261(15) . ?
C14 H14 0.9300 . ?
C14 C15 1.355(2) . ?
C15 H15 0.9300 . ?
C15 C16 1.3920(18) . ?
C16 C19 1.3907(16) . ?
C17 H17 0.9300 . ?
C17 C18 1.3495(16) . ?
C18 C19 1.4555(15) . ?
C18 C22 1.4705(15) . ?
C19 C20 1.4312(16) . ?
C20 C21 1.4433(16) . ?
C22 C23 1.3903(15) . ?
C22 C27 1.3967(16) . ?
C23 H23 0.9300 . ?
C23 C24 1.3807(16) . ?
C24 H24 0.9300 . ?
C24 C25 1.3815(19) . ?
C25 H25 0.9300 . ?
C25 C26 1.373(2) . ?
C26 H26 0.9300 . ?
C26 C27 1.3830(18) . ?
C27 H27 0.9300 . ?

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 O2 C9 121.51(9) . . ?
C16 O3 C17 105.51(9) . . ?
C2 C1 C6 118.99(11) . . ?
C2 C1 C7 120.76(10) . . ?
C6 C1 C7 119.94(10) . . ?
C1 C2 H2 119.9 . . ?
C3 C2 C1 120.15(13) . . ?
C3 C2 H2 119.9 . . ?
C2 C3 H3 119.7 . . ?
C4 C3 C2 120.59(14) . . ?
C4 C3 H3 119.7 . . ?
C3 C4 H4 120.2 . . ?
C5 C4 C3 119.61(13) . . ?
C5 C4 H4 120.2 . . ?
C4 C5 H5 119.9 . . ?
C4 C5 C6 120.21(13) . . ?
C6 C5 H5 119.9 . . ?
C1 C6 H6 119.8 . . ?
C5 C6 C1 120.42(12) . . ?
C5 C6 H6 119.8 . . ?
C8 C7 C1 118.04(10) . . ?
C8 C7 C21 118.67(10) . . ?
C21 C7 C1 122.44(9) . . ?
C7 C8 H8 118.8 . . ?
C7 C8 C9 122.42(11) . . ?
C9 C8 H8 118.8 . . ?
O1 C9 O2 117.24(11) . . ?
O1 C9 C8 126.84(13) . . ?
O2 C9 C8 115.75(10) . . ?
O2 C10 C11 115.45(11) . . ?
O2 C10 C21 122.09(11) . . ?
C21 C10 C11 122.42(12) . . ?
C10 C11 H11 120.4 . . ?
C12 C11 C10 119.14(12) . . ?
C12 C11 H11 120.4 . . ?
C11 C12 H12 119.3 . . ?
C11 C12 C13 121.36(11) . . ?
C13 C12 H12 119.3 . . ?
C12 C13 C14 119.95(11) . . ?
C12 C13 C20 119.23(11) . . ?
C20 C13 C14 120.82(12) . . ?
C13 C14 H14 119.2 . . ?
C15 C14 C13 121.63(11) . . ?
C15 C14 H14 119.2 . . ?
C14 C15 H15 121.7 . . ?
C14 C15 C16 116.55(12) . . ?
C16 C15 H15 121.7 . . ?
O3 C16 C15 123.44(11) . . ?
O3 C16 C19 110.99(10) . . ?
C19 C16 C15 125.34(12) . . ?
O3 C17 H17 123.6 . . ?
C18 C17 O3 112.82(11) . . ?
C18 C17 H17 123.6 . . ?
C17 C18 C19 105.45(10) . . ?
C17 C18 C22 122.93(10) . . ?
C19 C18 C22 130.21(9) . . ?
C16 C19 C18 104.98(10) . . ?
C16 C19 C20 117.77(10) . . ?
C20 C19 C18 137.11(10) . . ?
C13 C20 C19 116.22(10) . . ?
C13 C20 C21 118.02(10) . . ?
C19 C20 C21 125.75(9) . . ?
C10 C21 C7 115.93(10) . . ?
C10 C21 C20 117.46(10) . . ?
C20 C21 C7 126.26(9) . . ?
C23 C22 C18 120.39(10) . . ?
C23 C22 C27 117.68(10) . . ?
C27 C22 C18 121.77(10) . . ?
C22 C23 H23 119.3 . . ?
C24 C23 C22 121.49(11) . . ?
C24 C23 H23 119.3 . . ?
C23 C24 H24 120.0 . . ?
C23 C24 C25 119.93(12) . . ?
C25 C24 H24 120.0 . . ?
C24 C25 H25 120.3 . . ?
C26 C25 C24 119.48(12) . . ?
C26 C25 H25 120.3 . . ?
C25 C26 H26 119.6 . . ?
C25 C26 C27 120.82(11) . . ?
C27 C26 H26 119.6 . . ?
C22 C27 H27 119.7 . . ?
C26 C27 C22 120.55(11) . . ?
C26 C27 H27 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
O2 C10 C11 C12 -177.15(12) . . . . ?
O2 C10 C21 C7 15.93(16) . . . . ?
O2 C10 C21 C20 -170.48(10) . . . . ?
O3 C16 C19 C18 5.13(12) . . . . ?
O3 C16 C19 C20 -178.41(9) . . . . ?
O3 C17 C18 C19 1.34(14) . . . . ?
O3 C17 C18 C22 -166.35(10) . . . . ?
C1 C2 C3 C4 -1.9(2) . . . . ?
C1 C7 C8 C9 -165.81(10) . . . . ?
C1 C7 C21 C10 151.65(10) . . . . ?
C1 C7 C21 C20 -21.28(16) . . . . ?
C2 C1 C6 C5 -0.12(17) . . . . ?
C2 C1 C7 C8 -43.30(15) . . . . ?
C2 C1 C7 C21 147.39(11) . . . . ?
C2 C3 C4 C5 0.5(2) . . . . ?
C3 C4 C5 C6 1.0(2) . . . . ?
C4 C5 C6 C1 -1.2(2) . . . . ?
C6 C1 C2 C3 1.63(18) . . . . ?
C6 C1 C7 C8 130.20(11) . . . . ?
C6 C1 C7 C21 -39.12(15) . . . . ?
C7 C1 C2 C3 175.19(12) . . . . ?
C7 C1 C6 C5 -173.73(11) . . . . ?
C7 C8 C9 O1 -172.95(13) . . . . ?
C7 C8 C9 O2 11.99(17) . . . . ?
C8 C7 C21 C10 -17.60(15) . . . . ?
C8 C7 C21 C20 169.46(10) . . . . ?
C9 O2 C10 C11 177.90(11) . . . . ?
C9 O2 C10 C21 0.19(17) . . . . ?
C10 O2 C9 O1 170.25(11) . . . . ?
C10 O2 C9 C8 -14.20(16) . . . . ?
C10 C11 C12 C13 -6.8(2) . . . . ?
C11 C10 C21 C7 -161.62(11) . . . . ?
C11 C10 C21 C20 11.96(17) . . . . ?
C11 C12 C13 C14 -179.40(13) . . . . ?
C11 C12 C13 C20 0.09(19) . . . . ?
C12 C13 C14 C15 176.21(12) . . . . ?
C12 C13 C20 C19 -166.52(11) . . . . ?
C12 C13 C20 C21 12.47(16) . . . . ?
C13 C14 C15 C16 -4.85(19) . . . . ?
C13 C20 C21 C7 154.72(10) . . . . ?
C13 C20 C21 C10 -18.12(15) . . . . ?
C14 C13 C20 C19 12.96(16) . . . . ?
C14 C13 C20 C21 -168.05(10) . . . . ?
C14 C15 C16 O3 -170.97(11) . . . . ?
C14 C15 C16 C19 2.97(19) . . . . ?
C15 C16 C19 C18 -169.46(11) . . . . ?
C15 C16 C19 C20 7.00(17) . . . . ?
C16 O3 C17 C18 1.76(14) . . . . ?
C16 C19 C20 C13 -14.41(15) . . . . ?
C16 C19 C20 C21 166.69(10) . . . . ?
C17 O3 C16 C15 170.35(12) . . . . ?
C17 O3 C16 C19 -4.36(13) . . . . ?
C17 C18 C19 C16 -3.83(12) . . . . ?
C17 C18 C19 C20 -179.23(12) . . . . ?
C17 C18 C22 C23 138.40(12) . . . . ?
C17 C18 C22 C27 -36.93(17) . . . . ?
C18 C19 C20 C13 160.57(12) . . . . ?
C18 C19 C20 C21 -18.3(2) . . . . ?
C18 C22 C23 C24 -177.68(11) . . . . ?
C18 C22 C27 C26 176.61(11) . . . . ?
C19 C18 C22 C23 -25.99(17) . . . . ?
C19 C18 C22 C27 158.67(11) . . . . ?
C19 C20 C21 C7 -26.39(17) . . . . ?
C19 C20 C21 C10 160.76(10) . . . . ?
C20 C13 C14 C15 -3.26(19) . . . . ?
C21 C7 C8 C9 3.92(16) . . . . ?
C21 C10 C11 C12 0.6(2) . . . . ?
C22 C18 C19 C16 162.62(11) . . . . ?
C22 C18 C19 C20 -12.8(2) . . . . ?
C22 C23 C24 C25 1.26(19) . . . . ?
C23 C22 C27 C26 1.15(17) . . . . ?
C23 C24 C25 C26 0.7(2) . . . . ?
C24 C25 C26 C27 -1.7(2) . . . . ?
C25 C26 C27 C22 0.75(19) . . . . ?
C27 C22 C23 C24 -2.16(17) . . . . ?

_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 1.352
_oxdiff_exptl_absorpt_empirical_full_min 0.756
