# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_5
_database_code_depnum_ccdc_archive 'CCDC 2253984'
loop_
_audit_author_name
_audit_author_address
'David Cordes'
;University of St Andrews
United Kingdom
;
_audit_update_record             
;
2023-04-04 deposited with the CCDC.	2023-06-01 downloaded from the CCDC.
;
_audit_creation_date             2020-03-05
_audit_creation_method           'by CrystalStructure 4.3'

_chemical_formula_sum            'C25 H19 N3 O4'
_chemical_formula_moiety         'C25 H19 N3 O4'
_chemical_formula_weight         425.44
_chemical_melting_point          ?
_chemical_absolute_configuration ad

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      orthorhombic
_space_group_name_H-M_alt        P212121
_space_group_name_Hall           'P 2ac 2ab'
_space_group_IT_number           19
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 1/2-X,-Y,1/2+Z
3 1/2+X,1/2-Y,-Z
4 -X,1/2+Y,1/2-Z
#------------------------------------------------------------------------------
_cell_length_a                   11.65320(10)
_cell_length_b                   13.39570(11)
_cell_length_c                   14.02840(12)
_cell_angle_alpha                90.0000
_cell_angle_beta                 90.0000
_cell_angle_gamma                90.0000
_cell_volume                     2189.87(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    19791
_cell_measurement_theta_min      3.13
_cell_measurement_theta_max      75.24
_cell_measurement_temperature    125
#------------------------------------------------------------------------------
_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.050
_exptl_crystal_density_diffrn    1.290
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             888.00
_exptl_absorpt_coefficient_mu    0.731
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.8d (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.792
_exptl_absorpt_correction_T_max  0.964

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      125
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 5.811
_diffrn_reflns_number            24536
_diffrn_reflns_av_unetI/netI     0.0087
_diffrn_reflns_av_R_equivalents  0.0190
_diffrn_reflns_theta_max         75.417
_diffrn_reflns_theta_min         4.564
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       16
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             4447
_reflns_number_gt                4432
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.743
_reflns_Friedel_fraction_max     0.961
_reflns_Friedel_fraction_full    0.995

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0302
_refine_ls_R_factor_gt           0.0300
_refine_ls_wR_factor_ref         0.0815
_refine_ls_wR_factor_gt          0.0813
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         4447
_refine_ls_number_parameters     291
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0531P)²+0.3304P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         0.23
_refine_diff_density_min         -0.26
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0109(8)
_refine_ls_abs_structure_details 
;
 Flack x determined using 1869 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.05(5)

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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
N N 0.0311 0.0180
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0492 0.0322
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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 0.70249(11) 0.23479(9) 0.23250(9) 0.0342(3) Uani 1 1 d . . . . .
O2 O 0.79094(11) 0.38232(9) 0.25304(10) 0.0368(3) Uani 1 1 d . . . . .
O3 O 1.14590(15) 0.04762(16) 0.05574(15) 0.0691(5) Uani 1 1 d . . . . .
O4 O 1.07375(13) 0.11604(13) -0.06822(11) 0.0522(4) Uani 1 1 d . . . . .
N5 N 0.37460(16) 0.50245(13) 0.19089(13) 0.0464(4) Uani 1 1 d . . . . .
N6 N 0.62387(15) 0.71609(11) 0.29460(11) 0.0386(4) Uani 1 1 d . . . . .
N10 N 1.07150(12) 0.09662(11) 0.01658(12) 0.0365(4) Uani 1 1 d . . . . .
C1 C 0.71110(14) 0.32860(12) 0.26761(10) 0.0258(3) Uani 1 1 d . . . . .
C2 C 0.60665(13) 0.35289(11) 0.32857(10) 0.0234(3) Uani 1 1 d . . . . .
H2 H 0.535407 0.334003 0.293164 0.028 Uiso 1 1 calc R U . . .
C3 C 0.60378(13) 0.46551(11) 0.35088(10) 0.0230(3) Uani 1 1 d . . . . .
H3 H 0.682149 0.483933 0.373980 0.028 Uiso 1 1 calc R U . . .
C4 C 0.58166(14) 0.52781(12) 0.25843(11) 0.0257(3) Uani 1 1 d . . . . .
H4 H 0.637314 0.505345 0.208594 0.031 Uiso 1 1 calc R U . . .
C5 C 0.46452(16) 0.51470(12) 0.22054(12) 0.0312(4) Uani 1 1 d . . . . .
C6 C 0.60348(15) 0.63416(12) 0.27849(11) 0.0284(3) Uani 1 1 d . . . . .
C7 C 0.79641(14) 0.20063(11) 0.17931(12) 0.0291(3) Uani 1 1 d . . . . .
C8 C 0.89121(18) 0.16290(15) 0.22593(13) 0.0401(4) Uani 1 1 d . . . . .
H8 H 0.893900 0.161305 0.293599 0.048 Uiso 1 1 calc R U . . .
C9 C 0.98226(17) 0.12745(15) 0.17250(14) 0.0402(4) Uani 1 1 d . . . . .
H9 H 1.048389 0.100491 0.202594 0.048 Uiso 1 1 calc R U . . .
C10 C 0.97470(14) 0.13218(11) 0.07408(12) 0.0292(3) Uani 1 1 d . . . . .
C11 C 0.87995(15) 0.16920(13) 0.02720(12) 0.0338(4) Uani 1 1 d . . . . .
H11 H 0.877212 0.171128 -0.040456 0.041 Uiso 1 1 calc R U . . .
C12 C 0.78879(16) 0.20353(14) 0.08138(13) 0.0350(4) Uani 1 1 d . . . . .
H12 H 0.721753 0.228802 0.051340 0.042 Uiso 1 1 calc R U . . .
C13 C 0.61363(13) 0.29248(11) 0.42067(11) 0.0241(3) Uani 1 1 d . . . . .
C14 C 0.53097(15) 0.22274(13) 0.44315(12) 0.0309(3) Uani 1 1 d . . . . .
H14 H 0.471267 0.209092 0.398926 0.037 Uiso 1 1 calc R U . . .
C15 C 0.53372(16) 0.17214(13) 0.52952(13) 0.0354(4) Uani 1 1 d . . . . .
H15 H 0.476060 0.124156 0.543393 0.042 Uiso 1 1 calc R U . . .
C16 C 0.61898(15) 0.19053(12) 0.59550(12) 0.0312(3) Uani 1 1 d . . . . .
C17 C 0.70204(17) 0.25989(15) 0.57252(14) 0.0407(4) Uani 1 1 d . . . . .
H17 H 0.761611 0.273558 0.616866 0.049 Uiso 1 1 calc R U . . .
C18 C 0.70039(15) 0.31014(14) 0.48595(13) 0.0365(4) Uani 1 1 d . . . . .
H18 H 0.759137 0.356908 0.471443 0.044 Uiso 1 1 calc R U . . .
C19 C 0.6221(2) 0.13569(17) 0.68918(14) 0.0451(5) Uani 1 1 d . . . . .
H19A H 0.544217 0.115282 0.706787 0.054 Uiso 1 1 calc R U . . .
H19B H 0.653369 0.179664 0.738613 0.054 Uiso 1 1 calc R U . . .
H19C H 0.670908 0.076423 0.683092 0.054 Uiso 1 1 calc R U . . .
C20 C 0.52061(13) 0.49310(11) 0.42962(10) 0.0232(3) Uani 1 1 d . . . . .
C21 C 0.55723(14) 0.55727(13) 0.50108(11) 0.0297(3) Uani 1 1 d . . . . .
H21 H 0.632926 0.583513 0.499131 0.036 Uiso 1 1 calc R U . . .
C22 C 0.48451(16) 0.58362(14) 0.57545(12) 0.0353(4) Uani 1 1 d . . . . .
H22 H 0.510285 0.628094 0.623658 0.042 Uiso 1 1 calc R U . . .
C23 C 0.37419(15) 0.54483(13) 0.57917(12) 0.0336(4) Uani 1 1 d . . . . .
H23 H 0.324417 0.562356 0.630129 0.040 Uiso 1 1 calc R U . . .
C24 C 0.33675(14) 0.48034(13) 0.50820(12) 0.0309(4) Uani 1 1 d . . . . .
H24 H 0.261303 0.453607 0.510713 0.037 Uiso 1 1 calc R U . . .
C25 C 0.40934(14) 0.45482(12) 0.43356(11) 0.0266(3) Uani 1 1 d . . . . .
H25 H 0.383101 0.411075 0.384916 0.032 Uiso 1 1 calc R U . . .


#==============================================================================
_computing_data_collection       'CrysAlisPro 1.171.39.8d (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.8d (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.8d (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXT Version 2018/2 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL Version 2018/3 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.3 (Rigaku, 2018)'
_computing_molecular_graphics    'CrystalStructure 4.3'

#==============================================================================
# MOLECULAR GEOMETRY

_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 1.354(2) . ?
O1 C7 1.4015(19) . ?
O2 C1 1.194(2) . ?
O3 N10 1.218(2) . ?
O4 N10 1.218(2) . ?
N5 C5 1.139(3) . ?
N6 C6 1.145(2) . ?
N10 C10 1.466(2) . ?
C1 C2 1.523(2) . ?
C2 C13 1.527(2) . ?
C2 C3 1.541(2) . ?
C2 H2 1.0000 . ?
C3 C20 1.515(2) . ?
C3 C4 1.564(2) . ?
C3 H3 1.0000 . ?
C4 C6 1.474(2) . ?
C4 C5 1.475(2) . ?
C4 H4 1.0000 . ?
C7 C12 1.377(2) . ?
C7 C8 1.380(3) . ?
C8 C9 1.383(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.385(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.377(2) . ?
C11 C12 1.385(2) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C13 C14 1.378(2) . ?
C13 C18 1.385(2) . ?
C14 C15 1.389(2) . ?
C14 H14 0.9500 . ?
C15 C16 1.380(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.380(3) . ?
C16 C19 1.506(2) . ?
C17 C18 1.389(3) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 C21 1.388(2) . ?
C20 C25 1.395(2) . ?
C21 C22 1.390(2) . ?
C21 H21 0.9500 . ?
C22 C23 1.388(2) . ?
C22 H22 0.9500 . ?
C23 C24 1.388(2) . ?
C23 H23 0.9500 . ?
C24 C25 1.389(2) . ?
C24 H24 0.9500 . ?
C25 H25 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 C7 116.04(13) . . ?
O4 N10 O3 122.69(17) . . ?
O4 N10 C10 118.97(16) . . ?
O3 N10 C10 118.33(17) . . ?
O2 C1 O1 123.72(14) . . ?
O2 C1 C2 126.18(14) . . ?
O1 C1 C2 110.09(13) . . ?
C1 C2 C13 108.63(12) . . ?
C1 C2 C3 109.91(12) . . ?
C13 C2 C3 110.38(11) . . ?
C1 C2 H2 109.3 . . ?
C13 C2 H2 109.3 . . ?
C3 C2 H2 109.3 . . ?
C20 C3 C2 113.62(12) . . ?
C20 C3 C4 111.65(12) . . ?
C2 C3 C4 110.96(12) . . ?
C20 C3 H3 106.7 . . ?
C2 C3 H3 106.7 . . ?
C4 C3 H3 106.7 . . ?
C6 C4 C5 110.08(14) . . ?
C6 C4 C3 109.21(12) . . ?
C5 C4 C3 112.82(13) . . ?
C6 C4 H4 108.2 . . ?
C5 C4 H4 108.2 . . ?
C3 C4 H4 108.2 . . ?
N5 C5 C4 178.51(19) . . ?
N6 C6 C4 177.91(19) . . ?
C12 C7 C8 122.34(16) . . ?
C12 C7 O1 118.13(16) . . ?
C8 C7 O1 119.50(15) . . ?
C7 C8 C9 118.89(16) . . ?
C7 C8 H8 120.6 . . ?
C9 C8 H8 120.6 . . ?
C8 C9 C10 118.41(17) . . ?
C8 C9 H9 120.8 . . ?
C10 C9 H9 120.8 . . ?
C11 C10 C9 122.92(15) . . ?
C11 C10 N10 118.10(15) . . ?
C9 C10 N10 118.98(16) . . ?
C10 C11 C12 118.19(15) . . ?
C10 C11 H11 120.9 . . ?
C12 C11 H11 120.9 . . ?
C7 C12 C11 119.25(17) . . ?
C7 C12 H12 120.4 . . ?
C11 C12 H12 120.4 . . ?
C14 C13 C18 118.34(14) . . ?
C14 C13 C2 121.04(14) . . ?
C18 C13 C2 120.54(14) . . ?
C13 C14 C15 120.95(16) . . ?
C13 C14 H14 119.5 . . ?
C15 C14 H14 119.5 . . ?
C16 C15 C14 120.97(16) . . ?
C16 C15 H15 119.5 . . ?
C14 C15 H15 119.5 . . ?
C17 C16 C15 117.93(16) . . ?
C17 C16 C19 121.01(17) . . ?
C15 C16 C19 121.05(17) . . ?
C16 C17 C18 121.41(17) . . ?
C16 C17 H17 119.3 . . ?
C18 C17 H17 119.3 . . ?
C13 C18 C17 120.38(16) . . ?
C13 C18 H18 119.8 . . ?
C17 C18 H18 119.8 . . ?
C16 C19 H19A 109.5 . . ?
C16 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C16 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C21 C20 C25 118.99(14) . . ?
C21 C20 C3 118.76(14) . . ?
C25 C20 C3 122.25(13) . . ?
C20 C21 C22 120.81(15) . . ?
C20 C21 H21 119.6 . . ?
C22 C21 H21 119.6 . . ?
C23 C22 C21 119.87(15) . . ?
C23 C22 H22 120.1 . . ?
C21 C22 H22 120.1 . . ?
C22 C23 C24 119.81(15) . . ?
C22 C23 H23 120.1 . . ?
C24 C23 H23 120.1 . . ?
C25 C24 C23 120.16(15) . . ?
C25 C24 H24 119.9 . . ?
C23 C24 H24 119.9 . . ?
C24 C25 C20 120.35(14) . . ?
C24 C25 H25 119.8 . . ?
C20 C25 H25 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
C7 O1 C1 O2 2.4(2) . . . . ?
C7 O1 C1 C2 -176.50(13) . . . . ?
O2 C1 C2 C13 -107.84(18) . . . . ?
O1 C1 C2 C13 70.98(16) . . . . ?
O2 C1 C2 C3 13.0(2) . . . . ?
O1 C1 C2 C3 -168.16(12) . . . . ?
C1 C2 C3 C20 -166.13(12) . . . . ?
C13 C2 C3 C20 -46.33(17) . . . . ?
C1 C2 C3 C4 67.09(16) . . . . ?
C13 C2 C3 C4 -173.11(12) . . . . ?
C20 C3 C4 C6 63.91(17) . . . . ?
C2 C3 C4 C6 -168.23(13) . . . . ?
C20 C3 C4 C5 -58.85(17) . . . . ?
C2 C3 C4 C5 69.01(16) . . . . ?
C1 O1 C7 C12 -99.78(18) . . . . ?
C1 O1 C7 C8 82.1(2) . . . . ?
C12 C7 C8 C9 0.5(3) . . . . ?
O1 C7 C8 C9 178.60(17) . . . . ?
C7 C8 C9 C10 0.6(3) . . . . ?
C8 C9 C10 C11 -1.0(3) . . . . ?
C8 C9 C10 N10 178.84(17) . . . . ?
O4 N10 C10 C11 12.3(2) . . . . ?
O3 N10 C10 C11 -166.85(18) . . . . ?
O4 N10 C10 C9 -167.58(17) . . . . ?
O3 N10 C10 C9 13.3(3) . . . . ?
C9 C10 C11 C12 0.3(3) . . . . ?
N10 C10 C11 C12 -179.51(16) . . . . ?
C8 C7 C12 C11 -1.2(3) . . . . ?
O1 C7 C12 C11 -179.30(15) . . . . ?
C10 C11 C12 C7 0.8(3) . . . . ?
C1 C2 C13 C14 -117.71(16) . . . . ?
C3 C2 C13 C14 121.72(16) . . . . ?
C1 C2 C13 C18 65.53(19) . . . . ?
C3 C2 C13 C18 -55.0(2) . . . . ?
C18 C13 C14 C15 0.7(3) . . . . ?
C2 C13 C14 C15 -176.13(15) . . . . ?
C13 C14 C15 C16 0.3(3) . . . . ?
C14 C15 C16 C17 -0.7(3) . . . . ?
C14 C15 C16 C19 -179.96(18) . . . . ?
C15 C16 C17 C18 0.1(3) . . . . ?
C19 C16 C17 C18 179.40(19) . . . . ?
C14 C13 C18 C17 -1.3(3) . . . . ?
C2 C13 C18 C17 175.59(17) . . . . ?
C16 C17 C18 C13 0.8(3) . . . . ?
C2 C3 C20 C21 133.57(15) . . . . ?
C4 C3 C20 C21 -100.01(16) . . . . ?
C2 C3 C20 C25 -45.28(19) . . . . ?
C4 C3 C20 C25 81.14(17) . . . . ?
C25 C20 C21 C22 -0.2(2) . . . . ?
C3 C20 C21 C22 -179.12(16) . . . . ?
C20 C21 C22 C23 0.6(3) . . . . ?
C21 C22 C23 C24 -0.4(3) . . . . ?
C22 C23 C24 C25 -0.1(3) . . . . ?
C23 C24 C25 C20 0.5(3) . . . . ?
C21 C20 C25 C24 -0.3(2) . . . . ?
C3 C20 C25 C24 178.54(15) . . . . ?


#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.




_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Chloroform/hexane'
####################################################################### 
# 
# 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_14
_database_code_depnum_ccdc_archive 'CCDC 2253985'
loop_
_audit_author_name
_audit_author_address
'David Cordes'
;University of St Andrews
United Kingdom
;
_audit_update_record             
;
2023-04-04 deposited with the CCDC.	2023-06-01 downloaded from the CCDC.
;
_audit_creation_date             2021-05-25
_audit_creation_method           'by CrystalStructure 4.3'


_chemical_formula_sum            'C25 H16 F4 N2 O2'
_chemical_formula_moiety         'C25 H16 F4 N2 O2'
_chemical_formula_weight         452.41
_chemical_melting_point          ?
_chemical_absolute_configuration ad

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      orthorhombic
_space_group_name_H-M_alt        P212121
_space_group_name_Hall           'P 2ac 2ab'
_space_group_IT_number           19
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 1/2-X,-Y,1/2+Z
3 1/2+X,1/2-Y,-Z
4 -X,1/2+Y,1/2-Z
#------------------------------------------------------------------------------
_cell_length_a                   5.87366(8)
_cell_length_b                   9.56529(13)
_cell_length_c                   36.9186(4)
_cell_angle_alpha                90.0000
_cell_angle_beta                 90.0000
_cell_angle_gamma                90.0000
_cell_volume                     2074.21(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    15197
_cell_measurement_theta_min      2.42
_cell_measurement_theta_max      68.04
_cell_measurement_temperature    173
#------------------------------------------------------------------------------
_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.030
_exptl_crystal_density_diffrn    1.449
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             928.00
_exptl_absorpt_coefficient_mu    1.005
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.14a (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.777
_exptl_absorpt_correction_T_max  0.970

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      173
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_measurement_device_type  'Rigaku XtaLAB P100'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 5.811
_diffrn_reflns_number            20708
_diffrn_reflns_av_unetI/netI     0.0199
_diffrn_reflns_av_R_equivalents  0.0287
_diffrn_reflns_theta_max         68.152
_diffrn_reflns_theta_min         4.791
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -44
_diffrn_reflns_limit_l_max       34
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             3758
_reflns_number_gt                3754
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.684
_reflns_Friedel_fraction_max     0.982
_reflns_Friedel_fraction_full    0.991

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0513
_refine_ls_R_factor_gt           0.0513
_refine_ls_wR_factor_ref         0.1079
_refine_ls_wR_factor_gt          0.1078
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         3758
_refine_ls_number_parameters     300
_refine_ls_goodness_of_fit_ref   1.230
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0754P)²+0.1558P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.001
_refine_diff_density_max         0.45
_refine_diff_density_min         -0.54
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.059(3)
_refine_ls_abs_structure_details 
;
 Flack x determined using 1517 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.01(3)

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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
F F 0.0727 0.0534
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
N N 0.0311 0.0180
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0492 0.0322
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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
F8 F 0.0348(3) 0.82595(18) 0.70264(4) 0.0521(4) Uani 1 1 d . . . . .
F9 F 0.0336(3) 0.8581(2) 0.77511(4) 0.0711(5) Uani 1 1 d . . . . .
F11 F 0.7296(4) 1.10108(19) 0.76756(5) 0.0702(6) Uani 1 1 d . . . . .
F12 F 0.7270(3) 1.06982(18) 0.69483(4) 0.0555(4) Uani 1 1 d . . . . .
O1 O 0.6274(3) 0.75487(15) 0.66531(4) 0.0326(4) Uani 1 1 d . . . . .
O7 O 0.3736(3) 0.93242(17) 0.66069(4) 0.0359(4) Uani 1 1 d . . . . .
N5 N 0.6377(4) 0.4647(2) 0.51426(5) 0.0441(5) Uani 1 1 d . . . . .
N6 N 0.0558(3) 0.7182(2) 0.53820(5) 0.0400(5) Uani 1 1 d . . . . .
C1 C 0.5117(3) 0.82771(18) 0.64687(5) 0.0250(4) Uani 1 1 d . . . . .
C2 C 0.4947(3) 0.82919(18) 0.60596(5) 0.0234(4) Uani 1 1 d . . . . .
H2 H 0.334367 0.852411 0.599104 0.028 Uiso 1 1 calc R U . . .
C3 C 0.5543(3) 0.68358(19) 0.59012(4) 0.0235(4) Uani 1 1 d . . . . .
H3 H 0.723080 0.671996 0.592084 0.028 Uiso 1 1 calc R U . . .
C4 C 0.4941(3) 0.6860(2) 0.54882(5) 0.0251(4) Uani 1 1 d . . . . .
H4 H 0.572529 0.768384 0.537778 0.030 Uiso 1 1 calc R U . . .
C5 C 0.5735(4) 0.5598(2) 0.52970(5) 0.0302(5) Uani 1 1 d . . . . .
C6 C 0.2468(4) 0.7027(2) 0.54264(5) 0.0294(5) Uani 1 1 d . . . . .
C7 C 0.3799(4) 0.9478(2) 0.69802(5) 0.0354(5) Uani 1 1 d . . . . .
C8 C 0.2042(4) 0.8956(3) 0.71856(6) 0.0406(5) Uani 1 1 d . . . . .
C9 C 0.2053(5) 0.9130(3) 0.75594(7) 0.0496(7) Uani 1 1 d . . . . .
C10 C 0.3803(6) 0.9831(3) 0.77290(6) 0.0522(7) Uani 1 1 d . . . . .
H10 H 0.380309 0.995673 0.798426 0.063 Uiso 1 1 calc R U . . .
C11 C 0.5545(5) 1.0344(3) 0.75204(7) 0.0492(7) Uani 1 1 d . . . . .
C12 C 0.5554(5) 1.0187(3) 0.71476(6) 0.0419(6) Uani 1 1 d . . . . .
C13 C 0.6503(3) 0.94486(19) 0.59189(5) 0.0244(4) Uani 1 1 d . . . . .
C14 C 0.8619(3) 0.96975(19) 0.60776(5) 0.0270(4) Uani 1 1 d . . . . .
H14 H 0.911983 0.912718 0.627259 0.032 Uiso 1 1 calc R U . . .
C15 C 1.0001(3) 1.07748(19) 0.59524(5) 0.0284(4) Uani 1 1 d . . . . .
H15 H 1.142594 1.093934 0.606639 0.034 Uiso 1 1 calc R U . . .
C16 C 0.9338(3) 1.16176(19) 0.56632(5) 0.0278(4) Uani 1 1 d . . . . .
C17 C 0.7240(4) 1.1349(2) 0.55034(5) 0.0304(4) Uani 1 1 d . . . . .
H17 H 0.676529 1.189938 0.530293 0.036 Uiso 1 1 calc R U . . .
C18 C 0.5821(3) 1.02953(19) 0.56303(5) 0.0282(4) Uani 1 1 d . . . . .
H18 H 0.437907 1.014947 0.552018 0.034 Uiso 1 1 calc R U . . .
C19 C 1.0845(4) 1.2784(2) 0.55310(6) 0.0332(5) Uani 1 1 d . . . . .
H19A H 1.212202 1.239090 0.539392 0.040 Uiso 1 1 calc R U . . .
H19B H 1.142950 1.331051 0.573887 0.040 Uiso 1 1 calc R U . . .
H19C H 0.996401 1.340943 0.537434 0.040 Uiso 1 1 calc R U . . .
C20 C 0.4455(3) 0.56132(19) 0.61003(5) 0.0262(4) Uani 1 1 d . . . . .
C21 C 0.2321(4) 0.5714(2) 0.62628(5) 0.0313(5) Uani 1 1 d . . . . .
H21 H 0.144220 0.654056 0.623435 0.038 Uiso 1 1 calc R U . . .
C22 C 0.1472(4) 0.4606(3) 0.64668(6) 0.0390(5) Uani 1 1 d . . . . .
H22 H 0.003216 0.469041 0.658199 0.047 Uiso 1 1 calc R U . . .
C23 C 0.2711(5) 0.3380(2) 0.65031(6) 0.0431(6) Uani 1 1 d . . . . .
H23 H 0.213034 0.262909 0.664397 0.052 Uiso 1 1 calc R U . . .
C24 C 0.4815(5) 0.3256(2) 0.63314(6) 0.0407(5) Uani 1 1 d . . . . .
H24 H 0.566053 0.241309 0.635050 0.049 Uiso 1 1 calc R U . . .
C25 C 0.5669(4) 0.4368(2) 0.61326(5) 0.0321(5) Uani 1 1 d . . . . .
H25 H 0.710496 0.427986 0.601656 0.039 Uiso 1 1 calc R U . . .


#==============================================================================
_computing_data_collection       'CrysAlisPro 1.171.40.14a (Rigaku OD, 2018)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.14a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.14a (Rigaku OD, 2018)'
_computing_structure_solution    'SIR2011 (Burla, et al., 2012)'
_computing_structure_refinement  'SHELXL Version 2018/3 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.3 (Rigaku, 2019)'
_computing_molecular_graphics    'CrystalStructure 4.3'

#==============================================================================
# MOLECULAR GEOMETRY

_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
F8 C8 1.334(3) . ?
F9 C9 1.339(3) . ?
F11 C11 1.339(3) . ?
F12 C12 1.340(3) . ?
O1 C1 1.188(2) . ?
O7 C1 1.386(2) . ?
O7 C7 1.386(2) . ?
N5 C5 1.138(3) . ?
N6 C6 1.143(3) . ?
C1 C2 1.514(2) . ?
C2 C13 1.526(3) . ?
C2 C3 1.551(2) . ?
C2 H2 1.0000 . ?
C3 C20 1.522(2) . ?
C3 C4 1.565(2) . ?
C3 H3 1.0000 . ?
C4 C5 1.474(3) . ?
C4 C6 1.479(3) . ?
C4 H4 1.0000 . ?
C7 C8 1.375(4) . ?
C7 C12 1.380(4) . ?
C8 C9 1.390(3) . ?
C9 C10 1.378(5) . ?
C10 C11 1.371(5) . ?
C10 H10 0.9500 . ?
C11 C12 1.385(4) . ?
C13 C14 1.394(3) . ?
C13 C18 1.397(3) . ?
C14 C15 1.391(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.394(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.390(3) . ?
C16 C19 1.505(3) . ?
C17 C18 1.389(3) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 C25 1.393(3) . ?
C20 C21 1.393(3) . ?
C21 C22 1.393(3) . ?
C21 H21 0.9500 . ?
C22 C23 1.387(4) . ?
C22 H22 0.9500 . ?
C23 C24 1.394(4) . ?
C23 H23 0.9500 . ?
C24 C25 1.386(3) . ?
C24 H24 0.9500 . ?
C25 H25 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O7 C7 115.28(15) . . ?
O1 C1 O7 123.21(17) . . ?
O1 C1 C2 127.95(17) . . ?
O7 C1 C2 108.79(15) . . ?
C1 C2 C13 107.87(14) . . ?
C1 C2 C3 110.67(14) . . ?
C13 C2 C3 112.79(15) . . ?
C1 C2 H2 108.5 . . ?
C13 C2 H2 108.5 . . ?
C3 C2 H2 108.5 . . ?
C20 C3 C2 114.40(14) . . ?
C20 C3 C4 112.75(14) . . ?
C2 C3 C4 107.65(14) . . ?
C20 C3 H3 107.2 . . ?
C2 C3 H3 107.2 . . ?
C4 C3 H3 107.2 . . ?
C5 C4 C6 108.98(17) . . ?
C5 C4 C3 112.54(15) . . ?
C6 C4 C3 111.94(15) . . ?
C5 C4 H4 107.7 . . ?
C6 C4 H4 107.7 . . ?
C3 C4 H4 107.7 . . ?
N5 C5 C4 178.1(2) . . ?
N6 C6 C4 178.6(3) . . ?
C8 C7 C12 119.5(2) . . ?
C8 C7 O7 119.3(2) . . ?
C12 C7 O7 121.2(2) . . ?
F8 C8 C7 119.9(2) . . ?
F8 C8 C9 120.0(2) . . ?
C7 C8 C9 120.1(2) . . ?
F9 C9 C10 120.8(2) . . ?
F9 C9 C8 118.3(3) . . ?
C10 C9 C8 120.8(3) . . ?
C11 C10 C9 118.4(2) . . ?
C11 C10 H10 120.8 . . ?
C9 C10 H10 120.8 . . ?
F11 C11 C10 120.2(2) . . ?
F11 C11 C12 118.3(3) . . ?
C10 C11 C12 121.5(2) . . ?
F12 C12 C7 119.7(2) . . ?
F12 C12 C11 120.6(2) . . ?
C7 C12 C11 119.7(2) . . ?
C14 C13 C18 118.49(18) . . ?
C14 C13 C2 120.97(16) . . ?
C18 C13 C2 120.54(17) . . ?
C15 C14 C13 120.47(17) . . ?
C15 C14 H14 119.8 . . ?
C13 C14 H14 119.8 . . ?
C14 C15 C16 121.34(18) . . ?
C14 C15 H15 119.3 . . ?
C16 C15 H15 119.3 . . ?
C17 C16 C15 117.79(18) . . ?
C17 C16 C19 121.38(18) . . ?
C15 C16 C19 120.84(18) . . ?
C18 C17 C16 121.50(19) . . ?
C18 C17 H17 119.2 . . ?
C16 C17 H17 119.2 . . ?
C17 C18 C13 120.40(19) . . ?
C17 C18 H18 119.8 . . ?
C13 C18 H18 119.8 . . ?
C16 C19 H19A 109.5 . . ?
C16 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C16 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C25 C20 C21 118.86(18) . . ?
C25 C20 C3 118.90(18) . . ?
C21 C20 C3 122.19(18) . . ?
C22 C21 C20 120.2(2) . . ?
C22 C21 H21 119.9 . . ?
C20 C21 H21 119.9 . . ?
C23 C22 C21 120.5(2) . . ?
C23 C22 H22 119.7 . . ?
C21 C22 H22 119.7 . . ?
C22 C23 C24 119.5(2) . . ?
C22 C23 H23 120.2 . . ?
C24 C23 H23 120.2 . . ?
C25 C24 C23 119.8(2) . . ?
C25 C24 H24 120.1 . . ?
C23 C24 H24 120.1 . . ?
C24 C25 C20 121.1(2) . . ?
C24 C25 H25 119.5 . . ?
C20 C25 H25 119.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C7 O7 C1 O1 0.4(3) . . . . ?
C7 O7 C1 C2 -177.19(17) . . . . ?
O1 C1 C2 C13 -96.8(2) . . . . ?
O7 C1 C2 C13 80.62(19) . . . . ?
O1 C1 C2 C3 27.0(3) . . . . ?
O7 C1 C2 C3 -155.55(16) . . . . ?
C1 C2 C3 C20 44.6(2) . . . . ?
C13 C2 C3 C20 165.50(15) . . . . ?
C1 C2 C3 C4 170.70(14) . . . . ?
C13 C2 C3 C4 -68.35(19) . . . . ?
C20 C3 C4 C5 -61.0(2) . . . . ?
C2 C3 C4 C5 171.89(16) . . . . ?
C20 C3 C4 C6 62.2(2) . . . . ?
C2 C3 C4 C6 -65.0(2) . . . . ?
C1 O7 C7 C8 -102.5(2) . . . . ?
C1 O7 C7 C12 79.7(3) . . . . ?
C12 C7 C8 F8 -179.5(2) . . . . ?
O7 C7 C8 F8 2.8(3) . . . . ?
C12 C7 C8 C9 -0.7(4) . . . . ?
O7 C7 C8 C9 -178.5(2) . . . . ?
F8 C8 C9 F9 0.1(4) . . . . ?
C7 C8 C9 F9 -178.6(2) . . . . ?
F8 C8 C9 C10 179.2(2) . . . . ?
C7 C8 C9 C10 0.5(4) . . . . ?
F9 C9 C10 C11 178.5(2) . . . . ?
C8 C9 C10 C11 -0.6(4) . . . . ?
C9 C10 C11 F11 -178.8(2) . . . . ?
C9 C10 C11 C12 0.9(4) . . . . ?
C8 C7 C12 F12 -180.0(2) . . . . ?
O7 C7 C12 F12 -2.2(3) . . . . ?
C8 C7 C12 C11 1.1(4) . . . . ?
O7 C7 C12 C11 178.8(2) . . . . ?
F11 C11 C12 F12 -0.4(4) . . . . ?
C10 C11 C12 F12 179.9(2) . . . . ?
F11 C11 C12 C7 178.6(2) . . . . ?
C10 C11 C12 C7 -1.2(4) . . . . ?
C1 C2 C13 C14 39.0(2) . . . . ?
C3 C2 C13 C14 -83.5(2) . . . . ?
C1 C2 C13 C18 -140.16(17) . . . . ?
C3 C2 C13 C18 97.3(2) . . . . ?
C18 C13 C14 C15 0.6(3) . . . . ?
C2 C13 C14 C15 -178.54(17) . . . . ?
C13 C14 C15 C16 -1.1(3) . . . . ?
C14 C15 C16 C17 0.2(3) . . . . ?
C14 C15 C16 C19 179.77(18) . . . . ?
C15 C16 C17 C18 1.2(3) . . . . ?
C19 C16 C17 C18 -178.44(18) . . . . ?
C16 C17 C18 C13 -1.6(3) . . . . ?
C14 C13 C18 C17 0.7(3) . . . . ?
C2 C13 C18 C17 179.85(17) . . . . ?
C2 C3 C20 C25 -144.80(17) . . . . ?
C4 C3 C20 C25 91.7(2) . . . . ?
C2 C3 C20 C21 32.8(2) . . . . ?
C4 C3 C20 C21 -90.7(2) . . . . ?
C25 C20 C21 C22 2.8(3) . . . . ?
C3 C20 C21 C22 -174.82(18) . . . . ?
C20 C21 C22 C23 -1.6(3) . . . . ?
C21 C22 C23 C24 -0.5(3) . . . . ?
C22 C23 C24 C25 1.3(3) . . . . ?
C23 C24 C25 C20 -0.1(3) . . . . ?
C21 C20 C25 C24 -1.9(3) . . . . ?
C3 C20 C25 C24 175.76(18) . . . . ?


#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.




_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Toluene'
####################################################################### 
# 
# 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_39
_database_code_depnum_ccdc_archive 'CCDC 2253986'
loop_
_audit_author_name
_audit_author_address
'David Cordes'
;University of St Andrews
United Kingdom
;
_audit_update_record             
;
2023-04-04 deposited with the CCDC.	2023-06-01 downloaded from the CCDC.
;
_audit_creation_date             2023-04-03
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.02.24 svn.rf166f9f3 for OlexSys, GUI svn.r6725)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H20 N2 O3'
_chemical_formula_sum            'C20 H20 N2 O3'
_chemical_formula_weight         336.38
_chemical_absolute_configuration rmad
_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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        P212121
_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                   7.83550(10)
_cell_length_b                   9.02620(10)
_cell_length_c                   26.1596(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1850.13(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    17156
_cell_measurement_temperature    125
_cell_measurement_theta_max      75.3900
_cell_measurement_theta_min      3.3590
_shelx_estimated_absorpt_T_max   0.987
_shelx_estimated_absorpt_T_min   0.873
_exptl_absorpt_coefficient_mu    0.664
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79731
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
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    1.208
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             712
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0281
_diffrn_reflns_av_unetI/netI     0.0159
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            21639
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.631
_diffrn_reflns_theta_min         3.379
_diffrn_ambient_temperature      125
_diffrn_detector                 'hybrid photon counting detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_detector_type            'Dectris PILATUS P200K'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -125.00  55.00   0.50    3.00    --  -35.00  60.00 -45.00  360
  2  ω   -108.00 -48.00   0.50    3.00    --  -35.00  30.00  90.00  120
  3  ω   -173.50 -10.00   0.50    5.00    -- -100.00  60.00 -90.00  327
  4  ω   -187.00 -40.00   0.50    5.00    -- -100.00  30.00  45.00  294
  5  ω   -165.00 -10.00   0.50    5.00    -- -100.00  60.00-180.00  310
  6  ω   -190.00-127.50   0.50    5.00    -- -100.00  60.00 135.00  125
  7  ω   -165.00 -19.00   0.50    5.00    -- -100.00  60.00   0.00  292
  8  ω   -152.50 -44.50   0.50    5.00    -- -100.00  30.00 135.00  216
  9  ω   -174.00-114.00   0.50    5.00    -- -100.00  60.00  90.00  120
 10  ω    -70.00 -10.00   0.50    5.00    -- -100.00  30.00   0.00  120
 11  ω   -190.00 -10.00   0.50    5.00    -- -100.00  30.00 -90.00  360
 12  ω   -174.00 -10.00   0.50    5.00    -- -100.00  60.00  45.00  328
 13  ω   -190.00-120.00   0.50    5.00    -- -100.00  60.00-135.00  140
;
_diffrn_measurement_device       'AFC11: Quarter χ 4 circle'
_diffrn_measurement_device_type  'Rigaku XtaLAB P200K'
_diffrn_measurement_method       'shutterless scans'
_diffrn_measurement_specimen_support Loop
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0696517000
_diffrn_orient_matrix_UB_12      0.1586167000
_diffrn_orient_matrix_UB_13      0.0061750000
_diffrn_orient_matrix_UB_21      -0.1816238000
_diffrn_orient_matrix_UB_22      0.0623455000
_diffrn_orient_matrix_UB_23      -0.0067055000
_diffrn_orient_matrix_UB_31      -0.0282515000
_diffrn_orient_matrix_UB_32      -0.0095971000
_diffrn_orient_matrix_UB_33      0.0581883000
_diffrn_radiation_monochromator  'Rigaku Osmic Confocal Optical System'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating Anode'
_diffrn_source_type              'Rigaku MM-007HF'
_reflns_Friedel_coverage         0.713
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.970
_reflns_number_gt                3690
_reflns_number_total             3772
_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 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_collection       
'CrystalClear-SM Expert 2.1 b45 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.165
_refine_diff_density_min         -0.160
_refine_diff_density_rms         0.038
_refine_ls_abs_structure_details 
;
 Flack x determined using 1524 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.03(8)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         3772
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0333
_refine_ls_R_factor_gt           0.0327
_refine_ls_restrained_S_all      1.049
_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)+(0.0515P)²+0.4169P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0903
_refine_ls_wR_factor_ref         0.0906
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 N5-H5A = N5-H5B
 0.98 with sigma of 0.02
3.a Ternary CH refined with riding coordinates:
 C4(H4), C2(H2), C3(H3)
3.b Aromatic/amide H refined with riding coordinates:
 C13(H13), C9(H9), C20(H20), C10(H10), C12(H12), C16(H16), C18(H18), C19(H19),
 C17(H17)
3.c Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C14(H14A,H14B,H14C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O5 O 0.37777(17) 0.29932(15) 0.50681(5) 0.0313(3) Uani 1 1 d . . . . .
O1 O 0.83661(18) 0.27230(17) 0.71666(5) 0.0340(3) Uani 1 1 d . . . . .
O2 O 0.91045(17) 0.19155(15) 0.63866(5) 0.0306(3) Uani 1 1 d . . . . .
N5 N 0.1568(2) 0.25770(19) 0.55957(6) 0.0294(3) Uani 1 1 d D . . . .
C5 C 0.3111(2) 0.30817(19) 0.54906(6) 0.0236(3) Uani 1 1 d . . . . .
N6 N 0.2246(3) 0.4597(2) 0.67042(7) 0.0412(4) Uani 1 1 d . . . . .
C1 C 0.8208(2) 0.26608(19) 0.66597(7) 0.0246(3) Uani 1 1 d . . . . .
C8 C 0.7582(2) 0.5035(2) 0.62326(7) 0.0253(4) Uani 1 1 d . . . . .
C6 C 0.3068(2) 0.4259(2) 0.63613(7) 0.0286(4) Uani 1 1 d . . . . .
C4 C 0.4131(2) 0.3816(2) 0.59239(6) 0.0245(4) Uani 1 1 d . . . . .
H4 H 0.464582 0.474047 0.578048 0.029 Uiso 1 1 calc R U . . .
C2 C 0.6789(2) 0.3659(2) 0.64702(6) 0.0243(4) Uani 1 1 d . . . . .
H2 H 0.608210 0.397060 0.676986 0.029 Uiso 1 1 calc R U . . .
C3 C 0.5638(2) 0.27995(19) 0.60940(6) 0.0234(3) Uani 1 1 d . . . . .
H3 H 0.633683 0.258520 0.578282 0.028 Uiso 1 1 calc R U . . .
C13 C 0.8339(3) 0.4996(2) 0.57502(7) 0.0304(4) Uani 1 1 d . . . . .
H13 H 0.834549 0.409836 0.556057 0.037 Uiso 1 1 calc R U . . .
C9 C 0.7606(3) 0.6373(2) 0.64993(7) 0.0315(4) Uani 1 1 d . . . . .
H9 H 0.709648 0.642686 0.682830 0.038 Uiso 1 1 calc R U . . .
C15 C 0.4991(2) 0.13250(19) 0.62956(7) 0.0265(4) Uani 1 1 d . . . . .
C11 C 0.9114(3) 0.7591(2) 0.58113(8) 0.0354(4) Uani 1 1 d . . . . .
C20 C 0.4440(3) 0.1144(2) 0.67969(8) 0.0364(5) Uani 1 1 d . . . . .
H20 H 0.451390 0.194670 0.703077 0.044 Uiso 1 1 calc R U . . .
C10 C 0.8360(3) 0.7623(2) 0.62919(8) 0.0382(4) Uani 1 1 d . . . . .
H10 H 0.836287 0.851992 0.648194 0.046 Uiso 1 1 calc R U . . .
C12 C 0.9083(3) 0.6257(2) 0.55451(8) 0.0350(4) Uani 1 1 d . . . . .
H12 H 0.958342 0.620947 0.521474 0.042 Uiso 1 1 calc R U . . .
C16 C 0.4891(3) 0.0129(2) 0.59646(8) 0.0347(4) Uani 1 1 d . . . . .
H16 H 0.528007 0.023054 0.562242 0.042 Uiso 1 1 calc R U . . .
C18 C 0.3670(3) -0.1392(2) 0.66225(10) 0.0464(6) Uani 1 1 d . . . . .
H18 H 0.321221 -0.231241 0.673300 0.056 Uiso 1 1 calc R U . . .
C7 C 0.9743(3) 0.1846(3) 0.73828(8) 0.0458(6) Uani 1 1 d . . . . .
H7A H 1.084034 0.222861 0.726098 0.069 Uiso 1 1 calc R U . . .
H7B H 0.961477 0.081104 0.727669 0.069 Uiso 1 1 calc R U . . .
H7C H 0.970151 0.190796 0.775661 0.069 Uiso 1 1 calc R U . . .
C19 C 0.3780(3) -0.0214(3) 0.69574(9) 0.0450(6) Uani 1 1 d . . . . .
H19 H 0.340311 -0.032888 0.730026 0.054 Uiso 1 1 calc R U . . .
C17 C 0.4226(3) -0.1222(2) 0.61287(10) 0.0454(5) Uani 1 1 d . . . . .
H17 H 0.415790 -0.203069 0.589707 0.054 Uiso 1 1 calc R U . . .
C14 C 0.9900(4) 0.8961(3) 0.55819(11) 0.0500(6) Uani 1 1 d . . . . .
H14A H 0.899442 0.964649 0.547787 0.075 Uiso 1 1 calc R U . . .
H14B H 1.058234 0.868554 0.528271 0.075 Uiso 1 1 calc R U . . .
H14C H 1.063359 0.944129 0.583589 0.075 Uiso 1 1 calc R U . . .
H5A H 0.113(3) 0.266(3) 0.5928(7) 0.030(5) Uiso 1 1 d D . . . .
H5B H 0.087(3) 0.225(3) 0.5321(8) 0.048(7) Uiso 1 1 d D . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O5 C5 1.225(2) . ?
O1 C1 1.333(2) . ?
O1 C7 1.452(3) . ?
O2 C1 1.207(2) . ?
N5 C5 1.321(2) . ?
N5 H5A 0.940(18) . ?
N5 H5B 0.95(2) . ?
C5 C4 1.537(2) . ?
N6 C6 1.146(3) . ?
C1 C2 1.515(2) . ?
C8 C2 1.521(2) . ?
C8 C13 1.395(3) . ?
C8 C9 1.395(3) . ?
C6 C4 1.471(3) . ?
C4 H4 1.0000 . ?
C4 C3 1.560(2) . ?
C2 H2 1.0000 . ?
C2 C3 1.544(2) . ?
C3 H3 1.0000 . ?
C3 C15 1.519(2) . ?
C13 H13 0.9500 . ?
C13 C12 1.387(3) . ?
C9 H9 0.9500 . ?
C9 C10 1.385(3) . ?
C15 C20 1.390(3) . ?
C15 C16 1.386(3) . ?
C11 C10 1.389(3) . ?
C11 C12 1.390(3) . ?
C11 C14 1.506(3) . ?
C20 H20 0.9500 . ?
C20 C19 1.395(3) . ?
C10 H10 0.9500 . ?
C12 H12 0.9500 . ?
C16 H16 0.9500 . ?
C16 C17 1.394(3) . ?
C18 H18 0.9500 . ?
C18 C19 1.381(4) . ?
C18 C17 1.372(4) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C19 H19 0.9500 . ?
C17 H17 0.9500 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 C7 115.68(15) . . ?
C5 N5 H5A 120.1(14) . . ?
C5 N5 H5B 118.5(16) . . ?
H5A N5 H5B 121(2) . . ?
O5 C5 N5 123.73(17) . . ?
O5 C5 C4 118.15(16) . . ?
N5 C5 C4 118.11(15) . . ?
O1 C1 C2 111.62(14) . . ?
O2 C1 O1 123.94(17) . . ?
O2 C1 C2 124.43(16) . . ?
C13 C8 C2 121.54(16) . . ?
C13 C8 C9 117.94(17) . . ?
C9 C8 C2 120.51(16) . . ?
N6 C6 C4 179.5(2) . . ?
C5 C4 H4 107.0 . . ?
C5 C4 C3 110.51(14) . . ?
C6 C4 C5 113.36(15) . . ?
C6 C4 H4 107.0 . . ?
C6 C4 C3 111.51(14) . . ?
C3 C4 H4 107.0 . . ?
C1 C2 C8 108.61(15) . . ?
C1 C2 H2 108.5 . . ?
C1 C2 C3 109.77(14) . . ?
C8 C2 H2 108.5 . . ?
C8 C2 C3 112.86(14) . . ?
C3 C2 H2 108.5 . . ?
C4 C3 H3 107.2 . . ?
C2 C3 C4 109.17(14) . . ?
C2 C3 H3 107.2 . . ?
C15 C3 C4 111.21(14) . . ?
C15 C3 C2 114.46(14) . . ?
C15 C3 H3 107.2 . . ?
C8 C13 H13 119.7 . . ?
C12 C13 C8 120.54(17) . . ?
C12 C13 H13 119.7 . . ?
C8 C9 H9 119.5 . . ?
C10 C9 C8 121.03(18) . . ?
C10 C9 H9 119.5 . . ?
C20 C15 C3 122.29(17) . . ?
C16 C15 C3 118.98(16) . . ?
C16 C15 C20 118.70(18) . . ?
C10 C11 C12 117.65(18) . . ?
C10 C11 C14 121.1(2) . . ?
C12 C11 C14 121.2(2) . . ?
C15 C20 H20 119.9 . . ?
C15 C20 C19 120.1(2) . . ?
C19 C20 H20 119.9 . . ?
C9 C10 C11 121.24(18) . . ?
C9 C10 H10 119.4 . . ?
C11 C10 H10 119.4 . . ?
C13 C12 C11 121.60(19) . . ?
C13 C12 H12 119.2 . . ?
C11 C12 H12 119.2 . . ?
C15 C16 H16 119.7 . . ?
C15 C16 C17 120.7(2) . . ?
C17 C16 H16 119.7 . . ?
C19 C18 H18 120.3 . . ?
C17 C18 H18 120.3 . . ?
C17 C18 C19 119.4(2) . . ?
O1 C7 H7A 109.5 . . ?
O1 C7 H7B 109.5 . . ?
O1 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C20 C19 H19 119.7 . . ?
C18 C19 C20 120.6(2) . . ?
C18 C19 H19 119.7 . . ?
C16 C17 H17 119.8 . . ?
C18 C17 C16 120.4(2) . . ?
C18 C17 H17 119.8 . . ?
C11 C14 H14A 109.5 . . ?
C11 C14 H14B 109.5 . . ?
C11 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N5 H5A O2 0.940(18) 2.10(2) 2.892(2) 141.3(19) 1_455 yes
N5 H5B O5 0.95(2) 1.94(2) 2.839(2) 156(2) 4_456 yes

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O5 C5 C4 C6 162.97(16) . . . . ?
O5 C5 C4 C3 -71.0(2) . . . . ?
O1 C1 C2 C8 104.23(16) . . . . ?
O1 C1 C2 C3 -131.95(15) . . . . ?
O2 C1 C2 C8 -74.8(2) . . . . ?
O2 C1 C2 C3 49.0(2) . . . . ?
N5 C5 C4 C6 -17.3(2) . . . . ?
N5 C5 C4 C3 108.74(18) . . . . ?
C5 C4 C3 C2 171.67(13) . . . . ?
C5 C4 C3 C15 -61.09(18) . . . . ?
C1 C2 C3 C4 177.15(14) . . . . ?
C1 C2 C3 C15 51.77(19) . . . . ?
C8 C2 C3 C4 -61.54(18) . . . . ?
C8 C2 C3 C15 173.08(15) . . . . ?
C8 C13 C12 C11 0.5(3) . . . . ?
C8 C9 C10 C11 0.2(3) . . . . ?
C6 C4 C3 C2 -61.28(18) . . . . ?
C6 C4 C3 C15 65.96(19) . . . . ?
C4 C3 C15 C20 -83.5(2) . . . . ?
C4 C3 C15 C16 94.4(2) . . . . ?
C2 C8 C13 C12 -178.80(19) . . . . ?
C2 C8 C9 C10 178.46(18) . . . . ?
C2 C3 C15 C20 40.8(2) . . . . ?
C2 C3 C15 C16 -141.35(18) . . . . ?
C3 C15 C20 C19 176.91(19) . . . . ?
C3 C15 C16 C17 -176.85(19) . . . . ?
C13 C8 C2 C1 75.8(2) . . . . ?
C13 C8 C2 C3 -46.2(2) . . . . ?
C13 C8 C9 C10 -0.1(3) . . . . ?
C9 C8 C2 C1 -102.72(19) . . . . ?
C9 C8 C2 C3 135.32(18) . . . . ?
C9 C8 C13 C12 -0.2(3) . . . . ?
C15 C20 C19 C18 0.2(4) . . . . ?
C15 C16 C17 C18 -0.5(4) . . . . ?
C20 C15 C16 C17 1.0(3) . . . . ?
C10 C11 C12 C13 -0.4(3) . . . . ?
C12 C11 C10 C9 0.0(3) . . . . ?
C16 C15 C20 C19 -0.9(3) . . . . ?
C7 O1 C1 O2 1.4(3) . . . . ?
C7 O1 C1 C2 -177.61(17) . . . . ?
C19 C18 C17 C16 -0.3(4) . . . . ?
C17 C18 C19 C20 0.4(4) . . . . ?
C14 C11 C10 C9 178.7(2) . . . . ?
C14 C11 C12 C13 -179.0(2) . . . . ?


#===END
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Chloroform/petroleum ether'
