# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_ben_ina_2_1_sub
_database_code_depnum_ccdc_archive 'CCDC 1982619'
loop_
_audit_author_name
_audit_author_address
'patrick mcardle'
;NUI, Galway
Republic of Ireland
;
_audit_update_record             
;
2020-02-07 deposited with the CCDC.	2020-04-15 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT026_ben_ina_2_1_sub     
;
PROBLEM: Ratio Observed / Unique Reflections (too) Low ..        29% Check
RESPONSE: The crystal was a weak diffracter.
;
_vrf_PLAT910_ben_ina_2_1_sub     
;
PROBLEM: Missing # of FCF Reflection(s) Below Theta(Min).         19 Note
RESPONSE: These reflections are behind the beam stop.
;
# Added during the CSD deposition process: Friday 07 February 2020 11:01 AM
# end Validation Reply Form


_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H18 N2 O5'
_chemical_formula_weight         366.36

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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. 
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.0493(6)
_cell_length_b                   12.6674(11)
_cell_length_c                   14.6060(13)
_cell_angle_alpha                79.358(7)
_cell_angle_beta                 80.034(6)
_cell_angle_gamma                89.938(6)
_cell_volume                     1798.9(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    300.0(2)
_cell_measurement_reflns_used    1823
_cell_measurement_theta_min      3.7740
_cell_measurement_theta_max      25.2990

_exptl_crystal_description       Parallelepiped
_exptl_crystal_colour            Colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.353
_exptl_crystal_F_000             768
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.20
_exptl_absorpt_coefficient_mu    0.098
_shelx_estimated_absorpt_T_min   0.952
_shelx_estimated_absorpt_T_max   0.981
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.80775
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
; 
crysalispro 1.171.40.14e (rigaku oxford diffraction, 2018) 
empirical absorption correction using spherical harmonics, 
 implemented in scale3 abspack scaling algorithm. 
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      300.0(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed x-ray tube'
_diffrn_measurement_device_type  'xcalibur, sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 16.1048
_diffrn_reflns_number            15274
_diffrn_reflns_av_unetI/netI     0.1682
_diffrn_reflns_av_R_equivalents  0.0577
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         3.573
_diffrn_reflns_theta_max         29.259
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.852
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.852
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.852
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             8353
_reflns_number_gt                2426
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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. 
;

_computing_data_collection       'crysalispro 1.171.40.14e (rigaku od, 2018)'
_computing_cell_refinement       'crysalispro 1.171.40.14e (rigaku od, 2018)'
_computing_data_reduction        'crysalispro 1.171.40.14e (rigaku od, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    
'ORTEX - P. McArdle, J.Appl.Cryst.,1995,28,65-65.'
_computing_publication_material  
'Oscail - P. McArdle, J.Appl.Cryst.,2017,50,320-326.'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0693P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         8353
_refine_ls_number_parameters     491
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2271
_refine_ls_R_factor_gt           0.0786
_refine_ls_wR_factor_ref         0.2530
_refine_ls_wR_factor_gt          0.1727
_refine_ls_goodness_of_fit_ref   0.896
_refine_ls_restrained_S_all      0.896
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 -0.0953(3) 0.6034(3) 0.2628(2) 0.0573(9) Uani 1 1 d . . . . .
O2 O -0.0700(3) 0.7541(2) 0.3161(2) 0.0532(8) Uani 1 1 d . . . . .
H1O2 H -0.024654 0.715236 0.349307 0.069 Uiso 1 1 calc R U . . .
O3 O 0.0980(3) 0.6496(2) 0.4230(2) 0.0542(9) Uani 1 1 d . . . . .
O4 O 0.5906(3) 0.3710(2) 0.7157(2) 0.0496(8) Uani 1 1 d . . . . .
H4 H 0.530994 0.389071 0.684666 0.065 Uiso 1 1 calc R U . . .
O5 O 0.5756(3) 0.2192(2) 0.6621(2) 0.0570(9) Uani 1 1 d . . . . .
O6 O 1.1553(3) 0.2808(2) 0.3373(2) 0.0554(9) Uani 1 1 d . . . . .
O7 O 1.1975(3) 0.1301(2) 0.2825(2) 0.0508(8) Uani 1 1 d . . . . .
H1O7 H 1.124253 0.110708 0.315854 0.066 Uiso 1 1 calc R U . . .
O8 O 0.5595(3) -0.1490(3) 0.5770(2) 0.0556(9) Uani 1 1 d . . . . .
O9 O 0.3369(3) -0.2532(2) 0.6830(2) 0.0509(8) Uani 1 1 d . . . . .
H9 H 0.396964 -0.214140 0.647793 0.066 Uiso 1 1 calc R U . . .
O10 O 0.2856(3) -0.1039(2) 0.7382(2) 0.0569(9) Uani 1 1 d . . . . .
N1 N 0.0904(3) 0.4952(3) 0.3710(3) 0.0535(10) Uani 1 1 d . . . . .
H1A H 0.036141 0.519394 0.333119 0.070 Uiso 1 1 calc R U . . .
H1B H 0.117503 0.430414 0.374313 0.070 Uiso 1 1 calc R U . . .
N2 N 0.4093(3) 0.4327(3) 0.6043(3) 0.0458(9) Uani 1 1 d . . . . .
N3 N 0.5267(3) 0.0058(3) 0.6285(3) 0.0530(10) Uani 1 1 d . . . . .
H3A H 0.452640 -0.017059 0.666082 0.069 Uiso 1 1 calc R U . . .
H3B H 0.556817 0.070197 0.624855 0.069 Uiso 1 1 calc R U . . .
N4 N 0.9617(3) 0.0663(3) 0.3952(2) 0.0424(9) Uani 1 1 d . . . . .
C1 C -0.3739(4) 0.8616(4) 0.0849(3) 0.0583(13) Uani 1 1 d . . . . .
H1 H -0.429747 0.896501 0.045072 0.076 Uiso 1 1 calc R U . . .
C2 C -0.3104(5) 0.9196(4) 0.1366(4) 0.0663(15) Uani 1 1 d . . . . .
H2 H -0.322815 0.993031 0.131659 0.086 Uiso 1 1 calc R U . . .
C3 C -0.2279(4) 0.8676(4) 0.1959(3) 0.0531(12) Uani 1 1 d . . . . .
H3 H -0.185442 0.906009 0.231741 0.069 Uiso 1 1 calc R U . . .
C4 C -0.2083(4) 0.7589(4) 0.2022(3) 0.0411(10) Uani 1 1 d . . . . .
C5 C -0.1199(4) 0.6980(4) 0.2617(3) 0.0484(12) Uani 1 1 d . . . . .
C6 C -0.2748(4) 0.7025(4) 0.1496(3) 0.0502(12) Uani 1 1 d . . . . .
H6 H -0.263597 0.628899 0.154325 0.065 Uiso 1 1 calc R U . . .
C7 C -0.3565(4) 0.7537(4) 0.0909(3) 0.0594(14) Uani 1 1 d . . . . .
H7 H -0.399887 0.715540 0.055350 0.077 Uiso 1 1 calc R U . . .
C8 C 0.1314(4) 0.5563(4) 0.4231(3) 0.0408(10) Uani 1 1 d . . . . .
C9 C 0.2310(4) 0.5101(3) 0.4872(3) 0.0387(10) Uani 1 1 d . . . . .
C10 C 0.2701(4) 0.5741(4) 0.5431(3) 0.0499(12) Uani 1 1 d . . . . .
H10 H 0.237820 0.642910 0.542977 0.065 Uiso 1 1 calc R U . . .
C11 C 0.3664(4) 0.5289(4) 0.6043(3) 0.0494(12) Uani 1 1 d . . . . .
H11 H 0.396753 0.570288 0.643383 0.064 Uiso 1 1 calc R U . . .
C12 C 0.3731(4) 0.3705(4) 0.5513(3) 0.0489(12) Uani 1 1 d . . . . .
H12 H 0.407286 0.302096 0.552970 0.064 Uiso 1 1 calc R U . . .
C13 C 0.2771(4) 0.4098(4) 0.4886(3) 0.0477(12) Uani 1 1 d . . . . .
H13 H 0.248529 0.366349 0.450460 0.062 Uiso 1 1 calc R U . . .
C14 C 0.6176(4) 0.2706(4) 0.7143(3) 0.0418(11) Uani 1 1 d . . . . .
C15 C 0.7045(4) 0.2233(4) 0.7837(3) 0.0414(10) Uani 1 1 d . . . . .
C16 C 0.7549(4) 0.2861(4) 0.8400(3) 0.0495(12) Uani 1 1 d . . . . .
H16 H 0.734803 0.358425 0.834234 0.064 Uiso 1 1 calc R U . . .
C17 C 0.8342(5) 0.2409(5) 0.9041(4) 0.0636(14) Uani 1 1 d . . . . .
H17 H 0.868805 0.282847 0.940993 0.083 Uiso 1 1 calc R U . . .
C18 C 0.8620(5) 0.1327(5) 0.9134(4) 0.0656(14) Uani 1 1 d . . . . .
H18 H 0.913608 0.101513 0.957646 0.085 Uiso 1 1 calc R U . . .
C19 C 0.8132(5) 0.0711(4) 0.8567(4) 0.0721(16) Uani 1 1 d . . . . .
H19 H 0.832934 -0.001301 0.862493 0.094 Uiso 1 1 calc R U . . .
C20 C 0.7357(4) 0.1165(4) 0.7920(4) 0.0561(13) Uani 1 1 d . . . . .
H20 H 0.703994 0.074863 0.753647 0.073 Uiso 1 1 calc R U . . .
C21 C 1.2240(4) 0.2291(4) 0.2859(3) 0.0433(11) Uani 1 1 d . . . . .
C22 C 1.3468(4) 0.2752(3) 0.2168(3) 0.0399(10) Uani 1 1 d . . . . .
C23 C 1.3792(4) 0.3831(4) 0.2075(3) 0.0568(13) Uani 1 1 d . . . . .
H23 H 1.325700 0.425124 0.244177 0.074 Uiso 1 1 calc R U . . .
C24 C 1.4920(5) 0.4286(4) 0.1433(4) 0.0726(16) Uani 1 1 d . . . . .
H24 H 1.513595 0.501232 0.137077 0.094 Uiso 1 1 calc R U . . .
C25 C 1.5708(5) 0.3679(5) 0.0896(4) 0.0670(15) Uani 1 1 d . . . . .
H25 H 1.644647 0.399633 0.045684 0.087 Uiso 1 1 calc R U . . .
C26 C 1.5422(4) 0.2591(4) 0.0997(3) 0.0599(14) Uani 1 1 d . . . . .
H26 H 1.598659 0.216958 0.065015 0.078 Uiso 1 1 calc R U . . .
C27 C 1.4279(4) 0.2137(4) 0.1624(3) 0.0472(12) Uani 1 1 d . . . . .
H27 H 1.405920 0.141305 0.167734 0.061 Uiso 1 1 calc R U . . .
C28 C 0.8983(4) 0.1280(4) 0.4489(3) 0.0465(11) Uani 1 1 d . . . . .
H28 H 0.933975 0.196233 0.447203 0.060 Uiso 1 1 calc R U . . .
C29 C 0.7719(4) 0.0911(3) 0.5117(3) 0.0462(11) Uani 1 1 d . . . . .
H29 H 0.725074 0.134739 0.550121 0.060 Uiso 1 1 calc R U . . .
C30 C 0.7246(4) -0.0093(3) 0.5122(3) 0.0377(10) Uani 1 1 d . . . . .
C31 C 0.5924(4) -0.0564(4) 0.5777(3) 0.0452(11) Uani 1 1 d . . . . .
C32 C 0.7912(4) -0.0737(4) 0.4558(3) 0.0492(12) Uani 1 1 d . . . . .
H32 H 0.757928 -0.142070 0.455452 0.064 Uiso 1 1 calc R U . . .
C33 C 0.9177(4) -0.0296(4) 0.3957(3) 0.0511(12) Uani 1 1 d . . . . .
H33 H 0.967618 -0.071517 0.356972 0.066 Uiso 1 1 calc R U . . .
C34 C 0.2617(4) -0.1968(4) 0.7381(3) 0.0439(11) Uani 1 1 d . . . . .
C35 C 0.1425(4) -0.2588(4) 0.7991(3) 0.0416(10) Uani 1 1 d . . . . .
C36 C 0.0539(4) -0.2013(4) 0.8536(3) 0.0514(12) Uani 1 1 d . . . . .
H36 H 0.068789 -0.127982 0.849619 0.067 Uiso 1 1 calc R U . . .
C37 C -0.0567(4) -0.2543(4) 0.9138(3) 0.0599(14) Uani 1 1 d . . . . .
H37 H -0.116544 -0.216730 0.950934 0.078 Uiso 1 1 calc R U . . .
C38 C -0.0785(5) -0.3619(4) 0.9190(4) 0.0631(14) Uani 1 1 d . . . . .
H38 H -0.152709 -0.397179 0.960250 0.082 Uiso 1 1 calc R U . . .
C39 C 0.0087(5) -0.4187(4) 0.8634(4) 0.0626(15) Uani 1 1 d . . . . .
H39 H -0.006862 -0.491868 0.867039 0.081 Uiso 1 1 calc R U . . .
C40 C 0.1182(4) -0.3665(4) 0.8030(3) 0.0524(12) Uani 1 1 d . . . . .
H40 H 0.176168 -0.403970 0.764477 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
O1 C5 1.221(5) . ?
O2 C5 1.317(5) . ?
O2 H1O2 0.8200 . ?
O3 C8 1.228(4) . ?
O4 C14 1.304(5) . ?
O4 H4 0.8200 . ?
O5 C14 1.216(5) . ?
O6 C21 1.213(5) . ?
O7 C21 1.294(5) . ?
O7 H1O7 0.8200 . ?
O8 C31 1.221(4) . ?
O9 C34 1.316(4) . ?
O9 H9 0.8200 . ?
O10 C34 1.201(5) . ?
N1 C8 1.293(5) . ?
N1 H1A 0.8600 . ?
N1 H1B 0.8600 . ?
N2 C11 1.293(5) . ?
N2 C12 1.294(5) . ?
N3 C31 1.285(5) . ?
N3 H3A 0.8600 . ?
N3 H3B 0.8600 . ?
N4 C33 1.292(5) . ?
N4 C28 1.298(5) . ?
C1 C7 1.366(6) . ?
C1 C2 1.374(6) . ?
C1 H1 0.9300 . ?
C2 C3 1.382(6) . ?
C2 H2 0.9300 . ?
C3 C4 1.378(6) . ?
C3 H3 0.9300 . ?
C4 C6 1.390(5) . ?
C4 C5 1.469(6) . ?
C6 C7 1.366(6) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C8 C9 1.530(6) . ?
C9 C13 1.350(5) . ?
C9 C10 1.355(5) . ?
C10 C11 1.473(6) . ?
C10 H10 0.9300 . ?
C11 H11 0.9300 . ?
C12 C13 1.468(6) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C14 C15 1.493(6) . ?
C15 C20 1.376(6) . ?
C15 C16 1.397(6) . ?
C16 C17 1.378(6) . ?
C16 H16 0.9300 . ?
C17 C18 1.385(7) . ?
C17 H17 0.9300 . ?
C18 C19 1.384(7) . ?
C18 H18 0.9300 . ?
C19 C20 1.372(6) . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?
C21 C22 1.494(5) . ?
C22 C27 1.381(5) . ?
C22 C23 1.382(6) . ?
C23 C24 1.389(6) . ?
C23 H23 0.9300 . ?
C24 C25 1.356(7) . ?
C24 H24 0.9300 . ?
C25 C26 1.383(7) . ?
C25 H25 0.9300 . ?
C26 C27 1.389(5) . ?
C26 H26 0.9300 . ?
C27 H27 0.9300 . ?
C28 C29 1.454(5) . ?
C28 H28 0.9300 . ?
C29 C30 1.356(5) . ?
C29 H29 0.9300 . ?
C30 C32 1.360(5) . ?
C30 C31 1.545(5) . ?
C32 C33 1.460(6) . ?
C32 H32 0.9300 . ?
C33 H33 0.9300 . ?
C34 C35 1.489(6) . ?
C35 C40 1.376(5) . ?
C35 C36 1.387(5) . ?
C36 C37 1.380(6) . ?
C36 H36 0.9300 . ?
C37 C38 1.366(6) . ?
C37 H37 0.9300 . ?
C38 C39 1.384(6) . ?
C38 H38 0.9300 . ?
C39 C40 1.370(6) . ?
C39 H39 0.9300 . ?
C40 H40 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
C5 O2 H1O2 109.5 . . ?
C14 O4 H4 109.5 . . ?
C21 O7 H1O7 109.5 . . ?
C34 O9 H9 109.5 . . ?
C8 N1 H1A 120.0 . . ?
C8 N1 H1B 120.0 . . ?
H1A N1 H1B 120.0 . . ?
C11 N2 C12 123.3(4) . . ?
C31 N3 H3A 120.0 . . ?
C31 N3 H3B 120.0 . . ?
H3A N3 H3B 120.0 . . ?
C33 N4 C28 122.4(4) . . ?
C7 C1 C2 121.2(5) . . ?
C7 C1 H1 119.4 . . ?
C2 C1 H1 119.4 . . ?
C1 C2 C3 119.3(5) . . ?
C1 C2 H2 120.3 . . ?
C3 C2 H2 120.3 . . ?
C4 C3 C2 120.3(5) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?
C3 C4 C6 119.0(5) . . ?
C3 C4 C5 123.8(4) . . ?
C6 C4 C5 117.2(4) . . ?
O1 C5 O2 122.1(5) . . ?
O1 C5 C4 123.9(4) . . ?
O2 C5 C4 114.0(4) . . ?
C7 C6 C4 120.8(5) . . ?
C7 C6 H6 119.6 . . ?
C4 C6 H6 119.6 . . ?
C1 C7 C6 119.4(5) . . ?
C1 C7 H7 120.3 . . ?
C6 C7 H7 120.3 . . ?
O3 C8 N1 124.4(4) . . ?
O3 C8 C9 117.8(4) . . ?
N1 C8 C9 117.8(4) . . ?
C13 C9 C10 121.4(5) . . ?
C13 C9 C8 121.6(4) . . ?
C10 C9 C8 117.1(4) . . ?
C9 C10 C11 116.6(4) . . ?
C9 C10 H10 121.7 . . ?
C11 C10 H10 121.7 . . ?
N2 C11 C10 120.9(4) . . ?
N2 C11 H11 119.5 . . ?
C10 C11 H11 119.5 . . ?
N2 C12 C13 118.9(4) . . ?
N2 C12 H12 120.5 . . ?
C13 C12 H12 120.5 . . ?
C9 C13 C12 118.9(4) . . ?
C9 C13 H13 120.6 . . ?
C12 C13 H13 120.6 . . ?
O5 C14 O4 123.6(4) . . ?
O5 C14 C15 122.6(4) . . ?
O4 C14 C15 113.8(4) . . ?
C20 C15 C16 119.6(5) . . ?
C20 C15 C14 119.5(4) . . ?
C16 C15 C14 120.8(4) . . ?
C17 C16 C15 120.1(5) . . ?
C17 C16 H16 120.0 . . ?
C15 C16 H16 120.0 . . ?
C16 C17 C18 119.7(5) . . ?
C16 C17 H17 120.2 . . ?
C18 C17 H17 120.2 . . ?
C19 C18 C17 120.0(5) . . ?
C19 C18 H18 120.0 . . ?
C17 C18 H18 120.0 . . ?
C20 C19 C18 120.2(5) . . ?
C20 C19 H19 119.9 . . ?
C18 C19 H19 119.9 . . ?
C19 C20 C15 120.3(5) . . ?
C19 C20 H20 119.8 . . ?
C15 C20 H20 119.8 . . ?
O6 C21 O7 124.3(4) . . ?
O6 C21 C22 122.9(4) . . ?
O7 C21 C22 112.8(4) . . ?
C27 C22 C23 119.3(4) . . ?
C27 C22 C21 122.2(4) . . ?
C23 C22 C21 118.5(4) . . ?
C22 C23 C24 119.9(5) . . ?
C22 C23 H23 120.1 . . ?
C24 C23 H23 120.1 . . ?
C25 C24 C23 120.5(5) . . ?
C25 C24 H24 119.7 . . ?
C23 C24 H24 119.7 . . ?
C24 C25 C26 120.5(5) . . ?
C24 C25 H25 119.7 . . ?
C26 C25 H25 119.7 . . ?
C25 C26 C27 119.2(5) . . ?
C25 C26 H26 120.4 . . ?
C27 C26 H26 120.4 . . ?
C22 C27 C26 120.6(4) . . ?
C22 C27 H27 119.7 . . ?
C26 C27 H27 119.7 . . ?
N4 C28 C29 120.3(4) . . ?
N4 C28 H28 119.8 . . ?
C29 C28 H28 119.8 . . ?
C30 C29 C28 117.7(4) . . ?
C30 C29 H29 121.2 . . ?
C28 C29 H29 121.2 . . ?
C29 C30 C32 121.8(4) . . ?
C29 C30 C31 121.5(4) . . ?
C32 C30 C31 116.7(4) . . ?
O8 C31 N3 125.7(4) . . ?
O8 C31 C30 117.5(4) . . ?
N3 C31 C30 116.7(4) . . ?
C30 C32 C33 116.4(4) . . ?
C30 C32 H32 121.8 . . ?
C33 C32 H32 121.8 . . ?
N4 C33 C32 121.4(4) . . ?
N4 C33 H33 119.3 . . ?
C32 C33 H33 119.3 . . ?
O10 C34 O9 123.3(4) . . ?
O10 C34 C35 123.3(4) . . ?
O9 C34 C35 113.4(4) . . ?
C40 C35 C36 120.4(4) . . ?
C40 C35 C34 123.6(4) . . ?
C36 C35 C34 116.0(4) . . ?
C37 C36 C35 119.1(4) . . ?
C37 C36 H36 120.5 . . ?
C35 C36 H36 120.5 . . ?
C38 C37 C36 120.2(5) . . ?
C38 C37 H37 119.9 . . ?
C36 C37 H37 119.9 . . ?
C37 C38 C39 120.6(5) . . ?
C37 C38 H38 119.7 . . ?
C39 C38 H38 119.7 . . ?
C40 C39 C38 119.5(5) . . ?
C40 C39 H39 120.2 . . ?
C38 C39 H39 120.2 . . ?
C39 C40 C35 120.1(4) . . ?
C39 C40 H40 120.0 . . ?
C35 C40 H40 120.0 . . ?

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 C1 C2 C3 -0.2(7) . . . . ?
C1 C2 C3 C4 0.8(7) . . . . ?
C2 C3 C4 C6 -1.3(7) . . . . ?
C2 C3 C4 C5 178.5(4) . . . . ?
C3 C4 C5 O1 -175.0(4) . . . . ?
C6 C4 C5 O1 4.9(6) . . . . ?
C3 C4 C5 O2 6.1(6) . . . . ?
C6 C4 C5 O2 -174.1(4) . . . . ?
C3 C4 C6 C7 1.3(6) . . . . ?
C5 C4 C6 C7 -178.6(4) . . . . ?
C2 C1 C7 C6 0.2(7) . . . . ?
C4 C6 C7 C1 -0.7(7) . . . . ?
O3 C8 C9 C13 -177.3(4) . . . . ?
N1 C8 C9 C13 1.2(6) . . . . ?
O3 C8 C9 C10 3.3(5) . . . . ?
N1 C8 C9 C10 -178.3(4) . . . . ?
C13 C9 C10 C11 0.8(6) . . . . ?
C8 C9 C10 C11 -179.8(3) . . . . ?
C12 N2 C11 C10 0.7(6) . . . . ?
C9 C10 C11 N2 -0.7(6) . . . . ?
C11 N2 C12 C13 -0.8(6) . . . . ?
C10 C9 C13 C12 -0.9(6) . . . . ?
C8 C9 C13 C12 179.7(3) . . . . ?
N2 C12 C13 C9 0.9(6) . . . . ?
O5 C14 C15 C20 -2.3(6) . . . . ?
O4 C14 C15 C20 177.3(4) . . . . ?
O5 C14 C15 C16 177.6(4) . . . . ?
O4 C14 C15 C16 -2.8(5) . . . . ?
C20 C15 C16 C17 -0.6(6) . . . . ?
C14 C15 C16 C17 179.5(4) . . . . ?
C15 C16 C17 C18 -0.9(7) . . . . ?
C16 C17 C18 C19 1.6(7) . . . . ?
C17 C18 C19 C20 -0.8(8) . . . . ?
C18 C19 C20 C15 -0.8(8) . . . . ?
C16 C15 C20 C19 1.4(7) . . . . ?
C14 C15 C20 C19 -178.7(4) . . . . ?
O6 C21 C22 C27 176.5(4) . . . . ?
O7 C21 C22 C27 -5.5(6) . . . . ?
O6 C21 C22 C23 -3.6(7) . . . . ?
O7 C21 C22 C23 174.4(4) . . . . ?
C27 C22 C23 C24 0.5(7) . . . . ?
C21 C22 C23 C24 -179.4(4) . . . . ?
C22 C23 C24 C25 -0.1(8) . . . . ?
C23 C24 C25 C26 -1.7(9) . . . . ?
C24 C25 C26 C27 3.0(8) . . . . ?
C23 C22 C27 C26 0.9(7) . . . . ?
C21 C22 C27 C26 -179.3(4) . . . . ?
C25 C26 C27 C22 -2.6(7) . . . . ?
C33 N4 C28 C29 -0.9(7) . . . . ?
N4 C28 C29 C30 0.5(7) . . . . ?
C28 C29 C30 C32 -0.6(6) . . . . ?
C28 C29 C30 C31 178.9(4) . . . . ?
C29 C30 C31 O8 -177.0(4) . . . . ?
C32 C30 C31 O8 2.6(6) . . . . ?
C29 C30 C31 N3 2.9(6) . . . . ?
C32 C30 C31 N3 -177.5(4) . . . . ?
C29 C30 C32 C33 1.0(7) . . . . ?
C31 C30 C32 C33 -178.6(3) . . . . ?
C28 N4 C33 C32 1.4(7) . . . . ?
C30 C32 C33 N4 -1.4(7) . . . . ?
O10 C34 C35 C40 -176.6(5) . . . . ?
O9 C34 C35 C40 4.5(6) . . . . ?
O10 C34 C35 C36 3.6(7) . . . . ?
O9 C34 C35 C36 -175.3(4) . . . . ?
C40 C35 C36 C37 2.0(7) . . . . ?
C34 C35 C36 C37 -178.2(4) . . . . ?
C35 C36 C37 C38 -0.4(8) . . . . ?
C36 C37 C38 C39 -0.7(8) . . . . ?
C37 C38 C39 C40 0.3(8) . . . . ?
C38 C39 C40 C35 1.3(8) . . . . ?
C36 C35 C40 C39 -2.5(7) . . . . ?
C34 C35 C40 C39 177.7(4) . . . . ?

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
O4 H4 N2 0.82 1.85 2.670(5) 174.5 . yes
O7 H1O7 N4 0.82 1.85 2.673(4) 177.9 . yes
O9 H9 O8 0.82 1.88 2.683(4) 167.2 . yes
O2 H1O2 O3 0.82 1.87 2.680(4) 169.5 . yes
N3 H3A O10 0.86 2.03 2.865(4) 165.3 . yes
N3 H3B O5 0.86 2.08 2.893(5) 158.4 . yes
N1 H1A O1 0.86 2.00 2.842(5) 166.4 . yes
N1 H1B O6 0.86 2.08 2.903(5) 159.3 1_455 yes
C11 H11 O9 0.93 2.46 3.175(5) 133.7 1_565 yes
C12 H12 O5 0.93 2.61 3.228(6) 124.4 . yes
C13 H13 O6 0.93 2.45 3.366(5) 169.8 1_455 yes
C28 H28 O6 0.93 2.61 3.234(5) 125.1 . yes
C29 H29 O5 0.93 2.42 3.341(5) 169.3 . yes
C33 H33 O2 0.93 2.44 3.162(6) 134.6 1_645 yes

_refine_diff_density_max         0.394
_refine_diff_density_min         -0.251
_refine_diff_density_rms         0.056

####################################################################### 
# 
# 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_dif_ina_s1
_database_code_depnum_ccdc_archive 'CCDC 1982620'
loop_
_audit_author_name
_audit_author_address
'Patrick McArdle'
;NUI, Galway
Republic of Ireland
;
_audit_update_record             
;
2020-04-12 deposited with the CCDC.	2020-04-15 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_RINTA01_dif_ina_s1          
;
PROBLEM: The value of Rint is greater than 0.18
RESPONSE: The crystal was a weak diffracter and was twinned. CrysAlisPro 171.40.14e was used to detwin the data and the structure was refined with ShelxL HKLF 5 BASF 0.29179. Partially overlapped reflections may have contributed to detwin difficulties and the high Rint
;
_vrf_PLAT082_dif_ina_s1          
;
PROBLEM: High R1 Value ..................................       0.17 Report
RESPONSE: The crystal was a weak diffracter and that and the high Rint led to the high R1.
;
_vrf_PLAT084_dif_ina_s1          
;
PROBLEM: High wR2 Value (i.e. > 0.25) ...................       0.37 Report
RESPONSE: The crystal was a weak diffracter and that and the high Rint led to the high R2.
;
_vrf_PLAT340_dif_ina_s1          
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.01494 Ang.
RESPONSE: This was due to the poor quality of the diffraction.
;
_vrf_PLAT910_dif_ina_s1          
;
PROBLEM: Missing # of FCF Reflection(s) Below Theta(Min).         17 Note
RESPONSE: These reflections are behind the beam stop.
;
# Added during the CSD deposition process: Sunday 12 April 2020 10:14 AM
# end Validation Reply Form


_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C64 H44 F8 N4 O14'
_chemical_formula_weight         1245.03

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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. 
;

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                   27.197(5)
_cell_length_b                   3.7093(4)
_cell_length_c                   26.924(4)
_cell_angle_alpha                90
_cell_angle_beta                 94.626(16)
_cell_angle_gamma                90
_cell_volume                     2707.3(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    149.9(3)
_cell_measurement_reflns_used    896
_cell_measurement_theta_min      4.0890
_cell_measurement_theta_max      21.3050

_exptl_crystal_description       Parallelepiped
_exptl_crystal_colour            Colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.527
_exptl_crystal_F_000             1280
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.20
_exptl_absorpt_coefficient_mu    0.126
_shelx_estimated_absorpt_T_min   0.940
_shelx_estimated_absorpt_T_max   0.975
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.41500
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
; 
crysalispro 1.171.40.14e (rigaku oxford diffraction, 2018) 
empirical absorption correction using spherical harmonics, 
 implemented in scale3 abspack scaling algorithm. 
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      149.9(3)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed x-ray tube'
_diffrn_measurement_device_type  'xcalibur, sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 16.1048
_diffrn_reflns_number            6515
_diffrn_reflns_av_unetI/netI     0.2805
_diffrn_reflns_av_R_equivalents  0.2222
_diffrn_reflns_limit_h_min       -35
_diffrn_reflns_limit_h_max       34
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_theta_min         3.495
_diffrn_reflns_theta_max         29.105
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.901
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.901
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.901
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             6515
_reflns_number_gt                2742
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
; 
 _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. 
;

_computing_data_collection       'crysalispro 1.171.40.14e (rigaku od, 2018)'
_computing_cell_refinement       'crysalispro 1.171.40.14e (rigaku od, 2018)'
_computing_data_reduction        'crysalispro 1.171.40.14e (rigaku od, 2018)'
_computing_structure_solution    
'SHELXT - G.M.Sheldrick,Acta Crystallogr.A71(2015)3-8.'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    
'ORTEX - P. McArdle, J.Appl.Cryst.,1995,28,65-65.'
_computing_publication_material  
'Oscail - P. McArdle, J.Appl.Cryst.,2017,50,320-326.'
_refine_special_details          
; 
 Refined as a 2-component twin. The crystal was a weak diffracter and was twinned. 
CrysAlisPro 171.40.14e was used to detwin the data and the structure was refined with
ShelxL HKLF 5 BASF 0.29179. Partially overlapped reflections may have contributed to 
detwin difficulties and the high Rint.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+41.6579P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6515
_refine_ls_number_parameters     427
_refine_ls_number_restraints     354
_refine_ls_R_factor_all          0.2978
_refine_ls_R_factor_gt           0.1678
_refine_ls_wR_factor_ref         0.3715
_refine_ls_wR_factor_gt          0.3146
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_restrained_S_all      1.051
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
F1 F -0.1419(5) -0.705(4) -0.1059(4) 0.029(3) Uani 0.494(12) 1 d . . P A 1
F1A F -0.0982(5) -0.256(4) -0.2592(5) 0.036(3) Uani 0.506(12) 1 d . . P A 2
F3 F -0.1704(3) 0.112(2) 0.1290(3) 0.029(2) Uani 0.843(12) 1 d . . P B 3
F3A F -0.2006(14) -0.335(8) -0.0338(13) 0.018(6) Uani 0.157(12) 1 d . . P B 4
F2 F 0.0218(3) -0.610(2) -0.1384(3) 0.050(2) Uani 1 1 d . . . . .
O1 O -0.2807(3) -0.029(2) -0.1094(3) 0.0274(17) Uani 1 1 d . . . . .
H1 H -0.302428 0.050471 -0.093096 0.041 Uiso 1 1 d R U . . .
O2 O -0.3418(3) -0.034(2) -0.1701(3) 0.0304(18) Uani 1 1 d . . . . .
O3 O -0.3244(3) -0.276(2) -0.2575(3) 0.0275(17) Uani 1 1 d . . . . .
H3 H -0.341172 -0.192068 -0.236272 0.041 Uiso 1 1 d R U . . .
C1 C -0.2621(4) -0.242(3) -0.1883(3) 0.0163(16) Uani 1 1 d . . . . .
C2 C -0.2778(4) -0.333(2) -0.2378(4) 0.0162(16) Uani 1 1 d . . . . .
C3 C -0.2442(4) -0.479(3) -0.2679(4) 0.0175(17) Uani 1 1 d . . . . .
H3A H -0.254455 -0.541690 -0.300543 0.021 Uiso 1 1 calc R U . . .
C4 C -0.1955(4) -0.535(2) -0.2502(3) 0.0152(16) Uani 1 1 d . . . . .
H4 H -0.173490 -0.639709 -0.270671 0.018 Uiso 1 1 calc R U . . .
C5 C -0.1796(4) -0.434(3) -0.2020(4) 0.0164(16) Uani 1 1 d . . . . .
C6 C -0.2129(4) -0.304(2) -0.1714(4) 0.0156(16) Uani 1 1 d . . . . .
H6 H -0.202640 -0.254025 -0.138308 0.019 Uiso 1 1 calc R U . . .
C7 C -0.1256(4) -0.484(3) -0.1850(4) 0.0181(16) Uani 1 1 d . . . . .
C8 C -0.0892(4) -0.391(3) -0.2139(4) 0.028(2) Uani 1 1 d . . . . .
H8 H -0.098342 -0.289469 -0.244832 0.033 Uiso 0.5 1 calc R U P A 1
C9 C -0.0396(5) -0.435(3) -0.2010(5) 0.034(2) Uani 1 1 d . . . . .
H9A H -0.015957 -0.384924 -0.223163 0.040 Uiso 1 1 calc R U . . .
C10 C -0.0265(5) -0.561(3) -0.1520(5) 0.035(2) Uani 1 1 d . . . . .
C11 C -0.0616(4) -0.656(3) -0.1213(5) 0.0273(19) Uani 1 1 d . . . . .
H11 H -0.052813 -0.748837 -0.089746 0.033 Uiso 1 1 calc R U . . .
C12 C -0.1103(4) -0.611(3) -0.1377(4) 0.0201(17) Uani 1 1 d . . . . .
H12 H -0.134251 -0.668733 -0.116165 0.024 Uiso 0.5 1 calc R U P A 2
C13 C -0.2984(4) -0.094(2) -0.1553(4) 0.0155(16) Uani 1 1 d . . . . .
F4 F -0.0416(3) 0.016(2) 0.0269(3) 0.057(2) Uani 1 1 d . . . . .
O4 O -0.3513(3) 0.210(2) -0.0571(2) 0.0250(17) Uani 1 1 d . . . . .
H4A H -0.376300 0.266761 -0.074395 0.038 Uiso 1 1 d R U . . .
O5 O -0.4107(3) 0.064(2) -0.0091(2) 0.0232(15) Uani 1 1 d . . . . .
O6 O -0.3924(3) -0.219(2) 0.0741(3) 0.0230(16) Uani 1 1 d . . . . .
H6A H -0.407869 -0.137637 0.049234 0.035 Uiso 1 1 d R U . . .
C14 C -0.3281(4) -0.040(2) 0.0224(3) 0.0132(15) Uani 1 1 d . . . . .
C15 C -0.3440(4) -0.191(3) 0.0669(3) 0.0156(17) Uani 1 1 d . . . . .
C16 C -0.3088(4) -0.306(3) 0.1042(4) 0.0175(18) Uani 1 1 d . . . . .
H16 H -0.319036 -0.400384 0.133650 0.021 Uiso 1 1 calc R U . . .
C17 C -0.2587(4) -0.283(3) 0.0977(3) 0.0155(17) Uani 1 1 d . . . . .
H17 H -0.235737 -0.363262 0.122679 0.019 Uiso 1 1 calc R U . . .
C18 C -0.2425(4) -0.138(3) 0.0537(3) 0.0156(16) Uani 1 1 d . . . . .
C19 C -0.2782(4) -0.018(2) 0.0164(3) 0.0145(16) Uani 1 1 d . . . . .
H19 H -0.267847 0.078768 -0.012854 0.017 Uiso 1 1 calc R U . . .
C20 C -0.1895(4) -0.103(3) 0.0470(4) 0.0189(16) Uani 1 1 d . . . . .
C21 C -0.1555(4) 0.023(3) 0.0846(4) 0.0219(19) Uani 1 1 d . . . . .
H21 H -0.167071 0.086075 0.115018 0.026 Uiso 0.2 1 calc R U P B 4
C22 C -0.1054(4) 0.060(3) 0.0793(5) 0.030(2) Uani 1 1 d . . . . .
H22 H -0.083488 0.138330 0.105427 0.036 Uiso 1 1 calc R U . . .
C23 C -0.0897(4) -0.027(3) 0.0331(4) 0.029(2) Uani 1 1 d . . . . .
C24 C -0.1214(4) -0.155(3) -0.0055(5) 0.031(2) Uani 1 1 d . . . . .
H24 H -0.110165 -0.215912 -0.036066 0.037 Uiso 1 1 calc R U . . .
C25 C -0.1704(4) -0.188(3) 0.0031(4) 0.0204(18) Uani 1 1 d . . . . .
H25 H -0.192000 -0.273764 -0.022736 0.024 Uiso 0.8 1 calc R U P B 3
C26 C -0.3660(4) 0.083(3) -0.0173(3) 0.0160(17) Uani 1 1 d . . . . .
O7 O -0.4276(3) 0.416(2) 0.2365(3) 0.0243(16) Uani 1 1 d . . . . .
N1 N -0.5679(3) 0.556(2) 0.1095(3) 0.0216(17) Uani 1 1 d . . . . .
N2 N -0.3969(3) 0.132(2) 0.1713(3) 0.0196(18) Uani 1 1 d . . . . .
H2A H -0.370021 0.085239 0.189090 0.024 Uiso 1 1 d R U . . .
H2B H -0.400351 0.066329 0.140560 0.024 Uiso 1 1 d R U . . .
C27 C -0.5282(4) 0.470(3) 0.0845(4) 0.023(2) Uani 1 1 d . . . . .
H27 H -0.531019 0.472539 0.049883 0.028 Uiso 1 1 calc R U . . .
C28 C -0.4829(4) 0.378(3) 0.1101(4) 0.022(2) Uani 1 1 d . . . . .
H28 H -0.455877 0.316170 0.092787 0.026 Uiso 1 1 calc R U . . .
C29 C -0.4795(4) 0.381(2) 0.1611(3) 0.0153(16) Uani 1 1 d . . . . .
C30 C -0.5204(4) 0.469(3) 0.1870(4) 0.0188(18) Uani 1 1 d . . . . .
H30 H -0.518526 0.467568 0.221619 0.023 Uiso 1 1 calc R U . . .
C31 C -0.5642(4) 0.560(3) 0.1591(4) 0.0213(19) Uani 1 1 d . . . . .
H31 H -0.591543 0.624339 0.175631 0.026 Uiso 1 1 calc R U . . .
C32 C -0.4321(4) 0.315(3) 0.1936(4) 0.0171(17) Uani 1 1 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
F1 C12 1.309(16) . ?
F1A C8 1.323(16) . ?
F3 C21 1.334(12) . ?
F3A C25 1.35(4) . ?
F2 C10 1.345(14) . ?
O1 C13 1.311(12) . ?
O1 H1 0.8191 . ?
O2 C13 1.234(13) . ?
O3 C2 1.349(12) . ?
O3 H3 0.8220 . ?
C1 C6 1.396(14) . ?
C1 C2 1.407(13) . ?
C1 C13 1.488(13) . ?
C2 C3 1.379(13) . ?
C3 C4 1.388(14) . ?
C3 H3A 0.9300 . ?
C4 C5 1.385(13) . ?
C4 H4 0.9300 . ?
C5 C6 1.363(13) . ?
C5 C7 1.514(15) . ?
C6 H6 0.9300 . ?
C7 C8 1.352(14) . ?
C7 C12 1.391(14) . ?
C8 C9 1.375(16) . ?
C8 H8 0.9300 . ?
C9 C10 1.417(17) . ?
C9 H9A 0.9300 . ?
C10 C11 1.361(16) . ?
C11 C12 1.373(15) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
F4 C23 1.341(13) . ?
O4 C26 1.264(11) . ?
O4 H4A 0.8200 . ?
O5 C26 1.256(12) . ?
O6 C15 1.350(12) . ?
O6 H6A 0.8199 . ?
C14 C19 1.384(14) . ?
C14 C15 1.420(13) . ?
C14 C26 1.495(14) . ?
C15 C16 1.396(13) . ?
C16 C17 1.391(14) . ?
C16 H16 0.9300 . ?
C17 C18 1.404(13) . ?
C17 H17 0.9300 . ?
C18 C19 1.409(13) . ?
C18 C20 1.472(14) . ?
C19 H19 0.9300 . ?
C20 C25 1.365(14) . ?
C20 C21 1.397(15) . ?
C21 C22 1.389(15) . ?
C21 H21 0.9300 . ?
C22 C23 1.386(16) . ?
C22 H22 0.9300 . ?
C23 C24 1.380(16) . ?
C24 C25 1.376(15) . ?
C24 H24 0.9300 . ?
C25 H25 0.9300 . ?
O7 C32 1.211(11) . ?
N1 C31 1.331(12) . ?
N1 C27 1.354(13) . ?
N2 C32 1.353(13) . ?
N2 H2A 0.8600 . ?
N2 H2B 0.8599 . ?
C27 C28 1.405(15) . ?
C27 H27 0.9300 . ?
C28 C29 1.370(13) . ?
C28 H28 0.9300 . ?
C29 C30 1.398(13) . ?
C29 C32 1.517(14) . ?
C30 C31 1.397(15) . ?
C30 H30 0.9300 . ?
C31 H31 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
C13 O1 H1 110.2 . . ?
C2 O3 H3 110.1 . . ?
C6 C1 C2 118.7(9) . . ?
C6 C1 C13 122.0(9) . . ?
C2 C1 C13 119.3(10) . . ?
O3 C2 C3 118.4(9) . . ?
O3 C2 C1 122.6(9) . . ?
C3 C2 C1 119.0(10) . . ?
C2 C3 C4 121.1(9) . . ?
C2 C3 H3A 119.5 . . ?
C4 C3 H3A 119.5 . . ?
C5 C4 C3 119.9(9) . . ?
C5 C4 H4 120.1 . . ?
C3 C4 H4 120.1 . . ?
C6 C5 C4 119.4(10) . . ?
C6 C5 C7 122.4(9) . . ?
C4 C5 C7 118.2(8) . . ?
C5 C6 C1 121.8(9) . . ?
C5 C6 H6 119.1 . . ?
C1 C6 H6 119.1 . . ?
C8 C7 C12 115.8(11) . . ?
C8 C7 C5 122.2(10) . . ?
C12 C7 C5 121.9(9) . . ?
F1A C8 C7 122.4(12) . . ?
F1A C8 C9 112.5(11) . . ?
C7 C8 C9 125.0(11) . . ?
C7 C8 H8 117.5 . . ?
C9 C8 H8 117.5 . . ?
C8 C9 C10 116.2(11) . . ?
C8 C9 H9A 121.9 . . ?
C10 C9 H9A 121.9 . . ?
F2 C10 C11 121.1(12) . . ?
F2 C10 C9 117.7(11) . . ?
C11 C10 C9 121.0(12) . . ?
C10 C11 C12 118.7(11) . . ?
C10 C11 H11 120.6 . . ?
C12 C11 H11 120.6 . . ?
F1 C12 C11 115.1(11) . . ?
F1 C12 C7 121.8(11) . . ?
C11 C12 C7 123.0(11) . . ?
C11 C12 H12 118.5 . . ?
C7 C12 H12 118.5 . . ?
O2 C13 O1 122.8(9) . . ?
O2 C13 C1 122.4(9) . . ?
O1 C13 C1 114.8(9) . . ?
C26 O4 H4A 105.9 . . ?
C15 O6 H6A 107.3 . . ?
C19 C14 C15 119.3(9) . . ?
C19 C14 C26 121.7(8) . . ?
C15 C14 C26 119.0(9) . . ?
O6 C15 C16 119.5(9) . . ?
O6 C15 C14 121.2(9) . . ?
C16 C15 C14 119.3(9) . . ?
C17 C16 C15 120.8(9) . . ?
C17 C16 H16 119.6 . . ?
C15 C16 H16 119.6 . . ?
C16 C17 C18 120.5(9) . . ?
C16 C17 H17 119.7 . . ?
C18 C17 H17 119.7 . . ?
C17 C18 C19 118.4(10) . . ?
C17 C18 C20 120.9(9) . . ?
C19 C18 C20 120.7(9) . . ?
C14 C19 C18 121.6(9) . . ?
C14 C19 H19 119.2 . . ?
C18 C19 H19 119.2 . . ?
C25 C20 C21 115.4(10) . . ?
C25 C20 C18 122.0(10) . . ?
C21 C20 C18 122.6(9) . . ?
F3 C21 C22 116.0(10) . . ?
F3 C21 C20 120.2(10) . . ?
C22 C21 C20 123.8(10) . . ?
C22 C21 H21 118.1 . . ?
C20 C21 H21 118.1 . . ?
C23 C22 C21 116.5(11) . . ?
C23 C22 H22 121.8 . . ?
C21 C22 H22 121.8 . . ?
F4 C23 C24 120.3(10) . . ?
F4 C23 C22 117.3(11) . . ?
C24 C23 C22 122.4(11) . . ?
C25 C24 C23 117.4(11) . . ?
C25 C24 H24 121.3 . . ?
C23 C24 H24 121.3 . . ?
F3A C25 C20 118.7(18) . . ?
F3A C25 C24 116.7(18) . . ?
C20 C25 C24 124.5(11) . . ?
C20 C25 H25 117.8 . . ?
C24 C25 H25 117.8 . . ?
O5 C26 O4 123.2(9) . . ?
O5 C26 C14 118.5(8) . . ?
O4 C26 C14 118.3(9) . . ?
C31 N1 C27 120.0(9) . . ?
C32 N2 H2A 117.0 . . ?
C32 N2 H2B 123.0 . . ?
H2A N2 H2B 120.0 . . ?
N1 C27 C28 121.2(9) . . ?
N1 C27 H27 119.4 . . ?
C28 C27 H27 119.4 . . ?
C29 C28 C27 118.4(10) . . ?
C29 C28 H28 120.8 . . ?
C27 C28 H28 120.8 . . ?
C28 C29 C30 120.6(10) . . ?
C28 C29 C32 124.2(9) . . ?
C30 C29 C32 115.1(9) . . ?
C31 C30 C29 117.8(9) . . ?
C31 C30 H30 121.1 . . ?
C29 C30 H30 121.1 . . ?
N1 C31 C30 122.0(10) . . ?
N1 C31 H31 119.0 . . ?
C30 C31 H31 119.0 . . ?
O7 C32 N2 124.0(10) . . ?
O7 C32 C29 120.9(9) . . ?
N2 C32 C29 115.0(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
C6 C1 C2 O3 -178.7(9) . . . . ?
C13 C1 C2 O3 3.3(14) . . . . ?
C6 C1 C2 C3 -0.2(14) . . . . ?
C13 C1 C2 C3 -178.2(9) . . . . ?
O3 C2 C3 C4 178.2(9) . . . . ?
C1 C2 C3 C4 -0.4(14) . . . . ?
C2 C3 C4 C5 -1.7(14) . . . . ?
C3 C4 C5 C6 4.3(14) . . . . ?
C3 C4 C5 C7 -177.2(9) . . . . ?
C4 C5 C6 C1 -5.0(15) . . . . ?
C7 C5 C6 C1 176.6(9) . . . . ?
C2 C1 C6 C5 2.9(14) . . . . ?
C13 C1 C6 C5 -179.1(9) . . . . ?
C6 C5 C7 C8 -137.3(11) . . . . ?
C4 C5 C7 C8 44.2(14) . . . . ?
C6 C5 C7 C12 39.5(14) . . . . ?
C4 C5 C7 C12 -139.0(10) . . . . ?
C12 C7 C8 F1A -178.0(12) . . . . ?
C5 C7 C8 F1A -1.1(18) . . . . ?
C12 C7 C8 C9 4.3(16) . . . . ?
C5 C7 C8 C9 -178.7(10) . . . . ?
F1A C8 C9 C10 176.9(11) . . . . ?
C7 C8 C9 C10 -5.2(18) . . . . ?
C8 C9 C10 F2 179.5(10) . . . . ?
C8 C9 C10 C11 4.4(17) . . . . ?
F2 C10 C11 C12 -177.9(10) . . . . ?
C9 C10 C11 C12 -3.0(17) . . . . ?
C10 C11 C12 F1 -179.5(11) . . . . ?
C10 C11 C12 C7 2.0(16) . . . . ?
C8 C7 C12 F1 179.1(11) . . . . ?
C5 C7 C12 F1 2.1(16) . . . . ?
C8 C7 C12 C11 -2.6(15) . . . . ?
C5 C7 C12 C11 -179.5(9) . . . . ?
C6 C1 C13 O2 178.9(9) . . . . ?
C2 C1 C13 O2 -3.1(14) . . . . ?
C6 C1 C13 O1 -0.3(13) . . . . ?
C2 C1 C13 O1 177.6(9) . . . . ?
C19 C14 C15 O6 -179.6(9) . . . . ?
C26 C14 C15 O6 -0.8(14) . . . . ?
C19 C14 C15 C16 1.2(14) . . . . ?
C26 C14 C15 C16 179.9(9) . . . . ?
O6 C15 C16 C17 179.5(9) . . . . ?
C14 C15 C16 C17 -1.3(15) . . . . ?
C15 C16 C17 C18 0.7(15) . . . . ?
C16 C17 C18 C19 0.0(14) . . . . ?
C16 C17 C18 C20 178.4(9) . . . . ?
C15 C14 C19 C18 -0.5(14) . . . . ?
C26 C14 C19 C18 -179.2(9) . . . . ?
C17 C18 C19 C14 -0.1(14) . . . . ?
C20 C18 C19 C14 -178.5(9) . . . . ?
C17 C18 C20 C25 137.7(10) . . . . ?
C19 C18 C20 C25 -43.9(14) . . . . ?
C17 C18 C20 C21 -43.4(14) . . . . ?
C19 C18 C20 C21 135.0(10) . . . . ?
C25 C20 C21 F3 -179.9(9) . . . . ?
C18 C20 C21 F3 1.1(16) . . . . ?
C25 C20 C21 C22 -0.7(16) . . . . ?
C18 C20 C21 C22 -179.7(10) . . . . ?
F3 C21 C22 C23 -179.0(10) . . . . ?
C20 C21 C22 C23 1.9(17) . . . . ?
C21 C22 C23 F4 178.5(10) . . . . ?
C21 C22 C23 C24 -2.2(18) . . . . ?
F4 C23 C24 C25 -179.3(10) . . . . ?
C22 C23 C24 C25 1.3(17) . . . . ?
C21 C20 C25 F3A 175.6(18) . . . . ?
C18 C20 C25 F3A -5(2) . . . . ?
C21 C20 C25 C24 -0.3(16) . . . . ?
C18 C20 C25 C24 178.8(10) . . . . ?
C23 C24 C25 F3A -176.0(18) . . . . ?
C23 C24 C25 C20 0.0(17) . . . . ?
C19 C14 C26 O5 -178.1(9) . . . . ?
C15 C14 C26 O5 3.2(13) . . . . ?
C19 C14 C26 O4 0.0(14) . . . . ?
C15 C14 C26 O4 -178.7(9) . . . . ?
C31 N1 C27 C28 1.1(16) . . . . ?
N1 C27 C28 C29 -0.8(16) . . . . ?
C27 C28 C29 C30 0.9(15) . . . . ?
C27 C28 C29 C32 -175.2(9) . . . . ?
C28 C29 C30 C31 -1.1(15) . . . . ?
C32 C29 C30 C31 175.2(9) . . . . ?
C27 N1 C31 C30 -1.4(16) . . . . ?
C29 C30 C31 N1 1.4(15) . . . . ?
C28 C29 C32 O7 159.2(10) . . . . ?
C30 C29 C32 O7 -17.0(14) . . . . ?
C28 C29 C32 N2 -22.1(14) . . . . ?
C30 C29 C32 N2 161.7(9) . . . . ?

_refine_diff_density_max         0.580
_refine_diff_density_min         -0.693
_refine_diff_density_rms         0.147

####################################################################### 
# 
# 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_dif_ebipy
_database_code_depnum_ccdc_archive 'CCDC 1982622'
loop_
_audit_author_name
_audit_author_address
'Patrick McArdle'
;NUI, Galway
Republic of Ireland
;
_audit_update_record             
;
2020-04-07 deposited with the CCDC.	2020-04-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H13 F2 N O3'
_chemical_formula_weight         341.30

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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. 
;

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                   3.8999(2)
_cell_length_b                   34.7661(18)
_cell_length_c                   11.4896(7)
_cell_angle_alpha                90
_cell_angle_beta                 94.404(5)
_cell_angle_gamma                90
_cell_volume                     1553.21(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    299.0(1)
_cell_measurement_reflns_used    2225
_cell_measurement_theta_min      3.7550
_cell_measurement_theta_max      28.7770

_exptl_crystal_description       Parallelepiped
_exptl_crystal_colour            Colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.460
_exptl_crystal_F_000             704
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.04
_exptl_absorpt_coefficient_mu    0.115
_shelx_estimated_absorpt_T_min   0.945
_shelx_estimated_absorpt_T_max   0.995
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.80654
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
; 
crysalispro 1.171.40.14e (rigaku oxford diffraction, 2018) 
empirical absorption correction using spherical harmonics, 
 implemented in scale3 abspack scaling algorithm. 
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      299.0(1)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed x-ray tube'
_diffrn_measurement_device_type  'xcalibur, sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 16.1048
_diffrn_reflns_number            6841
_diffrn_reflns_av_unetI/netI     0.0451
_diffrn_reflns_av_R_equivalents  0.0253
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -39
_diffrn_reflns_limit_k_max       44
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.516
_diffrn_reflns_theta_max         27.499
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.965
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.965
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.965
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3426
_reflns_number_gt                2413
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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. 
;

_computing_data_collection       'crysalispro 1.171.40.14e (rigaku od, 2018)'
_computing_cell_refinement       'crysalispro 1.171.40.14e (rigaku od, 2018)'
_computing_data_reduction        'crysalispro 1.171.40.14e (rigaku od, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    
'ORTEX - P. McArdle, J.Appl.Cryst.,1995,28,65-65.'
_computing_publication_material  
'Oscail - P. McArdle, J.Appl.Cryst.,2017,50,320-326.'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0459P)²+0.1883P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.0058(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3426
_refine_ls_number_parameters     245
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0769
_refine_ls_R_factor_gt           0.0509
_refine_ls_wR_factor_ref         0.1293
_refine_ls_wR_factor_gt          0.1120
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_restrained_S_all      1.049
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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
F1 F 0.9933(4) 0.84557(3) 0.30930(15) 0.0916(5) Uani 1 1 d . . . . .
F2A F 0.4952(5) 0.74696(5) 0.08723(14) 0.0708(6) Uani 0.762(3) 1 d . . P A 1
F2B F 1.1190(14) 0.72056(13) 0.4403(4) 0.0558(17) Uani 0.238(3) 1 d . . P A 2
O1 O 0.5708(5) 0.57121(4) 0.19275(16) 0.0743(5) Uani 1 1 d D . . . .
O2 O 0.4366(5) 0.56664(4) 0.40550(14) 0.0739(5) Uani 1 1 d . . . . .
O3 O 0.4747(5) 0.61835(4) 0.51896(13) 0.0627(5) Uani 1 1 d D . . . .
N1 N 0.3049(5) 0.57194(4) 0.67962(15) 0.0493(4) Uani 1 1 d . . . . .
C1 C 0.9350(6) 0.80750(6) 0.2928(2) 0.0563(6) Uani 1 1 d . . . . .
C2 C 1.0676(5) 0.78248(6) 0.37585(19) 0.0491(5) Uani 1 1 d . . . . .
H2 H 1.198610 0.791217 0.441613 0.064 Uiso 1 1 calc R U . . .
C3 C 1.0015(5) 0.74389(5) 0.35935(16) 0.0407(4) Uani 1 1 d . . . . .
H3A H 1.088879 0.726643 0.415965 0.053 Uiso 0.762(3) 1 calc R U P A 1
C4 C 0.8104(5) 0.72957(5) 0.26213(15) 0.0377(4) Uani 1 1 d . . . . .
C5 C 0.6879(5) 0.75731(6) 0.18165(17) 0.0479(5) Uani 1 1 d . . . . .
H5 H 0.559204 0.749007 0.114858 0.062 Uiso 0.238(3) 1 calc R U P A 2
C6 C 0.7449(6) 0.79602(6) 0.1947(2) 0.0568(6) Uani 1 1 d . . . . .
H6 H 0.657741 0.813629 0.139148 0.074 Uiso 1 1 calc R U . . .
C7 C 0.7435(5) 0.68805(5) 0.24539(15) 0.0375(4) Uani 1 1 d . . . . .
C8 C 0.7740(5) 0.67052(6) 0.13776(17) 0.0500(5) Uani 1 1 d . . . . .
H8 H 0.832426 0.685420 0.075043 0.065 Uiso 1 1 calc R U . . .
C9 C 0.7201(6) 0.63189(6) 0.12186(19) 0.0576(6) Uani 1 1 d . . . . .
H9 H 0.745539 0.620898 0.049232 0.075 Uiso 1 1 calc R U . . .
C10 C 0.6282(6) 0.60914(6) 0.21309(18) 0.0499(5) Uani 1 1 d . . . . .
C11 C 0.5950(5) 0.62565(5) 0.32221(16) 0.0408(4) Uani 1 1 d . . . . .
C12 C 0.6565(5) 0.66483(5) 0.33647(15) 0.0383(4) Uani 1 1 d . . . . .
H12 H 0.638581 0.675795 0.409591 0.050 Uiso 1 1 calc R U . . .
C13 C 0.4975(6) 0.60135(6) 0.42014(19) 0.0499(5) Uani 1 1 d . . . . .
C14 C 0.1490(6) 0.53883(6) 0.65312(18) 0.0549(6) Uani 1 1 d . . . . .
H14 H 0.105640 0.532305 0.574881 0.071 Uiso 1 1 calc R U . . .
C15 C 0.0486(6) 0.51364(5) 0.73704(17) 0.0489(5) Uani 1 1 d . . . . .
H15 H -0.057653 0.490545 0.714865 0.064 Uiso 1 1 calc R U . . .
C16 C 0.3676(5) 0.58074(5) 0.79187(18) 0.0471(5) Uani 1 1 d . . . . .
H16 H 0.480316 0.603701 0.811256 0.061 Uiso 1 1 calc R U . . .
C17 C 0.2731(5) 0.55736(5) 0.88060(17) 0.0432(5) Uani 1 1 d . . . . .
H17 H 0.320777 0.564673 0.958012 0.056 Uiso 1 1 calc R U . . .
C18 C 0.1062(5) 0.52278(5) 0.85408(16) 0.0378(4) Uani 1 1 d . . . . .
C19 C -0.0067(5) 0.49651(5) 0.94343(15) 0.0408(5) Uani 1 1 d . . . . .
H19 H -0.095569 0.472861 0.918136 0.053 Uiso 1 1 calc R U . . .
H1 H 0.510(8) 0.5637(8) 0.2646(18) 0.110(11) Uiso 1 1 d D . . . .
H3 H 0.419(8) 0.6002(8) 0.579(2) 0.140(12) 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
F1 C1 1.354(2) . ?
F2A C5 1.321(3) . ?
F2B C3 1.291(5) . ?
O1 C10 1.355(2) . ?
O1 H1 0.915(17) . ?
O2 C13 1.239(2) . ?
O3 C13 1.289(2) . ?
O3 H3 0.969(18) . ?
N1 C14 1.326(3) . ?
N1 C16 1.330(2) . ?
C1 C6 1.360(3) . ?
C1 C2 1.363(3) . ?
C2 C3 1.377(2) . ?
C2 H2 0.9300 . ?
C3 C4 1.387(3) . ?
C3 H3A 0.9300 . ?
C4 C5 1.395(3) . ?
C4 C7 1.477(2) . ?
C5 C6 1.371(3) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 C12 1.384(2) . ?
C7 C8 1.392(3) . ?
C8 C9 1.369(3) . ?
C8 H8 0.9300 . ?
C9 C10 1.382(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.394(3) . ?
C11 C12 1.391(2) . ?
C11 C13 1.480(3) . ?
C12 H12 0.9300 . ?
C14 C15 1.381(3) . ?
C14 H14 0.9300 . ?
C15 C18 1.383(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.376(2) . ?
C16 H16 0.9300 . ?
C17 C18 1.390(2) . ?
C17 H17 0.9300 . ?
C18 C19 1.467(2) . ?
C19 C19 1.319(3) 3_567 ?
C19 H19 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 O1 H1 100.0(18) . . ?
C13 O3 H3 111.0(19) . . ?
C14 N1 C16 117.99(16) . . ?
F1 C1 C6 118.5(2) . . ?
F1 C1 C2 118.4(2) . . ?
C6 C1 C2 123.1(2) . . ?
C1 C2 C3 117.9(2) . . ?
C1 C2 H2 121.0 . . ?
C3 C2 H2 121.0 . . ?
F2B C3 C2 117.4(3) . . ?
F2B C3 C4 119.6(3) . . ?
C2 C3 C4 122.97(19) . . ?
C2 C3 H3A 118.5 . . ?
C4 C3 H3A 118.5 . . ?
C3 C4 C5 114.93(18) . . ?
C3 C4 C7 122.30(17) . . ?
C5 C4 C7 122.77(18) . . ?
F2A C5 C6 115.78(19) . . ?
F2A C5 C4 120.02(19) . . ?
C6 C5 C4 124.2(2) . . ?
C6 C5 H5 117.9 . . ?
C4 C5 H5 117.9 . . ?
C1 C6 C5 116.9(2) . . ?
C1 C6 H6 121.5 . . ?
C5 C6 H6 121.5 . . ?
C12 C7 C8 117.31(17) . . ?
C12 C7 C4 121.51(16) . . ?
C8 C7 C4 121.16(16) . . ?
C9 C8 C7 121.69(18) . . ?
C9 C8 H8 119.2 . . ?
C7 C8 H8 119.2 . . ?
C8 C9 C10 120.40(19) . . ?
C8 C9 H9 119.8 . . ?
C10 C9 H9 119.8 . . ?
O1 C10 C9 118.37(19) . . ?
O1 C10 C11 122.03(18) . . ?
C9 C10 C11 119.60(18) . . ?
C12 C11 C10 118.83(16) . . ?
C12 C11 C13 121.45(17) . . ?
C10 C11 C13 119.72(17) . . ?
C7 C12 C11 122.15(17) . . ?
C7 C12 H12 118.9 . . ?
C11 C12 H12 118.9 . . ?
O2 C13 O3 122.74(18) . . ?
O2 C13 C11 120.71(19) . . ?
O3 C13 C11 116.53(17) . . ?
N1 C14 C15 122.7(2) . . ?
N1 C14 H14 118.7 . . ?
C15 C14 H14 118.7 . . ?
C14 C15 C18 119.96(19) . . ?
C14 C15 H15 120.0 . . ?
C18 C15 H15 120.0 . . ?
N1 C16 C17 122.88(19) . . ?
N1 C16 H16 118.6 . . ?
C17 C16 H16 118.6 . . ?
C16 C17 C18 119.75(19) . . ?
C16 C17 H17 120.1 . . ?
C18 C17 H17 120.1 . . ?
C15 C18 C17 116.75(16) . . ?
C15 C18 C19 120.16(17) . . ?
C17 C18 C19 123.09(17) . . ?
C19 C19 C18 125.7(2) 3_567 . ?
C19 C19 H19 117.1 3_567 . ?
C18 C19 H19 117.1 . . ?

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
F1 C1 C2 C3 178.80(17) . . . . ?
C6 C1 C2 C3 -0.7(3) . . . . ?
C1 C2 C3 F2B -177.9(3) . . . . ?
C1 C2 C3 C4 0.7(3) . . . . ?
F2B C3 C4 C5 178.3(3) . . . . ?
C2 C3 C4 C5 -0.2(3) . . . . ?
F2B C3 C4 C7 -1.9(4) . . . . ?
C2 C3 C4 C7 179.63(16) . . . . ?
C3 C4 C5 F2A -178.24(18) . . . . ?
C7 C4 C5 F2A 1.9(3) . . . . ?
C3 C4 C5 C6 -0.3(3) . . . . ?
C7 C4 C5 C6 179.88(18) . . . . ?
F1 C1 C6 C5 -179.25(17) . . . . ?
C2 C1 C6 C5 0.2(3) . . . . ?
F2A C5 C6 C1 178.33(19) . . . . ?
C4 C5 C6 C1 0.3(3) . . . . ?
C3 C4 C7 C12 42.5(3) . . . . ?
C5 C4 C7 C12 -137.67(19) . . . . ?
C3 C4 C7 C8 -135.9(2) . . . . ?
C5 C4 C7 C8 44.0(3) . . . . ?
C12 C7 C8 C9 0.1(3) . . . . ?
C4 C7 C8 C9 178.5(2) . . . . ?
C7 C8 C9 C10 0.9(4) . . . . ?
C8 C9 C10 O1 178.7(2) . . . . ?
C8 C9 C10 C11 -0.9(4) . . . . ?
O1 C10 C11 C12 -179.70(19) . . . . ?
C9 C10 C11 C12 -0.1(3) . . . . ?
O1 C10 C11 C13 0.6(3) . . . . ?
C9 C10 C11 C13 -179.8(2) . . . . ?
C8 C7 C12 C11 -1.1(3) . . . . ?
C4 C7 C12 C11 -179.57(17) . . . . ?
C10 C11 C12 C7 1.2(3) . . . . ?
C13 C11 C12 C7 -179.14(18) . . . . ?
C12 C11 C13 O2 178.5(2) . . . . ?
C10 C11 C13 O2 -1.8(3) . . . . ?
C12 C11 C13 O3 -0.4(3) . . . . ?
C10 C11 C13 O3 179.3(2) . . . . ?
C16 N1 C14 C15 0.5(3) . . . . ?
N1 C14 C15 C18 0.8(3) . . . . ?
C14 N1 C16 C17 -1.1(3) . . . . ?
N1 C16 C17 C18 0.4(3) . . . . ?
C14 C15 C18 C17 -1.4(3) . . . . ?
C14 C15 C18 C19 178.67(19) . . . . ?
C16 C17 C18 C15 0.9(3) . . . . ?
C16 C17 C18 C19 -179.20(18) . . . . ?
C15 C18 C19 C19 -173.8(2) . . . 3_567 ?
C17 C18 C19 C19 6.3(4) . . . 3_567 ?

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
C2 H2 F2A^a 0.93 2.37 3.018(3) 126.8 2_665 yes
C3 H3A^a F2A^a 0.93 2.60 3.145(3) 118.1 2_665 yes
O1 H1 O2 0.915(17) 1.668(19) 2.544(2) 159(3) . yes
O3 H3 N1 0.969(18) 1.609(18) 2.5764(19) 176(3) . yes

_refine_diff_density_max         0.183
_refine_diff_density_min         -0.155
_refine_diff_density_rms         0.035

####################################################################### 
# 
# 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_dif_bipy
_database_code_depnum_ccdc_archive 'CCDC 1982621'
loop_
_audit_author_name
_audit_author_address
'Patrick McArdle'
;NUI, Galway
Republic of Ireland
;
_audit_update_record             
;
2020-04-07 deposited with the CCDC.	2020-04-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C36 H24 F4 N2 O6'
_chemical_formula_weight         656.57

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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. 
;

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                   3.7762(4)
_cell_length_b                   29.2094(16)
_cell_length_c                   13.5261(9)
_cell_angle_alpha                90
_cell_angle_beta                 96.309(7)
_cell_angle_gamma                90
_cell_volume                     1482.9(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    299.0(1)
_cell_measurement_reflns_used    1088
_cell_measurement_theta_min      4.4390
_cell_measurement_theta_max      27.5140

_exptl_crystal_description       Parallelepiped
_exptl_crystal_colour            Colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.470
_exptl_crystal_F_000             676
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.20
_exptl_absorpt_coefficient_mu    0.117
_shelx_estimated_absorpt_T_min   0.944
_shelx_estimated_absorpt_T_max   0.977
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.92784
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
; 
crysalispro 1.171.40.14e (rigaku oxford diffraction, 2018) 
empirical absorption correction using spherical harmonics, 
 implemented in scale3 abspack scaling algorithm. 
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      299.0(1)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed x-ray tube'
_diffrn_measurement_device_type  'xcalibur, sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 16.1048
_diffrn_reflns_number            6756
_diffrn_reflns_av_unetI/netI     0.0577
_diffrn_reflns_av_R_equivalents  0.0278
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -39
_diffrn_reflns_limit_k_max       36
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.683
_diffrn_reflns_theta_max         29.151
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.852
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.852
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.852
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             3407
_reflns_number_gt                1933
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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. 
;

_computing_data_collection       'crysalispro 1.171.40.14e (rigaku od, 2018)'
_computing_cell_refinement       'crysalispro 1.171.40.14e (rigaku od, 2018)'
_computing_data_reduction        'crysalispro 1.171.40.14e (rigaku od, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    
'ORTEX - P. McArdle, J.Appl.Cryst.,1995,28,65-65.'
_computing_publication_material  
'Oscail - P. McArdle, J.Appl.Cryst.,2017,50,320-326.'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0449P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3407
_refine_ls_number_parameters     279
_refine_ls_number_restraints     68
_refine_ls_R_factor_all          0.1097
_refine_ls_R_factor_gt           0.0521
_refine_ls_wR_factor_ref         0.1175
_refine_ls_wR_factor_gt          0.0957
_refine_ls_goodness_of_fit_ref   0.998
_refine_ls_restrained_S_all      0.991
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
F1 F 0.7735(5) 0.03556(4) 0.37811(10) 0.0867(5) Uani 1 1 d . . . . .
F2 F 0.7428(4) 0.08186(4) 0.70701(9) 0.0673(4) Uani 1 1 d . . . . .
O1 O 1.0562(5) 0.27889(5) 0.87443(11) 0.0682(5) Uani 1 1 d D . . . .
O2 O 0.7461(5) 0.33148(5) 0.73720(11) 0.0729(5) Uani 1 1 d . . . . .
O3 O 0.5548(5) 0.30237(5) 0.58953(11) 0.0616(5) Uani 1 1 d D . . . .
N1 N 0.352(3) 0.3887(4) 0.5494(9) 0.044(2) Uani 0.5 1 d D U P A 1
C1 C 0.8273(7) 0.06858(6) 0.44901(16) 0.0538(6) Uani 1 1 d . . . . .
C2 C 0.9397(6) 0.11082(7) 0.42256(15) 0.0514(6) Uani 1 1 d . . . . .
H2 H 0.983195 0.116997 0.357535 0.067 Uiso 1 1 calc R U . . .
C3 C 0.9868(6) 0.14395(6) 0.49504(14) 0.0430(5) Uani 1 1 d . . . . .
H3A H 1.065261 0.172750 0.477840 0.056 Uiso 1 1 calc R U . . .
C4 C 0.9221(5) 0.13629(6) 0.59297(13) 0.0373(5) Uani 1 1 d . . . . .
C5 C 0.8143(6) 0.09223(6) 0.61300(14) 0.0450(5) Uani 1 1 d . . . . .
C6 C 0.7640(6) 0.05808(6) 0.54386(16) 0.0528(6) Uani 1 1 d . . . . .
H6 H 0.690142 0.028994 0.560637 0.069 Uiso 1 1 calc R U . . .
C7 C 0.9549(5) 0.17370(6) 0.66731(13) 0.0371(5) Uani 1 1 d . . . . .
C8 C 0.8265(5) 0.21691(6) 0.64092(14) 0.0394(5) Uani 1 1 d . . . . .
H8 H 0.718055 0.221835 0.576696 0.051 Uiso 1 1 calc R U . . .
C9 C 0.8556(5) 0.25311(6) 0.70804(13) 0.0402(5) Uani 1 1 d . . . . .
C10 C 1.0183(6) 0.24553(6) 0.80477(14) 0.0456(5) Uani 1 1 d . . . . .
C11 C 1.1506(6) 0.20251(7) 0.83149(15) 0.0477(5) Uani 1 1 d . . . . .
H11 H 1.261682 0.197488 0.895389 0.062 Uiso 1 1 calc R U . . .
C12 C 1.1183(6) 0.16738(6) 0.76419(14) 0.0440(5) Uani 1 1 d . . . . .
H12 H 1.207006 0.138639 0.783341 0.057 Uiso 1 1 calc R U . . .
C13 C 0.7158(6) 0.29879(7) 0.68007(16) 0.0497(6) Uani 1 1 d . . . . .
C14 C 0.3866(15) 0.42072(15) 0.6201(4) 0.0510(13) Uani 0.5 1 d D . P A 1
H14 H 0.494298 0.412799 0.682942 0.061 Uiso 0.5 1 calc R U P A 1
C15 C 0.2692(15) 0.46500(15) 0.6041(3) 0.0505(13) Uani 0.5 1 d D . P A 1
H15 H 0.290908 0.485842 0.656382 0.061 Uiso 0.5 1 calc R U P A 1
C16 C 0.120(2) 0.4787(3) 0.5115(6) 0.0303(17) Uani 0.5 1 d D . P A 1
C17 C 0.137(5) 0.4474(5) 0.4376(10) 0.033(3) Uani 0.5 1 d D U P A 1
H17 H 0.090703 0.456239 0.371379 0.040 Uiso 0.5 1 calc R U P A 1
C18 C 0.224(8) 0.4024(6) 0.4608(10) 0.048(2) Uani 0.5 1 d D U P A 1
H18 H 0.188457 0.380645 0.410486 0.057 Uiso 0.5 1 calc R U P A 1
H1 H 0.964(7) 0.3037(7) 0.8414(17) 0.091(9) Uiso 1 1 d D . . . .
H3 H 0.487(8) 0.3326(6) 0.578(2) 0.122(11) Uiso 1 1 d D . . . .
N1A N 0.242(3) 0.3841(4) 0.5499(9) 0.050(3) Uani 0.5 1 d D U P B 2
C14A C 0.1469(15) 0.41142(16) 0.6199(4) 0.0525(13) Uani 0.5 1 d D . P B 2
H14A H 0.159181 0.399866 0.684282 0.063 Uiso 0.5 1 calc R U P B 2
C15A C 0.0314(15) 0.45564(15) 0.6048(3) 0.0476(12) Uani 0.5 1 d D . P B 2
H15A H -0.026277 0.473370 0.657869 0.057 Uiso 0.5 1 calc R U P B 2
C16A C 0.002(2) 0.4734(3) 0.5099(7) 0.0323(18) Uani 0.5 1 d D . P B 2
C17A C 0.054(5) 0.4433(5) 0.4362(10) 0.032(3) Uani 0.5 1 d D U P B 2
H17A H -0.010432 0.451369 0.370173 0.039 Uiso 0.5 1 calc R U P B 2
C18A C 0.203(8) 0.4007(6) 0.4585(10) 0.044(2) Uani 0.5 1 d D U P B 2
H18A H 0.277431 0.383111 0.407372 0.053 Uiso 0.5 1 calc R U P B 2


_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
F1 C1 1.360(2) . ?
F2 C5 1.363(2) . ?
O1 C10 1.352(2) . ?
O1 H1 0.900(16) . ?
O2 C13 1.226(2) . ?
O3 C13 1.310(2) . ?
O3 H3 0.927(17) . ?
N1 C18 1.306(11) . ?
N1 C14 1.334(11) . ?
C1 C2 1.365(3) . ?
C1 C6 1.366(3) . ?
C2 C3 1.375(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.391(2) . ?
C3 H3A 0.9300 . ?
C4 C5 1.386(2) . ?
C4 C7 1.481(2) . ?
C5 C6 1.366(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.385(2) . ?
C7 C12 1.398(2) . ?
C8 C9 1.390(2) . ?
C8 H8 0.9300 . ?
C9 C10 1.401(3) . ?
C9 C13 1.469(3) . ?
C10 C11 1.386(3) . ?
C11 C12 1.368(3) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C14 C15 1.377(6) . ?
C14 H14 0.9300 . ?
C15 C16 1.375(8) . ?
C15 H15 0.9300 . ?
C16 C17 1.363(9) . ?
C17 C18 1.381(10) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
N1A C14A 1.318(11) . ?
N1A C18A 1.320(11) . ?
C14A C15A 1.371(6) . ?
C14A H14A 0.9300 . ?
C15A C16A 1.378(8) . ?
C15A H15A 0.9300 . ?
C16A C17A 1.361(9) . ?
C17A C18A 1.384(10) . ?
C17A H17A 0.9300 . ?
C18A H18A 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 O1 H1 103.2(16) . . ?
C13 O3 H3 109.0(18) . . ?
C18 N1 C14 116.1(10) . . ?
F1 C1 C2 118.89(19) . . ?
F1 C1 C6 118.37(18) . . ?
C2 C1 C6 122.74(19) . . ?
C1 C2 C3 117.95(19) . . ?
C1 C2 H2 121.0 . . ?
C3 C2 H2 121.0 . . ?
C2 C3 C4 122.90(17) . . ?
C2 C3 H3A 118.5 . . ?
C4 C3 H3A 118.5 . . ?
C5 C4 C3 114.95(17) . . ?
C5 C4 C7 123.85(17) . . ?
C3 C4 C7 121.16(16) . . ?
F2 C5 C6 116.73(17) . . ?
F2 C5 C4 118.78(17) . . ?
C6 C5 C4 124.47(19) . . ?
C1 C6 C5 116.97(18) . . ?
C1 C6 H6 121.5 . . ?
C5 C6 H6 121.5 . . ?
C8 C7 C12 117.89(17) . . ?
C8 C7 C4 119.79(17) . . ?
C12 C7 C4 122.31(16) . . ?
C7 C8 C9 121.65(18) . . ?
C7 C8 H8 119.2 . . ?
C9 C8 H8 119.2 . . ?
C8 C9 C10 119.00(17) . . ?
C8 C9 C13 121.49(17) . . ?
C10 C9 C13 119.50(17) . . ?
O1 C10 C11 117.67(19) . . ?
O1 C10 C9 122.62(17) . . ?
C11 C10 C9 119.71(17) . . ?
C12 C11 C10 120.23(18) . . ?
C12 C11 H11 119.9 . . ?
C10 C11 H11 119.9 . . ?
C11 C12 C7 121.50(18) . . ?
C11 C12 H12 119.2 . . ?
C7 C12 H12 119.2 . . ?
O2 C13 O3 121.90(19) . . ?
O2 C13 C9 122.6(2) . . ?
O3 C13 C9 115.47(17) . . ?
N1 C14 C15 122.8(6) . . ?
N1 C14 H14 118.6 . . ?
C15 C14 H14 118.6 . . ?
C16 C15 C14 120.6(6) . . ?
C16 C15 H15 119.7 . . ?
C14 C15 H15 119.7 . . ?
C17 C16 C15 115.2(9) . . ?
C16 C17 C18 120.0(11) . . ?
C16 C17 H17 120.0 . . ?
C18 C17 H17 120.0 . . ?
N1 C18 C17 123.7(13) . . ?
N1 C18 H18 118.1 . . ?
C17 C18 H18 118.1 . . ?
C14A N1A C18A 116.1(11) . . ?
N1A C14A C15A 124.8(7) . . ?
N1A C14A H14A 117.6 . . ?
C15A C14A H14A 117.6 . . ?
C14A C15A C16A 119.1(6) . . ?
C14A C15A H15A 120.5 . . ?
C16A C15A H15A 120.5 . . ?
C17A C16A C15A 115.8(9) . . ?
C16A C17A C18A 120.6(11) . . ?
C16A C17A H17A 119.7 . . ?
C18A C17A H17A 119.7 . . ?
N1A C18A C17A 122.3(13) . . ?
N1A C18A H18A 118.8 . . ?
C17A C18A H18A 118.8 . . ?

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
F1 C1 C2 C3 178.93(19) . . . . ?
C6 C1 C2 C3 -0.6(4) . . . . ?
C1 C2 C3 C4 -0.5(3) . . . . ?
C2 C3 C4 C5 1.5(3) . . . . ?
C2 C3 C4 C7 -176.2(2) . . . . ?
C3 C4 C5 F2 -179.55(18) . . . . ?
C7 C4 C5 F2 -1.9(3) . . . . ?
C3 C4 C5 C6 -1.4(3) . . . . ?
C7 C4 C5 C6 176.2(2) . . . . ?
F1 C1 C6 C5 -178.8(2) . . . . ?
C2 C1 C6 C5 0.7(4) . . . . ?
F2 C5 C6 C1 178.5(2) . . . . ?
C4 C5 C6 C1 0.3(4) . . . . ?
C5 C4 C7 C8 -136.0(2) . . . . ?
C3 C4 C7 C8 41.5(3) . . . . ?
C5 C4 C7 C12 45.2(3) . . . . ?
C3 C4 C7 C12 -137.3(2) . . . . ?
C12 C7 C8 C9 -0.3(3) . . . . ?
C4 C7 C8 C9 -179.24(18) . . . . ?
C7 C8 C9 C10 -0.1(3) . . . . ?
C7 C8 C9 C13 -179.39(19) . . . . ?
C8 C9 C10 O1 -179.86(19) . . . . ?
C13 C9 C10 O1 -0.6(3) . . . . ?
C8 C9 C10 C11 0.8(3) . . . . ?
C13 C9 C10 C11 -179.98(19) . . . . ?
O1 C10 C11 C12 179.70(19) . . . . ?
C9 C10 C11 C12 -0.9(3) . . . . ?
C10 C11 C12 C7 0.4(3) . . . . ?
C8 C7 C12 C11 0.2(3) . . . . ?
C4 C7 C12 C11 179.09(19) . . . . ?
C8 C9 C13 O2 -178.2(2) . . . . ?
C10 C9 C13 O2 2.6(3) . . . . ?
C8 C9 C13 O3 2.0(3) . . . . ?
C10 C9 C13 O3 -177.26(19) . . . . ?
C18 N1 C14 C15 4.9(19) . . . . ?
N1 C14 C15 C16 -2.4(10) . . . . ?
C14 C15 C16 C17 -7.2(12) . . . . ?
C15 C16 C17 C18 14(2) . . . . ?
C14 N1 C18 C17 2(3) . . . . ?
C16 C17 C18 N1 -12(4) . . . . ?
C18A N1A C14A C15A -4(2) . . . . ?
N1A C14A C15A C16A 1.5(11) . . . . ?
C14A C15A C16A C17A 7.1(11) . . . . ?
C15A C16A C17A C18A -14(2) . . . . ?
C14A N1A C18A C17A -3(3) . . . . ?
C16A C17A C18A N1A 12(4) . . . . ?

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
O1 H1 O2 0.900(16) 1.752(19) 2.588(2) 153(2) . yes
O3 H3 N1^a 0.927(17) 1.75(2) 2.673(11) 177(3) . yes
O3 H3 N1A^b 0.927(17) 1.79(2) 2.691(12) 165(3) . yes

_refine_diff_density_max         0.155
_refine_diff_density_min         -0.193
_refine_diff_density_rms         0.037

