# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1985339'
loop_
_audit_author_name
_audit_author_address
'Deborah Romito'
;Cardiff University
United Kingdom
;
_audit_update_record             
;
2020-02-20 deposited with the CCDC.	2022-04-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            1,7_N2PXX
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H8 N2 O2'
_chemical_formula_weight         284.26

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      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                   4.3819(9)
_cell_length_b                   13.469(3)
_cell_length_c                   10.1801(18)
_cell_angle_alpha                90
_cell_angle_beta                 97.073(19)
_cell_angle_gamma                90
_cell_volume                     596.3(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    634
_cell_measurement_theta_min      3.6240
_cell_measurement_theta_max      28.8590

_exptl_crystal_description       Needle
_exptl_crystal_colour            Yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.583
_exptl_crystal_F_000             292
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.221
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.072
_exptl_absorpt_coefficient_mu    0.106
_shelx_estimated_absorpt_T_min   0.977
_shelx_estimated_absorpt_T_max   0.992
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_correction_T_min  0.814
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            2815
_diffrn_reflns_av_unetI/netI     0.0575
_diffrn_reflns_av_R_equivalents  0.0352
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.025
_diffrn_reflns_theta_max         29.488
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.852
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.852
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.852
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             1409
_reflns_number_gt                702
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.1115P)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         1409
_refine_ls_number_parameters     100
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1359
_refine_ls_R_factor_gt           0.0684
_refine_ls_wR_factor_ref         0.2422
_refine_ls_wR_factor_gt          0.1879
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_restrained_S_all      1.010
_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 0.2696(4) 0.63134(11) 0.63406(17) 0.0285(6) Uani 1 1 d . . . . .
N1 N 0.0250(5) 0.54601(15) 0.7822(2) 0.0316(6) Uani 1 1 d . . . . .
C1 C 0.5399(5) 0.54711(15) 0.4760(2) 0.0213(6) Uani 1 1 d . . . . .
C2 C 0.2824(5) 0.45111(17) 0.6295(2) 0.0223(6) Uani 1 1 d . . . . .
C3 C 0.4462(6) 0.63329(17) 0.5299(2) 0.0239(6) Uani 1 1 d . . . . .
C4 C 0.1896(6) 0.54071(17) 0.6846(2) 0.0254(6) Uani 1 1 d . . . . .
C5 C 0.7033(5) 0.72829(18) 0.3758(2) 0.0281(7) Uani 1 1 d . . . . .
H5 H 0.7578 0.7909 0.3425 0.034 Uiso 1 1 calc R U . . .
C6 C 0.8034(6) 0.64008(17) 0.3183(2) 0.0251(6) Uani 1 1 d . . . . .
C7 C -0.0587(6) 0.45637(19) 0.8322(3) 0.0329(7) Uani 1 1 d . . . . .
H7 H -0.1796 0.4582 0.9035 0.040 Uiso 1 1 calc R U . . .
C8 C 0.5279(6) 0.72478(17) 0.4794(2) 0.0279(6) Uani 1 1 d . . . . .
H8 H 0.4626 0.7847 0.5166 0.033 Uiso 1 1 calc R U . . .
C9 C 0.0169(6) 0.36604(19) 0.7883(3) 0.0301(7) Uani 1 1 d . . . . .
H9 H -0.0494 0.3074 0.8282 0.036 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 C4 1.386(3) . ?
O1 C3 1.388(3) . ?
N1 C4 1.300(3) . ?
N1 C7 1.377(3) . ?
C1 C3 1.368(3) . ?
C1 C2 1.402(4) 3_666 ?
C1 C1 1.419(4) 3_666 ?
C2 C1 1.402(4) 3_666 ?
C2 C6 1.408(3) 3_666 ?
C2 C4 1.412(3) . ?
C3 C8 1.398(3) . ?
C5 C8 1.380(3) . ?
C5 C6 1.418(3) . ?
C5 H5 0.9500 . ?
C6 C2 1.408(3) 3_666 ?
C6 C9 1.419(4) 3_666 ?
C7 C9 1.351(3) . ?
C7 H7 0.9500 . ?
C8 H8 0.9500 . ?
C9 C6 1.419(4) 3_666 ?
C9 H9 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
C4 O1 C3 119.37(19) . . ?
C4 N1 C7 115.6(2) . . ?
C3 C1 C2 121.0(2) . 3_666 ?
C3 C1 C1 121.4(3) . 3_666 ?
C2 C1 C1 117.6(3) 3_666 3_666 ?
C1 C2 C6 120.2(2) 3_666 3_666 ?
C1 C2 C4 120.3(2) 3_666 . ?
C6 C2 C4 119.5(2) 3_666 . ?
C1 C3 O1 120.9(2) . . ?
C1 C3 C8 119.8(2) . . ?
O1 C3 C8 119.3(2) . . ?
N1 C4 O1 115.1(2) . . ?
N1 C4 C2 124.4(2) . . ?
O1 C4 C2 120.5(2) . . ?
C8 C5 C6 121.1(2) . . ?
C8 C5 H5 119.4 . . ?
C6 C5 H5 119.4 . . ?
C2 C6 C5 117.7(2) 3_666 . ?
C2 C6 C9 115.9(2) 3_666 3_666 ?
C5 C6 C9 126.4(2) . 3_666 ?
C9 C7 N1 125.4(2) . . ?
C9 C7 H7 117.3 . . ?
N1 C7 H7 117.3 . . ?
C5 C8 C3 120.2(2) . . ?
C5 C8 H8 119.9 . . ?
C3 C8 H8 119.9 . . ?
C7 C9 C6 119.1(2) . 3_666 ?
C7 C9 H9 120.4 . . ?
C6 C9 H9 120.4 3_666 . ?

_refine_diff_density_max         0.394
_refine_diff_density_min         -0.358
_refine_diff_density_rms         0.069


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: CHCl3'
####################################################################### 
# 
# 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_shelx_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1985342'
loop_
_audit_author_name
_audit_author_address
'Deborah Romito'
;Cardiff University
United Kingdom
;
_audit_update_record             
;
2020-02-20 deposited with the CCDC.	2022-04-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        ?
_chemical_name_common            3,9_N2PXX
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H12 N2 O4'
_chemical_formula_weight         320.30

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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'

_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                   7.5646(6)
_cell_length_b                   3.6755(3)
_cell_length_c                   23.933(2)
_cell_angle_alpha                90
_cell_angle_beta                 95.995(8)
_cell_angle_gamma                90
_cell_volume                     661.78(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    658
_cell_measurement_theta_min      6.6150
_cell_measurement_theta_max      71.6870

_exptl_crystal_description       Prism
_exptl_crystal_colour            Yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.607
_exptl_crystal_F_000             332
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.149
_exptl_crystal_size_mid          0.089
_exptl_crystal_size_min          0.059
_exptl_absorpt_coefficient_mu    0.963
_shelx_estimated_absorpt_T_min   0.870
_shelx_estimated_absorpt_T_max   0.945
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_correction_T_min  0.863
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.45b (Rigaku Oxford Diffraction, 2018)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.5082
_diffrn_reflns_number            2160
_diffrn_reflns_av_unetI/netI     0.0410
_diffrn_reflns_av_R_equivalents  0.0218
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         3.714
_diffrn_reflns_theta_max         74.052
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.965
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.965
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.965
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             1306
_reflns_number_gt                1027
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.1530P)²+0.1868P] 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         1306
_refine_ls_number_parameters     115
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0877
_refine_ls_R_factor_gt           0.0758
_refine_ls_wR_factor_ref         0.2465
_refine_ls_wR_factor_gt          0.2203
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_restrained_S_all      1.073
_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
C2 C 0.9359(3) 0.0370(6) 0.97678(9) 0.0234(6) Uani 1 1 d . . . . .
C3 C 0.9834(3) -0.0377(6) 0.92269(9) 0.0243(6) Uani 1 1 d . . . . .
C4 C 0.7711(3) 0.1776(6) 0.98405(9) 0.0251(6) Uani 1 1 d . . . . .
C5 C 1.1535(3) -0.1813(6) 0.91623(10) 0.0246(6) Uani 1 1 d . . . . .
C7 C 0.6480(3) 0.2461(6) 0.93729(11) 0.0291(6) Uani 1 1 d . . . . .
H7 H 0.534042 0.341851 0.942260 0.035 Uiso 1 1 calc R U . . .
C8 C 0.6932(3) 0.1737(7) 0.88393(10) 0.0301(6) Uani 1 1 d . . . . .
H8 H 0.609293 0.222167 0.852458 0.036 Uiso 1 1 calc R U . . .
C9 C 1.1973(3) -0.2480(7) 0.86304(10) 0.0298(6) Uani 1 1 d . . . . .
H9 H 1.311319 -0.338584 0.856881 0.036 Uiso 1 1 calc R U . . .
C10 C 0.8618(3) 0.0288(6) 0.87495(10) 0.0272(6) Uani 1 1 d . . . . .
C11 C 1.0664(3) -0.1770(7) 0.81759(10) 0.0321(6) Uani 1 1 d . . . . .
H11 H 1.096487 -0.229232 0.780869 0.038 Uiso 1 1 calc R U . . .
N1 N 0.9062(3) -0.0445(6) 0.82194(9) 0.0320(6) Uani 1 1 d . . . . .
O1 O 0.7251(2) 0.2532(5) 1.03776(7) 0.0280(5) Uani 1 1 d . . . . .
O2 O 0.3933(4) 0.3646(17) 0.76081(12) 0.1038(17) Uani 1 1 d D . . . .
H1 H 0.458(8) 0.179(16) 0.745(3) 0.125 Uiso 1 1 d D U . . .
H2 H 0.297(5) 0.386(19) 0.7321(18) 0.125 Uiso 1 1 d D U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C2 C4 1.377(3) . ?
C2 C3 1.406(3) . ?
C2 C2 1.423(5) 3_757 ?
C3 C10 1.411(3) . ?
C3 C5 1.414(3) . ?
C4 O1 1.394(3) . ?
C4 C7 1.402(3) . ?
C5 C9 1.371(3) . ?
C5 O1 1.384(3) 3_757 ?
C7 C8 1.382(3) . ?
C8 C10 1.419(3) . ?
C9 C11 1.417(4) . ?
C10 N1 1.373(3) . ?
C11 N1 1.321(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C4 C2 C3 120.7(2) . . ?
C4 C2 C2 121.7(3) . 3_757 ?
C3 C2 C2 117.5(2) . 3_757 ?
C2 C3 C10 120.3(2) . . ?
C2 C3 C5 119.8(2) . . ?
C10 C3 C5 120.0(2) . . ?
C2 C4 O1 120.5(2) . . ?
C2 C4 C7 120.1(2) . . ?
O1 C4 C7 119.42(19) . . ?
C9 C5 O1 120.0(2) . 3_757 ?
C9 C5 C3 118.7(2) . . ?
O1 C5 C3 121.3(2) 3_757 . ?
C8 C7 C4 119.7(2) . . ?
C7 C8 C10 121.7(2) . . ?
C5 C9 C11 117.6(2) . . ?
N1 C10 C3 120.8(2) . . ?
N1 C10 C8 121.6(2) . . ?
C3 C10 C8 117.5(2) . . ?
N1 C11 C9 125.5(2) . . ?
C11 N1 C10 117.4(2) . . ?
C5 O1 C4 119.12(17) 3_757 . ?

_refine_diff_density_max         0.455
_refine_diff_density_min         -0.420
_refine_diff_density_rms         0.091


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: CHCl3'
####################################################################### 
# 
# 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_shelx_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 2133474'
loop_
_audit_author_name
_audit_author_address
'Deborah Romito'
;University of Vienna
Austria
;
_audit_update_record             
;
2022-01-10 deposited with the CCDC.	2022-04-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        4,10-N,N-PXX:DITFB
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H8 F4 I2 N2 O2'
_chemical_formula_weight         686.12

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'
I I -0.4742 1.8119 '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                   4.1848(3)
_cell_length_b                   7.7399(5)
_cell_length_c                   16.2513(11)
_cell_angle_alpha                92.097(5)
_cell_angle_beta                 90.002(5)
_cell_angle_gamma                99.199(5)
_cell_volume                     519.25(6)
_cell_formula_units_Z            1
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    1410
_cell_measurement_theta_min      4.5130
_cell_measurement_theta_max      27.6660

_exptl_crystal_description       Prism
_exptl_crystal_colour            Orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.194
_exptl_crystal_F_000             324
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.390
_exptl_crystal_size_mid          0.122
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    3.091
_shelx_estimated_absorpt_T_min   0.379
_shelx_estimated_absorpt_T_max   0.790
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_correction_T_min  0.174
_exptl_absorpt_correction_T_max  0.752
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.5082
_diffrn_reflns_number            4071
_diffrn_reflns_av_unetI/netI     0.0698
_diffrn_reflns_av_R_equivalents  0.0338
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.730
_diffrn_reflns_theta_max         29.760
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.832
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.832
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.832
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             2460
_reflns_number_gt                2025
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0169P)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         2460
_refine_ls_number_parameters     154
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0546
_refine_ls_R_factor_gt           0.0407
_refine_ls_wR_factor_ref         0.0703
_refine_ls_wR_factor_gt          0.0630
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_restrained_S_all      1.035
_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
C1 C 0.0891(9) 0.7093(6) 0.8463(3) 0.0288(11) Uani 1 1 d . . . . .
H1 H 0.045144 0.813948 0.823018 0.035 Uiso 1 1 calc R U . . .
C2 C -0.0156(9) 0.6746(6) 0.9270(3) 0.0235(10) Uani 1 1 d . . . . .
C3 C 0.0479(9) 0.5238(6) 0.9593(3) 0.0238(10) Uani 1 1 d . . . . .
C4 C 0.2118(9) 0.4087(6) 0.9135(3) 0.0225(10) Uani 1 1 d . . . . .
C5 C 0.2776(9) 0.2520(6) 0.9475(3) 0.0273(10) Uani 1 1 d . . . . .
C6 C 0.4364(9) 0.1410(6) 0.9032(3) 0.0287(10) Uani 1 1 d . . . . .
H6 H 0.482999 0.036418 0.925979 0.034 Uiso 1 1 calc R U . . .
C7 C 0.5310(9) 0.1853(6) 0.8218(3) 0.0298(11) Uani 1 1 d . . . . .
H7 H 0.640111 0.107714 0.789938 0.036 Uiso 1 1 calc R U . . .
C8 C 0.4708(9) 0.3356(7) 0.7877(3) 0.0321(11) Uani 1 1 d . . . . .
H8 H 0.537601 0.360899 0.732938 0.038 Uiso 1 1 calc R U . . .
C9 C 0.3104(9) 0.4524(7) 0.8334(3) 0.0287(11) Uani 1 1 d . . . . .
C10 C 0.9530(11) 1.0793(7) 0.5740(3) 0.0362(12) Uani 1 1 d . . . . .
C11 C 0.8140(9) 0.9056(6) 0.5607(3) 0.0267(10) Uani 1 1 d . . . . .
C12 C 0.8633(10) 0.8294(7) 0.4856(3) 0.0350(12) Uani 1 1 d . . . . .
N1 N 0.2432(8) 0.6064(5) 0.8013(2) 0.0295(9) Uani 1 1 d . . . . .
O1 O -0.1794(6) 0.7895(4) 0.97128(19) 0.0297(7) Uani 1 1 d . . . . .
F1 F 0.9149(8) 1.1610(4) 0.64672(19) 0.0686(10) Uani 1 1 d . . . . .
F2 F 0.7330(8) 0.6629(4) 0.4681(2) 0.0731(11) Uani 1 1 d . . . . .
I1 I 0.55564(6) 0.76565(4) 0.65355(2) 0.03188(12) 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
C1 N1 1.306(6) . ?
C1 C2 1.405(6) . ?
C2 C3 1.361(6) . ?
C2 O1 1.388(5) . ?
C3 C4 1.402(6) . ?
C3 C3 1.427(8) 2_567 ?
C4 C9 1.403(6) . ?
C4 C5 1.417(6) . ?
C5 C6 1.354(6) . ?
C5 O1 1.416(5) 2_567 ?
C6 C7 1.419(6) . ?
C7 C8 1.365(6) . ?
C8 C9 1.402(6) . ?
C9 N1 1.387(6) . ?
C10 F1 1.341(6) . ?
C10 C12 1.380(6) 2_776 ?
C10 C11 1.386(7) . ?
C11 C12 1.366(6) . ?
C11 I1 2.089(4) . ?
C12 F2 1.337(6) . ?

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
N1 C1 C2 124.0(4) . . ?
C3 C2 O1 121.8(4) . . ?
C3 C2 C1 117.3(4) . . ?
O1 C2 C1 120.9(4) . . ?
C2 C3 C4 121.0(4) . . ?
C2 C3 C3 121.7(5) . 2_567 ?
C4 C3 C3 117.3(5) . 2_567 ?
C3 C4 C9 118.6(4) . . ?
C3 C4 C5 120.7(4) . . ?
C9 C4 C5 120.7(4) . . ?
C6 C5 O1 119.2(4) . 2_567 ?
C6 C5 C4 120.7(4) . . ?
O1 C5 C4 120.1(4) 2_567 . ?
C5 C6 C7 118.1(4) . . ?
C8 C7 C6 122.4(5) . . ?
C7 C8 C9 120.0(4) . . ?
N1 C9 C8 122.1(4) . . ?
N1 C9 C4 119.7(4) . . ?
C8 C9 C4 118.2(4) . . ?
F1 C10 C12 118.6(5) . 2_776 ?
F1 C10 C11 119.9(4) . . ?
C12 C10 C11 121.5(5) 2_776 . ?
C12 C11 C10 117.1(4) . . ?
C12 C11 I1 121.9(3) . . ?
C10 C11 I1 121.0(4) . . ?
F2 C12 C11 120.3(4) . . ?
F2 C12 C10 118.3(5) . 2_776 ?
C11 C12 C10 121.4(5) . 2_776 ?
C1 N1 C9 119.5(4) . . ?
C2 O1 C5 118.4(3) . 2_567 ?

_refine_diff_density_max         0.934
_refine_diff_density_min         -0.685
_refine_diff_density_rms         0.146

####################################################################### 
# 
# 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_shelx_CCDC3
_database_code_depnum_ccdc_archive 'CCDC 1985344'
loop_
_audit_author_name
_audit_author_address
'Deborah Romito'
;Cardiff University
United Kingdom
;
_audit_update_record             
;
2020-02-20 deposited with the CCDC.	2022-04-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            4,10_N2PXX
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H8 N2 O2'
_chemical_formula_weight         284.26

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'

_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                   11.589(3)
_cell_length_b                   3.7599(12)
_cell_length_c                   14.384(3)
_cell_angle_alpha                90
_cell_angle_beta                 112.54(3)
_cell_angle_gamma                90
_cell_volume                     578.9(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    851
_cell_measurement_theta_min      6.0960
_cell_measurement_theta_max      68.9570

_exptl_crystal_description       Plate
_exptl_crystal_colour            Orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.631
_exptl_crystal_F_000             292
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.469
_exptl_crystal_size_mid          0.044
_exptl_crystal_size_min          0.031
_exptl_absorpt_coefficient_mu    0.891
_shelx_estimated_absorpt_T_min   0.680
_shelx_estimated_absorpt_T_max   0.973
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_correction_T_min  0.629
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.5082
_diffrn_reflns_number            4883
_diffrn_reflns_av_unetI/netI     0.0535
_diffrn_reflns_av_R_equivalents  0.0748
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         4.195
_diffrn_reflns_theta_max         76.679
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.960
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.960
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.960
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             1171
_reflns_number_gt                678
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.1946P)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         1171
_refine_ls_number_parameters     100
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1251
_refine_ls_R_factor_gt           0.0899
_refine_ls_wR_factor_ref         0.2993
_refine_ls_wR_factor_gt          0.2405
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_restrained_S_all      1.011
_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
C1 C 0.1266(3) 0.5456(10) -0.0471(2) 0.0334(9) Uani 1 1 d . . . . .
C2 C 0.0812(3) 0.6958(10) 0.1255(2) 0.0338(9) Uani 1 1 d . . . . .
C3 C 0.2196(3) 0.7042(10) 0.0375(2) 0.0345(9) Uani 1 1 d . . . . .
C4 C -0.1470(3) 0.5332(10) 0.1354(2) 0.0377(9) Uani 1 1 d . . . . .
C5 C -0.0092(3) 0.5424(10) 0.0451(2) 0.0343(9) Uani 1 1 d . . . . .
C6 C 0.3348(3) 0.7828(10) 0.0359(2) 0.0381(9) Uani 1 1 d . . . . .
H6 H 0.398910 0.885375 0.092738 0.046 Uiso 1 1 calc R U . . .
C7 C 0.2655(3) 0.5524(10) -0.1361(2) 0.0399(9) Uani 1 1 d . . . . .
H7 H 0.283347 0.503794 -0.194011 0.048 Uiso 1 1 calc R U . . .
C8 C 0.0547(3) 0.7643(10) 0.2117(2) 0.0368(9) Uani 1 1 d . . . . .
H8 H 0.118041 0.869029 0.268590 0.044 Uiso 1 1 calc R U . . .
C9 C 0.3546(3) 0.7056(10) -0.0530(2) 0.0383(9) Uani 1 1 d . . . . .
H9 H 0.433372 0.762562 -0.055277 0.046 Uiso 1 1 calc R U . . .
N1 N -0.0541(3) 0.6895(9) 0.21714(19) 0.0413(9) Uani 1 1 d . . . . .
O1 O 0.1972(2) 0.7848(7) 0.12438(15) 0.0376(8) 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
C1 C4 1.410(4) 3_565 ?
C1 C5 1.410(5) 3_565 ?
C1 C3 1.412(5) . ?
C2 C5 1.356(5) . ?
C2 O1 1.390(4) . ?
C2 C8 1.411(4) . ?
C3 C6 1.376(5) . ?
C3 O1 1.404(4) . ?
C4 N1 1.384(5) . ?
C4 C7 1.415(5) 3_565 ?
C5 C5 1.429(5) 3_565 ?
C6 C9 1.413(4) . ?
C7 C9 1.372(5) . ?
C8 N1 1.324(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C4 C1 C5 117.7(3) 3_565 3_565 ?
C4 C1 C3 121.9(3) 3_565 . ?
C5 C1 C3 120.4(3) 3_565 . ?
C5 C2 O1 121.8(3) . . ?
C5 C2 C8 118.0(3) . . ?
O1 C2 C8 120.2(3) . . ?
C6 C3 O1 118.7(3) . . ?
C6 C3 C1 120.2(3) . . ?
O1 C3 C1 121.1(3) . . ?
N1 C4 C1 120.7(3) . 3_565 ?
N1 C4 C7 122.1(3) . 3_565 ?
C1 C4 C7 117.2(3) 3_565 3_565 ?
C2 C5 C1 121.2(3) . 3_565 ?
C2 C5 C5 122.2(4) . 3_565 ?
C1 C5 C5 116.5(4) 3_565 3_565 ?
C3 C6 C9 117.8(3) . . ?
C9 C7 C4 119.9(3) . 3_565 ?
N1 C8 C2 123.1(3) . . ?
C7 C9 C6 123.1(3) . . ?
C8 N1 C4 119.2(3) . . ?
C2 O1 C3 117.9(2) . . ?

_refine_diff_density_max         0.579
_refine_diff_density_min         -0.347
_refine_diff_density_rms         0.108


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: CHCl3'
####################################################################### 
# 
# 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_shelx_CCDC4
_database_code_depnum_ccdc_archive 'CCDC 2133475'
loop_
_audit_author_name
_audit_author_address
'Deborah Romito'
;University of Vienna
Austria
;
_audit_update_record             
;
2022-01-10 deposited with the CCDC.	2022-04-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        3,9-N,N-PXX:DITFB
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H8 F4 I2 N2 O2'
_chemical_formula_weight         686.12

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0028 0.0015 '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 0.0056 0.0031 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0101 0.0057 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4882 1.7230 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0164 0.0097 '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                   4.2046(2)
_cell_length_b                   6.7216(2)
_cell_length_c                   18.2394(5)
_cell_angle_alpha                94.632(3)
_cell_angle_beta                 93.684(3)
_cell_angle_gamma                99.922(3)
_cell_volume                     504.50(3)
_cell_formula_units_Z            1
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    7689
_cell_measurement_theta_min      1.089
_cell_measurement_theta_max      35.928

_exptl_crystal_description       prysm
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.258
_exptl_crystal_F_000             324
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.020
_exptl_crystal_size_mid          0.017
_exptl_crystal_size_min          0.005
_exptl_absorpt_coefficient_mu    2.888
_shelx_estimated_absorpt_T_min   0.944
_shelx_estimated_absorpt_T_max   0.986
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.6889
_diffrn_radiation_type           synchrotron
_diffrn_source                   synchrotron
_diffrn_measurement_device_type  synchrotron
_diffrn_measurement_method       dual-space
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7689
_diffrn_reflns_av_unetI/netI     0.1109
_diffrn_reflns_av_R_equivalents  0.0615
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         1.089
_diffrn_reflns_theta_max         35.929
_diffrn_reflns_theta_full        24.415
_diffrn_measured_fraction_theta_max 0.784
_diffrn_measured_fraction_theta_full 0.959
_diffrn_reflns_Laue_measured_fraction_max 0.784
_diffrn_reflns_Laue_measured_fraction_full 0.959
_diffrn_reflns_point_group_measured_fraction_max 0.784
_diffrn_reflns_point_group_measured_fraction_full 0.959
_reflns_number_total             4100
_reflns_number_gt                2795
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)] 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         4100
_refine_ls_number_parameters     154
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0775
_refine_ls_R_factor_gt           0.0514
_refine_ls_wR_factor_ref         0.1270
_refine_ls_wR_factor_gt          0.1171
_refine_ls_goodness_of_fit_ref   0.956
_refine_ls_restrained_S_all      0.956
_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
C1 C 0.6193(12) 0.3873(7) 0.2578(2) 0.0352(9) Uani 1 1 d . . . . .
H1 H 0.659614 0.348523 0.208498 0.042 Uiso 1 1 calc R U . . .
C2 C 0.7152(12) 0.2686(7) 0.3132(2) 0.0348(9) Uani 1 1 d . . . . .
H2 H 0.811963 0.153528 0.301453 0.042 Uiso 1 1 calc R U . . .
C3 C 0.6620(10) 0.3275(6) 0.3851(2) 0.0302(8) Uani 1 1 d . . . . .
C4 C 0.5098(10) 0.4960(6) 0.3985(2) 0.0281(8) Uani 1 1 d . . . . .
C5 C 0.4217(11) 0.6042(6) 0.3405(2) 0.0315(9) Uani 1 1 d . . . . .
C6 C 0.5502(10) 0.4416(6) 0.5280(2) 0.0285(8) Uani 1 1 d . . . . .
C7 C 0.6983(10) 0.2791(6) 0.5139(2) 0.0282(8) Uani 1 1 d . . . . .
C8 C 0.7928(11) 0.1701(6) 0.5709(2) 0.0317(9) Uani 1 1 d . . . . .
H8 H 0.898064 0.057875 0.560668 0.038 Uiso 1 1 calc R U . . .
C9 C 0.7316(10) 0.2270(6) 0.6429(2) 0.0308(9) Uani 1 1 d . . . . .
H9 H 0.793485 0.151687 0.681634 0.037 Uiso 1 1 calc R U . . .
C10 C 0.0038(11) 1.0789(7) 0.0711(2) 0.0310(8) Uani 1 1 d . . . . .
C11 C 0.1261(10) 0.9036(7) 0.0582(2) 0.0311(8) Uani 1 1 d . . . . .
C12 C 0.1226(11) 0.8234(6) -0.0147(2) 0.0301(8) Uani 1 1 d . . . . .
N1 N 0.4800(9) 0.5457(6) 0.26873(19) 0.0334(8) Uani 1 1 d . . . . .
O1 O 0.7610(8) 0.2196(5) 0.44159(17) 0.0340(7) Uani 1 1 d . . . . .
I1 I 0.29312(7) 0.75455(4) 0.14600(2) 0.03295(11) Uani 1 1 d . . . . .
F1 F 0.0019(7) 1.1639(4) 0.14104(13) 0.0394(6) Uani 1 1 d . . . . .
F2 F 0.2491(7) 0.6580(4) -0.03111(14) 0.0378(6) 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
C1 N1 1.308(6) . ?
C1 C2 1.418(6) . ?
C2 C3 1.382(6) . ?
C3 O1 1.390(5) . ?
C3 C4 1.406(6) . ?
C4 C5 1.397(6) . ?
C4 C6 1.424(6) 2_666 ?
C5 N1 1.386(5) . ?
C5 C9 1.420(6) 2_666 ?
C6 C7 1.362(6) . ?
C6 C6 1.424(8) 2_666 ?
C7 C8 1.396(6) . ?
C7 O1 1.402(5) . ?
C8 C9 1.389(6) . ?
C10 F1 1.357(5) . ?
C10 C11 1.374(6) . ?
C10 C12 1.389(6) 2_575 ?
C11 C12 1.392(6) . ?
C11 I1 2.102(4) . ?
C12 F2 1.334(5) . ?

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
N1 C1 C2 125.6(4) . . ?
C3 C2 C1 117.1(4) . . ?
C2 C3 O1 119.2(4) . . ?
C2 C3 C4 118.6(4) . . ?
O1 C3 C4 122.2(4) . . ?
C5 C4 C3 120.6(4) . . ?
C5 C4 C6 119.8(4) . 2_666 ?
C3 C4 C6 119.6(4) . 2_666 ?
N1 C5 C4 120.4(4) . . ?
N1 C5 C9 121.3(4) . 2_666 ?
C4 C5 C9 118.3(4) . 2_666 ?
C7 C6 C4 120.5(4) . 2_666 ?
C7 C6 C6 123.2(5) . 2_666 ?
C4 C6 C6 116.4(5) 2_666 2_666 ?
C6 C7 C8 120.9(4) . . ?
C6 C7 O1 120.4(3) . . ?
C8 C7 O1 118.8(4) . . ?
C9 C8 C7 119.4(4) . . ?
C8 C9 C5 121.1(3) . 2_666 ?
F1 C10 C11 120.2(4) . . ?
F1 C10 C12 117.1(4) . 2_575 ?
C11 C10 C12 122.7(4) . 2_575 ?
C10 C11 C12 117.7(4) . . ?
C10 C11 I1 121.1(3) . . ?
C12 C11 I1 121.2(3) . . ?
F2 C12 C10 119.7(4) . 2_575 ?
F2 C12 C11 120.7(4) . . ?
C10 C12 C11 119.5(4) 2_575 . ?
C1 N1 C5 117.7(4) . . ?
C3 O1 C7 118.3(3) . . ?

_refine_diff_density_max         1.721
_refine_diff_density_min         -1.428
_refine_diff_density_rms         0.176

####################################################################### 
# 
# 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_BCV403
_database_code_depnum_ccdc_archive 'CCDC 2151478'
loop_
_audit_author_name
_audit_author_address
'Nicola Demitri'
;Elettra Synchrotron XRD BLs
Italy
;
_audit_update_record             
;
2022-02-11 deposited with the CCDC.	2022-04-27 downloaded from the CCDC.
;

# start Validation Reply Form

_vrf_THETM01_BCV403              
;
PROBLEM: The value of sine(theta_max)/wavelength is less than 0.575 
         Calculated sin(theta_max)/wavelength = 0.5525
RESPONSE: Crystals diffracted poorly (best ones show reflections at a
          maximum resolution of 0.9-1.0 Ang) and were prone to radiation damage.
;

_vrf_RINTA01_BCV403              
;
PROBLEM:  The value of Rint is greater than 0.18 ............ Rint given 0.229
RESPONSE: Crystals diffracted poorly (best ones show reflections at a
          maximum resolution of 0.9-1.0 Ang) and were prone to radiation damage.
;

_vrf_PLAT020_BCV403              
;
PROBLEM:  The Value of Rint is Greater Than 0.12 ....................... 0.229
RESPONSE: Crystals diffracted poorly (best ones show reflections at a
          maximum resolution of 0.9-1.0 Ang) and were prone to radiation damage.
;

_vrf_PLAT026_BCV403              
;
PROBLEM:  Ratio Observed / Unique Reflections (too) Low .................. 38%
RESPONSE: Crystals diffracted poorly (best ones show reflections at a maximum
          resolution of 0.9-1.0 Ang). Low ratio is caused by weak data beyond 
          sin(theta)/lambda > 0.5.
;

_vrf_PLAT340_BCV403              
;
PROBLEM:  Low Bond Precision on  C-C Bonds ....................    0.01629 Ang
RESPONSE: Crystals diffracted poorly (best ones show reflections at a
          maximum resolution of 0.9-1.0 Ang) and were prone to radiation damage.
;

_vrf_PLAT430_BCV403              
; 
PROBLEM:  Short Inter D...A Contact O...N
RESPONSE: Disordered water molecules, with partial occupancies, have been
          successfully modeled into crystal channels. The corresponding
          hydrogen atoms cannot be located therefore hydrogen bonds cannot be
          properly determined.
;

_vrf_PLAT043_BCV403              
; 
PROBLEM:  Calculated and Reported Mol. Weight Differ by ............. 157.28
RESPONSE: Several disordered water molecules, with partial occupancies, have
          been successfully modeled into crystal channels. The corresponding
          hydrogen atoms cannot be located but they have been included
          into molecular formulas.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C27 H15 N3 O3, 4.88(H2 O)'
_chemical_formula_sum            'C27 H24.75 N3 O7.88'
_chemical_formula_weight         517.25

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0030 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0059 0.0032 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0105 0.0059 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_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+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   12.826(3)
_cell_length_b                   28.416(6)
_cell_length_c                   27.470(5)
_cell_angle_alpha                90
_cell_angle_beta                 101.61(3)
_cell_angle_gamma                90
_cell_volume                     9807(4)
_cell_formula_units_Z            16
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    181
_cell_measurement_theta_min      1.412
_cell_measurement_theta_max      22.751

_exptl_crystal_description       'Thin plates'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.401
_exptl_crystal_F_000             4332
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.020
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    0.100
_shelx_estimated_absorpt_T_min   0.990
_shelx_estimated_absorpt_T_max   0.998
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.700

_diffrn_radiation_type           Synchrotron
_diffrn_source                   'Elettra Synchrotron - XRD1 BL'
_diffrn_measurement_device_type  
;
'Huber 4-circles Kappa Goniometer, Pilatus 2M detector'
;
_diffrn_measurement_method       'Rotating crystal'

_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            24718
_diffrn_reflns_av_unetI/netI     0.1996
_diffrn_reflns_av_R_equivalents  0.2292
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         1.412
_diffrn_reflns_theta_max         22.751
_diffrn_reflns_theta_full        22.751
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measured_fraction_theta_full 0.978
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_Laue_measured_fraction_full 0.978
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_point_group_measured_fraction_full 0.978
_reflns_number_total             6786
_reflns_number_gt                2549
_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.
;

_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_decay_%        0

_computing_data_collection       'Elettra XRD1 Data Collection SW'
_computing_cell_refinement       'XDS (Kabsch, 2010)'
_computing_data_reduction        'XDS (Kabsch, 2010)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015)'
_computing_molecular_graphics    'Ortep3 for Windows - Coot'
_computing_publication_material  'enCIFer - publCIF'

_refine_special_details          
;
Hydrogen atoms were included at calculated positions with isotropic 
Ufactors=1.2Ueq (Ufactors=1.5Ueq for hydroxyl groups). Anisotropic 
thermal motion modeling has been applied to all atoms with full occupancies.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1586P)²+27.6285P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.0021(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         6786
_refine_ls_number_parameters     683
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2453
_refine_ls_R_factor_gt           0.1006
_refine_ls_wR_factor_ref         0.3480
_refine_ls_wR_factor_gt          0.2516
_refine_ls_goodness_of_fit_ref   0.992
_refine_ls_restrained_S_all      0.992
_refine_ls_shift/su_max          0.003
_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
O_11 O 0.1805(16) 0.7302(8) 0.7630(9) 0.121(7) Uiso 0.5 1 d . . P A 1
O_12 O 0.538(2) 0.2509(11) 0.2836(11) 0.181(11) Uiso 0.5 1 d . . P B 1
OA_13 O 0.3745(18) 0.3074(7) 0.3151(7) 0.083(9) Uiso 0.51(4) 1 d . . P C 1
OB_13 O 0.430(2) 0.2958(8) 0.3001(8) 0.097(10) Uiso 0.49(4) 1 d . . P C 2
O_14 O 0.0356(17) 0.5277(9) 0.2429(10) 0.052(7) Uiso 0.25 1 d . . P D 1
O_15 O -0.180(2) 0.7537(11) 0.5580(12) 0.181(11) Uiso 0.5 1 d . . P E 1
OA_16 O 0.098(2) 0.4634(17) 0.3341(10) 0.110(9) Uiso 0.58(7) 1 d . . P F 1
OB_16 O 0.0803(17) 0.4841(14) 0.3247(9) 0.059(12) Uiso 0.42(7) 1 d . . P F 2
OA_17 O 0.6552(14) 0.6684(4) 0.4846(9) 0.084(7) Uiso 0.73(5) 1 d . . P G 1
OB_17 O 0.689(4) 0.6667(11) 0.511(2) 0.078(17) Uiso 0.27(5) 1 d . . P G 2
OA_18 O -0.063(2) 0.6278(8) 0.6983(9) 0.104(11) Uiso 0.49(4) 1 d . . P H 1
OB_18 O -0.139(3) 0.6180(11) 0.6728(13) 0.167(16) Uiso 0.51(4) 1 d . . P H 2
O_19 O -0.245(2) 0.6811(12) 0.6789(13) 0.189(12) Uiso 0.5 1 d . . P I 1
OA_20 O -0.1165(13) 0.7745(6) 0.6078(7) 0.088(8) Uiso 0.51(3) 1 d . . P E 1
OB_20 O -0.1067(19) 0.7698(9) 0.6608(11) 0.145(12) Uiso 0.49(3) 1 d . . P E 2
OA_21 O -0.2534(17) 0.6937(9) 0.5807(13) 0.171(11) Uiso 0.70(4) 1 d . . P J 1
OB_21 O -0.247(2) 0.6806(12) 0.6153(17) 0.091(18) Uiso 0.30(4) 1 d . . P J 2
OA_22 O 0.0533(17) 0.7161(7) 0.6627(6) 0.096(8) Uiso 0.59(3) 1 d . . P K 1
OB_22 O 0.111(2) 0.7386(9) 0.6710(8) 0.083(11) Uiso 0.41(3) 1 d . . P K 2
O_23 O -0.013(4) 0.6704(16) 0.7252(16) 0.265(19) Uiso 0.5 1 d . . P H 1
N1_1 N 0.5345(5) 0.5460(3) 0.4455(3) 0.0386(19) Uani 1 1 d . . . . .
C2_1 C 0.4583(7) 0.5799(3) 0.4467(3) 0.044(2) Uani 1 1 d . . . . .
H2A_1 H 0.479641 0.611650 0.453077 0.053 Uiso 1 1 calc R U . . .
C3_1 C 0.3525(6) 0.5687(3) 0.4388(4) 0.042(2) Uani 1 1 d . . . . .
C4_1 C 0.3149(7) 0.5224(3) 0.4285(4) 0.045(3) Uani 1 1 d . . . . .
C5_1 C 0.3966(6) 0.4869(3) 0.4275(3) 0.038(2) Uani 1 1 d . . . . .
C6_1 C 0.5047(7) 0.4996(3) 0.4372(3) 0.041(2) Uani 1 1 d . . . . .
C7_1 C 0.5827(7) 0.4651(4) 0.4370(3) 0.042(2) Uani 1 1 d . . . . .
H7_1 H 0.655383 0.474106 0.441798 0.050 Uiso 1 1 calc R U . . .
C8_1 C 0.5561(7) 0.4194(3) 0.4301(3) 0.041(2) Uani 1 1 d . . . . .
H8_1 H 0.609752 0.396299 0.430443 0.050 Uiso 1 1 calc R U . . .
C9_1 C 0.4481(7) 0.4060(4) 0.4223(4) 0.049(3) Uani 1 1 d . . . . .
H9_1 H 0.429492 0.373719 0.418163 0.058 Uiso 1 1 calc R U . . .
C10_1 C 0.3714(7) 0.4384(3) 0.4206(4) 0.044(2) Uani 1 1 d . . . . .
H10_1 H 0.299105 0.428704 0.414684 0.053 Uiso 1 1 calc R U . . .
C11_1 C 0.1334(7) 0.6522(3) 0.4296(4) 0.043(2) Uani 1 1 d . . . . .
C12_1 C 0.2013(7) 0.6196(3) 0.4157(4) 0.043(2) Uani 1 1 d . . . . .
C13_1 C 0.1811(7) 0.6040(4) 0.3662(4) 0.057(3) Uani 1 1 d . . . . .
H13_1 H 0.231568 0.582976 0.357036 0.069 Uiso 1 1 calc R U . . .
N14_1 N 0.0985(6) 0.6157(3) 0.3309(3) 0.060(2) Uani 1 1 d . . . . .
C15_1 C 0.0229(7) 0.6431(4) 0.3462(4) 0.054(3) Uani 1 1 d . . . . .
C16_1 C 0.0369(7) 0.6603(3) 0.3949(4) 0.046(3) Uani 1 1 d . . . . .
C17_1 C -0.0491(7) 0.6841(4) 0.4093(5) 0.054(3) Uani 1 1 d . . . . .
C18_1 C -0.1370(8) 0.6953(3) 0.3749(5) 0.058(3) Uani 1 1 d . . . . .
H18_1 H -0.192997 0.712257 0.384883 0.070 Uiso 1 1 calc R U . . .
C19_1 C -0.1470(8) 0.6827(4) 0.3253(5) 0.064(3) Uani 1 1 d . . . . .
H19_1 H -0.207288 0.692695 0.301554 0.077 Uiso 1 1 calc R U . . .
C20_1 C -0.0702(7) 0.6559(4) 0.3107(5) 0.065(3) Uani 1 1 d . . . . .
H20_1 H -0.078786 0.645766 0.277131 0.077 Uiso 1 1 calc R U . . .
C21_1 C 0.1439(7) 0.6764(3) 0.4780(4) 0.043(2) Uani 1 1 d . . . . .
C22_1 C 0.0502(8) 0.6917(3) 0.4903(5) 0.054(3) Uani 1 1 d . . . . .
C23_1 C 0.0481(10) 0.7073(4) 0.5388(5) 0.059(3) Uani 1 1 d . . . . .
H23_1 H -0.018683 0.714890 0.546773 0.071 Uiso 1 1 calc R U . . .
N24_1 N 0.1331(9) 0.7117(3) 0.5731(4) 0.065(3) Uani 1 1 d . . . . .
C25_1 C 0.2310(9) 0.7044(4) 0.5605(4) 0.053(3) Uani 1 1 d . . . . .
C26_1 C 0.2393(8) 0.6882(3) 0.5129(4) 0.048(3) Uani 1 1 d . . . . .
C27_1 C 0.3400(8) 0.6886(3) 0.4997(4) 0.051(3) Uani 1 1 d . . . . .
H27_1 H 0.346093 0.681110 0.466697 0.061 Uiso 1 1 calc R U . . .
C28_1 C 0.4283(9) 0.6997(4) 0.5341(4) 0.058(3) Uani 1 1 d . . . . .
H28_1 H 0.496212 0.699258 0.525271 0.070 Uiso 1 1 calc R U . . .
C29_1 C 0.4192(10) 0.7118(4) 0.5831(5) 0.065(3) Uani 1 1 d . . . . .
H29_1 H 0.481492 0.718118 0.607465 0.078 Uiso 1 1 calc R U . . .
C30_1 C 0.3218(10) 0.7145(4) 0.5957(4) 0.062(3) Uani 1 1 d . . . . .
H30_1 H 0.316235 0.723256 0.628424 0.074 Uiso 1 1 calc R U . . .
O1_1 O 0.2864(4) 0.6040(2) 0.4504(2) 0.0478(17) Uani 1 1 d . . . . .
O2_1 O 0.2180(5) 0.5107(2) 0.4212(3) 0.0552(19) Uani 1 1 d . . . . .
H2_1 H 0.180607 0.534665 0.423139 0.083 Uiso 1 1 calc R U . . .
O3_1 O -0.0468(5) 0.6929(2) 0.4590(3) 0.0559(19) Uani 1 1 d . . . . .
N1_2 N 1.0300(5) 0.5403(3) 0.4422(3) 0.0397(19) Uani 1 1 d . . . . .
C2_2 C 0.9404(7) 0.5315(3) 0.4079(4) 0.039(2) Uani 1 1 d . . . . .
H2A_2 H 0.945790 0.517259 0.377188 0.047 Uiso 1 1 calc R U . . .
C3_2 C 0.8430(7) 0.5427(3) 0.4166(3) 0.038(2) Uani 1 1 d . . . . .
C4_2 C 0.8269(6) 0.5648(3) 0.4605(3) 0.038(2) Uani 1 1 d . . . . .
C5_2 C 0.9255(6) 0.5737(3) 0.4971(4) 0.038(2) Uani 1 1 d . . . . .
C6_2 C 1.0251(7) 0.5609(3) 0.4869(4) 0.036(2) Uani 1 1 d . . . . .
C7_2 C 1.1187(7) 0.5678(3) 0.5220(4) 0.041(2) Uani 1 1 d . . . . .
H7_2 H 1.185397 0.559204 0.514545 0.049 Uiso 1 1 calc R U . . .
C8_2 C 1.1141(7) 0.5871(3) 0.5670(4) 0.045(3) Uani 1 1 d . . . . .
H8_2 H 1.177948 0.591845 0.590871 0.054 Uiso 1 1 calc R U . . .
C9_2 C 1.0157(7) 0.5999(4) 0.5786(4) 0.054(3) Uani 1 1 d . . . . .
H9_2 H 1.013241 0.612940 0.610250 0.064 Uiso 1 1 calc R U . . .
C10_2 C 0.9243(7) 0.5935(3) 0.5443(4) 0.046(3) Uani 1 1 d . . . . .
H10_2 H 0.858321 0.602618 0.552076 0.055 Uiso 1 1 calc R U . . .
C11_2 C 0.5862(7) 0.5346(4) 0.3307(3) 0.048(3) Uani 1 1 d . . . . .
C12_2 C 0.6766(7) 0.5551(4) 0.3577(4) 0.044(2) Uani 1 1 d . . . . .
C13_2 C 0.6844(7) 0.6041(4) 0.3611(4) 0.052(3) Uani 1 1 d . . . . .
H13_2 H 0.749693 0.616696 0.378932 0.063 Uiso 1 1 calc R U . . .
N14_2 N 0.6117(7) 0.6338(3) 0.3424(3) 0.060(3) Uani 1 1 d . . . . .
C15_2 C 0.5169(8) 0.6162(5) 0.3191(4) 0.060(3) Uani 1 1 d . . . . .
C16_2 C 0.5014(7) 0.5672(5) 0.3143(4) 0.059(3) Uani 1 1 d . . . . .
C17_2 C 0.3960(10) 0.5526(5) 0.2961(4) 0.070(4) Uani 1 1 d . . . . .
C18_2 C 0.3128(8) 0.5798(7) 0.2774(4) 0.078(5) Uani 1 1 d . . . . .
H18_2 H 0.244780 0.567252 0.263234 0.094 Uiso 1 1 calc R U . . .
C19_2 C 0.3333(11) 0.6285(7) 0.2803(5) 0.097(5) Uani 1 1 d . . . . .
H19_2 H 0.276505 0.649480 0.267853 0.116 Uiso 1 1 calc R U . . .
C20_2 C 0.4302(9) 0.6472(5) 0.3001(4) 0.079(4) Uani 1 1 d . . . . .
H20_2 H 0.440252 0.680296 0.301258 0.094 Uiso 1 1 calc R U . . .
C21_2 C 0.5636(9) 0.4861(4) 0.3191(4) 0.060(3) Uani 1 1 d . . . . .
C22_2 C 0.4556(11) 0.4721(5) 0.3079(4) 0.071(4) Uani 1 1 d . . . . .
C23_2 C 0.4310(16) 0.4251(8) 0.3048(5) 0.112(7) Uani 1 1 d . . . . .
H23_2 H 0.357528 0.417234 0.299319 0.135 Uiso 1 1 calc R U . . .
N24_2 N 0.4969(13) 0.3903(5) 0.3087(4) 0.094(5) Uani 1 1 d . . . . .
C25_2 C 0.6027(16) 0.4024(5) 0.3117(5) 0.093(5) Uani 1 1 d . . . . .
C26_2 C 0.6396(10) 0.4494(4) 0.3140(4) 0.062(3) Uani 1 1 d . . . . .
C27_2 C 0.7472(9) 0.4578(4) 0.3086(4) 0.060(3) Uani 1 1 d . . . . .
H27_2 H 0.772472 0.489290 0.310272 0.072 Uiso 1 1 calc R U . . .
C28_2 C 0.8143(11) 0.4228(5) 0.3011(4) 0.076(4) Uani 1 1 d . . . . .
H28_2 H 0.883494 0.429726 0.295643 0.091 Uiso 1 1 calc R U . . .
C29_2 C 0.7785(18) 0.3761(6) 0.3018(5) 0.105(6) Uani 1 1 d . . . . .
H29_2 H 0.824920 0.350731 0.298548 0.126 Uiso 1 1 calc R U . . .
C30_2 C 0.6729(18) 0.3670(6) 0.3074(5) 0.106(6) Uani 1 1 d . . . . .
H30_2 H 0.649922 0.335257 0.308229 0.127 Uiso 1 1 calc R U . . .
O1_2 O 0.7562(4) 0.5250(2) 0.3825(2) 0.0431(16) Uani 1 1 d . . . . .
O2_2 O 0.7394(5) 0.5762(2) 0.4695(2) 0.0496(18) Uani 1 1 d . . . . .
H2_2 H 0.690912 0.568996 0.445255 0.074 Uiso 1 1 calc R U . . .
O3_2 O 0.3752(6) 0.5046(4) 0.2992(3) 0.083(3) 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
OA_13 O_19 1.73(4) 5_566 ?
O_14 O_14 1.06(4) 2 ?
O_15 OA_20 1.56(3) . ?
OA_18 O_23 1.50(5) . ?
O_23 O_23 1.34(8) 2_556 ?
N1_1 C2_1 1.375(11) . ?
N1_1 C6_1 1.379(12) . ?
C2_1 C3_1 1.368(12) . ?
C2_1 H2A_1 0.9500 . ?
C3_1 O1_1 1.390(10) . ?
C3_1 C4_1 1.410(13) . ?
C4_1 O2_1 1.263(10) . ?
C4_1 C5_1 1.459(12) . ?
C5_1 C6_1 1.406(12) . ?
C5_1 C10_1 1.420(13) . ?
C6_1 C7_1 1.402(12) . ?
C7_1 C8_1 1.347(13) . ?
C7_1 H7_1 0.9500 . ?
C8_1 C9_1 1.410(12) . ?
C8_1 H8_1 0.9500 . ?
C9_1 C10_1 1.340(12) . ?
C9_1 H9_1 0.9500 . ?
C10_1 H10_1 0.9500 . ?
C11_1 C12_1 1.377(13) . ?
C11_1 C16_1 1.421(13) . ?
C11_1 C21_1 1.478(14) . ?
C12_1 O1_1 1.371(10) . ?
C12_1 C13_1 1.406(14) . ?
C13_1 N14_1 1.326(12) . ?
C13_1 H13_1 0.9500 . ?
N14_1 C15_1 1.374(12) . ?
C15_1 C16_1 1.402(15) . ?
C15_1 C20_1 1.428(14) . ?
C16_1 C17_1 1.416(13) . ?
C17_1 C18_1 1.356(14) . ?
C17_1 O3_1 1.380(13) . ?
C18_1 C19_1 1.388(16) . ?
C18_1 H18_1 0.9500 . ?
C19_1 C20_1 1.369(15) . ?
C19_1 H19_1 0.9500 . ?
C20_1 H20_1 0.9500 . ?
C21_1 C22_1 1.383(13) . ?
C21_1 C26_1 1.433(14) . ?
C22_1 O3_1 1.363(12) . ?
C22_1 C23_1 1.410(16) . ?
C23_1 N24_1 1.295(14) . ?
C23_1 H23_1 0.9500 . ?
N24_1 C25_1 1.383(13) . ?
C25_1 C30_1 1.386(14) . ?
C25_1 C26_1 1.411(15) . ?
C26_1 C27_1 1.410(14) . ?
C27_1 C28_1 1.357(14) . ?
C27_1 H27_1 0.9500 . ?
C28_1 C29_1 1.419(16) . ?
C28_1 H28_1 0.9500 . ?
C29_1 C30_1 1.363(15) . ?
C29_1 H29_1 0.9500 . ?
C30_1 H30_1 0.9500 . ?
O2_1 H2_1 0.8400 . ?
N1_2 C2_2 1.355(11) . ?
N1_2 C6_2 1.375(12) . ?
C2_2 C3_2 1.356(12) . ?
C2_2 H2A_2 0.9500 . ?
C3_2 O1_2 1.398(10) . ?
C3_2 C4_2 1.412(13) . ?
C4_2 O2_2 1.239(10) . ?
C4_2 C5_2 1.470(12) . ?
C5_2 C10_2 1.416(13) . ?
C5_2 C6_2 1.409(12) . ?
C6_2 C7_2 1.394(12) . ?
C7_2 C8_2 1.366(13) . ?
C7_2 H7_2 0.9500 . ?
C8_2 C9_2 1.410(13) . ?
C8_2 H8_2 0.9500 . ?
C9_2 C10_2 1.362(13) . ?
C9_2 H9_2 0.9500 . ?
C10_2 H10_2 0.9500 . ?
C11_2 C12_2 1.373(12) . ?
C11_2 C21_2 1.432(15) . ?
C11_2 C16_2 1.431(14) . ?
C12_2 O1_2 1.399(10) . ?
C12_2 C13_2 1.399(14) . ?
C13_2 N14_2 1.285(12) . ?
C13_2 H13_2 0.9500 . ?
N14_2 C15_2 1.351(13) . ?
C15_2 C16_2 1.410(16) . ?
C15_2 C20_2 1.431(15) . ?
C16_2 C17_2 1.406(15) . ?
C17_2 C18_2 1.335(17) . ?
C17_2 O3_2 1.396(15) . ?
C18_2 C19_2 1.41(2) . ?
C18_2 H18_2 0.9500 . ?
C19_2 C20_2 1.359(19) . ?
C19_2 H19_2 0.9500 . ?
C20_2 H20_2 0.9500 . ?
C21_2 C22_2 1.414(15) . ?
C21_2 C26_2 1.452(16) . ?
C22_2 C23_2 1.37(2) . ?
C22_2 O3_2 1.368(15) . ?
C23_2 N24_2 1.29(2) . ?
C23_2 H23_2 0.9500 . ?
N24_2 C25_2 1.39(2) . ?
C25_2 C30_2 1.37(2) . ?
C25_2 C26_2 1.415(17) . ?
C26_2 C27_2 1.437(16) . ?
C27_2 C28_2 1.357(15) . ?
C27_2 H27_2 0.9500 . ?
C28_2 C29_2 1.41(2) . ?
C28_2 H28_2 0.9500 . ?
C29_2 C30_2 1.42(2) . ?
C29_2 H29_2 0.9500 . ?
C30_2 H30_2 0.9500 . ?
O2_2 H2_2 0.8400 . ?

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
O_23 O_23 OA_18 120(3) 2_556 . ?
C2_1 N1_1 C6_1 119.8(7) . . ?
C3_1 C2_1 N1_1 121.4(9) . . ?
C3_1 C2_1 H2A_1 119.3 . . ?
N1_1 C2_1 H2A_1 119.3 . . ?
C2_1 C3_1 O1_1 115.4(8) . . ?
C2_1 C3_1 C4_1 122.4(8) . . ?
O1_1 C3_1 C4_1 121.2(7) . . ?
O2_1 C4_1 C3_1 124.3(8) . . ?
O2_1 C4_1 C5_1 120.1(9) . . ?
C3_1 C4_1 C5_1 115.6(8) . . ?
C6_1 C5_1 C10_1 117.6(8) . . ?
C6_1 C5_1 C4_1 120.2(9) . . ?
C10_1 C5_1 C4_1 122.0(8) . . ?
N1_1 C6_1 C7_1 119.7(8) . . ?
N1_1 C6_1 C5_1 120.5(8) . . ?
C7_1 C6_1 C5_1 119.8(9) . . ?
C8_1 C7_1 C6_1 121.0(9) . . ?
C8_1 C7_1 H7_1 119.5 . . ?
C6_1 C7_1 H7_1 119.5 . . ?
C7_1 C8_1 C9_1 119.6(8) . . ?
C7_1 C8_1 H8_1 120.2 . . ?
C9_1 C8_1 H8_1 120.2 . . ?
C10_1 C9_1 C8_1 120.8(10) . . ?
C10_1 C9_1 H9_1 119.6 . . ?
C8_1 C9_1 H9_1 119.6 . . ?
C9_1 C10_1 C5_1 121.1(9) . . ?
C9_1 C10_1 H10_1 119.5 . . ?
C5_1 C10_1 H10_1 119.5 . . ?
C12_1 C11_1 C16_1 115.9(9) . . ?
C12_1 C11_1 C21_1 127.9(9) . . ?
C16_1 C11_1 C21_1 115.9(8) . . ?
O1_1 C12_1 C11_1 119.0(9) . . ?
O1_1 C12_1 C13_1 122.4(8) . . ?
C11_1 C12_1 C13_1 118.6(8) . . ?
N14_1 C13_1 C12_1 126.3(9) . . ?
N14_1 C13_1 H13_1 116.9 . . ?
C12_1 C13_1 H13_1 116.9 . . ?
C13_1 N14_1 C15_1 115.5(9) . . ?
N14_1 C15_1 C16_1 121.7(9) . . ?
N14_1 C15_1 C20_1 118.7(10) . . ?
C16_1 C15_1 C20_1 119.5(10) . . ?
C15_1 C16_1 C11_1 120.7(9) . . ?
C15_1 C16_1 C17_1 118.4(9) . . ?
C11_1 C16_1 C17_1 120.8(10) . . ?
C18_1 C17_1 O3_1 119.8(10) . . ?
C18_1 C17_1 C16_1 120.1(12) . . ?
O3_1 C17_1 C16_1 119.9(9) . . ?
C17_1 C18_1 C19_1 121.6(10) . . ?
C17_1 C18_1 H18_1 119.2 . . ?
C19_1 C18_1 H18_1 119.2 . . ?
C20_1 C19_1 C18_1 120.2(10) . . ?
C20_1 C19_1 H19_1 119.9 . . ?
C18_1 C19_1 H19_1 119.9 . . ?
C19_1 C20_1 C15_1 119.5(11) . . ?
C19_1 C20_1 H20_1 120.3 . . ?
C15_1 C20_1 H20_1 120.3 . . ?
C22_1 C21_1 C26_1 115.4(10) . . ?
C22_1 C21_1 C11_1 116.1(9) . . ?
C26_1 C21_1 C11_1 128.4(8) . . ?
O3_1 C22_1 C21_1 125.5(11) . . ?
O3_1 C22_1 C23_1 113.6(9) . . ?
C21_1 C22_1 C23_1 120.9(10) . . ?
N24_1 C23_1 C22_1 122.9(10) . . ?
N24_1 C23_1 H23_1 118.5 . . ?
C22_1 C23_1 H23_1 118.5 . . ?
C23_1 N24_1 C25_1 118.5(10) . . ?
N24_1 C25_1 C30_1 118.2(11) . . ?
N24_1 C25_1 C26_1 121.5(10) . . ?
C30_1 C25_1 C26_1 120.3(10) . . ?
C27_1 C26_1 C25_1 118.6(10) . . ?
C27_1 C26_1 C21_1 122.2(10) . . ?
C25_1 C26_1 C21_1 118.9(9) . . ?
C28_1 C27_1 C26_1 120.2(11) . . ?
C28_1 C27_1 H27_1 119.9 . . ?
C26_1 C27_1 H27_1 119.9 . . ?
C27_1 C28_1 C29_1 120.0(11) . . ?
C27_1 C28_1 H28_1 120.0 . . ?
C29_1 C28_1 H28_1 120.0 . . ?
C30_1 C29_1 C28_1 120.6(11) . . ?
C30_1 C29_1 H29_1 119.7 . . ?
C28_1 C29_1 H29_1 119.7 . . ?
C29_1 C30_1 C25_1 119.8(12) . . ?
C29_1 C30_1 H30_1 120.1 . . ?
C25_1 C30_1 H30_1 120.1 . . ?
C12_1 O1_1 C3_1 120.8(8) . . ?
C4_1 O2_1 H2_1 109.5 . . ?
C22_1 O3_1 C17_1 117.0(8) . . ?
C2_2 N1_2 C6_2 121.0(7) . . ?
N1_2 C2_2 C3_2 121.1(9) . . ?
N1_2 C2_2 H2A_2 119.4 . . ?
C3_2 C2_2 H2A_2 119.4 . . ?
C2_2 C3_2 O1_2 115.8(8) . . ?
C2_2 C3_2 C4_2 123.7(8) . . ?
O1_2 C3_2 C4_2 120.0(7) . . ?
O2_2 C4_2 C3_2 125.5(8) . . ?
O2_2 C4_2 C5_2 120.6(9) . . ?
C3_2 C4_2 C5_2 113.9(7) . . ?
C10_2 C5_2 C6_2 117.4(8) . . ?
C10_2 C5_2 C4_2 121.8(8) . . ?
C6_2 C5_2 C4_2 120.7(8) . . ?
N1_2 C6_2 C7_2 119.3(8) . . ?
N1_2 C6_2 C5_2 119.6(8) . . ?
C7_2 C6_2 C5_2 121.1(9) . . ?
C8_2 C7_2 C6_2 119.6(8) . . ?
C8_2 C7_2 H7_2 120.2 . . ?
C6_2 C7_2 H7_2 120.2 . . ?
C7_2 C8_2 C9_2 120.9(9) . . ?
C7_2 C8_2 H8_2 119.6 . . ?
C9_2 C8_2 H8_2 119.6 . . ?
C10_2 C9_2 C8_2 119.5(10) . . ?
C10_2 C9_2 H9_2 120.2 . . ?
C8_2 C9_2 H9_2 120.2 . . ?
C9_2 C10_2 C5_2 121.5(9) . . ?
C9_2 C10_2 H10_2 119.3 . . ?
C5_2 C10_2 H10_2 119.3 . . ?
C12_2 C11_2 C21_2 129.7(10) . . ?
C12_2 C11_2 C16_2 113.7(10) . . ?
C21_2 C11_2 C16_2 116.5(9) . . ?
C11_2 C12_2 O1_2 117.2(9) . . ?
C11_2 C12_2 C13_2 120.0(9) . . ?
O1_2 C12_2 C13_2 122.8(8) . . ?
N14_2 C13_2 C12_2 126.2(10) . . ?
N14_2 C13_2 H13_2 116.9 . . ?
C12_2 C13_2 H13_2 116.9 . . ?
C13_2 N14_2 C15_2 117.3(10) . . ?
N14_2 C15_2 C16_2 120.4(9) . . ?
N14_2 C15_2 C20_2 120.4(12) . . ?
C16_2 C15_2 C20_2 119.2(11) . . ?
C17_2 C16_2 C15_2 115.7(11) . . ?
C17_2 C16_2 C11_2 122.4(12) . . ?
C15_2 C16_2 C11_2 121.7(9) . . ?
C18_2 C17_2 O3_2 116.2(12) . . ?
C18_2 C17_2 C16_2 127.1(14) . . ?
O3_2 C17_2 C16_2 116.7(12) . . ?
C17_2 C18_2 C19_2 114.9(12) . . ?
C17_2 C18_2 H18_2 122.5 . . ?
C19_2 C18_2 H18_2 122.5 . . ?
C20_2 C19_2 C18_2 123.4(13) . . ?
C20_2 C19_2 H19_2 118.3 . . ?
C18_2 C19_2 H19_2 118.3 . . ?
C19_2 C20_2 C15_2 119.2(14) . . ?
C19_2 C20_2 H20_2 120.4 . . ?
C15_2 C20_2 H20_2 120.4 . . ?
C22_2 C21_2 C11_2 117.6(12) . . ?
C22_2 C21_2 C26_2 115.2(12) . . ?
C11_2 C21_2 C26_2 127.1(9) . . ?
C23_2 C22_2 O3_2 119.3(15) . . ?
C23_2 C22_2 C21_2 119.3(16) . . ?
O3_2 C22_2 C21_2 121.4(12) . . ?
N24_2 C23_2 C22_2 127.0(17) . . ?
N24_2 C23_2 H23_2 116.5 . . ?
C22_2 C23_2 H23_2 116.5 . . ?
C23_2 N24_2 C25_2 115.6(14) . . ?
N24_2 C25_2 C30_2 117.7(16) . . ?
N24_2 C25_2 C26_2 123.4(16) . . ?
C30_2 C25_2 C26_2 118.6(17) . . ?
C25_2 C26_2 C21_2 117.2(13) . . ?
C25_2 C26_2 C27_2 118.1(14) . . ?
C21_2 C26_2 C27_2 124.6(10) . . ?
C28_2 C27_2 C26_2 123.1(12) . . ?
C28_2 C27_2 H27_2 118.4 . . ?
C26_2 C27_2 H27_2 118.4 . . ?
C27_2 C28_2 C29_2 118.1(14) . . ?
C27_2 C28_2 H28_2 121.0 . . ?
C29_2 C28_2 H28_2 121.0 . . ?
C28_2 C29_2 C30_2 119.7(14) . . ?
C28_2 C29_2 H29_2 120.2 . . ?
C30_2 C29_2 H29_2 120.2 . . ?
C25_2 C30_2 C29_2 122.2(16) . . ?
C25_2 C30_2 H30_2 118.9 . . ?
C29_2 C30_2 H30_2 118.9 . . ?
C3_2 O1_2 C12_2 120.7(7) . . ?
C4_2 O2_2 H2_2 109.5 . . ?
C22_2 O3_2 C17_2 121.5(10) . . ?

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_1 N1_1 C2_1 C3_1 -1.2(13) . . . . ?
N1_1 C2_1 C3_1 O1_1 167.9(8) . . . . ?
N1_1 C2_1 C3_1 C4_1 -0.8(15) . . . . ?
C2_1 C3_1 C4_1 O2_1 179.7(10) . . . . ?
O1_1 C3_1 C4_1 O2_1 11.6(16) . . . . ?
C2_1 C3_1 C4_1 C5_1 0.8(14) . . . . ?
O1_1 C3_1 C4_1 C5_1 -167.2(8) . . . . ?
O2_1 C4_1 C5_1 C6_1 -177.9(9) . . . . ?
C3_1 C4_1 C5_1 C6_1 1.0(13) . . . . ?
O2_1 C4_1 C5_1 C10_1 -2.8(15) . . . . ?
C3_1 C4_1 C5_1 C10_1 176.1(9) . . . . ?
C2_1 N1_1 C6_1 C7_1 -178.8(8) . . . . ?
C2_1 N1_1 C6_1 C5_1 3.1(13) . . . . ?
C10_1 C5_1 C6_1 N1_1 -178.3(9) . . . . ?
C4_1 C5_1 C6_1 N1_1 -3.0(13) . . . . ?
C10_1 C5_1 C6_1 C7_1 3.6(13) . . . . ?
C4_1 C5_1 C6_1 C7_1 178.9(9) . . . . ?
N1_1 C6_1 C7_1 C8_1 178.5(9) . . . . ?
C5_1 C6_1 C7_1 C8_1 -3.4(14) . . . . ?
C6_1 C7_1 C8_1 C9_1 0.8(14) . . . . ?
C7_1 C8_1 C9_1 C10_1 1.5(15) . . . . ?
C8_1 C9_1 C10_1 C5_1 -1.1(15) . . . . ?
C6_1 C5_1 C10_1 C9_1 -1.4(14) . . . . ?
C4_1 C5_1 C10_1 C9_1 -176.6(9) . . . . ?
C16_1 C11_1 C12_1 O1_1 -168.7(8) . . . . ?
C21_1 C11_1 C12_1 O1_1 5.1(14) . . . . ?
C16_1 C11_1 C12_1 C13_1 11.8(13) . . . . ?
C21_1 C11_1 C12_1 C13_1 -174.4(9) . . . . ?
O1_1 C12_1 C13_1 N14_1 176.8(9) . . . . ?
C11_1 C12_1 C13_1 N14_1 -3.7(16) . . . . ?
C12_1 C13_1 N14_1 C15_1 -4.9(16) . . . . ?
C13_1 N14_1 C15_1 C16_1 4.6(15) . . . . ?
C13_1 N14_1 C15_1 C20_1 -177.9(10) . . . . ?
N14_1 C15_1 C16_1 C11_1 3.9(15) . . . . ?
C20_1 C15_1 C16_1 C11_1 -173.6(9) . . . . ?
N14_1 C15_1 C16_1 C17_1 -173.4(9) . . . . ?
C20_1 C15_1 C16_1 C17_1 9.1(14) . . . . ?
C12_1 C11_1 C16_1 C15_1 -12.2(13) . . . . ?
C21_1 C11_1 C16_1 C15_1 173.3(9) . . . . ?
C12_1 C11_1 C16_1 C17_1 165.1(9) . . . . ?
C21_1 C11_1 C16_1 C17_1 -9.4(13) . . . . ?
C15_1 C16_1 C17_1 C18_1 -8.7(14) . . . . ?
C11_1 C16_1 C17_1 C18_1 174.0(9) . . . . ?
C15_1 C16_1 C17_1 O3_1 166.7(9) . . . . ?
C11_1 C16_1 C17_1 O3_1 -10.6(14) . . . . ?
O3_1 C17_1 C18_1 C19_1 -173.2(9) . . . . ?
C16_1 C17_1 C18_1 C19_1 2.2(15) . . . . ?
C17_1 C18_1 C19_1 C20_1 4.0(17) . . . . ?
C18_1 C19_1 C20_1 C15_1 -3.4(16) . . . . ?
N14_1 C15_1 C20_1 C19_1 179.2(10) . . . . ?
C16_1 C15_1 C20_1 C19_1 -3.2(16) . . . . ?
C12_1 C11_1 C21_1 C22_1 -154.4(10) . . . . ?
C16_1 C11_1 C21_1 C22_1 19.3(12) . . . . ?
C12_1 C11_1 C21_1 C26_1 29.0(16) . . . . ?
C16_1 C11_1 C21_1 C26_1 -157.3(9) . . . . ?
C26_1 C21_1 C22_1 O3_1 166.4(9) . . . . ?
C11_1 C21_1 C22_1 O3_1 -10.7(14) . . . . ?
C26_1 C21_1 C22_1 C23_1 -14.7(14) . . . . ?
C11_1 C21_1 C22_1 C23_1 168.2(9) . . . . ?
O3_1 C22_1 C23_1 N24_1 -175.4(9) . . . . ?
C21_1 C22_1 C23_1 N24_1 5.6(16) . . . . ?
C22_1 C23_1 N24_1 C25_1 5.3(15) . . . . ?
C23_1 N24_1 C25_1 C30_1 172.6(10) . . . . ?
C23_1 N24_1 C25_1 C26_1 -6.1(15) . . . . ?
N24_1 C25_1 C26_1 C27_1 170.1(9) . . . . ?
C30_1 C25_1 C26_1 C27_1 -8.6(14) . . . . ?
N24_1 C25_1 C26_1 C21_1 -3.6(14) . . . . ?
C30_1 C25_1 C26_1 C21_1 177.7(9) . . . . ?
C22_1 C21_1 C26_1 C27_1 -159.9(9) . . . . ?
C11_1 C21_1 C26_1 C27_1 16.8(15) . . . . ?
C22_1 C21_1 C26_1 C25_1 13.6(13) . . . . ?
C11_1 C21_1 C26_1 C25_1 -169.8(9) . . . . ?
C25_1 C26_1 C27_1 C28_1 7.0(14) . . . . ?
C21_1 C26_1 C27_1 C28_1 -179.6(9) . . . . ?
C26_1 C27_1 C28_1 C29_1 -1.3(15) . . . . ?
C27_1 C28_1 C29_1 C30_1 -2.9(16) . . . . ?
C28_1 C29_1 C30_1 C25_1 1.2(16) . . . . ?
N24_1 C25_1 C30_1 C29_1 -174.2(9) . . . . ?
C26_1 C25_1 C30_1 C29_1 4.6(16) . . . . ?
C11_1 C12_1 O1_1 C3_1 175.5(8) . . . . ?
C13_1 C12_1 O1_1 C3_1 -5.1(13) . . . . ?
C2_1 C3_1 O1_1 C12_1 124.7(9) . . . . ?
C4_1 C3_1 O1_1 C12_1 -66.4(12) . . . . ?
C21_1 C22_1 O3_1 C17_1 -9.3(14) . . . . ?
C23_1 C22_1 O3_1 C17_1 171.8(9) . . . . ?
C18_1 C17_1 O3_1 C22_1 -164.6(9) . . . . ?
C16_1 C17_1 O3_1 C22_1 20.0(13) . . . . ?
C6_2 N1_2 C2_2 C3_2 -0.1(13) . . . . ?
N1_2 C2_2 C3_2 O1_2 -169.7(8) . . . . ?
N1_2 C2_2 C3_2 C4_2 1.5(14) . . . . ?
C2_2 C3_2 C4_2 O2_2 178.9(9) . . . . ?
O1_2 C3_2 C4_2 O2_2 -10.3(14) . . . . ?
C2_2 C3_2 C4_2 C5_2 -1.7(13) . . . . ?
O1_2 C3_2 C4_2 C5_2 169.1(8) . . . . ?
O2_2 C4_2 C5_2 C10_2 2.5(14) . . . . ?
C3_2 C4_2 C5_2 C10_2 -176.9(9) . . . . ?
O2_2 C4_2 C5_2 C6_2 -179.9(8) . . . . ?
C3_2 C4_2 C5_2 C6_2 0.7(12) . . . . ?
C2_2 N1_2 C6_2 C7_2 177.7(8) . . . . ?
C2_2 N1_2 C6_2 C5_2 -0.8(12) . . . . ?
C10_2 C5_2 C6_2 N1_2 178.2(8) . . . . ?
C4_2 C5_2 C6_2 N1_2 0.5(13) . . . . ?
C10_2 C5_2 C6_2 C7_2 -0.3(13) . . . . ?
C4_2 C5_2 C6_2 C7_2 -178.0(9) . . . . ?
N1_2 C6_2 C7_2 C8_2 -178.1(8) . . . . ?
C5_2 C6_2 C7_2 C8_2 0.3(14) . . . . ?
C6_2 C7_2 C8_2 C9_2 0.2(14) . . . . ?
C7_2 C8_2 C9_2 C10_2 -0.7(15) . . . . ?
C8_2 C9_2 C10_2 C5_2 0.8(15) . . . . ?
C6_2 C5_2 C10_2 C9_2 -0.3(14) . . . . ?
C4_2 C5_2 C10_2 C9_2 177.4(9) . . . . ?
C21_2 C11_2 C12_2 O1_2 -7.7(16) . . . . ?
C16_2 C11_2 C12_2 O1_2 169.0(8) . . . . ?
C21_2 C11_2 C12_2 C13_2 174.8(10) . . . . ?
C16_2 C11_2 C12_2 C13_2 -8.4(13) . . . . ?
C11_2 C12_2 C13_2 N14_2 2.7(16) . . . . ?
O1_2 C12_2 C13_2 N14_2 -174.6(9) . . . . ?
C12_2 C13_2 N14_2 C15_2 3.1(16) . . . . ?
C13_2 N14_2 C15_2 C16_2 -2.3(15) . . . . ?
C13_2 N14_2 C15_2 C20_2 176.2(10) . . . . ?
N14_2 C15_2 C16_2 C17_2 170.9(10) . . . . ?
C20_2 C15_2 C16_2 C17_2 -7.5(15) . . . . ?
N14_2 C15_2 C16_2 C11_2 -4.1(16) . . . . ?
C20_2 C15_2 C16_2 C11_2 177.4(9) . . . . ?
C12_2 C11_2 C16_2 C17_2 -165.5(10) . . . . ?
C21_2 C11_2 C16_2 C17_2 11.7(14) . . . . ?
C12_2 C11_2 C16_2 C15_2 9.3(14) . . . . ?
C21_2 C11_2 C16_2 C15_2 -173.6(10) . . . . ?
C15_2 C16_2 C17_2 C18_2 8.9(17) . . . . ?
C11_2 C16_2 C17_2 C18_2 -176.0(11) . . . . ?
C15_2 C16_2 C17_2 O3_2 -169.0(10) . . . . ?
C11_2 C16_2 C17_2 O3_2 6.0(15) . . . . ?
O3_2 C17_2 C18_2 C19_2 172.5(11) . . . . ?
C16_2 C17_2 C18_2 C19_2 -5.4(19) . . . . ?
C17_2 C18_2 C19_2 C20_2 0.6(19) . . . . ?
C18_2 C19_2 C20_2 C15_2 0.0(19) . . . . ?
N14_2 C15_2 C20_2 C19_2 -174.8(11) . . . . ?
C16_2 C15_2 C20_2 C19_2 3.7(16) . . . . ?
C12_2 C11_2 C21_2 C22_2 156.2(10) . . . . ?
C16_2 C11_2 C21_2 C22_2 -20.4(14) . . . . ?
C12_2 C11_2 C21_2 C26_2 -28.4(18) . . . . ?
C16_2 C11_2 C21_2 C26_2 155.0(10) . . . . ?
C11_2 C21_2 C22_2 C23_2 -169.0(11) . . . . ?
C26_2 C21_2 C22_2 C23_2 15.0(15) . . . . ?
C11_2 C21_2 C22_2 O3_2 12.2(15) . . . . ?
C26_2 C21_2 C22_2 O3_2 -163.8(9) . . . . ?
O3_2 C22_2 C23_2 N24_2 175.1(13) . . . . ?
C21_2 C22_2 C23_2 N24_2 -4(2) . . . . ?
C22_2 C23_2 N24_2 C25_2 -6(2) . . . . ?
C23_2 N24_2 C25_2 C30_2 -169.3(13) . . . . ?
C23_2 N24_2 C25_2 C26_2 4(2) . . . . ?
N24_2 C25_2 C26_2 C21_2 7.2(17) . . . . ?
C30_2 C25_2 C26_2 C21_2 -179.3(11) . . . . ?
N24_2 C25_2 C26_2 C27_2 -169.7(11) . . . . ?
C30_2 C25_2 C26_2 C27_2 3.8(17) . . . . ?
C22_2 C21_2 C26_2 C25_2 -16.3(14) . . . . ?
C11_2 C21_2 C26_2 C25_2 168.2(11) . . . . ?
C22_2 C21_2 C26_2 C27_2 160.4(10) . . . . ?
C11_2 C21_2 C26_2 C27_2 -15.1(17) . . . . ?
C25_2 C26_2 C27_2 C28_2 0.4(16) . . . . ?
C21_2 C26_2 C27_2 C28_2 -176.2(10) . . . . ?
C26_2 C27_2 C28_2 C29_2 -4.0(16) . . . . ?
C27_2 C28_2 C29_2 C30_2 3.4(18) . . . . ?
N24_2 C25_2 C30_2 C29_2 169.5(12) . . . . ?
C26_2 C25_2 C30_2 C29_2 -4(2) . . . . ?
C28_2 C29_2 C30_2 C25_2 1(2) . . . . ?
C2_2 C3_2 O1_2 C12_2 -124.8(9) . . . . ?
C4_2 C3_2 O1_2 C12_2 63.6(11) . . . . ?
C11_2 C12_2 O1_2 C3_2 -170.2(8) . . . . ?
C13_2 C12_2 O1_2 C3_2 7.2(13) . . . . ?
C23_2 C22_2 O3_2 C17_2 -172.4(11) . . . . ?
C21_2 C22_2 O3_2 C17_2 6.5(15) . . . . ?
C18_2 C17_2 O3_2 C22_2 166.4(10) . . . . ?
C16_2 C17_2 O3_2 C22_2 -15.4(15) . . . . ?

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
O2_1 H2_1 O1_1 0.84 2.42 2.854(10) 112.7 . yes
O2_1 H2_1 N1_2 0.84 2.11 2.722(9) 129.9 1_455 yes
O2_2 H2_2 N1_1 0.84 2.11 2.716(9) 128.6 . yes
O2_2 H2_2 O1_2 0.84 2.41 2.844(9) 112.7 . yes

_refine_diff_density_max         0.605
_refine_diff_density_min         -0.313
_refine_diff_density_rms         0.087

