# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2024

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

data_chr15
_database_code_depnum_ccdc_archive 'CCDC 2295562'
loop_
_audit_author_name
_audit_author_address
'Frank Rominger'
;Heidelberg University
Germany
;
_audit_update_record             
;
2023-09-18 deposited with the CCDC.	2024-02-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            '5 in manuscript'
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H20 Cl2 N4 O4'
_chemical_formula_weight         379.24

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'
Cl Cl 0.3639 0.7018 '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                   5.1032(2)
_cell_length_b                   16.1333(4)
_cell_length_c                   21.3655(8)
_cell_angle_alpha                90
_cell_angle_beta                 92.657(3)
_cell_angle_gamma                90
_cell_volume                     1757.16(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    9006
_cell_measurement_theta_min      4.14
_cell_measurement_theta_max      64.56

_exptl_crystal_description       pole
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.434
_exptl_crystal_F_000             792
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.238
_exptl_crystal_size_mid          0.024
_exptl_crystal_size_min          0.021
_exptl_absorpt_coefficient_mu    3.565
_shelx_estimated_absorpt_T_min   0.484
_shelx_estimated_absorpt_T_max   0.929
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6563
_exptl_absorpt_correction_T_max  0.9473
_exptl_absorpt_process_details   'STOE X-AREA LANA'
_exptl_absorpt_special_details   'X-Area LANA 1.83.8.0 (STOE, 2020)'
_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Genix3D Cu HF'
_diffrn_measurement_device_type  'STOE Stadivari'
_diffrn_measurement_method       'rotation method, ω scans'
_diffrn_detector_area_resol_mean 5.81
_diffrn_reflns_number            10481
_diffrn_reflns_av_unetI/netI     0.0363
_diffrn_reflns_av_R_equivalents  0.0285
_diffrn_reflns_limit_h_min       -3
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         4.969
_diffrn_reflns_theta_max         64.273
_diffrn_reflns_theta_full        64.273
_diffrn_measured_fraction_theta_max 0.967
_diffrn_measured_fraction_theta_full 0.967
_diffrn_reflns_Laue_measured_fraction_max 0.967
_diffrn_reflns_Laue_measured_fraction_full 0.967
_diffrn_reflns_point_group_measured_fraction_max 0.967
_diffrn_reflns_point_group_measured_fraction_full 0.967
_reflns_number_total             2820
_reflns_number_gt                2132
_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       'X-Area Pilatus3_SV 1.31.170.0 (STOE, 2020)'
_computing_cell_refinement       'X-Area Recipe 1.36.0.0 (STOE, 2020)'
_computing_data_reduction        'X-Area Integrate 1.78.3.0 (STOE, 2020)'
_computing_structure_solution    'SHELXT-2014 (Sheldrick 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0484P)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         2820
_refine_ls_number_parameters     231
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0540
_refine_ls_R_factor_gt           0.0334
_refine_ls_wR_factor_ref         0.0835
_refine_ls_wR_factor_gt          0.0758
_refine_ls_goodness_of_fit_ref   0.992
_refine_ls_restrained_S_all      0.992
_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
Cl1 Cl 1.13036(10) 0.66696(3) 0.71200(3) 0.02877(17) Uani 1 1 d . . . . .
Cl2 Cl 0.23849(10) 0.51308(3) 0.55256(3) 0.02623(16) Uani 1 1 d . . . . .
N11 N 0.5576(3) 0.51904(11) 0.65076(9) 0.0231(4) Uani 1 1 d . . . . .
C12 C 0.7497(4) 0.55160(13) 0.68694(10) 0.0215(5) Uani 1 1 d . . . . .
N12 N 0.8130(4) 0.51389(12) 0.74470(9) 0.0267(5) Uani 1 1 d . . . . .
H12 H 0.964(5) 0.5106(15) 0.7566(12) 0.032(8) Uiso 1 1 d . . . . .
C13 C 0.8796(4) 0.62167(13) 0.66615(10) 0.0201(5) Uani 1 1 d . . . . .
N14 N 0.8207(3) 0.65827(11) 0.61200(8) 0.0212(4) Uani 1 1 d . . . . .
C15 C 0.6269(4) 0.62631(13) 0.57638(10) 0.0202(5) Uani 1 1 d . . . . .
N15 N 0.5591(4) 0.66489(11) 0.51936(9) 0.0230(4) Uani 1 1 d . . . . .
H15 H 0.407(5) 0.6633(14) 0.5056(12) 0.029(7) Uiso 1 1 d . . . . .
C16 C 0.4953(4) 0.55610(13) 0.59697(10) 0.0199(5) Uani 1 1 d . . . . .
C21 C 0.6229(4) 0.48613(14) 0.78307(11) 0.0256(5) Uani 1 1 d . . . . .
O21 O 0.3919(3) 0.49562(11) 0.77324(8) 0.0361(4) Uani 1 1 d . . . . .
O22 O 0.7376(3) 0.44894(11) 0.83318(8) 0.0383(5) Uani 1 1 d . . . . .
C23 C 0.5692(5) 0.41225(17) 0.88098(12) 0.0382(7) Uani 1 1 d . . . . .
C24 C 0.3994(6) 0.34518(16) 0.85120(16) 0.0524(8) Uani 1 1 d . . . . .
H24A H 0.315060 0.313710 0.883945 0.079 Uiso 1 1 calc R U . . .
H24B H 0.508189 0.307850 0.827199 0.079 Uiso 1 1 calc R U . . .
H24C H 0.264655 0.370418 0.823120 0.079 Uiso 1 1 calc R U . . .
C25 C 0.4137(6) 0.47998(18) 0.91096(14) 0.0488(8) Uani 1 1 d . . . . .
H25A H 0.332053 0.457993 0.948121 0.073 Uiso 1 1 calc R U . . .
H25B H 0.277151 0.500054 0.880954 0.073 Uiso 1 1 calc R U . . .
H25C H 0.531081 0.525827 0.923274 0.073 Uiso 1 1 calc R U . . .
C26 C 0.7678(6) 0.3749(3) 0.92790(18) 0.0981(17) Uani 1 1 d . . . . .
H26A H 0.675608 0.348162 0.961701 0.147 Uiso 1 1 calc R U . . .
H26B H 0.881990 0.418757 0.945439 0.147 Uiso 1 1 calc R U . . .
H26C H 0.873949 0.333686 0.906876 0.147 Uiso 1 1 calc R U . . .
C31 C 0.7451(4) 0.68970(13) 0.47860(11) 0.0238(5) Uani 1 1 d . . . . .
O31 O 0.9789(3) 0.68471(10) 0.48890(8) 0.0304(4) Uani 1 1 d . . . . .
O32 O 0.6240(3) 0.71957(11) 0.42659(7) 0.0340(4) Uani 1 1 d . . . . .
C33 C 0.7847(4) 0.74571(16) 0.37359(12) 0.0331(6) Uani 1 1 d . . . . .
C34 C 0.9314(5) 0.67224(17) 0.34888(13) 0.0407(7) Uani 1 1 d . . . . .
H34A H 1.009430 0.687357 0.309406 0.061 Uiso 1 1 calc R U . . .
H34B H 0.809592 0.625901 0.341595 0.061 Uiso 1 1 calc R U . . .
H34C H 1.070280 0.655787 0.379588 0.061 Uiso 1 1 calc R U . . .
C35 C 0.5770(5) 0.7753(2) 0.32547(14) 0.0628(10) Uani 1 1 d . . . . .
H35A H 0.661838 0.794869 0.287985 0.094 Uiso 1 1 calc R U . . .
H35B H 0.476973 0.820808 0.343220 0.094 Uiso 1 1 calc R U . . .
H35C H 0.458174 0.729453 0.314174 0.094 Uiso 1 1 calc R U . . .
C36 C 0.9585(5) 0.81771(16) 0.39404(13) 0.0402(7) Uani 1 1 d . . . . .
H36A H 1.024927 0.845114 0.357042 0.060 Uiso 1 1 calc R U . . .
H36B H 1.106288 0.797222 0.420599 0.060 Uiso 1 1 calc R U . . .
H36C H 0.856722 0.857398 0.417740 0.060 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C13 1.736(2) . ?
Cl2 C16 1.727(2) . ?
N11 C16 1.321(3) . ?
N11 C12 1.328(3) . ?
C12 C13 1.393(3) . ?
C12 N12 1.400(3) . ?
N12 C21 1.374(3) . ?
N12 H12 0.80(3) . ?
C13 N14 1.321(3) . ?
N14 C15 1.324(3) . ?
C15 N15 1.397(3) . ?
C15 C16 1.398(3) . ?
N15 C31 1.377(3) . ?
N15 H15 0.82(3) . ?
C21 O21 1.198(3) . ?
C21 O22 1.338(3) . ?
O22 C23 1.488(3) . ?
C23 C24 1.508(4) . ?
C23 C25 1.510(4) . ?
C23 C26 1.517(4) . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C31 O31 1.206(2) . ?
C31 O32 1.336(3) . ?
O32 C33 1.490(3) . ?
C33 C34 1.510(4) . ?
C33 C36 1.513(4) . ?
C33 C35 1.519(3) . ?
C34 H34A 0.9800 . ?
C34 H34B 0.9800 . ?
C34 H34C 0.9800 . ?
C35 H35A 0.9800 . ?
C35 H35B 0.9800 . ?
C35 H35C 0.9800 . ?
C36 H36A 0.9800 . ?
C36 H36B 0.9800 . ?
C36 H36C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C16 N11 C12 117.95(19) . . ?
N11 C12 C13 119.0(2) . . ?
N11 C12 N12 118.34(19) . . ?
C13 C12 N12 122.68(19) . . ?
C21 N12 C12 121.8(2) . . ?
C21 N12 H12 119.0(19) . . ?
C12 N12 H12 119.1(19) . . ?
N14 C13 C12 123.33(19) . . ?
N14 C13 Cl1 115.97(16) . . ?
C12 C13 Cl1 120.69(16) . . ?
C13 N14 C15 117.57(19) . . ?
N14 C15 N15 118.42(19) . . ?
N14 C15 C16 119.44(19) . . ?
N15 C15 C16 122.14(19) . . ?
C31 N15 C15 122.06(19) . . ?
C31 N15 H15 116.9(18) . . ?
C15 N15 H15 119.5(18) . . ?
N11 C16 C15 122.71(19) . . ?
N11 C16 Cl2 116.22(16) . . ?
C15 C16 Cl2 121.07(16) . . ?
O21 C21 O22 126.0(2) . . ?
O21 C21 N12 124.8(2) . . ?
O22 C21 N12 109.21(19) . . ?
C21 O22 C23 118.86(17) . . ?
O22 C23 C24 109.5(2) . . ?
O22 C23 C25 109.6(2) . . ?
C24 C23 C25 113.3(2) . . ?
O22 C23 C26 102.86(19) . . ?
C24 C23 C26 110.3(3) . . ?
C25 C23 C26 110.8(3) . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C23 C25 H25A 109.5 . . ?
C23 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C23 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C23 C26 H26A 109.5 . . ?
C23 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C23 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
O31 C31 O32 126.3(2) . . ?
O31 C31 N15 124.8(2) . . ?
O32 C31 N15 108.97(18) . . ?
C31 O32 C33 118.98(17) . . ?
O32 C33 C34 110.1(2) . . ?
O32 C33 C36 109.5(2) . . ?
C34 C33 C36 114.2(2) . . ?
O32 C33 C35 102.23(18) . . ?
C34 C33 C35 110.6(3) . . ?
C36 C33 C35 109.6(2) . . ?
C33 C34 H34A 109.5 . . ?
C33 C34 H34B 109.5 . . ?
H34A C34 H34B 109.5 . . ?
C33 C34 H34C 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
C33 C35 H35A 109.5 . . ?
C33 C35 H35B 109.5 . . ?
H35A C35 H35B 109.5 . . ?
C33 C35 H35C 109.5 . . ?
H35A C35 H35C 109.5 . . ?
H35B C35 H35C 109.5 . . ?
C33 C36 H36A 109.5 . . ?
C33 C36 H36B 109.5 . . ?
H36A C36 H36B 109.5 . . ?
C33 C36 H36C 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C16 N11 C12 C13 -1.4(3) . . . . ?
C16 N11 C12 N12 178.51(19) . . . . ?
N11 C12 N12 C21 -42.1(3) . . . . ?
C13 C12 N12 C21 137.7(2) . . . . ?
N11 C12 C13 N14 0.4(3) . . . . ?
N12 C12 C13 N14 -179.5(2) . . . . ?
N11 C12 C13 Cl1 179.52(16) . . . . ?
N12 C12 C13 Cl1 -0.4(3) . . . . ?
C12 C13 N14 C15 0.4(3) . . . . ?
Cl1 C13 N14 C15 -178.72(15) . . . . ?
C13 N14 C15 N15 179.05(19) . . . . ?
C13 N14 C15 C16 -0.3(3) . . . . ?
N14 C15 N15 C31 45.7(3) . . . . ?
C16 C15 N15 C31 -135.0(2) . . . . ?
C12 N11 C16 C15 1.6(3) . . . . ?
C12 N11 C16 Cl2 -178.30(16) . . . . ?
N14 C15 C16 N11 -0.7(3) . . . . ?
N15 C15 C16 N11 179.97(19) . . . . ?
N14 C15 C16 Cl2 179.12(15) . . . . ?
N15 C15 C16 Cl2 -0.2(3) . . . . ?
C12 N12 C21 O21 -4.7(4) . . . . ?
C12 N12 C21 O22 176.6(2) . . . . ?
O21 C21 O22 C23 2.6(4) . . . . ?
N12 C21 O22 C23 -178.8(2) . . . . ?
C21 O22 C23 C24 61.1(3) . . . . ?
C21 O22 C23 C25 -63.7(3) . . . . ?
C21 O22 C23 C26 178.4(3) . . . . ?
C15 N15 C31 O31 -3.9(3) . . . . ?
C15 N15 C31 O32 176.06(19) . . . . ?
O31 C31 O32 C33 3.6(3) . . . . ?
N15 C31 O32 C33 -176.29(19) . . . . ?
C31 O32 C33 C34 62.8(3) . . . . ?
C31 O32 C33 C36 -63.6(3) . . . . ?
C31 O32 C33 C35 -179.7(2) . . . . ?

_refine_diff_density_max         0.254
_refine_diff_density_min         -0.236
_refine_diff_density_rms         0.048


####################################################################### 
# 
# 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_juk20
_database_code_depnum_ccdc_archive 'CCDC 2312913'
loop_
_audit_author_name
_audit_author_address
'Frank Rominger'
;Heidelberg University
Germany
;
_audit_update_record             
;
2023-12-08 deposited with the CCDC.	2024-02-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C28 H16 F6 N4'
_chemical_formula_weight         522.45

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'
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/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                   13.546(3)
_cell_length_b                   11.813(3)
_cell_length_c                   7.2637(17)
_cell_angle_alpha                90
_cell_angle_beta                 102.679(7)
_cell_angle_gamma                90
_cell_volume                     1133.9(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    1391
_cell_measurement_theta_min      2.31
_cell_measurement_theta_max      20.72

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.530
_exptl_crystal_F_000             532
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.090
_exptl_crystal_size_mid          0.038
_exptl_crystal_size_min          0.012
_exptl_absorpt_coefficient_mu    0.127
_shelx_estimated_absorpt_T_min   0.989
_shelx_estimated_absorpt_T_max   0.998
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.864695
_exptl_absorpt_correction_T_max  0.958973
_exptl_absorpt_process_details   
;
Sheldrick, G. M. (2008). SADABS. University of Göttingen, Germany.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'ImuS microsource'
_diffrn_measurement_device_type  'Bruker APEX-II Quazar area detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11733
_diffrn_reflns_av_unetI/netI     0.1298
_diffrn_reflns_av_R_equivalents  0.1071
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         1.541
_diffrn_reflns_theta_max         27.585
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.953
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.953
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.953
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2497
_reflns_number_gt                1364
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT-2018/2 (Sheldrick 2015)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
; 
 Refined as a 2-component twin. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0451P)²+0.5782P] 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         2497
_refine_ls_number_parameters     173
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1716
_refine_ls_R_factor_gt           0.0717
_refine_ls_wR_factor_ref         0.1479
_refine_ls_wR_factor_gt          0.1177
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_restrained_S_all      1.059
_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 0.6276(3) 0.4673(3) 0.6750(5) 0.0280(9) Uani 1 1 d . . . . .
C2 C 0.5608(3) 0.3897(3) 0.7158(5) 0.0275(9) Uani 1 1 d . . . . .
H2 H 0.543945 0.319393 0.653332 0.033 Uiso 1 1 calc R U . . .
C3 C 0.5210(3) 0.4316(3) 0.8666(5) 0.0250(9) Uani 1 1 d . . . . .
C5 C 0.4345(3) 0.4588(3) 1.0892(5) 0.0251(9) Uani 1 1 d . . . . .
N6 N 0.3702(2) 0.4391(3) 1.2071(4) 0.0275(8) Uani 1 1 d . . . . .
C7 C 0.3211(3) 0.3292(3) 1.2143(5) 0.0310(10) Uani 1 1 d . . . . .
H7A H 0.367786 0.268674 1.192341 0.037 Uiso 1 1 calc R U . . .
H7B H 0.308474 0.318179 1.342239 0.037 Uiso 1 1 calc R U . . .
C8 C 0.2256(3) 0.3179(3) 1.0759(6) 0.0322(10) Uani 1 1 d . . . . .
N4 N 0.4532(2) 0.3876(3) 0.9600(4) 0.0280(8) Uani 1 1 d . . . . .
C9 C 0.1479(4) 0.3079(4) 0.9687(7) 0.0472(12) Uani 1 1 d . . . . .
H9 H 0.084753 0.299791 0.881627 0.057 Uiso 1 1 calc R U . . .
F11 F 0.9148(2) 0.2741(2) 0.1786(4) 0.0684(9) Uani 1 1 d . . . . .
C11 C 0.6919(3) 0.4547(3) 0.5377(5) 0.0277(9) Uani 1 1 d . . . . .
F12 F 0.8354(2) 0.3871(2) -0.0270(3) 0.0607(9) Uani 1 1 d . . . . .
C12 C 0.6581(3) 0.3868(3) 0.3812(5) 0.0329(10) Uani 1 1 d . . . . .
H12 H 0.592082 0.355084 0.360138 0.040 Uiso 1 1 calc R U . . .
F13 F 0.9633(2) 0.4447(2) 0.1746(4) 0.0668(9) Uani 1 1 d . . . . .
C13 C 0.7183(3) 0.3643(3) 0.2555(5) 0.0334(10) Uani 1 1 d . . . . .
H13 H 0.693841 0.316928 0.149538 0.040 Uiso 1 1 calc R U . . .
C14 C 0.8143(3) 0.4105(3) 0.2831(5) 0.0307(10) Uani 1 1 d . . . . .
C15 C 0.8479(3) 0.4803(3) 0.4356(5) 0.0350(11) Uani 1 1 d . . . . .
H15 H 0.912686 0.514556 0.452512 0.042 Uiso 1 1 calc R U . . .
C16 C 0.7889(3) 0.5013(3) 0.5640(5) 0.0339(10) Uani 1 1 d . . . . .
H16 H 0.814184 0.547604 0.670877 0.041 Uiso 1 1 calc R U . . .
C18 C 0.8813(3) 0.3811(4) 0.1540(6) 0.0394(11) 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 C2 1.366(5) . ?
C1 N6 1.394(4) 3_667 ?
C1 C11 1.468(5) . ?
C2 C3 1.412(5) . ?
C2 H2 0.9500 . ?
C3 N4 1.360(4) . ?
C3 C5 1.434(5) 3_667 ?
C5 N4 1.326(4) . ?
C5 N6 1.368(4) . ?
N6 C7 1.465(4) . ?
C7 C8 1.461(6) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.170(6) . ?
C9 H9 0.9500 . ?
F11 C18 1.342(5) . ?
C11 C12 1.385(5) . ?
C11 C16 1.398(5) . ?
F12 C18 1.327(4) . ?
C12 C13 1.377(5) . ?
C12 H12 0.9500 . ?
F13 C18 1.321(5) . ?
C13 C14 1.384(5) . ?
C13 H13 0.9500 . ?
C14 C15 1.375(5) . ?
C14 C18 1.483(5) . ?
C15 C16 1.378(5) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 N6 108.9(3) . 3_667 ?
C2 C1 C11 126.8(4) . . ?
N6 C1 C11 124.2(3) 3_667 . ?
C1 C2 C3 108.5(3) . . ?
C1 C2 H2 125.8 . . ?
C3 C2 H2 125.8 . . ?
N4 C3 C2 131.9(3) . . ?
N4 C3 C5 122.0(3) . 3_667 ?
C2 C3 C5 106.1(3) . 3_667 ?
N4 C5 N6 125.6(3) . . ?
N4 C5 C3 126.5(3) . 3_667 ?
N6 C5 C3 107.9(3) . 3_667 ?
C5 N6 C1 108.6(3) . 3_667 ?
C5 N6 C7 121.9(3) . . ?
C1 N6 C7 129.0(3) 3_667 . ?
C8 C7 N6 113.4(3) . . ?
C8 C7 H7A 108.9 . . ?
N6 C7 H7A 108.9 . . ?
C8 C7 H7B 108.9 . . ?
N6 C7 H7B 108.9 . . ?
H7A C7 H7B 107.7 . . ?
C9 C8 C7 178.3(4) . . ?
C5 N4 C3 111.4(3) . . ?
C8 C9 H9 180.0 . . ?
C12 C11 C16 118.2(4) . . ?
C12 C11 C1 118.5(3) . . ?
C16 C11 C1 123.1(4) . . ?
C13 C12 C11 121.2(4) . . ?
C13 C12 H12 119.4 . . ?
C11 C12 H12 119.4 . . ?
C12 C13 C14 120.1(4) . . ?
C12 C13 H13 119.9 . . ?
C14 C13 H13 119.9 . . ?
C15 C14 C13 119.2(4) . . ?
C15 C14 C18 120.6(4) . . ?
C13 C14 C18 120.2(4) . . ?
C14 C15 C16 121.0(4) . . ?
C14 C15 H15 119.5 . . ?
C16 C15 H15 119.5 . . ?
C15 C16 C11 120.3(4) . . ?
C15 C16 H16 119.9 . . ?
C11 C16 H16 119.9 . . ?
F13 C18 F12 106.4(4) . . ?
F13 C18 F11 105.6(4) . . ?
F12 C18 F11 104.7(4) . . ?
F13 C18 C14 114.3(4) . . ?
F12 C18 C14 113.3(3) . . ?
F11 C18 C14 111.9(4) . . ?

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
N6 C1 C2 C3 -1.8(4) 3_667 . . . ?
C11 C1 C2 C3 175.1(4) . . . . ?
C1 C2 C3 N4 -179.6(4) . . . . ?
C1 C2 C3 C5 1.8(4) . . . 3_667 ?
N4 C5 N6 C1 178.8(3) . . . 3_667 ?
C3 C5 N6 C1 0.0(4) 3_667 . . 3_667 ?
N4 C5 N6 C7 6.0(6) . . . . ?
C3 C5 N6 C7 -172.8(3) 3_667 . . . ?
C5 N6 C7 C8 -87.4(4) . . . . ?
C1 N6 C7 C8 101.4(4) 3_667 . . . ?
N6 C5 N4 C3 -179.5(3) . . . . ?
C3 C5 N4 C3 -1.0(6) 3_667 . . . ?
C2 C3 N4 C5 -177.5(4) . . . . ?
C5 C3 N4 C5 0.9(5) 3_667 . . . ?
C2 C1 C11 C12 29.4(6) . . . . ?
N6 C1 C11 C12 -154.1(4) 3_667 . . . ?
C2 C1 C11 C16 -145.8(4) . . . . ?
N6 C1 C11 C16 30.7(6) 3_667 . . . ?
C16 C11 C12 C13 0.7(6) . . . . ?
C1 C11 C12 C13 -174.7(4) . . . . ?
C11 C12 C13 C14 -0.5(6) . . . . ?
C12 C13 C14 C15 -1.0(6) . . . . ?
C12 C13 C14 C18 176.5(4) . . . . ?
C13 C14 C15 C16 2.4(6) . . . . ?
C18 C14 C15 C16 -175.2(4) . . . . ?
C14 C15 C16 C11 -2.2(6) . . . . ?
C12 C11 C16 C15 0.6(6) . . . . ?
C1 C11 C16 C15 175.8(4) . . . . ?
C15 C14 C18 F13 -13.5(6) . . . . ?
C13 C14 C18 F13 169.0(4) . . . . ?
C15 C14 C18 F12 -135.6(4) . . . . ?
C13 C14 C18 F12 46.9(6) . . . . ?
C15 C14 C18 F11 106.4(4) . . . . ?
C13 C14 C18 F11 -71.1(5) . . . . ?

_refine_diff_density_max         0.270
_refine_diff_density_min         -0.369
_refine_diff_density_rms         0.073




#==================================================================


####################################################################### 
# 
# 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_juk13
_database_code_depnum_ccdc_archive 'CCDC 2295563'
loop_
_audit_author_name
_audit_author_address
'Frank Rominger'
;Heidelberg University
Germany
;
_audit_update_record             
;
2023-09-18 deposited with the CCDC.	2024-02-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            'BAPY-a in manuscript'
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C32 H34 N4 O6'
_chemical_formula_weight         570.63

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/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                   13.620(2)
_cell_length_b                   5.1428(8)
_cell_length_c                   22.255(4)
_cell_angle_alpha                90
_cell_angle_beta                 107.679(4)
_cell_angle_gamma                90
_cell_volume                     1485.2(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    1289
_cell_measurement_theta_min      2.83
_cell_measurement_theta_max      19.13

_exptl_crystal_description       plank
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.276
_exptl_crystal_F_000             604
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.037
_exptl_crystal_size_min          0.012
_exptl_absorpt_coefficient_mu    0.089
_shelx_estimated_absorpt_T_min   0.982
_shelx_estimated_absorpt_T_max   0.999
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9015
_exptl_absorpt_correction_T_max  0.9575
_exptl_absorpt_process_details   
;
Sheldrick, G. M. (2008). SADABS. University of Göttingen, Germany.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'ImuS microsource'
_diffrn_measurement_device_type  'Bruker APEX-II Quazar area detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15099
_diffrn_reflns_av_unetI/netI     0.0792
_diffrn_reflns_av_R_equivalents  0.1181
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         1.571
_diffrn_reflns_theta_max         22.975
_diffrn_reflns_theta_full        22.975
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2063
_reflns_number_gt                1272
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT-2018/2 (Sheldrick 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0318P)²+1.3074P] 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         2063
_refine_ls_number_parameters     197
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1140
_refine_ls_R_factor_gt           0.0556
_refine_ls_wR_factor_ref         0.1197
_refine_ls_wR_factor_gt          0.1003
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.048
_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 0.4244(3) -0.0512(7) 0.52415(16) 0.0228(9) Uani 1 1 d . . . . .
N1 N 0.3456(2) -0.1081(6) 0.55091(14) 0.0245(8) Uani 1 1 d . . . . .
H1 H 0.337(3) -0.275(7) 0.5602(16) 0.037 Uiso 1 1 d . U . . .
N2 N 0.4015(2) 0.1069(6) 0.47491(13) 0.0256(8) Uani 1 1 d . . . . .
C3 C 0.4783(3) 0.1619(7) 0.45009(16) 0.0251(9) Uani 1 1 d . . . . .
C4 C 0.4553(3) 0.3280(8) 0.39619(18) 0.0288(10) Uani 1 1 d . . . . .
C5 C 0.4400(3) 0.4578(8) 0.35022(19) 0.0330(10) Uani 1 1 d . . . . .
O6 O 0.30198(18) 0.3139(5) 0.56185(11) 0.0306(7) Uani 1 1 d . . . . .
C6 C 0.2885(3) 0.0836(8) 0.56728(16) 0.0247(9) Uani 1 1 d . . . . .
O7 O 0.21892(18) -0.0245(5) 0.59091(12) 0.0336(7) Uani 1 1 d . . . . .
C7 C 0.1509(3) 0.1457(7) 0.61516(18) 0.0296(10) Uani 1 1 d . . . . .
C8 C 0.0853(3) -0.0500(8) 0.6371(2) 0.0565(14) Uani 1 1 d . . . . .
H8A H 0.036336 0.042666 0.653790 0.085 Uiso 1 1 calc R U . . .
H8B H 0.129885 -0.160063 0.670207 0.085 Uiso 1 1 calc R U . . .
H8C H 0.047418 -0.158728 0.601413 0.085 Uiso 1 1 calc R U . . .
C9 C 0.2165(3) 0.3012(8) 0.67054(18) 0.0434(11) Uani 1 1 d . . . . .
H9A H 0.171873 0.392840 0.690776 0.065 Uiso 1 1 calc R U . . .
H9B H 0.257625 0.427864 0.655670 0.065 Uiso 1 1 calc R U . . .
H9C H 0.262471 0.183635 0.701042 0.065 Uiso 1 1 calc R U . . .
C10 C 0.0847(3) 0.3092(8) 0.56204(18) 0.0412(11) Uani 1 1 d . . . . .
H10A H 0.028493 0.387117 0.574898 0.062 Uiso 1 1 calc R U . . .
H10B H 0.055784 0.199717 0.524812 0.062 Uiso 1 1 calc R U . . .
H10C H 0.126644 0.447207 0.551872 0.062 Uiso 1 1 calc R U . . .
C11 C 0.4227(3) 0.6129(7) 0.29394(16) 0.0270(9) Uani 1 1 d . . . . .
C12 C 0.3442(3) 0.5635(7) 0.23863(17) 0.0318(10) Uani 1 1 d . . . . .
H12 H 0.298561 0.422551 0.237324 0.038 Uiso 1 1 calc R U . . .
C13 C 0.3309(3) 0.7139(7) 0.18552(17) 0.0313(10) Uani 1 1 d . . . . .
H13 H 0.276743 0.676210 0.148088 0.038 Uiso 1 1 calc R U . . .
C14 C 0.3968(3) 0.9197(7) 0.18697(17) 0.0271(9) Uani 1 1 d . . . . .
C15 C 0.4754(3) 0.9742(7) 0.24115(18) 0.0339(10) Uani 1 1 d . . . . .
H15 H 0.520653 1.115729 0.242050 0.041 Uiso 1 1 calc R U . . .
C16 C 0.4882(3) 0.8229(8) 0.29407(17) 0.0357(11) Uani 1 1 d . . . . .
H16 H 0.542443 0.861810 0.331358 0.043 Uiso 1 1 calc R U . . .
O18 O 0.39086(19) 1.0806(5) 0.13731(12) 0.0391(7) Uani 1 1 d . . . . .
C18 C 0.3065(3) 1.0510(10) 0.08162(18) 0.0639(15) Uani 1 1 d . . . . .
H18A H 0.311752 1.179951 0.050331 0.096 Uiso 1 1 calc R U . . .
H18B H 0.241822 1.076684 0.091546 0.096 Uiso 1 1 calc R U . . .
H18C H 0.307673 0.875754 0.064532 0.096 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
C1 N2 1.323(4) . ?
C1 C3 1.395(5) 3_656 ?
C1 N1 1.407(4) . ?
N1 C6 1.372(4) . ?
N1 H1 0.90(4) . ?
N2 C3 1.352(4) . ?
C3 C4 1.428(5) . ?
C4 C5 1.186(5) . ?
C5 C11 1.443(5) . ?
O6 C6 1.210(4) . ?
C6 O7 1.337(4) . ?
O7 C7 1.490(4) . ?
C7 C10 1.507(5) . ?
C7 C9 1.513(5) . ?
C7 C8 1.521(5) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 C12 1.387(5) . ?
C11 C16 1.400(5) . ?
C12 C13 1.378(5) . ?
C12 H12 0.9500 . ?
C13 C14 1.381(5) . ?
C13 H13 0.9500 . ?
C14 O18 1.363(4) . ?
C14 C15 1.376(5) . ?
C15 C16 1.378(5) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
O18 C18 1.419(4) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 C1 C3 123.1(3) . 3_656 ?
N2 C1 N1 117.4(3) . . ?
C3 C1 N1 119.5(3) 3_656 . ?
C6 N1 C1 122.0(3) . . ?
C6 N1 H1 120(2) . . ?
C1 N1 H1 117(2) . . ?
C1 N2 C3 116.7(3) . . ?
N2 C3 C1 120.2(3) . 3_656 ?
N2 C3 C4 118.0(3) . . ?
C1 C3 C4 121.9(3) 3_656 . ?
C5 C4 C3 176.3(4) . . ?
C4 C5 C11 178.9(4) . . ?
O6 C6 O7 126.4(3) . . ?
O6 C6 N1 124.2(3) . . ?
O7 C6 N1 109.4(3) . . ?
C6 O7 C7 119.4(3) . . ?
O7 C7 C10 109.5(3) . . ?
O7 C7 C9 109.1(3) . . ?
C10 C7 C9 114.1(3) . . ?
O7 C7 C8 102.6(3) . . ?
C10 C7 C8 110.6(3) . . ?
C9 C7 C8 110.3(3) . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C7 C9 H9A 109.5 . . ?
C7 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C7 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C7 C10 H10A 109.5 . . ?
C7 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C7 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C12 C11 C16 117.5(3) . . ?
C12 C11 C5 123.2(4) . . ?
C16 C11 C5 119.3(3) . . ?
C13 C12 C11 121.6(4) . . ?
C13 C12 H12 119.2 . . ?
C11 C12 H12 119.2 . . ?
C12 C13 C14 119.6(4) . . ?
C12 C13 H13 120.2 . . ?
C14 C13 H13 120.2 . . ?
O18 C14 C15 115.2(3) . . ?
O18 C14 C13 124.6(3) . . ?
C15 C14 C13 120.2(3) . . ?
C14 C15 C16 119.8(4) . . ?
C14 C15 H15 120.1 . . ?
C16 C15 H15 120.1 . . ?
C15 C16 C11 121.3(4) . . ?
C15 C16 H16 119.4 . . ?
C11 C16 H16 119.4 . . ?
C14 O18 C18 118.4(3) . . ?
O18 C18 H18A 109.5 . . ?
O18 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
O18 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N2 C1 N1 C6 -50.9(5) . . . . ?
C3 C1 N1 C6 129.3(4) 3_656 . . . ?
C3 C1 N2 C3 -0.8(6) 3_656 . . . ?
N1 C1 N2 C3 179.4(3) . . . . ?
C1 N2 C3 C1 0.8(6) . . . 3_656 ?
C1 N2 C3 C4 178.8(3) . . . . ?
C1 N1 C6 O6 -1.9(5) . . . . ?
C1 N1 C6 O7 179.4(3) . . . . ?
O6 C6 O7 C7 -1.7(5) . . . . ?
N1 C6 O7 C7 177.0(3) . . . . ?
C6 O7 C7 C10 62.6(4) . . . . ?
C6 O7 C7 C9 -62.9(4) . . . . ?
C6 O7 C7 C8 -180.0(3) . . . . ?
C16 C11 C12 C13 0.2(5) . . . . ?
C5 C11 C12 C13 -179.1(4) . . . . ?
C11 C12 C13 C14 -0.2(6) . . . . ?
C12 C13 C14 O18 179.9(3) . . . . ?
C12 C13 C14 C15 0.1(5) . . . . ?
O18 C14 C15 C16 -179.9(3) . . . . ?
C13 C14 C15 C16 -0.1(6) . . . . ?
C14 C15 C16 C11 0.2(6) . . . . ?
C12 C11 C16 C15 -0.2(5) . . . . ?
C5 C11 C16 C15 179.2(4) . . . . ?
C15 C14 O18 C18 -174.6(4) . . . . ?
C13 C14 O18 C18 5.6(5) . . . . ?

_refine_diff_density_max         0.201
_refine_diff_density_min         -0.238
_refine_diff_density_rms         0.052



# start Validation Reply Form
_vrf_THETM01_juk13               
;
PROBLEM: The value of sine(theta_max)/wavelength is less than 0.550
RESPONSE: We have cut the dataset at a resolution of 0.91 A due to 
I/sigma and R(int) criteria. Despite of using a high intensity source 
and long irradiation times this was the best achievable resolution. 
The data to parameter ratio is still acceptable. 
;
####################################################################### 
# 
# 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_juk15
_database_code_depnum_ccdc_archive 'CCDC 2295564'
loop_
_audit_author_name
_audit_author_address
'Frank Rominger'
;Heidelberg University
Germany
;
_audit_update_record             
;
2023-09-18 deposited with the CCDC.	2024-02-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            'BOCPY_b in manuscript'
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C33 H29 Cl3 F6 N4 O4'
_chemical_formula_weight         765.95

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'
Cl Cl 0.1484 0.1585 '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                   10.1680(7)
_cell_length_b                   10.8563(7)
_cell_length_c                   18.1982(13)
_cell_angle_alpha                89.6490(10)
_cell_angle_beta                 77.6690(10)
_cell_angle_gamma                65.2990(10)
_cell_volume                     1775.1(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    5963
_cell_measurement_theta_min      2.27
_cell_measurement_theta_max      23.61

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.433
_exptl_crystal_F_000             784
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.126
_exptl_crystal_size_mid          0.077
_exptl_crystal_size_min          0.055
_exptl_absorpt_coefficient_mu    0.332
_shelx_estimated_absorpt_T_min   0.959
_shelx_estimated_absorpt_T_max   0.982
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.711
_exptl_absorpt_correction_T_max  0.745
_exptl_absorpt_process_details   
;
Sheldrick, G. M. (2008). SADABS. University of Göttingen, Germany.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            28765
_diffrn_reflns_av_unetI/netI     0.0463
_diffrn_reflns_av_R_equivalents  0.0525
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.074
_diffrn_reflns_theta_max         25.466
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             6566
_reflns_number_gt                4404
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0514P)²+1.9232P] 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         6566
_refine_ls_number_parameters     541
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0951
_refine_ls_R_factor_gt           0.0590
_refine_ls_wR_factor_ref         0.1501
_refine_ls_wR_factor_gt          0.1286
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_restrained_S_all      1.032
_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
N1 N 0.3145(2) 0.4684(2) 0.38877(11) 0.0260(5) Uani 1 1 d . . . . .
C2 C 0.2986(3) 0.3694(3) 0.42684(13) 0.0241(6) Uani 1 1 d . . . . .
N3 N 0.2241(2) 0.3802(2) 0.50254(11) 0.0259(5) Uani 1 1 d . . . . .
C4 C 0.2447(3) 0.2477(3) 0.52096(14) 0.0273(6) Uani 1 1 d . . . . .
C5 C 0.3271(3) 0.1573(3) 0.45957(15) 0.0308(6) Uani 1 1 d . . . . .
H5 H 0.356198 0.061789 0.457284 0.037 Uiso 1 1 calc R U . . .
C6 C 0.3624(3) 0.2304(3) 0.39927(14) 0.0263(6) Uani 1 1 d . . . . .
N7 N 0.4420(2) 0.1844(2) 0.32755(12) 0.0292(5) Uani 1 1 d . . . . .
C8 C 0.4543(3) 0.2839(3) 0.28921(14) 0.0252(6) Uani 1 1 d . . . . .
N9 N 0.5296(2) 0.2727(2) 0.21292(11) 0.0274(5) Uani 1 1 d . . . . .
C10 C 0.5196(3) 0.4035(3) 0.19664(14) 0.0273(6) Uani 1 1 d . . . . .
C11 C 0.4405(3) 0.4936(3) 0.25836(14) 0.0275(6) Uani 1 1 d . . . . .
H11 H 0.418866 0.587646 0.261762 0.033 Uiso 1 1 calc R U . . .
C12 C 0.3954(3) 0.4224(3) 0.31736(14) 0.0250(6) Uani 1 1 d . . . . .
C21 C 0.1633(3) 0.5017(3) 0.55120(14) 0.0273(6) Uani 1 1 d . . . . .
O22 O 0.1112(2) 0.6119(2) 0.52890(10) 0.0411(5) Uani 1 1 d . . . . .
O23 O 0.1771(2) 0.47149(19) 0.62035(9) 0.0314(4) Uani 1 1 d . . . . .
C24 C 0.1129(3) 0.5800(3) 0.68504(15) 0.0361(7) Uani 1 1 d . . . . .
C25 C 0.1917(4) 0.6720(3) 0.67272(19) 0.0517(9) Uani 1 1 d . . . . .
H25A H 0.299406 0.616559 0.657353 0.078 Uiso 1 1 calc R U . . .
H25B H 0.168057 0.728344 0.719771 0.078 Uiso 1 1 calc R U . . .
H25C H 0.158760 0.730884 0.633054 0.078 Uiso 1 1 calc R U . . .
C26 C 0.1520(4) 0.4953(4) 0.74984(17) 0.0520(9) Uani 1 1 d . . . . .
H26A H 0.108195 0.429810 0.753362 0.078 Uiso 1 1 calc R U . . .
H26B H 0.112834 0.554901 0.797041 0.078 Uiso 1 1 calc R U . . .
H26C H 0.260459 0.446200 0.741204 0.078 Uiso 1 1 calc R U . . .
C27 C -0.0539(4) 0.6553(4) 0.6943(2) 0.0614(10) Uani 1 1 d . . . . .
H27A H -0.074970 0.707078 0.650601 0.092 Uiso 1 1 calc R U . . .
H27B H -0.097010 0.717978 0.740444 0.092 Uiso 1 1 calc R U . . .
H27C H -0.097571 0.589746 0.697834 0.092 Uiso 1 1 calc R U . . .
C31 C 0.5482(3) 0.1741(3) 0.15585(14) 0.0305(6) Uani 1 1 d . . . . .
O32 O 0.5379(3) 0.2018(2) 0.09307(11) 0.0489(6) Uani 1 1 d . . . . .
O33 O 0.5793(2) 0.05592(19) 0.18285(10) 0.0381(5) Uani 1 1 d . . . . .
C34 C 0.5792(4) -0.0584(3) 0.13828(17) 0.0459(8) Uani 1 1 d . . . . .
C35 C 0.6128(7) -0.1685(4) 0.1913(2) 0.0943(18) Uani 1 1 d . . . . .
H35A H 0.617281 -0.251192 0.167336 0.141 Uiso 1 1 calc R U . . .
H35B H 0.534277 -0.138130 0.237962 0.141 Uiso 1 1 calc R U . . .
H35C H 0.708689 -0.187905 0.203229 0.141 Uiso 1 1 calc R U . . .
C36 C 0.4292(5) -0.0163(4) 0.1215(3) 0.0789(13) Uani 1 1 d . . . . .
H36A H 0.411896 0.056567 0.087669 0.118 Uiso 1 1 calc R U . . .
H36B H 0.352312 0.016654 0.168736 0.118 Uiso 1 1 calc R U . . .
H36C H 0.425189 -0.094552 0.097196 0.118 Uiso 1 1 calc R U . . .
C37 C 0.7035(5) -0.1006(4) 0.0676(2) 0.0746(12) Uani 1 1 d . . . . .
H37A H 0.708856 -0.180718 0.040316 0.112 Uiso 1 1 calc R U . . .
H37B H 0.798185 -0.122632 0.081542 0.112 Uiso 1 1 calc R U . . .
H37C H 0.683836 -0.025565 0.035109 0.112 Uiso 1 1 calc R U . . .
C41 C 0.1742(3) 0.2162(3) 0.59393(14) 0.0275(6) Uani 1 1 d . . . . .
C42 C 0.0241(3) 0.2885(3) 0.62628(16) 0.0346(7) Uani 1 1 d . . . . .
H42 H -0.034455 0.365108 0.603610 0.041 Uiso 1 1 calc R U . . .
C43 C -0.0411(3) 0.2502(3) 0.69121(17) 0.0399(7) Uani 1 1 d . . . . .
H43 H -0.143967 0.301098 0.713481 0.048 Uiso 1 1 calc R U . . .
C44 C 0.0426(3) 0.1380(3) 0.72398(16) 0.0368(7) Uani 1 1 d . . . . .
C45 C 0.1925(3) 0.0649(3) 0.69245(16) 0.0396(7) Uani 1 1 d . . . . .
H45 H 0.250377 -0.012282 0.714964 0.048 Uiso 1 1 calc R U . . .
C46 C 0.2581(3) 0.1048(3) 0.62775(16) 0.0361(7) Uani 1 1 d . . . . .
H46 H 0.361583 0.055287 0.606321 0.043 Uiso 1 1 calc R U . . .
C47 C -0.0289(4) 0.0940(4) 0.7934(2) 0.0542(9) Uani 1 1 d . . . . .
F471 F -0.1735(10) 0.1667(15) 0.8143(8) 0.094(5) Uani 0.5 1 d . . P A 1
F472 F 0.012(2) 0.121(3) 0.8539(4) 0.132(5) Uani 0.5 1 d . . P A 1
F473 F -0.016(3) -0.0225(11) 0.7881(11) 0.188(10) Uani 0.5 1 d . . P A 1
F474 F -0.124(3) 0.1854(11) 0.8409(9) 0.155(8) Uani 0.5 1 d . . P A 2
F475 F 0.0671(8) 0.0012(17) 0.8250(7) 0.101(3) Uani 0.5 1 d . . P A 2
F476 F -0.0948(19) 0.020(2) 0.7760(7) 0.125(7) Uani 0.5 1 d . . P A 2
C51 C 0.6023(3) 0.4268(3) 0.12532(14) 0.0287(6) Uani 1 1 d . . . . .
C52 C 0.7470(3) 0.3335(3) 0.09279(16) 0.0401(7) Uani 1 1 d . . . . .
H52 H 0.791443 0.251508 0.115258 0.048 Uiso 1 1 calc R U . . .
C53 C 0.8268(3) 0.3598(3) 0.02760(17) 0.0433(8) Uani 1 1 d . . . . .
H53 H 0.925706 0.295838 0.005527 0.052 Uiso 1 1 calc R U . . .
C54 C 0.7625(3) 0.4786(3) -0.00509(15) 0.0365(7) Uani 1 1 d . . . . .
C55 C 0.6185(3) 0.5719(3) 0.02667(15) 0.0353(7) Uani 1 1 d . . . . .
H55 H 0.574389 0.653503 0.003775 0.042 Uiso 1 1 calc R U . . .
C56 C 0.5386(3) 0.5464(3) 0.09186(15) 0.0311(6) Uani 1 1 d . . . . .
H56 H 0.439926 0.610968 0.113837 0.037 Uiso 1 1 calc R U . . .
C57 C 0.8471(4) 0.5060(4) -0.07607(17) 0.0470(8) Uani 1 1 d . . . . .
F571 F 0.7945(16) 0.5019(18) -0.1363(8) 0.077(4) Uani 0.5 1 d . . P B 1
F572 F 0.9884(17) 0.4154(19) -0.0961(12) 0.106(6) Uani 0.5 1 d . . P B 1
F573 F 0.848(2) 0.6240(15) -0.0709(10) 0.098(5) Uani 0.5 1 d . . P B 1
F574 F 0.816(2) 0.4713(19) -0.1357(8) 0.104(6) Uani 0.5 1 d . . P B 2
F575 F 0.9906(15) 0.438(2) -0.0851(12) 0.096(6) Uani 0.5 1 d . . P B 2
F576 F 0.8237(18) 0.6344(13) -0.0802(10) 0.097(5) Uani 0.5 1 d . . P B 2
C60 C 0.7088(6) 0.2248(6) 0.5596(3) 0.0866(16) Uani 1 1 d . . . . .
H60 H 0.748(5) 0.286(5) 0.564(3) 0.104 Uiso 1 1 d . U . . .
Cl61 Cl 0.7574(4) 0.1268(3) 0.47794(13) 0.0930(10) Uani 0.5 1 d . . P C 1
Cl62 Cl 0.5188(4) 0.3052(4) 0.5861(3) 0.1391(15) Uani 0.5 1 d . . P C 1
Cl63 Cl 0.7552(4) 0.1093(3) 0.63575(17) 0.0955(9) Uani 0.5 1 d . . P C 1
Cl64 Cl 0.8645(4) 0.0894(3) 0.4992(2) 0.1064(11) Uani 0.5 1 d . . P C 2
Cl65 Cl 0.5678(3) 0.3293(7) 0.50836(19) 0.219(3) Uani 0.5 1 d . . P C 2
Cl66 Cl 0.6187(6) 0.1941(5) 0.63676(18) 0.156(2) Uani 0.5 1 d . . P C 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
N1 C2 1.322(3) . ?
N1 C12 1.350(3) . ?
C2 N3 1.403(3) . ?
C2 C6 1.415(4) . ?
N3 C4 1.413(3) . ?
N3 C21 1.416(3) . ?
C4 C5 1.357(4) . ?
C4 C41 1.479(4) . ?
C5 C6 1.422(4) . ?
C5 H5 0.9500 . ?
C6 N7 1.352(3) . ?
N7 C8 1.318(3) . ?
C8 N9 1.414(3) . ?
C8 C12 1.417(4) . ?
N9 C10 1.414(3) . ?
N9 C31 1.422(3) . ?
C10 C11 1.355(4) . ?
C10 C51 1.471(4) . ?
C11 C12 1.427(4) . ?
C11 H11 0.9500 . ?
C21 O22 1.197(3) . ?
C21 O23 1.320(3) . ?
O23 C24 1.499(3) . ?
C24 C26 1.509(4) . ?
C24 C25 1.510(4) . ?
C24 C27 1.514(4) . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
C31 O32 1.194(3) . ?
C31 O33 1.307(3) . ?
O33 C34 1.488(3) . ?
C34 C36 1.497(5) . ?
C34 C35 1.504(5) . ?
C34 C37 1.514(5) . ?
C35 H35A 0.9800 . ?
C35 H35B 0.9800 . ?
C35 H35C 0.9800 . ?
C36 H36A 0.9800 . ?
C36 H36B 0.9800 . ?
C36 H36C 0.9800 . ?
C37 H37A 0.9800 . ?
C37 H37B 0.9800 . ?
C37 H37C 0.9800 . ?
C41 C42 1.383(4) . ?
C41 C46 1.387(4) . ?
C42 C43 1.378(4) . ?
C42 H42 0.9500 . ?
C43 C44 1.380(4) . ?
C43 H43 0.9500 . ?
C44 C45 1.380(4) . ?
C44 C47 1.498(4) . ?
C45 C46 1.385(4) . ?
C45 H45 0.9500 . ?
C46 H46 0.9500 . ?
C47 F473 1.217(9) . ?
C47 F474 1.232(10) . ?
C47 F475 1.308(7) . ?
C47 F471 1.313(10) . ?
C47 F476 1.320(11) . ?
C47 F472 1.334(8) . ?
C51 C52 1.390(4) . ?
C51 C56 1.390(4) . ?
C52 C53 1.387(4) . ?
C52 H52 0.9500 . ?
C53 C54 1.377(4) . ?
C53 H53 0.9500 . ?
C54 C55 1.382(4) . ?
C54 C57 1.494(4) . ?
C55 C56 1.384(4) . ?
C55 H55 0.9500 . ?
C56 H56 0.9500 . ?
C57 F573 1.290(13) . ?
C57 F574 1.293(13) . ?
C57 F575 1.303(15) . ?
C57 F576 1.316(13) . ?
C57 F571 1.328(14) . ?
C57 F572 1.328(16) . ?
C60 Cl66 1.619(5) . ?
C60 Cl61 1.689(5) . ?
C60 Cl62 1.710(6) . ?
C60 Cl64 1.791(6) . ?
C60 Cl65 1.847(7) . ?
C60 Cl63 1.865(6) . ?
C60 H60 0.92(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
C2 N1 C12 111.7(2) . . ?
N1 C2 N3 126.9(2) . . ?
N1 C2 C6 125.6(2) . . ?
N3 C2 C6 107.3(2) . . ?
C2 N3 C4 107.5(2) . . ?
C2 N3 C21 123.0(2) . . ?
C4 N3 C21 128.7(2) . . ?
C5 C4 N3 109.6(2) . . ?
C5 C4 C41 125.7(2) . . ?
N3 C4 C41 124.5(2) . . ?
C4 C5 C6 108.0(2) . . ?
C4 C5 H5 126.0 . . ?
C6 C5 H5 126.0 . . ?
N7 C6 C2 122.7(2) . . ?
N7 C6 C5 129.7(2) . . ?
C2 C6 C5 107.6(2) . . ?
C8 N7 C6 111.4(2) . . ?
N7 C8 N9 126.7(2) . . ?
N7 C8 C12 126.1(2) . . ?
N9 C8 C12 107.2(2) . . ?
C8 N9 C10 107.2(2) . . ?
C8 N9 C31 124.8(2) . . ?
C10 N9 C31 122.1(2) . . ?
C11 C10 N9 109.9(2) . . ?
C11 C10 C51 127.4(2) . . ?
N9 C10 C51 122.2(2) . . ?
C10 C11 C12 108.0(2) . . ?
C10 C11 H11 126.0 . . ?
C12 C11 H11 126.0 . . ?
N1 C12 C8 122.4(2) . . ?
N1 C12 C11 130.0(2) . . ?
C8 C12 C11 107.6(2) . . ?
O22 C21 O23 128.3(2) . . ?
O22 C21 N3 122.2(2) . . ?
O23 C21 N3 109.6(2) . . ?
C21 O23 C24 121.3(2) . . ?
O23 C24 C26 100.9(2) . . ?
O23 C24 C25 109.3(2) . . ?
C26 C24 C25 110.9(3) . . ?
O23 C24 C27 109.8(2) . . ?
C26 C24 C27 111.8(3) . . ?
C25 C24 C27 113.3(3) . . ?
C24 C25 H25A 109.5 . . ?
C24 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C24 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C24 C26 H26A 109.5 . . ?
C24 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C24 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C24 C27 H27A 109.5 . . ?
C24 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C24 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
O32 C31 O33 128.1(3) . . ?
O32 C31 N9 121.9(3) . . ?
O33 C31 N9 110.0(2) . . ?
C31 O33 C34 120.2(2) . . ?
O33 C34 C36 109.3(3) . . ?
O33 C34 C35 101.9(2) . . ?
C36 C34 C35 112.7(4) . . ?
O33 C34 C37 109.4(3) . . ?
C36 C34 C37 112.8(3) . . ?
C35 C34 C37 110.2(4) . . ?
C34 C35 H35A 109.5 . . ?
C34 C35 H35B 109.5 . . ?
H35A C35 H35B 109.5 . . ?
C34 C35 H35C 109.5 . . ?
H35A C35 H35C 109.5 . . ?
H35B C35 H35C 109.5 . . ?
C34 C36 H36A 109.5 . . ?
C34 C36 H36B 109.5 . . ?
H36A C36 H36B 109.5 . . ?
C34 C36 H36C 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?
C34 C37 H37A 109.5 . . ?
C34 C37 H37B 109.5 . . ?
H37A C37 H37B 109.5 . . ?
C34 C37 H37C 109.5 . . ?
H37A C37 H37C 109.5 . . ?
H37B C37 H37C 109.5 . . ?
C42 C41 C46 119.1(2) . . ?
C42 C41 C4 121.6(2) . . ?
C46 C41 C4 119.1(2) . . ?
C43 C42 C41 120.4(3) . . ?
C43 C42 H42 119.8 . . ?
C41 C42 H42 119.8 . . ?
C42 C43 C44 120.2(3) . . ?
C42 C43 H43 119.9 . . ?
C44 C43 H43 119.9 . . ?
C45 C44 C43 120.1(3) . . ?
C45 C44 C47 119.6(3) . . ?
C43 C44 C47 120.3(3) . . ?
C44 C45 C46 119.5(3) . . ?
C44 C45 H45 120.2 . . ?
C46 C45 H45 120.2 . . ?
C45 C46 C41 120.6(3) . . ?
C45 C46 H46 119.7 . . ?
C41 C46 H46 119.7 . . ?
F474 C47 F475 110.8(9) . . ?
F473 C47 F471 103.5(11) . . ?
F474 C47 F476 105.9(10) . . ?
F475 C47 F476 97.3(7) . . ?
F473 C47 F472 112.0(10) . . ?
F471 C47 F472 100.4(7) . . ?
F473 C47 C44 115.5(6) . . ?
F474 C47 C44 116.4(6) . . ?
F475 C47 C44 113.3(4) . . ?
F471 C47 C44 113.2(6) . . ?
F476 C47 C44 111.2(6) . . ?
F472 C47 C44 111.0(5) . . ?
C52 C51 C56 119.3(2) . . ?
C52 C51 C10 120.7(2) . . ?
C56 C51 C10 120.0(2) . . ?
C53 C52 C51 120.2(3) . . ?
C53 C52 H52 119.9 . . ?
C51 C52 H52 119.9 . . ?
C54 C53 C52 120.0(3) . . ?
C54 C53 H53 120.0 . . ?
C52 C53 H53 120.0 . . ?
C53 C54 C55 120.3(3) . . ?
C53 C54 C57 120.1(3) . . ?
C55 C54 C57 119.6(3) . . ?
C54 C55 C56 119.9(3) . . ?
C54 C55 H55 120.0 . . ?
C56 C55 H55 120.0 . . ?
C55 C56 C51 120.3(3) . . ?
C55 C56 H56 119.9 . . ?
C51 C56 H56 119.9 . . ?
F574 C57 F575 105.9(13) . . ?
F574 C57 F576 105.8(12) . . ?
F575 C57 F576 105.3(11) . . ?
F573 C57 F571 106.2(12) . . ?
F573 C57 F572 106.5(12) . . ?
F571 C57 F572 103.8(12) . . ?
F573 C57 C54 112.5(8) . . ?
F574 C57 C54 112.2(8) . . ?
F575 C57 C54 112.3(9) . . ?
F576 C57 C54 114.7(7) . . ?
F571 C57 C54 113.9(7) . . ?
F572 C57 C54 113.2(8) . . ?
Cl61 C60 Cl62 108.4(3) . . ?
Cl66 C60 Cl64 120.8(4) . . ?
Cl66 C60 Cl65 106.4(4) . . ?
Cl64 C60 Cl65 112.4(3) . . ?
Cl61 C60 Cl63 107.8(3) . . ?
Cl62 C60 Cl63 102.2(3) . . ?
Cl66 C60 H60 117(3) . . ?
Cl61 C60 H60 121(3) . . ?
Cl62 C60 H60 110(3) . . ?
Cl64 C60 H60 101(3) . . ?
Cl65 C60 H60 97(3) . . ?
Cl63 C60 H60 106(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C12 N1 C2 N3 178.6(2) . . . . ?
C12 N1 C2 C6 2.7(4) . . . . ?
N1 C2 N3 C4 -175.7(2) . . . . ?
C6 C2 N3 C4 0.9(3) . . . . ?
N1 C2 N3 C21 -4.9(4) . . . . ?
C6 C2 N3 C21 171.6(2) . . . . ?
C2 N3 C4 C5 -0.6(3) . . . . ?
C21 N3 C4 C5 -170.7(2) . . . . ?
C2 N3 C4 C41 -175.1(2) . . . . ?
C21 N3 C4 C41 14.8(4) . . . . ?
N3 C4 C5 C6 0.1(3) . . . . ?
C41 C4 C5 C6 174.6(2) . . . . ?
N1 C2 C6 N7 -3.7(4) . . . . ?
N3 C2 C6 N7 179.7(2) . . . . ?
N1 C2 C6 C5 175.8(2) . . . . ?
N3 C2 C6 C5 -0.8(3) . . . . ?
C4 C5 C6 N7 179.9(3) . . . . ?
C4 C5 C6 C2 0.4(3) . . . . ?
C2 C6 N7 C8 1.6(4) . . . . ?
C5 C6 N7 C8 -177.8(3) . . . . ?
C6 N7 C8 N9 -179.9(2) . . . . ?
C6 N7 C8 C12 0.9(4) . . . . ?
N7 C8 N9 C10 -177.4(2) . . . . ?
C12 C8 N9 C10 1.9(3) . . . . ?
N7 C8 N9 C31 29.3(4) . . . . ?
C12 C8 N9 C31 -151.4(2) . . . . ?
C8 N9 C10 C11 -0.9(3) . . . . ?
C31 N9 C10 C11 153.2(2) . . . . ?
C8 N9 C10 C51 171.8(2) . . . . ?
C31 N9 C10 C51 -34.1(4) . . . . ?
N9 C10 C11 C12 -0.4(3) . . . . ?
C51 C10 C11 C12 -172.6(3) . . . . ?
C2 N1 C12 C8 -0.2(3) . . . . ?
C2 N1 C12 C11 -178.8(3) . . . . ?
N7 C8 C12 N1 -1.7(4) . . . . ?
N9 C8 C12 N1 179.0(2) . . . . ?
N7 C8 C12 C11 177.2(2) . . . . ?
N9 C8 C12 C11 -2.1(3) . . . . ?
C10 C11 C12 N1 -179.6(3) . . . . ?
C10 C11 C12 C8 1.5(3) . . . . ?
C2 N3 C21 O22 33.9(4) . . . . ?
C4 N3 C21 O22 -157.4(3) . . . . ?
C2 N3 C21 O23 -144.9(2) . . . . ?
C4 N3 C21 O23 23.8(4) . . . . ?
O22 C21 O23 C24 5.6(4) . . . . ?
N3 C21 O23 C24 -175.7(2) . . . . ?
C21 O23 C24 C26 177.8(2) . . . . ?
C21 O23 C24 C25 -65.2(3) . . . . ?
C21 O23 C24 C27 59.7(3) . . . . ?
C8 N9 C31 O32 140.2(3) . . . . ?
C10 N9 C31 O32 -9.4(4) . . . . ?
C8 N9 C31 O33 -41.1(3) . . . . ?
C10 N9 C31 O33 169.3(2) . . . . ?
O32 C31 O33 C34 -11.5(5) . . . . ?
N9 C31 O33 C34 169.8(2) . . . . ?
C31 O33 C34 C36 -58.0(4) . . . . ?
C31 O33 C34 C35 -177.5(3) . . . . ?
C31 O33 C34 C37 65.9(4) . . . . ?
C5 C4 C41 C42 -126.5(3) . . . . ?
N3 C4 C41 C42 47.2(4) . . . . ?
C5 C4 C41 C46 48.4(4) . . . . ?
N3 C4 C41 C46 -137.9(3) . . . . ?
C46 C41 C42 C43 0.0(4) . . . . ?
C4 C41 C42 C43 174.9(3) . . . . ?
C41 C42 C43 C44 -0.9(5) . . . . ?
C42 C43 C44 C45 0.9(5) . . . . ?
C42 C43 C44 C47 -178.4(3) . . . . ?
C43 C44 C45 C46 -0.1(5) . . . . ?
C47 C44 C45 C46 179.2(3) . . . . ?
C44 C45 C46 C41 -0.8(5) . . . . ?
C42 C41 C46 C45 0.9(4) . . . . ?
C4 C41 C46 C45 -174.1(3) . . . . ?
C45 C44 C47 F473 -56(2) . . . . ?
C43 C44 C47 F473 123(2) . . . . ?
C45 C44 C47 F474 141.5(17) . . . . ?
C43 C44 C47 F474 -39.2(17) . . . . ?
C45 C44 C47 F475 11.4(11) . . . . ?
C43 C44 C47 F475 -169.4(10) . . . . ?
C45 C44 C47 F471 -175.5(9) . . . . ?
C43 C44 C47 F471 3.7(10) . . . . ?
C45 C44 C47 F476 -97.1(10) . . . . ?
C43 C44 C47 F476 82.2(10) . . . . ?
C45 C44 C47 F472 72.4(13) . . . . ?
C43 C44 C47 F472 -108.3(13) . . . . ?
C11 C10 C51 C52 132.5(3) . . . . ?
N9 C10 C51 C52 -38.8(4) . . . . ?
C11 C10 C51 C56 -44.1(4) . . . . ?
N9 C10 C51 C56 144.6(3) . . . . ?
C56 C51 C52 C53 0.0(4) . . . . ?
C10 C51 C52 C53 -176.7(3) . . . . ?
C51 C52 C53 C54 0.0(5) . . . . ?
C52 C53 C54 C55 -0.1(5) . . . . ?
C52 C53 C54 C57 -178.9(3) . . . . ?
C53 C54 C55 C56 0.4(4) . . . . ?
C57 C54 C55 C56 179.1(3) . . . . ?
C54 C55 C56 C51 -0.5(4) . . . . ?
C52 C51 C56 C55 0.3(4) . . . . ?
C10 C51 C56 C55 176.9(2) . . . . ?
C53 C54 C57 F573 -128.5(10) . . . . ?
C55 C54 C57 F573 52.7(10) . . . . ?
C53 C54 C57 F574 95.9(10) . . . . ?
C55 C54 C57 F574 -82.9(10) . . . . ?
C53 C54 C57 F575 -23.3(11) . . . . ?
C55 C54 C57 F575 157.9(11) . . . . ?
C53 C54 C57 F576 -143.4(10) . . . . ?
C55 C54 C57 F576 37.8(10) . . . . ?
C53 C54 C57 F571 110.6(9) . . . . ?
C55 C54 C57 F571 -68.2(9) . . . . ?
C53 C54 C57 F572 -7.7(12) . . . . ?
C55 C54 C57 F572 173.5(11) . . . . ?

_refine_diff_density_max         0.823
_refine_diff_density_min         -0.695
_refine_diff_density_rms         0.052



#==================================================================


