# Supplementary Information (SI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2025

####################################################################### 
# 
# 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_dan10575_Y2
_database_code_depnum_ccdc_archive 'CCDC 2427615'
loop_
_audit_author_name
_audit_author_address
'Constantin G. Daniliuc'
;Organisch Chemisches Institut University of Muenster
Germany
;
_audit_update_record             
;
2025-02-27 deposited with the CCDC.	2025-07-15 downloaded from the CCDC.
;

_audit_creation_method           'APEX4 v2022.10-1'
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C37 H28 N4 O4'
_chemical_formula_iupac          ?
_chemical_formula_weight         592.63

_chemical_melting_point          ?

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.3355(8)
_cell_length_b                   11.5289(12)
_cell_length_c                   14.8376(15)
_cell_angle_alpha                100.397(3)
_cell_angle_beta                 93.544(3)
_cell_angle_gamma                110.076(3)
_cell_volume                     1462.0(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2996
_cell_measurement_theta_min      2.3439
_cell_measurement_theta_max      24.9536
_cell_measurement_temperature    102.(2)

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow-orange
_exptl_crystal_size_max          0.159
_exptl_crystal_size_mid          0.154
_exptl_crystal_size_min          0.063
_exptl_crystal_density_diffrn    1.346
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             620

_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
Krause, L., Herbst-Irmer, R., Sheldrick, G. M., Stalke, D. (2015).
"Comparison of silver and molybdenum microfocus X-ray sources for
single-crystal structure determination"
J. Appl. Cryst. 48, 3-10. doi:10.1107/S1600576714022985
;
_exptl_absorpt_correction_T_min  0.69
_exptl_absorpt_correction_T_max  0.99

_exptl_special_details           
;
;

_diffrn_ambient_temperature      102.(2)

_diffrn_source                   'Mo ImS'
_diffrn_source_type              'micro focus tube'
_diffrn_source_power             0.05
_diffrn_source_current           1.0
_diffrn_source_voltage           50

_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'MX mirror'

_diffrn_measurement_device       'Bruker D8 Venture Photon III'
_diffrn_measurement_device_type  'single crystal diffractometer'
_diffrn_measurement_method       'phi/omega scans'

_diffrn_detector_area_resol_mean 7.3910

_diffrn_reflns_number            33236
_diffrn_reflns_av_R_equivalents  0.1211
_diffrn_reflns_av_unetI/netI     0.1053
_diffrn_reflns_theta_min         2.34
_diffrn_reflns_theta_max         25.03
_diffrn_reflns_theta_full        25.03
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17

_refine_special_details          
;

Reflections were merged by SHELXL according to the crystal
class for the calculation of statistics and refinement.

_reflns_Friedel_fraction is defined as the number of unique
Friedel pairs measured divided by the number that would be
possible theoretically, ignoring centric projections and
systematic absences.
;

_reflns_number_total             5166
_reflns_number_gt                3584
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0890
_refine_ls_R_factor_gt           0.0630
_refine_ls_wR_factor_gt          0.1617
_refine_ls_wR_factor_ref         0.1877
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_restrained_S_all      1.014
_refine_ls_number_reflns         5166
_refine_ls_number_parameters     410
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0927P)²+0.0983P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.305
_refine_diff_density_min         -0.335
_refine_ls_extinction_method     'SHELXL-2019/1 (Sheldrick 2019)'
_refine_ls_extinction_coef       0.011(3)

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'

_computing_data_collection       'Bruker APEX4 v2022.10-1 Photon III'
_computing_cell_refinement       'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_data_reduction        'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_structure_solution    'SHELXT 2019/1 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2018)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 1380)'
_computing_publication_material  'SHELXT 2011/1 (Sheldrick, 2018)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N N1 1.0253(2) 1.1548(2) 0.68617(15) 0.0397(6) Uani d . . . 1 . .
N N2 0.5395(2) 0.4767(2) 0.37628(16) 0.0383(5) Uani d . . . 1 . .
N N3 0.5825(2) 0.81905(19) 0.37346(14) 0.0320(5) Uani d . . . 1 . .
N N4 0.9687(2) 0.8279(2) 0.68645(13) 0.0303(5) Uani d . . . 1 . .
O O1 0.78098(19) 1.04568(16) 0.48848(12) 0.0356(4) Uani d . . . 1 . .
O O2 0.80913(18) 0.59928(16) 0.55368(11) 0.0324(4) Uani d . . . 1 . .
O O3 0.6420(2) 0.88807(17) 0.98581(12) 0.0389(5) Uani d . . . 1 . .
O O4 0.29260(19) 0.44841(16) 0.05556(12) 0.0361(4) Uani d . . . 1 . .
C C1 0.8718(3) 0.9349(2) 0.58100(16) 0.0295(5) Uani d . . . 1 . .
C C2 0.8822(3) 0.8241(2) 0.60235(17) 0.0297(5) Uani d . . . 1 . .
C C3 0.8000(3) 0.7112(2) 0.54136(16) 0.0296(6) Uani d . . . 1 . .
C C4 0.6973(3) 0.7049(2) 0.46462(16) 0.0290(5) Uani d . . . 1 . .
C C5 0.6834(3) 0.8158(2) 0.44545(16) 0.0291(5) Uani d . . . 1 . .
C C6 0.7765(3) 0.9308(2) 0.50394(17) 0.0305(6) Uani d . . . 1 . .
C C7 0.9582(3) 1.0571(2) 0.64001(17) 0.0327(6) Uani d . . . 1 . .
C C8 0.6074(3) 0.5795(2) 0.41311(17) 0.0297(5) Uani d . . . 1 . .
C C11 0.6586(3) 1.0457(2) 0.42993(17) 0.0307(6) Uani d . . . 1 . .
C C12 0.5597(3) 0.9343(2) 0.37212(16) 0.0300(6) Uani d . . . 1 . .
C C13 0.4424(3) 0.9427(2) 0.31381(17) 0.0324(6) Uani d . . . 1 . .
H H13 0.371277 0.868026 0.274328 0.039000 Uiso calc U . R 1 . .
C C14 0.4280(3) 1.0572(2) 0.31245(18) 0.0336(6) Uani d . . . 1 . .
H H14 0.348393 1.060597 0.271154 0.040000 Uiso calc U . R 1 . .
C C15 0.5281(3) 1.1678(2) 0.37053(17) 0.0347(6) Uani d . . . 1 . .
H H15 0.517863 1.246685 0.369320 0.042000 Uiso calc U . R 1 . .
C C16 0.6435(3) 1.1606(2) 0.43041(17) 0.0339(6) Uani d . . . 1 . .
H H16 0.712054 1.234756 0.471667 0.041000 Uiso calc U . R 1 . .
C C21 1.0148(3) 0.7196(2) 0.67997(17) 0.0311(6) Uani d . . . 1 . .
C C22 0.9331(3) 0.6082(2) 0.61606(17) 0.0312(6) Uani d . . . 1 . .
C C23 0.9698(3) 0.5011(2) 0.61086(17) 0.0322(6) Uani d . . . 1 . .
H H23 0.913605 0.426335 0.565862 0.039000 Uiso calc U . R 1 . .
C C24 1.0893(3) 0.5045(3) 0.67208(18) 0.0362(6) Uani d . . . 1 . .
H H24 1.113754 0.430773 0.670811 0.043000 Uiso calc U . R 1 . .
C C25 1.1740(3) 0.6159(3) 0.73578(18) 0.0380(6) Uani d . . . 1 . .
H H25 1.256801 0.617439 0.777144 0.046000 Uiso calc U . R 1 . .
C C26 1.1398(3) 0.7253(3) 0.74007(17) 0.0340(6) Uani d . . . 1 . .
C C27 1.2354(3) 0.8473(3) 0.80589(19) 0.0400(6) Uani d . . . 1 . .
H H27A 1.187170 0.855771 0.862303 0.060000 Uiso calc U . R 1 . .
H H27B 1.242511 0.918463 0.776644 0.060000 Uiso calc U . R 1 . .
H H27C 1.338897 0.847194 0.821607 0.060000 Uiso calc U . R 1 . .
C C31 0.8832(3) 0.8414(2) 0.76512(17) 0.0310(6) Uani d . . . 1 . .
C C32 0.7456(3) 0.7462(2) 0.76886(16) 0.0304(6) Uani d . . . 1 . .
H H32 0.708726 0.671845 0.721156 0.037000 Uiso calc U . R 1 . .
C C33 0.6610(3) 0.7579(2) 0.84115(17) 0.0318(6) Uani d . . . 1 . .
H H33 0.566288 0.692461 0.842692 0.038000 Uiso calc U . R 1 . .
C C34 0.7157(3) 0.8661(2) 0.91145(17) 0.0333(6) Uani d . . . 1 . .
C C35 0.8540(3) 0.9625(2) 0.90804(17) 0.0344(6) Uani d . . . 1 . .
H H35 0.890906 1.036860 0.955744 0.041000 Uiso calc U . R 1 . .
C C36 0.9381(3) 0.9501(2) 0.83515(17) 0.0332(6) Uani d . . . 1 . .
H H36 1.032573 1.015601 0.833144 0.040000 Uiso calc U . R 1 . .
C C37 0.4998(3) 0.7914(3) 0.99224(19) 0.0390(6) Uani d . . . 1 . .
H H37A 0.517708 0.713958 1.000584 0.047000 Uiso calc U . R 1 . .
H H37B 0.426918 0.770139 0.935130 0.047000 Uiso calc U . R 1 . .
C C38 0.4350(3) 0.8423(3) 1.0745(2) 0.0471(7) Uani d . . . 1 . .
H H38A 0.510596 0.867405 1.129933 0.071000 Uiso calc U . R 1 . .
H H38B 0.340412 0.776614 1.083170 0.071000 Uiso calc U . R 1 . .
H H38C 0.412082 0.915856 1.063753 0.071000 Uiso calc U . R 1 . .
C C41 0.5080(3) 0.7140(2) 0.29654(17) 0.0308(6) Uani d . . . 1 . .
C C42 0.3513(3) 0.6480(2) 0.28818(17) 0.0318(6) Uani d . . . 1 . .
H H42 0.295637 0.665248 0.337116 0.038000 Uiso calc U . R 1 . .
C C43 0.2743(3) 0.5567(2) 0.20913(17) 0.0322(6) Uani d . . . 1 . .
H H43 0.166376 0.512584 0.203496 0.039000 Uiso calc U . R 1 . .
C C44 0.3567(3) 0.5308(2) 0.13861(17) 0.0321(6) Uani d . . . 1 . .
C C45 0.5161(3) 0.5914(2) 0.14937(17) 0.0320(6) Uani d . . . 1 . .
H H45 0.573283 0.568590 0.103053 0.038000 Uiso calc U . R 1 . .
C C46 0.5912(3) 0.6842(2) 0.22684(17) 0.0314(6) Uani d . . . 1 . .
H H46 0.699206 0.727695 0.232746 0.038000 Uiso calc U . R 1 . .
C C47 0.1280(3) 0.3856(3) 0.03903(18) 0.0383(6) Uani d . . . 1 . .
H H47A 0.076826 0.448304 0.048629 0.046000 Uiso calc U . R 1 . .
H H47B 0.093851 0.327921 0.081900 0.046000 Uiso calc U . R 1 . .
C C48 0.0880(3) 0.3119(3) -0.0596(2) 0.0510(8) Uani d . . . 1 . .
H H48A 0.122529 0.370037 -0.101208 0.076000 Uiso calc U . R 1 . .
H H48B -0.023722 0.267748 -0.073585 0.076000 Uiso calc U . R 1 . .
H H48C 0.139075 0.250084 -0.068058 0.076000 Uiso calc U . R 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
N1 C7 . 1.146(3) ?
N2 C8 . 1.146(3) ?
N3 C5 . 1.394(3) ?
N3 C12 . 1.420(3) ?
N3 C41 . 1.441(3) ?
N4 C2 . 1.430(3) ?
N4 C21 . 1.443(3) ?
N4 C31 . 1.469(3) ?
O1 C6 . 1.371(3) ?
O1 C11 . 1.392(3) ?
O2 C3 . 1.366(3) ?
O2 C22 . 1.399(3) ?
O3 C34 . 1.367(3) ?
O3 C37 . 1.432(3) ?
O4 C44 . 1.369(3) ?
O4 C47 . 1.439(3) ?
C1 C6 . 1.388(3) ?
C1 C2 . 1.403(4) ?
C1 C7 . 1.445(3) ?
C2 C3 . 1.380(3) ?
C3 C4 . 1.417(3) ?
C4 C5 . 1.404(3) ?
C4 C8 . 1.438(3) ?
C5 C6 . 1.403(3) ?
C11 C16 . 1.377(3) ?
C11 C12 . 1.389(3) ?
C12 C13 . 1.393(3) ?
C13 C14 . 1.376(4) ?
C13 H13 . 0.950000 ?
C14 C15 . 1.389(4) ?
C14 H14 . 0.950000 ?
C15 C16 . 1.388(4) ?
C15 H15 . 0.950000 ?
C16 H16 . 0.950000 ?
C21 C22 . 1.388(3) ?
C21 C26 . 1.400(3) ?
C22 C23 . 1.381(4) ?
C23 C24 . 1.380(4) ?
C23 H23 . 0.950000 ?
C24 C25 . 1.393(4) ?
C24 H24 . 0.950000 ?
C25 C26 . 1.395(4) ?
C25 H25 . 0.950000 ?
C26 C27 . 1.505(4) ?
C27 H27A . 0.980000 ?
C27 H27B . 0.980000 ?
C27 H27C . 0.980000 ?
C31 C32 . 1.386(3) ?
C31 C36 . 1.392(3) ?
C32 C33 . 1.385(3) ?
C32 H32 . 0.950000 ?
C33 C34 . 1.390(4) ?
C33 H33 . 0.950000 ?
C34 C35 . 1.396(4) ?
C35 C36 . 1.390(4) ?
C35 H35 . 0.950000 ?
C36 H36 . 0.950000 ?
C37 C38 . 1.508(4) ?
C37 H37A . 0.990000 ?
C37 H37B . 0.990000 ?
C38 H38A . 0.980000 ?
C38 H38B . 0.980000 ?
C38 H38C . 0.980000 ?
C41 C42 . 1.384(3) ?
C41 C46 . 1.394(3) ?
C42 C43 . 1.390(3) ?
C42 H42 . 0.950000 ?
C43 C44 . 1.386(4) ?
C43 H43 . 0.950000 ?
C44 C45 . 1.395(3) ?
C45 C46 . 1.378(3) ?
C45 H45 . 0.950000 ?
C46 H46 . 0.950000 ?
C47 C48 . 1.505(4) ?
C47 H47A . 0.990000 ?
C47 H47B . 0.990000 ?
C48 H48A . 0.980000 ?
C48 H48B . 0.980000 ?
C48 H48C . 0.980000 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C5 N3 C12 . . 118.54(19) ?
C5 N3 C41 . . 123.5(2) ?
C12 N3 C41 . . 117.85(19) ?
C2 N4 C21 . . 111.81(19) ?
C2 N4 C31 . . 110.81(18) ?
C21 N4 C31 . . 111.73(19) ?
C6 O1 C11 . . 116.94(19) ?
C3 O2 C22 . . 116.04(19) ?
C34 O3 C37 . . 117.4(2) ?
C44 O4 C47 . . 118.17(19) ?
C6 C1 C2 . . 121.3(2) ?
C6 C1 C7 . . 117.9(2) ?
C2 C1 C7 . . 120.7(2) ?
C3 C2 C1 . . 117.5(2) ?
C3 C2 N4 . . 121.4(2) ?
C1 C2 N4 . . 121.0(2) ?
O2 C3 C2 . . 121.8(2) ?
O2 C3 C4 . . 116.5(2) ?
C2 C3 C4 . . 121.7(2) ?
C5 C4 C3 . . 120.4(2) ?
C5 C4 C8 . . 124.3(2) ?
C3 C4 C8 . . 115.3(2) ?
N3 C5 C6 . . 118.1(2) ?
N3 C5 C4 . . 124.6(2) ?
C6 C5 C4 . . 117.3(2) ?
O1 C6 C1 . . 115.8(2) ?
O1 C6 C5 . . 122.6(2) ?
C1 C6 C5 . . 121.5(2) ?
N1 C7 C1 . . 178.9(3) ?
N2 C8 C4 . . 175.7(3) ?
C16 C11 C12 . . 122.2(2) ?
C16 C11 O1 . . 117.2(2) ?
C12 C11 O1 . . 120.6(2) ?
C11 C12 C13 . . 117.2(2) ?
C11 C12 N3 . . 119.7(2) ?
C13 C12 N3 . . 123.1(2) ?
C14 C13 C12 . . 121.1(2) ?
C14 C13 H13 . . 119.500000 ?
C12 C13 H13 . . 119.500000 ?
C13 C14 C15 . . 121.0(2) ?
C13 C14 H14 . . 119.500000 ?
C15 C14 H14 . . 119.500000 ?
C16 C15 C14 . . 118.5(2) ?
C16 C15 H15 . . 120.700000 ?
C14 C15 H15 . . 120.700000 ?
C11 C16 C15 . . 119.9(2) ?
C11 C16 H16 . . 120.000000 ?
C15 C16 H16 . . 120.000000 ?
C22 C21 C26 . . 119.6(2) ?
C22 C21 N4 . . 120.4(2) ?
C26 C21 N4 . . 120.0(2) ?
C23 C22 C21 . . 121.9(2) ?
C23 C22 O2 . . 116.7(2) ?
C21 C22 O2 . . 121.4(2) ?
C24 C23 C22 . . 118.9(2) ?
C24 C23 H23 . . 120.500000 ?
C22 C23 H23 . . 120.500000 ?
C23 C24 C25 . . 120.0(2) ?
C23 C24 H24 . . 120.000000 ?
C25 C24 H24 . . 120.000000 ?
C24 C25 C26 . . 121.4(2) ?
C24 C25 H25 . . 119.300000 ?
C26 C25 H25 . . 119.300000 ?
C25 C26 C21 . . 118.2(2) ?
C25 C26 C27 . . 121.5(2) ?
C21 C26 C27 . . 120.3(2) ?
C26 C27 H27A . . 109.500000 ?
C26 C27 H27B . . 109.500000 ?
H27A C27 H27B . . 109.500000 ?
C26 C27 H27C . . 109.500000 ?
H27A C27 H27C . . 109.500000 ?
H27B C27 H27C . . 109.500000 ?
C32 C31 C36 . . 119.7(2) ?
C32 C31 N4 . . 119.8(2) ?
C36 C31 N4 . . 120.4(2) ?
C33 C32 C31 . . 120.9(2) ?
C33 C32 H32 . . 119.500000 ?
C31 C32 H32 . . 119.500000 ?
C32 C33 C34 . . 119.5(2) ?
C32 C33 H33 . . 120.200000 ?
C34 C33 H33 . . 120.200000 ?
O3 C34 C33 . . 124.6(2) ?
O3 C34 C35 . . 115.5(2) ?
C33 C34 C35 . . 119.8(2) ?
C36 C35 C34 . . 120.3(2) ?
C36 C35 H35 . . 119.900000 ?
C34 C35 H35 . . 119.900000 ?
C35 C36 C31 . . 119.7(2) ?
C35 C36 H36 . . 120.200000 ?
C31 C36 H36 . . 120.200000 ?
O3 C37 C38 . . 107.2(2) ?
O3 C37 H37A . . 110.300000 ?
C38 C37 H37A . . 110.300000 ?
O3 C37 H37B . . 110.300000 ?
C38 C37 H37B . . 110.300000 ?
H37A C37 H37B . . 108.500000 ?
C37 C38 H38A . . 109.500000 ?
C37 C38 H38B . . 109.500000 ?
H38A C38 H38B . . 109.500000 ?
C37 C38 H38C . . 109.500000 ?
H38A C38 H38C . . 109.500000 ?
H38B C38 H38C . . 109.500000 ?
C42 C41 C46 . . 119.6(2) ?
C42 C41 N3 . . 120.0(2) ?
C46 C41 N3 . . 120.2(2) ?
C41 C42 C43 . . 120.9(2) ?
C41 C42 H42 . . 119.600000 ?
C43 C42 H42 . . 119.600000 ?
C44 C43 C42 . . 119.2(2) ?
C44 C43 H43 . . 120.400000 ?
C42 C43 H43 . . 120.400000 ?
O4 C44 C43 . . 124.6(2) ?
O4 C44 C45 . . 115.4(2) ?
C43 C44 C45 . . 120.0(2) ?
C46 C45 C44 . . 120.3(2) ?
C46 C45 H45 . . 119.800000 ?
C44 C45 H45 . . 119.800000 ?
C45 C46 C41 . . 119.8(2) ?
C45 C46 H46 . . 120.100000 ?
C41 C46 H46 . . 120.100000 ?
O4 C47 C48 . . 107.0(2) ?
O4 C47 H47A . . 110.300000 ?
C48 C47 H47A . . 110.300000 ?
O4 C47 H47B . . 110.300000 ?
C48 C47 H47B . . 110.300000 ?
H47A C47 H47B . . 108.600000 ?
C47 C48 H48A . . 109.500000 ?
C47 C48 H48B . . 109.500000 ?
H48A C48 H48B . . 109.500000 ?
C47 C48 H48C . . 109.500000 ?
H48A C48 H48C . . 109.500000 ?
H48B C48 H48C . . 109.500000 ?

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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C6 C1 C2 C3 . . . . 3.2(3) ?
C7 C1 C2 C3 . . . . -178.1(2) ?
C6 C1 C2 N4 . . . . -173.8(2) ?
C7 C1 C2 N4 . . . . 4.9(3) ?
C21 N4 C2 C3 . . . . 25.5(3) ?
C31 N4 C2 C3 . . . . -99.8(3) ?
C21 N4 C2 C1 . . . . -157.6(2) ?
C31 N4 C2 C1 . . . . 77.0(3) ?
C22 O2 C3 C2 . . . . -15.9(3) ?
C22 O2 C3 C4 . . . . 166.4(2) ?
C1 C2 C3 O2 . . . . 176.5(2) ?
N4 C2 C3 O2 . . . . -6.5(3) ?
C1 C2 C3 C4 . . . . -5.9(3) ?
N4 C2 C3 C4 . . . . 171.1(2) ?
O2 C3 C4 C5 . . . . -178.5(2) ?
C2 C3 C4 C5 . . . . 3.8(4) ?
O2 C3 C4 C8 . . . . 4.2(3) ?
C2 C3 C4 C8 . . . . -173.5(2) ?
C12 N3 C5 C6 . . . . -10.6(3) ?
C41 N3 C5 C6 . . . . 164.9(2) ?
C12 N3 C5 C4 . . . . 168.5(2) ?
C41 N3 C5 C4 . . . . -16.0(4) ?
C3 C4 C5 N3 . . . . -178.0(2) ?
C8 C4 C5 N3 . . . . -1.0(4) ?
C3 C4 C5 C6 . . . . 1.1(3) ?
C8 C4 C5 C6 . . . . 178.2(2) ?
C11 O1 C6 C1 . . . . -161.9(2) ?
C11 O1 C6 C5 . . . . 18.9(3) ?
C2 C1 C6 O1 . . . . -177.5(2) ?
C7 C1 C6 O1 . . . . 3.7(3) ?
C2 C1 C6 C5 . . . . 1.7(4) ?
C7 C1 C6 C5 . . . . -177.1(2) ?
N3 C5 C6 O1 . . . . -5.5(3) ?
C4 C5 C6 O1 . . . . 175.3(2) ?
N3 C5 C6 C1 . . . . 175.4(2) ?
C4 C5 C6 C1 . . . . -3.8(3) ?
C6 O1 C11 C16 . . . . 165.6(2) ?
C6 O1 C11 C12 . . . . -16.2(3) ?
C16 C11 C12 C13 . . . . -0.2(4) ?
O1 C11 C12 C13 . . . . -178.3(2) ?
C16 C11 C12 N3 . . . . 178.9(2) ?
O1 C11 C12 N3 . . . . 0.7(3) ?
C5 N3 C12 C11 . . . . 12.9(3) ?
C41 N3 C12 C11 . . . . -162.8(2) ?
C5 N3 C12 C13 . . . . -168.1(2) ?
C41 N3 C12 C13 . . . . 16.1(3) ?
C11 C12 C13 C14 . . . . 1.4(4) ?
N3 C12 C13 C14 . . . . -177.6(2) ?
C12 C13 C14 C15 . . . . -1.3(4) ?
C13 C14 C15 C16 . . . . -0.1(4) ?
C12 C11 C16 C15 . . . . -1.2(4) ?
O1 C11 C16 C15 . . . . 177.0(2) ?
C14 C15 C16 C11 . . . . 1.3(4) ?
C2 N4 C21 C22 . . . . -23.5(3) ?
C31 N4 C21 C22 . . . . 101.4(3) ?
C2 N4 C21 C26 . . . . 158.3(2) ?
C31 N4 C21 C26 . . . . -76.9(3) ?
C26 C21 C22 C23 . . . . 1.2(4) ?
N4 C21 C22 C23 . . . . -177.0(2) ?
C26 C21 C22 O2 . . . . -178.9(2) ?
N4 C21 C22 O2 . . . . 2.9(4) ?
C3 O2 C22 C23 . . . . -162.5(2) ?
C3 O2 C22 C21 . . . . 17.5(3) ?
C21 C22 C23 C24 . . . . 1.2(4) ?
O2 C22 C23 C24 . . . . -178.8(2) ?
C22 C23 C24 C25 . . . . -2.1(4) ?
C23 C24 C25 C26 . . . . 0.7(4) ?
C24 C25 C26 C21 . . . . 1.6(4) ?
C24 C25 C26 C27 . . . . -177.3(2) ?
C22 C21 C26 C25 . . . . -2.6(4) ?
N4 C21 C26 C25 . . . . 175.7(2) ?
C22 C21 C26 C27 . . . . 176.4(2) ?
N4 C21 C26 C27 . . . . -5.4(4) ?
C2 N4 C31 C32 . . . . 64.2(3) ?
C21 N4 C31 C32 . . . . -61.2(3) ?
C2 N4 C31 C36 . . . . -114.7(2) ?
C21 N4 C31 C36 . . . . 119.9(2) ?
C36 C31 C32 C33 . . . . 0.4(4) ?
N4 C31 C32 C33 . . . . -178.5(2) ?
C31 C32 C33 C34 . . . . -0.6(4) ?
C37 O3 C34 C33 . . . . 1.2(3) ?
C37 O3 C34 C35 . . . . -179.8(2) ?
C32 C33 C34 O3 . . . . 179.8(2) ?
C32 C33 C34 C35 . . . . 0.8(4) ?
O3 C34 C35 C36 . . . . -179.8(2) ?
C33 C34 C35 C36 . . . . -0.6(4) ?
C34 C35 C36 C31 . . . . 0.4(4) ?
C32 C31 C36 C35 . . . . -0.3(4) ?
N4 C31 C36 C35 . . . . 178.6(2) ?
C34 O3 C37 C38 . . . . -175.1(2) ?
C5 N3 C41 C42 . . . . 109.8(3) ?
C12 N3 C41 C42 . . . . -74.7(3) ?
C5 N3 C41 C46 . . . . -74.8(3) ?
C12 N3 C41 C46 . . . . 100.7(3) ?
C46 C41 C42 C43 . . . . -3.3(4) ?
N3 C41 C42 C43 . . . . 172.1(2) ?
C41 C42 C43 C44 . . . . 0.9(4) ?
C47 O4 C44 C43 . . . . 1.2(4) ?
C47 O4 C44 C45 . . . . -178.2(2) ?
C42 C43 C44 O4 . . . . -176.1(2) ?
C42 C43 C44 C45 . . . . 3.2(4) ?
O4 C44 C45 C46 . . . . 174.4(2) ?
C43 C44 C45 C46 . . . . -5.0(4) ?
C44 C45 C46 C41 . . . . 2.6(4) ?
C42 C41 C46 C45 . . . . 1.5(4) ?
N3 C41 C46 C45 . . . . -173.9(2) ?
C44 O4 C47 C48 . . . . 174.4(2) ?

####################################################################### 
# 
# 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_dan10717_4c
_database_code_depnum_ccdc_archive 'CCDC 2427616'
loop_
_audit_author_name
_audit_author_address
'Constantin G. Daniliuc'
;Organisch Chemisches Institut University of Muenster
Germany
;
_audit_update_record             
;
2025-02-27 deposited with the CCDC.	2025-07-15 downloaded from the CCDC.
;

_audit_creation_method           'APEX5 v2023.9-2'
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H13 F2 N3 O2'
_chemical_formula_iupac          ?
_chemical_formula_weight         389.35

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
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                   30.5559(13)
_cell_length_b                   6.7574(3)
_cell_length_c                   21.5694(9)
_cell_angle_alpha                90
_cell_angle_beta                 124.734(2)
_cell_angle_gamma                90
_cell_volume                     3660.0(3)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    7966
_cell_measurement_theta_min      3.5202
_cell_measurement_theta_max      66.3161
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.140
_exptl_crystal_size_mid          0.046
_exptl_crystal_size_min          0.042
_exptl_crystal_density_diffrn    1.413
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1600

_exptl_absorpt_coefficient_mu    0.898
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
Krause, L., Herbst-Irmer, R., Sheldrick, G. M., Stalke, D. (2015).
"Comparison of silver and molybdenum microfocus X-ray sources for
single-crystal structure determination"
J. Appl. Cryst. 48, 3-10. doi:10.1107/S1600576714022985
;
_exptl_absorpt_correction_T_min  0.60
_exptl_absorpt_correction_T_max  0.96

_exptl_special_details           
;
;

_diffrn_ambient_temperature      100.(2)

_diffrn_source                   'Cu ImS'
_diffrn_source_type              'micro focus tube'
_diffrn_source_power             0.05
_diffrn_source_current           1.0
_diffrn_source_voltage           50

_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_monochromator  'MX mirror'

_diffrn_measurement_device       'Bruker D8 Venture Photon III'
_diffrn_measurement_device_type  'single crystal diffractometer'
_diffrn_measurement_method       'phi/omega scans'

_diffrn_detector_area_resol_mean 7.3910

_diffrn_reflns_number            27987
_diffrn_reflns_av_R_equivalents  0.0818
_diffrn_reflns_av_unetI/netI     0.0464
_diffrn_reflns_theta_min         4.16
_diffrn_reflns_theta_max         66.75
_diffrn_reflns_theta_full        66.75
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_limit_h_min       -35
_diffrn_reflns_limit_h_max       36
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25

_refine_special_details          
;

Reflections were merged by SHELXL according to the crystal
class for the calculation of statistics and refinement.

_reflns_Friedel_fraction is defined as the number of unique
Friedel pairs measured divided by the number that would be
possible theoretically, ignoring centric projections and
systematic absences.
;

_reflns_number_total             3217
_reflns_number_gt                2507
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0619
_refine_ls_R_factor_gt           0.0480
_refine_ls_wR_factor_gt          0.1237
_refine_ls_wR_factor_ref         0.1368
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_restrained_S_all      1.020
_refine_ls_number_reflns         3217
_refine_ls_number_parameters     263
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0860P)²+1.3064P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.216
_refine_diff_density_min         -0.377
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'
F F 0.0727 0.0534 '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'

_computing_data_collection       'Bruker APEX4 v2021.4-0 Photon III'
_computing_cell_refinement       'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_data_reduction        'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 1242)'
_computing_publication_material  'SHELXT 2018/2 (Sheldrick, 2018)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F F1 0.14703(4) 0.50335(16) 0.19508(6) 0.0349(3) Uani d . . . 1 . .
F F2 0.07614(4) 0.54602(18) 0.23154(6) 0.0388(3) Uani d . . . 1 . .
O O1 0.21383(5) 0.52123(18) 0.48947(7) 0.0259(3) Uani d . . . 1 . .
O O2 0.45008(5) 0.42684(19) 0.40736(8) 0.0319(3) Uani d . . . 1 . .
N N1 0.07903(6) 0.5491(3) 0.39769(10) 0.0377(4) Uani d . . . 1 . .
N N2 0.27025(7) 0.4180(3) 0.26314(9) 0.0365(4) Uani d . . . 1 . .
N N3 0.29147(6) 0.4817(2) 0.45881(8) 0.0247(3) Uani d . . . 1 . .
C C1 0.21894(7) 0.4885(2) 0.32320(10) 0.0234(4) Uani d . . . 1 . .
C C2 0.16412(7) 0.5090(2) 0.26751(10) 0.0257(4) Uani d . . . 1 . .
C C3 0.12839(7) 0.5298(3) 0.28555(10) 0.0275(4) Uani d . . . 1 . .
C C4 0.14616(7) 0.5311(2) 0.36127(10) 0.0239(4) Uani d . . . 1 . .
C C5 0.20035(7) 0.5158(2) 0.41718(10) 0.0216(4) Uani d . . . 1 . .
C C6 0.23814(7) 0.4954(2) 0.39980(10) 0.0211(4) Uani d . . . 1 . .
C C7 0.10897(7) 0.5436(3) 0.38140(10) 0.0278(4) Uani d . . . 1 . .
C C8 0.25050(7) 0.4521(3) 0.29412(10) 0.0267(4) Uani d . . . 1 . .
C C11 0.35919(7) 0.4660(2) 0.59539(10) 0.0236(4) Uani d . . . 1 . .
H H11 0.386576 0.453341 0.587376 0.028000 Uiso calc U . R 1 . .
C C12 0.30632(7) 0.4821(2) 0.53386(10) 0.0208(4) Uani d . . . 1 . .
C C13 0.26746(7) 0.5006(2) 0.54826(10) 0.0210(4) Uani d . . . 1 . .
C C14 0.27992(7) 0.5034(2) 0.62042(10) 0.0215(4) Uani d . . . 1 . .
H H14 0.252522 0.516509 0.628407 0.026000 Uiso calc U . R 1 . .
C C15 0.33291(7) 0.4868(2) 0.68180(10) 0.0241(4) Uani d . . . 1 . .
H H15 0.342079 0.488145 0.731929 0.029000 Uiso calc U . R 1 . .
C C16 0.37204(7) 0.4682(3) 0.66823(10) 0.0258(4) Uani d . . . 1 . .
H H16 0.408275 0.456915 0.709644 0.031000 Uiso calc U . R 1 . .
C C21 0.33287(7) 0.4719(3) 0.44601(10) 0.0232(4) Uani d . . . 1 . .
C C22 0.35079(7) 0.6438(3) 0.43263(10) 0.0259(4) Uani d . . . 1 . .
H H22 0.336099 0.767851 0.432454 0.031000 Uiso calc U . R 1 . .
C C23 0.39034(7) 0.6351(3) 0.41941(10) 0.0266(4) Uani d . . . 1 . .
H H23 0.402395 0.752627 0.409435 0.032000 Uiso calc U . R 1 . .
C C24 0.41200(7) 0.4529(3) 0.42095(10) 0.0253(4) Uani d . . . 1 . .
C C25 0.39554(6) 0.2815(3) 0.43795(9) 0.0261(4) Uani d . . . 1 . .
H H25 0.411579 0.158045 0.441102 0.031000 Uiso calc U . R 1 . .
C C26 0.35595(6) 0.2910(3) 0.45019(9) 0.0251(4) Uani d . . . 1 . .
H H26 0.344493 0.174080 0.461449 0.030000 Uiso calc U . R 1 . .
C C27 0.46744(7) 0.5974(3) 0.38743(11) 0.0325(4) Uani d . . . 1 . .
H H27A 0.484959 0.693100 0.429708 0.039000 Uiso calc U . R 1 . .
H H27B 0.436692 0.663463 0.342679 0.039000 Uiso calc U . R 1 . .
C C28 0.50629(8) 0.5258(4) 0.37025(12) 0.0415(5) Uani d . . . 1 . .
H H28A 0.536762 0.462635 0.415202 0.062000 Uiso calc U . R 1 . .
H H28B 0.518698 0.638393 0.355559 0.062000 Uiso calc U . R 1 . .
H H28C 0.488601 0.429783 0.328840 0.062000 Uiso calc U . R 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
F1 C2 . 1.336(2) ?
F2 C3 . 1.341(2) ?
O1 C5 . 1.368(2) ?
O1 C13 . 1.395(2) ?
O2 C24 . 1.364(2) ?
O2 C27 . 1.433(2) ?
N1 C7 . 1.152(2) ?
N2 C8 . 1.150(2) ?
N3 C6 . 1.386(2) ?
N3 C12 . 1.411(2) ?
N3 C21 . 1.442(2) ?
C1 C6 . 1.404(3) ?
C1 C2 . 1.406(3) ?
C1 C8 . 1.440(2) ?
C2 C3 . 1.359(3) ?
C3 C4 . 1.397(3) ?
C4 C5 . 1.390(2) ?
C4 C7 . 1.432(2) ?
C5 C6 . 1.409(2) ?
C11 C16 . 1.385(3) ?
C11 C12 . 1.393(2) ?
C11 H11 . 0.950000 ?
C12 C13 . 1.394(2) ?
C13 C14 . 1.376(2) ?
C14 C15 . 1.394(2) ?
C14 H14 . 0.950000 ?
C15 C16 . 1.389(3) ?
C15 H15 . 0.950000 ?
C16 H16 . 0.950000 ?
C21 C22 . 1.383(2) ?
C21 C26 . 1.388(2) ?
C22 C23 . 1.392(2) ?
C22 H22 . 0.950000 ?
C23 C24 . 1.389(2) ?
C23 H23 . 0.950000 ?
C24 C25 . 1.393(2) ?
C25 C26 . 1.379(2) ?
C25 H25 . 0.950000 ?
C26 H26 . 0.950000 ?
C27 C28 . 1.511(3) ?
C27 H27A . 0.990000 ?
C27 H27B . 0.990000 ?
C28 H28A . 0.980000 ?
C28 H28B . 0.980000 ?
C28 H28C . 0.980000 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C5 O1 C13 . . 117.93(13) ?
C24 O2 C27 . . 117.86(14) ?
C6 N3 C12 . . 119.66(14) ?
C6 N3 C21 . . 121.88(15) ?
C12 N3 C21 . . 118.45(14) ?
C6 C1 C2 . . 119.85(16) ?
C6 C1 C8 . . 125.72(16) ?
C2 C1 C8 . . 114.37(16) ?
F1 C2 C3 . . 119.69(16) ?
F1 C2 C1 . . 118.53(16) ?
C3 C2 C1 . . 121.76(17) ?
F2 C3 C2 . . 120.83(17) ?
F2 C3 C4 . . 119.51(16) ?
C2 C3 C4 . . 119.65(16) ?
C5 C4 C3 . . 119.43(16) ?
C5 C4 C7 . . 120.03(16) ?
C3 C4 C7 . . 120.52(15) ?
O1 C5 C4 . . 115.04(15) ?
O1 C5 C6 . . 123.08(16) ?
C4 C5 C6 . . 121.88(17) ?
N3 C6 C1 . . 124.25(16) ?
N3 C6 C5 . . 118.37(16) ?
C1 C6 C5 . . 117.38(16) ?
N1 C7 C4 . . 178.44(19) ?
N2 C8 C1 . . 172.1(2) ?
C16 C11 C12 . . 120.35(15) ?
C16 C11 H11 . . 119.800000 ?
C12 C11 H11 . . 119.800000 ?
C11 C12 C13 . . 117.88(16) ?
C11 C12 N3 . . 122.23(15) ?
C13 C12 N3 . . 119.89(16) ?
C14 C13 C12 . . 122.12(16) ?
C14 C13 O1 . . 116.85(15) ?
C12 C13 O1 . . 121.02(16) ?
C13 C14 C15 . . 119.74(15) ?
C13 C14 H14 . . 120.100000 ?
C15 C14 H14 . . 120.100000 ?
C16 C15 C14 . . 118.72(16) ?
C16 C15 H15 . . 120.600000 ?
C14 C15 H15 . . 120.600000 ?
C11 C16 C15 . . 121.19(16) ?
C11 C16 H16 . . 119.400000 ?
C15 C16 H16 . . 119.400000 ?
C22 C21 C26 . . 120.42(15) ?
C22 C21 N3 . . 119.76(15) ?
C26 C21 N3 . . 119.77(15) ?
C21 C22 C23 . . 120.05(16) ?
C21 C22 H22 . . 120.000000 ?
C23 C22 H22 . . 120.000000 ?
C24 C23 C22 . . 119.31(16) ?
C24 C23 H23 . . 120.300000 ?
C22 C23 H23 . . 120.300000 ?
O2 C24 C23 . . 124.23(16) ?
O2 C24 C25 . . 115.43(15) ?
C23 C24 C25 . . 120.34(15) ?
C26 C25 C24 . . 119.96(16) ?
C26 C25 H25 . . 120.000000 ?
C24 C25 H25 . . 120.000000 ?
C25 C26 C21 . . 119.82(16) ?
C25 C26 H26 . . 120.100000 ?
C21 C26 H26 . . 120.100000 ?
O2 C27 C28 . . 107.01(16) ?
O2 C27 H27A . . 110.300000 ?
C28 C27 H27A . . 110.300000 ?
O2 C27 H27B . . 110.300000 ?
C28 C27 H27B . . 110.300000 ?
H27A C27 H27B . . 108.600000 ?
C27 C28 H28A . . 109.500000 ?
C27 C28 H28B . . 109.500000 ?
H28A C28 H28B . . 109.500000 ?
C27 C28 H28C . . 109.500000 ?
H28A C28 H28C . . 109.500000 ?
H28B C28 H28C . . 109.500000 ?

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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C6 C1 C2 F1 . . . . 179.49(14) ?
C8 C1 C2 F1 . . . . -3.2(2) ?
C6 C1 C2 C3 . . . . -2.0(2) ?
C8 C1 C2 C3 . . . . 175.24(16) ?
F1 C2 C3 F2 . . . . -0.4(2) ?
C1 C2 C3 F2 . . . . -178.90(15) ?
F1 C2 C3 C4 . . . . 178.49(14) ?
C1 C2 C3 C4 . . . . 0.0(3) ?
F2 C3 C4 C5 . . . . -179.51(14) ?
C2 C3 C4 C5 . . . . 1.5(2) ?
F2 C3 C4 C7 . . . . 1.8(2) ?
C2 C3 C4 C7 . . . . -177.12(16) ?
C13 O1 C5 C4 . . . . 178.10(13) ?
C13 O1 C5 C6 . . . . -1.6(2) ?
C3 C4 C5 O1 . . . . 179.10(14) ?
C7 C4 C5 O1 . . . . -2.2(2) ?
C3 C4 C5 C6 . . . . -1.2(2) ?
C7 C4 C5 C6 . . . . 177.51(15) ?
C12 N3 C6 C1 . . . . -177.39(15) ?
C21 N3 C6 C1 . . . . 4.2(2) ?
C12 N3 C6 C5 . . . . 2.0(2) ?
C21 N3 C6 C5 . . . . -176.41(15) ?
C2 C1 C6 N3 . . . . -178.30(15) ?
C8 C1 C6 N3 . . . . 4.8(3) ?
C2 C1 C6 C5 . . . . 2.3(2) ?
C8 C1 C6 C5 . . . . -174.59(15) ?
O1 C5 C6 N3 . . . . -0.5(2) ?
C4 C5 C6 N3 . . . . 179.81(15) ?
O1 C5 C6 C1 . . . . 178.93(14) ?
C4 C5 C6 C1 . . . . -0.8(2) ?
C16 C11 C12 C13 . . . . 0.1(2) ?
C16 C11 C12 N3 . . . . 179.61(15) ?
C6 N3 C12 C11 . . . . 179.09(15) ?
C21 N3 C12 C11 . . . . -2.5(2) ?
C6 N3 C12 C13 . . . . -1.4(2) ?
C21 N3 C12 C13 . . . . 177.07(14) ?
C11 C12 C13 C14 . . . . 0.1(2) ?
N3 C12 C13 C14 . . . . -179.49(14) ?
C11 C12 C13 O1 . . . . 178.76(14) ?
N3 C12 C13 O1 . . . . -0.8(2) ?
C5 O1 C13 C14 . . . . -178.99(14) ?
C5 O1 C13 C12 . . . . 2.3(2) ?
C12 C13 C14 C15 . . . . -0.2(2) ?
O1 C13 C14 C15 . . . . -178.92(14) ?
C13 C14 C15 C16 . . . . 0.2(2) ?
C12 C11 C16 C15 . . . . -0.1(3) ?
C14 C15 C16 C11 . . . . 0.0(2) ?
C6 N3 C21 C22 . . . . 81.3(2) ?
C12 N3 C21 C22 . . . . -97.12(19) ?
C6 N3 C21 C26 . . . . -101.29(19) ?
C12 N3 C21 C26 . . . . 80.3(2) ?
C26 C21 C22 C23 . . . . 3.3(3) ?
N3 C21 C22 C23 . . . . -179.30(15) ?
C21 C22 C23 C24 . . . . -1.0(3) ?
C27 O2 C24 C23 . . . . -2.4(2) ?
C27 O2 C24 C25 . . . . 178.23(15) ?
C22 C23 C24 O2 . . . . 178.65(16) ?
C22 C23 C24 C25 . . . . -2.1(3) ?
O2 C24 C25 C26 . . . . -177.89(15) ?
C23 C24 C25 C26 . . . . 2.8(3) ?
C24 C25 C26 C21 . . . . -0.4(3) ?
C22 C21 C26 C25 . . . . -2.6(3) ?
N3 C21 C26 C25 . . . . 179.99(15) ?
C24 O2 C27 C28 . . . . -176.09(15) ?


####################################################################### 
# 
# 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_alh_fr18m

_database_code_depnum_ccdc_archive 'CCDC 2429053'
loop_
_audit_author_name
_audit_author_address
'Christoph Wolper'
;Universitaet Duisburg Essen
Germany
;
_audit_update_record             
;
2025-03-05 deposited with the CCDC.	2025-07-15 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT097_alh_fr18m           
;
PROBLEM: Large Reported Max.  (Positive) Residual Density       0.91 eA-3  
RESPONSE: Likely Fourier truncation effect. Peak lies close to a bond centre. 
Also possibly part of a non-refineable rocking motion disorder. see below.
;
_vrf_PLAT230_alh_fr18m           
;
PROBLEM: Hirshfeld Test Diff for    C14      --C15      .        8.9 s.u.  
RESPONSE: The orientation of the displacement ellipsoids show a rocking 
motion that cannot be refined as disorder.
;
# end Validation Reply Form
_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C34 H22 N4 O2'
_chemical_formula_weight         518.55

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

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

_shelx_space_group_comment       
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;

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

_cell_length_a                   6.8945(7)
_cell_length_b                   7.9423(8)
_cell_length_c                   12.3462(12)
_cell_angle_alpha                74.095(3)
_cell_angle_beta                 83.457(3)
_cell_angle_gamma                82.201(3)
_cell_volume                     642.07(11)
_cell_formula_units_Z            1
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9935
_cell_measurement_theta_min      2.68
_cell_measurement_theta_max      33.19

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.341
_exptl_crystal_F_000             270
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.302
_exptl_crystal_size_mid          0.188
_exptl_crystal_size_min          0.074
_exptl_absorpt_coefficient_mu    0.085
_shelx_estimated_absorpt_T_min   0.975
_shelx_estimated_absorpt_T_max   0.994
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.70
_exptl_absorpt_correction_T_max  0.75
_exptl_absorpt_process_details   'SADABS, Blessing, Acta Cryst 1995 A51 33-38'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_radiation_monochromator  'Triumph Goebel mirror'
_diffrn_measurement_device_type  'Bruker D8 KAPPA II (APEX II detector)'
_diffrn_measurement_method       'Data collection strategy APEX 3/Queen'
_diffrn_detector_area_resol_mean 512
_diffrn_reflns_number            52443
_diffrn_reflns_av_unetI/netI     0.0195
_diffrn_reflns_av_R_equivalents  0.0374
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.683
_diffrn_reflns_theta_max         33.265
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4924
_reflns_number_gt                4009
_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 APEX3(v2019.1-0)'
_computing_cell_refinement       'BRUKER APEX3(v2019.1-0)'
_computing_data_reduction        'BRUKER APEX3(v2019.1-0)'
_computing_structure_solution    'BRUKER APEX3(v2019.1-0)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'ORTEP/PLATON (Spek)'
_computing_publication_material  'BRUKER AXS SHELXTL (c) 2008 / Vers. 2008/4'
_refine_special_details          
;
 Treatment of hydrogen atoms:    
 Riding model on idealized geometries 
 with the 1.2 fold isotropic displacement 
 parameters of the equivalent Uij of the 
 corresponding carbon atom.
 The methyl groups are idealized with
 tetrahedral angles in a combined 
 rotating and rigid group refinement
 with the 1.5 fold isotropic displacement
 parameters of the equivalent Uij of the 
 corresponding carbon atom.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0812P)²+0.2416P] 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     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4924
_refine_ls_number_parameters     183
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0610
_refine_ls_R_factor_gt           0.0478
_refine_ls_wR_factor_ref         0.1438
_refine_ls_wR_factor_gt          0.1329
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_restrained_S_all      1.041
_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 1.21640(10) 1.22857(10) 0.55236(6) 0.01402(15) Uani 1 1 d . . . . .
N1 N 0.48339(13) 0.88294(13) 0.65856(8) 0.01913(18) Uani 1 1 d . . . . .
N2 N 0.85576(11) 1.15129(10) 0.68043(7) 0.01108(15) Uani 1 1 d . . . . .
C1 C 0.82045(13) 0.96246(12) 0.55776(7) 0.01063(16) Uani 1 1 d . . . . .
C2 C 0.92619(13) 1.07803(12) 0.58897(7) 0.01017(15) Uani 1 1 d . . . . .
C3 C 1.10518(13) 1.11574(12) 0.52897(8) 0.01091(16) Uani 1 1 d . . . . .
C4 C 0.63339(14) 0.91993(12) 0.61437(8) 0.01285(17) Uani 1 1 d . . . . .
C5 C 1.12283(14) 1.33999(12) 0.61553(8) 0.01283(17) Uani 1 1 d . . . . .
C6 C 0.94252(13) 1.30821(12) 0.67644(8) 0.01230(17) Uani 1 1 d . . . . .
C7 C 0.84920(14) 1.42960(13) 0.73443(8) 0.01372(17) Uani 1 1 d . . . . .
C8 C 0.94733(15) 1.57124(13) 0.73554(9) 0.01591(18) Uani 1 1 d . . . . .
H8 H 0.887143 1.652110 0.776766 0.019 Uiso 1 1 calc R U . . .
C9 C 1.13104(15) 1.59776(13) 0.67799(9) 0.01689(19) Uani 1 1 d . . . . .
H9 H 1.196376 1.693645 0.681782 0.020 Uiso 1 1 calc R U . . .
C10 C 1.21801(15) 1.48312(13) 0.61504(9) 0.01599(18) Uani 1 1 d . . . . .
H10 H 1.340456 1.502387 0.572437 0.019 Uiso 1 1 calc R U . . .
C11 C 0.64930(15) 1.40908(14) 0.79527(9) 0.01851(19) Uani 1 1 d . . . . .
H11A H 0.661382 1.324429 0.869336 0.028 Uiso 1 1 calc R U . . .
H11B H 0.567449 1.366169 0.750851 0.028 Uiso 1 1 calc R U . . .
H11C H 0.588401 1.523216 0.805375 0.028 Uiso 1 1 calc R U . . .
C12 C 0.86958(14) 1.02043(13) 0.79014(8) 0.01356(17) Uani 1 1 d . . . . .
C13 C 0.69971(16) 0.97140(15) 0.85639(9) 0.0188(2) Uani 1 1 d . . . . .
H13 H 0.574435 1.024418 0.832355 0.023 Uiso 1 1 calc R U . . .
C14 C 0.71549(19) 0.84369(16) 0.95834(9) 0.0237(2) Uani 1 1 d . . . . .
H14 H 0.599672 0.808628 1.003776 0.028 Uiso 1 1 calc R U . . .
C15 C 0.8975(2) 0.76632(17) 0.99506(10) 0.0298(3) Uani 1 1 d . . . . .
H15 H 0.906361 0.680079 1.065447 0.036 Uiso 1 1 calc R U . . .
C16 C 1.0669(2) 0.81625(16) 0.92785(10) 0.0264(2) Uani 1 1 d . . . . .
H16 H 1.192034 0.762798 0.951816 0.032 Uiso 1 1 calc R U . . .
C17 C 1.05337(16) 0.94390(14) 0.82590(9) 0.01818(19) Uani 1 1 d . . . . .
H17 H 1.169193 0.979116 0.780531 0.022 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 C3 1.3613(11) . ?
O1 C5 1.3843(11) . ?
N1 C4 1.1487(13) . ?
N2 C2 1.4171(11) . ?
N2 C6 1.4406(12) . ?
N2 C12 1.4680(12) . ?
C1 C3 1.3959(12) 2_776 ?
C1 C2 1.4007(12) . ?
C1 C4 1.4315(12) . ?
C2 C3 1.3898(12) . ?
C5 C10 1.3859(14) . ?
C5 C6 1.3939(13) . ?
C6 C7 1.4004(13) . ?
C7 C8 1.3930(14) . ?
C7 C11 1.4994(14) . ?
C8 C9 1.3924(14) . ?
C9 C10 1.3878(14) . ?
C12 C13 1.3868(14) . ?
C12 C17 1.3933(14) . ?
C13 C14 1.3880(16) . ?
C14 C15 1.388(2) . ?
C15 C16 1.390(2) . ?
C16 C17 1.3865(16) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 O1 C5 116.66(7) . . ?
C2 N2 C6 113.12(7) . . ?
C2 N2 C12 112.20(7) . . ?
C6 N2 C12 112.37(7) . . ?
C3 C1 C2 121.03(8) 2_776 . ?
C3 C1 C4 117.94(8) 2_776 . ?
C2 C1 C4 121.02(8) . . ?
C3 C2 C1 117.89(8) . . ?
C3 C2 N2 120.83(8) . . ?
C1 C2 N2 121.27(8) . . ?
O1 C3 C2 121.90(8) . . ?
O1 C3 C1 117.03(8) . 2_776 ?
C2 C3 C1 121.06(8) . 2_776 ?
N1 C4 C1 178.48(10) . . ?
O1 C5 C10 116.55(8) . . ?
O1 C5 C6 121.24(8) . . ?
C10 C5 C6 122.21(9) . . ?
C5 C6 C7 119.02(8) . . ?
C5 C6 N2 120.12(8) . . ?
C7 C6 N2 120.86(8) . . ?
C8 C7 C6 118.41(9) . . ?
C8 C7 C11 120.00(9) . . ?
C6 C7 C11 121.60(9) . . ?
C9 C8 C7 121.93(9) . . ?
C10 C9 C8 119.52(9) . . ?
C5 C10 C9 118.73(9) . . ?
C13 C12 C17 120.50(10) . . ?
C13 C12 N2 119.80(9) . . ?
C17 C12 N2 119.68(9) . . ?
C12 C13 C14 118.99(11) . . ?
C15 C14 C13 121.15(11) . . ?
C14 C15 C16 119.36(11) . . ?
C17 C16 C15 120.13(12) . . ?
C16 C17 C12 119.86(11) . . ?

_refine_diff_density_max         0.910
_refine_diff_density_min         -0.248
_refine_diff_density_rms         0.066

####################################################################### 
# 
# 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_alh_206_5dm

_database_code_depnum_ccdc_archive 'CCDC 2429052'
loop_
_audit_author_name
_audit_author_address
'Christoph Wolper'
;Universitaet Duisburg Essen
Germany
;
_audit_update_record             
;
2025-03-05 deposited with the CCDC.	2025-07-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C36 H26 N4 O4'
_chemical_formula_weight         578.61

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      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                   7.6840(7)
_cell_length_b                   7.9687(8)
_cell_length_c                   12.3504(12)
_cell_angle_alpha                71.581(3)
_cell_angle_beta                 72.351(3)
_cell_angle_gamma                85.723(3)
_cell_volume                     683.53(12)
_cell_formula_units_Z            1
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9882
_cell_measurement_theta_min      3.95
_cell_measurement_theta_max      80.33

_exptl_crystal_description       plate
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.406
_exptl_crystal_F_000             302
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.306
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.048
_exptl_absorpt_coefficient_mu    0.755
_shelx_estimated_absorpt_T_min   0.802
_shelx_estimated_absorpt_T_max   0.965
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.59
_exptl_absorpt_correction_T_max  0.75
_exptl_absorpt_process_details   'SADABS, Blessing, Acta Cryst 1995 A51 33-38'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro-focus sealed tube'
_diffrn_source_type              'INCOATEC I\mS 3.0'
_diffrn_radiation_monochromator  'multilayer mirror'
_diffrn_measurement_device_type  'Bruker D8 Venture (Photon II detector)'
_diffrn_measurement_method       'Data collection strategy APEX 3/Queen'
_diffrn_detector_area_resol_mean 7.3910
_diffrn_reflns_number            32614
_diffrn_reflns_av_unetI/netI     0.0191
_diffrn_reflns_av_R_equivalents  0.0408
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.949
_diffrn_reflns_theta_max         80.549
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2975
_reflns_number_gt                2716
_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 APEX3(v2017.3-0)'
_computing_cell_refinement       'Bruker APEX3(v2017.3-0)'
_computing_data_reduction        'Bruker APEX3(v2017.3-0)'
_computing_structure_solution    'Bruker APEX3(v2017.3-0)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'ORTEP/PLATON (Spek)'
_computing_publication_material  'BRUKER AXS SHELXTL (c) 2008 / Vers. 2008/4'
_refine_special_details          
;
 Treatment of hydrogen atoms:    
 Riding model on idealized geometries 
 with the 1.2 fold isotropic displacement 
 parameters of the equivalent Uij of the 
 corresponding carbon atom.
 The methyl groups are idealized with
 tetrahedral angles in a combined 
 rotating and rigid group refinement
 with the 1.5 fold isotropic displacement
 parameters of the equivalent Uij of the 
 corresponding carbon atom.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0482P)²+0.2220P] 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     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2975
_refine_ls_number_parameters     200
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0378
_refine_ls_R_factor_gt           0.0345
_refine_ls_wR_factor_ref         0.0964
_refine_ls_wR_factor_gt          0.0928
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_restrained_S_all      1.067
_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 0.18613(10) 0.70663(9) 0.96185(6) 0.01786(17) Uani 1 1 d . . . . .
O2 O -0.54994(10) 1.15503(10) 0.57410(6) 0.02064(18) Uani 1 1 d . . . . .
N1 N -0.38385(14) 1.24927(13) 0.86043(9) 0.0269(2) Uani 1 1 d . . . . .
N2 N -0.08058(12) 0.84138(12) 0.84402(8) 0.0184(2) Uani 1 1 d . . . . .
C1 C -0.13309(13) 1.07344(13) 0.94502(8) 0.0154(2) Uani 1 1 d . . . . .
C2 C -0.04293(13) 0.92335(13) 0.91934(9) 0.0154(2) Uani 1 1 d . . . . .
C3 C 0.08900(13) 0.85356(13) 0.97678(9) 0.0150(2) Uani 1 1 d . . . . .
C4 C -0.27239(14) 1.16514(13) 0.89439(9) 0.0185(2) Uani 1 1 d . . . . .
C5 C 0.15130(13) 0.62737(13) 0.88490(8) 0.0158(2) Uani 1 1 d . . . . .
C6 C 0.01876(13) 0.69111(13) 0.82672(9) 0.0161(2) Uani 1 1 d . . . . .
C7 C -0.01147(14) 0.60060(13) 0.75395(9) 0.0184(2) Uani 1 1 d . . . . .
H7 H -0.102762 0.639470 0.714662 0.022 Uiso 1 1 calc R U . . .
C8 C 0.09110(14) 0.45347(13) 0.73827(9) 0.0195(2) Uani 1 1 d . . . . .
H8 H 0.068594 0.392534 0.688830 0.023 Uiso 1 1 calc R U . . .
C9 C 0.22592(14) 0.39545(13) 0.79445(9) 0.0193(2) Uani 1 1 d . . . . .
H9 H 0.297423 0.296768 0.782367 0.023 Uiso 1 1 calc R U . . .
C10 C 0.25514(13) 0.48403(13) 0.86903(9) 0.0171(2) Uani 1 1 d . . . . .
H10 H 0.346253 0.445362 0.908500 0.021 Uiso 1 1 calc R U . . .
C11 C -0.19677(14) 0.92062(13) 0.77053(9) 0.0167(2) Uani 1 1 d . . . . .
C12 C -0.38182(14) 0.87300(13) 0.81136(9) 0.0184(2) Uani 1 1 d . . . . .
H12 H -0.430135 0.784941 0.885996 0.022 Uiso 1 1 calc R U . . .
C13 C -0.49422(14) 0.95478(13) 0.74253(9) 0.0185(2) Uani 1 1 d . . . . .
H13 H -0.620697 0.923935 0.770728 0.022 Uiso 1 1 calc R U . . .
C14 C -0.42392(14) 1.08247(13) 0.63179(9) 0.0173(2) Uani 1 1 d . . . . .
C15 C -0.23721(14) 1.12518(13) 0.58851(9) 0.0187(2) Uani 1 1 d . . . . .
H15 H -0.187592 1.208906 0.512132 0.022 Uiso 1 1 calc R U . . .
C16 C -0.12468(14) 1.04315(13) 0.65905(9) 0.0187(2) Uani 1 1 d . . . . .
H16 H 0.002401 1.071442 0.630493 0.022 Uiso 1 1 calc R U . . .
C17 C -0.48747(14) 1.28639(14) 0.45926(9) 0.0197(2) Uani 1 1 d . . . . .
H17A H -0.402782 1.233938 0.401082 0.024 Uiso 1 1 calc R U . . .
H17B H -0.422641 1.384673 0.464903 0.024 Uiso 1 1 calc R U . . .
C18 C -0.65498(15) 1.35307(14) 0.42041(10) 0.0223(2) Uani 1 1 d . . . . .
H18A H -0.618275 1.442233 0.341467 0.033 Uiso 1 1 calc R U . . .
H18B H -0.736651 1.406079 0.478161 0.033 Uiso 1 1 calc R U . . .
H18C H -0.718713 1.254164 0.416404 0.033 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 C3 1.3728(12) . ?
O1 C5 1.3901(12) . ?
O2 C14 1.3617(12) . ?
O2 C17 1.4359(12) . ?
N1 C4 1.1461(14) . ?
N2 C2 1.3968(13) . ?
N2 C6 1.4102(13) . ?
N2 C11 1.4369(12) . ?
C1 C3 1.4030(13) 2_577 ?
C1 C2 1.4121(14) . ?
C1 C4 1.4391(13) . ?
C2 C3 1.3940(14) . ?
C5 C10 1.3750(14) . ?
C5 C6 1.3956(14) . ?
C6 C7 1.3939(14) . ?
C7 C8 1.3951(14) . ?
C8 C9 1.3893(15) . ?
C9 C10 1.3990(14) . ?
C11 C16 1.3873(14) . ?
C11 C12 1.3946(14) . ?
C12 C13 1.3800(14) . ?
C13 C14 1.3973(14) . ?
C14 C15 1.3974(14) . ?
C15 C16 1.3951(14) . ?
C17 C18 1.5102(14) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 O1 C5 117.85(8) . . ?
C14 O2 C17 117.87(8) . . ?
C2 N2 C6 118.78(8) . . ?
C2 N2 C11 121.65(8) . . ?
C6 N2 C11 118.91(8) . . ?
C3 C1 C2 121.01(9) 2_577 . ?
C3 C1 C4 114.55(9) 2_577 . ?
C2 C1 C4 124.44(9) . . ?
C3 C2 N2 119.49(9) . . ?
C3 C2 C1 115.98(9) . . ?
N2 C2 C1 124.51(9) . . ?
O1 C3 C2 122.61(9) . . ?
O1 C3 C1 114.38(9) . 2_577 ?
C2 C3 C1 123.01(9) . 2_577 ?
N1 C4 C1 173.26(11) . . ?
C10 C5 O1 116.32(9) . . ?
C10 C5 C6 122.13(9) . . ?
O1 C5 C6 121.56(9) . . ?
C7 C6 C5 117.88(9) . . ?
C7 C6 N2 122.42(9) . . ?
C5 C6 N2 119.70(9) . . ?
C6 C7 C8 120.62(9) . . ?
C9 C8 C7 120.47(9) . . ?
C8 C9 C10 119.22(9) . . ?
C5 C10 C9 119.65(9) . . ?
C16 C11 C12 120.19(9) . . ?
C16 C11 N2 120.05(9) . . ?
C12 C11 N2 119.76(9) . . ?
C13 C12 C11 119.50(9) . . ?
C12 C13 C14 120.68(9) . . ?
O2 C14 C13 114.71(9) . . ?
O2 C14 C15 125.38(9) . . ?
C13 C14 C15 119.91(9) . . ?
C16 C15 C14 119.07(9) . . ?
C11 C16 C15 120.57(9) . . ?
O2 C17 C18 106.73(8) . . ?

_refine_diff_density_max         0.254
_refine_diff_density_min         -0.247
_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_dan10606_4d
_database_code_depnum_ccdc_archive 'CCDC 2427617'
loop_
_audit_author_name
_audit_author_address
'Constantin G. Daniliuc'
;Organisch Chemisches Institut University of Muenster
Germany
;
_audit_update_record             
;
2025-02-27 deposited with the CCDC.	2025-07-15 downloaded from the CCDC.
;

_audit_creation_method           'APEX4 v2022.10-1'
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H15 F2 N3 O2'
_chemical_formula_iupac          ?
_chemical_formula_weight         403.38

_chemical_melting_point          ?

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   11.6575(2)
_cell_length_b                   12.9957(3)
_cell_length_c                   14.0878(3)
_cell_angle_alpha                66.3220(10)
_cell_angle_beta                 89.8080(10)
_cell_angle_gamma                75.4290(10)
_cell_volume                     1880.21(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9889
_cell_measurement_theta_min      3.9420
_cell_measurement_theta_max      66.6968
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.166
_exptl_crystal_size_mid          0.074
_exptl_crystal_size_min          0.039
_exptl_crystal_density_diffrn    1.425
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             832

_exptl_absorpt_coefficient_mu    0.894
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
Krause, L., Herbst-Irmer, R., Sheldrick, G. M., Stalke, D. (2015).
"Comparison of silver and molybdenum microfocus X-ray sources for
single-crystal structure determination"
J. Appl. Cryst. 48, 3-10. doi:10.1107/S1600576714022985
;
_exptl_absorpt_correction_T_min  0.84
_exptl_absorpt_correction_T_max  0.97

_exptl_special_details           
;
;

_diffrn_ambient_temperature      100.(2)

_diffrn_source                   'Cu ImS'
_diffrn_source_type              'micro focus tube'
_diffrn_source_power             0.05
_diffrn_source_current           1.0
_diffrn_source_voltage           50

_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_monochromator  'MX mirror'

_diffrn_measurement_device       'Bruker D8 Venture Photon III'
_diffrn_measurement_device_type  'single crystal diffractometer'
_diffrn_measurement_method       'phi/omega scans'

_diffrn_detector_area_resol_mean 7.3910

_diffrn_reflns_number            30628
_diffrn_reflns_av_R_equivalents  0.0392
_diffrn_reflns_av_unetI/netI     0.0299
_diffrn_reflns_theta_min         3.86
_diffrn_reflns_theta_max         66.73
_diffrn_reflns_theta_full        66.73
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16

_refine_special_details          
;

Reflections were merged by SHELXL according to the crystal
class for the calculation of statistics and refinement.

_reflns_Friedel_fraction is defined as the number of unique
Friedel pairs measured divided by the number that would be
possible theoretically, ignoring centric projections and
systematic absences.
;

_reflns_number_total             6609
_reflns_number_gt                5636
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0417
_refine_ls_R_factor_gt           0.0337
_refine_ls_wR_factor_gt          0.0829
_refine_ls_wR_factor_ref         0.0883
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_restrained_S_all      1.031
_refine_ls_number_reflns         6609
_refine_ls_number_parameters     545
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0428P)²+0.6758P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.209
_refine_diff_density_min         -0.196
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'
F F 0.0727 0.0534 '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'

_computing_data_collection       'Bruker APEX4 v2022.10-1 Photon III'
_computing_cell_refinement       'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_data_reduction        'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_structure_solution    'SHELXT 2019/1 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2018)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 1380)'
_computing_publication_material  'SHELXT 2011/1 (Sheldrick, 2018)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F F1A 0.69998(7) 0.73600(7) 0.59315(6) 0.02397(19) Uani d . . . 1 . .
F F2A 0.53139(7) 0.68032(7) 0.72083(6) 0.02551(19) Uani d . . . 1 . .
N N1A 0.21661(12) 0.75488(12) 0.70462(10) 0.0316(3) Uani d . . . 1 . .
N N2A 0.71543(11) 0.94149(12) 0.33852(11) 0.0305(3) Uani d . . . 1 . .
N N3A 0.39808(10) 1.00992(10) 0.31221(9) 0.0174(2) Uani d . . . 1 . .
O O1A 0.22978(8) 0.96218(8) 0.45710(7) 0.0190(2) Uani d . . . 1 . .
O O2A 0.43571(9) 0.77730(9) 0.04764(8) 0.0241(2) Uani d . . . 1 . .
C C1A 0.55368(12) 0.87851(12) 0.45734(11) 0.0177(3) Uani d . . . 1 . .
C C2A 0.58552(12) 0.79350(12) 0.55932(11) 0.0187(3) Uani d . . . 1 . .
C C3A 0.49975(13) 0.76491(12) 0.62453(11) 0.0196(3) Uani d . . . 1 . .
C C4A 0.37960(12) 0.82179(12) 0.58988(11) 0.0186(3) Uani d . . . 1 . .
C C5A 0.34778(12) 0.90716(12) 0.48754(11) 0.0173(3) Uani d . . . 1 . .
C C6A 0.43304(12) 0.93283(12) 0.41893(10) 0.0168(3) Uani d . . . 1 . .
C C7A 0.28897(13) 0.78665(13) 0.65470(11) 0.0216(3) Uani d . . . 1 . .
C C8A 0.64464(12) 0.91085(13) 0.39141(11) 0.0210(3) Uani d . . . 1 . .
C C11A 0.25554(13) 1.20235(13) 0.20987(11) 0.0207(3) Uani d . . . 1 . .
C C12A 0.28502(12) 1.09482(12) 0.29682(11) 0.0179(3) Uani d . . . 1 . .
C C13A 0.20488(12) 1.07091(12) 0.37095(11) 0.0180(3) Uani d . . . 1 . .
C C14A 0.09778(12) 1.15072(13) 0.36394(11) 0.0204(3) Uani d . . . 1 . .
H H14A 0.045201 1.133021 0.416196 0.025000 Uiso calc U . R 1 . .
C C15A 0.06970(13) 1.25768(13) 0.27785(12) 0.0229(3) Uani d . . . 1 . .
H H15A -0.003160 1.314417 0.270952 0.027000 Uiso calc U . R 1 . .
C C16A 0.14679(13) 1.28239(13) 0.20206(11) 0.0226(3) Uani d . . . 1 . .
H H16A 0.125161 1.355612 0.143292 0.027000 Uiso calc U . R 1 . .
C C17A 0.33829(14) 1.23010(14) 0.12626(12) 0.0269(3) Uani d . . . 1 . .
H H17A 0.325974 1.195795 0.077900 0.040000 Uiso calc U . R 1 . .
H H17B 0.421112 1.197542 0.158481 0.040000 Uiso calc U . R 1 . .
H H17C 0.321552 1.314996 0.088075 0.040000 Uiso calc U . R 1 . .
C C21A 0.40793(12) 0.94746(12) 0.24418(10) 0.0172(3) Uani d . . . 1 . .
C C22A 0.32518(12) 0.88780(13) 0.24357(11) 0.0198(3) Uani d . . . 1 . .
H H22A 0.263398 0.886771 0.287809 0.024000 Uiso calc U . R 1 . .
C C23A 0.33110(13) 0.82937(13) 0.17921(11) 0.0212(3) Uani d . . . 1 . .
H H23A 0.273368 0.789302 0.178861 0.025000 Uiso calc U . R 1 . .
C C24A 0.42226(12) 0.83009(12) 0.11535(11) 0.0189(3) Uani d . . . 1 . .
C C25A 0.50771(13) 0.88774(13) 0.11787(11) 0.0212(3) Uani d . . . 1 . .
H H25A 0.571750 0.885859 0.076165 0.025000 Uiso calc U . R 1 . .
C C26A 0.49956(12) 0.94764(12) 0.18085(11) 0.0203(3) Uani d . . . 1 . .
H H26A 0.556466 0.988714 0.180739 0.024000 Uiso calc U . R 1 . .
C C27A 0.34156(13) 0.72985(14) 0.03318(12) 0.0260(3) Uani d . . . 1 . .
H H27A 0.263367 0.788466 0.018791 0.031000 Uiso calc U . R 1 . .
H H27B 0.340526 0.659967 0.096805 0.031000 Uiso calc U . R 1 . .
C C28A 0.36508(15) 0.69758(17) -0.05778(14) 0.0357(4) Uani d . . . 1 . .
H H28A 0.362847 0.767895 -0.120793 0.054000 Uiso calc U . R 1 . .
H H28B 0.303892 0.662244 -0.068139 0.054000 Uiso calc U . R 1 . .
H H28C 0.443818 0.641591 -0.043630 0.054000 Uiso calc U . R 1 . .
F F1B 0.40634(7) 0.49834(7) 0.85813(6) 0.02357(19) Uani d . . . 1 . .
F F2B 0.53455(7) 0.45121(7) 0.71355(6) 0.02342(19) Uani d . . . 1 . .
N N1B 0.50911(11) 0.36075(11) 0.51967(10) 0.0263(3) Uani d . . . 1 . .
N N2B 0.13270(11) 0.51521(11) 0.93786(10) 0.0244(3) Uani d . . . 1 . .
N N3B 0.07973(10) 0.38848(10) 0.75255(9) 0.0166(2) Uani d . . . 1 . .
O O1B 0.22221(8) 0.34058(8) 0.60289(7) 0.0181(2) Uani d . . . 1 . .
O O2B 0.05141(9) 0.02549(9) 1.13244(8) 0.0236(2) Uani d . . . 1 . .
C C1B 0.24362(12) 0.44949(11) 0.80405(10) 0.0170(3) Uani d . . . 1 . .
C C2B 0.35907(12) 0.46190(12) 0.79492(11) 0.0185(3) Uani d . . . 1 . .
C C3B 0.42402(12) 0.43844(12) 0.72154(11) 0.0183(3) Uani d . . . 1 . .
C C4B 0.37618(12) 0.40023(12) 0.65520(11) 0.0171(3) Uani d . . . 1 . .
C C5B 0.26205(12) 0.38374(11) 0.66609(10) 0.0160(3) Uani d . . . 1 . .
C C6B 0.19405(12) 0.40770(11) 0.74060(10) 0.0162(3) Uani d . . . 1 . .
C C7B 0.44783(12) 0.37686(12) 0.57913(11) 0.0189(3) Uani d . . . 1 . .
C C8B 0.17894(12) 0.48358(12) 0.87860(11) 0.0188(3) Uani d . . . 1 . .
C C11B -0.09568(12) 0.39832(12) 0.64830(11) 0.0199(3) Uani d . . . 1 . .
C C12B 0.02782(12) 0.37907(12) 0.66464(10) 0.0173(3) Uani d . . . 1 . .
C C13B 0.09932(12) 0.35155(12) 0.59435(11) 0.0172(3) Uani d . . . 1 . .
C C14B 0.05482(13) 0.33422(12) 0.51300(11) 0.0197(3) Uani d . . . 1 . .
H H14B 0.105947 0.315018 0.466408 0.024000 Uiso calc U . R 1 . .
C C15B -0.06658(13) 0.34553(12) 0.50088(11) 0.0214(3) Uani d . . . 1 . .
H H15B -0.098951 0.330646 0.447425 0.026000 Uiso calc U . R 1 . .
C C16B -0.14038(12) 0.37861(12) 0.56703(11) 0.0216(3) Uani d . . . 1 . .
H H16B -0.223564 0.388132 0.556841 0.026000 Uiso calc U . R 1 . .
C C17B -0.17927(13) 0.44304(13) 0.71321(12) 0.0249(3) Uani d . . . 1 . .
H H17D -0.179976 0.378263 0.779950 0.037000 Uiso calc U . R 1 . .
H H17E -0.259854 0.477495 0.676064 0.037000 Uiso calc U . R 1 . .
H H17F -0.152458 0.502506 0.725949 0.037000 Uiso calc U . R 1 . .
C C21B 0.07207(12) 0.29584(12) 0.85326(10) 0.0173(3) Uani d . . . 1 . .
C C22B 0.00231(12) 0.32204(12) 0.92454(11) 0.0194(3) Uani d . . . 1 . .
H H22B -0.039041 0.400902 0.908991 0.023000 Uiso calc U . R 1 . .
C C23B -0.00772(12) 0.23372(12) 1.01883(11) 0.0200(3) Uani d . . . 1 . .
H H23B -0.056563 0.252106 1.067070 0.024000 Uiso calc U . R 1 . .
C C24B 0.05403(12) 0.11849(12) 1.04212(11) 0.0193(3) Uani d . . . 1 . .
C C25B 0.12566(13) 0.09233(13) 0.97057(11) 0.0222(3) Uani d . . . 1 . .
H H25B 0.168722 0.013791 0.986609 0.027000 Uiso calc U . R 1 . .
C C26B 0.13398(12) 0.18034(12) 0.87665(11) 0.0196(3) Uani d . . . 1 . .
H H26B 0.182012 0.162100 0.827912 0.024000 Uiso calc U . R 1 . .
C C27B -0.03147(13) 0.04546(13) 1.20323(11) 0.0230(3) Uani d . . . 1 . .
H H27C -0.114362 0.065652 1.171868 0.028000 Uiso calc U . R 1 . .
H H27D -0.021733 0.110882 1.218662 0.028000 Uiso calc U . R 1 . .
C C28B -0.00585(13) -0.06489(14) 1.30154(11) 0.0257(3) Uani d . . . 1 . .
H H28D -0.010957 -0.129950 1.284751 0.039000 Uiso calc U . R 1 . .
H H28E -0.064365 -0.055549 1.349631 0.039000 Uiso calc U . R 1 . .
H H28F 0.074485 -0.081166 1.334372 0.039000 Uiso calc U . R 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
F1A C2A . 1.3351(16) ?
F2A C3A . 1.3366(16) ?
N1A C7A . 1.147(2) ?
N2A C8A . 1.1479(19) ?
N3A C6A . 1.4209(18) ?
N3A C12A . 1.4422(18) ?
N3A C21A . 1.4723(17) ?
O1A C5A . 1.3603(16) ?
O1A C13A . 1.4045(17) ?
O2A C24A . 1.3696(17) ?
O2A C27A . 1.4385(17) ?
C1A C2A . 1.395(2) ?
C1A C6A . 1.4028(19) ?
C1A C8A . 1.438(2) ?
C2A C3A . 1.374(2) ?
C3A C4A . 1.393(2) ?
C4A C5A . 1.400(2) ?
C4A C7A . 1.435(2) ?
C5A C6A . 1.3909(19) ?
C11A C16A . 1.395(2) ?
C11A C12A . 1.399(2) ?
C11A C17A . 1.508(2) ?
C12A C13A . 1.392(2) ?
C13A C14A . 1.382(2) ?
C14A C15A . 1.389(2) ?
C14A H14A . 0.950000 ?
C15A C16A . 1.383(2) ?
C15A H15A . 0.950000 ?
C16A H16A . 0.950000 ?
C17A H17A . 0.980000 ?
C17A H17B . 0.980000 ?
C17A H17C . 0.980000 ?
C21A C22A . 1.383(2) ?
C21A C26A . 1.3893(19) ?
C22A C23A . 1.389(2) ?
C22A H22A . 0.950000 ?
C23A C24A . 1.389(2) ?
C23A H23A . 0.950000 ?
C24A C25A . 1.397(2) ?
C25A C26A . 1.385(2) ?
C25A H25A . 0.950000 ?
C26A H26A . 0.950000 ?
C27A C28A . 1.505(2) ?
C27A H27A . 0.990000 ?
C27A H27B . 0.990000 ?
C28A H28A . 0.980000 ?
C28A H28B . 0.980000 ?
C28A H28C . 0.980000 ?
F1B C2B . 1.3395(15) ?
F2B C3B . 1.3388(15) ?
N1B C7B . 1.1478(18) ?
N2B C8B . 1.1478(19) ?
N3B C6B . 1.4139(17) ?
N3B C12B . 1.4417(17) ?
N3B C21B . 1.4669(17) ?
O1B C5B . 1.3631(16) ?
O1B C13B . 1.4042(16) ?
O2B C24B . 1.3653(17) ?
O2B C27B . 1.4389(17) ?
C1B C2B . 1.3947(19) ?
C1B C6B . 1.4068(19) ?
C1B C8B . 1.4382(19) ?
C2B C3B . 1.366(2) ?
C3B C4B . 1.3952(19) ?
C4B C5B . 1.3984(19) ?
C4B C7B . 1.4374(19) ?
C5B C6B . 1.4000(19) ?
C11B C16B . 1.398(2) ?
C11B C12B . 1.4011(19) ?
C11B C17B . 1.503(2) ?
C12B C13B . 1.390(2) ?
C13B C14B . 1.379(2) ?
C14B C15B . 1.389(2) ?
C14B H14B . 0.950000 ?
C15B C16B . 1.387(2) ?
C15B H15B . 0.950000 ?
C16B H16B . 0.950000 ?
C17B H17D . 0.980000 ?
C17B H17E . 0.980000 ?
C17B H17F . 0.980000 ?
C21B C22B . 1.3840(19) ?
C21B C26B . 1.393(2) ?
C22B C23B . 1.392(2) ?
C22B H22B . 0.950000 ?
C23B C24B . 1.390(2) ?
C23B H23B . 0.950000 ?
C24B C25B . 1.398(2) ?
C25B C26B . 1.381(2) ?
C25B H25B . 0.950000 ?
C26B H26B . 0.950000 ?
C27B C28B . 1.502(2) ?
C27B H27C . 0.990000 ?
C27B H27D . 0.990000 ?
C28B H28D . 0.980000 ?
C28B H28E . 0.980000 ?
C28B H28F . 0.980000 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C6A N3A C12A . . 112.27(11) ?
C6A N3A C21A . . 112.43(10) ?
C12A N3A C21A . . 114.73(10) ?
C5A O1A C13A . . 114.85(10) ?
C24A O2A C27A . . 117.38(11) ?
C2A C1A C6A . . 120.15(12) ?
C2A C1A C8A . . 119.98(12) ?
C6A C1A C8A . . 119.87(13) ?
F1A C2A C3A . . 119.37(13) ?
F1A C2A C1A . . 119.94(12) ?
C3A C2A C1A . . 120.64(13) ?
F2A C3A C2A . . 119.93(12) ?
F2A C3A C4A . . 119.77(12) ?
C2A C3A C4A . . 120.28(13) ?
C3A C4A C5A . . 119.01(12) ?
C3A C4A C7A . . 120.64(13) ?
C5A C4A C7A . . 120.13(13) ?
O1A C5A C6A . . 121.30(12) ?
O1A C5A C4A . . 117.30(12) ?
C6A C5A C4A . . 121.39(13) ?
C5A C6A C1A . . 118.28(13) ?
C5A C6A N3A . . 120.55(12) ?
C1A C6A N3A . . 121.14(12) ?
N1A C7A C4A . . 176.84(16) ?
N2A C8A C1A . . 177.03(15) ?
C16A C11A C12A . . 118.12(13) ?
C16A C11A C17A . . 121.01(13) ?
C12A C11A C17A . . 120.86(13) ?
C13A C12A C11A . . 119.27(13) ?
C13A C12A N3A . . 119.60(12) ?
C11A C12A N3A . . 121.12(12) ?
C14A C13A C12A . . 122.63(13) ?
C14A C13A O1A . . 116.68(12) ?
C12A C13A O1A . . 120.68(12) ?
C13A C14A C15A . . 117.71(13) ?
C13A C14A H14A . . 121.100000 ?
C15A C14A H14A . . 121.100000 ?
C16A C15A C14A . . 120.66(13) ?
C16A C15A H15A . . 119.700000 ?
C14A C15A H15A . . 119.700000 ?
C15A C16A C11A . . 121.59(14) ?
C15A C16A H16A . . 119.200000 ?
C11A C16A H16A . . 119.200000 ?
C11A C17A H17A . . 109.500000 ?
C11A C17A H17B . . 109.500000 ?
H17A C17A H17B . . 109.500000 ?
C11A C17A H17C . . 109.500000 ?
H17A C17A H17C . . 109.500000 ?
H17B C17A H17C . . 109.500000 ?
C22A C21A C26A . . 119.72(12) ?
C22A C21A N3A . . 119.59(12) ?
C26A C21A N3A . . 120.69(12) ?
C21A C22A C23A . . 120.96(13) ?
C21A C22A H22A . . 119.500000 ?
C23A C22A H22A . . 119.500000 ?
C22A C23A C24A . . 119.37(13) ?
C22A C23A H23A . . 120.300000 ?
C24A C23A H23A . . 120.300000 ?
O2A C24A C23A . . 124.42(12) ?
O2A C24A C25A . . 115.84(12) ?
C23A C24A C25A . . 119.74(13) ?
C26A C25A C24A . . 120.36(13) ?
C26A C25A H25A . . 119.800000 ?
C24A C25A H25A . . 119.800000 ?
C25A C26A C21A . . 119.81(13) ?
C25A C26A H26A . . 120.100000 ?
C21A C26A H26A . . 120.100000 ?
O2A C27A C28A . . 107.43(12) ?
O2A C27A H27A . . 110.200000 ?
C28A C27A H27A . . 110.200000 ?
O2A C27A H27B . . 110.200000 ?
C28A C27A H27B . . 110.200000 ?
H27A C27A H27B . . 108.500000 ?
C27A C28A H28A . . 109.500000 ?
C27A C28A H28B . . 109.500000 ?
H28A C28A H28B . . 109.500000 ?
C27A C28A H28C . . 109.500000 ?
H28A C28A H28C . . 109.500000 ?
H28B C28A H28C . . 109.500000 ?
C6B N3B C12B . . 113.99(11) ?
C6B N3B C21B . . 113.82(10) ?
C12B N3B C21B . . 113.49(10) ?
C5B O1B C13B . . 116.65(10) ?
C24B O2B C27B . . 117.96(11) ?
C2B C1B C6B . . 120.34(12) ?
C2B C1B C8B . . 116.94(12) ?
C6B C1B C8B . . 122.70(12) ?
F1B C2B C3B . . 119.63(12) ?
F1B C2B C1B . . 119.62(12) ?
C3B C2B C1B . . 120.75(12) ?
F2B C3B C2B . . 120.00(12) ?
F2B C3B C4B . . 119.64(12) ?
C2B C3B C4B . . 120.36(12) ?
C3B C4B C5B . . 119.31(12) ?
C3B C4B C7B . . 118.34(12) ?
C5B C4B C7B . . 122.33(12) ?
O1B C5B C4B . . 116.83(12) ?
O1B C5B C6B . . 122.05(12) ?
C4B C5B C6B . . 121.09(12) ?
C5B C6B C1B . . 118.07(12) ?
C5B C6B N3B . . 120.72(12) ?
C1B C6B N3B . . 121.20(12) ?
N1B C7B C4B . . 176.48(14) ?
N2B C8B C1B . . 175.29(15) ?
C16B C11B C12B . . 118.16(13) ?
C16B C11B C17B . . 120.31(13) ?
C12B C11B C17B . . 121.50(13) ?
C13B C12B C11B . . 118.92(12) ?
C13B C12B N3B . . 120.58(12) ?
C11B C12B N3B . . 120.50(12) ?
C14B C13B C12B . . 122.67(12) ?
C14B C13B O1B . . 116.43(12) ?
C12B C13B O1B . . 120.89(12) ?
C13B C14B C15B . . 118.39(13) ?
C13B C14B H14B . . 120.800000 ?
C15B C14B H14B . . 120.800000 ?
C16B C15B C14B . . 119.82(13) ?
C16B C15B H15B . . 120.100000 ?
C14B C15B H15B . . 120.100000 ?
C15B C16B C11B . . 121.79(13) ?
C15B C16B H16B . . 119.100000 ?
C11B C16B H16B . . 119.100000 ?
C11B C17B H17D . . 109.500000 ?
C11B C17B H17E . . 109.500000 ?
H17D C17B H17E . . 109.500000 ?
C11B C17B H17F . . 109.500000 ?
H17D C17B H17F . . 109.500000 ?
H17E C17B H17F . . 109.500000 ?
C22B C21B C26B . . 119.75(13) ?
C22B C21B N3B . . 120.50(12) ?
C26B C21B N3B . . 119.74(12) ?
C21B C22B C23B . . 120.50(13) ?
C21B C22B H22B . . 119.800000 ?
C23B C22B H22B . . 119.800000 ?
C24B C23B C22B . . 119.73(13) ?
C24B C23B H23B . . 120.100000 ?
C22B C23B H23B . . 120.100000 ?
O2B C24B C23B . . 124.55(13) ?
O2B C24B C25B . . 115.75(12) ?
C23B C24B C25B . . 119.70(13) ?
C26B C25B C24B . . 120.19(13) ?
C26B C25B H25B . . 119.900000 ?
C24B C25B H25B . . 119.900000 ?
C25B C26B C21B . . 120.12(13) ?
C25B C26B H26B . . 119.900000 ?
C21B C26B H26B . . 119.900000 ?
O2B C27B C28B . . 107.64(12) ?
O2B C27B H27C . . 110.200000 ?
C28B C27B H27C . . 110.200000 ?
O2B C27B H27D . . 110.200000 ?
C28B C27B H27D . . 110.200000 ?
H27C C27B H27D . . 108.500000 ?
C27B C28B H28D . . 109.500000 ?
C27B C28B H28E . . 109.500000 ?
H28D C28B H28E . . 109.500000 ?
C27B C28B H28F . . 109.500000 ?
H28D C28B H28F . . 109.500000 ?
H28E C28B H28F . . 109.500000 ?

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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C6A C1A C2A F1A . . . . 175.13(11) ?
C8A C1A C2A F1A . . . . -5.03(19) ?
C6A C1A C2A C3A . . . . -2.4(2) ?
C8A C1A C2A C3A . . . . 177.46(12) ?
F1A C2A C3A F2A . . . . 0.07(19) ?
C1A C2A C3A F2A . . . . 177.60(12) ?
F1A C2A C3A C4A . . . . -178.38(12) ?
C1A C2A C3A C4A . . . . -0.9(2) ?
F2A C3A C4A C5A . . . . -177.67(12) ?
C2A C3A C4A C5A . . . . 0.8(2) ?
F2A C3A C4A C7A . . . . -3.06(19) ?
C2A C3A C4A C7A . . . . 175.39(13) ?
C13A O1A C5A C6A . . . . -22.71(17) ?
C13A O1A C5A C4A . . . . 158.76(11) ?
C3A C4A C5A O1A . . . . -178.91(11) ?
C7A C4A C5A O1A . . . . 6.45(19) ?
C3A C4A C5A C6A . . . . 2.6(2) ?
C7A C4A C5A C6A . . . . -172.07(12) ?
O1A C5A C6A C1A . . . . 175.85(11) ?
C4A C5A C6A C1A . . . . -5.68(19) ?
O1A C5A C6A N3A . . . . -5.69(19) ?
C4A C5A C6A N3A . . . . 172.78(12) ?
C2A C1A C6A C5A . . . . 5.55(19) ?
C8A C1A C6A C5A . . . . -174.29(12) ?
C2A C1A C6A N3A . . . . -172.90(12) ?
C8A C1A C6A N3A . . . . 7.26(19) ?
C12A N3A C6A C5A . . . . 28.31(17) ?
C21A N3A C6A C5A . . . . -102.84(14) ?
C12A N3A C6A C1A . . . . -153.27(12) ?
C21A N3A C6A C1A . . . . 75.58(15) ?
C16A C11A C12A C13A . . . . 0.98(19) ?
C17A C11A C12A C13A . . . . -178.15(13) ?
C16A C11A C12A N3A . . . . -177.35(12) ?
C17A C11A C12A N3A . . . . 3.5(2) ?
C6A N3A C12A C13A . . . . -23.18(17) ?
C21A N3A C12A C13A . . . . 106.80(14) ?
C6A N3A C12A C11A . . . . 155.15(12) ?
C21A N3A C12A C11A . . . . -74.87(16) ?
C11A C12A C13A C14A . . . . -1.9(2) ?
N3A C12A C13A C14A . . . . 176.50(12) ?
C11A C12A C13A O1A . . . . 177.61(11) ?
N3A C12A C13A O1A . . . . -4.03(19) ?
C5A O1A C13A C14A . . . . -152.98(12) ?
C5A O1A C13A C12A . . . . 27.52(17) ?
C12A C13A C14A C15A . . . . 1.3(2) ?
O1A C13A C14A C15A . . . . -178.23(12) ?
C13A C14A C15A C16A . . . . 0.2(2) ?
C14A C15A C16A C11A . . . . -1.0(2) ?
C12A C11A C16A C15A . . . . 0.4(2) ?
C17A C11A C16A C15A . . . . 179.54(13) ?
C6A N3A C21A C22A . . . . 74.01(16) ?
C12A N3A C21A C22A . . . . -55.89(17) ?
C6A N3A C21A C26A . . . . -105.84(14) ?
C12A N3A C21A C26A . . . . 124.25(14) ?
C26A C21A C22A C23A . . . . -1.0(2) ?
N3A C21A C22A C23A . . . . 179.11(12) ?
C21A C22A C23A C24A . . . . 0.6(2) ?
C27A O2A C24A C23A . . . . 7.5(2) ?
C27A O2A C24A C25A . . . . -172.37(13) ?
C22A C23A C24A O2A . . . . -178.84(13) ?
C22A C23A C24A C25A . . . . 1.0(2) ?
O2A C24A C25A C26A . . . . 177.57(13) ?
C23A C24A C25A C26A . . . . -2.3(2) ?
C24A C25A C26A C21A . . . . 1.9(2) ?
C22A C21A C26A C25A . . . . -0.3(2) ?
N3A C21A C26A C25A . . . . 179.61(12) ?
C24A O2A C27A C28A . . . . 169.63(13) ?
C6B C1B C2B F1B . . . . -177.93(12) ?
C8B C1B C2B F1B . . . . 3.41(19) ?
C6B C1B C2B C3B . . . . 2.7(2) ?
C8B C1B C2B C3B . . . . -175.92(13) ?
F1B C2B C3B F2B . . . . 0.4(2) ?
C1B C2B C3B F2B . . . . 179.75(12) ?
F1B C2B C3B C4B . . . . 179.89(12) ?
C1B C2B C3B C4B . . . . -0.8(2) ?
F2B C3B C4B C5B . . . . 178.09(12) ?
C2B C3B C4B C5B . . . . -1.4(2) ?
F2B C3B C4B C7B . . . . -0.63(19) ?
C2B C3B C4B C7B . . . . 179.90(13) ?
C13B O1B C5B C4B . . . . -164.35(11) ?
C13B O1B C5B C6B . . . . 17.36(18) ?
C3B C4B C5B O1B . . . . -176.70(12) ?
C7B C4B C5B O1B . . . . 1.97(19) ?
C3B C4B C5B C6B . . . . 1.6(2) ?
C7B C4B C5B C6B . . . . -179.73(13) ?
O1B C5B C6B C1B . . . . 178.52(12) ?
C4B C5B C6B C1B . . . . 0.31(19) ?
O1B C5B C6B N3B . . . . -0.46(19) ?
C4B C5B C6B N3B . . . . -178.68(12) ?
C2B C1B C6B C5B . . . . -2.5(2) ?
C8B C1B C6B C5B . . . . 176.12(12) ?
C2B C1B C6B N3B . . . . 176.52(12) ?
C8B C1B C6B N3B . . . . -4.9(2) ?
C12B N3B C6B C5B . . . . -18.20(17) ?
C21B N3B C6B C5B . . . . 114.14(14) ?
C12B N3B C6B C1B . . . . 162.85(12) ?
C21B N3B C6B C1B . . . . -64.82(16) ?
C16B C11B C12B C13B . . . . 5.7(2) ?
C17B C11B C12B C13B . . . . -172.16(12) ?
C16B C11B C12B N3B . . . . -174.77(12) ?
C17B C11B C12B N3B . . . . 7.4(2) ?
C6B N3B C12B C13B . . . . 20.59(17) ?
C21B N3B C12B C13B . . . . -111.90(14) ?
C6B N3B C12B C11B . . . . -158.96(12) ?
C21B N3B C12B C11B . . . . 68.55(16) ?
C11B C12B C13B C14B . . . . -4.7(2) ?
N3B C12B C13B C14B . . . . 175.73(12) ?
C11B C12B C13B O1B . . . . 174.95(12) ?
N3B C12B C13B O1B . . . . -4.61(19) ?
C5B O1B C13B C14B . . . . 164.99(12) ?
C5B O1B C13B C12B . . . . -14.69(17) ?
C12B C13B C14B C15B . . . . 0.4(2) ?
O1B C13B C14B C15B . . . . -179.28(12) ?
C13B C14B C15B C16B . . . . 2.8(2) ?
C14B C15B C16B C11B . . . . -1.7(2) ?
C12B C11B C16B C15B . . . . -2.6(2) ?
C17B C11B C16B C15B . . . . 175.25(13) ?
C6B N3B C21B C22B . . . . 113.74(14) ?
C12B N3B C21B C22B . . . . -113.69(14) ?
C6B N3B C21B C26B . . . . -67.30(16) ?
C12B N3B C21B C26B . . . . 65.28(16) ?
C26B C21B C22B C23B . . . . -0.9(2) ?
N3B C21B C22B C23B . . . . 178.11(12) ?
C21B C22B C23B C24B . . . . 0.8(2) ?
C27B O2B C24B C23B . . . . 7.76(19) ?
C27B O2B C24B C25B . . . . -172.82(12) ?
C22B C23B C24B O2B . . . . 179.39(13) ?
C22B C23B C24B C25B . . . . 0.0(2) ?
O2B C24B C25B C26B . . . . 179.79(12) ?
C23B C24B C25B C26B . . . . -0.8(2) ?
C24B C25B C26B C21B . . . . 0.7(2) ?
C22B C21B C26B C25B . . . . 0.1(2) ?
N3B C21B C26B C25B . . . . -178.90(12) ?
C24B O2B C27B C28B . . . . -172.52(11) ?

