# Supplementary Information (SI) for ChemComm.
# 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_24106_a
_database_code_depnum_ccdc_archive 'CCDC 2426004'
loop_
_audit_author_name
_audit_author_address
'Jeffery A. Bertke'
;Georgetown University
United States of America
;
_audit_update_record             
;
2025-02-21 deposited with the CCDC.	2025-04-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/1
_shelx_SHELXL_version_number     2019/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H15 F N2 O5'
_chemical_formula_sum            'C24 H15 F N2 O5'
_chemical_formula_weight         430.38

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

_space_group_crystal_system      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                   8.6510(4)
_cell_length_b                   10.0429(4)
_cell_length_c                   13.0902(6)
_cell_angle_alpha                106.1230(10)
_cell_angle_beta                 95.5930(10)
_cell_angle_gamma                112.0220(10)
_cell_volume                     986.56(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9975
_cell_measurement_theta_min      2.61
_cell_measurement_theta_max      28.28
_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.449
_exptl_crystal_F_000             444
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.295
_exptl_crystal_size_mid          0.124
_exptl_crystal_size_min          0.091
_exptl_absorpt_coefficient_mu    0.109
_shelx_estimated_absorpt_T_min   0.969
_shelx_estimated_absorpt_T_max   0.990
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.97979
_exptl_absorpt_correction_T_max  0.99436
_exptl_absorpt_process_details   'SADABS V2016/2 (Bruker, 2016)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  'multilayer mirrors'
_diffrn_measurement_device_type  'Bruker APEX DUO/ApexII CCD'
_diffrn_measurement_method       'profile data from φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            49141
_diffrn_reflns_av_unetI/netI     0.0151
_diffrn_reflns_av_R_equivalents  0.0314
_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
_diffrn_reflns_theta_min         2.757
_diffrn_reflns_theta_max         28.304
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4889
_reflns_number_gt                4226
_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       'APEX4 V2016.5-0 (Bruker, 2016)'
_computing_cell_refinement       'SAINT V8.37A (Bruker, 2005)'
_computing_data_reduction        
; 
SAINT V8.37A, XPREP v2014/2, SADABS V2016/2 (Bruker, 2016) 
;
_computing_structure_solution    'SHELX-2014-5 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2019)'
_computing_molecular_graphics    'SHELXLE v932 (Hubschle, 2011)'
_computing_publication_material  'XCIF V2014-2 (Bruker, 2014)'

_refine_special_details          
; 
Structure was phased by intrinsic methods (Sheldrick, 2015).  Systematic 
conditions suggested the ambiguous space group.  The space group choice was 
confirmed by successful convergence of the full-matrix least-squares 
refinement on F².  The final map had no significant features.  A final 
analysis of variance between observed and calculated structure factors showed 
little dependence on amplitude and resolution. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0385P)²+0.5379P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     intrinsic
_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         4889
_refine_ls_number_parameters     289
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0432
_refine_ls_R_factor_gt           0.0358
_refine_ls_wR_factor_ref         0.0904
_refine_ls_wR_factor_gt          0.0853
_refine_ls_goodness_of_fit_ref   1.008
_refine_ls_restrained_S_all      1.008
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.34137(9) -0.03819(8) 0.22815(6) 0.02114(16) Uani 1 1 d . . . . .
O1 O 0.27888(11) 0.21171(11) 0.18609(7) 0.02218(19) Uani 1 1 d . . . . .
O2 O 0.54904(11) 0.36885(10) 0.59685(7) 0.02130(18) Uani 1 1 d . . . . .
O3 O 0.33514(12) 0.17440(11) 0.61379(7) 0.0262(2) Uani 1 1 d . . . . .
O4 O 0.11665(11) -0.02316(11) 0.37443(8) 0.0257(2) Uani 1 1 d . . . . .
O5 O 0.29215(12) -0.11553(10) 0.42114(8) 0.0274(2) Uani 1 1 d . . . . .
N1 N 0.49989(11) 0.19716(10) 0.10421(7) 0.01328(18) Uani 1 1 d . . . . .
N2 N 0.25933(13) -0.01232(11) 0.40742(8) 0.0182(2) Uani 1 1 d . . . . .
C1 C 0.40154(14) 0.18219(12) 0.17920(9) 0.0150(2) Uani 1 1 d . . . . .
C2 C 0.47112(14) 0.11009(12) 0.25441(9) 0.0147(2) Uani 1 1 d . . . . .
C3 C 0.62362(14) 0.10052(12) 0.21255(9) 0.0139(2) Uani 1 1 d . . . . .
C4 C 0.74495(14) 0.05625(12) 0.24983(9) 0.0161(2) Uani 1 1 d . . . . .
H4 H 0.739553 0.023365 0.311321 0.019 Uiso 1 1 calc R U . . .
C5 C 0.87611(14) 0.06137(12) 0.19416(9) 0.0170(2) Uani 1 1 d . . . . .
H5 H 0.962204 0.032993 0.218692 0.020 Uiso 1 1 calc R U . . .
C6 C 0.88162(14) 0.10766(12) 0.10316(9) 0.0165(2) Uani 1 1 d . . . . .
H6 H 0.970991 0.109011 0.066080 0.020 Uiso 1 1 calc R U . . .
C7 C 0.75838(14) 0.15234(12) 0.06493(9) 0.0147(2) Uani 1 1 d . . . . .
H7 H 0.762042 0.183394 0.002622 0.018 Uiso 1 1 calc R U . . .
C8 C 0.63134(13) 0.14921(11) 0.12190(8) 0.0129(2) Uani 1 1 d . . . . .
C9 C 0.47654(14) 0.26312(12) 0.02024(9) 0.0153(2) Uani 1 1 d . . . . .
H9A H 0.369447 0.277645 0.019594 0.018 Uiso 1 1 calc R U . . .
H9B H 0.465502 0.191417 -0.052290 0.018 Uiso 1 1 calc R U . . .
C10 C 0.62559(14) 0.41510(12) 0.04077(9) 0.0148(2) Uani 1 1 d . . . . .
C11 C 0.71956(15) 0.43811(13) -0.03816(10) 0.0184(2) Uani 1 1 d . . . . .
H11 H 0.688227 0.358858 -0.106491 0.022 Uiso 1 1 calc R U . . .
C12 C 0.85972(16) 0.57726(14) -0.01731(11) 0.0220(2) Uani 1 1 d . . . . .
H12 H 0.923009 0.592746 -0.071604 0.026 Uiso 1 1 calc R U . . .
C13 C 0.90662(15) 0.69297(14) 0.08275(11) 0.0217(2) Uani 1 1 d . . . . .
H13 H 1.003885 0.786552 0.097635 0.026 Uiso 1 1 calc R U . . .
C14 C 0.81117(16) 0.67191(13) 0.16128(10) 0.0204(2) Uani 1 1 d . . . . .
H14 H 0.842138 0.751652 0.229301 0.025 Uiso 1 1 calc R U . . .
C15 C 0.67038(15) 0.53392(13) 0.13997(9) 0.0176(2) Uani 1 1 d . . . . .
H15 H 0.604251 0.520326 0.193151 0.021 Uiso 1 1 calc R U . . .
C16 C 0.49984(14) 0.19722(12) 0.37473(9) 0.0141(2) Uani 1 1 d . . . . .
C17 C 0.40282(14) 0.14097(13) 0.44034(9) 0.0158(2) Uani 1 1 d . . . . .
C18 C 0.42306(15) 0.22475(14) 0.55581(9) 0.0189(2) Uani 1 1 d . . . . .
C19 C 0.65288(15) 0.43313(13) 0.53361(9) 0.0175(2) Uani 1 1 d . . . . .
C20 C 0.77471(16) 0.58238(14) 0.58673(10) 0.0222(2) Uani 1 1 d . . . . .
H20 H 0.784040 0.633182 0.661565 0.027 Uiso 1 1 calc R U . . .
C21 C 0.88204(16) 0.65560(14) 0.52879(10) 0.0227(3) Uani 1 1 d . . . . .
H21 H 0.965744 0.757592 0.563990 0.027 Uiso 1 1 calc R U . . .
C22 C 0.86807(15) 0.58048(13) 0.41890(10) 0.0201(2) Uani 1 1 d . . . . .
H22 H 0.942065 0.631393 0.379508 0.024 Uiso 1 1 calc R U . . .
C23 C 0.74632(15) 0.43166(13) 0.36726(9) 0.0174(2) Uani 1 1 d . . . . .
H23 H 0.738127 0.381515 0.292490 0.021 Uiso 1 1 calc R U . . .
C24 C 0.63430(14) 0.35310(12) 0.42338(9) 0.0152(2) 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.
;

_exptl_special_details           
; 
One distinct cell was identified using APEX4 (Bruker, 2016).  Thirteen 
frame series were integrated and filtered for statistical outliers using SAINT 
(Bruker, 2016) then corrected for absorption by integration using SAINT/SADABS 
v2014/2 (Bruker, 2016) to sort, merge, and scale the combined data.  No decay 
correction was applied.    
;

loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1.00 1.00 -1.00 0.0660
-1.00 -1.00 1.00 0.0210
-1.00 1.00 1.00 0.0910
1.00 -1.00 -1.00 0.1260
0.00 1.00 -1.00 0.0670
0.00 -1.00 1.00 0.0240
0.00 1.00 1.00 0.0890
-1.00 0.00 -1.00 0.0590
1.00 -1.00 1.00 0.0510
-1.00 1.00 -1.00 0.0230
1.00 0.00 0.00 0.0500

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C2 1.4080(12) . ?
O1 C1 1.2090(14) . ?
O2 C18 1.3572(15) . ?
O2 C19 1.3843(14) . ?
O3 C18 1.2031(15) . ?
O4 N2 1.2211(13) . ?
O5 N2 1.2252(13) . ?
N1 C1 1.3634(14) . ?
N1 C8 1.4142(14) . ?
N1 C9 1.4662(14) . ?
N2 C17 1.4802(14) . ?
C1 C2 1.5695(15) . ?
C2 C3 1.5023(15) . ?
C2 C16 1.5176(15) . ?
C3 C4 1.3813(15) . ?
C3 C8 1.4018(15) . ?
C4 C5 1.3998(16) . ?
C4 H4 0.9500 . ?
C5 C6 1.3926(16) . ?
C5 H5 0.9500 . ?
C6 C7 1.4029(15) . ?
C6 H6 0.9500 . ?
C7 C8 1.3827(15) . ?
C7 H7 0.9500 . ?
C9 C10 1.5143(15) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.3919(16) . ?
C10 C15 1.3981(16) . ?
C11 C12 1.3966(17) . ?
C11 H11 0.9500 . ?
C12 C13 1.3886(18) . ?
C12 H12 0.9500 . ?
C13 C14 1.3923(17) . ?
C13 H13 0.9500 . ?
C14 C15 1.3911(16) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
C16 C17 1.3474(15) . ?
C16 C24 1.4648(15) . ?
C17 C18 1.4680(16) . ?
C19 C20 1.3909(16) . ?
C19 C24 1.4027(15) . ?
C20 C21 1.3832(18) . ?
C20 H20 0.9500 . ?
C21 C22 1.3957(17) . ?
C21 H21 0.9500 . ?
C22 C23 1.3855(16) . ?
C22 H22 0.9500 . ?
C23 C24 1.4102(16) . ?
C23 H23 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
C18 O2 C19 121.96(9) . . ?
C1 N1 C8 111.48(9) . . ?
C1 N1 C9 123.56(9) . . ?
C8 N1 C9 124.87(9) . . ?
O4 N2 O5 125.49(10) . . ?
O4 N2 C17 117.01(10) . . ?
O5 N2 C17 117.37(10) . . ?
O1 C1 N1 127.94(11) . . ?
O1 C1 C2 124.91(10) . . ?
N1 C1 C2 107.09(9) . . ?
F1 C2 C3 109.46(9) . . ?
F1 C2 C16 109.15(8) . . ?
C3 C2 C16 117.63(9) . . ?
F1 C2 C1 104.72(8) . . ?
C3 C2 C1 102.88(8) . . ?
C16 C2 C1 112.14(9) . . ?
C4 C3 C8 121.17(10) . . ?
C4 C3 C2 130.82(10) . . ?
C8 C3 C2 108.00(9) . . ?
C3 C4 C5 117.91(10) . . ?
C3 C4 H4 121.0 . . ?
C5 C4 H4 121.0 . . ?
C6 C5 C4 120.65(10) . . ?
C6 C5 H5 119.7 . . ?
C4 C5 H5 119.7 . . ?
C5 C6 C7 121.59(10) . . ?
C5 C6 H6 119.2 . . ?
C7 C6 H6 119.2 . . ?
C8 C7 C6 117.09(10) . . ?
C8 C7 H7 121.5 . . ?
C6 C7 H7 121.5 . . ?
C7 C8 C3 121.58(10) . . ?
C7 C8 N1 127.97(10) . . ?
C3 C8 N1 110.40(9) . . ?
N1 C9 C10 111.41(9) . . ?
N1 C9 H9A 109.3 . . ?
C10 C9 H9A 109.3 . . ?
N1 C9 H9B 109.3 . . ?
C10 C9 H9B 109.3 . . ?
H9A C9 H9B 108.0 . . ?
C11 C10 C15 119.32(10) . . ?
C11 C10 C9 120.68(10) . . ?
C15 C10 C9 120.00(10) . . ?
C10 C11 C12 120.26(11) . . ?
C10 C11 H11 119.9 . . ?
C12 C11 H11 119.9 . . ?
C13 C12 C11 120.03(11) . . ?
C13 C12 H12 120.0 . . ?
C11 C12 H12 120.0 . . ?
C12 C13 C14 120.03(11) . . ?
C12 C13 H13 120.0 . . ?
C14 C13 H13 120.0 . . ?
C15 C14 C13 119.89(11) . . ?
C15 C14 H14 120.1 . . ?
C13 C14 H14 120.1 . . ?
C14 C15 C10 120.42(11) . . ?
C14 C15 H15 119.8 . . ?
C10 C15 H15 119.8 . . ?
C17 C16 C24 116.91(10) . . ?
C17 C16 C2 123.35(10) . . ?
C24 C16 C2 119.69(9) . . ?
C16 C17 C18 124.60(10) . . ?
C16 C17 N2 125.64(10) . . ?
C18 C17 N2 109.75(9) . . ?
O3 C18 O2 119.50(11) . . ?
O3 C18 C17 124.32(11) . . ?
O2 C18 C17 116.18(10) . . ?
O2 C19 C20 115.30(10) . . ?
O2 C19 C24 121.97(10) . . ?
C20 C19 C24 122.73(11) . . ?
C21 C20 C19 118.89(11) . . ?
C21 C20 H20 120.6 . . ?
C19 C20 H20 120.6 . . ?
C20 C21 C22 120.37(11) . . ?
C20 C21 H21 119.8 . . ?
C22 C21 H21 119.8 . . ?
C23 C22 C21 120.02(11) . . ?
C23 C22 H22 120.0 . . ?
C21 C22 H22 120.0 . . ?
C22 C23 C24 121.36(11) . . ?
C22 C23 H23 119.3 . . ?
C24 C23 H23 119.3 . . ?
C19 C24 C23 116.63(10) . . ?
C19 C24 C16 118.37(10) . . ?
C23 C24 C16 124.99(10) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C8 N1 C1 O1 -179.33(11) . . . . ?
C9 N1 C1 O1 3.92(18) . . . . ?
C8 N1 C1 C2 -2.14(11) . . . . ?
C9 N1 C1 C2 -178.89(9) . . . . ?
O1 C1 C2 F1 66.50(13) . . . . ?
N1 C1 C2 F1 -110.80(9) . . . . ?
O1 C1 C2 C3 -179.08(10) . . . . ?
N1 C1 C2 C3 3.62(11) . . . . ?
O1 C1 C2 C16 -51.73(14) . . . . ?
N1 C1 C2 C16 130.97(9) . . . . ?
F1 C2 C3 C4 -73.83(14) . . . . ?
C16 C2 C3 C4 51.46(16) . . . . ?
C1 C2 C3 C4 175.24(11) . . . . ?
F1 C2 C3 C8 107.11(10) . . . . ?
C16 C2 C3 C8 -127.61(10) . . . . ?
C1 C2 C3 C8 -3.83(11) . . . . ?
C8 C3 C4 C5 -0.05(15) . . . . ?
C2 C3 C4 C5 -179.02(10) . . . . ?
C3 C4 C5 C6 -0.92(16) . . . . ?
C4 C5 C6 C7 0.80(17) . . . . ?
C5 C6 C7 C8 0.32(16) . . . . ?
C6 C7 C8 C3 -1.31(15) . . . . ?
C6 C7 C8 N1 175.79(10) . . . . ?
C4 C3 C8 C7 1.20(16) . . . . ?
C2 C3 C8 C7 -179.62(9) . . . . ?
C4 C3 C8 N1 -176.35(9) . . . . ?
C2 C3 C8 N1 2.82(12) . . . . ?
C1 N1 C8 C7 -177.72(10) . . . . ?
C9 N1 C8 C7 -1.03(17) . . . . ?
C1 N1 C8 C3 -0.36(12) . . . . ?
C9 N1 C8 C3 176.33(9) . . . . ?
C1 N1 C9 C10 111.70(11) . . . . ?
C8 N1 C9 C10 -64.60(13) . . . . ?
N1 C9 C10 C11 122.90(11) . . . . ?
N1 C9 C10 C15 -56.91(13) . . . . ?
C15 C10 C11 C12 1.58(17) . . . . ?
C9 C10 C11 C12 -178.24(10) . . . . ?
C10 C11 C12 C13 0.45(18) . . . . ?
C11 C12 C13 C14 -1.75(18) . . . . ?
C12 C13 C14 C15 1.01(18) . . . . ?
C13 C14 C15 C10 1.04(17) . . . . ?
C11 C10 C15 C14 -2.33(17) . . . . ?
C9 C10 C15 C14 177.49(10) . . . . ?
F1 C2 C16 C17 -5.25(15) . . . . ?
C3 C2 C16 C17 -130.69(11) . . . . ?
C1 C2 C16 C17 110.32(12) . . . . ?
F1 C2 C16 C24 177.40(9) . . . . ?
C3 C2 C16 C24 51.96(14) . . . . ?
C1 C2 C16 C24 -67.03(12) . . . . ?
C24 C16 C17 C18 -0.02(16) . . . . ?
C2 C16 C17 C18 -177.43(10) . . . . ?
C24 C16 C17 N2 179.11(10) . . . . ?
C2 C16 C17 N2 1.70(17) . . . . ?
O4 N2 C17 C16 -91.04(14) . . . . ?
O5 N2 C17 C16 92.86(14) . . . . ?
O4 N2 C17 C18 88.20(12) . . . . ?
O5 N2 C17 C18 -87.90(12) . . . . ?
C19 O2 C18 O3 -179.34(11) . . . . ?
C19 O2 C18 C17 -0.16(15) . . . . ?
C16 C17 C18 O3 179.36(11) . . . . ?
N2 C17 C18 O3 0.12(16) . . . . ?
C16 C17 C18 O2 0.22(17) . . . . ?
N2 C17 C18 O2 -179.03(9) . . . . ?
C18 O2 C19 C20 179.18(10) . . . . ?
C18 O2 C19 C24 -0.11(17) . . . . ?
O2 C19 C20 C21 -179.13(11) . . . . ?
C24 C19 C20 C21 0.16(18) . . . . ?
C19 C20 C21 C22 -0.09(18) . . . . ?
C20 C21 C22 C23 -0.07(19) . . . . ?
C21 C22 C23 C24 0.17(18) . . . . ?
O2 C19 C24 C23 179.18(10) . . . . ?
C20 C19 C24 C23 -0.07(17) . . . . ?
O2 C19 C24 C16 0.32(16) . . . . ?
C20 C19 C24 C16 -178.92(11) . . . . ?
C22 C23 C24 C19 -0.10(17) . . . . ?
C22 C23 C24 C16 178.67(11) . . . . ?
C17 C16 C24 C19 -0.25(15) . . . . ?
C2 C16 C24 C19 177.27(10) . . . . ?
C17 C16 C24 C23 -179.00(11) . . . . ?
C2 C16 C24 C23 -1.48(16) . . . . ?

_refine_diff_density_max         0.364
_refine_diff_density_min         -0.216
_refine_diff_density_rms         0.043



####################################################################### 
# 
# 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_24108_a
_database_code_depnum_ccdc_archive 'CCDC 2426009'
loop_
_audit_author_name
_audit_author_address
'Jeffery A. Bertke'
;Georgetown University
United States of America
;
_audit_update_record             
;
2025-02-21 deposited with the CCDC.	2025-04-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/1
_shelx_SHELXL_version_number     2019/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H10 Br F N2 O5'
_chemical_formula_sum            'C18 H10 Br F N2 O5'
_chemical_formula_weight         433.19

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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      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                   8.0949(7)
_cell_length_b                   8.6881(7)
_cell_length_c                   12.6768(10)
_cell_angle_alpha                74.9290(10)
_cell_angle_beta                 84.954(2)
_cell_angle_gamma                73.257(2)
_cell_volume                     824.31(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9898
_cell_measurement_theta_min      2.53
_cell_measurement_theta_max      26.46
_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.745
_exptl_crystal_F_000             432
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.174
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.048
_exptl_absorpt_coefficient_mu    2.539
_shelx_estimated_absorpt_T_min   0.666
_shelx_estimated_absorpt_T_max   0.888
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.65376
_exptl_absorpt_correction_T_max  0.87845
_exptl_absorpt_process_details   'SADABS V2016/2 (Bruker, 2016)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  'multilayer mirrors'
_diffrn_measurement_device_type  'Bruker APEX DUO/ApexII CCD'
_diffrn_measurement_method       'profile data from φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            37785
_diffrn_reflns_av_unetI/netI     0.0166
_diffrn_reflns_av_R_equivalents  0.0364
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_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         2.526
_diffrn_reflns_theta_max         26.464
_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             3391
_reflns_number_gt                3122
_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       'APEX4 V2016.5-0 (Bruker, 2016)'
_computing_cell_refinement       'SAINT V8.37A (Bruker, 2005)'
_computing_data_reduction        
; 
SAINT V8.37A, XPREP v2014/2, SADABS V2016/2 (Bruker, 2016) 
;
_computing_structure_solution    'SHELX-2014-5 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2019)'
_computing_molecular_graphics    'SHELXLE v932 (Hubschle, 2011)'
_computing_publication_material  'XCIF V2014-2 (Bruker, 2014)'

_refine_special_details          
; 
Structure was phased by intrinsic methods (Sheldrick, 2015).  Systematic 
conditions suggested the ambiguous space group.  The space group choice was 
confirmed by successful convergence of the full-matrix least-squares refinement 
on F².  The final map had no significant features.  A final analysis of 
variance between observed and calculated structure factors showed little 
dependence on amplitude and resolution. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0243P)²+0.7173P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     intrinsic
_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         3391
_refine_ls_number_parameters     245
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0272
_refine_ls_R_factor_gt           0.0237
_refine_ls_wR_factor_ref         0.0582
_refine_ls_wR_factor_gt          0.0570
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_restrained_S_all      1.066
_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
Br1 Br 0.49162(3) 0.83307(2) 0.43576(2) 0.02510(7) Uani 1 1 d . . . . .
F1 F 0.86864(13) 0.27240(12) 0.90852(8) 0.0164(2) Uani 1 1 d . . . . .
O1 O 0.87387(16) 0.60186(16) 0.78295(10) 0.0178(3) Uani 1 1 d . . . . .
O2 O 1.01213(17) 0.16532(16) 0.54338(10) 0.0210(3) Uani 1 1 d . . . . .
O3 O 1.14095(18) -0.07200(17) 0.65760(12) 0.0261(3) Uani 1 1 d . . . . .
O4 O 1.13807(17) -0.01477(16) 0.87605(11) 0.0230(3) Uani 1 1 d . . . . .
O5 O 0.88416(18) -0.05569(17) 0.88311(11) 0.0246(3) Uani 1 1 d . . . . .
N1 N 0.58627(18) 0.62360(18) 0.82597(12) 0.0138(3) Uani 1 1 d . . . . .
N2 N 0.9936(2) 0.01407(18) 0.84097(13) 0.0177(3) Uani 1 1 d . . . . .
C1 C 0.7526(2) 0.5438(2) 0.80487(13) 0.0135(3) Uani 1 1 d . . . . .
C2 C 0.7608(2) 0.3574(2) 0.81875(14) 0.0133(3) Uani 1 1 d . . . . .
C3 C 0.5776(2) 0.3542(2) 0.84826(13) 0.0142(3) Uani 1 1 d . . . . .
C4 C 0.5036(2) 0.2239(2) 0.87488(14) 0.0178(4) Uani 1 1 d . . . . .
H4 H 0.568445 0.115478 0.870609 0.021 Uiso 1 1 calc R U . . .
C5 C 0.3303(2) 0.2567(3) 0.90833(15) 0.0212(4) Uani 1 1 d . . . . .
H5 H 0.276478 0.169267 0.928477 0.025 Uiso 1 1 calc R U . . .
C6 C 0.2364(2) 0.4165(3) 0.91221(15) 0.0211(4) Uani 1 1 d . . . . .
H6 H 0.118727 0.436040 0.934734 0.025 Uiso 1 1 calc R U . . .
C7 C 0.3092(2) 0.5491(2) 0.88418(14) 0.0186(4) Uani 1 1 d . . . . .
H7 H 0.243690 0.658296 0.886147 0.022 Uiso 1 1 calc R U . . .
C8 C 0.4819(2) 0.5137(2) 0.85328(13) 0.0144(3) Uani 1 1 d . . . . .
C9 C 0.5267(2) 0.8006(2) 0.82014(16) 0.0198(4) Uani 1 1 d . . . . .
H9A H 0.624740 0.848302 0.803556 0.030 Uiso 1 1 calc R U . . .
H9B H 0.474498 0.817632 0.890413 0.030 Uiso 1 1 calc R U . . .
H9C H 0.440838 0.854946 0.762527 0.030 Uiso 1 1 calc R U . . .
C10 C 0.8411(2) 0.2883(2) 0.72188(14) 0.0137(3) Uani 1 1 d . . . . .
C11 C 0.9508(2) 0.1350(2) 0.73460(15) 0.0159(4) Uani 1 1 d . . . . .
C12 C 1.0426(2) 0.0640(2) 0.64547(15) 0.0192(4) Uani 1 1 d . . . . .
C13 C 0.8926(2) 0.3187(2) 0.52452(15) 0.0178(4) Uani 1 1 d . . . . .
C14 C 0.8664(3) 0.4018(3) 0.41532(15) 0.0217(4) Uani 1 1 d . . . . .
H14 H 0.929604 0.353541 0.359643 0.026 Uiso 1 1 calc R U . . .
C15 C 0.7477(3) 0.5552(2) 0.38859(15) 0.0215(4) Uani 1 1 d . . . . .
H15 H 0.729218 0.614618 0.314332 0.026 Uiso 1 1 calc R U . . .
C16 C 0.6552(2) 0.6222(2) 0.47173(15) 0.0182(4) Uani 1 1 d . . . . .
C17 C 0.6800(2) 0.5400(2) 0.58037(14) 0.0156(4) Uani 1 1 d . . . . .
H17 H 0.614072 0.588002 0.635363 0.019 Uiso 1 1 calc R U . . .
C18 C 0.8032(2) 0.3848(2) 0.60961(14) 0.0149(3) Uani 1 1 d . . . . .


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

_exptl_special_details           
; 
One distinct cell was identified using APEX4 (Bruker, 2016).  Thirteen 
frame series were integrated and filtered for statistical outliers using 
SAINT (Bruker, 2016) then corrected for absorption by integration using 
SAINT/SADABS v2014/2 (Bruker, 2016) to sort, merge, and scale the combined 
data.  No decay correction was applied.    
;

loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0.00 -1.00 0.00 0.0440
0.00 1.00 0.00 0.0520
-1.00 -1.00 -1.00 0.0170
-1.00 -1.00 0.00 0.0230
1.00 1.00 0.00 0.0440
0.00 0.00 -1.00 0.0140
0.00 0.00 1.00 0.0240

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
Br1 C16 1.8953(19) . ?
F1 C2 1.4029(19) . ?
O1 C1 1.208(2) . ?
O2 C12 1.360(2) . ?
O2 C13 1.379(2) . ?
O3 C12 1.200(2) . ?
O4 N2 1.222(2) . ?
O5 N2 1.223(2) . ?
N1 C1 1.364(2) . ?
N1 C8 1.410(2) . ?
N1 C9 1.457(2) . ?
N2 C11 1.476(2) . ?
C1 C2 1.565(2) . ?
C2 C3 1.504(2) . ?
C2 C10 1.520(2) . ?
C3 C4 1.382(3) . ?
C3 C8 1.394(2) . ?
C4 C5 1.399(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.388(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.393(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.386(3) . ?
C7 H7 0.9500 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 C11 1.349(2) . ?
C10 C18 1.460(2) . ?
C11 C12 1.470(2) . ?
C13 C14 1.388(3) . ?
C13 C18 1.401(3) . ?
C14 C15 1.378(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.392(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.379(2) . ?
C17 C18 1.407(3) . ?
C17 H17 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
C12 O2 C13 121.98(14) . . ?
C1 N1 C8 111.52(14) . . ?
C1 N1 C9 123.39(15) . . ?
C8 N1 C9 125.09(15) . . ?
O4 N2 O5 125.68(16) . . ?
O4 N2 C11 117.48(15) . . ?
O5 N2 C11 116.69(15) . . ?
O1 C1 N1 127.59(16) . . ?
O1 C1 C2 125.37(15) . . ?
N1 C1 C2 107.00(14) . . ?
F1 C2 C3 110.51(13) . . ?
F1 C2 C10 107.67(13) . . ?
C3 C2 C10 116.58(14) . . ?
F1 C2 C1 104.26(13) . . ?
C3 C2 C1 102.85(14) . . ?
C10 C2 C1 114.28(14) . . ?
C4 C3 C8 121.03(16) . . ?
C4 C3 C2 130.79(16) . . ?
C8 C3 C2 108.05(15) . . ?
C3 C4 C5 117.90(17) . . ?
C3 C4 H4 121.0 . . ?
C5 C4 H4 121.0 . . ?
C6 C5 C4 120.34(17) . . ?
C6 C5 H5 119.8 . . ?
C4 C5 H5 119.8 . . ?
C5 C6 C7 122.18(17) . . ?
C5 C6 H6 118.9 . . ?
C7 C6 H6 118.9 . . ?
C8 C7 C6 116.69(17) . . ?
C8 C7 H7 121.7 . . ?
C6 C7 H7 121.7 . . ?
C7 C8 C3 121.83(17) . . ?
C7 C8 N1 127.59(16) . . ?
C3 C8 N1 110.55(15) . . ?
N1 C9 H9A 109.5 . . ?
N1 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
N1 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C11 C10 C18 116.36(16) . . ?
C11 C10 C2 122.09(16) . . ?
C18 C10 C2 121.55(15) . . ?
C10 C11 C12 125.24(17) . . ?
C10 C11 N2 124.30(16) . . ?
C12 C11 N2 110.46(15) . . ?
O3 C12 O2 119.79(17) . . ?
O3 C12 C11 124.79(18) . . ?
O2 C12 C11 115.41(16) . . ?
O2 C13 C14 115.16(16) . . ?
O2 C13 C18 122.28(16) . . ?
C14 C13 C18 122.56(18) . . ?
C15 C14 C13 119.23(17) . . ?
C15 C14 H14 120.4 . . ?
C13 C14 H14 120.4 . . ?
C14 C15 C16 119.21(17) . . ?
C14 C15 H15 120.4 . . ?
C16 C15 H15 120.4 . . ?
C17 C16 C15 121.87(18) . . ?
C17 C16 Br1 118.62(14) . . ?
C15 C16 Br1 119.51(14) . . ?
C16 C17 C18 119.87(17) . . ?
C16 C17 H17 120.1 . . ?
C18 C17 H17 120.1 . . ?
C13 C18 C17 117.24(16) . . ?
C13 C18 C10 118.39(16) . . ?
C17 C18 C10 124.36(16) . . ?

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
C8 N1 C1 O1 -177.29(16) . . . . ?
C9 N1 C1 O1 2.9(3) . . . . ?
C8 N1 C1 C2 0.53(18) . . . . ?
C9 N1 C1 C2 -179.29(15) . . . . ?
O1 C1 C2 F1 63.1(2) . . . . ?
N1 C1 C2 F1 -114.83(14) . . . . ?
O1 C1 C2 C3 178.45(16) . . . . ?
N1 C1 C2 C3 0.56(17) . . . . ?
O1 C1 C2 C10 -54.2(2) . . . . ?
N1 C1 C2 C10 127.90(15) . . . . ?
F1 C2 C3 C4 -66.4(2) . . . . ?
C10 C2 C3 C4 57.0(2) . . . . ?
C1 C2 C3 C4 -177.19(17) . . . . ?
F1 C2 C3 C8 109.34(15) . . . . ?
C10 C2 C3 C8 -127.32(16) . . . . ?
C1 C2 C3 C8 -1.45(17) . . . . ?
C8 C3 C4 C5 -0.8(3) . . . . ?
C2 C3 C4 C5 174.48(17) . . . . ?
C3 C4 C5 C6 1.2(3) . . . . ?
C4 C5 C6 C7 -0.4(3) . . . . ?
C5 C6 C7 C8 -0.8(3) . . . . ?
C6 C7 C8 C3 1.3(3) . . . . ?
C6 C7 C8 N1 -177.05(16) . . . . ?
C4 C3 C8 C7 -0.5(3) . . . . ?
C2 C3 C8 C7 -176.69(15) . . . . ?
C4 C3 C8 N1 178.10(15) . . . . ?
C2 C3 C8 N1 1.87(19) . . . . ?
C1 N1 C8 C7 176.92(17) . . . . ?
C9 N1 C8 C7 -3.3(3) . . . . ?
C1 N1 C8 C3 -1.55(19) . . . . ?
C9 N1 C8 C3 178.27(15) . . . . ?
F1 C2 C10 C11 23.6(2) . . . . ?
C3 C2 C10 C11 -101.2(2) . . . . ?
C1 C2 C10 C11 138.89(17) . . . . ?
F1 C2 C10 C18 -156.40(15) . . . . ?
C3 C2 C10 C18 78.8(2) . . . . ?
C1 C2 C10 C18 -41.1(2) . . . . ?
C18 C10 C11 C12 4.5(3) . . . . ?
C2 C10 C11 C12 -175.53(16) . . . . ?
C18 C10 C11 N2 -174.76(15) . . . . ?
C2 C10 C11 N2 5.2(3) . . . . ?
O4 N2 C11 C10 -108.8(2) . . . . ?
O5 N2 C11 C10 75.4(2) . . . . ?
O4 N2 C11 C12 71.87(19) . . . . ?
O5 N2 C11 C12 -103.97(18) . . . . ?
C13 O2 C12 O3 176.00(17) . . . . ?
C13 O2 C12 C11 -5.1(2) . . . . ?
C10 C11 C12 O3 179.43(18) . . . . ?
N2 C11 C12 O3 -1.3(3) . . . . ?
C10 C11 C12 O2 0.6(3) . . . . ?
N2 C11 C12 O2 179.89(14) . . . . ?
C12 O2 C13 C14 -175.15(16) . . . . ?
C12 O2 C13 C18 4.4(3) . . . . ?
O2 C13 C14 C15 179.25(16) . . . . ?
C18 C13 C14 C15 -0.3(3) . . . . ?
C13 C14 C15 C16 -0.8(3) . . . . ?
C14 C15 C16 C17 0.6(3) . . . . ?
C14 C15 C16 Br1 -179.97(14) . . . . ?
C15 C16 C17 C18 0.8(3) . . . . ?
Br1 C16 C17 C18 -178.67(13) . . . . ?
O2 C13 C18 C17 -177.91(15) . . . . ?
C14 C13 C18 C17 1.6(3) . . . . ?
O2 C13 C18 C10 1.1(3) . . . . ?
C14 C13 C18 C10 -179.45(16) . . . . ?
C16 C17 C18 C13 -1.8(2) . . . . ?
C16 C17 C18 C10 179.29(16) . . . . ?
C11 C10 C18 C13 -5.2(2) . . . . ?
C2 C10 C18 C13 174.82(15) . . . . ?
C11 C10 C18 C17 173.73(17) . . . . ?
C2 C10 C18 C17 -6.3(3) . . . . ?

_refine_diff_density_max         0.399
_refine_diff_density_min         -0.298
_refine_diff_density_rms         0.056



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

data_B25039_a
_database_code_depnum_ccdc_archive 'CCDC 2426005'
loop_
_audit_author_name
_audit_author_address
'Jeffery A. Bertke'
;Georgetown University
United States of America
;
_audit_update_record             
;
2025-02-21 deposited with the CCDC.	2025-04-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/1
_shelx_SHELXL_version_number     2019/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H10 Cl F N2 O5'
_chemical_formula_sum            'C18 H10 Cl F N2 O5'
_chemical_formula_weight         388.73

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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'

_cell_length_a                   9.7610(2)
_cell_length_b                   10.0249(2)
_cell_length_c                   17.7207(4)
_cell_angle_alpha                90
_cell_angle_beta                 104.6830(10)
_cell_angle_gamma                90
_cell_volume                     1677.40(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9289
_cell_measurement_theta_min      2.78
_cell_measurement_theta_max      30.46
_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.539
_exptl_crystal_F_000             792
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.314
_exptl_crystal_size_mid          0.111
_exptl_crystal_size_min          0.107
_exptl_absorpt_coefficient_mu    0.273
_shelx_estimated_absorpt_T_min   0.919
_shelx_estimated_absorpt_T_max   0.971
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.95979
_exptl_absorpt_correction_T_max  0.98870
_exptl_absorpt_process_details   'SADABS V2016/2 (Bruker, 2016)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'microfocus sealed tube'
_diffrn_radiation_monochromator  'multilayer mirrors'
_diffrn_measurement_device_type  'Bruker D8 Quest/Photon 3'
_diffrn_measurement_method       'profile data from φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            73034
_diffrn_reflns_av_unetI/netI     0.0284
_diffrn_reflns_av_R_equivalents  0.0389
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         2.714
_diffrn_reflns_theta_max         30.536
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             10217
_reflns_number_gt                9793
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.898
_reflns_Friedel_fraction_max     0.996
_reflns_Friedel_fraction_full    0.995

_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       'APEX4 V2016.5-0 (Bruker, 2016)'
_computing_cell_refinement       'SAINT V8.37A (Bruker, 2005)'
_computing_data_reduction        
; 
SAINT V8.37A, XPREP v2014/2, SADABS V2016/2 (Bruker, 2016) 
;
_computing_structure_solution    'SHELX-2014-5 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2019)'
_computing_molecular_graphics    'SHELXLE v932 (Hubschle, 2011)'
_computing_publication_material  'XCIF V2014-2 (Bruker, 2014)'

_refine_special_details          
; 
Structure was phased by intrinsic methods (Sheldrick, 2015).  Systematic 
conditions suggested the ambiguous space group.  The space group choice was 
confirmed by successful convergence of the full-matrix least-squares 
refinement on F².  The final map had no significant features.  A final 
analysis of variance between observed and calculated structure factors 
showed little dependence on amplitude and resolution. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0521P)²+0.3044P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     intrinsic
_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_abs_structure_details 
;
 Flack x determined using 4459 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.018(13)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         10217
_refine_ls_number_parameters     489
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0345
_refine_ls_R_factor_gt           0.0328
_refine_ls_wR_factor_ref         0.0863
_refine_ls_wR_factor_gt          0.0850
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_restrained_S_all      1.035
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.64635(6) 0.60902(6) 0.69899(3) 0.03275(12) Uani 1 1 d . . . . .
Cl2 Cl 1.06716(5) 0.39960(5) 1.20493(3) 0.02513(10) Uani 1 1 d . . . . .
F1 F 1.04710(12) 0.42379(12) 0.47247(7) 0.0238(2) Uani 1 1 d . . . . .
F2 F 0.45269(11) 0.56463(12) 0.98855(7) 0.0223(2) Uani 1 1 d . . . . .
O1 O 0.81343(16) 0.38001(15) 0.33470(8) 0.0264(3) Uani 1 1 d . . . . .
O2 O 1.07481(16) 0.83118(15) 0.31584(9) 0.0282(3) Uani 1 1 d . . . . .
O3 O 1.29121(18) 0.74428(18) 0.34434(10) 0.0355(4) Uani 1 1 d . . . . .
O4 O 1.25345(18) 0.44831(19) 0.38441(11) 0.0370(4) Uani 1 1 d . . . . .
O5 O 1.30496(17) 0.5604(2) 0.49317(11) 0.0396(4) Uani 1 1 d . . . . .
O6 O 0.54194(14) 0.61271(15) 0.84643(8) 0.0227(3) Uani 1 1 d . . . . .
O7 O 0.26184(14) 0.16501(14) 0.82928(8) 0.0219(3) Uani 1 1 d . . . . .
O8 O 0.07713(15) 0.25447(16) 0.86200(10) 0.0294(3) Uani 1 1 d . . . . .
O9 O 0.16319(18) 0.54411(18) 0.91150(13) 0.0439(5) Uani 1 1 d . . . . .
O10 O 0.2207(2) 0.4237(2) 1.01733(12) 0.0451(5) Uani 1 1 d . . . . .
N1 N 0.71163(17) 0.42322(17) 0.43642(9) 0.0218(3) Uani 1 1 d . . . . .
N2 N 1.23365(18) 0.5385(2) 0.42697(12) 0.0287(4) Uani 1 1 d . . . . .
N3 N 0.74565(16) 0.56618(16) 0.94239(9) 0.0188(3) Uani 1 1 d . . . . .
N4 N 0.22311(19) 0.45050(19) 0.95045(13) 0.0308(4) Uani 1 1 d . . . . .
C1 C 0.81303(19) 0.43201(18) 0.39628(11) 0.0200(3) Uani 1 1 d . . . . .
C2 C 0.93731(19) 0.51632(18) 0.44763(10) 0.0186(3) Uani 1 1 d . . . . .
C3 C 0.88060(18) 0.55612(18) 0.51513(10) 0.0183(3) Uani 1 1 d . . . . .
C4 C 0.9406(2) 0.63356(19) 0.57942(11) 0.0216(3) Uani 1 1 d . . . . .
H4 H 1.030802 0.673773 0.585119 0.026 Uiso 1 1 calc R U . . .
C5 C 0.8652(2) 0.6510(2) 0.63571(11) 0.0248(4) Uani 1 1 d . . . . .
H5 H 0.903558 0.703794 0.680629 0.030 Uiso 1 1 calc R U . . .
C6 C 0.7338(2) 0.5911(2) 0.62590(11) 0.0240(4) Uani 1 1 d . . . . .
C7 C 0.6701(2) 0.5133(2) 0.56081(11) 0.0230(4) Uani 1 1 d . . . . .
H7 H 0.579096 0.474467 0.554363 0.028 Uiso 1 1 calc R U . . .
C8 C 0.7487(2) 0.49683(18) 0.50655(11) 0.0196(3) Uani 1 1 d . . . . .
C9 C 0.5816(2) 0.3465(2) 0.40919(14) 0.0308(4) Uani 1 1 d . . . . .
H9A H 0.570403 0.285669 0.450508 0.046 Uiso 1 1 calc R U . . .
H9B H 0.586341 0.294865 0.362975 0.046 Uiso 1 1 calc R U . . .
H9C H 0.500495 0.407452 0.395785 0.046 Uiso 1 1 calc R U . . .
C10 C 0.9865(2) 0.62694(18) 0.40295(10) 0.0194(3) Uani 1 1 d . . . . .
C11 C 1.1194(2) 0.6339(2) 0.39400(11) 0.0226(3) Uani 1 1 d . . . . .
C12 C 1.1716(2) 0.7378(2) 0.35050(12) 0.0267(4) Uani 1 1 d . . . . .
C13 C 0.9382(2) 0.8308(2) 0.32388(11) 0.0237(4) Uani 1 1 d . . . . .
C14 C 0.8523(2) 0.9339(2) 0.28637(12) 0.0288(4) Uani 1 1 d . . . . .
H14 H 0.888297 0.998603 0.257243 0.035 Uiso 1 1 calc R U . . .
C15 C 0.7144(3) 0.9412(2) 0.29191(12) 0.0304(4) Uani 1 1 d . . . . .
H15 H 0.655007 1.011580 0.266607 0.036 Uiso 1 1 calc R U . . .
C16 C 0.6610(2) 0.8460(2) 0.33444(12) 0.0271(4) Uani 1 1 d . . . . .
H16 H 0.565836 0.851748 0.338247 0.032 Uiso 1 1 calc R U . . .
C17 C 0.7474(2) 0.7430(2) 0.37109(11) 0.0232(4) Uani 1 1 d . . . . .
H17 H 0.710479 0.678336 0.399791 0.028 Uiso 1 1 calc R U . . .
C18 C 0.8888(2) 0.73258(18) 0.36658(10) 0.0204(3) Uani 1 1 d . . . . .
C19 C 0.60508(19) 0.55852(18) 0.90602(10) 0.0182(3) Uani 1 1 d . . . . .
C20 C 0.53431(18) 0.47232(18) 0.95913(10) 0.0170(3) Uani 1 1 d . . . . .
C21 C 0.65738(19) 0.42924(17) 1.02368(10) 0.0176(3) Uani 1 1 d . . . . .
C22 C 0.6630(2) 0.35240(18) 1.08889(11) 0.0201(3) Uani 1 1 d . . . . .
H22 H 0.580863 0.308199 1.095704 0.024 Uiso 1 1 calc R U . . .
C23 C 0.7921(2) 0.34105(19) 1.14465(10) 0.0211(3) Uani 1 1 d . . . . .
H23 H 0.798808 0.290322 1.190728 0.025 Uiso 1 1 calc R U . . .
C24 C 0.91066(19) 0.40470(18) 1.13207(10) 0.0189(3) Uani 1 1 d . . . . .
C25 C 0.90937(19) 0.47864(18) 1.06483(10) 0.0188(3) Uani 1 1 d . . . . .
H25 H 0.992735 0.517596 1.056103 0.023 Uiso 1 1 calc R U . . .
C26 C 0.77902(19) 0.49118(17) 1.01208(10) 0.0174(3) Uani 1 1 d . . . . .
C27 C 0.8476(2) 0.6405(2) 0.91153(12) 0.0267(4) Uani 1 1 d . . . . .
H27A H 0.907831 0.694078 0.953248 0.040 Uiso 1 1 calc R U . . .
H27B H 0.797129 0.699310 0.869473 0.040 Uiso 1 1 calc R U . . .
H27C H 0.906618 0.577971 0.891104 0.040 Uiso 1 1 calc R U . . .
C28 C 0.43888(19) 0.36445(17) 0.91497(10) 0.0174(3) Uani 1 1 d . . . . .
C29 C 0.2995(2) 0.35719(19) 0.91154(11) 0.0209(3) Uani 1 1 d . . . . .
C30 C 0.2026(2) 0.2577(2) 0.86678(11) 0.0226(3) Uani 1 1 d . . . . .
C31 C 0.40432(19) 0.16610(18) 0.83175(10) 0.0187(3) Uani 1 1 d . . . . .
C32 C 0.4495(2) 0.0638(2) 0.79056(11) 0.0233(4) Uani 1 1 d . . . . .
H32 H 0.384712 -0.001638 0.763803 0.028 Uiso 1 1 calc R U . . .
C33 C 0.5903(2) 0.0595(2) 0.78946(11) 0.0264(4) Uani 1 1 d . . . . .
H33 H 0.622758 -0.009394 0.761536 0.032 Uiso 1 1 calc R U . . .
C34 C 0.6854(2) 0.1554(2) 0.82894(11) 0.0244(4) Uani 1 1 d . . . . .
H34 H 0.781983 0.152018 0.827506 0.029 Uiso 1 1 calc R U . . .
C35 C 0.6389(2) 0.2555(2) 0.87017(11) 0.0210(3) Uani 1 1 d . . . . .
H35 H 0.704415 0.320078 0.897191 0.025 Uiso 1 1 calc R U . . .
C36 C 0.49619(19) 0.26306(18) 0.87274(10) 0.0177(3) Uani 1 1 d . . . . .


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

_exptl_special_details           
; 
One distinct cell was identified using APEX4 (Bruker, 2016).  Ten frame 
series were integrated and filtered for statistical outliers using SAINT 
(Bruker, 2016) then corrected for absorption by integration using 
SAINT/SADABS v2014/2 (Bruker, 2016) to sort, merge, and scale the combined 
data.  No decay correction was applied.    
;

loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-2.00 2.00 -1.00 0.1320
-1.00 0.00 -1.00 0.1440
-1.00 0.00 0.00 0.1600
-1.00 0.00 1.00 0.1410
0.00 1.00 1.00 0.0510
0.00 -1.00 -1.00 0.0530
0.00 0.00 1.00 0.0310
0.00 0.00 -1.00 0.0520
0.00 1.00 -2.00 0.0530
0.00 -1.00 2.00 0.0480
1.00 0.00 -1.00 0.1180
1.00 0.00 0.00 0.1260

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 C6 1.7320(19) . ?
Cl2 C24 1.7330(18) . ?
F1 C2 1.401(2) . ?
F2 C20 1.4048(19) . ?
O1 C1 1.210(2) . ?
O2 C12 1.361(3) . ?
O2 C13 1.377(3) . ?
O3 C12 1.201(3) . ?
O4 N2 1.223(3) . ?
O5 N2 1.223(3) . ?
O6 C19 1.208(2) . ?
O7 C30 1.354(2) . ?
O7 C31 1.380(2) . ?
O8 C30 1.207(2) . ?
O9 N4 1.223(3) . ?
O10 N4 1.221(3) . ?
N1 C1 1.360(2) . ?
N1 C8 1.411(2) . ?
N1 C9 1.458(2) . ?
N2 C11 1.473(3) . ?
N3 C19 1.362(2) . ?
N3 C26 1.412(2) . ?
N3 C27 1.456(2) . ?
N4 C29 1.472(3) . ?
C1 C2 1.567(3) . ?
C2 C3 1.494(2) . ?
C2 C10 1.510(3) . ?
C3 C4 1.380(3) . ?
C3 C8 1.391(3) . ?
C4 C5 1.393(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.386(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.400(3) . ?
C7 C8 1.383(3) . ?
C7 H7 0.9500 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 C11 1.349(3) . ?
C10 C18 1.461(3) . ?
C11 C12 1.462(3) . ?
C13 C14 1.390(3) . ?
C13 C18 1.400(3) . ?
C14 C15 1.376(4) . ?
C14 H14 0.9500 . ?
C15 C16 1.396(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.386(3) . ?
C16 H16 0.9500 . ?
C17 C18 1.406(3) . ?
C17 H17 0.9500 . ?
C19 C20 1.562(2) . ?
C20 C21 1.497(2) . ?
C20 C28 1.510(2) . ?
C21 C22 1.378(2) . ?
C21 C26 1.401(2) . ?
C22 C23 1.395(3) . ?
C22 H22 0.9500 . ?
C23 C24 1.388(3) . ?
C23 H23 0.9500 . ?
C24 C25 1.401(2) . ?
C25 C26 1.380(3) . ?
C25 H25 0.9500 . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
C28 C29 1.348(2) . ?
C28 C36 1.456(2) . ?
C29 C30 1.462(3) . ?
C31 C32 1.394(3) . ?
C31 C36 1.395(3) . ?
C32 C33 1.380(3) . ?
C32 H32 0.9500 . ?
C33 C34 1.395(3) . ?
C33 H33 0.9500 . ?
C34 C35 1.383(3) . ?
C34 H34 0.9500 . ?
C35 C36 1.408(3) . ?
C35 H35 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
C12 O2 C13 122.09(16) . . ?
C30 O7 C31 122.06(15) . . ?
C1 N1 C8 111.64(15) . . ?
C1 N1 C9 123.30(17) . . ?
C8 N1 C9 125.06(17) . . ?
O5 N2 O4 125.7(2) . . ?
O5 N2 C11 116.98(18) . . ?
O4 N2 C11 117.21(18) . . ?
C19 N3 C26 111.43(15) . . ?
C19 N3 C27 123.61(16) . . ?
C26 N3 C27 124.94(15) . . ?
O10 N4 O9 126.3(2) . . ?
O10 N4 C29 116.9(2) . . ?
O9 N4 C29 116.7(2) . . ?
O1 C1 N1 127.79(18) . . ?
O1 C1 C2 125.25(17) . . ?
N1 C1 C2 106.86(15) . . ?
F1 C2 C3 109.53(14) . . ?
F1 C2 C10 109.37(14) . . ?
C3 C2 C10 117.08(15) . . ?
F1 C2 C1 104.08(14) . . ?
C3 C2 C1 102.69(14) . . ?
C10 C2 C1 113.19(15) . . ?
C4 C3 C8 121.19(17) . . ?
C4 C3 C2 130.17(17) . . ?
C8 C3 C2 108.60(15) . . ?
C3 C4 C5 118.09(18) . . ?
C3 C4 H4 121.0 . . ?
C5 C4 H4 121.0 . . ?
C6 C5 C4 119.71(18) . . ?
C6 C5 H5 120.1 . . ?
C4 C5 H5 120.1 . . ?
C5 C6 C7 123.24(17) . . ?
C5 C6 Cl1 118.47(15) . . ?
C7 C6 Cl1 118.26(16) . . ?
C8 C7 C6 115.48(18) . . ?
C8 C7 H7 122.3 . . ?
C6 C7 H7 122.3 . . ?
C7 C8 C3 122.27(18) . . ?
C7 C8 N1 127.67(18) . . ?
C3 C8 N1 110.06(16) . . ?
N1 C9 H9A 109.5 . . ?
N1 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
N1 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C11 C10 C18 116.78(17) . . ?
C11 C10 C2 122.87(17) . . ?
C18 C10 C2 120.35(16) . . ?
C10 C11 C12 124.97(19) . . ?
C10 C11 N2 125.04(18) . . ?
C12 C11 N2 109.99(17) . . ?
O3 C12 O2 120.1(2) . . ?
O3 C12 C11 124.3(2) . . ?
O2 C12 C11 115.67(18) . . ?
O2 C13 C14 115.55(18) . . ?
O2 C13 C18 122.21(18) . . ?
C14 C13 C18 122.2(2) . . ?
C15 C14 C13 119.2(2) . . ?
C15 C14 H14 120.4 . . ?
C13 C14 H14 120.4 . . ?
C14 C15 C16 120.5(2) . . ?
C14 C15 H15 119.7 . . ?
C16 C15 H15 119.7 . . ?
C17 C16 C15 119.7(2) . . ?
C17 C16 H16 120.1 . . ?
C15 C16 H16 120.1 . . ?
C16 C17 C18 121.23(19) . . ?
C16 C17 H17 119.4 . . ?
C18 C17 H17 119.4 . . ?
C13 C18 C17 117.09(18) . . ?
C13 C18 C10 118.23(18) . . ?
C17 C18 C10 124.68(17) . . ?
O6 C19 N3 128.14(17) . . ?
O6 C19 C20 124.74(16) . . ?
N3 C19 C20 107.00(15) . . ?
F2 C20 C21 109.10(14) . . ?
F2 C20 C28 109.31(14) . . ?
C21 C20 C28 117.36(15) . . ?
F2 C20 C19 103.78(14) . . ?
C21 C20 C19 103.20(14) . . ?
C28 C20 C19 113.14(14) . . ?
C22 C21 C26 121.06(17) . . ?
C22 C21 C20 130.95(16) . . ?
C26 C21 C20 107.81(15) . . ?
C21 C22 C23 118.43(17) . . ?
C21 C22 H22 120.8 . . ?
C23 C22 H22 120.8 . . ?
C24 C23 C22 119.27(17) . . ?
C24 C23 H23 120.4 . . ?
C22 C23 H23 120.4 . . ?
C23 C24 C25 123.49(17) . . ?
C23 C24 Cl2 118.69(14) . . ?
C25 C24 Cl2 117.75(14) . . ?
C26 C25 C24 115.61(16) . . ?
C26 C25 H25 122.2 . . ?
C24 C25 H25 122.2 . . ?
C25 C26 C21 122.03(16) . . ?
C25 C26 N3 127.57(16) . . ?
C21 C26 N3 110.39(15) . . ?
N3 C27 H27A 109.5 . . ?
N3 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
N3 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C29 C28 C36 117.00(16) . . ?
C29 C28 C20 123.02(16) . . ?
C36 C28 C20 119.97(15) . . ?
C28 C29 C30 124.59(17) . . ?
C28 C29 N4 124.74(17) . . ?
C30 C29 N4 110.65(16) . . ?
O8 C30 O7 119.93(18) . . ?
O8 C30 C29 124.18(19) . . ?
O7 C30 C29 115.89(16) . . ?
O7 C31 C32 115.30(16) . . ?
O7 C31 C36 122.10(16) . . ?
C32 C31 C36 122.59(17) . . ?
C33 C32 C31 118.57(18) . . ?
C33 C32 H32 120.7 . . ?
C31 C32 H32 120.7 . . ?
C32 C33 C34 120.69(18) . . ?
C32 C33 H33 119.7 . . ?
C34 C33 H33 119.7 . . ?
C35 C34 C33 119.91(18) . . ?
C35 C34 H34 120.0 . . ?
C33 C34 H34 120.0 . . ?
C34 C35 C36 121.08(18) . . ?
C34 C35 H35 119.5 . . ?
C36 C35 H35 119.5 . . ?
C31 C36 C35 117.15(16) . . ?
C31 C36 C28 118.31(16) . . ?
C35 C36 C28 124.55(16) . . ?

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
C8 N1 C1 O1 179.50(19) . . . . ?
C9 N1 C1 O1 -0.5(3) . . . . ?
C8 N1 C1 C2 3.1(2) . . . . ?
C9 N1 C1 C2 -176.90(17) . . . . ?
O1 C1 C2 F1 -66.2(2) . . . . ?
N1 C1 C2 F1 110.31(16) . . . . ?
O1 C1 C2 C3 179.57(18) . . . . ?
N1 C1 C2 C3 -3.88(19) . . . . ?
O1 C1 C2 C10 52.4(2) . . . . ?
N1 C1 C2 C10 -131.04(16) . . . . ?
F1 C2 C3 C4 71.1(2) . . . . ?
C10 C2 C3 C4 -54.1(3) . . . . ?
C1 C2 C3 C4 -178.78(18) . . . . ?
F1 C2 C3 C8 -106.78(17) . . . . ?
C10 C2 C3 C8 128.01(17) . . . . ?
C1 C2 C3 C8 3.37(19) . . . . ?
C8 C3 C4 C5 -0.1(3) . . . . ?
C2 C3 C4 C5 -177.72(18) . . . . ?
C3 C4 C5 C6 0.0(3) . . . . ?
C4 C5 C6 C7 -0.7(3) . . . . ?
C4 C5 C6 Cl1 177.29(15) . . . . ?
C5 C6 C7 C8 1.4(3) . . . . ?
Cl1 C6 C7 C8 -176.62(14) . . . . ?
C6 C7 C8 C3 -1.5(3) . . . . ?
C6 C7 C8 N1 179.39(18) . . . . ?
C4 C3 C8 C7 0.9(3) . . . . ?
C2 C3 C8 C7 178.94(17) . . . . ?
C4 C3 C8 N1 -179.86(16) . . . . ?
C2 C3 C8 N1 -1.8(2) . . . . ?
C1 N1 C8 C7 178.30(19) . . . . ?
C9 N1 C8 C7 -1.7(3) . . . . ?
C1 N1 C8 C3 -0.9(2) . . . . ?
C9 N1 C8 C3 179.04(18) . . . . ?
F1 C2 C10 C11 -3.3(2) . . . . ?
C3 C2 C10 C11 122.00(19) . . . . ?
C1 C2 C10 C11 -118.83(19) . . . . ?
F1 C2 C10 C18 176.36(15) . . . . ?
C3 C2 C10 C18 -58.3(2) . . . . ?
C1 C2 C10 C18 60.8(2) . . . . ?
C18 C10 C11 C12 -0.5(3) . . . . ?
C2 C10 C11 C12 179.15(17) . . . . ?
C18 C10 C11 N2 179.10(17) . . . . ?
C2 C10 C11 N2 -1.2(3) . . . . ?
O5 N2 C11 C10 -87.4(3) . . . . ?
O4 N2 C11 C10 96.2(2) . . . . ?
O5 N2 C11 C12 92.3(2) . . . . ?
O4 N2 C11 C12 -84.1(2) . . . . ?
C13 O2 C12 O3 -177.35(19) . . . . ?
C13 O2 C12 C11 2.5(3) . . . . ?
C10 C11 C12 O3 178.4(2) . . . . ?
N2 C11 C12 O3 -1.3(3) . . . . ?
C10 C11 C12 O2 -1.5(3) . . . . ?
N2 C11 C12 O2 178.87(16) . . . . ?
C12 O2 C13 C14 178.80(17) . . . . ?
C12 O2 C13 C18 -1.6(3) . . . . ?
O2 C13 C14 C15 -179.62(17) . . . . ?
C18 C13 C14 C15 0.8(3) . . . . ?
C13 C14 C15 C16 -0.2(3) . . . . ?
C14 C15 C16 C17 -0.3(3) . . . . ?
C15 C16 C17 C18 0.2(3) . . . . ?
O2 C13 C18 C17 179.63(17) . . . . ?
C14 C13 C18 C17 -0.8(3) . . . . ?
O2 C13 C18 C10 -0.5(3) . . . . ?
C14 C13 C18 C10 179.04(17) . . . . ?
C16 C17 C18 C13 0.3(3) . . . . ?
C16 C17 C18 C10 -179.55(18) . . . . ?
C11 C10 C18 C13 1.5(2) . . . . ?
C2 C10 C18 C13 -178.18(16) . . . . ?
C11 C10 C18 C17 -178.67(17) . . . . ?
C2 C10 C18 C17 1.7(3) . . . . ?
C26 N3 C19 O6 178.44(18) . . . . ?
C27 N3 C19 O6 -2.8(3) . . . . ?
C26 N3 C19 C20 2.32(19) . . . . ?
C27 N3 C19 C20 -178.94(17) . . . . ?
O6 C19 C20 F2 -66.4(2) . . . . ?
N3 C19 C20 F2 109.87(15) . . . . ?
O6 C19 C20 C21 179.78(17) . . . . ?
N3 C19 C20 C21 -3.93(18) . . . . ?
O6 C19 C20 C28 51.9(2) . . . . ?
N3 C19 C20 C28 -131.77(16) . . . . ?
F2 C20 C21 C22 69.4(2) . . . . ?
C28 C20 C21 C22 -55.6(2) . . . . ?
C19 C20 C21 C22 179.23(18) . . . . ?
F2 C20 C21 C26 -105.73(16) . . . . ?
C28 C20 C21 C26 129.30(16) . . . . ?
C19 C20 C21 C26 4.15(18) . . . . ?
C26 C21 C22 C23 2.1(3) . . . . ?
C20 C21 C22 C23 -172.48(17) . . . . ?
C21 C22 C23 C24 -1.3(3) . . . . ?
C22 C23 C24 C25 -1.4(3) . . . . ?
C22 C23 C24 Cl2 175.44(14) . . . . ?
C23 C24 C25 C26 3.3(3) . . . . ?
Cl2 C24 C25 C26 -173.58(13) . . . . ?
C24 C25 C26 C21 -2.6(3) . . . . ?
C24 C25 C26 N3 175.87(17) . . . . ?
C22 C21 C26 C25 0.0(3) . . . . ?
C20 C21 C26 C25 175.63(16) . . . . ?
C22 C21 C26 N3 -178.72(16) . . . . ?
C20 C21 C26 N3 -3.05(19) . . . . ?
C19 N3 C26 C25 -178.20(17) . . . . ?
C27 N3 C26 C25 3.1(3) . . . . ?
C19 N3 C26 C21 0.4(2) . . . . ?
C27 N3 C26 C21 -178.33(18) . . . . ?
F2 C20 C28 C29 -4.8(2) . . . . ?
C21 C20 C28 C29 120.10(19) . . . . ?
C19 C20 C28 C29 -119.86(19) . . . . ?
F2 C20 C28 C36 174.44(14) . . . . ?
C21 C20 C28 C36 -60.7(2) . . . . ?
C19 C20 C28 C36 59.3(2) . . . . ?
C36 C28 C29 C30 -1.9(3) . . . . ?
C20 C28 C29 C30 177.31(17) . . . . ?
C36 C28 C29 N4 179.93(18) . . . . ?
C20 C28 C29 N4 -0.8(3) . . . . ?
O10 N4 C29 C28 -88.3(2) . . . . ?
O9 N4 C29 C28 94.7(2) . . . . ?
O10 N4 C29 C30 93.3(2) . . . . ?
O9 N4 C29 C30 -83.6(2) . . . . ?
C31 O7 C30 O8 178.72(17) . . . . ?
C31 O7 C30 C29 -1.4(2) . . . . ?
C28 C29 C30 O8 -177.53(19) . . . . ?
N4 C29 C30 O8 0.8(3) . . . . ?
C28 C29 C30 O7 2.6(3) . . . . ?
N4 C29 C30 O7 -179.04(16) . . . . ?
C30 O7 C31 C32 179.70(16) . . . . ?
C30 O7 C31 C36 -0.3(2) . . . . ?
O7 C31 C32 C33 179.09(17) . . . . ?
C36 C31 C32 C33 -0.9(3) . . . . ?
C31 C32 C33 C34 0.2(3) . . . . ?
C32 C33 C34 C35 0.5(3) . . . . ?
C33 C34 C35 C36 -0.4(3) . . . . ?
O7 C31 C36 C35 -179.04(16) . . . . ?
C32 C31 C36 C35 1.0(3) . . . . ?
O7 C31 C36 C28 1.0(2) . . . . ?
C32 C31 C36 C28 -178.99(16) . . . . ?
C34 C35 C36 C31 -0.3(3) . . . . ?
C34 C35 C36 C28 179.67(18) . . . . ?
C29 C28 C36 C31 0.1(2) . . . . ?
C20 C28 C36 C31 -179.14(16) . . . . ?
C29 C28 C36 C35 -179.86(18) . . . . ?
C20 C28 C36 C35 0.9(3) . . . . ?

_refine_diff_density_max         0.330
_refine_diff_density_min         -0.240
_refine_diff_density_rms         0.050



