# Supplementary Information (SI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2026

####################################################################### 
# 
# 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_dc707
_database_code_depnum_ccdc_archive 'CCDC 2493076'
loop_
_audit_author_name
_audit_author_address
'Alexander Prado-Roler'
;University of Vienna
Austria
;
_audit_update_record             
;
2025-10-03 deposited with the CCDC.	2026-01-08 downloaded from the CCDC.
;
_audit_creation_date             2025-07-10
_audit_creation_method           
;
Olex2 1.5-alpha
(compiled 2025.07.01 svn.ra095ee60 for OlexSys, GUI svn.r7302)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C9 H9 Br F3 N2 O S'
_chemical_formula_sum            'C9 H8 Br F3 N2 O S'
_chemical_formula_weight         329.14
_chemical_melting_point          ?
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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   8.7339(10)
_cell_length_b                   14.4009(8)
_cell_length_c                   19.2869(13)
_cell_angle_alpha                90
_cell_angle_beta                 102.089(7)
_cell_angle_gamma                90
_cell_volume                     2372.0(3)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    14572
_cell_measurement_temperature    100
_cell_measurement_theta_max      31.22
_cell_measurement_theta_min      2.58
_shelx_estimated_absorpt_T_max   0.930
_shelx_estimated_absorpt_T_min   0.628
_exptl_absorpt_coefficient_mu    3.665
_exptl_absorpt_correction_T_max  0.9290
_exptl_absorpt_correction_T_min  0.5974
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
STOE LANA, absorption correction by scaling of reflection intensities.
J. Koziskova, F. Hahn, J. Richter, J. Kozisek, "Comparison of different
absorption corrections on the model structure of tetrakis(μ₂-acetato)-
diaqua-di-copper(II)", Acta Chimica Slovaca, vol. 9, no. 2, 2016, pp. 136 - 140.
Afterwards a spherical absorption correction was performed within STOE LANA.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_density_diffrn    1.843
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1296
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1399
_diffrn_reflns_av_unetI/netI     0.3041
_diffrn_reflns_Laue_measured_fraction_full 0.979
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            19213
_diffrn_reflns_point_group_measured_fraction_full 0.979
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_theta_full        25.049
_diffrn_reflns_theta_max         25.049
_diffrn_reflns_theta_min         2.863
_diffrn_ambient_temperature      100
_diffrn_detector                 'EIGER2 500K'
_diffrn_detector_area_resol_mean 13.33
_diffrn_measured_fraction_theta_full 0.979
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_details      
;
 3381 frames, detector distance = 50 mm
;
_diffrn_measurement_device       'Eulerian 4-circle diffractometer'
_diffrn_measurement_device_type  'STOE STADIVARI'
_diffrn_measurement_method       'rotation method, ω scans'
_diffrn_radiation_collimation    '1.2 0.6 mm diameter'
_diffrn_radiation_monochromator  'Graded multilayer mirror'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Axo Mo'
_diffrn_source_current           0.830
_diffrn_source_power             0.050
_diffrn_source_voltage           60
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1887
_reflns_number_total             4114
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
X-Area Recipe 2.0.1 (STOE, 2023)
;
_computing_data_collection       
;
X-Area Pilatus3_SV 1.31.192.0 (STOE, 2023)
;
_computing_data_reduction        
;
X-Area Integrate 2.5.15.0 (STOE, 2023)
X-Area X-Red 2.3.1.0 (STOE, 2023)
;
_computing_molecular_graphics    'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         1.213
_refine_diff_density_min         -1.120
_refine_diff_density_rms         0.164
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.963
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     310
_refine_ls_number_reflns         4114
_refine_ls_number_restraints     156
_refine_ls_R_factor_all          0.1709
_refine_ls_R_factor_gt           0.0600
_refine_ls_restrained_S_all      0.953
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0872P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1563
_refine_ls_wR_factor_ref         0.1730
_refine_special_details          
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C8A-C7A
 1.35 with sigma of 0.02
 S1Z-C7Z = S1Z-C6B
 1.71 with sigma of 0.02
 C7Z-C8Z = C9Z-C6B
 1.36 with sigma of 0.02
 S1Y-C7Y = S1Y-C6A
 1.71 with sigma of 0.02
 C8Z-C9Z
 1.42 with sigma of 0.02
 C7Y-C8Y = C9Y-C6A
 1.36 with sigma of 0.02
 C8Y-C9Y
 1.42 with sigma of 0.02
 S1Z-C8Z = S1Z-C9Z
 2.54 with sigma of 0.04
 S1Y-C8Y = S1Y-C9Y
 2.54 with sigma of 0.04
 C7Z-C9Z = C8Z-C6B
 2.31 with sigma of 0.04
 C7Y-C9Y = C8Y-C6A
 2.31 with sigma of 0.04
 S1Y-C8Y ∼ S1Y-C9Y
 with sigma of 0.04
 S1Z-C7Z ∼ S1Z-C6B
 with sigma of 0.02
 C7Z-C8Z ∼ C8Z-C9Z ∼ C9Z-C6B
 with sigma of 0.03
 C7Z-C9Z ∼ C8Z-C6B
 with sigma of 0.04
 S1Z-C8Z ∼ S1Z-C9Z
 with sigma of 0.04
 C7Y-C8Y ∼ C8Y-C9Y ∼ C9Y-C6A
 with sigma of 0.03
 C7Y-C9Y ∼ C8Y-C6A
 with sigma of 0.04
 S1Y-C7Y ∼ S1Y-C6A ∼ S1A-C7A ∼ S1A-C6A
 with sigma of 0.02
 C8B-C7B ∼ C8A-C7A
 with sigma of 0.01
3. Restrained planarity
 S1Y, C6A, C7Y, C8Y, C9Y
 with sigma of 0.1
 S1Z, C6B, C7Z, C8Z, C9Z
 with sigma of 0.1
4. Rigid bond restraints
 C2A, C5A, Br1A
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
5. Uiso/Uaniso restraints and constraints
S1Y ∼ C6A ∼ C7Y ∼ C8Y ∼ C9Y: within 2A with sigma of 0.04 and
sigma for terminal atoms of 0.08 within 2A
S1Z ∼ C6B ∼ C7Z ∼ C8Z ∼ C9Z: within 2A with sigma of 0.04 and
sigma for terminal atoms of 0.08 within 2A
Uanis(S1Z) = Uanis(S1B)
Uanis(C9Z) = Uanis(C8Z) = Uanis(C7B) = Uanis(C7Z) = Uanis(C8B) = Uanis(C9B)
Uanis(C9A) = Uanis(C9Y) = Uanis(C6A)
Uanis(S1Y) = Uanis(S1A)
Uanis(C8A) = Uanis(C7Y) = Uanis(C8Y) = Uanis(C7A)
6. Rigid body (RIGU) restrains
 S1Y, C6A, C7Y, C8Y, C9Y
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 S1Z, C6B, C7Z, C8Z, C9Z
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
7. Others
 Sof(S1Y)=Sof(C7Y)=Sof(H7Y)=Sof(C8Y)=Sof(H8Y)=Sof(C9Y)=Sof(H9Y)=1-FVAR(1)
 Sof(S1A)=Sof(C7A)=Sof(H7A)=Sof(C8A)=Sof(H8A)=Sof(C9A)=Sof(H9A)=FVAR(1)
 Fixed Sof: S1Z(0.25) S1B(0.75) C7Z(0.25) H7Z(0.25) C7B(0.75) H7B(0.75)
 C8B(0.75) H8B(0.75) C8Z(0.25) H8Z(0.25) C9Z(0.25) H9Z(0.25) C9B(0.75) H9B(0.75)
8.a Secondary CH2 refined with riding coordinates:
 C5B(H5BA,H5BB), C5A(H5AA,H5AB)
8.b Aromatic/amide H refined with riding coordinates:
 C7Z(H7Z), C7B(H7B), C8B(H8B), C8Z(H8Z), C9Z(H9Z), C9B(H9B), C7A(H7A),
 C7Y(H7Y), C8Y(H8Y), C8A(H8A), C9Y(H9Y), C9A(H9A)
8.c Idealised Me refined as rotating group:
 C3B(H3BA,H3BB,H3BC), C3A(H3AA,H3AB,H3AC)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
Br1B Br 0.75502(13) 0.09605(7) 0.40946(3) 0.0279(4) Uani 1 1 d . . . . .
S1Z S 0.7913(16) 0.1368(9) 0.7294(4) 0.0324(10) Uani 0.25 1 d D U P A 2
S1B S 0.5211(5) 0.1245(3) 0.63357(16) 0.0324(10) Uani 0.75 1 d . . P A 1
F1B F 0.8288(9) 0.4053(4) 0.5609(3) 0.062(2) Uani 1 1 d . . . . .
O1B O 0.9442(9) 0.2434(5) 0.5242(3) 0.040(2) Uani 1 1 d . . . . .
N1B N 0.9357(13) 0.2049(6) 0.5930(3) 0.035(3) Uani 1 1 d . . . . .
C1B C 0.7736(15) 0.1961(8) 0.5878(4) 0.032(3) Uani 1 1 d . . . . .
F2B F 0.8724(10) 0.4154(4) 0.4554(3) 0.069(2) Uani 1 1 d . . . . .
N2B N 0.6856(11) 0.2320(6) 0.5326(3) 0.035(3) Uani 1 1 d . . . . .
C2B C 0.7839(15) 0.2676(8) 0.4907(4) 0.035(3) Uani 1 1 d . . . . .
F3B F 0.6358(10) 0.4058(5) 0.4714(3) 0.066(2) Uani 1 1 d . . . . .
C3B C 1.0286(16) 0.1285(9) 0.6029(4) 0.052(4) Uani 1 1 d . . . . .
H3BA H 0.992341 0.084165 0.564439 0.079 Uiso 1 1 calc R U . . .
H3BB H 1.023626 0.099694 0.648391 0.079 Uiso 1 1 calc R U . . .
H3BC H 1.136812 0.146596 0.603031 0.079 Uiso 1 1 calc R U . . .
C4B C 0.7852(16) 0.3727(9) 0.4956(5) 0.047(4) Uani 1 1 d . . . . .
C5B C 0.7500(13) 0.2372(7) 0.4139(4) 0.039(3) Uani 1 1 d . . . . .
H5BA H 0.829437 0.263493 0.389598 0.047 Uiso 1 1 calc R U . . .
H5BB H 0.645776 0.260133 0.389549 0.047 Uiso 1 1 calc R U . . .
C6B C 0.7112(14) 0.1547(7) 0.6448(4) 0.036(3) Uani 1 1 d D U . . .
C7Z C 0.632(3) 0.103(3) 0.7579(14) 0.049(3) Uani 0.25 1 d D U P A 2
H7Z H 0.626300 0.086554 0.805063 0.059 Uiso 0.25 1 calc R U P A 2
C7B C 0.5421(18) 0.0873(12) 0.7212(6) 0.049(3) Uani 0.75 1 d D . P A 1
H7B H 0.460449 0.062312 0.741270 0.059 Uiso 0.75 1 calc R U P A 1
C8B C 0.6965(18) 0.0998(13) 0.7574(6) 0.049(3) Uani 0.75 1 d D . P A 1
H8B H 0.732314 0.085083 0.806146 0.059 Uiso 0.75 1 calc R U P A 1
C8Z C 0.509(3) 0.104(3) 0.6992(14) 0.049(3) Uani 0.25 1 d D U P A 2
H8Z H 0.406014 0.084862 0.701159 0.059 Uiso 0.25 1 calc R U P A 2
C9Z C 0.551(2) 0.135(3) 0.6359(13) 0.049(3) Uani 0.25 1 d D U P A 2
H9Z H 0.478536 0.142006 0.592138 0.059 Uiso 0.25 1 calc R U P A 2
C9B C 0.810(2) 0.1423(11) 0.7077(6) 0.049(3) Uani 0.75 1 d . . P A 1
H9B H 0.918686 0.155216 0.720197 0.059 Uiso 0.75 1 calc R U P A 1
Br1A Br 0.28846(12) 0.41254(6) 0.94014(3) 0.0211(3) Uani 1 1 d . U . . .
S1A S 0.5212(5) 0.3503(3) 0.71921(15) 0.0399(13) Uani 0.818(7) 1 d D . P B 1
S1Y S 0.232(3) 0.3562(16) 0.6223(6) 0.0399(13) Uani 0.182(7) 1 d D U P B 2
F1A F 0.1869(8) 0.0925(4) 0.7971(3) 0.061(2) Uani 1 1 d . . . . .
O1A O 0.0776(9) 0.2639(5) 0.8273(3) 0.040(2) Uani 1 1 d . . . . .
N1A N 0.0899(13) 0.3011(7) 0.7584(3) 0.044(3) Uani 1 1 d . . . . .
C1A C 0.2558(16) 0.2988(8) 0.7637(4) 0.039(4) Uani 1 1 d . . . . .
F2A F 0.3533(9) 0.0881(5) 0.8980(3) 0.062(2) Uani 1 1 d . . . . .
N2A N 0.3434(12) 0.2581(6) 0.8205(3) 0.043(3) Uani 1 1 d . . . . .
C2A C 0.2301(14) 0.2316(7) 0.8642(4) 0.032(3) Uani 1 1 d . U . . .
F3A F 0.1066(10) 0.0979(5) 0.8961(3) 0.071(3) Uani 1 1 d . . . . .
C3A C 0.0043(17) 0.3875(7) 0.7465(5) 0.056(4) Uani 1 1 d . . . . .
H3AA H 0.049107 0.432057 0.783576 0.085 Uiso 1 1 calc R U . . .
H3AB H -0.105850 0.376377 0.747703 0.085 Uiso 1 1 calc R U . . .
H3AC H 0.011429 0.412595 0.700032 0.085 Uiso 1 1 calc R U . . .
C4A C 0.2212(16) 0.1272(8) 0.8637(5) 0.044(4) Uani 1 1 d . . . . .
C5A C 0.2711(13) 0.2708(7) 0.9385(4) 0.041(3) Uani 1 1 d . U . . .
H5AA H 0.372039 0.244052 0.963528 0.049 Uiso 1 1 calc R U . . .
H5AB H 0.189848 0.251912 0.964610 0.049 Uiso 1 1 calc R U . . .
C6A C 0.3244(12) 0.3335(7) 0.7054(4) 0.044(3) Uani 1 1 d D U . . .
C7A C 0.5065(17) 0.3857(10) 0.6342(5) 0.049(3) Uani 0.818(7) 1 d D . P B 1
H7A H 0.593012 0.404960 0.615020 0.059 Uiso 0.818(7) 1 calc R U P B 1
C7Y C 0.407(4) 0.390(4) 0.606(2) 0.049(3) Uani 0.182(7) 1 d D U P B 2
H7Y H 0.417658 0.411821 0.560634 0.059 Uiso 0.182(7) 1 calc R U P B 2
C8Y C 0.532(3) 0.385(4) 0.662(2) 0.049(3) Uani 0.182(7) 1 d D U P B 2
H8Y H 0.636106 0.401287 0.661093 0.059 Uiso 0.182(7) 1 calc R U P B 2
C8A C 0.3526(18) 0.3831(12) 0.5959(6) 0.049(3) Uani 0.818(7) 1 d D . P B 1
H8A H 0.318835 0.399368 0.547406 0.059 Uiso 0.818(7) 1 calc R U P B 1
C9Y C 0.482(2) 0.350(4) 0.7224(18) 0.044(3) Uani 0.182(7) 1 d D U P B 2
H9Y H 0.548083 0.340408 0.767610 0.053 Uiso 0.182(7) 1 calc R U P B 2
C9A C 0.256(2) 0.3526(12) 0.6407(7) 0.044(3) Uani 0.818(7) 1 d . . P B 1
H9A H 0.145662 0.346177 0.624594 0.053 Uiso 0.818(7) 1 calc R U P B 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_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1B C5B 2.035(10) . ?
S1Z C6B 1.655(9) . ?
S1Z C7Z 1.674(15) . ?
S1B C6B 1.686(12) . ?
S1B C7B 1.746(11) . ?
F1B C4B 1.323(11) . ?
O1B N1B 1.454(9) . ?
O1B C2B 1.456(13) . ?
N1B C1B 1.404(12) . ?
N1B C3B 1.356(13) . ?
C1B N2B 1.284(11) . ?
C1B C6B 1.454(13) . ?
F2B C4B 1.344(13) . ?
N2B C2B 1.395(13) . ?
C2B C4B 1.517(16) . ?
C2B C5B 1.513(10) . ?
F3B C4B 1.375(14) . ?
C3B H3BA 0.9800 . ?
C3B H3BB 0.9800 . ?
C3B H3BC 0.9800 . ?
C5B H5BA 0.9900 . ?
C5B H5BB 0.9900 . ?
C6B C9Z 1.399(15) . ?
C6B C9B 1.344(17) . ?
C7Z H7Z 0.9500 . ?
C7Z C8Z 1.385(15) . ?
C7B H7B 0.9500 . ?
C7B C8B 1.395(15) . ?
C8B H8B 0.9500 . ?
C8B C9B 1.634(18) . ?
C8Z H8Z 0.9500 . ?
C8Z C9Z 1.420(15) . ?
C9Z H9Z 0.9500 . ?
C9B H9B 0.9500 . ?
Br1A C5A 2.046(10) . ?
S1A C6A 1.700(10) . ?
S1A C7A 1.696(10) . ?
S1Y C6A 1.669(10) . ?
S1Y C7Y 1.698(13) . ?
F1A C4A 1.353(10) . ?
O1A N1A 1.458(8) . ?
O1A C2A 1.449(12) . ?
N1A C1A 1.432(13) . ?
N1A C3A 1.445(13) . ?
C1A N2A 1.334(12) . ?
C1A C6A 1.469(13) . ?
F2A C4A 1.328(13) . ?
N2A C2A 1.477(13) . ?
C2A C4A 1.506(15) . ?
C2A C5A 1.513(10) . ?
F3A C4A 1.354(14) . ?
C3A H3AA 0.9800 . ?
C3A H3AB 0.9800 . ?
C3A H3AC 0.9800 . ?
C5A H5AA 0.9900 . ?
C5A H5AB 0.9900 . ?
C6A C9Y 1.370(16) . ?
C6A C9A 1.295(14) . ?
C7A H7A 0.9500 . ?
C7A C8A 1.392(13) . ?
C7Y H7Y 0.9500 . ?
C7Y C8Y 1.372(15) . ?
C8Y H8Y 0.9500 . ?
C8Y C9Y 1.406(16) . ?
C8A H8A 0.9500 . ?
C8A C9A 1.40(2) . ?
C9Y H9Y 0.9500 . ?
C9A H9A 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
C6B S1Z C7Z 99.2(12) . . ?
C6B S1B C7B 93.1(6) . . ?
N1B O1B C2B 105.5(8) . . ?
C1B N1B O1B 102.4(7) . . ?
C3B N1B O1B 107.1(8) . . ?
C3B N1B C1B 120.1(10) . . ?
N1B C1B C6B 121.1(9) . . ?
N2B C1B N1B 116.2(9) . . ?
N2B C1B C6B 122.6(12) . . ?
C1B N2B C2B 107.2(10) . . ?
O1B C2B C4B 102.6(10) . . ?
O1B C2B C5B 109.7(9) . . ?
N2B C2B O1B 107.8(7) . . ?
N2B C2B C4B 109.1(9) . . ?
N2B C2B C5B 116.3(9) . . ?
C5B C2B C4B 110.4(8) . . ?
N1B C3B H3BA 109.5 . . ?
N1B C3B H3BB 109.5 . . ?
N1B C3B H3BC 109.5 . . ?
H3BA C3B H3BB 109.5 . . ?
H3BA C3B H3BC 109.5 . . ?
H3BB C3B H3BC 109.5 . . ?
F1B C4B F2B 107.6(10) . . ?
F1B C4B C2B 114.2(8) . . ?
F1B C4B F3B 105.3(10) . . ?
F2B C4B C2B 114.7(10) . . ?
F2B C4B F3B 104.9(9) . . ?
F3B C4B C2B 109.3(11) . . ?
Br1B C5B H5BA 109.8 . . ?
Br1B C5B H5BB 109.8 . . ?
C2B C5B Br1B 109.2(6) . . ?
C2B C5B H5BA 109.8 . . ?
C2B C5B H5BB 109.8 . . ?
H5BA C5B H5BB 108.3 . . ?
C1B C6B S1Z 131.4(10) . . ?
C1B C6B S1B 121.6(7) . . ?
C9Z C6B S1Z 107.1(11) . . ?
C9Z C6B C1B 120.8(13) . . ?
C9B C6B S1B 120.6(9) . . ?
C9B C6B C1B 117.8(12) . . ?
S1Z C7Z H7Z 126.8 . . ?
C8Z C7Z S1Z 106.4(14) . . ?
C8Z C7Z H7Z 126.8 . . ?
S1B C7B H7B 125.1 . . ?
C8B C7B S1B 109.9(10) . . ?
C8B C7B H7B 125.1 . . ?
C7B C8B H8B 123.4 . . ?
C7B C8B C9B 113.3(11) . . ?
C9B C8B H8B 123.4 . . ?
C7Z C8Z H8Z 122.9 . . ?
C7Z C8Z C9Z 114.2(14) . . ?
C9Z C8Z H8Z 122.9 . . ?
C6B C9Z C8Z 112.9(12) . . ?
C6B C9Z H9Z 123.5 . . ?
C8Z C9Z H9Z 123.5 . . ?
C6B C9B C8B 103.1(13) . . ?
C6B C9B H9B 128.4 . . ?
C8B C9B H9B 128.4 . . ?
C7A S1A C6A 91.3(6) . . ?
C6A S1Y C7Y 87.8(14) . . ?
C2A O1A N1A 109.2(8) . . ?
C1A N1A O1A 101.1(7) . . ?
C1A N1A C3A 120.9(10) . . ?
C3A N1A O1A 109.1(8) . . ?
N1A C1A C6A 120.4(8) . . ?
N2A C1A N1A 117.8(9) . . ?
N2A C1A C6A 121.5(12) . . ?
C1A N2A C2A 104.1(10) . . ?
O1A C2A N2A 107.1(7) . . ?
O1A C2A C4A 106.1(9) . . ?
O1A C2A C5A 110.8(9) . . ?
N2A C2A C4A 107.1(9) . . ?
N2A C2A C5A 112.9(9) . . ?
C4A C2A C5A 112.3(8) . . ?
N1A C3A H3AA 109.5 . . ?
N1A C3A H3AB 109.5 . . ?
N1A C3A H3AC 109.5 . . ?
H3AA C3A H3AB 109.5 . . ?
H3AA C3A H3AC 109.5 . . ?
H3AB C3A H3AC 109.5 . . ?
F1A C4A C2A 112.0(8) . . ?
F1A C4A F3A 106.6(10) . . ?
F2A C4A F1A 108.2(10) . . ?
F2A C4A C2A 112.4(11) . . ?
F2A C4A F3A 106.8(9) . . ?
F3A C4A C2A 110.5(10) . . ?
Br1A C5A H5AA 109.0 . . ?
Br1A C5A H5AB 109.0 . . ?
C2A C5A Br1A 112.9(6) . . ?
C2A C5A H5AA 109.0 . . ?
C2A C5A H5AB 109.0 . . ?
H5AA C5A H5AB 107.8 . . ?
C1A C6A S1A 119.3(7) . . ?
C1A C6A S1Y 127.4(11) . . ?
C9Y C6A S1Y 117.2(15) . . ?
C9Y C6A C1A 115.4(16) . . ?
C9A C6A S1A 111.8(10) . . ?
C9A C6A C1A 128.9(13) . . ?
S1A C7A H7A 124.0 . . ?
C8A C7A S1A 111.9(10) . . ?
C8A C7A H7A 124.0 . . ?
S1Y C7Y H7Y 122.2 . . ?
C8Y C7Y S1Y 115.5(17) . . ?
C8Y C7Y H7Y 122.2 . . ?
C7Y C8Y H8Y 124.9 . . ?
C7Y C8Y C9Y 110.2(14) . . ?
C9Y C8Y H8Y 124.9 . . ?
C7A C8A H8A 125.6 . . ?
C7A C8A C9A 108.8(11) . . ?
C9A C8A H8A 125.6 . . ?
C6A C9Y C8Y 109.4(13) . . ?
C6A C9Y H9Y 125.3 . . ?
C8Y C9Y H9Y 125.3 . . ?
C6A C9A C8A 116.2(15) . . ?
C6A C9A H9A 121.9 . . ?
C8A C9A H9A 121.9 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
S1Z C6B C9Z C8Z -2(3) . . . . ?
S1Z C7Z C8Z C9Z -2(3) . . . . ?
S1B C6B C9B C8B -1.5(16) . . . . ?
S1B C7B C8B C9B -1.2(18) . . . . ?
O1B N1B C1B N2B -7.9(12) . . . . ?
O1B N1B C1B C6B 176.6(8) . . . . ?
O1B C2B C4B F1B -57.0(12) . . . . ?
O1B C2B C4B F2B 67.9(10) . . . . ?
O1B C2B C4B F3B -174.6(7) . . . . ?
O1B C2B C5B Br1B 66.2(9) . . . . ?
N1B O1B C2B N2B -8.7(10) . . . . ?
N1B O1B C2B C4B 106.4(8) . . . . ?
N1B O1B C2B C5B -136.3(8) . . . . ?
N1B C1B N2B C2B 2.5(12) . . . . ?
N1B C1B C6B S1Z 18.7(17) . . . . ?
N1B C1B C6B S1B -167.9(8) . . . . ?
N1B C1B C6B C9Z -172(2) . . . . ?
N1B C1B C6B C9B 13.2(16) . . . . ?
C1B N2B C2B O1B 4.1(11) . . . . ?
C1B N2B C2B C4B -106.6(10) . . . . ?
C1B N2B C2B C5B 127.8(10) . . . . ?
C1B C6B C9Z C8Z -174(2) . . . . ?
C1B C6B C9B C8B 177.5(10) . . . . ?
N2B C1B C6B S1Z -156.6(10) . . . . ?
N2B C1B C6B S1B 16.8(14) . . . . ?
N2B C1B C6B C9Z 13(3) . . . . ?
N2B C1B C6B C9B -162.1(12) . . . . ?
N2B C2B C4B F1B 57.2(14) . . . . ?
N2B C2B C4B F2B -178.0(9) . . . . ?
N2B C2B C4B F3B -60.5(10) . . . . ?
N2B C2B C5B Br1B -56.5(12) . . . . ?
C2B O1B N1B C1B 9.4(10) . . . . ?
C2B O1B N1B C3B 136.6(10) . . . . ?
C3B N1B C1B N2B -126.2(9) . . . . ?
C3B N1B C1B C6B 58.2(12) . . . . ?
C4B C2B C5B Br1B 178.5(9) . . . . ?
C5B C2B C4B F1B -173.8(10) . . . . ?
C5B C2B C4B F2B -49.0(15) . . . . ?
C5B C2B C4B F3B 68.5(12) . . . . ?
C6B S1Z C7Z C8Z 1.0(15) . . . . ?
C6B S1B C7B C8B 0.4(13) . . . . ?
C6B C1B N2B C2B 178.0(9) . . . . ?
C7Z S1Z C6B C1B 171.3(18) . . . . ?
C7Z S1Z C6B C9Z 0.6(16) . . . . ?
C7Z C8Z C9Z C6B 3(4) . . . . ?
C7B S1B C6B C1B -178.1(10) . . . . ?
C7B S1B C6B C9B 0.8(13) . . . . ?
C7B C8B C9B C6B 1.7(18) . . . . ?
S1A C6A C9A C8A -0.5(19) . . . . ?
S1A C7A C8A C9A 0.8(16) . . . . ?
S1Y C6A C9Y C8Y 0(3) . . . . ?
S1Y C7Y C8Y C9Y 0(3) . . . . ?
O1A N1A C1A N2A 6.8(12) . . . . ?
O1A N1A C1A C6A -178.1(9) . . . . ?
O1A C2A C4A F1A 59.7(13) . . . . ?
O1A C2A C4A F2A -178.1(8) . . . . ?
O1A C2A C4A F3A -59.0(9) . . . . ?
O1A C2A C5A Br1A -62.8(10) . . . . ?
N1A O1A C2A N2A 6.0(10) . . . . ?
N1A O1A C2A C4A -108.2(9) . . . . ?
N1A O1A C2A C5A 129.6(8) . . . . ?
N1A C1A N2A C2A -3.3(12) . . . . ?
N1A C1A C6A S1A 167.8(8) . . . . ?
N1A C1A C6A S1Y -14.8(18) . . . . ?
N1A C1A C6A C9Y 164(3) . . . . ?
N1A C1A C6A C9A -14(2) . . . . ?
C1A N2A C2A O1A -1.8(10) . . . . ?
C1A N2A C2A C4A 111.7(9) . . . . ?
C1A N2A C2A C5A -124.1(9) . . . . ?
C1A C6A C9Y C8Y -179(2) . . . . ?
C1A C6A C9A C8A -178.7(12) . . . . ?
N2A C1A C6A S1A -17.3(15) . . . . ?
N2A C1A C6A S1Y 160.1(13) . . . . ?
N2A C1A C6A C9Y -21(3) . . . . ?
N2A C1A C6A C9A 160.8(14) . . . . ?
N2A C2A C4A F1A -54.5(13) . . . . ?
N2A C2A C4A F2A 67.7(10) . . . . ?
N2A C2A C4A F3A -173.1(8) . . . . ?
N2A C2A C5A Br1A 57.4(11) . . . . ?
C2A O1A N1A C1A -7.3(10) . . . . ?
C2A O1A N1A C3A -135.7(9) . . . . ?
C3A N1A C1A N2A 127.2(10) . . . . ?
C3A N1A C1A C6A -57.8(12) . . . . ?
C4A C2A C5A Br1A 178.7(9) . . . . ?
C5A C2A C4A F1A -179.0(9) . . . . ?
C5A C2A C4A F2A -56.9(14) . . . . ?
C5A C2A C4A F3A 62.3(13) . . . . ?
C6A S1A C7A C8A -0.9(11) . . . . ?
C6A S1Y C7Y C8Y -0.2(16) . . . . ?
C6A C1A N2A C2A -178.3(9) . . . . ?
C7A S1A C6A C1A 179.2(10) . . . . ?
C7A S1A C6A C9A 0.8(12) . . . . ?
C7A C8A C9A C6A 0(2) . . . . ?
C7Y S1Y C6A C1A 179(2) . . . . ?
C7Y S1Y C6A C9Y 0.1(17) . . . . ?
C7Y C8Y C9Y C6A 0(4) . . . . ?

####################################################################### 
# 
# 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_dc721
_database_code_depnum_ccdc_archive 'CCDC 2493078'
loop_
_audit_author_name
_audit_author_address
'Alexander Prado-Roler'
;University of Vienna
Austria
;
_audit_update_record             
;
2025-10-03 deposited with the CCDC.	2026-01-08 downloaded from the CCDC.
;
_audit_creation_date             2025-07-10
_audit_creation_method           
;
Olex2 1.5-alpha
(compiled 2025.07.01 svn.ra095ee60 for OlexSys, GUI svn.r7302)
;
# start Validation Reply Form
_vrf_PLAT029_dc721               
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.954 Why?
RESPONSE: Our detector ('EIGER2 500K') somtimes can not reach all reflection 
with the software calculating the runlist. 95.4% is fine because the
quality of the measurement is good. We decided not to measure another 
orientation of the crystal.
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H13 Cl2 F3 N2 O'
_chemical_formula_sum            'C17 H13 Cl2 F3 N2 O'
_chemical_formula_weight         389.19
_chemical_melting_point          ?
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'
Cl Cl 0.3639 0.7018 '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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   10.8042(4)
_cell_length_b                   13.9249(4)
_cell_length_c                   11.1764(4)
_cell_angle_alpha                90
_cell_angle_beta                 99.627(3)
_cell_angle_gamma                90
_cell_volume                     1657.78(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    80555
_cell_measurement_temperature    100
_cell_measurement_theta_max      72.26
_cell_measurement_theta_min      4.01
_shelx_estimated_absorpt_T_max   0.800
_shelx_estimated_absorpt_T_min   0.351
_exptl_absorpt_coefficient_mu    3.899
_exptl_absorpt_correction_T_max  0.8864
_exptl_absorpt_correction_T_min  0.6382
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
STOE LANA, absorption correction by scaling of reflection intensities.
J. Koziskova, F. Hahn, J. Richter, J. Kozisek, "Comparison of different
absorption corrections on the model structure of tetrakis(μ₂-acetato)-
diaqua-di-copper(II)", Acta Chimica Slovaca, vol. 9, no. 2, 2016, pp. 136 - 140.
Afterwards a spherical absorption correction was performed within STOE LANA.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_density_diffrn    1.559
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             792
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.06
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0218
_diffrn_reflns_av_unetI/netI     0.0116
_diffrn_reflns_Laue_measured_fraction_full 0.954
_diffrn_reflns_Laue_measured_fraction_max 0.913
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            23115
_diffrn_reflns_point_group_measured_fraction_full 0.954
_diffrn_reflns_point_group_measured_fraction_max 0.913
_diffrn_reflns_theta_full        67.686
_diffrn_reflns_theta_max         70.635
_diffrn_reflns_theta_min         5.119
_diffrn_ambient_temperature      100
_diffrn_detector                 'EIGER2 500K'
_diffrn_detector_area_resol_mean 13.33
_diffrn_measured_fraction_theta_full 0.954
_diffrn_measured_fraction_theta_max 0.913
_diffrn_measurement_details      
;
 11276 frames, detector distance = 40 mm
;
_diffrn_measurement_device       'Eulerian 4-circle diffractometer'
_diffrn_measurement_device_type  'STOE STADIVARI'
_diffrn_measurement_method       'rotation method, ω scans'
_diffrn_radiation_collimation    '1.2 mm, 0.6 diameter'
_diffrn_radiation_monochromator  'Graded multilayer mirror'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54186
_diffrn_source                   'Primux 100 micro'
_diffrn_source_current           1.00
_diffrn_source_power             0.050
_diffrn_source_voltage           50
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2738
_reflns_number_total             2913
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
X-Area Recipe 2.0.2 (STOE, 2024)
;
_computing_data_collection       
;
X-Area Pilatus3_SV 1.31.194.0 (STOE, 2023)
;
_computing_data_reduction        
;
X-Area Integrate 2.5.18.0 (STOE, 2024)
X-Area LANA 2.8.4 (STOE, 2024)
;
_computing_molecular_graphics    'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.939
_refine_diff_density_min         -0.632
_refine_diff_density_rms         0.088
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         2913
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0589
_refine_ls_R_factor_gt           0.0566
_refine_ls_restrained_S_all      1.072
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0921P)²+3.2552P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1573
_refine_ls_wR_factor_ref         0.1593
_refine_special_details          
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C5(H5A,H5B)
2.b Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C10(H10), C11(H11), C13(H13), C14(H14), C15(H15), C16(H16),
 C17(H17)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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 0.73156(8) 0.35129(6) 0.10185(8) 0.0356(3) Uani 1 1 d . . . . .
F1 F 0.5997(2) 0.66271(13) 0.27947(18) 0.0346(5) Uani 1 1 d . . . . .
O1 O 0.54351(19) 0.47383(15) 0.21376(18) 0.0215(5) Uani 1 1 d . . . . .
N1 N 0.5638(2) 0.43668(18) 0.3380(2) 0.0176(5) Uani 1 1 d . . . . .
C1 C 0.6922(3) 0.4536(2) 0.3794(3) 0.0195(6) Uani 1 1 d . . . . .
Cl2 Cl 0.95130(7) 0.40868(5) 0.88995(7) 0.0263(2) Uani 1 1 d . . . . .
F2 F 0.7369(2) 0.67221(14) 0.1614(2) 0.0378(5) Uani 1 1 d . . . . .
N2 N 0.7499(2) 0.5006(2) 0.3054(2) 0.0233(6) Uani 1 1 d . . . . .
C2 C 0.6607(3) 0.5164(2) 0.1966(3) 0.0232(7) Uani 1 1 d . . . . .
F3 F 0.54329(19) 0.64323(15) 0.08689(18) 0.0356(5) Uani 1 1 d . . . . .
C3 C 0.5182(3) 0.3363(2) 0.3342(3) 0.0201(6) Uani 1 1 d . . . . .
H3A H 0.544982 0.305731 0.414303 0.024 Uiso 1 1 calc R U . . .
H3B H 0.555419 0.299691 0.273106 0.024 Uiso 1 1 calc R U . . .
C4 C 0.6371(3) 0.6268(3) 0.1827(3) 0.0281(7) Uani 1 1 d . . . . .
C5 C 0.7021(3) 0.4769(2) 0.0828(3) 0.0291(7) Uani 1 1 d . . . . .
H5A H 0.779201 0.510134 0.068352 0.035 Uiso 1 1 calc R U . . .
H5B H 0.635604 0.487930 0.011647 0.035 Uiso 1 1 calc R U . . .
C6 C 0.7511(3) 0.4285(2) 0.5034(3) 0.0184(6) Uani 1 1 d . . . . .
C7 C 0.8813(3) 0.4183(2) 0.5283(3) 0.0218(6) Uani 1 1 d . . . . .
H7 H 0.927972 0.417408 0.463410 0.026 Uiso 1 1 calc R U . . .
C8 C 0.9433(3) 0.4096(2) 0.6466(3) 0.0218(6) Uani 1 1 d . . . . .
H8 H 1.031942 0.402522 0.663557 0.026 Uiso 1 1 calc R U . . .
C9 C 0.8731(3) 0.4112(2) 0.7400(3) 0.0199(6) Uani 1 1 d . . . . .
C10 C 0.7433(3) 0.4176(2) 0.7173(3) 0.0200(6) Uani 1 1 d . . . . .
H10 H 0.696880 0.415941 0.782295 0.024 Uiso 1 1 calc R U . . .
C11 C 0.6824(3) 0.4264(2) 0.5992(3) 0.0183(6) Uani 1 1 d . . . . .
H11 H 0.593493 0.431019 0.582714 0.022 Uiso 1 1 calc R U . . .
C12 C 0.3764(3) 0.33367(19) 0.3020(3) 0.0187(6) Uani 1 1 d . . . . .
C13 C 0.3186(3) 0.3323(2) 0.1808(3) 0.0261(7) Uani 1 1 d . . . . .
H13 H 0.368507 0.330639 0.118489 0.031 Uiso 1 1 calc R U . . .
C14 C 0.1890(4) 0.3335(2) 0.1506(4) 0.0386(9) Uani 1 1 d . . . . .
H14 H 0.150141 0.333156 0.067769 0.046 Uiso 1 1 calc R U . . .
C15 C 0.1163(3) 0.3350(2) 0.2415(5) 0.0450(11) Uani 1 1 d . . . . .
H15 H 0.027391 0.336732 0.221126 0.054 Uiso 1 1 calc R U . . .
C16 C 0.1729(3) 0.3342(2) 0.3612(4) 0.0383(9) Uani 1 1 d . . . . .
H16 H 0.122623 0.333853 0.423328 0.046 Uiso 1 1 calc R U . . .
C17 C 0.3027(3) 0.3338(2) 0.3920(3) 0.0256(7) Uani 1 1 d . . . . .
H17 H 0.341050 0.333591 0.474949 0.031 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C5 1.784(4) . ?
F1 C4 1.314(4) . ?
O1 N1 1.464(3) . ?
O1 C2 1.439(4) . ?
N1 C1 1.407(4) . ?
N1 C3 1.480(4) . ?
C1 N2 1.294(4) . ?
C1 C6 1.468(4) . ?
Cl2 C9 1.746(3) . ?
F2 C4 1.305(4) . ?
N2 C2 1.437(4) . ?
C2 C4 1.562(5) . ?
C2 C5 1.521(4) . ?
F3 C4 1.365(4) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C12 1.515(4) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C7 1.395(4) . ?
C6 C11 1.401(4) . ?
C7 H7 0.9500 . ?
C7 C8 1.383(5) . ?
C8 H8 0.9500 . ?
C8 C9 1.389(4) . ?
C9 C10 1.386(4) . ?
C10 H10 0.9500 . ?
C10 C11 1.378(4) . ?
C11 H11 0.9500 . ?
C12 C13 1.394(5) . ?
C12 C17 1.383(4) . ?
C13 H13 0.9500 . ?
C13 C14 1.384(5) . ?
C14 H14 0.9500 . ?
C14 C15 1.384(6) . ?
C15 H15 0.9500 . ?
C15 C16 1.375(6) . ?
C16 H16 0.9500 . ?
C16 C17 1.388(5) . ?
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
C2 O1 N1 106.0(2) . . ?
O1 N1 C3 108.1(2) . . ?
C1 N1 O1 103.6(2) . . ?
C1 N1 C3 118.2(2) . . ?
N1 C1 C6 121.2(2) . . ?
N2 C1 N1 115.4(3) . . ?
N2 C1 C6 123.0(3) . . ?
C1 N2 C2 106.9(2) . . ?
O1 C2 C4 106.7(3) . . ?
O1 C2 C5 110.5(3) . . ?
N2 C2 O1 107.8(2) . . ?
N2 C2 C4 108.1(3) . . ?
N2 C2 C5 113.7(3) . . ?
C5 C2 C4 109.8(3) . . ?
N1 C3 H3A 109.6 . . ?
N1 C3 H3B 109.6 . . ?
N1 C3 C12 110.4(2) . . ?
H3A C3 H3B 108.1 . . ?
C12 C3 H3A 109.6 . . ?
C12 C3 H3B 109.6 . . ?
F1 C4 C2 111.1(2) . . ?
F1 C4 F3 107.0(3) . . ?
F2 C4 F1 110.1(3) . . ?
F2 C4 C2 111.7(3) . . ?
F2 C4 F3 107.6(2) . . ?
F3 C4 C2 109.3(3) . . ?
Cl1 C5 H5A 109.9 . . ?
Cl1 C5 H5B 109.9 . . ?
C2 C5 Cl1 109.1(2) . . ?
C2 C5 H5A 109.9 . . ?
C2 C5 H5B 109.9 . . ?
H5A C5 H5B 108.3 . . ?
C7 C6 C1 118.4(3) . . ?
C7 C6 C11 119.4(3) . . ?
C11 C6 C1 121.7(3) . . ?
C6 C7 H7 119.7 . . ?
C8 C7 C6 120.7(3) . . ?
C8 C7 H7 119.7 . . ?
C7 C8 H8 120.7 . . ?
C7 C8 C9 118.6(3) . . ?
C9 C8 H8 120.7 . . ?
C8 C9 Cl2 118.9(2) . . ?
C10 C9 Cl2 119.3(2) . . ?
C10 C9 C8 121.7(3) . . ?
C9 C10 H10 120.4 . . ?
C11 C10 C9 119.2(3) . . ?
C11 C10 H10 120.4 . . ?
C6 C11 H11 119.8 . . ?
C10 C11 C6 120.3(3) . . ?
C10 C11 H11 119.8 . . ?
C13 C12 C3 120.1(3) . . ?
C17 C12 C3 120.7(3) . . ?
C17 C12 C13 119.2(3) . . ?
C12 C13 H13 119.7 . . ?
C14 C13 C12 120.5(3) . . ?
C14 C13 H13 119.7 . . ?
C13 C14 H14 120.2 . . ?
C15 C14 C13 119.7(4) . . ?
C15 C14 H14 120.2 . . ?
C14 C15 H15 120.0 . . ?
C16 C15 C14 120.0(3) . . ?
C16 C15 H15 120.0 . . ?
C15 C16 H16 119.8 . . ?
C15 C16 C17 120.5(4) . . ?
C17 C16 H16 119.8 . . ?
C12 C17 C16 120.1(3) . . ?
C12 C17 H17 120.0 . . ?
C16 C17 H17 120.0 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 N1 C1 N2 5.0(3) . . . . ?
O1 N1 C1 C6 178.5(2) . . . . ?
O1 N1 C3 C12 -69.7(3) . . . . ?
O1 C2 C4 F1 59.5(3) . . . . ?
O1 C2 C4 F2 -177.3(2) . . . . ?
O1 C2 C4 F3 -58.3(3) . . . . ?
O1 C2 C5 Cl1 -63.8(3) . . . . ?
N1 O1 C2 N2 2.9(3) . . . . ?
N1 O1 C2 C4 -113.0(2) . . . . ?
N1 O1 C2 C5 127.7(3) . . . . ?
N1 C1 N2 C2 -3.2(4) . . . . ?
N1 C1 C6 C7 160.3(3) . . . . ?
N1 C1 C6 C11 -27.8(4) . . . . ?
N1 C3 C12 C13 87.1(3) . . . . ?
N1 C3 C12 C17 -92.1(3) . . . . ?
C1 N1 C3 C12 173.2(2) . . . . ?
C1 N2 C2 O1 0.0(3) . . . . ?
C1 N2 C2 C4 114.9(3) . . . . ?
C1 N2 C2 C5 -122.9(3) . . . . ?
C1 C6 C7 C8 169.9(3) . . . . ?
C1 C6 C11 C10 -169.7(3) . . . . ?
Cl2 C9 C10 C11 175.5(2) . . . . ?
N2 C1 C6 C7 -26.7(4) . . . . ?
N2 C1 C6 C11 145.2(3) . . . . ?
N2 C2 C4 F1 -56.2(3) . . . . ?
N2 C2 C4 F2 67.1(3) . . . . ?
N2 C2 C4 F3 -173.9(2) . . . . ?
N2 C2 C5 Cl1 57.6(3) . . . . ?
C2 O1 N1 C1 -4.5(3) . . . . ?
C2 O1 N1 C3 -130.7(2) . . . . ?
C3 N1 C1 N2 124.4(3) . . . . ?
C3 N1 C1 C6 -62.0(4) . . . . ?
C3 C12 C13 C14 -177.6(3) . . . . ?
C3 C12 C17 C16 178.1(3) . . . . ?
C4 C2 C5 Cl1 178.8(2) . . . . ?
C5 C2 C4 F1 179.3(3) . . . . ?
C5 C2 C4 F2 -57.5(4) . . . . ?
C5 C2 C4 F3 61.5(3) . . . . ?
C6 C1 N2 C2 -176.6(3) . . . . ?
C6 C7 C8 C9 -0.1(4) . . . . ?
C7 C6 C11 C10 2.2(4) . . . . ?
C7 C8 C9 Cl2 -175.6(2) . . . . ?
C7 C8 C9 C10 2.6(4) . . . . ?
C8 C9 C10 C11 -2.7(4) . . . . ?
C9 C10 C11 C6 0.2(4) . . . . ?
C11 C6 C7 C8 -2.2(4) . . . . ?
C12 C13 C14 C15 -0.6(5) . . . . ?
C13 C12 C17 C16 -1.1(4) . . . . ?
C13 C14 C15 C16 -0.9(5) . . . . ?
C14 C15 C16 C17 1.4(5) . . . . ?
C15 C16 C17 C12 -0.4(5) . . . . ?
C17 C12 C13 C14 1.6(4) . . . . ?

####################################################################### 
# 
# 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_dc723
_database_code_depnum_ccdc_archive 'CCDC 2493079'
loop_
_audit_author_name
_audit_author_address
'Alexander Prado-Roler'
;University of Vienna
Austria
;
_audit_update_record             
;
2025-10-03 deposited with the CCDC.	2026-01-08 downloaded from the CCDC.
;
_audit_creation_date             2025-07-07
_audit_creation_method           
;
Olex2 1.5-alpha
(compiled 2025.07.01 svn.ra095ee60 for OlexSys, GUI svn.r7302)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C9 H8 F4 N2 O S'
_chemical_formula_sum            'C9 H8 F4 N2 O S'
_chemical_formula_weight         268.23
_chemical_melting_point          ?
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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   7.6657(5)
_cell_length_b                   11.8373(8)
_cell_length_c                   24.323(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2207.1(3)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    20760
_cell_measurement_temperature    100
_cell_measurement_theta_max      29.78
_cell_measurement_theta_min      3.14
_shelx_estimated_absorpt_T_max   0.997
_shelx_estimated_absorpt_T_min   0.907
_exptl_absorpt_coefficient_mu    0.333
_exptl_absorpt_correction_T_max  0.9996
_exptl_absorpt_correction_T_min  0.9881
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
STOE LANA, absorption correction by scaling of reflection intensities.
J. Koziskova, F. Hahn, J. Richter, J. Kozisek, "Comparison of different
absorption corrections on the model structure of tetrakis(μ₂-acetato)-
diaqua-di-copper(II)", Acta Chimica Slovaca, vol. 9, no. 2, 2016, pp. 136 - 140.
Afterwards a spherical absorption correction was performed within STOE LANA.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_density_diffrn    1.614
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1088
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.187
_exptl_crystal_size_min          0.01
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1131
_diffrn_reflns_av_unetI/netI     0.0545
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            31974
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.347
_diffrn_reflns_theta_min         3.141
_diffrn_ambient_temperature      100
_diffrn_detector                 'EIGER2 500K'
_diffrn_detector_area_resol_mean 13.33
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
 4569 frames, detector distance = 50 mm
;
_diffrn_measurement_device       'Eulerian 4-circle diffractometer'
_diffrn_measurement_device_type  'STOE STADIVARI'
_diffrn_measurement_method       'rotation method, ω scans'
_diffrn_radiation_collimation    '1.2 0.6 mm diameter'
_diffrn_radiation_monochromator  'Graded multilayer mirror'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Axo Mo'
_diffrn_source_current           0.830
_diffrn_source_power             0.050
_diffrn_source_voltage           60
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1297
_reflns_number_total             2020
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
X-Area Recipe 2.0.1 (STOE, 2023)
;
_computing_data_collection       
;
X-Area Pilatus3_SV 1.31.192.0 (STOE, 2023)
;
_computing_data_reduction        
;
X-Area Integrate 2.5.15.0 (STOE, 2023)
X-Area LANA 2.7.12 (STOE, 2023)
;
_computing_molecular_graphics    'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.546
_refine_diff_density_min         -0.368
_refine_diff_density_rms         0.070
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.999
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         2020
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0728
_refine_ls_R_factor_gt           0.0421
_refine_ls_restrained_S_all      0.999
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0705P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1107
_refine_ls_wR_factor_ref         0.1207
_refine_special_details          
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B)
2.b Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C9(H9)
2.c Idealised Me refined as rotating group:
 C3(H3A,H3B,H3C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
S1 S 0.65486(10) 0.68753(6) 0.48056(3) 0.0233(2) Uani 1 1 d . . . . .
F1 F 0.0565(2) 0.57467(17) 0.37901(7) 0.0384(5) Uani 1 1 d . . . . .
O1 O 0.3383(2) 0.59332(18) 0.30997(8) 0.0236(5) Uani 1 1 d . . . . .
N1 N 0.4629(3) 0.5360(2) 0.34576(10) 0.0194(6) Uani 1 1 d . . . . .
C1 C 0.4761(4) 0.6087(3) 0.39103(12) 0.0177(7) Uani 1 1 d . . . . .
F2 F 0.0151(2) 0.75286(19) 0.38208(8) 0.0435(6) Uani 1 1 d . . . . .
N2 N 0.3725(3) 0.6934(2) 0.39161(10) 0.0204(6) Uani 1 1 d . . . . .
C2 C 0.2784(4) 0.6900(3) 0.34026(12) 0.0205(7) Uani 1 1 d . . . . .
F3 F -0.0081(2) 0.66377(19) 0.30521(7) 0.0403(6) Uani 1 1 d . . . . .
C3 C 0.6192(4) 0.5151(3) 0.31240(13) 0.0331(9) Uani 1 1 d . . . . .
H3A H 0.588479 0.467769 0.280801 0.050 Uiso 1 1 calc R U . . .
H3B H 0.707179 0.476401 0.334762 0.050 Uiso 1 1 calc R U . . .
H3C H 0.666403 0.587254 0.299360 0.050 Uiso 1 1 calc R U . . .
F4 F 0.4800(2) 0.81455(17) 0.29956(8) 0.0406(6) Uani 1 1 d . . . . .
C4 C 0.0835(4) 0.6699(3) 0.35195(13) 0.0275(8) Uani 1 1 d . . . . .
C5 C 0.3019(4) 0.7967(3) 0.30597(14) 0.0290(8) Uani 1 1 d . . . . .
H5A H 0.245636 0.787327 0.269619 0.035 Uiso 1 1 calc R U . . .
H5B H 0.247729 0.862006 0.324770 0.035 Uiso 1 1 calc R U . . .
C6 C 0.5983(3) 0.5823(2) 0.43544(11) 0.0168(7) Uani 1 1 d . . . . .
C7 C 0.7777(3) 0.5964(3) 0.51826(13) 0.0217(7) Uani 1 1 d . . . . .
H7 H 0.840532 0.617561 0.550309 0.026 Uiso 1 1 calc R U . . .
C8 C 0.7760(4) 0.4900(3) 0.49743(12) 0.0205(7) Uani 1 1 d . . . . .
H8 H 0.837592 0.428559 0.513417 0.025 Uiso 1 1 calc R U . . .
C9 C 0.6725(3) 0.4800(2) 0.44923(12) 0.0163(7) Uani 1 1 d . . . . .
H9 H 0.656446 0.411940 0.429171 0.020 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
S1 C6 1.716(3) . ?
S1 C7 1.700(3) . ?
F1 C4 1.322(4) . ?
O1 N1 1.460(3) . ?
O1 C2 1.436(3) . ?
N1 C1 1.401(4) . ?
N1 C3 1.468(3) . ?
C1 N2 1.279(4) . ?
C1 C6 1.464(4) . ?
F2 C4 1.332(4) . ?
N2 C2 1.443(4) . ?
C2 C4 1.539(4) . ?
C2 C5 1.524(4) . ?
F3 C4 1.338(3) . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
F4 C5 1.390(3) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C9 1.379(4) . ?
C7 H7 0.9500 . ?
C7 C8 1.358(4) . ?
C8 H8 0.9500 . ?
C8 C9 1.421(4) . ?
C9 H9 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7 S1 C6 91.38(15) . . ?
C2 O1 N1 105.89(19) . . ?
O1 N1 C3 106.4(2) . . ?
C1 N1 O1 103.3(2) . . ?
C1 N1 C3 118.6(2) . . ?
N1 C1 C6 119.6(3) . . ?
N2 C1 N1 116.5(3) . . ?
N2 C1 C6 123.9(3) . . ?
C1 N2 C2 106.2(2) . . ?
O1 C2 N2 107.8(2) . . ?
O1 C2 C4 106.4(2) . . ?
O1 C2 C5 110.0(2) . . ?
N2 C2 C4 109.2(2) . . ?
N2 C2 C5 113.1(2) . . ?
C5 C2 C4 110.1(2) . . ?
N1 C3 H3A 109.5 . . ?
N1 C3 H3B 109.5 . . ?
N1 C3 H3C 109.5 . . ?
H3A C3 H3B 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
F1 C4 F2 107.0(3) . . ?
F1 C4 C2 112.1(3) . . ?
F1 C4 F3 107.1(3) . . ?
F2 C4 C2 111.7(3) . . ?
F2 C4 F3 107.5(2) . . ?
F3 C4 C2 111.2(3) . . ?
C2 C5 H5A 110.2 . . ?
C2 C5 H5B 110.2 . . ?
F4 C5 C2 107.7(2) . . ?
F4 C5 H5A 110.2 . . ?
F4 C5 H5B 110.2 . . ?
H5A C5 H5B 108.5 . . ?
C1 C6 S1 118.6(2) . . ?
C9 C6 S1 112.2(2) . . ?
C9 C6 C1 129.2(3) . . ?
S1 C7 H7 123.8 . . ?
C8 C7 S1 112.5(2) . . ?
C8 C7 H7 123.8 . . ?
C7 C8 H8 123.5 . . ?
C7 C8 C9 113.0(3) . . ?
C9 C8 H8 123.5 . . ?
C6 C9 C8 111.0(3) . . ?
C6 C9 H9 124.5 . . ?
C8 C9 H9 124.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
S1 C6 C9 C8 0.1(3) . . . . ?
S1 C7 C8 C9 0.0(3) . . . . ?
O1 N1 C1 N2 5.9(3) . . . . ?
O1 N1 C1 C6 -176.9(2) . . . . ?
O1 C2 C4 F1 57.3(3) . . . . ?
O1 C2 C4 F2 177.4(2) . . . . ?
O1 C2 C4 F3 -62.5(3) . . . . ?
O1 C2 C5 F4 -66.7(3) . . . . ?
N1 O1 C2 N2 3.0(3) . . . . ?
N1 O1 C2 C4 -114.1(2) . . . . ?
N1 O1 C2 C5 126.7(2) . . . . ?
N1 C1 N2 C2 -4.1(3) . . . . ?
N1 C1 C6 S1 163.1(2) . . . . ?
N1 C1 C6 C9 -20.7(4) . . . . ?
C1 N2 C2 O1 0.4(3) . . . . ?
C1 N2 C2 C4 115.6(3) . . . . ?
C1 N2 C2 C5 -121.4(3) . . . . ?
C1 C6 C9 C8 -176.4(3) . . . . ?
N2 C1 C6 S1 -20.0(4) . . . . ?
N2 C1 C6 C9 156.3(3) . . . . ?
N2 C2 C4 F1 -58.8(3) . . . . ?
N2 C2 C4 F2 61.3(3) . . . . ?
N2 C2 C4 F3 -178.6(2) . . . . ?
N2 C2 C5 F4 53.8(3) . . . . ?
C2 O1 N1 C1 -5.0(3) . . . . ?
C2 O1 N1 C3 -130.6(2) . . . . ?
C3 N1 C1 N2 123.3(3) . . . . ?
C3 N1 C1 C6 -59.5(4) . . . . ?
C4 C2 C5 F4 176.4(3) . . . . ?
C5 C2 C4 F1 176.4(2) . . . . ?
C5 C2 C4 F2 -63.4(3) . . . . ?
C5 C2 C4 F3 56.6(3) . . . . ?
C6 S1 C7 C8 0.0(2) . . . . ?
C6 C1 N2 C2 178.9(3) . . . . ?
C7 S1 C6 C1 176.8(2) . . . . ?
C7 S1 C6 C9 0.0(2) . . . . ?
C7 C8 C9 C6 -0.1(3) . . . . ?

####################################################################### 
# 
# 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_dc747
_database_code_depnum_ccdc_archive 'CCDC 2493080'
loop_
_audit_author_name
_audit_author_address
'Alexander Prado-Roler'
;University of Vienna
Austria
;
_audit_update_record             
;
2025-10-03 deposited with the CCDC.	2026-01-08 downloaded from the CCDC.
;
_audit_creation_date             2025-07-07
_audit_creation_method           
;
Olex2 1.5-alpha
(compiled 2025.07.01 svn.ra095ee60 for OlexSys, GUI svn.r7302)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C11 H9 Br F3 I N2 O'
_chemical_formula_sum            'C11 H9 Br F3 I N2 O'
_chemical_formula_weight         449.01
_chemical_melting_point          ?
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'
I I -0.4742 1.8119 '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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   13.9854(13)
_cell_length_b                   12.3430(14)
_cell_length_c                   8.1470(7)
_cell_angle_alpha                90
_cell_angle_beta                 102.027(7)
_cell_angle_gamma                90
_cell_volume                     1375.5(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    31742
_cell_measurement_temperature    100
_cell_measurement_theta_max      29.85
_cell_measurement_theta_min      3.14
_shelx_estimated_absorpt_T_max   0.621
_shelx_estimated_absorpt_T_min   0.227
_exptl_absorpt_coefficient_mu    5.260
_exptl_absorpt_correction_T_max  0.5904
_exptl_absorpt_correction_T_min  0.1215
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
STOE LANA, absorption correction by scaling of reflection intensities.
J. Koziskova, F. Hahn, J. Richter, J. Kozisek, "Comparison of different
absorption corrections on the model structure of tetrakis(μ₂-acetato)-
diaqua-di-copper(II)", Acta Chimica Slovaca, vol. 9, no. 2, 2016, pp. 136 - 140.
Afterwards a spherical absorption correction was performed within STOE LANA.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_density_diffrn    2.168
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             848
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.217
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1449
_diffrn_reflns_av_unetI/netI     0.1026
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            17829
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.348
_diffrn_reflns_theta_min         3.145
_diffrn_ambient_temperature      100
_diffrn_detector                 'EIGER2 500K'
_diffrn_detector_area_resol_mean 13.33
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      '4040 frames, detector distance = 50 mm'
_diffrn_measurement_device       'Eulerian 4-circle diffractometer'
_diffrn_measurement_device_type  'STOE STADIVARI'
_diffrn_measurement_method       'rotation method, ω scans'
_diffrn_radiation_collimation    '1.2 0.6 mm diameter'
_diffrn_radiation_monochromator  'Graded multilayer mirror'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Axo Mo'
_diffrn_source_current           0.830
_diffrn_source_power             0.050
_diffrn_source_voltage           60
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1554
_reflns_number_total             2504
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
X-Area Recipe 2.0.2 (STOE, 2024)
;
_computing_data_collection       
;
X-Area Pilatus3_SV 1.31.194.0 (STOE, 2023)
;
_computing_data_reduction        
;
X-Area Integrate 2.5.15.0 (STOE, 2023)
X-Area X-Red 2.3.1.0 (STOE, 2023)
;
_computing_molecular_graphics    'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         2.063
_refine_diff_density_min         -2.121
_refine_diff_density_rms         0.291
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         2504
_refine_ls_number_restraints     46
_refine_ls_R_factor_all          0.1168
_refine_ls_R_factor_gt           0.0685
_refine_ls_restrained_S_all      1.007
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1306P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1725
_refine_ls_wR_factor_ref         0.2059
_refine_special_details          
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Rigid bond restraints
 F1, F2, C2, F3, C4
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
3. Uiso/Uaniso restraints and constraints
Uanis(C4) ∼ Ueq: with sigma of 0.003 and sigma for terminal atoms of 0.006
4. Rigid body (RIGU) restrains
 F1, F2, C2, F3, C4
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5.a Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B)
5.b Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C10(H10), C11(H11)
5.c Idealised Me refined as rotating group:
 C3(H3A,H3B,H3C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
I1 I 0.11369(6) 0.58225(7) 0.16335(10) 0.0357(3) Uani 1 1 d . . . . .
Br1 Br 0.62005(9) 0.14494(11) 0.35475(17) 0.0373(4) Uani 1 1 d . . . . .
F1 F 0.2179(6) 0.4813(6) 0.8239(8) 0.0413(19) Uani 1 1 d . U . . .
O1 O 0.1116(6) 0.4318(6) 0.5070(11) 0.034(2) Uani 1 1 d . . . . .
N1 N 0.1755(7) 0.3428(8) 0.4769(12) 0.028(2) Uani 1 1 d . . . . .
C1 C 0.2637(9) 0.3953(10) 0.4724(14) 0.028(3) Uani 1 1 d . . . . .
F2 F 0.2357(5) 0.6428(6) 0.7554(8) 0.0385(17) Uani 1 1 d . U . . .
N2 N 0.2683(7) 0.4976(8) 0.5089(12) 0.034(3) Uani 1 1 d . . . . .
C2 C 0.1735(9) 0.5267(11) 0.5358(14) 0.031(3) Uani 1 1 d . U . . .
F3 F 0.0941(6) 0.5851(6) 0.7478(8) 0.0426(19) Uani 1 1 d . U . . .
C3 C 0.1235(8) 0.2806(10) 0.3287(16) 0.036(3) Uani 1 1 d . . . . .
H3A H 0.061312 0.253715 0.350075 0.054 Uiso 1 1 calc R U . . .
H3B H 0.164022 0.219278 0.308542 0.054 Uiso 1 1 calc R U . . .
H3C H 0.110923 0.327903 0.229928 0.054 Uiso 1 1 calc R U . . .
C4 C 0.1898(9) 0.5679(9) 0.7348(14) 0.026(2) Uani 1 1 d . U . . .
C5 C 0.1270(10) 0.6207(11) 0.4218(16) 0.040(3) Uani 1 1 d . . . . .
H5A H 0.167751 0.686408 0.448953 0.048 Uiso 1 1 calc R U . . .
H5B H 0.061410 0.636664 0.443870 0.048 Uiso 1 1 calc R U . . .
C6 C 0.3478(8) 0.3336(9) 0.4463(13) 0.025(3) Uani 1 1 d . . . . .
C7 C 0.4250(9) 0.3873(10) 0.4049(15) 0.028(3) Uani 1 1 d . . . . .
H7 H 0.422714 0.463947 0.394533 0.034 Uiso 1 1 calc R U . . .
C8 C 0.5053(8) 0.3329(10) 0.3781(14) 0.029(3) Uani 1 1 d . . . . .
H8 H 0.558553 0.371915 0.351336 0.035 Uiso 1 1 calc R U . . .
C9 C 0.5096(8) 0.2194(10) 0.3899(13) 0.027(3) Uani 1 1 d . . . . .
C10 C 0.4343(9) 0.1634(10) 0.4398(14) 0.031(3) Uani 1 1 d . . . . .
H10 H 0.438245 0.086991 0.453042 0.037 Uiso 1 1 calc R U . . .
C11 C 0.3532(8) 0.2185(9) 0.4705(14) 0.026(3) Uani 1 1 d . . . . .
H11 H 0.302183 0.180664 0.506898 0.032 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
I1 C5 2.129(13) . ?
Br1 C9 1.870(12) . ?
F1 C4 1.306(12) . ?
O1 N1 1.469(12) . ?
O1 C2 1.445(14) . ?
N1 C1 1.400(15) . ?
N1 C3 1.486(14) . ?
C1 N2 1.295(14) . ?
C1 C6 1.454(16) . ?
F2 C4 1.118(13) . ?
N2 C2 1.434(16) . ?
C2 C4 1.669(16) . ?
C2 C5 1.543(17) . ?
F3 C4 1.381(14) . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C7 1.369(17) . ?
C6 C11 1.433(16) . ?
C7 H7 0.9500 . ?
C7 C8 1.364(16) . ?
C8 H8 0.9500 . ?
C8 C9 1.404(16) . ?
C9 C10 1.389(16) . ?
C10 H10 0.9500 . ?
C10 C11 1.389(16) . ?
C11 H11 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 O1 N1 105.6(8) . . ?
O1 N1 C3 108.1(8) . . ?
C1 N1 O1 103.2(8) . . ?
C1 N1 C3 120.1(10) . . ?
N1 C1 C6 120.3(10) . . ?
N2 C1 N1 116.5(11) . . ?
N2 C1 C6 122.8(11) . . ?
C1 N2 C2 106.0(10) . . ?
O1 C2 C4 111.2(10) . . ?
O1 C2 C5 110.4(9) . . ?
N2 C2 O1 108.2(10) . . ?
N2 C2 C4 106.4(9) . . ?
N2 C2 C5 112.6(11) . . ?
C5 C2 C4 108.1(10) . . ?
N1 C3 H3A 109.5 . . ?
N1 C3 H3B 109.5 . . ?
N1 C3 H3C 109.5 . . ?
H3A C3 H3B 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
F1 C4 C2 104.8(9) . . ?
F1 C4 F3 105.5(10) . . ?
F2 C4 F1 119.8(11) . . ?
F2 C4 C2 110.9(10) . . ?
F2 C4 F3 113.4(10) . . ?
F3 C4 C2 100.5(9) . . ?
I1 C5 H5A 109.3 . . ?
I1 C5 H5B 109.3 . . ?
C2 C5 I1 111.5(9) . . ?
C2 C5 H5A 109.3 . . ?
C2 C5 H5B 109.3 . . ?
H5A C5 H5B 108.0 . . ?
C7 C6 C1 119.1(11) . . ?
C7 C6 C11 119.5(11) . . ?
C11 C6 C1 121.3(11) . . ?
C6 C7 H7 119.4 . . ?
C8 C7 C6 121.3(11) . . ?
C8 C7 H7 119.4 . . ?
C7 C8 H8 119.8 . . ?
C7 C8 C9 120.3(12) . . ?
C9 C8 H8 119.8 . . ?
C8 C9 Br1 120.3(9) . . ?
C10 C9 Br1 120.1(9) . . ?
C10 C9 C8 119.4(11) . . ?
C9 C10 H10 119.8 . . ?
C11 C10 C9 120.4(11) . . ?
C11 C10 H10 119.8 . . ?
C6 C11 H11 120.6 . . ?
C10 C11 C6 118.8(11) . . ?
C10 C11 H11 120.6 . . ?

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
Br1 C9 C10 C11 178.3(8) . . . . ?
O1 N1 C1 N2 6.0(13) . . . . ?
O1 N1 C1 C6 179.3(9) . . . . ?
O1 C2 C4 F1 51.3(12) . . . . ?
O1 C2 C4 F2 -178.2(10) . . . . ?
O1 C2 C4 F3 -58.0(11) . . . . ?
O1 C2 C5 I1 -63.1(12) . . . . ?
N1 O1 C2 N2 5.0(11) . . . . ?
N1 O1 C2 C4 -111.4(10) . . . . ?
N1 O1 C2 C5 128.6(10) . . . . ?
N1 C1 N2 C2 -2.9(14) . . . . ?
N1 C1 C6 C7 165.4(11) . . . . ?
N1 C1 C6 C11 -17.4(16) . . . . ?
C1 N2 C2 O1 -1.5(12) . . . . ?
C1 N2 C2 C4 118.0(10) . . . . ?
C1 N2 C2 C5 -123.8(11) . . . . ?
C1 C6 C7 C8 -179.6(10) . . . . ?
C1 C6 C11 C10 178.5(10) . . . . ?
N2 C1 C6 C7 -21.7(17) . . . . ?
N2 C1 C6 C11 155.5(11) . . . . ?
N2 C2 C4 F1 -66.3(12) . . . . ?
N2 C2 C4 F2 64.2(13) . . . . ?
N2 C2 C4 F3 -175.6(9) . . . . ?
N2 C2 C5 I1 58.0(12) . . . . ?
C2 O1 N1 C1 -6.3(11) . . . . ?
C2 O1 N1 C3 -134.5(9) . . . . ?
C3 N1 C1 N2 126.3(11) . . . . ?
C3 N1 C1 C6 -60.4(15) . . . . ?
C4 C2 C5 I1 175.2(8) . . . . ?
C5 C2 C4 F1 172.6(10) . . . . ?
C5 C2 C4 F2 -56.9(13) . . . . ?
C5 C2 C4 F3 63.3(11) . . . . ?
C6 C1 N2 C2 -176.1(10) . . . . ?
C6 C7 C8 C9 1.1(17) . . . . ?
C7 C6 C11 C10 -4.4(16) . . . . ?
C7 C8 C9 Br1 -179.5(8) . . . . ?
C7 C8 C9 C10 -4.2(16) . . . . ?
C8 C9 C10 C11 2.9(16) . . . . ?
C9 C10 C11 C6 1.3(16) . . . . ?
C11 C6 C7 C8 3.2(17) . . . . ?

####################################################################### 
# 
# 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_dc716
_database_code_depnum_ccdc_archive 'CCDC 2493077'
loop_
_audit_author_name
_audit_author_address
'Alexander Prado-Roler'
;University of Vienna
Austria
;
_audit_update_record             
;
2025-10-03 deposited with the CCDC.	2026-01-08 downloaded from the CCDC.
;
_vrf_PLAT341_3b                  
;PROBLEM: Low Bond Precision on  C-C Bonds ...............      0.017 Ang. 
RESPONSE: we could not solve all the twinning effects. Also many spot positions 
are splittet very close and could not be seperated for the modelling and 
refinement workflow.
;
_vrf_PLAT971_2b                  
;PROBLEM: Check Calcd Resid. Dens.  1.83Ang From C11B            2.72 eA-3  
RESPONSE: At least three rest densities seem to be real densities. It is very 
likely that it is related to an unsolved twinning effect. 
;
_audit_creation_date             2025-07-29
_audit_creation_method           
;
Olex2 1.5-alpha
(compiled 2025.07.13 svn.rb7424aed for OlexSys, GUI svn.r7311)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C11 H9 Br Cl F3 N2 O)'
_chemical_formula_sum            'C11 H9 Br Cl F3 N2 O'
_chemical_formula_weight         357.56
_chemical_absolute_configuration ad
_chemical_melting_point          ?
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'
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'

_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.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   27.4602(8)
_cell_length_b                   12.7464(3)
_cell_length_c                   7.4938(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2622.97(12)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    114745
_cell_measurement_temperature    100
_cell_measurement_theta_max      30.89
_cell_measurement_theta_min      2.74
_shelx_estimated_absorpt_T_max   0.850
_shelx_estimated_absorpt_T_min   0.346
_exptl_absorpt_coefficient_mu    3.366
_exptl_absorpt_correction_T_max  0.3759
_exptl_absorpt_correction_T_min  0.2765
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
STOE LANA, absorption correction by scaling of reflection intensities.
J. Koziskova, F. Hahn, J. Richter, J. Kozisek, "Comparison of different
absorption corrections on the model structure of tetrakis(μ₂-acetato)-
diaqua-di-copper(II)", Acta Chimica Slovaca, vol. 9, no. 2, 2016, pp. 136 - 140.
Afterwards a spherical absorption correction was performed within STOE LANA.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_density_diffrn    1.811
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1408
_exptl_crystal_preparation       ?
_exptl_crystal_recrystallization_method ?
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0540
_diffrn_reflns_av_unetI/netI     0.0405
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_h_min       -33
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            38494
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.677
_diffrn_reflns_theta_min         2.740
_diffrn_ambient_temperature      100
_diffrn_detector                 'EIGER2 500K'
_diffrn_detector_area_resol_mean 13.33
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
 6911 frames, detector distance = 50 mm
;
_diffrn_measurement_device       'Eulerian 4-circle diffractometer'
_diffrn_measurement_device_type  'STOE STADIVARI'
_diffrn_measurement_method       'rotation method, ω scans'
_diffrn_radiation_collimation    '1.2 0.6 mm diameter'
_diffrn_radiation_monochromator  'Graded multilayer mirror'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Axo Mo'
_diffrn_source_current           0.830
_diffrn_source_power             0.050
_diffrn_source_voltage           60
_reflns_Friedel_coverage         0.744
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                4371
_reflns_number_total             4954
_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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
X-Area Recipe 2.0.2 (STOE, 2024)
;
_computing_data_collection       
;
X-Area Pilatus3_SV 1.31.194.0 (STOE, 2023)
;
_computing_data_reduction        
;
X-Area Integrate 2.5.18.0 (STOE, 2024)
X-Area X-Red 2.3.1.0 (STOE, 2023)
;
_computing_molecular_graphics    'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         2.404
_refine_diff_density_min         -0.795
_refine_diff_density_rms         0.169
_refine_ls_abs_structure_details 
;
 Refined as a perfect inversion twin.
;
_refine_ls_abs_structure_Flack   0.5
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     347
_refine_ls_number_reflns         4954
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0837
_refine_ls_R_factor_gt           0.0728
_refine_ls_restrained_S_all      1.079
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1215P)²+11.4787P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1870
_refine_ls_wR_factor_ref         0.1937
_refine_special_details          
;
 Refined as a 2-component perfect inversion twin.

1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C5B(H5BA,H5BB), C5A(H5AA,H5AB)
2.b Aromatic/amide H refined with riding coordinates:
 C7B(H7B), C8B(H8B), C10B(H10B), C11B(H11B), C7A(H7A), C8A(H8A), C10A(H10A),
 C11A(H11A)
2.c Idealised Me refined as rotating group:
 C3B(H3BA,H3BB,H3BC), C3A(H3AA,H3AB,H3AC)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
Br1B Br 0.43517(4) 0.48442(10) 0.29966(19) 0.0319(14) Uani 1 1 d . . . . .
Cl1B Cl 0.68644(10) 0.0460(2) 0.2893(4) 0.0229(15) Uani 1 1 d . . . . .
F1B F 0.6412(3) 0.0254(6) 0.8712(10) 0.039(2) Uani 1 1 d . . . . .
O1B O 0.6970(3) 0.2118(6) 0.5816(12) 0.026(2) Uani 1 1 d . . . . .
N1B N 0.6653(3) 0.2948(7) 0.5176(13) 0.021(2) Uani 1 1 d . . . . .
C1B C 0.6196(4) 0.2474(9) 0.5111(15) 0.018(3) Uani 1 1 d . . . . .
F2B F 0.6524(3) 0.1890(6) 0.9155(10) 0.039(2) Uani 1 1 d . . . . .
N2B N 0.6173(3) 0.1531(8) 0.5703(14) 0.024(3) Uani 1 1 d . . . . .
C2B C 0.6643(4) 0.1227(10) 0.6201(17) 0.026(3) Uani 1 1 d . . . . .
F3B F 0.7143(3) 0.0896(7) 0.8752(10) 0.041(2) Uani 1 1 d . . . . .
C3B C 0.6868(5) 0.3354(10) 0.3496(17) 0.027(3) Uani 1 1 d . . . . .
H3BA H 0.720989 0.353790 0.369880 0.041 Uiso 1 1 calc R U . . .
H3BB H 0.668830 0.397869 0.311118 0.041 Uiso 1 1 calc R U . . .
H3BC H 0.684721 0.281357 0.256899 0.041 Uiso 1 1 calc R U . . .
C4B C 0.6701(4) 0.1105(11) 0.8224(15) 0.027(3) Uani 1 1 d . . . . .
C5B C 0.6826(5) 0.0250(10) 0.5284(17) 0.027(3) Uani 1 1 d . . . . .
H5BA H 0.660170 -0.034013 0.553440 0.032 Uiso 1 1 calc R U . . .
H5BB H 0.715110 0.006448 0.575635 0.032 Uiso 1 1 calc R U . . .
C6B C 0.5762(4) 0.3083(10) 0.4520(15) 0.023(3) Uani 1 1 d . . . . .
C7B C 0.5356(4) 0.2528(10) 0.3964(16) 0.022(3) Uani 1 1 d . . . . .
H7B H 0.536968 0.178472 0.389511 0.026 Uiso 1 1 calc R U . . .
C8B C 0.4936(4) 0.3042(10) 0.3511(16) 0.025(3) Uani 1 1 d . . . . .
H8B H 0.465183 0.266670 0.317108 0.030 Uiso 1 1 calc R U . . .
C9B C 0.4941(4) 0.4142(9) 0.3566(14) 0.021(3) Uani 1 1 d . . . . .
C10B C 0.5335(5) 0.4717(10) 0.4061(17) 0.027(3) Uani 1 1 d . . . . .
H10B H 0.532481 0.546182 0.407755 0.032 Uiso 1 1 calc R U . . .
C11B C 0.5761(4) 0.4167(9) 0.4551(15) 0.022(3) Uani 1 1 d . . . . .
H11B H 0.604547 0.453959 0.489922 0.026 Uiso 1 1 calc R U . . .
Br1A Br 1.06130(4) 0.68067(10) 0.30971(19) 0.0347(14) Uani 1 1 d . . . . .
Cl1A Cl 0.81512(10) 0.2308(2) 0.2911(4) 0.0204(15) Uani 1 1 d . . . . .
F1A F 0.8549(3) 0.2234(6) 0.8831(10) 0.034(2) Uani 1 1 d . . . . .
O1A O 0.7994(3) 0.4012(6) 0.5756(11) 0.022(2) Uani 1 1 d . . . . .
N1A N 0.8305(3) 0.4858(8) 0.5084(15) 0.024(3) Uani 1 1 d . . . . .
C1A C 0.8764(4) 0.4415(10) 0.5110(16) 0.023(3) Uani 1 1 d . . . . .
F2A F 0.7817(3) 0.2812(6) 0.8730(10) 0.033(2) Uani 1 1 d . . . . .
N2A N 0.8804(3) 0.3485(7) 0.5784(13) 0.021(3) Uani 1 1 d . . . . .
C2A C 0.8314(4) 0.3173(9) 0.6219(16) 0.018(3) Uani 1 1 d . . . . .
F3A F 0.8405(3) 0.3889(6) 0.9115(10) 0.035(2) Uani 1 1 d . . . . .
C3A C 0.8098(5) 0.5205(11) 0.3405(16) 0.030(3) Uani 1 1 d . . . . .
H3AA H 0.810094 0.462373 0.255009 0.046 Uiso 1 1 calc R U . . .
H3AB H 0.829187 0.578847 0.293240 0.046 Uiso 1 1 calc R U . . .
H3AC H 0.776237 0.543913 0.359780 0.046 Uiso 1 1 calc R U . . .
C4A C 0.8264(4) 0.3005(11) 0.8258(19) 0.030(3) Uani 1 1 d . . . . .
C5A C 0.8163(4) 0.2128(9) 0.5307(16) 0.024(3) Uani 1 1 d . . . . .
H5AA H 0.783682 0.191235 0.573326 0.029 Uiso 1 1 calc R U . . .
H5AB H 0.839809 0.156924 0.562172 0.029 Uiso 1 1 calc R U . . .
C6A C 0.9192(4) 0.5011(9) 0.4539(14) 0.019(3) Uani 1 1 d . . . . .
C7A C 0.9196(5) 0.6113(9) 0.4568(14) 0.022(3) Uani 1 1 d . . . . .
H7A H 0.891402 0.649574 0.490824 0.026 Uiso 1 1 calc R U . . .
C8A C 0.9619(5) 0.6626(10) 0.4092(18) 0.030(3) Uani 1 1 d . . . . .
H8A H 0.962424 0.737101 0.407876 0.036 Uiso 1 1 calc R U . . .
C9A C 1.0026(4) 0.6091(11) 0.3644(15) 0.027(3) Uani 1 1 d . . . . .
C10A C 1.0036(4) 0.5011(10) 0.3578(15) 0.024(3) Uani 1 1 d . . . . .
H10A H 1.032334 0.464658 0.324197 0.029 Uiso 1 1 calc R U . . .
C11A C 0.9609(4) 0.4467(9) 0.4020(16) 0.021(3) Uani 1 1 d . . . . .
H11A H 0.960379 0.372277 0.396551 0.025 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
Br1B C9B 1.897(11) . ?
Cl1B C5B 1.815(13) . ?
F1B C4B 1.393(17) . ?
O1B N1B 1.451(12) . ?
O1B C2B 1.475(14) . ?
N1B C1B 1.392(14) . ?
N1B C3B 1.484(15) . ?
C1B N2B 1.282(15) . ?
C1B C6B 1.491(16) . ?
F2B C4B 1.313(14) . ?
N2B C2B 1.398(16) . ?
C2B C4B 1.532(16) . ?
C2B C5B 1.508(19) . ?
F3B C4B 1.303(14) . ?
C3B H3BA 0.9800 . ?
C3B H3BB 0.9800 . ?
C3B H3BC 0.9800 . ?
C5B H5BA 0.9900 . ?
C5B H5BB 0.9900 . ?
C6B C7B 1.384(17) . ?
C6B C11B 1.381(17) . ?
C7B H7B 0.9500 . ?
C7B C8B 1.370(17) . ?
C8B H8B 0.9500 . ?
C8B C9B 1.403(18) . ?
C9B C10B 1.360(18) . ?
C10B H10B 0.9500 . ?
C10B C11B 1.412(17) . ?
C11B H11B 0.9500 . ?
Br1A C9A 1.898(11) . ?
Cl1A C5A 1.811(12) . ?
F1A C4A 1.328(14) . ?
O1A N1A 1.464(12) . ?
O1A C2A 1.426(13) . ?
N1A C1A 1.382(15) . ?
N1A C3A 1.449(16) . ?
C1A N2A 1.294(17) . ?
C1A C6A 1.461(17) . ?
F2A C4A 1.299(15) . ?
N2A C2A 1.441(14) . ?
C2A C4A 1.549(18) . ?
C2A C5A 1.553(16) . ?
F3A C4A 1.354(16) . ?
C3A H3AA 0.9800 . ?
C3A H3AB 0.9800 . ?
C3A H3AC 0.9800 . ?
C5A H5AA 0.9900 . ?
C5A H5AB 0.9900 . ?
C6A C7A 1.405(17) . ?
C6A C11A 1.394(16) . ?
C7A H7A 0.9500 . ?
C7A C8A 1.380(18) . ?
C8A H8A 0.9500 . ?
C8A C9A 1.35(2) . ?
C9A C10A 1.38(2) . ?
C10A H10A 0.9500 . ?
C10A C11A 1.402(16) . ?
C11A H11A 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
N1B O1B C2B 105.2(8) . . ?
O1B N1B C3B 107.2(9) . . ?
C1B N1B O1B 103.6(8) . . ?
C1B N1B C3B 118.7(10) . . ?
N1B C1B C6B 120.3(10) . . ?
N2B C1B N1B 116.0(10) . . ?
N2B C1B C6B 123.5(11) . . ?
C1B N2B C2B 107.8(10) . . ?
O1B C2B C4B 102.0(11) . . ?
O1B C2B C5B 110.1(10) . . ?
N2B C2B O1B 107.2(10) . . ?
N2B C2B C4B 112.9(10) . . ?
N2B C2B C5B 114.5(11) . . ?
C5B C2B C4B 109.4(11) . . ?
N1B C3B H3BA 109.5 . . ?
N1B C3B H3BB 109.5 . . ?
N1B C3B H3BC 109.5 . . ?
H3BA C3B H3BB 109.5 . . ?
H3BA C3B H3BC 109.5 . . ?
H3BB C3B H3BC 109.5 . . ?
F1B C4B C2B 106.2(11) . . ?
F2B C4B F1B 104.1(9) . . ?
F2B C4B C2B 114.2(11) . . ?
F3B C4B F1B 106.9(10) . . ?
F3B C4B F2B 109.8(11) . . ?
F3B C4B C2B 114.7(10) . . ?
Cl1B C5B H5BA 109.6 . . ?
Cl1B C5B H5BB 109.6 . . ?
C2B C5B Cl1B 110.4(9) . . ?
C2B C5B H5BA 109.6 . . ?
C2B C5B H5BB 109.6 . . ?
H5BA C5B H5BB 108.1 . . ?
C7B C6B C1B 117.8(11) . . ?
C11B C6B C1B 121.1(11) . . ?
C11B C6B C7B 121.0(12) . . ?
C6B C7B H7B 119.7 . . ?
C8B C7B C6B 120.6(11) . . ?
C8B C7B H7B 119.7 . . ?
C7B C8B H8B 121.2 . . ?
C7B C8B C9B 117.6(12) . . ?
C9B C8B H8B 121.2 . . ?
C8B C9B Br1B 117.2(9) . . ?
C10B C9B Br1B 119.1(9) . . ?
C10B C9B C8B 123.6(11) . . ?
C9B C10B H10B 121.2 . . ?
C9B C10B C11B 117.6(11) . . ?
C11B C10B H10B 121.2 . . ?
C6B C11B C10B 119.5(12) . . ?
C6B C11B H11B 120.2 . . ?
C10B C11B H11B 120.2 . . ?
C2A O1A N1A 106.1(8) . . ?
C1A N1A O1A 103.0(9) . . ?
C1A N1A C3A 119.6(11) . . ?
C3A N1A O1A 107.2(9) . . ?
N1A C1A C6A 121.1(11) . . ?
N2A C1A N1A 117.2(11) . . ?
N2A C1A C6A 121.5(11) . . ?
C1A N2A C2A 105.2(9) . . ?
O1A C2A N2A 108.2(9) . . ?
O1A C2A C4A 106.8(9) . . ?
O1A C2A C5A 111.8(9) . . ?
N2A C2A C4A 110.2(9) . . ?
N2A C2A C5A 112.7(9) . . ?
C4A C2A C5A 107.0(10) . . ?
N1A C3A H3AA 109.5 . . ?
N1A C3A H3AB 109.5 . . ?
N1A C3A H3AC 109.5 . . ?
H3AA C3A H3AB 109.5 . . ?
H3AA C3A H3AC 109.5 . . ?
H3AB C3A H3AC 109.5 . . ?
F1A C4A C2A 111.6(11) . . ?
F1A C4A F3A 107.0(10) . . ?
F2A C4A F1A 109.2(11) . . ?
F2A C4A C2A 112.3(11) . . ?
F2A C4A F3A 107.4(11) . . ?
F3A C4A C2A 109.1(11) . . ?
Cl1A C5A H5AA 109.8 . . ?
Cl1A C5A H5AB 109.8 . . ?
C2A C5A Cl1A 109.4(8) . . ?
C2A C5A H5AA 109.8 . . ?
C2A C5A H5AB 109.8 . . ?
H5AA C5A H5AB 108.2 . . ?
C7A C6A C1A 121.4(11) . . ?
C11A C6A C1A 118.9(10) . . ?
C11A C6A C7A 119.6(11) . . ?
C6A C7A H7A 120.8 . . ?
C8A C7A C6A 118.5(12) . . ?
C8A C7A H7A 120.8 . . ?
C7A C8A H8A 119.3 . . ?
C9A C8A C7A 121.4(12) . . ?
C9A C8A H8A 119.3 . . ?
C8A C9A Br1A 120.9(10) . . ?
C8A C9A C10A 122.0(11) . . ?
C10A C9A Br1A 117.1(10) . . ?
C9A C10A H10A 121.0 . . ?
C9A C10A C11A 117.9(12) . . ?
C11A C10A H10A 121.0 . . ?
C6A C11A C10A 120.5(11) . . ?
C6A C11A H11A 119.7 . . ?
C10A C11A H11A 119.7 . . ?

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
Br1B C9B C10B C11B 177.3(8) . . . . ?
O1B N1B C1B N2B 4.4(13) . . . . ?
O1B N1B C1B C6B 179.5(9) . . . . ?
O1B C2B C4B F1B -178.5(8) . . . . ?
O1B C2B C4B F2B 67.4(13) . . . . ?
O1B C2B C4B F3B -60.6(15) . . . . ?
O1B C2B C5B Cl1B -58.4(12) . . . . ?
N1B O1B C2B N2B 3.1(13) . . . . ?
N1B O1B C2B C4B -115.7(9) . . . . ?
N1B O1B C2B C5B 128.2(10) . . . . ?
N1B C1B N2B C2B -2.5(14) . . . . ?
N1B C1B C6B C7B 160.9(11) . . . . ?
N1B C1B C6B C11B -20.0(17) . . . . ?
C1B N2B C2B O1B -0.6(13) . . . . ?
C1B N2B C2B C4B 111.0(13) . . . . ?
C1B N2B C2B C5B -123.0(11) . . . . ?
C1B C6B C7B C8B 175.9(11) . . . . ?
C1B C6B C11B C10B -177.0(10) . . . . ?
N2B C1B C6B C7B -24.4(17) . . . . ?
N2B C1B C6B C11B 154.7(12) . . . . ?
N2B C2B C4B F1B 66.8(13) . . . . ?
N2B C2B C4B F2B -47.3(17) . . . . ?
N2B C2B C4B F3B -175.3(11) . . . . ?
N2B C2B C5B Cl1B 62.5(12) . . . . ?
C2B O1B N1B C1B -4.3(12) . . . . ?
C2B O1B N1B C3B -130.5(10) . . . . ?
C3B N1B C1B N2B 123.0(11) . . . . ?
C3B N1B C1B C6B -61.8(14) . . . . ?
C4B C2B C5B Cl1B -169.7(9) . . . . ?
C5B C2B C4B F1B -61.9(12) . . . . ?
C5B C2B C4B F2B -176.0(10) . . . . ?
C5B C2B C4B F3B 56.0(16) . . . . ?
C6B C1B N2B C2B -177.4(11) . . . . ?
C6B C7B C8B C9B 2.5(18) . . . . ?
C7B C6B C11B C10B 2.0(18) . . . . ?
C7B C8B C9B Br1B -178.4(8) . . . . ?
C7B C8B C9B C10B -0.8(19) . . . . ?
C8B C9B C10B C11B -0.3(19) . . . . ?
C9B C10B C11B C6B -0.3(18) . . . . ?
C11B C6B C7B C8B -3.1(18) . . . . ?
Br1A C9A C10A C11A 178.5(8) . . . . ?
O1A N1A C1A N2A -4.7(14) . . . . ?
O1A N1A C1A C6A -179.6(10) . . . . ?
O1A C2A C4A F1A -179.9(9) . . . . ?
O1A C2A C4A F2A 57.1(14) . . . . ?
O1A C2A C4A F3A -61.9(12) . . . . ?
O1A C2A C5A Cl1A 57.5(11) . . . . ?
N1A O1A C2A N2A -1.9(12) . . . . ?
N1A O1A C2A C4A 116.7(10) . . . . ?
N1A O1A C2A C5A -126.7(9) . . . . ?
N1A C1A N2A C2A 3.5(14) . . . . ?
N1A C1A C6A C7A 23.6(17) . . . . ?
N1A C1A C6A C11A -158.9(11) . . . . ?
C1A N2A C2A O1A -0.8(12) . . . . ?
C1A N2A C2A C4A -117.2(11) . . . . ?
C1A N2A C2A C5A 123.5(10) . . . . ?
C1A C6A C7A C8A 177.0(11) . . . . ?
C1A C6A C11A C10A -175.8(11) . . . . ?
N2A C1A C6A C7A -151.2(12) . . . . ?
N2A C1A C6A C11A 26.4(16) . . . . ?
N2A C2A C4A F1A -62.6(14) . . . . ?
N2A C2A C4A F2A 174.4(10) . . . . ?
N2A C2A C4A F3A 55.5(13) . . . . ?
N2A C2A C5A Cl1A -64.7(10) . . . . ?
C2A O1A N1A C1A 3.7(11) . . . . ?
C2A O1A N1A C3A 130.7(10) . . . . ?
C3A N1A C1A N2A -123.4(12) . . . . ?
C3A N1A C1A C6A 61.6(16) . . . . ?
C4A C2A C5A Cl1A 174.0(8) . . . . ?
C5A C2A C4A F1A 60.2(13) . . . . ?
C5A C2A C4A F2A -62.8(13) . . . . ?
C5A C2A C4A F3A 178.3(9) . . . . ?
C6A C1A N2A C2A 178.5(10) . . . . ?
C6A C7A C8A C9A -1.5(18) . . . . ?
C7A C6A C11A C10A 1.8(17) . . . . ?
C7A C8A C9A Br1A -177.1(9) . . . . ?
C7A C8A C9A C10A 2(2) . . . . ?
C8A C9A C10A C11A -1.0(19) . . . . ?
C9A C10A C11A C6A -1.1(17) . . . . ?
C11A C6A C7A C8A -0.6(17) . . . . ?

####################################################################### 
# 
# 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_dc757
_database_code_depnum_ccdc_archive 'CCDC 2493081'
loop_
_audit_author_name
_audit_author_address
'Alexander Prado-Roler'
;University of Vienna
Austria
;
_audit_update_record             
;
2025-10-03 deposited with the CCDC.	2026-01-08 downloaded from the CCDC.
;
_audit_creation_date             2025-07-07
_audit_creation_method           
;
Olex2 1.5-alpha
(compiled 2025.07.01 svn.ra095ee60 for OlexSys, GUI svn.r7302)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H13 Br F3 N2 O'
_chemical_formula_sum            'C12 H12 Br F3 N2 O'
_chemical_formula_weight         337.15
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   9.5398(6)
_cell_length_b                   14.6986(7)
_cell_length_c                   19.7485(14)
_cell_angle_alpha                90
_cell_angle_beta                 103.711(5)
_cell_angle_gamma                90
_cell_volume                     2690.3(3)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    46153
_cell_measurement_temperature    100
_cell_measurement_theta_max      27.66
_cell_measurement_theta_min      2.67
_shelx_estimated_absorpt_T_max   0.748
_shelx_estimated_absorpt_T_min   0.458
_exptl_absorpt_coefficient_mu    3.084
_exptl_absorpt_correction_T_max  0.7594
_exptl_absorpt_correction_T_min  0.5386
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
STOE LANA, absorption correction by scaling of reflection intensities.
J. Koziskova, F. Hahn, J. Richter, J. Kozisek, "Comparison of different
absorption corrections on the model structure of tetrakis(μ₂-acetato)-
diaqua-di-copper(II)", Acta Chimica Slovaca, vol. 9, no. 2, 2016, pp. 136 - 140.
Afterwards a spherical absorption correction was performed within STOE LANA.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_density_diffrn    1.665
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1344
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.233
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0793
_diffrn_reflns_av_unetI/netI     0.0971
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            52144
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.347
_diffrn_reflns_theta_min         2.772
_diffrn_ambient_temperature      100
_diffrn_detector                 'EIGER2 500K'
_diffrn_detector_area_resol_mean 13.33
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      '5761 frames, detector distance = 50 mm'
_diffrn_measurement_device       'Eulerian 4-circle diffractometer'
_diffrn_measurement_device_type  'STOE STADIVARI'
_diffrn_measurement_method       'rotation method, ω scans'
_diffrn_radiation_collimation    '1.2 0.6 mm diameter'
_diffrn_radiation_monochromator  'Graded multilayer mirror'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Axo Mo'
_diffrn_source_current           0.830
_diffrn_source_power             0.050
_diffrn_source_voltage           60
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2993
_reflns_number_total             4922
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
X-Area Recipe 2.0.1 (STOE, 2023)
;
_computing_data_collection       
;
X-Area Pilatus3_SV 1.31.192.0 (STOE, 2023)
;
_computing_data_reduction        
;
X-Area Integrate 2.5.15.0 (STOE, 2023)
X-Area LANA 2.7.12 (STOE, 2023)
;
_computing_molecular_graphics    'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.863
_refine_diff_density_min         -0.714
_refine_diff_density_rms         0.141
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.007
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     347
_refine_ls_number_reflns         4922
_refine_ls_number_restraints     10
_refine_ls_R_factor_all          0.0842
_refine_ls_R_factor_gt           0.0490
_refine_ls_restrained_S_all      1.007
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0832P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1402
_refine_ls_wR_factor_ref         0.1471
_refine_special_details          
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Rigid bond restraints
 C4B, C2B, F2B, F3B, F1B
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
3.a Secondary CH2 refined with riding coordinates:
 C5A(H5AA,H5AB), C5B(H5BA,H5BB)
3.b Aromatic/amide H refined with riding coordinates:
 C7A(H7A), C9A(H9A), C10A(H10A), C11A(H11A), C7B(H7B), C9B(H9B), C10B(H10B),
 C11B(H11B)
3.c Idealised Me refined as rotating group:
 C3A(H3AA,H3AB,H3AC), C12A(H12A,H12B,H12C), C3B(H3BA,H3BB,H3BC), C12B(H12D,
 H12E,H12F)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
Br1A Br 0.14558(7) 0.41073(3) 0.02378(3) 0.02109(19) Uani 1 1 d . . . . .
F1A F 0.2858(5) 0.1028(2) 0.1684(2) 0.0475(11) Uani 1 1 d . . . . .
O1A O 0.3615(5) 0.2720(3) 0.1312(3) 0.0413(13) Uani 1 1 d . . . . .
N1A N 0.3597(6) 0.3115(3) 0.1992(3) 0.0405(16) Uani 1 1 d . . . . .
C1A C 0.2134(7) 0.3043(4) 0.2020(4) 0.0336(18) Uani 1 1 d . . . . .
F2A F 0.1060(5) 0.0939(2) 0.0794(3) 0.0532(13) Uani 1 1 d . . . . .
N2A N 0.1283(6) 0.2617(3) 0.1503(3) 0.0371(15) Uani 1 1 d . . . . .
C2A C 0.2172(7) 0.2374(4) 0.1032(4) 0.0325(18) Uani 1 1 d . . . . .
F3A F 0.3209(5) 0.1060(2) 0.0649(3) 0.0515(12) Uani 1 1 d . . . . .
C3A C 0.4225(8) 0.4021(4) 0.2019(5) 0.049(2) Uani 1 1 d . . . . .
H3AA H 0.362471 0.440283 0.165691 0.074 Uiso 1 1 calc R U . . .
H3AB H 0.519949 0.397810 0.193999 0.074 Uiso 1 1 calc R U . . .
H3AC H 0.427448 0.429105 0.247748 0.074 Uiso 1 1 calc R U . . .
C4A C 0.2310(8) 0.1345(4) 0.1038(4) 0.0345(18) Uani 1 1 d . . . . .
C5A C 0.1577(8) 0.2707(4) 0.0286(4) 0.0397(19) Uani 1 1 d . . . . .
H5AA H 0.060352 0.244740 0.010223 0.048 Uiso 1 1 calc R U . . .
H5AB H 0.220866 0.248964 -0.001253 0.048 Uiso 1 1 calc R U . . .
C6A C 0.1671(8) 0.3376(4) 0.2643(4) 0.0357(18) Uani 1 1 d . . . . .
C7A C 0.0208(7) 0.3503(4) 0.2596(4) 0.0353(18) Uani 1 1 d . . . . .
H7A H -0.045578 0.339902 0.216166 0.042 Uiso 1 1 calc R U . . .
C8A C -0.0308(8) 0.3771(4) 0.3153(4) 0.0364(19) Uani 1 1 d . . . . .
C9A C 0.0654(9) 0.3922(4) 0.3769(4) 0.045(2) Uani 1 1 d . . . . .
H9A H 0.030741 0.410715 0.416097 0.054 Uiso 1 1 calc R U . . .
C10A C 0.2178(10) 0.3812(4) 0.3847(4) 0.051(2) Uani 1 1 d . . . . .
H10A H 0.283395 0.394063 0.427911 0.062 Uiso 1 1 calc R U . . .
C11A C 0.2671(9) 0.3517(4) 0.3286(4) 0.042(2) Uani 1 1 d . . . . .
H11A H 0.367016 0.340976 0.332938 0.051 Uiso 1 1 calc R U . . .
C12A C -0.1890(8) 0.3910(4) 0.3067(4) 0.046(2) Uani 1 1 d . . . . .
H12A H -0.241150 0.337018 0.285030 0.070 Uiso 1 1 calc R U . . .
H12B H -0.220178 0.444175 0.276995 0.070 Uiso 1 1 calc R U . . .
H12C H -0.209496 0.401086 0.352468 0.070 Uiso 1 1 calc R U . . .
Br1B Br 0.26231(7) 0.89491(4) 0.42130(4) 0.0267(2) Uani 1 1 d . . . . .
F1B F 0.3931(5) 0.5917(2) 0.5684(2) 0.0493(11) Uani 1 1 d . U . . .
O1B O 0.4742(5) 0.7573(3) 0.5282(3) 0.0417(13) Uani 1 1 d . . . . .
N1B N 0.4772(6) 0.7992(3) 0.5949(3) 0.0372(15) Uani 1 1 d . . . . .
C1B C 0.3341(7) 0.7994(4) 0.5982(4) 0.0311(17) Uani 1 1 d . . . . .
F2B F 0.2010(5) 0.5857(2) 0.4849(2) 0.0536(12) Uani 1 1 d . U . . .
N2B N 0.2444(6) 0.7579(3) 0.5487(3) 0.0397(16) Uani 1 1 d . . . . .
C2B C 0.3286(7) 0.7264(4) 0.5021(4) 0.0352(17) Uani 1 1 d . U . . .
F3B F 0.4113(5) 0.5875(2) 0.4624(3) 0.0555(13) Uani 1 1 d . U . . .
C3B C 0.5537(8) 0.8858(4) 0.5976(4) 0.049(2) Uani 1 1 d . . . . .
H3BA H 0.500133 0.926292 0.561135 0.074 Uiso 1 1 calc R U . . .
H3BB H 0.650377 0.875092 0.590298 0.074 Uiso 1 1 calc R U . . .
H3BC H 0.561725 0.914079 0.643344 0.074 Uiso 1 1 calc R U . . .
C4B C 0.3308(8) 0.6184(4) 0.5031(4) 0.0331(17) Uani 1 1 d . U . . .
C5B C 0.2709(8) 0.7570(4) 0.4271(4) 0.044(2) Uani 1 1 d . . . . .
H5BA H 0.173112 0.731522 0.408922 0.053 Uiso 1 1 calc R U . . .
H5BB H 0.334258 0.733640 0.397947 0.053 Uiso 1 1 calc R U . . .
C6B C 0.2915(7) 0.8371(4) 0.6599(4) 0.0306(17) Uani 1 1 d . . . . .
C7B C 0.1483(8) 0.8555(4) 0.6554(4) 0.0373(19) Uani 1 1 d . . . . .
H7B H 0.079119 0.846631 0.612650 0.045 Uiso 1 1 calc R U . . .
C8B C 0.1036(8) 0.8880(4) 0.7153(4) 0.0367(19) Uani 1 1 d . . . . .
C9B C 0.2054(8) 0.9011(4) 0.7766(4) 0.0352(18) Uani 1 1 d . . . . .
H9B H 0.176466 0.923778 0.816268 0.042 Uiso 1 1 calc R U . . .
C10B C 0.3475(8) 0.8820(4) 0.7813(4) 0.0388(19) Uani 1 1 d . . . . .
H10B H 0.416555 0.891793 0.824027 0.047 Uiso 1 1 calc R U . . .
C11B C 0.3917(8) 0.8481(4) 0.7237(4) 0.0363(18) Uani 1 1 d . . . . .
H11B H 0.490022 0.832584 0.727757 0.044 Uiso 1 1 calc R U . . .
C12B C -0.0579(8) 0.9065(4) 0.7078(4) 0.047(2) Uani 1 1 d . . . . .
H12D H -0.114801 0.861701 0.676000 0.070 Uiso 1 1 calc R U . . .
H12E H -0.081365 0.967797 0.689046 0.070 Uiso 1 1 calc R U . . .
H12F H -0.080513 0.901725 0.753550 0.070 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
Br1A C5A 2.062(6) . ?
F1A C4A 1.342(8) . ?
O1A N1A 1.467(7) . ?
O1A C2A 1.449(7) . ?
N1A C1A 1.414(8) . ?
N1A C3A 1.456(7) . ?
C1A N2A 1.305(8) . ?
C1A C6A 1.485(9) . ?
F2A C4A 1.318(8) . ?
N2A C2A 1.444(8) . ?
C2A C4A 1.518(8) . ?
C2A C5A 1.529(9) . ?
F3A C4A 1.346(7) . ?
C3A H3AA 0.9800 . ?
C3A H3AB 0.9800 . ?
C3A H3AC 0.9800 . ?
C5A H5AA 0.9900 . ?
C5A H5AB 0.9900 . ?
C6A C7A 1.389(9) . ?
C6A C11A 1.410(10) . ?
C7A H7A 0.9500 . ?
C7A C8A 1.366(9) . ?
C8A C9A 1.358(10) . ?
C8A C12A 1.492(10) . ?
C9A H9A 0.9500 . ?
C9A C10A 1.434(11) . ?
C10A H10A 0.9500 . ?
C10A C11A 1.373(10) . ?
C11A H11A 0.9500 . ?
C12A H12A 0.9800 . ?
C12A H12B 0.9800 . ?
C12A H12C 0.9800 . ?
Br1B C5B 2.031(6) . ?
F1B C4B 1.345(8) . ?
O1B N1B 1.448(7) . ?
O1B C2B 1.436(8) . ?
N1B C1B 1.383(8) . ?
N1B C3B 1.462(8) . ?
C1B N2B 1.290(8) . ?
C1B C6B 1.481(9) . ?
F2B C4B 1.297(8) . ?
N2B C2B 1.433(8) . ?
C2B C4B 1.588(9) . ?
C2B C5B 1.520(10) . ?
F3B C4B 1.317(7) . ?
C3B H3BA 0.9800 . ?
C3B H3BB 0.9800 . ?
C3B H3BC 0.9800 . ?
C5B H5BA 0.9900 . ?
C5B H5BB 0.9900 . ?
C6B C7B 1.375(8) . ?
C6B C11B 1.398(9) . ?
C7B H7B 0.9500 . ?
C7B C8B 1.430(9) . ?
C8B C9B 1.374(10) . ?
C8B C12B 1.537(9) . ?
C9B H9B 0.9500 . ?
C9B C10B 1.366(9) . ?
C10B H10B 0.9500 . ?
C10B C11B 1.397(9) . ?
C11B H11B 0.9500 . ?
C12B H12D 0.9800 . ?
C12B H12E 0.9800 . ?
C12B H12F 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2A O1A N1A 105.8(5) . . ?
C1A N1A O1A 103.4(5) . . ?
C1A N1A C3A 117.9(5) . . ?
C3A N1A O1A 107.5(5) . . ?
N1A C1A C6A 119.9(6) . . ?
N2A C1A N1A 116.2(6) . . ?
N2A C1A C6A 123.7(6) . . ?
C1A N2A C2A 105.8(6) . . ?
O1A C2A C4A 105.9(5) . . ?
O1A C2A C5A 110.9(6) . . ?
N2A C2A O1A 108.4(6) . . ?
N2A C2A C4A 107.8(5) . . ?
N2A C2A C5A 113.6(6) . . ?
C4A C2A C5A 109.8(6) . . ?
N1A C3A H3AA 109.5 . . ?
N1A C3A H3AB 109.5 . . ?
N1A C3A H3AC 109.5 . . ?
H3AA C3A H3AB 109.5 . . ?
H3AA C3A H3AC 109.5 . . ?
H3AB C3A H3AC 109.5 . . ?
F1A C4A C2A 111.5(6) . . ?
F1A C4A F3A 106.1(6) . . ?
F2A C4A F1A 107.8(6) . . ?
F2A C4A C2A 112.2(6) . . ?
F2A C4A F3A 107.2(6) . . ?
F3A C4A C2A 111.8(6) . . ?
Br1A C5A H5AA 109.3 . . ?
Br1A C5A H5AB 109.3 . . ?
C2A C5A Br1A 111.6(4) . . ?
C2A C5A H5AA 109.3 . . ?
C2A C5A H5AB 109.3 . . ?
H5AA C5A H5AB 108.0 . . ?
C7A C6A C1A 118.7(7) . . ?
C7A C6A C11A 119.7(7) . . ?
C11A C6A C1A 121.5(7) . . ?
C6A C7A H7A 118.9 . . ?
C8A C7A C6A 122.2(7) . . ?
C8A C7A H7A 118.9 . . ?
C7A C8A C12A 119.7(7) . . ?
C9A C8A C7A 118.3(7) . . ?
C9A C8A C12A 122.0(7) . . ?
C8A C9A H9A 119.0 . . ?
C8A C9A C10A 122.0(7) . . ?
C10A C9A H9A 119.0 . . ?
C9A C10A H10A 120.6 . . ?
C11A C10A C9A 118.8(8) . . ?
C11A C10A H10A 120.6 . . ?
C6A C11A H11A 120.5 . . ?
C10A C11A C6A 119.0(8) . . ?
C10A C11A H11A 120.5 . . ?
C8A C12A H12A 109.5 . . ?
C8A C12A H12B 109.5 . . ?
C8A C12A H12C 109.5 . . ?
H12A C12A H12B 109.5 . . ?
H12A C12A H12C 109.5 . . ?
H12B C12A H12C 109.5 . . ?
C2B O1B N1B 105.7(5) . . ?
O1B N1B C3B 107.8(5) . . ?
C1B N1B O1B 103.7(5) . . ?
C1B N1B C3B 119.1(5) . . ?
N1B C1B C6B 120.4(6) . . ?
N2B C1B N1B 116.6(6) . . ?
N2B C1B C6B 122.6(6) . . ?
C1B N2B C2B 105.5(6) . . ?
O1B C2B C4B 107.7(5) . . ?
O1B C2B C5B 110.6(6) . . ?
N2B C2B O1B 108.0(5) . . ?
N2B C2B C4B 108.8(5) . . ?
N2B C2B C5B 113.7(6) . . ?
C5B C2B C4B 107.9(6) . . ?
N1B C3B H3BA 109.5 . . ?
N1B C3B H3BB 109.5 . . ?
N1B C3B H3BC 109.5 . . ?
H3BA C3B H3BB 109.5 . . ?
H3BA C3B H3BC 109.5 . . ?
H3BB C3B H3BC 109.5 . . ?
F1B C4B C2B 107.7(6) . . ?
F2B C4B F1B 109.5(6) . . ?
F2B C4B C2B 111.0(5) . . ?
F2B C4B F3B 111.0(6) . . ?
F3B C4B F1B 107.2(6) . . ?
F3B C4B C2B 110.2(6) . . ?
Br1B C5B H5BA 109.5 . . ?
Br1B C5B H5BB 109.5 . . ?
C2B C5B Br1B 110.5(5) . . ?
C2B C5B H5BA 109.5 . . ?
C2B C5B H5BB 109.5 . . ?
H5BA C5B H5BB 108.1 . . ?
C7B C6B C1B 118.9(7) . . ?
C7B C6B C11B 119.4(7) . . ?
C11B C6B C1B 121.5(6) . . ?
C6B C7B H7B 120.0 . . ?
C6B C7B C8B 119.9(7) . . ?
C8B C7B H7B 120.0 . . ?
C7B C8B C12B 117.9(7) . . ?
C9B C8B C7B 119.2(7) . . ?
C9B C8B C12B 122.9(7) . . ?
C8B C9B H9B 119.6 . . ?
C10B C9B C8B 120.9(7) . . ?
C10B C9B H9B 119.6 . . ?
C9B C10B H10B 119.9 . . ?
C9B C10B C11B 120.3(7) . . ?
C11B C10B H10B 119.9 . . ?
C6B C11B H11B 119.9 . . ?
C10B C11B C6B 120.1(7) . . ?
C10B C11B H11B 119.9 . . ?
C8B C12B H12D 109.5 . . ?
C8B C12B H12E 109.5 . . ?
C8B C12B H12F 109.5 . . ?
H12D C12B H12E 109.5 . . ?
H12D C12B H12F 109.5 . . ?
H12E C12B H12F 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1A N1A C1A N2A 4.8(7) . . . . ?
O1A N1A C1A C6A 179.9(5) . . . . ?
O1A C2A C4A F1A 58.9(7) . . . . ?
O1A C2A C4A F2A 179.9(6) . . . . ?
O1A C2A C4A F3A -59.7(8) . . . . ?
O1A C2A C5A Br1A -60.6(6) . . . . ?
N1A O1A C2A N2A 4.4(6) . . . . ?
N1A O1A C2A C4A -111.1(5) . . . . ?
N1A O1A C2A C5A 129.8(5) . . . . ?
N1A C1A N2A C2A -2.1(8) . . . . ?
N1A C1A C6A C7A 164.8(6) . . . . ?
N1A C1A C6A C11A -18.8(9) . . . . ?
C1A N2A C2A O1A -1.6(7) . . . . ?
C1A N2A C2A C4A 112.6(6) . . . . ?
C1A N2A C2A C5A -125.5(6) . . . . ?
C1A C6A C7A C8A 177.2(6) . . . . ?
C1A C6A C11A C10A -178.9(6) . . . . ?
N2A C1A C6A C7A -20.5(9) . . . . ?
N2A C1A C6A C11A 156.0(6) . . . . ?
N2A C2A C4A F1A -57.0(7) . . . . ?
N2A C2A C4A F2A 64.0(8) . . . . ?
N2A C2A C4A F3A -175.6(6) . . . . ?
N2A C2A C5A Br1A 61.9(6) . . . . ?
C2A O1A N1A C1A -5.2(6) . . . . ?
C2A O1A N1A C3A -130.7(6) . . . . ?
C3A N1A C1A N2A 123.3(7) . . . . ?
C3A N1A C1A C6A -61.6(9) . . . . ?
C4A C2A C5A Br1A -177.3(4) . . . . ?
C5A C2A C4A F1A 178.7(5) . . . . ?
C5A C2A C4A F2A -60.3(8) . . . . ?
C5A C2A C4A F3A 60.2(8) . . . . ?
C6A C1A N2A C2A -177.0(6) . . . . ?
C6A C7A C8A C9A 0.5(10) . . . . ?
C6A C7A C8A C12A 178.9(6) . . . . ?
C7A C6A C11A C10A -2.5(10) . . . . ?
C7A C8A C9A C10A 0.2(10) . . . . ?
C8A C9A C10A C11A -2.0(10) . . . . ?
C9A C10A C11A C6A 3.1(10) . . . . ?
C11A C6A C7A C8A 0.7(10) . . . . ?
C12A C8A C9A C10A -178.3(6) . . . . ?
O1B N1B C1B N2B 6.1(7) . . . . ?
O1B N1B C1B C6B 179.8(5) . . . . ?
O1B C2B C4B F1B 55.5(7) . . . . ?
O1B C2B C4B F2B 175.4(6) . . . . ?
O1B C2B C4B F3B -61.2(8) . . . . ?
O1B C2B C5B Br1B -63.1(6) . . . . ?
N1B O1B C2B N2B 6.0(7) . . . . ?
N1B O1B C2B C4B -111.4(5) . . . . ?
N1B O1B C2B C5B 130.9(5) . . . . ?
N1B C1B N2B C2B -2.4(8) . . . . ?
N1B C1B C6B C7B 165.3(6) . . . . ?
N1B C1B C6B C11B -19.3(9) . . . . ?
C1B N2B C2B O1B -2.5(7) . . . . ?
C1B N2B C2B C4B 114.1(6) . . . . ?
C1B N2B C2B C5B -125.6(6) . . . . ?
C1B C6B C7B C8B 177.1(5) . . . . ?
C1B C6B C11B C10B -178.6(6) . . . . ?
N2B C1B C6B C7B -21.4(9) . . . . ?
N2B C1B C6B C11B 154.0(6) . . . . ?
N2B C2B C4B F1B -61.3(7) . . . . ?
N2B C2B C4B F2B 58.5(8) . . . . ?
N2B C2B C4B F3B -178.0(6) . . . . ?
N2B C2B C5B Br1B 58.6(6) . . . . ?
C2B O1B N1B C1B -7.0(6) . . . . ?
C2B O1B N1B C3B -134.1(5) . . . . ?
C3B N1B C1B N2B 125.8(7) . . . . ?
C3B N1B C1B C6B -60.5(9) . . . . ?
C4B C2B C5B Br1B 179.4(4) . . . . ?
C5B C2B C4B F1B 174.9(5) . . . . ?
C5B C2B C4B F2B -65.2(7) . . . . ?
C5B C2B C4B F3B 58.3(8) . . . . ?
C6B C1B N2B C2B -175.9(6) . . . . ?
C6B C7B C8B C9B 0.6(9) . . . . ?
C6B C7B C8B C12B -179.3(6) . . . . ?
C7B C6B C11B C10B -3.2(9) . . . . ?
C7B C8B C9B C10B -1.2(9) . . . . ?
C8B C9B C10B C11B -0.4(10) . . . . ?
C9B C10B C11B C6B 2.6(9) . . . . ?
C11B C6B C7B C8B 1.6(9) . . . . ?
C12B C8B C9B C10B 178.7(6) . . . . ?

