# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2023

####################################################################### 
# 
# 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_exp_2157_Abs_twin1_hklf5
_database_code_depnum_ccdc_archive 'CCDC 2270167'
loop_
_audit_author_name
_audit_author_address
'Przemyslaw Malinowski'
;University of Warsaw
Poland
;
_audit_update_record             
;
2023-06-15 deposited with the CCDC.	2023-09-18 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT340_exp_2157_Abs_twin1_hklf5 
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.01052 Ang.  
RESPONSE: The problem is caused by disorder in the structure which is hard
to describe as it has low occupancy (as judged from weak q-peaks and would 
result in large rise of parameters refined.
;
# end Validation Reply Form 
_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H16 F3 N O2'
_chemical_formula_weight         371.35

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_H-M_alt        'I a'
_space_group_name_Hall           'I -2ya'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'x+1/2, -y, z'
'x+1/2, y+1/2, z+1/2'
'x+1, -y+1/2, z+1/2'

_cell_length_a                   8.0221(5)
_cell_length_b                   19.1612(8)
_cell_length_c                   22.4553(10)
_cell_angle_alpha                90
_cell_angle_beta                 91.728(5)
_cell_angle_gamma                90
_cell_volume                     3450.1(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    10422
_cell_measurement_theta_min      2.9550
_cell_measurement_theta_max      75.3820

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.430
_exptl_crystal_F_000             1536
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.372
_exptl_crystal_size_mid          0.261
_exptl_crystal_size_min          0.166
_exptl_absorpt_coefficient_mu    0.968
_shelx_estimated_absorpt_T_min   0.715
_shelx_estimated_absorpt_T_max   0.856
_exptl_absorpt_correction_T_min  0.770
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.55a (Rigaku Oxford Diffraction, 2019)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, Atlas'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11701
_diffrn_reflns_av_unetI/netI     0.0210
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         3.032
_diffrn_reflns_theta_max         75.761
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.886
_diffrn_reflns_point_group_measured_fraction_full 0.911
_reflns_number_total             11701
_reflns_number_gt                10617
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.795
_reflns_Friedel_fraction_max     0.787
_reflns_Friedel_fraction_full    0.822

_reflns_special_details          
;
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;

_computing_data_collection       'CrysAlisPro 1.171.40.55a (Rigaku OD, 2019)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.55a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.55a (Rigaku OD, 2019)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
 Refined as a 2-component twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   0.43(19)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         11701
_refine_ls_number_parameters     544
_refine_ls_number_restraints     362
_refine_ls_R_factor_all          0.0935
_refine_ls_R_factor_gt           0.0892
_refine_ls_wR_factor_ref         0.2682
_refine_ls_wR_factor_gt          0.2583
_refine_ls_goodness_of_fit_ref   1.231
_refine_ls_restrained_S_all      1.240
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N005 N 0.1094(8) 0.1681(3) 0.4571(2) 0.0280(11) Uani 1 1 d . . . . .
N007 N 0.6125(8) 0.3309(3) 0.5439(2) 0.0272(11) Uani 1 1 d . . . . .
C1 C 0.2236(10) 0.0711(3) 0.5956(2) 0.0301(14) Uani 1 1 d D U . . .
C008 C 0.0029(9) 0.1527(4) 0.4081(3) 0.0300(13) Uani 1 1 d . . . . .
O1 O 0.2527(8) 0.2630(3) 0.4962(2) 0.0406(13) Uani 1 1 d . . . . .
O2 O -0.0573(8) 0.0972(3) 0.3980(2) 0.0376(11) Uani 1 1 d . . . . .
C00C C 0.3020(10) 0.0130(3) 0.5724(3) 0.0322(14) Uani 1 1 d . . . . .
H00C H 0.345210 -0.022354 0.598173 0.039 Uiso 1 1 calc R U . . .
C00D C 0.5157(9) 0.3449(3) 0.5928(3) 0.0285(13) Uani 1 1 d . . . . .
C00E C 0.1531(10) 0.2387(3) 0.4602(3) 0.0319(14) Uani 1 1 d . . . . .
C00F C 0.7697(10) 0.4865(3) 0.4266(3) 0.0335(14) Uani 1 1 d . . . . .
H00F H 0.806283 0.521416 0.399934 0.040 Uiso 1 1 calc R U . . .
C00G C 0.2080(11) 0.0792(4) 0.6617(3) 0.0427(17) Uani 1 1 d D U . . .
F1A F 0.291(5) 0.0312(12) 0.6924(5) 0.100(10) Uani 0.51(4) 1 d D U P A 1
F2A F 0.062(2) 0.085(2) 0.6803(10) 0.094(10) Uani 0.51(4) 1 d D U P A 1
F3A F 0.292(3) 0.1382(9) 0.6789(6) 0.062(5) Uani 0.51(4) 1 d D U P A 1
F4A F 0.061(3) 0.1119(14) 0.6731(8) 0.064(6) Uani 0.49(4) 1 d D U P A 2
F5A F 0.325(2) 0.107(2) 0.6896(9) 0.095(9) Uani 0.49(4) 1 d D U P A 2
F6A F 0.170(6) 0.0174(9) 0.6860(9) 0.108(11) Uani 0.49(4) 1 d D U P A 2
C00H C 0.6845(9) 0.4284(3) 0.4049(3) 0.0307(14) Uani 1 1 d D U . . .
C00I C 0.3167(11) 0.0070(3) 0.5113(3) 0.0348(15) Uani 1 1 d . . . . .
H00I H 0.370018 -0.032799 0.495238 0.042 Uiso 1 1 calc R U . . .
C00J C 0.2544(10) 0.0583(3) 0.4733(3) 0.0309(14) Uani 1 1 d . . . . .
H00J H 0.266225 0.054325 0.431437 0.037 Uiso 1 1 calc R U . . .
C00M C 0.3948(11) 0.1943(4) 0.3568(3) 0.0385(15) Uani 1 1 d . . . . .
H00M H 0.391675 0.241649 0.369177 0.046 Uiso 1 1 calc R U . . .
C00N C 0.6599(9) 0.2614(3) 0.5406(3) 0.0302(13) Uani 1 1 d . . . . .
C00O C 0.1745(9) 0.1158(3) 0.4971(3) 0.0280(13) Uani 1 1 d . . . . .
C00P C 0.1592(10) 0.1235(3) 0.5578(3) 0.0299(13) Uani 1 1 d . . . . .
H00P H 0.106091 0.163475 0.573655 0.036 Uiso 1 1 calc R U . . .
C00Q C 0.7873(11) 0.3351(4) 0.6746(3) 0.0364(16) Uani 1 1 d . . . . .
C00R C 0.2686(11) 0.0966(4) 0.3062(3) 0.0363(15) Uani 1 1 d . . . . .
H00R H 0.177633 0.076486 0.284205 0.044 Uiso 1 1 calc R U . . .
C00S C 0.6325(11) 0.2911(4) 0.6872(3) 0.0385(16) Uani 1 1 d . . . . .
H00S H 0.567938 0.315982 0.718091 0.046 Uiso 1 1 calc R U . . .
C00T C 0.0493(10) 0.2760(4) 0.4123(3) 0.0345(14) Uani 1 1 d . . . . .
H00T H -0.053432 0.292390 0.432241 0.041 Uiso 1 1 calc R U . . .
C00U C 0.4094(12) 0.0568(4) 0.3193(3) 0.0402(17) Uani 1 1 d . . . . .
H00U H 0.414174 0.009882 0.305779 0.048 Uiso 1 1 calc R U . . .
C00V C 0.7498(9) 0.4420(3) 0.5266(3) 0.0295(13) Uani 1 1 d . . . . .
H00V H 0.770945 0.446428 0.568330 0.035 Uiso 1 1 calc R U . . .
C00W C 0.7934(11) 0.4052(4) 0.6935(3) 0.0369(15) Uani 1 1 d . . . . .
H00W H 0.704309 0.424041 0.715331 0.044 Uiso 1 1 calc R U . . .
C00X C 0.9280(11) 0.4465(4) 0.6804(3) 0.0359(15) Uani 1 1 d . . . . .
H00X H 0.931924 0.493546 0.693737 0.043 Uiso 1 1 calc R U . . .
C00Y C 0.2593(10) 0.1661(3) 0.3251(3) 0.0340(15) Uani 1 1 d . . . . .
C00Z C 0.5136(10) 0.2796(4) 0.6316(3) 0.0335(14) Uani 1 1 d . . . . .
H00Z H 0.397696 0.270438 0.644784 0.040 Uiso 1 1 calc R U . . .
C010 C 0.1520(13) 0.3363(4) 0.3199(4) 0.047(2) Uani 1 1 d . . . . .
H010 H 0.180078 0.377957 0.299604 0.056 Uiso 1 1 calc R U . . .
C011 C 0.5419(11) 0.0842(4) 0.3515(3) 0.0394(16) Uani 1 1 d . . . . .
H011 H 0.637174 0.056405 0.360821 0.047 Uiso 1 1 calc R U . . .
C012 C 0.6559(12) 0.1582(4) 0.6141(3) 0.0410(17) Uani 1 1 d . . . . .
H01A H 0.585408 0.116601 0.606336 0.049 Uiso 1 1 calc R U . . .
H01B H 0.761559 0.151467 0.593175 0.049 Uiso 1 1 calc R U . . .
C013 C 0.1369(12) 0.2791(5) 0.2879(3) 0.0432(18) Uani 1 1 d . . . . .
H013 H 0.149898 0.282549 0.246110 0.052 Uiso 1 1 calc R U . . .
C014 C 0.1285(12) 0.3413(4) 0.3861(3) 0.0402(16) Uani 1 1 d . . . . .
H01C H 0.057097 0.382106 0.394289 0.048 Uiso 1 1 calc R U . . .
H01D H 0.238342 0.349277 0.406214 0.048 Uiso 1 1 calc R U . . .
C015 C 0.6501(11) 0.4219(4) 0.3390(3) 0.0401(16) Uani 1 1 d D U . . .
F1B F 0.572(6) 0.3633(16) 0.3246(12) 0.083(10) Uani 0.45(6) 1 d D U P B 1
F2B F 0.786(3) 0.423(2) 0.3079(11) 0.067(8) Uani 0.45(6) 1 d D U P B 1
F3B F 0.553(4) 0.4715(19) 0.3186(9) 0.083(9) Uani 0.45(6) 1 d D U P B 1
F4B F 0.613(5) 0.4828(8) 0.3139(8) 0.095(9) Uani 0.55(6) 1 d D U P B 2
F5B F 0.533(2) 0.3790(13) 0.3245(9) 0.061(5) Uani 0.55(6) 1 d D U P B 2
F6B F 0.788(2) 0.402(2) 0.3112(8) 0.070(8) Uani 0.55(6) 1 d D U P B 2
C016 C 0.6663(9) 0.3836(3) 0.5035(3) 0.0264(12) Uani 1 1 d . . . . .
C017 C 0.6943(13) 0.1631(4) 0.6800(4) 0.049(2) Uani 1 1 d . . . . .
H017 H 0.727801 0.121512 0.700027 0.058 Uiso 1 1 calc R U . . .
C018 C 1.0577(11) 0.4199(4) 0.6479(3) 0.0389(16) Uani 1 1 d . . . . .
H018 H 1.148431 0.449005 0.637862 0.047 Uiso 1 1 calc R U . . .
C019 C 0.9186(11) 0.3089(4) 0.6441(3) 0.0375(15) Uani 1 1 d . . . . .
H019 H 0.917244 0.261379 0.632181 0.045 Uiso 1 1 calc R U . . .
C01A C 0.8015(10) 0.4937(4) 0.4877(3) 0.0333(14) Uani 1 1 d . . . . .
H01E H 0.858459 0.533768 0.502723 0.040 Uiso 1 1 calc R U . . .
C01B C 0.5350(11) 0.1539(4) 0.3705(3) 0.0411(16) Uani 1 1 d . . . . .
H01F H 0.626018 0.173540 0.392729 0.049 Uiso 1 1 calc R U . . .
C01C C -0.0080(10) 0.2180(4) 0.3696(3) 0.0358(15) Uani 1 1 d . . . . .
H01G H -0.126800 0.226223 0.356650 0.043 Uiso 1 1 calc R U . . .
C01D C 0.6850(13) 0.2212(4) 0.7125(3) 0.047(2) Uani 1 1 d . . . . .
H01H H 0.712802 0.218429 0.753883 0.056 Uiso 1 1 calc R U . . .
C01E C 0.6306(10) 0.3762(3) 0.4432(3) 0.0296(13) Uani 1 1 d . . . . .
H01I H 0.571196 0.336712 0.428238 0.036 Uiso 1 1 calc R U . . .
C01F C 0.5666(10) 0.2225(4) 0.5883(3) 0.0338(14) Uani 1 1 d . . . . .
H01J H 0.461537 0.204900 0.568451 0.041 Uiso 1 1 calc R U . . .
O3 O 0.7522(8) 0.2373(3) 0.5041(2) 0.0407(12) Uani 1 1 d . . . . .
O4 O 0.4527(7) 0.4007(3) 0.6031(2) 0.0366(11) Uani 1 1 d . . . . .
C01H C 1.0544(11) 0.3507(5) 0.6302(4) 0.0426(16) Uani 1 1 d . . . . .
H01K H 1.144049 0.331841 0.608756 0.051 Uiso 1 1 calc R U . . .
C01I C 0.1003(10) 0.2090(4) 0.3136(3) 0.0351(15) Uani 1 1 d . . . . .
H01L H 0.030863 0.183140 0.283182 0.042 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
N005 C00E 1.398(9) . ?
N005 C008 1.404(8) . ?
N005 C00O 1.433(8) . ?
N007 C00N 1.386(8) . ?
N007 C00D 1.390(9) . ?
N007 C016 1.433(7) . ?
C1 C00C 1.389(9) . ?
C1 C00P 1.404(8) . ?
C1 C00G 1.501(8) . ?
C008 O2 1.188(9) . ?
C008 C01C 1.522(8) . ?
O1 C00E 1.213(9) . ?
C00C C00I 1.386(9) . ?
C00D O4 1.207(9) . ?
C00D C00Z 1.525(8) . ?
C00E C00T 1.519(9) . ?
C00F C00H 1.388(10) . ?
C00F C01A 1.394(9) . ?
C00G F5A 1.238(17) . ?
C00G F2A 1.259(18) . ?
C00G F1A 1.319(13) . ?
C00G F6A 1.343(15) . ?
C00G F3A 1.364(14) . ?
C00G F4A 1.364(16) . ?
C00H C01E 1.397(8) . ?
C00H C015 1.502(8) . ?
C00I C00J 1.386(9) . ?
C00J C00O 1.390(9) . ?
C00M C00Y 1.390(11) . ?
C00M C01B 1.392(12) . ?
C00N O3 1.213(9) . ?
C00N C01F 1.521(9) . ?
C00O C00P 1.380(9) . ?
C00Q C019 1.369(12) . ?
C00Q C00W 1.409(10) . ?
C00Q C00S 1.534(12) . ?
C00R C00U 1.387(12) . ?
C00R C00Y 1.401(10) . ?
C00S C01D 1.510(10) . ?
C00S C00Z 1.563(10) . ?
C00T C014 1.530(10) . ?
C00T C01C 1.530(10) . ?
C00U C011 1.372(13) . ?
C00V C01A 1.393(8) . ?
C00V C016 1.396(9) . ?
C00W C00X 1.378(12) . ?
C00X C018 1.385(12) . ?
C00Y C01I 1.533(11) . ?
C00Z C01F 1.534(10) . ?
C010 C013 1.313(14) . ?
C010 C014 1.506(12) . ?
C011 C01B 1.403(12) . ?
C012 C017 1.505(12) . ?
C012 C01F 1.530(10) . ?
C013 C01I 1.495(10) . ?
C015 F5B 1.281(16) . ?
C015 F3B 1.305(17) . ?
C015 F2B 1.310(19) . ?
C015 F1B 1.321(18) . ?
C015 F4B 1.325(14) . ?
C015 F6B 1.342(16) . ?
C016 C01E 1.384(8) . ?
C017 C01D 1.335(13) . ?
C018 C01H 1.383(12) . ?
C019 C01H 1.395(13) . ?
C01C C01I 1.559(11) . ?

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
C00E N005 C008 112.8(5) . . ?
C00E N005 C00O 124.0(6) . . ?
C008 N005 C00O 123.1(5) . . ?
C00N N007 C00D 112.9(5) . . ?
C00N N007 C016 123.7(6) . . ?
C00D N007 C016 123.3(5) . . ?
C00C C1 C00P 120.6(5) . . ?
C00C C1 C00G 120.4(6) . . ?
C00P C1 C00G 119.0(6) . . ?
O2 C008 N005 124.9(6) . . ?
O2 C008 C01C 127.7(6) . . ?
N005 C008 C01C 107.3(6) . . ?
C00I C00C C1 119.5(6) . . ?
O4 C00D N007 124.7(6) . . ?
O4 C00D C00Z 127.3(6) . . ?
N007 C00D C00Z 108.0(6) . . ?
O1 C00E N005 124.3(6) . . ?
O1 C00E C00T 128.9(6) . . ?
N005 C00E C00T 106.8(6) . . ?
C00H C00F C01A 119.9(6) . . ?
F2A C00G F1A 110.7(17) . . ?
F5A C00G F6A 111.2(18) . . ?
F2A C00G F3A 106.4(17) . . ?
F1A C00G F3A 101.1(15) . . ?
F5A C00G F4A 110.5(18) . . ?
F6A C00G F4A 96.9(17) . . ?
F5A C00G C1 117.4(12) . . ?
F2A C00G C1 116.3(12) . . ?
F1A C00G C1 112.9(9) . . ?
F6A C00G C1 109.7(10) . . ?
F3A C00G C1 108.0(8) . . ?
F4A C00G C1 109.3(10) . . ?
C00F C00H C01E 121.1(6) . . ?
C00F C00H C015 119.2(6) . . ?
C01E C00H C015 119.8(6) . . ?
C00J C00I C00C 120.7(6) . . ?
C00I C00J C00O 119.2(6) . . ?
C00Y C00M C01B 120.7(7) . . ?
O3 C00N N007 125.2(6) . . ?
O3 C00N C01F 127.7(6) . . ?
N007 C00N C01F 107.0(6) . . ?
C00P C00O C00J 121.4(6) . . ?
C00P C00O N005 120.2(6) . . ?
C00J C00O N005 118.4(6) . . ?
C00O C00P C1 118.6(6) . . ?
C019 C00Q C00W 118.7(8) . . ?
C019 C00Q C00S 122.0(7) . . ?
C00W C00Q C00S 119.3(8) . . ?
C00U C00R C00Y 120.6(7) . . ?
C01D C00S C00Q 109.8(7) . . ?
C01D C00S C00Z 109.4(6) . . ?
C00Q C00S C00Z 114.2(5) . . ?
C00E C00T C014 115.6(7) . . ?
C00E C00T C01C 104.5(5) . . ?
C014 C00T C01C 118.2(6) . . ?
C011 C00U C00R 121.0(7) . . ?
C01A C00V C016 119.0(6) . . ?
C00X C00W C00Q 120.2(7) . . ?
C00W C00X C018 120.4(7) . . ?
C00M C00Y C00R 118.5(7) . . ?
C00M C00Y C01I 120.8(6) . . ?
C00R C00Y C01I 120.7(7) . . ?
C00D C00Z C01F 102.4(5) . . ?
C00D C00Z C00S 108.9(6) . . ?
C01F C00Z C00S 115.6(6) . . ?
C013 C010 C014 125.5(7) . . ?
C00U C011 C01B 119.2(8) . . ?
C017 C012 C01F 113.7(7) . . ?
C010 C013 C01I 123.7(7) . . ?
C010 C014 C00T 113.2(7) . . ?
F3B C015 F2B 107.7(18) . . ?
F3B C015 F1B 105(2) . . ?
F2B C015 F1B 106(2) . . ?
F5B C015 F4B 107.7(16) . . ?
F5B C015 F6B 107.7(15) . . ?
F4B C015 F6B 103.6(17) . . ?
F5B C015 C00H 114.4(12) . . ?
F3B C015 C00H 112.1(12) . . ?
F2B C015 C00H 113.1(15) . . ?
F1B C015 C00H 112.5(13) . . ?
F4B C015 C00H 112.2(9) . . ?
F6B C015 C00H 110.6(11) . . ?
C01E C016 C00V 122.0(6) . . ?
C01E C016 N007 119.3(6) . . ?
C00V C016 N007 118.7(5) . . ?
C01D C017 C012 125.2(6) . . ?
C01H C018 C00X 119.7(8) . . ?
C00Q C019 C01H 121.3(7) . . ?
C00V C01A C00F 119.9(6) . . ?
C00M C01B C011 120.1(8) . . ?
C008 C01C C00T 103.2(5) . . ?
C008 C01C C01I 110.1(6) . . ?
C00T C01C C01I 114.9(6) . . ?
C017 C01D C00S 123.5(6) . . ?
C016 C01E C00H 118.1(6) . . ?
C00N C01F C012 115.3(7) . . ?
C00N C01F C00Z 104.3(5) . . ?
C012 C01F C00Z 118.0(6) . . ?
C018 C01H C019 119.6(8) . . ?
C013 C01I C00Y 112.0(7) . . ?
C013 C01I C01C 109.4(6) . . ?
C00Y C01I C01C 113.9(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
C00E N005 C008 O2 -176.0(7) . . . . ?
C00O N005 C008 O2 7.9(12) . . . . ?
C00E N005 C008 C01C 8.2(9) . . . . ?
C00O N005 C008 C01C -167.9(6) . . . . ?
C00P C1 C00C C00I 0.1(12) . . . . ?
C00G C1 C00C C00I -179.3(7) . . . . ?
C00N N007 C00D O4 -175.8(7) . . . . ?
C016 N007 C00D O4 8.1(11) . . . . ?
C00N N007 C00D C00Z 7.5(8) . . . . ?
C016 N007 C00D C00Z -168.7(6) . . . . ?
C008 N005 C00E O1 -174.6(7) . . . . ?
C00O N005 C00E O1 1.4(11) . . . . ?
C008 N005 C00E C00T 7.1(8) . . . . ?
C00O N005 C00E C00T -176.9(6) . . . . ?
C00C C1 C00G F5A 87(2) . . . . ?
C00P C1 C00G F5A -92(2) . . . . ?
C00C C1 C00G F2A -122(2) . . . . ?
C00P C1 C00G F2A 58(2) . . . . ?
C00C C1 C00G F1A 7(2) . . . . ?
C00P C1 C00G F1A -172(2) . . . . ?
C00C C1 C00G F6A -41(2) . . . . ?
C00P C1 C00G F6A 140(2) . . . . ?
C00C C1 C00G F3A 118.4(14) . . . . ?
C00P C1 C00G F3A -61.0(15) . . . . ?
C00C C1 C00G F4A -146.0(15) . . . . ?
C00P C1 C00G F4A 34.6(17) . . . . ?
C01A C00F C00H C01E -0.5(12) . . . . ?
C01A C00F C00H C015 179.5(7) . . . . ?
C1 C00C C00I C00J 0.2(12) . . . . ?
C00C C00I C00J C00O -0.9(12) . . . . ?
C00D N007 C00N O3 -175.5(7) . . . . ?
C016 N007 C00N O3 0.7(11) . . . . ?
C00D N007 C00N C01F 7.8(8) . . . . ?
C016 N007 C00N C01F -176.1(6) . . . . ?
C00I C00J C00O C00P 1.4(11) . . . . ?
C00I C00J C00O N005 -179.4(7) . . . . ?
C00E N005 C00O C00P 55.8(10) . . . . ?
C008 N005 C00O C00P -128.6(7) . . . . ?
C00E N005 C00O C00J -123.4(8) . . . . ?
C008 N005 C00O C00J 52.2(10) . . . . ?
C00J C00O C00P C1 -1.2(11) . . . . ?
N005 C00O C00P C1 179.7(7) . . . . ?
C00C C1 C00P C00O 0.4(11) . . . . ?
C00G C1 C00P C00O 179.8(7) . . . . ?
C019 C00Q C00S C01D 48.8(9) . . . . ?
C00W C00Q C00S C01D -133.0(7) . . . . ?
C019 C00Q C00S C00Z -74.4(9) . . . . ?
C00W C00Q C00S C00Z 103.7(7) . . . . ?
O1 C00E C00T C014 31.0(11) . . . . ?
N005 C00E C00T C014 -150.8(7) . . . . ?
O1 C00E C00T C01C 162.7(8) . . . . ?
N005 C00E C00T C01C -19.1(7) . . . . ?
C00Y C00R C00U C011 0.7(10) . . . . ?
C019 C00Q C00W C00X 1.1(10) . . . . ?
C00S C00Q C00W C00X -177.1(6) . . . . ?
C00Q C00W C00X C018 0.8(10) . . . . ?
C01B C00M C00Y C00R -1.4(10) . . . . ?
C01B C00M C00Y C01I 175.8(7) . . . . ?
C00U C00R C00Y C00M 0.5(10) . . . . ?
C00U C00R C00Y C01I -176.7(6) . . . . ?
O4 C00D C00Z C01F 164.3(7) . . . . ?
N007 C00D C00Z C01F -19.1(7) . . . . ?
O4 C00D C00Z C00S -72.7(10) . . . . ?
N007 C00D C00Z C00S 103.9(7) . . . . ?
C01D C00S C00Z C00D -158.1(7) . . . . ?
C00Q C00S C00Z C00D -34.6(9) . . . . ?
C01D C00S C00Z C01F -43.4(9) . . . . ?
C00Q C00S C00Z C01F 80.0(8) . . . . ?
C00R C00U C011 C01B -1.0(11) . . . . ?
C014 C010 C013 C01I -2.6(16) . . . . ?
C013 C010 C014 C00T -11.9(14) . . . . ?
C00E C00T C014 C010 120.1(8) . . . . ?
C01C C00T C014 C010 -4.8(11) . . . . ?
C00F C00H C015 F5B -160.9(15) . . . . ?
C01E C00H C015 F5B 19.1(17) . . . . ?
C00F C00H C015 F3B -64(2) . . . . ?
C01E C00H C015 F3B 116(2) . . . . ?
C00F C00H C015 F2B 58(2) . . . . ?
C01E C00H C015 F2B -122(2) . . . . ?
C00F C00H C015 F1B 178(3) . . . . ?
C01E C00H C015 F1B -2(3) . . . . ?
C00F C00H C015 F4B -38(2) . . . . ?
C01E C00H C015 F4B 142(2) . . . . ?
C00F C00H C015 F6B 77.3(19) . . . . ?
C01E C00H C015 F6B -102.7(19) . . . . ?
C01A C00V C016 C01E -1.2(11) . . . . ?
C01A C00V C016 N007 -179.6(7) . . . . ?
C00N N007 C016 C01E 58.9(9) . . . . ?
C00D N007 C016 C01E -125.3(7) . . . . ?
C00N N007 C016 C00V -122.6(7) . . . . ?
C00D N007 C016 C00V 53.2(10) . . . . ?
C01F C012 C017 C01D -12.9(14) . . . . ?
C00W C00X C018 C01H -2.1(10) . . . . ?
C00W C00Q C019 C01H -1.8(10) . . . . ?
C00S C00Q C019 C01H 176.4(6) . . . . ?
C016 C00V C01A C00F 0.0(12) . . . . ?
C00H C00F C01A C00V 0.9(12) . . . . ?
C00Y C00M C01B C011 1.1(11) . . . . ?
C00U C011 C01B C00M 0.1(11) . . . . ?
O2 C008 C01C C00T 164.8(8) . . . . ?
N005 C008 C01C C00T -19.5(8) . . . . ?
O2 C008 C01C C01I -72.0(10) . . . . ?
N005 C008 C01C C01I 103.7(7) . . . . ?
C00E C00T C01C C008 23.0(7) . . . . ?
C014 C00T C01C C008 153.2(7) . . . . ?
C00E C00T C01C C01I -96.9(7) . . . . ?
C014 C00T C01C C01I 33.3(9) . . . . ?
C012 C017 C01D C00S 0.4(17) . . . . ?
C00Q C00S C01D C017 -98.2(11) . . . . ?
C00Z C00S C01D C017 27.8(13) . . . . ?
C00V C016 C01E C00H 1.6(10) . . . . ?
N007 C016 C01E C00H 180.0(7) . . . . ?
C00F C00H C01E C016 -0.7(11) . . . . ?
C015 C00H C01E C016 179.3(7) . . . . ?
O3 C00N C01F C012 32.7(10) . . . . ?
N007 C00N C01F C012 -150.6(6) . . . . ?
O3 C00N C01F C00Z 163.8(7) . . . . ?
N007 C00N C01F C00Z -19.5(7) . . . . ?
C017 C012 C01F C00N 118.9(8) . . . . ?
C017 C012 C01F C00Z -5.3(11) . . . . ?
C00D C00Z C01F C00N 22.7(7) . . . . ?
C00S C00Z C01F C00N -95.6(7) . . . . ?
C00D C00Z C01F C012 152.2(7) . . . . ?
C00S C00Z C01F C012 34.0(9) . . . . ?
C00X C018 C01H C019 1.4(11) . . . . ?
C00Q C019 C01H C018 0.5(11) . . . . ?
C010 C013 C01I C00Y -96.3(11) . . . . ?
C010 C013 C01I C01C 31.0(12) . . . . ?
C00M C00Y C01I C013 50.8(9) . . . . ?
C00R C00Y C01I C013 -132.0(7) . . . . ?
C00M C00Y C01I C01C -74.0(8) . . . . ?
C00R C00Y C01I C01C 103.1(7) . . . . ?
C008 C01C C01I C013 -160.6(6) . . . . ?
C00T C01C C01I C013 -44.5(8) . . . . ?
C008 C01C C01I C00Y -34.3(8) . . . . ?
C00T C01C C01I C00Y 81.7(7) . . . . ?

_refine_diff_density_max         0.448
_refine_diff_density_min         -0.357
_refine_diff_density_rms         0.072

####################################################################### 
# 
# 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_exp_2150_a
_database_code_depnum_ccdc_archive 'CCDC 2270168'
loop_
_audit_author_name
_audit_author_address
'Przemyslaw Malinowski'
;University of Warsaw
Poland
;
_audit_update_record             
;
2023-06-15 deposited with the CCDC.	2023-09-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C11 H6 F3 N O2'
_chemical_formula_weight         241.17

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, 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                   10.6040(2)
_cell_length_b                   11.7299(2)
_cell_length_c                   15.5267(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1931.27(6)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    14230
_cell_measurement_theta_min      4.1110
_cell_measurement_theta_max      75.5040

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.659
_exptl_crystal_F_000             976
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.160
_exptl_absorpt_coefficient_mu    1.354
_shelx_estimated_absorpt_T_min   0.764
_shelx_estimated_absorpt_T_max   0.813
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_correction_T_min  0.545
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   
'CrysAlisPro 1.171.41.112a (Rigaku Oxford Diffraction, 2021) Numerical absorption correction based on gaussian integration over a multifaceted crystal model Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, Atlas'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            21232
_diffrn_reflns_av_unetI/netI     0.0113
_diffrn_reflns_av_R_equivalents  0.0297
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         5.699
_diffrn_reflns_theta_max         75.751
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2006
_reflns_number_gt                1886
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrysAlisPro 1.171.41.112a (Rigaku OD, 2021)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.112a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.112a (Rigaku OD, 2021)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0363P)²+1.0286P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2006
_refine_ls_number_parameters     154
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0332
_refine_ls_R_factor_gt           0.0313
_refine_ls_wR_factor_ref         0.0801
_refine_ls_wR_factor_gt          0.0784
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_restrained_S_all      1.069
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F001 F 0.23163(8) 0.43170(8) 0.63978(5) 0.0354(2) Uani 1 1 d . . . . .
F002 F 0.07314(8) 0.43468(9) 0.55506(6) 0.0406(2) Uani 1 1 d . . . . .
F003 F 0.18693(10) 0.28467(7) 0.56465(6) 0.0410(2) Uani 1 1 d . . . . .
O004 O 0.49276(8) 0.79007(7) 0.37999(6) 0.0208(2) Uani 1 1 d . . . . .
O005 O 0.10965(8) 0.65418(7) 0.29157(5) 0.0201(2) Uani 1 1 d . . . . .
N006 N 0.30707(9) 0.69315(8) 0.34887(6) 0.0159(2) Uani 1 1 d . . . . .
C007 C 0.20026(11) 0.71590(9) 0.29843(7) 0.0162(2) Uani 1 1 d . . . . .
C008 C 0.24859(11) 0.54590(9) 0.45239(7) 0.0162(2) Uani 1 1 d . . . . .
H008 H 0.175144 0.587719 0.467544 0.019 Uiso 1 1 calc R U . . .
C009 C 0.33204(11) 0.58734(9) 0.39093(7) 0.0156(2) Uani 1 1 d . . . . .
C00A C 0.33316(12) 0.86963(10) 0.28483(7) 0.0183(2) Uani 1 1 d . . . . .
H00A H 0.368600 0.941141 0.269371 0.022 Uiso 1 1 calc R U . . .
C00B C 0.43994(11) 0.52702(10) 0.36849(7) 0.0172(2) Uani 1 1 d . . . . .
H00B H 0.496287 0.556596 0.326500 0.021 Uiso 1 1 calc R U . . .
C00C C 0.27514(11) 0.44149(10) 0.49131(7) 0.0169(2) Uani 1 1 d . . . . .
C00D C 0.39270(11) 0.78421(9) 0.34333(7) 0.0165(2) Uani 1 1 d . . . . .
C00E C 0.38286(11) 0.37976(9) 0.46976(8) 0.0181(2) Uani 1 1 d . . . . .
H00E H 0.400116 0.308928 0.496984 0.022 Uiso 1 1 calc R U . . .
C00F C 0.46478(11) 0.42297(10) 0.40801(8) 0.0185(2) Uani 1 1 d . . . . .
H00F H 0.538193 0.381208 0.392684 0.022 Uiso 1 1 calc R U . . .
C00G C 0.22287(11) 0.82987(9) 0.25784(8) 0.0184(2) Uani 1 1 d . . . . .
H00G H 0.167384 0.867521 0.219128 0.022 Uiso 1 1 calc R U . . .
C00H C 0.19104(12) 0.39849(10) 0.56184(8) 0.0203(3) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F001 C00H 1.3422(14) . ?
F002 C00H 1.3245(15) . ?
F003 C00H 1.3366(14) . ?
O004 C00D 1.2060(15) . ?
O005 C007 1.2078(15) . ?
N006 C007 1.4026(15) . ?
N006 C00D 1.4046(14) . ?
N006 C009 1.4272(14) . ?
C007 C00G 1.4972(15) . ?
C008 C009 1.3892(16) . ?
C008 C00C 1.3945(15) . ?
C009 C00B 1.3897(16) . ?
C00A C00G 1.3270(18) . ?
C00A C00D 1.4925(16) . ?
C00B C00F 1.3912(16) . ?
C00C C00E 1.3932(17) . ?
C00C C00H 1.4996(16) . ?
C00E C00F 1.3895(17) . ?

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
C007 N006 C00D 110.07(9) . . ?
C007 N006 C009 124.80(9) . . ?
C00D N006 C009 124.71(10) . . ?
O005 C007 N006 125.28(10) . . ?
O005 C007 C00G 128.72(11) . . ?
N006 C007 C00G 106.00(10) . . ?
C009 C008 C00C 118.45(11) . . ?
C008 C009 C00B 121.23(10) . . ?
C008 C009 N006 120.03(10) . . ?
C00B C009 N006 118.74(10) . . ?
C00G C00A C00D 109.22(10) . . ?
C009 C00B C00F 119.48(11) . . ?
C00E C00C C008 121.19(11) . . ?
C00E C00C C00H 119.22(10) . . ?
C008 C00C C00H 119.46(11) . . ?
O004 C00D N006 125.67(11) . . ?
O004 C00D C00A 128.40(11) . . ?
N006 C00D C00A 105.92(10) . . ?
C00F C00E C00C 119.26(10) . . ?
C00E C00F C00B 120.39(11) . . ?
C00A C00G C007 108.78(10) . . ?
F002 C00H F003 106.97(11) . . ?
F002 C00H F001 106.34(11) . . ?
F003 C00H F001 105.72(10) . . ?
F002 C00H C00C 113.30(10) . . ?
F003 C00H C00C 112.28(10) . . ?
F001 C00H C00C 111.72(10) . . ?

_refine_diff_density_max         0.292
_refine_diff_density_min         -0.269
_refine_diff_density_rms         0.044

####################################################################### 
# 
# 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_exp_2145_a
_database_code_depnum_ccdc_archive 'CCDC 2270169'
loop_
_audit_author_name
_audit_author_address
'Przemyslaw Malinowski'
;University of Warsaw
Poland
;
_audit_update_record             
;
2023-06-15 deposited with the CCDC.	2023-09-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H16 F N O2'
_chemical_formula_weight         321.34

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   5.94460(10)
_cell_length_b                   24.1479(4)
_cell_length_c                   10.6246(2)
_cell_angle_alpha                90
_cell_angle_beta                 100.951(2)
_cell_angle_gamma                90
_cell_volume                     1497.38(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    103(2)
_cell_measurement_reflns_used    19715
_cell_measurement_theta_min      3.5890
_cell_measurement_theta_max      76.0380

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.425
_exptl_crystal_F_000             672
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.390
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    0.825
_shelx_estimated_absorpt_T_min   0.739
_shelx_estimated_absorpt_T_max   0.937
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_correction_T_min  0.457
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   
'CrysAlisPro 1.171.41.112a (Rigaku Oxford Diffraction, 2021) Numerical absorption correction based on gaussian integration over a multifaceted crystal model Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      103(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, Atlas'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            33471
_diffrn_reflns_av_unetI/netI     0.0200
_diffrn_reflns_av_R_equivalents  0.0559
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         3.661
_diffrn_reflns_theta_max         78.052
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3125
_reflns_number_gt                2909
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrysAlisPro 1.171.41.112a (Rigaku OD, 2021)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.112a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.112a (Rigaku OD, 2021)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0561P)²+0.6612P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3125
_refine_ls_number_parameters     217
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0430
_refine_ls_R_factor_gt           0.0405
_refine_ls_wR_factor_ref         0.1097
_refine_ls_wR_factor_gt          0.1057
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_restrained_S_all      1.059
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F001 F 0.43397(14) 0.68809(4) 0.85076(7) 0.0287(2) Uani 1 1 d . . . . .
O002 O -0.00077(16) 0.71346(4) 0.27076(9) 0.0253(2) Uani 1 1 d . . . . .
O003 O 0.67324(15) 0.61797(4) 0.31904(9) 0.0233(2) Uani 1 1 d . . . . .
N004 N 0.34354(18) 0.66724(4) 0.32629(10) 0.0177(2) Uani 1 1 d . . . . .
C005 C 0.1601(2) 0.69013(5) 0.24006(12) 0.0188(3) Uani 1 1 d . . . . .
C006 C 0.5697(2) 0.69317(5) 0.53366(12) 0.0191(3) Uani 1 1 d . . . . .
H006 H 0.690722 0.704251 0.492315 0.023 Uiso 1 1 calc R U . . .
C007 C 0.1887(2) 0.65527(5) 0.52098(12) 0.0189(3) Uani 1 1 d . . . . .
H007 H 0.052329 0.640470 0.471063 0.023 Uiso 1 1 calc R U . . .
C008 C 0.4981(2) 0.63909(5) 0.26445(12) 0.0184(3) Uani 1 1 d . . . . .
C009 C 0.3681(2) 0.67170(5) 0.46252(11) 0.0174(3) Uani 1 1 d . . . . .
C00A C 0.4122(2) 0.68203(5) 0.72163(12) 0.0207(3) Uani 1 1 d . . . . .
C00B C 0.5928(2) 0.69830(5) 0.66598(12) 0.0208(3) Uani 1 1 d . . . . .
H00B H 0.729374 0.712645 0.716553 0.025 Uiso 1 1 calc R U . . .
C00C C 0.2101(2) 0.66064(5) 0.65301(12) 0.0204(3) Uani 1 1 d . . . . .
H00C H 0.089279 0.649913 0.694857 0.024 Uiso 1 1 calc R U . . .
C00D C 0.0968(2) 0.54400(5) 0.24223(12) 0.0221(3) Uani 1 1 d . . . . .
H00D H -0.015810 0.571493 0.214076 0.026 Uiso 1 1 calc R U . . .
C00E C 0.2867(2) 0.53960(5) 0.18387(12) 0.0215(3) Uani 1 1 d . . . . .
C00F C 0.3986(2) 0.63866(5) 0.12144(12) 0.0203(3) Uani 1 1 d . . . . .
H00F H 0.520187 0.650838 0.074111 0.024 Uiso 1 1 calc R U . . .
C00G C 0.2113(2) 0.68345(5) 0.10640(12) 0.0199(3) Uani 1 1 d . . . . .
H00G H 0.287461 0.718654 0.087886 0.024 Uiso 1 1 calc R U . . .
C00H C 0.3190(2) 0.57857(6) 0.07561(12) 0.0235(3) Uani 1 1 d . . . . .
H00H H 0.443566 0.562389 0.035681 0.028 Uiso 1 1 calc R U . . .
C00I C -0.0017(2) 0.67775(6) 0.00014(13) 0.0258(3) Uani 1 1 d . . . . .
H00A H -0.138576 0.687851 0.035622 0.031 Uiso 1 1 calc R U . . .
H00E H 0.010431 0.704461 -0.068950 0.031 Uiso 1 1 calc R U . . .
C00J C 0.4494(2) 0.49868(6) 0.22602(14) 0.0283(3) Uani 1 1 d . . . . .
H00J H 0.578943 0.494831 0.186363 0.034 Uiso 1 1 calc R U . . .
C00K C 0.1053(3) 0.57886(6) -0.02634(13) 0.0292(3) Uani 1 1 d . . . . .
H00K H 0.068469 0.545553 -0.073336 0.035 Uiso 1 1 calc R U . . .
C00L C -0.0359(3) 0.62112(6) -0.05661(13) 0.0278(3) Uani 1 1 d . . . . .
H00L H -0.169978 0.614954 -0.119581 0.033 Uiso 1 1 calc R U . . .
C00M C 0.0706(3) 0.50844(6) 0.34149(13) 0.0292(3) Uani 1 1 d . . . . .
H00M H -0.059580 0.511786 0.380809 0.035 Uiso 1 1 calc R U . . .
C00N C 0.4229(3) 0.46360(6) 0.32549(15) 0.0343(4) Uani 1 1 d . . . . .
H00N H 0.535634 0.436202 0.354215 0.041 Uiso 1 1 calc R U . . .
C00O C 0.2343(3) 0.46806(6) 0.38323(14) 0.0342(4) Uani 1 1 d . . . . .
H00O H 0.216632 0.443727 0.450937 0.041 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
F001 C00A 1.3612(14) . ?
O002 C005 1.2072(16) . ?
O003 C008 1.2046(16) . ?
N004 C005 1.3979(16) . ?
N004 C008 1.4025(16) . ?
N004 C009 1.4309(15) . ?
C005 C00G 1.5164(17) . ?
C006 C009 1.3900(17) . ?
C006 C00B 1.3918(17) . ?
C007 C009 1.3902(18) . ?
C007 C00C 1.3903(17) . ?
C008 C00F 1.5222(16) . ?
C00A C00B 1.3773(19) . ?
C00A C00C 1.3814(18) . ?
C00D C00E 1.3913(18) . ?
C00D C00M 1.3915(19) . ?
C00E C00J 1.3957(19) . ?
C00E C00H 1.5262(18) . ?
C00F C00G 1.5384(18) . ?
C00F C00H 1.5744(18) . ?
C00G C00I 1.5344(17) . ?
C00H C00K 1.505(2) . ?
C00I C00L 1.493(2) . ?
C00J C00N 1.387(2) . ?
C00K C00L 1.322(2) . ?
C00M C00O 1.390(2) . ?
C00N C00O 1.380(2) . ?

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
C005 N004 C008 112.54(10) . . ?
C005 N004 C009 123.38(10) . . ?
C008 N004 C009 124.08(10) . . ?
O002 C005 N004 124.53(11) . . ?
O002 C005 C00G 127.80(11) . . ?
N004 C005 C00G 107.54(10) . . ?
C009 C006 C00B 119.46(12) . . ?
C009 C007 C00C 119.53(11) . . ?
O003 C008 N004 124.25(11) . . ?
O003 C008 C00F 127.89(11) . . ?
N004 C008 C00F 107.82(10) . . ?
C006 C009 C007 121.25(11) . . ?
C006 C009 N004 119.34(11) . . ?
C007 C009 N004 119.40(11) . . ?
F001 C00A C00B 118.00(11) . . ?
F001 C00A C00C 118.60(12) . . ?
C00B C00A C00C 123.39(12) . . ?
C00A C00B C006 118.22(12) . . ?
C00A C00C C007 118.13(12) . . ?
C00E C00D C00M 120.53(13) . . ?
C00D C00E C00J 118.84(13) . . ?
C00D C00E C00H 121.18(12) . . ?
C00J C00E C00H 119.98(12) . . ?
C008 C00F C00G 103.60(10) . . ?
C008 C00F C00H 110.61(10) . . ?
C00G C00F C00H 116.55(11) . . ?
C005 C00G C00I 114.47(11) . . ?
C005 C00G C00F 104.33(10) . . ?
C00I C00G C00F 119.55(11) . . ?
C00K C00H C00E 109.60(11) . . ?
C00K C00H C00F 112.41(11) . . ?
C00E C00H C00F 114.11(10) . . ?
C00L C00I C00G 114.16(12) . . ?
C00N C00J C00E 120.32(14) . . ?
C00L C00K C00H 126.09(13) . . ?
C00K C00L C00I 125.28(13) . . ?
C00O C00M C00D 120.15(14) . . ?
C00O C00N C00J 120.70(14) . . ?
C00N C00O C00M 119.45(14) . . ?

_refine_diff_density_max         0.279
_refine_diff_density_min         -0.224
_refine_diff_density_rms         0.048

