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

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

data_iv6
_audit_block_doi                 10.5517/ccdc.csd.cc2gfz2z
_database_code_depnum_ccdc_archive 'CCDC 2277541'
loop_
_citation_id
_citation_doi
_citation_year
1 10.26434/chemrxiv-2023-qk7sx 2023
loop_
_audit_author_name
_audit_author_address
'E. Rusanov'
;ETH Zurich
Switzerland
;
_audit_update_record             
;
2023-06-28 deposited with the CCDC.	2024-02-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/4
_shelx_SHELXL_version_number     2016/4
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C8 H6 F3 N O2'
_chemical_formula_sum            'C8 H6 F3 N O2'
_chemical_formula_weight         205.14

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

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

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

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

_cell_length_a                   14.9715(7)
_cell_length_b                   7.8801(4)
_cell_length_c                   15.8936(8)
_cell_angle_alpha                90
_cell_angle_beta                 116.348(2)
_cell_angle_gamma                90
_cell_volume                     1680.28(15)
_cell_formula_units_Z            8
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    1064
_cell_measurement_theta_min      2.86
_cell_measurement_theta_max      21.42
_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.622
_exptl_crystal_F_000             832
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.380
_exptl_crystal_size_mid          0.320
_exptl_crystal_size_min          0.070
_exptl_absorpt_coefficient_mu    0.159
_shelx_estimated_absorpt_T_min   0.942
_shelx_estimated_absorpt_T_max   0.989
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6749
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5085
_diffrn_reflns_av_unetI/netI     0.0571
_diffrn_reflns_av_R_equivalents  0.0399
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.860
_diffrn_reflns_theta_max         26.726
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             1745
_reflns_number_gt                1125
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2016/4 (Sheldrick, 2016)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0500P)²+0.2479P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1745
_refine_ls_number_parameters     151
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0851
_refine_ls_R_factor_gt           0.0490
_refine_ls_wR_factor_ref         0.1165
_refine_ls_wR_factor_gt          0.1019
_refine_ls_goodness_of_fit_ref   1.008
_refine_ls_restrained_S_all      1.008
_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
C1 C 0.12668(17) 0.6690(3) -0.20260(16) 0.0330(6) Uani 1 1 d . . . . .
C2 C 0.11806(18) 0.7591(3) -0.13314(15) 0.0312(6) Uani 1 1 d . . . . .
C3 C 0.13119(16) 0.6828(3) -0.04890(15) 0.0269(5) Uani 1 1 d . . . . .
C4 C 0.15780(19) 0.5090(3) -0.03830(16) 0.0334(6) Uani 1 1 d . . . . .
C5 C 0.1648(2) 0.4246(3) -0.11090(16) 0.0376(6) Uani 1 1 d . . . . .
C6 C 0.11858(17) 0.7888(3) 0.01996(15) 0.0281(5) Uani 1 1 d . . . . .
C7 C 0.12073(17) 0.7458(3) 0.10283(15) 0.0301(5) Uani 1 1 d . . . . .
C8 C 0.10143(19) 0.8828(3) 0.15949(16) 0.0371(6) Uani 1 1 d . . . . .
F1 F 0.10147(13) 1.04089(16) 0.12939(10) 0.0529(5) Uani 1 1 d . . . . .
F2 F 0.01301(12) 0.8615(2) 0.16012(12) 0.0635(5) Uani 1 1 d . . . . .
F3 F 0.16918(12) 0.87963(18) 0.24969(10) 0.0556(5) Uani 1 1 d . . . . .
N1 N 0.14851(15) 0.5041(3) -0.19086(14) 0.0345(5) Uani 1 1 d . . . . .
O1 O 0.18035(18) 0.4189(2) 0.03978(13) 0.0609(7) Uani 1 1 d . . . . .
O2 O 0.13570(15) 0.6001(2) 0.14379(11) 0.0485(5) Uani 1 1 d . . . . .
H2 H 0.1048(16) 0.887(3) -0.1413(14) 0.031(6) Uiso 1 1 d . . . . .
H1 H 0.1169(18) 0.726(3) -0.2596(17) 0.047(7) Uiso 1 1 d . . . . .
H5 H 0.1813(19) 0.305(3) -0.1058(17) 0.052(8) Uiso 1 1 d . . . . .
H1N H 0.149(2) 0.451(4) -0.242(2) 0.071(9) Uiso 1 1 d . . . . .
H6 H 0.1053(16) 0.903(3) 0.0008(16) 0.033(6) Uiso 1 1 d . . . . .
H1O H 0.159(3) 0.478(4) 0.076(3) 0.112(14) Uiso 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.333(3) . ?
C1 C2 1.366(3) . ?
C2 C3 1.400(3) . ?
C3 C4 1.415(3) . ?
C3 C6 1.454(3) . ?
C4 O1 1.336(3) . ?
C4 C5 1.376(3) . ?
C5 N1 1.338(3) . ?
C6 C7 1.346(3) . ?
C7 O2 1.290(3) . ?
C7 C8 1.513(3) . ?
C8 F1 1.335(3) . ?
C8 F2 1.339(3) . ?
C8 F3 1.339(3) . ?

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
N1 C1 C2 119.9(2) . . ?
C1 C2 C3 121.8(2) . . ?
C2 C3 C4 116.24(19) . . ?
C2 C3 C6 117.6(2) . . ?
C4 C3 C6 126.15(19) . . ?
O1 C4 C5 116.1(2) . . ?
O1 C4 C3 124.49(19) . . ?
C5 C4 C3 119.4(2) . . ?
N1 C5 C4 121.4(2) . . ?
C7 C6 C3 129.6(2) . . ?
O2 C7 C6 129.9(2) . . ?
O2 C7 C8 111.78(18) . . ?
C6 C7 C8 118.3(2) . . ?
F1 C8 F2 106.10(19) . . ?
F1 C8 F3 106.3(2) . . ?
F2 C8 F3 105.74(18) . . ?
F1 C8 C7 114.95(18) . . ?
F2 C8 C7 111.5(2) . . ?
F3 C8 C7 111.7(2) . . ?
C1 N1 C5 121.3(2) . . ?

_refine_diff_density_max         0.222
_refine_diff_density_min         -0.206
_refine_diff_density_rms         0.049



####################################################################### 
# 
# 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_iv7
_audit_block_doi                 10.5517/ccdc.csd.cc2gfz30
_database_code_depnum_ccdc_archive 'CCDC 2277542'
loop_
_citation_id
_citation_doi
_citation_year
1 10.26434/chemrxiv-2023-qk7sx 2023
loop_
_audit_author_name
_audit_author_address
'E. Rusanov'
;ETH Zurich
Switzerland
;
_audit_update_record             
;
2023-06-28 deposited with the CCDC.	2024-02-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/4
_shelx_SHELXL_version_number     2016/4
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C11 H6 F6 N2 O'
_chemical_formula_sum            'C11 H6 F6 N2 O'
_chemical_formula_weight         296.18

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

_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'

_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'

_cell_length_a                   4.6838(3)
_cell_length_b                   15.0703(8)
_cell_length_c                   15.9130(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1123.24(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    2022
_cell_measurement_theta_min      2.56
_cell_measurement_theta_max      20.98
_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.751
_exptl_crystal_F_000             592
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.540
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.182
_shelx_estimated_absorpt_T_min   0.908
_shelx_estimated_absorpt_T_max   0.982
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6536
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6354
_diffrn_reflns_av_unetI/netI     0.0623
_diffrn_reflns_av_R_equivalents  0.0440
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.560
_diffrn_reflns_theta_max         26.422
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2291
_reflns_number_gt                1737
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.673
_reflns_Friedel_fraction_max     0.996
_reflns_Friedel_fraction_full    0.999

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2016/4 (Sheldrick, 2016)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0262P)²+0.2533P] 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 
;
 Flack x determined using 536 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.6(8)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2291
_refine_ls_number_parameters     182
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0692
_refine_ls_R_factor_gt           0.0476
_refine_ls_wR_factor_ref         0.0923
_refine_ls_wR_factor_gt          0.0843
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_restrained_S_all      1.015
_refine_ls_shift/su_max          0.008
_refine_ls_shift/su_mean         0.001

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.2465(9) -0.0082(3) 1.1006(2) 0.0360(10) Uani 1 1 d . . . . .
H1 H 0.158040 -0.045989 1.140666 0.043 Uiso 1 1 calc R U . . .
C2 C 0.4218(9) -0.0446(3) 1.0417(2) 0.0348(10) Uani 1 1 d . . . . .
H2 H 0.455436 -0.106748 1.040772 0.042 Uiso 1 1 calc R U . . .
C3 C 0.5525(9) 0.0113(2) 0.9820(2) 0.0281(9) Uani 1 1 d . . . . .
C4 C 0.4995(8) 0.1036(2) 0.9907(2) 0.0270(8) Uani 1 1 d . . . . .
C5 C 0.3187(8) 0.1371(2) 1.0505(2) 0.0301(9) Uani 1 1 d . . . . .
H5 H 0.282617 0.198982 1.053960 0.036 Uiso 1 1 calc R U . . .
C6 C 0.7356(8) 0.0037(2) 0.9101(2) 0.0272(8) Uani 1 1 d . . . . .
C7 C 0.7729(8) 0.0934(3) 0.8836(2) 0.0284(9) Uani 1 1 d . . . . .
C8 C -0.0026(10) 0.1143(3) 1.1698(2) 0.0422(11) Uani 1 1 d . . . . .
H8A H 0.091503 0.111279 1.224693 0.063 Uiso 1 1 calc R U . . .
H8B H -0.176121 0.077967 1.170715 0.063 Uiso 1 1 calc R U . . .
H8C H -0.052970 0.175994 1.157244 0.063 Uiso 1 1 calc R U . . .
C9 C 0.8489(9) -0.0731(3) 0.8675(2) 0.0317(9) Uani 1 1 d . . . . .
C10 C 0.7806(9) -0.1658(3) 0.9033(3) 0.0419(10) Uani 1 1 d . . . . .
C11 C 0.9305(9) 0.1266(3) 0.8077(3) 0.0369(10) Uani 1 1 d . . . . .
F1 F 0.9031(7) -0.22937(16) 0.85872(16) 0.0659(9) Uani 1 1 d . . . . .
F2 F 0.8693(6) -0.17487(15) 0.98270(14) 0.0503(7) Uani 1 1 d . . . . .
F3 F 0.4972(6) -0.18083(15) 0.90271(16) 0.0532(7) Uani 1 1 d . . . . .
F4 F 0.8023(5) 0.10163(16) 0.73598(12) 0.0439(6) Uani 1 1 d . . . . .
F5 F 1.1995(5) 0.09793(18) 0.80244(14) 0.0544(7) Uani 1 1 d . . . . .
F6 F 0.9415(7) 0.21445(15) 0.80635(16) 0.0658(9) Uani 1 1 d . . . . .
N1 N 0.1939(7) 0.0804(2) 1.10412(17) 0.0318(8) Uani 1 1 d . . . . .
N2 N 0.6381(7) 0.15307(19) 0.92991(17) 0.0299(8) Uani 1 1 d . . . . .
O1 O 0.9882(6) -0.07161(17) 0.80345(17) 0.0452(7) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.358(5) . ?
C1 C2 1.362(5) . ?
C2 C3 1.408(5) . ?
C3 C4 1.420(5) . ?
C3 C6 1.435(5) . ?
C4 C5 1.370(5) . ?
C4 N2 1.383(4) . ?
C5 N1 1.341(5) . ?
C6 C7 1.427(5) . ?
C6 C9 1.443(5) . ?
C7 N2 1.324(4) . ?
C7 C11 1.501(5) . ?
C8 N1 1.483(5) . ?
C9 O1 1.210(4) . ?
C9 C10 1.542(6) . ?
C10 F1 1.322(4) . ?
C10 F2 1.338(5) . ?
C10 F3 1.346(5) . ?
C11 F6 1.325(4) . ?
C11 F5 1.335(5) . ?
C11 F4 1.344(4) . ?

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
N1 C1 C2 122.2(3) . . ?
C1 C2 C3 119.0(4) . . ?
C2 C3 C4 116.4(3) . . ?
C2 C3 C6 138.5(3) . . ?
C4 C3 C6 105.1(3) . . ?
C5 C4 N2 125.3(3) . . ?
C5 C4 C3 122.4(3) . . ?
N2 C4 C3 112.2(3) . . ?
N1 C5 C4 118.5(4) . . ?
C7 C6 C3 103.5(3) . . ?
C7 C6 C9 125.1(3) . . ?
C3 C6 C9 131.2(3) . . ?
N2 C7 C6 114.9(3) . . ?
N2 C7 C11 117.1(3) . . ?
C6 C7 C11 127.9(3) . . ?
O1 C9 C6 125.4(4) . . ?
O1 C9 C10 116.1(3) . . ?
C6 C9 C10 118.4(3) . . ?
F1 C10 F2 107.3(3) . . ?
F1 C10 F3 107.6(4) . . ?
F2 C10 F3 107.2(4) . . ?
F1 C10 C9 111.6(4) . . ?
F2 C10 C9 112.1(3) . . ?
F3 C10 C9 110.8(3) . . ?
F6 C11 F5 106.6(3) . . ?
F6 C11 F4 106.5(3) . . ?
F5 C11 F4 106.1(3) . . ?
F6 C11 C7 111.5(3) . . ?
F5 C11 C7 114.0(3) . . ?
F4 C11 C7 111.7(3) . . ?
C5 N1 C1 121.4(3) . . ?
C5 N1 C8 119.9(3) . . ?
C1 N1 C8 118.7(3) . . ?
C7 N2 C4 104.3(3) . . ?

_refine_diff_density_max         0.176
_refine_diff_density_min         -0.191
_refine_diff_density_rms         0.045



####################################################################### 
# 
# 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_iv28
_audit_block_doi                 10.5517/ccdc.csd.cc2gfz52
_database_code_depnum_ccdc_archive 'CCDC 2277544'
loop_
_citation_id
_citation_doi
_citation_year
1 10.26434/chemrxiv-2023-qk7sx 2023
loop_
_audit_author_name
_audit_author_address
'E. Rusanov'
;ETH Zurich
Switzerland
;
_audit_update_record             
;
2023-06-28 deposited with the CCDC.	2024-02-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/4
_shelx_SHELXL_version_number     2016/4
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C11 H8 F6 N2 O2'
_chemical_formula_sum            'C11 H8 F6 N2 O2'
_chemical_formula_weight         314.19

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

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

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

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

_cell_length_a                   7.8422(5)
_cell_length_b                   8.9422(6)
_cell_length_c                   9.9332(7)
_cell_angle_alpha                68.876(5)
_cell_angle_beta                 83.817(5)
_cell_angle_gamma                65.104(5)
_cell_volume                     588.59(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    1349
_cell_measurement_theta_min      2.20
_cell_measurement_theta_max      22.91
_exptl_crystal_description       prizm
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.773
_exptl_crystal_F_000             316
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.185
_shelx_estimated_absorpt_T_min   0.947
_shelx_estimated_absorpt_T_max   0.982
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6153
_exptl_absorpt_correction_T_max  0.7453
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7585
_diffrn_reflns_av_unetI/netI     0.0747
_diffrn_reflns_av_R_equivalents  0.0621
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.201
_diffrn_reflns_theta_max         25.600
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2196
_reflns_number_gt                1414
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_refinement  'SHELXL-2016/4 (Sheldrick, 2016)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0484P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2196
_refine_ls_number_parameters     199
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0872
_refine_ls_R_factor_gt           0.0494
_refine_ls_wR_factor_ref         0.1173
_refine_ls_wR_factor_gt          0.1020
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_restrained_S_all      1.012
_refine_ls_shift/su_max          0.009
_refine_ls_shift/su_mean         0.001

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.0366(2) 0.5003(2) 0.75656(18) 0.0391(5) Uani 1 1 d . . . . .
F2 F 0.0724(2) 0.7423(2) 0.68599(19) 0.0386(5) Uani 1 1 d . . . . .
F3 F 0.2175(2) 0.5325(2) 0.88144(18) 0.0392(5) Uani 1 1 d . . . . .
F4 F 0.5959(2) 0.3860(2) 0.9229(2) 0.0480(5) Uani 1 1 d . . . . .
F5 F 0.8351(3) 0.2764(3) 0.80730(19) 0.0503(6) Uani 1 1 d . . . . .
F6 F 0.7842(2) 0.1181(2) 1.01395(19) 0.0412(5) Uani 1 1 d . . . . .
N1 N 0.3797(3) -0.1249(3) 0.6589(3) 0.0311(6) Uani 1 1 d . . . . .
N2 N 0.6409(3) 0.0167(3) 0.8379(2) 0.0242(6) Uani 1 1 d . . . . .
O1 O 0.2408(3) 0.5477(2) 0.5220(2) 0.0284(5) Uani 1 1 d . . . . .
O2 O 0.4605(3) 0.5633(3) 0.6485(2) 0.0282(5) Uani 1 1 d . . . . .
C1 C 0.2445(4) 0.0383(4) 0.5926(3) 0.0333(8) Uani 1 1 d . . . . .
H1 H 0.147800 0.047911 0.535780 0.040 Uiso 1 1 calc R U . . .
C2 C 0.2373(4) 0.1901(4) 0.6016(3) 0.0288(7) Uani 1 1 d . . . . .
H2 H 0.139490 0.301219 0.552825 0.035 Uiso 1 1 calc R U . . .
C3 C 0.3805(4) 0.1747(3) 0.6860(3) 0.0240(7) Uani 1 1 d . . . . .
C4 C 0.5171(4) 0.0050(3) 0.7582(3) 0.0240(7) Uani 1 1 d . . . . .
C5 C 0.5140(4) -0.1420(4) 0.7403(3) 0.0309(7) Uani 1 1 d . . . . .
H5 H 0.609563 -0.255430 0.787179 0.037 Uiso 1 1 calc R U . . .
C6 C 0.4288(4) 0.2946(3) 0.7219(3) 0.0225(6) Uani 1 1 d . . . . .
C7 C 0.5860(4) 0.1925(3) 0.8167(3) 0.0231(7) Uani 1 1 d . . . . .
C8 C 0.3292(4) 0.4942(3) 0.6559(3) 0.0231(7) Uani 1 1 d . . . . .
C9 C 0.1633(4) 0.5669(4) 0.7468(3) 0.0283(7) Uani 1 1 d . . . . .
C10 C 0.6985(4) 0.2450(4) 0.8882(3) 0.0295(7) Uani 1 1 d . . . . .
C11 C 0.8024(4) -0.1366(4) 0.9258(3) 0.0337(8) Uani 1 1 d . . . . .
H11A H 0.916957 -0.116120 0.900839 0.051 Uiso 1 1 calc R U . . .
H11B H 0.816649 -0.241363 0.906734 0.051 Uiso 1 1 calc R U . . .
H11C H 0.781271 -0.154693 1.028435 0.051 Uiso 1 1 calc R U . . .
H1O H 0.319(4) 0.515(4) 0.464(3) 0.042(10) Uiso 1 1 d . . . . .
H2O H 0.417(5) 0.670(4) 0.645(3) 0.048(11) Uiso 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
F1 C9 1.337(3) . ?
F2 C9 1.342(3) . ?
F3 C9 1.334(3) . ?
F4 C10 1.325(3) . ?
F5 C10 1.333(3) . ?
F6 C10 1.348(3) . ?
N1 C5 1.321(3) . ?
N1 C1 1.357(4) . ?
N2 C4 1.375(3) . ?
N2 C7 1.383(3) . ?
N2 C11 1.470(3) . ?
O1 C8 1.392(3) . ?
O2 C8 1.391(3) . ?
C1 C2 1.370(4) . ?
C2 C3 1.404(4) . ?
C3 C4 1.406(4) . ?
C3 C6 1.437(4) . ?
C4 C5 1.399(4) . ?
C6 C7 1.386(4) . ?
C6 C8 1.522(4) . ?
C7 C10 1.493(4) . ?
C8 C9 1.546(4) . ?

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
C5 N1 C1 118.7(2) . . ?
C4 N2 C7 107.9(2) . . ?
C4 N2 C11 123.4(2) . . ?
C7 N2 C11 128.6(2) . . ?
N1 C1 C2 124.7(3) . . ?
C1 C2 C3 117.3(3) . . ?
C2 C3 C4 117.8(2) . . ?
C2 C3 C6 135.7(3) . . ?
C4 C3 C6 106.4(2) . . ?
N2 C4 C5 130.2(3) . . ?
N2 C4 C3 109.2(2) . . ?
C5 C4 C3 120.5(3) . . ?
N1 C5 C4 120.8(3) . . ?
C7 C6 C3 106.5(2) . . ?
C7 C6 C8 129.0(2) . . ?
C3 C6 C8 124.3(2) . . ?
N2 C7 C6 109.9(2) . . ?
N2 C7 C10 119.6(2) . . ?
C6 C7 C10 130.4(2) . . ?
O2 C8 O1 112.6(2) . . ?
O2 C8 C6 108.1(2) . . ?
O1 C8 C6 111.7(2) . . ?
O2 C8 C9 110.9(2) . . ?
O1 C8 C9 102.8(2) . . ?
C6 C8 C9 110.8(2) . . ?
F3 C9 F1 107.1(2) . . ?
F3 C9 F2 107.2(2) . . ?
F1 C9 F2 106.9(2) . . ?
F3 C9 C8 113.0(2) . . ?
F1 C9 C8 111.7(2) . . ?
F2 C9 C8 110.7(2) . . ?
F4 C10 F5 107.5(2) . . ?
F4 C10 F6 104.8(2) . . ?
F5 C10 F6 106.0(2) . . ?
F4 C10 C7 113.5(2) . . ?
F5 C10 C7 112.6(2) . . ?
F6 C10 C7 111.9(2) . . ?

_refine_diff_density_max         0.260
_refine_diff_density_min         -0.249
_refine_diff_density_rms         0.062



####################################################################### 
# 
# 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_iv23
_audit_block_doi                 10.5517/ccdc.csd.cc2gfz41
_database_code_depnum_ccdc_archive 'CCDC 2277543'
loop_
_citation_id
_citation_doi
_citation_year
1 10.26434/chemrxiv-2023-qk7sx 2023
loop_
_audit_author_name
_audit_author_address
'E. Rusanov'
;ETH Zurich
Switzerland
;
_audit_update_record             
;
2023-06-28 deposited with the CCDC.	2024-02-08 downloaded from the CCDC.
;
# start Validation Reply Form

_vrf_PLAT420_iv23                
;
PROBLEM: D-H Bond Without Acceptor O4 --H4B . 
RESPONSE: H atom are located from DF synthesis of the electron density
and their position refined with restrained at 0.85A bond distances.
The O4 atom  of the solwate water molecule work as an acceptor 
for H3-O3. The H4a atom has the O1 atom as an acceptor and the second 
acceptor for H4b atom is absent, but possibly this H atom is disordered
over two position. 
;
# end Validation Reply Form

_audit_creation_date             2023-06-26
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C10 H8 Cl6 N2 O3, H2 O'
_chemical_formula_sum            'C10 H10 Cl6 N2 O4'
_chemical_formula_weight         434.90
_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'
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'
Cl Cl 0.1484 0.1585 '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                   10.9295(7)
_cell_length_b                   12.7056(8)
_cell_length_c                   13.4470(9)
_cell_angle_alpha                90
_cell_angle_beta                 112.199(4)
_cell_angle_gamma                90
_cell_volume                     1728.9(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1129
_cell_measurement_theta_min      2.57
_cell_measurement_theta_max      18.82
_cell_measurement_temperature    173(2)
_shelx_estimated_absorpt_T_max   0.897
_shelx_estimated_absorpt_T_min   0.809
_exptl_absorpt_coefficient_mu    1.008
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6311
_exptl_absorpt_correction_T_max  0.7453
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_exptl_crystal_description       prizm
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.671
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             872
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0988
_diffrn_reflns_av_unetI/netI     0.1021
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            14514
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.690
_diffrn_reflns_theta_min         2.012
_diffrn_ambient_temperature      173.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1892
_reflns_number_total             3290
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    ?
_refine_diff_density_max         0.855
_refine_diff_density_min         -0.454
_refine_diff_density_rms         0.097
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     215
_refine_ls_number_reflns         3290
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.1382
_refine_ls_R_factor_gt           0.0768
_refine_ls_restrained_S_all      1.027
_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)+(0.0749P)²+3.3855P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1688
_refine_ls_wR_factor_ref         0.1960
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All O(H) groups
2. Restrained distances
 O4-H4A = O4-H4B
 0.82 with sigma of 0.01
 N2-H2A
 0.9 with sigma of 0.01
3.a Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B)
3.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C4(H4), C5(H5)
3.c Tetrahedral OH refined with riding coordinates:
 O2(H2)
;
_atom_sites_solution_hydrogens   mixed
_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 0.6664(2) 0.5660(3) 0.10079(16) 0.0890(9) Uani 1 1 d . . . . .
Cl2 Cl 0.4707(2) 0.6583(3) 0.1654(2) 0.1100(11) Uani 1 1 d . . . . .
Cl3 Cl 0.5442(3) 0.4434(2) 0.2149(2) 0.1041(10) Uani 1 1 d . . . . .
Cl4 Cl 0.97963(17) 0.37169(13) 0.16904(13) 0.0441(5) Uani 1 1 d . . . . .
Cl5 Cl 1.15491(16) 0.49366(13) 0.09744(12) 0.0391(5) Uani 1 1 d . . . . .
Cl6 Cl 1.26098(18) 0.37490(14) 0.29345(14) 0.0492(5) Uani 1 1 d . . . . .
O1 O 0.6654(4) 0.6116(5) 0.3875(4) 0.0603(15) Uani 1 1 d . . . . .
O2 O 0.9884(4) 0.6010(3) 0.2100(3) 0.0292(10) Uani 1 1 d . . . . .
H2 H 0.996665 0.621874 0.153604 0.044 Uiso 1 1 calc R U . . .
O3 O 1.2074(5) 0.6205(3) 0.2942(3) 0.0337(10) Uani 1 1 d . . . . .
H3 H 1.284(5) 0.603(4) 0.342(4) 0.002(13) Uiso 1 1 d . . . . .
O4 O 0.4482(6) 0.5958(7) 0.4494(5) 0.0751(19) Uani 1 1 d D . . . .
H4A H 0.507(7) 0.576(9) 0.430(8) 0.12(4) Uiso 1 1 d D . . . .
H4B H 0.460(7) 0.658(2) 0.471(5) 0.03(2) Uiso 1 1 d D . . . .
N1 N 1.0160(5) 0.7539(4) 0.5755(4) 0.0305(12) Uani 1 1 d . . . . .
N2 N 0.8281(5) 0.6127(4) 0.3239(4) 0.0293(12) Uani 1 1 d D . . . .
H2A H 0.864(5) 0.604(4) 0.275(3) 0.024(15) Uiso 1 1 d D . . . .
C1 C 0.9168(6) 0.7196(5) 0.4882(5) 0.0271(14) Uani 1 1 d . . . . .
H1 H 0.830766 0.747398 0.472229 0.033 Uiso 1 1 calc R U . . .
C2 C 0.9356(6) 0.6438(5) 0.4193(4) 0.0256(13) Uani 1 1 d . . . . .
C3 C 1.0611(6) 0.6010(5) 0.4416(4) 0.0269(14) Uani 1 1 d . . . . .
C4 C 1.1626(6) 0.6396(5) 0.5324(5) 0.0316(15) Uani 1 1 d . . . . .
H4 H 1.250328 0.614624 0.550534 0.038 Uiso 1 1 calc R U . . .
C5 C 1.1359(6) 0.7147(5) 0.5967(5) 0.0336(15) Uani 1 1 d . . . . .
H5 H 1.206709 0.739203 0.658641 0.040 Uiso 1 1 calc R U . . .
C6 C 0.7059(6) 0.6003(5) 0.3159(5) 0.0406(17) Uani 1 1 d . . . . .
C7 C 0.6031(7) 0.5701(6) 0.2014(6) 0.051(2) Uani 1 1 d . . . . .
C8 C 1.0859(6) 0.5132(4) 0.3774(4) 0.0251(13) Uani 1 1 d . . . . .
H8A H 1.011168 0.462990 0.357676 0.030 Uiso 1 1 calc R U . . .
H8B H 1.166802 0.475068 0.422687 0.030 Uiso 1 1 calc R U . . .
C9 C 1.1024(6) 0.5509(5) 0.2743(5) 0.0290(14) Uani 1 1 d . . . . .
C10 C 1.1234(6) 0.4526(5) 0.2108(5) 0.0333(15) 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
Cl1 C7 1.737(7) . ?
Cl2 C7 1.748(8) . ?
Cl3 C7 1.768(8) . ?
Cl4 C10 1.781(6) . ?
Cl5 C10 1.764(6) . ?
Cl6 C10 1.792(6) . ?
O1 C6 1.210(7) . ?
O2 H2 0.8400 . ?
O2 C9 1.375(7) . ?
O3 H3 0.87(5) . ?
O3 C9 1.393(7) . ?
O4 H4A 0.819(10) . ?
O4 H4B 0.837(10) . ?
N1 C1 1.334(7) . ?
N1 C5 1.328(7) . ?
N2 H2A 0.898(10) . ?
N2 C2 1.429(7) . ?
N2 C6 1.309(8) . ?
C1 H1 0.9500 . ?
C1 C2 1.405(8) . ?
C2 C3 1.398(8) . ?
C3 C4 1.393(8) . ?
C3 C8 1.497(8) . ?
C4 H4 0.9500 . ?
C4 C5 1.390(8) . ?
C5 H5 0.9500 . ?
C6 C7 1.573(10) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C9 1.540(8) . ?
C9 C10 1.578(9) . ?

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
C9 O2 H2 109.5 . . ?
C9 O3 H3 118(3) . . ?
H4A O4 H4B 111(10) . . ?
C5 N1 C1 118.3(5) . . ?
C2 N2 H2A 105(3) . . ?
C6 N2 H2A 130(3) . . ?
C6 N2 C2 125.1(5) . . ?
N1 C1 H1 119.0 . . ?
N1 C1 C2 122.1(5) . . ?
C2 C1 H1 119.0 . . ?
C1 C2 N2 120.4(5) . . ?
C3 C2 N2 119.5(5) . . ?
C3 C2 C1 120.0(5) . . ?
C2 C3 C8 122.8(5) . . ?
C4 C3 C2 116.3(5) . . ?
C4 C3 C8 120.7(5) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 C3 120.1(6) . . ?
C5 C4 H4 119.9 . . ?
N1 C5 C4 123.1(6) . . ?
N1 C5 H5 118.5 . . ?
C4 C5 H5 118.5 . . ?
O1 C6 N2 126.1(6) . . ?
O1 C6 C7 117.9(6) . . ?
N2 C6 C7 116.0(6) . . ?
Cl1 C7 Cl2 109.6(4) . . ?
Cl1 C7 Cl3 108.7(4) . . ?
Cl2 C7 Cl3 108.4(4) . . ?
C6 C7 Cl1 115.0(5) . . ?
C6 C7 Cl2 108.9(5) . . ?
C6 C7 Cl3 105.9(5) . . ?
C3 C8 H8A 108.9 . . ?
C3 C8 H8B 108.9 . . ?
C3 C8 C9 113.3(5) . . ?
H8A C8 H8B 107.7 . . ?
C9 C8 H8A 108.9 . . ?
C9 C8 H8B 108.9 . . ?
O2 C9 O3 108.2(5) . . ?
O2 C9 C8 108.9(4) . . ?
O2 C9 C10 107.9(4) . . ?
O3 C9 C8 113.1(5) . . ?
O3 C9 C10 109.2(5) . . ?
C8 C9 C10 109.4(5) . . ?
Cl4 C10 Cl6 108.1(3) . . ?
Cl5 C10 Cl4 109.6(3) . . ?
Cl5 C10 Cl6 107.9(3) . . ?
C9 C10 Cl4 109.6(4) . . ?
C9 C10 Cl5 110.5(4) . . ?
C9 C10 Cl6 111.1(4) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O2 H2 N1 0.84 1.95 2.679(6) 144.3 4_575 yes
O3 H3 O4 0.87(5) 1.83(5) 2.689(8) 168(4) 1_655 yes
O4 H4A O1 0.819(10) 2.07(6) 2.804(8) 150(11) . yes
N2 H2A O2 0.898(10) 1.87(2) 2.732(6) 161(5) . yes

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 C6 C7 Cl1 174.9(6) . . . . ?
O1 C6 C7 Cl2 51.4(8) . . . . ?
O1 C6 C7 Cl3 -65.0(8) . . . . ?
O2 C9 C10 Cl4 -54.8(5) . . . . ?
O2 C9 C10 Cl5 66.1(5) . . . . ?
O2 C9 C10 Cl6 -174.3(4) . . . . ?
O3 C9 C10 Cl4 -172.2(4) . . . . ?
O3 C9 C10 Cl5 -51.3(5) . . . . ?
O3 C9 C10 Cl6 68.4(5) . . . . ?
N1 C1 C2 N2 -177.1(5) . . . . ?
N1 C1 C2 C3 0.6(8) . . . . ?
N2 C2 C3 C4 176.3(5) . . . . ?
N2 C2 C3 C8 -8.0(8) . . . . ?
N2 C6 C7 Cl1 -4.0(9) . . . . ?
N2 C6 C7 Cl2 -127.4(6) . . . . ?
N2 C6 C7 Cl3 116.1(6) . . . . ?
C1 N1 C5 C4 -0.2(9) . . . . ?
C1 C2 C3 C4 -1.4(8) . . . . ?
C1 C2 C3 C8 174.3(5) . . . . ?
C2 N2 C6 O1 -1.2(11) . . . . ?
C2 N2 C6 C7 177.6(6) . . . . ?
C2 C3 C4 C5 1.5(8) . . . . ?
C2 C3 C8 C9 83.3(7) . . . . ?
C3 C4 C5 N1 -0.7(9) . . . . ?
C3 C8 C9 O2 -60.4(6) . . . . ?
C3 C8 C9 O3 59.8(7) . . . . ?
C3 C8 C9 C10 -178.2(5) . . . . ?
C4 C3 C8 C9 -101.1(6) . . . . ?
C5 N1 C1 C2 0.3(8) . . . . ?
C6 N2 C2 C1 -38.3(9) . . . . ?
C6 N2 C2 C3 144.0(6) . . . . ?
C8 C3 C4 C5 -174.3(5) . . . . ?
C8 C9 C10 Cl4 63.5(5) . . . . ?
C8 C9 C10 Cl5 -175.6(4) . . . . ?
C8 C9 C10 Cl6 -56.0(6) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_iv29_sq
_audit_block_doi                 10.5517/ccdc.csd.cc2gfz63
_database_code_depnum_ccdc_archive 'CCDC 2277545'
loop_
_citation_id
_citation_doi
_citation_year
1 10.26434/chemrxiv-2023-qk7sx 2023
loop_
_audit_author_name
_audit_author_address
'E. Rusanov'
;ETH Zurich
Switzerland
;
_audit_update_record             
;
2023-06-28 deposited with the CCDC.	2024-02-08 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT420_iv29_sq             
;
PROBLEM: Bond Without Acceptor O1 --H1O . 
RESPONSE: there is no acceptor for the hydrogen bond OH...A, because the 
data were processed using a SQUEEZE procedure for a barely disordered in
cavity solvated MTBE molecule. Thus, the H atom is directed into the 
cavities, but the MTBE acceptor molecule is absent.
 
;
# end Validation Reply Form

_audit_creation_date             2023-06-26
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C11 H9 F6 N2 O2, C2 F3 O2, C5 H12 O'
_chemical_formula_sum            'C18 H21 F9 N2 O5'
_chemical_formula_weight         516.37
_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'

_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           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   35.604(2)
_cell_length_b                   6.8088(4)
_cell_length_c                   21.8140(13)
_cell_angle_alpha                90
_cell_angle_beta                 120.757(3)
_cell_angle_gamma                90
_cell_volume                     4544.4(5)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    4422
_cell_measurement_temperature    173.15
_cell_measurement_theta_max      22.41
_cell_measurement_theta_min      2.17
_shelx_estimated_absorpt_T_max   0.989
_shelx_estimated_absorpt_T_min   0.919
_exptl_absorpt_coefficient_mu    0.156
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.5986
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1316 before and 0.0477 after correction.
The Ratio of minimum to maximum transmission is 0.8033.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.509
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             2112
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.07
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0375
_diffrn_reflns_av_unetI/netI     0.0516
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       41
_diffrn_reflns_limit_h_min       -42
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            13257
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        24.940
_diffrn_reflns_theta_max         24.940
_diffrn_reflns_theta_min         1.331
_diffrn_ambient_temperature      173.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           30.0
_diffrn_source_power             1.2
_diffrn_source_voltage           40.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2732
_reflns_number_total             3947
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    ?
_refine_diff_density_max         0.651
_refine_diff_density_min         -0.522
_refine_diff_density_rms         0.108
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.979
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     321
_refine_ls_number_reflns         3947
_refine_ls_number_restraints     56
_refine_ls_R_factor_all          0.0843
_refine_ls_R_factor_gt           0.0627
_refine_ls_restrained_S_all      1.093
_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)+(0.1687P)²+1.0045P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1987
_refine_ls_wR_factor_ref         0.2280
_refine_special_details          SQUEEZE
_olex2_refinement_description    
;
# SQUEEZE RESULTS (Version = 290122)
# Note: Data are Listed for all Voids in the P1 Unit Cell
# i.e. Centre of Gravity, Solvent Accessible Volume,
# Recovered number of Electrons in the Void and
# Details about the Squeezed Material
loop_
  _platon_squeeze_void_nr
  _platon_squeeze_void_average_x
  _platon_squeeze_void_average_y
  _platon_squeeze_void_average_z
  _platon_squeeze_void_volume
  _platon_squeeze_void_count_electrons
  _platon_squeeze_void_content
   1  0.250 -0.074  0.500       372       142 ' '
   2  0.250 -0.031  1.000       371       142 ' '
   3  0.750 -0.039  0.500       372       142 ' '
   4  0.750 -0.034  1.000       371       142 ' '
_platon_squeeze_void_probe_radius                  1.20
_platon_squeeze_details                           ?

1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C13-F7A = C13-F7B = C13-F8A = C13-F8B = C13-F9A = C13-F9B
 1.33 with sigma of 0.005
 C9-F1A = C9-F2B = C9-F3A = C9-F1B = C9-F2A = C9-F3B
 1.33 with sigma of 0.005
 O1-H1B = O2-H2A
 0.85 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
Uanis(F8A) \\sim Ueq, Uanis(F7A) \\sim Ueq, Uanis(F7B) \\sim Ueq, Uanis(F9A)
\\sim Ueq, Uanis(F9B) \\sim Ueq, Uanis(F8B) \\sim Ueq, Uanis(F3A) \\sim Ueq:
with sigma of 0.005 and sigma for terminal atoms of 0.005
4. Others
 Sof(F1B)=Sof(F2B)=Sof(F3B)=Sof(F7B)=Sof(F8B)=Sof(F9B)=1-FVAR(1)
 Sof(F1A)=Sof(F2A)=Sof(F3A)=Sof(F7A)=Sof(F8A)=Sof(F9A)=FVAR(1)
5.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C5(H5)
5.b Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C)
;
_atom_sites_solution_hydrogens   mixed
_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
C1 C -0.01669(10) 0.0458(4) 0.07930(14) 0.0339(7) Uani 1 1 d . . . . .
H1 H -0.046561 0.052900 0.042668 0.041 Uiso 1 1 calc R U . . .
C2 C 0.01358(9) 0.1546(4) 0.07361(14) 0.0315(7) Uani 1 1 d . . . . .
H2 H 0.005164 0.235894 0.033226 0.038 Uiso 1 1 calc R U . . .
C3 C 0.05764(9) 0.1434(4) 0.12902(13) 0.0285(6) Uani 1 1 d . . . . .
C4 C 0.06788(9) 0.0212(4) 0.18790(14) 0.0301(7) Uani 1 1 d . . . . .
C5 C 0.03620(10) -0.0887(4) 0.19098(15) 0.0345(7) Uani 1 1 d . . . . .
H5 H 0.043381 -0.172418 0.230324 0.041 Uiso 1 1 calc R U . . .
C6 C 0.09721(9) 0.2363(4) 0.14286(14) 0.0291(6) Uani 1 1 d . . . . .
C7 C 0.12918(9) 0.1693(4) 0.20969(15) 0.0326(7) Uani 1 1 d . . . . .
C8 C 0.13415(12) -0.0817(5) 0.30161(16) 0.0464(8) Uani 1 1 d . . . . .
H8A H 0.160174 -0.142201 0.305184 0.070 Uiso 1 1 calc R U . . .
H8B H 0.114413 -0.184599 0.299962 0.070 Uiso 1 1 calc R U . . .
H8C H 0.142874 0.002423 0.343236 0.070 Uiso 1 1 calc R U . . .
C9 C 0.17610(10) 0.2232(4) 0.25532(15) 0.0483(9) Uani 1 1 d D . . . .
C10 C 0.09994(9) 0.3815(4) 0.09254(15) 0.0320(7) Uani 1 1 d . . . . .
C11 C 0.08832(10) 0.5862(5) 0.10659(15) 0.0372(7) Uani 1 1 d . . . . .
C12 C 0.06410(10) 0.5312(5) 0.36357(15) 0.0365(7) Uani 1 1 d . . . . .
C13 C 0.07265(12) 0.3845(4) 0.31966(17) 0.0567(10) Uani 1 1 d D . . . .
F1A F 0.1803(5) 0.4164(8) 0.2580(8) 0.050(3) Uani 0.238(7) 1 d D . P A 1
F2A F 0.1990(4) 0.1435(18) 0.2296(6) 0.050(3) Uani 0.238(7) 1 d D . P A 1
F3A F 0.1942(4) 0.1624(17) 0.3217(4) 0.050(3) Uani 0.238(7) 1 d D U P A 1
F1B F 0.18961(18) 0.3778(8) 0.2362(3) 0.101(2) Uani 0.762(7) 1 d D . P A 2
F2B F 0.20241(15) 0.0780(8) 0.2625(4) 0.112(2) Uani 0.762(7) 1 d D . P A 2
F3B F 0.18652(16) 0.2614(11) 0.32160(17) 0.098(2) Uani 0.762(7) 1 d D . P A 2
F4 F 0.04880(6) 0.5895(3) 0.09980(10) 0.0497(5) Uani 1 1 d . . . . .
F5 F 0.08733(7) 0.7195(3) 0.06094(10) 0.0530(5) Uani 1 1 d . . . . .
F6 F 0.11693(7) 0.6520(3) 0.17177(9) 0.0532(5) Uani 1 1 d . . . . .
F7A F 0.0338(3) 0.339(3) 0.2617(7) 0.129(7) Uani 0.238(7) 1 d D U P A 1
F8A F 0.0859(5) 0.2076(12) 0.3480(7) 0.072(4) Uani 0.238(7) 1 d D U P A 1
F9A F 0.0857(5) 0.4455(15) 0.2774(6) 0.068(4) Uani 0.238(7) 1 d D U P A 1
F7B F 0.0515(2) 0.4242(6) 0.25007(16) 0.0965(16) Uani 0.762(7) 1 d D U P A 2
F8B F 0.06300(18) 0.2005(4) 0.3247(2) 0.0600(11) Uani 0.762(7) 1 d D U P A 2
F9B F 0.11515(13) 0.3882(6) 0.3395(3) 0.1057(18) Uani 0.762(7) 1 d D U P A 2
N1 N -0.00472(9) -0.0726(4) 0.13673(13) 0.0339(6) Uani 1 1 d . . . . .
N2 N 0.11168(8) 0.0371(3) 0.23640(12) 0.0331(6) Uani 1 1 d . . . . .
O1 O 0.06831(7) 0.3233(3) 0.02383(10) 0.0392(5) Uani 1 1 d D . . . .
H1B H 0.0709(14) 0.394(5) -0.0064(17) 0.074(13) Uiso 1 1 d D . . . .
O2 O 0.14080(7) 0.4019(4) 0.10072(13) 0.0483(6) Uani 1 1 d D . . . .
H2A H 0.1506(17) 0.303(5) 0.089(3) 0.102(19) Uiso 1 1 d D . . . .
O3 O 0.05658(7) 0.7021(3) 0.33887(11) 0.0403(6) Uani 1 1 d . . . . .
O4 O 0.06557(9) 0.4655(3) 0.41706(11) 0.0523(7) Uani 1 1 d . . . . .
H1A H -0.0264(11) -0.144(5) 0.1411(16) 0.040(9) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 H1 0.9500 . ?
C1 C2 1.364(4) . ?
C1 N1 1.362(4) . ?
C2 H2 0.9500 . ?
C2 C3 1.410(4) . ?
C3 C4 1.413(4) . ?
C3 C6 1.429(4) . ?
C4 C5 1.384(4) . ?
C4 N2 1.369(4) . ?
C5 H5 0.9500 . ?
C5 N1 1.331(4) . ?
C6 C7 1.390(4) . ?
C6 C10 1.517(4) . ?
C7 C9 1.488(4) . ?
C7 N2 1.381(4) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C8 N2 1.468(4) . ?
C9 F1A 1.322(5) . ?
C9 F2A 1.321(5) . ?
C9 F3A 1.315(5) . ?
C9 F1B 1.311(4) . ?
C9 F2B 1.315(4) . ?
C9 F3B 1.322(4) . ?
C10 C11 1.528(4) . ?
C10 O1 1.395(3) . ?
C10 O2 1.379(4) . ?
C11 F4 1.338(4) . ?
C11 F5 1.334(4) . ?
C11 F6 1.334(3) . ?
C12 C13 1.519(4) . ?
C12 O3 1.252(4) . ?
C12 O4 1.225(4) . ?
C13 F7A 1.349(5) . ?
C13 F8A 1.326(5) . ?
C13 F9A 1.296(5) . ?
C13 F7B 1.332(4) . ?
C13 F8B 1.319(4) . ?
C13 F9B 1.344(4) . ?
N1 H1A 0.96(3) . ?
O1 H1B 0.857(10) . ?
O2 H2A 0.853(10) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 H1 119.5 . . ?
N1 C1 H1 119.5 . . ?
N1 C1 C2 121.0(3) . . ?
C1 C2 H2 120.8 . . ?
C1 C2 C3 118.5(3) . . ?
C3 C2 H2 120.8 . . ?
C2 C3 C4 117.9(3) . . ?
C2 C3 C6 134.6(3) . . ?
C4 C3 C6 107.5(2) . . ?
C5 C4 C3 121.7(3) . . ?
N2 C4 C3 108.6(2) . . ?
N2 C4 C5 129.8(3) . . ?
C4 C5 H5 121.3 . . ?
N1 C5 C4 117.5(3) . . ?
N1 C5 H5 121.3 . . ?
C3 C6 C10 123.8(2) . . ?
C7 C6 C3 105.5(2) . . ?
C7 C6 C10 130.7(3) . . ?
C6 C7 C9 131.1(3) . . ?
N2 C7 C6 110.6(2) . . ?
N2 C7 C9 118.2(2) . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N2 C8 H8A 109.5 . . ?
N2 C8 H8B 109.5 . . ?
N2 C8 H8C 109.5 . . ?
F1A C9 C7 109.8(7) . . ?
F2A C9 C7 109.9(6) . . ?
F2A C9 F1A 110.2(8) . . ?
F3A C9 C7 114.1(7) . . ?
F3A C9 F1A 106.5(8) . . ?
F3A C9 F2A 106.1(7) . . ?
F1B C9 C7 117.0(3) . . ?
F1B C9 F2B 106.6(4) . . ?
F1B C9 F3B 104.3(4) . . ?
F2B C9 C7 112.4(3) . . ?
F2B C9 F3B 103.5(4) . . ?
F3B C9 C7 111.8(3) . . ?
C6 C10 C11 109.0(2) . . ?
O1 C10 C6 106.1(2) . . ?
O1 C10 C11 108.8(2) . . ?
O2 C10 C6 115.2(2) . . ?
O2 C10 C11 105.0(2) . . ?
O2 C10 O1 112.7(2) . . ?
F4 C11 C10 111.8(2) . . ?
F5 C11 C10 112.1(2) . . ?
F5 C11 F4 106.3(2) . . ?
F6 C11 C10 112.5(3) . . ?
F6 C11 F4 107.4(2) . . ?
F6 C11 F5 106.3(2) . . ?
O3 C12 C13 114.1(2) . . ?
O4 C12 C13 115.9(3) . . ?
O4 C12 O3 130.1(3) . . ?
F7A C13 C12 107.5(8) . . ?
F8A C13 C12 116.3(7) . . ?
F8A C13 F7A 100.3(10) . . ?
F9A C13 C12 120.0(5) . . ?
F9A C13 F7A 88.7(10) . . ?
F9A C13 F8A 116.7(9) . . ?
F7B C13 C12 114.0(3) . . ?
F7B C13 F9B 104.5(4) . . ?
F8B C13 C12 115.3(3) . . ?
F8B C13 F7B 105.5(4) . . ?
F8B C13 F9B 106.8(4) . . ?
F9B C13 C12 109.9(3) . . ?
C1 N1 H1A 120(2) . . ?
C5 N1 C1 123.5(3) . . ?
C5 N1 H1A 116.1(19) . . ?
C4 N2 C7 107.9(2) . . ?
C4 N2 C8 123.1(3) . . ?
C7 N2 C8 128.9(3) . . ?
C10 O1 H1B 109(3) . . ?
C10 O2 H2A 116(4) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 C2 C3 C4 -0.6(4) . . . . ?
C1 C2 C3 C6 -177.9(3) . . . . ?
C2 C1 N1 C5 1.2(4) . . . . ?
C2 C3 C4 C5 1.6(4) . . . . ?
C2 C3 C4 N2 -177.7(2) . . . . ?
C2 C3 C6 C7 176.3(3) . . . . ?
C2 C3 C6 C10 -1.8(5) . . . . ?
C3 C4 C5 N1 -1.1(4) . . . . ?
C3 C4 N2 C7 0.8(3) . . . . ?
C3 C4 N2 C8 -175.2(3) . . . . ?
C3 C6 C7 C9 -175.1(3) . . . . ?
C3 C6 C7 N2 1.7(3) . . . . ?
C3 C6 C10 C11 84.6(3) . . . . ?
C3 C6 C10 O1 -32.4(4) . . . . ?
C3 C6 C10 O2 -157.8(3) . . . . ?
C4 C3 C6 C7 -1.2(3) . . . . ?
C4 C3 C6 C10 -179.2(2) . . . . ?
C4 C5 N1 C1 -0.3(4) . . . . ?
C5 C4 N2 C7 -178.4(3) . . . . ?
C5 C4 N2 C8 5.6(5) . . . . ?
C6 C3 C4 C5 179.5(2) . . . . ?
C6 C3 C4 N2 0.2(3) . . . . ?
C6 C7 C9 F1A 46.4(8) . . . . ?
C6 C7 C9 F2A -75.1(7) . . . . ?
C6 C7 C9 F3A 165.8(7) . . . . ?
C6 C7 C9 F1B 11.0(6) . . . . ?
C6 C7 C9 F2B -112.9(5) . . . . ?
C6 C7 C9 F3B 131.1(5) . . . . ?
C6 C7 N2 C4 -1.6(3) . . . . ?
C6 C7 N2 C8 174.1(3) . . . . ?
C6 C10 C11 F4 -56.7(3) . . . . ?
C6 C10 C11 F5 -176.0(2) . . . . ?
C6 C10 C11 F6 64.2(3) . . . . ?
C7 C6 C10 C11 -93.0(4) . . . . ?
C7 C6 C10 O1 150.1(3) . . . . ?
C7 C6 C10 O2 24.6(4) . . . . ?
C9 C7 N2 C4 175.7(2) . . . . ?
C9 C7 N2 C8 -8.7(4) . . . . ?
C10 C6 C7 C9 2.8(5) . . . . ?
C10 C6 C7 N2 179.6(3) . . . . ?
N1 C1 C2 C3 -0.7(4) . . . . ?
N2 C4 C5 N1 178.0(3) . . . . ?
N2 C7 C9 F1A -130.3(7) . . . . ?
N2 C7 C9 F2A 108.3(6) . . . . ?
N2 C7 C9 F3A -10.8(7) . . . . ?
N2 C7 C9 F1B -165.6(5) . . . . ?
N2 C7 C9 F2B 70.5(5) . . . . ?
N2 C7 C9 F3B -45.5(5) . . . . ?
O1 C10 C11 F4 58.5(3) . . . . ?
O1 C10 C11 F5 -60.7(3) . . . . ?
O1 C10 C11 F6 179.4(2) . . . . ?
O2 C10 C11 F4 179.4(2) . . . . ?
O2 C10 C11 F5 60.1(3) . . . . ?
O2 C10 C11 F6 -59.7(3) . . . . ?
O3 C12 C13 F7A -76.5(11) . . . . ?
O3 C12 C13 F8A 172.1(9) . . . . ?
O3 C12 C13 F9A 22.4(9) . . . . ?
O3 C12 C13 F7B -30.9(5) . . . . ?
O3 C12 C13 F8B -153.2(4) . . . . ?
O3 C12 C13 F9B 86.0(4) . . . . ?
O4 C12 C13 F7A 103.5(11) . . . . ?
O4 C12 C13 F8A -7.9(9) . . . . ?
O4 C12 C13 F9A -157.6(8) . . . . ?
O4 C12 C13 F7B 149.1(4) . . . . ?
O4 C12 C13 F8B 26.8(5) . . . . ?
O4 C12 C13 F9B -94.0(4) . . . . ?

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 0.250 -0.353 -0.249 755.0 295.2 '4 C5H12O'
2 0.750 -0.080 -0.526 755.0 295.2 '4 C5H12O'

_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_iv31
_audit_block_doi                 10.5517/ccdc.csd.cc2gfz74
_database_code_depnum_ccdc_archive 'CCDC 2277546'
loop_
_citation_id
_citation_doi
_citation_year
1 10.26434/chemrxiv-2023-qk7sx 2023
loop_
_audit_author_name
_audit_author_address
'E. Rusanov'
;ETH Zurich
Switzerland
;
_audit_update_record             
;
2023-06-28 deposited with the CCDC.	2024-02-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/4
_shelx_SHELXL_version_number     2016/4
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H10 F6 N2 O2'
_chemical_formula_sum            'C12 H10 F6 N2 O2'
_chemical_formula_weight         328.22

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

_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                   10.4771(8)
_cell_length_b                   15.0099(13)
_cell_length_c                   8.5190(7)
_cell_angle_alpha                90
_cell_angle_beta                 99.894(5)
_cell_angle_gamma                90
_cell_volume                     1319.77(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2040
_cell_measurement_theta_min      2.39
_cell_measurement_theta_max      24.93
_exptl_crystal_description       prizm
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.652
_exptl_crystal_F_000             664
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.370
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.070
_exptl_absorpt_coefficient_mu    0.169
_shelx_estimated_absorpt_T_min   0.940
_shelx_estimated_absorpt_T_max   0.988
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5843
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10450
_diffrn_reflns_av_unetI/netI     0.0799
_diffrn_reflns_av_R_equivalents  0.0686
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         1.973
_diffrn_reflns_theta_max         25.035
_diffrn_reflns_theta_full        25.035
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measured_fraction_theta_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_point_group_measured_fraction_full 0.985
_reflns_number_total             2294
_reflns_number_gt                1450
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2016/4 (Sheldrick, 2016)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0787P)²+1.7985P] 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         2294
_refine_ls_number_parameters     201
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1232
_refine_ls_R_factor_gt           0.0712
_refine_ls_wR_factor_ref         0.1880
_refine_ls_wR_factor_gt          0.1674
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_restrained_S_all      1.059
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.4765(5) 0.2532(3) 0.3454(6) 0.0392(13) Uani 1 1 d . . . . .
H1 H 0.397307 0.250794 0.380544 0.047 Uiso 1 1 calc R U . . .
C2 C 0.5313(4) 0.3354(3) 0.3342(6) 0.0323(12) Uani 1 1 d . . . . .
H2 H 0.489940 0.387059 0.359125 0.039 Uiso 1 1 calc R U . . .
C3 C 0.6518(4) 0.3391(3) 0.2838(5) 0.0271(11) Uani 1 1 d . . . . .
C4 C 0.7083(4) 0.2575(3) 0.2527(5) 0.0275(11) Uani 1 1 d . . . . .
C5 C 0.6448(5) 0.1772(3) 0.2650(6) 0.0321(12) Uani 1 1 d . . . . .
H5 H 0.683656 0.124087 0.242205 0.039 Uiso 1 1 calc R U . . .
C6 C 0.7395(4) 0.4082(3) 0.2544(5) 0.0251(10) Uani 1 1 d . . . . .
C7 C 0.8455(4) 0.3653(3) 0.2108(5) 0.0237(10) Uani 1 1 d . . . . .
C8 C 0.9082(5) 0.2038(3) 0.1554(6) 0.0338(12) Uani 1 1 d . . . . .
H8A H 0.944497 0.225114 0.066313 0.051 Uiso 1 1 calc R U . . .
H8B H 0.856511 0.151876 0.124196 0.051 Uiso 1 1 calc R U . . .
H8C H 0.976916 0.188723 0.241122 0.051 Uiso 1 1 calc R U . . .
C9 C 0.9694(5) 0.3974(3) 0.1679(6) 0.0337(12) Uani 1 1 d . . . . .
C10 C 0.7079(4) 0.5079(3) 0.2605(6) 0.0297(11) Uani 1 1 d . . . . .
C11 C 0.7662(5) 0.5484(3) 0.4220(6) 0.0340(12) Uani 1 1 d . . . . .
F1 F 1.0715(3) 0.35206(18) 0.2482(4) 0.0454(8) Uani 1 1 d . . . . .
F2 F 0.9723(3) 0.3848(2) 0.0135(3) 0.0563(9) Uani 1 1 d . . . . .
F3 F 0.9937(3) 0.48245(16) 0.2001(3) 0.0435(8) Uani 1 1 d . . . . .
F4 F 0.7283(3) 0.50361(18) 0.5423(3) 0.0514(9) Uani 1 1 d . . . . .
F5 F 0.7288(3) 0.63252(16) 0.4349(4) 0.0474(8) Uani 1 1 d . . . . .
F6 F 0.8957(3) 0.54829(19) 0.4503(3) 0.0478(8) Uani 1 1 d . . . . .
N1 N 0.5296(4) 0.1754(2) 0.3089(5) 0.0380(11) Uani 1 1 d . . . . .
N2 N 0.8267(3) 0.2736(2) 0.2082(4) 0.0268(9) Uani 1 1 d . . . . .
O1 O 0.5752(3) 0.51386(19) 0.2413(4) 0.0376(9) Uani 1 1 d . . . . .
H1A H 0.553884 0.566361 0.243250 0.056 Uiso 1 1 calc R U . . .
O2 O 0.7609(3) 0.56077(19) 0.1521(4) 0.0328(8) Uani 1 1 d . . . . .
C12 C 0.7039(6) 0.5464(4) -0.0119(7) 0.0555(16) Uani 1 1 d . . . . .
H12A H 0.710817 0.484500 -0.037808 0.083 Uiso 1 1 calc R U . . .
H12B H 0.748561 0.581708 -0.079211 0.083 Uiso 1 1 calc R U . . .
H12C H 0.614186 0.563260 -0.028219 0.083 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.353(6) . ?
C1 C2 1.371(6) . ?
C2 C3 1.403(6) . ?
C3 C4 1.406(6) . ?
C3 C6 1.435(6) . ?
C4 N2 1.380(5) . ?
C4 C5 1.389(6) . ?
C5 N1 1.324(6) . ?
C6 C7 1.388(6) . ?
C6 C10 1.536(6) . ?
C7 N2 1.390(5) . ?
C7 C9 1.488(6) . ?
C8 N2 1.471(5) . ?
C9 F3 1.321(5) . ?
C9 F2 1.334(5) . ?
C9 F1 1.351(5) . ?
C10 O1 1.375(5) . ?
C10 O2 1.402(5) . ?
C10 C11 1.531(7) . ?
C11 F5 1.332(5) . ?
C11 F6 1.336(5) . ?
C11 F4 1.341(5) . ?
O2 C12 1.439(6) . ?

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
N1 C1 C2 124.6(4) . . ?
C1 C2 C3 117.8(4) . . ?
C2 C3 C4 117.0(4) . . ?
C2 C3 C6 135.9(4) . . ?
C4 C3 C6 107.1(4) . . ?
N2 C4 C5 129.7(4) . . ?
N2 C4 C3 109.0(4) . . ?
C5 C4 C3 121.3(4) . . ?
N1 C5 C4 120.7(4) . . ?
C7 C6 C3 106.1(4) . . ?
C7 C6 C10 130.3(4) . . ?
C3 C6 C10 123.4(4) . . ?
C6 C7 N2 110.2(4) . . ?
C6 C7 C9 133.5(4) . . ?
N2 C7 C9 116.3(4) . . ?
F3 C9 F2 107.8(4) . . ?
F3 C9 F1 105.9(4) . . ?
F2 C9 F1 106.1(4) . . ?
F3 C9 C7 114.0(4) . . ?
F2 C9 C7 111.4(4) . . ?
F1 C9 C7 111.2(4) . . ?
O1 C10 O2 113.0(4) . . ?
O1 C10 C11 108.7(4) . . ?
O2 C10 C11 103.0(3) . . ?
O1 C10 C6 106.2(3) . . ?
O2 C10 C6 114.7(4) . . ?
C11 C10 C6 111.2(4) . . ?
F5 C11 F6 106.9(4) . . ?
F5 C11 F4 106.4(4) . . ?
F6 C11 F4 106.6(4) . . ?
F5 C11 C10 111.8(4) . . ?
F6 C11 C10 113.4(4) . . ?
F4 C11 C10 111.2(4) . . ?
C5 N1 C1 118.6(4) . . ?
C4 N2 C7 107.5(3) . . ?
C4 N2 C8 123.7(4) . . ?
C7 N2 C8 128.5(4) . . ?
C10 O2 C12 114.2(4) . . ?

_refine_diff_density_max         0.237
_refine_diff_density_min         -0.235
_refine_diff_density_rms         0.060



