# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 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_v26
_audit_block_doi                 10.5517/ccdc.csd.cc2gr9r9
_database_code_depnum_ccdc_archive 'CCDC 2286521'
loop_
_citation_id
_citation_doi
_citation_year
1 10.26434/chemrxiv-2023-78z7p 2023
loop_
_audit_author_name
_audit_author_address
'Iryna Sadkova'
;Enamine Ltd
Ukraine
;
_audit_update_record             
;
2023-08-03 deposited with the CCDC.	2023-10-27 downloaded from the CCDC.
;
_audit_creation_date             2022-08-19
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C13 H13 F O2'
_chemical_formula_sum            'C13 H13 F O2'
_chemical_formula_weight         220.23
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   12.625(3)
_cell_length_b                   6.2763(14)
_cell_length_c                   14.050(3)
_cell_angle_alpha                90
_cell_angle_beta                 95.590(14)
_cell_angle_gamma                90
_cell_volume                     1108.0(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2379
_cell_measurement_temperature    273.15
_cell_measurement_theta_max      20.66
_cell_measurement_theta_min      2.91
_shelx_estimated_absorpt_T_max   0.990
_shelx_estimated_absorpt_T_min   0.980
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.320
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             464
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0520
_diffrn_reflns_av_unetI/netI     0.0351
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            13942
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        24.996
_diffrn_reflns_theta_max         24.996
_diffrn_reflns_theta_min         2.071
_diffrn_ambient_temperature      273.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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                1370
_reflns_number_total             1955
_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 2016/6 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.159
_refine_diff_density_min         -0.177
_refine_diff_density_rms         0.039
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     146
_refine_ls_number_reflns         1955
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0744
_refine_ls_R_factor_gt           0.0474
_refine_ls_restrained_S_all      1.023
_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)+(0.0547P)²+0.3550P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1097
_refine_ls_wR_factor_ref         0.1263
_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.a Ternary CH refined with riding coordinates:
 C4(H4)
2.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C5(H5A,H5B), C6(H6A,H6B)
2.c Aromatic/amide H refined with riding coordinates:
 C9(H9), C10(H10), C11(H11), C12(H12), C13(H13)
2.d Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.29331(10) 0.01109(19) 0.51394(9) 0.0601(4) Uani 1 1 d . . . . .
O1 O 0.43683(13) 0.2630(3) 0.47120(14) 0.0781(6) Uani 1 1 d . . . . .
H1 H 0.486252 0.344599 0.464326 0.117 Uiso 1 1 calc R U . . .
O2 O 0.39495(12) 0.5190(3) 0.56918(12) 0.0684(5) Uani 1 1 d . . . . .
C1 C 0.28411(16) 0.2129(3) 0.55449(14) 0.0450(5) Uani 1 1 d . . . . .
C2 C 0.17497(15) 0.3089(3) 0.51898(13) 0.0420(5) Uani 1 1 d . . . . .
C3 C 0.10149(17) 0.1610(4) 0.57301(15) 0.0571(6) Uani 1 1 d . . . . .
H3A H 0.026014 0.191104 0.560999 0.069 Uiso 1 1 calc R U . . .
H3B H 0.116407 0.009915 0.568327 0.069 Uiso 1 1 calc R U . . .
C4 C 0.15756(18) 0.2717(4) 0.66169(15) 0.0619(7) Uani 1 1 d . . . . .
H4 H 0.123531 0.275088 0.721455 0.074 Uiso 1 1 calc R U . . .
C5 C 0.27191(18) 0.1931(4) 0.66200(15) 0.0619(7) Uani 1 1 d . . . . .
H5A H 0.279788 0.047039 0.684126 0.074 Uiso 1 1 calc R U . . .
H5B H 0.321705 0.283737 0.700171 0.074 Uiso 1 1 calc R U . . .
C6 C 0.15836(18) 0.4725(4) 0.59945(15) 0.0559(6) Uani 1 1 d . . . . .
H6A H 0.218028 0.567447 0.615633 0.067 Uiso 1 1 calc R U . . .
H6B H 0.091325 0.548977 0.591360 0.067 Uiso 1 1 calc R U . . .
C7 C 0.37960(15) 0.3400(3) 0.52942(14) 0.0450(5) Uani 1 1 d . . . . .
C8 C 0.15188(14) 0.3550(3) 0.41469(14) 0.0418(5) Uani 1 1 d . . . . .
C9 C 0.17145(17) 0.5525(4) 0.37673(16) 0.0561(6) Uani 1 1 d . . . . .
H9 H 0.200817 0.659911 0.416591 0.067 Uiso 1 1 calc R U . . .
C10 C 0.1478(2) 0.5928(4) 0.27968(18) 0.0685(7) Uani 1 1 d . . . . .
H10 H 0.161992 0.726006 0.254872 0.082 Uiso 1 1 calc R U . . .
C11 C 0.1034(2) 0.4357(5) 0.22042(17) 0.0701(7) Uani 1 1 d . . . . .
H11 H 0.086542 0.463016 0.155658 0.084 Uiso 1 1 calc R U . . .
C12 C 0.08403(19) 0.2383(4) 0.25710(16) 0.0655(7) Uani 1 1 d . . . . .
H12 H 0.054341 0.131534 0.217044 0.079 Uiso 1 1 calc R U . . .
C13 C 0.10849(16) 0.1979(4) 0.35320(15) 0.0516(6) Uani 1 1 d . . . . .
H13 H 0.095712 0.063209 0.377197 0.062 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
F1 C1 1.398(2) . ?
O1 H1 0.8200 . ?
O1 C7 1.241(2) . ?
O2 C7 1.261(2) . ?
C1 C2 1.542(3) . ?
C1 C5 1.538(3) . ?
C1 C7 1.515(3) . ?
C2 C3 1.561(3) . ?
C2 C6 1.557(3) . ?
C2 C8 1.494(3) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 C4 1.538(3) . ?
C4 H4 0.9800 . ?
C4 C5 1.525(3) . ?
C4 C6 1.534(3) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C8 C9 1.381(3) . ?
C8 C13 1.388(3) . ?
C9 H9 0.9300 . ?
C9 C10 1.390(3) . ?
C10 H10 0.9300 . ?
C10 C11 1.374(4) . ?
C11 H11 0.9300 . ?
C11 C12 1.373(3) . ?
C12 H12 0.9300 . ?
C12 C13 1.379(3) . ?
C13 H13 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7 O1 H1 109.5 . . ?
F1 C1 C2 109.22(15) . . ?
F1 C1 C5 110.32(17) . . ?
F1 C1 C7 106.41(16) . . ?
C5 C1 C2 100.22(16) . . ?
C7 C1 C2 115.17(17) . . ?
C7 C1 C5 115.39(17) . . ?
C1 C2 C3 99.50(16) . . ?
C1 C2 C6 101.66(16) . . ?
C6 C2 C3 84.87(15) . . ?
C8 C2 C1 118.42(16) . . ?
C8 C2 C3 121.58(16) . . ?
C8 C2 C6 123.87(18) . . ?
C2 C3 H3A 114.8 . . ?
C2 C3 H3B 114.8 . . ?
H3A C3 H3B 111.9 . . ?
C4 C3 C2 82.92(15) . . ?
C4 C3 H3A 114.8 . . ?
C4 C3 H3B 114.8 . . ?
C3 C4 H4 119.9 . . ?
C5 C4 C3 102.53(19) . . ?
C5 C4 H4 119.9 . . ?
C5 C4 C6 102.03(17) . . ?
C6 C4 C3 86.42(17) . . ?
C6 C4 H4 119.9 . . ?
C1 C5 H5A 112.0 . . ?
C1 C5 H5B 112.0 . . ?
C4 C5 C1 99.00(17) . . ?
C4 C5 H5A 112.0 . . ?
C4 C5 H5B 112.0 . . ?
H5A C5 H5B 109.7 . . ?
C2 C6 H6A 114.8 . . ?
C2 C6 H6B 114.8 . . ?
C4 C6 C2 83.16(16) . . ?
C4 C6 H6A 114.8 . . ?
C4 C6 H6B 114.8 . . ?
H6A C6 H6B 111.9 . . ?
O1 C7 O2 124.4(2) . . ?
O1 C7 C1 118.43(19) . . ?
O2 C7 C1 117.21(18) . . ?
C9 C8 C2 121.82(18) . . ?
C9 C8 C13 118.16(19) . . ?
C13 C8 C2 120.02(18) . . ?
C8 C9 H9 119.6 . . ?
C8 C9 C10 120.8(2) . . ?
C10 C9 H9 119.6 . . ?
C9 C10 H10 120.0 . . ?
C11 C10 C9 120.0(2) . . ?
C11 C10 H10 120.0 . . ?
C10 C11 H11 120.1 . . ?
C12 C11 C10 119.8(2) . . ?
C12 C11 H11 120.1 . . ?
C11 C12 H12 119.9 . . ?
C11 C12 C13 120.2(2) . . ?
C13 C12 H12 119.9 . . ?
C8 C13 H13 119.5 . . ?
C12 C13 C8 121.1(2) . . ?
C12 C13 H13 119.5 . . ?

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
F1 C1 C2 C3 70.04(18) . . . . ?
F1 C1 C2 C6 156.71(16) . . . . ?
F1 C1 C2 C8 -63.9(2) . . . . ?
F1 C1 C5 C4 -112.45(19) . . . . ?
F1 C1 C7 O1 9.4(3) . . . . ?
F1 C1 C7 O2 -171.13(17) . . . . ?
C1 C2 C3 C4 66.41(17) . . . . ?
C1 C2 C6 C4 -64.02(16) . . . . ?
C1 C2 C8 C9 -92.8(2) . . . . ?
C1 C2 C8 C13 87.9(2) . . . . ?
C2 C1 C5 C4 2.6(2) . . . . ?
C2 C1 C7 O1 -111.8(2) . . . . ?
C2 C1 C7 O2 67.7(2) . . . . ?
C2 C3 C4 C5 -66.47(18) . . . . ?
C2 C3 C4 C6 35.07(15) . . . . ?
C2 C8 C9 C10 -179.0(2) . . . . ?
C2 C8 C13 C12 178.37(19) . . . . ?
C3 C2 C6 C4 34.65(15) . . . . ?
C3 C2 C8 C9 143.6(2) . . . . ?
C3 C2 C8 C13 -35.7(3) . . . . ?
C3 C4 C5 C1 42.5(2) . . . . ?
C3 C4 C6 C2 -35.16(15) . . . . ?
C5 C1 C2 C3 -45.85(19) . . . . ?
C5 C1 C2 C6 40.83(19) . . . . ?
C5 C1 C2 C8 -179.82(17) . . . . ?
C5 C1 C7 O1 132.1(2) . . . . ?
C5 C1 C7 O2 -48.4(3) . . . . ?
C5 C4 C6 C2 66.90(17) . . . . ?
C6 C2 C3 C4 -34.58(16) . . . . ?
C6 C2 C8 C9 37.0(3) . . . . ?
C6 C2 C8 C13 -142.3(2) . . . . ?
C6 C4 C5 C1 -46.5(2) . . . . ?
C7 C1 C2 C3 -170.33(17) . . . . ?
C7 C1 C2 C6 -83.7(2) . . . . ?
C7 C1 C2 C8 55.7(2) . . . . ?
C7 C1 C5 C4 126.9(2) . . . . ?
C8 C2 C3 C4 -161.6(2) . . . . ?
C8 C2 C6 C4 159.61(18) . . . . ?
C8 C9 C10 C11 0.6(4) . . . . ?
C9 C8 C13 C12 -1.0(3) . . . . ?
C9 C10 C11 C12 -1.0(4) . . . . ?
C10 C11 C12 C13 0.3(4) . . . . ?
C11 C12 C13 C8 0.6(4) . . . . ?
C13 C8 C9 C10 0.3(3) . . . . ?

_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_v109
_audit_block_doi                 10.5517/ccdc.csd.cc2gr9vd
_database_code_depnum_ccdc_archive 'CCDC 2286524'
loop_
_citation_id
_citation_doi
_citation_year
1 10.26434/chemrxiv-2023-78z7p 2023
loop_
_audit_author_name
_audit_author_address
'Iryna Sadkova'
;Enamine Ltd
Ukraine
;
_audit_update_record             
;
2023-08-03 deposited with the CCDC.	2023-10-27 downloaded from the CCDC.
;
_audit_creation_date             2023-03-08
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H13 F3 O2'
_chemical_formula_sum            'C14 H13 F3 O2'
_chemical_formula_weight         270.24
_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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   7.9641(4)
_cell_length_b                   20.6944(9)
_cell_length_c                   8.0024(4)
_cell_angle_alpha                90
_cell_angle_beta                 104.190(3)
_cell_angle_gamma                90
_cell_volume                     1278.65(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3974
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      21.82
_cell_measurement_theta_min      2.64
_shelx_estimated_absorpt_T_max   0.981
_shelx_estimated_absorpt_T_min   0.973
_exptl_absorpt_coefficient_mu    0.122
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.404
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0411
_diffrn_reflns_av_unetI/netI     0.0254
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            17996
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         1.968
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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                1849
_reflns_number_total             2257
_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 2016/6 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.431
_refine_diff_density_min         -0.388
_refine_diff_density_rms         0.046
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     176
_refine_ls_number_reflns         2257
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0684
_refine_ls_R_factor_gt           0.0560
_refine_ls_restrained_S_all      1.036
_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)+(0.0563P)²+1.2150P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1342
_refine_ls_wR_factor_ref         0.1424
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1), C3(H3)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C4(H4A,H4B), C5(H5A,H5B)
2.c Aromatic/amide H refined with riding coordinates:
 C9(H9), C11(H11), C12(H12), C13(H13)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.8672(2) 0.34720(14) 0.7404(3) 0.1083(10) Uani 1 1 d . . . . .
F2 F 0.8060(3) 0.25154(11) 0.7922(4) 0.1182(10) Uani 1 1 d . . . . .
F3 F 0.7700(3) 0.32647(13) 0.9545(2) 0.0940(8) Uani 1 1 d . . . . .
O1 O 0.0186(2) 0.48671(9) 0.3007(2) 0.0443(5) Uani 1 1 d . . . . .
O2 O 0.2293(2) 0.50262(9) 0.5382(2) 0.0404(5) Uani 1 1 d . . . . .
H2 H 0.139(5) 0.5068(18) 0.593(5) 0.093(12) Uiso 1 1 d . . . . .
C1 C 0.3150(3) 0.47543(11) 0.2858(3) 0.0320(5) Uani 1 1 d . . . . .
H1 H 0.426402 0.495041 0.351671 0.038 Uiso 1 1 calc R U . . .
C2 C 0.2793(3) 0.49481(12) 0.0924(3) 0.0405(6) Uani 1 1 d . . . . .
H2A H 0.160484 0.511806 0.048240 0.049 Uiso 1 1 calc R U . . .
H2B H 0.364288 0.526875 0.071849 0.049 Uiso 1 1 calc R U . . .
C3 C 0.3027(3) 0.42904(13) 0.0146(3) 0.0458(7) Uani 1 1 d . . . . .
H3 H 0.292692 0.425077 -0.112064 0.055 Uiso 1 1 calc R U . . .
C4 C 0.4641(3) 0.40092(14) 0.1456(3) 0.0420(6) Uani 1 1 d . . . . .
H4A H 0.501050 0.357646 0.115739 0.050 Uiso 1 1 calc R U . . .
H4B H 0.563025 0.431077 0.179966 0.050 Uiso 1 1 calc R U . . .
C5 C 0.1927(3) 0.38464(13) 0.1030(3) 0.0436(6) Uani 1 1 d . . . . .
H5A H 0.187294 0.338820 0.066565 0.052 Uiso 1 1 calc R U . . .
H5B H 0.076926 0.401853 0.103878 0.052 Uiso 1 1 calc R U . . .
C6 C 0.3381(3) 0.40053(11) 0.2668(3) 0.0325(5) Uani 1 1 d . . . . .
C7 C 0.1740(3) 0.48965(10) 0.3747(3) 0.0299(5) Uani 1 1 d . . . . .
C8 C 0.3713(3) 0.36209(11) 0.4304(3) 0.0306(5) Uani 1 1 d . . . . .
C9 C 0.5397(3) 0.35441(11) 0.5299(3) 0.0320(5) Uani 1 1 d . . . . .
H9 H 0.633708 0.372574 0.492256 0.038 Uiso 1 1 calc R U . . .
C10 C 0.5713(3) 0.32023(11) 0.6843(3) 0.0351(6) Uani 1 1 d . . . . .
C11 C 0.4352(3) 0.29361(12) 0.7409(3) 0.0405(6) Uani 1 1 d . . . . .
H11 H 0.456776 0.270522 0.846639 0.049 Uiso 1 1 calc R U . . .
C12 C 0.2678(3) 0.30103(12) 0.6418(3) 0.0435(6) Uani 1 1 d . . . . .
H12 H 0.173995 0.282966 0.679843 0.052 Uiso 1 1 calc R U . . .
C13 C 0.2357(3) 0.33471(11) 0.4869(3) 0.0372(6) Uani 1 1 d . . . . .
H13 H 0.120283 0.339043 0.419130 0.045 Uiso 1 1 calc R U . . .
C14 C 0.7513(4) 0.31148(14) 0.7907(3) 0.0470(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
F1 C14 1.321(3) . ?
F2 C14 1.314(3) . ?
F3 C14 1.319(3) . ?
O1 C7 1.235(3) . ?
O2 H2 0.94(4) . ?
O2 C7 1.302(3) . ?
C1 H1 1.0000 . ?
C1 C2 1.556(3) . ?
C1 C6 1.573(3) . ?
C1 C7 1.498(3) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C3 1.527(4) . ?
C3 H3 1.0000 . ?
C3 C4 1.558(4) . ?
C3 C5 1.555(4) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C6 1.557(3) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5 C6 1.556(3) . ?
C6 C8 1.499(3) . ?
C8 C9 1.391(3) . ?
C8 C13 1.389(3) . ?
C9 H9 0.9500 . ?
C9 C10 1.392(3) . ?
C10 C11 1.388(3) . ?
C10 C14 1.488(4) . ?
C11 H11 0.9500 . ?
C11 C12 1.382(4) . ?
C12 H12 0.9500 . ?
C12 C13 1.390(4) . ?
C13 H13 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7 O2 H2 112(2) . . ?
C2 C1 H1 110.0 . . ?
C2 C1 C6 98.90(18) . . ?
C6 C1 H1 110.0 . . ?
C7 C1 H1 110.0 . . ?
C7 C1 C2 116.48(19) . . ?
C7 C1 C6 111.01(18) . . ?
C1 C2 H2A 111.9 . . ?
C1 C2 H2B 111.9 . . ?
H2A C2 H2B 109.6 . . ?
C3 C2 C1 99.51(19) . . ?
C3 C2 H2A 111.9 . . ?
C3 C2 H2B 111.9 . . ?
C2 C3 H3 119.9 . . ?
C2 C3 C4 102.8(2) . . ?
C2 C3 C5 101.6(2) . . ?
C4 C3 H3 119.9 . . ?
C5 C3 H3 119.9 . . ?
C5 C3 C4 86.37(19) . . ?
C3 C4 H4A 114.9 . . ?
C3 C4 H4B 114.9 . . ?
H4A C4 H4B 111.9 . . ?
C6 C4 C3 82.54(17) . . ?
C6 C4 H4A 114.9 . . ?
C6 C4 H4B 114.9 . . ?
C3 C5 H5A 114.9 . . ?
C3 C5 H5B 114.9 . . ?
C3 C5 C6 82.68(18) . . ?
H5A C5 H5B 111.9 . . ?
C6 C5 H5A 114.9 . . ?
C6 C5 H5B 114.9 . . ?
C4 C6 C1 99.42(19) . . ?
C5 C6 C1 102.09(18) . . ?
C5 C6 C4 86.37(18) . . ?
C8 C6 C1 115.97(18) . . ?
C8 C6 C4 122.96(19) . . ?
C8 C6 C5 124.0(2) . . ?
O1 C7 O2 123.0(2) . . ?
O1 C7 C1 122.8(2) . . ?
O2 C7 C1 114.13(19) . . ?
C9 C8 C6 120.0(2) . . ?
C13 C8 C6 121.0(2) . . ?
C13 C8 C9 119.0(2) . . ?
C8 C9 H9 119.8 . . ?
C8 C9 C10 120.3(2) . . ?
C10 C9 H9 119.8 . . ?
C9 C10 C14 120.6(2) . . ?
C11 C10 C9 120.4(2) . . ?
C11 C10 C14 119.0(2) . . ?
C10 C11 H11 120.4 . . ?
C12 C11 C10 119.3(2) . . ?
C12 C11 H11 120.4 . . ?
C11 C12 H12 119.7 . . ?
C11 C12 C13 120.5(2) . . ?
C13 C12 H12 119.7 . . ?
C8 C13 C12 120.4(2) . . ?
C8 C13 H13 119.8 . . ?
C12 C13 H13 119.8 . . ?
F1 C14 C10 113.9(2) . . ?
F2 C14 F1 106.0(3) . . ?
F2 C14 F3 104.9(2) . . ?
F2 C14 C10 113.0(2) . . ?
F3 C14 F1 104.7(3) . . ?
F3 C14 C10 113.5(2) . . ?

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 -41.4(2) . . . . ?
C1 C2 C3 C5 47.5(2) . . . . ?
C1 C6 C8 C9 -86.9(3) . . . . ?
C1 C6 C8 C13 91.9(3) . . . . ?
C2 C1 C6 C4 47.6(2) . . . . ?
C2 C1 C6 C5 -40.7(2) . . . . ?
C2 C1 C6 C8 -178.47(19) . . . . ?
C2 C1 C7 O1 34.1(3) . . . . ?
C2 C1 C7 O2 -148.7(2) . . . . ?
C2 C3 C4 C6 66.7(2) . . . . ?
C2 C3 C5 C6 -67.9(2) . . . . ?
C3 C4 C6 C1 -67.26(19) . . . . ?
C3 C4 C6 C5 34.41(18) . . . . ?
C3 C4 C6 C8 163.2(2) . . . . ?
C3 C5 C6 C1 64.39(19) . . . . ?
C3 C5 C6 C4 -34.48(18) . . . . ?
C3 C5 C6 C8 -162.4(2) . . . . ?
C4 C3 C5 C6 34.45(17) . . . . ?
C4 C6 C8 C9 35.3(3) . . . . ?
C4 C6 C8 C13 -145.9(2) . . . . ?
C5 C3 C4 C6 -34.44(18) . . . . ?
C5 C6 C8 C9 145.6(2) . . . . ?
C5 C6 C8 C13 -35.6(3) . . . . ?
C6 C1 C2 C3 -3.7(2) . . . . ?
C6 C1 C7 O1 -78.0(3) . . . . ?
C6 C1 C7 O2 99.1(2) . . . . ?
C6 C8 C9 C10 178.3(2) . . . . ?
C6 C8 C13 C12 -177.8(2) . . . . ?
C7 C1 C2 C3 -122.6(2) . . . . ?
C7 C1 C6 C4 170.49(18) . . . . ?
C7 C1 C6 C5 82.2(2) . . . . ?
C7 C1 C6 C8 -55.5(3) . . . . ?
C8 C9 C10 C11 -0.2(3) . . . . ?
C8 C9 C10 C14 179.6(2) . . . . ?
C9 C8 C13 C12 1.0(3) . . . . ?
C9 C10 C11 C12 0.4(4) . . . . ?
C9 C10 C14 F1 10.6(4) . . . . ?
C9 C10 C14 F2 -110.4(3) . . . . ?
C9 C10 C14 F3 130.3(3) . . . . ?
C10 C11 C12 C13 0.1(4) . . . . ?
C11 C10 C14 F1 -169.6(3) . . . . ?
C11 C10 C14 F2 69.4(3) . . . . ?
C11 C10 C14 F3 -49.9(3) . . . . ?
C11 C12 C13 C8 -0.8(4) . . . . ?
C13 C8 C9 C10 -0.5(3) . . . . ?
C14 C10 C11 C12 -179.4(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_v123
_audit_block_doi                 10.5517/ccdc.csd.cc2gr9tc
_database_code_depnum_ccdc_archive 'CCDC 2286523'
loop_
_citation_id
_citation_doi
_citation_year
1 10.26434/chemrxiv-2023-78z7p 2023
loop_
_audit_author_name
_audit_author_address
'Iryna Sadkova'
;Enamine Ltd
Ukraine
;
_audit_update_record             
;
2023-08-03 deposited with the CCDC.	2023-10-27 downloaded from the CCDC.
;
_audit_creation_date             2023-03-21
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '0.5(C18 H16 Cl2 N2 O), 0.5(H2 O)'
_chemical_formula_sum            'C9 H9 Cl N O'
_chemical_formula_weight         182.62
_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'
Cl Cl 0.1484 0.1585 '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                   18.3768(13)
_cell_length_b                   6.9898(4)
_cell_length_c                   27.6891(17)
_cell_angle_alpha                90
_cell_angle_beta                 103.554(7)
_cell_angle_gamma                90
_cell_volume                     3457.6(4)
_cell_formula_units_Z            16
_cell_measurement_reflns_used    9067
_cell_measurement_temperature    273.15
_cell_measurement_theta_max      30.55
_cell_measurement_theta_min      2.28
_shelx_estimated_absorpt_T_max   0.955
_shelx_estimated_absorpt_T_min   0.926
_exptl_absorpt_coefficient_mu    0.388
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.403
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1520
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0833
_diffrn_reflns_av_unetI/netI     0.0575
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_number            29127
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.999
_diffrn_reflns_theta_min         2.280
_diffrn_ambient_temperature      273.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_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                3730
_reflns_number_total             5031
_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 2016/6 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.553
_refine_diff_density_min         -0.416
_refine_diff_density_rms         0.073
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.106
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     224
_refine_ls_number_reflns         5031
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1055
_refine_ls_R_factor_gt           0.0719
_refine_ls_restrained_S_all      1.106
_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)+(0.0300P)²+11.7087P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1328
_refine_ls_wR_factor_ref         0.1447
_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,H) groups
2.a Free rotating group:
 O1W(H1WA,H1WB)
2.b Ternary CH refined with riding coordinates:
 C4(H4), C6(H6)
2.c Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B), C5(H5A,H5B)
2.d Aromatic/amide H refined with riding coordinates:
 C9(H9), C10(H10), C11(H11), C14(H14), C15(H15), C17(H17), C18(H18)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.57711(13) 0.1180(3) 0.65634(9) 0.0207(5) Uani 1 1 d . . . . .
C2 C 0.52842(14) -0.0579(4) 0.63455(10) 0.0261(5) Uani 1 1 d . . . . .
H2A H 0.522086 -0.076482 0.599096 0.031 Uiso 1 1 calc R U . . .
H2B H 0.541455 -0.175984 0.652932 0.031 Uiso 1 1 calc R U . . .
C3 C 0.52699(16) 0.1305(4) 0.69451(10) 0.0295(6) Uani 1 1 d . . . . .
H3A H 0.539819 0.040737 0.721918 0.035 Uiso 1 1 calc R U . . .
H3B H 0.519490 0.258799 0.705756 0.035 Uiso 1 1 calc R U . . .
C4 C 0.46556(15) 0.0598(4) 0.64943(10) 0.0283(6) Uani 1 1 d . . . . .
H4 H 0.420753 -0.004598 0.654819 0.034 Uiso 1 1 calc R U . . .
C5 C 0.45794(14) 0.2288(4) 0.61351(11) 0.0291(6) Uani 1 1 d . . . . .
H5A H 0.429347 0.332805 0.623105 0.035 Uiso 1 1 calc R U . . .
H5B H 0.435587 0.191019 0.579558 0.035 Uiso 1 1 calc R U . . .
C6 C 0.54216(13) 0.2810(4) 0.62091(9) 0.0212(5) Uani 1 1 d . . . . .
H6 H 0.552016 0.403880 0.638276 0.025 Uiso 1 1 calc R U . . .
C7 C 0.59735(13) 0.4476(3) 0.56121(9) 0.0194(5) Uani 1 1 d . . . . .
C8 C 0.63485(13) 0.4275(3) 0.51849(9) 0.0187(4) Uani 1 1 d . . . . .
C9 C 0.59754(14) 0.3487(4) 0.47342(9) 0.0240(5) Uani 1 1 d . . . . .
H9 H 0.549089 0.302040 0.469357 0.029 Uiso 1 1 calc R U . . .
C10 C 0.63319(16) 0.3403(4) 0.43453(10) 0.0289(6) Uani 1 1 d . . . . .
H10 H 0.609010 0.289490 0.403942 0.035 Uiso 1 1 calc R U . . .
C11 C 0.70524(16) 0.4091(4) 0.44226(10) 0.0303(6) Uani 1 1 d . . . . .
H11 H 0.728929 0.403441 0.416072 0.036 Uiso 1 1 calc R U . . .
C12 C 0.70773(13) 0.4918(3) 0.52202(9) 0.0194(5) Uani 1 1 d . . . . .
C13 C 0.66098(14) 0.1132(4) 0.67181(9) 0.0231(5) Uani 1 1 d . . . . .
C14 C 0.70001(16) 0.2734(4) 0.69291(11) 0.0354(7) Uani 1 1 d . . . . .
H14 H 0.673709 0.383085 0.697372 0.042 Uiso 1 1 calc R U . . .
C15 C 0.77794(17) 0.2739(5) 0.70762(12) 0.0403(7) Uani 1 1 d . . . . .
H15 H 0.803741 0.382387 0.721667 0.048 Uiso 1 1 calc R U . . .
C16 C 0.81559(15) 0.1106(5) 0.70086(10) 0.0318(6) Uani 1 1 d . . . . .
C17 C 0.77892(16) -0.0512(4) 0.68000(10) 0.0326(6) Uani 1 1 d . . . . .
H17 H 0.805632 -0.160432 0.675711 0.039 Uiso 1 1 calc R U . . .
C18 C 0.70086(15) -0.0493(4) 0.66531(10) 0.0268(5) Uani 1 1 d . . . . .
H18 H 0.675414 -0.157914 0.651039 0.032 Uiso 1 1 calc R U . . .
Cl1 Cl 0.76022(4) 0.58193(10) 0.57790(3) 0.03066(16) Uani 1 1 d . . . . .
Cl2 Cl 0.91341(4) 0.11088(14) 0.71861(3) 0.0506(2) Uani 1 1 d . . . . .
N1 N 0.57131(11) 0.2857(3) 0.57617(8) 0.0196(4) Uani 1 1 d . . . . .
N2 N 0.74322(12) 0.4838(3) 0.48564(8) 0.0251(5) Uani 1 1 d . . . . .
O1 O 0.59171(11) 0.6059(3) 0.57937(8) 0.0306(4) Uani 1 1 d . . . . .
O1W O 0.60658(11) 0.9444(3) 0.52766(8) 0.0308(4) Uani 1 1 d G . . . .
H1WA H 0.605901 0.839546 0.543119 0.046 Uiso 1 1 d G U . . .
H1WB H 0.647604 0.941717 0.518481 0.046 Uiso 1 1 d G U . . .
H1 H 0.5822(15) 0.177(4) 0.5641(10) 0.017(7) 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 C2 1.556(4) . ?
C1 C3 1.559(3) . ?
C1 C6 1.542(3) . ?
C1 C13 1.500(3) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 C4 1.550(4) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 C4 1.554(4) . ?
C4 H4 0.9800 . ?
C4 C5 1.529(4) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C5 C6 1.556(3) . ?
C6 H6 0.9800 . ?
C6 N1 1.461(3) . ?
C7 C8 1.509(3) . ?
C7 N1 1.332(3) . ?
C7 O1 1.229(3) . ?
C8 C9 1.389(3) . ?
C8 C12 1.394(3) . ?
C9 H9 0.9300 . ?
C9 C10 1.386(4) . ?
C10 H10 0.9300 . ?
C10 C11 1.377(4) . ?
C11 H11 0.9300 . ?
C11 N2 1.345(4) . ?
C12 Cl1 1.738(3) . ?
C12 N2 1.323(3) . ?
C13 C14 1.383(4) . ?
C13 C18 1.386(4) . ?
C14 H14 0.9300 . ?
C14 C15 1.394(4) . ?
C15 H15 0.9300 . ?
C15 C16 1.370(4) . ?
C16 C17 1.373(4) . ?
C16 Cl2 1.749(3) . ?
C17 H17 0.9300 . ?
C17 C18 1.396(4) . ?
C18 H18 0.9300 . ?
N1 H1 0.87(3) . ?
O1W H1WA 0.8502 . ?
O1W H1WB 0.8505 . ?

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 C3 85.97(19) . . ?
C6 C1 C2 102.8(2) . . ?
C6 C1 C3 99.55(19) . . ?
C13 C1 C2 123.5(2) . . ?
C13 C1 C3 122.6(2) . . ?
C13 C1 C6 116.4(2) . . ?
C1 C2 H2A 114.8 . . ?
C1 C2 H2B 114.8 . . ?
H2A C2 H2B 111.9 . . ?
C4 C2 C1 82.79(18) . . ?
C4 C2 H2A 114.8 . . ?
C4 C2 H2B 114.8 . . ?
C1 C3 H3A 114.9 . . ?
C1 C3 H3B 114.9 . . ?
H3A C3 H3B 111.9 . . ?
C4 C3 C1 82.59(18) . . ?
C4 C3 H3A 114.9 . . ?
C4 C3 H3B 114.9 . . ?
C2 C4 C3 86.3(2) . . ?
C2 C4 H4 120.1 . . ?
C3 C4 H4 120.1 . . ?
C5 C4 C2 101.4(2) . . ?
C5 C4 C3 102.4(2) . . ?
C5 C4 H4 120.1 . . ?
C4 C5 H5A 111.9 . . ?
C4 C5 H5B 111.9 . . ?
C4 C5 C6 99.1(2) . . ?
H5A C5 H5B 109.6 . . ?
C6 C5 H5A 111.9 . . ?
C6 C5 H5B 111.9 . . ?
C1 C6 C5 99.40(19) . . ?
C1 C6 H6 109.5 . . ?
C5 C6 H6 109.5 . . ?
N1 C6 C1 112.04(19) . . ?
N1 C6 C5 116.4(2) . . ?
N1 C6 H6 109.5 . . ?
N1 C7 C8 115.3(2) . . ?
O1 C7 C8 120.2(2) . . ?
O1 C7 N1 124.5(2) . . ?
C9 C8 C7 121.4(2) . . ?
C9 C8 C12 117.0(2) . . ?
C12 C8 C7 121.5(2) . . ?
C8 C9 H9 120.3 . . ?
C10 C9 C8 119.4(2) . . ?
C10 C9 H9 120.3 . . ?
C9 C10 H10 120.8 . . ?
C11 C10 C9 118.5(2) . . ?
C11 C10 H10 120.8 . . ?
C10 C11 H11 118.2 . . ?
N2 C11 C10 123.6(2) . . ?
N2 C11 H11 118.2 . . ?
C8 C12 Cl1 120.18(18) . . ?
N2 C12 C8 124.7(2) . . ?
N2 C12 Cl1 115.03(18) . . ?
C14 C13 C1 119.9(2) . . ?
C14 C13 C18 118.7(2) . . ?
C18 C13 C1 121.4(2) . . ?
C13 C14 H14 119.3 . . ?
C13 C14 C15 121.4(3) . . ?
C15 C14 H14 119.3 . . ?
C14 C15 H15 120.8 . . ?
C16 C15 C14 118.4(3) . . ?
C16 C15 H15 120.8 . . ?
C15 C16 C17 122.0(3) . . ?
C15 C16 Cl2 118.6(2) . . ?
C17 C16 Cl2 119.4(2) . . ?
C16 C17 H17 120.5 . . ?
C16 C17 C18 118.9(3) . . ?
C18 C17 H17 120.5 . . ?
C13 C18 C17 120.6(3) . . ?
C13 C18 H18 119.7 . . ?
C17 C18 H18 119.7 . . ?
C6 N1 H1 118.0(18) . . ?
C7 N1 C6 120.8(2) . . ?
C7 N1 H1 119.2(18) . . ?
C12 N2 C11 116.8(2) . . ?
H1WA O1W H1WB 104.5 . . ?

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
C1 C2 C4 C3 -34.73(18) . . . . ?
C1 C2 C4 C5 67.2(2) . . . . ?
C1 C3 C4 C2 34.69(18) . . . . ?
C1 C3 C4 C5 -66.2(2) . . . . ?
C1 C6 N1 C7 -129.6(2) . . . . ?
C1 C13 C14 C15 -179.9(3) . . . . ?
C1 C13 C18 C17 -179.9(2) . . . . ?
C2 C1 C3 C4 -34.56(18) . . . . ?
C2 C1 C6 C5 40.1(2) . . . . ?
C2 C1 C6 N1 -83.5(2) . . . . ?
C2 C1 C13 C14 -177.1(2) . . . . ?
C2 C1 C13 C18 3.1(4) . . . . ?
C2 C4 C5 C6 -47.7(2) . . . . ?
C3 C1 C2 C4 34.64(19) . . . . ?
C3 C1 C6 C5 -47.9(2) . . . . ?
C3 C1 C6 N1 -171.5(2) . . . . ?
C3 C1 C13 C14 -68.3(3) . . . . ?
C3 C1 C13 C18 111.9(3) . . . . ?
C3 C4 C5 C6 41.0(2) . . . . ?
C4 C5 C6 C1 4.2(2) . . . . ?
C4 C5 C6 N1 124.6(2) . . . . ?
C5 C6 N1 C7 117.0(3) . . . . ?
C6 C1 C2 C4 -64.2(2) . . . . ?
C6 C1 C3 C4 67.7(2) . . . . ?
C6 C1 C13 C14 54.2(3) . . . . ?
C6 C1 C13 C18 -125.6(3) . . . . ?
C7 C8 C9 C10 177.3(2) . . . . ?
C7 C8 C12 Cl1 4.8(3) . . . . ?
C7 C8 C12 N2 -177.9(2) . . . . ?
C8 C7 N1 C6 172.4(2) . . . . ?
C8 C9 C10 C11 0.7(4) . . . . ?
C8 C12 N2 C11 0.5(4) . . . . ?
C9 C8 C12 Cl1 -176.94(18) . . . . ?
C9 C8 C12 N2 0.4(4) . . . . ?
C9 C10 C11 N2 0.1(4) . . . . ?
C10 C11 N2 C12 -0.7(4) . . . . ?
C12 C8 C9 C10 -1.0(4) . . . . ?
C13 C1 C2 C4 161.6(2) . . . . ?
C13 C1 C3 C4 -162.3(2) . . . . ?
C13 C1 C6 C5 178.2(2) . . . . ?
C13 C1 C6 N1 54.6(3) . . . . ?
C13 C14 C15 C16 -0.2(5) . . . . ?
C14 C13 C18 C17 0.3(4) . . . . ?
C14 C15 C16 C17 0.3(5) . . . . ?
C14 C15 C16 Cl2 179.3(2) . . . . ?
C15 C16 C17 C18 -0.1(4) . . . . ?
C16 C17 C18 C13 -0.2(4) . . . . ?
C18 C13 C14 C15 -0.1(4) . . . . ?
Cl1 C12 N2 C11 177.89(19) . . . . ?
Cl2 C16 C17 C18 -179.1(2) . . . . ?
N1 C7 C8 C9 57.2(3) . . . . ?
N1 C7 C8 C12 -124.6(2) . . . . ?
O1 C7 C8 C9 -122.0(3) . . . . ?
O1 C7 C8 C12 56.2(3) . . . . ?
O1 C7 N1 C6 -8.5(4) . . . . ?

_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_vd29
_audit_block_doi                 10.5517/ccdc.csd.cc2gr9wf
_database_code_depnum_ccdc_archive 'CCDC 2286525'
loop_
_citation_id
_citation_doi
_citation_year
1 10.26434/chemrxiv-2023-78z7p 2023
loop_
_audit_author_name
_audit_author_address
'Iryna Sadkova'
;Enamine Ltd
Ukraine
;
_audit_update_record             
;
2023-08-03 deposited with the CCDC.	2023-10-27 downloaded from the CCDC.
;
_audit_creation_date             2022-09-02
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H15 F O3'
_chemical_formula_sum            'C14 H15 F O3'
_chemical_formula_weight         250.26
_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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   9.5011(14)
_cell_length_b                   11.9938(15)
_cell_length_c                   11.5637(17)
_cell_angle_alpha                90
_cell_angle_beta                 109.290(7)
_cell_angle_gamma                90
_cell_volume                     1243.8(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3219
_cell_measurement_temperature    273.15
_cell_measurement_theta_max      22.30
_cell_measurement_theta_min      2.27
_shelx_estimated_absorpt_T_max   0.983
_shelx_estimated_absorpt_T_min   0.980
_exptl_absorpt_coefficient_mu    0.103
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.336
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.17
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0574
_diffrn_reflns_av_unetI/netI     0.0348
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            15158
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         2.271
_diffrn_ambient_temperature      273.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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                1595
_reflns_number_total             2190
_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 2016/6 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_refine_diff_density_max         0.177
_refine_diff_density_min         -0.235
_refine_diff_density_rms         0.040
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     165
_refine_ls_number_reflns         2190
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0675
_refine_ls_R_factor_gt           0.0473
_refine_ls_restrained_S_all      1.046
_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)+(0.0620P)²+0.3702P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1199
_refine_ls_wR_factor_ref         0.1367
_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 C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C3(H3)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C4(H4A,H4B), C6(H6A,H6B)
2.c Aromatic/amide H refined with riding coordinates:
 C9(H9), C10(H10), C12(H12), C13(H13)
2.d Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C)
2.e Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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
F1 F 0.46053(14) 0.04698(12) 0.83419(11) 0.0634(4) Uani 1 1 d . . . . .
O1 O 0.4502(2) -0.02670(14) 0.62725(14) 0.0654(5) Uani 1 1 d . . . . .
H1 H 0.449998 -0.047600 0.559685 0.098 Uiso 1 1 calc R U . . .
O2 O 0.6091(2) 0.09702(14) 0.60013(14) 0.0720(5) Uani 1 1 d . . . . .
O3 O 0.8554(2) -0.40757(13) 0.91978(15) 0.0708(5) Uani 1 1 d . . . . .
C1 C 0.7265(2) 0.05469(18) 0.88276(18) 0.0493(5) Uani 1 1 d . . . . .
C2 C 0.7305(3) 0.1262(2) 0.9976(2) 0.0637(7) Uani 1 1 d . . . . .
H2A H 0.640398 0.122904 1.019341 0.076 Uiso 1 1 calc R U . . .
H2B H 0.819456 0.116518 1.068428 0.076 Uiso 1 1 calc R U . . .
C3 C 0.7371(3) 0.2234(2) 0.9133(2) 0.0664(7) Uani 1 1 d . . . . .
H3 H 0.778013 0.295418 0.948973 0.080 Uiso 1 1 calc R U . . .
C4 C 0.5836(3) 0.21865(19) 0.8140(2) 0.0643(7) Uani 1 1 d . . . . .
H4A H 0.581851 0.258369 0.740484 0.077 Uiso 1 1 calc R U . . .
H4B H 0.505643 0.247046 0.843013 0.077 Uiso 1 1 calc R U . . .
C5 C 0.5721(2) 0.09204(18) 0.79411(18) 0.0497(5) Uani 1 1 d . . . . .
C6 C 0.8300(3) 0.14676(19) 0.8597(2) 0.0609(6) Uani 1 1 d . . . . .
H6A H 0.934248 0.140181 0.909251 0.073 Uiso 1 1 calc R U . . .
H6B H 0.817550 0.160044 0.774112 0.073 Uiso 1 1 calc R U . . .
C7 C 0.5408(2) 0.05120(17) 0.66350(18) 0.0463(5) Uani 1 1 d . . . . .
C8 C 0.7614(2) -0.06690(18) 0.88993(17) 0.0468(5) Uani 1 1 d . . . . .
C9 C 0.8313(3) -0.11655(19) 0.81517(19) 0.0532(6) Uani 1 1 d . . . . .
H9 H 0.857242 -0.072538 0.759122 0.064 Uiso 1 1 calc R U . . .
C10 C 0.8638(3) -0.22904(19) 0.82106(19) 0.0549(6) Uani 1 1 d . . . . .
H10 H 0.910950 -0.259657 0.769657 0.066 Uiso 1 1 calc R U . . .
C11 C 0.8260(2) -0.29615(18) 0.90369(18) 0.0516(6) Uani 1 1 d . . . . .
C12 C 0.7543(2) -0.24847(19) 0.97821(19) 0.0563(6) Uani 1 1 d . . . . .
H12 H 0.727269 -0.292858 1.033384 0.068 Uiso 1 1 calc R U . . .
C13 C 0.7228(3) -0.13643(19) 0.97153(18) 0.0543(6) Uani 1 1 d . . . . .
H13 H 0.674668 -0.106232 1.022476 0.065 Uiso 1 1 calc R U . . .
C14 C 0.9141(4) -0.4629(2) 0.8373(3) 0.0821(8) Uani 1 1 d . . . . .
H14A H 0.848445 -0.451930 0.754868 0.123 Uiso 1 1 calc R U . . .
H14B H 0.922813 -0.541135 0.855627 0.123 Uiso 1 1 calc R U . . .
H14C H 1.010605 -0.432941 0.845533 0.123 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
F1 C5 1.398(2) . ?
O1 H1 0.8200 . ?
O1 C7 1.246(2) . ?
O2 C7 1.254(2) . ?
O3 C11 1.365(3) . ?
O3 C14 1.418(3) . ?
C1 C2 1.570(3) . ?
C1 C5 1.552(3) . ?
C1 C6 1.559(3) . ?
C1 C8 1.492(3) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 C3 1.535(4) . ?
C3 H3 0.9800 . ?
C3 C4 1.531(3) . ?
C3 C6 1.539(3) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 C5 1.534(3) . ?
C5 C7 1.521(3) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C8 C9 1.387(3) . ?
C8 C13 1.396(3) . ?
C9 H9 0.9300 . ?
C9 C10 1.381(3) . ?
C10 H10 0.9300 . ?
C10 C11 1.385(3) . ?
C11 C12 1.386(3) . ?
C12 H12 0.9300 . ?
C12 C13 1.373(3) . ?
C13 H13 0.9300 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7 O1 H1 109.5 . . ?
C11 O3 C14 118.31(19) . . ?
C5 C1 C2 98.90(17) . . ?
C5 C1 C6 101.21(17) . . ?
C6 C1 C2 85.26(16) . . ?
C8 C1 C2 122.95(18) . . ?
C8 C1 C5 117.57(17) . . ?
C8 C1 C6 124.12(18) . . ?
C1 C2 H2A 114.9 . . ?
C1 C2 H2B 114.9 . . ?
H2A C2 H2B 111.9 . . ?
C3 C2 C1 82.69(16) . . ?
C3 C2 H2A 114.9 . . ?
C3 C2 H2B 114.9 . . ?
C2 C3 H3 119.7 . . ?
C2 C3 C6 87.18(18) . . ?
C4 C3 C2 102.6(2) . . ?
C4 C3 H3 119.7 . . ?
C4 C3 C6 101.92(18) . . ?
C6 C3 H3 119.7 . . ?
C3 C4 H4A 112.0 . . ?
C3 C4 H4B 112.0 . . ?
C3 C4 C5 98.78(18) . . ?
H4A C4 H4B 109.7 . . ?
C5 C4 H4A 112.0 . . ?
C5 C4 H4B 112.0 . . ?
F1 C5 C1 108.91(17) . . ?
F1 C5 C4 110.91(17) . . ?
F1 C5 C7 106.49(16) . . ?
C4 C5 C1 100.47(17) . . ?
C7 C5 C1 113.26(17) . . ?
C7 C5 C4 116.66(18) . . ?
C1 C6 H6A 114.8 . . ?
C1 C6 H6B 114.8 . . ?
C3 C6 C1 82.90(17) . . ?
C3 C6 H6A 114.8 . . ?
C3 C6 H6B 114.8 . . ?
H6A C6 H6B 111.9 . . ?
O1 C7 O2 124.43(19) . . ?
O1 C7 C5 117.53(19) . . ?
O2 C7 C5 118.03(18) . . ?
C9 C8 C1 121.90(18) . . ?
C9 C8 C13 116.9(2) . . ?
C13 C8 C1 121.23(19) . . ?
C8 C9 H9 118.9 . . ?
C10 C9 C8 122.3(2) . . ?
C10 C9 H9 118.9 . . ?
C9 C10 H10 120.1 . . ?
C9 C10 C11 119.8(2) . . ?
C11 C10 H10 120.1 . . ?
O3 C11 C10 125.1(2) . . ?
O3 C11 C12 116.1(2) . . ?
C10 C11 C12 118.8(2) . . ?
C11 C12 H12 119.6 . . ?
C13 C12 C11 120.8(2) . . ?
C13 C12 H12 119.6 . . ?
C8 C13 H13 119.3 . . ?
C12 C13 C8 121.4(2) . . ?
C12 C13 H13 119.3 . . ?
O3 C14 H14A 109.5 . . ?
O3 C14 H14B 109.5 . . ?
O3 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
F1 C5 C7 O1 -14.0(3) . . . . ?
F1 C5 C7 O2 166.90(19) . . . . ?
O3 C11 C12 C13 178.40(19) . . . . ?
C1 C2 C3 C4 67.02(18) . . . . ?
C1 C2 C3 C6 -34.57(16) . . . . ?
C1 C5 C7 O1 105.7(2) . . . . ?
C1 C5 C7 O2 -73.4(3) . . . . ?
C1 C8 C9 C10 -179.9(2) . . . . ?
C1 C8 C13 C12 179.83(19) . . . . ?
C2 C1 C5 F1 -70.63(19) . . . . ?
C2 C1 C5 C4 45.9(2) . . . . ?
C2 C1 C5 C7 171.08(18) . . . . ?
C2 C1 C6 C3 -34.02(17) . . . . ?
C2 C1 C8 C9 -146.1(2) . . . . ?
C2 C1 C8 C13 34.9(3) . . . . ?
C2 C3 C4 C5 -42.9(2) . . . . ?
C2 C3 C6 C1 34.82(16) . . . . ?
C3 C4 C5 F1 112.32(19) . . . . ?
C3 C4 C5 C1 -2.7(2) . . . . ?
C3 C4 C5 C7 -125.5(2) . . . . ?
C4 C3 C6 C1 -67.51(19) . . . . ?
C4 C5 C7 O1 -138.4(2) . . . . ?
C4 C5 C7 O2 42.5(3) . . . . ?
C5 C1 C2 C3 -66.48(18) . . . . ?
C5 C1 C6 C3 64.14(17) . . . . ?
C5 C1 C8 C9 90.8(2) . . . . ?
C5 C1 C8 C13 -88.3(2) . . . . ?
C6 C1 C2 C3 34.15(17) . . . . ?
C6 C1 C5 F1 -157.53(16) . . . . ?
C6 C1 C5 C4 -41.0(2) . . . . ?
C6 C1 C5 C7 84.2(2) . . . . ?
C6 C1 C8 C9 -37.4(3) . . . . ?
C6 C1 C8 C13 143.5(2) . . . . ?
C6 C3 C4 C5 46.8(2) . . . . ?
C8 C1 C2 C3 162.3(2) . . . . ?
C8 C1 C5 F1 64.0(2) . . . . ?
C8 C1 C5 C4 -179.44(18) . . . . ?
C8 C1 C5 C7 -54.3(2) . . . . ?
C8 C1 C6 C3 -161.11(19) . . . . ?
C8 C9 C10 C11 0.1(3) . . . . ?
C9 C8 C13 C12 0.7(3) . . . . ?
C9 C10 C11 O3 -178.4(2) . . . . ?
C9 C10 C11 C12 0.7(3) . . . . ?
C10 C11 C12 C13 -0.8(3) . . . . ?
C11 C12 C13 C8 0.0(3) . . . . ?
C13 C8 C9 C10 -0.8(3) . . . . ?
C14 O3 C11 C10 -7.5(3) . . . . ?
C14 O3 C11 C12 173.4(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_v107
_audit_block_doi                 10.5517/ccdc.csd.cc2gr9yh
_database_code_depnum_ccdc_archive 'CCDC 2286527'
loop_
_citation_id
_citation_doi
_citation_year
1 10.26434/chemrxiv-2023-78z7p 2023
loop_
_audit_author_name
_audit_author_address
'Iryna Sadkova'
;Enamine Ltd
Ukraine
;
_audit_update_record             
;
2023-08-03 deposited with the CCDC.	2023-10-27 downloaded from the CCDC.
;
_audit_creation_date             2023-03-07
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H17 Cl2 F2 N3 O'
_chemical_formula_sum            'C18 H17 Cl2 F2 N3 O'
_chemical_formula_weight         400.24
_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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      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                   10.9193(6)
_cell_length_b                   18.5629(12)
_cell_length_c                   9.7993(5)
_cell_angle_alpha                90
_cell_angle_beta                 115.272(3)
_cell_angle_gamma                90
_cell_volume                     1796.16(18)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5641
_cell_measurement_temperature    273.15
_cell_measurement_theta_max      24.69
_cell_measurement_theta_min      2.19
_shelx_estimated_absorpt_T_max   0.984
_shelx_estimated_absorpt_T_min   0.911
_exptl_absorpt_coefficient_mu    0.394
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.480
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             824
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.04
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0508
_diffrn_reflns_av_unetI/netI     0.0309
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            26745
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        24.998
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_min         2.062
_diffrn_ambient_temperature      273.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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                2531
_reflns_number_total             3158
_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 2016/6 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.260
_refine_diff_density_min         -0.233
_refine_diff_density_rms         0.052
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     240
_refine_ls_number_reflns         3158
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0535
_refine_ls_R_factor_gt           0.0404
_refine_ls_restrained_S_all      1.059
_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)+(0.0482P)²+1.0152P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0969
_refine_ls_wR_factor_ref         0.1041
_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 C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1A), C3(H3), C17(H17)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C4(H4A,H4B), C6(H6A,H6B)
2.c Aromatic/amide H refined with riding coordinates:
 C8(H8), C11(H11), C12(H12), C15(H15)
2.d Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.62468(7) 0.59194(3) 0.48773(7) 0.03961(19) Uani 1 1 d . . . . .
Cl2 Cl 0.89394(6) 0.57636(3) 0.44677(8) 0.0428(2) Uani 1 1 d . . . . .
F1 F 0.94229(17) 0.28680(9) 0.63398(18) 0.0588(5) Uani 1 1 d . . . . .
F2 F 1.01885(17) 0.18708(10) 0.75668(17) 0.0693(6) Uani 1 1 d . . . . .
O1 O 0.61921(15) 0.27065(9) 0.47992(16) 0.0298(4) Uani 1 1 d . . . . .
N1 N 0.53163(18) 0.26086(10) 0.2247(2) 0.0245(4) Uani 1 1 d . . . . .
H1 H 0.545(2) 0.2437(13) 0.154(3) 0.026(7) Uiso 1 1 d . . . . .
N2 N 0.92212(18) 0.12538(11) 0.4873(2) 0.0303(5) Uani 1 1 d . . . . .
N3 N 0.84598(18) 0.10379(10) 0.3432(2) 0.0273(4) Uani 1 1 d . . . . .
C1 C 0.4150(2) 0.30705(12) 0.1939(3) 0.0261(5) Uani 1 1 d . . . . .
H1A H 0.405901 0.316431 0.289615 0.031 Uiso 1 1 calc R U . . .
C2 C 0.2786(2) 0.27743(13) 0.0719(3) 0.0392(6) Uani 1 1 d . . . . .
H2A H 0.291574 0.232434 0.025388 0.047 Uiso 1 1 calc R U . . .
H2B H 0.211340 0.269270 0.113157 0.047 Uiso 1 1 calc R U . . .
C3 C 0.2394(2) 0.34027(14) -0.0381(3) 0.0398(6) Uani 1 1 d . . . . .
H3 H 0.152465 0.338602 -0.131782 0.048 Uiso 1 1 calc R U . . .
C4 C 0.2712(2) 0.40576(13) 0.0683(3) 0.0335(6) Uani 1 1 d . . . . .
H4A H 0.237401 0.402027 0.147046 0.040 Uiso 1 1 calc R U . . .
H4B H 0.249996 0.453132 0.016994 0.040 Uiso 1 1 calc R U . . .
C5 C 0.4197(2) 0.37972(12) 0.1178(2) 0.0263(5) Uani 1 1 d . . . . .
C6 C 0.3734(2) 0.35690(14) -0.0495(3) 0.0373(6) Uani 1 1 d . . . . .
H6A H 0.368197 0.396662 -0.119157 0.045 Uiso 1 1 calc R U . . .
H6B H 0.420636 0.314237 -0.064694 0.045 Uiso 1 1 calc R U . . .
C7 C 0.5389(2) 0.42752(12) 0.1993(2) 0.0258(5) Uani 1 1 d . . . . .
C8 C 0.5308(2) 0.48138(12) 0.2932(2) 0.0268(5) Uani 1 1 d . . . . .
H8 H 0.449010 0.488081 0.303731 0.032 Uiso 1 1 calc R U . . .
C9 C 0.6408(2) 0.52545(12) 0.3716(2) 0.0271(5) Uani 1 1 d . . . . .
C10 C 0.7604(2) 0.51740(12) 0.3568(3) 0.0297(5) Uani 1 1 d . . . . .
C11 C 0.7704(2) 0.46360(13) 0.2642(3) 0.0336(6) Uani 1 1 d . . . . .
H11 H 0.852483 0.457123 0.254193 0.040 Uiso 1 1 calc R U . . .
C12 C 0.6603(2) 0.41911(13) 0.1858(3) 0.0324(6) Uani 1 1 d . . . . .
H12 H 0.667700 0.382429 0.122162 0.039 Uiso 1 1 calc R U . . .
C13 C 0.6235(2) 0.24505(11) 0.3649(2) 0.0223(5) Uani 1 1 d . . . . .
C14 C 0.7303(2) 0.19254(11) 0.3788(2) 0.0224(5) Uani 1 1 d . . . . .
C15 C 0.7323(2) 0.14248(12) 0.2757(2) 0.0248(5) Uani 1 1 d . . . . .
H15 H 0.665323 0.136545 0.175141 0.030 Uiso 1 1 calc R U . . .
C16 C 0.8519(2) 0.17909(12) 0.5084(2) 0.0262(5) Uani 1 1 d . . . . .
C17 C 0.9059(2) 0.21927(14) 0.6548(3) 0.0373(6) Uani 1 1 d . . . . .
H17 H 0.835536 0.221608 0.694596 0.045 Uiso 1 1 calc R U . . .
C18 C 0.8963(3) 0.04709(13) 0.2776(3) 0.0365(6) Uani 1 1 d . . . . .
H18A H 0.971743 0.065717 0.258796 0.055 Uiso 1 1 calc R U . . .
H18B H 0.823421 0.031114 0.182159 0.055 Uiso 1 1 calc R U . . .
H18C H 0.927724 0.006334 0.347625 0.055 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C9 1.738(2) . ?
Cl2 C10 1.733(2) . ?
F1 C17 1.357(3) . ?
F2 C17 1.351(3) . ?
O1 C13 1.242(2) . ?
N1 H1 0.83(2) . ?
N1 C1 1.456(3) . ?
N1 C13 1.343(3) . ?
N2 N3 1.358(3) . ?
N2 C16 1.327(3) . ?
N3 C15 1.339(3) . ?
N3 C18 1.458(3) . ?
C1 H1A 1.0000 . ?
C1 C2 1.558(3) . ?
C1 C5 1.553(3) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C3 1.521(4) . ?
C3 H3 1.0000 . ?
C3 C4 1.542(3) . ?
C3 C6 1.546(4) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C5 1.557(3) . ?
C5 C6 1.554(3) . ?
C5 C7 1.494(3) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.387(3) . ?
C7 C12 1.396(3) . ?
C8 H8 0.9500 . ?
C8 C9 1.384(3) . ?
C9 C10 1.382(3) . ?
C10 C11 1.385(3) . ?
C11 H11 0.9500 . ?
C11 C12 1.389(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.482(3) . ?
C14 C15 1.380(3) . ?
C14 C16 1.413(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.496(3) . ?
C17 H17 1.0000 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 H1 120.1(16) . . ?
C13 N1 H1 116.8(16) . . ?
C13 N1 C1 123.11(19) . . ?
C16 N2 N3 104.24(17) . . ?
N2 N3 C18 119.54(18) . . ?
C15 N3 N2 112.47(18) . . ?
C15 N3 C18 127.88(19) . . ?
N1 C1 H1A 109.6 . . ?
N1 C1 C2 114.59(18) . . ?
N1 C1 C5 113.96(18) . . ?
C2 C1 H1A 109.6 . . ?
C5 C1 H1A 109.6 . . ?
C5 C1 C2 98.90(18) . . ?
C1 C2 H2A 111.9 . . ?
C1 C2 H2B 111.9 . . ?
H2A C2 H2B 109.6 . . ?
C3 C2 C1 99.26(19) . . ?
C3 C2 H2A 111.9 . . ?
C3 C2 H2B 111.9 . . ?
C2 C3 H3 119.8 . . ?
C2 C3 C4 102.2(2) . . ?
C2 C3 C6 102.44(19) . . ?
C4 C3 H3 119.8 . . ?
C4 C3 C6 86.81(19) . . ?
C6 C3 H3 119.8 . . ?
C3 C4 H4A 114.9 . . ?
C3 C4 H4B 114.9 . . ?
C3 C4 C5 82.53(17) . . ?
H4A C4 H4B 111.9 . . ?
C5 C4 H4A 114.9 . . ?
C5 C4 H4B 114.9 . . ?
C1 C5 C4 100.13(18) . . ?
C1 C5 C6 101.96(18) . . ?
C6 C5 C4 85.99(17) . . ?
C7 C5 C1 117.33(18) . . ?
C7 C5 C4 122.38(19) . . ?
C7 C5 C6 122.8(2) . . ?
C3 C6 C5 82.49(17) . . ?
C3 C6 H6A 114.9 . . ?
C3 C6 H6B 114.9 . . ?
C5 C6 H6A 114.9 . . ?
C5 C6 H6B 114.9 . . ?
H6A C6 H6B 111.9 . . ?
C8 C7 C5 119.7(2) . . ?
C8 C7 C12 118.4(2) . . ?
C12 C7 C5 121.9(2) . . ?
C7 C8 H8 119.7 . . ?
C9 C8 C7 120.6(2) . . ?
C9 C8 H8 119.7 . . ?
C8 C9 Cl1 118.48(18) . . ?
C10 C9 Cl1 120.65(18) . . ?
C10 C9 C8 120.9(2) . . ?
C9 C10 Cl2 120.38(18) . . ?
C9 C10 C11 119.3(2) . . ?
C11 C10 Cl2 120.30(18) . . ?
C10 C11 H11 120.0 . . ?
C10 C11 C12 120.0(2) . . ?
C12 C11 H11 120.0 . . ?
C7 C12 H12 119.5 . . ?
C11 C12 C7 120.9(2) . . ?
C11 C12 H12 119.5 . . ?
O1 C13 N1 122.9(2) . . ?
O1 C13 C14 120.12(18) . . ?
N1 C13 C14 116.90(18) . . ?
C15 C14 C13 129.36(19) . . ?
C15 C14 C16 103.71(19) . . ?
C16 C14 C13 126.80(19) . . ?
N3 C15 C14 107.49(19) . . ?
N3 C15 H15 126.3 . . ?
C14 C15 H15 126.3 . . ?
N2 C16 C14 112.09(19) . . ?
N2 C16 C17 120.43(19) . . ?
C14 C16 C17 127.4(2) . . ?
F1 C17 C16 109.7(2) . . ?
F1 C17 H17 110.0 . . ?
F2 C17 F1 106.6(2) . . ?
F2 C17 C16 110.5(2) . . ?
F2 C17 H17 110.0 . . ?
C16 C17 H17 110.0 . . ?
N3 C18 H18A 109.5 . . ?
N3 C18 H18B 109.5 . . ?
N3 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Cl1 C9 C10 Cl2 -3.2(3) . . . . ?
Cl1 C9 C10 C11 179.59(17) . . . . ?
Cl2 C10 C11 C12 -176.39(18) . . . . ?
O1 C13 C14 C15 158.5(2) . . . . ?
O1 C13 C14 C16 -16.5(3) . . . . ?
N1 C1 C2 C3 -123.0(2) . . . . ?
N1 C1 C5 C4 167.42(18) . . . . ?
N1 C1 C5 C6 79.4(2) . . . . ?
N1 C1 C5 C7 -57.8(3) . . . . ?
N1 C13 C14 C15 -19.3(3) . . . . ?
N1 C13 C14 C16 165.6(2) . . . . ?
N2 N3 C15 C14 -0.4(3) . . . . ?
N2 C16 C17 F1 109.7(2) . . . . ?
N2 C16 C17 F2 -7.6(3) . . . . ?
N3 N2 C16 C14 0.0(2) . . . . ?
N3 N2 C16 C17 -178.0(2) . . . . ?
C1 N1 C13 O1 -2.7(3) . . . . ?
C1 N1 C13 C14 175.08(18) . . . . ?
C1 C2 C3 C4 -43.7(2) . . . . ?
C1 C2 C3 C6 45.6(2) . . . . ?
C1 C5 C6 C3 65.16(19) . . . . ?
C1 C5 C7 C8 -94.1(2) . . . . ?
C1 C5 C7 C12 84.9(3) . . . . ?
C2 C1 C5 C4 45.4(2) . . . . ?
C2 C1 C5 C6 -42.6(2) . . . . ?
C2 C1 C5 C7 -179.81(19) . . . . ?
C2 C3 C4 C5 67.4(2) . . . . ?
C2 C3 C6 C5 -67.09(19) . . . . ?
C3 C4 C5 C1 -66.99(19) . . . . ?
C3 C4 C5 C6 34.46(18) . . . . ?
C3 C4 C5 C7 161.3(2) . . . . ?
C4 C3 C6 C5 34.72(17) . . . . ?
C4 C5 C6 C3 -34.36(17) . . . . ?
C4 C5 C7 C8 30.1(3) . . . . ?
C4 C5 C7 C12 -150.9(2) . . . . ?
C5 C1 C2 C3 -1.4(2) . . . . ?
C5 C7 C8 C9 178.9(2) . . . . ?
C5 C7 C12 C11 -179.2(2) . . . . ?
C6 C3 C4 C5 -34.63(17) . . . . ?
C6 C5 C7 C8 138.2(2) . . . . ?
C6 C5 C7 C12 -42.8(3) . . . . ?
C7 C5 C6 C3 -160.8(2) . . . . ?
C7 C8 C9 Cl1 -179.93(16) . . . . ?
C7 C8 C9 C10 0.8(3) . . . . ?
C8 C7 C12 C11 -0.1(3) . . . . ?
C8 C9 C10 Cl2 176.11(17) . . . . ?
C8 C9 C10 C11 -1.1(3) . . . . ?
C9 C10 C11 C12 0.9(3) . . . . ?
C10 C11 C12 C7 -0.2(4) . . . . ?
C12 C7 C8 C9 -0.1(3) . . . . ?
C13 N1 C1 C2 -134.3(2) . . . . ?
C13 N1 C1 C5 112.8(2) . . . . ?
C13 C14 C15 N3 -175.5(2) . . . . ?
C13 C14 C16 N2 175.8(2) . . . . ?
C13 C14 C16 C17 -6.4(4) . . . . ?
C14 C16 C17 F1 -68.0(3) . . . . ?
C14 C16 C17 F2 174.8(2) . . . . ?
C15 C14 C16 N2 -0.2(2) . . . . ?
C15 C14 C16 C17 177.6(2) . . . . ?
C16 N2 N3 C15 0.2(2) . . . . ?
C16 N2 N3 C18 176.8(2) . . . . ?
C16 C14 C15 N3 0.4(2) . . . . ?
C18 N3 C15 C14 -176.6(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_v75
_audit_block_doi                 10.5517/ccdc.csd.cc2gr9xg
_database_code_depnum_ccdc_archive 'CCDC 2286526'
loop_
_citation_id
_citation_doi
_citation_year
1 10.26434/chemrxiv-2023-78z7p 2023
loop_
_audit_author_name
_audit_author_address
'Iryna Sadkova'
;Enamine Ltd
Ukraine
;
_audit_update_record             
;
2023-08-03 deposited with the CCDC.	2023-10-27 downloaded from the CCDC.
;
_audit_creation_date             2022-12-12
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C13 H13 F O2'
_chemical_formula_sum            'C13 H13 F O2'
_chemical_formula_weight         220.23
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   12.2300(9)
_cell_length_b                   6.3052(5)
_cell_length_c                   14.0798(10)
_cell_angle_alpha                90
_cell_angle_beta                 90.886(5)
_cell_angle_gamma                90
_cell_volume                     1085.60(14)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1457
_cell_measurement_temperature    273.15
_cell_measurement_theta_max      19.03
_cell_measurement_theta_min      2.19
_shelx_estimated_absorpt_T_max   0.995
_shelx_estimated_absorpt_T_min   0.985
_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'light yellow'
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.347
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             464
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0709
_diffrn_reflns_av_unetI/netI     0.0487
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            15155
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         2.189
_diffrn_ambient_temperature      273.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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                1207
_reflns_number_total             1917
_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 2016/6 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.146
_refine_diff_density_min         -0.173
_refine_diff_density_rms         0.033
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     146
_refine_ls_number_reflns         1917
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0897
_refine_ls_R_factor_gt           0.0479
_refine_ls_restrained_S_all      1.019
_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)+(0.0347P)²+0.2835P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0918
_refine_ls_wR_factor_ref         0.1066
_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.a Ternary CH refined with riding coordinates:
 C1(H1), C4(H4)
2.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C5(H5A,H5B), C6(H6A,H6B)
2.c Aromatic/amide H refined with riding coordinates:
 C9(H9), C10(H10), C12(H12), C13(H13)
2.d Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.92187(12) 0.7695(3) 0.15110(10) 0.0867(6) Uani 1 1 d . . . . .
O1 O 0.61347(12) 0.9519(3) 0.56672(11) 0.0562(5) Uani 1 1 d . . . . .
O2 O 0.54345(13) 0.7513(3) 0.45098(11) 0.0556(5) Uani 1 1 d . . . . .
H2 H 0.502562 0.853674 0.444966 0.083 Uiso 1 1 calc R U . . .
C1 C 0.67853(17) 0.5933(3) 0.54911(14) 0.0402(6) Uani 1 1 d . . . . .
H1 H 0.649666 0.467096 0.516740 0.048 Uiso 1 1 calc R U . . .
C2 C 0.80283(16) 0.6171(3) 0.52836(14) 0.0383(5) Uani 1 1 d . . . . .
C3 C 0.8474(2) 0.4219(4) 0.58426(16) 0.0560(7) Uani 1 1 d . . . . .
H3A H 0.807080 0.291364 0.573597 0.067 Uiso 1 1 calc R U . . .
H3B H 0.925734 0.400483 0.580318 0.067 Uiso 1 1 calc R U . . .
C4 C 0.8104(2) 0.5528(4) 0.67127(16) 0.0567(7) Uani 1 1 d . . . . .
H4 H 0.843118 0.525714 0.734085 0.068 Uiso 1 1 calc R U . . .
C5 C 0.68715(19) 0.5508(4) 0.65811(15) 0.0555(7) Uani 1 1 d . . . . .
H5A H 0.652482 0.662077 0.694461 0.067 Uiso 1 1 calc R U . . .
H5B H 0.655958 0.414678 0.674933 0.067 Uiso 1 1 calc R U . . .
C6 C 0.84408(18) 0.7503(4) 0.61450(15) 0.0502(6) Uani 1 1 d . . . . .
H6A H 0.921942 0.779689 0.615284 0.060 Uiso 1 1 calc R U . . .
H6B H 0.801413 0.876583 0.627242 0.060 Uiso 1 1 calc R U . . .
C7 C 0.60967(16) 0.7820(4) 0.52365(15) 0.0397(5) Uani 1 1 d . . . . .
C8 C 0.83506(16) 0.6608(4) 0.42826(15) 0.0390(5) Uani 1 1 d . . . . .
C9 C 0.87380(18) 0.8574(4) 0.40019(16) 0.0500(6) Uani 1 1 d . . . . .
H9 H 0.879413 0.966323 0.444515 0.060 Uiso 1 1 calc R U . . .
C10 C 0.90433(19) 0.8944(4) 0.30712(18) 0.0589(7) Uani 1 1 d . . . . .
H10 H 0.930266 1.026588 0.288767 0.071 Uiso 1 1 calc R U . . .
C11 C 0.89553(19) 0.7336(5) 0.24357(17) 0.0559(7) Uani 1 1 d . . . . .
C12 C 0.85925(19) 0.5364(5) 0.26737(17) 0.0600(7) Uani 1 1 d . . . . .
H12 H 0.855090 0.428454 0.222455 0.072 Uiso 1 1 calc R U . . .
C13 C 0.82869(18) 0.5015(4) 0.36066(16) 0.0516(6) Uani 1 1 d . . . . .
H13 H 0.803379 0.368260 0.378134 0.062 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
F1 C11 1.365(3) . ?
O1 C7 1.231(2) . ?
O2 H2 0.8200 . ?
O2 C7 1.309(2) . ?
C1 H1 0.9800 . ?
C1 C2 1.560(3) . ?
C1 C5 1.560(3) . ?
C1 C7 1.498(3) . ?
C2 C3 1.555(3) . ?
C2 C6 1.553(3) . ?
C2 C8 1.495(3) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 C4 1.550(3) . ?
C4 H4 0.9800 . ?
C4 C5 1.516(3) . ?
C4 C6 1.540(3) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C8 C9 1.387(3) . ?
C8 C13 1.385(3) . ?
C9 H9 0.9300 . ?
C9 C10 1.388(3) . ?
C10 H10 0.9300 . ?
C10 C11 1.355(3) . ?
C11 C12 1.364(3) . ?
C12 H12 0.9300 . ?
C12 C13 1.389(3) . ?
C13 H13 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7 O2 H2 109.5 . . ?
C2 C1 H1 109.7 . . ?
C2 C1 C5 98.60(16) . . ?
C5 C1 H1 109.7 . . ?
C7 C1 H1 109.7 . . ?
C7 C1 C2 115.12(17) . . ?
C7 C1 C5 113.65(18) . . ?
C3 C2 C1 99.43(17) . . ?
C6 C2 C1 102.22(16) . . ?
C6 C2 C3 85.74(16) . . ?
C8 C2 C1 117.79(16) . . ?
C8 C2 C3 121.83(18) . . ?
C8 C2 C6 123.34(18) . . ?
C2 C3 H3A 114.8 . . ?
C2 C3 H3B 114.8 . . ?
H3A C3 H3B 111.9 . . ?
C4 C3 C2 82.78(17) . . ?
C4 C3 H3A 114.8 . . ?
C4 C3 H3B 114.8 . . ?
C3 C4 H4 120.0 . . ?
C5 C4 C3 101.59(19) . . ?
C5 C4 H4 120.0 . . ?
C5 C4 C6 102.51(18) . . ?
C6 C4 C3 86.37(17) . . ?
C6 C4 H4 120.0 . . ?
C1 C5 H5A 111.8 . . ?
C1 C5 H5B 111.8 . . ?
C4 C5 C1 99.84(17) . . ?
C4 C5 H5A 111.8 . . ?
C4 C5 H5B 111.8 . . ?
H5A C5 H5B 109.5 . . ?
C2 C6 H6A 114.8 . . ?
C2 C6 H6B 114.8 . . ?
C4 C6 C2 83.20(17) . . ?
C4 C6 H6A 114.8 . . ?
C4 C6 H6B 114.8 . . ?
H6A C6 H6B 111.8 . . ?
O1 C7 O2 122.1(2) . . ?
O1 C7 C1 123.8(2) . . ?
O2 C7 C1 114.1(2) . . ?
C9 C8 C2 122.0(2) . . ?
C13 C8 C2 120.1(2) . . ?
C13 C8 C9 117.9(2) . . ?
C8 C9 H9 119.4 . . ?
C8 C9 C10 121.2(2) . . ?
C10 C9 H9 119.4 . . ?
C9 C10 H10 120.7 . . ?
C11 C10 C9 118.5(2) . . ?
C11 C10 H10 120.7 . . ?
C10 C11 F1 119.2(3) . . ?
C10 C11 C12 122.9(2) . . ?
C12 C11 F1 117.9(3) . . ?
C11 C12 H12 121.0 . . ?
C11 C12 C13 118.0(2) . . ?
C13 C12 H12 121.0 . . ?
C8 C13 C12 121.5(2) . . ?
C8 C13 H13 119.3 . . ?
C12 C13 H13 119.3 . . ?

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
F1 C11 C12 C13 -177.75(19) . . . . ?
C1 C2 C3 C4 -67.58(17) . . . . ?
C1 C2 C6 C4 64.38(17) . . . . ?
C1 C2 C8 C9 107.9(2) . . . . ?
C1 C2 C8 C13 -73.3(3) . . . . ?
C2 C1 C5 C4 -1.9(2) . . . . ?
C2 C1 C7 O1 -70.0(3) . . . . ?
C2 C1 C7 O2 110.4(2) . . . . ?
C2 C3 C4 C5 67.61(19) . . . . ?
C2 C3 C4 C6 -34.43(16) . . . . ?
C2 C8 C9 C10 179.4(2) . . . . ?
C2 C8 C13 C12 -179.23(19) . . . . ?
C3 C2 C6 C4 -34.36(16) . . . . ?
C3 C2 C8 C9 -129.0(2) . . . . ?
C3 C2 C8 C13 49.7(3) . . . . ?
C3 C4 C5 C1 -43.1(2) . . . . ?
C3 C4 C6 C2 34.45(16) . . . . ?
C5 C1 C2 C3 46.11(19) . . . . ?
C5 C1 C2 C6 -41.5(2) . . . . ?
C5 C1 C2 C8 179.89(19) . . . . ?
C5 C1 C7 O1 42.7(3) . . . . ?
C5 C1 C7 O2 -137.0(2) . . . . ?
C5 C4 C6 C2 -66.62(18) . . . . ?
C6 C2 C3 C4 34.13(16) . . . . ?
C6 C2 C8 C9 -21.4(3) . . . . ?
C6 C2 C8 C13 157.4(2) . . . . ?
C6 C4 C5 C1 45.7(2) . . . . ?
C7 C1 C2 C3 167.37(18) . . . . ?
C7 C1 C2 C6 79.7(2) . . . . ?
C7 C1 C2 C8 -58.8(3) . . . . ?
C7 C1 C5 C4 -124.3(2) . . . . ?
C8 C2 C3 C4 161.2(2) . . . . ?
C8 C2 C6 C4 -160.1(2) . . . . ?
C8 C9 C10 C11 0.0(3) . . . . ?
C9 C8 C13 C12 -0.4(3) . . . . ?
C9 C10 C11 F1 177.9(2) . . . . ?
C9 C10 C11 C12 -0.8(4) . . . . ?
C10 C11 C12 C13 1.0(4) . . . . ?
C11 C12 C13 C8 -0.3(3) . . . . ?
C13 C8 C9 C10 0.6(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
