# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_8
_database_code_depnum_ccdc_archive 'CCDC 2193041'
loop_
_audit_author_name
_audit_author_address
'Valentyna D. Slyusarchuk'
;Keele University
United Kingdom
;
_audit_update_record             
;
2022-07-27 deposited with the CCDC.	2022-11-14 downloaded from the CCDC.
;
_audit_creation_date             2022-07-19
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C10 H15 F O3'
_chemical_formula_sum            'C10 H15 F O3'
_chemical_formula_weight         202.22
_chemical_absolute_configuration syn
_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      trigonal
_space_group_IT_number           145
_space_group_name_H-M_alt        'P 32'
_space_group_name_Hall           'P 32'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z+2/3'
'-x+y, -x, z+1/3'

_cell_length_a                   11.884(3)
_cell_length_b                   11.884(3)
_cell_length_c                   6.298(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     770.2(4)
_cell_formula_units_Z            3
_cell_measurement_reflns_used    3645
_cell_measurement_temperature    150.0
_cell_measurement_theta_max      25.298
_cell_measurement_theta_min      3.429
_shelx_estimated_absorpt_T_max   0.990
_shelx_estimated_absorpt_T_min   0.984
_exptl_absorpt_coefficient_mu    0.106
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6906
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0645 before and 0.0583 after correction.
The Ratio of minimum to maximum transmission is 0.9256.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.308
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             324
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.09
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0724
_diffrn_reflns_av_unetI/netI     0.0742
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            15475
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.522
_diffrn_reflns_theta_min         3.429
_diffrn_ambient_temperature      150.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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           20.0
_diffrn_source_power             1.0
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.999
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                2179
_reflns_number_total             3119
_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       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.179
_refine_diff_density_min         -0.225
_refine_diff_density_rms         0.048
_refine_ls_abs_structure_details 
;
 Flack x determined using 767 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.0(5)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     132
_refine_ls_number_reflns         3119
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0914
_refine_ls_R_factor_gt           0.0542
_refine_ls_restrained_S_all      1.053
_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)+(0.0296P)²+0.0876P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0805
_refine_ls_wR_factor_ref         0.0896
_refine_special_details          ?
_olex2_refinement_description    
;
1. Others
 Fixed Uiso: H2(0.025) H3(0.023) H4(0.025) H5(0.03) H6(0.038) H7A(0.056)
 H7B(0.056) H1(0.069) H1A(0.029) H10A(0.051) H10B(0.051) H10C(0.051) H9A(0.048)
 H9B(0.048) H9C(0.048)
 Fixed X: H2(-0.008215) H3(0.133916) H4(0.268729) H5(0.276467) H6(0.079506)
 H7A(0.153134) H7B(0.057262) H1A(0.049649) H10A(0.35579) H10B(0.413731)
 H10C(0.504266) H9A(0.54954) H9B(0.453169) H9C(0.428743)
 Fixed Y: H2(0.212486) H3(0.182417) H4(0.402198) H5(0.508008) H6(0.51265)
 H7A(0.466891) H7B(0.526648) H1A(0.343358) H10A(0.248236) H10B(0.164586)
 H10C(0.31839) H9A(0.331502) H9B(0.178332) H9C(0.277647)
 Fixed Z: H2(0.424265) H3(0.226254) H4(0.203132) H5(0.578672) H6(0.476395)
 H7A(0.086989) H7B(0.136174) H1A(0.715272) H10A(0.101075) H10B(0.203271)
 H10C(0.176164) H9A(0.579264) H9B(0.602093) H9C(0.7388)
;
_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 0.19267(17) 0.31495(17) 0.8138(2) 0.0297(4) Uani 1 1 d . . . . .
O1 O -0.00982(18) 0.0869(2) 0.6242(3) 0.0242(5) Uani 1 1 d D . . . .
O2 O 0.24345(19) 0.17533(18) 0.4678(3) 0.0221(5) Uani 1 1 d . . . . .
O3 O 0.38030(19) 0.39097(18) 0.4363(3) 0.0235(5) Uani 1 1 d . . . . .
C1 C 0.0573(3) 0.2066(3) 0.5162(4) 0.0205(6) Uani 1 1 d . . . . .
H2 H -0.008215 0.212486 0.424265 0.025 Uiso 1 1 calc R U . . .
C2 C 0.1671(3) 0.2229(3) 0.3685(4) 0.0195(6) Uani 1 1 d . . . . .
H3 H 0.133916 0.182417 0.226254 0.023 Uiso 1 1 calc R U . . .
C3 C 0.2595(3) 0.3706(3) 0.3528(4) 0.0211(6) Uani 1 1 d . . . . .
H4 H 0.268729 0.402198 0.203132 0.025 Uiso 1 1 calc R U . . .
C4 C 0.2039(3) 0.4351(3) 0.4989(5) 0.0246(7) Uani 1 1 d . . . . .
H5 H 0.276467 0.508008 0.578672 0.030 Uiso 1 1 calc R U . . .
C5 C 0.1248(3) 0.4844(3) 0.3867(5) 0.0315(7) Uani 1 1 d . . . . .
H6 H 0.079506 0.512650 0.476395 0.038 Uiso 1 1 calc R U . . .
C6 C 0.1105(4) 0.4934(4) 0.1857(6) 0.0463(10) Uani 1 1 d . . . . .
H7A H 0.153134 0.466891 0.086989 0.056 Uiso 1 1 calc R U . . .
H7B H 0.057262 0.526648 0.136174 0.056 Uiso 1 1 calc R U . . .
H1 H 0.046(3) 0.085(4) 0.724(6) 0.069 Uiso 1 1 d D U . . .
C7 C 0.1179(3) 0.3273(3) 0.6534(4) 0.0240(6) Uani 1 1 d . . . . .
H1A H 0.049649 0.343358 0.715272 0.029 Uiso 1 1 calc R U . . .
C8 C 0.3759(3) 0.2686(3) 0.4270(5) 0.0216(6) Uani 1 1 d . . . . .
C9 C 0.4160(3) 0.2481(3) 0.2073(5) 0.0339(8) Uani 1 1 d . . . . .
H10A H 0.355790 0.248236 0.101075 0.051 Uiso 1 1 calc R U . . .
H10B H 0.413731 0.164586 0.203271 0.051 Uiso 1 1 calc R U . . .
H10C H 0.504266 0.318390 0.176164 0.051 Uiso 1 1 calc R U . . .
C10 C 0.4591(3) 0.2636(3) 0.6020(5) 0.0322(8) Uani 1 1 d . . . . .
H9A H 0.549540 0.331502 0.579264 0.048 Uiso 1 1 calc R U . . .
H9B H 0.453169 0.178332 0.602093 0.048 Uiso 1 1 calc R U . . .
H9C H 0.428743 0.277647 0.738800 0.048 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 C7 1.401(3) . ?
O1 C1 1.410(3) . ?
O1 H1 0.92(3) . ?
O2 C2 1.431(3) . ?
O2 C8 1.424(3) . ?
O3 C3 1.431(3) . ?
O3 C8 1.430(3) . ?
C1 H2 1.0000 . ?
C1 C2 1.534(4) . ?
C2 H3 1.0000 . ?
C2 C3 1.539(4) . ?
C3 H4 1.0000 . ?
C3 C4 1.541(4) . ?
C4 H5 1.0000 . ?
C4 C5 1.509(5) . ?
C5 H6 0.9500 . ?
C5 C6 1.289(4) . ?
C6 H7A 0.9500 . ?
C6 H7B 0.9500 . ?
C7 C1 1.513(4) . ?
C7 C4 1.524(4) . ?
C7 H1A 1.0000 . ?
C8 C9 1.522(4) . ?
C8 C10 1.501(4) . ?
C9 H10A 0.9800 . ?
C9 H10B 0.9800 . ?
C9 H10C 0.9800 . ?
C10 H9A 0.9800 . ?
C10 H9B 0.9800 . ?
C10 H9C 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 O1 H1 107(3) . . ?
C8 O2 C2 106.6(2) . . ?
C8 O3 C3 106.8(2) . . ?
O1 C1 H2 106.4 . . ?
O1 C1 C2 115.9(2) . . ?
O1 C1 C7 116.2(2) . . ?
C2 C1 H2 106.4 . . ?
C7 C1 H2 106.4 . . ?
C7 C1 C2 104.8(2) . . ?
O2 C2 C1 110.6(2) . . ?
O2 C2 H3 112.1 . . ?
O2 C2 C3 104.3(2) . . ?
C1 C2 H3 112.1 . . ?
C1 C2 C3 105.1(2) . . ?
C3 C2 H3 112.1 . . ?
O3 C3 C2 104.6(2) . . ?
O3 C3 H4 111.7 . . ?
O3 C3 C4 109.9(2) . . ?
C2 C3 H4 111.7 . . ?
C2 C3 C4 106.8(2) . . ?
C4 C3 H4 111.7 . . ?
C3 C4 H5 109.4 . . ?
C5 C4 C3 114.8(2) . . ?
C5 C4 H5 109.4 . . ?
C5 C4 C7 109.8(3) . . ?
C7 C4 C3 103.8(2) . . ?
C7 C4 H5 109.4 . . ?
C4 C5 H6 115.6 . . ?
C6 C5 C4 128.8(3) . . ?
C6 C5 H6 115.6 . . ?
C5 C6 H7A 120.0 . . ?
C5 C6 H7B 120.0 . . ?
H7A C6 H7B 120.0 . . ?
F1 C7 C1 109.8(2) . . ?
F1 C7 C4 110.7(2) . . ?
F1 C7 H1A 110.9 . . ?
C1 C7 C4 103.5(2) . . ?
C1 C7 H1A 110.9 . . ?
C4 C7 H1A 110.9 . . ?
O2 C8 O3 104.4(2) . . ?
O2 C8 C9 110.7(2) . . ?
O2 C8 C10 109.3(2) . . ?
O3 C8 C9 110.1(2) . . ?
O3 C8 C10 108.7(2) . . ?
C10 C8 C9 113.3(3) . . ?
C8 C9 H10A 109.5 . . ?
C8 C9 H10B 109.5 . . ?
C8 C9 H10C 109.5 . . ?
H10A C9 H10B 109.5 . . ?
H10A C9 H10C 109.5 . . ?
H10B C9 H10C 109.5 . . ?
C8 C10 H9A 109.5 . . ?
C8 C10 H9B 109.5 . . ?
C8 C10 H9C 109.5 . . ?
H9A C10 H9B 109.5 . . ?
H9A C10 H9C 109.5 . . ?
H9B C10 H9C 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 C7 C1 O1 50.7(3) . . . . ?
F1 C7 C1 C2 -78.6(3) . . . . ?
F1 C7 C4 C3 80.0(3) . . . . ?
F1 C7 C4 C5 -156.9(2) . . . . ?
O1 C1 C2 O2 -43.3(3) . . . . ?
O1 C1 C2 C3 -155.3(2) . . . . ?
O2 C2 C3 O3 2.4(3) . . . . ?
O2 C2 C3 C4 -114.1(2) . . . . ?
O3 C3 C4 C5 148.9(3) . . . . ?
O3 C3 C4 C7 -91.4(3) . . . . ?
C1 C2 C3 O3 118.9(2) . . . . ?
C1 C2 C3 C4 2.4(3) . . . . ?
C1 C7 C4 C3 -37.6(3) . . . . ?
C1 C7 C4 C5 85.5(3) . . . . ?
C2 O2 C8 O3 36.4(3) . . . . ?
C2 O2 C8 C9 -82.1(3) . . . . ?
C2 O2 C8 C10 152.5(2) . . . . ?
C2 C3 C4 C5 -98.2(3) . . . . ?
C2 C3 C4 C7 21.6(3) . . . . ?
C3 O3 C8 O2 -34.7(3) . . . . ?
C3 O3 C8 C9 84.1(3) . . . . ?
C3 O3 C8 C10 -151.2(2) . . . . ?
C3 C4 C5 C6 -8.9(5) . . . . ?
C4 C7 C1 O1 168.9(2) . . . . ?
C4 C7 C1 C2 39.7(3) . . . . ?
C7 C1 C2 O2 86.2(3) . . . . ?
C7 C1 C2 C3 -25.8(3) . . . . ?
C7 C4 C5 C6 -125.3(4) . . . . ?
C8 O2 C2 C1 -136.2(2) . . . . ?
C8 O2 C2 C3 -23.7(3) . . . . ?
C8 O3 C3 C2 19.6(3) . . . . ?
C8 O3 C3 C4 133.9(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_10
_database_code_depnum_ccdc_archive 'CCDC 2218823'
loop_
_audit_author_name
_audit_author_address
'Valentyna Slyusarchuk'
;Keele University
United Kingdom
;
_audit_update_record             
;
2022-11-10 deposited with the CCDC.	2022-11-14 downloaded from the CCDC.
;
_audit_creation_date             2022-08-10
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H17 F N2 O8'
_chemical_formula_sum            'C17 H17 F N2 O8'
_chemical_formula_weight         396.32
_chemical_absolute_configuration syn
_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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   6.3601(4)
_cell_length_b                   9.4921(6)
_cell_length_c                   29.8749(18)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1803.57(19)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3916
_cell_measurement_temperature    150.0
_cell_measurement_theta_max      23.479
_cell_measurement_theta_min      2.96
_shelx_estimated_absorpt_T_max   0.999
_shelx_estimated_absorpt_T_min   0.975
_exptl_absorpt_coefficient_mu    0.123
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6764
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0695 before and 0.0642 after correction.
The Ratio of minimum to maximum transmission is 0.9072.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.460
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             824
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.01
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1131
_diffrn_reflns_av_unetI/netI     0.0901
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_number            26730
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.494
_diffrn_reflns_theta_min         3.275
_diffrn_ambient_temperature      150.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.998
_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           20.0
_diffrn_source_power             1.0
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.720
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                2904
_reflns_number_total             4133
_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       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.260
_refine_diff_density_min         -0.310
_refine_diff_density_rms         0.058
_refine_ls_abs_structure_details 
;
 Flack x determined using 827 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.4(7)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.140
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     255
_refine_ls_number_reflns         4133
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1134
_refine_ls_R_factor_gt           0.0716
_refine_ls_restrained_S_all      1.140
_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)+(0.0267P)²+0.4503P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0921
_refine_ls_wR_factor_ref         0.1010
_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(H1), C2(H2), C3(H3), C4(H4), C5(H5)
2.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C13(H13), C15(H15), C17(H17)
2.c X=CH2 refined with riding coordinates:
 C7(H7A,H7B)
2.d Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C10(H10A,H10B,H10C)
;
_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 -0.0920(4) -0.1296(3) -0.55182(8) 0.0323(7) Uani 1 1 d . . . . .
O1 O -0.6720(5) -0.3477(3) -0.57752(9) 0.0245(7) Uani 1 1 d . . . . .
O2 O -0.4165(5) -0.4584(3) -0.61740(9) 0.0219(7) Uani 1 1 d . . . . .
O3 O -0.3690(5) -0.1992(3) -0.65314(8) 0.0192(7) Uani 1 1 d . . . . .
O4 O -0.1790(5) -0.3261(3) -0.70270(9) 0.0224(7) Uani 1 1 d . . . . .
O5 O -1.0085(5) 0.0243(3) -0.69157(10) 0.0368(8) Uani 1 1 d . . . . .
O6 O -1.1608(5) -0.0184(3) -0.75487(10) 0.0278(7) Uani 1 1 d . . . . .
O7 O -0.7796(5) -0.2644(3) -0.87013(9) 0.0282(8) Uani 1 1 d . . . . .
O8 O -0.4815(5) -0.3629(3) -0.85449(9) 0.0299(8) Uani 1 1 d . . . . .
N1 N -1.0140(6) -0.0296(3) -0.72883(12) 0.0209(8) Uani 1 1 d . . . . .
N2 N -0.6359(7) -0.2923(4) -0.84459(12) 0.0240(9) Uani 1 1 d . . . . .
C1 C -0.2240(7) -0.2330(4) -0.61694(12) 0.0194(10) Uani 1 1 d . . . . .
H1 H -0.075694 -0.246451 -0.627203 0.023 Uiso 1 1 calc R U . . .
C2 C -0.3105(7) -0.3584(4) -0.59039(13) 0.0211(10) Uani 1 1 d . . . . .
H2 H -0.196171 -0.404619 -0.572720 0.025 Uiso 1 1 calc R U . . .
C3 C -0.4790(7) -0.2962(4) -0.55904(13) 0.0210(10) Uani 1 1 d . . . . .
H3 H -0.459109 -0.328524 -0.527467 0.025 Uiso 1 1 calc R U . . .
C4 C -0.4647(7) -0.1353(4) -0.56280(13) 0.0208(10) Uani 1 1 d . . . . .
H4 H -0.574834 -0.103222 -0.584409 0.025 Uiso 1 1 calc R U . . .
C5 C -0.2504(7) -0.1111(4) -0.58425(13) 0.0220(10) Uani 1 1 d . . . . .
H5 H -0.240857 -0.017426 -0.599405 0.026 Uiso 1 1 calc R U . . .
C6 C -0.4937(8) -0.0553(4) -0.52017(14) 0.0251(11) Uani 1 1 d . . . . .
H6 H -0.411985 -0.082455 -0.494987 0.030 Uiso 1 1 calc R U . . .
C7 C -0.6259(8) 0.0506(4) -0.51536(16) 0.0337(13) Uani 1 1 d . . . . .
H7A H -0.709828 0.080254 -0.539924 0.040 Uiso 1 1 calc R U . . .
H7B H -0.637152 0.097344 -0.487344 0.040 Uiso 1 1 calc R U . . .
C8 C -0.6226(7) -0.4796(4) -0.59795(14) 0.0234(10) Uani 1 1 d . . . . .
C9 C -0.7750(7) -0.5071(5) -0.63544(14) 0.0331(12) Uani 1 1 d . . . . .
H9A H -0.767896 -0.429861 -0.657157 0.050 Uiso 1 1 calc R U . . .
H9B H -0.917899 -0.513454 -0.623330 0.050 Uiso 1 1 calc R U . . .
H9C H -0.738542 -0.595894 -0.650264 0.050 Uiso 1 1 calc R U . . .
C10 C -0.6132(8) -0.5973(4) -0.56380(14) 0.0313(12) Uani 1 1 d . . . . .
H10A H -0.755126 -0.617150 -0.552703 0.047 Uiso 1 1 calc R U . . .
H10B H -0.523139 -0.568776 -0.538771 0.047 Uiso 1 1 calc R U . . .
H10C H -0.555188 -0.682150 -0.577827 0.047 Uiso 1 1 calc R U . . .
C11 C -0.3335(7) -0.2584(4) -0.69316(12) 0.0163(9) Uani 1 1 d . . . . .
C12 C -0.5057(7) -0.2230(4) -0.72496(12) 0.0151(9) Uani 1 1 d . . . . .
C13 C -0.6774(7) -0.1438(4) -0.71182(13) 0.0175(10) Uani 1 1 d . . . . .
H13 H -0.689578 -0.110779 -0.681917 0.021 Uiso 1 1 calc R U . . .
C14 C -0.8303(7) -0.1138(4) -0.74300(13) 0.0160(9) Uani 1 1 d . . . . .
C15 C -0.8217(7) -0.1591(4) -0.78676(13) 0.0179(9) Uani 1 1 d . . . . .
H15 H -0.929006 -0.137313 -0.807753 0.021 Uiso 1 1 calc R U . . .
C16 C -0.6475(7) -0.2382(4) -0.79829(12) 0.0180(10) Uani 1 1 d . . . . .
C17 C -0.4879(8) -0.2710(4) -0.76878(12) 0.0172(9) Uani 1 1 d . . . . .
H17 H -0.369692 -0.324743 -0.778105 0.021 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 1.408(4) . ?
O1 C3 1.432(5) . ?
O1 C8 1.428(5) . ?
O2 C2 1.417(5) . ?
O2 C8 1.448(5) . ?
O3 C1 1.457(4) . ?
O3 C11 1.340(4) . ?
O4 C11 1.208(5) . ?
O5 N1 1.226(4) . ?
O6 N1 1.220(4) . ?
O7 N2 1.220(4) . ?
O8 N2 1.225(5) . ?
N1 C14 1.478(5) . ?
N2 C16 1.477(5) . ?
C1 H1 1.0000 . ?
C1 C2 1.533(6) . ?
C1 C5 1.523(5) . ?
C2 H2 1.0000 . ?
C2 C3 1.541(6) . ?
C3 H3 1.0000 . ?
C3 C4 1.534(6) . ?
C4 H4 1.0000 . ?
C4 C5 1.524(6) . ?
C4 C6 1.494(5) . ?
C5 H5 1.0000 . ?
C6 H6 0.9500 . ?
C6 C7 1.318(6) . ?
C7 H7A 0.9500 . ?
C7 H7B 0.9500 . ?
C8 C9 1.504(6) . ?
C8 C10 1.514(6) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 C12 1.488(6) . ?
C12 C13 1.383(6) . ?
C12 C17 1.391(5) . ?
C13 H13 0.9500 . ?
C13 C14 1.376(5) . ?
C14 C15 1.377(5) . ?
C15 H15 0.9500 . ?
C15 C16 1.382(6) . ?
C16 C17 1.380(6) . ?
C17 H17 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C8 O1 C3 106.0(3) . . ?
C2 O2 C8 107.2(3) . . ?
C11 O3 C1 117.6(3) . . ?
O5 N1 C14 117.6(4) . . ?
O6 N1 O5 124.4(4) . . ?
O6 N1 C14 118.0(3) . . ?
O7 N2 O8 124.6(4) . . ?
O7 N2 C16 118.2(4) . . ?
O8 N2 C16 117.1(4) . . ?
O3 C1 H1 113.4 . . ?
O3 C1 C2 109.1(3) . . ?
O3 C1 C5 103.8(3) . . ?
C2 C1 H1 113.4 . . ?
C5 C1 H1 113.4 . . ?
C5 C1 C2 102.6(3) . . ?
O2 C2 C1 113.4(3) . . ?
O2 C2 H2 110.7 . . ?
O2 C2 C3 105.8(3) . . ?
C1 C2 H2 110.7 . . ?
C1 C2 C3 105.4(3) . . ?
C3 C2 H2 110.7 . . ?
O1 C3 C2 103.3(3) . . ?
O1 C3 H3 111.6 . . ?
O1 C3 C4 111.3(4) . . ?
C2 C3 H3 111.6 . . ?
C4 C3 C2 107.2(4) . . ?
C4 C3 H3 111.6 . . ?
C3 C4 H4 108.0 . . ?
C5 C4 C3 103.5(4) . . ?
C5 C4 H4 108.0 . . ?
C6 C4 C3 115.9(3) . . ?
C6 C4 H4 108.0 . . ?
C6 C4 C5 113.1(4) . . ?
F1 C5 C1 105.6(3) . . ?
F1 C5 C4 109.4(3) . . ?
F1 C5 H5 112.2 . . ?
C1 C5 C4 104.7(3) . . ?
C1 C5 H5 112.2 . . ?
C4 C5 H5 112.2 . . ?
C4 C6 H6 118.0 . . ?
C7 C6 C4 124.0(4) . . ?
C7 C6 H6 118.0 . . ?
C6 C7 H7A 120.0 . . ?
C6 C7 H7B 120.0 . . ?
H7A C7 H7B 120.0 . . ?
O1 C8 O2 104.4(3) . . ?
O1 C8 C9 109.2(4) . . ?
O1 C8 C10 111.6(3) . . ?
O2 C8 C9 108.0(3) . . ?
O2 C8 C10 109.7(4) . . ?
C9 C8 C10 113.5(4) . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C8 C10 H10A 109.5 . . ?
C8 C10 H10B 109.5 . . ?
C8 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
O3 C11 C12 110.6(4) . . ?
O4 C11 O3 124.8(4) . . ?
O4 C11 C12 124.6(4) . . ?
C13 C12 C11 121.5(3) . . ?
C13 C12 C17 120.6(4) . . ?
C17 C12 C11 117.9(4) . . ?
C12 C13 H13 120.7 . . ?
C14 C13 C12 118.6(4) . . ?
C14 C13 H13 120.7 . . ?
C13 C14 N1 118.5(3) . . ?
C13 C14 C15 123.3(4) . . ?
C15 C14 N1 118.2(4) . . ?
C14 C15 H15 122.0 . . ?
C14 C15 C16 116.0(4) . . ?
C16 C15 H15 122.0 . . ?
C15 C16 N2 117.5(4) . . ?
C17 C16 N2 118.9(4) . . ?
C17 C16 C15 123.6(4) . . ?
C12 C17 H17 121.1 . . ?
C16 C17 C12 117.9(4) . . ?
C16 C17 H17 121.1 . . ?

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 C3 C4 C5 -129.1(3) . . . . ?
O1 C3 C4 C6 106.5(4) . . . . ?
O2 C2 C3 O1 -11.0(4) . . . . ?
O2 C2 C3 C4 -128.6(3) . . . . ?
O3 C1 C2 O2 35.4(5) . . . . ?
O3 C1 C2 C3 -79.8(4) . . . . ?
O3 C1 C5 F1 -172.0(3) . . . . ?
O3 C1 C5 C4 72.5(4) . . . . ?
O3 C11 C12 C13 -2.3(5) . . . . ?
O3 C11 C12 C17 177.1(3) . . . . ?
O4 C11 C12 C13 -179.4(4) . . . . ?
O4 C11 C12 C17 0.0(6) . . . . ?
O5 N1 C14 C13 9.0(5) . . . . ?
O5 N1 C14 C15 -171.4(4) . . . . ?
O6 N1 C14 C13 -171.0(4) . . . . ?
O6 N1 C14 C15 8.6(5) . . . . ?
O7 N2 C16 C15 0.1(5) . . . . ?
O7 N2 C16 C17 178.9(3) . . . . ?
O8 N2 C16 C15 -179.6(4) . . . . ?
O8 N2 C16 C17 -0.9(5) . . . . ?
N1 C14 C15 C16 -179.6(3) . . . . ?
N2 C16 C17 C12 -177.8(3) . . . . ?
C1 O3 C11 O4 -7.9(6) . . . . ?
C1 O3 C11 C12 175.0(3) . . . . ?
C1 C2 C3 O1 109.4(3) . . . . ?
C1 C2 C3 C4 -8.2(4) . . . . ?
C2 O2 C8 O1 30.2(4) . . . . ?
C2 O2 C8 C9 146.3(3) . . . . ?
C2 O2 C8 C10 -89.5(4) . . . . ?
C2 C1 C5 F1 74.3(4) . . . . ?
C2 C1 C5 C4 -41.1(4) . . . . ?
C2 C3 C4 C5 -16.8(4) . . . . ?
C2 C3 C4 C6 -141.2(4) . . . . ?
C3 O1 C8 O2 -37.6(4) . . . . ?
C3 O1 C8 C9 -152.9(3) . . . . ?
C3 O1 C8 C10 80.8(4) . . . . ?
C3 C4 C5 F1 -76.8(4) . . . . ?
C3 C4 C5 C1 35.9(4) . . . . ?
C3 C4 C6 C7 -129.0(5) . . . . ?
C5 C1 C2 O2 145.1(3) . . . . ?
C5 C1 C2 C3 29.9(4) . . . . ?
C5 C4 C6 C7 111.7(5) . . . . ?
C6 C4 C5 F1 49.4(5) . . . . ?
C6 C4 C5 C1 162.1(3) . . . . ?
C8 O1 C3 C2 29.7(4) . . . . ?
C8 O1 C3 C4 144.4(3) . . . . ?
C8 O2 C2 C1 -126.6(4) . . . . ?
C8 O2 C2 C3 -11.6(4) . . . . ?
C11 O3 C1 C2 -93.0(4) . . . . ?
C11 O3 C1 C5 158.1(3) . . . . ?
C11 C12 C13 C14 179.5(4) . . . . ?
C11 C12 C17 C16 -180.0(4) . . . . ?
C12 C13 C14 N1 179.8(3) . . . . ?
C12 C13 C14 C15 0.2(6) . . . . ?
C13 C12 C17 C16 -0.6(5) . . . . ?
C13 C14 C15 C16 -0.1(6) . . . . ?
C14 C15 C16 N2 178.2(4) . . . . ?
C14 C15 C16 C17 -0.5(6) . . . . ?
C15 C16 C17 C12 0.8(6) . . . . ?
C17 C12 C13 C14 0.1(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_16
_database_code_depnum_ccdc_archive 'CCDC 2193043'
loop_
_audit_author_name
_audit_author_address
'Valentyna D. Slyusarchuk'
;Keele University
United Kingdom
;
_audit_update_record             
;
2022-07-27 deposited with the CCDC.	2022-11-14 downloaded from the CCDC.
;
_audit_creation_date             2022-07-19
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C9 H14 F2 O4'
_chemical_formula_sum            'C9 H14 F2 O4'
_chemical_formula_weight         224.20
_chemical_absolute_configuration syn
_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      trigonal
_space_group_IT_number           145
_space_group_name_H-M_alt        'P 32'
_space_group_name_Hall           'P 32'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z+2/3'
'-x+y, -x, z+1/3'

_cell_length_a                   12.3659(5)
_cell_length_b                   12.3659(5)
_cell_length_c                   5.8839(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     779.20(8)
_cell_formula_units_Z            3
_cell_measurement_reflns_used    4123
_cell_measurement_temperature    150.0
_cell_measurement_theta_max      27.44
_cell_measurement_theta_min      3.295
_shelx_estimated_absorpt_T_max   0.988
_shelx_estimated_absorpt_T_min   0.959
_exptl_absorpt_coefficient_mu    0.133
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6801
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0533 before and 0.0490 after correction.
The Ratio of minimum to maximum transmission is 0.9122.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.433
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             354
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.09
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0334
_diffrn_reflns_av_unetI/netI     0.0301
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            9224
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.476
_diffrn_reflns_theta_min         3.295
_diffrn_ambient_temperature      150.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_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           20.0
_diffrn_source_power             1.0
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.999
_reflns_Friedel_fraction_full    0.996
_reflns_Friedel_fraction_max     0.997
_reflns_number_gt                2110
_reflns_number_total             2375
_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       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.143
_refine_diff_density_min         -0.159
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details 
;
 Flack x determined using 928 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.2(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     144
_refine_ls_number_reflns         2375
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0391
_refine_ls_R_factor_gt           0.0319
_refine_ls_restrained_S_all      1.041
_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)+(0.0359P)²+0.0750P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0680
_refine_ls_wR_factor_ref         0.0714
_refine_special_details          ?
_olex2_refinement_description    
;
1. Others
 Fixed Uiso: H2(0.025) H3(0.026) H4A(0.027) H5(0.024) H6A(0.027) H6B(0.027)
 H9A(0.061) H9B(0.061) H9C(0.061) H1(0.061) H4(0.061) H8A(0.069) H8B(0.069)
 H8C(0.069)
 Fixed X: H2(0.4707) H3(0.6524) H4A(0.5232) H5(0.4245) H6A(0.3105) H6B(0.233)
 H9A(0.9218) H9B(0.8592) H9C(0.8324) H8A(0.6806) H8B(0.7747) H8C(0.8264)
 Fixed Y: H2(0.3336) H3(0.5086) H4A(0.5909) H5(0.5747) H6A(0.4148) H6B(0.4161)
 H9A(0.7897) H9B(0.8678) H9C(0.7427) H8A(0.707) H8B(0.8445) H8C(0.7536)
 Fixed Z: H2(0.2948) H3(0.1823) H4A(0.1483) H5(0.5733) H6A(0.1858) H6B(0.4032)
 H9A(0.4085) H9B(0.3189) H9C(0.1907) H8A(0.8182) H8B(0.7262) H8C(0.7961)
;
_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 0.32210(15) 0.30649(14) 0.6017(3) 0.0373(4) Uani 1 1 d . . . . .
F2 F 0.48324(15) 0.44699(15) 0.7857(2) 0.0323(4) Uani 1 1 d . . . . .
O1 O 0.57156(17) 0.32138(15) 0.5371(3) 0.0250(4) Uani 1 1 d D . . . .
O2 O 0.70645(16) 0.58173(15) 0.4993(3) 0.0242(4) Uani 1 1 d . . . . .
O3 O 0.62909(16) 0.70634(16) 0.3940(4) 0.0407(5) Uani 1 1 d . . . . .
O4 O 0.29875(16) 0.56882(16) 0.2128(3) 0.0240(4) Uani 1 1 d D . . . .
C1 C 0.5212(2) 0.3865(2) 0.4255(4) 0.0208(5) Uani 1 1 d . . . . .
H2 H 0.4707 0.3336 0.2948 0.025 Uiso 1 1 calc R U . . .
C2 C 0.6151(2) 0.5140(2) 0.3297(4) 0.0213(5) Uani 1 1 d . . . . .
H3 H 0.6524 0.5086 0.1823 0.026 Uiso 1 1 calc R U . . .
C3 C 0.5447(2) 0.5862(2) 0.3105(4) 0.0221(5) Uani 1 1 d . . . . .
H4A H 0.5232 0.5909 0.1483 0.027 Uiso 1 1 calc R U . . .
C4 C 0.4249(2) 0.5167(2) 0.4552(4) 0.0199(4) Uani 1 1 d . . . . .
H5 H 0.4245 0.5747 0.5733 0.024 Uiso 1 1 calc R U . . .
C5 C 0.3077(2) 0.4680(2) 0.3090(4) 0.0225(5) Uani 1 1 d . . . . .
H6A H 0.3105 0.4148 0.1858 0.027 Uiso 1 1 calc R U . . .
H6B H 0.2330 0.4161 0.4032 0.027 Uiso 1 1 calc R U . . .
C6 C 0.4353(2) 0.4124(2) 0.5705(4) 0.0227(5) Uani 1 1 d . . . . .
C7 C 0.7359(2) 0.7086(2) 0.4909(4) 0.0244(5) Uani 1 1 d . . . . .
C8 C 0.8471(3) 0.7838(3) 0.3389(5) 0.0409(7) Uani 1 1 d . . . . .
H9A H 0.9218 0.7897 0.4085 0.061 Uiso 1 1 calc R U . . .
H9B H 0.8592 0.8678 0.3189 0.061 Uiso 1 1 calc R U . . .
H9C H 0.8324 0.7427 0.1907 0.061 Uiso 1 1 calc R U . . .
H1 H 0.620(3) 0.369(3) 0.642(6) 0.061 Uiso 1 1 d D U . . .
H4 H 0.287(4) 0.608(3) 0.314(5) 0.061 Uiso 1 1 d D U . . .
C9 C 0.7561(3) 0.7576(3) 0.7282(6) 0.0459(7) Uani 1 1 d . . . . .
H8A H 0.6806 0.7070 0.8182 0.069 Uiso 1 1 calc R U . . .
H8B H 0.7747 0.8445 0.7262 0.069 Uiso 1 1 calc R U . . .
H8C H 0.8264 0.7536 0.7961 0.069 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 C6 1.370(3) . ?
F2 C6 1.373(3) . ?
O1 C1 1.402(3) . ?
O1 H1 0.86(3) . ?
O2 C2 1.424(3) . ?
O2 C7 1.423(3) . ?
O3 C3 1.410(3) . ?
O3 C7 1.426(3) . ?
O4 C5 1.423(3) . ?
O4 H4 0.83(2) . ?
C1 H2 1.0000 . ?
C1 C2 1.523(3) . ?
C2 H3 1.0000 . ?
C2 C3 1.532(3) . ?
C3 H4A 1.0000 . ?
C3 C4 1.544(3) . ?
C4 H5 1.0000 . ?
C4 C5 1.526(3) . ?
C5 H6A 0.9900 . ?
C5 H6B 0.9900 . ?
C6 C1 1.517(3) . ?
C6 C4 1.519(3) . ?
C7 C8 1.508(4) . ?
C7 C9 1.492(4) . ?
C8 H9A 0.9800 . ?
C8 H9B 0.9800 . ?
C8 H9C 0.9800 . ?
C9 H8A 0.9800 . ?
C9 H8B 0.9800 . ?
C9 H8C 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 O1 H1 107(3) . . ?
C7 O2 C2 108.37(17) . . ?
C3 O3 C7 110.54(17) . . ?
C5 O4 H4 110(3) . . ?
O1 C1 H2 107.2 . . ?
O1 C1 C2 116.1(2) . . ?
O1 C1 C6 114.64(19) . . ?
C2 C1 H2 107.2 . . ?
C6 C1 H2 107.2 . . ?
C6 C1 C2 103.91(17) . . ?
O2 C2 C1 108.65(18) . . ?
O2 C2 H3 112.9 . . ?
O2 C2 C3 102.95(18) . . ?
C1 C2 H3 112.9 . . ?
C1 C2 C3 105.67(18) . . ?
C3 C2 H3 112.9 . . ?
O3 C3 C2 104.56(18) . . ?
O3 C3 H4A 110.5 . . ?
O3 C3 C4 113.1(2) . . ?
C2 C3 H4A 110.5 . . ?
C2 C3 C4 107.57(19) . . ?
C4 C3 H4A 110.5 . . ?
C3 C4 H5 109.4 . . ?
C5 C4 C3 111.46(19) . . ?
C5 C4 H5 109.4 . . ?
C6 C4 C3 104.67(18) . . ?
C6 C4 H5 109.4 . . ?
C6 C4 C5 112.52(19) . . ?
O4 C5 C4 110.62(19) . . ?
O4 C5 H6A 109.5 . . ?
O4 C5 H6B 109.5 . . ?
C4 C5 H6A 109.5 . . ?
C4 C5 H6B 109.5 . . ?
H6A C5 H6B 108.1 . . ?
F1 C6 F2 104.46(18) . . ?
F1 C6 C1 111.23(19) . . ?
F1 C6 C4 113.1(2) . . ?
F2 C6 C1 110.2(2) . . ?
F2 C6 C4 110.75(19) . . ?
C1 C6 C4 107.14(18) . . ?
O2 C7 O3 105.53(18) . . ?
O2 C7 C8 110.6(2) . . ?
O2 C7 C9 108.3(2) . . ?
O3 C7 C8 109.0(2) . . ?
O3 C7 C9 110.3(2) . . ?
C9 C7 C8 112.9(2) . . ?
C7 C8 H9A 109.5 . . ?
C7 C8 H9B 109.5 . . ?
C7 C8 H9C 109.5 . . ?
H9A C8 H9B 109.5 . . ?
H9A C8 H9C 109.5 . . ?
H9B C8 H9C 109.5 . . ?
C7 C9 H8A 109.5 . . ?
C7 C9 H8B 109.5 . . ?
C7 C9 H8C 109.5 . . ?
H8A C9 H8B 109.5 . . ?
H8A C9 H8C 109.5 . . ?
H8B C9 H8C 109.5 . . ?

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
O1 H1 O1 0.86(3) 1.94(3) 2.746(2) 157(4) 3_665
O4 H4 O4 0.83(2) 1.86(2) 2.690(2) 177(4) 3_565

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 C6 C1 O1 -74.4(3) . . . . ?
F1 C6 C1 C2 157.85(18) . . . . ?
F1 C6 C4 C3 -146.7(2) . . . . ?
F1 C6 C4 C5 -25.5(3) . . . . ?
F2 C6 C1 O1 41.0(3) . . . . ?
F2 C6 C1 C2 -86.8(2) . . . . ?
F2 C6 C4 C3 96.4(2) . . . . ?
F2 C6 C4 C5 -142.40(19) . . . . ?
O1 C1 C2 O2 -47.0(2) . . . . ?
O1 C1 C2 C3 -156.86(19) . . . . ?
O2 C2 C3 O3 22.4(2) . . . . ?
O2 C2 C3 C4 -98.2(2) . . . . ?
O3 C3 C4 C5 127.9(2) . . . . ?
O3 C3 C4 C6 -110.2(2) . . . . ?
C1 C2 C3 O3 136.3(2) . . . . ?
C1 C2 C3 C4 15.8(2) . . . . ?
C1 C6 C4 C3 -23.8(2) . . . . ?
C1 C6 C4 C5 97.4(2) . . . . ?
C2 O2 C7 O3 24.6(2) . . . . ?
C2 O2 C7 C8 -93.0(2) . . . . ?
C2 O2 C7 C9 142.8(2) . . . . ?
C2 C3 C4 C5 -117.1(2) . . . . ?
C2 C3 C4 C6 4.7(2) . . . . ?
C3 O3 C7 O2 -9.3(3) . . . . ?
C3 O3 C7 C8 109.5(2) . . . . ?
C3 O3 C7 C9 -126.1(2) . . . . ?
C3 C4 C5 O4 -65.4(2) . . . . ?
C4 C6 C1 O1 161.56(19) . . . . ?
C4 C6 C1 C2 33.8(2) . . . . ?
C6 C1 C2 O2 79.9(2) . . . . ?
C6 C1 C2 C3 -30.0(2) . . . . ?
C6 C4 C5 O4 177.32(19) . . . . ?
C7 O2 C2 C1 -140.71(18) . . . . ?
C7 O2 C2 C3 -29.0(2) . . . . ?
C7 O3 C3 C2 -8.2(3) . . . . ?
C7 O3 C3 C4 108.6(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_11
_database_code_depnum_ccdc_archive 'CCDC 2193042'
loop_
_audit_author_name
_audit_author_address
'Valentyna D. Slyusarchuk'
;Keele University
United Kingdom
;
_audit_update_record             
;
2022-07-27 deposited with the CCDC.	2022-11-14 downloaded from the CCDC.
;
_audit_creation_date             2022-07-19
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C10 H15 F O3'
_chemical_formula_sum            'C10 H15 F O3'
_chemical_formula_weight         202.22
_chemical_absolute_configuration syn
_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           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   7.6334(3)
_cell_length_b                   5.7702(2)
_cell_length_c                   11.1406(5)
_cell_angle_alpha                90
_cell_angle_beta                 100.4260(10)
_cell_angle_gamma                90
_cell_volume                     482.60(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    6119
_cell_measurement_temperature    150.0
_cell_measurement_theta_max      30.518
_cell_measurement_theta_min      2.713
_shelx_estimated_absorpt_T_max   0.992
_shelx_estimated_absorpt_T_min   0.981
_exptl_absorpt_coefficient_mu    0.113
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6754
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0601 before and 0.0538 after correction.
The Ratio of minimum to maximum transmission is 0.9052.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.392
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             216
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.07
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0424
_diffrn_reflns_av_unetI/netI     0.0376
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            15047
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.550
_diffrn_reflns_theta_min         2.999
_diffrn_ambient_temperature      150.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_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                   ?
_reflns_Friedel_coverage         0.830
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.987
_reflns_number_gt                2591
_reflns_number_total             2937
_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       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.282
_refine_diff_density_min         -0.200
_refine_diff_density_rms         0.044
_refine_ls_abs_structure_details 
;
 Flack x determined using 1033 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.1(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     132
_refine_ls_number_reflns         2937
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0487
_refine_ls_R_factor_gt           0.0394
_refine_ls_restrained_S_all      1.057
_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)+(0.0439P)²+0.0541P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0832
_refine_ls_wR_factor_ref         0.0871
_refine_special_details          ?
_olex2_refinement_description    
;
1. Restrained distances
 O1-H1
 0.95 with sigma of 0.02
2.a Ternary CH refined with riding coordinates:
 C1(H1A), C2(H2), C3(H3), C4(H4), C7(H7)
2.b Aromatic/amide H refined with riding coordinates:
 C5(H5)
2.c X=CH2 refined with riding coordinates:
 C6(H6A,H6B)
2.d Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C10(H10A,H10B,H10C)
;
_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
F1 F 0.80656(16) 0.1804(2) 0.53821(11) 0.0217(3) Uani 1 1 d . . . . .
O1 O 0.70697(19) 0.5978(3) 0.42919(12) 0.0188(3) Uani 1 1 d D . . . .
O2 O 0.54803(19) 0.7529(2) 0.68121(12) 0.0153(3) Uani 1 1 d . . . . .
O3 O 0.62664(19) 0.5013(2) 0.83702(12) 0.0183(3) Uani 1 1 d . . . . .
C1 C 0.7536(2) 0.5822(4) 0.55750(16) 0.0147(3) Uani 1 1 d . . . . .
H1A H 0.814940 0.729358 0.588331 0.018 Uiso 1 1 calc R U . . .
C2 C 0.5958(2) 0.5456(3) 0.62401(16) 0.0136(4) Uani 1 1 d . . . . .
H2 H 0.490866 0.478101 0.568155 0.016 Uiso 1 1 calc R U . . .
C3 C 0.6627(2) 0.3823(3) 0.73190(16) 0.0142(3) Uani 1 1 d . . . . .
H3 H 0.599580 0.229744 0.721217 0.017 Uiso 1 1 calc R U . . .
C4 C 0.8639(2) 0.3524(3) 0.73585(17) 0.0157(4) Uani 1 1 d . . . . .
H4 H 0.927016 0.485350 0.782485 0.019 Uiso 1 1 calc R U . . .
C5 C 0.9403(3) 0.1321(4) 0.79414(19) 0.0212(4) Uani 1 1 d . . . . .
H5 H 0.901891 -0.009135 0.754077 0.025 Uiso 1 1 calc R U . . .
C6 C 1.0567(3) 0.1193(4) 0.8967(2) 0.0262(5) Uani 1 1 d . . . . .
H6A H 1.098389 0.256770 0.939429 0.031 Uiso 1 1 calc R U . . .
H6B H 1.099087 -0.027517 0.927952 0.031 Uiso 1 1 calc R U . . .
C7 C 0.8779(3) 0.3810(4) 0.60179(17) 0.0165(4) Uani 1 1 d . . . . .
H7 H 1.002956 0.412169 0.590872 0.020 Uiso 1 1 calc R U . . .
C8 C 0.5004(3) 0.6783(3) 0.79480(17) 0.0156(4) Uani 1 1 d . . . . .
C9 C 0.3121(3) 0.5840(4) 0.77248(19) 0.0207(4) Uani 1 1 d . . . . .
H9A H 0.303307 0.454040 0.715073 0.031 Uiso 1 1 calc R U . . .
H9B H 0.229005 0.706430 0.738096 0.031 Uiso 1 1 calc R U . . .
H9C H 0.282297 0.530561 0.849813 0.031 Uiso 1 1 calc R U . . .
C10 C 0.5257(3) 0.8773(4) 0.88349(18) 0.0197(4) Uani 1 1 d . . . . .
H10A H 0.500963 0.825241 0.962477 0.030 Uiso 1 1 calc R U . . .
H10B H 0.443935 1.003110 0.852106 0.030 Uiso 1 1 calc R U . . .
H10C H 0.648793 0.933064 0.893673 0.030 Uiso 1 1 calc R U . . .
H1 H 0.641(3) 0.477(4) 0.404(2) 0.030 Uiso 1 1 d D 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 C7 1.414(2) . ?
O1 C1 1.412(2) . ?
O1 H1 0.88(2) . ?
O2 C2 1.433(2) . ?
O2 C8 1.444(2) . ?
O3 C3 1.427(2) . ?
O3 C8 1.424(2) . ?
C1 H1A 1.0000 . ?
C1 C2 1.539(2) . ?
C1 C7 1.524(3) . ?
C2 H2 1.0000 . ?
C2 C3 1.540(3) . ?
C3 H3 1.0000 . ?
C3 C4 1.539(3) . ?
C4 H4 1.0000 . ?
C4 C5 1.496(3) . ?
C4 C7 1.525(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.316(3) . ?
C6 H6A 0.9500 . ?
C6 H6B 0.9500 . ?
C7 H7 1.0000 . ?
C8 C9 1.515(3) . ?
C8 C10 1.504(3) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 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 O1 H1 107.1(18) . . ?
C2 O2 C8 105.41(13) . . ?
C8 O3 C3 107.07(14) . . ?
O1 C1 H1A 108.1 . . ?
O1 C1 C2 114.86(15) . . ?
O1 C1 C7 113.85(16) . . ?
C2 C1 H1A 108.1 . . ?
C7 C1 H1A 108.1 . . ?
C7 C1 C2 103.62(15) . . ?
O2 C2 C1 112.57(14) . . ?
O2 C2 H2 111.2 . . ?
O2 C2 C3 103.81(14) . . ?
C1 C2 H2 111.2 . . ?
C1 C2 C3 106.38(15) . . ?
C3 C2 H2 111.2 . . ?
O3 C3 C2 105.08(15) . . ?
O3 C3 H3 111.2 . . ?
O3 C3 C4 111.73(15) . . ?
C2 C3 H3 111.2 . . ?
C4 C3 C2 106.21(15) . . ?
C4 C3 H3 111.2 . . ?
C3 C4 H4 108.2 . . ?
C5 C4 C3 114.60(16) . . ?
C5 C4 H4 108.2 . . ?
C5 C4 C7 115.22(17) . . ?
C7 C4 C3 101.90(14) . . ?
C7 C4 H4 108.2 . . ?
C4 C5 H5 117.5 . . ?
C6 C5 C4 125.0(2) . . ?
C6 C5 H5 117.5 . . ?
C5 C6 H6A 120.0 . . ?
C5 C6 H6B 120.0 . . ?
H6A C6 H6B 120.0 . . ?
F1 C7 C1 107.50(14) . . ?
F1 C7 C4 108.23(16) . . ?
F1 C7 H7 112.1 . . ?
C1 C7 C4 104.46(15) . . ?
C1 C7 H7 112.1 . . ?
C4 C7 H7 112.1 . . ?
O2 C8 C9 110.18(15) . . ?
O2 C8 C10 109.00(16) . . ?
O3 C8 O2 103.91(14) . . ?
O3 C8 C9 111.20(17) . . ?
O3 C8 C10 109.36(16) . . ?
C10 C8 C9 112.79(17) . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C8 C10 H10A 109.5 . . ?
C8 C10 H10B 109.5 . . ?
C8 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?

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
O1 H1 O2 0.88(2) 2.04(2) 2.898(2) 166(3) 2_646 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 C1 C2 O2 -103.65(19) . . . . ?
O1 C1 C2 C3 143.29(17) . . . . ?
O1 C1 C7 F1 -48.3(2) . . . . ?
O1 C1 C7 C4 -163.15(15) . . . . ?
O2 C2 C3 O3 6.67(18) . . . . ?
O2 C2 C3 C4 -111.87(16) . . . . ?
O3 C3 C4 C5 91.1(2) . . . . ?
O3 C3 C4 C7 -143.76(16) . . . . ?
C1 C2 C3 O3 125.64(15) . . . . ?
C1 C2 C3 C4 7.10(19) . . . . ?
C2 O2 C8 O3 39.04(17) . . . . ?
C2 O2 C8 C9 -80.18(18) . . . . ?
C2 O2 C8 C10 155.56(15) . . . . ?
C2 C1 C7 F1 77.15(17) . . . . ?
C2 C1 C7 C4 -37.69(18) . . . . ?
C2 C3 C4 C5 -154.84(16) . . . . ?
C2 C3 C4 C7 -29.71(19) . . . . ?
C3 O3 C8 O2 -34.69(18) . . . . ?
C3 O3 C8 C9 83.82(18) . . . . ?
C3 O3 C8 C10 -150.95(16) . . . . ?
C3 C4 C5 C6 -114.3(2) . . . . ?
C3 C4 C7 F1 -72.52(18) . . . . ?
C3 C4 C7 C1 41.80(18) . . . . ?
C5 C4 C7 F1 52.2(2) . . . . ?
C5 C4 C7 C1 166.52(16) . . . . ?
C7 C1 C2 O2 131.54(15) . . . . ?
C7 C1 C2 C3 18.47(18) . . . . ?
C7 C4 C5 C6 127.9(2) . . . . ?
C8 O2 C2 C1 -142.27(15) . . . . ?
C8 O2 C2 C3 -27.64(17) . . . . ?
C8 O3 C3 C2 17.19(19) . . . . ?
C8 O3 C3 C4 131.94(16) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
