# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2024

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

data_svh21023
_database_code_depnum_ccdc_archive 'CCDC 2306049'
_audit_update_record             
;
2023-11-06 deposited with the CCDC.	2023-12-08 downloaded from the CCDC.
;
_audit_creation_date             2023-11-06
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
shyamkumar.vadakket-haridas@uni-ulm.de
_publ_section_exptl              
;
Any special experimental details
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C9 H15 F3 O3'
_chemical_formula_sum            'C9 H15 F3 O3'
_chemical_formula_weight         228.21
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C9 H15 O3 F3'
_chemical_oxdiff_usercomment     SVH-116
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      hexagonal
_space_group_IT_number           173
_space_group_name_H-M_alt        'P 63'
_space_group_name_Hall           'P 6c'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'-x, -y, z+1/2'
'y, -x+y, z+1/2'
'x-y, x, z+1/2'

_cell_length_a                   11.4469(4)
_cell_length_b                   11.4469(4)
_cell_length_c                   4.7028(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     533.66(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1694
_cell_measurement_temperature    150.00
_cell_measurement_theta_max      72.6630
_cell_measurement_theta_min      4.4400
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.209
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.708
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.82a (Rigaku Oxford Diffraction, 2020)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_lustre     ?
_exptl_crystal_colour_modifier   ?
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.420
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             240
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-7 1 0 0.0328
-2 0 -3 0.1991
0 1 3 0.2560
-3 7 0 0.0362
3 -7 0 0.0378
-3 7 0 0.0526
2 5 0 0.0426
7 -1 0 0.0476
6 -7 0 0.0329
-6 7 0 0.0482
-1 -6 -1 0.0798
-7 4 0 0.0393

_exptl_crystal_preparation       
'Crystallized by slow evaporation from Acetone  solution.'
_exptl_crystal_recrystallization_method 
'Crystallized by slow evaporation from  Acetone solution.'
_exptl_crystal_size_max          0.488
_exptl_crystal_size_mid          0.097
_exptl_crystal_size_min          0.074
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-6.9448 1.1874 -0.0619 0.9025 -0.4288 -0.0409
-2.0654 -0.0858 -2.8840 0.3406 -0.1653 0.9256
-0.3089 0.5196 3.0448 -0.0367 0.0211 -0.9991
-3.3657 7.4190 0.0333 0.5194 0.8506 -0.0815
3.3645 -7.4192 -0.0214 -0.5196 -0.8509 0.0776
-3.2811 7.3415 -0.4319 0.5203 0.8510 0.0715
1.9559 5.2302 -0.0775 -0.1835 0.9830 0.0092
6.9505 -1.2022 -0.0514 -0.9003 0.4283 0.0780
6.2204 -6.6239 -0.0633 -0.8732 -0.4752 0.1087
-6.1997 6.5939 0.2798 0.8643 0.4701 -0.1790
-0.9157 -5.6067 -0.9520 0.0740 -0.9385 0.3371
-7.3875 4.0354 -0.2778 0.9996 -0.0249 0.0091

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0353
_diffrn_reflns_av_unetI/netI     0.0196
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       3
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_number            3334
_diffrn_reflns_point_group_measured_fraction_full 0.787
_diffrn_reflns_point_group_measured_fraction_max 0.764
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.859
_diffrn_reflns_theta_min         4.460
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3385
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -115.00 -40.00   1.00    1.00    --  -43.06 -38.00-120.00   75
  2  ω   -119.00 -14.00   1.00    1.00    --  -43.06 -19.00 120.00  105
  3  ω    -60.00 -14.00   1.00    1.00    --  -43.06 125.00  30.00   46
  4  ω     27.00  96.00   1.00    1.00    --   43.06-125.00  30.00   69
  5  ω     33.00  67.00   1.00    1.54    --  104.94-125.00 -30.00   34
  6  ω     69.00 111.00   1.00    1.54    --  104.94-125.00 -30.00   42
  7  ω     58.00 128.00   1.00    1.54    --  104.94 -77.00 120.00   70
  8  ω    103.00 172.00   1.00    1.54    --  104.94  77.00 -60.00   69
  9  ω    100.00 151.00   1.00    1.54    --  104.94 125.00-120.00   51
 10  ω     32.00 129.00   1.00    1.54    --  104.94 -45.00 -90.00   97
 11  ω     31.00 103.00   1.00    1.54    --  104.94 -95.00  90.00   72
 12  ω     41.00  67.00   1.00    1.54    --  104.94 -45.00 150.00   26
 13  ω     74.00 107.00   1.00    1.54    --  104.94 -45.00 150.00   33
 14  ω     49.00 177.00   1.00    1.54    --  104.94   0.00 -90.00  128
 15  ω     78.00 122.00   1.00    1.54    --  104.94 -77.00 -60.00   44
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova Oxford instruments/Rigaku'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1276120000
_diffrn_orient_matrix_UB_12      0.0122394000
_diffrn_orient_matrix_UB_13      -0.0270770000
_diffrn_orient_matrix_UB_21      0.0883057000
_diffrn_orient_matrix_UB_22      0.1547635000
_diffrn_orient_matrix_UB_23      -0.0105360000
_diffrn_orient_matrix_UB_31      0.0077729000
_diffrn_orient_matrix_UB_32      -0.0059896000
_diffrn_orient_matrix_UB_33      -0.3263232000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.367
_reflns_Friedel_fraction_full    0.509
_reflns_Friedel_fraction_max     0.470
_reflns_number_gt                509
_reflns_number_total             548
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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       'CrysAlisPro 1.171.40.82a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.82a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.82a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.173
_refine_diff_density_min         -0.138
_refine_diff_density_rms         0.034
_refine_ls_abs_structure_details 
;
 Flack x determined using 136 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.38(18)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.105
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     47
_refine_ls_number_reflns         548
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0306
_refine_ls_R_factor_gt           0.0270
_refine_ls_restrained_S_all      1.103
_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)+(0.0363P)²+0.0934P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0697
_refine_ls_wR_factor_ref         0.0726
_refine_special_details          ?
_olex2_refinement_description    
;
1.a Ternary CH refined with riding coordinates:
 C003(H003), C004(H004)
1.b Idealised Me refined as rotating group:
 C005(H00A,H00B,H00C)
;
_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
F001 F 0.41903(11) 0.58607(10) 0.2937(3) 0.0297(3) Uani 1 1 d . . . . .
O002 O 0.61354(14) 0.80556(13) 0.5783(4) 0.0328(4) Uani 1 1 d . . . . .
C003 C 0.47976(17) 0.74255(17) 0.6824(6) 0.0255(4) Uani 1 1 d . . . . .
H003 H 0.483966 0.744666 0.890549 0.031 Uiso 1 1 calc R U . . .
C004 C 0.41073(19) 0.59541(19) 0.5894(5) 0.0247(5) Uani 1 1 d . . . . .
H004 H 0.456965 0.552571 0.679728 0.030 Uiso 1 1 calc R U . . .
C005 C 0.7001(2) 0.9318(2) 0.7081(7) 0.0429(6) Uani 1 1 d . . . . .
H00A H 0.678561 0.997771 0.639321 0.064 Uiso 1 1 calc R U . . .
H00B H 0.792094 0.959670 0.662232 0.064 Uiso 1 1 calc R U . . .
H00C H 0.688190 0.923434 0.910599 0.064 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F001 C004 1.402(3) . ?
O002 C003 1.414(2) . ?
O002 C005 1.418(3) . ?
C003 H003 0.9800 . ?
C003 C004 1.524(3) . ?
C003 C004 1.530(3) 2_665 ?
C004 H004 0.9800 . ?
C005 H00A 0.9600 . ?
C005 H00B 0.9600 . ?
C005 H00C 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
C003 O002 C005 113.42(18) . . ?
O002 C003 H003 107.8 . . ?
O002 C003 C004 112.57(18) . 2_665 ?
O002 C003 C004 107.18(17) . . ?
C004 C003 H003 107.8 2_665 . ?
C004 C003 H003 107.8 . . ?
C004 C003 C004 113.4(2) . 2_665 ?
F001 C004 C003 109.78(19) . 3_565 ?
F001 C004 C003 110.58(19) . . ?
F001 C004 H004 108.5 . . ?
C003 C004 C003 110.9(2) . 3_565 ?
C003 C004 H004 108.5 . . ?
C003 C004 H004 108.5 3_565 . ?
O002 C005 H00A 109.5 . . ?
O002 C005 H00B 109.5 . . ?
O002 C005 H00C 109.5 . . ?
H00A C005 H00B 109.5 . . ?
H00A C005 H00C 109.5 . . ?
H00B C005 H00C 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
O002 C003 C004 F001 -55.6(2) . . . . ?
O002 C003 C004 C003 -177.59(14) . . . 3_565 ?
C004 C003 C004 F001 69.3(3) 2_665 . . . ?
C004 C003 C004 C003 -52.7(4) 2_665 . . 3_565 ?
C005 O002 C003 C004 -164.4(2) . . . . ?
C005 O002 C003 C004 70.1(3) . . . 2_665 ?


_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.152
_oxdiff_exptl_absorpt_empirical_full_min 0.585
####################################################################### 
# 
# 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_svh21049
_database_code_depnum_ccdc_archive 'CCDC 2306050'
_audit_update_record             
;
2023-11-06 deposited with the CCDC.	2023-12-08 downloaded from the CCDC.
;
_audit_creation_date             2023-11-06
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
shyamkumar.vadakket-haridas@uni-ulm.de
_publ_section_exptl              
;
Any special experimental details
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C6 H11 F3 O4'
_chemical_formula_sum            'C6 H11 F3 O4'
_chemical_formula_weight         204.15
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C6 H9 O3 F3'
_chemical_oxdiff_usercomment     SVH-120-MeOH/Acetone
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           62
_space_group_name_H-M_alt        'P n m a'
_space_group_name_Hall           '-P 2ac 2n'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z'
'x+1/2, -y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z'
'-x-1/2, y-1/2, z-1/2'

_cell_length_a                   17.1696(5)
_cell_length_b                   9.4705(3)
_cell_length_c                   4.82980(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     785.35(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2596
_cell_measurement_temperature    149.95(10)
_cell_measurement_theta_max      72.7800
_cell_measurement_theta_min      5.1490
_shelx_estimated_absorpt_T_max   0.865
_shelx_estimated_absorpt_T_min   0.480
_exptl_absorpt_coefficient_mu    1.659
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.611
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.82a (Rigaku Oxford Diffraction, 2020)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.727
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             424
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-7 -5 0 0.0529
7 5 0 0.0752
3 -1 3 0.2445
-3 1 -3 0.2425
-8 4 0 0.0592
7 -5 0 0.0281
0 1 3 0.2478
-5 2 -3 0.2026
-10 -3 0 0.0521
-7 4 1 0.1283
-9 4 0 0.0526
-1 -2 -3 0.2369
7 4 -1 0.1338

_exptl_crystal_preparation       'Recrystallized from Acetone'
_exptl_crystal_recrystallization_method 'Recrystallized from Acetone'
_exptl_crystal_size_max          0.519
_exptl_crystal_size_mid          0.141
_exptl_crystal_size_min          0.09
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-6.6267 -4.9138 0.2863 -0.2659 -0.0464 0.9629
6.8581 4.8482 -0.0297 0.1845 0.0311 -0.9823
2.8828 -0.6505 3.0092 -0.9510 -0.1784 -0.2525
-2.6634 0.8101 -3.0152 0.9586 0.1797 0.2208
-7.6457 4.4699 -0.0607 0.4760 -0.8746 -0.0922
7.3712 -4.6090 0.0420 -0.4741 0.8714 0.1260
-0.1830 1.1496 3.0788 -0.7861 -0.5429 -0.2955
-4.7053 2.1768 -2.6150 0.9801 -0.1272 0.1526
-9.9167 -2.8077 -0.0171 0.0290 -0.3997 0.9162
-6.9108 4.1805 1.2260 0.0792 -0.9823 -0.1699
-8.9574 3.6400 0.1741 0.3827 -0.9211 0.0715
-1.4046 -2.0234 -2.9332 0.7208 0.4948 0.4853
7.4418 3.9950 -1.1419 0.4284 0.2987 -0.8528

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0396
_diffrn_reflns_av_unetI/netI     0.0212
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       5
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_number            4748
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.044
_diffrn_reflns_theta_min         5.152
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      149.95(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3385
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -68.00  31.00   1.00    1.00    --  -43.06  38.00 120.00   99
  2  ω   -115.00 -28.00   1.00    1.00    --  -43.06 -57.00 -30.00   87
  3  ω    -58.00  -6.00   1.00    1.00    --  -43.06 125.00-180.00   52
  4  ω     29.00  96.00   1.00    1.00    --   43.06-125.00-120.00   67
  5  ω     35.00 105.00   1.00    1.00    --  104.94 -95.00  60.00   70
  6  ω     23.00 105.00   1.00    1.00    --  104.94 -95.00 -30.00   82
  7  ω    113.00 177.00   1.00    1.00    --  104.94  77.00 120.00   64
  8  ω     78.00 136.00   1.00    1.00    --  104.94  30.00  60.00   58
  9  ω     88.00 114.00   1.00    1.00    --  104.94 -30.00  60.00   26
 10  ω     42.00 110.00   1.00    1.00    --  104.94-125.00-120.00   68
 11  ω     44.00  77.00   1.00    1.00    --  104.94 -30.00  60.00   33
 12  ω     63.00 135.00   1.00    1.00    --  104.94 -66.00  40.00   72
 13  ω    102.00 165.00   1.00    1.00    --  104.94 125.00  30.00   63
 14  ω    121.00 172.00   1.00    1.00    --  104.94  30.00   0.00   51
 15  ω     83.00 108.00   1.00    1.00    --  104.94-104.00-107.18   25
 16  ω     86.00 161.00   1.00    1.00    --  104.94  45.00  90.00   75
 17  ω     26.00  62.00   1.00    1.00    --  104.94-104.00-107.18   36
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0212287000
_diffrn_orient_matrix_UB_12      0.0663548000
_diffrn_orient_matrix_UB_13      -0.2813539000
_diffrn_orient_matrix_UB_21      0.0650017000
_diffrn_orient_matrix_UB_22      -0.0863854000
_diffrn_orient_matrix_UB_23      -0.1402292000
_diffrn_orient_matrix_UB_31      -0.0581069000
_diffrn_orient_matrix_UB_32      -0.1207561000
_diffrn_orient_matrix_UB_33      -0.0543410000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                763
_reflns_number_total             821
_reflns_odcompleteness_completeness 99.89
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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       'CrysAlisPro 1.171.40.82a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.82a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.82a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.360
_refine_diff_density_min         -0.385
_refine_diff_density_rms         0.060
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.110
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     72
_refine_ls_number_reflns         821
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0383
_refine_ls_R_factor_gt           0.0357
_refine_ls_restrained_S_all      1.110
_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+0.5166P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0947
_refine_ls_wR_factor_ref         0.0982
_refine_special_details          ?
_olex2_refinement_description    
;
1. Others
 Fixed Sof: H00B(0.5) H004(0.5)
2.a Free rotating group:
 O003(H00A,H00B)
2.b Ternary CH refined with riding coordinates:
 C006(H006), C007(H007), C008(H008), C009(H009)
2.c Idealised tetrahedral OH refined as rotating group:
 O004(H004), O005(H005)
;
_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
F001 F 0.53658(7) 0.250000 0.5477(3) 0.0196(3) Uani 1 2 d S T P . .
F002 F 0.68111(5) 0.39686(10) 0.53621(19) 0.0217(3) Uani 1 1 d . . . . .
O003 O 0.63056(9) 0.750000 0.2282(3) 0.0212(4) Uani 1 2 d GS T P . .
H00A H 0.662691 0.750122 0.096142 0.032 Uiso 1 2 d G U P . .
H00B H 0.595863 0.813795 0.217562 0.032 Uiso 0.5 1 d G U P . .
O004 O 0.79287(8) 0.250000 0.2296(3) 0.0224(4) Uani 1 2 d S T P . .
H004 H 0.820170 0.231340 0.095137 0.034 Uiso 0.5 1 calc R U P . .
O005 O 0.54756(6) 0.50340(11) 0.2743(3) 0.0250(3) Uani 1 1 d . . . . .
H005 H 0.573801 0.574217 0.245296 0.038 Uiso 1 1 calc R U . . .
C006 C 0.54474(11) 0.250000 0.2582(4) 0.0139(4) Uani 1 2 d S T P . .
H006 H 0.492707 0.249999 0.174770 0.017 Uiso 1 2 calc R U P . .
C007 C 0.58692(8) 0.38326(14) 0.1690(3) 0.0146(3) Uani 1 1 d . . . . .
H007 H 0.584025 0.387986 -0.033414 0.018 Uiso 1 1 calc R U . . .
C008 C 0.67319(8) 0.38390(15) 0.2478(3) 0.0155(4) Uani 1 1 d . . . . .
H008 H 0.698291 0.465168 0.159364 0.019 Uiso 1 1 calc R U . . .
C009 C 0.71309(11) 0.250000 0.1490(4) 0.0156(4) Uani 1 2 d S T P . .
H009 H 0.711434 0.250001 -0.053855 0.019 Uiso 1 2 calc R U P . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F001 C006 1.405(2) . ?
F002 C008 1.4052(17) . ?
O003 H00A 0.8431 . ?
O003 H00B 0.85(4) 7_575 ?
O003 H00B 0.8500 . ?
O004 H004 0.82(2) 7_565 ?
O004 H004 0.8200 . ?
O004 C009 1.424(2) . ?
O005 H005 0.8200 . ?
O005 C007 1.4176(17) . ?
C006 H006 0.9800 . ?
C006 C007 1.5175(17) . ?
C006 C007 1.5176(17) 7_565 ?
C007 H007 0.9800 . ?
C007 C008 1.5293(18) . ?
C008 H008 0.9800 . ?
C008 C009 1.5182(17) . ?
C009 H009 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
H00A O003 H00B 114.3 . . ?
H00A O003 H00B 114.5 . 7_575 ?
H00B O003 H00B 90.6 . 7_575 ?
H004 O004 H004 24.9 . 7_565 ?
C009 O004 H004 109.5 . . ?
C009 O004 H004 109.5(6) . 7_565 ?
C007 O005 H005 109.5 . . ?
F001 C006 H006 108.6 . . ?
F001 C006 C007 109.27(11) . . ?
F001 C006 C007 109.27(11) . 7_565 ?
C007 C006 H006 108.6 . . ?
C007 C006 H006 108.6 7_565 . ?
C007 C006 C007 112.54(16) . 7_565 ?
O005 C007 C006 109.77(12) . . ?
O005 C007 H007 107.3 . . ?
O005 C007 C008 111.68(12) . . ?
C006 C007 H007 107.3 . . ?
C006 C007 C008 113.26(12) . . ?
C008 C007 H007 107.3 . . ?
F002 C008 C007 109.91(11) . . ?
F002 C008 H008 108.7 . . ?
F002 C008 C009 109.93(13) . . ?
C007 C008 H008 108.7 . . ?
C009 C008 C007 110.83(13) . . ?
C009 C008 H008 108.7 . . ?
O004 C009 C008 110.37(11) . 7_565 ?
O004 C009 C008 110.37(11) . . ?
O004 C009 H009 107.5 . . ?
C008 C009 C008 113.28(16) . 7_565 ?
C008 C009 H009 107.5 . . ?
C008 C009 H009 107.5 7_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
F001 C006 C007 O005 -54.50(16) . . . . ?
F001 C006 C007 C008 71.08(16) . . . . ?
F002 C008 C009 O004 -56.78(17) . . . . ?
F002 C008 C009 C008 67.56(19) . . . 7_565 ?
O005 C007 C008 F002 54.66(15) . . . . ?
O005 C007 C008 C009 176.38(12) . . . . ?
C006 C007 C008 F002 -69.88(16) . . . . ?
C006 C007 C008 C009 51.84(18) . . . . ?
C007 C006 C007 O005 -176.07(10) 7_565 . . . ?
C007 C006 C007 C008 -50.5(2) 7_565 . . . ?
C007 C008 C009 O004 -178.49(12) . . . . ?
C007 C008 C009 C008 -54.2(2) . . . 7_565 ?

_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.950
_oxdiff_exptl_absorpt_empirical_full_min 0.463
####################################################################### 
# 
# 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_svh23010_auto
_database_code_depnum_ccdc_archive 'CCDC 2306069'
_audit_update_record             
;
2023-11-06 deposited with the CCDC.	2023-12-08 downloaded from the CCDC.
;
_audit_creation_date             2023-11-06
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
shyamkumar.vadakket-haridas@uni-ulm.de
_publ_section_exptl              
;
Any special experimental details
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H15 F3 O3'
_chemical_formula_sum            'C15 H15 F3 O3'
_chemical_formula_weight         300.27
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C15 H15 O3 F3'
_chemical_oxdiff_usercomment     SVH-248
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           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                   18.1588(5)
_cell_length_b                   9.2165(2)
_cell_length_c                   16.7115(5)
_cell_angle_alpha                90
_cell_angle_beta                 92.384(3)
_cell_angle_gamma                90
_cell_volume                     2794.43(13)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    6609
_cell_measurement_temperature    150.00(14)
_cell_measurement_theta_max      72.7270
_cell_measurement_theta_min      4.8540
_shelx_estimated_absorpt_T_max   0.928
_shelx_estimated_absorpt_T_min   0.626
_exptl_absorpt_coefficient_mu    1.078
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.643
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.123a (Rigaku Oxford Diffraction, 2022)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.427
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             1248
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 6 3 0.2158
0 -6 -4 0.2170
-8 0 8 0.0346
8 1 -8 0.0180
-11 0 -3 0.0396
11 0 3 0.0267
-6 0 -9 0.0415
6 0 9 0.0358
-2 3 -9 0.0942
-6 0 10 0.0299
-9 0 7 0.0230
-11 1 3 0.0478
-12 0 -1 0.0329

_exptl_crystal_recrystallization_method ?
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.07
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
0.4761 5.7067 3.1951 0.1029 -0.0328 0.9942
0.2546 -5.5789 -3.9079 -0.1877 0.0627 -0.9802
-7.7701 -0.0246 8.4494 0.9397 -0.3311 0.0856
7.9258 0.5763 -8.2599 -0.9430 0.3326 0.0092
-11.1883 0.2434 -2.9647 0.0786 -0.9880 -0.1331
11.1557 0.1156 3.0781 -0.0776 0.9781 0.1933
-5.9063 0.4604 -9.1164 -0.5996 -0.7827 -0.1670
5.8990 0.2545 9.1469 0.5836 0.7610 0.2834
-2.0089 2.6301 -9.4787 -0.8033 -0.5545 0.2173
-5.6328 0.2254 9.7281 0.9765 -0.1278 0.1733
-9.4037 0.2371 6.8846 0.8504 -0.5199 0.0803
-11.2648 1.0205 3.0444 0.5636 -0.8184 0.1119
-11.7150 0.2600 -0.6896 0.2844 -0.9544 -0.0904

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0687
_diffrn_reflns_av_unetI/netI     0.0389
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            14602
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.495
_diffrn_reflns_theta_min         4.875
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(14)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3385
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -87.00  -6.00   1.00    1.00    --  -43.06 125.00 -30.00   81
  2  ω    -71.00  30.00   1.00    1.00    --  -43.06  57.00 -90.00  101
  3  ω    -68.00  31.00   1.00    1.00    --  -43.06  38.00  60.00   99
  4  ω   -115.00 -15.00   1.00    1.00    --  -43.06 -57.00 120.00  100
  5  ω     33.00 134.00   1.00    4.00    --  104.94 -61.00  90.00  101
  6  ω     29.00 138.00   1.00    4.00    --  104.94 -77.00-120.00  109
  7  ω     23.00 106.00   1.00    4.00    --  104.94 -95.00-180.00   83
  8  ω     23.00 106.00   1.00    4.00    --  104.94 -95.00 -30.00   83
  9  ω    103.00 178.00   1.00    4.00    --  104.94  77.00-150.00   75
 10  ω     23.00 106.00   1.00    4.00    --  104.94 -95.00   0.00   83
 11  ω    103.00 178.00   1.00    4.00    --  104.94  77.00 -60.00   75
 12  ω     29.00 133.00   1.00    4.00    --  104.94 -30.00 150.00  104
 13  ω     32.00 131.00   1.00    4.00    --  104.94 -45.00 -30.00   99
 14  ω     23.00 106.00   1.00    4.00    --  104.94 -95.00  90.00   83
 15  ω     17.00 178.00   1.00    4.00    --  104.94   0.00-150.00  161
 16  ω   -115.00 -15.00   1.00    1.00    --  -43.06 -57.00  30.00  100
 17  ω   -115.00 -15.00   1.00    1.00    --  -43.06 -57.00-150.00  100
 18  ω   -115.00 -15.00   1.00    1.00    --  -43.06 -57.00 -60.00  100
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0297900000
_diffrn_orient_matrix_UB_12      -0.0263691000
_diffrn_orient_matrix_UB_13      0.0837443000
_diffrn_orient_matrix_UB_21      0.0788295000
_diffrn_orient_matrix_UB_22      -0.0309141000
_diffrn_orient_matrix_UB_23      0.0332186000
_diffrn_orient_matrix_UB_31      0.0101447000
_diffrn_orient_matrix_UB_32      0.1622000000
_diffrn_orient_matrix_UB_33      0.0199329000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2277
_reflns_number_total             2780
_reflns_odcompleteness_completeness 99.96
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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       'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.3 (Bourhis et al., 2015)'
_refine_diff_density_max         0.515
_refine_diff_density_min         -0.285
_refine_diff_density_rms         0.071
_refine_ls_extinction_coef       0.00013(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.318
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         2780
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0677
_refine_ls_R_factor_gt           0.0556
_refine_ls_restrained_S_all      1.318
_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)+19.7736P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1737
_refine_ls_wR_factor_ref         0.1785
_refine_special_details          ?
_olex2_refinement_description    
;
1.a Ternary CH refined with riding coordinates:
 C007(H007), C008(H008), C009(H009), C00A(H00A), C00B(H00B), C00C(H00C)
1.b Secondary CH2 refined with riding coordinates:
 C00D(H00D,H00E), C00F(H00F,H00G), C00I(H00H,H00I)
1.c :
 C10(H10), C11(H11), C12(H12)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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
F001 F 0.71877(12) 0.8645(2) 0.08647(13) 0.0266(5) Uani 1 1 d . . . . .
F002 F 0.82491(12) 0.8934(2) 0.20549(13) 0.0262(5) Uani 1 1 d . . . . .
F003 F 0.66973(12) 0.9101(2) 0.23838(13) 0.0262(5) Uani 1 1 d . . . . .
O004 O 0.76866(15) 0.8071(3) 0.34889(15) 0.0240(6) Uani 1 1 d . . . . .
O005 O 0.84662(15) 0.6992(3) 0.08096(15) 0.0259(6) Uani 1 1 d . . . . .
O006 O 0.58903(15) 0.7414(3) 0.13969(17) 0.0290(7) Uani 1 1 d . . . . .
C007 C 0.7548(2) 0.7221(4) 0.2785(2) 0.0210(8) Uani 1 1 d . . . . .
H007 H 0.755345 0.617532 0.294576 0.025 Uiso 1 1 calc R U . . .
C008 C 0.8142(2) 0.7444(4) 0.2177(2) 0.0220(8) Uani 1 1 d . . . . .
H008 H 0.861326 0.701117 0.239571 0.026 Uiso 1 1 calc R U . . .
C009 C 0.7930(2) 0.6708(4) 0.1387(2) 0.0216(8) Uani 1 1 d . . . . .
H009 H 0.792097 0.563680 0.148257 0.026 Uiso 1 1 calc R U . . .
C00A C 0.6594(2) 0.6873(4) 0.1663(2) 0.0230(8) Uani 1 1 d . . . . .
H00A H 0.655330 0.580235 0.174672 0.028 Uiso 1 1 calc R U . . .
C00B C 0.7177(2) 0.7153(4) 0.1054(2) 0.0225(8) Uani 1 1 d . . . . .
H00B H 0.705452 0.658333 0.055663 0.027 Uiso 1 1 calc R U . . .
C00C C 0.6773(2) 0.7590(4) 0.2467(2) 0.0227(8) Uani 1 1 d . . . . .
H00C H 0.641186 0.724175 0.286069 0.027 Uiso 1 1 calc R U . . .
C00D C 0.8230(2) 0.7421(5) 0.4023(2) 0.0274(9) Uani 1 1 d . . . . .
H00D H 0.870567 0.734270 0.375726 0.033 Uiso 1 1 calc R U . . .
H00E H 0.807144 0.643449 0.417379 0.033 Uiso 1 1 calc R U . . .
C00E C 0.8316(2) 0.8335(5) 0.4738(2) 0.0274(9) Uani 1 1 d . . . . .
C00F C 0.8835(2) 0.5722(5) 0.0533(2) 0.0317(10) Uani 1 1 d . . . . .
H00F H 0.900587 0.590102 -0.001353 0.038 Uiso 1 1 calc R U . . .
H00G H 0.848230 0.490215 0.050254 0.038 Uiso 1 1 calc R U . . .
C10 C 0.8396(2) 0.9077(5) 0.5313(2) 0.0342(10) Uani 1 1 d . . . . .
H10 H 0.845948 0.967263 0.577507 0.041 Uiso 1 1 calc R U . . .
C00H C 0.9467(3) 0.5326(5) 0.1062(3) 0.0353(10) Uani 1 1 d . . . . .
C00I C 0.5496(2) 0.6551(5) 0.0814(3) 0.0360(10) Uani 1 1 d . . . . .
H00H H 0.582469 0.631430 0.037429 0.043 Uiso 1 1 calc R U . . .
H00I H 0.507509 0.711713 0.058383 0.043 Uiso 1 1 calc R U . . .
C00J C 0.5219(2) 0.5193(6) 0.1159(3) 0.0404(11) Uani 1 1 d . . . . .
C11 C 0.9986(3) 0.5029(6) 0.1474(3) 0.0503(14) Uani 1 1 d . . . . .
H11 H 1.040466 0.478826 0.180718 0.060 Uiso 1 1 calc R U . . .
C12 C 0.4984(3) 0.4106(6) 0.1410(3) 0.0519(14) Uani 1 1 d . . . . .
H12 H 0.479311 0.322588 0.161256 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
F001 C00B 1.411(4) . ?
F002 C008 1.403(4) . ?
F003 C00C 1.405(4) . ?
O004 C007 1.427(4) . ?
O004 C00D 1.434(4) . ?
O005 C009 1.423(4) . ?
O005 C00F 1.435(5) . ?
O006 C00A 1.425(4) . ?
O006 C00I 1.427(5) . ?
C007 H007 1.0000 . ?
C007 C008 1.526(5) . ?
C007 C00C 1.522(5) . ?
C008 H008 1.0000 . ?
C008 C009 1.520(5) . ?
C009 H009 1.0000 . ?
C009 C00B 1.511(5) . ?
C00A H00A 1.0000 . ?
C00A C00B 1.521(5) . ?
C00A C00C 1.521(5) . ?
C00B H00B 1.0000 . ?
C00C H00C 1.0000 . ?
C00D H00D 0.9900 . ?
C00D H00E 0.9900 . ?
C00D C00E 1.465(5) . ?
C00E C10 1.184(6) . ?
C00F H00F 0.9900 . ?
C00F H00G 0.9900 . ?
C00F C00H 1.466(6) . ?
C10 H10 0.9500 . ?
C00H C11 1.176(7) . ?
C00I H00H 0.9900 . ?
C00I H00I 0.9900 . ?
C00I C00J 1.475(7) . ?
C00J C12 1.174(7) . ?
C11 H11 0.9500 . ?
C12 H12 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
C007 O004 C00D 112.1(3) . . ?
C009 O005 C00F 114.2(3) . . ?
C00A O006 C00I 115.8(3) . . ?
O004 C007 H007 108.0 . . ?
O004 C007 C008 111.7(3) . . ?
O004 C007 C00C 107.1(3) . . ?
C008 C007 H007 108.0 . . ?
C00C C007 H007 108.0 . . ?
C00C C007 C008 114.0(3) . . ?
F002 C008 C007 109.6(3) . . ?
F002 C008 H008 108.7 . . ?
F002 C008 C009 110.0(3) . . ?
C007 C008 H008 108.7 . . ?
C009 C008 C007 111.0(3) . . ?
C009 C008 H008 108.7 . . ?
O005 C009 C008 110.6(3) . . ?
O005 C009 H009 107.9 . . ?
O005 C009 C00B 109.5(3) . . ?
C008 C009 H009 107.9 . . ?
C00B C009 C008 113.0(3) . . ?
C00B C009 H009 107.9 . . ?
O006 C00A H00A 108.6 . . ?
O006 C00A C00B 111.9(3) . . ?
O006 C00A C00C 106.2(3) . . ?
C00B C00A H00A 108.6 . . ?
C00B C00A C00C 112.9(3) . . ?
C00C C00A H00A 108.6 . . ?
F001 C00B C009 109.0(3) . . ?
F001 C00B C00A 109.4(3) . . ?
F001 C00B H00B 109.3 . . ?
C009 C00B C00A 110.6(3) . . ?
C009 C00B H00B 109.3 . . ?
C00A C00B H00B 109.3 . . ?
F003 C00C C007 109.9(3) . . ?
F003 C00C C00A 109.0(3) . . ?
F003 C00C H00C 108.7 . . ?
C007 C00C H00C 108.7 . . ?
C00A C00C C007 111.8(3) . . ?
C00A C00C H00C 108.7 . . ?
O004 C00D H00D 110.0 . . ?
O004 C00D H00E 110.0 . . ?
O004 C00D C00E 108.4(3) . . ?
H00D C00D H00E 108.4 . . ?
C00E C00D H00D 110.0 . . ?
C00E C00D H00E 110.0 . . ?
C10 C00E C00D 179.1(5) . . ?
O005 C00F H00F 109.2 . . ?
O005 C00F H00G 109.2 . . ?
O005 C00F C00H 111.9(3) . . ?
H00F C00F H00G 107.9 . . ?
C00H C00F H00F 109.2 . . ?
C00H C00F H00G 109.2 . . ?
C00E C10 H10 180.0 . . ?
C11 C00H C00F 178.3(6) . . ?
O006 C00I H00H 109.2 . . ?
O006 C00I H00I 109.2 . . ?
O006 C00I C00J 112.1(4) . . ?
H00H C00I H00I 107.9 . . ?
C00J C00I H00H 109.2 . . ?
C00J C00I H00I 109.2 . . ?
C12 C00J C00I 177.7(5) . . ?
C00H C11 H11 180.0 . . ?
C00J C12 H12 180.0 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
F002 C008 C009 O005 55.2(4) . . . . ?
F002 C008 C009 C00B -68.0(4) . . . . ?
O004 C007 C008 F002 -50.0(4) . . . . ?
O004 C007 C008 C009 -171.7(3) . . . . ?
O004 C007 C00C F003 52.3(4) . . . . ?
O004 C007 C00C C00A 173.6(3) . . . . ?
O005 C009 C00B F001 -59.2(4) . . . . ?
O005 C009 C00B C00A -179.5(3) . . . . ?
O006 C00A C00B F001 54.1(4) . . . . ?
O006 C00A C00B C009 174.2(3) . . . . ?
O006 C00A C00C F003 -52.6(4) . . . . ?
O006 C00A C00C C007 -174.4(3) . . . . ?
C007 O004 C00D C00E -177.9(3) . . . . ?
C007 C008 C009 O005 176.6(3) . . . . ?
C007 C008 C009 C00B 53.4(4) . . . . ?
C008 C007 C00C F003 -71.7(4) . . . . ?
C008 C007 C00C C00A 49.6(4) . . . . ?
C008 C009 C00B F001 64.6(4) . . . . ?
C008 C009 C00B C00A -55.7(4) . . . . ?
C009 O005 C00F C00H -85.5(4) . . . . ?
C00A O006 C00I C00J 71.4(5) . . . . ?
C00B C00A C00C F003 70.3(4) . . . . ?
C00B C00A C00C C007 -51.5(4) . . . . ?
C00C C007 C008 F002 71.4(4) . . . . ?
C00C C007 C008 C009 -50.2(4) . . . . ?
C00C C00A C00B F001 -65.6(4) . . . . ?
C00C C00A C00B C009 54.5(4) . . . . ?
C00D O004 C007 C008 -79.6(4) . . . . ?
C00D O004 C007 C00C 155.0(3) . . . . ?
C00F O005 C009 C008 117.6(3) . . . . ?
C00F O005 C009 C00B -117.2(3) . . . . ?
C00I O006 C00A C00B 77.5(4) . . . . ?
C00I O006 C00A C00C -158.9(3) . . . . ?


_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.235
_oxdiff_exptl_absorpt_empirical_full_min 0.450
####################################################################### 
# 
# 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_svh22076
_database_code_depnum_ccdc_archive 'CCDC 2306058'
_audit_update_record             
;
2023-11-06 deposited with the CCDC.	2023-12-08 downloaded from the CCDC.
;
_audit_creation_date             2023-11-06
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
shyamkumar.vadakket-haridas@uni-ulm.de
_publ_section_exptl              
;
Any special experimental details
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C10 H15 F3 O4'
_chemical_formula_sum            'C10 H15 F3 O4'
_chemical_formula_weight         256.22
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C10 H15 F3 O4'
_chemical_oxdiff_usercomment     SVH-223
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   6.47780(10)
_cell_length_b                   8.90490(10)
_cell_length_c                   19.2107(2)
_cell_angle_alpha                90
_cell_angle_beta                 98.9640(10)
_cell_angle_gamma                90
_cell_volume                     1094.62(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    10831
_cell_measurement_temperature    150.00(14)
_cell_measurement_theta_max      72.8400
_cell_measurement_theta_min      4.6340
_shelx_estimated_absorpt_T_max   0.847
_shelx_estimated_absorpt_T_min   0.633
_exptl_absorpt_coefficient_mu    1.322
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.497
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.123a (Rigaku Oxford Diffraction, 2022)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.555
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             536
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 0 12 0.0543
0 0 -12 0.0723
4 -3 -6 0.1899
4 -3 0 0.1937
-4 0 3 0.1838
4 1 -3 0.1794
0 -6 4 0.1048
-3 4 -1 0.1437
3 4 -4 0.1581
0 4 9 0.0669
-4 0 -4 0.1555
3 2 8 0.1268
0 -4 -9 0.0852
0 4 -9 0.0837
1 -4 8 0.1218
-3 3 -1 0.1512
0 6 0 0.0836
2 5 -1 0.1340
0 -6 0 0.0990
3 4 4 0.1197

_exptl_crystal_preparation       'Solvent layering/Methanol/n-hexane'
_exptl_crystal_recrystallization_method 'Solvent layering/Methanol/n-hexane'
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.13
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-0.1177 -0.0899 12.3610 -0.9935 -0.0798 -0.0813
0.2016 0.0289 -12.3918 0.9951 0.0798 0.0588
3.5363 -2.5102 -5.6062 0.4134 0.0301 -0.9100
3.6573 -2.6839 0.3594 -0.0680 -0.0088 -0.9976
-4.1982 -0.1181 2.6263 -0.1928 0.4713 0.8606
4.1375 0.8787 -3.0912 0.2367 -0.5764 -0.7821
-0.1571 -5.5156 3.7334 -0.3451 0.8262 -0.4452
-2.7105 4.2692 -1.1706 0.1420 -0.3332 0.9321
3.1454 3.6023 -4.2854 0.3599 -0.8687 -0.3404
-0.0819 4.1433 8.6234 -0.6581 -0.6967 0.2854
-3.6585 0.4538 -4.3032 0.3663 0.3829 0.8481
2.5109 1.9759 7.7789 -0.6202 -0.6531 -0.4346
-0.3182 -3.9517 -8.7944 0.6753 0.7144 -0.1835
0.0249 4.1317 -8.6223 0.7271 -0.5581 0.3999
0.7048 -4.2760 7.6972 -0.6573 0.5053 -0.5591
-3.3893 3.2061 -0.9694 0.1201 -0.0960 0.9881
-0.0302 5.7799 -0.2526 0.0685 -0.8753 0.4786
2.4243 4.7209 -0.6396 0.0795 -0.9889 -0.1255
-0.2348 -5.7719 0.2991 -0.0710 0.9038 -0.4221
2.7303 3.5997 4.1259 -0.3141 -0.8939 -0.3198

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0550
_diffrn_reflns_av_unetI/netI     0.0222
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            15359
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.001
_diffrn_reflns_theta_min         4.661
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(14)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3385
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -84.00  37.00   1.00    1.00    --  -43.06  19.00   0.00  121
  2  ω   -117.00 -19.00   1.00    1.00    --  -43.06 -38.00-180.00   98
  3  ω     27.00  99.00   1.00    1.00    --   43.06-125.00 150.00   72
  4  ω     27.00  99.00   1.00    1.00    --   43.06-125.00 120.00   72
  5  ω     27.00  99.00   1.00    1.00    --   43.06-125.00  30.00   72
  6  ω     32.00 131.00   1.00    1.00    --  104.94 -45.00 -90.00   99
  7  ω     33.00 134.00   1.00    1.00    --  104.94 -61.00 150.00  101
  8  ω     23.00 106.00   1.00    1.00    --  104.94 -95.00  90.00   83
  9  ω     23.00 106.00   1.00    1.00    --  104.94 -95.00 150.00   83
 10  ω    103.00 178.00   1.00    1.00    --  104.94  77.00-120.00   75
 11  ω    103.00 178.00   1.00    1.00    --  104.94  77.00-150.00   75
 12  ω     29.00 133.00   1.00    1.00    --  104.94 -30.00-120.00  104
 13  ω     32.00 112.00   1.00    1.00    --  104.94-125.00 -90.00   80
 14  ω     23.00 106.00   1.00    1.00    --  104.94 -95.00  30.00   83
 15  ω     23.00 158.00   1.00    1.00    --  104.94 -15.00  60.00  135
 16  ω     23.00 106.00   1.00    1.00    --  104.94 -95.00 -60.00   83
 17  ω   -115.00 -15.00   1.00    1.00    --  -43.06 -57.00  60.00  100
 18  ω   -115.00 -15.00   1.00    1.00    --  -43.06 -57.00   0.00  100
 19  ω   -115.00 -15.00   1.00    1.00    --  -43.06 -57.00 -60.00  100
 20  ω   -115.00 -15.00   1.00    1.00    --  -43.06 -57.00-120.00  100
 21  ω   -115.00 -15.00   1.00    1.00    --  -43.06 -57.00 120.00  100
 22  ω     76.00 177.00   1.00    1.00    --  104.94  61.00-150.00  101
 23  ω     52.00 178.00   1.00    1.00    --  104.94  15.00 150.00  126
 24  ω     76.00 165.00   1.00    1.00    --  104.94  61.00  30.00   89
 25  ω     76.00 177.00   1.00    1.00    --  104.94  61.00 -30.00  101
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0045832000
_diffrn_orient_matrix_UB_12      0.0083150000
_diffrn_orient_matrix_UB_13      -0.0803560000
_diffrn_orient_matrix_UB_21      -0.1133920000
_diffrn_orient_matrix_UB_22      -0.1524151000
_diffrn_orient_matrix_UB_23      -0.0086415000
_diffrn_orient_matrix_UB_31      -0.2122964000
_diffrn_orient_matrix_UB_32      0.0813510000
_diffrn_orient_matrix_UB_33      -0.0080095000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2059
_reflns_number_total             2170
_reflns_odcompleteness_completeness 99.86
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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       'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.344
_refine_diff_density_min         -0.216
_refine_diff_density_rms         0.048
_refine_ls_extinction_coef       0.0082(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     158
_refine_ls_number_reflns         2170
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0339
_refine_ls_R_factor_gt           0.0324
_refine_ls_restrained_S_all      1.050
_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)+(0.0481P)²+0.3943P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0883
_refine_ls_wR_factor_ref         0.0897
_refine_special_details          ?
_olex2_refinement_description    
;
1.a Ternary CH refined with riding coordinates:
 C008(H008), C009(H009), C00B(H00B), C00C(H00C), C00D(H00D), C00E(H00E)
1.b Secondary CH2 refined with riding coordinates:
 C00F(H00A,H00F), C00G(H00G,H00H)
1.c Idealised Me refined as rotating group:
 C00H(H00I,H00J,H00K)
1.d Idealised tetrahedral OH refined as rotating group:
 O8(H8), O005(H005)
;
_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
F001 F 0.33955(11) 0.21824(8) 0.75734(4) 0.0230(2) Uani 1 1 d . . . . .
F002 F 0.10272(11) 0.09815(7) 0.63555(4) 0.0236(2) Uani 1 1 d . . . . .
F003 F 0.50587(11) 0.22179(8) 0.63094(4) 0.0247(2) Uani 1 1 d . . . . .
O8 O -0.09206(12) 0.24697(9) 0.73471(4) 0.0198(2) Uani 1 1 d . . . . .
H8 H -0.205755 0.292175 0.734963 0.030 Uiso 1 1 calc R U . . .
O005 O 0.59246(13) 0.45294(9) 0.72570(5) 0.0221(2) Uani 1 1 d . . . . .
H005 H 0.604075 0.537796 0.745016 0.033 Uiso 1 1 calc R U . . .
O006 O 0.18642(14) 0.24387(9) 0.51633(4) 0.0213(2) Uani 1 1 d . . . . .
O007 O 0.22460(15) 0.46037(10) 0.45924(5) 0.0274(2) Uani 1 1 d . . . . .
C008 C 0.38634(18) 0.43546(13) 0.68844(6) 0.0175(3) Uani 1 1 d . . . . .
H008 H 0.327077 0.538023 0.677589 0.021 Uiso 1 1 calc R U . . .
C009 C 0.24714(18) 0.35528(12) 0.73341(6) 0.0178(3) Uani 1 1 d . . . . .
H009 H 0.233143 0.419542 0.775112 0.021 Uiso 1 1 calc R U . . .
C00A C 0.21242(18) 0.32494(14) 0.45868(6) 0.0205(3) Uani 1 1 d . . . . .
C00B C 0.17818(18) 0.32841(13) 0.57984(6) 0.0178(3) Uani 1 1 d . . . . .
H00B H 0.113008 0.427934 0.565920 0.021 Uiso 1 1 calc R U . . .
C00C C 0.03093(17) 0.32715(12) 0.69202(6) 0.0171(3) Uani 1 1 d . . . . .
H00C H -0.036811 0.427033 0.680930 0.021 Uiso 1 1 calc R U . . .
C00D C 0.39717(18) 0.35700(13) 0.61878(6) 0.0186(3) Uani 1 1 d . . . . .
H00D H 0.473148 0.423204 0.589196 0.022 Uiso 1 1 calc R U . . .
C00E C 0.03543(18) 0.24590(13) 0.62243(6) 0.0181(3) Uani 1 1 d . . . . .
H00E H -0.109142 0.244420 0.595075 0.022 Uiso 1 1 calc R U . . .
C00F C 0.2240(2) 0.22591(16) 0.39640(6) 0.0282(3) Uani 1 1 d . . . . .
H00A H 0.245680 0.289148 0.355777 0.034 Uiso 1 1 calc R U . . .
H00F H 0.089116 0.172820 0.383711 0.034 Uiso 1 1 calc R U . . .
C00G C 0.3996(2) 0.11034(15) 0.41007(7) 0.0314(3) Uani 1 1 d . . . . .
H00G H 0.371436 0.041834 0.448081 0.038 Uiso 1 1 calc R U . . .
H00H H 0.400073 0.049522 0.366957 0.038 Uiso 1 1 calc R U . . .
C00H C 0.6133(2) 0.18046(19) 0.43092(8) 0.0393(4) Uani 1 1 d . . . . .
H00I H 0.646275 0.243309 0.392240 0.059 Uiso 1 1 calc R U . . .
H00J H 0.718466 0.101060 0.440906 0.059 Uiso 1 1 calc R U . . .
H00K H 0.613353 0.242396 0.473088 0.059 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F001 C009 1.4047(13) . ?
F002 C00E 1.3966(13) . ?
F003 C00D 1.3960(13) . ?
O8 H8 0.8400 . ?
O8 C00C 1.4215(13) . ?
O005 H005 0.8400 . ?
O005 C008 1.4217(14) . ?
O006 C00A 1.3544(14) . ?
O006 C00B 1.4417(13) . ?
O007 C00A 1.2086(16) . ?
C008 H008 1.0000 . ?
C008 C009 1.5205(15) . ?
C008 C00D 1.5209(15) . ?
C009 H009 1.0000 . ?
C009 C00C 1.5197(15) . ?
C00A C00F 1.4975(17) . ?
C00B H00B 1.0000 . ?
C00B C00D 1.5186(16) . ?
C00B C00E 1.5165(16) . ?
C00C H00C 1.0000 . ?
C00C C00E 1.5245(16) . ?
C00D H00D 1.0000 . ?
C00E H00E 1.0000 . ?
C00F H00A 0.9900 . ?
C00F H00F 0.9900 . ?
C00F C00G 1.5258(19) . ?
C00G H00G 0.9900 . ?
C00G H00H 0.9900 . ?
C00G C00H 1.515(2) . ?
C00H H00I 0.9800 . ?
C00H H00J 0.9800 . ?
C00H H00K 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
C00C O8 H8 109.5 . . ?
C008 O005 H005 109.5 . . ?
C00A O006 C00B 116.07(9) . . ?
O005 C008 H008 107.8 . . ?
O005 C008 C009 111.03(9) . . ?
O005 C008 C00D 108.95(9) . . ?
C009 C008 H008 107.8 . . ?
C009 C008 C00D 113.39(9) . . ?
C00D C008 H008 107.8 . . ?
F001 C009 C008 109.49(9) . . ?
F001 C009 H009 108.8 . . ?
F001 C009 C00C 109.81(9) . . ?
C008 C009 H009 108.8 . . ?
C00C C009 C008 111.10(9) . . ?
C00C C009 H009 108.8 . . ?
O006 C00A C00F 111.57(11) . . ?
O007 C00A O006 122.74(11) . . ?
O007 C00A C00F 125.69(11) . . ?
O006 C00B H00B 107.8 . . ?
O006 C00B C00D 110.46(9) . . ?
O006 C00B C00E 108.04(9) . . ?
C00D C00B H00B 107.8 . . ?
C00E C00B H00B 107.8 . . ?
C00E C00B C00D 114.63(9) . . ?
O8 C00C C009 109.55(9) . . ?
O8 C00C H00C 107.6 . . ?
O8 C00C C00E 110.89(9) . . ?
C009 C00C H00C 107.6 . . ?
C009 C00C C00E 113.27(9) . . ?
C00E C00C H00C 107.6 . . ?
F003 C00D C008 109.89(9) . . ?
F003 C00D C00B 110.24(9) . . ?
F003 C00D H00D 108.9 . . ?
C008 C00D H00D 108.9 . . ?
C00B C00D C008 110.05(9) . . ?
C00B C00D H00D 108.9 . . ?
F002 C00E C00B 110.76(9) . . ?
F002 C00E C00C 109.68(9) . . ?
F002 C00E H00E 108.8 . . ?
C00B C00E C00C 109.86(9) . . ?
C00B C00E H00E 108.8 . . ?
C00C C00E H00E 108.8 . . ?
C00A C00F H00A 109.0 . . ?
C00A C00F H00F 109.0 . . ?
C00A C00F C00G 112.86(10) . . ?
H00A C00F H00F 107.8 . . ?
C00G C00F H00A 109.0 . . ?
C00G C00F H00F 109.0 . . ?
C00F C00G H00G 108.9 . . ?
C00F C00G H00H 108.9 . . ?
H00G C00G H00H 107.8 . . ?
C00H C00G C00F 113.17(11) . . ?
C00H C00G H00G 108.9 . . ?
C00H C00G H00H 108.9 . . ?
C00G C00H H00I 109.5 . . ?
C00G C00H H00J 109.5 . . ?
C00G C00H H00K 109.5 . . ?
H00I C00H H00J 109.5 . . ?
H00I C00H H00K 109.5 . . ?
H00J C00H H00K 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
F001 C009 C00C O8 56.45(11) . . . . ?
F001 C009 C00C C00E -67.93(11) . . . . ?
O8 C00C C00E F002 -54.54(12) . . . . ?
O8 C00C C00E C00B -176.52(8) . . . . ?
O005 C008 C009 F001 -54.72(11) . . . . ?
O005 C008 C009 C00C -176.18(9) . . . . ?
O005 C008 C00D F003 55.02(12) . . . . ?
O005 C008 C00D C00B 176.59(9) . . . . ?
O006 C00A C00F C00G -57.64(14) . . . . ?
O006 C00B C00D F003 -54.23(12) . . . . ?
O006 C00B C00D C008 -175.60(9) . . . . ?
O006 C00B C00E F002 55.74(11) . . . . ?
O006 C00B C00E C00C 177.07(8) . . . . ?
O007 C00A C00F C00G 122.22(14) . . . . ?
C008 C009 C00C O8 177.72(9) . . . . ?
C008 C009 C00C C00E 53.34(12) . . . . ?
C009 C008 C00D F003 -69.18(12) . . . . ?
C009 C008 C00D C00B 52.40(13) . . . . ?
C009 C00C C00E F002 69.11(12) . . . . ?
C009 C00C C00E C00B -52.87(12) . . . . ?
C00A O006 C00B C00D -85.52(11) . . . . ?
C00A O006 C00B C00E 148.37(9) . . . . ?
C00A C00F C00G C00H -57.97(15) . . . . ?
C00B O006 C00A O007 -1.25(16) . . . . ?
C00B O006 C00A C00F 178.61(10) . . . . ?
C00D C008 C009 F001 68.34(12) . . . . ?
C00D C008 C009 C00C -53.12(13) . . . . ?
C00D C00B C00E F002 -67.88(12) . . . . ?
C00D C00B C00E C00C 53.45(13) . . . . ?
C00E C00B C00D F003 68.09(12) . . . . ?
C00E C00B C00D C008 -53.28(13) . . . . ?


_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.696
_oxdiff_exptl_absorpt_empirical_full_min 0.679
