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

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

data_mo_JMV0801_0m
_database_code_depnum_ccdc_archive 'CCDC 2128831'
loop_
_audit_author_name
_audit_author_address
'Jordi Mestre'
;URV
Spain
;
_audit_update_record             
;
2021-12-15 deposited with the CCDC.	2023-03-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C25 H35 F3 O13'
_chemical_formula_weight         600.53

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

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

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

_cell_length_a                   12.4505(8)
_cell_length_b                   9.7494(7)
_cell_length_c                   12.7672(8)
_cell_angle_alpha                90
_cell_angle_beta                 108.262(2)
_cell_angle_gamma                90
_cell_volume                     1471.69(17)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9957
_cell_measurement_theta_min      2.68
_cell_measurement_theta_max      34.49

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.355
_exptl_crystal_F_000             632
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    0.120
_shelx_estimated_absorpt_T_min   0.976
_shelx_estimated_absorpt_T_max   0.994
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7185
_exptl_absorpt_correction_T_max  0.7469
_exptl_absorpt_process_details   SADABS-2014/4
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Microfocus source E025 IuS'
_diffrn_source_type              'Bruker APEX DUO'
_diffrn_source_power             50
_diffrn_source_current           0.6
_diffrn_source_size              '0.2 mm x 0.2 mm fine focus'
_diffrn_radiation_monochromator  'Quazar MX Multilayer Optics'
_diffrn_detector_type            '4K CCD area detector APEX II'
_diffrn_measurement_device_type  'APEX DUO Kappa 4-axis goniometer'
_diffrn_measurement_method       
;
 Fullsphere data collection, phi and omega scans
;
_diffrn_detector_area_resol_mean 512
_diffrn_reflns_number            33703
_diffrn_reflns_av_unetI/netI     0.0284
_diffrn_reflns_av_R_equivalents  0.0233
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.680
_diffrn_reflns_theta_max         35.091
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.936
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.936
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.893
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             11662
_reflns_number_gt                10601
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.822
_reflns_Friedel_fraction_max     0.846
_reflns_Friedel_fraction_full    0.988

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

_computing_data_collection       'Bruker APEX2 v2014.9-0'
_computing_cell_refinement       'Bruker APEX2 v2014.9-0'
_computing_data_reduction        'Bruker APEX2 v2014.9-0'
_computing_structure_solution    Sir2014
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    
'shelXle (Hübschle, Sheldrick and Dittirch, 2011)'
_computing_publication_material  'SHELXL-2018/3 (Sheldrick, 2018)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0535P)²+0.0677P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 4308 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.14(13)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         11662
_refine_ls_number_parameters     377
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0413
_refine_ls_R_factor_gt           0.0360
_refine_ls_wR_factor_ref         0.0917
_refine_ls_wR_factor_gt          0.0886
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_restrained_S_all      1.031
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.26294(9) 0.76753(12) 0.32589(10) 0.0355(2) Uani 1 1 d . . . . .
F2 F 0.23516(10) 0.55045(12) 0.31971(9) 0.0366(2) Uani 1 1 d . . . . .
F3 F 0.11540(7) 0.68378(12) 0.20883(9) 0.0342(2) Uani 1 1 d . . . . .
O1 O 0.46997(8) 0.59306(11) 0.14946(8) 0.01949(18) Uani 1 1 d . . . . .
O2 O 0.13112(7) 0.57257(11) 0.01811(8) 0.01892(18) Uani 1 1 d . . . . .
O3 O 0.04110(10) 0.40323(14) 0.07691(13) 0.0363(3) Uani 1 1 d . . . . .
O4 O 0.26746(8) 0.36383(10) -0.03387(9) 0.02134(19) Uani 1 1 d . . . . .
O5 O 0.19986(11) 0.47267(13) -0.19778(10) 0.0329(3) Uani 1 1 d . . . . .
O6 O 0.61559(8) 0.39083(13) 0.10610(9) 0.0247(2) Uani 1 1 d . . . . .
O7 O 0.69798(9) 0.42454(14) -0.02398(10) 0.0281(2) Uani 1 1 d . . . . .
O8 O 0.46281(8) 0.74592(11) 0.28003(8) 0.01961(18) Uani 1 1 d . . . . .
O9 O 0.57750(8) 0.57170(10) 0.47900(8) 0.01729(17) Uani 1 1 d . . . . .
O10 O 0.79554(8) 0.69434(13) 0.49061(9) 0.0264(2) Uani 1 1 d . . . . .
O11 O 0.82099(8) 0.58314(11) 0.65187(9) 0.0229(2) Uani 1 1 d . . . . .
O12 O 0.57129(8) 0.73081(11) 0.69373(8) 0.02018(18) Uani 1 1 d . . . . .
O13 O 0.45788(8) 0.56842(11) 0.58603(8) 0.02009(18) Uani 1 1 d . . . . .
C1 C 0.28930(10) 0.64709(14) 0.17335(11) 0.0167(2) Uani 1 1 d . . . . .
H1 H 0.280018 0.733939 0.129732 0.020 Uiso 1 1 calc R U . . .
C2 C 0.23816(10) 0.52897(13) 0.09322(11) 0.0164(2) Uani 1 1 d . . . . .
H2 H 0.226792 0.446960 0.135600 0.020 Uiso 1 1 calc R U . . .
C3 C 0.31091(10) 0.49020(13) 0.02173(11) 0.0167(2) Uani 1 1 d . . . . .
H3 H 0.308150 0.564215 -0.033284 0.020 Uiso 1 1 calc R U . . .
C4 C 0.43221(10) 0.46676(14) 0.09451(11) 0.0182(2) Uani 1 1 d . . . . .
H4 H 0.435136 0.392478 0.149349 0.022 Uiso 1 1 calc R U . . .
C5 C 0.41664(10) 0.62371(14) 0.23064(11) 0.0175(2) Uani 1 1 d . . . . .
H5 H 0.429392 0.548392 0.286377 0.021 Uiso 1 1 calc R U . . .
C6 C 0.22638(11) 0.66284(15) 0.25729(12) 0.0215(2) Uani 1 1 d . . . . .
C7 C 0.03815(11) 0.49806(15) 0.01584(13) 0.0218(3) Uani 1 1 d . . . . .
C8 C -0.06345(12) 0.55131(19) -0.07091(14) 0.0299(3) Uani 1 1 d . . . . .
H8A H -0.061243 0.521977 -0.143621 0.045 Uiso 1 1 calc R U . . .
H8B H -0.064056 0.651728 -0.067748 0.045 Uiso 1 1 calc R U . . .
H8C H -0.131902 0.515254 -0.058426 0.045 Uiso 1 1 calc R U . . .
C9 C 0.21415(12) 0.36895(16) -0.14444(13) 0.0233(3) Uani 1 1 d . . . . .
C10 C 0.17838(18) 0.2280(2) -0.18874(18) 0.0387(4) Uani 1 1 d . . . . .
H10A H 0.151477 0.230993 -0.269529 0.058 Uiso 1 1 calc R U . . .
H10B H 0.117358 0.195698 -0.161687 0.058 Uiso 1 1 calc R U . . .
H10C H 0.242925 0.165325 -0.163961 0.058 Uiso 1 1 calc R U . . .
C11 C 0.50993(11) 0.43333(17) 0.02819(12) 0.0230(3) Uani 1 1 d . . . . .
H11A H 0.477619 0.358732 -0.024963 0.028 Uiso 1 1 calc R U . . .
H11B H 0.521160 0.515008 -0.013258 0.028 Uiso 1 1 calc R U . . .
C12 C 0.70488(10) 0.38971(13) 0.06817(12) 0.0177(2) Uani 1 1 d . . . . .
C13 C 0.80846(11) 0.33918(16) 0.15495(13) 0.0240(3) Uani 1 1 d . . . . .
H13A H 0.797961 0.242923 0.171586 0.036 Uiso 1 1 calc R U . . .
H13B H 0.821409 0.394380 0.221925 0.036 Uiso 1 1 calc R U . . .
H13C H 0.873863 0.347150 0.128174 0.036 Uiso 1 1 calc R U . . .
C14 C 0.58043(10) 0.73835(15) 0.34406(11) 0.0193(2) Uani 1 1 d . . . . .
H14A H 0.618371 0.824910 0.335434 0.023 Uiso 1 1 calc R U . . .
H14B H 0.616591 0.662635 0.315751 0.023 Uiso 1 1 calc R U . . .
C15 C 0.59645(10) 0.71462(13) 0.46500(11) 0.0165(2) Uani 1 1 d . . . . .
H15 H 0.539873 0.770180 0.487571 0.020 Uiso 1 1 calc R U . . .
C16 C 0.71494(11) 0.75372(14) 0.53603(12) 0.0192(2) Uani 1 1 d . . . . .
H16 H 0.723489 0.855740 0.540431 0.023 Uiso 1 1 calc R U . . .
C17 C 0.87717(11) 0.62061(16) 0.57468(13) 0.0231(3) Uani 1 1 d . . . . .
C18 C 0.74449(11) 0.69116(14) 0.65274(12) 0.0197(2) Uani 1 1 d . . . . .
H18 H 0.781737 0.761015 0.709945 0.024 Uiso 1 1 calc R U . . .
C19 C 0.64501(11) 0.62542(14) 0.67860(11) 0.0193(2) Uani 1 1 d . . . . .
H19 H 0.672570 0.568057 0.746732 0.023 Uiso 1 1 calc R U . . .
C20 C 0.46271(11) 0.66711(14) 0.67096(11) 0.0195(2) Uani 1 1 d . . . . .
C21 C 0.56837(10) 0.53978(13) 0.58322(11) 0.0173(2) Uani 1 1 d . . . . .
H21 H 0.585139 0.440194 0.598859 0.021 Uiso 1 1 calc R U . . .
C22 C 0.90781(15) 0.4905(2) 0.52591(19) 0.0381(4) Uani 1 1 d . . . . .
H22A H 0.839142 0.436991 0.491525 0.057 Uiso 1 1 calc R U . . .
H22B H 0.960286 0.436116 0.584448 0.057 Uiso 1 1 calc R U . . .
H22C H 0.943832 0.514106 0.470181 0.057 Uiso 1 1 calc R U . . .
C23 C 0.97900(12) 0.70991(19) 0.62896(16) 0.0323(3) Uani 1 1 d . . . . .
H23A H 1.014357 0.738266 0.573803 0.049 Uiso 1 1 calc R U . . .
H23B H 1.033667 0.657910 0.687531 0.049 Uiso 1 1 calc R U . . .
H23C H 0.954863 0.791318 0.660671 0.049 Uiso 1 1 calc R U . . .
C24 C 0.45344(14) 0.59394(16) 0.77279(12) 0.0254(3) Uani 1 1 d . . . . .
H24A H 0.379094 0.550095 0.755628 0.038 Uiso 1 1 calc R U . . .
H24B H 0.462514 0.660496 0.832468 0.038 Uiso 1 1 calc R U . . .
H24C H 0.512726 0.524005 0.795983 0.038 Uiso 1 1 calc R U . . .
C25 C 0.37170(13) 0.77348(16) 0.62701(13) 0.0238(3) Uani 1 1 d . . . . .
H25A H 0.382278 0.817786 0.562040 0.036 Uiso 1 1 calc R U . . .
H25B H 0.376364 0.842560 0.684022 0.036 Uiso 1 1 calc R U . . .
H25C H 0.297329 0.729182 0.606401 0.036 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 1.3290(18) . ?
F2 C6 1.3391(18) . ?
F3 C6 1.3408(16) . ?
O1 C4 1.4223(17) . ?
O1 C5 1.4268(15) . ?
O2 C7 1.3592(15) . ?
O2 C2 1.4407(15) . ?
O3 C7 1.203(2) . ?
O4 C9 1.3596(19) . ?
O4 C3 1.4401(17) . ?
O5 C9 1.201(2) . ?
O6 C12 1.3445(15) . ?
O6 C11 1.4394(16) . ?
O7 C12 1.2015(19) . ?
O8 C5 1.3859(17) . ?
O8 C14 1.4381(15) . ?
O9 C21 1.4053(16) . ?
O9 C15 1.4337(16) . ?
O10 C17 1.4205(18) . ?
O10 C16 1.4294(17) . ?
O11 C18 1.4223(16) . ?
O11 C17 1.4234(19) . ?
O12 C19 1.4307(16) . ?
O12 C20 1.4322(17) . ?
O13 C21 1.4152(15) . ?
O13 C20 1.4368(17) . ?
C1 C6 1.5205(18) . ?
C1 C2 1.5395(19) . ?
C1 C5 1.5407(17) . ?
C2 C3 1.5214(17) . ?
C3 C4 1.5222(17) . ?
C4 C11 1.5076(18) . ?
C7 C8 1.489(2) . ?
C9 C10 1.499(2) . ?
C12 C13 1.4959(19) . ?
C14 C15 1.5114(19) . ?
C15 C16 1.5184(18) . ?
C16 C18 1.544(2) . ?
C17 C22 1.514(2) . ?
C17 C23 1.515(2) . ?
C18 C19 1.5199(19) . ?
C19 C21 1.5370(19) . ?
C20 C25 1.509(2) . ?
C20 C24 1.5187(19) . ?

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
C4 O1 C5 112.49(10) . . ?
C7 O2 C2 117.42(11) . . ?
C9 O4 C3 117.78(11) . . ?
C12 O6 C11 115.67(11) . . ?
C5 O8 C14 114.70(10) . . ?
C21 O9 C15 113.49(10) . . ?
C17 O10 C16 108.99(11) . . ?
C18 O11 C17 106.91(11) . . ?
C19 O12 C20 105.42(10) . . ?
C21 O13 C20 109.88(10) . . ?
C6 C1 C2 110.29(10) . . ?
C6 C1 C5 111.17(11) . . ?
C2 C1 C5 110.77(10) . . ?
O2 C2 C3 105.92(10) . . ?
O2 C2 C1 108.99(10) . . ?
C3 C2 C1 112.61(10) . . ?
O4 C3 C2 107.82(10) . . ?
O4 C3 C4 108.66(10) . . ?
C2 C3 C4 109.53(11) . . ?
O1 C4 C11 107.04(11) . . ?
O1 C4 C3 106.41(10) . . ?
C11 C4 C3 112.23(11) . . ?
O8 C5 O1 106.82(10) . . ?
O8 C5 C1 107.89(10) . . ?
O1 C5 C1 109.27(10) . . ?
F1 C6 F2 106.80(12) . . ?
F1 C6 F3 106.13(12) . . ?
F2 C6 F3 106.22(12) . . ?
F1 C6 C1 113.35(11) . . ?
F2 C6 C1 111.89(11) . . ?
F3 C6 C1 111.98(12) . . ?
O3 C7 O2 122.98(13) . . ?
O3 C7 C8 126.61(13) . . ?
O2 C7 C8 110.41(13) . . ?
O5 C9 O4 123.85(14) . . ?
O5 C9 C10 125.73(15) . . ?
O4 C9 C10 110.41(14) . . ?
O6 C11 C4 106.42(11) . . ?
O7 C12 O6 122.48(12) . . ?
O7 C12 C13 126.78(12) . . ?
O6 C12 C13 110.74(12) . . ?
O8 C14 C15 111.93(10) . . ?
O9 C15 C14 107.57(11) . . ?
O9 C15 C16 109.67(10) . . ?
C14 C15 C16 111.36(10) . . ?
O10 C16 C15 109.28(11) . . ?
O10 C16 C18 104.25(11) . . ?
C15 C16 C18 111.74(11) . . ?
O10 C17 O11 105.22(10) . . ?
O10 C17 C22 109.03(14) . . ?
O11 C17 C22 108.15(13) . . ?
O10 C17 C23 110.67(13) . . ?
O11 C17 C23 110.68(13) . . ?
C22 C17 C23 112.78(13) . . ?
O11 C18 C19 106.42(11) . . ?
O11 C18 C16 104.04(11) . . ?
C19 C18 C16 114.35(11) . . ?
O12 C19 C18 109.11(11) . . ?
O12 C19 C21 103.40(10) . . ?
C18 C19 C21 113.76(11) . . ?
O12 C20 O13 104.91(10) . . ?
O12 C20 C25 109.18(11) . . ?
O13 C20 C25 109.31(12) . . ?
O12 C20 C24 110.49(12) . . ?
O13 C20 C24 109.58(11) . . ?
C25 C20 C24 113.05(11) . . ?
O9 C21 O13 110.36(10) . . ?
O9 C21 C19 114.55(11) . . ?
O13 C21 C19 103.88(10) . . ?

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
C7 O2 C2 C3 117.28(12) . . . . ?
C7 O2 C2 C1 -121.32(12) . . . . ?
C6 C1 C2 O2 73.84(13) . . . . ?
C5 C1 C2 O2 -162.66(10) . . . . ?
C6 C1 C2 C3 -168.93(11) . . . . ?
C5 C1 C2 C3 -45.43(14) . . . . ?
C9 O4 C3 C2 109.60(12) . . . . ?
C9 O4 C3 C4 -131.77(11) . . . . ?
O2 C2 C3 O4 -71.80(12) . . . . ?
C1 C2 C3 O4 169.16(10) . . . . ?
O2 C2 C3 C4 170.12(10) . . . . ?
C1 C2 C3 C4 51.08(14) . . . . ?
C5 O1 C4 C11 -169.24(10) . . . . ?
C5 O1 C4 C3 70.58(12) . . . . ?
O4 C3 C4 O1 -178.53(10) . . . . ?
C2 C3 C4 O1 -60.98(13) . . . . ?
O4 C3 C4 C11 64.70(14) . . . . ?
C2 C3 C4 C11 -177.75(12) . . . . ?
C14 O8 C5 O1 -66.87(13) . . . . ?
C14 O8 C5 C1 175.74(10) . . . . ?
C4 O1 C5 O8 178.21(9) . . . . ?
C4 O1 C5 C1 -65.31(13) . . . . ?
C6 C1 C5 O8 -71.16(13) . . . . ?
C2 C1 C5 O8 165.85(10) . . . . ?
C6 C1 C5 O1 173.05(11) . . . . ?
C2 C1 C5 O1 50.06(14) . . . . ?
C2 C1 C6 F1 -176.99(11) . . . . ?
C5 C1 C6 F1 59.74(16) . . . . ?
C2 C1 C6 F2 62.17(15) . . . . ?
C5 C1 C6 F2 -61.10(15) . . . . ?
C2 C1 C6 F3 -56.95(15) . . . . ?
C5 C1 C6 F3 179.78(12) . . . . ?
C2 O2 C7 O3 3.8(2) . . . . ?
C2 O2 C7 C8 -176.32(12) . . . . ?
C3 O4 C9 O5 -1.1(2) . . . . ?
C3 O4 C9 C10 178.00(12) . . . . ?
C12 O6 C11 C4 -163.80(12) . . . . ?
O1 C4 C11 O6 73.28(14) . . . . ?
C3 C4 C11 O6 -170.33(12) . . . . ?
C11 O6 C12 O7 1.5(2) . . . . ?
C11 O6 C12 C13 -177.96(12) . . . . ?
C5 O8 C14 C15 -95.47(13) . . . . ?
C21 O9 C15 C14 -168.53(10) . . . . ?
C21 O9 C15 C16 70.21(13) . . . . ?
O8 C14 C15 O9 78.91(13) . . . . ?
O8 C14 C15 C16 -160.89(11) . . . . ?
C17 O10 C16 C15 -127.87(12) . . . . ?
C17 O10 C16 C18 -8.29(14) . . . . ?
O9 C15 C16 O10 70.94(13) . . . . ?
C14 C15 C16 O10 -48.02(14) . . . . ?
O9 C15 C16 C18 -43.91(14) . . . . ?
C14 C15 C16 C18 -162.87(11) . . . . ?
C16 O10 C17 O11 25.69(15) . . . . ?
C16 O10 C17 C22 141.51(12) . . . . ?
C16 O10 C17 C23 -93.90(14) . . . . ?
C18 O11 C17 O10 -33.76(14) . . . . ?
C18 O11 C17 C22 -150.18(13) . . . . ?
C18 O11 C17 C23 85.82(14) . . . . ?
C17 O11 C18 C19 149.05(11) . . . . ?
C17 O11 C18 C16 27.94(13) . . . . ?
O10 C16 C18 O11 -11.98(13) . . . . ?
C15 C16 C18 O11 105.92(12) . . . . ?
O10 C16 C18 C19 -127.64(11) . . . . ?
C15 C16 C18 C19 -9.74(16) . . . . ?
C20 O12 C19 C18 156.18(11) . . . . ?
C20 O12 C19 C21 34.79(13) . . . . ?
O11 C18 C19 O12 173.13(10) . . . . ?
C16 C18 C19 O12 -72.60(14) . . . . ?
O11 C18 C19 C21 -72.00(14) . . . . ?
C16 C18 C19 C21 42.26(15) . . . . ?
C19 O12 C20 O13 -33.78(13) . . . . ?
C19 O12 C20 C25 -150.84(11) . . . . ?
C19 O12 C20 C24 84.23(13) . . . . ?
C21 O13 C20 O12 18.86(14) . . . . ?
C21 O13 C20 C25 135.83(11) . . . . ?
C21 O13 C20 C24 -99.77(13) . . . . ?
C15 O9 C21 O13 81.44(13) . . . . ?
C15 O9 C21 C19 -35.36(14) . . . . ?
C20 O13 C21 O9 -120.79(11) . . . . ?
C20 O13 C21 C19 2.46(13) . . . . ?
O12 C19 C21 O9 97.67(12) . . . . ?
C18 C19 C21 O9 -20.53(15) . . . . ?
O12 C19 C21 O13 -22.79(13) . . . . ?
C18 C19 C21 O13 -140.99(11) . . . . ?

_refine_diff_density_max         0.344
_refine_diff_density_min         -0.198
_refine_diff_density_rms         0.045

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

data_mo_JMV05136_0m
_database_code_depnum_ccdc_archive 'CCDC 2128832'
loop_
_audit_author_name
_audit_author_address
'Jordi Mestre'
;URV
Spain
;
_audit_update_record             
;
2021-12-15 deposited with the CCDC.	2023-03-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H19 F3 O9'
_chemical_formula_weight         400.30
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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Trigonal
_space_group_IT_number           145
_symmetry_space_group_name_H-M   P3(2)
_space_group_name_Hall           'P 32'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z+2/3'
'-x+y, -x, z+1/3'

_cell_length_a                   10.2792(4)
_cell_length_b                   10.2792(4)
_cell_length_c                   15.3888(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     1408.17(12)
_cell_formula_units_Z            3
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2689
_cell_measurement_theta_min      2.64
_cell_measurement_theta_max      30.18

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.416
_exptl_crystal_F_000             624
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.20
_exptl_absorpt_coefficient_mu    0.135
_shelx_estimated_absorpt_T_min   0.948
_shelx_estimated_absorpt_T_max   0.974
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.926
_exptl_absorpt_correction_T_max  0.974
_exptl_absorpt_process_details   
; 
 SADABS Version 2008/1 Bruker-Nonius
 Blessing, Acta Cryst. (1995) A51 33-38
;
_exptl_special_details           
; 
 It should be noted that the esd's of the cell dimensions are probably too low;
 they should be multiplied by a factor of 2 to 10
;
_diffrn_ambient_temperature      100(2)
_diffrn_measurement_specimen_support 'magnetic support with MicroMount'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Microfocus source E025 IuS'
_diffrn_source_type              'Bruker APEX DUO'
_diffrn_source_power             50
_diffrn_source_current           0.6
_diffrn_source_size              '0.2 mm x 0.2 mm fine focus'
_diffrn_radiation_monochromator  'Quazar MX Multilayer Optics'
_diffrn_detector_type            '4K CCD area detector APEX II'
_diffrn_measurement_device_type  'APEX DUO Kappa 4-axis goniometer'
_diffrn_measurement_method       
;
 Fullsphere data collection, phi and omega scans
;
_diffrn_detector_area_resol_mean 512
_diffrn_reflns_number            5160
_diffrn_reflns_av_unetI/netI     0.0282
_diffrn_reflns_av_R_equivalents  0.0148
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.288
_diffrn_reflns_theta_max         30.522
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.600
_diffrn_reflns_point_group_measured_fraction_full 0.654
_reflns_number_total             3458
_reflns_number_gt                3154
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.214
_reflns_Friedel_fraction_max     0.211
_reflns_Friedel_fraction_full    0.310

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.

 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2 v2014.9-0'
_computing_cell_refinement       'Bruker APEX2 v2014.9-0'
_computing_data_reduction        'Bruker SAINT V7.60A'
_computing_structure_solution    Sir2011
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0459P)²+0.1020P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 550 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_chemical_absolute_configuration ad
_refine_ls_abs_structure_Flack   -0.2(4)
_refine_ls_number_reflns         3458
_refine_ls_number_parameters     248
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0375
_refine_ls_R_factor_gt           0.0326
_refine_ls_wR_factor_ref         0.0852
_refine_ls_wR_factor_gt          0.0819
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_restrained_S_all      1.053
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C -0.1349(2) 0.5614(2) 0.24883(13) 0.0249(4) Uani 1 1 d . . . . .
H1 H -0.2286 0.4646 0.2618 0.030 Uiso 1 1 calc R U . . .
C2 C -0.0794(2) 0.6560(2) 0.33176(12) 0.0231(3) Uani 1 1 d . . . . .
H2 H -0.0597 0.5963 0.3757 0.028 Uiso 1 1 calc R U . . .
C3 C 0.0699(2) 0.8000(2) 0.31430(11) 0.0198(3) Uani 1 1 d . . . . .
H3 H 0.0537 0.8679 0.2749 0.024 Uiso 1 1 calc R U . . .
C4 C 0.1819(2) 0.7622(2) 0.27407(11) 0.0207(3) Uani 1 1 d . . . . .
H4 H 0.2154 0.7130 0.3177 0.025 Uiso 1 1 calc R U . . .
C5 C 0.1157(2) 0.6627(2) 0.19420(12) 0.0242(4) Uani 1 1 d . . . . .
H5 H 0.0977 0.7202 0.1480 0.029 Uiso 1 1 calc R U . . .
C6 C -0.2578(2) 0.5654(2) 0.11837(13) 0.0245(4) Uani 1 1 d . . . . .
C7 C -0.2678(3) 0.6700(3) 0.05530(14) 0.0331(4) Uani 1 1 d . . . . .
H7A H -0.3365 0.6121 0.0081 0.050 Uiso 1 1 calc R U . . .
H7B H -0.1679 0.7379 0.0313 0.050 Uiso 1 1 calc R U . . .
H7C H -0.3055 0.7289 0.0850 0.050 Uiso 1 1 calc R U . . .
C8 C -0.1959(2) 0.6888(3) 0.36990(15) 0.0356(5) Uani 1 1 d . . . . .
C9 C 0.1428(2) 1.0097(2) 0.40935(14) 0.0284(4) Uani 1 1 d . . . . .
C10 C 0.2025(3) 1.0664(3) 0.49855(15) 0.0418(6) Uani 1 1 d . . . . .
H10A H 0.2191 1.1683 0.5054 0.063 Uiso 1 1 calc R U . . .
H10B H 0.2977 1.0676 0.5066 0.063 Uiso 1 1 calc R U . . .
H10C H 0.1297 1.0002 0.5420 0.063 Uiso 1 1 calc R U . . .
C11 C 0.4489(2) 0.9384(3) 0.26577(13) 0.0322(4) Uani 1 1 d . . . . .
C12 C 0.5568(3) 1.1020(3) 0.2485(2) 0.0471(6) Uani 1 1 d . . . . .
H12A H 0.5396 1.1633 0.2906 0.071 Uiso 1 1 calc R U . . .
H12B H 0.5410 1.1274 0.1896 0.071 Uiso 1 1 calc R U . . .
H12C H 0.6601 1.1217 0.2542 0.071 Uiso 1 1 calc R U . . .
C13 C 0.2143(3) 0.6059(3) 0.15827(14) 0.0330(4) Uani 1 1 d . . . . .
H13A H 0.1658 0.5409 0.1072 0.040 Uiso 1 1 calc R U . . .
H13B H 0.3121 0.6913 0.1398 0.040 Uiso 1 1 calc R U . . .
C14 C 0.3476(2) 0.4916(2) 0.20957(17) 0.0369(5) Uani 1 1 d . . . . .
C15 C 0.3596(3) 0.4023(3) 0.2813(2) 0.0553(8) Uani 1 1 d . . . . .
H15A H 0.4428 0.3840 0.2696 0.083 Uiso 1 1 calc R U . . .
H15B H 0.2656 0.3060 0.2858 0.083 Uiso 1 1 calc R U . . .
H15C H 0.3781 0.4576 0.3360 0.083 Uiso 1 1 calc R U . . .
F1 F -0.33142(15) 0.56455(19) 0.37193(10) 0.0498(4) Uani 1 1 d . . . . .
F2 F -0.21100(17) 0.79335(18) 0.32723(11) 0.0473(4) Uani 1 1 d . . . . .
F3 F -0.16246(17) 0.7360(2) 0.45263(9) 0.0520(4) Uani 1 1 d . . . . .
O1 O -0.02480(16) 0.53141(15) 0.21654(9) 0.0261(3) Uani 1 1 d . . . . .
O2 O -0.16737(15) 0.64530(15) 0.18674(9) 0.0247(3) Uani 1 1 d . . . . .
O3 O -0.31530(17) 0.43170(16) 0.11204(10) 0.0309(3) Uani 1 1 d . . . . .
O4 O 0.13298(15) 0.87428(15) 0.39582(8) 0.0231(3) Uani 1 1 d . . . . .
O5 O 0.1056(2) 1.0701(2) 0.35654(11) 0.0410(4) Uani 1 1 d . . . . .
O6 O 0.30659(15) 0.90635(16) 0.24788(9) 0.0263(3) Uani 1 1 d . . . . .
O7 O 0.47988(18) 0.8482(2) 0.29237(12) 0.0455(4) Uani 1 1 d . . . . .
O8 O 0.23644(17) 0.52202(17) 0.22533(10) 0.0325(3) Uani 1 1 d . . . . .
O9 O 0.42405(19) 0.5330(2) 0.14480(13) 0.0470(5) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O1 1.404(2) . ?
C1 O2 1.434(2) . ?
C1 C2 1.532(3) . ?
C2 C8 1.515(3) . ?
C2 C3 1.532(3) . ?
C3 O4 1.443(2) . ?
C3 C4 1.518(3) . ?
C4 O6 1.449(2) . ?
C4 C5 1.525(3) . ?
C5 O1 1.441(2) . ?
C5 C13 1.504(3) . ?
C6 O3 1.198(2) . ?
C6 O2 1.372(2) . ?
C6 C7 1.490(3) . ?
C8 F2 1.333(3) . ?
C8 F1 1.339(3) . ?
C8 F3 1.344(3) . ?
C9 O5 1.196(3) . ?
C9 O4 1.361(2) . ?
C9 C10 1.498(3) . ?
C11 O7 1.193(3) . ?
C11 O6 1.357(2) . ?
C11 C12 1.504(3) . ?
C13 O8 1.434(3) . ?
C14 O9 1.207(3) . ?
C14 O8 1.349(3) . ?
C14 C15 1.480(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 O2 110.60(15) . . ?
O1 C1 C2 110.43(15) . . ?
O2 C1 C2 107.35(15) . . ?
C8 C2 C3 112.04(17) . . ?
C8 C2 C1 112.26(16) . . ?
C3 C2 C1 110.03(15) . . ?
O4 C3 C4 107.01(13) . . ?
O4 C3 C2 109.07(14) . . ?
C4 C3 C2 110.27(15) . . ?
O6 C4 C3 104.38(14) . . ?
O6 C4 C5 109.37(15) . . ?
C3 C4 C5 111.07(15) . . ?
O1 C5 C13 106.19(16) . . ?
O1 C5 C4 109.77(14) . . ?
C13 C5 C4 113.31(16) . . ?
O3 C6 O2 123.17(18) . . ?
O3 C6 C7 127.04(19) . . ?
O2 C6 C7 109.77(17) . . ?
F2 C8 F1 107.16(18) . . ?
F2 C8 F3 106.7(2) . . ?
F1 C8 F3 106.16(18) . . ?
F2 C8 C2 114.33(18) . . ?
F1 C8 C2 111.0(2) . . ?
F3 C8 C2 111.05(17) . . ?
O5 C9 O4 123.24(19) . . ?
O5 C9 C10 126.60(19) . . ?
O4 C9 C10 110.15(18) . . ?
O7 C11 O6 123.7(2) . . ?
O7 C11 C12 126.5(2) . . ?
O6 C11 C12 109.8(2) . . ?
O8 C13 C5 107.98(16) . . ?
O9 C14 O8 123.0(2) . . ?
O9 C14 C15 126.4(2) . . ?
O8 C14 C15 110.6(2) . . ?
C1 O1 C5 114.81(14) . . ?
C6 O2 C1 116.29(15) . . ?
C9 O4 C3 117.30(15) . . ?
C11 O6 C4 119.12(15) . . ?
C14 O8 C13 114.68(18) . . ?

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 C8 -178.93(16) . . . . ?
O2 C1 C2 C8 60.4(2) . . . . ?
O1 C1 C2 C3 55.57(19) . . . . ?
O2 C1 C2 C3 -65.08(19) . . . . ?
C8 C2 C3 O4 64.20(19) . . . . ?
C1 C2 C3 O4 -170.17(15) . . . . ?
C8 C2 C3 C4 -178.56(15) . . . . ?
C1 C2 C3 C4 -52.93(19) . . . . ?
O4 C3 C4 O6 -70.74(16) . . . . ?
C2 C3 C4 O6 170.76(14) . . . . ?
O4 C3 C4 C5 171.50(14) . . . . ?
C2 C3 C4 C5 53.00(19) . . . . ?
O6 C4 C5 O1 -168.93(14) . . . . ?
C3 C4 C5 O1 -54.26(19) . . . . ?
O6 C4 C5 C13 72.5(2) . . . . ?
C3 C4 C5 C13 -172.79(16) . . . . ?
C3 C2 C8 F2 48.9(2) . . . . ?
C1 C2 C8 F2 -75.5(2) . . . . ?
C3 C2 C8 F1 170.26(16) . . . . ?
C1 C2 C8 F1 45.9(2) . . . . ?
C3 C2 C8 F3 -71.9(2) . . . . ?
C1 C2 C8 F3 163.72(18) . . . . ?
O1 C5 C13 O8 -61.6(2) . . . . ?
C4 C5 C13 O8 59.0(2) . . . . ?
O2 C1 O1 C5 58.5(2) . . . . ?
C2 C1 O1 C5 -60.17(19) . . . . ?
C13 C5 O1 C1 -177.90(15) . . . . ?
C4 C5 O1 C1 59.26(19) . . . . ?
O3 C6 O2 C1 4.4(3) . . . . ?
C7 C6 O2 C1 -174.11(16) . . . . ?
O1 C1 O2 C6 77.64(19) . . . . ?
C2 C1 O2 C6 -161.82(15) . . . . ?
O5 C9 O4 C3 -2.0(3) . . . . ?
C10 C9 O4 C3 176.89(18) . . . . ?
C4 C3 O4 C9 127.04(17) . . . . ?
C2 C3 O4 C9 -113.68(17) . . . . ?
O7 C11 O6 C4 9.7(3) . . . . ?
C12 C11 O6 C4 -169.29(19) . . . . ?
C3 C4 O6 C11 134.89(17) . . . . ?
C5 C4 O6 C11 -106.20(19) . . . . ?
O9 C14 O8 C13 0.9(3) . . . . ?
C15 C14 O8 C13 -178.79(19) . . . . ?
C5 C13 O8 C14 -166.33(17) . . . . ?

_refine_diff_density_max         0.226
_refine_diff_density_min         -0.226
_refine_diff_density_rms         0.047
