# Supplementary Information (SI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2025

####################################################################### 
# 
# 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_GoldsmithSK070621b
_database_code_depnum_ccdc_archive 'CCDC 2259450'
loop_
_audit_author_name
_audit_author_address
'Phani Raj Pokkuluri'
;Auburn University
United States of America
;
_audit_update_record             
;
2023-04-27 deposited with the CCDC.	2025-09-09 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C9 H9 F O3'
_chemical_formula_iupac          ?
_chemical_formula_weight         184.16

_chemical_melting_point          ?

_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                   18.7223(13)
_cell_length_b                   11.2619(7)
_cell_length_c                   8.6284(7)
_cell_angle_alpha                90
_cell_angle_beta                 109.598(3)
_cell_angle_gamma                90
_cell_volume                     1713.9(2)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9620
_cell_measurement_theta_min      2.3094
_cell_measurement_theta_max      30.5369
_cell_measurement_temperature    298.(2)

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.275
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.120
_exptl_crystal_density_diffrn    1.427
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             768

_exptl_absorpt_coefficient_mu    0.120
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
Krause, L., Herbst-Irmer, R., Sheldrick, G. M., Stalke, D. (2015).
"Comparison of silver and molybdenum microfocus X-ray sources for
single-crystal structure determination"
J. Appl. Cryst. 48, 3-10.
;
_exptl_absorpt_correction_T_min  0.87
_exptl_absorpt_correction_T_max  0.99

_exptl_special_details           
;
;

_diffrn_ambient_temperature      298.(2)

_diffrn_source                   'microfocus sealed tube'
_diffrn_source_type              'Incoatec I\mS 3.0'
_diffrn_source_power             0.07
_diffrn_source_current           1.4
_diffrn_source_voltage           50

_diffrn_radiation_probe          ?
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'multilayer mirror'

_diffrn_measurement_device       'κ--geometry diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'

_diffrn_detector_area_resol_mean 7.3910

_diffrn_reflns_number            23277
_diffrn_reflns_av_R_equivalents  0.0391
_diffrn_reflns_av_unetI/netI     0.0187
_diffrn_reflns_theta_min         2.15
_diffrn_reflns_theta_max         28.28
_diffrn_reflns_theta_full        25.24
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11

_refine_special_details          
;
;

_reflns_number_total             2133
_reflns_number_gt                1660
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0547
_refine_ls_R_factor_gt           0.0409
_refine_ls_wR_factor_gt          0.1161
_refine_ls_wR_factor_ref         0.1278
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_restrained_S_all      1.046
_refine_ls_number_reflns         2133
_refine_ls_number_parameters     120
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0690P)²+0.3868P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.236
_refine_diff_density_min         -0.206
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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

_computing_data_collection       
'Bruker Instrument Service, BIS, v6.2.6 (Bruker AXS Inc., 2017)'
_computing_cell_refinement       'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 994)'
_computing_publication_material  'APEX3 v2018.1-0 (Bruker AXS Inc., 2017)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F F1 0.25395(5) 0.29324(8) 0.76559(11) 0.0689(3) Uani d . . . 1 . .
C C1 0.30930(6) 0.27142(11) 0.70175(15) 0.0472(3) Uani d . . . 1 . .
O O1 0.52017(6) 0.28597(9) 0.47456(13) 0.0643(3) Uani d . . . 1 . .
O O2 0.40264(6) 0.02143(7) 0.58002(13) 0.0593(3) Uani d . . . 1 . .
C C2 0.32470(6) 0.15564(10) 0.67614(15) 0.0467(3) Uani d . . . 1 . .
H H2 0.297474 0.093863 0.701262 0.056 Uiso calc U . R 1 . .
C C4 0.42226(6) 0.22778(10) 0.57497(13) 0.0433(3) Uani d . . . 1 . .
O O3 0.32425(5) 0.47821(7) 0.69774(13) 0.0593(3) Uani d . . . 1 . .
C C3 0.38239(6) 0.13275(11) 0.61128(13) 0.0443(3) Uani d . . . 1 . .
C C5 0.40383(6) 0.34425(10) 0.60157(14) 0.0445(3) Uani d . . . 1 . .
H H5 0.430304 0.406702 0.57562 0.053 Uiso calc U . R 1 . .
C C6 0.34712(6) 0.36861(10) 0.66559(14) 0.0454(3) Uani d . . . 1 . .
C C7 0.48527(7) 0.20782(11) 0.51210(16) 0.0511(3) Uani d . . . 1 . .
H H7 0.499009 0.129801 0.500651 0.061 Uiso calc U . R 1 . .
C C8 0.36460(9) 0.57659(12) 0.6640(2) 0.0664(4) Uani d . . . 1 . .
H H8A 0.359608 0.576452 0.54961 0.1 Uiso calc U . R 1 . .
H H8B 0.41721 0.570504 0.729685 0.1 Uiso calc U . R 1 . .
H H8C 0.344151 0.649096 0.690091 0.1 Uiso calc U . R 1 . .
C C9 0.36323(9) -0.07607(12) 0.61841(19) 0.0631(4) Uani d . . . 1 . .
H H9A 0.310492 -0.071454 0.553157 0.095 Uiso calc U . R 1 . .
H H9B 0.368547 -0.073462 0.732961 0.095 Uiso calc U . R 1 . .
H H9C 0.384046 -0.14909 0.595034 0.095 Uiso calc U . R 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
F1 C1 . 1.3493(13) ?
C1 C2 . 1.3692(17) ?
C1 C6 . 1.3946(16) ?
O1 C7 . 1.2036(15) ?
O2 C3 . 1.3627(14) ?
O2 C9 . 1.4226(16) ?
C2 C3 . 1.3971(15) ?
C4 C5 . 1.3948(16) ?
C4 C3 . 1.3991(15) ?
C4 C7 . 1.4717(15) ?
O3 C6 . 1.3651(14) ?
O3 C8 . 1.4248(17) ?
C5 C6 . 1.3788(16) ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
F1 C1 C2 . . 118.13(11) ?
F1 C1 C6 . . 117.74(11) ?
C2 C1 C6 . . 124.14(10) ?
C3 O2 C9 . . 117.62(10) ?
C1 C2 C3 . . 118.24(10) ?
C5 C4 C3 . . 120.16(10) ?
C5 C4 C7 . . 118.52(10) ?
C3 C4 C7 . . 121.30(10) ?
C6 O3 C8 . . 115.96(10) ?
O2 C3 C2 . . 123.56(10) ?
O2 C3 C4 . . 117.05(9) ?
C2 C3 C4 . . 119.40(11) ?
C6 C5 C4 . . 121.28(11) ?
O3 C6 C5 . . 126.68(10) ?
O3 C6 C1 . . 116.54(10) ?
C5 C6 C1 . . 116.77(11) ?
O1 C7 C4 . . 124.20(12) ?

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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
F1 C1 C2 C3 . . . . -179.50(10) ?
C6 C1 C2 C3 . . . . 0.68(19) ?
C9 O2 C3 C2 . . . . -1.00(18) ?
C9 O2 C3 C4 . . . . 179.19(11) ?
C1 C2 C3 O2 . . . . -179.77(11) ?
C1 C2 C3 C4 . . . . 0.04(17) ?
C5 C4 C3 O2 . . . . 179.06(10) ?
C7 C4 C3 O2 . . . . -2.40(17) ?
C5 C4 C3 C2 . . . . -0.76(17) ?
C7 C4 C3 C2 . . . . 177.77(10) ?
C3 C4 C5 C6 . . . . 0.82(18) ?
C7 C4 C5 C6 . . . . -177.75(10) ?
C8 O3 C6 C5 . . . . -1.29(19) ?
C8 O3 C6 C1 . . . . 178.51(11) ?
C4 C5 C6 O3 . . . . 179.66(11) ?
C4 C5 C6 C1 . . . . -0.14(18) ?
F1 C1 C6 O3 . . . . -0.28(17) ?
C2 C1 C6 O3 . . . . 179.55(11) ?
F1 C1 C6 C5 . . . . 179.55(10) ?
C2 C1 C6 C5 . . . . -0.63(19) ?
C5 C4 C7 O1 . . . . -3.57(19) ?
C3 C4 C7 O1 . . . . 177.87(12) ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
C8 H8C F1 4_556 0.96 2.57 3.4860(17) 158.7 ?
C9 H9C O1 5_656 0.96 2.58 3.4889(18) 157.3 ?

####################################################################### 
# 
# 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_GoldsmithSK091421
_database_code_depnum_ccdc_archive 'CCDC 2259451'
loop_
_audit_author_name
_audit_author_address
'Phani Raj Pokkuluri'
;Auburn University
United States of America
;
_audit_update_record             
;
2023-04-27 deposited with the CCDC.	2025-09-09 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C7 H5 F O3'
_chemical_formula_iupac          ?
_chemical_formula_weight         156.11

_chemical_melting_point          ?

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.6681(5)
_cell_length_b                   8.3643(6)
_cell_length_c                   11.4816(8)
_cell_angle_alpha                76.068(2)
_cell_angle_beta                 77.790(2)
_cell_angle_gamma                64.382(2)
_cell_volume                     639.61(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9785
_cell_measurement_theta_min      2.7403
_cell_measurement_theta_max      36.3943
_cell_measurement_temperature    110.(2)

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.140
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.100
_exptl_crystal_density_diffrn    1.621
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             320

_exptl_absorpt_coefficient_mu    0.145
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
Krause, L., Herbst-Irmer, R., Sheldrick, G. M., Stalke, D. (2015).
"Comparison of silver and molybdenum microfocus X-ray sources for
single-crystal structure determination"
J. Appl. Cryst. 48, 3-10.
;
_exptl_absorpt_correction_T_min  0.93
_exptl_absorpt_correction_T_max  0.99

_exptl_special_details           
;
;

_diffrn_ambient_temperature      110.(2)

_diffrn_source                   'microfocus sealed tube'
_diffrn_source_type              'Incoatec I\mS 3.0'
_diffrn_source_power             0.07
_diffrn_source_current           1.4
_diffrn_source_voltage           50

_diffrn_radiation_probe          ?
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'multilayer mirror'

_diffrn_measurement_device       'κ--geometry diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'

_diffrn_detector_area_resol_mean 7.3910

_diffrn_reflns_number            46412
_diffrn_reflns_av_R_equivalents  0.0326
_diffrn_reflns_av_unetI/netI     0.0194
_diffrn_reflns_theta_min         2.74
_diffrn_reflns_theta_max         36.40
_diffrn_reflns_theta_full        25.24
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19

_refine_special_details          
;
;

_reflns_number_total             6236
_reflns_number_gt                5451
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0396
_refine_ls_R_factor_gt           0.0344
_refine_ls_wR_factor_gt          0.1039
_refine_ls_wR_factor_ref         0.1086
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_restrained_S_all      1.041
_refine_ls_number_reflns         6236
_refine_ls_number_parameters     203
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0587P)²+0.1221P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.531
_refine_diff_density_min         -0.255
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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

_computing_data_collection       
'Bruker Instrument Service, BIS, v6.2.6 (Bruker AXS Inc., 2017)'
_computing_cell_refinement       'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 994)'
_computing_publication_material  'APEX3 v2018.1-0 (Bruker AXS Inc., 2017)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F F1 0.81802(7) 1.41549(6) -0.08549(4) 0.02077(9) Uani d . . . 1 . .
C C1 0.77532(9) 1.27058(8) -0.03914(5) 0.01426(10) Uani d . . . 1 . .
O O1 0.62505(8) 1.39266(7) 0.14622(5) 0.01961(10) Uani d . . . 1 . .
H H1 0.662061 1.47339 0.106798 0.029 Uiso calc U . R 1 . .
F F2 0.67505(7) 0.76829(6) 0.58181(4) 0.02429(10) Uani d . . . 1 . .
C C2 0.67775(9) 1.26227(8) 0.07901(5) 0.01390(9) Uani d . . . 1 . .
O O2 0.84992(8) 0.85625(7) -0.12609(5) 0.02040(10) Uani d . . . 1 . .
H H2 0.81958 0.771773 -0.085991 0.031 Uiso calc U . R 1 . .
O O3 0.71016(8) 0.68400(7) 0.06305(5) 0.02031(10) Uani d . . . 1 . .
C C3 0.63778(9) 1.11178(8) 0.12682(5) 0.01394(10) Uani d . . . 1 . .
H H3 0.570743 1.101934 0.206121 0.017 Uiso calc U . R 1 . .
C C4 0.69479(8) 0.97300(8) 0.05994(5) 0.01313(9) Uani d . . . 1 . .
C C7 0.65464(9) 0.81512(8) 0.11471(6) 0.01569(10) Uani d . . . 1 . .
H H7 0.583177 0.812029 0.193052 0.019 Uiso calc U . R 1 . .
C C6 0.83145(9) 1.13907(8) -0.10870(5) 0.01483(10) Uani d . . . 1 . .
H H6 0.895275 1.15174 -0.188713 0.018 Uiso calc U . R 1 . .
C C5 0.79218(9) 0.98694(8) -0.05863(5) 0.01402(9) Uani d . . . 1 . .
O O101 0.67666(8) 0.19272(7) 0.63111(5) 0.02137(10) Uani d . . . 1 . .
H H101 0.703206 0.111919 0.590699 0.032 Uiso calc U . R 1 . .
C C101 0.71851(9) 0.61968(8) 0.53558(6) 0.01627(10) Uani d . . . 1 . .
O O102 0.84061(8) 0.75814(7) 0.34389(5) 0.02070(10) Uani d . . . 1 . .
H H102 0.819906 0.835029 0.386287 0.031 Uiso calc U . R 1 . .
C C102 0.80367(9) 0.61794(8) 0.41460(5) 0.01520(10) Uani d . . . 1 . .
O O103 0.80717(9) 0.03727(7) 0.44014(5) 0.02324(10) Uani d . . . 1 . .
C C104 0.80541(9) 0.32075(8) 0.43856(5) 0.01460(10) Uani d . . . 1 . .
C C105 0.71961(9) 0.32854(8) 0.55988(5) 0.01542(10) Uani d . . . 1 . .
C C106 0.67714(9) 0.48041(9) 0.60869(5) 0.01717(11) Uani d . . . 1 . .
H H106 0.621046 0.487743 0.690371 0.021 Uiso calc U . R 1 . .
C C107 0.84596(10) 0.16722(9) 0.38453(6) 0.01804(11) Uani d . . . 1 . .
H H107 0.904794 0.165598 0.302982 0.022 Uiso calc U . R 1 . .
C C103 0.84681(9) 0.46593(8) 0.36774(5) 0.01548(10) Uani d . . . 1 . .
H H103 0.90535 0.459107 0.286429 0.019 Uiso calc U . R 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
F1 C1 . 1.3484(7) ?
C1 C6 . 1.3788(8) ?
C1 C2 . 1.4054(8) ?
O1 C2 . 1.3567(7) ?
F2 C101 . 1.3500(7) ?
C2 C3 . 1.3819(8) ?
O2 C5 . 1.3546(7) ?
O3 C7 . 1.2404(8) ?
C3 C4 . 1.4059(8) ?
C4 C5 . 1.4120(8) ?
C4 C7 . 1.4505(8) ?
C6 C5 . 1.3951(8) ?
O101 C105 . 1.3529(8) ?
C101 C106 . 1.3778(9) ?
C101 C102 . 1.4050(9) ?
O102 C102 . 1.3587(7) ?
C102 C103 . 1.3805(8) ?
O103 C107 . 1.2420(8) ?
C104 C103 . 1.4090(8) ?
C104 C105 . 1.4129(9) ?
C104 C107 . 1.4448(9) ?
C105 C106 . 1.3935(9) ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
F1 C1 C6 . . 118.72(5) ?
F1 C1 C2 . . 117.33(5) ?
C6 C1 C2 . . 123.95(5) ?
O1 C2 C3 . . 119.97(5) ?
O1 C2 C1 . . 122.99(5) ?
C3 C2 C1 . . 117.04(5) ?
C2 C3 C4 . . 121.02(5) ?
C3 C4 C5 . . 120.10(5) ?
C3 C4 C7 . . 119.26(5) ?
C5 C4 C7 . . 120.63(5) ?
O3 C7 C4 . . 122.43(6) ?
C1 C6 C5 . . 118.34(5) ?
O2 C5 C6 . . 118.45(5) ?
O2 C5 C4 . . 122.01(5) ?
C6 C5 C4 . . 119.54(5) ?
F2 C101 C106 . . 118.65(5) ?
F2 C101 C102 . . 117.18(6) ?
C106 C101 C102 . . 124.17(6) ?
O102 C102 C103 . . 120.10(5) ?
O102 C102 C101 . . 123.02(6) ?
C103 C102 C101 . . 116.87(5) ?
C103 C104 C105 . . 120.08(5) ?
C103 C104 C107 . . 119.24(5) ?
C105 C104 C107 . . 120.65(6) ?
O101 C105 C106 . . 118.41(5) ?
O101 C105 C104 . . 122.14(6) ?
C106 C105 C104 . . 119.45(5) ?
C101 C106 C105 . . 118.36(5) ?
O103 C107 C104 . . 122.80(6) ?
C102 C103 C104 . . 121.06(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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
F1 C1 C2 O1 . . . . 0.46(9) ?
C6 C1 C2 O1 . . . . 179.51(6) ?
F1 C1 C2 C3 . . . . -178.78(5) ?
C6 C1 C2 C3 . . . . 0.28(9) ?
O1 C2 C3 C4 . . . . -178.57(5) ?
C1 C2 C3 C4 . . . . 0.69(9) ?
C2 C3 C4 C5 . . . . -0.86(9) ?
C2 C3 C4 C7 . . . . 178.35(5) ?
C3 C4 C7 O3 . . . . -176.10(6) ?
C5 C4 C7 O3 . . . . 3.11(10) ?
F1 C1 C6 C5 . . . . 178.00(5) ?
C2 C1 C6 C5 . . . . -1.04(9) ?
C1 C6 C5 O2 . . . . -178.98(5) ?
C1 C6 C5 C4 . . . . 0.84(9) ?
C3 C4 C5 O2 . . . . 179.88(5) ?
C7 C4 C5 O2 . . . . 0.68(9) ?
C3 C4 C5 C6 . . . . 0.07(9) ?
C7 C4 C5 C6 . . . . -179.13(5) ?
F2 C101 C102 O102 . . . . -0.82(9) ?
C106 C101 C102 O102 . . . . 179.09(6) ?
F2 C101 C102 C103 . . . . -179.68(5) ?
C106 C101 C102 C103 . . . . 0.23(10) ?
C103 C104 C105 O101 . . . . 179.76(6) ?
C107 C104 C105 O101 . . . . 1.74(9) ?
C103 C104 C105 C106 . . . . -0.22(9) ?
C107 C104 C105 C106 . . . . -178.24(6) ?
F2 C101 C106 C105 . . . . 179.03(6) ?
C102 C101 C106 C105 . . . . -0.88(10) ?
O101 C105 C106 C101 . . . . -179.13(6) ?
C104 C105 C106 C101 . . . . 0.84(9) ?
C103 C104 C107 O103 . . . . -177.48(6) ?
C105 C104 C107 O103 . . . . 0.56(10) ?
O102 C102 C103 C104 . . . . -178.46(6) ?
C101 C102 C103 C104 . . . . 0.44(9) ?
C105 C104 C103 C102 . . . . -0.44(9) ?
C107 C104 C103 C102 . . . . 177.60(6) ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
O1 H1 F1 . 0.84 2.33 2.7637(7) 112.5 ?
O1 H1 O3 1_565 0.84 1.88 2.6957(7) 162.2 ?
O2 H2 O3 . 0.84 1.87 2.6047(7) 145.5 ?
C7 H7 O101 2_666 0.95 2.52 3.4482(8) 164.0 ?
C6 H6 O102 2_775 0.95 2.64 3.4977(8) 149.8 ?
O101 H101 O103 . 0.84 1.88 2.6114(8) 145.4 ?
O102 H102 F2 . 0.84 2.34 2.7628(7) 111.9 ?
O102 H102 O103 1_565 0.84 1.89 2.7098(8) 163.3 ?
C106 H106 O1 2_676 0.95 2.42 3.3118(8) 156.3 ?
C107 H107 O2 2_765 0.95 2.44 3.3525(8) 160.6 ?

