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

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

data_gol1574
_database_code_depnum_ccdc_archive 'CCDC 2169359'
loop_
_audit_author_name
_audit_author_address
'Kyrill Yu.  Suponitsky'
;A N Nesmeyanov Institute of Organoelement Compounds, Moscow, Russia
Russia
;
_audit_update_record             
;
2022-04-28 deposited with the CCDC.	2022-08-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H11 F3 O'
_chemical_formula_sum            'C12 H11 F3 O'
_chemical_formula_weight         228.21

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           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   9.7631(12)
_cell_length_b                   10.2430(14)
_cell_length_c                   10.4343(13)
_cell_angle_alpha                90
_cell_angle_beta                 92.382(4)
_cell_angle_gamma                90
_cell_volume                     1042.6(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    2142
_cell_measurement_theta_min      2.79
_cell_measurement_theta_max      22.37

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.454
_exptl_crystal_F_000             472
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.01
_exptl_absorpt_coefficient_mu    0.127
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9722
_diffrn_reflns_av_unetI/netI     0.0469
_diffrn_reflns_av_R_equivalents  0.0497
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.088
_diffrn_reflns_theta_max         26.390
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2108
_reflns_number_gt                1414
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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       'APEX (Bruker, 2014)'
_computing_cell_refinement       'SAINT (Bruker, 2014)'
_computing_data_reduction        'SAINT (Bruker, 2014)'
_computing_structure_solution    'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_publication_material  
'SHELXL-2014/6 (Sheldrick, 2014) and PLATON (Spek, 2009)'
_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)+(0.0664P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2108
_refine_ls_number_parameters     147
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0753
_refine_ls_R_factor_gt           0.0408
_refine_ls_wR_factor_ref         0.1141
_refine_ls_wR_factor_gt          0.0999
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_restrained_S_all      1.010
_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 0.86556(11) 0.05205(11) 0.97243(11) 0.0359(3) Uani 1 1 d . . . . .
F2 F 0.71661(11) 0.02777(11) 1.11656(10) 0.0359(3) Uani 1 1 d . . . . .
F3 F 0.66540(12) 0.13762(11) 0.94558(11) 0.0398(3) Uani 1 1 d . . . . .
O1 O 0.53580(13) -0.31541(12) 0.85306(11) 0.0282(3) Uani 1 1 d . . . . .
C1 C 0.65191(19) -0.32795(18) 0.93193(16) 0.0241(4) Uani 1 1 d . . . . .
C2 C 0.68275(19) -0.45068(18) 0.98020(17) 0.0261(4) Uani 1 1 d . . . . .
H2A H 0.6274 -0.5230 0.9541 0.031 Uiso 1 1 calc R U . . .
C3 C 0.7936(2) -0.46997(18) 1.06637(17) 0.0265(4) Uani 1 1 d . . . . .
C4 C 0.87582(19) -0.36270(19) 1.10326(17) 0.0256(4) Uani 1 1 d . . . . .
C5 C 0.84161(18) -0.24026(19) 1.05580(16) 0.0252(4) Uani 1 1 d . . . . .
H5A H 0.8967 -0.1677 1.0818 0.030 Uiso 1 1 calc R U . . .
C6 C 0.72915(18) -0.21934(18) 0.97106(15) 0.0228(4) Uani 1 1 d . . . . .
C7 C 0.68022(18) -0.09094(18) 0.92436(17) 0.0242(4) Uani 1 1 d . . . . .
C8 C 0.58854(19) -0.08506(19) 0.82627(18) 0.0271(5) Uani 1 1 d . . . . .
H8A H 0.5558 -0.0029 0.7959 0.033 Uiso 1 1 calc R U . . .
C9 C 0.5376(2) -0.20790(19) 0.76458(17) 0.0284(5) Uani 1 1 d . . . . .
H9A H 0.4437 -0.1934 0.7279 0.034 Uiso 1 1 calc R U . . .
H9B H 0.5970 -0.2305 0.6932 0.034 Uiso 1 1 calc R U . . .
C10 C 0.8233(2) -0.60498(19) 1.11786(19) 0.0346(5) Uani 1 1 d . . . . .
H10A H 0.7474 -0.6635 1.0927 0.052 Uiso 1 1 calc R U . . .
H10B H 0.8335 -0.6016 1.2116 0.052 Uiso 1 1 calc R U . . .
H10C H 0.9082 -0.6377 1.0827 0.052 Uiso 1 1 calc R U . . .
C11 C 0.9982(2) -0.3801(2) 1.19498(19) 0.0340(5) Uani 1 1 d . . . . .
H11A H 1.0521 -0.2993 1.1984 0.051 Uiso 1 1 calc R U . . .
H11B H 1.0553 -0.4518 1.1653 0.051 Uiso 1 1 calc R U . . .
H11C H 0.9667 -0.4003 1.2807 0.051 Uiso 1 1 calc R U . . .
C12 C 0.73080(19) 0.03068(19) 0.98918(18) 0.0284(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
F1 C12 1.352(2) . ?
F2 C12 1.342(2) . ?
F3 C12 1.338(2) . ?
O1 C1 1.379(2) . ?
O1 C9 1.438(2) . ?
C1 C2 1.383(3) . ?
C1 C6 1.395(2) . ?
C2 C3 1.392(3) . ?
C2 H2A 0.9500 . ?
C3 C4 1.405(3) . ?
C3 C10 1.507(3) . ?
C4 C5 1.384(3) . ?
C4 C11 1.510(3) . ?
C5 C6 1.397(2) . ?
C5 H5A 0.9500 . ?
C6 C7 1.475(3) . ?
C7 C8 1.333(3) . ?
C7 C12 1.492(3) . ?
C8 C9 1.489(3) . ?
C8 H8A 0.9500 . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 C9 115.03(14) . . ?
O1 C1 C2 117.60(16) . . ?
O1 C1 C6 121.41(16) . . ?
C2 C1 C6 120.76(17) . . ?
C1 C2 C3 121.07(17) . . ?
C1 C2 H2A 119.5 . . ?
C3 C2 H2A 119.5 . . ?
C2 C3 C4 119.07(17) . . ?
C2 C3 C10 119.55(17) . . ?
C4 C3 C10 121.38(17) . . ?
C5 C4 C3 118.94(17) . . ?
C5 C4 C11 120.41(17) . . ?
C3 C4 C11 120.64(17) . . ?
C4 C5 C6 122.47(17) . . ?
C4 C5 H5A 118.8 . . ?
C6 C5 H5A 118.8 . . ?
C1 C6 C5 117.63(17) . . ?
C1 C6 C7 116.78(16) . . ?
C5 C6 C7 125.51(17) . . ?
C8 C7 C6 119.46(17) . . ?
C8 C7 C12 120.64(18) . . ?
C6 C7 C12 119.88(16) . . ?
C7 C8 C9 119.69(18) . . ?
C7 C8 H8A 120.2 . . ?
C9 C8 H8A 120.2 . . ?
O1 C9 C8 112.47(15) . . ?
O1 C9 H9A 109.1 . . ?
C8 C9 H9A 109.1 . . ?
O1 C9 H9B 109.1 . . ?
C8 C9 H9B 109.1 . . ?
H9A C9 H9B 107.8 . . ?
C3 C10 H10A 109.5 . . ?
C3 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C3 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C4 C11 H11A 109.5 . . ?
C4 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C4 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
F3 C12 F2 106.70(15) . . ?
F3 C12 F1 106.06(15) . . ?
F2 C12 F1 105.82(15) . . ?
F3 C12 C7 112.65(16) . . ?
F2 C12 C7 112.62(15) . . ?
F1 C12 C7 112.47(15) . . ?

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
C9 O1 C1 C2 -154.71(16) . . . . ?
C9 O1 C1 C6 30.8(2) . . . . ?
O1 C1 C2 C3 -176.21(16) . . . . ?
C6 C1 C2 C3 -1.7(3) . . . . ?
C1 C2 C3 C4 -0.7(3) . . . . ?
C1 C2 C3 C10 179.45(16) . . . . ?
C2 C3 C4 C5 2.0(3) . . . . ?
C10 C3 C4 C5 -178.21(16) . . . . ?
C2 C3 C4 C11 -179.07(17) . . . . ?
C10 C3 C4 C11 0.8(3) . . . . ?
C3 C4 C5 C6 -0.9(3) . . . . ?
C11 C4 C5 C6 -179.82(16) . . . . ?
O1 C1 C6 C5 177.07(15) . . . . ?
C2 C1 C6 C5 2.8(3) . . . . ?
O1 C1 C6 C7 0.2(2) . . . . ?
C2 C1 C6 C7 -174.08(16) . . . . ?
C4 C5 C6 C1 -1.5(3) . . . . ?
C4 C5 C6 C7 175.04(16) . . . . ?
C1 C6 C7 C8 -15.8(2) . . . . ?
C5 C6 C7 C8 167.59(17) . . . . ?
C1 C6 C7 C12 162.58(16) . . . . ?
C5 C6 C7 C12 -14.0(3) . . . . ?
C6 C7 C8 C9 -0.5(3) . . . . ?
C12 C7 C8 C9 -178.88(16) . . . . ?
C1 O1 C9 C8 -45.0(2) . . . . ?
C7 C8 C9 O1 30.5(2) . . . . ?
C8 C7 C12 F3 5.7(2) . . . . ?
C6 C7 C12 F3 -172.71(15) . . . . ?
C8 C7 C12 F2 126.43(19) . . . . ?
C6 C7 C12 F2 -52.0(2) . . . . ?
C8 C7 C12 F1 -114.11(19) . . . . ?
C6 C7 C12 F1 67.5(2) . . . . ?

_refine_diff_density_max         0.209
_refine_diff_density_min         -0.299
_refine_diff_density_rms         0.051

_shelxl_version_number           2014/6



